Tris(N,N-di­methyl­anilinium) hexa­bromido­stannate(IV) bromide

Chouaib, H.; Kamoun, S.; Ayedi, H.F.

doi:10.1107/S1600536813012403

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page m311

doi:10.1107/S1600536813012403

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Tris(N,N-dimethylanilinium) hexabromidostannate(IV) bromide

Hassen Chouaib,^a ^* Slaheddine Kamoun ^a and Hassine Ferid Ayedi ^a

^aLaboratoire de Génie des Matériaux et Environnement, École Nationale d'Ingénieurs de Sfax, BP 1173, Sfax, Tunisia
^*Correspondence e-mail: chouaib.hassen@yahoo.fr

(Received 25 April 2013; accepted 6 May 2013; online 11 May 2013)

In the title compound, (C₈H₁₂N)₃[SnBr₆]Br, the anilinium N atom of one of the three unique cations exhibits flip-flop disorder with an 0.60:0.40 occupancy ratio. In the crystal, N—H⋯Br hydrogen bonds link the N,N-dimethylanilinium cations and both Br⁻ anions and [SnBr₆]²⁻ dianions into a layered arrangement parallel to (001).

Related literature

For related structures, see: Ali et al. (2008 ), Al-Far et al. (2009 ); Howie et al. (2009 ). For electric, magnetic and dielectric properties of related compounds, see: Hiraga et al. (2007 ); Karoui et al. (2013 ).

Experimental

Crystal data

(C₈H₁₂N)₃[SnBr₆]Br
M_r = 1044.62
Monoclinic, P 2₁ /c
a = 14.3408 (6) Å
b = 9.1904 (4) Å
c = 26.4029 (12) Å
β = 93.451 (2)°
V = 3473.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 8.81 mm⁻¹
T = 296 K
0.10 × 0.10 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ) T_min = 0.415, T_max = 0.431
27006 measured reflections
6112 independent reflections
4555 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.064
S = 1.01
6112 reflections
333 parameters
7 restraints
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H1⋯Br7ⁱ	0.91	2.38	3.269 (4)	165
N21—H2⋯Br7	0.91	2.30	3.196 (4)	168
N31B—H3B⋯Br5	0.91	2.74	3.631 (8)	167.1
N31A—H3A⋯Br4ⁱⁱ	0.83	2.56	3.352 (13)	159.7
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: WinGX (Farrugia, 2012 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813012403/nk2205sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813012403/nk2205Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813012403/nk2205Isup3.cdx

checkCIF report

Comment top

Research in the field of organic-inorganic hybrid compounds is of great interest, because of their special magnetic (Hiraga et al., 2007) and electronic (Karoui et al., 2013) properties. The influence of the different organic cations is expected to affect the packing and then the specific properties. The title crystal structure contains three N,N-dimethylanilinium cations, one bromide ion and one isolated SnBr6 dianions, Fig.1. Each Sn site is surrounded by six Br ligands forming a distorted [SnBr₆]^2- octahedron with Sn—Br bond lengths ranging from 2.5767 (6) Å to 2.6217 (6) Å. The relatively high values of C—N distances (> 1.5 Å) are due to the disorder of the nitrogen atom N(31). The π-π interactions between phenyl rings may be neglected (>4 Å); in fact the shortest distances between the centroids of the rings are: Cg2 ··· Cg1ⁱ = 4.784 (4) Å; Cg1 ··· Cg3ⁱⁱ = 4.993 (4) Å, Cg3 ··· Cg2ⁱⁱ = 5.140 (3) Å (Cg1, Cg2 and Cg3 are the centroids of the C12–C16 and C21–C26 rings, C31—C36 rings, respectively; symmetry codes: (i) x,-1 + y,z; (ii)-x, 0.5 + y, 0.5 - z). The major contributions to the cohesion and the stability of the structure is the presence of N—H···Br hydrogen bonds which provide a linkage between N,N-dimethylanilinium cations and both Br- anions and [SnBr₆]^2- dianions which include four relatively medium contacts, with H···Br and N..Br distances ranging from 2.30 Å to 2.74 Å and 3.196 (4) Å to 3.631 (8) Å, respectively (Fig. 2 and Table 1).

Related literature top

For related structures, see: Ali et al. (2008), Al-Far et al. (2009); Howie et al. (2009). For electric, magnetic and dielectric properties of related compounds, see: Hiraga et al. (2007); Karoui et al. (2013),

Experimental top

The title compound was prepared by refluxing during 5 h a solution of metallic tin (3 g, 25 mmol) in 40 ml an aqueous solution of hydrobromic acid, HBr 47%. To this solution, 9.5 ml (75 mmol) of a solution of N,N-dimethylaniline was added at reflux temperature. After a slow solvent evaporation yellow crystals suitable for X-ray analysis were obtained. They were washed with diethyl ether and dried over P₂O₅.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. A view of the asymmetric unit of the title compound . Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal packing of the title compound showing the hydrogen bonding network as red dashed lines.

Tris(N,N-dimethylanilinium) hexabromidostannate(IV) bromide top

Crystal data top

(C₈H₁₂N)₃[SnBr₆]Br	F(000) = 1984
M_r = 1044.62	Cell parameters from 57951 reflections
Monoclinic, P2₁/c	D_x = 1.998 Mg m⁻³ D_m = 2.009 Mg m⁻³ D_m measured by Flotation
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.3408 (6) Å	Cell parameters from 57951 reflections
b = 9.1904 (4) Å	θ = 1.6–25.0°
c = 26.4029 (12) Å	µ = 8.81 mm⁻¹
β = 93.451 (2)°	T = 296 K
V = 3473.5 (3) Å³	Cube, yellow
Z = 4	0.10 × 0.10 × 0.10 mm

Data collection top

Bruker APEXII CCD diffractometer	6112 independent reflections
Radiation source: fine-focus sealed tube	4555 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −16→17
T_min = 0.415, T_max = 0.431	k = −10→10
27006 measured reflections	l = −31→31

Refinement top

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.064	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.020P)² + 4.9952P] where P = (F_o² + 2F_c²)/3
6112 reflections	(Δ/σ)_max = 0.001
333 parameters	Δρ_max = 0.55 e Å⁻³
7 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

(C₈H₁₂N)₃[SnBr₆]Br	V = 3473.5 (3) Å³
M_r = 1044.62	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.3408 (6) Å	µ = 8.81 mm⁻¹
b = 9.1904 (4) Å	T = 296 K
c = 26.4029 (12) Å	0.10 × 0.10 × 0.10 mm
β = 93.451 (2)°

Data collection top

Bruker APEXII CCD diffractometer	6112 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	4555 reflections with I > 2σ(I)
T_min = 0.415, T_max = 0.431	R_int = 0.044
27006 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	7 restraints
wR(F²) = 0.064	H-atom parameters constrained
S = 1.01	Δρ_max = 0.55 e Å⁻³
6112 reflections	Δρ_min = −0.38 e Å⁻³
333 parameters

Special details top

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

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sn1	0.34886 (2)	0.42038 (3)	0.357239 (11)	0.03803 (9)
Br1	0.51100 (3)	0.36489 (6)	0.32373 (2)	0.05700 (15)
Br2	0.27708 (3)	0.21753 (5)	0.297717 (19)	0.05008 (13)
Br3	0.18550 (3)	0.47638 (6)	0.38796 (2)	0.06065 (15)
Br4	0.42257 (4)	0.62582 (6)	0.415392 (19)	0.06096 (16)
Br5	0.32156 (4)	0.61078 (6)	0.283898 (19)	0.05471 (14)
Br6	0.37920 (4)	0.23426 (6)	0.42947 (2)	0.06195 (15)
Br7	0.05993 (4)	0.72433 (6)	0.48704 (2)	0.06009 (15)
C11	0.8147 (3)	0.4670 (5)	0.40030 (16)	0.0408 (11)
C12	0.9067 (3)	0.4520 (5)	0.38938 (18)	0.0490 (12)
H12	0.9543	0.4607	0.4147	0.059*
C13	0.9264 (4)	0.4237 (6)	0.3399 (2)	0.0600 (14)
H13	0.9882	0.4142	0.3315	0.072*
C14	0.8561 (4)	0.4095 (6)	0.30307 (19)	0.0651 (15)
H14	0.8703	0.3888	0.2699	0.078*
C15	0.7657 (4)	0.4254 (7)	0.3145 (2)	0.0671 (16)
H15	0.7181	0.4172	0.2891	0.080*
C16	0.7444 (3)	0.4537 (6)	0.36346 (19)	0.0575 (14)
H16	0.6825	0.4637	0.3715	0.069*
C17	0.7015 (4)	0.4466 (7)	0.4685 (2)	0.086 (2)
H17A	0.6945	0.4708	0.5035	0.128*
H17B	0.6977	0.3430	0.4643	0.128*
H17C	0.6528	0.4924	0.4477	0.128*
C18	0.8038 (4)	0.6560 (6)	0.4652 (2)	0.0769 (18)
H18A	0.7906	0.6722	0.5000	0.115*
H18B	0.7606	0.7107	0.4435	0.115*
H18C	0.8664	0.6868	0.4599	0.115*
N11	0.7940 (3)	0.4989 (5)	0.45325 (14)	0.0525 (10)
H1	0.8380	0.4517	0.4734	0.063*
C21	0.0426 (3)	0.9402 (5)	0.35440 (17)	0.0438 (11)
C22	0.0362 (4)	1.0562 (6)	0.3223 (2)	0.0590 (14)
H22	0.0750	1.1366	0.3273	0.071*
C23	−0.0299 (4)	1.0508 (7)	0.2821 (2)	0.0689 (16)
H23	−0.0354	1.1288	0.2597	0.083*
C24	−0.0864 (4)	0.9350 (7)	0.2747 (2)	0.0653 (15)
H24	−0.1309	0.9341	0.2475	0.078*
C25	−0.0788 (4)	0.8201 (7)	0.3066 (2)	0.0735 (17)
H25	−0.1179	0.7401	0.3013	0.088*
C26	−0.0128 (4)	0.8212 (6)	0.3471 (2)	0.0634 (15)
H26	−0.0064	0.7418	0.3689	0.076*
C27	0.1164 (5)	1.0776 (6)	0.4274 (2)	0.0774 (18)
H27A	0.1623	1.0696	0.4552	0.116*
H27B	0.0563	1.0964	0.4402	0.116*
H27C	0.1328	1.1562	0.4057	0.116*
C28	0.2073 (4)	0.8948 (6)	0.3829 (2)	0.0707 (16)
H28A	0.2500	0.8944	0.4123	0.106*
H28B	0.2285	0.9626	0.3584	0.106*
H28C	0.2041	0.7992	0.3683	0.106*
N21	0.1128 (3)	0.9387 (4)	0.39786 (15)	0.0509 (10)
H2	0.0942	0.8687	0.4194	0.061*
C32	0.4009 (5)	0.4525 (8)	0.0832 (3)	0.107 (3)
H32	0.4589	0.4171	0.0751	0.128*
C38	0.4210 (4)	0.2539 (6)	0.1905 (2)	0.0648 (15)
C37	0.5277 (4)	0.4612 (7)	0.1808 (3)	0.0710 (17)
C31	0.3753 (4)	0.4520 (7)	0.1324 (3)	0.084 (2)
N31A	0.4589 (7)	0.3584 (11)	0.1545 (4)	0.044 (2)	0.40
C34	0.2539 (5)	0.5579 (7)	0.0589 (3)	0.100 (3)
H34	0.2123	0.5950	0.0338	0.120*
C35	0.2300 (5)	0.5551 (8)	0.1080 (3)	0.100 (2)
H35	0.1719	0.5895	0.1163	0.119*
C36	0.2906 (5)	0.5022 (8)	0.1448 (3)	0.097 (2)
H36	0.2744	0.5003	0.1783	0.117*
C33	0.3390 (6)	0.5064 (9)	0.0464 (3)	0.109 (3)
H33	0.3548	0.5080	0.0128	0.131*
N31B	0.4261 (5)	0.4111 (8)	0.1831 (3)	0.0515 (18)	0.60
H3B	0.4100	0.4645	0.2103	0.13 (5)*	0.60
H3A	0.5006	0.3114	0.1410	0.18 (11)*	0.40
H37A	0.5243	0.5588	0.1673	0.14 (3)*
H37B	0.5753	0.4084	0.1646	0.21 (5)*
H37C	0.5437	0.4663	0.2167	0.15 (3)*
H38A	0.4597	0.1850	0.1747	0.31 (7)*
H38B	0.3564	0.2317	0.1825	0.10 (2)*
H38C	0.4338	0.2541	0.2263	0.29 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.03490 (16)	0.04135 (18)	0.03801 (17)	−0.00518 (14)	0.00366 (13)	0.00125 (14)
Br1	0.0349 (3)	0.0660 (3)	0.0708 (4)	−0.0059 (2)	0.0090 (2)	−0.0079 (3)
Br2	0.0450 (3)	0.0501 (3)	0.0548 (3)	−0.0096 (2)	−0.0002 (2)	−0.0069 (2)
Br3	0.0456 (3)	0.0628 (3)	0.0754 (4)	0.0049 (3)	0.0187 (3)	−0.0003 (3)
Br4	0.0764 (4)	0.0629 (3)	0.0441 (3)	−0.0256 (3)	0.0081 (3)	−0.0089 (3)
Br5	0.0653 (3)	0.0499 (3)	0.0481 (3)	−0.0041 (3)	−0.0039 (2)	0.0104 (2)
Br6	0.0702 (3)	0.0619 (3)	0.0533 (3)	0.0010 (3)	−0.0001 (3)	0.0163 (3)
Br7	0.0630 (3)	0.0667 (4)	0.0504 (3)	0.0031 (3)	0.0019 (2)	0.0128 (3)
C11	0.042 (3)	0.044 (3)	0.036 (2)	−0.002 (2)	−0.002 (2)	0.005 (2)
C12	0.041 (3)	0.057 (3)	0.049 (3)	−0.002 (2)	−0.005 (2)	0.006 (3)
C13	0.051 (3)	0.072 (4)	0.058 (3)	−0.003 (3)	0.014 (3)	0.005 (3)
C14	0.077 (4)	0.079 (4)	0.039 (3)	−0.001 (3)	0.002 (3)	−0.005 (3)
C15	0.061 (4)	0.086 (4)	0.052 (3)	−0.011 (3)	−0.013 (3)	−0.006 (3)
C16	0.045 (3)	0.071 (4)	0.054 (3)	−0.003 (3)	−0.007 (2)	0.000 (3)
C17	0.083 (4)	0.103 (5)	0.075 (4)	−0.012 (4)	0.037 (3)	−0.001 (4)
C18	0.079 (4)	0.072 (4)	0.082 (4)	−0.014 (3)	0.016 (3)	−0.027 (3)
N11	0.048 (2)	0.063 (3)	0.047 (2)	0.009 (2)	0.0001 (19)	0.003 (2)
C21	0.039 (2)	0.049 (3)	0.043 (3)	−0.001 (2)	0.002 (2)	−0.002 (2)
C22	0.059 (3)	0.053 (3)	0.065 (3)	−0.009 (3)	0.003 (3)	0.015 (3)
C23	0.072 (4)	0.070 (4)	0.065 (4)	0.010 (3)	−0.002 (3)	0.022 (3)
C24	0.059 (3)	0.080 (4)	0.055 (3)	0.010 (3)	−0.009 (3)	−0.010 (3)
C25	0.077 (4)	0.066 (4)	0.075 (4)	−0.017 (3)	−0.011 (3)	−0.011 (4)
C26	0.082 (4)	0.045 (3)	0.062 (4)	−0.012 (3)	−0.010 (3)	0.005 (3)
C27	0.100 (5)	0.062 (4)	0.069 (4)	−0.012 (3)	−0.009 (3)	−0.016 (3)
C28	0.049 (3)	0.071 (4)	0.092 (4)	0.003 (3)	0.005 (3)	0.017 (3)
N21	0.057 (3)	0.047 (2)	0.049 (2)	−0.006 (2)	0.001 (2)	0.004 (2)
C32	0.093 (5)	0.083 (5)	0.144 (8)	0.024 (4)	0.010 (6)	0.015 (5)
C38	0.070 (4)	0.055 (4)	0.071 (4)	−0.008 (3)	0.015 (3)	0.018 (3)
C37	0.061 (4)	0.063 (4)	0.087 (5)	−0.015 (3)	−0.014 (3)	0.007 (3)
C31	0.067 (4)	0.080 (5)	0.101 (5)	−0.026 (4)	−0.038 (4)	0.038 (4)
N31A	0.040 (6)	0.045 (6)	0.048 (6)	0.004 (5)	−0.002 (5)	0.006 (5)
C34	0.123 (6)	0.068 (5)	0.101 (6)	0.021 (4)	−0.067 (5)	−0.007 (4)
C35	0.091 (5)	0.098 (6)	0.106 (6)	0.021 (4)	−0.016 (5)	−0.012 (5)
C36	0.101 (6)	0.109 (6)	0.079 (5)	−0.019 (5)	−0.017 (4)	−0.009 (4)
C33	0.161 (8)	0.093 (6)	0.072 (5)	0.023 (6)	−0.005 (5)	−0.005 (4)
N31B	0.049 (4)	0.055 (5)	0.050 (4)	0.005 (4)	−0.001 (4)	−0.005 (4)

Geometric parameters (Å, º) top

Sn1—Br3	2.5767 (6)	C25—H25	0.9300
Sn1—Br6	2.5792 (6)	C26—H26	0.9300
Sn1—Br1	2.5879 (6)	C27—N21	1.495 (6)
Sn1—Br2	2.6096 (6)	C27—H27A	0.9600
Sn1—Br4	2.6161 (6)	C27—H27B	0.9600
Sn1—Br5	2.6217 (6)	C27—H27C	0.9600
C11—C16	1.363 (6)	C28—N21	1.490 (6)
C11—C12	1.375 (6)	C28—H28A	0.9600
C11—N11	1.476 (5)	C28—H28B	0.9600
C12—C13	1.378 (7)	C28—H28C	0.9600
C12—H12	0.9300	N21—H2	0.9100
C13—C14	1.364 (7)	C32—C33	1.370 (7)
C13—H13	0.9300	C32—C31	1.371 (6)
C14—C15	1.357 (7)	C32—H32	0.9300
C14—H14	0.9300	C38—N31B	1.460 (9)
C15—C16	1.371 (7)	C38—N31A	1.478 (11)
C15—H15	0.9300	C38—H38A	0.954
C16—H16	0.9300	C38—H38B	0.960
C17—N11	1.488 (7)	C38—H38C	0.951
C17—H17A	0.9600	C37—N31A	1.507 (11)
C17—H17B	0.9600	C37—N31B	1.532 (9)
C17—H17C	0.9600	C37—H37A	0.966
C18—N11	1.483 (7)	C37—H37B	0.960
C18—H18A	0.9600	C37—H37C	0.962
C18—H18B	0.9600	C31—C36	1.356 (7)
C18—H18C	0.9600	C31—N31B	1.531 (9)
N11—H1	0.9100	C31—N31A	1.560 (12)
C21—C26	1.358 (7)	N31A—N31B	1.034 (12)
C21—C22	1.362 (7)	N31A—H3A	0.834
C21—N21	1.480 (6)	C34—C35	1.361 (7)
C22—C23	1.380 (7)	C34—C33	1.367 (7)
C22—H22	0.9300	C34—H34	0.9300
C23—C24	1.345 (8)	C35—C36	1.354 (7)
C23—H23	0.9300	C35—H35	0.9300
C24—C25	1.351 (8)	C36—H36	0.9300
C24—H24	0.9300	C33—H33	0.9300
C25—C26	1.386 (7)	N31B—H3B	0.912

Br3—Sn1—Br6	90.91 (2)	H27B—C27—H27C	109.5
Br3—Sn1—Br1	178.36 (2)	N21—C28—H28A	109.5
Br6—Sn1—Br1	90.40 (2)	N21—C28—H28B	109.5
Br3—Sn1—Br2	89.948 (19)	H28A—C28—H28B	109.5
Br6—Sn1—Br2	90.82 (2)	N21—C28—H28C	109.5
Br1—Sn1—Br2	89.042 (19)	H28A—C28—H28C	109.5
Br3—Sn1—Br4	90.80 (2)	H28B—C28—H28C	109.5
Br6—Sn1—Br4	90.03 (2)	C21—N21—C28	112.6 (4)
Br1—Sn1—Br4	90.19 (2)	C21—N21—C27	113.4 (4)
Br2—Sn1—Br4	178.86 (2)	C28—N21—C27	111.5 (4)
Br3—Sn1—Br5	90.06 (2)	C21—N21—H2	106.3
Br6—Sn1—Br5	178.87 (2)	C28—N21—H2	106.3
Br1—Sn1—Br5	88.64 (2)	C27—N21—H2	106.3
Br2—Sn1—Br5	89.773 (19)	C33—C32—C31	118.3 (6)
Br4—Sn1—Br5	89.37 (2)	C33—C32—H32	120.9
C16—C11—C12	121.3 (4)	C31—C32—H32	120.9
C16—C11—N11	120.8 (4)	N31B—C38—N31A	41.2 (5)
C12—C11—N11	118.0 (4)	N31B—C38—H38A	124.3
C11—C12—C13	118.2 (4)	N31A—C38—H38A	84.5
C11—C12—H12	120.9	N31B—C38—H38B	103.6
C13—C12—H12	120.9	N31A—C38—H38B	112.5
C14—C13—C12	120.6 (5)	H38A—C38—H38B	109.9
C14—C13—H13	119.7	N31B—C38—H38C	97.1
C12—C13—H13	119.7	N31A—C38—H38C	125.6
C15—C14—C13	120.5 (5)	H38A—C38—H38C	110.7
C15—C14—H14	119.8	H38B—C38—H38C	110.1
C13—C14—H14	119.8	N31A—C37—N31B	39.8 (5)
C14—C15—C16	119.9 (5)	N31A—C37—H37A	113.3
C14—C15—H15	120.0	N31B—C37—H37A	105.5
C16—C15—H15	120.0	N31A—C37—H37B	86.6
C11—C16—C15	119.6 (5)	N31B—C37—H37B	124.7
C11—C16—H16	120.2	H37A—C37—H37B	109.0
C15—C16—H16	120.2	N31A—C37—H37C	126.6
N11—C17—H17A	109.5	N31B—C37—H37C	98.6
N11—C17—H17B	109.5	H37A—C37—H37C	108.9
H17A—C17—H17B	109.5	H37B—C37—H37C	109.3
N11—C17—H17C	109.5	C36—C31—C32	121.5 (6)
H17A—C17—H17C	109.5	C36—C31—N31B	105.0 (7)
H17B—C17—H17C	109.5	C32—C31—N31B	133.4 (7)
N11—C18—H18A	109.5	C36—C31—N31A	140.9 (8)
N11—C18—H18B	109.5	C32—C31—N31A	96.4 (7)
H18A—C18—H18B	109.5	N31B—C31—N31A	39.1 (4)
N11—C18—H18C	109.5	N31B—N31A—C38	68.5 (8)
H18A—C18—H18C	109.5	N31B—N31A—C37	71.5 (8)
H18B—C18—H18C	109.5	C38—N31A—C37	111.4 (8)
C11—N11—C18	111.9 (4)	N31B—N31A—C31	68.9 (8)
C11—N11—C17	115.2 (4)	C38—N31A—C31	107.2 (7)
C18—N11—C17	109.3 (4)	C37—N31A—C31	107.1 (7)
C11—N11—H1	106.6	N31B—N31A—H3A	157.3 (12)
C18—N11—H1	106.6	C38—N31A—H3A	103.8 (9)
C17—N11—H1	106.6	C37—N31A—H3A	93.1 (8)
C26—C21—C22	121.7 (5)	C31—N31A—H3A	133.0 (11)
C26—C21—N21	117.8 (4)	C35—C34—C33	120.2 (6)
C22—C21—N21	120.4 (4)	C35—C34—H34	119.9
C21—C22—C23	117.9 (5)	C33—C34—H34	119.9
C21—C22—H22	121.1	C36—C35—C34	120.1 (7)
C23—C22—H22	121.1	C36—C35—H35	119.9
C24—C23—C22	121.4 (5)	C34—C35—H35	119.9
C24—C23—H23	119.3	C35—C36—C31	119.7 (7)
C22—C23—H23	119.3	C35—C36—H36	120.2
C23—C24—C25	120.1 (5)	C31—C36—H36	120.2
C23—C24—H24	119.9	C34—C33—C32	120.2 (7)
C25—C24—H24	119.9	C34—C33—H33	119.9
C24—C25—C26	120.1 (5)	C32—C33—H33	119.9
C24—C25—H25	119.9	N31A—N31B—C38	70.3 (8)
C26—C25—H25	119.9	N31A—N31B—C31	72.0 (8)
C21—C26—C25	118.8 (5)	C38—N31B—C31	109.6 (6)
C21—C26—H26	120.6	N31A—N31B—C37	68.8 (7)
C25—C26—H26	120.6	C38—N31B—C37	110.9 (6)
N21—C27—H27A	109.5	C31—N31B—C37	107.3 (6)
N21—C27—H27B	109.5	N31A—N31B—H3B	167.5
H27A—C27—H27B	109.5	C38—N31B—H3B	114.1
N21—C27—H27C	109.5	C31—N31B—H3B	115.3
H27A—C27—H27C	109.5	C37—N31B—H3B	98.9

C16—C11—C12—C13	0.3 (7)	C32—C31—N31A—N31B	163.7 (8)
N11—C11—C12—C13	−179.4 (4)	C36—C31—N31A—C38	27.9 (14)
C11—C12—C13—C14	−0.7 (8)	C32—C31—N31A—C38	−138.4 (8)
C12—C13—C14—C15	1.1 (9)	N31B—C31—N31A—C38	58.0 (8)
C13—C14—C15—C16	−1.0 (9)	C36—C31—N31A—C37	−91.7 (11)
C12—C11—C16—C15	−0.3 (8)	C32—C31—N31A—C37	102.0 (8)
N11—C11—C16—C15	179.4 (5)	N31B—C31—N31A—C37	−61.7 (8)
C14—C15—C16—C11	0.6 (9)	C33—C34—C35—C36	0.5 (12)
C16—C11—N11—C18	−97.6 (5)	C34—C35—C36—C31	−0.1 (12)
C12—C11—N11—C18	82.1 (5)	C32—C31—C36—C35	−0.5 (11)
C16—C11—N11—C17	28.1 (7)	N31B—C31—C36—C35	176.5 (7)
C12—C11—N11—C17	−152.2 (5)	N31A—C31—C36—C35	−164.4 (9)
C26—C21—C22—C23	1.0 (8)	C35—C34—C33—C32	−0.4 (12)
N21—C21—C22—C23	179.2 (4)	C31—C32—C33—C34	−0.1 (12)
C21—C22—C23—C24	0.1 (8)	C37—N31A—N31B—C38	−123.1 (5)
C22—C23—C24—C25	−0.7 (9)	C31—N31A—N31B—C38	119.5 (5)
C23—C24—C25—C26	0.1 (9)	C38—N31A—N31B—C31	−119.5 (5)
C22—C21—C26—C25	−1.6 (8)	C37—N31A—N31B—C31	117.5 (5)
N21—C21—C26—C25	−179.8 (5)	C38—N31A—N31B—C37	123.1 (5)
C24—C25—C26—C21	1.0 (9)	C31—N31A—N31B—C37	−117.5 (5)
C26—C21—N21—C28	96.9 (5)	N31A—C38—N31B—C31	61.5 (8)
C22—C21—N21—C28	−81.4 (6)	N31A—C38—N31B—C37	−56.7 (8)
C26—C21—N21—C27	−135.4 (5)	C36—C31—N31B—N31A	160.9 (8)
C22—C21—N21—C27	46.3 (6)	C32—C31—N31B—N31A	−22.6 (11)
C33—C32—C31—C36	0.5 (11)	C36—C31—N31B—C38	100.4 (7)
C33—C32—C31—N31B	−175.4 (7)	C32—C31—N31B—C38	−83.1 (10)
C33—C32—C31—N31A	170.4 (7)	N31A—C31—N31B—C38	−60.5 (8)
N31B—C38—N31A—C37	58.6 (8)	C36—C31—N31B—C37	−139.0 (6)
N31B—C38—N31A—C31	−58.3 (8)	C32—C31—N31B—C37	37.4 (11)
N31B—C37—N31A—C38	−56.9 (8)	N31A—C31—N31B—C37	60.0 (8)
N31B—C37—N31A—C31	60.0 (8)	N31A—C37—N31B—C38	57.6 (8)
C36—C31—N31A—N31B	−30.0 (13)	N31A—C37—N31B—C31	−62.1 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H1···Br7ⁱ	0.91	2.38	3.269 (4)	165
N21—H2···Br7	0.91	2.30	3.196 (4)	168
N31B—H3B···Br5	0.91	2.74	3.631 (8)	167.1
N31A—H3A···Br4ⁱⁱ	0.83	2.56	3.352 (13)	159.7

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	(C₈H₁₂N)₃[SnBr₆]Br
M_r	1044.62
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	14.3408 (6), 9.1904 (4), 26.4029 (12)
β (°)	93.451 (2)
V (Å³)	3473.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	8.81
Crystal size (mm)	0.10 × 0.10 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2006)
T_min, T_max	0.415, 0.431
No. of measured, independent and observed [I > 2σ(I)] reflections	27006, 6112, 4555
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.064, 1.01
No. of reflections	6112
No. of parameters	333
No. of restraints	7
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.38

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H1···Br7ⁱ	0.91	2.38	3.269 (4)	165.1
N21—H2···Br7	0.91	2.30	3.196 (4)	167.9
N31B—H3B···Br5	0.91	2.74	3.631 (8)	167.1
N31A—H3A···Br4ⁱⁱ	0.83	2.56	3.352 (13)	159.7

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y−1/2, −z+1/2.

Acknowledgements

The authors gratefully acknowledge the support of the Tunisian Ministry of Higher Education and Scientific Research.

References

Al-Far, R. H., Haddad, S. F. & Ali, B. F. (2009). Acta Cryst. E65, m583–m584. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Ali, B. F., Al-Far, R. H. & Haddad, S. F. (2008). Acta Cryst. E64, m749–m750. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Hiraga, H., Miyasaka, H., Nakata, K., Kajiwara, T., Takaishi, S., Oshim, Y., Nojiri, H. & Yamashita, M. (2007). Inorg. Chem. 46, 9661–9671. Web of Science CSD CrossRef PubMed CAS Google Scholar
Howie, R. A., Lima, G. M. de, Tiekink, E. R. T., Wardell, J. L. & Wardell, S. M. S. V. (2009). Acta Cryst. E65, m1562. Web of Science CSD CrossRef IUCr Journals Google Scholar
Karoui, S., Kamoun, S. & Jouini, A. (2013). J. Solid State Chem. 197, 60–68. Web of Science CSD CrossRef CAS Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar