{4-Hy-droxy-N'-[(2-oxido-1-naphthyl-κO)methyl-idene]benzohydrazidato-κN',O}dimethyl-tin(IV).

Two independent but very similar mol-ecules comprise the asymmetric unit of the title compound, [Sn(CH(3))(2)(C(18)H(12)N(2)O(3))]. Each Sn atom is coordinated by two methyl groups and two O atoms and an N atom from the dinegative tridentate ligand. The resultant C(2)NO(2) donor set defines a coordination geometry inter-mediate between square-pyramidal and trigonal-pyramidal, with a small tendency towards the former. Zigzag chains running along the a axis mediated by O-H⋯N hydrogen bonding characterize the crystal packing. These are connected into layers in the ab plane by a combination of C-H⋯N and π-π [centroid-centroid distances = 3.658 (2) and 3.6740 (18) Å] inter-actions. The layers are connected along the c axis via C-H⋯O inter-actions.

Related literature

For related studies on organotin compounds, see: Affan et al. (2009 ▶); Zukerman-Schpector et al. (2009 ▶). For the structure of the dichloro­methane solvate of the title compound, see: Cui et al. (2007 ▶). For coordination geometry, see: Addison et al. (1984 ▶).

Experimental

Crystal data

[Sn(CH3)2(C18H12N2O3)]

M = 453.05

Monoclinic,

a = 12.9422 (4) Å

b = 16.5264 (5) Å

c = 16.9949 (5) Å

β = 94.923 (3)°

V = 3621.59 (19) Å3

Z = 8

Mo Kα radiation

μ = 1.43 mm−1

T = 150 K

0.20 × 0.15 × 0.06 mm

Data collection

Oxford Diffraction Gemini E diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.863, T max = 1.000

12413 measured reflections

6668 independent reflections

5647 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.069

S = 1.05

6668 reflections

475 parameters

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.51 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810027078/bt5292sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027078/bt5292Isup2.hkl

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

[Sn(CH3)2(C18H12N2O3)]	F(000) = 1808
Mr = 453.05	Dx = 1.662 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7047 reflections
a = 12.9422 (4) Å	θ = 2.3–27.4°
b = 16.5264 (5) Å	µ = 1.43 mm−1
c = 16.9949 (5) Å	T = 150 K
β = 94.923 (3)°	Prism, pink
V = 3621.59 (19) Å3	0.20 × 0.15 × 0.06 mm
Z = 8

Oxford Diffraction Gemini E diffractometer	6668 independent reflections
Radiation source: fine-focus sealed tube	5647 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 10.5081 pixels mm-1	θmax = 25.5°, θmin = 2.3°
ω scans	h = −15→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −19→19
Tmin = 0.863, Tmax = 1.000	l = −20→19
12413 measured reflections

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0238P)2 + 0.8497P] where P = (Fo2 + 2Fc2)/3
6668 reflections	(Δ/σ)max = 0.001
475 parameters	Δρmax = 0.73 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.372807 (18)	0.439312 (13)	0.384468 (13)	0.01894 (7)
O1	0.22567 (17)	0.48447 (13)	0.33302 (12)	0.0229 (5)
O2	0.51368 (18)	0.37879 (14)	0.38188 (13)	0.0280 (6)
O3	−0.09090 (17)	0.69902 (13)	0.11649 (13)	0.0226 (5)
H3	−0.1239	0.7217	0.1508	0.034*
N1	0.2992 (2)	0.47633 (15)	0.21448 (15)	0.0159 (6)
N2	0.3766 (2)	0.43266 (15)	0.25829 (15)	0.0158 (6)
C1	0.3054 (3)	0.3524 (2)	0.4554 (2)	0.0308 (9)
H1A	0.2763	0.3082	0.4220	0.046*
H1B	0.2502	0.3778	0.4827	0.046*
H1C	0.3585	0.3308	0.4944	0.046*
C2	0.4287 (3)	0.55396 (19)	0.4238 (2)	0.0271 (8)
H2A	0.4204	0.5597	0.4803	0.041*
H2B	0.3893	0.5965	0.3945	0.041*
H2C	0.5022	0.5587	0.4149	0.041*
C3	0.2257 (2)	0.50146 (18)	0.25852 (18)	0.0162 (7)
C4	0.1430 (2)	0.55217 (18)	0.22049 (18)	0.0152 (7)
C5	0.0645 (2)	0.58043 (18)	0.26549 (19)	0.0171 (7)
H5	0.0652	0.5660	0.3196	0.021*
C6	−0.0138 (2)	0.62907 (19)	0.23155 (18)	0.0181 (7)
H6	−0.0666	0.6478	0.2626	0.022*
C7	−0.0163 (2)	0.65090 (19)	0.15242 (19)	0.0181 (7)
C8	0.0604 (2)	0.6219 (2)	0.10710 (19)	0.0215 (8)
H8	0.0593	0.6360	0.0528	0.026*
C9	0.1378 (2)	0.57307 (19)	0.14092 (19)	0.0202 (7)
H9	0.1891	0.5530	0.1092	0.024*
C10	0.4458 (2)	0.39988 (18)	0.21694 (18)	0.0160 (7)
H10	0.4339	0.4055	0.1613	0.019*
C11	0.5367 (2)	0.35692 (18)	0.24451 (19)	0.0169 (7)
C12	0.5666 (3)	0.34850 (19)	0.32603 (19)	0.0190 (7)
C13	0.6590 (3)	0.30561 (18)	0.3504 (2)	0.0224 (8)
H13	0.6788	0.2995	0.4052	0.027*
C14	0.7193 (3)	0.27336 (19)	0.2977 (2)	0.0226 (8)
H14	0.7804	0.2450	0.3162	0.027*
C15	0.6935 (3)	0.28078 (18)	0.2147 (2)	0.0193 (7)
C16	0.7574 (3)	0.24726 (19)	0.1600 (2)	0.0259 (8)
H16	0.8183	0.2187	0.1789	0.031*
C17	0.7338 (3)	0.2550 (2)	0.0806 (2)	0.0334 (9)
H17	0.7775	0.2318	0.0445	0.040*
C18	0.6446 (3)	0.2973 (2)	0.0530 (2)	0.0365 (10)
H18	0.6282	0.3035	−0.0022	0.044*
C19	0.5802 (3)	0.3301 (2)	0.1050 (2)	0.0308 (9)
H19	0.5194	0.3581	0.0849	0.037*
C20	0.6022 (3)	0.32324 (18)	0.18701 (19)	0.0188 (7)
Sn2	0.863063 (17)	0.698292 (13)	0.901481 (13)	0.01777 (7)
O4	0.72509 (17)	0.75323 (13)	0.84463 (12)	0.0234 (5)
O5	0.99479 (18)	0.62575 (14)	0.90442 (13)	0.0291 (6)
O6	0.40545 (17)	0.94156 (14)	0.60703 (13)	0.0240 (5)
H6A	0.3654	0.9612	0.6384	0.036*
N3	0.79687 (19)	0.72937 (15)	0.72772 (15)	0.0150 (6)
N4	0.8715 (2)	0.68727 (14)	0.77582 (15)	0.0150 (6)
C21	0.7751 (3)	0.6187 (2)	0.96517 (19)	0.0261 (8)
H21A	0.7460	0.5760	0.9299	0.039*
H21B	0.7187	0.6486	0.9869	0.039*
H21C	0.8196	0.5944	1.0084	0.039*
C22	0.9403 (3)	0.80532 (19)	0.9414 (2)	0.0290 (9)
H22A	0.9540	0.8034	0.9990	0.043*
H22B	0.8966	0.8523	0.9266	0.043*
H22C	1.0061	0.8099	0.9171	0.043*
C23	0.7252 (2)	0.76115 (18)	0.76921 (19)	0.0167 (7)
C24	0.6415 (2)	0.80870 (17)	0.72659 (18)	0.0151 (7)
C25	0.5548 (2)	0.83069 (18)	0.76511 (19)	0.0166 (7)
H25	0.5506	0.8156	0.8187	0.020*
C26	0.4749 (2)	0.87418 (18)	0.72596 (19)	0.0189 (7)
H26	0.4157	0.8880	0.7526	0.023*
C27	0.4805 (2)	0.89776 (19)	0.64805 (19)	0.0175 (7)
C28	0.5677 (2)	0.8776 (2)	0.60977 (19)	0.0210 (8)
H28	0.5731	0.8950	0.5570	0.025*
C29	0.6457 (2)	0.83292 (19)	0.64771 (19)	0.0196 (7)
H29	0.7037	0.8180	0.6203	0.023*
C30	0.9417 (2)	0.65032 (17)	0.73749 (19)	0.0166 (7)
H30	0.9319	0.6528	0.6815	0.020*
C31	1.0306 (2)	0.60716 (18)	0.76933 (19)	0.0165 (7)
C32	1.0538 (3)	0.59785 (19)	0.8512 (2)	0.0226 (8)
C33	1.1456 (3)	0.55688 (19)	0.8799 (2)	0.0274 (8)
H33	1.1609	0.5505	0.9353	0.033*
C34	1.2119 (3)	0.52668 (19)	0.8300 (2)	0.0278 (9)
H34	1.2737	0.5008	0.8511	0.033*
C35	1.1910 (3)	0.53289 (18)	0.7467 (2)	0.0230 (8)
C36	1.2606 (3)	0.49950 (19)	0.6957 (2)	0.0288 (9)
H36	1.3221	0.4735	0.7171	0.035*
C37	1.2394 (3)	0.5046 (2)	0.6157 (2)	0.0359 (10)
H37	1.2868	0.4824	0.5818	0.043*
C38	1.1497 (3)	0.5418 (2)	0.5836 (2)	0.0361 (10)
H38	1.1354	0.5443	0.5279	0.043*
C39	1.0809 (3)	0.5753 (2)	0.6322 (2)	0.0263 (8)
H39	1.0195	0.6005	0.6092	0.032*
C40	1.0997 (2)	0.57292 (18)	0.7152 (2)	0.0186 (7)

	U11	U22	U33	U12	U13	U23
Sn1	0.02143 (14)	0.02241 (13)	0.01285 (12)	−0.00068 (10)	0.00070 (10)	−0.00022 (10)
O1	0.0201 (13)	0.0329 (13)	0.0160 (12)	0.0038 (11)	0.0031 (10)	0.0017 (11)
O2	0.0300 (14)	0.0385 (14)	0.0150 (12)	0.0083 (12)	−0.0013 (11)	0.0023 (11)
O3	0.0174 (13)	0.0313 (13)	0.0193 (12)	0.0065 (11)	0.0023 (10)	−0.0044 (11)
N1	0.0128 (14)	0.0185 (14)	0.0163 (14)	0.0014 (12)	0.0005 (12)	−0.0022 (12)
N2	0.0137 (14)	0.0180 (14)	0.0151 (14)	−0.0010 (12)	−0.0027 (12)	0.0009 (12)
C1	0.042 (2)	0.032 (2)	0.0191 (19)	−0.0061 (18)	0.0068 (18)	−0.0007 (16)
C2	0.034 (2)	0.0242 (19)	0.0220 (19)	0.0000 (16)	−0.0013 (17)	−0.0006 (16)
C3	0.0127 (17)	0.0159 (16)	0.0196 (18)	−0.0071 (14)	−0.0001 (14)	−0.0061 (14)
C4	0.0114 (16)	0.0177 (16)	0.0163 (17)	−0.0039 (14)	0.0009 (13)	−0.0032 (14)
C5	0.0163 (17)	0.0201 (17)	0.0151 (17)	−0.0038 (14)	0.0022 (14)	−0.0006 (14)
C6	0.0142 (17)	0.0221 (17)	0.0190 (18)	−0.0016 (14)	0.0069 (14)	−0.0031 (15)
C7	0.0105 (17)	0.0215 (18)	0.0218 (18)	0.0012 (14)	−0.0015 (14)	−0.0024 (15)
C8	0.0175 (18)	0.0322 (19)	0.0148 (17)	0.0054 (16)	0.0018 (15)	−0.0033 (15)
C9	0.0146 (17)	0.0258 (18)	0.0206 (18)	0.0014 (15)	0.0033 (15)	−0.0063 (15)
C10	0.0180 (17)	0.0166 (16)	0.0137 (16)	−0.0015 (14)	0.0026 (14)	−0.0018 (14)
C11	0.0172 (18)	0.0144 (16)	0.0186 (17)	−0.0019 (14)	−0.0012 (14)	0.0004 (14)
C12	0.0191 (18)	0.0180 (17)	0.0197 (18)	−0.0006 (14)	0.0008 (15)	0.0003 (14)
C13	0.0223 (19)	0.0219 (18)	0.0219 (18)	−0.0035 (15)	−0.0053 (16)	0.0062 (15)
C14	0.0185 (19)	0.0170 (17)	0.031 (2)	0.0036 (15)	−0.0045 (16)	0.0066 (16)
C15	0.0173 (18)	0.0120 (16)	0.0276 (19)	−0.0004 (14)	−0.0037 (15)	0.0018 (15)
C16	0.0186 (19)	0.0184 (18)	0.040 (2)	0.0060 (15)	0.0003 (17)	−0.0025 (17)
C17	0.032 (2)	0.035 (2)	0.034 (2)	0.0126 (18)	0.0064 (19)	−0.0082 (18)
C18	0.041 (2)	0.050 (2)	0.0190 (19)	0.019 (2)	0.0012 (18)	−0.0046 (18)
C19	0.026 (2)	0.042 (2)	0.024 (2)	0.0161 (18)	−0.0010 (17)	−0.0065 (18)
C20	0.0185 (18)	0.0159 (17)	0.0213 (18)	−0.0012 (14)	−0.0020 (15)	−0.0028 (14)
Sn2	0.01788 (13)	0.02101 (13)	0.01475 (12)	0.00164 (10)	0.00322 (10)	0.00117 (10)
O4	0.0200 (13)	0.0354 (14)	0.0157 (12)	0.0102 (11)	0.0067 (10)	0.0035 (11)
O5	0.0279 (14)	0.0394 (14)	0.0200 (13)	0.0163 (12)	0.0025 (11)	0.0036 (11)
O6	0.0190 (13)	0.0342 (14)	0.0188 (12)	0.0109 (11)	0.0010 (10)	−0.0031 (11)
N3	0.0095 (14)	0.0184 (14)	0.0172 (14)	0.0025 (11)	0.0012 (11)	0.0008 (12)
N4	0.0137 (14)	0.0156 (13)	0.0157 (14)	0.0007 (11)	0.0016 (12)	0.0026 (11)
C21	0.036 (2)	0.0276 (19)	0.0147 (18)	−0.0106 (17)	0.0039 (16)	−0.0008 (15)
C22	0.028 (2)	0.028 (2)	0.031 (2)	−0.0085 (17)	0.0023 (18)	−0.0017 (17)
C23	0.0131 (17)	0.0148 (16)	0.0232 (18)	−0.0054 (14)	0.0072 (15)	−0.0013 (14)
C24	0.0144 (17)	0.0118 (15)	0.0195 (17)	−0.0017 (13)	0.0037 (14)	−0.0022 (14)
C25	0.0155 (17)	0.0162 (16)	0.0186 (17)	−0.0018 (14)	0.0035 (14)	−0.0024 (14)
C26	0.0133 (17)	0.0179 (17)	0.0263 (19)	−0.0028 (14)	0.0071 (15)	−0.0053 (15)
C27	0.0112 (17)	0.0197 (17)	0.0211 (18)	−0.0016 (14)	−0.0022 (14)	−0.0044 (15)
C28	0.0192 (18)	0.0302 (19)	0.0139 (17)	0.0025 (16)	0.0024 (14)	0.0002 (15)
C29	0.0140 (17)	0.0231 (17)	0.0225 (18)	0.0042 (15)	0.0067 (15)	−0.0061 (15)
C30	0.0188 (18)	0.0137 (16)	0.0180 (17)	−0.0041 (14)	0.0048 (15)	−0.0020 (14)
C31	0.0101 (16)	0.0165 (17)	0.0233 (18)	−0.0013 (13)	0.0038 (14)	−0.0008 (14)
C32	0.0220 (19)	0.0182 (17)	0.028 (2)	0.0012 (15)	0.0057 (16)	0.0027 (16)
C33	0.026 (2)	0.027 (2)	0.029 (2)	0.0046 (16)	−0.0004 (17)	0.0086 (17)
C34	0.021 (2)	0.0175 (17)	0.045 (2)	0.0058 (15)	0.0026 (18)	0.0093 (17)
C35	0.0171 (18)	0.0103 (16)	0.042 (2)	−0.0036 (14)	0.0062 (17)	0.0002 (16)
C36	0.019 (2)	0.0135 (17)	0.055 (3)	0.0025 (15)	0.0099 (19)	−0.0043 (18)
C37	0.030 (2)	0.028 (2)	0.053 (3)	0.0003 (18)	0.021 (2)	−0.018 (2)
C38	0.034 (2)	0.040 (2)	0.036 (2)	0.0026 (19)	0.012 (2)	−0.0114 (19)
C39	0.0194 (19)	0.0294 (19)	0.031 (2)	0.0020 (16)	0.0087 (17)	−0.0072 (17)
C40	0.0141 (17)	0.0136 (16)	0.0286 (19)	−0.0001 (14)	0.0051 (15)	−0.0024 (15)

Sn1—O2	2.083 (2)	Sn2—O5	2.081 (2)
Sn1—C1	2.112 (3)	Sn2—C21	2.099 (3)
Sn1—C2	2.116 (3)	Sn2—C22	2.115 (3)
Sn1—N2	2.152 (2)	Sn2—N4	2.155 (2)
Sn1—O1	2.159 (2)	Sn2—O4	2.157 (2)
O1—C3	1.297 (4)	O4—C23	1.288 (4)
O2—C12	1.316 (4)	O5—C32	1.316 (4)
O3—C7	1.355 (4)	O6—C27	1.355 (4)
O3—H3	0.8400	O6—H6A	0.8400
N1—C3	1.326 (4)	N3—C23	1.321 (4)
N1—N2	1.397 (3)	N3—N4	1.396 (3)
N2—C10	1.303 (4)	N4—C30	1.314 (4)
C1—H1A	0.9800	C21—H21A	0.9800
C1—H1B	0.9800	C21—H21B	0.9800
C1—H1C	0.9800	C21—H21C	0.9800
C2—H2A	0.9800	C22—H22A	0.9800
C2—H2B	0.9800	C22—H22B	0.9800
C2—H2C	0.9800	C22—H22C	0.9800
C3—C4	1.466 (4)	C23—C24	1.477 (4)
C4—C9	1.392 (4)	C24—C25	1.395 (4)
C4—C5	1.403 (4)	C24—C29	1.405 (4)
C5—C6	1.380 (4)	C25—C26	1.382 (4)
C5—H5	0.9500	C25—H25	0.9500
C6—C7	1.390 (4)	C26—C27	1.388 (4)
C6—H6	0.9500	C26—H26	0.9500
C7—C8	1.393 (4)	C27—C28	1.390 (4)
C8—C9	1.373 (4)	C28—C29	1.367 (4)
C8—H8	0.9500	C28—H28	0.9500
C9—H9	0.9500	C29—H29	0.9500
C10—C11	1.418 (4)	C30—C31	1.421 (4)
C10—H10	0.9500	C30—H30	0.9500
C11—C12	1.413 (4)	C31—C32	1.407 (5)
C11—C20	1.458 (4)	C31—C40	1.452 (4)
C12—C13	1.421 (4)	C32—C33	1.417 (5)
C13—C14	1.347 (4)	C33—C34	1.352 (4)
C13—H13	0.9500	C33—H33	0.9500
C14—C15	1.427 (4)	C34—C35	1.423 (5)
C14—H14	0.9500	C34—H34	0.9500
C15—C16	1.409 (4)	C35—C36	1.415 (4)
C15—C20	1.419 (4)	C35—C40	1.418 (5)
C16—C17	1.364 (5)	C36—C37	1.365 (5)
C16—H16	0.9500	C36—H36	0.9500
C17—C18	1.395 (5)	C37—C38	1.384 (5)
C17—H17	0.9500	C37—H37	0.9500
C18—C19	1.377 (5)	C38—C39	1.381 (5)
C18—H18	0.9500	C38—H38	0.9500
C19—C20	1.402 (5)	C39—C40	1.410 (5)
C19—H19	0.9500	C39—H39	0.9500
O2—Sn1—C1	95.19 (12)	O5—Sn2—C21	96.08 (12)
O2—Sn1—C2	99.24 (12)	O5—Sn2—C22	96.34 (12)
C1—Sn1—C2	125.14 (13)	C21—Sn2—C22	128.37 (13)
O2—Sn1—N2	81.92 (9)	O5—Sn2—N4	82.19 (9)
C1—Sn1—N2	125.45 (11)	C21—Sn2—N4	122.25 (11)
C2—Sn1—N2	108.92 (11)	C22—Sn2—N4	109.01 (12)
O2—Sn1—O1	154.21 (8)	O5—Sn2—O4	153.95 (9)
C1—Sn1—O1	94.20 (12)	C21—Sn2—O4	91.72 (12)
C2—Sn1—O1	94.83 (11)	C22—Sn2—O4	98.16 (12)
N2—Sn1—O1	73.08 (9)	N4—Sn2—O4	72.67 (9)
C3—O1—Sn1	113.32 (19)	C23—O4—Sn2	114.62 (19)
C12—O2—Sn1	135.1 (2)	C32—O5—Sn2	135.1 (2)
C7—O3—H3	109.5	C27—O6—H6A	109.5
C3—N1—N2	112.2 (3)	C23—N3—N4	111.6 (2)
C10—N2—N1	115.0 (3)	C30—N4—N3	114.5 (3)
C10—N2—Sn1	129.4 (2)	C30—N4—Sn2	128.8 (2)
N1—N2—Sn1	115.33 (17)	N3—N4—Sn2	116.53 (17)
Sn1—C1—H1A	109.5	Sn2—C21—H21A	109.5
Sn1—C1—H1B	109.5	Sn2—C21—H21B	109.5
H1A—C1—H1B	109.5	H21A—C21—H21B	109.5
Sn1—C1—H1C	109.5	Sn2—C21—H21C	109.5
H1A—C1—H1C	109.5	H21A—C21—H21C	109.5
H1B—C1—H1C	109.5	H21B—C21—H21C	109.5
Sn1—C2—H2A	109.5	Sn2—C22—H22A	109.5
Sn1—C2—H2B	109.5	Sn2—C22—H22B	109.5
H2A—C2—H2B	109.5	H22A—C22—H22B	109.5
Sn1—C2—H2C	109.5	Sn2—C22—H22C	109.5
H2A—C2—H2C	109.5	H22A—C22—H22C	109.5
H2B—C2—H2C	109.5	H22B—C22—H22C	109.5
O1—C3—N1	122.9 (3)	O4—C23—N3	123.5 (3)
O1—C3—C4	119.5 (3)	O4—C23—C24	118.6 (3)
N1—C3—C4	117.5 (3)	N3—C23—C24	118.0 (3)
C9—C4—C5	118.1 (3)	C25—C24—C29	118.2 (3)
C9—C4—C3	122.9 (3)	C25—C24—C23	119.6 (3)
C5—C4—C3	119.1 (3)	C29—C24—C23	122.2 (3)
C6—C5—C4	120.4 (3)	C26—C25—C24	120.6 (3)
C6—C5—H5	119.8	C26—C25—H25	119.7
C4—C5—H5	119.8	C24—C25—H25	119.7
C5—C6—C7	120.7 (3)	C25—C26—C27	120.5 (3)
C5—C6—H6	119.7	C25—C26—H26	119.8
C7—C6—H6	119.7	C27—C26—H26	119.8
O3—C7—C6	123.0 (3)	O6—C27—C26	123.1 (3)
O3—C7—C8	117.8 (3)	O6—C27—C28	117.5 (3)
C6—C7—C8	119.2 (3)	C26—C27—C28	119.3 (3)
C9—C8—C7	120.0 (3)	C29—C28—C27	120.3 (3)
C9—C8—H8	120.0	C29—C28—H28	119.8
C7—C8—H8	120.0	C27—C28—H28	119.8
C8—C9—C4	121.7 (3)	C28—C29—C24	121.1 (3)
C8—C9—H9	119.2	C28—C29—H29	119.4
C4—C9—H9	119.2	C24—C29—H29	119.4
N2—C10—C11	128.2 (3)	N4—C30—C31	128.1 (3)
N2—C10—H10	115.9	N4—C30—H30	116.0
C11—C10—H10	115.9	C31—C30—H30	116.0
C12—C11—C10	121.5 (3)	C32—C31—C30	121.9 (3)
C12—C11—C20	119.5 (3)	C32—C31—C40	119.6 (3)
C10—C11—C20	118.9 (3)	C30—C31—C40	118.5 (3)
O2—C12—C11	123.6 (3)	O5—C32—C31	123.6 (3)
O2—C12—C13	117.2 (3)	O5—C32—C33	116.7 (3)
C11—C12—C13	119.2 (3)	C31—C32—C33	119.6 (3)
C14—C13—C12	121.7 (3)	C34—C33—C32	121.2 (3)
C14—C13—H13	119.2	C34—C33—H33	119.4
C12—C13—H13	119.2	C32—C33—H33	119.4
C13—C14—C15	121.6 (3)	C33—C34—C35	121.4 (3)
C13—C14—H14	119.2	C33—C34—H34	119.3
C15—C14—H14	119.2	C35—C34—H34	119.3
C16—C15—C20	119.7 (3)	C36—C35—C40	120.3 (3)
C16—C15—C14	121.1 (3)	C36—C35—C34	120.3 (3)
C20—C15—C14	119.1 (3)	C40—C35—C34	119.4 (3)
C17—C16—C15	121.4 (3)	C37—C36—C35	120.1 (4)
C17—C16—H16	119.3	C37—C36—H36	119.9
C15—C16—H16	119.3	C35—C36—H36	119.9
C16—C17—C18	119.2 (3)	C36—C37—C38	120.6 (3)
C16—C17—H17	120.4	C36—C37—H37	119.7
C18—C17—H17	120.4	C38—C37—H37	119.7
C19—C18—C17	120.7 (3)	C39—C38—C37	120.3 (4)
C19—C18—H18	119.7	C39—C38—H38	119.8
C17—C18—H18	119.7	C37—C38—H38	119.8
C18—C19—C20	121.5 (3)	C38—C39—C40	121.4 (4)
C18—C19—H19	119.2	C38—C39—H39	119.3
C20—C19—H19	119.2	C40—C39—H39	119.3
C19—C20—C15	117.5 (3)	C39—C40—C35	117.2 (3)
C19—C20—C11	123.7 (3)	C39—C40—C31	124.1 (3)
C15—C20—C11	118.8 (3)	C35—C40—C31	118.7 (3)
O2—Sn1—O1—C3	−29.7 (3)	O5—Sn2—O4—C23	−24.6 (3)
C1—Sn1—O1—C3	−140.9 (2)	C21—Sn2—O4—C23	−132.3 (2)
C2—Sn1—O1—C3	93.3 (2)	C22—Sn2—O4—C23	98.6 (2)
N2—Sn1—O1—C3	−15.0 (2)	N4—Sn2—O4—C23	−8.9 (2)
C1—Sn1—O2—C12	120.3 (3)	C21—Sn2—O5—C32	128.0 (3)
C2—Sn1—O2—C12	−112.8 (3)	C22—Sn2—O5—C32	−102.2 (3)
N2—Sn1—O2—C12	−4.8 (3)	N4—Sn2—O5—C32	6.2 (3)
O1—Sn1—O2—C12	9.4 (4)	O4—Sn2—O5—C32	21.3 (4)
C3—N1—N2—C10	173.8 (3)	C23—N3—N4—C30	176.3 (2)
C3—N1—N2—Sn1	−12.0 (3)	C23—N3—N4—Sn2	−7.9 (3)
O2—Sn1—N2—C10	1.2 (3)	O5—Sn2—N4—C30	−2.8 (2)
C1—Sn1—N2—C10	−89.4 (3)	C21—Sn2—N4—C30	−95.1 (3)
C2—Sn1—N2—C10	98.3 (3)	C22—Sn2—N4—C30	91.2 (3)
O1—Sn1—N2—C10	−172.4 (3)	O4—Sn2—N4—C30	−175.9 (3)
O2—Sn1—N2—N1	−172.0 (2)	O5—Sn2—N4—N3	−177.9 (2)
C1—Sn1—N2—N1	97.4 (2)	C21—Sn2—N4—N3	89.8 (2)
C2—Sn1—N2—N1	−74.9 (2)	C22—Sn2—N4—N3	−83.9 (2)
O1—Sn1—N2—N1	14.45 (18)	O4—Sn2—N4—N3	8.99 (19)
Sn1—O1—C3—N1	14.9 (4)	Sn2—O4—C23—N3	8.4 (4)
Sn1—O1—C3—C4	−163.7 (2)	Sn2—O4—C23—C24	−171.2 (2)
N2—N1—C3—O1	−2.1 (4)	N4—N3—C23—O4	−0.4 (4)
N2—N1—C3—C4	176.5 (2)	N4—N3—C23—C24	179.1 (2)
O1—C3—C4—C9	179.9 (3)	O4—C23—C24—C25	−12.1 (4)
N1—C3—C4—C9	1.3 (5)	N3—C23—C24—C25	168.4 (3)
O1—C3—C4—C5	−0.8 (4)	O4—C23—C24—C29	168.0 (3)
N1—C3—C4—C5	−179.4 (3)	N3—C23—C24—C29	−11.5 (4)
C9—C4—C5—C6	−1.5 (5)	C29—C24—C25—C26	0.8 (5)
C3—C4—C5—C6	179.3 (3)	C23—C24—C25—C26	−179.1 (3)
C4—C5—C6—C7	0.0 (5)	C24—C25—C26—C27	−1.0 (5)
C5—C6—C7—O3	−179.4 (3)	C25—C26—C27—O6	−178.9 (3)
C5—C6—C7—C8	1.1 (5)	C25—C26—C27—C28	−0.4 (5)
O3—C7—C8—C9	179.9 (3)	O6—C27—C28—C29	−179.4 (3)
C6—C7—C8—C9	−0.6 (5)	C26—C27—C28—C29	2.0 (5)
C7—C8—C9—C4	−0.9 (5)	C27—C28—C29—C24	−2.2 (5)
C5—C4—C9—C8	2.0 (5)	C25—C24—C29—C28	0.8 (5)
C3—C4—C9—C8	−178.8 (3)	C23—C24—C29—C28	−179.3 (3)
N1—N2—C10—C11	175.5 (3)	N3—N4—C30—C31	175.7 (3)
Sn1—N2—C10—C11	2.3 (5)	Sn2—N4—C30—C31	0.6 (5)
N2—C10—C11—C12	−3.8 (5)	N4—C30—C31—C32	0.9 (5)
N2—C10—C11—C20	178.3 (3)	N4—C30—C31—C40	−178.2 (3)
Sn1—O2—C12—C11	4.8 (5)	Sn2—O5—C32—C31	−6.8 (5)
Sn1—O2—C12—C13	−175.5 (2)	Sn2—O5—C32—C33	172.8 (2)
C10—C11—C12—O2	0.3 (5)	C30—C31—C32—O5	2.0 (5)
C20—C11—C12—O2	178.2 (3)	C40—C31—C32—O5	−178.9 (3)
C10—C11—C12—C13	−179.3 (3)	C30—C31—C32—C33	−177.6 (3)
C20—C11—C12—C13	−1.5 (4)	C40—C31—C32—C33	1.5 (5)
O2—C12—C13—C14	−179.1 (3)	O5—C32—C33—C34	−179.4 (3)
C11—C12—C13—C14	0.6 (5)	C31—C32—C33—C34	0.3 (5)
C12—C13—C14—C15	0.1 (5)	C32—C33—C34—C35	−1.6 (5)
C13—C14—C15—C16	179.6 (3)	C33—C34—C35—C36	−178.8 (3)
C13—C14—C15—C20	0.1 (5)	C33—C34—C35—C40	1.2 (5)
C20—C15—C16—C17	0.3 (5)	C40—C35—C36—C37	−1.0 (5)
C14—C15—C16—C17	−179.2 (3)	C34—C35—C36—C37	179.1 (3)
C15—C16—C17—C18	0.3 (6)	C35—C36—C37—C38	−0.4 (5)
C16—C17—C18—C19	−0.8 (6)	C36—C37—C38—C39	0.8 (6)
C17—C18—C19—C20	0.8 (6)	C37—C38—C39—C40	0.2 (6)
C18—C19—C20—C15	−0.2 (5)	C38—C39—C40—C35	−1.6 (5)
C18—C19—C20—C11	179.9 (3)	C38—C39—C40—C31	179.8 (3)
C16—C15—C20—C19	−0.3 (5)	C36—C35—C40—C39	1.9 (5)
C14—C15—C20—C19	179.2 (3)	C34—C35—C40—C39	−178.1 (3)
C16—C15—C20—C11	179.5 (3)	C36—C35—C40—C31	−179.4 (3)
C14—C15—C20—C11	−0.9 (4)	C34—C35—C40—C31	0.6 (4)
C12—C11—C20—C19	−178.5 (3)	C32—C31—C40—C39	176.7 (3)
C10—C11—C20—C19	−0.6 (5)	C30—C31—C40—C39	−4.2 (5)
C12—C11—C20—C15	1.6 (4)	C32—C31—C40—C35	−1.9 (4)
C10—C11—C20—C15	179.5 (3)	C30—C31—C40—C35	177.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N3i	0.84	1.91	2.749 (3)	178
O6—H6a···N1ii	0.84	1.91	2.738 (3)	167
C8—H8···O5iii	0.95	2.59	3.477 (4)	155
C21—H21a···N1iv	0.98	2.62	3.494 (4)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N3i	0.84	1.91	2.749 (3)	178
O6—H6a⋯N1ii	0.84	1.91	2.738 (3)	167
C8—H8⋯O5iii	0.95	2.59	3.477 (4)	155
C21—H21a⋯N1iv	0.98	2.62	3.494 (4)	149

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