Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 5| May 2015| Pages m112-m113
https://doi.org/10.1107/S205698901500729X

Crystal structure of di­chlorido­bis­­(methyl isonicotinate-κN)copper(II)

Elaheh Ahadi,a Hassan Hosseini-Monfareda* and Peter Mayerb

aDepartment of Chemistry, University of Zanjan 45195-313, Zanjan, Islamic Republic of Iran, and bLudwig-Maximilians-Universität, Department Chemie, Butenandtstrasse 5–13, 81377 München, Germany
*Correspondence e-mail: monfared@znu.ac.ir

Edited by A. M. Chippindale, University of Reading, England (Received 3 March 2015; accepted 12 April 2015; online 18 April 2015)

In the title compound, [CuCl2(C7H7NO2)2], the square-planar-coordinated CuII ion lies on a centre of symmetry and is bonded to two monodentate methyl­isonicotinate ligands through their N atoms and by two chloride ligands. The mol­ecules pack in a herringbone pattern. Perpendicular to [100] there are weak inter­molecular C—H⋯Cl and C—H⋯O contacts. Along [100] there are infinite chains of edge-sharing octa­hedra linked through the chlorido ligands

CCDC reference: 1059032

Similar articles

1. Related literature

For related structures, see: Vitorica-Yrezabal et al. (2011[Vitorica-Yrezabal, I. J., Sullivan, R. A., Purver, S. L., Curfs, C., Tang, C. C. & Brammer, L. (2011). CrystEngComm, 13, 3189-3196.]); Laing & Carr (1971[Laing, M. & Carr, G. (1971). J. Chem. Soc. A, pp. 1141-1144.]); Chen & Mak (2006[Chen, X.-D. & Mak, T. C. W. (2006). Inorg. Chim. Acta, 359, 685-689.]); Ge et al. (2006[Ge, C.-H., Kou, H.-Z., Ni, Z.-H., Jiang, Y.-B. & Cui, A.-L. (2006). Inorg. Chim. Acta, 359, 541-547.]); Chen et al. (2011[Chen, W.-T., Luo, Z.-G., Xu, Y.-P., Luo, Q.-Y. & Liu, J.-H. (2011). J. Chem. Res. (S), 35, 253-256.]); Ma et al. (2010[Ma, Z., Han, S., Kravtsov, V. C. & Moulton, B. (2010). Inorg. Chim. Acta, 363, 387-394.]). For background to isonicotinate, see: Zhou et al. (2006[Zhou, Y. Y., Yan, X. P., Kim, K. N., Wang, S. W. & Liu, M. G. (2006). J. Chromatogr. A, 1116, 172-178.]); Bera et al. (2001[Bera, J. K., Smucker, B. W., Walton, R. A. & Dunbar, K. R. (2001). Chem. Commun. pp. 2562-2563.]); Cotton et al. (2007[Cotton, F. A., Jin, J. Y., Li, Z., Liu, C. Y. & Murillo, C. A. (2007). Dalton Trans. pp. 2328-2335.]); Tella et al. (2014[Tella, A. C., Owalude, S. O., Ojekanmi, C. A. & Oluwafemi, O. S. (2014). New J. Chem. 38, 4494-4500.]). For the synthesis of 4-(5-phenyl-1,3,4-oxa­diazol-2-yl)pyridine, used in the preparation, see: Kangani & Day (2009[Kangani, C. O. & Day, B. W. (2009). Tetrahedron Lett. 50, 5332-5335.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • [CuCl2(C7H7NO2)2]

  • Mr = 408.71

  • Monoclinic, P 21 /n

  • a = 3.7792 (4) Å

  • b = 29.891 (4) Å

  • c = 7.0139 (8) Å

  • β = 94.036 (10)°

  • V = 790.36 (16) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.74 mm−1

  • T = 173 K

  • 0.50 × 0.05 × 0.04 mm

2.2. Data collection

  • Oxford Diffraction Xcalibur 3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2011[Oxford Diffraction (2011). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.775, Tmax = 1.000

  • 4265 measured reflections

  • 1617 independent reflections

  • 1404 reflections with I > 2σ(I)

  • Rint = 0.034

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.091

  • S = 1.09

  • 1617 reflections

  • 107 parameters

  • H-atom parameters constrained

  • Δρmax = 0.53 e Å−3

  • Δρmin = −0.69 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C2—H2⋯Cl1i 0.95 2.83 3.517 (3) 130
C7—H7B⋯O2ii 0.98 2.53 3.470 (4) 161
C7—H7C⋯O1iii 0.98 2.58 3.298 (4) 130
Symmetry codes: (i) x, y, z-1; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2011[Oxford Diffraction (2011). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.], 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

CCDC reference: 1059032

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S205698901500729X/cq2014sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901500729X/cq2014Isup2.hkl

checkCIF report


Comment top

Isonicotinate is a versatile ditopic ligand that has been used for various applications. The copper(II) isonicotinate (Cu(4–C5H4N-COO)2(H2O)4) coordination polymer has been explored as a sorbent in flow injection solid-phase extraction for determination of trace polycyclic aromatic hydrocarbons in environmental matrices [Zhou et al. (2006)]. The incorporation of both dinuclear (M2) and mononuclear (M') units into molecular squares has been achieved by reacting a triply bonded Re2(II,II) complex possessing two cis isonicotinate donor ligands with Pt(II) containing molecules with substitutionally labile cis trifluoromethanesulfonate groups [Bera et al. (2001)]. Quadruply bonded Mo24+ species having isonicotinate ligands bound through the carboxylate group have been designed to act as 'anglers' by luring metal-containing Lewis acids to bind to the N-pyridyl group [Cotton et al. (2007)]. The copper-isonicotinate metal-organic frameworks [Cu(INA)2] (INA = isonicotinate) (MOFs) have been prepared simply by mixing and heating solid reactants without milling. The adsorption of fluorescein dye on the as-synthesized [Cu(INA)2] has also been investigated [Tella et al. (2014)].

The molecular structure of the title compound possessing a crystallographic centre of inversion is depicted in Fig. 1. The first coordination sphere of the Cu1 centre consists of two nitrogen atoms, from the isoniconate ligands, at a distance of 2.025 (2) Å and two chlorido ligands at a distance of 2.2962 (7) Å. The various N1—Cu1—Cl1 angles are close to 90° resulting in a square-planar first coordination sphere of Cu1. By coordination of two additional chlorido ligands from adjacent complexes at a distance of 2.9215 (7) Å from the Cu1 centre, the coordination sphere is expanded to a distorted octahedron. The pyridine ring and the Cu1—Cl1 bond are not coplanar, but enclose an angle of 59.00 (9)°. The Cu—N1 bond and the plane of the pyridine ring deviate from coplanarity by an angle of 5.05 (11)°.

The herringbone pattern of the packing of the title compound is shown in Fig. 2. Perpendicular to [100] there are weak intermolecular C—H···Cl and C—H···O contacts with donor-acceptor distances of 3.517 (3) Å, 3.470 (4) Å and 3.298 (4) Å (C2···Cl1, C7···O2 and C7···O1, respectively). Along [100] there are infinite chains of edge-sharing octahedra linked through the chlorido ligands (Fig.3). This structural feature is found in many copper complexes consisting of two chlorido ligands and two pyridine derivatives, e.g. Vitorica-Yrezabel et al. (2011), Laing et al. (1971), Chen et al. (2006), Ge et al. (2006), Chen et al. (2011), Ma et al. (2010). Each bridging chlorido ligand has a short (2.2962 (7) Å) and a longer (2.9215 (7) Å) bond distance to the two adjacent Cu-centers. The bond angle at the bridging chloride ions is 92.03 (2)°. A consequence of the formation of the strands along [100] is π-stacking between adjacent pyridine rings. The average distance between the centres of gravity of adjacent rings is a = 3.7792 Å.

Related literature top

For related structures, see: Vitorica-Yrezabal et al. (2011); Laing & Carr (1971); Chen & Mak (2006); Ge et al. (2006); Chen et al. (2011); Ma et al. (2010). For background to isonicotinate, see: Zhou et al. (2006); Bera et al. (2001); Cotton et al. (2007); Tella et al. (2014). For the synthesis of 4-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridine, used in the preparation, see: Kangani & Day (2009).

Experimental top

The compound 4-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridine (0.04 g, 0.18 mmol, synthesised by a previously reported method [Kangani et al. (2009)], and copper(II) chloride dihydrate (0.015 g, 0.09 mmol) were placed in the main arm of a branched tube. Methanol (13 ml) was carefully added to fill the arms, the tube was sealed and the reagent-containing arm immersed in an oil bath at 60 °C while the other arm was kept at ambient temperature. After two weeks, green, needle shaped crystals were deposited in the cooler arm. The crystals were filtered, washed with methanol and air dried. Yield 19% (7.0 mg).

Refinement top

All hydrogen atoms were positioned geometrically and treated as riding on their parent atoms (aromatic C—H = 0.95 Å, methyl C—H = 0.98 Å, Uiso(H) = 1.2Ueq(C, aromatic), Uiso(H) = 1.5Ueq(C, methyl)). The methyl group was allowed to rotate along the C–O bond to best fit the experimental electron density.

Structure description top

Isonicotinate is a versatile ditopic ligand that has been used for various applications. The copper(II) isonicotinate (Cu(4–C5H4N-COO)2(H2O)4) coordination polymer has been explored as a sorbent in flow injection solid-phase extraction for determination of trace polycyclic aromatic hydrocarbons in environmental matrices [Zhou et al. (2006)]. The incorporation of both dinuclear (M2) and mononuclear (M') units into molecular squares has been achieved by reacting a triply bonded Re2(II,II) complex possessing two cis isonicotinate donor ligands with Pt(II) containing molecules with substitutionally labile cis trifluoromethanesulfonate groups [Bera et al. (2001)]. Quadruply bonded Mo24+ species having isonicotinate ligands bound through the carboxylate group have been designed to act as 'anglers' by luring metal-containing Lewis acids to bind to the N-pyridyl group [Cotton et al. (2007)]. The copper-isonicotinate metal-organic frameworks [Cu(INA)2] (INA = isonicotinate) (MOFs) have been prepared simply by mixing and heating solid reactants without milling. The adsorption of fluorescein dye on the as-synthesized [Cu(INA)2] has also been investigated [Tella et al. (2014)].

The molecular structure of the title compound possessing a crystallographic centre of inversion is depicted in Fig. 1. The first coordination sphere of the Cu1 centre consists of two nitrogen atoms, from the isoniconate ligands, at a distance of 2.025 (2) Å and two chlorido ligands at a distance of 2.2962 (7) Å. The various N1—Cu1—Cl1 angles are close to 90° resulting in a square-planar first coordination sphere of Cu1. By coordination of two additional chlorido ligands from adjacent complexes at a distance of 2.9215 (7) Å from the Cu1 centre, the coordination sphere is expanded to a distorted octahedron. The pyridine ring and the Cu1—Cl1 bond are not coplanar, but enclose an angle of 59.00 (9)°. The Cu—N1 bond and the plane of the pyridine ring deviate from coplanarity by an angle of 5.05 (11)°.

The herringbone pattern of the packing of the title compound is shown in Fig. 2. Perpendicular to [100] there are weak intermolecular C—H···Cl and C—H···O contacts with donor-acceptor distances of 3.517 (3) Å, 3.470 (4) Å and 3.298 (4) Å (C2···Cl1, C7···O2 and C7···O1, respectively). Along [100] there are infinite chains of edge-sharing octahedra linked through the chlorido ligands (Fig.3). This structural feature is found in many copper complexes consisting of two chlorido ligands and two pyridine derivatives, e.g. Vitorica-Yrezabel et al. (2011), Laing et al. (1971), Chen et al. (2006), Ge et al. (2006), Chen et al. (2011), Ma et al. (2010). Each bridging chlorido ligand has a short (2.2962 (7) Å) and a longer (2.9215 (7) Å) bond distance to the two adjacent Cu-centers. The bond angle at the bridging chloride ions is 92.03 (2)°. A consequence of the formation of the strands along [100] is π-stacking between adjacent pyridine rings. The average distance between the centres of gravity of adjacent rings is a = 3.7792 Å.

For related structures, see: Vitorica-Yrezabal et al. (2011); Laing & Carr (1971); Chen & Mak (2006); Ge et al. (2006); Chen et al. (2011); Ma et al. (2010). For background to isonicotinate, see: Zhou et al. (2006); Bera et al. (2001); Cotton et al. (2007); Tella et al. (2014). For the synthesis of 4-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridine, used in the preparation, see: Kangani & Day (2009).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2011); cell refinement: CrysAlis PRO (Oxford Diffraction, 2011); data reduction: CrysAlis PRO (Oxford Diffraction, 2011); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008, 2015); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound (ellipsoids drawn at the 30% probability level). Symmetry code: i = 1 - x, -y, 1 - z. Non-labelled non-hydrogen atoms have been generated by symmetry i.
[Figure 2] Fig. 2. The unit cell viewed along [100] (ellipsoids drawn at the 50% probability level). Intermolecular C—H···Cl and C—H···O contacts are indicated by dashed lines.
[Figure 3] Fig. 3. Infinite strands along [100] formed by intermolecular Cu—Cl bonds (thin bond diameter) (drawn at the 30% ellipsoid probability level).
Dichloridobis(methyl isonicotinate-κN)copper(II) top
Crystal data top
[CuCl2(C7H7NO2)2]F(000) = 414
Mr = 408.71Dx = 1.717 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 3.7792 (4) ÅCell parameters from 1293 reflections
b = 29.891 (4) Åθ = 4.5–26.3°
c = 7.0139 (8) ŵ = 1.74 mm−1
β = 94.036 (10)°T = 173 K
V = 790.36 (16) Å3Rod, green
Z = 20.50 × 0.05 × 0.04 mm
Data collection top
Oxford Diffraction Xcalibur 3
diffractometer		1617 independent reflections
Radiation source: fine-focus sealed tube1404 reflections with I > 2σ(I)
Detector resolution: 15.9809 pixels mm-1Rint = 0.034
ω scansθmax = 26.4°, θmin = 4.5°
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2011)		h = −4→4
Tmin = 0.775, Tmax = 1.000k = −33→37
4265 measured reflectionsl = −8→6
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.091 w = 1/[σ2(Fo2) + (0.0388P)2 + 0.6044P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
1617 reflectionsΔρmax = 0.53 e Å−3
107 parametersΔρmin = −0.69 e Å−3
Crystal data top
[CuCl2(C7H7NO2)2]V = 790.36 (16) Å3
Mr = 408.71Z = 2
Monoclinic, P21/nMo Kα radiation
a = 3.7792 (4) ŵ = 1.74 mm−1
b = 29.891 (4) ÅT = 173 K
c = 7.0139 (8) Å0.50 × 0.05 × 0.04 mm
β = 94.036 (10)°
Data collection top
Oxford Diffraction Xcalibur 3
diffractometer		1617 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2011)		1404 reflections with I > 2σ(I)
Tmin = 0.775, Tmax = 1.000Rint = 0.034
4265 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.091H-atom parameters constrained
S = 1.09Δρmax = 0.53 e Å−3
1617 reflectionsΔρmin = −0.69 e Å−3
107 parameters
Special details top

Experimental. Absorption correction: CrysAlisPro (Oxford Diffraction, 2011) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
xyzUiso*/Ueq
Cu10.50000.00000.50000.01825 (17)
Cl10.91406 (17)0.03090 (2)0.71647 (9)0.01768 (18)
O20.3701 (7)0.17679 (8)−0.1593 (3)0.0414 (7)
O10.1672 (6)0.20909 (6)0.0994 (3)0.0291 (5)
N10.4707 (6)0.05771 (7)0.3486 (3)0.0168 (5)
C10.5365 (7)0.05831 (9)0.1633 (4)0.0180 (6)
H10.61720.03160.10700.022*
C20.4918 (7)0.09617 (9)0.0505 (4)0.0197 (6)
H20.54440.0955−0.08000.024*
C30.3693 (7)0.13491 (9)0.1308 (4)0.0174 (6)
C40.3076 (8)0.13494 (9)0.3240 (4)0.0188 (6)
H40.22780.16130.38370.023*
C50.3647 (8)0.09584 (9)0.4276 (4)0.0202 (6)
H50.32720.09610.56010.024*
C60.3063 (8)0.17503 (10)0.0051 (4)0.0236 (7)
C70.0886 (11)0.24908 (11)−0.0132 (5)0.0384 (9)
H7A0.30900.2613−0.05770.058*
H7B−0.02240.27140.06570.058*
H7C−0.07390.2416−0.12360.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0235 (3)0.0123 (3)0.0184 (3)−0.00169 (19)−0.0021 (2)0.00175 (18)
Cl10.0186 (3)0.0170 (4)0.0175 (3)−0.0002 (3)0.0016 (3)−0.0023 (2)
O20.0712 (19)0.0277 (13)0.0274 (13)0.0115 (12)0.0191 (13)0.0092 (10)
O10.0465 (14)0.0169 (11)0.0239 (12)0.0100 (10)0.0035 (10)0.0022 (9)
N10.0175 (12)0.0144 (12)0.0185 (12)0.0009 (9)0.0002 (9)−0.0003 (9)
C10.0201 (14)0.0150 (14)0.0192 (14)0.0007 (11)0.0038 (11)−0.0031 (11)
C20.0220 (15)0.0190 (15)0.0185 (14)−0.0010 (11)0.0048 (11)−0.0006 (11)
C30.0169 (14)0.0141 (14)0.0210 (14)−0.0016 (10)0.0003 (11)0.0010 (11)
C40.0212 (14)0.0146 (14)0.0211 (15)0.0005 (11)0.0043 (11)−0.0029 (11)
C50.0242 (15)0.0186 (14)0.0184 (14)−0.0006 (12)0.0049 (12)−0.0007 (11)
C60.0254 (16)0.0192 (16)0.0264 (17)0.0002 (12)0.0023 (13)0.0000 (12)
C70.056 (2)0.0217 (17)0.037 (2)0.0133 (16)0.0034 (17)0.0075 (14)
Geometric parameters (Å, º) top
Cu1—N12.025 (2)C1—H10.9500
Cu1—N1i2.025 (2)C2—C31.382 (4)
Cu1—Cl12.2962 (7)C2—H20.9500
Cu1—Cl1i2.2962 (7)C3—C41.391 (4)
Cu1—Cl1ii2.9215 (7)C3—C61.498 (4)
Cu1—Cl1iii2.9215 (7)C4—C51.385 (4)
O2—C61.196 (4)C4—H40.9500
O1—C61.341 (3)C5—H50.9500
O1—C71.452 (4)C7—H7A0.9800
N1—C11.340 (4)C7—H7B0.9800
N1—C51.341 (3)C7—H7C0.9800
C1—C21.385 (4)
N1—Cu1—N1i180.00 (6)C3—C2—C1118.9 (3)
N1—Cu1—Cl190.79 (7)C3—C2—H2120.6
N1i—Cu1—Cl189.21 (7)C1—C2—H2120.6
N1—Cu1—Cl1i89.21 (7)C2—C3—C4118.8 (3)
N1i—Cu1—Cl1i90.79 (7)C2—C3—C6118.4 (3)
Cl1—Cu1—Cl1i180.0C4—C3—C6122.8 (3)
N1—Cu1—Cl1ii90.70 (7)C5—C4—C3118.7 (3)
N1i—Cu1—Cl1ii89.29 (7)C5—C4—H4120.7
Cl1—Cu1—Cl1ii87.97 (2)C3—C4—H4120.7
Cl1i—Cu1—Cl1ii92.03 (2)N1—C5—C4122.7 (3)
N1—Cu1—Cl1iii89.30 (7)N1—C5—H5118.6
N1i—Cu1—Cl1iii90.71 (7)C4—C5—H5118.6
Cl1—Cu1—Cl1iii92.03 (2)O2—C6—O1123.7 (3)
Cl1i—Cu1—Cl1iii87.97 (2)O2—C6—C3124.6 (3)
Cl1ii—Cu1—Cl1iii180.0O1—C6—C3111.7 (2)
C6—O1—C7115.4 (2)O1—C7—H7A109.5
C1—N1—C5118.1 (2)O1—C7—H7B109.5
C1—N1—Cu1120.86 (18)H7A—C7—H7B109.5
C5—N1—Cu1120.97 (19)O1—C7—H7C109.5
N1—C1—C2122.8 (3)H7A—C7—H7C109.5
N1—C1—H1118.6H7B—C7—H7C109.5
C2—C1—H1118.6
C5—N1—C1—C2−1.5 (4)Cu1—N1—C5—C4−173.5 (2)
Cu1—N1—C1—C2174.6 (2)C3—C4—C5—N1−1.3 (4)
N1—C1—C2—C3−1.0 (4)C7—O1—C6—O21.3 (5)
C1—C2—C3—C42.3 (4)C7—O1—C6—C3−178.5 (3)
C1—C2—C3—C6−177.2 (3)C2—C3—C6—O2−3.7 (5)
C2—C3—C4—C5−1.2 (4)C4—C3—C6—O2176.8 (3)
C6—C3—C4—C5178.3 (3)C2—C3—C6—O1176.1 (3)
C1—N1—C5—C42.7 (4)C4—C3—C6—O1−3.4 (4)
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+2, −y, −z+1; (iii) x−1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···Cl1iv0.952.833.517 (3)130
C7—H7B···O2v0.982.533.470 (4)161
C7—H7C···O1vi0.982.583.298 (4)130
Symmetry codes: (iv) x, y, z−1; (v) x−1/2, −y+1/2, z+1/2; (vi) x−1/2, −y+1/2, z−1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···Cl1i0.952.833.517 (3)130
C7—H7B···O2ii0.982.533.470 (4)161
C7—H7C···O1iii0.982.583.298 (4)130
Symmetry codes: (i) x, y, z−1; (ii) x−1/2, −y+1/2, z+1/2; (iii) x−1/2, −y+1/2, z−1/2.
 

Acknowledgements

The authors are grateful to the University of Zanjan and the School of Chemistry, Zanjan, and the Department of Chemistry of the LMU Munich for financial support.

References

First citationAltomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationBera, J. K., Smucker, B. W., Walton, R. A. & Dunbar, K. R. (2001). Chem. Commun. pp. 2562–2563.  Web of Science CSD CrossRef Google Scholar
 First citationBurnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.  Google Scholar
 First citationChen, W.-T., Luo, Z.-G., Xu, Y.-P., Luo, Q.-Y. & Liu, J.-H. (2011). J. Chem. Res. (S), 35, 253–256.  CSD CrossRef CAS Google Scholar
 First citationChen, X.-D. & Mak, T. C. W. (2006). Inorg. Chim. Acta, 359, 685–689.  CrossRef CAS Google Scholar
 First citationCotton, F. A., Jin, J. Y., Li, Z., Liu, C. Y. & Murillo, C. A. (2007). Dalton Trans. pp. 2328–2335.  Google Scholar
 First citationGe, C.-H., Kou, H.-Z., Ni, Z.-H., Jiang, Y.-B. & Cui, A.-L. (2006). Inorg. Chim. Acta, 359, 541–547.  CrossRef CAS Google Scholar
 First citationKangani, C. O. & Day, B. W. (2009). Tetrahedron Lett. 50, 5332–5335.  CrossRef CAS Google Scholar
 First citationLaing, M. & Carr, G. (1971). J. Chem. Soc. A, pp. 1141–1144.  CSD CrossRef Google Scholar
 First citationMa, Z., Han, S., Kravtsov, V. C. & Moulton, B. (2010). Inorg. Chim. Acta, 363, 387–394.  CSD CrossRef CAS Google Scholar
 First citationOxford Diffraction (2011). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationTella, A. C., Owalude, S. O., Ojekanmi, C. A. & Oluwafemi, O. S. (2014). New J. Chem. 38, 4494–4500.  CrossRef CAS Google Scholar
 First citationVitorica-Yrezabal, I. J., Sullivan, R. A., Purver, S. L., Curfs, C., Tang, C. C. & Brammer, L. (2011). CrystEngComm, 13, 3189–3196.  CAS Google Scholar
 First citationZhou, Y. Y., Yan, X. P., Kim, K. N., Wang, S. W. & Liu, M. G. (2006). J. Chromatogr. A, 1116, 172–178.  CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 5| May 2015| Pages m112-m113
https://doi.org/10.1107/S205698901500729X
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS