Dichlorido[2,4-dimethyl-N-(pyridin-2-yl-methyl-idene)aniline-κN,N']dimethyl-tin(IV).

The asymmetric unit of the title compound, [Sn(CH(3))(2)Cl(2)(C(14)H(14)N(2))], contains two crystallographically independent mol-ecules. In each mol-ecule, the Sn(IV) atom is six-coordinated in a distorted octa-hedral geometry by one bidentate 2,4-di-methyl-N-(pyridin-2-yl-methyl-idene)aniline ligand, two methyl groups and two Cl atoms. In the crystal, inter-molecular C-H⋯Cl hydrogen bonds link the mol-ecules. There are π-π contacts between the pyridine rings of the ligands [centroid-centroid distance = 3.761 (4) Å].

Related literature

For applications of Schiff bases and their metal complexes, see: Azza & Abu (2006 ▶); Dudek & Dudek (1966 ▶); McAuliffe et al. (1986 ▶); Mladenova et al. (2002 ▶); Pandeya et al. (1999 ▶); Panneerselvam et al. (2005 ▶); Papić et al. (1994 ▶); Singh et al. (2006 ▶); Sridhar et al. (2001 ▶); Vlcek (2002 ▶); Walsh et al. (1996 ▶). For related structures, see: Ali et al. (2004 ▶); Fallah Nejad et al. (2010 ▶); Labisbal et al. (2006 ▶); Talei Bavil Olyai et al. (2008 ▶, 2010a ▶,b ▶).

Experimental

Crystal data

[Sn(CH3)2Cl2(C14H14N2)]

M = 429.95

Orthorhombic,

a = 15.507 (3) Å

b = 7.3500 (15) Å

c = 32.175 (6) Å

V = 3667.2 (12) Å3

Z = 8

Mo Kα radiation

μ = 1.68 mm−1

T = 298 K

0.30 × 0.28 × 0.20 mm

Data collection

Stoe IPDS-2 diffractometer

Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005 ▶) T min = 0.607, T max = 0.711

25085 measured reflections

9838 independent reflections

7280 reflections with I > 2σ(I)

R int = 0.080

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.116

S = 0.97

9838 reflections

387 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.75 e Å−3

Δρmin = −0.56 e Å−3

Absolute structure: Flack (1983 ▶), 4819 Friedel pairs

Flack parameter: 0.19 (3)

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811010439/hy2416sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010439/hy2416Isup2.hkl

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

[Sn(CH3)2Cl2(C14H14N2)]	F(000) = 1712.0
Mr = 429.95	Dx = 1.558 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 9838 reflections
a = 15.507 (3) Å	θ = 2.5–29.2°
b = 7.3500 (15) Å	µ = 1.68 mm−1
c = 32.175 (6) Å	T = 298 K
V = 3667.2 (12) Å3	Block, yellow
Z = 8	0.30 × 0.28 × 0.20 mm

Stoe IPDS-2 diffractometer	9838 independent reflections
Radiation source: fine-focus sealed tube	7280 reflections with I > 2σ(I)
graphite	Rint = 0.080
ω scans	θmax = 29.2°, θmin = 2.5°
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005)	h = −18→21
Tmin = 0.607, Tmax = 0.711	k = −10→9
25085 measured reflections	l = −44→44

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0637P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max = 0.004
9838 reflections	Δρmax = 0.75 e Å−3
387 parameters	Δρmin = −0.56 e Å−3
1 restraint	Absolute structure: Flack (1983), 4819 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.19 (3)

	x	y	z	Uiso*/Ueq
Sn1	0.18692 (2)	0.80347 (6)	0.431585 (9)	0.04196 (9)
N1	0.2970 (3)	0.9910 (7)	0.39634 (15)	0.0452 (11)
C10	0.3773 (4)	0.9827 (8)	0.41197 (18)	0.0448 (13)
C13	0.3446 (7)	1.2245 (11)	0.3505 (3)	0.056 (2)
H13	0.3318	1.3058	0.3292	0.067*
C4	0.3997 (5)	0.3521 (12)	0.5478 (3)	0.069 (2)
C11	0.4436 (4)	1.0900 (10)	0.3980 (2)	0.0545 (15)
H11	0.4988	1.0793	0.4091	0.065*
C7	0.2816 (7)	0.8040 (15)	0.5495 (3)	0.072 (2)
H7A	0.2225	0.7945	0.5408	0.107*
H7B	0.3064	0.9132	0.5384	0.107*
H7C	0.2840	0.8077	0.5793	0.107*
C6	0.3986 (5)	0.4761 (10)	0.4793 (2)	0.0574 (17)
H6	0.4134	0.4655	0.4514	0.069*
C1	0.3542 (4)	0.6262 (9)	0.49281 (18)	0.0467 (13)
C2	0.3302 (4)	0.6450 (10)	0.53432 (19)	0.0478 (14)
C3	0.3556 (5)	0.5078 (11)	0.5611 (2)	0.0574 (17)
H3	0.3428	0.5196	0.5892	0.069*
C12	0.4258 (6)	1.2161 (11)	0.3666 (3)	0.0568 (19)
H12	0.4688	1.2933	0.3568	0.068*
C14	0.2824 (4)	1.1118 (9)	0.36599 (18)	0.0484 (14)
H14	0.2271	1.1194	0.3549	0.058*
C5	0.4213 (5)	0.3404 (11)	0.5069 (3)	0.0646 (19)
H5	0.4519	0.2398	0.4974	0.078*
Sn2	1.06671 (2)	0.29828 (6)	0.226572 (9)	0.04186 (10)
N4	0.9250 (5)	0.2614 (8)	0.1941 (3)	0.0489 (17)
C22	0.8552 (5)	−0.0265 (11)	0.1770 (2)	0.0622 (19)
H22	0.8388	−0.0373	0.2047	0.075*
C29	0.9057 (8)	0.7210 (11)	0.3062 (3)	0.062 (2)
H29	0.9171	0.8027	0.3275	0.075*
C25	0.8622 (4)	0.3456 (9)	0.21111 (19)	0.0470 (14)
H25	0.8062	0.3227	0.2022	0.056*
C26	0.8770 (4)	0.4778 (9)	0.24446 (18)	0.0481 (14)
C17	0.9013 (4)	0.1215 (9)	0.16414 (18)	0.0452 (13)
C18	0.9281 (4)	0.1373 (9)	0.12304 (18)	0.0434 (12)
C21	0.8328 (5)	−0.1620 (11)	0.1484 (3)	0.068 (2)
H21	0.8007	−0.2620	0.1571	0.081*
C23	0.9785 (6)	0.2992 (12)	0.1078 (3)	0.0597 (17)
H23A	1.0367	0.2918	0.1178	0.090*
H23B	0.9522	0.4089	0.1179	0.090*
H23C	0.9787	0.3001	0.0779	0.090*
C19	0.9069 (4)	0.0013 (10)	0.09576 (19)	0.0524 (16)
H19	0.9259	0.0091	0.0684	0.063*
C28	0.8256 (6)	0.7091 (12)	0.2895 (3)	0.061 (2)
H28	0.7815	0.7838	0.2990	0.074*
C24	0.8344 (7)	−0.2936 (14)	0.0771 (4)	0.079 (3)
H24A	0.8789	−0.3031	0.0565	0.119*
H24B	0.7808	−0.2629	0.0639	0.119*
H24C	0.8285	−0.4078	0.0913	0.119*
C27	0.8106 (4)	0.5860 (11)	0.2585 (2)	0.0570 (16)
H27	0.7559	0.5754	0.2469	0.068*
C20	0.8578 (5)	−0.1481 (11)	0.1078 (2)	0.0584 (17)
C31	1.0238 (6)	0.0794 (11)	0.2644 (2)	0.068 (2)
H31A	0.9768	0.1196	0.2815	0.102*
H31B	1.0703	0.0386	0.2817	0.102*
H31C	1.0048	−0.0189	0.2470	0.102*
N2	0.3306 (5)	0.7655 (8)	0.4634 (2)	0.0436 (15)
N3	0.9570 (3)	0.4873 (7)	0.26072 (15)	0.0449 (11)
C32	1.0925 (5)	0.5382 (11)	0.1916 (2)	0.0621 (19)
H32A	1.0402	0.5801	0.1788	0.093*
H32B	1.1344	0.5116	0.1705	0.093*
H32C	1.1146	0.6308	0.2097	0.093*
C15	0.2288 (5)	0.5808 (12)	0.3946 (3)	0.067 (2)
H15A	0.2808	0.6136	0.3802	0.100*
H15B	0.1849	0.5508	0.3747	0.100*
H15C	0.2396	0.4776	0.4121	0.100*
Cl1	0.06818 (14)	0.8806 (4)	0.38104 (8)	0.0797 (6)
Cl2	0.11045 (12)	0.5992 (3)	0.48092 (6)	0.0696 (5)
C9	0.3909 (4)	0.8486 (10)	0.44574 (18)	0.0474 (14)
H9	0.4471	0.8249	0.4543	0.057*
Cl3	1.14422 (12)	0.0871 (3)	0.17892 (6)	0.0660 (5)
Cl4	1.18382 (14)	0.3783 (4)	0.27756 (8)	0.0805 (7)
C30	0.9704 (4)	0.6088 (10)	0.2907 (2)	0.0519 (15)
H30	1.0256	0.6192	0.3018	0.062*
C8	0.4216 (8)	0.2040 (17)	0.5793 (4)	0.104 (5)
H8A	0.3695	0.1456	0.5883	0.156*
H8B	0.4503	0.2573	0.6027	0.156*
H8C	0.4588	0.1156	0.5665	0.156*
C16	0.1653 (6)	1.0461 (11)	0.4656 (2)	0.068 (2)
H16A	0.2131	1.0675	0.4839	0.102*
H16B	0.1133	1.0343	0.4815	0.102*
H16C	0.1597	1.1464	0.4466	0.102*

	U11	U22	U33	U12	U13	U23
Sn1	0.03716 (19)	0.0435 (2)	0.0452 (2)	0.00291 (18)	−0.00340 (15)	0.0017 (3)
N1	0.049 (3)	0.044 (3)	0.043 (2)	0.004 (2)	0.002 (2)	0.005 (2)
C10	0.051 (3)	0.039 (3)	0.045 (3)	0.003 (3)	0.004 (3)	0.001 (2)
C13	0.073 (5)	0.046 (4)	0.048 (4)	0.005 (4)	0.004 (4)	0.005 (3)
C4	0.061 (4)	0.065 (5)	0.080 (5)	−0.021 (4)	−0.023 (4)	0.033 (4)
C11	0.045 (3)	0.062 (4)	0.056 (3)	−0.011 (3)	−0.004 (3)	0.004 (3)
C7	0.079 (6)	0.089 (6)	0.047 (4)	0.007 (5)	−0.001 (4)	−0.009 (5)
C6	0.049 (4)	0.064 (5)	0.059 (4)	0.012 (3)	0.006 (3)	0.009 (3)
C1	0.047 (3)	0.047 (3)	0.046 (3)	0.005 (3)	−0.008 (2)	0.010 (3)
C2	0.040 (3)	0.055 (3)	0.048 (3)	−0.007 (3)	−0.007 (3)	0.005 (3)
C3	0.050 (4)	0.071 (5)	0.051 (3)	−0.014 (3)	−0.016 (3)	0.019 (3)
C12	0.066 (5)	0.051 (4)	0.053 (4)	−0.014 (4)	0.004 (4)	0.007 (3)
C14	0.050 (3)	0.045 (4)	0.050 (3)	0.009 (3)	−0.006 (3)	0.007 (3)
C5	0.045 (4)	0.056 (4)	0.093 (5)	0.009 (3)	0.004 (4)	0.016 (4)
Sn2	0.0385 (2)	0.0460 (2)	0.04104 (19)	−0.00384 (18)	−0.00327 (16)	0.0047 (3)
N4	0.059 (4)	0.046 (3)	0.042 (4)	−0.006 (2)	0.003 (3)	−0.002 (2)
C22	0.056 (4)	0.071 (5)	0.060 (4)	−0.022 (4)	0.011 (3)	−0.005 (3)
C29	0.099 (6)	0.036 (3)	0.052 (4)	−0.011 (4)	0.004 (4)	−0.006 (3)
C25	0.032 (3)	0.055 (4)	0.054 (3)	−0.003 (3)	−0.005 (2)	−0.006 (3)
C26	0.054 (4)	0.048 (4)	0.043 (3)	−0.003 (3)	0.003 (3)	−0.001 (3)
C17	0.041 (3)	0.046 (3)	0.049 (3)	−0.002 (3)	−0.010 (3)	−0.006 (3)
C18	0.035 (3)	0.051 (3)	0.044 (3)	0.001 (3)	−0.003 (2)	0.003 (2)
C21	0.061 (4)	0.060 (5)	0.083 (5)	−0.023 (4)	0.003 (4)	−0.008 (4)
C23	0.068 (5)	0.059 (4)	0.052 (4)	0.001 (4)	0.004 (3)	0.014 (4)
C19	0.040 (3)	0.068 (5)	0.049 (3)	0.008 (3)	−0.007 (2)	−0.009 (3)
C28	0.073 (5)	0.051 (4)	0.061 (4)	0.009 (5)	0.009 (4)	−0.005 (4)
C24	0.064 (5)	0.080 (6)	0.093 (7)	−0.001 (5)	−0.028 (5)	−0.028 (6)
C27	0.043 (3)	0.069 (5)	0.060 (4)	0.000 (3)	−0.002 (3)	−0.003 (3)
C20	0.049 (4)	0.052 (4)	0.075 (4)	0.001 (3)	−0.014 (3)	−0.012 (3)
C31	0.081 (5)	0.057 (4)	0.066 (4)	−0.006 (4)	0.019 (4)	0.022 (4)
N2	0.047 (3)	0.044 (3)	0.040 (4)	0.003 (2)	−0.004 (3)	0.006 (2)
N3	0.050 (3)	0.044 (3)	0.040 (2)	−0.003 (2)	0.000 (2)	−0.002 (2)
C32	0.056 (4)	0.058 (4)	0.072 (4)	−0.010 (4)	0.003 (4)	0.016 (4)
C15	0.067 (5)	0.056 (5)	0.078 (5)	0.004 (4)	0.008 (4)	−0.014 (4)
Cl1	0.0749 (14)	0.0828 (16)	0.0814 (13)	0.0083 (11)	−0.0377 (11)	0.0094 (12)
Cl2	0.0537 (10)	0.0867 (14)	0.0685 (10)	−0.0146 (10)	−0.0044 (8)	0.0259 (10)
C9	0.033 (3)	0.060 (4)	0.049 (3)	0.003 (3)	−0.011 (2)	0.008 (3)
Cl3	0.0560 (10)	0.0825 (14)	0.0594 (9)	0.0141 (9)	−0.0025 (8)	−0.0122 (9)
Cl4	0.0789 (15)	0.0832 (17)	0.0793 (13)	−0.0066 (11)	−0.0410 (10)	−0.0038 (12)
C30	0.050 (3)	0.052 (4)	0.054 (3)	−0.007 (3)	−0.005 (3)	0.004 (3)
C8	0.084 (7)	0.100 (8)	0.129 (10)	−0.022 (7)	−0.043 (7)	0.072 (8)
C16	0.079 (5)	0.058 (5)	0.066 (4)	0.019 (4)	0.000 (4)	−0.011 (4)

Sn1—C15	2.126 (8)	C29—C28	1.355 (14)
Sn1—C16	2.118 (7)	C29—C30	1.391 (12)
Sn1—N1	2.470 (5)	C29—H29	0.9300
Sn1—N2	2.468 (8)	C25—C26	1.466 (9)
Sn1—Cl1	2.5213 (19)	C25—H25	0.9300
Sn1—Cl2	2.4859 (19)	C26—N3	1.348 (8)
N1—C14	1.339 (8)	C26—C27	1.377 (9)
N1—C10	1.345 (8)	C17—C18	1.391 (9)
C10—C11	1.371 (9)	C18—C19	1.371 (9)
C10—C9	1.482 (8)	C18—C23	1.505 (10)
C13—C12	1.363 (14)	C21—C20	1.367 (11)
C13—C14	1.367 (12)	C21—H21	0.9300
C13—H13	0.9300	C23—H23A	0.9600
C4—C5	1.361 (12)	C23—H23B	0.9600
C4—C3	1.401 (12)	C23—H23C	0.9600
C4—C8	1.525 (11)	C19—C20	1.390 (11)
C11—C12	1.400 (11)	C19—H19	0.9300
C11—H11	0.9300	C28—C27	1.368 (11)
C7—C2	1.475 (12)	C28—H28	0.9300
C7—H7A	0.9600	C24—C20	1.500 (11)
C7—H7B	0.9600	C24—H24A	0.9600
C7—H7C	0.9600	C24—H24B	0.9600
C6—C1	1.371 (10)	C24—H24C	0.9600
C6—C5	1.382 (10)	C27—H27	0.9300
C6—H6	0.9300	C31—H31A	0.9600
C1—C2	1.393 (9)	C31—H31B	0.9600
C1—N2	1.441 (9)	C31—H31C	0.9600
C2—C3	1.384 (9)	N2—C9	1.254 (10)
C3—H3	0.9300	N3—C30	1.332 (8)
C12—H12	0.9300	C32—H32A	0.9600
C14—H14	0.9300	C32—H32B	0.9600
C5—H5	0.9300	C32—H32C	0.9600
Sn2—C31	2.124 (7)	C15—H15A	0.9600
Sn2—C32	2.130 (7)	C15—H15B	0.9600
Sn2—N3	2.456 (5)	C15—H15C	0.9600
Sn2—N4	2.449 (8)	C9—H9	0.9300
Sn2—Cl3	2.4908 (19)	C30—H30	0.9300
Sn2—Cl4	2.5170 (19)	C8—H8A	0.9600
N4—C25	1.277 (10)	C8—H8B	0.9600
N4—C17	1.456 (9)	C8—H8C	0.9600
C22—C17	1.365 (10)	C16—H16A	0.9600
C22—C21	1.399 (10)	C16—H16B	0.9600
C22—H22	0.9300	C16—H16C	0.9600
C16—Sn1—C15	170.2 (4)	N4—C25—C26	121.0 (6)
C16—Sn1—N2	91.4 (3)	N4—C25—H25	119.5
C15—Sn1—N2	82.5 (3)	C26—C25—H25	119.5
C16—Sn1—N1	82.9 (3)	N3—C26—C27	122.1 (6)
C15—Sn1—N1	87.8 (3)	N3—C26—C25	117.6 (5)
N2—Sn1—N1	68.3 (2)	C27—C26—C25	120.3 (6)
C16—Sn1—Cl2	95.9 (3)	C22—C17—C18	120.7 (6)
C15—Sn1—Cl2	92.2 (2)	C22—C17—N4	119.6 (6)
N2—Sn1—Cl2	95.58 (17)	C18—C17—N4	119.6 (6)
N1—Sn1—Cl2	163.73 (13)	C19—C18—C17	118.4 (6)
C16—Sn1—Cl1	91.6 (2)	C19—C18—C23	119.5 (6)
C15—Sn1—Cl1	92.0 (2)	C17—C18—C23	122.1 (6)
N2—Sn1—Cl1	162.27 (19)	C20—C21—C22	120.3 (7)
N1—Sn1—Cl1	94.76 (13)	C20—C21—H21	119.9
Cl2—Sn1—Cl1	101.49 (8)	C22—C21—H21	119.9
C14—N1—C10	117.3 (5)	C18—C23—H23A	109.5
C14—N1—Sn1	126.0 (4)	C18—C23—H23B	109.5
C10—N1—Sn1	116.3 (4)	H23A—C23—H23B	109.5
N1—C10—C11	123.1 (6)	C18—C23—H23C	109.5
N1—C10—C9	115.8 (5)	H23A—C23—H23C	109.5
C11—C10—C9	121.1 (6)	H23B—C23—H23C	109.5
C12—C13—C14	119.1 (8)	C18—C19—C20	122.0 (6)
C12—C13—H13	120.5	C18—C19—H19	119.0
C14—C13—H13	120.5	C20—C19—H19	119.0
C5—C4—C3	117.9 (7)	C29—C28—C27	119.2 (8)
C5—C4—C8	122.8 (10)	C29—C28—H28	120.4
C3—C4—C8	119.3 (9)	C27—C28—H28	120.4
C10—C11—C12	118.0 (7)	C20—C24—H24A	109.5
C10—C11—H11	121.0	C20—C24—H24B	109.5
C12—C11—H11	121.0	H24A—C24—H24B	109.5
C2—C7—H7A	109.5	C20—C24—H24C	109.5
C2—C7—H7B	109.5	H24A—C24—H24C	109.5
H7A—C7—H7B	109.5	H24B—C24—H24C	109.5
C2—C7—H7C	109.5	C28—C27—C26	119.6 (7)
H7A—C7—H7C	109.5	C28—C27—H27	120.2
H7B—C7—H7C	109.5	C26—C27—H27	120.2
C1—C6—C5	120.3 (7)	C21—C20—C19	118.7 (7)
C1—C6—H6	119.9	C21—C20—C24	120.5 (8)
C5—C6—H6	119.9	C19—C20—C24	120.8 (8)
C6—C1—C2	121.2 (6)	Sn2—C31—H31A	109.5
C6—C1—N2	119.4 (6)	Sn2—C31—H31B	109.5
C2—C1—N2	119.4 (6)	H31A—C31—H31B	109.5
C3—C2—C1	116.7 (7)	Sn2—C31—H31C	109.5
C3—C2—C7	121.1 (7)	H31A—C31—H31C	109.5
C1—C2—C7	122.2 (6)	H31B—C31—H31C	109.5
C2—C3—C4	122.9 (7)	C9—N2—C1	117.1 (7)
C2—C3—H3	118.5	C9—N2—Sn1	115.4 (5)
C4—C3—H3	118.5	C1—N2—Sn1	125.6 (5)
C13—C12—C11	119.2 (8)	C30—N3—C26	117.4 (6)
C13—C12—H12	120.4	C30—N3—Sn2	126.5 (4)
C11—C12—H12	120.4	C26—N3—Sn2	115.8 (4)
N1—C14—C13	123.3 (7)	Sn2—C32—H32A	109.5
N1—C14—H14	118.3	Sn2—C32—H32B	109.5
C13—C14—H14	118.3	H32A—C32—H32B	109.5
C4—C5—C6	120.9 (8)	Sn2—C32—H32C	109.5
C4—C5—H5	119.5	H32A—C32—H32C	109.5
C6—C5—H5	119.5	H32B—C32—H32C	109.5
C31—Sn2—C32	171.4 (3)	Sn1—C15—H15A	109.5
C31—Sn2—N4	83.1 (3)	Sn1—C15—H15B	109.5
C32—Sn2—N4	92.0 (3)	H15A—C15—H15B	109.5
C31—Sn2—N3	87.4 (3)	Sn1—C15—H15C	109.5
C32—Sn2—N3	84.2 (3)	H15A—C15—H15C	109.5
N4—Sn2—N3	68.4 (2)	H15B—C15—H15C	109.5
C31—Sn2—Cl3	91.8 (2)	N2—C9—C10	123.4 (6)
C32—Sn2—Cl3	95.7 (2)	N2—C9—H9	118.3
N4—Sn2—Cl3	95.82 (18)	C10—C9—H9	118.3
N3—Sn2—Cl3	164.18 (12)	N3—C30—C29	122.9 (7)
C31—Sn2—Cl4	91.7 (3)	N3—C30—H30	118.5
C32—Sn2—Cl4	90.9 (2)	C29—C30—H30	118.5
N4—Sn2—Cl4	162.1 (2)	C4—C8—H8A	109.5
N3—Sn2—Cl4	94.36 (13)	C4—C8—H8B	109.5
Cl3—Sn2—Cl4	101.46 (8)	H8A—C8—H8B	109.5
C25—N4—C17	115.7 (7)	C4—C8—H8C	109.5
C25—N4—Sn2	116.6 (5)	H8A—C8—H8C	109.5
C17—N4—Sn2	125.9 (5)	H8B—C8—H8C	109.5
C17—C22—C21	119.9 (7)	Sn1—C16—H16A	109.5
C17—C22—H22	120.1	Sn1—C16—H16B	109.5
C21—C22—H22	120.1	H16A—C16—H16B	109.5
C28—C29—C30	118.8 (8)	Sn1—C16—H16C	109.5
C28—C29—H29	120.6	H16A—C16—H16C	109.5
C30—C29—H29	120.6	H16B—C16—H16C	109.5
C16—Sn1—N1—C14	−80.3 (6)	C25—N4—C17—C18	119.1 (8)
C15—Sn1—N1—C14	102.6 (5)	Sn2—N4—C17—C18	−76.7 (8)
N2—Sn1—N1—C14	−174.6 (6)	C22—C17—C18—C19	0.3 (10)
Cl2—Sn1—N1—C14	−167.1 (4)	N4—C17—C18—C19	178.3 (6)
Cl1—Sn1—N1—C14	10.8 (5)	C22—C17—C18—C23	179.6 (7)
C16—Sn1—N1—C10	93.0 (5)	N4—C17—C18—C23	−2.4 (10)
C15—Sn1—N1—C10	−84.1 (5)	C17—C22—C21—C20	0.9 (13)
N2—Sn1—N1—C10	−1.3 (4)	C17—C18—C19—C20	1.7 (9)
Cl2—Sn1—N1—C10	6.1 (8)	C23—C18—C19—C20	−177.6 (7)
Cl1—Sn1—N1—C10	−176.0 (4)	C30—C29—C28—C27	0.8 (13)
C14—N1—C10—C11	−0.6 (9)	C29—C28—C27—C26	−0.6 (12)
Sn1—N1—C10—C11	−174.4 (5)	N3—C26—C27—C28	0.8 (11)
C14—N1—C10—C9	179.5 (5)	C25—C26—C27—C28	−179.7 (7)
Sn1—N1—C10—C9	5.6 (7)	C22—C21—C20—C19	1.0 (12)
N1—C10—C11—C12	1.3 (10)	C22—C21—C20—C24	179.6 (8)
C9—C10—C11—C12	−178.8 (7)	C18—C19—C20—C21	−2.4 (11)
C5—C6—C1—C2	−0.7 (11)	C18—C19—C20—C24	179.1 (7)
C5—C6—C1—N2	−179.6 (7)	C6—C1—N2—C9	−63.2 (10)
C6—C1—C2—C3	1.8 (10)	C2—C1—N2—C9	117.8 (8)
N2—C1—C2—C3	−179.3 (6)	C6—C1—N2—Sn1	100.3 (7)
C6—C1—C2—C7	−179.2 (8)	C2—C1—N2—Sn1	−78.7 (8)
N2—C1—C2—C7	−0.3 (11)	C16—Sn1—N2—C9	−85.7 (6)
C1—C2—C3—C4	−2.9 (10)	C15—Sn1—N2—C9	86.7 (6)
C7—C2—C3—C4	178.1 (8)	N1—Sn1—N2—C9	−3.9 (5)
C5—C4—C3—C2	2.8 (11)	Cl2—Sn1—N2—C9	178.2 (6)
C8—C4—C3—C2	−177.3 (8)	Cl1—Sn1—N2—C9	13.9 (10)
C14—C13—C12—C11	1.2 (13)	C16—Sn1—N2—C1	110.6 (6)
C10—C11—C12—C13	−1.6 (12)	C15—Sn1—N2—C1	−77.0 (6)
C10—N1—C14—C13	0.2 (10)	N1—Sn1—N2—C1	−167.6 (7)
Sn1—N1—C14—C13	173.4 (6)	Cl2—Sn1—N2—C1	14.5 (6)
C12—C13—C14—N1	−0.5 (12)	Cl1—Sn1—N2—C1	−149.8 (5)
C3—C4—C5—C6	−1.6 (12)	C27—C26—N3—C30	−1.2 (9)
C8—C4—C5—C6	178.6 (8)	C25—C26—N3—C30	179.3 (5)
C1—C6—C5—C4	0.6 (12)	C27—C26—N3—Sn2	−175.2 (5)
C31—Sn2—N4—C25	85.9 (6)	C25—C26—N3—Sn2	5.4 (7)
C32—Sn2—N4—C25	−87.0 (6)	C31—Sn2—N3—C30	102.2 (5)
N3—Sn2—N4—C25	−4.1 (5)	C32—Sn2—N3—C30	−79.8 (5)
Cl3—Sn2—N4—C25	177.0 (6)	N4—Sn2—N3—C30	−174.3 (6)
Cl4—Sn2—N4—C25	12.1 (10)	Cl3—Sn2—N3—C30	−170.2 (4)
C31—Sn2—N4—C17	−78.2 (6)	Cl4—Sn2—N3—C30	10.6 (5)
C32—Sn2—N4—C17	108.9 (6)	C31—Sn2—N3—C26	−84.5 (5)
N3—Sn2—N4—C17	−168.2 (7)	C32—Sn2—N3—C26	93.5 (5)
Cl3—Sn2—N4—C17	12.9 (6)	N4—Sn2—N3—C26	−1.0 (4)
Cl4—Sn2—N4—C17	−152.0 (5)	Cl3—Sn2—N3—C26	3.1 (8)
C17—N4—C25—C26	174.4 (6)	Cl4—Sn2—N3—C26	−176.1 (4)
Sn2—N4—C25—C26	8.7 (9)	C1—N2—C9—C10	174.0 (6)
N4—C25—C26—N3	−9.7 (10)	Sn1—N2—C9—C10	8.8 (9)
N4—C25—C26—C27	170.8 (7)	N1—C10—C9—N2	−10.1 (10)
C21—C22—C17—C18	−1.6 (11)	C11—C10—C9—N2	169.9 (7)
C21—C22—C17—N4	−179.6 (7)	C26—N3—C30—C29	1.5 (10)
C25—N4—C17—C22	−62.9 (10)	Sn2—N3—C30—C29	174.7 (5)
Sn2—N4—C17—C22	101.3 (8)	C28—C29—C30—N3	−1.3 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cl2i	0.93	2.73	3.608 (6)	157
C25—H25···Cl3ii	0.93	2.70	3.570 (7)	155

Table 1

Selected bond lengths (Å)

Sn1—C15	2.126 (8)
Sn1—C16	2.118 (7)
Sn1—N1	2.470 (5)
Sn1—N2	2.468 (8)
Sn1—Cl1	2.5213 (19)
Sn1—Cl2	2.4859 (19)
Sn2—C31	2.124 (7)
Sn2—C32	2.130 (7)
Sn2—N3	2.456 (5)
Sn2—N4	2.449 (8)
Sn2—Cl3	2.4908 (19)
Sn2—Cl4	2.5170 (19)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯Cl2i	0.93	2.73	3.608 (6)	157
C25—H25⋯Cl3ii	0.93	2.70	3.570 (7)	155

Symmetry codes: (i) ; (ii) .