(E)-4-(2-Chloro-benzyl-ideneamino)-3-(2-chloro-phen-yl)-1H-1,2,4-triazole-5(4H)-thione-(E)-1,5-bis-(2-chloro-benzyl-idene)thio-carbonohydrazide-methanol (1/1/1).

In the title compound, C(15)H(12)Cl(2)N(4)S·C(15)H(10)Cl(2)N(4)S·C(2)H(6)O, the two chloro-phenyl rings of the triazole derivative form dihedral angles of 65.7 (2) and 44.2 (2)° with the triazole ring. In the thio-carbonohydrazide derivative, the dihedral angle between the two chloro-phenyl rings is 5.4 (2)°. In the crystal, the triazole, thio-carbonohydrazide and methanol mol-ecules are linked by N-H⋯O, N-H⋯S and O-H⋯S hydrogen bonds, forming a hexa-meric unit.

Related literature

For general background to Schiff bases, see: Ren et al. (1999 ▶); Yang et al. (2005 ▶); Sen et al. (1998 ▶); Xia et al. (2007 ▶). For the biological activity of Schiff bases, see: Liang (2003 ▶); Bacci et al. (2005 ▶).

Experimental

Crystal data

C15H10Cl2N4S·C15H12Cl2N4S·C2H6O

M = 746.54

Triclinic,

a = 7.7086 (6) Å

b = 10.9999 (9) Å

c = 20.9827 (16) Å

α = 94.678 (1)°

β = 92.083 (1)°

γ = 99.851 (1)°

V = 1744.8 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.50 mm−1

T = 293 K

0.35 × 0.26 × 0.23 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.845, T max = 0.894

9324 measured reflections

6154 independent reflections

3724 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.111

S = 1.01

6154 reflections

425 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809053203/ci2984sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053203/ci2984Isup2.hkl

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

C15H10Cl2N4S·C15H12Cl2N4S·C2H6O	Z = 2
Mr = 746.54	F(000) = 768
Triclinic, P1	Dx = 1.421 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7086 (6) Å	Cell parameters from 1667 reflections
b = 10.9999 (9) Å	θ = 2.2–20.5°
c = 20.9827 (16) Å	µ = 0.50 mm−1
α = 94.678 (1)°	T = 293 K
β = 92.083 (1)°	Block, colourless
γ = 99.851 (1)°	0.35 × 0.26 × 0.23 mm
V = 1744.8 (2) Å3

Bruker SMART APEX diffractometer	6154 independent reflections
Radiation source: fine-focus sealed tube	3724 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 25.1°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→9
Tmin = 0.845, Tmax = 0.894	k = −12→13
9324 measured reflections	l = −24→24

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0365P)2 + 0.4564P] where P = (Fo2 + 2Fc2)/3
6154 reflections	(Δ/σ)max = 0.001
425 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.25 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
S1	0.25610 (13)	1.26698 (8)	0.43362 (4)	0.0574 (3)
S2	0.40630 (12)	0.14705 (9)	0.24096 (4)	0.0614 (3)
Cl1	0.15231 (15)	0.94451 (10)	0.71997 (4)	0.0836 (3)
Cl2	0.48468 (13)	0.77336 (9)	0.21104 (4)	0.0738 (3)
Cl3	0.21316 (12)	0.52305 (8)	0.10925 (5)	0.0689 (3)
Cl4	0.22413 (15)	−0.15631 (9)	0.07317 (5)	0.0861 (3)
O1	0.1682 (4)	0.7954 (3)	0.52080 (14)	0.0837 (8)
H1	0.0608	0.7901	0.5211	0.126*
N1	0.1820 (3)	1.1229 (2)	0.54344 (12)	0.0487 (7)
N2	0.2441 (3)	1.0597 (2)	0.49247 (11)	0.0472 (7)
H2	0.2608	0.9847	0.4944	0.057*
N3	0.3341 (3)	1.0539 (2)	0.39024 (11)	0.0506 (7)
H3	0.3534	1.0877	0.3550	0.061*
N4	0.3618 (3)	0.9349 (2)	0.39441 (11)	0.0468 (6)
N5	0.0553 (4)	0.3611 (2)	0.26242 (12)	0.0529 (7)
N6	0.1796 (3)	0.2949 (2)	0.28209 (11)	0.0542 (7)
H6	0.2121	0.2943	0.3217	0.065*
N7	0.1565 (3)	0.2589 (2)	0.18135 (11)	0.0459 (6)
N8	0.1743 (3)	0.2251 (2)	0.11665 (11)	0.0463 (6)
C1	0.0902 (4)	1.0862 (3)	0.70951 (15)	0.0566 (9)
C2	0.1044 (4)	1.1357 (3)	0.65067 (14)	0.0463 (8)
C3	0.0605 (4)	1.2523 (3)	0.64682 (16)	0.0607 (9)
H3A	0.0690	1.2880	0.6081	0.073*
C4	0.0045 (5)	1.3162 (4)	0.6992 (2)	0.0762 (11)
H4	−0.0224	1.3948	0.6960	0.091*
C5	−0.0114 (5)	1.2632 (5)	0.7562 (2)	0.0841 (13)
H5	−0.0512	1.3057	0.7913	0.101*
C6	0.0306 (5)	1.1495 (4)	0.76173 (17)	0.0767 (12)
H6A	0.0192	1.1141	0.8005	0.092*
C7	0.1671 (4)	1.0702 (3)	0.59493 (14)	0.0480 (8)
H7	0.1953	0.9918	0.5973	0.058*
C8	0.2777 (4)	1.1187 (3)	0.43966 (14)	0.0434 (7)
C9	0.4020 (4)	0.8808 (3)	0.34211 (15)	0.0499 (8)
H9	0.4075	0.9231	0.3054	0.060*
C10	0.4389 (4)	0.7564 (3)	0.33816 (14)	0.0455 (8)
C11	0.4785 (4)	0.6972 (3)	0.28059 (15)	0.0515 (8)
C12	0.5155 (5)	0.5792 (3)	0.27706 (19)	0.0674 (10)
H12	0.5434	0.5420	0.2383	0.081*
C13	0.5112 (5)	0.5166 (4)	0.3307 (2)	0.0785 (12)
H13	0.5351	0.4364	0.3283	0.094*
C14	0.4719 (5)	0.5714 (3)	0.3881 (2)	0.0758 (11)
H14	0.4688	0.5284	0.4245	0.091*
C15	0.4369 (4)	0.6898 (3)	0.39182 (16)	0.0596 (9)
H15	0.4114	0.7265	0.4311	0.072*
C16	−0.0109 (4)	0.4711 (3)	0.11266 (15)	0.0498 (8)
C17	−0.0726 (4)	0.3890 (3)	0.15659 (14)	0.0444 (8)
C18	−0.2529 (5)	0.3556 (3)	0.16078 (16)	0.0599 (9)
H18	−0.2967	0.3019	0.1907	0.072*
C19	−0.3681 (5)	0.4010 (4)	0.12104 (19)	0.0719 (11)
H19	−0.4891	0.3765	0.1235	0.086*
C20	−0.3039 (6)	0.4819 (4)	0.07809 (18)	0.0759 (12)
H20	−0.3819	0.5130	0.0516	0.091*
C21	−0.1245 (5)	0.5180 (3)	0.07351 (16)	0.0667 (10)
H21	−0.0814	0.5735	0.0443	0.080*
C22	0.0461 (4)	0.3399 (3)	0.20069 (14)	0.0443 (8)
C23	0.2465 (4)	0.2311 (3)	0.23466 (14)	0.0460 (8)
C24	0.2022 (4)	0.1161 (3)	0.10273 (14)	0.0486 (8)
H24	0.2049	0.0624	0.1346	0.058*
C25	0.2301 (4)	0.0749 (3)	0.03672 (14)	0.0479 (8)
C26	0.2425 (4)	−0.0464 (3)	0.01809 (15)	0.0561 (9)
C27	0.2720 (5)	−0.0836 (4)	−0.0444 (2)	0.0790 (12)
H27	0.2803	−0.1657	−0.0561	0.095*
C28	0.2890 (6)	0.0012 (5)	−0.08861 (19)	0.0903 (14)
H28	0.3108	−0.0233	−0.1306	0.108*
C29	0.2744 (6)	0.1223 (5)	−0.07193 (18)	0.0872 (13)
H29	0.2839	0.1789	−0.1027	0.105*
C30	0.2458 (5)	0.1594 (3)	−0.00994 (15)	0.0651 (10)
H30	0.2366	0.2415	0.0013	0.078*
C31	0.1607 (8)	0.5962 (6)	0.5595 (4)	0.192 (4)
H31A	0.0341	0.5822	0.5574	0.288*
H31B	0.2023	0.5618	0.5966	0.288*
H31C	0.2014	0.5572	0.5217	0.288*
C32	0.2229 (7)	0.7192 (6)	0.5636 (3)	0.137 (2)
H32A	0.3501	0.7290	0.5621	0.164*
H32B	0.1986	0.7524	0.6060	0.164*

	U11	U22	U33	U12	U13	U23
S1	0.0842 (7)	0.0466 (5)	0.0462 (5)	0.0223 (5)	0.0086 (4)	0.0072 (4)
S2	0.0711 (6)	0.0711 (6)	0.0526 (5)	0.0330 (5)	0.0123 (5)	0.0211 (5)
Cl1	0.1144 (9)	0.0774 (7)	0.0609 (6)	0.0123 (6)	0.0128 (6)	0.0226 (5)
Cl2	0.0862 (7)	0.0867 (7)	0.0473 (5)	0.0142 (6)	0.0118 (5)	−0.0027 (5)
Cl3	0.0576 (6)	0.0654 (6)	0.0864 (7)	0.0088 (5)	0.0044 (5)	0.0266 (5)
Cl4	0.1162 (9)	0.0531 (6)	0.0935 (8)	0.0272 (6)	0.0055 (6)	0.0064 (5)
O1	0.086 (2)	0.0733 (18)	0.099 (2)	0.0229 (17)	0.0189 (17)	0.0211 (16)
N1	0.0572 (18)	0.0483 (16)	0.0421 (15)	0.0134 (13)	0.0085 (13)	0.0011 (13)
N2	0.0617 (18)	0.0441 (15)	0.0402 (14)	0.0176 (13)	0.0103 (13)	0.0080 (12)
N3	0.0725 (19)	0.0443 (16)	0.0391 (14)	0.0180 (14)	0.0112 (13)	0.0080 (12)
N4	0.0585 (18)	0.0404 (15)	0.0442 (15)	0.0139 (13)	0.0096 (13)	0.0052 (12)
N5	0.071 (2)	0.0499 (17)	0.0428 (15)	0.0239 (15)	0.0053 (14)	0.0018 (13)
N6	0.073 (2)	0.0553 (17)	0.0381 (15)	0.0198 (15)	0.0002 (14)	0.0066 (13)
N7	0.0568 (17)	0.0475 (16)	0.0378 (14)	0.0186 (13)	0.0076 (13)	0.0071 (12)
N8	0.0552 (17)	0.0499 (17)	0.0374 (14)	0.0180 (13)	0.0080 (12)	0.0049 (12)
C1	0.049 (2)	0.070 (2)	0.0462 (19)	0.0005 (18)	0.0070 (16)	−0.0004 (18)
C2	0.0424 (19)	0.050 (2)	0.0436 (18)	0.0020 (16)	0.0050 (15)	−0.0025 (16)
C3	0.059 (2)	0.066 (2)	0.056 (2)	0.0138 (19)	0.0020 (18)	−0.0050 (19)
C4	0.069 (3)	0.074 (3)	0.084 (3)	0.021 (2)	0.003 (2)	−0.021 (2)
C5	0.072 (3)	0.108 (4)	0.068 (3)	0.016 (3)	0.019 (2)	−0.027 (3)
C6	0.077 (3)	0.101 (3)	0.046 (2)	0.002 (3)	0.016 (2)	−0.005 (2)
C7	0.052 (2)	0.0485 (19)	0.0436 (18)	0.0088 (16)	0.0053 (15)	0.0021 (16)
C8	0.0454 (19)	0.0458 (19)	0.0402 (17)	0.0115 (15)	0.0025 (14)	0.0045 (15)
C9	0.059 (2)	0.047 (2)	0.0444 (18)	0.0098 (17)	0.0050 (16)	0.0072 (16)
C10	0.047 (2)	0.0381 (18)	0.0503 (19)	0.0071 (15)	0.0035 (15)	−0.0002 (15)
C11	0.045 (2)	0.053 (2)	0.055 (2)	0.0086 (16)	−0.0013 (16)	−0.0042 (17)
C12	0.065 (3)	0.058 (2)	0.077 (3)	0.016 (2)	0.001 (2)	−0.017 (2)
C13	0.081 (3)	0.048 (2)	0.107 (3)	0.021 (2)	−0.008 (3)	−0.004 (2)
C14	0.092 (3)	0.054 (2)	0.083 (3)	0.019 (2)	−0.007 (2)	0.013 (2)
C15	0.070 (3)	0.049 (2)	0.061 (2)	0.0120 (18)	0.0052 (19)	0.0037 (18)
C16	0.050 (2)	0.050 (2)	0.0506 (19)	0.0145 (16)	−0.0002 (16)	−0.0009 (16)
C17	0.055 (2)	0.0372 (17)	0.0430 (17)	0.0168 (16)	0.0058 (15)	−0.0046 (14)
C18	0.060 (2)	0.059 (2)	0.063 (2)	0.0171 (19)	0.0163 (19)	−0.0038 (18)
C19	0.052 (2)	0.081 (3)	0.084 (3)	0.023 (2)	0.003 (2)	−0.007 (2)
C20	0.071 (3)	0.096 (3)	0.069 (3)	0.042 (3)	−0.009 (2)	0.003 (2)
C21	0.072 (3)	0.078 (3)	0.058 (2)	0.031 (2)	0.002 (2)	0.018 (2)
C22	0.052 (2)	0.0393 (18)	0.0441 (18)	0.0124 (15)	0.0102 (15)	0.0049 (15)
C23	0.057 (2)	0.0432 (18)	0.0390 (17)	0.0106 (16)	0.0048 (15)	0.0058 (15)
C24	0.060 (2)	0.047 (2)	0.0419 (18)	0.0171 (17)	0.0053 (16)	0.0078 (15)
C25	0.049 (2)	0.055 (2)	0.0431 (18)	0.0173 (16)	0.0067 (15)	0.0044 (16)
C26	0.056 (2)	0.059 (2)	0.054 (2)	0.0198 (18)	−0.0012 (17)	−0.0064 (18)
C27	0.081 (3)	0.083 (3)	0.073 (3)	0.030 (2)	0.003 (2)	−0.025 (2)
C28	0.092 (3)	0.130 (4)	0.048 (2)	0.031 (3)	0.006 (2)	−0.023 (3)
C29	0.106 (4)	0.114 (4)	0.048 (2)	0.030 (3)	0.021 (2)	0.015 (2)
C30	0.078 (3)	0.073 (3)	0.051 (2)	0.027 (2)	0.0156 (19)	0.0117 (19)
C31	0.122 (5)	0.109 (5)	0.359 (11)	0.040 (4)	−0.016 (6)	0.079 (6)
C32	0.084 (4)	0.125 (5)	0.211 (7)	0.027 (4)	−0.004 (4)	0.056 (5)

S1—C8	1.682 (3)	C10—C11	1.394 (4)
S2—C23	1.669 (3)	C11—C12	1.373 (4)
Cl1—C1	1.735 (4)	C12—C13	1.364 (5)
Cl2—C11	1.739 (3)	C12—H12	0.93
Cl3—C16	1.730 (3)	C13—C14	1.370 (5)
Cl4—C26	1.732 (3)	C13—H13	0.93
O1—C32	1.380 (5)	C14—C15	1.371 (4)
O1—H1	0.82	C14—H14	0.93
N1—C7	1.267 (3)	C15—H15	0.93
N1—N2	1.373 (3)	C16—C21	1.371 (4)
N2—C8	1.341 (3)	C16—C17	1.383 (4)
N2—H2	0.86	C17—C18	1.383 (4)
N3—C8	1.338 (3)	C17—C22	1.474 (4)
N3—N4	1.372 (3)	C18—C19	1.378 (5)
N3—H3	0.86	C18—H18	0.93
N4—C9	1.279 (3)	C19—C20	1.365 (5)
N5—C22	1.294 (3)	C19—H19	0.93
N5—N6	1.370 (3)	C20—C21	1.381 (5)
N6—C23	1.340 (3)	C20—H20	0.93
N6—H6	0.86	C21—H21	0.93
N7—C23	1.378 (3)	C24—C25	1.457 (4)
N7—C22	1.382 (3)	C24—H24	0.93
N7—N8	1.396 (3)	C25—C26	1.380 (4)
N8—C24	1.267 (3)	C25—C30	1.398 (4)
C1—C6	1.385 (4)	C26—C27	1.379 (5)
C1—C2	1.389 (4)	C27—C28	1.363 (5)
C2—C3	1.390 (4)	C27—H27	0.93
C2—C7	1.463 (4)	C28—C29	1.374 (6)
C3—C4	1.379 (4)	C28—H28	0.93
C3—H3A	0.93	C29—C30	1.368 (5)
C4—C5	1.372 (5)	C29—H29	0.93
C4—H4	0.93	C30—H30	0.93
C5—C6	1.358 (5)	C31—C32	1.350 (7)
C5—H5	0.93	C31—H31A	0.96
C6—H6A	0.93	C31—H31B	0.96
C7—H7	0.93	C31—H31C	0.96
C9—C10	1.441 (4)	C32—H32A	0.97
C9—H9	0.93	C32—H32B	0.97
C10—C15	1.391 (4)
C32—O1—H1	109.5	C14—C15—H15	119.3
C7—N1—N2	116.9 (2)	C10—C15—H15	119.3
C8—N2—N1	117.8 (2)	C21—C16—C17	121.3 (3)
C8—N2—H2	121.1	C21—C16—Cl3	118.6 (3)
N1—N2—H2	121.1	C17—C16—Cl3	120.0 (2)
C8—N3—N4	121.6 (2)	C16—C17—C18	118.5 (3)
C8—N3—H3	119.2	C16—C17—C22	122.6 (3)
N4—N3—H3	119.2	C18—C17—C22	118.9 (3)
C9—N4—N3	114.8 (2)	C19—C18—C17	120.7 (3)
C22—N5—N6	103.9 (2)	C19—C18—H18	119.7
C23—N6—N5	114.6 (2)	C17—C18—H18	119.7
C23—N6—H6	122.7	C20—C19—C18	119.7 (4)
N5—N6—H6	122.7	C20—C19—H19	120.1
C23—N7—C22	108.6 (2)	C18—C19—H19	120.1
C23—N7—N8	129.7 (2)	C19—C20—C21	120.8 (4)
C22—N7—N8	121.5 (2)	C19—C20—H20	119.6
C24—N8—N7	116.3 (2)	C21—C20—H20	119.6
C6—C1—C2	121.3 (3)	C16—C21—C20	119.1 (3)
C6—C1—Cl1	118.1 (3)	C16—C21—H21	120.5
C2—C1—Cl1	120.6 (2)	C20—C21—H21	120.5
C3—C2—C1	117.3 (3)	N5—C22—N7	110.7 (3)
C3—C2—C7	120.6 (3)	N5—C22—C17	125.3 (3)
C1—C2—C7	122.1 (3)	N7—C22—C17	123.9 (3)
C4—C3—C2	121.3 (3)	N6—C23—N7	102.1 (2)
C4—C3—H3A	119.3	N6—C23—S2	127.3 (2)
C2—C3—H3A	119.3	N7—C23—S2	130.5 (2)
C5—C4—C3	119.6 (4)	N8—C24—C25	119.9 (3)
C5—C4—H4	120.2	N8—C24—H24	120.0
C3—C4—H4	120.2	C25—C24—H24	120.0
C6—C5—C4	120.6 (4)	C26—C25—C30	118.0 (3)
C6—C5—H5	119.7	C26—C25—C24	122.0 (3)
C4—C5—H5	119.7	C30—C25—C24	120.0 (3)
C5—C6—C1	119.8 (4)	C27—C26—C25	121.4 (3)
C5—C6—H6A	120.1	C27—C26—Cl4	118.0 (3)
C1—C6—H6A	120.1	C25—C26—Cl4	120.6 (2)
N1—C7—C2	118.5 (3)	C28—C27—C26	119.3 (4)
N1—C7—H7	120.8	C28—C27—H27	120.3
C2—C7—H7	120.8	C26—C27—H27	120.3
N3—C8—N2	116.5 (3)	C27—C28—C29	120.8 (4)
N3—C8—S1	119.8 (2)	C27—C28—H28	119.6
N2—C8—S1	123.7 (2)	C29—C28—H28	119.6
N4—C9—C10	122.2 (3)	C30—C29—C28	119.9 (4)
N4—C9—H9	118.9	C30—C29—H29	120.0
C10—C9—H9	118.9	C28—C29—H29	120.0
C15—C10—C11	116.9 (3)	C29—C30—C25	120.6 (4)
C15—C10—C9	121.4 (3)	C29—C30—H30	119.7
C11—C10—C9	121.7 (3)	C25—C30—H30	119.7
C12—C11—C10	121.6 (3)	C32—C31—H31A	109.5
C12—C11—Cl2	118.3 (3)	C32—C31—H31B	109.5
C10—C11—Cl2	120.1 (2)	H31A—C31—H31B	109.5
C13—C12—C11	119.8 (3)	C32—C31—H31C	109.5
C13—C12—H12	120.1	H31A—C31—H31C	109.5
C11—C12—H12	120.1	H31B—C31—H31C	109.5
C12—C13—C14	120.3 (4)	C31—C32—O1	122.3 (6)
C12—C13—H13	119.8	C31—C32—H32A	106.8
C14—C13—H13	119.8	O1—C32—H32A	106.8
C13—C14—C15	120.0 (4)	C31—C32—H32B	106.8
C13—C14—H14	120.0	O1—C32—H32B	106.8
C15—C14—H14	120.0	H32A—C32—H32B	106.6
C14—C15—C10	121.4 (3)
C7—N1—N2—C8	−173.4 (3)	C21—C16—C17—C22	−178.1 (3)
C8—N3—N4—C9	174.7 (3)	Cl3—C16—C17—C22	−1.6 (4)
C22—N5—N6—C23	−1.1 (4)	C16—C17—C18—C19	1.4 (5)
C23—N7—N8—C24	38.7 (4)	C22—C17—C18—C19	179.0 (3)
C22—N7—N8—C24	−147.1 (3)	C17—C18—C19—C20	−1.4 (5)
C6—C1—C2—C3	1.5 (5)	C18—C19—C20—C21	0.6 (6)
Cl1—C1—C2—C3	−176.9 (2)	C17—C16—C21—C20	−0.3 (5)
C6—C1—C2—C7	−180.0 (3)	Cl3—C16—C21—C20	−176.8 (3)
Cl1—C1—C2—C7	1.6 (4)	C19—C20—C21—C16	0.3 (6)
C1—C2—C3—C4	−0.2 (5)	N6—N5—C22—N7	2.1 (3)
C7—C2—C3—C4	−178.8 (3)	N6—N5—C22—C17	178.9 (3)
C2—C3—C4—C5	−1.1 (6)	C23—N7—C22—N5	−2.5 (4)
C3—C4—C5—C6	1.2 (6)	N8—N7—C22—N5	−177.7 (3)
C4—C5—C6—C1	0.1 (6)	C23—N7—C22—C17	−179.3 (3)
C2—C1—C6—C5	−1.5 (6)	N8—N7—C22—C17	5.5 (4)
Cl1—C1—C6—C5	176.9 (3)	C16—C17—C22—N5	115.1 (4)
N2—N1—C7—C2	178.9 (3)	C18—C17—C22—N5	−62.5 (4)
C3—C2—C7—N1	0.7 (5)	C16—C17—C22—N7	−68.6 (4)
C1—C2—C7—N1	−177.7 (3)	C18—C17—C22—N7	113.9 (3)
N4—N3—C8—N2	−2.2 (4)	N5—N6—C23—N7	−0.4 (3)
N4—N3—C8—S1	176.7 (2)	N5—N6—C23—S2	176.6 (2)
N1—N2—C8—N3	−178.5 (3)	C22—N7—C23—N6	1.6 (3)
N1—N2—C8—S1	2.6 (4)	N8—N7—C23—N6	176.4 (3)
N3—N4—C9—C10	178.8 (3)	C22—N7—C23—S2	−175.2 (3)
N4—C9—C10—C15	−1.7 (5)	N8—N7—C23—S2	−0.5 (5)
N4—C9—C10—C11	178.5 (3)	N7—N8—C24—C25	−177.3 (3)
C15—C10—C11—C12	−0.6 (5)	N8—C24—C25—C26	−173.1 (3)
C9—C10—C11—C12	179.3 (3)	N8—C24—C25—C30	7.1 (5)
C15—C10—C11—Cl2	−179.8 (2)	C30—C25—C26—C27	1.0 (5)
C9—C10—C11—Cl2	0.1 (4)	C24—C25—C26—C27	−178.8 (3)
C10—C11—C12—C13	1.0 (5)	C30—C25—C26—Cl4	−179.9 (3)
Cl2—C11—C12—C13	−179.8 (3)	C24—C25—C26—Cl4	0.3 (4)
C11—C12—C13—C14	−0.6 (6)	C25—C26—C27—C28	−0.2 (6)
C12—C13—C14—C15	−0.1 (6)	Cl4—C26—C27—C28	−179.3 (3)
C13—C14—C15—C10	0.6 (6)	C26—C27—C28—C29	−1.0 (7)
C11—C10—C15—C14	−0.2 (5)	C27—C28—C29—C30	1.3 (7)
C9—C10—C15—C14	179.9 (3)	C28—C29—C30—C25	−0.4 (6)
C21—C16—C17—C18	−0.5 (5)	C26—C25—C30—C29	−0.7 (5)
Cl3—C16—C17—C18	175.9 (2)	C24—C25—C30—C29	179.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	2.20	2.978 (4)	150
N6—H6···S1i	0.86	2.41	3.261 (3)	170
N3—H3···S2ii	0.86	2.56	3.410 (2)	169
O1—H1···S1iii	0.82	2.65	3.413 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86	2.20	2.978 (4)	150
N6—H6⋯S1i	0.86	2.41	3.261 (3)	170
N3—H3⋯S2ii	0.86	2.56	3.410 (2)	169
O1—H1⋯S1iii	0.82	2.65	3.413 (3)	156

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