Acetato-chlorido[2,2'-(ethane-1,2-di-yl)di-1H-benzimidazole]-copper(II) monohydrate.

In the title complex, [Cu(CH(3)COO)Cl(C(16)H(14)N(4))]·H(2)O, the Cu(II) ion is five-coordinated by two N atoms from a 2,2'-(ethane-1,2-di-yl)di-1H-benzimidazole ligand, two O atoms from a chelating acetate ligand and one terminal monodentate Cl atom in a distorted square-pyramidal geometry. In the crystal, adjacent mol-ecules are linked through O-H⋯Cl, N-H⋯Cl, N-H⋯O and O-H⋯O hydrogen bonds into a three-dimensional network.

Related literature

1,2-Bis(2,2′-1H-benzimidazol)ethane (bbe) has been extensively used in the construction of complexes since it has multiple nitro­gen donors which show strong coordination ability, see: Yang et al. (2010 ▶); van Albada et al. (2000 ▶). For the potential applications of copper complexes, see: Mirica et al. (2004 ▶); Zhang et al. (2008 ▶).

Experimental

Crystal data

[Cu(C2H3O2)Cl(C16H14N4)]·H2O

M = 438.36

Monoclinic,

a = 14.796 (3) Å

b = 8.5844 (17) Å

c = 15.162 (3) Å

β = 108.04 (3)°

V = 1831.2 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.37 mm−1

T = 293 K

0.22 × 0.20 × 0.19 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006 ▶) T min = 0.753, T max = 0.781

12276 measured reflections

3573 independent reflections

3135 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.101

S = 1.07

3573 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2006 ▶); 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 datablocks global, I. DOI: 10.1107/S160053681003326X/br2145sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003326X/br2145Isup2.hkl

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

[Cu(C2H3O2)Cl(C16H14N4)]·H2O	F(000) = 900
Mr = 438.36	Dx = 1.590 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4685 reflections
a = 14.796 (3) Å	θ = 2.3–27.9°
b = 8.5844 (17) Å	µ = 1.37 mm−1
c = 15.162 (3) Å	T = 293 K
β = 108.04 (3)°	Prism, green
V = 1831.2 (6) Å3	0.22 × 0.20 × 0.19 mm
Z = 4

Rigaku Saturn diffractometer	3573 independent reflections
Radiation source: fine-focus sealed tube	3135 reflections with I > 2σ(I)
graphite	Rint = 0.029
Detector resolution: 28.5714 pixels mm-1	θmax = 26.0°, θmin = 2.8°
ω scans	h = −18→18
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006)	k = −10→10
Tmin = 0.753, Tmax = 0.781	l = −18→15
12276 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0516P)2 + 0.5788P] where P = (Fo2 + 2Fc2)/3
3573 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

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
Cu1	0.23644 (2)	0.50951 (3)	0.26280 (2)	0.03006 (13)
N1	0.19690 (16)	0.3120 (2)	0.19598 (15)	0.0313 (5)
N2	0.19221 (17)	0.0579 (3)	0.17476 (17)	0.0390 (6)
H2A	0.2008	−0.0398	0.1871	0.047*
N3	0.37363 (16)	0.4577 (3)	0.32508 (16)	0.0338 (5)
N4	0.51000 (17)	0.3474 (3)	0.40310 (16)	0.0398 (6)
H4A	0.5499	0.2766	0.4306	0.048*
O1	0.22960 (14)	0.6870 (2)	0.35141 (14)	0.0436 (5)
O2	0.10300 (14)	0.5737 (2)	0.26343 (13)	0.0402 (5)
O3	0.34911 (15)	0.6401 (2)	0.00045 (14)	0.0475 (5)
H1W	0.3208	0.6478	0.0390	0.057*
H2W	0.3163	0.6933	−0.0425	0.057*
Cl1	0.23462 (6)	0.70125 (8)	0.13960 (5)	0.0456 (2)
C1	0.15038 (18)	0.2829 (3)	0.10261 (18)	0.0297 (6)
C2	0.1067 (2)	0.3812 (3)	0.02902 (19)	0.0371 (7)
H2B	0.1059	0.4885	0.0370	0.044*
C3	0.0645 (2)	0.3135 (4)	−0.0563 (2)	0.0472 (8)
H3A	0.0336	0.3767	−0.1064	0.057*
C4	0.0669 (2)	0.1537 (4)	−0.0695 (2)	0.0505 (8)
H4B	0.0395	0.1128	−0.1286	0.061*
C5	0.1084 (2)	0.0554 (4)	0.0021 (2)	0.0475 (8)
H5A	0.1095	−0.0517	−0.0067	0.057*
C6	0.14879 (19)	0.1216 (3)	0.08851 (19)	0.0341 (6)
C7	0.2186 (2)	0.1743 (3)	0.23568 (19)	0.0347 (6)
C8	0.2706 (2)	0.1519 (3)	0.3365 (2)	0.0422 (7)
H8A	0.2554	0.0498	0.3555	0.051*
H8B	0.2490	0.2292	0.3721	0.051*
C9	0.3775 (2)	0.1656 (3)	0.3583 (2)	0.0443 (8)
H9A	0.4072	0.1164	0.4179	0.053*
H9B	0.3960	0.1065	0.3121	0.053*
C10	0.4171 (2)	0.3257 (3)	0.36158 (19)	0.0350 (6)
C11	0.44533 (19)	0.5716 (3)	0.34521 (19)	0.0341 (6)
C12	0.4432 (2)	0.7294 (3)	0.3244 (2)	0.0425 (7)
H12A	0.3869	0.7788	0.2916	0.051*
C13	0.5285 (2)	0.8104 (4)	0.3544 (2)	0.0510 (8)
H13A	0.5290	0.9162	0.3412	0.061*
C14	0.6132 (2)	0.7376 (4)	0.4037 (2)	0.0531 (9)
H14A	0.6688	0.7961	0.4229	0.064*
C15	0.6167 (2)	0.5823 (4)	0.4248 (2)	0.0477 (8)
H15A	0.6733	0.5334	0.4574	0.057*
C16	0.5313 (2)	0.5015 (3)	0.3947 (2)	0.0373 (7)
C17	0.0792 (2)	0.7964 (4)	0.3494 (3)	0.0570 (9)
H17A	0.0632	0.7570	0.4020	0.086*
H17B	0.0221	0.8147	0.2992	0.086*
H17C	0.1137	0.8923	0.3659	0.086*
C18	0.1398 (2)	0.6794 (3)	0.32005 (19)	0.0370 (7)

	U11	U22	U33	U12	U13	U23
Cu1	0.0287 (2)	0.0265 (2)	0.0330 (2)	0.00279 (13)	0.00674 (14)	−0.00318 (13)
N1	0.0321 (12)	0.0269 (12)	0.0326 (12)	−0.0002 (10)	0.0068 (10)	0.0016 (9)
N2	0.0431 (15)	0.0224 (12)	0.0477 (15)	−0.0004 (11)	0.0084 (12)	0.0008 (11)
N3	0.0293 (13)	0.0349 (13)	0.0367 (13)	0.0051 (10)	0.0094 (10)	−0.0012 (10)
N4	0.0310 (13)	0.0421 (14)	0.0404 (14)	0.0097 (11)	0.0026 (10)	0.0034 (11)
O1	0.0339 (12)	0.0483 (13)	0.0463 (12)	0.0038 (9)	0.0093 (9)	−0.0152 (10)
O2	0.0349 (11)	0.0407 (11)	0.0425 (11)	0.0016 (9)	0.0083 (9)	−0.0051 (10)
O3	0.0454 (13)	0.0499 (13)	0.0435 (12)	0.0003 (10)	0.0083 (10)	0.0003 (10)
Cl1	0.0658 (5)	0.0305 (4)	0.0414 (4)	−0.0017 (3)	0.0180 (4)	0.0043 (3)
C1	0.0261 (14)	0.0266 (13)	0.0374 (14)	−0.0026 (11)	0.0111 (11)	−0.0025 (11)
C2	0.0356 (16)	0.0307 (15)	0.0403 (16)	−0.0019 (12)	0.0050 (12)	0.0024 (12)
C3	0.0442 (19)	0.0492 (19)	0.0420 (17)	−0.0032 (15)	0.0044 (14)	0.0054 (14)
C4	0.051 (2)	0.056 (2)	0.0385 (17)	−0.0067 (16)	0.0050 (14)	−0.0139 (15)
C5	0.0467 (19)	0.0378 (17)	0.055 (2)	−0.0022 (15)	0.0107 (15)	−0.0136 (15)
C6	0.0318 (15)	0.0290 (14)	0.0405 (15)	0.0011 (12)	0.0096 (12)	−0.0041 (12)
C7	0.0343 (16)	0.0301 (15)	0.0381 (15)	−0.0011 (12)	0.0088 (12)	0.0032 (12)
C8	0.0473 (19)	0.0364 (16)	0.0405 (16)	−0.0020 (14)	0.0098 (14)	0.0107 (13)
C9	0.0460 (19)	0.0359 (16)	0.0437 (17)	0.0075 (14)	0.0031 (14)	0.0076 (13)
C10	0.0330 (15)	0.0387 (16)	0.0319 (14)	0.0058 (12)	0.0081 (12)	0.0003 (12)
C11	0.0264 (14)	0.0387 (16)	0.0363 (15)	0.0014 (12)	0.0082 (11)	−0.0053 (12)
C12	0.0344 (16)	0.0404 (17)	0.0521 (18)	0.0016 (13)	0.0125 (14)	−0.0040 (14)
C13	0.0449 (19)	0.0432 (19)	0.068 (2)	−0.0056 (15)	0.0222 (17)	−0.0068 (16)
C14	0.0349 (18)	0.063 (2)	0.064 (2)	−0.0098 (16)	0.0190 (16)	−0.0125 (18)
C15	0.0281 (16)	0.059 (2)	0.0528 (19)	0.0062 (15)	0.0073 (13)	−0.0038 (16)
C16	0.0311 (15)	0.0444 (18)	0.0364 (15)	0.0049 (13)	0.0107 (12)	−0.0034 (13)
C17	0.053 (2)	0.056 (2)	0.067 (2)	0.0192 (17)	0.0255 (18)	−0.0051 (18)
C18	0.0407 (17)	0.0375 (16)	0.0349 (15)	0.0069 (13)	0.0150 (13)	0.0021 (13)

Cu1—N1	1.969 (2)	C4—C5	1.362 (4)
Cu1—N3	2.006 (2)	C4—H4B	0.9300
Cu1—O2	2.053 (2)	C5—C6	1.382 (4)
Cu1—O1	2.0546 (19)	C5—H5A	0.9300
Cu1—C18	2.387 (3)	C7—C8	1.496 (4)
Cu1—Cl1	2.4836 (8)	C8—C9	1.517 (4)
N1—C7	1.320 (3)	C8—H8A	0.9700
N1—C1	1.392 (3)	C8—H8B	0.9700
N2—C7	1.335 (4)	C9—C10	1.489 (4)
N2—C6	1.379 (3)	C9—H9A	0.9700
N2—H2A	0.8600	C9—H9B	0.9700
N3—C10	1.336 (3)	C11—C12	1.389 (4)
N3—C11	1.405 (4)	C11—C16	1.397 (4)
N4—C10	1.336 (4)	C12—C13	1.387 (4)
N4—C16	1.375 (4)	C12—H12A	0.9300
N4—H4A	0.8600	C13—C14	1.393 (5)
O1—C18	1.267 (3)	C13—H13A	0.9300
O2—C18	1.252 (3)	C14—C15	1.368 (5)
O3—H1W	0.8200	C14—H14A	0.9300
O3—H2W	0.8199	C15—C16	1.389 (4)
C1—C2	1.389 (4)	C15—H15A	0.9300
C1—C6	1.400 (4)	C17—C18	1.502 (4)
C2—C3	1.378 (4)	C17—H17A	0.9600
C2—H2B	0.9300	C17—H17B	0.9600
C3—C4	1.389 (4)	C17—H17C	0.9600
C3—H3A	0.9300
N1—Cu1—N3	98.48 (9)	N1—C7—N2	112.2 (2)
N1—Cu1—O2	95.78 (9)	N1—C7—C8	123.8 (2)
N3—Cu1—O2	153.13 (9)	N2—C7—C8	123.9 (2)
N1—Cu1—O1	155.25 (9)	C7—C8—C9	112.6 (3)
N3—Cu1—O1	95.98 (9)	C7—C8—H8A	109.1
O2—Cu1—O1	63.62 (8)	C9—C8—H8A	109.1
N1—Cu1—C18	126.68 (10)	C7—C8—H8B	109.1
N3—Cu1—C18	126.69 (10)	C9—C8—H8B	109.1
O2—Cu1—C18	31.63 (9)	H8A—C8—H8B	107.8
O1—Cu1—C18	32.06 (9)	C10—C9—C8	116.9 (2)
N1—Cu1—Cl1	104.57 (7)	C10—C9—H9A	108.1
N3—Cu1—Cl1	105.94 (7)	C8—C9—H9A	108.1
O2—Cu1—Cl1	92.25 (6)	C10—C9—H9B	108.1
O1—Cu1—Cl1	90.52 (7)	C8—C9—H9B	108.1
C18—Cu1—Cl1	90.03 (7)	H9A—C9—H9B	107.3
C7—N1—C1	106.1 (2)	N4—C10—N3	111.7 (3)
C7—N1—Cu1	123.01 (18)	N4—C10—C9	118.8 (2)
C1—N1—Cu1	130.73 (17)	N3—C10—C9	129.4 (3)
C7—N2—C6	108.1 (2)	C12—C11—C16	119.6 (3)
C7—N2—H2A	126.0	C12—C11—N3	131.8 (3)
C6—N2—H2A	126.0	C16—C11—N3	108.5 (2)
C10—N3—C11	105.4 (2)	C13—C12—C11	117.4 (3)
C10—N3—Cu1	132.1 (2)	C13—C12—H12A	121.3
C11—N3—Cu1	122.28 (18)	C11—C12—H12A	121.3
C10—N4—C16	108.8 (2)	C12—C13—C14	121.8 (3)
C10—N4—H4A	125.6	C12—C13—H13A	119.1
C16—N4—H4A	125.6	C14—C13—H13A	119.1
C18—O1—Cu1	88.55 (16)	C15—C14—C13	121.7 (3)
C18—O2—Cu1	89.06 (17)	C15—C14—H14A	119.2
H1W—O3—H2W	102.3	C13—C14—H14A	119.2
C2—C1—N1	132.0 (2)	C14—C15—C16	116.4 (3)
C2—C1—C6	119.8 (2)	C14—C15—H15A	121.8
N1—C1—C6	108.2 (2)	C16—C15—H15A	121.8
C3—C2—C1	117.5 (3)	N4—C16—C15	131.4 (3)
C3—C2—H2B	121.3	N4—C16—C11	105.5 (3)
C1—C2—H2B	121.3	C15—C16—C11	123.1 (3)
C2—C3—C4	121.8 (3)	C18—C17—H17A	109.5
C2—C3—H3A	119.1	C18—C17—H17B	109.5
C4—C3—H3A	119.1	H17A—C17—H17B	109.5
C5—C4—C3	121.5 (3)	C18—C17—H17C	109.5
C5—C4—H4B	119.3	H17A—C17—H17C	109.5
C3—C4—H4B	119.3	H17B—C17—H17C	109.5
C4—C5—C6	117.2 (3)	O2—C18—O1	118.5 (3)
C4—C5—H5A	121.4	O2—C18—C17	121.1 (3)
C6—C5—H5A	121.4	O1—C18—C17	120.4 (3)
N2—C6—C5	132.4 (3)	O2—C18—Cu1	59.32 (14)
N2—C6—C1	105.5 (2)	O1—C18—Cu1	59.39 (14)
C5—C6—C1	122.2 (3)	C17—C18—Cu1	174.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1W···Cl1	0.82	2.32	3.132 (2)	173.
N2—H2A···Cl1i	0.86	2.44	3.203 (2)	149.
N4—H4A···O3ii	0.86	1.93	2.786 (3)	172.
O3—H2W···O1iii	0.82	2.00	2.822 (3)	176.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1W⋯Cl1	0.82	2.32	3.132 (2)	173
N2—H2A⋯Cl1i	0.86	2.44	3.203 (2)	149
N4—H4A⋯O3ii	0.86	1.93	2.786 (3)	172
O3—H2W⋯O1iii	0.82	2.00	2.822 (3)	176

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