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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 5| May 2013| Page m277
https://doi.org/10.1107/S1600536813010350

Bis(cinnamato-κO)(1,10-phenanthroline-κ2N,N′)copper(II)

Meriem Benslimane,a* Yasmine Kheira Redjel,a Hocine Meraziga and Jean-Claude Daranb

aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université de Constantine 1, 25000 Constantine, Algeria, and bLaboratoire de Chimie de Coordination, UPR-CNRS 8241, 205 route de Narbonne, 31077 Toulouse Cedex 4, France
*Correspondence e-mail: b_meriem80@yahoo.fr

(Received 11 April 2013; accepted 16 April 2013; online 20 April 2013)

The title mononuclear CuII complex, [Cu(C9H7O2)2(C12H8N2)], is comprised of a CuII cation, two cinnamate (L−) ligands and a 1,10-phenanthroline (phen) ligand. The CuII atom and phen ligand lie on a twofold rotation axis. The CuII atom is coordinated by two O atoms from two carboxyl­ate groups of two (L−) ligands and two N atoms from one phen ligand, exhibiting a distorted square-planar geometry. In the crystal, mol­ecules are assembled into supra­molecular chains parallel to the c axis through weak C—H⋯O hydrogen bonds involving the phen and cinnamate ligands.

Related literature

1,10-Phenanthroline is of great inter­est in the field of supra­molecular chemistry as it can form C—H⋯O or C—H⋯N hydrogen bonds and π–π stacking inter­actions (Liu et al., 2004[Liu, C.-B., Sun, C.-Y., Jin, L.-P. & Lu, S.-Z. (2004). New J. Chem. 28, 1019-1026.]; Wang et al., 2003[Wang, Y., Zheng, X., Zhuang, W. & Jin, L. (2003). Eur. J. Inorg. Chem., pp. 3572-3582.]), which can effectively result in one-dimensional or two-dimensional networks.

[Scheme 1]

Experimental

Crystal data

  • [Cu(C9H7O2)2(C12H8N2)]

  • Mr = 538.04

  • Monoclinic, C 2/c

  • a = 24.486 (5) Å

  • b = 9.986 (5) Å

  • c = 10.710 (5) Å

  • β = 109.623 (5)°

  • V = 2466.7 (18) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.93 mm−1

  • T = 180 K

  • 0.35 × 0.17 × 0.09 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008a[Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.]) Tmin = 0.797, Tmax = 1.000

  • 6897 measured reflections

  • 2172 independent reflections

  • 1698 reflections with I > 2σ(I)

  • Rint = 0.050
Refinement

  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.100

  • S = 1.08

  • 2172 reflections

  • 168 parameters

  • H-atom parameters constrained

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.37 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C14—H14⋯O2i 0.93 2.49 3.176 (5) 131
Symmetry code: (i) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2012[Bruker (2012). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2012[Bruker (2012). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]) and ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813010350/vm2193sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813010350/vm2193Isup2.hkl

checkCIF report


Comment top

The mononuclear metal complexes of the chelating bidentate 1,10-phenanthroline (phen) and 2,2'-bipyridine (bipy) ligands are well known in the literature, and have been used in many fields. In the realm of coordination polymers, these complexes have been employed as coordination acceptor nodes for the construction of low dimensional polymer-based magnets exhibiting long-range magnetic ordering and spin crossover transitions. 1,10-Phenanthroline is of great interest in the field of supramolecular chemistry, because it can bring C—H···O or C—H···N hydrogen bonds and π-π stacking interactions (Liu et al., 2004 and Wang et al., 2003), which can effectively result in one-dimensional or two-dimensional networks. We report here the preparation and crystal structure of the title compound,[Cu(C9H7O2)2(C12H8N2)].

The asymmetric unit contains a half CuII cation, a half phen ligand and one cinnamic ligand (L-: C6H5—CH=CH-COO-). The CuII atom lies on a twofold rotation axis. In the complex, two equivalent L- anions function as monodentate ligands, while one phen molecule functions as a terminal ligand adopting the expected chelating mode to coordinate with one CuII ion, forming a mononuclear unit. The CuII ion is coordinated by two O atoms (O1, O1i, symmetry code (i): -x, y, -z + 1/2) from two cinnamic ligands, two N atoms (N1,N1i) from 1,10-phenanthroline molecules, exhibiting essentially distorted square planar geometry (Fig. 1). The Cu–N/O bonds distances are 2.018 (3) Å and 1.948 (3) Å, respectively. The carboxylate group shows a distortion from the molecular plane; the dihedral angle between the mean-plane (C3—C9) and the carboxlate group (O1/C1/O2) is 25.8 (4)°. The two carboxylate groups are almost perpendicular to one another with a dihedral angle of 78.9 (6)°.

In the crystal, molecules are assembled into one dimensional supramolecular chains parallel to the c axis through weak C—H···O hydrogen bonds involving the phen and carboxylate ligands (Table 1, Fig. 2).

Related literature top

1,10-Phenanthroline is of great interest in the field of supramolecular chemistry as it can form C—H···O or C—H···N hydrogen bonds and π–π stacking interactions (Liu et al., 2004; Wang et al., 2003), which can effectively result in one-dimensional or two-dimensional networks.

Experimental top

A methanol solution (5 ml) of phen (0.046 mg, 0.25 mmol) and cinnamic acid (0.07 mg, 0.5 mmol) were added dropwise to a methanol solution of (5 ml) CuSO4.5H2O (0.058 mg, 0.25 mmol) with constant stirring during 1 h. The mixture was then filtered and the filtrate allowed to stand for 10 days, after which small blue block-like crystals of the title complex were obtained.

Refinement top

The C-bound hydrogen atoms were placed in geometrically idealized positions and constrained to ride on their parent atom positions with a C–H distances of 0.93 Å and with Uiso(H) = 1.2Ueq(C).

Structure description top

The mononuclear metal complexes of the chelating bidentate 1,10-phenanthroline (phen) and 2,2'-bipyridine (bipy) ligands are well known in the literature, and have been used in many fields. In the realm of coordination polymers, these complexes have been employed as coordination acceptor nodes for the construction of low dimensional polymer-based magnets exhibiting long-range magnetic ordering and spin crossover transitions. 1,10-Phenanthroline is of great interest in the field of supramolecular chemistry, because it can bring C—H···O or C—H···N hydrogen bonds and π-π stacking interactions (Liu et al., 2004 and Wang et al., 2003), which can effectively result in one-dimensional or two-dimensional networks. We report here the preparation and crystal structure of the title compound,[Cu(C9H7O2)2(C12H8N2)].

The asymmetric unit contains a half CuII cation, a half phen ligand and one cinnamic ligand (L-: C6H5—CH=CH-COO-). The CuII atom lies on a twofold rotation axis. In the complex, two equivalent L- anions function as monodentate ligands, while one phen molecule functions as a terminal ligand adopting the expected chelating mode to coordinate with one CuII ion, forming a mononuclear unit. The CuII ion is coordinated by two O atoms (O1, O1i, symmetry code (i): -x, y, -z + 1/2) from two cinnamic ligands, two N atoms (N1,N1i) from 1,10-phenanthroline molecules, exhibiting essentially distorted square planar geometry (Fig. 1). The Cu–N/O bonds distances are 2.018 (3) Å and 1.948 (3) Å, respectively. The carboxylate group shows a distortion from the molecular plane; the dihedral angle between the mean-plane (C3—C9) and the carboxlate group (O1/C1/O2) is 25.8 (4)°. The two carboxylate groups are almost perpendicular to one another with a dihedral angle of 78.9 (6)°.

In the crystal, molecules are assembled into one dimensional supramolecular chains parallel to the c axis through weak C—H···O hydrogen bonds involving the phen and carboxylate ligands (Table 1, Fig. 2).

1,10-Phenanthroline is of great interest in the field of supramolecular chemistry as it can form C—H···O or C—H···N hydrogen bonds and π–π stacking interactions (Liu et al., 2004; Wang et al., 2003), which can effectively result in one-dimensional or two-dimensional networks.

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008b).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii [symmetry code: (i): -x, y, -z + 1/2].
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed down the a axis. Hydrogen bonds are shown as dashed lines.
Bis(cinnamato-κO)(1,10-phenanthroline-κ2N,N')copper(II) top
Crystal data top
[Cu(C9H7O2)2(C12H8N2)]F(000) = 1108
Mr = 538.04Dx = 1.449 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1791 reflections
a = 24.486 (5) Åθ = 2.8–24.9°
b = 9.986 (5) ŵ = 0.93 mm−1
c = 10.710 (5) ÅT = 180 K
β = 109.623 (5)°Platelet, blue
V = 2466.7 (18) Å30.35 × 0.17 × 0.09 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer		2172 independent reflections
Radiation source: fine-focus sealed tube1698 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
φ and ω scansθmax = 25.1°, θmin = 3.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008a)		h = −29→28
Tmin = 0.797, Tmax = 1.000k = −11→11
6897 measured reflectionsl = −12→12
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0509P)2]
where P = (Fo2 + 2Fc2)/3
2172 reflections(Δ/σ)max < 0.001
168 parametersΔρmax = 0.37 e Å−3
0 restraintsΔρmin = −0.37 e Å−3
Crystal data top
[Cu(C9H7O2)2(C12H8N2)]V = 2466.7 (18) Å3
Mr = 538.04Z = 4
Monoclinic, C2/cMo Kα radiation
a = 24.486 (5) ŵ = 0.93 mm−1
b = 9.986 (5) ÅT = 180 K
c = 10.710 (5) Å0.35 × 0.17 × 0.09 mm
β = 109.623 (5)°
Data collection top
Bruker APEXII CCD
diffractometer		2172 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008a)		1698 reflections with I > 2σ(I)
Tmin = 0.797, Tmax = 1.000Rint = 0.050
6897 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.100H-atom parameters constrained
S = 1.08Δρmax = 0.37 e Å−3
2172 reflectionsΔρmin = −0.37 e Å−3
168 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
xyzUiso*/Ueq
Cu10.00000.45859 (4)0.25000.03280 (19)
O10.04096 (9)0.59098 (18)0.3818 (2)0.0401 (5)
O20.10280 (9)0.5414 (2)0.2789 (2)0.0519 (6)
N1−0.03295 (11)0.3059 (2)0.1237 (2)0.0347 (6)
C10.09029 (13)0.6012 (3)0.3663 (3)0.0370 (7)
C40.17627 (13)0.7909 (3)0.6862 (3)0.0395 (7)
C30.13359 (13)0.7143 (3)0.5815 (3)0.0408 (7)
H30.10230.68080.60230.049*
C10−0.01823 (13)0.1841 (2)0.1824 (3)0.0356 (7)
C20.13404 (13)0.6868 (3)0.4616 (3)0.0404 (7)
H20.16350.72320.43550.049*
C11−0.03787 (14)0.0630 (3)0.1159 (3)0.0441 (8)
C15−0.01798 (15)−0.0590 (3)0.1870 (4)0.0557 (10)
H15−0.0303−0.14040.14460.067*
C13−0.08989 (16)0.1950 (3)−0.0730 (3)0.0532 (9)
H13−0.11480.2016−0.16010.064*
C14−0.06717 (14)0.3102 (3)−0.0004 (3)0.0452 (8)
H14−0.07660.3932−0.04150.054*
C12−0.07512 (16)0.0728 (3)−0.0149 (4)0.0553 (9)
H12−0.0900−0.0045−0.06270.066*
C50.22409 (15)0.8532 (3)0.6695 (4)0.0561 (9)
H50.22990.84610.58820.067*
C90.16966 (16)0.8046 (4)0.8080 (4)0.0679 (11)
H90.13810.76430.82270.081*
C60.26283 (16)0.9246 (4)0.7689 (4)0.0698 (11)
H60.29460.96490.75530.084*
C70.25464 (18)0.9363 (4)0.8886 (4)0.0843 (14)
H70.28070.98540.95660.101*
C80.20818 (19)0.8758 (5)0.9079 (4)0.0931 (16)
H80.20270.88310.98950.112*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0344 (3)0.0269 (3)0.0355 (3)0.0000.0096 (2)0.000
O10.0352 (12)0.0329 (10)0.0490 (13)−0.0009 (9)0.0099 (10)−0.0058 (9)
O20.0536 (14)0.0582 (13)0.0475 (14)−0.0047 (11)0.0216 (12)−0.0047 (11)
N10.0404 (15)0.0285 (12)0.0361 (15)−0.0019 (10)0.0141 (12)−0.0016 (10)
C10.0395 (18)0.0278 (14)0.0384 (18)0.0010 (13)0.0061 (14)0.0090 (13)
C40.0333 (17)0.0362 (15)0.045 (2)−0.0030 (13)0.0084 (15)−0.0023 (13)
C30.0328 (17)0.0355 (16)0.051 (2)−0.0023 (13)0.0105 (15)0.0022 (14)
C100.0384 (18)0.0282 (14)0.0481 (18)−0.0020 (12)0.0249 (15)−0.0033 (12)
C20.0355 (17)0.0387 (16)0.044 (2)−0.0061 (13)0.0098 (15)0.0046 (13)
C110.0487 (19)0.0355 (16)0.056 (2)−0.0084 (14)0.0275 (17)−0.0119 (14)
C150.067 (3)0.0255 (15)0.087 (3)−0.0056 (15)0.043 (2)−0.0087 (14)
C130.060 (2)0.056 (2)0.040 (2)−0.0139 (17)0.0126 (18)−0.0140 (16)
C140.052 (2)0.0440 (17)0.039 (2)−0.0028 (15)0.0138 (17)−0.0022 (14)
C120.064 (2)0.0479 (19)0.061 (2)−0.0189 (17)0.030 (2)−0.0251 (16)
C50.054 (2)0.062 (2)0.055 (2)−0.0205 (18)0.0213 (18)−0.0090 (17)
C90.054 (2)0.095 (3)0.061 (3)−0.031 (2)0.028 (2)−0.027 (2)
C60.056 (2)0.075 (2)0.080 (3)−0.0317 (19)0.025 (2)−0.019 (2)
C70.066 (3)0.108 (3)0.078 (3)−0.044 (3)0.024 (2)−0.047 (3)
C80.080 (3)0.142 (4)0.067 (3)−0.052 (3)0.039 (3)−0.049 (3)
Geometric parameters (Å, º) top
Cu1—O11.948 (2)C11—C151.433 (4)
Cu1—O1i1.948 (2)C15—C15i1.342 (7)
Cu1—N12.018 (2)C15—H150.9300
Cu1—N1i2.018 (2)C13—C121.363 (5)
O1—C11.277 (3)C13—C141.395 (4)
O2—C11.232 (3)C13—H130.9300
N1—C141.313 (4)C14—H140.9300
N1—C101.360 (3)C12—H120.9300
C1—C21.479 (4)C5—C61.365 (5)
C4—C91.374 (5)C5—H50.9300
C4—C51.390 (4)C9—C81.365 (5)
C4—C31.466 (4)C9—H90.9300
C3—C21.316 (4)C6—C71.368 (5)
C3—H30.9300C6—H60.9300
C10—C111.404 (4)C7—C81.364 (5)
C10—C10i1.424 (6)C7—H70.9300
C2—H20.9300C8—H80.9300
C11—C121.395 (5)
N1—Cu1—N1i81.84 (14)C11—C15—H15119.1
C1—O1—Cu1103.84 (18)C12—C13—C14119.3 (3)
C14—N1—C10118.5 (2)C12—C13—H13120.4
C14—N1—Cu1129.00 (19)C14—C13—H13120.4
C10—N1—Cu1112.4 (2)N1—C14—C13122.4 (3)
O2—C1—O1123.2 (3)N1—C14—H14118.8
O2—C1—C2119.8 (3)C13—C14—H14118.8
O1—C1—C2117.0 (3)C13—C12—C11120.3 (3)
C9—C4—C5116.8 (3)C13—C12—H12119.8
C9—C4—C3119.8 (3)C11—C12—H12119.8
C5—C4—C3123.4 (3)C6—C5—C4121.9 (3)
C2—C3—C4128.1 (3)C6—C5—H5119.1
C2—C3—H3115.9C4—C5—H5119.1
C4—C3—H3115.9C8—C9—C4121.7 (3)
N1—C10—C11122.9 (3)C8—C9—H9119.1
N1—C10—C10i116.64 (16)C4—C9—H9119.1
C11—C10—C10i120.45 (19)C5—C6—C7119.6 (3)
C3—C2—C1123.5 (3)C5—C6—H6120.2
C3—C2—H2118.2C7—C6—H6120.2
C1—C2—H2118.2C8—C7—C6119.8 (4)
C12—C11—C10116.5 (3)C8—C7—H7120.1
C12—C11—C15125.7 (3)C6—C7—H7120.1
C10—C11—C15117.8 (3)C9—C8—C7120.3 (4)
C15i—C15—C11121.72 (19)C9—C8—H8119.9
C15i—C15—H15119.1C7—C8—H8119.9
Symmetry code: (i) −x, y, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O2ii0.932.493.176 (5)131
Symmetry code: (ii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula[Cu(C9H7O2)2(C12H8N2)]
Mr538.04
Crystal system, space groupMonoclinic, C2/c
Temperature (K)180
a, b, c (Å)24.486 (5), 9.986 (5), 10.710 (5)
β (°) 109.623 (5)
V (Å3)2466.7 (18)
Z4
Radiation typeMo Kα
µ (mm−1)0.93
Crystal size (mm)0.35 × 0.17 × 0.09
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2008a)
Tmin, Tmax0.797, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		6897, 2172, 1698
Rint0.050
(sin θ/λ)max (Å−1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.100, 1.08
No. of reflections2172
No. of parameters168
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.37, −0.37

Computer programs: APEX2 (Bruker, 2012), SAINT (Bruker, 2012), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008b), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O2i0.93002.49003.176 (5)131.00
Symmetry code: (i) −x, −y+1, −z.
 

Acknowledgements

This work was supported by the University of Mentouri-Constantine, Algeria.

References

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 5| May 2013| Page m277
https://doi.org/10.1107/S1600536813010350
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