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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): m1047.
Published online 2009 August 8. doi:  10.1107/S1600536809030463
PMCID: PMC2970041

{N′-[(E)-(5-Bromo-2-oxidophen­yl)(phen­yl)methyl­ene]benzohydrazidato}pyridine­copper(II)

Abstract

The asymmetric unit of title complex, [Cu(C20H13BrN2O2)(C5H5N)], contains two independent mol­ecules. In each mol­ecule, the central CuII atom has a square-planar environment formed by the tridentate hydrazone and the monodentate pyridine ligands, with the N atoms in a trans arrangement about the CuII atom.

Related literature

For the isostructural Ni complex, see: Zheng et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1047-scheme1.jpg

Experimental

Crystal data

  • [Cu(C20H13BrN2O2)(C5H5N)]
  • M r = 535.87
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1047-efi1.jpg
  • a = 22.655 (2) Å
  • b = 10.6514 (10) Å
  • c = 19.3388 (19) Å
  • β = 108.521 (2)°
  • V = 4424.9 (7) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 2.82 mm−1
  • T = 295 K
  • 0.16 × 0.12 × 0.08 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.661, T max = 0.806
  • 22878 measured reflections
  • 7831 independent reflections
  • 5740 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.100
  • S = 1.09
  • 7831 reflections
  • 577 parameters
  • H-atom parameters constrained
  • Δρmax = 0.46 e Å−3
  • Δρmin = −0.57 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [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: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809030463/rk2158sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030463/rk2158Isup2.hkl

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

Acknowledgments

This project was supported by the Postgraduate Foundation of Xi’an Polytechnic University (No. Y05-2-09)

supplementary crystallographic information

Comment

This structure was solved in continue the investigation of complexes of transition metals (Ni) with ligands {N-[(E)-(5-bromo-2- -hydroxyphenyl)(phenyl)methylene]benzohydrazide}pyridinenickel(II) (Zheng et al., 2009). These Ni- and Cu-complexes (Fig.1) are isostructural. All bond distances and bond angles have a normal values.

Experimental

A DMF solution (5 ml) of N-[(E)-(5-bromo-2- hydroxyphenyl)(phenyl)methylene]benzohydrazide (0.25 mmol, 0.099 g) was mixed with a methanol solution(5 ml) of CuCl2.2H2O (0.25 mmol, 0.043 g). The mixture was stirred at 298 K for 4 h and then filtered. A blue precipitate was produced after about 10 d. A pyridine mixture (5 ml) was used to dissolve the precipitate at 330 K. Blue block-shaped crystals of were obtained after one month (yield 30%).

Refinement

All H atoms were placed geometrically at ideal positions and allowed to ride on the parent C atoms, with C–H = 0.93 Å and Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The asymmetric unit of title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.

Crystal data

[Cu(C20H13BrN2O2)(C5H5N)]F(000) = 2152
Mr = 535.87Dx = 1.609 Mg m3
Monoclinic, P21/cMelting point: 330 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 22.655 (2) ÅCell parameters from 5857 reflections
b = 10.6514 (10) Åθ = 2.2–26.2°
c = 19.3388 (19) ŵ = 2.82 mm1
β = 108.521 (2)°T = 295 K
V = 4424.9 (7) Å3Block, blue
Z = 80.16 × 0.12 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer7831 independent reflections
Radiation source: fine-focus sealed tube5740 reflections with I > 2σ(I)
graphiteRint = 0.029
[var phi] and ω scansθmax = 25.1°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −26→26
Tmin = 0.661, Tmax = 0.806k = −12→12
22878 measured reflectionsl = −23→18

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 1.09w = 1/[σ2(Fo2) + (0.0541P)2] where P = (Fo2 + 2Fc2)/3
7831 reflections(Δ/σ)max = 0.001
577 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = −0.57 e Å3

Special details

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)

xyzUiso*/Ueq
Cu10.448059 (18)0.58286 (3)0.36047 (2)0.04049 (12)
Cu20.06456 (2)0.19326 (4)0.09827 (2)0.04655 (13)
Br10.756186 (18)0.42943 (4)0.61827 (2)0.06374 (14)
Br20.08695 (2)−0.23047 (4)−0.19252 (2)0.06763 (14)
O10.51513 (10)0.65304 (19)0.43260 (13)0.0470 (6)
O20.37982 (10)0.4965 (2)0.29422 (12)0.0442 (5)
O30.03949 (12)0.1747 (2)−0.00216 (13)0.0574 (7)
O40.09937 (12)0.2097 (2)0.20165 (13)0.0561 (6)
N10.44828 (13)0.3300 (2)0.32130 (15)0.0437 (7)
N20.48543 (12)0.4188 (2)0.36919 (14)0.0386 (6)
N30.14631 (13)0.0215 (3)0.18986 (14)0.0469 (7)
N40.11394 (12)0.0421 (3)0.11583 (14)0.0423 (7)
N50.40778 (13)0.7504 (2)0.33205 (15)0.0424 (7)
N60.01464 (13)0.3501 (3)0.08826 (16)0.0467 (7)
C10.56516 (15)0.5958 (3)0.47237 (17)0.0364 (7)
C20.57943 (14)0.4665 (3)0.46661 (17)0.0376 (7)
C30.63679 (15)0.4215 (3)0.51111 (18)0.0417 (8)
H30.64710.33810.50660.050*
C40.67815 (14)0.4958 (3)0.56095 (18)0.0433 (8)
C50.66359 (17)0.6198 (3)0.56923 (19)0.0475 (9)
H50.69120.67030.60390.057*
C60.60845 (16)0.6672 (3)0.52612 (19)0.0449 (8)
H60.59900.75050.53250.054*
C70.53780 (15)0.3801 (3)0.41444 (18)0.0375 (7)
C80.55608 (14)0.2454 (3)0.41456 (18)0.0373 (8)
C90.57715 (17)0.1986 (3)0.3606 (2)0.0530 (9)
H90.57790.24980.32190.064*
C100.59715 (18)0.0761 (4)0.3635 (2)0.0638 (11)
H100.61210.04550.32710.077*
C110.59528 (18)−0.0013 (4)0.4196 (2)0.0613 (11)
H110.6090−0.08400.42150.074*
C120.5731 (2)0.0446 (3)0.4724 (2)0.0658 (11)
H120.5711−0.00740.51020.079*
C130.55368 (17)0.1672 (3)0.4700 (2)0.0507 (9)
H130.53880.19750.50640.061*
C140.44054 (18)0.8571 (3)0.3428 (2)0.0542 (10)
H140.48360.85250.36290.065*
C150.4137 (2)0.9730 (3)0.3254 (2)0.0645 (11)
H150.43801.04530.33420.077*
C160.3504 (2)0.9803 (4)0.2948 (2)0.0681 (12)
H160.33081.05790.28350.082*
C170.31676 (19)0.8725 (4)0.2812 (2)0.0644 (11)
H170.27390.87530.25860.077*
C180.34619 (17)0.7597 (3)0.3008 (2)0.0539 (10)
H180.32240.68670.29210.065*
C190.39589 (15)0.3824 (3)0.28524 (18)0.0390 (8)
C200.35050 (15)0.3070 (3)0.22877 (18)0.0396 (8)
C210.36878 (18)0.2208 (3)0.1867 (2)0.0511 (9)
H210.41090.20650.19470.061*
C220.3249 (2)0.1554 (4)0.1325 (2)0.0626 (11)
H220.33750.09770.10400.075*
C230.2631 (2)0.1753 (4)0.1210 (2)0.0632 (11)
H230.23370.13130.08440.076*
C240.24391 (18)0.2598 (4)0.1628 (2)0.0616 (11)
H240.20170.27160.15530.074*
C250.28738 (16)0.3275 (3)0.21613 (19)0.0482 (9)
H250.27440.38680.24350.058*
C260.05294 (16)0.0824 (3)−0.03941 (18)0.0444 (8)
C270.09257 (14)−0.0200 (3)−0.00941 (17)0.0396 (8)
C280.10089 (16)−0.1110 (3)−0.05787 (18)0.0431 (8)
H280.1266−0.1794−0.03940.052*
C290.07243 (16)−0.1022 (3)−0.13131 (18)0.0448 (8)
C300.03406 (17)−0.0032 (3)−0.16105 (19)0.0511 (9)
H300.01460.0021−0.21110.061*
C310.02517 (17)0.0870 (3)−0.11555 (19)0.0523 (9)
H31−0.00040.1548−0.13570.063*
C320.12314 (15)−0.0372 (3)0.06895 (18)0.0411 (8)
C330.16432 (15)−0.1486 (3)0.09448 (17)0.0422 (8)
C340.14936 (18)−0.2398 (3)0.1365 (2)0.0545 (10)
H340.1143−0.23060.15110.065*
C350.1865 (2)−0.3456 (4)0.1570 (2)0.0683 (12)
H350.1760−0.40740.18500.082*
C360.2384 (2)−0.3594 (4)0.1361 (2)0.0724 (12)
H360.2632−0.43060.14980.087*
C370.2538 (2)−0.2684 (4)0.0954 (2)0.0683 (12)
H370.2891−0.27760.08120.082*
C380.21764 (17)−0.1639 (3)0.0751 (2)0.0530 (9)
H380.2290−0.10200.04790.064*
C390.13458 (16)0.1139 (4)0.22802 (19)0.0472 (9)
C400.16633 (16)0.1121 (4)0.30833 (19)0.0492 (9)
C410.19493 (19)0.0057 (4)0.3430 (2)0.0632 (11)
H410.1939−0.06740.31630.076*
C420.2255 (2)0.0061 (5)0.4175 (2)0.0819 (14)
H420.2447−0.06650.44090.098*
C430.2271 (2)0.1147 (5)0.4568 (2)0.0819 (14)
H430.24790.11610.50670.098*
C440.1983 (2)0.2194 (5)0.4226 (2)0.0745 (13)
H440.19940.29230.44940.089*
C450.16749 (18)0.2197 (4)0.3487 (2)0.0610 (10)
H450.14750.29210.32600.073*
C46−0.03592 (16)0.3678 (3)0.0300 (2)0.0505 (9)
H46−0.04540.3083−0.00720.061*
C47−0.07398 (18)0.4696 (4)0.0230 (2)0.0573 (10)
H47−0.10950.4774−0.01730.069*
C48−0.0591 (2)0.5604 (4)0.0763 (2)0.0661 (11)
H48−0.08400.63120.07250.079*
C49−0.0072 (2)0.5442 (4)0.1347 (2)0.0663 (12)
H490.00430.60510.17100.080*
C500.02816 (19)0.4389 (3)0.1403 (2)0.0587 (10)
H500.06280.42820.18140.070*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cu10.0447 (2)0.0330 (2)0.0410 (2)−0.00132 (18)0.00960 (19)−0.00144 (18)
Cu20.0528 (3)0.0488 (3)0.0367 (2)0.0020 (2)0.0122 (2)−0.0052 (2)
Br10.0474 (2)0.0744 (3)0.0589 (3)0.00269 (19)0.00196 (19)0.0008 (2)
Br20.0839 (3)0.0733 (3)0.0418 (2)0.0172 (2)0.0144 (2)−0.0132 (2)
O10.0473 (14)0.0341 (12)0.0517 (14)0.0019 (11)0.0044 (12)−0.0080 (11)
O20.0460 (13)0.0347 (12)0.0447 (13)0.0008 (10)0.0042 (11)−0.0020 (11)
O30.0793 (18)0.0525 (15)0.0384 (14)0.0205 (13)0.0158 (13)−0.0018 (12)
O40.0665 (17)0.0606 (16)0.0377 (14)0.0078 (14)0.0118 (12)−0.0078 (12)
N10.0463 (17)0.0344 (14)0.0448 (17)−0.0022 (13)0.0065 (14)−0.0063 (13)
N20.0412 (16)0.0334 (14)0.0377 (15)−0.0024 (13)0.0075 (13)−0.0035 (13)
N30.0518 (18)0.0538 (18)0.0311 (15)−0.0030 (14)0.0073 (13)−0.0025 (14)
N40.0470 (17)0.0462 (16)0.0315 (15)−0.0017 (13)0.0096 (13)0.0008 (13)
N50.0488 (18)0.0361 (15)0.0393 (16)−0.0018 (13)0.0099 (14)0.0008 (13)
N60.0538 (18)0.0469 (17)0.0410 (17)−0.0006 (14)0.0174 (15)−0.0050 (14)
C10.0395 (19)0.0353 (17)0.0364 (18)−0.0045 (15)0.0149 (15)−0.0033 (15)
C20.0386 (18)0.0414 (18)0.0334 (17)−0.0016 (15)0.0125 (15)−0.0003 (15)
C30.044 (2)0.0413 (18)0.0403 (19)−0.0010 (16)0.0143 (16)−0.0009 (16)
C40.0352 (18)0.055 (2)0.0380 (19)−0.0030 (16)0.0089 (15)0.0013 (17)
C50.052 (2)0.048 (2)0.040 (2)−0.0154 (17)0.0117 (17)−0.0066 (17)
C60.053 (2)0.0357 (18)0.045 (2)−0.0033 (16)0.0144 (18)−0.0049 (17)
C70.0431 (19)0.0351 (17)0.0372 (18)−0.0024 (15)0.0171 (16)0.0001 (15)
C80.0343 (18)0.0387 (18)0.0377 (19)−0.0014 (14)0.0096 (15)−0.0062 (15)
C90.061 (2)0.055 (2)0.045 (2)−0.0011 (19)0.0192 (19)−0.0056 (19)
C100.065 (3)0.063 (3)0.069 (3)0.002 (2)0.031 (2)−0.028 (2)
C110.060 (3)0.038 (2)0.080 (3)0.0075 (18)0.014 (2)−0.016 (2)
C120.091 (3)0.042 (2)0.070 (3)0.009 (2)0.033 (2)0.005 (2)
C130.068 (2)0.041 (2)0.048 (2)0.0050 (18)0.0250 (19)−0.0056 (18)
C140.057 (2)0.042 (2)0.055 (2)−0.0080 (18)0.0061 (19)−0.0007 (18)
C150.084 (3)0.036 (2)0.065 (3)−0.005 (2)0.012 (2)0.005 (2)
C160.089 (3)0.042 (2)0.073 (3)0.013 (2)0.027 (3)0.013 (2)
C170.060 (3)0.060 (3)0.073 (3)0.013 (2)0.020 (2)0.007 (2)
C180.051 (2)0.044 (2)0.065 (3)−0.0008 (18)0.016 (2)0.0023 (19)
C190.043 (2)0.0373 (18)0.0363 (18)−0.0040 (15)0.0126 (16)0.0039 (15)
C200.048 (2)0.0332 (17)0.0360 (18)−0.0062 (15)0.0105 (15)0.0059 (15)
C210.058 (2)0.047 (2)0.051 (2)−0.0079 (18)0.0209 (19)−0.0020 (18)
C220.089 (3)0.056 (2)0.045 (2)−0.018 (2)0.024 (2)−0.011 (2)
C230.076 (3)0.057 (2)0.045 (2)−0.028 (2)0.003 (2)−0.001 (2)
C240.047 (2)0.059 (2)0.068 (3)−0.0107 (19)0.003 (2)0.007 (2)
C250.052 (2)0.0404 (19)0.048 (2)−0.0026 (17)0.0108 (18)0.0028 (17)
C260.053 (2)0.046 (2)0.0371 (19)0.0000 (17)0.0172 (17)−0.0018 (17)
C270.044 (2)0.0424 (19)0.0334 (18)−0.0050 (16)0.0133 (15)0.0017 (16)
C280.049 (2)0.0423 (19)0.0366 (19)0.0045 (16)0.0113 (16)0.0001 (16)
C290.053 (2)0.049 (2)0.0333 (18)0.0008 (17)0.0139 (16)−0.0054 (16)
C300.059 (2)0.062 (2)0.0304 (19)0.0053 (19)0.0116 (17)−0.0001 (18)
C310.060 (2)0.054 (2)0.039 (2)0.0149 (19)0.0110 (18)0.0039 (18)
C320.044 (2)0.0421 (18)0.0367 (19)−0.0042 (16)0.0123 (16)−0.0025 (16)
C330.049 (2)0.0428 (19)0.0301 (18)−0.0017 (16)0.0056 (16)−0.0021 (16)
C340.057 (2)0.057 (2)0.045 (2)−0.0047 (19)0.0089 (18)0.0064 (19)
C350.084 (3)0.055 (3)0.053 (3)−0.003 (2)0.005 (2)0.013 (2)
C360.073 (3)0.058 (3)0.069 (3)0.017 (2)−0.002 (2)0.011 (2)
C370.060 (3)0.072 (3)0.064 (3)0.018 (2)0.009 (2)0.002 (2)
C380.057 (2)0.053 (2)0.046 (2)0.0052 (19)0.0114 (18)0.0077 (18)
C390.046 (2)0.059 (2)0.036 (2)−0.0102 (18)0.0132 (17)−0.0064 (18)
C400.049 (2)0.061 (2)0.037 (2)−0.0136 (18)0.0136 (17)−0.0046 (19)
C410.070 (3)0.072 (3)0.045 (2)−0.002 (2)0.016 (2)−0.002 (2)
C420.086 (3)0.100 (4)0.051 (3)0.006 (3)0.009 (2)0.005 (3)
C430.073 (3)0.124 (4)0.039 (2)−0.017 (3)0.005 (2)−0.010 (3)
C440.087 (3)0.086 (3)0.047 (3)−0.027 (3)0.017 (2)−0.018 (3)
C450.066 (3)0.070 (3)0.043 (2)−0.019 (2)0.0124 (19)−0.009 (2)
C460.051 (2)0.054 (2)0.047 (2)−0.0056 (19)0.0173 (19)−0.0084 (19)
C470.051 (2)0.062 (2)0.057 (2)0.007 (2)0.0148 (19)0.002 (2)
C480.086 (3)0.056 (2)0.065 (3)0.014 (2)0.036 (3)0.004 (2)
C490.105 (4)0.046 (2)0.049 (2)0.004 (2)0.027 (3)−0.0089 (19)
C500.076 (3)0.058 (2)0.039 (2)−0.004 (2)0.0144 (19)−0.0071 (19)

Geometric parameters (Å, °)

Cu1—O11.862 (2)C19—C201.477 (4)
Cu1—O21.903 (2)C20—C211.375 (5)
Cu1—N21.925 (2)C20—C251.389 (5)
Cu1—N52.000 (3)C21—C221.382 (5)
Cu2—O31.853 (2)C21—H210.9300
Cu2—O41.910 (2)C22—C231.363 (6)
Cu2—N41.928 (3)C22—H220.9300
Cu2—N61.993 (3)C23—C241.370 (6)
Br1—C41.900 (3)C23—H230.9300
Br2—C291.903 (3)C24—C251.381 (5)
O1—C11.302 (4)C24—H240.9300
O2—C191.296 (4)C25—H250.9300
O3—C261.310 (4)C26—C311.406 (5)
O4—C391.296 (4)C26—C271.415 (4)
N1—C191.296 (4)C27—C281.402 (4)
N1—N21.402 (3)C27—C321.464 (4)
N2—C71.298 (4)C28—C291.364 (5)
N3—C391.307 (4)C28—H280.9300
N3—N41.403 (4)C29—C301.371 (5)
N4—C321.304 (4)C30—C311.361 (5)
N5—C181.337 (4)C30—H300.9300
N5—C141.338 (4)C31—H310.9300
N6—C461.341 (4)C32—C331.493 (5)
N6—C501.343 (4)C33—C341.376 (5)
C1—C61.405 (4)C33—C381.383 (5)
C1—C21.427 (4)C34—C351.386 (5)
C2—C31.396 (4)C34—H340.9300
C2—C71.466 (4)C35—C361.368 (6)
C3—C41.364 (4)C35—H350.9300
C3—H30.9300C36—C371.362 (6)
C4—C51.382 (5)C36—H360.9300
C5—C61.360 (5)C37—C381.363 (5)
C5—H50.9300C37—H370.9300
C6—H60.9300C38—H380.9300
C7—C81.493 (4)C39—C401.490 (5)
C8—C91.372 (5)C40—C411.370 (5)
C8—C131.373 (5)C40—C451.382 (5)
C9—C101.376 (5)C41—C421.387 (6)
C9—H90.9300C41—H410.9300
C10—C111.374 (6)C42—C431.378 (6)
C10—H100.9300C42—H420.9300
C11—C121.364 (5)C43—C441.353 (6)
C11—H110.9300C43—H430.9300
C12—C131.374 (5)C44—C451.376 (6)
C12—H120.9300C44—H440.9300
C13—H130.9300C45—H450.9300
C14—C151.370 (5)C46—C471.365 (5)
C14—H140.9300C46—H460.9300
C15—C161.367 (5)C47—C481.376 (5)
C15—H150.9300C47—H470.9300
C16—C171.358 (5)C48—C491.358 (6)
C16—H160.9300C48—H480.9300
C17—C181.368 (5)C49—C501.363 (5)
C17—H170.9300C49—H490.9300
C18—H180.9300C50—H500.9300
O1—Cu1—O2173.64 (10)C20—C21—C22120.4 (4)
O1—Cu1—N293.85 (10)C20—C21—H21119.8
O2—Cu1—N282.00 (10)C22—C21—H21119.8
O1—Cu1—N592.31 (10)C23—C22—C21120.0 (4)
O2—Cu1—N592.53 (10)C23—C22—H22120.0
N2—Cu1—N5169.48 (11)C21—C22—H22120.0
O3—Cu2—O4173.82 (11)C22—C23—C24120.5 (4)
O3—Cu2—N493.61 (11)C22—C23—H23119.8
O4—Cu2—N482.44 (11)C24—C23—H23119.8
O3—Cu2—N690.70 (11)C23—C24—C25119.9 (4)
O4—Cu2—N693.32 (11)C23—C24—H24120.0
N4—Cu2—N6175.65 (12)C25—C24—H24120.0
C1—O1—Cu1127.20 (19)C24—C25—C20120.0 (4)
C19—O2—Cu1109.9 (2)C24—C25—H25120.0
C26—O3—Cu2127.5 (2)C20—C25—H25120.0
C39—O4—Cu2109.7 (2)O3—C26—C31116.4 (3)
C19—N1—N2108.7 (3)O3—C26—C27125.5 (3)
C7—N2—N1117.4 (3)C31—C26—C27118.1 (3)
C7—N2—Cu1129.0 (2)C28—C27—C26117.5 (3)
N1—N2—Cu1113.54 (19)C28—C27—C32119.0 (3)
C39—N3—N4108.9 (3)C26—C27—C32123.4 (3)
C32—N4—N3117.5 (3)C29—C28—C27122.0 (3)
C32—N4—Cu2129.1 (2)C29—C28—H28119.0
N3—N4—Cu2113.3 (2)C27—C28—H28119.0
C18—N5—C14117.1 (3)C28—C29—C30121.1 (3)
C18—N5—Cu1120.7 (2)C28—C29—Br2118.7 (3)
C14—N5—Cu1122.3 (2)C30—C29—Br2120.2 (3)
C46—N6—C50117.5 (3)C31—C30—C29118.5 (3)
C46—N6—Cu2120.4 (2)C31—C30—H30120.8
C50—N6—Cu2122.0 (3)C29—C30—H30120.8
O1—C1—C6117.1 (3)C30—C31—C26122.9 (3)
O1—C1—C2125.6 (3)C30—C31—H31118.5
C6—C1—C2117.3 (3)C26—C31—H31118.5
C3—C2—C1118.2 (3)N4—C32—C27120.7 (3)
C3—C2—C7118.6 (3)N4—C32—C33120.4 (3)
C1—C2—C7123.2 (3)C27—C32—C33118.8 (3)
C4—C3—C2122.2 (3)C34—C33—C38118.4 (3)
C4—C3—H3118.9C34—C33—C32120.7 (3)
C2—C3—H3118.9C38—C33—C32120.8 (3)
C3—C4—C5120.0 (3)C33—C34—C35120.2 (4)
C3—C4—Br1119.9 (3)C33—C34—H34119.9
C5—C4—Br1120.0 (3)C35—C34—H34119.9
C6—C5—C4119.3 (3)C36—C35—C34120.2 (4)
C6—C5—H5120.3C36—C35—H35119.9
C4—C5—H5120.3C34—C35—H35119.9
C5—C6—C1122.8 (3)C37—C36—C35119.7 (4)
C5—C6—H6118.6C37—C36—H36120.1
C1—C6—H6118.6C35—C36—H36120.1
N2—C7—C2121.0 (3)C36—C37—C38120.4 (4)
N2—C7—C8120.0 (3)C36—C37—H37119.8
C2—C7—C8119.0 (3)C38—C37—H37119.8
C9—C8—C13118.9 (3)C37—C38—C33121.0 (4)
C9—C8—C7120.8 (3)C37—C38—H38119.5
C13—C8—C7120.3 (3)C33—C38—H38119.5
C8—C9—C10120.2 (4)O4—C39—N3125.5 (3)
C8—C9—H9119.9O4—C39—C40117.0 (3)
C10—C9—H9119.9N3—C39—C40117.5 (3)
C11—C10—C9120.6 (4)C41—C40—C45119.2 (4)
C11—C10—H10119.7C41—C40—C39121.1 (3)
C9—C10—H10119.7C45—C40—C39119.6 (4)
C12—C11—C10119.1 (3)C40—C41—C42120.6 (4)
C12—C11—H11120.4C40—C41—H41119.7
C10—C11—H11120.4C42—C41—H41119.7
C11—C12—C13120.4 (4)C43—C42—C41119.5 (5)
C11—C12—H12119.8C43—C42—H42120.3
C13—C12—H12119.8C41—C42—H42120.3
C8—C13—C12120.7 (3)C44—C43—C42119.9 (4)
C8—C13—H13119.6C44—C43—H43120.1
C12—C13—H13119.6C42—C43—H43120.1
N5—C14—C15123.1 (4)C43—C44—C45121.1 (4)
N5—C14—H14118.4C43—C44—H44119.4
C15—C14—H14118.4C45—C44—H44119.4
C16—C15—C14118.7 (4)C44—C45—C40119.7 (4)
C16—C15—H15120.6C44—C45—H45120.1
C14—C15—H15120.6C40—C45—H45120.1
C17—C16—C15118.9 (4)N6—C46—C47122.6 (3)
C17—C16—H16120.6N6—C46—H46118.7
C15—C16—H16120.6C47—C46—H46118.7
C16—C17—C18119.7 (4)C46—C47—C48119.2 (4)
C16—C17—H17120.2C46—C47—H47120.4
C18—C17—H17120.2C48—C47—H47120.4
N5—C18—C17122.5 (3)C49—C48—C47118.4 (4)
N5—C18—H18118.7C49—C48—H48120.8
C17—C18—H18118.7C47—C48—H48120.8
O2—C19—N1125.4 (3)C48—C49—C50120.1 (4)
O2—C19—C20116.7 (3)C48—C49—H49119.9
N1—C19—C20117.8 (3)C50—C49—H49119.9
C21—C20—C25119.2 (3)N6—C50—C49122.2 (4)
C21—C20—C19122.1 (3)N6—C50—H50118.9
C25—C20—C19118.7 (3)C49—C50—H50118.9
N2—Cu1—O1—C1−2.7 (3)Cu1—O2—C19—N16.6 (4)
N5—Cu1—O1—C1−174.2 (3)Cu1—O2—C19—C20−173.0 (2)
N2—Cu1—O2—C19−5.8 (2)N2—N1—C19—O2−2.4 (4)
N5—Cu1—O2—C19165.1 (2)N2—N1—C19—C20177.2 (3)
N4—Cu2—O3—C262.2 (3)O2—C19—C20—C21144.6 (3)
N6—Cu2—O3—C26−177.1 (3)N1—C19—C20—C21−35.1 (5)
N4—Cu2—O4—C39−1.7 (2)O2—C19—C20—C25−33.0 (4)
N6—Cu2—O4—C39177.3 (2)N1—C19—C20—C25147.4 (3)
C19—N1—N2—C7174.3 (3)C25—C20—C21—C22−0.1 (5)
C19—N1—N2—Cu1−3.0 (3)C19—C20—C21—C22−177.6 (3)
O1—Cu1—N2—C73.3 (3)C20—C21—C22—C23−0.5 (6)
O2—Cu1—N2—C7−171.9 (3)C21—C22—C23—C24−0.2 (6)
N5—Cu1—N2—C7129.0 (6)C22—C23—C24—C251.4 (6)
O1—Cu1—N2—N1−179.8 (2)C23—C24—C25—C20−2.0 (5)
O2—Cu1—N2—N15.0 (2)C21—C20—C25—C241.3 (5)
N5—Cu1—N2—N1−54.1 (7)C19—C20—C25—C24178.9 (3)
C39—N3—N4—C32175.9 (3)Cu2—O3—C26—C31176.6 (2)
C39—N3—N4—Cu2−0.9 (3)Cu2—O3—C26—C27−3.3 (5)
O3—Cu2—N4—C320.3 (3)O3—C26—C27—C28179.2 (3)
O4—Cu2—N4—C32−174.9 (3)C31—C26—C27—C28−0.7 (5)
O3—Cu2—N4—N3176.7 (2)O3—C26—C27—C321.3 (5)
O4—Cu2—N4—N31.5 (2)C31—C26—C27—C32−178.6 (3)
O1—Cu1—N5—C18−154.3 (3)C26—C27—C28—C290.3 (5)
O2—Cu1—N5—C1821.5 (3)C32—C27—C28—C29178.3 (3)
N2—Cu1—N5—C1879.8 (7)C27—C28—C29—C30−0.1 (5)
O1—Cu1—N5—C1426.0 (3)C27—C28—C29—Br2179.8 (2)
O2—Cu1—N5—C14−158.1 (3)C28—C29—C30—C310.4 (6)
N2—Cu1—N5—C14−99.8 (6)Br2—C29—C30—C31−179.6 (3)
O3—Cu2—N6—C4627.0 (3)C29—C30—C31—C26−0.8 (6)
O4—Cu2—N6—C46−157.7 (3)O3—C26—C31—C30−178.9 (3)
O3—Cu2—N6—C50−156.0 (3)C27—C26—C31—C301.0 (5)
O4—Cu2—N6—C5019.3 (3)N3—N4—C32—C27−178.1 (3)
Cu1—O1—C1—C6−177.0 (2)Cu2—N4—C32—C27−1.9 (5)
Cu1—O1—C1—C22.2 (5)N3—N4—C32—C332.9 (4)
O1—C1—C2—C3176.7 (3)Cu2—N4—C32—C33179.1 (2)
C6—C1—C2—C3−4.0 (4)C28—C27—C32—N4−176.5 (3)
O1—C1—C2—C7−0.9 (5)C26—C27—C32—N41.3 (5)
C6—C1—C2—C7178.3 (3)C28—C27—C32—C332.5 (4)
C1—C2—C3—C42.2 (5)C26—C27—C32—C33−179.7 (3)
C7—C2—C3—C4179.9 (3)N4—C32—C33—C3463.1 (4)
C2—C3—C4—C50.7 (5)C27—C32—C33—C34−115.9 (4)
C2—C3—C4—Br1−178.6 (2)N4—C32—C33—C38−118.3 (4)
C3—C4—C5—C6−1.5 (5)C27—C32—C33—C3862.7 (4)
Br1—C4—C5—C6177.8 (3)C38—C33—C34—C35−1.5 (5)
C4—C5—C6—C1−0.6 (5)C32—C33—C34—C35177.0 (3)
O1—C1—C6—C5−177.3 (3)C33—C34—C35—C360.5 (6)
C2—C1—C6—C53.4 (5)C34—C35—C36—C370.3 (7)
N1—N2—C7—C2−179.8 (3)C35—C36—C37—C38−0.1 (7)
Cu1—N2—C7—C2−3.0 (4)C36—C37—C38—C33−1.0 (6)
N1—N2—C7—C8−0.6 (4)C34—C33—C38—C371.8 (5)
Cu1—N2—C7—C8176.2 (2)C32—C33—C38—C37−176.8 (3)
C3—C2—C7—N2−176.3 (3)Cu2—O4—C39—N31.9 (4)
C1—C2—C7—N21.3 (5)Cu2—O4—C39—C40179.3 (2)
C3—C2—C7—C84.5 (4)N4—N3—C39—O4−0.7 (5)
C1—C2—C7—C8−177.9 (3)N4—N3—C39—C40−178.1 (3)
N2—C7—C8—C975.3 (4)O4—C39—C40—C41167.8 (3)
C2—C7—C8—C9−105.5 (4)N3—C39—C40—C41−14.7 (5)
N2—C7—C8—C13−106.5 (4)O4—C39—C40—C45−12.7 (5)
C2—C7—C8—C1372.7 (4)N3—C39—C40—C45164.8 (3)
C13—C8—C9—C10−1.8 (5)C45—C40—C41—C42−0.9 (6)
C7—C8—C9—C10176.3 (3)C39—C40—C41—C42178.6 (4)
C8—C9—C10—C111.2 (6)C40—C41—C42—C43−0.2 (7)
C9—C10—C11—C120.2 (6)C41—C42—C43—C440.8 (7)
C10—C11—C12—C13−0.9 (6)C42—C43—C44—C45−0.3 (7)
C9—C8—C13—C121.2 (5)C43—C44—C45—C40−0.8 (7)
C7—C8—C13—C12−177.0 (3)C41—C40—C45—C441.4 (6)
C11—C12—C13—C80.2 (6)C39—C40—C45—C44−178.1 (3)
C18—N5—C14—C152.1 (5)C50—N6—C46—C47−1.6 (5)
Cu1—N5—C14—C15−178.3 (3)Cu2—N6—C46—C47175.5 (3)
N5—C14—C15—C16−0.8 (6)N6—C46—C47—C482.4 (6)
C14—C15—C16—C17−1.5 (6)C46—C47—C48—C49−0.9 (6)
C15—C16—C17—C182.6 (6)C47—C48—C49—C50−1.2 (6)
C14—N5—C18—C17−1.0 (6)C46—N6—C50—C49−0.6 (5)
Cu1—N5—C18—C17179.4 (3)Cu2—N6—C50—C49−177.6 (3)
C16—C17—C18—N5−1.3 (6)C48—C49—C50—N62.0 (6)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2158).

References

  • Bruker (2005). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zheng, C.-Z., Ji, C.-Y., Chang, X.-L. & Zhang, C.-H. (2009). Acta Cryst. E65, m965. [PMC free article] [PubMed]

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