Crystal structure of catena-poly[[bis­(acetato-κO)copper(II)]-bis­[μ-4-(1H-imidazol-1-yl)phenol]-κ2N3:O;κ2O:N3]

Poyraz, M.; Sarı, M.

doi:10.1107/S2056989017000780

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ISSN: 2056-9890

Volume 73| Part 2| February 2017| Pages 209-212

https://doi.org/10.1107/S2056989017000780

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Crystal structure of catena-poly[[bis(acetato-κO)copper(II)]-bis[μ-4-(1H-imidazol-1-yl)phenol]-κ²N³:O;κ²O:N³]

Mehmet Poyraz ^a ^* and Musa Sarı ^b

^aDepartment of Chemistry, Faculty of Science and Arts, Afyon Kocatepe University, TR-03200 Afyonkarahisar, Turkey, and ^bDepartment of Physics Education, Gazi University, Beşevler, TR-06500 Ankara, Turkey
^*Correspondence e-mail: poyraz@aku.edu.tr

Edited by M. Weil, Vienna University of Technology, Austria (Received 4 December 2016; accepted 16 January 2017; online 20 January 2017)

In the title compound, [Cu(CH₃COO)₂(C₉H₈N₂O)₂]_n, the Cu^II ion resides on a centre of inversion, displaying a tetragonally distorted octahedral coordination environment defined by two pairs of N and O atoms of symmetry-related 4-(1H-imidazol-1-yl)phenol ligands and the O atoms of two symmetry-related acetate ligands. The bridging mode of the 4-(1H-imidazol-1-yl)phenol ligands is associated with a very long Cu⋯O interactions involving the phenol O atom of the heterocyclic ligand, which creates chains extending parallel to [100]. In the crystal, the chains are arranged in a distorted hexagonal rod packing and are linked via C—H⋯O hydrogen bonds and by π–π stacking interactions involving centrosymmetrically related pairs of imidazole and phenol rings.

Keywords: crystal structure; polymeric structure; hydrogen bonds; copper(II); acetate; imidazole; π–π stacking.

CCDC reference: 1520352

1. Chemical context

Coordination polymers have been investigated as materials with interesting properties such as magnetism (Zhu et al., 2010 ), luminescence (Cui et al., 2012 ), catalysis (Wang et al., 2011 ) or absorption (Zhang et al., 2017 ). Some coordination polymers are also known to show photocatalytic activity with respect to the decomposition of organic dyes (Yang et al., 2010 ; Yin et al., 2015 ).

In the past few years, metal complexes with ligands derived from imidazole have attracted much attention, not only for their fascinating crystal structures, but also for their interesting applications related to antifungal (Rezaei et al., 2011 ), pesticidal (Stenersen et al., 2004 ) and plant-growth regulatory properties (Choi et al., 2010 ), or drugs in general (Lednicer et al., 1998 ; Adams et al., 2001 ). Most of these compounds exhibit typical molecular structures whereas the number of imidazole-based coordination polymers (Martins et al., 2010 ; Masciocchi et al., 2001 ; Stamatatos et al., 2009 ) is much lower, probably due to the difficulty of growing single crystals.

In this communication we report on the synthesis and crystal structure of a copper(II) coordination polymer, [Cu(CH₃COO)₂(C₉H₈N₂O)₂]_n, comprising 4-(1H-imidazol-1-yl)-phenol and acetate ligands.

2. Structural commentary

The asymmetric unit of the title compound comprises of one Cu^II atom, one 4-(1H-imidazol-1-yl)-phenol ligand and one acetate group, with the Cu^II atom situated on a crystallographic inversion centre. The distorted octahedral coordination environment of the Cu^II atom is defined by two symmetry-related pairs of imidazole N atoms and phenol O atoms from the heterocyclic ligands and by two O atoms of a symmetry-related pair of monodentate acetate ligands (Fig. 1). The Cu—O(acetate) [1.9322 (18) Å] and Cu—N(imidazole) [2.003 (2) Å] bonds are arranged in the equatorial plane and are within normal lengths (Ding et al., 2005 ; Song et al., 2008 ; Yun et al., 2008 ; Yu & Deng, 2011 ). The equatorial bond angles are in the range 86.94 (7)–93.06 (7)° in the Cu1N₂O₄ polyhedron (Table 1). The bond involving the phenolic O3 atom is very weak, with a distance of Cu⋯O = 2.739 (2) Å, completing the tetragonally distorted octahedron. The N,O-bridging character of the 4-(1H-imidazol-1-yl)-phenol ligand leads to the formation of chains extending parallel to [100], whereby the ligands are oriented in an antiparallel fashion within a chain. The dihedral angle between the imidazole group (N1,N2,C1–C3) and the phenyl ring (C4–C9) is 24.07 (2)°. An intrachain hydrogen bond between the phenol OH group (O3) and the non-coordinating carboxylate O atom (O1) of the acetate ligand is present (Table 2, Fig. 2).

Table 1
Selected geometric parameters (Å, °)

N1—Cu1	2.003 (2)	O3—Cu1ⁱ	2.739 (2)
Cu1—O2	1.9322 (18)

O2—Cu1—N1	90.56 (8)	N1—Cu1—O3ⁱⁱⁱ	91.31 (7)
N1—Cu1—N1ⁱⁱ	180.0	O2—Cu1—O3^iv	86.94 (7)
O2—Cu1—O3ⁱⁱⁱ	93.06 (7)	N1—Cu1—O3^iv	88.69 (7)
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y+1, -z+1; (iii) -x+1, -y+1, -z+1; (iv) x+1, y, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1^v	0.95	2.44	3.356 (3)	161
O3—H3A⋯O1ⁱⁱⁱ	0.84	1.80	2.637 (3)	172
Symmetry codes: (iii) -x+1, -y+1, -z+1; (v) x, y, z+1.

Figure 1
The coordination environment of the Cu^II atom in the title compound. Displacement ellipsoids are drawn at the 30% probability level; non-labelled atoms are related to labelled atoms by (−x + 1, −y + 1, −z).

Figure 2
The crystal structure of the title compound showing the formation of chains extending parallel to [100]. Hydrogen-bonding interactions are shown as dashed lines.

3. Supramolecular features

In the crystal, the chains are aligned in a distorted hexagonal rod packing perpendicular to the chain direction. Chains are linked through intermolecular C—H⋯O interactions between a phenyl CH group and the non-coordinating carboxylate O atom (O1) that consequently acts as a double acceptor atom (Fig. 2, Table 2). Additional π–π stacking interactions involving centrosymmetrically related pairs of imidazole and phenol rings, with the shortest distance between an N atom and a C atom being 3.372 (2) Å, are also present. The interplanar angle between the two rings is 24.1 (1)°.

4. Database survey

The literature about one-dimensional inorganic–organic coordination polymers based on copper(II) complexes with Cu^II either in a square-pyramidal or a distorted octahedral coordination environment is vast. Just to take very recent examples, three such structures have been reported (Hazra et al., 2017 ; Puchoňová et al., 2017 ; Shaabani et al., 2017 ). Nevertheless, there is only limited research on 4-(1H-imidazol-1-yl)-phenol as a ligand (Maher et al., 1994 ; Wei et al., 2007 ; Yurdakul & Badoğlu, 2015 ). To the best of our knowledge, only one discrete copper(II) complex of 4-(1H-imidazol-1-yl)-phenol (Yu & Deng, 2011) has been reported. In this regard, the title compound is the first Cu^II coordination polymer with 4-(1H-imidazol-1-yl)-phenol.

5. Synthesis and crystallization

4-(1H-Imidazol-1-yl)phenol (0.0480 g, 0.3 mmol) was dissolved in 5 ml ethanol, a water solution (5 ml) of Na₂CO₃ (0.0318 g, 0.3 mmol) was slowly added, and an ethanol solution (5 ml) of Cu(NO₃)₂·2.5H₂O (0.0349 g, 0.15 mmol) was added slowly with stirring for 30 min. To the formed cloudy suspension, an aqueous solution of acetic acid (0.3 mmol) was added. The resulting solution turned to a transparent blue colour. After stirring for three h, the solution was allowed to evaporate at room temperature. A number of blue single crystals were obtained after a few days.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. C-bound H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with distances in the range 0.93–0.96Å and with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(C) for methyl atoms. The H atom of the phenol OH group was located in a difference map and was constrained at a distance of O—H = 0.84 Å and with U_iso(H) =1.5U_eq(O).

Table 3
Experimental details

Crystal data
Chemical formula	[Cu(C₂H₃O₂)₂(C₉H₈N₂O)₂]
M_r	501.99
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.2029 (15), 15.089 (2), 7.7814 (11)
β (°)	111.545 (4)
V (Å³)	1114.2 (3)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	1.03
Crystal size (mm)	0.11 × 0.09 × 0.07

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2013 )
T_min, T_max	0.895, 0.931
No. of measured, independent and observed [I > 2σ(I)] reflections	40729, 2784, 2156
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.100, 1.15
No. of reflections	2784
No. of parameters	153
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.30
Computer programs: APEX2 and SAINT (Bruker, 2013), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), Mercury (Macrae et al., 2008 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1520352

Crystal structure: contains datablocks I, Global. DOI: https://doi.org/10.1107/S2056989017000780/wm4035sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017000780/wm4035Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

catena-Poly[[bis(acetato-κO)copper(II)]-bis[µ-4-(1H-imidazol-1-yl)phenol]-κ²N³:O;κ²O:N³] top

Crystal data top

[Cu(C₂H₃O₂)₂(C₉H₈N₂O)₂]	F(000) = 518
M_r = 501.99	D_x = 1.496 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.2029 (15) Å	Cell parameters from 9911 reflections
b = 15.089 (2) Å	θ = 3.2–28.0°
c = 7.7814 (11) Å	µ = 1.03 mm⁻¹
β = 111.545 (4)°	T = 296 K
V = 1114.2 (3) Å³	Block, blue
Z = 2	0.11 × 0.09 × 0.07 mm

Data collection top

Bruker APEXII CCD diffractometer	2156 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.051
Absorption correction: multi-scan (SADABS; Bruker, 2013)	θ_max = 28.3°, θ_min = 3.1°
T_min = 0.895, T_max = 0.931	h = −13→13
40729 measured reflections	k = −20→20
2784 independent reflections	l = −10→10

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0249P)² + 1.2448P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max < 0.001
2784 reflections	Δρ_max = 0.26 e Å⁻³
153 parameters	Δρ_min = −0.30 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
C1	0.7431 (2)	0.55700 (18)	0.5692 (3)	0.0350 (5)
H1	0.7461	0.5059	0.6420	0.042*
C2	0.7933 (4)	0.6526 (2)	0.4009 (5)	0.0601 (9)
H2	0.8394	0.6819	0.3308	0.072*
C3	0.6778 (4)	0.6824 (2)	0.4266 (5)	0.0656 (10)
H3	0.6285	0.7359	0.3794	0.079*
C4	0.5265 (2)	0.62360 (16)	0.5918 (3)	0.0333 (5)
C5	0.5302 (3)	0.57796 (19)	0.7472 (4)	0.0408 (6)
H5	0.6125	0.5463	0.8195	0.049*
C6	0.4129 (3)	0.5787 (2)	0.7968 (4)	0.0430 (6)
H6	0.4149	0.5470	0.9033	0.052*
C7	0.2929 (2)	0.62494 (18)	0.6930 (3)	0.0370 (6)
C8	0.2926 (3)	0.67390 (18)	0.5434 (4)	0.0419 (6)
H8	0.2126	0.7087	0.4760	0.050*
C9	0.4084 (3)	0.67258 (18)	0.4912 (4)	0.0403 (6)
H9	0.4069	0.7053	0.3861	0.048*
C10	0.9356 (3)	0.56669 (19)	0.1300 (3)	0.0402 (6)
C11	0.9592 (4)	0.6405 (2)	0.0154 (4)	0.0617 (9)
H11A	0.9094	0.6273	−0.1159	0.093*
H11B	1.0603	0.6463	0.0408	0.093*
H11C	0.9234	0.6961	0.0464	0.093*
N1	0.8345 (2)	0.57396 (15)	0.4905 (3)	0.0368 (5)
N2	0.6450 (2)	0.62096 (14)	0.5338 (3)	0.0362 (5)
Cu1	1.0000	0.5000	0.5000	0.03750 (14)
O1	0.8401 (2)	0.51168 (15)	0.0597 (3)	0.0528 (5)
O2	1.01849 (18)	0.56716 (14)	0.2987 (2)	0.0455 (5)
O3	0.17326 (19)	0.62330 (15)	0.7320 (3)	0.0502 (5)
H3A	0.1775	0.5811	0.8043	0.075*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0274 (11)	0.0431 (14)	0.0347 (12)	−0.0002 (10)	0.0115 (9)	0.0037 (10)
C2	0.073 (2)	0.0432 (17)	0.089 (2)	0.0039 (15)	0.060 (2)	0.0134 (16)
C3	0.079 (2)	0.0395 (17)	0.104 (3)	0.0157 (16)	0.064 (2)	0.0252 (17)
C4	0.0288 (11)	0.0337 (12)	0.0384 (13)	−0.0008 (9)	0.0135 (10)	−0.0017 (10)
C5	0.0271 (12)	0.0540 (17)	0.0403 (13)	0.0071 (11)	0.0111 (10)	0.0107 (12)
C6	0.0345 (13)	0.0601 (18)	0.0369 (13)	0.0048 (12)	0.0161 (11)	0.0117 (12)
C7	0.0282 (11)	0.0441 (14)	0.0403 (13)	0.0003 (10)	0.0144 (10)	−0.0056 (11)
C8	0.0333 (13)	0.0411 (15)	0.0494 (15)	0.0096 (11)	0.0129 (11)	0.0067 (12)
C9	0.0380 (13)	0.0397 (14)	0.0440 (14)	0.0047 (11)	0.0159 (11)	0.0092 (11)
C10	0.0364 (13)	0.0524 (16)	0.0369 (13)	0.0142 (12)	0.0195 (11)	0.0071 (12)
C11	0.082 (2)	0.056 (2)	0.0539 (18)	0.0127 (17)	0.0328 (17)	0.0158 (15)
N1	0.0313 (10)	0.0428 (12)	0.0393 (11)	−0.0035 (9)	0.0165 (9)	−0.0029 (9)
N2	0.0333 (10)	0.0357 (11)	0.0435 (11)	0.0015 (9)	0.0187 (9)	0.0027 (9)
Cu1	0.0246 (2)	0.0589 (3)	0.0293 (2)	0.0002 (2)	0.01022 (15)	0.0018 (2)
O1	0.0430 (10)	0.0701 (14)	0.0416 (10)	0.0012 (10)	0.0112 (8)	0.0052 (10)
O2	0.0316 (9)	0.0717 (14)	0.0350 (9)	0.0000 (9)	0.0141 (8)	0.0087 (9)
O3	0.0339 (9)	0.0667 (14)	0.0571 (12)	0.0073 (9)	0.0253 (9)	0.0065 (10)

Geometric parameters (Å, º) top

C1—N1	1.315 (3)	C8—C9	1.383 (4)
C1—N2	1.345 (3)	C8—Cu1ⁱ	3.895 (3)
C1—Cu1	2.989 (2)	C8—H8	0.9500
C1—H1	0.9500	C9—H9	0.9500
C2—C3	1.343 (4)	C10—O1	1.244 (3)
C2—N1	1.361 (4)	C10—O2	1.274 (3)
C2—Cu1	3.024 (3)	C10—C11	1.501 (4)
C2—H2	0.9500	C10—Cu1	2.888 (3)
C3—N2	1.369 (4)	C11—H11A	0.9800
C3—H3	0.9500	C11—H11B	0.9800
C4—C5	1.380 (3)	C11—H11C	0.9800
C4—C9	1.385 (3)	N1—Cu1	2.003 (2)
C4—N2	1.438 (3)	Cu1—O2ⁱⁱ	1.9322 (18)
C5—C6	1.386 (3)	Cu1—O2	1.9322 (18)
C5—H5	0.9500	Cu1—N1ⁱⁱ	2.003 (2)
C6—C7	1.383 (4)	Cu1—O3ⁱⁱⁱ	2.739 (2)
C6—H6	0.9500	Cu1—O3^iv	2.739 (2)
C7—O3	1.363 (3)	O3—Cu1ⁱ	2.739 (2)
C7—C8	1.377 (4)	O3—H3A	0.8400
C7—Cu1ⁱ	3.383 (2)

N1—C1—N2	111.5 (2)	O1—C10—O2	125.0 (3)
N2—C1—Cu1	143.71 (17)	O1—C10—C11	120.3 (3)
N1—C1—H1	124.2	O2—C10—C11	114.7 (3)
N2—C1—H1	124.2	O1—C10—Cu1	93.50 (16)
Cu1—C1—H1	92.1	C11—C10—Cu1	145.5 (2)
C3—C2—N1	109.8 (3)	C10—C11—H11A	109.5
C3—C2—Cu1	141.7 (2)	C10—C11—H11B	109.5
C3—C2—H2	125.1	H11A—C11—H11B	109.5
N1—C2—H2	125.1	C10—C11—H11C	109.5
Cu1—C2—H2	93.2	H11A—C11—H11C	109.5
C2—C3—N2	106.8 (3)	H11B—C11—H11C	109.5
C2—C3—H3	126.6	C1—N1—C2	105.7 (2)
N2—C3—H3	126.6	C1—N1—Cu1	127.34 (18)
C5—C4—C9	120.0 (2)	C2—N1—Cu1	127.00 (18)
C5—C4—N2	120.4 (2)	C1—N2—C3	106.3 (2)
C9—C4—N2	119.6 (2)	C1—N2—C4	127.2 (2)
C4—C5—C6	119.4 (2)	C3—N2—C4	126.5 (2)
C4—C5—H5	120.3	O2ⁱⁱ—Cu1—O2	180.0
C6—C5—H5	120.3	O2ⁱⁱ—Cu1—N1	89.44 (8)
C7—C6—C5	120.7 (2)	O2—Cu1—N1	90.56 (8)
C7—C6—H6	119.6	O2ⁱⁱ—Cu1—N1ⁱⁱ	90.56 (8)
C5—C6—H6	119.6	O2—Cu1—N1ⁱⁱ	89.44 (8)
O3—C7—C8	118.3 (2)	N1—Cu1—N1ⁱⁱ	180.0
O3—C7—C6	122.3 (2)	O2ⁱⁱ—Cu1—O3ⁱⁱⁱ	86.94 (7)
C8—C7—C6	119.4 (2)	O2—Cu1—O3ⁱⁱⁱ	93.06 (7)
O3—C7—Cu1ⁱ	51.02 (13)	N1—Cu1—O3ⁱⁱⁱ	91.31 (7)
C8—C7—Cu1ⁱ	101.33 (16)	N1ⁱⁱ—Cu1—O3ⁱⁱⁱ	88.69 (7)
C6—C7—Cu1ⁱ	115.23 (18)	O2ⁱⁱ—Cu1—O3^iv	93.06 (7)
C7—C8—C9	120.2 (2)	O2—Cu1—O3^iv	86.94 (7)
C7—C8—Cu1ⁱ	58.39 (14)	N1—Cu1—O3^iv	88.69 (7)
C9—C8—Cu1ⁱ	132.43 (19)	N1ⁱⁱ—Cu1—O3^iv	91.31 (7)
C7—C8—H8	119.9	O3ⁱⁱⁱ—Cu1—O3^iv	180.00 (7)
C9—C8—H8	119.9	C10—O1—Cu1	63.78 (14)
Cu1ⁱ—C8—H8	81.3	C10—O2—Cu1	127.36 (18)
C8—C9—C4	120.1 (2)	C7—O3—Cu1ⁱ	106.23 (16)
C8—C9—H9	120.0	C7—O3—H3A	109.5
C4—C9—H9	120.0	Cu1ⁱ—O3—H3A	77.8

N1—C2—C3—N2	−0.4 (4)	C3—C2—N1—C1	0.1 (4)
Cu1—C2—C3—N2	−0.5 (6)	Cu1—C2—N1—C1	179.9 (3)
C9—C4—C5—C6	2.6 (4)	C3—C2—N1—Cu1	−179.8 (2)
N2—C4—C5—C6	−177.6 (3)	N1—C1—N2—C3	−0.4 (3)
C4—C5—C6—C7	−0.3 (4)	Cu1—C1—N2—C3	−0.5 (4)
C5—C6—C7—O3	176.5 (3)	N1—C1—N2—C4	177.9 (2)
C5—C6—C7—C8	−2.9 (4)	Cu1—C1—N2—C4	177.83 (19)
C5—C6—C7—Cu1ⁱ	118.1 (3)	C2—C3—N2—C1	0.5 (4)
O3—C7—C8—C9	−175.6 (3)	C2—C3—N2—C4	−177.9 (3)
C6—C7—C8—C9	3.8 (4)	C5—C4—N2—C1	25.2 (4)
Cu1ⁱ—C7—C8—C9	−123.9 (2)	C9—C4—N2—C1	−155.1 (3)
O3—C7—C8—Cu1ⁱ	−51.63 (19)	C5—C4—N2—C3	−156.8 (3)
C6—C7—C8—Cu1ⁱ	127.7 (3)	C9—C4—N2—C3	23.0 (4)
C7—C8—C9—C4	−1.5 (4)	O2—C10—O1—Cu1	6.7 (2)
Cu1ⁱ—C8—C9—C4	−74.7 (3)	C11—C10—O1—Cu1	−172.5 (3)
C5—C4—C9—C8	−1.7 (4)	O1—C10—O2—Cu1	−12.6 (4)
N2—C4—C9—C8	178.5 (2)	C11—C10—O2—Cu1	166.60 (19)
N2—C1—N1—C2	0.2 (3)	C8—C7—O3—Cu1ⁱ	81.4 (3)
Cu1—C1—N1—C2	−179.9 (3)	C6—C7—O3—Cu1ⁱ	−97.9 (3)
N2—C1—N1—Cu1	−179.88 (16)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1^v	0.95	2.44	3.356 (3)	161
O3—H3A···O1ⁱⁱⁱ	0.84	1.80	2.637 (3)	172

Symmetry codes: (iii) −x+1, −y+1, −z+1; (v) x, y, z+1.

Acknowledgements

The authors acknowledge Scientific and Technological Research Application and Research Center, Sinop University, Turkey, for the use of the Bruker D8 QUEST diffractometer and Dr Onur Şahin for help and guidance.

References

Adams, J. L., Boehm, J. C., Gallagher, T. F., Kassis, S., Webb, E. F., Hall, R., Sorenson, M., Garigipati, R., Griswold, D. E. & Lee, J. C. (2001). Bioorg. Med. Chem. Lett. 11, 2867–2870. CrossRef CAS Google Scholar
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, J. H., Abe, N., Tanaka, H., Fushimi, K., Nishina, Y., Morita, A., Kiriiwa, Y., Motohashi, R., Hashizume, D., Koshino, H. & Kawagishi, H. (2010). J. Agric. Food Chem. 58, 9956–9959. CSD CrossRef CAS Google Scholar
Cui, Y. J., Yue, Y. F., Qian, G. D. & Chen, B. L. (2012). Chem. Rev. 112, 1126–1162. Web of Science CrossRef CAS PubMed Google Scholar
Ding, C.-F., Zhang, S.-S., Tian, B.-Q., Li, X.-M., Xu, H. & Ouyang, P.-K. (2005). Acta Cryst. E61, m235–m236. CSD CrossRef IUCr Journals Google Scholar
Hazra, S., Martins, L. M. D. R. S., Guedes da Silva, M. F. C. & Pombeiro, A. J. L. (2017). Inorg. Chim. Acta, 455, 549–556. CSD CrossRef CAS Google Scholar
Lednicer, D. (1998). Drugs Based on Five-Membered Heterocycles, in Strategies for Organic Drug Synthesis and Design. New York: Wiley. Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Maher, J. P., McCleverty, J. A., Ward, M. D. & Wlodarczyk, A. (1994). J. Chem. Soc. Dalton Trans. pp. 143–147. CrossRef Google Scholar
Martins, G. A. V., Byrne, P. J., Allan, P., Teat, S. J., Slawin, A. M. Z., Li, Y. & Morris, R. E. (2010). Dalton Trans. 39, 1758–1762. Web of Science CrossRef CAS PubMed Google Scholar
Masciocchi, N., Bruni, S., Cariati, E., Cariati, F., Galli, S. & Sironi, A. (2001). Inorg. Chem. 40, 5897–5905. Web of Science CSD CrossRef PubMed CAS Google Scholar
Puchoňová, M., Švorec, J., Švorc, Ľ., Pavlik, J., Mazúr, M., Dlháň, Ľ., Růžičková, Z., Moncoľ, J. & Valigura, D. (2017). Inorg. Chim. Acta, 455, 298–306. Google Scholar
Rezaei, Z., Khabnadideh, S., Zomorodian, K., Pakshir, K., Kashi, G., Sanagoei, N. & Gholami, S. (2011). Arch. Pharm. Pharm. Med. Chem. 344, 658–665. CrossRef CAS Google Scholar
Shaabani, B., Rad-Yousefnia, N., Zahedi, M., Ertan, Ş., Blake, G. R. & Zakerhamidi, M. S. (2017). Inorg. Chim. Acta, 455, 158–165. CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Song, W.-D., Huang, X.-H. & Wang, H. (2008). Acta Cryst. E64, m764. CSD CrossRef IUCr Journals Google Scholar
Stamatatos, T. C., Perlepes, S. P., Raptopoulou, C. P., Terzis, A., Patrickios, C. S., Tasiopoulos, A. J. & Boudalis, A. K. (2009). Dalton Trans. pp. 3354–3362. CSD CrossRef Google Scholar
Stenersen, J. (2004). In Chemical Pesticides Mode of Action and Toxicology. Boca Raton: CRC Press. Google Scholar
Wang, S. J., Li, L., Zhang, J. Y., Yuan, X. C. & Su, C. Y. (2011). J. Mater. Chem. 21, 7098–7104. CSD CrossRef CAS Google Scholar
Wei, R. G., Adler, M., Davey, D., Ho, E., Mohan, R., Polokoff, R., Tseng, J.-L., Whitlow, M., Xu, W., Yuan, S. & Phillips, G. (2007). Bioorg. Med. Chem. Lett. 17, 2499–2504. CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, H. X., Liu, T. F., Cao, M. N., Li, H. F., Gao, S. Y. & Cao, R. (2010). Chem. Commun. 46, 2429–2431. CrossRef CAS Google Scholar
Yin, W.-Y., Huang, Z.-L., Tang, X.-Y., Wang, J., Cheng, H.-J., Ma, Y.-S., Yuan, R.-X. & Liu, D. (2015). New J. Chem. 39, 7130–7139. CSD CrossRef CAS Google Scholar
Yu, R.-J. & Deng, B. (2011). Acta Cryst. E67, m1253. CSD CrossRef IUCr Journals Google Scholar
Yun, R., Ying, W., Qi, B., Fan, X. & Wu, H. (2008). Acta Cryst. E64, m1529. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yurdakul, S. & Badoğlu, S. (2015). Spectrochim. Acta Part A, 150, 614–622. CrossRef CAS Google Scholar
Zhang, X., Wu, X. X., Guo, J. Z., Huo, J. H. & Ding, B. (2017). J. Mol. Struct. 1127, 183–190. CSD CrossRef CAS Google Scholar
Zhu, X., Zhao, J. W., Li, B. L., Song, Y., Zhang, Y. M. & Zhang, Y. (2010). Inorg. Chem. 49, 1266–1270. Web of Science CSD CrossRef CAS PubMed Google Scholar

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