{N-[(2-Oxido-1-naphth-yl)methyl-idene]-serinato-κO,N,O'}(1,10-phenanthroline-κN,N')copper(II).

In the title complex, [Cu(C(14)H(11)NO(4))(C(12)H(8)N(2))], the tridentate Schiff base ligand is derived from the condensation of 2-hydr-oxy-1-naphthaldehyde and l-serine. The Cu(II) atom is five-coordinated by 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 geometry. In the crystal structure, the combination of inter-molecular O-H⋯O and C-H⋯O hydrogen bonds results in a two-dimensional network structure parallel to (001).

Related literature

For general background to Schiff base complexes, see: Garnovski et al. (1993 ▶); Kalagouda et al. (2006 ▶); Wang et al. (1999 ▶). For our previous work on amino Schiff base complexes, see: Qiu et al. (2008 ▶); Wang et al. (2007 ▶).

Experimental

Crystal data

[Cu(C14H11NO4)(C12H8N2)]

M = 500.98

Monoclinic,

a = 10.7302 (12) Å

b = 6.4687 (6) Å

c = 15.7930 (17) Å

β = 91.924 (1)°

V = 1095.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.04 mm−1

T = 298 K

0.43 × 0.16 × 0.08 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.664, T max = 0.922

5555 measured reflections

3633 independent reflections

3022 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.094

S = 0.97

3633 reflections

307 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), with 1529 Friedel pairs

Flack parameter: −0.023 (17)

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/S1600536810012675/hy2297sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012675/hy2297Isup2.hkl

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

[Cu(C14H11NO4)(C12H8N2)]	F(000) = 514
Mr = 500.98	Dx = 1.519 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 746 reflections
a = 10.7302 (12) Å	θ = 3.3–25.2°
b = 6.4687 (6) Å	µ = 1.04 mm−1
c = 15.7930 (17) Å	T = 298 K
β = 91.924 (1)°	Needle, green
V = 1095.6 (2) Å3	0.43 × 0.16 × 0.08 mm
Z = 2

Bruker SMART 1000 CCD area-detector diffractometer	3633 independent reflections
Radiation source: fine-focus sealed tube	3022 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
Tmin = 0.664, Tmax = 0.922	k = −7→7
5555 measured reflections	l = −18→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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0491P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max = 0.001
3633 reflections	Δρmax = 0.41 e Å−3
307 parameters	Δρmin = −0.25 e Å−3
1 restraint	Absolute structure: Flack (1983), with 1529 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.023 (17)

	x	y	z	Uiso*/Ueq
Cu1	0.85224 (4)	0.14981 (9)	0.75536 (3)	0.04385 (16)
N1	0.6939 (3)	0.2834 (6)	0.7406 (2)	0.0385 (8)
N2	1.0094 (3)	−0.0200 (6)	0.7612 (2)	0.0472 (9)
N3	0.9778 (3)	0.3251 (6)	0.6648 (2)	0.0455 (9)
O1	0.7806 (3)	−0.0536 (5)	0.6722 (2)	0.0536 (8)
O2	0.6057 (4)	−0.1294 (5)	0.5986 (2)	0.0629 (10)
O3	0.5115 (3)	0.4941 (6)	0.6180 (2)	0.0682 (10)
H3	0.5463	0.6051	0.6103	0.102*
O4	0.8869 (3)	0.2791 (5)	0.86299 (18)	0.0534 (8)
C1	0.6697 (4)	−0.0168 (7)	0.6467 (3)	0.0455 (11)
C2	0.6124 (3)	0.1876 (7)	0.6743 (2)	0.0394 (11)
H2	0.5311	0.1589	0.6983	0.047*
C3	0.5927 (5)	0.3310 (8)	0.5981 (3)	0.0497 (12)
H3A	0.6723	0.3871	0.5820	0.060*
H3B	0.5578	0.2532	0.5505	0.060*
C4	0.6521 (4)	0.4288 (7)	0.7864 (3)	0.0406 (10)
H4	0.5715	0.4751	0.7738	0.049*
C5	0.7188 (4)	0.5272 (7)	0.8559 (3)	0.0412 (10)
C6	0.8261 (4)	0.4355 (8)	0.8927 (3)	0.0463 (11)
C7	0.8738 (4)	0.5219 (9)	0.9718 (3)	0.0568 (13)
H7	0.9410	0.4577	0.9997	0.068*
C8	0.8240 (4)	0.6931 (9)	1.0064 (3)	0.0602 (15)
H8	0.8578	0.7431	1.0574	0.072*
C9	0.7211 (4)	0.7988 (8)	0.9669 (3)	0.0524 (12)
C10	0.6680 (4)	0.7142 (6)	0.8910 (3)	0.0434 (12)
C11	0.5671 (4)	0.8226 (8)	0.8529 (3)	0.0534 (12)
H11	0.5300	0.7711	0.8032	0.064*
C12	0.5216 (5)	1.0034 (8)	0.8871 (3)	0.0596 (13)
H12	0.4540	1.0702	0.8607	0.071*
C13	0.5764 (5)	1.0859 (8)	0.9608 (3)	0.0642 (15)
H13	0.5467	1.2085	0.9833	0.077*
C14	0.6735 (5)	0.9856 (9)	0.9992 (3)	0.0636 (14)
H14	0.7099	1.0412	1.0484	0.076*
C15	1.0230 (5)	−0.1874 (8)	0.8073 (3)	0.0621 (14)
H15	0.9624	−0.2191	0.8460	0.075*
C16	1.1243 (5)	−0.3193 (11)	0.8008 (4)	0.0776 (17)
H16	1.1298	−0.4381	0.8339	0.093*
C17	1.2155 (5)	−0.2738 (9)	0.7458 (4)	0.0780 (18)
H17	1.2840	−0.3608	0.7415	0.094*
C18	1.2056 (4)	−0.0959 (8)	0.6958 (3)	0.0564 (13)
C19	1.0996 (4)	0.0292 (8)	0.7055 (3)	0.0481 (11)
C20	1.0833 (4)	0.2127 (7)	0.6554 (3)	0.0429 (12)
C21	1.1751 (4)	0.2679 (9)	0.5972 (3)	0.0548 (12)
C22	1.1553 (5)	0.4525 (10)	0.5521 (3)	0.0694 (16)
H22	1.2140	0.4970	0.5141	0.083*
C23	1.0512 (5)	0.5663 (8)	0.5637 (3)	0.0671 (15)
H23	1.0383	0.6891	0.5340	0.080*
C24	0.9638 (4)	0.4976 (8)	0.6204 (3)	0.0552 (12)
H24	0.8924	0.5764	0.6274	0.066*
C25	1.2954 (4)	−0.0334 (11)	0.6350 (4)	0.0730 (17)
H25	1.3658	−0.1147	0.6282	0.088*
C26	1.2811 (4)	0.1357 (14)	0.5886 (3)	0.0708 (15)
H26	1.3409	0.1694	0.5496	0.085*

	U11	U22	U33	U12	U13	U23
Cu1	0.0443 (3)	0.0443 (3)	0.0434 (3)	0.0024 (3)	0.00652 (18)	−0.0022 (3)
N1	0.0436 (18)	0.036 (2)	0.0364 (18)	−0.0015 (16)	0.0031 (15)	−0.0063 (16)
N2	0.050 (2)	0.046 (2)	0.046 (2)	−0.0002 (18)	−0.0006 (17)	0.0024 (19)
N3	0.052 (2)	0.042 (2)	0.043 (2)	−0.0019 (19)	0.0020 (16)	0.0027 (18)
O1	0.0538 (19)	0.048 (2)	0.059 (2)	0.0080 (16)	0.0002 (16)	−0.0130 (17)
O2	0.075 (2)	0.048 (2)	0.066 (2)	−0.002 (2)	−0.0035 (19)	−0.0200 (19)
O3	0.068 (2)	0.047 (2)	0.089 (3)	0.0030 (19)	−0.0033 (19)	0.002 (2)
O4	0.0529 (17)	0.063 (2)	0.0442 (17)	0.0077 (17)	−0.0007 (14)	−0.0051 (16)
C1	0.054 (3)	0.040 (3)	0.043 (2)	−0.006 (2)	0.008 (2)	−0.006 (2)
C2	0.0393 (19)	0.040 (3)	0.039 (2)	−0.005 (2)	0.0038 (16)	−0.011 (2)
C3	0.058 (3)	0.046 (3)	0.045 (3)	−0.006 (3)	0.000 (2)	0.002 (2)
C4	0.039 (2)	0.041 (3)	0.042 (2)	−0.002 (2)	0.0012 (18)	−0.002 (2)
C5	0.046 (2)	0.042 (3)	0.036 (2)	−0.006 (2)	0.0052 (19)	−0.004 (2)
C6	0.047 (2)	0.053 (3)	0.039 (2)	−0.007 (2)	0.0077 (19)	−0.004 (2)
C7	0.051 (3)	0.072 (4)	0.047 (3)	−0.001 (3)	−0.003 (2)	−0.006 (3)
C8	0.066 (3)	0.069 (5)	0.045 (2)	−0.011 (3)	−0.002 (2)	−0.022 (3)
C9	0.057 (3)	0.050 (3)	0.051 (3)	−0.010 (2)	0.012 (2)	−0.014 (2)
C10	0.054 (2)	0.042 (3)	0.036 (2)	−0.007 (2)	0.0115 (19)	−0.0030 (18)
C11	0.064 (3)	0.052 (3)	0.045 (3)	−0.004 (3)	0.011 (2)	−0.003 (2)
C12	0.073 (3)	0.048 (3)	0.058 (3)	0.004 (3)	0.018 (3)	−0.003 (3)
C13	0.085 (4)	0.047 (4)	0.061 (3)	−0.002 (3)	0.024 (3)	−0.013 (2)
C14	0.075 (3)	0.058 (4)	0.058 (3)	−0.013 (3)	0.010 (3)	−0.024 (3)
C15	0.072 (3)	0.054 (3)	0.060 (3)	−0.003 (3)	−0.012 (3)	0.011 (3)
C16	0.087 (3)	0.054 (4)	0.090 (4)	0.010 (4)	−0.035 (3)	0.014 (4)
C17	0.057 (3)	0.068 (4)	0.106 (5)	0.015 (3)	−0.031 (3)	−0.014 (3)
C18	0.041 (3)	0.055 (3)	0.071 (3)	0.006 (2)	−0.012 (2)	−0.017 (3)
C19	0.039 (2)	0.052 (3)	0.053 (3)	−0.001 (2)	−0.005 (2)	−0.014 (2)
C20	0.037 (2)	0.049 (3)	0.043 (2)	−0.0048 (19)	0.0044 (18)	−0.006 (2)
C21	0.048 (3)	0.065 (3)	0.052 (3)	−0.014 (3)	0.008 (2)	−0.010 (3)
C22	0.076 (4)	0.080 (4)	0.053 (3)	−0.033 (3)	0.008 (3)	0.000 (3)
C23	0.087 (4)	0.057 (4)	0.057 (3)	−0.019 (3)	−0.008 (3)	0.013 (2)
C24	0.060 (3)	0.047 (3)	0.058 (3)	−0.004 (2)	−0.010 (2)	0.004 (2)
C25	0.041 (3)	0.082 (5)	0.097 (5)	0.003 (3)	0.009 (3)	−0.035 (4)
C26	0.049 (3)	0.092 (4)	0.072 (3)	−0.013 (4)	0.018 (2)	−0.027 (5)

Cu1—N1	1.914 (3)	C9—C14	1.415 (7)
Cu1—N2	2.012 (4)	C9—C10	1.419 (6)
Cu1—N3	2.297 (4)	C10—C11	1.407 (6)
Cu1—O1	1.994 (3)	C11—C12	1.385 (7)
Cu1—O4	1.920 (3)	C11—H11	0.9300
N1—C4	1.278 (5)	C12—C13	1.393 (7)
N1—C2	1.477 (5)	C12—H12	0.9300
N2—C15	1.310 (6)	C13—C14	1.353 (7)
N2—C19	1.367 (6)	C13—H13	0.9300
N3—C24	1.324 (6)	C14—H14	0.9300
N3—C20	1.358 (5)	C15—C16	1.388 (7)
O1—C1	1.267 (5)	C15—H15	0.9300
O2—C1	1.242 (5)	C16—C17	1.363 (8)
O3—C3	1.411 (6)	C16—H16	0.9300
O3—H3	0.8200	C17—C18	1.398 (8)
O4—C6	1.300 (5)	C17—H17	0.9300
C1—C2	1.527 (6)	C18—C19	1.408 (6)
C2—C3	1.528 (6)	C18—C25	1.441 (8)
C2—H2	0.9800	C19—C20	1.434 (6)
C3—H3A	0.9700	C20—C21	1.415 (6)
C3—H3B	0.9700	C21—C22	1.403 (8)
C4—C5	1.438 (6)	C21—C26	1.433 (8)
C4—H4	0.9300	C22—C23	1.356 (8)
C5—C6	1.404 (6)	C22—H22	0.9300
C5—C10	1.445 (6)	C23—C24	1.391 (7)
C6—C7	1.447 (6)	C23—H23	0.9300
C7—C8	1.353 (7)	C24—H24	0.9300
C7—H7	0.9300	C25—C26	1.323 (9)
C8—C9	1.424 (7)	C25—H25	0.9300
C8—H8	0.9300	C26—H26	0.9300
N1—Cu1—O4	93.23 (13)	C14—C9—C8	122.4 (5)
N1—Cu1—O1	84.06 (14)	C10—C9—C8	117.9 (4)
O4—Cu1—O1	158.33 (14)	C11—C10—C9	116.8 (4)
N1—Cu1—N2	172.54 (16)	C11—C10—C5	123.2 (4)
O4—Cu1—N2	93.43 (14)	C9—C10—C5	120.0 (4)
O1—Cu1—N2	88.51 (14)	C12—C11—C10	122.0 (4)
N1—Cu1—N3	103.78 (14)	C12—C11—H11	119.0
O4—Cu1—N3	103.66 (14)	C10—C11—H11	119.0
O1—Cu1—N3	97.86 (13)	C11—C12—C13	120.3 (5)
N2—Cu1—N3	77.87 (14)	C11—C12—H12	119.8
C4—N1—C2	120.0 (3)	C13—C12—H12	119.8
C4—N1—Cu1	126.2 (3)	C14—C13—C12	119.2 (5)
C2—N1—Cu1	113.5 (3)	C14—C13—H13	120.4
C15—N2—C19	118.8 (4)	C12—C13—H13	120.4
C15—N2—Cu1	123.7 (3)	C13—C14—C9	122.0 (5)
C19—N2—Cu1	117.0 (3)	C13—C14—H14	119.0
C24—N3—C20	118.2 (4)	C9—C14—H14	119.0
C24—N3—Cu1	133.4 (3)	N2—C15—C16	122.7 (5)
C20—N3—Cu1	108.2 (3)	N2—C15—H15	118.7
C1—O1—Cu1	115.0 (3)	C16—C15—H15	118.7
C3—O3—H3	109.5	C17—C16—C15	119.7 (6)
C6—O4—Cu1	125.0 (3)	C17—C16—H16	120.2
O2—C1—O1	125.3 (4)	C15—C16—H16	120.2
O2—C1—C2	117.5 (4)	C16—C17—C18	119.7 (5)
O1—C1—C2	117.1 (4)	C16—C17—H17	120.2
N1—C2—C1	109.3 (3)	C18—C17—H17	120.2
N1—C2—C3	111.4 (4)	C17—C18—C19	117.3 (5)
C1—C2—C3	110.3 (3)	C17—C18—C25	124.6 (5)
N1—C2—H2	108.6	C19—C18—C25	118.1 (5)
C1—C2—H2	108.6	N2—C19—C18	121.8 (5)
C3—C2—H2	108.6	N2—C19—C20	118.2 (4)
O3—C3—C2	110.4 (4)	C18—C19—C20	120.0 (4)
O3—C3—H3A	109.6	N3—C20—C21	122.5 (4)
C2—C3—H3A	109.6	N3—C20—C19	118.0 (4)
O3—C3—H3B	109.6	C21—C20—C19	119.5 (4)
C2—C3—H3B	109.6	C22—C21—C20	116.6 (5)
H3A—C3—H3B	108.1	C22—C21—C26	124.5 (5)
N1—C4—C5	125.7 (4)	C20—C21—C26	118.9 (5)
N1—C4—H4	117.2	C23—C22—C21	120.3 (5)
C5—C4—H4	117.2	C23—C22—H22	119.8
C6—C5—C4	120.6 (4)	C21—C22—H22	119.8
C6—C5—C10	120.6 (4)	C22—C23—C24	119.3 (5)
C4—C5—C10	118.6 (4)	C22—C23—H23	120.3
O4—C6—C5	126.5 (4)	C24—C23—H23	120.3
O4—C6—C7	116.4 (4)	N3—C24—C23	122.9 (5)
C5—C6—C7	117.1 (4)	N3—C24—H24	118.5
C8—C7—C6	122.1 (5)	C23—C24—H24	118.5
C8—C7—H7	118.9	C26—C25—C18	122.3 (5)
C6—C7—H7	118.9	C26—C25—H25	118.9
C7—C8—C9	121.8 (4)	C18—C25—H25	118.9
C7—C8—H8	119.1	C25—C26—C21	121.2 (5)
C9—C8—H8	119.1	C25—C26—H26	119.4
C14—C9—C10	119.6 (5)	C21—C26—H26	119.4
O4—Cu1—N1—C4	9.5 (4)	C7—C8—C9—C10	2.6 (7)
O1—Cu1—N1—C4	168.0 (4)	C14—C9—C10—C11	−1.2 (6)
N3—Cu1—N1—C4	−95.4 (4)	C8—C9—C10—C11	−179.5 (4)
O4—Cu1—N1—C2	−164.0 (3)	C14—C9—C10—C5	177.9 (4)
O1—Cu1—N1—C2	−5.6 (3)	C8—C9—C10—C5	−0.4 (6)
N3—Cu1—N1—C2	91.1 (3)	C6—C5—C10—C11	174.5 (4)
O4—Cu1—N2—C15	77.5 (4)	C4—C5—C10—C11	−10.0 (6)
O1—Cu1—N2—C15	−80.9 (4)	C6—C5—C10—C9	−4.5 (6)
N3—Cu1—N2—C15	−179.3 (4)	C4—C5—C10—C9	170.9 (4)
O4—Cu1—N2—C19	−111.2 (3)	C9—C10—C11—C12	0.2 (6)
O1—Cu1—N2—C19	90.4 (3)	C5—C10—C11—C12	−178.9 (4)
N3—Cu1—N2—C19	−7.9 (3)	C10—C11—C12—C13	0.9 (7)
N1—Cu1—N3—C24	10.5 (4)	C11—C12—C13—C14	−1.0 (7)
O4—Cu1—N3—C24	−86.3 (4)	C12—C13—C14—C9	0.0 (7)
O1—Cu1—N3—C24	96.3 (4)	C10—C9—C14—C13	1.2 (7)
N2—Cu1—N3—C24	−176.9 (4)	C8—C9—C14—C13	179.4 (5)
N1—Cu1—N3—C20	−165.7 (3)	C19—N2—C15—C16	−1.2 (7)
O4—Cu1—N3—C20	97.4 (3)	Cu1—N2—C15—C16	170.0 (4)
O1—Cu1—N3—C20	−80.0 (3)	N2—C15—C16—C17	1.2 (8)
N2—Cu1—N3—C20	6.8 (3)	C15—C16—C17—C18	−0.6 (8)
N1—Cu1—O1—C1	−0.8 (3)	C16—C17—C18—C19	0.1 (8)
O4—Cu1—O1—C1	83.0 (5)	C16—C17—C18—C25	−179.4 (5)
N2—Cu1—O1—C1	178.6 (3)	C15—N2—C19—C18	0.6 (7)
N3—Cu1—O1—C1	−103.9 (3)	Cu1—N2—C19—C18	−171.2 (3)
N1—Cu1—O4—C6	−13.8 (4)	C15—N2—C19—C20	179.9 (4)
O1—Cu1—O4—C6	−95.8 (5)	Cu1—N2—C19—C20	8.1 (5)
N2—Cu1—O4—C6	169.6 (3)	C17—C18—C19—N2	0.0 (7)
N3—Cu1—O4—C6	91.3 (3)	C25—C18—C19—N2	179.4 (4)
Cu1—O1—C1—O2	−176.0 (4)	C17—C18—C19—C20	−179.3 (4)
Cu1—O1—C1—C2	6.9 (5)	C25—C18—C19—C20	0.1 (6)
C4—N1—C2—C1	−164.0 (4)	C24—N3—C20—C21	−3.1 (6)
Cu1—N1—C2—C1	10.0 (4)	Cu1—N3—C20—C21	173.8 (4)
C4—N1—C2—C3	73.8 (5)	C24—N3—C20—C19	178.2 (4)
Cu1—N1—C2—C3	−112.2 (3)	Cu1—N3—C20—C19	−4.9 (4)
O2—C1—C2—N1	171.6 (4)	N2—C19—C20—N3	−1.4 (6)
O1—C1—C2—N1	−11.1 (5)	C18—C19—C20—N3	177.9 (4)
O2—C1—C2—C3	−65.5 (5)	N2—C19—C20—C21	179.9 (4)
O1—C1—C2—C3	111.8 (4)	C18—C19—C20—C21	−0.8 (6)
N1—C2—C3—O3	−73.8 (4)	N3—C20—C21—C22	3.2 (7)
C1—C2—C3—O3	164.6 (4)	C19—C20—C21—C22	−178.1 (4)
C2—N1—C4—C5	176.3 (4)	N3—C20—C21—C26	−177.3 (4)
Cu1—N1—C4—C5	3.1 (6)	C19—C20—C21—C26	1.4 (7)
N1—C4—C5—C6	−16.1 (7)	C20—C21—C22—C23	−1.4 (8)
N1—C4—C5—C10	168.5 (4)	C26—C21—C22—C23	179.1 (5)
Cu1—O4—C6—C5	5.7 (6)	C21—C22—C23—C24	−0.4 (8)
Cu1—O4—C6—C7	−174.7 (3)	C20—N3—C24—C23	1.1 (7)
C4—C5—C6—O4	11.2 (7)	Cu1—N3—C24—C23	−174.8 (3)
C10—C5—C6—O4	−173.4 (4)	C22—C23—C24—N3	0.6 (8)
C4—C5—C6—C7	−168.4 (4)	C17—C18—C25—C26	179.3 (5)
C10—C5—C6—C7	7.0 (6)	C19—C18—C25—C26	−0.1 (8)
O4—C6—C7—C8	175.5 (4)	C18—C25—C26—C21	0.7 (9)
C5—C6—C7—C8	−4.8 (7)	C22—C21—C26—C25	178.1 (5)
C6—C7—C8—C9	0.0 (7)	C20—C21—C26—C25	−1.4 (8)
C7—C8—C9—C14	−175.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2i	0.82	1.84	2.659 (5)	172
C25—H25···O2ii	0.93	2.63	3.454 (6)	148

Table 1

Selected bond lengths (Å)

Cu1—N1	1.914 (3)
Cu1—N2	2.012 (4)
Cu1—N3	2.297 (4)
Cu1—O1	1.994 (3)
Cu1—O4	1.920 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2i	0.82	1.84	2.659 (5)	172
C25—H25⋯O2ii	0.93	2.63	3.454 (6)	148

Symmetry codes: (i) ; (ii) .