{4-Hy-droxy-N'-[(2E,3Z)-4-oxido-4-phenyl-but-3-en-2-yl-idene]benzo-hydrazidato}dimethyl-tin(IV).

The Sn(IV) atom in the title compound, [Sn(CH(3))(2)(C(17)H(14)N(2)O(3))], is five-coordinated within a C(2)N(2)O donor set provided by the N,N,O-tridentate ligand and two methyl groups. The resultant coordination geometry is inter-mediate between trigonal-bipyramidal and square-pyramidal. In the crystal, supra-molecular zigzag chains propagating along the c- axis direction are mediated by O-H⋯O hydrogen bonds, and weak C-H⋯π inter-actions consolidate the packing.

Related literature

For background to the biological inter­est of related compounds, see: Affan et al. (2010 ▶). For related structures, see: Affan et al. (2009 ▶, 2011 ▶). For additional structural analysis, see: Addison et al. (1984 ▶).

Experimental

Crystal data

[Sn(CH3)2(C17H14N2O3)]

M = 443.06

Monoclinic,

a = 8.0784 (2) Å

b = 20.5410 (5) Å

c = 11.1678 (3) Å

β = 93.025 (2)°

V = 1850.58 (8) Å3

Z = 4

Cu Kα radiation

μ = 11.15 mm−1

T = 150 K

0.22 × 0.16 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: analytical (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.696, T max = 0.822

5718 measured reflections

3124 independent reflections

2690 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.081

S = 1.00

3124 reflections

230 parameters

H-atom parameters constrained

Δρmax = 0.76 e Å−3

Δρmin = −0.72 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811023506/hb5915sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023506/hb5915Isup2.hkl

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

[Sn(CH3)2(C17H14N2O3)]	F(000) = 888
Mr = 443.06	Dx = 1.590 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 3495 reflections
a = 8.0784 (2) Å	θ = 4.0–74.2°
b = 20.5410 (5) Å	µ = 11.15 mm−1
c = 11.1678 (3) Å	T = 150 K
β = 93.025 (2)°	Block, yellow
V = 1850.58 (8) Å3	0.22 × 0.16 × 0.10 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	3124 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2690 reflections with I > 2σ(I)
Mirror	Rint = 0.038
ω scans	θmax = 65.0°, θmin = 4.5°
Absorption correction: analytical (CrysAlis PRO; Agilent, 2011)	h = −6→9
Tmin = 0.696, Tmax = 0.822	k = −24→24
5718 measured reflections	l = −13→13

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) = 0.081	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0384P)2] where P = (Fo2 + 2Fc2)/3
3124 reflections	(Δ/σ)max < 0.001
230 parameters	Δρmax = 0.76 e Å−3
0 restraints	Δρmin = −0.72 e Å−3

Experimental. Agilent Technologies (2011) CrysAlis PRO Software system, version 1.171.34.49, Agilent Technologies UK Ltd, Oxford, UK

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Sn	0.18670 (3)	0.011355 (13)	0.22279 (2)	0.02375 (11)
O1	0.0690 (3)	0.09638 (13)	0.2930 (2)	0.0267 (6)
O2	−0.0780 (3)	0.34947 (13)	0.5942 (2)	0.0309 (6)
H2o	−0.0354	0.3553	0.6636	0.046*
O3	0.3618 (3)	−0.06412 (14)	0.2237 (2)	0.0333 (7)
N1	0.1880 (4)	0.06513 (16)	0.4764 (3)	0.0242 (7)
N2	0.2394 (4)	0.01068 (16)	0.4134 (3)	0.0232 (7)
C1	0.1054 (4)	0.10630 (19)	0.4079 (3)	0.0230 (8)
C2	0.0519 (4)	0.16830 (19)	0.4610 (3)	0.0208 (8)
C3	−0.0628 (5)	0.2084 (2)	0.3999 (3)	0.0263 (9)
H3	−0.1131	0.1942	0.3256	0.032*
C4	−0.1051 (5)	0.2685 (2)	0.4452 (3)	0.0275 (9)
H4	−0.1835	0.2952	0.4020	0.033*
C5	−0.0331 (5)	0.28957 (19)	0.5535 (3)	0.0240 (8)
C6	0.0800 (4)	0.2492 (2)	0.6178 (3)	0.0250 (8)
H6	0.1282	0.2631	0.6929	0.030*
C7	0.1213 (4)	0.18929 (19)	0.5719 (3)	0.0245 (8)
H7	0.1975	0.1621	0.6159	0.029*
C8	0.2979 (5)	−0.0386 (2)	0.4775 (3)	0.0247 (8)
C9	0.3027 (5)	−0.0339 (2)	0.6122 (3)	0.0311 (9)
H9A	0.3736	0.0027	0.6385	0.047*
H9B	0.3474	−0.0744	0.6472	0.047*
H9C	0.1903	−0.0269	0.6385	0.047*
C10	0.3544 (5)	−0.0971 (2)	0.4265 (3)	0.0268 (9)
H10	0.3750	−0.1326	0.4797	0.032*
C11	0.3827 (5)	−0.1079 (2)	0.3075 (3)	0.0255 (9)
C12	0.4463 (4)	−0.1711 (2)	0.2669 (3)	0.0243 (8)
C13	0.4076 (5)	−0.2292 (2)	0.3228 (4)	0.0286 (9)
H13	0.3440	−0.2285	0.3919	0.034*
C14	0.4607 (5)	−0.2880 (2)	0.2787 (4)	0.0340 (10)
H14	0.4317	−0.3274	0.3169	0.041*
C15	0.5565 (5)	−0.2900 (2)	0.1787 (4)	0.0365 (10)
H15	0.5938	−0.3304	0.1489	0.044*
C16	0.5966 (5)	−0.2323 (2)	0.1232 (4)	0.0351 (10)
H16	0.6629	−0.2332	0.0554	0.042*
C17	0.5410 (5)	−0.1731 (2)	0.1658 (4)	0.0295 (9)
H17	0.5674	−0.1339	0.1260	0.035*
C18	0.3273 (6)	0.0647 (2)	0.1034 (4)	0.0379 (11)
H18A	0.4406	0.0701	0.1380	0.057*
H18B	0.2767	0.1076	0.0896	0.057*
H18C	0.3302	0.0413	0.0271	0.057*
C19	−0.0261 (6)	−0.0439 (2)	0.1720 (4)	0.0451 (12)
H19A	−0.0003	−0.0739	0.1074	0.068*
H19B	−0.1158	−0.0146	0.1439	0.068*
H19C	−0.0611	−0.0688	0.2411	0.068*

	U11	U22	U33	U12	U13	U23
Sn	0.02822 (16)	0.02438 (17)	0.01860 (15)	0.00018 (11)	0.00060 (10)	−0.00033 (10)
O1	0.0341 (15)	0.0238 (15)	0.0217 (14)	0.0056 (12)	−0.0027 (10)	−0.0038 (11)
O2	0.0410 (17)	0.0274 (16)	0.0237 (15)	0.0055 (13)	−0.0045 (12)	−0.0050 (12)
O3	0.0419 (17)	0.0311 (16)	0.0277 (15)	0.0123 (14)	0.0084 (12)	0.0059 (13)
N1	0.0271 (17)	0.0232 (18)	0.0222 (16)	0.0013 (14)	0.0008 (13)	−0.0027 (14)
N2	0.0250 (16)	0.0260 (18)	0.0192 (16)	0.0003 (14)	0.0042 (13)	0.0003 (14)
C1	0.0199 (18)	0.029 (2)	0.0200 (19)	−0.0050 (16)	0.0023 (14)	0.0008 (17)
C2	0.0194 (18)	0.024 (2)	0.0195 (18)	−0.0024 (16)	0.0012 (14)	0.0012 (15)
C3	0.025 (2)	0.033 (2)	0.0200 (19)	−0.0033 (18)	−0.0027 (15)	−0.0012 (17)
C4	0.029 (2)	0.029 (2)	0.0241 (19)	0.0065 (18)	−0.0018 (15)	−0.0001 (17)
C5	0.026 (2)	0.025 (2)	0.0218 (19)	−0.0037 (17)	0.0009 (14)	−0.0006 (16)
C6	0.025 (2)	0.029 (2)	0.0204 (18)	−0.0059 (17)	−0.0005 (15)	−0.0040 (17)
C7	0.0220 (19)	0.028 (2)	0.0238 (19)	−0.0009 (17)	−0.0001 (14)	0.0034 (17)
C8	0.0236 (19)	0.029 (2)	0.0211 (19)	−0.0008 (18)	0.0019 (14)	0.0010 (17)
C9	0.044 (2)	0.029 (2)	0.020 (2)	0.002 (2)	0.0029 (17)	−0.0001 (18)
C10	0.030 (2)	0.027 (2)	0.0237 (19)	0.0031 (18)	0.0024 (15)	0.0033 (17)
C11	0.0230 (19)	0.027 (2)	0.026 (2)	−0.0023 (17)	0.0008 (15)	−0.0008 (17)
C12	0.0177 (18)	0.028 (2)	0.027 (2)	0.0000 (16)	−0.0033 (14)	−0.0035 (17)
C13	0.023 (2)	0.032 (2)	0.031 (2)	−0.0025 (18)	0.0005 (16)	−0.0011 (18)
C14	0.027 (2)	0.027 (2)	0.047 (3)	−0.0004 (19)	−0.0059 (18)	−0.001 (2)
C15	0.031 (2)	0.036 (3)	0.041 (3)	0.009 (2)	−0.0062 (18)	−0.011 (2)
C16	0.028 (2)	0.046 (3)	0.031 (2)	0.008 (2)	0.0005 (17)	−0.004 (2)
C17	0.026 (2)	0.034 (2)	0.028 (2)	0.0020 (19)	0.0032 (15)	0.0007 (19)
C18	0.043 (3)	0.040 (3)	0.031 (2)	−0.008 (2)	0.0029 (18)	0.003 (2)
C19	0.045 (3)	0.042 (3)	0.048 (3)	−0.011 (2)	0.006 (2)	−0.020 (2)

Sn—O1	2.156 (3)	C8—C9	1.506 (5)
Sn—O3	2.099 (3)	C9—H9A	0.9800
Sn—N2	2.148 (3)	C9—H9B	0.9800
Sn—C18	2.105 (4)	C9—H9C	0.9800
Sn—C19	2.112 (4)	C10—C11	1.377 (5)
O1—C1	1.317 (4)	C10—H10	0.9500
O2—C5	1.367 (5)	C11—C12	1.476 (5)
O2—H2O	0.8400	C12—C13	1.390 (6)
O3—C11	1.303 (5)	C12—C17	1.398 (5)
N1—C1	1.300 (5)	C13—C14	1.380 (6)
N1—N2	1.396 (4)	C13—H13	0.9500
N2—C8	1.313 (5)	C14—C15	1.393 (6)
C1—C2	1.479 (5)	C14—H14	0.9500
C2—C3	1.391 (5)	C15—C16	1.384 (6)
C2—C7	1.400 (5)	C15—H15	0.9500
C3—C4	1.384 (6)	C16—C17	1.388 (6)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.383 (5)	C17—H17	0.9500
C4—H4	0.9500	C18—H18A	0.9800
C5—C6	1.404 (5)	C18—H18B	0.9800
C6—C7	1.381 (5)	C18—H18C	0.9800
C6—H6	0.9500	C19—H19A	0.9800
C7—H7	0.9500	C19—H19B	0.9800
C8—C10	1.417 (5)	C19—H19C	0.9800
O3—Sn—C18	90.09 (15)	C8—C9—H9B	109.5
O3—Sn—C19	98.26 (16)	H9A—C9—H9B	109.5
O1—Sn—O3	155.08 (10)	C8—C9—H9C	109.5
C18—Sn—C19	124.65 (18)	H9A—C9—H9C	109.5
O3—Sn—N2	83.82 (11)	H9B—C9—H9C	109.5
C18—Sn—N2	123.05 (15)	C11—C10—C8	126.7 (4)
C19—Sn—N2	112.24 (16)	C11—C10—H10	116.7
C18—Sn—O1	94.10 (15)	C8—C10—H10	116.7
C19—Sn—O1	99.46 (15)	O3—C11—C10	124.1 (4)
N2—Sn—O1	73.31 (11)	O3—C11—C12	114.8 (3)
C1—O1—Sn	113.6 (2)	C10—C11—C12	121.0 (4)
C5—O2—H2O	109.5	C13—C12—C17	118.8 (4)
C11—O3—Sn	125.1 (2)	C13—C12—C11	121.8 (3)
C1—N1—N2	112.4 (3)	C17—C12—C11	119.3 (4)
C8—N2—N1	116.8 (3)	C14—C13—C12	120.7 (4)
C8—N2—Sn	126.3 (3)	C14—C13—H13	119.7
N1—N2—Sn	116.5 (2)	C12—C13—H13	119.7
N1—C1—O1	123.6 (4)	C13—C14—C15	120.5 (4)
N1—C1—C2	118.4 (3)	C13—C14—H14	119.7
O1—C1—C2	118.0 (3)	C15—C14—H14	119.7
C3—C2—C7	118.5 (4)	C16—C15—C14	119.1 (4)
C3—C2—C1	121.0 (3)	C16—C15—H15	120.4
C7—C2—C1	120.5 (3)	C14—C15—H15	120.4
C4—C3—C2	121.3 (4)	C15—C16—C17	120.6 (4)
C4—C3—H3	119.3	C15—C16—H16	119.7
C2—C3—H3	119.3	C17—C16—H16	119.7
C5—C4—C3	119.9 (4)	C16—C17—C12	120.3 (4)
C5—C4—H4	120.1	C16—C17—H17	119.9
C3—C4—H4	120.1	C12—C17—H17	119.9
O2—C5—C4	117.8 (3)	Sn—C18—H18A	109.5
O2—C5—C6	122.6 (3)	Sn—C18—H18B	109.5
C4—C5—C6	119.6 (4)	H18A—C18—H18B	109.5
C7—C6—C5	120.0 (3)	Sn—C18—H18C	109.5
C7—C6—H6	120.0	H18A—C18—H18C	109.5
C5—C6—H6	120.0	H18B—C18—H18C	109.5
C6—C7—C2	120.7 (4)	Sn—C19—H19A	109.5
C6—C7—H7	119.7	Sn—C19—H19B	109.5
C2—C7—H7	119.7	H19A—C19—H19B	109.5
N2—C8—C10	123.3 (3)	Sn—C19—H19C	109.5
N2—C8—C9	119.0 (4)	H19A—C19—H19C	109.5
C10—C8—C9	117.7 (4)	H19B—C19—H19C	109.5
C8—C9—H9A	109.5
O3—Sn—O1—C1	−17.4 (4)	C3—C4—C5—O2	179.6 (3)
C18—Sn—O1—C1	−116.5 (3)	C3—C4—C5—C6	−1.3 (6)
C19—Sn—O1—C1	117.4 (3)	O2—C5—C6—C7	−179.7 (3)
N2—Sn—O1—C1	6.8 (2)	C4—C5—C6—C7	1.2 (6)
C18—Sn—O3—C11	158.3 (3)	C5—C6—C7—C2	0.3 (6)
C19—Sn—O3—C11	−76.6 (3)	C3—C2—C7—C6	−1.7 (5)
N2—Sn—O3—C11	35.0 (3)	C1—C2—C7—C6	175.6 (3)
O1—Sn—O3—C11	58.3 (4)	N1—N2—C8—C10	179.9 (3)
C1—N1—N2—C8	−168.5 (3)	Sn—N2—C8—C10	8.0 (5)
C1—N1—N2—Sn	4.2 (4)	N1—N2—C8—C9	1.2 (5)
O3—Sn—N2—C8	−24.1 (3)	Sn—N2—C8—C9	−170.7 (3)
C18—Sn—N2—C8	−110.2 (3)	N2—C8—C10—C11	11.3 (6)
C19—Sn—N2—C8	72.3 (3)	C9—C8—C10—C11	−170.0 (4)
O1—Sn—N2—C8	165.9 (3)	Sn—O3—C11—C10	−30.7 (5)
O3—Sn—N2—N1	164.0 (3)	Sn—O3—C11—C12	151.4 (3)
C18—Sn—N2—N1	78.0 (3)	C8—C10—C11—O3	0.6 (6)
C19—Sn—N2—N1	−99.5 (3)	C8—C10—C11—C12	178.3 (4)
O1—Sn—N2—N1	−5.9 (2)	O3—C11—C12—C13	−150.4 (4)
N2—N1—C1—O1	2.4 (5)	C10—C11—C12—C13	31.7 (5)
N2—N1—C1—C2	−176.3 (3)	O3—C11—C12—C17	26.3 (5)
Sn—O1—C1—N1	−7.7 (5)	C10—C11—C12—C17	−151.6 (4)
Sn—O1—C1—C2	171.1 (2)	C17—C12—C13—C14	−0.5 (6)
N1—C1—C2—C3	−167.5 (3)	C11—C12—C13—C14	176.2 (4)
O1—C1—C2—C3	13.7 (5)	C12—C13—C14—C15	1.1 (6)
N1—C1—C2—C7	15.3 (5)	C13—C14—C15—C16	−0.6 (6)
O1—C1—C2—C7	−163.5 (3)	C14—C15—C16—C17	−0.6 (6)
C7—C2—C3—C4	1.7 (6)	C15—C16—C17—C12	1.3 (6)
C1—C2—C3—C4	−175.6 (3)	C13—C12—C17—C16	−0.7 (6)
C2—C3—C4—C5	−0.2 (6)	C11—C12—C17—C16	−177.5 (4)

Cg1, Cg2 and Cg3 are the centroids of the C12–C17, Sn,O1,C1,N1,N2 and C2–C7 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2o···O1i	0.84	1.91	2.702 (3)	156
C4—H4···Cg1ii	0.95	2.91	3.624 (4)	133
C9—H9c···Cg2iii	0.98	2.88	3.777 (4)	152
C16—H16···Cg3iv	0.95	2.89	3.668 (4)	140

Sn—O1	2.156 (3)
Sn—O3	2.099 (3)
Sn—N2	2.148 (3)
Sn—C18	2.105 (4)
Sn—C19	2.112 (4)

O1—Sn—O3	155.08 (10)
C18—Sn—C19	124.65 (18)

Table 2

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C12–C17, Sn,O1,C1,N1,N2 and C2–C7 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2o⋯O1i	0.84	1.91	2.702 (3)	156
C4—H4⋯Cg1ii	0.95	2.91	3.624 (4)	133
C9—H9c⋯Cg2iii	0.98	2.88	3.777 (4)	152
C16—H16⋯Cg3iv	0.95	2.89	3.668 (4)	140

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .