4-{(4-Chloro-phen-yl)[4-(4-methyl-phen-yl)-1,2,3-selenadiazol-5-yl]meth-yl}-4,5,6,7-tetra-hydro-1,2,3-benzoselenadiazole.

In the title compound, C(22)H(19)ClN(4)Se(2), the mean plane of the non-fused selenadiazole ring forms dihedral angles of 54.20 (16)° and 70.48 (11)°, respectively, with the essentially planar [maximum deviations of 0.025 (5) and 0.009 (2) Å, respectively] methyl-phenyl and chloro-phenyl substituents. The tetra-hydro-1,2,3-benzoselenadiazole group is disordered over two sets of sites with a refined occupancy ratio of 0.802 (5):0.198 (5). In the crystal, weak inter-molecular C-H⋯N inter-actions are observed.

Related literature

For biological applications of 1,2,3-selenadiazole derivatives, see: Kuroda et al. (2001 ▶); El-Bahaie et al. (1990 ▶); El-Kashef et al. (1986 ▶); Plano et al. (2010 ▶); Padmavathi et al. (2002 ▶). For the structures of mono and bis-1,2,3-selenadiazole derivatives, see: Marx et al. (2008 ▶); Boag et al. (2010 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C22H19ClN4Se2

M = 532.78

Monoclinic,

a = 9.7226 (18) Å

b = 12.969 (4) Å

c = 17.690 (3) Å

β = 100.959 (19)°

V = 2189.9 (8) Å3

Z = 4

Mo Kα radiation

μ = 3.52 mm−1

T = 293 K

0.4 × 0.3 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.516, T max = 1.000

8795 measured reflections

3849 independent reflections

2590 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.138

S = 1.04

3849 reflections

255 parameters

293 restraints

H-atom parameters constrained

Δρmax = 0.70 e Å−3

Δρmin = −0.68 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681101751X/lh5230sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101751X/lh5230Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H19ClN4Se2	F(000) = 1056
Mr = 532.78	Dx = 1.616 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2877 reflections
a = 9.7226 (18) Å	θ = 2.7–29.4°
b = 12.969 (4) Å	µ = 3.52 mm−1
c = 17.690 (3) Å	T = 293 K
β = 100.959 (19)°	Block, blue
V = 2189.9 (8) Å3	0.4 × 0.3 × 0.2 mm
Z = 4

Oxford Diffraction Xcalibur Eos diffractometer	3849 independent reflections
Radiation source: fine-focus sealed tube	2590 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 15.9821 pixels mm-1	θmax = 25.0°, θmin = 2.7°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −15→13
Tmin = 0.516, Tmax = 1.000	l = −20→21
8795 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0596P)2 + 0.3633P] where P = (Fo2 + 2Fc2)/3
3849 reflections	(Δ/σ)max = 0.001
255 parameters	Δρmax = 0.70 e Å−3
293 restraints	Δρmin = −0.68 e Å−3

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Se2	1.09476 (5)	0.12061 (4)	0.16057 (3)	0.0585 (2)
Se1A	0.8917 (3)	0.22707 (11)	−0.19037 (8)	0.0718 (5)	0.802 (5)
N1A	1.0459 (4)	0.1859 (6)	−0.1174 (3)	0.0651 (10)	0.802 (5)
N2A	1.0132 (5)	0.1456 (10)	−0.0585 (4)	0.0651 (10)	0.802 (5)
C1A	0.8710 (5)	0.1372 (9)	−0.0608 (4)	0.0550 (7)	0.802 (5)
C2A	0.7819 (4)	0.1715 (6)	−0.1252 (2)	0.0550 (7)	0.802 (5)
C3A	0.6210 (4)	0.1768 (5)	−0.1395 (3)	0.0550 (7)	0.802 (5)
H3A1	0.5816	0.1386	−0.1857	0.066*	0.802 (5)
H3A2	0.5902	0.2478	−0.1464	0.066*	0.802 (5)
C4A	0.5716 (6)	0.1296 (5)	−0.0694 (3)	0.0550 (7)	0.802 (5)
H4A1	0.4790	0.1003	−0.0862	0.066*	0.802 (5)
H4A2	0.5637	0.1841	−0.0330	0.066*	0.802 (5)
C5A	0.6695 (6)	0.0453 (5)	−0.0280 (5)	0.0550 (7)	0.802 (5)
H5A1	0.6280	0.0150	0.0125	0.066*	0.802 (5)
H5A2	0.6802	−0.0087	−0.0644	0.066*	0.802 (5)
C6A	0.8145 (7)	0.0897 (9)	0.0070 (3)	0.0550 (7)	0.802 (5)
H6A	0.8761	0.0329	0.0284	0.066*	0.802 (5)
Se1B	0.9566 (8)	0.2149 (5)	−0.1767 (3)	0.0718 (5)	0.198 (5)
N1B	1.0899 (15)	0.176 (3)	−0.0914 (11)	0.0651 (10)	0.198 (5)
N2B	1.0313 (16)	0.139 (5)	−0.0400 (17)	0.0651 (10)	0.198 (5)
C1B	0.8867 (16)	0.136 (3)	−0.0542 (15)	0.0550 (7)	0.198 (5)
C2B	0.8184 (11)	0.179 (2)	−0.1217 (9)	0.0550 (7)	0.198 (5)
C3B	0.6665 (17)	0.150 (2)	−0.1572 (10)	0.0550 (7)	0.198 (5)
H3B1	0.6636	0.0825	−0.1811	0.066*	0.198 (5)
H3B2	0.6265	0.1999	−0.1961	0.066*	0.198 (5)
C4B	0.584 (2)	0.1489 (19)	−0.0911 (12)	0.0550 (7)	0.198 (5)
H4B1	0.5922	0.2149	−0.0647	0.066*	0.198 (5)
H4B2	0.4856	0.1352	−0.1107	0.066*	0.198 (5)
C5B	0.649 (2)	0.063 (2)	−0.0358 (17)	0.0550 (7)	0.198 (5)
H5B1	0.5952	0.0559	0.0050	0.066*	0.198 (5)
H5B2	0.6416	−0.0022	−0.0637	0.066*	0.198 (5)
C6B	0.803 (2)	0.083 (3)	0.0002 (14)	0.0550 (7)	0.198 (5)
H6B	0.8495	0.0184	0.0203	0.066*	0.198 (5)
C7	0.8116 (4)	0.1691 (3)	0.0701 (2)	0.0381 (10)
H7	0.7625	0.2297	0.0451	0.046*
Cl1	0.46832 (17)	0.03231 (15)	0.30184 (9)	0.0924 (6)
N3	1.1287 (4)	0.3213 (4)	0.1634 (2)	0.0590 (11)
C8	0.7283 (4)	0.1319 (4)	0.1297 (2)	0.0397 (11)
C14	0.9555 (4)	0.2050 (4)	0.1089 (2)	0.0398 (11)
C15	0.9973 (4)	0.3053 (4)	0.1179 (2)	0.0430 (11)
N4	1.1966 (4)	0.2421 (4)	0.1914 (3)	0.0694 (13)
C12	0.6800 (5)	0.0107 (4)	0.2241 (3)	0.0568 (13)
H12	0.7008	−0.0501	0.2517	0.068*
C16	0.9173 (5)	0.3976 (4)	0.0856 (2)	0.0431 (11)
C19	0.7582 (6)	0.5702 (5)	0.0261 (4)	0.0690 (16)
C9	0.6174 (5)	0.1898 (4)	0.1437 (3)	0.0525 (13)
H9	0.5960	0.2510	0.1166	0.063*
C11	0.5706 (5)	0.0717 (5)	0.2355 (3)	0.0596 (15)
C10	0.5379 (5)	0.1612 (5)	0.1956 (3)	0.0563 (14)
H10	0.4630	0.2016	0.2037	0.068*
C13	0.7581 (5)	0.0413 (4)	0.1711 (2)	0.0507 (12)
H13	0.8325	0.0004	0.1629	0.061*
C17	0.8653 (6)	0.4074 (4)	0.0074 (3)	0.0575 (14)
H17	0.8840	0.3561	−0.0259	0.069*
C18	0.7867 (6)	0.4917 (4)	−0.0218 (3)	0.0696 (16)
H18	0.7521	0.4959	−0.0745	0.084*
C21	0.8923 (6)	0.4772 (4)	0.1331 (3)	0.0576 (13)
H21	0.9291	0.4741	0.1855	0.069*
C20	0.8137 (6)	0.5610 (4)	0.1034 (3)	0.0709 (16)
H20	0.7975	0.6132	0.1367	0.085*
C22	0.6694 (7)	0.6612 (6)	−0.0055 (4)	0.115 (3)
H22A	0.6222	0.6878	0.0333	0.173*
H22B	0.6014	0.6399	−0.0495	0.173*
H22C	0.7280	0.7139	−0.0206	0.173*

	U11	U22	U33	U12	U13	U23
Se2	0.0497 (3)	0.0567 (4)	0.0679 (4)	0.0162 (3)	0.0084 (3)	0.0100 (3)
Se1A	0.0962 (12)	0.0770 (6)	0.0489 (5)	0.0015 (7)	0.0308 (7)	0.0137 (4)
N1A	0.077 (2)	0.060 (3)	0.069 (4)	0.018 (3)	0.038 (2)	0.015 (3)
N2A	0.077 (2)	0.060 (3)	0.069 (4)	0.018 (3)	0.038 (2)	0.015 (3)
C1A	0.0730 (15)	0.0516 (16)	0.0431 (13)	−0.0072 (14)	0.0177 (12)	−0.0051 (10)
C2A	0.0730 (15)	0.0516 (16)	0.0431 (13)	−0.0072 (14)	0.0177 (12)	−0.0051 (10)
C3A	0.0730 (15)	0.0516 (16)	0.0431 (13)	−0.0072 (14)	0.0177 (12)	−0.0051 (10)
C4A	0.0730 (15)	0.0516 (16)	0.0431 (13)	−0.0072 (14)	0.0177 (12)	−0.0051 (10)
C5A	0.0730 (15)	0.0516 (16)	0.0431 (13)	−0.0072 (14)	0.0177 (12)	−0.0051 (10)
C6A	0.0730 (15)	0.0516 (16)	0.0431 (13)	−0.0072 (14)	0.0177 (12)	−0.0051 (10)
Se1B	0.0962 (12)	0.0770 (6)	0.0489 (5)	0.0015 (7)	0.0308 (7)	0.0137 (4)
N1B	0.077 (2)	0.060 (3)	0.069 (4)	0.018 (3)	0.038 (2)	0.015 (3)
N2B	0.077 (2)	0.060 (3)	0.069 (4)	0.018 (3)	0.038 (2)	0.015 (3)
C1B	0.0730 (15)	0.0516 (16)	0.0431 (13)	−0.0072 (14)	0.0177 (12)	−0.0051 (10)
C2B	0.0730 (15)	0.0516 (16)	0.0431 (13)	−0.0072 (14)	0.0177 (12)	−0.0051 (10)
C3B	0.0730 (15)	0.0516 (16)	0.0431 (13)	−0.0072 (14)	0.0177 (12)	−0.0051 (10)
C4B	0.0730 (15)	0.0516 (16)	0.0431 (13)	−0.0072 (14)	0.0177 (12)	−0.0051 (10)
C5B	0.0730 (15)	0.0516 (16)	0.0431 (13)	−0.0072 (14)	0.0177 (12)	−0.0051 (10)
C6B	0.0730 (15)	0.0516 (16)	0.0431 (13)	−0.0072 (14)	0.0177 (12)	−0.0051 (10)
C7	0.041 (2)	0.038 (3)	0.035 (2)	0.007 (2)	0.009 (2)	0.0016 (19)
Cl1	0.0783 (10)	0.1362 (16)	0.0753 (9)	−0.0163 (10)	0.0468 (8)	−0.0029 (9)
N3	0.052 (2)	0.059 (3)	0.064 (3)	−0.003 (2)	0.004 (2)	−0.001 (2)
C8	0.034 (2)	0.047 (3)	0.038 (2)	0.004 (2)	0.0054 (19)	−0.004 (2)
C14	0.043 (2)	0.040 (3)	0.039 (2)	0.008 (2)	0.014 (2)	0.003 (2)
C15	0.036 (2)	0.048 (3)	0.045 (3)	0.006 (2)	0.010 (2)	−0.001 (2)
N4	0.045 (2)	0.085 (4)	0.076 (3)	0.006 (3)	0.006 (2)	0.008 (3)
C12	0.052 (3)	0.064 (4)	0.056 (3)	0.007 (3)	0.014 (3)	0.015 (3)
C16	0.041 (2)	0.043 (3)	0.048 (3)	0.003 (2)	0.013 (2)	0.002 (2)
C19	0.060 (3)	0.057 (4)	0.094 (4)	0.016 (3)	0.027 (3)	0.020 (3)
C9	0.042 (3)	0.063 (4)	0.052 (3)	0.011 (3)	0.007 (2)	−0.005 (2)
C11	0.042 (3)	0.092 (5)	0.047 (3)	−0.007 (3)	0.014 (2)	−0.009 (3)
C10	0.038 (3)	0.075 (4)	0.057 (3)	0.011 (3)	0.011 (2)	−0.014 (3)
C13	0.044 (3)	0.058 (3)	0.053 (3)	0.015 (3)	0.017 (2)	0.008 (2)
C17	0.070 (3)	0.048 (3)	0.055 (3)	0.000 (3)	0.014 (3)	0.005 (2)
C18	0.079 (4)	0.058 (4)	0.065 (3)	0.006 (4)	−0.003 (3)	0.020 (3)
C21	0.068 (3)	0.050 (3)	0.059 (3)	0.004 (3)	0.025 (3)	0.004 (3)
C20	0.085 (4)	0.058 (4)	0.082 (4)	0.021 (3)	0.046 (3)	0.004 (3)
C22	0.107 (6)	0.104 (6)	0.135 (6)	0.053 (5)	0.021 (5)	0.038 (5)

Se2—C14	1.843 (4)	C5B—H5B2	0.9700
Se2—N4	1.886 (5)	C6B—C7	1.66 (4)
Se1A—C2A	1.8585 (10)	C6B—H6B	0.9800
Se1A—N1A	1.8605 (11)	C7—C14	1.510 (6)
N1A—N2A	1.2601 (10)	C7—C8	1.526 (6)
N2A—C1A	1.3790 (10)	C7—H7	0.9800
C1A—C2A	1.3688 (10)	Cl1—C11	1.753 (5)
C1A—C6A	1.5387 (10)	N3—N4	1.270 (6)
C2A—C3A	1.5385 (10)	N3—C15	1.390 (6)
C3A—C4A	1.5394 (10)	C8—C9	1.375 (6)
C3A—H3A1	0.9700	C8—C13	1.386 (6)
C3A—H3A2	0.9700	C14—C15	1.363 (6)
C4A—C5A	1.5396 (10)	C15—C16	1.482 (6)
C4A—H4A1	0.9700	C12—C11	1.371 (7)
C4A—H4A2	0.9700	C12—C13	1.372 (6)
C5A—C6A	1.5394 (10)	C12—H12	0.9300
C5A—H5A1	0.9700	C16—C21	1.381 (6)
C5A—H5A2	0.9700	C16—C17	1.385 (6)
C6A—C7	1.523 (11)	C19—C20	1.377 (8)
C6A—H6A	0.9800	C19—C18	1.387 (8)
Se1B—C2B	1.8597 (11)	C19—C22	1.506 (8)
Se1B—N1B	1.8602 (11)	C9—C10	1.360 (7)
N1B—N2B	1.2600 (10)	C9—H9	0.9300
N2B—C1B	1.3798 (10)	C11—C10	1.364 (7)
C1B—C2B	1.3698 (10)	C10—H10	0.9300
C1B—C6B	1.5397 (10)	C13—H13	0.9300
C2B—C3B	1.5398 (11)	C17—C18	1.377 (7)
C3B—C4B	1.5399 (10)	C17—H17	0.9300
C3B—H3B1	0.9700	C18—H18	0.9300
C3B—H3B2	0.9700	C21—C20	1.373 (7)
C4B—C5B	1.5398 (10)	C21—H21	0.9300
C4B—H4B1	0.9700	C20—H20	0.9300
C4B—H4B2	0.9700	C22—H22A	0.9600
C5B—C6B	1.5398 (11)	C22—H22B	0.9600
C5B—H5B1	0.9700	C22—H22C	0.9600
C14—Se2—N4	86.7 (2)	C5B—C6B—C7	109 (3)
C2A—Se1A—N1A	86.59 (18)	C1B—C6B—H6B	110.6
N2A—N1A—Se1A	113.4 (3)	C5B—C6B—H6B	110.6
N1A—N2A—C1A	114.7 (4)	C7—C6B—H6B	110.6
C2A—C1A—N2A	118.1 (4)	C14—C7—C6A	113.4 (4)
C2A—C1A—C6A	121.0 (4)	C14—C7—C8	110.6 (3)
N2A—C1A—C6A	120.9 (4)	C6A—C7—C8	112.3 (4)
C1A—C2A—C3A	127.9 (3)	C14—C7—C6B	117.2 (8)
C1A—C2A—Se1A	107.2 (3)	C8—C7—C6B	110.1 (7)
C3A—C2A—Se1A	124.6 (3)	C14—C7—H7	106.7
C2A—C3A—C4A	108.3 (3)	C6A—C7—H7	106.7
C2A—C3A—H3A1	110.0	C8—C7—H7	106.7
C4A—C3A—H3A1	110.0	C6B—C7—H7	104.9
C2A—C3A—H3A2	110.0	N4—N3—C15	117.2 (4)
C4A—C3A—H3A2	110.0	C9—C8—C13	117.4 (4)
H3A1—C3A—H3A2	108.4	C9—C8—C7	119.3 (4)
C3A—C4A—C5A	113.9 (5)	C13—C8—C7	123.3 (4)
C3A—C4A—H4A1	108.8	C15—C14—C7	125.3 (4)
C5A—C4A—H4A1	108.8	C15—C14—Se2	109.5 (3)
C3A—C4A—H4A2	108.8	C7—C14—Se2	124.9 (3)
C5A—C4A—H4A2	108.8	C14—C15—N3	115.6 (4)
H4A1—C4A—H4A2	107.7	C14—C15—C16	127.1 (4)
C6A—C5A—C4A	111.2 (5)	N3—C15—C16	117.4 (4)
C6A—C5A—H5A1	109.4	N3—N4—Se2	111.0 (3)
C4A—C5A—H5A1	109.4	C11—C12—C13	118.6 (5)
C6A—C5A—H5A2	109.4	C11—C12—H12	120.7
C4A—C5A—H5A2	109.4	C13—C12—H12	120.7
H5A1—C5A—H5A2	108.0	C21—C16—C17	117.7 (5)
C7—C6A—C1A	111.1 (8)	C21—C16—C15	120.7 (4)
C7—C6A—C5A	113.9 (7)	C17—C16—C15	121.6 (4)
C1A—C6A—C5A	105.8 (5)	C20—C19—C18	117.2 (5)
C7—C6A—H6A	108.7	C20—C19—C22	121.8 (6)
C1A—C6A—H6A	108.7	C18—C19—C22	121.0 (6)
C5A—C6A—H6A	108.7	C10—C9—C8	122.6 (5)
C2B—Se1B—N1B	88.3 (7)	C10—C9—H9	118.7
N2B—N1B—Se1B	110.4 (11)	C8—C9—H9	118.7
N1B—N2B—C1B	117.5 (14)	C10—C11—C12	121.7 (5)
C2B—C1B—N2B	117.3 (12)	C10—C11—Cl1	119.2 (4)
C2B—C1B—C6B	120.3 (12)	C12—C11—Cl1	119.0 (5)
N2B—C1B—C6B	122.3 (14)	C9—C10—C11	118.4 (5)
C1B—C2B—C3B	121.5 (15)	C9—C10—H10	120.8
C1B—C2B—Se1B	106.1 (9)	C11—C10—H10	120.8
C3B—C2B—Se1B	125.5 (11)	C12—C13—C8	121.2 (4)
C2B—C3B—C4B	106.9 (12)	C12—C13—H13	119.4
C2B—C3B—H3B1	110.3	C8—C13—H13	119.4
C4B—C3B—H3B1	110.3	C18—C17—C16	121.3 (5)
C2B—C3B—H3B2	110.3	C18—C17—H17	119.4
C4B—C3B—H3B2	110.3	C16—C17—H17	119.4
H3B1—C3B—H3B2	108.6	C17—C18—C19	121.0 (5)
C5B—C4B—C3B	106.3 (15)	C17—C18—H18	119.5
C5B—C4B—H4B1	110.5	C19—C18—H18	119.5
C3B—C4B—H4B1	110.5	C20—C21—C16	120.6 (5)
C5B—C4B—H4B2	110.5	C20—C21—H21	119.7
C3B—C4B—H4B2	110.5	C16—C21—H21	119.7
H4B1—C4B—H4B2	108.7	C21—C20—C19	122.2 (5)
C6B—C5B—C4B	112.9 (16)	C21—C20—H20	118.9
C6B—C5B—H5B1	109.0	C19—C20—H20	118.9
C4B—C5B—H5B1	109.0	C19—C22—H22A	109.5
C6B—C5B—H5B2	109.0	C19—C22—H22B	109.5
C4B—C5B—H5B2	109.0	H22A—C22—H22B	109.5
H5B1—C5B—H5B2	107.8	C19—C22—H22C	109.5
C1B—C6B—C5B	114.0 (14)	H22A—C22—H22C	109.5
C1B—C6B—C7	102 (3)	H22B—C22—H22C	109.5
C2A—Se1A—N1A—N2A	−2.8 (7)	C5B—C6B—C7—C6A	−177 (17)
Se1A—N1A—N2A—C1A	1.9 (13)	C1B—C6B—C7—C8	177.6 (12)
N1A—N2A—C1A—C2A	0.5 (17)	C5B—C6B—C7—C8	56.9 (16)
N1A—N2A—C1A—C6A	−179.9 (10)	C14—C7—C8—C9	109.2 (4)
N2A—C1A—C2A—C3A	−175.9 (10)	C6A—C7—C8—C9	−123.1 (5)
C6A—C1A—C2A—C3A	4.5 (16)	C6B—C7—C8—C9	−119.7 (11)
N2A—C1A—C2A—Se1A	−2.6 (14)	C14—C7—C8—C13	−71.1 (5)
C6A—C1A—C2A—Se1A	177.8 (9)	C6A—C7—C8—C13	56.7 (6)
N1A—Se1A—C2A—C1A	2.8 (7)	C6B—C7—C8—C13	60.0 (12)
N1A—Se1A—C2A—C3A	176.3 (7)	C6A—C7—C14—C15	127.4 (5)
C1A—C2A—C3A—C4A	−3.4 (12)	C8—C7—C14—C15	−105.5 (5)
Se1A—C2A—C3A—C4A	−175.6 (5)	C6B—C7—C14—C15	127.3 (10)
C2A—C3A—C4A—C5A	−29.7 (8)	C6A—C7—C14—Se2	−59.8 (5)
C3A—C4A—C5A—C6A	64.0 (7)	C8—C7—C14—Se2	67.3 (4)
C2A—C1A—C6A—C7	−97.8 (10)	C6B—C7—C14—Se2	−59.9 (10)
N2A—C1A—C6A—C7	82.7 (14)	N4—Se2—C14—C15	1.2 (3)
C2A—C1A—C6A—C5A	26.3 (14)	N4—Se2—C14—C7	−172.6 (4)
N2A—C1A—C6A—C5A	−153.3 (12)	C7—C14—C15—N3	172.5 (4)
C4A—C5A—C6A—C7	64.0 (7)	Se2—C14—C15—N3	−1.2 (5)
C4A—C5A—C6A—C1A	−58.3 (10)	C7—C14—C15—C16	−6.5 (7)
C2B—Se1B—N1B—N2B	5(3)	Se2—C14—C15—C16	179.8 (3)
Se1B—N1B—N2B—C1B	−2(5)	N4—N3—C15—C14	0.5 (6)
N1B—N2B—C1B—C2B	−3(7)	N4—N3—C15—C16	179.6 (4)
N1B—N2B—C1B—C6B	174 (4)	C15—N3—N4—Se2	0.5 (5)
N2B—C1B—C2B—C3B	158 (4)	C14—Se2—N4—N3	−1.0 (4)
C6B—C1B—C2B—C3B	−18 (6)	C14—C15—C16—C21	125.1 (5)
N2B—C1B—C2B—Se1B	6(5)	N3—C15—C16—C21	−53.8 (6)
C6B—C1B—C2B—Se1B	−170 (4)	C14—C15—C16—C17	−55.1 (7)
N1B—Se1B—C2B—C1B	−6(3)	N3—C15—C16—C17	126.0 (5)
N1B—Se1B—C2B—C3B	−157 (3)	C13—C8—C9—C10	−0.2 (7)
C1B—C2B—C3B—C4B	45 (4)	C7—C8—C9—C10	179.5 (4)
Se1B—C2B—C3B—C4B	−169 (2)	C13—C12—C11—C10	0.1 (8)
C2B—C3B—C4B—C5B	−64 (2)	C13—C12—C11—Cl1	179.0 (4)
C3B—C4B—C5B—C6B	63 (3)	C8—C9—C10—C11	0.5 (7)
C2B—C1B—C6B—C5B	12 (6)	C12—C11—C10—C9	−0.4 (8)
N2B—C1B—C6B—C5B	−164 (5)	Cl1—C11—C10—C9	−179.3 (4)
C2B—C1B—C6B—C7	−105 (4)	C11—C12—C13—C8	0.1 (7)
N2B—C1B—C6B—C7	79 (5)	C9—C8—C13—C12	−0.1 (7)
C4B—C5B—C6B—C1B	−36 (5)	C7—C8—C13—C12	−179.8 (4)
C4B—C5B—C6B—C7	77 (2)	C21—C16—C17—C18	−2.6 (7)
C1A—C6A—C7—C14	−65.9 (6)	C15—C16—C17—C18	177.6 (5)
C5A—C6A—C7—C14	174.8 (4)	C16—C17—C18—C19	0.8 (9)
C1A—C6A—C7—C8	167.9 (4)	C20—C19—C18—C17	1.1 (9)
C5A—C6A—C7—C8	48.6 (7)	C22—C19—C18—C17	−178.6 (6)
C1A—C6A—C7—C6B	112 (16)	C17—C16—C21—C20	2.6 (8)
C5A—C6A—C7—C6B	−7(16)	C15—C16—C21—C20	−177.6 (5)
C1B—C6B—C7—C14	−54.9 (18)	C16—C21—C20—C19	−0.8 (9)
C5B—C6B—C7—C14	−175.7 (10)	C18—C19—C20—C21	−1.1 (9)
C1B—C6B—C7—C6A	−57 (15)	C22—C19—C20—C21	178.6 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C6A—H6A···N2Ai	0.98	2.57	3.517 (16)	164
C10—H10···N4ii	0.93	2.61	3.467 (7)	153
C12—H12···N3iii	0.93	2.61	3.470 (7)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6A—H6A⋯N2Ai	0.98	2.57	3.517 (16)	164
C10—H10⋯N4ii	0.93	2.61	3.467 (7)	153
C12—H12⋯N3iii	0.93	2.61	3.470 (7)	153

Symmetry codes: (i) ; (ii) ; (iii) .