catena-Poly[[triphenyl­tin(IV)]-μ-2,4-dinitro­benzoato]

In the title compound, [Sn (C₂₅H₁₈N₂O₆)]_n, the Sn atom shows a trigonal bipyramidal coordination with equatorial phenyl groups and axial carboxylates linking the metal atoms into a polymeric chain. The nitro groups are slightly twisted away from the attached aromatic ring. In the crystal structure, the chains are linked by inter­molecular C—H...O inter­actions, forming columns along the b axis. In addition, the crystal structure is further stabilized by inter­molecular π–π inter­actions, with centroid-to-centroid distance of 3.5538 (15) Å.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.038
• wR factor = 0.120
• Data-to-parameter ratio = 33.3

checkCIF/PLATON results

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Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.65 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Besides their significant industrial applications (Willem et al., 1997; Novelli et al., 1999; Gielen et al., 2000), organotin (IV) complexes are reported to exhibit antimicrobial and antitumour properties. Generally triphenyltin(IV) carboxylate complexes exist as monomeric structures with four-coordinate distorted tetrahedal or five-coordinate trigonal bypyramid geometries (Baul et al., 2001; Yeap & Teoh, 2003; Win et al., 2006). Recently, (3,5-dintrobenzoato)triphenyltin(IV) is reported to existed as a monomeric structure with four-coordinate distorted tetrahedral geometry (Win et al., 2006). Both the nitro groups are substituted at ortho and para positions of the benzene rings in (2,4-dinitrobenzoato)triphenyl(IV) complex whereas the dinitro groups occupy the meta position in (3,5-dinitrobenzoato)triphenyltin(IV) complex. In the crystal structure, the title molecules form polymeric chains along the a axis. As such, the complex obtained in this study exist as a polymeric structure with a five-coordinate trigonal bypyramid geometry (Scheme). The Sn coordination is a distorted trigonal bipyramid (scheme and Table 1). Bond lengths and angles in (I) (Figure 1) have normal values (Allen et al., 1987) and agree well with those found in related structures (Win et al., 2007). The nitro groups at C23 and C25 are slightly twisted away from attached benzene rings with torsion angle O3—N1—C25—C20 = -14.2 (3)°, and O5—N2—C23—C22 = -16.7 (4)°, respectively.

The intramolecular C8—H8A···O1 and C18—H18A···O1 interactions (Table 1 and figure 1) generate S(5) ring motifs (Bernstein et al., 1995). In the crystal structure, the molecules linked by intermolecular C17—H17A···O6, C21—H21A···O5, C12—H12A···O2 and C14—H14A···O2 interactions to form columns along the b axis (Figure 2). In addition, the crystal packing is further stabilized by the weak intermolecular π-π interactions involving the C1—C6 ring (centroid Cg1) and the C20—C25 (centroid Cg2) benzene rings with a Cg1···Cg2^iv distance of 3.5538 (15)Å [symmetry code: iv (1 + x, y, z)].

Related literature

For literature on hydrogen-bond motifs, see Bernstein et al. (1995). For data on bond lengths and angles, see Allen et al. (1987). For related literature, see: Baul et al. (2001); Gielen et al. (2000); Novelli et al. (1999); Willem et al. (1997); Win et al. (2006); Win et al. (2007); Yeap & Teoh (2003).

S2. Experimental

The complex (2,4-dinitrobenzoato)diphenyltin(IV) was obtained by heating under reflux a 1:1 molar mixture of triphenyltin(IV) hydroxide (1.10 g, 3 mmole) and 2,4-dinitrobenzoic acid (0.64 g, 3 mmole) in ethanol (50 ml) for two hours. A clear yellowish solution was isolated by filtration and kept in a bottle. After two weeks, some yellowish precipitate (1.38 g, 82.3% yield) were obtained which are then recrystallized. Melting point: 160.4 - 161.2°C. Analysis found for C₂₅H₁₈N₂O₆Sn: C, 53.31; H, 3.00; N, 4.91; Sn. 21.03%; calculated for C₂₅H₁₈N₂O₆Sn: C, 53.51; H, 3.23; N, 5.00; Sn, 21.15%. FTIR as KBr disc (cm^-1): v(C—H) aromatic 3069, 3051, 3023; v(COO)_as 1599, v(COO)_s 1345, v(NO₂) 1541, v(Sn—O) 453. ¹H-NMR: δ: phenyl protons 7.47 - 7.50 (9H, m); 7.75 - 7.78 (6H, m); benzene 7.90 - 7.92 (1H, d, J = 8.4 Hz); 8.35 - 8.38 (1H, dd, J = 8.4 Hz); 8.60 - 8.61 (1H, d, 2.1 Hz)p.p.m.. ¹³C-NMR: δ:phenyl carbons C_ipso 137.68 (655.6 Hz), C_ortho 137.27 (48.9 Hz), C_meta 129,66 (65.1 Hz), C_para 131.17 (13.1 Hz); benzene 119.58, 127.26, 132.21, 134.58, 148,73, 148.97; COO 168.56 p.p.m.. ¹¹⁹Sn-NMR: δ: -81.04 p.p.m..

S3. Refinement

The H atoms were positional geometrically and treated as riding, with C—H = 0.93Å and U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Figures

	Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering. The dashed lines indicate intramolecular hydrogen bonds.
	Fig. 2. The crystal packing of (I), viewed down the a axis. The intermolecular C—H···O hydrogen bonds are shown as dashed lines.

catena-Poly[[triphenyltin(IV)]-µ-2,4-dinitrobenzoato]

Crystal data

[Sn(C25H18N2O6)]	F(000) = 1120
Mr = 561.10	Dx = 1.661 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5968 reflections
a = 6.5835 (1) Å	θ = 1.4–35.6°
b = 11.8399 (2) Å	µ = 1.18 mm^−1
c = 29.0173 (4) Å	T = 100 K
β = 97.317 (1)°	Block, colourless
V = 2243.42 (6) Å^3	0.27 × 0.14 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEXII CCD area-detector diffractometer	10230 independent reflections
Radiation source: fine-focus sealed tube	8104 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 8.33 pixels mm^-1	θmax = 35.6°, θmin = 1.4°
ω scans	h = −10→9
Absorption correction: multi-scan SADABS (Bruker, 2005)	k = −19→18
Tmin = 0.813, Tmax = 0.887	l = −47→47
45670 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0546P)^2 + 2.2536P] where P = (Fo^2 + 2Fc^2)/3
10230 reflections	(Δ/σ)max < 0.001
307 parameters	Δρmax = 0.77 e Å^−3
0 restraints	Δρmin = −0.87 e Å^−3

Special details

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Sn1	0.87124 (2)	0.294273 (13)	0.087817 (5)	0.01171 (5)
O1	0.5266 (3)	0.29990 (15)	0.07927 (7)	0.0159 (3)
O2	0.2108 (3)	0.31893 (15)	0.09542 (7)	0.0163 (3)
O3	0.2851 (3)	0.11530 (17)	0.03396 (6)	0.0215 (4)
O4	0.3619 (4)	−0.06212 (18)	0.04299 (7)	0.0272 (4)
O5	0.5299 (4)	−0.1099 (2)	0.25504 (9)	0.0421 (6)
O6	0.3845 (4)	−0.21551 (18)	0.19930 (9)	0.0334 (5)
N1	0.3405 (3)	0.03299 (19)	0.05774 (7)	0.0160 (4)
N2	0.4504 (4)	−0.1246 (2)	0.21479 (9)	0.0243 (5)
C1	0.8850 (4)	0.1206 (2)	0.10719 (8)	0.0140 (4)
C2	0.9165 (4)	0.0846 (2)	0.15348 (8)	0.0147 (4)
H2A	0.9314	0.1375	0.1773	0.018*
C3	0.9257 (4)	−0.0307 (2)	0.16399 (9)	0.0182 (4)
H3A	0.9486	−0.0540	0.1948	0.022*
C4	0.9008 (4)	−0.1108 (2)	0.12863 (10)	0.0205 (5)
H4A	0.9063	−0.1874	0.1358	0.025*
C5	0.8678 (4)	−0.0763 (2)	0.08267 (9)	0.0185 (5)
H5A	0.8503	−0.1297	0.0590	0.022*
C6	0.8607 (4)	0.0389 (2)	0.07174 (9)	0.0164 (4)
H6A	0.8397	0.0616	0.0408	0.020*
C7	0.8551 (4)	0.3266 (2)	0.01530 (8)	0.0161 (4)
C8	0.6708 (4)	0.3126 (2)	−0.01376 (9)	0.0200 (5)
H8A	0.5534	0.2914	−0.0012	0.024*
C9	0.6616 (5)	0.3300 (3)	−0.06136 (10)	0.0280 (6)
H9A	0.5379	0.3210	−0.0804	0.034*
C10	0.8351 (6)	0.3608 (3)	−0.08061 (10)	0.0302 (7)
H10A	0.8285	0.3725	−0.1125	0.036*
C11	1.0176 (5)	0.3741 (3)	−0.05225 (10)	0.0279 (6)
H11A	1.1344	0.3947	−0.0651	0.034*
C12	1.0296 (4)	0.3571 (2)	−0.00454 (10)	0.0206 (5)
H12A	1.1541	0.3661	0.0142	0.025*
C13	0.8637 (3)	0.4209 (2)	0.14002 (8)	0.0142 (4)
C14	1.0354 (4)	0.4420 (2)	0.17288 (9)	0.0216 (5)
H14A	1.1514	0.3970	0.1734	0.026*
C15	1.0334 (5)	0.5301 (3)	0.20481 (10)	0.0262 (6)
H15A	1.1481	0.5430	0.2264	0.031*
C16	0.8629 (5)	0.5983 (3)	0.20472 (10)	0.0258 (6)
H16A	0.8633	0.6578	0.2257	0.031*
C17	0.6903 (5)	0.5767 (3)	0.17276 (10)	0.0250 (5)
H17A	0.5739	0.6213	0.1728	0.030*
C18	0.6912 (4)	0.4891 (2)	0.14096 (9)	0.0189 (5)
H18A	0.5749	0.4757	0.1199	0.023*
C19	0.3747 (3)	0.2646 (2)	0.09720 (8)	0.0126 (4)
C20	0.3959 (3)	0.1593 (2)	0.12628 (8)	0.0135 (4)
C21	0.4358 (4)	0.1730 (2)	0.17424 (9)	0.0159 (4)
H21A	0.4489	0.2454	0.1867	0.019*
C22	0.4562 (4)	0.0801 (2)	0.20357 (8)	0.0180 (5)
H22A	0.4843	0.0891	0.2356	0.022*
C23	0.4338 (4)	−0.0263 (2)	0.18396 (9)	0.0172 (4)
C24	0.3965 (4)	−0.0443 (2)	0.13664 (9)	0.0161 (4)
H24A	0.3840	−0.1168	0.1242	0.019*
C25	0.3789 (3)	0.0502 (2)	0.10870 (8)	0.0131 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.00987 (7)	0.01279 (7)	0.01270 (7)	0.00097 (5)	0.00238 (5)	0.00141 (5)
O1	0.0082 (7)	0.0209 (8)	0.0193 (8)	0.0007 (6)	0.0048 (6)	0.0025 (7)
O2	0.0104 (7)	0.0169 (8)	0.0226 (9)	0.0018 (6)	0.0059 (6)	−0.0001 (7)
O3	0.0290 (10)	0.0208 (9)	0.0139 (8)	0.0013 (8)	0.0001 (7)	0.0011 (7)
O4	0.0394 (12)	0.0199 (9)	0.0217 (10)	0.0019 (9)	0.0019 (8)	−0.0077 (8)
O5	0.0514 (16)	0.0440 (15)	0.0275 (12)	−0.0072 (12)	−0.0085 (11)	0.0198 (11)
O6	0.0495 (15)	0.0187 (10)	0.0337 (12)	0.0065 (10)	0.0122 (11)	0.0075 (9)
N1	0.0125 (8)	0.0193 (10)	0.0165 (9)	0.0006 (7)	0.0035 (7)	−0.0025 (7)
N2	0.0239 (11)	0.0236 (11)	0.0262 (12)	0.0059 (9)	0.0065 (9)	0.0105 (9)
C1	0.0140 (9)	0.0137 (9)	0.0141 (10)	0.0017 (8)	0.0013 (7)	0.0000 (8)
C2	0.0148 (10)	0.0161 (10)	0.0131 (9)	0.0010 (8)	0.0013 (7)	0.0001 (8)
C3	0.0176 (10)	0.0193 (11)	0.0178 (11)	0.0022 (9)	0.0029 (8)	0.0058 (9)
C4	0.0228 (12)	0.0127 (10)	0.0260 (13)	0.0013 (9)	0.0033 (10)	0.0040 (9)
C5	0.0188 (11)	0.0164 (11)	0.0210 (12)	−0.0010 (9)	0.0054 (9)	−0.0034 (9)
C6	0.0177 (10)	0.0178 (11)	0.0140 (10)	0.0000 (8)	0.0024 (8)	−0.0005 (8)
C7	0.0223 (11)	0.0144 (10)	0.0125 (9)	0.0016 (9)	0.0053 (8)	0.0016 (8)
C8	0.0195 (11)	0.0228 (12)	0.0176 (11)	0.0028 (9)	0.0017 (9)	0.0014 (9)
C9	0.0388 (17)	0.0268 (14)	0.0169 (12)	0.0035 (13)	−0.0024 (11)	0.0021 (10)
C10	0.055 (2)	0.0230 (13)	0.0135 (11)	0.0108 (13)	0.0079 (12)	0.0050 (10)
C11	0.0412 (17)	0.0230 (13)	0.0232 (13)	0.0080 (12)	0.0178 (12)	0.0075 (10)
C12	0.0255 (12)	0.0177 (11)	0.0202 (12)	0.0017 (10)	0.0086 (9)	0.0045 (9)
C13	0.0115 (9)	0.0162 (10)	0.0156 (10)	0.0004 (8)	0.0050 (7)	0.0020 (8)
C14	0.0221 (12)	0.0254 (13)	0.0170 (11)	0.0004 (10)	0.0015 (9)	−0.0049 (9)
C15	0.0318 (15)	0.0299 (14)	0.0166 (11)	−0.0044 (12)	0.0021 (10)	−0.0060 (10)
C16	0.0315 (15)	0.0254 (14)	0.0218 (13)	−0.0005 (11)	0.0084 (11)	−0.0063 (10)
C17	0.0306 (14)	0.0220 (13)	0.0236 (13)	0.0078 (11)	0.0076 (11)	−0.0014 (10)
C18	0.0223 (12)	0.0175 (11)	0.0176 (11)	0.0041 (9)	0.0049 (9)	−0.0010 (9)
C19	0.0104 (9)	0.0134 (9)	0.0137 (9)	−0.0013 (7)	0.0004 (7)	−0.0010 (7)
C20	0.0111 (9)	0.0160 (10)	0.0132 (9)	0.0007 (8)	0.0007 (7)	−0.0003 (8)
C21	0.0144 (10)	0.0176 (10)	0.0155 (10)	0.0006 (8)	0.0010 (8)	−0.0021 (8)
C22	0.0157 (10)	0.0271 (12)	0.0112 (9)	0.0029 (9)	0.0013 (8)	0.0016 (9)
C23	0.0139 (10)	0.0191 (11)	0.0189 (11)	0.0039 (8)	0.0037 (8)	0.0049 (9)
C24	0.0138 (9)	0.0167 (10)	0.0183 (10)	0.0020 (8)	0.0037 (8)	0.0014 (8)
C25	0.0105 (9)	0.0161 (10)	0.0132 (9)	0.0004 (7)	0.0030 (7)	−0.0010 (8)

Geometric parameters (Å, º)

Sn1—C7	2.128 (2)	C9—C10	1.383 (5)
Sn1—C1	2.130 (2)	C9—H9A	0.9300
Sn1—C13	2.136 (2)	C10—C11	1.376 (5)
Sn1—O2^i	2.2370 (18)	C10—H10A	0.9300
Sn1—O1	2.2517 (17)	C11—C12	1.391 (4)
O1—C19	1.257 (3)	C11—H11A	0.9300
O2—C19	1.252 (3)	C12—H12A	0.9300
O2—Sn1^ii	2.2370 (18)	C13—C18	1.397 (3)
O3—N1	1.223 (3)	C13—C14	1.405 (3)
O4—N1	1.219 (3)	C14—C15	1.396 (4)
O5—N2	1.230 (3)	C14—H14A	0.9300
O6—N2	1.224 (3)	C15—C16	1.383 (4)
N1—C25	1.482 (3)	C15—H15A	0.9300
N2—C23	1.463 (3)	C16—C17	1.396 (4)
C1—C2	1.400 (3)	C16—H16A	0.9300
C1—C6	1.406 (3)	C17—C18	1.388 (4)
C2—C3	1.398 (4)	C17—H17A	0.9300
C2—H2A	0.9300	C18—H18A	0.9300
C3—C4	1.392 (4)	C19—C20	1.502 (3)
C3—H3A	0.9300	C20—C25	1.388 (3)
C4—C5	1.385 (4)	C20—C21	1.392 (3)
C4—H4A	0.9300	C21—C22	1.387 (4)
C5—C6	1.400 (4)	C21—H21A	0.9300
C5—H5A	0.9300	C22—C23	1.382 (4)
C6—H6A	0.9300	C22—H22A	0.9300
C7—C12	1.396 (4)	C23—C24	1.380 (4)
C7—C8	1.397 (4)	C24—C25	1.378 (3)
C8—C9	1.390 (4)	C24—H24A	0.9300
C8—H8A	0.9300
C7—Sn1—C1	115.46 (9)	C9—C10—H10A	120.3
C7—Sn1—C13	124.90 (9)	C10—C11—C12	120.9 (3)
C1—Sn1—C13	119.61 (9)	C10—C11—H11A	119.6
C7—Sn1—O2^i	89.85 (9)	C12—C11—H11A	119.6
C1—Sn1—O2^i	95.25 (8)	C11—C12—C7	120.1 (3)
C13—Sn1—O2^i	87.22 (8)	C11—C12—H12A	119.9
C7—Sn1—O1	87.89 (9)	C7—C12—H12A	119.9
C1—Sn1—O1	93.78 (8)	C18—C13—C14	118.0 (2)
C13—Sn1—O1	86.75 (8)	C18—C13—Sn1	120.80 (18)
O2^i—Sn1—O1	170.79 (7)	C14—C13—Sn1	121.12 (18)
C19—O1—Sn1	142.06 (16)	C15—C14—C13	120.6 (3)
C19—O2—Sn1^ii	141.46 (17)	C15—C14—H14A	119.7
O4—N1—O3	125.3 (2)	C13—C14—H14A	119.7
O4—N1—C25	117.7 (2)	C16—C15—C14	120.8 (3)
O3—N1—C25	117.0 (2)	C16—C15—H15A	119.6
O6—N2—O5	124.1 (3)	C14—C15—H15A	119.6
O6—N2—C23	118.6 (2)	C15—C16—C17	119.1 (3)
O5—N2—C23	117.3 (3)	C15—C16—H16A	120.4
C2—C1—C6	118.8 (2)	C17—C16—H16A	120.4
C2—C1—Sn1	122.94 (18)	C18—C17—C16	120.4 (3)
C6—C1—Sn1	118.29 (17)	C18—C17—H17A	119.8
C3—C2—C1	120.3 (2)	C16—C17—H17A	119.8
C3—C2—H2A	119.9	C17—C18—C13	121.2 (3)
C1—C2—H2A	119.9	C17—C18—H18A	119.4
C4—C3—C2	120.5 (2)	C13—C18—H18A	119.4
C4—C3—H3A	119.8	O2—C19—O1	122.6 (2)
C2—C3—H3A	119.8	O2—C19—C20	117.9 (2)
C5—C4—C3	119.8 (2)	O1—C19—C20	119.1 (2)
C5—C4—H4A	120.1	C25—C20—C21	118.2 (2)
C3—C4—H4A	120.1	C25—C20—C19	124.6 (2)
C4—C5—C6	120.2 (2)	C21—C20—C19	117.2 (2)
C4—C5—H5A	119.9	C22—C21—C20	120.8 (2)
C6—C5—H5A	119.9	C22—C21—H21A	119.6
C5—C6—C1	120.5 (2)	C20—C21—H21A	119.6
C5—C6—H6A	119.8	C23—C22—C21	118.2 (2)
C1—C6—H6A	119.8	C23—C22—H22A	120.9
C12—C7—C8	118.6 (2)	C21—C22—H22A	120.9
C12—C7—Sn1	120.95 (19)	C24—C23—C22	123.1 (2)
C8—C7—Sn1	120.4 (2)	C24—C23—N2	118.4 (2)
C9—C8—C7	120.5 (3)	C22—C23—N2	118.5 (2)
C9—C8—H8A	119.8	C25—C24—C23	116.8 (2)
C7—C8—H8A	119.8	C25—C24—H24A	121.6
C10—C9—C8	120.5 (3)	C23—C24—H24A	121.6
C10—C9—H9A	119.8	C24—C25—C20	122.9 (2)
C8—C9—H9A	119.8	C24—C25—N1	117.8 (2)
C11—C10—C9	119.4 (3)	C20—C25—N1	119.4 (2)
C11—C10—H10A	120.3
C7—Sn1—O1—C19	154.9 (3)	C1—Sn1—C13—C14	69.1 (2)
C1—Sn1—O1—C19	39.5 (3)	O2^i—Sn1—C13—C14	−25.4 (2)
C13—Sn1—O1—C19	−80.0 (3)	O1—Sn1—C13—C14	161.6 (2)
C7—Sn1—C1—C2	173.48 (19)	C18—C13—C14—C15	−1.1 (4)
C13—Sn1—C1—C2	−8.6 (2)	Sn1—C13—C14—C15	175.6 (2)
O2^i—Sn1—C1—C2	81.1 (2)	C13—C14—C15—C16	−0.1 (5)
O1—Sn1—C1—C2	−97.1 (2)	C14—C15—C16—C17	1.2 (5)
C7—Sn1—C1—C6	−6.7 (2)	C15—C16—C17—C18	−1.1 (5)
C13—Sn1—C1—C6	171.17 (17)	C16—C17—C18—C13	−0.1 (4)
O2^i—Sn1—C1—C6	−99.04 (19)	C14—C13—C18—C17	1.2 (4)
O1—Sn1—C1—C6	82.76 (19)	Sn1—C13—C18—C17	−175.5 (2)
C6—C1—C2—C3	0.7 (4)	Sn1^ii—O2—C19—O1	143.0 (2)
Sn1—C1—C2—C3	−179.48 (18)	Sn1^ii—O2—C19—C20	−43.6 (4)
C1—C2—C3—C4	−0.9 (4)	Sn1—O1—C19—O2	149.4 (2)
C2—C3—C4—C5	0.4 (4)	Sn1—O1—C19—C20	−23.9 (4)
C3—C4—C5—C6	0.4 (4)	O2—C19—C20—C25	103.4 (3)
C4—C5—C6—C1	−0.6 (4)	O1—C19—C20—C25	−83.0 (3)
C2—C1—C6—C5	0.0 (4)	O2—C19—C20—C21	−76.7 (3)
Sn1—C1—C6—C5	−179.79 (19)	O1—C19—C20—C21	96.9 (3)
C1—Sn1—C7—C12	−99.5 (2)	C25—C20—C21—C22	−0.5 (4)
C13—Sn1—C7—C12	82.8 (2)	C19—C20—C21—C22	179.6 (2)
O2^i—Sn1—C7—C12	−3.7 (2)	C20—C21—C22—C23	−0.7 (4)
O1—Sn1—C7—C12	167.3 (2)	C21—C22—C23—C24	1.5 (4)
C1—Sn1—C7—C8	77.5 (2)	C21—C22—C23—N2	−178.6 (2)
C13—Sn1—C7—C8	−100.2 (2)	O6—N2—C23—C24	−17.0 (4)
O2^i—Sn1—C7—C8	173.3 (2)	O5—N2—C23—C24	163.3 (3)
O1—Sn1—C7—C8	−15.7 (2)	O6—N2—C23—C22	163.1 (3)
C12—C7—C8—C9	−0.8 (4)	O5—N2—C23—C22	−16.7 (4)
Sn1—C7—C8—C9	−177.8 (2)	C22—C23—C24—C25	−1.0 (4)
C7—C8—C9—C10	0.4 (4)	N2—C23—C24—C25	179.1 (2)
C8—C9—C10—C11	0.0 (5)	C23—C24—C25—C20	−0.3 (4)
C9—C10—C11—C12	−0.1 (5)	C23—C24—C25—N1	179.5 (2)
C10—C11—C12—C7	−0.3 (4)	C21—C20—C25—C24	1.0 (4)
C8—C7—C12—C11	0.7 (4)	C19—C20—C25—C24	−179.1 (2)
Sn1—C7—C12—C11	177.7 (2)	C21—C20—C25—N1	−178.8 (2)
C7—Sn1—C13—C18	63.3 (2)	C19—C20—C25—N1	1.1 (3)
C1—Sn1—C13—C18	−114.3 (2)	O4—N1—C25—C24	−12.5 (3)
O2^i—Sn1—C13—C18	151.2 (2)	O3—N1—C25—C24	165.9 (2)
O1—Sn1—C13—C18	−21.8 (2)	O4—N1—C25—C20	167.4 (2)
C7—Sn1—C13—C14	−113.3 (2)	O3—N1—C25—C20	−14.2 (3)

Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1	0.93	2.37	2.977 (3)	123
C18—H18A···O1	0.93	2.39	2.984 (3)	121
C12—H12A···O2^i	0.93	2.40	3.026 (3)	124
C14—H14A···O2^i	0.93	2.52	3.028 (3)	115
C17—H17A···O6^iii	0.93	2.47	3.331 (4)	153
C21—H21A···O5^iv	0.93	2.40	3.279 (3)	158

Symmetry codes: (i) x+1, y, z; (iii) x, y+1, z; (iv) −x+1, y+1/2, −z+1/2.