Bis­(benzimidazole-κN3)bis(2-benzoyl­benzoato-κO)copper(II)

Yıldırım, M.H.; Heren, Z.; Paşaoğlu, H.; Hıra, D.; Büyükgüngör, O.

doi:10.1107/S1600536809017139

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Pages m638-m639

doi:10.1107/S1600536809017139

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Bis(benzimidazole-κN³)bis(2-benzoylbenzoato-κO)copper(II)

M. Hakkı Yıldırım,^a ^* Zerrin Heren,^b Hümeyra Paşaoğlu,^a Derya Hıra ^b and Orhan Büyükgüngör ^a

^aDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, Kurupelit, TR-55139, Samsun, Turkey, and ^bDepartment of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayıs University, Kurupelit, TR-55139, Samsun, Turkey
^*Correspondence e-mail: yhakki@omu.edu.tr

(Received 4 May 2009; accepted 6 May 2009; online 14 May 2009)

In the title centrosymmetric mononuclear copper(II) compound, [Cu(C₁₄H₉O₃)₂(C₇H₆N₂)₂], the central Cu^II ion is coordinated by two N atoms from two symmetry-related benzimidazole (bim) ligands and two O atoms from two symmetry-related 2-benzoylbenzoate (2-byba) ligands in a square-planar geometry. The molecules are linked into chains running along the b axis by N—H⋯O hydrogen bonds and the chains are cross-linked by C—H⋯π interactions.

Related literature

For general background to 2-benzoylbenzoate, see: Diop et al. (2006 , 2007 ); Foreman et al. (2001 ); Jones et al. (1996 ); Martin & Valente (1998 ); Prout et al. (1996 ); Song et al. (2005 ). For the crystal structure of 2-benzoylbenzoate, see: Lalancette et al. (1990 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

[Cu(C₁₄H₉O₃)₂(C₇H₆N₂)₂]
M_r = 750.24
Monoclinic, P 2₁ /c
a = 10.8692 (6) Å
b = 7.4521 (3) Å
c = 23.0874 (15) Å
β = 95.111 (5)°
V = 1862.61 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.64 mm⁻¹
T = 296 K
0.41 × 0.39 × 0.23 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.550, T_max = 0.792
10706 measured reflections
3859 independent reflections
2987 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.103
S = 1.05
3859 reflections
241 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Selected bond lengths (Å)

N1—Cu1	1.9916 (17)
O1—Cu1	1.9474 (13)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.86	1.90	2.747 (2)	169 (2)
C5—H5⋯Cg1ⁱⁱ	0.93	2.67	3.560 (2)	160 (2)
C11—H11⋯Cg2ⁱⁱⁱ	0.93	2.95	3.760 (2)	146 (2)
Symmetry codes: (i) x, y-1, z; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 and Cg2 are centroids of the C9–C14 and N1/C15/N2/C16/C21 rings, respectively.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809017139/ci2798sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809017139/ci2798Isup2.hkl

checkCIF report

Comment top

Altough the crystal structure of 2-byba was investigated in 1990 (Lalancette et al., 1990), only a limited number of articles have focused on 2-byba complexes. Consequently, this study, among with our ongoing study of characterization of mixed-ligand metal complexes, will provide a new example of copper(II) complexes with 2-byba.

In title compound, the Cu^II ion lying on a centre of symmetry, is in a square-planar coordination geometry formed by two symmetry related 2-byba and two symmetry related bim ligands. Both ligands are monodentate with the 2-byba coordinates through carboxylate O atom and bim coordinates through the aromatic N atom.

The molecular packing is mainly stabilized by strong intermolecular N—H···O hydrogen bonds (Table 2 and Fig. 2) and C—H···π interactions. Atom N2 in the molecule at (x, y, z) acts as hydrogen-bond donor, via H2, to atom O2 in the molecule at (x, y - 1, z) forming C(8) chains with R₂²(16) rings (Bernstein et al., 1995). These chains run parallel to the [010] (Fig. 2). The chains are inter-connected to each other by C5—H5···Cg1ⁱⁱⁱ and C11—H11···Cg2^iv interactions along the [001] and [101], respectively. Cg1 and Cg2 are centroids of the C9–C14 and N1/C15/N2/C16/C21 rings, respectively and symmetry codes (iii) and (iv) are as in Table 2.

Related literature top

For general background to 2-benzoylbenzoate, see: Diop et al. (2006, 2007); Foreman et al. (2001); Jones et al. (1996); Martin et al. (1998); Prout et al. (1996); Song et al. (2005). For the crystal structure of 2-benzoylbenzoate, see: Lalancette et al. (1990). For graph-set notation, see: Bernstein et al. (1995). Cg1 and Cg2 are centroids of the C9–C14 and N1/C15/N2/C16/C21 rings, respectively.

Experimental top

For the preparation of the title complex, a solution of cupric acetate (0.18 g, 1 mmol) in methanol (10 ml) was added to a solution of 2-byba (0.45 g, 2 mmol) in methanol (10 ml) and the solution was stirred for 15 min at 333 K. Solution of bim (0.23 g, 2 mmol) in methanol (10 ml) was added to the former solution. Final solution was left to evaporate slowly at room temperature. After one week, violet stick crystals of the title complex were isolated.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title complex, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 20% probability. Symmetry code: (i) 1 - x, 1 - y, 1 - z.
	Fig. 2. Part of the crystal structure of the title complex showing the chain of R₂²(16) rings along [010] generated by N—H···O hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonds have been omitted for clarity.

Bis(1H-benzimidazole-κN³)bis(2-benzoylbenzoato- κO)copper(II) top

Crystal data top

[Cu(C₁₄H₉O₃)₂(C₇H₆N₂)₂]	F(000) = 774
M_r = 750.24	D_x = 1.338 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 13271 reflections
a = 10.8692 (6) Å	θ = 1.8–27.2°
b = 7.4521 (3) Å	µ = 0.64 mm⁻¹
c = 23.0874 (15) Å	T = 296 K
β = 95.111 (5)°	Block, violet
V = 1862.61 (18) Å³	0.41 × 0.39 × 0.23 mm
Z = 2

Data collection top

Stoe IPDS II diffractometer	3859 independent reflections
Radiation source: fine-focus sealed tube	2987 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 1.8°
ω scans	h = −13→13
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −9→9
T_min = 0.550, T_max = 0.792	l = −28→28
10706 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.063P)² + 0.0342P] where P = (F_o² + 2F_c²)/3
3859 reflections	(Δ/σ)_max = 0.001
241 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

[Cu(C₁₄H₉O₃)₂(C₇H₆N₂)₂]	V = 1862.61 (18) Å³
M_r = 750.24	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.8692 (6) Å	µ = 0.64 mm⁻¹
b = 7.4521 (3) Å	T = 296 K
c = 23.0874 (15) Å	0.41 × 0.39 × 0.23 mm
β = 95.111 (5)°

Data collection top

Stoe IPDS II diffractometer	3859 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2987 reflections with I > 2σ(I)
T_min = 0.550, T_max = 0.792	R_int = 0.027
10706 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.05	Δρ_max = 0.19 e Å⁻³
3859 reflections	Δρ_min = −0.43 e Å⁻³
241 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
C1	0.67880 (16)	0.5839 (2)	0.58664 (7)	0.0451 (4)
C2	0.80566 (16)	0.5833 (3)	0.61777 (7)	0.0463 (4)
C3	0.8821 (2)	0.4359 (3)	0.61387 (10)	0.0671 (6)
H3	0.8554	0.3388	0.5907	0.080*
C4	0.9978 (2)	0.4320 (4)	0.64415 (12)	0.0822 (7)
H4	1.0478	0.3314	0.6420	0.099*
C5	1.0388 (2)	0.5765 (4)	0.67729 (11)	0.0784 (7)
H5	1.1174	0.5750	0.6969	0.094*
C6	0.96404 (18)	0.7232 (3)	0.68158 (9)	0.0631 (5)
H6	0.9920	0.8200	0.7045	0.076*
C7	0.84674 (15)	0.7290 (3)	0.65200 (7)	0.0460 (4)
C8	0.77333 (16)	0.8979 (3)	0.65665 (8)	0.0512 (4)
C9	0.71310 (18)	0.9262 (4)	0.71160 (9)	0.0619 (5)
C10	0.7100 (2)	0.7915 (4)	0.75275 (10)	0.0757 (7)
H10	0.7439	0.6797	0.7461	0.091*
C11	0.6561 (3)	0.8237 (6)	0.80394 (12)	0.1086 (12)
H11	0.6537	0.7334	0.8316	0.130*
C12	0.6068 (3)	0.9868 (8)	0.81363 (17)	0.130 (2)
H12	0.5720	1.0072	0.8484	0.156*
C13	0.6068 (3)	1.1197 (7)	0.77439 (19)	0.1323 (18)
H13	0.5708	1.2295	0.7819	0.159*
C14	0.6616 (3)	1.0930 (5)	0.72159 (12)	0.1001 (11)
H14	0.6631	1.1846	0.6943	0.120*
C15	0.53325 (19)	0.1542 (3)	0.55656 (8)	0.0569 (5)
H15	0.6179	0.1741	0.5577	0.068*
C16	0.3574 (2)	0.0187 (3)	0.56527 (9)	0.0625 (5)
C17	0.2641 (3)	−0.1000 (4)	0.57604 (11)	0.0856 (8)
H17	0.2811	−0.2148	0.5904	0.103*
C18	0.1454 (3)	−0.0395 (5)	0.56439 (13)	0.0947 (9)
H18	0.0798	−0.1150	0.5707	0.114*
C19	0.1216 (2)	0.1327 (5)	0.54336 (12)	0.0886 (8)
H19	0.0398	0.1694	0.5363	0.106*
C20	0.2139 (2)	0.2516 (4)	0.53244 (10)	0.0698 (6)
H20	0.1962	0.3665	0.5184	0.084*
C21	0.33531 (19)	0.1912 (3)	0.54354 (8)	0.0564 (5)
N1	0.44902 (15)	0.2755 (2)	0.53809 (7)	0.0534 (4)
N2	0.48416 (18)	0.0022 (2)	0.57316 (8)	0.0630 (4)
H2	0.5243	−0.0906	0.5865	0.076*
O1	0.66166 (13)	0.47949 (17)	0.54318 (7)	0.0602 (4)
O2	0.59825 (11)	0.68310 (18)	0.60404 (6)	0.0527 (3)
O3	0.77108 (16)	1.0089 (2)	0.61852 (7)	0.0722 (4)
Cu1	0.5000	0.5000	0.5000	0.04882 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0432 (9)	0.0423 (9)	0.0471 (9)	0.0009 (8)	−0.0097 (7)	0.0089 (8)
C2	0.0400 (9)	0.0524 (10)	0.0444 (9)	0.0039 (8)	−0.0074 (7)	0.0045 (8)
C3	0.0575 (12)	0.0659 (13)	0.0735 (13)	0.0167 (11)	−0.0183 (10)	−0.0108 (11)
C4	0.0587 (13)	0.0899 (17)	0.0925 (17)	0.0313 (13)	−0.0228 (12)	−0.0147 (15)
C5	0.0447 (11)	0.1023 (19)	0.0831 (16)	0.0160 (12)	−0.0230 (10)	−0.0076 (15)
C6	0.0468 (10)	0.0767 (15)	0.0623 (12)	0.0013 (10)	−0.0154 (9)	−0.0075 (10)
C7	0.0391 (8)	0.0577 (11)	0.0400 (8)	0.0008 (8)	−0.0026 (7)	0.0034 (8)
C8	0.0439 (9)	0.0549 (12)	0.0517 (10)	−0.0014 (8)	−0.0136 (7)	−0.0025 (9)
C9	0.0412 (9)	0.0826 (14)	0.0587 (11)	0.0084 (10)	−0.0137 (8)	−0.0201 (11)
C10	0.0642 (13)	0.105 (2)	0.0580 (12)	−0.0193 (13)	0.0066 (10)	−0.0134 (13)
C11	0.0814 (19)	0.180 (4)	0.0665 (16)	−0.037 (2)	0.0193 (14)	−0.0270 (19)
C12	0.0559 (15)	0.242 (6)	0.091 (2)	0.008 (2)	−0.0006 (16)	−0.072 (3)
C13	0.081 (2)	0.199 (5)	0.109 (3)	0.072 (3)	−0.0315 (19)	−0.079 (3)
C14	0.0873 (18)	0.120 (3)	0.0855 (18)	0.0499 (18)	−0.0337 (14)	−0.0394 (18)
C15	0.0591 (11)	0.0524 (11)	0.0557 (11)	0.0122 (9)	−0.0141 (9)	0.0009 (9)
C16	0.0701 (13)	0.0646 (14)	0.0509 (11)	0.0033 (11)	−0.0047 (9)	−0.0010 (9)
C17	0.096 (2)	0.085 (2)	0.0740 (15)	−0.0153 (16)	−0.0011 (14)	0.0102 (14)
C18	0.0803 (18)	0.121 (3)	0.0814 (18)	−0.0209 (18)	0.0020 (15)	0.0108 (17)
C19	0.0579 (13)	0.133 (3)	0.0741 (15)	0.0003 (16)	0.0015 (11)	−0.0062 (17)
C20	0.0598 (13)	0.0883 (16)	0.0596 (12)	0.0155 (12)	−0.0038 (10)	−0.0032 (11)
C21	0.0579 (11)	0.0641 (12)	0.0452 (10)	0.0074 (10)	−0.0061 (8)	−0.0054 (8)
N1	0.0555 (9)	0.0508 (9)	0.0507 (8)	0.0136 (8)	−0.0126 (7)	−0.0029 (7)
N2	0.0714 (11)	0.0535 (10)	0.0612 (10)	0.0123 (9)	−0.0106 (9)	0.0077 (8)
O1	0.0585 (8)	0.0495 (8)	0.0668 (8)	0.0097 (6)	−0.0270 (7)	−0.0065 (6)
O2	0.0412 (6)	0.0570 (8)	0.0582 (7)	0.0047 (6)	−0.0037 (6)	0.0086 (6)
O3	0.0774 (10)	0.0606 (9)	0.0751 (10)	−0.0004 (8)	−0.0123 (8)	0.0153 (8)
Cu1	0.05087 (19)	0.04200 (18)	0.04936 (19)	0.01286 (14)	−0.01906 (13)	−0.00646 (13)

Geometric parameters (Å, º) top

C1—O2	1.240 (2)	C13—C14	1.418 (5)
C1—O1	1.270 (2)	C13—H13	0.93
C1—C2	1.497 (2)	C14—H14	0.93
C2—C3	1.385 (3)	C15—N2	1.323 (3)
C2—C7	1.393 (3)	C15—N1	1.329 (2)
C3—C4	1.384 (3)	C15—H15	0.93
C3—H3	0.93	C16—N2	1.379 (3)
C4—C5	1.373 (4)	C16—C17	1.384 (4)
C4—H4	0.93	C16—C21	1.393 (3)
C5—C6	1.371 (3)	C17—C18	1.371 (4)
C5—H5	0.93	C17—H17	0.93
C6—C7	1.392 (3)	C18—C19	1.388 (5)
C6—H6	0.93	C18—H18	0.93
C7—C8	1.499 (3)	C19—C20	1.379 (4)
C8—O3	1.207 (2)	C19—H19	0.93
C8—C9	1.494 (3)	C20—C21	1.396 (3)
C9—C10	1.385 (4)	C20—H20	0.93
C9—C14	1.390 (4)	C21—N1	1.402 (3)
C10—C11	1.386 (4)	N1—Cu1	1.9916 (17)
C10—H10	0.93	N2—H2	0.86
C11—C12	1.355 (6)	O1—Cu1	1.9474 (13)
C11—H11	0.93	Cu1—O1ⁱ	1.9474 (13)
C12—C13	1.342 (6)	Cu1—N1ⁱ	1.9916 (17)
C12—H12	0.93

O2—C1—O1	124.26 (16)	C14—C13—H13	119.9
O2—C1—C2	119.54 (16)	C9—C14—C13	118.3 (4)
O1—C1—C2	116.20 (16)	C9—C14—H14	120.8
C3—C2—C7	119.45 (17)	C13—C14—H14	120.8
C3—C2—C1	120.21 (18)	N2—C15—N1	113.00 (19)
C7—C2—C1	120.32 (16)	N2—C15—H15	123.5
C4—C3—C2	120.5 (2)	N1—C15—H15	123.5
C4—C3—H3	119.8	N2—C16—C17	131.2 (2)
C2—C3—H3	119.8	N2—C16—C21	105.5 (2)
C5—C4—C3	120.0 (2)	C17—C16—C21	123.3 (2)
C5—C4—H4	120.0	C18—C17—C16	116.5 (3)
C3—C4—H4	120.0	C18—C17—H17	121.7
C6—C5—C4	120.1 (2)	C16—C17—H17	121.7
C6—C5—H5	120.0	C17—C18—C19	121.0 (3)
C4—C5—H5	120.0	C17—C18—H18	119.5
C5—C6—C7	120.8 (2)	C19—C18—H18	119.5
C5—C6—H6	119.6	C20—C19—C18	122.8 (3)
C7—C6—H6	119.6	C20—C19—H19	118.6
C6—C7—C2	119.15 (18)	C18—C19—H19	118.6
C6—C7—C8	117.45 (18)	C19—C20—C21	116.8 (3)
C2—C7—C8	123.33 (15)	C19—C20—H20	121.6
O3—C8—C9	122.7 (2)	C21—C20—H20	121.6
O3—C8—C7	119.97 (18)	C16—C21—C20	119.5 (2)
C9—C8—C7	117.12 (18)	C16—C21—N1	108.72 (18)
C10—C9—C14	119.9 (2)	C20—C21—N1	131.7 (2)
C10—C9—C8	121.3 (2)	C15—N1—C21	104.72 (17)
C14—C9—C8	118.7 (3)	C15—N1—Cu1	120.13 (15)
C9—C10—C11	119.9 (3)	C21—N1—Cu1	134.28 (13)
C9—C10—H10	120.1	C15—N2—C16	108.04 (17)
C11—C10—H10	120.1	C15—N2—H2	126.0
C12—C11—C10	120.0 (4)	C16—N2—H2	126.0
C12—C11—H11	120.0	C1—O1—Cu1	114.74 (12)
C10—C11—H11	120.0	O1—Cu1—O1ⁱ	180.0
C13—C12—C11	121.8 (3)	O1—Cu1—N1ⁱ	91.04 (6)
C13—C12—H12	119.1	O1ⁱ—Cu1—N1ⁱ	88.96 (6)
C11—C12—H12	119.1	O1—Cu1—N1	88.96 (6)
C12—C13—C14	120.1 (4)	O1ⁱ—Cu1—N1	91.04 (6)
C12—C13—H13	119.9	N1ⁱ—Cu1—N1	180.00 (5)

O2—C1—C2—C3	156.78 (19)	C12—C13—C14—C9	0.8 (5)
O1—C1—C2—C3	−23.2 (3)	N2—C16—C17—C18	178.5 (3)
O2—C1—C2—C7	−21.7 (2)	C21—C16—C17—C18	−0.3 (4)
O1—C1—C2—C7	158.32 (17)	C16—C17—C18—C19	−0.5 (4)
C7—C2—C3—C4	0.7 (3)	C17—C18—C19—C20	0.6 (5)
C1—C2—C3—C4	−177.8 (2)	C18—C19—C20—C21	0.0 (4)
C2—C3—C4—C5	−1.5 (4)	N2—C16—C21—C20	−178.15 (19)
C3—C4—C5—C6	1.6 (4)	C17—C16—C21—C20	0.9 (3)
C4—C5—C6—C7	−0.8 (4)	N2—C16—C21—N1	0.6 (2)
C5—C6—C7—C2	0.1 (3)	C17—C16—C21—N1	179.7 (2)
C5—C6—C7—C8	−177.1 (2)	C19—C20—C21—C16	−0.8 (3)
C3—C2—C7—C6	0.0 (3)	C19—C20—C21—N1	−179.2 (2)
C1—C2—C7—C6	178.49 (17)	N2—C15—N1—C21	−0.1 (2)
C3—C2—C7—C8	176.95 (18)	N2—C15—N1—Cu1	−170.88 (13)
C1—C2—C7—C8	−4.6 (3)	C16—C21—N1—C15	−0.3 (2)
C6—C7—C8—O3	98.0 (2)	C20—C21—N1—C15	178.2 (2)
C2—C7—C8—O3	−79.0 (2)	C16—C21—N1—Cu1	168.53 (14)
C6—C7—C8—C9	−77.5 (2)	C20—C21—N1—Cu1	−12.9 (3)
C2—C7—C8—C9	105.5 (2)	N1—C15—N2—C16	0.5 (2)
O3—C8—C9—C10	175.5 (2)	C17—C16—N2—C15	−179.6 (2)
C7—C8—C9—C10	−9.2 (3)	C21—C16—N2—C15	−0.7 (2)
O3—C8—C9—C14	−5.8 (3)	O2—C1—O1—Cu1	5.1 (2)
C7—C8—C9—C14	169.59 (19)	C2—C1—O1—Cu1	−174.87 (11)
C14—C9—C10—C11	−0.3 (4)	C1—O1—Cu1—N1ⁱ	77.26 (14)
C8—C9—C10—C11	178.4 (2)	C1—O1—Cu1—N1	−102.74 (14)
C9—C10—C11—C12	−0.1 (4)	C15—N1—Cu1—O1	−26.68 (15)
C10—C11—C12—C13	1.0 (5)	C21—N1—Cu1—O1	165.80 (18)
C11—C12—C13—C14	−1.3 (6)	C15—N1—Cu1—O1ⁱ	153.32 (15)
C10—C9—C14—C13	0.0 (4)	C21—N1—Cu1—O1ⁱ	−14.20 (18)
C8—C9—C14—C13	−178.8 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱⁱ	0.86	1.90	2.747 (2)	169 (2)
C5—H5···Cg1ⁱⁱⁱ	0.93	2.67	3.560 (2)	160 (2)
C11—H11···Cg2^iv	0.93	2.95	3.760 (2)	146 (2)

Symmetry codes: (ii) x, y−1, z; (iii) −x, y+1/2, −z+1/2; (iv) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₄H₉O₃)₂(C₇H₆N₂)₂]
M_r	750.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.8692 (6), 7.4521 (3), 23.0874 (15)
β (°)	95.111 (5)
V (Å³)	1862.61 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.64
Crystal size (mm)	0.41 × 0.39 × 0.23

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.550, 0.792
No. of measured, independent and observed [I > 2σ(I)] reflections	10706, 3859, 2987
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.103, 1.05
No. of reflections	3859
No. of parameters	241
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.43

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

C1—O2	1.240 (2)	N1—Cu1	1.9916 (17)
C1—O1	1.270 (2)	O1—Cu1	1.9474 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.86	1.90	2.747 (2)	169 (2)
C5—H5···Cg1ⁱⁱ	0.93	2.67	3.560 (2)	160 (2)
C11—H11···Cg2ⁱⁱⁱ	0.93	2.95	3.760 (2)	146 (2)

Symmetry codes: (i) x, y−1, z; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, y−1/2, −z+1/2.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for use of the Stoe IPDS II diffractometer (purchased under grant No. F279 of the University Research Fund).

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