(Benzoato-κ2O,O′)(quinoline-2-carboxyl­ato-κ2N,O)(quinoline-2-carboxylic acid-κ2N,O)copper(II)

Martins, N.D.; Ramos Silva, M.; Silva, J.A.; Matos Beja, A.; Sobral, A.J.F.N.

doi:10.1107/S1600536808014268

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Pages m829-m830

doi:10.1107/S1600536808014268

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(Benzoato-κ²O,O′)(quinoline-2-carboxylato-κ²N,O)(quinoline-2-carboxylic acid-κ²N,O)copper(II)

Nuno D. Martins,^a Manuela Ramos Silva,^a ^* Joana A. Silva,^b Ana Matos Beja ^a and Abilio J. F.N. Sobral ^b

^aCEMDRX, Physics Department, University of Coimbra, P-3004-516 Coimbra, Portugal, and ^bChemistry Department, University of Coimbra, P-3004-516 Coimbra, Portugal
^*Correspondence e-mail: manuela@pollux.fis.uc.pt

(Received 27 April 2008; accepted 12 May 2008; online 21 May 2008)

The crystal structure of the title compound, [Cu(C₁₀H₆NO₂)(C₇H₅O₂)(C₁₀H₇NO₂)], contains copper(II) ions five-coordinated in a distorted trigonal-bipyramidal environment. The equatorial plane is occupied by three O atoms, one from the carboxylate group of the benzoate ion considered as occupying a single coordination site, the other two from two carboxylate groups of the quinaldic acid and quinaldate ligands. The axial positions are occupied by the N atoms of the quinoline ring system. The metal ion lies on a twofold axis that bisects the benzoate ion. The quinaldate and quinaldic acid ligands are equivalent by symmetry, and the carboxylate/carboxyl groups are disordered. The disordered H atom is shared between the carboxylate groups of adjacent quinaldic acid molecules. Such hydrogen bonds delineate zigzag chains that run along the c axis. The structure is very similar to that of the Mn^II analog.

Related literature

For related literature, see: Zurowska et al. (2007 ); Dobrzynska et al. (2005 ); Kumar & Gandotra (1980 ); Catterick et al. (1974 ); Martins et al. (2008 ).

Experimental

Crystal data

[Cu(C₁₀H₆NO₂)(C₇H₅O₂)(C₁₀H₇NO₂)]
M_r = 529.97
Monoclinic, C 2/c
a = 19.1140 (9) Å
b = 11.4665 (5) Å
c = 12.1885 (8) Å
β = 118.788 (1)°
V = 2341.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.98 mm⁻¹
T = 293 (2) K
0.26 × 0.22 × 0.20 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.75, T_max = 0.82
27106 measured reflections
2928 independent reflections
2536 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.104
S = 1.06
2928 reflections
178 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1⋯O4ⁱ	0.82	1.76	2.560 (3)	165
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808014268/bt2705sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808014268/bt2705Isup2.hkl

checkCIF report

Comment top

Some compounds with quinoline derivatives, transition metal ions and halide ions exhibit interesting magnetic properties related with the formation of low dimensional elements (Zurowska et al., 2007; Dobrzynska et al., 2005; Kumar & Gandotra, 1980; Catterick et al., 1974). The crystal structure of the title compound, I, Cu (C₇H₅O₂) (C₁₀H₇NO₂)(C₁₀H₆NO₂), consists of copper(II) ions five-coordinated in a distorted trigonal-bipyramidal environment (Fig. 1). The equatorial plane is occupied by three oxygen atoms with Cu—O distances of 1.970 (3) and 2.0553 (16) Å. One equatorial O atom belongs to the carboxylate group of the benzoate ion and each of the two quinoline molecules supply another O atom to the Cu coordination environment. The axial positions are occupied by the nitrogen atoms of the quinoline ring system, with distance 2.0424 (16) Å. There is a two fold axis running through the metal positions and almost longitudinally through the benzoate ion, that is thus disordered over two positions. The non-coordinating benzoate O atom is situated at a 2.678 (3)Å distance from the metal ion. With the exception of above mentioned benzoate disorder, the title compound shows a very similar arrangement to that of the Mn(II) analog (Martins et al., 2008). The complexes are joined together by hydrogen bonds between the carboxylate/carboxyl groups of adjacent quinaldate/quinaldic acid molecules, forming zigzag chains that run along the c axis (Fig. 2). The shared hydrogen atom is disordered and the quinoline molecules are statistically neutral or negatively charged.

Related literature top

For related literature, see: Zurowska et al. (2007); Dobrzynska et al. (2005); Kumar & Gandotra (1980); Catterick et al. (1974); Martins et al. (2008).

Experimental top

Approximately 0.12 mmol of 2-quinolinecarboxaldehyde (Sigma, 97%) was added to 0.12 mmol of copper chloride in an 10 ml dimethylformamide/benzoic acid solution. After a few weeks, single crystals of suitable quality were grown from the solution. The refined structure shows that the crystals incorporated a different quinoline derivative than that expected showing the material purchased from Sigma was contaminated.

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEPII (Johnson, 1976) plot of the title compound. Displacement ellipsoids are drawn at the 50% level.
	Fig. 2. A chain formed via H-bonds running along the c axis.

(Benzoato-κ²O,O')(quinoline-2-carboxylato-κ²N,O)(quinoline-2-carboxylic acid-κ²N,O)copper(II) top

Crystal data top

[Cu(C₁₀H₆NO₂)(C₇H₅O₂)(C₁₀H₇NO₂)]	F(000) = 1084
M_r = 529.97	D_x = 1.504 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4050 reflections
a = 19.1140 (9) Å	θ = 3.2–26.8°
b = 11.4665 (5) Å	µ = 0.98 mm⁻¹
c = 12.1885 (8) Å	T = 293 K
β = 118.788 (1)°	Block, green
V = 2341.2 (2) Å³	0.26 × 0.22 × 0.20 mm
Z = 4

Data collection top

Bruker APEX CCD area-detector diffractometer	2928 independent reflections
Radiation source: fine-focus sealed tube	2536 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 28.4°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −24→25
T_min = 0.75, T_max = 0.82	k = −15→15
27106 measured reflections	l = −16→16

Refinement top

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0492P)² + 2.1952P] where P = (F_o² + 2F_c²)/3
2928 reflections	(Δ/σ)_max < 0.001
178 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Cu(C₁₀H₆NO₂)(C₇H₅O₂)(C₁₀H₇NO₂)]	V = 2341.2 (2) Å³
M_r = 529.97	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 19.1140 (9) Å	µ = 0.98 mm⁻¹
b = 11.4665 (5) Å	T = 293 K
c = 12.1885 (8) Å	0.26 × 0.22 × 0.20 mm
β = 118.788 (1)°

Data collection top

Bruker APEX CCD area-detector diffractometer	2928 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	2536 reflections with I > 2σ(I)
T_min = 0.75, T_max = 0.82	R_int = 0.019
27106 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.06	Δρ_max = 0.38 e Å⁻³
2928 reflections	Δρ_min = −0.32 e Å⁻³
178 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.

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cu1	0.5000	0.31494 (3)	0.2500	0.04408 (13)
O1	0.51571 (18)	0.1520 (3)	0.3083 (3)	0.0467 (7)	0.50
O2	0.47650 (18)	0.1264 (3)	0.1065 (3)	0.0517 (7)	0.50
C1	0.4960 (2)	0.0874 (4)	0.2116 (3)	0.0406 (9)	0.50
O3	0.49011 (9)	0.42154 (18)	0.10765 (18)	0.0766 (6)
H1	0.5218	0.4412	0.0837	0.115*	0.50
O4	0.39680 (14)	0.5024 (3)	−0.0713 (3)	0.1504 (15)
N1	0.37963 (10)	0.34319 (16)	0.15664 (16)	0.0460 (4)
C2	0.5000	−0.0419 (3)	0.2500	0.0568 (8)
C3	0.50955 (16)	−0.1029 (3)	0.3531 (2)	0.0671 (7)
H3	0.5165	−0.0628	0.4239	0.080*
C4	0.50904 (19)	−0.2216 (3)	0.3528 (3)	0.0774 (8)
H4	0.5149	−0.2620	0.4228	0.093*
C5	0.5000	−0.2814 (3)	0.2500	0.0767 (11)
H5	0.5000	−0.3625	0.2500	0.092*
C6	0.41763 (13)	0.4477 (2)	0.0220 (2)	0.0563 (5)
C7	0.35528 (12)	0.40982 (19)	0.05672 (19)	0.0492 (5)
C8	0.27586 (13)	0.4476 (2)	−0.0157 (2)	0.0631 (6)
H8	0.2609	0.4935	−0.0865	0.076*
C9	0.22163 (14)	0.4154 (3)	0.0204 (3)	0.0690 (7)
H9	0.1688	0.4392	−0.0260	0.083*
C10	0.24486 (14)	0.3469 (2)	0.1267 (3)	0.0632 (6)
C11	0.19152 (17)	0.3123 (3)	0.1708 (4)	0.0827 (9)
H11	0.1385	0.3361	0.1280	0.099*
C12	0.21650 (19)	0.2459 (4)	0.2729 (4)	0.0950 (11)
H12	0.1807	0.2246	0.3007	0.114*
C13	0.2958 (2)	0.2080 (3)	0.3386 (3)	0.0862 (9)
H13	0.3122	0.1617	0.4095	0.103*
C14	0.34976 (15)	0.2385 (3)	0.2997 (2)	0.0657 (6)
H14	0.4022	0.2122	0.3431	0.079*
C15	0.32525 (13)	0.30941 (19)	0.1942 (2)	0.0522 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.03721 (19)	0.03809 (19)	0.0498 (2)	0.000	0.01525 (15)	0.000
O1	0.0443 (16)	0.0374 (16)	0.0491 (16)	−0.0029 (13)	0.0152 (13)	−0.0017 (14)
O2	0.0571 (17)	0.0465 (17)	0.0476 (16)	−0.0006 (13)	0.0221 (14)	0.0053 (13)
C1	0.0313 (17)	0.039 (2)	0.047 (2)	0.0006 (17)	0.015 (2)	−0.0005 (15)
O3	0.0441 (8)	0.0868 (13)	0.0932 (13)	0.0102 (8)	0.0286 (8)	0.0495 (11)
O4	0.0687 (14)	0.217 (4)	0.144 (2)	0.0178 (17)	0.0337 (15)	0.124 (2)
N1	0.0362 (8)	0.0478 (9)	0.0496 (9)	−0.0066 (7)	0.0172 (7)	−0.0082 (7)
C2	0.0363 (13)	0.0389 (15)	0.094 (2)	0.000	0.0301 (15)	0.000
C3	0.0658 (15)	0.0756 (17)	0.0649 (14)	−0.0121 (13)	0.0356 (12)	−0.0229 (13)
C4	0.087 (2)	0.0765 (18)	0.0623 (15)	−0.0115 (15)	0.0309 (14)	0.0163 (14)
C5	0.080 (3)	0.0383 (16)	0.092 (3)	0.000	0.026 (2)	0.000
C6	0.0461 (11)	0.0635 (14)	0.0533 (11)	−0.0014 (10)	0.0192 (9)	0.0046 (10)
C7	0.0401 (10)	0.0490 (11)	0.0510 (11)	−0.0015 (8)	0.0158 (8)	−0.0064 (9)
C8	0.0441 (11)	0.0684 (15)	0.0636 (13)	0.0069 (10)	0.0155 (10)	−0.0013 (12)
C9	0.0395 (11)	0.0742 (17)	0.0812 (17)	0.0045 (11)	0.0194 (11)	−0.0122 (14)
C10	0.0425 (11)	0.0688 (15)	0.0784 (16)	−0.0107 (10)	0.0291 (11)	−0.0234 (13)
C11	0.0506 (14)	0.101 (2)	0.105 (2)	−0.0152 (14)	0.0443 (16)	−0.0185 (19)
C12	0.0675 (18)	0.126 (3)	0.114 (3)	−0.0322 (19)	0.0611 (19)	−0.022 (2)
C13	0.0775 (19)	0.106 (3)	0.088 (2)	−0.0260 (17)	0.0494 (17)	0.0001 (17)
C14	0.0536 (13)	0.0770 (17)	0.0695 (14)	−0.0168 (12)	0.0320 (12)	−0.0058 (13)
C15	0.0416 (10)	0.0560 (13)	0.0595 (12)	−0.0126 (9)	0.0247 (9)	−0.0154 (10)

Geometric parameters (Å, º) top

Cu1—O1ⁱ	1.970 (3)	C3—C4	1.361 (4)
Cu1—O1	1.970 (3)	C3—H3	0.9300
Cu1—N1	2.0424 (16)	C4—C5	1.364 (4)
Cu1—N1ⁱ	2.0424 (16)	C4—H4	0.9300
Cu1—O3ⁱ	2.0553 (16)	C5—C4ⁱ	1.364 (4)
Cu1—O3	2.0553 (16)	C5—H5	0.9300
O1—C1ⁱ	0.777 (4)	C6—C7	1.508 (3)
O1—O2ⁱ	1.018 (4)	C7—C8	1.407 (3)
O1—O1ⁱ	1.249 (7)	C8—C9	1.358 (4)
O1—C1	1.285 (4)	C8—H8	0.9300
O2—O1ⁱ	1.018 (4)	C9—C10	1.392 (4)
O2—C1	1.233 (5)	C9—H9	0.9300
C1—O1ⁱ	0.777 (4)	C10—C15	1.416 (3)
C1—C1ⁱ	0.872 (8)	C10—C11	1.419 (4)
C1—C2	1.545 (5)	C11—C12	1.336 (5)
O3—C6	1.306 (3)	C11—H11	0.9300
O3—H1	0.8200	C12—C13	1.400 (5)
O4—C6	1.187 (3)	C12—H12	0.9300
N1—C7	1.318 (3)	C13—C14	1.371 (4)
N1—C15	1.378 (3)	C13—H13	0.9300
C2—C3ⁱ	1.372 (3)	C14—C15	1.398 (4)
C2—C3	1.372 (3)	C14—H14	0.9300
C2—C1ⁱ	1.545 (5)

O1ⁱ—Cu1—O1	36.95 (19)	C3—C2—C1ⁱ	104.3 (2)
O1ⁱ—Cu1—N1	90.82 (10)	C4—C3—C2	120.7 (2)
O1—Cu1—N1	106.65 (10)	C4—C3—H3	119.6
O1ⁱ—Cu1—N1ⁱ	106.65 (10)	C2—C3—H3	119.6
O1—Cu1—N1ⁱ	90.82 (10)	C3—C4—C5	120.2 (3)
N1—Cu1—N1ⁱ	161.74 (10)	C3—C4—H4	119.9
O1ⁱ—Cu1—O3ⁱ	143.58 (12)	C5—C4—H4	119.9
O1—Cu1—O3ⁱ	108.87 (12)	C4ⁱ—C5—C4	119.6 (4)
N1—Cu1—O3ⁱ	89.83 (7)	C4ⁱ—C5—H5	120.2
N1ⁱ—Cu1—O3ⁱ	79.30 (7)	C4—C5—H5	120.2
O1ⁱ—Cu1—O3	108.87 (12)	O4—C6—O3	128.6 (2)
O1—Cu1—O3	143.58 (12)	O4—C6—C7	118.4 (2)
N1—Cu1—O3	79.30 (7)	O3—C6—C7	112.78 (19)
N1ⁱ—Cu1—O3	89.83 (7)	N1—C7—C8	123.5 (2)
O3ⁱ—Cu1—O3	107.02 (13)	N1—C7—C6	116.81 (18)
C1ⁱ—O1—O2ⁱ	85.6 (5)	C8—C7—C6	119.6 (2)
O2ⁱ—O1—O1ⁱ	156.1 (4)	C9—C8—C7	118.3 (2)
O2ⁱ—O1—C1	127.1 (3)	C9—C8—H8	120.9
C1ⁱ—O1—Cu1	145.0 (5)	C7—C8—H8	120.9
O2ⁱ—O1—Cu1	124.3 (3)	C8—C9—C10	120.3 (2)
O1ⁱ—O1—Cu1	71.52 (10)	C8—C9—H9	119.9
C1—O1—Cu1	106.8 (3)	C10—C9—H9	119.9
O1ⁱ—C1—C1ⁱ	102.2 (5)	C9—C10—C15	118.9 (2)
O1ⁱ—C1—O2	55.5 (4)	C9—C10—C11	123.0 (3)
C1ⁱ—C1—O2	157.5 (4)	C15—C10—C11	118.1 (3)
O1ⁱ—C1—O1	69.6 (5)	C12—C11—C10	120.8 (3)
O2—C1—O1	123.6 (4)	C12—C11—H11	119.6
O1ⁱ—C1—C2	166.6 (5)	C10—C11—H11	119.6
C1ⁱ—C1—C2	73.61 (15)	C11—C12—C13	120.8 (3)
O2—C1—C2	127.5 (4)	C11—C12—H12	119.6
O1—C1—C2	109.0 (3)	C13—C12—H12	119.6
C6—O3—Cu1	116.24 (14)	C14—C13—C12	120.7 (3)
C6—O3—H1	109.5	C14—C13—H13	119.7
Cu1—O3—H1	132.9	C12—C13—H13	119.7
C7—N1—C15	118.85 (18)	C13—C14—C15	119.5 (3)
C7—N1—Cu1	114.11 (14)	C13—C14—H14	120.3
C15—N1—Cu1	126.73 (15)	C15—C14—H14	120.3
C3ⁱ—C2—C3	118.6 (3)	N1—C15—C14	119.8 (2)
C3ⁱ—C2—C1	104.3 (2)	N1—C15—C10	120.2 (2)
C3—C2—C1	137.1 (2)	C14—C15—C10	120.0 (2)
C3ⁱ—C2—C1ⁱ	137.1 (2)

O1ⁱ—Cu1—O1—C1ⁱ	−15.7 (7)	O3ⁱ—Cu1—N1—C15	−65.38 (18)
N1—Cu1—O1—C1ⁱ	52.4 (9)	O3—Cu1—N1—C15	−172.74 (19)
N1ⁱ—Cu1—O1—C1ⁱ	−132.9 (8)	O1ⁱ—C1—C2—C3ⁱ	108 (2)
O3ⁱ—Cu1—O1—C1ⁱ	148.1 (8)	C1ⁱ—C1—C2—C3ⁱ	−179.0 (5)
O3—Cu1—O1—C1ⁱ	−42.1 (9)	O2—C1—C2—C3ⁱ	9.9 (5)
O1ⁱ—Cu1—O1—O2ⁱ	−159.9 (6)	O1—C1—C2—C3ⁱ	−170.9 (3)
N1—Cu1—O1—O2ⁱ	−91.8 (4)	O1ⁱ—C1—C2—C3	−72 (2)
N1ⁱ—Cu1—O1—O2ⁱ	82.8 (4)	C1ⁱ—C1—C2—C3	1.4 (7)
O3ⁱ—Cu1—O1—O2ⁱ	3.9 (4)	O2—C1—C2—C3	−169.7 (3)
O3—Cu1—O1—O2ⁱ	173.7 (3)	O1—C1—C2—C3	9.5 (4)
N1—Cu1—O1—O1ⁱ	68.1 (3)	O1ⁱ—C1—C2—C1ⁱ	−73 (2)
N1ⁱ—Cu1—O1—O1ⁱ	−117.2 (3)	O2—C1—C2—C1ⁱ	−171.1 (9)
O3ⁱ—Cu1—O1—O1ⁱ	163.8 (3)	O1—C1—C2—C1ⁱ	8.2 (3)
O3—Cu1—O1—O1ⁱ	−26.4 (4)	C3ⁱ—C2—C3—C4	−0.4 (2)
O1ⁱ—Cu1—O1—C1	5.6 (2)	C1—C2—C3—C4	179.1 (3)
N1—Cu1—O1—C1	73.7 (3)	C1ⁱ—C2—C3—C4	179.9 (3)
N1ⁱ—Cu1—O1—C1	−111.6 (2)	C2—C3—C4—C5	0.9 (4)
O3ⁱ—Cu1—O1—C1	169.4 (2)	C3—C4—C5—C4ⁱ	−0.4 (2)
O3—Cu1—O1—C1	−20.8 (3)	Cu1—O3—C6—O4	−176.0 (3)
O1ⁱ—O2—C1—C1ⁱ	6.7 (16)	Cu1—O3—C6—C7	9.5 (3)
O1ⁱ—O2—C1—O1	−15.3 (5)	C15—N1—C7—C8	−0.9 (3)
O1ⁱ—O2—C1—C2	163.8 (7)	Cu1—N1—C7—C8	−175.00 (18)
C1ⁱ—O1—C1—O1ⁱ	152.6 (11)	C15—N1—C7—C6	177.99 (18)
O2ⁱ—O1—C1—O1ⁱ	155.8 (7)	Cu1—N1—C7—C6	3.9 (2)
Cu1—O1—C1—O1ⁱ	−9.2 (4)	O4—C6—C7—N1	175.9 (3)
O2ⁱ—O1—C1—C1ⁱ	3.3 (8)	O3—C6—C7—N1	−9.0 (3)
O1ⁱ—O1—C1—C1ⁱ	−152.6 (11)	O4—C6—C7—C8	−5.2 (4)
Cu1—O1—C1—C1ⁱ	−161.7 (7)	O3—C6—C7—C8	170.0 (2)
C1ⁱ—O1—C1—O2	166.0 (10)	N1—C7—C8—C9	1.2 (4)
O2ⁱ—O1—C1—O2	169.3 (3)	C6—C7—C8—C9	−177.7 (2)
O1ⁱ—O1—C1—O2	13.4 (4)	C7—C8—C9—C10	0.1 (4)
Cu1—O1—C1—O2	4.2 (5)	C8—C9—C10—C15	−1.5 (4)
C1ⁱ—O1—C1—C2	−13.3 (5)	C8—C9—C10—C11	178.7 (3)
O2ⁱ—O1—C1—C2	−10.0 (5)	C9—C10—C11—C12	179.6 (3)
O1ⁱ—O1—C1—C2	−165.9 (6)	C15—C10—C11—C12	−0.2 (4)
Cu1—O1—C1—C2	−175.0 (2)	C10—C11—C12—C13	−0.5 (6)
O1ⁱ—Cu1—O3—C6	81.1 (2)	C11—C12—C13—C14	0.1 (6)
O1—Cu1—O3—C6	97.5 (2)	C12—C13—C14—C15	0.9 (5)
N1—Cu1—O3—C6	−6.11 (19)	C7—N1—C15—C14	179.8 (2)
N1ⁱ—Cu1—O3—C6	−171.4 (2)	Cu1—N1—C15—C14	−6.9 (3)
O3ⁱ—Cu1—O3—C6	−92.6 (2)	C7—N1—C15—C10	−0.6 (3)
O1ⁱ—Cu1—N1—C7	−108.25 (18)	Cu1—N1—C15—C10	172.68 (16)
O1—Cu1—N1—C7	−142.16 (17)	C13—C14—C15—N1	178.1 (2)
N1ⁱ—Cu1—N1—C7	55.17 (14)	C13—C14—C15—C10	−1.5 (4)
O3ⁱ—Cu1—N1—C7	108.16 (16)	C9—C10—C15—N1	1.8 (3)
O3—Cu1—N1—C7	0.80 (15)	C11—C10—C15—N1	−178.4 (2)
O1ⁱ—Cu1—N1—C15	78.21 (19)	C9—C10—C15—C14	−178.6 (2)
O1—Cu1—N1—C15	44.3 (2)	C11—C10—C15—C14	1.2 (4)
N1ⁱ—Cu1—N1—C15	−118.37 (17)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1···O4ⁱⁱ	0.82	1.76	2.560 (3)	165

Symmetry code: (ii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₀H₆NO₂)(C₇H₅O₂)(C₁₀H₇NO₂)]
M_r	529.97
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	19.1140 (9), 11.4665 (5), 12.1885 (8)
β (°)	118.788 (1)
V (Å³)	2341.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.98
Crystal size (mm)	0.26 × 0.22 × 0.20

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.75, 0.82
No. of measured, independent and observed [I > 2σ(I)] reflections	27106, 2928, 2536
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.104, 1.06
No. of reflections	2928
No. of parameters	178
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.32

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1···O4ⁱ	0.82	1.76	2.560 (3)	165.4

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

This work was supported by Fundação para a Ciência e a Tecnologia (FCT) under project POCI/FIS/57876/2004.

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