catena-Poly[N,N,N′,N′-tetra­methyl­ethylendi­ammonium [[tetra­bromido­antimonate(III)]-μ-bromido] hemihydrate]

Kharrat, H.; Kamoun, S.; Michaud, F.

doi:10.1107/S1600536813028894

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 12| December 2013| Pages m637-m638

doi:10.1107/S1600536813028894

Open

access

catena-Poly[N,N,N′,N′-tetramethylethylendiammonium [[tetrabromidoantimonate(III)]-μ-bromido] hemihydrate]

Houda Kharrat,^a ^* Slaheddine Kamoun ^a and François Michaud ^b

^aLaboratoire de Génie des Matériaux et Environnement, Ecole Nationale d'Ingénieurs de Sfax, Université de Sfax, BP 1173, Sfax, Tunisia, and ^bService commun d'analyse par diffraction des rayons X, Université de Brest, 6 avenue Victor Le Gorgeu, CS 93837, F-29238 Brest Cedex 3, France
^*Correspondence e-mail: kharrat_houda@yahoo.fr

(Received 23 September 2013; accepted 21 October 2013; online 6 November 2013)

The asymmetric unit of the title compound {(C₆H₁₈N₂)₂[Sb₂Br₁₀]·H₂O}_n, consists of two tetramethylethylendiammonium cations that are located on centres of inversion, as well as one tetramethylethylendiammonium cation, one water molecule, one distorted octahedral [SbBr₆]³⁻anion and one bisphenoidal [SbBr₄]⁻ anion in general positions. The [SbBr₆]³⁻ and [SbBr₄]⁻ anions are linked together by two long Sb—Br bonds of 3.2709 (8) and 3.5447 (7) Å into {[Sb₂Br₁₀]⁴⁻}_n chains along [001]. One of the three tetramethylethylendiammonium cations is disordered and was refined using a split model (occupancy ratio 0.58:0.42). The cations and the water molecule are connected to the {[Sb₂Br₁₀]⁴⁻}_n polymeric anions by weak N—H ⋯Br and O(water)—H ⋯Br hydrogen bonding.

CCDC reference: 967628

Related literature

For crystal structures of related organic antimonate(III) halogenides, see: Bujak & Angel (2005 ); Chaabouni et al. (1997 , 1998 ). For a similar structure, see: Owczarek et al. (2012 ). The bond-valence sum was calculated using the parameters given by Brown & Altermatt (1985 ).

Experimental

Crystal data

(C₆H₁₈N₂)[Sb₂Br₁₀]·H₂O
M_r = 1297.06
Orthorhombic, P b c a
a = 18.0860 (4) Å
b = 19.1755 (4) Å
c = 19.4619 (4) Å
V = 6749.5 (2) Å³
Z = 8
Mo Kα radiation
μ = 13.45 mm⁻¹
T = 298 K
0.43 × 0.30 × 0.19 mm

Data collection

Oxford Diffraction Xcalibur Sapphire2 diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrystAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.011, T_max = 0.078
65748 measured reflections
10770 independent reflections
5721 reflections with I > 2σ(I)
R_int = 0.096

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.089
S = 1.01
10770 reflections
290 parameters
15 restraints
H-atom parameters constrained
Δρ_max = 1.92 e Å⁻³
Δρ_min = −1.98 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Br1	0.91	2.59	3.362 (4)	143
N2—H2⋯Br1	0.91	2.56	3.353 (5)	146
N3—H3⋯Br7ⁱ	0.91	2.5	3.352 (4)	157
N4—H4⋯Br3	0.91	2.52	3.318 (4)	147
OW—H1W⋯Br4ⁱⁱ	0.83	3.03	3.759 (7)	148
OW—H2W⋯Br3	0.83	2.67	3.449 (7)	157
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrystAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrystAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 967628

Crystal structure: contains datablock I. DOI: 10.1107/S1600536813028894/nc2318sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813028894/nc2318Isup2.hkl

checkCIF report

Comment top

The structure determination is part of a larger project related to the synthesis, structure and phase transitions in the group of new ferroic crystals of halogenoantimonates (III) with organic cations of various sizes and symmetries (Bujak & Angel, 2005; Chaabouni et al., 1997; Chaabouni et al., 1998). In these compounds the Sb atom shows a tendency toward distorded octahedral coordination with some rather long Sb—X bonds, which is attributed to the aspherical distribution of the lone pair electron (LP) at the Sb(III) cation.

The asymetric unit of the title compound consists of both, [SbBr₆]^3- and [SbBr₄]^- anions, a water molecule and three tetramethylethylene diammonium cations of which two are located on centers of inversion (Fig. 1). One of these cations is disordered and was refined using a split model. The anionic substructure is composed of distordered [Sb(1)Br₆]^3- octahedra that share two trans corners with two others [Sb(2)Br₄]^- anions that shows a saw-horse coordination. These anions are linked into zig zag {[Sb₂Br₁₀]^4-}_n pseudo chains that elongate along the [001] direction (Fig. 2). Two types of Sb—Br distances are present within these chains: eight short Sb—Br (terminal) distances [2.5405 (7) - 2.9906 (7) Å] and two long Sb—Br (bridging) distances [Sb(2)···Br(5) = 3.2709 (8) Å and Sb(2)···Br(6) = 3.5447 (7) Å], all of them are shorter than the sum of the Van der Waals radii (4.1 Å). A similar structural behavior was already reported by Owczarek (Owczarek et al., 2012). By taking into account the sixth-fold coordination of antimony atom, we have proceeded to calculate the bond-valence sum (BVS) of this metal using the parameters given by Brown (Brown & Altermatt, 1985). The BVS calculation of the Sb(1) and Sb(2) ions confirm the presumed oxidation state of Sb (III). The difference between the longest and the shortest Sb—Br distances in the Sb(1)Br₆ and Sb(2)Br₆ units amount to 0.3353 (7) Å and 1.0042 (7) Å. Differences were also found in the Br—Sb—Br angles involving Br atoms that are mutually cis configurated. The differences are 13.79 (2)° for Sb(1)Br6 and 23.50 (2)° for Sb(2)Br6. Taking into account the differences described above the lone pair electron at the Sb(III) cations may be considered as stereochemical active. The [C₆H₁₈N₂]²⁺ cations are located between the inorganic chains with their ammonium group facing the oppositely charged {[Sb₂Br₁₀]^4-}_n polyanions. In the crystal structure the cations, anions and water molecules are linked by weak intermolecular N—H···Br and O(W)—H···Br hydrogen bonding (Table 1).

Related literature top

For crystal structures of related organic antimonate(III) halogenides, see: Bujak & Angel (2005); Chaabouni et al. (1997, 1998). For a similar structure, see: Owczarek et al. (2012). The bond-valence sum was calculated using the parameters given by Brown & Altermatt (1985).

Experimental top

Crystals of the title compound were obtained by dissolving a stoichiometric mixture of antimony (III) oxide Sb₂O₃ (5 g, 17 mmol) and N, N, N', N' - tetramethylethylendiamine (C₆H₁₆N₂) (5 ml, 34 mmol) in 100 ml of a solution of HBr (24%) . The resulting aqueous solution was then kept at room temperature. After several weeks prismatic shaped single crystals of the title compound were obtained by slow evaporation of the solvent at room temperature. They were washed with diethyl ether and dried for 4 h over CaCl₂.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. View of the asymmetric unit of the title compound with labelling and displacement ellipsoids drawn at the 30% probability level. Symmetry codes: (i) x + 1, -y + 2, -z + 1; (ii) -x + 1, -y + 1, -z + 1.
	Fig. 2. View of the anionic substructure of the title compound with labelling and displacement ellipsoids drawn at the 30% probability level. Symmetry codes: (i) -x + 1, y + 0.5, -z + 1.5; (ii) -x + 1, -y + 1, -z + 1.

catena-Poly[N,N,N',N'-tetramethylethylendiammonium [[tetrabromidoantimonate(III)]-µ-bromido] hemihydrate] top

Crystal data top

(C₆H₁₈N₂)[Sb₂Br₁₀]·H₂O	Z = 8
M_r = 1297.06	F(000) = 4784
Orthorhombic, Pbca	D_x = 2.553 Mg m⁻³
Hall symbol: -P 2ac 2ab	Mo Kα radiation, λ = 0.71073 Å
a = 18.0860 (4) Å	µ = 13.45 mm⁻¹
b = 19.1755 (4) Å	T = 298 K
c = 19.4619 (4) Å	Prismatic, axis [1 0 0], yellow
V = 6749.5 (2) Å³	0.43 × 0.30 × 0.19 mm

Data collection top

Oxford Diffraction Xcalibur Sapphire2 diffractometer	10770 independent reflections
Radiation source: sealed X-ray tube	5721 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.096
Detector resolution: 8.3622 pixels mm^-1	θ_max = 31.6°, θ_min = 3.1°
ω scans	h = −25→26
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −28→26
T_min = 0.011, T_max = 0.078	l = −26→28
65748 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.033P)² + 2.8328P] where P = (F_o² + 2F_c²)/3
10770 reflections	(Δ/σ)_max = 0.001
290 parameters	Δρ_max = 1.92 e Å⁻³
15 restraints	Δρ_min = −1.98 e Å⁻³

Crystal data top

(C₆H₁₈N₂)[Sb₂Br₁₀]·H₂O	V = 6749.5 (2) Å³
M_r = 1297.06	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 18.0860 (4) Å	µ = 13.45 mm⁻¹
b = 19.1755 (4) Å	T = 298 K
c = 19.4619 (4) Å	0.43 × 0.30 × 0.19 mm

Data collection top

Oxford Diffraction Xcalibur Sapphire2 diffractometer	10770 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	5721 reflections with I > 2σ(I)
T_min = 0.011, T_max = 0.078	R_int = 0.096
65748 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	15 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.01	Δρ_max = 1.92 e Å⁻³
10770 reflections	Δρ_min = −1.98 e Å⁻³
290 parameters

Special details top

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. CrysAlis RED (Oxford Diffraction, 2009)

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 > 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)
Sb1	0.626802 (19)	0.755771 (18)	0.520272 (17)	0.02825 (9)
Sb2	0.351898 (18)	0.442769 (18)	0.734954 (18)	0.02673 (9)
Br1	0.54458 (4)	0.65129 (3)	0.59658 (3)	0.04546 (16)
Br2	0.70124 (4)	0.85628 (3)	0.45458 (4)	0.05252 (18)
Br3	0.48610 (3)	0.81097 (4)	0.46063 (3)	0.04992 (18)
Br4	0.75101 (4)	0.70887 (4)	0.57645 (3)	0.0591 (2)
Br5	0.59238 (4)	0.83959 (4)	0.64163 (4)	0.0646 (2)
Br6	0.64208 (4)	0.66424 (3)	0.41346 (3)	0.04907 (17)
Br7	0.50362 (3)	0.48013 (3)	0.70652 (3)	0.03898 (15)
Br8	0.21218 (3)	0.41314 (4)	0.76132 (4)	0.0591 (2)
Br9	0.35219 (3)	0.53266 (3)	0.83085 (3)	0.04420 (16)
Br10	0.31213 (3)	0.53122 (3)	0.64461 (3)	0.04336 (16)
N1	0.6426 (2)	0.6779 (3)	0.7410 (2)	0.0377 (12)
H1	0.6259	0.6911	0.6989	0.045*
N2	0.4676 (3)	0.7303 (3)	0.7326 (3)	0.0423 (12)
H2	0.4908	0.7287	0.6911	0.051*
C1	0.6693 (4)	0.6051 (3)	0.7355 (4)	0.061 (2)
H1A	0.6291	0.5753	0.7222	0.091*
H1B	0.6883	0.5902	0.7791	0.091*
H1C	0.7077	0.6026	0.7015	0.091*
C2	0.7034 (4)	0.7249 (4)	0.7603 (4)	0.065 (2)
H2A	0.6851	0.7718	0.7633	0.098*
H2B	0.7416	0.7225	0.7262	0.098*
H2C	0.723	0.711	0.804	0.098*
C3	0.5793 (4)	0.6819 (4)	0.7901 (3)	0.066 (2)
H3A	0.5544	0.6372	0.7883	0.08*	0.58
H3B	0.6004	0.6859	0.8357	0.08*	0.58
H3C	0.5908	0.6497	0.827	0.08*	0.42
H3D	0.5812	0.7282	0.8099	0.08*	0.42
C4A	0.5236 (6)	0.7339 (6)	0.7848 (5)	0.047 (3)	0.58
H4A	0.5486	0.7783	0.7793	0.056*	0.58
H4B	0.4984	0.7356	0.8288	0.056*	0.58
C5A	0.4178 (12)	0.6752 (8)	0.7351 (13)	0.071 (6)	0.58
H5A	0.3847	0.6781	0.6966	0.107*	0.58
H5B	0.3899	0.6776	0.777	0.107*	0.58
H5C	0.4443	0.6319	0.7333	0.107*	0.58
C6A	0.4223 (7)	0.8015 (6)	0.7363 (7)	0.058 (4)	0.58
H6A	0.4559	0.8402	0.7345	0.087*	0.58
H6B	0.3947	0.8032	0.7784	0.087*	0.58
H6C	0.3888	0.8041	0.6981	0.087*	0.58
C4B	0.5103 (7)	0.6709 (6)	0.7744 (6)	0.031 (3)	0.42
H4C	0.4835	0.6626	0.8167	0.037*	0.42
H4D	0.5079	0.6282	0.7476	0.037*	0.42
C5B	0.3998 (18)	0.6842 (15)	0.7092 (19)	0.080 (10)	0.42
H5E	0.417	0.6468	0.6807	0.12*	0.42
H5F	0.3656	0.7125	0.6838	0.12*	0.42
H5G	0.3756	0.6654	0.749	0.12*	0.42
C6B	0.4477 (2)	0.7858 (2)	0.7706 (2)	0.092 (9)	0.42
H6E	0.4911	0.8112	0.784	0.138*	0.42
H6F	0.4219	0.7702	0.8109	0.138*	0.42
H6G	0.4159	0.8154	0.7441	0.138*	0.42
N3	0.4164 (2)	0.5295 (2)	0.4486 (2)	0.0347 (11)
H3	0.4377	0.5133	0.4094	0.042*
C7	0.4592 (3)	0.4993 (3)	0.5075 (3)	0.0318 (13)
H7A	0.4436	0.4515	0.5154	0.038*
H7B	0.4492	0.5259	0.5489	0.038*
C8	0.3390 (3)	0.5050 (4)	0.4484 (3)	0.0513 (18)
H8A	0.3381	0.4551	0.4524	0.077*
H8B	0.3156	0.5187	0.4062	0.077*
H8C	0.313	0.5253	0.4865	0.077*
C9	0.4198 (4)	0.6065 (3)	0.4455 (4)	0.0596 (19)
H9A	0.389	0.6229	0.4087	0.089*
H9B	0.4699	0.6209	0.4376	0.089*
H9C	0.4027	0.6256	0.4882	0.089*
N4	0.4240 (2)	0.9494 (2)	0.5451 (2)	0.0348 (11)
H4	0.4463	0.9071	0.5405	0.042*
C10	0.4578 (3)	0.9977 (3)	0.4958 (3)	0.0373 (14)
H10A	0.4366	1.0437	0.502	0.045*
H10B	0.4464	0.9824	0.4495	0.045*
C11	0.4316 (4)	0.9720 (4)	0.6179 (3)	0.064 (2)
H11A	0.4058	0.9399	0.6472	0.095*
H11B	0.411	1.0178	0.6232	0.095*
H11C	0.483	0.9728	0.6302	0.095*
C12	0.3444 (3)	0.9408 (4)	0.5294 (4)	0.061 (2)
H12A	0.3231	0.9076	0.5605	0.091*
H12B	0.3389	0.9243	0.4831	0.091*
H12C	0.3198	0.9848	0.5343	0.091*
OW	0.3596 (4)	0.7703 (5)	0.5870 (4)	0.159 (3)
H1W	0.3219	0.7677	0.563	0.238*
H2W	0.3989	0.7757	0.566	0.238*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sb1	0.0396 (2)	0.02096 (19)	0.02414 (17)	−0.00123 (16)	0.00398 (16)	−0.00193 (15)
Sb2	0.02741 (18)	0.02436 (19)	0.02841 (18)	0.00197 (15)	−0.00144 (15)	0.00237 (16)
Br1	0.0683 (4)	0.0336 (3)	0.0345 (3)	−0.0137 (3)	0.0033 (3)	−0.0023 (3)
Br2	0.0636 (4)	0.0405 (4)	0.0535 (4)	−0.0205 (3)	0.0045 (3)	0.0098 (3)
Br3	0.0512 (4)	0.0541 (4)	0.0444 (4)	0.0098 (3)	−0.0033 (3)	−0.0109 (3)
Br4	0.0503 (4)	0.0776 (5)	0.0493 (4)	0.0205 (4)	−0.0013 (3)	0.0034 (4)
Br5	0.0788 (5)	0.0500 (4)	0.0650 (5)	−0.0101 (4)	0.0015 (4)	−0.0271 (4)
Br6	0.0785 (5)	0.0318 (3)	0.0369 (3)	−0.0005 (3)	0.0089 (3)	−0.0031 (3)
Br7	0.0333 (3)	0.0463 (4)	0.0373 (3)	−0.0007 (3)	0.0038 (2)	0.0046 (3)
Br8	0.0324 (3)	0.0653 (5)	0.0795 (5)	−0.0106 (3)	0.0040 (3)	0.0040 (4)
Br9	0.0542 (4)	0.0467 (4)	0.0318 (3)	0.0074 (3)	−0.0061 (3)	−0.0070 (3)
Br10	0.0519 (4)	0.0484 (4)	0.0298 (3)	0.0162 (3)	−0.0033 (3)	0.0071 (3)
N1	0.036 (3)	0.050 (3)	0.027 (2)	0.008 (2)	−0.004 (2)	−0.001 (2)
N2	0.033 (3)	0.048 (3)	0.046 (3)	0.008 (2)	0.003 (2)	−0.002 (3)
C1	0.060 (5)	0.045 (4)	0.078 (5)	0.021 (3)	−0.009 (4)	−0.005 (4)
C2	0.067 (5)	0.068 (5)	0.060 (5)	−0.019 (4)	0.001 (4)	−0.008 (4)
C3	0.061 (5)	0.100 (7)	0.038 (4)	0.028 (4)	0.011 (3)	0.012 (4)
C4A	0.048 (7)	0.052 (8)	0.039 (6)	0.019 (6)	0.002 (5)	−0.007 (6)
C5A	0.054 (13)	0.050 (9)	0.11 (2)	−0.011 (8)	0.003 (10)	−0.008 (11)
C6A	0.042 (7)	0.041 (7)	0.092 (10)	0.021 (6)	−0.007 (7)	0.008 (7)
C4B	0.050 (9)	0.015 (7)	0.028 (7)	0.004 (6)	0.002 (6)	−0.008 (6)
C5B	0.041 (15)	0.12 (2)	0.07 (2)	−0.020 (13)	−0.018 (11)	0.002 (16)
C6B	0.056 (14)	0.034 (11)	0.19 (3)	0.023 (10)	0.029 (15)	0.003 (15)
N3	0.036 (3)	0.039 (3)	0.029 (3)	−0.001 (2)	0.003 (2)	−0.006 (2)
C7	0.036 (3)	0.034 (3)	0.025 (3)	−0.004 (3)	0.004 (2)	−0.003 (3)
C8	0.031 (3)	0.073 (5)	0.050 (4)	0.002 (3)	−0.003 (3)	−0.002 (4)
C9	0.073 (5)	0.037 (4)	0.068 (5)	0.009 (3)	−0.012 (4)	0.005 (4)
N4	0.038 (3)	0.028 (3)	0.039 (3)	0.008 (2)	0.006 (2)	−0.001 (2)
C10	0.038 (3)	0.045 (4)	0.029 (3)	−0.002 (3)	−0.003 (3)	0.000 (3)
C11	0.062 (4)	0.100 (6)	0.028 (3)	−0.003 (4)	0.001 (3)	0.006 (4)
C12	0.050 (4)	0.065 (5)	0.067 (5)	−0.010 (4)	0.002 (3)	−0.006 (4)
OW	0.128 (6)	0.243 (10)	0.105 (5)	−0.005 (6)	−0.008 (5)	0.028 (6)

Geometric parameters (Å, º) top

Sb1—Br1	2.9035 (7)	C6A—H6A	0.96
Sb1—Br2	2.6762 (7)	C6A—H6B	0.96
Sb1—Br3	2.9906 (7)	C6A—H6C	0.96
Sb1—Br4	2.6553 (7)	C4B—H4C	0.97
Sb1—Br5	2.9240 (8)	C4B—H4D	0.97
Sb1—Br6	2.7347 (7)	C5B—H5E	0.96
Br5—Sb2ⁱ	3.2709 (8)	C5B—H5F	0.96
Sb2—Br6ⁱⁱ	3.5447 (7)	C5B—H5G	0.96
Sb2—Br7	2.8895 (6)	C6B—H6E	0.96
Sb2—Br8	2.6403 (7)	C6B—H6F	0.96
Sb2—Br9	2.5405 (7)	C6B—H6G	0.96
Sb2—Br10	2.5466 (7)	N3—C8	1.477 (7)
N1—C2	1.471 (7)	N3—C9	1.479 (7)
N1—C1	1.480 (7)	N3—C7	1.500 (6)
N1—C3	1.493 (8)	N3—H3	0.91
N1—H1	0.91	C7—C7ⁱⁱ	1.503 (10)
N2—C6B	1.345 (7)	C7—H7A	0.97
N2—C5A	1.389 (19)	C7—H7B	0.97
N2—C4A	1.437 (10)	C8—H8A	0.96
N2—C5B	1.58 (2)	C8—H8B	0.96
N2—C6A	1.596 (11)	C8—H8C	0.96
N2—C4B	1.598 (13)	C9—H9A	0.96
N2—H2	0.91	C9—H9B	0.96
C1—H1A	0.96	C9—H9C	0.96
C1—H1B	0.96	N4—C10	1.467 (7)
C1—H1C	0.96	N4—C12	1.480 (7)
C2—H2A	0.96	N4—C11	1.487 (7)
C2—H2B	0.96	N4—H4	0.91
C2—H2C	0.96	C10—C10ⁱⁱⁱ	1.537 (10)
C3—C4B	1.302 (13)	C10—H10A	0.97
C3—C4A	1.422 (11)	C10—H10B	0.97
C3—H3A	0.97	C11—H11A	0.96
C3—H3B	0.97	C11—H11B	0.96
C3—H3C	0.97	C11—H11C	0.96
C3—H3D	0.97	C12—H12A	0.96
C4A—H4A	0.97	C12—H12B	0.96
C4A—H4B	0.97	C12—H12C	0.96
C5A—H5A	0.96	OW—H1W	0.828
C5A—H5B	0.96	OW—H2W	0.8264
C5A—H5C	0.96

Br1—Sb1—Br2	177.35 (2)	H3A—C3—H3D	147.2
Br1—Sb1—Br3	90.40 (2)	H3B—C3—H3D	63.1
Br1—Sb1—Br4	89.37 (2)	H3C—C3—H3D	106.3
Br1—Sb1—Br5	81.78 (2)	C3—C4A—N2	121.0 (9)
Br1—Sb1—Br6	89.87 (2)	C3—C4A—H4A	107.1
Br2—Sb1—Br3	89.30 (2)	N2—C4A—H4A	107.1
Br2—Sb1—Br4	90.86 (3)	C3—C4A—H4B	107.1
Br2—Sb1—Br5	95.57 (2)	N2—C4A—H4B	107.1
Br2—Sb1—Br6	92.77 (2)	H4A—C4A—H4B	106.8
Br3—Sb1—Br4	178.37 (2)	N2—C5A—H5A	109.5
Br3—Sb1—Br5	86.43 (2)	N2—C5A—H5B	109.5
Br3—Sb1—Br6	91.03 (2)	H5A—C5A—H5B	109.5
Br4—Sb1—Br5	91.93 (2)	N2—C5A—H5C	109.5
Br4—Sb1—Br6	90.58 (2)	H5A—C5A—H5C	109.5
Br5—Sb1—Br6	171.25 (2)	H5B—C5A—H5C	109.5
Br5^iv—Sb2—Br6ⁱⁱ	103.81 (2)	N2—C6A—H6A	109.5
Br5^iv—Sb2—Br7	89.89 (2)	N2—C6A—H6B	109.5
Br5^iv—Sb2—Br8	91.26 (2)	H6A—C6A—H6B	109.5
Br5^iv—Sb2—Br9	82.55 (2)	N2—C6A—H6C	109.5
Br5^iv—Sb2—Br10	175.44 (2)	H6A—C6A—H6C	109.5
Br6ⁱⁱ—Sb2—Br7	87.61 (2)	H6B—C6A—H6C	109.5
Br6ⁱⁱ—Sb2—Br8	93.62 (2)	C3—C4B—N2	117.8 (10)
Br6ⁱⁱ—Sb2—Br9	172.43 (2)	C3—C4B—H4C	107.9
Br6ⁱⁱ—Sb2—Br10	80.31 (2)	N2—C4B—H4C	107.9
Br7—Sb2—Br8	178.07 (3)	C3—C4B—H4D	107.9
Br7—Sb2—Br9	88.31 (2)	N2—C4B—H4D	107.9
Br7—Sb2—Br10	88.33 (2)	H4C—C4B—H4D	107.2
Br8—Sb2—Br9	90.30 (2)	N2—C5B—H5E	109.5
Br8—Sb2—Br10	90.41 (2)	N2—C5B—H5F	109.5
Br9—Sb2—Br10	93.20 (2)	H5E—C5B—H5F	109.5
Sb2ⁱ—Br5—Sb1	149.32 (3)	N2—C5B—H5G	109.5
Sb2ⁱⁱ—Br6—Sb1	173.75 (3)	H5E—C5B—H5G	109.5
C2—N1—C1	110.7 (5)	H5F—C5B—H5G	109.5
C2—N1—C3	112.2 (5)	N2—C6B—H6E	109.5
C1—N1—C3	110.2 (5)	N2—C6B—H6F	109.5
C2—N1—H1	107.9	H6E—C6B—H6F	109.5
C1—N1—H1	107.9	N2—C6B—H6G	109.5
C3—N1—H1	107.9	H6E—C6B—H6G	109.5
C6B—N2—C5A	114.1 (12)	H6F—C6B—H6G	109.5
C6B—N2—C4A	76.2 (5)	C8—N3—C9	110.9 (5)
C5A—N2—C4A	118.1 (10)	C8—N3—C7	111.6 (4)
C6B—N2—C5B	113.2 (15)	C9—N3—C7	113.3 (4)
C5A—N2—C5B	23.1 (17)	C8—N3—H3	106.9
C4A—N2—C5B	141.2 (13)	C9—N3—H3	106.9
C6B—N2—C6A	32.9 (5)	C7—N3—H3	106.9
C5A—N2—C6A	108.4 (10)	N3—C7—C7ⁱⁱ	110.5 (5)
C4A—N2—C6A	106.8 (7)	N3—C7—H7A	109.6
C5B—N2—C6A	95.3 (13)	C7ⁱⁱ—C7—H7A	109.6
C6B—N2—C4B	114.4 (6)	N3—C7—H7B	109.6
C5A—N2—C4B	75.8 (9)	C7ⁱⁱ—C7—H7B	109.6
C4A—N2—C4B	48.3 (6)	H7A—C7—H7B	108.1
C5B—N2—C4B	97.1 (11)	N3—C8—H8A	109.5
C6A—N2—C4B	146.8 (8)	N3—C8—H8B	109.5
C6B—N2—H2	129.6	H8A—C8—H8B	109.5
C5A—N2—H2	107.7	N3—C8—H8C	109.5
C4A—N2—H2	107.7	H8A—C8—H8C	109.5
C5B—N2—H2	94.8	H8B—C8—H8C	109.5
C6A—N2—H2	107.7	N3—C9—H9A	109.5
C4B—N2—H2	101.8	N3—C9—H9B	109.5
N1—C1—H1A	109.5	H9A—C9—H9B	109.5
N1—C1—H1B	109.5	N3—C9—H9C	109.5
H1A—C1—H1B	109.5	H9A—C9—H9C	109.5
N1—C1—H1C	109.5	H9B—C9—H9C	109.5
H1A—C1—H1C	109.5	C10—N4—C12	109.9 (4)
H1B—C1—H1C	109.5	C10—N4—C11	113.6 (5)
N1—C2—H2A	109.5	C12—N4—C11	108.7 (5)
N1—C2—H2B	109.5	C10—N4—H4	108.2
H2A—C2—H2B	109.5	C12—N4—H4	108.2
N1—C2—H2C	109.5	C11—N4—H4	108.2
H2A—C2—H2C	109.5	N4—C10—C10ⁱⁱⁱ	112.4 (6)
H2B—C2—H2C	109.5	N4—C10—H10A	109.1
C4B—C3—C4A	54.4 (7)	C10ⁱⁱⁱ—C10—H10A	109.1
C4B—C3—N1	125.2 (8)	N4—C10—H10B	109.1
C4A—C3—N1	122.3 (7)	C10ⁱⁱⁱ—C10—H10B	109.1
C4B—C3—H3A	53.3	H10A—C10—H10B	107.9
C4A—C3—H3A	106.8	N4—C11—H11A	109.5
N1—C3—H3A	106.8	N4—C11—H11B	109.5
C4B—C3—H3B	127.2	H11A—C11—H11B	109.5
C4A—C3—H3B	106.8	N4—C11—H11C	109.5
N1—C3—H3B	106.8	H11A—C11—H11C	109.5
H3A—C3—H3B	106.6	H11B—C11—H11C	109.5
C4B—C3—H3C	106	N4—C12—H12A	109.5
C4A—C3—H3C	130.7	N4—C12—H12B	109.5
N1—C3—H3C	106	H12A—C12—H12B	109.5
H3A—C3—H3C	64.1	N4—C12—H12C	109.5
H3B—C3—H3C	44.6	H12A—C12—H12C	109.5
C4B—C3—H3D	106	H12B—C12—H12C	109.5
C4A—C3—H3D	53.9	H1W—OW—H2W	115.9
N1—C3—H3D	106

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+2, −z+1; (iv) −x+1, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Br1	0.91	2.59	3.362 (4)	143
N2—H2···Br1	0.91	2.56	3.353 (5)	146
N3—H3···Br7ⁱⁱ	0.91	2.5	3.352 (4)	157
N4—H4···Br3	0.91	2.52	3.318 (4)	147
OW—H1W···Br4^v	0.83	3.03	3.759 (7)	148
OW—H2W···Br3	0.83	2.67	3.449 (7)	157

Symmetry codes: (ii) −x+1, −y+1, −z+1; (v) x−1/2, −y+3/2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Br1	0.91	2.59	3.362 (4)	143
N2—H2···Br1	0.91	2.56	3.353 (5)	146.4
N3—H3···Br7ⁱ	0.91	2.5	3.352 (4)	157
N4—H4···Br3	0.91	2.52	3.318 (4)	147.2
OW—H1W···Br4ⁱⁱ	0.83	3.03	3.759 (7)	147.5
OW—H2W···Br3	0.83	2.67	3.449 (7)	156.7

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1/2, −y+3/2, −z+1.

Acknowledgements

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

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Brown, I. D. & Altermatt, D. (1985). Acta Cryst. B41, 244–247. CrossRef CAS Web of Science IUCr Journals Google Scholar
Bujak, M. & Angel, R. J. (2005). J. Solid State Chem. 178, 2237–2246. Web of Science CSD CrossRef CAS Google Scholar
Chaabouni, S., Kamoun, S., Daoud, A. & Jouini, T. (1997). J. Chem. Crystallogr. 27, 401–404. CrossRef CAS Google Scholar
Chaabouni, S., Kamoun, S. & Jaud, J. (1998). Mater. Res. Bull. 33, 377–388. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals 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
Owczarek, M., Szklarz, P., Jakubas, R. & Miniewicz, A. (2012). Dalton Trans. 41, 7285–7294. Web of Science CSD CrossRef CAS PubMed Google Scholar
Oxford Diffraction (2009). CrystAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 12| December 2013| Pages m637-m638

doi:10.1107/S1600536813028894

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

catena-Poly[N,N,N′,N′-tetra­methyl­ethylendi­ammonium [[tetra­bromido­antimonate(III)]-μ-bromido] hemihydrate]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

catena-Poly[N,N,N′,N′-tetramethylethylendiammonium [[tetrabromidoantimonate(III)]-μ-bromido] hemihydrate]