[N,N′-Bis(2,6-dichloro­benzyl­idene)propane-1,3-diamine-κ2N,N′]dibromidozinc

Khalaji, A.D.; Grivani, G.; Seyyedi, M.; Fejfarová, K.; Dušek, M.

doi:10.1107/S1600536812027997

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page m971

https://doi.org/10.1107/S1600536812027997

Open

access

[N,N′-Bis(2,6-dichlorobenzylidene)propane-1,3-diamine-κ²N,N′]dibromidozinc

Aliakbar Dehno Khalaji,^a Gholamhossein Grivani,^b Mohammad Seyyedi,^b Karla Fejfarová ^c ^* and Michal Dušek ^c

^aDepartment of Chemistry, Faculty of Science, Golestan University, Gorgan, Iran, ^bSchool of Chemistry, Damghan University, Damghan 36715-364, Iran, and ^cInstitute of Physics ASCR, v.v.i., Na Slovance 2, 182 21 Praha 8, Czech Republic
^*Correspondence e-mail: fejfarov@fzu.cz

(Received 19 June 2012; accepted 20 June 2012; online 23 June 2012)

In the title compound, [ZnBr₂(C₁₇H₁₄Cl₄N₂)], the Zn^II ion is bonded to two bromide ions and two N atoms of the diimine ligand and displays a moderately distorted tetrahedral coordination geometry. The Schiff base ligand acts as a chelating ligand and coordinates to the Zn^II atom via two N atoms.

Related literature

For related structures, see: Khalaj et al. (2008 , 2009 ); Salehzadeh et al. (2011 ); Khalaji et al. (2010 , 2011 , 2012 ). For properties and application of complexes of symmetric bidentate Schiff base ligands, see: Komatsu et al. (2007 ); Montazerozohori et al. (2011 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

[ZnBr₂(C₁₇H₁₄Cl₄N₂)]
M_r = 613.3
Monoclinic, P 2₁ /c
a = 17.0433 (3) Å
b = 9.3216 (2) Å
c = 13.6038 (2) Å
β = 97.313 (2)°
V = 2143.67 (7) Å³
Z = 4
Mo Kα radiation
μ = 5.38 mm⁻¹
T = 120 K
0.33 × 0.28 × 0.10 mm

Data collection

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.5, T_max = 1
32456 measured reflections
5469 independent reflections
4344 reflections with I > 3σ(I)
R_int = 0.032

Refinement

R[F² > 3σ(F²)] = 0.023
wR(F²) = 0.053
S = 1.32
5469 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—Br1	2.3599 (3)
Zn1—Br2	2.3371 (3)
Zn1—N1	2.0662 (16)
Zn1—N2	2.0628 (16)

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: JANA2006.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812027997/bt5947sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812027997/bt5947Isup2.hkl

checkCIF report

Comment top

Complexes of symmetric bidentate Schiff base ligands with transition metals have attracted much attention because of their catalytic (Komatsu et al., 2007) and thermal properties (Montazerozohori et al., 2011). There is substantial interest in the coordination chemistry of the zinc(II) ion (Khalaj et al., 2008, 2009; Salehzadeh et al.,2011; Khalaji et al.,2010, 2011, 2012).

The molecular structure of 1 with the atom-numbering scheme is presented in Fig. 1, and the bond lengths and angles are generally normal (Allen et al., 1987). The zinc(II) ion is coordinated by the bidentate Schiff-base ligand and two Br ions. Although a tetrahedral geometry might be expected for a four coordinated zinc(II) centre, the geometry around the zinc(II) ion is distorted by the bite angle N1—Zn1—N2 [90.24 (6)°] of the chelating ligand. On the contrary the Br1—Zn11—Br2 angle has opened up to 120.866 (11)°. The N—Zn—Br angles are also distorted from the tetrahedral values.

Related literature top

For related structures, see: Khalaj et al. (2008, 2009); Salehzadeh et al. (2011); Khalaji et al. (2010, 2011, 2012). For properties and application of complexes of symmetric bidentate Schiff base ligands, see: Komatsu et al. (2007); Montazerozohori et al. (2011). For bond-length data, see: Allen et al. (1987).

Experimental top

To a stirring solution of the (2,6-Cl-ba)₂en ligand (1 mmol, in 5 ml of chloroform) was added ZnBr₂ (1 mmol) in 10 ml of methanol and the mixture was stirred for 10 min in air at room temperature and was then left at 273 K for several days without disturbance yielding suitable crystals that subsequently were filtered off and washed with Et₂O.

Structure description top

For related structures, see: Khalaj et al. (2008, 2009); Salehzadeh et al. (2011); Khalaji et al. (2010, 2011, 2012). For properties and application of complexes of symmetric bidentate Schiff base ligands, see: Komatsu et al. (2007); Montazerozohori et al. (2011). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: JANA2006 (Petříček et al., 2006); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: JANA2006 (Petříček et al., 2006).

Figures top

Fig. 1. The molecular structure of 1. Displacement ellipsoids are drawn at the 50% probability level.

[N,N'-Bis(2,6-dichlorobenzylidene)propane-1,3- diamine-κ²N,N']dibromidozinc top

Crystal data top

[ZnBr₂(C₁₇H₁₄Cl₄N₂)]	F(000) = 1192
M_r = 613.3	D_x = 1.900 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 14022 reflections
a = 17.0433 (3) Å	θ = 3.0–29.3°
b = 9.3216 (2) Å	µ = 5.38 mm⁻¹
c = 13.6038 (2) Å	T = 120 K
β = 97.313 (2)°	Block, colourless
V = 2143.67 (7) Å³	0.33 × 0.28 × 0.10 mm
Z = 4

Data collection top

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	5469 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4344 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.032
Detector resolution: 10.3784 pixels mm^-1	θ_max = 29.4°, θ_min = 3.0°
Rotation method data acquisition using ω scans	h = −21→23
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −12→12
T_min = 0.5, T_max = 1	l = −18→17
32456 measured reflections

Refinement top

Refinement on F²	56 constraints
R[F > 3σ(F)] = 0.023	H-atom parameters constrained
wR(F) = 0.053	Weighting scheme based on measured s.u.'s w = 1/(σ²(I) + 0.0004I²)
S = 1.32	(Δ/σ)_max = 0.002
5469 reflections	Δρ_max = 0.55 e Å⁻³
235 parameters	Δρ_min = −0.43 e Å⁻³
0 restraints

Crystal data top

[ZnBr₂(C₁₇H₁₄Cl₄N₂)]	V = 2143.67 (7) Å³
M_r = 613.3	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.0433 (3) Å	µ = 5.38 mm⁻¹
b = 9.3216 (2) Å	T = 120 K
c = 13.6038 (2) Å	0.33 × 0.28 × 0.10 mm
β = 97.313 (2)°

Data collection top

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	5469 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	4344 reflections with I > 3σ(I)
T_min = 0.5, T_max = 1	R_int = 0.032
32456 measured reflections

Refinement top

R[F > 3σ(F)] = 0.023	0 restraints
wR(F) = 0.053	H-atom parameters constrained
S = 1.32	Δρ_max = 0.55 e Å⁻³
5469 reflections	Δρ_min = −0.43 e Å⁻³
235 parameters

Special details top

Experimental. Absorption correction: CrysAlisPro (Agilent Technologies, 2011) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F² for refinement carried out on F and F², respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.

The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

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

	x	y	z	U_iso*/U_eq
Zn1	0.778715 (13)	−0.01264 (2)	0.739863 (16)	0.01974 (7)
Br1	0.815993 (14)	−0.06312 (2)	0.909367 (15)	0.03043 (7)
Br2	0.768458 (12)	0.22386 (2)	0.682623 (15)	0.02510 (7)
Cl1	0.57897 (3)	−0.18717 (6)	0.46139 (4)	0.03164 (17)
Cl2	0.49527 (3)	−0.02131 (6)	0.81149 (4)	0.03069 (16)
Cl3	0.78647 (4)	−0.01110 (6)	0.42235 (4)	0.03640 (18)
Cl4	1.01713 (4)	−0.02162 (7)	0.73027 (4)	0.0435 (2)
N1	0.67043 (10)	−0.11134 (16)	0.70285 (12)	0.0204 (5)
N2	0.83223 (9)	−0.16701 (17)	0.66248 (11)	0.0190 (5)
C1	0.72353 (12)	−0.3466 (2)	0.66028 (16)	0.0272 (6)
C2	0.67041 (12)	−0.2659 (2)	0.72376 (16)	0.0273 (6)
C3	0.60879 (12)	−0.0487 (2)	0.66383 (14)	0.0216 (6)
C4	0.52967 (11)	−0.1151 (2)	0.63559 (15)	0.0219 (6)
C5	0.50947 (12)	−0.1818 (2)	0.54428 (15)	0.0252 (6)
C6	0.43508 (13)	−0.2408 (2)	0.51740 (17)	0.0321 (7)
C7	0.37960 (13)	−0.2328 (2)	0.58284 (17)	0.0342 (7)
C8	0.39751 (12)	−0.1666 (2)	0.67387 (17)	0.0306 (7)
C9	0.47174 (12)	−0.1085 (2)	0.69829 (15)	0.0240 (6)
C10	0.81108 (12)	−0.3168 (2)	0.68397 (14)	0.0218 (6)
C11	0.87837 (12)	−0.1473 (2)	0.59844 (14)	0.0232 (6)
C12	0.90508 (12)	−0.0029 (2)	0.57246 (14)	0.0223 (6)
C13	0.86796 (12)	0.0692 (2)	0.48978 (15)	0.0248 (6)
C14	0.89235 (13)	0.2026 (2)	0.46228 (17)	0.0308 (7)
C15	0.95599 (13)	0.2659 (2)	0.51856 (16)	0.0312 (7)
C16	0.99483 (13)	0.1988 (2)	0.60108 (16)	0.0300 (7)
C17	0.96911 (12)	0.0647 (2)	0.62674 (15)	0.0260 (6)
H1a	0.714222	−0.447812	0.664797	0.0326*
H1b	0.706896	−0.326754	0.591541	0.0326*
H2a	0.617401	−0.302232	0.710663	0.0327*
H2b	0.688664	−0.281934	0.792584	0.0327*
H3	0.613239	0.052004	0.650974	0.0259*
H6	0.422365	−0.286607	0.45416	0.0386*
H7	0.328059	−0.273674	0.564947	0.0411*
H8	0.358864	−0.161171	0.719285	0.0367*
H10a	0.827835	−0.337727	0.752531	0.0262*
H10b	0.840072	−0.381379	0.64704	0.0262*
H11	0.896906	−0.229113	0.56525	0.0278*
H14	0.865572	0.250488	0.405122	0.037*
H15	0.973645	0.35864	0.499922	0.0375*
H16	1.038872	0.244152	0.639989	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.01828 (12)	0.01772 (12)	0.02378 (12)	−0.00064 (9)	0.00483 (9)	−0.00078 (9)
Br1	0.04287 (14)	0.02484 (11)	0.02295 (11)	−0.00147 (9)	0.00178 (9)	0.00022 (8)
Br2	0.02661 (12)	0.01722 (10)	0.03323 (12)	0.00196 (8)	0.01065 (9)	0.00062 (8)
Cl1	0.0296 (3)	0.0355 (3)	0.0303 (3)	0.0012 (2)	0.0057 (2)	−0.0026 (2)
Cl2	0.0303 (3)	0.0317 (3)	0.0313 (3)	0.0085 (2)	0.0086 (2)	0.0035 (2)
Cl3	0.0359 (3)	0.0301 (3)	0.0389 (3)	0.0017 (2)	−0.0119 (3)	−0.0036 (2)
Cl4	0.0394 (4)	0.0537 (4)	0.0335 (3)	−0.0191 (3)	−0.0102 (3)	0.0086 (3)
N1	0.0173 (8)	0.0191 (8)	0.0252 (8)	0.0008 (7)	0.0047 (7)	0.0012 (7)
N2	0.0159 (8)	0.0209 (8)	0.0194 (8)	0.0000 (7)	−0.0008 (7)	−0.0022 (7)
C1	0.0230 (11)	0.0162 (10)	0.0405 (12)	−0.0015 (8)	−0.0033 (9)	0.0002 (9)
C2	0.0165 (10)	0.0208 (10)	0.0439 (13)	−0.0020 (8)	0.0016 (9)	0.0114 (9)
C3	0.0220 (11)	0.0187 (10)	0.0251 (10)	0.0001 (8)	0.0067 (9)	−0.0002 (8)
C4	0.0161 (10)	0.0181 (10)	0.0312 (10)	0.0046 (8)	0.0019 (8)	0.0056 (8)
C5	0.0222 (11)	0.0218 (10)	0.0315 (11)	0.0032 (8)	0.0038 (9)	0.0042 (9)
C6	0.0275 (12)	0.0282 (11)	0.0387 (13)	−0.0011 (9)	−0.0034 (10)	0.0014 (10)
C7	0.0188 (11)	0.0308 (12)	0.0508 (15)	−0.0022 (9)	−0.0042 (10)	0.0084 (11)
C8	0.0193 (11)	0.0291 (11)	0.0444 (13)	0.0042 (9)	0.0078 (10)	0.0108 (10)
C9	0.0224 (11)	0.0212 (10)	0.0283 (10)	0.0059 (8)	0.0029 (9)	0.0060 (9)
C10	0.0210 (10)	0.0171 (9)	0.0270 (10)	0.0031 (8)	0.0015 (8)	0.0025 (8)
C11	0.0194 (10)	0.0253 (10)	0.0243 (10)	0.0003 (8)	0.0006 (8)	−0.0043 (9)
C12	0.0207 (10)	0.0235 (10)	0.0238 (10)	0.0017 (8)	0.0075 (8)	−0.0045 (8)
C13	0.0222 (11)	0.0244 (10)	0.0275 (10)	0.0028 (8)	0.0026 (9)	−0.0071 (9)
C14	0.0345 (13)	0.0234 (11)	0.0352 (12)	0.0092 (9)	0.0067 (10)	0.0022 (9)
C15	0.0307 (12)	0.0211 (10)	0.0444 (13)	−0.0022 (9)	0.0147 (11)	−0.0012 (10)
C16	0.0254 (12)	0.0305 (12)	0.0355 (12)	−0.0097 (9)	0.0090 (10)	−0.0074 (10)
C17	0.0230 (11)	0.0325 (11)	0.0228 (10)	−0.0038 (9)	0.0042 (9)	−0.0024 (9)

Geometric parameters (Å, º) top

Zn1—Br1	2.3599 (3)	C6—C7	1.381 (3)
Zn1—Br2	2.3371 (3)	C6—H6	0.96
Zn1—N1	2.0662 (16)	C7—C8	1.383 (3)
Zn1—N2	2.0628 (16)	C7—H7	0.96
N1—C2	1.469 (2)	C8—C9	1.377 (3)
N1—C3	1.259 (2)	C8—H8	0.96
N2—C10	1.481 (2)	C10—H10a	0.96
N2—C11	1.259 (3)	C10—H10b	0.96
C1—C2	1.526 (3)	C11—C12	1.478 (3)
C1—C10	1.512 (3)	C11—H11	0.96
C1—H1a	0.96	C12—C13	1.391 (3)
C1—H1b	0.96	C12—C17	1.388 (3)
C2—H2a	0.96	C13—C14	1.379 (3)
C2—H2b	0.96	C14—C15	1.378 (3)
C3—C4	1.489 (3)	C14—H14	0.96
C3—H3	0.96	C15—C16	1.379 (3)
C4—C5	1.393 (3)	C15—H15	0.96
C4—C9	1.386 (3)	C16—C17	1.384 (3)
C5—C6	1.388 (3)	C16—H16	0.96

Br1—Zn1—Br2	120.866 (11)	C5—C6—H6	120.45
Br1—Zn1—N1	105.69 (5)	C7—C6—H6	120.45
Br1—Zn1—N2	106.14 (4)	C6—C7—C8	120.7 (2)
Br2—Zn1—N1	108.19 (4)	C6—C7—H7	119.65
Br2—Zn1—N2	120.47 (4)	C8—C7—H7	119.65
N1—Zn1—N2	90.24 (6)	C7—C8—C9	118.9 (2)
Zn1—N1—C2	114.32 (12)	C7—C8—H8	120.57
Zn1—N1—C3	124.61 (13)	C9—C8—H8	120.57
C2—N1—C3	121.05 (16)	C4—C9—C8	122.59 (19)
Zn1—N2—C10	115.00 (12)	N2—C10—C1	112.92 (15)
Zn1—N2—C11	127.37 (14)	N2—C10—H10a	109.47
C10—N2—C11	117.60 (17)	N2—C10—H10b	109.47
C2—C1—C10	115.44 (16)	C1—C10—H10a	109.47
C2—C1—H1a	109.47	C1—C10—H10b	109.47
C2—C1—H1b	109.47	H10a—C10—H10b	105.79
C10—C1—H1a	109.47	N2—C11—C12	122.46 (18)
C10—C1—H1b	109.47	N2—C11—H11	118.77
H1a—C1—H1b	102.77	C12—C11—H11	118.77
N1—C2—C1	111.04 (17)	C11—C12—C13	120.71 (17)
N1—C2—H2a	109.47	C11—C12—C17	122.07 (17)
N1—C2—H2b	109.47	C13—C12—C17	117.19 (18)
C1—C2—H2a	109.47	C12—C13—C14	122.22 (18)
C1—C2—H2b	109.47	C13—C14—C15	118.60 (19)
H2a—C2—H2b	107.85	C13—C14—H14	120.7
N1—C3—C4	126.59 (18)	C15—C14—H14	120.7
N1—C3—H3	116.71	C14—C15—C16	121.4 (2)
C4—C3—H3	116.71	C14—C15—H15	119.32
C3—C4—C5	121.91 (19)	C16—C15—H15	119.32
C3—C4—C9	121.04 (17)	C15—C16—C17	118.73 (19)
C5—C4—C9	117.01 (18)	C15—C16—H16	120.63
C4—C5—C6	121.7 (2)	C17—C16—H16	120.63
C5—C6—C7	119.1 (2)	C12—C17—C16	121.89 (18)

Experimental details

Crystal data
Chemical formula	[ZnBr₂(C₁₇H₁₄Cl₄N₂)]
M_r	613.3
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	17.0433 (3), 9.3216 (2), 13.6038 (2)
β (°)	97.313 (2)
V (Å³)	2143.67 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.38
Crystal size (mm)	0.33 × 0.28 × 0.10

Data collection
Diffractometer	Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.5, 1
No. of measured, independent and observed [I > 3σ(I)] reflections	32456, 5469, 4344
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.691

Refinement
R[F > 3σ(F)], wR(F), S	0.023, 0.053, 1.32
No. of reflections	5469
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.43

Computer programs: CrysAlis PRO (Agilent, 2011), SIR2002 (Burla et al., 2003), JANA2006 (Petříček et al., 2006), DIAMOND (Brandenburg & Putz, 2005).

Selected bond lengths (Å) top

Zn1—Br1	2.3599 (3)	Zn1—N1	2.0662 (16)
Zn1—Br2	2.3371 (3)	Zn1—N2	2.0628 (16)

Acknowledgements

We acknowledge the Golestan and Damghan Universities for partial support of this work, the Institutional Research Plan No. AVOZ10100521 of the Institute of Physics and the Praemium Academiae Project of the Academy of Sciences of the Czech Republic.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103. CrossRef IUCr Journals Google Scholar
Khalaj, M., Dehghanpour, S. & Mahmoudi, A. (2008). Acta Cryst. E64, m1018. Web of Science CSD CrossRef IUCr Journals Google Scholar
Khalaj, M., Dehghanpour, S., Mahmoudi, A. & Seyedidarzam, S. (2009). Acta Cryst. E65, m890. Web of Science CSD CrossRef IUCr Journals Google Scholar
Khalaji, A. D., Grivani, G., Jalali Akerdi, S., Stoeckli-Evans, H. & Das, D. (2012). J. Chem. Crystallogr. 42, 83–88. Web of Science CSD CrossRef CAS Google Scholar
Khalaji, A. D., Jalali Akerdi, S., Grivani, G., Stoeckli-Evans, H. & Das, D. (2011). Russ. J. Coord. Chem. 37, 578–584. Web of Science CrossRef CAS Google Scholar
Khalaji, A. D., Weil, M., Grivani, G. & Jalali Akerdi, S. (2010). Monatsh. Chem. 141, 539–543. Web of Science CSD CrossRef CAS Google Scholar
Komatsu, H., Ochiai, B., Hino, T. & Endo, T. (2007). J. Mol. Catal. A273, 289–297. Web of Science CrossRef Google Scholar
Montazerozohori, M., Khani, S., Tavakol, H., Hojjati, A. & Kazemi, M. (2011). Spectrochim. Acta Part A, 81, 122–127. CrossRef CAS Google Scholar
Petříček, V., Dušek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Praha, Czech Republic. Google Scholar
Salehzadeh, S., Khalaj, M., Dehghanpour, S. & Tarmoradi, I. (2011). Acta Cryst. E67, m1556. Web of Science CrossRef 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.