Bis(μ(2)-4-amino-3-nitro-benzoato)bis-(4-amino-3-nitro-benzoato)octa-butyldi-μ(3)-oxido-tetra-tin(IV).

The tetranuclear molecules of the title compound, [Sn(4)(C(4)H(9))(8)(C(7)H(5)N(2)O(4))(4)O(2)], reside on a crystallographic inversion center. Both the two independent Sn atoms are five-coordinate, with distorted trigonal-bipyramidal geometries. One Sn atom is coordinated by two O atoms of the carboxyl-ate anions, one bridging O atom and two butyl groups and the other Sn atom is coordinated by an O atom of the carboxyl-ate anion, two bridging O atoms and two butyl groups. All the butyl groups are equatorial with respect to the SnO(3) trigonal plane. The mol-ecular structure is stabilized by intra-molecular N-H⋯O hydrogen bonds. In the crystal, pairs of inter-molecular bifurcated acceptor N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into chains along [10]. Weak inter-molecular C-H⋯π and π-π inter-actions [centroid-centroid distance = 3.713 (2) Å] are also observed.

Related literature

For general background to and applications of the title complex, see: Khoo & Hazell (1999 ▶); Parvez et al. (2004 ▶); Li et al. (2006 ▶); Win et al. (2008a ▶,b ▶). For closely related structures, see: Khoo & Hazell (1999 ▶); Parvez et al. (2004 ▶); Li et al. (2006 ▶); Win et al. (2008b ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

[Sn4(C4H9)8(C7H5N2O4)4O2]

M = 1688.18

Triclinic,

a = 11.9585 (9) Å

b = 13.0679 (10) Å

c = 13.1897 (10) Å

α = 76.256 (2)°

β = 67.445 (2)°

γ = 66.108 (2)°

V = 1732.1 (2) Å3

Z = 1

Mo Kα radiation

μ = 1.50 mm−1

T = 100 K

0.20 × 0.15 × 0.06 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.758, T max = 0.912

32184 measured reflections

11359 independent reflections

8603 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.116

S = 1.04

11359 reflections

410 parameters

H-atom parameters constrained

Δρmax = 1.26 e Å−3

Δρmin = −1.18 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810040146/fj2350sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040146/fj2350Isup2.hkl

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

[Sn4(C4H9)8(C7H5N2O4)4O2]	Z = 1
Mr = 1688.18	F(000) = 852
Triclinic, P1	Dx = 1.618 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.9585 (9) Å	Cell parameters from 5645 reflections
b = 13.0679 (10) Å	θ = 3.4–33.2°
c = 13.1897 (10) Å	µ = 1.50 mm−1
α = 76.256 (2)°	T = 100 K
β = 67.445 (2)°	Block, yellow
γ = 66.108 (2)°	0.20 × 0.15 × 0.06 mm
V = 1732.1 (2) Å3

Bruker APEXII DUO CCD area-detector diffractometer	11359 independent reflections
Radiation source: fine-focus sealed tube	8603 reflections with I > 2σ(I)
graphite	Rint = 0.055
φ and ω scans	θmax = 31.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→17
Tmin = 0.758, Tmax = 0.912	k = −19→18
32184 measured reflections	l = −19→19

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0611P)2] where P = (Fo2 + 2Fc2)/3
11359 reflections	(Δ/σ)max = 0.001
410 parameters	Δρmax = 1.25 e Å−3
0 restraints	Δρmin = −1.17 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	−0.15407 (2)	0.426491 (18)	0.258267 (17)	0.01235 (6)
Sn2	0.126384 (19)	0.388757 (17)	0.012249 (17)	0.01183 (6)
O1	0.5285 (3)	−0.1013 (3)	0.4294 (3)	0.0452 (9)
O2	0.3268 (4)	−0.0394 (3)	0.5298 (3)	0.0469 (9)
O3	0.0372 (2)	0.29294 (19)	0.21639 (19)	0.0150 (5)
O4	−0.0160 (2)	0.2104 (2)	0.3863 (2)	0.0230 (5)
O5	0.9029 (2)	−0.0002 (2)	−0.1901 (2)	0.0233 (5)
O6	0.7210 (3)	0.0470 (2)	−0.0558 (2)	0.0254 (6)
O7	0.3299 (2)	0.3217 (2)	−0.10236 (19)	0.0183 (5)
O8	−0.3316 (2)	0.5805 (2)	0.2675 (2)	0.0187 (5)
O9	−0.0734 (2)	0.47928 (19)	0.09963 (18)	0.0133 (4)
N1	0.5993 (3)	−0.0496 (3)	0.2134 (3)	0.0313 (8)
H1N1	0.6573	−0.0435	0.1450	0.038*
H2N1	0.6222	−0.0939	0.2830	0.038*
N2	0.4123 (4)	−0.0430 (3)	0.4400 (3)	0.0315 (8)
N3	0.9151 (3)	0.0899 (3)	−0.3964 (2)	0.0192 (6)
H1N3	0.9467	0.1258	−0.4600	0.023*
H2N3	0.9574	0.0317	−0.3594	0.023*
N4	0.7854 (3)	0.0571 (2)	−0.1543 (2)	0.0173 (6)
C1	0.2968 (3)	0.1390 (3)	0.1681 (3)	0.0186 (7)
H1A	0.2693	0.1787	0.1084	0.022*
C2	0.4240 (3)	0.0748 (3)	0.1495 (3)	0.0212 (7)
H2A	0.4809	0.0718	0.0776	0.025*
C3	0.4715 (3)	0.0126 (3)	0.2369 (3)	0.0213 (7)
C4	0.3797 (4)	0.0193 (3)	0.3434 (3)	0.0211 (7)
C5	0.2486 (3)	0.0864 (3)	0.3609 (3)	0.0182 (6)
H5A	0.1902	0.0895	0.4322	0.022*
C6	0.2058 (3)	0.1470 (3)	0.2745 (3)	0.0163 (6)
C7	0.0658 (3)	0.2188 (3)	0.2964 (3)	0.0161 (6)
C8	−0.2737 (3)	0.3386 (3)	0.2691 (3)	0.0190 (7)
H8A	−0.3379	0.3446	0.3420	0.023*
H8B	−0.3195	0.3771	0.2164	0.023*
C9	−0.2096 (4)	0.2138 (3)	0.2494 (3)	0.0238 (7)
H9A	−0.1820	0.1707	0.3118	0.029*
H9B	−0.1334	0.2038	0.1843	0.029*
C10	−0.3018 (4)	0.1683 (3)	0.2336 (4)	0.0283 (8)
H10A	−0.2612	0.0875	0.2313	0.034*
H10B	−0.3802	0.1828	0.2968	0.034*
C11	−0.3378 (6)	0.2205 (5)	0.1287 (4)	0.0438 (12)
H11A	−0.3958	0.1894	0.1240	0.066*
H11B	−0.2611	0.2043	0.0655	0.066*
H11C	−0.3793	0.3004	0.1307	0.066*
C12	−0.1180 (3)	0.4888 (3)	0.3732 (3)	0.0191 (7)
H12A	−0.0676	0.4252	0.4117	0.023*
H12B	−0.0650	0.5344	0.3321	0.023*
C13	−0.2355 (4)	0.5582 (4)	0.4589 (3)	0.0248 (8)
H13A	−0.2862	0.6223	0.4211	0.030*
H13B	−0.2886	0.5128	0.5010	0.030*
C14	−0.2041 (4)	0.6002 (4)	0.5377 (3)	0.0280 (8)
H14A	−0.1521	0.6466	0.4963	0.034*
H14B	−0.1533	0.5365	0.5758	0.034*
C15	−0.3241 (5)	0.6682 (4)	0.6222 (4)	0.0352 (10)
H15A	−0.2992	0.6927	0.6707	0.053*
H15B	−0.3754	0.6224	0.6644	0.053*
H15C	−0.3737	0.7325	0.5851	0.053*
C16	0.5905 (3)	0.2917 (3)	−0.3655 (3)	0.0166 (6)
H16A	0.5465	0.3451	−0.4107	0.020*
C17	0.7173 (3)	0.2297 (3)	−0.4104 (3)	0.0178 (6)
H17A	0.7574	0.2407	−0.4859	0.021*
C18	0.7904 (3)	0.1483 (3)	−0.3449 (3)	0.0152 (6)
C19	0.7236 (3)	0.1349 (3)	−0.2307 (3)	0.0135 (6)
C20	0.5918 (3)	0.1990 (3)	−0.1861 (3)	0.0133 (6)
H20A	0.5499	0.1885	−0.1109	0.016*
C21	0.5243 (3)	0.2764 (3)	−0.2514 (3)	0.0136 (6)
C22	0.3840 (3)	0.3441 (3)	−0.2034 (3)	0.0138 (6)
C23	0.0916 (4)	0.2564 (3)	−0.0232 (3)	0.0194 (7)
H23A	0.1537	0.1853	−0.0055	0.023*
H23B	0.0061	0.2570	0.0241	0.023*
C24	0.1005 (3)	0.2635 (3)	−0.1432 (3)	0.0183 (6)
H24A	0.0363	0.3332	−0.1604	0.022*
H24B	0.1850	0.2651	−0.1908	0.022*
C25	0.0794 (4)	0.1652 (3)	−0.1674 (3)	0.0215 (7)
H25A	0.1367	0.0952	−0.1421	0.026*
H25B	−0.0088	0.1689	−0.1266	0.026*
C26	0.1044 (4)	0.1659 (4)	−0.2894 (4)	0.0301 (9)
H26A	0.1004	0.0983	−0.3020	0.045*
H26B	0.1885	0.1701	−0.3309	0.045*
H26C	0.0400	0.2299	−0.3125	0.045*
C27	0.2107 (3)	0.4357 (3)	0.1018 (3)	0.0174 (6)
H27A	0.1436	0.4668	0.1682	0.021*
H27B	0.2737	0.3685	0.1245	0.021*
C28	0.2768 (4)	0.5210 (3)	0.0386 (3)	0.0202 (7)
H28A	0.3422	0.4917	−0.0292	0.024*
H28B	0.2134	0.5900	0.0189	0.024*
C29	0.3397 (3)	0.5474 (3)	0.1050 (3)	0.0221 (7)
H29A	0.3960	0.4773	0.1313	0.027*
H29B	0.3931	0.5906	0.0567	0.027*
C30	0.2445 (4)	0.6125 (4)	0.2031 (3)	0.0269 (8)
H30A	0.2908	0.6194	0.2452	0.040*
H30B	0.1869	0.5733	0.2487	0.040*
H30C	0.1957	0.6860	0.1774	0.040*

	U11	U22	U33	U12	U13	U23
Sn1	0.01042 (10)	0.01296 (11)	0.01006 (10)	−0.00221 (7)	−0.00232 (7)	0.00013 (8)
Sn2	0.01123 (10)	0.01097 (10)	0.01065 (10)	−0.00180 (7)	−0.00337 (7)	−0.00046 (7)
O1	0.0303 (17)	0.047 (2)	0.053 (2)	0.0028 (14)	−0.0281 (16)	−0.0003 (17)
O2	0.042 (2)	0.059 (2)	0.0247 (16)	−0.0027 (16)	−0.0162 (15)	0.0049 (15)
O3	0.0112 (10)	0.0149 (11)	0.0138 (10)	−0.0025 (8)	−0.0021 (8)	0.0003 (9)
O4	0.0167 (12)	0.0256 (14)	0.0165 (12)	−0.0040 (9)	−0.0023 (10)	0.0045 (10)
O5	0.0134 (11)	0.0237 (13)	0.0247 (13)	0.0002 (9)	−0.0071 (10)	0.0013 (10)
O6	0.0214 (13)	0.0294 (15)	0.0150 (12)	−0.0009 (10)	−0.0053 (10)	0.0010 (10)
O7	0.0117 (11)	0.0233 (13)	0.0119 (10)	−0.0004 (9)	−0.0021 (9)	−0.0007 (9)
O8	0.0135 (11)	0.0199 (12)	0.0174 (11)	0.0010 (9)	−0.0068 (9)	−0.0017 (9)
O9	0.0116 (10)	0.0127 (10)	0.0117 (10)	−0.0025 (8)	−0.0029 (8)	0.0009 (8)
N1	0.0133 (14)	0.0299 (18)	0.043 (2)	−0.0003 (12)	−0.0082 (14)	−0.0053 (16)
N2	0.0276 (18)	0.0309 (19)	0.0340 (19)	−0.0016 (13)	−0.0198 (15)	0.0013 (15)
N3	0.0104 (12)	0.0188 (14)	0.0184 (14)	−0.0006 (10)	−0.0018 (10)	0.0026 (11)
N4	0.0149 (13)	0.0170 (14)	0.0190 (14)	−0.0021 (10)	−0.0088 (11)	−0.0010 (11)
C1	0.0141 (15)	0.0159 (15)	0.0233 (17)	−0.0039 (11)	−0.0057 (13)	−0.0005 (13)
C2	0.0146 (15)	0.0217 (17)	0.0237 (17)	−0.0053 (12)	−0.0027 (13)	−0.0040 (14)
C3	0.0149 (15)	0.0163 (16)	0.0331 (19)	−0.0041 (12)	−0.0078 (14)	−0.0057 (14)
C4	0.0245 (18)	0.0179 (16)	0.0251 (17)	−0.0081 (13)	−0.0140 (14)	0.0015 (14)
C5	0.0148 (15)	0.0182 (16)	0.0206 (16)	−0.0051 (11)	−0.0073 (13)	0.0014 (13)
C6	0.0118 (14)	0.0142 (15)	0.0217 (16)	−0.0041 (11)	−0.0051 (12)	−0.0011 (12)
C7	0.0144 (14)	0.0132 (15)	0.0188 (15)	−0.0019 (11)	−0.0089 (12)	0.0025 (12)
C8	0.0149 (15)	0.0174 (16)	0.0218 (16)	−0.0056 (11)	−0.0040 (13)	−0.0006 (13)
C9	0.0226 (17)	0.0192 (17)	0.0300 (19)	−0.0075 (13)	−0.0078 (15)	−0.0041 (15)
C10	0.033 (2)	0.0203 (18)	0.034 (2)	−0.0134 (15)	−0.0121 (17)	0.0024 (16)
C11	0.066 (4)	0.041 (3)	0.047 (3)	−0.034 (3)	−0.031 (3)	0.004 (2)
C12	0.0168 (15)	0.0209 (17)	0.0175 (15)	−0.0020 (12)	−0.0073 (12)	−0.0038 (13)
C13	0.0201 (17)	0.033 (2)	0.0234 (18)	−0.0076 (14)	−0.0060 (14)	−0.0104 (16)
C14	0.035 (2)	0.033 (2)	0.0184 (17)	−0.0131 (16)	−0.0098 (16)	−0.0030 (15)
C15	0.043 (3)	0.035 (2)	0.026 (2)	−0.0060 (18)	−0.0123 (19)	−0.0121 (18)
C16	0.0147 (14)	0.0166 (15)	0.0148 (14)	−0.0032 (11)	−0.0048 (12)	0.0011 (12)
C17	0.0132 (14)	0.0192 (16)	0.0143 (14)	−0.0013 (11)	−0.0035 (12)	0.0003 (12)
C18	0.0118 (13)	0.0148 (15)	0.0173 (15)	−0.0048 (11)	−0.0034 (12)	−0.0007 (12)
C19	0.0121 (13)	0.0130 (14)	0.0159 (14)	−0.0039 (10)	−0.0060 (11)	−0.0007 (11)
C20	0.0124 (13)	0.0141 (14)	0.0122 (13)	−0.0048 (10)	−0.0026 (11)	−0.0014 (11)
C21	0.0102 (13)	0.0144 (14)	0.0117 (13)	−0.0014 (10)	−0.0012 (11)	−0.0026 (11)
C22	0.0132 (14)	0.0122 (14)	0.0168 (14)	−0.0028 (10)	−0.0061 (11)	−0.0038 (12)
C23	0.0211 (16)	0.0192 (16)	0.0171 (15)	−0.0079 (12)	−0.0042 (13)	−0.0024 (13)
C24	0.0202 (16)	0.0174 (16)	0.0195 (16)	−0.0063 (12)	−0.0090 (13)	−0.0020 (13)
C25	0.0188 (16)	0.0197 (17)	0.0275 (18)	−0.0053 (12)	−0.0076 (14)	−0.0073 (14)
C26	0.026 (2)	0.035 (2)	0.034 (2)	−0.0072 (15)	−0.0130 (17)	−0.0120 (18)
C27	0.0165 (15)	0.0186 (16)	0.0169 (15)	−0.0079 (12)	−0.0040 (12)	−0.0006 (12)
C28	0.0233 (17)	0.0228 (17)	0.0164 (15)	−0.0126 (13)	−0.0053 (13)	0.0007 (13)
C29	0.0185 (16)	0.0252 (18)	0.0259 (18)	−0.0125 (13)	−0.0081 (14)	0.0020 (14)
C30	0.0252 (19)	0.029 (2)	0.033 (2)	−0.0119 (15)	−0.0110 (16)	−0.0075 (17)

Sn1—O9	2.022 (2)	C11—H11C	0.9600
Sn1—C8	2.117 (4)	C12—C13	1.520 (5)
Sn1—C12	2.125 (3)	C12—H12A	0.9700
Sn1—O3	2.200 (2)	C12—H12B	0.9700
Sn1—O8	2.243 (2)	C13—C14	1.504 (5)
Sn2—O9i	2.044 (2)	C13—H13A	0.9700
Sn2—C23	2.121 (3)	C13—H13B	0.9700
Sn2—C27	2.133 (3)	C14—C15	1.517 (6)
Sn2—O9	2.163 (2)	C14—H14A	0.9700
Sn2—O7	2.249 (2)	C14—H14B	0.9700
Sn2—Sn2i	3.2982 (4)	C15—H15A	0.9600
O1—N2	1.255 (5)	C15—H15B	0.9600
O2—N2	1.228 (5)	C15—H15C	0.9600
O3—C7	1.301 (4)	C16—C17	1.360 (4)
O4—C7	1.229 (4)	C16—C21	1.415 (4)
O5—N4	1.251 (4)	C16—H16A	0.9300
O6—N4	1.238 (4)	C17—C18	1.425 (5)
O7—C22	1.260 (4)	C17—H17A	0.9300
O8—C22i	1.260 (4)	C18—C19	1.415 (5)
O9—Sn2i	2.044 (2)	C19—C20	1.409 (4)
N1—C3	1.357 (5)	C20—C21	1.369 (5)
N1—H1N1	0.9127	C20—H20A	0.9300
N1—H2N1	1.0326	C21—C22	1.499 (4)
N2—C4	1.439 (5)	C22—O8i	1.260 (4)
N3—C18	1.348 (4)	C23—C24	1.527 (5)
N3—H1N3	0.8828	C23—H23A	0.9700
N3—H2N3	0.8795	C23—H23B	0.9700
N4—C19	1.439 (4)	C24—C25	1.527 (5)
C1—C2	1.363 (5)	C24—H24A	0.9700
C1—C6	1.404 (5)	C24—H24B	0.9700
C1—H1A	0.9300	C25—C26	1.518 (6)
C2—C3	1.413 (6)	C25—H25A	0.9700
C2—H2A	0.9300	C25—H25B	0.9700
C3—C4	1.408 (5)	C26—H26A	0.9600
C4—C5	1.408 (5)	C26—H26B	0.9600
C5—C6	1.371 (5)	C26—H26C	0.9600
C5—H5A	0.9300	C27—C28	1.526 (5)
C6—C7	1.500 (5)	C27—H27A	0.9700
C8—C9	1.533 (5)	C27—H27B	0.9700
C8—H8A	0.9700	C28—C29	1.521 (5)
C8—H8B	0.9700	C28—H28A	0.9700
C9—C10	1.543 (6)	C28—H28B	0.9700
C9—H9A	0.9700	C29—C30	1.517 (5)
C9—H9B	0.9700	C29—H29A	0.9700
C10—C11	1.528 (7)	C29—H29B	0.9700
C10—H10A	0.9700	C30—H30A	0.9600
C10—H10B	0.9700	C30—H30B	0.9600
C11—H11A	0.9600	C30—H30C	0.9600
C11—H11B	0.9600
O9—Sn1—C8	110.89 (12)	C13—C12—H12B	108.1
O9—Sn1—C12	113.25 (12)	Sn1—C12—H12B	108.1
C8—Sn1—C12	135.33 (14)	H12A—C12—H12B	107.3
O9—Sn1—O3	78.94 (9)	C14—C13—C12	114.5 (3)
C8—Sn1—O3	100.88 (11)	C14—C13—H13A	108.6
C12—Sn1—O3	93.91 (11)	C12—C13—H13A	108.6
O9—Sn1—O8	89.41 (9)	C14—C13—H13B	108.6
C8—Sn1—O8	84.97 (12)	C12—C13—H13B	108.6
C12—Sn1—O8	88.89 (11)	H13A—C13—H13B	107.6
O3—Sn1—O8	168.19 (9)	C13—C14—C15	112.6 (4)
O9i—Sn2—C23	104.84 (12)	C13—C14—H14A	109.1
O9i—Sn2—C27	108.28 (12)	C15—C14—H14A	109.1
C23—Sn2—C27	146.36 (14)	C13—C14—H14B	109.1
O9i—Sn2—O9	76.78 (9)	C15—C14—H14B	109.1
C23—Sn2—O9	95.98 (11)	H14A—C14—H14B	107.8
C27—Sn2—O9	97.07 (11)	C14—C15—H15A	109.5
O9i—Sn2—O7	92.75 (9)	C14—C15—H15B	109.5
C23—Sn2—O7	87.89 (12)	H15A—C15—H15B	109.5
C27—Sn2—O7	84.87 (11)	C14—C15—H15C	109.5
O9—Sn2—O7	169.46 (9)	H15A—C15—H15C	109.5
O9i—Sn2—Sn2i	39.68 (6)	H15B—C15—H15C	109.5
C23—Sn2—Sn2i	103.12 (10)	C17—C16—C21	121.3 (3)
C27—Sn2—Sn2i	105.97 (10)	C17—C16—H16A	119.4
O9—Sn2—Sn2i	37.10 (6)	C21—C16—H16A	119.4
O7—Sn2—Sn2i	132.42 (6)	C16—C17—C18	121.9 (3)
C7—O3—Sn1	116.89 (19)	C16—C17—H17A	119.1
C22—O7—Sn2	133.4 (2)	C18—C17—H17A	119.1
C22i—O8—Sn1	139.1 (2)	N3—C18—C19	125.8 (3)
Sn1—O9—Sn2i	137.06 (11)	N3—C18—C17	117.9 (3)
Sn1—O9—Sn2	119.61 (11)	C19—C18—C17	116.3 (3)
Sn2i—O9—Sn2	103.22 (9)	C20—C19—C18	120.9 (3)
C3—N1—H1N1	121.9	C20—C19—N4	116.6 (3)
C3—N1—H2N1	112.1	C18—C19—N4	122.5 (3)
H1N1—N1—H2N1	125.5	C21—C20—C19	121.3 (3)
O2—N2—O1	121.7 (4)	C21—C20—H20A	119.4
O2—N2—C4	119.9 (3)	C19—C20—H20A	119.4
O1—N2—C4	118.4 (4)	C20—C21—C16	118.3 (3)
C18—N3—H1N3	111.7	C20—C21—C22	121.0 (3)
C18—N3—H2N3	118.7	C16—C21—C22	120.7 (3)
H1N3—N3—H2N3	128.4	O7—C22—O8i	126.0 (3)
O6—N4—O5	121.8 (3)	O7—C22—C21	117.0 (3)
O6—N4—C19	119.5 (3)	O8i—C22—C21	117.0 (3)
O5—N4—C19	118.7 (3)	C24—C23—Sn2	114.1 (2)
C2—C1—C6	122.2 (4)	C24—C23—H23A	108.7
C2—C1—H1A	118.9	Sn2—C23—H23A	108.7
C6—C1—H1A	118.9	C24—C23—H23B	108.7
C1—C2—C3	121.5 (3)	Sn2—C23—H23B	108.7
C1—C2—H2A	119.3	H23A—C23—H23B	107.6
C3—C2—H2A	119.3	C25—C24—C23	113.0 (3)
N1—C3—C4	124.9 (4)	C25—C24—H24A	109.0
N1—C3—C2	118.9 (4)	C23—C24—H24A	109.0
C4—C3—C2	116.2 (3)	C25—C24—H24B	109.0
C3—C4—C5	121.4 (4)	C23—C24—H24B	109.0
C3—C4—N2	122.7 (3)	H24A—C24—H24B	107.8
C5—C4—N2	115.9 (3)	C26—C25—C24	112.3 (3)
C6—C5—C4	121.0 (3)	C26—C25—H25A	109.1
C6—C5—H5A	119.5	C24—C25—H25A	109.1
C4—C5—H5A	119.5	C26—C25—H25B	109.1
C5—C6—C1	117.7 (3)	C24—C25—H25B	109.1
C5—C6—C7	119.6 (3)	H25A—C25—H25B	107.9
C1—C6—C7	122.7 (3)	C25—C26—H26A	109.5
O4—C7—O3	122.2 (3)	C25—C26—H26B	109.5
O4—C7—C6	121.6 (3)	H26A—C26—H26B	109.5
O3—C7—C6	116.2 (3)	C25—C26—H26C	109.5
C9—C8—Sn1	118.1 (2)	H26A—C26—H26C	109.5
C9—C8—H8A	107.8	H26B—C26—H26C	109.5
Sn1—C8—H8A	107.8	C28—C27—Sn2	115.0 (2)
C9—C8—H8B	107.8	C28—C27—H27A	108.5
Sn1—C8—H8B	107.8	Sn2—C27—H27A	108.5
H8A—C8—H8B	107.1	C28—C27—H27B	108.5
C8—C9—C10	112.1 (3)	Sn2—C27—H27B	108.5
C8—C9—H9A	109.2	H27A—C27—H27B	107.5
C10—C9—H9A	109.2	C29—C28—C27	112.5 (3)
C8—C9—H9B	109.2	C29—C28—H28A	109.1
C10—C9—H9B	109.2	C27—C28—H28A	109.1
H9A—C9—H9B	107.9	C29—C28—H28B	109.1
C11—C10—C9	113.5 (4)	C27—C28—H28B	109.1
C11—C10—H10A	108.9	H28A—C28—H28B	107.8
C9—C10—H10A	108.9	C30—C29—C28	114.2 (3)
C11—C10—H10B	108.9	C30—C29—H29A	108.7
C9—C10—H10B	108.9	C28—C29—H29A	108.7
H10A—C10—H10B	107.7	C30—C29—H29B	108.7
C10—C11—H11A	109.5	C28—C29—H29B	108.7
C10—C11—H11B	109.5	H29A—C29—H29B	107.6
H11A—C11—H11B	109.5	C29—C30—H30A	109.5
C10—C11—H11C	109.5	C29—C30—H30B	109.5
H11A—C11—H11C	109.5	H30A—C30—H30B	109.5
H11B—C11—H11C	109.5	C29—C30—H30C	109.5
C13—C12—Sn1	116.8 (2)	H30A—C30—H30C	109.5
C13—C12—H12A	108.1	H30B—C30—H30C	109.5
Sn1—C12—H12A	108.1
O9—Sn1—O3—C7	173.3 (3)	C5—C6—C7—O3	164.7 (3)
C8—Sn1—O3—C7	−77.3 (3)	C1—C6—C7—O3	−15.1 (5)
C12—Sn1—O3—C7	60.4 (3)	O9—Sn1—C8—C9	83.0 (3)
O8—Sn1—O3—C7	163.8 (4)	C12—Sn1—C8—C9	−106.3 (3)
O9i—Sn2—O7—C22	−11.5 (3)	O3—Sn1—C8—C9	0.8 (3)
C23—Sn2—O7—C22	93.3 (3)	O8—Sn1—C8—C9	170.4 (3)
C27—Sn2—O7—C22	−119.6 (3)	Sn1—C8—C9—C10	−166.9 (3)
O9—Sn2—O7—C22	−18.5 (7)	C8—C9—C10—C11	66.1 (5)
Sn2i—Sn2—O7—C22	−12.6 (4)	O9—Sn1—C12—C13	121.2 (3)
O9—Sn1—O8—C22i	17.1 (4)	C8—Sn1—C12—C13	−49.4 (4)
C8—Sn1—O8—C22i	−94.0 (4)	O3—Sn1—C12—C13	−159.2 (3)
C12—Sn1—O8—C22i	130.3 (4)	O8—Sn1—C12—C13	32.3 (3)
O3—Sn1—O8—C22i	26.4 (7)	Sn1—C12—C13—C14	−179.8 (3)
C8—Sn1—O9—Sn2i	82.2 (2)	C12—C13—C14—C15	−179.6 (4)
C12—Sn1—O9—Sn2i	−90.8 (2)	C21—C16—C17—C18	−1.4 (5)
O3—Sn1—O9—Sn2i	179.71 (19)	C16—C17—C18—N3	179.4 (3)
O8—Sn1—O9—Sn2i	−2.23 (18)	C16—C17—C18—C19	0.4 (5)
C8—Sn1—O9—Sn2	−102.47 (15)	N3—C18—C19—C20	−178.5 (3)
C12—Sn1—O9—Sn2	84.59 (15)	C17—C18—C19—C20	0.4 (5)
O3—Sn1—O9—Sn2	−4.93 (11)	N3—C18—C19—N4	2.1 (5)
O8—Sn1—O9—Sn2	173.13 (13)	C17—C18—C19—N4	−179.1 (3)
O9i—Sn2—O9—Sn1	−176.76 (19)	O6—N4—C19—C20	2.5 (5)
C23—Sn2—O9—Sn1	79.36 (15)	O5—N4—C19—C20	−178.9 (3)
C27—Sn2—O9—Sn1	−69.56 (15)	O6—N4—C19—C18	−178.0 (3)
O7—Sn2—O9—Sn1	−169.5 (4)	O5—N4—C19—C18	0.6 (5)
Sn2i—Sn2—O9—Sn1	−176.76 (19)	C18—C19—C20—C21	−0.3 (5)
O9i—Sn2—O9—Sn2i	0.001 (2)	N4—C19—C20—C21	179.2 (3)
C23—Sn2—O9—Sn2i	−103.88 (13)	C19—C20—C21—C16	−0.6 (5)
C27—Sn2—O9—Sn2i	107.20 (13)	C19—C20—C21—C22	179.9 (3)
O7—Sn2—O9—Sn2i	7.2 (5)	C17—C16—C21—C20	1.4 (5)
C6—C1—C2—C3	−0.1 (6)	C17—C16—C21—C22	−179.0 (3)
C1—C2—C3—N1	−179.8 (4)	Sn2—O7—C22—O8i	3.3 (5)
C1—C2—C3—C4	1.1 (5)	Sn2—O7—C22—C21	−178.0 (2)
N1—C3—C4—C5	179.8 (4)	C20—C21—C22—O7	−4.1 (5)
C2—C3—C4—C5	−1.3 (5)	C16—C21—C22—O7	176.3 (3)
N1—C3—C4—N2	−1.7 (6)	C20—C21—C22—O8i	174.7 (3)
C2—C3—C4—N2	177.3 (3)	C16—C21—C22—O8i	−4.9 (5)
O2—N2—C4—C3	−175.4 (4)	O9i—Sn2—C23—C24	27.4 (3)
O1—N2—C4—C3	3.5 (6)	C27—Sn2—C23—C24	−142.4 (2)
O2—N2—C4—C5	3.2 (6)	O9—Sn2—C23—C24	105.2 (2)
O1—N2—C4—C5	−177.9 (4)	O7—Sn2—C23—C24	−64.9 (3)
C3—C4—C5—C6	0.4 (5)	Sn2i—Sn2—C23—C24	68.3 (3)
N2—C4—C5—C6	−178.2 (3)	Sn2—C23—C24—C25	178.1 (2)
C4—C5—C6—C1	0.7 (5)	C23—C24—C25—C26	−173.1 (3)
C4—C5—C6—C7	−179.1 (3)	O9i—Sn2—C27—C28	−28.8 (3)
C2—C1—C6—C5	−0.8 (5)	C23—Sn2—C27—C28	140.8 (3)
C2—C1—C6—C7	179.0 (3)	O9—Sn2—C27—C28	−107.1 (2)
Sn1—O3—C7—O4	12.7 (4)	O7—Sn2—C27—C28	62.5 (2)
Sn1—O3—C7—C6	−164.9 (2)	Sn2i—Sn2—C27—C28	−70.3 (2)
C5—C6—C7—O4	−12.8 (5)	Sn2—C27—C28—C29	−177.6 (2)
C1—C6—C7—O4	167.4 (3)	C27—C28—C29—C30	−68.9 (4)

Cg1 is the centroid of the C16–C21 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O6	0.91	2.59	3.422 (4)	153
N1—H2N1···O1	1.03	1.83	2.644 (5)	133
N3—H1N3···O4ii	0.88	2.04	2.910 (4)	167
N3—H2N3···O5	0.88	2.06	2.669 (4)	125
C17—H17A···O4ii	0.93	2.51	3.246 (5)	137
C30—H30A···Cg1iii	0.96	2.80	3.584 (5)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C16–C21 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O6	0.91	2.59	3.422 (4)	153
N1—H2N1⋯O1	1.03	1.83	2.644 (5)	133
N3—H1N3⋯O4i	0.88	2.04	2.910 (4)	167
N3—H2N3⋯O5	0.88	2.06	2.669 (4)	125
C17—H17A⋯O4i	0.93	2.51	3.246 (5)	137
C30—H30A⋯Cg1ii	0.96	2.80	3.584 (5)	139

Symmetry codes: (i) ; (ii) .