Dimethyl­bis­(2-methyl­quinolin-8-olato-κ2N,O)tin(IV)

Najafi, E.; Amini, M.M.; Ng, S.W.

doi:10.1107/S1600536812047393

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page m1551

doi:10.1107/S1600536812047393

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Dimethylbis(2-methylquinolin-8-olato-κ²N,O)tin(IV)

Ezzatollah Najafi,^a Mostafa M. Amini ^a and Seik Weng Ng ^b,^c ^*

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 17 November 2012; accepted 19 November 2012; online 28 November 2012)

The Sn^IV cation in the title compound, [Sn(CH₃)₂(C₁₀H₈NO)₂], is N,O-chelated by two 2-methylquinolin-8-olate anions and coordinated by two methyl groups in a skew-trapezoidal bipyramidal geometry. In the molecule, the two quinoline ring systems are twisted to one another at 10.91 (18)°. The dimethyltin skeleton [C—Sn—C = 149.6 (2)°] is bent over the longer edge of the trapezoid that is defined by the four chelating atoms. Weak intermolecular C—H⋯O hydrogen bonding occurs in the crystal.

Related literature

For ethylpropylbis(2-methyl-8-quinolinato)tin(IV), see: Das et al. (1984 ).

Experimental

Crystal data

[Sn(CH₃)₂(C₁₀H₈NO)₂]
M_r = 465.11
Monoclinic, P 2₁ /n
a = 8.0434 (4) Å
b = 20.6952 (10) Å
c = 12.0102 (6) Å
β = 95.420 (5)°
V = 1990.28 (17) Å³
Z = 4
Mo Kα radiation
μ = 1.30 mm⁻¹
T = 295 K
0.25 × 0.25 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.737, T_max = 0.938
20963 measured reflections
4600 independent reflections
3410 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.094
S = 1.05
4600 reflections
246 parameters
30 restraints
H-atom parameters constrained
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3C⋯O2ⁱ	0.96	2.49	3.353 (7)	149
Symmetry code: (i) x-1, y, z.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812047393/xu5653sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812047393/xu5653Isup2.hkl

checkCIF report

Comment top

The deprotonated 2-methy-8-hydroxyquinoline ligand chelates to the metal atom of a diorganotin skeleton bu the proximity of the methyl substitutent in the aromatic system results in a six-coordinate geometry that is distorted towards a skew-trapezoidal bipyramid, as noted in the ethylpropyltin derivative (Kumar Das et al., 1984). The Sn^IV atom in the dimethyltin analog (Scheme I, Fig. 1) is chelated by the 2-methyl-8-quinolinate ion and it exists in a skew-trapezoidal bipyramidal geometry [C–Sn–C 149.6 (2) °].

The dimethyltin skeleton is arched over the long side of the trazepoid defined by the chelating N and O atoms.

Related literature top

For ethylpropylbis(2-methyl-8-quinolinato)tin(IV), see: Kumar Das et al. (1984).

Experimental top

Dimethyltin dichloride (0.22 g, 1 mmol) and 2-methyl-8-hydroxyquinoline (0.36 g, 2 mmol) were loaded into a convection tube; the tube was filled with ethyl alcohol and kept at 333 K. Yellow crystals were collected from the side arm after several days.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of (CH₃)₂Sn(C₁₀H₈NO)₂ at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Dimethylbis(2-methylquinolin-8-olato-κ²N,O)tin(IV) top

Crystal data top

[Sn(CH₃)₂(C₁₀H₈NO)₂]	F(000) = 936
M_r = 465.11	D_x = 1.552 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4858 reflections
a = 8.0434 (4) Å	θ = 2.9–27.5°
b = 20.6952 (10) Å	µ = 1.30 mm⁻¹
c = 12.0102 (6) Å	T = 295 K
β = 95.420 (5)°	Prism, yellow
V = 1990.28 (17) Å³	0.25 × 0.25 × 0.05 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4600 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3410 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.046
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.9°
ω scan	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −26→26
T_min = 0.737, T_max = 0.938	l = −11→15
20963 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0354P)² + 1.6968P] where P = (F_o² + 2F_c²)/3
4600 reflections	(Δ/σ)_max = 0.001
246 parameters	Δρ_max = 0.79 e Å⁻³
30 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

[Sn(CH₃)₂(C₁₀H₈NO)₂]	V = 1990.28 (17) Å³
M_r = 465.11	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.0434 (4) Å	µ = 1.30 mm⁻¹
b = 20.6952 (10) Å	T = 295 K
c = 12.0102 (6) Å	0.25 × 0.25 × 0.05 mm
β = 95.420 (5)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4600 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	3410 reflections with I > 2σ(I)
T_min = 0.737, T_max = 0.938	R_int = 0.046
20963 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	30 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.05	Δρ_max = 0.79 e Å⁻³
4600 reflections	Δρ_min = −0.49 e Å⁻³
246 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.31642 (3)	0.682497 (12)	0.39615 (2)	0.04048 (10)
O1	0.4151 (3)	0.60834 (13)	0.3067 (3)	0.0537 (7)
O2	0.5350 (3)	0.72786 (13)	0.3645 (2)	0.0511 (7)
N1	0.1010 (4)	0.59118 (17)	0.3762 (3)	0.0524 (9)
N2	0.3308 (6)	0.79119 (19)	0.4985 (3)	0.0644 (11)
C1	0.1501 (6)	0.7308 (2)	0.2773 (4)	0.0610 (12)
H1A	0.1756	0.7195	0.2033	0.091*
H1B	0.1618	0.7767	0.2876	0.091*
H1C	0.0376	0.7183	0.2871	0.091*
C3	−0.1319 (7)	0.6398 (3)	0.4603 (6)	0.099 (2)
H3A	−0.0620	0.6773	0.4589	0.149*
H3B	−0.1453	0.6285	0.5365	0.149*
H3C	−0.2392	0.6489	0.4216	0.149*
C2	0.3722 (6)	0.6462 (2)	0.5594 (4)	0.0641 (13)
H2A	0.3911	0.6005	0.5561	0.096*
H2B	0.2802	0.6546	0.6028	0.096*
H2C	0.4707	0.6671	0.5937	0.096*
C4	−0.0528 (6)	0.5848 (3)	0.4043 (4)	0.0696 (15)
C5	−0.1415 (7)	0.5271 (4)	0.3834 (5)	0.085 (2)
H5	−0.2499	0.5234	0.4037	0.102*
C6	−0.0701 (9)	0.4767 (3)	0.3338 (5)	0.093 (2)
H6	−0.1293	0.4384	0.3215	0.112*
C7	0.0916 (7)	0.4816 (2)	0.3008 (4)	0.0701 (16)
C8	0.1728 (11)	0.4328 (3)	0.2467 (5)	0.095 (2)
H8	0.1207	0.3931	0.2323	0.114*
C9	0.3267 (11)	0.4433 (3)	0.2156 (5)	0.098 (2)
H9	0.3788	0.4105	0.1790	0.117*
C10	0.4118 (7)	0.5019 (2)	0.2362 (4)	0.0684 (14)
H10	0.5186	0.5072	0.2140	0.082*
C11	0.3376 (6)	0.5519 (2)	0.2895 (4)	0.0511 (10)
C12	0.1746 (5)	0.5415 (2)	0.3235 (4)	0.0510 (11)
C13	0.0724 (11)	0.7858 (4)	0.5910 (6)	0.134 (3)
H13A	0.0170	0.8107	0.6438	0.201*
H13B	0.0992	0.7438	0.6218	0.201*
H13C	0.0002	0.7811	0.5231	0.201*
C14	0.2287 (10)	0.8192 (3)	0.5665 (4)	0.096 (2)
C15	0.2632 (14)	0.8788 (4)	0.6124 (6)	0.125 (3)
H15	0.1897	0.8978	0.6580	0.150*
C16	0.3987 (12)	0.9086 (3)	0.5919 (6)	0.106 (3)
H16	0.4212	0.9485	0.6255	0.127*
C17	0.5152 (11)	0.8834 (3)	0.5205 (6)	0.100 (2)
C18	0.6547 (14)	0.9089 (4)	0.4912 (8)	0.132 (3)
H18	0.6857	0.9488	0.5225	0.159*
C19	0.7582 (10)	0.8829 (4)	0.4195 (8)	0.117 (3)
H19	0.8523	0.9053	0.4014	0.140*
C20	0.7173 (7)	0.8171 (3)	0.3703 (6)	0.095 (2)
H20	0.7846	0.7974	0.3213	0.114*
C21	0.5752 (6)	0.7875 (2)	0.4016 (4)	0.0576 (13)
C22	0.4726 (8)	0.8203 (2)	0.4745 (4)	0.0658 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.03944 (16)	0.03883 (16)	0.04375 (17)	0.00020 (12)	0.00699 (11)	0.00239 (12)
O1	0.0472 (16)	0.0403 (16)	0.076 (2)	−0.0065 (13)	0.0160 (15)	−0.0110 (14)
O2	0.0461 (16)	0.0464 (17)	0.0624 (18)	−0.0095 (13)	0.0135 (14)	−0.0011 (14)
N1	0.0410 (19)	0.052 (2)	0.063 (2)	−0.0057 (16)	−0.0012 (17)	0.0181 (18)
N2	0.099 (3)	0.053 (2)	0.039 (2)	0.023 (2)	−0.006 (2)	−0.0055 (18)
C1	0.060 (3)	0.058 (3)	0.062 (3)	0.004 (2)	−0.005 (2)	0.009 (2)
C3	0.055 (3)	0.110 (5)	0.138 (6)	0.022 (3)	0.034 (4)	0.050 (5)
C2	0.067 (3)	0.068 (3)	0.056 (3)	−0.004 (2)	0.002 (2)	0.020 (2)
C4	0.041 (2)	0.089 (4)	0.078 (3)	−0.010 (3)	−0.004 (2)	0.037 (3)
C5	0.053 (3)	0.118 (5)	0.079 (4)	−0.036 (3)	−0.013 (3)	0.047 (4)
C6	0.097 (5)	0.103 (5)	0.071 (4)	−0.065 (4)	−0.029 (4)	0.038 (4)
C7	0.093 (4)	0.058 (3)	0.053 (3)	−0.034 (3)	−0.021 (3)	0.014 (2)
C8	0.159 (7)	0.053 (3)	0.068 (4)	−0.040 (4)	−0.013 (4)	−0.005 (3)
C9	0.162 (7)	0.050 (3)	0.078 (4)	−0.007 (4)	−0.001 (4)	−0.018 (3)
C10	0.088 (4)	0.047 (3)	0.069 (3)	0.002 (3)	0.004 (3)	−0.010 (2)
C11	0.062 (3)	0.038 (2)	0.052 (2)	−0.001 (2)	−0.002 (2)	−0.0003 (19)
C12	0.055 (3)	0.046 (2)	0.049 (2)	−0.010 (2)	−0.010 (2)	0.011 (2)
C13	0.144 (7)	0.190 (8)	0.077 (4)	0.086 (7)	0.060 (5)	0.019 (5)
C14	0.160 (7)	0.085 (4)	0.040 (3)	0.066 (4)	−0.009 (4)	−0.014 (3)
C15	0.174 (7)	0.116 (6)	0.080 (4)	0.063 (5)	−0.015 (5)	−0.021 (4)
C16	0.172 (6)	0.062 (4)	0.072 (4)	0.042 (4)	−0.045 (4)	−0.032 (3)
C17	0.132 (5)	0.067 (4)	0.089 (4)	0.000 (4)	−0.054 (4)	0.010 (3)
C18	0.149 (7)	0.094 (5)	0.139 (6)	−0.020 (5)	−0.067 (6)	0.026 (5)
C19	0.086 (4)	0.097 (5)	0.156 (6)	−0.053 (4)	−0.045 (4)	0.062 (4)
C20	0.057 (3)	0.077 (4)	0.143 (6)	−0.022 (3)	−0.025 (4)	0.053 (4)
C21	0.054 (3)	0.049 (3)	0.065 (3)	−0.013 (2)	−0.018 (2)	0.023 (2)
C22	0.100 (4)	0.037 (2)	0.053 (3)	0.007 (3)	−0.033 (3)	−0.004 (2)

Geometric parameters (Å, º) top

Sn1—O2	2.060 (3)	C7—C8	1.397 (9)
Sn1—O1	2.073 (3)	C7—C12	1.422 (6)
Sn1—C2	2.108 (4)	C8—C9	1.344 (10)
Sn1—C1	2.113 (4)	C8—H8	0.9300
Sn1—N1	2.560 (3)	C9—C10	1.403 (8)
Sn1—N2	2.561 (4)	C9—H9	0.9300
O1—C11	1.331 (5)	C10—C11	1.381 (6)
O2—C21	1.341 (5)	C10—H10	0.9300
N1—C4	1.320 (6)	C11—C12	1.426 (6)
N1—C12	1.369 (6)	C13—C14	1.489 (11)
N2—C14	1.343 (7)	C13—H13A	0.9600
N2—C22	1.345 (7)	C13—H13B	0.9600
C1—H1A	0.9600	C13—H13C	0.9600
C1—H1B	0.9600	C14—C15	1.368 (10)
C1—H1C	0.9600	C15—C16	1.296 (11)
C3—C4	1.495 (8)	C15—H15	0.9300
C3—H3A	0.9600	C16—C17	1.427 (11)
C3—H3B	0.9600	C16—H16	0.9300
C3—H3C	0.9600	C17—C18	1.318 (12)
C2—H2A	0.9600	C17—C22	1.448 (7)
C2—H2B	0.9600	C18—C19	1.364 (12)
C2—H2C	0.9600	C18—H18	0.9300
C4—C5	1.400 (8)	C19—C20	1.508 (10)
C5—C6	1.356 (9)	C19—H19	0.9300
C5—H5	0.9300	C20—C21	1.380 (7)
C6—C7	1.399 (9)	C20—H20	0.9300
C6—H6	0.9300	C21—C22	1.430 (8)

O2—Sn1—O1	82.34 (11)	C8—C7—C12	119.3 (5)
O2—Sn1—C2	102.92 (16)	C6—C7—C12	116.1 (6)
O1—Sn1—C2	99.20 (17)	C9—C8—C7	119.6 (5)
O2—Sn1—C1	99.00 (16)	C9—C8—H8	120.2
O1—Sn1—C1	104.44 (16)	C7—C8—H8	120.2
C2—Sn1—C1	149.6 (2)	C8—C9—C10	122.6 (6)
O2—Sn1—N1	154.31 (12)	C8—C9—H9	118.7
O1—Sn1—N1	72.16 (12)	C10—C9—H9	118.7
C2—Sn1—N1	84.66 (15)	C11—C10—C9	120.3 (6)
C1—Sn1—N1	84.63 (15)	C11—C10—H10	119.9
O2—Sn1—N2	71.80 (14)	C9—C10—H10	119.9
O1—Sn1—N2	153.73 (14)	O1—C11—C10	120.8 (4)
C2—Sn1—N2	82.55 (16)	O1—C11—C12	121.2 (4)
C1—Sn1—N2	84.58 (15)	C10—C11—C12	118.0 (4)
N1—Sn1—N2	133.87 (15)	N1—C12—C7	121.8 (5)
C11—O1—Sn1	122.2 (3)	N1—C12—C11	117.9 (4)
C21—O2—Sn1	122.8 (3)	C7—C12—C11	120.2 (5)
C4—N1—C12	120.0 (4)	C14—C13—H13A	109.5
C4—N1—Sn1	133.9 (4)	C14—C13—H13B	109.5
C12—N1—Sn1	106.2 (3)	H13A—C13—H13B	109.5
C14—N2—C22	121.1 (5)	C14—C13—H13C	109.5
C14—N2—Sn1	132.0 (5)	H13A—C13—H13C	109.5
C22—N2—Sn1	106.9 (3)	H13B—C13—H13C	109.5
Sn1—C1—H1A	109.5	N2—C14—C15	121.4 (9)
Sn1—C1—H1B	109.5	N2—C14—C13	119.7 (6)
H1A—C1—H1B	109.5	C15—C14—C13	118.8 (7)
Sn1—C1—H1C	109.5	C16—C15—C14	119.6 (9)
H1A—C1—H1C	109.5	C16—C15—H15	120.2
H1B—C1—H1C	109.5	C14—C15—H15	120.2
C4—C3—H3A	109.5	C15—C16—C17	123.5 (7)
C4—C3—H3B	109.5	C15—C16—H16	118.2
H3A—C3—H3B	109.5	C17—C16—H16	118.2
C4—C3—H3C	109.5	C18—C17—C16	129.7 (8)
H3A—C3—H3C	109.5	C18—C17—C22	115.9 (9)
H3B—C3—H3C	109.5	C16—C17—C22	114.5 (7)
Sn1—C2—H2A	109.5	C17—C18—C19	126.6 (9)
Sn1—C2—H2B	109.5	C17—C18—H18	116.7
H2A—C2—H2B	109.5	C19—C18—H18	116.7
Sn1—C2—H2C	109.5	C18—C19—C20	118.7 (7)
H2A—C2—H2C	109.5	C18—C19—H19	120.6
H2B—C2—H2C	109.5	C20—C19—H19	120.6
N1—C4—C5	120.9 (6)	C21—C20—C19	116.7 (7)
N1—C4—C3	119.2 (5)	C21—C20—H20	121.6
C5—C4—C3	119.9 (5)	C19—C20—H20	121.6
C6—C5—C4	120.3 (6)	O2—C21—C20	119.9 (5)
C6—C5—H5	119.9	O2—C21—C22	120.3 (4)
C4—C5—H5	119.9	C20—C21—C22	119.8 (5)
C5—C6—C7	120.9 (5)	N2—C22—C21	118.0 (4)
C5—C6—H6	119.6	N2—C22—C17	119.8 (6)
C7—C6—H6	119.6	C21—C22—C17	122.2 (6)
C8—C7—C6	124.6 (6)

O2—Sn1—O1—C11	178.2 (3)	Sn1—O1—C11—C12	5.6 (5)
C2—Sn1—O1—C11	76.3 (3)	C9—C10—C11—O1	−178.1 (5)
C1—Sn1—O1—C11	−84.4 (3)	C9—C10—C11—C12	0.8 (7)
N1—Sn1—O1—C11	−5.0 (3)	C4—N1—C12—C7	−2.0 (6)
N2—Sn1—O1—C11	168.1 (3)	Sn1—N1—C12—C7	178.5 (3)
O1—Sn1—O2—C21	−178.9 (3)	C4—N1—C12—C11	176.8 (4)
C2—Sn1—O2—C21	−81.2 (3)	Sn1—N1—C12—C11	−2.8 (4)
C1—Sn1—O2—C21	77.6 (3)	C8—C7—C12—N1	179.9 (4)
N1—Sn1—O2—C21	174.0 (3)	C6—C7—C12—N1	0.9 (6)
N2—Sn1—O2—C21	−3.6 (3)	C8—C7—C12—C11	1.2 (7)
O2—Sn1—N1—C4	−168.1 (4)	C6—C7—C12—C11	−177.8 (4)
O1—Sn1—N1—C4	−175.5 (4)	O1—C11—C12—N1	−1.0 (6)
C2—Sn1—N1—C4	83.0 (4)	C10—C11—C12—N1	−179.9 (4)
C1—Sn1—N1—C4	−68.5 (4)	O1—C11—C12—C7	177.8 (4)
N2—Sn1—N1—C4	8.7 (5)	C10—C11—C12—C7	−1.1 (6)
O2—Sn1—N1—C12	11.4 (4)	C22—N2—C14—C15	1.2 (8)
O1—Sn1—N1—C12	4.0 (2)	Sn1—N2—C14—C15	179.9 (4)
C2—Sn1—N1—C12	−97.5 (3)	C22—N2—C14—C13	179.8 (5)
C1—Sn1—N1—C12	111.0 (3)	Sn1—N2—C14—C13	−1.5 (7)
N2—Sn1—N1—C12	−171.8 (2)	N2—C14—C15—C16	−1.4 (10)
O2—Sn1—N2—C14	−177.6 (4)	C13—C14—C15—C16	−180.0 (7)
O1—Sn1—N2—C14	−167.0 (4)	C14—C15—C16—C17	1.7 (12)
C2—Sn1—N2—C14	−71.3 (4)	C15—C16—C17—C18	178.6 (8)
C1—Sn1—N2—C14	81.1 (4)	C15—C16—C17—C22	−1.7 (9)
N1—Sn1—N2—C14	3.9 (5)	C16—C17—C18—C19	−177.9 (7)
O2—Sn1—N2—C22	1.3 (3)	C22—C17—C18—C19	2.4 (11)
O1—Sn1—N2—C22	11.9 (4)	C17—C18—C19—C20	−2.6 (12)
C2—Sn1—N2—C22	107.6 (3)	C18—C19—C20—C21	0.2 (9)
C1—Sn1—N2—C22	−100.0 (3)	Sn1—O2—C21—C20	−175.0 (3)
N1—Sn1—N2—C22	−177.2 (2)	Sn1—O2—C21—C22	5.7 (5)
C12—N1—C4—C5	1.4 (7)	C19—C20—C21—O2	−177.4 (4)
Sn1—N1—C4—C5	−179.1 (3)	C19—C20—C21—C22	1.9 (7)
C12—N1—C4—C3	−179.2 (4)	C14—N2—C22—C21	179.9 (4)
Sn1—N1—C4—C3	0.3 (7)	Sn1—N2—C22—C21	0.9 (4)
N1—C4—C5—C6	0.1 (8)	C14—N2—C22—C17	−1.2 (7)
C3—C4—C5—C6	−179.3 (5)	Sn1—N2—C22—C17	179.7 (3)
C4—C5—C6—C7	−1.2 (8)	O2—C21—C22—N2	−4.0 (6)
C5—C6—C7—C8	−178.3 (5)	C20—C21—C22—N2	176.7 (4)
C5—C6—C7—C12	0.6 (7)	O2—C21—C22—C17	177.2 (4)
C6—C7—C8—C9	178.0 (6)	C20—C21—C22—C17	−2.1 (7)
C12—C7—C8—C9	−0.9 (8)	C18—C17—C22—N2	−178.8 (5)
C7—C8—C9—C10	0.7 (10)	C16—C17—C22—N2	1.4 (7)
C8—C9—C10—C11	−0.6 (9)	C18—C17—C22—C21	0.0 (8)
Sn1—O1—C11—C10	−175.5 (3)	C16—C17—C22—C21	−179.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3C···O2ⁱ	0.96	2.49	3.353 (7)	149

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Sn(CH₃)₂(C₁₀H₈NO)₂]
M_r	465.11
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	8.0434 (4), 20.6952 (10), 12.0102 (6)
β (°)	95.420 (5)
V (Å³)	1990.28 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.30
Crystal size (mm)	0.25 × 0.25 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.737, 0.938
No. of measured, independent and observed [I > 2σ(I)] reflections	20963, 4600, 3410
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.094, 1.05
No. of reflections	4600
No. of parameters	246
No. of restraints	30
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.79, −0.49

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3C···O2ⁱ	0.96	2.49	3.353 (7)	149

Symmetry code: (i) x−1, y, z.

Acknowledgements

The authors thank Shahid Beheshti University and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Das, V. G., Chen, W., Yap, C. K. & Sinn, E. (1984). Chem. Commun. pp. 1418–1419. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar