(2-Carbamoylethyl-κC,O)triiodidotin(IV).

Two independent but virtually identical mol-ecules comprise the asymmetric unit of the title compound, [Sn(C(3)H(6)NO)I(3)]. The CI(3)O coordination geometry around the Sn(IV) atom is defined by a chelating carbamoylethyl ligand (C(1),O-bidentate) and three I atoms, and is based on a distorted trigonal bipyramid with the carbonyl O atom occupying a position trans to one of the I atoms which forms the longer of the Sn-I bonds. The independent mol-ecules are linked via N-H⋯O hydrogen bonds, which leads to the formation on an eight-membered amide {⋯HNCO}(2) synthon. N-H⋯I hydrogen-bonding inter-actions are also present between neighbouring mol-ecules.

Related literature

For background to and for related Sn[OCH(NH2)CH2CH2]Cl3 L structures (L = amide), see: Howie et al. (2011a ▶,b ▶); Wardell et al. (2010 ▶); Tiekink et al. (2006 ▶). For additional geometric analysis, see: Addison et al. (1984 ▶); Spek (2009 ▶).

Experimental

Crystal data

[Sn(C3H6NO)I3]

M = 571.48

Triclinic,

a = 7.8530 (1) Å

b = 10.6264 (1) Å

c = 14.1250 (2) Å

α = 98.801 (1)°

β = 105.523 (1)°

γ = 102.383 (1)°

V = 1081.22 (2) Å3

Z = 4

Mo Kα radiation

μ = 10.87 mm−1

T = 120 K

0.20 × 0.20 × 0.02 mm

Data collection

Bruker–Nonius APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.379, T max = 1.000

14061 measured reflections

4414 independent reflections

4342 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.079

S = 1.12

4414 reflections

163 parameters

H-atom parameters constrained

Δρmax = 1.37 e Å−3

Δρmin = −1.46 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811041778/wm2541sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041778/wm2541Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Sn(C3H6NO)I3]	Z = 4
Mr = 571.48	F(000) = 992
Triclinic, P1	Dx = 3.511 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8530 (1) Å	Cell parameters from 4411 reflections
b = 10.6264 (1) Å	θ = 2.9–27.5°
c = 14.1250 (2) Å	µ = 10.87 mm−1
α = 98.801 (1)°	T = 120 K
β = 105.523 (1)°	Plate, yellow
γ = 102.383 (1)°	0.20 × 0.20 × 0.02 mm
V = 1081.22 (2) Å3

Bruker–Nonius APEXII CCD diffractometer	4414 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	4342 reflections with I > 2σ(I)
10cm confocal mirrors	Rint = 0.039
Detector resolution: 9.091 pixels mm-1	θmax = 26.5°, θmin = 3.0°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −13→13
Tmin = 0.379, Tmax = 1.000	l = −17→17
14061 measured reflections

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0384P)2 + 3.8857P] where P = (Fo2 + 2Fc2)/3
4414 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 1.37 e Å−3
0 restraints	Δρmin = −1.46 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Sn1	0.84744 (4)	0.81052 (3)	0.07941 (2)	0.01343 (9)
I1	0.79233 (5)	0.56511 (3)	0.11465 (2)	0.02019 (10)
I2	1.13298 (5)	0.80096 (3)	−0.00043 (3)	0.02164 (10)
I3	0.58439 (4)	0.79311 (3)	−0.09302 (2)	0.01808 (9)
O1	0.6302 (5)	0.8274 (4)	0.1636 (3)	0.0196 (7)
N1	0.5852 (8)	0.9523 (5)	0.2928 (4)	0.0324 (12)
H1N	0.4849	0.8870	0.2762	0.039*
H2N	0.6529	0.9568	0.3546	0.039*
C1	0.9830 (7)	0.9848 (5)	0.1974 (4)	0.0190 (10)
H1A	1.0707	0.9634	0.2533	0.023*
H1B	1.0533	1.0528	0.1714	0.023*
C2	0.8454 (9)	1.0397 (5)	0.2370 (4)	0.0266 (12)
H2A	0.9052	1.0874	0.3083	0.032*
H2B	0.8057	1.1037	0.1978	0.032*
C3	0.6791 (7)	0.9313 (5)	0.2296 (4)	0.0198 (10)
Sn2	0.27996 (4)	0.67003 (3)	0.46025 (2)	0.01266 (9)
I4	0.61233 (4)	0.84602 (3)	0.54333 (3)	0.01904 (10)
I5	0.02318 (4)	0.80393 (3)	0.43118 (2)	0.01823 (9)
I6	0.25104 (5)	0.60910 (3)	0.64270 (2)	0.02072 (10)
O2	0.3235 (5)	0.6994 (4)	0.3074 (3)	0.0208 (8)
N2	0.3498 (7)	0.5858 (5)	0.1668 (4)	0.0286 (11)
H3N	0.3856	0.6666	0.1585	0.034*
H4N	0.4401	0.5480	0.1716	0.034*
C4	0.2650 (7)	0.4737 (5)	0.3869 (4)	0.0171 (9)
H4A	0.3835	0.4533	0.4140	0.021*
H4B	0.1684	0.4090	0.4005	0.021*
C5	0.2215 (7)	0.4620 (5)	0.2734 (4)	0.0213 (11)
H5A	0.2708	0.3921	0.2449	0.026*
H5B	0.0868	0.4358	0.2414	0.026*
C6	0.3029 (7)	0.5905 (5)	0.2496 (4)	0.0188 (10)

	U11	U22	U33	U12	U13	U23
Sn1	0.01254 (17)	0.01471 (17)	0.01161 (16)	0.00316 (13)	0.00254 (13)	0.00162 (12)
I1	0.02194 (19)	0.01739 (17)	0.02113 (18)	0.00547 (14)	0.00490 (14)	0.00694 (13)
I2	0.01880 (18)	0.02449 (18)	0.02683 (19)	0.00877 (14)	0.01201 (14)	0.00795 (14)
I3	0.01449 (17)	0.02295 (18)	0.01437 (17)	0.00462 (13)	0.00081 (13)	0.00423 (13)
O1	0.0162 (18)	0.0241 (18)	0.0176 (17)	0.0048 (14)	0.0059 (14)	0.0023 (14)
N1	0.044 (3)	0.027 (2)	0.032 (3)	0.009 (2)	0.025 (2)	−0.001 (2)
C1	0.021 (3)	0.013 (2)	0.016 (2)	−0.0025 (19)	0.001 (2)	−0.0023 (18)
C2	0.045 (4)	0.016 (2)	0.024 (3)	0.010 (2)	0.018 (3)	0.003 (2)
C3	0.025 (3)	0.026 (3)	0.016 (2)	0.014 (2)	0.011 (2)	0.008 (2)
Sn2	0.01234 (17)	0.01365 (16)	0.01193 (16)	0.00425 (12)	0.00339 (13)	0.00231 (12)
I4	0.01251 (17)	0.01815 (17)	0.02403 (18)	0.00266 (13)	0.00420 (13)	0.00230 (13)
I5	0.01529 (18)	0.02042 (17)	0.02122 (18)	0.00887 (13)	0.00530 (13)	0.00606 (13)
I6	0.01956 (18)	0.02811 (19)	0.01277 (16)	0.00340 (14)	0.00347 (13)	0.00657 (13)
O2	0.028 (2)	0.0208 (18)	0.0155 (17)	0.0060 (15)	0.0108 (15)	0.0032 (14)
N2	0.035 (3)	0.030 (3)	0.022 (2)	0.005 (2)	0.015 (2)	0.003 (2)
C4	0.022 (3)	0.013 (2)	0.013 (2)	0.0072 (19)	0.0009 (19)	0.0001 (17)
C5	0.022 (3)	0.021 (2)	0.016 (2)	0.002 (2)	0.004 (2)	−0.0031 (19)
C6	0.014 (2)	0.029 (3)	0.016 (2)	0.009 (2)	0.0047 (19)	0.006 (2)

Sn1—C1	2.146 (5)	Sn2—C4	2.147 (5)
Sn1—O1	2.347 (3)	Sn2—O2	2.330 (3)
Sn1—I1	2.6953 (4)	Sn2—I4	2.6987 (4)
Sn1—I2	2.7796 (4)	Sn2—I5	2.6880 (4)
Sn1—I3	2.6904 (4)	Sn2—I6	2.8060 (4)
O1—C3	1.244 (6)	O2—C6	1.262 (6)
N1—C3	1.324 (7)	N2—C6	1.313 (6)
N1—H1N	0.8800	N2—H3N	0.8800
N1—H2N	0.8800	N2—H4N	0.8800
C1—C2	1.521 (7)	C4—C5	1.526 (7)
C1—H1A	0.9900	C4—H4A	0.9900
C1—H1B	0.9900	C4—H4B	0.9900
C2—C3	1.512 (8)	C5—C6	1.506 (7)
C2—H2A	0.9900	C5—H5A	0.9900
C2—H2B	0.9900	C5—H5B	0.9900
C1—Sn1—O1	76.52 (16)	C4—Sn2—O2	77.38 (16)
C1—Sn1—I3	125.92 (14)	C4—Sn2—I5	129.25 (14)
O1—Sn1—I3	87.71 (9)	O2—Sn2—I5	89.69 (9)
C1—Sn1—I1	122.64 (14)	C4—Sn2—I4	118.64 (14)
O1—Sn1—I1	83.18 (9)	O2—Sn2—I4	84.58 (9)
I3—Sn1—I1	105.788 (15)	I5—Sn2—I4	108.400 (14)
C1—Sn1—I2	98.50 (14)	C4—Sn2—I6	96.42 (13)
O1—Sn1—I2	173.92 (9)	O2—Sn2—I6	172.63 (9)
I3—Sn1—I2	98.106 (14)	I5—Sn2—I6	97.373 (13)
I1—Sn1—I2	96.853 (14)	I4—Sn2—I6	95.120 (13)
C3—O1—Sn1	112.5 (3)	C6—O2—Sn2	111.5 (3)
C3—N1—H1N	109.5	C6—N2—H3N	109.5
C3—N1—H2N	109.5	C6—N2—H4N	109.5
H1N—N1—H2N	109.5	H3N—N2—H4N	109.5
C2—C1—Sn1	111.0 (4)	C5—C4—Sn2	110.1 (3)
C2—C1—H1A	109.4	C5—C4—H4A	109.6
Sn1—C1—H1A	109.4	Sn2—C4—H4A	109.6
C2—C1—H1B	109.4	C5—C4—H4B	109.6
Sn1—C1—H1B	109.4	Sn2—C4—H4B	109.6
H1A—C1—H1B	108.0	H4A—C4—H4B	108.1
C3—C2—C1	111.7 (4)	C6—C5—C4	111.5 (4)
C3—C2—H2A	109.3	C6—C5—H5A	109.3
C1—C2—H2A	109.3	C4—C5—H5A	109.3
C3—C2—H2B	109.3	C6—C5—H5B	109.3
C1—C2—H2B	109.3	C4—C5—H5B	109.3
H2A—C2—H2B	107.9	H5A—C5—H5B	108.0
O1—C3—N1	121.5 (5)	O2—C6—N2	121.2 (5)
O1—C3—C2	120.3 (4)	O2—C6—C5	120.6 (4)
N1—C3—C2	118.2 (5)	N2—C6—C5	118.2 (5)
C1—Sn1—O1—C3	6.4 (4)	C4—Sn2—O2—C6	5.8 (3)
I3—Sn1—O1—C3	−121.4 (3)	I5—Sn2—O2—C6	−124.7 (3)
I1—Sn1—O1—C3	132.4 (3)	I4—Sn2—O2—C6	126.8 (3)
O1—Sn1—C1—C2	−19.9 (3)	O2—Sn2—C4—C5	−20.4 (3)
I3—Sn1—C1—C2	57.1 (4)	I5—Sn2—C4—C5	58.6 (4)
I1—Sn1—C1—C2	−92.5 (4)	I4—Sn2—C4—C5	−97.0 (3)
I2—Sn1—C1—C2	163.6 (3)	I6—Sn2—C4—C5	163.6 (3)
Sn1—C1—C2—C3	31.0 (6)	Sn2—C4—C5—C6	32.4 (5)
Sn1—O1—C3—N1	−172.4 (4)	Sn2—O2—C6—N2	−169.0 (4)
Sn1—O1—C3—C2	9.8 (6)	Sn2—O2—C6—C5	11.7 (6)
C1—C2—C3—O1	−27.7 (7)	C4—C5—C6—O2	−30.2 (7)
C1—C2—C3—N1	154.4 (5)	C4—C5—C6—N2	150.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O2	0.88	2.29	3.085 (7)	150
N2—H3n···O1	0.88	2.26	3.018 (7)	145
N2—H4n···I1	0.88	3.06	3.784 (6)	141

Table 1

Selected bond lengths (Å)

Sn1—C1	2.146 (5)
Sn1—O1	2.347 (3)
Sn1—I1	2.6953 (4)
Sn1—I2	2.7796 (4)
Sn1—I3	2.6904 (4)
Sn2—C4	2.147 (5)
Sn2—O2	2.330 (3)
Sn2—I4	2.6987 (4)
Sn2—I5	2.6880 (4)
Sn2—I6	2.8060 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O2	0.88	2.29	3.085 (7)	150
N2—H3n⋯O1	0.88	2.26	3.018 (7)	145
N2—H4n⋯I1	0.88	3.06	3.784 (6)	141