Bromidotetra­kis­(2-isopropyl-1H-imidazole-κN3)copper(II) bromide

Godlewska, S.; Socha, J.; Baranowska, K.; Dołęga, A.

doi:10.1107/S1600536811035215

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page m1338

https://doi.org/10.1107/S1600536811035215

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Bromidotetrakis(2-isopropyl-1H-imidazole-κN³)copper(II) bromide

Sylwia Godlewska,^a Joanna Socha,^a Katarzyna Baranowska ^a and Anna Dołęga ^a ^*

^aDepartment of Inorganic Chemistry, Faculty of Chemistry, Gdansk University of Technology, 11/12 G. Narutowicz St, 80952 – PL Gdańsk, Poland
^*Correspondence e-mail: anndoleg@pg.gda.pl

(Received 26 August 2011; accepted 29 August 2011; online 14 September 2011)

The Cu^II atom in the title salt, [CuBr(C₆H₁₀N₂)₄]Br, is coordinated in a square-pyramidal geometry by four imidazole N atoms and one bromide anion that is located at the apex of the pyramid. The cations and the anions form a two-dimensional network parallel to (001) through N—H⋯Br hydrogen bonds.

Related literature

For similar compounds, see: Hossaini Sadr et al. (2004 ); Li et al. (2007 ); Liu et al. (2007 ).

Experimental

Crystal data

[CuBr(C₆H₁₀N₂)₄]Br
M_r = 664
Monoclinic, P 2₁ /c
a = 10.7094 (7) Å
b = 19.9917 (6) Å
c = 16.7885 (19) Å
β = 121.552 (7)°
V = 3063.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 3.35 mm⁻¹
T = 120 K
0.41 × 0.25 × 0.23 mm

Data collection

Oxford Diffraction Xcalibur Sapphire2 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.628, T_max = 1
11133 measured reflections
5710 independent reflections
4597 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.092
S = 1.05
5710 reflections
324 parameters
H-atom parameters constrained
Δρ_max = 1.86 e Å⁻³
Δρ_min = −1.04 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯Br2	0.88	2.48	3.358 (2)	175
N4—H4A⋯Br2ⁱ	0.88	2.48	3.342 (2)	167
N6—H6D⋯Br2ⁱⁱ	0.88	2.53	3.351 (2)	155
N8—H8A⋯Br2ⁱⁱⁱ	0.88	2.49	3.362 (2)	169
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x-1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811035215/ng5221sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811035215/ng5221Isup2.hkl

checkCIF report

Comment top

Title compound was synthesized as a substrate for further synthesis of mixed ligand copper complexes.

The structure of the complex ion in (I) is similar to those described earlier (Hossaini Sadr et al. (2004); Li et al. (2007); Liu et al. (2007)). However, Cu1—Br1 bond in (I) [2.6608 (6) Å] is significantly shorter compared to the Cu1—Br1 bond found in bromotetrakis(1H-imidazole-κN³)copper(II) bromide [2.755 (1) Å] (Hossaini Sadr et al. (2004)). The steric hindrance introduced with the isopropyl group causes the rotation of the planes of imidazole rings and the hydrogen bond formed by Br1 in (1H-imidazole-κN³)copper(II) bromide is no longer present in (I). This obviously results in the strengthening and shortening of Cu1—Br1. The two-dimensional hydrogen bonding network in (I) consists of four NH···Br hydrogen bonds formed by Br2.

The structure of (I) is shown in Fig. 1 and crystal packing diagram is presented in Fig.2.

Related literature top

For similar compounds, see: Hossaini Sadr et al. (2004); Li et al. (2007); Liu et al. (2007).

Experimental top

Compound (I) was prepared by the reaction of 2-isopropylimidazole (0.496 g, 4.5 mmol) with CuBr₂ (0.223 g, 1 mmol) in methanol and slow evaporation of solvent from the reaction solution.

Structure description top

Title compound was synthesized as a substrate for further synthesis of mixed ligand copper complexes.

The structure of (I) is shown in Fig. 1 and crystal packing diagram is presented in Fig.2.

For similar compounds, see: Hossaini Sadr et al. (2004); Li et al. (2007); Liu et al. (2007).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. A view of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms of isopropyl groups have been omitted. Hydrogen bonds indicated with dashed lines.
	Fig. 2. The packing of (I) along the c axis. H atoms of isopropyl groups have been omitted. Hydrogen bonds indicated with dashed lines.

Bromidotetrakis(2-isopropyl-1H-imidazole-κN³)copper(II) bromide top

Crystal data top

[CuBr(C₆H₁₀N₂)₄]Br	F(000) = 1356
M_r = 664	D_x = 1.44 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4456 reflections
a = 10.7094 (7) Å	θ = 2.5–30.0°
b = 19.9917 (6) Å	µ = 3.35 mm⁻¹
c = 16.7885 (19) Å	T = 120 K
β = 121.552 (7)°	Prism, blue
V = 3063.0 (4) Å³	0.41 × 0.25 × 0.23 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Sapphire2 diffractometer	5710 independent reflections
Graphite monochromator	4597 reflections with I > 2σ(I)
Detector resolution: 8.1883 pixels mm^-1	R_int = 0.017
ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	h = −12→11
T_min = 0.628, T_max = 1	k = −14→24
11133 measured reflections	l = −18→20

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0602P)²] where P = (F_o² + 2F_c²)/3
5710 reflections	(Δ/σ)_max = 0.001
324 parameters	Δρ_max = 1.86 e Å⁻³
0 restraints	Δρ_min = −1.04 e Å⁻³

Crystal data top

[CuBr(C₆H₁₀N₂)₄]Br	V = 3063.0 (4) Å³
M_r = 664	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.7094 (7) Å	µ = 3.35 mm⁻¹
b = 19.9917 (6) Å	T = 120 K
c = 16.7885 (19) Å	0.41 × 0.25 × 0.23 mm
β = 121.552 (7)°

Data collection top

Oxford Diffraction Xcalibur Sapphire2 diffractometer	5710 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	4597 reflections with I > 2σ(I)
T_min = 0.628, T_max = 1	R_int = 0.017
11133 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.05	Δρ_max = 1.86 e Å⁻³
5710 reflections	Δρ_min = −1.04 e Å⁻³
324 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.31171 (3)	0.779079 (15)	0.001639 (19)	0.02020 (10)
Cu1	0.45146 (4)	0.766296 (16)	0.18655 (2)	0.01437 (10)
N1	0.6390 (3)	0.71702 (11)	0.21910 (16)	0.0171 (5)
N2	0.8002 (3)	0.64385 (13)	0.23226 (17)	0.0223 (6)
H2A	0.8388	0.6095	0.22	0.027*
N3	0.5719 (3)	0.85202 (11)	0.22788 (16)	0.0161 (5)
N4	0.7488 (3)	0.92415 (12)	0.26694 (17)	0.0215 (6)
H4A	0.8168	0.9478	0.2654	0.026*
N5	0.3114 (2)	0.81177 (11)	0.21723 (16)	0.0157 (5)
N6	0.1974 (3)	0.88848 (12)	0.24787 (17)	0.0219 (6)
H6D	0.1516	0.926	0.2444	0.026*
N7	0.3763 (3)	0.67785 (11)	0.20488 (16)	0.0176 (5)
N8	0.2343 (3)	0.60629 (12)	0.21834 (18)	0.0247 (6)
H8A	0.1554	0.5839	0.206	0.03*
C1	0.7738 (3)	0.73116 (15)	0.2985 (2)	0.0209 (7)
H1	0.7924	0.7669	0.3406	0.025*
C2	0.8743 (3)	0.68637 (15)	0.3069 (2)	0.0233 (7)
H2	0.9752	0.6847	0.3544	0.028*
C3	0.6587 (3)	0.66308 (14)	0.1806 (2)	0.0179 (6)
C4	0.5460 (3)	0.62848 (14)	0.0936 (2)	0.0194 (6)
H4	0.4525	0.6542	0.0673	0.023*
C5	0.5900 (4)	0.62837 (17)	0.0204 (2)	0.0294 (8)
H5A	0.6099	0.6743	0.0098	0.044*
H5B	0.5099	0.6097	−0.0382	0.044*
H5C	0.6782	0.6011	0.0428	0.044*
C6	0.5164 (4)	0.55681 (15)	0.1124 (2)	0.0303 (8)
H6A	0.6051	0.5298	0.1354	0.046*
H6B	0.4365	0.5373	0.0544	0.046*
H6C	0.4885	0.5576	0.1595	0.046*
C7	0.6050 (3)	0.88407 (14)	0.3097 (2)	0.0194 (6)
H7	0.5584	0.8759	0.3438	0.023*
C8	0.7131 (3)	0.92847 (15)	0.3338 (2)	0.0229 (7)
H8	0.7562	0.9571	0.3867	0.028*
C9	0.6617 (3)	0.87732 (14)	0.2031 (2)	0.0174 (6)
C10	0.6682 (3)	0.86072 (15)	0.1187 (2)	0.0220 (7)
H10	0.6014	0.8219	0.0865	0.026*
C11	0.8215 (4)	0.84085 (19)	0.1435 (3)	0.0378 (9)
H11A	0.8889	0.8783	0.1749	0.057*
H11B	0.8203	0.8294	0.0864	0.057*
H11C	0.8543	0.802	0.1853	0.057*
C12	0.6135 (4)	0.9195 (2)	0.0515 (3)	0.0472 (11)
H12A	0.5132	0.9307	0.0342	0.071*
H12B	0.6146	0.9076	−0.0048	0.071*
H12C	0.6774	0.9582	0.0817	0.071*
C13	0.2988 (3)	0.79106 (15)	0.2919 (2)	0.0196 (6)
H13	0.3342	0.7499	0.3244	0.023*
C14	0.2289 (3)	0.83811 (15)	0.3109 (2)	0.0231 (7)
H14	0.2059	0.8368	0.3584	0.028*
C15	0.2480 (3)	0.87125 (14)	0.1918 (2)	0.0177 (6)
C16	0.2259 (3)	0.91264 (15)	0.1117 (2)	0.0217 (7)
H16	0.2855	0.8924	0.0878	0.026*
C17	0.2765 (4)	0.98551 (15)	0.1391 (2)	0.0305 (8)
H17A	0.2169	1.0072	0.1604	0.046*
H17B	0.2651	1.0096	0.0848	0.046*
H17C	0.3797	0.9862	0.1896	0.046*
C18	0.0635 (4)	0.90979 (17)	0.0320 (2)	0.0328 (8)
H18A	0.0343	0.8631	0.0144	0.049*
H18B	0.0506	0.9345	−0.0222	0.049*
H18C	0.0024	0.93	0.0532	0.049*
C19	0.4603 (3)	0.64040 (14)	0.2861 (2)	0.0225 (7)
H19	0.5627	0.6452	0.3285	0.027*
C20	0.3729 (4)	0.59637 (16)	0.2946 (2)	0.0273 (7)
H20	0.4012	0.5648	0.3434	0.033*
C21	0.2391 (3)	0.65596 (14)	0.1655 (2)	0.0184 (6)
C22	0.1103 (3)	0.67838 (15)	0.0751 (2)	0.0223 (7)
H22	0.1356	0.7223	0.0585	0.027*
C23	0.0812 (4)	0.62825 (19)	−0.0015 (2)	0.0395 (9)
H23A	0.17	0.6229	−0.0041	0.059*
H23B	0.0013	0.6447	−0.0619	0.059*
H23C	0.0536	0.585	0.0123	0.059*
C24	−0.0242 (4)	0.68883 (19)	0.0820 (3)	0.0389 (9)
H24A	−0.054	0.646	0.0955	0.058*
H24B	−0.1044	0.7066	0.0227	0.058*
H24C	−0.0011	0.7206	0.1324	0.058*
Br2	0.96167 (4)	0.511235 (15)	0.20034 (3)	0.03505 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02145 (17)	0.02243 (16)	0.01668 (16)	−0.00041 (12)	0.00995 (13)	−0.00114 (12)
Cu1	0.01376 (19)	0.01431 (18)	0.01683 (19)	−0.00066 (14)	0.00923 (16)	−0.00082 (14)
N1	0.0161 (13)	0.0162 (12)	0.0198 (13)	0.0008 (10)	0.0100 (11)	0.0018 (11)
N2	0.0202 (14)	0.0239 (13)	0.0251 (14)	0.0077 (11)	0.0134 (12)	0.0037 (11)
N3	0.0166 (13)	0.0150 (11)	0.0185 (12)	−0.0001 (10)	0.0105 (11)	−0.0006 (10)
N4	0.0186 (13)	0.0196 (13)	0.0272 (14)	−0.0056 (11)	0.0126 (12)	−0.0028 (11)
N5	0.0147 (12)	0.0163 (12)	0.0173 (12)	−0.0005 (10)	0.0092 (11)	−0.0004 (10)
N6	0.0195 (14)	0.0232 (13)	0.0267 (14)	0.0048 (11)	0.0146 (12)	−0.0015 (12)
N7	0.0159 (13)	0.0158 (12)	0.0213 (13)	−0.0006 (10)	0.0099 (11)	−0.0008 (11)
N8	0.0226 (14)	0.0224 (13)	0.0306 (15)	−0.0056 (12)	0.0150 (13)	0.0033 (12)
C1	0.0190 (16)	0.0221 (15)	0.0180 (15)	−0.0021 (13)	0.0072 (13)	0.0001 (13)
C2	0.0159 (16)	0.0271 (16)	0.0214 (15)	0.0014 (13)	0.0059 (13)	0.0038 (14)
C3	0.0191 (16)	0.0183 (14)	0.0217 (15)	0.0013 (12)	0.0144 (13)	0.0052 (13)
C4	0.0203 (16)	0.0205 (15)	0.0203 (15)	0.0027 (13)	0.0125 (13)	−0.0015 (13)
C5	0.0328 (19)	0.0355 (19)	0.0232 (17)	0.0018 (16)	0.0170 (16)	0.0001 (15)
C6	0.036 (2)	0.0236 (16)	0.0334 (18)	−0.0031 (15)	0.0194 (17)	−0.0055 (15)
C7	0.0193 (16)	0.0206 (15)	0.0193 (15)	0.0007 (13)	0.0107 (13)	−0.0015 (13)
C8	0.0195 (16)	0.0241 (16)	0.0203 (16)	−0.0013 (13)	0.0071 (14)	−0.0078 (13)
C9	0.0152 (15)	0.0146 (14)	0.0216 (15)	−0.0002 (12)	0.0091 (13)	0.0000 (12)
C10	0.0230 (16)	0.0237 (15)	0.0236 (16)	−0.0039 (13)	0.0151 (14)	−0.0014 (13)
C11	0.038 (2)	0.048 (2)	0.041 (2)	0.0064 (18)	0.0295 (18)	0.0013 (18)
C12	0.052 (3)	0.066 (3)	0.030 (2)	0.022 (2)	0.027 (2)	0.018 (2)
C13	0.0194 (16)	0.0228 (15)	0.0194 (15)	0.0000 (13)	0.0121 (13)	0.0015 (13)
C14	0.0223 (16)	0.0285 (16)	0.0216 (15)	−0.0029 (14)	0.0136 (14)	−0.0033 (14)
C15	0.0129 (14)	0.0197 (15)	0.0184 (15)	−0.0025 (12)	0.0068 (13)	−0.0043 (12)
C16	0.0212 (16)	0.0219 (15)	0.0216 (15)	0.0047 (13)	0.0109 (14)	0.0013 (13)
C17	0.033 (2)	0.0225 (17)	0.0296 (18)	0.0012 (15)	0.0117 (16)	0.0066 (14)
C18	0.0311 (19)	0.0294 (17)	0.0248 (17)	0.0028 (15)	0.0056 (16)	0.0034 (15)
C19	0.0202 (16)	0.0223 (15)	0.0236 (15)	0.0034 (13)	0.0106 (14)	0.0060 (14)
C20	0.0262 (18)	0.0272 (17)	0.0256 (17)	0.0012 (14)	0.0115 (15)	0.0094 (15)
C21	0.0201 (16)	0.0158 (14)	0.0234 (15)	−0.0011 (12)	0.0141 (14)	−0.0008 (13)
C22	0.0182 (16)	0.0210 (15)	0.0267 (16)	−0.0027 (13)	0.0111 (14)	0.0018 (14)
C23	0.028 (2)	0.045 (2)	0.0281 (19)	−0.0014 (17)	0.0028 (16)	−0.0066 (17)
C24	0.0246 (19)	0.047 (2)	0.045 (2)	0.0101 (17)	0.0181 (18)	0.0131 (19)
Br2	0.0299 (2)	0.01770 (17)	0.0730 (3)	0.00417 (13)	0.0376 (2)	0.00779 (16)

Geometric parameters (Å, º) top

Br1—Cu1	2.6608 (6)	C7—H7	0.95
Cu1—N7	2.032 (2)	C8—H8	0.95
Cu1—N3	2.036 (2)	C9—C10	1.492 (4)
Cu1—N5	2.037 (2)	C10—C12	1.519 (5)
Cu1—N1	2.038 (2)	C10—C11	1.521 (4)
N1—C3	1.330 (4)	C10—H10	1
N1—C1	1.388 (4)	C11—H11A	0.98
N2—C3	1.350 (4)	C11—H11B	0.98
N2—C2	1.371 (4)	C11—H11C	0.98
N2—H2A	0.88	C12—H12A	0.98
N3—C9	1.332 (4)	C12—H12B	0.98
N3—C7	1.384 (3)	C12—H12C	0.98
N4—C9	1.360 (4)	C13—C14	1.340 (4)
N4—C8	1.364 (4)	C13—H13	0.95
N4—H4A	0.88	C14—H14	0.95
N5—C15	1.324 (4)	C15—C16	1.489 (4)
N5—C13	1.392 (4)	C16—C17	1.539 (4)
N6—C15	1.354 (4)	C16—C18	1.544 (4)
N6—C14	1.369 (4)	C16—H16	1
N6—H6D	0.88	C17—H17A	0.98
N7—C21	1.330 (4)	C17—H17B	0.98
N7—C19	1.394 (4)	C17—H17C	0.98
N8—C21	1.350 (4)	C18—H18A	0.98
N8—C20	1.375 (4)	C18—H18B	0.98
N8—H8A	0.88	C18—H18C	0.98
C1—C2	1.350 (4)	C19—C20	1.346 (4)
C1—H1	0.95	C19—H19	0.95
C2—H2	0.95	C20—H20	0.95
C3—C4	1.490 (4)	C21—C22	1.489 (4)
C4—C5	1.529 (4)	C22—C24	1.520 (4)
C4—C6	1.536 (4)	C22—C23	1.528 (5)
C4—H4	1	C22—H22	1
C5—H5A	0.98	C23—H23A	0.98
C5—H5B	0.98	C23—H23B	0.98
C5—H5C	0.98	C23—H23C	0.98
C6—H6A	0.98	C24—H24A	0.98
C6—H6B	0.98	C24—H24B	0.98
C6—H6C	0.98	C24—H24C	0.98
C7—C8	1.342 (4)

N7—Cu1—N3	155.70 (9)	C9—C10—C11	112.2 (3)
N7—Cu1—N5	87.00 (9)	C12—C10—C11	110.3 (3)
N3—Cu1—N5	87.54 (9)	C9—C10—H10	108.1
N7—Cu1—N1	87.23 (9)	C12—C10—H10	108.1
N3—Cu1—N1	87.47 (9)	C11—C10—H10	108.1
N5—Cu1—N1	154.22 (9)	C10—C11—H11A	109.5
N7—Cu1—Br1	103.58 (7)	C10—C11—H11B	109.5
N3—Cu1—Br1	100.72 (7)	H11A—C11—H11B	109.5
N5—Cu1—Br1	102.30 (7)	C10—C11—H11C	109.5
N1—Cu1—Br1	103.47 (7)	H11A—C11—H11C	109.5
C3—N1—C1	106.4 (2)	H11B—C11—H11C	109.5
C3—N1—Cu1	130.2 (2)	C10—C12—H12A	109.5
C1—N1—Cu1	122.86 (19)	C10—C12—H12B	109.5
C3—N2—C2	109.2 (2)	H12A—C12—H12B	109.5
C3—N2—H2A	125.4	C10—C12—H12C	109.5
C2—N2—H2A	125.4	H12A—C12—H12C	109.5
C9—N3—C7	106.4 (2)	H12B—C12—H12C	109.5
C9—N3—Cu1	130.20 (19)	C14—C13—N5	109.6 (3)
C7—N3—Cu1	121.06 (18)	C14—C13—H13	125.2
C9—N4—C8	108.7 (2)	N5—C13—H13	125.2
C9—N4—H4A	125.7	C13—C14—N6	106.0 (3)
C8—N4—H4A	125.7	C13—C14—H14	127
C15—N5—C13	106.4 (2)	N6—C14—H14	127
C15—N5—Cu1	129.80 (19)	N5—C15—N6	109.2 (3)
C13—N5—Cu1	121.74 (19)	N5—C15—C16	127.1 (3)
C15—N6—C14	108.9 (2)	N6—C15—C16	123.7 (3)
C15—N6—H6D	125.6	C15—C16—C17	113.0 (3)
C14—N6—H6D	125.6	C15—C16—C18	109.7 (3)
C21—N7—C19	106.8 (2)	C17—C16—C18	110.8 (3)
C21—N7—Cu1	129.27 (19)	C15—C16—H16	107.7
C19—N7—Cu1	120.74 (19)	C17—C16—H16	107.7
C21—N8—C20	108.9 (2)	C18—C16—H16	107.7
C21—N8—H8A	125.5	C16—C17—H17A	109.5
C20—N8—H8A	125.5	C16—C17—H17B	109.5
C2—C1—N1	109.7 (3)	H17A—C17—H17B	109.5
C2—C1—H1	125.2	C16—C17—H17C	109.5
N1—C1—H1	125.2	H17A—C17—H17C	109.5
C1—C2—N2	105.5 (3)	H17B—C17—H17C	109.5
C1—C2—H2	127.3	C16—C18—H18A	109.5
N2—C2—H2	127.3	C16—C18—H18B	109.5
N1—C3—N2	109.2 (3)	H18A—C18—H18B	109.5
N1—C3—C4	126.9 (3)	C16—C18—H18C	109.5
N2—C3—C4	124.0 (3)	H18A—C18—H18C	109.5
C3—C4—C5	110.9 (3)	H18B—C18—H18C	109.5
C3—C4—C6	112.4 (3)	C20—C19—N7	109.0 (3)
C5—C4—C6	110.3 (3)	C20—C19—H19	125.5
C3—C4—H4	107.7	N7—C19—H19	125.5
C5—C4—H4	107.7	C19—C20—N8	106.2 (3)
C6—C4—H4	107.7	C19—C20—H20	126.9
C4—C5—H5A	109.5	N8—C20—H20	126.9
C4—C5—H5B	109.5	N7—C21—N8	109.1 (3)
H5A—C5—H5B	109.5	N7—C21—C22	126.9 (3)
C4—C5—H5C	109.5	N8—C21—C22	123.9 (3)
H5A—C5—H5C	109.5	C21—C22—C24	111.9 (3)
H5B—C5—H5C	109.5	C21—C22—C23	109.4 (3)
C4—C6—H6A	109.5	C24—C22—C23	111.7 (3)
C4—C6—H6B	109.5	C21—C22—H22	107.9
H6A—C6—H6B	109.5	C24—C22—H22	107.9
C4—C6—H6C	109.5	C23—C22—H22	107.9
H6A—C6—H6C	109.5	C22—C23—H23A	109.5
H6B—C6—H6C	109.5	C22—C23—H23B	109.5
C8—C7—N3	109.7 (3)	H23A—C23—H23B	109.5
C8—C7—H7	125.1	C22—C23—H23C	109.5
N3—C7—H7	125.1	H23A—C23—H23C	109.5
C7—C8—N4	106.2 (3)	H23B—C23—H23C	109.5
C7—C8—H8	126.9	C22—C24—H24A	109.5
N4—C8—H8	126.9	C22—C24—H24B	109.5
N3—C9—N4	108.9 (2)	H24A—C24—H24B	109.5
N3—C9—C10	127.8 (3)	C22—C24—H24C	109.5
N4—C9—C10	123.3 (3)	H24A—C24—H24C	109.5
C9—C10—C12	110.0 (3)	H24B—C24—H24C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Br2	0.88	2.48	3.358 (2)	175
N4—H4A···Br2ⁱ	0.88	2.48	3.342 (2)	167
N6—H6D···Br2ⁱⁱ	0.88	2.53	3.351 (2)	155
N8—H8A···Br2ⁱⁱⁱ	0.88	2.49	3.362 (2)	169

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

Experimental details

Crystal data
Chemical formula	[CuBr(C₆H₁₀N₂)₄]Br
M_r	664
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	10.7094 (7), 19.9917 (6), 16.7885 (19)
β (°)	121.552 (7)
V (Å³)	3063.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.35
Crystal size (mm)	0.41 × 0.25 × 0.23

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire2
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.628, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	11133, 5710, 4597
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.092, 1.05
No. of reflections	5710
No. of parameters	324
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.86, −1.04

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Br2	0.88	2.48	3.358 (2)	175.1
N4—H4A···Br2ⁱ	0.88	2.48	3.342 (2)	167.1
N6—H6D···Br2ⁱⁱ	0.88	2.53	3.351 (2)	154.8
N8—H8A···Br2ⁱⁱⁱ	0.88	2.49	3.362 (2)	169.4

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

Acknowledgements

SA thanks the Polish Ministry of Science and Higher Education for financial support (decision Nr 155/03/E-359/M/2011).

References

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