5-Chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothia-diazol-4-amine (tizanidine).

There are two independent mol-ecules (A and B) with similar conformations in the asymmetric unit of the title compound, C(9)H(8)ClN(5)S. The benzothia-diazole ring systems of both mol-ecules are essentially planar [maximum deviation = 0.021 (2) Å in mol-ecule A and 0.022 (1) Å in mol-ecule B] and make dihedral angles of 68.78 (9) and 54.39 (8)°, respectively, with the mean planes of their 4,5-dihydro-1H-imidazole rings. An intra-molecular N-H⋯Cl hydrogen bond occurs in mol-ecule B. In the crystal, both mol-ecules form centrosymmetric dimers through π-stacking of their benzothia-diazole rings, with inter-planar distances of 3.3174 (7) and 3.2943 (6) Å. These dimers are further linked via pairs of N-H⋯N hydrogen bonds with the dihydro-imidazole rings as the hydrogen-bonding donors and one of the benzothia-diazole N atoms as the acceptors, generating R(2) (2)(16) ring motifs. The A(2) and B(2) dimers in turn form additional N-H⋯N hydrogen bonds with the secondary amine as the H-atom donor and the dihydro-imidazole N atom as the acceptor. These R(2) (2)(8)-type inter-actions connect the A(2) and B(2) dimers with each other, forming infinite chains along [1[Formula: see text]1].

Related literature

For the medicinal importance of tizanidine, see: Koch et al. (1989 ▶); Shellenberger et al. (1999 ▶); Tse et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C9H8ClN5S

M = 253.72

Triclinic,

a = 7.6927 (3) Å

b = 10.8558 (4) Å

c = 12.9969 (5) Å

α = 95.790 (1)°

β = 101.126 (1)°

γ = 92.192 (1)°

V = 1057.69 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.54 mm−1

T = 296 K

0.29 × 0.18 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

17897 measured reflections

5104 independent reflections

4449 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.120

S = 1.03

5104 reflections

302 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.65 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008348/zl2351sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008348/zl2351Isup2.hkl

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

C9H8ClN5S	Z = 4
Mr = 253.72	F(000) = 520
Triclinic, P1	Dx = 1.593 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6927 (3) Å	Cell parameters from 9959 reflections
b = 10.8558 (4) Å	θ = 2.9–28.3°
c = 12.9969 (5) Å	µ = 0.54 mm−1
α = 95.790 (1)°	T = 296 K
β = 101.126 (1)°	Block, orange
γ = 92.192 (1)°	0.29 × 0.18 × 0.08 mm
V = 1057.69 (7) Å3

Bruker APEXII CCD diffractometer	4449 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.024
graphite	θmax = 28.3°, θmin = 3.2°
φ and ω scans	h = −10→10
17897 measured reflections	k = −14→14
5104 independent 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0635P)2 + 0.4931P] where P = (Fo2 + 2Fc2)/3
5104 reflections	(Δ/σ)max = 0.001
302 parameters	Δρmax = 0.65 e Å−3
5 restraints	Δρmin = −0.43 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.40681 (8)	0.26166 (5)	0.72358 (5)	0.0597 (2)
S1A	0.85136 (8)	0.69598 (5)	0.58255 (5)	0.0609 (2)
N1A	0.6430 (3)	0.71482 (15)	0.57232 (14)	0.0518 (5)
N2A	0.8692 (2)	0.56543 (15)	0.63157 (15)	0.0504 (5)
N3A	0.7911 (2)	0.33724 (14)	0.71346 (12)	0.0441 (5)
N4A	0.6996 (2)	0.18129 (15)	0.56630 (12)	0.0426 (4)
N5A	0.9113 (2)	0.14570 (13)	0.69909 (11)	0.0393 (4)
C1A	0.4819 (3)	0.39656 (17)	0.68103 (13)	0.0410 (5)
C2A	0.3519 (3)	0.48262 (19)	0.65002 (14)	0.0449 (6)
C3A	0.3954 (3)	0.58968 (17)	0.61257 (15)	0.0452 (5)
C4A	0.5753 (3)	0.61502 (15)	0.60785 (13)	0.0407 (5)
C5A	0.7058 (2)	0.52907 (15)	0.64166 (13)	0.0378 (5)
C6A	0.6584 (2)	0.41428 (15)	0.67789 (13)	0.0375 (5)
C7A	0.7965 (2)	0.22922 (15)	0.66323 (12)	0.0333 (4)
C8A	0.7270 (3)	0.0496 (2)	0.55046 (19)	0.0588 (7)
C9A	0.9066 (3)	0.0408 (2)	0.62174 (16)	0.0526 (6)
Cl1B	1.12566 (6)	0.18138 (5)	1.13956 (4)	0.0505 (1)
S1B	1.35483 (8)	−0.13008 (5)	0.75206 (4)	0.0509 (2)
N1B	1.3845 (2)	−0.19353 (14)	0.86079 (14)	0.0469 (5)
N2B	1.2747 (2)	−0.00089 (13)	0.78769 (11)	0.0380 (4)
N3B	1.13963 (18)	0.19625 (12)	0.90223 (11)	0.0321 (3)
N4B	1.32552 (18)	0.36020 (13)	1.01366 (12)	0.0352 (4)
N5B	1.09790 (19)	0.40512 (13)	0.89434 (12)	0.0388 (4)
C1B	1.2069 (2)	0.07385 (17)	1.05470 (13)	0.0359 (5)
C2B	1.2668 (2)	−0.03721 (19)	1.09644 (15)	0.0452 (6)
C3B	1.3290 (2)	−0.12898 (18)	1.03814 (16)	0.0454 (5)
C4B	1.3311 (2)	−0.11275 (15)	0.93194 (14)	0.0367 (4)
C5B	1.26880 (19)	−0.00179 (14)	0.88987 (12)	0.0306 (4)
C6B	1.20705 (18)	0.09766 (14)	0.95246 (12)	0.0288 (4)
C7B	1.18549 (19)	0.31124 (14)	0.93720 (12)	0.0297 (4)
C8B	1.3016 (2)	0.49159 (16)	1.03987 (15)	0.0406 (5)
C9B	1.1930 (2)	0.52377 (16)	0.93606 (16)	0.0424 (5)
H8AA	0.73030	0.02310	0.47730	0.0710*
H8BA	0.63520	0.00040	0.57190	0.0710*
H2A	0.23490	0.46520	0.65550	0.0540*
H9AA	0.91290	−0.03620	0.65370	0.0630*
H3A	0.30950	0.64460	0.59070	0.0540*
H9BA	1.00250	0.04780	0.58350	0.0630*
HN3A	0.887 (3)	0.368 (3)	0.7644 (17)	0.0720*
HN4A	0.597 (3)	0.209 (3)	0.544 (2)	0.0720*
H2B	1.26270	−0.04660	1.16630	0.0540*
H3B	1.36890	−0.20030	1.06680	0.0550*
H8AB	1.41440	0.53940	1.05880	0.0490*
H8BB	1.23730	0.50460	1.09690	0.0490*
H9AB	1.11220	0.58780	0.94760	0.0510*
H9BB	1.26870	0.55020	0.88970	0.0510*
HN3B	1.072 (3)	0.179 (2)	0.8391 (15)	0.0610*
HN4B	1.370 (3)	0.317 (2)	1.0608 (18)	0.0610*

	U11	U22	U33	U12	U13	U23
Cl1A	0.0697 (3)	0.0577 (3)	0.0579 (3)	0.0072 (2)	0.0179 (3)	0.0245 (2)
S1A	0.0653 (3)	0.0384 (3)	0.0738 (4)	−0.0043 (2)	0.0007 (3)	0.0089 (2)
N1A	0.0690 (11)	0.0306 (7)	0.0500 (9)	0.0073 (7)	−0.0036 (8)	0.0047 (7)
N2A	0.0487 (9)	0.0364 (8)	0.0591 (10)	0.0036 (6)	−0.0049 (7)	0.0019 (7)
N3A	0.0512 (9)	0.0320 (7)	0.0401 (8)	0.0131 (6)	−0.0144 (6)	0.0016 (6)
N4A	0.0459 (8)	0.0443 (8)	0.0320 (7)	0.0146 (6)	−0.0074 (6)	0.0016 (6)
N5A	0.0450 (8)	0.0329 (7)	0.0348 (7)	0.0129 (6)	−0.0057 (6)	0.0016 (6)
C1A	0.0548 (10)	0.0375 (9)	0.0300 (8)	0.0107 (7)	0.0041 (7)	0.0054 (6)
C2A	0.0492 (10)	0.0483 (10)	0.0367 (9)	0.0146 (8)	0.0070 (7)	0.0002 (7)
C3A	0.0545 (10)	0.0386 (9)	0.0392 (9)	0.0227 (8)	−0.0003 (8)	−0.0008 (7)
C4A	0.0570 (10)	0.0274 (7)	0.0320 (8)	0.0130 (7)	−0.0048 (7)	−0.0017 (6)
C5A	0.0466 (9)	0.0286 (7)	0.0324 (8)	0.0089 (6)	−0.0053 (6)	−0.0021 (6)
C6A	0.0496 (9)	0.0305 (8)	0.0275 (7)	0.0119 (7)	−0.0054 (6)	0.0008 (6)
C7A	0.0368 (7)	0.0328 (7)	0.0286 (7)	0.0056 (6)	−0.0007 (6)	0.0082 (6)
C8A	0.0549 (12)	0.0512 (11)	0.0555 (12)	0.0199 (9)	−0.0183 (9)	−0.0148 (9)
C9A	0.0517 (11)	0.0503 (11)	0.0456 (10)	0.0224 (9)	−0.0109 (8)	−0.0116 (8)
Cl1B	0.0461 (2)	0.0679 (3)	0.0390 (2)	−0.0006 (2)	0.0148 (2)	0.0023 (2)
S1B	0.0633 (3)	0.0406 (3)	0.0434 (3)	0.0166 (2)	−0.0008 (2)	−0.0036 (2)
N1B	0.0479 (9)	0.0308 (7)	0.0561 (10)	0.0076 (6)	−0.0055 (7)	0.0050 (7)
N2B	0.0453 (8)	0.0328 (7)	0.0325 (7)	0.0074 (6)	−0.0015 (6)	0.0034 (5)
N3B	0.0340 (6)	0.0299 (6)	0.0288 (6)	0.0031 (5)	−0.0030 (5)	0.0034 (5)
N4B	0.0299 (6)	0.0325 (7)	0.0393 (7)	0.0007 (5)	−0.0014 (5)	0.0014 (5)
N5B	0.0375 (7)	0.0281 (6)	0.0467 (8)	0.0076 (5)	−0.0014 (6)	0.0007 (6)
C1B	0.0292 (7)	0.0442 (9)	0.0332 (8)	−0.0048 (6)	0.0033 (6)	0.0074 (7)
C2B	0.0396 (9)	0.0578 (11)	0.0386 (9)	−0.0080 (8)	0.0012 (7)	0.0236 (8)
C3B	0.0422 (9)	0.0414 (9)	0.0514 (10)	−0.0022 (7)	−0.0029 (8)	0.0246 (8)
C4B	0.0309 (7)	0.0293 (7)	0.0456 (9)	−0.0014 (6)	−0.0057 (6)	0.0100 (6)
C5B	0.0280 (7)	0.0273 (7)	0.0330 (7)	−0.0019 (5)	−0.0034 (5)	0.0065 (6)
C6B	0.0243 (6)	0.0293 (7)	0.0304 (7)	−0.0020 (5)	−0.0012 (5)	0.0056 (5)
C7B	0.0265 (6)	0.0311 (7)	0.0312 (7)	0.0037 (5)	0.0052 (5)	0.0016 (6)
C8B	0.0336 (8)	0.0370 (8)	0.0477 (10)	−0.0001 (6)	0.0066 (7)	−0.0087 (7)
C9B	0.0403 (9)	0.0292 (8)	0.0560 (11)	0.0053 (6)	0.0071 (7)	0.0007 (7)

Cl1A—C1A	1.734 (2)	C1A—C2A	1.424 (3)
Cl1B—C1B	1.7412 (18)	C1A—C6A	1.373 (3)
S1A—N2A	1.6114 (18)	C2A—C3A	1.359 (3)
S1A—N1A	1.605 (2)	C3A—C4A	1.415 (3)
S1B—N2B	1.6145 (16)	C4A—C5A	1.434 (3)
S1B—N1B	1.6148 (18)	C5A—C6A	1.434 (2)
N1A—C4A	1.345 (3)	C8A—C9A	1.520 (3)
N2A—C5A	1.338 (2)	C2A—H2A	0.9300
N3A—C7A	1.290 (2)	C3A—H3A	0.9300
N3A—C6A	1.384 (2)	C8A—H8AA	0.9700
N4A—C7A	1.375 (2)	C8A—H8BA	0.9700
N4A—C8A	1.453 (3)	C9A—H9BA	0.9700
N5A—C7A	1.344 (2)	C9A—H9AA	0.9700
N5A—C9A	1.436 (3)	C1B—C6B	1.379 (2)
N3A—HN3A	0.92 (2)	C1B—C2B	1.428 (3)
N4A—HN4A	0.86 (3)	C2B—C3B	1.349 (3)
N1B—C4B	1.343 (2)	C3B—C4B	1.412 (3)
N2B—C5B	1.339 (2)	C4B—C5B	1.434 (2)
N3B—C7B	1.296 (2)	C5B—C6B	1.437 (2)
N3B—C6B	1.376 (2)	C8B—C9B	1.524 (3)
N4B—C8B	1.460 (2)	C2B—H2B	0.9300
N4B—C7B	1.366 (2)	C3B—H3B	0.9300
N5B—C9B	1.457 (2)	C8B—H8AB	0.9700
N5B—C7B	1.351 (2)	C8B—H8BB	0.9700
N3B—HN3B	0.88 (2)	C9B—H9AB	0.9700
N4B—HN4B	0.84 (2)	C9B—H9BB	0.9700
N1A—S1A—N2A	101.46 (9)	N4A—C8A—H8BA	111.00
N1B—S1B—N2B	101.08 (8)	C9A—C8A—H8AA	111.00
S1A—N1A—C4A	105.99 (15)	C9A—C8A—H8BA	111.00
S1A—N2A—C5A	106.15 (13)	N4A—C8A—H8AA	111.00
C6A—N3A—C7A	120.01 (15)	H8AA—C8A—H8BA	109.00
C7A—N4A—C8A	108.65 (16)	H9AA—C9A—H9BA	109.00
C7A—N5A—C9A	111.44 (15)	C8A—C9A—H9BA	111.00
C6A—N3A—HN3A	120.0 (19)	C8A—C9A—H9AA	111.00
C7A—N3A—HN3A	118.9 (18)	N5A—C9A—H9AA	111.00
C8A—N4A—HN4A	121 (2)	N5A—C9A—H9BA	111.00
C7A—N4A—HN4A	119.2 (19)	Cl1B—C1B—C6B	119.74 (13)
S1B—N1B—C4B	106.09 (12)	C2B—C1B—C6B	123.76 (16)
S1B—N2B—C5B	106.29 (11)	Cl1B—C1B—C2B	116.49 (13)
C6B—N3B—C7B	123.72 (14)	C1B—C2B—C3B	122.33 (17)
C7B—N4B—C8B	108.92 (13)	C2B—C3B—C4B	117.52 (17)
C7B—N5B—C9B	110.47 (14)	C3B—C4B—C5B	120.03 (15)
C6B—N3B—HN3B	117.1 (14)	N1B—C4B—C3B	126.69 (16)
C7B—N3B—HN3B	118.8 (14)	N1B—C4B—C5B	113.27 (15)
C7B—N4B—HN4B	119.4 (15)	N2B—C5B—C6B	124.10 (14)
C8B—N4B—HN4B	120.4 (15)	C4B—C5B—C6B	122.63 (14)
C2A—C1A—C6A	124.01 (18)	N2B—C5B—C4B	113.27 (14)
Cl1A—C1A—C6A	119.56 (15)	N3B—C6B—C1B	128.30 (15)
Cl1A—C1A—C2A	116.43 (17)	N3B—C6B—C5B	117.62 (14)
C1A—C2A—C3A	121.3 (2)	C1B—C6B—C5B	113.69 (14)
C2A—C3A—C4A	117.99 (19)	N3B—C7B—N4B	129.45 (15)
N1A—C4A—C3A	126.55 (19)	N4B—C7B—N5B	108.75 (14)
N1A—C4A—C5A	113.2 (2)	N3B—C7B—N5B	121.71 (14)
C3A—C4A—C5A	120.22 (16)	N4B—C8B—C9B	101.13 (14)
C4A—C5A—C6A	121.60 (15)	N5B—C9B—C8B	101.10 (14)
N2A—C5A—C6A	125.17 (15)	C1B—C2B—H2B	119.00
N2A—C5A—C4A	113.17 (16)	C3B—C2B—H2B	119.00
N3A—C6A—C1A	125.98 (16)	C2B—C3B—H3B	121.00
N3A—C6A—C5A	118.99 (14)	C4B—C3B—H3B	121.00
C1A—C6A—C5A	114.83 (15)	N4B—C8B—H8AB	112.00
N3A—C7A—N5A	122.83 (15)	N4B—C8B—H8BB	112.00
N3A—C7A—N4A	128.44 (16)	C9B—C8B—H8AB	112.00
N4A—C7A—N5A	108.66 (14)	C9B—C8B—H8BB	112.00
N4A—C8A—C9A	102.08 (17)	H8AB—C8B—H8BB	109.00
N5A—C9A—C8A	101.67 (17)	N5B—C9B—H9AB	112.00
C1A—C2A—H2A	119.00	N5B—C9B—H9BB	112.00
C3A—C2A—H2A	119.00	C8B—C9B—H9AB	112.00
C2A—C3A—H3A	121.00	C8B—C9B—H9BB	112.00
C4A—C3A—H3A	121.00	H9AB—C9B—H9BB	109.00
N2A—S1A—N1A—C4A	−0.35 (15)	C2A—C1A—C6A—C5A	0.8 (2)
N1A—S1A—N2A—C5A	0.49 (16)	Cl1A—C1A—C2A—C3A	−178.11 (15)
N2B—S1B—N1B—C4B	−0.13 (13)	C6A—C1A—C2A—C3A	1.2 (3)
N1B—S1B—N2B—C5B	0.42 (13)	Cl1A—C1A—C6A—C5A	−179.89 (12)
S1A—N1A—C4A—C5A	0.10 (18)	C1A—C2A—C3A—C4A	−1.7 (3)
S1A—N1A—C4A—C3A	−179.03 (15)	C2A—C3A—C4A—C5A	0.2 (3)
S1A—N2A—C5A—C6A	176.96 (14)	C2A—C3A—C4A—N1A	179.23 (18)
S1A—N2A—C5A—C4A	−0.48 (19)	C3A—C4A—C5A—N2A	179.45 (17)
C6A—N3A—C7A—N4A	10.0 (3)	C3A—C4A—C5A—C6A	1.9 (3)
C7A—N3A—C6A—C5A	−115.36 (18)	N1A—C4A—C5A—N2A	0.3 (2)
C7A—N3A—C6A—C1A	70.1 (2)	N1A—C4A—C5A—C6A	−177.28 (16)
C6A—N3A—C7A—N5A	−173.51 (15)	C4A—C5A—C6A—N3A	−177.48 (15)
C8A—N4A—C7A—N3A	−169.83 (18)	N2A—C5A—C6A—C1A	−179.54 (17)
C7A—N4A—C8A—C9A	−24.8 (2)	C4A—C5A—C6A—C1A	−2.3 (2)
C8A—N4A—C7A—N5A	13.3 (2)	N2A—C5A—C6A—N3A	5.3 (3)
C7A—N5A—C9A—C8A	−20.2 (2)	N4A—C8A—C9A—N5A	26.1 (2)
C9A—N5A—C7A—N3A	−171.84 (17)	Cl1B—C1B—C6B—N3B	−4.3 (2)
C9A—N5A—C7A—N4A	5.3 (2)	C2B—C1B—C6B—C5B	1.7 (2)
S1B—N1B—C4B—C5B	−0.18 (17)	C6B—C1B—C2B—C3B	−0.1 (3)
S1B—N1B—C4B—C3B	178.69 (15)	Cl1B—C1B—C6B—C5B	−176.84 (11)
S1B—N2B—C5B—C6B	179.30 (13)	C2B—C1B—C6B—N3B	174.28 (16)
S1B—N2B—C5B—C4B	−0.57 (17)	Cl1B—C1B—C2B—C3B	178.50 (14)
C7B—N3B—C6B—C1B	55.9 (2)	C1B—C2B—C3B—C4B	−0.9 (3)
C7B—N3B—C6B—C5B	−131.72 (16)	C2B—C3B—C4B—N1B	−178.73 (17)
C6B—N3B—C7B—N5B	−170.11 (15)	C2B—C3B—C4B—C5B	0.1 (2)
C6B—N3B—C7B—N4B	13.9 (3)	N1B—C4B—C5B—N2B	0.5 (2)
C8B—N4B—C7B—N5B	14.92 (18)	N1B—C4B—C5B—C6B	−179.36 (14)
C7B—N4B—C8B—C9B	−28.11 (16)	C3B—C4B—C5B—N2B	−178.44 (15)
C8B—N4B—C7B—N3B	−168.70 (16)	C3B—C4B—C5B—C6B	1.7 (2)
C7B—N5B—C9B—C8B	−22.90 (17)	C4B—C5B—C6B—C1B	−2.5 (2)
C9B—N5B—C7B—N3B	−170.68 (15)	N2B—C5B—C6B—C1B	177.67 (15)
C9B—N5B—C7B—N4B	6.04 (19)	C4B—C5B—C6B—N3B	−175.91 (14)
Cl1A—C1A—C6A—N3A	−5.1 (2)	N2B—C5B—C6B—N3B	4.2 (2)
C2A—C1A—C6A—N3A	175.59 (17)	N4B—C8B—C9B—N5B	29.36 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N3A—HN3A···N5B	0.92 (2)	2.10 (2)	3.003 (2)	168 (3)
N4A—HN4A···N1Ai	0.86 (3)	2.38 (3)	3.205 (3)	160 (2)
N3B—HN3B···N5A	0.88 (2)	1.98 (2)	2.864 (2)	177 (2)
N4B—HN4B···Cl1B	0.84 (2)	2.75 (2)	3.1927 (15)	114 (2)
N4B—HN4B···N1Bii	0.84 (2)	2.48 (2)	3.227 (2)	150 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3A—HN3A⋯N5B	0.92 (2)	2.10 (2)	3.003 (2)	168 (3)
N4A—HN4A⋯N1Ai	0.86 (3)	2.38 (3)	3.205 (3)	160 (2)
N3B—HN3B⋯N5A	0.88 (2)	1.98 (2)	2.864 (2)	177 (2)
N4B—HN4B⋯Cl1B	0.84 (2)	2.75 (2)	3.1927 (15)	114 (2)
N4B—HN4B⋯N1Bii	0.84 (2)	2.48 (2)	3.227 (2)	150 (2)

Symmetry codes: (i) ; (ii) .