{2-(4-Hy-droxy-phen-yl)-2-[(3-meth-oxy-2-oxidobenzyl-idene)amino-κO,N]propanoato-κO}(1,10-phenanthroline-κN,N')copper(II) dihydrate.

In the title complex, [Cu(C(17)H(15)NO(5))(C(12)H(8)N(2))]·2H(2)O, the central Cu(II) ion is five-coordinate, bound to one N atom and two O atoms from the Schiff base ligand and by two N atoms from a 1,10-phenanthroline ligand in a distorted square-pyramidal configuration. In the crystal, inter-molecular O-H⋯O and C-H⋯O hydrogen bonds form a two-dimensional network parallel to (001).

Related literature

For background to Schiff bases and the applications of Schiff base–copper complexes, see: Chohan et al. (1998 ▶); Nath et al. (2001 ▶); Raso et al. (1999 ▶); Yamada (1966 ▶). For the structure of a similar complex with a five-coordinate CuII ion, see: Qiu et al. (2008 ▶).

Experimental

Crystal data

[Cu(C17H15NO5)(C12H8N2)]·2H2O

M = 593.08

Monoclinic,

a = 11.755 (3) Å

b = 20.653 (5) Å

c = 13.202 (3) Å

β = 96.935 (4)°

V = 3181.6 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.73 mm−1

T = 298 K

0.48 × 0.42 × 0.38 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.720, T max = 0.769

8117 measured reflections

3778 independent reflections

2811 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.202

S = 1.04

3778 reflections

363 parameters

15 restraints

H-atom parameters constrained

Δρmax = 1.19 e Å−3

Δρmin = −0.32 e Å−3

Absolute structure: Flack (1983 ▶), 956 Friedel pairs

Flack parameter: −0.02 (3)

Data collection: SMART (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: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811009627/rn2083sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009627/rn2083Isup2.hkl

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

[Cu(C17H15NO5)(C12H8N2)]·2H2O	F(000) = 1228
Mr = 593.08	Dx = 1.238 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 2405 reflections
a = 11.755 (3) Å	θ = 2.4–22.2°
b = 20.653 (5) Å	µ = 0.73 mm−1
c = 13.202 (3) Å	T = 298 K
β = 96.935 (4)°	Block, blue
V = 3181.6 (14) Å3	0.48 × 0.42 × 0.38 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	3778 independent reflections
Radiation source: fine-focus sealed tube	2811 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.720, Tmax = 0.769	k = −10→24
8117 measured reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.071	H-atom parameters constrained
wR(F2) = 0.202	w = 1/[σ2(Fo2) + (0.1348P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3778 reflections	Δρmax = 1.19 e Å−3
363 parameters	Δρmin = −0.32 e Å−3
15 restraints	Absolute structure: Flack (1983), 957 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.02 (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	0.47884 (7)	0.39140 (5)	0.30240 (6)	0.0528 (3)
O1	0.3247 (4)	0.3954 (4)	0.2218 (4)	0.0629 (13)
O2	0.1982 (6)	0.4622 (4)	0.1409 (6)	0.086 (2)
O3	0.6863 (7)	0.7563 (4)	0.1644 (6)	0.093 (2)
H3	0.6884	0.7738	0.1089	0.139*
O4	0.6105 (4)	0.3954 (4)	0.4054 (4)	0.0615 (13)
O5	0.7833 (6)	0.3774 (4)	0.5400 (5)	0.085 (2)
O6	0.0460 (5)	0.3655 (3)	0.1065 (5)	0.091 (2)
H30	0.0785	0.3555	0.0545	0.110*
H31	0.0698	0.4039	0.1183	0.110*
O7	0.1122 (9)	0.5336 (6)	0.9760 (9)	0.140 (4)
H33	0.1504	0.5389	1.0343	0.169*
H32	0.1276	0.4940	0.9671	0.169*
N1	0.4673 (6)	0.4843 (5)	0.2928 (5)	0.048 (2)
N3	0.4572 (7)	0.2951 (4)	0.3234 (6)	0.057 (2)
N2	0.5696 (6)	0.3454 (4)	0.1729 (5)	0.064 (2)
C1	0.2914 (8)	0.4502 (5)	0.1928 (7)	0.064 (2)
C2	0.3727 (7)	0.5070 (4)	0.2167 (6)	0.0523 (19)
H2	0.3323	0.5430	0.2447	0.063*
C3	0.4188 (7)	0.5280 (5)	0.1168 (6)	0.058 (2)
H3A	0.4647	0.4932	0.0938	0.070*
H3B	0.3544	0.5350	0.0647	0.070*
C4	0.4896 (7)	0.5882 (4)	0.1279 (5)	0.0502 (18)
C5	0.4378 (8)	0.6477 (5)	0.1252 (8)	0.072 (3)
H5	0.3583	0.6500	0.1152	0.086*
C6	0.5015 (8)	0.7054 (5)	0.1372 (7)	0.070 (2)
H6	0.4648	0.7453	0.1353	0.084*
C7	0.6210 (9)	0.7016 (5)	0.1519 (6)	0.067 (2)
C8	0.6746 (8)	0.6425 (6)	0.1572 (7)	0.070 (3)
H8	0.7542	0.6405	0.1691	0.084*
C9	0.6109 (8)	0.5849 (5)	0.1449 (6)	0.059 (2)
H9	0.6479	0.5451	0.1479	0.071*
C10	0.5227 (7)	0.5261 (5)	0.3509 (6)	0.055 (2)
H10	0.5003	0.5692	0.3433	0.065*
C11	0.6173 (7)	0.5113 (5)	0.4271 (6)	0.055 (2)
C12	0.6726 (9)	0.5654 (5)	0.4794 (7)	0.075 (3)
H12	0.6470	0.6075	0.4654	0.090*
C13	0.7641 (9)	0.5534 (7)	0.5505 (8)	0.089 (3)
H13	0.8008	0.5880	0.5857	0.107*
C14	0.8038 (10)	0.4923 (6)	0.5719 (7)	0.079 (3)
H14	0.8680	0.4864	0.6194	0.095*
C15	0.7517 (8)	0.4403 (6)	0.5254 (6)	0.061 (2)
C16	0.6550 (7)	0.4463 (5)	0.4466 (6)	0.056 (2)
C17	0.8766 (10)	0.3668 (7)	0.6178 (10)	0.106 (4)
H17A	0.9476	0.3727	0.5899	0.158*
H17B	0.8728	0.3235	0.6435	0.158*
H17C	0.8722	0.3971	0.6723	0.158*
C18	0.4013 (8)	0.2711 (5)	0.3963 (7)	0.068 (2)
H18	0.3718	0.2998	0.4408	0.081*
C19	0.3855 (10)	0.2077 (6)	0.4090 (9)	0.084 (3)
H19	0.3461	0.1933	0.4617	0.101*
C20	0.4272 (10)	0.1631 (6)	0.3443 (10)	0.085 (3)
H20	0.4154	0.1189	0.3515	0.101*
C21	0.4880 (8)	0.1874 (5)	0.2676 (8)	0.067 (2)
C22	0.5018 (7)	0.2544 (5)	0.2576 (7)	0.059 (2)
C23	0.5601 (7)	0.2798 (5)	0.1781 (6)	0.054 (2)
C24	0.6054 (9)	0.2391 (6)	0.1102 (8)	0.073 (3)
C25	0.6605 (8)	0.2653 (7)	0.0366 (8)	0.088 (3)
H25	0.6918	0.2384	−0.0093	0.106*
C26	0.6710 (10)	0.3290 (8)	0.0287 (9)	0.092 (3)
H26	0.7081	0.3465	−0.0233	0.110*
C27	0.6258 (8)	0.3701 (6)	0.0993 (7)	0.080 (3)
H27	0.6350	0.4147	0.0948	0.096*
C28	0.5357 (9)	0.1457 (6)	0.1986 (10)	0.085 (3)
H28	0.5291	0.1010	0.2037	0.103*
C29	0.5923 (12)	0.1733 (7)	0.1232 (10)	0.092 (4)
H29	0.6236	0.1457	0.0783	0.110*

	U11	U22	U33	U12	U13	U23
Cu1	0.0548 (5)	0.0557 (6)	0.0464 (5)	−0.0062 (6)	−0.0006 (3)	0.0017 (5)
O1	0.062 (3)	0.053 (3)	0.070 (3)	−0.016 (4)	−0.005 (2)	0.000 (4)
O2	0.070 (4)	0.092 (5)	0.089 (5)	−0.018 (4)	−0.025 (4)	0.032 (4)
O3	0.096 (5)	0.082 (5)	0.102 (5)	−0.038 (4)	0.023 (4)	−0.002 (4)
O4	0.066 (3)	0.059 (3)	0.055 (3)	−0.004 (4)	−0.009 (2)	−0.001 (4)
O5	0.086 (4)	0.090 (7)	0.072 (4)	0.003 (4)	−0.021 (3)	0.009 (4)
O6	0.108 (5)	0.077 (5)	0.084 (5)	−0.032 (4)	−0.008 (4)	0.007 (4)
O7	0.127 (7)	0.129 (9)	0.162 (9)	0.001 (7)	0.002 (6)	0.026 (8)
N1	0.052 (4)	0.054 (5)	0.037 (3)	−0.001 (3)	0.003 (3)	0.003 (3)
N3	0.057 (4)	0.056 (5)	0.057 (4)	−0.004 (4)	0.001 (3)	−0.005 (4)
N2	0.053 (4)	0.084 (6)	0.052 (4)	−0.003 (4)	−0.006 (3)	−0.002 (4)
C1	0.055 (5)	0.063 (6)	0.071 (5)	−0.014 (4)	−0.004 (4)	0.009 (5)
C2	0.056 (4)	0.056 (5)	0.044 (4)	0.000 (4)	0.001 (3)	0.007 (4)
C3	0.055 (4)	0.073 (6)	0.046 (4)	−0.013 (4)	0.002 (3)	0.005 (4)
C4	0.060 (5)	0.051 (5)	0.039 (4)	−0.008 (4)	0.004 (3)	0.006 (3)
C5	0.053 (5)	0.073 (7)	0.092 (7)	0.009 (5)	0.019 (4)	0.020 (6)
C6	0.074 (6)	0.057 (6)	0.082 (6)	−0.003 (5)	0.020 (5)	0.006 (5)
C7	0.089 (6)	0.062 (6)	0.054 (5)	−0.014 (5)	0.021 (4)	0.000 (4)
C8	0.051 (5)	0.083 (7)	0.071 (6)	−0.021 (5)	−0.012 (4)	0.007 (5)
C9	0.067 (5)	0.064 (6)	0.047 (5)	−0.004 (5)	0.005 (4)	0.001 (4)
C10	0.062 (5)	0.054 (5)	0.044 (4)	−0.014 (4)	−0.005 (4)	0.001 (4)
C11	0.056 (4)	0.062 (6)	0.047 (4)	−0.009 (4)	0.008 (3)	−0.002 (4)
C12	0.097 (7)	0.066 (6)	0.058 (5)	−0.014 (6)	−0.005 (5)	−0.010 (5)
C13	0.086 (7)	0.099 (9)	0.076 (7)	−0.021 (6)	−0.016 (5)	−0.018 (6)
C14	0.088 (7)	0.094 (8)	0.051 (5)	−0.015 (6)	−0.006 (5)	0.000 (5)
C15	0.057 (5)	0.081 (7)	0.043 (4)	−0.005 (5)	0.000 (3)	0.011 (5)
C16	0.053 (4)	0.075 (6)	0.039 (4)	−0.006 (4)	0.001 (3)	−0.002 (4)
C17	0.088 (7)	0.126 (12)	0.090 (7)	0.011 (7)	−0.037 (6)	−0.001 (7)
C18	0.069 (5)	0.076 (7)	0.059 (5)	−0.006 (5)	0.014 (4)	0.005 (5)
C19	0.088 (7)	0.083 (8)	0.083 (7)	−0.026 (6)	0.018 (5)	0.003 (6)
C20	0.088 (7)	0.061 (6)	0.101 (8)	−0.016 (6)	−0.004 (6)	−0.007 (6)
C21	0.067 (5)	0.050 (5)	0.077 (6)	−0.006 (5)	−0.016 (4)	−0.005 (5)
C22	0.053 (4)	0.063 (6)	0.054 (5)	−0.008 (4)	−0.017 (4)	−0.003 (4)
C23	0.049 (4)	0.062 (6)	0.047 (4)	0.001 (4)	−0.003 (3)	−0.008 (4)
C24	0.067 (6)	0.085 (7)	0.063 (5)	0.005 (5)	−0.007 (4)	−0.016 (5)
C25	0.066 (6)	0.121 (8)	0.075 (6)	0.022 (7)	0.001 (5)	−0.012 (7)
C26	0.081 (7)	0.132 (9)	0.066 (6)	0.025 (7)	0.022 (5)	0.015 (7)
C27	0.076 (5)	0.105 (10)	0.060 (5)	0.001 (6)	0.013 (4)	0.015 (6)
C28	0.083 (7)	0.061 (7)	0.108 (9)	−0.005 (5)	−0.006 (6)	−0.005 (6)
C29	0.092 (8)	0.092 (8)	0.088 (8)	0.012 (7)	−0.001 (6)	−0.041 (7)

Cu1—N1	1.926 (10)	C8—H8	0.9300
Cu1—O4	1.935 (5)	C9—H9	0.9300
Cu1—O1	1.989 (5)	C10—C11	1.439 (11)
Cu1—N3	2.029 (9)	C10—H10	0.9300
Cu1—N2	2.325 (8)	C11—C12	1.429 (13)
O1—C1	1.243 (12)	C11—C16	1.428 (13)
O2—C1	1.245 (11)	C12—C13	1.363 (15)
O3—C7	1.365 (12)	C12—H12	0.9300
O3—H3	0.8200	C13—C14	1.363 (17)
O4—C16	1.267 (12)	C13—H13	0.9300
O5—C15	1.357 (14)	C14—C15	1.347 (15)
O5—C17	1.425 (12)	C14—H14	0.9300
O6—H30	0.8500	C15—C16	1.450 (12)
O6—H31	0.8500	C17—H17A	0.9600
O7—H33	0.8500	C17—H17B	0.9600
O7—H32	0.8501	C17—H17C	0.9600
N1—C10	1.280 (11)	C18—C19	1.337 (16)
N1—C2	1.482 (10)	C18—H18	0.9300
N3—C18	1.325 (13)	C19—C20	1.384 (17)
N3—C22	1.358 (13)	C19—H19	0.9300
N2—C27	1.339 (12)	C20—C21	1.400 (17)
N2—C23	1.361 (12)	C20—H20	0.9300
C1—C2	1.521 (12)	C21—C22	1.402 (14)
C2—C3	1.547 (11)	C21—C28	1.418 (16)
C2—H2	0.9800	C22—C23	1.422 (13)
C3—C4	1.493 (12)	C23—C24	1.382 (14)
C3—H3A	0.9700	C24—C25	1.346 (16)
C3—H3B	0.9700	C24—C29	1.379 (18)
C4—C5	1.370 (13)	C25—C26	1.327 (19)
C4—C9	1.418 (13)	C25—H25	0.9300
C5—C6	1.405 (14)	C26—C27	1.412 (17)
C5—H5	0.9300	C26—H26	0.9300
C6—C7	1.396 (14)	C27—H27	0.9300
C6—H6	0.9300	C28—C29	1.39 (2)
C7—C8	1.373 (15)	C28—H28	0.9300
C8—C9	1.404 (14)	C29—H29	0.9300
N1—Cu1—O4	92.8 (3)	C12—C11—C16	122.4 (8)
N1—Cu1—O1	82.6 (3)	C12—C11—C10	116.1 (9)
O4—Cu1—O1	166.9 (3)	C16—C11—C10	121.5 (8)
N1—Cu1—N3	167.6 (3)	C13—C12—C11	117.7 (10)
O4—Cu1—N3	92.8 (3)	C13—C12—H12	121.1
O1—Cu1—N3	89.6 (3)	C11—C12—H12	121.1
N1—Cu1—N2	113.2 (3)	C14—C13—C12	122.3 (11)
O4—Cu1—N2	97.8 (2)	C14—C13—H13	118.9
O1—Cu1—N2	95.3 (2)	C12—C13—H13	118.9
N3—Cu1—N2	77.1 (3)	C15—C14—C13	121.2 (10)
C1—O1—Cu1	115.8 (6)	C15—C14—H14	119.4
C7—O3—H3	109.5	C13—C14—H14	119.4
C16—O4—Cu1	126.2 (7)	C14—C15—O5	126.5 (8)
C15—O5—C17	115.1 (9)	C14—C15—C16	122.2 (10)
H30—O6—H31	101.8	O5—C15—C16	111.2 (9)
H33—O7—H32	98.7	O4—C16—C11	126.9 (7)
C10—N1—C2	118.6 (9)	O4—C16—C15	118.9 (9)
C10—N1—Cu1	127.3 (6)	C11—C16—C15	114.2 (8)
C2—N1—Cu1	113.6 (6)	O5—C17—H17A	109.5
C18—N3—C22	119.8 (9)	O5—C17—H17B	109.5
C18—N3—Cu1	123.1 (8)	H17A—C17—H17B	109.5
C22—N3—Cu1	117.1 (7)	O5—C17—H17C	109.5
C27—N2—C23	117.8 (9)	H17A—C17—H17C	109.5
C27—N2—Cu1	133.5 (7)	H17B—C17—H17C	109.5
C23—N2—Cu1	108.7 (6)	N3—C18—C19	123.1 (10)
O1—C1—O2	125.1 (9)	N3—C18—H18	118.5
O1—C1—C2	118.1 (7)	C19—C18—H18	118.5
O2—C1—C2	116.7 (9)	C18—C19—C20	120.6 (10)
N1—C2—C1	107.4 (7)	C18—C19—H19	119.7
N1—C2—C3	110.8 (6)	C20—C19—H19	119.7
C1—C2—C3	108.4 (7)	C19—C20—C21	117.3 (10)
N1—C2—H2	110.1	C19—C20—H20	121.4
C1—C2—H2	110.1	C21—C20—H20	121.4
C3—C2—H2	110.1	C22—C21—C20	119.8 (10)
C4—C3—C2	113.5 (7)	C22—C21—C28	118.6 (10)
C4—C3—H3A	108.9	C20—C21—C28	121.6 (10)
C2—C3—H3A	108.9	N3—C22—C21	119.5 (9)
C4—C3—H3B	108.9	N3—C22—C23	120.1 (9)
C2—C3—H3B	108.9	C21—C22—C23	120.4 (9)
H3A—C3—H3B	107.7	N2—C23—C24	122.2 (9)
C5—C4—C9	118.8 (8)	N2—C23—C22	117.1 (8)
C5—C4—C3	120.2 (8)	C24—C23—C22	120.7 (10)
C9—C4—C3	121.0 (8)	C25—C24—C23	118.7 (12)
C4—C5—C6	121.9 (8)	C25—C24—C29	123.8 (12)
C4—C5—H5	119.1	C23—C24—C29	117.5 (11)
C6—C5—H5	119.1	C26—C25—C24	120.9 (12)
C7—C6—C5	118.8 (9)	C26—C25—H25	119.5
C7—C6—H6	120.6	C24—C25—H25	119.5
C5—C6—H6	120.6	C25—C26—C27	119.9 (11)
O3—C7—C8	118.8 (9)	C25—C26—H26	120.1
O3—C7—C6	120.9 (10)	C27—C26—H26	120.1
C8—C7—C6	120.3 (9)	N2—C27—C26	120.6 (12)
C7—C8—C9	120.8 (9)	N2—C27—H27	119.7
C7—C8—H8	119.6	C26—C27—H27	119.7
C9—C8—H8	119.6	C29—C28—C21	118.2 (11)
C8—C9—C4	119.4 (10)	C29—C28—H28	120.9
C8—C9—H9	120.3	C21—C28—H28	120.9
C4—C9—H9	120.3	C24—C29—C28	124.4 (12)
N1—C10—C11	124.7 (9)	C24—C29—H29	117.8
N1—C10—H10	117.6	C28—C29—H29	117.8
C11—C10—H10	117.6
C1—C2—C3—C4	173.6 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H31···O2	0.85	1.93	2.684 (9)	148
O3—H3···O6i	0.82	2.53	2.843 (11)	104
O6—H30···O6ii	0.85	2.44	2.888 (11)	114
O7—H33···O2iii	0.85	2.15	2.721 (13)	125
C18—H18···O5iv	0.93	2.46	3.268 (13)	145

Table 1

Selected bond lengths (Å)

Cu1—N1	1.926 (10)
Cu1—O4	1.935 (5)
Cu1—O1	1.989 (5)
Cu1—N3	2.029 (9)
Cu1—N2	2.325 (8)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H31⋯O2	0.85	1.93	2.684 (9)	148
O3—H3⋯O6i	0.82	2.53	2.843 (11)	104
O6—H30⋯O6ii	0.85	2.44	2.888 (11)	114
O7—H33⋯O2iii	0.85	2.15	2.721 (13)	125
C18—H18⋯O5iv	0.93	2.46	3.268 (13)	145

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