{2-[6-(1H-Benzimidazol-2-yl-κN)-2-pyridyl-κN]benzimidazolato-κN}(dicyanamido-κN)(methanol-κO)copper(II).

In the title compound, [Cu(C(19)H(12)N(5))(C(2)N(3))(CH(3)OH)], the Cu(II) atom is coordinated by three N atoms from an anionic 2,6-bis-(1H-benzimidazol-2-yl)pyridine (bbp) ligand, an O atom from a methanol mol-ecule and one N atom from a dicyanamide anion. The crystal structure is stabilized by O-H⋯N and N-H⋯N hydrogen bonds, forming a three-dimensional network.

Related literature

For potential applications of benzimidazole derivatives and their n class="Chemical">metal complexes, see: Khaled (2003 ▶); Hay et al. (1998 ▶); Petoud et al. (1997 ▶); Liu et al. (2005 ▶); Boinnard et al. (1990 ▶); Mo et al. (2009 ▶); Addison & Burke (1981 ▶). For examples of other bbp-containing complexes, see: Wang et al. (1994 ▶); Bernardinelli et al. (1990 ▶).

Experimental

Crystal data

[Cu(C19n class="Species">H12N5)(C2N3)(CH4O)]

M = 471.98

Triclinic,

a = 6.8262 (14) Å

b = 12.189 (2) Å

c = 12.609 (3) Å

α = 101.74 (3)°

β = 99.03 (3)°

γ = 97.12 (3)°

V = 1001.2 (4) Å3

Z = 2

Mo Kα radiation

μ = 1.13 mm−1

T = 293 K

0.20 × 0.16 × 0.12 mm

Data collection

Rigaku Saturn724 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ▶) T min = 0.806, T max = 0.874

7787 measured reflections

3591 independent reflections

3294 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.072

S = 1.02

3591 reflections

290 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrystalClear (Rigaku, 2007 ▶); 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 I, global. DOI: 10.1107/S1600536810050178/bt5405sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050178/bt5405Isup2.hkl

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

[Cu(C19H12N5)(C2N3)(CH4O)]	Z = 2
Mr = 471.98	F(000) = 482
Triclinic, P1	Dx = 1.566 Mg m−3
a = 6.8262 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.189 (2) Å	Cell parameters from 4368 reflections
c = 12.609 (3) Å	θ = 3.5–29.1°
α = 101.74 (3)°	µ = 1.13 mm−1
β = 99.03 (3)°	T = 293 K
γ = 97.12 (3)°	Block, green
V = 1001.2 (4) Å3	0.2 × 0.16 × 0.12 mm

Rigaku Saturn724 diffractometer	3591 independent reflections
Radiation source: fine-focus sealed tube	3294 reflections with I > 2σ(I)
graphite	Rint = 0.020
ω scans	θmax = 25.3°, θmin = 3.4°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	h = −8→7
Tmin = 0.806, Tmax = 0.874	k = −14→14
7787 measured reflections	l = −15→13

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0326P)2 + 0.7506P] where P = (Fo2 + 2Fc2)/3
3591 reflections	(Δ/σ)max < 0.001
290 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.40402 (4)	0.04545 (2)	0.20901 (2)	0.01736 (10)
O1	0.1127 (2)	0.03746 (13)	0.27080 (12)	0.0254 (4)
H1	0.0241	0.0546	0.2282	0.030*
N1	0.3511 (3)	0.14654 (14)	0.10718 (14)	0.0168 (4)
N2	0.5225 (3)	0.19964 (14)	0.31068 (14)	0.0196 (4)
N3	0.5742 (3)	0.38708 (14)	0.32891 (15)	0.0225 (4)
H3A	0.5719	0.4521	0.3125	0.027*
N4	0.2876 (3)	−0.06889 (14)	0.06878 (14)	0.0178 (4)
N5	0.1565 (3)	−0.09661 (14)	−0.11513 (14)	0.0188 (4)
N6	0.5284 (3)	−0.05076 (15)	0.29717 (15)	0.0246 (4)
N7	0.7320 (3)	−0.19234 (16)	0.34181 (17)	0.0307 (5)
N8	0.6356 (4)	−0.39938 (18)	0.2773 (2)	0.0430 (6)
C1	0.2400 (3)	−0.18446 (17)	0.02561 (17)	0.0171 (4)
C2	0.2565 (3)	−0.27628 (17)	0.07551 (19)	0.0203 (5)
H2A	0.3067	−0.2652	0.1505	0.024*
C3	0.1956 (3)	−0.38377 (18)	0.0091 (2)	0.0247 (5)
H3B	0.2048	−0.4464	0.0401	0.030*
C4	0.1200 (3)	−0.40094 (19)	−0.1044 (2)	0.0260 (5)
H4A	0.0827	−0.4747	−0.1469	0.031*
C5	0.0996 (3)	−0.31132 (19)	−0.15430 (19)	0.0238 (5)
H5B	0.0478	−0.3233	−0.2292	0.029*
C6	0.1599 (3)	−0.20125 (17)	−0.08783 (17)	0.0181 (4)
C7	0.2323 (3)	−0.02371 (17)	−0.01919 (17)	0.0166 (4)
C8	0.2646 (3)	0.10090 (17)	0.00213 (17)	0.0172 (4)
C9	0.2181 (3)	0.17004 (18)	−0.07045 (18)	0.0203 (5)
H9A	0.1545	0.1389	−0.1431	0.024*
C10	0.2695 (3)	0.28666 (18)	−0.03130 (19)	0.0225 (5)
H10A	0.2409	0.3345	−0.0785	0.027*
C11	0.3629 (3)	0.33284 (18)	0.07713 (19)	0.0211 (5)
H11A	0.3985	0.4110	0.1033	0.025*
C12	0.4016 (3)	0.25952 (17)	0.14528 (18)	0.0185 (5)
C13	0.4982 (3)	0.28491 (17)	0.26130 (18)	0.0186 (5)
C14	0.6564 (3)	0.36794 (18)	0.42919 (19)	0.0240 (5)
C15	0.7569 (4)	0.4417 (2)	0.5265 (2)	0.0351 (6)
H15A	0.7786	0.5200	0.5337	0.042*
C16	0.8230 (4)	0.3930 (2)	0.6122 (2)	0.0400 (7)
H16A	0.8917	0.4398	0.6788	0.048*
C17	0.7900 (4)	0.2751 (2)	0.6023 (2)	0.0343 (6)
H17A	0.8374	0.2457	0.6621	0.041*
C18	0.6886 (4)	0.2019 (2)	0.50539 (19)	0.0272 (5)
H18A	0.6655	0.1238	0.4991	0.033*
C19	0.6224 (3)	0.24939 (18)	0.41759 (18)	0.0209 (5)
C20	0.6166 (3)	−0.12164 (18)	0.31518 (17)	0.0205 (5)
C21	0.6717 (4)	−0.3023 (2)	0.3061 (2)	0.0273 (5)
C22	0.1031 (4)	0.0833 (2)	0.3824 (2)	0.0383 (6)
H22A	0.1013	0.1634	0.3931	0.057*
H22B	0.2185	0.0705	0.4297	0.057*
H22C	−0.0169	0.0470	0.3999	0.057*

	U11	U22	U33	U12	U13	U23
Cu1	0.02205 (16)	0.01322 (14)	0.01587 (15)	0.00307 (10)	0.00051 (11)	0.00332 (10)
O1	0.0220 (8)	0.0372 (9)	0.0165 (8)	0.0072 (7)	0.0009 (7)	0.0057 (7)
N1	0.0174 (9)	0.0157 (9)	0.0182 (9)	0.0033 (7)	0.0042 (7)	0.0049 (7)
N2	0.0220 (10)	0.0169 (9)	0.0190 (10)	0.0037 (7)	0.0017 (8)	0.0033 (7)
N3	0.0276 (10)	0.0132 (9)	0.0256 (11)	0.0029 (8)	0.0044 (8)	0.0026 (7)
N4	0.0181 (9)	0.0161 (9)	0.0180 (9)	0.0017 (7)	0.0021 (8)	0.0031 (7)
N5	0.0165 (9)	0.0222 (9)	0.0171 (9)	0.0033 (7)	0.0029 (8)	0.0029 (7)
N6	0.0330 (11)	0.0158 (9)	0.0234 (10)	0.0036 (8)	−0.0005 (9)	0.0055 (8)
N7	0.0317 (12)	0.0227 (10)	0.0371 (12)	0.0092 (9)	−0.0029 (9)	0.0101 (9)
N8	0.0559 (16)	0.0243 (12)	0.0550 (16)	0.0137 (11)	0.0164 (13)	0.0145 (10)
C1	0.0143 (10)	0.0155 (10)	0.0203 (11)	0.0013 (8)	0.0048 (9)	0.0007 (8)
C2	0.0178 (11)	0.0203 (11)	0.0225 (12)	0.0026 (9)	0.0031 (9)	0.0045 (9)
C3	0.0220 (12)	0.0171 (11)	0.0344 (14)	0.0023 (9)	0.0060 (10)	0.0047 (9)
C4	0.0228 (12)	0.0175 (11)	0.0318 (13)	−0.0002 (9)	0.0029 (10)	−0.0037 (9)
C5	0.0195 (12)	0.0258 (12)	0.0214 (12)	0.0005 (9)	0.0028 (10)	−0.0027 (9)
C6	0.0145 (11)	0.0201 (11)	0.0194 (11)	0.0019 (8)	0.0057 (9)	0.0026 (8)
C7	0.0142 (10)	0.0195 (10)	0.0166 (11)	0.0039 (8)	0.0030 (9)	0.0044 (8)
C8	0.0133 (11)	0.0200 (11)	0.0186 (11)	0.0021 (8)	0.0048 (9)	0.0040 (8)
C9	0.0188 (11)	0.0266 (12)	0.0176 (11)	0.0048 (9)	0.0047 (9)	0.0080 (9)
C10	0.0218 (12)	0.0249 (12)	0.0272 (12)	0.0087 (9)	0.0083 (10)	0.0145 (9)
C11	0.0211 (12)	0.0170 (11)	0.0281 (12)	0.0063 (9)	0.0074 (10)	0.0079 (9)
C12	0.0170 (11)	0.0172 (10)	0.0222 (12)	0.0041 (9)	0.0061 (9)	0.0040 (8)
C13	0.0203 (11)	0.0143 (10)	0.0217 (11)	0.0032 (8)	0.0066 (9)	0.0029 (8)
C14	0.0231 (12)	0.0228 (11)	0.0241 (12)	0.0029 (9)	0.0052 (10)	0.0006 (9)
C15	0.0378 (15)	0.0275 (13)	0.0315 (14)	−0.0026 (11)	0.0034 (12)	−0.0057 (10)
C16	0.0400 (16)	0.0421 (15)	0.0256 (14)	−0.0023 (13)	−0.0029 (12)	−0.0080 (11)
C17	0.0317 (14)	0.0474 (16)	0.0207 (13)	0.0069 (12)	−0.0010 (11)	0.0051 (11)
C18	0.0277 (13)	0.0302 (13)	0.0228 (13)	0.0058 (10)	0.0022 (10)	0.0053 (10)
C19	0.0188 (11)	0.0222 (11)	0.0195 (12)	0.0026 (9)	0.0028 (9)	0.0009 (9)
C20	0.0255 (12)	0.0174 (11)	0.0157 (11)	−0.0016 (9)	0.0006 (9)	0.0023 (8)
C21	0.0322 (14)	0.0256 (13)	0.0295 (13)	0.0108 (10)	0.0080 (11)	0.0128 (10)
C22	0.0356 (15)	0.0572 (17)	0.0196 (13)	0.0053 (13)	0.0073 (11)	0.0028 (12)

Cu1—N6	1.9528 (19)	C3—H3B	0.9300
Cu1—N1	1.9763 (18)	C4—C5	1.378 (3)
Cu1—N4	1.9955 (19)	C4—H4A	0.9300
Cu1—N2	2.0364 (19)	C5—C6	1.403 (3)
Cu1—O1	2.2452 (16)	C5—H5B	0.9300
O1—C22	1.420 (3)	C7—C8	1.470 (3)
O1—H1	0.8200	C8—C9	1.392 (3)
N1—C8	1.336 (3)	C9—C10	1.387 (3)
N1—C12	1.344 (3)	C9—H9A	0.9300
N2—C13	1.330 (3)	C10—C11	1.384 (3)
N2—C19	1.388 (3)	C10—H10A	0.9300
N3—C13	1.348 (3)	C11—C12	1.381 (3)
N3—C14	1.378 (3)	C11—H11A	0.9300
N3—H3A	0.8601	C12—C13	1.461 (3)
N4—C7	1.358 (3)	C14—C15	1.386 (3)
N4—C1	1.380 (3)	C14—C19	1.408 (3)
N5—C7	1.331 (3)	C15—C16	1.377 (4)
N5—C6	1.389 (3)	C15—H15A	0.9300
N6—C20	1.151 (3)	C16—C17	1.404 (4)
N7—C20	1.296 (3)	C16—H16A	0.9300
N7—C21	1.315 (3)	C17—C18	1.380 (3)
N8—C21	1.148 (3)	C17—H17A	0.9300
C1—C2	1.399 (3)	C18—C19	1.390 (3)
C1—C6	1.412 (3)	C18—H18A	0.9300
C2—C3	1.378 (3)	C22—H22A	0.9600
C2—H2A	0.9300	C22—H22B	0.9600
C3—C4	1.406 (3)	C22—H22C	0.9600
N6—Cu1—N1	164.13 (8)	N5—C7—C8	127.12 (19)
N6—Cu1—N4	100.45 (8)	N4—C7—C8	116.10 (18)
N1—Cu1—N4	79.51 (7)	N1—C8—C9	120.47 (19)
N6—Cu1—N2	98.73 (8)	N1—C8—C7	110.70 (18)
N1—Cu1—N2	79.36 (7)	C9—C8—C7	128.83 (19)
N4—Cu1—N2	158.46 (7)	C10—C9—C8	118.1 (2)
N6—Cu1—O1	97.03 (7)	C10—C9—H9A	121.0
N1—Cu1—O1	98.82 (7)	C8—C9—H9A	121.0
N4—Cu1—O1	93.63 (7)	C11—C10—C9	120.9 (2)
N2—Cu1—O1	93.64 (7)	C11—C10—H10A	119.6
C22—O1—Cu1	122.14 (14)	C9—C10—H10A	119.6
C22—O1—H1	111.5	C12—C11—C10	118.1 (2)
Cu1—O1—H1	111.4	C12—C11—H11A	121.0
C8—N1—C12	121.54 (18)	C10—C11—H11A	121.0
C8—N1—Cu1	119.15 (14)	N1—C12—C11	120.9 (2)
C12—N1—Cu1	119.31 (14)	N1—C12—C13	109.69 (18)
C13—N2—C19	105.85 (17)	C11—C12—C13	129.39 (19)
C13—N2—Cu1	112.46 (14)	N2—C13—N3	112.53 (19)
C19—N2—Cu1	141.69 (15)	N2—C13—C12	119.10 (18)
C13—N3—C14	107.20 (18)	N3—C13—C12	128.36 (19)
C13—N3—H3A	126.4	N3—C14—C15	131.6 (2)
C14—N3—H3A	126.4	N3—C14—C19	106.14 (19)
C7—N4—C1	103.53 (17)	C15—C14—C19	122.3 (2)
C7—N4—Cu1	114.48 (13)	C16—C15—C14	116.4 (2)
C1—N4—Cu1	141.98 (15)	C16—C15—H15A	121.8
C7—N5—C6	102.69 (17)	C14—C15—H15A	121.8
C20—N6—Cu1	156.97 (18)	C15—C16—C17	122.1 (2)
C20—N7—C21	120.2 (2)	C15—C16—H16A	118.9
N4—C1—C2	131.1 (2)	C17—C16—H16A	118.9
N4—C1—C6	107.57 (18)	C18—C17—C16	121.3 (2)
C2—C1—C6	121.29 (19)	C18—C17—H17A	119.4
C3—C2—C1	117.4 (2)	C16—C17—H17A	119.4
C3—C2—H2A	121.3	C17—C18—C19	117.5 (2)
C1—C2—H2A	121.3	C17—C18—H18A	121.3
C2—C3—C4	121.5 (2)	C19—C18—H18A	121.3
C2—C3—H3B	119.2	N2—C19—C18	131.3 (2)
C4—C3—H3B	119.2	N2—C19—C14	108.28 (19)
C5—C4—C3	121.7 (2)	C18—C19—C14	120.5 (2)
C5—C4—H4A	119.1	N6—C20—N7	173.5 (2)
C3—C4—H4A	119.1	N8—C21—N7	174.3 (3)
C4—C5—C6	117.5 (2)	O1—C22—H22A	109.5
C4—C5—H5B	121.2	O1—C22—H22B	109.5
C6—C5—H5B	121.2	H22A—C22—H22B	109.5
N5—C6—C5	130.0 (2)	O1—C22—H22C	109.5
N5—C6—C1	109.42 (18)	H22A—C22—H22C	109.5
C5—C6—C1	120.6 (2)	H22B—C22—H22C	109.5
N5—C7—N4	116.78 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N5i	0.82	1.93	2.743 (3)	172.
N3—H3A···N8ii	0.86	1.96	2.807 (3)	166.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N5i	0.82	1.93	2.743 (3)	172
N3—H3A⋯N8ii	0.86	1.96	2.807 (3)	166

Symmetry codes: (i) ; (ii) .