Dimeth­yl[2-oxido-1-naphthaldehyde (4-hydroxy­lbenzo­yl)hydrazonato]tin(IV) dichloro­methane solvate

Cui, J.; Yin, H.; Qiao, Y.

doi:10.1107/S1600536807060102

Dimethyl[2-oxido-1-naphthaldehyde (4-hydroxylbenzoyl)hydrazonato]tin(IV) dichloromethane solvate

In the molecular structure of the title complex, [Sn(CH₃)₂(C₁₈H₁₂N₂O₃)]·CH₂Cl₂, the Sn atom is in a distorted trigonal–bipyramidal environment, with Sn—O distances of 2.083 (3) and 2.143 (2) Å. In the crystal structure, the molecules are stabilized by intermolecular O—H

N hydrogen bonds, giving rise to the formation of one-dimensional chains.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060102/su2025sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060102/su2025Isup2.hkl Contains datablock I

CCDC reference: 672742

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R factor = 0.029
wR factor = 0.087
Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT410_ALERT_2_C Short Intra H...H Contact  H1     ..  H8      ..       1.98 Ang.
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H10    ..  H20A    ..       2.11 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The molecular structure of the title compound, (I), is shown in Fig. 1. The Sn atom has a distorted trigonal-bipyramidal geometry, with atoms O1 and O3 in axial positions [O1—Sn1—O2 = 154.97 (10)°], and atoms C19, C20 and N1 in equatorial positions. The sum of the equatorial angles C19—Sn1—C20, C19—Sn1—N1 and C20—Sn—N1 is 359.92 °, indicating approximate coplanarity for these atoms (Table 1). The Sn1—N1 bond length of 2.166 (3) Å is close to the sum of the non-polar covalent radii [2.15 Å], indicating a strong Sn—N interaction. The O atoms coordinate to the Sn atom with one short [2.083 (3) Å] and one long [2.143 (2) Å] bond. These distances are similar to those reported for compound [Sn(C₆H₅)₂(C₁₄H₁₀N₂O₃)]·C₂H₆O (M. Hong et al., 2006)

The crystal packing in the unit cell (Fig. 2) shows that symmetry related molecules are connected by intermolecular O—H···N hydrogen bonds to form one-dimensional chains (Table 2).

Related literature top

For the structure of a similar compound, [Sn(C₆H₅)₂(C₁₄H₁₀N₂O₃)]·C₂H₆O, see: Hong et al. (2006).

Experimental top

The reaction was carried out under a nitrogen atmosphere. 2-hydroxy-1-naphthaldehyde 4-hydroxybenzhydrazone (1 mmol) and sodium ethoxide (1.2 mmol) were added to 30 ml of benzene in a Schlenk flask and stirred for 0.5 h. Dimethyltin dichloride (1 mmol) was then added and the mixture stirred for 4 h at 313 K. The resulting clear solution was evaporated under vacuum. The product was crystallized from a mixture of dichloromethane/methanol (1:1). Analysis calculated for C₂₁H₂₀Cl₂N₂O₃Sn (Mr = 538.01): C, 46.88; H, 3.75; N, 5.21, found: C, 46.75; H, 3.70; N, 5.34.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (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. The molecular structure of complex (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. H atoms have been omitted for clarity.
	Fig. 2. The crystal packing of the complex (I), showing the hydrogen bonds as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

Dimethyl[2-oxido-1-naphthaldehyde (4-hydroxylbenzoyl)hydrazonato]tin(IV) dichloromethane solvate top

Crystal data top

[Sn(CH₃)₂(C₁₈H₁₂N₂O₃)]·CH₂Cl₂	F(000) = 1072
M_r = 537.98	D_x = 1.651 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5069 reflections
a = 11.982 (2) Å	θ = 2.3–27.1°
b = 9.5097 (18) Å	µ = 1.45 mm⁻¹
c = 19.546 (4) Å	T = 298 K
β = 103.695 (2)°	Block, orange
V = 2163.9 (7) Å³	0.55 × 0.41 × 0.29 mm
Z = 4

Data collection top

Siemens SMART CCD area-detector diffractometer	3777 independent reflections
Radiation source: fine-focus sealed tube	3000 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
phi and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→14
T_min = 0.502, T_max = 0.678	k = −11→10
10791 measured reflections	l = −23→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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0484P)² + 1.2287P] where P = (F_o² + 2F_c²)/3
3777 reflections	(Δ/σ)_max = 0.001
262 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

[Sn(CH₃)₂(C₁₈H₁₂N₂O₃)]·CH₂Cl₂	V = 2163.9 (7) Å³
M_r = 537.98	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.982 (2) Å	µ = 1.45 mm⁻¹
b = 9.5097 (18) Å	T = 298 K
c = 19.546 (4) Å	0.55 × 0.41 × 0.29 mm
β = 103.695 (2)°

Data collection top

Siemens SMART CCD area-detector diffractometer	3777 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3000 reflections with I > 2σ(I)
T_min = 0.502, T_max = 0.678	R_int = 0.035
10791 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 1.00	Δρ_max = 0.58 e Å⁻³
3777 reflections	Δρ_min = −0.63 e Å⁻³
262 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.69105 (2)	0.12092 (3)	1.031909 (12)	0.03692 (11)
Cl1	0.48588 (13)	0.75043 (17)	0.18170 (7)	0.0890 (4)
Cl2	0.67495 (19)	0.5571 (2)	0.18748 (11)	0.1248 (7)
N1	0.8191 (2)	0.1238 (3)	0.97009 (13)	0.0334 (7)
N2	0.7961 (2)	0.0389 (3)	0.90942 (14)	0.0340 (7)
O1	0.8042 (2)	0.2621 (3)	1.09417 (14)	0.0538 (8)
O2	0.6263 (2)	−0.0054 (3)	0.94030 (13)	0.0436 (6)
O3	0.5513 (2)	−0.4064 (3)	0.67608 (13)	0.0416 (6)
H3	0.6052	−0.4350	0.6607	0.062*
C1	0.9167 (3)	0.1905 (4)	0.98265 (18)	0.0344 (8)
H1	0.9620	0.1750	0.9507	0.041*
C2	0.9629 (3)	0.2840 (4)	1.03904 (17)	0.0332 (8)
C3	0.9035 (3)	0.3163 (4)	1.09172 (19)	0.0376 (8)
C4	0.9531 (3)	0.4126 (4)	1.1455 (2)	0.0429 (9)
H4	0.9132	0.4363	1.1792	0.051*
C5	1.0565 (3)	0.4709 (4)	1.14893 (19)	0.0415 (9)
H5	1.0868	0.5322	1.1857	0.050*
C6	1.1205 (3)	0.4416 (4)	1.09835 (19)	0.0361 (8)
C7	1.0735 (3)	0.3485 (3)	1.04206 (18)	0.0322 (8)
C8	1.1405 (3)	0.3236 (5)	0.9928 (2)	0.0473 (10)
H8	1.1117	0.2658	0.9543	0.057*
C9	1.2465 (4)	0.3825 (5)	1.0005 (2)	0.0532 (11)
H9	1.2887	0.3635	0.9673	0.064*
C10	1.2928 (4)	0.4705 (4)	1.0569 (2)	0.0525 (11)
H10	1.3658	0.5084	1.0619	0.063*
C11	1.2306 (3)	0.5003 (4)	1.1045 (2)	0.0449 (9)
H11	1.2608	0.5604	1.1419	0.054*
C12	0.6966 (3)	−0.0228 (4)	0.89995 (17)	0.0314 (8)
C13	0.6610 (3)	−0.1220 (3)	0.83962 (17)	0.0315 (7)
C14	0.5467 (3)	−0.1606 (4)	0.81672 (18)	0.0379 (9)
H14	0.4929	−0.1227	0.8389	0.045*
C15	0.5108 (3)	−0.2539 (4)	0.76193 (18)	0.0376 (8)
H15	0.4335	−0.2773	0.7470	0.045*
C16	0.5909 (3)	−0.3127 (4)	0.72916 (17)	0.0326 (8)
C17	0.7056 (3)	−0.2758 (4)	0.75147 (17)	0.0334 (8)
H17	0.7595	−0.3153	0.7299	0.040*
C18	0.7399 (3)	−0.1811 (4)	0.80529 (18)	0.0343 (8)
H18	0.8169	−0.1558	0.8192	0.041*
C19	0.7199 (4)	−0.0443 (5)	1.1064 (2)	0.0606 (12)
H19A	0.7891	−0.0933	1.1043	0.091*
H19B	0.6563	−0.1085	1.0959	0.091*
H19C	0.7274	−0.0063	1.1528	0.091*
C20	0.5496 (3)	0.2591 (4)	1.0161 (2)	0.0506 (10)
H20A	0.5543	0.3256	0.9800	0.076*
H20B	0.5506	0.3083	1.0592	0.076*
H20C	0.4796	0.2063	1.0021	0.076*
C21	0.5843 (6)	0.6352 (6)	0.2328 (3)	0.095 (2)
H21A	0.6301	0.6862	0.2726	0.114*
H21B	0.5427	0.5623	0.2510	0.114*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.03455 (16)	0.04512 (18)	0.03349 (15)	−0.00971 (11)	0.01285 (11)	−0.00709 (11)
Cl1	0.0785 (10)	0.1087 (12)	0.0733 (8)	0.0103 (8)	0.0050 (7)	−0.0048 (8)
Cl2	0.1263 (16)	0.1530 (17)	0.1148 (14)	0.0467 (14)	0.0675 (12)	0.0267 (13)
N1	0.0377 (17)	0.0354 (17)	0.0292 (14)	−0.0092 (13)	0.0118 (13)	−0.0069 (12)
N2	0.0364 (17)	0.0380 (17)	0.0280 (14)	−0.0083 (13)	0.0089 (13)	−0.0077 (12)
O1	0.0437 (16)	0.073 (2)	0.0493 (15)	−0.0244 (15)	0.0208 (13)	−0.0268 (15)
O2	0.0368 (14)	0.0573 (17)	0.0403 (14)	−0.0180 (13)	0.0164 (12)	−0.0172 (13)
O3	0.0390 (15)	0.0496 (16)	0.0367 (13)	−0.0041 (12)	0.0101 (11)	−0.0129 (12)
C1	0.0289 (19)	0.039 (2)	0.0370 (18)	−0.0049 (16)	0.0116 (15)	−0.0013 (16)
C2	0.0305 (19)	0.0351 (19)	0.0321 (17)	−0.0005 (15)	0.0039 (15)	−0.0008 (15)
C3	0.033 (2)	0.041 (2)	0.0395 (19)	−0.0044 (17)	0.0109 (16)	−0.0063 (16)
C4	0.041 (2)	0.048 (2)	0.040 (2)	−0.0049 (18)	0.0113 (17)	−0.0133 (17)
C5	0.042 (2)	0.038 (2)	0.041 (2)	−0.0043 (17)	0.0037 (17)	−0.0075 (16)
C6	0.035 (2)	0.0258 (18)	0.042 (2)	−0.0033 (15)	−0.0009 (16)	0.0030 (15)
C7	0.0312 (18)	0.0283 (18)	0.0344 (17)	0.0018 (15)	0.0027 (15)	0.0053 (14)
C8	0.041 (2)	0.057 (3)	0.044 (2)	−0.0080 (19)	0.0109 (18)	−0.0068 (19)
C9	0.038 (2)	0.066 (3)	0.060 (3)	−0.004 (2)	0.020 (2)	−0.003 (2)
C10	0.038 (2)	0.054 (3)	0.064 (3)	−0.016 (2)	0.009 (2)	0.004 (2)
C11	0.038 (2)	0.041 (2)	0.052 (2)	−0.0076 (17)	0.0029 (19)	0.0002 (19)
C12	0.0326 (19)	0.0326 (19)	0.0293 (17)	−0.0019 (15)	0.0078 (15)	0.0018 (14)
C13	0.0341 (19)	0.0301 (18)	0.0292 (16)	−0.0038 (15)	0.0057 (14)	0.0046 (14)
C14	0.036 (2)	0.047 (2)	0.0358 (18)	−0.0066 (17)	0.0173 (16)	−0.0112 (16)
C15	0.0292 (19)	0.046 (2)	0.0375 (18)	−0.0079 (16)	0.0087 (15)	−0.0061 (17)
C16	0.0353 (19)	0.0326 (19)	0.0293 (17)	−0.0009 (15)	0.0063 (15)	0.0005 (14)
C17	0.033 (2)	0.035 (2)	0.0331 (17)	0.0032 (15)	0.0093 (15)	−0.0008 (15)
C18	0.0287 (18)	0.0341 (19)	0.0380 (18)	−0.0020 (15)	0.0040 (15)	0.0019 (15)
C19	0.074 (3)	0.059 (3)	0.050 (2)	−0.005 (2)	0.016 (2)	0.004 (2)
C20	0.045 (2)	0.054 (3)	0.057 (2)	−0.002 (2)	0.019 (2)	−0.002 (2)
C21	0.121 (6)	0.093 (4)	0.083 (4)	0.028 (4)	0.049 (4)	0.017 (3)

Geometric parameters (Å, º) top

Sn1—O1	2.083 (3)	C8—C9	1.364 (6)
Sn1—O2	2.143 (2)	C8—H8	0.9300
Sn1—N1	2.166 (3)	C9—C10	1.391 (6)
Sn1—C20	2.109 (4)	C9—H9	0.9300
Sn1—C19	2.114 (4)	C10—C11	1.353 (6)
Cl1—C21	1.741 (6)	C10—H10	0.9300
Cl2—C21	1.723 (6)	C11—H11	0.9300
N1—C1	1.302 (4)	C12—C13	1.492 (5)
N1—N2	1.407 (4)	C13—C14	1.386 (5)
N2—C12	1.302 (4)	C13—C18	1.400 (5)
O1—C3	1.308 (4)	C14—C15	1.378 (5)
O2—C12	1.294 (4)	C14—H14	0.9300
O3—C16	1.365 (4)	C15—C16	1.391 (5)
O3—H3	0.8200	C15—H15	0.9300
C1—C2	1.422 (5)	C16—C17	1.384 (5)
C1—H1	0.9300	C17—C18	1.372 (5)
C2—C3	1.417 (5)	C17—H17	0.9300
C2—C7	1.450 (5)	C18—H18	0.9300
C3—C4	1.414 (5)	C19—H19A	0.9600
C4—C5	1.343 (5)	C19—H19B	0.9600
C4—H4	0.9300	C19—H19C	0.9600
C5—C6	1.415 (5)	C20—H20A	0.9600
C5—H5	0.9300	C20—H20B	0.9600
C6—C11	1.411 (5)	C20—H20C	0.9600
C6—C7	1.420 (5)	C21—H21A	0.9700
C7—C8	1.411 (5)	C21—H21B	0.9700

O1—Sn1—C20	94.20 (15)	C11—C10—H10	120.3
O1—Sn1—C19	95.68 (15)	C9—C10—H10	120.3
C20—Sn1—C19	123.96 (18)	C10—C11—C6	120.9 (4)
O1—Sn1—O2	154.97 (10)	C10—C11—H11	119.5
C20—Sn1—O2	96.18 (14)	C6—C11—H11	119.5
C19—Sn1—O2	97.27 (15)	O2—C12—N2	124.2 (3)
O1—Sn1—N1	82.46 (10)	O2—C12—C13	117.2 (3)
C20—Sn1—N1	124.14 (14)	N2—C12—C13	118.6 (3)
C19—Sn1—N1	111.82 (16)	C14—C13—C18	117.8 (3)
O2—Sn1—N1	72.86 (9)	C14—C13—C12	119.9 (3)
C1—N1—N2	115.2 (3)	C18—C13—C12	122.3 (3)
C1—N1—Sn1	128.6 (2)	C15—C14—C13	121.6 (3)
N2—N1—Sn1	116.09 (19)	C15—C14—H14	119.2
C12—N2—N1	111.6 (3)	C13—C14—H14	119.2
C3—O1—Sn1	134.8 (2)	C14—C15—C16	119.6 (3)
C12—O2—Sn1	114.9 (2)	C14—C15—H15	120.2
C16—O3—H3	109.5	C16—C15—H15	120.2
N1—C1—C2	128.1 (3)	O3—C16—C17	123.1 (3)
N1—C1—H1	115.9	O3—C16—C15	117.3 (3)
C2—C1—H1	115.9	C17—C16—C15	119.6 (3)
C3—C2—C1	121.9 (3)	C18—C17—C16	120.2 (3)
C3—C2—C7	119.4 (3)	C18—C17—H17	119.9
C1—C2—C7	118.7 (3)	C16—C17—H17	119.9
O1—C3—C4	117.0 (3)	C17—C18—C13	121.1 (3)
O1—C3—C2	123.9 (3)	C17—C18—H18	119.4
C4—C3—C2	119.0 (3)	C13—C18—H18	119.4
C5—C4—C3	121.6 (4)	Sn1—C19—H19A	109.5
C5—C4—H4	119.2	Sn1—C19—H19B	109.5
C3—C4—H4	119.2	H19A—C19—H19B	109.5
C4—C5—C6	122.0 (3)	Sn1—C19—H19C	109.5
C4—C5—H5	119.0	H19A—C19—H19C	109.5
C6—C5—H5	119.0	H19B—C19—H19C	109.5
C11—C6—C5	120.8 (3)	Sn1—C20—H20A	109.5
C11—C6—C7	120.2 (4)	Sn1—C20—H20B	109.5
C5—C6—C7	118.9 (3)	H20A—C20—H20B	109.5
C8—C7—C6	116.6 (3)	Sn1—C20—H20C	109.5
C8—C7—C2	124.3 (3)	H20A—C20—H20C	109.5
C6—C7—C2	119.1 (3)	H20B—C20—H20C	109.5
C9—C8—C7	121.4 (4)	Cl2—C21—Cl1	113.6 (3)
C9—C8—H8	119.3	Cl2—C21—H21A	108.8
C7—C8—H8	119.3	Cl1—C21—H21A	108.8
C8—C9—C10	121.3 (4)	Cl2—C21—H21B	108.8
C8—C9—H9	119.3	Cl1—C21—H21B	108.8
C10—C9—H9	119.3	H21A—C21—H21B	107.7
C11—C10—C9	119.4 (4)

O1—Sn1—N1—C1	2.6 (3)	C11—C6—C7—C8	−2.2 (5)
C20—Sn1—N1—C1	92.6 (3)	C5—C6—C7—C8	179.6 (3)
C19—Sn1—N1—C1	−90.5 (3)	C11—C6—C7—C2	176.8 (3)
O2—Sn1—N1—C1	178.4 (3)	C5—C6—C7—C2	−1.4 (5)
O1—Sn1—N1—N2	−179.8 (2)	C3—C2—C7—C8	179.7 (4)
C20—Sn1—N1—N2	−89.8 (3)	C1—C2—C7—C8	−0.8 (5)
C19—Sn1—N1—N2	87.1 (3)	C3—C2—C7—C6	0.7 (5)
O2—Sn1—N1—N2	−4.0 (2)	C1—C2—C7—C6	−179.7 (3)
C1—N1—N2—C12	−179.2 (3)	C6—C7—C8—C9	2.1 (6)
Sn1—N1—N2—C12	2.8 (4)	C2—C7—C8—C9	−176.8 (4)
C20—Sn1—O1—C3	−124.8 (4)	C7—C8—C9—C10	−0.5 (7)
C19—Sn1—O1—C3	110.5 (4)	C8—C9—C10—C11	−1.2 (7)
O2—Sn1—O1—C3	−10.4 (6)	C9—C10—C11—C6	1.1 (6)
N1—Sn1—O1—C3	−0.9 (4)	C5—C6—C11—C10	178.8 (4)
O1—Sn1—O2—C12	14.6 (4)	C7—C6—C11—C10	0.6 (6)
C20—Sn1—O2—C12	128.6 (3)	Sn1—O2—C12—N2	−5.3 (4)
C19—Sn1—O2—C12	−106.0 (3)	Sn1—O2—C12—C13	173.7 (2)
N1—Sn1—O2—C12	4.7 (2)	N1—N2—C12—O2	1.6 (5)
N2—N1—C1—C2	179.4 (3)	N1—N2—C12—C13	−177.3 (3)
Sn1—N1—C1—C2	−2.9 (6)	O2—C12—C13—C14	17.9 (5)
N1—C1—C2—C3	0.5 (6)	N2—C12—C13—C14	−163.1 (3)
N1—C1—C2—C7	−179.1 (3)	O2—C12—C13—C18	−160.8 (3)
Sn1—O1—C3—C4	179.3 (3)	N2—C12—C13—C18	18.2 (5)
Sn1—O1—C3—C2	−0.8 (6)	C18—C13—C14—C15	−0.1 (5)
C1—C2—C3—O1	1.5 (6)	C12—C13—C14—C15	−178.9 (3)
C7—C2—C3—O1	−179.0 (3)	C13—C14—C15—C16	0.9 (6)
C1—C2—C3—C4	−178.6 (3)	C14—C15—C16—O3	178.8 (3)
C7—C2—C3—C4	1.0 (5)	C14—C15—C16—C17	−0.7 (5)
O1—C3—C4—C5	177.9 (4)	O3—C16—C17—C18	−179.8 (3)
C2—C3—C4—C5	−2.0 (6)	C15—C16—C17—C18	−0.4 (5)
C3—C4—C5—C6	1.3 (6)	C16—C17—C18—C13	1.2 (5)
C4—C5—C6—C11	−177.8 (4)	C14—C13—C18—C17	−1.0 (5)
C4—C5—C6—C7	0.4 (6)	C12—C13—C18—C17	177.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2ⁱ	0.82	2.03	2.802 (4)	158

Symmetry code: (i) −x+3/2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Sn(CH₃)₂(C₁₈H₁₂N₂O₃)]·CH₂Cl₂
M_r	537.98
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	11.982 (2), 9.5097 (18), 19.546 (4)
β (°)	103.695 (2)
V (Å³)	2163.9 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.45
Crystal size (mm)	0.55 × 0.41 × 0.29

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.502, 0.678
No. of measured, independent and observed [I > 2σ(I)] reflections	10791, 3777, 3000
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.087, 1.00
No. of reflections	3777
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.63

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	2.083 (3)	Sn1—C20	2.109 (4)
Sn1—O2	2.143 (2)	Sn1—C19	2.114 (4)
Sn1—N1	2.166 (3)

O1—Sn1—C20	94.20 (15)	C19—Sn1—O2	97.27 (15)
O1—Sn1—C19	95.68 (15)	O1—Sn1—N1	82.46 (10)
C20—Sn1—C19	123.96 (18)	C20—Sn1—N1	124.14 (14)
O1—Sn1—O2	154.97 (10)	C19—Sn1—N1	111.82 (16)
C20—Sn1—O2	96.18 (14)	O2—Sn1—N1	72.86 (9)