[N'-(5-Bromo-2-oxidobenzyl-idene-κO)-3-hydr-oxy-2-naphthohydrazidato-κN',O]dimethyl-tin(IV).

The Sn(IV) atom in the title compound, [Sn(CH(3))(2)(C(18)H(11)BrN(2)O(3))], shows a distorted cis-C(2)NO(2)Sn trigonal-bipyramidal coordination geometry, with an axial O-Sn-O angle of 155.27 (9)°. The presence of an intra-molecular O-H⋯N hydrogen bond between the amido N atom and hydr-oxy H atom in the Schiff base ligand helps to stabilize the overall mol-ecular structure.

Related literature

For related structures, see Lee et al. (2009a ▶,b ▶). For similar hydrazone dianions acting as O,N,O′-chelate ligands to tin in organotin compounds, see: Labib et al. (1996 ▶); Samanta et al. (2007 ▶).

Experimental

Crystal data

[Sn(CH3)2(C18H11BrN2O3)]

M = 531.96

Triclinic,

a = 6.8662 (5) Å

b = 11.7998 (9) Å

c = 11.9365 (9) Å

α = 87.464 (1)°

β = 76.128 (1)°

γ = 81.213 (1)°

V = 927.84 (12) Å3

Z = 2

Mo Kα radiation

μ = 3.55 mm−1

T = 145 K

0.39 × 0.37 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.338, T max = 0.740

5350 measured reflections

4028 independent reflections

3703 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.079

S = 1.14

4028 reflections

245 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.76 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶0); data reduction: SAINT; 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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810001133/sj2691sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001133/sj2691Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Sn(CH3)2(C18H11BrN2O3)]	Z = 2
Mr = 531.96	F(000) = 520
Triclinic, P1	Dx = 1.904 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8662 (5) Å	Cell parameters from 3900 reflections
b = 11.7998 (9) Å	θ = 2.5–30.6°
c = 11.9365 (9) Å	µ = 3.55 mm−1
α = 87.464 (1)°	T = 145 K
β = 76.128 (1)°	Plate, yellow
γ = 81.213 (1)°	0.39 × 0.37 × 0.09 mm
V = 927.84 (12) Å3

Bruker APEXII CCD area-detector diffractometer	4028 independent reflections
Radiation source: fine-focus sealed tube	3703 reflections with I > 2σ(I)
graphite	Rint = 0.016
ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.338, Tmax = 0.740	k = −10→15
5350 measured reflections	l = −15→15

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0316P)2 + 1.8608P] where P = (Fo2 + 2Fc2)/3
4028 reflections	(Δ/σ)max = 0.001
245 parameters	Δρmax = 0.63 e Å−3
1 restraint	Δρmin = −0.75 e Å−3

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.

	x	y	z	Uiso*/Ueq
Sn1	0.75049 (3)	0.561594 (19)	0.670242 (18)	0.01412 (8)
Br1	0.57215 (5)	−0.06224 (3)	0.64595 (3)	0.02011 (9)
N1	0.5307 (4)	0.4692 (2)	0.7889 (2)	0.0141 (5)
N2	0.3995 (4)	0.5332 (3)	0.8788 (2)	0.0172 (6)
O1	0.8546 (4)	0.4001 (2)	0.5966 (2)	0.0202 (5)
O2	0.5723 (4)	0.6809 (2)	0.7987 (2)	0.0228 (5)
O3	0.1095 (4)	0.5698 (2)	1.0656 (2)	0.0219 (5)
H3	0.1750	0.5344	1.0054	0.033*
C1	0.6138 (5)	0.2791 (3)	0.6996 (3)	0.0141 (6)
C2	0.7792 (5)	0.3027 (3)	0.6092 (3)	0.0152 (6)
C3	0.8681 (5)	0.2152 (3)	0.5277 (3)	0.0188 (7)
H3A	0.9776	0.2288	0.4655	0.023*
C4	0.7999 (5)	0.1105 (3)	0.5364 (3)	0.0158 (6)
H4	0.8593	0.0541	0.4790	0.019*
C5	0.6435 (5)	0.0871 (3)	0.6295 (3)	0.0164 (6)
C6	0.5524 (5)	0.1702 (3)	0.7093 (3)	0.0154 (6)
H6	0.4459	0.1540	0.7723	0.019*
C7	0.5032 (5)	0.3630 (3)	0.7853 (3)	0.0150 (6)
H7	0.3999	0.3379	0.8450	0.018*
C8	0.4332 (5)	0.6410 (3)	0.8761 (3)	0.0164 (6)
C9	0.3027 (5)	0.7184 (3)	0.9668 (3)	0.0151 (6)
C10	0.1483 (5)	0.6797 (3)	1.0581 (3)	0.0147 (6)
C11	0.0383 (5)	0.7555 (3)	1.1419 (3)	0.0154 (6)
H11	−0.0602	0.7291	1.2037	0.018*
C12	0.0673 (5)	0.8711 (3)	1.1392 (3)	0.0139 (6)
C13	−0.0460 (5)	0.9515 (3)	1.2244 (3)	0.0189 (7)
H13	−0.1429	0.9267	1.2880	0.023*
C14	−0.0175 (5)	1.0647 (3)	1.2160 (3)	0.0190 (7)
H14	−0.0962	1.1174	1.2732	0.023*
C15	0.1279 (5)	1.1033 (3)	1.1232 (3)	0.0192 (7)
H15	0.1469	1.1816	1.1186	0.023*
C16	0.2407 (5)	1.0289 (3)	1.0405 (3)	0.0164 (6)
H16	0.3376	1.0558	0.9782	0.020*
C17	0.2153 (5)	0.9112 (3)	1.0461 (3)	0.0138 (6)
C18	0.3312 (5)	0.8320 (3)	0.9627 (3)	0.0152 (6)
H18	0.4322	0.8573	0.9017	0.018*
C19	1.0295 (5)	0.5826 (3)	0.7067 (3)	0.0201 (7)
H19A	1.0478	0.5367	0.7748	0.030*
H19B	1.0291	0.6637	0.7216	0.030*
H19C	1.1409	0.5572	0.6405	0.030*
C20	0.6241 (5)	0.6376 (3)	0.5344 (3)	0.0227 (7)
H20A	0.4933	0.6117	0.5391	0.034*
H20B	0.7165	0.6150	0.4601	0.034*
H20C	0.6040	0.7213	0.5412	0.034*

	U11	U22	U33	U12	U13	U23
Sn1	0.01425 (12)	0.01281 (13)	0.01497 (12)	−0.00358 (8)	−0.00180 (8)	−0.00023 (8)
Br1	0.02169 (17)	0.01283 (18)	0.02579 (18)	−0.00506 (13)	−0.00342 (14)	−0.00316 (13)
N1	0.0149 (12)	0.0107 (13)	0.0174 (13)	−0.0042 (10)	−0.0034 (10)	0.0001 (10)
N2	0.0154 (13)	0.0220 (15)	0.0131 (12)	−0.0028 (11)	−0.0010 (10)	−0.0018 (11)
O1	0.0197 (12)	0.0140 (12)	0.0244 (12)	−0.0038 (9)	0.0011 (10)	−0.0017 (10)
O2	0.0216 (12)	0.0197 (13)	0.0232 (12)	−0.0073 (10)	0.0054 (10)	−0.0029 (10)
O3	0.0292 (13)	0.0127 (12)	0.0214 (12)	−0.0114 (10)	0.0050 (10)	−0.0056 (9)
C1	0.0160 (14)	0.0122 (15)	0.0151 (14)	−0.0024 (12)	−0.0058 (12)	−0.0001 (12)
C2	0.0162 (15)	0.0134 (16)	0.0172 (15)	−0.0026 (12)	−0.0061 (12)	0.0000 (12)
C3	0.0164 (15)	0.0223 (18)	0.0160 (15)	−0.0008 (13)	−0.0022 (12)	0.0031 (13)
C4	0.0175 (15)	0.0133 (16)	0.0168 (15)	−0.0006 (12)	−0.0051 (12)	−0.0014 (12)
C5	0.0173 (15)	0.0141 (16)	0.0194 (16)	−0.0024 (12)	−0.0075 (12)	−0.0002 (13)
C6	0.0146 (14)	0.0159 (16)	0.0171 (15)	−0.0062 (12)	−0.0042 (12)	0.0015 (12)
C7	0.0157 (14)	0.0140 (16)	0.0168 (15)	−0.0063 (12)	−0.0049 (12)	0.0033 (12)
C8	0.0131 (14)	0.0223 (18)	0.0143 (15)	−0.0037 (12)	−0.0040 (12)	0.0021 (13)
C9	0.0151 (14)	0.0150 (16)	0.0157 (15)	−0.0012 (12)	−0.0051 (12)	−0.0013 (12)
C10	0.0181 (15)	0.0119 (15)	0.0155 (15)	−0.0045 (12)	−0.0047 (12)	−0.0025 (12)
C11	0.0154 (14)	0.0174 (17)	0.0139 (14)	−0.0057 (12)	−0.0024 (12)	−0.0015 (12)
C12	0.0139 (14)	0.0144 (16)	0.0149 (14)	−0.0036 (12)	−0.0050 (11)	−0.0022 (12)
C13	0.0145 (15)	0.0284 (19)	0.0137 (15)	−0.0037 (13)	−0.0029 (12)	0.0001 (13)
C14	0.0202 (16)	0.0201 (18)	0.0178 (16)	−0.0024 (13)	−0.0059 (13)	−0.0044 (13)
C15	0.0207 (16)	0.0173 (17)	0.0206 (16)	−0.0011 (13)	−0.0073 (13)	−0.0035 (13)
C16	0.0182 (15)	0.0120 (16)	0.0202 (16)	−0.0047 (12)	−0.0051 (12)	−0.0025 (12)
C17	0.0162 (14)	0.0134 (15)	0.0125 (14)	−0.0016 (12)	−0.0049 (11)	−0.0024 (12)
C18	0.0147 (14)	0.0176 (17)	0.0132 (14)	−0.0020 (12)	−0.0035 (11)	−0.0007 (12)
C19	0.0173 (15)	0.0249 (19)	0.0193 (16)	−0.0090 (14)	−0.0031 (13)	−0.0007 (14)
C20	0.0225 (17)	0.0223 (19)	0.0238 (17)	−0.0015 (14)	−0.0079 (14)	0.0017 (14)

Sn1—O1	2.084 (2)	C8—C9	1.477 (5)
Sn1—C19	2.116 (3)	C9—C18	1.381 (5)
Sn1—C20	2.120 (3)	C9—C10	1.438 (4)
Sn1—O2	2.143 (2)	C10—C11	1.372 (5)
Sn1—N1	2.194 (3)	C11—C12	1.406 (5)
Br1—C5	1.890 (3)	C11—H11	0.9500
N1—C7	1.300 (4)	C12—C13	1.421 (5)
N1—N2	1.390 (4)	C12—C17	1.432 (4)
N2—C8	1.324 (5)	C13—C14	1.375 (5)
O1—C2	1.320 (4)	C13—H13	0.9500
O2—C8	1.290 (4)	C14—C15	1.412 (5)
O3—C10	1.358 (4)	C14—H14	0.9500
O3—H3	0.8400	C15—C16	1.360 (5)
C1—C6	1.404 (4)	C15—H15	0.9500
C1—C2	1.419 (4)	C16—C17	1.422 (5)
C1—C7	1.446 (5)	C16—H16	0.9500
C2—C3	1.413 (5)	C17—C18	1.405 (4)
C3—C4	1.377 (5)	C18—H18	0.9500
C3—H3A	0.9500	C19—H19A	0.9800
C4—C5	1.399 (5)	C19—H19B	0.9800
C4—H4	0.9500	C19—H19C	0.9800
C5—C6	1.367 (5)	C20—H20A	0.9800
C6—H6	0.9500	C20—H20B	0.9800
C7—H7	0.9500	C20—H20C	0.9800
O1—Sn1—C19	95.10 (12)	C18—C9—C8	118.2 (3)
O1—Sn1—C20	97.09 (13)	C10—C9—C8	122.5 (3)
C19—Sn1—C20	127.84 (14)	O3—C10—C11	118.6 (3)
O1—Sn1—O2	155.27 (9)	O3—C10—C9	122.3 (3)
C19—Sn1—O2	94.33 (12)	C11—C10—C9	119.2 (3)
C20—Sn1—O2	95.04 (13)	C10—C11—C12	121.9 (3)
O1—Sn1—N1	83.01 (10)	C10—C11—H11	119.0
C19—Sn1—N1	121.63 (12)	C12—C11—H11	119.0
C20—Sn1—N1	110.12 (12)	C11—C12—C13	123.0 (3)
O2—Sn1—N1	72.59 (10)	C11—C12—C17	119.2 (3)
C7—N1—N2	115.3 (3)	C13—C12—C17	117.8 (3)
C7—N1—Sn1	128.8 (2)	C14—C13—C12	121.0 (3)
N2—N1—Sn1	115.9 (2)	C14—C13—H13	119.5
C8—N2—N1	112.2 (3)	C12—C13—H13	119.5
C2—O1—Sn1	133.1 (2)	C13—C14—C15	120.6 (3)
C8—O2—Sn1	115.9 (2)	C13—C14—H14	119.7
C10—O3—H3	109.5	C15—C14—H14	119.7
C6—C1—C2	120.1 (3)	C16—C15—C14	120.3 (3)
C6—C1—C7	117.1 (3)	C16—C15—H15	119.9
C2—C1—C7	122.8 (3)	C14—C15—H15	119.9
O1—C2—C3	118.3 (3)	C15—C16—C17	120.7 (3)
O1—C2—C1	124.5 (3)	C15—C16—H16	119.6
C3—C2—C1	117.2 (3)	C17—C16—H16	119.6
C4—C3—C2	121.6 (3)	C18—C17—C16	122.1 (3)
C4—C3—H3A	119.2	C18—C17—C12	118.3 (3)
C2—C3—H3A	119.2	C16—C17—C12	119.6 (3)
C3—C4—C5	120.2 (3)	C9—C18—C17	121.9 (3)
C3—C4—H4	119.9	C9—C18—H18	119.0
C5—C4—H4	119.9	C17—C18—H18	119.0
C6—C5—C4	119.8 (3)	Sn1—C19—H19A	109.5
C6—C5—Br1	121.4 (2)	Sn1—C19—H19B	109.5
C4—C5—Br1	118.7 (3)	H19A—C19—H19B	109.5
C5—C6—C1	120.9 (3)	Sn1—C19—H19C	109.5
C5—C6—H6	119.5	H19A—C19—H19C	109.5
C1—C6—H6	119.5	H19B—C19—H19C	109.5
N1—C7—C1	126.6 (3)	Sn1—C20—H20A	109.5
N1—C7—H7	116.7	Sn1—C20—H20B	109.5
C1—C7—H7	116.7	H20A—C20—H20B	109.5
O2—C8—N2	123.4 (3)	Sn1—C20—H20C	109.5
O2—C8—C9	119.1 (3)	H20A—C20—H20C	109.5
N2—C8—C9	117.5 (3)	H20B—C20—H20C	109.5
C18—C9—C10	119.4 (3)
O1—Sn1—N1—C7	−5.4 (3)	Sn1—N1—C7—C1	−0.2 (5)
C19—Sn1—N1—C7	−97.1 (3)	C6—C1—C7—N1	−177.1 (3)
C20—Sn1—N1—C7	89.6 (3)	C2—C1—C7—N1	3.5 (5)
O2—Sn1—N1—C7	178.6 (3)	Sn1—O2—C8—N2	0.3 (4)
O1—Sn1—N1—N2	176.3 (2)	Sn1—O2—C8—C9	−179.4 (2)
C19—Sn1—N1—N2	84.6 (2)	N1—N2—C8—O2	0.0 (4)
C20—Sn1—N1—N2	−88.7 (2)	N1—N2—C8—C9	179.6 (3)
O2—Sn1—N1—N2	0.3 (2)	O2—C8—C9—C18	2.0 (4)
C7—N1—N2—C8	−178.8 (3)	N2—C8—C9—C18	−177.7 (3)
Sn1—N1—N2—C8	−0.3 (3)	O2—C8—C9—C10	−178.2 (3)
C19—Sn1—O1—C2	133.7 (3)	N2—C8—C9—C10	2.2 (5)
C20—Sn1—O1—C2	−97.1 (3)	C18—C9—C10—O3	178.5 (3)
O2—Sn1—O1—C2	21.7 (4)	C8—C9—C10—O3	−1.4 (5)
N1—Sn1—O1—C2	12.4 (3)	C18—C9—C10—C11	−2.7 (5)
O1—Sn1—O2—C8	−10.0 (4)	C8—C9—C10—C11	177.4 (3)
C19—Sn1—O2—C8	−122.1 (2)	O3—C10—C11—C12	−178.9 (3)
C20—Sn1—O2—C8	109.2 (2)	C9—C10—C11—C12	2.2 (5)
N1—Sn1—O2—C8	−0.3 (2)	C10—C11—C12—C13	179.4 (3)
Sn1—O1—C2—C3	166.5 (2)	C10—C11—C12—C17	0.2 (5)
Sn1—O1—C2—C1	−13.5 (5)	C11—C12—C13—C14	−177.7 (3)
C6—C1—C2—O1	−176.3 (3)	C17—C12—C13—C14	1.5 (5)
C7—C1—C2—O1	3.1 (5)	C12—C13—C14—C15	−1.0 (5)
C6—C1—C2—C3	3.7 (4)	C13—C14—C15—C16	0.4 (5)
C7—C1—C2—C3	−177.0 (3)	C14—C15—C16—C17	−0.3 (5)
O1—C2—C3—C4	178.9 (3)	C15—C16—C17—C18	−179.2 (3)
C1—C2—C3—C4	−1.1 (5)	C15—C16—C17—C12	0.9 (5)
C2—C3—C4—C5	−2.2 (5)	C11—C12—C17—C18	−2.1 (4)
C3—C4—C5—C6	2.8 (5)	C13—C12—C17—C18	178.7 (3)
C3—C4—C5—Br1	−174.0 (2)	C11—C12—C17—C16	177.8 (3)
C4—C5—C6—C1	−0.2 (5)	C13—C12—C17—C16	−1.4 (4)
Br1—C5—C6—C1	176.6 (2)	C10—C9—C18—C17	0.8 (5)
C2—C1—C6—C5	−3.1 (5)	C8—C9—C18—C17	−179.3 (3)
C7—C1—C6—C5	177.5 (3)	C16—C17—C18—C9	−178.3 (3)
N2—N1—C7—C1	178.1 (3)	C12—C17—C18—C9	1.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2	0.84	1.88	2.611 (4)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N2	0.84	1.88	2.611 (4)	144