Influence of chlorine and methyl substituents and their position on the anti­microbial activities and crystal structures of 4-methyl-1,6-di­phenyl­py­rimi­dine-2(1H)-sel­en­one derivatives

Derivatives of 4-methyl-1,6-di­phenyl­py­rimi­dine-2(1H)-sel­en­one show very strong anti­microbial activity. In order to extend the current knowledge about the features responsible for the biological activity, crystal structure analyses are presented for 4-methyl-1-(2-methyl­phen­yl)-6-phenyl­py­rimi­dine-2(1H)-sel­en­one (1), 4-methyl-1-(3-methyl­phen­yl)-6-phenyl­py­rimi­dine-2(1H)-sel­en­one (2), 4-methyl-1-(4-methyl­phen­yl)-6-phenyl­py­rimi­dine-2(1H)-sel­en­one (3) (all C₁₈H₁₆N₂Se) and 1-(4-chloro­phen­yl)-4-methyl-6-phenyl­py­rimi­dine-2(1H)-sel­en­one (4) (C₁₇H₁₃ClN₂Se). Furthermore, the anti­bacterial and anti­fungal activities of these com­pounds were evaluated. All the presented derivatives crystallize in the space group P2₁/c with one mol­ecule in the asymmetric unit. The mol­ecular geometries differ slightly in the mutual orientation of the rings. The packing of mol­ecules in the crystals is dominated by C—H...N and C—H...Se inter­molecular inter­actions. Additionally, in the crystal structure of 4, C—H...Cl inter­molecular inter­actions are observed. The introduction of a methyl or chlorine substituent improves the biological activity, while its position significantly affects biological activity only in case of the chlorine substituent.

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015) for (1); COLLECT (Bruker, 2004) for (2), (3), (4). Cell refinement: CrysAlis PRO (Rigaku OD, 2015) for (1); SCALEPACK (Otwinowski & Minor, 1997) for (2), (3), (4). Data reduction: CrysAlis PRO (Rigaku OD, 2015) for (1); DENZO and SCALEPACK (Otwinowski & Minor, 1997) for (2), (3), (4). Program(s) used to solve structure: SIR2014 (Burla et al., 2015) for (1); SHELXS97 (Sheldrick, 2008) for (2), (3), (4). For all structures, program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

4-Methyl-1-(2-methylphenyl)-6-phenylpyrimidine-2(1H)-selenone (1)

Crystal data

C18H16N2Se	F(000) = 688
Mr = 339.29	Dx = 1.476 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7450 reflections
a = 13.6910 (4) Å	θ = 3.6–28.0°
b = 11.2468 (2) Å	µ = 2.45 mm^−1
c = 10.3665 (2) Å	T = 130 K
β = 106.980 (3)°	Plate, orange
V = 1526.65 (6) Å^3	0.38 × 0.31 × 0.06 mm
Z = 4

Data collection

SuperNova, Dual, Cu at zero, Atlas diffractometer	3683 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	2987 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.047
Detector resolution: 10.3756 pixels mm^-1	θmax = 28.6°, θmin = 3.1°
ω scans	h = −18→18
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015)	k = −14→15
Tmin = 0.447, Tmax = 0.862	l = −13→13
20043 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.085	w = 1/[σ^2(Fo^2) + (0.0329P)^2 + 1.6011P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
3683 reflections	Δρmax = 0.68 e Å^−3
192 parameters	Δρmin = −0.72 e Å^−3

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
C2	0.38994 (18)	−0.0723 (2)	0.5277 (2)	0.0191 (5)
N3	0.45736 (15)	−0.16292 (17)	0.55102 (19)	0.0198 (4)
C4	0.46161 (18)	−0.2338 (2)	0.4502 (2)	0.0206 (5)
C5	0.39539 (18)	−0.2198 (2)	0.3194 (2)	0.0224 (5)
H5	0.400062	−0.271229	0.248753	0.027*
C6	0.32443 (17)	−0.1316 (2)	0.2951 (2)	0.0183 (4)
N1	0.32166 (15)	−0.05678 (16)	0.39949 (18)	0.0180 (4)
C19	0.5409 (2)	−0.3290 (2)	0.4797 (2)	0.0264 (5)
H19A	0.604303	−0.297583	0.467191	0.04*
H19B	0.516919	−0.396065	0.418226	0.04*
H19C	0.553661	−0.355979	0.573062	0.04*
C13	0.25143 (18)	−0.1142 (2)	0.1590 (2)	0.0199 (5)
C18	0.2911 (2)	−0.0874 (2)	0.0531 (2)	0.0259 (5)
H18	0.362654	−0.077337	0.069956	0.031*
C17	0.2264 (2)	−0.0754 (3)	−0.0768 (3)	0.0334 (6)
H17	0.253484	−0.056773	−0.148987	0.04*
C16	0.1227 (2)	−0.0905 (3)	−0.1012 (3)	0.0331 (6)
H16	0.07834	−0.081206	−0.190078	0.04*
C15	0.0829 (2)	−0.1190 (2)	0.0033 (3)	0.0313 (6)
H15	0.011498	−0.130856	−0.014633	0.038*
C14	0.14664 (19)	−0.1305 (2)	0.1334 (3)	0.0257 (5)
H14	0.119101	−0.149345	0.205066	0.031*
C7	0.25398 (18)	0.0458 (2)	0.3714 (2)	0.0198 (5)
C12	0.28024 (19)	0.1391 (2)	0.3008 (2)	0.0243 (5)
H12	0.340745	0.135389	0.273778	0.029*
C11	0.2172 (2)	0.2383 (2)	0.2701 (3)	0.0309 (6)
H11	0.233456	0.302357	0.22037	0.037*
C10	0.1306 (2)	0.2428 (2)	0.3127 (3)	0.0332 (6)
H10	0.087923	0.311099	0.293701	0.04*
C9	0.1055 (2)	0.1487 (2)	0.3826 (3)	0.0305 (6)
H9	0.045705	0.153785	0.41114	0.037*
C8	0.16565 (19)	0.0465 (2)	0.4125 (2)	0.0235 (5)
C20	0.1356 (2)	−0.0561 (2)	0.4856 (3)	0.0327 (6)
H20A	0.180812	−0.123753	0.486266	0.049*
H20B	0.064835	−0.078895	0.439771	0.049*
H20C	0.141407	−0.032575	0.578628	0.049*
Se1	0.39029 (2)	0.03034 (2)	0.66592 (2)	0.02545 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0240 (11)	0.0212 (11)	0.0141 (10)	−0.0042 (9)	0.0088 (9)	0.0000 (9)
N3	0.0248 (10)	0.0216 (10)	0.0141 (9)	−0.0003 (8)	0.0073 (8)	0.0019 (7)
C4	0.0251 (12)	0.0196 (11)	0.0181 (11)	−0.0003 (9)	0.0078 (9)	0.0021 (9)
C5	0.0286 (12)	0.0227 (12)	0.0161 (11)	0.0021 (10)	0.0072 (9)	−0.0033 (9)
C6	0.0211 (11)	0.0209 (11)	0.0145 (10)	−0.0034 (9)	0.0076 (9)	−0.0009 (8)
N1	0.0229 (10)	0.0180 (9)	0.0148 (9)	−0.0006 (8)	0.0082 (8)	−0.0008 (7)
C19	0.0316 (13)	0.0249 (12)	0.0213 (12)	0.0034 (10)	0.0057 (10)	−0.0001 (10)
C13	0.0271 (12)	0.0158 (10)	0.0155 (11)	0.0011 (9)	0.0040 (9)	−0.0025 (8)
C18	0.0268 (12)	0.0307 (13)	0.0204 (12)	0.0016 (11)	0.0073 (10)	−0.0010 (10)
C17	0.0435 (16)	0.0372 (15)	0.0185 (12)	0.0047 (13)	0.0072 (11)	0.0031 (11)
C16	0.0373 (15)	0.0343 (15)	0.0205 (13)	0.0068 (12)	−0.0029 (11)	0.0009 (11)
C15	0.0254 (13)	0.0302 (14)	0.0324 (14)	0.0022 (11)	−0.0010 (11)	−0.0062 (11)
C14	0.0257 (12)	0.0280 (13)	0.0241 (12)	−0.0009 (10)	0.0085 (10)	−0.0039 (10)
C7	0.0227 (11)	0.0206 (11)	0.0152 (11)	−0.0003 (9)	0.0040 (9)	−0.0031 (8)
C12	0.0264 (12)	0.0251 (12)	0.0206 (12)	−0.0028 (10)	0.0056 (10)	−0.0014 (9)
C11	0.0330 (14)	0.0245 (13)	0.0318 (14)	−0.0023 (11)	0.0040 (11)	0.0049 (11)
C10	0.0295 (14)	0.0259 (13)	0.0402 (16)	0.0046 (11)	0.0041 (12)	−0.0005 (11)
C9	0.0254 (13)	0.0326 (14)	0.0336 (14)	0.0041 (11)	0.0087 (11)	−0.0056 (11)
C8	0.0251 (12)	0.0259 (12)	0.0207 (12)	−0.0029 (10)	0.0088 (10)	−0.0050 (9)
C20	0.0332 (14)	0.0349 (14)	0.0368 (15)	−0.0034 (12)	0.0207 (12)	0.0010 (12)
Se1	0.03882 (16)	0.02391 (14)	0.01487 (13)	−0.00015 (11)	0.00981 (10)	−0.00236 (9)

Geometric parameters (Å, º)

C2—N3	1.349 (3)	C18—C17	1.386 (3)
C2—N1	1.395 (3)	C17—C16	1.378 (4)
C2—Se1	1.839 (2)	C16—C15	1.385 (4)
N3—C4	1.329 (3)	C15—C14	1.382 (4)
C4—C5	1.403 (3)	C7—C12	1.385 (3)
C4—C19	1.492 (3)	C7—C8	1.395 (3)
C5—C6	1.360 (3)	C12—C11	1.389 (4)
C6—N1	1.380 (3)	C11—C10	1.382 (4)
C6—C13	1.485 (3)	C10—C9	1.381 (4)
N1—C7	1.455 (3)	C9—C8	1.395 (4)
C13—C18	1.393 (3)	C8—C20	1.503 (4)
C13—C14	1.393 (3)
N3—C2—N1	119.9 (2)	C14—C13—C6	122.2 (2)
N3—C2—Se1	119.28 (16)	C17—C18—C13	120.1 (2)
N1—C2—Se1	120.83 (17)	C16—C17—C18	119.9 (3)
C4—N3—C2	119.8 (2)	C17—C16—C15	120.3 (2)
N3—C4—C5	121.9 (2)	C14—C15—C16	120.3 (2)
N3—C4—C19	117.8 (2)	C15—C14—C13	119.7 (2)
C5—C4—C19	120.3 (2)	C12—C7—C8	122.6 (2)
C6—C5—C4	119.1 (2)	C12—C7—N1	117.3 (2)
C5—C6—N1	118.8 (2)	C8—C7—N1	120.1 (2)
C5—C6—C13	121.2 (2)	C7—C12—C11	119.3 (2)
N1—C6—C13	120.0 (2)	C10—C11—C12	119.4 (2)
C6—N1—C2	120.44 (19)	C9—C10—C11	120.5 (3)
C6—N1—C7	119.22 (19)	C10—C9—C8	121.8 (3)
C2—N1—C7	120.03 (18)	C7—C8—C9	116.4 (2)
C18—C13—C14	119.7 (2)	C7—C8—C20	122.7 (2)
C18—C13—C6	117.9 (2)	C9—C8—C20	120.9 (2)
N1—C2—N3—C4	3.1 (3)	C13—C18—C17—C16	−0.3 (4)
Se1—C2—N3—C4	−176.32 (17)	C18—C17—C16—C15	−0.8 (4)
C2—N3—C4—C5	−2.0 (3)	C17—C16—C15—C14	1.2 (4)
C2—N3—C4—C19	177.1 (2)	C16—C15—C14—C13	−0.6 (4)
N3—C4—C5—C6	−0.3 (4)	C18—C13—C14—C15	−0.5 (4)
C19—C4—C5—C6	−179.4 (2)	C6—C13—C14—C15	−176.6 (2)
C4—C5—C6—N1	1.6 (3)	C6—N1—C7—C12	−71.5 (3)
C4—C5—C6—C13	−179.0 (2)	C2—N1—C7—C12	102.3 (2)
C5—C6—N1—C2	−0.6 (3)	C6—N1—C7—C8	107.2 (3)
C13—C6—N1—C2	−179.9 (2)	C2—N1—C7—C8	−79.1 (3)
C5—C6—N1—C7	173.1 (2)	C8—C7—C12—C11	0.5 (4)
C13—C6—N1—C7	−6.2 (3)	N1—C7—C12—C11	179.1 (2)
N3—C2—N1—C6	−1.8 (3)	C7—C12—C11—C10	1.2 (4)
Se1—C2—N1—C6	177.59 (16)	C12—C11—C10—C9	−1.4 (4)
N3—C2—N1—C7	−175.5 (2)	C11—C10—C9—C8	−0.2 (4)
Se1—C2—N1—C7	3.9 (3)	C12—C7—C8—C9	−2.0 (3)
C5—C6—C13—C18	−61.4 (3)	N1—C7—C8—C9	179.4 (2)
N1—C6—C13—C18	117.9 (2)	C12—C7—C8—C20	178.3 (2)
C5—C6—C13—C14	114.8 (3)	N1—C7—C8—C20	−0.3 (3)
N1—C6—C13—C14	−65.8 (3)	C10—C9—C8—C7	1.8 (4)
C14—C13—C18—C17	0.9 (4)	C10—C9—C8—C20	−178.5 (3)
C6—C13—C18—C17	177.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N3^i	0.95	2.51	3.403 (3)	156
C5—H5···Se1^i	0.95	3.03	3.830 (2)	143
C19—H19B···Se1^i	0.98	3.08	4.005 (3)	158
C19—H19C···Se1^ii	0.98	2.89	3.855 (2)	170

Symmetry codes: (i) x, −y−1/2, z−1/2; (ii) −x+1, y−1/2, −z+3/2.

4-Methyl-1-(3-methylphenyl)-6-phenylpyrimidine-2(1H)-selenone (2)

Crystal data

C18H16N2Se	F(000) = 688
Mr = 339.29	Dx = 1.454 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5719 reflections
a = 8.4770 (7) Å	θ = 1.0–27.5°
b = 19.6180 (15) Å	µ = 2.42 mm^−1
c = 9.8030 (9) Å	T = 100 K
β = 108.025 (5)°	Block, red
V = 1550.2 (2) Å^3	0.39 × 0.12 × 0.09 mm
Z = 4

Data collection

KappaCCD diffractometer	3479 independent reflections
Horizonally mounted graphite crystal monochromator	2550 reflections with I > 2σ(I)
Detector resolution: 9 pixels mm^-1	Rint = 0.119
CCD scans	θmax = 27.4°, θmin = 2.4°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = −10→10
Tmin = 0.760, Tmax = 1	k = −24→25
10897 measured reflections	l = −12→12

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.069	H-atom parameters constrained
wR(F^2) = 0.127	w = 1/[σ^2(Fo^2) + (0.031P)^2 + 4.9629P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
3479 reflections	Δρmax = 1.39 e Å^−3
192 parameters	Δρmin = −0.83 e Å^−3

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
C2	0.4682 (5)	−0.0418 (2)	0.3230 (5)	0.0196 (10)
N1	0.4774 (4)	0.01976 (18)	0.2559 (4)	0.0167 (8)
C6	0.6255 (5)	0.0417 (2)	0.2389 (4)	0.0174 (9)
C5	0.7609 (5)	0.0008 (2)	0.2858 (4)	0.0186 (9)
H5	0.862711	0.014474	0.277746	0.022*
C4	0.7443 (5)	−0.0628 (2)	0.3468 (4)	0.0205 (9)
N3	0.6025 (5)	−0.08355 (18)	0.3626 (4)	0.0196 (8)
C19	0.8902 (6)	−0.1095 (3)	0.3983 (6)	0.0335 (12)
H19A	0.853671	−0.153359	0.419657	0.05*
H19B	0.96786	−0.090829	0.483341	0.05*
H19C	0.942885	−0.114136	0.325079	0.05*
C13	0.6284 (5)	0.1088 (2)	0.1697 (5)	0.0183 (9)
C18	0.5588 (6)	0.1169 (3)	0.0227 (5)	0.0236 (10)
H18	0.510931	0.079898	−0.034525	0.028*
C17	0.5609 (6)	0.1805 (3)	−0.0385 (5)	0.0268 (11)
H170	0.516632	0.18592	−0.13728	0.032*
C16	0.6284 (6)	0.2356 (2)	0.0467 (5)	0.0246 (11)
H160	0.625099	0.278559	0.005577	0.03*
C15	0.7009 (5)	0.2276 (2)	0.1926 (5)	0.0222 (10)
H150	0.748339	0.264773	0.249303	0.027*
C14	0.7027 (5)	0.1639 (2)	0.2544 (5)	0.0204 (10)
H14	0.75363	0.158021	0.352303	0.025*
C7	0.3326 (6)	0.0637 (3)	0.2074 (5)	0.0244 (10)
C12	0.2131 (6)	0.0496 (3)	0.0762 (5)	0.0298 (12)
H12	0.223664	0.012013	0.021893	0.036*
C11	0.0789 (6)	0.0929 (3)	0.0292 (6)	0.0382 (14)
H11	−0.002731	0.084434	−0.057523	0.046*
C10	0.0658 (7)	0.1480 (3)	0.1096 (6)	0.0371 (13)
H10	−0.025477	0.176652	0.076085	0.045*
C9	0.1837 (6)	0.1629 (3)	0.2392 (6)	0.0317 (12)
C8	0.3199 (6)	0.1186 (2)	0.2895 (5)	0.0251 (11)
H8	0.400099	0.12647	0.377242	0.03*
C20	0.1713 (8)	0.2248 (3)	0.3260 (7)	0.0442 (15)
H20A	0.188313	0.2651	0.276822	0.066*
H20B	0.254342	0.222363	0.418227	0.066*
H20C	0.063305	0.226386	0.338266	0.066*
Se1	0.27704 (6)	−0.06709 (2)	0.36013 (5)	0.02394 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.023 (2)	0.016 (2)	0.024 (2)	−0.0063 (19)	0.0135 (19)	−0.0013 (18)
N1	0.0135 (17)	0.0158 (18)	0.0234 (19)	−0.0001 (15)	0.0094 (15)	0.0026 (15)
C6	0.020 (2)	0.018 (2)	0.017 (2)	−0.0060 (19)	0.0109 (18)	−0.0050 (18)
C5	0.017 (2)	0.021 (2)	0.020 (2)	−0.0035 (19)	0.0095 (18)	−0.0023 (19)
C4	0.020 (2)	0.021 (2)	0.021 (2)	0.000 (2)	0.0080 (19)	−0.005 (2)
N3	0.0202 (19)	0.0157 (19)	0.027 (2)	0.0011 (16)	0.0125 (16)	0.0021 (15)
C19	0.022 (3)	0.031 (3)	0.051 (3)	0.009 (2)	0.016 (2)	0.010 (3)
C13	0.017 (2)	0.018 (2)	0.026 (2)	−0.0002 (19)	0.0153 (19)	0.0014 (19)
C18	0.025 (2)	0.024 (2)	0.025 (3)	−0.005 (2)	0.012 (2)	0.000 (2)
C17	0.025 (2)	0.029 (3)	0.028 (3)	0.001 (2)	0.011 (2)	0.008 (2)
C16	0.023 (2)	0.020 (2)	0.036 (3)	0.006 (2)	0.018 (2)	0.010 (2)
C15	0.021 (2)	0.017 (2)	0.033 (3)	−0.0018 (19)	0.014 (2)	−0.005 (2)
C14	0.019 (2)	0.020 (2)	0.026 (2)	−0.0006 (19)	0.0122 (19)	−0.0014 (19)
C7	0.022 (2)	0.025 (2)	0.032 (3)	0.002 (2)	0.017 (2)	0.009 (2)
C12	0.020 (2)	0.038 (3)	0.036 (3)	−0.002 (2)	0.015 (2)	0.005 (2)
C11	0.025 (3)	0.055 (4)	0.037 (3)	0.003 (3)	0.013 (2)	0.014 (3)
C10	0.025 (3)	0.039 (3)	0.048 (3)	0.003 (3)	0.013 (3)	0.020 (3)
C9	0.029 (3)	0.024 (3)	0.053 (3)	0.001 (2)	0.029 (3)	0.006 (2)
C8	0.028 (3)	0.016 (2)	0.038 (3)	0.002 (2)	0.020 (2)	0.007 (2)
C20	0.047 (4)	0.026 (3)	0.065 (4)	0.006 (3)	0.025 (3)	0.000 (3)
Se1	0.0216 (2)	0.0205 (2)	0.0352 (3)	−0.0031 (2)	0.01672 (19)	0.0045 (2)

Geometric parameters (Å, º)

C2—N3	1.358 (6)	C16—C15	1.380 (7)
C2—N1	1.389 (6)	C16—H160	0.93
C2—Se1	1.835 (4)	C15—C14	1.387 (6)
N1—C6	1.386 (5)	C15—H150	0.93
N1—C7	1.453 (6)	C14—H14	0.93
C6—C5	1.359 (6)	C7—C8	1.369 (7)
C6—C13	1.483 (6)	C7—C12	1.397 (7)
C5—C4	1.409 (6)	C12—C11	1.379 (7)
C5—H5	0.93	C12—H12	0.93
C4—N3	1.322 (5)	C11—C10	1.363 (9)
C4—C19	1.496 (6)	C11—H11	0.93
C19—H19A	0.96	C10—C9	1.383 (8)
C19—H19B	0.96	C10—H10	0.93
C19—H19C	0.96	C9—C8	1.407 (7)
C13—C18	1.388 (6)	C9—C20	1.504 (7)
C13—C14	1.389 (6)	C8—H8	0.93
C18—C17	1.387 (7)	C20—H20A	0.96
C18—H18	0.93	C20—H20B	0.96
C17—C16	1.379 (7)	C20—H20C	0.96
C17—H170	0.93
N3—C2—N1	119.6 (3)	C17—C16—H160	119.8
N3—C2—Se1	119.6 (3)	C15—C16—H160	119.8
N1—C2—Se1	120.8 (3)	C16—C15—C14	119.8 (4)
C6—N1—C2	120.9 (4)	C16—C15—H150	120.1
C6—N1—C7	118.8 (3)	C14—C15—H150	120.1
C2—N1—C7	120.3 (3)	C15—C14—C13	119.9 (4)
C5—C6—N1	118.5 (4)	C15—C14—H14	120
C5—C6—C13	123.2 (4)	C13—C14—H14	120
N1—C6—C13	118.3 (4)	C8—C7—C12	122.0 (5)
C6—C5—C4	118.8 (4)	C8—C7—N1	119.1 (4)
C6—C5—H5	120.6	C12—C7—N1	118.9 (4)
C4—C5—H5	120.6	C11—C12—C7	118.3 (5)
N3—C4—C5	122.4 (4)	C11—C12—H12	120.8
N3—C4—C19	117.3 (4)	C7—C12—H12	120.8
C5—C4—C19	120.3 (4)	C10—C11—C12	120.1 (5)
C4—N3—C2	119.5 (4)	C10—C11—H11	119.9
C4—C19—H19A	109.5	C12—C11—H11	119.9
C4—C19—H19B	109.5	C11—C10—C9	122.3 (5)
H19A—C19—H19B	109.5	C11—C10—H10	118.9
C4—C19—H19C	109.5	C9—C10—H10	118.9
H19A—C19—H19C	109.5	C10—C9—C8	118.2 (5)
H19B—C19—H19C	109.5	C10—C9—C20	122.2 (5)
C18—C13—C14	120.0 (4)	C8—C9—C20	119.6 (5)
C18—C13—C6	121.0 (4)	C7—C8—C9	119.1 (5)
C14—C13—C6	119.1 (4)	C7—C8—H8	120.4
C17—C18—C13	119.6 (5)	C9—C8—H8	120.4
C17—C18—H18	120.2	C9—C20—H20A	109.5
C13—C18—H18	120.2	C9—C20—H20B	109.5
C16—C17—C18	120.2 (4)	H20A—C20—H20B	109.5
C16—C17—H170	119.9	C9—C20—H20C	109.5
C18—C17—H170	119.9	H20A—C20—H20C	109.5
C17—C16—C15	120.4 (4)	H20B—C20—H20C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19C···Se1^i	0.96	2.90	3.513 (5)	123
C8—H8···N3^ii	0.93	2.70	3.339 (6)	127

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+1.

4-Methyl-1-(4-methylphenyl)-6-phenylpyrimidine-2(1H)-selenone (3)

Crystal data

C18H16N2Se	F(000) = 688
Mr = 339.29	Dx = 1.439 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6950 reflections
a = 12.2520 (3) Å	θ = 1.0–27.5°
b = 12.2930 (3) Å	µ = 2.39 mm^−1
c = 10.4050 (3) Å	T = 100 K
β = 92.516 (2)°	Red, plate
V = 1565.63 (7) Å^3	0.44 × 0.3 × 0.06 mm
Z = 4

Data collection

KappaCCD diffractometer	3592 independent reflections
Horizonally mounted graphite crystal monochromator	3079 reflections with I > 2σ(I)
Detector resolution: 9 pixels mm^-1	Rint = 0.039
CCD scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = −15→15
Tmin = 0.787, Tmax = 1	k = −15→15
12443 measured reflections	l = −13→13

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)] = 0.027	w = 1/[σ^2(Fo^2) + (0.0347P)^2 + 0.7949P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.07	(Δ/σ)max = 0.003
S = 1.04	Δρmax = 0.41 e Å^−3
3592 reflections	Δρmin = −0.48 e Å^−3
193 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0070 (7)

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
C2	0.37304 (14)	0.07969 (14)	1.02643 (17)	0.0154 (3)
N3	0.43470 (12)	0.16988 (12)	1.04800 (14)	0.0155 (3)
C4	0.44321 (14)	0.24380 (14)	0.95640 (17)	0.0165 (3)
C5	0.38807 (14)	0.23402 (14)	0.83590 (17)	0.0176 (4)
H5	0.392985	0.288498	0.77441	0.021*
C6	0.32701 (14)	0.14286 (14)	0.81069 (17)	0.0160 (3)
N1	0.32041 (12)	0.06545 (12)	0.90634 (14)	0.0146 (3)
C19	0.51761 (15)	0.33849 (15)	0.98494 (19)	0.0222 (4)
H19A	0.514997	0.357354	1.074285	0.033*
H19B	0.494429	0.399556	0.933119	0.033*
H19C	0.59103	0.319142	0.96569	0.033*
C13	0.26777 (14)	0.12843 (15)	0.68435 (17)	0.0172 (3)
C18	0.20152 (15)	0.21321 (16)	0.63847 (18)	0.0206 (4)
H18	0.195429	0.276287	0.686979	0.025*
C17	0.14431 (17)	0.20401 (18)	0.5203 (2)	0.0268 (4)
H17	0.098996	0.260245	0.490831	0.032*
C16	0.15494 (18)	0.11117 (18)	0.4467 (2)	0.0289 (4)
H16	0.115301	0.104095	0.368847	0.035*
C15	0.22485 (19)	0.02865 (17)	0.4892 (2)	0.0285 (4)
H15	0.234411	−0.032346	0.438038	0.034*
C14	0.28035 (17)	0.03678 (16)	0.60742 (19)	0.0232 (4)
H14	0.326375	−0.019238	0.635812	0.028*
C7	0.25721 (15)	−0.03316 (14)	0.88041 (17)	0.0160 (3)
C12	0.14452 (15)	−0.02969 (14)	0.87833 (18)	0.0185 (4)
H12	0.108541	0.033373	0.901897	0.022*
C11	0.08537 (15)	−0.12205 (16)	0.84040 (19)	0.0218 (4)
H11	0.009454	−0.120327	0.839359	0.026*
C10	0.13817 (16)	−0.21688 (16)	0.80404 (19)	0.0221 (4)
C9	0.25194 (16)	−0.21816 (15)	0.8099 (2)	0.0226 (4)
H9	0.288354	−0.281275	0.787425	0.027*
C8	0.31225 (15)	−0.12730 (15)	0.84854 (18)	0.0198 (4)
H8	0.388191	−0.129553	0.852969	0.024*
C20	0.07524 (18)	−0.31604 (17)	0.7572 (2)	0.0316 (5)
H20A	0.117829	−0.355669	0.697648	0.047*
H20B	0.007666	−0.293628	0.715043	0.047*
H20C	0.060255	−0.361791	0.829061	0.047*
Se1	0.35942 (2)	−0.01894 (2)	1.15715 (2)	0.02159 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0164 (8)	0.0142 (8)	0.0159 (8)	0.0012 (6)	0.0022 (6)	−0.0023 (6)
N3	0.0171 (7)	0.0136 (7)	0.0158 (7)	−0.0003 (5)	0.0015 (6)	−0.0019 (6)
C4	0.0164 (8)	0.0144 (8)	0.0187 (9)	0.0008 (6)	0.0027 (7)	−0.0014 (7)
C5	0.0209 (9)	0.0157 (8)	0.0165 (8)	−0.0012 (7)	0.0019 (7)	0.0025 (7)
C6	0.0168 (8)	0.0160 (8)	0.0153 (8)	0.0021 (6)	0.0030 (6)	0.0006 (7)
N1	0.0176 (7)	0.0119 (7)	0.0142 (7)	0.0003 (5)	0.0005 (6)	0.0000 (5)
C19	0.0244 (10)	0.0179 (9)	0.0241 (10)	−0.0058 (7)	−0.0015 (7)	0.0013 (7)
C13	0.0178 (8)	0.0194 (9)	0.0145 (8)	−0.0012 (7)	0.0011 (6)	0.0006 (7)
C18	0.0243 (9)	0.0199 (9)	0.0176 (9)	0.0003 (7)	0.0001 (7)	0.0013 (7)
C17	0.0262 (10)	0.0311 (11)	0.0227 (10)	0.0017 (8)	−0.0054 (8)	0.0069 (8)
C16	0.0322 (11)	0.0373 (12)	0.0166 (9)	−0.0076 (9)	−0.0062 (8)	0.0025 (8)
C15	0.0401 (12)	0.0275 (11)	0.0176 (10)	−0.0034 (9)	−0.0002 (8)	−0.0044 (8)
C14	0.0291 (10)	0.0220 (10)	0.0184 (9)	0.0028 (7)	0.0004 (8)	−0.0012 (7)
C7	0.0198 (9)	0.0129 (8)	0.0151 (8)	−0.0030 (6)	−0.0013 (7)	0.0006 (6)
C12	0.0207 (9)	0.0150 (9)	0.0198 (9)	0.0014 (7)	0.0020 (7)	0.0012 (7)
C11	0.0166 (9)	0.0216 (9)	0.0270 (10)	−0.0017 (7)	−0.0015 (7)	0.0001 (8)
C10	0.0250 (10)	0.0181 (9)	0.0229 (9)	−0.0025 (7)	−0.0033 (7)	−0.0005 (7)
C9	0.0250 (10)	0.0150 (9)	0.0276 (10)	0.0035 (7)	−0.0020 (8)	−0.0039 (7)
C8	0.0185 (9)	0.0183 (9)	0.0224 (9)	0.0015 (7)	−0.0022 (7)	−0.0022 (7)
C20	0.0282 (11)	0.0202 (10)	0.0456 (14)	−0.0044 (8)	−0.0072 (9)	−0.0076 (9)
Se1	0.03395 (13)	0.01578 (11)	0.01504 (11)	−0.00326 (8)	0.00095 (7)	0.00317 (7)

Geometric parameters (Å, º)

C2—N3	1.355 (2)	C16—C15	1.388 (3)
C2—N1	1.392 (2)	C16—H16	0.93
C2—Se1	1.8351 (18)	C15—C14	1.383 (3)
N3—C4	1.324 (2)	C15—H15	0.93
C4—C5	1.403 (3)	C14—H14	0.93
C4—C19	1.500 (2)	C7—C12	1.381 (3)
C5—C6	1.366 (2)	C7—C8	1.387 (2)
C5—H5	0.93	C12—C11	1.395 (3)
C6—N1	1.382 (2)	C12—H12	0.93
C6—C13	1.484 (2)	C11—C10	1.394 (3)
N1—C7	1.457 (2)	C11—H11	0.93
C19—H19A	0.96	C10—C9	1.393 (3)
C19—H19B	0.96	C10—C20	1.512 (3)
C19—H19C	0.96	C9—C8	1.389 (3)
C13—C18	1.392 (3)	C9—H9	0.93
C13—C14	1.394 (3)	C8—H8	0.93
C18—C17	1.393 (3)	C20—H20A	0.96
C18—H18	0.93	C20—H20B	0.96
C17—C16	1.384 (3)	C20—H20C	0.96
C17—H17	0.93
N3—C2—N1	118.99 (15)	C17—C16—H16	120.1
N3—C2—Se1	119.08 (13)	C15—C16—H16	120.1
N1—C2—Se1	121.92 (12)	C14—C15—C16	120.22 (19)
C4—N3—C2	120.22 (16)	C14—C15—H15	119.9
N3—C4—C5	122.30 (16)	C16—C15—H15	119.9
N3—C4—C19	117.15 (16)	C15—C14—C13	120.44 (19)
C5—C4—C19	120.53 (16)	C15—C14—H14	119.8
C6—C5—C4	118.68 (17)	C13—C14—H14	119.8
C6—C5—H5	120.7	C12—C7—C8	121.23 (16)
C4—C5—H5	120.7	C12—C7—N1	120.00 (15)
C5—C6—N1	118.38 (16)	C8—C7—N1	118.58 (16)
C5—C6—C13	120.69 (16)	C7—C12—C11	119.09 (17)
N1—C6—C13	120.92 (15)	C7—C12—H12	120.5
C6—N1—C2	121.37 (15)	C11—C12—H12	120.5
C6—N1—C7	119.14 (15)	C10—C11—C12	121.08 (17)
C2—N1—C7	119.50 (14)	C10—C11—H11	119.5
C4—C19—H19A	109.5	C12—C11—H11	119.5
C4—C19—H19B	109.5	C9—C10—C11	118.24 (17)
H19A—C19—H19B	109.5	C9—C10—C20	120.03 (18)
C4—C19—H19C	109.5	C11—C10—C20	121.73 (18)
H19A—C19—H19C	109.5	C8—C9—C10	121.49 (18)
H19B—C19—H19C	109.5	C8—C9—H9	119.3
C18—C13—C14	119.04 (18)	C10—C9—H9	119.3
C18—C13—C6	117.98 (16)	C7—C8—C9	118.83 (17)
C14—C13—C6	122.89 (17)	C7—C8—H8	120.6
C13—C18—C17	120.33 (18)	C9—C8—H8	120.6
C13—C18—H18	119.8	C10—C20—H20A	109.5
C17—C18—H18	119.8	C10—C20—H20B	109.5
C16—C17—C18	119.96 (19)	H20A—C20—H20B	109.5
C16—C17—H17	120	C10—C20—H20C	109.5
C18—C17—H17	120	H20A—C20—H20C	109.5
C17—C16—C15	119.90 (19)	H20B—C20—H20C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N3^i	0.93	2.49	3.293 (2)	145
C5—H5···Se1^i	0.93	3.10	3.974 (2)	156
C8—H8···N3^ii	0.93	2.41	3.279 (2)	155

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, −y, −z+2.

1-(4-Chlorophenyl)-4-methyl-6-phenylpyrimidine-2(1H)-selenone (4)

Crystal data

C17H13ClN2Se	F(000) = 720
Mr = 359.7	Dx = 1.519 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6956 reflections
a = 13.7780 (2) Å	θ = 1.0–27.5°
b = 11.4050 (2) Å	µ = 2.55 mm^−1
c = 10.4020 (3) Å	T = 100 K
β = 105.828 (1)°	Prism, red
V = 1572.58 (6) Å^3	0.39 × 0.25 × 0.22 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	3593 independent reflections
Horizonally mounted graphite crystal monochromator	3227 reflections with I > 2σ(I)
Detector resolution: 9 pixels mm^-1	Rint = 0.027
CCD scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = −17→17
Tmin = 0.876, Tmax = 1	k = −14→14
12403 measured reflections	l = −12→13

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)] = 0.022	w = 1/[σ^2(Fo^2) + (0.0224P)^2 + 1.1006P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.056	(Δ/σ)max = 0.002
S = 1.05	Δρmax = 0.30 e Å^−3
3593 reflections	Δρmin = −0.35 e Å^−3
192 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0059 (5)

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
N3	0.96317 (10)	0.16230 (12)	1.05526 (13)	0.0153 (3)
C4	0.97265 (12)	0.23172 (14)	0.95698 (16)	0.0162 (3)
C5	0.90930 (12)	0.22187 (14)	0.82610 (16)	0.0174 (3)
H5	0.916405	0.273634	0.757689	0.021*
C6	0.83760 (12)	0.13642 (14)	0.79980 (15)	0.0152 (3)
N1	0.83143 (10)	0.06093 (12)	0.90075 (13)	0.0140 (3)
C2	0.89430 (12)	0.07458 (14)	1.02985 (15)	0.0150 (3)
C19	1.05269 (13)	0.32379 (15)	0.98901 (17)	0.0213 (3)
H19A	1.065433	0.347039	1.08285	0.032*
H19B	1.030304	0.39219	0.931541	0.032*
H19C	1.114852	0.292584	0.973665	0.032*
C13	0.76513 (12)	0.12450 (14)	0.66545 (15)	0.0162 (3)
C18	0.80158 (13)	0.10071 (15)	0.55566 (16)	0.0197 (3)
H18	0.871803	0.089568	0.567525	0.024*
C17	0.73473 (15)	0.09333 (16)	0.42851 (17)	0.0256 (4)
H17	0.759181	0.076517	0.353492	0.031*
C16	0.63272 (15)	0.11054 (17)	0.41178 (18)	0.0276 (4)
H16	0.587301	0.105833	0.324916	0.033*
C15	0.59594 (14)	0.13468 (17)	0.52084 (19)	0.0281 (4)
H15	0.525716	0.146365	0.508493	0.034*
C14	0.66225 (13)	0.14164 (16)	0.64792 (17)	0.0228 (4)
H14	0.637465	0.158074	0.722745	0.027*
C7	0.76596 (12)	−0.04089 (14)	0.86602 (15)	0.0154 (3)
C12	0.79215 (12)	−0.12537 (14)	0.78611 (16)	0.0173 (3)
H12	0.853301	−0.118485	0.761166	0.021*
C11	0.72840 (12)	−0.22056 (14)	0.74242 (17)	0.0197 (3)
H11	0.744807	−0.278802	0.686499	0.024*
C10	0.64068 (13)	−0.22849 (15)	0.78219 (17)	0.0206 (3)
C9	0.61518 (13)	−0.14525 (16)	0.86483 (17)	0.0220 (3)
H9	0.555301	−0.153636	0.892524	0.026*
C8	0.67834 (13)	−0.04950 (15)	0.90652 (16)	0.0197 (3)
H8	0.661738	0.009099	0.961878	0.024*
Se1	0.88616 (2)	−0.02359 (2)	1.16677 (2)	0.01812 (7)
Cl1	0.56019 (3)	−0.34709 (4)	0.72652 (5)	0.02899 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N3	0.0183 (7)	0.0158 (6)	0.0129 (6)	0.0010 (5)	0.0058 (5)	−0.0009 (5)
C4	0.0194 (8)	0.0154 (7)	0.0151 (7)	0.0022 (6)	0.0067 (6)	−0.0005 (6)
C5	0.0237 (8)	0.0156 (7)	0.0135 (7)	0.0006 (6)	0.0064 (6)	0.0024 (6)
C6	0.0183 (8)	0.0160 (7)	0.0122 (7)	0.0031 (6)	0.0055 (6)	0.0003 (6)
N1	0.0166 (6)	0.0145 (6)	0.0118 (6)	0.0001 (5)	0.0052 (5)	0.0001 (5)
C2	0.0174 (8)	0.0156 (7)	0.0128 (7)	0.0029 (6)	0.0058 (6)	−0.0011 (6)
C19	0.0260 (9)	0.0202 (8)	0.0174 (8)	−0.0052 (7)	0.0056 (7)	−0.0008 (6)
C13	0.0213 (8)	0.0141 (7)	0.0128 (7)	0.0005 (6)	0.0041 (6)	0.0014 (6)
C18	0.0235 (8)	0.0209 (8)	0.0153 (8)	−0.0012 (7)	0.0064 (6)	0.0001 (6)
C17	0.0354 (10)	0.0266 (9)	0.0147 (8)	−0.0018 (7)	0.0067 (7)	−0.0020 (7)
C16	0.0346 (10)	0.0261 (9)	0.0164 (8)	0.0004 (8)	−0.0028 (7)	−0.0004 (7)
C15	0.0231 (9)	0.0323 (10)	0.0251 (9)	0.0052 (7)	0.0001 (7)	0.0014 (7)
C14	0.0243 (9)	0.0260 (9)	0.0177 (8)	0.0054 (7)	0.0050 (7)	0.0007 (7)
C7	0.0162 (7)	0.0170 (8)	0.0125 (7)	−0.0001 (6)	0.0031 (6)	0.0019 (6)
C12	0.0166 (7)	0.0177 (8)	0.0182 (8)	0.0014 (6)	0.0057 (6)	0.0018 (6)
C11	0.0203 (8)	0.0165 (8)	0.0219 (8)	0.0016 (6)	0.0049 (6)	−0.0005 (6)
C10	0.0189 (8)	0.0184 (8)	0.0223 (8)	−0.0020 (6)	0.0021 (6)	0.0047 (6)
C9	0.0161 (8)	0.0286 (9)	0.0227 (8)	−0.0010 (7)	0.0074 (7)	0.0042 (7)
C8	0.0200 (8)	0.0241 (8)	0.0163 (8)	0.0019 (6)	0.0073 (6)	0.0004 (6)
Se1	0.02780 (10)	0.01574 (9)	0.01163 (9)	−0.00042 (6)	0.00676 (6)	0.00179 (6)
Cl1	0.0233 (2)	0.0231 (2)	0.0381 (3)	−0.00756 (17)	0.00418 (18)	0.00154 (18)

Geometric parameters (Å, º)

N3—C4	1.327 (2)	C17—C16	1.382 (3)
N3—C2	1.354 (2)	C17—H17	0.95
C4—C5	1.407 (2)	C16—C15	1.390 (3)
C4—C19	1.493 (2)	C16—H16	0.95
C5—C6	1.361 (2)	C15—C14	1.389 (2)
C5—H5	0.95	C15—H15	0.95
C6—N1	1.378 (2)	C14—H14	0.95
C6—C13	1.486 (2)	C7—C12	1.383 (2)
N1—C2	1.394 (2)	C7—C8	1.386 (2)
N1—C7	1.454 (2)	C12—C11	1.392 (2)
C2—Se1	1.8389 (16)	C12—H12	0.95
C19—H19A	0.98	C11—C10	1.383 (2)
C19—H19B	0.98	C11—H11	0.95
C19—H19C	0.98	C10—C9	1.389 (3)
C13—C14	1.393 (2)	C10—Cl1	1.7450 (17)
C13—C18	1.394 (2)	C9—C8	1.390 (2)
C18—C17	1.393 (2)	C9—H9	0.95
C18—H18	0.95	C8—H8	0.95
C4—N3—C2	120.08 (14)	C16—C17—H17	120.1
N3—C4—C5	122.15 (15)	C18—C17—H17	120.1
N3—C4—C19	118.00 (14)	C17—C16—C15	120.65 (16)
C5—C4—C19	119.84 (14)	C17—C16—H16	119.7
C6—C5—C4	118.44 (14)	C15—C16—H16	119.7
C6—C5—H5	120.8	C14—C15—C16	119.75 (18)
C4—C5—H5	120.8	C14—C15—H15	120.1
C5—C6—N1	119.09 (14)	C16—C15—H15	120.1
C5—C6—C13	121.28 (14)	C15—C14—C13	119.89 (17)
N1—C6—C13	119.62 (14)	C15—C14—H14	120.1
C6—N1—C2	120.86 (13)	C13—C14—H14	120.1
C6—N1—C7	118.19 (13)	C12—C7—C8	121.65 (15)
C2—N1—C7	120.59 (13)	C12—C7—N1	117.37 (14)
N3—C2—N1	119.26 (14)	C8—C7—N1	120.91 (14)
N3—C2—Se1	119.08 (11)	C7—C12—C11	119.64 (15)
N1—C2—Se1	121.66 (11)	C7—C12—H12	120.2
C4—C19—H19A	109.5	C11—C12—H12	120.2
C4—C19—H19B	109.5	C10—C11—C12	118.57 (16)
H19A—C19—H19B	109.5	C10—C11—H11	120.7
C4—C19—H19C	109.5	C12—C11—H11	120.7
H19A—C19—H19C	109.5	C11—C10—C9	121.99 (16)
H19B—C19—H19C	109.5	C11—C10—Cl1	118.66 (14)
C14—C13—C18	120.09 (15)	C9—C10—Cl1	119.35 (13)
C14—C13—C6	120.61 (15)	C10—C9—C8	119.18 (15)
C18—C13—C6	119.25 (15)	C10—C9—H9	120.4
C17—C18—C13	119.81 (16)	C8—C9—H9	120.4
C17—C18—H18	120.1	C7—C8—C9	118.94 (16)
C13—C18—H18	120.1	C7—C8—H8	120.5
C16—C17—C18	119.81 (17)	C9—C8—H8	120.5
C2—N3—C4—C5	3.5 (2)	C6—C13—C18—C17	−177.79 (16)
C2—N3—C4—C19	−177.39 (14)	C13—C18—C17—C16	0.5 (3)
N3—C4—C5—C6	−1.4 (2)	C18—C17—C16—C15	−0.3 (3)
C19—C4—C5—C6	179.47 (15)	C17—C16—C15—C14	0.0 (3)
C4—C5—C6—N1	−1.8 (2)	C16—C15—C14—C13	0.0 (3)
C4—C5—C6—C13	177.16 (14)	C18—C13—C14—C15	0.2 (3)
C5—C6—N1—C2	3.0 (2)	C6—C13—C14—C15	177.49 (16)
C13—C6—N1—C2	−175.99 (14)	C6—N1—C7—C12	65.85 (19)
C5—C6—N1—C7	−170.15 (14)	C2—N1—C7—C12	−107.30 (17)
C13—C6—N1—C7	10.9 (2)	C6—N1—C7—C8	−111.15 (17)
C4—N3—C2—N1	−2.3 (2)	C2—N1—C7—C8	75.70 (19)
C4—N3—C2—Se1	177.73 (11)	C8—C7—C12—C11	1.4 (2)
C6—N1—C2—N3	−1.0 (2)	N1—C7—C12—C11	−175.61 (14)
C7—N1—C2—N3	171.99 (14)	C7—C12—C11—C10	−0.9 (2)
C6—N1—C2—Se1	179.03 (11)	C12—C11—C10—C9	−0.6 (3)
C7—N1—C2—Se1	−8.00 (19)	C12—C11—C10—Cl1	179.51 (12)
C5—C6—C13—C14	−115.64 (19)	C11—C10—C9—C8	1.5 (3)
N1—C6—C13—C14	63.3 (2)	Cl1—C10—C9—C8	−178.56 (13)
C5—C6—C13—C18	61.7 (2)	C12—C7—C8—C9	−0.4 (2)
N1—C6—C13—C18	−119.37 (17)	N1—C7—C8—C9	176.47 (14)
C14—C13—C18—C17	−0.4 (3)	C10—C9—C8—C7	−1.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N3^i	0.95	2.47	3.372 (2)	158
C5—H5···Se1^i	0.95	3	3.795 (2)	143
C11—H11···Se1^ii	0.95	3.02	3.846 (2)	146
C14—H14···Cl1^iii	0.95	2.91	3.648 (2)	135
C19—H19A···Se1^iv	0.98	2.91	3.862 (2)	165

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y−1/2, z−1/2; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+2, y+1/2, −z+5/2.