Bis(1-methyl­piperazine-1,4-diium) di-μ-bromido-bis­[tetra­bromido­bismuthate(III)] dihydrate

Essid, M.; Roisnel, T.; Marouani, H.

doi:10.1107/S1600536814009805

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Pages m202-m203

doi:10.1107/S1600536814009805

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Bis(1-methylpiperazine-1,4-diium) di-μ-bromido-bis[tetrabromidobismuthate(III)] dihydrate

Manel Essid,^a ^* Thierry Roisnel ^b and Houda Marouani ^a

^aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia, and ^bCentre de Diffractométrie X, UMR 6226 CNRS, Unité Sciences Chimiques de Rennes, Université de Rennes I, 263 Avenue du Général Leclerc, 35042 Rennes, France
^*Correspondence e-mail: essidmanel@voila.fr

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 29 April 2014; accepted 30 April 2014; online 10 May 2014)

In the title hydrated salt, (C₅H₁₄N₂)₂[Bi₂Br₁₀]·2H₂O, the complete [Bi₂Br₁₀]⁴⁻ bioctahedron is generated by crystallographic inversion symmetry. The diprotonated piperazine ring adopts a chair conformation, with the methyl group occupying an equatorial position. In the crystal, the tetraanions and water molecules are linked by O—H⋯Br and O—H⋯(Br,Br) hydrogen bonds to generate [100] chains. The chains are crosslinked by N—H⋯Br, N—H⋯O and C—H⋯Br hydrogen bonds originating from the piperazinediium dications, thereby forming a three-dimensional network.

CCDC reference: 1000442

Related literature

For another decabromidodibismuthate(III) compound, see: Li et al. (2006 ). For related methylpiperazin-1,4-diium salts, see: Dutkiewicz et al. (2011 ); Essid et al. (2014 ). For related piperazine derivatives, see: Marouani et al. (2010 ); Essid et al. (2010 ).

Experimental

Crystal data

(C₅H₁₄N₂)₂[Bi₂Br₁₀]·2H₂O
M_r = 1457.46
Monoclinic, P 2₁ /c
a = 7.9263 (3) Å
b = 19.0424 (7) Å
c = 12.5861 (4) Å
β = 125.770 (2)°
V = 1541.35 (9) Å³
Z = 2
Mo Kα radiation
μ = 24.38 mm⁻¹
T = 150 K
0.15 × 0.12 × 0.07 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ) T_min = 0.071, T_max = 0.182
23912 measured reflections
3525 independent reflections
3262 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.056
S = 1.09
3525 reflections
136 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.23 e Å⁻³
Δρ_min = −1.52 e Å⁻³

Table 1
Selected bond lengths (Å)

Bi—Br3	2.7441 (5)
Bi—Br4	2.7714 (5)
Bi—Br5	2.7730 (5)
Bi—Br2	2.8784 (5)
Bi—Br1	2.9746 (5)
Bi—Br1ⁱ	3.0056 (5)
Symmetry code: (i) -x, -y-1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Br5	0.91	2.66	3.396 (4)	138
N1—H1⋯Br2	0.91	2.85	3.486 (4)	128
N2—H2C⋯O	0.90	1.91	2.793 (6)	167
N2—H2D⋯Br2ⁱⁱ	0.90	2.60	3.371 (4)	143
O—H2⋯Br5ⁱⁱⁱ	0.94 (1)	2.91 (7)	3.522 (4)	123 (6)
O—H2⋯Br1ⁱⁱⁱ	0.94 (1)	2.84 (7)	3.531 (4)	131 (7)
O—H3⋯Br3^iv	0.95 (1)	2.59 (2)	3.501 (4)	162 (6)
C2—H2B⋯Br2^v	0.97	2.80	3.649 (5)	147
Symmetry codes: (ii) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) $[x+1, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and CRYSCAL (T. Roisnel, local program).

Supporting information

CCDC reference: 1000442

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814009805/hb7225sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814009805/hb7225Isup2.hkl

checkCIF report

Comment top

As a part of our study of crystal packing containing piperazine derivatives (Marouani et al., 2010; Essid et al., 2010; Essid et al., 2014), we report here the preparation and the structural investigation of a new compound, (C₅H₁₄N₂)₂Bi₂Br₁₀·2H₂O, (I)

The crystal structure of the title compound (I) is built up of two 1-methylpiperazinium dications, two water molecules and decabromodibismuthate tetraanions; the latter have two octahedra sharing a common edge and occupy special positions with a centre of symmetry at the centre of the Bi₂Br₂ ring. Its geometrical configuration is depicted in figure 1. The half of this formula constitutes the asymmetric unit in the atomic arrangement. In the title compound (I) the [Bi₂Br₁₀]^4- bioctahedra anions are connected through O–H···Br hydrogen bonds (via water molecules) and form infinite unidimensional chains of composition [Bi₂Br₁₀(H₂O)₂]_n^4n- parallel to the a axis (Fig.2). These chains are themselves interconnected by means of N–H···Br, N–H···O and C–H···Br bonds originating from the [C₅H₁₄N₂]²⁺ entities, forming a three-dimensional network (Fig. 3). The coordination octahedral of the bismuth atoms are formed by six bromine atoms, as shown in Fig. 1. The Bi–Br distances listed in Table 1 vary from 2.7441 (5) to 3.0056 (5) Å with mean value of 2.8579 Å. The Br–Bi–Br angles range from 85.170 (15)° to 99.774 (14)° and from 170.436 (15)° to 173.695 (15)°, indicating that the BiBr₆ octahedron is distorted. These values are in agreement with those commonly observed in other organic decabromodibismuthate(III) compound (Li et al., 2006). Geometrical parameters of the methylpiperazin-1,4-dium dications are found to be in agreement with those reported in related methylpiperazin-1,4-diium salts (Dutkiewicz et al., 2011; Essid et al., 2014). The cyclic amine adopts a chair conformation with the methyl group occupying an equatorial position, with puckering parameters: Q = 0.573 (5) Å, θ = 0.8 (5)° and ϕ = 116 (4)° and atoms N1 and N2 deviating by -0.314 and 0.322 Å from the least-squares plane defined by the remaining atoms in the ring. The cations are linked onto the anionic chains, by forming H-bonds with the bromine and oxygen atoms with donor-acceptor distances in the range 2.793 (6)–3.649 (5) Å (Table 2).

Related literature top

For another decabromidodibismuthate(III) compound, see: Li et al. (2006). For related methylpiperazin-1,4-diium salts, see: Dutkiewicz et al. (2011); Essid et al. (2010, 2014). For a related piperazine derivative, see: Marouani et al. (2010). [Revised Rel. lit. OK?]

Experimental top

Bismuth(III) nitrate and 1-(methyl) piperazine were dissolved in a concentrated HBr solution in the presence of ethanol (40 ml) and water (20 ml) in a stoichiometric ratio. Colourless prisms of the title compound were obtained by slow evaporation of this solution at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 (Bruker, 2006); data reduction: APEX2 (Bruker, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 2012) and CRYSCAL (T. Roisnel, local program).

Figures top

	Fig. 1. An ORTEP view of (I) with displacement ellipsoids drawn at the 50% probability level. Symmetry code: i: -x, -y, -z.
	Fig. 2. Projection of the corrugated inorganic chains along the c axis.
	Fig. 3. Projection of (I) along the a axis. The H-atoms not involved in H-bonding are omitted.

Bis(1-methylpiperazine-1,4-diium) di-µ-bromido-bis[tetrabromidobismuthate(III)] dihydrate top

Crystal data top

(C₅H₁₄N₂)₂[Bi₂Br₁₀]·2H₂O	F(000) = 1304
M_r = 1457.46	D_x = 3.140 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9944 reflections
a = 7.9263 (3) Å	θ = 2.8–27.5°
b = 19.0424 (7) Å	µ = 24.38 mm⁻¹
c = 12.5861 (4) Å	T = 150 K
β = 125.770 (2)°	Prism, colourless
V = 1541.35 (9) Å³	0.15 × 0.12 × 0.07 mm
Z = 2

Data collection top

Bruker APEXII diffractometer	3262 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
CCD rotation images, thin slices scans	θ_max = 27.5°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −10→10
T_min = 0.071, T_max = 0.182	k = −22→24
23912 measured reflections	l = −13→12
3525 independent 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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.056	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0151P)² + 6.909P] where P = (F_o² + 2F_c²)/3
3525 reflections	(Δ/σ)_max = 0.041
136 parameters	Δρ_max = 1.23 e Å⁻³
3 restraints	Δρ_min = −1.52 e Å⁻³

Crystal data top

(C₅H₁₄N₂)₂[Bi₂Br₁₀]·2H₂O	V = 1541.35 (9) Å³
M_r = 1457.46	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.9263 (3) Å	µ = 24.38 mm⁻¹
b = 19.0424 (7) Å	T = 150 K
c = 12.5861 (4) Å	0.15 × 0.12 × 0.07 mm
β = 125.770 (2)°

Data collection top

Bruker APEXII diffractometer	3525 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	3262 reflections with I > 2σ(I)
T_min = 0.071, T_max = 0.182	R_int = 0.051
23912 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	3 restraints
wR(F²) = 0.056	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 1.23 e Å⁻³
3525 reflections	Δρ_min = −1.52 e Å⁻³
136 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
Bi	0.10118 (2)	−0.407806 (8)	0.622821 (15)	0.01138 (6)
Br1	0.27752 (7)	−0.49972 (2)	0.51922 (4)	0.01697 (10)
Br2	−0.00499 (8)	−0.31232 (3)	0.41496 (5)	0.02036 (11)
Br3	−0.12297 (8)	−0.32553 (3)	0.67787 (5)	0.02123 (11)
Br4	0.25521 (8)	−0.49702 (3)	0.83467 (5)	0.02381 (12)
Br5	0.46641 (7)	−0.33162 (2)	0.77789 (5)	0.02014 (11)
O	0.2175 (6)	0.02902 (19)	0.6937 (4)	0.0248 (8)
N1	0.3077 (6)	−0.1749 (2)	0.6194 (4)	0.0145 (8)
H1	0.2760	−0.2201	0.6249	0.017*
C1	0.4166 (8)	−0.1760 (3)	0.5543 (5)	0.0235 (11)
H1A	0.3234	−0.1933	0.4665	0.035*
H1B	0.5361	−0.2061	0.6025	0.035*
H1C	0.4600	−0.1292	0.5522	0.035*
C2	0.4472 (7)	−0.1466 (3)	0.7560 (4)	0.0167 (9)
H2A	0.4885	−0.0990	0.7534	0.020*
H2B	0.5718	−0.1751	0.8064	0.020*
C3	0.3371 (8)	−0.1467 (3)	0.8219 (5)	0.0195 (10)
H3A	0.3068	−0.1946	0.8317	0.023*
H3B	0.4269	−0.1261	0.9085	0.023*
N2	0.1400 (6)	−0.1059 (2)	0.7427 (4)	0.0168 (8)
H2C	0.1693	−0.0607	0.7387	0.020*
H2D	0.0746	−0.1073	0.7818	0.020*
C4	0.0000 (7)	−0.1347 (3)	0.6073 (5)	0.0184 (10)
H4A	−0.1254	−0.1065	0.5570	0.022*
H4B	−0.0397	−0.1824	0.6109	0.022*
C5	0.1080 (7)	−0.1344 (2)	0.5413 (5)	0.0177 (10)
H5A	0.0174	−0.1550	0.4548	0.021*
H5B	0.1368	−0.0863	0.5310	0.021*
H2	0.360 (4)	0.035 (4)	0.730 (7)	0.08 (3)*
H3	0.203 (10)	0.062 (3)	0.745 (6)	0.05 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Bi	0.00972 (9)	0.01144 (9)	0.01281 (9)	−0.00006 (6)	0.00649 (7)	−0.00024 (6)
Br1	0.0124 (2)	0.0197 (2)	0.0184 (2)	0.00040 (17)	0.0087 (2)	−0.00129 (17)
Br2	0.0198 (3)	0.0218 (2)	0.0206 (2)	0.00041 (19)	0.0125 (2)	0.00260 (18)
Br3	0.0254 (3)	0.0199 (2)	0.0242 (2)	0.00474 (19)	0.0178 (2)	−0.00034 (18)
Br4	0.0202 (3)	0.0235 (3)	0.0190 (2)	−0.00190 (19)	0.0065 (2)	0.00602 (19)
Br5	0.0143 (2)	0.0189 (2)	0.0224 (2)	−0.00246 (18)	0.0080 (2)	−0.00086 (18)
O	0.0156 (18)	0.0231 (19)	0.028 (2)	−0.0021 (15)	0.0085 (16)	0.0002 (15)
N1	0.016 (2)	0.0114 (18)	0.018 (2)	−0.0006 (15)	0.0112 (17)	−0.0011 (15)
C1	0.026 (3)	0.026 (3)	0.029 (3)	−0.001 (2)	0.022 (2)	0.000 (2)
C2	0.010 (2)	0.021 (2)	0.015 (2)	−0.0014 (18)	0.0052 (19)	−0.0039 (18)
C3	0.019 (2)	0.024 (3)	0.016 (2)	0.001 (2)	0.010 (2)	0.0007 (19)
N2	0.018 (2)	0.017 (2)	0.018 (2)	0.0023 (16)	0.0122 (18)	−0.0001 (16)
C4	0.013 (2)	0.021 (2)	0.019 (2)	0.0005 (19)	0.008 (2)	−0.0023 (19)
C5	0.016 (2)	0.016 (2)	0.013 (2)	0.0031 (18)	0.0036 (19)	0.0008 (17)

Geometric parameters (Å, º) top

Bi—Br3	2.7441 (5)	C1—H1C	0.9600
Bi—Br4	2.7714 (5)	C2—C3	1.515 (7)
Bi—Br5	2.7730 (5)	C2—H2A	0.9700
Bi—Br2	2.8784 (5)	C2—H2B	0.9700
Bi—Br1	2.9746 (5)	C3—N2	1.489 (6)
Bi—Br1ⁱ	3.0056 (5)	C3—H3A	0.9700
Br1—Biⁱ	3.0056 (5)	C3—H3B	0.9700
O—H2	0.943 (10)	N2—C4	1.492 (6)
O—H3	0.945 (10)	N2—H2C	0.9000
N1—C1	1.497 (6)	N2—H2D	0.9000
N1—C2	1.500 (6)	C4—C5	1.501 (7)
N1—C5	1.500 (6)	C4—H4A	0.9700
N1—H1	0.9100	C4—H4B	0.9700
C1—H1A	0.9600	C5—H5A	0.9700
C1—H1B	0.9600	C5—H5B	0.9700

Br3—Bi—Br4	95.349 (16)	N1—C2—H2A	109.5
Br3—Bi—Br5	95.001 (16)	C3—C2—H2A	109.5
Br4—Bi—Br5	87.249 (15)	N1—C2—H2B	109.5
Br3—Bi—Br2	88.872 (15)	C3—C2—H2B	109.5
Br4—Bi—Br2	172.766 (16)	H2A—C2—H2B	108.1
Br5—Bi—Br2	86.531 (15)	N2—C3—C2	110.3 (4)
Br3—Bi—Br1	170.436 (15)	N2—C3—H3A	109.6
Br4—Bi—Br1	90.312 (15)	C2—C3—H3A	109.6
Br5—Bi—Br1	92.961 (15)	N2—C3—H3B	109.6
Br2—Bi—Br1	86.326 (14)	C2—C3—H3B	109.6
Br3—Bi—Br1ⁱ	85.170 (15)	H3A—C3—H3B	108.1
Br4—Bi—Br1ⁱ	86.460 (14)	C3—N2—C4	111.2 (4)
Br5—Bi—Br1ⁱ	173.695 (15)	C3—N2—H2C	109.4
Br2—Bi—Br1ⁱ	99.774 (14)	C4—N2—H2C	109.4
Br1—Bi—Br1ⁱ	87.498 (13)	C3—N2—H2D	109.4
Bi—Br1—Biⁱ	92.502 (13)	C4—N2—H2D	109.4
H2—O—H3	100 (2)	H2C—N2—H2D	108.0
C1—N1—C2	111.0 (4)	N2—C4—C5	110.3 (4)
C1—N1—C5	111.9 (4)	N2—C4—H4A	109.6
C2—N1—C5	110.8 (3)	C5—C4—H4A	109.6
C1—N1—H1	107.7	N2—C4—H4B	109.6
C2—N1—H1	107.7	C5—C4—H4B	109.6
C5—N1—H1	107.7	H4A—C4—H4B	108.1
N1—C1—H1A	109.5	N1—C5—C4	111.1 (4)
N1—C1—H1B	109.5	N1—C5—H5A	109.4
H1A—C1—H1B	109.5	C4—C5—H5A	109.4
N1—C1—H1C	109.5	N1—C5—H5B	109.4
H1A—C1—H1C	109.5	C4—C5—H5B	109.4
H1B—C1—H1C	109.5	H5A—C5—H5B	108.0
N1—C2—C3	110.7 (4)

Symmetry code: (i) −x, −y−1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Br5	0.91	2.66	3.396 (4)	138
N1—H1···Br2	0.91	2.85	3.486 (4)	128
N2—H2C···O	0.90	1.91	2.793 (6)	167
N2—H2D···Br2ⁱⁱ	0.90	2.60	3.371 (4)	143
O—H2···Br5ⁱⁱⁱ	0.94 (1)	2.91 (7)	3.522 (4)	123 (6)
O—H2···Br1ⁱⁱⁱ	0.94 (1)	2.84 (7)	3.531 (4)	131 (7)
O—H3···Br3^iv	0.95 (1)	2.59 (2)	3.501 (4)	162 (6)
C2—H2B···Br2^v	0.97	2.80	3.649 (5)	147

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

Selected geometric parameters (Å, º) top

Bi—Br3	2.7441 (5)	Bi—Br2	2.8784 (5)
Bi—Br4	2.7714 (5)	Bi—Br1	2.9746 (5)
Bi—Br5	2.7730 (5)	Bi—Br1ⁱ	3.0056 (5)

Bi—Br1—Biⁱ	92.502 (13)

Symmetry code: (i) −x, −y−1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Br5	0.91	2.66	3.396 (4)	138
N1—H1···Br2	0.91	2.85	3.486 (4)	128
N2—H2C···O	0.90	1.91	2.793 (6)	167
N2—H2D···Br2ⁱⁱ	0.90	2.60	3.371 (4)	143
O—H2···Br5ⁱⁱⁱ	0.943 (10)	2.91 (7)	3.522 (4)	123 (6)
O—H2···Br1ⁱⁱⁱ	0.943 (10)	2.84 (7)	3.531 (4)	131 (7)
O—H3···Br3^iv	0.945 (10)	2.59 (2)	3.501 (4)	162 (6)
C2—H2B···Br2^v	0.97	2.80	3.649 (5)	147

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

References

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Volume 70| Part 6| June 2014| Pages m202-m203

doi:10.1107/S1600536814009805

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

Bis(1-methyl­piperazine-1,4-diium) di-μ-bromido-bis­­[tetra­bromido­bis­muthate(III)] dihydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

metal-organic compounds

Bis(1-methylpiperazine-1,4-diium) di-μ-bromido-bis[tetrabromidobismuthate(III)] dihydrate