Bis(2,4,6-trimethyl­pyridinium) tetra­bromidozincate

Ali, B.F.; Haddad, S.F.; Al-Far, R.

doi:10.1107/S1600536812040925

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page m1320

doi:10.1107/S1600536812040925

Open

access

Bis(2,4,6-trimethylpyridinium) tetrabromidozincate

Basem F. Ali,^a ^* Salim F. Haddad ^b and Rawhi Al-Far ^c

^aDepartment of Chemistry, Al al-Bayt University, Mafraq 25113, Jordan, ^bDepartment of Chemistry, The University of Jordan, Amman 11942, Jordan, and ^cFaculty of Science and IT, Al-Balqa'a Applied University, Salt, Jordan
^*Correspondence e-mail: bfali@aabu.edu.jo

(Received 26 September 2012; accepted 28 September 2012; online 3 October 2012)

In the title compound, (C₈H₁₂N)₂[ZnBr₄], the coordination geometry of the anion is approximately tetrahedral. The Zn—Br bond lengths range from 2.3901 (19) to 2.449 (2) Å and the Br—Zn—Br angles range from 107.09 (8) to 112.48 (8)°. In the crystal, each [ZnBr₄]²⁻ anion is connected to four cations through two N—H⋯Br and two C—H⋯Br hydrogen bonds, forming two-dimensional ⋯(cation)₂⋯anion⋯(cation₂)⋯ sheets parallel to the bc plane. Within each sheet, the anions are arranged in stacks with no significant inter-anion Br⋯Br interactions [the shortest being > 4.3 Å], while the cations are in chains, with weak π–π stacking interactions [centroid–centroid distance = 3.991 Å] between cations interacting with the same anion.

Related literature

For background information, see: Ali & Al-Far (2009 ). For bond lengths and angles in the [ZnBr₄]²⁻ anion, see: Ali & Al-Far (2009); Peng & Li (2011 ). For another structure containing the 2,4,6-trimethylpyridinium cation, see: Abbasi et al. (2011 ).

Experimental

Crystal data

(C₈H₁₂N)₂[ZnBr₄]
M_r = 629.36
Triclinic, P 1
a = 7.3627 (8) Å
b = 9.0310 (8) Å
c = 9.1854 (9) Å
α = 101.741 (8)°
β = 110.778 (10)°
γ = 96.321 (8)°
V = 547.89 (9) Å³
Z = 1
Mo Kα radiation
μ = 8.41 mm⁻¹
T = 293 K
0.35 × 0.25 × 0.20 mm

Data collection

Oxford Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.413, T_max = 1.000
3637 measured reflections
2730 independent reflections
2399 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.140
S = 1.02
2730 reflections
214 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.77 e Å⁻³
Absolute structure: Flack (1983 ), 797 Friedel pairs
Flack parameter: −0.02 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Br1ⁱ	0.86	2.79	3.647 (13)	175
N2—H2A⋯Br3	0.86	2.57	3.433 (10)	179
C2—H2B⋯Br3	0.93	2.79	3.685 (11)	162
C10—H10A⋯Br4ⁱⁱ	0.93	2.86	3.776 (13)	168
Symmetry codes: (i) x-1, y-1, z-1; (ii) x, y+1, z+1.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812040925/pv2593sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812040925/pv2593Isup2.hkl

checkCIF report

Comment top

In connection with ongoing studies of the structural aspects of halo-metal anion salts (Ali & Al-Far, 2009), we herein report the crystal structure of the title compound. The asymmetric unit contains an anion and two independent cations (Fig. 1). The geometry of ZnBr₄^2- anion is approximately tetrahedral. In the anion, the bond distances and angles fall in the range of those reported previously (Peng & Li, 2011). In the cations, the bond lengths and angles are within normal ranges compared to the salt containing 2,4,6-trimethylpyridinium cation (Abbasi et al., 2011). The packing of the structure can be regarded as alternating stacks of anions and chains of cations. The anion stacks are parallel to the cation chains, with no significant Br···Br interactions [shortest Br···Br interactions being greater than 4.3 Å]. The anions and cations are interacting significantly through two N—H···Br—Zn and two pyC—H···Br—Zn hydrogen bonding (Table 1). These interactions link anions and cations into two-dimensional sheets of etc ···(cation)₂···anion···(cation)₂···etc parallel to bc plane (Fig. 2).

Related literature top

For background information, see: Ali & Al-Far (2009). For bond lengths and angles in the [ZnBr₄]^2- anion, see: Ali & Al-Far (2009); Peng & Li (2011). For another structure containing the 2,4,6-trimethylpyridinium cation, see: Abbasi et al. (2011).

Experimental top

To a hot solution of 2,4,6-trimethylpyridine (0.122 g, 1 mmol) and 1 ml of 60% HBr dissolved in 95% EtOH (15 ml), a hot solution of ZnCl₂ (0.136 g, 1 mmol) dissolved in 95% EtOH (10 ml) was added. The resulting mixture was then treated with liquid Br₂ (2 ml) and refluxed for 2 h. The resulting mixture was left undisturbed to evaporate at room temperature whereupon colorless plate crystals were formed after two days.

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: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the asymmetric unit of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A packing diagram of the title compound showing alternating stacks of anions and cations. C/N—H···Br interactions are shown as dashed lines.

Bis(2,4,6-trimethylpyridinium) tetrabromidozincate top

Crystal data top

(C₈H₁₂N)₂[ZnBr₄]	Z = 1
M_r = 629.36	F(000) = 304
Triclinic, P1	D_x = 1.908 Mg m⁻³
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3627 (8) Å	Cell parameters from 1674 reflections
b = 9.0310 (8) Å	θ = 2.9–29.1°
c = 9.1854 (9) Å	µ = 8.41 mm⁻¹
α = 101.741 (8)°	T = 293 K
β = 110.778 (10)°	Chunk, colourless
γ = 96.321 (8)°	0.35 × 0.25 × 0.2 mm
V = 547.89 (9) Å³

Data collection top

Oxford Xcalibur Eos diffractometer	2730 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2399 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
Detector resolution: 16.0534 pixels mm^-1	θ_max = 25.0°, θ_min = 2.9°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −10→7
T_min = 0.413, T_max = 1.000	l = −10→10
3637 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.140	w = 1/[σ²(F_o²) + (0.0933P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2730 reflections	Δρ_max = 0.75 e Å⁻³
214 parameters	Δρ_min = −0.77 e Å⁻³
3 restraints	Absolute structure: Flack (1983), 797 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (2)

Crystal data top

(C₈H₁₂N)₂[ZnBr₄]	γ = 96.321 (8)°
M_r = 629.36	V = 547.89 (9) Å³
Triclinic, P1	Z = 1
a = 7.3627 (8) Å	Mo Kα radiation
b = 9.0310 (8) Å	µ = 8.41 mm⁻¹
c = 9.1854 (9) Å	T = 293 K
α = 101.741 (8)°	0.35 × 0.25 × 0.2 mm
β = 110.778 (10)°

Data collection top

Oxford Xcalibur Eos diffractometer	2730 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2399 reflections with I > 2σ(I)
T_min = 0.413, T_max = 1.000	R_int = 0.021
3637 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.140	Δρ_max = 0.75 e Å⁻³
S = 1.02	Δρ_min = −0.77 e Å⁻³
2730 reflections	Absolute structure: Flack (1983), 797 Friedel pairs
214 parameters	Absolute structure parameter: −0.02 (2)
3 restraints

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
Zn1	0.9260 (2)	0.39402 (17)	0.49611 (17)	0.0439 (3)
Br4	0.9532 (2)	0.27784 (15)	0.24750 (16)	0.0629 (4)
Br3	0.59389 (18)	0.45209 (17)	0.43497 (16)	0.0576 (4)
Br2	0.9650 (2)	0.22617 (15)	0.67076 (16)	0.0609 (4)
Br1	1.16750 (19)	0.63427 (15)	0.62829 (16)	0.0617 (4)
N2	0.6828 (15)	0.6293 (11)	0.8284 (12)	0.046 (2)
H2A	0.6588	0.5839	0.7298	0.055*
C10	0.7852 (19)	0.8528 (16)	1.0355 (17)	0.053 (3)
H10A	0.8271	0.9595	1.0719	0.063*
C13	0.6550 (18)	0.5429 (14)	0.9227 (15)	0.047 (3)
C9	0.7459 (19)	0.7828 (15)	0.8773 (18)	0.052 (3)
C12	0.7024 (18)	0.6132 (16)	1.0853 (15)	0.053 (3)
H12A	0.6917	0.5538	1.1546	0.064*
C11	0.7654 (18)	0.7721 (14)	1.1426 (16)	0.045 (3)
N1	0.2717 (18)	−0.1748 (16)	0.0480 (15)	0.065 (3)
H1A	0.2518	−0.2148	−0.0511	0.078*
C4	0.2765 (16)	−0.1995 (15)	0.3001 (15)	0.046 (3)
H4A	0.2619	−0.2619	0.3658	0.056*
C2	0.3449 (17)	0.0429 (13)	0.2619 (15)	0.045 (3)
H2B	0.3782	0.1497	0.3019	0.054*
C5	0.2520 (17)	−0.2679 (15)	0.1393 (14)	0.045 (3)
C3	0.3220 (18)	−0.0405 (15)	0.3603 (15)	0.047 (3)
C1	0.323 (2)	−0.0168 (17)	0.1074 (18)	0.058 (3)
C15	0.804 (2)	0.848 (2)	1.3147 (17)	0.067 (4)
H15A	0.9121	0.8130	1.3848	0.100*
H15B	0.6876	0.8221	1.3356	0.100*
H15C	0.8381	0.9580	1.3338	0.100*
C7	0.350 (2)	0.038 (2)	0.5270 (19)	0.062 (4)
H7A	0.4814	0.0996	0.5823	0.093*
H7B	0.3321	−0.0378	0.5830	0.093*
H7C	0.2547	0.1030	0.5239	0.093*
C14	0.774 (3)	0.864 (2)	0.758 (2)	0.083 (5)
H14A	0.8654	0.8205	0.7171	0.125*
H14B	0.8253	0.9715	0.8091	0.125*
H14C	0.6487	0.8504	0.6700	0.125*
C8	0.202 (2)	−0.4391 (14)	0.0714 (18)	0.057 (3)
H8A	0.1790	−0.4631	−0.0411	0.086*
H8B	0.0841	−0.4806	0.0842	0.086*
H8C	0.3094	−0.4835	0.1277	0.086*
C16	0.585 (3)	0.3720 (16)	0.851 (2)	0.064 (4)
H16A	0.6220	0.3414	0.7604	0.097*
H16B	0.4432	0.3467	0.8150	0.097*
H16C	0.6444	0.3188	0.9303	0.097*
C6	0.353 (4)	0.090 (3)	0.010 (3)	0.120 (9)
H6A	0.2549	0.1531	−0.0043	0.179*
H6B	0.3405	0.0304	−0.0941	0.179*
H6C	0.4828	0.1540	0.0641	0.179*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0515 (8)	0.0429 (7)	0.0372 (7)	0.0055 (6)	0.0178 (6)	0.0109 (5)
Br4	0.0890 (11)	0.0564 (9)	0.0506 (8)	0.0112 (7)	0.0382 (8)	0.0105 (6)
Br3	0.0525 (8)	0.0733 (9)	0.0461 (7)	0.0155 (7)	0.0172 (6)	0.0155 (6)
Br2	0.0802 (10)	0.0601 (8)	0.0521 (8)	0.0160 (7)	0.0292 (7)	0.0279 (7)
Br1	0.0650 (9)	0.0521 (8)	0.0573 (9)	−0.0076 (6)	0.0207 (7)	0.0073 (6)
N2	0.055 (6)	0.047 (6)	0.029 (5)	−0.006 (5)	0.012 (4)	0.012 (4)
C10	0.042 (6)	0.048 (7)	0.061 (9)	0.009 (5)	0.013 (6)	0.009 (6)
C13	0.047 (7)	0.037 (6)	0.053 (7)	0.002 (5)	0.019 (6)	0.007 (6)
C9	0.051 (7)	0.047 (8)	0.059 (8)	0.007 (6)	0.020 (6)	0.018 (6)
C12	0.049 (7)	0.070 (9)	0.041 (7)	0.016 (7)	0.017 (6)	0.015 (6)
C11	0.036 (6)	0.051 (8)	0.047 (7)	0.009 (5)	0.016 (5)	0.008 (6)
N1	0.059 (7)	0.094 (10)	0.044 (6)	0.012 (6)	0.020 (5)	0.021 (6)
C4	0.041 (6)	0.062 (8)	0.040 (6)	0.017 (6)	0.016 (5)	0.018 (6)
C2	0.047 (7)	0.029 (6)	0.051 (8)	0.003 (5)	0.011 (6)	0.010 (5)
C5	0.035 (6)	0.069 (8)	0.030 (6)	0.011 (5)	0.010 (5)	0.013 (6)
C3	0.045 (7)	0.058 (8)	0.037 (6)	0.015 (6)	0.014 (5)	0.007 (6)
C1	0.051 (8)	0.064 (9)	0.058 (9)	0.007 (6)	0.014 (6)	0.031 (7)
C15	0.064 (9)	0.082 (11)	0.037 (8)	0.007 (8)	0.018 (7)	−0.014 (7)
C7	0.066 (10)	0.074 (10)	0.048 (8)	0.020 (8)	0.027 (7)	0.009 (7)
C14	0.109 (14)	0.086 (12)	0.073 (12)	0.029 (10)	0.035 (10)	0.057 (10)
C8	0.070 (9)	0.037 (7)	0.061 (9)	0.006 (6)	0.024 (7)	0.009 (6)
C16	0.087 (11)	0.049 (8)	0.065 (10)	0.000 (7)	0.039 (8)	0.021 (7)
C6	0.120 (17)	0.15 (2)	0.119 (19)	0.027 (15)	0.047 (15)	0.101 (17)

Geometric parameters (Å, º) top

Zn1—Br2	2.3901 (19)	C2—C1	1.356 (19)
Zn1—Br4	2.398 (2)	C2—H2B	0.9300
Zn1—Br1	2.4270 (19)	C5—C8	1.494 (18)
Zn1—Br3	2.449 (2)	C3—C7	1.480 (19)
N2—C13	1.329 (16)	C1—C6	1.49 (2)
N2—C9	1.340 (16)	C15—H15A	0.9600
N2—H2A	0.8600	C15—H15B	0.9600
C10—C9	1.37 (2)	C15—H15C	0.9600
C10—C11	1.38 (2)	C7—H7A	0.9600
C10—H10A	0.9300	C7—H7B	0.9600
C13—C12	1.397 (18)	C7—H7C	0.9600
C13—C16	1.501 (18)	C14—H14A	0.9600
C9—C14	1.50 (2)	C14—H14B	0.9600
C12—C11	1.387 (18)	C14—H14C	0.9600
C12—H12A	0.9300	C8—H8A	0.9600
C11—C15	1.498 (18)	C8—H8B	0.9600
N1—C5	1.333 (18)	C8—H8C	0.9600
N1—C1	1.377 (19)	C16—H16A	0.9600
N1—H1A	0.8600	C16—H16B	0.9600
C4—C3	1.385 (17)	C16—H16C	0.9600
C4—C5	1.418 (17)	C6—H6A	0.9600
C4—H4A	0.9300	C6—H6B	0.9600
C2—C3	1.331 (18)	C6—H6C	0.9600

Br2—Zn1—Br4	112.48 (8)	C2—C1—N1	117.5 (12)
Br2—Zn1—Br1	110.92 (8)	C2—C1—C6	119.3 (16)
Br4—Zn1—Br1	109.19 (7)	N1—C1—C6	123.1 (16)
Br2—Zn1—Br3	107.09 (8)	C11—C15—H15A	109.5
Br4—Zn1—Br3	108.55 (8)	C11—C15—H15B	109.5
Br1—Zn1—Br3	108.49 (8)	H15A—C15—H15B	109.5
C13—N2—C9	124.2 (11)	C11—C15—H15C	109.5
C13—N2—H2A	117.9	H15A—C15—H15C	109.5
C9—N2—H2A	117.9	H15B—C15—H15C	109.5
C9—C10—C11	122.8 (12)	C3—C7—H7A	109.5
C9—C10—H10A	118.6	C3—C7—H7B	109.5
C11—C10—H10A	118.6	H7A—C7—H7B	109.5
N2—C13—C12	118.9 (11)	C3—C7—H7C	109.5
N2—C13—C16	118.0 (11)	H7A—C7—H7C	109.5
C12—C13—C16	123.1 (12)	H7B—C7—H7C	109.5
N2—C9—C10	116.9 (12)	C9—C14—H14A	109.5
N2—C9—C14	117.8 (13)	C9—C14—H14B	109.5
C10—C9—C14	125.2 (14)	H14A—C14—H14B	109.5
C11—C12—C13	119.6 (12)	C9—C14—H14C	109.5
C11—C12—H12A	120.2	H14A—C14—H14C	109.5
C13—C12—H12A	120.2	H14B—C14—H14C	109.5
C10—C11—C12	117.4 (12)	C5—C8—H8A	109.5
C10—C11—C15	123.1 (12)	C5—C8—H8B	109.5
C12—C11—C15	119.5 (13)	H8A—C8—H8B	109.5
C5—N1—C1	122.0 (12)	C5—C8—H8C	109.5
C5—N1—H1A	119.0	H8A—C8—H8C	109.5
C1—N1—H1A	119.0	H8B—C8—H8C	109.5
C3—C4—C5	120.7 (12)	C13—C16—H16A	109.5
C3—C4—H4A	119.7	C13—C16—H16B	109.5
C5—C4—H4A	119.7	H16A—C16—H16B	109.5
C3—C2—C1	124.6 (12)	C13—C16—H16C	109.5
C3—C2—H2B	117.7	H16A—C16—H16C	109.5
C1—C2—H2B	117.7	H16B—C16—H16C	109.5
N1—C5—C4	118.0 (12)	C1—C6—H6A	109.5
N1—C5—C8	120.4 (12)	C1—C6—H6B	109.5
C4—C5—C8	121.6 (12)	H6A—C6—H6B	109.5
C2—C3—C4	117.0 (11)	C1—C6—H6C	109.5
C2—C3—C7	119.7 (12)	H6A—C6—H6C	109.5
C4—C3—C7	123.3 (13)	H6B—C6—H6C	109.5

C9—N2—C13—C12	−3.1 (18)	C1—N1—C5—C4	2.9 (19)
C9—N2—C13—C16	−179.7 (13)	C1—N1—C5—C8	−178.3 (13)
C13—N2—C9—C10	0.6 (19)	C3—C4—C5—N1	−0.8 (17)
C13—N2—C9—C14	178.8 (13)	C3—C4—C5—C8	−179.6 (12)
C11—C10—C9—N2	1 (2)	C1—C2—C3—C4	1.3 (19)
C11—C10—C9—C14	−177.0 (14)	C1—C2—C3—C7	179.9 (13)
N2—C13—C12—C11	3.9 (18)	C5—C4—C3—C2	−1.3 (17)
C16—C13—C12—C11	−179.7 (13)	C5—C4—C3—C7	−179.8 (12)
C9—C10—C11—C12	−0.1 (19)	C3—C2—C1—N1	1 (2)
C9—C10—C11—C15	−178.8 (13)	C3—C2—C1—C6	−180.0 (15)
C13—C12—C11—C10	−2.4 (17)	C5—N1—C1—C2	−3 (2)
C13—C12—C11—C15	176.3 (12)	C5—N1—C1—C6	177.8 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Br1ⁱ	0.86	2.79	3.647 (13)	175
N2—H2A···Br3	0.86	2.57	3.433 (10)	179
C2—H2B···Br3	0.93	2.79	3.685 (11)	162
C10—H10A···Br4ⁱⁱ	0.93	2.86	3.776 (13)	168

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

Experimental details

Crystal data
Chemical formula	(C₈H₁₂N)₂[ZnBr₄]
M_r	629.36
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.3627 (8), 9.0310 (8), 9.1854 (9)
α, β, γ (°)	101.741 (8), 110.778 (10), 96.321 (8)
V (Å³)	547.89 (9)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	8.41
Crystal size (mm)	0.35 × 0.25 × 0.2

Data collection
Diffractometer	Oxford Xcalibur Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.413, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	3637, 2730, 2399
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.140, 1.02
No. of reflections	2730
No. of parameters	214
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.75, −0.77
Absolute structure	Flack (1983), 797 Friedel pairs
Absolute structure parameter	−0.02 (2)

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Br1ⁱ	0.86	2.79	3.647 (13)	175.4
N2—H2A···Br3	0.86	2.57	3.433 (10)	178.7
C2—H2B···Br3	0.93	2.79	3.685 (11)	162.2
C10—H10A···Br4ⁱⁱ	0.93	2.86	3.776 (13)	167.7

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

Acknowledgements

This structure was determined at the Hamdi Mango Center for Scientific Research at the University of Jordan, Amman. RA-F is grateful for financial support from Al-Balqa'a Applied University (Salt, Jordan).

References

Abbasi, M. A., Nazir, K., Akkurt, M., Aziz-ur-Rehman, Khan, I. U. & Mustafa, G. (2011). Acta Cryst. E67, o2375. Web of Science CSD CrossRef IUCr Journals Google Scholar
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Ali, B. F. & Al-Far, R. (2009). Acta Cryst. E65, m581–m582. Web of Science CSD CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Peng, C. & Li, Y. (2011). Acta Cryst. E67, m1056. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar