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The 1,10-phenanthroline heterocycle in the centrosymmetric four-molecule aggregate [Sn(C2O2Cl3)(C6H5)3(H2O)]2·2C12H8N2 interacts with the water molecule of the trans-C3SnO2 trigonal-bipyramidal aqua­carboxyl­ato­tri­organotin molecule through the coordinated water mol­ecule through hydrogen bonds [Owater...N = 2.755 (2) and 2.758 (2) Å].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803015939/bt6308sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803015939/bt6308Isup2.hkl
Contains datablock I

CCDC reference: 221647

Key indicators

  • Single-crystal X-ray study
  • T = 168 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.023
  • wR factor = 0.062
  • Data-to-parameter ratio = 15.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.561 0.698 Tmin and Tmax expected: 0.433 0.698 RR = 1.297 Please check that your absorption correction is appropriate. REFLT_03 From the CIF: _diffrn_reflns_theta_max 26.40 From the CIF: _reflns_number_total 5840 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 6149 Completeness (_total/calc) 94.97% Alert C: < 95% complete PLAT_710 Alert C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 4 O1W -SN1 -O1 -C19 -161.00 0.50 1.555 1.555 1.555 1.555
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Bis(aquatrichloroacetatotriphenyltin).bis(1,10-phenanthroline) top
Crystal data top
[Sn(C2Cl3O2)(C6H5)3(H2O)]2·2C12H8N2Z = 1
Mr = 1421.16F(000) = 712
Triclinic, P1Dx = 1.578 Mg m3
a = 9.1542 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.2739 (7) ÅCell parameters from 7435 reflections
c = 14.4308 (9) Åθ = 1.9–26.4°
α = 67.559 (1)°µ = 1.16 mm1
β = 86.347 (1)°T = 168 K
γ = 89.490 (1)°Irregular fragment, colorless
V = 1495.4 (2) Å30.76 × 0.62 × 0.31 mm
Data collection top
Siemens P4
diffractometer/CCD SMART area-detector
5840 independent reflections
Radiation source: medium-focus sealed tube5252 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
φ and ω scansθmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.561, Tmax = 0.698k = 1515
18009 measured reflectionsl = 1118
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)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0412P)2]
where P = (Fo2 + 2Fc2)/3
5840 reflections(Δ/σ)max = 0.001
378 parametersΔρmax = 1.12 e Å3
1 restraintΔρmin = 0.75 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.31978 (1)0.79597 (1)0.31625 (1)0.02265 (6)
Cl10.07533 (8)1.10316 (7)0.02991 (5)0.05536 (19)
Cl20.36376 (8)1.18484 (8)0.03935 (6)0.0673 (2)
Cl30.1120 (1)1.27476 (7)0.11458 (7)0.0822 (3)
O1w0.4334 (2)0.6297 (1)0.4204 (1)0.0264 (3)
O10.2108 (2)0.9469 (1)0.2062 (1)0.0303 (3)
O20.2237 (2)1.0789 (2)0.2775 (1)0.0434 (4)
N10.7026 (2)0.5877 (2)0.3444 (1)0.0278 (4)
N20.5338 (2)0.3877 (2)0.3861 (1)0.0281 (4)
C10.3071 (2)0.7102 (2)0.2139 (2)0.0241 (4)
C20.3083 (2)0.5875 (2)0.2472 (2)0.0295 (5)
C30.3055 (3)0.5317 (2)0.1805 (2)0.0354 (5)
C40.3014 (3)0.5981 (2)0.0785 (2)0.0368 (5)
C50.2985 (2)0.7200 (2)0.0441 (2)0.0348 (5)
C60.3012 (2)0.7758 (2)0.1107 (2)0.0282 (5)
C70.1631 (2)0.7643 (2)0.4393 (2)0.0247 (4)
C80.1010 (2)0.6523 (2)0.4899 (2)0.0312 (5)
C90.0017 (2)0.6288 (2)0.5715 (2)0.0373 (5)
C100.0367 (3)0.7174 (2)0.6049 (2)0.0405 (6)
C110.0242 (3)0.8286 (2)0.5562 (2)0.0458 (6)
C120.1225 (3)0.8528 (2)0.4735 (2)0.0386 (6)
C130.5140 (2)0.8980 (2)0.2992 (2)0.0282 (5)
C140.5608 (3)0.9284 (2)0.3756 (2)0.0344 (5)
C150.6948 (3)0.9852 (2)0.3653 (2)0.0508 (7)
C160.7827 (3)1.0136 (2)0.2782 (3)0.0568 (8)
C170.7370 (3)0.9866 (2)0.2012 (2)0.0529 (8)
C180.6034 (3)0.9292 (2)0.2108 (2)0.0403 (6)
C190.2085 (2)1.0499 (2)0.2081 (2)0.0272 (5)
C200.1896 (2)1.1492 (2)0.1023 (2)0.0322 (5)
C210.7296 (2)0.5205 (2)0.2894 (2)0.0267 (4)
C220.7911 (2)0.6790 (2)0.3277 (2)0.0322 (5)
C230.9099 (2)0.7118 (2)0.2553 (2)0.0389 (6)
C240.9345 (2)0.6466 (2)0.1979 (2)0.0390 (6)
C250.8438 (2)0.5493 (2)0.2131 (2)0.0331 (5)
C260.8637 (3)0.4770 (2)0.1557 (2)0.0433 (6)
C270.7743 (3)0.3850 (3)0.1711 (2)0.0449 (6)
C280.6562 (3)0.3536 (2)0.2466 (2)0.0362 (5)
C290.5561 (3)0.2610 (2)0.2625 (2)0.0461 (7)
C300.4475 (3)0.2348 (2)0.3373 (2)0.0459 (6)
C310.4422 (3)0.2999 (2)0.3980 (2)0.0364 (5)
C320.6370 (2)0.4187 (2)0.3087 (2)0.0279 (5)
H1w10.514 (2)0.604 (2)0.398 (2)0.040 (7)*
H1w20.436 (3)0.614 (2)0.485 (1)0.034 (7)*
H20.31100.54170.31700.035*
H30.30650.44800.20430.042*
H40.30050.56010.03220.044*
H50.29460.76540.02570.042*
H60.29910.85940.08640.034*
H80.12770.59070.46780.037*
H90.04020.55200.60450.045*
H100.10470.70170.66120.049*
H110.00160.88930.57950.055*
H120.16240.93020.44000.046*
H140.50050.91010.43580.041*
H150.72591.00460.41870.061*
H160.87481.05170.27170.068*
H170.79691.00730.14060.063*
H180.57280.91100.15660.048*
H220.77310.72520.36700.039*
H230.97120.77750.24670.047*
H241.01310.66710.14770.047*
H260.94200.49460.10550.052*
H270.78980.33960.13090.054*
H290.56410.21660.22110.055*
H300.37760.17390.34760.055*
H310.36820.28000.45130.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.02286 (8)0.02318 (8)0.02361 (8)0.0011 (1)0.0011 (1)0.01092 (6)
Cl10.0556 (4)0.0582 (4)0.0397 (3)0.0099 (3)0.0188 (3)0.0021 (3)
Cl20.0386 (4)0.0844 (6)0.0547 (4)0.0140 (4)0.0111 (3)0.0013 (4)
Cl30.1327 (9)0.0408 (4)0.0704 (5)0.0414 (5)0.0111 (5)0.0184 (4)
O1w0.025 (1)0.030 (1)0.025 (1)0.006 (1)0.003 (1)0.011 (1)
O10.034 (1)0.025 (1)0.033 (1)0.005 (1)0.009 (1)0.011 (1)
O20.064 (1)0.035 (1)0.035 (1)0.006 (1)0.006 (1)0.017 (1)
N10.027 (1)0.029 (1)0.029 (1)0.004 (1)0.004 (1)0.013 (1)
N20.029 (1)0.028 (1)0.028 (1)0.006 (1)0.007 (1)0.012 (1)
C10.021 (1)0.029 (1)0.026 (1)0.002 (1)0.001 (1)0.014 (1)
C20.033 (1)0.029 (1)0.027 (1)0.006 (1)0.007 (1)0.011 (1)
C30.043 (1)0.029 (1)0.040 (1)0.008 (1)0.011 (1)0.018 (1)
C40.044 (1)0.042 (1)0.035 (1)0.007 (1)0.007 (1)0.025 (1)
C50.038 (1)0.043 (1)0.024 (1)0.000 (1)0.001 (1)0.013 (1)
C60.031 (1)0.027 (1)0.027 (1)0.002 (1)0.001 (1)0.011 (1)
C70.023 (1)0.028 (1)0.024 (1)0.004 (1)0.003 (1)0.011 (1)
C80.034 (1)0.032 (1)0.032 (1)0.000 (1)0.003 (1)0.016 (1)
C90.032 (1)0.041 (1)0.032 (1)0.007 (1)0.001 (1)0.006 (1)
C100.033 (1)0.056 (2)0.029 (1)0.005 (1)0.004 (1)0.013 (1)
C110.051 (2)0.045 (2)0.045 (1)0.008 (1)0.011 (1)0.023 (1)
C120.046 (1)0.031 (1)0.039 (1)0.003 (1)0.008 (1)0.014 (1)
C130.027 (1)0.021 (1)0.033 (1)0.003 (1)0.003 (1)0.007 (1)
C140.035 (1)0.029 (1)0.040 (1)0.001 (1)0.005 (1)0.013 (1)
C150.046 (2)0.042 (2)0.069 (2)0.005 (1)0.019 (1)0.024 (1)
C160.030 (1)0.040 (2)0.091 (2)0.010 (1)0.001 (1)0.015 (2)
C170.033 (1)0.046 (2)0.064 (2)0.003 (1)0.013 (1)0.005 (1)
C180.035 (1)0.042 (1)0.039 (1)0.001 (1)0.002 (1)0.010 (1)
C190.024 (1)0.026 (1)0.031 (1)0.000 (1)0.002 (1)0.010 (1)
C200.033 (1)0.027 (1)0.034 (1)0.001 (1)0.000 (1)0.009 (1)
C210.027 (1)0.031 (1)0.023 (1)0.010 (1)0.006 (1)0.010 (1)
C220.028 (1)0.033 (1)0.038 (1)0.004 (1)0.004 (1)0.016 (1)
C230.027 (1)0.035 (1)0.048 (1)0.001 (1)0.003 (1)0.008 (1)
C240.029 (1)0.045 (1)0.033 (1)0.008 (1)0.003 (1)0.004 (1)
C250.032 (1)0.040 (1)0.024 (1)0.012 (1)0.005 (1)0.008 (1)
C260.049 (2)0.056 (2)0.024 (1)0.019 (1)0.000 (1)0.016 (1)
C270.058 (2)0.057 (2)0.030 (1)0.020 (1)0.010 (1)0.028 (1)
C280.046 (1)0.038 (1)0.031 (1)0.015 (1)0.015 (1)0.020 (1)
C290.065 (2)0.040 (1)0.047 (2)0.015 (1)0.024 (1)0.029 (1)
C300.052 (2)0.034 (1)0.058 (2)0.003 (1)0.023 (1)0.022 (1)
C310.038 (1)0.029 (1)0.043 (1)0.002 (1)0.011 (1)0.013 (1)
C320.032 (1)0.030 (1)0.025 (1)0.011 (1)0.010 (1)0.012 (1)
Geometric parameters (Å, º) top
Sn1—C12.125 (2)C22—C231.406 (3)
Sn1—C72.126 (2)C23—C241.364 (4)
Sn1—C132.130 (2)C24—C251.400 (3)
Sn1—O12.208 (1)C25—C261.430 (3)
Sn1—O1w2.308 (1)C26—C271.340 (4)
Cl1—C201.763 (2)C27—C281.429 (4)
Cl2—C201.755 (2)C28—C291.406 (4)
Cl3—C201.756 (2)C28—C321.413 (3)
O1—C191.274 (3)C29—C301.363 (4)
O2—C191.201 (3)C30—C311.391 (4)
N1—C221.324 (3)O1w—H1w10.89 (2)
N1—C211.358 (3)O1w—H1w20.88 (2)
N2—C311.323 (3)C2—H20.95
N2—C321.354 (3)C3—H30.95
C1—C21.395 (3)C4—H40.95
C1—C61.401 (3)C5—H50.95
C2—C31.381 (3)C6—H60.95
C3—C41.387 (3)C8—H80.95
C4—C51.386 (3)C9—H90.95
C5—C61.377 (3)C10—H100.95
C7—C121.393 (3)C11—H110.95
C7—C81.394 (3)C12—H120.95
C8—C91.380 (3)C14—H140.95
C9—C101.383 (4)C15—H150.95
C10—C111.378 (4)C16—H160.95
C11—C121.385 (3)C17—H170.95
C13—C141.383 (3)C18—H180.95
C13—C181.394 (3)C22—H220.95
C14—C151.387 (3)C23—H230.95
C15—C161.375 (4)C24—H240.95
C16—C171.365 (4)C26—H260.95
C17—C181.389 (4)C27—H270.95
C19—C201.567 (3)C29—H290.95
C21—C251.412 (3)C30—H300.95
C21—C321.442 (3)C31—H310.95
C1—Sn1—C7122.2 (1)C29—C28—C27123.4 (2)
C1—Sn1—C13115.5 (1)C32—C28—C27119.0 (2)
C1—Sn1—O187.3 (1)C30—C29—C28120.2 (2)
C1—Sn1—O1w87.2 (1)C29—C30—C31118.1 (2)
C7—Sn1—C13121.8 (1)N2—C31—C30124.0 (2)
C7—Sn1—O197.4 (1)N2—C32—C28121.5 (2)
C7—Sn1—O1w85.7 (1)N2—C32—C21119.2 (2)
C13—Sn1—O191.7 (1)C28—C32—C21119.3 (2)
C13—Sn1—O1w90.4 (1)Sn1—O1w—H1w1120 (2)
O1—Sn1—O1w174.5 (1)Sn1—O1w—H1w2121 (2)
C19—O1—Sn1123.7 (1)H1w1—O1w—H1w2110 (2)
C22—N1—C21118.0 (2)C3—C2—H2119.5
C31—N2—C32118.4 (2)C1—C2—H2119.5
C2—C1—C6118.4 (2)C2—C3—H3120.1
C2—C1—Sn1121.0 (2)C4—C3—H3120.1
C6—C1—Sn1120.7 (2)C3—C4—H4120.0
C3—C2—C1121.1 (2)C5—C4—H4120.0
C2—C3—C4119.7 (2)C6—C5—H5119.8
C3—C4—C5119.9 (2)C4—C5—H5119.8
C6—C5—C4120.3 (2)C5—C6—H6119.7
C5—C6—C1120.5 (2)C1—C6—H6119.7
C12—C7—C8118.1 (2)C9—C8—H8119.3
C12—C7—Sn1121.6 (2)C7—C8—H8119.3
C8—C7—Sn1120.3 (2)C10—C9—H9120.1
C9—C8—C7121.4 (2)C8—C9—H9120.1
C10—C9—C8119.8 (2)C11—C10—H10120.2
C11—C10—C9119.6 (2)C9—C10—H10120.2
C10—C11—C12120.7 (2)C10—C11—H11119.6
C11—C12—C7120.3 (2)C12—C11—H11119.6
C14—C13—C18118.0 (2)C11—C12—H12119.8
C14—C13—Sn1122.4 (2)C7—C12—H12119.8
C18—C13—Sn1119.5 (2)C13—C14—H14119.6
C13—C14—C15120.8 (2)C15—C14—H14119.6
C16—C15—C14120.4 (3)C16—C15—H15119.8
C17—C16—C15119.6 (2)C14—C15—H15119.8
C16—C17—C18120.5 (3)C17—C16—H16120.2
C13—C18—C17120.6 (3)C15—C16—H16120.2
O2—C19—O1128.9 (2)C16—C17—H17119.8
O2—C19—C20118.0 (2)C18—C17—H17119.8
O1—C19—C20113.0 (2)C13—C18—H18119.7
C19—C20—Cl3110.7 (2)C17—C18—H18119.7
C19—C20—Cl2107.8 (2)N1—C22—H22117.9
Cl3—C20—Cl2109.9 (1)C23—C22—H22117.9
C19—C20—Cl1111.9 (2)C24—C23—H23121.0
Cl3—C20—Cl1107.7 (1)C22—C23—H23121.0
Cl2—C20—Cl1108.9 (1)C23—C24—H24120.1
N1—C21—C25121.6 (2)C25—C24—H24120.1
N1—C21—C32118.8 (2)C27—C26—H26119.3
C25—C21—C32119.6 (2)C25—C26—H26119.3
N1—C22—C23124.1 (2)C26—C27—H27119.2
C24—C23—C22118.0 (2)C28—C27—H27119.2
C23—C24—C25119.8 (2)C30—C29—H29119.9
C24—C25—C21118.4 (2)C28—C29—H29119.9
C24—C25—C26122.7 (2)C29—C30—H30121.0
C21—C25—C26118.9 (2)C31—C30—H30121.0
C27—C26—C25121.5 (2)N2—C31—H31118.0
C26—C27—C28121.5 (2)C30—C31—H31118.0
C29—C28—C32117.6 (2)
C1—Sn1—O1—C19163.8 (2)C13—C14—C15—C160.8 (4)
C7—Sn1—O1—C1974.0 (2)C14—C15—C16—C170.7 (4)
C13—Sn1—O1—C1948.4 (2)C15—C16—C17—C181.0 (4)
O1w—Sn1—O1—C19161.0 (5)C14—C13—C18—C171.5 (3)
C7—Sn1—C1—C258.6 (2)Sn1—C13—C18—C17174.3 (2)
C13—Sn1—C1—C2113.7 (2)C16—C17—C18—C130.1 (4)
O1—Sn1—C1—C2155.7 (2)Sn1—O1—C19—O222.7 (3)
O1w—Sn1—C1—C224.6 (2)Sn1—O1—C19—C20154.4 (1)
C7—Sn1—C1—C6123.1 (2)O2—C19—C20—Cl327.3 (3)
C13—Sn1—C1—C664.7 (2)O1—C19—C20—Cl3155.3 (2)
O1—Sn1—C1—C626.0 (2)O2—C19—C20—Cl292.8 (2)
O1w—Sn1—C1—C6153.8 (2)O1—C19—C20—Cl284.6 (2)
C6—C1—C2—C30.8 (3)O2—C19—C20—Cl1147.5 (2)
Sn1—C1—C2—C3177.6 (2)O1—C19—C20—Cl135.1 (2)
C1—C2—C3—C40.1 (3)C22—N1—C21—C253.0 (3)
C2—C3—C4—C50.7 (4)C22—N1—C21—C32178.2 (2)
C3—C4—C5—C60.7 (4)C21—N1—C22—C231.0 (3)
C4—C5—C6—C10.1 (3)N1—C22—C23—C240.9 (3)
C2—C1—C6—C50.8 (3)C22—C23—C24—C250.9 (3)
Sn1—C1—C6—C5177.6 (2)C23—C24—C25—C210.9 (3)
C1—Sn1—C7—C12146.6 (2)C23—C24—C25—C26179.9 (2)
C13—Sn1—C7—C1241.6 (2)N1—C21—C25—C242.9 (3)
O1—Sn1—C7—C1255.1 (2)C32—C21—C25—C24178.2 (2)
O1w—Sn1—C7—C12129.5 (2)N1—C21—C25—C26178.1 (2)
C1—Sn1—C7—C835.3 (2)C32—C21—C25—C260.8 (3)
C13—Sn1—C7—C8136.5 (2)C24—C25—C26—C27179.3 (2)
O1—Sn1—C7—C8126.8 (2)C21—C25—C26—C271.7 (3)
O1w—Sn1—C7—C848.7 (2)C25—C26—C27—C280.9 (4)
C12—C7—C8—C90.2 (3)C26—C27—C28—C29177.2 (2)
Sn1—C7—C8—C9178.5 (2)C26—C27—C28—C322.4 (4)
C7—C8—C9—C100.7 (4)C32—C28—C29—C301.6 (3)
C8—C9—C10—C110.3 (4)C27—C28—C29—C30178.8 (2)
C9—C10—C11—C120.5 (4)C28—C29—C30—C311.8 (4)
C10—C11—C12—C71.0 (4)C32—N2—C31—C301.8 (3)
C8—C7—C12—C110.6 (4)C29—C30—C31—N21.8 (4)
Sn1—C7—C12—C11177.6 (2)C31—N2—C32—C285.4 (3)
C1—Sn1—C13—C14159.5 (2)C31—N2—C32—C21174.7 (2)
C7—Sn1—C13—C1412.9 (2)C29—C28—C32—N25.3 (3)
O1—Sn1—C13—C14112.7 (2)C27—C28—C32—N2175.1 (2)
O1w—Sn1—C13—C1472.4 (2)C29—C28—C32—C21174.8 (2)
C1—Sn1—C13—C1816.1 (2)C27—C28—C32—C214.8 (3)
C7—Sn1—C13—C18171.6 (2)N1—C21—C32—N25.2 (3)
O1—Sn1—C13—C1871.8 (2)C25—C21—C32—N2175.9 (2)
O1w—Sn1—C13—C18103.2 (2)N1—C21—C32—C28174.9 (2)
C18—C13—C14—C151.8 (3)C25—C21—C32—C284.0 (3)
Sn1—C13—C14—C15173.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1w—H1w1···N10.89 (2)1.89 (2)2.758 (2)166 (2)
O1w—H1w2···N2i0.88 (2)1.89 (2)2.755 (2)167 (2)
Symmetry code: (i) x+1, y+1, z+1.
 

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