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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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 SnIV 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[Affan, M. A., Sam, N. B., Ahmad, F. B. & Tiekink, E. R. T. (2010). Acta Cryst. E66, m924.]). For related structures, see: Affan et al. (2009[Affan, M. A., Foo, S. W., Jusoh, I., Hanapi, S. & Tiekink, E. R. T. (2009). Inorg. Chim. Acta, 362, 5031-5037.], 2011[Affan, M. A., Sam, N. B., Ahmad, F. B., White, F. & Tiekink, E. R. T. (2011). Acta Cryst. E67, m963-m964.]). For additional structural analysis, see: Addison et al. (1984[Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349-1356.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(CH3)2(C17H14N2O3)]

  • Mr = 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[Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Oxford, UK.]) Tmin = 0.696, Tmax = 0.822

  • 5718 measured reflections

  • 3124 independent reflections

  • 2690 reflections with I > 2σ(I)

  • Rint = 0.038

Refinement
  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 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

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 DA 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) [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[Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Oxford, UK.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


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 (νmax, cm-1, KBr): 3569 (OH), 1591 (CN—NC), 949 (N—N), 562 (Sn—C), 525 (Sn—O), 447 (Sn—N).

Refinement top

Carbon-bound H-atoms were placed in calculated positions (O—H = 0.84 Å; C—H = 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation with Uiso(H) set to 1.2-Ueq(C) and 1.5-Ueq(O, methyl-C).

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
[Figure 1] Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 50% probability level.
[Figure 2] 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.
[Figure 3] 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
Mr = 443.06Dx = 1.590 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybcCell parameters from 3495 reflections
a = 8.0784 (2) Åθ = 4.0–74.2°
b = 20.5410 (5) ŵ = 11.15 mm1
c = 11.1678 (3) ÅT = 150 K
β = 93.025 (2)°Block, yellow
V = 1850.58 (8) Å30.22 × 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 Source2690 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.038
ω scansθmax = 65.0°, θmin = 4.5°
Absorption correction: analytical
(CrysAlis PRO; Agilent, 2011)
h = 69
Tmin = 0.696, Tmax = 0.822k = 2424
5718 measured reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081H-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 parametersΔρmax = 0.76 e Å3
0 restraintsΔρmin = 0.72 e Å3
Crystal data top
[Sn(CH3)2(C17H14N2O3)]V = 1850.58 (8) Å3
Mr = 443.06Z = 4
Monoclinic, P21/cCu Kα radiation
a = 8.0784 (2) ŵ = 11.15 mm1
b = 20.5410 (5) ÅT = 150 K
c = 11.1678 (3) Å0.22 × 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)
Tmin = 0.696, Tmax = 0.822Rint = 0.038
5718 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.081H-atom parameters constrained
S = 1.00Δρmax = 0.76 e Å3
3124 reflectionsΔρmin = 0.72 e Å3
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
xyzUiso*/Ueq
Sn0.18670 (3)0.011355 (13)0.22279 (2)0.02375 (11)
O10.0690 (3)0.09638 (13)0.2930 (2)0.0267 (6)
O20.0780 (3)0.34947 (13)0.5942 (2)0.0309 (6)
H2o0.03540.35530.66360.046*
O30.3618 (3)0.06412 (14)0.2237 (2)0.0333 (7)
N10.1880 (4)0.06513 (16)0.4764 (3)0.0242 (7)
N20.2394 (4)0.01068 (16)0.4134 (3)0.0232 (7)
C10.1054 (4)0.10630 (19)0.4079 (3)0.0230 (8)
C20.0519 (4)0.16830 (19)0.4610 (3)0.0208 (8)
C30.0628 (5)0.2084 (2)0.3999 (3)0.0263 (9)
H30.11310.19420.32560.032*
C40.1051 (5)0.2685 (2)0.4452 (3)0.0275 (9)
H40.18350.29520.40200.033*
C50.0331 (5)0.28957 (19)0.5535 (3)0.0240 (8)
C60.0800 (4)0.2492 (2)0.6178 (3)0.0250 (8)
H60.12820.26310.69290.030*
C70.1213 (4)0.18929 (19)0.5719 (3)0.0245 (8)
H70.19750.16210.61590.029*
C80.2979 (5)0.0386 (2)0.4775 (3)0.0247 (8)
C90.3027 (5)0.0339 (2)0.6122 (3)0.0311 (9)
H9A0.37360.00270.63850.047*
H9B0.34740.07440.64720.047*
H9C0.19030.02690.63850.047*
C100.3544 (5)0.0971 (2)0.4265 (3)0.0268 (9)
H100.37500.13260.47970.032*
C110.3827 (5)0.1079 (2)0.3075 (3)0.0255 (9)
C120.4463 (4)0.1711 (2)0.2669 (3)0.0243 (8)
C130.4076 (5)0.2292 (2)0.3228 (4)0.0286 (9)
H130.34400.22850.39190.034*
C140.4607 (5)0.2880 (2)0.2787 (4)0.0340 (10)
H140.43170.32740.31690.041*
C150.5565 (5)0.2900 (2)0.1787 (4)0.0365 (10)
H150.59380.33040.14890.044*
C160.5966 (5)0.2323 (2)0.1232 (4)0.0351 (10)
H160.66290.23320.05540.042*
C170.5410 (5)0.1731 (2)0.1658 (4)0.0295 (9)
H170.56740.13390.12600.035*
C180.3273 (6)0.0647 (2)0.1034 (4)0.0379 (11)
H18A0.44060.07010.13800.057*
H18B0.27670.10760.08960.057*
H18C0.33020.04130.02710.057*
C190.0261 (6)0.0439 (2)0.1720 (4)0.0451 (12)
H19A0.00030.07390.10740.068*
H19B0.11580.01460.14390.068*
H19C0.06110.06880.24110.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn0.02822 (16)0.02438 (17)0.01860 (15)0.00018 (11)0.00060 (10)0.00033 (10)
O10.0341 (15)0.0238 (15)0.0217 (14)0.0056 (12)0.0027 (10)0.0038 (11)
O20.0410 (17)0.0274 (16)0.0237 (15)0.0055 (13)0.0045 (12)0.0050 (12)
O30.0419 (17)0.0311 (16)0.0277 (15)0.0123 (14)0.0084 (12)0.0059 (13)
N10.0271 (17)0.0232 (18)0.0222 (16)0.0013 (14)0.0008 (13)0.0027 (14)
N20.0250 (16)0.0260 (18)0.0192 (16)0.0003 (14)0.0042 (13)0.0003 (14)
C10.0199 (18)0.029 (2)0.0200 (19)0.0050 (16)0.0023 (14)0.0008 (17)
C20.0194 (18)0.024 (2)0.0195 (18)0.0024 (16)0.0012 (14)0.0012 (15)
C30.025 (2)0.033 (2)0.0200 (19)0.0033 (18)0.0027 (15)0.0012 (17)
C40.029 (2)0.029 (2)0.0241 (19)0.0065 (18)0.0018 (15)0.0001 (17)
C50.026 (2)0.025 (2)0.0218 (19)0.0037 (17)0.0009 (14)0.0006 (16)
C60.025 (2)0.029 (2)0.0204 (18)0.0059 (17)0.0005 (15)0.0040 (17)
C70.0220 (19)0.028 (2)0.0238 (19)0.0009 (17)0.0001 (14)0.0034 (17)
C80.0236 (19)0.029 (2)0.0211 (19)0.0008 (18)0.0019 (14)0.0010 (17)
C90.044 (2)0.029 (2)0.020 (2)0.002 (2)0.0029 (17)0.0001 (18)
C100.030 (2)0.027 (2)0.0237 (19)0.0031 (18)0.0024 (15)0.0033 (17)
C110.0230 (19)0.027 (2)0.026 (2)0.0023 (17)0.0008 (15)0.0008 (17)
C120.0177 (18)0.028 (2)0.027 (2)0.0000 (16)0.0033 (14)0.0035 (17)
C130.023 (2)0.032 (2)0.031 (2)0.0025 (18)0.0005 (16)0.0011 (18)
C140.027 (2)0.027 (2)0.047 (3)0.0004 (19)0.0059 (18)0.001 (2)
C150.031 (2)0.036 (3)0.041 (3)0.009 (2)0.0062 (18)0.011 (2)
C160.028 (2)0.046 (3)0.031 (2)0.008 (2)0.0005 (17)0.004 (2)
C170.026 (2)0.034 (2)0.028 (2)0.0020 (19)0.0032 (15)0.0007 (19)
C180.043 (3)0.040 (3)0.031 (2)0.008 (2)0.0029 (18)0.003 (2)
C190.045 (3)0.042 (3)0.048 (3)0.011 (2)0.006 (2)0.020 (2)
Geometric parameters (Å, º) top
Sn—O12.156 (3)C8—C91.506 (5)
Sn—O32.099 (3)C9—H9A0.9800
Sn—N22.148 (3)C9—H9B0.9800
Sn—C182.105 (4)C9—H9C0.9800
Sn—C192.112 (4)C10—C111.377 (5)
O1—C11.317 (4)C10—H100.9500
O2—C51.367 (5)C11—C121.476 (5)
O2—H2O0.8400C12—C131.390 (6)
O3—C111.303 (5)C12—C171.398 (5)
N1—C11.300 (5)C13—C141.380 (6)
N1—N21.396 (4)C13—H130.9500
N2—C81.313 (5)C14—C151.393 (6)
C1—C21.479 (5)C14—H140.9500
C2—C31.391 (5)C15—C161.384 (6)
C2—C71.400 (5)C15—H150.9500
C3—C41.384 (6)C16—C171.388 (6)
C3—H30.9500C16—H160.9500
C4—C51.383 (5)C17—H170.9500
C4—H40.9500C18—H18A0.9800
C5—C61.404 (5)C18—H18B0.9800
C6—C71.381 (5)C18—H18C0.9800
C6—H60.9500C19—H19A0.9800
C7—H70.9500C19—H19B0.9800
C8—C101.417 (5)C19—H19C0.9800
O3—Sn—C1890.09 (15)C8—C9—H9B109.5
O3—Sn—C1998.26 (16)H9A—C9—H9B109.5
O1—Sn—O3155.08 (10)C8—C9—H9C109.5
C18—Sn—C19124.65 (18)H9A—C9—H9C109.5
O3—Sn—N283.82 (11)H9B—C9—H9C109.5
C18—Sn—N2123.05 (15)C11—C10—C8126.7 (4)
C19—Sn—N2112.24 (16)C11—C10—H10116.7
C18—Sn—O194.10 (15)C8—C10—H10116.7
C19—Sn—O199.46 (15)O3—C11—C10124.1 (4)
N2—Sn—O173.31 (11)O3—C11—C12114.8 (3)
C1—O1—Sn113.6 (2)C10—C11—C12121.0 (4)
C5—O2—H2O109.5C13—C12—C17118.8 (4)
C11—O3—Sn125.1 (2)C13—C12—C11121.8 (3)
C1—N1—N2112.4 (3)C17—C12—C11119.3 (4)
C8—N2—N1116.8 (3)C14—C13—C12120.7 (4)
C8—N2—Sn126.3 (3)C14—C13—H13119.7
N1—N2—Sn116.5 (2)C12—C13—H13119.7
N1—C1—O1123.6 (4)C13—C14—C15120.5 (4)
N1—C1—C2118.4 (3)C13—C14—H14119.7
O1—C1—C2118.0 (3)C15—C14—H14119.7
C3—C2—C7118.5 (4)C16—C15—C14119.1 (4)
C3—C2—C1121.0 (3)C16—C15—H15120.4
C7—C2—C1120.5 (3)C14—C15—H15120.4
C4—C3—C2121.3 (4)C15—C16—C17120.6 (4)
C4—C3—H3119.3C15—C16—H16119.7
C2—C3—H3119.3C17—C16—H16119.7
C5—C4—C3119.9 (4)C16—C17—C12120.3 (4)
C5—C4—H4120.1C16—C17—H17119.9
C3—C4—H4120.1C12—C17—H17119.9
O2—C5—C4117.8 (3)Sn—C18—H18A109.5
O2—C5—C6122.6 (3)Sn—C18—H18B109.5
C4—C5—C6119.6 (4)H18A—C18—H18B109.5
C7—C6—C5120.0 (3)Sn—C18—H18C109.5
C7—C6—H6120.0H18A—C18—H18C109.5
C5—C6—H6120.0H18B—C18—H18C109.5
C6—C7—C2120.7 (4)Sn—C19—H19A109.5
C6—C7—H7119.7Sn—C19—H19B109.5
C2—C7—H7119.7H19A—C19—H19B109.5
N2—C8—C10123.3 (3)Sn—C19—H19C109.5
N2—C8—C9119.0 (4)H19A—C19—H19C109.5
C10—C8—C9117.7 (4)H19B—C19—H19C109.5
C8—C9—H9A109.5
O3—Sn—O1—C117.4 (4)C3—C4—C5—O2179.6 (3)
C18—Sn—O1—C1116.5 (3)C3—C4—C5—C61.3 (6)
C19—Sn—O1—C1117.4 (3)O2—C5—C6—C7179.7 (3)
N2—Sn—O1—C16.8 (2)C4—C5—C6—C71.2 (6)
C18—Sn—O3—C11158.3 (3)C5—C6—C7—C20.3 (6)
C19—Sn—O3—C1176.6 (3)C3—C2—C7—C61.7 (5)
N2—Sn—O3—C1135.0 (3)C1—C2—C7—C6175.6 (3)
O1—Sn—O3—C1158.3 (4)N1—N2—C8—C10179.9 (3)
C1—N1—N2—C8168.5 (3)Sn—N2—C8—C108.0 (5)
C1—N1—N2—Sn4.2 (4)N1—N2—C8—C91.2 (5)
O3—Sn—N2—C824.1 (3)Sn—N2—C8—C9170.7 (3)
C18—Sn—N2—C8110.2 (3)N2—C8—C10—C1111.3 (6)
C19—Sn—N2—C872.3 (3)C9—C8—C10—C11170.0 (4)
O1—Sn—N2—C8165.9 (3)Sn—O3—C11—C1030.7 (5)
O3—Sn—N2—N1164.0 (3)Sn—O3—C11—C12151.4 (3)
C18—Sn—N2—N178.0 (3)C8—C10—C11—O30.6 (6)
C19—Sn—N2—N199.5 (3)C8—C10—C11—C12178.3 (4)
O1—Sn—N2—N15.9 (2)O3—C11—C12—C13150.4 (4)
N2—N1—C1—O12.4 (5)C10—C11—C12—C1331.7 (5)
N2—N1—C1—C2176.3 (3)O3—C11—C12—C1726.3 (5)
Sn—O1—C1—N17.7 (5)C10—C11—C12—C17151.6 (4)
Sn—O1—C1—C2171.1 (2)C17—C12—C13—C140.5 (6)
N1—C1—C2—C3167.5 (3)C11—C12—C13—C14176.2 (4)
O1—C1—C2—C313.7 (5)C12—C13—C14—C151.1 (6)
N1—C1—C2—C715.3 (5)C13—C14—C15—C160.6 (6)
O1—C1—C2—C7163.5 (3)C14—C15—C16—C170.6 (6)
C7—C2—C3—C41.7 (6)C15—C16—C17—C121.3 (6)
C1—C2—C3—C4175.6 (3)C13—C12—C17—C160.7 (6)
C2—C3—C4—C50.2 (6)C11—C12—C17—C16177.5 (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···AD—HH···AD···AD—H···A
O2—H2o···O1i0.841.912.702 (3)156
C4—H4···Cg1ii0.952.913.624 (4)133
C9—H9c···Cg2iii0.982.883.777 (4)152
C16—H16···Cg3iv0.952.893.668 (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, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formula[Sn(CH3)2(C17H14N2O3)]
Mr443.06
Crystal system, space groupMonoclinic, P21/c
Temperature (K)150
a, b, c (Å)8.0784 (2), 20.5410 (5), 11.1678 (3)
β (°) 93.025 (2)
V3)1850.58 (8)
Z4
Radiation typeCu Kα
µ (mm1)11.15
Crystal size (mm)0.22 × 0.16 × 0.10
Data collection
DiffractometerAgilent SuperNova Dual
diffractometer with an Atlas detector
Absorption correctionAnalytical
(CrysAlis PRO; Agilent, 2011)
Tmin, Tmax0.696, 0.822
No. of measured, independent and
observed [I > 2σ(I)] reflections
5718, 3124, 2690
Rint0.038
(sin θ/λ)max1)0.588
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.081, 1.00
No. of reflections3124
No. of parameters230
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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—O12.156 (3)Sn—C182.105 (4)
Sn—O32.099 (3)Sn—C192.112 (4)
Sn—N22.148 (3)
O1—Sn—O3155.08 (10)C18—Sn—C19124.65 (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···AD—HH···AD···AD—H···A
O2—H2o···O1i0.841.912.702 (3)156
C4—H4···Cg1ii0.952.913.624 (4)133
C9—H9c···Cg2iii0.982.883.777 (4)152
C16—H16···Cg3iv0.952.893.668 (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, y1/2, 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

First citationAddison, 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
First citationAffan, 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
First citationAffan, 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
First citationAffan, 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
First citationAgilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Oxford, UK.  Google Scholar
First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds