metal-organic compounds
The structure of the title compound, [Sn(C6H5)3(C7H5ClNO2)], contains dimeric units that are stabilized by inter- and intramolecular hydrogen bonds involving amino H atoms and carbonyl O and Cl atoms. The geometry around Sn is slightly distorted tetrahedral and the Sn—C distances are essentially identical.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807005855/om2096sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807005855/om2096Isup2.hkl |
CCDC reference: 640433
Computing details top
Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
(3-Amino-4-chlorobenzoato)triphenyltin(IV) top
Crystal data top
[Sn(C6H5)3(C7H5ClNO2)] | F(000) = 2080 |
Mr = 520.56 | Dx = 1.525 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 100329 reflections |
a = 17.210 (4) Å | θ = 3.2–27.5° |
b = 11.629 (3) Å | µ = 1.27 mm−1 |
c = 23.205 (6) Å | T = 173 K |
β = 102.507 (15)° | Block, colorless |
V = 4534 (2) Å3 | 0.12 × 0.10 × 0.08 mm |
Z = 8 |
Data collection top
Nonius KappaCCD diffractometer | 5184 independent reflections |
Radiation source: fine-focus sealed tube | 3962 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
ω and φ scans | θmax = 27.5°, θmin = 3.2° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −21→22 |
Tmin = 0.863, Tmax = 0.906 | k = −15→14 |
10032 measured reflections | l = −30→30 |
Refinement top
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.082 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.039P)2 + 1.24P] where P = (Fo2 + 2Fc2)/3 |
5184 reflections | (Δ/σ)max < 0.001 |
271 parameters | Δρmax = 0.82 e Å−3 |
0 restraints | Δρmin = −0.65 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.448753 (11) | 0.062848 (16) | 0.109095 (8) | 0.02564 (8) | |
Cl1 | 0.09529 (4) | −0.00277 (7) | −0.21795 (3) | 0.03758 (19) | |
O1 | 0.37334 (12) | 0.06299 (16) | 0.02766 (9) | 0.0340 (5) | |
O2 | 0.32154 (12) | −0.10134 (19) | 0.05186 (9) | 0.0369 (5) | |
N1 | 0.11531 (16) | −0.1997 (2) | −0.13511 (12) | 0.0454 (7) | |
H1A | 0.1179 | −0.2619 | −0.1131 | 0.055* | |
H1B | 0.0828 | −0.1975 | −0.1700 | 0.055* | |
C1 | 0.51260 (16) | 0.2125 (2) | 0.09477 (12) | 0.0263 (6) | |
C2 | 0.59220 (17) | 0.2055 (3) | 0.09055 (12) | 0.0309 (7) | |
H2 | 0.6185 | 0.1322 | 0.0951 | 0.037* | |
C3 | 0.63302 (19) | 0.3029 (3) | 0.07985 (15) | 0.0415 (8) | |
H3 | 0.6876 | 0.2977 | 0.0766 | 0.050* | |
C4 | 0.5956 (2) | 0.4081 (3) | 0.07289 (19) | 0.0542 (11) | |
H4 | 0.6244 | 0.4752 | 0.0655 | 0.065* | |
C5 | 0.5172 (2) | 0.4167 (3) | 0.0776 (2) | 0.0588 (12) | |
H5 | 0.4918 | 0.4906 | 0.0735 | 0.071* | |
C6 | 0.47621 (19) | 0.3203 (3) | 0.08801 (15) | 0.0405 (8) | |
H6 | 0.4215 | 0.3269 | 0.0908 | 0.049* | |
C7 | 0.38051 (16) | 0.0866 (2) | 0.17413 (13) | 0.0274 (6) | |
C8 | 0.39694 (17) | 0.1803 (3) | 0.21165 (13) | 0.0322 (7) | |
H8 | 0.4369 | 0.2347 | 0.2065 | 0.039* | |
C9 | 0.35514 (19) | 0.1980 (3) | 0.25630 (14) | 0.0388 (8) | |
H9 | 0.3670 | 0.2626 | 0.2825 | 0.047* | |
C10 | 0.29689 (18) | 0.1208 (3) | 0.26324 (14) | 0.0401 (8) | |
H10 | 0.2677 | 0.1325 | 0.2936 | 0.048* | |
C11 | 0.28053 (19) | 0.0263 (3) | 0.22647 (15) | 0.0440 (8) | |
H11 | 0.2398 | −0.0270 | 0.2313 | 0.053* | |
C12 | 0.32212 (18) | 0.0084 (3) | 0.18217 (14) | 0.0360 (7) | |
H12 | 0.3108 | −0.0578 | 0.1571 | 0.043* | |
C13 | 0.51757 (16) | −0.0901 (2) | 0.11998 (13) | 0.0273 (6) | |
C14 | 0.55751 (18) | −0.1198 (3) | 0.17666 (14) | 0.0362 (7) | |
H14 | 0.5541 | −0.0703 | 0.2091 | 0.043* | |
C15 | 0.6013 (2) | −0.2208 (3) | 0.18666 (16) | 0.0471 (9) | |
H15 | 0.6289 | −0.2403 | 0.2260 | 0.057* | |
C16 | 0.6057 (2) | −0.2920 (3) | 0.14035 (17) | 0.0481 (9) | |
H16 | 0.6357 | −0.3622 | 0.1470 | 0.058* | |
C17 | 0.56648 (19) | −0.2633 (3) | 0.08336 (16) | 0.0429 (8) | |
H17 | 0.5698 | −0.3128 | 0.0509 | 0.051* | |
C18 | 0.52294 (18) | −0.1627 (3) | 0.07337 (14) | 0.0343 (7) | |
H18 | 0.4959 | −0.1434 | 0.0339 | 0.041* | |
C19 | 0.32228 (16) | −0.0224 (3) | 0.01683 (13) | 0.0284 (6) | |
C20 | 0.26582 (15) | −0.0155 (2) | −0.04141 (12) | 0.0254 (6) | |
C21 | 0.21399 (15) | −0.1064 (3) | −0.05994 (12) | 0.0256 (6) | |
H21 | 0.2129 | −0.1711 | −0.0344 | 0.031* | |
C22 | 0.16189 (16) | −0.1063 (3) | −0.11491 (13) | 0.0273 (6) | |
C23 | 0.16184 (15) | −0.0078 (3) | −0.14992 (12) | 0.0261 (6) | |
C24 | 0.21327 (16) | 0.0828 (2) | −0.13199 (14) | 0.0308 (7) | |
H24 | 0.2130 | 0.1479 | −0.1575 | 0.037* | |
C25 | 0.26543 (17) | 0.0793 (2) | −0.07809 (13) | 0.0313 (7) | |
H25 | 0.3019 | 0.1415 | −0.0655 | 0.038* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.02476 (11) | 0.02769 (12) | 0.02374 (12) | −0.00404 (8) | 0.00363 (8) | 0.00116 (8) |
Cl1 | 0.0303 (4) | 0.0441 (5) | 0.0326 (4) | −0.0028 (4) | −0.0057 (3) | 0.0024 (4) |
O1 | 0.0331 (11) | 0.0351 (12) | 0.0289 (12) | −0.0117 (9) | −0.0041 (9) | 0.0014 (9) |
O2 | 0.0369 (12) | 0.0395 (12) | 0.0297 (12) | −0.0092 (10) | −0.0029 (9) | 0.0074 (10) |
N1 | 0.0502 (16) | 0.0387 (16) | 0.0394 (17) | −0.0227 (14) | −0.0078 (13) | 0.0065 (13) |
C1 | 0.0272 (14) | 0.0265 (15) | 0.0246 (16) | −0.0067 (12) | 0.0045 (12) | −0.0027 (12) |
C2 | 0.0314 (15) | 0.0339 (17) | 0.0288 (17) | −0.0021 (13) | 0.0097 (13) | −0.0041 (13) |
C3 | 0.0351 (17) | 0.041 (2) | 0.054 (2) | −0.0092 (15) | 0.0212 (16) | −0.0066 (16) |
C4 | 0.060 (2) | 0.0320 (19) | 0.081 (3) | −0.0147 (18) | 0.039 (2) | −0.0052 (19) |
C5 | 0.059 (2) | 0.0281 (19) | 0.099 (3) | 0.0026 (17) | 0.039 (2) | 0.0066 (19) |
C6 | 0.0355 (17) | 0.0327 (18) | 0.059 (2) | 0.0003 (14) | 0.0226 (17) | 0.0025 (16) |
C7 | 0.0268 (15) | 0.0314 (16) | 0.0237 (16) | 0.0033 (12) | 0.0047 (12) | 0.0048 (12) |
C8 | 0.0320 (15) | 0.0332 (17) | 0.0311 (17) | 0.0003 (14) | 0.0064 (13) | 0.0069 (14) |
C9 | 0.0464 (19) | 0.0411 (19) | 0.0282 (18) | 0.0074 (16) | 0.0063 (15) | 0.0028 (14) |
C10 | 0.0379 (18) | 0.053 (2) | 0.0324 (19) | 0.0078 (17) | 0.0147 (15) | 0.0082 (16) |
C11 | 0.0345 (18) | 0.058 (2) | 0.043 (2) | −0.0061 (17) | 0.0149 (16) | 0.0109 (18) |
C12 | 0.0338 (16) | 0.0393 (19) | 0.0352 (18) | −0.0028 (15) | 0.0079 (14) | 0.0028 (15) |
C13 | 0.0230 (14) | 0.0264 (15) | 0.0311 (17) | −0.0065 (12) | 0.0030 (12) | 0.0013 (12) |
C14 | 0.0399 (18) | 0.0315 (17) | 0.0327 (18) | 0.0008 (15) | −0.0021 (14) | 0.0000 (14) |
C15 | 0.050 (2) | 0.041 (2) | 0.045 (2) | 0.0030 (17) | 0.0005 (17) | 0.0078 (17) |
C16 | 0.048 (2) | 0.0318 (19) | 0.064 (3) | 0.0057 (16) | 0.0116 (19) | 0.0083 (18) |
C17 | 0.048 (2) | 0.0345 (19) | 0.051 (2) | −0.0030 (16) | 0.0201 (18) | −0.0054 (16) |
C18 | 0.0394 (17) | 0.0342 (18) | 0.0292 (18) | −0.0064 (14) | 0.0075 (14) | −0.0024 (14) |
C19 | 0.0229 (14) | 0.0331 (16) | 0.0284 (16) | −0.0015 (13) | 0.0040 (12) | −0.0002 (14) |
C20 | 0.0199 (13) | 0.0269 (15) | 0.0291 (16) | −0.0005 (12) | 0.0043 (12) | 0.0007 (13) |
C21 | 0.0257 (14) | 0.0272 (15) | 0.0242 (16) | −0.0013 (12) | 0.0056 (12) | 0.0035 (12) |
C22 | 0.0222 (14) | 0.0293 (15) | 0.0315 (17) | −0.0029 (12) | 0.0082 (12) | −0.0034 (13) |
C23 | 0.0203 (13) | 0.0318 (16) | 0.0239 (16) | 0.0023 (12) | 0.0001 (11) | −0.0031 (13) |
C24 | 0.0254 (15) | 0.0274 (16) | 0.0372 (19) | −0.0005 (12) | 0.0012 (13) | 0.0066 (13) |
C25 | 0.0261 (15) | 0.0312 (17) | 0.0336 (18) | −0.0040 (12) | −0.0001 (13) | 0.0005 (13) |
Geometric parameters (Å, º) top
Sn1—O1 | 2.048 (2) | C10—C11 | 1.382 (5) |
Sn1—C7 | 2.122 (3) | C10—H10 | 0.9600 |
Sn1—C13 | 2.121 (3) | C11—C12 | 1.390 (4) |
Sn1—C1 | 2.123 (3) | C11—H11 | 0.9602 |
Cl1—C23 | 1.739 (3) | C12—H12 | 0.9600 |
O1—C19 | 1.314 (3) | C13—C14 | 1.389 (4) |
O2—C19 | 1.228 (3) | C13—C18 | 1.391 (4) |
N1—C22 | 1.371 (4) | C14—C15 | 1.387 (4) |
N1—H1A | 0.8800 | C14—H14 | 0.9600 |
N1—H1B | 0.8800 | C15—C16 | 1.372 (5) |
C1—C6 | 1.395 (4) | C15—H15 | 0.9600 |
C1—C2 | 1.397 (4) | C16—C17 | 1.389 (5) |
C2—C3 | 1.384 (4) | C16—H16 | 0.9600 |
C2—H2 | 0.9600 | C17—C18 | 1.381 (4) |
C3—C4 | 1.375 (5) | C17—H17 | 0.9599 |
C3—H3 | 0.9601 | C18—H18 | 0.9600 |
C4—C5 | 1.382 (5) | C19—C20 | 1.486 (4) |
C4—H4 | 0.9601 | C20—C21 | 1.390 (4) |
C5—C6 | 1.372 (4) | C20—C25 | 1.392 (4) |
C5—H5 | 0.9599 | C21—C22 | 1.391 (4) |
C6—H6 | 0.9600 | C21—H21 | 0.9600 |
C7—C8 | 1.385 (4) | C22—C23 | 1.404 (4) |
C7—C12 | 1.397 (4) | C23—C24 | 1.381 (4) |
C8—C9 | 1.399 (4) | C24—C25 | 1.373 (4) |
C8—H8 | 0.9600 | C24—H24 | 0.9599 |
C9—C10 | 1.381 (4) | C25—H25 | 0.9600 |
C9—H9 | 0.9601 | ||
O1—Sn1—C7 | 108.57 (10) | C11—C12—C7 | 120.1 (3) |
O1—Sn1—C13 | 109.67 (10) | C11—C12—H12 | 120.0 |
C7—Sn1—C13 | 113.91 (11) | C7—C12—H12 | 119.9 |
O1—Sn1—C1 | 95.79 (9) | C14—C13—C18 | 118.8 (3) |
C7—Sn1—C1 | 112.94 (11) | C14—C13—Sn1 | 118.1 (2) |
C13—Sn1—C1 | 114.30 (11) | C18—C13—Sn1 | 123.1 (2) |
C19—O1—Sn1 | 116.10 (18) | C15—C14—C13 | 120.6 (3) |
C22—N1—H1A | 120.0 | C15—C14—H14 | 120.0 |
C22—N1—H1B | 120.0 | C13—C14—H14 | 119.4 |
H1A—N1—H1B | 120.0 | C16—C15—C14 | 120.0 (3) |
C6—C1—C2 | 117.9 (3) | C16—C15—H15 | 120.2 |
C6—C1—Sn1 | 121.3 (2) | C14—C15—H15 | 119.8 |
C2—C1—Sn1 | 120.8 (2) | C15—C16—C17 | 120.2 (3) |
C3—C2—C1 | 120.5 (3) | C15—C16—H16 | 120.4 |
C3—C2—H2 | 120.1 | C17—C16—H16 | 119.4 |
C1—C2—H2 | 119.3 | C18—C17—C16 | 119.8 (3) |
C4—C3—C2 | 120.4 (3) | C18—C17—H17 | 119.9 |
C4—C3—H3 | 119.2 | C16—C17—H17 | 120.2 |
C2—C3—H3 | 120.4 | C17—C18—C13 | 120.6 (3) |
C3—C4—C5 | 119.7 (3) | C17—C18—H18 | 119.4 |
C3—C4—H4 | 119.8 | C13—C18—H18 | 120.0 |
C5—C4—H4 | 120.4 | O2—C19—O1 | 122.7 (3) |
C6—C5—C4 | 120.2 (3) | O2—C19—C20 | 123.0 (3) |
C6—C5—H5 | 120.6 | O1—C19—C20 | 114.3 (2) |
C4—C5—H5 | 119.2 | C21—C20—C25 | 119.7 (3) |
C5—C6—C1 | 121.2 (3) | C21—C20—C19 | 119.3 (3) |
C5—C6—H6 | 119.6 | C25—C20—C19 | 121.0 (3) |
C1—C6—H6 | 119.1 | C22—C21—C20 | 121.7 (3) |
C8—C7—C12 | 118.9 (3) | C22—C21—H21 | 118.1 |
C8—C7—Sn1 | 118.7 (2) | C20—C21—H21 | 120.1 |
C12—C7—Sn1 | 122.4 (2) | N1—C22—C21 | 121.7 (3) |
C7—C8—C9 | 120.9 (3) | N1—C22—C23 | 121.4 (3) |
C7—C8—H8 | 119.6 | C21—C22—C23 | 116.8 (3) |
C9—C8—H8 | 119.4 | C24—C23—C22 | 121.9 (3) |
C10—C9—C8 | 119.6 (3) | C24—C23—Cl1 | 120.1 (2) |
C10—C9—H9 | 119.7 | C22—C23—Cl1 | 118.1 (2) |
C8—C9—H9 | 120.8 | C25—C24—C23 | 120.1 (3) |
C11—C10—C9 | 120.1 (3) | C25—C24—H24 | 119.9 |
C11—C10—H10 | 119.8 | C23—C24—H24 | 119.9 |
C9—C10—H10 | 120.1 | C24—C25—C20 | 119.7 (3) |
C10—C11—C12 | 120.5 (3) | C24—C25—H25 | 120.7 |
C10—C11—H11 | 119.9 | C20—C25—H25 | 119.6 |
C12—C11—H11 | 119.6 | ||
C7—Sn1—O1—C19 | −65.3 (2) | C7—Sn1—C13—C14 | −42.5 (3) |
C13—Sn1—O1—C19 | 59.8 (2) | C1—Sn1—C13—C14 | 89.4 (2) |
C1—Sn1—O1—C19 | 178.1 (2) | O1—Sn1—C13—C18 | 14.1 (3) |
O1—Sn1—C1—C6 | 66.7 (3) | C7—Sn1—C13—C18 | 136.0 (2) |
C7—Sn1—C1—C6 | −46.3 (3) | C1—Sn1—C13—C18 | −92.1 (2) |
C13—Sn1—C1—C6 | −178.7 (2) | C18—C13—C14—C15 | −0.6 (4) |
O1—Sn1—C1—C2 | −111.9 (2) | Sn1—C13—C14—C15 | 177.9 (2) |
C7—Sn1—C1—C2 | 135.1 (2) | C13—C14—C15—C16 | 0.3 (5) |
C13—Sn1—C1—C2 | 2.7 (3) | C14—C15—C16—C17 | 0.0 (5) |
C6—C1—C2—C3 | −0.2 (4) | C15—C16—C17—C18 | 0.0 (5) |
Sn1—C1—C2—C3 | 178.5 (2) | C16—C17—C18—C13 | −0.4 (4) |
C1—C2—C3—C4 | −0.3 (5) | C14—C13—C18—C17 | 0.7 (4) |
C2—C3—C4—C5 | 1.1 (6) | Sn1—C13—C18—C17 | −177.8 (2) |
C3—C4—C5—C6 | −1.4 (7) | Sn1—O1—C19—O2 | −3.4 (4) |
C4—C5—C6—C1 | 0.9 (6) | Sn1—O1—C19—C20 | 176.79 (17) |
C2—C1—C6—C5 | −0.1 (5) | O2—C19—C20—C21 | −5.7 (4) |
Sn1—C1—C6—C5 | −178.8 (3) | O1—C19—C20—C21 | 174.1 (2) |
O1—Sn1—C7—C8 | −121.0 (2) | O2—C19—C20—C25 | 175.8 (3) |
C13—Sn1—C7—C8 | 116.5 (2) | O1—C19—C20—C25 | −4.4 (4) |
C1—Sn1—C7—C8 | −16.1 (3) | C25—C20—C21—C22 | 0.8 (4) |
O1—Sn1—C7—C12 | 61.9 (3) | C19—C20—C21—C22 | −177.7 (2) |
C13—Sn1—C7—C12 | −60.6 (3) | C20—C21—C22—N1 | 174.7 (3) |
C1—Sn1—C7—C12 | 166.8 (2) | C20—C21—C22—C23 | −2.5 (4) |
C12—C7—C8—C9 | −1.0 (4) | N1—C22—C23—C24 | −174.5 (3) |
Sn1—C7—C8—C9 | −178.2 (2) | C21—C22—C23—C24 | 2.7 (4) |
C7—C8—C9—C10 | 0.3 (4) | N1—C22—C23—Cl1 | 4.7 (4) |
C8—C9—C10—C11 | 0.4 (5) | C21—C22—C23—Cl1 | −178.05 (19) |
C9—C10—C11—C12 | −0.3 (5) | C22—C23—C24—C25 | −1.2 (4) |
C10—C11—C12—C7 | −0.6 (5) | Cl1—C23—C24—C25 | 179.5 (2) |
C8—C7—C12—C11 | 1.2 (5) | C23—C24—C25—C20 | −0.5 (4) |
Sn1—C7—C12—C11 | 178.3 (2) | C21—C20—C25—C24 | 0.7 (4) |
O1—Sn1—C13—C14 | −164.4 (2) | C19—C20—C25—C24 | 179.2 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2i | 0.88 | 2.24 | 3.059 (3) | 156 |
N1—H1B···Cl1 | 0.88 | 2.55 | 2.962 (3) | 109 |
Symmetry code: (i) −x+1/2, −y−1/2, −z. |