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Acta Cryst. (2007). E63, m1681    [ doi:10.1107/S1600536807024725 ]

Di-[mu]-chlorido-bis[(2-anilinobenzoato-[kappa]2O,O')(1,10-phenanthroline-[kappa]2N,N')copper(II)]

H. Jiang, J.-F. Ma and W.-L. Zhang

Abstract top

In the title compound, [Cu2(C13H10NO2)2Cl2(C12H8N2)2], the coordination geometry around the CuII atom is square-pyramidal, comprising one O atom from a 2-anilinobenzoate ligand, two N atoms from a 1,10-phenanthroline ligand and two Cl- anions. In addition, there is a weak interaction of 2.700 (2) Å between the CuII atom and the other O atom of the 2-anilinobenzoate ligand. The two Cl- anions bridge two CuII atoms to form a dimeric complex molecule, which lies on an inversion centre. There is an intramolecular N-H...O hydrogen bond in the 2-anilinobenzoate ligand.

Comment top

As part of our investigation of the transition metal complexes, there is a need to prepare further examples of these compounds. In this paper, the structure of the title compound, (I), is described.

As shown in Fig. 1, the coordination polyhedron around the CuII atom is a square pyramid, comprising one O atom from a 2-anilinobenzoate ligand, two N atoms from a 1,10-phenanthroline ligand and two Cl- anions. In addition, there is a weak interaction of 2.700 (2)Å between Cu1 and O2 (Table 1). The two Cl- anions bridge two CuII atoms to form a dimeric complex molecule, which lies on an inversion center. The bond distances and angles are normal (Atria et al., 1994). There exists intramolecular N—H···O hydrogen bond in (I) (Table 2).

Related literature top

For a related structure, see: Atria et al. (1994).

Experimental top

A mixture of CuCl2.2H2O (0.171 g, 1 mmol), NaOH (0.08 g, 2 mmol) and 2-anilinobenzoic acid (0.426 g, 2 mmol) in ethanol (15 ml) was stirred for 10 min at room temperature. Then 1,10-phenanthroline (0.360 g, 1 mmol) was added to the solution with stirring for 30 min and a blue precipitate was obtained. The precipitate was dissolved by dropwise addition of ammonia (5 M). Green single crystals were obtained by slow evaporation of the solution at room temperature.

Refinement top

H atoms on C atoms were poisitioned geometrically and refined as riding atoms, with C—H = 0.93 Å, and Uiso(H) = 1.2Ueq(C). H atom bonded to N atom was located in a difference Fourier map and refined with Uiso(H) = 1.5Ueq(N).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level. The dashed lines denote the weak interactions between Cu1 and O2. [Symmetry code: (i) -x + 1, -y + 1, -z + 1.]
Di-µ-chlorido-bis[(2-anilinobenzoato-κ2O,O')(1,10-phenanthroline- κ2N,N')copper(II)] top
Crystal data top
[Cu2(C13H10NO2)2Cl2(C12H8N2)2]F(000) = 1004
Mr = 982.83Dx = 1.511 Mg m−3
Monoclinic, P21/cMelting point: not measured K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 14.1685 (18) ÅCell parameters from 5099 reflections
b = 10.3545 (13) Åθ = 2.4–28.3°
c = 14.9955 (19) ŵ = 1.16 mm−1
β = 100.843 (2)°T = 293 K
V = 2160.7 (5) Å3Block, green
Z = 20.40 × 0.32 × 0.28 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		5099 independent reflections
Radiation source: fine-focus sealed tube3284 reflections with I > 2σ(I)
graphiteRint = 0.041
φ and ω scansθmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −18→17
Tmin = 0.643, Tmax = 0.718k = −6→13
12962 measured reflectionsl = −19→19
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0355P)2]
where P = (Fo2 + 2Fc2)/3
5099 reflections(Δ/σ)max = 0.001
292 parametersΔρmax = 0.30 e Å−3
0 restraintsΔρmin = −0.46 e Å−3
Crystal data top
[Cu2(C13H10NO2)2Cl2(C12H8N2)2]V = 2160.7 (5) Å3
Mr = 982.83Z = 2
Monoclinic, P21/cMo Kα radiation
a = 14.1685 (18) ŵ = 1.16 mm−1
b = 10.3545 (13) ÅT = 293 K
c = 14.9955 (19) Å0.40 × 0.32 × 0.28 mm
β = 100.843 (2)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		5099 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3284 reflections with I > 2σ(I)
Tmin = 0.643, Tmax = 0.718Rint = 0.041
12962 measured reflectionsθmax = 28.3°
Refinement top
R[F2 > 2σ(F2)] = 0.040H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092Δρmax = 0.30 e Å−3
S = 1.03Δρmin = −0.46 e Å−3
5099 reflectionsAbsolute structure: ?
292 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.38851 (2)0.57806 (3)0.46359 (2)0.03554 (11)
C10.2915 (2)0.7342 (3)0.2981 (2)0.0569 (8)
H10.28110.65670.26650.068*
C20.2601 (2)0.8483 (4)0.2536 (2)0.0775 (11)
H20.22980.84630.19290.093*
C30.2735 (2)0.9628 (4)0.2984 (3)0.0759 (10)
H30.25201.03910.26860.091*
C40.3194 (2)0.9658 (3)0.3892 (2)0.0517 (7)
C50.34946 (17)0.8467 (2)0.42921 (18)0.0380 (6)
C60.3382 (2)1.0797 (3)0.4440 (3)0.0643 (9)
H60.31881.15960.41860.077*
C70.3832 (2)1.0736 (3)0.5312 (3)0.0610 (9)
H70.39491.14950.56460.073*
C80.41356 (19)0.9538 (2)0.5737 (2)0.0463 (7)
C90.39598 (17)0.8408 (2)0.52190 (17)0.0361 (6)
C100.4697 (2)0.7138 (3)0.64042 (18)0.0504 (7)
H100.49050.63330.66350.060*
C110.4894 (2)0.8213 (3)0.6963 (2)0.0618 (9)
H110.52160.81190.75600.074*
C120.4614 (2)0.9394 (3)0.6635 (2)0.0592 (9)
H120.47411.01160.70080.071*
C130.2532 (2)0.4353 (2)0.36398 (18)0.0423 (6)
C140.20479 (18)0.3495 (2)0.28849 (16)0.0378 (6)
C150.2531 (2)0.3170 (2)0.21885 (17)0.0437 (7)
H150.31530.34740.22150.052*
C160.2121 (2)0.2417 (3)0.14645 (18)0.0502 (7)
H160.24630.22100.10120.060*
C170.1199 (2)0.1976 (3)0.14189 (19)0.0556 (8)
H170.09130.14680.09310.067*
C180.0694 (2)0.2279 (3)0.2089 (2)0.0560 (8)
H180.00680.19820.20420.067*
C190.1104 (2)0.3023 (2)0.28385 (19)0.0465 (7)
C20−0.00863 (19)0.2604 (3)0.38439 (19)0.0488 (7)
C21−0.0202 (2)0.1287 (3)0.3698 (2)0.0632 (9)
H210.01670.08570.33400.076*
C22−0.0867 (2)0.0609 (3)0.4082 (2)0.0725 (10)
H22−0.0947−0.02730.39750.087*
C23−0.1407 (2)0.1224 (4)0.4619 (2)0.0719 (10)
H23−0.18530.07610.48720.086*
C24−0.1289 (2)0.2532 (3)0.4784 (2)0.0618 (9)
H24−0.16430.29490.51610.074*
C25−0.0646 (2)0.3212 (3)0.43881 (19)0.0516 (7)
H25−0.05830.40980.44850.062*
N10.42259 (14)0.72155 (19)0.55568 (13)0.0364 (5)
N20.33596 (14)0.7321 (2)0.38417 (14)0.0389 (5)
O10.34218 (12)0.45837 (16)0.36536 (12)0.0441 (4)
O20.20849 (14)0.48232 (18)0.41969 (14)0.0598 (6)
Cl10.43055 (5)0.41708 (6)0.56938 (4)0.04377 (17)
N30.05935 (19)0.3350 (2)0.35103 (18)0.0620 (8)
H3N0.090 (2)0.397 (3)0.389 (2)0.093*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.04285 (19)0.02743 (17)0.03428 (18)−0.00175 (14)0.00194 (13)−0.00253 (13)
C10.0589 (19)0.058 (2)0.0487 (18)0.0005 (15)−0.0022 (15)0.0070 (15)
C20.081 (3)0.091 (3)0.051 (2)0.012 (2)−0.0102 (18)0.025 (2)
C30.076 (2)0.067 (2)0.081 (3)0.015 (2)0.006 (2)0.035 (2)
C40.0479 (17)0.0423 (17)0.068 (2)0.0088 (14)0.0174 (15)0.0180 (15)
C50.0344 (14)0.0360 (16)0.0454 (16)0.0014 (12)0.0123 (12)0.0065 (12)
C60.070 (2)0.0270 (16)0.102 (3)0.0102 (15)0.034 (2)0.0123 (17)
C70.067 (2)0.0284 (16)0.096 (3)−0.0064 (15)0.037 (2)−0.0112 (17)
C80.0443 (16)0.0332 (15)0.066 (2)−0.0051 (12)0.0230 (15)−0.0121 (14)
C90.0358 (14)0.0302 (14)0.0448 (15)−0.0009 (11)0.0135 (12)−0.0032 (11)
C100.0628 (19)0.0461 (17)0.0387 (16)0.0081 (14)0.0005 (14)−0.0069 (13)
C110.072 (2)0.068 (2)0.0414 (17)0.0049 (18)0.0004 (15)−0.0214 (16)
C120.061 (2)0.056 (2)0.061 (2)−0.0064 (16)0.0123 (16)−0.0331 (16)
C130.0507 (17)0.0294 (14)0.0457 (16)−0.0048 (13)0.0060 (13)−0.0034 (12)
C140.0416 (15)0.0302 (14)0.0390 (15)−0.0044 (11)0.0009 (12)−0.0004 (11)
C150.0470 (16)0.0391 (16)0.0428 (16)−0.0031 (13)0.0031 (13)0.0001 (13)
C160.063 (2)0.0471 (17)0.0391 (16)−0.0008 (15)0.0070 (14)−0.0035 (13)
C170.067 (2)0.0500 (18)0.0421 (17)−0.0128 (15)−0.0092 (15)−0.0066 (14)
C180.0500 (18)0.060 (2)0.0540 (19)−0.0205 (15)0.0002 (15)−0.0107 (15)
C190.0496 (17)0.0396 (16)0.0496 (17)−0.0097 (13)0.0078 (14)−0.0030 (13)
C200.0397 (16)0.0508 (18)0.0544 (18)−0.0098 (14)0.0056 (13)−0.0066 (14)
C210.064 (2)0.0524 (19)0.081 (2)−0.0103 (16)0.0342 (18)−0.0120 (17)
C220.079 (2)0.051 (2)0.091 (3)−0.0184 (18)0.026 (2)−0.0093 (18)
C230.058 (2)0.081 (3)0.084 (3)−0.0147 (19)0.0313 (19)0.001 (2)
C240.051 (2)0.072 (2)0.064 (2)0.0018 (17)0.0158 (16)−0.0056 (17)
C250.0470 (17)0.0515 (18)0.0541 (18)−0.0023 (14)0.0039 (14)−0.0076 (14)
N10.0443 (13)0.0316 (12)0.0330 (12)0.0019 (10)0.0060 (10)−0.0032 (9)
N20.0399 (12)0.0388 (13)0.0358 (12)−0.0010 (10)0.0016 (10)0.0026 (10)
O10.0398 (11)0.0433 (11)0.0462 (11)−0.0080 (8)0.0009 (8)−0.0105 (8)
O20.0577 (13)0.0571 (13)0.0682 (14)−0.0152 (10)0.0209 (11)−0.0282 (11)
Cl10.0519 (4)0.0330 (3)0.0466 (4)−0.0034 (3)0.0096 (3)0.0086 (3)
N30.0609 (17)0.0593 (18)0.0713 (19)−0.0270 (14)0.0264 (14)−0.0223 (14)
Geometric parameters (Å, °) top
Cu1—O11.9423 (16)C12—H120.9300
Cu1—N12.0241 (19)C13—O21.239 (3)
Cu1—N22.045 (2)C13—O11.279 (3)
Cu1—Cl12.3010 (7)C13—C141.500 (3)
Cu1—O22.700 (2)C14—C151.393 (3)
Cu1—Cl1i2.7011 (8)C14—C191.413 (3)
C1—N21.326 (3)C15—C161.373 (3)
C1—C21.388 (4)C15—H150.9300
C1—H10.9300C16—C171.374 (4)
C2—C31.359 (5)C16—H160.9300
C2—H20.9300C17—C181.374 (4)
C3—C41.395 (4)C17—H170.9300
C3—H30.9300C18—C191.396 (4)
C4—C51.402 (3)C18—H180.9300
C4—C61.433 (4)C19—N31.388 (3)
C5—N21.361 (3)C20—C211.386 (4)
C5—C91.423 (3)C20—C251.391 (4)
C6—C71.345 (4)C20—N31.399 (3)
C6—H60.9300C21—C221.384 (4)
C7—C81.424 (4)C21—H210.9300
C7—H70.9300C22—C231.367 (4)
C8—C121.396 (4)C22—H220.9300
C8—C91.400 (3)C23—C241.382 (4)
C9—N11.361 (3)C23—H230.9300
C10—N11.322 (3)C24—C251.372 (4)
C10—C111.389 (4)C24—H240.9300
C10—H100.9300C25—H250.9300
C11—C121.350 (4)Cl1—Cu1i2.7011 (8)
C11—H110.9300N3—H3N0.91 (3)
O1—Cu1—N1171.49 (8)O2—C13—O1122.9 (2)
O1—Cu1—N291.26 (8)O2—C13—C14121.5 (2)
O2—Cu1—N1121.94 (6)O1—C13—C14115.6 (2)
O2—Cu1—N285.45 (8)C15—C14—C19118.3 (2)
N1—Cu1—N280.73 (8)C15—C14—C13119.3 (2)
O1—Cu1—Cl193.86 (6)C19—C14—C13122.4 (2)
O2—Cu1—Cl190.70 (6)C16—C15—C14122.4 (3)
N1—Cu1—Cl193.65 (6)C16—C15—H15118.8
N2—Cu1—Cl1170.08 (6)C14—C15—H15118.8
O1—Cu1—Cl1i94.02 (6)C15—C16—C17119.0 (3)
O2—Cu1—Cl1i147.97 (6)C15—C16—H16120.5
N1—Cu1—Cl1i89.91 (6)C17—C16—H16120.5
N2—Cu1—Cl1i97.64 (6)C18—C17—C16120.5 (3)
Cl1—Cu1—Cl1i90.47 (2)C18—C17—H17119.7
O1—Cu1—O253.97 (7)C16—C17—H17119.7
N2—C1—C2122.2 (3)C17—C18—C19121.4 (3)
N2—C1—H1118.9C17—C18—H18119.3
C2—C1—H1118.9C19—C18—H18119.3
C3—C2—C1120.1 (3)N3—C19—C18121.7 (3)
C3—C2—H2119.9N3—C19—C14119.8 (2)
C1—C2—H2119.9C18—C19—C14118.5 (3)
C2—C3—C4119.9 (3)C21—C20—C25118.3 (3)
C2—C3—H3120.0C21—C20—N3123.8 (3)
C4—C3—H3120.0C25—C20—N3117.8 (3)
C3—C4—C5116.5 (3)C22—C21—C20120.2 (3)
C3—C4—C6125.4 (3)C22—C21—H21119.9
C5—C4—C6118.0 (3)C20—C21—H21119.9
N2—C5—C4123.5 (3)C23—C22—C21120.6 (3)
N2—C5—C9116.3 (2)C23—C22—H22119.7
C4—C5—C9120.2 (2)C21—C22—H22119.7
C7—C6—C4121.4 (3)C22—C23—C24120.0 (3)
C7—C6—H6119.3C22—C23—H23120.0
C4—C6—H6119.3C24—C23—H23120.0
C6—C7—C8121.6 (3)C25—C24—C23119.5 (3)
C6—C7—H7119.2C25—C24—H24120.2
C8—C7—H7119.2C23—C24—H24120.2
C12—C8—C9116.7 (3)C24—C25—C20121.3 (3)
C12—C8—C7125.1 (3)C24—C25—H25119.3
C9—C8—C7118.2 (3)C20—C25—H25119.3
N1—C9—C8122.9 (2)C10—N1—C9117.8 (2)
N1—C9—C5116.6 (2)C10—N1—Cu1128.62 (18)
C8—C9—C5120.5 (2)C9—N1—Cu1113.47 (16)
N1—C10—C11122.6 (3)C1—N2—C5117.7 (2)
N1—C10—H10118.7C1—N2—Cu1129.35 (19)
C11—C10—H10118.7C5—N2—Cu1112.90 (16)
C12—C11—C10119.6 (3)C13—O1—Cu1108.82 (16)
C12—C11—H11120.2Cu1—Cl1—Cu1i89.53 (2)
C10—C11—H11120.2C19—N3—C20127.8 (2)
C11—C12—C8120.3 (3)C19—N3—H3N112 (2)
C11—C12—H12119.9C20—N3—H3N116 (2)
C8—C12—H12119.9
Symmetry codes: (i) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O20.91 (3)1.88 (3)2.652 (3)142 (3)
Table 1
Selected geometric parameters (Å, °) top
Cu1—O11.9423 (16)Cu1—Cl12.3010 (7)
Cu1—N12.0241 (19)Cu1—O22.700 (2)
Cu1—N22.045 (2)Cu1—Cl1i2.7011 (8)
O1—Cu1—N1171.49 (8)N2—Cu1—Cl1170.08 (6)
O1—Cu1—N291.26 (8)O1—Cu1—Cl1i94.02 (6)
O2—Cu1—N1121.94 (6)O2—Cu1—Cl1i147.97 (6)
O2—Cu1—N285.45 (8)N1—Cu1—Cl1i89.91 (6)
N1—Cu1—N280.73 (8)N2—Cu1—Cl1i97.64 (6)
O1—Cu1—Cl193.86 (6)Cl1—Cu1—Cl1i90.47 (2)
O2—Cu1—Cl190.70 (6)O1—Cu1—O253.97 (7)
N1—Cu1—Cl193.65 (6)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O20.91 (3)1.88 (3)2.652 (3)142 (3)
Acknowledgements top

We thank the National Natural Science Foundation of China (No. 20471014), the Program for New Century Excellent Talents in Chinese Universities (NCET-05–0320), the Fok Ying Tung Education Foundation, and the Analysis and Testing Foundation of Northeast Normal University for support.

references
References top

Atria, A. M., Baggio, R. F., Garland, M. T. & Spodine, E. (1994). Acta Cryst. C50, 864–866.

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (1990). SHELXTL-Plus. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.