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The Sn atom in the title complex, [Sn2(C7H6Cl)4(C10H8N2O3)2(C2H6O)2], has a distorted penta­gonal–bipyramidal configuration, being coordinated by three O atoms and one N atom from the pyruvic acid benzoyl­hydrazone ligands, one O atom of an ethanol mol­ecule and two axial C atoms from trans 4-chloro­benz­yl groups, thus forming a dimeric mol­ecule, which has crystallographic \overline{1} symmetry. Intra­molecular hydrogen bonds contribute to the stability and compactness of the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805016910/br6193sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805016910/br6193Isup2.hkl
Contains datablock I

CCDC reference: 277197

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • R factor = 0.034
  • wR factor = 0.106
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

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Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Bis[µ-pyruvic acid benzoylhydrazonato(2-)]bis[bis(4-chlorobenzyl)ethanoltin(IV)] top
Crystal data top
[Sn2(C7H6Cl)4(C10H8N2O3)2(C2H6O)2]F(000) = 1248
Mr = 1240.16Dx = 1.538 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5918 reflections
a = 10.4162 (14) Åθ = 2.3–27.3°
b = 16.693 (2) ŵ = 1.19 mm1
c = 15.536 (2) ÅT = 298 K
β = 97.474 (2)°Block, colorless
V = 2678.4 (6) Å30.53 × 0.47 × 0.34 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
4723 independent reflections
Radiation source: fine-focus sealed tube3591 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
φ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.572, Tmax = 0.688k = 1919
13835 measured reflectionsl = 1218
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.06P)2 + 2.1458P]
where P = (Fo2 + 2Fc2)/3
4723 reflections(Δ/σ)max = 0.001
319 parametersΔρmax = 0.65 e Å3
32 restraintsΔρmin = 0.54 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.59198 (3)0.953748 (18)0.897103 (19)0.04383 (14)
Cl10.8216 (3)1.12013 (15)0.52980 (14)0.1343 (10)
Cl20.14398 (17)0.71106 (11)0.65341 (10)0.0882 (5)
N10.4458 (4)0.9664 (2)0.7792 (2)0.0429 (9)
N20.4825 (4)0.9452 (2)0.7006 (2)0.0491 (10)
O10.3979 (3)1.00750 (18)0.93462 (18)0.0447 (7)
O20.1893 (3)1.0282 (2)0.8838 (2)0.0636 (10)
O30.6683 (3)0.90264 (19)0.7874 (2)0.0510 (8)
O40.8070 (4)0.9172 (3)0.9579 (3)0.0701 (11)
C10.3026 (5)1.0104 (3)0.8742 (3)0.0477 (11)
C20.3294 (5)0.9892 (3)0.7840 (3)0.0475 (11)
C30.2244 (5)0.9928 (4)0.7096 (3)0.0701 (16)
H3A0.25810.97730.65740.105*
H3B0.19131.04640.70350.105*
H3C0.15600.95690.71980.105*
C40.5998 (5)0.9143 (3)0.7129 (3)0.0462 (11)
C50.6595 (5)0.8928 (3)0.6347 (3)0.0514 (12)
C60.5984 (6)0.9112 (3)0.5526 (3)0.0626 (14)
H60.51580.93340.54620.075*
C70.6589 (7)0.8970 (4)0.4801 (4)0.0768 (17)
H70.61750.91070.42530.092*
C80.7784 (7)0.8631 (4)0.4882 (4)0.0796 (18)
H80.81930.85390.43930.095*
C90.8380 (8)0.8428 (5)0.5687 (4)0.103 (3)
H90.91900.81840.57460.123*
C100.7787 (7)0.8583 (4)0.6417 (4)0.086 (2)
H100.82080.84490.69630.104*
C110.6752 (6)1.0709 (3)0.8878 (3)0.0588 (13)
H11A0.61191.11110.89870.071*
H11B0.74931.07640.93210.071*
C120.7170 (5)1.0857 (3)0.8010 (3)0.0532 (12)
C130.8348 (5)1.0593 (3)0.7788 (4)0.0683 (15)
H130.89321.03380.82040.082*
C140.8668 (7)1.0705 (4)0.6955 (5)0.081 (2)
H140.94601.05270.68150.097*
C150.7820 (7)1.1074 (4)0.6351 (4)0.0760 (18)
C160.6682 (7)1.1349 (4)0.6546 (4)0.0800 (18)
H160.61201.16150.61270.096*
C170.6349 (5)1.1238 (3)0.7358 (4)0.0677 (15)
H170.55501.14220.74800.081*
C180.5291 (5)0.8395 (3)0.9397 (3)0.0490 (11)
H18A0.60310.80410.95160.059*
H18B0.49140.84640.99310.059*
C190.4323 (5)0.8028 (2)0.8729 (3)0.0432 (10)
C200.3004 (5)0.8150 (3)0.8722 (3)0.0528 (12)
H200.27160.84350.91750.063*
C210.2106 (5)0.7861 (3)0.8061 (3)0.0587 (13)
H210.12260.79530.80630.070*
C220.2543 (5)0.7437 (3)0.7403 (3)0.0553 (13)
C230.3828 (5)0.7278 (3)0.7400 (3)0.0577 (13)
H230.41010.69720.69570.069*
C240.4716 (5)0.7574 (3)0.8056 (3)0.0514 (12)
H240.55920.74710.80500.062*
C250.8828 (9)0.8540 (6)0.9400 (6)0.139 (3)
H25A0.90830.86400.88310.167*
H25B0.82710.80720.93420.167*
C260.9962 (9)0.8314 (6)0.9944 (6)0.138 (3)
H26A1.03400.78560.97020.166*
H26B0.97470.81841.05100.166*
H26C1.05680.87500.99900.166*
H10.815 (6)0.935 (4)1.010 (4)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0485 (2)0.0460 (2)0.0351 (2)0.00050 (14)0.00211 (13)0.00340 (14)
Cl10.198 (2)0.1359 (18)0.0818 (13)0.0685 (17)0.0659 (15)0.0144 (12)
Cl20.0881 (11)0.1016 (12)0.0678 (10)0.0266 (9)0.0163 (8)0.0189 (9)
N10.052 (2)0.044 (2)0.0315 (19)0.0010 (17)0.0015 (17)0.0006 (15)
N20.058 (3)0.053 (2)0.035 (2)0.0042 (19)0.0022 (18)0.0005 (17)
O10.0480 (18)0.0499 (18)0.0339 (16)0.0050 (15)0.0035 (14)0.0040 (14)
O20.048 (2)0.095 (3)0.046 (2)0.0117 (19)0.0012 (16)0.0144 (18)
O30.0546 (19)0.057 (2)0.0395 (18)0.0080 (16)0.0004 (15)0.0047 (15)
O40.059 (2)0.095 (3)0.053 (2)0.021 (2)0.0049 (18)0.028 (2)
C10.051 (3)0.050 (3)0.040 (3)0.000 (2)0.000 (2)0.000 (2)
C20.053 (3)0.052 (3)0.036 (2)0.002 (2)0.004 (2)0.002 (2)
C30.058 (3)0.112 (5)0.038 (3)0.013 (3)0.003 (2)0.001 (3)
C40.059 (3)0.042 (3)0.037 (3)0.003 (2)0.002 (2)0.004 (2)
C50.066 (3)0.048 (3)0.041 (3)0.003 (2)0.007 (2)0.003 (2)
C60.068 (3)0.075 (4)0.045 (3)0.005 (3)0.007 (3)0.001 (3)
C70.095 (5)0.093 (4)0.043 (3)0.006 (4)0.012 (3)0.006 (3)
C80.109 (5)0.082 (4)0.052 (4)0.013 (4)0.029 (4)0.010 (3)
C90.103 (5)0.140 (7)0.067 (4)0.053 (5)0.023 (4)0.005 (4)
C100.097 (5)0.111 (5)0.049 (3)0.040 (4)0.005 (3)0.002 (3)
C110.073 (4)0.051 (3)0.052 (3)0.011 (3)0.006 (3)0.008 (2)
C120.053 (3)0.049 (3)0.058 (3)0.011 (2)0.008 (2)0.008 (2)
C130.051 (3)0.070 (4)0.084 (4)0.004 (3)0.007 (3)0.004 (3)
C140.071 (4)0.081 (4)0.102 (5)0.010 (3)0.050 (4)0.007 (4)
C150.093 (5)0.072 (4)0.066 (4)0.029 (4)0.022 (4)0.006 (3)
C160.082 (4)0.080 (4)0.077 (4)0.010 (4)0.010 (4)0.022 (3)
C170.058 (3)0.070 (4)0.077 (4)0.004 (3)0.017 (3)0.014 (3)
C180.065 (3)0.044 (3)0.036 (2)0.005 (2)0.003 (2)0.002 (2)
C190.059 (3)0.032 (2)0.037 (2)0.001 (2)0.001 (2)0.0025 (18)
C200.062 (3)0.055 (3)0.044 (3)0.003 (2)0.014 (2)0.008 (2)
C210.055 (3)0.058 (3)0.063 (3)0.008 (2)0.008 (3)0.006 (3)
C220.068 (3)0.051 (3)0.044 (3)0.015 (2)0.005 (2)0.002 (2)
C230.073 (4)0.054 (3)0.046 (3)0.005 (3)0.008 (3)0.017 (2)
C240.054 (3)0.047 (3)0.053 (3)0.008 (2)0.005 (2)0.004 (2)
C250.135 (6)0.156 (7)0.113 (6)0.071 (5)0.036 (5)0.055 (5)
C260.112 (6)0.168 (7)0.128 (6)0.043 (6)0.006 (5)0.045 (6)
Geometric parameters (Å, º) top
Sn1—C182.148 (5)C10—H100.9300
Sn1—O32.148 (3)C11—C121.491 (7)
Sn1—C112.151 (5)C11—H11A0.9700
Sn1—N12.235 (4)C11—H11B0.9700
Sn1—O12.353 (3)C12—C131.388 (7)
Sn1—O42.394 (4)C12—C171.391 (8)
Sn1—O1i2.682 (2)C13—C141.391 (9)
Cl1—C151.751 (6)C13—H130.9300
Cl2—C221.742 (5)C14—C151.350 (10)
N1—C21.283 (6)C14—H140.9300
N1—N21.372 (5)C15—C161.342 (9)
N2—C41.318 (6)C16—C171.364 (8)
O1—C11.276 (5)C16—H160.9300
O2—C11.245 (6)C17—H170.9300
O3—C41.293 (5)C18—C191.482 (6)
O4—C251.368 (8)C18—H18A0.9700
O4—H10.85 (6)C18—H18B0.9700
C1—C21.506 (6)C19—C201.388 (7)
C2—C31.486 (7)C19—C241.395 (6)
C3—H3A0.9600C20—C211.384 (7)
C3—H3B0.9600C20—H200.9300
C3—H3C0.9600C21—C221.369 (7)
C4—C51.480 (6)C21—H210.9300
C5—C101.361 (8)C22—C231.365 (8)
C5—C61.384 (7)C23—C241.377 (7)
C6—C71.381 (7)C23—H230.9300
C6—H60.9300C24—H240.9300
C7—C81.359 (9)C25—C261.410 (10)
C7—H70.9300C25—H25A0.9700
C8—C91.366 (9)C25—H25B0.9700
C8—H80.9300C26—H26A0.9600
C9—C101.384 (8)C26—H26B0.9600
C9—H90.9300C26—H26C0.9600
C18—Sn1—O392.91 (16)C9—C10—H10119.5
C18—Sn1—C11165.72 (19)C12—C11—Sn1112.3 (3)
O3—Sn1—C1196.52 (17)C12—C11—H11A109.2
C18—Sn1—N197.67 (16)Sn1—C11—H11A109.2
O3—Sn1—N170.74 (13)C12—C11—H11B109.2
C11—Sn1—N195.55 (18)Sn1—C11—H11B109.2
C18—Sn1—O187.49 (16)H11A—C11—H11B107.9
O3—Sn1—O1140.03 (11)C13—C12—C17116.4 (5)
C11—Sn1—O192.10 (17)C13—C12—C11122.9 (5)
N1—Sn1—O169.61 (12)C17—C12—C11120.6 (5)
C18—Sn1—O487.67 (17)C12—C13—C14120.9 (6)
O3—Sn1—O477.74 (12)C12—C13—H13119.5
C11—Sn1—O483.9 (2)C14—C13—H13119.5
N1—Sn1—O4148.22 (14)C15—C14—C13119.6 (6)
O1—Sn1—O4142.12 (12)C15—C14—H14120.2
C18—Sn1—O1i83.63 (12)C13—C14—H14120.2
C11—Sn1—O1i83.18 (13)C16—C15—C14121.0 (6)
O3—Sn1—O1i153.83 (9)C16—C15—Cl1119.4 (6)
N1—Sn1—O1i135.47 (10)C14—C15—Cl1119.5 (6)
O1—Sn1—O1i65.95 (10)C15—C16—C17120.1 (6)
O4—Sn1—O1i76.14 (10)C15—C16—H16120.0
C2—N1—N2120.2 (4)C17—C16—H16120.0
C2—N1—Sn1121.9 (3)C16—C17—C12121.9 (6)
N2—N1—Sn1117.8 (3)C16—C17—H17119.0
C4—N2—N1109.3 (4)C12—C17—H17119.0
C1—O1—Sn1116.3 (3)C19—C18—Sn1111.0 (3)
C4—O3—Sn1115.6 (3)C19—C18—H18A109.4
C25—O4—Sn1130.7 (4)Sn1—C18—H18A109.4
C25—O4—H1118 (4)C19—C18—H18B109.4
Sn1—O4—H1105 (4)Sn1—C18—H18B109.4
O2—C1—O1125.5 (4)H18A—C18—H18B108.0
O2—C1—C2117.4 (4)C20—C19—C24117.5 (4)
O1—C1—C2117.1 (4)C20—C19—C18121.8 (4)
N1—C2—C3124.9 (4)C24—C19—C18120.7 (4)
N1—C2—C1114.5 (4)C21—C20—C19121.8 (5)
C3—C2—C1120.5 (4)C21—C20—H20119.1
C2—C3—H3A109.5C19—C20—H20119.1
C2—C3—H3B109.5C22—C21—C20118.5 (5)
H3A—C3—H3B109.5C22—C21—H21120.8
C2—C3—H3C109.5C20—C21—H21120.8
H3A—C3—H3C109.5C23—C22—C21121.6 (5)
H3B—C3—H3C109.5C23—C22—Cl2119.0 (4)
O3—C4—N2125.7 (4)C21—C22—Cl2119.4 (4)
O3—C4—C5117.2 (4)C22—C23—C24119.5 (5)
N2—C4—C5117.1 (4)C22—C23—H23120.3
C10—C5—C6118.3 (5)C24—C23—H23120.3
C10—C5—C4120.9 (5)C23—C24—C19121.1 (5)
C6—C5—C4120.8 (5)C23—C24—H24119.5
C7—C6—C5120.7 (6)C19—C24—H24119.5
C7—C6—H6119.7O4—C25—C26123.0 (7)
C5—C6—H6119.7O4—C25—H25A106.6
C8—C7—C6120.4 (6)C26—C25—H25A106.6
C8—C7—H7119.8O4—C25—H25B106.6
C6—C7—H7119.8C26—C25—H25B106.6
C7—C8—C9119.4 (6)H25A—C25—H25B106.5
C7—C8—H8120.3C25—C26—H26A109.5
C9—C8—H8120.3C25—C26—H26B109.5
C8—C9—C10120.4 (6)H26A—C26—H26B109.5
C8—C9—H9119.8C25—C26—H26C109.5
C10—C9—H9119.8H26A—C26—H26C109.5
C5—C10—C9120.9 (6)H26B—C26—H26C109.5
C5—C10—H10119.5
Symmetry code: (i) x+1, y+2, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H1···O2i0.85 (6)1.77 (6)2.619 (5)173 (6)
Symmetry code: (i) x+1, y+2, z+2.
 

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