catena-Poly[[di­aqua­bis­(4-formyl­benzoato-κO1)copper(II)]-μ-pyrazine-κ2N:N′]

Çelik, F.; Dilek, N.; Çaylak Delibaş, N.; Necefoğlu, H.; Hökelek, T.

doi:10.1107/S1600536813032297

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 1| January 2014| Pages m4-m5

https://doi.org/10.1107/S1600536813032297

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catena-Poly[[diaquabis(4-formylbenzoato-κO¹)copper(II)]-μ-pyrazine-κ²N:N′]

Fatih Çelik,^a Nefise Dilek,^b Nagihan Çaylak Delibaş,^c Hacali Necefoğlu ^a and Tuncer Hökelek ^d ^*

^aDepartment of Chemistry, Kafkas University, 36100 Kars, Turkey, ^bAksaray University, Department of Physics, 68100 Aksaray, Turkey, ^cDepartment of Physics, Sakarya University, 54187 Esentepe, Sakarya, Turkey, and ^dDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 18 November 2013; accepted 27 November 2013; online 7 December 2013)

In the title polymeric compound, [Cu(C₈H₅O₃)₂(C₄H₄N₂)(H₂O)₂]_n, the Cu^II atom is located on a twofold rotation axis and has a slightly distorted octahedral coordination sphere. In the equatorial plane, it is coordinated by two carboxylate O atoms of two symmetry-related monodentate formylbenzoate anions and by two N atoms of the bridging pyrazine ligand, which is bisected by the twofold rotation axis. The axial positions are occupied by two O atoms of the coordinating water molecules. In the formylbenzoate anion, the carboxylate group is twisted away from the attached benzene ring by 6.2 (2)°, while the benzene and pyrazine rings are oriented at a dihedral angle of 68.91 (8)°. The pyrazine ligands bridge the Cu^II cations, forming polymeric chains running along the b-axis direction. Strong intramolecular O—H⋯O hydrogen bonds link the water molecules to the carboxylate O atoms. In the crystal, O—H_water⋯O_water hydrogen bonds link adjacent chains into layers parallel to the bc plane. The layers are linked via C—H_pyrazine⋯O_formyl hydrogen bonds, forming a three-dimensional network. There are also weak C—H⋯π interactions present.

CCDC reference: 973941

Related literature

For structural functions and coordination relationships of arylcarboxylate ions in transition metal complexes of benzoic acid derivatives, see: Nadzhafov et al. (1981 ); Shnulin et al. (1981 ). For applications of transition metal complexes with biochemical molecules in biological systems, see: Antolini et al. (1982 ). Some benzoic acid derivatives, such as 4-aminobenzoic acid, have been extensively reported in coordination chemistry, as bifunctional organic ligands, due to the variety of their coordination modes, see: Chen & Chen (2002 ); Amiraslanov et al. (1979 ); Hauptmann et al. (2000 ). For a related structure involving 4-formylbenzoate, see: Hökelek et al. (2009 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

[Cu(C₈H₅O₃)₂(C₄H₄N₂)(H₂O)₂]
M_r = 477.90
Monoclinic, C 2/c
a = 21.7514 (4) Å
b = 6.8794 (2) Å
c = 12.9048 (3) Å
β = 93.621 (3)°
V = 1927.17 (8) Å³
Z = 4
Mo Kα radiation
μ = 1.19 mm⁻¹
T = 294 K
0.42 × 0.22 × 0.13 mm

Data collection

Bruker SMART BREEZE CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2012 ) T_min = 0.738, T_max = 0.857
14917 measured reflections
2398 independent reflections
2231 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.089
S = 1.14
2398 reflections
150 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H42⋯O2	0.80 (2)	1.86 (2)	2.640 (2)	163 (3)
O4—H41⋯O4ⁱ	0.79 (2)	2.41 (3)	2.778 (2)	110 (3)
C9—H9⋯O3ⁱⁱ	0.93	2.49	3.335 (3)	152
C7—H7⋯Cgⁱⁱⁱ	0.93	2.66	3.433 (2)	141
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+{\script{3\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT; 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, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 973941

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813032297/su2669sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813032297/su2669Isup2.hkl

checkCIF report

Comment top

The structural functions and coordination relationships of the arylcarboxylate ion in transition metal complexes of benzoic acid derivatives change depending on the nature and position of the substituent groups on the benzene ring, the nature of the additional ligand molecule or solvent, and the medium of the synthesis (Nadzhafov et al., 1981; Shnulin et al., 1981). Transition metal complexes with biochemically active ligands frequently show interesting physical and/or chemical properties, as a result they may find applications in biological systems (Antolini et al., 1982). Some benzoic acid derivatives, such as 4-aminobenzoic acid, have been extensively reported in coordination chemistry, as bifunctional organic ligands, due to the varieties of their coordination modes (Chen & Chen, 2002; Amiraslanov et al., 1979; Hauptmann et al., 2000). The title compound was synthesized and its crystal structure is reported herein.

The asymmetric unit of the title compound contains half a Cu^II ion, one formylbenzoate (FB) anion, one water molecule and half of a pyrazine molecule. Atoms Cu1, and N1 and N2 of the pyrazine ligand, are located on a two-fold rotation axis (Fig. 1). The pyrazine ligands bridge adjacent Cu^II ions forming polymeric chains running along the b-axis direction (Fig. 2). The distances between the symmetry related Cu^II ions [Cu1···Cu1ⁱ; symmetry code (i) = x, y-1, z] is 6.879 (3) Å.

In the equatorial plane of the Cu^II coordination sphere is compossed of two carboxylate O atoms (O1 and O1ⁱⁱ; symmetry code: (ii) -x+1, y, -z+0.5) of two symmtery related monodentate formylbenzoate anions and two N atoms (N1 and N2ⁱ) of the bridging pyrazine ligand, which is bisected by the two-fold rotation axis. The axial positions are occupied by two O atoms (O4 and O4ⁱⁱ) of the coordinated water molecules.

The near equality of the C1—O1 [1.278 (2) Å] and C1—O2 [1.234 (2) Å] bonds in the carboxylate group indicate a delocalized bonding arrangement, rather than localized single and double bonds. The average Cu—N bond length is 2.0497 (19) Å, while the Cu—O bond lengths are 1.9546 (12) Å (for benzoate oxygen O1) and 2.4768 (12) Å (for water oxygen O4), close to standard values (Allen et al., 1987). The dihedral angle between the planar carboxylate group (O1/C1/O2) and the adjacent benzene ring (C2—C7) is 6.2 (2)°, while the benzene and pyrazine rings are oriented at a dihedral angle of 68.91 (8)°. Strong intramolecular O—H···O hydrogen bonds (Table 1) link the water molecules to the carboxylate oxygens.

In the crystal, O-H_water···O_water hydrogen bonds (Table 1) link adjacent chains into layers parallel to the bc plane. The layes are linked via C—H_pyrazine···O_formyl hydrogen bonds forming a three-dimensional network. There also weak C—H···π interactions present.

Related literature top

For structural functions and coordination relationships of arylcarboxylate ions in transition metal complexes of benzoic acid derivatives, see: Nadzhafov et al. (1981); Shnulin et al. (1981). For applications of transition metal complexes with biochemical molecules in biological systems, see: Antolini et al. (1982). Some benzoic acid derivatives, such as 4-aminobenzoic acid, have been extensively reported in coordination chemistry, as bifunctional organic ligands, due to the variety of their coordination modes, see: Chen & Chen (2002); Amiraslanov et al. (1979); Hauptmann et al. (2000). For a related structure involving 4-formylbenzoate, see: Hökelek et al. (2009). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by the reaction of CuSO₄.5H₂O (1.25 g, 5 mmol) in H₂O (250 ml) and pyrazine (0.40 g, 5 mmol) in H₂O (30 ml) with sodium 4-formylbenzoate (1.72 g, 10 mmol) in H₂O (100 ml) at room temperature. The mixture was filtered and set aside to crystallize at ambient temperature for several days, giving blue block-like crystals.

Structure description top

For structural functions and coordination relationships of arylcarboxylate ions in transition metal complexes of benzoic acid derivatives, see: Nadzhafov et al. (1981); Shnulin et al. (1981). For applications of transition metal complexes with biochemical molecules in biological systems, see: Antolini et al. (1982). Some benzoic acid derivatives, such as 4-aminobenzoic acid, have been extensively reported in coordination chemistry, as bifunctional organic ligands, due to the variety of their coordination modes, see: Chen & Chen (2002); Amiraslanov et al. (1979); Hauptmann et al. (2000). For a related structure involving 4-formylbenzoate, see: Hökelek et al. (2009). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); 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, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of the coordination geometry around the Cu^II atom of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. The two-fold rotation axis bisects atoms Cu1, N1 and N2.
	Fig. 2. A partial view along the c axis of the crystal packing of the title compound.

catena-Poly[[diaquabis(4-formylbenzoato-κO¹)copper(II)]-µ-pyrazine-κ²N:N'] top

Crystal data top

[Cu(C₈H₅O₃)₂(C₄H₄N₂)(H₂O)₂]	F(000) = 980
M_r = 477.90	D_x = 1.647 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9971 reflections
a = 21.7514 (4) Å	θ = 2.4–28.4°
b = 6.8794 (2) Å	µ = 1.19 mm⁻¹
c = 12.9048 (3) Å	T = 294 K
β = 93.621 (3)°	Block, blue
V = 1927.17 (8) Å³	0.42 × 0.22 × 0.13 mm
Z = 4

Data collection top

Bruker SMART BREEZE CCD diffractometer	2398 independent reflections
Radiation source: fine-focus sealed tube	2231 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
φ and ω scans	θ_max = 28.4°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −28→27
T_min = 0.738, T_max = 0.857	k = −8→9
14917 measured reflections	l = −17→17

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ²(F_o²) + (0.0478P)² + 1.6638P] where P = (F_o² + 2F_c²)/3
2398 reflections	(Δ/σ)_max = 0.001
150 parameters	Δρ_max = 0.47 e Å⁻³
2 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Cu(C₈H₅O₃)₂(C₄H₄N₂)(H₂O)₂]	V = 1927.17 (8) Å³
M_r = 477.90	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 21.7514 (4) Å	µ = 1.19 mm⁻¹
b = 6.8794 (2) Å	T = 294 K
c = 12.9048 (3) Å	0.42 × 0.22 × 0.13 mm
β = 93.621 (3)°

Data collection top

Bruker SMART BREEZE CCD diffractometer	2398 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2012)	2231 reflections with I > 2σ(I)
T_min = 0.738, T_max = 0.857	R_int = 0.029
14917 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	2 restraints
wR(F²) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	Δρ_max = 0.47 e Å⁻³
2398 reflections	Δρ_min = −0.30 e Å⁻³
150 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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 > 2sigma(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
Cu1	0.50000	0.56167 (4)	0.25000	0.0226 (1)
O1	0.58159 (6)	0.55545 (17)	0.19469 (11)	0.0283 (3)
O2	0.63771 (7)	0.6755 (3)	0.33131 (11)	0.0478 (5)
O3	0.90018 (8)	0.6186 (4)	0.03875 (15)	0.0643 (7)
O4	0.54054 (7)	0.5818 (3)	0.43338 (12)	0.0429 (5)
N1	0.50000	0.8590 (3)	0.25000	0.0222 (5)
N2	0.50000	1.2632 (3)	0.25000	0.0228 (5)
C1	0.63185 (7)	0.6123 (2)	0.24173 (13)	0.0255 (4)
C2	0.68848 (7)	0.5984 (2)	0.18010 (13)	0.0233 (4)
C3	0.68624 (8)	0.5098 (3)	0.08295 (13)	0.0278 (4)
C4	0.73941 (8)	0.4934 (3)	0.02948 (13)	0.0311 (5)
C5	0.79501 (8)	0.5656 (3)	0.07299 (15)	0.0298 (5)
C6	0.79729 (8)	0.6554 (3)	0.16972 (14)	0.0322 (5)
C7	0.74435 (8)	0.6718 (3)	0.22284 (13)	0.0286 (5)
C8	0.85122 (10)	0.5472 (3)	0.01458 (19)	0.0433 (7)
C9	0.52244 (8)	0.9602 (2)	0.17228 (13)	0.0263 (5)
C10	0.52268 (8)	1.1618 (2)	0.17257 (13)	0.0265 (5)
H3	0.64910	0.46150	0.05390	0.0330*
H4	0.73790	0.43420	−0.03540	0.0370*
H6	0.83440	0.70420	0.19860	0.0390*
H7	0.74590	0.73200	0.28750	0.0340*
H8	0.84820	0.47380	−0.04600	0.0520*
H9	0.53820	0.89410	0.11700	0.0310*
H10	0.53900	1.22800	0.11770	0.0320*
H41	0.5464 (15)	0.485 (3)	0.465 (2)	0.065 (10)*
H42	0.5738 (10)	0.609 (5)	0.414 (2)	0.064 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0165 (2)	0.0139 (2)	0.0382 (2)	0.0000	0.0076 (1)	0.0000
O1	0.0170 (5)	0.0258 (6)	0.0428 (7)	−0.0016 (4)	0.0076 (5)	−0.0036 (5)
O2	0.0327 (7)	0.0712 (11)	0.0413 (8)	−0.0153 (7)	0.0155 (6)	−0.0173 (7)
O3	0.0307 (8)	0.0990 (15)	0.0650 (11)	−0.0003 (9)	0.0176 (7)	0.0074 (11)
O4	0.0330 (8)	0.0558 (10)	0.0408 (8)	−0.0057 (7)	0.0086 (6)	0.0119 (7)
N1	0.0214 (8)	0.0149 (9)	0.0308 (9)	0.0000	0.0065 (7)	0.0000
N2	0.0206 (8)	0.0160 (8)	0.0322 (9)	0.0000	0.0055 (7)	0.0000
C1	0.0211 (7)	0.0212 (7)	0.0350 (8)	−0.0011 (6)	0.0079 (6)	0.0000 (6)
C2	0.0186 (7)	0.0219 (7)	0.0298 (8)	0.0006 (6)	0.0046 (6)	0.0021 (6)
C3	0.0215 (7)	0.0302 (8)	0.0316 (8)	−0.0002 (6)	0.0002 (6)	−0.0008 (7)
C4	0.0312 (9)	0.0340 (9)	0.0284 (8)	0.0045 (7)	0.0045 (7)	−0.0018 (7)
C5	0.0236 (8)	0.0307 (9)	0.0359 (9)	0.0038 (6)	0.0093 (7)	0.0044 (7)
C6	0.0204 (7)	0.0372 (10)	0.0391 (9)	−0.0049 (7)	0.0032 (6)	0.0000 (8)
C7	0.0245 (8)	0.0312 (9)	0.0305 (8)	−0.0054 (7)	0.0044 (6)	−0.0046 (7)
C8	0.0317 (10)	0.0525 (14)	0.0475 (11)	0.0065 (8)	0.0170 (9)	0.0027 (9)
C9	0.0301 (8)	0.0206 (8)	0.0293 (8)	0.0001 (6)	0.0114 (6)	−0.0016 (6)
C10	0.0298 (8)	0.0200 (8)	0.0308 (8)	0.0006 (6)	0.0111 (6)	0.0029 (6)

Geometric parameters (Å, º) top

Cu1—O1	1.9547 (13)	C2—C3	1.392 (2)
Cu1—O4	2.4766 (15)	C2—C7	1.397 (2)
Cu1—N1	2.046 (2)	C3—C4	1.388 (2)
Cu1—N2ⁱ	2.053 (2)	C4—C5	1.392 (3)
Cu1—O1ⁱⁱ	1.9547 (13)	C5—C6	1.391 (3)
Cu1—O4ⁱⁱ	2.4766 (15)	C5—C8	1.482 (3)
O1—C1	1.278 (2)	C6—C7	1.381 (2)
O2—C1	1.234 (2)	C9—C10	1.3869 (19)
O3—C8	1.196 (3)	C3—H3	0.9300
O4—H42	0.80 (2)	C4—H4	0.9300
O4—H41	0.79 (2)	C6—H6	0.9300
N1—C9ⁱⁱ	1.3382 (19)	C7—H7	0.9300
N1—C9	1.3382 (19)	C8—H8	0.9300
N2—C10	1.3382 (19)	C9—H9	0.9300
N2—C10ⁱⁱ	1.3382 (19)	C10—H10	0.9300
C1—C2	1.511 (2)

O1—Cu1—O4	94.21 (5)	C3—C2—C7	119.60 (15)
O1—Cu1—N1	91.25 (4)	C1—C2—C7	119.15 (14)
O1—Cu1—N2ⁱ	88.75 (4)	C1—C2—C3	121.23 (14)
O1—Cu1—O1ⁱⁱ	177.49 (5)	C2—C3—C4	120.02 (16)
O1—Cu1—O4ⁱⁱ	85.93 (5)	C3—C4—C5	120.01 (16)
O4—Cu1—N1	86.80 (5)	C4—C5—C6	120.08 (16)
O4—Cu1—N2ⁱ	93.21 (5)	C4—C5—C8	119.21 (18)
O1ⁱⁱ—Cu1—O4	85.93 (5)	C6—C5—C8	120.71 (17)
O4—Cu1—O4ⁱⁱ	173.59 (7)	C5—C6—C7	119.87 (17)
N1—Cu1—N2ⁱ	180.00	C2—C7—C6	120.41 (16)
O1ⁱⁱ—Cu1—N1	91.25 (4)	O3—C8—C5	125.6 (2)
O4ⁱⁱ—Cu1—N1	86.80 (5)	N1—C9—C10	121.31 (16)
O1ⁱⁱ—Cu1—N2ⁱ	88.75 (4)	N2—C10—C9	121.45 (16)
O4ⁱⁱ—Cu1—N2ⁱ	93.21 (5)	C2—C3—H3	120.00
O1ⁱⁱ—Cu1—O4ⁱⁱ	94.21 (5)	C4—C3—H3	120.00
Cu1—O1—C1	126.09 (12)	C3—C4—H4	120.00
Cu1—O4—H41	119.0 (18)	C5—C4—H4	120.00
Cu1—O4—H42	89.4 (18)	C5—C6—H6	120.00
H41—O4—H42	104 (3)	C7—C6—H6	120.00
C9—N1—C9ⁱⁱ	117.30 (18)	C2—C7—H7	120.00
Cu1—N1—C9	121.35 (10)	C6—C7—H7	120.00
Cu1—N1—C9ⁱⁱ	121.35 (10)	O3—C8—H8	117.00
Cu1ⁱⁱⁱ—N2—C10	121.42 (10)	C5—C8—H8	117.00
C10—N2—C10ⁱⁱ	117.16 (18)	N1—C9—H9	119.00
Cu1ⁱⁱⁱ—N2—C10ⁱⁱ	121.42 (10)	C10—C9—H9	119.00
O1—C1—O2	125.98 (16)	N2—C10—H10	119.00
O2—C1—C2	118.42 (15)	C9—C10—H10	119.00
O1—C1—C2	115.60 (14)

O4—Cu1—O1—C1	−20.13 (13)	O1—C1—C2—C7	174.99 (15)
N1—Cu1—O1—C1	66.75 (12)	O2—C1—C2—C3	173.20 (18)
N2ⁱ—Cu1—O1—C1	−113.26 (12)	O2—C1—C2—C7	−5.2 (2)
O4ⁱⁱ—Cu1—O1—C1	153.44 (13)	C1—C2—C3—C4	−177.90 (16)
O1—Cu1—N1—C9	39.77 (10)	C7—C2—C3—C4	0.5 (3)
O1—Cu1—N1—C9ⁱⁱ	−140.23 (10)	C1—C2—C7—C6	177.88 (16)
O4—Cu1—N1—C9	133.92 (9)	C3—C2—C7—C6	−0.6 (3)
O4—Cu1—N1—C9ⁱⁱ	−46.08 (9)	C2—C3—C4—C5	0.0 (3)
O1ⁱⁱ—Cu1—N1—C9	−140.23 (10)	C3—C4—C5—C6	−0.4 (3)
O4ⁱⁱ—Cu1—N1—C9	−46.08 (9)	C3—C4—C5—C8	−179.83 (19)
Cu1—O1—C1—O2	2.3 (2)	C4—C5—C6—C7	0.4 (3)
Cu1—O1—C1—C2	−177.93 (9)	C8—C5—C6—C7	179.77 (19)
Cu1—N1—C9—C10	−179.70 (12)	C4—C5—C8—O3	172.6 (2)
C9ⁱⁱ—N1—C9—C10	0.3 (2)	C6—C5—C8—O3	−6.8 (4)
Cu1ⁱⁱⁱ—N2—C10—C9	−179.70 (12)	C5—C6—C7—C2	0.1 (3)
C10ⁱⁱ—N2—C10—C9	0.3 (2)	N1—C9—C10—N2	−0.6 (2)
O1—C1—C2—C3	−6.6 (2)

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

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O4—H42···O2	0.80 (2)	1.86 (2)	2.640 (2)	163 (3)
O4—H41···O4^iv	0.79 (2)	2.41 (3)	2.778 (2)	110 (3)
C9—H9···O3^v	0.93	2.49	3.335 (3)	152
C7—H7···Cg^vi	0.93	2.66	3.433 (2)	141

Symmetry codes: (iv) −x+1, −y+1, −z+1; (v) −x+3/2, −y+3/2, −z; (vi) −x+3/2, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O4—H42···O2	0.80 (2)	1.86 (2)	2.640 (2)	163 (3)
O4—H41···O4ⁱ	0.79 (2)	2.41 (3)	2.778 (2)	110 (3)
C9—H9···O3ⁱⁱ	0.93	2.49	3.335 (3)	152
C7—H7···Cgⁱⁱⁱ	0.93	2.66	3.433 (2)	141

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3/2, −y+3/2, −z; (iii) −x+3/2, y+1/2, −z+1/2.

Acknowledgements

The authors acknowledge Aksaray University, Science and Technology Application and Research Center, Aksaray, Turkey, for the use of the Bruker SMART BREEZE CCD diffractometer (purchased under grant No. 2010K120480 of the State of Planning Organization). This work was supported financially by Kafkas University Research Fund (grant No. 2012-FEF-12).

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