Trimethyl­phenyl­ammonium dibromidotriphenyl­stannate(IV)

Yap, Q.L.; Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536809019722

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m714

doi:10.1107/S1600536809019722

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Trimethylphenylammonium dibromidotriphenylstannate(IV)

Quai Ling Yap,^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 19 May 2009; accepted 25 May 2009; online 6 June 2009)

The five-coordinate Sn atom in the title salt, [(CH₃)₃(C₆H₆)N][SnBr₂(C₆H₅)₃], exists in a distorted trans-C₃SnBr₂ trigonal-bipyramidal coordination geometry. In the crystal structure no obvious hydrogen bonding is observed.

Related literature

The are few examples of dihalogenotriarylstannate salts having a counter-ion that does not participate in hydrogen bonding, which appears to assist in stabilizing the salt, see: Beckmann et al. (2002 ); Harrison et al. (1978 ); Kuhn et al. (2001 ); Ng (1995 ); Wharf & Simard (1991 ).

Experimental

Crystal data

(C₉H₁₄N)[SnBr₂(C₆H₅)₃]
M_r = 646.02
Monoclinic, P 2₁
a = 9.0010 (1) Å
b = 16.7778 (2) Å
c = 9.2448 (1) Å
β = 111.003 (1)°
V = 1303.37 (3) Å³
Z = 2
Mo Kα radiation
μ = 4.06 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.567, T_max = 0.746 (expected range = 0.337–0.444)
12525 measured reflections
5966 independent reflections
5889 reflections with I > 2σ(I)
R_int = 0.012

Refinement

R[F² > 2σ(F²)] = 0.016
wR(F²) = 0.042
S = 1.06
5966 reflections
280 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Absolute structure: Flack (1983 ), 2872 Friedel pairs
Flack parameter: 0.011 (3)

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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809019722/tk2456sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809019722/tk2456Isup2.hkl

checkCIF report

Related literature top

The are few examples of dihalogenotriarylstannate salts having a counter-ion that does not participate in hydrogen bonding, which appears to assist in stabilizing the salt, see: Beckmann et al. (2002); Harrison et al. (1978); Kuhn et al. (2001); Ng (1995); Wharf & Simard (1991).

Experimental top

Bis(4-dimethylaminopyridinium) dibromidotriphenylstannate (1.0 g, 1.6 mmol) and trimethylphenylammonium bromide (0.34 g, 1.6 mmol) were heated in ethanol for 1 hour. Colorless crystals separated after a few days.

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: pubCIF (Westrip, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of [PhMe3N][SnBr₂Ph₃] at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Trimethylphenylammonium dibromidotriphenylstannate(IV) top

Crystal data top

(C₉H₁₄N)[SnBr₂(C₆H₅)₃]	F(000) = 636
M_r = 646.02	D_x = 1.646 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 9930 reflections
a = 9.0010 (1) Å	θ = 2.4–28.3°
b = 16.7778 (2) Å	µ = 4.06 mm⁻¹
c = 9.2448 (1) Å	T = 100 K
β = 111.003 (1)°	Block, colorless
V = 1303.37 (3) Å³	0.30 × 0.25 × 0.20 mm
Z = 2

Data collection top

Bruker SMART APEX diffractometer	5966 independent reflections
Radiation source: fine-focus sealed tube	5889 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.012
ω scans	θ_max = 27.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.567, T_max = 0.746	k = −21→21
12525 measured reflections	l = −12→12

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)] = 0.016	H-atom parameters constrained
wR(F²) = 0.042	w = 1/[σ²(F_o²) + (0.0283P)² + 0.211P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
5966 reflections	Δρ_max = 0.38 e Å⁻³
280 parameters	Δρ_min = −0.22 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2872 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.011 (3)

Crystal data top

(C₉H₁₄N)[SnBr₂(C₆H₅)₃]	V = 1303.37 (3) Å³
M_r = 646.02	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.0010 (1) Å	µ = 4.06 mm⁻¹
b = 16.7778 (2) Å	T = 100 K
c = 9.2448 (1) Å	0.30 × 0.25 × 0.20 mm
β = 111.003 (1)°

Data collection top

Bruker SMART APEX diffractometer	5966 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5889 reflections with I > 2σ(I)
T_min = 0.567, T_max = 0.746	R_int = 0.012
12525 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.016	H-atom parameters constrained
wR(F²) = 0.042	Δρ_max = 0.38 e Å⁻³
S = 1.06	Δρ_min = −0.22 e Å⁻³
5966 reflections	Absolute structure: Flack (1983), 2872 Friedel pairs
280 parameters	Absolute structure parameter: 0.011 (3)
1 restraint

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

	x	y	z	U_iso*/U_eq
Sn1	0.800735 (16)	0.499537 (6)	0.968485 (15)	0.01425 (4)
Br1	0.50474 (2)	0.441885 (12)	0.78666 (2)	0.01891 (5)
Br2	1.10719 (2)	0.544697 (12)	1.14791 (2)	0.01839 (5)
N1	0.4280 (2)	0.36054 (11)	1.3067 (2)	0.0184 (3)
C1	0.8550 (2)	0.52187 (12)	0.7653 (2)	0.0173 (4)
C2	0.7539 (3)	0.56900 (13)	0.6462 (3)	0.0213 (4)
H2	0.6596	0.5903	0.6549	0.026*
C3	0.7901 (3)	0.58504 (15)	0.5146 (3)	0.0254 (5)
H3	0.7209	0.6175	0.4346	0.030*
C4	0.9258 (3)	0.55404 (16)	0.4999 (3)	0.0273 (5)
H4	0.9495	0.5649	0.4097	0.033*
C5	1.0273 (3)	0.50715 (18)	0.6166 (3)	0.0292 (5)
H5	1.1205	0.4855	0.6060	0.035*
C6	0.9933 (3)	0.49146 (15)	0.7499 (3)	0.0250 (5)
H6	1.0645	0.4600	0.8304	0.030*
C7	0.8524 (2)	0.38465 (13)	1.0804 (2)	0.0157 (4)
C8	0.8729 (3)	0.37779 (14)	1.2360 (3)	0.0220 (4)
H8	0.8638	0.4235	1.2931	0.026*
C9	0.9068 (3)	0.30373 (16)	1.3081 (3)	0.0301 (5)
H9	0.9167	0.2985	1.4135	0.036*
C10	0.9261 (3)	0.23781 (15)	1.2269 (3)	0.0315 (6)
H10	0.9494	0.1873	1.2764	0.038*
C11	0.9113 (3)	0.24555 (14)	1.0730 (3)	0.0299 (5)
H11	0.9264	0.2005	1.0176	0.036*
C12	0.8743 (3)	0.31912 (14)	0.9998 (3)	0.0249 (5)
H12	0.8641	0.3243	0.8944	0.030*
C13	0.6992 (2)	0.59342 (13)	1.0628 (2)	0.0159 (4)
C14	0.7844 (3)	0.66346 (13)	1.1201 (2)	0.0202 (4)
H14	0.8905	0.6686	1.1227	0.024*
C15	0.7154 (3)	0.72562 (13)	1.1732 (3)	0.0229 (4)
H15	0.7747	0.7728	1.2120	0.027*
C16	0.5604 (3)	0.71924 (14)	1.1700 (3)	0.0253 (5)
H16	0.5126	0.7622	1.2041	0.030*
C17	0.4761 (3)	0.64944 (15)	1.1163 (3)	0.0250 (5)
H17	0.3710	0.6441	1.1161	0.030*
C18	0.5447 (2)	0.58699 (13)	1.0626 (2)	0.0186 (4)
H18	0.4855	0.5396	1.0256	0.022*
C19	0.5292 (2)	0.28835 (13)	1.3666 (2)	0.0175 (4)
C20	0.6100 (3)	0.28234 (14)	1.5255 (3)	0.0238 (5)
H20	0.6051	0.3244	1.5924	0.029*
C21	0.6975 (3)	0.21445 (15)	1.5849 (3)	0.0264 (5)
H21	0.7536	0.2100	1.6933	0.032*
C22	0.7040 (3)	0.15287 (14)	1.4874 (3)	0.0242 (4)
H22	0.7628	0.1059	1.5290	0.029*
C23	0.6246 (3)	0.15991 (13)	1.3294 (3)	0.0227 (4)
H23	0.6302	0.1179	1.2626	0.027*
C24	0.5367 (3)	0.22799 (13)	1.2673 (3)	0.0206 (4)
H24	0.4826	0.2330	1.1586	0.025*
C25	0.2875 (3)	0.35662 (15)	1.3594 (3)	0.0265 (5)
H25A	0.3257	0.3534	1.4727	0.040*
H25B	0.2234	0.3094	1.3147	0.040*
H25C	0.2221	0.4046	1.3249	0.040*
C26	0.3650 (3)	0.36554 (15)	1.1328 (3)	0.0317 (6)
H26A	0.4542	0.3686	1.0958	0.048*
H26B	0.2985	0.4132	1.0997	0.048*
H26C	0.3012	0.3180	1.0894	0.048*
C27	0.5184 (3)	0.43595 (14)	1.3676 (3)	0.0246 (4)
H27A	0.6096	0.4394	1.3336	0.037*
H27B	0.5563	0.4358	1.4810	0.037*
H27C	0.4484	0.4819	1.3278	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01733 (6)	0.01231 (6)	0.01367 (6)	0.00070 (5)	0.00626 (4)	0.00004 (5)
Br1	0.01852 (9)	0.01789 (10)	0.01856 (10)	−0.00257 (7)	0.00452 (8)	−0.00274 (8)
Br2	0.01643 (9)	0.01616 (10)	0.01963 (10)	−0.00018 (7)	0.00289 (7)	−0.00003 (8)
N1	0.0194 (8)	0.0184 (9)	0.0166 (8)	0.0022 (7)	0.0056 (7)	0.0002 (7)
C1	0.0205 (9)	0.0167 (10)	0.0149 (9)	−0.0030 (7)	0.0064 (7)	−0.0023 (7)
C2	0.0207 (10)	0.0206 (10)	0.0219 (10)	−0.0020 (8)	0.0069 (8)	0.0007 (8)
C3	0.0246 (11)	0.0295 (12)	0.0183 (10)	−0.0072 (9)	0.0030 (8)	0.0035 (9)
C4	0.0313 (12)	0.0360 (13)	0.0164 (10)	−0.0127 (10)	0.0107 (9)	−0.0040 (9)
C5	0.0279 (11)	0.0385 (13)	0.0262 (11)	0.0014 (11)	0.0157 (9)	−0.0030 (11)
C6	0.0255 (10)	0.0293 (13)	0.0206 (10)	0.0051 (9)	0.0087 (8)	0.0017 (9)
C7	0.0108 (8)	0.0177 (9)	0.0160 (9)	0.0051 (7)	0.0014 (7)	0.0017 (8)
C8	0.0217 (10)	0.0222 (11)	0.0248 (11)	0.0014 (8)	0.0114 (9)	0.0022 (9)
C9	0.0276 (12)	0.0338 (13)	0.0323 (13)	0.0033 (10)	0.0148 (10)	0.0152 (11)
C10	0.0212 (10)	0.0212 (11)	0.0508 (16)	0.0022 (9)	0.0113 (11)	0.0155 (11)
C11	0.0252 (11)	0.0155 (10)	0.0466 (15)	0.0006 (9)	0.0101 (11)	−0.0062 (11)
C12	0.0246 (11)	0.0203 (11)	0.0264 (11)	−0.0016 (8)	0.0048 (9)	−0.0052 (9)
C13	0.0192 (9)	0.0152 (9)	0.0130 (8)	0.0030 (7)	0.0054 (7)	0.0030 (8)
C14	0.0229 (10)	0.0178 (10)	0.0197 (10)	−0.0006 (8)	0.0072 (8)	0.0007 (8)
C15	0.0329 (12)	0.0143 (10)	0.0213 (10)	−0.0016 (8)	0.0095 (9)	−0.0023 (8)
C16	0.0344 (12)	0.0202 (11)	0.0259 (11)	0.0079 (9)	0.0165 (10)	0.0015 (9)
C17	0.0263 (11)	0.0261 (11)	0.0270 (11)	0.0056 (9)	0.0150 (9)	0.0026 (9)
C18	0.0212 (9)	0.0176 (10)	0.0181 (9)	0.0003 (8)	0.0082 (8)	0.0013 (8)
C19	0.0155 (9)	0.0171 (10)	0.0198 (10)	0.0017 (7)	0.0061 (8)	0.0029 (8)
C20	0.0291 (11)	0.0254 (11)	0.0193 (11)	0.0052 (9)	0.0114 (9)	−0.0007 (9)
C21	0.0307 (12)	0.0310 (13)	0.0183 (10)	0.0081 (10)	0.0096 (9)	0.0039 (9)
C22	0.0240 (10)	0.0217 (11)	0.0273 (11)	0.0068 (8)	0.0099 (9)	0.0046 (9)
C23	0.0244 (10)	0.0167 (10)	0.0276 (11)	0.0001 (8)	0.0099 (9)	−0.0028 (9)
C24	0.0211 (10)	0.0184 (10)	0.0192 (10)	−0.0003 (8)	0.0034 (8)	−0.0011 (8)
C25	0.0165 (10)	0.0271 (12)	0.0373 (13)	0.0025 (9)	0.0115 (9)	0.0040 (10)
C26	0.0450 (14)	0.0278 (13)	0.0158 (10)	0.0150 (10)	0.0029 (10)	0.0027 (9)
C27	0.0257 (10)	0.0174 (10)	0.0304 (11)	−0.0012 (8)	0.0094 (9)	0.0006 (9)

Geometric parameters (Å, º) top

Sn1—Br1	2.7657 (2)	C13—C18	1.395 (3)
Sn1—Br2	2.7667 (2)	C13—C14	1.399 (3)
Sn1—C1	2.137 (2)	C14—C15	1.390 (3)
Sn1—C7	2.158 (2)	C14—H14	0.9500
Sn1—C13	2.156 (2)	C15—C16	1.389 (3)
N1—C27	1.500 (3)	C15—H15	0.9500
N1—C26	1.503 (3)	C16—C17	1.387 (4)
N1—C19	1.497 (3)	C16—H16	0.9500
N1—C25	1.511 (3)	C17—C18	1.394 (3)
C1—C2	1.396 (3)	C17—H17	0.9500
C1—C6	1.399 (3)	C18—H18	0.9500
C2—C3	1.394 (3)	C19—C24	1.385 (3)
C2—H2	0.9500	C19—C20	1.390 (3)
C3—C4	1.378 (4)	C20—C21	1.382 (3)
C3—H3	0.9500	C20—H20	0.9500
C4—C5	1.382 (4)	C21—C22	1.386 (3)
C4—H4	0.9500	C21—H21	0.9500
C5—C6	1.397 (3)	C22—C23	1.382 (3)
C5—H5	0.9500	C22—H22	0.9500
C6—H6	0.9500	C23—C24	1.391 (3)
C7—C12	1.381 (3)	C23—H23	0.9500
C7—C8	1.388 (3)	C24—H24	0.9500
C8—C9	1.391 (3)	C25—H25A	0.9800
C8—H8	0.9500	C25—H25B	0.9800
C9—C10	1.382 (4)	C25—H25C	0.9800
C9—H9	0.9500	C26—H26A	0.9800
C10—C11	1.387 (4)	C26—H26B	0.9800
C10—H10	0.9500	C26—H26C	0.9800
C11—C12	1.389 (3)	C27—H27A	0.9800
C11—H11	0.9500	C27—H27B	0.9800
C12—H12	0.9500	C27—H27C	0.9800

C1—Sn1—C7	120.02 (8)	C18—C13—Sn1	120.68 (16)
C1—Sn1—C13	119.42 (8)	C14—C13—Sn1	120.82 (14)
C7—Sn1—C13	120.54 (7)	C15—C14—C13	120.7 (2)
C1—Sn1—Br2	89.20 (5)	C15—C14—H14	119.7
C13—Sn1—Br2	91.91 (5)	C13—C14—H14	119.7
C7—Sn1—Br2	87.71 (5)	C16—C15—C14	120.5 (2)
C1—Sn1—Br1	90.06 (5)	C16—C15—H15	119.8
C13—Sn1—Br1	92.62 (5)	C14—C15—H15	119.8
C7—Sn1—Br1	88.51 (5)	C15—C16—C17	119.3 (2)
Br1—Sn1—Br2	175.151 (7)	C15—C16—H16	120.4
C27—N1—C26	107.47 (18)	C17—C16—H16	120.4
C27—N1—C19	111.54 (16)	C16—C17—C18	120.5 (2)
C26—N1—C19	112.77 (17)	C16—C17—H17	119.8
C27—N1—C25	108.64 (17)	C18—C17—H17	119.8
C26—N1—C25	107.97 (18)	C17—C18—C13	120.6 (2)
C19—N1—C25	108.32 (17)	C17—C18—H18	119.7
C2—C1—C6	118.6 (2)	C13—C18—H18	119.7
C2—C1—Sn1	120.17 (15)	C24—C19—C20	121.1 (2)
C6—C1—Sn1	121.19 (15)	C24—C19—N1	120.93 (18)
C3—C2—C1	120.5 (2)	C20—C19—N1	117.91 (19)
C3—C2—H2	119.8	C19—C20—C21	119.2 (2)
C1—C2—H2	119.8	C19—C20—H20	120.4
C4—C3—C2	120.4 (2)	C21—C20—H20	120.4
C4—C3—H3	119.8	C22—C21—C20	120.4 (2)
C2—C3—H3	119.8	C22—C21—H21	119.8
C5—C4—C3	120.0 (2)	C20—C21—H21	119.8
C5—C4—H4	120.0	C21—C22—C23	119.8 (2)
C3—C4—H4	120.0	C21—C22—H22	120.1
C4—C5—C6	120.2 (2)	C23—C22—H22	120.1
C4—C5—H5	119.9	C22—C23—C24	120.6 (2)
C6—C5—H5	119.9	C22—C23—H23	119.7
C5—C6—C1	120.4 (2)	C24—C23—H23	119.7
C5—C6—H6	119.8	C19—C24—C23	118.8 (2)
C1—C6—H6	119.8	C19—C24—H24	120.6
C12—C7—C8	120.1 (2)	C23—C24—H24	120.6
C12—C7—Sn1	120.01 (15)	N1—C25—H25A	109.5
C8—C7—Sn1	119.79 (15)	N1—C25—H25B	109.5
C9—C8—C7	119.7 (2)	H25A—C25—H25B	109.5
C9—C8—H8	120.2	N1—C25—H25C	109.5
C7—C8—H8	120.2	H25A—C25—H25C	109.5
C10—C9—C8	120.2 (2)	H25B—C25—H25C	109.5
C10—C9—H9	119.9	N1—C26—H26A	109.5
C8—C9—H9	119.9	N1—C26—H26B	109.5
C9—C10—C11	119.8 (2)	H26A—C26—H26B	109.5
C9—C10—H10	120.1	N1—C26—H26C	109.5
C11—C10—H10	120.1	H26A—C26—H26C	109.5
C12—C11—C10	120.1 (2)	H26B—C26—H26C	109.5
C12—C11—H11	120.0	N1—C27—H27A	109.5
C10—C11—H11	120.0	N1—C27—H27B	109.5
C7—C12—C11	120.0 (2)	H27A—C27—H27B	109.5
C7—C12—H12	120.0	N1—C27—H27C	109.5
C11—C12—H12	120.0	H27A—C27—H27C	109.5
C18—C13—C14	118.46 (19)	H27B—C27—H27C	109.5

C13—Sn1—C1—C2	−38.04 (19)	C10—C11—C12—C7	0.1 (3)
C7—Sn1—C1—C2	143.32 (15)	C1—Sn1—C13—C18	113.96 (16)
Br2—Sn1—C1—C2	−129.79 (16)	C7—Sn1—C13—C18	−67.41 (18)
Br1—Sn1—C1—C2	55.01 (16)	Br2—Sn1—C13—C18	−155.88 (16)
C13—Sn1—C1—C6	140.49 (17)	Br1—Sn1—C13—C18	22.41 (16)
C7—Sn1—C1—C6	−38.1 (2)	C1—Sn1—C13—C14	−63.53 (18)
Br2—Sn1—C1—C6	48.75 (17)	C7—Sn1—C13—C14	115.10 (17)
Br1—Sn1—C1—C6	−126.46 (17)	Br2—Sn1—C13—C14	26.62 (16)
C6—C1—C2—C3	0.2 (3)	Br1—Sn1—C13—C14	−155.09 (16)
Sn1—C1—C2—C3	178.79 (16)	C18—C13—C14—C15	−1.0 (3)
C1—C2—C3—C4	0.5 (3)	Sn1—C13—C14—C15	176.54 (16)
C2—C3—C4—C5	−0.4 (4)	C13—C14—C15—C16	−0.2 (3)
C3—C4—C5—C6	−0.4 (4)	C14—C15—C16—C17	1.4 (3)
C4—C5—C6—C1	1.1 (4)	C15—C16—C17—C18	−1.5 (3)
C2—C1—C6—C5	−1.0 (3)	C16—C17—C18—C13	0.4 (3)
Sn1—C1—C6—C5	−179.56 (19)	C14—C13—C18—C17	0.9 (3)
C1—Sn1—C7—C12	−19.52 (19)	Sn1—C13—C18—C17	−176.66 (16)
C13—Sn1—C7—C12	161.86 (15)	C27—N1—C19—C24	−131.5 (2)
Br2—Sn1—C7—C12	−107.26 (16)	C26—N1—C19—C24	−10.4 (3)
Br1—Sn1—C7—C12	69.69 (16)	C25—N1—C19—C24	109.0 (2)
C1—Sn1—C7—C8	156.62 (15)	C27—N1—C19—C20	51.2 (2)
C13—Sn1—C7—C8	−22.00 (19)	C26—N1—C19—C20	172.2 (2)
Br2—Sn1—C7—C8	68.87 (15)	C25—N1—C19—C20	−68.3 (2)
Br1—Sn1—C7—C8	−114.17 (15)	C24—C19—C20—C21	−0.8 (3)
C12—C7—C8—C9	−3.6 (3)	N1—C19—C20—C21	176.6 (2)
Sn1—C7—C8—C9	−179.74 (16)	C19—C20—C21—C22	−0.4 (4)
C7—C8—C9—C10	2.5 (3)	C20—C21—C22—C23	1.1 (4)
C8—C9—C10—C11	−0.1 (3)	C21—C22—C23—C24	−0.7 (4)
C9—C10—C11—C12	−1.2 (4)	C20—C19—C24—C23	1.1 (3)
C8—C7—C12—C11	2.3 (3)	N1—C19—C24—C23	−176.13 (19)
Sn1—C7—C12—C11	178.46 (17)	C22—C23—C24—C19	−0.4 (3)

Experimental details

Crystal data
Chemical formula	(C₉H₁₄N)[SnBr₂(C₆H₅)₃]
M_r	646.02
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	9.0010 (1), 16.7778 (2), 9.2448 (1)
β (°)	111.003 (1)
V (Å³)	1303.37 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.06
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.567, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	12525, 5966, 5889
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.016, 0.042, 1.06
No. of reflections	5966
No. of parameters	280
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.22
Absolute structure	Flack (1983), 2872 Friedel pairs
Absolute structure parameter	0.011 (3)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), pubCIF (Westrip, 2009).

Acknowledgements

We thank the University of Malaya (RG020/09AFR) for supporting this study.

References

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