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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): m1526–m1527.
Published online 2008 November 13. doi:  10.1107/S1600536808036283
PMCID: PMC2959880

(2,9-Dimethyl-1,10-phenanthroline-κ2 N,N′)bis­(2-hydroxy­benzoato-κO)copper(II)

Abstract

The CuII atoms in the two independent mol­ecules of the title compound, [Cu(C7H5O3)2(C14H12N2)], are each coordinated by a bidentate 2,9-dimethyl-1,10-phenanthroline (dmphen) mol­ecule and two monodentate 2-hydroxy­benzoate anions in a distorted tetra­hedral geometry. The crystal packing is stabilized by intra­molecular hydrogen bonding and π–π inter­actions between the dmphen rings of neighboring mol­ecules, with distances between their ring planes of 3.5670 (4) and 3.5181 (9) Å.

Related literature

For the features of metal–phenanthroline complexes, see: Naing et al. (1995 [triangle]); Wang et al. (1996 [triangle]); Wall et al. (1999 [triangle]). For related structures, see: Cheng et al. (2007 [triangle]); Xuan et al. (2007 [triangle]); Zhao et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1526-scheme1.jpg

Experimental

Crystal data

  • [Cu(C7H5O3)2(C14H12N2)]
  • M r = 546.02
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1526-efi9.jpg
  • a = 23.819 (2) Å
  • b = 12.2576 (11) Å
  • c = 17.9084 (17) Å
  • β = 112.023 (1)°
  • V = 4847.0 (8) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.95 mm−1
  • T = 291 (2) K
  • 0.30 × 0.21 × 0.19 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004 [triangle]) T min = 0.765, T max = 0.837
  • 30637 measured reflections
  • 8932 independent reflections
  • 5274 reflections with I > 2σ(I)
  • R int = 0.060

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.121
  • S = 1.01
  • 8932 reflections
  • 675 parameters
  • H-atom parameters constrained
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: APEX2 and SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808036283/hg2438sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036283/hg2438Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

Financial support from the Science Fund of Henan Province for Distinguished Young Scholars (No. 074100510005) is gratefully acknowledged.

supplementary crystallographic information

Comment

Metal-phenanthroline complexes have attracted much attention because of their peculiar features (Wang et al., 1996; Wall et al., 1999; Naing et al., 1995). Some Cu(II)-phenanthroline complexes have been synthesized and structures were determined (Cheng et al., 2007; Xuan et al., 2007; Zhao et al., 2007). Recently, we obtained the title compound copper(II) complex (I), by reaction of 2,9-dimethyl-1,10-phenanthroline, 2-hydroxybenzoic acid and Cu(NO3)2 in an ethanol/water mixture. The structure of the title compound, Cu(C14H12N2)(C6H4OHCOO)2,(I), is shown below.

There are two independent molecules in the asymmetric unit. Each CuII ion is four-coordinated by two N atoms from a 2,9-dimethyl-1,10-phenanthroline ligand, and two O atoms from two 2-hydroxybenzoic anions. The CuII ion locates in the center, and CuO2N2 unit forms a distorted tetrahedral geometry (Fig.1). The Cu—N and Cu—O bond lengths in two independent molecules different slightly (Table 1). The hydroxy directions of 2-hydroxybenzoic anions in the two independent molecules are also different.

An intramolecular hydrogen bond between the hydroxy group and uncoordinated carboxyl O atom stabilizes the conformation of the hydroxybenzoate ligands (Table 2). A partially overlapped arrangement of neighboring parallel Cu1A-dmphen [symmetry code: (Cu1A) x, y - 1, z] and Cu1B-dmphen rings [symmetry code: (Cu1B) -x + 1, -y + 1, -z + 1], Cu2A-dmphen [symmetry code: (Cu2A) -x + 2, y - 1/2, -z + 3/2] and Cu2C-dmphen rings [symmetry code: (Cu2C) x, -y - 1/2, z + 3/2] are observed in the structure of (I) (Fig.2). The shorter face-to-face separation of 3.5670 (4)Å and 3.5181 (9)Å indicates the existence of π—π stacking between the dmphen ligands.

Experimental

2-hydroxybenzoic acid (0.1389 g, 1 mmol) and NaOH (0.0370 g, 1 mmol) were dissolved in distilled water(10 ml) and Cu(NO3)2.3H2O (0.1222 g, 0.5 mmol) were added. This solution was added to a solution of 2,9-dimethyl-1,10-phenanthroline hemihydrate (C14H12N2.0.5H2O, 0.1090 g, 0.5 mmol) in ethanol (10 ml). The mixture was stirred at 323 K and then refluxed for 5 h, cooled to room temperature and filtered. Green single crystals of (I) were appeared over a period of eighteen days by slow evaporation at room temperature.

Refinement

Methyl H and hydroxy H atoms were placed in calculated positions,with C—H=0.96 and O—H=0.82 Å, and refined with free torsion angles to fit the electron density; Uiso(H) = 1.5Ueq(carrier). Other H atoms were placed in calculated positions, with C—H=0.93 Å, and refined in the riding-model approximation with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of the title complex(I), with atom labels and 30% probability displacement ellipsoids.
Fig. 2.
π—π interactions of neighboring molecules and intramolecular hydrogen bonds in the crystal structure of (I).[symmetry code: (Cu1A) x, y - 1, z; (Cu1B) -x + 1, -y + 1, -z + 1; (Cu1D) -x + 1, -y + 2, -z + 1; (Cu2A) -x + 2, y - 1/2, ...

Crystal data

[Cu(C7H5O3)2(C14H12N2)]F000 = 2248
Mr = 546.02Dx = 1.496 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3270 reflections
a = 23.819 (2) Åθ = 2.4–19.2º
b = 12.2576 (11) ŵ = 0.95 mm1
c = 17.9084 (17) ÅT = 291 (2) K
β = 112.023 (1)ºBlock, green
V = 4847.0 (8) Å30.30 × 0.21 × 0.19 mm
Z = 8

Data collection

Bruker APEXII CCD area-detector diffractometer8932 independent reflections
Radiation source: fine-focus sealed tube5274 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.060
T = 291(2) Kθmax = 25.5º
[var phi] and ω scansθmin = 2.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)h = −28→27
Tmin = 0.765, Tmax = 0.837k = −14→14
30637 measured reflectionsl = −21→21

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.122  w = 1/[σ2(Fo2) + (0.051P)2 + 0.2481P] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
8932 reflectionsΔρmax = 0.38 e Å3
675 parametersΔρmin = −0.45 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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)

xyzUiso*/Ueq
Cu10.416752 (19)0.76816 (4)0.34347 (3)0.04372 (14)
Cu20.91833 (2)0.24372 (4)0.06488 (3)0.04679 (15)
O10.42604 (14)0.5478 (3)0.36158 (18)0.0828 (10)
O20.37117 (12)0.6601 (2)0.26599 (15)0.0537 (7)
O30.4003 (2)0.3447 (3)0.3513 (2)0.1039 (13)
H30.41770.40140.37140.156*
O40.42450 (12)0.8580 (2)0.25824 (15)0.0525 (7)
O50.33691 (13)0.9202 (2)0.25654 (16)0.0636 (8)
O60.26673 (13)1.0250 (3)0.13213 (18)0.0715 (8)
H60.27740.99780.17720.107*
O70.92602 (13)0.4499 (2)0.07908 (17)0.0690 (8)
O80.85069 (12)0.3372 (2)0.06067 (17)0.0611 (7)
O90.90651 (19)0.6548 (3)0.0833 (3)0.1015 (12)
H90.92640.59950.08530.152*
O100.92554 (11)0.1888 (2)0.16999 (15)0.0540 (7)
O110.84406 (12)0.0976 (2)0.09313 (15)0.0568 (7)
O120.79075 (13)−0.0325 (2)0.15603 (18)0.0675 (8)
H120.7973−0.00090.11980.101*
N10.38290 (13)0.7629 (2)0.43145 (16)0.0390 (7)
N20.49111 (13)0.8211 (2)0.43227 (17)0.0404 (7)
N30.90189 (14)0.1985 (2)−0.05127 (18)0.0461 (8)
N41.00369 (13)0.2094 (2)0.08003 (19)0.0456 (8)
C10.35133 (17)0.4709 (3)0.2453 (2)0.0479 (10)
C20.3600 (2)0.3653 (4)0.2763 (3)0.0668 (12)
C30.3263 (3)0.2798 (4)0.2294 (4)0.0814 (16)
H3A0.33050.20980.25090.098*
C40.2874 (2)0.2979 (4)0.1529 (4)0.0787 (15)
H40.26600.23970.12200.094*
C50.27904 (19)0.4010 (4)0.1202 (3)0.0681 (12)
H50.25240.41250.06750.082*
C60.31061 (17)0.4865 (3)0.1665 (2)0.0543 (10)
H6A0.30470.55640.14480.065*
C70.38553 (18)0.5648 (4)0.2941 (2)0.0521 (10)
C80.36927 (17)0.9750 (3)0.1521 (2)0.0444 (9)
C90.3138 (2)1.0240 (3)0.1071 (2)0.0552 (11)
C100.3058 (2)1.0737 (4)0.0339 (3)0.0713 (13)
H100.26881.10550.00370.086*
C110.3519 (3)1.0761 (4)0.0061 (3)0.0842 (16)
H110.34591.1088−0.04310.101*
C120.4071 (2)1.0306 (4)0.0503 (3)0.0806 (14)
H12A0.43861.03370.03170.097*
C130.4154 (2)0.9797 (3)0.1232 (2)0.0606 (11)
H130.45270.94830.15290.073*
C140.37703 (19)0.9146 (3)0.2272 (2)0.0474 (10)
C150.32818 (16)0.7343 (3)0.4286 (2)0.0445 (9)
C160.31365 (18)0.7396 (3)0.4971 (2)0.0535 (10)
H160.27530.71830.49380.064*
C170.35443 (19)0.7751 (3)0.5680 (3)0.0545 (11)
H170.34460.77700.61360.065*
C180.41203 (17)0.8093 (3)0.5725 (2)0.0452 (9)
C190.45829 (19)0.8514 (3)0.6437 (2)0.0568 (11)
H190.45100.85550.69120.068*
C200.5121 (2)0.8852 (3)0.6438 (2)0.0603 (11)
H200.54080.91400.69050.072*
C210.52535 (16)0.8772 (3)0.5721 (2)0.0467 (10)
C220.58051 (18)0.9085 (3)0.5682 (2)0.0587 (11)
H220.61040.94030.61250.070*
C230.59019 (17)0.8921 (3)0.4987 (2)0.0579 (11)
H230.62720.91180.49620.069*
C240.54513 (16)0.8458 (3)0.4307 (2)0.0479 (10)
C250.48185 (16)0.8339 (3)0.5027 (2)0.0389 (8)
C260.42421 (16)0.8003 (3)0.5022 (2)0.0374 (8)
C270.28159 (17)0.6985 (4)0.3492 (2)0.0632 (12)
H27A0.28880.73480.30610.095*
H27B0.24190.71690.34730.095*
H27C0.28430.62100.34350.095*
C280.55725 (18)0.8220 (4)0.3559 (2)0.0657 (12)
H28A0.53620.75670.33110.099*
H28B0.60000.81220.36980.099*
H28C0.54330.88190.31900.099*
C290.83703 (17)0.5201 (3)0.0916 (2)0.0480 (10)
C300.8550 (2)0.6281 (4)0.0941 (2)0.0621 (12)
C310.8204 (3)0.7101 (4)0.1074 (3)0.0879 (18)
H310.83140.78250.10550.105*
C320.7707 (3)0.6867 (5)0.1229 (3)0.097 (2)
H320.74840.74300.13300.117*
C330.7525 (2)0.5796 (5)0.1242 (3)0.0843 (16)
H330.71860.56390.13640.101*
C340.78519 (19)0.4953 (4)0.1070 (2)0.0644 (12)
H340.77250.42330.10570.077*
C350.87370 (19)0.4315 (3)0.0756 (2)0.0495 (10)
C360.87985 (16)0.0701 (3)0.2347 (2)0.0441 (9)
C370.83292 (18)−0.0038 (3)0.2274 (3)0.0509 (10)
C380.8293 (2)−0.0506 (4)0.2951 (3)0.0703 (13)
H380.7979−0.09840.29060.084*
C390.8722 (2)−0.0267 (4)0.3695 (3)0.0769 (14)
H390.8692−0.05880.41500.092*
C400.9200 (2)0.0443 (4)0.3788 (3)0.0710 (13)
H400.94920.05870.42940.085*
C410.92263 (18)0.0929 (3)0.3104 (2)0.0570 (11)
H410.95370.14170.31530.068*
C420.88268 (18)0.1215 (3)0.1610 (2)0.0460 (9)
C430.84987 (19)0.1941 (3)−0.1155 (2)0.0556 (11)
C440.8485 (2)0.1465 (4)−0.1871 (3)0.0698 (13)
H440.81200.1430−0.23110.084*
C450.8992 (2)0.1054 (4)−0.1936 (3)0.0722 (13)
H450.89730.0744−0.24190.087*
C460.9546 (2)0.1095 (3)−0.1280 (2)0.0569 (11)
C471.0111 (3)0.0680 (3)−0.1272 (3)0.0724 (14)
H471.01250.0359−0.17350.087*
C481.0621 (2)0.0744 (3)−0.0611 (3)0.0724 (14)
H481.09800.0468−0.06270.087*
C491.0621 (2)0.1227 (3)0.0115 (3)0.0582 (11)
C501.1135 (2)0.1331 (3)0.0828 (3)0.0708 (13)
H501.15060.10600.08520.085*
C511.1092 (2)0.1825 (4)0.1482 (3)0.0721 (13)
H511.14350.19020.19500.087*
C521.05307 (18)0.2222 (3)0.1457 (3)0.0544 (11)
C531.00751 (17)0.1630 (3)0.0127 (2)0.0458 (9)
C540.95339 (18)0.1572 (3)−0.0572 (2)0.0472 (10)
C550.7945 (2)0.2406 (4)−0.1093 (3)0.0784 (14)
H55A0.78850.2097−0.06360.118*
H55B0.76020.2239−0.15740.118*
H55C0.79870.3183−0.10300.118*
C561.04876 (19)0.2811 (4)0.2161 (2)0.0688 (13)
H56A1.01790.33610.19760.103*
H56B1.08700.31480.24630.103*
H56C1.03860.23030.24990.103*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cu10.0443 (3)0.0543 (3)0.0349 (3)−0.0088 (2)0.0174 (2)−0.0012 (2)
Cu20.0473 (3)0.0509 (3)0.0462 (3)0.0020 (2)0.0221 (2)−0.0010 (2)
O10.079 (2)0.090 (2)0.061 (2)0.0205 (18)0.0053 (18)−0.0111 (17)
O20.0684 (18)0.0526 (17)0.0416 (15)−0.0112 (14)0.0223 (14)−0.0057 (13)
O30.164 (4)0.076 (2)0.073 (2)0.045 (3)0.046 (2)0.0203 (19)
O40.0520 (17)0.0604 (17)0.0450 (15)−0.0038 (14)0.0180 (13)0.0105 (13)
O50.071 (2)0.0692 (19)0.0609 (18)0.0028 (15)0.0367 (16)0.0050 (15)
O60.071 (2)0.067 (2)0.074 (2)0.0095 (16)0.0252 (18)0.0059 (17)
O70.0567 (19)0.073 (2)0.085 (2)−0.0001 (16)0.0352 (17)−0.0041 (17)
O80.0611 (18)0.0504 (17)0.073 (2)0.0047 (14)0.0261 (15)−0.0054 (15)
O90.119 (3)0.066 (2)0.121 (3)−0.025 (2)0.048 (3)−0.003 (2)
O100.0480 (16)0.0677 (18)0.0506 (17)−0.0042 (14)0.0235 (13)0.0045 (14)
O110.0665 (18)0.0551 (17)0.0483 (17)0.0008 (14)0.0211 (15)−0.0071 (13)
O120.066 (2)0.0548 (19)0.079 (2)−0.0062 (15)0.0244 (18)−0.0037 (16)
N10.0407 (17)0.0423 (17)0.0376 (17)−0.0067 (14)0.0189 (14)−0.0010 (14)
N20.0404 (18)0.0444 (18)0.0396 (18)−0.0016 (14)0.0184 (14)0.0023 (14)
N30.055 (2)0.0425 (18)0.0437 (19)−0.0013 (15)0.0212 (17)0.0019 (14)
N40.0475 (19)0.0410 (18)0.050 (2)−0.0027 (14)0.0208 (17)0.0015 (15)
C10.053 (2)0.047 (2)0.055 (3)−0.0010 (19)0.033 (2)−0.006 (2)
C20.091 (4)0.058 (3)0.068 (3)0.009 (3)0.049 (3)0.003 (3)
C30.114 (5)0.047 (3)0.118 (5)−0.001 (3)0.084 (4)0.001 (3)
C40.079 (4)0.067 (3)0.108 (4)−0.017 (3)0.056 (3)−0.032 (3)
C50.058 (3)0.066 (3)0.079 (3)−0.005 (2)0.024 (2)−0.020 (3)
C60.058 (3)0.048 (2)0.060 (3)0.000 (2)0.026 (2)−0.008 (2)
C70.052 (3)0.068 (3)0.045 (3)0.008 (2)0.027 (2)−0.004 (2)
C80.050 (2)0.043 (2)0.037 (2)−0.0044 (18)0.0135 (19)−0.0027 (17)
C90.070 (3)0.046 (2)0.049 (3)−0.001 (2)0.021 (2)−0.007 (2)
C100.082 (3)0.072 (3)0.047 (3)0.014 (3)0.009 (3)0.006 (2)
C110.121 (5)0.082 (4)0.048 (3)0.018 (3)0.032 (3)0.024 (3)
C120.100 (4)0.087 (4)0.067 (3)0.004 (3)0.046 (3)0.017 (3)
C130.069 (3)0.063 (3)0.051 (3)0.000 (2)0.024 (2)0.011 (2)
C140.056 (3)0.043 (2)0.041 (2)−0.012 (2)0.016 (2)−0.0079 (18)
C150.044 (2)0.045 (2)0.048 (2)−0.0004 (18)0.0222 (19)0.0019 (18)
C160.048 (2)0.060 (3)0.063 (3)−0.003 (2)0.033 (2)0.003 (2)
C170.067 (3)0.057 (3)0.056 (3)0.005 (2)0.042 (2)0.010 (2)
C180.056 (3)0.044 (2)0.043 (2)−0.0002 (18)0.026 (2)−0.0003 (18)
C190.073 (3)0.063 (3)0.039 (2)−0.002 (2)0.026 (2)−0.001 (2)
C200.068 (3)0.069 (3)0.040 (2)−0.012 (2)0.015 (2)−0.007 (2)
C210.044 (2)0.052 (2)0.039 (2)−0.0060 (18)0.0098 (18)0.0031 (18)
C220.047 (3)0.068 (3)0.049 (3)−0.010 (2)0.005 (2)−0.001 (2)
C230.035 (2)0.079 (3)0.057 (3)−0.009 (2)0.014 (2)0.011 (2)
C240.041 (2)0.058 (3)0.048 (2)0.0000 (19)0.020 (2)0.0086 (19)
C250.043 (2)0.040 (2)0.035 (2)−0.0033 (16)0.0169 (18)0.0015 (16)
C260.044 (2)0.0333 (19)0.037 (2)0.0037 (16)0.0184 (18)0.0030 (16)
C270.042 (2)0.085 (3)0.062 (3)−0.013 (2)0.020 (2)−0.006 (2)
C280.050 (3)0.097 (3)0.060 (3)−0.005 (2)0.032 (2)0.004 (2)
C290.052 (3)0.044 (2)0.038 (2)0.0078 (19)0.0053 (19)−0.0018 (18)
C300.070 (3)0.054 (3)0.051 (3)0.003 (2)0.010 (2)−0.004 (2)
C310.105 (4)0.053 (3)0.076 (4)0.026 (3)0.000 (3)−0.013 (3)
C320.092 (4)0.092 (5)0.082 (4)0.051 (4)0.003 (3)−0.019 (3)
C330.055 (3)0.117 (5)0.073 (3)0.030 (3)0.014 (3)−0.005 (3)
C340.054 (3)0.076 (3)0.060 (3)0.013 (2)0.018 (2)0.000 (2)
C350.054 (3)0.053 (3)0.039 (2)0.006 (2)0.015 (2)0.0022 (19)
C360.046 (2)0.043 (2)0.049 (2)0.0101 (18)0.024 (2)0.0017 (18)
C370.055 (3)0.045 (2)0.063 (3)0.011 (2)0.034 (2)0.005 (2)
C380.079 (3)0.061 (3)0.088 (4)0.005 (2)0.052 (3)0.010 (3)
C390.107 (4)0.071 (3)0.078 (4)0.017 (3)0.064 (3)0.016 (3)
C400.086 (4)0.078 (3)0.051 (3)0.016 (3)0.027 (3)0.006 (2)
C410.064 (3)0.057 (3)0.054 (3)0.007 (2)0.027 (2)0.000 (2)
C420.049 (2)0.039 (2)0.057 (3)0.0128 (19)0.028 (2)−0.0004 (19)
C430.063 (3)0.056 (3)0.043 (2)0.000 (2)0.015 (2)0.003 (2)
C440.087 (4)0.070 (3)0.044 (3)0.000 (3)0.016 (3)−0.005 (2)
C450.115 (4)0.064 (3)0.042 (3)0.000 (3)0.033 (3)−0.006 (2)
C460.090 (3)0.042 (2)0.053 (3)−0.001 (2)0.043 (3)−0.001 (2)
C470.109 (4)0.050 (3)0.088 (4)0.004 (3)0.071 (3)−0.001 (3)
C480.080 (4)0.051 (3)0.116 (4)0.002 (2)0.071 (3)−0.002 (3)
C490.067 (3)0.037 (2)0.087 (3)0.001 (2)0.049 (3)0.001 (2)
C500.051 (3)0.055 (3)0.114 (4)0.005 (2)0.040 (3)0.008 (3)
C510.053 (3)0.060 (3)0.092 (4)−0.004 (2)0.014 (3)0.002 (3)
C520.047 (3)0.051 (2)0.063 (3)−0.006 (2)0.017 (2)0.004 (2)
C530.056 (3)0.032 (2)0.060 (3)−0.0012 (18)0.035 (2)0.0052 (18)
C540.062 (3)0.039 (2)0.049 (2)−0.0037 (19)0.030 (2)0.0029 (18)
C550.056 (3)0.101 (4)0.064 (3)0.003 (3)0.006 (2)−0.010 (3)
C560.060 (3)0.080 (3)0.060 (3)−0.017 (2)0.015 (2)−0.011 (2)

Geometric parameters (Å, °)

Cu1—O21.931 (2)C20—C211.436 (5)
Cu1—O41.946 (2)C20—H200.9300
Cu1—N21.994 (3)C21—C251.390 (5)
Cu1—N12.022 (3)C21—C221.396 (5)
Cu2—O101.945 (2)C22—C231.363 (5)
Cu2—O81.956 (3)C22—H220.9300
Cu2—N41.992 (3)C23—C241.405 (5)
Cu2—N32.044 (3)C23—H230.9300
O1—C71.249 (4)C24—C281.501 (5)
O2—C71.267 (4)C25—C261.431 (5)
O3—C21.350 (5)C27—H27A0.9600
O3—H30.8200C27—H27B0.9600
O4—C141.264 (4)C27—H27C0.9600
O5—C141.254 (4)C28—H28A0.9600
O6—C91.355 (5)C28—H28B0.9600
O6—H60.8200C28—H28C0.9600
O7—C351.245 (4)C29—C301.387 (6)
O8—C351.264 (4)C29—C341.395 (5)
O9—C301.351 (5)C29—C351.487 (5)
O9—H90.8200C30—C311.377 (6)
O10—C421.275 (4)C31—C321.344 (7)
O11—C421.254 (4)C31—H310.9300
O12—C371.343 (4)C32—C331.386 (8)
O12—H120.8200C32—H320.9300
N1—C151.332 (4)C33—C341.396 (6)
N1—C261.360 (4)C33—H330.9300
N2—C241.332 (4)C34—H340.9300
N2—C251.369 (4)C36—C411.384 (5)
N3—C431.339 (5)C36—C371.407 (5)
N3—C541.367 (4)C36—C421.487 (5)
N4—C521.324 (5)C37—C381.372 (5)
N4—C531.367 (4)C38—C391.372 (6)
C1—C21.392 (5)C38—H380.9300
C1—C61.394 (5)C39—C401.393 (6)
C1—C71.490 (5)C39—H390.9300
C2—C31.394 (6)C40—C411.384 (5)
C3—C41.354 (6)C40—H400.9300
C3—H3A0.9300C41—H410.9300
C4—C51.375 (6)C43—C441.397 (5)
C4—H40.9300C43—C551.479 (6)
C5—C61.373 (5)C44—C451.355 (6)
C5—H50.9300C44—H440.9300
C6—H6A0.9300C45—C461.400 (6)
C8—C131.381 (5)C45—H450.9300
C8—C91.399 (5)C46—C541.407 (5)
C8—C141.484 (5)C46—C471.434 (6)
C9—C101.392 (6)C47—C481.343 (6)
C10—C111.364 (6)C47—H470.9300
C10—H100.9300C48—C491.429 (6)
C11—C121.373 (6)C48—H480.9300
C11—H110.9300C49—C531.399 (5)
C12—C131.391 (5)C49—C501.404 (6)
C12—H12A0.9300C50—C511.356 (6)
C13—H130.9300C50—H500.9300
C15—C161.396 (5)C51—C521.407 (6)
C15—C271.504 (5)C51—H510.9300
C16—C171.350 (5)C52—C561.490 (6)
C16—H160.9300C53—C541.423 (5)
C17—C181.408 (5)C55—H55A0.9600
C17—H170.9300C55—H55B0.9600
C18—C261.399 (5)C55—H55C0.9600
C18—C191.433 (5)C56—H56A0.9600
C19—C201.346 (5)C56—H56B0.9600
C19—H190.9300C56—H56C0.9600
O2—Cu1—O491.00 (11)C21—C25—C26120.5 (3)
O2—Cu1—N2152.67 (12)N1—C26—C18123.0 (3)
O4—Cu1—N297.15 (11)N1—C26—C25117.4 (3)
O2—Cu1—N1104.90 (11)C18—C26—C25119.6 (3)
O4—Cu1—N1144.27 (11)C15—C27—H27A109.5
N2—Cu1—N183.30 (11)C15—C27—H27B109.5
O10—Cu2—O890.72 (11)H27A—C27—H27B109.5
O10—Cu2—N494.59 (12)C15—C27—H27C109.5
O8—Cu2—N4155.88 (12)H27A—C27—H27C109.5
O10—Cu2—N3143.61 (12)H27B—C27—H27C109.5
O8—Cu2—N3106.20 (12)C24—C28—H28A109.5
N4—Cu2—N382.98 (13)C24—C28—H28B109.5
C7—O2—Cu1110.6 (2)H28A—C28—H28B109.5
C2—O3—H3109.5C24—C28—H28C109.5
C14—O4—Cu1108.9 (2)H28A—C28—H28C109.5
C9—O6—H6109.5H28B—C28—H28C109.5
C35—O8—Cu2104.0 (3)C30—C29—C34119.2 (4)
C30—O9—H9109.5C30—C29—C35120.4 (4)
C42—O10—Cu2109.0 (2)C34—C29—C35120.4 (4)
C37—O12—H12109.5O9—C30—C31118.9 (5)
C15—N1—C26118.7 (3)O9—C30—C29120.9 (4)
C15—N1—Cu1130.4 (2)C31—C30—C29120.3 (5)
C26—N1—Cu1110.8 (2)C32—C31—C30120.8 (5)
C24—N2—C25118.9 (3)C32—C31—H31119.6
C24—N2—Cu1129.3 (3)C30—C31—H31119.6
C25—N2—Cu1111.8 (2)C31—C32—C33120.7 (5)
C43—N3—C54119.1 (3)C31—C32—H32119.6
C43—N3—Cu2130.4 (3)C33—C32—H32119.6
C54—N3—Cu2110.1 (2)C32—C33—C34119.5 (5)
C52—N4—C53120.1 (3)C32—C33—H33120.2
C52—N4—Cu2128.1 (3)C34—C33—H33120.2
C53—N4—Cu2111.7 (2)C29—C34—C33119.4 (5)
C2—C1—C6118.3 (4)C29—C34—H34120.3
C2—C1—C7121.2 (4)C33—C34—H34120.3
C6—C1—C7120.5 (4)O7—C35—O8121.5 (4)
O3—C2—C1121.0 (4)O7—C35—C29120.5 (4)
O3—C2—C3119.5 (5)O8—C35—C29118.0 (4)
C1—C2—C3119.5 (5)C41—C36—C37119.2 (4)
C4—C3—C2120.5 (5)C41—C36—C42121.5 (4)
C4—C3—H3A119.8C37—C36—C42119.3 (4)
C2—C3—H3A119.8O12—C37—C38117.3 (4)
C3—C4—C5121.1 (5)O12—C37—C36122.8 (4)
C3—C4—H4119.5C38—C37—C36119.9 (4)
C5—C4—H4119.5C39—C38—C37119.9 (5)
C6—C5—C4119.1 (5)C39—C38—H38120.1
C6—C5—H5120.5C37—C38—H38120.1
C4—C5—H5120.5C38—C39—C40121.7 (4)
C5—C6—C1121.5 (4)C38—C39—H39119.1
C5—C6—H6A119.3C40—C39—H39119.1
C1—C6—H6A119.3C41—C40—C39118.0 (4)
O1—C7—O2122.3 (4)C41—C40—H40121.0
O1—C7—C1119.5 (4)C39—C40—H40121.0
O2—C7—C1118.2 (4)C40—C41—C36121.2 (4)
C13—C8—C9118.6 (4)C40—C41—H41119.4
C13—C8—C14120.9 (4)C36—C41—H41119.4
C9—C8—C14120.4 (4)O11—C42—O10122.4 (4)
O6—C9—C10118.0 (4)O11—C42—C36120.1 (4)
O6—C9—C8122.2 (4)O10—C42—C36117.6 (4)
C10—C9—C8119.8 (4)N3—C43—C44120.1 (4)
C11—C10—C9120.5 (4)N3—C43—C55119.0 (4)
C11—C10—H10119.7C44—C43—C55120.9 (4)
C9—C10—H10119.7C45—C44—C43121.3 (4)
C10—C11—C12120.5 (4)C45—C44—H44119.3
C10—C11—H11119.7C43—C44—H44119.3
C12—C11—H11119.7C44—C45—C46120.3 (4)
C11—C12—C13119.6 (5)C44—C45—H45119.9
C11—C12—H12A120.2C46—C45—H45119.9
C13—C12—H12A120.2C45—C46—C54116.2 (4)
C8—C13—C12121.0 (4)C45—C46—C47125.5 (4)
C8—C13—H13119.5C54—C46—C47118.3 (4)
C12—C13—H13119.5C48—C47—C46121.6 (4)
O5—C14—O4122.8 (4)C48—C47—H47119.2
O5—C14—C8119.8 (4)C46—C47—H47119.2
O4—C14—C8117.4 (4)C47—C48—C49121.2 (4)
N1—C15—C16121.0 (3)C47—C48—H48119.4
N1—C15—C27118.5 (3)C49—C48—H48119.4
C16—C15—C27120.4 (3)C53—C49—C50116.9 (4)
C17—C16—C15121.0 (4)C53—C49—C48118.4 (4)
C17—C16—H16119.5C50—C49—C48124.7 (4)
C15—C16—H16119.5C51—C50—C49120.2 (4)
C16—C17—C18119.5 (4)C51—C50—H50119.9
C16—C17—H17120.3C49—C50—H50119.9
C18—C17—H17120.3C50—C51—C52120.3 (4)
C26—C18—C17116.9 (3)C50—C51—H51119.8
C26—C18—C19118.7 (4)C52—C51—H51119.8
C17—C18—C19124.5 (4)N4—C52—C51120.3 (4)
C20—C19—C18121.7 (4)N4—C52—C56119.3 (4)
C20—C19—H19119.2C51—C52—C56120.4 (4)
C18—C19—H19119.2N4—C53—C49122.0 (4)
C19—C20—C21120.5 (4)N4—C53—C54117.3 (3)
C19—C20—H20119.8C49—C53—C54120.7 (4)
C21—C20—H20119.8N3—C54—C46123.1 (4)
C25—C21—C22117.4 (4)N3—C54—C53117.2 (3)
C25—C21—C20119.0 (3)C46—C54—C53119.7 (4)
C22—C21—C20123.6 (4)C43—C55—H55A109.5
C23—C22—C21119.3 (4)C43—C55—H55B109.5
C23—C22—H22120.3H55A—C55—H55B109.5
C21—C22—H22120.3C43—C55—H55C109.5
C22—C23—C24121.0 (4)H55A—C55—H55C109.5
C22—C23—H23119.5H55B—C55—H55C109.5
C24—C23—H23119.5C52—C56—H56A109.5
N2—C24—C23120.2 (4)C52—C56—H56B109.5
N2—C24—C28119.0 (3)H56A—C56—H56B109.5
C23—C24—C28120.7 (3)C52—C56—H56C109.5
N2—C25—C21123.0 (3)H56A—C56—H56C109.5
N2—C25—C26116.6 (3)H56B—C56—H56C109.5
O4—Cu1—O2—C7141.8 (3)C24—N2—C25—C26−176.5 (3)
N2—Cu1—O2—C734.1 (4)Cu1—N2—C25—C264.6 (4)
N1—Cu1—O2—C7−70.5 (3)C22—C21—C25—N20.2 (5)
O2—Cu1—O4—C1483.0 (2)C20—C21—C25—N2−178.6 (3)
N2—Cu1—O4—C14−123.1 (2)C22—C21—C25—C26−179.8 (3)
N1—Cu1—O4—C14−34.7 (3)C20—C21—C25—C261.4 (5)
O10—Cu2—O8—C35104.0 (2)C15—N1—C26—C180.5 (5)
N4—Cu2—O8—C351.0 (4)Cu1—N1—C26—C18177.7 (3)
N3—Cu2—O8—C35−108.7 (2)C15—N1—C26—C25−177.9 (3)
O8—Cu2—O10—C4275.4 (2)Cu1—N1—C26—C25−0.7 (4)
N4—Cu2—O10—C42−128.2 (2)C17—C18—C26—N11.5 (5)
N3—Cu2—O10—C42−43.8 (3)C19—C18—C26—N1−178.9 (3)
O2—Cu1—N1—C15−27.3 (3)C17—C18—C26—C25179.8 (3)
O4—Cu1—N1—C1586.4 (3)C19—C18—C26—C25−0.6 (5)
N2—Cu1—N1—C15179.3 (3)N2—C25—C26—N1−2.7 (5)
O2—Cu1—N1—C26155.9 (2)C21—C25—C26—N1177.4 (3)
O4—Cu1—N1—C26−90.4 (3)N2—C25—C26—C18178.9 (3)
N2—Cu1—N1—C262.5 (2)C21—C25—C26—C18−1.1 (5)
O2—Cu1—N2—C2467.7 (4)C34—C29—C30—O9176.9 (4)
O4—Cu1—N2—C24−38.6 (3)C35—C29—C30—O9−1.1 (6)
N1—Cu1—N2—C24177.4 (3)C34—C29—C30—C31−3.3 (6)
O2—Cu1—N2—C25−113.6 (3)C35—C29—C30—C31178.7 (4)
O4—Cu1—N2—C25140.1 (2)O9—C30—C31—C32−176.1 (5)
N1—Cu1—N2—C25−3.9 (2)C29—C30—C31—C324.0 (7)
O10—Cu2—N3—C4391.7 (4)C30—C31—C32—C33−1.5 (8)
O8—Cu2—N3—C43−22.9 (4)C31—C32—C33—C34−1.6 (8)
N4—Cu2—N3—C43179.9 (3)C30—C29—C34—C330.2 (6)
O10—Cu2—N3—C54−81.1 (3)C35—C29—C34—C33178.1 (4)
O8—Cu2—N3—C54164.3 (2)C32—C33—C34—C292.3 (7)
N4—Cu2—N3—C547.1 (2)Cu2—O8—C35—O78.9 (4)
O10—Cu2—N4—C52−40.7 (3)Cu2—O8—C35—C29−169.2 (3)
O8—Cu2—N4—C5261.4 (5)C30—C29—C35—O713.4 (6)
N3—Cu2—N4—C52175.8 (3)C34—C29—C35—O7−164.5 (4)
O10—Cu2—N4—C53136.2 (2)C30—C29—C35—O8−168.4 (4)
O8—Cu2—N4—C53−121.6 (3)C34—C29—C35—O813.7 (5)
N3—Cu2—N4—C53−7.3 (2)C41—C36—C37—O12−178.0 (3)
C6—C1—C2—O3177.9 (4)C42—C36—C37—O121.6 (5)
C7—C1—C2—O3−0.8 (6)C41—C36—C37—C381.4 (5)
C6—C1—C2—C3−2.7 (6)C42—C36—C37—C38−179.0 (3)
C7—C1—C2—C3178.7 (4)O12—C37—C38—C39178.1 (4)
O3—C2—C3—C4−177.4 (5)C36—C37—C38—C39−1.3 (6)
C1—C2—C3—C43.2 (7)C37—C38—C39—C40−0.1 (7)
C2—C3—C4—C5−1.7 (7)C38—C39—C40—C411.4 (7)
C3—C4—C5—C6−0.3 (7)C39—C40—C41—C36−1.3 (6)
C4—C5—C6—C10.7 (6)C37—C36—C41—C40−0.1 (6)
C2—C1—C6—C50.7 (6)C42—C36—C41—C40−179.6 (4)
C7—C1—C6—C5179.4 (4)Cu2—O10—C42—O110.7 (4)
Cu1—O2—C7—O1−3.1 (5)Cu2—O10—C42—C36−179.8 (2)
Cu1—O2—C7—C1175.1 (3)C41—C36—C42—O11178.5 (3)
C2—C1—C7—O15.6 (6)C37—C36—C42—O11−1.1 (5)
C6—C1—C7—O1−173.1 (4)C41—C36—C42—O10−1.0 (5)
C2—C1—C7—O2−172.7 (4)C37—C36—C42—O10179.4 (3)
C6—C1—C7—O28.7 (5)C54—N3—C43—C440.8 (6)
C13—C8—C9—O6−178.6 (4)Cu2—N3—C43—C44−171.4 (3)
C14—C8—C9—O64.4 (5)C54—N3—C43—C55−178.9 (4)
C13—C8—C9—C101.6 (6)Cu2—N3—C43—C558.8 (6)
C14—C8—C9—C10−175.5 (3)N3—C43—C44—C45−0.8 (7)
O6—C9—C10—C11179.4 (4)C55—C43—C44—C45178.9 (4)
C8—C9—C10—C11−0.8 (6)C43—C44—C45—C460.3 (7)
C9—C10—C11—C12−0.7 (8)C44—C45—C46—C540.3 (6)
C10—C11—C12—C131.4 (8)C44—C45—C46—C47179.4 (4)
C9—C8—C13—C12−1.0 (6)C45—C46—C47—C48−179.4 (4)
C14—C8—C13—C12176.1 (4)C54—C46—C47—C48−0.3 (6)
C11—C12—C13—C8−0.5 (7)C46—C47—C48—C490.2 (7)
Cu1—O4—C14—O59.1 (4)C47—C48—C49—C530.4 (6)
Cu1—O4—C14—C8−170.0 (2)C47—C48—C49—C50−179.6 (4)
C13—C8—C14—O5173.0 (4)C53—C49—C50—C51−1.4 (6)
C9—C8—C14—O5−9.9 (5)C48—C49—C50—C51178.5 (4)
C13—C8—C14—O4−7.8 (5)C49—C50—C51—C521.0 (7)
C9—C8—C14—O4169.2 (3)C53—N4—C52—C51−3.6 (6)
C26—N1—C15—C16−1.6 (5)Cu2—N4—C52—C51173.1 (3)
Cu1—N1—C15—C16−178.2 (3)C53—N4—C52—C56175.1 (3)
C26—N1—C15—C27176.9 (3)Cu2—N4—C52—C56−8.2 (5)
Cu1—N1—C15—C270.3 (5)C50—C51—C52—N41.6 (6)
N1—C15—C16—C170.7 (6)C50—C51—C52—C56−177.2 (4)
C27—C15—C16—C17−177.7 (4)C52—N4—C53—C493.2 (5)
C15—C16—C17—C181.3 (6)Cu2—N4—C53—C49−174.0 (3)
C16—C17—C18—C26−2.3 (5)C52—N4—C53—C54−176.5 (3)
C16—C17—C18—C19178.1 (4)Cu2—N4—C53—C546.2 (4)
C26—C18—C19—C202.0 (6)C50—C49—C53—N4−0.6 (5)
C17—C18—C19—C20−178.4 (4)C48—C49—C53—N4179.4 (3)
C18—C19—C20—C21−1.7 (6)C50—C49—C53—C54179.1 (3)
C19—C20—C21—C250.0 (6)C48—C49—C53—C54−0.9 (5)
C19—C20—C21—C22−178.7 (4)C43—N3—C54—C46−0.2 (5)
C25—C21—C22—C23−2.4 (6)Cu2—N3—C54—C46173.5 (3)
C20—C21—C22—C23176.3 (4)C43—N3—C54—C53−179.6 (3)
C21—C22—C23—C241.1 (6)Cu2—N3—C54—C53−5.9 (4)
C25—N2—C24—C23−4.8 (5)C45—C46—C54—N3−0.4 (5)
Cu1—N2—C24—C23173.8 (3)C47—C46—C54—N3−179.5 (3)
C25—N2—C24—C28174.4 (3)C45—C46—C54—C53179.0 (4)
Cu1—N2—C24—C28−7.0 (5)C47—C46—C54—C53−0.2 (5)
C22—C23—C24—N22.6 (6)N4—C53—C54—N3−0.1 (5)
C22—C23—C24—C28−176.5 (4)C49—C53—C54—N3−179.9 (3)
C24—N2—C25—C213.4 (5)N4—C53—C54—C46−179.5 (3)
Cu1—N2—C25—C21−175.4 (3)C49—C53—C54—C460.7 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O12—H12···O110.821.822.549 (4)147
O9—H9···O70.821.842.561 (4)146
O6—H6···O50.821.852.572 (4)146
O3—H3···O10.821.822.553 (5)148

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2438).

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