Chloridobis[2-(1,3-thia-zol-4-yl-κN)-1H-benzimidazole-κN(3)]cobalt(II) chloride dihydrate.

In the title compound, [CoCl(C(10)H(7)N(3)S)(2)]Cl·2H(2)O, the Co(II) atom is five-coordinated by four N atoms from two chelating 2-(1,3-thia-zol-4-yl)-1H-benzimidazole ligands and one Cl atom in a distorted trigonal-bipyramidal geometry. In the crystal, N-H⋯O and O-H⋯Cl hydrogen bonds and π-π inter-actions between the thia-zole, imidazole and benzene rings [centroid-to-centroid distances 3.546 (2), 3.683 (2) and 3.714 (2) Å] link the complex cations, chloride anions and uncoordinating water mol-ecules into a three-dimensional network.

Related literature

For related structures, see: Devereux et al. (2004 ▶, 2007 ▶); Flores-Alamo et al. (2010 ▶); Jean et al. (2002 ▶); Mothilal et al. (2004 ▶); Murugesan et al. (1998 ▶); Ren et al. (2010 ▶); Stanley et al. (2002 ▶); Trus & Marsh (1973 ▶); Wisniewski et al. (2001 ▶).

Experimental

Crystal data

[CoCl(C10H7N3S)2]Cl·2H2O

M = 568.35

Monoclinic,

a = 14.803 (4) Å

b = 11.709 (3) Å

c = 14.082 (4) Å

β = 101.439 (4)°

V = 2392.3 (11) Å3

Z = 4

Mo Kα radiation

μ = 1.15 mm−1

T = 296 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.803, T max = 0.803

12683 measured reflections

4200 independent reflections

3517 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.096

S = 1.05

4200 reflections

298 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.37 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812030371/hy2563sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030371/hy2563Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812030371/hy2563Isup3.cdx

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

[CoCl(C10H7N3S)2]Cl·2H2O	F(000) = 1156
Mr = 568.35	Dx = 1.578 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5625 reflections
a = 14.803 (4) Å	θ = 2.5–27.9°
b = 11.709 (3) Å	µ = 1.15 mm−1
c = 14.082 (4) Å	T = 296 K
β = 101.439 (4)°	Block, red
V = 2392.3 (11) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Bruker SMART 1000 CCD diffractometer	4200 independent reflections
Radiation source: fine-focus sealed tube	3517 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→17
Tmin = 0.803, Tmax = 0.803	k = −13→13
12683 measured reflections	l = −16→16

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0452P)2 + 1.5251P] where P = (Fo2 + 2Fc2)/3
4200 reflections	(Δ/σ)max < 0.001
298 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.37 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
Co1	0.24191 (2)	0.52351 (3)	0.80442 (2)	0.03535 (12)
N1	0.12865 (16)	0.48857 (19)	0.70875 (17)	0.0431 (5)
N2	0.19207 (15)	0.69958 (19)	0.75929 (16)	0.0439 (5)
N3	−0.00486 (16)	0.54257 (19)	0.62029 (16)	0.0445 (5)
H3	−0.0486	0.5863	0.5919	0.053*
N4	0.36009 (15)	0.57629 (19)	0.88293 (17)	0.0433 (5)
N5	0.32957 (16)	0.4841 (2)	0.70910 (17)	0.0463 (6)
N6	0.50953 (15)	0.60834 (19)	0.89573 (16)	0.0427 (5)
H6	0.5629	0.6109	0.8805	0.051*
O1	0.68432 (15)	0.6368 (2)	0.86990 (18)	0.0747 (7)
H1A	0.7236	0.6088	0.9164	0.090*
H1B	0.6967	0.6135	0.8168	0.090*
O2	0.15760 (14)	0.17298 (19)	0.95087 (16)	0.0608 (6)
H2A	0.1934	0.1473	0.9156	0.073*
H2B	0.1578	0.2455	0.9482	0.073*
S1	0.42099 (6)	0.43913 (9)	0.57955 (7)	0.0668 (3)
S2	0.14108 (6)	0.90259 (6)	0.71020 (6)	0.0563 (2)
Cl1	0.18070 (6)	0.45144 (7)	0.93089 (6)	0.0572 (2)
Cl2	0.29471 (6)	0.07173 (8)	0.83834 (7)	0.0652 (2)
C1	0.39292 (18)	0.6275 (2)	0.9725 (2)	0.0430 (6)
C2	0.3493 (2)	0.6578 (3)	1.0480 (2)	0.0565 (8)
H2	0.2865	0.6460	1.0436	0.068*
C3	0.4030 (2)	0.7058 (3)	1.1293 (2)	0.0637 (9)
H3A	0.3757	0.7268	1.1807	0.076*
C4	0.4968 (2)	0.7237 (3)	1.1363 (2)	0.0573 (8)
H4	0.5305	0.7565	1.1925	0.069*
C5	0.5412 (2)	0.6952 (2)	1.0641 (2)	0.0499 (7)
H5	0.6040	0.7076	1.0695	0.060*
C6	0.48778 (18)	0.6465 (2)	0.98172 (19)	0.0409 (6)
C7	0.43232 (18)	0.5669 (2)	0.84080 (19)	0.0407 (6)
C8	0.41976 (19)	0.5164 (2)	0.7457 (2)	0.0416 (6)
C9	0.4787 (2)	0.4974 (3)	0.6854 (2)	0.0520 (7)
H9	0.5414	0.5137	0.6996	0.062*
C10	0.3214 (2)	0.4410 (3)	0.6220 (2)	0.0599 (8)
H10	0.2658	0.4138	0.5865	0.072*
C11	0.08023 (19)	0.3911 (2)	0.6733 (2)	0.0436 (6)
C12	0.1039 (2)	0.2764 (3)	0.6844 (2)	0.0547 (7)
H12	0.1600	0.2529	0.7214	0.066*
C13	0.0396 (3)	0.1989 (3)	0.6377 (3)	0.0637 (9)
H13	0.0535	0.1214	0.6428	0.076*
C14	−0.0449 (3)	0.2327 (3)	0.5835 (2)	0.0628 (9)
H14	−0.0865	0.1772	0.5548	0.075*
C15	−0.0687 (2)	0.3454 (3)	0.5711 (2)	0.0545 (8)
H15	−0.1250	0.3680	0.5339	0.065*
C16	−0.00419 (19)	0.4249 (2)	0.61717 (19)	0.0425 (6)
C17	0.07502 (18)	0.5765 (2)	0.67555 (19)	0.0403 (6)
C18	0.10696 (18)	0.6918 (2)	0.69648 (19)	0.0423 (6)
C19	0.0698 (2)	0.7934 (2)	0.6639 (2)	0.0521 (7)
H19	0.0132	0.8024	0.6221	0.063*
C20	0.2169 (2)	0.8065 (2)	0.7725 (2)	0.0484 (7)
H20	0.2718	0.8284	0.8128	0.058*

	U11	U22	U33	U12	U13	U23
Co1	0.02582 (19)	0.0390 (2)	0.0398 (2)	−0.00224 (13)	0.00312 (14)	−0.00274 (14)
N1	0.0372 (12)	0.0425 (13)	0.0489 (13)	−0.0005 (10)	0.0068 (10)	0.0016 (10)
N2	0.0379 (12)	0.0443 (13)	0.0486 (13)	0.0001 (10)	0.0065 (10)	−0.0020 (10)
N3	0.0375 (12)	0.0488 (14)	0.0441 (13)	0.0003 (10)	0.0007 (10)	0.0059 (10)
N4	0.0344 (12)	0.0449 (13)	0.0497 (13)	−0.0011 (10)	0.0064 (10)	−0.0044 (10)
N5	0.0364 (12)	0.0513 (14)	0.0491 (14)	−0.0013 (10)	0.0033 (10)	−0.0072 (11)
N6	0.0341 (12)	0.0482 (13)	0.0450 (13)	−0.0057 (10)	0.0055 (10)	0.0002 (10)
O1	0.0463 (13)	0.1013 (19)	0.0761 (16)	−0.0047 (13)	0.0114 (11)	0.0041 (14)
O2	0.0544 (13)	0.0559 (13)	0.0701 (14)	−0.0024 (10)	0.0072 (11)	−0.0076 (11)
S1	0.0620 (5)	0.0828 (6)	0.0582 (5)	−0.0049 (4)	0.0180 (4)	−0.0234 (4)
S2	0.0639 (5)	0.0412 (4)	0.0634 (5)	0.0021 (3)	0.0121 (4)	0.0026 (3)
Cl1	0.0574 (5)	0.0584 (5)	0.0558 (4)	−0.0100 (4)	0.0112 (4)	0.0053 (3)
Cl2	0.0516 (5)	0.0696 (5)	0.0732 (5)	−0.0039 (4)	0.0096 (4)	−0.0142 (4)
C1	0.0428 (15)	0.0374 (14)	0.0481 (15)	−0.0033 (12)	0.0074 (12)	−0.0040 (12)
C2	0.0489 (17)	0.0591 (19)	0.064 (2)	−0.0050 (14)	0.0161 (15)	−0.0134 (15)
C3	0.072 (2)	0.062 (2)	0.060 (2)	−0.0073 (17)	0.0206 (17)	−0.0183 (16)
C4	0.067 (2)	0.0513 (18)	0.0500 (17)	−0.0102 (15)	0.0022 (15)	−0.0114 (14)
C5	0.0502 (17)	0.0418 (16)	0.0540 (17)	−0.0086 (13)	0.0017 (14)	−0.0009 (13)
C6	0.0422 (15)	0.0365 (14)	0.0422 (15)	−0.0023 (11)	0.0040 (12)	0.0009 (11)
C7	0.0383 (14)	0.0383 (14)	0.0441 (15)	−0.0007 (11)	0.0049 (12)	0.0017 (11)
C8	0.0377 (14)	0.0399 (14)	0.0465 (15)	−0.0012 (11)	0.0068 (12)	0.0021 (12)
C9	0.0439 (16)	0.0540 (17)	0.0602 (19)	−0.0032 (13)	0.0155 (14)	−0.0054 (14)
C10	0.0512 (18)	0.070 (2)	0.0560 (19)	−0.0053 (16)	0.0051 (15)	−0.0192 (16)
C11	0.0408 (15)	0.0463 (16)	0.0448 (15)	−0.0032 (12)	0.0111 (12)	0.0000 (12)
C12	0.0535 (18)	0.0493 (17)	0.0613 (19)	0.0034 (14)	0.0110 (15)	0.0033 (14)
C13	0.077 (2)	0.0449 (18)	0.072 (2)	−0.0066 (16)	0.0224 (19)	−0.0007 (15)
C14	0.077 (2)	0.055 (2)	0.0586 (19)	−0.0255 (17)	0.0189 (18)	−0.0063 (15)
C15	0.0516 (18)	0.067 (2)	0.0447 (16)	−0.0163 (15)	0.0076 (13)	−0.0009 (14)
C16	0.0414 (15)	0.0493 (16)	0.0370 (14)	−0.0069 (12)	0.0080 (12)	0.0004 (12)
C17	0.0375 (14)	0.0443 (15)	0.0394 (14)	−0.0005 (12)	0.0081 (11)	0.0021 (11)
C18	0.0411 (15)	0.0460 (16)	0.0390 (14)	0.0004 (12)	0.0064 (12)	0.0006 (12)
C19	0.0536 (17)	0.0484 (17)	0.0523 (17)	0.0048 (14)	0.0051 (14)	0.0033 (13)
C20	0.0451 (16)	0.0449 (17)	0.0551 (17)	−0.0025 (13)	0.0100 (13)	−0.0057 (13)

Co1—N1	1.974 (2)	C1—C6	1.402 (4)
Co1—N4	1.974 (2)	C2—C3	1.377 (4)
Co1—N5	2.095 (2)	C2—H2	0.9300
Co1—N2	2.239 (2)	C3—C4	1.390 (5)
Co1—Cl1	2.3120 (9)	C3—H3A	0.9300
N1—C17	1.327 (4)	C4—C5	1.357 (4)
N1—C11	1.387 (4)	C4—H4	0.9300
N2—C20	1.308 (4)	C5—C6	1.391 (4)
N2—C18	1.391 (3)	C5—H5	0.9300
N3—C17	1.340 (3)	C7—C8	1.442 (4)
N3—C16	1.379 (4)	C8—C9	1.351 (4)
N3—H3	0.8600	C9—H9	0.9300
N4—C7	1.326 (3)	C10—H10	0.9300
N4—C1	1.393 (3)	C11—C12	1.389 (4)
N5—C10	1.310 (4)	C11—C16	1.397 (4)
N5—C8	1.385 (4)	C12—C13	1.383 (4)
N6—C7	1.338 (3)	C12—H12	0.9300
N6—C6	1.387 (3)	C13—C14	1.388 (5)
N6—H6	0.8600	C13—H13	0.9300
O1—H1A	0.8500	C14—C15	1.368 (5)
O1—H1B	0.8500	C14—H14	0.9300
O2—H2A	0.8500	C15—C16	1.398 (4)
O2—H2B	0.8500	C15—H15	0.9300
S1—C10	1.698 (3)	C17—C18	1.442 (4)
S1—C9	1.707 (3)	C18—C19	1.352 (4)
S2—C19	1.702 (3)	C19—H19	0.9300
S2—C20	1.704 (3)	C20—H20	0.9300
C1—C2	1.395 (4)
N1—Co1—N4	170.18 (10)	C6—C5—H5	121.7
N1—Co1—N5	93.86 (9)	N6—C6—C5	132.0 (3)
N4—Co1—N5	80.51 (9)	N6—C6—C1	105.6 (2)
N1—Co1—N2	79.03 (9)	C5—C6—C1	122.4 (3)
N4—Co1—N2	94.37 (9)	N4—C7—N6	112.5 (2)
N5—Co1—N2	103.42 (9)	N4—C7—C8	118.9 (2)
N1—Co1—Cl1	92.32 (7)	N6—C7—C8	128.6 (2)
N4—Co1—Cl1	97.01 (7)	C9—C8—N5	114.6 (3)
N5—Co1—Cl1	143.16 (7)	C9—C8—C7	132.1 (3)
N2—Co1—Cl1	113.41 (6)	N5—C8—C7	113.2 (2)
C17—N1—C11	106.3 (2)	C8—C9—S1	109.9 (2)
C17—N1—Co1	116.58 (19)	C8—C9—H9	125.0
C11—N1—Co1	136.43 (19)	S1—C9—H9	125.0
C20—N2—C18	110.3 (2)	N5—C10—S1	114.1 (2)
C20—N2—Co1	140.7 (2)	N5—C10—H10	122.9
C18—N2—Co1	109.04 (17)	S1—C10—H10	122.9
C17—N3—C16	107.7 (2)	N1—C11—C12	130.9 (3)
C17—N3—H3	126.2	N1—C11—C16	108.1 (2)
C16—N3—H3	126.2	C12—C11—C16	121.0 (3)
C7—N4—C1	105.8 (2)	C13—C12—C11	116.5 (3)
C7—N4—Co1	115.27 (18)	C13—C12—H12	121.7
C1—N4—Co1	138.82 (18)	C11—C12—H12	121.7
C10—N5—C8	110.9 (2)	C12—C13—C14	122.3 (3)
C10—N5—Co1	136.9 (2)	C12—C13—H13	118.8
C8—N5—Co1	112.05 (18)	C14—C13—H13	118.8
C7—N6—C6	107.6 (2)	C15—C14—C13	121.8 (3)
C7—N6—H6	126.2	C15—C14—H14	119.1
C6—N6—H6	126.2	C13—C14—H14	119.1
H1A—O1—H1B	108.7	C14—C15—C16	116.6 (3)
H2A—O2—H2B	108.7	C14—C15—H15	121.7
C10—S1—C9	90.38 (15)	C16—C15—H15	121.7
C19—S2—C20	89.78 (15)	N3—C16—C11	106.0 (2)
N4—C1—C2	131.9 (3)	N3—C16—C15	132.2 (3)
N4—C1—C6	108.4 (2)	C11—C16—C15	121.8 (3)
C2—C1—C6	119.7 (3)	N1—C17—N3	111.9 (2)
C3—C2—C1	117.4 (3)	N1—C17—C18	120.4 (2)
C3—C2—H2	121.3	N3—C17—C18	127.7 (2)
C1—C2—H2	121.3	C19—C18—N2	114.5 (3)
C2—C3—C4	121.6 (3)	C19—C18—C17	131.3 (3)
C2—C3—H3A	119.2	N2—C18—C17	114.2 (2)
C4—C3—H3A	119.2	C18—C19—S2	110.6 (2)
C5—C4—C3	122.4 (3)	C18—C19—H19	124.7
C5—C4—H4	118.8	S2—C19—H19	124.7
C3—C4—H4	118.8	N2—C20—S2	114.9 (2)
C4—C5—C6	116.5 (3)	N2—C20—H20	122.5
C4—C5—H5	121.7	S2—C20—H20	122.5
N5—Co1—N1—C17	−110.9 (2)	C10—N5—C8—C9	0.1 (4)
N2—Co1—N1—C17	−7.97 (19)	Co1—N5—C8—C9	−177.3 (2)
Cl1—Co1—N1—C17	105.44 (19)	C10—N5—C8—C7	178.7 (3)
N5—Co1—N1—C11	80.0 (3)	Co1—N5—C8—C7	1.3 (3)
N2—Co1—N1—C11	−177.0 (3)	N4—C7—C8—C9	178.9 (3)
Cl1—Co1—N1—C11	−63.6 (3)	N6—C7—C8—C9	−0.7 (5)
N1—Co1—N2—C20	−174.8 (3)	N4—C7—C8—N5	0.6 (4)
N4—Co1—N2—C20	−2.2 (3)	N6—C7—C8—N5	−179.0 (3)
N5—Co1—N2—C20	−83.5 (3)	N5—C8—C9—S1	0.6 (3)
Cl1—Co1—N2—C20	97.4 (3)	C7—C8—C9—S1	−177.6 (3)
N1—Co1—N2—C18	4.89 (17)	C10—S1—C9—C8	−0.9 (3)
N4—Co1—N2—C18	177.54 (17)	C8—N5—C10—S1	−0.9 (4)
N5—Co1—N2—C18	96.27 (18)	Co1—N5—C10—S1	175.71 (17)
Cl1—Co1—N2—C18	−82.88 (17)	C9—S1—C10—N5	1.0 (3)
N5—Co1—N4—C7	2.24 (19)	C17—N1—C11—C12	179.2 (3)
N2—Co1—N4—C7	−100.7 (2)	Co1—N1—C11—C12	−11.0 (5)
Cl1—Co1—N4—C7	145.09 (19)	C17—N1—C11—C16	0.4 (3)
N5—Co1—N4—C1	178.8 (3)	Co1—N1—C11—C16	170.2 (2)
N2—Co1—N4—C1	75.9 (3)	N1—C11—C12—C13	−179.0 (3)
Cl1—Co1—N4—C1	−38.4 (3)	C16—C11—C12—C13	−0.3 (4)
N1—Co1—N5—C10	−6.5 (3)	C11—C12—C13—C14	−0.9 (5)
N4—Co1—N5—C10	−178.4 (3)	C12—C13—C14—C15	1.7 (5)
N2—Co1—N5—C10	−86.2 (3)	C13—C14—C15—C16	−1.1 (5)
Cl1—Co1—N5—C10	92.5 (3)	C17—N3—C16—C11	−0.1 (3)
N1—Co1—N5—C8	170.01 (19)	C17—N3—C16—C15	179.9 (3)
N4—Co1—N5—C8	−1.89 (18)	N1—C11—C16—N3	−0.2 (3)
N2—Co1—N5—C8	90.38 (19)	C12—C11—C16—N3	−179.1 (3)
Cl1—Co1—N5—C8	−90.9 (2)	N1—C11—C16—C15	179.8 (2)
C7—N4—C1—C2	−179.5 (3)	C12—C11—C16—C15	0.9 (4)
Co1—N4—C1—C2	3.8 (5)	C14—C15—C16—N3	179.8 (3)
C7—N4—C1—C6	−0.7 (3)	C14—C15—C16—C11	−0.2 (4)
Co1—N4—C1—C6	−177.4 (2)	C11—N1—C17—N3	−0.4 (3)
N4—C1—C2—C3	178.7 (3)	Co1—N1—C17—N3	−172.59 (17)
C6—C1—C2—C3	0.0 (4)	C11—N1—C17—C18	−177.6 (2)
C1—C2—C3—C4	0.1 (5)	Co1—N1—C17—C18	10.2 (3)
C2—C3—C4—C5	0.0 (5)	C16—N3—C17—N1	0.3 (3)
C3—C4—C5—C6	−0.1 (5)	C16—N3—C17—C18	177.3 (3)
C7—N6—C6—C5	179.0 (3)	C20—N2—C18—C19	0.0 (3)
C7—N6—C6—C1	−1.5 (3)	Co1—N2—C18—C19	−179.8 (2)
C4—C5—C6—N6	179.6 (3)	C20—N2—C18—C17	178.4 (2)
C4—C5—C6—C1	0.2 (4)	Co1—N2—C18—C17	−1.4 (3)
N4—C1—C6—N6	1.4 (3)	N1—C17—C18—C19	172.7 (3)
C2—C1—C6—N6	−179.7 (3)	N3—C17—C18—C19	−4.0 (5)
N4—C1—C6—C5	−179.1 (2)	N1—C17—C18—N2	−5.4 (4)
C2—C1—C6—C5	−0.1 (4)	N3—C17—C18—N2	177.9 (2)
C1—N4—C7—N6	−0.3 (3)	N2—C18—C19—S2	0.6 (3)
Co1—N4—C7—N6	177.35 (18)	C17—C18—C19—S2	−177.5 (2)
C1—N4—C7—C8	−179.9 (2)	C20—S2—C19—C18	−0.7 (2)
Co1—N4—C7—C8	−2.3 (3)	C18—N2—C20—S2	−0.6 (3)
C6—N6—C7—N4	1.2 (3)	Co1—N2—C20—S2	179.15 (17)
C6—N6—C7—C8	−179.2 (3)	C19—S2—C20—N2	0.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O2i	0.86	1.90	2.748 (3)	169
N6—H6···O1	0.86	1.86	2.704 (3)	168
O1—H1B···Cl2ii	0.85	2.27	3.104 (3)	169
O1—H1A···Cl1iii	0.85	2.43	3.272 (3)	169
O2—H2B···Cl1	0.85	2.45	3.296 (3)	171
O2—H2A···Cl2	0.85	2.21	3.052 (2)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O2i	0.86	1.90	2.748 (3)	169
N6—H6⋯O1	0.86	1.86	2.704 (3)	168
O1—H1B⋯Cl2ii	0.85	2.27	3.104 (3)	169
O1—H1A⋯Cl1iii	0.85	2.43	3.272 (3)	169
O2—H2B⋯Cl1	0.85	2.45	3.296 (3)	171
O2—H2A⋯Cl2	0.85	2.21	3.052 (2)	174

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