Co-crystals of an organic triseleno­cyanate with ditopic Lewis bases: recurrent chalcogen bond interactions motifs

Organic seleno­cyanates R–Se–CN can act as an amphoteric chalcogen bond (ChB) donor (through the Se atom) and acceptor (through the N atom lone pair). Co-crystallization of tri-s­ubstituted 1,3,5-tris­(seleno­cyanato­methyl)-2,4,6-tri­methyl­benzene (1) is investigated with different ditopic Lewis bases acting as chalcogen bond (ChB) acceptors to investigate the outcome of the competition, as ChB acceptor, between the nitro­gen lone pair of the SeCN group and other Lewis bases involving pyridinyl or carbonyl functions. In the presence of tetra­methyl­pyrazine (TMP), benzo­quinone (BQ) and para-di­nitro­benzene (pDNB) as ditopic Lewis bases, a recurrent oligomeric motif stabilized by six ChB interactions is observed, involving six SeCN groups and the ChB acceptor sites of TMP, BQ and pDNB in the 2:1 adducts (1)₂·TMP, (1)₂·BQ and (1)₂·pDNB.

Computing details

For all structures, data collection: Bruker APEX2 (Bruker, 2014); cell refinement: Bruker APEX2 (Bruker, 2014); data reduction: Bruker APEX2 (Bruker, 2014); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014); molecular graphics: ORTEP for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012).

(1TMP)

Crystal data

C15H15N3Se3·0.5(C8H12N2)	Z = 2
Mr = 542.28	F(000) = 530
Triclinic, P1	Dx = 1.743 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.797 (3) Å	Cell parameters from 6066 reflections
b = 10.560 (3) Å	θ = 2.9–26.0°
c = 10.656 (3) Å	µ = 5.35 mm^−1
α = 87.528 (10)°	T = 296 K
β = 69.844 (8)°	Prism, colorless
γ = 87.528 (9)°	0.13 × 0.04 × 0.02 mm
V = 1033.5 (5) Å^3

Data collection

APEXII, Bruker-AXS diffractometer	2995 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.057
CCD rotation images, thick slices scans	θmax = 27.4°, θmin = 1.9°
Absorption correction: multi-scan [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]	h = −12→11
Tmin = 0.774, Tmax = 0.899	k = −13→13
25685 measured reflections	l = −13→13
4706 independent reflections

Refinement

Refinement on F^2	Primary atom site location: direct - structure invariant direct methods
Least-squares matrix: full	Secondary atom site location: direct - structure invariant direct methods
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.092	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0366P)^2 + 0.8648P] where P = (Fo^2 + 2Fc^2)/3
4706 reflections	(Δ/σ)max = 0.001
240 parameters	Δρmax = 0.70 e Å^−3
0 restraints	Δρmin = −0.52 e Å^−3
0 constraints

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
C1	1.1028 (4)	0.0541 (3)	0.6188 (4)	0.0294 (9)
C2	1.0005 (4)	0.1473 (3)	0.6089 (4)	0.0301 (9)
C3	0.8647 (4)	0.1574 (3)	0.7117 (4)	0.0307 (9)
C4	0.8305 (4)	0.0742 (4)	0.8242 (4)	0.0316 (9)
C5	0.9339 (4)	−0.0186 (3)	0.8325 (4)	0.0313 (9)
C6	1.0712 (4)	−0.0283 (4)	0.7316 (4)	0.0312 (9)
C7	1.2445 (4)	0.0403 (4)	0.5037 (4)	0.0389 (10)
H7A	1.2234	0.0436	0.4211	0.047*
H7B	1.2874	−0.0428	0.5115	0.047*
C8	1.0357 (4)	0.2374 (4)	0.4879 (4)	0.0434 (10)
H8A	1.1349	0.2621	0.4626	0.065*
H8B	0.9723	0.3112	0.5095	0.065*
H8C	1.022	0.1957	0.4149	0.065*
C9	0.7544 (4)	0.2563 (4)	0.7001 (4)	0.0392 (10)
H9A	0.6581	0.2282	0.7533	0.047*
H9B	0.7592	0.2633	0.6076	0.047*
C10	0.6826 (4)	0.0883 (4)	0.9335 (4)	0.0482 (11)
H10A	0.6774	0.0293	1.0059	0.072*
H10B	0.6077	0.0714	0.898	0.072*
H10C	0.6694	0.1731	0.9654	0.072*
C11	0.8979 (4)	−0.1095 (4)	0.9517 (4)	0.0373 (10)
H11A	0.8177	−0.0733	1.0241	0.045*
H11B	0.9812	−0.1184	0.9811	0.045*
C12	1.1824 (4)	−0.1278 (4)	0.7429 (4)	0.0433 (11)
H12A	1.1468	−0.1706	0.8288	0.065*
H12B	1.2719	−0.0879	0.7332	0.065*
H12C	1.1993	−0.1882	0.6739	0.065*
C13	1.3945 (4)	0.1482 (4)	0.6551 (5)	0.0438 (11)
C14	0.8745 (5)	0.3741 (4)	0.8774 (5)	0.0471 (11)
C15	0.7040 (5)	−0.2280 (4)	0.8454 (4)	0.0477 (12)
C16	1.3556 (4)	0.5056 (4)	0.5626 (5)	0.0463 (11)
C17	1.4503 (5)	0.4974 (4)	0.6338 (5)	0.0495 (12)
C18	1.1947 (5)	0.5059 (5)	0.6306 (5)	0.0645 (14)
H18A	1.148	0.5143	0.5649	0.097*
H18B	1.165	0.5758	0.6898	0.097*
H18C	1.1677	0.4278	0.6811	0.097*
C19	1.3974 (6)	0.4993 (6)	0.7839 (5)	0.0805 (17)
H19A	1.3523	0.4206	0.8203	0.121*
H19B	1.3279	0.5681	0.8139	0.121*
H19C	1.4782	0.5104	0.8133	0.121*
N1	1.4041 (5)	0.1377 (5)	0.7626 (5)	0.0769 (14)
N2	0.9312 (5)	0.3468 (4)	0.9517 (5)	0.0692 (12)
N3	0.6192 (5)	−0.2007 (4)	0.7970 (4)	0.0652 (12)
N4	1.4053 (4)	0.5085 (3)	0.4280 (4)	0.0502 (10)
Se1	1.39051 (5)	0.16930 (4)	0.49006 (5)	0.04673 (15)
Se2	0.78128 (5)	0.42823 (4)	0.75911 (5)	0.05066 (15)
Se3	0.84421 (5)	−0.28103 (4)	0.91729 (4)	0.04628 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0269 (19)	0.027 (2)	0.035 (2)	−0.0007 (16)	−0.0106 (16)	−0.0056 (17)
C2	0.030 (2)	0.031 (2)	0.031 (2)	−0.0081 (17)	−0.0104 (16)	−0.0018 (17)
C3	0.029 (2)	0.026 (2)	0.040 (2)	−0.0029 (16)	−0.0154 (17)	−0.0015 (18)
C4	0.0302 (19)	0.030 (2)	0.034 (2)	−0.0069 (17)	−0.0090 (16)	−0.0066 (18)
C5	0.037 (2)	0.026 (2)	0.033 (2)	−0.0069 (17)	−0.0137 (17)	−0.0004 (17)
C6	0.030 (2)	0.028 (2)	0.038 (2)	−0.0050 (16)	−0.0148 (17)	−0.0021 (18)
C7	0.037 (2)	0.033 (2)	0.042 (2)	−0.0030 (18)	−0.0080 (19)	−0.0043 (19)
C8	0.044 (2)	0.046 (3)	0.040 (2)	0.001 (2)	−0.015 (2)	0.008 (2)
C9	0.034 (2)	0.040 (2)	0.047 (3)	−0.0018 (18)	−0.0184 (19)	−0.001 (2)
C10	0.039 (2)	0.049 (3)	0.044 (3)	0.001 (2)	0.000 (2)	0.006 (2)
C11	0.047 (2)	0.030 (2)	0.036 (2)	−0.0021 (18)	−0.0155 (19)	−0.0030 (18)
C12	0.039 (2)	0.038 (2)	0.051 (3)	0.0006 (19)	−0.014 (2)	0.007 (2)
C13	0.030 (2)	0.043 (3)	0.057 (3)	−0.0063 (19)	−0.011 (2)	−0.006 (2)
C14	0.055 (3)	0.034 (3)	0.057 (3)	0.002 (2)	−0.025 (2)	−0.005 (2)
C15	0.051 (3)	0.047 (3)	0.038 (3)	−0.016 (2)	−0.003 (2)	−0.004 (2)
C16	0.035 (2)	0.032 (2)	0.064 (3)	0.0003 (18)	−0.008 (2)	0.007 (2)
C17	0.043 (3)	0.045 (3)	0.056 (3)	−0.002 (2)	−0.012 (2)	0.008 (2)
C18	0.040 (3)	0.065 (3)	0.080 (4)	0.001 (2)	−0.009 (2)	−0.002 (3)
C19	0.060 (3)	0.109 (5)	0.064 (4)	0.004 (3)	−0.012 (3)	0.006 (3)
N1	0.068 (3)	0.098 (4)	0.069 (3)	−0.028 (3)	−0.025 (3)	−0.003 (3)
N2	0.093 (3)	0.053 (3)	0.080 (3)	0.002 (2)	−0.053 (3)	−0.001 (2)
N3	0.059 (3)	0.079 (3)	0.060 (3)	−0.008 (2)	−0.024 (2)	−0.003 (2)
N4	0.040 (2)	0.044 (2)	0.059 (3)	0.0024 (17)	−0.0091 (19)	0.0069 (19)
Se1	0.0380 (2)	0.0469 (3)	0.0507 (3)	−0.0098 (2)	−0.0092 (2)	0.0056 (2)
Se2	0.0595 (3)	0.0351 (3)	0.0643 (3)	0.0101 (2)	−0.0309 (2)	−0.0058 (2)
Se3	0.0597 (3)	0.0320 (2)	0.0470 (3)	−0.0110 (2)	−0.0179 (2)	0.0059 (2)

Geometric parameters (Å, º)

C1—C2	1.402 (5)	C11—Se3	1.991 (4)
C1—C6	1.405 (5)	C11—H11A	0.97
C1—C7	1.509 (5)	C11—H11B	0.97
C2—C3	1.405 (5)	C12—H12A	0.96
C2—C8	1.517 (5)	C12—H12B	0.96
C3—C4	1.407 (5)	C12—H12C	0.96
C3—C9	1.502 (5)	C13—N1	1.181 (6)
C4—C5	1.401 (5)	C13—Se1	1.777 (5)
C4—C10	1.520 (5)	C14—N2	1.134 (5)
C5—C6	1.406 (5)	C14—Se2	1.854 (5)
C5—C11	1.508 (5)	C15—N3	1.141 (6)
C6—C12	1.513 (5)	C15—Se3	1.847 (6)
C7—Se1	1.983 (4)	C16—N4	1.346 (6)
C7—H7A	0.97	C16—C17	1.385 (6)
C7—H7B	0.97	C16—C18	1.490 (6)
C8—H8A	0.96	C17—N4^i	1.339 (5)
C8—H8B	0.96	C17—C19	1.502 (7)
C8—H8C	0.96	C18—H18A	0.96
C9—Se2	2.004 (4)	C18—H18B	0.96
C9—H9A	0.97	C18—H18C	0.96
C9—H9B	0.97	C19—H19A	0.96
C10—H10A	0.96	C19—H19B	0.96
C10—H10B	0.96	C19—H19C	0.96
C10—H10C	0.96	N4—C17^i	1.339 (5)
C2—C1—C6	120.4 (3)	H10A—C10—H10C	109.5
C2—C1—C7	118.8 (3)	H10B—C10—H10C	109.5
C6—C1—C7	120.8 (3)	C5—C11—Se3	114.4 (3)
C1—C2—C3	119.8 (3)	C5—C11—H11A	108.7
C1—C2—C8	120.3 (3)	Se3—C11—H11A	108.7
C3—C2—C8	119.9 (3)	C5—C11—H11B	108.7
C2—C3—C4	120.5 (3)	Se3—C11—H11B	108.7
C2—C3—C9	119.7 (3)	H11A—C11—H11B	107.6
C4—C3—C9	119.9 (3)	C6—C12—H12A	109.5
C5—C4—C3	119.1 (3)	C6—C12—H12B	109.5
C5—C4—C10	122.0 (4)	H12A—C12—H12B	109.5
C3—C4—C10	118.9 (3)	C6—C12—H12C	109.5
C4—C5—C6	121.1 (3)	H12A—C12—H12C	109.5
C4—C5—C11	119.6 (3)	H12B—C12—H12C	109.5
C6—C5—C11	119.3 (3)	N1—C13—Se1	176.3 (4)
C1—C6—C5	119.2 (3)	N2—C14—Se2	176.7 (4)
C1—C6—C12	120.3 (3)	N3—C15—Se3	176.5 (4)
C5—C6—C12	120.5 (3)	N4—C16—C17	121.2 (4)
C1—C7—Se1	115.6 (3)	N4—C16—C18	116.9 (4)
C1—C7—H7A	108.4	C17—C16—C18	121.8 (4)
Se1—C7—H7A	108.4	N4^i—C17—C16	121.5 (4)
C1—C7—H7B	108.4	N4^i—C17—C19	116.4 (4)
Se1—C7—H7B	108.4	C16—C17—C19	122.1 (4)
H7A—C7—H7B	107.4	C16—C18—H18A	109.5
C2—C8—H8A	109.5	C16—C18—H18B	109.5
C2—C8—H8B	109.5	H18A—C18—H18B	109.5
H8A—C8—H8B	109.5	C16—C18—H18C	109.5
C2—C8—H8C	109.5	H18A—C18—H18C	109.5
H8A—C8—H8C	109.5	H18B—C18—H18C	109.5
H8B—C8—H8C	109.5	C17—C19—H19A	109.5
C3—C9—Se2	114.2 (3)	C17—C19—H19B	109.5
C3—C9—H9A	108.7	H19A—C19—H19B	109.5
Se2—C9—H9A	108.7	C17—C19—H19C	109.5
C3—C9—H9B	108.7	H19A—C19—H19C	109.5
Se2—C9—H9B	108.7	H19B—C19—H19C	109.5
H9A—C9—H9B	107.6	C17^i—N4—C16	117.3 (4)
C4—C10—H10A	109.5	C13—Se1—C7	97.41 (18)
C4—C10—H10B	109.5	C14—Se2—C9	97.04 (18)
H10A—C10—H10B	109.5	C15—Se3—C11	96.98 (18)
C4—C10—H10C	109.5
C6—C1—C2—C3	−0.8 (5)	C2—C1—C6—C12	−179.2 (4)
C7—C1—C2—C3	176.6 (3)	C7—C1—C6—C12	3.3 (5)
C6—C1—C2—C8	179.1 (3)	C4—C5—C6—C1	−2.1 (5)
C7—C1—C2—C8	−3.4 (5)	C11—C5—C6—C1	178.1 (3)
C1—C2—C3—C4	−0.2 (5)	C4—C5—C6—C12	179.1 (4)
C8—C2—C3—C4	179.8 (3)	C11—C5—C6—C12	−0.7 (5)
C1—C2—C3—C9	−179.2 (3)	C2—C1—C7—Se1	77.1 (4)
C8—C2—C3—C9	0.8 (5)	C6—C1—C7—Se1	−105.4 (4)
C2—C3—C4—C5	0.1 (5)	C2—C3—C9—Se2	−83.7 (4)
C9—C3—C4—C5	179.1 (3)	C4—C3—C9—Se2	97.3 (4)
C2—C3—C4—C10	179.9 (3)	C4—C5—C11—Se3	101.7 (4)
C9—C3—C4—C10	−1.1 (5)	C6—C5—C11—Se3	−78.4 (4)
C3—C4—C5—C6	1.0 (5)	N4—C16—C17—N4^i	−0.2 (7)
C10—C4—C5—C6	−178.7 (4)	C18—C16—C17—N4^i	177.0 (4)
C3—C4—C5—C11	−179.1 (3)	N4—C16—C17—C19	177.5 (5)
C10—C4—C5—C11	1.1 (6)	C18—C16—C17—C19	−5.3 (7)
C2—C1—C6—C5	2.0 (5)	C17—C16—N4—C17^i	0.2 (7)
C7—C1—C6—C5	−175.4 (3)	C18—C16—N4—C17^i	−177.1 (4)

Symmetry code: (i) −x+3, −y+1, −z+1.

(1BQ)

Crystal data

C15H15N3Se3·0.5(C6H4O2)	Z = 2
Mr = 528.23	F(000) = 512
Triclinic, P1	Dx = 1.781 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.008 (2) Å	Cell parameters from 3951 reflections
b = 10.4345 (19) Å	θ = 2.7–24.6°
c = 10.760 (2) Å	µ = 5.61 mm^−1
α = 93.538 (5)°	T = 296 K
β = 117.528 (5)°	Needle, yellow
γ = 95.282 (5)°	0.28 × 0.02 × 0.01 mm
V = 985.3 (3) Å^3

Data collection

APEXII, Bruker-AXS diffractometer	4486 independent reflections
Radiation source: fine-focus sealed tube	2412 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.088
CCD rotation images, thick slices scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]	h = −12→12
Tmin = 0.874, Tmax = 0.945	k = −13→9
24136 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: direct - structure invariant direct methods
Least-squares matrix: full	Secondary atom site location: direct - structure invariant direct methods
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.140	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0523P)^2 + 1.8613P] where P = (Fo^2 + 2Fc^2)/3
4486 reflections	(Δ/σ)max < 0.001
229 parameters	Δρmax = 0.82 e Å^−3
0 restraints	Δρmin = −0.66 e Å^−3
0 constraints

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
C1	0.2459 (7)	−0.1361 (5)	0.1014 (6)	0.0321 (14)
C2	0.3681 (6)	−0.0463 (5)	0.1990 (6)	0.0340 (14)
C3	0.3457 (7)	0.0362 (5)	0.2937 (6)	0.0338 (14)
C4	0.2058 (7)	0.0294 (5)	0.2918 (6)	0.0348 (14)
C5	0.0830 (6)	−0.0576 (5)	0.1908 (6)	0.0349 (14)
C6	0.1044 (6)	−0.1417 (5)	0.0958 (6)	0.0351 (14)
C7	0.2677 (7)	−0.2239 (6)	−0.0014 (7)	0.0436 (16)
H7A	0.3608	−0.19	−0.0024	0.052*
H7B	0.1842	−0.2221	−0.095	0.052*
C8	0.5219 (7)	−0.0412 (7)	0.2045 (7)	0.0507 (17)
H8A	0.5181	−0.0053	0.1231	0.076*
H8B	0.5488	−0.1272	0.2054	0.076*
H8C	0.5966	0.0121	0.2885	0.076*
C9	0.4780 (7)	0.1338 (5)	0.4028 (7)	0.0404 (15)
H9A	0.5726	0.1083	0.4118	0.048*
H9B	0.4802	0.1311	0.4937	0.048*
C10	0.1824 (8)	0.1204 (6)	0.3930 (7)	0.0491 (17)
H10A	0.2792	0.1548	0.4713	0.074*
H10B	0.1208	0.0739	0.4268	0.074*
H10C	0.1324	0.1902	0.3452	0.074*
C11	−0.0713 (7)	−0.0630 (6)	0.1813 (7)	0.0437 (16)
H11A	−0.1461	−0.0676	0.0827	0.052*
H11B	−0.0758	0.017	0.2292	0.052*
C12	−0.0276 (7)	−0.2393 (6)	−0.0105 (7)	0.0502 (18)
H12A	−0.0014	−0.277	−0.0785	0.075*
H12B	−0.1157	−0.1964	−0.0577	0.075*
H12C	−0.0494	−0.3061	0.0375	0.075*
C13	0.4240 (9)	−0.3722 (7)	0.2222 (9)	0.066 (2)
C14	0.4365 (8)	0.2799 (6)	0.1744 (9)	0.0514 (18)
C15	0.0408 (8)	−0.1809 (7)	0.4401 (9)	0.0529 (19)
C16	−0.0120 (9)	−0.5398 (7)	0.3680 (8)	0.060 (2)
C17	0.1339 (9)	−0.5270 (7)	0.4971 (9)	0.067 (2)
H17	0.2198	−0.5459	0.4908	0.08*
C18	0.1471 (8)	−0.4896 (6)	0.6225 (8)	0.056 (2)
H18	0.2409	−0.482	0.7032	0.067*
N1	0.5095 (9)	−0.3534 (6)	0.3385 (8)	0.091 (3)
N2	0.4193 (7)	0.2576 (7)	0.0607 (8)	0.0695 (18)
N3	0.1399 (8)	−0.1689 (6)	0.5479 (8)	0.073 (2)
O1	−0.0224 (7)	−0.5746 (6)	0.2513 (7)	0.0907 (19)
Se1	0.27892 (10)	−0.40669 (7)	0.03883 (8)	0.0644 (3)
Se2	0.46601 (8)	0.31386 (6)	0.35479 (8)	0.0526 (2)
Se3	−0.12835 (8)	−0.21052 (7)	0.26265 (8)	0.0524 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.040 (4)	0.030 (3)	0.030 (3)	0.006 (3)	0.019 (3)	0.009 (3)
C2	0.031 (3)	0.034 (3)	0.038 (3)	0.010 (3)	0.015 (3)	0.013 (3)
C3	0.038 (4)	0.023 (3)	0.034 (3)	0.003 (2)	0.010 (3)	0.007 (3)
C4	0.036 (4)	0.035 (3)	0.036 (3)	0.007 (3)	0.017 (3)	0.008 (3)
C5	0.033 (3)	0.036 (3)	0.041 (4)	0.011 (3)	0.020 (3)	0.010 (3)
C6	0.033 (4)	0.035 (3)	0.030 (3)	0.002 (3)	0.009 (3)	0.006 (3)
C7	0.048 (4)	0.039 (3)	0.041 (4)	0.007 (3)	0.019 (3)	0.002 (3)
C8	0.041 (4)	0.053 (4)	0.058 (4)	0.001 (3)	0.026 (3)	−0.007 (3)
C9	0.038 (4)	0.032 (3)	0.042 (4)	0.007 (3)	0.011 (3)	0.008 (3)
C10	0.052 (4)	0.051 (4)	0.044 (4)	−0.002 (3)	0.026 (3)	−0.007 (3)
C11	0.043 (4)	0.038 (3)	0.054 (4)	0.009 (3)	0.025 (3)	0.010 (3)
C12	0.032 (4)	0.054 (4)	0.056 (4)	0.003 (3)	0.014 (3)	0.003 (3)
C13	0.062 (5)	0.043 (4)	0.070 (6)	0.006 (4)	0.010 (5)	0.009 (4)
C14	0.055 (5)	0.044 (4)	0.060 (5)	0.010 (3)	0.029 (4)	0.017 (4)
C15	0.042 (4)	0.057 (4)	0.074 (6)	0.008 (3)	0.038 (4)	0.023 (4)
C16	0.063 (5)	0.042 (4)	0.055 (5)	0.003 (3)	0.013 (4)	−0.005 (4)
C17	0.055 (5)	0.057 (5)	0.075 (6)	−0.002 (4)	0.024 (5)	−0.008 (4)
C18	0.038 (4)	0.045 (4)	0.058 (5)	−0.002 (3)	0.003 (4)	0.000 (4)
N1	0.102 (6)	0.059 (4)	0.066 (5)	0.011 (4)	0.001 (4)	0.016 (4)
N2	0.062 (4)	0.081 (5)	0.076 (5)	0.016 (3)	0.038 (4)	0.027 (4)
N3	0.048 (4)	0.073 (5)	0.074 (5)	0.006 (3)	0.008 (4)	0.018 (4)
O1	0.092 (4)	0.099 (5)	0.069 (4)	0.008 (3)	0.031 (4)	−0.015 (4)
Se1	0.0763 (6)	0.0383 (4)	0.0574 (5)	0.0103 (3)	0.0144 (4)	−0.0032 (3)
Se2	0.0525 (5)	0.0330 (4)	0.0600 (5)	−0.0034 (3)	0.0178 (4)	0.0046 (3)
Se3	0.0416 (4)	0.0567 (4)	0.0604 (5)	−0.0011 (3)	0.0259 (4)	0.0125 (3)

Geometric parameters (Å, º)

C1—C6	1.385 (8)	C10—H10B	0.96
C1—C2	1.399 (8)	C10—H10C	0.96
C1—C7	1.498 (8)	C11—Se3	1.982 (6)
C2—C3	1.403 (8)	C11—H11A	0.97
C2—C8	1.509 (8)	C11—H11B	0.97
C3—C4	1.385 (8)	C12—H12A	0.96
C3—C9	1.529 (8)	C12—H12B	0.96
C4—C5	1.398 (8)	C12—H12C	0.96
C4—C10	1.514 (8)	C13—N1	1.134 (9)
C5—C6	1.410 (8)	C13—Se1	1.816 (8)
C5—C11	1.495 (8)	C14—N2	1.159 (9)
C6—C12	1.517 (8)	C14—Se2	1.829 (8)
C7—Se1	1.983 (6)	C15—N3	1.114 (9)
C7—H7A	0.97	C15—Se3	1.857 (9)
C7—H7B	0.97	C16—O1	1.240 (9)
C8—H8A	0.96	C16—C18^i	1.460 (11)
C8—H8B	0.96	C16—C17	1.466 (10)
C8—H8C	0.96	C17—C18	1.323 (10)
C9—Se2	1.978 (6)	C17—H17	0.93
C9—H9A	0.97	C18—C16^i	1.460 (11)
C9—H9B	0.97	C18—H18	0.93
C10—H10A	0.96
C6—C1—C2	120.8 (5)	H9A—C9—H9B	107.7
C6—C1—C7	119.9 (5)	C4—C10—H10A	109.5
C2—C1—C7	119.3 (5)	C4—C10—H10B	109.5
C1—C2—C3	118.7 (5)	H10A—C10—H10B	109.5
C1—C2—C8	120.4 (5)	C4—C10—H10C	109.5
C3—C2—C8	120.9 (5)	H10A—C10—H10C	109.5
C4—C3—C2	121.1 (5)	H10B—C10—H10C	109.5
C4—C3—C9	119.2 (5)	C5—C11—Se3	114.9 (4)
C2—C3—C9	119.7 (5)	C5—C11—H11A	108.5
C3—C4—C5	119.8 (5)	Se3—C11—H11A	108.5
C3—C4—C10	120.6 (5)	C5—C11—H11B	108.5
C5—C4—C10	119.5 (5)	Se3—C11—H11B	108.5
C4—C5—C6	119.6 (5)	H11A—C11—H11B	107.5
C4—C5—C11	121.2 (5)	C6—C12—H12A	109.5
C6—C5—C11	119.2 (5)	C6—C12—H12B	109.5
C1—C6—C5	119.9 (5)	H12A—C12—H12B	109.5
C1—C6—C12	120.5 (5)	C6—C12—H12C	109.5
C5—C6—C12	119.6 (5)	H12A—C12—H12C	109.5
C1—C7—Se1	114.8 (4)	H12B—C12—H12C	109.5
C1—C7—H7A	108.6	N1—C13—Se1	176.6 (9)
Se1—C7—H7A	108.6	N2—C14—Se2	179.2 (7)
C1—C7—H7B	108.6	N3—C15—Se3	176.5 (7)
Se1—C7—H7B	108.6	O1—C16—C18^i	119.7 (7)
H7A—C7—H7B	107.5	O1—C16—C17	121.1 (8)
C2—C8—H8A	109.5	C18^i—C16—C17	119.2 (7)
C2—C8—H8B	109.5	C18—C17—C16	121.9 (8)
H8A—C8—H8B	109.5	C18—C17—H17	119
C2—C8—H8C	109.5	C16—C17—H17	119
H8A—C8—H8C	109.5	C17—C18—C16^i	118.9 (7)
H8B—C8—H8C	109.5	C17—C18—H18	120.6
C3—C9—Se2	113.6 (4)	C16^i—C18—H18	120.6
C3—C9—H9A	108.9	C13—Se1—C7	96.6 (3)
Se2—C9—H9A	108.9	C14—Se2—C9	97.2 (3)
C3—C9—H9B	108.9	C15—Se3—C11	97.3 (3)
Se2—C9—H9B	108.9
C6—C1—C2—C3	1.5 (8)	C7—C1—C6—C5	−178.9 (5)
C7—C1—C2—C3	179.4 (5)	C2—C1—C6—C12	179.9 (5)
C6—C1—C2—C8	179.8 (5)	C7—C1—C6—C12	2.0 (8)
C7—C1—C2—C8	−2.3 (8)	C4—C5—C6—C1	−1.2 (8)
C1—C2—C3—C4	0.1 (8)	C11—C5—C6—C1	178.7 (5)
C8—C2—C3—C4	−178.2 (5)	C4—C5—C6—C12	177.9 (5)
C1—C2—C3—C9	179.1 (5)	C11—C5—C6—C12	−2.2 (8)
C8—C2—C3—C9	0.9 (8)	C6—C1—C7—Se1	−75.7 (6)
C2—C3—C4—C5	−2.3 (8)	C2—C1—C7—Se1	106.4 (5)
C9—C3—C4—C5	178.7 (5)	C4—C3—C9—Se2	−77.2 (6)
C2—C3—C4—C10	−179.0 (5)	C2—C3—C9—Se2	103.8 (5)
C9—C3—C4—C10	2.0 (8)	C4—C5—C11—Se3	−102.8 (6)
C3—C4—C5—C6	2.8 (8)	C6—C5—C11—Se3	77.3 (6)
C10—C4—C5—C6	179.6 (5)	O1—C16—C17—C18	179.7 (7)
C3—C4—C5—C11	−177.1 (5)	C18^i—C16—C17—C18	−0.1 (11)
C10—C4—C5—C11	−0.3 (8)	C16—C17—C18—C16^i	0.1 (11)
C2—C1—C6—C5	−1.0 (8)

Symmetry code: (i) −x, −y−1, −z+1.

(pDNB)

Crystal data

C15H15N3Se3·0.5(C6H4N2O4)	Z = 2
Mr = 558.23	F(000) = 542
Triclinic, P1	Dx = 1.821 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.187 (3) Å	Cell parameters from 4815 reflections
b = 10.415 (2) Å	θ = 2.7–24.5°
c = 11.232 (3) Å	µ = 5.44 mm^−1
α = 75.891 (8)°	T = 296 K
β = 82.213 (9)°	Needle, colorless
γ = 61.753 (8)°	0.31 × 0.03 × 0.01 mm
V = 1017.8 (5) Å^3

Data collection

APEXII, Bruker-AXS diffractometer	4665 independent reflections
Radiation source: fine-focus sealed tube	2903 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
CCD rotation images, thick slices scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]	h = −12→13
Tmin = 0.822, Tmax = 0.947	k = −9→13
16919 measured reflections	l = −14→14

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.106	w = 1/[σ^2(Fo^2) + (0.0466P)^2 + 0.8073P] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max < 0.001
4665 reflections	Δρmax = 1.10 e Å^−3
247 parameters	Δρmin = −0.47 e Å^−3
0 restraints

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
C1	0.7626 (4)	0.3551 (4)	0.6373 (3)	0.0294 (9)
C2	0.8745 (4)	0.2905 (4)	0.5518 (3)	0.0318 (9)
C3	0.8465 (4)	0.2250 (4)	0.4688 (3)	0.0298 (9)
C4	0.7094 (5)	0.2235 (4)	0.4722 (3)	0.0315 (9)
C5	0.5986 (4)	0.2900 (4)	0.5582 (4)	0.0315 (9)
C6	0.6261 (4)	0.3537 (4)	0.6419 (3)	0.0313 (9)
C7	0.7900 (5)	0.4315 (5)	0.7228 (4)	0.0386 (10)
H7A	0.7007	0.5242	0.7272	0.046*
H7B	0.8694	0.4565	0.6876	0.046*
C8	1.0239 (5)	0.2899 (5)	0.5492 (4)	0.0473 (11)
H8A	1.0111	0.3748	0.578	0.071*
H8B	1.0638	0.2944	0.4666	0.071*
H8C	1.0914	0.2004	0.6013	0.071*
C9	0.9653 (5)	0.1547 (5)	0.3778 (4)	0.0401 (10)
H9A	0.9724	0.0585	0.3778	0.048*
H9B	1.06	0.1375	0.4044	0.048*
C10	0.6805 (5)	0.1521 (5)	0.3825 (4)	0.0472 (12)
H10A	0.6227	0.2281	0.316	0.071*
H10B	0.6268	0.0985	0.424	0.071*
H10C	0.7738	0.0846	0.3509	0.071*
C11	0.4483 (5)	0.2965 (5)	0.5572 (4)	0.0396 (10)
H11A	0.4371	0.281	0.4782	0.048*
H11B	0.3726	0.396	0.5642	0.048*
C12	0.5088 (5)	0.4197 (5)	0.7361 (4)	0.0440 (11)
H12A	0.4439	0.5221	0.7023	0.066*
H12B	0.5555	0.4138	0.8073	0.066*
H12C	0.4518	0.3654	0.759	0.066*
C13	0.9562 (8)	0.1316 (6)	0.8556 (5)	0.0750 (18)
C14	0.8938 (5)	0.4509 (6)	0.2443 (4)	0.0458 (11)
C15	0.5742 (6)	−0.0177 (6)	0.6603 (4)	0.0446 (11)
C16	0.4477 (7)	0.1332 (6)	0.0274 (4)	0.0576 (14)
C17	0.5966 (7)	0.0544 (6)	0.0116 (5)	0.0680 (16)
H17	0.661	0.0919	0.0193	0.082*
C18	0.3507 (7)	0.0832 (6)	0.0164 (5)	0.0648 (15)
H18	0.2489	0.1413	0.0276	0.078*
N11	1.0246 (10)	0.0148 (6)	0.8390 (5)	0.141 (3)
N2	0.8630 (5)	0.5639 (5)	0.2635 (4)	0.0625 (12)
N3	0.6727 (5)	−0.1317 (6)	0.6509 (4)	0.0696 (13)
N4	0.3869 (8)	0.2844 (6)	0.0585 (4)	0.0791 (16)
O1	0.2556 (7)	0.3623 (5)	0.0522 (5)	0.1136 (19)
O2	0.4768 (7)	0.3155 (5)	0.0890 (5)	0.1110 (18)
Se1	0.84403 (7)	0.31350 (6)	0.89203 (4)	0.05981 (18)
Se2	0.93243 (6)	0.27375 (5)	0.20684 (4)	0.05169 (17)
Se3	0.40943 (5)	0.15159 (5)	0.68743 (4)	0.04589 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.035 (2)	0.029 (2)	0.023 (2)	−0.0131 (18)	−0.0053 (17)	−0.0053 (16)
C2	0.033 (2)	0.033 (2)	0.029 (2)	−0.0160 (19)	−0.0061 (18)	−0.0028 (17)
C3	0.032 (2)	0.027 (2)	0.025 (2)	−0.0088 (18)	−0.0022 (17)	−0.0042 (16)
C4	0.041 (2)	0.028 (2)	0.027 (2)	−0.0168 (19)	−0.0101 (18)	−0.0008 (17)
C5	0.035 (2)	0.029 (2)	0.030 (2)	−0.0149 (18)	−0.0025 (18)	−0.0030 (17)
C6	0.034 (2)	0.029 (2)	0.027 (2)	−0.0112 (18)	−0.0018 (17)	−0.0027 (17)
C7	0.049 (3)	0.041 (2)	0.029 (2)	−0.022 (2)	−0.0018 (19)	−0.0076 (19)
C8	0.035 (3)	0.062 (3)	0.050 (3)	−0.023 (2)	0.001 (2)	−0.020 (2)
C9	0.042 (3)	0.039 (2)	0.032 (2)	−0.012 (2)	−0.0008 (19)	−0.0120 (19)
C10	0.057 (3)	0.051 (3)	0.046 (3)	−0.030 (2)	0.001 (2)	−0.021 (2)
C11	0.044 (3)	0.042 (2)	0.033 (2)	−0.021 (2)	−0.0069 (19)	−0.0019 (19)
C12	0.040 (3)	0.048 (3)	0.047 (3)	−0.018 (2)	0.007 (2)	−0.021 (2)
C13	0.124 (5)	0.051 (3)	0.032 (3)	−0.025 (4)	−0.012 (3)	−0.007 (2)
C14	0.042 (3)	0.055 (3)	0.044 (3)	−0.026 (2)	0.001 (2)	−0.009 (2)
C15	0.042 (3)	0.053 (3)	0.043 (3)	−0.028 (3)	0.002 (2)	−0.007 (2)
C16	0.089 (4)	0.051 (3)	0.036 (3)	−0.036 (3)	0.011 (3)	−0.014 (2)
C17	0.090 (5)	0.075 (4)	0.052 (3)	−0.050 (4)	0.009 (3)	−0.017 (3)
C18	0.073 (4)	0.059 (3)	0.050 (3)	−0.019 (3)	0.012 (3)	−0.022 (3)
N11	0.258 (9)	0.049 (3)	0.056 (4)	−0.017 (4)	−0.014 (4)	−0.017 (3)
N2	0.059 (3)	0.058 (3)	0.079 (3)	−0.031 (2)	−0.002 (2)	−0.019 (2)
N3	0.059 (3)	0.072 (3)	0.070 (3)	−0.028 (3)	0.012 (2)	−0.014 (3)
N4	0.122 (5)	0.057 (3)	0.050 (3)	−0.035 (4)	0.015 (3)	−0.019 (3)
O1	0.133 (5)	0.060 (3)	0.114 (4)	−0.010 (3)	0.003 (4)	−0.035 (3)
O2	0.166 (5)	0.094 (4)	0.107 (4)	−0.077 (4)	0.020 (4)	−0.055 (3)
Se1	0.0785 (4)	0.0578 (3)	0.0344 (3)	−0.0178 (3)	−0.0103 (2)	−0.0182 (2)
Se2	0.0685 (4)	0.0520 (3)	0.0304 (3)	−0.0231 (3)	0.0065 (2)	−0.0151 (2)
Se3	0.0452 (3)	0.0480 (3)	0.0469 (3)	−0.0255 (2)	0.0043 (2)	−0.0079 (2)

Geometric parameters (Å, º)

C1—C6	1.391 (5)	C10—H10C	0.96
C1—C2	1.402 (5)	C11—Se3	1.977 (4)
C1—C7	1.513 (5)	C11—H11A	0.97
C2—C3	1.408 (5)	C11—H11B	0.97
C2—C8	1.516 (6)	C12—H12A	0.96
C3—C4	1.400 (6)	C12—H12B	0.96
C3—C9	1.495 (5)	C12—H12C	0.96
C4—C5	1.406 (5)	C13—N11	1.128 (7)
C4—C10	1.518 (5)	C13—Se1	1.807 (6)
C5—C6	1.399 (5)	C14—N2	1.133 (6)
C5—C11	1.501 (6)	C14—Se2	1.840 (5)
C6—C12	1.502 (5)	C15—N3	1.154 (6)
C7—Se1	1.983 (4)	C15—Se3	1.828 (5)
C7—H7A	0.97	C16—C18	1.347 (8)
C7—H7B	0.97	C16—C17	1.352 (8)
C8—H8A	0.96	C16—N4	1.507 (7)
C8—H8B	0.96	C17—C18^i	1.374 (7)
C8—H8C	0.96	C17—H17	0.93
C9—Se2	1.989 (4)	C18—C17^i	1.373 (7)
C9—H9A	0.97	C18—H18	0.93
C9—H9B	0.97	N4—O1	1.193 (7)
C10—H10A	0.96	N4—O2	1.217 (7)
C10—H10B	0.96
C6—C1—C2	121.0 (3)	C4—C10—H10A	109.5
C6—C1—C7	119.8 (4)	C4—C10—H10B	109.5
C2—C1—C7	119.1 (4)	H10A—C10—H10B	109.5
C1—C2—C3	119.0 (4)	C4—C10—H10C	109.5
C1—C2—C8	120.6 (4)	H10A—C10—H10C	109.5
C3—C2—C8	120.4 (4)	H10B—C10—H10C	109.5
C4—C3—C2	120.5 (3)	C5—C11—Se3	115.8 (3)
C4—C3—C9	120.0 (4)	C5—C11—H11A	108.3
C2—C3—C9	119.6 (4)	Se3—C11—H11A	108.3
C3—C4—C5	119.4 (3)	C5—C11—H11B	108.3
C3—C4—C10	120.0 (4)	Se3—C11—H11B	108.3
C5—C4—C10	120.5 (4)	H11A—C11—H11B	107.4
C6—C5—C4	120.5 (4)	C6—C12—H12A	109.5
C6—C5—C11	120.0 (4)	C6—C12—H12B	109.5
C4—C5—C11	119.6 (4)	H12A—C12—H12B	109.5
C1—C6—C5	119.5 (4)	C6—C12—H12C	109.5
C1—C6—C12	120.5 (4)	H12A—C12—H12C	109.5
C5—C6—C12	119.9 (4)	H12B—C12—H12C	109.5
C1—C7—Se1	115.1 (3)	N11—C13—Se1	176.3 (6)
C1—C7—H7A	108.5	N2—C14—Se2	176.1 (5)
Se1—C7—H7A	108.5	N3—C15—Se3	173.8 (4)
C1—C7—H7B	108.5	C18—C16—C17	123.1 (5)
Se1—C7—H7B	108.5	C18—C16—N4	118.3 (6)
H7A—C7—H7B	107.5	C17—C16—N4	118.6 (6)
C2—C8—H8A	109.5	C16—C17—C18^i	117.5 (5)
C2—C8—H8B	109.5	C16—C17—H17	121.3
H8A—C8—H8B	109.5	C18^i—C17—H17	121.3
C2—C8—H8C	109.5	C16—C18—C17^i	119.4 (5)
H8A—C8—H8C	109.5	C16—C18—H18	120.3
H8B—C8—H8C	109.5	C17^i—C18—H18	120.3
C3—C9—Se2	114.7 (3)	O1—N4—O2	125.8 (6)
C3—C9—H9A	108.6	O1—N4—C16	117.5 (7)
Se2—C9—H9A	108.6	O2—N4—C16	116.7 (6)
C3—C9—H9B	108.6	C13—Se1—C7	98.5 (2)
Se2—C9—H9B	108.6	C14—Se2—C9	96.84 (19)
H9A—C9—H9B	107.6	C15—Se3—C11	98.19 (19)
C6—C1—C2—C3	0.8 (5)	C7—C1—C6—C12	−3.6 (6)
C7—C1—C2—C3	−177.3 (3)	C4—C5—C6—C1	2.0 (6)
C6—C1—C2—C8	−178.8 (4)	C11—C5—C6—C1	−176.1 (3)
C7—C1—C2—C8	3.1 (6)	C4—C5—C6—C12	−177.9 (4)
C1—C2—C3—C4	−0.4 (5)	C11—C5—C6—C12	3.9 (6)
C8—C2—C3—C4	179.1 (4)	C6—C1—C7—Se1	80.4 (4)
C1—C2—C3—C9	−179.6 (3)	C2—C1—C7—Se1	−101.5 (4)
C8—C2—C3—C9	0.0 (6)	C4—C3—C9—Se2	76.3 (4)
C2—C3—C4—C5	0.9 (6)	C2—C3—C9—Se2	−104.6 (4)
C9—C3—C4—C5	−180.0 (3)	C6—C5—C11—Se3	−78.3 (4)
C2—C3—C4—C10	−179.8 (4)	C4—C5—C11—Se3	103.6 (4)
C9—C3—C4—C10	−0.7 (6)	C18—C16—C17—C18^i	−0.3 (9)
C3—C4—C5—C6	−1.7 (6)	N4—C16—C17—C18^i	179.8 (4)
C10—C4—C5—C6	179.0 (4)	C17—C16—C18—C17^i	0.3 (9)
C3—C4—C5—C11	176.5 (3)	N4—C16—C18—C17^i	−179.8 (4)
C10—C4—C5—C11	−2.9 (6)	C18—C16—N4—O1	−12.0 (8)
C2—C1—C6—C5	−1.6 (6)	C17—C16—N4—O1	167.9 (6)
C7—C1—C6—C5	176.5 (3)	C18—C16—N4—O2	167.4 (5)
C2—C1—C6—C12	178.4 (4)	C17—C16—N4—O2	−12.7 (7)

Symmetry code: (i) −x+1, −y, −z.