(2,9-Dimethyl-1,10-phenanthroline-κN,N')(4-hydroxy-benzoato-κO,O')(nitrato-κO)copper(II).

In the title compound, [Cu(C(7)H(5)O(3))(NO(3))(C(14)H(12)N(2))], the Cu(II) ion is five-coordinated in a slightly distorted square-pyramidal geometry by one O atom of a nitrate anion, two O atoms of a 4-hydroxy-benzoate anion, and two N atoms from a bidentate 2,9-dimethyl-1,10-phenanthroline (dmphen) ligand. In the crystal structure, inversion-related mol-ecules are linked into dimers by O-H⋯O hydrogen bonds. The packing is further stabilized by π-π inter-actions involving the benzene rings of the dmphen and hydroxy-benzoate units, with centroid-centroid distances of 3.4930 (14) or 3.5727 (14) Å.

Related literature

For related structures, see: Xuan et al. (2007 ▶); Zhao et al. (2007 ▶); Okabe et al. (2007 ▶). For general background, see: Selvakumar et al. (2006 ▶).

Experimental

Crystal data

[Cu(C7H5O3)(NO3)(C14H12N2)]

M = 470.92

Triclinic,

a = 9.594 (1) Å

b = 9.802 (1) Å

c = 12.347 (1) Å

α = 78.687 (14)°

β = 70.409 (13)°

γ = 63.740 (12)°

V = 979.4 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.16 mm−1

T = 291 (2) K

0.37 × 0.30 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.673, T max = 0.830

7393 measured reflections

3613 independent reflections

3129 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.082

S = 1.02

3613 reflections

283 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808034788/ci2692sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034788/ci2692Isup2.hkl

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

[Cu(C7H5O3)(NO3)(C14H12N2)]	Z = 2
Mr = 470.92	F(000) = 482
Triclinic, P1	Dx = 1.597 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.594 (1) Å	Cell parameters from 3492 reflections
b = 9.802 (1) Å	θ = 2.5–26.8°
c = 12.347 (1) Å	µ = 1.16 mm−1
α = 78.687 (14)°	T = 291 K
β = 70.409 (13)°	Block, green
γ = 63.740 (12)°	0.37 × 0.30 × 0.17 mm
V = 979.4 (2) Å3

Bruker SMART CCD area-detector diffractometer	3613 independent reflections
Radiation source: fine-focus sealed tube	3129 reflections with I > 2σ(I)
graphite	Rint = 0.016
φ and ω scans	θmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −11→11
Tmin = 0.673, Tmax = 0.830	k = −11→11
7393 measured reflections	l = −14→14

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0426P)2 + 0.3425P] where P = (Fo2 + 2Fc2)/3
3613 reflections	(Δ/σ)max = 0.001
283 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.28 e Å−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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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	0.56944 (3)	0.10556 (3)	0.31286 (2)	0.04415 (11)
O1	0.3621 (2)	0.0772 (2)	0.38002 (17)	0.0671 (5)
O2	0.4119 (2)	0.2318 (2)	0.44919 (15)	0.0621 (5)
O3	−0.33023 (19)	0.4060 (2)	0.72945 (16)	0.0582 (4)
H3	−0.3541	0.4863	0.7561	0.087*
O4	0.4677 (2)	0.3057 (2)	0.18943 (16)	0.0622 (5)
O5	0.4474 (2)	0.1655 (2)	0.08484 (18)	0.0701 (5)
O6	0.3103 (3)	0.4068 (3)	0.0818 (2)	0.1043 (9)
N1	0.7212 (2)	−0.0741 (2)	0.21653 (16)	0.0421 (4)
N2	0.7676 (2)	0.1464 (2)	0.28006 (16)	0.0422 (4)
N3	0.4092 (2)	0.2916 (2)	0.11642 (18)	0.0504 (5)
C1	0.5285 (3)	−0.1813 (3)	0.2297 (3)	0.0715 (8)
H1A	0.5038	−0.2040	0.3114	0.107*
H1B	0.5249	−0.2569	0.1929	0.107*
H1C	0.4503	−0.0827	0.2133	0.107*
C2	0.6932 (3)	−0.1819 (3)	0.1857 (2)	0.0510 (6)
C3	0.8195 (4)	−0.2957 (3)	0.1132 (2)	0.0641 (7)
H3A	0.7983	−0.3690	0.0920	0.077*
C4	0.9713 (3)	−0.3004 (3)	0.0738 (2)	0.0625 (7)
H4	1.0537	−0.3774	0.0270	0.075*
C5	1.0041 (3)	−0.1884 (3)	0.10370 (19)	0.0496 (6)
C6	1.1587 (3)	−0.1807 (3)	0.0638 (2)	0.0602 (7)
H6	1.2452	−0.2542	0.0160	0.072*
C7	1.1814 (3)	−0.0682 (3)	0.0943 (2)	0.0598 (7)
H7	1.2828	−0.0648	0.0666	0.072*
C8	1.0515 (3)	0.0449 (3)	0.1683 (2)	0.0498 (6)
C9	1.0668 (3)	0.1644 (4)	0.2035 (2)	0.0643 (7)
H9	1.1659	0.1724	0.1787	0.077*
C10	0.9371 (3)	0.2677 (4)	0.2736 (3)	0.0665 (7)
H10	0.9485	0.3463	0.2964	0.080*
C11	0.7859 (3)	0.2593 (3)	0.3126 (2)	0.0522 (6)
C12	0.6441 (3)	0.3759 (3)	0.3901 (3)	0.0737 (8)
H12A	0.5606	0.4308	0.3523	0.111*
H12B	0.6781	0.4456	0.4075	0.111*
H12C	0.6030	0.3258	0.4602	0.111*
C13	0.8981 (2)	0.0411 (3)	0.20915 (18)	0.0406 (5)
C14	0.8733 (3)	−0.0774 (2)	0.17599 (18)	0.0410 (5)
C15	0.3136 (3)	0.1778 (3)	0.4508 (2)	0.0473 (5)
C16	0.1466 (3)	0.2347 (3)	0.52814 (18)	0.0417 (5)
C17	0.0886 (3)	0.3593 (3)	0.59319 (19)	0.0470 (5)
H17	0.1576	0.4037	0.5909	0.056*
C18	−0.0697 (3)	0.4184 (3)	0.6611 (2)	0.0468 (5)
H18	−0.1069	0.5020	0.7041	0.056*
C19	−0.1735 (3)	0.3527 (3)	0.66513 (19)	0.0431 (5)
C20	−0.1163 (3)	0.2265 (3)	0.6021 (2)	0.0496 (6)
H20	−0.1845	0.1806	0.6060	0.060*
C21	0.0425 (3)	0.1690 (3)	0.5334 (2)	0.0481 (5)
H21	0.0798	0.0855	0.4903	0.058*

	U11	U22	U33	U12	U13	U23
Cu1	0.03013 (15)	0.04953 (18)	0.05171 (18)	−0.01577 (12)	−0.00692 (11)	−0.00997 (12)
O1	0.0446 (9)	0.0701 (12)	0.0827 (13)	−0.0273 (9)	0.0080 (9)	−0.0326 (10)
O2	0.0428 (9)	0.0921 (14)	0.0585 (10)	−0.0370 (9)	0.0016 (8)	−0.0242 (9)
O3	0.0380 (9)	0.0583 (11)	0.0737 (12)	−0.0203 (8)	−0.0022 (8)	−0.0164 (9)
O4	0.0612 (11)	0.0592 (11)	0.0719 (12)	−0.0204 (9)	−0.0303 (10)	−0.0054 (9)
O5	0.0574 (11)	0.0630 (12)	0.0845 (14)	−0.0193 (9)	−0.0084 (10)	−0.0260 (10)
O6	0.1100 (19)	0.0705 (14)	0.129 (2)	0.0055 (13)	−0.0824 (17)	−0.0155 (14)
N1	0.0362 (9)	0.0428 (10)	0.0467 (10)	−0.0140 (8)	−0.0142 (8)	−0.0023 (8)
N2	0.0334 (9)	0.0479 (10)	0.0472 (10)	−0.0164 (8)	−0.0136 (8)	−0.0037 (8)
N3	0.0319 (10)	0.0550 (13)	0.0567 (12)	−0.0123 (9)	−0.0060 (9)	−0.0118 (10)
C1	0.0650 (17)	0.0609 (17)	0.105 (2)	−0.0342 (14)	−0.0248 (16)	−0.0169 (16)
C2	0.0521 (14)	0.0424 (13)	0.0617 (15)	−0.0162 (11)	−0.0243 (12)	−0.0028 (11)
C3	0.0733 (19)	0.0473 (14)	0.0741 (18)	−0.0150 (13)	−0.0308 (15)	−0.0147 (13)
C4	0.0585 (16)	0.0519 (15)	0.0574 (16)	0.0012 (12)	−0.0186 (13)	−0.0148 (12)
C5	0.0440 (13)	0.0516 (14)	0.0397 (12)	−0.0069 (10)	−0.0137 (10)	−0.0015 (10)
C6	0.0371 (13)	0.0738 (18)	0.0433 (14)	−0.0045 (12)	−0.0047 (10)	−0.0027 (12)
C7	0.0319 (12)	0.0829 (19)	0.0499 (14)	−0.0182 (12)	−0.0061 (10)	0.0056 (13)
C8	0.0356 (12)	0.0675 (16)	0.0433 (13)	−0.0215 (11)	−0.0122 (10)	0.0063 (11)
C9	0.0444 (14)	0.091 (2)	0.0704 (18)	−0.0419 (14)	−0.0157 (13)	0.0026 (15)
C10	0.0567 (16)	0.0772 (19)	0.084 (2)	−0.0401 (15)	−0.0211 (15)	−0.0098 (16)
C11	0.0445 (13)	0.0579 (15)	0.0634 (15)	−0.0236 (11)	−0.0204 (11)	−0.0074 (12)
C12	0.0550 (16)	0.0690 (18)	0.106 (2)	−0.0223 (14)	−0.0214 (16)	−0.0340 (17)
C13	0.0326 (11)	0.0506 (13)	0.0363 (11)	−0.0159 (9)	−0.0120 (9)	0.0038 (9)
C14	0.0344 (11)	0.0448 (12)	0.0385 (11)	−0.0107 (9)	−0.0139 (9)	0.0021 (9)
C15	0.0407 (12)	0.0554 (14)	0.0438 (13)	−0.0203 (11)	−0.0092 (10)	−0.0012 (11)
C16	0.0388 (11)	0.0499 (13)	0.0374 (11)	−0.0214 (10)	−0.0092 (9)	0.0005 (10)
C17	0.0432 (12)	0.0598 (14)	0.0459 (13)	−0.0306 (11)	−0.0088 (10)	−0.0033 (11)
C18	0.0475 (13)	0.0489 (13)	0.0458 (13)	−0.0230 (11)	−0.0068 (10)	−0.0093 (10)
C19	0.0355 (11)	0.0477 (12)	0.0433 (12)	−0.0172 (10)	−0.0091 (9)	0.0003 (10)
C20	0.0418 (12)	0.0523 (14)	0.0610 (15)	−0.0259 (11)	−0.0104 (11)	−0.0073 (11)
C21	0.0455 (13)	0.0465 (13)	0.0517 (14)	−0.0198 (10)	−0.0073 (10)	−0.0105 (10)

Cu1—O1	2.004 (3)	C5—C6	1.429 (4)
Cu1—N1	2.007 (3)	C6—C7	1.356 (4)
Cu1—N2	2.008 (3)	C6—H6	0.93
Cu1—O2	2.026 (2)	C7—C8	1.425 (4)
Cu1—O4	2.292 (3)	C7—H7	0.93
Cu1—C15	2.357 (3)	C8—C13	1.402 (4)
O1—C15	1.269 (3)	C8—C9	1.406 (4)
O2—C15	1.264 (3)	C9—C10	1.352 (4)
O3—C19	1.353 (3)	C9—H9	0.93
O3—H3	0.82	C10—C11	1.402 (4)
O4—N3	1.266 (3)	C10—H10	0.93
O5—N3	1.228 (3)	C11—C12	1.501 (4)
O6—N3	1.221 (3)	C12—H12A	0.96
N1—C2	1.346 (3)	C12—H12B	0.96
N1—C14	1.363 (3)	C12—H12C	0.96
N2—C11	1.345 (3)	C13—C14	1.438 (3)
N2—C13	1.370 (3)	C15—C16	1.478 (3)
C1—C2	1.486 (4)	C16—C21	1.387 (3)
C1—H1A	0.96	C16—C17	1.390 (3)
C1—H1B	0.96	C17—C18	1.380 (3)
C1—H1C	0.96	C17—H17	0.93
C2—C3	1.408 (4)	C18—C19	1.390 (3)
C3—C4	1.354 (4)	C18—H18	0.93
C3—H3A	0.93	C19—C20	1.388 (4)
C4—C5	1.409 (4)	C20—C21	1.386 (3)
C4—H4	0.93	C20—H20	0.93
C5—C14	1.406 (3)	C21—H21	0.93
O1—Cu1—N1	105.07 (10)	C6—C7—H7	119.7
O1—Cu1—N2	167.57 (8)	C8—C7—H7	119.7
N1—Cu1—N2	84.14 (10)	C13—C8—C9	116.6 (2)
O1—Cu1—O2	64.92 (9)	C13—C8—C7	119.8 (2)
N1—Cu1—O2	161.37 (8)	C9—C8—C7	123.6 (2)
N2—Cu1—O2	103.84 (9)	C10—C9—C8	119.9 (2)
O1—Cu1—O4	94.09 (10)	C10—C9—H9	120.1
N1—Cu1—O4	106.75 (12)	C8—C9—H9	120.1
N2—Cu1—O4	91.11 (10)	C9—C10—C11	121.6 (3)
O2—Cu1—O4	90.11 (12)	C9—C10—H10	119.2
O1—Cu1—C15	32.57 (9)	C11—C10—H10	119.2
N1—Cu1—C15	136.29 (9)	N2—C11—C10	119.8 (2)
N2—Cu1—C15	136.17 (10)	N2—C11—C12	119.8 (2)
O2—Cu1—C15	32.40 (8)	C10—C11—C12	120.3 (2)
O4—Cu1—C15	91.14 (10)	C11—C12—H12A	109.5
C15—O1—Cu1	89.23 (15)	C11—C12—H12B	109.5
C15—O2—Cu1	88.38 (16)	H12A—C12—H12B	109.5
C19—O3—H3	109.5	C11—C12—H12C	109.5
N3—O4—Cu1	121.09 (17)	H12A—C12—H12C	109.5
C2—N1—C14	118.7 (2)	H12B—C12—H12C	109.5
C2—N1—Cu1	130.40 (18)	N2—C13—C8	123.0 (2)
C14—N1—Cu1	110.83 (15)	N2—C13—C14	117.3 (2)
C11—N2—C13	119.1 (2)	C8—C13—C14	119.7 (2)
C11—N2—Cu1	130.43 (16)	N1—C14—C5	123.5 (2)
C13—N2—Cu1	110.44 (16)	N1—C14—C13	117.20 (19)
O6—N3—O5	121.6 (2)	C5—C14—C13	119.3 (2)
O6—N3—O4	117.7 (2)	O2—C15—O1	117.3 (2)
O5—N3—O4	120.7 (2)	O2—C15—C16	121.2 (2)
C2—C1—H1A	109.5	O1—C15—C16	121.4 (2)
C2—C1—H1B	109.5	O2—C15—Cu1	59.23 (14)
H1A—C1—H1B	109.5	O1—C15—Cu1	58.19 (13)
C2—C1—H1C	109.5	C16—C15—Cu1	174.09 (17)
H1A—C1—H1C	109.5	C21—C16—C17	118.8 (2)
H1B—C1—H1C	109.5	C21—C16—C15	120.6 (2)
N1—C2—C3	120.2 (2)	C17—C16—C15	120.5 (2)
N1—C2—C1	119.6 (2)	C18—C17—C16	121.1 (2)
C3—C2—C1	120.1 (2)	C18—C17—H17	119.5
C4—C3—C2	121.3 (3)	C16—C17—H17	119.5
C4—C3—H3A	119.4	C17—C18—C19	119.8 (2)
C2—C3—H3A	119.4	C17—C18—H18	120.1
C3—C4—C5	119.8 (2)	C19—C18—H18	120.1
C3—C4—H4	120.1	O3—C19—C20	117.7 (2)
C5—C4—H4	120.1	O3—C19—C18	122.6 (2)
C14—C5—C4	116.5 (2)	C20—C19—C18	119.7 (2)
C14—C5—C6	119.4 (2)	C21—C20—C19	120.0 (2)
C4—C5—C6	124.1 (2)	C21—C20—H20	120.0
C7—C6—C5	121.1 (2)	C19—C20—H20	120.0
C7—C6—H6	119.4	C20—C21—C16	120.7 (2)
C5—C6—H6	119.4	C20—C21—H21	119.7
C6—C7—C8	120.6 (2)	C16—C21—H21	119.7
N1—Cu1—O1—C15	165.73 (15)	C13—N2—C11—C10	0.2 (4)
N2—Cu1—O1—C15	28.8 (4)	Cu1—N2—C11—C10	−176.80 (19)
O2—Cu1—O1—C15	2.50 (14)	C13—N2—C11—C12	179.9 (2)
O4—Cu1—O1—C15	−85.71 (18)	Cu1—N2—C11—C12	3.0 (4)
O1—Cu1—O2—C15	−2.51 (14)	C9—C10—C11—N2	−0.1 (4)
N1—Cu1—O2—C15	−63.2 (3)	C9—C10—C11—C12	−179.9 (3)
N2—Cu1—O2—C15	−176.87 (14)	C11—N2—C13—C8	0.0 (3)
O4—Cu1—O2—C15	91.96 (17)	Cu1—N2—C13—C8	177.49 (17)
O1—Cu1—O4—N3	−57.54 (18)	C11—N2—C13—C14	−179.8 (2)
N1—Cu1—O4—N3	49.54 (19)	Cu1—N2—C13—C14	−2.2 (2)
N2—Cu1—O4—N3	133.76 (17)	C9—C8—C13—N2	−0.1 (3)
O2—Cu1—O4—N3	−122.40 (18)	C7—C8—C13—N2	−179.7 (2)
C15—Cu1—O4—N3	−90.02 (19)	C9—C8—C13—C14	179.6 (2)
O1—Cu1—N1—C2	9.1 (2)	C7—C8—C13—C14	0.0 (3)
N2—Cu1—N1—C2	−179.4 (2)	C2—N1—C14—C5	−0.4 (3)
O2—Cu1—N1—C2	64.0 (3)	Cu1—N1—C14—C5	−178.41 (17)
O4—Cu1—N1—C2	−90.0 (2)	C2—N1—C14—C13	178.98 (19)
C15—Cu1—N1—C2	20.2 (3)	Cu1—N1—C14—C13	1.0 (2)
O1—Cu1—N1—C14	−173.18 (14)	C4—C5—C14—N1	−0.2 (3)
N2—Cu1—N1—C14	−1.68 (14)	C6—C5—C14—N1	178.8 (2)
O2—Cu1—N1—C14	−118.3 (2)	C4—C5—C14—C13	−179.5 (2)
O4—Cu1—N1—C14	87.72 (16)	C6—C5—C14—C13	−0.5 (3)
C15—Cu1—N1—C14	−162.11 (14)	N2—C13—C14—N1	0.9 (3)
O1—Cu1—N2—C11	−42.2 (5)	C8—C13—C14—N1	−178.84 (19)
N1—Cu1—N2—C11	179.3 (2)	N2—C13—C14—C5	−179.72 (19)
O2—Cu1—N2—C11	−17.8 (2)	C8—C13—C14—C5	0.6 (3)
O4—Cu1—N2—C11	72.6 (2)	Cu1—O2—C15—O1	4.0 (2)
C15—Cu1—N2—C11	−20.2 (3)	Cu1—O2—C15—C16	−173.1 (2)
O1—Cu1—N2—C13	140.6 (3)	Cu1—O1—C15—O2	−4.1 (2)
N1—Cu1—N2—C13	2.12 (14)	Cu1—O1—C15—C16	173.1 (2)
O2—Cu1—N2—C13	165.01 (14)	O1—Cu1—C15—O2	175.8 (2)
O4—Cu1—N2—C13	−104.60 (17)	N1—Cu1—C15—O2	155.62 (14)
C15—Cu1—N2—C13	162.59 (14)	N2—Cu1—C15—O2	4.4 (2)
Cu1—O4—N3—O6	155.5 (2)	O4—Cu1—C15—O2	−88.41 (18)
Cu1—O4—N3—O5	−22.2 (3)	N1—Cu1—C15—O1	−20.2 (2)
C14—N1—C2—C3	0.2 (3)	N2—Cu1—C15—O1	−171.39 (14)
Cu1—N1—C2—C3	177.79 (18)	O2—Cu1—C15—O1	−175.8 (2)
C14—N1—C2—C1	179.5 (2)	O4—Cu1—C15—O1	95.81 (18)
Cu1—N1—C2—C1	−3.0 (3)	O2—C15—C16—C21	−176.7 (2)
N1—C2—C3—C4	0.5 (4)	O1—C15—C16—C21	6.3 (4)
C1—C2—C3—C4	−178.7 (3)	O2—C15—C16—C17	6.2 (3)
C2—C3—C4—C5	−1.1 (4)	O1—C15—C16—C17	−170.8 (2)
C3—C4—C5—C14	0.9 (4)	C21—C16—C17—C18	−0.6 (3)
C3—C4—C5—C6	−178.0 (2)	C15—C16—C17—C18	176.6 (2)
C14—C5—C6—C7	−0.1 (4)	C16—C17—C18—C19	0.1 (4)
C4—C5—C6—C7	178.8 (2)	C17—C18—C19—O3	−179.5 (2)
C5—C6—C7—C8	0.7 (4)	C17—C18—C19—C20	1.0 (3)
C6—C7—C8—C13	−0.6 (4)	O3—C19—C20—C21	178.9 (2)
C6—C7—C8—C9	179.8 (2)	C18—C19—C20—C21	−1.6 (4)
C13—C8—C9—C10	0.1 (4)	C19—C20—C21—C16	1.1 (4)
C7—C8—C9—C10	179.7 (3)	C17—C16—C21—C20	0.0 (4)
C8—C9—C10—C11	0.0 (4)	C15—C16—C21—C20	−177.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4i	0.82	1.97	2.767 (4)	164

Table 1

Selected bond lengths (Å)

Cu1—O1	2.004 (3)
Cu1—N1	2.007 (3)
Cu1—N2	2.008 (3)
Cu1—O2	2.026 (2)
Cu1—O4	2.292 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4i	0.82	1.97	2.767 (4)	164

Symmetry code: (i) .