Dicyclo­hexyl­ammonium bis­(chloro­difluoro­acetato-κO)cyclo­pentyl­diphenyl­stannate(IV)

Teo, Y.Y.; Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536808010775

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page m700

doi:10.1107/S1600536808010775

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Dicyclohexylammonium bis(chlorodifluoroacetato-κO)cyclopentyldiphenylstannate(IV)

Yin Yin Teo,^a Kong Mun Lo ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 1 April 2008; accepted 18 April 2008; online 23 April 2008)

The five-coordinate Sn atom in the title mixed organyl stannate compound, (C₁₂H₂₄N)[Sn(C₅H₉)(C₆H₅)₂(C₂ClF₂O₂)], is in a trans-C₃SnO₂ trigonal–bipyramidal coordination environment. The NH₂ groups of the cations act as hydrogen-bond donors to two symmetry-related anions, resulting in the formation of linear chains. One of the phenyl rings is disordered over two sites with equal occupancies.

Related literature

For details of the crystal structure of dicyclohexylammonium bis(chlorodifluoroacetato)cyclohexyldiphenylstannate(IV), see Teo et al. (2008 ). For a review of the structural chemistry of organotin carboxylates, see: Tiekink (1991 , 1994 ).

Experimental

Crystal data

(C₁₂H₂₄N)[Sn(C₅H₉)(C₆H₅)₂(C₂ClF₂O₂)]
M_r = 783.27
Monoclinic, P 2₁
a = 8.8610 (2) Å
b = 19.3132 (3) Å
c = 10.6823 (2) Å
β = 109.385 (1)°
V = 1724.47 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.95 mm⁻¹
T = 100 (2) K
0.30 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.679, T_max = 0.870
18017 measured reflections
7831 independent reflections
6637 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.132
S = 1.04
7831 reflections
421 parameters
41 restraints
H-atom parameters constrained
Δρ_max = 1.11 e Å⁻³
Δρ_min = −0.71 e Å⁻³
Absolute structure: Flack (1983 ), 3766 Friedel pairs
Flack parameter: −0.03 (3)

Table 1
Selected geometric parameters (Å, °)

Sn1—C1	2.147 (5)
Sn1—C7	2.136 (6)
Sn1—C13	2.117 (6)
Sn1—O1	2.287 (4)
Sn1—O3	2.249 (4)

C1—Sn1—C7	119.2 (2)
C1—Sn1—C13	121.7 (2)
C1—Sn1—O1	91.3 (2)
C1—Sn1—O3	90.9 (2)
C7—Sn1—C13	118.9 (2)
C7—Sn1—O1	90.6 (2)
C7—Sn1—O3	87.8 (2)
C13—Sn1—O1	82.8 (3)
C13—Sn1—O3	96.5 (3)
O1—Sn1—O3	177.7 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2	0.88	1.88	2.758 (6)	173
N1—H1N2⋯O4ⁱ	0.88	1.93	2.804 (6)	169
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808010775/lh2611sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808010775/lh2611Isup2.hkl

checkCIF report

Comment top

The preceding study reports the crystal structure of dicyclohexylammonium bis(chlorodifluroacetato)cyclohexyldiphenylstannate (Teo et al., 2008).

Replacing the cyclohexyl ligand on tin by the cyclopentyl ligand furnishes a similar stannate compound(I), (Fig. 1). The cation engages in hydrogen bonding to the anion to give rise to a chain structure.

Related literature top

For details of the crystal structure of dicyclohexylammonium bis(chlorodifluoroacetato)cyclohexyldiphenylstannate, see Teo et al. (2008). For a review of the structural chemistry of organotin carboxylates, see: Tiekink (1991, 1994).

Experimental top

Cyclopentyldiphenyltin hydroxide (0.36 g, 1 mmol) was added to an ethanol solution (50 ml) of dicyclohexylamine (0.20 ml, 2 mmol) and chlorodifluoroacetic acid (0.1 ml, 2 mmol). The solution was heated to dissolve the reactants completely; the filtered solution yielded the salt in 70% yield.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: 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).

Figures top

Fig. 1. 50% Probability thermal ellipsoid plot of the two independent formula units of [(C₆H₁₁)₂NH₂)] [Sn(C₅H₉)(C₆H₅)₂(O₂CClF₂)₂]. Hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.

Dicyclohexylammonium bis(chlorodifluoroacetato-κO)cyclopentylhexyldiphenylstannate(IV)] top

Crystal data top

(C₁₂H₂₄N)[Sn(C₅H₉)(C₆H₅)₂(C₂ClF₂O₂)]	F(000) = 800
M_r = 783.27	D_x = 1.508 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4999 reflections
a = 8.8610 (2) Å	θ = 2.3–24.4°
b = 19.3132 (3) Å	µ = 0.95 mm⁻¹
c = 10.6823 (2) Å	T = 100 K
β = 109.385 (1)°	Irregular block, colorless
V = 1724.47 (6) Å³	0.30 × 0.20 × 0.15 mm
Z = 2

Data collection top

Bruker SMART APEX diffractometer	7831 independent reflections
Radiation source: fine-focus sealed tube	6637 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
T_min = 0.679, T_max = 0.870	k = −25→25
18017 measured reflections	l = −13→13

Refinement top

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)] = 0.050	H-atom parameters constrained
wR(F²) = 0.132	w = 1/[σ²(F_o²) + (0.0717P)² + 1.4264P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
7831 reflections	Δρ_max = 1.11 e Å⁻³
421 parameters	Δρ_min = −0.71 e Å⁻³
41 restraints	Absolute structure: Flack (1983), 3766 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.03 (3)

Crystal data top

(C₁₂H₂₄N)[Sn(C₅H₉)(C₆H₅)₂(C₂ClF₂O₂)]	V = 1724.47 (6) Å³
M_r = 783.27	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 8.8610 (2) Å	µ = 0.95 mm⁻¹
b = 19.3132 (3) Å	T = 100 K
c = 10.6823 (2) Å	0.30 × 0.20 × 0.15 mm
β = 109.385 (1)°

Data collection top

Bruker SMART APEX diffractometer	7831 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	6637 reflections with I > 2σ(I)
T_min = 0.679, T_max = 0.870	R_int = 0.038
18017 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.132	Δρ_max = 1.11 e Å⁻³
S = 1.04	Δρ_min = −0.71 e Å⁻³
7831 reflections	Absolute structure: Flack (1983), 3766 Friedel pairs
421 parameters	Absolute structure parameter: −0.03 (3)
41 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sn1	0.41483 (4)	0.50001 (7)	0.27785 (3)	0.03273 (11)
Cl1	0.5652 (5)	0.7213 (2)	0.0894 (3)	0.1213 (13)
Cl2	0.1779 (5)	0.25792 (18)	0.2051 (3)	0.1310 (16)
F1	0.7544 (5)	0.7106 (2)	0.3078 (5)	0.0684 (13)
F2	0.5523 (5)	0.7777 (2)	0.2839 (5)	0.0622 (12)
F3	0.3331 (6)	0.2399 (2)	0.4277 (5)	0.0721 (14)
F4	0.1352 (6)	0.3071 (3)	0.4035 (6)	0.0776 (15)
O1	0.5515 (5)	0.5970 (2)	0.2551 (5)	0.0389 (10)
O2	0.4078 (5)	0.6683 (2)	0.3391 (5)	0.0372 (10)
O3	0.2746 (5)	0.4049 (2)	0.2913 (4)	0.0366 (9)
O4	0.4990 (6)	0.3475 (2)	0.4043 (5)	0.0419 (10)
N1	0.2491 (6)	0.7638 (2)	0.4417 (4)	0.0264 (9)
H1N1	0.2976	0.7356	0.4026	0.032*
H1N2	0.3196	0.7947	0.4861	0.032*
C1	0.5036 (5)	0.5092 (2)	0.4901 (5)	0.0335 (12)
C2	0.445 (4)	0.4703 (16)	0.574 (4)	0.034 (3)	0.50
H2	0.3604	0.4389	0.5336	0.040*	0.50
C3	0.502 (6)	0.474 (2)	0.711 (4)	0.040 (5)	0.50
H3	0.4581	0.4462	0.7645	0.047*	0.50
C4	0.625 (6)	0.520 (3)	0.7657 (10)	0.0475 (18)	0.50
H4	0.6666	0.5237	0.8597	0.057*	0.50
C5	0.693 (5)	0.561 (2)	0.692 (4)	0.037 (4)	0.50
H5	0.7779	0.5926	0.7332	0.045*	0.50
C6	0.6282 (18)	0.5547 (12)	0.555 (4)	0.033 (3)	0.50
H6	0.6714	0.5826	0.5018	0.039*	0.50
C2'	0.420 (4)	0.4798 (14)	0.567 (4)	0.034 (3)	0.50
H2'	0.3212	0.4565	0.5261	0.040*	0.50
C3'	0.484 (6)	0.486 (2)	0.703 (4)	0.040 (5)	0.50
H3'	0.4279	0.4657	0.7564	0.047*	0.50
C4'	0.627 (6)	0.519 (3)	0.7660 (10)	0.0475 (18)	0.50
H4'	0.6697	0.5224	0.8599	0.057*	0.50
C5'	0.707 (5)	0.548 (2)	0.686 (4)	0.037 (4)	0.50
H5'	0.8061	0.5706	0.7278	0.045*	0.50
C6'	0.6483 (16)	0.5438 (12)	0.549 (4)	0.033 (3)	0.50
H6'	0.7046	0.5640	0.4959	0.039*	0.50
C7	0.1931 (7)	0.5482 (3)	0.1691 (6)	0.0315 (12)
C8	0.1848 (8)	0.5921 (3)	0.0642 (6)	0.0373 (13)
H8	0.2746	0.5977	0.0355	0.045*
C9	0.0415 (8)	0.6283 (4)	0.0009 (7)	0.0447 (15)
H9	0.0348	0.6580	−0.0718	0.054*
C10	−0.0874 (8)	0.6213 (3)	0.0426 (6)	0.0409 (14)
H10	−0.1823	0.6469	0.0000	0.049*
C11	−0.0815 (7)	0.5781 (3)	0.1447 (7)	0.0373 (13)
H11	−0.1720	0.5731	0.1728	0.045*
C12	0.0584 (7)	0.5410 (3)	0.2081 (6)	0.0340 (12)
H12	0.0619	0.5105	0.2788	0.041*
C13	0.5521 (7)	0.4533 (4)	0.1721 (7)	0.056 (2)
H13	0.5677	0.4912	0.1139	0.068*
C14	0.4920 (7)	0.3925 (4)	0.0773 (8)	0.062 (2)
H14A	0.4110	0.4081	−0.0064	0.075*
H14B	0.4437	0.3565	0.1182	0.075*
C15	0.6441 (9)	0.3636 (4)	0.0507 (7)	0.074 (3)
H15A	0.6432	0.3123	0.0501	0.089*
H15B	0.6480	0.3802	−0.0358	0.089*
C16	0.7884 (7)	0.3909 (4)	0.1650 (7)	0.0494 (17)
H16A	0.8564	0.4204	0.1297	0.059*
H16B	0.8539	0.3519	0.2142	0.059*
C17	0.7225 (7)	0.4334 (4)	0.2575 (6)	0.0433 (15)
H17A	0.7215	0.4054	0.3348	0.052*
H17B	0.7883	0.4753	0.2898	0.052*
C18	0.5096 (7)	0.6545 (3)	0.2852 (6)	0.0358 (13)
C19	0.5981 (7)	0.7165 (3)	0.2514 (6)	0.0458 (16)
C20	0.3529 (8)	0.3533 (3)	0.3501 (7)	0.0358 (14)
C21	0.2525 (7)	0.2913 (3)	0.3561 (5)	0.0415 (14)
C22	0.1928 (7)	0.7229 (3)	0.5380 (6)	0.0306 (12)
H22	0.1109	0.7509	0.5611	0.037*
C23	0.3314 (9)	0.7076 (3)	0.6660 (6)	0.0437 (15)
H23A	0.4127	0.6786	0.6458	0.052*
H23B	0.3830	0.7514	0.7063	0.052*
C24	0.2667 (10)	0.6697 (4)	0.7623 (7)	0.0514 (18)
H24A	0.1915	0.7003	0.7870	0.062*
H24B	0.3563	0.6585	0.8441	0.062*
C25	0.1806 (9)	0.6031 (3)	0.7024 (7)	0.0423 (15)
H25A	0.2590	0.5698	0.6893	0.051*
H25B	0.1325	0.5820	0.7648	0.051*
C26	0.0522 (8)	0.6162 (3)	0.5720 (7)	0.0433 (15)
H26A	−0.0349	0.6433	0.5874	0.052*
H26B	0.0069	0.5714	0.5318	0.052*
C27	0.1156 (8)	0.6560 (3)	0.4746 (6)	0.0361 (13)
H27A	0.1950	0.6272	0.4514	0.043*
H27B	0.0263	0.6662	0.3920	0.043*
C29	0.1158 (7)	0.8005 (3)	0.3367 (6)	0.0317 (12)
H29	0.0177	0.7711	0.3160	0.038*
C30	0.1550 (8)	0.8094 (4)	0.2104 (7)	0.0463 (16)
H30A	0.1732	0.7635	0.1766	0.056*
H30B	0.2541	0.8370	0.2286	0.056*
C31	0.0151 (9)	0.8464 (5)	0.1056 (8)	0.061 (2)
H31A	0.0441	0.8545	0.0249	0.074*
H31B	−0.0802	0.8160	0.0809	0.074*
C32	−0.0264 (9)	0.9144 (4)	0.1539 (8)	0.057 (2)
H32A	−0.1222	0.9340	0.0862	0.069*
H32B	0.0632	0.9473	0.1667	0.069*
C33	−0.0591 (9)	0.9056 (4)	0.2842 (8)	0.057 (2)
H33A	−0.1579	0.8780	0.2686	0.069*
H33B	−0.0765	0.9517	0.3178	0.069*
C34	0.0797 (9)	0.8696 (4)	0.3879 (7)	0.0471 (16)
H34A	0.1758	0.8994	0.4106	0.057*
H34B	0.0525	0.8622	0.4696	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01949 (15)	0.02969 (16)	0.0492 (2)	0.0012 (2)	0.01167 (12)	−0.0076 (2)
Cl1	0.153 (4)	0.124 (3)	0.103 (2)	−0.027 (2)	0.065 (2)	−0.0111 (19)
Cl2	0.164 (3)	0.085 (2)	0.0910 (19)	−0.061 (2)	−0.029 (2)	0.0079 (15)
F1	0.031 (2)	0.050 (2)	0.128 (4)	−0.0105 (18)	0.031 (2)	0.006 (2)
F2	0.045 (3)	0.035 (2)	0.115 (4)	−0.0008 (18)	0.037 (3)	0.002 (2)
F3	0.062 (3)	0.057 (3)	0.110 (4)	0.019 (2)	0.045 (3)	0.048 (3)
F4	0.049 (3)	0.063 (3)	0.134 (5)	0.010 (2)	0.049 (3)	0.024 (3)
O1	0.021 (2)	0.045 (2)	0.058 (3)	−0.0021 (18)	0.022 (2)	−0.004 (2)
O2	0.027 (2)	0.040 (2)	0.050 (3)	−0.0052 (19)	0.020 (2)	−0.010 (2)
O3	0.024 (2)	0.0246 (19)	0.053 (3)	0.0051 (16)	0.0032 (18)	−0.0040 (17)
O4	0.031 (2)	0.039 (2)	0.054 (3)	0.0095 (19)	0.013 (2)	−0.0006 (19)
N1	0.021 (2)	0.029 (2)	0.031 (2)	−0.0031 (18)	0.0116 (19)	−0.0055 (17)
C1	0.020 (2)	0.027 (3)	0.052 (3)	0.006 (2)	0.011 (2)	0.001 (2)
C2	0.011 (8)	0.037 (7)	0.049 (5)	0.011 (5)	0.007 (6)	−0.012 (4)
C3	0.029 (9)	0.038 (14)	0.054 (5)	0.010 (8)	0.016 (5)	−0.005 (5)
C4	0.043 (4)	0.053 (5)	0.046 (3)	0.007 (3)	0.013 (3)	−0.012 (3)
C5	0.029 (6)	0.023 (13)	0.053 (5)	0.008 (8)	0.003 (5)	−0.018 (7)
C6	0.024 (4)	0.019 (6)	0.054 (5)	0.008 (5)	0.012 (5)	−0.009 (6)
C2'	0.011 (8)	0.037 (7)	0.049 (5)	0.011 (5)	0.007 (6)	−0.012 (4)
C3'	0.029 (9)	0.038 (14)	0.054 (5)	0.010 (8)	0.016 (5)	−0.005 (5)
C4'	0.043 (4)	0.053 (5)	0.046 (3)	0.007 (3)	0.013 (3)	−0.012 (3)
C5'	0.029 (6)	0.023 (13)	0.053 (5)	0.008 (8)	0.003 (5)	−0.018 (7)
C6'	0.024 (4)	0.019 (6)	0.054 (5)	0.008 (5)	0.012 (5)	−0.009 (6)
C7	0.028 (3)	0.022 (2)	0.042 (3)	0.005 (2)	0.009 (2)	−0.007 (2)
C8	0.032 (3)	0.047 (3)	0.036 (3)	−0.006 (3)	0.016 (3)	−0.001 (2)
C9	0.038 (4)	0.053 (4)	0.040 (4)	0.002 (3)	0.010 (3)	0.004 (3)
C10	0.030 (3)	0.039 (3)	0.046 (4)	0.006 (3)	0.003 (3)	−0.004 (3)
C11	0.023 (3)	0.038 (3)	0.053 (4)	−0.001 (2)	0.014 (3)	−0.004 (3)
C12	0.024 (3)	0.033 (3)	0.043 (3)	−0.006 (2)	0.010 (2)	−0.006 (2)
C13	0.028 (3)	0.084 (6)	0.050 (4)	0.015 (4)	0.004 (3)	−0.030 (4)
C14	0.061 (5)	0.066 (5)	0.059 (5)	−0.006 (4)	0.019 (4)	0.005 (4)
C15	0.098 (8)	0.067 (5)	0.070 (6)	0.022 (5)	0.045 (5)	−0.003 (4)
C16	0.039 (4)	0.049 (4)	0.068 (5)	0.013 (3)	0.027 (3)	−0.008 (3)
C17	0.026 (3)	0.059 (4)	0.047 (4)	0.014 (3)	0.015 (3)	−0.004 (3)
C18	0.022 (3)	0.037 (3)	0.046 (3)	−0.005 (2)	0.009 (2)	−0.008 (3)
C19	0.031 (3)	0.049 (4)	0.066 (5)	−0.001 (3)	0.027 (3)	0.005 (3)
C20	0.032 (4)	0.026 (3)	0.050 (4)	0.008 (2)	0.014 (3)	−0.003 (2)
C21	0.035 (3)	0.037 (3)	0.054 (4)	0.005 (3)	0.016 (3)	0.010 (3)
C22	0.032 (3)	0.021 (2)	0.045 (3)	0.001 (2)	0.022 (3)	−0.001 (2)
C23	0.052 (4)	0.042 (3)	0.034 (3)	−0.021 (3)	0.011 (3)	0.000 (3)
C24	0.065 (5)	0.047 (4)	0.047 (4)	−0.019 (3)	0.026 (4)	−0.004 (3)
C25	0.058 (4)	0.025 (3)	0.055 (4)	−0.007 (3)	0.033 (3)	0.002 (3)
C26	0.040 (4)	0.032 (3)	0.064 (4)	−0.009 (3)	0.025 (3)	−0.003 (3)
C27	0.031 (3)	0.030 (3)	0.047 (3)	−0.009 (2)	0.013 (3)	−0.005 (3)
C29	0.023 (3)	0.031 (3)	0.039 (3)	−0.006 (2)	0.008 (2)	0.001 (2)
C30	0.031 (3)	0.066 (5)	0.043 (4)	−0.005 (3)	0.012 (3)	0.008 (3)
C31	0.034 (4)	0.093 (6)	0.050 (4)	−0.012 (4)	0.004 (3)	0.025 (4)
C32	0.034 (4)	0.050 (4)	0.073 (5)	−0.010 (3)	−0.003 (3)	0.030 (4)
C33	0.046 (5)	0.043 (4)	0.075 (5)	0.011 (3)	0.009 (4)	0.011 (3)
C34	0.041 (4)	0.043 (4)	0.055 (4)	0.008 (3)	0.014 (3)	0.003 (3)

Geometric parameters (Å, º) top

Sn1—C1	2.147 (5)	C12—H12	0.9500
Sn1—C7	2.136 (6)	C13—C14	1.527 (7)
Sn1—C13	2.117 (6)	C13—C17	1.530 (7)
Sn1—O1	2.287 (4)	C13—H13	1.0000
Sn1—O3	2.249 (4)	C14—C15	1.569 (7)
Cl1—C19	1.660 (6)	C14—H14A	0.9900
Cl2—C21	1.657 (6)	C14—H14B	0.9900
F1—C19	1.319 (6)	C15—C16	1.539 (7)
F2—C19	1.331 (6)	C15—H15A	0.9900
F3—C21	1.311 (6)	C15—H15B	0.9900
F4—C21	1.334 (6)	C16—C17	1.541 (6)
O1—C18	1.246 (7)	C16—H16A	0.9900
O2—C18	1.249 (7)	C16—H16B	0.9900
O3—C20	1.257 (7)	C17—H17A	0.9900
O4—C20	1.235 (8)	C17—H17B	0.9900
N1—C29	1.508 (7)	C18—C19	1.540 (9)
N1—C22	1.508 (7)	C20—C21	1.506 (9)
N1—H1N1	0.8800	C22—C27	1.512 (8)
N1—H1N2	0.8800	C22—C23	1.534 (9)
C1—C2	1.391 (9)	C22—H22	1.0000
C1—C2'	1.394 (9)	C23—C24	1.522 (9)
C1—C6'	1.396 (9)	C23—H23A	0.9900
C1—C6	1.401 (9)	C23—H23B	0.9900
C2—C3	1.387 (9)	C24—C25	1.524 (9)
C2—H2	0.9500	C24—H24A	0.9900
C3—C4	1.383 (9)	C24—H24B	0.9900
C3—H3	0.9500	C25—C26	1.499 (10)
C4—C5	1.388 (9)	C25—H25A	0.9900
C4—H4	0.9500	C25—H25B	0.9900
C5—C6	1.393 (9)	C26—C27	1.542 (9)
C5—H5	0.9500	C26—H26A	0.9900
C6—H6	0.9500	C26—H26B	0.9900
C2'—C3'	1.386 (9)	C27—H27A	0.9900
C2'—H2'	0.9500	C27—H27B	0.9900
C3'—C4'	1.382 (9)	C29—C30	1.510 (8)
C3'—H3'	0.9500	C29—C34	1.516 (9)
C4'—C5'	1.387 (9)	C29—H29	1.0000
C4'—H4'	0.9500	C30—C31	1.543 (10)
C5'—C6'	1.393 (9)	C30—H30A	0.9900
C5'—H5'	0.9500	C30—H30B	0.9900
C6'—H6'	0.9500	C31—C32	1.499 (12)
C7—C8	1.388 (9)	C31—H31A	0.9900
C7—C12	1.396 (8)	C31—H31B	0.9900
C8—C9	1.410 (9)	C32—C33	1.523 (11)
C8—H8	0.9500	C32—H32A	0.9900
C9—C10	1.365 (10)	C32—H32B	0.9900
C9—H9	0.9500	C33—C34	1.523 (10)
C10—C11	1.361 (9)	C33—H33A	0.9900
C10—H10	0.9500	C33—H33B	0.9900
C11—C12	1.396 (9)	C34—H34A	0.9900
C11—H11	0.9500	C34—H34B	0.9900

C1—Sn1—C7	119.2 (2)	C13—C17—C16	105.1 (4)
C1—Sn1—C13	121.7 (2)	C13—C17—H17A	110.7
C1—Sn1—O1	91.3 (2)	C16—C17—H17A	110.7
C1—Sn1—O3	90.9 (2)	C13—C17—H17B	110.7
C7—Sn1—C13	118.9 (2)	C16—C17—H17B	110.7
C7—Sn1—O1	90.6 (2)	H17A—C17—H17B	108.8
C7—Sn1—O3	87.8 (2)	O1—C18—O2	129.2 (6)
C13—Sn1—O1	82.8 (3)	O1—C18—C19	114.5 (5)
C13—Sn1—O3	96.5 (3)	O2—C18—C19	116.3 (5)
O1—Sn1—O3	177.7 (2)	F1—C19—F2	108.8 (5)
C18—O1—Sn1	119.3 (4)	F1—C19—C18	111.3 (5)
C20—O3—Sn1	117.0 (4)	F2—C19—C18	114.0 (5)
C29—N1—C22	113.5 (4)	F1—C19—Cl1	106.0 (4)
C29—N1—H1N1	108.9	F2—C19—Cl1	105.0 (5)
C29—N1—H1N1	108.9	C18—C19—Cl1	111.2 (5)
C22—N1—H1N2	108.9	O4—C20—O3	128.7 (6)
C22—N1—H1N2	108.9	O4—C20—C21	116.7 (5)
H1N1—N1—H1N2	107.7	O3—C20—C21	114.6 (6)
C2'—C1—C6'	121 (3)	F3—C21—F4	107.1 (5)
C2—C1—C6	115 (3)	F3—C21—C20	114.3 (5)
C2—C1—Sn1	123.3 (19)	F4—C21—C20	112.3 (5)
C2'—C1—Sn1	120.4 (18)	F3—C21—Cl2	103.7 (5)
C6'—C1—Sn1	118 (2)	F4—C21—Cl2	110.4 (5)
C6—C1—Sn1	122 (2)	C20—C21—Cl2	108.6 (4)
C3—C2—C1	125 (3)	N1—C22—C27	110.2 (5)
C3—C2—H2	117.5	N1—C22—C23	111.1 (5)
C1—C2—H2	117.5	C27—C22—C23	110.1 (5)
C4—C3—C2	116 (3)	N1—C22—H22	108.4
C4—C3—H3	122.1	C27—C22—H22	108.4
C2—C3—H3	122.1	C23—C22—H22	108.4
C3—C4—C5	124 (3)	C24—C23—C22	109.0 (6)
C3—C4—H4	117.8	C24—C23—H23A	109.9
C5—C4—H4	117.8	C22—C23—H23A	109.9
C4—C5—C6	116 (3)	C24—C23—H23B	109.9
C4—C5—H5	122.0	C22—C23—H23B	109.9
C6—C5—H5	122.0	H23A—C23—H23B	108.3
C5—C6—C1	124 (3)	C23—C24—C25	111.7 (5)
C5—C6—H6	118.0	C23—C24—H24A	109.3
C1—C6—H6	118.0	C25—C24—H24A	109.3
C3'—C2'—C1	118 (3)	C23—C24—H24B	109.3
C3'—C2'—H2'	120.9	C25—C24—H24B	109.3
C1—C2'—H2'	120.9	H24A—C24—H24B	107.9
C4'—C3'—C2'	122 (3)	C26—C25—C24	111.5 (5)
C4'—C3'—H3'	118.8	C26—C25—H25A	109.3
C2'—C3'—H3'	118.8	C24—C25—H25A	109.3
C3'—C4'—C5'	118 (3)	C26—C25—H25B	109.3
C3'—C4'—H4'	121.2	C24—C25—H25B	109.3
C5'—C4'—H4'	121.2	H25A—C25—H25B	108.0
C4'—C5'—C6'	123 (3)	C25—C26—C27	112.1 (5)
C4'—C5'—H5'	118.7	C25—C26—H26A	109.2
C6'—C5'—H5'	118.7	C27—C26—H26A	109.2
C5'—C6'—C1	118 (3)	C25—C26—H26B	109.2
C5'—C6'—H6'	121.2	C27—C26—H26B	109.2
C1—C6'—H6'	121.2	H26A—C26—H26B	107.9
C8—C7—C12	118.7 (5)	C22—C27—C26	109.6 (5)
C8—C7—Sn1	119.9 (4)	C22—C27—H27A	109.8
C12—C7—Sn1	121.2 (4)	C26—C27—H27A	109.8
C7—C8—C9	119.3 (6)	C22—C27—H27B	109.8
C7—C8—H8	120.4	C26—C27—H27B	109.8
C9—C8—H8	120.4	H27A—C27—H27B	108.2
C10—C9—C8	120.8 (6)	N1—C29—C30	111.2 (5)
C10—C9—H9	119.6	N1—C29—C34	110.6 (5)
C8—C9—H9	119.6	C30—C29—C34	111.2 (5)
C11—C10—C9	120.6 (6)	N1—C29—H29	107.9
C11—C10—H10	119.7	C30—C29—H29	107.9
C9—C10—H10	119.7	C34—C29—H29	107.9
C10—C11—C12	119.7 (6)	C29—C30—C31	109.5 (6)
C10—C11—H11	120.1	C29—C30—H30A	109.8
C12—C11—H11	120.1	C31—C30—H30A	109.8
C7—C12—C11	120.9 (6)	C29—C30—H30B	109.8
C7—C12—H12	119.5	C31—C30—H30B	109.8
C11—C12—H12	119.5	H30A—C30—H30B	108.2
C14—C13—C17	105.1 (5)	C32—C31—C30	112.7 (7)
C14—C13—Sn1	123.1 (5)	C32—C31—H31A	109.1
C17—C13—Sn1	114.6 (4)	C30—C31—H31A	109.1
C14—C13—H13	104.0	C32—C31—H31B	109.1
C17—C13—H13	104.0	C30—C31—H31B	109.1
Sn1—C13—H13	104.0	H31A—C31—H31B	107.8
C13—C14—C15	105.2 (5)	C31—C32—C33	111.1 (6)
C13—C14—H14A	110.7	C31—C32—H32A	109.4
C15—C14—H14A	110.7	C33—C32—H32A	109.4
C13—C14—H14B	110.7	C31—C32—H32B	109.4
C15—C14—H14B	110.7	C33—C32—H32B	109.4
H14A—C14—H14B	108.8	H32A—C32—H32B	108.0
C16—C15—C14	105.8 (4)	C32—C33—C34	111.3 (6)
C16—C15—H15A	110.6	C32—C33—H33A	109.4
C14—C15—H15A	110.6	C34—C33—H33A	109.4
C16—C15—H15B	110.6	C32—C33—H33B	109.4
C14—C15—H15B	110.6	C34—C33—H33B	109.4
H15A—C15—H15B	108.7	H33A—C33—H33B	108.0
C15—C16—C17	107.4 (4)	C29—C34—C33	110.9 (6)
C15—C16—H16A	110.2	C29—C34—H34A	109.5
C17—C16—H16A	110.2	C33—C34—H34A	109.5
C15—C16—H16B	110.2	C29—C34—H34B	109.5
C17—C16—H16B	110.2	C33—C34—H34B	109.5
H16A—C16—H16B	108.5	H34A—C34—H34B	108.1

C13—Sn1—O1—C18	169.9 (5)	C8—C9—C10—C11	−1.3 (10)
C7—Sn1—O1—C18	50.8 (5)	C9—C10—C11—C12	0.6 (10)
C1—Sn1—O1—C18	−68.4 (5)	C8—C7—C12—C11	−1.0 (9)
C13—Sn1—O3—C20	60.0 (5)	Sn1—C7—C12—C11	173.6 (4)
C7—Sn1—O3—C20	178.9 (5)	C10—C11—C12—C7	0.6 (9)
C1—Sn1—O3—C20	−62.0 (5)	C7—Sn1—C13—C14	−61.9 (8)
C13—Sn1—C1—C2	−108.5 (13)	C1—Sn1—C13—C14	124.4 (6)
C7—Sn1—C1—C2	77.8 (13)	O3—Sn1—C13—C14	29.2 (7)
O3—Sn1—C1—C2	−10.2 (13)	O1—Sn1—C13—C14	−148.5 (7)
O1—Sn1—C1—C2	169.2 (13)	C7—Sn1—C13—C17	168.2 (5)
C13—Sn1—C1—C2'	−121.7 (13)	C1—Sn1—C13—C17	−5.5 (7)
C7—Sn1—C1—C2'	64.6 (13)	O3—Sn1—C13—C17	−100.6 (6)
O3—Sn1—C1—C2'	−23.5 (13)	O1—Sn1—C13—C17	81.6 (6)
O1—Sn1—C1—C2'	155.9 (13)	C17—C13—C14—C15	−32.5 (8)
C13—Sn1—C1—C6'	56.8 (11)	Sn1—C13—C14—C15	−166.2 (6)
C7—Sn1—C1—C6'	−116.9 (11)	C13—C14—C15—C16	19.2 (9)
O3—Sn1—C1—C6'	155.1 (11)	C14—C15—C16—C17	1.1 (9)
O1—Sn1—C1—C6'	−25.5 (11)	C14—C13—C17—C16	33.2 (8)
C13—Sn1—C1—C6	70.4 (11)	Sn1—C13—C17—C16	171.5 (5)
C7—Sn1—C1—C6	−103.4 (11)	C15—C16—C17—C13	−21.0 (8)
O3—Sn1—C1—C6	168.6 (11)	Sn1—O1—C18—O2	6.9 (9)
O1—Sn1—C1—C6	−12.0 (11)	Sn1—O1—C18—C19	−173.6 (4)
C2'—C1—C2—C3	−102 (18)	O1—C18—C19—F1	−56.4 (7)
C6'—C1—C2—C3	13.2 (19)	O2—C18—C19—F1	123.1 (6)
C6—C1—C2—C3	−0.2 (3)	O1—C18—C19—F2	180.0 (5)
Sn1—C1—C2—C3	178.7 (11)	O2—C18—C19—F2	−0.5 (8)
C1—C2—C3—C4	0.0 (3)	O1—C18—C19—Cl1	61.5 (6)
C2—C3—C4—C5	0.0 (7)	O2—C18—C19—Cl1	−118.9 (5)
C3—C4—C5—C6	0.2 (9)	Sn1—O3—C20—O4	1.0 (9)
C4—C5—C6—C1	−0.5 (9)	Sn1—O3—C20—C21	179.9 (4)
C2—C1—C6—C5	0.5 (7)	O4—C20—C21—F3	4.9 (8)
C2'—C1—C6—C5	13 (2)	O3—C20—C21—F3	−174.1 (6)
C6'—C1—C6—C5	−102 (19)	O4—C20—C21—F4	127.2 (6)
Sn1—C1—C6—C5	−178.4 (12)	O3—C20—C21—F4	−51.8 (7)
C2—C1—C2'—C3'	70 (18)	O4—C20—C21—Cl2	−110.4 (6)
C6'—C1—C2'—C3'	−0.2 (3)	O3—C20—C21—Cl2	70.6 (6)
C6—C1—C2'—C3'	−13 (2)	C29—N1—C22—C27	76.9 (6)
Sn1—C1—C2'—C3'	178.3 (11)	C29—N1—C22—C23	−160.8 (5)
C1—C2'—C3'—C4'	0.0 (3)	N1—C22—C23—C24	177.0 (5)
C2'—C3'—C4'—C5'	0.0 (6)	C27—C22—C23—C24	−60.6 (7)
C3'—C4'—C5'—C6'	0.2 (8)	C22—C23—C24—C25	57.4 (8)
C4'—C5'—C6'—C1	−0.5 (8)	C23—C24—C25—C26	−54.2 (9)
C2—C1—C6'—C5'	−12 (3)	C24—C25—C26—C27	53.0 (7)
C2'—C1—C6'—C5'	0.5 (6)	N1—C22—C27—C26	−177.6 (5)
C6—C1—C6'—C5'	72 (18)	C23—C22—C27—C26	59.5 (7)
Sn1—C1—C6'—C5'	−178.1 (11)	C25—C26—C27—C22	−56.0 (7)
C13—Sn1—C7—C8	−46.3 (6)	C22—N1—C29—C30	−151.5 (5)
C1—Sn1—C7—C8	127.6 (4)	C22—N1—C29—C34	84.5 (6)
O3—Sn1—C7—C8	−142.5 (5)	N1—C29—C30—C31	179.5 (6)
O1—Sn1—C7—C8	35.8 (5)	C34—C29—C30—C31	−56.8 (7)
C13—Sn1—C7—C12	139.2 (5)	C29—C30—C31—C32	55.6 (8)
C1—Sn1—C7—C12	−46.9 (5)	C30—C31—C32—C33	−54.3 (8)
O3—Sn1—C7—C12	42.9 (4)	C31—C32—C33—C34	54.0 (9)
O1—Sn1—C7—C12	−138.8 (4)	N1—C29—C34—C33	−177.8 (5)
C12—C7—C8—C9	0.3 (9)	C30—C29—C34—C33	58.1 (8)
Sn1—C7—C8—C9	−174.4 (5)	C32—C33—C34—C29	−55.9 (8)
C7—C8—C9—C10	0.9 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2	0.88	1.88	2.758 (6)	173
N1—H1N2···O4ⁱ	0.88	1.93	2.804 (6)	169

Symmetry code: (i) −x+1, y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	(C₁₂H₂₄N)[Sn(C₅H₉)(C₆H₅)₂(C₂ClF₂O₂)]
M_r	783.27
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	8.8610 (2), 19.3132 (3), 10.6823 (2)
β (°)	109.385 (1)
V (Å³)	1724.47 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.95
Crystal size (mm)	0.30 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.679, 0.870
No. of measured, independent and observed [I > 2σ(I)] reflections	18017, 7831, 6637
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.132, 1.04
No. of reflections	7831
No. of parameters	421
No. of restraints	41
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.11, −0.71
Absolute structure	Flack (1983), 3766 Friedel pairs
Absolute structure parameter	−0.03 (3)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Selected geometric parameters (Å, º) top

Sn1—C1	2.147 (5)	Sn1—O1	2.287 (4)
Sn1—C7	2.136 (6)	Sn1—O3	2.249 (4)
Sn1—C13	2.117 (6)

C1—Sn1—C7	119.2 (2)	C7—Sn1—O1	90.6 (2)
C1—Sn1—C13	121.7 (2)	C7—Sn1—O3	87.8 (2)
C1—Sn1—O1	91.3 (2)	C13—Sn1—O1	82.8 (3)
C1—Sn1—O3	90.9 (2)	C13—Sn1—O3	96.5 (3)
C7—Sn1—C13	118.9 (2)	O1—Sn1—O3	177.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2	0.88	1.88	2.758 (6)	173
N1—H1N2···O4ⁱ	0.88	1.93	2.804 (6)	169

Symmetry code: (i) −x+1, y+1/2, −z+1.

Acknowledgements

The authors thank the University of Malaya for funding this study (grant No. SF022155/2007A) and also for 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
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
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Volume 64| Part 5| May 2008| Page m700

doi:10.1107/S1600536808010775

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di­cyclo­hexyl­ammonium bis­­(chloro­di­fluoro­acetato-κO)cyclo­pentyl­di­phenyl­stannate(IV)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Dicyclohexylammonium bis(chlorodifluoroacetato-κO)cyclopentyldiphenylstannate(IV)