2-(Ethoxy­carbon­yl)quinolinium butyl­trichlorido(quinoline-2-carboxyl­ato-κ2N,O)stannate(IV)

Wang, H.; Yin, H.; Sun, Y.

doi:10.1107/S1600536807067566

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page m272

doi:10.1107/S1600536807067566

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2-(Ethoxycarbonyl)quinolinium butyltrichlorido(quinoline-2-carboxylato-κ²N,O)stannate(IV)

Hongyun Wang,^a Handong Yin ^a ^* and Yuying Sun ^b

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China, and ^bAnalytical and Testing Center of Beihua University, 132013, People's Republic of China
^*Correspondence e-mail: handongyin@163.com

(Received 18 November 2007; accepted 18 December 2007; online 4 January 2008)

In the title compound, (C₁₂H₁₂NO₂)[Sn(C₄H₉)(C₁₀H₆NO₂)Cl₃], the Sn atom is coordinated by one O and one N atom of a quinolinium-2-carboxylate anion, three Cl atoms and one butyl ligand within a distorted octahedron. Three C atoms of the butyl ligand are disordered and were refined using a split model; the site occupancies are 0.57 and 0.43. The NH group of the cation is involved in intermolecular N—H⋯O hydrogen bonding.

Related literature

For related literature, see: Xie et al. (1991 ); Ma et al. (2006 ).

Experimental

Crystal data

(C₁₂H₁₂NO₂)[Sn(C₄H₉)(C₁₀H₆NO₂)Cl₃]
M_r = 656.54
Monoclinic, P 2₁ /c
a = 13.6828 (18) Å
b = 11.0449 (15) Å
c = 18.598 (2) Å
β = 93.898 (2)°
V = 2804.1 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.23 mm⁻¹
T = 293 (2) K
0.43 × 0.25 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.620, T_max = 0.876
13504 measured reflections
4942 independent reflections
2884 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.132
S = 1.00
4942 reflections
328 parameters
15 restraints
H-atom parameters constrained
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Sn1—O1	2.079 (4)
Sn1—C11	2.142 (7)
Sn1—N1	2.371 (4)
Sn1—Cl2	2.4405 (18)
Sn1—Cl3	2.4482 (18)
Sn1—Cl1	2.4924 (16)

O1—Sn1—C11	172.6 (2)
O1—Sn1—N1	73.06 (16)
C11—Sn1—N1	107.7 (3)
O1—Sn1—Cl2	82.66 (12)
C11—Sn1—Cl2	96.4 (3)
N1—Sn1—Cl2	155.72 (13)
O1—Sn1—Cl3	87.93 (13)
C11—Sn1—Cl3	99.5 (2)
N1—Sn1—Cl3	84.64 (12)
Cl2—Sn1—Cl3	94.28 (6)
O1—Sn1—Cl1	83.87 (13)
C11—Sn1—Cl1	88.8 (2)
N1—Sn1—Cl1	84.22 (12)
Cl2—Sn1—Cl1	93.73 (6)
Cl3—Sn1—Cl1	167.71 (6)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.86	2.26	3.078 (7)	158
N2—H2⋯O4ⁱ	0.86	2.53	2.990 (6)	114
Symmetry code: (i) -x+2, -y, -z+1.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807067566/nc2083sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807067566/nc2083Isup2.hkl

checkCIF report

Comment top

Organotin esters of carboxylic acids are widely used as biocidesand fungicides and in industry as homogeneous catalysts(Q. L. Xie et al., 1991). As a part of our ongoing investigations in this field we have synthesized the title compound and determined its crystal structure. The crystal structure of the title compound consists of discrete [ethyl(quinolinium-2-carboxylate)] cations and discrete [trichloro-butyl-(quinoline-2-carboxylato)tin(IV)] anions (Fig. 1 and Table 1). The Sn atom is coordinated by one O and one N atom of a quinolinium-2-carboxylate anion, which acts as a chelate ligand, three chloro atoms and one carbon atom of the butyl ligand within a distorted octahedral environment. The Sn1—O1 distance of 2.079 (4)Å and the Sn1—N1 distance of 2.371 (4) Å are comparable to those in similar organotin carboxylates (C. L. Ma et al., 2006). The N—H H atom of the [ethyl(quinolinium-2-carboxylate)] cation is involved in intermolecular N—H···O hydrogen bonding to O2 of the [ethyl(quinolinium-2-carboxylate)] anion (Table 2). The N—H atom forms an additional very weak hydrogen bond to O4 of a second [ethyl(quinolinium-2-carboxylate)] anion.

Related literature top

For related literature, see: Xie et al. (1991); Ma et al. (2006).

Experimental top

The reaction was carried out under nitrogen atmosphere. Quinoline-2-carboxylic acid (1 mmol) and sodium ethoxide (1.2 mmol) were added to the solution of ethanol (30 ml) in a Schlenk flask and stirred for 0.5 h. Butyltin trichloride (1 mmol) was added to the Schlenk flask and the reaction mixture was stirred for 12 h at 313 K.The solvent was removed from the clear under reduced pressure. The crew prodcut was recrystallized from a mixture of dichloromethane/methanol (1:1).(yield 76%; m.p. 466 K). Analysis calculated (%) for C₂₆H₂₇Cl₃N₂O₄Sn (Mr = 656.54): C, 47.56; H, 4.14; N, 4.27. found: C, 47.49; H, 4.21; N, 4.32.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top

Fig. 1. Crystal structure of the title compound with labeling and displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity and the two orientations of the disordered butyl ligand is shown as closed and open lines.

2-(Ethoxycarbonyl)quinolinium butyltrichlorido(quinoline-2-carboxylato-κ²N,O)tin(IV) top

Crystal data top

(C₁₂H₁₂NO₂)[Sn(C₄H₉)(C₁₀H₆NO₂)Cl₃]	F(000) = 1320
M_r = 656.54	D_x = 1.555 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.6828 (18) Å	Cell parameters from 2742 reflections
b = 11.0449 (15) Å	θ = 2.2–20.4°
c = 18.598 (2) Å	µ = 1.23 mm⁻¹
β = 93.898 (2)°	T = 293 K
V = 2804.1 (6) Å³	Block, colourless
Z = 4	0.43 × 0.25 × 0.11 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4942 independent reflections
Radiation source: fine-focus sealed tube	2884 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→12
T_min = 0.620, T_max = 0.877	k = −13→13
13504 measured reflections	l = −18→22

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.064P)²] where P = (F_o² + 2F_c²)/3
4942 reflections	(Δ/σ)_max < 0.001
328 parameters	Δρ_max = 0.64 e Å⁻³
15 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

(C₁₂H₁₂NO₂)[Sn(C₄H₉)(C₁₀H₆NO₂)Cl₃]	V = 2804.1 (6) Å³
M_r = 656.54	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.6828 (18) Å	µ = 1.23 mm⁻¹
b = 11.0449 (15) Å	T = 293 K
c = 18.598 (2) Å	0.43 × 0.25 × 0.11 mm
β = 93.898 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4942 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2884 reflections with I > 2σ(I)
T_min = 0.620, T_max = 0.877	R_int = 0.050
13504 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	15 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.00	Δρ_max = 0.64 e Å⁻³
4942 reflections	Δρ_min = −0.41 e Å⁻³
328 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sn1	0.69831 (3)	0.03081 (4)	0.28168 (2)	0.04929 (18)
Cl1	0.74131 (13)	−0.15041 (15)	0.35719 (8)	0.0612 (5)
Cl2	0.82158 (17)	−0.01177 (16)	0.19623 (10)	0.0823 (7)
Cl3	0.65882 (15)	0.23171 (16)	0.23224 (10)	0.0769 (6)
O1	0.8168 (3)	0.1091 (4)	0.3402 (2)	0.0581 (12)
O2	0.8843 (4)	0.1604 (5)	0.4467 (3)	0.0805 (15)
N1	0.6386 (4)	0.1089 (4)	0.3890 (2)	0.0458 (12)
C1	0.8125 (5)	0.1382 (5)	0.4063 (4)	0.0512 (16)
C2	0.7123 (5)	0.1434 (5)	0.4343 (3)	0.0470 (15)
C3	0.6989 (6)	0.1831 (6)	0.5037 (3)	0.0617 (18)
H3	0.7526	0.2064	0.5339	0.074*
C4	0.6076 (6)	0.1880 (6)	0.5275 (4)	0.072 (2)
H4	0.5983	0.2139	0.5742	0.087*
C5	0.5276 (5)	0.1540 (6)	0.4815 (4)	0.0591 (18)
C6	0.5443 (5)	0.1167 (5)	0.4111 (3)	0.0497 (16)
C7	0.4649 (5)	0.0865 (7)	0.3630 (4)	0.076 (2)
H7	0.4755	0.0634	0.3161	0.092*
C8	0.3722 (6)	0.0909 (8)	0.3852 (5)	0.093 (3)
H8	0.3195	0.0703	0.3533	0.112*
C9	0.3554 (7)	0.1265 (8)	0.4561 (6)	0.093 (3)
H9	0.2921	0.1281	0.4714	0.111*
C10	0.4302 (7)	0.1574 (7)	0.5005 (5)	0.082 (3)
H10	0.4178	0.1827	0.5468	0.099*
C11	0.5827 (6)	−0.0718 (7)	0.2273 (4)	0.093 (3)
H11A	0.6106	−0.1407	0.2037	0.111*	0.57
H11B	0.5396	−0.1023	0.2625	0.111*	0.57
H11C	0.6017	−0.1564	0.2288	0.111*	0.43
H11D	0.5249	−0.0640	0.2544	0.111*	0.43
C12	0.5211 (17)	0.0064 (16)	0.1694 (10)	0.120 (6)*	0.57
H12A	0.4823	0.0644	0.1943	0.144*	0.57
H12B	0.5659	0.0516	0.1414	0.144*	0.57
C13	0.4535 (16)	−0.0666 (17)	0.1185 (10)	0.144 (7)*	0.57
H13A	0.3999	−0.1010	0.1433	0.173*	0.57
H13B	0.4887	−0.1313	0.0962	0.173*	0.57
C14	0.4166 (18)	0.0265 (18)	0.0631 (12)	0.148 (9)*	0.57
H14A	0.3730	−0.0118	0.0274	0.222*	0.57
H14B	0.4712	0.0606	0.0402	0.222*	0.57
H14C	0.3824	0.0895	0.0865	0.222*	0.57
C12'	0.553 (2)	−0.038 (3)	0.1457 (10)	0.147 (12)*	0.43
H12C	0.5956	0.0233	0.1271	0.176*	0.43
H12D	0.5502	−0.1082	0.1143	0.176*	0.43
C13'	0.451 (2)	0.011 (3)	0.1610 (18)	0.196 (16)*	0.43
H13C	0.4580	0.0926	0.1803	0.235*	0.43
H13D	0.4235	−0.0390	0.1974	0.235*	0.43
C14'	0.379 (2)	0.014 (3)	0.0927 (17)	0.155 (13)*	0.43
H14D	0.3172	0.0466	0.1048	0.232*	0.43
H14E	0.3694	−0.0671	0.0746	0.232*	0.43
H14F	0.4057	0.0633	0.0564	0.232*	0.43
O3	1.0771 (3)	0.3148 (4)	0.5369 (2)	0.0624 (12)
O4	1.0959 (3)	0.1229 (4)	0.4993 (2)	0.0598 (12)
N2	0.9935 (4)	0.0470 (4)	0.6118 (2)	0.0461 (12)
H2	1.0216	−0.0030	0.5844	0.055*
C15	1.0645 (5)	0.1969 (6)	0.5387 (3)	0.0506 (16)
C16	1.0041 (4)	0.1641 (5)	0.5998 (3)	0.0429 (14)
C17	0.9592 (5)	0.2459 (6)	0.6425 (3)	0.0542 (17)
H17	0.9642	0.3284	0.6335	0.058 (18)*
C18	0.9077 (5)	0.2060 (6)	0.6975 (3)	0.0593 (18)
H18	0.8796	0.2622	0.7272	0.07 (2)*
C19	0.8962 (5)	0.0835 (5)	0.7110 (3)	0.0487 (15)
C20	0.9409 (5)	0.0006 (5)	0.6651 (3)	0.0473 (16)
C21	0.9317 (5)	−0.1241 (6)	0.6754 (3)	0.0571 (18)
H21	0.9631	−0.1785	0.6465	0.07 (2)*
C22	0.8756 (5)	−0.1650 (7)	0.7282 (4)	0.068 (2)
H22	0.8660	−0.2477	0.7337	0.08 (2)*
C23	0.8330 (6)	−0.0833 (7)	0.7743 (4)	0.072 (2)
H23	0.7978	−0.1129	0.8116	0.07 (2)*
C24	0.8416 (5)	0.0365 (7)	0.7658 (4)	0.067 (2)
H24	0.8115	0.0890	0.7966	0.10 (3)*
C25	1.1392 (6)	0.3627 (7)	0.4834 (4)	0.084 (2)
H25A	1.1096	0.3482	0.4353	0.101*
H25B	1.2028	0.3236	0.4876	0.101*
C26	1.1503 (7)	0.4927 (7)	0.4965 (5)	0.107 (3)
H26A	1.0869	0.5301	0.4945	0.161*
H26B	1.1884	0.5276	0.4603	0.161*
H26C	1.1829	0.5056	0.5432	0.161*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0565 (3)	0.0507 (3)	0.0415 (3)	0.0008 (2)	0.00965 (19)	−0.0027 (2)
Cl1	0.0690 (12)	0.0592 (10)	0.0573 (10)	0.0150 (9)	0.0176 (8)	0.0050 (8)
Cl2	0.1224 (18)	0.0624 (11)	0.0690 (11)	0.0002 (11)	0.0563 (12)	−0.0073 (9)
Cl3	0.0952 (16)	0.0634 (11)	0.0731 (12)	0.0124 (11)	0.0122 (10)	0.0132 (9)
O1	0.048 (3)	0.071 (3)	0.058 (3)	0.000 (2)	0.015 (2)	−0.012 (2)
O2	0.053 (3)	0.109 (4)	0.079 (3)	−0.004 (3)	−0.007 (3)	−0.020 (3)
N1	0.042 (3)	0.049 (3)	0.047 (3)	0.009 (3)	0.008 (2)	−0.005 (2)
C1	0.047 (4)	0.049 (4)	0.058 (4)	0.001 (3)	0.008 (3)	−0.004 (3)
C2	0.050 (4)	0.046 (4)	0.046 (4)	0.004 (3)	0.008 (3)	−0.004 (3)
C3	0.073 (5)	0.066 (5)	0.046 (4)	0.000 (4)	0.005 (4)	−0.009 (3)
C4	0.098 (7)	0.067 (5)	0.055 (4)	0.011 (5)	0.023 (5)	−0.017 (4)
C5	0.065 (5)	0.053 (4)	0.063 (4)	0.016 (4)	0.031 (4)	0.004 (3)
C6	0.047 (4)	0.053 (4)	0.052 (4)	0.009 (3)	0.017 (3)	0.009 (3)
C7	0.052 (5)	0.106 (6)	0.072 (5)	0.000 (5)	0.010 (4)	0.009 (4)
C8	0.042 (5)	0.129 (7)	0.107 (7)	0.008 (5)	0.002 (5)	0.038 (6)
C9	0.058 (6)	0.096 (7)	0.128 (8)	0.024 (5)	0.044 (6)	0.030 (6)
C10	0.080 (7)	0.068 (5)	0.105 (7)	0.027 (5)	0.047 (6)	0.016 (5)
C11	0.098 (7)	0.083 (5)	0.093 (6)	−0.010 (5)	−0.028 (5)	−0.015 (5)
O3	0.075 (3)	0.054 (3)	0.061 (3)	−0.003 (3)	0.027 (2)	0.011 (2)
O4	0.065 (3)	0.069 (3)	0.047 (3)	0.000 (3)	0.012 (2)	−0.009 (2)
N2	0.048 (3)	0.049 (3)	0.042 (3)	0.002 (3)	0.006 (2)	−0.004 (2)
C15	0.043 (4)	0.064 (5)	0.045 (4)	−0.004 (3)	0.002 (3)	0.006 (3)
C16	0.037 (4)	0.044 (4)	0.048 (4)	−0.001 (3)	0.007 (3)	0.004 (3)
C17	0.056 (4)	0.044 (4)	0.064 (4)	−0.001 (3)	0.020 (3)	0.007 (3)
C18	0.071 (5)	0.048 (4)	0.062 (4)	0.006 (4)	0.028 (4)	−0.001 (3)
C19	0.053 (4)	0.044 (4)	0.050 (4)	0.001 (3)	0.011 (3)	0.000 (3)
C20	0.049 (4)	0.048 (4)	0.045 (4)	−0.002 (3)	0.004 (3)	0.007 (3)
C21	0.070 (5)	0.044 (4)	0.057 (4)	−0.003 (4)	0.005 (4)	−0.003 (3)
C22	0.078 (6)	0.057 (5)	0.069 (5)	−0.009 (4)	0.003 (4)	0.012 (4)
C23	0.088 (6)	0.070 (5)	0.060 (5)	−0.006 (5)	0.023 (4)	0.018 (4)
C24	0.074 (5)	0.064 (5)	0.066 (5)	0.001 (4)	0.027 (4)	0.006 (4)
C25	0.100 (7)	0.072 (5)	0.087 (6)	−0.021 (5)	0.045 (5)	0.012 (4)
C26	0.127 (9)	0.102 (7)	0.098 (6)	−0.028 (6)	0.042 (6)	0.026 (5)

Geometric parameters (Å, º) top

Sn1—O1	2.079 (4)	C14—H14B	0.9600
Sn1—C11	2.142 (7)	C14—H14C	0.9600
Sn1—N1	2.371 (4)	C12'—C13'	1.547 (17)
Sn1—Cl2	2.4405 (18)	C12'—H12C	0.9700
Sn1—Cl3	2.4482 (18)	C12'—H12D	0.9700
Sn1—Cl1	2.4924 (16)	C13'—C14'	1.555 (17)
O1—C1	1.275 (7)	C13'—H13C	0.9700
O2—C1	1.221 (7)	C13'—H13D	0.9700
N1—C2	1.325 (7)	C14'—H14D	0.9600
N1—C6	1.383 (7)	C14'—H14E	0.9600
C1—C2	1.500 (8)	C14'—H14F	0.9600
C2—C3	1.386 (8)	O3—C15	1.315 (7)
C3—C4	1.355 (9)	O3—C25	1.452 (7)
C3—H3	0.9300	O4—C15	1.197 (7)
C4—C5	1.394 (10)	N2—C16	1.322 (7)
C4—H4	0.9300	N2—C20	1.363 (7)
C5—C10	1.403 (10)	N2—H2	0.8600
C5—C6	1.407 (8)	C15—C16	1.494 (8)
C6—C7	1.398 (9)	C16—C17	1.375 (8)
C7—C8	1.361 (10)	C17—C18	1.355 (8)
C7—H7	0.9300	C17—H17	0.9298
C8—C9	1.411 (11)	C18—C19	1.387 (8)
C8—H8	0.9300	C18—H18	0.9300
C9—C10	1.316 (11)	C19—C24	1.403 (8)
C9—H9	0.9300	C19—C20	1.419 (8)
C10—H10	0.9300	C20—C21	1.397 (8)
C11—C12	1.579 (13)	C21—C22	1.364 (8)
C11—C12'	1.587 (16)	C21—H21	0.9305
C11—H11A	0.9700	C22—C23	1.398 (9)
C11—H11B	0.9700	C22—H22	0.9295
C11—H11C	0.9700	C23—C24	1.339 (9)
C11—H11D	0.9700	C23—H23	0.9303
C12—C13	1.511 (14)	C24—H24	0.9306
C12—H12A	0.9700	C25—C26	1.463 (9)
C12—H12B	0.9700	C25—H25A	0.9699
C13—C14	1.518 (15)	C25—H25B	0.9699
C13—H13A	0.9700	C26—H26A	0.9600
C13—H13B	0.9700	C26—H26B	0.9600
C14—H14A	0.9600	C26—H26C	0.9600

O1—Sn1—C11	172.6 (2)	C14—C13—H13A	111.2
O1—Sn1—N1	73.06 (16)	C12—C13—H13B	111.2
C11—Sn1—N1	107.7 (3)	C14—C13—H13B	111.2
O1—Sn1—Cl2	82.66 (12)	H13A—C13—H13B	109.1
C11—Sn1—Cl2	96.4 (3)	C13—C14—H14A	109.5
N1—Sn1—Cl2	155.72 (13)	C13—C14—H14B	109.5
O1—Sn1—Cl3	87.93 (13)	H14A—C14—H14B	109.5
C11—Sn1—Cl3	99.5 (2)	C13—C14—H14C	109.5
N1—Sn1—Cl3	84.64 (12)	H14A—C14—H14C	109.5
Cl2—Sn1—Cl3	94.28 (6)	H14B—C14—H14C	109.5
O1—Sn1—Cl1	83.87 (13)	C13'—C12'—C11	94.6 (19)
C11—Sn1—Cl1	88.8 (2)	C13'—C12'—H12C	112.8
N1—Sn1—Cl1	84.22 (12)	C11—C12'—H12C	112.8
Cl2—Sn1—Cl1	93.73 (6)	C13'—C12'—H12D	112.8
Cl3—Sn1—Cl1	167.71 (6)	C11—C12'—H12D	112.8
C1—O1—Sn1	121.6 (4)	H12C—C12'—H12D	110.3
C2—N1—C6	118.7 (5)	C12'—C13'—C14'	113 (3)
C2—N1—Sn1	110.4 (4)	C12'—C13'—H13C	109.0
C6—N1—Sn1	130.8 (4)	C14'—C13'—H13C	109.0
O2—C1—O1	123.7 (6)	C12'—C13'—H13D	109.0
O2—C1—C2	119.7 (6)	C14'—C13'—H13D	109.0
O1—C1—C2	116.6 (6)	H13C—C13'—H13D	107.8
N1—C2—C3	122.6 (6)	C13'—C14'—H14D	109.5
N1—C2—C1	116.2 (5)	C13'—C14'—H14E	109.5
C3—C2—C1	121.2 (6)	H14D—C14'—H14E	109.5
C4—C3—C2	120.0 (7)	C13'—C14'—H14F	109.5
C4—C3—H3	120.0	H14D—C14'—H14F	109.5
C2—C3—H3	120.0	H14E—C14'—H14F	109.5
C3—C4—C5	119.4 (6)	C15—O3—C25	117.5 (5)
C3—C4—H4	120.3	C16—N2—C20	124.1 (5)
C5—C4—H4	120.3	C16—N2—H2	118.0
C4—C5—C10	123.9 (7)	C20—N2—H2	118.0
C4—C5—C6	118.8 (6)	O4—C15—O3	127.4 (6)
C10—C5—C6	117.3 (7)	O4—C15—C16	122.7 (6)
N1—C6—C7	119.7 (6)	O3—C15—C16	109.9 (6)
N1—C6—C5	120.5 (6)	N2—C16—C17	119.1 (5)
C7—C6—C5	119.8 (6)	N2—C16—C15	116.0 (5)
C8—C7—C6	119.8 (7)	C17—C16—C15	124.9 (6)
C8—C7—H7	120.1	C18—C17—C16	119.9 (6)
C6—C7—H7	120.1	C18—C17—H17	120.2
C7—C8—C9	120.5 (8)	C16—C17—H17	119.9
C7—C8—H8	119.8	C17—C18—C19	121.7 (6)
C9—C8—H8	119.8	C17—C18—H18	119.1
C10—C9—C8	119.4 (8)	C19—C18—H18	119.2
C10—C9—H9	120.3	C18—C19—C24	124.4 (6)
C8—C9—H9	120.3	C18—C19—C20	117.5 (6)
C9—C10—C5	123.1 (8)	C24—C19—C20	118.1 (6)
C9—C10—H10	118.4	N2—C20—C21	121.8 (6)
C5—C10—H10	118.4	N2—C20—C19	117.7 (5)
C12—C11—Sn1	112.1 (8)	C21—C20—C19	120.4 (6)
C12'—C11—Sn1	117.2 (12)	C22—C21—C20	119.1 (6)
C12—C11—H11A	109.2	C22—C21—H21	120.5
C12'—C11—H11A	80.4	C20—C21—H21	120.5
Sn1—C11—H11A	109.2	C21—C22—C23	120.4 (7)
C12—C11—H11B	109.2	C21—C22—H22	119.7
C12'—C11—H11B	126.9	C23—C22—H22	119.9
Sn1—C11—H11B	109.2	C24—C23—C22	121.5 (7)
H11A—C11—H11B	107.9	C24—C23—H23	119.3
C12—C11—H11C	132.5	C22—C23—H23	119.2
C12'—C11—H11C	107.6	C23—C24—C19	120.4 (7)
Sn1—C11—H11C	108.0	C23—C24—H24	119.8
H11B—C11—H11C	79.6	C19—C24—H24	119.8
C12—C11—H11D	83.6	O3—C25—C26	107.6 (6)
C12'—C11—H11D	108.3	O3—C25—H25A	110.2
Sn1—C11—H11D	108.0	C26—C25—H25A	110.3
H11A—C11—H11D	131.6	O3—C25—H25B	110.3
H11C—C11—H11D	107.3	C26—C25—H25B	110.0
C13—C12—C11	114.3 (14)	H25A—C25—H25B	108.5
C13—C12—H12A	108.7	C25—C26—H26A	109.5
C11—C12—H12A	108.7	C25—C26—H26B	109.5
C13—C12—H12B	108.7	H26A—C26—H26B	109.5
C11—C12—H12B	108.7	C25—C26—H26C	109.5
H12A—C12—H12B	107.6	H26A—C26—H26C	109.5
C12—C13—C14	103.0 (16)	H26B—C26—H26C	109.5
C12—C13—H13A	111.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.86	2.26	3.078 (7)	158
N2—H2···O4ⁱ	0.86	2.53	2.990 (6)	114

Symmetry code: (i) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	(C₁₂H₁₂NO₂)[Sn(C₄H₉)(C₁₀H₆NO₂)Cl₃]
M_r	656.54
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.6828 (18), 11.0449 (15), 18.598 (2)
β (°)	93.898 (2)
V (Å³)	2804.1 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.23
Crystal size (mm)	0.43 × 0.25 × 0.11

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.620, 0.877
No. of measured, independent and observed [I > 2σ(I)] reflections	13504, 4942, 2884
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.132, 1.00
No. of reflections	4942
No. of parameters	328
No. of restraints	15
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.41

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Selected geometric parameters (Å, º) top

Sn1—O1	2.079 (4)	Sn1—Cl2	2.4405 (18)
Sn1—C11	2.142 (7)	Sn1—Cl3	2.4482 (18)
Sn1—N1	2.371 (4)	Sn1—Cl1	2.4924 (16)

O1—Sn1—C11	172.6 (2)	N1—Sn1—Cl3	84.64 (12)
O1—Sn1—N1	73.06 (16)	Cl2—Sn1—Cl3	94.28 (6)
C11—Sn1—N1	107.7 (3)	O1—Sn1—Cl1	83.87 (13)
O1—Sn1—Cl2	82.66 (12)	C11—Sn1—Cl1	88.8 (2)
C11—Sn1—Cl2	96.4 (3)	N1—Sn1—Cl1	84.22 (12)
N1—Sn1—Cl2	155.72 (13)	Cl2—Sn1—Cl1	93.73 (6)
O1—Sn1—Cl3	87.93 (13)	Cl3—Sn1—Cl1	167.71 (6)
C11—Sn1—Cl3	99.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.86	2.26	3.078 (7)	158.4
N2—H2···O4ⁱ	0.86	2.53	2.990 (6)	114.2

Symmetry code: (i) −x+2, −y, −z+1.

Acknowledgements

We thank the National Natural Science Foundation of China (20771053) and the Natural Science Foundation of Shandong Province (2005ZX09) for financial support.

References

Ma, C. L., Li, J. K., Zhang, R. F. & Wang, D. Q. (2006). J. Organomet. Chem. 691, 1713–1721. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997a). SHELXL97 and SHELXS97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997b). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Xie, Q. L., Li, S. H., Zhang, D. K., Zhang, Z. G. & Hu, J. M. (1991). Acta Chim. Sinica, 49, 723–728. CAS Google Scholar

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