Competition of interactions and a new high-temperature phase of seleno­urea

The aggregation of molecules is usually associated with a specific type of interaction, which can be altered by thermodynamic conditions. Under normal conditions, the crystal structure of seleno­urea, SeC(NH₂)₂, phase α is trigonal, space group P3₁, Z = 27. Its large number of independent molecules (Z_α′ = 9) can be associated with the formation of an NH...N hydrogen bond substituting one of 36 independent NH...Se hydrogen bonds, which prevail among intermolecular interactions. Phase α approximates the trigonal structure with a threefold smaller unit cell (Z = 9), which in turn approximates another still threefold smaller unit cell (Z = 3). The temperature-induced transformations of seleno­urea have been characterized by calorimetry and by performing 21 single-crystal X-ray diffraction structural determinations as a function of temperature. At 381.0 K, phase α undergoes a first-order displacive transition to phase γ, with space group P3₁21 and Z reduced to 9, when the NH...N bond is broken and an NH...Se bond is formed in its place. Previously, an analogous competition was observed between NH...N and NH...O hydrogen bonds in high-pressure phase III of urea. The lattice vectors along the (001) plane in low- and high-temperature phases of seleno­urea are related by a similarity rule, while the lattice dimensions along direction c are not affected. This similarity rule also applies to the structures of phase γ and hypothetical phase δ (Z = 3). The thermally controlled transition between enantiomorphic phases of seleno­urea contrasts with its high-pressure transition at 0.21 GPa to a centrosymmetric phase β, where both the NH...Se and NH...N bonds are present. The compression and heating reduce the number of independent molecules from Z′ = 9 in phase α, to Z′ = 2 in phase β and to Z′ = 1.5 in phase γ.

Computing details

For all structures, data collection: CrysAlis PRO 1.171.40.67a (Rigaku OD, 2019); cell refinement: CrysAlis PRO 1.171.40.67a (Rigaku OD, 2019); data reduction: CrysAlis PRO 1.171.40.67a (Rigaku OD, 2019). Program(s) used to solve structure: SHELXD (Sheldrick, 2008) for phase_alpha_Selenourea_110K, phase_alpha_Selenourea_293K, phase_alpha_Selenourea_303K, phase_alpha_Selenourea_333K, phase_alpha_Selenourea_343K, phase_alpha_Selenourea_353K, phase_alpha_Selenourea_363K, phase_alpha_Selenourea_373K, phase_gamma_Selenourea_383K; SHELXS (Sheldrick, 2008) for phase_alpha_Selenourea_130K, phase_alpha_Selenourea_150K, phase_alpha_Selenourea_170K, phase_alpha_Selenourea_210K, phase_alpha_Selenourea_270K, phase_alpha_Selenourea_313K, phase_alpha_Selenourea_323K; SHELXT 2018/2 (Sheldrick, 2018) for phase_alpha_Selenourea_190K, phase_alpha_Selenourea_230K, phase_alpha_Selenourea_250K, phase_alpha_Selenourea_290K, phase_gamma_Selenourea_393K. For all structures, program(s) used to refine structure: SHELXL 2018/3 (Sheldrick, 2015); molecular graphics: Olex2 1.3 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.3 (Dolomanov et al., 2009).

Selenourea (phase_alpha_Selenourea_110K)

Crystal data

CH4N2Se	Dx = 2.150 Mg m^−3
Mr = 123.02	Cu Kα radiation, λ = 1.54184 Å
Trigonal, P31	Cell parameters from 6736 reflections
a = 15.1354 (1) Å	θ = 3.4–72.0°
c = 12.9308 (1) Å	µ = 11.51 mm^−1
V = 2565.33 (4) Å^3	T = 110 K
Z = 27	Plate, orange
F(000) = 1566	0.25 × 0.10 × 0.05 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	3849 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	3836 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.040
Detector resolution: 10.5384 pixels mm^-1	θmax = 72.4°, θmin = 3.4°
ω scans	h = −18→16
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −18→17
Tmin = 0.218, Tmax = 1.000	l = −14→13
6546 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.037	w = 1/[σ^2(Fo^2) + (0.0637P)^2 + 4.4956P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.100	(Δ/σ)max = 0.001
S = 1.12	Δρmax = 0.75 e Å^−3
3849 reflections	Δρmin = −1.84 e Å^−3
325 parameters	Absolute structure: Refined as a perfect inversion twin.
1 restraint	Absolute structure parameter: 0.5
Primary atom site location: dual

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component perfect inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	0.30691 (6)	0.35156 (7)	0.09667 (6)	0.0125 (2)
Se2	0.39775 (7)	0.35996 (7)	0.75778 (6)	0.0136 (2)
Se3	0.30521 (6)	0.26969 (6)	0.42640 (7)	0.0122 (2)
Se4	0.63152 (7)	0.60773 (7)	0.70782 (6)	0.0140 (2)
Se5	0.72047 (6)	0.69453 (6)	0.05215 (7)	0.0124 (2)
Se6	0.63317 (6)	0.70244 (7)	0.38394 (6)	0.0126 (2)
Se7	0.72785 (6)	0.37694 (7)	0.47721 (8)	0.0168 (2)
Se8	0.29852 (6)	0.69993 (6)	0.66392 (8)	0.0143 (2)
Se9	1.06916 (7)	1.02422 (7)	0.45218 (9)	0.0183 (2)
C6	0.7511 (6)	0.6921 (6)	0.3931 (6)	0.0126 (15)
C2	0.2605 (6)	0.3242 (6)	0.7543 (6)	0.0131 (16)
C9	0.9341 (6)	0.9954 (6)	0.4485 (7)	0.0156 (16)
C3	0.4179 (6)	0.4028 (6)	0.4156 (6)	0.0139 (16)
C1	0.3873 (7)	0.2903 (7)	0.0944 (7)	0.0172 (18)
N16	0.8070 (5)	0.7058 (6)	0.3097 (6)	0.0185 (15)
H16A	0.861903	0.702407	0.313928	0.022*
H16B	0.788441	0.718187	0.251105	0.022*
N21	0.2120 (5)	0.3217 (6)	0.8403 (6)	0.0206 (16)
H21A	0.149252	0.306815	0.837753	0.025*
H21B	0.243234	0.335052	0.898680	0.025*
N19	0.8889 (6)	1.0050 (6)	0.5321 (6)	0.0207 (15)
H19A	0.826645	0.991545	0.528912	0.025*
H19B	0.921880	1.024755	0.589459	0.025*
N29	0.8818 (6)	0.9649 (7)	0.3615 (6)	0.0266 (18)
H29A	0.819604	0.951807	0.359713	0.032*
H29B	0.909932	0.958261	0.306486	0.032*
N22	0.2125 (6)	0.3039 (7)	0.6655 (6)	0.031 (2)
H22A	0.149697	0.288985	0.663351	0.038*
H22B	0.243692	0.305411	0.609396	0.038*
N26	0.7806 (6)	0.6732 (6)	0.4823 (6)	0.0225 (16)
H26A	0.835660	0.669949	0.485662	0.027*
H26B	0.744808	0.664145	0.537020	0.027*
N11	0.4379 (5)	0.2919 (6)	0.0109 (6)	0.0165 (14)
H11A	0.473260	0.261747	0.010920	0.020*
H11B	0.435528	0.323145	−0.043676	0.020*
N12	0.3937 (6)	0.2405 (6)	0.1773 (6)	0.0246 (17)
H12A	0.429801	0.211141	0.174580	0.030*
H12B	0.361645	0.237844	0.233192	0.030*
N28	0.3912 (7)	0.5989 (7)	0.7519 (6)	0.0272 (19)
H28A	0.428382	0.570732	0.751822	0.033*
H28B	0.361942	0.601294	0.808040	0.033*
N25	0.5239 (6)	0.6261 (6)	0.1280 (6)	0.0200 (15)
H25A	0.458373	0.593297	0.125231	0.024*
H25B	0.554528	0.660039	0.182608	0.024*
N17	0.5405 (5)	0.2429 (6)	0.3884 (6)	0.0217 (16)
H17A	0.475920	0.200563	0.388090	0.026*
H17B	0.574263	0.259174	0.331432	0.026*
N18	0.4255 (6)	0.6331 (7)	0.5813 (6)	0.0285 (19)
H18A	0.462356	0.604475	0.583134	0.034*
H18B	0.418696	0.658344	0.524309	0.034*
N23	0.4782 (5)	0.4449 (5)	0.4977 (6)	0.0227 (16)
H23A	0.531089	0.504693	0.493009	0.027*
H23B	0.464162	0.412072	0.555240	0.027*
N14	0.6783 (6)	0.8030 (6)	0.6456 (6)	0.0266 (17)
H14A	0.705099	0.868003	0.652233	0.032*
H14B	0.642271	0.772826	0.591872	0.032*
N24	0.7476 (6)	0.7981 (5)	0.7987 (6)	0.0213 (16)
H24A	0.773829	0.863094	0.804009	0.026*
H24B	0.757622	0.764622	0.846570	0.026*
N27	0.5328 (6)	0.2558 (6)	0.5629 (6)	0.0251 (17)
H27A	0.468363	0.213301	0.560378	0.030*
H27B	0.561750	0.280744	0.621358	0.030*
N13	0.4394 (7)	0.4528 (6)	0.3284 (6)	0.0284 (18)
H13A	0.492332	0.512594	0.323910	0.034*
H13B	0.400689	0.425865	0.275460	0.034*
C7	0.5878 (6)	0.2830 (6)	0.4766 (7)	0.0159 (16)
C5	0.5781 (6)	0.6244 (6)	0.0476 (6)	0.0124 (15)
C8	0.3790 (7)	0.6382 (7)	0.6667 (7)	0.0192 (18)
C4	0.6923 (6)	0.7500 (7)	0.7175 (7)	0.0170 (17)
N15	0.5298 (5)	0.5721 (6)	−0.0352 (6)	0.0224 (16)
H15A	0.464216	0.539600	−0.036919	0.027*
H15B	0.563823	0.570318	−0.087673	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0119 (4)	0.0117 (4)	0.0155 (5)	0.0069 (3)	−0.0006 (3)	0.0003 (3)
Se2	0.0089 (4)	0.0140 (4)	0.0172 (5)	0.0054 (3)	−0.0003 (3)	0.0015 (3)
Se3	0.0109 (4)	0.0093 (4)	0.0156 (4)	0.0045 (3)	0.0005 (3)	−0.0002 (3)
Se4	0.0127 (4)	0.0100 (4)	0.0181 (5)	0.0049 (3)	0.0000 (3)	−0.0004 (3)
Se5	0.0095 (4)	0.0106 (4)	0.0172 (5)	0.0051 (3)	−0.0007 (3)	−0.0006 (3)
Se6	0.0107 (4)	0.0114 (4)	0.0166 (5)	0.0062 (3)	−0.0003 (3)	−0.0002 (3)
Se7	0.0101 (4)	0.0143 (4)	0.0188 (5)	0.0007 (3)	−0.0011 (3)	0.0008 (4)
Se8	0.0160 (4)	0.0131 (4)	0.0167 (5)	0.0093 (4)	−0.0015 (3)	−0.0008 (3)
Se9	0.0110 (4)	0.0210 (5)	0.0237 (5)	0.0085 (4)	0.0026 (3)	0.0062 (4)
C6	0.020 (4)	0.006 (3)	0.016 (4)	0.010 (3)	−0.001 (3)	−0.001 (3)
C2	0.008 (4)	0.011 (4)	0.016 (4)	0.002 (3)	−0.002 (3)	−0.002 (3)
C9	0.015 (4)	0.011 (4)	0.018 (4)	0.004 (3)	0.000 (3)	0.000 (3)
C3	0.014 (4)	0.012 (4)	0.014 (4)	0.005 (3)	−0.003 (3)	−0.002 (3)
C1	0.027 (5)	0.014 (4)	0.012 (4)	0.011 (4)	−0.003 (3)	−0.004 (3)
N16	0.013 (3)	0.027 (4)	0.018 (4)	0.012 (3)	0.004 (3)	0.007 (3)
N21	0.013 (3)	0.025 (4)	0.023 (4)	0.009 (3)	0.000 (3)	−0.001 (3)
N19	0.016 (3)	0.032 (4)	0.015 (4)	0.013 (3)	0.003 (3)	0.002 (3)
N29	0.023 (4)	0.038 (5)	0.018 (4)	0.015 (4)	0.004 (3)	−0.008 (3)
N22	0.020 (4)	0.060 (6)	0.020 (4)	0.024 (4)	−0.009 (3)	−0.016 (4)
N26	0.017 (4)	0.038 (4)	0.020 (4)	0.019 (3)	−0.003 (3)	−0.002 (3)
N11	0.017 (3)	0.022 (4)	0.017 (4)	0.015 (3)	0.004 (3)	0.004 (3)
N12	0.034 (4)	0.038 (5)	0.015 (4)	0.028 (4)	0.003 (3)	0.003 (3)
N28	0.036 (5)	0.040 (5)	0.023 (4)	0.032 (4)	0.010 (3)	0.015 (4)
N25	0.014 (3)	0.021 (4)	0.022 (4)	0.007 (3)	0.002 (3)	−0.005 (3)
N17	0.011 (3)	0.023 (4)	0.023 (4)	0.002 (3)	0.003 (3)	−0.002 (3)
N18	0.037 (5)	0.054 (6)	0.015 (4)	0.038 (5)	0.005 (3)	0.009 (4)
N23	0.018 (4)	0.014 (3)	0.027 (4)	0.002 (3)	−0.001 (3)	−0.004 (3)
N14	0.036 (5)	0.015 (4)	0.026 (4)	0.010 (3)	−0.006 (3)	0.000 (3)
N24	0.027 (4)	0.010 (3)	0.022 (4)	0.006 (3)	−0.002 (3)	0.002 (3)
N27	0.014 (4)	0.031 (4)	0.024 (4)	0.007 (3)	−0.002 (3)	−0.005 (3)
N13	0.036 (5)	0.011 (3)	0.022 (4)	0.000 (3)	−0.001 (3)	−0.002 (3)
C7	0.012 (4)	0.018 (4)	0.021 (4)	0.009 (3)	0.001 (3)	−0.001 (3)
C5	0.012 (4)	0.015 (4)	0.007 (4)	0.004 (3)	−0.005 (3)	−0.002 (3)
C8	0.021 (4)	0.030 (5)	0.014 (4)	0.019 (4)	0.006 (3)	0.000 (3)
C4	0.013 (4)	0.022 (4)	0.012 (4)	0.005 (3)	0.003 (3)	0.004 (3)
N15	0.010 (3)	0.034 (4)	0.017 (4)	0.007 (3)	0.000 (3)	−0.008 (3)

Geometric parameters (Å, º)

Se1—C1	1.863 (9)	N11—H11B	0.8600
Se2—C2	1.868 (8)	N12—H12A	0.8600
Se3—C3	1.885 (8)	N12—H12B	0.8600
Se4—C4	1.875 (9)	N28—H28A	0.8600
Se5—C5	1.868 (8)	N28—H28B	0.8600
Se6—C6	1.872 (8)	N28—C8	1.307 (12)
Se7—C7	1.871 (8)	N25—H25A	0.8600
Se8—C8	1.871 (9)	N25—H25B	0.8600
Se9—C9	1.865 (8)	N25—C5	1.332 (11)
C6—N16	1.321 (11)	N17—H17A	0.8600
C6—N26	1.319 (11)	N17—H17B	0.8600
C2—N21	1.322 (11)	N17—C7	1.321 (12)
C2—N22	1.310 (11)	N18—H18A	0.8600
C9—N19	1.326 (11)	N18—H18B	0.8600
C9—N29	1.319 (12)	N18—C8	1.333 (11)
C3—N23	1.336 (11)	N23—H23A	0.8600
C3—N13	1.304 (11)	N23—H23B	0.8600
C1—N11	1.317 (11)	N14—H14A	0.8600
C1—N12	1.341 (11)	N14—H14B	0.8600
N16—H16A	0.8600	N14—C4	1.314 (12)
N16—H16B	0.8600	N24—H24A	0.8600
N21—H21A	0.8600	N24—H24B	0.8600
N21—H21B	0.8600	N24—C4	1.312 (12)
N19—H19A	0.8600	N27—H27A	0.8600
N19—H19B	0.8600	N27—H27B	0.8600
N29—H29A	0.8600	N27—C7	1.329 (11)
N29—H29B	0.8600	N13—H13A	0.8600
N22—H22A	0.8600	N13—H13B	0.8600
N22—H22B	0.8600	C5—N15	1.315 (11)
N26—H26A	0.8600	N15—H15A	0.8600
N26—H26B	0.8600	N15—H15B	0.8600
N11—H11A	0.8600
N16—C6—Se6	119.8 (6)	C8—N28—H28B	120.0
N26—C6—Se6	120.9 (6)	H25A—N25—H25B	120.0
N26—C6—N16	119.2 (7)	C5—N25—H25A	120.0
N21—C2—Se2	120.6 (6)	C5—N25—H25B	120.0
N22—C2—Se2	119.7 (6)	H17A—N17—H17B	120.0
N22—C2—N21	119.7 (7)	C7—N17—H17A	120.0
N19—C9—Se9	121.3 (6)	C7—N17—H17B	120.0
N29—C9—Se9	120.0 (7)	H18A—N18—H18B	120.0
N29—C9—N19	118.7 (8)	C8—N18—H18A	120.0
N23—C3—Se3	119.2 (6)	C8—N18—H18B	120.0
N13—C3—Se3	120.9 (6)	C3—N23—H23A	120.0
N13—C3—N23	119.8 (7)	C3—N23—H23B	120.0
N11—C1—Se1	121.4 (6)	H23A—N23—H23B	120.0
N11—C1—N12	117.5 (8)	H14A—N14—H14B	120.0
N12—C1—Se1	121.0 (6)	C4—N14—H14A	120.0
C6—N16—H16A	120.0	C4—N14—H14B	120.0
C6—N16—H16B	120.0	H24A—N24—H24B	120.0
H16A—N16—H16B	120.0	C4—N24—H24A	120.0
C2—N21—H21A	120.0	C4—N24—H24B	120.0
C2—N21—H21B	120.0	H27A—N27—H27B	120.0
H21A—N21—H21B	120.0	C7—N27—H27A	120.0
C9—N19—H19A	120.0	C7—N27—H27B	120.0
C9—N19—H19B	120.0	C3—N13—H13A	120.0
H19A—N19—H19B	120.0	C3—N13—H13B	120.0
C9—N29—H29A	120.0	H13A—N13—H13B	120.0
C9—N29—H29B	120.0	N17—C7—Se7	120.0 (6)
H29A—N29—H29B	120.0	N17—C7—N27	118.1 (8)
C2—N22—H22A	120.0	N27—C7—Se7	121.8 (6)
C2—N22—H22B	120.0	N25—C5—Se5	120.7 (6)
H22A—N22—H22B	120.0	N15—C5—Se5	120.3 (6)
C6—N26—H26A	120.0	N15—C5—N25	119.0 (7)
C6—N26—H26B	120.0	N28—C8—Se8	121.2 (6)
H26A—N26—H26B	120.0	N28—C8—N18	118.3 (8)
C1—N11—H11A	120.0	N18—C8—Se8	120.5 (7)
C1—N11—H11B	120.0	N14—C4—Se4	121.2 (7)
H11A—N11—H11B	120.0	N24—C4—Se4	120.1 (6)
C1—N12—H12A	120.0	N24—C4—N14	118.7 (8)
C1—N12—H12B	120.0	C5—N15—H15A	120.0
H12A—N12—H12B	120.0	C5—N15—H15B	120.0
H28A—N28—H28B	120.0	H15A—N15—H15B	120.0
C8—N28—H28A	120.0

Selenourea (phase_alpha_Selenourea_130K)

Crystal data

CH4N2Se	Dx = 2.145 Mg m^−3
Mr = 123.02	Cu Kα radiation, λ = 1.54184 Å
Trigonal, P31	Cell parameters from 6743 reflections
a = 15.14832 (11) Å	θ = 3.4–72.4°
c = 12.93947 (13) Å	µ = 11.49 mm^−1
V = 2571.44 (5) Å^3	T = 130 K
Z = 27	Plate, orange
F(000) = 1566	0.25 × 0.10 × 0.05 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	3884 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	3869 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.032
Detector resolution: 10.5384 pixels mm^-1	θmax = 72.4°, θmin = 3.4°
ω scans	h = −18→17
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −18→18
Tmin = 0.189, Tmax = 1.000	l = −14→13
6643 measured reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0634P)^2 + 4.140P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.036	(Δ/σ)max < 0.001
wR(F^2) = 0.098	Δρmax = 1.57 e Å^−3
S = 1.12	Δρmin = −0.77 e Å^−3
3884 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
326 parameters	Extinction coefficient: 0.00044 (5)
1 restraint	Absolute structure: Refined as a perfect inversion twin.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.5
Hydrogen site location: inferred from neighbouring sites

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component perfect inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	0.30687 (6)	0.35156 (6)	0.09676 (6)	0.0144 (2)
Se2	0.39743 (7)	0.35999 (7)	0.75782 (6)	0.0153 (2)
Se3	0.30519 (6)	0.26987 (6)	0.42643 (6)	0.01408 (19)
Se4	0.63146 (7)	0.60775 (7)	0.70780 (6)	0.0159 (2)
Se5	0.72068 (6)	0.69452 (6)	0.05194 (6)	0.0145 (2)
Se6	0.63318 (6)	0.70236 (7)	0.38377 (6)	0.0144 (2)
Se7	0.72782 (6)	0.37690 (7)	0.47695 (8)	0.0198 (2)
Se8	0.29851 (6)	0.70000 (6)	0.66399 (8)	0.0168 (2)
Se9	1.06917 (7)	1.02484 (7)	0.45348 (9)	0.0212 (2)
C6	0.7519 (6)	0.6924 (5)	0.3930 (6)	0.0155 (15)
C2	0.2600 (6)	0.3237 (6)	0.7552 (6)	0.0162 (16)
C9	0.9341 (6)	0.9951 (6)	0.4500 (7)	0.0198 (17)
C3	0.4178 (6)	0.4021 (6)	0.4159 (6)	0.0171 (16)
C1	0.3875 (7)	0.2898 (6)	0.0945 (6)	0.0169 (17)
N16	0.8064 (5)	0.7049 (5)	0.3096 (6)	0.0216 (15)
H16A	0.860419	0.699776	0.313159	0.026*
H16B	0.788135	0.718088	0.251375	0.026*
N21	0.2117 (5)	0.3211 (6)	0.8404 (6)	0.0248 (16)
H21A	0.148877	0.305646	0.837830	0.030*
H21B	0.242976	0.334827	0.898762	0.030*
N19	0.8891 (6)	1.0056 (6)	0.5329 (6)	0.0276 (17)
H19A	0.827108	0.992773	0.529361	0.033*
H19B	0.921912	1.025372	0.590296	0.033*
N29	0.8815 (6)	0.9646 (7)	0.3628 (6)	0.0323 (19)
H29A	0.819566	0.952130	0.360945	0.039*
H29B	0.909339	0.957263	0.308011	0.039*
N22	0.2117 (6)	0.3027 (8)	0.6663 (6)	0.037 (2)
H22A	0.148829	0.287257	0.664243	0.044*
H22B	0.242928	0.304272	0.610261	0.044*
N26	0.7799 (6)	0.6722 (6)	0.4818 (6)	0.0264 (16)
H26A	0.833911	0.667157	0.485348	0.032*
H26B	0.744295	0.664085	0.536430	0.032*
N11	0.4376 (5)	0.2916 (5)	0.0108 (5)	0.0193 (14)
H11A	0.473127	0.261661	0.010432	0.023*
H11B	0.434749	0.322656	−0.043664	0.023*
N12	0.3939 (6)	0.2408 (7)	0.1773 (6)	0.0297 (18)
H12A	0.429951	0.211462	0.175001	0.036*
H12B	0.361852	0.238486	0.233080	0.036*
N28	0.3905 (7)	0.5982 (7)	0.7524 (7)	0.0330 (19)
H28A	0.427379	0.569751	0.752151	0.040*
H28B	0.361275	0.600560	0.808462	0.040*
N25	0.5237 (6)	0.6257 (6)	0.1281 (6)	0.0241 (16)
H25A	0.458167	0.592405	0.125582	0.029*
H25B	0.554201	0.659359	0.182860	0.029*
N17	0.5404 (5)	0.2428 (6)	0.3888 (6)	0.0251 (16)
H17A	0.475994	0.200087	0.388252	0.030*
H17B	0.574299	0.259409	0.331890	0.030*
N18	0.4252 (7)	0.6328 (7)	0.5814 (6)	0.033 (2)
H18A	0.461638	0.603795	0.583773	0.040*
H18B	0.419011	0.658105	0.524223	0.040*
N23	0.4783 (5)	0.4451 (6)	0.4978 (6)	0.0251 (15)
H23A	0.530412	0.505330	0.492860	0.030*
H23B	0.465112	0.412453	0.555291	0.030*
N14	0.6784 (7)	0.8027 (6)	0.6450 (6)	0.0319 (18)
H14A	0.705415	0.867593	0.651562	0.038*
H14B	0.642744	0.772539	0.591144	0.038*
N24	0.7466 (6)	0.7975 (5)	0.7994 (6)	0.0258 (17)
H24A	0.772966	0.862480	0.804519	0.031*
H24B	0.756019	0.764009	0.847600	0.031*
N27	0.5326 (6)	0.2551 (6)	0.5626 (6)	0.0303 (18)
H27A	0.468270	0.212325	0.560140	0.036*
H27B	0.561485	0.280111	0.621015	0.036*
N13	0.4393 (7)	0.4533 (6)	0.3290 (6)	0.034 (2)
H13A	0.491701	0.513439	0.325273	0.041*
H13B	0.401105	0.426612	0.275759	0.041*
C7	0.5872 (6)	0.2825 (6)	0.4767 (7)	0.0190 (16)
C5	0.5779 (6)	0.6250 (6)	0.0473 (6)	0.0155 (15)
C8	0.3785 (7)	0.6384 (7)	0.6662 (6)	0.0201 (17)
C4	0.6916 (6)	0.7492 (6)	0.7177 (6)	0.0188 (17)
N15	0.5299 (5)	0.5731 (6)	−0.0354 (6)	0.0254 (16)
H15A	0.464387	0.540169	−0.037024	0.030*
H15B	0.564010	0.572039	−0.088104	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0149 (4)	0.0155 (4)	0.0146 (5)	0.0090 (3)	−0.0004 (3)	0.0001 (3)
Se2	0.0122 (4)	0.0181 (4)	0.0156 (5)	0.0075 (3)	−0.0002 (3)	0.0013 (3)
Se3	0.0143 (4)	0.0126 (4)	0.0145 (4)	0.0062 (3)	0.0004 (3)	−0.0001 (3)
Se4	0.0164 (4)	0.0135 (4)	0.0165 (5)	0.0065 (3)	0.0000 (3)	−0.0003 (3)
Se5	0.0130 (4)	0.0141 (4)	0.0161 (5)	0.0066 (3)	−0.0011 (3)	−0.0008 (3)
Se6	0.0144 (4)	0.0149 (4)	0.0150 (4)	0.0082 (3)	−0.0002 (3)	−0.0002 (3)
Se7	0.0138 (4)	0.0187 (4)	0.0190 (5)	0.0021 (3)	−0.0012 (3)	0.0008 (3)
Se8	0.0208 (4)	0.0172 (4)	0.0159 (5)	0.0122 (3)	−0.0017 (3)	−0.0009 (3)
Se9	0.0149 (4)	0.0262 (5)	0.0231 (5)	0.0107 (4)	0.0029 (3)	0.0071 (4)
C6	0.019 (4)	0.011 (3)	0.021 (4)	0.010 (3)	−0.001 (3)	−0.002 (3)
C2	0.014 (4)	0.019 (4)	0.017 (4)	0.009 (3)	−0.002 (3)	−0.001 (3)
C9	0.020 (4)	0.017 (4)	0.024 (5)	0.010 (3)	0.004 (3)	0.001 (3)
C3	0.020 (4)	0.018 (4)	0.012 (4)	0.008 (3)	−0.002 (3)	−0.006 (3)
C1	0.025 (4)	0.016 (4)	0.012 (4)	0.012 (3)	0.000 (3)	−0.002 (3)
N16	0.019 (3)	0.028 (4)	0.020 (4)	0.013 (3)	0.003 (3)	0.004 (3)
N21	0.019 (4)	0.035 (4)	0.021 (4)	0.015 (3)	0.000 (3)	−0.002 (3)
N19	0.022 (4)	0.044 (5)	0.022 (4)	0.022 (4)	0.002 (3)	0.000 (3)
N29	0.026 (4)	0.046 (5)	0.022 (4)	0.016 (4)	0.005 (3)	−0.008 (4)
N22	0.022 (4)	0.075 (7)	0.017 (4)	0.027 (4)	−0.005 (3)	−0.012 (4)
N26	0.023 (4)	0.051 (5)	0.017 (4)	0.027 (4)	−0.002 (3)	−0.001 (3)
N11	0.021 (3)	0.025 (4)	0.017 (4)	0.015 (3)	0.004 (3)	0.003 (3)
N12	0.041 (5)	0.049 (5)	0.015 (4)	0.034 (4)	0.005 (3)	0.006 (3)
N28	0.041 (5)	0.050 (5)	0.024 (4)	0.035 (4)	0.010 (4)	0.014 (4)
N25	0.021 (3)	0.026 (4)	0.023 (4)	0.010 (3)	0.005 (3)	−0.005 (3)
N17	0.014 (3)	0.027 (4)	0.026 (4)	0.003 (3)	0.002 (3)	0.001 (3)
N18	0.045 (5)	0.062 (6)	0.014 (4)	0.044 (5)	0.005 (3)	0.010 (4)
N23	0.021 (4)	0.022 (4)	0.025 (4)	0.006 (3)	0.000 (3)	0.000 (3)
N14	0.043 (5)	0.015 (3)	0.031 (4)	0.009 (3)	−0.011 (4)	0.000 (3)
N24	0.032 (4)	0.015 (3)	0.026 (4)	0.008 (3)	−0.001 (3)	0.004 (3)
N27	0.019 (4)	0.039 (5)	0.023 (4)	0.008 (3)	−0.002 (3)	−0.005 (3)
N13	0.049 (5)	0.014 (4)	0.022 (4)	0.002 (3)	0.002 (4)	0.001 (3)
C7	0.017 (4)	0.020 (4)	0.020 (4)	0.009 (3)	−0.003 (3)	−0.004 (3)
C5	0.015 (4)	0.021 (4)	0.010 (4)	0.008 (3)	−0.003 (3)	0.000 (3)
C8	0.029 (4)	0.034 (5)	0.008 (4)	0.023 (4)	0.002 (3)	−0.002 (3)
C4	0.020 (4)	0.021 (4)	0.013 (4)	0.008 (3)	0.006 (3)	0.003 (3)
N15	0.013 (3)	0.041 (4)	0.017 (4)	0.009 (3)	−0.004 (3)	−0.013 (3)

Geometric parameters (Å, º)

Se1—C1	1.874 (8)	N11—H11B	0.8600
Se2—C2	1.870 (8)	N12—H12A	0.8600
Se3—C3	1.877 (8)	N12—H12B	0.8600
Se4—C4	1.868 (9)	N28—H28A	0.8600
Se5—C5	1.874 (8)	N28—H28B	0.8600
Se6—C6	1.883 (7)	N28—C8	1.325 (11)
Se7—C7	1.881 (8)	N25—H25A	0.8600
Se8—C8	1.863 (8)	N25—H25B	0.8600
Se9—C9	1.863 (8)	N25—C5	1.333 (11)
C6—N16	1.315 (11)	N17—H17A	0.8600
C6—N26	1.313 (11)	N17—H17B	0.8600
C2—N21	1.312 (11)	N17—C7	1.316 (12)
C2—N22	1.313 (11)	N18—H18A	0.8600
C9—N19	1.321 (11)	N18—H18B	0.8600
C9—N29	1.324 (12)	N18—C8	1.331 (11)
C3—N23	1.337 (11)	N23—H23A	0.8600
C3—N13	1.311 (11)	N23—H23B	0.8600
C1—N11	1.315 (11)	N14—H14A	0.8600
C1—N12	1.335 (11)	N14—H14B	0.8600
N16—H16A	0.8600	N14—C4	1.319 (11)
N16—H16B	0.8600	N24—H24A	0.8600
N21—H21A	0.8600	N24—H24B	0.8600
N21—H21B	0.8600	N24—C4	1.318 (12)
N19—H19A	0.8600	N27—H27A	0.8600
N19—H19B	0.8600	N27—H27B	0.8600
N29—H29A	0.8600	N27—C7	1.323 (12)
N29—H29B	0.8600	N13—H13A	0.8600
N22—H22A	0.8600	N13—H13B	0.8600
N22—H22B	0.8600	C5—N15	1.312 (11)
N26—H26A	0.8600	N15—H15A	0.8600
N26—H26B	0.8600	N15—H15B	0.8600
N11—H11A	0.8600
N16—C6—Se6	119.5 (6)	C8—N28—H28B	120.0
N26—C6—Se6	120.5 (6)	H25A—N25—H25B	120.0
N26—C6—N16	120.0 (7)	C5—N25—H25A	120.0
N21—C2—Se2	121.0 (6)	C5—N25—H25B	120.0
N21—C2—N22	119.6 (7)	H17A—N17—H17B	120.0
N22—C2—Se2	119.4 (6)	C7—N17—H17A	120.0
N19—C9—Se9	121.4 (6)	C7—N17—H17B	120.0
N19—C9—N29	118.5 (8)	H18A—N18—H18B	120.0
N29—C9—Se9	120.0 (6)	C8—N18—H18A	120.0
N23—C3—Se3	119.9 (6)	C8—N18—H18B	120.0
N13—C3—Se3	121.2 (6)	C3—N23—H23A	120.0
N13—C3—N23	119.0 (7)	C3—N23—H23B	120.0
N11—C1—Se1	121.1 (6)	H23A—N23—H23B	120.0
N11—C1—N12	118.2 (7)	H14A—N14—H14B	120.0
N12—C1—Se1	120.8 (6)	C4—N14—H14A	120.0
C6—N16—H16A	120.0	C4—N14—H14B	120.0
C6—N16—H16B	120.0	H24A—N24—H24B	120.0
H16A—N16—H16B	120.0	C4—N24—H24A	120.0
C2—N21—H21A	120.0	C4—N24—H24B	120.0
C2—N21—H21B	120.0	H27A—N27—H27B	120.0
H21A—N21—H21B	120.0	C7—N27—H27A	120.0
C9—N19—H19A	120.0	C7—N27—H27B	120.0
C9—N19—H19B	120.0	C3—N13—H13A	120.0
H19A—N19—H19B	120.0	C3—N13—H13B	120.0
C9—N29—H29A	120.0	H13A—N13—H13B	120.0
C9—N29—H29B	120.0	N17—C7—Se7	119.7 (6)
H29A—N29—H29B	120.0	N17—C7—N27	118.3 (8)
C2—N22—H22A	120.0	N27—C7—Se7	122.0 (6)
C2—N22—H22B	120.0	N25—C5—Se5	120.8 (6)
H22A—N22—H22B	120.0	N15—C5—Se5	120.0 (6)
C6—N26—H26A	120.0	N15—C5—N25	119.1 (7)
C6—N26—H26B	120.0	N28—C8—Se8	121.0 (6)
H26A—N26—H26B	120.0	N28—C8—N18	117.7 (8)
C1—N11—H11A	120.0	N18—C8—Se8	121.3 (6)
C1—N11—H11B	120.0	N14—C4—Se4	121.2 (7)
H11A—N11—H11B	120.0	N24—C4—Se4	120.1 (6)
C1—N12—H12A	120.0	N24—C4—N14	118.6 (8)
C1—N12—H12B	120.0	C5—N15—H15A	120.0
H12A—N12—H12B	120.0	C5—N15—H15B	120.0
H28A—N28—H28B	120.0	H15A—N15—H15B	120.0
C8—N28—H28A	120.0

Selenourea (phase_alpha_Selenourea_150K)

Crystal data

CH4N2Se	Dx = 2.140 Mg m^−3
Mr = 123.02	Cu Kα radiation, λ = 1.54184 Å
Trigonal, P31	Cell parameters from 6761 reflections
a = 15.16245 (9) Å	θ = 3.4–72.2°
c = 12.94774 (11) Å	µ = 11.46 mm^−1
V = 2577.89 (4) Å^3	T = 150 K
Z = 27	Plate, orange
F(000) = 1566	0.25 × 0.10 × 0.05 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	4445 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	4440 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.019
Detector resolution: 10.5384 pixels mm^-1	θmax = 72.4°, θmin = 3.4°
ω scans	h = −18→16
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −18→17
Tmin = 0.291, Tmax = 0.564	l = −14→13
7392 measured reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0317P)^2 + 3.3746P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.023	(Δ/σ)max = 0.001
wR(F^2) = 0.065	Δρmax = 0.74 e Å^−3
S = 1.13	Δρmin = −0.51 e Å^−3
4445 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
326 parameters	Extinction coefficient: 0.00040 (3)
1 restraint	Absolute structure: Refined as a perfect inversion twin.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.5
Hydrogen site location: inferred from neighbouring sites

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component perfect inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	0.30678 (5)	0.35154 (5)	0.09692 (5)	0.01748 (15)
Se2	0.39715 (5)	0.36000 (5)	0.75795 (5)	0.01852 (15)
Se3	0.30514 (5)	0.26989 (5)	0.42647 (5)	0.01733 (14)
Se4	0.63137 (5)	0.60757 (5)	0.70759 (5)	0.01921 (16)
Se5	0.72074 (5)	0.69442 (5)	0.05182 (5)	0.01760 (15)
Se6	0.63320 (5)	0.70231 (5)	0.38371 (5)	0.01752 (15)
Se7	0.72790 (5)	0.37689 (5)	0.47674 (6)	0.02375 (17)
Se8	0.29846 (5)	0.70001 (5)	0.66376 (6)	0.02029 (17)
Se9	1.06937 (5)	1.02531 (5)	0.45448 (7)	0.02527 (16)
C6	0.7513 (4)	0.6916 (4)	0.3927 (5)	0.0193 (12)
C2	0.2595 (4)	0.3230 (5)	0.7549 (5)	0.0211 (13)
C9	0.9335 (5)	0.9946 (5)	0.4509 (5)	0.0227 (13)
C3	0.4171 (5)	0.4027 (4)	0.4162 (5)	0.0217 (13)
C1	0.3876 (5)	0.2895 (5)	0.0946 (5)	0.0196 (13)
N16	0.8065 (4)	0.7043 (4)	0.3096 (4)	0.0260 (12)
H16A	0.860344	0.699179	0.313646	0.031*
H16B	0.788608	0.717700	0.251313	0.031*
N21	0.2112 (4)	0.3199 (4)	0.8407 (5)	0.0286 (12)
H21A	0.148139	0.303431	0.838529	0.034*
H21B	0.242852	0.334278	0.898819	0.034*
N19	0.8893 (4)	1.0057 (5)	0.5331 (5)	0.0312 (13)
H19A	0.827641	0.993636	0.529498	0.037*
H19B	0.922048	1.024999	0.590525	0.037*
N29	0.8815 (4)	0.9650 (5)	0.3640 (5)	0.0373 (15)
H29A	0.819919	0.953274	0.361988	0.045*
H29B	0.909219	0.957279	0.309377	0.045*
N22	0.2108 (5)	0.3011 (6)	0.6672 (5)	0.0431 (17)
H22A	0.147746	0.284670	0.665607	0.052*
H22B	0.241838	0.302946	0.610888	0.052*
N26	0.7793 (4)	0.6712 (5)	0.4813 (4)	0.0320 (13)
H26A	0.833223	0.666231	0.484723	0.038*
H26B	0.743605	0.662887	0.535880	0.038*
N11	0.4370 (4)	0.2918 (4)	0.0108 (4)	0.0238 (11)
H11A	0.472774	0.262195	0.009833	0.029*
H11B	0.433727	0.322966	−0.043324	0.029*
N12	0.3934 (5)	0.2412 (5)	0.1774 (4)	0.0326 (14)
H12A	0.429399	0.211766	0.175649	0.039*
H12B	0.361241	0.239186	0.232836	0.039*
N28	0.3896 (5)	0.5977 (5)	0.7515 (5)	0.0396 (16)
H28A	0.426393	0.569223	0.751215	0.047*
H28B	0.360245	0.599833	0.807546	0.047*
N25	0.5247 (4)	0.6263 (4)	0.1278 (4)	0.0273 (12)
H25A	0.459272	0.593194	0.125569	0.033*
H25B	0.555592	0.660146	0.182216	0.033*
N17	0.5412 (4)	0.2426 (4)	0.3890 (5)	0.0316 (14)
H17A	0.476921	0.199702	0.388862	0.038*
H17B	0.574887	0.258550	0.332024	0.038*
N18	0.4251 (5)	0.6331 (6)	0.5811 (5)	0.0397 (16)
H18A	0.461455	0.604052	0.583138	0.048*
H18B	0.419051	0.658792	0.524174	0.048*
N23	0.4773 (4)	0.4453 (4)	0.4971 (5)	0.0294 (12)
H23A	0.529354	0.505497	0.492102	0.035*
H23B	0.464354	0.412711	0.554596	0.035*
N14	0.6781 (5)	0.8020 (4)	0.6446 (5)	0.0367 (15)
H14A	0.705058	0.866901	0.650397	0.044*
H14B	0.642346	0.771318	0.590956	0.044*
N24	0.7460 (4)	0.7971 (4)	0.7991 (5)	0.0290 (13)
H24A	0.772672	0.862066	0.804200	0.035*
H24B	0.755188	0.763541	0.847400	0.035*
N27	0.5334 (4)	0.2568 (5)	0.5617 (5)	0.0346 (14)
H27A	0.469141	0.213728	0.559466	0.042*
H27B	0.562269	0.282542	0.619767	0.042*
N13	0.4376 (5)	0.4531 (4)	0.3288 (5)	0.0397 (16)
H13A	0.489762	0.513311	0.324311	0.048*
H13B	0.398881	0.425982	0.275999	0.048*
C7	0.5878 (5)	0.2833 (4)	0.4756 (5)	0.0218 (13)
C5	0.5782 (4)	0.6251 (5)	0.0470 (5)	0.0202 (12)
C8	0.3782 (5)	0.6381 (5)	0.6662 (5)	0.0248 (14)
C4	0.6914 (5)	0.7493 (5)	0.7180 (5)	0.0225 (13)
N15	0.5301 (4)	0.5729 (5)	−0.0362 (4)	0.0323 (14)
H15A	0.464662	0.539962	−0.037934	0.039*
H15B	0.564299	0.571816	−0.088747	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0174 (3)	0.0180 (3)	0.0188 (4)	0.0102 (3)	−0.0007 (2)	0.0004 (2)
Se2	0.0144 (3)	0.0205 (3)	0.0204 (4)	0.0085 (3)	−0.0001 (3)	0.0020 (2)
Se3	0.0172 (3)	0.0147 (3)	0.0193 (3)	0.0074 (2)	0.0006 (2)	0.0002 (3)
Se4	0.0189 (3)	0.0151 (3)	0.0217 (4)	0.0071 (2)	0.0002 (3)	−0.0001 (2)
Se5	0.0154 (3)	0.0164 (3)	0.0208 (4)	0.0078 (2)	−0.0010 (2)	−0.0004 (2)
Se6	0.0165 (3)	0.0173 (3)	0.0201 (3)	0.0094 (2)	0.0000 (3)	−0.0001 (2)
Se7	0.0165 (3)	0.0215 (3)	0.0237 (4)	0.0024 (3)	−0.0012 (3)	0.0004 (3)
Se8	0.0244 (3)	0.0198 (3)	0.0209 (4)	0.0142 (3)	−0.0018 (3)	−0.0007 (3)
Se9	0.0170 (3)	0.0302 (4)	0.0295 (4)	0.0125 (3)	0.0034 (3)	0.0081 (3)
C6	0.022 (3)	0.015 (3)	0.024 (3)	0.011 (2)	−0.001 (2)	−0.003 (2)
C2	0.019 (3)	0.025 (3)	0.019 (3)	0.011 (2)	−0.001 (2)	−0.003 (3)
C9	0.019 (3)	0.021 (3)	0.026 (4)	0.009 (3)	0.006 (3)	0.003 (3)
C3	0.025 (3)	0.021 (3)	0.016 (3)	0.009 (3)	0.001 (2)	−0.004 (2)
C1	0.022 (3)	0.021 (3)	0.017 (3)	0.011 (3)	−0.001 (2)	−0.001 (2)
N16	0.020 (2)	0.034 (3)	0.027 (3)	0.016 (2)	0.005 (2)	0.005 (2)
N21	0.019 (3)	0.042 (3)	0.026 (3)	0.016 (2)	−0.001 (2)	−0.004 (3)
N19	0.024 (3)	0.048 (4)	0.027 (3)	0.023 (3)	0.001 (2)	−0.002 (3)
N29	0.023 (3)	0.054 (4)	0.030 (4)	0.016 (3)	0.000 (3)	−0.011 (3)
N22	0.024 (3)	0.080 (5)	0.029 (4)	0.029 (3)	−0.007 (3)	−0.013 (3)
N26	0.031 (3)	0.060 (4)	0.020 (3)	0.034 (3)	0.001 (2)	0.003 (3)
N11	0.027 (3)	0.033 (3)	0.019 (3)	0.020 (2)	0.006 (2)	0.007 (2)
N12	0.044 (3)	0.050 (4)	0.023 (3)	0.038 (3)	0.005 (3)	0.004 (3)
N28	0.055 (4)	0.059 (4)	0.032 (4)	0.049 (4)	0.015 (3)	0.014 (3)
N25	0.022 (3)	0.027 (3)	0.029 (3)	0.009 (2)	0.001 (2)	−0.006 (2)
N17	0.017 (3)	0.033 (3)	0.031 (4)	0.002 (2)	0.004 (2)	−0.001 (3)
N18	0.051 (4)	0.075 (5)	0.019 (3)	0.051 (4)	0.009 (3)	0.015 (3)
N23	0.024 (3)	0.022 (3)	0.029 (3)	0.002 (2)	−0.001 (2)	−0.002 (2)
N14	0.059 (4)	0.022 (3)	0.027 (3)	0.019 (3)	−0.010 (3)	−0.002 (2)
N24	0.035 (3)	0.015 (3)	0.032 (3)	0.008 (2)	−0.002 (3)	0.000 (2)
N27	0.019 (3)	0.047 (4)	0.029 (4)	0.010 (3)	−0.002 (2)	−0.005 (3)
N13	0.053 (4)	0.019 (3)	0.025 (3)	0.001 (3)	−0.002 (3)	0.002 (2)
C7	0.021 (3)	0.021 (3)	0.023 (3)	0.011 (3)	−0.002 (2)	−0.003 (2)
C5	0.020 (3)	0.019 (3)	0.020 (3)	0.009 (2)	−0.001 (2)	−0.001 (2)
C8	0.028 (3)	0.037 (4)	0.017 (3)	0.022 (3)	0.003 (3)	0.004 (3)
C4	0.024 (3)	0.024 (3)	0.020 (3)	0.013 (3)	0.006 (2)	0.000 (3)
N15	0.019 (3)	0.048 (4)	0.022 (3)	0.010 (2)	0.000 (2)	−0.010 (3)

Geometric parameters (Å, º)

Se1—C1	1.881 (6)	N11—H11B	0.8600
Se2—C2	1.872 (6)	N12—H12A	0.8600
Se3—C3	1.881 (6)	N12—H12B	0.8600
Se4—C4	1.873 (6)	N28—H28A	0.8600
Se5—C5	1.873 (6)	N28—H28B	0.8600
Se6—C6	1.881 (6)	N28—C8	1.315 (9)
Se7—C7	1.875 (6)	N25—H25A	0.8600
Se8—C8	1.864 (6)	N25—H25B	0.8600
Se9—C9	1.871 (6)	N25—C5	1.329 (8)
C6—N16	1.317 (8)	N17—H17A	0.8600
C6—N26	1.311 (8)	N17—H17B	0.8600
C2—N21	1.318 (8)	N17—C7	1.304 (9)
C2—N22	1.303 (9)	N18—H18A	0.8600
C9—N19	1.312 (9)	N18—H18B	0.8600
C9—N29	1.317 (9)	N18—C8	1.336 (9)
C3—N23	1.326 (8)	N23—H23A	0.8600
C3—N13	1.313 (9)	N23—H23B	0.8600
C1—N11	1.309 (8)	N14—H14A	0.8600
C1—N12	1.327 (8)	N14—H14B	0.8600
N16—H16A	0.8600	N14—C4	1.320 (9)
N16—H16B	0.8600	N24—H24A	0.8600
N21—H21A	0.8600	N24—H24B	0.8600
N21—H21B	0.8600	N24—C4	1.309 (9)
N19—H19A	0.8600	N27—H27A	0.8600
N19—H19B	0.8600	N27—H27B	0.8600
N29—H29A	0.8600	N27—C7	1.323 (9)
N29—H29B	0.8600	N13—H13A	0.8600
N22—H22A	0.8600	N13—H13B	0.8600
N22—H22B	0.8600	C5—N15	1.320 (8)
N26—H26A	0.8600	N15—H15A	0.8600
N26—H26B	0.8600	N15—H15B	0.8600
N11—H11A	0.8600
N16—C6—Se6	119.9 (5)	C8—N28—H28B	120.0
N26—C6—Se6	120.6 (5)	H25A—N25—H25B	120.0
N26—C6—N16	119.5 (5)	C5—N25—H25A	120.0
N21—C2—Se2	120.6 (5)	C5—N25—H25B	120.0
N22—C2—Se2	119.9 (5)	H17A—N17—H17B	120.0
N22—C2—N21	119.5 (6)	C7—N17—H17A	120.0
N19—C9—Se9	121.2 (5)	C7—N17—H17B	120.0
N19—C9—N29	118.6 (6)	H18A—N18—H18B	120.0
N29—C9—Se9	120.1 (5)	C8—N18—H18A	120.0
N23—C3—Se3	119.9 (5)	C8—N18—H18B	120.0
N13—C3—Se3	120.6 (5)	C3—N23—H23A	120.0
N13—C3—N23	119.5 (6)	C3—N23—H23B	120.0
N11—C1—Se1	120.5 (5)	H23A—N23—H23B	120.0
N11—C1—N12	119.3 (6)	H14A—N14—H14B	120.0
N12—C1—Se1	120.2 (5)	C4—N14—H14A	120.0
C6—N16—H16A	120.0	C4—N14—H14B	120.0
C6—N16—H16B	120.0	H24A—N24—H24B	120.0
H16A—N16—H16B	120.0	C4—N24—H24A	120.0
C2—N21—H21A	120.0	C4—N24—H24B	120.0
C2—N21—H21B	120.0	H27A—N27—H27B	120.0
H21A—N21—H21B	120.0	C7—N27—H27A	120.0
C9—N19—H19A	120.0	C7—N27—H27B	120.0
C9—N19—H19B	120.0	C3—N13—H13A	120.0
H19A—N19—H19B	120.0	C3—N13—H13B	120.0
C9—N29—H29A	120.0	H13A—N13—H13B	120.0
C9—N29—H29B	120.0	N17—C7—Se7	120.3 (5)
H29A—N29—H29B	120.0	N17—C7—N27	118.2 (6)
C2—N22—H22A	120.0	N27—C7—Se7	121.4 (5)
C2—N22—H22B	120.0	N25—C5—Se5	120.4 (5)
H22A—N22—H22B	120.0	N15—C5—Se5	120.0 (5)
C6—N26—H26A	120.0	N15—C5—N25	119.6 (6)
C6—N26—H26B	120.0	N28—C8—Se8	121.2 (5)
H26A—N26—H26B	120.0	N28—C8—N18	117.9 (6)
C1—N11—H11A	120.0	N18—C8—Se8	120.9 (5)
C1—N11—H11B	120.0	N14—C4—Se4	120.6 (5)
H11A—N11—H11B	120.0	N24—C4—Se4	120.2 (5)
C1—N12—H12A	120.0	N24—C4—N14	119.3 (6)
C1—N12—H12B	120.0	C5—N15—H15A	120.0
H12A—N12—H12B	120.0	C5—N15—H15B	120.0
H28A—N28—H28B	120.0	H15A—N15—H15B	120.0
C8—N28—H28A	120.0

Selenourea (phase_alpha_Selenourea_170K)

Crystal data

CH4N2Se	Dx = 2.134 Mg m^−3
Mr = 123.02	Cu Kα radiation, λ = 1.54184 Å
Trigonal, P31	Cell parameters from 6746 reflections
a = 15.17648 (10) Å	θ = 3.4–72.1°
c = 12.95625 (12) Å	µ = 11.43 mm^−1
V = 2584.35 (4) Å^3	T = 170 K
Z = 27	Plate, orange
F(000) = 1566	0.25 × 0.10 × 0.05 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	4459 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	4448 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.020
Detector resolution: 10.5384 pixels mm^-1	θmax = 72.2°, θmin = 3.4°
ω scans	h = −18→17
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −18→18
Tmin = 0.193, Tmax = 1.000	l = −14→13
7405 measured reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0368P)^2 + 2.7838P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.025	(Δ/σ)max = 0.001
wR(F^2) = 0.069	Δρmax = 0.79 e Å^−3
S = 1.11	Δρmin = −0.58 e Å^−3
4459 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
326 parameters	Extinction coefficient: 0.00047 (3)
1 restraint	Absolute structure: Refined as a perfect inversion twin.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.5
Hydrogen site location: inferred from neighbouring sites

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component perfect inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	0.30672 (5)	0.35149 (5)	0.09698 (5)	0.01991 (15)
Se2	0.39680 (5)	0.36003 (5)	0.75797 (5)	0.02087 (15)
Se3	0.30504 (5)	0.26999 (5)	0.42644 (5)	0.01957 (14)
Se4	0.63129 (5)	0.60749 (5)	0.70746 (5)	0.02163 (16)
Se5	0.72080 (5)	0.69430 (5)	0.05159 (5)	0.01984 (15)
Se6	0.63328 (5)	0.70225 (5)	0.38356 (5)	0.01977 (15)
Se7	0.72795 (5)	0.37686 (5)	0.47637 (6)	0.02686 (18)
Se8	0.29844 (5)	0.70000 (5)	0.66372 (6)	0.02298 (17)
Se9	1.06947 (5)	1.02587 (5)	0.45562 (7)	0.02830 (17)
C6	0.7507 (4)	0.6911 (4)	0.3927 (5)	0.0226 (12)
C2	0.2590 (5)	0.3222 (5)	0.7550 (5)	0.0236 (13)
C9	0.9337 (5)	0.9950 (5)	0.4520 (5)	0.0256 (13)
C3	0.4169 (5)	0.4027 (5)	0.4166 (5)	0.0245 (13)
C1	0.3873 (5)	0.2892 (5)	0.0948 (5)	0.0216 (13)
N16	0.8061 (4)	0.7037 (4)	0.3098 (4)	0.0297 (12)
H16A	0.859769	0.698407	0.313946	0.036*
H16B	0.788530	0.717366	0.251433	0.036*
N21	0.2111 (4)	0.3192 (5)	0.8408 (5)	0.0322 (13)
H21A	0.147991	0.302513	0.838935	0.039*
H21B	0.242967	0.333964	0.898787	0.039*
N19	0.8896 (4)	1.0059 (5)	0.5337 (5)	0.0352 (13)
H19A	0.827782	0.993379	0.530095	0.042*
H19B	0.922306	1.025504	0.590994	0.042*
N29	0.8819 (5)	0.9648 (5)	0.3650 (5)	0.0423 (16)
H29A	0.820164	0.952639	0.362699	0.051*
H29B	0.909840	0.957291	0.310483	0.051*
N22	0.2104 (5)	0.2998 (6)	0.6676 (5)	0.0490 (19)
H22A	0.147252	0.283175	0.666102	0.059*
H22B	0.241330	0.301699	0.611382	0.059*
N26	0.7787 (5)	0.6703 (5)	0.4810 (4)	0.0363 (14)
H26A	0.832541	0.665154	0.484262	0.044*
H26B	0.743165	0.661857	0.535708	0.044*
N11	0.4367 (4)	0.2916 (4)	0.0108 (4)	0.0274 (12)
H11A	0.472831	0.262457	0.009883	0.033*
H11B	0.432953	0.322372	−0.043332	0.033*
N12	0.3935 (5)	0.2416 (5)	0.1778 (4)	0.0358 (14)
H12A	0.429783	0.212603	0.176426	0.043*
H12B	0.361296	0.239771	0.233139	0.043*
N28	0.3889 (5)	0.5972 (6)	0.7511 (5)	0.0440 (17)
H28A	0.425477	0.568523	0.750668	0.053*
H28B	0.359442	0.599088	0.807087	0.053*
N25	0.5251 (4)	0.6265 (4)	0.1281 (5)	0.0309 (12)
H25A	0.459749	0.593589	0.125964	0.037*
H25B	0.556088	0.660093	0.182582	0.037*
N17	0.5414 (4)	0.2427 (5)	0.3885 (5)	0.0360 (14)
H17A	0.477115	0.200082	0.388307	0.043*
H17B	0.575096	0.258557	0.331605	0.043*
N18	0.4250 (5)	0.6336 (6)	0.5812 (5)	0.0465 (18)
H18A	0.461069	0.604446	0.583073	0.056*
H18B	0.419216	0.659829	0.524548	0.056*
N23	0.4766 (4)	0.4453 (4)	0.4972 (5)	0.0337 (13)
H23A	0.528312	0.505584	0.492246	0.040*
H23B	0.463675	0.412751	0.554646	0.040*
N14	0.6779 (5)	0.8015 (4)	0.6450 (5)	0.0420 (16)
H14A	0.704620	0.866324	0.651112	0.050*
H14B	0.642539	0.771067	0.591166	0.050*
N24	0.7452 (5)	0.7969 (4)	0.7990 (5)	0.0341 (14)
H24A	0.771414	0.861730	0.804045	0.041*
H24B	0.754456	0.763507	0.847300	0.041*
N27	0.5340 (4)	0.2575 (5)	0.5616 (5)	0.0397 (15)
H27A	0.469718	0.214717	0.559722	0.048*
H27B	0.563134	0.283443	0.619491	0.048*
N13	0.4372 (5)	0.4530 (5)	0.3291 (5)	0.0452 (17)
H13A	0.489040	0.513306	0.324655	0.054*
H13B	0.398570	0.425687	0.276382	0.054*
C7	0.5880 (5)	0.2835 (4)	0.4753 (5)	0.0243 (13)
C5	0.5784 (5)	0.6253 (5)	0.0472 (5)	0.0221 (12)
C8	0.3780 (5)	0.6383 (5)	0.6661 (5)	0.0274 (14)
C4	0.6911 (5)	0.7490 (5)	0.7178 (5)	0.0259 (14)
N15	0.5303 (4)	0.5734 (5)	−0.0362 (5)	0.0362 (14)
H15A	0.464865	0.540633	−0.037976	0.043*
H15B	0.564367	0.572339	−0.088796	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0200 (3)	0.0203 (3)	0.0214 (4)	0.0115 (3)	−0.0009 (2)	0.0001 (3)
Se2	0.0165 (3)	0.0233 (3)	0.0225 (4)	0.0097 (3)	0.0000 (3)	0.0023 (2)
Se3	0.0197 (3)	0.0167 (3)	0.0215 (3)	0.0084 (3)	0.0007 (2)	0.0004 (3)
Se4	0.0216 (3)	0.0171 (3)	0.0241 (4)	0.0081 (2)	0.0003 (3)	0.0000 (2)
Se5	0.0173 (3)	0.0188 (3)	0.0233 (4)	0.0089 (2)	−0.0011 (2)	−0.0004 (2)
Se6	0.0188 (3)	0.0200 (3)	0.0221 (4)	0.0109 (3)	−0.0001 (3)	0.0001 (2)
Se7	0.0187 (3)	0.0245 (3)	0.0266 (4)	0.0028 (3)	−0.0015 (3)	0.0005 (3)
Se8	0.0278 (3)	0.0226 (3)	0.0235 (4)	0.0163 (3)	−0.0019 (3)	−0.0009 (3)
Se9	0.0192 (3)	0.0340 (4)	0.0325 (4)	0.0140 (3)	0.0037 (3)	0.0089 (3)
C6	0.025 (3)	0.018 (3)	0.029 (3)	0.014 (2)	−0.001 (2)	−0.002 (2)
C2	0.022 (3)	0.029 (3)	0.020 (3)	0.013 (3)	0.000 (2)	−0.002 (3)
C9	0.024 (3)	0.022 (3)	0.030 (4)	0.010 (3)	0.007 (3)	0.004 (3)
C3	0.028 (3)	0.023 (3)	0.020 (3)	0.011 (3)	0.001 (3)	−0.005 (2)
C1	0.025 (3)	0.024 (3)	0.018 (3)	0.013 (3)	−0.002 (2)	−0.002 (2)
N16	0.024 (3)	0.040 (3)	0.029 (3)	0.019 (2)	0.004 (2)	0.004 (2)
N21	0.023 (3)	0.049 (3)	0.027 (3)	0.019 (3)	−0.002 (2)	−0.006 (3)
N19	0.029 (3)	0.056 (4)	0.028 (3)	0.028 (3)	0.001 (2)	−0.003 (3)
N29	0.025 (3)	0.062 (4)	0.033 (4)	0.016 (3)	0.000 (3)	−0.010 (3)
N22	0.027 (3)	0.096 (6)	0.028 (4)	0.034 (3)	−0.008 (3)	−0.014 (4)
N26	0.037 (3)	0.068 (4)	0.022 (3)	0.040 (3)	0.001 (2)	0.005 (3)
N11	0.030 (3)	0.036 (3)	0.023 (3)	0.022 (2)	0.006 (2)	0.006 (2)
N12	0.050 (4)	0.056 (4)	0.023 (3)	0.042 (3)	0.005 (3)	0.005 (3)
N28	0.060 (4)	0.066 (4)	0.036 (4)	0.054 (4)	0.016 (3)	0.017 (3)
N25	0.025 (3)	0.033 (3)	0.032 (3)	0.012 (2)	0.002 (2)	−0.007 (2)
N17	0.021 (3)	0.037 (3)	0.035 (4)	0.004 (2)	0.002 (2)	−0.005 (3)
N18	0.059 (4)	0.087 (5)	0.024 (3)	0.059 (4)	0.012 (3)	0.017 (3)
N23	0.029 (3)	0.024 (3)	0.034 (3)	0.002 (2)	−0.001 (2)	−0.002 (2)
N14	0.068 (4)	0.024 (3)	0.032 (3)	0.022 (3)	−0.013 (3)	−0.001 (2)
N24	0.041 (3)	0.018 (3)	0.035 (4)	0.008 (2)	−0.002 (3)	0.002 (2)
N27	0.020 (3)	0.050 (4)	0.036 (4)	0.008 (3)	−0.001 (2)	−0.003 (3)
N13	0.060 (4)	0.023 (3)	0.027 (3)	0.002 (3)	0.000 (3)	0.002 (2)
C7	0.022 (3)	0.024 (3)	0.026 (4)	0.011 (3)	−0.002 (2)	−0.002 (3)
C5	0.021 (3)	0.023 (3)	0.021 (3)	0.010 (2)	0.000 (2)	0.000 (2)
C8	0.028 (3)	0.041 (4)	0.020 (3)	0.022 (3)	0.000 (3)	0.001 (3)
C4	0.029 (3)	0.028 (3)	0.023 (3)	0.016 (3)	0.009 (3)	0.001 (3)
N15	0.021 (3)	0.051 (4)	0.029 (3)	0.012 (3)	−0.001 (2)	−0.012 (3)

Geometric parameters (Å, º)

Se1—C1	1.883 (6)	N11—H11B	0.8600
Se2—C2	1.873 (6)	N12—H12A	0.8600
Se3—C3	1.880 (6)	N12—H12B	0.8600
Se4—C4	1.872 (7)	N28—H28A	0.8600
Se5—C5	1.873 (6)	N28—H28B	0.8600
Se6—C6	1.877 (6)	N28—C8	1.316 (9)
Se7—C7	1.874 (6)	N25—H25A	0.8600
Se8—C8	1.862 (6)	N25—H25B	0.8600
Se9—C9	1.872 (6)	N25—C5	1.329 (8)
C6—N16	1.317 (8)	N17—H17A	0.8600
C6—N26	1.313 (8)	N17—H17B	0.8600
C2—N21	1.317 (8)	N17—C7	1.307 (9)
C2—N22	1.300 (9)	N18—H18A	0.8600
C9—N19	1.306 (9)	N18—H18B	0.8600
C9—N29	1.318 (9)	N18—C8	1.331 (9)
C3—N23	1.320 (8)	N23—H23A	0.8600
C3—N13	1.315 (9)	N23—H23B	0.8600
C1—N11	1.311 (8)	N14—H14A	0.8600
C1—N12	1.325 (8)	N14—H14B	0.8600
N16—H16A	0.8600	N14—C4	1.313 (9)
N16—H16B	0.8600	N24—H24A	0.8600
N21—H21A	0.8600	N24—H24B	0.8600
N21—H21B	0.8600	N24—C4	1.308 (9)
N19—H19A	0.8600	N27—H27A	0.8600
N19—H19B	0.8600	N27—H27B	0.8600
N29—H29A	0.8600	N27—C7	1.325 (9)
N29—H29B	0.8600	N13—H13A	0.8600
N22—H22A	0.8600	N13—H13B	0.8600
N22—H22B	0.8600	C5—N15	1.322 (9)
N26—H26A	0.8600	N15—H15A	0.8600
N26—H26B	0.8600	N15—H15B	0.8600
N11—H11A	0.8600
N16—C6—Se6	120.1 (5)	C8—N28—H28B	120.0
N26—C6—Se6	120.8 (5)	H25A—N25—H25B	120.0
N26—C6—N16	119.1 (5)	C5—N25—H25A	120.0
N21—C2—Se2	120.4 (5)	C5—N25—H25B	120.0
N22—C2—Se2	119.9 (5)	H17A—N17—H17B	120.0
N22—C2—N21	119.7 (6)	C7—N17—H17A	120.0
N19—C9—Se9	121.2 (5)	C7—N17—H17B	120.0
N19—C9—N29	118.8 (6)	H18A—N18—H18B	120.0
N29—C9—Se9	119.9 (5)	C8—N18—H18A	120.0
N23—C3—Se3	120.1 (5)	C8—N18—H18B	120.0
N13—C3—Se3	120.3 (5)	C3—N23—H23A	120.0
N13—C3—N23	119.6 (6)	C3—N23—H23B	120.0
N11—C1—Se1	120.3 (5)	H23A—N23—H23B	120.0
N11—C1—N12	119.6 (6)	H14A—N14—H14B	120.0
N12—C1—Se1	120.2 (5)	C4—N14—H14A	120.0
C6—N16—H16A	120.0	C4—N14—H14B	120.0
C6—N16—H16B	120.0	H24A—N24—H24B	120.0
H16A—N16—H16B	120.0	C4—N24—H24A	120.0
C2—N21—H21A	120.0	C4—N24—H24B	120.0
C2—N21—H21B	120.0	H27A—N27—H27B	120.0
H21A—N21—H21B	120.0	C7—N27—H27A	120.0
C9—N19—H19A	120.0	C7—N27—H27B	120.0
C9—N19—H19B	120.0	C3—N13—H13A	120.0
H19A—N19—H19B	120.0	C3—N13—H13B	120.0
C9—N29—H29A	120.0	H13A—N13—H13B	120.0
C9—N29—H29B	120.0	N17—C7—Se7	120.3 (5)
H29A—N29—H29B	120.0	N17—C7—N27	118.5 (6)
C2—N22—H22A	120.0	N27—C7—Se7	121.2 (5)
C2—N22—H22B	120.0	N25—C5—Se5	120.5 (5)
H22A—N22—H22B	120.0	N15—C5—Se5	119.8 (5)
C6—N26—H26A	120.0	N15—C5—N25	119.6 (6)
C6—N26—H26B	120.0	N28—C8—Se8	121.2 (5)
H26A—N26—H26B	120.0	N28—C8—N18	118.0 (6)
C1—N11—H11A	120.0	N18—C8—Se8	120.8 (5)
C1—N11—H11B	120.0	N14—C4—Se4	120.7 (5)
H11A—N11—H11B	120.0	N24—C4—Se4	120.3 (5)
C1—N12—H12A	120.0	N24—C4—N14	118.9 (6)
C1—N12—H12B	120.0	C5—N15—H15A	120.0
H12A—N12—H12B	120.0	C5—N15—H15B	120.0
H28A—N28—H28B	120.0	H15A—N15—H15B	120.0
C8—N28—H28A	120.0

Selenourea (phase_alpha_Selenourea_190K)

Crystal data

CH4N2Se	Dx = 2.128 Mg m^−3
Mr = 123.02	Cu Kα radiation, λ = 1.54184 Å
Trigonal, P31	Cell parameters from 6736 reflections
a = 15.1910 (1) Å	θ = 3.4–72.3°
c = 12.9669 (1) Å	µ = 11.40 mm^−1
V = 2591.43 (4) Å^3	T = 190 K
Z = 27	Plate, orange
F(000) = 1566	0.25 × 0.10 × 0.05 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	3945 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	3925 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.037
Detector resolution: 10.5384 pixels mm^-1	θmax = 72.5°, θmin = 3.4°
ω scans	h = −18→17
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −18→18
Tmin = 0.357, Tmax = 1.000	l = −14→13
6693 measured reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0643P)^2 + 0.9764P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.033	(Δ/σ)max < 0.001
wR(F^2) = 0.092	Δρmax = 0.93 e Å^−3
S = 1.08	Δρmin = −0.60 e Å^−3
3945 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
326 parameters	Extinction coefficient: 0.00057 (5)
1 restraint	Absolute structure: Refined as a perfect inversion twin.
Primary atom site location: dual	Absolute structure parameter: 0.5
Hydrogen site location: inferred from neighbouring sites

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component perfect inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	0.30657 (6)	0.35137 (6)	0.09706 (5)	0.02247 (18)
Se2	0.39638 (6)	0.35999 (6)	0.75795 (5)	0.02338 (19)
Se3	0.30500 (6)	0.27010 (5)	0.42643 (6)	0.02181 (18)
Se4	0.63111 (6)	0.60742 (6)	0.70730 (5)	0.0239 (2)
Se5	0.72083 (5)	0.69421 (5)	0.05141 (6)	0.02212 (18)
Se6	0.63330 (6)	0.70216 (6)	0.38338 (5)	0.02224 (18)
Se7	0.72802 (6)	0.37685 (7)	0.47603 (7)	0.0300 (2)
Se8	0.29840 (6)	0.70002 (5)	0.66368 (7)	0.0254 (2)
Se9	1.06957 (6)	1.02643 (7)	0.45665 (8)	0.0315 (2)
C6	0.7501 (5)	0.6907 (5)	0.3919 (6)	0.0240 (13)
C2	0.2585 (5)	0.3210 (6)	0.7557 (6)	0.0260 (15)
C9	0.9339 (5)	0.9957 (5)	0.4519 (6)	0.0274 (15)
C3	0.4157 (5)	0.4032 (5)	0.4167 (5)	0.0266 (15)
C1	0.3871 (6)	0.2897 (6)	0.0948 (6)	0.0251 (15)
N16	0.8056 (5)	0.7030 (5)	0.3098 (5)	0.0327 (14)
H16A	0.859012	0.697399	0.314513	0.039*
H16B	0.788492	0.716701	0.251337	0.039*
N21	0.2106 (5)	0.3185 (6)	0.8413 (5)	0.0364 (15)
H21A	0.147633	0.301954	0.839280	0.044*
H21B	0.242398	0.333345	0.899290	0.044*
N19	0.8901 (5)	1.0062 (6)	0.5346 (5)	0.0360 (15)
H19A	0.827972	0.992650	0.531912	0.043*
H19B	0.923538	1.026781	0.591407	0.043*
N29	0.8822 (5)	0.9645 (6)	0.3666 (6)	0.0436 (18)
H29A	0.820126	0.951139	0.364824	0.052*
H29B	0.910100	0.957292	0.311971	0.052*
N22	0.2106 (6)	0.2985 (8)	0.6681 (6)	0.058 (3)
H22A	0.147581	0.281993	0.666005	0.070*
H22B	0.241880	0.300166	0.612243	0.070*
N26	0.7782 (5)	0.6696 (6)	0.4811 (5)	0.0413 (17)
H26A	0.831914	0.664296	0.484286	0.050*
H26B	0.742767	0.661280	0.535717	0.050*
N11	0.4368 (5)	0.2920 (5)	0.0112 (5)	0.0309 (14)
H11A	0.472514	0.262365	0.010602	0.037*
H11B	0.433759	0.323003	−0.042904	0.037*
N12	0.3934 (6)	0.2411 (6)	0.1772 (5)	0.0405 (17)
H12A	0.429450	0.212008	0.175028	0.049*
H12B	0.361306	0.238783	0.232776	0.049*
N28	0.3878 (6)	0.5967 (7)	0.7505 (6)	0.048 (2)
H28A	0.424010	0.567684	0.749580	0.058*
H28B	0.358463	0.598301	0.806662	0.058*
N25	0.5249 (5)	0.6267 (5)	0.1272 (5)	0.0347 (15)
H25A	0.459588	0.593485	0.123922	0.042*
H25B	0.554709	0.660300	0.182006	0.042*
N17	0.5412 (5)	0.2427 (5)	0.3879 (5)	0.0377 (16)
H17A	0.476935	0.200461	0.387452	0.045*
H17B	0.575102	0.258503	0.331183	0.045*
N18	0.4246 (6)	0.6339 (8)	0.5819 (5)	0.053 (2)
H18A	0.460210	0.604207	0.583681	0.064*
H18B	0.419452	0.660561	0.525327	0.064*
N23	0.4760 (5)	0.4455 (5)	0.4975 (6)	0.0391 (16)
H23A	0.528221	0.505342	0.492391	0.047*
H23B	0.462851	0.412951	0.554881	0.047*
N14	0.6779 (6)	0.8008 (5)	0.6452 (6)	0.0453 (19)
H14A	0.704721	0.865610	0.650887	0.054*
H14B	0.642420	0.770062	0.591649	0.054*
N24	0.7449 (6)	0.7965 (5)	0.7989 (6)	0.0392 (17)
H24A	0.771463	0.861340	0.803855	0.047*
H24B	0.754017	0.763102	0.847274	0.047*
N27	0.5341 (5)	0.2577 (6)	0.5602 (5)	0.0423 (17)
H27A	0.469826	0.215253	0.557948	0.051*
H27B	0.562964	0.283297	0.618230	0.051*
N13	0.4360 (7)	0.4528 (5)	0.3301 (6)	0.055 (2)
H13A	0.488334	0.512651	0.325355	0.066*
H13B	0.397155	0.425693	0.277504	0.066*
C7	0.5878 (6)	0.2833 (6)	0.4753 (6)	0.0289 (15)
C5	0.5796 (5)	0.6262 (5)	0.0476 (6)	0.0235 (14)
C8	0.3775 (6)	0.6385 (6)	0.6667 (6)	0.0327 (17)
C4	0.6910 (6)	0.7489 (6)	0.7182 (6)	0.0287 (16)
N15	0.5308 (5)	0.5733 (6)	−0.0361 (5)	0.0390 (17)
H15A	0.465422	0.540652	−0.037556	0.047*
H15B	0.564615	0.571834	−0.088574	0.047*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0226 (4)	0.0229 (4)	0.0241 (4)	0.0130 (3)	−0.0008 (3)	−0.0001 (3)
Se2	0.0180 (3)	0.0262 (4)	0.0252 (4)	0.0105 (3)	0.0000 (3)	0.0026 (3)
Se3	0.0218 (4)	0.0181 (3)	0.0243 (4)	0.0090 (3)	0.0010 (3)	0.0004 (3)
Se4	0.0237 (4)	0.0192 (3)	0.0266 (5)	0.0091 (3)	0.0002 (3)	−0.0001 (3)
Se5	0.0188 (3)	0.0208 (3)	0.0264 (4)	0.0096 (3)	−0.0014 (3)	−0.0005 (3)
Se6	0.0209 (4)	0.0221 (4)	0.0257 (4)	0.0122 (3)	−0.0006 (3)	−0.0001 (3)
Se7	0.0206 (4)	0.0274 (4)	0.0300 (5)	0.0030 (3)	−0.0017 (3)	0.0008 (3)
Se8	0.0308 (4)	0.0250 (4)	0.0259 (5)	0.0180 (3)	−0.0021 (3)	−0.0010 (3)
Se9	0.0213 (4)	0.0379 (4)	0.0364 (5)	0.0156 (3)	0.0041 (3)	0.0095 (3)
C6	0.028 (3)	0.018 (3)	0.029 (4)	0.014 (3)	−0.005 (3)	−0.002 (3)
C2	0.022 (3)	0.035 (4)	0.024 (4)	0.017 (3)	−0.001 (3)	−0.004 (3)
C9	0.026 (3)	0.027 (4)	0.030 (4)	0.013 (3)	0.003 (3)	0.003 (3)
C3	0.029 (3)	0.024 (3)	0.023 (4)	0.010 (3)	0.004 (3)	−0.001 (3)
C1	0.030 (4)	0.024 (3)	0.022 (4)	0.013 (3)	0.000 (3)	0.000 (3)
N16	0.027 (3)	0.049 (4)	0.028 (3)	0.023 (3)	0.005 (3)	0.006 (3)
N21	0.028 (3)	0.054 (4)	0.031 (4)	0.023 (3)	−0.002 (3)	−0.005 (3)
N19	0.032 (3)	0.057 (4)	0.026 (4)	0.027 (3)	0.003 (3)	0.002 (3)
N29	0.030 (3)	0.066 (5)	0.030 (4)	0.020 (4)	−0.001 (3)	−0.013 (3)
N22	0.032 (4)	0.119 (8)	0.029 (4)	0.042 (5)	−0.011 (3)	−0.021 (4)
N26	0.037 (4)	0.075 (5)	0.030 (4)	0.041 (4)	0.001 (3)	0.006 (3)
N11	0.033 (3)	0.039 (3)	0.029 (4)	0.024 (3)	0.007 (3)	0.008 (3)
N12	0.058 (5)	0.066 (5)	0.025 (4)	0.051 (4)	0.003 (3)	0.005 (3)
N28	0.062 (5)	0.076 (6)	0.036 (4)	0.057 (5)	0.016 (4)	0.023 (4)
N25	0.026 (3)	0.040 (4)	0.032 (4)	0.011 (3)	0.007 (3)	−0.005 (3)
N17	0.023 (3)	0.038 (4)	0.036 (4)	0.004 (3)	0.004 (3)	−0.004 (3)
N18	0.070 (5)	0.103 (7)	0.025 (4)	0.072 (6)	0.019 (4)	0.025 (4)
N23	0.036 (4)	0.028 (3)	0.036 (4)	0.003 (3)	−0.003 (3)	−0.004 (3)
N14	0.071 (5)	0.026 (3)	0.036 (4)	0.022 (4)	−0.011 (4)	−0.002 (3)
N24	0.053 (4)	0.021 (3)	0.038 (4)	0.014 (3)	−0.005 (3)	0.001 (3)
N27	0.022 (3)	0.057 (4)	0.033 (4)	0.009 (3)	−0.003 (3)	−0.008 (3)
N13	0.074 (6)	0.024 (3)	0.033 (4)	0.000 (4)	−0.007 (4)	0.001 (3)
C7	0.027 (3)	0.030 (4)	0.032 (4)	0.016 (3)	−0.002 (3)	−0.005 (3)
C5	0.025 (3)	0.023 (3)	0.021 (3)	0.010 (3)	−0.002 (3)	0.001 (3)
C8	0.033 (4)	0.046 (4)	0.029 (4)	0.028 (4)	0.007 (3)	0.003 (3)
C4	0.032 (4)	0.030 (4)	0.022 (4)	0.014 (3)	0.008 (3)	0.004 (3)
N15	0.020 (3)	0.058 (4)	0.029 (4)	0.012 (3)	−0.001 (3)	−0.012 (3)

Geometric parameters (Å, º)

Se1—C1	1.876 (7)	N11—H11B	0.8600
Se2—C2	1.870 (7)	N12—H12A	0.8600
Se3—C3	1.880 (7)	N12—H12B	0.8600
Se4—C4	1.874 (8)	N28—H28A	0.8600
Se5—C5	1.859 (7)	N28—H28B	0.8600
Se6—C6	1.870 (7)	N28—C8	1.308 (11)
Se7—C7	1.879 (7)	N25—H25A	0.8600
Se8—C8	1.854 (7)	N25—H25B	0.8600
Se9—C9	1.872 (7)	N25—C5	1.328 (10)
C6—N16	1.311 (10)	N17—H17A	0.8600
C6—N26	1.327 (9)	N17—H17B	0.8600
C2—N21	1.317 (10)	N17—C7	1.315 (11)
C2—N22	1.299 (10)	N18—H18A	0.8600
C9—N19	1.314 (10)	N18—H18B	0.8600
C9—N29	1.301 (11)	N18—C8	1.334 (10)
C3—N23	1.327 (10)	N23—H23A	0.8600
C3—N13	1.300 (10)	N23—H23B	0.8600
C1—N11	1.312 (10)	N14—H14A	0.8600
C1—N12	1.329 (10)	N14—H14B	0.8600
N16—H16A	0.8600	N14—C4	1.309 (10)
N16—H16B	0.8600	N24—H24A	0.8600
N21—H21A	0.8600	N24—H24B	0.8600
N21—H21B	0.8600	N24—C4	1.302 (11)
N19—H19A	0.8600	N27—H27A	0.8600
N19—H19B	0.8600	N27—H27B	0.8600
N29—H29A	0.8600	N27—C7	1.308 (10)
N29—H29B	0.8600	N13—H13A	0.8600
N22—H22A	0.8600	N13—H13B	0.8600
N22—H22B	0.8600	C5—N15	1.333 (10)
N26—H26A	0.8600	N15—H15A	0.8600
N26—H26B	0.8600	N15—H15B	0.8600
N11—H11A	0.8600
N16—C6—Se6	120.7 (5)	C8—N28—H28B	120.0
N16—C6—N26	118.7 (6)	H25A—N25—H25B	120.0
N26—C6—Se6	120.6 (5)	C5—N25—H25A	120.0
N21—C2—Se2	120.7 (5)	C5—N25—H25B	120.0
N22—C2—Se2	119.2 (6)	H17A—N17—H17B	120.0
N22—C2—N21	120.1 (7)	C7—N17—H17A	120.0
N19—C9—Se9	120.3 (6)	C7—N17—H17B	120.0
N29—C9—Se9	120.5 (6)	H18A—N18—H18B	120.0
N29—C9—N19	119.2 (7)	C8—N18—H18A	120.0
N23—C3—Se3	119.8 (5)	C8—N18—H18B	120.0
N13—C3—Se3	120.4 (6)	C3—N23—H23A	120.0
N13—C3—N23	119.7 (7)	C3—N23—H23B	120.0
N11—C1—Se1	120.7 (5)	H23A—N23—H23B	120.0
N11—C1—N12	118.6 (7)	H14A—N14—H14B	120.0
N12—C1—Se1	120.7 (5)	C4—N14—H14A	120.0
C6—N16—H16A	120.0	C4—N14—H14B	120.0
C6—N16—H16B	120.0	H24A—N24—H24B	120.0
H16A—N16—H16B	120.0	C4—N24—H24A	120.0
C2—N21—H21A	120.0	C4—N24—H24B	120.0
C2—N21—H21B	120.0	H27A—N27—H27B	120.0
H21A—N21—H21B	120.0	C7—N27—H27A	120.0
C9—N19—H19A	120.0	C7—N27—H27B	120.0
C9—N19—H19B	120.0	C3—N13—H13A	120.0
H19A—N19—H19B	120.0	C3—N13—H13B	120.0
C9—N29—H29A	120.0	H13A—N13—H13B	120.0
C9—N29—H29B	120.0	N17—C7—Se7	120.0 (6)
H29A—N29—H29B	120.0	N27—C7—Se7	121.6 (6)
C2—N22—H22A	120.0	N27—C7—N17	118.4 (7)
C2—N22—H22B	120.0	N25—C5—Se5	121.9 (5)
H22A—N22—H22B	120.0	N25—C5—N15	118.3 (7)
C6—N26—H26A	120.0	N15—C5—Se5	119.8 (5)
C6—N26—H26B	120.0	N28—C8—Se8	121.9 (6)
H26A—N26—H26B	120.0	N28—C8—N18	117.5 (7)
C1—N11—H11A	120.0	N18—C8—Se8	120.6 (6)
C1—N11—H11B	120.0	N14—C4—Se4	120.2 (6)
H11A—N11—H11B	120.0	N24—C4—Se4	120.5 (6)
C1—N12—H12A	120.0	N24—C4—N14	119.3 (7)
C1—N12—H12B	120.0	C5—N15—H15A	120.0
H12A—N12—H12B	120.0	C5—N15—H15B	120.0
H28A—N28—H28B	120.0	H15A—N15—H15B	120.0
C8—N28—H28A	120.0

Selenourea (phase_alpha_Selenourea_210K)

Crystal data

CH4N2Se	Dx = 2.122 Mg m^−3
Mr = 123.02	Cu Kα radiation, λ = 1.54184 Å
Trigonal, P31	Cell parameters from 6757 reflections
a = 15.2065 (1) Å	θ = 3.4–72.3°
c = 12.9770 (1) Å	µ = 11.37 mm^−1
V = 2598.74 (4) Å^3	T = 210 K
Z = 27	Plate, orange
F(000) = 1566	0.25 × 0.10 × 0.05 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	3970 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	3937 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.037
Detector resolution: 10.5384 pixels mm^-1	θmax = 72.5°, θmin = 3.4°
ω scans	h = −16→18
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −18→18
Tmin = 0.399, Tmax = 1.000	l = −13→14
6773 measured reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0592P)^2 + 1.765P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.033	(Δ/σ)max < 0.001
wR(F^2) = 0.095	Δρmax = 0.59 e Å^−3
S = 1.13	Δρmin = −0.61 e Å^−3
3970 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
326 parameters	Extinction coefficient: 0.00075 (6)
1 restraint	Absolute structure: Refined as a perfect inversion twin.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.5
Hydrogen site location: inferred from neighbouring sites

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component perfect inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	0.30649 (6)	0.35131 (6)	0.09711 (6)	0.02522 (19)
Se2	0.39603 (6)	0.36002 (6)	0.75804 (6)	0.0261 (2)
Se3	0.30493 (6)	0.27021 (6)	0.42647 (6)	0.02469 (19)
Se4	0.63110 (6)	0.60739 (6)	0.70724 (6)	0.0269 (2)
Se5	0.72092 (6)	0.69408 (6)	0.05120 (6)	0.0248 (2)
Se6	0.63338 (6)	0.70210 (6)	0.38322 (6)	0.02499 (19)
Se7	0.72815 (6)	0.37680 (7)	0.47558 (7)	0.0338 (2)
Se8	0.29835 (6)	0.70003 (6)	0.66373 (7)	0.0286 (2)
Se9	1.06965 (6)	1.02694 (7)	0.45769 (9)	0.0351 (2)
C6	0.7498 (5)	0.6899 (5)	0.3919 (6)	0.0264 (14)
C2	0.2581 (6)	0.3201 (6)	0.7556 (6)	0.0293 (17)
C9	0.9336 (6)	0.9957 (6)	0.4523 (7)	0.0318 (17)
C3	0.4151 (6)	0.4032 (6)	0.4169 (6)	0.0318 (17)
C1	0.3866 (6)	0.2897 (6)	0.0947 (6)	0.0272 (16)
N16	0.8047 (5)	0.7017 (6)	0.3092 (5)	0.0364 (16)
H16A	0.857924	0.695804	0.313430	0.044*
H16B	0.787241	0.715219	0.250873	0.044*
N21	0.2105 (5)	0.3180 (6)	0.8412 (6)	0.0414 (17)
H21A	0.147639	0.301711	0.839136	0.050*
H21B	0.242291	0.332854	0.899050	0.050*
N19	0.8901 (5)	1.0068 (6)	0.5350 (6)	0.0394 (17)
H19A	0.828029	0.993381	0.532352	0.047*
H19B	0.923606	1.027626	0.591649	0.047*
N29	0.8821 (6)	0.9644 (7)	0.3680 (6)	0.050 (2)
H29A	0.820097	0.951193	0.366332	0.060*
H29B	0.909697	0.956799	0.313430	0.060*
N22	0.2099 (6)	0.2976 (9)	0.6691 (7)	0.067 (3)
H22A	0.147012	0.281408	0.667571	0.081*
H22B	0.240590	0.298841	0.613037	0.081*
N26	0.7779 (6)	0.6692 (7)	0.4806 (6)	0.047 (2)
H26A	0.831342	0.663530	0.483720	0.057*
H26B	0.742741	0.661328	0.535271	0.057*
N11	0.4368 (5)	0.2922 (6)	0.0113 (5)	0.0339 (15)
H11A	0.472951	0.263139	0.011042	0.041*
H11B	0.433596	0.322901	−0.042953	0.041*
N12	0.3932 (7)	0.2416 (6)	0.1771 (5)	0.0434 (19)
H12A	0.429829	0.213103	0.175054	0.052*
H12B	0.360997	0.239016	0.232489	0.052*
N28	0.3876 (7)	0.5966 (8)	0.7508 (7)	0.054 (2)
H28A	0.423629	0.567487	0.750283	0.065*
H28B	0.357981	0.598340	0.806582	0.065*
N25	0.5253 (5)	0.6264 (6)	0.1272 (6)	0.0394 (17)
H25A	0.460098	0.593262	0.124155	0.047*
H25B	0.555349	0.659862	0.181927	0.047*
N17	0.5409 (5)	0.2422 (6)	0.3878 (6)	0.0434 (19)
H17A	0.476570	0.200283	0.387672	0.052*
H17B	0.574439	0.257371	0.330927	0.052*
N18	0.4246 (7)	0.6337 (9)	0.5825 (6)	0.060 (3)
H18A	0.460155	0.604083	0.584344	0.072*
H18B	0.419514	0.660414	0.525977	0.072*
N23	0.4751 (6)	0.4460 (5)	0.4971 (6)	0.0433 (17)
H23A	0.526911	0.506019	0.491735	0.052*
H23B	0.462334	0.413814	0.554596	0.052*
N14	0.6776 (7)	0.8005 (6)	0.6451 (6)	0.052 (2)
H14A	0.704194	0.865180	0.650977	0.063*
H14B	0.642375	0.769878	0.591425	0.063*
N24	0.7445 (6)	0.7963 (5)	0.7990 (6)	0.0436 (19)
H24A	0.770719	0.861066	0.803961	0.052*
H24B	0.753647	0.763031	0.847280	0.052*
N27	0.5340 (6)	0.2581 (7)	0.5601 (6)	0.049 (2)
H27A	0.469812	0.215916	0.557531	0.059*
H27B	0.562654	0.283577	0.618187	0.059*
N13	0.4352 (7)	0.4527 (6)	0.3303 (6)	0.059 (3)
H13A	0.487177	0.512712	0.325590	0.071*
H13B	0.396518	0.425422	0.277698	0.071*
C7	0.5883 (6)	0.2834 (6)	0.4754 (7)	0.0339 (17)
C5	0.5797 (6)	0.6259 (6)	0.0473 (6)	0.0259 (15)
C8	0.3777 (7)	0.6382 (7)	0.6666 (7)	0.0367 (19)
C4	0.6907 (6)	0.7486 (6)	0.7179 (6)	0.0316 (17)
N15	0.5311 (5)	0.5735 (6)	−0.0363 (6)	0.0443 (19)
H15A	0.465800	0.540806	−0.037777	0.053*
H15B	0.564918	0.572178	−0.088806	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0252 (4)	0.0251 (4)	0.0278 (4)	0.0145 (3)	−0.0007 (3)	0.0002 (3)
Se2	0.0202 (4)	0.0289 (4)	0.0286 (5)	0.0118 (3)	0.0002 (3)	0.0026 (3)
Se3	0.0242 (4)	0.0200 (4)	0.0282 (4)	0.0097 (3)	0.0009 (3)	0.0006 (3)
Se4	0.0264 (4)	0.0212 (4)	0.0305 (5)	0.0099 (3)	0.0002 (3)	−0.0002 (3)
Se5	0.0211 (4)	0.0230 (4)	0.0298 (4)	0.0107 (3)	−0.0014 (3)	−0.0006 (3)
Se6	0.0229 (4)	0.0247 (4)	0.0295 (4)	0.0135 (3)	−0.0007 (3)	0.0001 (3)
Se7	0.0229 (4)	0.0303 (4)	0.0349 (5)	0.0033 (3)	−0.0019 (3)	0.0008 (4)
Se8	0.0342 (5)	0.0278 (4)	0.0297 (5)	0.0199 (4)	−0.0023 (3)	−0.0011 (3)
Se9	0.0235 (4)	0.0414 (5)	0.0413 (5)	0.0170 (4)	0.0044 (3)	0.0098 (4)
C6	0.027 (3)	0.025 (3)	0.031 (4)	0.015 (3)	−0.004 (3)	−0.001 (3)
C2	0.025 (4)	0.037 (4)	0.030 (4)	0.018 (3)	−0.001 (3)	−0.005 (3)
C9	0.028 (4)	0.029 (4)	0.037 (5)	0.014 (3)	0.003 (3)	0.003 (3)
C3	0.032 (4)	0.028 (4)	0.030 (4)	0.011 (3)	0.005 (3)	−0.002 (3)
C1	0.029 (4)	0.026 (4)	0.025 (4)	0.013 (3)	0.000 (3)	0.001 (3)
N16	0.033 (3)	0.050 (4)	0.033 (4)	0.026 (3)	0.007 (3)	0.006 (3)
N21	0.032 (4)	0.059 (5)	0.036 (4)	0.025 (4)	0.001 (3)	−0.002 (4)
N19	0.033 (3)	0.061 (5)	0.032 (4)	0.029 (3)	0.005 (3)	0.004 (3)
N29	0.032 (4)	0.081 (6)	0.033 (4)	0.025 (4)	−0.004 (3)	−0.017 (4)
N22	0.037 (4)	0.143 (10)	0.034 (5)	0.054 (6)	−0.012 (4)	−0.022 (5)
N26	0.043 (4)	0.083 (6)	0.034 (4)	0.046 (4)	0.000 (3)	0.006 (4)
N11	0.033 (3)	0.047 (4)	0.032 (4)	0.029 (3)	0.007 (3)	0.008 (3)
N12	0.063 (5)	0.069 (5)	0.027 (4)	0.054 (5)	0.005 (3)	0.007 (3)
N28	0.074 (6)	0.082 (6)	0.041 (5)	0.066 (6)	0.019 (4)	0.026 (4)
N25	0.029 (3)	0.047 (4)	0.036 (4)	0.014 (3)	0.006 (3)	−0.007 (3)
N17	0.028 (3)	0.045 (4)	0.041 (5)	0.006 (3)	0.004 (3)	−0.006 (3)
N18	0.074 (6)	0.119 (8)	0.031 (4)	0.081 (7)	0.018 (4)	0.024 (5)
N23	0.043 (4)	0.033 (4)	0.039 (4)	0.007 (3)	−0.003 (3)	−0.004 (3)
N14	0.084 (6)	0.028 (4)	0.041 (4)	0.025 (4)	−0.014 (4)	−0.002 (3)
N24	0.059 (5)	0.022 (3)	0.042 (5)	0.015 (3)	−0.008 (4)	0.000 (3)
N27	0.027 (4)	0.066 (5)	0.039 (5)	0.011 (4)	−0.002 (3)	−0.007 (4)
N13	0.077 (6)	0.028 (4)	0.036 (4)	−0.001 (4)	−0.007 (4)	0.003 (3)
C7	0.026 (4)	0.033 (4)	0.039 (5)	0.013 (3)	−0.004 (3)	−0.006 (4)
C5	0.027 (4)	0.026 (4)	0.023 (4)	0.012 (3)	−0.001 (3)	0.001 (3)
C8	0.040 (5)	0.051 (5)	0.032 (5)	0.033 (4)	0.007 (4)	0.006 (4)
C4	0.038 (4)	0.031 (4)	0.025 (4)	0.016 (3)	0.006 (3)	0.000 (3)
N15	0.024 (3)	0.062 (5)	0.031 (4)	0.010 (3)	−0.001 (3)	−0.011 (3)

Geometric parameters (Å, º)

Se1—C1	1.872 (8)	N11—H11B	0.8600
Se2—C2	1.869 (7)	N12—H12A	0.8600
Se3—C3	1.878 (8)	N12—H12B	0.8600
Se4—C4	1.872 (8)	N28—H28A	0.8600
Se5—C5	1.860 (8)	N28—H28B	0.8600
Se6—C6	1.873 (7)	N28—C8	1.309 (11)
Se7—C7	1.876 (8)	N25—H25A	0.8600
Se8—C8	1.864 (8)	N25—H25B	0.8600
Se9—C9	1.878 (8)	N25—C5	1.329 (10)
C6—N16	1.315 (10)	N17—H17A	0.8600
C6—N26	1.320 (10)	N17—H17B	0.8600
C2—N21	1.317 (11)	N17—C7	1.324 (12)
C2—N22	1.290 (11)	N18—H18A	0.8600
C9—N19	1.316 (11)	N18—H18B	0.8600
C9—N29	1.291 (12)	N18—C8	1.324 (11)
C3—N23	1.321 (11)	N23—H23A	0.8600
C3—N13	1.301 (11)	N23—H23B	0.8600
C1—N11	1.314 (10)	N14—H14A	0.8600
C1—N12	1.327 (10)	N14—H14B	0.8600
N16—H16A	0.8600	N14—C4	1.309 (11)
N16—H16B	0.8600	N24—H24A	0.8600
N21—H21A	0.8600	N24—H24B	0.8600
N21—H21B	0.8600	N24—C4	1.307 (11)
N19—H19A	0.8600	N27—H27A	0.8600
N19—H19B	0.8600	N27—H27B	0.8600
N29—H29A	0.8600	N27—C7	1.311 (12)
N29—H29B	0.8600	N13—H13A	0.8600
N22—H22A	0.8600	N13—H13B	0.8600
N22—H22B	0.8600	C5—N15	1.330 (11)
N26—H26A	0.8600	N15—H15A	0.8600
N26—H26B	0.8600	N15—H15B	0.8600
N11—H11A	0.8600
N16—C6—Se6	120.3 (6)	C8—N28—H28B	120.0
N16—C6—N26	119.0 (7)	H25A—N25—H25B	120.0
N26—C6—Se6	120.7 (6)	C5—N25—H25A	120.0
N21—C2—Se2	120.5 (6)	C5—N25—H25B	120.0
N22—C2—Se2	119.8 (6)	H17A—N17—H17B	120.0
N22—C2—N21	119.6 (7)	C7—N17—H17A	120.0
N19—C9—Se9	119.9 (6)	C7—N17—H17B	120.0
N29—C9—Se9	120.9 (6)	H18A—N18—H18B	120.0
N29—C9—N19	119.1 (8)	C8—N18—H18A	120.0
N23—C3—Se3	120.2 (6)	C8—N18—H18B	120.0
N13—C3—Se3	120.3 (6)	C3—N23—H23A	120.0
N13—C3—N23	119.4 (7)	C3—N23—H23B	120.0
N11—C1—Se1	120.9 (6)	H23A—N23—H23B	120.0
N11—C1—N12	118.4 (7)	H14A—N14—H14B	120.0
N12—C1—Se1	120.7 (6)	C4—N14—H14A	120.0
C6—N16—H16A	120.0	C4—N14—H14B	120.0
C6—N16—H16B	120.0	H24A—N24—H24B	120.0
H16A—N16—H16B	120.0	C4—N24—H24A	120.0
C2—N21—H21A	120.0	C4—N24—H24B	120.0
C2—N21—H21B	120.0	H27A—N27—H27B	120.0
H21A—N21—H21B	120.0	C7—N27—H27A	120.0
C9—N19—H19A	120.0	C7—N27—H27B	120.0
C9—N19—H19B	120.0	C3—N13—H13A	120.0
H19A—N19—H19B	120.0	C3—N13—H13B	120.0
C9—N29—H29A	120.0	H13A—N13—H13B	120.0
C9—N29—H29B	120.0	N17—C7—Se7	120.1 (6)
H29A—N29—H29B	120.0	N27—C7—Se7	122.0 (6)
C2—N22—H22A	120.0	N27—C7—N17	117.8 (8)
C2—N22—H22B	120.0	N25—C5—Se5	121.6 (6)
H22A—N22—H22B	120.0	N25—C5—N15	118.6 (7)
C6—N26—H26A	120.0	N15—C5—Se5	119.8 (6)
C6—N26—H26B	120.0	N28—C8—Se8	121.3 (6)
H26A—N26—H26B	120.0	N28—C8—N18	117.9 (8)
C1—N11—H11A	120.0	N18—C8—Se8	120.7 (6)
C1—N11—H11B	120.0	N14—C4—Se4	120.4 (7)
H11A—N11—H11B	120.0	N24—C4—Se4	120.4 (6)
C1—N12—H12A	120.0	N24—C4—N14	119.2 (8)
C1—N12—H12B	120.0	C5—N15—H15A	120.0
H12A—N12—H12B	120.0	C5—N15—H15B	120.0
H28A—N28—H28B	120.0	H15A—N15—H15B	120.0
C8—N28—H28A	120.0

Selenourea (phase_alpha_Selenourea_230K)

Crystal data

CH4N2Se	Dx = 2.116 Mg m^−3
Mr = 123.02	Cu Kα radiation, λ = 1.54184 Å
Trigonal, P31	Cell parameters from 6730 reflections
a = 15.2222 (1) Å	θ = 3.3–72.2°
c = 12.9882 (1) Å	µ = 11.33 mm^−1
V = 2606.36 (4) Å^3	T = 230 K
Z = 27	Plate, orange
F(000) = 1566	0.25 × 0.10 × 0.05 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	3976 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	3955 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.031
Detector resolution: 10.5384 pixels mm^-1	θmax = 72.3°, θmin = 3.4°
ω scans	h = −18→16
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −18→18
Tmin = 0.166, Tmax = 1.000	l = −14→13
6843 measured reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.060P)^2 + 1.262P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.033	(Δ/σ)max = 0.001
wR(F^2) = 0.090	Δρmax = 0.89 e Å^−3
S = 1.09	Δρmin = −0.68 e Å^−3
3976 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
326 parameters	Extinction coefficient: 0.00065 (5)
1 restraint	Absolute structure: Classical Flack method preferred over Parsons because s.u. lower.
Primary atom site location: dual	Absolute structure parameter: 0.00 (4)
Hydrogen site location: inferred from neighbouring sites

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	0.30642 (5)	0.35126 (6)	0.09714 (5)	0.02672 (18)
Se2	0.39569 (6)	0.36011 (6)	0.75796 (5)	0.02792 (19)
Se3	0.30497 (6)	0.27042 (5)	0.42647 (6)	0.02614 (18)
Se4	0.63106 (6)	0.60742 (6)	0.70725 (5)	0.0288 (2)
Se5	0.72097 (5)	0.69394 (5)	0.05110 (6)	0.02652 (19)
Se6	0.63343 (6)	0.70204 (6)	0.38315 (5)	0.02647 (18)
Se7	0.72825 (6)	0.37668 (7)	0.47495 (7)	0.0363 (2)
Se8	0.29832 (6)	0.70011 (5)	0.66405 (7)	0.0307 (2)
Se9	1.06981 (6)	1.02755 (7)	0.45860 (8)	0.0371 (2)
C6	0.7494 (5)	0.6896 (5)	0.3910 (5)	0.0279 (13)
C2	0.2576 (6)	0.3195 (6)	0.7551 (6)	0.0334 (16)
C9	0.9341 (6)	0.9960 (6)	0.4527 (6)	0.0336 (16)
C3	0.4149 (5)	0.4029 (5)	0.4161 (6)	0.0342 (16)
C1	0.3869 (6)	0.2899 (6)	0.0942 (5)	0.0291 (15)
N16	0.8049 (5)	0.7010 (5)	0.3094 (5)	0.0390 (14)
H16A	0.857435	0.694155	0.314355	0.047*
H16B	0.788666	0.715435	0.250914	0.047*
N21	0.2100 (5)	0.3168 (6)	0.8405 (5)	0.0439 (16)
H21A	0.146982	0.299954	0.838597	0.053*
H21B	0.241770	0.331910	0.898342	0.053*
N19	0.8894 (5)	1.0072 (6)	0.5360 (6)	0.0475 (17)
H19A	0.827482	0.993828	0.532804	0.057*
H19B	0.922506	1.027922	0.592833	0.057*
N29	0.8824 (6)	0.9647 (7)	0.3682 (6)	0.056 (2)
H29A	0.820548	0.951721	0.366614	0.067*
H29B	0.909894	0.957006	0.313716	0.067*
N22	0.2092 (6)	0.2967 (9)	0.6689 (6)	0.072 (3)
H22A	0.146201	0.279882	0.667627	0.086*
H22B	0.239814	0.298209	0.612755	0.086*
N26	0.7768 (6)	0.6675 (6)	0.4798 (5)	0.0483 (18)
H26A	0.829671	0.660956	0.482778	0.058*
H26B	0.741620	0.659585	0.534417	0.058*
N11	0.4364 (5)	0.2917 (5)	0.0105 (5)	0.0363 (14)
H11A	0.471905	0.262063	0.009926	0.044*
H11B	0.433242	0.322524	−0.043624	0.044*
N12	0.3931 (6)	0.2419 (6)	0.1764 (5)	0.0479 (18)
H12A	0.428923	0.212707	0.174463	0.058*
H12B	0.361182	0.240013	0.231774	0.058*
N28	0.3870 (7)	0.5968 (7)	0.7511 (6)	0.056 (2)
H28A	0.422676	0.567362	0.751223	0.068*
H28B	0.357376	0.599141	0.806524	0.068*
N25	0.5259 (5)	0.6263 (6)	0.1268 (6)	0.0443 (16)
H25A	0.460722	0.593467	0.124264	0.053*
H25B	0.556372	0.659586	0.181430	0.053*
N17	0.5419 (5)	0.2427 (6)	0.3870 (6)	0.0470 (18)
H17A	0.477571	0.201248	0.386549	0.056*
H17B	0.575798	0.257628	0.330508	0.056*
N18	0.4242 (7)	0.6335 (8)	0.5826 (6)	0.063 (3)
H18A	0.459315	0.603444	0.585216	0.076*
H18B	0.419632	0.659915	0.525789	0.076*
N23	0.4746 (5)	0.4457 (5)	0.4969 (5)	0.0452 (16)
H23A	0.525621	0.506235	0.492210	0.054*
H23B	0.462260	0.413033	0.554002	0.054*
N14	0.6778 (7)	0.8003 (5)	0.6439 (6)	0.058 (2)
H14A	0.704618	0.864986	0.649435	0.070*
H14B	0.642917	0.769616	0.590164	0.070*
N24	0.7429 (6)	0.7956 (5)	0.7986 (6)	0.0489 (19)
H24A	0.769419	0.860270	0.803454	0.059*
H24B	0.751265	0.762156	0.847316	0.059*
N27	0.5347 (5)	0.2588 (7)	0.5590 (6)	0.057 (2)
H27A	0.470464	0.217194	0.556515	0.068*
H27B	0.563508	0.284301	0.616949	0.068*
N13	0.4345 (7)	0.4531 (5)	0.3308 (6)	0.063 (2)
H13A	0.485672	0.513525	0.326916	0.075*
H13B	0.396228	0.425985	0.277998	0.075*
C7	0.5887 (6)	0.2833 (6)	0.4746 (6)	0.0352 (16)
C5	0.5800 (5)	0.6257 (5)	0.0458 (5)	0.0275 (14)
C8	0.3777 (6)	0.6388 (6)	0.6651 (6)	0.0358 (16)
C4	0.6900 (6)	0.7482 (6)	0.7178 (6)	0.0342 (16)
N15	0.5307 (5)	0.5739 (6)	−0.0365 (5)	0.0499 (19)
H15A	0.465456	0.541600	−0.037224	0.060*
H15B	0.563753	0.572297	−0.089485	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0285 (4)	0.0287 (4)	0.0258 (4)	0.0164 (3)	−0.0006 (3)	−0.0001 (3)
Se2	0.0235 (3)	0.0325 (4)	0.0272 (4)	0.0136 (3)	0.0000 (3)	0.0026 (3)
Se3	0.0276 (4)	0.0231 (3)	0.0260 (4)	0.0114 (3)	0.0007 (3)	0.0008 (3)
Se4	0.0302 (4)	0.0242 (3)	0.0289 (5)	0.0113 (3)	0.0001 (3)	0.0001 (3)
Se5	0.0242 (3)	0.0269 (3)	0.0280 (4)	0.0125 (3)	−0.0015 (3)	−0.0006 (3)
Se6	0.0265 (4)	0.0283 (4)	0.0269 (4)	0.0155 (3)	−0.0004 (3)	0.0000 (3)
Se7	0.0264 (4)	0.0343 (4)	0.0340 (5)	0.0044 (3)	−0.0020 (3)	0.0008 (3)
Se8	0.0385 (4)	0.0315 (4)	0.0283 (5)	0.0223 (3)	−0.0024 (3)	−0.0013 (3)
Se9	0.0271 (4)	0.0459 (5)	0.0392 (5)	0.0190 (4)	0.0045 (3)	0.0103 (4)
C6	0.026 (3)	0.029 (3)	0.032 (4)	0.016 (3)	−0.002 (3)	−0.004 (3)
C2	0.033 (4)	0.046 (4)	0.028 (4)	0.025 (3)	0.000 (3)	−0.003 (3)
C9	0.033 (3)	0.032 (4)	0.036 (4)	0.018 (3)	0.007 (3)	0.003 (3)
C3	0.035 (4)	0.032 (4)	0.029 (4)	0.012 (3)	0.003 (3)	−0.007 (3)
C1	0.035 (4)	0.032 (4)	0.023 (4)	0.018 (3)	0.001 (3)	0.002 (3)
N16	0.038 (3)	0.051 (4)	0.034 (4)	0.027 (3)	0.005 (3)	0.003 (3)
N21	0.036 (3)	0.070 (5)	0.032 (4)	0.031 (3)	0.003 (3)	−0.002 (3)
N19	0.038 (3)	0.076 (5)	0.039 (4)	0.037 (4)	0.002 (3)	0.001 (3)
N29	0.035 (4)	0.092 (6)	0.039 (4)	0.029 (4)	−0.003 (3)	−0.012 (4)
N22	0.040 (4)	0.154 (10)	0.033 (4)	0.057 (5)	−0.006 (3)	−0.012 (5)
N26	0.049 (4)	0.086 (6)	0.033 (4)	0.051 (4)	0.001 (3)	0.005 (3)
N11	0.039 (3)	0.049 (4)	0.031 (4)	0.030 (3)	0.006 (3)	0.004 (3)
N12	0.066 (5)	0.074 (5)	0.030 (4)	0.055 (4)	0.005 (3)	0.008 (3)
N28	0.077 (5)	0.084 (6)	0.041 (4)	0.065 (5)	0.020 (4)	0.022 (4)
N25	0.034 (3)	0.052 (4)	0.041 (4)	0.017 (3)	0.002 (3)	−0.011 (3)
N17	0.029 (3)	0.055 (4)	0.037 (4)	0.007 (3)	−0.001 (3)	−0.007 (3)
N18	0.080 (6)	0.120 (8)	0.031 (4)	0.081 (6)	0.015 (4)	0.021 (4)
N23	0.043 (4)	0.035 (3)	0.039 (4)	0.006 (3)	−0.001 (3)	0.001 (3)
N14	0.095 (6)	0.032 (3)	0.046 (4)	0.030 (4)	−0.015 (4)	0.001 (3)
N24	0.068 (5)	0.028 (3)	0.042 (4)	0.017 (3)	−0.011 (4)	0.000 (3)
N27	0.031 (3)	0.081 (6)	0.043 (4)	0.016 (4)	−0.002 (3)	−0.007 (4)
N13	0.084 (6)	0.027 (3)	0.038 (4)	−0.003 (4)	−0.003 (4)	0.005 (3)
C7	0.028 (3)	0.036 (4)	0.038 (4)	0.013 (3)	−0.006 (3)	−0.007 (3)
C5	0.030 (3)	0.030 (3)	0.021 (3)	0.014 (3)	0.000 (3)	0.004 (3)
C8	0.041 (4)	0.055 (5)	0.023 (4)	0.033 (4)	0.003 (3)	0.001 (3)
C4	0.043 (4)	0.031 (4)	0.027 (4)	0.018 (3)	0.008 (3)	0.003 (3)
N15	0.027 (3)	0.072 (5)	0.034 (4)	0.013 (3)	−0.004 (3)	−0.013 (3)

Geometric parameters (Å, º)

Se1—C1	1.877 (7)	N11—H11B	0.8600
Se2—C2	1.871 (7)	N12—H12A	0.8600
Se3—C3	1.874 (7)	N12—H12B	0.8600
Se4—C4	1.869 (7)	N28—H28A	0.8600
Se5—C5	1.860 (7)	N28—H28B	0.8600
Se6—C6	1.869 (6)	N28—C8	1.329 (11)
Se7—C7	1.875 (7)	N25—H25A	0.8600
Se8—C8	1.859 (7)	N25—H25B	0.8600
Se9—C9	1.873 (7)	N25—C5	1.339 (10)
C6—N16	1.312 (10)	N17—H17A	0.8600
C6—N26	1.326 (10)	N17—H17B	0.8600
C2—N21	1.315 (10)	N17—C7	1.319 (11)
C2—N22	1.289 (11)	N18—H18A	0.8600
C9—N19	1.334 (10)	N18—H18B	0.8600
C9—N29	1.295 (11)	N18—C8	1.309 (10)
C3—N23	1.326 (10)	N23—H23A	0.8600
C3—N13	1.293 (11)	N23—H23B	0.8600
C1—N11	1.314 (10)	N14—H14A	0.8600
C1—N12	1.323 (10)	N14—H14B	0.8600
N16—H16A	0.8600	N14—C4	1.316 (11)
N16—H16B	0.8600	N24—H24A	0.8600
N21—H21A	0.8600	N24—H24B	0.8600
N21—H21B	0.8600	N24—C4	1.300 (11)
N19—H19A	0.8600	N27—H27A	0.8600
N19—H19B	0.8600	N27—H27B	0.8600
N29—H29A	0.8600	N27—C7	1.307 (11)
N29—H29B	0.8600	N13—H13A	0.8600
N22—H22A	0.8600	N13—H13B	0.8600
N22—H22B	0.8600	C5—N15	1.318 (10)
N26—H26A	0.8600	N15—H15A	0.8600
N26—H26B	0.8600	N15—H15B	0.8600
N11—H11A	0.8600
N16—C6—Se6	121.4 (5)	C8—N28—H28B	120.0
N16—C6—N26	118.2 (6)	H25A—N25—H25B	120.0
N26—C6—Se6	120.4 (5)	C5—N25—H25A	120.0
N21—C2—Se2	120.3 (6)	C5—N25—H25B	120.0
N22—C2—Se2	120.2 (6)	H17A—N17—H17B	120.0
N22—C2—N21	119.5 (7)	C7—N17—H17A	120.0
N19—C9—Se9	120.1 (6)	C7—N17—H17B	120.0
N29—C9—Se9	121.2 (6)	H18A—N18—H18B	120.0
N29—C9—N19	118.6 (7)	C8—N18—H18A	120.0
N23—C3—Se3	119.7 (6)	C8—N18—H18B	120.0
N13—C3—Se3	121.0 (6)	C3—N23—H23A	120.0
N13—C3—N23	119.3 (7)	C3—N23—H23B	120.0
N11—C1—Se1	121.1 (5)	H23A—N23—H23B	120.0
N11—C1—N12	118.8 (7)	H14A—N14—H14B	120.0
N12—C1—Se1	120.1 (5)	C4—N14—H14A	120.0
C6—N16—H16A	120.0	C4—N14—H14B	120.0
C6—N16—H16B	120.0	H24A—N24—H24B	120.0
H16A—N16—H16B	120.0	C4—N24—H24A	120.0
C2—N21—H21A	120.0	C4—N24—H24B	120.0
C2—N21—H21B	120.0	H27A—N27—H27B	120.0
H21A—N21—H21B	120.0	C7—N27—H27A	120.0
C9—N19—H19A	120.0	C7—N27—H27B	120.0
C9—N19—H19B	120.0	C3—N13—H13A	120.0
H19A—N19—H19B	120.0	C3—N13—H13B	120.0
C9—N29—H29A	120.0	H13A—N13—H13B	120.0
C9—N29—H29B	120.0	N17—C7—Se7	119.9 (6)
H29A—N29—H29B	120.0	N27—C7—Se7	121.7 (6)
C2—N22—H22A	120.0	N27—C7—N17	118.3 (7)
C2—N22—H22B	120.0	N25—C5—Se5	120.6 (5)
H22A—N22—H22B	120.0	N15—C5—Se5	121.1 (5)
C6—N26—H26A	120.0	N15—C5—N25	118.3 (7)
C6—N26—H26B	120.0	N28—C8—Se8	120.0 (5)
H26A—N26—H26B	120.0	N18—C8—Se8	122.2 (6)
C1—N11—H11A	120.0	N18—C8—N28	117.8 (7)
C1—N11—H11B	120.0	N14—C4—Se4	120.4 (6)
H11A—N11—H11B	120.0	N24—C4—Se4	120.3 (6)
C1—N12—H12A	120.0	N24—C4—N14	119.3 (7)
C1—N12—H12B	120.0	C5—N15—H15A	120.0
H12A—N12—H12B	120.0	C5—N15—H15B	120.0
H28A—N28—H28B	120.0	H15A—N15—H15B	120.0
C8—N28—H28A	120.0

Selenourea (phase_alpha_Selenourea_250K)

Crystal data

CH4N2Se	Dx = 2.110 Mg m^−3
Mr = 123.02	Cu Kα radiation, λ = 1.54184 Å
Trigonal, P31	Cell parameters from 6687 reflections
a = 15.23887 (11) Å	θ = 3.3–72.2°
c = 12.99870 (13) Å	µ = 11.30 mm^−1
V = 2614.18 (5) Å^3	T = 250 K
Z = 27	Plate, orange
F(000) = 1566	0.25 × 0.10 × 0.05 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	4004 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	3972 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.037
Detector resolution: 10.5384 pixels mm^-1	θmax = 72.4°, θmin = 3.4°
ω scans	h = −18→18
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −18→16
Tmin = 0.195, Tmax = 1.000	l = −14→13
6882 measured reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0593P)^2 + 0.467P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.033	(Δ/σ)max = 0.001
wR(F^2) = 0.090	Δρmax = 0.67 e Å^−3
S = 1.09	Δρmin = −0.48 e Å^−3
4004 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
326 parameters	Extinction coefficient: 0.00076 (6)
1 restraint	Absolute structure: Refined as a perfect inversion twin.
Primary atom site location: dual	Absolute structure parameter: 0.5
Hydrogen site location: inferred from neighbouring sites

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component perfect inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	0.30629 (5)	0.35125 (6)	0.09713 (5)	0.03035 (18)
Se2	0.39526 (6)	0.36009 (6)	0.75806 (5)	0.03164 (19)
Se3	0.30491 (5)	0.27051 (5)	0.42653 (6)	0.02982 (18)
Se4	0.63098 (6)	0.60738 (6)	0.70713 (5)	0.0323 (2)
Se5	0.72097 (5)	0.69372 (5)	0.05091 (6)	0.02999 (18)
Se6	0.63358 (5)	0.70197 (6)	0.38306 (5)	0.03010 (18)
Se7	0.72844 (6)	0.37656 (7)	0.47447 (7)	0.0407 (2)
Se8	0.29825 (6)	0.70002 (5)	0.66411 (7)	0.0346 (2)
Se9	1.06983 (6)	1.02797 (7)	0.45938 (8)	0.0415 (2)
C6	0.7490 (5)	0.6889 (5)	0.3919 (6)	0.0325 (13)
C2	0.2570 (5)	0.3180 (6)	0.7562 (6)	0.0370 (16)
C9	0.9343 (6)	0.9964 (6)	0.4541 (6)	0.0381 (16)
C3	0.4141 (6)	0.4037 (5)	0.4176 (6)	0.0379 (16)
C1	0.3858 (6)	0.2897 (6)	0.0944 (5)	0.0336 (15)
N16	0.8041 (5)	0.7002 (5)	0.3094 (5)	0.0443 (15)
H16A	0.856760	0.693489	0.313885	0.053*
H16B	0.787319	0.714142	0.251058	0.053*
N21	0.2099 (5)	0.3164 (6)	0.8408 (5)	0.0490 (17)
H21A	0.146991	0.299554	0.838774	0.059*
H21B	0.241819	0.332264	0.898485	0.059*
N19	0.8901 (5)	1.0070 (6)	0.5355 (5)	0.0495 (17)
H19A	0.828093	0.993163	0.532221	0.059*
H19B	0.923021	1.027874	0.592382	0.059*
N29	0.8826 (6)	0.9647 (7)	0.3693 (6)	0.061 (2)
H29A	0.820709	0.951277	0.367588	0.073*
H29B	0.910375	0.957252	0.314969	0.073*
N22	0.2081 (6)	0.2940 (9)	0.6699 (6)	0.082 (3)
H22A	0.145196	0.277204	0.668538	0.099*
H22B	0.238520	0.294812	0.613821	0.099*
N26	0.7764 (6)	0.6675 (7)	0.4802 (6)	0.058 (2)
H26A	0.829290	0.661135	0.483374	0.069*
H26B	0.741363	0.659974	0.534799	0.069*
N11	0.4358 (5)	0.2920 (5)	0.0112 (5)	0.0407 (14)
H11A	0.471998	0.263264	0.010948	0.049*
H11B	0.432229	0.322362	−0.043160	0.049*
N12	0.3931 (6)	0.2422 (6)	0.1766 (5)	0.0538 (19)
H12A	0.429848	0.214010	0.174435	0.065*
H12B	0.361094	0.239619	0.231998	0.065*
N28	0.3865 (7)	0.5964 (7)	0.7512 (6)	0.065 (2)
H28A	0.422007	0.566780	0.750549	0.078*
H28B	0.357014	0.598113	0.806921	0.078*
N25	0.5264 (5)	0.6265 (6)	0.1267 (6)	0.0491 (17)
H25A	0.461283	0.593913	0.123814	0.059*
H25B	0.556647	0.659607	0.181359	0.059*
N17	0.5412 (5)	0.2423 (6)	0.3865 (6)	0.0548 (19)
H17A	0.476957	0.200558	0.386809	0.066*
H17B	0.574424	0.256810	0.329697	0.066*
N18	0.4244 (7)	0.6343 (8)	0.5834 (6)	0.074 (3)
H18A	0.459248	0.604074	0.585389	0.089*
H18B	0.420042	0.661406	0.526973	0.089*
N23	0.4738 (5)	0.4463 (5)	0.4966 (6)	0.0526 (17)
H23A	0.525148	0.506370	0.491147	0.063*
H23B	0.461581	0.414210	0.554047	0.063*
N14	0.6773 (7)	0.7997 (5)	0.6448 (6)	0.064 (2)
H14A	0.703660	0.864223	0.650496	0.077*
H14B	0.642530	0.768988	0.591066	0.077*
N24	0.7431 (6)	0.7956 (5)	0.7990 (6)	0.056 (2)
H24A	0.769089	0.860146	0.803928	0.067*
H24B	0.752004	0.762437	0.847556	0.067*
N27	0.5351 (5)	0.2599 (6)	0.5588 (6)	0.061 (2)
H27A	0.471036	0.217879	0.556338	0.073*
H27B	0.563723	0.285693	0.616693	0.073*
N13	0.4335 (7)	0.4534 (6)	0.3309 (6)	0.072 (3)
H13A	0.485127	0.513418	0.326244	0.086*
H13B	0.394786	0.426051	0.278581	0.086*
C7	0.5892 (6)	0.2845 (6)	0.4744 (6)	0.0403 (16)
C5	0.5800 (5)	0.6259 (5)	0.0469 (5)	0.0313 (14)
C8	0.3775 (6)	0.6391 (6)	0.6669 (6)	0.0423 (17)
C4	0.6902 (6)	0.7479 (6)	0.7182 (6)	0.0389 (16)
N15	0.5312 (5)	0.5742 (6)	−0.0364 (5)	0.0524 (19)
H15A	0.466081	0.542016	−0.037819	0.063*
H15B	0.564781	0.572856	−0.088995	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0309 (4)	0.0312 (4)	0.0320 (4)	0.0179 (3)	−0.0009 (3)	0.0001 (3)
Se2	0.0251 (3)	0.0351 (4)	0.0337 (4)	0.0143 (3)	0.0003 (3)	0.0033 (3)
Se3	0.0302 (4)	0.0244 (3)	0.0327 (4)	0.0120 (3)	0.0010 (3)	0.0008 (3)
Se4	0.0327 (4)	0.0258 (3)	0.0354 (5)	0.0123 (3)	0.0001 (3)	−0.0001 (3)
Se5	0.0255 (3)	0.0291 (3)	0.0346 (4)	0.0131 (3)	−0.0015 (3)	−0.0004 (3)
Se6	0.0285 (3)	0.0308 (3)	0.0340 (4)	0.0170 (3)	−0.0007 (3)	0.0001 (3)
Se7	0.0284 (4)	0.0371 (4)	0.0410 (5)	0.0047 (3)	−0.0022 (3)	0.0006 (3)
Se8	0.0417 (4)	0.0338 (4)	0.0352 (5)	0.0241 (3)	−0.0025 (3)	−0.0013 (3)
Se9	0.0286 (4)	0.0493 (5)	0.0477 (5)	0.0203 (4)	0.0049 (3)	0.0110 (4)
C6	0.032 (3)	0.032 (3)	0.038 (4)	0.020 (3)	−0.006 (3)	−0.003 (3)
C2	0.034 (4)	0.048 (4)	0.033 (4)	0.023 (3)	0.001 (3)	−0.002 (3)
C9	0.036 (3)	0.037 (4)	0.042 (5)	0.018 (3)	0.003 (3)	0.005 (3)
C3	0.041 (4)	0.032 (3)	0.034 (4)	0.013 (3)	0.003 (3)	−0.003 (3)
C1	0.036 (4)	0.036 (4)	0.027 (4)	0.017 (3)	0.000 (3)	0.002 (3)
N16	0.042 (3)	0.060 (4)	0.038 (4)	0.031 (3)	0.005 (3)	0.005 (3)
N21	0.038 (3)	0.073 (5)	0.041 (4)	0.032 (3)	0.003 (3)	−0.002 (3)
N19	0.040 (3)	0.082 (5)	0.038 (4)	0.039 (4)	0.005 (3)	0.003 (3)
N29	0.040 (4)	0.098 (6)	0.038 (4)	0.030 (4)	−0.004 (3)	−0.019 (4)
N22	0.047 (4)	0.177 (11)	0.037 (4)	0.066 (6)	−0.013 (3)	−0.024 (5)
N26	0.053 (4)	0.099 (6)	0.045 (4)	0.056 (4)	−0.001 (3)	0.006 (4)
N11	0.045 (3)	0.058 (4)	0.033 (3)	0.036 (3)	0.007 (3)	0.007 (3)
N12	0.078 (5)	0.082 (5)	0.036 (4)	0.066 (5)	0.007 (3)	0.012 (3)
N28	0.089 (6)	0.097 (6)	0.049 (5)	0.077 (6)	0.023 (4)	0.031 (4)
N25	0.034 (3)	0.061 (4)	0.044 (4)	0.019 (3)	0.007 (3)	−0.009 (3)
N17	0.035 (3)	0.060 (4)	0.046 (4)	0.006 (3)	0.005 (3)	−0.009 (3)
N18	0.091 (6)	0.146 (9)	0.038 (4)	0.100 (7)	0.024 (4)	0.032 (5)
N23	0.052 (4)	0.036 (3)	0.045 (4)	0.004 (3)	−0.003 (3)	−0.002 (3)
N14	0.107 (7)	0.036 (3)	0.046 (4)	0.034 (4)	−0.016 (4)	−0.003 (3)
N24	0.077 (5)	0.029 (3)	0.049 (4)	0.017 (3)	−0.012 (4)	−0.001 (3)
N27	0.032 (3)	0.082 (5)	0.048 (4)	0.013 (4)	0.000 (3)	−0.006 (4)
N13	0.093 (6)	0.036 (4)	0.041 (4)	−0.002 (4)	−0.012 (4)	0.002 (3)
C7	0.034 (4)	0.040 (4)	0.044 (4)	0.016 (3)	−0.004 (3)	−0.008 (3)
C5	0.032 (3)	0.031 (3)	0.028 (3)	0.014 (3)	0.000 (3)	0.002 (3)
C8	0.046 (4)	0.060 (5)	0.037 (4)	0.038 (4)	0.006 (3)	0.005 (3)
C4	0.048 (4)	0.034 (4)	0.032 (4)	0.018 (3)	0.007 (3)	0.001 (3)
N15	0.030 (3)	0.074 (5)	0.033 (4)	0.012 (3)	−0.002 (3)	−0.013 (3)

Geometric parameters (Å, º)

Se1—C1	1.867 (7)	N11—H11B	0.8600
Se2—C2	1.870 (7)	N12—H12A	0.8600
Se3—C3	1.877 (7)	N12—H12B	0.8600
Se4—C4	1.868 (7)	N28—H28A	0.8600
Se5—C5	1.862 (7)	N28—H28B	0.8600
Se6—C6	1.870 (6)	N28—C8	1.316 (11)
Se7—C7	1.869 (7)	N25—H25A	0.8600
Se8—C8	1.856 (7)	N25—H25B	0.8600
Se9—C9	1.873 (7)	N25—C5	1.323 (9)
C6—N16	1.319 (10)	N17—H17A	0.8600
C6—N26	1.318 (10)	N17—H17B	0.8600
C2—N21	1.307 (10)	N17—C7	1.335 (11)
C2—N22	1.295 (11)	N18—H18A	0.8600
C9—N19	1.307 (10)	N18—H18B	0.8600
C9—N29	1.299 (11)	N18—C8	1.322 (10)
C3—N23	1.309 (10)	N23—H23A	0.8600
C3—N13	1.306 (11)	N23—H23B	0.8600
C1—N11	1.313 (9)	N14—H14A	0.8600
C1—N12	1.326 (9)	N14—H14B	0.8600
N16—H16A	0.8600	N14—C4	1.313 (11)
N16—H16B	0.8600	N24—H24A	0.8600
N21—H21A	0.8600	N24—H24B	0.8600
N21—H21B	0.8600	N24—C4	1.303 (11)
N19—H19A	0.8600	N27—H27A	0.8600
N19—H19B	0.8600	N27—H27B	0.8600
N29—H29A	0.8600	N27—C7	1.310 (11)
N29—H29B	0.8600	N13—H13A	0.8600
N22—H22A	0.8600	N13—H13B	0.8600
N22—H22B	0.8600	C5—N15	1.327 (10)
N26—H26A	0.8600	N15—H15A	0.8600
N26—H26B	0.8600	N15—H15B	0.8600
N11—H11A	0.8600
N16—C6—Se6	120.5 (5)	C8—N28—H28B	120.0
N26—C6—Se6	120.7 (5)	H25A—N25—H25B	120.0
N26—C6—N16	118.8 (6)	C5—N25—H25A	120.0
N21—C2—Se2	120.6 (6)	C5—N25—H25B	120.0
N22—C2—Se2	119.9 (6)	H17A—N17—H17B	120.0
N22—C2—N21	119.4 (7)	C7—N17—H17A	120.0
N19—C9—Se9	120.6 (6)	C7—N17—H17B	120.0
N29—C9—Se9	120.8 (6)	H18A—N18—H18B	120.0
N29—C9—N19	118.6 (7)	C8—N18—H18A	120.0
N23—C3—Se3	120.5 (6)	C8—N18—H18B	120.0
N13—C3—Se3	120.1 (6)	C3—N23—H23A	120.0
N13—C3—N23	119.3 (7)	C3—N23—H23B	120.0
N11—C1—Se1	121.0 (5)	H23A—N23—H23B	120.0
N11—C1—N12	118.3 (7)	H14A—N14—H14B	120.0
N12—C1—Se1	120.7 (5)	C4—N14—H14A	120.0
C6—N16—H16A	120.0	C4—N14—H14B	120.0
C6—N16—H16B	120.0	H24A—N24—H24B	120.0
H16A—N16—H16B	120.0	C4—N24—H24A	120.0
C2—N21—H21A	120.0	C4—N24—H24B	120.0
C2—N21—H21B	120.0	H27A—N27—H27B	120.0
H21A—N21—H21B	120.0	C7—N27—H27A	120.0
C9—N19—H19A	120.0	C7—N27—H27B	120.0
C9—N19—H19B	120.0	C3—N13—H13A	120.0
H19A—N19—H19B	120.0	C3—N13—H13B	120.0
C9—N29—H29A	120.0	H13A—N13—H13B	120.0
C9—N29—H29B	120.0	N17—C7—Se7	120.4 (6)
H29A—N29—H29B	120.0	N27—C7—Se7	122.0 (6)
C2—N22—H22A	120.0	N27—C7—N17	117.6 (7)
C2—N22—H22B	120.0	N25—C5—Se5	121.3 (5)
H22A—N22—H22B	120.0	N25—C5—N15	118.7 (7)
C6—N26—H26A	120.0	N15—C5—Se5	120.0 (5)
C6—N26—H26B	120.0	N28—C8—Se8	121.3 (6)
H26A—N26—H26B	120.0	N28—C8—N18	117.6 (7)
C1—N11—H11A	120.0	N18—C8—Se8	121.1 (6)
C1—N11—H11B	120.0	N14—C4—Se4	120.1 (6)
H11A—N11—H11B	120.0	N24—C4—Se4	120.7 (6)
C1—N12—H12A	120.0	N24—C4—N14	119.2 (7)
C1—N12—H12B	120.0	C5—N15—H15A	120.0
H12A—N12—H12B	120.0	C5—N15—H15B	120.0
H28A—N28—H28B	120.0	H15A—N15—H15B	120.0
C8—N28—H28A	120.0

Selenourea (phase_alpha_Selenourea_270K)

Crystal data

CH4N2Se	Dx = 2.104 Mg m^−3
Mr = 123.02	Cu Kα radiation, λ = 1.54184 Å
Trigonal, P31	Cell parameters from 6632 reflections
a = 15.2541 (1) Å	θ = 3.3–72.2°
c = 13.0096 (2) Å	µ = 11.27 mm^−1
V = 2621.61 (5) Å^3	T = 270 K
Z = 27	Plate, orange
F(000) = 1566	0.25 × 0.10 × 0.05 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	4032 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	4001 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.036
Detector resolution: 10.5384 pixels mm^-1	θmax = 72.3°, θmin = 3.4°
ω scans	h = −18→18
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −18→16
Tmin = 0.395, Tmax = 1.000	l = −14→13
6907 measured reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0626P)^2 + 0.4992P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.033	(Δ/σ)max = 0.001
wR(F^2) = 0.090	Δρmax = 0.58 e Å^−3
S = 1.04	Δρmin = −0.46 e Å^−3
4032 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
326 parameters	Extinction coefficient: 0.00074 (6)
1 restraint	Absolute structure: Refined as a perfect inversion twin.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.5
Hydrogen site location: inferred from neighbouring sites

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component perfect inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	0.30619 (5)	0.35124 (6)	0.09711 (5)	0.03351 (18)
Se2	0.39488 (5)	0.36016 (6)	0.75804 (5)	0.03475 (19)
Se3	0.30496 (5)	0.27067 (5)	0.42659 (6)	0.03289 (17)
Se4	0.63092 (6)	0.60740 (6)	0.70710 (5)	0.0356 (2)
Se5	0.72101 (5)	0.69354 (5)	0.05079 (5)	0.03321 (18)
Se6	0.63372 (5)	0.70194 (6)	0.38297 (5)	0.03327 (18)
Se7	0.72868 (6)	0.37640 (6)	0.47389 (7)	0.0448 (2)
Se8	0.29817 (6)	0.70010 (5)	0.66440 (7)	0.0382 (2)
Se9	1.06991 (6)	1.02849 (7)	0.46008 (8)	0.0452 (2)
C6	0.7488 (5)	0.6885 (5)	0.3914 (6)	0.0365 (14)
C2	0.2571 (5)	0.3173 (6)	0.7564 (6)	0.0415 (16)
C9	0.9342 (5)	0.9962 (6)	0.4545 (6)	0.0412 (16)
C3	0.4131 (6)	0.4038 (5)	0.4178 (5)	0.0422 (16)
C1	0.3860 (5)	0.2904 (5)	0.0949 (5)	0.0369 (15)
N16	0.8035 (5)	0.6997 (5)	0.3095 (5)	0.0488 (15)
H16A	0.855917	0.692678	0.313924	0.059*
H16B	0.786954	0.714014	0.251296	0.059*
N21	0.2095 (5)	0.3156 (6)	0.8412 (5)	0.0544 (17)
H21A	0.146522	0.298239	0.839022	0.065*
H21B	0.241372	0.331927	0.898803	0.065*
N19	0.8899 (5)	1.0071 (6)	0.5362 (5)	0.0554 (18)
H19A	0.828075	0.993558	0.532820	0.066*
H19B	0.922760	1.027799	0.593065	0.066*
N29	0.8828 (5)	0.9649 (7)	0.3700 (6)	0.067 (2)
H29A	0.821003	0.951790	0.368213	0.081*
H29B	0.910399	0.957321	0.315673	0.081*
N22	0.2076 (6)	0.2924 (9)	0.6700 (6)	0.091 (4)
H22A	0.144666	0.275136	0.668826	0.109*
H22B	0.237941	0.293168	0.613927	0.109*
N26	0.7758 (6)	0.6665 (7)	0.4796 (5)	0.064 (2)
H26A	0.828505	0.659790	0.482559	0.077*
H26B	0.740853	0.658876	0.534095	0.077*
N11	0.4359 (5)	0.2926 (5)	0.0112 (5)	0.0458 (15)
H11A	0.471639	0.263329	0.010680	0.055*
H11B	0.432790	0.323377	−0.042894	0.055*
N12	0.3929 (6)	0.2421 (6)	0.1766 (5)	0.059 (2)
H12A	0.429174	0.213460	0.173910	0.071*
H12B	0.361144	0.239428	0.232143	0.071*
N28	0.3860 (7)	0.5964 (7)	0.7509 (6)	0.072 (3)
H28A	0.421495	0.566815	0.750360	0.086*
H28B	0.356275	0.597865	0.806502	0.086*
N25	0.5268 (5)	0.6267 (6)	0.1267 (6)	0.0534 (17)
H25A	0.461728	0.594530	0.123944	0.064*
H25B	0.557246	0.659740	0.181245	0.064*
N17	0.5417 (5)	0.2431 (6)	0.3861 (6)	0.059 (2)
H17A	0.477521	0.201391	0.386225	0.071*
H17B	0.575012	0.257637	0.329373	0.071*
N18	0.4242 (7)	0.6350 (8)	0.5839 (6)	0.082 (3)
H18A	0.459104	0.604877	0.585726	0.098*
H18B	0.419897	0.662345	0.527775	0.098*
N23	0.4729 (5)	0.4467 (5)	0.4967 (6)	0.0576 (18)
H23A	0.524141	0.506689	0.491063	0.069*
H23B	0.460792	0.414742	0.554128	0.069*
N14	0.6778 (7)	0.7997 (5)	0.6447 (6)	0.071 (2)
H14A	0.703298	0.864069	0.650903	0.085*
H14B	0.643957	0.769306	0.590458	0.085*
N24	0.7419 (6)	0.7952 (5)	0.7994 (6)	0.062 (2)
H24A	0.766950	0.859615	0.804544	0.074*
H24B	0.750832	0.762307	0.848028	0.074*
N27	0.5356 (5)	0.2608 (6)	0.5583 (6)	0.066 (2)
H27A	0.471601	0.218833	0.555730	0.080*
H27B	0.564115	0.286573	0.616145	0.080*
N13	0.4326 (7)	0.4534 (6)	0.3312 (6)	0.078 (3)
H13A	0.484091	0.513387	0.326448	0.094*
H13B	0.393901	0.426047	0.278816	0.094*
C7	0.5896 (6)	0.2853 (6)	0.4742 (6)	0.0442 (17)
C5	0.5799 (5)	0.6255 (5)	0.0470 (5)	0.0350 (14)
C8	0.3774 (6)	0.6392 (7)	0.6671 (6)	0.0465 (18)
C4	0.6905 (6)	0.7477 (5)	0.7182 (6)	0.0420 (16)
N15	0.5311 (5)	0.5739 (6)	−0.0364 (5)	0.0575 (19)
H15A	0.465978	0.542112	−0.037897	0.069*
H15B	0.564518	0.572338	−0.088875	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0340 (4)	0.0341 (4)	0.0356 (4)	0.0195 (3)	−0.0009 (3)	0.0000 (3)
Se2	0.0279 (3)	0.0381 (4)	0.0372 (4)	0.0157 (3)	0.0005 (3)	0.0037 (3)
Se3	0.0331 (4)	0.0270 (3)	0.0363 (4)	0.0133 (3)	0.0010 (3)	0.0009 (3)
Se4	0.0358 (4)	0.0282 (3)	0.0391 (5)	0.0133 (3)	0.0000 (3)	−0.0002 (3)
Se5	0.0284 (3)	0.0322 (3)	0.0385 (4)	0.0147 (3)	−0.0017 (3)	−0.0005 (3)
Se6	0.0314 (3)	0.0339 (3)	0.0378 (4)	0.0188 (3)	−0.0006 (3)	0.0003 (3)
Se7	0.0313 (4)	0.0403 (4)	0.0456 (5)	0.0051 (3)	−0.0026 (3)	0.0006 (3)
Se8	0.0457 (4)	0.0372 (4)	0.0395 (5)	0.0266 (3)	−0.0027 (3)	−0.0015 (3)
Se9	0.0313 (4)	0.0531 (5)	0.0522 (5)	0.0218 (4)	0.0050 (3)	0.0116 (4)
C6	0.036 (3)	0.037 (3)	0.042 (4)	0.021 (3)	−0.008 (3)	−0.004 (3)
C2	0.039 (4)	0.055 (4)	0.035 (4)	0.028 (3)	0.000 (3)	−0.004 (3)
C9	0.035 (3)	0.042 (4)	0.045 (4)	0.019 (3)	0.003 (3)	0.002 (3)
C3	0.048 (4)	0.034 (3)	0.035 (4)	0.014 (3)	0.004 (3)	−0.003 (3)
C1	0.036 (4)	0.039 (4)	0.034 (4)	0.017 (3)	−0.001 (3)	0.001 (3)
N16	0.044 (3)	0.066 (4)	0.045 (4)	0.035 (3)	0.005 (3)	0.005 (3)
N21	0.043 (3)	0.081 (5)	0.044 (4)	0.035 (4)	0.005 (3)	−0.002 (3)
N19	0.045 (3)	0.089 (5)	0.044 (4)	0.043 (4)	0.006 (3)	0.004 (3)
N29	0.041 (4)	0.109 (6)	0.043 (4)	0.032 (4)	−0.006 (3)	−0.024 (4)
N22	0.054 (4)	0.196 (12)	0.040 (4)	0.076 (6)	−0.012 (4)	−0.019 (6)
N26	0.065 (5)	0.111 (7)	0.045 (4)	0.066 (5)	0.002 (3)	0.010 (4)
N11	0.051 (4)	0.065 (4)	0.039 (3)	0.043 (3)	0.009 (3)	0.010 (3)
N12	0.087 (5)	0.089 (5)	0.039 (4)	0.073 (5)	0.008 (3)	0.013 (3)
N28	0.101 (6)	0.107 (7)	0.052 (5)	0.086 (6)	0.022 (4)	0.032 (5)
N25	0.037 (3)	0.067 (4)	0.048 (4)	0.020 (3)	0.006 (3)	−0.009 (3)
N17	0.038 (3)	0.064 (4)	0.051 (4)	0.008 (3)	0.003 (3)	−0.011 (3)
N18	0.099 (6)	0.160 (9)	0.044 (4)	0.108 (7)	0.028 (4)	0.035 (5)
N23	0.056 (4)	0.041 (3)	0.051 (4)	0.005 (3)	−0.005 (3)	−0.003 (3)
N14	0.118 (7)	0.040 (3)	0.051 (4)	0.036 (4)	−0.020 (4)	−0.004 (3)
N24	0.086 (5)	0.032 (3)	0.055 (5)	0.019 (3)	−0.013 (4)	−0.003 (3)
N27	0.035 (3)	0.087 (6)	0.052 (4)	0.012 (3)	0.002 (3)	−0.006 (4)
N13	0.096 (6)	0.040 (4)	0.047 (4)	−0.005 (4)	−0.012 (4)	0.004 (3)
C7	0.036 (3)	0.044 (4)	0.049 (4)	0.017 (3)	−0.005 (3)	−0.007 (3)
C5	0.033 (3)	0.035 (3)	0.033 (3)	0.015 (3)	−0.002 (3)	0.001 (3)
C8	0.048 (4)	0.067 (5)	0.039 (4)	0.040 (4)	0.007 (3)	0.005 (3)
C4	0.054 (4)	0.037 (3)	0.032 (4)	0.021 (3)	0.006 (3)	0.000 (3)
N15	0.035 (3)	0.080 (5)	0.039 (4)	0.015 (3)	−0.002 (3)	−0.015 (3)

Geometric parameters (Å, º)

Se1—C1	1.864 (7)	N11—H11B	0.8600
Se2—C2	1.864 (7)	N12—H12A	0.8600
Se3—C3	1.873 (7)	N12—H12B	0.8600
Se4—C4	1.866 (7)	N28—H28A	0.8600
Se5—C5	1.865 (7)	N28—H28B	0.8600
Se6—C6	1.869 (6)	N28—C8	1.312 (11)
Se7—C7	1.866 (7)	N25—H25A	0.8600
Se8—C8	1.857 (7)	N25—H25B	0.8600
Se9—C9	1.874 (7)	N25—C5	1.322 (9)
C6—N16	1.312 (10)	N17—H17A	0.8600
C6—N26	1.318 (9)	N17—H17B	0.8600
C2—N21	1.313 (10)	N17—C7	1.339 (11)
C2—N22	1.300 (11)	N18—H18A	0.8600
C9—N19	1.313 (10)	N18—H18B	0.8600
C9—N29	1.296 (10)	N18—C8	1.315 (10)
C3—N23	1.310 (10)	N23—H23A	0.8600
C3—N13	1.306 (11)	N23—H23B	0.8600
C1—N11	1.320 (9)	N14—H14A	0.8600
C1—N12	1.327 (9)	N14—H14B	0.8600
N16—H16A	0.8600	N14—C4	1.317 (11)
N16—H16B	0.8600	N24—H24A	0.8600
N21—H21A	0.8600	N24—H24B	0.8600
N21—H21B	0.8600	N24—C4	1.299 (10)
N19—H19A	0.8600	N27—H27A	0.8600
N19—H19B	0.8600	N27—H27B	0.8600
N29—H29A	0.8600	N27—C7	1.306 (11)
N29—H29B	0.8600	N13—H13A	0.8600
N22—H22A	0.8600	N13—H13B	0.8600
N22—H22B	0.8600	C5—N15	1.329 (10)
N26—H26A	0.8600	N15—H15A	0.8600
N26—H26B	0.8600	N15—H15B	0.8600
N11—H11A	0.8600
N16—C6—Se6	120.6 (5)	C8—N28—H28B	120.0
N16—C6—N26	118.7 (6)	H25A—N25—H25B	120.0
N26—C6—Se6	120.7 (5)	C5—N25—H25A	120.0
N21—C2—Se2	120.8 (6)	C5—N25—H25B	120.0
N22—C2—Se2	120.0 (6)	H17A—N17—H17B	120.0
N22—C2—N21	119.1 (7)	C7—N17—H17A	120.0
N19—C9—Se9	120.4 (6)	C7—N17—H17B	120.0
N29—C9—Se9	121.0 (6)	H18A—N18—H18B	120.0
N29—C9—N19	118.6 (7)	C8—N18—H18A	120.0
N23—C3—Se3	120.6 (6)	C8—N18—H18B	120.0
N13—C3—Se3	120.2 (6)	C3—N23—H23A	120.0
N13—C3—N23	119.2 (7)	C3—N23—H23B	120.0
N11—C1—Se1	120.8 (5)	H23A—N23—H23B	120.0
N11—C1—N12	118.0 (6)	H14A—N14—H14B	120.0
N12—C1—Se1	121.2 (5)	C4—N14—H14A	120.0
C6—N16—H16A	120.0	C4—N14—H14B	120.0
C6—N16—H16B	120.0	H24A—N24—H24B	120.0
H16A—N16—H16B	120.0	C4—N24—H24A	120.0
C2—N21—H21A	120.0	C4—N24—H24B	120.0
C2—N21—H21B	120.0	H27A—N27—H27B	120.0
H21A—N21—H21B	120.0	C7—N27—H27A	120.0
C9—N19—H19A	120.0	C7—N27—H27B	120.0
C9—N19—H19B	120.0	C3—N13—H13A	120.0
H19A—N19—H19B	120.0	C3—N13—H13B	120.0
C9—N29—H29A	120.0	H13A—N13—H13B	120.0
C9—N29—H29B	120.0	N17—C7—Se7	120.0 (6)
H29A—N29—H29B	120.0	N27—C7—Se7	122.3 (6)
C2—N22—H22A	120.0	N27—C7—N17	117.7 (7)
C2—N22—H22B	120.0	N25—C5—Se5	121.1 (5)
H22A—N22—H22B	120.0	N25—C5—N15	118.9 (6)
C6—N26—H26A	120.0	N15—C5—Se5	120.0 (5)
C6—N26—H26B	120.0	N28—C8—Se8	121.2 (6)
H26A—N26—H26B	120.0	N28—C8—N18	117.9 (7)
C1—N11—H11A	120.0	N18—C8—Se8	120.9 (6)
C1—N11—H11B	120.0	N14—C4—Se4	120.0 (6)
H11A—N11—H11B	120.0	N24—C4—Se4	121.0 (6)
C1—N12—H12A	120.0	N24—C4—N14	118.9 (7)
C1—N12—H12B	120.0	C5—N15—H15A	120.0
H12A—N12—H12B	120.0	C5—N15—H15B	120.0
H28A—N28—H28B	120.0	H15A—N15—H15B	120.0
C8—N28—H28A	120.0

Selenourea (phase_alpha_Selenourea_290K)

Crystal data

CH4N2Se	Dx = 2.097 Mg m^−3
Mr = 123.02	Cu Kα radiation, λ = 1.54184 Å
Trigonal, P31	Cell parameters from 3720 reflections
a = 15.2714 (1) Å	θ = 3.3–72.3°
c = 13.0219 (2) Å	µ = 11.23 mm^−1
V = 2630.04 (5) Å^3	T = 290 K
Z = 27	Plate, orange
F(000) = 1566	0.25 × 0.10 × 0.05 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	2709 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	2649 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.030
Detector resolution: 10.5384 pixels mm^-1	θmax = 72.5°, θmin = 3.3°
ω scans	h = −12→15
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −18→11
Tmin = 0.279, Tmax = 1.000	l = −13→11
3810 measured reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0775P)^2] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.035	(Δ/σ)max < 0.001
wR(F^2) = 0.102	Δρmax = 0.46 e Å^−3
S = 1.06	Δρmin = −0.45 e Å^−3
2709 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
326 parameters	Extinction coefficient: 0.00075 (8)
1 restraint	Absolute structure: Refined as a perfect inversion twin.
Primary atom site location: dual	Absolute structure parameter: 0.5
Hydrogen site location: inferred from neighbouring sites

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component perfect inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	0.30605 (7)	0.35124 (8)	0.09725 (8)	0.0377 (3)
Se2	0.39435 (8)	0.36028 (8)	0.75790 (8)	0.0392 (3)
Se3	0.30499 (8)	0.27089 (7)	0.42680 (8)	0.0374 (3)
Se4	0.63085 (8)	0.60744 (8)	0.70707 (8)	0.0403 (3)
Se5	0.72109 (7)	0.69330 (7)	0.05065 (8)	0.0375 (3)
Se6	0.63390 (8)	0.70196 (8)	0.38297 (7)	0.0376 (3)
Se7	0.72901 (8)	0.37619 (9)	0.47311 (10)	0.0502 (3)
Se8	0.29809 (8)	0.70028 (8)	0.66470 (10)	0.0435 (3)
Se9	1.07005 (8)	1.02909 (9)	0.46070 (11)	0.0504 (3)
C6	0.7477 (7)	0.6871 (7)	0.3908 (8)	0.041 (2)
C2	0.2565 (8)	0.3166 (8)	0.7571 (8)	0.047 (3)
C9	0.9342 (7)	0.9967 (8)	0.4554 (9)	0.047 (2)
C3	0.4136 (8)	0.4044 (7)	0.4174 (9)	0.050 (3)
C1	0.3857 (7)	0.2909 (7)	0.0947 (8)	0.043 (2)
N16	0.8034 (7)	0.6989 (7)	0.3088 (7)	0.056 (2)
H16A	0.855472	0.691494	0.313505	0.067*
H16B	0.787520	0.713938	0.250704	0.067*
N21	0.2090 (7)	0.3148 (8)	0.8412 (7)	0.058 (2)
H21A	0.145638	0.295719	0.839138	0.070*
H21B	0.241042	0.332702	0.898619	0.070*
N19	0.8895 (7)	1.0064 (8)	0.5363 (7)	0.063 (3)
H19A	0.827086	0.990618	0.533080	0.076*
H19B	0.922490	1.028594	0.592797	0.076*
N29	0.8831 (7)	0.9631 (10)	0.3712 (8)	0.077 (3)
H29A	0.820669	0.947651	0.369291	0.092*
H29B	0.911482	0.956244	0.317191	0.092*
N22	0.2071 (8)	0.2894 (12)	0.6712 (9)	0.105 (5)
H22A	0.143754	0.270412	0.670068	0.126*
H22B	0.237616	0.290233	0.615422	0.126*
N26	0.7740 (8)	0.6638 (9)	0.4796 (8)	0.076 (3)
H26A	0.826342	0.656694	0.482805	0.092*
H26B	0.738583	0.655770	0.533824	0.092*
N11	0.4346 (6)	0.2919 (7)	0.0104 (7)	0.052 (2)
H11A	0.468767	0.261123	0.009393	0.062*
H11B	0.432254	0.323473	−0.043273	0.062*
N12	0.3912 (9)	0.2408 (8)	0.1770 (7)	0.067 (3)
H12A	0.425851	0.210565	0.174006	0.081*
H12B	0.360026	0.238984	0.232677	0.081*
N28	0.3853 (9)	0.5961 (9)	0.7511 (9)	0.079 (4)
H28A	0.420135	0.566021	0.750512	0.095*
H28B	0.355275	0.597494	0.806451	0.095*
N25	0.5275 (7)	0.6272 (8)	0.1268 (8)	0.060 (3)
H25A	0.462589	0.595564	0.123985	0.072*
H25B	0.558049	0.659836	0.181508	0.072*
N17	0.5419 (7)	0.2429 (8)	0.3856 (7)	0.062 (3)
H17A	0.477669	0.201968	0.386189	0.074*
H17B	0.574898	0.256174	0.328826	0.074*
N18	0.4253 (9)	0.6355 (11)	0.5848 (8)	0.092 (4)
H18A	0.459413	0.604694	0.587200	0.111*
H18B	0.422111	0.663304	0.528550	0.111*
N23	0.4721 (7)	0.4479 (7)	0.4957 (7)	0.063 (3)
H23A	0.521109	0.509131	0.490809	0.076*
H23B	0.461814	0.415363	0.552482	0.076*
N14	0.6786 (9)	0.7994 (7)	0.6443 (8)	0.080 (4)
H14A	0.704720	0.863790	0.650055	0.096*
H14B	0.644726	0.768902	0.590215	0.096*
N24	0.7411 (9)	0.7942 (7)	0.7989 (8)	0.074 (3)
H24A	0.766845	0.858639	0.803502	0.089*
H24B	0.749421	0.761294	0.847857	0.089*
N27	0.5365 (7)	0.2629 (8)	0.5572 (8)	0.078 (3)
H27A	0.472358	0.221771	0.555636	0.093*
H27B	0.565838	0.289492	0.614506	0.093*
N13	0.4304 (9)	0.4550 (7)	0.3317 (8)	0.092 (5)
H13A	0.479705	0.516240	0.327821	0.110*
H13B	0.392238	0.427052	0.279325	0.110*
C7	0.5899 (8)	0.2853 (8)	0.4720 (9)	0.051 (3)
C5	0.5810 (7)	0.6258 (7)	0.0465 (8)	0.040 (2)
C8	0.3778 (8)	0.6400 (9)	0.6672 (10)	0.056 (3)
C4	0.6904 (9)	0.7472 (8)	0.7188 (9)	0.053 (3)
N15	0.5309 (6)	0.5745 (8)	−0.0369 (7)	0.068 (3)
H15A	0.465922	0.543392	−0.037810	0.081*
H15B	0.563646	0.572392	−0.089689	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0370 (5)	0.0381 (5)	0.0418 (6)	0.0216 (5)	−0.0012 (4)	0.0002 (4)
Se2	0.0300 (5)	0.0413 (6)	0.0448 (7)	0.0167 (4)	0.0000 (4)	0.0038 (4)
Se3	0.0367 (5)	0.0300 (5)	0.0429 (6)	0.0148 (4)	0.0014 (4)	0.0013 (4)
Se4	0.0396 (5)	0.0315 (5)	0.0460 (7)	0.0148 (4)	0.0001 (5)	0.0004 (4)
Se5	0.0312 (5)	0.0356 (5)	0.0452 (6)	0.0162 (4)	−0.0018 (4)	−0.0005 (4)
Se6	0.0352 (5)	0.0373 (5)	0.0442 (6)	0.0210 (4)	−0.0006 (4)	0.0001 (4)
Se7	0.0347 (6)	0.0443 (6)	0.0528 (8)	0.0058 (4)	−0.0027 (5)	0.0010 (5)
Se8	0.0509 (6)	0.0412 (6)	0.0467 (7)	0.0293 (5)	−0.0035 (5)	−0.0020 (4)
Se9	0.0346 (5)	0.0575 (7)	0.0600 (8)	0.0237 (5)	0.0043 (5)	0.0113 (6)
C6	0.042 (5)	0.040 (5)	0.048 (6)	0.024 (4)	−0.005 (4)	−0.005 (4)
C2	0.041 (5)	0.060 (6)	0.045 (7)	0.028 (5)	0.005 (5)	0.007 (5)
C9	0.035 (5)	0.050 (6)	0.057 (8)	0.023 (4)	0.001 (5)	0.004 (5)
C3	0.053 (6)	0.034 (5)	0.052 (7)	0.014 (5)	0.001 (5)	−0.012 (5)
C1	0.038 (5)	0.037 (5)	0.051 (7)	0.018 (4)	0.001 (4)	0.002 (4)
N16	0.051 (5)	0.079 (6)	0.049 (6)	0.042 (5)	0.005 (4)	0.003 (4)
N21	0.046 (5)	0.092 (7)	0.045 (6)	0.040 (5)	0.004 (4)	−0.003 (5)
N19	0.050 (5)	0.106 (8)	0.051 (6)	0.053 (5)	0.008 (4)	0.001 (5)
N29	0.048 (5)	0.127 (10)	0.053 (8)	0.042 (6)	−0.006 (5)	−0.028 (6)
N22	0.058 (6)	0.231 (17)	0.044 (7)	0.086 (9)	−0.011 (6)	−0.016 (9)
N26	0.074 (7)	0.138 (10)	0.055 (7)	0.081 (7)	0.009 (5)	0.023 (6)
N11	0.056 (5)	0.073 (6)	0.047 (6)	0.048 (5)	0.006 (4)	0.005 (4)
N12	0.094 (8)	0.100 (8)	0.048 (6)	0.079 (7)	0.009 (5)	0.015 (5)
N28	0.111 (9)	0.125 (10)	0.059 (7)	0.101 (8)	0.027 (6)	0.029 (7)
N25	0.039 (4)	0.081 (7)	0.048 (6)	0.021 (5)	0.004 (4)	−0.013 (5)
N17	0.041 (5)	0.079 (7)	0.037 (6)	0.009 (5)	−0.004 (4)	−0.008 (5)
N18	0.098 (9)	0.184 (14)	0.056 (7)	0.116 (10)	0.021 (6)	0.027 (8)
N23	0.061 (5)	0.045 (5)	0.053 (6)	0.003 (4)	−0.013 (5)	−0.007 (4)
N14	0.138 (11)	0.040 (5)	0.058 (6)	0.042 (6)	−0.027 (7)	−0.005 (4)
N24	0.106 (9)	0.034 (4)	0.065 (8)	0.023 (5)	−0.027 (7)	−0.004 (4)
N27	0.040 (5)	0.104 (9)	0.053 (7)	0.010 (5)	−0.004 (4)	−0.005 (6)
N13	0.127 (11)	0.038 (5)	0.043 (7)	−0.009 (6)	−0.013 (6)	0.004 (4)
C7	0.037 (5)	0.046 (6)	0.061 (8)	0.013 (4)	−0.001 (5)	−0.001 (5)
C5	0.031 (4)	0.034 (4)	0.051 (7)	0.015 (4)	−0.003 (4)	0.002 (4)
C8	0.047 (6)	0.077 (8)	0.060 (8)	0.044 (6)	0.006 (5)	0.007 (6)
C4	0.054 (6)	0.043 (6)	0.061 (8)	0.024 (5)	0.002 (5)	−0.004 (5)
N15	0.033 (4)	0.092 (7)	0.052 (7)	0.011 (5)	−0.005 (4)	−0.016 (5)

Geometric parameters (Å, º)

Se1—C1	1.857 (10)	N11—H11B	0.8600
Se2—C2	1.863 (10)	N12—H12A	0.8600
Se3—C3	1.882 (10)	N12—H12B	0.8600
Se4—C4	1.861 (11)	N28—H28A	0.8600
Se5—C5	1.854 (9)	N28—H28B	0.8600
Se6—C6	1.865 (9)	N28—C8	1.316 (15)
Se7—C7	1.869 (10)	N25—H25A	0.8600
Se8—C8	1.857 (10)	N25—H25B	0.8600
Se9—C9	1.878 (9)	N25—C5	1.333 (13)
C6—N16	1.319 (13)	N17—H17A	0.8600
C6—N26	1.330 (12)	N17—H17B	0.8600
C2—N21	1.307 (13)	N17—C7	1.321 (14)
C2—N22	1.296 (15)	N18—H18A	0.8600
C9—N19	1.303 (13)	N18—H18B	0.8600
C9—N29	1.294 (14)	N18—C8	1.316 (15)
C3—N23	1.298 (13)	N23—H23A	0.8600
C3—N13	1.307 (14)	N23—H23B	0.8600
C1—N11	1.323 (13)	N14—H14A	0.8600
C1—N12	1.344 (13)	N14—H14B	0.8600
N16—H16A	0.8600	N14—C4	1.324 (15)
N16—H16B	0.8600	N24—H24A	0.8600
N21—H21A	0.8600	N24—H24B	0.8600
N21—H21B	0.8600	N24—C4	1.283 (15)
N19—H19A	0.8600	N27—H27A	0.8600
N19—H19B	0.8600	N27—H27B	0.8600
N29—H29A	0.8600	N27—C7	1.317 (15)
N29—H29B	0.8600	N13—H13A	0.8600
N22—H22A	0.8600	N13—H13B	0.8600
N22—H22B	0.8600	C5—N15	1.334 (13)
N26—H26A	0.8600	N15—H15A	0.8600
N26—H26B	0.8600	N15—H15B	0.8600
N11—H11A	0.8600
N16—C6—Se6	121.0 (7)	C8—N28—H28B	120.0
N16—C6—N26	118.7 (8)	H25A—N25—H25B	120.0
N26—C6—Se6	120.3 (7)	C5—N25—H25A	120.0
N21—C2—Se2	121.3 (8)	C5—N25—H25B	120.0
N22—C2—Se2	119.5 (8)	H17A—N17—H17B	120.0
N22—C2—N21	119.2 (10)	C7—N17—H17A	120.0
N19—C9—Se9	120.9 (8)	C7—N17—H17B	120.0
N29—C9—Se9	120.3 (8)	H18A—N18—H18B	120.0
N29—C9—N19	118.9 (9)	C8—N18—H18A	120.0
N23—C3—Se3	120.7 (8)	C8—N18—H18B	120.0
N23—C3—N13	119.1 (9)	C3—N23—H23A	120.0
N13—C3—Se3	120.1 (8)	C3—N23—H23B	120.0
N11—C1—Se1	121.0 (8)	H23A—N23—H23B	120.0
N11—C1—N12	118.2 (9)	H14A—N14—H14B	120.0
N12—C1—Se1	120.7 (8)	C4—N14—H14A	120.0
C6—N16—H16A	120.0	C4—N14—H14B	120.0
C6—N16—H16B	120.0	H24A—N24—H24B	120.0
H16A—N16—H16B	120.0	C4—N24—H24A	120.0
C2—N21—H21A	120.0	C4—N24—H24B	120.0
C2—N21—H21B	120.0	H27A—N27—H27B	120.0
H21A—N21—H21B	120.0	C7—N27—H27A	120.0
C9—N19—H19A	120.0	C7—N27—H27B	120.0
C9—N19—H19B	120.0	C3—N13—H13A	120.0
H19A—N19—H19B	120.0	C3—N13—H13B	120.0
C9—N29—H29A	120.0	H13A—N13—H13B	120.0
C9—N29—H29B	120.0	N17—C7—Se7	121.1 (8)
H29A—N29—H29B	120.0	N27—C7—Se7	120.8 (8)
C2—N22—H22A	120.0	N27—C7—N17	118.1 (9)
C2—N22—H22B	120.0	N25—C5—Se5	120.9 (7)
H22A—N22—H22B	120.0	N15—C5—Se5	120.9 (7)
C6—N26—H26A	120.0	N15—C5—N25	118.2 (8)
C6—N26—H26B	120.0	N28—C8—Se8	120.8 (8)
H26A—N26—H26B	120.0	N28—C8—N18	117.3 (9)
C1—N11—H11A	120.0	N18—C8—Se8	121.8 (9)
C1—N11—H11B	120.0	N14—C4—Se4	119.7 (9)
H11A—N11—H11B	120.0	N24—C4—Se4	121.4 (9)
C1—N12—H12A	120.0	N24—C4—N14	119.0 (10)
C1—N12—H12B	120.0	C5—N15—H15A	120.0
H12A—N12—H12B	120.0	C5—N15—H15B	120.0
H28A—N28—H28B	120.0	H15A—N15—H15B	120.0
C8—N28—H28A	120.0

Selenourea (phase_alpha_Selenourea_293K)

Crystal data

CH4N2Se	Dx = 2.113 Mg m^−3
Mr = 123.02	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P31	Cell parameters from 3420 reflections
a = 15.2757 (6) Å	θ = 3.4–28.8°
c = 13.0230 (5) Å	µ = 9.48 mm^−1
V = 2631.7 (2) Å^3	T = 293 K
Z = 27	Plate, orange
F(000) = 1566	0.25 × 0.10 × 0.05 mm

Data collection

Xcalibur, Eos diffractometer	7257 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	5372 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 16.1544 pixels mm^-1	θmax = 29.1°, θmin = 3.1°
ω scans	h = −18→20
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −19→19
Tmin = 0.550, Tmax = 1.000	l = −17→16
18848 measured reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + 51.6018P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.081	(Δ/σ)max < 0.001
wR(F^2) = 0.143	Δρmax = 1.74 e Å^−3
S = 1.09	Δρmin = −2.14 e Å^−3
7257 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
326 parameters	Extinction coefficient: 0.00068 (4)
1 restraint	Absolute structure: Refined as a perfect inversion twin.
Primary atom site location: dual	Absolute structure parameter: 0.5
Hydrogen site location: inferred from neighbouring sites

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component perfect inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	0.30586 (19)	0.35118 (18)	0.09687 (17)	0.0324 (5)
Se2	0.39446 (19)	0.3609 (2)	0.75598 (17)	0.0349 (6)
Se3	0.30425 (19)	0.27047 (18)	0.42822 (19)	0.0330 (5)
Se4	0.6316 (2)	0.6083 (2)	0.70798 (17)	0.0413 (7)
Se5	0.72099 (19)	0.6936 (2)	0.05018 (19)	0.0358 (6)
Se6	0.63414 (18)	0.7016 (2)	0.38280 (17)	0.0319 (5)
Se7	0.7307 (2)	0.3744 (2)	0.47012 (19)	0.0502 (3)
Se8	0.29956 (19)	0.70090 (19)	0.6651 (2)	0.0389 (6)
Se9	1.0696 (2)	1.0306 (2)	0.4653 (2)	0.0504 (3)
C6	0.7471 (17)	0.6824 (17)	0.3878 (16)	0.033 (5)
C2	0.257 (3)	0.321 (3)	0.762 (2)	0.076 (11)
C9	0.923 (3)	0.985 (2)	0.461 (2)	0.047 (2)
C3	0.413 (2)	0.4015 (17)	0.4161 (16)	0.042 (6)
C1	0.3823 (19)	0.287 (2)	0.0930 (16)	0.069 (7)
N16	0.8026 (14)	0.6950 (16)	0.3098 (15)	0.049 (5)
H16A	0.853367	0.685507	0.315047	0.058*
H16B	0.789258	0.712914	0.251984	0.058*
N21	0.2095 (18)	0.315 (3)	0.8419 (16)	0.058 (2)
H21A	0.145477	0.292744	0.839090	0.070*
H21B	0.240685	0.333944	0.899690	0.070*
N19	0.889 (2)	0.998 (2)	0.537 (2)	0.063 (3)
H19A	0.832966	0.998036	0.534709	0.076*
H19B	0.920701	1.007752	0.594164	0.076*
N29	0.8880 (16)	0.970 (2)	0.3758 (18)	0.077 (3)
H29A	0.831657	0.969009	0.365686	0.092*
H29B	0.918923	0.961568	0.325249	0.092*
N22	0.205 (3)	0.290 (4)	0.670 (2)	0.069 (7)
H22A	0.140641	0.267732	0.669481	0.083*
H22B	0.235784	0.292962	0.614210	0.083*
N26	0.7657 (18)	0.655 (2)	0.4783 (15)	0.065 (7)
H26A	0.816076	0.644833	0.485105	0.078*
H26B	0.727262	0.646603	0.529930	0.078*
N11	0.4329 (14)	0.2940 (15)	0.0085 (13)	0.041 (5)
H11A	0.471462	0.267963	0.006228	0.049*
H11B	0.427415	0.324611	−0.044418	0.049*
N12	0.3902 (18)	0.241 (2)	0.1738 (14)	0.067 (3)
H12A	0.428647	0.214368	0.172002	0.081*
H12B	0.357021	0.236206	0.228710	0.081*
N28	0.393 (2)	0.6031 (19)	0.7539 (15)	0.079 (4)
H28A	0.431740	0.577378	0.749818	0.095*
H28B	0.366026	0.603537	0.811742	0.095*
N25	0.5269 (14)	0.6214 (16)	0.1298 (14)	0.069 (7)
H25A	0.462246	0.594241	0.126288	0.083*
H25B	0.557882	0.648591	0.186170	0.083*
N17	0.5407 (15)	0.2465 (18)	0.391 (2)	0.062 (3)
H17A	0.475688	0.214297	0.391154	0.074*
H17B	0.573188	0.251500	0.335570	0.074*
N18	0.425 (2)	0.636 (3)	0.5816 (15)	0.069 (7)
H18A	0.462331	0.608409	0.584775	0.083*
H18B	0.417380	0.658942	0.524245	0.083*
N23	0.4734 (18)	0.4482 (18)	0.4943 (17)	0.069 (7)
H23A	0.519956	0.510472	0.488604	0.083*
H23B	0.466258	0.416400	0.550970	0.083*
N14	0.680 (3)	0.797 (2)	0.6445 (19)	0.122 (15)
H14A	0.701368	0.861111	0.645417	0.146*
H14B	0.647645	0.761737	0.591845	0.146*
N24	0.739 (3)	0.793 (2)	0.7993 (19)	0.100 (11)
H24A	0.764295	0.856282	0.810039	0.121*
H24B	0.744834	0.755312	0.845229	0.121*
N27	0.539 (2)	0.278 (3)	0.555 (2)	0.128 (16)
H27A	0.473899	0.245628	0.553526	0.154*
H27B	0.570145	0.304735	0.611472	0.154*
N13	0.430 (2)	0.4571 (17)	0.3313 (17)	0.069 (7)
H13A	0.477394	0.519116	0.330258	0.083*
H13B	0.392465	0.430839	0.277798	0.083*
C7	0.589 (2)	0.287 (2)	0.4737 (19)	0.054 (7)
C5	0.5826 (14)	0.6213 (16)	0.0422 (15)	0.027 (4)
C8	0.375 (3)	0.642 (3)	0.672 (2)	0.078 (11)
C4	0.696 (2)	0.756 (3)	0.7201 (16)	0.053 (3)
N15	0.5294 (16)	0.5787 (18)	−0.0392 (16)	0.068 (3)
H15A	0.464790	0.552818	−0.037686	0.081*
H15B	0.558589	0.576177	−0.094617	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0355 (13)	0.0303 (12)	0.0329 (11)	0.0175 (11)	−0.0026 (10)	0.0031 (10)
Se2	0.0303 (13)	0.0375 (13)	0.0375 (13)	0.0175 (11)	−0.0049 (10)	−0.0024 (10)
Se3	0.0339 (13)	0.0278 (12)	0.0317 (10)	0.0112 (11)	0.0043 (10)	0.0005 (10)
Se4	0.0430 (14)	0.0356 (14)	0.0414 (15)	0.0168 (12)	−0.0050 (11)	−0.0042 (10)
Se5	0.0315 (12)	0.0408 (13)	0.0378 (13)	0.0200 (11)	0.0022 (10)	0.0052 (10)
Se6	0.0348 (12)	0.0347 (12)	0.0326 (12)	0.0222 (10)	−0.0023 (10)	−0.0028 (9)
Se7	0.0347 (6)	0.0443 (6)	0.0528 (8)	0.0058 (4)	−0.0027 (5)	0.0010 (5)
Se8	0.0499 (15)	0.0416 (14)	0.0355 (13)	0.0304 (12)	−0.0065 (11)	−0.0028 (11)
Se9	0.0346 (5)	0.0575 (7)	0.0600 (8)	0.0237 (5)	0.0043 (5)	0.0113 (6)
C6	0.035 (11)	0.040 (12)	0.037 (11)	0.029 (11)	0.001 (9)	−0.001 (9)
C2	0.12 (3)	0.11 (3)	0.043 (15)	0.09 (2)	−0.048 (18)	−0.044 (17)
C9	0.035 (5)	0.050 (6)	0.057 (8)	0.023 (4)	0.001 (5)	0.004 (5)
C3	0.064 (16)	0.033 (12)	0.021 (10)	0.018 (11)	−0.005 (10)	0.003 (9)
C1	0.067 (16)	0.059 (15)	0.047 (13)	0.006 (13)	0.000 (12)	−0.016 (11)
N16	0.031 (10)	0.080 (16)	0.049 (12)	0.037 (11)	−0.003 (9)	0.000 (11)
N21	0.046 (5)	0.092 (7)	0.045 (6)	0.040 (5)	0.004 (4)	−0.003 (5)
N19	0.050 (5)	0.106 (8)	0.051 (6)	0.053 (5)	0.008 (4)	0.001 (5)
N29	0.048 (5)	0.127 (10)	0.053 (8)	0.042 (6)	−0.006 (5)	−0.028 (6)
N22	0.067 (16)	0.059 (15)	0.047 (13)	0.006 (13)	0.000 (12)	−0.016 (11)
N26	0.082 (17)	0.13 (2)	0.036 (11)	0.088 (17)	−0.006 (11)	0.012 (13)
N11	0.051 (12)	0.056 (12)	0.026 (9)	0.036 (11)	0.002 (8)	0.006 (9)
N12	0.094 (8)	0.100 (8)	0.048 (6)	0.079 (7)	0.009 (5)	0.015 (5)
N28	0.111 (9)	0.125 (10)	0.059 (7)	0.101 (8)	0.027 (6)	0.029 (7)
N25	0.067 (16)	0.059 (15)	0.047 (13)	0.006 (13)	0.000 (12)	−0.016 (11)
N17	0.041 (5)	0.079 (7)	0.037 (6)	0.009 (5)	−0.004 (4)	−0.008 (5)
N18	0.067 (16)	0.059 (15)	0.047 (13)	0.006 (13)	0.000 (12)	−0.016 (11)
N23	0.067 (16)	0.059 (15)	0.047 (13)	0.006 (13)	0.000 (12)	−0.016 (11)
N14	0.24 (4)	0.055 (17)	0.047 (15)	0.06 (2)	−0.03 (2)	−0.021 (13)
N24	0.16 (3)	0.067 (19)	0.058 (17)	0.05 (2)	−0.021 (19)	0.002 (14)
N27	0.056 (18)	0.26 (5)	0.059 (18)	0.07 (2)	0.017 (14)	0.04 (2)
N13	0.067 (16)	0.059 (15)	0.047 (13)	0.006 (13)	0.000 (12)	−0.016 (11)
C7	0.053 (16)	0.10 (2)	0.046 (14)	0.062 (17)	−0.006 (12)	−0.003 (15)
C5	0.017 (9)	0.034 (11)	0.029 (10)	0.011 (9)	0.014 (8)	0.004 (9)
C8	0.12 (3)	0.15 (3)	0.038 (14)	0.12 (3)	0.005 (16)	0.010 (17)
C4	0.054 (6)	0.043 (6)	0.061 (8)	0.024 (5)	0.002 (5)	−0.004 (5)
N15	0.033 (4)	0.092 (7)	0.052 (7)	0.011 (5)	−0.005 (4)	−0.016 (5)

Geometric parameters (Å, º)

Se1—C1	1.86 (2)	N11—H11B	0.8600
Se2—C2	1.87 (3)	N12—H12A	0.8600
Se3—C3	1.86 (2)	N12—H12B	0.8600
Se4—C4	1.96 (3)	N28—H28A	0.8600
Se5—C5	1.835 (19)	N28—H28B	0.8600
Se6—C6	1.89 (2)	N28—C8	1.32 (3)
Se7—C7	1.90 (3)	N25—H25A	0.8600
Se8—C8	1.79 (2)	N25—H25B	0.8600
Se9—C9	1.98 (3)	N25—C5	1.42 (2)
C6—N16	1.27 (3)	N17—H17A	0.8600
C6—N26	1.33 (3)	N17—H17B	0.8600
C2—N21	1.26 (4)	N17—C7	1.27 (3)
C2—N22	1.38 (3)	N18—H18A	0.8600
C9—N19	1.18 (4)	N18—H18B	0.8600
C9—N29	1.20 (3)	N18—C8	1.43 (3)
C3—N23	1.32 (3)	N23—H23A	0.8600
C3—N13	1.34 (3)	N23—H23B	0.8600
C1—N11	1.32 (3)	N14—H14A	0.8600
C1—N12	1.31 (3)	N14—H14B	0.8600
N16—H16A	0.8600	N14—C4	1.26 (3)
N16—H16B	0.8600	N24—H24A	0.8600
N21—H21A	0.8600	N24—H24B	0.8600
N21—H21B	0.8600	N24—C4	1.20 (3)
N19—H19A	0.8600	N27—H27A	0.8600
N19—H19B	0.8600	N27—H27B	0.8600
N29—H29A	0.8600	N27—C7	1.27 (3)
N29—H29B	0.8600	N13—H13A	0.8600
N22—H22A	0.8600	N13—H13B	0.8600
N22—H22B	0.8600	C5—N15	1.30 (3)
N26—H26A	0.8600	N15—H15A	0.8600
N26—H26B	0.8600	N15—H15B	0.8600
N11—H11A	0.8600
N16—C6—Se6	122.7 (16)	C8—N28—H28B	120.0
N16—C6—N26	121 (2)	H25A—N25—H25B	120.0
N26—C6—Se6	115.9 (16)	C5—N25—H25A	120.0
N21—C2—Se2	125 (2)	C5—N25—H25B	120.0
N21—C2—N22	118 (3)	H17A—N17—H17B	120.0
N22—C2—Se2	117 (2)	C7—N17—H17A	120.0
N19—C9—Se9	116 (2)	C7—N17—H17B	120.0
N19—C9—N29	127 (3)	H18A—N18—H18B	120.0
N29—C9—Se9	115 (3)	C8—N18—H18A	120.0
N23—C3—Se3	121.5 (17)	C8—N18—H18B	120.0
N23—C3—N13	116 (2)	C3—N23—H23A	120.0
N13—C3—Se3	122.6 (17)	C3—N23—H23B	120.0
N11—C1—Se1	118.4 (19)	H23A—N23—H23B	120.0
N12—C1—Se1	121.0 (15)	H14A—N14—H14B	120.0
N12—C1—N11	120 (2)	C4—N14—H14A	120.0
C6—N16—H16A	120.0	C4—N14—H14B	120.0
C6—N16—H16B	120.0	H24A—N24—H24B	120.0
H16A—N16—H16B	120.0	C4—N24—H24A	120.0
C2—N21—H21A	120.0	C4—N24—H24B	120.0
C2—N21—H21B	120.0	H27A—N27—H27B	120.0
H21A—N21—H21B	120.0	C7—N27—H27A	120.0
C9—N19—H19A	120.0	C7—N27—H27B	120.0
C9—N19—H19B	120.0	C3—N13—H13A	120.0
H19A—N19—H19B	120.0	C3—N13—H13B	120.0
C9—N29—H29A	120.0	H13A—N13—H13B	120.0
C9—N29—H29B	120.0	N17—C7—Se7	120 (2)
H29A—N29—H29B	120.0	N17—C7—N27	119 (3)
C2—N22—H22A	120.0	N27—C7—Se7	121 (2)
C2—N22—H22B	120.0	N25—C5—Se5	117.6 (15)
H22A—N22—H22B	120.0	N15—C5—Se5	126.4 (16)
C6—N26—H26A	120.0	N15—C5—N25	115.5 (19)
C6—N26—H26B	120.0	N28—C8—Se8	127 (2)
H26A—N26—H26B	120.0	N28—C8—N18	114 (2)
C1—N11—H11A	120.0	N18—C8—Se8	119.8 (19)
C1—N11—H11B	120.0	N14—C4—Se4	114 (2)
H11A—N11—H11B	120.0	N24—C4—Se4	117 (2)
C1—N12—H12A	120.0	N24—C4—N14	129 (4)
C1—N12—H12B	120.0	C5—N15—H15A	120.0
H12A—N12—H12B	120.0	C5—N15—H15B	120.0
H28A—N28—H28B	120.0	H15A—N15—H15B	120.0
C8—N28—H28A	120.0

Selenourea (phase_alpha_Selenourea_303K)

Crystal data

CH4N2Se	Dx = 2.094 Mg m^−3
Mr = 123.02	Cu Kα radiation, λ = 1.54184 Å
Trigonal, P31	Cell parameters from 7386 reflections
a = 15.2813 (2) Å	θ = 3.3–72.1°
c = 13.0272 (2) Å	µ = 11.21 mm^−1
V = 2634.52 (8) Å^3	T = 303 K
Z = 27	Plate, orange
F(000) = 1566	0.25 × 0.10 × 0.05 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	3791 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	3754 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.033
Detector resolution: 10.5384 pixels mm^-1	θmax = 72.2°, θmin = 3.3°
ω scans	h = −16→15
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −14→18
Tmin = 0.240, Tmax = 1.000	l = −11→15
7938 measured reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0478P)^2 + 0.205P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.027	(Δ/σ)max = 0.001
wR(F^2) = 0.075	Δρmax = 0.40 e Å^−3
S = 1.07	Δρmin = −0.39 e Å^−3
3791 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
326 parameters	Extinction coefficient: 0.00070 (4)
1 restraint	Absolute structure: Classical Flack method preferred over Parsons because s.u. lower.
Primary atom site location: dual	Absolute structure parameter: 0.00 (5)
Hydrogen site location: inferred from neighbouring sites

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component perfect inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	0.30604 (5)	0.35121 (5)	0.09707 (4)	0.03728 (17)
Se2	0.39423 (5)	0.36028 (6)	0.75801 (4)	0.03868 (18)
Se3	0.30511 (5)	0.27099 (5)	0.42668 (5)	0.03677 (17)
Se4	0.63095 (6)	0.60745 (5)	0.70716 (4)	0.03992 (19)
Se5	0.72119 (5)	0.69323 (5)	0.05051 (5)	0.03714 (17)
Se6	0.63403 (5)	0.70198 (6)	0.38293 (4)	0.03698 (17)
Se7	0.72897 (5)	0.37623 (6)	0.47290 (6)	0.0502 (2)
Se8	0.29803 (5)	0.70017 (5)	0.66503 (6)	0.0428 (2)
Se9	1.06999 (5)	1.02926 (6)	0.46099 (7)	0.0499 (2)
C6	0.7469 (5)	0.6862 (5)	0.3912 (5)	0.0411 (14)
C2	0.2569 (5)	0.3160 (5)	0.7567 (5)	0.0442 (16)
C9	0.9356 (5)	0.9955 (5)	0.4554 (5)	0.0469 (16)
C3	0.4115 (5)	0.4038 (5)	0.4176 (5)	0.0477 (17)
C1	0.3863 (5)	0.2907 (5)	0.0951 (4)	0.0382 (15)
N16	0.8029 (4)	0.6983 (5)	0.3093 (4)	0.0532 (15)
H16A	0.855258	0.691362	0.314235	0.064*
H16B	0.787036	0.713074	0.251124	0.064*
N21	0.2082 (4)	0.3136 (5)	0.8413 (4)	0.0584 (17)
H21A	0.144780	0.293868	0.838921	0.070*
H21B	0.239973	0.331806	0.898873	0.070*
N19	0.8897 (5)	1.0067 (5)	0.5369 (4)	0.0656 (19)
H19A	0.828124	0.993615	0.532225	0.079*
H19B	0.921491	1.027127	0.594185	0.079*
N29	0.8837 (5)	0.9645 (6)	0.3710 (5)	0.080 (2)
H29A	0.822288	0.952151	0.369505	0.096*
H29B	0.910719	0.956254	0.316684	0.096*
N22	0.2063 (5)	0.2879 (8)	0.6709 (5)	0.109 (4)
H22A	0.142897	0.268404	0.670384	0.130*
H22B	0.236385	0.288752	0.614744	0.130*
N26	0.7742 (5)	0.6635 (6)	0.4792 (4)	0.074 (2)
H26A	0.826953	0.657022	0.481706	0.089*
H26B	0.739225	0.655129	0.533743	0.089*
N11	0.4347 (4)	0.2923 (5)	0.0105 (4)	0.0520 (15)
H11A	0.469532	0.262299	0.008910	0.062*
H11B	0.431334	0.323469	−0.043077	0.062*
N12	0.3924 (5)	0.2426 (5)	0.1763 (4)	0.0652 (19)
H12A	0.427494	0.212865	0.173698	0.078*
H12B	0.361227	0.240958	0.231872	0.078*
N28	0.3863 (6)	0.5973 (6)	0.7520 (5)	0.080 (2)
H28A	0.421085	0.567161	0.750739	0.096*
H28B	0.357041	0.598851	0.807800	0.096*
N25	0.5278 (4)	0.6266 (5)	0.1270 (4)	0.0575 (17)
H25A	0.462905	0.595206	0.124344	0.069*
H25B	0.558514	0.659006	0.181691	0.069*
N17	0.5424 (5)	0.2433 (5)	0.3861 (5)	0.0674 (19)
H17A	0.478163	0.202696	0.386416	0.081*
H17B	0.575614	0.256197	0.329474	0.081*
N18	0.4252 (6)	0.6362 (7)	0.5837 (5)	0.100 (3)
H18A	0.459186	0.605284	0.585913	0.120*
H18B	0.421695	0.663798	0.527514	0.120*
N23	0.4716 (5)	0.4480 (5)	0.4966 (4)	0.0661 (18)
H23A	0.522039	0.508318	0.490587	0.079*
H23B	0.460314	0.416497	0.554063	0.079*
N14	0.6792 (6)	0.7995 (5)	0.6442 (5)	0.084 (2)
H14A	0.705207	0.863819	0.650847	0.101*
H14B	0.646379	0.769913	0.589367	0.101*
N24	0.7394 (5)	0.7934 (4)	0.8000 (5)	0.070 (2)
H24A	0.764946	0.857731	0.805371	0.084*
H24B	0.746803	0.759910	0.848919	0.084*
N27	0.5366 (5)	0.2640 (6)	0.5568 (5)	0.080 (2)
H27A	0.472406	0.223181	0.554912	0.096*
H27B	0.565628	0.290641	0.614137	0.096*
N13	0.4313 (6)	0.4542 (5)	0.3319 (5)	0.094 (3)
H13A	0.482246	0.514399	0.328134	0.112*
H13B	0.393316	0.427177	0.279174	0.112*
C7	0.5900 (5)	0.2858 (5)	0.4724 (5)	0.0473 (16)
C5	0.5807 (5)	0.6251 (5)	0.0467 (5)	0.0398 (14)
C8	0.3778 (6)	0.6415 (6)	0.6678 (5)	0.0540 (18)
C4	0.6894 (6)	0.7467 (5)	0.7177 (5)	0.0467 (17)
N15	0.5312 (4)	0.5745 (5)	−0.0363 (4)	0.0659 (19)
H15A	0.466256	0.543610	−0.037357	0.079*
H15B	0.563990	0.572559	−0.089035	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0388 (4)	0.0388 (4)	0.0380 (3)	0.0222 (3)	−0.0006 (3)	0.0003 (3)
Se2	0.0325 (4)	0.0428 (4)	0.0397 (4)	0.0180 (3)	0.0006 (3)	0.0040 (3)
Se3	0.0383 (4)	0.0314 (4)	0.0384 (3)	0.0158 (3)	0.0008 (3)	0.0006 (3)
Se4	0.0414 (4)	0.0330 (4)	0.0413 (4)	0.0155 (3)	0.0000 (3)	0.0002 (3)
Se5	0.0328 (4)	0.0379 (4)	0.0403 (3)	0.0173 (3)	−0.0019 (3)	−0.0007 (3)
Se6	0.0359 (4)	0.0393 (4)	0.0396 (4)	0.0217 (3)	−0.0010 (3)	0.0001 (3)
Se7	0.0362 (4)	0.0458 (4)	0.0500 (5)	0.0066 (3)	−0.0027 (3)	0.0006 (3)
Se8	0.0521 (5)	0.0429 (4)	0.0424 (4)	0.0304 (4)	−0.0026 (3)	−0.0017 (3)
Se9	0.0358 (4)	0.0588 (5)	0.0552 (4)	0.0237 (4)	0.0047 (3)	0.0122 (4)
C6	0.040 (4)	0.043 (4)	0.045 (3)	0.025 (3)	−0.002 (3)	−0.004 (3)
C2	0.036 (4)	0.060 (5)	0.040 (3)	0.026 (3)	−0.002 (3)	−0.002 (3)
C9	0.043 (4)	0.047 (4)	0.051 (4)	0.022 (3)	−0.001 (3)	0.002 (3)
C3	0.058 (4)	0.040 (4)	0.035 (3)	0.017 (3)	0.001 (3)	−0.003 (3)
C1	0.042 (4)	0.044 (4)	0.031 (3)	0.023 (3)	−0.001 (2)	−0.004 (3)
N16	0.044 (3)	0.077 (4)	0.047 (3)	0.037 (3)	0.005 (3)	0.006 (3)
N21	0.043 (3)	0.100 (5)	0.034 (3)	0.037 (4)	0.002 (2)	−0.005 (3)
N19	0.055 (4)	0.113 (6)	0.046 (3)	0.056 (4)	−0.001 (3)	−0.007 (3)
N29	0.045 (4)	0.130 (7)	0.056 (4)	0.036 (4)	−0.005 (3)	−0.027 (4)
N22	0.051 (4)	0.243 (11)	0.041 (4)	0.079 (6)	−0.012 (3)	−0.023 (5)
N26	0.078 (5)	0.141 (7)	0.044 (3)	0.085 (5)	0.002 (3)	0.012 (4)
N11	0.060 (4)	0.069 (4)	0.043 (3)	0.045 (3)	0.009 (3)	0.007 (3)
N12	0.093 (5)	0.103 (5)	0.041 (3)	0.081 (5)	0.011 (3)	0.016 (3)
N28	0.117 (6)	0.124 (7)	0.050 (4)	0.099 (6)	0.020 (4)	0.028 (4)
N25	0.042 (3)	0.077 (4)	0.041 (3)	0.021 (3)	0.006 (3)	−0.009 (3)
N17	0.040 (3)	0.077 (5)	0.056 (4)	0.007 (3)	−0.002 (3)	−0.010 (3)
N18	0.121 (7)	0.204 (9)	0.048 (4)	0.137 (7)	0.021 (4)	0.024 (5)
N23	0.062 (4)	0.056 (4)	0.047 (3)	0.004 (3)	−0.009 (3)	−0.002 (3)
N14	0.156 (8)	0.043 (4)	0.053 (4)	0.050 (4)	−0.023 (4)	−0.002 (3)
N24	0.108 (6)	0.032 (3)	0.053 (4)	0.022 (3)	−0.013 (4)	−0.004 (3)
N27	0.038 (4)	0.115 (6)	0.060 (4)	0.018 (4)	0.001 (3)	−0.002 (4)
N13	0.123 (7)	0.044 (4)	0.050 (4)	−0.005 (4)	−0.014 (4)	0.007 (3)
C7	0.037 (4)	0.045 (4)	0.054 (4)	0.016 (3)	−0.003 (3)	−0.002 (3)
C5	0.036 (3)	0.045 (4)	0.035 (3)	0.017 (3)	−0.003 (3)	0.002 (3)
C8	0.059 (5)	0.076 (5)	0.043 (4)	0.046 (4)	0.005 (3)	0.007 (3)
C4	0.053 (4)	0.045 (4)	0.042 (4)	0.024 (3)	0.004 (3)	0.002 (3)
N15	0.037 (3)	0.092 (5)	0.046 (3)	0.015 (3)	−0.006 (3)	−0.014 (3)

Geometric parameters (Å, º)

Se1—C1	1.869 (6)	N11—H11B	0.8600
Se2—C2	1.855 (7)	N12—H12A	0.8600
Se3—C3	1.865 (7)	N12—H12B	0.8600
Se4—C4	1.856 (7)	N28—H28A	0.8600
Se5—C5	1.860 (6)	N28—H28B	0.8600
Se6—C6	1.860 (6)	N28—C8	1.328 (9)
Se7—C7	1.866 (7)	N25—H25A	0.8600
Se8—C8	1.840 (7)	N25—H25B	0.8600
Se9—C9	1.852 (7)	N25—C5	1.330 (8)
C6—N16	1.322 (8)	N17—H17A	0.8600
C6—N26	1.324 (8)	N17—H17B	0.8600
C2—N21	1.320 (8)	N17—C7	1.320 (9)
C2—N22	1.304 (8)	N18—H18A	0.8600
C9—N19	1.330 (8)	N18—H18B	0.8600
C9—N29	1.299 (9)	N18—C8	1.337 (9)
C3—N23	1.318 (8)	N23—H23A	0.8600
C3—N13	1.302 (8)	N23—H23B	0.8600
C1—N11	1.320 (8)	N14—H14A	0.8600
C1—N12	1.318 (8)	N14—H14B	0.8600
N16—H16A	0.8600	N14—C4	1.311 (9)
N16—H16B	0.8600	N24—H24A	0.8600
N21—H21A	0.8600	N24—H24B	0.8600
N21—H21B	0.8600	N24—C4	1.302 (9)
N19—H19A	0.8600	N27—H27A	0.8600
N19—H19B	0.8600	N27—H27B	0.8600
N29—H29A	0.8600	N27—C7	1.310 (9)
N29—H29B	0.8600	N13—H13A	0.8600
N22—H22A	0.8600	N13—H13B	0.8600
N22—H22B	0.8600	C5—N15	1.324 (8)
N26—H26A	0.8600	N15—H15A	0.8600
N26—H26B	0.8600	N15—H15B	0.8600
N11—H11A	0.8600
N16—C6—Se6	120.9 (5)	C8—N28—H28B	120.0
N16—C6—N26	117.9 (6)	H25A—N25—H25B	120.0
N26—C6—Se6	121.3 (5)	C5—N25—H25A	120.0
N21—C2—Se2	121.4 (5)	C5—N25—H25B	120.0
N22—C2—Se2	120.3 (5)	H17A—N17—H17B	120.0
N22—C2—N21	118.3 (6)	C7—N17—H17A	120.0
N19—C9—Se9	121.1 (5)	C7—N17—H17B	120.0
N29—C9—Se9	121.7 (5)	H18A—N18—H18B	120.0
N29—C9—N19	117.2 (6)	C8—N18—H18A	120.0
N23—C3—Se3	120.9 (5)	C8—N18—H18B	120.0
N13—C3—Se3	121.1 (5)	C3—N23—H23A	120.0
N13—C3—N23	118.0 (6)	C3—N23—H23B	120.0
N11—C1—Se1	120.1 (5)	H23A—N23—H23B	120.0
N12—C1—Se1	120.8 (5)	H14A—N14—H14B	120.0
N12—C1—N11	119.1 (6)	C4—N14—H14A	120.0
C6—N16—H16A	120.0	C4—N14—H14B	120.0
C6—N16—H16B	120.0	H24A—N24—H24B	120.0
H16A—N16—H16B	120.0	C4—N24—H24A	120.0
C2—N21—H21A	120.0	C4—N24—H24B	120.0
C2—N21—H21B	120.0	H27A—N27—H27B	120.0
H21A—N21—H21B	120.0	C7—N27—H27A	120.0
C9—N19—H19A	120.0	C7—N27—H27B	120.0
C9—N19—H19B	120.0	C3—N13—H13A	120.0
H19A—N19—H19B	120.0	C3—N13—H13B	120.0
C9—N29—H29A	120.0	H13A—N13—H13B	120.0
C9—N29—H29B	120.0	N17—C7—Se7	120.7 (5)
H29A—N29—H29B	120.0	N27—C7—Se7	121.3 (5)
C2—N22—H22A	120.0	N27—C7—N17	118.0 (6)
C2—N22—H22B	120.0	N25—C5—Se5	120.7 (5)
H22A—N22—H22B	120.0	N15—C5—Se5	120.7 (5)
C6—N26—H26A	120.0	N15—C5—N25	118.5 (6)
C6—N26—H26B	120.0	N28—C8—Se8	121.4 (5)
H26A—N26—H26B	120.0	N28—C8—N18	116.9 (7)
C1—N11—H11A	120.0	N18—C8—Se8	121.6 (5)
C1—N11—H11B	120.0	N14—C4—Se4	121.0 (5)
H11A—N11—H11B	120.0	N24—C4—Se4	120.2 (5)
C1—N12—H12A	120.0	N24—C4—N14	118.8 (7)
C1—N12—H12B	120.0	C5—N15—H15A	120.0
H12A—N12—H12B	120.0	C5—N15—H15B	120.0
H28A—N28—H28B	120.0	H15A—N15—H15B	120.0
C8—N28—H28A	120.0

Selenourea (phase_alpha_Selenourea_313K)

Crystal data

CH4N2Se	Dx = 2.089 Mg m^−3
Mr = 123.02	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P31	Cell parameters from 3411 reflections
a = 15.2940 (5) Å	θ = 3.5–26.4°
c = 13.0350 (4) Å	µ = 9.37 mm^−1
V = 2640.48 (19) Å^3	T = 313 K
Z = 27	Plate, orange
F(000) = 1566	0.25 × 0.10 × 0.05 mm

Data collection

Xcalibur, Eos diffractometer	8231 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	5822 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 16.1544 pixels mm^-1	θmax = 29.0°, θmin = 3.1°
ω scans	h = −20→20
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −19→19
Tmin = 0.338, Tmax = 0.626	l = −17→17
28408 measured reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + 46.5028P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.081	(Δ/σ)max < 0.001
wR(F^2) = 0.144	Δρmax = 1.74 e Å^−3
S = 1.08	Δρmin = −1.92 e Å^−3
8231 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
326 parameters	Extinction coefficient: 0.00066 (4)
50 restraints	Absolute structure: Refined as a perfect inversion twin.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.5
Hydrogen site location: inferred from neighbouring sites

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component perfect inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	0.30575 (18)	0.35152 (18)	0.09653 (16)	0.0364 (5)
Se2	0.39364 (19)	0.36082 (19)	0.75568 (17)	0.0383 (6)
Se3	0.30445 (18)	0.27075 (17)	0.42849 (18)	0.0357 (5)
Se4	0.6315 (2)	0.6085 (2)	0.70793 (17)	0.0431 (7)
Se5	0.72106 (18)	0.69334 (19)	0.04976 (19)	0.0391 (6)
Se6	0.63415 (18)	0.70144 (19)	0.38296 (16)	0.0344 (5)
Se7	0.73130 (19)	0.3741 (2)	0.46978 (19)	0.0514 (8)
Se8	0.29963 (19)	0.70130 (18)	0.6658 (2)	0.0430 (6)
Se9	1.06951 (19)	1.0313 (2)	0.4656 (2)	0.0530 (7)
C6	0.7462 (15)	0.6804 (16)	0.3873 (17)	0.038 (5)
C2	0.257 (3)	0.319 (3)	0.763 (2)	0.085 (12)
C9	0.927 (2)	0.9906 (15)	0.462 (2)	0.057 (7)
C3	0.4123 (18)	0.4009 (17)	0.4179 (17)	0.045 (5)
C1	0.3836 (18)	0.2889 (19)	0.0948 (15)	0.041 (6)
N16	0.8019 (13)	0.6924 (16)	0.3086 (14)	0.049 (5)
H16A	0.852961	0.683517	0.314098	0.059*
H16B	0.788028	0.709191	0.250443	0.059*
N21	0.2082 (19)	0.3108 (19)	0.8405 (18)	0.076 (7)
H21A	0.143795	0.285162	0.836711	0.092*
H21B	0.238224	0.330526	0.898738	0.092*
N19	0.8872 (18)	0.996 (2)	0.5380 (19)	0.090 (9)
H19A	0.825840	0.983323	0.535739	0.108*
H19B	0.919498	1.011926	0.595276	0.108*
N29	0.8860 (18)	0.9683 (18)	0.3800 (18)	0.075 (7)
H29A	0.824658	0.955301	0.374174	0.090*
H29B	0.918044	0.965502	0.327045	0.090*
N22	0.206 (3)	0.286 (3)	0.667 (3)	0.122 (11)
H22A	0.141299	0.260574	0.664009	0.146*
H22B	0.239229	0.291695	0.611870	0.146*
N26	0.7657 (17)	0.655 (2)	0.4775 (14)	0.071 (7)
H26A	0.816518	0.645452	0.484394	0.085*
H26B	0.727711	0.646961	0.529272	0.085*
N11	0.4324 (13)	0.2923 (14)	0.0086 (12)	0.041 (4)
H11A	0.467080	0.262166	0.005562	0.049*
H11B	0.429119	0.324572	−0.043957	0.049*
N12	0.3895 (18)	0.2403 (19)	0.1722 (13)	0.070 (7)
H12A	0.424476	0.210584	0.168093	0.084*
H12B	0.358489	0.237522	0.228244	0.084*
N28	0.394 (2)	0.605 (2)	0.7554 (14)	0.080 (2)
H28A	0.439092	0.587551	0.753490	0.096*
H28B	0.362935	0.601009	0.811918	0.096*
N25	0.5284 (13)	0.6225 (15)	0.1298 (14)	0.053 (5)
H25A	0.463765	0.594955	0.127502	0.064*
H25B	0.560347	0.650719	0.185387	0.064*
N17	0.5430 (14)	0.2477 (16)	0.3900 (17)	0.072 (8)
H17A	0.478137	0.214211	0.388550	0.086*
H17B	0.576930	0.254391	0.335028	0.086*
N18	0.4273 (18)	0.642 (2)	0.5838 (18)	0.077 (7)
H18A	0.471736	0.623437	0.586866	0.092*
H18B	0.416415	0.663375	0.526800	0.092*
N23	0.4735 (16)	0.4472 (17)	0.4967 (16)	0.071 (7)
H23A	0.521628	0.508636	0.490525	0.085*
H23B	0.464826	0.415759	0.553805	0.085*
N14	0.680 (2)	0.799 (2)	0.643 (2)	0.114 (10)
H14A	0.707221	0.863950	0.643007	0.137*
H14B	0.644197	0.764890	0.591272	0.137*
N24	0.742 (2)	0.794 (2)	0.800 (2)	0.098 (9)
H24A	0.772529	0.858302	0.808096	0.118*
H24B	0.745691	0.756458	0.847477	0.118*
N27	0.542 (2)	0.279 (2)	0.556 (2)	0.092 (8)
H27A	0.476638	0.246100	0.557501	0.110*
H27B	0.574767	0.306751	0.611645	0.110*
N13	0.431 (2)	0.4557 (19)	0.3309 (18)	0.084 (7)
H13A	0.480291	0.516891	0.328846	0.100*
H13B	0.393745	0.429260	0.277696	0.100*
C7	0.589 (2)	0.287 (3)	0.4730 (18)	0.0473 (16)
C5	0.5821 (14)	0.6215 (16)	0.0423 (14)	0.030 (4)
C8	0.372 (2)	0.638 (3)	0.6729 (19)	0.073 (9)
C4	0.692 (2)	0.754 (3)	0.7195 (17)	0.069 (10)
N15	0.5296 (15)	0.5784 (17)	−0.0369 (15)	0.066 (7)
H15A	0.465089	0.551999	−0.035069	0.079*
H15B	0.558708	0.575721	−0.092301	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0398 (13)	0.0358 (12)	0.0356 (11)	0.0204 (11)	−0.0043 (9)	0.0021 (10)
Se2	0.0335 (13)	0.0410 (13)	0.0410 (13)	0.0189 (11)	−0.0041 (10)	−0.0012 (10)
Se3	0.0368 (13)	0.0303 (11)	0.0339 (10)	0.0122 (10)	0.0023 (9)	0.0000 (10)
Se4	0.0441 (14)	0.0394 (14)	0.0429 (15)	0.0188 (12)	−0.0040 (10)	−0.0024 (10)
Se5	0.0342 (12)	0.0427 (13)	0.0425 (12)	0.0207 (11)	0.0039 (10)	0.0059 (10)
Se6	0.0366 (12)	0.0386 (12)	0.0356 (12)	0.0246 (10)	0.0001 (9)	−0.0018 (9)
Se7	0.0367 (14)	0.0453 (15)	0.0500 (16)	0.0039 (11)	0.0023 (11)	0.0083 (11)
Se8	0.0541 (15)	0.0426 (14)	0.0430 (14)	0.0321 (12)	−0.0076 (11)	−0.0046 (10)
Se9	0.0403 (14)	0.0562 (17)	0.0569 (16)	0.0201 (13)	−0.0014 (12)	0.0061 (12)
C6	0.029 (10)	0.043 (12)	0.050 (13)	0.023 (10)	0.001 (9)	0.001 (10)
C2	0.15 (3)	0.12 (3)	0.045 (15)	0.11 (3)	−0.041 (19)	−0.048 (17)
C9	0.09 (2)	0.046 (14)	0.049 (15)	0.042 (15)	−0.020 (14)	0.006 (12)
C3	0.051 (14)	0.041 (13)	0.036 (11)	0.016 (11)	0.005 (10)	0.008 (10)
C1	0.043 (13)	0.065 (16)	0.022 (10)	0.032 (12)	0.015 (8)	−0.001 (10)
N16	0.034 (10)	0.093 (16)	0.045 (10)	0.049 (11)	−0.001 (8)	−0.005 (10)
N21	0.064 (10)	0.099 (12)	0.063 (10)	0.038 (8)	0.001 (8)	−0.003 (9)
N19	0.068 (16)	0.16 (3)	0.062 (15)	0.073 (19)	−0.017 (12)	−0.041 (17)
N29	0.058 (10)	0.090 (11)	0.066 (11)	0.028 (8)	−0.018 (8)	−0.004 (8)
N22	0.111 (14)	0.141 (15)	0.116 (15)	0.065 (11)	0.000 (10)	−0.003 (10)
N26	0.089 (16)	0.15 (2)	0.037 (10)	0.105 (18)	0.006 (10)	0.018 (13)
N11	0.052 (11)	0.062 (12)	0.022 (8)	0.039 (10)	0.001 (8)	0.007 (8)
N12	0.104 (18)	0.14 (2)	0.019 (9)	0.102 (18)	0.020 (10)	0.024 (11)
N28	0.117 (6)	0.124 (7)	0.050 (4)	0.098 (6)	0.020 (4)	0.028 (4)
N25	0.022 (9)	0.077 (15)	0.046 (11)	0.014 (9)	0.014 (8)	−0.014 (10)
N17	0.023 (10)	0.077 (16)	0.059 (14)	−0.019 (10)	0.009 (9)	−0.034 (11)
N18	0.078 (10)	0.106 (11)	0.071 (11)	0.064 (9)	0.002 (8)	0.009 (8)
N23	0.063 (15)	0.061 (14)	0.047 (12)	0.000 (12)	0.002 (11)	−0.013 (10)
N14	0.128 (14)	0.097 (13)	0.103 (13)	0.046 (10)	−0.009 (10)	−0.002 (10)
N24	0.107 (13)	0.093 (12)	0.091 (12)	0.046 (9)	−0.006 (9)	0.008 (9)
N27	0.077 (11)	0.108 (13)	0.080 (12)	0.039 (9)	−0.003 (9)	0.004 (9)
N13	0.090 (11)	0.065 (10)	0.064 (10)	0.014 (8)	−0.002 (9)	0.002 (8)
C7	0.038 (4)	0.045 (4)	0.054 (4)	0.017 (3)	−0.003 (3)	−0.002 (3)
C5	0.025 (9)	0.048 (12)	0.023 (9)	0.022 (9)	0.007 (7)	0.002 (8)
C8	0.11 (2)	0.14 (3)	0.037 (13)	0.11 (2)	0.005 (14)	0.005 (15)
C4	0.08 (2)	0.14 (3)	0.022 (12)	0.08 (2)	−0.016 (12)	−0.011 (14)
N15	0.042 (12)	0.081 (16)	0.048 (12)	0.010 (11)	−0.008 (9)	−0.035 (11)

Geometric parameters (Å, º)

Se1—C1	1.86 (2)	N11—H11B	0.8600
Se2—C2	1.86 (4)	N12—H12A	0.8600
Se3—C3	1.85 (2)	N12—H12B	0.8600
Se4—C4	1.94 (4)	N28—H28A	0.8600
Se5—C5	1.844 (19)	N28—H28B	0.8600
Se6—C6	1.89 (2)	N28—C8	1.30 (3)
Se7—C7	1.91 (3)	N25—H25A	0.8600
Se8—C8	1.80 (2)	N25—H25B	0.8600
Se9—C9	1.94 (3)	N25—C5	1.41 (2)
C6—N16	1.29 (3)	N17—H17A	0.8600
C6—N26	1.32 (3)	N17—H17B	0.8600
C2—N21	1.23 (4)	N17—C7	1.26 (3)
C2—N22	1.43 (4)	N18—H18A	0.8600
C9—N19	1.18 (3)	N18—H18B	0.8600
C9—N29	1.21 (3)	N18—C8	1.42 (3)
C3—N23	1.33 (3)	N23—H23A	0.8600
C3—N13	1.35 (3)	N23—H23B	0.8600
C1—N11	1.34 (2)	N14—H14A	0.8600
C1—N12	1.28 (3)	N14—H14B	0.8600
N16—H16A	0.8600	N14—C4	1.28 (4)
N16—H16B	0.8600	N24—H24A	0.8600
N21—H21A	0.8600	N24—H24B	0.8600
N21—H21B	0.8600	N24—C4	1.26 (3)
N19—H19A	0.8600	N27—H27A	0.8600
N19—H19B	0.8600	N27—H27B	0.8600
N29—H29A	0.8600	N27—C7	1.28 (3)
N29—H29B	0.8600	N13—H13A	0.8600
N22—H22A	0.8600	N13—H13B	0.8600
N22—H22B	0.8600	C5—N15	1.27 (3)
N26—H26A	0.8600	N15—H15A	0.8600
N26—H26B	0.8600	N15—H15B	0.8600
N11—H11A	0.8600
N16—C6—Se6	122.9 (16)	C8—N28—H28B	120.0
N16—C6—N26	121.2 (19)	H25A—N25—H25B	120.0
N26—C6—Se6	115.9 (16)	C5—N25—H25A	120.0
N21—C2—Se2	127 (2)	C5—N25—H25B	120.0
N21—C2—N22	119 (3)	H17A—N17—H17B	120.0
N22—C2—Se2	114 (2)	C7—N17—H17A	120.0
N19—C9—Se9	120 (2)	C7—N17—H17B	120.0
N19—C9—N29	123 (3)	H18A—N18—H18B	120.0
N29—C9—Se9	117 (2)	C8—N18—H18A	120.0
N23—C3—Se3	121.8 (17)	C8—N18—H18B	120.0
N23—C3—N13	116 (2)	C3—N23—H23A	120.0
N13—C3—Se3	121.9 (19)	C3—N23—H23B	120.0
N11—C1—Se1	118.6 (16)	H23A—N23—H23B	120.0
N12—C1—Se1	122.4 (15)	H14A—N14—H14B	120.0
N12—C1—N11	119 (2)	C4—N14—H14A	120.0
C6—N16—H16A	120.0	C4—N14—H14B	120.0
C6—N16—H16B	120.0	H24A—N24—H24B	120.0
H16A—N16—H16B	120.0	C4—N24—H24A	120.0
C2—N21—H21A	120.0	C4—N24—H24B	120.0
C2—N21—H21B	120.0	H27A—N27—H27B	120.0
H21A—N21—H21B	120.0	C7—N27—H27A	120.0
C9—N19—H19A	120.0	C7—N27—H27B	120.0
C9—N19—H19B	120.0	C3—N13—H13A	120.0
H19A—N19—H19B	120.0	C3—N13—H13B	120.0
C9—N29—H29A	120.0	H13A—N13—H13B	120.0
C9—N29—H29B	120.0	N17—C7—Se7	118.7 (19)
H29A—N29—H29B	120.0	N17—C7—N27	122 (3)
C2—N22—H22A	120.0	N27—C7—Se7	119 (2)
C2—N22—H22B	120.0	N25—C5—Se5	117.1 (14)
H22A—N22—H22B	120.0	N15—C5—Se5	126.3 (15)
C6—N26—H26A	120.0	N15—C5—N25	116.3 (18)
C6—N26—H26B	120.0	N28—C8—Se8	126.6 (19)
H26A—N26—H26B	120.0	N28—C8—N18	116 (2)
C1—N11—H11A	120.0	N18—C8—Se8	116.6 (19)
C1—N11—H11B	120.0	N14—C4—Se4	116 (2)
H11A—N11—H11B	120.0	N24—C4—Se4	116 (2)
C1—N12—H12A	120.0	N24—C4—N14	127 (4)
C1—N12—H12B	120.0	C5—N15—H15A	120.0
H12A—N12—H12B	120.0	C5—N15—H15B	120.0
H28A—N28—H28B	120.0	H15A—N15—H15B	120.0
C8—N28—H28A	120.0

Selenourea (phase_alpha_Selenourea_323K)

Crystal data

CH4N2Se	Dx = 2.090 Mg m^−3
Mr = 123.02	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P31	Cell parameters from 3345 reflections
a = 15.3052 (6) Å	θ = 4.1–26.3°
c = 13.0398 (4) Å	µ = 9.38 mm^−1
V = 2645.33 (2) Å^3	T = 323 K
Z = 27	Plate, orange
F(000) = 1566	0.25 × 0.10 × 0.05 mm

Data collection

Xcalibur, Eos diffractometer	8247 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	5710 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 16.1544 pixels mm^-1	θmax = 29.0°, θmin = 3.1°
ω scans	h = −19→19
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −20→20
Tmin = 0.338, Tmax = 0.626	l = −17→17
28481 measured reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + 85.4123P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.098	(Δ/σ)max < 0.001
wR(F^2) = 0.179	Δρmax = 0.74 e Å^−3
S = 1.05	Δρmin = −1.92 e Å^−3
8247 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
326 parameters	Extinction coefficient: 0.00066 (4)
107 restraints	Absolute structure: Refined as a perfect inversion twin.
Primary atom site location: dual	Absolute structure parameter: 0.5
Hydrogen site location: inferred from neighbouring sites

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component perfect inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	0.3053 (2)	0.3519 (2)	0.0959 (2)	0.0369 (6)
Se2	0.3930 (2)	0.3607 (2)	0.7550 (2)	0.0387 (7)
Se3	0.3043 (2)	0.2703 (2)	0.4291 (2)	0.0373 (6)
Se4	0.6316 (3)	0.6087 (3)	0.7087 (2)	0.0470 (8)
Se5	0.7210 (2)	0.6931 (3)	0.0485 (3)	0.0443 (7)
Se6	0.6343 (2)	0.7008 (2)	0.38294 (19)	0.0351 (6)
Se7	0.7328 (2)	0.3724 (2)	0.4684 (2)	0.0533 (10)
Se8	0.3002 (2)	0.7020 (2)	0.6669 (3)	0.0457 (8)
Se9	1.0691 (2)	1.0326 (3)	0.4680 (2)	0.0542 (9)
C6	0.7425 (19)	0.674 (2)	0.389 (2)	0.038 (6)
C2	0.256 (3)	0.319 (2)	0.761 (4)	0.093 (13)
C9	0.917 (3)	0.983 (2)	0.464 (2)	0.056 (9)
C3	0.412 (2)	0.400 (2)	0.4197 (19)	0.041 (6)
C1	0.381 (2)	0.289 (2)	0.0974 (19)	0.034 (6)
N16	0.7991 (16)	0.689 (2)	0.3087 (16)	0.079 (11)
H16A	0.851196	0.681831	0.313493	0.095*
H16B	0.784472	0.705965	0.251087	0.095*
N21	0.206 (3)	0.312 (3)	0.840 (3)	0.113 (13)
H21A	0.142304	0.289812	0.835635	0.135*
H21B	0.235608	0.329202	0.898733	0.135*
N19	0.886 (2)	0.989 (2)	0.539 (3)	0.082 (9)
H19A	0.827857	0.985489	0.541292	0.098*
H19B	0.919300	0.997435	0.594562	0.098*
N29	0.887 (2)	0.972 (2)	0.383 (2)	0.069 (8)
H29A	0.829373	0.966839	0.371682	0.083*
H29B	0.921972	0.968730	0.333308	0.083*
N22	0.205 (4)	0.290 (4)	0.663 (4)	0.158 (19)
H22A	0.141314	0.267938	0.659902	0.190*
H22B	0.238604	0.294688	0.608829	0.190*
N26	0.762 (2)	0.649 (3)	0.4763 (17)	0.079 (11)
H26A	0.813905	0.641386	0.482983	0.095*
H26B	0.723729	0.639841	0.528093	0.095*
N11	0.4297 (16)	0.2925 (17)	0.0070 (14)	0.039 (5)
H11A	0.463770	0.261833	0.002515	0.047*
H11B	0.425903	0.325208	−0.044753	0.047*
N12	0.388 (2)	0.241 (2)	0.1705 (16)	0.075 (10)
H12A	0.422651	0.211258	0.164262	0.090*
H12B	0.358562	0.238204	0.227593	0.090*
N28	0.3984 (18)	0.6086 (17)	0.7583 (18)	0.046 (5)
H28A	0.439297	0.585708	0.752943	0.055*
H28B	0.371441	0.607264	0.816587	0.055*
N25	0.5271 (17)	0.6212 (18)	0.1311 (18)	0.050 (6)
H25A	0.462935	0.596663	0.126461	0.060*
H25B	0.557492	0.646514	0.188119	0.060*
N17	0.544 (2)	0.246 (2)	0.397 (2)	0.070 (8)
H17A	0.479835	0.210489	0.400726	0.084*
H17B	0.574819	0.249588	0.340475	0.084*
N18	0.429 (2)	0.643 (2)	0.584 (2)	0.076 (8)
H18A	0.468115	0.617688	0.589457	0.092*
H18B	0.421490	0.664716	0.526317	0.092*
N23	0.475 (2)	0.449 (2)	0.4976 (19)	0.081 (10)
H23A	0.522224	0.510477	0.490060	0.097*
H23B	0.469205	0.418221	0.554787	0.097*
N14	0.676 (3)	0.803 (4)	0.641 (3)	0.135 (16)
H14A	0.702058	0.867051	0.644486	0.162*
H14B	0.640351	0.769851	0.589254	0.162*
N24	0.746 (3)	0.793 (3)	0.802 (3)	0.114 (13)
H24A	0.775357	0.856765	0.812678	0.137*
H24B	0.751955	0.754060	0.845449	0.137*
N27	0.543 (3)	0.286 (3)	0.559 (3)	0.107 (12)
H27A	0.478608	0.249433	0.560653	0.129*
H27B	0.575763	0.317726	0.613195	0.129*
N13	0.430 (3)	0.456 (3)	0.335 (2)	0.092 (10)
H13A	0.478261	0.517588	0.334003	0.110*
H13B	0.392267	0.430748	0.281467	0.110*
C7	0.593 (2)	0.2929 (19)	0.473 (2)	0.049 (7)
C5	0.5829 (15)	0.6199 (16)	0.0443 (16)	0.022 (4)
C8	0.376 (2)	0.648 (2)	0.673 (3)	0.076 (10)
C4	0.693 (3)	0.754 (3)	0.716 (3)	0.085 (13)
N15	0.531 (2)	0.580 (2)	−0.0373 (19)	0.066 (8)
H15A	0.466732	0.557260	−0.036855	0.079*
H15B	0.560029	0.577381	−0.092407	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0425 (17)	0.0332 (14)	0.0357 (13)	0.0194 (13)	−0.0068 (11)	0.0023 (12)
Se2	0.0347 (15)	0.0390 (15)	0.0426 (16)	0.0186 (13)	−0.0074 (12)	−0.0039 (12)
Se3	0.0375 (15)	0.0317 (14)	0.0348 (13)	0.0116 (13)	0.0018 (11)	0.0001 (12)
Se4	0.0482 (18)	0.0455 (19)	0.0443 (19)	0.0212 (15)	−0.0043 (13)	−0.0012 (13)
Se5	0.0395 (16)	0.0482 (17)	0.0478 (16)	0.0239 (14)	0.0082 (13)	0.0122 (13)
Se6	0.0387 (15)	0.0406 (15)	0.0376 (15)	0.0285 (13)	0.0019 (11)	−0.0012 (11)
Se7	0.0370 (17)	0.0479 (18)	0.054 (2)	0.0054 (13)	0.0027 (14)	0.0118 (14)
Se8	0.058 (2)	0.0460 (17)	0.0454 (17)	0.0347 (15)	−0.0084 (14)	−0.0060 (13)
Se9	0.0412 (17)	0.055 (2)	0.057 (2)	0.0164 (15)	−0.0022 (14)	0.0023 (15)
C6	0.031 (13)	0.044 (15)	0.045 (14)	0.024 (12)	0.002 (11)	0.002 (11)
C2	0.094 (14)	0.094 (14)	0.092 (14)	0.048 (8)	0.001 (6)	−0.003 (6)
C9	0.10 (3)	0.032 (14)	0.043 (16)	0.041 (17)	−0.019 (17)	0.000 (12)
C3	0.050 (16)	0.037 (14)	0.028 (12)	0.016 (12)	0.009 (11)	0.008 (10)
C1	0.032 (7)	0.038 (7)	0.031 (7)	0.016 (5)	0.007 (5)	−0.004 (5)
N16	0.11 (2)	0.18 (3)	0.032 (12)	0.13 (3)	0.007 (13)	0.022 (16)
N21	0.112 (13)	0.114 (13)	0.112 (13)	0.056 (7)	0.000 (3)	0.000 (3)
N19	0.079 (12)	0.091 (13)	0.079 (13)	0.045 (10)	−0.005 (9)	−0.013 (10)
N29	0.057 (11)	0.080 (12)	0.064 (11)	0.028 (9)	−0.019 (9)	0.002 (9)
N22	0.158 (19)	0.159 (19)	0.158 (19)	0.080 (10)	0.000 (3)	0.000 (3)
N26	0.11 (2)	0.18 (3)	0.032 (12)	0.13 (3)	0.007 (13)	0.022 (16)
N11	0.045 (13)	0.062 (14)	0.021 (10)	0.034 (12)	0.012 (9)	0.014 (9)
N12	0.13 (3)	0.14 (3)	0.018 (11)	0.11 (2)	0.016 (13)	0.016 (14)
N28	0.057 (10)	0.053 (10)	0.034 (8)	0.033 (8)	0.005 (7)	0.013 (7)
N25	0.035 (9)	0.063 (10)	0.050 (10)	0.022 (8)	0.016 (7)	−0.006 (8)
N17	0.062 (11)	0.064 (11)	0.070 (11)	0.021 (9)	0.004 (9)	−0.013 (9)
N18	0.080 (12)	0.096 (13)	0.074 (12)	0.060 (10)	0.001 (9)	0.010 (9)
N23	0.09 (2)	0.070 (19)	0.034 (13)	0.000 (16)	0.006 (13)	−0.025 (13)
N14	0.145 (19)	0.126 (19)	0.129 (19)	0.063 (12)	−0.004 (11)	0.001 (11)
N24	0.118 (16)	0.114 (16)	0.109 (16)	0.057 (11)	−0.002 (10)	0.005 (10)
N27	0.099 (15)	0.118 (16)	0.098 (15)	0.049 (11)	0.002 (10)	0.006 (10)
N13	0.097 (14)	0.080 (13)	0.074 (13)	0.025 (9)	−0.003 (10)	0.000 (10)
C7	0.049 (8)	0.054 (8)	0.050 (8)	0.030 (6)	−0.002 (5)	−0.003 (5)
C5	0.019 (10)	0.026 (11)	0.023 (10)	0.013 (9)	0.009 (8)	0.001 (8)
C8	0.076 (11)	0.080 (11)	0.077 (12)	0.042 (7)	0.001 (5)	0.001 (5)
C4	0.086 (14)	0.087 (14)	0.085 (14)	0.045 (8)	−0.002 (6)	−0.001 (6)
N15	0.051 (15)	0.081 (19)	0.044 (14)	0.016 (14)	−0.018 (12)	−0.041 (14)

Geometric parameters (Å, º)

Se1—C1	1.84 (3)	N11—H11B	0.8600
Se2—C2	1.87 (4)	N12—H12A	0.8600
Se3—C3	1.84 (3)	N12—H12B	0.8600
Se4—C4	1.94 (5)	N28—H28A	0.8600
Se5—C5	1.83 (2)	N28—H28B	0.8600
Se6—C6	1.89 (2)	N28—C8	1.38 (4)
Se7—C7	1.85 (3)	N25—H25A	0.8600
Se8—C8	1.73 (4)	N25—H25B	0.8600
Se9—C9	2.06 (4)	N25—C5	1.42 (3)
C6—N16	1.30 (3)	N17—H17A	0.8600
C6—N26	1.29 (3)	N17—H17B	0.8600
C2—N21	1.25 (5)	N17—C7	1.23 (4)
C2—N22	1.44 (6)	N18—H18A	0.8600
C9—N19	1.11 (4)	N18—H18B	0.8600
C9—N29	1.13 (4)	N18—C8	1.44 (5)
C3—N23	1.35 (4)	N23—H23A	0.8600
C3—N13	1.34 (4)	N23—H23B	0.8600
C1—N11	1.38 (3)	N14—H14A	0.8600
C1—N12	1.24 (3)	N14—H14B	0.8600
N16—H16A	0.8600	N14—C4	1.33 (5)
N16—H16B	0.8600	N24—H24A	0.8600
N21—H21A	0.8600	N24—H24B	0.8600
N21—H21B	0.8600	N24—C4	1.33 (5)
N19—H19A	0.8600	N27—H27A	0.8600
N19—H19B	0.8600	N27—H27B	0.8600
N29—H29A	0.8600	N27—C7	1.34 (4)
N29—H29B	0.8600	N13—H13A	0.8600
N22—H22A	0.8600	N13—H13B	0.8600
N22—H22B	0.8600	C5—N15	1.28 (3)
N26—H26A	0.8600	N15—H15A	0.8600
N26—H26B	0.8600	N15—H15B	0.8600
N11—H11A	0.8600
N16—C6—Se6	120.7 (19)	C8—N28—H28B	120.0
N26—C6—Se6	117.4 (19)	H25A—N25—H25B	120.0
N26—C6—N16	122 (2)	C5—N25—H25A	120.0
N21—C2—Se2	127 (4)	C5—N25—H25B	120.0
N21—C2—N22	119 (4)	H17A—N17—H17B	120.0
N22—C2—Se2	114 (4)	C7—N17—H17A	120.0
N19—C9—Se9	114 (3)	C7—N17—H17B	120.0
N19—C9—N29	132 (4)	H18A—N18—H18B	120.0
N29—C9—Se9	112 (3)	C8—N18—H18A	120.0
N23—C3—Se3	124 (2)	C8—N18—H18B	120.0
N13—C3—Se3	122 (2)	C3—N23—H23A	120.0
N13—C3—N23	114 (3)	C3—N23—H23B	120.0
N11—C1—Se1	116.1 (19)	H23A—N23—H23B	120.0
N12—C1—Se1	125 (2)	H14A—N14—H14B	120.0
N12—C1—N11	118 (2)	C4—N14—H14A	120.0
C6—N16—H16A	120.0	C4—N14—H14B	120.0
C6—N16—H16B	120.0	H24A—N24—H24B	120.0
H16A—N16—H16B	120.0	C4—N24—H24A	120.0
C2—N21—H21A	120.0	C4—N24—H24B	120.0
C2—N21—H21B	120.0	H27A—N27—H27B	120.0
H21A—N21—H21B	120.0	C7—N27—H27A	120.0
C9—N19—H19A	120.0	C7—N27—H27B	120.0
C9—N19—H19B	120.0	C3—N13—H13A	120.0
H19A—N19—H19B	120.0	C3—N13—H13B	120.0
C9—N29—H29A	120.0	H13A—N13—H13B	120.0
C9—N29—H29B	120.0	N17—C7—Se7	122 (3)
H29A—N29—H29B	120.0	N17—C7—N27	118 (3)
C2—N22—H22A	120.0	N27—C7—Se7	120 (3)
C2—N22—H22B	120.0	N25—C5—Se5	119.0 (17)
H22A—N22—H22B	120.0	N15—C5—Se5	124.5 (18)
C6—N26—H26A	120.0	N15—C5—N25	115 (2)
C6—N26—H26B	120.0	N28—C8—Se8	128 (3)
H26A—N26—H26B	120.0	N28—C8—N18	111 (3)
C1—N11—H11A	120.0	N18—C8—Se8	121 (3)
C1—N11—H11B	120.0	N14—C4—Se4	119 (4)
H11A—N11—H11B	120.0	N14—C4—N24	128 (5)
C1—N12—H12A	120.0	N24—C4—Se4	113 (3)
C1—N12—H12B	120.0	C5—N15—H15A	120.0
H12A—N12—H12B	120.0	C5—N15—H15B	120.0
H28A—N28—H28B	120.0	H15A—N15—H15B	120.0
C8—N28—H28A	120.0

Selenourea (phase_alpha_Selenourea_333K)

Crystal data

CH4N2Se	Dx = 2.086 Mg m^−3
Mr = 123.02	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P31	Cell parameters from 3264 reflections
a = 15.3150 (6) Å	θ = 4.1–25.9°
c = 13.0481 (5) Å	µ = 9.36 mm^−1
V = 2650.4 (2) Å^3	T = 333 K
Z = 27	Plate, orange
F(000) = 1566	0.25 × 0.10 × 0.05 mm

Data collection

Xcalibur, Eos diffractometer	8258 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	5566 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 16.1544 pixels mm^-1	θmax = 29.0°, θmin = 3.1°
ω scans	h = −20→20
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −19→19
Tmin = 0.338, Tmax = 0.626	l = −17→17
28577 measured reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0127P)^2 + 41.939P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.078	(Δ/σ)max < 0.001
wR(F^2) = 0.149	Δρmax = 0.56 e Å^−3
S = 1.06	Δρmin = −1.90 e Å^−3
8258 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
326 parameters	Extinction coefficient: 0.00065 (5)
80 restraints	Absolute structure: Refined as a perfect inversion twin.
Primary atom site location: dual	Absolute structure parameter: 0.5
Hydrogen site location: inferred from neighbouring sites

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component perfect inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	0.30573 (18)	0.35167 (17)	0.09650 (16)	0.0385 (5)
Se2	0.39302 (19)	0.36063 (19)	0.75571 (17)	0.0406 (6)
Se3	0.30470 (18)	0.27103 (17)	0.42838 (18)	0.0385 (5)
Se4	0.6316 (2)	0.6084 (2)	0.70808 (16)	0.0464 (7)
Se5	0.72130 (18)	0.69301 (19)	0.04964 (19)	0.0428 (6)
Se6	0.63446 (18)	0.7016 (2)	0.38266 (16)	0.0384 (5)
Se7	0.73160 (19)	0.3737 (2)	0.46959 (18)	0.0544 (8)
Se8	0.29941 (19)	0.70144 (18)	0.6668 (2)	0.0476 (7)
Se9	1.06956 (19)	1.0320 (2)	0.4659 (2)	0.0556 (7)
C6	0.7429 (15)	0.6773 (18)	0.3881 (16)	0.044 (5)
C2	0.261 (3)	0.322 (3)	0.761 (3)	0.083 (9)
C9	0.927 (2)	0.9885 (19)	0.4623 (18)	0.055 (6)
C3	0.4113 (17)	0.4023 (16)	0.4178 (16)	0.045 (5)
C1	0.3820 (16)	0.2900 (17)	0.0935 (14)	0.037 (5)
N16	0.7999 (13)	0.6908 (15)	0.3090 (13)	0.052 (5)
H16A	0.852286	0.684285	0.315072	0.062*
H16B	0.785333	0.706357	0.250653	0.062*
N21	0.2063 (19)	0.3071 (19)	0.8399 (18)	0.083 (7)
H21A	0.141715	0.276139	0.834338	0.100*
H21B	0.234068	0.327628	0.898997	0.100*
N19	0.8871 (18)	0.996 (2)	0.5379 (18)	0.096 (10)
H19A	0.827506	0.988607	0.534297	0.116*
H19B	0.917934	1.009791	0.595843	0.116*
N29	0.8860 (18)	0.9697 (19)	0.3793 (18)	0.081 (7)
H29A	0.826410	0.961538	0.373444	0.097*
H29B	0.916416	0.964468	0.326291	0.097*
N22	0.205 (2)	0.285 (2)	0.669 (2)	0.118 (10)
H22A	0.140102	0.254398	0.669789	0.142*
H22B	0.236019	0.291898	0.611687	0.142*
N26	0.7650 (16)	0.6538 (16)	0.4769 (15)	0.061 (5)
H26A	0.817287	0.647169	0.483053	0.074*
H26B	0.727171	0.644829	0.529177	0.074*
N11	0.4337 (13)	0.2924 (14)	0.0084 (12)	0.044 (4)
H11A	0.468927	0.262939	0.008151	0.053*
H11B	0.431287	0.323533	−0.045515	0.053*
N12	0.3899 (17)	0.2410 (18)	0.1719 (13)	0.072 (7)
H12A	0.426282	0.212877	0.167291	0.087*
H12B	0.358644	0.236891	0.228099	0.087*
N28	0.3925 (17)	0.6042 (16)	0.7555 (16)	0.064 (6)
H28A	0.437576	0.586355	0.754531	0.077*
H28B	0.360153	0.599005	0.811141	0.077*
N25	0.5293 (13)	0.6226 (16)	0.1302 (14)	0.060 (6)
H25A	0.464702	0.594576	0.127904	0.072*
H25B	0.561037	0.650980	0.185785	0.072*
N17	0.5441 (15)	0.2473 (15)	0.3887 (16)	0.063 (6)
H17A	0.479392	0.210994	0.388822	0.076*
H17B	0.577173	0.255131	0.332945	0.076*
N18	0.4294 (18)	0.645 (2)	0.5855 (18)	0.084 (7)
H18A	0.473496	0.626038	0.589351	0.100*
H18B	0.420172	0.667490	0.528501	0.100*
N23	0.4715 (16)	0.4480 (17)	0.4970 (16)	0.076 (7)
H23A	0.519757	0.509314	0.491416	0.091*
H23B	0.462261	0.416218	0.553964	0.091*
N14	0.678 (3)	0.799 (3)	0.643 (3)	0.132 (12)
H14A	0.701950	0.862955	0.644921	0.158*
H14B	0.643331	0.764969	0.590292	0.158*
N24	0.741 (2)	0.793 (2)	0.801 (2)	0.105 (9)
H24A	0.768474	0.857147	0.809610	0.126*
H24B	0.747103	0.756382	0.846782	0.126*
N27	0.543 (2)	0.279 (2)	0.557 (2)	0.099 (9)
H27A	0.478242	0.243070	0.557968	0.119*
H27B	0.575529	0.308126	0.611652	0.119*
N13	0.4291 (19)	0.4550 (19)	0.3320 (18)	0.089 (7)
H13A	0.478057	0.516186	0.329269	0.107*
H13B	0.391615	0.427916	0.279109	0.107*
C7	0.5913 (18)	0.2899 (16)	0.4718 (18)	0.054 (6)
C5	0.5831 (13)	0.6220 (15)	0.0431 (14)	0.031 (4)
C8	0.373 (2)	0.640 (3)	0.6716 (18)	0.076 (9)
C4	0.692 (2)	0.753 (2)	0.7186 (16)	0.070 (9)
N15	0.5301 (14)	0.5779 (17)	−0.0372 (15)	0.072 (7)
H15A	0.465558	0.551003	−0.035413	0.086*
H15B	0.559247	0.575341	−0.092556	0.086*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0423 (14)	0.0377 (12)	0.0381 (11)	0.0220 (11)	−0.0040 (9)	0.0019 (10)
Se2	0.0352 (13)	0.0437 (13)	0.0440 (13)	0.0205 (11)	−0.0030 (10)	−0.0015 (10)
Se3	0.0407 (13)	0.0316 (11)	0.0378 (10)	0.0141 (11)	0.0026 (10)	−0.0002 (10)
Se4	0.0486 (14)	0.0405 (14)	0.0457 (15)	0.0190 (12)	−0.0057 (11)	−0.0030 (10)
Se5	0.0371 (13)	0.0471 (14)	0.0451 (13)	0.0217 (11)	0.0029 (10)	0.0057 (10)
Se6	0.0412 (13)	0.0439 (13)	0.0390 (12)	0.0280 (11)	−0.0012 (10)	−0.0026 (9)
Se7	0.0375 (14)	0.0496 (15)	0.0528 (16)	0.0042 (11)	0.0009 (11)	0.0084 (11)
Se8	0.0585 (16)	0.0488 (14)	0.0483 (14)	0.0364 (13)	−0.0077 (11)	−0.0053 (11)
Se9	0.0408 (14)	0.0602 (17)	0.0590 (16)	0.0202 (13)	−0.0002 (12)	0.0064 (12)
C6	0.032 (11)	0.069 (16)	0.045 (12)	0.037 (12)	0.003 (9)	0.003 (11)
C2	0.085 (10)	0.085 (10)	0.081 (10)	0.043 (6)	0.001 (5)	−0.004 (5)
C9	0.081 (18)	0.052 (14)	0.048 (14)	0.046 (14)	−0.007 (13)	0.011 (11)
C3	0.055 (14)	0.034 (11)	0.033 (10)	0.012 (10)	0.003 (10)	0.007 (9)
C1	0.033 (11)	0.054 (13)	0.026 (10)	0.023 (10)	0.011 (8)	0.000 (9)
N16	0.041 (10)	0.097 (16)	0.041 (10)	0.052 (11)	−0.007 (8)	−0.012 (10)
N21	0.069 (10)	0.104 (12)	0.069 (10)	0.038 (8)	0.002 (8)	0.003 (9)
N19	0.071 (16)	0.17 (3)	0.069 (16)	0.072 (18)	−0.023 (13)	−0.053 (17)
N29	0.066 (10)	0.097 (11)	0.070 (11)	0.033 (8)	−0.017 (8)	−0.001 (8)
N22	0.107 (13)	0.141 (14)	0.112 (14)	0.065 (10)	0.002 (10)	−0.006 (10)
N26	0.063 (9)	0.086 (10)	0.058 (9)	0.054 (8)	−0.002 (7)	0.005 (8)
N11	0.054 (11)	0.063 (12)	0.027 (8)	0.038 (10)	0.003 (8)	0.008 (8)
N12	0.107 (18)	0.14 (2)	0.021 (9)	0.103 (18)	0.014 (10)	0.016 (11)
N28	0.076 (10)	0.081 (10)	0.052 (9)	0.051 (8)	0.008 (8)	0.008 (8)
N25	0.026 (9)	0.098 (16)	0.046 (11)	0.023 (10)	0.016 (8)	−0.010 (11)
N17	0.048 (9)	0.063 (10)	0.055 (9)	0.010 (7)	0.000 (7)	−0.013 (8)
N18	0.085 (11)	0.112 (12)	0.076 (11)	0.066 (9)	0.005 (8)	0.010 (9)
N23	0.069 (15)	0.061 (14)	0.051 (12)	−0.001 (11)	0.008 (11)	−0.019 (10)
N14	0.133 (12)	0.131 (12)	0.131 (12)	0.065 (6)	−0.001 (3)	0.000 (3)
N24	0.114 (13)	0.100 (13)	0.097 (13)	0.051 (9)	−0.004 (9)	0.008 (9)
N27	0.083 (12)	0.116 (13)	0.086 (12)	0.040 (9)	−0.004 (9)	0.005 (9)
N13	0.098 (12)	0.069 (10)	0.067 (10)	0.016 (8)	−0.001 (9)	−0.002 (8)
C7	0.051 (7)	0.061 (8)	0.055 (8)	0.033 (5)	0.000 (5)	−0.001 (5)
C5	0.023 (9)	0.047 (12)	0.026 (9)	0.020 (9)	0.011 (7)	0.001 (8)
C8	0.09 (2)	0.16 (3)	0.034 (12)	0.10 (2)	0.012 (12)	0.029 (15)
C4	0.10 (2)	0.12 (2)	0.029 (12)	0.09 (2)	−0.029 (13)	−0.023 (14)
N15	0.040 (11)	0.090 (16)	0.056 (12)	0.010 (11)	−0.014 (9)	−0.045 (12)

Geometric parameters (Å, º)

Se1—C1	1.83 (2)	N11—H11B	0.8600
Se2—C2	1.81 (3)	N12—H12A	0.8600
Se3—C3	1.86 (2)	N12—H12B	0.8600
Se4—C4	1.93 (3)	N28—H28A	0.8600
Se5—C5	1.835 (18)	N28—H28B	0.8600
Se6—C6	1.876 (19)	N28—C8	1.32 (3)
Se7—C7	1.87 (2)	N25—H25A	0.8600
Se8—C8	1.80 (2)	N25—H25B	0.8600
Se9—C9	1.94 (3)	N25—C5	1.41 (2)
C6—N16	1.30 (3)	N17—H17A	0.8600
C6—N26	1.31 (3)	N17—H17B	0.8600
C2—N21	1.27 (4)	N17—C7	1.29 (3)
C2—N22	1.42 (4)	N18—H18A	0.8600
C9—N19	1.20 (3)	N18—H18B	0.8600
C9—N29	1.21 (3)	N18—C8	1.39 (3)
C3—N23	1.33 (3)	N23—H23A	0.8600
C3—N13	1.33 (3)	N23—H23B	0.8600
C1—N11	1.35 (2)	N14—H14A	0.8600
C1—N12	1.31 (3)	N14—H14B	0.8600
N16—H16A	0.8600	N14—C4	1.30 (4)
N16—H16B	0.8600	N24—H24A	0.8600
N21—H21A	0.8600	N24—H24B	0.8600
N21—H21B	0.8600	N24—C4	1.27 (3)
N19—H19A	0.8600	N27—H27A	0.8600
N19—H19B	0.8600	N27—H27B	0.8600
N29—H29A	0.8600	N27—C7	1.30 (3)
N29—H29B	0.8600	N13—H13A	0.8600
N22—H22A	0.8600	N13—H13B	0.8600
N22—H22B	0.8600	C5—N15	1.29 (2)
N26—H26A	0.8600	N15—H15A	0.8600
N26—H26B	0.8600	N15—H15B	0.8600
N11—H11A	0.8600
N16—C6—Se6	122.0 (15)	C8—N28—H28B	120.0
N16—C6—N26	120.1 (19)	H25A—N25—H25B	120.0
N26—C6—Se6	117.8 (15)	C5—N25—H25A	120.0
N21—C2—Se2	128 (3)	C5—N25—H25B	120.0
N21—C2—N22	114 (3)	H17A—N17—H17B	120.0
N22—C2—Se2	116 (2)	C7—N17—H17A	120.0
N19—C9—Se9	119 (2)	C7—N17—H17B	120.0
N19—C9—N29	122 (3)	H18A—N18—H18B	120.0
N29—C9—Se9	118 (2)	C8—N18—H18A	120.0
N23—C3—Se3	121.0 (16)	C8—N18—H18B	120.0
N13—C3—Se3	121.6 (18)	C3—N23—H23A	120.0
N13—C3—N23	117 (2)	C3—N23—H23B	120.0
N11—C1—Se1	121.2 (15)	H23A—N23—H23B	120.0
N12—C1—Se1	122.9 (14)	H14A—N14—H14B	120.0
N12—C1—N11	115.9 (18)	C4—N14—H14A	120.0
C6—N16—H16A	120.0	C4—N14—H14B	120.0
C6—N16—H16B	120.0	H24A—N24—H24B	120.0
H16A—N16—H16B	120.0	C4—N24—H24A	120.0
C2—N21—H21A	120.0	C4—N24—H24B	120.0
C2—N21—H21B	120.0	H27A—N27—H27B	120.0
H21A—N21—H21B	120.0	C7—N27—H27A	120.0
C9—N19—H19A	120.0	C7—N27—H27B	120.0
C9—N19—H19B	120.0	C3—N13—H13A	120.0
H19A—N19—H19B	120.0	C3—N13—H13B	120.0
C9—N29—H29A	120.0	H13A—N13—H13B	120.0
C9—N29—H29B	120.0	N17—C7—Se7	119.7 (19)
H29A—N29—H29B	120.0	N17—C7—N27	121 (3)
C2—N22—H22A	120.0	N27—C7—Se7	119 (2)
C2—N22—H22B	120.0	N25—C5—Se5	117.6 (14)
H22A—N22—H22B	120.0	N15—C5—Se5	125.8 (14)
C6—N26—H26A	120.0	N15—C5—N25	116.2 (17)
C6—N26—H26B	120.0	N28—C8—Se8	125.0 (19)
H26A—N26—H26B	120.0	N28—C8—N18	116 (2)
C1—N11—H11A	120.0	N18—C8—Se8	118.2 (18)
C1—N11—H11B	120.0	N14—C4—Se4	117 (2)
H11A—N11—H11B	120.0	N24—C4—Se4	116 (2)
C1—N12—H12A	120.0	N24—C4—N14	127 (3)
C1—N12—H12B	120.0	C5—N15—H15A	120.0
H12A—N12—H12B	120.0	C5—N15—H15B	120.0
H28A—N28—H28B	120.0	H15A—N15—H15B	120.0
C8—N28—H28A	120.0

Selenourea (phase_alpha_Selenourea_343K)

Crystal data

CH4N2Se	Dx = 2.082 Mg m^−3
Mr = 123.02	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P31	Cell parameters from 3181 reflections
a = 15.3269 (7) Å	θ = 4.1–25.9°
c = 13.0553 (5) Å	µ = 9.34 mm^−1
V = 2655.99 (3) Å^3	T = 343 K
Z = 27	Plate, orange
F(000) = 1566	0.25 × 0.10 × 0.05 mm

Data collection

Xcalibur, Eos diffractometer	8276 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	5485 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 16.1544 pixels mm^-1	θmax = 29.0°, θmin = 3.1°
ω scans	h = −20→20
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −19→19
Tmin = 0.597, Tmax = 1.000	l = −17→17
28565 measured reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0071P)^2 + 37.1154P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.078	(Δ/σ)max < 0.001
wR(F^2) = 0.139	Δρmax = 1.37 e Å^−3
S = 1.06	Δρmin = −1.65 e Å^−3
8276 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
326 parameters	Extinction coefficient: 0.00064 (4)
75 restraints	Absolute structure: Refined as a perfect inversion twin.
Primary atom site location: dual	Absolute structure parameter: 0.5
Hydrogen site location: inferred from neighbouring sites

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component perfect inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	0.30538 (18)	0.35148 (17)	0.09639 (16)	0.0409 (5)
Se2	0.39240 (19)	0.36049 (19)	0.75586 (17)	0.0425 (6)
Se3	0.30475 (18)	0.27110 (17)	0.42829 (18)	0.0403 (5)
Se4	0.6315 (2)	0.6082 (2)	0.70829 (16)	0.0485 (7)
Se5	0.72138 (18)	0.69267 (19)	0.04962 (19)	0.0442 (6)
Se6	0.63445 (18)	0.7013 (2)	0.38280 (16)	0.0407 (5)
Se7	0.73181 (18)	0.3736 (2)	0.46903 (18)	0.0566 (8)
Se8	0.29944 (19)	0.70143 (18)	0.6671 (2)	0.0490 (7)
Se9	1.06962 (19)	1.0322 (2)	0.46571 (19)	0.0578 (7)
C6	0.7431 (16)	0.6772 (17)	0.3872 (16)	0.046 (5)
C2	0.258 (2)	0.3173 (17)	0.761 (2)	0.076 (8)
C9	0.927 (2)	0.9877 (18)	0.4618 (18)	0.060 (7)
C3	0.4095 (17)	0.4019 (16)	0.4191 (16)	0.048 (5)
C1	0.3828 (16)	0.2889 (18)	0.0943 (14)	0.041 (5)
N16	0.8000 (13)	0.6904 (15)	0.3092 (13)	0.058 (5)
H16A	0.851983	0.683359	0.315531	0.069*
H16B	0.785937	0.706258	0.250734	0.069*
N21	0.2061 (19)	0.3101 (18)	0.8387 (18)	0.089 (7)
H21A	0.142050	0.284592	0.832889	0.107*
H21B	0.234589	0.330706	0.897432	0.107*
N19	0.8875 (17)	0.998 (2)	0.5369 (18)	0.097 (9)
H19A	0.828467	0.991089	0.532799	0.116*
H19B	0.918276	1.011428	0.594839	0.116*
N29	0.8866 (17)	0.9684 (18)	0.3788 (17)	0.082 (7)
H29A	0.827563	0.961278	0.372015	0.098*
H29B	0.916937	0.961711	0.326606	0.098*
N22	0.203 (2)	0.281 (2)	0.668 (2)	0.122 (10)
H22A	0.139209	0.256265	0.667694	0.147*
H22B	0.234590	0.283722	0.612472	0.147*
N26	0.7640 (15)	0.6531 (16)	0.4761 (15)	0.065 (5)
H26A	0.815924	0.646023	0.482745	0.078*
H26B	0.725877	0.644400	0.527913	0.078*
N11	0.4334 (13)	0.2924 (13)	0.0089 (12)	0.046 (4)
H11A	0.468500	0.262821	0.007329	0.055*
H11B	0.430574	0.324138	−0.044132	0.055*
N12	0.3888 (17)	0.2406 (18)	0.1723 (12)	0.076 (7)
H12A	0.424386	0.211657	0.168892	0.091*
H12B	0.357064	0.237344	0.227870	0.091*
N28	0.3913 (17)	0.6025 (16)	0.7555 (17)	0.073 (6)
H28A	0.431629	0.578881	0.751968	0.087*
H28B	0.361424	0.599565	0.812249	0.087*
N25	0.5306 (12)	0.6224 (15)	0.1301 (13)	0.060 (6)
H25A	0.466040	0.594962	0.128044	0.071*
H25B	0.562520	0.650301	0.185720	0.071*
N17	0.5432 (16)	0.2471 (16)	0.3893 (17)	0.070 (6)
H17A	0.478381	0.214327	0.387693	0.084*
H17B	0.576924	0.252440	0.334700	0.084*
N18	0.4286 (17)	0.6435 (19)	0.5858 (18)	0.085 (7)
H18A	0.467463	0.618111	0.589365	0.102*
H18B	0.422755	0.668575	0.529004	0.102*
N23	0.4708 (16)	0.4478 (16)	0.4974 (15)	0.080 (7)
H23A	0.519698	0.508621	0.490866	0.096*
H23B	0.461676	0.416646	0.554693	0.096*
N14	0.682 (2)	0.799 (2)	0.643 (2)	0.127 (11)
H14A	0.709755	0.863358	0.644794	0.152*
H14B	0.648773	0.766380	0.589286	0.152*
N24	0.741 (2)	0.794 (2)	0.802 (2)	0.111 (9)
H24A	0.769684	0.858017	0.808470	0.133*
H24B	0.744230	0.757597	0.850296	0.133*
N27	0.543 (2)	0.282 (2)	0.556 (2)	0.107 (9)
H27A	0.477926	0.250303	0.557960	0.129*
H27B	0.576938	0.310993	0.610034	0.129*
N13	0.4288 (19)	0.4556 (18)	0.3322 (17)	0.089 (7)
H13A	0.478685	0.516241	0.329516	0.107*
H13B	0.391269	0.429195	0.279215	0.107*
C7	0.588 (2)	0.287 (3)	0.4712 (18)	0.078 (10)
C5	0.5831 (14)	0.6217 (15)	0.0438 (14)	0.037 (4)
C8	0.3749 (16)	0.6440 (17)	0.6724 (18)	0.083 (10)
C4	0.692 (2)	0.751 (2)	0.7186 (16)	0.070 (9)
N15	0.5305 (15)	0.5786 (17)	−0.0368 (15)	0.077 (7)
H15A	0.466088	0.552165	−0.035365	0.092*
H15B	0.559857	0.576390	−0.092122	0.092*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0455 (14)	0.0395 (12)	0.0402 (11)	0.0230 (11)	−0.0044 (10)	0.0028 (10)
Se2	0.0363 (13)	0.0463 (13)	0.0453 (13)	0.0211 (11)	−0.0038 (10)	−0.0014 (10)
Se3	0.0422 (13)	0.0325 (11)	0.0405 (10)	0.0142 (11)	0.0037 (10)	0.0007 (10)
Se4	0.0497 (14)	0.0428 (14)	0.0488 (15)	0.0200 (12)	−0.0048 (11)	−0.0037 (10)
Se5	0.0389 (13)	0.0474 (13)	0.0477 (13)	0.0226 (11)	0.0031 (10)	0.0058 (10)
Se6	0.0438 (13)	0.0464 (13)	0.0409 (12)	0.0293 (11)	−0.0009 (10)	−0.0019 (9)
Se7	0.0396 (14)	0.0516 (15)	0.0557 (16)	0.0054 (11)	0.0010 (11)	0.0084 (11)
Se8	0.0607 (16)	0.0494 (14)	0.0494 (14)	0.0368 (13)	−0.0066 (11)	−0.0046 (11)
Se9	0.0435 (14)	0.0611 (17)	0.0623 (16)	0.0213 (13)	−0.0007 (12)	0.0060 (12)
C6	0.039 (11)	0.065 (15)	0.052 (13)	0.039 (12)	0.004 (9)	0.008 (11)
C2	0.078 (9)	0.078 (9)	0.074 (9)	0.040 (6)	0.000 (5)	−0.004 (5)
C9	0.09 (2)	0.049 (14)	0.048 (14)	0.039 (15)	−0.007 (13)	0.013 (11)
C3	0.058 (14)	0.039 (12)	0.035 (10)	0.015 (10)	0.002 (10)	0.004 (9)
C1	0.035 (11)	0.065 (15)	0.029 (10)	0.029 (11)	0.016 (8)	0.000 (9)
N16	0.048 (11)	0.104 (16)	0.048 (11)	0.058 (12)	−0.006 (9)	−0.013 (10)
N21	0.074 (10)	0.112 (12)	0.074 (10)	0.041 (9)	0.007 (8)	0.001 (9)
N19	0.073 (16)	0.17 (3)	0.072 (16)	0.077 (18)	−0.023 (13)	−0.046 (17)
N29	0.067 (10)	0.097 (11)	0.068 (10)	0.031 (8)	−0.016 (8)	0.000 (8)
N22	0.110 (13)	0.147 (14)	0.115 (14)	0.068 (10)	0.003 (10)	−0.006 (10)
N26	0.063 (9)	0.092 (10)	0.068 (10)	0.058 (8)	0.000 (7)	0.006 (8)
N11	0.057 (11)	0.062 (12)	0.031 (9)	0.039 (10)	0.001 (8)	0.006 (8)
N12	0.111 (18)	0.15 (2)	0.019 (8)	0.108 (18)	0.011 (10)	0.018 (11)
N28	0.085 (10)	0.086 (10)	0.062 (9)	0.054 (8)	0.008 (8)	0.010 (8)
N25	0.020 (8)	0.100 (16)	0.045 (10)	0.020 (9)	0.010 (7)	−0.015 (10)
N17	0.053 (9)	0.073 (10)	0.061 (9)	0.016 (7)	0.000 (8)	−0.013 (8)
N18	0.088 (11)	0.114 (11)	0.078 (11)	0.069 (9)	0.006 (8)	0.009 (8)
N23	0.073 (15)	0.059 (13)	0.055 (12)	−0.005 (11)	0.007 (11)	−0.022 (10)
N14	0.141 (14)	0.111 (14)	0.115 (14)	0.052 (10)	−0.011 (10)	0.004 (10)
N24	0.122 (13)	0.103 (13)	0.103 (13)	0.053 (10)	−0.005 (9)	0.008 (9)
N27	0.094 (12)	0.123 (13)	0.093 (12)	0.045 (9)	−0.006 (9)	0.002 (9)
N13	0.097 (11)	0.071 (10)	0.066 (10)	0.016 (8)	−0.003 (9)	0.000 (8)
C7	0.10 (2)	0.17 (3)	0.039 (13)	0.12 (2)	0.005 (13)	0.000 (16)
C5	0.031 (10)	0.048 (12)	0.030 (9)	0.018 (9)	0.012 (8)	0.001 (9)
C8	0.11 (2)	0.17 (3)	0.043 (13)	0.12 (2)	0.015 (13)	0.028 (16)
C4	0.10 (2)	0.12 (2)	0.030 (12)	0.08 (2)	−0.027 (13)	−0.016 (13)
N15	0.048 (12)	0.094 (17)	0.054 (12)	0.010 (12)	−0.014 (10)	−0.042 (12)

Geometric parameters (Å, º)

Se1—C1	1.86 (2)	N11—H11B	0.8600
Se2—C2	1.82 (3)	N12—H12A	0.8600
Se3—C3	1.84 (2)	N12—H12B	0.8600
Se4—C4	1.91 (3)	N28—H28A	0.8600
Se5—C5	1.837 (19)	N28—H28B	0.8600
Se6—C6	1.878 (19)	N28—C8	1.34 (3)
Se7—C7	1.92 (3)	N25—H25A	0.8600
Se8—C8	1.77 (2)	N25—H25B	0.8600
Se9—C9	1.94 (3)	N25—C5	1.39 (2)
C6—N16	1.29 (3)	N17—H17A	0.8600
C6—N26	1.30 (3)	N17—H17B	0.8600
C2—N21	1.26 (3)	N17—C7	1.26 (3)
C2—N22	1.42 (4)	N18—H18A	0.8600
C9—N19	1.20 (3)	N18—H18B	0.8600
C9—N29	1.21 (3)	N18—C8	1.40 (3)
C3—N23	1.33 (3)	N23—H23A	0.8600
C3—N13	1.34 (3)	N23—H23B	0.8600
C1—N11	1.34 (2)	N14—H14A	0.8600
C1—N12	1.29 (3)	N14—H14B	0.8600
N16—H16A	0.8600	N14—C4	1.28 (3)
N16—H16B	0.8600	N24—H24A	0.8600
N21—H21A	0.8600	N24—H24B	0.8600
N21—H21B	0.8600	N24—C4	1.30 (3)
N19—H19A	0.8600	N27—H27A	0.8600
N19—H19B	0.8600	N27—H27B	0.8600
N29—H29A	0.8600	N27—C7	1.29 (3)
N29—H29B	0.8600	N13—H13A	0.8600
N22—H22A	0.8600	N13—H13B	0.8600
N22—H22B	0.8600	C5—N15	1.29 (3)
N26—H26A	0.8600	N15—H15A	0.8600
N26—H26B	0.8600	N15—H15B	0.8600
N11—H11A	0.8600
N16—C6—Se6	122.8 (15)	C8—N28—H28B	120.0
N16—C6—N26	120.3 (19)	H25A—N25—H25B	120.0
N26—C6—Se6	116.8 (16)	C5—N25—H25A	120.0
N21—C2—Se2	128 (2)	C5—N25—H25B	120.0
N21—C2—N22	115 (3)	H17A—N17—H17B	120.0
N22—C2—Se2	116 (2)	C7—N17—H17A	120.0
N19—C9—Se9	119 (2)	C7—N17—H17B	120.0
N19—C9—N29	122 (3)	H18A—N18—H18B	120.0
N29—C9—Se9	117 (2)	C8—N18—H18A	120.0
N23—C3—Se3	121.8 (17)	C8—N18—H18B	120.0
N23—C3—N13	116 (2)	C3—N23—H23A	120.0
N13—C3—Se3	121.7 (17)	C3—N23—H23B	120.0
N11—C1—Se1	119.7 (15)	H23A—N23—H23B	120.0
N12—C1—Se1	122.0 (14)	H14A—N14—H14B	120.0
N12—C1—N11	118.3 (19)	C4—N14—H14A	120.0
C6—N16—H16A	120.0	C4—N14—H14B	120.0
C6—N16—H16B	120.0	H24A—N24—H24B	120.0
H16A—N16—H16B	120.0	C4—N24—H24A	120.0
C2—N21—H21A	120.0	C4—N24—H24B	120.0
C2—N21—H21B	120.0	H27A—N27—H27B	120.0
H21A—N21—H21B	120.0	C7—N27—H27A	120.0
C9—N19—H19A	120.0	C7—N27—H27B	120.0
C9—N19—H19B	120.0	C3—N13—H13A	120.0
H19A—N19—H19B	120.0	C3—N13—H13B	120.0
C9—N29—H29A	120.0	H13A—N13—H13B	120.0
C9—N29—H29B	120.0	N17—C7—Se7	119.2 (19)
H29A—N29—H29B	120.0	N17—C7—N27	123 (3)
C2—N22—H22A	120.0	N27—C7—Se7	117 (2)
C2—N22—H22B	120.0	N25—C5—Se5	117.6 (14)
H22A—N22—H22B	120.0	N15—C5—Se5	125.3 (15)
C6—N26—H26A	120.0	N15—C5—N25	116.7 (18)
C6—N26—H26B	120.0	N28—C8—Se8	126.2 (19)
H26A—N26—H26B	120.0	N28—C8—N18	114 (2)
C1—N11—H11A	120.0	N18—C8—Se8	120.2 (18)
C1—N11—H11B	120.0	N14—C4—Se4	118 (2)
H11A—N11—H11B	120.0	N14—C4—N24	124 (3)
C1—N12—H12A	120.0	N24—C4—Se4	118 (2)
C1—N12—H12B	120.0	C5—N15—H15A	120.0
H12A—N12—H12B	120.0	C5—N15—H15B	120.0
H28A—N28—H28B	120.0	H15A—N15—H15B	120.0
C8—N28—H28A	120.0

Selenourea (phase_alpha_Selenourea_353K)

Crystal data

CH4N2Se	Dx = 2.077 Mg m^−3
Mr = 123.02	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P31	Cell parameters from 3095 reflections
a = 15.3389 (7) Å	θ = 4.0–25.8°
c = 13.0642 (6) Å	µ = 9.32 mm^−1
V = 2662.0 (3) Å^3	T = 353 K
Z = 27	Plate, orange
F(000) = 1566	0.25 × 0.10 × 0.05 mm

Data collection

Xcalibur, Eos diffractometer	8281 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	5333 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: 16.1544 pixels mm^-1	θmax = 29.0°, θmin = 3.1°
ω scans	h = −20→20
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −19→19
Tmin = 0.340, Tmax = 0.628	l = −17→17
28618 measured reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0138P)^2 + 32.3626P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.076	(Δ/σ)max < 0.001
wR(F^2) = 0.145	Δρmax = 1.27 e Å^−3
S = 1.05	Δρmin = −1.49 e Å^−3
8281 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
326 parameters	Extinction coefficient: 0.00066 (5)
61 restraints	Absolute structure: Refined as a perfect inversion twin.
Primary atom site location: dual	Absolute structure parameter: 0.5
Hydrogen site location: inferred from neighbouring sites

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component perfect inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	0.30519 (18)	0.35152 (17)	0.09625 (16)	0.0424 (5)
Se2	0.39231 (19)	0.36053 (19)	0.75577 (17)	0.0450 (6)
Se3	0.30503 (17)	0.27123 (16)	0.42827 (17)	0.0423 (5)
Se4	0.6315 (2)	0.6084 (2)	0.70836 (16)	0.0500 (7)
Se5	0.72141 (18)	0.69250 (19)	0.04920 (19)	0.0468 (6)
Se6	0.63476 (18)	0.7013 (2)	0.38302 (15)	0.0425 (5)
Se7	0.73220 (18)	0.37340 (19)	0.46866 (18)	0.0593 (8)
Se8	0.29918 (18)	0.70140 (17)	0.6675 (2)	0.0512 (7)
Se9	1.06954 (18)	1.0325 (2)	0.46576 (19)	0.0598 (7)
C6	0.7430 (16)	0.6762 (17)	0.3871 (16)	0.048 (5)
C2	0.258 (3)	0.319 (3)	0.7625 (19)	0.095 (11)
C9	0.927 (2)	0.9883 (18)	0.4594 (19)	0.063 (7)
C3	0.4080 (16)	0.4014 (15)	0.4191 (15)	0.048 (5)
C1	0.3817 (16)	0.2868 (18)	0.0954 (14)	0.045 (5)
N16	0.7993 (13)	0.6898 (15)	0.3100 (13)	0.059 (5)
H16A	0.851407	0.683040	0.316248	0.071*
H16B	0.785137	0.705718	0.251709	0.071*
N21	0.2050 (18)	0.3091 (18)	0.8400 (17)	0.090 (7)
H21A	0.140518	0.279066	0.834732	0.108*
H21B	0.233292	0.332311	0.898265	0.108*
N19	0.8880 (16)	0.997 (2)	0.5372 (18)	0.095 (8)
H19A	0.828445	0.988569	0.535023	0.115*
H19B	0.920101	1.010274	0.594289	0.115*
N29	0.8863 (18)	0.9695 (19)	0.3793 (19)	0.093 (8)
H29A	0.826623	0.961034	0.374061	0.111*
H29B	0.916238	0.964266	0.325955	0.111*
N22	0.201 (2)	0.277 (2)	0.669 (2)	0.133 (11)
H22A	0.136829	0.247927	0.670251	0.160*
H22B	0.232448	0.280867	0.613309	0.160*
N26	0.7630 (16)	0.6522 (19)	0.4758 (14)	0.073 (6)
H26A	0.814870	0.645184	0.483101	0.087*
H26B	0.724362	0.643268	0.527163	0.087*
N11	0.4327 (13)	0.2927 (13)	0.0082 (11)	0.048 (4)
H11A	0.469234	0.264794	0.005273	0.058*
H11B	0.428350	0.324402	−0.044105	0.058*
N12	0.3883 (17)	0.2405 (18)	0.1713 (13)	0.085 (8)
H12A	0.424958	0.212707	0.168030	0.102*
H12B	0.356183	0.236578	0.226604	0.102*
N28	0.3943 (17)	0.6057 (16)	0.7574 (17)	0.075 (6)
H28A	0.441634	0.591130	0.755654	0.090*
H28B	0.361682	0.598369	0.813256	0.090*
N25	0.5304 (12)	0.6229 (15)	0.1302 (13)	0.066 (6)
H25A	0.465980	0.596116	0.129167	0.079*
H25B	0.563450	0.651546	0.184986	0.079*
N17	0.5442 (15)	0.2486 (16)	0.3873 (16)	0.075 (6)
H17A	0.479475	0.217394	0.385061	0.089*
H17B	0.578112	0.253170	0.333213	0.089*
N18	0.4314 (17)	0.6472 (18)	0.5886 (17)	0.087 (7)
H18A	0.477060	0.630642	0.595066	0.104*
H18B	0.422767	0.668326	0.530579	0.104*
N23	0.4703 (16)	0.4485 (16)	0.4975 (15)	0.084 (7)
H23A	0.518790	0.509383	0.490425	0.101*
H23B	0.461728	0.417876	0.554973	0.101*
N14	0.685 (2)	0.801 (2)	0.641 (2)	0.135 (11)
H14A	0.714419	0.865152	0.643817	0.161*
H14B	0.650809	0.769533	0.587221	0.161*
N24	0.741 (2)	0.793 (2)	0.802 (2)	0.114 (9)
H24A	0.771252	0.857582	0.806433	0.137*
H24B	0.743576	0.757921	0.851760	0.137*
N27	0.542 (2)	0.283 (2)	0.5547 (19)	0.108 (9)
H27A	0.477540	0.252753	0.555601	0.129*
H27B	0.575819	0.310850	0.609485	0.129*
N13	0.4285 (19)	0.4562 (18)	0.3336 (17)	0.097 (8)
H13A	0.478457	0.516858	0.332206	0.117*
H13B	0.391681	0.430896	0.280088	0.117*
C7	0.589 (2)	0.288 (3)	0.4702 (17)	0.077 (9)
C5	0.5812 (13)	0.6200 (15)	0.0431 (15)	0.037 (4)
C8	0.371 (2)	0.640 (2)	0.6726 (17)	0.075 (8)
C4	0.690 (2)	0.748 (2)	0.7195 (18)	0.074 (8)
N15	0.5299 (13)	0.5773 (16)	−0.0357 (14)	0.075 (7)
H15A	0.465517	0.551127	−0.034508	0.090*
H15B	0.559269	0.574399	−0.090584	0.090*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0472 (14)	0.0419 (12)	0.0412 (11)	0.0247 (11)	−0.0035 (9)	0.0026 (10)
Se2	0.0391 (13)	0.0474 (13)	0.0489 (13)	0.0220 (11)	−0.0037 (10)	−0.0008 (10)
Se3	0.0441 (13)	0.0342 (11)	0.0422 (10)	0.0148 (11)	0.0034 (10)	0.0001 (10)
Se4	0.0517 (14)	0.0439 (14)	0.0502 (15)	0.0209 (12)	−0.0052 (11)	−0.0042 (10)
Se5	0.0401 (13)	0.0504 (14)	0.0512 (13)	0.0235 (11)	0.0023 (10)	0.0064 (10)
Se6	0.0451 (13)	0.0488 (13)	0.0423 (12)	0.0301 (11)	0.0004 (10)	−0.0017 (9)
Se7	0.0417 (14)	0.0553 (15)	0.0576 (16)	0.0066 (11)	0.0008 (11)	0.0068 (11)
Se8	0.0616 (16)	0.0508 (14)	0.0531 (14)	0.0372 (12)	−0.0064 (11)	−0.0044 (11)
Se9	0.0441 (14)	0.0631 (17)	0.0651 (16)	0.0215 (13)	−0.0007 (12)	0.0069 (12)
C6	0.041 (11)	0.069 (15)	0.054 (13)	0.042 (12)	0.007 (10)	0.011 (11)
C2	0.13 (3)	0.14 (3)	0.040 (14)	0.09 (2)	−0.027 (16)	−0.043 (17)
C9	0.09 (2)	0.051 (14)	0.055 (15)	0.043 (15)	−0.001 (14)	0.013 (12)
C3	0.049 (13)	0.036 (11)	0.037 (10)	0.005 (10)	0.003 (9)	0.000 (9)
C1	0.040 (12)	0.066 (15)	0.026 (10)	0.024 (11)	0.017 (8)	−0.004 (9)
N16	0.048 (11)	0.104 (16)	0.050 (10)	0.057 (12)	−0.003 (9)	−0.002 (10)
N21	0.077 (10)	0.114 (12)	0.072 (10)	0.042 (8)	0.008 (8)	−0.003 (9)
N19	0.066 (15)	0.15 (3)	0.087 (17)	0.070 (17)	−0.033 (13)	−0.046 (17)
N29	0.076 (11)	0.108 (12)	0.085 (11)	0.039 (9)	−0.017 (9)	0.001 (9)
N22	0.124 (14)	0.153 (15)	0.124 (14)	0.070 (10)	0.002 (10)	−0.006 (10)
N26	0.070 (9)	0.101 (10)	0.076 (10)	0.065 (8)	0.003 (7)	0.007 (8)
N11	0.060 (11)	0.063 (11)	0.035 (9)	0.041 (10)	0.006 (8)	0.011 (8)
N12	0.114 (19)	0.17 (2)	0.026 (9)	0.109 (18)	0.015 (10)	0.028 (12)
N28	0.086 (10)	0.087 (10)	0.062 (9)	0.052 (8)	0.011 (8)	0.011 (8)
N25	0.016 (8)	0.102 (16)	0.057 (11)	0.013 (9)	0.015 (8)	−0.018 (11)
N17	0.057 (9)	0.079 (10)	0.061 (9)	0.013 (7)	−0.004 (8)	−0.016 (8)
N18	0.090 (11)	0.113 (11)	0.077 (10)	0.066 (9)	0.005 (8)	0.013 (8)
N23	0.077 (15)	0.063 (14)	0.062 (13)	−0.002 (12)	0.008 (11)	−0.017 (10)
N14	0.150 (14)	0.117 (14)	0.123 (14)	0.056 (10)	−0.008 (10)	0.005 (10)
N24	0.126 (13)	0.108 (13)	0.103 (13)	0.053 (9)	−0.004 (9)	0.009 (9)
N27	0.092 (12)	0.124 (13)	0.093 (12)	0.043 (9)	−0.002 (9)	0.004 (9)
N13	0.102 (12)	0.080 (11)	0.077 (11)	0.022 (8)	−0.003 (9)	0.002 (9)
C7	0.081 (18)	0.16 (3)	0.042 (13)	0.10 (2)	−0.002 (12)	−0.011 (15)
C5	0.028 (9)	0.048 (12)	0.041 (10)	0.023 (9)	0.008 (8)	−0.007 (9)
C8	0.094 (19)	0.15 (3)	0.041 (12)	0.10 (2)	0.012 (12)	0.024 (14)
C4	0.11 (2)	0.09 (2)	0.042 (14)	0.067 (19)	−0.010 (14)	−0.005 (13)
N15	0.038 (10)	0.100 (16)	0.053 (12)	0.009 (11)	−0.013 (9)	−0.036 (11)

Geometric parameters (Å, º)

Se1—C1	1.88 (2)	N11—H11B	0.8600
Se2—C2	1.83 (3)	N12—H12A	0.8600
Se3—C3	1.828 (19)	N12—H12B	0.8600
Se4—C4	1.87 (3)	N28—H28A	0.8600
Se5—C5	1.864 (18)	N28—H28B	0.8600
Se6—C6	1.882 (18)	N28—C8	1.35 (3)
Se7—C7	1.91 (3)	N25—H25A	0.8600
Se8—C8	1.78 (2)	N25—H25B	0.8600
Se9—C9	1.94 (3)	N25—C5	1.39 (2)
C6—N16	1.27 (2)	N17—H17A	0.8600
C6—N26	1.30 (2)	N17—H17B	0.8600
C2—N21	1.26 (3)	N17—C7	1.26 (3)
C2—N22	1.44 (4)	N18—H18A	0.8600
C9—N19	1.22 (3)	N18—H18B	0.8600
C9—N29	1.18 (3)	N18—C8	1.40 (3)
C3—N23	1.34 (3)	N23—H23A	0.8600
C3—N13	1.34 (3)	N23—H23B	0.8600
C1—N11	1.36 (2)	N14—H14A	0.8600
C1—N12	1.25 (3)	N14—H14B	0.8600
N16—H16A	0.8600	N14—C4	1.33 (3)
N16—H16B	0.8600	N24—H24A	0.8600
N21—H21A	0.8600	N24—H24B	0.8600
N21—H21B	0.8600	N24—C4	1.30 (3)
N19—H19A	0.8600	N27—H27A	0.8600
N19—H19B	0.8600	N27—H27B	0.8600
N29—H29A	0.8600	N27—C7	1.30 (3)
N29—H29B	0.8600	N13—H13A	0.8600
N22—H22A	0.8600	N13—H13B	0.8600
N22—H22B	0.8600	C5—N15	1.26 (2)
N26—H26A	0.8600	N15—H15A	0.8600
N26—H26B	0.8600	N15—H15B	0.8600
N11—H11A	0.8600
N16—C6—Se6	122.6 (15)	C8—N28—H28B	120.0
N16—C6—N26	121.0 (18)	H25A—N25—H25B	120.0
N26—C6—Se6	116.2 (15)	C5—N25—H25A	120.0
N21—C2—Se2	129 (2)	C5—N25—H25B	120.0
N21—C2—N22	115 (3)	H17A—N17—H17B	120.0
N22—C2—Se2	116 (2)	C7—N17—H17A	120.0
N19—C9—Se9	117 (2)	C7—N17—H17B	120.0
N29—C9—Se9	119 (2)	H18A—N18—H18B	120.0
N29—C9—N19	123 (3)	C8—N18—H18A	120.0
N23—C3—Se3	122.2 (16)	C8—N18—H18B	120.0
N13—C3—Se3	123.0 (17)	C3—N23—H23A	120.0
N13—C3—N23	115 (2)	C3—N23—H23B	120.0
N11—C1—Se1	117.4 (15)	H23A—N23—H23B	120.0
N12—C1—Se1	122.9 (15)	H14A—N14—H14B	120.0
N12—C1—N11	120 (2)	C4—N14—H14A	120.0
C6—N16—H16A	120.0	C4—N14—H14B	120.0
C6—N16—H16B	120.0	H24A—N24—H24B	120.0
H16A—N16—H16B	120.0	C4—N24—H24A	120.0
C2—N21—H21A	120.0	C4—N24—H24B	120.0
C2—N21—H21B	120.0	H27A—N27—H27B	120.0
H21A—N21—H21B	120.0	C7—N27—H27A	120.0
C9—N19—H19A	120.0	C7—N27—H27B	120.0
C9—N19—H19B	120.0	C3—N13—H13A	120.0
H19A—N19—H19B	120.0	C3—N13—H13B	120.0
C9—N29—H29A	120.0	H13A—N13—H13B	120.0
C9—N29—H29B	120.0	N17—C7—Se7	119.0 (19)
H29A—N29—H29B	120.0	N17—C7—N27	123 (3)
C2—N22—H22A	120.0	N27—C7—Se7	117 (2)
C2—N22—H22B	120.0	N25—C5—Se5	116.3 (14)
H22A—N22—H22B	120.0	N15—C5—Se5	125.3 (15)
C6—N26—H26A	120.0	N15—C5—N25	118.0 (17)
C6—N26—H26B	120.0	N28—C8—Se8	126.3 (18)
H26A—N26—H26B	120.0	N28—C8—N18	113 (2)
C1—N11—H11A	120.0	N18—C8—Se8	119.2 (17)
C1—N11—H11B	120.0	N14—C4—Se4	119 (2)
H11A—N11—H11B	120.0	N24—C4—Se4	119 (2)
C1—N12—H12A	120.0	N24—C4—N14	122 (3)
C1—N12—H12B	120.0	C5—N15—H15A	120.0
H12A—N12—H12B	120.0	C5—N15—H15B	120.0
H28A—N28—H28B	120.0	H15A—N15—H15B	120.0
C8—N28—H28A	120.0

Selenourea (phase_alpha_Selenourea_363K)

Crystal data

CH4N2Se	Dx = 2.073 Mg m^−3
Mr = 123.02	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P31	Cell parameters from 3032 reflections
a = 15.3505 (7) Å	θ = 4.0–25.0°
c = 13.0706 (6) Å	µ = 9.30 mm^−1
V = 2667.3 (3) Å^3	T = 363 K
Z = 27	Plate, orange
F(000) = 1566	0.25 × 0.10 × 0.05 mm

Data collection

Xcalibur, Eos diffractometer	8308 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	5097 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 16.1544 pixels mm^-1	θmax = 29.0°, θmin = 3.1°
ω scans	h = −20→20
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −19→19
Tmin = 0.341, Tmax = 0.628	l = −17→17
28681 measured reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0234P)^2 + 30.3829P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.075	(Δ/σ)max < 0.001
wR(F^2) = 0.158	Δρmax = 1.24 e Å^−3
S = 1.04	Δρmin = −1.49 e Å^−3
8308 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
326 parameters	Extinction coefficient: 0.00066 (6)
74 restraints	Absolute structure: Refined as a perfect inversion twin.
Primary atom site location: dual	Absolute structure parameter: 0.5
Hydrogen site location: inferred from neighbouring sites

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component perfect inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	0.30541 (18)	0.35177 (17)	0.09620 (16)	0.0441 (5)
Se2	0.39192 (18)	0.36061 (19)	0.75568 (16)	0.0462 (6)
Se3	0.30515 (17)	0.27170 (17)	0.42827 (17)	0.0440 (5)
Se4	0.6315 (2)	0.6083 (2)	0.70831 (16)	0.0517 (7)
Se5	0.72151 (18)	0.69260 (19)	0.04925 (19)	0.0488 (6)
Se6	0.63483 (18)	0.7015 (2)	0.38288 (15)	0.0447 (6)
Se7	0.73238 (18)	0.37327 (19)	0.46856 (18)	0.0602 (8)
Se8	0.29926 (18)	0.70166 (18)	0.6681 (2)	0.0541 (7)
Se9	1.06947 (18)	1.0326 (2)	0.46569 (19)	0.0621 (7)
C6	0.7412 (16)	0.6750 (17)	0.3864 (16)	0.051 (5)
C2	0.256 (2)	0.317 (2)	0.762 (2)	0.080 (8)
C9	0.927 (2)	0.9884 (18)	0.4593 (18)	0.063 (7)
C3	0.4088 (16)	0.4028 (15)	0.4190 (16)	0.050 (5)
C1	0.3827 (17)	0.2879 (18)	0.0943 (14)	0.047 (5)
N16	0.7993 (14)	0.6882 (15)	0.3098 (13)	0.062 (5)
H16A	0.850736	0.680638	0.317434	0.075*
H16B	0.786600	0.704592	0.251075	0.075*
N21	0.2054 (18)	0.3085 (18)	0.8391 (17)	0.091 (7)
H21A	0.140994	0.280210	0.834725	0.110*
H21B	0.234730	0.330956	0.896995	0.110*
N19	0.8879 (17)	0.997 (2)	0.5357 (19)	0.099 (8)
H19A	0.828288	0.989150	0.532891	0.118*
H19B	0.919644	1.011589	0.592968	0.118*
N29	0.8865 (18)	0.9690 (19)	0.3798 (19)	0.097 (8)
H29A	0.826845	0.960427	0.374393	0.116*
H29B	0.916411	0.963259	0.326837	0.116*
N22	0.202 (2)	0.278 (2)	0.668 (2)	0.138 (11)
H22A	0.137380	0.249933	0.667056	0.165*
H22B	0.233997	0.281912	0.612621	0.165*
N26	0.7613 (15)	0.6499 (16)	0.4760 (15)	0.073 (6)
H26A	0.812956	0.642479	0.483028	0.087*
H26B	0.722875	0.640955	0.527540	0.087*
N11	0.4330 (13)	0.2922 (14)	0.0083 (11)	0.054 (5)
H11A	0.468581	0.263303	0.006003	0.064*
H11B	0.429424	0.323891	−0.044367	0.064*
N12	0.3887 (17)	0.2410 (19)	0.1710 (13)	0.089 (8)
H12A	0.424543	0.212392	0.167861	0.107*
H12B	0.356906	0.237769	0.226360	0.107*
N28	0.3897 (18)	0.6022 (17)	0.7574 (18)	0.083 (6)
H28A	0.430667	0.579436	0.754489	0.099*
H28B	0.358379	0.597885	0.813405	0.099*
N25	0.5304 (12)	0.6228 (15)	0.1308 (13)	0.065 (6)
H25A	0.466078	0.596008	0.128939	0.079*
H25B	0.562759	0.650751	0.186051	0.079*
N17	0.5443 (15)	0.2508 (15)	0.3863 (16)	0.073 (6)
H17A	0.479636	0.219002	0.384177	0.088*
H17B	0.578213	0.255956	0.331972	0.088*
N18	0.4305 (17)	0.6466 (18)	0.5882 (17)	0.089 (7)
H18A	0.469864	0.621968	0.592213	0.107*
H18B	0.425423	0.672346	0.531593	0.107*
N23	0.4687 (16)	0.4486 (16)	0.4974 (15)	0.091 (8)
H23A	0.517152	0.509612	0.491216	0.109*
H23B	0.459224	0.417569	0.554683	0.109*
N14	0.686 (2)	0.799 (3)	0.641 (2)	0.146 (12)
H14A	0.716930	0.863505	0.641830	0.175*
H14B	0.651960	0.766861	0.587578	0.175*
N24	0.741 (2)	0.792 (2)	0.8028 (19)	0.110 (9)
H24A	0.773228	0.856936	0.807757	0.132*
H24B	0.741901	0.756330	0.852707	0.132*
N27	0.543 (2)	0.285 (2)	0.5553 (19)	0.112 (9)
H27A	0.478169	0.253811	0.555973	0.135*
H27B	0.575998	0.312440	0.610351	0.135*
N13	0.4295 (19)	0.4571 (18)	0.3335 (17)	0.100 (8)
H13A	0.479079	0.517817	0.332098	0.120*
H13B	0.393124	0.431351	0.279790	0.120*
C7	0.5905 (18)	0.291 (2)	0.4711 (17)	0.069 (8)
C5	0.5823 (14)	0.6209 (16)	0.0443 (14)	0.041 (5)
C8	0.3744 (16)	0.6447 (17)	0.6739 (18)	0.090 (10)
C4	0.691 (2)	0.749 (2)	0.7195 (17)	0.076 (9)
N15	0.5307 (14)	0.5784 (17)	−0.0361 (15)	0.085 (7)
H15A	0.466425	0.552352	−0.035254	0.102*
H15B	0.560403	0.575918	−0.090884	0.102*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0489 (14)	0.0440 (13)	0.0433 (11)	0.0263 (11)	−0.0029 (10)	0.0034 (10)
Se2	0.0394 (13)	0.0501 (14)	0.0493 (13)	0.0225 (11)	−0.0036 (10)	−0.0010 (10)
Se3	0.0457 (13)	0.0370 (12)	0.0427 (11)	0.0159 (11)	0.0036 (10)	0.0005 (10)
Se4	0.0534 (14)	0.0456 (14)	0.0513 (15)	0.0211 (12)	−0.0053 (11)	−0.0041 (10)
Se5	0.0424 (13)	0.0516 (14)	0.0532 (13)	0.0241 (11)	0.0016 (10)	0.0050 (10)
Se6	0.0483 (13)	0.0499 (13)	0.0462 (13)	0.0323 (11)	−0.0005 (10)	−0.0024 (10)
Se7	0.0426 (14)	0.0557 (15)	0.0598 (16)	0.0076 (11)	0.0003 (11)	0.0066 (11)
Se8	0.0649 (16)	0.0537 (14)	0.0568 (15)	0.0394 (13)	−0.0071 (12)	−0.0056 (11)
Se9	0.0457 (14)	0.0659 (17)	0.0665 (16)	0.0218 (13)	0.0003 (12)	0.0073 (12)
C6	0.054 (13)	0.076 (16)	0.048 (12)	0.051 (13)	0.006 (10)	0.011 (11)
C2	0.081 (9)	0.084 (9)	0.077 (9)	0.042 (6)	0.000 (5)	−0.005 (5)
C9	0.10 (2)	0.058 (15)	0.043 (13)	0.052 (16)	−0.002 (13)	0.005 (11)
C3	0.055 (13)	0.033 (11)	0.042 (11)	0.008 (10)	0.000 (10)	0.007 (9)
C1	0.049 (13)	0.067 (15)	0.025 (10)	0.030 (12)	0.016 (9)	0.004 (9)
N16	0.058 (12)	0.106 (16)	0.045 (10)	0.058 (12)	−0.004 (9)	−0.006 (10)
N21	0.074 (10)	0.116 (12)	0.074 (10)	0.040 (8)	0.010 (8)	0.001 (9)
N19	0.075 (16)	0.15 (2)	0.086 (17)	0.066 (17)	−0.031 (13)	−0.042 (16)
N29	0.083 (11)	0.112 (12)	0.087 (11)	0.042 (9)	−0.014 (9)	0.002 (9)
N22	0.127 (14)	0.161 (15)	0.128 (14)	0.074 (10)	0.001 (10)	−0.007 (10)
N26	0.070 (9)	0.101 (10)	0.076 (10)	0.065 (8)	0.003 (7)	0.007 (8)
N11	0.066 (12)	0.077 (13)	0.034 (9)	0.047 (11)	0.006 (8)	0.015 (8)
N12	0.13 (2)	0.17 (2)	0.034 (10)	0.12 (2)	0.010 (11)	0.018 (13)
N28	0.095 (11)	0.093 (11)	0.072 (10)	0.055 (8)	0.009 (8)	0.012 (8)
N25	0.024 (8)	0.097 (15)	0.060 (12)	0.018 (9)	0.007 (8)	−0.019 (11)
N17	0.054 (9)	0.079 (10)	0.062 (9)	0.016 (7)	−0.002 (7)	−0.017 (8)
N18	0.092 (11)	0.117 (11)	0.081 (10)	0.070 (9)	0.005 (8)	0.011 (8)
N23	0.076 (15)	0.073 (15)	0.060 (13)	−0.010 (12)	0.012 (11)	−0.021 (11)
N14	0.158 (15)	0.129 (15)	0.137 (15)	0.063 (10)	−0.006 (10)	0.003 (10)
N24	0.121 (12)	0.101 (12)	0.099 (12)	0.050 (9)	−0.005 (9)	0.009 (9)
N27	0.096 (12)	0.129 (13)	0.097 (12)	0.046 (9)	0.001 (9)	−0.001 (9)
N13	0.108 (12)	0.080 (11)	0.078 (11)	0.021 (8)	−0.001 (9)	0.005 (9)
C7	0.056 (14)	0.15 (3)	0.046 (12)	0.080 (17)	−0.010 (11)	−0.016 (14)
C5	0.034 (10)	0.055 (13)	0.034 (10)	0.022 (10)	0.010 (8)	−0.003 (9)
C8	0.12 (2)	0.17 (3)	0.046 (14)	0.12 (2)	0.014 (14)	0.020 (16)
C4	0.11 (2)	0.10 (2)	0.039 (14)	0.07 (2)	−0.014 (13)	−0.013 (13)
N15	0.049 (12)	0.102 (17)	0.065 (13)	0.009 (12)	−0.018 (10)	−0.046 (12)

Geometric parameters (Å, º)

Se1—C1	1.88 (2)	N11—H11B	0.8600
Se2—C2	1.85 (3)	N12—H12A	0.8600
Se3—C3	1.842 (19)	N12—H12B	0.8600
Se4—C4	1.89 (3)	N28—H28A	0.8600
Se5—C5	1.852 (19)	N28—H28B	0.8600
Se6—C6	1.869 (19)	N28—C8	1.35 (3)
Se7—C7	1.89 (2)	N25—H25A	0.8600
Se8—C8	1.76 (2)	N25—H25B	0.8600
Se9—C9	1.94 (3)	N25—C5	1.39 (2)
C6—N16	1.29 (2)	N17—H17A	0.8600
C6—N26	1.32 (3)	N17—H17B	0.8600
C2—N21	1.24 (3)	N17—C7	1.29 (3)
C2—N22	1.43 (4)	N18—H18A	0.8600
C9—N19	1.21 (3)	N18—H18B	0.8600
C9—N29	1.17 (3)	N18—C8	1.40 (3)
C3—N23	1.32 (3)	N23—H23A	0.8600
C3—N13	1.33 (3)	N23—H23B	0.8600
C1—N11	1.35 (2)	N14—H14A	0.8600
C1—N12	1.26 (3)	N14—H14B	0.8600
N16—H16A	0.8600	N14—C4	1.31 (4)
N16—H16B	0.8600	N24—H24A	0.8600
N21—H21A	0.8600	N24—H24B	0.8600
N21—H21B	0.8600	N24—C4	1.31 (3)
N19—H19A	0.8600	N27—H27A	0.8600
N19—H19B	0.8600	N27—H27B	0.8600
N29—H29A	0.8600	N27—C7	1.30 (3)
N29—H29B	0.8600	N13—H13A	0.8600
N22—H22A	0.8600	N13—H13B	0.8600
N22—H22B	0.8600	C5—N15	1.28 (2)
N26—H26A	0.8600	N15—H15A	0.8600
N26—H26B	0.8600	N15—H15B	0.8600
N11—H11A	0.8600
N16—C6—Se6	124.0 (15)	C8—N28—H28B	120.0
N16—C6—N26	119.4 (19)	H25A—N25—H25B	120.0
N26—C6—Se6	116.3 (15)	C5—N25—H25A	120.0
N21—C2—Se2	127 (2)	C5—N25—H25B	120.0
N21—C2—N22	117 (3)	H17A—N17—H17B	120.0
N22—C2—Se2	115 (2)	C7—N17—H17A	120.0
N19—C9—Se9	117 (2)	C7—N17—H17B	120.0
N29—C9—Se9	119 (2)	H18A—N18—H18B	120.0
N29—C9—N19	122 (3)	C8—N18—H18A	120.0
N23—C3—Se3	121.5 (16)	C8—N18—H18B	120.0
N23—C3—N13	116 (2)	C3—N23—H23A	120.0
N13—C3—Se3	122.9 (17)	C3—N23—H23B	120.0
N11—C1—Se1	118.7 (15)	H23A—N23—H23B	120.0
N12—C1—Se1	122.1 (15)	H14A—N14—H14B	120.0
N12—C1—N11	119 (2)	C4—N14—H14A	120.0
C6—N16—H16A	120.0	C4—N14—H14B	120.0
C6—N16—H16B	120.0	H24A—N24—H24B	120.0
H16A—N16—H16B	120.0	C4—N24—H24A	120.0
C2—N21—H21A	120.0	C4—N24—H24B	120.0
C2—N21—H21B	120.0	H27A—N27—H27B	120.0
H21A—N21—H21B	120.0	C7—N27—H27A	120.0
C9—N19—H19A	120.0	C7—N27—H27B	120.0
C9—N19—H19B	120.0	C3—N13—H13A	120.0
H19A—N19—H19B	120.0	C3—N13—H13B	120.0
C9—N29—H29A	120.0	H13A—N13—H13B	120.0
C9—N29—H29B	120.0	N17—C7—Se7	118.5 (18)
H29A—N29—H29B	120.0	N17—C7—N27	122 (2)
C2—N22—H22A	120.0	N27—C7—Se7	119 (2)
C2—N22—H22B	120.0	N25—C5—Se5	117.5 (14)
H22A—N22—H22B	120.0	N15—C5—Se5	124.5 (15)
C6—N26—H26A	120.0	N15—C5—N25	117.6 (18)
C6—N26—H26B	120.0	N28—C8—Se8	126.1 (19)
H26A—N26—H26B	120.0	N28—C8—N18	114 (2)
C1—N11—H11A	120.0	N18—C8—Se8	120.1 (19)
C1—N11—H11B	120.0	N14—C4—Se4	118 (2)
H11A—N11—H11B	120.0	N14—C4—N24	124 (3)
C1—N12—H12A	120.0	N24—C4—Se4	118 (2)
C1—N12—H12B	120.0	C5—N15—H15A	120.0
H12A—N12—H12B	120.0	C5—N15—H15B	120.0
H28A—N28—H28B	120.0	H15A—N15—H15B	120.0
C8—N28—H28A	120.0

Selenourea (phase_alpha_Selenourea_373K)

Crystal data

CH4N2Se	Dx = 2.064 Mg m^−3
Mr = 123.02	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P31	Cell parameters from 2933 reflections
a = 15.3619 (8) Å	θ = 4.0–24.5°
c = 13.0768 (6) Å	µ = 9.26 mm^−1
V = 2672.5 (3) Å^3	T = 373 K
Z = 27	Plate, orange
F(000) = 1566	0.25 × 0.10 × 0.05 mm

Data collection

Xcalibur, Eos diffractometer	8325 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	4942 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 16.1544 pixels mm^-1	θmax = 29.0°, θmin = 3.1°
ω scans	h = −20→20
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −19→19
Tmin = 0.342, Tmax = 0.629	l = −17→17
28736 measured reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0297P)^2 + 28.6035P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.075	(Δ/σ)max < 0.001
wR(F^2) = 0.167	Δρmax = 1.21 e Å^−3
S = 1.03	Δρmin = −1.40 e Å^−3
8325 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
326 parameters	Extinction coefficient: 0.00064 (7)
93 restraints	Absolute structure: Refined as a perfect inversion twin.
Primary atom site location: dual	Absolute structure parameter: 0.5
Hydrogen site location: inferred from neighbouring sites

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component perfect inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	0.30529 (18)	0.35184 (17)	0.09602 (16)	0.0456 (6)
Se2	0.39180 (19)	0.36075 (19)	0.75585 (17)	0.0478 (6)
Se3	0.30531 (18)	0.27176 (17)	0.42809 (18)	0.0462 (5)
Se4	0.6316 (2)	0.6082 (2)	0.70857 (16)	0.0539 (7)
Se5	0.72160 (18)	0.6925 (2)	0.04891 (19)	0.0515 (6)
Se6	0.63529 (18)	0.7017 (2)	0.38309 (15)	0.0464 (6)
Se7	0.73244 (18)	0.37281 (19)	0.46814 (19)	0.0631 (8)
Se8	0.29910 (19)	0.70171 (18)	0.6689 (2)	0.0570 (7)
Se9	1.06962 (19)	1.0330 (2)	0.46573 (19)	0.0633 (7)
C6	0.7413 (16)	0.6731 (18)	0.3865 (16)	0.052 (5)
C2	0.258 (2)	0.317 (2)	0.759 (2)	0.086 (9)
C9	0.928 (2)	0.9888 (19)	0.4607 (19)	0.062 (6)
C3	0.4078 (15)	0.4034 (15)	0.4183 (15)	0.050 (5)
C1	0.3821 (17)	0.2896 (17)	0.0939 (14)	0.046 (5)
N16	0.7986 (14)	0.6867 (15)	0.3102 (13)	0.064 (5)
H16A	0.850659	0.680077	0.317416	0.077*
H16B	0.785233	0.702557	0.251531	0.077*
N21	0.2033 (17)	0.3068 (18)	0.8382 (17)	0.091 (7)
H21A	0.139106	0.278179	0.831976	0.109*
H21B	0.230941	0.328639	0.896922	0.109*
N19	0.8867 (17)	0.998 (2)	0.5366 (19)	0.102 (9)
H19A	0.827126	0.989654	0.532053	0.123*
H19B	0.917172	1.012617	0.594593	0.123*
N29	0.8857 (18)	0.9686 (19)	0.381 (2)	0.099 (8)
H29A	0.826182	0.960300	0.376219	0.119*
H29B	0.914656	0.962152	0.327286	0.119*
N22	0.202 (2)	0.277 (2)	0.669 (2)	0.120 (9)
H22A	0.137703	0.249894	0.670120	0.144*
H22B	0.232139	0.280446	0.612142	0.144*
N26	0.7611 (16)	0.6488 (17)	0.4767 (16)	0.079 (6)
H26A	0.812939	0.641997	0.484574	0.095*
H26B	0.722082	0.639712	0.527732	0.095*
N11	0.4327 (13)	0.2925 (14)	0.0081 (12)	0.056 (5)
H11A	0.467553	0.262737	0.006766	0.067*
H11B	0.430029	0.323969	−0.045072	0.067*
N12	0.3893 (15)	0.2411 (16)	0.1708 (16)	0.075 (6)
H12A	0.424983	0.212524	0.166093	0.090*
H12B	0.358319	0.237426	0.226884	0.090*
N28	0.3922 (18)	0.6041 (17)	0.7576 (18)	0.084 (6)
H28A	0.433171	0.581453	0.752890	0.101*
H28B	0.362719	0.600148	0.814742	0.101*
N25	0.5305 (13)	0.6234 (15)	0.1319 (13)	0.069 (6)
H25A	0.466305	0.597828	0.130388	0.083*
H25B	0.563340	0.651026	0.186953	0.083*
N17	0.5450 (16)	0.2494 (16)	0.3852 (16)	0.082 (6)
H17A	0.480395	0.217356	0.382296	0.098*
H17B	0.579622	0.255070	0.331412	0.098*
N18	0.4298 (17)	0.6455 (18)	0.5895 (17)	0.092 (7)
H18A	0.468423	0.620164	0.595183	0.111*
H18B	0.425225	0.669997	0.531921	0.111*
N23	0.4687 (17)	0.4490 (18)	0.4974 (17)	0.089 (7)
H23A	0.518053	0.509383	0.491048	0.107*
H23B	0.458512	0.417966	0.554778	0.107*
N14	0.684 (2)	0.796 (2)	0.642 (2)	0.143 (11)
H14A	0.712467	0.860492	0.643763	0.172*
H14B	0.651476	0.763614	0.588592	0.172*
N24	0.738 (2)	0.792 (2)	0.8034 (19)	0.132 (12)
H24A	0.768184	0.856400	0.809262	0.158*
H24B	0.740100	0.756187	0.852982	0.158*
N27	0.543 (2)	0.284 (2)	0.557 (2)	0.120 (9)
H27A	0.478232	0.253144	0.558486	0.144*
H27B	0.576758	0.312213	0.611357	0.144*
N13	0.4284 (19)	0.4559 (19)	0.3328 (18)	0.108 (8)
H13A	0.478696	0.516148	0.330416	0.129*
H13B	0.391384	0.429898	0.279612	0.129*
C7	0.5900 (17)	0.2893 (18)	0.4706 (17)	0.057 (6)
C5	0.5820 (14)	0.6199 (15)	0.0437 (14)	0.041 (5)
C8	0.3741 (16)	0.6467 (15)	0.6741 (19)	0.068 (6)
C4	0.690 (2)	0.749 (2)	0.7188 (17)	0.079 (9)
N15	0.5299 (15)	0.5780 (17)	−0.0362 (15)	0.089 (8)
H15A	0.465767	0.553230	−0.035027	0.107*
H15B	0.558823	0.574649	−0.091084	0.107*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0503 (14)	0.0451 (13)	0.0460 (12)	0.0272 (12)	−0.0047 (10)	0.0018 (10)
Se2	0.0418 (13)	0.0505 (14)	0.0512 (13)	0.0233 (12)	−0.0040 (10)	−0.0008 (10)
Se3	0.0476 (13)	0.0381 (12)	0.0462 (11)	0.0165 (11)	0.0034 (10)	0.0006 (11)
Se4	0.0560 (15)	0.0483 (15)	0.0530 (16)	0.0227 (12)	−0.0058 (11)	−0.0041 (10)
Se5	0.0443 (13)	0.0560 (15)	0.0550 (13)	0.0258 (12)	0.0024 (11)	0.0065 (11)
Se6	0.0501 (14)	0.0530 (14)	0.0468 (13)	0.0338 (12)	0.0007 (10)	0.0003 (10)
Se7	0.0427 (14)	0.0584 (16)	0.0652 (17)	0.0080 (11)	0.0016 (12)	0.0067 (12)
Se8	0.0693 (17)	0.0582 (15)	0.0585 (15)	0.0431 (14)	−0.0077 (12)	−0.0059 (11)
Se9	0.0468 (14)	0.0666 (17)	0.0685 (16)	0.0224 (13)	0.0002 (12)	0.0066 (12)
C6	0.040 (12)	0.081 (17)	0.050 (12)	0.042 (12)	−0.001 (9)	0.002 (11)
C2	0.087 (10)	0.088 (10)	0.083 (10)	0.045 (6)	0.000 (5)	−0.005 (5)
C9	0.090 (19)	0.062 (15)	0.056 (14)	0.053 (15)	0.001 (13)	0.010 (12)
C3	0.043 (12)	0.039 (11)	0.040 (10)	0.000 (9)	0.002 (9)	0.007 (9)
C1	0.058 (14)	0.064 (14)	0.026 (9)	0.038 (12)	0.018 (9)	0.005 (9)
N16	0.056 (12)	0.107 (16)	0.041 (10)	0.050 (12)	−0.002 (9)	−0.007 (10)
N21	0.073 (10)	0.113 (12)	0.076 (10)	0.038 (8)	0.002 (8)	0.005 (9)
N19	0.078 (16)	0.15 (3)	0.087 (17)	0.064 (17)	−0.030 (13)	−0.045 (17)
N29	0.080 (11)	0.114 (12)	0.091 (12)	0.039 (9)	−0.013 (9)	0.004 (9)
N22	0.106 (13)	0.144 (14)	0.110 (13)	0.064 (10)	0.000 (9)	−0.004 (10)
N26	0.077 (10)	0.105 (11)	0.084 (10)	0.067 (8)	−0.001 (8)	0.003 (8)
N11	0.067 (12)	0.071 (12)	0.040 (9)	0.042 (11)	0.005 (8)	0.009 (9)
N12	0.080 (10)	0.092 (10)	0.068 (9)	0.055 (8)	0.000 (8)	0.008 (8)
N28	0.096 (11)	0.095 (11)	0.075 (10)	0.058 (8)	0.008 (8)	0.009 (8)
N25	0.033 (9)	0.107 (17)	0.052 (11)	0.024 (10)	0.019 (8)	−0.007 (11)
N17	0.066 (10)	0.089 (11)	0.066 (10)	0.021 (8)	−0.003 (8)	−0.016 (8)
N18	0.097 (11)	0.118 (11)	0.085 (11)	0.070 (9)	0.003 (8)	0.011 (8)
N23	0.086 (11)	0.085 (11)	0.074 (10)	0.025 (8)	0.004 (8)	−0.011 (8)
N14	0.157 (15)	0.127 (14)	0.133 (14)	0.061 (10)	−0.006 (10)	0.002 (10)
N24	0.21 (3)	0.10 (2)	0.076 (18)	0.07 (2)	−0.01 (2)	0.019 (16)
N27	0.102 (12)	0.138 (13)	0.110 (13)	0.052 (9)	0.001 (9)	0.001 (10)
N13	0.114 (12)	0.090 (11)	0.085 (11)	0.026 (9)	−0.005 (9)	0.002 (9)
C7	0.053 (7)	0.065 (7)	0.057 (7)	0.032 (5)	−0.001 (5)	−0.001 (5)
C5	0.034 (10)	0.052 (12)	0.033 (9)	0.018 (9)	0.012 (8)	0.003 (9)
C8	0.068 (8)	0.074 (8)	0.068 (8)	0.040 (6)	0.001 (5)	0.004 (5)
C4	0.12 (3)	0.12 (2)	0.035 (13)	0.09 (2)	−0.016 (14)	−0.011 (14)
N15	0.051 (12)	0.107 (18)	0.067 (13)	0.008 (12)	−0.021 (10)	−0.046 (12)

Geometric parameters (Å, º)

Se1—C1	1.85 (2)	N11—H11B	0.8600
Se2—C2	1.81 (3)	N12—H12A	0.8600
Se3—C3	1.844 (19)	N12—H12B	0.8600
Se4—C4	1.88 (3)	N28—H28A	0.8600
Se5—C5	1.859 (18)	N28—H28B	0.8600
Se6—C6	1.888 (19)	N28—C8	1.37 (3)
Se7—C7	1.90 (2)	N25—H25A	0.8600
Se8—C8	1.74 (2)	N25—H25B	0.8600
Se9—C9	1.93 (3)	N25—C5	1.41 (2)
C6—N16	1.28 (2)	N17—H17A	0.8600
C6—N26	1.32 (3)	N17—H17B	0.8600
C2—N21	1.30 (3)	N17—C7	1.29 (3)
C2—N22	1.41 (4)	N18—H18A	0.8600
C9—N19	1.22 (3)	N18—H18B	0.8600
C9—N29	1.19 (3)	N18—C8	1.40 (3)
C3—N23	1.33 (3)	N23—H23A	0.8600
C3—N13	1.32 (3)	N23—H23B	0.8600
C1—N11	1.35 (2)	N14—H14A	0.8600
C1—N12	1.29 (3)	N14—H14B	0.8600
N16—H16A	0.8600	N14—C4	1.27 (3)
N16—H16B	0.8600	N24—H24A	0.8600
N21—H21A	0.8600	N24—H24B	0.8600
N21—H21B	0.8600	N24—C4	1.31 (3)
N19—H19A	0.8600	N27—H27A	0.8600
N19—H19B	0.8600	N27—H27B	0.8600
N29—H29A	0.8600	N27—C7	1.32 (3)
N29—H29B	0.8600	N13—H13A	0.8600
N22—H22A	0.8600	N13—H13B	0.8600
N22—H22B	0.8600	C5—N15	1.28 (2)
N26—H26A	0.8600	N15—H15A	0.8600
N26—H26B	0.8600	N15—H15B	0.8600
N11—H11A	0.8600
N16—C6—Se6	123.2 (16)	C8—N28—H28B	120.0
N16—C6—N26	120.5 (19)	H25A—N25—H25B	120.0
N26—C6—Se6	115.8 (16)	C5—N25—H25A	120.0
N21—C2—Se2	128 (2)	C5—N25—H25B	120.0
N21—C2—N22	113 (3)	H17A—N17—H17B	120.0
N22—C2—Se2	118 (2)	C7—N17—H17A	120.0
N19—C9—Se9	119 (2)	C7—N17—H17B	120.0
N29—C9—Se9	120 (2)	H18A—N18—H18B	120.0
N29—C9—N19	120 (3)	C8—N18—H18A	120.0
N23—C3—Se3	120.8 (17)	C8—N18—H18B	120.0
N13—C3—Se3	122.7 (18)	C3—N23—H23A	120.0
N13—C3—N23	116 (2)	C3—N23—H23B	120.0
N11—C1—Se1	120.0 (15)	H23A—N23—H23B	120.0
N12—C1—Se1	123.1 (15)	H14A—N14—H14B	120.0
N12—C1—N11	116.9 (19)	C4—N14—H14A	120.0
C6—N16—H16A	120.0	C4—N14—H14B	120.0
C6—N16—H16B	120.0	H24A—N24—H24B	120.0
H16A—N16—H16B	120.0	C4—N24—H24A	120.0
C2—N21—H21A	120.0	C4—N24—H24B	120.0
C2—N21—H21B	120.0	H27A—N27—H27B	120.0
H21A—N21—H21B	120.0	C7—N27—H27A	120.0
C9—N19—H19A	120.0	C7—N27—H27B	120.0
C9—N19—H19B	120.0	C3—N13—H13A	120.0
H19A—N19—H19B	120.0	C3—N13—H13B	120.0
C9—N29—H29A	120.0	H13A—N13—H13B	120.0
C9—N29—H29B	120.0	N17—C7—Se7	117.8 (18)
H29A—N29—H29B	120.0	N17—C7—N27	124 (2)
C2—N22—H22A	120.0	N27—C7—Se7	117.7 (19)
C2—N22—H22B	120.0	N25—C5—Se5	116.6 (14)
H22A—N22—H22B	120.0	N15—C5—Se5	125.3 (15)
C6—N26—H26A	120.0	N15—C5—N25	117.6 (18)
C6—N26—H26B	120.0	N28—C8—Se8	127 (2)
H26A—N26—H26B	120.0	N28—C8—N18	111 (2)
C1—N11—H11A	120.0	N18—C8—Se8	122 (2)
C1—N11—H11B	120.0	N14—C4—Se4	118 (2)
H11A—N11—H11B	120.0	N14—C4—N24	124 (3)
C1—N12—H12A	120.0	N24—C4—Se4	118 (2)
C1—N12—H12B	120.0	C5—N15—H15A	120.0
H12A—N12—H12B	120.0	C5—N15—H15B	120.0
H28A—N28—H28B	120.0	H15A—N15—H15B	120.0
C8—N28—H28A	120.0

Selenourea (phase_gamma_Selenourea_383K)

Crystal data

CH4N2Se	Dx = 2.072 Mg m^−3
Mr = 123.02	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P3121	Cell parameters from 1753 reflections
a = 8.8551 (4) Å	θ = 4.1–25.8°
c = 13.0694 (7) Å	µ = 9.29 mm^−1
V = 887.51 (9) Å^3	T = 383 K
Z = 9	Plate, orange
F(000) = 522	0.25 × 0.10 × 0.05 mm

Data collection

Xcalibur, Eos diffractometer	1414 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	1204 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 16.1544 pixels mm^-1	θmax = 28.9°, θmin = 3.1°
ω scans	h = −11→11
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −11→11
Tmin = 0.533, Tmax = 1.000	l = −17→16
6352 measured reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0252P)^2 + 0.2031P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.029	(Δ/σ)max < 0.001
wR(F^2) = 0.059	Δρmax = 0.50 e Å^−3
S = 1.06	Δρmin = −0.27 e Å^−3
1414 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
57 parameters	Extinction coefficient: 0.0035 (5)
0 restraints	Absolute structure: Refined as a perfect inversion twin.
Primary atom site location: dual	Absolute structure parameter: 0.5
Hydrogen site location: inferred from neighbouring sites

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component perfect inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	0.000000	−0.07237 (7)	0.666667	0.0472 (2)
Se2	0.44459 (6)	0.76440 (7)	0.29093 (4)	0.0550 (2)
N11	−0.0398 (9)	0.1921 (7)	0.5830 (4)	0.100 (2)
H11A	−0.039510	0.289393	0.583579	0.120*
H11B	−0.065994	0.131181	0.527897	0.120*
N22	0.2111 (8)	0.4352 (7)	0.2192 (4)	0.106 (2)
H22A	0.124959	0.330394	0.223946	0.127*
H22B	0.269226	0.470393	0.163039	0.127*
C1	0.000000	0.1366 (8)	0.666667	0.054 (2)
N21	0.1637 (9)	0.4845 (8)	0.3811 (4)	0.128 (3)
H21A	0.077928	0.379226	0.384605	0.154*
H21B	0.190066	0.552423	0.433211	0.154*
C2	0.2537 (8)	0.5409 (8)	0.2970 (4)	0.0657 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0564 (6)	0.0425 (3)	0.0472 (3)	0.0282 (3)	0.0021 (4)	0.00106 (18)
Se2	0.0454 (3)	0.0467 (3)	0.0624 (3)	0.0151 (3)	−0.0002 (2)	0.0014 (2)
N11	0.198 (7)	0.074 (4)	0.058 (3)	0.091 (4)	−0.028 (4)	−0.004 (3)
N22	0.123 (5)	0.060 (3)	0.069 (3)	−0.003 (3)	0.000 (3)	−0.011 (3)
C1	0.068 (6)	0.051 (3)	0.048 (4)	0.034 (3)	−0.002 (4)	−0.001 (2)
N21	0.109 (5)	0.093 (5)	0.073 (4)	−0.031 (4)	0.025 (4)	−0.005 (3)
C2	0.066 (4)	0.051 (3)	0.054 (3)	0.009 (3)	0.000 (3)	0.002 (3)

Geometric parameters (Å, º)

Se1—C1	1.851 (8)	N22—H22B	0.8600
Se2—C2	1.854 (6)	N22—C2	1.304 (7)
N11—H11A	0.8600	N21—H21A	0.8600
N11—H11B	0.8600	N21—H21B	0.8600
N11—C1	1.316 (6)	N21—C2	1.302 (7)
N22—H22A	0.8600
H11A—N11—H11B	120.0	N11^i—C1—N11	119.0 (7)
C1—N11—H11A	120.0	H21A—N21—H21B	120.0
C1—N11—H11B	120.0	C2—N21—H21A	120.0
H22A—N22—H22B	120.0	C2—N21—H21B	120.0
C2—N22—H22A	120.0	N22—C2—Se2	121.0 (4)
C2—N22—H22B	120.0	N21—C2—Se2	120.2 (4)
N11—C1—Se1	120.5 (3)	N21—C2—N22	118.8 (6)
N11^i—C1—Se1	120.5 (3)

Symmetry code: (i) −x, −x+y, −z+4/3.

Selenourea (phase_gamma_Selenourea_393K)

Crystal data

CH4N2Se	Dx = 2.069 Mg m^−3
Mr = 123.02	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P3121	Cell parameters from 1699 reflections
a = 8.8607 (4) Å	θ = 4.1–25.0°
c = 13.0716 (7) Å	µ = 9.28 mm^−1
V = 888.78 (9) Å^3	T = 393 K
Z = 9	Plate, orange
F(000) = 522	0.25 × 0.10 × 0.05 mm

Data collection

Xcalibur, Eos diffractometer	1422 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	1182 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 16.1544 pixels mm^-1	θmax = 28.9°, θmin = 3.1°
ω scans	h = −11→11
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −11→11
Tmin = 0.523, Tmax = 1.000	l = −17→16
6391 measured reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0256P)^2 + 0.223P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.029	(Δ/σ)max < 0.001
wR(F^2) = 0.059	Δρmax = 0.51 e Å^−3
S = 1.02	Δρmin = −0.31 e Å^−3
1422 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
57 parameters	Extinction coefficient: 0.0041 (5)
0 restraints	Absolute structure: Refined as a perfect inversion twin.
Primary atom site location: dual	Absolute structure parameter: 0.5
Hydrogen site location: inferred from neighbouring sites

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component perfect inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	0.000000	−0.07230 (7)	0.666667	0.0487 (2)
Se2	0.44461 (7)	0.76430 (7)	0.29075 (4)	0.0571 (2)
N11	−0.0389 (9)	0.1924 (7)	0.5832 (4)	0.103 (2)
H11A	−0.038605	0.289550	0.583825	0.123*
H11B	−0.064628	0.131749	0.527972	0.123*
N22	0.2109 (8)	0.4352 (7)	0.2193 (4)	0.108 (2)
H22A	0.124858	0.330390	0.224446	0.130*
H22B	0.268562	0.469889	0.163076	0.130*
C1	0.000000	0.1365 (9)	0.666667	0.056 (2)
N21	0.1634 (9)	0.4842 (8)	0.3809 (4)	0.131 (3)
H21A	0.078054	0.378805	0.383850	0.158*
H21B	0.188837	0.551443	0.433242	0.158*
C2	0.2540 (8)	0.5419 (8)	0.2973 (4)	0.0676 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0581 (6)	0.0439 (3)	0.0487 (3)	0.0290 (3)	0.0021 (4)	0.00107 (19)
Se2	0.0468 (3)	0.0486 (3)	0.0651 (3)	0.0157 (3)	0.0000 (2)	0.0014 (2)
N11	0.202 (7)	0.076 (4)	0.060 (3)	0.092 (5)	−0.025 (4)	−0.004 (3)
N22	0.124 (5)	0.061 (3)	0.073 (3)	−0.005 (3)	0.002 (3)	−0.010 (3)
C1	0.066 (6)	0.055 (4)	0.050 (4)	0.033 (3)	−0.002 (4)	−0.001 (2)
N21	0.118 (5)	0.091 (4)	0.076 (4)	−0.030 (4)	0.027 (4)	−0.005 (3)
C2	0.069 (4)	0.050 (3)	0.058 (3)	0.010 (3)	−0.002 (3)	0.001 (3)

Geometric parameters (Å, º)

Se1—C1	1.850 (8)	N22—H22B	0.8600
Se2—C2	1.848 (6)	N22—C2	1.311 (7)
N11—H11A	0.8600	N21—H21A	0.8600
N11—H11B	0.8600	N21—H21B	0.8600
N11—C1	1.313 (6)	N21—C2	1.300 (7)
N22—H22A	0.8600
H11A—N11—H11B	120.0	N11^i—C1—N11	118.9 (7)
C1—N11—H11A	120.0	H21A—N21—H21B	120.0
C1—N11—H11B	120.0	C2—N21—H21A	120.0
H22A—N22—H22B	120.0	C2—N21—H21B	120.0
C2—N22—H22A	120.0	N22—C2—Se2	121.0 (4)
C2—N22—H22B	120.0	N21—C2—Se2	120.9 (4)
N11—C1—Se1	120.5 (4)	N21—C2—N22	118.0 (6)
N11^i—C1—Se1	120.5 (4)

Symmetry code: (i) −x, −x+y, −z+4/3.