Bis(N-benzoyl-N-phenyl­hydroxy­l­aminato-κ2O,O′)dimethyl­tin(IV)

Jiang, J.; Dong, L.; Yin, H.

doi:10.1107/S160053681102561X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page m1029

doi:10.1107/S160053681102561X

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Bis(N-benzoyl-N-phenylhydroxylaminato-κ²O,O′)dimethyltin(IV)

Jin Jiang,^a Lei Dong ^a and Handong Yin ^a ^*

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

(Received 17 June 2011; accepted 29 June 2011; online 6 July 2011)

The Sn atom in the title compound, [Sn(CH₃)₂(C₁₃H₁₀NO₂)₂], has a highly distorted octahedral coordination with the equatorial plane made up of four O atoms from two N-benzoyl-N-phenylhydroxylaminate ligands and the axial positions occupied by two methyl groups. The crystal structure is stabilized by van der Waals interactions.

Related literature

For related structures, see: Harrison et al. (1976 )

Experimental

Crystal data

[Sn(CH₃)₂(C₁₃H₁₀NO₂)₂]
M_r = 573.20
Monoclinic, P 2₁ /n
a = 13.5475 (14) Å
b = 10.3621 (11) Å
c = 19.0161 (19) Å
β = 102.128 (1)°
V = 2609.9 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.01 mm⁻¹
T = 298 K
0.45 × 0.41 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.658, T_max = 0.764
13127 measured reflections
4617 independent reflections
2999 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.118
S = 1.12
4617 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 1.34 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681102561X/bx2356sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681102561X/bx2356Isup2.hkl

checkCIF report

Comment top

Among many multidentate organic ligands, hydroxamic acids are of particular importance, because of their remarkable structural diversity and biological applications. The molecular structure of the title compound is depicted in Fig.1. The Sn atom has a highly distorted octahedral coordination, with the equatorial plane made up of four O atoms of N-phenyl-N-benzoylhydroxylamino ligand and the axial positions occupied by a two methyl groups . The crystal structure is built up by van der Waals interactions.

Related literature top

For related structures, see: Harrison et al. (1976)

Experimental top

The reaction was carried out under nitrogen atmosphere. N-phenylbenzohydroxamic acid (0.4 mmol) and KOH (0.4 mmol) were added to a stirred solution of methanol (30 ml) in a Schlenk flask for 0.5 h, then dimethyltin dichloride (0.2 mmol) was added to the reactor. The reaction mixture was stirred for 8 h at room temperature and then filtrated. The filtrate was evaporated in vacuo to dryness. The obtained solid was recrystallized from ethylether-petroleum ether (v/v, 1:1) (Yield 78%). Anal. Calcd (%) for C₂₈H₂₆N₂O₄Sn (Mr = 573.20): C, 58.67; H, 4.57; N, 4.89; O, 11.16. Found (%): C, 58.60; H, 4.51; N, 4.97; O, 11.08.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the compound, showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity.

Bis(N-benzoyl-N-phenylhydroxylaminato- κ²O,O')dimethyltin(IV) top

Crystal data top

[Sn(CH₃)₂(C₁₃H₁₀NO₂)₂]	F(000) = 1160
M_r = 573.20	D_x = 1.459 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3950 reflections
a = 13.5475 (14) Å	θ = 2.2–23.5°
b = 10.3621 (11) Å	µ = 1.01 mm⁻¹
c = 19.0161 (19) Å	T = 298 K
β = 102.128 (1)°	Block, colourless
V = 2609.9 (5) Å³	0.45 × 0.41 × 0.28 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	4617 independent reflections
Radiation source: fine-focus sealed tube	2999 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→16
T_min = 0.658, T_max = 0.764	k = −12→12
13127 measured reflections	l = −22→19

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0414P)² + 2.3713P] where P = (F_o² + 2F_c²)/3
4617 reflections	(Δ/σ)_max = 0.001
316 parameters	Δρ_max = 1.34 e Å⁻³
0 restraints	Δρ_min = −0.65 e Å⁻³

Crystal data top

[Sn(CH₃)₂(C₁₃H₁₀NO₂)₂]	V = 2609.9 (5) Å³
M_r = 573.20	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.5475 (14) Å	µ = 1.01 mm⁻¹
b = 10.3621 (11) Å	T = 298 K
c = 19.0161 (19) Å	0.45 × 0.41 × 0.28 mm
β = 102.128 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4617 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2999 reflections with I > 2σ(I)
T_min = 0.658, T_max = 0.764	R_int = 0.054
13127 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.12	Δρ_max = 1.34 e Å⁻³
4617 reflections	Δρ_min = −0.65 e Å⁻³
316 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.53023 (3)	0.21609 (4)	0.87352 (2)	0.04530 (15)
N1	0.3263 (3)	0.1438 (4)	0.7933 (2)	0.0438 (11)
N2	0.7002 (3)	0.2851 (5)	0.8049 (2)	0.0484 (11)
O1	0.4223 (2)	0.1710 (4)	0.78095 (18)	0.0548 (11)
O2	0.3965 (3)	0.1015 (4)	0.90754 (18)	0.0540 (10)
O3	0.5963 (3)	0.2700 (4)	0.7884 (2)	0.0585 (11)
O4	0.6905 (3)	0.3335 (4)	0.9179 (2)	0.0574 (10)
C1	0.2476 (4)	0.1830 (5)	0.7352 (3)	0.0427 (14)
C2	0.1697 (4)	0.2588 (6)	0.7472 (3)	0.0542 (16)
H2	0.1660	0.2826	0.7937	0.065*
C3	0.0970 (5)	0.2991 (6)	0.6893 (4)	0.0653 (18)
H3	0.0437	0.3498	0.6972	0.078*
C4	0.1015 (5)	0.2663 (7)	0.6210 (4)	0.0684 (19)
H4	0.0514	0.2935	0.5827	0.082*
C5	0.1807 (5)	0.1923 (6)	0.6088 (3)	0.0659 (19)
H5	0.1854	0.1714	0.5621	0.079*
C6	0.2531 (4)	0.1493 (6)	0.6665 (3)	0.0523 (15)
H6	0.3057	0.0973	0.6586	0.063*
C7	0.3195 (4)	0.1019 (5)	0.8581 (3)	0.0416 (13)
C8	0.2221 (4)	0.0502 (5)	0.8709 (3)	0.0418 (13)
C9	0.1598 (4)	−0.0267 (5)	0.8222 (3)	0.0477 (14)
H9	0.1740	−0.0413	0.7771	0.057*
C10	0.0757 (4)	−0.0825 (6)	0.8401 (3)	0.0545 (15)
H10	0.0333	−0.1350	0.8073	0.065*
C11	0.0555 (5)	−0.0599 (7)	0.9062 (4)	0.0704 (19)
H11	−0.0014	−0.0969	0.9181	0.084*
C12	0.1170 (5)	0.0159 (8)	0.9551 (4)	0.087 (2)
H12	0.1019	0.0313	0.9999	0.104*
C13	0.2012 (4)	0.0693 (6)	0.9380 (3)	0.0624 (17)
H13	0.2447	0.1187	0.9719	0.075*
C14	0.7473 (4)	0.2419 (5)	0.7494 (3)	0.0451 (14)
C15	0.8264 (4)	0.1561 (6)	0.7627 (3)	0.0592 (16)
H15	0.8509	0.1261	0.8092	0.071*
C16	0.8692 (5)	0.1146 (7)	0.7071 (4)	0.073 (2)
H16	0.9232	0.0573	0.7165	0.088*
C17	0.8334 (5)	0.1565 (8)	0.6389 (4)	0.078 (2)
H17	0.8633	0.1290	0.6017	0.093*
C18	0.7536 (5)	0.2390 (7)	0.6253 (4)	0.074 (2)
H18	0.7278	0.2654	0.5783	0.088*
C19	0.7100 (4)	0.2843 (6)	0.6800 (3)	0.0586 (16)
H19	0.6564	0.3423	0.6703	0.070*
C20	0.7432 (4)	0.3252 (5)	0.8716 (3)	0.0479 (14)
C21	0.8507 (4)	0.3625 (6)	0.8857 (3)	0.0497 (14)
C22	0.9129 (5)	0.3195 (7)	0.9482 (4)	0.074 (2)
H22	0.8871	0.2679	0.9802	0.089*
C23	1.0133 (5)	0.3535 (8)	0.9630 (4)	0.091 (3)
H23	1.0555	0.3248	1.0051	0.110*
C24	1.0515 (5)	0.4296 (9)	0.9159 (5)	0.098 (3)
H24	1.1196	0.4512	0.9261	0.117*
C25	0.9905 (5)	0.4736 (7)	0.8546 (4)	0.077 (2)
H25	1.0167	0.5256	0.8230	0.092*
C26	0.8897 (4)	0.4407 (6)	0.8395 (3)	0.0605 (17)
H26	0.8476	0.4714	0.7978	0.073*
C27	0.4692 (5)	0.3809 (6)	0.9127 (4)	0.074 (2)
H27A	0.4747	0.4532	0.8822	0.111*
H27B	0.5057	0.3990	0.9607	0.111*
H27C	0.3995	0.3659	0.9132	0.111*
C28	0.6163 (4)	0.0528 (6)	0.9129 (4)	0.0716 (19)
H28A	0.5905	−0.0212	0.8845	0.107*
H28B	0.6123	0.0381	0.9620	0.107*
H28C	0.6854	0.0667	0.9100	0.107*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0388 (2)	0.0544 (3)	0.0415 (2)	−0.00119 (19)	0.00566 (15)	0.0018 (2)
N1	0.035 (2)	0.060 (3)	0.036 (3)	−0.002 (2)	0.0069 (19)	0.004 (2)
N2	0.032 (2)	0.064 (3)	0.049 (3)	−0.002 (2)	0.009 (2)	0.004 (3)
O1	0.033 (2)	0.094 (3)	0.037 (2)	−0.009 (2)	0.0075 (16)	0.003 (2)
O2	0.046 (2)	0.076 (3)	0.036 (2)	−0.0099 (19)	−0.0016 (17)	0.0090 (19)
O3	0.033 (2)	0.097 (3)	0.044 (2)	−0.006 (2)	0.0044 (16)	0.011 (2)
O4	0.052 (2)	0.072 (3)	0.050 (3)	−0.009 (2)	0.0146 (19)	0.002 (2)
C1	0.033 (3)	0.055 (4)	0.039 (3)	−0.005 (2)	0.005 (2)	0.005 (3)
C2	0.050 (4)	0.062 (4)	0.052 (4)	0.005 (3)	0.014 (3)	0.004 (3)
C3	0.057 (4)	0.063 (5)	0.075 (5)	0.011 (3)	0.011 (3)	0.016 (4)
C4	0.051 (4)	0.079 (5)	0.066 (5)	−0.005 (4)	−0.009 (3)	0.020 (4)
C5	0.064 (4)	0.089 (5)	0.039 (4)	−0.014 (4)	−0.002 (3)	0.005 (3)
C6	0.044 (3)	0.068 (4)	0.043 (4)	0.005 (3)	0.006 (3)	−0.005 (3)
C7	0.035 (3)	0.050 (3)	0.040 (3)	−0.004 (2)	0.007 (2)	0.002 (3)
C8	0.043 (3)	0.050 (3)	0.032 (3)	0.004 (3)	0.009 (2)	0.002 (3)
C9	0.049 (3)	0.053 (4)	0.043 (3)	−0.005 (3)	0.014 (3)	−0.007 (3)
C10	0.048 (4)	0.062 (4)	0.052 (4)	−0.008 (3)	0.008 (3)	−0.003 (3)
C11	0.051 (4)	0.100 (6)	0.062 (4)	−0.018 (4)	0.019 (3)	−0.001 (4)
C12	0.075 (5)	0.135 (7)	0.061 (5)	−0.030 (5)	0.037 (4)	−0.026 (5)
C13	0.055 (4)	0.087 (5)	0.046 (4)	−0.012 (3)	0.012 (3)	−0.013 (3)
C14	0.031 (3)	0.053 (4)	0.050 (3)	−0.006 (2)	0.006 (2)	0.000 (3)
C15	0.058 (4)	0.057 (4)	0.059 (4)	0.005 (3)	0.005 (3)	0.003 (3)
C16	0.058 (4)	0.076 (5)	0.089 (6)	0.012 (4)	0.021 (4)	−0.009 (4)
C17	0.069 (5)	0.095 (6)	0.078 (6)	−0.015 (4)	0.034 (4)	−0.018 (5)
C18	0.075 (5)	0.096 (6)	0.051 (4)	−0.009 (4)	0.017 (4)	0.002 (4)
C19	0.048 (3)	0.074 (4)	0.055 (4)	0.008 (3)	0.013 (3)	0.012 (3)
C20	0.039 (3)	0.050 (4)	0.054 (4)	−0.002 (3)	0.010 (3)	0.007 (3)
C21	0.044 (3)	0.050 (4)	0.053 (4)	−0.002 (3)	0.006 (3)	−0.003 (3)
C22	0.056 (4)	0.087 (5)	0.071 (5)	−0.008 (4)	−0.002 (3)	0.011 (4)
C23	0.050 (4)	0.113 (6)	0.095 (6)	−0.009 (4)	−0.021 (4)	0.015 (5)
C24	0.042 (4)	0.126 (7)	0.118 (7)	−0.024 (4)	0.000 (4)	−0.003 (6)
C25	0.060 (4)	0.089 (5)	0.082 (5)	−0.021 (4)	0.013 (4)	0.003 (4)
C26	0.051 (4)	0.063 (4)	0.067 (4)	−0.008 (3)	0.011 (3)	−0.001 (3)
C27	0.067 (4)	0.065 (5)	0.097 (5)	−0.002 (3)	0.031 (4)	−0.009 (4)
C28	0.050 (4)	0.061 (4)	0.098 (5)	0.004 (3)	0.004 (3)	0.015 (4)

Geometric parameters (Å, º) top

Sn1—O3	2.083 (4)	C11—H11	0.9300
Sn1—O1	2.091 (3)	C12—C13	1.367 (8)
Sn1—C28	2.101 (6)	C12—H12	0.9300
Sn1—C27	2.101 (6)	C13—H13	0.9300
Sn1—O2	2.367 (4)	C14—C15	1.374 (8)
Sn1—O4	2.477 (4)	C14—C19	1.383 (8)
N1—C7	1.328 (6)	C15—C16	1.377 (9)
N1—O1	1.398 (5)	C15—H15	0.9300
N1—C1	1.425 (6)	C16—C17	1.358 (9)
N2—C20	1.345 (7)	C16—H16	0.9300
N2—O3	1.385 (5)	C17—C18	1.360 (9)
N2—C14	1.415 (7)	C17—H17	0.9300
O2—C7	1.249 (5)	C18—C19	1.382 (9)
O4—C20	1.247 (6)	C18—H18	0.9300
C1—C6	1.370 (7)	C19—H19	0.9300
C1—C2	1.373 (7)	C20—C21	1.476 (7)
C2—C3	1.379 (8)	C21—C22	1.379 (8)
C2—H2	0.9300	C21—C26	1.379 (8)
C3—C4	1.355 (9)	C22—C23	1.376 (9)
C3—H3	0.9300	C22—H22	0.9300
C4—C5	1.377 (9)	C23—C24	1.374 (10)
C4—H4	0.9300	C23—H23	0.9300
C5—C6	1.382 (7)	C24—C25	1.358 (10)
C5—H5	0.9300	C24—H24	0.9300
C6—H6	0.9300	C25—C26	1.379 (8)
C7—C8	1.491 (7)	C25—H25	0.9300
C8—C9	1.369 (7)	C26—H26	0.9300
C8—C13	1.378 (7)	C27—H27A	0.9600
C9—C10	1.382 (7)	C27—H27B	0.9600
C9—H9	0.9300	C27—H27C	0.9600
C10—C11	1.361 (8)	C28—H28A	0.9600
C10—H10	0.9300	C28—H28B	0.9600
C11—C12	1.362 (8)	C28—H28C	0.9600

O3—Sn1—O1	75.22 (13)	C11—C12—C13	119.5 (6)
O3—Sn1—C28	101.3 (2)	C11—C12—H12	120.2
O1—Sn1—C28	110.9 (2)	C13—C12—H12	120.2
O3—Sn1—C27	108.8 (2)	C12—C13—C8	120.4 (6)
O1—Sn1—C27	102.9 (2)	C12—C13—H13	119.8
C28—Sn1—C27	139.3 (3)	C8—C13—H13	119.8
O3—Sn1—O2	145.61 (13)	C15—C14—C19	119.7 (6)
O1—Sn1—O2	71.21 (13)	C15—C14—N2	121.6 (5)
C28—Sn1—O2	84.1 (2)	C19—C14—N2	118.7 (5)
C27—Sn1—O2	86.0 (2)	C14—C15—C16	120.0 (6)
O3—Sn1—O4	69.15 (13)	C14—C15—H15	120.0
O1—Sn1—O4	143.55 (13)	C16—C15—H15	120.0
C28—Sn1—O4	83.89 (19)	C17—C16—C15	120.7 (6)
C27—Sn1—O4	82.0 (2)	C17—C16—H16	119.7
O2—Sn1—O4	145.05 (12)	C15—C16—H16	119.7
C7—N1—O1	118.1 (4)	C16—C17—C18	119.5 (7)
C7—N1—C1	128.8 (4)	C16—C17—H17	120.3
O1—N1—C1	112.5 (4)	C18—C17—H17	120.3
C20—N2—O3	117.8 (4)	C17—C18—C19	121.3 (7)
C20—N2—C14	128.8 (4)	C17—C18—H18	119.3
O3—N2—C14	113.0 (4)	C19—C18—H18	119.3
N1—O1—Sn1	114.4 (3)	C18—C19—C14	118.8 (6)
C7—O2—Sn1	111.1 (3)	C18—C19—H19	120.6
N2—O3—Sn1	115.9 (3)	C14—C19—H19	120.6
C20—O4—Sn1	108.4 (3)	O4—C20—N2	119.2 (5)
C6—C1—C2	120.2 (5)	O4—C20—C21	122.9 (5)
C6—C1—N1	119.1 (5)	N2—C20—C21	117.8 (5)
C2—C1—N1	120.7 (5)	C22—C21—C26	119.5 (6)
C1—C2—C3	119.0 (6)	C22—C21—C20	118.2 (6)
C1—C2—H2	120.5	C26—C21—C20	122.3 (5)
C3—C2—H2	120.5	C23—C22—C21	119.5 (7)
C4—C3—C2	121.4 (6)	C23—C22—H22	120.3
C4—C3—H3	119.3	C21—C22—H22	120.3
C2—C3—H3	119.3	C24—C23—C22	120.4 (7)
C3—C4—C5	119.6 (6)	C24—C23—H23	119.8
C3—C4—H4	120.2	C22—C23—H23	119.8
C5—C4—H4	120.2	C25—C24—C23	120.5 (7)
C4—C5—C6	119.6 (6)	C25—C24—H24	119.7
C4—C5—H5	120.2	C23—C24—H24	119.7
C6—C5—H5	120.2	C24—C25—C26	119.5 (7)
C1—C6—C5	120.1 (6)	C24—C25—H25	120.2
C1—C6—H6	119.9	C26—C25—H25	120.2
C5—C6—H6	119.9	C25—C26—C21	120.6 (6)
O2—C7—N1	119.2 (5)	C25—C26—H26	119.7
O2—C7—C8	120.3 (5)	C21—C26—H26	119.7
N1—C7—C8	120.4 (4)	Sn1—C27—H27A	109.5
C9—C8—C13	119.5 (5)	Sn1—C27—H27B	109.5
C9—C8—C7	122.7 (5)	H27A—C27—H27B	109.5
C13—C8—C7	117.4 (5)	Sn1—C27—H27C	109.5
C8—C9—C10	120.0 (5)	H27A—C27—H27C	109.5
C8—C9—H9	120.0	H27B—C27—H27C	109.5
C10—C9—H9	120.0	Sn1—C28—H28A	109.5
C11—C10—C9	119.4 (5)	Sn1—C28—H28B	109.5
C11—C10—H10	120.3	H28A—C28—H28B	109.5
C9—C10—H10	120.3	Sn1—C28—H28C	109.5
C10—C11—C12	121.1 (6)	H28A—C28—H28C	109.5
C10—C11—H11	119.4	H28B—C28—H28C	109.5
C12—C11—H11	119.4

C7—N1—O1—Sn1	−24.6 (6)	O2—C7—C8—C9	−137.2 (6)
C1—N1—O1—Sn1	147.3 (3)	N1—C7—C8—C9	40.0 (8)
O3—Sn1—O1—N1	−166.9 (4)	O2—C7—C8—C13	35.0 (8)
C28—Sn1—O1—N1	96.5 (4)	N1—C7—C8—C13	−147.7 (6)
C27—Sn1—O1—N1	−60.5 (4)	C13—C8—C9—C10	1.2 (8)
O2—Sn1—O1—N1	20.7 (3)	C7—C8—C9—C10	173.3 (5)
O4—Sn1—O1—N1	−154.5 (3)	C8—C9—C10—C11	0.2 (9)
O3—Sn1—O2—C7	−30.5 (5)	C9—C10—C11—C12	−0.5 (10)
O1—Sn1—O2—C7	−17.5 (4)	C10—C11—C12—C13	−0.7 (12)
C28—Sn1—O2—C7	−131.9 (4)	C11—C12—C13—C8	2.2 (11)
C27—Sn1—O2—C7	87.6 (4)	C9—C8—C13—C12	−2.4 (10)
O4—Sn1—O2—C7	157.6 (3)	C7—C8—C13—C12	−174.9 (6)
C20—N2—O3—Sn1	−31.1 (6)	C20—N2—C14—C15	45.2 (9)
C14—N2—O3—Sn1	142.6 (4)	O3—N2—C14—C15	−127.7 (5)
O1—Sn1—O3—N2	−161.5 (4)	C20—N2—C14—C19	−137.1 (6)
C28—Sn1—O3—N2	−52.6 (4)	O3—N2—C14—C19	50.1 (7)
C27—Sn1—O3—N2	99.7 (4)	C19—C14—C15—C16	1.2 (9)
O2—Sn1—O3—N2	−148.7 (3)	N2—C14—C15—C16	178.9 (5)
O4—Sn1—O3—N2	26.3 (3)	C14—C15—C16—C17	−0.7 (10)
O3—Sn1—O4—C20	−22.4 (4)	C15—C16—C17—C18	−0.9 (11)
O1—Sn1—O4—C20	−35.1 (5)	C16—C17—C18—C19	2.1 (11)
C28—Sn1—O4—C20	82.2 (4)	C17—C18—C19—C14	−1.6 (10)
C27—Sn1—O4—C20	−136.1 (4)	C15—C14—C19—C18	−0.1 (9)
O2—Sn1—O4—C20	152.8 (3)	N2—C14—C19—C18	−177.8 (5)
C7—N1—C1—C6	−140.5 (6)	Sn1—O4—C20—N2	14.5 (6)
O1—N1—C1—C6	48.6 (7)	Sn1—O4—C20—C21	−168.1 (4)
C7—N1—C1—C2	42.6 (8)	O3—N2—C20—O4	7.7 (8)
O1—N1—C1—C2	−128.3 (5)	C14—N2—C20—O4	−164.9 (5)
C6—C1—C2—C3	0.6 (9)	O3—N2—C20—C21	−169.9 (5)
N1—C1—C2—C3	177.5 (5)	C14—N2—C20—C21	17.6 (9)
C1—C2—C3—C4	−0.6 (9)	O4—C20—C21—C22	46.8 (8)
C2—C3—C4—C5	−0.7 (10)	N2—C20—C21—C22	−135.7 (6)
C3—C4—C5—C6	1.8 (10)	O4—C20—C21—C26	−131.6 (6)
C2—C1—C6—C5	0.6 (9)	N2—C20—C21—C26	45.9 (8)
N1—C1—C6—C5	−176.4 (5)	C26—C21—C22—C23	−1.1 (10)
C4—C5—C6—C1	−1.8 (9)	C20—C21—C22—C23	−179.5 (6)
Sn1—O2—C7—N1	10.7 (6)	C21—C22—C23—C24	0.0 (12)
Sn1—O2—C7—C8	−172.1 (4)	C22—C23—C24—C25	0.8 (14)
O1—N1—C7—O2	7.7 (8)	C23—C24—C25—C26	−0.4 (13)
C1—N1—C7—O2	−162.8 (5)	C24—C25—C26—C21	−0.7 (11)
O1—N1—C7—C8	−169.5 (4)	C22—C21—C26—C25	1.4 (10)
C1—N1—C7—C8	20.0 (8)	C20—C21—C26—C25	179.9 (6)

Experimental details

Crystal data
Chemical formula	[Sn(CH₃)₂(C₁₃H₁₀NO₂)₂]
M_r	573.20
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	13.5475 (14), 10.3621 (11), 19.0161 (19)
β (°)	102.128 (1)
V (Å³)	2609.9 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.01
Crystal size (mm)	0.45 × 0.41 × 0.28

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.658, 0.764
No. of measured, independent and observed [I > 2σ(I)] reflections	13127, 4617, 2999
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.118, 1.12
No. of reflections	4617
No. of parameters	316
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.34, −0.65

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

We acknowledge the National Natural Science Foundation of China (20771053), the National Basic Research Program (No. 2010CB234601) and the Natural Science Foundation of Shandong Province (Y2008B48) for financial support.

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Harrison, P. G., King, T. J. & Phillips, R. C. (1976). J. Chem. Soc. Dalton Trans. pp. 2317–2321. CSD CrossRef Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar