Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100002432/qb0186sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100002432/qb0186Isup2.hkl |
CCDC reference: 143325
The crystal used for the X-ray measurements was a crystal that was selected from a batch of triphenyltin N,N-3-oxapentamethylenethiocarbamoylthioacetate hydrate (Ng & Hook, 1999) crystals that had been kept in a bottle for several years. Whether the crystal had resulted from the solid-state decomposition of the hydrate or whether 3-ureidopropionic acid was a contaminant in the N,N-3-oxapentamethylenethiocarbamoylacetic acid that reacted with triphenyltin hydroxide to form the 3-ureidopropionate could not be ascertained.
The structure was refined using 6262 reflections (3510 unique and an additional 2752 Friedel pairs); the chirality of the crystal used in the measurements was established by the Flack parameter, which refined to -0.04 (2).
Data collection: CAD-4-PC (Kretschmar, 1994); cell refinement: CELDIM in CAD-4 VAX/PC Fortran System (Enraf-Nonius, 1988); data reduction: XCAD4 (Harms, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.
[Sn(C6H5)3(C4H7N2O3)] | Dx = 1.483 Mg m−3 |
Mr = 481.11 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 25 reflections |
a = 11.2608 (6) Å | θ = 14.5–15.0° |
b = 13.0527 (5) Å | µ = 1.21 mm−1 |
c = 14.6607 (6) Å | T = 298 K |
V = 2154.9 (2) Å3 | Cube, colorless |
Z = 4 | 0.43 × 0.43 × 0.43 mm |
F(000) = 968 |
Enraf-Nonius CAD-4 diffractometer | 5401 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.015 |
Graphite monochromator | θmax = 30.0°, θmin = 2.1° |
ω scans | h = −15→15 |
Absorption correction: semi-empirical (using intensity measurements) ψ scans [North et al. (1968) in WinGX (Farrugia, 1999)] | k = 0→18 |
Tmin = 0.666, Tmax = 0.724 | l = 0→20 |
7014 measured reflections | 3 standard reflections every 60 min |
6262 independent reflections | intensity decay: 3% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.077 | w = 1/[σ2(Fo2) + (0.0412P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
6262 reflections | Δρmax = 0.83 e Å−3 |
253 parameters | Δρmin = −0.31 e Å−3 |
0 restraints | Absolute structure: Flack & Schwarzenbach, 1988 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.04 (2) |
[Sn(C6H5)3(C4H7N2O3)] | V = 2154.9 (2) Å3 |
Mr = 481.11 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 11.2608 (6) Å | µ = 1.21 mm−1 |
b = 13.0527 (5) Å | T = 298 K |
c = 14.6607 (6) Å | 0.43 × 0.43 × 0.43 mm |
Enraf-Nonius CAD-4 diffractometer | 5401 reflections with I > 2σ(I) |
Absorption correction: semi-empirical (using intensity measurements) ψ scans [North et al. (1968) in WinGX (Farrugia, 1999)] | Rint = 0.015 |
Tmin = 0.666, Tmax = 0.724 | 3 standard reflections every 60 min |
7014 measured reflections | intensity decay: 3% |
6262 independent reflections |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.077 | Δρmax = 0.83 e Å−3 |
S = 1.06 | Δρmin = −0.31 e Å−3 |
6262 reflections | Absolute structure: Flack & Schwarzenbach, 1988 |
253 parameters | Absolute structure parameter: −0.04 (2) |
0 restraints |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.83471 (2) | 0.02473 (2) | 0.78624 (1) | 0.04325 (6) | |
O1 | 0.6931 (2) | 0.0605 (2) | 0.8805 (1) | 0.050 (1) | |
O2 | 0.7772 (2) | 0.2111 (2) | 0.9042 (2) | 0.065 (1) | |
O3 | 0.5145 (2) | 0.0133 (2) | 1.1832 (2) | 0.057 (1) | |
N1 | 0.4347 (2) | 0.1189 (2) | 1.0794 (2) | 0.054 (1) | |
N2 | 0.3713 (3) | 0.1241 (3) | 1.2266 (2) | 0.074 (1) | |
C1 | 0.7873 (3) | 0.1392 (3) | 0.6884 (2) | 0.049 (1) | |
C2 | 0.8612 (3) | 0.1734 (3) | 0.6199 (2) | 0.062 (1) | |
C3 | 0.8256 (5) | 0.2489 (4) | 0.5590 (3) | 0.081 (1) | |
C4 | 0.7146 (5) | 0.2901 (4) | 0.5655 (3) | 0.082 (1) | |
C5 | 0.6381 (4) | 0.2579 (4) | 0.6325 (3) | 0.074 (1) | |
C6 | 0.6742 (4) | 0.1830 (3) | 0.6934 (2) | 0.060 (1) | |
C7 | 0.9659 (3) | 0.0260 (3) | 0.8909 (2) | 0.046 (1) | |
C8 | 0.9413 (3) | −0.0186 (3) | 0.9748 (2) | 0.056 (1) | |
C9 | 1.0256 (3) | −0.0186 (4) | 1.0436 (2) | 0.067 (1) | |
C10 | 1.1341 (3) | 0.0263 (4) | 1.0308 (2) | 0.064 (1) | |
C11 | 1.1594 (4) | 0.0707 (3) | 0.9479 (3) | 0.065 (1) | |
C12 | 1.0772 (3) | 0.0703 (3) | 0.8793 (2) | 0.056 (1) | |
C13 | 0.7587 (3) | −0.1232 (3) | 0.7646 (2) | 0.049 (1) | |
C14 | 0.7995 (4) | −0.2081 (3) | 0.8092 (3) | 0.070 (1) | |
C15 | 0.7465 (5) | −0.3034 (4) | 0.7971 (4) | 0.086 (1) | |
C16 | 0.6528 (5) | −0.3131 (4) | 0.7384 (4) | 0.090 (2) | |
C17 | 0.6142 (5) | −0.2331 (5) | 0.6942 (4) | 0.101 (2) | |
C18 | 0.6655 (4) | −0.1361 (4) | 0.7058 (3) | 0.079 (1) | |
C19 | 0.7031 (3) | 0.1458 (3) | 0.9226 (2) | 0.048 (1) | |
C20 | 0.6163 (3) | 0.1648 (3) | 0.9995 (2) | 0.060 (1) | |
C21 | 0.5160 (3) | 0.0895 (3) | 1.0070 (2) | 0.051 (1) | |
C22 | 0.4450 (3) | 0.0845 (3) | 1.1644 (2) | 0.046 (1) | |
H1 | 0.3775 | 0.1602 | 1.0668 | 0.082* | |
H2a | 0.3710 | 0.1004 | 1.2813 | 0.111* | |
H2b | 0.3242 | 0.1732 | 1.2119 | 0.111* | |
H2 | 0.9367 | 0.1452 | 0.6144 | 0.093* | |
H3 | 0.8774 | 0.2714 | 0.5138 | 0.121* | |
H4 | 0.6906 | 0.3402 | 0.5244 | 0.123* | |
H5 | 0.5625 | 0.2861 | 0.6369 | 0.111* | |
H6 | 0.6221 | 0.1614 | 0.7386 | 0.090* | |
H8 | 0.8676 | −0.0487 | 0.9849 | 0.084* | |
H9 | 1.0082 | −0.0494 | 1.0992 | 0.100* | |
H10 | 1.1901 | 0.0268 | 1.0774 | 0.096* | |
H11 | 1.2330 | 0.1012 | 0.9384 | 0.097* | |
H12 | 1.0961 | 0.1004 | 0.8236 | 0.084* | |
H14 | 0.8640 | −0.2021 | 0.8484 | 0.105* | |
H15 | 0.7746 | −0.3601 | 0.8288 | 0.129* | |
H16 | 0.6168 | −0.3765 | 0.7301 | 0.136* | |
H17 | 0.5509 | −0.2406 | 0.6539 | 0.151* | |
H18 | 0.6362 | −0.0803 | 0.6734 | 0.119* | |
H20a | 0.6599 | 0.1645 | 1.0566 | 0.090* | |
H20b | 0.5829 | 0.2328 | 0.9919 | 0.090* | |
H21a | 0.4734 | 0.0867 | 0.9495 | 0.076* | |
H21b | 0.5476 | 0.0219 | 1.0195 | 0.076* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0412 (1) | 0.0507 (1) | 0.0379 (1) | −0.0014 (1) | 0.0020 (1) | −0.0020 (1) |
O1 | 0.047 (1) | 0.056 (1) | 0.047 (1) | −0.008 (1) | 0.010 (1) | −0.007 (1) |
O2 | 0.065 (2) | 0.067 (2) | 0.062 (2) | −0.019 (1) | 0.012 (1) | −0.006 (1) |
O3 | 0.056 (1) | 0.068 (2) | 0.046 (1) | 0.018 (1) | −0.008 (1) | 0.001 (1) |
N1 | 0.047 (1) | 0.072 (2) | 0.044 (1) | 0.020 (1) | 0.009 (1) | 0.012 (1) |
N2 | 0.093 (2) | 0.086 (2) | 0.043 (2) | 0.034 (2) | 0.015 (2) | 0.000 (2) |
C1 | 0.052 (2) | 0.054 (2) | 0.041 (2) | −0.004 (2) | 0.000 (1) | −0.001 (1) |
C2 | 0.067 (2) | 0.063 (2) | 0.057 (2) | 0.004 (1) | 0.012 (2) | 0.005 (2) |
C3 | 0.106 (3) | 0.078 (3) | 0.058 (2) | 0.002 (3) | 0.014 (3) | 0.019 (2) |
C4 | 0.113 (4) | 0.071 (3) | 0.063 (2) | 0.010 (3) | −0.020 (3) | 0.012 (2) |
C5 | 0.069 (3) | 0.076 (3) | 0.077 (3) | 0.014 (2) | −0.018 (2) | 0.007 (2) |
C6 | 0.052 (2) | 0.068 (2) | 0.060 (2) | 0.004 (2) | −0.007 (2) | 0.004 (2) |
C7 | 0.044 (2) | 0.052 (2) | 0.040 (1) | 0.002 (2) | 0.001 (1) | −0.006 (2) |
C8 | 0.051 (2) | 0.072 (2) | 0.045 (2) | −0.006 (2) | 0.003 (1) | 0.005 (2) |
C9 | 0.074 (2) | 0.082 (2) | 0.044 (2) | 0.005 (2) | −0.003 (2) | 0.003 (2) |
C10 | 0.063 (2) | 0.072 (2) | 0.058 (2) | 0.002 (2) | −0.017 (2) | −0.007 (2) |
C11 | 0.049 (2) | 0.072 (2) | 0.074 (2) | −0.011 (2) | −0.006 (2) | −0.003 (2) |
C12 | 0.048 (2) | 0.071 (2) | 0.049 (2) | −0.010 (2) | 0.003 (1) | 0.003 (2) |
C13 | 0.050 (2) | 0.055 (2) | 0.042 (2) | −0.003 (2) | 0.005 (1) | −0.005 (1) |
C14 | 0.087 (3) | 0.061 (2) | 0.061 (2) | −0.006 (2) | −0.001 (2) | −0.004 (2) |
C15 | 0.118 (4) | 0.058 (2) | 0.082 (3) | −0.011 (3) | 0.023 (3) | −0.004 (2) |
C16 | 0.097 (4) | 0.082 (3) | 0.092 (3) | −0.039 (3) | 0.034 (3) | −0.031 (3) |
C17 | 0.082 (3) | 0.114 (5) | 0.106 (4) | −0.033 (3) | −0.011 (3) | −0.028 (3) |
C18 | 0.073 (2) | 0.084 (3) | 0.081 (3) | −0.012 (2) | −0.022 (3) | −0.004 (2) |
C19 | 0.044 (2) | 0.057 (2) | 0.042 (2) | −0.004 (1) | 0.003 (1) | −0.002 (1) |
C20 | 0.057 (2) | 0.071 (2) | 0.052 (2) | −0.011 (2) | 0.010 (2) | −0.012 (2) |
C21 | 0.047 (2) | 0.064 (2) | 0.041 (2) | 0.002 (2) | 0.007 (1) | 0.001 (2) |
C22 | 0.038 (1) | 0.057 (2) | 0.043 (2) | 0.000 (1) | −0.001 (1) | −0.002 (1) |
Sn1—C1 | 2.138 (3) | C16—C17 | 1.304 (8) |
Sn1—C7 | 2.130 (3) | C17—C18 | 1.403 (7) |
Sn1—C13 | 2.136 (3) | C19—C20 | 1.513 (4) |
Sn1—O1 | 2.161 (2) | C20—C21 | 1.501 (5) |
Sn1—O3i | 2.327 (2) | N1—H1 | 0.8600 |
O1—C19 | 1.278 (4) | N2—H2a | 0.8600 |
O2—C19 | 1.223 (4) | N2—H2b | 0.8600 |
O3—C22 | 1.245 (4) | C2—H2 | 0.9300 |
N1—C22 | 1.329 (4) | C3—H3 | 0.9300 |
N1—C21 | 1.454 (4) | C4—H4 | 0.9300 |
N2—C22 | 1.337 (4) | C5—H5 | 0.9300 |
C1—C2 | 1.378 (5) | C6—H6 | 0.9300 |
C1—C6 | 1.398 (5) | C8—H8 | 0.9300 |
C2—C3 | 1.390 (6) | C9—H9 | 0.9300 |
C3—C4 | 1.364 (7) | C10—H10 | 0.9300 |
C4—C5 | 1.372 (6) | C11—H11 | 0.9300 |
C5—C6 | 1.384 (6) | C12—H12 | 0.9300 |
C7—C8 | 1.389 (4) | C14—H14 | 0.9300 |
C7—C12 | 1.390 (4) | C15—H15 | 0.9300 |
C8—C9 | 1.384 (5) | C16—H16 | 0.9300 |
C9—C10 | 1.368 (6) | C17—H17 | 0.9300 |
C10—C11 | 1.376 (5) | C18—H18 | 0.9300 |
C11—C12 | 1.367 (5) | C20—H20a | 0.9700 |
C13—C14 | 1.368 (5) | C20—H20b | 0.9700 |
C13—C18 | 1.368 (5) | C21—H21a | 0.9700 |
C14—C15 | 1.390 (6) | C21—H21b | 0.9700 |
C15—C16 | 1.367 (8) | ||
C1—Sn1—C7 | 130.6 (1) | C22—N1—H1 | 118.6 |
C1—Sn1—C13 | 115.6 (1) | C21—N1—H1 | 118.6 |
C1—Sn1—O1 | 95.4 (1) | C22—N2—H2a | 120.0 |
C1—Sn1—O3i | 84.0 (1) | C22—N2—H2b | 120.0 |
C7—Sn1—C13 | 113.1 (1) | H2a—N2—H2b | 120.0 |
C7—Sn1—O1 | 92.9 (1) | C1—C2—H2 | 119.2 |
C7—Sn1—O3i | 87.9 (1) | C3—C2—H2 | 119.2 |
C13—Sn1—O1 | 89.7 (1) | C4—C3—H3 | 120.0 |
C13—Sn1—O3i | 90.2 (1) | C2—C3—H3 | 120.0 |
O1—Sn1—O3i | 179.2 (1) | C3—C4—H4 | 119.8 |
C19—O1—Sn1 | 115.6 (2) | C5—C4—H4 | 119.8 |
C22—O3—Sn1ii | 139.6 (2) | C4—C5—H5 | 120.2 |
C22—N1—C21 | 122.7 (3) | C6—C5—H5 | 120.2 |
C2—C1—C6 | 117.1 (3) | C5—C6—H6 | 119.2 |
C2—C1—Sn1 | 124.3 (3) | C1—C6—H6 | 119.2 |
C6—C1—Sn1 | 118.6 (2) | C9—C8—H8 | 119.7 |
C1—C2—C3 | 121.6 (4) | C7—C8—H8 | 119.7 |
C4—C3—C2 | 119.9 (4) | C10—C9—H9 | 119.6 |
C3—C4—C5 | 120.3 (4) | C8—C9—H9 | 119.6 |
C4—C5—C6 | 119.5 (4) | C9—C10—H10 | 120.5 |
C5—C6—C1 | 121.5 (4) | C11—C10—H10 | 120.5 |
C8—C7—C12 | 117.5 (3) | C12—C11—H11 | 119.7 |
C8—C7—Sn1 | 119.8 (2) | C10—C11—H11 | 119.7 |
C12—C7—Sn1 | 122.7 (2) | C11—C12—H12 | 119.3 |
C9—C8—C7 | 120.6 (3) | C7—C12—H12 | 119.3 |
C10—C9—C8 | 120.8 (4) | C13—C14—H14 | 119.3 |
C9—C10—C11 | 119.1 (3) | C15—C14—H14 | 119.3 |
C12—C11—C10 | 120.6 (4) | C16—C15—H15 | 120.2 |
C11—C12—C7 | 121.5 (3) | C14—C15—H15 | 120.2 |
C14—C13—C18 | 117.3 (4) | C17—C16—H16 | 120.1 |
C14—C13—Sn1 | 121.8 (3) | C15—C16—H16 | 120.1 |
C18—C13—Sn1 | 120.9 (3) | C16—C17—H17 | 119.2 |
C13—C14—C15 | 121.3 (4) | C18—C17—H17 | 119.2 |
C16—C15—C14 | 119.7 (5) | C13—C18—H18 | 119.9 |
C17—C16—C15 | 119.8 (5) | C17—C18—H18 | 119.9 |
C16—C17—C18 | 121.6 (5) | C21—C20—H20a | 108.4 |
C13—C18—C17 | 120.3 (5) | C19—C20—H20a | 108.4 |
O2—C19—O1 | 124.2 (3) | C21—C20—H20b | 108.4 |
O2—C19—C20 | 119.3 (3) | C19—C20—H20b | 108.4 |
O1—C19—C20 | 116.5 (3) | H20a—C20—H20b | 107.4 |
C21—C20—C19 | 115.6 (3) | N1—C21—H21a | 109.5 |
N1—C21—C20 | 110.8 (3) | C20—C21—H21a | 109.5 |
O3—C22—N1 | 120.9 (3) | N1—C21—H21b | 109.5 |
O3—C22—N2 | 121.8 (3) | C20—C21—H21b | 109.5 |
N1—C22—N2 | 117.0 (3) | H21a—C21—H21b | 108.1 |
Symmetry codes: (i) −x+3/2, −y, z−1/2; (ii) −x+3/2, −y, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2iii | 0.86 | 2.07 | 2.851 (4) | 151 |
N2—H2b···O2iii | 0.86 | 2.34 | 3.070 (4) | 144 |
Symmetry code: (iii) x−1/2, −y+1/2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | [Sn(C6H5)3(C4H7N2O3)] |
Mr | 481.11 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 298 |
a, b, c (Å) | 11.2608 (6), 13.0527 (5), 14.6607 (6) |
V (Å3) | 2154.9 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.21 |
Crystal size (mm) | 0.43 × 0.43 × 0.43 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | Semi-empirical (using intensity measurements) ψ scans [North et al. (1968) in WinGX (Farrugia, 1999)] |
Tmin, Tmax | 0.666, 0.724 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7014, 6262, 5401 |
Rint | 0.015 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.077, 1.06 |
No. of reflections | 6262 |
No. of parameters | 253 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.83, −0.31 |
Absolute structure | Flack & Schwarzenbach, 1988 |
Absolute structure parameter | −0.04 (2) |
Computer programs: CAD-4-PC (Kretschmar, 1994), CELDIM in CAD-4 VAX/PC Fortran System (Enraf-Nonius, 1988), XCAD4 (Harms, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97.
Triphenyltin alkanoates generally adopt carboxylate-bridged chain structures whose chains have either a flat or a helical conformation (Ng et al., 1988; Tiekink, 1991, 1994). A strongly Lewis-basic site in the alkanoate group can compete successfully with the carboxyl O atom, and this is exemplified by the diethylphosphonoacetate (Ng & Kumar Das, 1994) and 3-diethylphosphonopropionate (Ng & Kumar Das, 1996). The ureido O atom in the 3-ureidopropionate is probably more basic than the phosphoryl O atoms in 3-diethylphosphonopionate [Sn—O 2.116 (2), Sn← O 2.397 (3) Å] as the dative bond [Sn—O = 2.161 (2) Å and Sn← O 2.327 (2) Å] is much shorter than than in the 3-diethylphosphopripionate. Bond dimensions involving the Sn atom in the orthorhombic modification, (I), do not differ much from those found in the monoclinic modification (Lo et al., 1991); the most significant difference is the almost linear O—Sn← O skeleton [O—Sn← O 179.2 (1)°], which contrasts with the bent skeleton [O—Sn← O 171.5 (1)°] of the monoclinic modification. The monoclinic (P21/n) modification which propagates in a zigzag manner along the c axis, adopts a similar hydrogen-bonded [N···O 2.882 (4) Å] architecture.