Chloridodiphen-yl{[1-(1,3-thia-zol-2-yl-κN)ethyl-idene]-4-phenyl-thio-semicarbazidato-κN,S}tin(IV) methanol monosolvate.

The title compound, [Sn(C(6)H(5))(2)(C(12)H(11)N(4)S(2))Cl]·CH(4)O, is formed during the reaction between 2-acetyl-thia-zole 4-phenyl-thio-semicarbazone (Hacthptsc) and diphenyl-tin(IV) dichloride in methanol. In the crystal structure, the Sn atom exhibits an octa-hedral geometry with the [N(2)S] anionic tridentate thio-semicarbazone ligand having chloride trans to the central N and the two phenyl groups trans to each other. The Sn-Cl distance is 2.5929 (6), Sn-S is 2.4896 (6) and Sn-N to the central N is 2.3220 (16) Å. The MeOH mol-ecules link the Sn complexes into one-dimensional chains via N-H⋯O and O-H⋯Cl hydrogen bonds.

Related literature

For the biological activity and structural characteristics of tin compounds of thio­semicarbazones, see: Teoh et al. (1999 ▶); Gielen et al. (2005 ▶); Chaudhary et al. (2009 ▶); Bamgboye & Bamgboye (1988 ▶); Barberi et al. (1993 ▶); Casas et al. (1994 ▶, 1996 ▶, 1997 ▶); De Sousa et al. (2001 ▶); Li et al. (2011 ▶); Macias et al. (1989 ▶); Huheey et al. (1993 ▶). For related structures, see: Venkatraman et al. (2004 ▶, 2007 ▶, 2009 ▶); Swesi et al. (2006a ▶,b ▶,c ▶); Sreekanth & Kurup (2004 ▶); Mendes et al. (2008 ▶); Li et al. (2011 ▶). For standard bond lengths, see: Allen et al. (1979 ▶); Davies (1998 ▶); Dey et al. (2003 ▶). For graph-set analysis, see: Etter (1990 ▶).

Experimental

Crystal data

[Sn(C6H5)2(C12H11N4S2)Cl]·CH4O

M = 615.75

Monoclinic,

a = 8.5971 (10) Å

b = 20.182 (3) Å

c = 15.794 (2) Å

β = 102.050 (7)°

V = 2680.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.23 mm−1

T = 297 K

0.30 × 0.20 × 0.17 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.709, T max = 0.818

31922 measured reflections

8479 independent reflections

6194 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.070

S = 1.01

8479 reflections

316 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.58 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037627/zk2029sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037627/zk2029Isup2.hkl

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

[Sn(C6H5)2(C12H11N4S2)Cl]·CH4O	F(000) = 1240
Mr = 615.75	Dx = 1.526 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7958 reflections
a = 8.5971 (10) Å	θ = 2.5–32.0°
b = 20.182 (3) Å	µ = 1.23 mm−1
c = 15.794 (2) Å	T = 297 K
β = 102.050 (7)°	Fragment, yellow
V = 2680.0 (6) Å3	0.30 × 0.20 × 0.17 mm
Z = 4

Nonius KappaCCD diffractometer	8479 independent reflections
Radiation source: fine-focus sealed tube	6194 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω and φ scans	θmax = 32.0°, θmin = 2.6°
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	h = −12→12
Tmin = 0.709, Tmax = 0.818	k = −28→25
31922 measured reflections	l = −23→23

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.070	w = 1/[σ2(Fo2) + (0.0236P)2 + 0.9273P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.002
8479 reflections	Δρmax = 0.35 e Å−3
316 parameters	Δρmin = −0.58 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00176 (19)

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
Sn1	0.400041 (15)	0.263309 (7)	0.526902 (8)	0.03515 (5)
Cl1	0.66803 (7)	0.21480 (4)	0.50486 (4)	0.06294 (17)
S1	0.35758 (7)	0.31789 (3)	0.38254 (3)	0.04796 (14)
S2	0.09795 (9)	0.29250 (4)	0.75637 (4)	0.06512 (19)
N1	0.17015 (18)	0.32507 (8)	0.52098 (10)	0.0356 (4)
N2	0.10480 (19)	0.36198 (9)	0.44956 (11)	0.0403 (4)
N3	0.2829 (2)	0.24841 (9)	0.66321 (12)	0.0419 (4)
N4	0.1258 (2)	0.39796 (10)	0.31437 (12)	0.0426 (4)
H4N	0.175 (3)	0.3937 (12)	0.2732 (15)	0.051*
C1	0.1632 (2)	0.28859 (11)	0.66081 (13)	0.0396 (4)
C2	0.2388 (3)	0.23643 (14)	0.80026 (17)	0.0615 (7)
H2	0.2540	0.2202	0.8565	0.074*
C3	0.3249 (3)	0.21897 (13)	0.74245 (15)	0.0540 (6)
H3	0.4080	0.1887	0.7554	0.065*
C4	0.0950 (2)	0.32769 (11)	0.58439 (13)	0.0402 (5)
C5	−0.0537 (3)	0.36652 (15)	0.58116 (17)	0.0617 (7)
H5A	−0.0412	0.4101	0.5590	0.092*
H5B	−0.0746	0.3700	0.6384	0.092*
H5C	−0.1410	0.3445	0.5440	0.092*
C6	0.1826 (2)	0.36139 (10)	0.38687 (13)	0.0367 (4)
C7	−0.0056 (2)	0.44193 (11)	0.29689 (14)	0.0430 (5)
C8	−0.0943 (4)	0.46150 (16)	0.35598 (19)	0.0756 (9)
H8	−0.0706	0.4451	0.4122	0.091*
C9	−0.2185 (4)	0.50555 (18)	0.3312 (2)	0.0845 (10)
H9	−0.2779	0.5181	0.3715	0.101*
C10	−0.2564 (3)	0.53100 (16)	0.2506 (2)	0.0739 (8)
H10	−0.3395	0.5611	0.2354	0.089*
C11	−0.1695 (3)	0.51142 (17)	0.1920 (2)	0.0796 (9)
H11	−0.1941	0.5281	0.1360	0.096*
C12	−0.0455 (3)	0.46717 (15)	0.21483 (17)	0.0631 (7)
H12	0.0118	0.4543	0.1738	0.076*
C13	0.2818 (3)	0.17040 (12)	0.49558 (13)	0.0445 (5)
C14	0.1166 (3)	0.16993 (15)	0.47549 (18)	0.0676 (8)
H14	0.0612	0.2091	0.4787	0.081*
C15	0.0335 (4)	0.11204 (19)	0.4508 (2)	0.0847 (10)
H15	−0.0771	0.1127	0.4377	0.102*
C16	0.1118 (5)	0.05441 (17)	0.4454 (2)	0.0839 (10)
H16	0.0553	0.0156	0.4288	0.101*
C17	0.2748 (5)	0.05366 (15)	0.4646 (2)	0.0842 (10)
H17	0.3289	0.0142	0.4609	0.101*
C18	0.3598 (4)	0.11156 (13)	0.48954 (17)	0.0652 (7)
H18	0.4704	0.1105	0.5023	0.078*
C19	0.5337 (2)	0.33492 (11)	0.61156 (13)	0.0408 (5)
C20	0.6194 (3)	0.31871 (15)	0.69410 (15)	0.0557 (6)
H20	0.6246	0.2749	0.7127	0.067*
C21	0.6963 (3)	0.36751 (19)	0.74819 (17)	0.0714 (9)
H21	0.7518	0.3564	0.8034	0.086*
C22	0.6916 (3)	0.43192 (19)	0.7215 (2)	0.0784 (10)
H22	0.7428	0.4645	0.7588	0.094*
C23	0.6124 (3)	0.44858 (15)	0.6407 (2)	0.0732 (8)
H23	0.6114	0.4924	0.6223	0.088*
C24	0.5321 (3)	0.39994 (13)	0.58489 (17)	0.0544 (6)
H24	0.4776	0.4116	0.5297	0.065*
O1	0.2782 (3)	0.38699 (13)	0.16545 (14)	0.0795 (7)
H1S	0.252 (5)	0.357 (2)	0.137 (3)	0.119*
C25	0.4439 (4)	0.38909 (18)	0.1816 (2)	0.0845 (10)
H25A	0.4819	0.4219	0.2250	0.127*
H25B	0.4780	0.4003	0.1292	0.127*
H25C	0.4860	0.3465	0.2016	0.127*

	U11	U22	U33	U12	U13	U23
Sn1	0.03442 (8)	0.03828 (8)	0.03287 (8)	0.00389 (6)	0.00732 (5)	−0.00039 (6)
Cl1	0.0524 (3)	0.0723 (4)	0.0704 (4)	0.0224 (3)	0.0273 (3)	0.0048 (3)
S1	0.0483 (3)	0.0618 (4)	0.0370 (3)	0.0164 (3)	0.0163 (2)	0.0096 (2)
S2	0.0809 (4)	0.0739 (5)	0.0516 (4)	0.0144 (4)	0.0391 (3)	0.0095 (3)
N1	0.0337 (8)	0.0375 (9)	0.0366 (9)	0.0025 (7)	0.0096 (7)	0.0025 (7)
N2	0.0351 (8)	0.0463 (11)	0.0394 (9)	0.0050 (7)	0.0072 (7)	0.0068 (8)
N3	0.0436 (9)	0.0452 (11)	0.0387 (10)	0.0031 (8)	0.0129 (8)	0.0029 (7)
N4	0.0435 (10)	0.0478 (11)	0.0363 (10)	0.0051 (8)	0.0078 (8)	0.0054 (8)
C1	0.0424 (10)	0.0421 (11)	0.0380 (11)	−0.0025 (9)	0.0171 (9)	−0.0008 (9)
C2	0.0757 (17)	0.0685 (18)	0.0436 (13)	0.0027 (14)	0.0202 (12)	0.0133 (12)
C3	0.0571 (14)	0.0582 (16)	0.0458 (13)	0.0055 (12)	0.0089 (11)	0.0108 (11)
C4	0.0361 (10)	0.0438 (12)	0.0431 (11)	−0.0001 (9)	0.0137 (9)	0.0022 (9)
C5	0.0471 (13)	0.0786 (19)	0.0665 (17)	0.0212 (13)	0.0285 (12)	0.0139 (14)
C6	0.0356 (10)	0.0370 (11)	0.0359 (10)	−0.0009 (8)	0.0038 (8)	0.0009 (8)
C7	0.0411 (11)	0.0379 (12)	0.0463 (12)	−0.0010 (9)	0.0004 (9)	0.0034 (10)
C8	0.086 (2)	0.079 (2)	0.0632 (18)	0.0403 (17)	0.0187 (15)	0.0179 (15)
C9	0.084 (2)	0.088 (2)	0.083 (2)	0.0415 (18)	0.0211 (17)	0.0145 (19)
C10	0.0612 (16)	0.0656 (19)	0.085 (2)	0.0173 (14)	−0.0066 (15)	0.0078 (16)
C11	0.0730 (19)	0.090 (2)	0.0663 (19)	0.0237 (17)	−0.0076 (15)	0.0245 (17)
C12	0.0585 (14)	0.0755 (19)	0.0516 (15)	0.0139 (13)	0.0030 (12)	0.0135 (13)
C13	0.0581 (13)	0.0454 (13)	0.0306 (10)	−0.0060 (10)	0.0104 (9)	−0.0026 (9)
C14	0.0623 (16)	0.0642 (18)	0.080 (2)	−0.0180 (13)	0.0245 (14)	−0.0305 (15)
C15	0.083 (2)	0.093 (3)	0.084 (2)	−0.041 (2)	0.0294 (17)	−0.0394 (19)
C16	0.129 (3)	0.066 (2)	0.0580 (18)	−0.045 (2)	0.0219 (19)	−0.0142 (15)
C17	0.143 (3)	0.0404 (16)	0.0615 (19)	−0.0015 (18)	0.0033 (19)	−0.0003 (13)
C18	0.0880 (19)	0.0441 (15)	0.0547 (15)	0.0070 (14)	−0.0050 (13)	0.0002 (12)
C19	0.0299 (9)	0.0526 (14)	0.0417 (11)	−0.0009 (9)	0.0115 (8)	−0.0092 (10)
C20	0.0470 (12)	0.0766 (18)	0.0439 (13)	−0.0096 (12)	0.0106 (10)	−0.0023 (12)
C21	0.0528 (15)	0.119 (3)	0.0429 (14)	−0.0235 (16)	0.0124 (11)	−0.0221 (16)
C22	0.0642 (17)	0.098 (3)	0.077 (2)	−0.0290 (17)	0.0238 (16)	−0.0406 (19)
C23	0.0661 (17)	0.0568 (18)	0.098 (2)	−0.0130 (14)	0.0212 (16)	−0.0207 (16)
C24	0.0479 (12)	0.0528 (15)	0.0614 (15)	0.0000 (11)	0.0089 (11)	−0.0047 (12)
O1	0.0758 (14)	0.1003 (19)	0.0638 (14)	0.0098 (13)	0.0178 (11)	−0.0101 (11)
C25	0.084 (2)	0.095 (3)	0.080 (2)	−0.0011 (19)	0.0276 (17)	0.0158 (18)

Sn1—C19	2.134 (2)	C10—H10	0.9300
Sn1—C13	2.141 (2)	C11—C12	1.379 (4)
Sn1—N1	2.3220 (16)	C11—H11	0.9300
Sn1—S1	2.4896 (6)	C12—H12	0.9300
Sn1—N3	2.5779 (18)	C13—C18	1.377 (3)
Sn1—Cl1	2.5929 (6)	C13—C14	1.389 (3)
S1—C6	1.755 (2)	C14—C15	1.383 (4)
S2—C2	1.696 (3)	C14—H14	0.9300
S2—C1	1.718 (2)	C15—C16	1.355 (5)
N1—C4	1.301 (2)	C15—H15	0.9300
N1—N2	1.371 (2)	C16—C17	1.371 (5)
N2—C6	1.306 (2)	C16—H16	0.9300
N3—C1	1.304 (3)	C17—C18	1.391 (4)
N3—C3	1.364 (3)	C17—H17	0.9300
N4—C6	1.364 (3)	C18—H18	0.9300
N4—C7	1.418 (3)	C19—C24	1.377 (3)
N4—H4N	0.85 (2)	C19—C20	1.396 (3)
C1—C4	1.459 (3)	C20—C21	1.379 (4)
C2—C3	1.337 (3)	C20—H20	0.9300
C2—H2	0.9300	C21—C22	1.364 (5)
C3—H3	0.9300	C21—H21	0.9300
C4—C5	1.491 (3)	C22—C23	1.358 (4)
C5—H5A	0.9600	C22—H22	0.9300
C5—H5B	0.9600	C23—C24	1.401 (4)
C5—H5C	0.9600	C23—H23	0.9300
C7—C12	1.368 (3)	C24—H24	0.9300
C7—C8	1.380 (3)	O1—C25	1.395 (4)
C8—C9	1.382 (4)	O1—H1S	0.76 (4)
C8—H8	0.9300	C25—H25A	0.9600
C9—C10	1.348 (4)	C25—H25B	0.9600
C9—H9	0.9300	C25—H25C	0.9600
C10—C11	1.363 (4)
C19—Sn1—C13	154.86 (8)	C10—C9—H9	118.9
C19—Sn1—N1	90.24 (7)	C8—C9—H9	118.9
C13—Sn1—N1	95.85 (8)	C9—C10—C11	118.1 (3)
C19—Sn1—S1	103.35 (6)	C9—C10—H10	120.9
C13—Sn1—S1	101.78 (6)	C11—C10—H10	120.9
N1—Sn1—S1	76.39 (4)	C10—C11—C12	120.9 (3)
C19—Sn1—N3	78.98 (7)	C10—C11—H11	119.5
C13—Sn1—N3	80.88 (7)	C12—C11—H11	119.5
N1—Sn1—N3	67.57 (6)	C7—C12—C11	121.0 (3)
S1—Sn1—N3	143.93 (4)	C7—C12—H12	119.5
C19—Sn1—Cl1	87.85 (5)	C11—C12—H12	119.5
C13—Sn1—Cl1	91.74 (6)	C18—C13—C14	117.9 (2)
N1—Sn1—Cl1	165.94 (4)	C18—C13—Sn1	123.85 (18)
S1—Sn1—Cl1	90.49 (2)	C14—C13—Sn1	118.16 (19)
N3—Sn1—Cl1	125.54 (4)	C15—C14—C13	120.9 (3)
C6—S1—Sn1	98.55 (7)	C15—C14—H14	119.5
C2—S2—C1	89.55 (12)	C13—C14—H14	119.5
C4—N1—N2	115.29 (16)	C16—C15—C14	120.6 (3)
C4—N1—Sn1	123.10 (14)	C16—C15—H15	119.7
N2—N1—Sn1	121.61 (11)	C14—C15—H15	119.7
C6—N2—N1	115.61 (16)	C15—C16—C17	119.6 (3)
C1—N3—C3	110.72 (19)	C15—C16—H16	120.2
C1—N3—Sn1	110.27 (13)	C17—C16—H16	120.2
C3—N3—Sn1	137.91 (15)	C16—C17—C18	120.4 (3)
C6—N4—C7	129.29 (18)	C16—C17—H17	119.8
C6—N4—H4N	115.9 (16)	C18—C17—H17	119.8
C7—N4—H4N	114.8 (16)	C13—C18—C17	120.6 (3)
N3—C1—C4	122.62 (17)	C13—C18—H18	119.7
N3—C1—S2	113.78 (16)	C17—C18—H18	119.7
C4—C1—S2	123.59 (16)	C24—C19—C20	118.6 (2)
C3—C2—S2	110.3 (2)	C24—C19—Sn1	118.94 (17)
C3—C2—H2	124.9	C20—C19—Sn1	122.45 (19)
S2—C2—H2	124.9	C21—C20—C19	120.2 (3)
C2—C3—N3	115.7 (2)	C21—C20—H20	119.9
C2—C3—H3	122.2	C19—C20—H20	119.9
N3—C3—H3	122.2	C22—C21—C20	120.7 (3)
N1—C4—C1	115.86 (18)	C22—C21—H21	119.7
N1—C4—C5	123.70 (19)	C20—C21—H21	119.7
C1—C4—C5	120.43 (18)	C23—C22—C21	120.2 (3)
C4—C5—H5A	109.5	C23—C22—H22	119.9
C4—C5—H5B	109.5	C21—C22—H22	119.9
H5A—C5—H5B	109.5	C22—C23—C24	120.2 (3)
C4—C5—H5C	109.5	C22—C23—H23	119.9
H5A—C5—H5C	109.5	C24—C23—H23	119.9
H5B—C5—H5C	109.5	C19—C24—C23	120.2 (3)
N2—C6—N4	118.77 (18)	C19—C24—H24	119.9
N2—C6—S1	127.81 (16)	C23—C24—H24	119.9
N4—C6—S1	113.42 (15)	C25—O1—H1S	107 (3)
C12—C7—C8	118.0 (2)	O1—C25—H25A	109.5
C12—C7—N4	116.7 (2)	O1—C25—H25B	109.5
C8—C7—N4	125.3 (2)	H25A—C25—H25B	109.5
C7—C8—C9	119.7 (3)	O1—C25—H25C	109.5
C7—C8—H8	120.1	H25A—C25—H25C	109.5
C9—C8—H8	120.1	H25B—C25—H25C	109.5
C10—C9—C8	122.2 (3)
C19—Sn1—S1—C6	−87.39 (9)	Sn1—S1—C6—N2	−0.3 (2)
C13—Sn1—S1—C6	92.81 (9)	Sn1—S1—C6—N4	179.95 (14)
N1—Sn1—S1—C6	−0.44 (8)	C6—N4—C7—C12	−173.6 (2)
N3—Sn1—S1—C6	2.17 (11)	C6—N4—C7—C8	7.1 (4)
Cl1—Sn1—S1—C6	−175.30 (7)	C12—C7—C8—C9	−0.3 (5)
C19—Sn1—N1—C4	−74.56 (18)	N4—C7—C8—C9	179.0 (3)
C13—Sn1—N1—C4	81.01 (17)	C7—C8—C9—C10	−0.5 (6)
S1—Sn1—N1—C4	−178.25 (17)	C8—C9—C10—C11	0.9 (6)
N3—Sn1—N1—C4	3.41 (16)	C9—C10—C11—C12	−0.4 (5)
Cl1—Sn1—N1—C4	−156.65 (15)	C8—C7—C12—C11	0.7 (4)
C19—Sn1—N1—N2	104.97 (15)	N4—C7—C12—C11	−178.6 (3)
C13—Sn1—N1—N2	−99.46 (15)	C10—C11—C12—C7	−0.4 (5)
S1—Sn1—N1—N2	1.28 (14)	C19—Sn1—C13—C18	−76.4 (3)
N3—Sn1—N1—N2	−177.06 (16)	N1—Sn1—C13—C18	−179.58 (19)
Cl1—Sn1—N1—N2	22.9 (3)	S1—Sn1—C13—C18	103.14 (19)
C4—N1—N2—C6	177.74 (19)	N3—Sn1—C13—C18	−113.5 (2)
Sn1—N1—N2—C6	−1.8 (2)	Cl1—Sn1—C13—C18	12.27 (19)
C19—Sn1—N3—C1	88.85 (16)	C19—Sn1—C13—C14	107.3 (2)
C13—Sn1—N3—C1	−106.27 (16)	N1—Sn1—C13—C14	4.12 (19)
N1—Sn1—N3—C1	−6.02 (14)	S1—Sn1—C13—C14	−73.16 (18)
S1—Sn1—N3—C1	−8.76 (19)	N3—Sn1—C13—C14	70.24 (18)
Cl1—Sn1—N3—C1	168.14 (13)	Cl1—Sn1—C13—C14	−164.03 (18)
C19—Sn1—N3—C3	−77.5 (2)	C18—C13—C14—C15	0.4 (4)
C13—Sn1—N3—C3	87.4 (2)	Sn1—C13—C14—C15	176.9 (2)
N1—Sn1—N3—C3	−172.3 (2)	C13—C14—C15—C16	−0.2 (5)
S1—Sn1—N3—C3	−175.08 (19)	C14—C15—C16—C17	−0.1 (5)
Cl1—Sn1—N3—C3	1.8 (2)	C15—C16—C17—C18	0.1 (5)
C3—N3—C1—C4	178.9 (2)	C14—C13—C18—C17	−0.4 (4)
Sn1—N3—C1—C4	8.7 (3)	Sn1—C13—C18—C17	−176.7 (2)
C3—N3—C1—S2	0.5 (2)	C16—C17—C18—C13	0.2 (5)
Sn1—N3—C1—S2	−169.73 (10)	C13—Sn1—C19—C24	−161.17 (19)
C2—S2—C1—N3	−0.6 (2)	N1—Sn1—C19—C24	−56.77 (17)
C2—S2—C1—C4	−179.0 (2)	S1—Sn1—C19—C24	19.30 (17)
C1—S2—C2—C3	0.5 (2)	N3—Sn1—C19—C24	−123.84 (17)
S2—C2—C3—N3	−0.3 (3)	Cl1—Sn1—C19—C24	109.30 (16)
C1—N3—C3—C2	−0.1 (3)	C13—Sn1—C19—C20	17.0 (3)
Sn1—N3—C3—C2	166.14 (19)	N1—Sn1—C19—C20	121.42 (17)
N2—N1—C4—C1	179.97 (17)	S1—Sn1—C19—C20	−162.51 (16)
Sn1—N1—C4—C1	−0.5 (3)	N3—Sn1—C19—C20	54.35 (16)
N2—N1—C4—C5	1.2 (3)	Cl1—Sn1—C19—C20	−72.51 (16)
Sn1—N1—C4—C5	−179.29 (18)	C24—C19—C20—C21	2.0 (3)
N3—C1—C4—N1	−6.4 (3)	Sn1—C19—C20—C21	−176.23 (17)
S2—C1—C4—N1	171.93 (17)	C19—C20—C21—C22	−0.9 (4)
N3—C1—C4—C5	172.5 (2)	C20—C21—C22—C23	−0.8 (4)
S2—C1—C4—C5	−9.2 (3)	C21—C22—C23—C24	1.4 (4)
N1—N2—C6—N4	−178.91 (18)	C20—C19—C24—C23	−1.4 (3)
N1—N2—C6—S1	1.4 (3)	Sn1—C19—C24—C23	176.88 (18)
C7—N4—C6—N2	4.4 (3)	C22—C23—C24—C19	−0.3 (4)
C7—N4—C6—S1	−175.87 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4N···O1	0.85 (2)	2.08 (2)	2.930 (3)	175 (2)
O1—H1S···Cl1i	0.76 (4)	2.52 (4)	3.248 (2)	162 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4N⋯O1	0.85 (2)	2.08 (2)	2.930 (3)	175 (2)
O1—H1S⋯Cl1i	0.76 (4)	2.52 (4)	3.248 (2)	162 (4)

Symmetry code: (i) .