Bis[3-allyl-1-(4-cyanobenzyl)-2-methylbenzimidazolium] di-μ-bromido-bis[bromidocuprate(I)]

Xu, G.-H.; Wang, W.

doi:10.1107/S1600536808026937

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page m1198

doi:10.1107/S1600536808026937

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Bis[3-allyl-1-(4-cyanobenzyl)-2-methylbenzimidazolium] di-μ-bromido-bis[bromidocuprate(I)]

Guang-Hai Xu ^a and Wei Wang ^a ^*

^aOrdered Matter Science Research Center, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: seuwangwei@gmail.com

(Received 13 August 2008; accepted 20 August 2008; online 23 August 2008)

The asymmetric unit of the title compound, (C₁₉H₁₈N₃)₂[Cu₂Br₄], contains one cation and one half-anion; there is a centre of symmetry mid-way between the two Cu atoms. In the cation, the nearly planar benzimidazole ring system is oriented at dihedral angles of 75.31 (3) and 21.39 (3)° with respect to the cyanobenzyl and allyl groups, respectively. The dihedral angle between cyanobenzyl and allyl groups is 87.94 (3)°. In the crystal structure, intermolecular C—H⋯Br hydrogen bonds link the molecules. There is a C—H⋯π contact between the cyanobenzyl ring and the anion; π—π contacts also exist between the benzimidazole ring systems as well as between the anion and the cyanobenzyl ring [centroid–centroid distances = 4.024 (1) and 4.617 (1) Å, respectively].

Related literature

For related literature, see: Aaker et al. (2005 ).

Experimental

Crystal data

(C₁₉H₁₈N₃)₂[Cu₂Br₄]
M_r = 1023.44
Triclinic, $[P \overline 1]$
a = 9.6407 (5) Å
b = 10.1029 (11) Å
c = 11.0389 (6) Å
α = 87.27 (2)°
β = 69.990 (17)°
γ = 81.41 (2)°
V = 998.93 (18) Å³
Z = 2
Mo Kα radiation
μ = 5.10 mm⁻¹
T = 294 (2) K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku, SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.361, T_max = 0.375
10227 measured reflections
4517 independent reflections
2765 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.134
S = 0.97
4517 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 1.06 e Å⁻³
Δρ_min = −0.76 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯Br1ⁱ	0.97	2.90	3.863 (5)	175
C10—H10C⋯Br1	0.96	2.93	3.788 (5)	150
C17—H17A⋯Br1ⁱⁱ	0.93	2.92	3.707 (5)	143
C4—H4a⋯Cg1ⁱⁱⁱ	0.93	3.36	3.746 (2)	108 (1)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1; (iii) x, y, z-1. Cg1 is the centroid of the anion.

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2005); 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, New_Global_Publ_Block. DOI: 10.1107/S1600536808026937/hk2513sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808026937/hk2513Isup2.hkl

checkCIF report

Comment top

The asymmetric unit of the title compound contains one cation and one-half anion (Fig. 1). In the cation, rings A (N2/N3/C9/C14/C19), B (C14—C19) and C (C2—C7) are, of course, planar and the dihedral angles between them are A/B = 1.47 (3)°, A/C = 75.18 (4)° and B/C = 75.46 (4)°. So, the benzimidazole ring system is nearly planar, and it is oriented with respect to the cyanobenzyl and allyl groups at dihedral angles of 75.31 (3)° and 21.39 (3)°, respectively. The dihedral angle between cyanobenzyl and allyl groups is 87.94 (3)°.

In the crystal structure, intermolecular C—H···Br hydrogen bonds link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure. There also exists a C—H···π contact (Table 1) between the cyanobenzyl ring and the anion. The π—π contacts between the rings A and B as well as the anion and the ring C, Cg2···Cg4ⁱ and Cg3···Cg1ⁱⁱ [symmetry codes: (i) -x, 1 - y, 1 - z; (ii) x, y, z - 1, where Cg1, Cg2, Cg3 and Cg4 are centroids of the anion, the rings A, C and B, respectively] further stabilize the structure, with centroid-centroid distances of 4.024 (1) and 4.617 (1) Å, respectively.

Related literature top

For related literature, see: Aaker et al. (2005). Cg1 is the centroid of the anion.

Experimental top

The synthesis of (1) (Scheme 1) was reported, previously (Aaker et al., 2005). The mixture of (1) (2.47 g, 10 mmol), allyl bromide (1.21 g, 10 mmol) and Na₂CO₃ (0.53 g, 5 mmol) was stirred in THF (50 ml) under reflux for 24 h to obtain (2) (Scheme 1) with high yield (90%). The colorless crystals suitable for X-ray analysis were obtained from the mixture of (2) (73.6 mg, 0.2 mmol), CuBr (28.8 mg, 0.2 mmol) and methanol (2 ml) sealed in a glass tube maintaining at 353 K for 5 d.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalStructure (Rigaku/MSC, 2005); 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. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level [symmetry code: (A) -x, 1 - y, 2 - z].
	Fig. 2. A partial packing diagram of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.
	Fig. 3. The formation of the title compound.

Bis[3-allyl-1-(4-cyanobenzyl)-2-methylbenzimidazolium] di-µ-bromido-bis[bromidocuprate(I)] top

Crystal data top

(C₁₉H₁₈N₃)₂[Cu₂Br₄]	Z = 1
M_r = 1023.44	F(000) = 504
Triclinic, P1	D_x = 1.701 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6407 (5) Å	Cell parameters from 2257 reflections
b = 10.1029 (11) Å	θ = 2.8–27.5°
c = 11.0389 (6) Å	µ = 5.10 mm⁻¹
α = 87.27 (2)°	T = 294 K
β = 69.990 (17)°	Prism, colorless
γ = 81.41 (2)°	0.20 × 0.20 × 0.20 mm
V = 998.93 (18) Å³

Data collection top

Rigaku, SCXmini diffractometer	4517 independent reflections
Radiation source: fine-focus sealed tube	2765 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 2.8°
ω scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −13→13
T_min = 0.361, T_max = 0.375	l = −14→14
10227 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0636P)²] where P = (F_o² + 2F_c²)/3
4517 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 1.07 e Å⁻³
0 restraints	Δρ_min = −0.76 e Å⁻³

Crystal data top

(C₁₉H₁₈N₃)₂[Cu₂Br₄]	γ = 81.41 (2)°
M_r = 1023.44	V = 998.93 (18) Å³
Triclinic, P1	Z = 1
a = 9.6407 (5) Å	Mo Kα radiation
b = 10.1029 (11) Å	µ = 5.10 mm⁻¹
c = 11.0389 (6) Å	T = 294 K
α = 87.27 (2)°	0.20 × 0.20 × 0.20 mm
β = 69.990 (17)°

Data collection top

Rigaku, SCXmini diffractometer	4517 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2765 reflections with I > 2σ(I)
T_min = 0.361, T_max = 0.375	R_int = 0.052
10227 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 0.97	Δρ_max = 1.07 e Å⁻³
4517 reflections	Δρ_min = −0.76 e Å⁻³
226 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	0.37052 (6)	0.42643 (5)	0.73582 (5)	0.05337 (18)
Br2	−0.06239 (6)	0.34357 (6)	0.94360 (6)	0.0684 (2)
Cu1	0.14770 (8)	0.47171 (8)	0.90578 (7)	0.0703 (3)
N1	0.5950 (7)	0.0085 (5)	−0.2925 (5)	0.0873 (18)
N2	0.2273 (4)	0.3449 (4)	0.3653 (4)	0.0413 (9)
N3	0.1992 (4)	0.2221 (4)	0.5394 (3)	0.0406 (9)
C1	0.5454 (7)	0.0689 (6)	−0.1995 (6)	0.0586 (14)
C2	0.4844 (6)	0.1517 (5)	−0.0842 (5)	0.0486 (12)
C3	0.3336 (6)	0.1632 (5)	−0.0149 (5)	0.0554 (14)
H3A	0.2729	0.1148	−0.0396	0.067*
C4	0.2729 (6)	0.2476 (5)	0.0920 (5)	0.0511 (13)
H4A	0.1714	0.2562	0.1386	0.061*
C5	0.3641 (5)	0.3188 (5)	0.1291 (4)	0.0428 (11)
C6	0.5157 (5)	0.3059 (5)	0.0593 (5)	0.0522 (13)
H6A	0.5771	0.3529	0.0847	0.063*
C7	0.5758 (6)	0.2230 (6)	−0.0484 (5)	0.0551 (13)
H7A	0.6770	0.2155	−0.0960	0.066*
C8	0.2982 (6)	0.4137 (5)	0.2437 (4)	0.0468 (12)
H8A	0.3767	0.4580	0.2529	0.056*
H8B	0.2246	0.4819	0.2274	0.056*
C9	0.2985 (5)	0.2755 (5)	0.4384 (4)	0.0411 (11)
C10	0.4630 (5)	0.2599 (6)	0.4119 (5)	0.0538 (13)
H10A	0.5095	0.3072	0.3345	0.081*
H10B	0.5034	0.1667	0.4014	0.081*
H10C	0.4818	0.2959	0.4829	0.081*
C11	0.2307 (6)	0.1405 (5)	0.6424 (5)	0.0511 (12)
H11A	0.1753	0.1848	0.7243	0.061*
H11B	0.3360	0.1347	0.6301	0.061*
C12	0.1921 (7)	0.0028 (6)	0.6483 (6)	0.0634 (15)
H12A	0.2200	−0.0443	0.5713	0.076*
C13	0.1227 (9)	−0.0555 (7)	0.7528 (8)	0.105 (3)
H13C	0.0932	−0.0112	0.8314	0.126*
H13A	0.1019	−0.1421	0.7498	0.126*
C14	0.0569 (5)	0.2589 (5)	0.5305 (4)	0.0397 (10)
C15	−0.0827 (5)	0.2331 (5)	0.6120 (5)	0.0496 (12)
H15A	−0.0947	0.1818	0.6861	0.060*
C16	−0.2025 (6)	0.2887 (6)	0.5754 (5)	0.0563 (14)
H16A	−0.2980	0.2738	0.6261	0.068*
C17	−0.1844 (6)	0.3659 (5)	0.4657 (5)	0.0539 (13)
H17A	−0.2686	0.4011	0.4456	0.065*
C18	−0.0473 (5)	0.3928 (5)	0.3850 (5)	0.0497 (12)
H18A	−0.0365	0.4449	0.3114	0.060*
C19	0.0746 (5)	0.3368 (5)	0.4208 (4)	0.0404 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0453 (3)	0.0604 (3)	0.0527 (3)	−0.0150 (2)	−0.0116 (2)	0.0021 (3)
Br2	0.0466 (3)	0.0807 (4)	0.0750 (4)	−0.0173 (3)	−0.0105 (3)	−0.0237 (3)
Cu1	0.0549 (5)	0.0929 (6)	0.0560 (4)	−0.0042 (4)	−0.0119 (3)	−0.0038 (4)
N1	0.114 (5)	0.076 (4)	0.059 (3)	−0.020 (3)	−0.007 (3)	−0.020 (3)
N2	0.037 (2)	0.048 (2)	0.037 (2)	−0.0122 (17)	−0.0077 (16)	−0.0018 (18)
N3	0.040 (2)	0.047 (2)	0.035 (2)	−0.0093 (17)	−0.0115 (17)	−0.0010 (18)
C1	0.071 (4)	0.054 (3)	0.053 (3)	−0.016 (3)	−0.021 (3)	0.001 (3)
C2	0.061 (3)	0.045 (3)	0.039 (3)	−0.008 (2)	−0.015 (2)	−0.002 (2)
C3	0.068 (4)	0.058 (3)	0.052 (3)	−0.025 (3)	−0.029 (3)	0.002 (3)
C4	0.044 (3)	0.062 (3)	0.046 (3)	−0.015 (2)	−0.011 (2)	−0.004 (3)
C5	0.049 (3)	0.045 (3)	0.036 (2)	−0.016 (2)	−0.013 (2)	0.004 (2)
C6	0.039 (3)	0.070 (4)	0.049 (3)	−0.020 (2)	−0.011 (2)	−0.009 (3)
C7	0.046 (3)	0.071 (4)	0.046 (3)	−0.014 (3)	−0.010 (2)	−0.008 (3)
C8	0.051 (3)	0.049 (3)	0.038 (3)	−0.014 (2)	−0.010 (2)	−0.001 (2)
C9	0.042 (3)	0.044 (3)	0.039 (3)	−0.007 (2)	−0.014 (2)	−0.005 (2)
C10	0.037 (3)	0.072 (4)	0.053 (3)	−0.014 (2)	−0.013 (2)	−0.001 (3)
C11	0.050 (3)	0.054 (3)	0.055 (3)	−0.013 (2)	−0.023 (2)	0.009 (3)
C12	0.075 (4)	0.057 (3)	0.060 (4)	−0.007 (3)	−0.027 (3)	0.003 (3)
C13	0.132 (7)	0.075 (5)	0.116 (7)	−0.046 (5)	−0.041 (6)	0.022 (5)
C14	0.035 (2)	0.044 (3)	0.039 (3)	−0.005 (2)	−0.0107 (19)	−0.007 (2)
C15	0.039 (3)	0.056 (3)	0.046 (3)	−0.005 (2)	−0.005 (2)	−0.002 (2)
C16	0.033 (3)	0.068 (4)	0.060 (3)	−0.009 (2)	−0.002 (2)	−0.010 (3)
C17	0.043 (3)	0.059 (3)	0.062 (3)	−0.003 (2)	−0.022 (3)	−0.004 (3)
C18	0.044 (3)	0.057 (3)	0.051 (3)	−0.006 (2)	−0.019 (2)	−0.002 (3)
C19	0.038 (3)	0.040 (3)	0.042 (3)	−0.007 (2)	−0.011 (2)	−0.006 (2)

Geometric parameters (Å, º) top

Br1—Cu1	2.3181 (10)	C8—H8A	0.9700
Br2—Cu1ⁱ	2.4134 (11)	C8—H8B	0.9700
Br2—Cu1	2.4710 (10)	C9—C10	1.496 (6)
Cu1—Br2ⁱ	2.4134 (11)	C10—H10A	0.9600
Cu1—Cu1ⁱ	2.8874 (15)	C10—H10B	0.9600
N1—C1	1.136 (7)	C10—H10C	0.9600
N2—C8	1.476 (6)	C11—C12	1.486 (7)
N2—C9	1.340 (6)	C11—H11A	0.9700
N2—C19	1.401 (5)	C11—H11B	0.9700
N3—C9	1.347 (6)	C12—C13	1.285 (8)
N3—C11	1.462 (6)	C12—H12A	0.9300
N3—C14	1.402 (6)	C13—H13C	0.9300
C2—C1	1.452 (7)	C13—H13A	0.9300
C2—C3	1.381 (7)	C14—C15	1.394 (6)
C2—C7	1.381 (7)	C15—H15A	0.9300
C3—C4	1.392 (7)	C16—C15	1.384 (7)
C3—H3A	0.9300	C16—C17	1.382 (7)
C4—H4A	0.9300	C16—H16A	0.9300
C5—C4	1.385 (6)	C17—H17A	0.9300
C5—C6	1.389 (6)	C18—C17	1.376 (7)
C5—C8	1.519 (6)	C18—H18A	0.9300
C6—H6A	0.9300	C19—C14	1.387 (6)
C7—C6	1.389 (7)	C19—C18	1.398 (7)
C7—H7A	0.9300

Cu1ⁱ—Br2—Cu1	72.46 (3)	N2—C9—C10	125.1 (4)
Br1—Cu1—Br2ⁱ	129.22 (4)	N3—C9—C10	125.3 (4)
Br1—Cu1—Br2	122.83 (4)	C9—C10—H10A	109.5
Br2ⁱ—Cu1—Br2	107.54 (3)	C9—C10—H10B	109.5
Br1—Cu1—Cu1ⁱ	172.96 (5)	H10A—C10—H10B	109.5
Br2ⁱ—Cu1—Cu1ⁱ	54.69 (3)	C9—C10—H10C	109.5
Br2—Cu1—Cu1ⁱ	52.85 (3)	H10A—C10—H10C	109.5
C9—N2—C19	108.6 (4)	H10B—C10—H10C	109.5
C9—N2—C8	125.8 (4)	N3—C11—C12	113.8 (4)
C19—N2—C8	125.5 (4)	N3—C11—H11A	108.8
C9—N3—C14	108.3 (4)	C12—C11—H11A	108.8
C9—N3—C11	127.0 (4)	N3—C11—H11B	108.8
C14—N3—C11	124.8 (4)	C12—C11—H11B	108.8
N1—C1—C2	177.3 (6)	H11A—C11—H11B	107.7
C7—C2—C3	120.7 (4)	C13—C12—C11	124.3 (6)
C7—C2—C1	119.9 (5)	C13—C12—H12A	117.8
C3—C2—C1	119.4 (5)	C11—C12—H12A	117.8
C2—C3—C4	119.8 (5)	C12—C13—H13C	120.0
C2—C3—H3A	120.1	C12—C13—H13A	120.0
C4—C3—H3A	120.1	H13C—C13—H13A	120.0
C5—C4—C3	119.9 (5)	C19—C14—C15	122.2 (4)
C5—C4—H4A	120.1	C19—C14—N3	106.8 (4)
C3—C4—H4A	120.1	C15—C14—N3	130.9 (5)
C4—C5—C6	119.9 (4)	C16—C15—C14	115.7 (5)
C4—C5—C8	120.3 (4)	C16—C15—H15A	122.2
C6—C5—C8	119.8 (4)	C14—C15—H15A	122.2
C7—C6—C5	120.1 (4)	C17—C16—C15	121.9 (5)
C7—C6—H6A	119.9	C17—C16—H16A	119.0
C5—C6—H6A	119.9	C15—C16—H16A	119.0
C2—C7—C6	119.6 (5)	C18—C17—C16	122.9 (5)
C2—C7—H7A	120.2	C18—C17—H17A	118.5
C6—C7—H7A	120.2	C16—C17—H17A	118.5
N2—C8—C5	112.7 (4)	C17—C18—C19	115.6 (5)
N2—C8—H8A	109.0	C17—C18—H18A	122.2
C5—C8—H8A	109.0	C19—C18—H18A	122.2
N2—C8—H8B	109.0	C14—C19—C18	121.6 (4)
C5—C8—H8B	109.0	C14—C19—N2	106.7 (4)
H8A—C8—H8B	107.8	C18—C19—N2	131.7 (4)
N2—C9—N3	109.6 (4)

Cu1ⁱ—Br2—Cu1—Br1	−173.22 (6)	C7—C2—C3—C4	0.1 (8)
Cu1ⁱ—Br2—Cu1—Br2ⁱ	0.0	C1—C2—C7—C6	177.6 (5)
C9—N2—C8—C5	79.9 (6)	C3—C2—C7—C6	0.7 (8)
C19—N2—C8—C5	−97.3 (5)	C2—C3—C4—C5	−0.5 (8)
C8—N2—C9—N3	−177.6 (4)	C6—C5—C4—C3	0.1 (8)
C19—N2—C9—N3	0.0 (5)	C8—C5—C4—C3	178.5 (5)
C8—N2—C9—C10	2.5 (7)	C4—C5—C6—C7	0.7 (8)
C19—N2—C9—C10	−179.9 (4)	C8—C5—C6—C7	−177.7 (5)
C8—N2—C19—C14	177.4 (4)	C4—C5—C8—N2	61.6 (6)
C9—N2—C19—C14	−0.2 (5)	C6—C5—C8—N2	−119.9 (5)
C8—N2—C19—C18	−3.9 (8)	C2—C7—C6—C5	−1.1 (8)
C9—N2—C19—C18	178.5 (5)	N3—C11—C12—C13	−135.1 (7)
C11—N3—C9—N2	−179.4 (4)	N3—C14—C15—C16	178.1 (5)
C14—N3—C9—N2	0.2 (5)	C19—C14—C15—C16	0.8 (7)
C11—N3—C9—C10	0.5 (7)	C15—C16—C17—C18	0.2 (8)
C14—N3—C9—C10	−179.9 (5)	C17—C16—C15—C14	−0.6 (8)
C9—N3—C11—C12	−117.9 (5)	N2—C19—C14—N3	0.3 (5)
C14—N3—C11—C12	62.6 (6)	N2—C19—C14—C15	178.1 (4)
C9—N3—C14—C15	−177.9 (5)	C18—C19—C14—N3	−178.5 (4)
C11—N3—C14—C15	1.7 (8)	C18—C19—C14—C15	−0.7 (7)
C9—N3—C14—C19	−0.3 (5)	C19—C18—C17—C16	0.0 (8)
C11—N3—C14—C19	179.3 (4)	N2—C19—C18—C17	−178.3 (5)
C1—C2—C3—C4	−176.8 (5)	C14—C19—C18—C17	0.2 (7)

Symmetry code: (i) −x, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···Br1ⁱⁱ	0.97	2.90	3.863 (5)	175
C10—H10C···Br1	0.96	2.93	3.788 (5)	150
C17—H17A···Br1ⁱⁱⁱ	0.93	2.92	3.707 (5)	143
C4—H4a···Cg1^iv	0.93	3.36	3.746 (2)	108 (1)

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

Experimental details

Crystal data
Chemical formula	(C₁₉H₁₈N₃)₂[Cu₂Br₄]
M_r	1023.44
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	9.6407 (5), 10.1029 (11), 11.0389 (6)
α, β, γ (°)	87.27 (2), 69.990 (17), 81.41 (2)
V (Å³)	998.93 (18)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	5.10
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku, SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.361, 0.375
No. of measured, independent and observed [I > 2σ(I)] reflections	10227, 4517, 2765
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.134, 0.97
No. of reflections	4517
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.07, −0.76

Computer programs: CrystalClear (Rigaku/MSC, 2005), CrystalStructure (Rigaku/MSC, 2005), 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
C8—H8A···Br1ⁱ	0.97	2.90	3.863 (5)	175.0
C10—H10C···Br1	0.96	2.93	3.788 (5)	149.9
C17—H17A···Br1ⁱⁱ	0.93	2.92	3.707 (5)	143.4
C4—H4a···Cg1ⁱⁱⁱ	0.93	3.36	3.746 (2)	107.5 (2)

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

Acknowledgements

The authors are grateful to the Starter Fund of Southeast University for financial support to purchase the CCD X-ray diffractometer.

References

Aaker, C. B., Desper, J. & Urbinam, J. F. (2005). Cryst. Growth Des. 5, 1283–1293. Google Scholar
Rigaku/MSC. (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 9| September 2008| Page m1198

doi:10.1107/S1600536808026937

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

Bis[3-allyl-1-(4-cyano­benzyl)-2-methylbenzimidazolium] di-μ-bromido-bis­[bromidocuprate(I)]

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis[3-allyl-1-(4-cyanobenzyl)-2-methylbenzimidazolium] di-μ-bromido-bis[bromidocuprate(I)]