catena-Poly[heptyl­enedi­ammonium [[tetra­chloridobismuthate(III)]-μ-chlorido]]

Ouasri, A.; Rhandour, A.; Saadi, M.; El Ammari, L.

doi:10.1107/S1600536813018102

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page m437

doi:10.1107/S1600536813018102

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catena-Poly[heptylenediammonium [[tetrachloridobismuthate(III)]-μ-chlorido]]

Ali Ouasri,^a,^b ^* Ali Rhandour,^b Mohamed Saadi ^c and Lahcen El Ammari ^c

^aDépartement de Physique-Chimie, Laboratoire de Chimie, Centre Régional des Métiers de l'Education et de la Formation, Souissi Rabat, Morocco, ^bEquipe de Physico-Chimie des Matériaux Inorganiques, Université Ibn Tofail, Faculté des Sciences, BP 133, 14000 Kénitra, Morocco, and ^cLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: a_ouasri@yahoo.fr

(Received 19 June 2013; accepted 1 July 2013; online 6 July 2013)

The title organic-inorganic hybrid compound, {(C₇H₂₀N₂)[BiCl₅]}_n, consists of distorted corner-joined [BiCl₆] octahedra forming zigzag polymeric anionic chains parallel to [001], separated by columns of heptylenediammonium cations. The asymmetric unit contains two crystallographically independent bismuth metal atoms, one of which lies on an inversion centre and the other on a twofold axis. In the crystal, the polymeric chains and cations are linked by N—H⋯Cl hydrogen bonds, forming undulating layers parallel to (110).

Related literature

For potential applications of alkylammonium halogenidoantimonates and -bismuthates, see: Ciapala et al. (1997 ); Bednarska-Bolek et al. (2000 ); Bator et al. (1998 ). For the structures of related compounds see: Ouasri et al. (2001 , 2012 ); Jeghnou et al. (2005 ); Rhandour et al. (2011 ).

Experimental

Crystal data

(C₇H₂₀N₂)[BiCl₅]
M_r = 518.48
Orthorhombic, P b c n
a = 12.2451 (5) Å
b = 16.5509 (6) Å
c = 15.8934 (6) Å
V = 3221.1 (2) Å³
Z = 8
Mo Kα radiation
μ = 11.75 mm⁻¹
T = 296 K
0.36 × 0.31 × 0.27 mm

Data collection

Bruker X8 APEX Diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.512, T_max = 0.640
26890 measured reflections
3559 independent reflections
2700 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.051
S = 1.05
3559 reflections
138 parameters
H-atom parameters constrained
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.96 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H13⋯Cl2ⁱ	0.89	2.45	3.257 (4)	151
N2—H22⋯Cl4ⁱⁱ	0.89	2.37	3.222 (3)	159
Symmetry codes: (i) -x+1, -y+1, -z; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536813018102/rz5076sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813018102/rz5076Isup2.hkl

checkCIF report

Comment top

Alkylammonium halogenoantimonates and bismuthates of general formula R₂MX₅, R₃M₂X₉ and R₅M₂X₁₁ (R: organic cations, M: Sb or Bi, X: Cl, Br or I) have recently attracted considerable attention since some of these compounds have revealed interesting properties (ferroelectric and non-linear optical) which make them promising materials from the viewpoint of applications (Ciapala et al., 1997; Bednarska-Bolek et al., 2000; Bator et al., 1998). The crystal lattices of the halogenometallates compounds are built of distorted MX₆^3- octahedra which are either isolated or linked to each other by corners, edges and faces. The anionic sublattices of the halogenoantimonates and bismuthates compounds of formula R₃M₂X₉ (Ouasri et al., 2001; Jeghnou et al., 2005; Ouasri et al., 2012; Rhandour et al., 2011) are built of distorted MX₆^3- octahedra connected with each other, by corners, edges and faces, in such a way that three halogen atoms of the coordination sphere of Sb or Bi atoms are bridging and three are terminal. The aim of the present work was to study the recently synthesized title compound by X-ray diffraction to obtain informations about its crystal structure at ambient temperature.

The structure of the organic-inorganic hybrid title compound is built up from inorganic polymeric anions and organic cations (Fig. 1). In this structure, each bismuth cation is surrounded by six chlorine anions building a distorted BiCl₆^3- octahedron, with Bi—Cl distances varying from 2.5520 (8) to 2.9732 (10) Å. The octahedra are corner-joined to form one-dimensional zig-zag chains propagating along the c axis. The periodic length of this string is three octahedra. In the crystal structure, the chains and organic cations are linked together by N—H···Cl hydrogen bonds(Table 1) to build undulated sheets parallel to the (1 1 0) plane (Fig. 2).

Related literature top

For potential applications of alkylammonium halogenoantimonates and bismuthates, see: Ciapala et al. (1997); Bednarska-Bolek et al. (2000); Bator et al. (1998). For the structures of related compounds see: Ouasri et al. (2001, 2012); Jeghnou et al. (2005); Rhandour et al. (2011).

Experimental top

Single crystals of the title compound were obtained by slow evaporation, at room temperature, of an aqueous solution containing stoichiometric amounts of 1,7-diaminoheptane NH₂(CH₂)₇NH₂ (acidified with HCl in a large excess) and bismuth(III) oxide Bi₂O₃.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are represented as small circles. Symmetry codes: (a) 1-x, y, 1/2-z; (b) 1-x, 1-y, -z; (c) x, 1-y, -1/2+z.
	Fig. 2. Partial plot of the title compound, showing undulated inorganic layers linked through N–H···Cl hydrogen bonds (dashed lines).

catena-Poly[heptylenediammonium [[tetrachloridobismuthate(III)]-µ-chlorido]] top

Crystal data top

(C₇H₂₀N₂)[BiCl₅]	F(000) = 1952
M_r = 518.48	D_x = 2.138 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 3559 reflections
a = 12.2451 (5) Å	θ = 2.5–27.1°
b = 16.5509 (6) Å	µ = 11.75 mm⁻¹
c = 15.8934 (6) Å	T = 296 K
V = 3221.1 (2) Å³	Block, colourless
Z = 8	0.36 × 0.31 × 0.27 mm

Data collection top

Bruker X8 APEX Diffractometer	3559 independent reflections
Radiation source: fine-focus sealed tube	2700 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 27.1°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
T_min = 0.512, T_max = 0.640	k = −19→21
26890 measured reflections	l = −20→20

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.051	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0185P)² + 4.1437P] where P = (F_o² + 2F_c²)/3
3559 reflections	(Δ/σ)_max < 0.001
138 parameters	Δρ_max = 0.70 e Å⁻³
0 restraints	Δρ_min = −0.96 e Å⁻³

Crystal data top

(C₇H₂₀N₂)[BiCl₅]	V = 3221.1 (2) Å³
M_r = 518.48	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 12.2451 (5) Å	µ = 11.75 mm⁻¹
b = 16.5509 (6) Å	T = 296 K
c = 15.8934 (6) Å	0.36 × 0.31 × 0.27 mm

Data collection top

Bruker X8 APEX Diffractometer	3559 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2700 reflections with I > 2σ(I)
T_min = 0.512, T_max = 0.640	R_int = 0.034
26890 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	0 restraints
wR(F²) = 0.051	H-atom parameters constrained
S = 1.05	Δρ_max = 0.70 e Å⁻³
3559 reflections	Δρ_min = −0.96 e Å⁻³
138 parameters

Special details top

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
C1	0.6871 (4)	0.7642 (3)	0.0475 (3)	0.0677 (14)
H1A	0.7050	0.7509	0.1053	0.081*
H1B	0.6323	0.7259	0.0286	0.081*
C2	0.6390 (3)	0.8465 (2)	0.0455 (2)	0.0451 (9)
H2A	0.6214	0.8611	−0.0121	0.054*
H2B	0.6916	0.8853	0.0668	0.054*
C3	0.5365 (3)	0.8490 (2)	0.0987 (3)	0.0463 (9)
H3A	0.4841	0.8114	0.0750	0.056*
H3B	0.5547	0.8298	0.1547	0.056*
C4	0.4816 (3)	0.9305 (2)	0.1073 (3)	0.0441 (9)
H4A	0.4584	0.9489	0.0522	0.053*
H4B	0.5339	0.9693	0.1290	0.053*
C5	0.3835 (3)	0.9273 (2)	0.1654 (2)	0.0415 (9)
H5A	0.3273	0.8947	0.1389	0.050*
H5B	0.4048	0.9002	0.2169	0.050*
C6	0.3346 (3)	1.0084 (2)	0.1881 (2)	0.0401 (9)
H6A	0.3904	1.0421	0.2134	0.048*
H6B	0.3094	1.0350	0.1373	0.048*
C7	0.2416 (4)	0.9995 (2)	0.2478 (2)	0.0475 (11)
H7A	0.1834	0.9698	0.2204	0.057*
H7B	0.2655	0.9683	0.2960	0.057*
N1	0.7835 (4)	0.7542 (3)	−0.0032 (2)	0.0658 (11)
H11	0.8014	0.7021	−0.0052	0.079*
H12	0.8382	0.7822	0.0192	0.079*
H13	0.7704	0.7720	−0.0551	0.079*
N2	0.1985 (3)	1.0779 (2)	0.27729 (18)	0.0453 (8)
H21	0.1546	1.0699	0.3211	0.054*
H22	0.1612	1.1015	0.2359	0.054*
H23	0.2537	1.1097	0.2926	0.054*
Cl1	0.55628 (8)	0.15799 (5)	0.13916 (5)	0.0390 (2)
Cl2	0.29126 (8)	0.25115 (6)	0.19982 (6)	0.0504 (2)
Cl3	0.54355 (11)	0.38672 (7)	0.12014 (7)	0.0637 (3)
Cl4	0.54647 (9)	0.38534 (6)	−0.11631 (6)	0.0493 (2)
Cl5	0.29132 (8)	0.45097 (6)	−0.01712 (6)	0.0465 (2)
Bi1	0.5000	0.261494 (10)	0.2500	0.02717 (6)
Bi2	0.5000	0.5000	0.0000	0.02820 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.073 (3)	0.062 (3)	0.068 (3)	0.024 (3)	0.022 (3)	0.008 (2)
C2	0.047 (2)	0.043 (2)	0.045 (2)	0.0008 (18)	−0.0039 (18)	−0.0019 (17)
C3	0.052 (2)	0.040 (2)	0.046 (2)	−0.0019 (19)	0.0013 (19)	−0.0077 (18)
C4	0.052 (2)	0.035 (2)	0.046 (2)	0.0019 (17)	0.0019 (18)	−0.0005 (17)
C5	0.045 (2)	0.038 (2)	0.041 (2)	−0.0006 (17)	0.0000 (17)	0.0060 (16)
C6	0.041 (2)	0.041 (2)	0.038 (2)	−0.0072 (16)	0.0024 (18)	−0.0011 (16)
C7	0.043 (2)	0.046 (3)	0.054 (3)	0.0006 (17)	0.007 (2)	0.0091 (19)
N1	0.065 (3)	0.076 (3)	0.057 (2)	0.012 (2)	−0.002 (2)	0.0057 (19)
N2	0.0392 (17)	0.061 (2)	0.0356 (15)	−0.0007 (16)	0.0033 (14)	0.0017 (15)
Cl1	0.0461 (5)	0.0372 (5)	0.0336 (4)	−0.0012 (4)	0.0044 (4)	−0.0097 (4)
Cl2	0.0391 (5)	0.0545 (6)	0.0575 (6)	0.0042 (4)	−0.0104 (5)	0.0104 (5)
Cl3	0.0720 (7)	0.0646 (8)	0.0546 (6)	−0.0119 (6)	−0.0077 (6)	0.0313 (6)
Cl4	0.0520 (6)	0.0497 (6)	0.0463 (5)	−0.0004 (5)	0.0114 (5)	−0.0126 (5)
Cl5	0.0408 (5)	0.0531 (6)	0.0457 (5)	−0.0049 (4)	0.0064 (4)	−0.0023 (4)
Bi1	0.03136 (10)	0.02362 (10)	0.02653 (9)	0.000	0.00112 (8)	0.000
Bi2	0.03338 (10)	0.02704 (11)	0.02418 (9)	−0.00266 (8)	0.00014 (8)	0.00424 (6)

Geometric parameters (Å, º) top

C1—N1	1.439 (6)	C7—H7A	0.9700
C1—C2	1.485 (6)	C7—H7B	0.9700
C1—H1A	0.9700	N1—H11	0.8900
C1—H1B	0.9700	N1—H12	0.8900
C2—C3	1.515 (5)	N1—H13	0.8900
C2—H2A	0.9700	N2—H21	0.8900
C2—H2B	0.9700	N2—H22	0.8900
C3—C4	1.513 (6)	N2—H23	0.8900
C3—H3A	0.9700	Cl1—Bi1	2.5520 (8)
C3—H3B	0.9700	Cl2—Bi1	2.6830 (10)
C4—C5	1.517 (5)	Cl3—Bi2	2.7287 (10)
C4—H4A	0.9700	Cl3—Bi1	2.9732 (10)
C4—H4B	0.9700	Cl4—Bi2	2.7097 (9)
C5—C6	1.512 (5)	Cl5—Bi2	2.6948 (9)
C5—H5A	0.9700	Bi1—Cl1ⁱ	2.5520 (8)
C5—H5B	0.9700	Bi1—Cl2ⁱ	2.6830 (10)
C6—C7	1.490 (5)	Bi1—Cl3ⁱ	2.9732 (10)
C6—H6A	0.9700	Bi2—Cl5ⁱⁱ	2.6948 (9)
C6—H6B	0.9700	Bi2—Cl4ⁱⁱ	2.7097 (9)
C7—N2	1.477 (5)	Bi2—Cl3ⁱⁱ	2.7287 (10)

N1—C1—C2	114.8 (4)	C1—N1—H12	109.5
N1—C1—H1A	108.6	H11—N1—H12	109.5
C2—C1—H1A	108.6	C1—N1—H13	109.5
N1—C1—H1B	108.6	H11—N1—H13	109.5
C2—C1—H1B	108.6	H12—N1—H13	109.5
H1A—C1—H1B	107.6	C7—N2—H21	109.5
C1—C2—C3	109.9 (3)	C7—N2—H22	109.5
C1—C2—H2A	109.7	H21—N2—H22	109.5
C3—C2—H2A	109.7	C7—N2—H23	109.5
C1—C2—H2B	109.7	H21—N2—H23	109.5
C3—C2—H2B	109.7	H22—N2—H23	109.5
H2A—C2—H2B	108.2	Bi2—Cl3—Bi1	158.39 (5)
C4—C3—C2	116.2 (3)	Cl1—Bi1—Cl1ⁱ	95.67 (4)
C4—C3—H3A	108.2	Cl1—Bi1—Cl2ⁱ	84.55 (3)
C2—C3—H3A	108.2	Cl1ⁱ—Bi1—Cl2ⁱ	90.53 (3)
C4—C3—H3B	108.2	Cl1—Bi1—Cl2	90.53 (3)
C2—C3—H3B	108.2	Cl1ⁱ—Bi1—Cl2	84.55 (3)
H3A—C3—H3B	107.4	Cl2ⁱ—Bi1—Cl2	172.69 (4)
C3—C4—C5	112.0 (3)	Cl1—Bi1—Cl3ⁱ	174.59 (3)
C3—C4—H4A	109.2	Cl1ⁱ—Bi1—Cl3ⁱ	86.58 (3)
C5—C4—H4A	109.2	Cl2ⁱ—Bi1—Cl3ⁱ	90.52 (3)
C3—C4—H4B	109.2	Cl2—Bi1—Cl3ⁱ	94.58 (4)
C5—C4—H4B	109.2	Cl1—Bi1—Cl3	86.58 (3)
H4A—C4—H4B	107.9	Cl1ⁱ—Bi1—Cl3	174.59 (3)
C6—C5—C4	115.3 (3)	Cl2ⁱ—Bi1—Cl3	94.58 (4)
C6—C5—H5A	108.4	Cl2—Bi1—Cl3	90.52 (3)
C4—C5—H5A	108.4	Cl3ⁱ—Bi1—Cl3	91.61 (5)
C6—C5—H5B	108.4	Cl5ⁱⁱ—Bi2—Cl5	180.0
C4—C5—H5B	108.4	Cl5ⁱⁱ—Bi2—Cl4ⁱⁱ	85.37 (3)
H5A—C5—H5B	107.5	Cl5—Bi2—Cl4ⁱⁱ	94.63 (3)
C7—C6—C5	111.6 (3)	Cl5ⁱⁱ—Bi2—Cl4	94.63 (3)
C7—C6—H6A	109.3	Cl5—Bi2—Cl4	85.37 (3)
C5—C6—H6A	109.3	Cl4ⁱⁱ—Bi2—Cl4	180.00 (4)
C7—C6—H6B	109.3	Cl5ⁱⁱ—Bi2—Cl3ⁱⁱ	92.81 (3)
C5—C6—H6B	109.3	Cl5—Bi2—Cl3ⁱⁱ	87.19 (3)
H6A—C6—H6B	108.0	Cl4ⁱⁱ—Bi2—Cl3ⁱⁱ	87.43 (3)
N2—C7—C6	112.9 (3)	Cl4—Bi2—Cl3ⁱⁱ	92.57 (3)
N2—C7—H7A	109.0	Cl5ⁱⁱ—Bi2—Cl3	87.19 (3)
C6—C7—H7A	109.0	Cl5—Bi2—Cl3	92.81 (3)
N2—C7—H7B	109.0	Cl4ⁱⁱ—Bi2—Cl3	92.57 (3)
C6—C7—H7B	109.0	Cl4—Bi2—Cl3	87.43 (3)
H7A—C7—H7B	107.8	Cl3ⁱⁱ—Bi2—Cl3	180.00 (4)
C1—N1—H11	109.5

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H13···Cl2ⁱⁱ	0.89	2.45	3.257 (4)	151
N2—H22···Cl4ⁱⁱⁱ	0.89	2.37	3.222 (3)	159

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

Experimental details

Crystal data
Chemical formula	(C₇H₂₀N₂)[BiCl₅]
M_r	518.48
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	296
a, b, c (Å)	12.2451 (5), 16.5509 (6), 15.8934 (6)
V (Å³)	3221.1 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	11.75
Crystal size (mm)	0.36 × 0.31 × 0.27

Data collection
Diffractometer	Bruker X8 APEX Diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.512, 0.640
No. of measured, independent and observed [I > 2σ(I)] reflections	26890, 3559, 2700
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.051, 1.05
No. of reflections	3559
No. of parameters	138
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.96

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H13···Cl2ⁱ	0.89	2.45	3.257 (4)	150.8
N2—H22···Cl4ⁱⁱ	0.89	2.37	3.222 (3)	159.3

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

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

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