{4-Hy­droxy-N′-[(2E,3Z)-4-oxido-4-phenyl­but-3-en-2-yl­idene]benzo­hydrazidato}dimethyl­tin(IV)

Affan, M.A.; Sam, N.B.; Ahmad, F.B.; White, F.; Tiekink, E.R.T.

doi:10.1107/S1600536811023506

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m965

doi:10.1107/S1600536811023506

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{4-Hydroxy-N′-[(2E,3Z)-4-oxido-4-phenylbut-3-en-2-ylidene]benzohydrazidato}dimethyltin(IV)

Md. Abu Affan,^a ‡ Norrihan B. Sam,^a Fasihuddin B. Ahmad,^a Fraser White ^b and Edward R. T. Tiekink ^c ^*

^aFaculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia, ^bAgilent Technologies UK Ltd, 10 Mead Road, Oxford Industrial Park, Oxford OX5 1QU, England, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 15 June 2011; accepted 16 June 2011; online 22 June 2011)

The Sn^IV atom in the title compound, [Sn(CH₃)₂(C₁₇H₁₄N₂O₃)], is five-coordinated within a C₂N₂O donor set provided by the N,N,O-tridentate ligand and two methyl groups. The resultant coordination geometry is intermediate between trigonal-bipyramidal and square-pyramidal. In the crystal, supramolecular zigzag chains propagating along the c- axis direction are mediated by O—H⋯O hydrogen bonds, and weak C—H⋯π interactions 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_r = 443.06
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.032
wR(F²) = 0.081
S = 1.00
3124 reflections
230 parameters
H-atom parameters constrained
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.72 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

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⋯Cg3^iv	0.95	2.89	3.668 (4)	140
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x, -y, -z+1; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811023506/hb5915sup1.cif

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

checkCIF report

Comment top

The title compound, (I), was examined in connection with on-going structural studies (Affan et al., 2010) of organotin derivatives of biological interest (Affan et al., 2009), and compliments the structure of the diphenyltin analogue (Affan et al., 2011).

The Sn atom in (I), Fig. 1, is five-coordinated by the tridentate ligand and two methyl groups, Table 1. The resulting C₂NO₂ donor set defines a coordination geometry intermediate between square pyramidal and trigonal bipyramidal geometry. This is quantified by the value of τ = 0.51 which compare to the τ values of 0.0 and 1.0 for ideal square pyramidal and trigonal bipyramidal geometries, respectively (Addison et al., 1984). For comparison, the values of τ for the two independent molecules in the structure of the diphenyltin analogue are 0.55 and 0.47 (Affan et al., 2011).

While the five-membered SnCN₂O chelate ring is almost planar with a r.m.s. deviation = 0.063 Å [max. deviations of 0.039 (1) and -0.052 (2) Å for the Sn and O1 atoms, respectively], there is considerable distortion in the SnC₃NO six-membered chelate [r.m.s. deviation = 0.226 Å] with the Sn and O3 atoms lying -0.209 (1) and 0.245 (3) Å out of the least-squares plane. Each of the benzene rings is twisted out of the plane from the adjacent chelate ring as seen in the O1—C1—C2—C3 and O3—C11—C12—C13 torsion angles of 13.7 (5) and -150.4 (4)°, respectively. The dihedral angle between the two benzene rings is 68.14 (18) °, indicating a twist in the tridentate ligand.

The crystal packing is dominated by O—H···O hydrogen bonding, Table 2, which leads to a zigzag supramolecular chain along the c axis, Fig. 2. These are consolidated in the crystal structure by C—H···π interactions, Table 2.

Related literature top

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 top

Benzoylacetone 4-hydroxybenzhydrazone (0.59 g, 2 mmol) was dissolved in distilled methanol (20 ml) under a nitrogen atmosphere. Potassium hydroxide (0.23 g, 4 mmol) dissolved in methanol (10 ml) was added drop wise to the solution. The colour of the solution changed from yellow to orange. The resulting mixture was refluxed for 1 h and then treated with dimethyltin dichloride (0.439 g, 2 mmol) in distilled methanol (10 ml). The resulting mixture was heated under reflux conditions for 4 h and allowed to cool to room temperature. Potassium chloride (KCl) was removed via filtration. The filtrate was evaporated to dryness using a rotary evaporator to yield yellow microcrystals. The microcrystals were filtered off and washed with ethanol and dried in vacuo over P₂O₅ overnight. Yellow blocks of (I) were obtained by slow evaporation of its acetone solution at room temperature. Yield: 0.94 g, 75%. M.pt.: 504–506 K. IR (ν_max, cm^-1, KBr): 3569 (OH), 1591 (C═N—N═C), 949 (N—N), 562 (Sn—C), 525 (Sn—O), 447 (Sn—N).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the supramolecular chain aligned along [001] in (I). The O—H···O hydrogen bonds are shown as orange dashed lines.
	Fig. 3. A view in projection down the c axis of the crystal packing in (I). The O—H···O hydrogen bonds and C—H···π interactions are shown as orange and purple dashed lines, respectively.

{4-Hydroxy-N-[(2E,3Z)-4-oxido-4-phenylbut-3-en-2- ylidene]benzohydrazidato}dimethyltin(IV) top

Crystal data top

[Sn(CH₃)₂(C₁₇H₁₄N₂O₃)]	F(000) = 888
M_r = 443.06	D_x = 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

Data collection top

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 monochromator	R_int = 0.038
ω scans	θ_max = 65.0°, θ_min = 4.5°
Absorption correction: analytical (CrysAlis PRO; Agilent, 2011)	h = −6→9
T_min = 0.696, T_max = 0.822	k = −24→24
5718 measured reflections	l = −13→13

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) = 0.081	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0384P)²] where P = (F_o² + 2F_c²)/3
3124 reflections	(Δ/σ)_max < 0.001
230 parameters	Δρ_max = 0.76 e Å⁻³
0 restraints	Δρ_min = −0.72 e Å⁻³

Crystal data top

[Sn(CH₃)₂(C₁₇H₁₄N₂O₃)]	V = 1850.58 (8) Å³
M_r = 443.06	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 8.0784 (2) Å	µ = 11.15 mm⁻¹
b = 20.5410 (5) Å	T = 150 K
c = 11.1678 (3) Å	0.22 × 0.16 × 0.10 mm
β = 93.025 (2)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3124 independent reflections
Absorption correction: analytical (CrysAlis PRO; Agilent, 2011)	2690 reflections with I > 2σ(I)
T_min = 0.696, T_max = 0.822	R_int = 0.038
5718 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.081	H-atom parameters constrained
S = 1.00	Δρ_max = 0.76 e Å⁻³
3124 reflections	Δρ_min = −0.72 e Å⁻³
230 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···Cg3^iv	0.95	2.89	3.668 (4)	140

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x, −y, −z+1; (iv) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Sn(CH₃)₂(C₁₇H₁₄N₂O₃)]
M_r	443.06
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	8.0784 (2), 20.5410 (5), 11.1678 (3)
β (°)	93.025 (2)
V (Å³)	1850.58 (8)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	11.15
Crystal size (mm)	0.22 × 0.16 × 0.10

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Analytical (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.696, 0.822
No. of measured, independent and observed [I > 2σ(I)] reflections	5718, 3124, 2690
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.588

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.081, 1.00
No. of reflections	3124
No. of parameters	230
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.72

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Selected geometric parameters (Å, º) top

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

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

Hydrogen-bond geometry (Å, º) top

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···Cg3^iv	0.95	2.89	3.668 (4)	140

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x, −y, −z+1; (iv) −x+1, y−1/2, −z+1/2.

Footnotes

‡Additional correspondence author, e-mail: maaffan@yahoo.com.

Acknowledgements

We thank MOSTI (grant No. 06–01-09-SF0046) and the Universiti Malaysia Sarawak for support of this work.

References

Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349–1356. CSD CrossRef Web of Science Google Scholar
Affan, M. A., Foo, S. W., Jusoh, I., Hanapi, S. & Tiekink, E. R. T. (2009). Inorg. Chim. Acta, 362, 5031–5037. Web of Science CSD CrossRef Google Scholar
Affan, M. A., Sam, N. B., Ahmad, F. B. & Tiekink, E. R. T. (2010). Acta Cryst. E66, m924. Web of Science CSD CrossRef IUCr Journals Google Scholar
Affan, M. A., Sam, N. B., Ahmad, F. B., White, F. & Tiekink, E. R. T. (2011). Acta Cryst. E67, m963–m964. Web of Science CSD CrossRef IUCr Journals Google Scholar
Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Oxford, UK. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 7| July 2011| Page m965

doi:10.1107/S1600536811023506

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

{4-Hy­dr­oxy-N′-[(2E,3Z)-4-oxido-4-phenyl­but-3-en-2-yl­­idene]benzo­hydrazidato}di­methyl­tin(IV)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

metal-organic compounds

{4-Hydroxy-N′-[(2E,3Z)-4-oxido-4-phenylbut-3-en-2-ylidene]benzohydrazidato}dimethyltin(IV)