Bis(tetra-phenyl-phospho-nium) tris-[N-(methyl-sulfon-yl)dithio-carbimato(2-)-κS,S']stannate(IV).

In the title complex, (C(24)H(20)P)(2)[Sn(C(2)H(3)NO(2)S(3))(3)], the Sn(IV) atom is coordinated by three N-(methyl-sulfon-yl)dithio-carbimate bidentate ligands through the anionic S atoms in a slightly distorted octa-hedral coordination geometry. There is one half-mol-ecule in the asymmetric unit; the complex is located on a crystallographic twofold rotation axis passing through the cation and bis-ecting one of the (non-symmetric) ligands, which appears thus disordered over two sites of equal occupancy. In the crystal structure, weak inter-molecular C-H⋯O and C-H⋯S inter-actions contribute to the packing stabilization.

Related literature

For general background to tin(IV) dithio­carbamates, see: Barone et al. (2002 ▶); Coucouvanis (1979 ▶); Heard (2005 ▶); Menezes et al. (2005 ▶); Seth et al. (1992 ▶). For related structures of transition n class="Chemical">metal (Ni, Pt and Zn) complexes with dithio­carbimates derived from sulfonamides, see: Alves et al. (2009 ▶); Amim et al. (2008 ▶); Franca et al. (2006 ▶); Menezes et al. (2005 ▶). For the ligand synthesis, see: Hartke (1966 ▶).

Experimental

Crystal data

(C24H20P)2[Sn(C2H3NO2S3)3]

M = 1305.13

Monoclinic,

a = 18.5563 (3) Å

b = 13.6096 (2) Å

c = 23.3203 (3) Å

β = 91.355 (1)°

V = 5887.75 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.86 mm−1

T = 298 K

0.40 × 0.11 × 0.07 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: gaussian (n class="Chemical">Coppens et al., 1965 ▶) T min = 0.726, T max = 0.943

17695 measured reflections

5178 independent reflections

4871 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.138

S = 1.25

5178 reflections

372 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.80 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; 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 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034114/bg2277sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034114/bg2277Isup2.hkl

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

(C24H20P)2[Sn(C2H3NO2S3)3]	F(000) = 2664
Mr = 1305.13	Dx = 1.472 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 37024 reflections
a = 18.5563 (3) Å	θ = 2.9–26.4°
b = 13.6096 (2) Å	µ = 0.86 mm−1
c = 23.3203 (3) Å	T = 298 K
β = 91.355 (1)°	Prism, colourless
V = 5887.75 (15) Å3	0.40 × 0.11 × 0.07 mm
Z = 4

Nonius KappaCCD diffractometer	4871 reflections with I > 2σ(I)
CCD rotation images, thick slices scans	Rint = 0.049
Absorption correction: gaussian (Coppens et al., 1965)	θmax = 25.0°, θmin = 3.2°
Tmin = 0.726, Tmax = 0.943	h = −22→22
17695 measured reflections	k = −16→15
5178 independent reflections	l = −27→27

Refinement on F2	1 restraint
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.068	w = 1/[σ2(Fo2) + (0.0524P)2 + 7.2513P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.138	(Δ/σ)max < 0.001
S = 1.25	Δρmax = 0.62 e Å−3
5178 reflections	Δρmin = −0.80 e Å−3
372 parameters

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.1377 (2)	0.3823 (4)	0.23827 (19)	0.0512 (11)
C2	0.3047 (4)	0.2250 (6)	0.2112 (3)	0.097 (2)
H2A	0.2987	0.1898	0.2464	0.146*
H2B	0.3355	0.2807	0.218	0.146*
H2C	0.3261	0.1825	0.1835	0.146*
C3	0.0123 (6)	0.7091 (10)	0.2265 (5)	0.054 (3)	0.5
C4	0.0208 (8)	0.9908 (8)	0.2192 (6)	0.084 (4)	0.5
H4A	0	1.0435	0.25	0.126*
H4B	0.0692	0.9963	0.2088	0.126*	0.5
H4C	−0.01	0.9968	0.1853	0.126*	0.5
C5	0.1135 (3)	0.1693 (4)	0.42704 (19)	0.0513 (11)
C6	0.1645 (3)	0.0950 (4)	0.4278 (2)	0.0630 (13)
H6	0.1825	0.071	0.4626	0.076*
C7	0.1888 (4)	0.0563 (4)	0.3767 (3)	0.0807 (17)
H7	0.2227	0.006	0.3773	0.097*
C8	0.1626 (4)	0.0925 (5)	0.3254 (3)	0.0826 (19)
H8	0.1788	0.0661	0.2912	0.099*
C9	0.1128 (3)	0.1669 (5)	0.3238 (2)	0.0737 (16)
H9	0.0957	0.1912	0.2888	0.088*
C10	0.0883 (3)	0.2056 (4)	0.3743 (2)	0.0602 (13)
H10	0.0546	0.2563	0.3733	0.072*
C11	−0.0120 (2)	0.1986 (3)	0.50305 (17)	0.0482 (11)
C12	−0.0622 (3)	0.1985 (4)	0.45823 (19)	0.0546 (12)
H12	−0.0472	0.207	0.4208	0.065*
C13	−0.1347 (3)	0.1858 (4)	0.4689 (2)	0.0617 (13)
H13	−0.1682	0.1852	0.4386	0.074*
C14	−0.1570 (3)	0.1742 (4)	0.5237 (2)	0.0656 (14)
H14	−0.2057	0.1654	0.5307	0.079*
C15	−0.1080 (3)	0.1753 (4)	0.5685 (2)	0.0715 (15)
H15	−0.1237	0.1677	0.6058	0.086*
C16	−0.0362 (3)	0.1877 (4)	0.5588 (2)	0.0654 (14)
H16	−0.0034	0.1887	0.5896	0.079*
C17	0.1296 (2)	0.1673 (4)	0.55250 (18)	0.0492 (11)
C18	0.1161 (3)	0.0707 (4)	0.5669 (2)	0.0622 (13)
H18	0.0847	0.0335	0.5441	0.075*
C19	0.1486 (3)	0.0285 (4)	0.6148 (2)	0.0689 (14)
H19	0.1392	−0.0366	0.6243	0.083*
C20	0.1953 (3)	0.0845 (5)	0.6485 (2)	0.0722 (16)
H20	0.2174	0.0568	0.6809	0.087*
C21	0.2091 (3)	0.1798 (5)	0.6346 (2)	0.0731 (17)
H21	0.2405	0.2167	0.6577	0.088*
C22	0.1768 (3)	0.2223 (4)	0.5866 (2)	0.0622 (13)
H22	0.1868	0.2873	0.5772	0.075*
C23	0.0993 (3)	0.3510 (4)	0.4934 (2)	0.0541 (12)
C24	0.1468 (3)	0.3929 (4)	0.4560 (3)	0.0711 (15)
H24	0.1673	0.355	0.4275	0.085*
C25	0.1640 (4)	0.4919 (4)	0.4611 (3)	0.092 (2)
H25	0.1957	0.5206	0.4356	0.11*
C26	0.1348 (4)	0.5465 (5)	0.5030 (4)	0.102 (2)
H26	0.1471	0.6125	0.5067	0.122*
C27	0.0883 (5)	0.5062 (5)	0.5395 (4)	0.114 (3)
H27	0.0688	0.5445	0.5683	0.137*
C28	0.0690 (4)	0.4077 (5)	0.5346 (3)	0.093 (2)
H28	0.0356	0.3808	0.5592	0.111*
N1	0.1997 (2)	0.3395 (3)	0.23680 (16)	0.0549 (10)
N3	0.0164 (4)	0.8014 (7)	0.2123 (3)	0.059 (2)	0.5
O1	0.1729 (2)	0.1825 (3)	0.18192 (17)	0.0874 (13)
O2	0.2311 (2)	0.3177 (3)	0.13255 (15)	0.0814 (12)
O3	−0.0270 (8)	0.8837 (7)	0.1904 (4)	0.134 (5)	0.5
O4	−0.0792 (5)	0.8933 (8)	0.2542 (6)	0.132 (4)	0.5
P1	0.08248 (6)	0.22110 (9)	0.49273 (5)	0.0472 (3)
S1	0.12124 (7)	0.45967 (11)	0.29633 (6)	0.0639 (4)
S2	0.06587 (7)	0.37025 (12)	0.18873 (5)	0.0676 (4)
S3	0.22079 (7)	0.26505 (11)	0.18510 (5)	0.0629 (4)
S5	0.01886 (19)	0.6562 (3)	0.21037 (15)	0.0599 (8)	0.5
S4	0.04165 (16)	0.6248 (2)	0.17458 (13)	0.0629 (7)	0.5
S6	0	0.88818 (17)	0.25	0.0880 (7)
Sn1	0	0.49240 (4)	0.25	0.0642 (2)

	U11	U22	U33	U12	U13	U23
C1	0.053 (3)	0.053 (3)	0.047 (2)	−0.009 (2)	−0.010 (2)	0.005 (2)
C2	0.091 (4)	0.108 (5)	0.092 (5)	0.040 (4)	−0.011 (4)	−0.022 (4)
C3	0.041 (6)	0.061 (9)	0.060 (7)	−0.007 (6)	0.001 (5)	0.002 (6)
C4	0.109 (10)	0.043 (7)	0.099 (9)	0.013 (6)	0.004 (7)	0.007 (6)
C5	0.059 (3)	0.047 (3)	0.047 (3)	−0.009 (2)	0.002 (2)	−0.002 (2)
C6	0.075 (3)	0.056 (3)	0.059 (3)	0.008 (3)	0.009 (2)	−0.001 (2)
C7	0.103 (5)	0.056 (4)	0.085 (4)	0.004 (3)	0.028 (4)	−0.012 (3)
C8	0.115 (5)	0.071 (4)	0.062 (4)	−0.029 (4)	0.026 (3)	−0.023 (3)
C9	0.095 (4)	0.076 (4)	0.050 (3)	−0.026 (4)	0.002 (3)	−0.003 (3)
C10	0.071 (3)	0.061 (3)	0.048 (3)	−0.009 (3)	0.002 (2)	−0.001 (2)
C11	0.056 (3)	0.047 (3)	0.041 (2)	−0.003 (2)	−0.003 (2)	−0.0003 (19)
C12	0.064 (3)	0.057 (3)	0.042 (2)	0.001 (2)	−0.008 (2)	0.000 (2)
C13	0.057 (3)	0.063 (3)	0.064 (3)	0.001 (2)	−0.017 (2)	−0.001 (3)
C14	0.051 (3)	0.066 (4)	0.080 (4)	−0.004 (3)	0.001 (3)	0.007 (3)
C15	0.064 (3)	0.090 (4)	0.061 (3)	−0.003 (3)	0.006 (3)	0.012 (3)
C16	0.057 (3)	0.089 (4)	0.049 (3)	−0.005 (3)	−0.008 (2)	0.006 (3)
C17	0.047 (2)	0.059 (3)	0.041 (2)	0.000 (2)	−0.0049 (19)	−0.004 (2)
C18	0.070 (3)	0.060 (4)	0.055 (3)	0.002 (3)	−0.015 (2)	−0.003 (2)
C19	0.075 (4)	0.070 (4)	0.061 (3)	0.013 (3)	−0.009 (3)	0.009 (3)
C20	0.058 (3)	0.106 (5)	0.051 (3)	0.019 (3)	−0.010 (2)	0.005 (3)
C21	0.055 (3)	0.115 (6)	0.049 (3)	−0.008 (3)	−0.011 (2)	−0.007 (3)
C22	0.058 (3)	0.077 (4)	0.051 (3)	−0.008 (3)	−0.003 (2)	−0.002 (3)
C23	0.060 (3)	0.045 (3)	0.057 (3)	−0.002 (2)	0.002 (2)	−0.009 (2)
C24	0.075 (4)	0.051 (3)	0.087 (4)	−0.004 (3)	0.014 (3)	−0.009 (3)
C25	0.096 (5)	0.056 (4)	0.125 (6)	−0.016 (3)	0.028 (4)	−0.008 (4)
C26	0.108 (5)	0.054 (4)	0.143 (7)	−0.012 (4)	0.016 (5)	−0.017 (4)
C27	0.154 (7)	0.066 (5)	0.126 (6)	−0.003 (5)	0.041 (6)	−0.044 (4)
C28	0.119 (5)	0.067 (4)	0.094 (4)	−0.008 (4)	0.042 (4)	−0.026 (4)
N1	0.052 (2)	0.060 (3)	0.052 (2)	0.001 (2)	−0.0102 (17)	−0.0085 (19)
N3	0.066 (5)	0.058 (6)	0.054 (5)	0.002 (4)	0.007 (4)	−0.012 (4)
O1	0.110 (3)	0.079 (3)	0.074 (3)	−0.031 (2)	0.014 (2)	−0.023 (2)
O2	0.080 (3)	0.110 (3)	0.055 (2)	−0.010 (2)	0.0100 (18)	0.006 (2)
O3	0.270 (15)	0.073 (6)	0.058 (5)	−0.038 (8)	−0.046 (7)	0.013 (4)
O4	0.095 (7)	0.110 (8)	0.193 (12)	−0.006 (6)	0.054 (7)	−0.038 (8)
P1	0.0522 (7)	0.0475 (7)	0.0416 (6)	−0.0017 (5)	−0.0034 (5)	−0.0020 (5)
S1	0.0551 (7)	0.0641 (9)	0.0713 (8)	0.0058 (6)	−0.0250 (6)	−0.0177 (7)
S2	0.0568 (7)	0.0928 (11)	0.0523 (7)	−0.0070 (7)	−0.0166 (6)	−0.0055 (7)
S3	0.0668 (8)	0.0698 (9)	0.0521 (7)	−0.0048 (7)	−0.0010 (6)	−0.0083 (6)
S5	0.0665 (19)	0.060 (2)	0.053 (2)	−0.0027 (18)	0.0020 (15)	0.0058 (16)
S4	0.0832 (19)	0.0563 (17)	0.0500 (15)	−0.0006 (14)	0.0157 (14)	−0.0023 (13)
S6	0.112 (2)	0.0629 (14)	0.0878 (16)	0	−0.0187 (13)	0
Sn1	0.0555 (3)	0.0525 (4)	0.0834 (4)	0	−0.0268 (3)	0

C1—N1	1.290 (6)	C17—P1	1.785 (4)
C1—S1	1.748 (5)	C18—C19	1.381 (7)
C1—S2	1.751 (4)	C18—H18	0.93
C2—S3	1.746 (6)	C19—C20	1.385 (8)
C2—H2A	0.96	C19—H19	0.93
C2—H2B	0.96	C20—C21	1.363 (8)
C2—H2C	0.96	C20—H20	0.93
C3—S5	0.822 (12)	C21—C22	1.385 (7)
C3—N3	1.302 (15)	C21—H21	0.93
C3—S5i	1.750 (12)	C22—H22	0.93
C3—S4	1.763 (14)	C23—C28	1.364 (7)
C4—S6	1.621 (11)	C23—C24	1.378 (7)
C4—O4i	1.813 (16)	C23—P1	1.795 (5)
C4—O3	1.826 (16)	C24—C25	1.389 (8)
C4—H4A	1.0919	C24—H24	0.93
C4—H4B	0.9393	C25—C26	1.352 (9)
C4—H4C	0.9675	C25—H25	0.93
C5—C6	1.383 (7)	C26—C27	1.343 (10)
C5—C10	1.396 (7)	C26—H26	0.93
C5—P1	1.794 (5)	C27—C28	1.391 (9)
C6—C7	1.387 (7)	C27—H27	0.93
C6—H6	0.93	C28—H28	0.93
C7—C8	1.373 (9)	N1—S3	1.630 (4)
C7—H7	0.93	N3—S6	1.508 (8)
C8—C9	1.370 (9)	N3—S5	1.977 (9)
C8—H8	0.93	O1—S3	1.433 (4)
C9—C10	1.378 (7)	O2—S3	1.436 (4)
C9—H9	0.93	O3—S6	1.469 (8)
C10—H10	0.93	O4—S6	1.477 (9)
C11—C12	1.383 (6)	S1—Sn1	2.5125 (12)
C11—C16	1.394 (6)	S2—Sn1	2.5262 (15)
C11—P1	1.802 (5)	S5—C3i	1.750 (12)
C12—C13	1.384 (7)	S5—Sn1	2.441 (4)
C12—H12	0.93	S4—Sn1	2.646 (3)
C13—C14	1.361 (7)	S6—O3i	1.469 (8)
C13—H13	0.93	S6—O4i	1.477 (9)
C14—C15	1.369 (7)	S6—N3i	1.508 (8)
C14—H14	0.93	S6—C4i	1.621 (11)
C15—C16	1.367 (7)	Sn1—S5i	2.441 (4)
C15—H15	0.93	Sn1—S1i	2.5125 (12)
C16—H16	0.93	Sn1—S2i	2.5262 (15)
C17—C18	1.382 (7)	Sn1—S4i	2.646 (3)
C17—C22	1.388 (7)
N1—C1—S1	117.7 (3)	C26—C25—C24	120.0 (6)
N1—C1—S2	127.2 (4)	C26—C25—H25	120
S1—C1—S2	115.1 (3)	C24—C25—H25	120
S3—C2—H2A	109.5	C27—C26—C25	120.5 (6)
S3—C2—H2B	109.5	C27—C26—H26	119.7
H2A—C2—H2B	109.5	C25—C26—H26	119.7
S3—C2—H2C	109.5	C26—C27—C28	120.7 (6)
H2A—C2—H2C	109.5	C26—C27—H27	119.7
H2B—C2—H2C	109.5	C28—C27—H27	119.7
S5—C3—N3	136.0 (15)	C23—C28—C27	119.5 (6)
S5—C3—S5i	94.5 (11)	C23—C28—H28	120.2
N3—C3—S5i	129.3 (10)	C27—C28—H28	120.2
N3—C3—S4	115.7 (9)	C1—N1—S3	122.0 (3)
S5i—C3—S4	115.0 (7)	C3—N3—O3	142.3 (10)
S6—C4—H4A	100.5	C3—N3—S6	126.4 (9)
O4i—C4—H4A	118.3	O3—N3—S5	140.2 (7)
O3—C4—H4A	126.2	S6—N3—S5	143.2 (6)
S6—C4—H4B	115	N3—O3—O4	94.0 (7)
C4i—C4—H4B	134.1	N3—O3—C4	102.9 (8)
O3—C4—H4B	115.4	C17—P1—C5	110.1 (2)
H4A—C4—H4B	118.2	C17—P1—C23	108.4 (2)
S6—C4—H4C	107	C5—P1—C23	109.6 (2)
C4i—C4—H4C	115.6	C17—P1—C11	106.7 (2)
O4i—C4—H4C	132.7	C5—P1—C11	112.4 (2)
H4A—C4—H4C	105.7	C23—P1—C11	109.6 (2)
H4B—C4—H4C	109.4	C1—S1—Sn1	86.82 (15)
C6—C5—C10	119.0 (4)	C1—S2—Sn1	86.33 (17)
C6—C5—P1	120.7 (4)	O1—S3—O2	116.2 (2)
C10—C5—P1	120.3 (4)	O1—S3—N1	111.5 (2)
C5—C6—C7	120.2 (5)	O2—S3—N1	111.1 (2)
C5—C6—H6	119.9	O1—S3—C2	108.7 (3)
C7—C6—H6	119.9	O2—S3—C2	108.5 (3)
C8—C7—C6	119.8 (6)	N1—S3—C2	99.5 (3)
C8—C7—H7	120.1	C3—S5—S4	142.7 (11)
C6—C7—H7	120.1	S4—S5—C3i	175.2 (4)
C9—C8—C7	120.8 (5)	S4—S5—N3	116.1 (3)
C9—C8—H8	119.6	C3i—S5—N3	64.0 (4)
C7—C8—H8	119.6	C3—S5—Sn1	127.1 (10)
C8—C9—C10	119.8 (5)	S4—S5—Sn1	89.6 (3)
C8—C9—H9	120.1	C3i—S5—Sn1	90.2 (5)
C10—C9—H9	120.1	N3—S5—Sn1	154.2 (3)
C9—C10—C5	120.4 (5)	S5—S4—Sn1	67.3 (3)
C9—C10—H10	119.8	C3—S4—Sn1	83.5 (4)
C5—C10—H10	119.8	O3i—S6—O3	175.2 (8)
C12—C11—C16	118.7 (4)	O3i—S6—O4	104.9 (7)
C12—C11—P1	122.6 (3)	O3—S6—O4	75.4 (7)
C16—C11—P1	118.6 (3)	O4i—S6—O4	174.6 (9)
C11—C12—C13	120.2 (4)	O3—S6—N3i	116.8 (5)
C11—C12—H12	119.9	O4i—S6—N3i	106.9 (5)
C13—C12—H12	119.9	O4—S6—N3i	77.4 (6)
C14—C13—C12	120.1 (5)	O3i—S6—N3	116.8 (5)
C14—C13—H13	119.9	O3—S6—N3	59.0 (5)
C12—C13—H13	119.9	O4i—S6—N3	77.4 (6)
C13—C14—C15	120.3 (5)	O4—S6—N3	106.9 (5)
C13—C14—H14	119.9	N3i—S6—N3	76.9 (7)
C15—C14—H14	119.9	O3i—S6—C4i	72.3 (6)
C16—C15—C14	120.5 (5)	O3—S6—C4i	112.1 (7)
C16—C15—H15	119.7	O4i—S6—C4i	103.7 (7)
C14—C15—H15	119.7	O4—S6—C4i	71.5 (6)
C15—C16—C11	120.2 (5)	N3i—S6—C4i	111.3 (6)
C15—C16—H16	119.9	N3—S6—C4i	170.6 (6)
C11—C16—H16	119.9	O3i—S6—C4	112.1 (7)
C18—C17—C22	119.3 (4)	O3—S6—C4	72.3 (6)
C18—C17—P1	119.5 (3)	O4i—S6—C4	71.5 (6)
C22—C17—P1	121.1 (4)	O4—S6—C4	103.7 (7)
C19—C18—C17	120.9 (5)	N3—S6—C4	111.3 (6)
C19—C18—H18	119.5	S5i—Sn1—S5	48.15 (19)
C17—C18—H18	119.5	S5i—Sn1—S1	97.70 (9)
C18—C19—C20	119.0 (6)	S5—Sn1—S1	100.94 (9)
C18—C19—H19	120.5	S5—Sn1—S1i	97.70 (9)
C20—C19—H19	120.5	S5i—Sn1—S2i	108.13 (10)
C21—C20—C19	120.5 (5)	S5—Sn1—S2i	152.94 (10)
C21—C20—H20	119.7	S1—Sn1—S2i	94.61 (5)
C19—C20—H20	119.7	S1i—Sn1—S2i	71.71 (4)
C20—C21—C22	120.7 (5)	S5i—Sn1—S2	152.94 (10)
C20—C21—H21	119.7	S5—Sn1—S2	108.13 (10)
C22—C21—H21	119.7	S1—Sn1—S2	71.71 (4)
C21—C22—C17	119.5 (5)	S1i—Sn1—S2	94.61 (5)
C21—C22—H22	120.2	S5—Sn1—S4i	71.14 (14)
C17—C22—H22	120.2	S1—Sn1—S4i	96.17 (7)
C28—C23—C24	119.5 (5)	S2i—Sn1—S4i	85.36 (8)
C28—C23—P1	119.3 (4)	S2—Sn1—S4i	167.66 (7)
C24—C23—P1	121.0 (4)	S1—Sn1—S4	97.69 (8)
C23—C24—C25	119.8 (5)	S1i—Sn1—S4	96.17 (7)
C23—C24—H24	120.1	S2i—Sn1—S4	167.66 (7)
C25—C24—H24	120.1	S2—Sn1—S4	85.36 (8)
C10—C5—C6—C7	−1.3 (8)	C3i—C3—N3—S6	5.2 (18)
P1—C5—C6—C7	−179.2 (4)	S5i—C3—N3—S6	5.2 (15)
C5—C6—C7—C8	0.6 (9)	S4—C3—N3—S6	−175.4 (6)
C6—C7—C8—C9	0.3 (9)	S4—C3—N3—N3i	−177.0 (8)
C7—C8—C9—C10	−0.5 (9)	C3i—C3—N3—S5	−173 (3)
C8—C9—C10—C5	−0.2 (8)	S5i—C3—N3—S5	−173 (3)
C6—C5—C10—C9	1.1 (7)	S4—C3—N3—S5	6.0 (12)
P1—C5—C10—C9	179.1 (4)	C18—C17—P1—C5	−70.6 (4)
C16—C11—C12—C13	−1.2 (7)	C22—C17—P1—C5	112.8 (4)
P1—C11—C12—C13	−176.7 (4)	C18—C17—P1—C23	169.5 (4)
C11—C12—C13—C14	0.5 (8)	C22—C17—P1—C23	−7.1 (4)
C12—C13—C14—C15	0.2 (8)	C18—C17—P1—C11	51.6 (4)
C13—C14—C15—C16	−0.3 (9)	C22—C17—P1—C11	−125.0 (4)
C14—C15—C16—C11	−0.4 (9)	C6—C5—P1—C17	2.9 (5)
C12—C11—C16—C15	1.1 (8)	C10—C5—P1—C17	−175.1 (4)
P1—C11—C16—C15	176.8 (4)	C6—C5—P1—C23	122.0 (4)
C22—C17—C18—C19	0.3 (7)	C10—C5—P1—C23	−55.9 (4)
P1—C17—C18—C19	−176.3 (4)	C6—C5—P1—C11	−115.9 (4)
C17—C18—C19—C20	0.0 (8)	C10—C5—P1—C11	66.2 (4)
C18—C19—C20—C21	−0.1 (8)	C28—C23—P1—C17	−71.1 (5)
C19—C20—C21—C22	−0.2 (8)	C24—C23—P1—C17	103.7 (5)
C20—C21—C22—C17	0.5 (8)	C28—C23—P1—C5	168.7 (5)
C18—C17—C22—C21	−0.5 (7)	C24—C23—P1—C5	−16.5 (5)
P1—C17—C22—C21	176.1 (4)	C28—C23—P1—C11	45.0 (5)
C28—C23—C24—C25	0.9 (9)	C24—C23—P1—C11	−140.3 (4)
P1—C23—C24—C25	−173.9 (5)	C12—C11—P1—C17	−157.2 (4)
C23—C24—C25—C26	0.7 (11)	C16—C11—P1—C17	27.3 (5)
C24—C25—C26—C27	−1.0 (13)	C12—C11—P1—C5	−36.4 (5)
C25—C26—C27—C28	−0.3 (14)	C16—C11—P1—C5	148.1 (4)
C24—C23—C28—C27	−2.2 (10)	C12—C11—P1—C23	85.7 (5)
P1—C23—C28—C27	172.7 (6)	C16—C11—P1—C23	−89.8 (4)
C26—C27—C28—C23	2.0 (13)	N1—C1—S1—Sn1	178.7 (4)
S1—C1—N1—S3	179.5 (2)	S2—C1—S1—Sn1	−2.4 (2)
S2—C1—N1—S3	0.7 (6)	N1—C1—S2—Sn1	−178.8 (4)
S5—C3—N3—O3	94 (2)	S1—C1—S2—Sn1	2.4 (2)
C3i—C3—N3—O3	−80 (2)	C1—N1—S3—O1	−60.3 (5)
S4—C3—N3—O3	99.6 (15)	C1—N1—S3—O2	71.0 (5)
S5—C3—N3—S6	178.6 (15)	C1—N1—S3—C2	−174.8 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O4ii	0.96	2.35	3.284 (13)	166
C16—H16···O3iii	0.93	2.60	3.2203 (10)	125
C19—H19···O1iv	0.93	2.47	3.296 (7)	148
C28—H28···S4iii	0.93	2.69	3.345 (5)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯O4i	0.96	2.35	3.284 (13)	166
C16—H16⋯O3ii	0.93	2.60	3.2203 (10)	125
C19—H19⋯O1iii	0.93	2.47	3.296 (7)	148
C28—H28⋯S4ii	0.93	2.69	3.345 (5)	128

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