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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805028904/bh6026sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028904/bh6026Isup2.hkl
Contains datablock I

CCDC reference: 287445

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](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): νas(CO2) 1651, νs(CO2) 1340, νas(NO2) 1536, νs(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.

Refinement top

The hydroxyl group of the hydroxydinitrobenzoate ligand is disordered over two sites. Site-occupation factors were refined with a sum constrained to 1, converging to 0.836 (7) for atom O7a and 0.164 (7) for O7b. H atoms were placed at calculated positions and were included in the refinement in the riding-model approximation [C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic H atoms; C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl H atoms; C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for methylene H atoms; O—H = 0.82 Å and Uiso(H) = 1.5Ueq(O) for hydroxy H atoms].

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
[Figure 1] 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
Mr = 745.42Dx = 1.382 Mg m3
Monoclinic, P21/nMelting point = 382–383 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 10.0060 (8) ÅCell parameters from 7082 reflections
b = 22.6236 (18) Åθ = 2.3–25.6°
c = 15.8991 (13) ŵ = 0.76 mm1
β = 95.512 (1)°T = 295 K
V = 3582.5 (5) Å3Needle, pale yellow
Z = 40.25 × 0.10 × 0.08 mm
Data collection top
Bruker APEX area-detector
diffractometer
6649 independent reflections
Radiation source: fine-focus sealed tube5673 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
ϕ and ω scansθmax = 25.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1212
Tmin = 0.832, Tmax = 0.942k = 2726
26672 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 1.18 w = 1/[σ2(Fo2) + (0.0384P)2 + 1.8962P]
where P = (Fo2 + 2Fc2)/3
6649 reflections(Δ/σ)max = 0.001
434 parametersΔρmax = 0.91 e Å3
0 restraintsΔρmin = 0.79 e Å3
Crystal data top
[Sn(C10H13)3(C7H3N2O7)]V = 3582.5 (5) Å3
Mr = 745.42Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.0060 (8) ŵ = 0.76 mm1
b = 22.6236 (18) ÅT = 295 K
c = 15.8991 (13) Å0.25 × 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)
Tmin = 0.832, Tmax = 0.942Rint = 0.040
26672 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.110H-atom parameters constrained
S = 1.18Δρmax = 0.91 e Å3
6649 reflectionsΔρmin = 0.79 e Å3
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
xyzUiso*/UeqOcc. (<1)
Sn10.75430 (3)0.136619 (12)0.200914 (17)0.04532 (11)
N10.4673 (4)0.05564 (18)0.6336 (3)0.0657 (10)
N20.9175 (4)0.13747 (18)0.6439 (3)0.0696 (11)
O10.7476 (3)0.13951 (13)0.33301 (18)0.0572 (8)
O20.5475 (3)0.09727 (15)0.32461 (17)0.0647 (8)
O30.3636 (4)0.04078 (18)0.5962 (2)0.0875 (11)
O40.4885 (5)0.0515 (3)0.7080 (2)0.145 (2)
O50.9129 (4)0.1439 (2)0.7188 (3)0.1047 (14)
O61.0166 (4)0.1445 (2)0.6084 (3)0.1080 (15)
O7A0.4527 (3)0.06278 (15)0.4543 (2)0.0572 (12)0.836 (7)
H7AA0.45900.06940.40410.086*0.836 (7)
O7B0.8906 (18)0.1494 (8)0.4674 (11)0.062 (6)0.164 (7)
H7BA0.86960.15180.41640.093*0.164 (7)
C10.6512 (4)0.11486 (18)0.3663 (3)0.0484 (10)
C20.6668 (4)0.10744 (16)0.4591 (2)0.0402 (8)
C30.5617 (4)0.08252 (17)0.4998 (2)0.0432 (9)
H3A0.48440.06890.46860.052*0.164 (7)
C40.5753 (4)0.07866 (17)0.5875 (2)0.0475 (10)
C50.6915 (4)0.09691 (17)0.6341 (2)0.0510 (10)
H5A0.69960.09420.69280.061*
C60.7942 (4)0.11892 (17)0.5930 (3)0.0477 (10)
C70.7846 (4)0.12503 (16)0.5065 (2)0.0436 (9)
H7A0.85570.14070.48000.052*0.836 (7)
C80.7357 (4)0.04361 (19)0.1758 (3)0.0604 (12)
H8A0.68790.02620.22000.072*
H8B0.67940.03880.12310.072*
C90.8638 (5)0.0077 (2)0.1696 (3)0.0694 (14)
C100.8289 (7)0.0589 (3)0.1712 (5)0.126 (3)
H10A0.79380.06840.22370.190*
H10B0.90840.08180.16580.190*
H10C0.76290.06790.12510.190*
C110.9170 (6)0.0221 (4)0.0861 (3)0.131 (3)
H11A0.99770.00000.08100.197*
H11B0.93600.06360.08370.197*
H11C0.85090.01170.04070.197*
C120.9672 (4)0.02012 (18)0.2441 (3)0.0508 (10)
C131.0995 (5)0.0349 (2)0.2367 (3)0.0731 (14)
H13A1.12960.03690.18330.088*
C141.1869 (6)0.0465 (2)0.3056 (5)0.0900 (18)
H14A1.27560.05610.29850.108*
C151.1462 (7)0.0443 (3)0.3840 (4)0.0918 (19)
H15A1.20600.05290.43090.110*
C161.0183 (7)0.0297 (3)0.3939 (3)0.0936 (19)
H16A0.98970.02800.44780.112*
C170.9288 (5)0.0170 (2)0.3239 (3)0.0693 (13)
H17A0.84120.00620.33170.083*
C180.5884 (4)0.19067 (18)0.1524 (3)0.0518 (10)
H18A0.53810.20160.19920.062*
H18B0.62410.22680.13040.062*
C190.4901 (4)0.16341 (19)0.0829 (3)0.0535 (10)
C200.3972 (5)0.1205 (2)0.1240 (3)0.0756 (14)
H20A0.44930.08880.15040.113*
H20B0.33210.10480.08160.113*
H20C0.35190.14110.16580.113*
C210.4035 (5)0.2138 (2)0.0402 (3)0.0785 (15)
H21A0.34130.19770.00350.118*
H21B0.46080.24200.01610.118*
H21C0.35490.23310.08160.118*
C220.5646 (4)0.13433 (18)0.0146 (3)0.0523 (10)
C230.6813 (5)0.1590 (2)0.0108 (3)0.0624 (12)
H23A0.71500.19330.01570.075*
C240.7488 (6)0.1347 (2)0.0733 (3)0.0741 (14)
H24A0.82660.15250.08860.089*
C250.7019 (6)0.0840 (3)0.1136 (3)0.0813 (16)
H25A0.74750.06710.15580.098*
C260.5874 (7)0.0592 (3)0.0905 (3)0.0925 (19)
H26A0.55400.02520.11800.111*
C270.5201 (5)0.0830 (2)0.0275 (3)0.0746 (15)
H27A0.44290.06440.01250.090*
C280.9518 (4)0.1746 (2)0.2141 (3)0.0615 (12)
H28A0.99570.16160.26800.074*
H28B1.00130.15750.17050.074*
C290.9684 (4)0.2424 (2)0.2097 (3)0.0642 (12)
C300.8824 (6)0.2718 (2)0.2720 (3)0.0921 (18)
H30A0.78940.26350.25580.138*
H30B0.89680.31370.27160.138*
H30C0.90700.25660.32780.138*
C311.1175 (5)0.2568 (3)0.2372 (4)0.099 (2)
H31A1.13100.29880.23500.149*
H31B1.17350.23750.19980.149*
H31C1.14040.24310.29390.149*
C320.9338 (4)0.2627 (2)0.1189 (3)0.0607 (12)
C331.0066 (5)0.2416 (2)0.0565 (3)0.0789 (16)
H33A1.07710.21560.07080.095*
C340.9775 (7)0.2580 (3)0.0276 (4)0.107 (2)
H34A1.02820.24350.06900.129*
C350.8718 (8)0.2965 (4)0.0487 (5)0.112 (3)
H35A0.85000.30760.10460.134*
C360.8013 (7)0.3175 (3)0.0123 (5)0.106 (2)
H36A0.73060.34340.00210.127*
C370.8305 (5)0.3021 (2)0.0951 (4)0.0772 (15)
H37A0.78060.31810.13600.093*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.04331 (17)0.05069 (18)0.04213 (17)0.00028 (13)0.00501 (12)0.00590 (13)
N10.076 (3)0.072 (3)0.052 (2)0.019 (2)0.019 (2)0.001 (2)
N20.062 (3)0.072 (3)0.070 (3)0.007 (2)0.017 (2)0.010 (2)
O10.0608 (18)0.066 (2)0.0451 (16)0.0123 (15)0.0079 (14)0.0068 (14)
O20.0565 (18)0.092 (2)0.0439 (17)0.0157 (17)0.0036 (14)0.0021 (16)
O30.066 (2)0.113 (3)0.086 (3)0.022 (2)0.020 (2)0.013 (2)
O40.146 (4)0.240 (6)0.051 (2)0.098 (4)0.020 (3)0.010 (3)
O50.096 (3)0.149 (4)0.062 (3)0.008 (3)0.030 (2)0.012 (2)
O60.063 (2)0.158 (4)0.099 (3)0.032 (3)0.016 (2)0.000 (3)
O7A0.045 (2)0.067 (2)0.058 (2)0.0136 (17)0.0016 (16)0.0018 (18)
O7B0.063 (12)0.071 (13)0.052 (11)0.027 (10)0.001 (9)0.006 (9)
C10.052 (3)0.049 (2)0.044 (2)0.003 (2)0.006 (2)0.0005 (19)
C20.039 (2)0.039 (2)0.042 (2)0.0008 (16)0.0005 (16)0.0015 (16)
C30.041 (2)0.043 (2)0.046 (2)0.0018 (17)0.0038 (17)0.0008 (17)
C40.056 (2)0.039 (2)0.049 (2)0.0021 (18)0.0113 (19)0.0004 (18)
C50.069 (3)0.044 (2)0.038 (2)0.000 (2)0.002 (2)0.0044 (18)
C60.048 (2)0.042 (2)0.051 (2)0.0009 (18)0.0078 (19)0.0010 (18)
C70.045 (2)0.038 (2)0.048 (2)0.0019 (17)0.0038 (18)0.0055 (17)
C80.060 (3)0.057 (3)0.061 (3)0.005 (2)0.008 (2)0.005 (2)
C90.071 (3)0.078 (3)0.056 (3)0.025 (3)0.010 (2)0.013 (2)
C100.124 (5)0.072 (4)0.167 (7)0.037 (4)0.068 (5)0.049 (4)
C110.121 (5)0.215 (8)0.056 (4)0.087 (6)0.007 (3)0.024 (4)
C120.052 (3)0.048 (2)0.052 (3)0.0129 (19)0.004 (2)0.0041 (19)
C130.061 (3)0.082 (4)0.079 (4)0.016 (3)0.018 (3)0.021 (3)
C140.057 (3)0.078 (4)0.130 (6)0.001 (3)0.020 (4)0.015 (4)
C150.093 (5)0.087 (4)0.087 (4)0.020 (4)0.036 (4)0.013 (3)
C160.106 (5)0.119 (5)0.054 (3)0.034 (4)0.001 (3)0.010 (3)
C170.061 (3)0.085 (4)0.063 (3)0.007 (3)0.005 (2)0.023 (3)
C180.051 (2)0.050 (2)0.056 (3)0.008 (2)0.010 (2)0.007 (2)
C190.043 (2)0.057 (3)0.058 (3)0.001 (2)0.003 (2)0.010 (2)
C200.057 (3)0.090 (4)0.080 (4)0.010 (3)0.008 (3)0.011 (3)
C210.061 (3)0.087 (4)0.085 (4)0.014 (3)0.008 (3)0.019 (3)
C220.056 (3)0.052 (2)0.046 (2)0.006 (2)0.0112 (19)0.012 (2)
C230.072 (3)0.062 (3)0.054 (3)0.016 (2)0.010 (2)0.005 (2)
C240.085 (4)0.080 (4)0.058 (3)0.009 (3)0.013 (3)0.003 (3)
C250.120 (5)0.081 (4)0.042 (3)0.012 (4)0.004 (3)0.004 (3)
C260.144 (6)0.075 (4)0.055 (3)0.025 (4)0.010 (4)0.010 (3)
C270.085 (4)0.077 (4)0.058 (3)0.030 (3)0.011 (3)0.004 (3)
C280.042 (2)0.075 (3)0.067 (3)0.007 (2)0.002 (2)0.019 (2)
C290.055 (3)0.070 (3)0.066 (3)0.014 (2)0.001 (2)0.007 (2)
C300.113 (5)0.084 (4)0.081 (4)0.013 (4)0.018 (3)0.016 (3)
C310.075 (4)0.119 (5)0.098 (4)0.040 (3)0.022 (3)0.027 (4)
C320.047 (3)0.060 (3)0.075 (3)0.019 (2)0.004 (2)0.012 (2)
C330.066 (3)0.090 (4)0.081 (4)0.022 (3)0.011 (3)0.016 (3)
C340.105 (5)0.131 (6)0.087 (5)0.056 (5)0.023 (4)0.009 (4)
C350.116 (6)0.122 (6)0.089 (5)0.070 (5)0.027 (4)0.051 (5)
C360.093 (5)0.084 (5)0.132 (6)0.036 (4)0.028 (4)0.056 (5)
C370.062 (3)0.058 (3)0.110 (5)0.017 (3)0.002 (3)0.019 (3)
Geometric parameters (Å, º) top
Sn1—O12.109 (3)C17—H17A0.9300
Sn1—C182.144 (4)C18—C191.536 (6)
Sn1—C82.146 (4)C18—H18A0.9700
Sn1—C282.147 (4)C18—H18B0.9700
N1—O41.185 (5)C19—C221.524 (6)
N1—O31.194 (5)C19—C201.533 (6)
N1—C41.459 (5)C19—C211.549 (6)
N2—O61.198 (5)C20—H20A0.9600
N2—O51.205 (5)C20—H20B0.9600
N2—C61.470 (5)C20—H20C0.9600
O1—C11.273 (5)C21—H21A0.9600
O2—C11.242 (5)C21—H21B0.9600
O7A—C31.326 (5)C21—H21C0.9600
O7A—H7AA0.8200C22—C231.389 (6)
O7B—C71.393 (17)C22—C271.392 (6)
O7B—H7BA0.8200C23—C241.370 (6)
C1—C21.479 (5)C23—H23A0.9300
C2—C71.394 (5)C24—C251.373 (7)
C2—C31.405 (5)C24—H24A0.9300
C3—C41.391 (5)C25—C261.357 (8)
C3—H3A0.9300C25—H25A0.9300
C4—C51.381 (5)C26—C271.371 (7)
C5—C61.364 (6)C26—H26A0.9300
C5—H5A0.9300C27—H27A0.9300
C6—C71.377 (5)C28—C291.544 (6)
C7—H7A0.9300C28—H28A0.9700
C8—C91.529 (6)C28—H28B0.9700
C8—H8A0.9700C29—C321.524 (6)
C8—H8B0.9700C29—C301.525 (7)
C9—C111.512 (7)C29—C311.549 (6)
C9—C121.522 (6)C30—H30A0.9600
C9—C101.547 (8)C30—H30B0.9600
C10—H10A0.9600C30—H30C0.9600
C10—H10B0.9600C31—H31A0.9600
C10—H10C0.9600C31—H31B0.9600
C11—H11A0.9600C31—H31C0.9600
C11—H11B0.9600C32—C331.372 (7)
C11—H11C0.9600C32—C371.389 (6)
C12—C171.363 (6)C33—C341.392 (7)
C12—C131.381 (6)C33—H33A0.9300
C13—C141.359 (7)C34—C351.385 (9)
C13—H13A0.9300C34—H34A0.9300
C14—C151.350 (8)C35—C361.340 (10)
C14—H14A0.9300C35—H35A0.9300
C15—C161.345 (8)C36—C371.366 (8)
C15—H15A0.9300C36—H36A0.9300
C16—C171.389 (7)C37—H37A0.9300
C16—H16A0.9300
O1—Sn1—C18104.07 (14)C19—C18—H18A108.1
O1—Sn1—C8101.84 (15)Sn1—C18—H18A108.1
C18—Sn1—C8116.22 (16)C19—C18—H18B108.1
O1—Sn1—C2890.41 (15)Sn1—C18—H18B108.1
C18—Sn1—C28118.70 (17)H18A—C18—H18B107.3
C8—Sn1—C28118.25 (17)C22—C19—C20112.9 (4)
O4—N1—O3122.6 (4)C22—C19—C18111.3 (3)
O4—N1—C4117.3 (4)C20—C19—C18108.7 (4)
O3—N1—C4120.0 (4)C22—C19—C21107.2 (4)
O6—N2—O5124.2 (5)C20—C19—C21108.4 (4)
O6—N2—C6117.9 (4)C18—C19—C21108.2 (4)
O5—N2—C6117.9 (5)C19—C20—H20A109.5
C1—O1—Sn1119.9 (3)C19—C20—H20B109.5
C3—O7A—H7AA109.5H20A—C20—H20B109.5
C7—O7B—H7BA109.5C19—C20—H20C109.5
O2—C1—O1123.1 (4)H20A—C20—H20C109.5
O2—C1—C2120.0 (4)H20B—C20—H20C109.5
O1—C1—C2116.9 (4)C19—C21—H21A109.5
C7—C2—C3119.9 (3)C19—C21—H21B109.5
C7—C2—C1120.6 (4)H21A—C21—H21B109.5
C3—C2—C1119.5 (3)C19—C21—H21C109.5
O7A—C3—C4121.4 (4)H21A—C21—H21C109.5
O7A—C3—C2119.8 (4)H21B—C21—H21C109.5
C4—C3—C2118.7 (3)C23—C22—C27115.8 (5)
C4—C3—H3A120.6C23—C22—C19121.1 (4)
C2—C3—H3A120.6C27—C22—C19123.1 (4)
C5—C4—C3121.1 (4)C24—C23—C22122.4 (4)
C5—C4—N1117.6 (4)C24—C23—H23A118.8
C3—C4—N1121.4 (4)C22—C23—H23A118.8
C6—C5—C4119.1 (4)C23—C24—C25120.2 (5)
C6—C5—H5A120.4C23—C24—H24A119.9
C4—C5—H5A120.4C25—C24—H24A119.9
C5—C6—C7122.1 (4)C26—C25—C24118.6 (5)
C5—C6—N2118.2 (4)C26—C25—H25A120.7
C7—C6—N2119.7 (4)C24—C25—H25A120.7
C6—C7—O7B120.1 (8)C25—C26—C27121.5 (5)
C6—C7—C2119.0 (4)C25—C26—H26A119.3
O7B—C7—C2120.8 (8)C27—C26—H26A119.3
C6—C7—H7A120.5C26—C27—C22121.5 (5)
C2—C7—H7A120.5C26—C27—H27A119.3
C9—C8—Sn1118.3 (3)C22—C27—H27A119.3
C9—C8—H8A107.7C29—C28—Sn1119.7 (3)
Sn1—C8—H8A107.7C29—C28—H28A107.4
C9—C8—H8B107.7Sn1—C28—H28A107.4
Sn1—C8—H8B107.7C29—C28—H28B107.4
H8A—C8—H8B107.1Sn1—C28—H28B107.4
C11—C9—C12111.9 (5)H28A—C28—H28B106.9
C11—C9—C8108.1 (4)C32—C29—C30113.1 (4)
C12—C9—C8111.3 (4)C32—C29—C28109.1 (4)
C11—C9—C10108.8 (5)C30—C29—C28109.5 (4)
C12—C9—C10107.7 (4)C32—C29—C31109.2 (4)
C8—C9—C10108.9 (4)C30—C29—C31108.2 (4)
C9—C10—H10A109.5C28—C29—C31107.5 (4)
C9—C10—H10B109.5C29—C30—H30A109.5
H10A—C10—H10B109.5C29—C30—H30B109.5
C9—C10—H10C109.5H30A—C30—H30B109.5
H10A—C10—H10C109.5C29—C30—H30C109.5
H10B—C10—H10C109.5H30A—C30—H30C109.5
C9—C11—H11A109.5H30B—C30—H30C109.5
C9—C11—H11B109.5C29—C31—H31A109.5
H11A—C11—H11B109.5C29—C31—H31B109.5
C9—C11—H11C109.5H31A—C31—H31B109.5
H11A—C11—H11C109.5C29—C31—H31C109.5
H11B—C11—H11C109.5H31A—C31—H31C109.5
C17—C12—C13116.7 (4)H31B—C31—H31C109.5
C17—C12—C9118.9 (4)C33—C32—C37117.4 (5)
C13—C12—C9124.3 (4)C33—C32—C29119.5 (5)
C14—C13—C12121.8 (5)C37—C32—C29123.1 (5)
C14—C13—H13A119.1C32—C33—C34121.6 (6)
C12—C13—H13A119.1C32—C33—H33A119.2
C15—C14—C13120.6 (6)C34—C33—H33A119.2
C15—C14—H14A119.7C35—C34—C33119.0 (7)
C13—C14—H14A119.7C35—C34—H34A120.5
C16—C15—C14119.5 (6)C33—C34—H34A120.5
C16—C15—H15A120.3C36—C35—C34119.4 (7)
C14—C15—H15A120.3C36—C35—H35A120.3
C15—C16—C17120.3 (5)C34—C35—H35A120.3
C15—C16—H16A119.8C35—C36—C37121.9 (7)
C17—C16—H16A119.8C35—C36—H36A119.1
C12—C17—C16121.1 (5)C37—C36—H36A119.1
C12—C17—H17A119.4C36—C37—C32120.7 (6)
C16—C17—H17A119.4C36—C37—H37A119.7
C19—C18—Sn1116.7 (3)C32—C37—H37A119.7
C18—Sn1—O1—C168.1 (3)C17—C12—C13—C140.9 (7)
C8—Sn1—O1—C153.1 (3)C9—C12—C13—C14178.8 (5)
C28—Sn1—O1—C1172.1 (3)C12—C13—C14—C150.4 (9)
Sn1—O1—C1—O212.5 (6)C13—C14—C15—C160.9 (9)
Sn1—O1—C1—C2167.4 (3)C14—C15—C16—C170.1 (9)
O2—C1—C2—C7177.7 (4)C13—C12—C17—C161.7 (7)
O1—C1—C2—C72.2 (6)C9—C12—C17—C16178.0 (5)
O2—C1—C2—C32.5 (6)C15—C16—C17—C121.2 (9)
O1—C1—C2—C3177.7 (4)O1—Sn1—C18—C19128.6 (3)
C7—C2—C3—O7A176.2 (4)C8—Sn1—C18—C1917.5 (4)
C1—C2—C3—O7A3.9 (6)C28—Sn1—C18—C19133.1 (3)
C7—C2—C3—C43.1 (5)Sn1—C18—C19—C2247.0 (4)
C1—C2—C3—C4176.7 (3)Sn1—C18—C19—C2077.9 (4)
O7A—C3—C4—C5177.1 (4)Sn1—C18—C19—C21164.6 (3)
C2—C3—C4—C52.3 (6)C20—C19—C22—C23159.5 (4)
O7A—C3—C4—N13.3 (6)C18—C19—C22—C2337.0 (5)
C2—C3—C4—N1177.3 (4)C21—C19—C22—C2381.2 (5)
O4—N1—C4—C53.5 (7)C20—C19—C22—C2722.0 (6)
O3—N1—C4—C5178.0 (4)C18—C19—C22—C27144.5 (4)
O4—N1—C4—C3177.0 (5)C21—C19—C22—C2797.3 (5)
O3—N1—C4—C31.6 (6)C27—C22—C23—C240.2 (7)
C3—C4—C5—C60.1 (6)C19—C22—C23—C24178.5 (4)
N1—C4—C5—C6179.7 (4)C22—C23—C24—C250.1 (8)
C4—C5—C6—C71.7 (6)C23—C24—C25—C260.5 (8)
C4—C5—C6—N2179.3 (4)C24—C25—C26—C271.1 (9)
O6—N2—C6—C5164.1 (5)C25—C26—C27—C221.2 (9)
O5—N2—C6—C515.0 (6)C23—C22—C27—C260.7 (7)
O6—N2—C6—C717.0 (6)C19—C22—C27—C26177.9 (5)
O5—N2—C6—C7163.9 (4)O1—Sn1—C28—C2991.6 (4)
C5—C6—C7—O7B178.0 (10)C18—Sn1—C28—C2914.7 (4)
N2—C6—C7—O7B0.9 (11)C8—Sn1—C28—C29164.7 (3)
C5—C6—C7—C20.9 (6)Sn1—C28—C29—C3271.8 (5)
N2—C6—C7—C2179.8 (4)Sn1—C28—C29—C3052.5 (5)
C3—C2—C7—C61.6 (6)Sn1—C28—C29—C31169.9 (3)
C1—C2—C7—C6178.2 (4)C30—C29—C32—C33177.6 (4)
C3—C2—C7—O7B179.5 (10)C28—C29—C32—C3360.3 (5)
C1—C2—C7—O7B0.6 (11)C31—C29—C32—C3357.0 (6)
O1—Sn1—C8—C996.0 (3)C30—C29—C32—C372.7 (6)
C18—Sn1—C8—C9151.7 (3)C28—C29—C32—C37119.5 (5)
C28—Sn1—C8—C90.9 (4)C31—C29—C32—C37123.3 (5)
Sn1—C8—C9—C1174.3 (5)C37—C32—C33—C340.9 (7)
Sn1—C8—C9—C1249.0 (5)C29—C32—C33—C34178.9 (4)
Sn1—C8—C9—C10167.6 (4)C32—C33—C34—C350.4 (8)
C11—C9—C12—C17171.3 (5)C33—C34—C35—C360.9 (9)
C8—C9—C12—C1750.3 (6)C34—C35—C36—C370.1 (10)
C10—C9—C12—C1769.1 (6)C35—C36—C37—C321.2 (8)
C11—C9—C12—C138.4 (7)C33—C32—C37—C361.7 (7)
C8—C9—C12—C13129.4 (5)C29—C32—C37—C36178.1 (4)
C10—C9—C12—C13111.2 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7B—H7BA···O10.821.742.465 (18)147
O7A—H7AA···O20.821.732.477 (4)150

Experimental details

Crystal data
Chemical formula[Sn(C10H13)3(C7H3N2O7)]
Mr745.42
Crystal system, space groupMonoclinic, P21/n
Temperature (K)295
a, b, c (Å)10.0060 (8), 22.6236 (18), 15.8991 (13)
β (°) 95.512 (1)
V3)3582.5 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.76
Crystal size (mm)0.25 × 0.10 × 0.08
Data collection
DiffractometerBruker APEX area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.832, 0.942
No. of measured, independent and
observed [I > 2σ(I)] reflections
26672, 6649, 5673
Rint0.040
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.110, 1.18
No. of reflections6649
No. of parameters434
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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—O12.109 (3)O2—C11.242 (5)
Sn1—C182.144 (4)O7A—C31.326 (5)
Sn1—C82.146 (4)O7B—C71.393 (17)
Sn1—C282.147 (4)C1—C21.479 (5)
O1—C11.273 (5)
O1—Sn1—C18104.07 (14)O1—Sn1—C2890.41 (15)
O1—Sn1—C8101.84 (15)C18—Sn1—C28118.70 (17)
C18—Sn1—C8116.22 (16)C8—Sn1—C28118.25 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7B—H7BA···O10.821.742.465 (18)147
O7A—H7AA···O20.821.732.477 (4)150
 

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