{N′-[(2-Oxidonaphthalen-1-yl)methyl­idene]benzohydrazidato}(1,10-phenanthroline)copper(II) methanol monosolvate

Liu, B.-L.; Dong, D.-M.; Hua, X.-Y.; Zhu, J.-W.

doi:10.1107/S1600536811054316

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page m86

doi:10.1107/S1600536811054316

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{N′-[(2-Oxidonaphthalen-1-yl)methylidene]benzohydrazidato}(1,10-phenanthroline)copper(II) methanol monosolvate

Bao-Lin Liu,^a De-Ming Dong,^a Xiu-Yi Hua ^a and Jian-Wei Zhu ^b ^*

^aCollege of Environment and Resources, Jilin University, Changchun 130012, People's Republic of China, and ^bCollege of Earth Sciences, Jilin University, Changchun 130061, People's Republic of China
^*Correspondence e-mail: jianweizhu1905@163.com

(Received 3 December 2011; accepted 17 December 2011; online 23 December 2011)

The title mononuclear complex, [Cu(C₁₈H₁₂N₂O₂)(C₁₂H₈N₂)]·CH₃OH, contains one N′-[(2-oxidonaphthalen-1-yl)methylidene]benzohydrazidate ligand (L²⁻), a Cu²⁺ cation, one 1,10-phenanthroline ligand and a methanol solvent molecule. The Cu^II ion adopts a CuO₂N₃ distorted square-pyramidal coordination. An O—H⋯O hydrogen bond is formed between the methanol solvent molecule and the hydrazide O atom of the L²⁻ ligand.

Related literature

For details of the preparation of the Schiff base, see: Qiao et al. (2010 ). For applications of Schiff base compounds, see: Anford et al. (1998 ); Guo et al. (2010 ). For related structures, see: Huo et al. (2004 ); Liu et al. (2008 ); Sreeja et al. (2004 ).

Experimental

Crystal data

[Cu(C₁₈H₁₂N₂O₂)(C₁₂H₈N₂)]·CH₄O
M_r = 564.08
Monoclinic, P 2₁ /c
a = 20.388 (2) Å
b = 9.9707 (10) Å
c = 12.5268 (12) Å
β = 105.035 (2)°
V = 2459.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.93 mm⁻¹
T = 185 K
0.20 × 0.18 × 0.17 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.836, T_max = 0.858
12077 measured reflections
4352 independent reflections
2950 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.093
S = 1.02
4352 reflections
354 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O2	1.913 (2)
Cu1—N2	1.914 (2)
Cu1—O1	1.984 (2)
Cu1—N4	2.023 (3)
Cu1—N3	2.321 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O1	0.84	1.99	2.820 (3)	167

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811054316/kp2374sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811054316/kp2374Isup2.hkl

checkCIF report

Comment top

The study of transition metal-hydrazone compounds (Huo et al., 2004), in which the acylhydrazone ligands are formed by condensing hydrazine with naphthaldehyde or their derivatives, has attracted considerable attention because of the magnetochemistry and chemical versatility of these compounds (Anford et al., 1998; Guo et al., 2010). We selected acylhydrazone ligand of 2-hydroxy-1-naphthaldehyde benzoylhydrazide (H₂L) to construct coordination polymers with defined geometry. We report here the preparation and crystal structure of the title Schiff base copper(II) compound (Fig. 1, Table 1). The title compound has a distorted square-pyramidal geometry and the central Cu^II is five-coordinated with the two O atoms and one N atom from H₂L and two N atoms from 1,10-phenanthroline. Several mononuclear compounds with similar structures have been reported previously (Sreeja et al., 2004; Liu et al., 2008). The square plane around the Cu1 atom is formed by O₂N₂ donor atoms (O1, O2, N2 and N4 ). The apical position occupied by the second nitrogen atom (N3) of 1,10-phenanthroline with a larger distance than N4. The four basal atoms are coplanar showing a significant distortion from square geometry indicated by the trans-bond angle O1—Cu1—O2 [162.81 (9)°]. Cu^II is displaced from the basal plane in the direction of the axial nitrogen, which is evident from the bond angles of N2—Cu1—N4 [172.79 (11)°] and O1—Cu1—N2 [80.85 (10)°]. The maximum displacements from the least-squares plane through O1, O2, N2 and N4 are -0.0600 (21)Å and 0.1055 (27) Å for atoms O1 and N2, respectively; Cu1 is 0.2104 (4)Å below this plane. O3—H3A···O1 hydrogen bond is formed between the methanol solvent molecule and the O atom of the L^2- ligand (Table 2).

Related literature top

For details of the preparation of the Schiff base, see: Qiao et al. (2010). For applications of Schiff base compounds, see: Anford et al. (1998); Guo et al. (2010). For related structures, see: Huo et al. (2004); Liu et al. (2008); Sreeja et al. (2004).

Experimental top

The 2-hydroxy-1-naphthaldehyde benzoylhydrazide ligand (H₂L) was prepared in a similar manner to the reported procedures (Qiao et al. 2010). The title compound was synthesised by adding Cu(OAc)₂.H₂O (0.1 mmol) to a solution of H₂L (0.1 mmol) and triethylamine (0.1 mmol) in methanol/dichloromethane (1:1 20 mL). After stirring for 3 h, 1,10-phenanthroline (0.1 mmol) was added to the resulting solution. Brown crystals of the title compound were isolated from the solution after two weeks.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

Fig. 1. A view of the title organic compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 40% probability level.

{N'-[(2-Oxidonaphthalen-1-yl)methylidene]benzohydrazidato}(1,10- phenanthroline)copper(II) methanol monosolvate top

Crystal data top

[Cu(C₁₈H₁₂N₂O₂)(C₁₂H₈N₂)]·CH₄O	F(000) = 1164
M_r = 564.08	D_x = 1.523 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3881 reflections
a = 20.388 (2) Å	θ = 2.3–25.1°
b = 9.9707 (10) Å	µ = 0.93 mm⁻¹
c = 12.5268 (12) Å	T = 185 K
β = 105.035 (2)°	Block, brown
V = 2459.4 (4) Å³	0.20 × 0.18 × 0.17 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	4352 independent reflections
Radiation source: fine-focus sealed tube	2950 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
phi and ω scans	θ_max = 25.1°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −21→24
T_min = 0.836, T_max = 0.858	k = −11→10
12077 measured reflections	l = −14→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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0369P)² + 0.1098P] where P = (F_o² + 2F_c²)/3
4352 reflections	(Δ/σ)_max < 0.001
354 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Cu(C₁₈H₁₂N₂O₂)(C₁₂H₈N₂)]·CH₄O	V = 2459.4 (4) Å³
M_r = 564.08	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 20.388 (2) Å	µ = 0.93 mm⁻¹
b = 9.9707 (10) Å	T = 185 K
c = 12.5268 (12) Å	0.20 × 0.18 × 0.17 mm
β = 105.035 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4352 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2950 reflections with I > 2σ(I)
T_min = 0.836, T_max = 0.858	R_int = 0.059
12077 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.093	H-atom parameters constrained
S = 1.02	Δρ_max = 0.34 e Å⁻³
4352 reflections	Δρ_min = −0.32 e Å⁻³
354 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	0.25702 (2)	0.62657 (4)	0.14434 (3)	0.02321 (13)
N2	0.22403 (12)	0.6138 (3)	0.2738 (2)	0.0210 (6)
N4	0.30304 (13)	0.6479 (3)	0.0204 (2)	0.0243 (7)
O1	0.32626 (11)	0.5026 (2)	0.23282 (18)	0.0248 (5)
O2	0.20269 (11)	0.7819 (2)	0.09414 (18)	0.0272 (5)
N1	0.25609 (13)	0.5187 (3)	0.3516 (2)	0.0225 (6)
C22	0.21141 (17)	0.3799 (3)	−0.1607 (3)	0.0281 (8)
C10	0.08817 (15)	0.8615 (3)	0.2718 (3)	0.0201 (7)
C30	0.28412 (16)	0.5641 (3)	−0.0679 (3)	0.0219 (8)
C18	0.15699 (16)	0.8359 (3)	0.1370 (3)	0.0230 (8)
C17	0.12057 (16)	0.9477 (3)	0.0781 (3)	0.0283 (8)
H17	0.1332	0.9819	0.0155	0.034*
C19	0.15462 (17)	0.3786 (4)	0.0142 (3)	0.0334 (9)
H19	0.1345	0.3769	0.0747	0.040*
C29	0.23126 (16)	0.4680 (3)	−0.0704 (3)	0.0223 (8)
N3	0.20374 (13)	0.4662 (3)	0.0168 (2)	0.0237 (7)
C28	0.35071 (17)	0.7391 (3)	0.0217 (3)	0.0298 (8)
H28	0.3632	0.7984	0.0830	0.036*
C7	0.30846 (16)	0.4681 (3)	0.3224 (3)	0.0218 (8)
C6	0.34865 (15)	0.3646 (3)	0.3957 (3)	0.0224 (7)
C5	0.40428 (16)	0.3049 (3)	0.3705 (3)	0.0283 (8)
H5	0.4179	0.3337	0.3073	0.034*
C8	0.17973 (15)	0.6886 (3)	0.3031 (3)	0.0211 (7)
H8	0.1713	0.6720	0.3730	0.025*
C15	0.04909 (16)	0.9624 (3)	0.2047 (3)	0.0253 (8)
C27	0.38318 (17)	0.7519 (4)	−0.0626 (3)	0.0327 (9)
H27	0.4168	0.8190	−0.0590	0.039*
C25	0.31509 (16)	0.5700 (3)	−0.1560 (3)	0.0252 (8)
C9	0.14253 (16)	0.7951 (3)	0.2367 (3)	0.0213 (7)
C24	0.29397 (18)	0.4778 (4)	−0.2454 (3)	0.0337 (9)
H24	0.3152	0.4805	−0.3046	0.040*
C16	0.06880 (17)	1.0053 (3)	0.1098 (3)	0.0294 (8)
H16	0.0448	1.0770	0.0670	0.035*
C4	0.44030 (18)	0.2036 (3)	0.4365 (3)	0.0346 (9)
H4	0.4786	0.1642	0.4187	0.042*
C23	0.24477 (18)	0.3873 (4)	−0.2479 (3)	0.0343 (9)
H23	0.2319	0.3271	−0.3086	0.041*
C12	0.01612 (16)	0.8884 (3)	0.3977 (3)	0.0322 (9)
H12	0.0051	0.8635	0.4642	0.039*
C20	0.13060 (19)	0.2883 (3)	−0.0727 (3)	0.0377 (10)
H20	0.0950	0.2275	−0.0711	0.045*
C21	0.15930 (17)	0.2894 (3)	−0.1600 (3)	0.0352 (9)
H21	0.1438	0.2289	−0.2198	0.042*
C13	−0.02362 (18)	0.9835 (3)	0.3284 (3)	0.0353 (9)
H13	−0.0619	1.0222	0.3466	0.042*
C11	0.07096 (16)	0.8301 (3)	0.3714 (3)	0.0251 (8)
H11	0.0979	0.7675	0.4211	0.030*
C2	0.36495 (18)	0.2189 (3)	0.5537 (3)	0.0336 (9)
H2	0.3510	0.1889	0.6164	0.040*
C1	0.32968 (17)	0.3206 (3)	0.4892 (3)	0.0274 (8)
H1	0.2922	0.3612	0.5084	0.033*
C14	−0.00667 (17)	1.0199 (3)	0.2342 (3)	0.0331 (9)
H14	−0.0332	1.0856	0.1873	0.040*
C26	0.36606 (17)	0.6671 (3)	−0.1501 (3)	0.0300 (9)
H26	0.3885	0.6732	−0.2076	0.036*
C3	0.42037 (19)	0.1600 (3)	0.5282 (3)	0.0381 (10)
H3	0.4446	0.0903	0.5733	0.046*
O3	0.45503 (12)	0.6073 (3)	0.2347 (2)	0.0496 (7)
H3A	0.4200	0.5690	0.2430	0.074*
C31	0.51281 (18)	0.5443 (4)	0.3014 (4)	0.0487 (11)
H31A	0.5537	0.5877	0.2906	0.073*
H31B	0.5128	0.4494	0.2810	0.073*
H31C	0.5122	0.5518	0.3792	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0281 (2)	0.0251 (2)	0.0184 (2)	0.0030 (2)	0.00950 (17)	0.0013 (2)
N2	0.0245 (14)	0.0205 (15)	0.0193 (15)	0.0015 (13)	0.0081 (12)	0.0036 (13)
N4	0.0260 (15)	0.0254 (16)	0.0228 (17)	0.0045 (13)	0.0087 (13)	0.0020 (13)
O1	0.0274 (12)	0.0288 (13)	0.0199 (14)	0.0057 (10)	0.0090 (11)	0.0031 (10)
O2	0.0360 (13)	0.0264 (13)	0.0220 (14)	0.0046 (11)	0.0124 (11)	0.0042 (10)
N1	0.0271 (16)	0.0227 (15)	0.0187 (16)	0.0027 (12)	0.0079 (13)	0.0015 (13)
C22	0.0337 (19)	0.0243 (19)	0.024 (2)	0.0075 (18)	0.0038 (16)	0.0030 (17)
C10	0.0194 (16)	0.0169 (17)	0.0224 (19)	−0.0027 (14)	0.0026 (14)	−0.0041 (15)
C30	0.0228 (18)	0.0262 (19)	0.0174 (19)	0.0095 (15)	0.0065 (16)	0.0066 (15)
C18	0.0289 (19)	0.0201 (19)	0.0185 (19)	−0.0016 (14)	0.0032 (16)	−0.0031 (14)
C17	0.036 (2)	0.026 (2)	0.022 (2)	−0.0012 (16)	0.0056 (18)	0.0032 (16)
C19	0.034 (2)	0.031 (2)	0.036 (2)	0.0011 (19)	0.0110 (18)	0.0088 (19)
C29	0.0224 (18)	0.0227 (19)	0.022 (2)	0.0086 (15)	0.0055 (16)	0.0038 (15)
N3	0.0268 (16)	0.0256 (16)	0.0210 (17)	0.0045 (13)	0.0104 (14)	0.0041 (12)
C28	0.032 (2)	0.033 (2)	0.026 (2)	0.0006 (17)	0.0095 (17)	0.0021 (17)
C7	0.0259 (19)	0.0244 (19)	0.0153 (19)	−0.0037 (15)	0.0059 (16)	−0.0025 (14)
C6	0.0232 (17)	0.0203 (17)	0.0228 (19)	−0.0037 (16)	0.0041 (15)	−0.0006 (16)
C5	0.0295 (19)	0.0247 (19)	0.031 (2)	0.0005 (16)	0.0073 (17)	−0.0022 (16)
C8	0.0247 (18)	0.0218 (18)	0.0187 (19)	−0.0035 (15)	0.0089 (16)	−0.0026 (15)
C15	0.0241 (19)	0.0218 (19)	0.030 (2)	0.0010 (15)	0.0062 (17)	−0.0016 (16)
C27	0.029 (2)	0.040 (2)	0.032 (2)	0.0010 (17)	0.0136 (18)	0.0117 (18)
C25	0.0258 (19)	0.0297 (19)	0.021 (2)	0.0111 (16)	0.0067 (17)	0.0051 (16)
C9	0.0244 (18)	0.0197 (18)	0.0193 (19)	−0.0012 (15)	0.0050 (15)	−0.0006 (15)
C24	0.042 (2)	0.041 (2)	0.022 (2)	0.0164 (19)	0.0154 (19)	0.0033 (17)
C16	0.0294 (19)	0.0234 (19)	0.032 (2)	0.0071 (16)	0.0024 (18)	0.0030 (16)
C4	0.032 (2)	0.030 (2)	0.037 (2)	0.0038 (17)	0.0012 (19)	−0.0067 (18)
C23	0.047 (2)	0.034 (2)	0.021 (2)	0.008 (2)	0.0072 (18)	−0.0025 (18)
C12	0.032 (2)	0.033 (2)	0.036 (2)	−0.0023 (18)	0.0159 (18)	−0.0052 (18)
C20	0.040 (2)	0.026 (2)	0.045 (3)	−0.0039 (18)	0.007 (2)	0.0040 (19)
C21	0.039 (2)	0.028 (2)	0.033 (2)	0.0024 (18)	0.0009 (19)	−0.0030 (17)
C13	0.029 (2)	0.032 (2)	0.048 (3)	0.0073 (18)	0.016 (2)	−0.0036 (19)
C11	0.0256 (18)	0.0216 (19)	0.029 (2)	0.0011 (15)	0.0090 (17)	0.0004 (15)
C2	0.037 (2)	0.033 (2)	0.026 (2)	−0.0103 (18)	−0.0001 (18)	0.0073 (17)
C1	0.0255 (19)	0.032 (2)	0.023 (2)	−0.0059 (16)	0.0034 (17)	−0.0017 (16)
C14	0.028 (2)	0.027 (2)	0.041 (3)	0.0077 (16)	0.0046 (19)	0.0043 (17)
C26	0.029 (2)	0.040 (2)	0.025 (2)	0.0100 (17)	0.0146 (18)	0.0105 (17)
C3	0.041 (2)	0.027 (2)	0.037 (2)	0.0005 (17)	−0.008 (2)	0.0085 (17)
O3	0.0353 (15)	0.0576 (19)	0.057 (2)	−0.0004 (15)	0.0143 (15)	0.0074 (15)
C31	0.035 (2)	0.056 (3)	0.056 (3)	−0.007 (2)	0.014 (2)	−0.009 (2)

Geometric parameters (Å, º) top

Cu1—O2	1.913 (2)	C8—C9	1.437 (4)
Cu1—N2	1.914 (2)	C8—H8	0.9500
Cu1—O1	1.984 (2)	C15—C14	1.405 (4)
Cu1—N4	2.023 (3)	C15—C16	1.417 (5)
Cu1—N3	2.321 (3)	C27—C26	1.357 (5)
N2—C8	1.296 (4)	C27—H27	0.9500
N2—N1	1.396 (3)	C25—C26	1.408 (4)
N4—C28	1.328 (4)	C25—C24	1.427 (5)
N4—C30	1.360 (4)	C24—C23	1.344 (4)
O1—C7	1.312 (4)	C24—H24	0.9500
O2—C18	1.306 (3)	C16—H16	0.9500
N1—C7	1.315 (4)	C4—C3	1.384 (5)
C22—C21	1.395 (4)	C4—H4	0.9500
C22—C29	1.406 (4)	C23—H23	0.9500
C22—C23	1.431 (4)	C12—C11	1.374 (4)
C10—C11	1.416 (4)	C12—C13	1.395 (5)
C10—C15	1.416 (4)	C12—H12	0.9500
C10—C9	1.454 (4)	C20—C21	1.367 (5)
C30—C25	1.407 (4)	C20—H20	0.9500
C30—C29	1.436 (4)	C21—H21	0.9500
C18—C9	1.416 (4)	C13—C14	1.362 (5)
C18—C17	1.433 (4)	C13—H13	0.9500
C17—C16	1.349 (4)	C11—H11	0.9500
C17—H17	0.9500	C2—C1	1.378 (4)
C19—N3	1.323 (4)	C2—C3	1.382 (5)
C19—C20	1.400 (5)	C2—H2	0.9500
C19—H19	0.9500	C1—H1	0.9500
C29—N3	1.352 (4)	C14—H14	0.9500
C28—C27	1.390 (4)	C26—H26	0.9500
C28—H28	0.9500	C3—H3	0.9500
C7—C6	1.480 (4)	O3—C31	1.403 (4)
C6—C5	1.387 (4)	O3—H3A	0.8400
C6—C1	1.396 (4)	C31—H31A	0.9800
C5—C4	1.388 (5)	C31—H31B	0.9800
C5—H5	0.9500	C31—H31C	0.9800

O2—Cu1—N2	91.80 (10)	C10—C15—C16	118.3 (3)
O2—Cu1—O1	162.81 (9)	C26—C27—C28	118.9 (3)
N2—Cu1—O1	80.85 (10)	C26—C27—H27	120.6
O2—Cu1—N4	90.39 (10)	C28—C27—H27	120.6
N2—Cu1—N4	172.79 (11)	C30—C25—C26	117.6 (3)
O1—Cu1—N4	95.16 (9)	C30—C25—C24	118.9 (3)
O2—Cu1—N3	101.75 (9)	C26—C25—C24	123.5 (3)
N2—Cu1—N3	109.43 (10)	C18—C9—C8	121.6 (3)
O1—Cu1—N3	95.36 (9)	C18—C9—C10	119.0 (3)
N4—Cu1—N3	76.80 (10)	C8—C9—C10	119.4 (3)
C8—N2—N1	115.4 (3)	C23—C24—C25	121.5 (3)
C8—N2—Cu1	128.7 (2)	C23—C24—H24	119.3
N1—N2—Cu1	115.65 (18)	C25—C24—H24	119.3
C28—N4—C30	118.9 (3)	C17—C16—C15	122.2 (3)
C28—N4—Cu1	123.1 (2)	C17—C16—H16	118.9
C30—N4—Cu1	118.0 (2)	C15—C16—H16	118.9
C7—O1—Cu1	109.05 (19)	C3—C4—C5	119.9 (3)
C18—O2—Cu1	127.8 (2)	C3—C4—H4	120.1
C7—N1—N2	109.5 (2)	C5—C4—H4	120.1
C21—C22—C29	117.3 (3)	C24—C23—C22	121.1 (3)
C21—C22—C23	123.5 (3)	C24—C23—H23	119.4
C29—C22—C23	119.2 (3)	C22—C23—H23	119.4
C11—C10—C15	116.7 (3)	C11—C12—C13	121.0 (3)
C11—C10—C9	123.3 (3)	C11—C12—H12	119.5
C15—C10—C9	120.0 (3)	C13—C12—H12	119.5
N4—C30—C25	121.4 (3)	C21—C20—C19	118.8 (3)
N4—C30—C29	118.7 (3)	C21—C20—H20	120.6
C25—C30—C29	119.9 (3)	C19—C20—H20	120.6
O2—C18—C9	125.3 (3)	C20—C21—C22	119.7 (3)
O2—C18—C17	116.0 (3)	C20—C21—H21	120.2
C9—C18—C17	118.6 (3)	C22—C21—H21	120.2
C16—C17—C18	121.4 (3)	C14—C13—C12	118.9 (3)
C16—C17—H17	119.3	C14—C13—H13	120.5
C18—C17—H17	119.3	C12—C13—H13	120.5
N3—C19—C20	123.6 (3)	C12—C11—C10	121.4 (3)
N3—C19—H19	118.2	C12—C11—H11	119.3
C20—C19—H19	118.2	C10—C11—H11	119.3
N3—C29—C22	123.3 (3)	C1—C2—C3	120.7 (3)
N3—C29—C30	117.2 (3)	C1—C2—H2	119.7
C22—C29—C30	119.5 (3)	C3—C2—H2	119.7
C19—N3—C29	117.3 (3)	C2—C1—C6	120.5 (3)
C19—N3—Cu1	133.5 (2)	C2—C1—H1	119.8
C29—N3—Cu1	109.2 (2)	C6—C1—H1	119.8
N4—C28—C27	123.0 (3)	C13—C14—C15	121.6 (3)
N4—C28—H28	118.5	C13—C14—H14	119.2
C27—C28—H28	118.5	C15—C14—H14	119.2
O1—C7—N1	124.2 (3)	C27—C26—C25	120.2 (3)
O1—C7—C6	118.8 (3)	C27—C26—H26	119.9
N1—C7—C6	117.0 (3)	C25—C26—H26	119.9
C5—C6—C1	118.5 (3)	C2—C3—C4	119.5 (3)
C5—C6—C7	120.8 (3)	C2—C3—H3	120.2
C1—C6—C7	120.7 (3)	C4—C3—H3	120.2
C6—C5—C4	121.0 (3)	C31—O3—H3A	109.5
C6—C5—H5	119.5	O3—C31—H31A	109.5
C4—C5—H5	119.5	O3—C31—H31B	109.5
N2—C8—C9	124.3 (3)	H31A—C31—H31B	109.5
N2—C8—H8	117.9	O3—C31—H31C	109.5
C9—C8—H8	117.9	H31A—C31—H31C	109.5
C14—C15—C10	120.2 (3)	H31B—C31—H31C	109.5
C14—C15—C16	121.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1	0.84	1.99	2.820 (3)	167

Experimental details

Crystal data
Chemical formula	[Cu(C₁₈H₁₂N₂O₂)(C₁₂H₈N₂)]·CH₄O
M_r	564.08
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	185
a, b, c (Å)	20.388 (2), 9.9707 (10), 12.5268 (12)
β (°)	105.035 (2)
V (Å³)	2459.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.93
Crystal size (mm)	0.20 × 0.18 × 0.17

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.836, 0.858
No. of measured, independent and observed [I > 2σ(I)] reflections	12077, 4352, 2950
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.093, 1.02
No. of reflections	4352
No. of parameters	354
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.32

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Cu1—O2	1.913 (2)	Cu1—N4	2.023 (3)
Cu1—N2	1.914 (2)	Cu1—N3	2.321 (3)
Cu1—O1	1.984 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1	0.84	1.99	2.820 (3)	167.1

Acknowledgements

The authors thank the Natural Science Foundation of Jilin University.

References

Anford, J. D., Vittal, J. J. & Wang, Y. M. (1998). Inorg. Chem. 37, 1226–1231. Web of Science CSD CrossRef PubMed Google Scholar
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Guo, Y.-N., Xu, G.-F., Gamez, P., Zhao, L., Lin, S.-Y., Deng, R., Tang, J.-K. & Zhang, H.-J. (2010). J. Am. Chem. Soc. 132, 8538–8539. Web of Science CSD CrossRef CAS PubMed Google Scholar
Huo, L.-H., Lu, Z.-Z., Gao, S., Zhao, H. & Zhao, J.-G. (2004). Acta Cryst. E60, m1636–m1638. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, H.-Y., Lu, Z.-S. & Niu, D.-Z. (2008). J. Coord. Chem. 61, 4040–4046. Web of Science CSD CrossRef CAS Google Scholar
Qiao, Y., Ju, X., Gao, Z. & Kong, L. (2010). Acta Cryst. E66, o95. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sreeja, P. B., Prathapachandra Kurup, M. R., Kishore, A. & Jasmin, C. (2004). Polyhedron. 23, 575–581. Web of Science CSD CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 1| January 2012| Page m86

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

{N′-[(2-Oxidonaphthalen-1-yl)methyl­­idene]benzohydrazidato}(1,10-phenanthroline)copper(II) methanol monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

{N′-[(2-Oxidonaphthalen-1-yl)methylidene]benzohydrazidato}(1,10-phenanthroline)copper(II) methanol monosolvate