Bis(benzyl-trimethyl-ammonium) tetra-bromidocuprate(II).

In the title mol-ecular salt, (C(10)H(16)N)(2)[CuBr(4)], the Cu(II) ion adopts a squashed tetra-hedral geometry with Br-Cu-Br angles varying between 99.29 (3) and 132.53 (3)°. In the crystal, the components are linked by C-H⋯Br inter-actions, thereby generating a three-dimensional network.

Related literature

For background to mol­ecular–ionic compounds, see: Coffey et al. (2000 ▶); Liu et al. (2001 ▶); Long et al. (1997 ▶); Luque et al. (1997 ▶); Woodward et al. (2001 ▶).

Experimental

Crystal data

(C10H16N)2[CuBr4]

M = 683.66

Orthorhombic,

a = 9.1908 (8) Å

b = 9.6697 (19) Å

c = 29.0243 (8) Å

V = 2579.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 7.05 mm−1

T = 291 K

0.28 × 0.26 × 0.24 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.161, T max = 0.183

25511 measured reflections

5922 independent reflections

3769 reflections with I > 2σ(I)

R int = 0.101

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.172

S = 1.02

5922 reflections

250 parameters

H-atom parameters constrained

Δρmax = 0.89 e Å−3

Δρmin = −1.33 e Å−3

Absolute structure: Flack (1983 ▶), 2556 Friedel pairs

Flack parameter: 0.06 (2)

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811034830/hb6385sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034830/hb6385Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C10H16N)2[CuBr4]	F(000) = 1340
Mr = 683.66	Dx = 1.760 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 20422 reflections
a = 9.1908 (8) Å	θ = 3.1–27.8°
b = 9.6697 (19) Å	µ = 7.05 mm−1
c = 29.0243 (8) Å	T = 291 K
V = 2579.5 (6) Å3	Block, purple
Z = 4	0.28 × 0.26 × 0.24 mm

Rigaku Mercury2 diffractometer	5922 independent reflections
Radiation source: fine-focus sealed tube	3769 reflections with I > 2σ(I)
graphite	Rint = 0.101
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
CCD_Profile_fitting scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −12→12
Tmin = 0.161, Tmax = 0.183	l = −37→37
25511 measured reflections

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)] = 0.063	H-atom parameters constrained
wR(F2) = 0.172	w = 1/[σ2(Fo2) + (0.0838P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
5922 reflections	Δρmax = 0.89 e Å−3
250 parameters	Δρmin = −1.33 e Å−3
0 restraints	Absolute structure: Flack (1983), 2556 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.06 (2)

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.

	x	y	z	Uiso*/Ueq
Br1	0.16703 (6)	0.33426 (5)	0.800673 (18)	0.06775 (16)
Br2	0.49529 (5)	0.46102 (5)	0.855426 (17)	0.05492 (13)
Br3	0.48651 (5)	0.08709 (5)	0.870934 (18)	0.05845 (14)
Br4	0.15255 (6)	0.21832 (6)	0.91811 (2)	0.07334 (17)
C1	0.5435 (5)	0.2722 (7)	0.73255 (16)	0.077 (2)
H1A	0.4986	0.3359	0.7115	0.115*
H1B	0.5080	0.2889	0.7631	0.115*
H1C	0.5203	0.1792	0.7236	0.115*
C2	0.7333 (6)	0.4347 (5)	0.74409 (16)	0.0749 (18)
H2A	0.6761	0.4959	0.7254	0.112*
H2B	0.8348	0.4530	0.7391	0.112*
H2C	0.7100	0.4493	0.7760	0.112*
C3	0.7683 (5)	0.1951 (6)	0.76459 (15)	0.0680 (17)
H3A	0.7392	0.2194	0.7953	0.102*
H3B	0.8723	0.2005	0.7621	0.102*
H3C	0.7371	0.1025	0.7579	0.102*
C4	0.7539 (4)	0.2631 (4)	0.68414 (13)	0.0441 (12)
H4A	0.6950	0.3158	0.6627	0.053*
H4B	0.7387	0.1659	0.6775	0.053*
C5	0.9108 (4)	0.2968 (4)	0.67551 (13)	0.0351 (11)
C6	0.9473 (5)	0.4283 (5)	0.65858 (15)	0.0537 (14)
H6	0.8759	0.4939	0.6524	0.064*
C7	1.0959 (6)	0.4577 (5)	0.65128 (17)	0.0684 (17)
H7	1.1235	0.5444	0.6405	0.082*
C8	1.1977 (5)	0.3617 (6)	0.65970 (15)	0.0683 (17)
H8	1.2945	0.3852	0.6547	0.082*
C9	1.1682 (5)	0.2327 (5)	0.67503 (15)	0.0569 (14)
H9	1.2420	0.1687	0.6803	0.068*
C10	1.0156 (4)	0.1981 (4)	0.68298 (14)	0.0474 (12)
H10	0.9897	0.1101	0.6930	0.057*
C11	0.8707 (5)	0.5105 (5)	0.91952 (14)	0.0533 (14)
H11A	0.9518	0.4566	0.9089	0.080*
H11B	0.9034	0.6016	0.9276	0.080*
H11C	0.7992	0.5168	0.8955	0.080*
C12	0.9205 (5)	0.4376 (6)	0.99779 (15)	0.0609 (16)
H12A	0.8770	0.4072	1.0261	0.091*
H12B	0.9617	0.5279	1.0020	0.091*
H12C	0.9956	0.3740	0.9889	0.091*
C13	0.7555 (5)	0.3076 (5)	0.95072 (16)	0.0596 (16)
H13A	0.6932	0.3096	0.9242	0.089*
H13B	0.7022	0.2728	0.9767	0.089*
H13C	0.8372	0.2485	0.9447	0.089*
C14	0.6765 (5)	0.5276 (4)	0.97618 (16)	0.0482 (13)
H14A	0.6285	0.4785	1.0010	0.058*
H14B	0.6080	0.5347	0.9509	0.058*
C15	0.7132 (4)	0.6732 (4)	0.99279 (15)	0.0426 (12)
C16	0.7364 (5)	0.6983 (5)	1.03985 (15)	0.0567 (15)
H16	0.7287	0.6280	1.0616	0.068*
C17	0.7715 (6)	0.8337 (6)	1.05265 (17)	0.0758 (18)
H17	0.7846	0.8544	1.0837	0.091*
C18	0.7868 (5)	0.9352 (5)	1.0209 (2)	0.0659 (17)
H18	0.8184	1.0222	1.0302	0.079*
C19	0.7564 (5)	0.9120 (6)	0.9752 (2)	0.0732 (18)
H19	0.7613	0.9844	0.9542	0.088*
C20	0.7181 (5)	0.7791 (5)	0.96046 (16)	0.0584 (15)
H20	0.6963	0.7620	0.9297	0.070*
Cu1	0.32377 (5)	0.27605 (5)	0.861735 (16)	0.03655 (13)
N1	0.7012 (3)	0.2913 (3)	0.73160 (12)	0.0441 (10)
N2	0.8055 (3)	0.4434 (3)	0.96042 (12)	0.0401 (10)

	U11	U22	U33	U12	U13	U23
Br1	0.0715 (3)	0.0703 (3)	0.0614 (3)	0.0008 (3)	−0.0305 (3)	0.0075 (3)
Br2	0.0561 (2)	0.0591 (3)	0.0496 (3)	−0.0083 (2)	0.0004 (2)	−0.0010 (2)
Br3	0.0548 (2)	0.0547 (2)	0.0659 (3)	0.0217 (2)	0.0048 (2)	−0.0025 (2)
Br4	0.0754 (3)	0.0813 (3)	0.0634 (3)	0.0056 (3)	0.0165 (3)	−0.0031 (3)
C1	0.040 (2)	0.150 (5)	0.040 (3)	−0.008 (3)	0.004 (2)	−0.014 (3)
C2	0.108 (4)	0.060 (3)	0.057 (3)	−0.015 (3)	0.033 (3)	−0.026 (2)
C3	0.068 (3)	0.096 (4)	0.040 (3)	0.007 (3)	0.008 (3)	0.006 (3)
C4	0.0396 (19)	0.054 (2)	0.039 (2)	−0.002 (2)	0.0012 (19)	−0.012 (2)
C5	0.0446 (19)	0.036 (2)	0.025 (2)	−0.0101 (18)	0.0075 (17)	−0.0088 (17)
C6	0.069 (3)	0.054 (3)	0.038 (3)	−0.006 (2)	0.015 (2)	0.004 (2)
C7	0.104 (4)	0.052 (3)	0.050 (3)	−0.021 (3)	0.016 (3)	0.004 (2)
C8	0.056 (3)	0.109 (4)	0.040 (3)	−0.035 (3)	0.010 (2)	−0.009 (3)
C9	0.053 (2)	0.082 (3)	0.037 (3)	−0.007 (3)	−0.005 (2)	0.000 (2)
C10	0.043 (2)	0.053 (2)	0.047 (2)	−0.004 (2)	0.019 (2)	−0.003 (2)
C11	0.070 (3)	0.056 (2)	0.034 (2)	−0.005 (2)	0.003 (2)	0.012 (2)
C12	0.059 (3)	0.089 (3)	0.035 (3)	0.021 (3)	−0.017 (2)	−0.003 (3)
C13	0.061 (3)	0.053 (3)	0.065 (3)	0.001 (2)	0.000 (3)	−0.002 (2)
C14	0.041 (2)	0.059 (3)	0.045 (3)	−0.002 (2)	−0.002 (2)	−0.004 (2)
C15	0.036 (2)	0.043 (2)	0.048 (3)	−0.0017 (19)	−0.0012 (19)	−0.005 (2)
C16	0.070 (3)	0.062 (3)	0.038 (3)	0.003 (3)	−0.002 (2)	−0.004 (2)
C17	0.107 (4)	0.074 (3)	0.046 (3)	0.024 (3)	−0.010 (3)	−0.021 (3)
C18	0.056 (3)	0.045 (3)	0.096 (4)	0.001 (2)	0.006 (3)	−0.020 (3)
C19	0.084 (3)	0.061 (3)	0.075 (4)	0.005 (3)	0.024 (3)	0.017 (3)
C20	0.078 (3)	0.056 (3)	0.041 (3)	0.020 (3)	0.003 (2)	0.001 (2)
Cu1	0.0384 (2)	0.0409 (2)	0.0304 (3)	0.0049 (2)	−0.0006 (2)	−0.0023 (2)
N1	0.0378 (17)	0.0514 (19)	0.043 (2)	−0.0065 (17)	0.0017 (15)	−0.0093 (17)
N2	0.0329 (16)	0.0449 (19)	0.042 (2)	−0.0031 (16)	−0.0029 (15)	−0.0020 (16)

Cu1—Br1	2.3522 (7)	C9—H9	0.9300
Cu1—Br2	2.3912 (7)	C10—H10	0.9300
Cu1—Br3	2.3764 (7)	C11—N2	1.480 (5)
Cu1—Br4	2.3378 (7)	C11—H11A	0.9600
C1—N1	1.461 (5)	C11—H11B	0.9600
C1—H1A	0.9600	C11—H11C	0.9600
C1—H1B	0.9600	C12—N2	1.515 (5)
C1—H1C	0.9600	C12—H12A	0.9600
C2—N1	1.463 (6)	C12—H12B	0.9600
C2—H2A	0.9600	C12—H12C	0.9600
C2—H2B	0.9600	C13—N2	1.420 (6)
C2—H2C	0.9600	C13—H13A	0.9600
C3—N1	1.471 (6)	C13—H13B	0.9600
C3—H3A	0.9600	C13—H13C	0.9600
C3—H3B	0.9600	C14—N2	1.509 (5)
C3—H3C	0.9600	C14—C15	1.525 (6)
C4—N1	1.485 (5)	C14—H14A	0.9700
C4—C5	1.499 (5)	C14—H14B	0.9700
C4—H4A	0.9700	C15—C20	1.390 (6)
C4—H4B	0.9700	C15—C16	1.403 (6)
C5—C10	1.374 (5)	C16—C17	1.398 (7)
C5—C6	1.404 (6)	C16—H16	0.9300
C6—C7	1.411 (7)	C17—C18	1.353 (7)
C6—H6	0.9300	C17—H17	0.9300
C7—C8	1.340 (7)	C18—C19	1.373 (8)
C7—H7	0.9300	C18—H18	0.9300
C8—C9	1.352 (7)	C19—C20	1.400 (7)
C8—H8	0.9300	C19—H19	0.9300
C9—C10	1.460 (6)	C20—H20	0.9300
Br4—Cu1—Br1	99.92 (3)	N2—C11—H11C	109.5
Br4—Cu1—Br3	99.29 (3)	H11A—C11—H11C	109.5
Br1—Cu1—Br3	130.85 (3)	H11B—C11—H11C	109.5
Br4—Cu1—Br2	132.53 (3)	N2—C12—H12A	109.5
Br1—Cu1—Br2	99.62 (3)	N2—C12—H12B	109.5
Br3—Cu1—Br2	99.72 (3)	H12A—C12—H12B	109.5
N1—C1—H1A	109.5	N2—C12—H12C	109.5
N1—C1—H1B	109.5	H12A—C12—H12C	109.5
H1A—C1—H1B	109.5	H12B—C12—H12C	109.5
N1—C1—H1C	109.5	N2—C13—H13A	109.5
H1A—C1—H1C	109.5	N2—C13—H13B	109.5
H1B—C1—H1C	109.5	H13A—C13—H13B	109.5
N1—C2—H2A	109.5	N2—C13—H13C	109.5
N1—C2—H2B	109.5	H13A—C13—H13C	109.5
H2A—C2—H2B	109.5	H13B—C13—H13C	109.5
N1—C2—H2C	109.5	N2—C14—C15	114.8 (3)
H2A—C2—H2C	109.5	N2—C14—H14A	108.6
H2B—C2—H2C	109.5	C15—C14—H14A	108.6
N1—C3—H3A	109.5	N2—C14—H14B	108.6
N1—C3—H3B	109.5	C15—C14—H14B	108.6
H3A—C3—H3B	109.5	H14A—C14—H14B	107.5
N1—C3—H3C	109.5	C20—C15—C16	121.6 (4)
H3A—C3—H3C	109.5	C20—C15—C14	118.3 (4)
H3B—C3—H3C	109.5	C16—C15—C14	120.1 (4)
N1—C4—C5	115.4 (3)	C17—C16—C15	117.1 (4)
N1—C4—H4A	108.4	C17—C16—H16	121.4
C5—C4—H4A	108.4	C15—C16—H16	121.4
N1—C4—H4B	108.4	C18—C17—C16	121.5 (5)
C5—C4—H4B	108.4	C18—C17—H17	119.3
H4A—C4—H4B	107.5	C16—C17—H17	119.3
C10—C5—C6	121.1 (4)	C17—C18—C19	121.2 (5)
C10—C5—C4	119.8 (4)	C17—C18—H18	119.4
C6—C5—C4	119.0 (4)	C19—C18—H18	119.4
C5—C6—C7	117.8 (4)	C18—C19—C20	119.8 (5)
C5—C6—H6	121.1	C18—C19—H19	120.1
C7—C6—H6	121.1	C20—C19—H19	120.1
C8—C7—C6	120.6 (5)	C15—C20—C19	118.5 (4)
C8—C7—H7	119.7	C15—C20—H20	120.7
C6—C7—H7	119.7	C19—C20—H20	120.7
C7—C8—C9	124.1 (5)	C1—N1—C2	108.4 (4)
C7—C8—H8	118.0	C1—N1—C3	108.9 (4)
C9—C8—H8	118.0	C2—N1—C3	110.7 (4)
C8—C9—C10	117.1 (4)	C1—N1—C4	108.6 (3)
C8—C9—H9	121.4	C2—N1—C4	109.7 (3)
C10—C9—H9	121.4	C3—N1—C4	110.5 (3)
C5—C10—C9	119.3 (4)	C13—N2—C11	112.2 (3)
C5—C10—H10	120.3	C13—N2—C14	107.8 (3)
C9—C10—H10	120.3	C11—N2—C14	108.9 (3)
N2—C11—H11A	109.5	C13—N2—C12	109.5 (3)
N2—C11—H11B	109.5	C11—N2—C12	107.9 (3)
H11A—C11—H11B	109.5	C14—N2—C12	110.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Br3i	0.93	2.90	3.737 (5)	150
C12—H12A···Br4ii	0.96	2.89	3.781 (5)	155
C12—H12C···Br4iii	0.96	2.93	3.794 (5)	151

Table 1

Selected bond lengths (Å)

Cu1—Br1	2.3522 (7)
Cu1—Br2	2.3912 (7)
Cu1—Br3	2.3764 (7)
Cu1—Br4	2.3378 (7)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯Br3i	0.93	2.90	3.737 (5)	150
C12—H12A⋯Br4ii	0.96	2.89	3.781 (5)	155
C12—H12C⋯Br4iii	0.96	2.93	3.794 (5)	151

Symmetry codes: (i) ; (ii) ; (iii) .