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

The title mononuclear complex, [Cu(C(18)H(12)N(2)O(2))(C(12)H(8)N(2))]·CH(3)OH, contains one N'-[(2-oxidonaphthalen-1-yl)methyl-idene]benzohydrazidate ligand (L(2-)), a Cu(2+) cation, one 1,10-phenanthroline ligand and a methanol solvent mol-ecule. The Cu(II) ion adopts a CuO(2)N(3) distorted square-pyramidal coordination. An O-H⋯O hydrogen bond is formed between the methanol solvent mol-ecule and the hydrazide O atom of the L(2-) 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 = 564.08

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.093

S = 1.02

4352 reflections

354 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.32 e Å−3

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) ▶.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811054316/kp2374sup1.cif

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

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

[Cu(C18H12N2O2)(C12H8N2)]·CH4O	F(000) = 1164
Mr = 564.08	Dx = 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

Bruker APEXII CCD area-detector diffractometer	4352 independent reflections
Radiation source: fine-focus sealed tube	2950 reflections with I > 2σ(I)
graphite	Rint = 0.059
phi and ω scans	θmax = 25.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −21→24
Tmin = 0.836, Tmax = 0.858	k = −11→10
12077 measured reflections	l = −14→12

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(Fo2) + (0.0369P)2 + 0.1098P] where P = (Fo2 + 2Fc2)/3
4352 reflections	(Δ/σ)max < 0.001
354 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.32 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	0.25702 (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*

	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)

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)

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

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