Bis[bis­(1H-benzimidazol-2-ylmeth­yl)amine]copper(II) dichloride methanol disolvate dihydrate

Xia, X.; Zhang, Y.; Qu, Y.; Chen, X.; Liu, T.

doi:10.1107/S1600536807065816

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page m190

https://doi.org/10.1107/S1600536807065816

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Bis[bis(1H-benzimidazol-2-ylmethyl)amine]copper(II) dichloride methanol disolvate dihydrate

Xian-you Xia,^a Yong Zhang,^a ^* Yuan Qu,^a Xue-mei Chen ^a and Ting Liu ^a

^aSchool of Chemical and Materials Engineering, Huangshi Institute of Technology, Huangshi 435003, People's Republic of China
^*Correspondence e-mail: zy0340907@yahoo.com.cn

(Received 16 November 2007; accepted 5 December 2007; online 18 December 2007)

In the title compound, [Cu(C₁₆H₁₄N₅)₂]Cl₂·2CH₄O·2H₂O, the cationic metal complex resides on a crystallographic centre of inversion, with the Cu²⁺ bonded to two bis(1H-benzimidazol-2-ylmethyl)amines (IDB). The coordination geometry of the Cu²⁺ ion is distorted octahedral with an N₆ ligand set. A three-dimensional framework structure is formed by means of hydrogen bonds and π–π interactions formed between imidazole and phenyl rings, and between phenyl and phenyl rings, with centroid-to-centroid distances of 3.690 (2)–3.977 (2) Å and interplanar spacings of 3.445 (2)–3.502 (2) Å.

Related literature

For related literature, see: Adams et al. (1990 ); Qin et al. (2005 ); Santoro et al. (2000 ); Suresh et al. (2006 ); Yan et al. (2004 ); Yu et al. (2006 ). For the treatment of disordered solvent, see: Spek (2003 ).

Experimental

Crystal data

[Cu(C₁₆H₁₄N₅)₂]Cl₂·2CH₄O·2H₂O
M_r = 725.13
Triclinic, $[P \overline 1]$
a = 9.653 (3) Å
b = 9.921 (3) Å
c = 10.316 (3) Å
α = 82.095 (5)°
β = 88.441 (5)°
γ = 87.073 (5)°
V = 977.1 (5) Å³
Z = 1
Mo Kα radiation
μ = 0.74 mm⁻¹
T = 292 (2) K
0.23 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
9121 measured reflections
3799 independent reflections
2937 reflections with I > 2σ(I)
R_int = 0.099

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.123
S = 0.97
3799 reflections
229 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O1	0.860 (10)	2.027 (15)	2.839 (4)	157 (3)
O1—H1B⋯Cl1	0.81 (4)	2.59 (4)	3.206 (4)	134 (5)
N1—H1C⋯Cl1ⁱ	0.855 (10)	2.455 (12)	3.296 (3)	168 (3)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: Bruker SMART CCD (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807065816/gg2050sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807065816/gg2050Isup2.hkl

checkCIF report

Comment top

Imidazole (Im) and benzimidazole (Bzim) are common species having biological and biochemical structure and function (Santoro et al., 2000). Several compounds containing more than one benzimidazole moiety have been reported recently, e.g. Yan et al. (2004), Qin et al. (2005), and Yu et al. (2006). The title compound, (I), was prepared in a series of syntheses to produce new benzimidazole derivatives, and we report the crystal stucture herein.

The main geometric parameters of (I) are listed in Table 1, and the molecule structure is illustrated in Fig. 1. In (I), the Cu atom displays a distorted octahedral coordination geometry provided by two tridentate IDB ligands: one amine N atom and one benzimidazolyl N atom of each ligand make up the equatorial plane and another benzimidazolyl N atom of each ligand occupies the axial position. As shown in Table 2 and Fig. 2, the molecules are stablized by intermolecular Cl···H—N, Cl···H—O and O···H—N hydrogen bonds and π···π stacking, leading to the formation of a three dimension network.

Related literature top

For related literature, see: Adams et al. (1990); Qin et al. (2005); Santoro et al. (2000); Spek (2003); Suresh et al. (2006); Yan et al. (2004); Yu et al. (2006); Sheldrick (2003).

Experimental top

All reagents and solvents were used as obtained without further purification. Bis(benzimidazol-2-yl-methyl)amine (IDB) was prepared according to the method described by Adams et al. (1990). Compound (I) was synthesized by reaction of IDB (0.54 g, 2 mmol) and copper(II) chloride dihydrate (0.17 g, 1 mmol) in methanol (40 ml) at 333 K for 8 h. The resulting solution was filtered and purple crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of the filtrate at room temperature after one week (yield 55%).

Structure description top

For related literature, see: Adams et al. (1990); Qin et al. (2005); Santoro et al. (2000); Spek (2003); Suresh et al. (2006); Yan et al. (2004); Yu et al. (2006); Sheldrick (2003).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top

	Fig. 1. Molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 2. Plot of the crystal packing showing the linkage of the molecules by H-bonding and π–π interactions shown as dashed lines.

Bis[bis(1H-benzimidazol-2-ylmethyl)amine]copper(II) dichloride methanol disolvate dihydrate top

Crystal data top

[Cu(C₁₆H₁₄N₅)₂]Cl₂·2CH₄O·2H₂O	Z = 1
M_r = 725.13	F(000) = 375
Triclinic, P1	D_x = 1.232 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.653 (3) Å	Cell parameters from 3239 reflections
b = 9.921 (3) Å	θ = 1.6–25.5°
c = 10.316 (3) Å	µ = 0.74 mm⁻¹
α = 82.095 (5)°	T = 292 K
β = 88.441 (5)°	Block, purple
γ = 87.073 (5)°	0.23 × 0.22 × 0.20 mm
V = 977.1 (5) Å³

Data collection top

CCD area-detector diffractometer	2937 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.099
Graphite monochromator	θ_max = 26.0°, θ_min = 2.0°
φ and ω scans	h = −11→11
9121 measured reflections	k = −12→12
3799 independent reflections	l = −12→12

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ²(F_o²) + (0.0459P)²] where P = (F_o² + 2F_c²)/3
3799 reflections	(Δ/σ)_max < 0.001
229 parameters	Δρ_max = 0.60 e Å⁻³
6 restraints	Δρ_min = −0.60 e Å⁻³

Crystal data top

[Cu(C₁₆H₁₄N₅)₂]Cl₂·2CH₄O·2H₂O	γ = 87.073 (5)°
M_r = 725.13	V = 977.1 (5) Å³
Triclinic, P1	Z = 1
a = 9.653 (3) Å	Mo Kα radiation
b = 9.921 (3) Å	µ = 0.74 mm⁻¹
c = 10.316 (3) Å	T = 292 K
α = 82.095 (5)°	0.23 × 0.22 × 0.20 mm
β = 88.441 (5)°

Data collection top

CCD area-detector diffractometer	2937 reflections with I > 2σ(I)
9121 measured reflections	R_int = 0.099
3799 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	6 restraints
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	Δρ_max = 0.60 e Å⁻³
3799 reflections	Δρ_min = −0.60 e Å⁻³
229 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
Cu1	0.5000	0.5000	1.0000	0.02773 (17)
N1	0.4996 (3)	0.5259 (2)	0.7434 (2)	0.0378 (6)
H1C	0.530 (3)	0.597 (2)	0.696 (2)	0.045*
N2	0.1441 (3)	0.4115 (3)	0.8191 (3)	0.0434 (7)
H2	0.106 (3)	0.406 (4)	0.746 (2)	0.052*
N3	0.3091 (2)	0.4492 (2)	0.9528 (2)	0.0337 (6)
N4	0.6536 (3)	0.1732 (3)	0.8228 (3)	0.0384 (6)
H4	0.678 (3)	0.154 (3)	0.7466 (17)	0.046*
N5	0.5738 (2)	0.3203 (2)	0.9531 (2)	0.0308 (5)
C1	0.0971 (3)	0.3621 (3)	0.9427 (3)	0.0410 (8)
C2	−0.0207 (4)	0.2958 (4)	0.9870 (4)	0.0536 (10)
H2A	−0.0891	0.2804	0.9297	0.064*
C3	−0.0330 (4)	0.2534 (4)	1.1187 (4)	0.0652 (11)
H3	−0.1117	0.2092	1.1520	0.078*
C4	0.0712 (4)	0.2759 (4)	1.2042 (4)	0.0604 (10)
H4A	0.0607	0.2452	1.2930	0.072*
C5	0.1892 (4)	0.3426 (4)	1.1598 (3)	0.0467 (9)
H5	0.2577	0.3575	1.2172	0.056*
C6	0.2023 (3)	0.3866 (3)	1.0261 (3)	0.0351 (7)
C7	0.2717 (3)	0.4620 (3)	0.8288 (3)	0.0362 (7)
C8	0.3527 (4)	0.5231 (3)	0.7149 (3)	0.0467 (9)
H8A	0.3423	0.4713	0.6428	0.056*
H8B	0.3164	0.6154	0.6878	0.056*
C9	0.5817 (4)	0.4056 (3)	0.7148 (3)	0.0472 (9)
H9A	0.6722	0.4331	0.6808	0.057*
H9B	0.5365	0.3659	0.6472	0.057*
C10	0.6004 (3)	0.3008 (3)	0.8311 (3)	0.0332 (7)
C11	0.6591 (3)	0.1038 (3)	0.9456 (3)	0.0358 (7)
C12	0.7028 (4)	−0.0289 (3)	0.9947 (4)	0.0478 (9)
H12	0.7384	−0.0894	0.9394	0.057*
C13	0.6915 (4)	−0.0673 (3)	1.1271 (4)	0.0512 (9)
H13	0.7205	−0.1552	1.1623	0.061*
C14	0.6370 (4)	0.0231 (3)	1.2104 (3)	0.0465 (8)
H14	0.6298	−0.0062	1.2998	0.056*
C15	0.5939 (3)	0.1543 (3)	1.1627 (3)	0.0392 (7)
H15	0.5565	0.2135	1.2183	0.047*
C16	0.6075 (3)	0.1957 (3)	1.0300 (3)	0.0307 (6)
Cl1	0.37341 (12)	0.23380 (10)	0.47316 (9)	0.0656 (3)
O1	0.6586 (3)	0.0805 (3)	0.5743 (3)	0.0720 (9)
H1B	0.624 (5)	0.138 (3)	0.520 (4)	0.108*
H1A	0.628 (5)	0.009 (3)	0.588 (5)	0.108*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0332 (3)	0.0220 (3)	0.0305 (3)	−0.00342 (19)	−0.0075 (2)	−0.01034 (19)
N1	0.0506 (17)	0.0288 (13)	0.0344 (14)	−0.0086 (12)	−0.0034 (12)	−0.0028 (11)
N2	0.0460 (16)	0.0366 (14)	0.0493 (18)	−0.0054 (12)	−0.0220 (14)	−0.0071 (13)
N3	0.0357 (14)	0.0305 (13)	0.0373 (14)	−0.0051 (10)	−0.0075 (11)	−0.0104 (11)
N4	0.0492 (16)	0.0336 (14)	0.0354 (15)	−0.0016 (12)	0.0020 (13)	−0.0164 (12)
N5	0.0380 (14)	0.0249 (12)	0.0316 (13)	−0.0010 (10)	−0.0036 (11)	−0.0108 (10)
C1	0.0386 (18)	0.0319 (16)	0.054 (2)	0.0019 (13)	−0.0136 (16)	−0.0111 (14)
C2	0.039 (2)	0.054 (2)	0.070 (3)	−0.0086 (16)	−0.0110 (18)	−0.0128 (19)
C3	0.041 (2)	0.072 (3)	0.085 (3)	−0.0179 (19)	0.008 (2)	−0.015 (2)
C4	0.057 (2)	0.074 (3)	0.052 (2)	−0.015 (2)	0.0098 (18)	−0.013 (2)
C5	0.0430 (19)	0.055 (2)	0.046 (2)	−0.0066 (16)	−0.0051 (16)	−0.0175 (17)
C6	0.0345 (16)	0.0269 (14)	0.0467 (19)	0.0031 (12)	−0.0068 (14)	−0.0152 (13)
C7	0.0421 (18)	0.0271 (14)	0.0407 (17)	−0.0034 (13)	−0.0115 (14)	−0.0070 (13)
C8	0.057 (2)	0.0439 (19)	0.0391 (18)	−0.0100 (16)	−0.0185 (17)	0.0000 (15)
C9	0.069 (2)	0.0408 (18)	0.0341 (17)	−0.0025 (17)	0.0002 (16)	−0.0120 (14)
C10	0.0404 (17)	0.0268 (15)	0.0350 (16)	−0.0049 (12)	−0.0030 (13)	−0.0116 (12)
C11	0.0361 (17)	0.0305 (15)	0.0433 (18)	−0.0044 (13)	−0.0023 (14)	−0.0124 (14)
C12	0.054 (2)	0.0313 (17)	0.059 (2)	0.0059 (15)	−0.0006 (17)	−0.0131 (16)
C13	0.057 (2)	0.0276 (17)	0.067 (2)	0.0062 (15)	−0.0059 (19)	−0.0015 (16)
C14	0.052 (2)	0.0384 (18)	0.047 (2)	−0.0027 (15)	−0.0065 (17)	0.0012 (15)
C15	0.0443 (18)	0.0322 (16)	0.0427 (18)	−0.0009 (13)	−0.0058 (15)	−0.0106 (14)
C16	0.0293 (15)	0.0256 (14)	0.0387 (16)	−0.0028 (11)	−0.0048 (13)	−0.0082 (12)
Cl1	0.0962 (8)	0.0549 (6)	0.0461 (5)	−0.0196 (5)	−0.0092 (5)	−0.0009 (4)
O1	0.084 (2)	0.076 (2)	0.064 (2)	−0.0184 (18)	0.0032 (16)	−0.0355 (17)

Geometric parameters (Å, º) top

Cu1—N1	2.624 (3)	C3—H3	0.9300
Cu1—N3ⁱ	2.024 (2)	C4—C5	1.382 (5)
Cu1—N3	2.024 (2)	C4—H4A	0.9300
Cu1—N5ⁱ	2.002 (2)	C5—C6	1.392 (5)
Cu1—N5	2.002 (2)	C5—H5	0.9300
N1—C9	1.459 (4)	C7—C8	1.470 (5)
N1—C8	1.459 (4)	C8—H8A	0.9700
N1—H1C	0.855 (10)	C8—H8B	0.9700
N2—C7	1.365 (4)	C9—C10	1.484 (5)
N2—C1	1.375 (4)	C9—H9A	0.9700
N2—H2	0.858 (10)	C9—H9B	0.9700
N3—C7	1.326 (4)	C11—C12	1.393 (4)
N3—C6	1.384 (4)	C11—C16	1.408 (4)
N4—C10	1.354 (4)	C12—C13	1.369 (5)
N4—C11	1.357 (4)	C12—H12	0.9300
N4—H4	0.860 (10)	C13—C14	1.400 (5)
N5—C10	1.316 (4)	C13—H13	0.9300
N5—C16	1.402 (4)	C14—C15	1.374 (4)
C1—C2	1.378 (5)	C14—H14	0.9300
C1—C6	1.400 (4)	C15—C16	1.379 (4)
C2—C3	1.370 (6)	C15—H15	0.9300
C2—H2A	0.9300	O1—H1A	0.778 (17)
C3—C4	1.401 (5)

N5ⁱ—Cu1—N5	180.00 (13)	C6—C5—H5	121.1
N5ⁱ—Cu1—N3ⁱ	88.03 (9)	N3—C6—C5	131.1 (3)
N5—Cu1—N3ⁱ	91.97 (9)	N3—C6—C1	109.4 (3)
N5ⁱ—Cu1—N3	91.97 (9)	C5—C6—C1	119.4 (3)
N5—Cu1—N3	88.03 (9)	N3—C7—N2	110.7 (3)
N3ⁱ—Cu1—N3	180.00 (12)	N3—C7—C8	126.1 (3)
N5ⁱ—Cu1—N1	105.57 (9)	N2—C7—C8	123.2 (3)
N5—Cu1—N1	74.43 (9)	N1—C8—C7	112.1 (3)
N3ⁱ—Cu1—N1	105.76 (9)	N1—C8—H8A	109.2
N3—Cu1—N1	74.24 (9)	C7—C8—H8A	109.2
C9—N1—C8	114.0 (2)	N1—C8—H8B	109.2
C9—N1—Cu1	102.82 (18)	C7—C8—H8B	109.2
C8—N1—Cu1	102.97 (19)	H8A—C8—H8B	107.9
C9—N1—H1C	109 (2)	N1—C9—C10	113.0 (3)
C8—N1—H1C	106 (2)	N1—C9—H9A	109.0
Cu1—N1—H1C	122 (2)	C10—C9—H9A	109.0
C7—N2—C1	108.6 (2)	N1—C9—H9B	109.0
C7—N2—H2	124 (2)	C10—C9—H9B	109.0
C1—N2—H2	128 (2)	H9A—C9—H9B	107.8
C7—N3—C6	106.4 (2)	N5—C10—N4	112.0 (3)
C7—N3—Cu1	120.7 (2)	N5—C10—C9	125.3 (3)
C6—N3—Cu1	132.5 (2)	N4—C10—C9	122.7 (3)
C10—N4—C11	108.2 (2)	N4—C11—C12	133.0 (3)
C10—N4—H4	118 (2)	N4—C11—C16	106.0 (3)
C11—N4—H4	134 (2)	C12—C11—C16	120.9 (3)
C10—N5—C16	105.9 (2)	C13—C12—C11	117.7 (3)
C10—N5—Cu1	122.1 (2)	C13—C12—H12	121.2
C16—N5—Cu1	131.95 (19)	C11—C12—H12	121.2
N2—C1—C2	132.2 (3)	C12—C13—C14	121.3 (3)
N2—C1—C6	104.9 (3)	C12—C13—H13	119.3
C2—C1—C6	122.8 (3)	C14—C13—H13	119.3
C3—C2—C1	117.4 (3)	C15—C14—C13	121.3 (3)
C3—C2—H2A	121.3	C15—C14—H14	119.4
C1—C2—H2A	121.3	C13—C14—H14	119.4
C2—C3—C4	120.9 (4)	C14—C15—C16	118.2 (3)
C2—C3—H3	119.5	C14—C15—H15	120.9
C4—C3—H3	119.5	C16—C15—H15	120.9
C5—C4—C3	121.7 (4)	C15—C16—N5	131.6 (3)
C5—C4—H4A	119.1	C15—C16—C11	120.6 (3)
C3—C4—H4A	119.1	N5—C16—C11	107.8 (3)
C4—C5—C6	117.8 (3)	H1B—O1—H1A	120 (3)
C4—C5—H5	121.1

N5ⁱ—Cu1—N1—C9	167.82 (19)	C6—N3—C7—N2	0.6 (3)
N5—Cu1—N1—C9	−12.18 (19)	Cu1—N3—C7—N2	174.94 (19)
N3ⁱ—Cu1—N1—C9	75.4 (2)	C6—N3—C7—C8	179.9 (3)
N3—Cu1—N1—C9	−104.6 (2)	Cu1—N3—C7—C8	−5.8 (4)
N5ⁱ—Cu1—N1—C8	−73.47 (19)	C1—N2—C7—N3	−0.7 (4)
N5—Cu1—N1—C8	106.53 (19)	C1—N2—C7—C8	179.9 (3)
N3ⁱ—Cu1—N1—C8	−165.85 (18)	C9—N1—C8—C7	90.9 (3)
N3—Cu1—N1—C8	14.15 (18)	Cu1—N1—C8—C7	−19.7 (3)
N5ⁱ—Cu1—N3—C7	100.4 (2)	N3—C7—C8—N1	20.5 (5)
N5—Cu1—N3—C7	−79.6 (2)	N2—C7—C8—N1	−160.3 (3)
N1—Cu1—N3—C7	−5.3 (2)	C8—N1—C9—C10	−95.4 (3)
N5ⁱ—Cu1—N3—C6	−87.1 (3)	Cu1—N1—C9—C10	15.3 (3)
N5—Cu1—N3—C6	92.9 (3)	C16—N5—C10—N4	−2.0 (3)
N1—Cu1—N3—C6	167.3 (3)	Cu1—N5—C10—N4	178.00 (18)
N3ⁱ—Cu1—N5—C10	−99.2 (2)	C16—N5—C10—C9	−179.4 (3)
N3—Cu1—N5—C10	80.8 (2)	Cu1—N5—C10—C9	0.7 (4)
N1—Cu1—N5—C10	6.6 (2)	C11—N4—C10—N5	1.6 (3)
N3ⁱ—Cu1—N5—C16	80.8 (2)	C11—N4—C10—C9	179.0 (3)
N3—Cu1—N5—C16	−99.2 (2)	N1—C9—C10—N5	−13.7 (4)
N1—Cu1—N5—C16	−173.3 (3)	N1—C9—C10—N4	169.2 (3)
C7—N2—C1—C2	−176.6 (4)	C10—N4—C11—C12	179.4 (3)
C7—N2—C1—C6	0.5 (3)	C10—N4—C11—C16	−0.4 (3)
N2—C1—C2—C3	176.8 (4)	N4—C11—C12—C13	−178.7 (3)
C6—C1—C2—C3	0.2 (5)	C16—C11—C12—C13	1.1 (5)
C1—C2—C3—C4	−0.6 (6)	C11—C12—C13—C14	0.5 (5)
C2—C3—C4—C5	0.7 (7)	C12—C13—C14—C15	−0.6 (5)
C3—C4—C5—C6	−0.4 (6)	C13—C14—C15—C16	−0.9 (5)
C7—N3—C6—C5	176.4 (3)	C14—C15—C16—N5	180.0 (3)
Cu1—N3—C6—C5	3.0 (5)	C14—C15—C16—C11	2.5 (4)
C7—N3—C6—C1	−0.3 (3)	C10—N5—C16—C15	−176.0 (3)
Cu1—N3—C6—C1	−173.7 (2)	Cu1—N5—C16—C15	3.9 (5)
C4—C5—C6—N3	−176.5 (3)	C10—N5—C16—C11	1.7 (3)
C4—C5—C6—C1	−0.1 (5)	Cu1—N5—C16—C11	−178.31 (18)
N2—C1—C6—N3	−0.1 (3)	N4—C11—C16—C15	177.2 (3)
C2—C1—C6—N3	177.3 (3)	C12—C11—C16—C15	−2.6 (4)
N2—C1—C6—C5	−177.2 (3)	N4—C11—C16—N5	−0.8 (3)
C2—C1—C6—C5	0.2 (5)	C12—C11—C16—N5	179.3 (3)

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1	0.86 (1)	2.03 (2)	2.839 (4)	157 (3)
O1—H1B···Cl1	0.81 (4)	2.59 (4)	3.206 (4)	134 (5)
N1—H1C···Cl1ⁱⁱ	0.86 (1)	2.46 (1)	3.296 (3)	168 (3)

Symmetry code: (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₆H₁₄N₅)₂]Cl₂·2CH₄O·2H₂O
M_r	725.13
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	9.653 (3), 9.921 (3), 10.316 (3)
α, β, γ (°)	82.095 (5), 88.441 (5), 87.073 (5)
V (Å³)	977.1 (5)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.74
Crystal size (mm)	0.23 × 0.22 × 0.20

Data collection
Diffractometer	CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9121, 3799, 2937
R_int	0.099
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.123, 0.97
No. of reflections	3799
No. of parameters	229
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.60

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1	0.860 (10)	2.027 (15)	2.839 (4)	157 (3)
O1—H1B···Cl1	0.81 (4)	2.59 (4)	3.206 (4)	134 (5)
N1—H1C···Cl1ⁱ	0.855 (10)	2.455 (12)	3.296 (3)	168 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

References

Adams, H., Bailey, N. A., Carane, J. D. & Fenton, D. E. (1990). J. Chem. Soc. Dalton Trans. pp. 1727–1735. CSD CrossRef Web of Science Google Scholar
Bruker (1997). SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2001). SAINT-Plus (Version 6.45) and SMART (Version 5.628). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Qin, S.-D., Feng, S.-S., Zhang, H.-M., Yang, P. & Zhu, M.-L. (2005). Acta Cryst. E61, o1574–o1576. Web of Science CSD CrossRef IUCr Journals Google Scholar
Santoro, S. W., Joyce, G. F., Sakthivel, K., Gramatikova, S. & Barbas, C. F. (2000). J. Am. Chem. Soc. 122, 2433–2439. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Suresh, J., Alex Raja, V. P., Perumal, S. & Natarajan, S. (2006). Acta Cryst. E62, o3307–o3309. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yan, X.-X., Lu, L.-P. & Zhu, M.-L. (2004). Acta Cryst. C60, m221–m223. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Yu, B.-B., Meng, X.-G. & Liao, Z.-R. (2006). Acta Cryst. E62, m1519–m1521. Web of Science CSD CrossRef IUCr Journals Google Scholar

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

Bis[bis­­(1H-benzimidazol-2-ylmeth­yl)amine]copper(II) dichloride methanol disolvate dihydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

metal-organic compounds

Bis[bis(1H-benzimidazol-2-ylmethyl)amine]copper(II) dichloride methanol disolvate dihydrate