Bis­(2-amino-6-methyl­pyridinium) tetra­bromido­cuprate(II)

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

doi:10.1107/S1600536808010647

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Pages m689-m690

doi:10.1107/S1600536808010647

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Bis(2-amino-6-methylpyridinium) tetrabromidocuprate(II)

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

^aFaculty of Information Technology and Science, Al-Balqa'a Applied University, Salt, Jordan, ^bDepartment of Chemistry, Al al-Bayt University, Mafraq 25113, Jordan, and ^cDepartment of Chemistry, The University of Jordan, Amman, Jordan
^*Correspondence e-mail: rohi@bau.edu.jo

(Received 15 April 2008; accepted 17 April 2008; online 23 April 2008)

In the crystal structure of the title compound, (C₆H₉N₂)₂[CuBr₄], the geometry around the Cu atom is intermediate between tetrahedral (T_d) and square planar (D_4h). Each [CuBr₄]²⁻ anion is connected non-symmetrically to four surrounding cations through N—H⋯X (pyridine and amine proton) hydrogen bonds, forming chains of the ladder-type running parallel to the crystallographic b axis. These layers are further connected by means of offset face-to-face interactions (parallel to the a axis), giving a three-dimensional network. Cation π–π stacking [centroid separations of 3.69 (9) and 3.71 (1) Å] and Br⋯aryl interactions [3.72 (2) and 4.04 (6) Å] are present in the crystal structure. There are no intermolecular Br⋯Br interactions.

Related literature

For related literature, see: Al-Far & Ali (2007a ,b ); Ali & Al-Far (2007 , 2008 ); Allen et al. (1987 , 1997 ); Desiraju & Steiner (1999 ); Dolling et al. (2001 ); Haddad et al. (2006 ); Hunter (1994 ); Panunto et al. (1987 ); Raithby et al. (2000 ); Robinson et al. (2000 ); Luque et al. (2001 ).

Experimental

Crystal data

(C₆H₉N₂)₂[CuBr₄]
M_r = 601.45
Triclinic, $[P \overline 1]$
a = 7.9238 (9) Å
b = 8.2521 (11) Å
c = 15.2916 (18) Å
α = 78.472 (11)°
β = 82.839 (10)°
γ = 89.947 (14)°
V = 971.8 (2) Å³
Z = 2
Mo Kα radiation
μ = 9.35 mm⁻¹
T = 293 (2) K
0.20 × 0.15 × 0.10 mm

Data collection

Bruker P4 diffractometer
Absorption correction: ψ scan (XSCANS; Bruker, 1996 )T_min = 0.199, T_max = 0.392
4381 measured reflections
3567 independent reflections
2018 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.153
S = 1.00
3567 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Br1—Cu1	2.3848 (14)
Cu1—Br2	2.3575 (16)
Cu1—Br4	2.3713 (14)
Cu1—Br3	2.3765 (16)

Br2—Cu1—Br4	101.27 (6)
Br2—Cu1—Br3	132.23 (7)
Br4—Cu1—Br3	100.99 (6)
Br2—Cu1—Br1	98.36 (6)
Br4—Cu1—Br1	129.74 (7)
Br3—Cu1—Br1	98.93 (6)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Br3ⁱ	0.86	2.47	3.324 (7)	172
N8—H8⋯Br1	0.86	2.52	3.367 (8)	170
N9—H9B⋯Br4ⁱⁱ	0.86	2.64	3.487 (10)	168
N2—H2B⋯Br2ⁱⁱⁱ	0.86	2.73	3.547 (9)	158
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) x-1, y, z; (iii) -x+1, -y+1, -z+2.

Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 2008 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010647/at2561sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808010647/at2561Isup2.hkl

checkCIF report

Comment top

Non-covalent interactions play an important role in organizing structural units in both natural and artificial systems. They exercise important effects on the organization and properties of many materials in areas such as biology (Hunter 1994; Desiraju & Steiner 1999), crystal engineering (see for example: Allen et al.,1997; Dolling et al., 2001) and material science (Panunto et al., 1987; Robinson et al., 2000). The interactions governing the crystal organization are expected to affect the packing and then the specific properties of solids. In connection with ongoing studies (Ali & Al-Far, 2008; Ali & Al-Far, 2007; Al-Far & Ali, 2007a,b) of the structural aspects of halo-metal anion salts, we herein report the crystal structure of title compound (I) along with its crystal supramolecularity.

The asymmetric unit in (I) contains one anion and two cations (Fig. 1). The Cu—Br distances are similar, but Cu—Br2 that is engaged in longest hydrogen bonding is shorter than the others (Table 2). The Cu—Br bond distances fall in the range of bond distances reported previously for compounds containing Cu—Br anions (Luque et al., 2001; Raithby et al., 2000; Haddad et al., 2006). The bond angles are present in two distinguished sets. The first contains four angles in the range 98.36 (6) - 101.27 (6)° which are much lower than the other set which contains two angles 129.74 (7) and 132.23 (7)°. Accordingly the geometry of CuBr₄^2- anion is an intermediate between regular tetrahedral (T_d) and square planar (D_4h) (Table 2).

The cation bond lengths and angles are within expected range (Allen et al. 1987), with the cations (type A contains N1 and type B contains N8) being of course planar.

In the structure (Fig. 2), each anion is connected nonsymmetrically to four cations interacting via N—H···Br and HN—H···Br hydrogen bonding, Table 3, forming chains of the ladder type run approximately parallel to the crystallographic b-axis. The cations type A represnt the rungs while both cations type B and anions represent the rails of a ladder (Fig. 3).

There are no Br···Br interactions were observed (shortest being 4.6651 (17) Å). Cations π···π stacking (in a-ditrection) is observed, with significant ones being X1A···X1A [2 - x, 2 - y, 2 - z] and X1B···X1B [- x, 1 - y, 1 - z] of 3.69 (9) and 3.71 (1), respectively. Also Br···aryl interactions present by the unusually short Br(1) [-x, 2 - y, 1 - z]···X1B contact of 3.72 (2) Å and the longer Br(3)···X1A of 4.04 (6) Å contact.

Related literature top

For related literature, see: Al-Far & Ali (2007a,b); Ali & Al-Far (2007, 2008); Allen et al. (1987, 1997); Desiraju & Steiner (1999); Dolling et al. (2001); Haddad et al. (2006); Hunter (1994); Panunto et al. (1987); Raithby et al. (2000); Robinson et al. (2000); Luque et al. (2001).

Experimental top

To a warm solution of 2-amino-6-methylpyridine (2 mmol) dissolved in 10 ml absolute ethanol acidified with 3 ml 60% HBr, CuBr₂ (1 mmol) dissolved in 10 ml absolute ethanol was added. The resulting solution was then treated with 2 ml of Br_{2 (}_l₎. The mixture was refluxed for 2 h. The mixture was then allowed to stand and evaporate slowly at room temperature. In two days time, block blue crystals were formed and filtered (yield, 86.5%). A single-crystal suitable for diffraction measurements were chosen and used for data collection.

Computing details top

Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS (Bruker, 1996); data reduction: SHELXTL (Sheldrick, 2008); 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 (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Anion···cation intermolecular interactions between one anion and four surrounding cations. N—H···Br—Cu intermolecular interactions are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding omitted for clarity.
	Fig. 3. A packing diagram of (I), shows chains of the ladder type run approximately parallel to the crystallographic b-axis. Hydrogen atoms omitted for clarity.

bis(2-amino-6-methylpyridinium) tetrabromidocuprate(II) top

Crystal data top

(C₆H₉N₂)₂[CuBr₄]	Z = 2
M_r = 601.45	F(000) = 574
Triclinic, P1	D_x = 2.056 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9238 (9) Å	Cell parameters from 298 reflections
b = 8.2521 (11) Å	θ = 2.2–27.5°
c = 15.2916 (18) Å	µ = 9.35 mm⁻¹
α = 78.472 (11)°	T = 293 K
β = 82.839 (10)°	Block, blue
γ = 89.947 (14)°	0.20 × 0.15 × 0.10 mm
V = 971.8 (2) Å³

Data collection top

Bruker P4 diffractometer	3567 independent reflections
Radiation source: fine-focus sealed tube	2018 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
Detector resolution: 3 pixels mm^-1	θ_max = 25.5°, θ_min = 2.5°
ω scans	h = −9→1
Absorption correction: ψ scan (PROGRAM; REF (YEAR)	k = −9→9
T_min = 0.199, T_max = 0.392	l = −18→18
4381 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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0724P)²] where P = (F_o² + 2F_c²)/3
3567 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.65 e Å⁻³

Crystal data top

(C₆H₉N₂)₂[CuBr₄]	γ = 89.947 (14)°
M_r = 601.45	V = 971.8 (2) Å³
Triclinic, P1	Z = 2
a = 7.9238 (9) Å	Mo Kα radiation
b = 8.2521 (11) Å	µ = 9.35 mm⁻¹
c = 15.2916 (18) Å	T = 293 K
α = 78.472 (11)°	0.20 × 0.15 × 0.10 mm
β = 82.839 (10)°

Data collection top

Bruker P4 diffractometer	3567 independent reflections
Absorption correction: ψ scan (PROGRAM; REF (YEAR)	2018 reflections with I > 2σ(I)
T_min = 0.199, T_max = 0.392	R_int = 0.053
4381 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.00	Δρ_max = 0.57 e Å⁻³
3567 reflections	Δρ_min = −0.65 e Å⁻³
190 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
Br1	0.18757 (14)	0.94944 (11)	0.69574 (7)	0.0597 (3)
Cu1	0.32354 (14)	0.69646 (13)	0.74711 (8)	0.0442 (3)
N1	0.6876 (10)	1.0718 (9)	1.0416 (6)	0.052 (2)
H1	0.6292	1.1120	1.0832	0.062*
Br2	0.08231 (15)	0.54289 (13)	0.82710 (9)	0.0745 (4)
N2	0.6864 (13)	0.8282 (10)	1.1440 (6)	0.074 (3)
H2A	0.6268	0.8750	1.1825	0.089*
H2B	0.7143	0.7266	1.1591	0.089*
C2	0.7347 (13)	0.9116 (12)	1.0624 (7)	0.052 (3)
Br3	0.56567 (13)	0.80573 (15)	0.79499 (8)	0.0679 (4)
C3	0.8257 (13)	0.8462 (13)	0.9938 (8)	0.060 (3)
H3	0.8594	0.7368	1.0049	0.072*
Br4	0.45192 (14)	0.50445 (13)	0.66438 (8)	0.0650 (4)
C4	0.8653 (14)	0.9439 (17)	0.9100 (8)	0.073 (4)
H4	0.9239	0.9006	0.8636	0.087*
C5	0.8171 (15)	1.1093 (15)	0.8947 (7)	0.070 (3)
H5	0.8487	1.1761	0.8384	0.084*
C6	0.7270 (14)	1.1742 (12)	0.9585 (7)	0.058 (3)
C7	0.6683 (17)	1.3493 (13)	0.9503 (9)	0.089 (4)
H7C	0.7028	1.4097	0.8902	0.134*
H7B	0.7180	1.4007	0.9923	0.134*
H7A	0.5465	1.3491	0.9630	0.134*
N8	0.0896 (10)	0.7845 (9)	0.5235 (5)	0.049 (2)
H8	0.1279	0.8242	0.5653	0.059*
C9	−0.0722 (12)	0.7230 (11)	0.5402 (7)	0.049 (2)
N9	−0.1600 (12)	0.7226 (11)	0.6204 (7)	0.080 (3)
H9A	−0.1137	0.7608	0.6603	0.095*
H9B	−0.2629	0.6841	0.6322	0.095*
C10	−0.1360 (13)	0.6650 (11)	0.4711 (8)	0.057 (3)
H10	−0.2473	0.6239	0.4788	0.068*
C11	−0.0343 (14)	0.6690 (12)	0.3923 (8)	0.057 (3)
H11	−0.0771	0.6302	0.3461	0.069*
C12	0.1301 (15)	0.7289 (12)	0.3794 (7)	0.062 (3)
H12	0.1968	0.7290	0.3249	0.074*
C13	0.1985 (13)	0.7888 (11)	0.4451 (7)	0.052 (3)
C14	0.3706 (14)	0.8601 (14)	0.4410 (8)	0.075 (3)
H14A	0.3823	0.8923	0.4969	0.112*
H14B	0.3878	0.9553	0.3929	0.112*
H14C	0.4538	0.7792	0.4306	0.112*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0758 (8)	0.0456 (6)	0.0583 (7)	0.0137 (5)	−0.0121 (6)	−0.0101 (5)
Cu1	0.0410 (7)	0.0451 (6)	0.0453 (7)	0.0029 (5)	0.0001 (5)	−0.0096 (5)
N1	0.049 (5)	0.058 (5)	0.050 (6)	−0.003 (4)	0.005 (4)	−0.023 (4)
Br2	0.0557 (7)	0.0607 (7)	0.0916 (10)	−0.0022 (5)	0.0223 (7)	0.0021 (6)
N2	0.116 (9)	0.060 (5)	0.045 (6)	0.010 (5)	−0.009 (6)	−0.003 (5)
C2	0.067 (7)	0.050 (6)	0.046 (7)	0.015 (5)	−0.013 (6)	−0.018 (5)
Br3	0.0443 (6)	0.1028 (9)	0.0670 (8)	−0.0010 (6)	−0.0037 (6)	−0.0441 (7)
C3	0.052 (7)	0.067 (7)	0.071 (9)	0.000 (5)	−0.013 (6)	−0.034 (7)
Br4	0.0553 (7)	0.0640 (7)	0.0793 (9)	0.0006 (5)	0.0101 (6)	−0.0345 (6)
C4	0.050 (7)	0.125 (11)	0.061 (9)	0.010 (7)	−0.010 (6)	−0.060 (8)
C5	0.076 (8)	0.100 (9)	0.035 (7)	0.001 (7)	−0.010 (6)	−0.013 (6)
C6	0.063 (7)	0.063 (6)	0.044 (7)	−0.002 (5)	−0.010 (6)	−0.003 (5)
C7	0.091 (10)	0.069 (8)	0.098 (11)	0.009 (7)	0.000 (8)	0.001 (7)
N8	0.050 (5)	0.055 (5)	0.045 (5)	0.008 (4)	−0.009 (4)	−0.014 (4)
C9	0.037 (6)	0.049 (5)	0.059 (7)	0.009 (4)	−0.002 (5)	−0.010 (5)
N9	0.058 (6)	0.108 (8)	0.080 (8)	−0.007 (5)	0.009 (6)	−0.048 (6)
C10	0.048 (6)	0.053 (6)	0.069 (8)	0.010 (5)	−0.020 (6)	−0.001 (6)
C11	0.057 (7)	0.070 (7)	0.049 (7)	0.007 (6)	−0.022 (6)	−0.011 (5)
C12	0.079 (9)	0.070 (7)	0.035 (6)	0.017 (6)	−0.005 (6)	−0.005 (5)
C13	0.055 (6)	0.042 (5)	0.053 (7)	0.003 (5)	0.002 (6)	0.001 (5)
C14	0.050 (7)	0.091 (8)	0.075 (9)	−0.006 (6)	0.008 (6)	−0.006 (7)

Geometric parameters (Å, º) top

Br1—Cu1	2.3848 (14)	C7—H7B	0.9600
Cu1—Br2	2.3575 (16)	C7—H7A	0.9600
Cu1—Br4	2.3713 (14)	N8—C9	1.355 (12)
Cu1—Br3	2.3765 (16)	N8—C13	1.382 (12)
N1—C2	1.360 (11)	N8—H8	0.8600
N1—C6	1.377 (13)	C9—N9	1.331 (13)
N1—H1	0.8600	C9—C10	1.391 (14)
N2—C2	1.310 (13)	N9—H9A	0.8600
N2—H2A	0.8600	N9—H9B	0.8600
N2—H2B	0.8600	C10—C11	1.359 (14)
C2—C3	1.396 (13)	C10—H10	0.9300
C3—C4	1.371 (16)	C11—C12	1.370 (15)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.399 (15)	C12—C13	1.371 (14)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.335 (14)	C13—C14	1.475 (14)
C5—H5	0.9300	C14—H14A	0.9600
C6—C7	1.504 (13)	C14—H14B	0.9600
C7—H7C	0.9600	C14—H14C	0.9600

Br2—Cu1—Br4	101.27 (6)	C6—C7—H7A	109.5
Br2—Cu1—Br3	132.23 (7)	H7C—C7—H7A	109.5
Br4—Cu1—Br3	100.99 (6)	H7B—C7—H7A	109.5
Br2—Cu1—Br1	98.36 (6)	C9—N8—C13	125.5 (9)
Br4—Cu1—Br1	129.74 (7)	C9—N8—H8	117.2
Br3—Cu1—Br1	98.93 (6)	C13—N8—H8	117.2
C2—N1—C6	124.6 (8)	N9—C9—N8	118.6 (10)
C2—N1—H1	117.7	N9—C9—C10	124.3 (10)
C6—N1—H1	117.7	N8—C9—C10	117.1 (9)
C2—N2—H2A	120.0	C9—N9—H9A	120.0
C2—N2—H2B	120.0	C9—N9—H9B	120.0
H2A—N2—H2B	120.0	H9A—N9—H9B	120.0
N2—C2—N1	117.9 (9)	C11—C10—C9	119.4 (10)
N2—C2—C3	124.8 (9)	C11—C10—H10	120.3
N1—C2—C3	117.3 (10)	C9—C10—H10	120.3
C4—C3—C2	119.8 (10)	C10—C11—C12	121.3 (10)
C4—C3—H3	120.1	C10—C11—H11	119.4
C2—C3—H3	120.1	C12—C11—H11	119.4
C3—C4—C5	119.5 (10)	C11—C12—C13	121.6 (10)
C3—C4—H4	120.3	C11—C12—H12	119.2
C5—C4—H4	120.3	C13—C12—H12	119.2
C6—C5—C4	122.0 (11)	C12—C13—N8	115.1 (10)
C6—C5—H5	119.0	C12—C13—C14	128.1 (11)
C4—C5—H5	119.0	N8—C13—C14	116.8 (10)
C5—C6—N1	116.8 (10)	C13—C14—H14A	109.5
C5—C6—C7	126.9 (11)	C13—C14—H14B	109.5
N1—C6—C7	116.3 (9)	H14A—C14—H14B	109.5
C6—C7—H7C	109.5	C13—C14—H14C	109.5
C6—C7—H7B	109.5	H14A—C14—H14C	109.5
H7C—C7—H7B	109.5	H14B—C14—H14C	109.5

C6—N1—C2—N2	−179.2 (10)	C13—N8—C9—N9	177.8 (9)
C6—N1—C2—C3	−1.6 (15)	C13—N8—C9—C10	−2.5 (13)
N2—C2—C3—C4	178.1 (11)	N9—C9—C10—C11	−179.0 (10)
N1—C2—C3—C4	0.7 (15)	N8—C9—C10—C11	1.4 (13)
C2—C3—C4—C5	1.4 (16)	C9—C10—C11—C12	0.1 (15)
C3—C4—C5—C6	−2.8 (17)	C10—C11—C12—C13	−0.6 (16)
C4—C5—C6—N1	1.9 (17)	C11—C12—C13—N8	−0.3 (14)
C4—C5—C6—C7	179.9 (11)	C11—C12—C13—C14	−178.6 (10)
C2—N1—C6—C5	0.3 (16)	C9—N8—C13—C12	2.0 (14)
C2—N1—C6—C7	−177.9 (9)	C9—N8—C13—C14	−179.5 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Br3ⁱ	0.86	2.47	3.324 (7)	172
N8—H8···Br1	0.86	2.52	3.367 (8)	170
N9—H9B···Br4ⁱⁱ	0.86	2.64	3.487 (10)	168
N2—H2B···Br2ⁱⁱⁱ	0.86	2.73	3.547 (9)	158

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

Experimental details

Crystal data
Chemical formula	(C₆H₉N₂)₂[CuBr₄]
M_r	601.45
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.9238 (9), 8.2521 (11), 15.2916 (18)
α, β, γ (°)	78.472 (11), 82.839 (10), 89.947 (14)
V (Å³)	971.8 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	9.35
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Bruker P4 diffractometer
Absorption correction	ψ scan (PROGRAM; REF (YEAR)
T_min, T_max	0.199, 0.392
No. of measured, independent and observed [I > 2σ(I)] reflections	4381, 3567, 2018
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.153, 1.00
No. of reflections	3567
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.65

Computer programs: XSCANS (Bruker, 1996), SHELXTL (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Br1—Cu1	2.3848 (14)	Cu1—Br4	2.3713 (14)
Cu1—Br2	2.3575 (16)	Cu1—Br3	2.3765 (16)

Br2—Cu1—Br4	101.27 (6)	Br2—Cu1—Br1	98.36 (6)
Br2—Cu1—Br3	132.23 (7)	Br4—Cu1—Br1	129.74 (7)
Br4—Cu1—Br3	100.99 (6)	Br3—Cu1—Br1	98.93 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Br3ⁱ	0.86	2.47	3.324 (7)	172.1
N8—H8···Br1	0.86	2.52	3.367 (8)	170.3
N9—H9B···Br4ⁱⁱ	0.86	2.64	3.487 (10)	167.5
N2—H2B···Br2ⁱⁱⁱ	0.86	2.73	3.547 (9)	158.0

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

Acknowledgements

Al al-Bayt University and Al-Balqa'a Applied University are thanked for financial support.

References

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