[N′-(3-Meth­oxy-2-oxidobenzyl­idene)nicotinohydrazidato]dimethyl­tin(IV)

Gao, Z.; Chen, W.; Wang, Y.; Zhao, G.

doi:10.1107/S160053680903726X

[N'-(3-Methoxy-2-oxidobenzylidene)nicotinohydrazidato]dimethyltin(IV)

In the title complex, [Sn(CH₃)₂(C₁₄H₁₁N₃O₃)], the Sn atom is in a distorted trigonal-bipyramidal coordination, with Sn-O distances of 2.138 (2) and 2.176 (2) Å. The dihedral angles between the two chelated benzene rings and the O-Sn-N group are 71.73 (9) and 83.30 (9)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680903726X/kp2231sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680903726X/kp2231Isup2.hkl Contains datablock I

CCDC reference: 750564

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Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R factor = 0.032
wR factor = 0.087
Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.07 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O3

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

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

Comment top

In the structure of the title compound, (I), (Fig. 1) the Sn1 atom is in a distored trigonal-bipyramidal coordination formed by a tridentate ligand of the azomethine N atom, the hydroxyl O atom and the carbonyl O atom (Table 1). The dihedral angles between the two chelated benzene rings: O2—Sn1—N2 and O3—Sn1—N2 are 83.30 (9) and 71.73 (9)°, respectively. The Sn atom is coordinated in distorted trigonal-bipyramidal arrangement with O2 and O3 located in the axial positions [O2—Sn1—O3 = 155.02 (9)°] and the C15, C16 and N2 in the equatorial positions. The sum of the C15—Sn1—C16 [146.08 (14)], C15—Sn1—N2 [106.13 (11)] and C16—Sn1—N2 [107.23 (11)°] bond angles is 359.44°, indicating approximate co-planarity for these atoms. Comparing the length of CN 1.270Å and C—N 1.470 Å, both bonds, C8—N2 (1.287 (4) Å) and C9—N1 (1.304 (4) Å) should be CN. The N1—N2 bond (1.400 (3) Å) is a single-bond (Yang et al., 1999). The Sn1—N2 distance is close to the sum of the covalent radii of 2.15Å (Sanderson, 1967), indicating a strong Sn—N interaction. Very similar structural parameters were observed in the compound studied by Yearwood et al. (2002).

Related literature top

For covalent radii, see: Sanderson (1967). For bond-lengh data, see: Yang et al. (1999). For a related structure, see: Yearwood et al. (2002).

Experimental top

A mixture of dimethyltin oxide (0.3295 g, 2.0 mmol) and 3-methoxy-2-oxideobenzaldehyde(3-pyridyl)methyl-hydrazone (0.5420 g, 2.0 mmol) in methanol (50 ml) was heated under reflux for 6 h. The obtained clear solution was evaporated under vacuum. The product was crystallized from a mixture of dichloromethane/ethanol (1:1) to yield blocks of (I). Yield 0.5936 g, 71%, m.p. 453 K, analysis, calculated for C₁₆H₁₇N₃O₃Sn: C 45.97, H, 4.10; N 10.06%; found: C 46.02, H 4.05, N, 10.09%.

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, 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 title complex with 30% displacement ellipsoids (H atoms omitted for clarity).

[N'-(3-Methoxy-2-oxidobenzylidene)nicotinohydrazidato]dimethyltin(IV) top

Crystal data top

[Sn(CH₃)₂(C₁₄H₁₁N₃O₃)]	F(000) = 1664
M_r = 418.02	D_x = 1.689 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4244 reflections
a = 26.121 (8) Å	θ = 2.2–27.6°
b = 9.795 (3) Å	µ = 1.57 mm⁻¹
c = 13.227 (4) Å	T = 298 K
β = 103.666 (4)°	Block, yellow
V = 3288.4 (17) Å³	0.35 × 0.16 × 0.12 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	3574 independent reflections
Radiation source: fine-focus sealed tube	3115 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −33→20
T_min = 0.609, T_max = 0.834	k = −12→12
9367 measured reflections	l = −13→16

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0558P)² + 0.5213P] where P = (F_o² + 2F_c²)/3
3574 reflections	(Δ/σ)_max < 0.001
211 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

[Sn(CH₃)₂(C₁₄H₁₁N₃O₃)]	V = 3288.4 (17) Å³
M_r = 418.02	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 26.121 (8) Å	µ = 1.57 mm⁻¹
b = 9.795 (3) Å	T = 298 K
c = 13.227 (4) Å	0.35 × 0.16 × 0.12 mm
β = 103.666 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3574 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3115 reflections with I > 2σ(I)
T_min = 0.609, T_max = 0.834	R_int = 0.023
9367 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 1.00	Δρ_max = 0.48 e Å⁻³
3574 reflections	Δρ_min = −0.54 e Å⁻³
211 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
C1	−0.17768 (17)	−0.0742 (5)	−0.0099 (5)	0.112 (2)
H1A	−0.1913	−0.0622	0.0509	0.169*
H1B	−0.1729	−0.1697	−0.0208	0.169*
H1C	−0.2021	−0.0368	−0.0693	0.169*
C2	−0.12735 (12)	0.1271 (3)	0.0369 (2)	0.0486 (7)
C3	−0.17073 (12)	0.1957 (3)	0.0522 (3)	0.0543 (8)
H3	−0.2031	0.1515	0.0391	0.065*
C4	−0.16700 (14)	0.3308 (3)	0.0870 (3)	0.0598 (9)
H4	−0.1966	0.3761	0.0973	0.072*
C5	−0.11962 (12)	0.3952 (3)	0.1057 (3)	0.0530 (7)
H5	−0.1171	0.4852	0.1286	0.064*
C6	−0.07437 (12)	0.3282 (3)	0.0910 (2)	0.0450 (7)
C7	−0.07714 (12)	0.1931 (3)	0.0542 (2)	0.0441 (7)
C8	−0.02708 (12)	0.4074 (3)	0.1159 (2)	0.0461 (6)
H8	−0.0301	0.4944	0.1421	0.055*
C9	0.10299 (11)	0.4315 (3)	0.1225 (2)	0.0453 (7)
C10	0.14890 (11)	0.5246 (3)	0.1563 (2)	0.0458 (7)
C11	0.14558 (15)	0.6528 (3)	0.1969 (3)	0.0579 (8)
H11	0.1133	0.6872	0.2032	0.069*
C12	0.19100 (16)	0.7297 (4)	0.2282 (3)	0.0701 (10)
H12	0.1898	0.8172	0.2549	0.084*
C13	0.23784 (17)	0.6734 (4)	0.2190 (3)	0.0701 (11)
H13	0.2683	0.7251	0.2416	0.084*
C14	0.19835 (12)	0.4796 (3)	0.1490 (3)	0.0563 (8)
H14	0.2006	0.3938	0.1202	0.068*
C15	0.07460 (13)	0.0606 (3)	0.1813 (2)	0.0564 (8)
H15A	0.0728	−0.0342	0.1625	0.085*
H15B	0.0544	0.0760	0.2323	0.085*
H15C	0.1106	0.0858	0.2099	0.085*
C16	0.03460 (15)	0.1988 (3)	−0.1120 (3)	0.0562 (8)
H16A	0.0649	0.2438	−0.1258	0.084*
H16B	0.0036	0.2518	−0.1405	0.084*
H16C	0.0310	0.1100	−0.1435	0.084*
N1	0.05804 (9)	0.4727 (2)	0.1381 (2)	0.0477 (6)
N2	0.01913 (9)	0.3731 (3)	0.10640 (18)	0.0445 (5)
N3	0.24269 (11)	0.5509 (3)	0.1802 (3)	0.0683 (8)
O1	−0.12845 (9)	−0.0056 (3)	0.0043 (2)	0.0690 (7)
O2	−0.03632 (8)	0.1225 (2)	0.03858 (18)	0.0546 (5)
O3	0.11123 (10)	0.3162 (2)	0.0820 (2)	0.0604 (6)
Sn1	0.043848 (7)	0.17888 (2)	0.049245 (14)	0.04388 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.066 (3)	0.083 (3)	0.202 (6)	−0.031 (2)	0.060 (3)	−0.070 (3)
C2	0.0429 (16)	0.0581 (18)	0.0459 (16)	−0.0086 (14)	0.0129 (12)	−0.0022 (14)
C3	0.0378 (16)	0.072 (2)	0.0542 (19)	−0.0055 (14)	0.0135 (14)	0.0008 (15)
C4	0.0459 (18)	0.069 (2)	0.069 (2)	0.0046 (15)	0.0219 (16)	−0.0008 (16)
C5	0.0518 (18)	0.0535 (18)	0.0568 (19)	0.0003 (14)	0.0190 (14)	0.0026 (15)
C6	0.0419 (16)	0.0540 (17)	0.0397 (15)	−0.0042 (12)	0.0107 (12)	0.0063 (12)
C7	0.0394 (15)	0.0581 (18)	0.0354 (14)	−0.0030 (12)	0.0103 (11)	0.0039 (12)
C8	0.0472 (17)	0.0458 (15)	0.0459 (16)	−0.0028 (13)	0.0120 (12)	0.0027 (13)
C9	0.0451 (16)	0.0492 (16)	0.0418 (15)	−0.0110 (13)	0.0104 (12)	0.0012 (13)
C10	0.0479 (16)	0.0466 (16)	0.0421 (15)	−0.0124 (13)	0.0091 (12)	0.0037 (13)
C11	0.061 (2)	0.0536 (18)	0.061 (2)	−0.0123 (15)	0.0173 (16)	−0.0053 (15)
C12	0.082 (3)	0.0534 (19)	0.076 (3)	−0.023 (2)	0.022 (2)	−0.0120 (19)
C13	0.057 (2)	0.079 (3)	0.071 (3)	−0.0297 (18)	0.0076 (18)	−0.0001 (19)
C14	0.0514 (18)	0.0535 (18)	0.062 (2)	−0.0115 (15)	0.0101 (15)	−0.0008 (16)
C15	0.060 (2)	0.061 (2)	0.0445 (17)	−0.0025 (15)	0.0053 (14)	0.0008 (14)
C16	0.075 (2)	0.0510 (18)	0.0452 (18)	−0.0102 (16)	0.0203 (16)	−0.0036 (14)
N1	0.0450 (14)	0.0442 (13)	0.0535 (15)	−0.0077 (11)	0.0107 (11)	−0.0006 (11)
N2	0.0445 (14)	0.0462 (13)	0.0426 (13)	−0.0091 (11)	0.0100 (10)	−0.0005 (11)
N3	0.0507 (17)	0.0673 (19)	0.085 (2)	−0.0174 (14)	0.0116 (14)	−0.0038 (16)
O1	0.0457 (12)	0.0708 (15)	0.0958 (19)	−0.0155 (11)	0.0277 (12)	−0.0276 (14)
O2	0.0400 (11)	0.0565 (13)	0.0689 (15)	−0.0080 (10)	0.0162 (10)	−0.0079 (11)
O3	0.0509 (14)	0.0569 (14)	0.0793 (18)	−0.0155 (10)	0.0269 (12)	−0.0220 (11)
Sn1	0.04134 (14)	0.04977 (15)	0.04093 (14)	−0.01097 (8)	0.01049 (9)	−0.00053 (8)

Geometric parameters (Å, º) top

C1—O1	1.423 (4)	C10—C14	1.390 (4)
C1—H1A	0.9600	C11—C12	1.383 (5)
C1—H1B	0.9600	C11—H11	0.9300
C1—H1C	0.9600	C12—C13	1.374 (6)
C2—O1	1.367 (4)	C12—H12	0.9300
C2—C3	1.373 (5)	C13—N3	1.323 (5)
C2—C7	1.431 (4)	C13—H13	0.9300
C3—C4	1.397 (4)	C14—N3	1.332 (4)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.359 (5)	C15—Sn1	2.092 (3)
C4—H4	0.9300	C15—H15A	0.9600
C5—C6	1.405 (4)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C6—C7	1.406 (4)	C16—Sn1	2.098 (3)
C6—C8	1.430 (4)	C16—H16A	0.9600
C7—O2	1.327 (4)	C16—H16B	0.9600
C8—N2	1.287 (4)	C16—H16C	0.9600
C8—H8	0.9300	N1—N2	1.400 (3)
C9—O3	1.290 (3)	N2—Sn1	2.200 (3)
C9—N1	1.304 (4)	O2—Sn1	2.138 (2)
C9—C10	1.489 (4)	O3—Sn1	2.176 (2)
C10—C11	1.377 (4)

O1—C1—H1A	109.5	C11—C12—H12	120.8
O1—C1—H1B	109.5	N3—C13—C12	124.6 (3)
H1A—C1—H1B	109.5	N3—C13—H13	117.7
O1—C1—H1C	109.5	C12—C13—H13	117.7
H1A—C1—H1C	109.5	N3—C14—C10	124.5 (3)
H1B—C1—H1C	109.5	N3—C14—H14	117.7
O1—C2—C3	123.7 (3)	C10—C14—H14	117.7
O1—C2—C7	115.5 (3)	Sn1—C15—H15A	109.5
C3—C2—C7	120.8 (3)	Sn1—C15—H15B	109.5
C2—C3—C4	121.1 (3)	H15A—C15—H15B	109.5
C2—C3—H3	119.4	Sn1—C15—H15C	109.5
C4—C3—H3	119.4	H15A—C15—H15C	109.5
C5—C4—C3	119.3 (3)	H15B—C15—H15C	109.5
C5—C4—H4	120.4	Sn1—C16—H16A	109.5
C3—C4—H4	120.4	Sn1—C16—H16B	109.5
C4—C5—C6	121.2 (3)	H16A—C16—H16B	109.5
C4—C5—H5	119.4	Sn1—C16—H16C	109.5
C6—C5—H5	119.4	H16A—C16—H16C	109.5
C5—C6—C7	120.8 (3)	H16B—C16—H16C	109.5
C5—C6—C8	115.1 (3)	C9—N1—N2	110.7 (2)
C7—C6—C8	124.2 (3)	C8—N2—N1	114.8 (2)
O2—C7—C6	124.5 (3)	C8—N2—Sn1	128.1 (2)
O2—C7—C2	118.7 (3)	N1—N2—Sn1	117.03 (18)
C6—C7—C2	116.8 (3)	C13—N3—C14	116.1 (3)
N2—C8—C6	127.9 (3)	C2—O1—C1	116.2 (3)
N2—C8—H8	116.0	C7—O2—Sn1	131.74 (19)
C6—C8—H8	116.0	C9—O3—Sn1	114.66 (19)
O3—C9—N1	125.6 (3)	C15—Sn1—C16	146.08 (14)
O3—C9—C10	117.4 (3)	C15—Sn1—O2	95.11 (11)
N1—C9—C10	117.0 (3)	C16—Sn1—O2	94.66 (12)
C11—C10—C14	117.5 (3)	C15—Sn1—O3	92.46 (12)
C11—C10—C9	123.8 (3)	C16—Sn1—O3	92.19 (12)
C14—C10—C9	118.7 (3)	O2—Sn1—O3	155.02 (9)
C10—C11—C12	119.0 (4)	C15—Sn1—N2	106.13 (11)
C10—C11—H11	120.5	C16—Sn1—N2	107.23 (11)
C12—C11—H11	120.5	O2—Sn1—N2	83.30 (9)
C13—C12—C11	118.3 (4)	O3—Sn1—N2	71.73 (9)
C13—C12—H12	120.8

O1—C2—C3—C4	179.1 (3)	C6—C8—N2—N1	−179.5 (3)
C7—C2—C3—C4	−1.4 (5)	C6—C8—N2—Sn1	−0.4 (4)
C2—C3—C4—C5	0.2 (5)	C9—N1—N2—C8	−177.8 (3)
C3—C4—C5—C6	−0.3 (5)	C9—N1—N2—Sn1	3.0 (3)
C4—C5—C6—C7	1.5 (5)	C12—C13—N3—C14	−0.2 (6)
C4—C5—C6—C8	−178.7 (3)	C10—C14—N3—C13	−1.2 (5)
C5—C6—C7—O2	−179.7 (3)	C3—C2—O1—C1	−2.4 (5)
C8—C6—C7—O2	0.5 (5)	C7—C2—O1—C1	178.0 (4)
C5—C6—C7—C2	−2.5 (4)	C6—C7—O2—Sn1	−5.1 (4)
C8—C6—C7—C2	177.7 (3)	C2—C7—O2—Sn1	177.7 (2)
O1—C2—C7—O2	−0.5 (4)	N1—C9—O3—Sn1	−4.5 (4)
C3—C2—C7—O2	179.9 (3)	C10—C9—O3—Sn1	174.16 (19)
O1—C2—C7—C6	−177.9 (3)	C7—O2—Sn1—C15	110.8 (3)
C3—C2—C7—C6	2.4 (4)	C7—O2—Sn1—C16	−101.7 (3)
C5—C6—C8—N2	−177.5 (3)	C7—O2—Sn1—O3	3.7 (4)
C7—C6—C8—N2	2.3 (5)	C7—O2—Sn1—N2	5.1 (3)
O3—C9—C10—C11	177.3 (3)	C9—O3—Sn1—C15	−102.0 (2)
N1—C9—C10—C11	−3.9 (4)	C9—O3—Sn1—C16	111.6 (2)
O3—C9—C10—C14	−4.0 (4)	C9—O3—Sn1—O2	5.6 (4)
N1—C9—C10—C14	174.7 (3)	C9—O3—Sn1—N2	4.2 (2)
C14—C10—C11—C12	−0.1 (5)	C8—N2—Sn1—C15	−95.7 (3)
C9—C10—C11—C12	178.5 (3)	N1—N2—Sn1—C15	83.4 (2)
C10—C11—C12—C13	−1.1 (6)	C8—N2—Sn1—C16	90.5 (3)
C11—C12—C13—N3	1.3 (6)	N1—N2—Sn1—C16	−90.4 (2)
C11—C10—C14—N3	1.3 (5)	C8—N2—Sn1—O2	−2.3 (2)
C9—C10—C14—N3	−177.4 (3)	N1—N2—Sn1—O2	176.8 (2)
O3—C9—N1—N2	1.0 (4)	C8—N2—Sn1—O3	177.0 (3)
C10—C9—N1—N2	−177.6 (2)	N1—N2—Sn1—O3	−3.86 (19)

Experimental details

Crystal data
Chemical formula	[Sn(CH₃)₂(C₁₄H₁₁N₃O₃)]
M_r	418.02
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	26.121 (8), 9.795 (3), 13.227 (4)
β (°)	103.666 (4)
V (Å³)	3288.4 (17)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.57
Crystal size (mm)	0.35 × 0.16 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.609, 0.834
No. of measured, independent and observed [I > 2σ(I)] reflections	9367, 3574, 3115
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.087, 1.00
No. of reflections	3574
No. of parameters	211
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.54

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

C15—Sn1	2.092 (3)	O2—Sn1	2.138 (2)
C16—Sn1	2.098 (3)	O3—Sn1	2.176 (2)
N2—Sn1	2.200 (3)

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		CIF
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[N'-(3-Meth­oxy-2-oxidobenzyl­idene)nicotinohydrazidato]dimethyl­tin(IV)

Supporting information

Key indicators

checkCIF/PLATON results

[N'-(3-Methoxy-2-oxidobenzylidene)nicotinohydrazidato]dimethyltin(IV)