Orthorhombic modification of tri­phenyl­tin 3-ureidopropionate

The Sn atom in catena-poly­[tri­phenyl­tin(IV)-[mu]-(3-ureidopropionato-O¹:O³)], [Sn(C₆H₅)₃(C₄H₇N₂O₃)]_n, is five-coordinate and has a trans-C₃SnO₂ trigonal-bipyrmidal geometry arising from bridging through the O atom of the ureido fragment of an adjacent carboxyl­ate group. Infinite chains propagate helically along the c axis and adjacent chains are linked by N-H...O [N...O 2.851 (4) Å] hydrogen bonds into layers.

S1. Comment

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.

S2. Experimental

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.

S3. Refinement

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).

Computing details

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.

Catena-poly[triphenyltin-µu-(3-ureidopropionato-O:O')]

Crystal data

[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) Å^3	Cube, colorless
Z = 4	0.43 × 0.43 × 0.43 mm
F(000) = 968

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.077	w = 1/[σ^2(Fo^2) + (0.0412P)^2] where P = (Fo^2 + 2Fc^2)/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)

Special details

Refinement. H atoms: 'Riding, U(H) = 1.5U_eq(C,N).'

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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—O3^i	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—O3^i	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—O3^i	87.9 (1)	C3—C2—H2	119.2
C13—Sn1—O1	89.7 (1)	C4—C3—H3	120.0
C13—Sn1—O3^i	90.2 (1)	C2—C3—H3	120.0
O1—Sn1—O3^i	179.2 (1)	C3—C4—H4	119.8
C19—O1—Sn1	115.6 (2)	C5—C4—H4	119.8
C22—O3—Sn1^ii	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.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^iii	0.86	2.07	2.851 (4)	151
N2—H2b···O2^iii	0.86	2.34	3.070 (4)	144

Symmetry code: (iii) x−1/2, −y+1/2, −z+2.