(2-Hydr­oxy-3,5-dinitro­benzoato)tris­(2-methyl-2-phenyl­prop­yl)tin(IV)

Tian, L.-J.; Yu, H.-X.; Sun, Y.-X.; Zhang, B.

doi:10.1107/S1600536805028904

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(2-Hydroxy-3,5-dinitrobenzoato)tris(2-methyl-2-phenylpropyl)tin(IV)

L.-J. Tian, H.-X. Yu, Y.-X. Sun and B. Zhang

The Sn atom of the title compound, [Sn(C₁₀H₁₃)₃(C₇H₃N₂O₇)], is four-coordinate and possesses a distorted tetrahedral geometry. There is an intramolecular O—H

O hydrogen bond between the carboxyl and the phenolic hydroxy groups.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805028904/bh6026sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028904/bh6026Isup2.hkl Contains datablock I

CCDC reference: 287445

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.007 Å
Disorder in main residue
R factor = 0.051
wR factor = 0.110
Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT411_ALERT_2_B Short Inter H...H Contact  H16A   ..  H16A    ..       2.08 Ang.

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.26 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.54 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.79 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C9
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
PLAT301_ALERT_3_C Main Residue  Disorder .........................       2.00 Perc.
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C12    -C17           1.37 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  10 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
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Recently, we have reported several structures of tris(2-methyl-2-phenylpropyl)tin carboxylates, such as tris(2-methyl-2-phenylpropyl)tin pyridine-3-carboxylate (Tian, Sun, Yang & Yang, 2005), 3,5-dinitrobenzoate (Tian, Yu, Sun, & Zhang, 2005) and bis[tris(2-methyl-2-phenylpropyl)tin(IV)] phthalate (Tian, Sun, Yang & Ng, 2005), which all present a distorted tetrahedral geometry. In the title compound, (I), tetrahedral coordination is also observed (Fig. 1).

The Sn1···O2 separation of 3.118 (3) Å indicates a weak interaction between these atoms, which distorts the tetrahedral geometry. Bond dimensions around the Sn atom (Table 1) are similar to those found in the carboxylate structures mentioned above. An intramolecular O—H···O hydrogen bond is observed between the carboxyl and the phenolic hydroxy groups (Fig. 1 and Table 2). The OH group is disordered over two ortho positions, and both O atoms of the carboxylate functionality may serve as acceptor for the intramolecular hydrogen bonding, giving hydrogen bonds of very similar strengths. An unbalanced statistical distribution, 0.836 (7)/0.164 (7), clearly reflects the fact that atom O2 is a better acceptor than O1.

Experimental top

Bis[tris(2-methyl-2-phenylpropyl)tin] oxide (1.05 g, 1 mmol) and 2-hydroxy-3,5-dinitrobenzoic acid (0.46 g, 2 mmol) in toluene (50 ml) were refluxed for 5 h with azeotropic removal of water via a Dean–Stark trap. The resulting clear solution was evaporated under reduced pressure. The white solid obtained, (I), was purified by recrystallization from ethanol and crystals were obtained from a chloroform–hexane (1:1 v/v) solution by slow evaporation at 298 K (yield 73%, m.p. 382–383 K). Analysis found: C 59.76, H 5.59, N 3.65%; calculated for C₃₇H₄₂N₂O₇Sn: C 59.61, H 5.68, N 3.76%. IR (KBr disc): ν_as(CO₂) 1651, ν_s(CO₂) 1340, ν_as(NO₂) 1536, ν_s(NO₂) 1398 cm⁻¹; ¹H NMR (400 MHz, CDCl₃, TMS as reference): δ 9.31 (2H, s, nitrobenzene H), 7.28–7.05 (15H, m, 3× C₆H₅), 5.17 (1H, s, OH), 1.30 (6H, s, 3 × CH₂Sn), 1.24 (18H, s, 6 × CH₃); ¹¹⁹Sn NMR (111.9 MHz, CDCl₃, Me₄Sn as reference): δ 112.3.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Bruker, 2002).

Figures top

Fig. 1. The structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. The disordered hydroxy group (O7a/O7b) is represented with different bond styles. Except for the OH groups, H atoms have been omitted. Hydrogen bonds are shown as dashed lines.

(2-Hydroxy-3,5-dinitrobenzoato)tris(2-methyl-2-phenylpropyl)tin(IV) top

Crystal data top

[Sn(C₁₀H₁₃)₃(C₇H₃N₂O₇)]	F(000) = 1536
M_r = 745.42	D_x = 1.382 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 382–383 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.0060 (8) Å	Cell parameters from 7082 reflections
b = 22.6236 (18) Å	θ = 2.3–25.6°
c = 15.8991 (13) Å	µ = 0.76 mm⁻¹
β = 95.512 (1)°	T = 295 K
V = 3582.5 (5) Å³	Needle, pale yellow
Z = 4	0.25 × 0.10 × 0.08 mm

Data collection top

Bruker APEX area-detector diffractometer	6649 independent reflections
Radiation source: fine-focus sealed tube	5673 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 25.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −12→12
T_min = 0.832, T_max = 0.942	k = −27→26
26672 measured reflections	l = −19→19

Refinement top

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 1.18	w = 1/[σ²(F_o²) + (0.0384P)² + 1.8962P] where P = (F_o² + 2F_c²)/3
6649 reflections	(Δ/σ)_max = 0.001
434 parameters	Δρ_max = 0.91 e Å⁻³
0 restraints	Δρ_min = −0.79 e Å⁻³

Crystal data top

[Sn(C₁₀H₁₃)₃(C₇H₃N₂O₇)]	V = 3582.5 (5) Å³
M_r = 745.42	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.0060 (8) Å	µ = 0.76 mm⁻¹
b = 22.6236 (18) Å	T = 295 K
c = 15.8991 (13) Å	0.25 × 0.10 × 0.08 mm
β = 95.512 (1)°

Data collection top

Bruker APEX area-detector diffractometer	6649 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	5673 reflections with I > 2σ(I)
T_min = 0.832, T_max = 0.942	R_int = 0.040
26672 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.18	Δρ_max = 0.91 e Å⁻³
6649 reflections	Δρ_min = −0.79 e Å⁻³
434 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sn1	0.75430 (3)	0.136619 (12)	0.200914 (17)	0.04532 (11)
N1	0.4673 (4)	0.05564 (18)	0.6336 (3)	0.0657 (10)
N2	0.9175 (4)	0.13747 (18)	0.6439 (3)	0.0696 (11)
O1	0.7476 (3)	0.13951 (13)	0.33301 (18)	0.0572 (8)
O2	0.5475 (3)	0.09727 (15)	0.32461 (17)	0.0647 (8)
O3	0.3636 (4)	0.04078 (18)	0.5962 (2)	0.0875 (11)
O4	0.4885 (5)	0.0515 (3)	0.7080 (2)	0.145 (2)
O5	0.9129 (4)	0.1439 (2)	0.7188 (3)	0.1047 (14)
O6	1.0166 (4)	0.1445 (2)	0.6084 (3)	0.1080 (15)
O7A	0.4527 (3)	0.06278 (15)	0.4543 (2)	0.0572 (12)	0.836 (7)
H7AA	0.4590	0.0694	0.4041	0.086*	0.836 (7)
O7B	0.8906 (18)	0.1494 (8)	0.4674 (11)	0.062 (6)	0.164 (7)
H7BA	0.8696	0.1518	0.4164	0.093*	0.164 (7)
C1	0.6512 (4)	0.11486 (18)	0.3663 (3)	0.0484 (10)
C2	0.6668 (4)	0.10744 (16)	0.4591 (2)	0.0402 (8)
C3	0.5617 (4)	0.08252 (17)	0.4998 (2)	0.0432 (9)
H3A	0.4844	0.0689	0.4686	0.052*	0.164 (7)
C4	0.5753 (4)	0.07866 (17)	0.5875 (2)	0.0475 (10)
C5	0.6915 (4)	0.09691 (17)	0.6341 (2)	0.0510 (10)
H5A	0.6996	0.0942	0.6928	0.061*
C6	0.7942 (4)	0.11892 (17)	0.5930 (3)	0.0477 (10)
C7	0.7846 (4)	0.12503 (16)	0.5065 (2)	0.0436 (9)
H7A	0.8557	0.1407	0.4800	0.052*	0.836 (7)
C8	0.7357 (4)	0.04361 (19)	0.1758 (3)	0.0604 (12)
H8A	0.6879	0.0262	0.2200	0.072*
H8B	0.6794	0.0388	0.1231	0.072*
C9	0.8638 (5)	0.0077 (2)	0.1696 (3)	0.0694 (14)
C10	0.8289 (7)	−0.0589 (3)	0.1712 (5)	0.126 (3)
H10A	0.7938	−0.0684	0.2237	0.190*
H10B	0.9084	−0.0818	0.1658	0.190*
H10C	0.7629	−0.0679	0.1251	0.190*
C11	0.9170 (6)	0.0221 (4)	0.0861 (3)	0.131 (3)
H11A	0.9977	0.0000	0.0810	0.197*
H11B	0.9360	0.0636	0.0837	0.197*
H11C	0.8509	0.0117	0.0407	0.197*
C12	0.9672 (4)	0.02012 (18)	0.2441 (3)	0.0508 (10)
C13	1.0995 (5)	0.0349 (2)	0.2367 (3)	0.0731 (14)
H13A	1.1296	0.0369	0.1833	0.088*
C14	1.1869 (6)	0.0465 (2)	0.3056 (5)	0.0900 (18)
H14A	1.2756	0.0561	0.2985	0.108*
C15	1.1462 (7)	0.0443 (3)	0.3840 (4)	0.0918 (19)
H15A	1.2060	0.0529	0.4309	0.110*
C16	1.0183 (7)	0.0297 (3)	0.3939 (3)	0.0936 (19)
H16A	0.9897	0.0280	0.4478	0.112*
C17	0.9288 (5)	0.0170 (2)	0.3239 (3)	0.0693 (13)
H17A	0.8412	0.0062	0.3317	0.083*
C18	0.5884 (4)	0.19067 (18)	0.1524 (3)	0.0518 (10)
H18A	0.5381	0.2016	0.1992	0.062*
H18B	0.6241	0.2268	0.1304	0.062*
C19	0.4901 (4)	0.16341 (19)	0.0829 (3)	0.0535 (10)
C20	0.3972 (5)	0.1205 (2)	0.1240 (3)	0.0756 (14)
H20A	0.4493	0.0888	0.1504	0.113*
H20B	0.3321	0.1048	0.0816	0.113*
H20C	0.3519	0.1411	0.1658	0.113*
C21	0.4035 (5)	0.2138 (2)	0.0402 (3)	0.0785 (15)
H21A	0.3413	0.1977	−0.0035	0.118*
H21B	0.4608	0.2420	0.0161	0.118*
H21C	0.3549	0.2331	0.0816	0.118*
C22	0.5646 (4)	0.13433 (18)	0.0146 (3)	0.0523 (10)
C23	0.6813 (5)	0.1590 (2)	−0.0108 (3)	0.0624 (12)
H23A	0.7150	0.1933	0.0157	0.075*
C24	0.7488 (6)	0.1347 (2)	−0.0733 (3)	0.0741 (14)
H24A	0.8266	0.1525	−0.0886	0.089*
C25	0.7019 (6)	0.0840 (3)	−0.1136 (3)	0.0813 (16)
H25A	0.7475	0.0671	−0.1558	0.098*
C26	0.5874 (7)	0.0592 (3)	−0.0905 (3)	0.0925 (19)
H26A	0.5540	0.0252	−0.1180	0.111*
C27	0.5201 (5)	0.0830 (2)	−0.0275 (3)	0.0746 (15)
H27A	0.4429	0.0644	−0.0125	0.090*
C28	0.9518 (4)	0.1746 (2)	0.2141 (3)	0.0615 (12)
H28A	0.9957	0.1616	0.2680	0.074*
H28B	1.0013	0.1575	0.1705	0.074*
C29	0.9684 (4)	0.2424 (2)	0.2097 (3)	0.0642 (12)
C30	0.8824 (6)	0.2718 (2)	0.2720 (3)	0.0921 (18)
H30A	0.7894	0.2635	0.2558	0.138*
H30B	0.8968	0.3137	0.2716	0.138*
H30C	0.9070	0.2566	0.3278	0.138*
C31	1.1175 (5)	0.2568 (3)	0.2372 (4)	0.099 (2)
H31A	1.1310	0.2988	0.2350	0.149*
H31B	1.1735	0.2375	0.1998	0.149*
H31C	1.1404	0.2431	0.2939	0.149*
C32	0.9338 (4)	0.2627 (2)	0.1189 (3)	0.0607 (12)
C33	1.0066 (5)	0.2416 (2)	0.0565 (3)	0.0789 (16)
H33A	1.0771	0.2156	0.0708	0.095*
C34	0.9775 (7)	0.2580 (3)	−0.0276 (4)	0.107 (2)
H34A	1.0282	0.2435	−0.0690	0.129*
C35	0.8718 (8)	0.2965 (4)	−0.0487 (5)	0.112 (3)
H35A	0.8500	0.3076	−0.1046	0.134*
C36	0.8013 (7)	0.3175 (3)	0.0123 (5)	0.106 (2)
H36A	0.7306	0.3434	−0.0021	0.127*
C37	0.8305 (5)	0.3021 (2)	0.0951 (4)	0.0772 (15)
H37A	0.7806	0.3181	0.1360	0.093*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.04331 (17)	0.05069 (18)	0.04213 (17)	−0.00028 (13)	0.00501 (12)	0.00590 (13)
N1	0.076 (3)	0.072 (3)	0.052 (2)	−0.019 (2)	0.019 (2)	0.001 (2)
N2	0.062 (3)	0.072 (3)	0.070 (3)	−0.007 (2)	−0.017 (2)	0.010 (2)
O1	0.0608 (18)	0.066 (2)	0.0451 (16)	−0.0123 (15)	0.0079 (14)	0.0068 (14)
O2	0.0565 (18)	0.092 (2)	0.0439 (17)	−0.0157 (17)	−0.0036 (14)	0.0021 (16)
O3	0.066 (2)	0.113 (3)	0.086 (3)	−0.022 (2)	0.020 (2)	0.013 (2)
O4	0.146 (4)	0.240 (6)	0.051 (2)	−0.098 (4)	0.020 (3)	0.010 (3)
O5	0.096 (3)	0.149 (4)	0.062 (3)	−0.008 (3)	−0.030 (2)	−0.012 (2)
O6	0.063 (2)	0.158 (4)	0.099 (3)	−0.032 (3)	−0.016 (2)	0.000 (3)
O7A	0.045 (2)	0.067 (2)	0.058 (2)	−0.0136 (17)	−0.0016 (16)	0.0018 (18)
O7B	0.063 (12)	0.071 (13)	0.052 (11)	−0.027 (10)	0.001 (9)	−0.006 (9)
C1	0.052 (3)	0.049 (2)	0.044 (2)	0.003 (2)	0.006 (2)	0.0005 (19)
C2	0.039 (2)	0.039 (2)	0.042 (2)	0.0008 (16)	0.0005 (16)	−0.0015 (16)
C3	0.041 (2)	0.043 (2)	0.046 (2)	0.0018 (17)	0.0038 (17)	−0.0008 (17)
C4	0.056 (2)	0.039 (2)	0.049 (2)	−0.0021 (18)	0.0113 (19)	−0.0004 (18)
C5	0.069 (3)	0.044 (2)	0.038 (2)	0.000 (2)	−0.002 (2)	0.0044 (18)
C6	0.048 (2)	0.042 (2)	0.051 (2)	0.0009 (18)	−0.0078 (19)	−0.0010 (18)
C7	0.045 (2)	0.038 (2)	0.048 (2)	−0.0019 (17)	0.0038 (18)	0.0055 (17)
C8	0.060 (3)	0.057 (3)	0.061 (3)	0.005 (2)	−0.008 (2)	−0.005 (2)
C9	0.071 (3)	0.078 (3)	0.056 (3)	0.025 (3)	−0.010 (2)	−0.013 (2)
C10	0.124 (5)	0.072 (4)	0.167 (7)	0.037 (4)	−0.068 (5)	−0.049 (4)
C11	0.121 (5)	0.215 (8)	0.056 (4)	0.087 (6)	0.007 (3)	−0.024 (4)
C12	0.052 (3)	0.048 (2)	0.052 (3)	0.0129 (19)	0.004 (2)	0.0041 (19)
C13	0.061 (3)	0.082 (4)	0.079 (4)	0.016 (3)	0.018 (3)	0.021 (3)
C14	0.057 (3)	0.078 (4)	0.130 (6)	−0.001 (3)	−0.020 (4)	0.015 (4)
C15	0.093 (5)	0.087 (4)	0.087 (4)	0.020 (4)	−0.036 (4)	−0.013 (3)
C16	0.106 (5)	0.119 (5)	0.054 (3)	0.034 (4)	0.001 (3)	0.010 (3)
C17	0.061 (3)	0.085 (4)	0.063 (3)	0.007 (3)	0.005 (2)	0.023 (3)
C18	0.051 (2)	0.050 (2)	0.056 (3)	0.008 (2)	0.010 (2)	0.007 (2)
C19	0.043 (2)	0.057 (3)	0.058 (3)	−0.001 (2)	−0.003 (2)	0.010 (2)
C20	0.057 (3)	0.090 (4)	0.080 (4)	−0.010 (3)	0.008 (3)	0.011 (3)
C21	0.061 (3)	0.087 (4)	0.085 (4)	0.014 (3)	−0.008 (3)	0.019 (3)
C22	0.056 (3)	0.052 (2)	0.046 (2)	−0.006 (2)	−0.0112 (19)	0.012 (2)
C23	0.072 (3)	0.062 (3)	0.054 (3)	−0.016 (2)	0.010 (2)	−0.005 (2)
C24	0.085 (4)	0.080 (4)	0.058 (3)	−0.009 (3)	0.013 (3)	−0.003 (3)
C25	0.120 (5)	0.081 (4)	0.042 (3)	0.012 (4)	0.004 (3)	−0.004 (3)
C26	0.144 (6)	0.075 (4)	0.055 (3)	−0.025 (4)	−0.010 (4)	−0.010 (3)
C27	0.085 (4)	0.077 (4)	0.058 (3)	−0.030 (3)	−0.011 (3)	0.004 (3)
C28	0.042 (2)	0.075 (3)	0.067 (3)	−0.007 (2)	0.002 (2)	0.019 (2)
C29	0.055 (3)	0.070 (3)	0.066 (3)	−0.014 (2)	−0.001 (2)	0.007 (2)
C30	0.113 (5)	0.084 (4)	0.081 (4)	−0.013 (4)	0.018 (3)	−0.016 (3)
C31	0.075 (4)	0.119 (5)	0.098 (4)	−0.040 (3)	−0.022 (3)	0.027 (4)
C32	0.047 (3)	0.060 (3)	0.075 (3)	−0.019 (2)	0.004 (2)	0.012 (2)
C33	0.066 (3)	0.090 (4)	0.081 (4)	−0.022 (3)	0.011 (3)	0.016 (3)
C34	0.105 (5)	0.131 (6)	0.087 (5)	−0.056 (5)	0.023 (4)	0.009 (4)
C35	0.116 (6)	0.122 (6)	0.089 (5)	−0.070 (5)	−0.027 (4)	0.051 (5)
C36	0.093 (5)	0.084 (5)	0.132 (6)	−0.036 (4)	−0.028 (4)	0.056 (5)
C37	0.062 (3)	0.058 (3)	0.110 (5)	−0.017 (3)	−0.002 (3)	0.019 (3)

Geometric parameters (Å, º) top

Sn1—O1	2.109 (3)	C17—H17A	0.9300
Sn1—C18	2.144 (4)	C18—C19	1.536 (6)
Sn1—C8	2.146 (4)	C18—H18A	0.9700
Sn1—C28	2.147 (4)	C18—H18B	0.9700
N1—O4	1.185 (5)	C19—C22	1.524 (6)
N1—O3	1.194 (5)	C19—C20	1.533 (6)
N1—C4	1.459 (5)	C19—C21	1.549 (6)
N2—O6	1.198 (5)	C20—H20A	0.9600
N2—O5	1.205 (5)	C20—H20B	0.9600
N2—C6	1.470 (5)	C20—H20C	0.9600
O1—C1	1.273 (5)	C21—H21A	0.9600
O2—C1	1.242 (5)	C21—H21B	0.9600
O7A—C3	1.326 (5)	C21—H21C	0.9600
O7A—H7AA	0.8200	C22—C23	1.389 (6)
O7B—C7	1.393 (17)	C22—C27	1.392 (6)
O7B—H7BA	0.8200	C23—C24	1.370 (6)
C1—C2	1.479 (5)	C23—H23A	0.9300
C2—C7	1.394 (5)	C24—C25	1.373 (7)
C2—C3	1.405 (5)	C24—H24A	0.9300
C3—C4	1.391 (5)	C25—C26	1.357 (8)
C3—H3A	0.9300	C25—H25A	0.9300
C4—C5	1.381 (5)	C26—C27	1.371 (7)
C5—C6	1.364 (6)	C26—H26A	0.9300
C5—H5A	0.9300	C27—H27A	0.9300
C6—C7	1.377 (5)	C28—C29	1.544 (6)
C7—H7A	0.9300	C28—H28A	0.9700
C8—C9	1.529 (6)	C28—H28B	0.9700
C8—H8A	0.9700	C29—C32	1.524 (6)
C8—H8B	0.9700	C29—C30	1.525 (7)
C9—C11	1.512 (7)	C29—C31	1.549 (6)
C9—C12	1.522 (6)	C30—H30A	0.9600
C9—C10	1.547 (8)	C30—H30B	0.9600
C10—H10A	0.9600	C30—H30C	0.9600
C10—H10B	0.9600	C31—H31A	0.9600
C10—H10C	0.9600	C31—H31B	0.9600
C11—H11A	0.9600	C31—H31C	0.9600
C11—H11B	0.9600	C32—C33	1.372 (7)
C11—H11C	0.9600	C32—C37	1.389 (6)
C12—C17	1.363 (6)	C33—C34	1.392 (7)
C12—C13	1.381 (6)	C33—H33A	0.9300
C13—C14	1.359 (7)	C34—C35	1.385 (9)
C13—H13A	0.9300	C34—H34A	0.9300
C14—C15	1.350 (8)	C35—C36	1.340 (10)
C14—H14A	0.9300	C35—H35A	0.9300
C15—C16	1.345 (8)	C36—C37	1.366 (8)
C15—H15A	0.9300	C36—H36A	0.9300
C16—C17	1.389 (7)	C37—H37A	0.9300
C16—H16A	0.9300

O1—Sn1—C18	104.07 (14)	C19—C18—H18A	108.1
O1—Sn1—C8	101.84 (15)	Sn1—C18—H18A	108.1
C18—Sn1—C8	116.22 (16)	C19—C18—H18B	108.1
O1—Sn1—C28	90.41 (15)	Sn1—C18—H18B	108.1
C18—Sn1—C28	118.70 (17)	H18A—C18—H18B	107.3
C8—Sn1—C28	118.25 (17)	C22—C19—C20	112.9 (4)
O4—N1—O3	122.6 (4)	C22—C19—C18	111.3 (3)
O4—N1—C4	117.3 (4)	C20—C19—C18	108.7 (4)
O3—N1—C4	120.0 (4)	C22—C19—C21	107.2 (4)
O6—N2—O5	124.2 (5)	C20—C19—C21	108.4 (4)
O6—N2—C6	117.9 (4)	C18—C19—C21	108.2 (4)
O5—N2—C6	117.9 (5)	C19—C20—H20A	109.5
C1—O1—Sn1	119.9 (3)	C19—C20—H20B	109.5
C3—O7A—H7AA	109.5	H20A—C20—H20B	109.5
C7—O7B—H7BA	109.5	C19—C20—H20C	109.5
O2—C1—O1	123.1 (4)	H20A—C20—H20C	109.5
O2—C1—C2	120.0 (4)	H20B—C20—H20C	109.5
O1—C1—C2	116.9 (4)	C19—C21—H21A	109.5
C7—C2—C3	119.9 (3)	C19—C21—H21B	109.5
C7—C2—C1	120.6 (4)	H21A—C21—H21B	109.5
C3—C2—C1	119.5 (3)	C19—C21—H21C	109.5
O7A—C3—C4	121.4 (4)	H21A—C21—H21C	109.5
O7A—C3—C2	119.8 (4)	H21B—C21—H21C	109.5
C4—C3—C2	118.7 (3)	C23—C22—C27	115.8 (5)
C4—C3—H3A	120.6	C23—C22—C19	121.1 (4)
C2—C3—H3A	120.6	C27—C22—C19	123.1 (4)
C5—C4—C3	121.1 (4)	C24—C23—C22	122.4 (4)
C5—C4—N1	117.6 (4)	C24—C23—H23A	118.8
C3—C4—N1	121.4 (4)	C22—C23—H23A	118.8
C6—C5—C4	119.1 (4)	C23—C24—C25	120.2 (5)
C6—C5—H5A	120.4	C23—C24—H24A	119.9
C4—C5—H5A	120.4	C25—C24—H24A	119.9
C5—C6—C7	122.1 (4)	C26—C25—C24	118.6 (5)
C5—C6—N2	118.2 (4)	C26—C25—H25A	120.7
C7—C6—N2	119.7 (4)	C24—C25—H25A	120.7
C6—C7—O7B	120.1 (8)	C25—C26—C27	121.5 (5)
C6—C7—C2	119.0 (4)	C25—C26—H26A	119.3
O7B—C7—C2	120.8 (8)	C27—C26—H26A	119.3
C6—C7—H7A	120.5	C26—C27—C22	121.5 (5)
C2—C7—H7A	120.5	C26—C27—H27A	119.3
C9—C8—Sn1	118.3 (3)	C22—C27—H27A	119.3
C9—C8—H8A	107.7	C29—C28—Sn1	119.7 (3)
Sn1—C8—H8A	107.7	C29—C28—H28A	107.4
C9—C8—H8B	107.7	Sn1—C28—H28A	107.4
Sn1—C8—H8B	107.7	C29—C28—H28B	107.4
H8A—C8—H8B	107.1	Sn1—C28—H28B	107.4
C11—C9—C12	111.9 (5)	H28A—C28—H28B	106.9
C11—C9—C8	108.1 (4)	C32—C29—C30	113.1 (4)
C12—C9—C8	111.3 (4)	C32—C29—C28	109.1 (4)
C11—C9—C10	108.8 (5)	C30—C29—C28	109.5 (4)
C12—C9—C10	107.7 (4)	C32—C29—C31	109.2 (4)
C8—C9—C10	108.9 (4)	C30—C29—C31	108.2 (4)
C9—C10—H10A	109.5	C28—C29—C31	107.5 (4)
C9—C10—H10B	109.5	C29—C30—H30A	109.5
H10A—C10—H10B	109.5	C29—C30—H30B	109.5
C9—C10—H10C	109.5	H30A—C30—H30B	109.5
H10A—C10—H10C	109.5	C29—C30—H30C	109.5
H10B—C10—H10C	109.5	H30A—C30—H30C	109.5
C9—C11—H11A	109.5	H30B—C30—H30C	109.5
C9—C11—H11B	109.5	C29—C31—H31A	109.5
H11A—C11—H11B	109.5	C29—C31—H31B	109.5
C9—C11—H11C	109.5	H31A—C31—H31B	109.5
H11A—C11—H11C	109.5	C29—C31—H31C	109.5
H11B—C11—H11C	109.5	H31A—C31—H31C	109.5
C17—C12—C13	116.7 (4)	H31B—C31—H31C	109.5
C17—C12—C9	118.9 (4)	C33—C32—C37	117.4 (5)
C13—C12—C9	124.3 (4)	C33—C32—C29	119.5 (5)
C14—C13—C12	121.8 (5)	C37—C32—C29	123.1 (5)
C14—C13—H13A	119.1	C32—C33—C34	121.6 (6)
C12—C13—H13A	119.1	C32—C33—H33A	119.2
C15—C14—C13	120.6 (6)	C34—C33—H33A	119.2
C15—C14—H14A	119.7	C35—C34—C33	119.0 (7)
C13—C14—H14A	119.7	C35—C34—H34A	120.5
C16—C15—C14	119.5 (6)	C33—C34—H34A	120.5
C16—C15—H15A	120.3	C36—C35—C34	119.4 (7)
C14—C15—H15A	120.3	C36—C35—H35A	120.3
C15—C16—C17	120.3 (5)	C34—C35—H35A	120.3
C15—C16—H16A	119.8	C35—C36—C37	121.9 (7)
C17—C16—H16A	119.8	C35—C36—H36A	119.1
C12—C17—C16	121.1 (5)	C37—C36—H36A	119.1
C12—C17—H17A	119.4	C36—C37—C32	120.7 (6)
C16—C17—H17A	119.4	C36—C37—H37A	119.7
C19—C18—Sn1	116.7 (3)	C32—C37—H37A	119.7

C18—Sn1—O1—C1	68.1 (3)	C17—C12—C13—C14	−0.9 (7)
C8—Sn1—O1—C1	−53.1 (3)	C9—C12—C13—C14	178.8 (5)
C28—Sn1—O1—C1	−172.1 (3)	C12—C13—C14—C15	−0.4 (9)
Sn1—O1—C1—O2	−12.5 (6)	C13—C14—C15—C16	0.9 (9)
Sn1—O1—C1—C2	167.4 (3)	C14—C15—C16—C17	−0.1 (9)
O2—C1—C2—C7	177.7 (4)	C13—C12—C17—C16	1.7 (7)
O1—C1—C2—C7	−2.2 (6)	C9—C12—C17—C16	−178.0 (5)
O2—C1—C2—C3	−2.5 (6)	C15—C16—C17—C12	−1.2 (9)
O1—C1—C2—C3	177.7 (4)	O1—Sn1—C18—C19	−128.6 (3)
C7—C2—C3—O7A	−176.2 (4)	C8—Sn1—C18—C19	−17.5 (4)
C1—C2—C3—O7A	3.9 (6)	C28—Sn1—C18—C19	133.1 (3)
C7—C2—C3—C4	3.1 (5)	Sn1—C18—C19—C22	−47.0 (4)
C1—C2—C3—C4	−176.7 (3)	Sn1—C18—C19—C20	77.9 (4)
O7A—C3—C4—C5	177.1 (4)	Sn1—C18—C19—C21	−164.6 (3)
C2—C3—C4—C5	−2.3 (6)	C20—C19—C22—C23	−159.5 (4)
O7A—C3—C4—N1	−3.3 (6)	C18—C19—C22—C23	−37.0 (5)
C2—C3—C4—N1	177.3 (4)	C21—C19—C22—C23	81.2 (5)
O4—N1—C4—C5	−3.5 (7)	C20—C19—C22—C27	22.0 (6)
O3—N1—C4—C5	178.0 (4)	C18—C19—C22—C27	144.5 (4)
O4—N1—C4—C3	177.0 (5)	C21—C19—C22—C27	−97.3 (5)
O3—N1—C4—C3	−1.6 (6)	C27—C22—C23—C24	0.2 (7)
C3—C4—C5—C6	−0.1 (6)	C19—C22—C23—C24	−178.5 (4)
N1—C4—C5—C6	−179.7 (4)	C22—C23—C24—C25	−0.1 (8)
C4—C5—C6—C7	1.7 (6)	C23—C24—C25—C26	0.5 (8)
C4—C5—C6—N2	−179.3 (4)	C24—C25—C26—C27	−1.1 (9)
O6—N2—C6—C5	164.1 (5)	C25—C26—C27—C22	1.2 (9)
O5—N2—C6—C5	−15.0 (6)	C23—C22—C27—C26	−0.7 (7)
O6—N2—C6—C7	−17.0 (6)	C19—C22—C27—C26	177.9 (5)
O5—N2—C6—C7	163.9 (4)	O1—Sn1—C28—C29	−91.6 (4)
C5—C6—C7—O7B	178.0 (10)	C18—Sn1—C28—C29	14.7 (4)
N2—C6—C7—O7B	−0.9 (11)	C8—Sn1—C28—C29	164.7 (3)
C5—C6—C7—C2	−0.9 (6)	Sn1—C28—C29—C32	−71.8 (5)
N2—C6—C7—C2	−179.8 (4)	Sn1—C28—C29—C30	52.5 (5)
C3—C2—C7—C6	−1.6 (6)	Sn1—C28—C29—C31	169.9 (3)
C1—C2—C7—C6	178.2 (4)	C30—C29—C32—C33	177.6 (4)
C3—C2—C7—O7B	179.5 (10)	C28—C29—C32—C33	−60.3 (5)
C1—C2—C7—O7B	−0.6 (11)	C31—C29—C32—C33	57.0 (6)
O1—Sn1—C8—C9	−96.0 (3)	C30—C29—C32—C37	−2.7 (6)
C18—Sn1—C8—C9	151.7 (3)	C28—C29—C32—C37	119.5 (5)
C28—Sn1—C8—C9	0.9 (4)	C31—C29—C32—C37	−123.3 (5)
Sn1—C8—C9—C11	−74.3 (5)	C37—C32—C33—C34	−0.9 (7)
Sn1—C8—C9—C12	49.0 (5)	C29—C32—C33—C34	178.9 (4)
Sn1—C8—C9—C10	167.6 (4)	C32—C33—C34—C35	−0.4 (8)
C11—C9—C12—C17	171.3 (5)	C33—C34—C35—C36	0.9 (9)
C8—C9—C12—C17	50.3 (6)	C34—C35—C36—C37	−0.1 (10)
C10—C9—C12—C17	−69.1 (6)	C35—C36—C37—C32	−1.2 (8)
C11—C9—C12—C13	−8.4 (7)	C33—C32—C37—C36	1.7 (7)
C8—C9—C12—C13	−129.4 (5)	C29—C32—C37—C36	−178.1 (4)
C10—C9—C12—C13	111.2 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7B—H7BA···O1	0.82	1.74	2.465 (18)	147
O7A—H7AA···O2	0.82	1.73	2.477 (4)	150

Experimental details

Crystal data
Chemical formula	[Sn(C₁₀H₁₃)₃(C₇H₃N₂O₇)]
M_r	745.42
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	10.0060 (8), 22.6236 (18), 15.8991 (13)
β (°)	95.512 (1)
V (Å³)	3582.5 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.76
Crystal size (mm)	0.25 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.832, 0.942
No. of measured, independent and observed [I > 2σ(I)] reflections	26672, 6649, 5673
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.110, 1.18
No. of reflections	6649
No. of parameters	434
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.91, −0.79

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97 (Bruker, 2002).

Selected geometric parameters (Å, º) top

Sn1—O1	2.109 (3)	O2—C1	1.242 (5)
Sn1—C18	2.144 (4)	O7A—C3	1.326 (5)
Sn1—C8	2.146 (4)	O7B—C7	1.393 (17)
Sn1—C28	2.147 (4)	C1—C2	1.479 (5)
O1—C1	1.273 (5)

O1—Sn1—C18	104.07 (14)	O1—Sn1—C28	90.41 (15)
O1—Sn1—C8	101.84 (15)	C18—Sn1—C28	118.70 (17)
C18—Sn1—C8	116.22 (16)	C8—Sn1—C28	118.25 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7B—H7BA···O1	0.82	1.74	2.465 (18)	147
O7A—H7AA···O2	0.82	1.73	2.477 (4)	150

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