Dibut­yl[N-(5-chloro-2-oxidobenzyl­idene)-l-isoleucinato-κ3O,N,O′]tin(IV)

Yang, H.-J.; Dang, Y.-Q.

doi:10.1107/S1600536809039245

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page m1304

https://doi.org/10.1107/S1600536809039245

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Dibutyl[N-(5-chloro-2-oxidobenzylidene)-L-isoleucinato-κ³O,N,O′]tin(IV)

Hong-Jun Yang ^a and Yan-Qiu Dang ^b ^*

^aResearch Center for Eco-Environmental Sciences Yellow River Delta, Binzhou University, Binzhou 256600, People's Republic of China, and ^bDepartment of Chemistry & Chemical Engineering, Binzhou University, Binzhou 256600, People's Republic of China
^*Correspondence e-mail: yanqiudang@163.com

(Received 7 September 2009; accepted 27 September 2009; online 3 October 2009)

The Sn^IV atom of the title compound, [Sn(C₄H₉)₂(C₁₃H₁₄ClNO₃)], adopts a distorted SnNC₂O₂ trigonal-bipyramidal geometry with a mean Sn—C distance of 2.105 Å and with Sn—O = 2.107 Å, and forms five- and six-membered chelate rings with the tridentate ligand. One butyl group is disordered over two positions with site occupancies of 0.65 (1):0.35 (1).

Related literature

For the structures and biological activity of diorganotin complexes with Schiff bases derived from α-amino acids, see: Baul et al. (2007 ); Beltran et al. (2003 ); Dakternieks et al. (1998 ); Tian et al. (2004 , 2006 , 2007 , 2009 ).

Experimental

Crystal data

[Sn(C₄H₉)₂(C₁₃H₁₄ClNO₃)]
M_r = 500.62
Orthorhombic, P 2₁ 2₁ 2₁
a = 10.0545 (14) Å
b = 14.497 (2) Å
c = 15.953 (2) Å
V = 2325.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.23 mm⁻¹
T = 295 K
0.35 × 0.22 × 0.08 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.672, T_max = 0.908
18112 measured reflections
4574 independent reflections
3846 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.097
S = 1.05
4574 reflections
257 parameters
40 restraints
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.54 e Å⁻³
Absolute structure: Flack (1983 ), 1978 Friedel pairs
Flack parameter: 0.00 (4)

Table 1
Selected bond lengths (Å)

Sn1—O1	2.083 (3)
Sn1—C14	2.100 (6)
Sn1—C18	2.110 (6)
Sn1—O2	2.130 (3)
Sn1—N1	2.169 (3)

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809039245/hg2563sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809039245/hg2563Isup2.hkl

checkCIF report

Comment top

The diorganotin complexes with Schiff bases derived from α-amino acids continue to received attention because of their structural diversity and biological activities (Beltran et al., 2003; Basu Baul et al., 2007; Dakternieks et al., 1998; Tian et al., 2004, 2006, 2007, 2009). The structures of the diorganotin complexes based on the Schiff base ligand [N-(2-hydroxyphenylmethylene)isoleucine, [N-(2-oxidophenylmethylene)isoleucinato]dibutyltin (Beltran et al., 2003) and [N-(5-chloro-2-oxidophenylmethylene)isoleucinato]dicyclohexyltin (Tian et al., 2004) have been reported. As a continuation of these studies, the structure of the title compound, (I), is here described.

The coordination geometry of the tin atom in (I) is that of a distorted trigonal bipyramid with two butyl groups (C14 and C17) and the imino N1 atom occupying the equatorial positions and the axial positions being occupied by a unidentate carboxylate O2 atom and a phenoxide O1 atom (Fig. 1). The tin atom is 0.033 (3) Å out of the NC2 trigonal plane in the direction of the O1 atom. The bond length of Sn1—O1 (2.083 (6) Å) was shorter than that of Sn1—O2 (2.130 (3) Å). The bond angle O1—Sn1—O2 was 158.65 (13) °, which is slightly larger than that found in [N-(2-oxidophenylmethylene)isoleucinato]dibutyltin (154.5 (3)°) (Beltran et al., 2003) and [N-(5-chloro-2-oxidophenylmethylene)isoleucinato]dicyclohexyltin (153.84 (12)°) (Tian et al., 2004). Distortions from the ideal geometry may be rationalized partly by the restricted bite angles of the tridentate ligand. Neither of the five or six-membered rings formed upon chelation are planar, as seen in the following torsion angles: Sn1—O2—C9—C8 9.5 (6)°, Sn1—N1—C8—C9 13.4 (4)°, Sn1—O1—C1—C6 - 14.7 (7)° and Sn1—N1—C7—C6 10.4 (7)°.

Related literature top

For the structures and biological activity of diorganotin complexes with Schiff bases derived from α-amino acids, see: Basu Baul et al. (2007); Beltran et al. (2003); Dakternieks et al. (1998); Tian et al. (2004, 2006, 2007, 2009).

Experimental top

The title compound was prepared by the reaction of dibutyltin oxide (0.498 g, 2 mmol), L-isoleucine (0.262 g, 2 mmol) and 5-chlorosalicylaldehyde (0.314 g, 2 mmol) in 60 ml of benzene were refluxed for 8 h with azeotropic removal of water via a Dean-Stark trap. The resulting clear solution was evaporated under vacuum and the yellow crystalline material obtained was recrystallized from methanol. The product (yield 68%, m.p. 378–379 K) was then dissolved in dichloromethane-hexane (1:1, V/V), and yellow crystals were grown by slow evaporation.

Structure description top

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The structure of (I) with displacement ellipsoids are drawn at the 30% probability level. The minor disordered component of C14—C17 atoms of the butyl group and the H atoms have been omitted for clarity.

Dibutyl[N-(5-chloro-2-oxidobenzylidene)-L-isoleucinato- κ³O,N,O']tin(IV) top

Crystal data top

[Sn(C₄H₉)₂(C₁₃H₁₄ClNO₃)]	F(000) = 1024
M_r = 500.62	D_x = 1.430 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5601 reflections
a = 10.0545 (14) Å	θ = 2.4–23.1°
b = 14.497 (2) Å	µ = 1.23 mm⁻¹
c = 15.953 (2) Å	T = 295 K
V = 2325.3 (5) Å³	Block, yellow
Z = 4	0.35 × 0.22 × 0.08 mm

Data collection top

Bruker SMART APEX area-detector diffractometer	4574 independent reflections
Radiation source: fine-focus sealed tube	3846 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
φ and ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −12→12
T_min = 0.672, T_max = 0.908	k = −17→17
18112 measured reflections	l = −19→19

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.097	w = 1/[σ²(F_o²) + (0.0474P)² + 0.7356P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
4574 reflections	Δρ_max = 0.51 e Å⁻³
257 parameters	Δρ_min = −0.54 e Å⁻³
40 restraints	Absolute structure: Flack (1983), 1978 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (4)

Crystal data top

[Sn(C₄H₉)₂(C₁₃H₁₄ClNO₃)]	V = 2325.3 (5) Å³
M_r = 500.62	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.0545 (14) Å	µ = 1.23 mm⁻¹
b = 14.497 (2) Å	T = 295 K
c = 15.953 (2) Å	0.35 × 0.22 × 0.08 mm

Data collection top

Bruker SMART APEX area-detector diffractometer	4574 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	3846 reflections with I > 2σ(I)
T_min = 0.672, T_max = 0.908	R_int = 0.036
18112 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.097	Δρ_max = 0.51 e Å⁻³
S = 1.05	Δρ_min = −0.54 e Å⁻³
4574 reflections	Absolute structure: Flack (1983), 1978 Friedel pairs
257 parameters	Absolute structure parameter: 0.00 (4)
40 restraints

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	0.57193 (3)	1.00258 (2)	0.124910 (18)	0.06021 (12)
Cl1	1.19119 (17)	0.83857 (14)	0.33475 (12)	0.1064 (6)
N1	0.6662 (4)	0.8684 (2)	0.1157 (2)	0.0487 (8)
O1	0.7029 (4)	1.0206 (2)	0.2248 (2)	0.0767 (10)
O2	0.4697 (4)	0.9344 (2)	0.0257 (2)	0.0687 (10)
O3	0.4602 (5)	0.8138 (3)	−0.0595 (2)	0.0863 (12)
C1	0.8139 (5)	0.9793 (3)	0.2452 (3)	0.0593 (12)
C2	0.8952 (5)	1.0175 (4)	0.3079 (3)	0.0662 (14)
H2	0.8713	1.0736	0.3320	0.079*
C3	1.0080 (5)	0.9745 (4)	0.3343 (3)	0.0731 (16)
H3	1.0598	1.0009	0.3762	0.088*
C4	1.0458 (5)	0.8911 (4)	0.2988 (3)	0.0634 (13)
C5	0.9727 (5)	0.8519 (4)	0.2370 (3)	0.0621 (12)
H5	1.0000	0.7967	0.2128	0.075*
C6	0.8562 (5)	0.8947 (3)	0.2100 (3)	0.0514 (11)
C7	0.7776 (5)	0.8442 (3)	0.1488 (3)	0.0501 (11)
H7	0.8119	0.7877	0.1314	0.060*
C8	0.6029 (5)	0.8014 (3)	0.0581 (3)	0.0531 (11)
H8	0.6717	0.7745	0.0220	0.064*
C9	0.5027 (5)	0.8536 (4)	0.0029 (3)	0.0633 (13)
C10	0.5359 (5)	0.7231 (3)	0.1087 (3)	0.0559 (11)
H10	0.6024	0.7005	0.1487	0.067*
C11	0.4186 (6)	0.7574 (4)	0.1604 (4)	0.0824 (16)
H11A	0.3504	0.7800	0.1236	0.124*
H11B	0.4475	0.8062	0.1968	0.124*
H11C	0.3838	0.7075	0.1935	0.124*
C12	0.4958 (6)	0.6414 (4)	0.0554 (4)	0.0749 (16)
H12A	0.4561	0.5951	0.0915	0.090*
H12B	0.4279	0.6614	0.0162	0.090*
C13	0.6054 (9)	0.5975 (5)	0.0073 (5)	0.127 (3)
H13A	0.6356	0.6391	−0.0356	0.191*
H13B	0.5737	0.5417	−0.0182	0.191*
H13C	0.6777	0.5835	0.0444	0.191*
C14	0.4069 (6)	1.0251 (5)	0.2030 (5)	0.109 (2)	0.650 (10)
H14A	0.3707	0.9668	0.2222	0.131*	0.650 (10)
H14B	0.4324	1.0614	0.2515	0.131*	0.650 (10)
C15	0.3044 (11)	1.0769 (11)	0.1505 (7)	0.129 (4)	0.650 (10)
H15A	0.3501	1.1236	0.1180	0.154*	0.650 (10)
H15B	0.2643	1.0339	0.1113	0.154*	0.650 (10)
C16	0.1960 (11)	1.1223 (10)	0.1995 (8)	0.121 (4)	0.650 (10)
H16A	0.2284	1.1804	0.2215	0.145*	0.650 (10)
H16B	0.1725	1.0834	0.2467	0.145*	0.650 (10)
C17	0.0742 (12)	1.1397 (14)	0.1476 (10)	0.127 (5)	0.650 (10)
H17A	0.0058	1.1657	0.1823	0.191*	0.650 (10)
H17B	0.0435	1.0826	0.1240	0.191*	0.650 (10)
H17C	0.0954	1.1820	0.1032	0.191*	0.650 (10)
C14'	0.4069 (6)	1.0251 (5)	0.2030 (5)	0.109 (2)	0.350 (10)
H14C	0.4107	0.9760	0.2443	0.131*	0.350 (10)
H14D	0.4273	1.0814	0.2331	0.131*	0.350 (10)
C15'	0.2619 (12)	1.0331 (14)	0.1803 (17)	0.129 (4)	0.350 (10)
H15C	0.2061	1.0219	0.2289	0.154*	0.350 (10)
H15D	0.2386	0.9893	0.1368	0.154*	0.350 (10)
C16'	0.2453 (19)	1.1319 (14)	0.1492 (18)	0.121 (4)	0.350 (10)
H16C	0.2594	1.1742	0.1954	0.145*	0.350 (10)
H16D	0.3121	1.1446	0.1068	0.145*	0.350 (10)
C17'	0.108 (2)	1.148 (2)	0.112 (2)	0.127 (5)	0.350 (10)
H17D	0.0937	1.2130	0.1052	0.191*	0.350 (10)
H17E	0.0419	1.1234	0.1494	0.191*	0.350 (10)
H17F	0.1018	1.1179	0.0589	0.191*	0.350 (10)
C18	0.6505 (7)	1.1061 (4)	0.0462 (4)	0.0822 (17)
H18A	0.5828	1.1232	0.0057	0.099*
H18B	0.6693	1.1601	0.0800	0.099*
C19	0.7719 (6)	1.0809 (4)	0.0003 (4)	0.0811 (17)
H19A	0.7537	1.0276	−0.0346	0.097*
H19B	0.8403	1.0637	0.0402	0.097*
C20	0.8236 (8)	1.1589 (5)	−0.0545 (5)	0.110 (2)
H20A	0.7520	1.1790	−0.0909	0.132*
H20B	0.8465	1.2104	−0.0185	0.132*
C21	0.9395 (8)	1.1372 (6)	−0.1067 (5)	0.131 (3)
H21A	1.0188	1.1411	−0.0735	0.197*
H21B	0.9447	1.1804	−0.1522	0.197*
H21C	0.9307	1.0758	−0.1287	0.197*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0721 (2)	0.05157 (17)	0.05693 (18)	0.00367 (19)	−0.00498 (14)	−0.0011 (2)
Cl1	0.0716 (10)	0.1423 (15)	0.1053 (12)	0.0123 (11)	−0.0282 (9)	−0.0046 (11)
N1	0.058 (2)	0.0482 (18)	0.0403 (19)	0.0012 (16)	−0.0024 (18)	−0.0085 (16)
O1	0.090 (3)	0.065 (2)	0.075 (2)	0.017 (2)	−0.019 (2)	−0.0294 (17)
O2	0.088 (3)	0.060 (2)	0.059 (2)	−0.0046 (19)	−0.0222 (18)	0.0044 (16)
O3	0.128 (3)	0.075 (2)	0.056 (2)	−0.027 (2)	−0.030 (2)	−0.0001 (19)
C1	0.064 (3)	0.062 (3)	0.052 (2)	−0.003 (2)	0.004 (2)	−0.011 (2)
C2	0.073 (3)	0.069 (3)	0.057 (3)	−0.004 (3)	0.000 (2)	−0.026 (2)
C3	0.067 (3)	0.104 (5)	0.048 (2)	−0.022 (3)	−0.003 (2)	−0.008 (3)
C4	0.051 (3)	0.084 (4)	0.056 (3)	−0.003 (2)	−0.001 (2)	−0.001 (3)
C5	0.061 (3)	0.071 (3)	0.054 (3)	0.000 (2)	0.002 (2)	−0.009 (2)
C6	0.055 (3)	0.058 (3)	0.041 (2)	−0.006 (2)	0.006 (2)	−0.009 (2)
C7	0.061 (3)	0.045 (2)	0.044 (2)	−0.004 (2)	0.005 (2)	−0.0067 (18)
C8	0.061 (3)	0.052 (2)	0.047 (2)	−0.006 (2)	0.001 (2)	−0.0088 (19)
C9	0.075 (3)	0.069 (3)	0.046 (3)	−0.024 (3)	−0.013 (2)	0.010 (2)
C10	0.068 (3)	0.050 (2)	0.050 (3)	−0.008 (2)	−0.008 (2)	0.0027 (19)
C11	0.094 (4)	0.077 (3)	0.076 (3)	−0.009 (3)	0.013 (3)	0.012 (3)
C12	0.090 (4)	0.057 (3)	0.079 (4)	−0.016 (3)	−0.002 (3)	−0.004 (3)
C13	0.142 (6)	0.089 (4)	0.152 (6)	−0.018 (5)	0.027 (5)	−0.046 (5)
C14	0.088 (4)	0.122 (5)	0.116 (5)	0.033 (4)	0.019 (4)	−0.017 (4)
C15	0.096 (6)	0.147 (9)	0.142 (8)	0.004 (6)	0.031 (6)	−0.001 (7)
C16	0.120 (7)	0.129 (7)	0.114 (8)	0.023 (6)	0.012 (6)	0.016 (6)
C17	0.116 (7)	0.133 (6)	0.134 (10)	−0.002 (6)	−0.017 (7)	−0.006 (7)
C14'	0.088 (4)	0.122 (5)	0.116 (5)	0.033 (4)	0.019 (4)	−0.017 (4)
C15'	0.096 (6)	0.147 (9)	0.142 (8)	0.004 (6)	0.031 (6)	−0.001 (7)
C16'	0.120 (7)	0.129 (7)	0.114 (8)	0.023 (6)	0.012 (6)	0.016 (6)
C17'	0.116 (7)	0.133 (6)	0.134 (10)	−0.002 (6)	−0.017 (7)	−0.006 (7)
C18	0.111 (5)	0.049 (3)	0.087 (4)	−0.009 (3)	−0.004 (4)	0.007 (3)
C19	0.089 (4)	0.072 (4)	0.082 (4)	−0.006 (3)	−0.002 (3)	0.002 (3)
C20	0.122 (6)	0.099 (5)	0.108 (5)	−0.007 (5)	0.022 (5)	0.019 (4)
C21	0.133 (7)	0.132 (7)	0.129 (7)	−0.015 (5)	0.038 (6)	0.016 (5)

Geometric parameters (Å, º) top

Sn1—O1	2.083 (3)	C13—H13B	0.9600
Sn1—C14	2.100 (6)	C13—H13C	0.9600
Sn1—C18	2.110 (6)	C14—C15	1.526 (9)
Sn1—O2	2.130 (3)	C14—H14A	0.9700
Sn1—N1	2.169 (3)	C14—H14B	0.9700
Cl1—C4	1.745 (5)	C15—C16	1.493 (9)
N1—C7	1.287 (6)	C15—H15A	0.9700
N1—C8	1.481 (5)	C15—H15B	0.9700
O1—C1	1.308 (6)	C16—C17	1.500 (9)
O2—C9	1.271 (6)	C16—H16A	0.9700
O3—C9	1.227 (6)	C16—H16B	0.9700
C1—C2	1.406 (6)	C17—H17A	0.9600
C1—C6	1.415 (6)	C17—H17B	0.9600
C2—C3	1.362 (7)	C17—H17C	0.9600
C2—H2	0.9300	C15'—C16'	1.525 (10)
C3—C4	1.388 (7)	C15'—H15C	0.9700
C3—H3	0.9300	C15'—H15D	0.9700
C4—C5	1.355 (7)	C16'—C17'	1.518 (10)
C5—C6	1.394 (7)	C16'—H16C	0.9700
C5—H5	0.9300	C16'—H16D	0.9700
C6—C7	1.454 (6)	C17'—H17D	0.9600
C7—H7	0.9300	C17'—H17E	0.9600
C8—C9	1.538 (7)	C17'—H17F	0.9600
C8—C10	1.548 (6)	C18—C19	1.470 (9)
C8—H8	0.9800	C18—H18A	0.9700
C10—C12	1.513 (7)	C18—H18B	0.9700
C10—C11	1.523 (7)	C19—C20	1.520 (9)
C10—H10	0.9800	C19—H19A	0.9700
C11—H11A	0.9600	C19—H19B	0.9700
C11—H11B	0.9600	C20—C21	1.466 (10)
C11—H11C	0.9600	C20—H20A	0.9700
C12—C13	1.486 (9)	C20—H20B	0.9700
C12—H12A	0.9700	C21—H21A	0.9600
C12—H12B	0.9700	C21—H21B	0.9600
C13—H13A	0.9600	C21—H21C	0.9600

O1—Sn1—C14	91.5 (2)	C12—C13—H13C	109.5
O1—Sn1—C18	97.4 (2)	H13A—C13—H13C	109.5
C14—Sn1—C18	122.6 (3)	H13B—C13—H13C	109.5
O1—Sn1—O2	158.65 (13)	C15—C14—Sn1	106.6 (5)
C14—Sn1—O2	97.6 (2)	C15—C14—H14A	110.4
C18—Sn1—O2	93.9 (2)	Sn1—C14—H14A	110.4
O1—Sn1—N1	83.57 (13)	C15—C14—H14B	110.4
C14—Sn1—N1	121.7 (2)	Sn1—C14—H14B	110.4
C18—Sn1—N1	115.7 (2)	H14A—C14—H14B	108.6
O2—Sn1—N1	75.21 (13)	C16—C15—C14	115.0 (9)
C7—N1—C8	116.7 (4)	C16—C15—H15A	108.5
C7—N1—Sn1	126.7 (3)	C14—C15—H15A	108.5
C8—N1—Sn1	116.3 (3)	C16—C15—H15B	108.5
C1—O1—Sn1	132.3 (3)	C14—C15—H15B	108.5
C9—O2—Sn1	121.0 (3)	H15A—C15—H15B	107.5
O1—C1—C2	119.6 (4)	C15—C16—C17	112.4 (10)
O1—C1—C6	123.7 (4)	C15—C16—H16A	109.1
C2—C1—C6	116.7 (5)	C17—C16—H16A	109.1
C3—C2—C1	121.6 (5)	C15—C16—H16B	109.1
C3—C2—H2	119.2	C17—C16—H16B	109.1
C1—C2—H2	119.2	H16A—C16—H16B	107.9
C2—C3—C4	120.1 (5)	C16—C17—H17A	109.5
C2—C3—H3	120.0	C16—C17—H17B	109.5
C4—C3—H3	120.0	H17A—C17—H17B	109.5
C5—C4—C3	121.0 (5)	C16—C17—H17C	109.5
C5—C4—Cl1	120.7 (4)	H17A—C17—H17C	109.5
C3—C4—Cl1	118.4 (4)	H17B—C17—H17C	109.5
C4—C5—C6	119.6 (5)	C16'—C15'—H15C	110.8
C4—C5—H5	120.2	C16'—C15'—H15D	110.8
C6—C5—H5	120.2	H15C—C15'—H15D	108.9
C5—C6—C1	121.1 (4)	C17'—C16'—C15'	111.7 (13)
C5—C6—C7	116.1 (4)	C17'—C16'—H16C	109.3
C1—C6—C7	122.7 (4)	C15'—C16'—H16C	109.3
N1—C7—C6	127.7 (4)	C17'—C16'—H16D	109.3
N1—C7—H7	116.2	C15'—C16'—H16D	109.3
C6—C7—H7	116.2	H16C—C16'—H16D	107.9
N1—C8—C9	108.3 (4)	C16'—C17'—H17D	109.5
N1—C8—C10	110.1 (3)	C16'—C17'—H17E	109.5
C9—C8—C10	112.0 (4)	H17D—C17'—H17E	109.5
N1—C8—H8	108.8	C16'—C17'—H17F	109.5
C9—C8—H8	108.8	H17D—C17'—H17F	109.5
C10—C8—H8	108.8	H17E—C17'—H17F	109.5
O3—C9—O2	125.1 (5)	C19—C18—Sn1	115.5 (4)
O3—C9—C8	117.4 (5)	C19—C18—H18A	108.4
O2—C9—C8	117.4 (4)	Sn1—C18—H18A	108.4
C12—C10—C11	110.7 (4)	C19—C18—H18B	108.4
C12—C10—C8	113.3 (4)	Sn1—C18—H18B	108.4
C11—C10—C8	112.4 (4)	H18A—C18—H18B	107.5
C12—C10—H10	106.6	C18—C19—C20	112.7 (6)
C11—C10—H10	106.6	C18—C19—H19A	109.0
C8—C10—H10	106.6	C20—C19—H19A	109.0
C10—C11—H11A	109.5	C18—C19—H19B	109.0
C10—C11—H11B	109.5	C20—C19—H19B	109.0
H11A—C11—H11B	109.5	H19A—C19—H19B	107.8
C10—C11—H11C	109.5	C21—C20—C19	116.0 (7)
H11A—C11—H11C	109.5	C21—C20—H20A	108.3
H11B—C11—H11C	109.5	C19—C20—H20A	108.3
C13—C12—C10	115.4 (5)	C21—C20—H20B	108.3
C13—C12—H12A	108.4	C19—C20—H20B	108.3
C10—C12—H12A	108.4	H20A—C20—H20B	107.4
C13—C12—H12B	108.4	C20—C21—H21A	109.5
C10—C12—H12B	108.4	C20—C21—H21B	109.5
H12A—C12—H12B	107.5	H21A—C21—H21B	109.5
C12—C13—H13A	109.5	C20—C21—H21C	109.5
C12—C13—H13B	109.5	H21A—C21—H21C	109.5
H13A—C13—H13B	109.5	H21B—C21—H21C	109.5

O1—Sn1—N1—C7	−16.9 (4)	Sn1—N1—C7—C6	10.4 (7)
C14—Sn1—N1—C7	−104.7 (4)	C5—C6—C7—N1	178.8 (4)
C18—Sn1—N1—C7	78.3 (4)	C1—C6—C7—N1	3.1 (7)
O2—Sn1—N1—C7	165.4 (4)	C7—N1—C8—C9	−160.3 (4)
O1—Sn1—N1—C8	170.1 (3)	Sn1—N1—C8—C9	13.4 (4)
C14—Sn1—N1—C8	82.3 (4)	C7—N1—C8—C10	77.0 (5)
C18—Sn1—N1—C8	−94.7 (3)	Sn1—N1—C8—C10	−109.4 (4)
O2—Sn1—N1—C8	−7.5 (3)	Sn1—O2—C9—O3	−170.9 (4)
C14—Sn1—O1—C1	141.6 (5)	Sn1—O2—C9—C8	9.5 (6)
C18—Sn1—O1—C1	−95.3 (5)	N1—C8—C9—O3	165.7 (4)
O2—Sn1—O1—C1	26.2 (8)	C10—C8—C9—O3	−72.6 (6)
N1—Sn1—O1—C1	19.9 (5)	N1—C8—C9—O2	−14.7 (6)
O1—Sn1—O2—C9	−7.7 (7)	C10—C8—C9—O2	107.0 (5)
C14—Sn1—O2—C9	−122.1 (4)	N1—C8—C10—C12	−167.2 (4)
C18—Sn1—O2—C9	114.3 (4)	C9—C8—C10—C12	72.2 (5)
N1—Sn1—O2—C9	−1.2 (4)	N1—C8—C10—C11	66.3 (5)
Sn1—O1—C1—C2	167.9 (4)	C9—C8—C10—C11	−54.2 (5)
Sn1—O1—C1—C6	−14.7 (7)	C11—C10—C12—C13	−175.4 (6)
O1—C1—C2—C3	176.5 (5)	C8—C10—C12—C13	57.3 (7)
C6—C1—C2—C3	−1.0 (7)	O1—Sn1—C14—C15	144.2 (8)
C1—C2—C3—C4	0.5 (8)	C18—Sn1—C14—C15	44.4 (9)
C2—C3—C4—C5	0.8 (8)	O2—Sn1—C14—C15	−55.1 (8)
C2—C3—C4—Cl1	−180.0 (4)	N1—Sn1—C14—C15	−132.4 (8)
C3—C4—C5—C6	−1.4 (8)	Sn1—C14—C15—C16	−163.9 (11)
Cl1—C4—C5—C6	179.3 (4)	C14—C15—C16—C17	−157.9 (12)
C4—C5—C6—C1	0.9 (7)	O1—Sn1—C18—C19	79.1 (5)
C4—C5—C6—C7	−174.8 (4)	C14—Sn1—C18—C19	175.7 (4)
O1—C1—C6—C5	−177.1 (5)	O2—Sn1—C18—C19	−82.8 (5)
C2—C1—C6—C5	0.3 (7)	N1—Sn1—C18—C19	−7.3 (5)
O1—C1—C6—C7	−1.7 (7)	Sn1—C18—C19—C20	−179.5 (5)
C2—C1—C6—C7	175.7 (4)	C18—C19—C20—C21	−176.0 (6)
C8—N1—C7—C6	−176.7 (4)

Experimental details

Crystal data
Chemical formula	[Sn(C₄H₉)₂(C₁₃H₁₄ClNO₃)]
M_r	500.62
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	295
a, b, c (Å)	10.0545 (14), 14.497 (2), 15.953 (2)
V (Å³)	2325.3 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.23
Crystal size (mm)	0.35 × 0.22 × 0.08

Data collection
Diffractometer	Bruker SMART APEX area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.672, 0.908
No. of measured, independent and observed [I > 2σ(I)] reflections	18112, 4574, 3846
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.097, 1.05
No. of reflections	4574
No. of parameters	257
No. of restraints	40
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.54
Absolute structure	Flack (1983), 1978 Friedel pairs
Absolute structure parameter	0.00 (4)

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Selected bond lengths (Å) top

Sn1—O1	2.083 (3)	Sn1—O2	2.130 (3)
Sn1—C14	2.100 (6)	Sn1—N1	2.169 (3)
Sn1—C18	2.110 (6)

Acknowledgements

The authors thank the Science Foundation of Binzhou University for supporting this work (BZXYG0901 and BZXYQNLG200820).

References

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