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Di­cyclo­hexyl­{3-hydr­­oxy-N′-[1-(2-oxido­phenyl-κO)ethyl­­idene]-2-naphthohydrazidato-κ2N′,O}tin(IV)

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 10 February 2010; accepted 12 February 2010; online 17 February 2010)

In the title compound, [Sn(C6H11)2(C19H14N2O3)], the SnIV atom is O,N,O′ chelated by the deprotonated Schiff base ligand and exists in a cis-trigonal-bipyramidal environment, completed by the two cyclohexyl ligands.

Related literature

For other dialkyl­tin(IV) compounds with similar Schiff-base ligands, see: Lee et al. (2009a[Lee, S. M., Lo, K. M., Mohd Ali, H. & Ng, S. W. (2009a). Acta Cryst. E65, m816.],b[Lee, S. M., Lo, K. M., Ali, H. M. & Ng, S. W. (2009b). Acta Cryst. E65, m862.],c[Lee, S. M., Lo, K. M., Ali, H. M. & Ng, S. W. (2009c). Acta Cryst. E65, m863.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(C6H11)2(C19H14N2O3)]

  • Mr = 603.31

  • Monoclinic, C 2/c

  • a = 30.2358 (4) Å

  • b = 7.7030 (1) Å

  • c = 25.8528 (4) Å

  • β = 111.249 (2)°

  • V = 5611.92 (16) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.95 mm−1

  • T = 293 K

  • 0.30 × 0.10 × 0.10 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.765, Tmax = 0.912

  • 26097 measured reflections

  • 6424 independent reflections

  • 3942 reflections with I > 2σ(I)

  • Rint = 0.047

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.111

  • S = 1.00

  • 6424 reflections

  • 336 parameters

  • H-atom parameters constrained

  • Δρmax = 0.52 e Å−3

  • Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). publCIF. In preparation.]).

Supporting information


Related literature top

For other dialkyltin(IV) compounds with similar Schiff-base ligands, see: Lee et al. (2009a,b,c).

Experimental top

The Schiff base ligand was prepared by the condensation of 3-hydroxy-2-naphthoiyl hydrazide with 2-hydroxyacetophenone. The organotin compound was prepared by heating the Schiff base (0.64 g, 2 mmol) and dicyclohexyltin oxide (0.6 g, 2mmol) in toluene for 3 h. After filtering the solution, yellow crystals were obtained upon evaporation of the filtrate.

Refinement top

H atoms were placed at calculated positions (C–H = 0.93–0.98 Å and O–H = 0.82 Å) and were treated as riding on their parent atoms, with U(H) set to 1.2–1.5 times Ueq(C,O).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).

Figures top
[Figure 1] Fig. 1. Displacement ellipsoid plot (Barbour, 2001) of [Sn(C6H11)2(C9H14N2O3)] at the 50% probability level. H atoms are drawn as spheres of arbitrary radius.
Dicyclohexyl{3-hydroxy-N'-[1-(2-oxidophenyl-κO)ethylidene]-2- naphthohydrazidato-κ2N',O}tin(IV) top
Crystal data top
[Sn(C6H11)2(C19H14N2O3)]F(000) = 2480
Mr = 603.31Dx = 1.428 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4113 reflections
a = 30.2358 (4) Åθ = 2.6–20.3°
b = 7.7030 (1) ŵ = 0.95 mm1
c = 25.8528 (4) ÅT = 293 K
β = 111.249 (2)°Block, yellow
V = 5611.92 (16) Å30.30 × 0.10 × 0.10 mm
Z = 8
Data collection top
Bruker SMART APEX
diffractometer
6424 independent reflections
Radiation source: fine-focus sealed tube3942 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 3939
Tmin = 0.765, Tmax = 0.912k = 1010
26097 measured reflectionsl = 3333
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.047P)2 + 3.9403P]
where P = (Fo2 + 2Fc2)/3
6424 reflections(Δ/σ)max = 0.001
336 parametersΔρmax = 0.52 e Å3
0 restraintsΔρmin = 0.43 e Å3
Crystal data top
[Sn(C6H11)2(C19H14N2O3)]V = 5611.92 (16) Å3
Mr = 603.31Z = 8
Monoclinic, C2/cMo Kα radiation
a = 30.2358 (4) ŵ = 0.95 mm1
b = 7.7030 (1) ÅT = 293 K
c = 25.8528 (4) Å0.30 × 0.10 × 0.10 mm
β = 111.249 (2)°
Data collection top
Bruker SMART APEX
diffractometer
6424 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3942 reflections with I > 2σ(I)
Tmin = 0.765, Tmax = 0.912Rint = 0.047
26097 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.111H-atom parameters constrained
S = 1.00Δρmax = 0.52 e Å3
6424 reflectionsΔρmin = 0.43 e Å3
336 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.607817 (9)0.32667 (4)0.446538 (11)0.06297 (12)
O10.59313 (11)0.1555 (4)0.38108 (11)0.0778 (8)
O20.65161 (9)0.5072 (4)0.50781 (11)0.0713 (7)
O30.79451 (10)0.5522 (5)0.52370 (13)0.0853 (9)
H30.77280.50300.49940.128*
N10.67212 (11)0.3711 (4)0.42833 (13)0.0574 (8)
N20.70928 (10)0.4444 (4)0.47247 (13)0.0589 (8)
C10.61233 (16)0.1276 (6)0.50638 (17)0.0735 (11)
H10.63940.05570.50750.088*
C20.6237 (3)0.1871 (7)0.5631 (2)0.134 (3)
H2A0.59980.26960.56410.161*
H2B0.65400.24700.57530.161*
C30.6262 (3)0.0403 (9)0.6031 (2)0.159 (3)
H3A0.65460.02760.60850.191*
H3B0.62890.08910.63870.191*
C40.5843 (3)0.0760 (9)0.5836 (2)0.137 (3)
H4A0.58990.17500.60830.165*
H4B0.55690.01410.58520.165*
C50.5741 (2)0.1371 (6)0.5276 (2)0.1075 (18)
H5A0.54460.20170.51550.129*
H5B0.59910.21610.52740.129*
C60.57024 (18)0.0080 (6)0.48669 (18)0.0939 (15)
H6A0.56770.04150.45120.113*
H6B0.54160.07420.48120.113*
C70.55119 (15)0.5063 (6)0.41036 (17)0.0755 (11)
H70.55410.59650.43810.091*
C80.50407 (19)0.4219 (9)0.3978 (4)0.163 (3)
H8A0.50220.37640.43190.196*
H8B0.50130.32490.37280.196*
C90.4627 (2)0.5467 (11)0.3712 (4)0.189 (4)
H9A0.43310.48280.36070.227*
H9B0.46250.63390.39820.227*
C100.4659 (2)0.6324 (9)0.3222 (3)0.154 (3)
H10A0.44060.71710.30850.185*
H10B0.46160.54690.29330.185*
C110.5115 (3)0.7192 (8)0.3344 (3)0.138 (2)
H11A0.51410.81460.35980.166*
H11B0.51300.76700.30040.166*
C120.5529 (2)0.5950 (8)0.3600 (3)0.124 (2)
H12A0.55260.50820.33270.149*
H12B0.58240.65910.36980.149*
C130.60322 (16)0.1758 (5)0.33577 (16)0.0663 (10)
C140.57067 (18)0.1090 (6)0.28635 (18)0.0838 (13)
H140.54280.05810.28630.101*
C150.5795 (2)0.1180 (7)0.2377 (2)0.1016 (17)
H150.55750.07370.20510.122*
C160.6205 (2)0.1918 (7)0.2375 (2)0.1091 (19)
H160.62650.19710.20470.131*
C170.65253 (19)0.2574 (6)0.28514 (19)0.0844 (14)
H170.68020.30740.28420.101*
C180.64529 (15)0.2524 (5)0.33554 (16)0.0633 (10)
C190.68174 (14)0.3258 (4)0.38474 (16)0.0592 (9)
C200.73134 (15)0.3514 (5)0.38609 (19)0.0770 (12)
H20A0.75360.31100.42090.115*
H20B0.73670.47250.38180.115*
H20C0.73550.28700.35640.115*
C210.69499 (13)0.5079 (5)0.51059 (16)0.0572 (9)
C220.73168 (13)0.5798 (5)0.56094 (15)0.0555 (9)
C230.78029 (14)0.5961 (5)0.56581 (17)0.0626 (10)
C240.81286 (15)0.6568 (5)0.61388 (19)0.0742 (12)
H240.84430.66720.61660.089*
C250.80107 (15)0.7043 (5)0.65944 (18)0.0681 (11)
C260.83469 (19)0.7662 (7)0.7099 (2)0.0911 (15)
H260.86640.77450.71390.109*
C270.8213 (2)0.8136 (6)0.7525 (2)0.1030 (18)
H270.84390.85510.78520.124*
C280.7746 (2)0.8012 (6)0.7481 (2)0.0982 (17)
H280.76590.83460.77760.118*
C290.74128 (18)0.7402 (6)0.70071 (19)0.0833 (13)
H290.70990.73130.69830.100*
C300.75344 (15)0.6904 (5)0.65528 (17)0.0658 (10)
C310.71993 (14)0.6266 (5)0.60520 (16)0.0634 (10)
H310.68850.61590.60230.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.05673 (17)0.0795 (2)0.05493 (17)0.00534 (14)0.02301 (13)0.00016 (14)
O10.083 (2)0.095 (2)0.0615 (17)0.0239 (16)0.0339 (15)0.0086 (15)
O20.0561 (16)0.086 (2)0.0739 (17)0.0072 (14)0.0266 (14)0.0162 (15)
O30.0598 (18)0.116 (3)0.085 (2)0.0003 (17)0.0322 (17)0.0030 (18)
N10.0606 (19)0.0569 (19)0.0572 (18)0.0028 (14)0.0243 (16)0.0065 (14)
N20.0561 (19)0.061 (2)0.0605 (19)0.0022 (15)0.0226 (16)0.0075 (15)
C10.073 (3)0.093 (3)0.061 (2)0.004 (2)0.032 (2)0.004 (2)
C20.196 (7)0.126 (5)0.064 (3)0.078 (4)0.028 (4)0.000 (3)
C30.223 (8)0.165 (6)0.058 (3)0.083 (6)0.014 (4)0.016 (4)
C40.201 (7)0.139 (5)0.073 (4)0.058 (5)0.052 (4)0.008 (3)
C50.151 (5)0.095 (4)0.084 (4)0.030 (3)0.050 (4)0.002 (3)
C60.108 (4)0.102 (4)0.065 (3)0.033 (3)0.024 (3)0.002 (3)
C70.073 (3)0.083 (3)0.065 (3)0.006 (2)0.019 (2)0.000 (2)
C80.069 (4)0.155 (6)0.271 (9)0.025 (4)0.068 (5)0.112 (6)
C90.080 (4)0.181 (8)0.299 (11)0.028 (5)0.061 (6)0.110 (8)
C100.105 (5)0.104 (5)0.185 (8)0.004 (4)0.030 (5)0.023 (5)
C110.130 (6)0.107 (5)0.153 (6)0.019 (4)0.021 (5)0.051 (4)
C120.104 (4)0.117 (4)0.150 (6)0.003 (4)0.043 (4)0.049 (4)
C130.083 (3)0.064 (2)0.056 (2)0.000 (2)0.030 (2)0.0012 (19)
C140.101 (4)0.085 (3)0.065 (3)0.023 (3)0.030 (3)0.013 (2)
C150.135 (5)0.103 (4)0.063 (3)0.021 (3)0.031 (3)0.017 (3)
C160.159 (6)0.115 (4)0.069 (3)0.038 (4)0.060 (4)0.019 (3)
C170.116 (4)0.081 (3)0.071 (3)0.016 (3)0.052 (3)0.006 (2)
C180.085 (3)0.053 (2)0.061 (2)0.005 (2)0.036 (2)0.0049 (18)
C190.072 (2)0.050 (2)0.063 (2)0.0068 (19)0.033 (2)0.0122 (18)
C200.078 (3)0.080 (3)0.087 (3)0.009 (2)0.047 (3)0.010 (2)
C210.057 (2)0.052 (2)0.063 (2)0.0032 (18)0.0227 (19)0.0066 (18)
C220.053 (2)0.052 (2)0.061 (2)0.0032 (17)0.0207 (19)0.0114 (17)
C230.057 (2)0.061 (2)0.069 (3)0.0050 (18)0.022 (2)0.012 (2)
C240.054 (2)0.073 (3)0.086 (3)0.006 (2)0.014 (2)0.012 (2)
C250.071 (3)0.053 (2)0.068 (3)0.0006 (19)0.009 (2)0.0097 (19)
C260.078 (3)0.090 (3)0.085 (4)0.000 (3)0.004 (3)0.005 (3)
C270.116 (5)0.089 (4)0.076 (3)0.015 (3)0.002 (3)0.000 (3)
C280.130 (5)0.093 (4)0.068 (3)0.022 (3)0.031 (3)0.013 (3)
C290.094 (4)0.083 (3)0.076 (3)0.015 (3)0.035 (3)0.006 (2)
C300.076 (3)0.052 (2)0.064 (2)0.0053 (19)0.018 (2)0.0067 (19)
C310.061 (2)0.059 (2)0.070 (3)0.0011 (18)0.024 (2)0.0052 (19)
Geometric parameters (Å, º) top
Sn1—O12.063 (3)C10—H10B0.97
Sn1—C72.136 (4)C11—C121.523 (8)
Sn1—C12.147 (4)C11—H11A0.97
Sn1—O22.162 (3)C11—H11B0.97
Sn1—N12.187 (3)C12—H12A0.97
O1—C131.322 (5)C12—H12B0.97
O2—C211.287 (4)C13—C181.404 (6)
O3—C231.350 (5)C13—C141.398 (6)
O3—H30.82C14—C151.378 (6)
N1—C191.309 (5)C14—H140.93
N1—N21.398 (4)C15—C161.367 (8)
N2—C211.306 (5)C15—H150.93
C1—C21.455 (6)C16—C171.359 (7)
C1—C61.502 (6)C16—H160.93
C1—H10.98C17—C181.398 (6)
C2—C31.515 (7)C17—H170.93
C2—H2A0.97C18—C191.461 (6)
C2—H2B0.97C19—C201.501 (5)
C3—C41.483 (8)C20—H20A0.96
C3—H3A0.97C20—H20B0.96
C3—H3B0.97C20—H20C0.96
C4—C51.447 (7)C21—C221.478 (5)
C4—H4A0.97C22—C311.364 (5)
C4—H4B0.97C22—C231.434 (5)
C5—C61.514 (6)C23—C241.358 (6)
C5—H5A0.97C24—C251.397 (6)
C5—H5B0.97C24—H240.93
C6—H6A0.97C25—C301.409 (6)
C6—H6B0.97C25—C261.415 (6)
C7—C121.487 (7)C26—C271.354 (7)
C7—C81.491 (7)C26—H260.93
C7—H70.98C27—C281.377 (8)
C8—C91.529 (8)C27—H270.93
C8—H8A0.97C28—C291.357 (6)
C8—H8B0.97C28—H280.93
C9—C101.463 (10)C29—C301.405 (6)
C9—H9A0.97C29—H290.93
C9—H9B0.97C30—C311.412 (5)
C10—C111.460 (9)C31—H310.93
C10—H10A0.97
O1—Sn1—C798.91 (14)C11—C10—H10B109.2
O1—Sn1—C194.19 (15)H10A—C10—H10B107.9
C7—Sn1—C1127.59 (17)C10—C11—C12111.6 (5)
O1—Sn1—O2154.78 (11)C10—C11—H11A109.3
C7—Sn1—O294.88 (14)C12—C11—H11A109.3
C1—Sn1—O293.98 (14)C10—C11—H11B109.3
O1—Sn1—N182.38 (11)C12—C11—H11B109.3
C7—Sn1—N1116.00 (14)H11A—C11—H11B108.0
C1—Sn1—N1115.95 (14)C7—C12—C11112.7 (5)
O2—Sn1—N172.59 (11)C7—C12—H12A109.1
C13—O1—Sn1126.9 (2)C11—C12—H12A109.1
C21—O2—Sn1112.6 (2)C7—C12—H12B109.1
C23—O3—H3109.5C11—C12—H12B109.1
C19—N1—N2116.5 (3)H12A—C12—H12B107.8
C19—N1—Sn1129.5 (3)O1—C13—C18123.6 (4)
N2—N1—Sn1113.7 (2)O1—C13—C14117.0 (4)
C21—N2—N1112.3 (3)C18—C13—C14119.3 (4)
C2—C1—C6113.3 (4)C15—C14—C13120.7 (5)
C2—C1—Sn1115.6 (3)C15—C14—H14119.7
C6—C1—Sn1111.6 (3)C13—C14—H14119.7
C2—C1—H1105.0C16—C15—C14120.1 (5)
C6—C1—H1105.0C16—C15—H15119.9
Sn1—C1—H1105.0C14—C15—H15119.9
C1—C2—C3112.8 (5)C17—C16—C15120.0 (5)
C1—C2—H2A109.0C17—C16—H16120.0
C3—C2—H2A109.0C15—C16—H16120.0
C1—C2—H2B109.0C16—C17—C18122.3 (5)
C3—C2—H2B109.0C16—C17—H17118.8
H2A—C2—H2B107.8C18—C17—H17118.8
C4—C3—C2113.2 (5)C17—C18—C13117.6 (4)
C4—C3—H3A108.9C17—C18—C19118.5 (4)
C2—C3—H3A108.9C13—C18—C19123.9 (3)
C4—C3—H3B108.9N1—C19—C18121.3 (4)
C2—C3—H3B108.9N1—C19—C20118.5 (4)
H3A—C3—H3B107.8C18—C19—C20120.2 (4)
C5—C4—C3112.5 (5)C19—C20—H20A109.5
C5—C4—H4A109.1C19—C20—H20B109.5
C3—C4—H4A109.1H20A—C20—H20B109.5
C5—C4—H4B109.1C19—C20—H20C109.5
C3—C4—H4B109.1H20A—C20—H20C109.5
H4A—C4—H4B107.8H20B—C20—H20C109.5
C4—C5—C6113.2 (5)O2—C21—N2124.4 (4)
C4—C5—H5A108.9O2—C21—C22118.4 (3)
C6—C5—H5A108.9N2—C21—C22117.2 (3)
C4—C5—H5B108.9C31—C22—C23118.3 (4)
C6—C5—H5B108.9C31—C22—C21119.8 (3)
H5A—C5—H5B107.8C23—C22—C21121.9 (4)
C1—C6—C5112.0 (4)O3—C23—C24119.1 (4)
C1—C6—H6A109.2O3—C23—C22121.5 (4)
C5—C6—H6A109.2C24—C23—C22119.4 (4)
C1—C6—H6B109.2C23—C24—C25122.6 (4)
C5—C6—H6B109.2C23—C24—H24118.7
H6A—C6—H6B107.9C25—C24—H24118.7
C12—C7—C8110.0 (5)C24—C25—C30118.8 (4)
C12—C7—Sn1113.8 (3)C24—C25—C26123.2 (5)
C8—C7—Sn1111.3 (3)C30—C25—C26118.0 (5)
C12—C7—H7107.1C27—C26—C25120.9 (5)
C8—C7—H7107.1C27—C26—H26119.5
Sn1—C7—H7107.1C25—C26—H26119.5
C7—C8—C9112.7 (5)C26—C27—C28120.9 (5)
C7—C8—H8A109.1C26—C27—H27119.5
C9—C8—H8A109.1C28—C27—H27119.5
C7—C8—H8B109.1C29—C28—C27120.1 (5)
C9—C8—H8B109.1C29—C28—H28119.9
H8A—C8—H8B107.8C27—C28—H28119.9
C10—C9—C8111.8 (7)C28—C29—C30121.0 (5)
C10—C9—H9A109.3C28—C29—H29119.5
C8—C9—H9A109.3C30—C29—H29119.5
C10—C9—H9B109.3C25—C30—C29119.0 (4)
C8—C9—H9B109.3C25—C30—C31118.1 (4)
H9A—C9—H9B107.9C29—C30—C31122.9 (4)
C9—C10—C11112.0 (6)C22—C31—C30122.9 (4)
C9—C10—H10A109.2C22—C31—H31118.6
C11—C10—H10A109.2C30—C31—H31118.6
C9—C10—H10B109.2
C7—Sn1—O1—C1378.9 (4)Sn1—O1—C13—C14145.0 (3)
C1—Sn1—O1—C13152.0 (4)O1—C13—C14—C15177.2 (4)
O2—Sn1—O1—C1343.4 (5)C18—C13—C14—C150.1 (7)
N1—Sn1—O1—C1336.4 (3)C13—C14—C15—C160.4 (8)
O1—Sn1—O2—C219.9 (4)C14—C15—C16—C170.4 (9)
C7—Sn1—O2—C21133.0 (3)C15—C16—C17—C180.1 (9)
C1—Sn1—O2—C2198.7 (3)C16—C17—C18—C130.2 (7)
N1—Sn1—O2—C2117.3 (2)C16—C17—C18—C19179.8 (5)
O1—Sn1—N1—C1913.7 (3)O1—C13—C18—C17176.7 (4)
C7—Sn1—N1—C1982.5 (3)C14—C13—C18—C170.2 (6)
C1—Sn1—N1—C19104.7 (3)O1—C13—C18—C193.0 (6)
O2—Sn1—N1—C19169.5 (3)C14—C13—C18—C19179.9 (4)
O1—Sn1—N1—N2159.7 (2)N2—N1—C19—C18178.3 (3)
C7—Sn1—N1—N2104.0 (2)Sn1—N1—C19—C188.4 (5)
C1—Sn1—N1—N268.8 (3)N2—N1—C19—C201.5 (5)
O2—Sn1—N1—N217.1 (2)Sn1—N1—C19—C20171.8 (2)
C19—N1—N2—C21170.9 (3)C17—C18—C19—N1160.1 (4)
Sn1—N1—N2—C2114.8 (3)C13—C18—C19—N120.3 (6)
O1—Sn1—C1—C2178.9 (5)C17—C18—C19—C2019.7 (6)
C7—Sn1—C1—C276.5 (5)C13—C18—C19—C20159.9 (4)
O2—Sn1—C1—C222.8 (5)Sn1—O2—C21—N216.8 (5)
N1—Sn1—C1—C295.4 (5)Sn1—O2—C21—C22161.0 (2)
O1—Sn1—C1—C649.6 (3)N1—N2—C21—O21.3 (5)
C7—Sn1—C1—C655.0 (4)N1—N2—C21—C22176.5 (3)
O2—Sn1—C1—C6154.3 (3)O2—C21—C22—C316.7 (5)
N1—Sn1—C1—C6133.2 (3)N2—C21—C22—C31171.3 (3)
C6—C1—C2—C349.2 (8)O2—C21—C22—C23175.8 (3)
Sn1—C1—C2—C3179.9 (5)N2—C21—C22—C236.3 (5)
C1—C2—C3—C449.9 (10)C31—C22—C23—O3180.0 (4)
C2—C3—C4—C551.4 (9)C21—C22—C23—O32.4 (6)
C3—C4—C5—C652.4 (9)C31—C22—C23—C240.1 (5)
C2—C1—C6—C549.8 (6)C21—C22—C23—C24177.5 (4)
Sn1—C1—C6—C5177.6 (4)O3—C23—C24—C25179.7 (4)
C4—C5—C6—C151.4 (7)C22—C23—C24—C250.2 (6)
O1—Sn1—C7—C1262.2 (4)C23—C24—C25—C300.7 (6)
C1—Sn1—C7—C12164.5 (4)C23—C24—C25—C26179.4 (4)
O2—Sn1—C7—C1296.6 (4)C24—C25—C26—C27178.8 (4)
N1—Sn1—C7—C1223.6 (4)C30—C25—C26—C271.2 (7)
O1—Sn1—C7—C862.9 (5)C25—C26—C27—C280.7 (8)
C1—Sn1—C7—C839.4 (5)C26—C27—C28—C290.2 (8)
O2—Sn1—C7—C8138.3 (4)C27—C28—C29—C300.6 (8)
N1—Sn1—C7—C8148.7 (4)C24—C25—C30—C29179.1 (4)
C12—C7—C8—C952.2 (9)C26—C25—C30—C290.8 (6)
Sn1—C7—C8—C9179.4 (6)C24—C25—C30—C310.9 (5)
C7—C8—C9—C1053.5 (10)C26—C25—C30—C31179.2 (4)
C8—C9—C10—C1154.2 (10)C28—C29—C30—C250.1 (7)
C9—C10—C11—C1254.9 (10)C28—C29—C30—C31179.9 (4)
C8—C7—C12—C1152.9 (7)C23—C22—C31—C300.2 (6)
Sn1—C7—C12—C11178.7 (4)C21—C22—C31—C30177.8 (3)
C10—C11—C12—C754.9 (9)C25—C30—C31—C220.6 (6)
Sn1—O1—C13—C1838.1 (6)C29—C30—C31—C22179.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···N20.821.852.571 (4)147

Experimental details

Crystal data
Chemical formula[Sn(C6H11)2(C19H14N2O3)]
Mr603.31
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)30.2358 (4), 7.7030 (1), 25.8528 (4)
β (°) 111.249 (2)
V3)5611.92 (16)
Z8
Radiation typeMo Kα
µ (mm1)0.95
Crystal size (mm)0.30 × 0.10 × 0.10
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.765, 0.912
No. of measured, independent and
observed [I > 2σ(I)] reflections
26097, 6424, 3942
Rint0.047
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.111, 1.00
No. of reflections6424
No. of parameters336
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.52, 0.43

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

 

Acknowledgements

The authors thank the University of Malaya (RG020/09AFR) for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS
First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationLee, S. M., Lo, K. M., Mohd Ali, H. & Ng, S. W. (2009a). Acta Cryst. E65, m816.  Web of Science CSD CrossRef IUCr Journals
First citationLee, S. M., Lo, K. M., Ali, H. M. & Ng, S. W. (2009b). Acta Cryst. E65, m862.  Web of Science CSD CrossRef IUCr Journals
First citationLee, S. M., Lo, K. M., Ali, H. M. & Ng, S. W. (2009c). Acta Cryst. E65, m863.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWestrip, S. P. (2010). publCIF. In preparation.

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