metal-organic compounds
Low-temperature redetermination of aquachloridotriphenyltin(IV)–1,10-phenanthroline (1/1)
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
The 6H5)3Cl(H2O)]·C12H8N2, which was refined in the triclinic P [Fu, Gao, Ma & Zhang (2005). Chin. J. Synth. Chem. 13, 55–57], has been redetermined in the monoclinic C2/c from low-temperature diffraction measurements. The Sn atom is five-coordinate in a trans-C3SnClO trigonal-bipyramidal geometry; the coordinated water molecule forms a pair of hydrogen bonds to the nitrogen heterocycle.
of the title compound, [Sn(CRelated literature
For a description of the title compound in the triclinic P, see: Fu et al. (2005). Aquachloridotri(p-chlorophenyl)tin.1,10-phenanthroline exists as a hydrogen-bonded dinuclear compound, see: Ng & Kumar Das (1996). This study also mentions the existence of a monoclinic P21/c modification of the title compound. This modification is, in fact, commensurately modulated; see: Rae et al. (2005).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; 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, 2008).
Supporting information
10.1107/S1600536808024343/tk2288sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808024343/tk2288Isup2.hkl
Triphenyltin chloride (0.39 g, 1 mmol) and 1,10-phenanthroline monohydrate (0.20 g, 1 mmol) were dissolved in hot ethanol (10 ml). Crystals of the compound separated after a day.
The carbon-bound hydrogen atoms were placed at calculated positions with C—H = 0.95 Å, and with U(H) = 1.2Ueq(C). The water H-atoms were refined with a distance restraint of O—H 0.84±0.01 Å.
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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, 2008).[Sn(C6H5)3Cl(H2O)]·C12H8N2 | F(000) = 2352 |
Mr = 583.66 | Dx = 1.541 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 9047 reflections |
a = 16.3739 (2) Å | θ = 2.3–28.3° |
b = 17.3120 (2) Å | µ = 1.15 mm−1 |
c = 18.4295 (2) Å | T = 100 K |
β = 105.602 (1)° | Block, colorless |
V = 5031.6 (1) Å3 | 0.30 × 0.20 × 0.10 mm |
Z = 8 |
Bruker SMART APEX diffractometer | 5746 independent reflections |
Radiation source: fine-focus sealed tube | 5333 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
ω scans | θmax = 27.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −21→21 |
Tmin = 0.768, Tmax = 0.894 | k = −22→22 |
23117 measured reflections | l = −22→23 |
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)] = 0.020 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0231P)2 + 10.9613P] where P = (Fo2 + 2Fc2)/3 |
5746 reflections | (Δ/σ)max = 0.001 |
324 parameters | Δρmax = 0.72 e Å−3 |
2 restraints | Δρmin = −0.60 e Å−3 |
[Sn(C6H5)3Cl(H2O)]·C12H8N2 | V = 5031.6 (1) Å3 |
Mr = 583.66 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 16.3739 (2) Å | µ = 1.15 mm−1 |
b = 17.3120 (2) Å | T = 100 K |
c = 18.4295 (2) Å | 0.30 × 0.20 × 0.10 mm |
β = 105.602 (1)° |
Bruker SMART APEX diffractometer | 5746 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 5333 reflections with I > 2σ(I) |
Tmin = 0.768, Tmax = 0.894 | Rint = 0.015 |
23117 measured reflections |
R[F2 > 2σ(F2)] = 0.020 | 2 restraints |
wR(F2) = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0231P)2 + 10.9613P] where P = (Fo2 + 2Fc2)/3 |
5746 reflections | Δρmax = 0.72 e Å−3 |
324 parameters | Δρmin = −0.60 e Å−3 |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.283489 (7) | 0.505787 (6) | 0.562615 (6) | 0.01482 (4) | |
Cl1 | 0.18859 (3) | 0.44885 (2) | 0.44433 (2) | 0.02027 (8) | |
O1 | 0.37284 (8) | 0.56254 (7) | 0.67064 (7) | 0.0195 (2) | |
H1O | 0.3578 (17) | 0.6082 (8) | 0.6762 (16) | 0.050 (8)* | |
H2O | 0.4223 (9) | 0.5695 (16) | 0.6674 (16) | 0.053 (8)* | |
N1 | 0.36099 (9) | 0.71863 (8) | 0.67875 (8) | 0.0188 (3) | |
N2 | 0.50883 (9) | 0.65084 (9) | 0.65883 (8) | 0.0216 (3) | |
C1 | 0.34419 (10) | 0.58146 (9) | 0.50254 (9) | 0.0172 (3) | |
C2 | 0.40237 (12) | 0.55391 (11) | 0.46606 (11) | 0.0264 (4) | |
H2 | 0.4115 | 0.4999 | 0.4636 | 0.032* | |
C3 | 0.44752 (13) | 0.60528 (14) | 0.43296 (12) | 0.0343 (5) | |
H3 | 0.4872 | 0.5861 | 0.4081 | 0.041* | |
C4 | 0.43462 (13) | 0.68404 (13) | 0.43620 (12) | 0.0330 (5) | |
H4 | 0.4662 | 0.7189 | 0.4146 | 0.040* | |
C5 | 0.37588 (13) | 0.71172 (11) | 0.47086 (11) | 0.0287 (4) | |
H5 | 0.3662 | 0.7657 | 0.4723 | 0.034* | |
C6 | 0.33064 (12) | 0.66094 (10) | 0.50385 (10) | 0.0214 (3) | |
H6 | 0.2901 | 0.6806 | 0.5275 | 0.026* | |
C7 | 0.33380 (10) | 0.39676 (9) | 0.60801 (10) | 0.0179 (3) | |
C8 | 0.36605 (13) | 0.38717 (11) | 0.68536 (11) | 0.0274 (4) | |
H8 | 0.3716 | 0.4306 | 0.7178 | 0.033* | |
C9 | 0.39024 (15) | 0.31425 (13) | 0.71554 (13) | 0.0366 (5) | |
H9 | 0.4120 | 0.3082 | 0.7685 | 0.044* | |
C10 | 0.38270 (13) | 0.25093 (11) | 0.66890 (13) | 0.0331 (5) | |
H10 | 0.3982 | 0.2012 | 0.6898 | 0.040* | |
C11 | 0.35274 (12) | 0.25958 (10) | 0.59211 (13) | 0.0292 (4) | |
H11 | 0.3493 | 0.2161 | 0.5600 | 0.035* | |
C12 | 0.32755 (11) | 0.33198 (10) | 0.56158 (11) | 0.0218 (3) | |
H12 | 0.3059 | 0.3375 | 0.5086 | 0.026* | |
C13 | 0.18329 (10) | 0.54725 (9) | 0.60574 (10) | 0.0178 (3) | |
C14 | 0.19228 (12) | 0.54833 (10) | 0.68337 (10) | 0.0217 (3) | |
H14 | 0.2444 | 0.5327 | 0.7171 | 0.026* | |
C15 | 0.12560 (13) | 0.57213 (10) | 0.71168 (11) | 0.0264 (4) | |
H15 | 0.1321 | 0.5724 | 0.7645 | 0.032* | |
C16 | 0.04974 (13) | 0.59533 (11) | 0.66251 (12) | 0.0292 (4) | |
H16 | 0.0043 | 0.6117 | 0.6818 | 0.035* | |
C17 | 0.03984 (12) | 0.59478 (11) | 0.58568 (12) | 0.0281 (4) | |
H17 | −0.0122 | 0.6110 | 0.5522 | 0.034* | |
C18 | 0.10621 (11) | 0.57037 (10) | 0.55742 (11) | 0.0222 (3) | |
H18 | 0.0989 | 0.5694 | 0.5045 | 0.027* | |
C19 | 0.29276 (11) | 0.75240 (11) | 0.68954 (10) | 0.0226 (4) | |
H19 | 0.2498 | 0.7204 | 0.6994 | 0.027* | |
C20 | 0.27997 (12) | 0.83268 (11) | 0.68733 (11) | 0.0273 (4) | |
H20 | 0.2301 | 0.8543 | 0.6959 | 0.033* | |
C21 | 0.34104 (13) | 0.87859 (11) | 0.67250 (11) | 0.0282 (4) | |
H21 | 0.3340 | 0.9331 | 0.6704 | 0.034* | |
C22 | 0.41470 (12) | 0.84523 (10) | 0.66025 (10) | 0.0234 (4) | |
C23 | 0.42300 (11) | 0.76392 (10) | 0.66440 (9) | 0.0184 (3) | |
C24 | 0.47983 (13) | 0.89168 (11) | 0.64384 (11) | 0.0300 (4) | |
H24 | 0.4737 | 0.9463 | 0.6413 | 0.036* | |
C25 | 0.54943 (13) | 0.85914 (12) | 0.63203 (11) | 0.0309 (4) | |
H25 | 0.5915 | 0.8910 | 0.6206 | 0.037* | |
C26 | 0.56146 (12) | 0.77707 (12) | 0.63629 (10) | 0.0257 (4) | |
C27 | 0.49893 (11) | 0.72867 (10) | 0.65276 (9) | 0.0201 (3) | |
C28 | 0.63516 (12) | 0.74201 (14) | 0.62609 (11) | 0.0326 (5) | |
H28 | 0.6781 | 0.7727 | 0.6145 | 0.039* | |
C29 | 0.64472 (13) | 0.66405 (14) | 0.63288 (11) | 0.0346 (5) | |
H29 | 0.6942 | 0.6395 | 0.6265 | 0.042* | |
C30 | 0.57960 (12) | 0.62074 (12) | 0.64960 (11) | 0.0283 (4) | |
H30 | 0.5868 | 0.5664 | 0.6546 | 0.034* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.01639 (6) | 0.01177 (6) | 0.01746 (6) | −0.00055 (4) | 0.00652 (4) | −0.00002 (4) |
Cl1 | 0.02075 (19) | 0.01617 (18) | 0.0221 (2) | −0.00109 (14) | 0.00273 (15) | −0.00226 (14) |
O1 | 0.0198 (6) | 0.0156 (6) | 0.0235 (6) | −0.0023 (5) | 0.0066 (5) | −0.0015 (5) |
N1 | 0.0187 (7) | 0.0197 (7) | 0.0170 (7) | −0.0021 (5) | 0.0033 (6) | −0.0004 (5) |
N2 | 0.0213 (7) | 0.0260 (7) | 0.0176 (7) | 0.0007 (6) | 0.0051 (6) | −0.0019 (6) |
C1 | 0.0168 (8) | 0.0183 (8) | 0.0160 (8) | −0.0034 (6) | 0.0033 (6) | 0.0001 (6) |
C2 | 0.0241 (9) | 0.0281 (9) | 0.0296 (10) | 0.0026 (7) | 0.0118 (8) | 0.0030 (7) |
C3 | 0.0222 (9) | 0.0508 (13) | 0.0341 (11) | −0.0009 (9) | 0.0152 (8) | 0.0082 (9) |
C4 | 0.0270 (10) | 0.0426 (11) | 0.0272 (10) | −0.0153 (9) | 0.0035 (8) | 0.0114 (9) |
C5 | 0.0363 (11) | 0.0216 (9) | 0.0234 (9) | −0.0116 (8) | −0.0002 (8) | 0.0035 (7) |
C6 | 0.0264 (9) | 0.0188 (8) | 0.0183 (8) | −0.0031 (7) | 0.0046 (7) | −0.0003 (6) |
C7 | 0.0151 (7) | 0.0169 (7) | 0.0240 (9) | 0.0004 (6) | 0.0091 (6) | 0.0027 (6) |
C8 | 0.0338 (10) | 0.0258 (9) | 0.0240 (9) | 0.0089 (8) | 0.0102 (8) | 0.0037 (7) |
C9 | 0.0460 (13) | 0.0365 (11) | 0.0307 (11) | 0.0169 (10) | 0.0161 (10) | 0.0148 (9) |
C10 | 0.0320 (10) | 0.0213 (9) | 0.0506 (13) | 0.0112 (8) | 0.0190 (10) | 0.0157 (9) |
C11 | 0.0227 (9) | 0.0150 (8) | 0.0517 (13) | 0.0007 (7) | 0.0132 (9) | −0.0005 (8) |
C12 | 0.0180 (8) | 0.0179 (8) | 0.0300 (9) | −0.0011 (6) | 0.0074 (7) | −0.0003 (7) |
C13 | 0.0191 (8) | 0.0112 (7) | 0.0254 (9) | −0.0023 (6) | 0.0102 (7) | −0.0011 (6) |
C14 | 0.0243 (9) | 0.0168 (8) | 0.0260 (9) | −0.0002 (7) | 0.0102 (7) | −0.0006 (6) |
C15 | 0.0363 (10) | 0.0198 (8) | 0.0288 (10) | −0.0002 (7) | 0.0189 (8) | −0.0015 (7) |
C16 | 0.0291 (10) | 0.0226 (9) | 0.0439 (12) | 0.0031 (7) | 0.0235 (9) | 0.0005 (8) |
C17 | 0.0209 (9) | 0.0248 (9) | 0.0403 (11) | 0.0038 (7) | 0.0114 (8) | 0.0035 (8) |
C18 | 0.0232 (9) | 0.0188 (8) | 0.0264 (9) | 0.0005 (6) | 0.0095 (7) | 0.0018 (7) |
C19 | 0.0197 (8) | 0.0270 (9) | 0.0196 (9) | 0.0000 (7) | 0.0028 (7) | −0.0005 (7) |
C20 | 0.0246 (9) | 0.0276 (9) | 0.0267 (10) | 0.0069 (7) | 0.0019 (8) | −0.0024 (7) |
C21 | 0.0341 (10) | 0.0200 (8) | 0.0242 (9) | 0.0044 (7) | −0.0030 (8) | −0.0001 (7) |
C22 | 0.0275 (9) | 0.0213 (8) | 0.0168 (8) | −0.0039 (7) | −0.0018 (7) | 0.0010 (6) |
C23 | 0.0205 (8) | 0.0196 (8) | 0.0126 (7) | −0.0029 (6) | 0.0002 (6) | 0.0000 (6) |
C24 | 0.0372 (11) | 0.0223 (9) | 0.0245 (10) | −0.0112 (8) | −0.0018 (8) | 0.0049 (7) |
C25 | 0.0312 (10) | 0.0364 (11) | 0.0219 (9) | −0.0183 (8) | 0.0015 (8) | 0.0057 (8) |
C26 | 0.0227 (9) | 0.0377 (10) | 0.0154 (8) | −0.0088 (8) | 0.0032 (7) | 0.0010 (7) |
C27 | 0.0200 (8) | 0.0261 (8) | 0.0134 (8) | −0.0048 (7) | 0.0027 (6) | −0.0005 (6) |
C28 | 0.0231 (9) | 0.0547 (13) | 0.0214 (9) | −0.0102 (9) | 0.0082 (8) | −0.0015 (9) |
C29 | 0.0236 (9) | 0.0586 (14) | 0.0239 (10) | 0.0023 (9) | 0.0104 (8) | −0.0066 (9) |
C30 | 0.0279 (10) | 0.0360 (10) | 0.0211 (9) | 0.0032 (8) | 0.0068 (8) | −0.0055 (8) |
Sn1—C1 | 2.127 (2) | C12—H12 | 0.9500 |
Sn1—C7 | 2.138 (2) | C13—C18 | 1.393 (2) |
Sn1—C13 | 2.131 (2) | C13—C14 | 1.398 (2) |
Sn1—O1 | 2.346 (1) | C14—C15 | 1.393 (2) |
Sn1—Cl1 | 2.5132 (4) | C14—H14 | 0.9500 |
O1—H1O | 0.84 (1) | C15—C16 | 1.386 (3) |
O1—H2O | 0.84 (1) | C15—H15 | 0.9500 |
N1—C19 | 1.322 (2) | C16—C17 | 1.381 (3) |
N1—C23 | 1.364 (2) | C16—H16 | 0.9500 |
N2—C30 | 1.323 (2) | C17—C18 | 1.391 (2) |
N2—C27 | 1.358 (2) | C17—H17 | 0.9500 |
C1—C6 | 1.395 (2) | C18—H18 | 0.9500 |
C1—C2 | 1.390 (2) | C19—C20 | 1.405 (3) |
C2—C3 | 1.397 (3) | C19—H19 | 0.9500 |
C2—H2 | 0.9500 | C20—C21 | 1.361 (3) |
C3—C4 | 1.384 (3) | C20—H20 | 0.9500 |
C3—H3 | 0.9500 | C21—C22 | 1.409 (3) |
C4—C5 | 1.376 (3) | C21—H21 | 0.9500 |
C4—H4 | 0.9500 | C22—C23 | 1.414 (2) |
C5—C6 | 1.390 (2) | C22—C24 | 1.432 (3) |
C5—H5 | 0.9500 | C23—C27 | 1.452 (2) |
C6—H6 | 0.9500 | C24—C25 | 1.340 (3) |
C7—C12 | 1.398 (2) | C24—H24 | 0.9500 |
C7—C8 | 1.391 (3) | C25—C26 | 1.434 (3) |
C8—C9 | 1.393 (3) | C25—H25 | 0.9500 |
C8—H8 | 0.9500 | C26—C28 | 1.408 (3) |
C9—C10 | 1.378 (3) | C26—C27 | 1.418 (2) |
C9—H9 | 0.9500 | C28—C29 | 1.361 (3) |
C10—C11 | 1.376 (3) | C28—H28 | 0.9500 |
C10—H10 | 0.9500 | C29—C30 | 1.404 (3) |
C11—C12 | 1.390 (2) | C29—H29 | 0.9500 |
C11—H11 | 0.9500 | C30—H30 | 0.9500 |
C1—Sn1—C7 | 124.25 (6) | C14—C13—Sn1 | 120.42 (13) |
C1—Sn1—C13 | 120.08 (6) | C13—C14—C15 | 120.64 (18) |
C1—Sn1—O1 | 84.93 (5) | C13—C14—H14 | 119.7 |
C1—Sn1—Cl1 | 93.24 (5) | C15—C14—H14 | 119.7 |
C7—Sn1—C13 | 113.94 (6) | C16—C15—C14 | 119.73 (18) |
C7—Sn1—Cl1 | 94.38 (5) | C16—C15—H15 | 120.1 |
C7—Sn1—O1 | 87.19 (6) | C14—C15—H15 | 120.1 |
C13—Sn1—O1 | 84.80 (6) | C15—C16—C17 | 120.38 (17) |
C13—Sn1—Cl1 | 95.58 (5) | C15—C16—H16 | 119.8 |
O1—Sn1—Cl1 | 178.06 (3) | C17—C16—H16 | 119.8 |
Sn1—O1—H1o | 111.1 (19) | C16—C17—C18 | 119.86 (18) |
Sn1—O1—H2o | 113 (2) | C16—C17—H17 | 120.1 |
H1o—O1—H2o | 101 (3) | C18—C17—H17 | 120.1 |
C19—N1—C23 | 118.57 (15) | C17—C18—C13 | 120.82 (18) |
C30—N2—C27 | 118.00 (16) | C17—C18—H18 | 119.6 |
C6—C1—C2 | 118.67 (16) | C13—C18—H18 | 119.6 |
C6—C1—Sn1 | 119.99 (12) | N1—C19—C20 | 123.95 (17) |
C2—C1—Sn1 | 121.17 (13) | N1—C19—H19 | 118.0 |
C1—C2—C3 | 120.32 (18) | C20—C19—H19 | 118.0 |
C1—C2—H2 | 119.8 | C21—C20—C19 | 118.14 (17) |
C3—C2—H2 | 119.8 | C21—C20—H20 | 120.9 |
C4—C3—C2 | 120.23 (19) | C19—C20—H20 | 120.9 |
C4—C3—H3 | 119.9 | C20—C21—C22 | 119.97 (17) |
C2—C3—H3 | 119.9 | C20—C21—H21 | 120.0 |
C5—C4—C3 | 119.82 (17) | C22—C21—H21 | 120.0 |
C5—C4—H4 | 120.1 | C23—C22—C21 | 118.24 (17) |
C3—C4—H4 | 120.1 | C23—C22—C24 | 120.29 (18) |
C4—C5—C6 | 120.27 (18) | C21—C22—C24 | 121.47 (17) |
C4—C5—H5 | 119.9 | N1—C23—C22 | 121.12 (16) |
C6—C5—H5 | 119.9 | N1—C23—C27 | 119.92 (15) |
C5—C6—C1 | 120.67 (17) | C22—C23—C27 | 118.95 (16) |
C5—C6—H6 | 119.7 | C25—C24—C22 | 120.82 (18) |
C1—C6—H6 | 119.7 | C25—C24—H24 | 119.6 |
C12—C7—C8 | 118.48 (16) | C22—C24—H24 | 119.6 |
C12—C7—Sn1 | 120.79 (13) | C24—C25—C26 | 121.20 (17) |
C8—C7—Sn1 | 120.45 (13) | C24—C25—H25 | 119.4 |
C9—C8—C7 | 120.42 (19) | C26—C25—H25 | 119.4 |
C9—C8—H8 | 119.8 | C28—C26—C27 | 117.91 (18) |
C7—C8—H8 | 119.8 | C28—C26—C25 | 122.01 (18) |
C10—C9—C8 | 120.2 (2) | C27—C26—C25 | 120.06 (18) |
C10—C9—H9 | 119.9 | N2—C27—C26 | 121.80 (17) |
C8—C9—H9 | 119.9 | N2—C27—C23 | 119.53 (15) |
C11—C10—C9 | 120.17 (18) | C26—C27—C23 | 118.66 (16) |
C11—C10—H10 | 119.9 | C29—C28—C26 | 119.80 (18) |
C9—C10—H10 | 119.9 | C29—C28—H28 | 120.1 |
C10—C11—C12 | 119.95 (18) | C26—C28—H28 | 120.1 |
C10—C11—H11 | 120.0 | C28—C29—C30 | 118.33 (19) |
C12—C11—H11 | 120.0 | C28—C29—H29 | 120.8 |
C11—C12—C7 | 120.72 (18) | C30—C29—H29 | 120.8 |
C11—C12—H12 | 119.6 | N2—C30—C29 | 124.1 (2) |
C7—C12—H12 | 119.6 | N2—C30—H30 | 117.9 |
C18—C13—C14 | 118.56 (16) | C29—C30—H30 | 117.9 |
C18—C13—Sn1 | 120.95 (13) | ||
C13—Sn1—C1—C6 | 12.62 (16) | C18—C13—C14—C15 | −0.1 (2) |
C7—Sn1—C1—C6 | −151.49 (13) | Sn1—C13—C14—C15 | −177.11 (13) |
O1—Sn1—C1—C6 | −68.37 (14) | C13—C14—C15—C16 | −0.3 (3) |
Cl1—Sn1—C1—C6 | 110.98 (13) | C14—C15—C16—C17 | 0.2 (3) |
C13—Sn1—C1—C2 | −172.10 (14) | C15—C16—C17—C18 | 0.4 (3) |
C7—Sn1—C1—C2 | 23.79 (17) | C16—C17—C18—C13 | −0.8 (3) |
O1—Sn1—C1—C2 | 106.90 (15) | C14—C13—C18—C17 | 0.7 (3) |
Cl1—Sn1—C1—C2 | −73.75 (14) | Sn1—C13—C18—C17 | 177.66 (13) |
C6—C1—C2—C3 | 1.4 (3) | C23—N1—C19—C20 | −0.2 (3) |
Sn1—C1—C2—C3 | −173.93 (15) | N1—C19—C20—C21 | 0.6 (3) |
C1—C2—C3—C4 | 0.0 (3) | C19—C20—C21—C22 | −0.3 (3) |
C2—C3—C4—C5 | −1.3 (3) | C20—C21—C22—C23 | −0.4 (3) |
C3—C4—C5—C6 | 1.2 (3) | C20—C21—C22—C24 | 179.42 (18) |
C4—C5—C6—C1 | 0.2 (3) | C19—N1—C23—C22 | −0.6 (2) |
C2—C1—C6—C5 | −1.5 (3) | C19—N1—C23—C27 | 179.62 (15) |
Sn1—C1—C6—C5 | 173.91 (13) | C21—C22—C23—N1 | 0.9 (3) |
C1—Sn1—C7—C12 | −78.22 (15) | C24—C22—C23—N1 | −178.92 (16) |
C13—Sn1—C7—C12 | 116.81 (13) | C21—C22—C23—C27 | −179.32 (16) |
O1—Sn1—C7—C12 | −160.15 (13) | C24—C22—C23—C27 | 0.8 (3) |
Cl1—Sn1—C7—C12 | 18.72 (13) | C23—C22—C24—C25 | 0.1 (3) |
C1—Sn1—C7—C8 | 108.01 (14) | C21—C22—C24—C25 | −179.75 (18) |
C13—Sn1—C7—C8 | −56.97 (16) | C22—C24—C25—C26 | −0.7 (3) |
O1—Sn1—C7—C8 | 26.08 (14) | C24—C25—C26—C28 | −178.24 (19) |
Cl1—Sn1—C7—C8 | −155.05 (14) | C24—C25—C26—C27 | 0.4 (3) |
C12—C7—C8—C9 | −1.0 (3) | C30—N2—C27—C26 | 0.6 (3) |
Sn1—C7—C8—C9 | 172.95 (15) | C30—N2—C27—C23 | −178.48 (16) |
C7—C8—C9—C10 | 0.2 (3) | C28—C26—C27—N2 | 0.1 (3) |
C8—C9—C10—C11 | 1.2 (3) | C25—C26—C27—N2 | −178.60 (17) |
C9—C10—C11—C12 | −2.0 (3) | C28—C26—C27—C23 | 179.23 (16) |
C10—C11—C12—C7 | 1.2 (3) | C25—C26—C27—C23 | 0.5 (3) |
C8—C7—C12—C11 | 0.2 (3) | N1—C23—C27—N2 | −2.2 (2) |
Sn1—C7—C12—C11 | −173.66 (13) | C22—C23—C27—N2 | 178.03 (16) |
C1—Sn1—C13—C18 | 66.35 (15) | N1—C23—C27—C26 | 178.62 (16) |
C7—Sn1—C13—C18 | −127.99 (13) | C22—C23—C27—C26 | −1.1 (2) |
O1—Sn1—C13—C18 | 147.42 (13) | C27—C26—C28—C29 | −0.6 (3) |
Cl1—Sn1—C13—C18 | −30.67 (13) | C25—C26—C28—C29 | 178.06 (19) |
C1—Sn1—C13—C14 | −116.71 (13) | C26—C28—C29—C30 | 0.4 (3) |
C7—Sn1—C13—C14 | 48.95 (15) | C27—N2—C30—C29 | −0.9 (3) |
O1—Sn1—C13—C14 | −35.64 (13) | C28—C29—C30—N2 | 0.4 (3) |
Cl1—Sn1—C13—C14 | 146.27 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1o···N1 | 0.84 (1) | 1.91 (1) | 2.716 (2) | 159 (3) |
O1—H2o···N2 | 0.84 (1) | 2.03 (2) | 2.757 (2) | 144 (3) |
Experimental details
Crystal data | |
Chemical formula | [Sn(C6H5)3Cl(H2O)]·C12H8N2 |
Mr | 583.66 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 100 |
a, b, c (Å) | 16.3739 (2), 17.3120 (2), 18.4295 (2) |
β (°) | 105.602 (1) |
V (Å3) | 5031.6 (1) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.15 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEX diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.768, 0.894 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23117, 5746, 5333 |
Rint | 0.015 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.020, 0.052, 1.01 |
No. of reflections | 5746 |
No. of parameters | 324 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
w = 1/[σ2(Fo2) + (0.0231P)2 + 10.9613P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.72, −0.60 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1o···N1 | 0.84 (1) | 1.91 (1) | 2.716 (2) | 159 (3) |
O1—H2o···N2 | 0.84 (1) | 2.03 (2) | 2.757 (2) | 144 (3) |
Acknowledgements
The University of Malaya is thanked for supporting this study through the purchase of the diffractometer.
References
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fu, C.-X., Gao, Z.-H., Ma, C.-L. & Zhang, J.-H. (2005). Chin. J. Synth. Chem. 13, 55–57. CAS Google Scholar
Ng, S. W. & Kumar Das, V. G. (1996). J. Organomet. Chem. 513, 105–108. CAS Google Scholar
Rae, A. D., Haller, K. J. & Ng, S. W. (2005). J. Sci. Technol. Tropics, 1, 157–163. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Interest in aquachlorotriphenyltin.1,10-phenanthroline (Scheme I) involves the existence of a monoclinic P21/c modification [11.960 (1), 12.220 (1), 17.854 (1) Å, β 92.41 (1) °] (Ng & Kumar Das, 1996) that is, in fact, commensurately modulated in P21/n [21.1053 (5), 12.2347 (3), 51.772 (2) Å,101.525 (2) °] (Rae et al., 2005). The compound has the coordinated water molecules of two aquachlorotriphenyltin entities each forming hydrogen bonds to two N-heterocycles. A reported triclinic modification (Fu et al., 2005) has an unit cell [P1: 12.064 (4), 12.075 (4), 18.603 (6) Å, 89.562 (6), 99.567 (5), 72.702 (5) °; V 2672 (5) Å3] that readily transforms to a monoclinic C2/c unit cell. In the correct symmetry, the tin atom is five-coordinate in a trans-C3SnClO trigonal bipyramidal geometry; the coordinated water molecule forms a pair of hydrogen bonds to one N-heterocycle only (Fig. 1, Table 1).