{2-[6-(1H-Benzimidazol-2-yl-κN3)-2-pyridyl-κN]benzimidazolato-κN}(dicyanamido-κN)(methanol-κO)copper(II)

Hu, J.; Zhang, J.; Zhang, W.; Zhang, C.

doi:10.1107/S1600536810050178

metal-organic compounds

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Volume 67| Part 1| January 2011| Page m61

https://doi.org/10.1107/S1600536810050178

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{2-[6-(1H-Benzimidazol-2-yl-κN³)-2-pyridyl-κN]benzimidazolato-κN}(dicyanamido-κN)(methanol-κO)copper(II)

Jingchun Hu,^a Jinfang Zhang,^a Weiming Zhang ^a and Chi Zhang ^a ^*

^aMolecular Materials Research Center, Scientific Research Academy, School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, People's Republic of China
^*Correspondence e-mail: chizhang@ujs.edu.cn

(Received 16 November 2010; accepted 1 December 2010; online 11 December 2010)

In the title compound, [Cu(C₁₉H₁₂N₅)(C₂N₃)(CH₃OH)], 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 molecule 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 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(C₁₉H₁₂N₅)(C₂N₃)(CH₄O)]
M_r = 471.98
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.030
wR(F²) = 0.072
S = 1.02
3591 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.28 e Å⁻³

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) -x, -y, -z; (ii) x, y+1, z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810050178/bt5405sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050178/bt5405Isup2.hkl

checkCIF report

Comment top

Benzimidazole derivatives and their metal complexes have attracted considerable interest over several decades, because many of these materials have been applied to various fields such as biological systems (Khaled, 2003; Hay et al., 1998), Luminescent (Petoud et al., 1997; Liu et al., 2005), and magnetic properties (Boinnard et al., 1990; Mo et al., 2009). 2,6-bis(2-benzimidazol-2-yl)pyridine(bbp) (Addison et al., 1981) as a benzimidazole derivative, is a tridentate ligand with two benzimidazole and one pyridine nitrogen atoms. In this paper, we report the structue of a new Cu^II complex based on bbp ligand.

Figure 1 shows that the Cu^II atom is coordinated by N1, N2 and N4 from the tridentate bbp ligand and N6 from the dicyanamide anion, and O1 from one methanol molecule. The distance of Cu-N bonds range from 1.9528 (19) to 2.0364 (2) Å. While the Cu-N1, Cu-N2 and Cu-N4 distances are 1.9763 (18), 2.0364 (19), 1.9955 (19) Å, respectively; and the N1-Cu-N2 and N1-Cu-N4 angles are 79.36 (7), 79.51 (7)°, respectively, these parameters are similar to those reported for other bbp-containing complexes (Wang et al., 1994; Bernardinelli et al., 1990). Due to intermolecular hydrogen-bonding interactions, the crystal structure is extended to a three-dimensional network (Figure 2).

Related literature top

For potential applications of benzimidazole derivatives and their 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 top

The bbp (0.1 mmol) and CuClO₄.6H₂O (0.1 mmol) were added to 3 ml dimethylformamide with thorough stirring for 2 minutes. After filtering, the filtrate was carefully layered with 0.5 ml dimethylformamide and 5 ml methanol solution of Sodium dicyanamide (0.2 mol L^-1), in turn. Green crystals suitable for X-ray analysis were obtained after one week. Elemental analysis found: C 55.56, H 3.33, N 23.46%; calculated for C₂₂H₁₆CuN₈O: C 55.98, H 3.42, N 23.75%.

Structure description top

For potential applications of benzimidazole derivatives and their 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).

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids. All H atoms have been omitted.
	Fig. 2. The packing diagram of the title compound.

{2-[6-(1H-Benzimidazol-2-yl-κN³)-2-pyridyl- κN]benzimidazolato-κN}(dicyanamido-κN)(methanol- κO)copper(II) top

Crystal data top

[Cu(C₁₉H₁₂N₅)(C₂N₃)(CH₄O)]	Z = 2
M_r = 471.98	F(000) = 482
Triclinic, P1	D_x = 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

Data collection top

Rigaku Saturn724 diffractometer	3591 independent reflections
Radiation source: fine-focus sealed tube	3294 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 25.3°, θ_min = 3.4°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	h = −8→7
T_min = 0.806, T_max = 0.874	k = −14→14
7787 measured reflections	l = −15→13

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.072	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0326P)² + 0.7506P] where P = (F_o² + 2F_c²)/3
3591 reflections	(Δ/σ)_max < 0.001
290 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

[Cu(C₁₉H₁₂N₅)(C₂N₃)(CH₄O)]	γ = 97.12 (3)°
M_r = 471.98	V = 1001.2 (4) Å³
Triclinic, P1	Z = 2
a = 6.8262 (14) Å	Mo Kα radiation
b = 12.189 (2) Å	µ = 1.13 mm⁻¹
c = 12.609 (3) Å	T = 293 K
α = 101.74 (3)°	0.2 × 0.16 × 0.12 mm
β = 99.03 (3)°

Data collection top

Rigaku Saturn724 diffractometer	3591 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	3294 reflections with I > 2σ(I)
T_min = 0.806, T_max = 0.874	R_int = 0.020
7787 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.072	H-atom parameters constrained
S = 1.02	Δρ_max = 0.52 e Å⁻³
3591 reflections	Δρ_min = −0.28 e Å⁻³
290 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y, −z; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₉H₁₂N₅)(C₂N₃)(CH₄O)]
M_r	471.98
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.8262 (14), 12.189 (2), 12.609 (3)
α, β, γ (°)	101.74 (3), 99.03 (3), 97.12 (3)
V (Å³)	1001.2 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.13
Crystal size (mm)	0.2 × 0.16 × 0.12

Data collection
Diffractometer	Rigaku Saturn724
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2007)
T_min, T_max	0.806, 0.874
No. of measured, independent and observed [I > 2σ(I)] reflections	7787, 3591, 3294
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.072, 1.02
No. of reflections	3591
No. of parameters	290
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.28

Computer programs: CrystalClear (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N5ⁱ	0.82	1.93	2.743 (3)	172.0
N3—H3A···N8ⁱⁱ	0.86	1.96	2.807 (3)	166.3

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

Acknowledgements

This work was supported by the National Natural Science Foundation of China for Distinguished Young Scholars Fund (to CZ; 50925207), the Ministry of Science and Technology of China for the International Science Linkages Program (2009DFA50620), the Special Fund for International Collaboration & Exchange of Jiangsu Province (BZ2008049) and the UJS who are gratefully acknowledged.

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