N-(6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)benzene-sulfonamide.

The asymmetric unit of the title compound, C13H11ClN4O2S, contains two mol-ecules (A and B), in which the dihedral angles between the 1H-imidazo[4,5-c]pyridine system and terminal phenyl ring are 80.83 (10) and 62.34 (1)°. In the crystal, A-B dimers are linked by pairs of N-H⋯N hydrogen bonds, which generate R (2) 2(10) loops. The dimers are linked by C-H⋯O and C-H⋯Cl inter-actions, generating a three-dimensional network. Aromatic π-π stacking inter-actions [shortest centroid-centroid distance = 3.5211 (12) Å] are also observed.

Related literature

For biological background, see: Kulkarni & Newman (2007 ▶). For a related structure, see: Kandri Rodi et al. (2013 ▶).

Experimental

Crystal data

C13H11ClN4O2S

M = 322.77

Monoclinic,

a = 13.1045 (4) Å

b = 14.7259 (5) Å

c = 14.6953 (6) Å

β = 95.127 (3)°

V = 2824.49 (17) Å3

Z = 8

Mo Kα radiation

μ = 0.43 mm−1

T = 293 K

0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.770, T max = 1.000

16038 measured reflections

4972 independent reflections

3759 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.098

S = 1.04

4972 reflections

379 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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, 2012 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814005388/hb7208sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814005388/hb7208Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814005388/hb7208Isup3.cml

CCDC reference: 990803

Additional supporting information: crystallographic information; 3D view; checkCIF report

C13H11ClN4O2S	F(000) = 1328
Mr = 322.77	Dx = 1.518 Mg m−3
Monoclinic, P21/c	Melting point: 376 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.1045 (4) Å	Cell parameters from 4972 reflections
b = 14.7259 (5) Å	θ = 2.8–25.0°
c = 14.6953 (6) Å	µ = 0.43 mm−1
β = 95.127 (3)°	T = 293 K
V = 2824.49 (17) Å3	Plate, colourless
Z = 8	0.24 × 0.20 × 0.12 mm

Bruker SMART CCD diffractometer	4972 independent reflections
Radiation source: fine-focus sealed tube	3759 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω and φ scans	θmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −15→15
Tmin = 0.770, Tmax = 1.000	k = −17→17
16038 measured reflections	l = −17→17

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0619P)2] where P = (Fo2 + 2Fc2)/3
4972 reflections	(Δ/σ)max = 0.001
379 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

Experimental. IR cm-1 (KBr) 3435, 1388; Anal. Calcd for C13H11ClN4O2S C, 45.82; H, 2.96; N, 16.44%; Found, C, 45.18; H, 2.92; N, 15.84%.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cl1A	0.20678 (5)	0.52370 (5)	0.40718 (5)	0.06025 (19)
Cl1B	0.93941 (5)	0.41848 (4)	0.38570 (5)	0.05977 (19)
S2A	0.28936 (4)	0.22270 (3)	0.58582 (4)	0.03821 (16)
S2B	0.70463 (4)	0.13503 (3)	0.40663 (4)	0.03622 (15)
O3A	0.26710 (11)	0.21724 (10)	0.48964 (11)	0.0500 (4)
O3B	0.70151 (13)	0.19837 (10)	0.47946 (11)	0.0522 (4)
O4A	0.32556 (11)	0.14347 (9)	0.63449 (13)	0.0562 (5)
O4B	0.63810 (11)	0.05785 (9)	0.40271 (11)	0.0461 (4)
N5A	0.51992 (13)	0.58429 (10)	0.64248 (12)	0.0357 (4)
N5B	0.62508 (13)	0.45541 (11)	0.14780 (12)	0.0369 (4)
N6A	0.30372 (12)	0.41345 (11)	0.52175 (12)	0.0371 (4)
N6B	0.79517 (13)	0.30202 (11)	0.33564 (12)	0.0376 (4)
N7A	0.37871 (13)	0.29776 (10)	0.61344 (13)	0.0439 (5)
H7A	0.4314	0.2801	0.6480	0.053*
N7B	0.67403 (13)	0.18711 (11)	0.30975 (12)	0.0394 (4)
H7B	0.6335	0.1599	0.2693	0.047*
N8A	0.52770 (13)	0.43954 (10)	0.69189 (12)	0.0360 (4)
N8B	0.56595 (12)	0.31475 (11)	0.16965 (12)	0.0364 (4)
C9A	0.17905 (15)	0.26081 (13)	0.63400 (15)	0.0354 (5)
C9B	0.83185 (15)	0.09728 (13)	0.40267 (14)	0.0354 (5)
C10A	0.1679 (2)	0.23876 (17)	0.72382 (18)	0.0609 (7)
H10A	0.2202	0.2094	0.7593	0.073*
C10B	0.91108 (18)	0.14379 (15)	0.44983 (16)	0.0482 (6)
H10B	0.8982	0.1949	0.4842	0.058*
C11A	0.0783 (3)	0.2610 (2)	0.7596 (2)	0.0800 (9)
H11A	0.0695	0.2463	0.8200	0.096*
C11B	1.01033 (19)	0.11297 (18)	0.44508 (19)	0.0594 (7)
H11B	1.0645	0.1433	0.4771	0.071*
C12A	0.0013 (2)	0.30470 (19)	0.7073 (2)	0.0755 (9)
H12A	−0.0596	0.3187	0.7321	0.091*
C12B	1.0294 (2)	0.03867 (19)	0.39389 (19)	0.0615 (7)
H12B	1.0964	0.0189	0.3909	0.074*
C13A	0.01382 (19)	0.32755 (18)	0.6197 (2)	0.0641 (7)
H13A	−0.0383	0.3579	0.5849	0.077*
C13B	0.9501 (2)	−0.00710 (18)	0.34674 (18)	0.0577 (7)
H13B	0.9635	−0.0576	0.3117	0.069*
C14A	0.10334 (16)	0.30612 (15)	0.58193 (17)	0.0458 (6)
H14A	0.1122	0.3222	0.5219	0.055*
C14B	0.85071 (18)	0.02174 (14)	0.35123 (16)	0.0458 (6)
H14B	0.7968	−0.0094	0.3198	0.055*
C15A	0.37606 (14)	0.38857 (12)	0.58513 (14)	0.0318 (4)
C15B	0.71004 (15)	0.27352 (12)	0.28880 (13)	0.0321 (5)
C16A	0.30231 (16)	0.50038 (14)	0.49461 (15)	0.0378 (5)
C16B	0.82753 (15)	0.38663 (14)	0.32074 (14)	0.0376 (5)
C17A	0.36691 (15)	0.56812 (13)	0.52574 (14)	0.0356 (5)
H17A	0.3617	0.6274	0.5041	0.043*
C17B	0.78186 (16)	0.44845 (13)	0.26077 (14)	0.0367 (5)
H17B	0.8070	0.5069	0.2538	0.044*
C18A	0.44159 (15)	0.54000 (12)	0.59313 (13)	0.0298 (4)
C18B	0.69432 (14)	0.41563 (13)	0.21132 (13)	0.0317 (4)
C19A	0.44741 (14)	0.45033 (12)	0.62405 (13)	0.0290 (4)
C19B	0.65665 (14)	0.32852 (12)	0.22385 (13)	0.0309 (4)
C20A	0.56688 (17)	0.52153 (13)	0.69992 (15)	0.0386 (5)
H20A	0.6223	0.5356	0.7415	0.046*
C20B	0.55180 (16)	0.39220 (14)	0.12623 (15)	0.0401 (5)
H20B	0.4959	0.4029	0.0840	0.048*
C21A	0.54967 (18)	0.67998 (13)	0.63396 (16)	0.0468 (6)
H21A	0.5035	0.7092	0.5887	0.070*
H21B	0.6182	0.6833	0.6159	0.070*
H21C	0.5467	0.7099	0.6917	0.070*
C21B	0.62941 (19)	0.54775 (14)	0.11289 (18)	0.0530 (6)
H21D	0.6901	0.5772	0.1399	0.080*
H21E	0.5700	0.5808	0.1280	0.080*
H21F	0.6310	0.5461	0.0477	0.080*

	U11	U22	U33	U12	U13	U23
Cl1A	0.0494 (4)	0.0661 (4)	0.0616 (4)	0.0194 (3)	−0.0152 (3)	0.0047 (3)
Cl1B	0.0511 (4)	0.0597 (4)	0.0645 (4)	−0.0155 (3)	−0.0170 (3)	0.0071 (3)
S2A	0.0297 (3)	0.0228 (3)	0.0614 (4)	−0.0001 (2)	−0.0003 (2)	−0.0053 (2)
S2B	0.0421 (3)	0.0276 (3)	0.0390 (3)	−0.0011 (2)	0.0037 (2)	0.0059 (2)
O3A	0.0468 (9)	0.0467 (9)	0.0569 (11)	−0.0055 (7)	0.0075 (8)	−0.0219 (7)
O3B	0.0701 (11)	0.0442 (9)	0.0439 (10)	−0.0004 (8)	0.0137 (8)	−0.0035 (7)
O4A	0.0366 (8)	0.0248 (7)	0.1057 (14)	0.0018 (6)	−0.0022 (9)	0.0105 (8)
O4B	0.0462 (9)	0.0344 (8)	0.0572 (10)	−0.0067 (7)	0.0017 (8)	0.0130 (7)
N5A	0.0416 (10)	0.0235 (8)	0.0423 (11)	−0.0050 (7)	0.0055 (8)	−0.0038 (7)
N5B	0.0379 (10)	0.0332 (9)	0.0396 (10)	0.0005 (8)	0.0031 (8)	0.0124 (8)
N6A	0.0325 (9)	0.0314 (9)	0.0467 (11)	0.0043 (7)	−0.0009 (8)	−0.0028 (8)
N6B	0.0372 (10)	0.0336 (9)	0.0413 (11)	−0.0010 (8)	−0.0012 (8)	0.0063 (7)
N7A	0.0336 (9)	0.0254 (9)	0.0695 (14)	−0.0021 (7)	−0.0125 (9)	0.0058 (8)
N7B	0.0438 (10)	0.0285 (9)	0.0437 (11)	−0.0036 (8)	−0.0083 (8)	0.0071 (7)
N8A	0.0404 (10)	0.0297 (9)	0.0372 (10)	−0.0031 (7)	0.0001 (8)	−0.0019 (7)
N8B	0.0340 (9)	0.0362 (9)	0.0387 (10)	−0.0022 (8)	0.0012 (8)	0.0083 (8)
C9A	0.0366 (11)	0.0258 (10)	0.0434 (13)	−0.0020 (9)	0.0016 (10)	−0.0051 (9)
C9B	0.0400 (11)	0.0297 (10)	0.0356 (12)	−0.0018 (9)	−0.0016 (9)	0.0104 (9)
C10A	0.0735 (18)	0.0581 (15)	0.0509 (17)	0.0107 (14)	0.0045 (14)	0.0047 (12)
C10B	0.0552 (15)	0.0413 (12)	0.0451 (14)	−0.0063 (11)	−0.0117 (11)	0.0010 (10)
C11A	0.112 (3)	0.075 (2)	0.059 (2)	0.0138 (19)	0.0413 (19)	0.0038 (15)
C11B	0.0455 (14)	0.0673 (17)	0.0621 (18)	−0.0127 (13)	−0.0139 (12)	0.0145 (14)
C12A	0.070 (2)	0.0649 (18)	0.098 (3)	0.0096 (15)	0.0439 (19)	−0.0142 (17)
C12B	0.0413 (14)	0.0714 (18)	0.072 (2)	0.0066 (13)	0.0078 (13)	0.0200 (15)
C13A	0.0477 (15)	0.0657 (17)	0.080 (2)	0.0208 (13)	0.0115 (14)	−0.0072 (15)
C13B	0.0556 (16)	0.0572 (15)	0.0608 (17)	0.0078 (13)	0.0083 (13)	−0.0008 (13)
C14A	0.0399 (12)	0.0465 (13)	0.0508 (15)	0.0105 (10)	0.0024 (11)	−0.0005 (11)
C14B	0.0480 (14)	0.0406 (12)	0.0478 (14)	−0.0033 (10)	−0.0011 (11)	−0.0016 (10)
C15A	0.0319 (10)	0.0243 (9)	0.0393 (12)	0.0022 (8)	0.0044 (9)	−0.0036 (8)
C15B	0.0335 (11)	0.0271 (10)	0.0362 (12)	0.0017 (9)	0.0061 (9)	0.0040 (8)
C16A	0.0350 (11)	0.0386 (12)	0.0394 (13)	0.0117 (10)	0.0013 (10)	−0.0018 (9)
C16B	0.0346 (11)	0.0399 (12)	0.0381 (13)	−0.0043 (9)	0.0028 (9)	0.0002 (9)
C17A	0.0401 (11)	0.0287 (10)	0.0394 (12)	0.0078 (9)	0.0106 (10)	0.0025 (9)
C17B	0.0390 (11)	0.0317 (10)	0.0400 (13)	−0.0066 (9)	0.0065 (10)	0.0053 (9)
C18A	0.0345 (11)	0.0264 (10)	0.0301 (11)	0.0021 (8)	0.0117 (9)	−0.0037 (8)
C18B	0.0344 (10)	0.0299 (10)	0.0318 (11)	0.0005 (9)	0.0092 (9)	0.0065 (8)
C19A	0.0310 (10)	0.0269 (10)	0.0297 (11)	0.0007 (8)	0.0063 (9)	−0.0019 (8)
C19B	0.0306 (10)	0.0298 (10)	0.0330 (12)	0.0012 (8)	0.0066 (9)	0.0024 (8)
C20A	0.0412 (12)	0.0351 (11)	0.0379 (13)	−0.0038 (9)	−0.0044 (10)	−0.0052 (9)
C20B	0.0350 (11)	0.0429 (12)	0.0412 (13)	−0.0033 (10)	−0.0034 (10)	0.0116 (10)
C21A	0.0570 (14)	0.0276 (11)	0.0568 (15)	−0.0101 (10)	0.0108 (12)	−0.0030 (10)
C21B	0.0605 (15)	0.0373 (12)	0.0606 (16)	−0.0016 (11)	0.0013 (13)	0.0230 (11)

Cl1A—C16A	1.746 (2)	C10B—C11B	1.385 (3)
Cl1B—C16B	1.741 (2)	C10B—H10B	0.9300
S2A—O3A	1.4198 (17)	C11A—C12A	1.373 (4)
S2A—O4A	1.4273 (15)	C11A—H11A	0.9300
S2A—N7A	1.6347 (17)	C11B—C12B	1.363 (4)
S2A—C9A	1.757 (2)	C11B—H11B	0.9300
S2B—O3B	1.4230 (16)	C12A—C13A	1.354 (4)
S2B—O4B	1.4305 (14)	C12A—H12A	0.9300
S2B—N7B	1.6352 (17)	C12B—C13B	1.373 (4)
S2B—C9B	1.763 (2)	C12B—H12B	0.9300
N5A—C20A	1.361 (3)	C13A—C14A	1.379 (3)
N5A—C18A	1.368 (2)	C13A—H13A	0.9300
N5A—C21A	1.470 (2)	C13B—C14B	1.377 (3)
N5B—C20B	1.354 (3)	C13B—H13B	0.9300
N5B—C18B	1.374 (2)	C14A—H14A	0.9300
N5B—C21B	1.456 (2)	C14B—H14B	0.9300
N6A—C15A	1.320 (2)	C15A—C19A	1.390 (3)
N6A—C16A	1.341 (3)	C15B—C19B	1.392 (3)
N6B—C15B	1.326 (3)	C16A—C17A	1.361 (3)
N6B—C16B	1.340 (2)	C16B—C17B	1.367 (3)
N7A—C15A	1.400 (2)	C17A—C18A	1.392 (3)
N7A—H7A	0.8600	C17A—H17A	0.9300
N7B—C15B	1.401 (2)	C17B—C18B	1.389 (3)
N7B—H7B	0.8600	C17B—H17B	0.9300
N8A—C20A	1.313 (2)	C18A—C19A	1.396 (3)
N8A—C19A	1.392 (3)	C18B—C19B	1.393 (3)
N8B—C20B	1.312 (2)	C20A—H20A	0.9300
N8B—C19B	1.385 (2)	C20B—H20B	0.9300
C9A—C14A	1.371 (3)	C21A—H21A	0.9600
C9A—C10A	1.380 (3)	C21A—H21B	0.9600
C9B—C10B	1.378 (3)	C21A—H21C	0.9600
C9B—C14B	1.380 (3)	C21B—H21D	0.9600
C10A—C11A	1.369 (4)	C21B—H21E	0.9600
C10A—H10A	0.9300	C21B—H21F	0.9600
O3A—S2A—O4A	118.82 (10)	C12B—C13B—H13B	120.0
O3A—S2A—N7A	111.37 (10)	C14B—C13B—H13B	120.0
O4A—S2A—N7A	103.28 (9)	C9A—C14A—C13A	119.1 (2)
O3A—S2A—C9A	108.41 (10)	C9A—C14A—H14A	120.5
O4A—S2A—C9A	107.92 (10)	C13A—C14A—H14A	120.5
N7A—S2A—C9A	106.31 (9)	C9B—C14B—C13B	119.4 (2)
O3B—S2B—O4B	119.51 (9)	C9B—C14B—H14B	120.3
O3B—S2B—N7B	109.03 (9)	C13B—C14B—H14B	120.3
O4B—S2B—N7B	103.68 (9)	N6A—C15A—C19A	121.52 (17)
O3B—S2B—C9B	108.80 (10)	N6A—C15A—N7A	118.16 (17)
O4B—S2B—C9B	108.84 (9)	C19A—C15A—N7A	120.32 (18)
N7B—S2B—C9B	106.16 (9)	N6B—C15B—C19B	121.33 (17)
C20A—N5A—C18A	106.34 (15)	N6B—C15B—N7B	117.25 (17)
C20A—N5A—C21A	126.50 (18)	C19B—C15B—N7B	121.38 (18)
C18A—N5A—C21A	127.14 (18)	N6A—C16A—C17A	127.47 (19)
C20B—N5B—C18B	106.11 (15)	N6A—C16A—Cl1A	113.37 (16)
C20B—N5B—C21B	127.47 (19)	C17A—C16A—Cl1A	119.14 (16)
C18B—N5B—C21B	126.40 (18)	N6B—C16B—C17B	126.69 (19)
C15A—N6A—C16A	117.71 (17)	N6B—C16B—Cl1B	115.09 (16)
C15B—N6B—C16B	118.25 (18)	C17B—C16B—Cl1B	118.22 (15)
C15A—N7A—S2A	125.03 (15)	C16A—C17A—C18A	113.45 (18)
C15A—N7A—H7A	117.5	C16A—C17A—H17A	123.3
S2A—N7A—H7A	117.5	C18A—C17A—H17A	123.3
C15B—N7B—S2B	123.79 (15)	C16B—C17B—C18B	113.53 (18)
C15B—N7B—H7B	118.1	C16B—C17B—H17B	123.2
S2B—N7B—H7B	118.1	C18B—C17B—H17B	123.2
C20A—N8A—C19A	102.94 (16)	N5A—C18A—C17A	133.00 (17)
C20B—N8B—C19B	103.25 (16)	N5A—C18A—C19A	105.18 (17)
C14A—C9A—C10A	121.0 (2)	C17A—C18A—C19A	121.82 (18)
C14A—C9A—S2A	120.72 (17)	N5B—C18B—C17B	132.22 (17)
C10A—C9A—S2A	118.14 (18)	N5B—C18B—C19B	105.20 (17)
C10B—C9B—C14B	120.8 (2)	C17B—C18B—C19B	122.51 (18)
C10B—C9B—S2B	119.93 (17)	N8A—C19A—C15A	131.09 (17)
C14B—C9B—S2B	119.24 (16)	N8A—C19A—C18A	110.89 (17)
C11A—C10A—C9A	118.7 (3)	C15A—C19A—C18A	118.02 (18)
C11A—C10A—H10A	120.7	N8B—C19B—C18B	110.79 (17)
C9A—C10A—H10A	120.7	N8B—C19B—C15B	131.45 (17)
C9B—C10B—C11B	118.7 (2)	C18B—C19B—C15B	117.66 (18)
C9B—C10B—H10B	120.6	N8A—C20A—N5A	114.65 (19)
C11B—C10B—H10B	120.6	N8A—C20A—H20A	122.7
C10A—C11A—C12A	120.6 (3)	N5A—C20A—H20A	122.7
C10A—C11A—H11A	119.7	N8B—C20B—N5B	114.65 (18)
C12A—C11A—H11A	119.7	N8B—C20B—H20B	122.7
C12B—C11B—C10B	120.6 (2)	N5B—C20B—H20B	122.7
C12B—C11B—H11B	119.7	N5A—C21A—H21A	109.5
C10B—C11B—H11B	119.7	N5A—C21A—H21B	109.5
C13A—C12A—C11A	120.2 (2)	H21A—C21A—H21B	109.5
C13A—C12A—H12A	119.9	N5A—C21A—H21C	109.5
C11A—C12A—H12A	119.9	H21A—C21A—H21C	109.5
C11B—C12B—C13B	120.3 (2)	H21B—C21A—H21C	109.5
C11B—C12B—H12B	119.8	N5B—C21B—H21D	109.5
C13B—C12B—H12B	119.8	N5B—C21B—H21E	109.5
C12A—C13A—C14A	120.4 (3)	H21D—C21B—H21E	109.5
C12A—C13A—H13A	119.8	N5B—C21B—H21F	109.5
C14A—C13A—H13A	119.8	H21D—C21B—H21F	109.5
C12B—C13B—C14B	120.0 (2)	H21E—C21B—H21F	109.5
O3A—S2A—N7A—C15A	54.0 (2)	C15B—N6B—C16B—C17B	−0.4 (3)
O4A—S2A—N7A—C15A	−177.38 (17)	C15B—N6B—C16B—Cl1B	179.63 (15)
C9A—S2A—N7A—C15A	−63.9 (2)	N6A—C16A—C17A—C18A	0.2 (3)
O3B—S2B—N7B—C15B	42.58 (18)	Cl1A—C16A—C17A—C18A	−177.92 (14)
O4B—S2B—N7B—C15B	170.92 (16)	N6B—C16B—C17B—C18B	−1.1 (3)
C9B—S2B—N7B—C15B	−74.47 (18)	Cl1B—C16B—C17B—C18B	178.91 (15)
O3A—S2A—C9A—C14A	−20.6 (2)	C20A—N5A—C18A—C17A	179.0 (2)
O4A—S2A—C9A—C14A	−150.49 (17)	C21A—N5A—C18A—C17A	−2.4 (3)
N7A—S2A—C9A—C14A	99.25 (18)	C20A—N5A—C18A—C19A	−0.8 (2)
O3A—S2A—C9A—C10A	155.31 (17)	C21A—N5A—C18A—C19A	177.74 (17)
O4A—S2A—C9A—C10A	25.4 (2)	C16A—C17A—C18A—N5A	−179.73 (19)
N7A—S2A—C9A—C10A	−84.85 (19)	C16A—C17A—C18A—C19A	0.1 (3)
O3B—S2B—C9B—C10B	−14.6 (2)	C20B—N5B—C18B—C17B	−176.7 (2)
O4B—S2B—C9B—C10B	−146.40 (17)	C21B—N5B—C18B—C17B	2.1 (3)
N7B—S2B—C9B—C10B	102.56 (18)	C20B—N5B—C18B—C19B	0.0 (2)
O3B—S2B—C9B—C14B	166.09 (16)	C21B—N5B—C18B—C19B	178.77 (19)
O4B—S2B—C9B—C14B	34.3 (2)	C16B—C17B—C18B—N5B	177.4 (2)
N7B—S2B—C9B—C14B	−76.70 (18)	C16B—C17B—C18B—C19B	1.2 (3)
C14A—C9A—C10A—C11A	1.7 (4)	C20A—N8A—C19A—C15A	−179.5 (2)
S2A—C9A—C10A—C11A	−174.2 (2)	C20A—N8A—C19A—C18A	0.2 (2)
C14B—C9B—C10B—C11B	−0.4 (3)	N6A—C15A—C19A—N8A	178.71 (19)
S2B—C9B—C10B—C11B	−179.61 (18)	N7A—C15A—C19A—N8A	−0.5 (3)
C9A—C10A—C11A—C12A	−0.3 (4)	N6A—C15A—C19A—C18A	−1.0 (3)
C9B—C10B—C11B—C12B	0.7 (4)	N7A—C15A—C19A—C18A	179.78 (17)
C10A—C11A—C12A—C13A	−0.9 (5)	N5A—C18A—C19A—N8A	0.4 (2)
C10B—C11B—C12B—C13B	−0.5 (4)	C17A—C18A—C19A—N8A	−179.47 (17)
C11A—C12A—C13A—C14A	0.8 (4)	N5A—C18A—C19A—C15A	−179.87 (16)
C11B—C12B—C13B—C14B	−0.2 (4)	C17A—C18A—C19A—C15A	0.3 (3)
C10A—C9A—C14A—C13A	−1.7 (3)	C20B—N8B—C19B—C18B	0.4 (2)
S2A—C9A—C14A—C13A	174.03 (18)	C20B—N8B—C19B—C15B	176.6 (2)
C12A—C13A—C14A—C9A	0.5 (4)	N5B—C18B—C19B—N8B	−0.3 (2)
C10B—C9B—C14B—C13B	−0.3 (3)	C17B—C18B—C19B—N8B	176.86 (18)
S2B—C9B—C14B—C13B	178.94 (18)	N5B—C18B—C19B—C15B	−177.09 (17)
C12B—C13B—C14B—C9B	0.6 (4)	C17B—C18B—C19B—C15B	0.0 (3)
C16A—N6A—C15A—C19A	1.2 (3)	N6B—C15B—C19B—N8B	−177.66 (19)
C16A—N6A—C15A—N7A	−179.50 (18)	N7B—C15B—C19B—N8B	0.0 (3)
S2A—N7A—C15A—N6A	−9.7 (3)	N6B—C15B—C19B—C18B	−1.6 (3)
S2A—N7A—C15A—C19A	169.53 (15)	N7B—C15B—C19B—C18B	176.01 (17)
C16B—N6B—C15B—C19B	1.8 (3)	C19A—N8A—C20A—N5A	−0.8 (2)
C16B—N6B—C15B—N7B	−175.93 (17)	C18A—N5A—C20A—N8A	1.1 (2)
S2B—N7B—C15B—N6B	21.4 (2)	C21A—N5A—C20A—N8A	−177.51 (18)
S2B—N7B—C15B—C19B	−156.28 (15)	C19B—N8B—C20B—N5B	−0.4 (2)
C15A—N6A—C16A—C17A	−0.9 (3)	C18B—N5B—C20B—N8B	0.2 (2)
C15A—N6A—C16A—Cl1A	177.34 (15)	C21B—N5B—C20B—N8B	−178.51 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N7A—H7A···N8Bi	0.86	2.25	3.014 (2)	148
N7B—H7B···N8Aii	0.86	2.25	3.092 (2)	165
C13A—H13A···Cl1Aiii	0.93	2.82	3.620 (3)	144
C20A—H20A···O4Aiv	0.93	2.47	3.243 (3)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7A—H7A⋯N8B i	0.86	2.25	3.014 (2)	148
N7B—H7B⋯N8A ii	0.86	2.25	3.092 (2)	165
C13A—H13A⋯Cl1A iii	0.93	2.82	3.620 (3)	144
C20A—H20A⋯O4A iv	0.93	2.47	3.243 (3)	141

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