(2,2′-Bipyridyl-κ2N,N′)(chloranilato-κ2O,O′)copper(II)

Reinoso, S.; Vitoria, P.; San Felices, L.; Lezama, L.; Gutiérrez-Zorrilla, J.M.

doi:10.1107/S1600536805027649

(2,2′-Bipyridyl-κ²N,N′)(chloranilato-κ²O,O′)copper(II)

S. Reinoso, P. Vitoria, L. San Felices, L. Lezama and J. M. Gutiérrez-Zorrilla

The Cu atom in the title complex, [Cu(C₆Cl₂O₄)(C₁₀H₈N₂)], has a square-planar CuN₂O₂ environment. The structure is built of monomeric neutral, essentially planar, molecules stacked along the b axis, with the stacks held together by means of weak π–π, π

Cl, and π

Cu interactions. The molecules of neighbouring stacks are linked via C—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027649/ya6258sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027649/ya6258Isup2.hkl Contains datablock I

CCDC reference: 287766

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.004 Å
R factor = 0.035
wR factor = 0.065
Data-to-parameter ratio = 19.9

checkCIF/PLATON results

No syntax errors found



Alert level C
GOODF01_ALERT_2_C  The least squares goodness of fit parameter lies
            outside the range 0.80 <> 2.00
            Goodness of fit given =      0.740
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         47 Perc.
PLAT333_ALERT_2_C Large Average Benzene C-C Dist.  C13    -C18           1.45 Ang.
PLAT335_ALERT_2_C Large Benzene C-C Range          C13    -C18           0.20 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C17    -   C18    ...       1.56 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

To date, there is only one structurally characterized Cu^II complex in the literature with both 2,2-bipyridine (bpy) and the chloranilate dianion (chl) as ligands, namely the dimeric cation of [{Cu(C₁₀H₈N₂)(CH₃OH)}₂(chl)](PF₆)₂ (Fujii et al., 1994). The title monomeric neutral complex, (I), was obtained in an attempt to prepare a hybrid inorganic–metal-organic material based on the auto-assembly of the above-mentioned dimer and Keggin-type polyoxometallates.

The Cu atom in the title compound is coordinated by both the neutral bpy and the dianionic chl ligands in a chelating bidentate fashion, leading to a square-planar CuN₂O₂ coordination environment (Fig. 1).

The crystal structure shows infinite ladder-like columns of monomeric complexes stacked along the b axis (Fig. 2). In addition to intermolecular Cu1···O2ⁱ contacts [3.210 (2) Å], the stacks are held together by means of an alternating sequence of π(C7—N12)···π(chl)ⁱ, π(N1—C6)···Cl2ⁱ and π(chl)···Cu1ⁱⁱ interactions [symmetry codes: (i) −x, −y, −z; (ii) −x, 1 − y, −z], the centroid–centroid or centroid–atom distances being 3.416 (2), 3.558 (1) and 3.451 (1) Å, respectively. The stacks are connected to each other through an extended network of C—H···O hydrogen bonds (Table 2), involving those O atoms which are not coordinated to the Cu atom. These C—H···O interactions give rise to layers parallel to the ab plane.

Experimental top

Upon addition of a solution containing Cu(NO₃)₂·2H₂O (96 mg), 2,2'-bipyridine (62 mg) and chloranilic acid (42 mg) in methanol (40 ml) to a solution of K₄SiW₁₂O₄₀ (667 mg) in water (50 ml), a green precipitate was formed. The title compound was obtained as prismatic dark-red crystals by recrystallization of the precipitate in a 1:2 mixture of water and dimethyformamide. Elemental analysis, found: C 44.92, H 1.97, N 6.51%; calculated for C₁₆CuCl₂H₈N₂O₄: C 45.04, H 1.89, N 6.57%. Spectroscopic analysis: IR (Medium?, ν, cm⁻¹): 1643, 1533, 1368, 845, 774, 604, 565. Axial electron paramagnetic resonance signal: g_parallel = 2.205, g_{perpendicular} = 2.052.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: DIRDIF99.2 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

Figures top

	Fig. 1. A plot of (I), with 50% probability displacement ellipsoids. H atoms have been omitted for clarity.
	Fig. 2. (a) The ladder-like column, highlighting the intermolecular Cu—O, π–π, π···Cl and π···Cu interactions. (b) A projection of a layer on the ab plane, together with a detail of the C—H···O network.

(2,2'-Bipyridyl-κ²N,N')(chloranilato-κ²O,O')copper(II) top

Crystal data top

[Cu(C₆Cl₂O₄)(C₁₀H₈N₂)]	F(000) = 1704
M_r = 426.68	D_x = 1.831 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6500 reflections
a = 24.987 (3) Å	θ = 3.5–25°
b = 7.438 (1) Å	µ = 1.78 mm⁻¹
c = 17.215 (2) Å	T = 295 K
β = 104.57 (1)°	Prism, dark red
V = 3096.6 (7) Å³	0.14 × 0.11 × 0.06 mm
Z = 8

Data collection top

Oxford Diffraction Xcalibur diffractometer	4506 independent reflections
Radiation source: fine-focus sealed tube	2120 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
Detector resolution: 1024 × 1024 with blocks 2 × 2 pixels mm^-1	θ_max = 30.0°, θ_min = 3.3°
ω scans	h = −33→35
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2003)	k = −8→10
T_min = 0.802, T_max = 0.903	l = −24→23
14006 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.035	w = 1/[σ²(F_o²) + (0.0227P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.065	(Δ/σ)_max < 0.001
S = 0.74	Δρ_max = 0.57 e Å⁻³
4506 reflections	Δρ_min = −0.31 e Å⁻³
226 parameters

Crystal data top

[Cu(C₆Cl₂O₄)(C₁₀H₈N₂)]	V = 3096.6 (7) Å³
M_r = 426.68	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 24.987 (3) Å	µ = 1.78 mm⁻¹
b = 7.438 (1) Å	T = 295 K
c = 17.215 (2) Å	0.14 × 0.11 × 0.06 mm
β = 104.57 (1)°

Data collection top

Oxford Diffraction Xcalibur diffractometer	4506 independent reflections
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2003)	2120 reflections with I > 2σ(I)
T_min = 0.802, T_max = 0.903	R_int = 0.045
14006 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.065	H-atom parameters constrained
S = 0.74	Δρ_max = 0.57 e Å⁻³
4506 reflections	Δρ_min = −0.31 e Å⁻³
226 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.050506 (13)	0.21793 (4)	0.02153 (2)	0.03594 (11)
Cl2	−0.12598 (3)	0.18923 (10)	−0.18043 (4)	0.0448 (2)
Cl1	−0.06659 (3)	0.51922 (10)	0.17048 (4)	0.0479 (2)
O2	−0.01831 (6)	0.1861 (2)	−0.05719 (10)	0.0399 (5)
O4	−0.20367 (7)	0.3575 (3)	−0.09432 (12)	0.0504 (6)
O1	0.00710 (7)	0.3375 (2)	0.08286 (10)	0.0402 (5)
O3	−0.17809 (7)	0.4977 (3)	0.05564 (12)	0.0516 (6)
N12	0.09663 (8)	0.1055 (3)	−0.04055 (12)	0.0294 (5)
C14	−0.04423 (10)	0.3515 (3)	0.04461 (15)	0.0297 (6)
N1	0.12136 (8)	0.2463 (3)	0.10076 (12)	0.0299 (5)
C11	0.07935 (10)	0.0408 (3)	−0.11404 (16)	0.0345 (7)
H11	0.0418	0.0457	−0.1393	0.041*
C13	−0.08389 (10)	0.4339 (3)	0.07398 (15)	0.0295 (6)
C4	0.22449 (11)	0.2563 (4)	0.20481 (18)	0.0486 (8)
H4	0.2593	0.257	0.2406	0.058*
C5	0.21735 (11)	0.1806 (4)	0.13017 (17)	0.0411 (8)
H5	0.2474	0.133	0.1145	0.049*
C9	0.17024 (12)	−0.0388 (4)	−0.11707 (18)	0.0460 (8)
H9	0.1951	−0.0871	−0.1435	0.055*
C2	0.12891 (11)	0.3214 (3)	0.17286 (16)	0.0364 (7)
H2	0.0985	0.3692	0.1876	0.044*
C6	0.16529 (10)	0.1756 (3)	0.07862 (16)	0.0309 (6)
C7	0.15100 (10)	0.0987 (3)	−0.00320 (16)	0.0292 (6)
C17	−0.15539 (10)	0.3535 (3)	−0.05616 (16)	0.0318 (7)
C18	−0.14057 (11)	0.4355 (3)	0.03006 (17)	0.0337 (7)
C10	0.11473 (12)	−0.0332 (4)	−0.15452 (18)	0.0416 (7)
H10	0.1015	−0.0787	−0.2061	0.05*
C16	−0.11130 (10)	0.2769 (3)	−0.08430 (15)	0.0302 (6)
C8	0.18877 (11)	0.0272 (4)	−0.04072 (17)	0.0390 (7)
H8	0.2262	0.0238	−0.0147	0.047*
C3	0.17999 (12)	0.3311 (4)	0.22641 (17)	0.0430 (8)
H3	0.1843	0.3869	0.276	0.052*
C15	−0.05865 (10)	0.2665 (3)	−0.03730 (15)	0.0296 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.02128 (16)	0.0516 (2)	0.03440 (19)	0.01046 (17)	0.00610 (14)	−0.00087 (19)
Cl2	0.0357 (4)	0.0540 (5)	0.0399 (4)	0.0033 (3)	0.0008 (3)	−0.0046 (4)
Cl1	0.0517 (5)	0.0584 (5)	0.0374 (4)	0.0070 (4)	0.0183 (4)	−0.0028 (4)
O2	0.0229 (10)	0.0592 (13)	0.0368 (11)	0.0125 (9)	0.0061 (8)	−0.0099 (10)
O4	0.0215 (10)	0.0682 (15)	0.0592 (14)	0.0086 (10)	0.0058 (10)	0.0048 (11)
O1	0.0203 (10)	0.0626 (14)	0.0356 (11)	0.0096 (9)	0.0030 (8)	−0.0060 (10)
O3	0.0313 (11)	0.0638 (14)	0.0655 (14)	0.0152 (10)	0.0230 (10)	−0.0007 (12)
N12	0.0231 (12)	0.0357 (13)	0.0303 (13)	0.0058 (10)	0.0084 (10)	0.0050 (11)
C14	0.0255 (14)	0.0323 (16)	0.0325 (16)	0.0050 (12)	0.0095 (12)	0.0080 (13)
N1	0.0241 (11)	0.0380 (15)	0.0282 (12)	0.0055 (10)	0.0077 (9)	0.0032 (11)
C11	0.0264 (15)	0.0382 (18)	0.0389 (17)	0.0063 (13)	0.0080 (13)	0.0047 (15)
C13	0.0294 (15)	0.0337 (16)	0.0284 (15)	0.0052 (12)	0.0129 (12)	0.0028 (13)
C4	0.0275 (15)	0.063 (2)	0.0475 (19)	−0.0043 (15)	−0.0051 (14)	0.0070 (18)
C5	0.0222 (15)	0.052 (2)	0.0482 (19)	0.0055 (13)	0.0073 (14)	0.0095 (16)
C9	0.0410 (19)	0.052 (2)	0.053 (2)	0.0091 (15)	0.0264 (16)	−0.0021 (17)
C2	0.0346 (16)	0.0415 (19)	0.0356 (17)	0.0043 (13)	0.0137 (14)	0.0061 (14)
C6	0.0229 (14)	0.0348 (17)	0.0352 (16)	0.0045 (12)	0.0078 (12)	0.0097 (13)
C7	0.0243 (14)	0.0279 (15)	0.0372 (17)	0.0058 (11)	0.0112 (13)	0.0078 (13)
C17	0.0217 (14)	0.0324 (16)	0.0419 (18)	0.0035 (12)	0.0091 (13)	0.0114 (14)
C18	0.0271 (15)	0.0308 (17)	0.0465 (18)	0.0069 (12)	0.0154 (14)	0.0128 (14)
C10	0.0434 (19)	0.0447 (19)	0.0399 (17)	0.0024 (15)	0.0165 (15)	−0.0027 (15)
C16	0.0253 (14)	0.0306 (16)	0.0334 (15)	0.0035 (12)	0.0050 (12)	0.0022 (14)
C8	0.0246 (15)	0.0438 (19)	0.051 (2)	0.0079 (13)	0.0134 (14)	0.0044 (16)
C3	0.0416 (18)	0.052 (2)	0.0314 (16)	−0.0069 (15)	0.0022 (15)	0.0048 (15)
C15	0.0223 (14)	0.0329 (16)	0.0351 (16)	0.0047 (12)	0.0098 (12)	0.0042 (14)

Geometric parameters (Å, º) top

Cu1—O1	1.9128 (17)	C4—C5	1.373 (4)
Cu1—O2	1.9176 (17)	C4—C3	1.376 (4)
Cu1—N1	1.956 (2)	C4—H4	0.93
Cu1—N12	1.947 (2)	C5—C6	1.378 (3)
Cl2—C16	1.730 (3)	C5—H5	0.93
Cl1—C13	1.728 (3)	C9—C8	1.370 (4)
O2—C15	1.290 (3)	C9—C10	1.375 (3)
O4—C17	1.220 (3)	C9—H9	0.93
O1—C14	1.290 (3)	C2—C3	1.376 (3)
O3—C18	1.223 (3)	C2—H2	0.93
N12—C11	1.320 (3)	C6—C7	1.478 (3)
N12—C7	1.350 (3)	C7—C8	1.378 (3)
C14—C13	1.366 (3)	C17—C16	1.429 (3)
C14—C15	1.504 (3)	C17—C18	1.561 (4)
N1—C2	1.331 (3)	C10—H10	0.93
N1—C6	1.355 (3)	C16—C15	1.362 (3)
C11—C10	1.371 (3)	C8—H8	0.93
C11—H11	0.93	C3—H3	0.93
C13—C18	1.428 (3)

O1—Cu1—O2	85.14 (7)	C10—C9—H9	120.1
O1—Cu1—N12	177.54 (8)	N1—C2—C3	122.5 (2)
O2—Cu1—N12	96.23 (8)	N1—C2—H2	118.8
O1—Cu1—N1	96.00 (8)	C3—C2—H2	118.8
O2—Cu1—N1	178.79 (8)	N1—C6—C5	120.5 (2)
N12—Cu1—N1	82.65 (9)	N1—C6—C7	113.5 (2)
C15—O2—Cu1	112.13 (15)	C5—C6—C7	125.9 (2)
C14—O1—Cu1	112.63 (15)	N12—C7—C8	121.1 (2)
C11—N12—C7	119.4 (2)	N12—C7—C6	114.4 (2)
C11—N12—Cu1	125.90 (17)	C8—C7—C6	124.5 (2)
C7—N12—Cu1	114.74 (17)	O4—C17—C16	124.7 (3)
O1—C14—C13	124.6 (2)	O4—C17—C18	117.9 (2)
O1—C14—C15	114.7 (2)	C16—C17—C18	117.4 (2)
C13—C14—C15	120.7 (2)	O3—C18—C13	124.1 (3)
C2—N1—C6	119.4 (2)	O3—C18—C17	118.1 (2)
C2—N1—Cu1	125.93 (17)	C13—C18—C17	117.8 (2)
C6—N1—Cu1	114.66 (17)	C11—C10—C9	118.5 (3)
N12—C11—C10	122.4 (3)	C11—C10—H10	120.8
N12—C11—H11	118.8	C9—C10—H10	120.8
C10—C11—H11	118.8	C15—C16—C17	122.2 (2)
C14—C13—C18	121.5 (2)	C15—C16—Cl2	119.18 (19)
C14—C13—Cl1	119.4 (2)	C17—C16—Cl2	118.59 (19)
C18—C13—Cl1	118.73 (19)	C9—C8—C7	118.8 (3)
C5—C4—C3	119.7 (3)	C9—C8—H8	120.6
C5—C4—H4	120.2	C7—C8—H8	120.6
C3—C4—H4	120.2	C2—C3—C4	118.3 (3)
C4—C5—C6	119.5 (3)	C2—C3—H3	120.8
C4—C5—H5	120.2	C4—C3—H3	120.8
C6—C5—H5	120.2	O2—C15—C16	124.8 (2)
C8—C9—C10	119.8 (3)	O2—C15—C14	115.1 (2)
C8—C9—H9	120.1	C16—C15—C14	120.1 (2)

O1—Cu1—O2—C15	4.97 (17)	N1—C6—C7—N12	−2.5 (3)
N12—Cu1—O2—C15	−172.98 (17)	C5—C6—C7—N12	178.0 (2)
O2—Cu1—O1—C14	−3.75 (17)	N1—C6—C7—C8	176.7 (2)
N1—Cu1—O1—C14	176.66 (17)	C5—C6—C7—C8	−2.8 (4)
O2—Cu1—N12—C11	2.1 (2)	C14—C13—C18—O3	175.4 (3)
N1—Cu1—N12—C11	−178.4 (2)	Cl1—C13—C18—O3	1.8 (4)
O2—Cu1—N12—C7	−179.08 (17)	C14—C13—C18—C17	−4.9 (4)
N1—Cu1—N12—C7	0.47 (17)	Cl1—C13—C18—C17	−178.53 (18)
Cu1—O1—C14—C13	−178.7 (2)	O4—C17—C18—O3	0.9 (4)
Cu1—O1—C14—C15	2.0 (3)	C16—C17—C18—O3	−178.3 (2)
O1—Cu1—N1—C2	2.5 (2)	O4—C17—C18—C13	−178.8 (2)
N12—Cu1—N1—C2	−179.6 (2)	C16—C17—C18—C13	2.0 (3)
O1—Cu1—N1—C6	−179.83 (17)	N12—C11—C10—C9	−0.5 (4)
N12—Cu1—N1—C6	−1.90 (17)	C8—C9—C10—C11	0.7 (4)
C7—N12—C11—C10	−0.2 (4)	O4—C17—C16—C15	−176.0 (2)
Cu1—N12—C11—C10	178.6 (2)	C18—C17—C16—C15	3.1 (4)
O1—C14—C13—C18	−176.4 (2)	O4—C17—C16—Cl2	2.3 (4)
C15—C14—C13—C18	2.9 (4)	C18—C17—C16—Cl2	−178.59 (17)
O1—C14—C13—Cl1	−2.8 (4)	C10—C9—C8—C7	−0.3 (4)
C15—C14—C13—Cl1	176.45 (18)	N12—C7—C8—C9	−0.4 (4)
C3—C4—C5—C6	−2.0 (4)	C6—C7—C8—C9	−179.5 (3)
C6—N1—C2—C3	0.2 (4)	N1—C2—C3—C4	−1.5 (4)
Cu1—N1—C2—C3	177.82 (19)	C5—C4—C3—C2	2.4 (4)
C2—N1—C6—C5	0.2 (4)	Cu1—O2—C15—C16	175.3 (2)
Cu1—N1—C6—C5	−177.64 (19)	Cu1—O2—C15—C14	−5.1 (3)
C2—N1—C6—C7	−179.3 (2)	C17—C16—C15—O2	174.1 (2)
Cu1—N1—C6—C7	2.8 (3)	Cl2—C16—C15—O2	−4.1 (4)
C4—C5—C6—N1	0.7 (4)	C17—C16—C15—C14	−5.4 (4)
C4—C5—C6—C7	−179.9 (3)	Cl2—C16—C15—C14	176.36 (18)
C11—N12—C7—C8	0.7 (4)	O1—C14—C15—O2	2.2 (3)
Cu1—N12—C7—C8	−178.3 (2)	C13—C14—C15—O2	−177.2 (2)
C11—N12—C7—C6	179.8 (2)	O1—C14—C15—C16	−178.2 (2)
Cu1—N12—C7—C6	0.9 (3)	C13—C14—C15—C16	2.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3ⁱ	0.93	2.54	3.465 (3)	173
C8—H8···O3ⁱ	0.93	2.40	3.330 (3)	177
C9—H9···O4ⁱ	0.93	2.49	3.171 (4)	130

Symmetry code: (i) x+1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	[Cu(C₆Cl₂O₄)(C₁₀H₈N₂)]
M_r	426.68
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	295
a, b, c (Å)	24.987 (3), 7.438 (1), 17.215 (2)
β (°)	104.57 (1)
V (Å³)	3096.6 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.78
Crystal size (mm)	0.14 × 0.11 × 0.06

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer
Absorption correction	Analytical (CrysAlis RED; Oxford Diffraction, 2003)
T_min, T_max	0.802, 0.903
No. of measured, independent and observed [I > 2σ(I)] reflections	14006, 4506, 2120
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.065, 0.74
No. of reflections	4506
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.31

Computer programs: CrysAlis CCD (Oxford Diffraction, 2003), CrysAlis RED (Oxford Diffraction, 2003), CrysAlis RED, DIRDIF99.2 (Beurskens et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX publication routines (Farrugia, 1999).

Selected geometric parameters (Å, º) top

Cu1—O1	1.9128 (17)	Cu1—N1	1.956 (2)
Cu1—O2	1.9176 (17)	Cu1—N12	1.947 (2)

O1—Cu1—O2	85.14 (7)	O1—Cu1—N1	96.00 (8)
O1—Cu1—N12	177.54 (8)	O2—Cu1—N1	178.79 (8)
O2—Cu1—N12	96.23 (8)	N12—Cu1—N1	82.65 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3ⁱ	0.93	2.54	3.465 (3)	173
C8—H8···O3ⁱ	0.93	2.40	3.330 (3)	177
C9—H9···O4ⁱ	0.93	2.49	3.171 (4)	130

Symmetry code: (i) x+1/2, y−1/2, z.

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