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In the title complex, [Cu(C8H7O2)2(C12H8N2)], the CuII atom is located on a twofold axis and assumes a distorted octahedral coordination geometry, formed by a phenanthroline mol­ecule and two methyl­benzoate anions, all in chelating mode. The carboxyl­ate group chelates to the CuII atom with greatly differing Cu—O distances, viz. 2.5923 (19) Å in the axial direction and 1.9435 (14) Å in the equatorial plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804025759/cv6393sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804025759/cv6393Isup2.hkl
Contains datablock I

CCDC reference: 255432

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.037
  • wR factor = 0.091
  • Data-to-parameter ratio = 16.7

checkCIF/PLATON results

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Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Cu - O2 .. 29.26 su
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C7 .. 5.15 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu - C7 .. 9.22 su PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for O2
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis(3-methylbenzoato-κ2O,O')(phenanthroline-κ2N,N')copper(II) top
Crystal data top
[Cu(C8H7O2)2(C12H8N2)]F(000) = 1060
Mr = 514.02Dx = 1.469 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 9404 reflections
a = 21.1482 (13) Åθ = 2.5–26.0°
b = 9.9476 (12) ŵ = 0.98 mm1
c = 11.9730 (8) ÅT = 295 K
β = 112.690 (2)°Platelet, blue
V = 2323.9 (4) Å30.31 × 0.27 × 0.08 mm
Z = 4
Data collection top
Rigaku R-AXIS Rapid
diffractometer
2666 independent reflections
Radiation source: fine-focus sealed tube2238 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
Detector resolution: 10.00 pixels mm-1θmax = 27.5°, θmin = 2.1°
ω scansh = 2727
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1212
Tmin = 0.740, Tmax = 0.920l = 1515
10454 measured reflections
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0446P)2 + 1.5001P]
where P = (Fo2 + 2Fc2)/3
2666 reflections(Δ/σ)max = 0.001
160 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.24 e Å3
Special details top

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.

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
Cu0.50000.51184 (3)0.25000.04226 (13)
N10.46902 (9)0.66473 (15)0.32655 (15)0.0431 (4)
O10.45542 (8)0.38096 (13)0.31579 (14)0.0526 (4)
O20.37805 (9)0.41747 (17)0.13177 (15)0.0656 (4)
C10.43676 (12)0.6610 (2)0.4019 (2)0.0522 (5)
H10.42770.57810.42840.063*
C20.41607 (13)0.7773 (2)0.4427 (2)0.0603 (6)
H20.39280.77120.49450.072*
C30.42973 (12)0.8992 (2)0.4072 (2)0.0552 (5)
H30.41580.97700.43440.066*
C40.46505 (11)0.90831 (19)0.32916 (18)0.0449 (5)
C50.48300 (10)0.78682 (17)0.29116 (17)0.0387 (4)
C60.48314 (12)1.03116 (19)0.2877 (2)0.0511 (5)
H60.47151.11250.31310.061*
C70.39637 (12)0.36362 (19)0.2318 (2)0.0482 (5)
C80.34897 (11)0.27118 (19)0.2618 (2)0.0462 (5)
C90.35649 (11)0.2508 (2)0.3809 (2)0.0503 (5)
H90.39130.29530.44260.060*
C100.31319 (12)0.1654 (2)0.4102 (2)0.0610 (6)
C110.26262 (13)0.0994 (3)0.3166 (3)0.0753 (8)
H110.23320.04120.33400.090*
C120.25477 (13)0.1179 (3)0.1985 (3)0.0798 (9)
H120.22040.07200.13720.096*
C130.29752 (13)0.2041 (3)0.1698 (2)0.0655 (6)
H130.29180.21680.08960.079*
C140.32262 (15)0.1445 (4)0.5406 (3)0.0894 (10)
H14A0.27910.12480.54460.134*
H14B0.34130.22460.58600.134*
H14C0.35340.07080.57390.134*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu0.0496 (2)0.02871 (17)0.0540 (2)0.0000.02611 (17)0.000
N10.0508 (10)0.0350 (8)0.0506 (10)0.0014 (7)0.0274 (8)0.0005 (7)
O10.0507 (9)0.0378 (7)0.0705 (10)0.0055 (6)0.0248 (8)0.0047 (7)
O20.0734 (11)0.0689 (11)0.0620 (10)0.0088 (9)0.0343 (9)0.0126 (9)
C10.0630 (14)0.0473 (11)0.0573 (13)0.0024 (10)0.0353 (11)0.0025 (10)
C20.0666 (15)0.0660 (14)0.0639 (15)0.0007 (11)0.0422 (13)0.0060 (12)
C30.0647 (14)0.0499 (11)0.0575 (13)0.0087 (10)0.0308 (11)0.0082 (10)
C40.0478 (11)0.0390 (10)0.0461 (11)0.0048 (8)0.0160 (9)0.0046 (8)
C50.0414 (10)0.0342 (9)0.0411 (10)0.0003 (7)0.0167 (8)0.0008 (8)
C60.0603 (14)0.0316 (9)0.0556 (13)0.0045 (8)0.0161 (10)0.0051 (9)
C70.0557 (13)0.0341 (9)0.0630 (13)0.0066 (8)0.0322 (11)0.0002 (9)
C80.0415 (11)0.0394 (9)0.0597 (13)0.0044 (8)0.0216 (10)0.0013 (9)
C90.0425 (11)0.0454 (10)0.0632 (13)0.0012 (9)0.0204 (10)0.0016 (10)
C100.0471 (13)0.0558 (12)0.0863 (17)0.0095 (10)0.0328 (12)0.0181 (12)
C110.0514 (15)0.0619 (14)0.123 (3)0.0092 (12)0.0449 (16)0.0024 (16)
C120.0488 (15)0.0806 (18)0.108 (2)0.0176 (13)0.0277 (15)0.0337 (18)
C130.0522 (14)0.0739 (16)0.0714 (16)0.0033 (12)0.0249 (12)0.0164 (13)
C140.0718 (19)0.109 (2)0.099 (2)0.0111 (17)0.0453 (17)0.0419 (19)
Geometric parameters (Å, º) top
Cu—O11.9435 (14)C6—H60.9300
Cu—O22.5923 (19)C7—C81.503 (3)
Cu—N12.0113 (16)C8—C131.385 (3)
N1—C11.325 (3)C8—C91.388 (3)
N1—C51.356 (2)C9—C101.389 (3)
O1—C71.278 (3)C9—H90.9300
O2—C71.230 (3)C10—C111.381 (4)
C1—C21.390 (3)C10—C141.510 (4)
C1—H10.9300C11—C121.371 (4)
C2—C31.353 (3)C11—H110.9300
C2—H20.9300C12—C131.382 (4)
C3—C41.407 (3)C12—H120.9300
C3—H30.9300C13—H130.9300
C4—C51.395 (2)C14—H14A0.9600
C4—C61.426 (3)C14—H14B0.9600
C5—C5i1.427 (4)C14—H14C0.9600
C6—C6i1.350 (5)
N1i—Cu—N181.75 (9)C6i—C6—H6119.5
O1—Cu—N191.59 (6)C4—C6—H6119.5
O1—Cu—N1i170.20 (6)O2—C7—O1123.6 (2)
O1i—Cu—O195.88 (9)O2—C7—C8120.7 (2)
O2—Cu—N195.30 (6)O1—C7—C8115.73 (19)
O2—Cu—N1i117.09 (6)C13—C8—C9119.3 (2)
O2—Cu—O156.13 (6)C13—C8—C7119.8 (2)
O2—Cu—O1i94.13 (6)C9—C8—C7120.8 (2)
O2—Cu—O2i137.53 (8)C8—C9—C10121.5 (2)
C1—N1—C5117.98 (17)C8—C9—H9119.2
C1—N1—Cu129.27 (14)C10—C9—H9119.2
C5—N1—Cu112.73 (12)C11—C10—C9117.7 (2)
C7—O1—Cu104.54 (13)C11—C10—C14121.7 (3)
N1—C1—C2122.04 (19)C9—C10—C14120.5 (3)
N1—C1—H1119.0C12—C11—C10121.4 (2)
C2—C1—H1119.0C12—C11—H11119.3
C3—C2—C1120.1 (2)C10—C11—H11119.3
C3—C2—H2119.9C11—C12—C13120.6 (3)
C1—C2—H2119.9C11—C12—H12119.7
C2—C3—C4119.91 (19)C13—C12—H12119.7
C2—C3—H3120.0C12—C13—C8119.4 (3)
C4—C3—H3120.0C12—C13—H13120.3
C5—C4—C3116.25 (18)C8—C13—H13120.3
C5—C4—C6119.08 (18)C10—C14—H14A109.5
C3—C4—C6124.68 (18)C10—C14—H14B109.5
N1—C5—C4123.69 (17)H14A—C14—H14B109.5
N1—C5—C5i116.40 (10)C10—C14—H14C109.5
C4—C5—C5i119.90 (11)H14A—C14—H14C109.5
C6i—C6—C4120.99 (12)H14B—C14—H14C109.5
Symmetry code: (i) x+1, y, z+1/2.
 

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