[N-(5-Chloro-2-oxidobenzylidene)valinato-κ3O,N,O′]dicyclo­hexyl­tin(IV)

Li, J.-P.; Tian, L.-J.

doi:10.1107/S1600536807064471

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page m98

https://doi.org/10.1107/S1600536807064471

Open

access

[N-(5-Chloro-2-oxidobenzylidene)valinato-κ³O,N,O′]dicyclohexyltin(IV)

Jin-Ping Li ^a and Lai-Jin Tian ^a ^*

^aDepartment of Chemistry, Qufu Normal University, Qufu 273165, People's Republic of China
^*Correspondence e-mail: laijintian@163.com

(Received 23 November 2007; accepted 29 November 2007; online 6 December 2007)

The tin atom of the title compound, [Sn(C₆H₁₁)₂(C₁₂H₁₂ClNO₃)], adopts a distorted SnNC₂O₂ trigonal–bipyramidal geometry, and forms five- and six-membered chelate rings with the tridentate ligand.

Related literature

For related literature, see: Beltran et al. (2003 ); Dakternieks et al. (1998 ); Tian et al. (2004 , 2005 , 2006 , 2007 ).

Experimental

Crystal data

[Sn(C₆H₁₁)₂(C₁₂H₁₂ClNO₃)]
M_r = 538.66
Monoclinic, P 2₁ /n
a = 9.9830 (18) Å
b = 10.7284 (19) Å
c = 22.705 (4) Å
β = 91.759 (3)°
V = 2430.6 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.19 mm⁻¹
T = 295 (2) K
0.11 × 0.08 × 0.05 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.881, T_max = 0.943
17254 measured reflections
4754 independent reflections
3608 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.104
S = 1.04
4754 reflections
287 parameters
24 restraints
H-atom parameters constrained
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.80 e Å⁻³

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807064471/hj2007sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807064471/hj2007Isup2.hkl

checkCIF report

Comment top

The organotin complexes with Schiff bases derived from α-amino acids continue to receives attention due to their biological activities (Beltran et al., 2003; Dakternieks et al., 1998; Tian et al., 2005, 2006, 2007). The structures of two dicyclohexyltin complexes with the Schiff base ligand, [N-(5-chloro-2-oxidophenylmethylene)isoleucinato]dicyclohexyltin (Tian et al., 2004) and [N-(3,5-dibromo-2-oxidophenylmethylene)alaninato]dicyclohexyltin (Tian et al., 2007) have been reported. As a continuation of these studies, the structure of the title compound, (I), is now described.

The coordination geometry about the tin atom in (I) is that of a distorted trigonal bipyramid with two cyclohexyl groups and the imino N1 atom occupying the equatorial positions and the axial positions being occupied by phenoxide O1 atom and a unidentate carboxylate O2 atom (Fig. 1). The bond length of Sn—O1 was shorter than that of Sn—O2 and the bond angle O1—Sn—O2 was 155.75 (12) °. The monodentate mode of coordination of carboxylate is reflected in the disparate C9—O2 and C9—O3 bond lengths of 1.282 (5) and 1.221 (6) Å, respectively. The distances of bonds around the tin atom were comparable to those observed in the dicyclohexyltin complexes mentioned above.

Related literature top

For related literature, see: Beltran et al. (2003); Dakternieks et al. (1998); Tian et al. (2004, 2005, 2006, 2007).

Experimental top

The title compound was synthesized by the reaction of dicyclohexyltin dichloride (0.71 g, 2 mmol) with potassium N-(5-chlorosalicylidene)valinate (0.59 g, 2 mmol) in the presence of Et₃N (0.20 g, 2 mmol) in 40 ml me thanol. The reaction mixture was refluxed for 3 h and filtered. The yellow solid obtained, (I), by removal of solvent under reduce pressure was recrystallized from dichloromethane-petroleum ether (60–90) (1:1, V/V) and crystals of (I) were obtained from chloroform-hexane (1:1, V/V) by slow evaporation at room temperature (yield 67%, m.p. 439–440 K).

Structure description top

For related literature, see: Beltran et al. (2003); Dakternieks et al. (1998); Tian et al. (2004, 2005, 2006, 2007).

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.

Figures top

Fig. 1. The structure of (I) with displacement ellipsoids are drawn at the 30% probability level. For cyclohexyl group C19–C24, the minor disordered component has been omitted for clarity.

[N-(5-Chloro-2-oxidobenzylidene)valinato-κ³O,N,O']dicyclohexyltin(IV) top

Crystal data top

[Sn(C₆H₁₁)₂(C₁₂H₁₂ClNO₃)]	F(000) = 1104
M_r = 538.66	D_x = 1.472 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2430 reflections
a = 9.9830 (18) Å	θ = 2.6–19.8°
b = 10.7284 (19) Å	µ = 1.19 mm⁻¹
c = 22.705 (4) Å	T = 295 K
β = 91.759 (3)°	Prism, yellow
V = 2430.6 (7) Å³	0.11 × 0.08 × 0.05 mm
Z = 4

Data collection top

Bruker SMART APEX detector diffractometer	4754 independent reflections
Radiation source: fine-focus sealed tube	3608 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
φ and ω scans	θ_max = 26.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −12→12
T_min = 0.881, T_max = 0.943	k = −13→13
17254 measured reflections	l = −27→27

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0425P)² + 0.1331P] where P = (F_o² + 2F_c²)/3
4754 reflections	(Δ/σ)_max = 0.001
287 parameters	Δρ_max = 0.62 e Å⁻³
24 restraints	Δρ_min = −0.80 e Å⁻³

Crystal data top

[Sn(C₆H₁₁)₂(C₁₂H₁₂ClNO₃)]	V = 2430.6 (7) Å³
M_r = 538.66	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.9830 (18) Å	µ = 1.19 mm⁻¹
b = 10.7284 (19) Å	T = 295 K
c = 22.705 (4) Å	0.11 × 0.08 × 0.05 mm
β = 91.759 (3)°

Data collection top

Bruker SMART APEX detector diffractometer	4754 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	3608 reflections with I > 2σ(I)
T_min = 0.881, T_max = 0.943	R_int = 0.063
17254 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	24 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.04	Δρ_max = 0.62 e Å⁻³
4754 reflections	Δρ_min = −0.80 e Å⁻³
287 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	1.12598 (3)	0.20087 (3)	0.854731 (14)	0.03571 (12)
N1	1.1870 (3)	0.3911 (3)	0.83569 (15)	0.0337 (8)
O1	1.0335 (3)	0.2897 (3)	0.92506 (14)	0.0471 (8)
O2	1.2493 (3)	0.1893 (3)	0.77824 (14)	0.0482 (8)
O3	1.3868 (4)	0.2863 (3)	0.71861 (15)	0.0581 (10)
Cl1	0.75627 (17)	0.76889 (14)	0.93223 (7)	0.0752 (5)
C1	0.9725 (5)	0.3979 (4)	0.9241 (2)	0.0399 (11)
C2	0.8670 (5)	0.4189 (4)	0.9628 (2)	0.0472 (12)
H2	0.8410	0.3548	0.9875	0.057*
C3	0.8021 (5)	0.5305 (5)	0.9648 (2)	0.0512 (13)
H3	0.7324	0.5419	0.9905	0.061*
C4	0.8407 (5)	0.6271 (4)	0.9284 (2)	0.0478 (13)
C5	0.9418 (5)	0.6126 (4)	0.8906 (2)	0.0454 (12)
H5	0.9671	0.6788	0.8669	0.054*
C6	1.0087 (4)	0.4973 (4)	0.88714 (18)	0.0342 (10)
C7	1.1167 (4)	0.4896 (4)	0.84753 (19)	0.0382 (11)
H7	1.1392	0.5626	0.8281	0.046*
C8	1.3004 (4)	0.4043 (4)	0.79714 (19)	0.0386 (11)
H8	1.2814	0.4732	0.7699	0.046*
C9	1.3146 (5)	0.2848 (4)	0.7611 (2)	0.0407 (11)
C10	1.4318 (5)	0.4346 (4)	0.8325 (2)	0.0462 (12)
H10	1.5042	0.4359	0.8043	0.055*
C11	1.4686 (5)	0.3373 (5)	0.8786 (2)	0.0574 (14)
H11A	1.4726	0.2567	0.8603	0.086*
H11B	1.4022	0.3364	0.9083	0.086*
H11C	1.5545	0.3571	0.8965	0.086*
C12	1.4268 (5)	0.5636 (5)	0.8605 (2)	0.0634 (16)
H12A	1.4041	0.6243	0.8308	0.095*
H12B	1.5128	0.5833	0.8781	0.095*
H12C	1.3604	0.5645	0.8902	0.095*
C13	1.2432 (4)	0.0796 (4)	0.9097 (2)	0.0391 (11)
H13	1.3021	0.1314	0.9349	0.047*
C14	1.3322 (5)	−0.0079 (4)	0.8743 (2)	0.0499 (13)
H14A	1.2764	−0.0575	0.8476	0.060*
H14B	1.3925	0.0412	0.8510	0.060*
C15	1.4130 (6)	−0.0934 (5)	0.9149 (3)	0.0662 (16)
H15A	1.4647	−0.1505	0.8915	0.079*
H15B	1.4754	−0.0440	0.9388	0.079*
C16	1.3243 (6)	−0.1665 (5)	0.9545 (3)	0.0728 (18)
H16A	1.3794	−0.2163	0.9814	0.087*
H16B	1.2690	−0.2229	0.9308	0.087*
C17	1.2343 (6)	−0.0816 (5)	0.9898 (2)	0.0666 (16)
H17A	1.1739	−0.1319	1.0125	0.080*
H17B	1.2889	−0.0323	1.0171	0.080*
C18	1.1540 (5)	0.0037 (4)	0.9497 (2)	0.0502 (13)
H18A	1.1019	0.0600	0.9733	0.060*
H18B	1.0920	−0.0455	0.9256	0.060*
C19	0.9504 (4)	0.1411 (5)	0.8079 (2)	0.0554 (14)	0.708 (10)
H19A	0.9779	0.0674	0.7858	0.066*	0.708 (10)
C20	0.8944 (8)	0.2290 (7)	0.7624 (4)	0.055 (2)	0.708 (10)
H20A	0.9633	0.2479	0.7346	0.066*	0.708 (10)
H20B	0.8700	0.3062	0.7815	0.066*	0.708 (10)
C21	0.7723 (9)	0.1776 (11)	0.7290 (4)	0.077 (3)	0.708 (10)
H21A	0.7344	0.2422	0.7037	0.092*	0.708 (10)
H21B	0.7996	0.1091	0.7042	0.092*	0.708 (10)
C22	0.6677 (9)	0.1328 (13)	0.7698 (6)	0.081 (3)	0.708 (10)
H22A	0.5976	0.0910	0.7468	0.098*	0.708 (10)
H22B	0.6279	0.2043	0.7886	0.098*	0.708 (10)
C23	0.7204 (8)	0.0447 (10)	0.8168 (4)	0.072 (3)	0.708 (10)
H23A	0.7417	−0.0346	0.7988	0.087*	0.708 (10)
H23B	0.6509	0.0301	0.8449	0.087*	0.708 (10)
C24	0.8441 (8)	0.0943 (10)	0.8492 (4)	0.071 (3)	0.708 (10)
H24A	0.8824	0.0287	0.8739	0.085*	0.708 (10)
H24B	0.8183	0.1621	0.8748	0.085*	0.708 (10)
C19'	0.9504 (4)	0.1411 (5)	0.8079 (2)	0.0554 (14)	0.292 (10)
H19B	0.9825	0.1101	0.7702	0.066*	0.292 (10)
C20'	0.8588 (15)	0.2491 (12)	0.7912 (9)	0.055 (2)	0.292 (10)
H20C	0.8289	0.2885	0.8270	0.066*	0.292 (10)
H20D	0.9096	0.3104	0.7698	0.066*	0.292 (10)
C21'	0.737 (2)	0.212 (2)	0.7539 (10)	0.077 (3)	0.292 (10)
H21C	0.6769	0.2824	0.7495	0.092*	0.292 (10)
H21D	0.7649	0.1876	0.7150	0.092*	0.292 (10)
C22'	0.6640 (17)	0.105 (2)	0.7817 (17)	0.081 (3)	0.292 (10)
H22C	0.6241	0.1332	0.8177	0.098*	0.292 (10)
H22D	0.5921	0.0771	0.7551	0.098*	0.292 (10)
C23'	0.7553 (19)	−0.0043 (17)	0.7958 (12)	0.072 (3)	0.292 (10)
H23C	0.7850	−0.0405	0.7593	0.087*	0.292 (10)
H23D	0.7055	−0.0675	0.8164	0.087*	0.292 (10)
C24'	0.8766 (18)	0.0332 (17)	0.8333 (10)	0.071 (3)	0.292 (10)
H24C	0.8479	0.0552	0.8724	0.085*	0.292 (10)
H24D	0.9369	−0.0374	0.8372	0.085*	0.292 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0373 (2)	0.02864 (17)	0.04125 (19)	0.00125 (14)	0.00194 (13)	−0.00021 (15)
N1	0.035 (2)	0.033 (2)	0.034 (2)	0.0053 (16)	0.0086 (16)	0.0009 (16)
O1	0.056 (2)	0.0334 (18)	0.053 (2)	0.0095 (15)	0.0164 (17)	0.0055 (15)
O2	0.063 (2)	0.0366 (19)	0.046 (2)	−0.0013 (16)	0.0115 (17)	−0.0090 (15)
O3	0.071 (3)	0.057 (2)	0.048 (2)	0.0110 (19)	0.0197 (19)	−0.0038 (18)
Cl1	0.0850 (11)	0.0588 (9)	0.0823 (11)	0.0411 (8)	0.0093 (9)	−0.0086 (8)
C1	0.043 (3)	0.034 (3)	0.043 (3)	0.002 (2)	−0.001 (2)	−0.003 (2)
C2	0.048 (3)	0.041 (3)	0.053 (3)	−0.003 (2)	0.018 (2)	−0.001 (2)
C3	0.045 (3)	0.055 (3)	0.055 (3)	0.005 (2)	0.012 (2)	−0.015 (3)
C4	0.048 (3)	0.042 (3)	0.052 (3)	0.016 (2)	−0.006 (3)	−0.007 (2)
C5	0.052 (3)	0.039 (3)	0.045 (3)	0.007 (2)	−0.002 (2)	−0.002 (2)
C6	0.038 (3)	0.031 (2)	0.034 (2)	0.0065 (19)	0.004 (2)	−0.0007 (19)
C7	0.043 (3)	0.029 (2)	0.042 (3)	0.000 (2)	0.001 (2)	0.002 (2)
C8	0.043 (3)	0.034 (2)	0.039 (3)	−0.001 (2)	0.009 (2)	0.005 (2)
C9	0.047 (3)	0.040 (3)	0.035 (3)	0.012 (2)	−0.001 (2)	−0.002 (2)
C10	0.041 (3)	0.044 (3)	0.054 (3)	−0.007 (2)	0.011 (2)	−0.005 (2)
C11	0.052 (3)	0.056 (3)	0.063 (4)	−0.002 (3)	−0.007 (3)	0.002 (3)
C12	0.067 (4)	0.050 (3)	0.073 (4)	−0.012 (3)	0.003 (3)	−0.009 (3)
C13	0.043 (3)	0.027 (2)	0.047 (3)	0.001 (2)	−0.001 (2)	0.001 (2)
C14	0.047 (3)	0.051 (3)	0.052 (3)	0.010 (2)	0.012 (2)	0.005 (2)
C15	0.059 (4)	0.059 (4)	0.082 (4)	0.026 (3)	0.015 (3)	0.008 (3)
C16	0.087 (5)	0.052 (3)	0.079 (4)	0.027 (3)	0.009 (4)	0.018 (3)
C17	0.085 (4)	0.054 (3)	0.062 (4)	0.016 (3)	0.014 (3)	0.014 (3)
C18	0.054 (3)	0.039 (3)	0.058 (3)	0.008 (2)	0.016 (3)	0.009 (2)
C19	0.040 (3)	0.063 (3)	0.063 (4)	−0.007 (3)	−0.006 (3)	−0.006 (3)
C20	0.059 (5)	0.072 (5)	0.033 (5)	−0.011 (4)	−0.009 (4)	0.005 (4)
C21	0.075 (6)	0.097 (8)	0.055 (7)	−0.017 (5)	−0.026 (5)	0.011 (5)
C22	0.049 (4)	0.109 (8)	0.086 (8)	−0.004 (4)	−0.016 (4)	0.002 (6)
C23	0.050 (5)	0.081 (8)	0.085 (8)	−0.019 (5)	−0.004 (5)	0.006 (5)
C24	0.050 (5)	0.086 (8)	0.076 (6)	−0.020 (5)	−0.015 (4)	0.028 (6)
C19'	0.040 (3)	0.063 (3)	0.063 (4)	−0.007 (3)	−0.006 (3)	−0.006 (3)
C20'	0.059 (5)	0.072 (5)	0.033 (5)	−0.011 (4)	−0.009 (4)	0.005 (4)
C21'	0.075 (6)	0.097 (8)	0.055 (7)	−0.017 (5)	−0.026 (5)	0.011 (5)
C22'	0.049 (4)	0.109 (8)	0.086 (8)	−0.004 (4)	−0.016 (4)	0.002 (6)
C23'	0.050 (5)	0.081 (8)	0.085 (8)	−0.019 (5)	−0.004 (5)	0.006 (5)
C24'	0.050 (5)	0.086 (8)	0.076 (6)	−0.020 (5)	−0.015 (4)	0.028 (6)

Geometric parameters (Å, º) top

Sn1—O1	2.098 (3)	C15—H15A	0.9700
Sn1—C19	2.122 (4)	C15—H15B	0.9700
Sn1—C13	2.128 (4)	C16—C17	1.525 (7)
Sn1—O2	2.163 (3)	C16—H16A	0.9700
Sn1—N1	2.177 (4)	C16—H16B	0.9700
N1—C7	1.301 (5)	C17—C18	1.504 (6)
N1—C8	1.459 (5)	C17—H17A	0.9700
O1—C1	1.311 (5)	C17—H17B	0.9700
O2—C9	1.282 (5)	C18—H18A	0.9700
O3—C9	1.221 (6)	C18—H18B	0.9700
Cl1—C4	1.742 (5)	C19—C20	1.494 (7)
C1—C2	1.409 (6)	C19—C24	1.524 (7)
C1—C6	1.411 (6)	C19—H19A	0.9800
C2—C3	1.363 (6)	C20—C21	1.519 (7)
C2—H2	0.9300	C20—H20A	0.9700
C3—C4	1.387 (7)	C20—H20B	0.9700
C3—H3	0.9300	C21—C22	1.496 (8)
C4—C5	1.354 (6)	C21—H21A	0.9700
C5—C6	1.410 (6)	C21—H21B	0.9700
C5—H5	0.9300	C22—C23	1.509 (8)
C6—C7	1.428 (6)	C22—H22A	0.9700
C7—H7	0.9300	C22—H22B	0.9700
C8—C9	1.530 (6)	C23—C24	1.515 (7)
C8—C10	1.552 (6)	C23—H23A	0.9700
C8—H8	0.9800	C23—H23B	0.9700
C10—C11	1.516 (7)	C24—H24A	0.9700
C10—C12	1.525 (6)	C24—H24B	0.9700
C10—H10	0.9800	C20'—C21'	1.515 (9)
C11—H11A	0.9600	C20'—H20C	0.9700
C11—H11B	0.9600	C20'—H20D	0.9700
C11—H11C	0.9600	C21'—C22'	1.510 (10)
C12—H12A	0.9600	C21'—H21C	0.9700
C12—H12B	0.9600	C21'—H21D	0.9700
C12—H12C	0.9600	C22'—C23'	1.510 (10)
C13—C18	1.527 (6)	C22'—H22C	0.9700
C13—C14	1.535 (6)	C22'—H22D	0.9700
C13—H13	0.9800	C23'—C24'	1.513 (10)
C14—C15	1.516 (6)	C23'—H23C	0.9700
C14—H14A	0.9700	C23'—H23D	0.9700
C14—H14B	0.9700	C24'—H24C	0.9700
C15—C16	1.502 (7)	C24'—H24D	0.9700

O1—Sn1—C19	98.23 (17)	H15A—C15—H15B	108.0
O1—Sn1—C13	94.51 (15)	C15—C16—C17	111.7 (5)
C19—Sn1—C13	122.71 (18)	C15—C16—H16A	109.3
O1—Sn1—O2	155.75 (12)	C17—C16—H16A	109.3
C19—Sn1—O2	93.54 (17)	C15—C16—H16B	109.3
C13—Sn1—O2	96.83 (15)	C17—C16—H16B	109.3
O1—Sn1—N1	81.80 (12)	H16A—C16—H16B	107.9
C19—Sn1—N1	114.56 (16)	C18—C17—C16	110.9 (5)
C13—Sn1—N1	122.50 (15)	C18—C17—H17A	109.5
O2—Sn1—N1	74.02 (12)	C16—C17—H17A	109.5
C7—N1—C8	118.6 (4)	C18—C17—H17B	109.5
C7—N1—Sn1	124.3 (3)	C16—C17—H17B	109.5
C8—N1—Sn1	115.9 (3)	H17A—C17—H17B	108.1
C1—O1—Sn1	127.2 (3)	C17—C18—C13	112.0 (4)
C9—O2—Sn1	120.4 (3)	C17—C18—H18A	109.2
O1—C1—C2	119.1 (4)	C13—C18—H18A	109.2
O1—C1—C6	123.4 (4)	C17—C18—H18B	109.2
C2—C1—C6	117.4 (4)	C13—C18—H18B	109.2
C3—C2—C1	121.8 (5)	H18A—C18—H18B	107.9
C3—C2—H2	119.1	C20—C19—C24	112.4 (5)
C1—C2—H2	119.1	C20—C19—Sn1	116.2 (4)
C2—C3—C4	119.7 (5)	C24—C19—Sn1	111.7 (4)
C2—C3—H3	120.2	C20—C19—H19A	105.1
C4—C3—H3	120.2	C24—C19—H19A	105.1
C5—C4—C3	121.2 (4)	Sn1—C19—H19A	105.1
C5—C4—Cl1	120.2 (4)	C19—C20—C21	113.2 (6)
C3—C4—Cl1	118.6 (4)	C19—C20—H20A	108.9
C4—C5—C6	120.0 (5)	C21—C20—H20A	108.9
C4—C5—H5	120.0	C19—C20—H20B	108.9
C6—C5—H5	120.0	C21—C20—H20B	108.9
C5—C6—C1	120.0 (4)	H20A—C20—H20B	107.8
C5—C6—C7	117.0 (4)	C22—C21—C20	111.8 (7)
C1—C6—C7	122.9 (4)	C22—C21—H21A	109.2
N1—C7—C6	126.9 (4)	C20—C21—H21A	109.2
N1—C7—H7	116.6	C22—C21—H21B	109.2
C6—C7—H7	116.6	C20—C21—H21B	109.2
N1—C8—C9	109.1 (4)	H21A—C21—H21B	107.9
N1—C8—C10	111.7 (4)	C21—C22—C23	113.9 (7)
C9—C8—C10	111.2 (4)	C21—C22—H22A	108.8
N1—C8—H8	108.3	C23—C22—H22A	108.8
C9—C8—H8	108.3	C21—C22—H22B	108.8
C10—C8—H8	108.3	C23—C22—H22B	108.8
O3—C9—O2	124.6 (4)	H22A—C22—H22B	107.7
O3—C9—C8	118.6 (4)	C22—C23—C24	112.7 (7)
O2—C9—C8	116.8 (4)	C22—C23—H23A	109.1
C11—C10—C12	110.4 (4)	C24—C23—H23A	109.1
C11—C10—C8	113.4 (4)	C22—C23—H23B	109.1
C12—C10—C8	111.6 (4)	C24—C23—H23B	109.1
C11—C10—H10	107.1	H23A—C23—H23B	107.8
C12—C10—H10	107.1	C23—C24—C19	112.9 (6)
C8—C10—H10	107.1	C23—C24—H24A	109.0
C10—C11—H11A	109.5	C19—C24—H24A	109.0
C10—C11—H11B	109.5	C23—C24—H24B	109.0
H11A—C11—H11B	109.5	C19—C24—H24B	109.0
C10—C11—H11C	109.5	H24A—C24—H24B	107.8
H11A—C11—H11C	109.5	C21'—C20'—H20C	108.8
H11B—C11—H11C	109.5	C21'—C20'—H20D	108.8
C10—C12—H12A	109.5	H20C—C20'—H20D	107.7
C10—C12—H12B	109.5	C22'—C21'—C20'	110.9 (12)
H12A—C12—H12B	109.5	C22'—C21'—H21C	109.5
C10—C12—H12C	109.5	C20'—C21'—H21C	109.5
H12A—C12—H12C	109.5	C22'—C21'—H21D	109.5
H12B—C12—H12C	109.5	C20'—C21'—H21D	109.5
C18—C13—C14	110.0 (4)	H21C—C21'—H21D	108.0
C18—C13—Sn1	110.8 (3)	C23'—C22'—C21'	112.4 (14)
C14—C13—Sn1	112.6 (3)	C23'—C22'—H22C	109.1
C18—C13—H13	107.8	C21'—C22'—H22C	109.1
C14—C13—H13	107.8	C23'—C22'—H22D	109.1
Sn1—C13—H13	107.8	C21'—C22'—H22D	109.1
C15—C14—C13	111.0 (4)	H22C—C22'—H22D	107.9
C15—C14—H14A	109.4	C22'—C23'—C24'	112.4 (13)
C13—C14—H14A	109.4	C22'—C23'—H23C	109.1
C15—C14—H14B	109.4	C24'—C23'—H23C	109.1
C13—C14—H14B	109.4	C22'—C23'—H23D	109.1
H14A—C14—H14B	108.0	C24'—C23'—H23D	109.1
C16—C15—C14	111.5 (4)	H23C—C23'—H23D	107.8
C16—C15—H15A	109.3	C23'—C24'—H24C	109.1
C14—C15—H15A	109.3	C23'—C24'—H24D	109.1
C16—C15—H15B	109.3	H24C—C24'—H24D	107.8
C14—C15—H15B	109.3

O1—Sn1—N1—C7	−31.2 (3)	C10—C8—C9—O3	−70.2 (5)
C19—Sn1—N1—C7	64.1 (4)	N1—C8—C9—O2	−14.2 (5)
C13—Sn1—N1—C7	−121.4 (3)	C10—C8—C9—O2	109.4 (5)
O2—Sn1—N1—C7	150.7 (4)	N1—C8—C10—C11	58.1 (5)
O1—Sn1—N1—C8	161.1 (3)	C9—C8—C10—C11	−64.0 (5)
C19—Sn1—N1—C8	−103.5 (3)	N1—C8—C10—C12	−67.3 (5)
C13—Sn1—N1—C8	71.0 (3)	C9—C8—C10—C12	170.6 (4)
O2—Sn1—N1—C8	−17.0 (3)	O1—Sn1—C13—C18	56.4 (3)
C19—Sn1—O1—C1	−75.0 (4)	C19—Sn1—C13—C18	−46.4 (4)
C13—Sn1—O1—C1	161.0 (4)	O2—Sn1—C13—C18	−145.1 (3)
O2—Sn1—O1—C1	43.2 (6)	N1—Sn1—C13—C18	139.5 (3)
N1—Sn1—O1—C1	38.8 (4)	O1—Sn1—C13—C14	180.0 (3)
O1—Sn1—O2—C9	4.6 (5)	C19—Sn1—C13—C14	77.2 (4)
C19—Sn1—O2—C9	123.7 (4)	O2—Sn1—C13—C14	−21.5 (3)
C13—Sn1—O2—C9	−112.7 (3)	N1—Sn1—C13—C14	−96.9 (3)
N1—Sn1—O2—C9	9.2 (3)	C18—C13—C14—C15	−55.4 (5)
Sn1—O1—C1—C2	150.7 (3)	Sn1—C13—C14—C15	−179.5 (4)
Sn1—O1—C1—C6	−30.9 (6)	C13—C14—C15—C16	56.0 (6)
O1—C1—C2—C3	178.3 (4)	C14—C15—C16—C17	−55.6 (7)
C6—C1—C2—C3	−0.2 (7)	C15—C16—C17—C18	54.9 (7)
C1—C2—C3—C4	−0.5 (8)	C16—C17—C18—C13	−55.4 (6)
C2—C3—C4—C5	0.1 (8)	C14—C13—C18—C17	55.8 (6)
C2—C3—C4—Cl1	−179.8 (4)	Sn1—C13—C18—C17	−179.1 (4)
C3—C4—C5—C6	0.8 (7)	O1—Sn1—C19—C20	90.7 (5)
Cl1—C4—C5—C6	−179.2 (4)	C13—Sn1—C19—C20	−168.5 (5)
C4—C5—C6—C1	−1.5 (7)	O2—Sn1—C19—C20	−68.0 (5)
C4—C5—C6—C7	−178.3 (4)	N1—Sn1—C19—C20	6.0 (6)
O1—C1—C6—C5	−177.2 (4)	O1—Sn1—C19—C24	−40.1 (6)
C2—C1—C6—C5	1.2 (6)	C13—Sn1—C19—C24	60.7 (6)
O1—C1—C6—C7	−0.6 (7)	O2—Sn1—C19—C24	161.2 (6)
C2—C1—C6—C7	177.8 (4)	N1—Sn1—C19—C24	−124.8 (6)
C8—N1—C7—C6	−175.4 (4)	C24—C19—C20—C21	−51.9 (9)
Sn1—N1—C7—C6	17.3 (6)	Sn1—C19—C20—C21	177.6 (5)
C5—C6—C7—N1	−176.5 (4)	C19—C20—C21—C22	52.2 (11)
C1—C6—C7—N1	6.8 (7)	C20—C21—C22—C23	−51.0 (14)
C7—N1—C8—C9	−146.8 (4)	C21—C22—C23—C24	50.0 (14)
Sn1—N1—C8—C9	21.6 (4)	C22—C23—C24—C19	−48.9 (11)
C7—N1—C8—C10	89.9 (5)	C20—C19—C24—C23	50.3 (9)
Sn1—N1—C8—C10	−101.7 (3)	Sn1—C19—C24—C23	−177.0 (6)
Sn1—O2—C9—O3	179.7 (4)	C20'—C21'—C22'—C23'	−53 (3)
Sn1—O2—C9—C8	0.1 (5)	C21'—C22'—C23'—C24'	54 (3)
N1—C8—C9—O3	166.2 (4)

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₁₁)₂(C₁₂H₁₂ClNO₃)]
M_r	538.66
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	9.9830 (18), 10.7284 (19), 22.705 (4)
β (°)	91.759 (3)
V (Å³)	2430.6 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.19
Crystal size (mm)	0.11 × 0.08 × 0.05

Data collection
Diffractometer	Bruker SMART APEX detector
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.881, 0.943
No. of measured, independent and observed [I > 2σ(I)] reflections	17254, 4754, 3608
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.104, 1.04
No. of reflections	4754
No. of parameters	287
No. of restraints	24
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.80

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

Acknowledgements

The authors thank the Science Foundation of Shandong Province and Qufu Normal University for supporting this work.

References

Beltran, H. I., Zamudio-Rivera, L. S., Mancilla, T., Santillan, R. & Farfan, N. (2003). Chem. Eur. J. 9, 2291–2306. Web of Science CSD CrossRef PubMed CAS Google Scholar
Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dakternieks, D., Basu Baul, T. S., Dutta, S. & Tiekink, E. R. T. (1998). Organometallics, 17, 3058–3062. Web of Science CSD CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Tian, L., Liu, X., Shang, Z., Li, D. & Yu, Q. (2004). Appl. Organomet. Chem. 18, 483–484. Web of Science CSD CrossRef CAS Google Scholar
Tian, L., Qian, B., Sun, Y., Zheng, X., Yang, M., Li, H. & Liu, X. (2005). Appl. Organomet. Chem. 19, 980–987. Web of Science CSD CrossRef CAS Google Scholar
Tian, L., Shang, Z., Zheng, X., Sun, Y., You, Y., Qian, B. & Liu, X. (2006). Appl. Organomet. Chem. 19, 74–80. Web of Science CSD CrossRef Google Scholar
Tian, L., Sun, Y., Zheng, X., Liu, X., You, Y., Liu, X. & Qian, B. (2007). Chin. J. Chem. 25, 312–318. Web of Science CSD CrossRef CAS Google Scholar