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

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ISSN: 2056-9890

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

aCollege of Environmental and Chemical Engineering, Xi'an Polytechnic University, Xi'an, Shaanxi 710048, People's Republic of China, bSchool of Chemistry & Pharmaceutical Engineering, Sichuan University of Science & Engineering, Zigong, Sichuan 643000, People's Republic of China, and cLiaoning Key Laboratory of Applied Chemistry, Institute of Superfine Chemicals, Bohai University, Jinzhou,121000, People's Republic of China
*Correspondence e-mail: jichangyou789456@126.com

(Received 29 July 2009; accepted 31 July 2009; online 8 August 2009)

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[Zheng, C.-Z., Ji, C.-Y., Chang, X.-L. & Zhang, C.-H. (2009). Acta Cryst. E65, m965.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu(C20H13BrN2O2)(C5H5N)]

  • Mr = 535.87

  • Monoclinic, P 21 /c

  • 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[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.661, Tmax = 0.806

  • 22878 measured reflections

  • 7831 independent reflections

  • 5740 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 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[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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.

Related literature top

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

Experimental top

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 top

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).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] 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.
{N'-[(E)-(5-Bromo-2-oxidophenyl)(phenyl)methylene]benzohydrazidato}pyridinecopper(II) top
Crystal data top
[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 top
Bruker APEXII CCD area-detector
diffractometer
7831 independent reflections
Radiation source: fine-focus sealed tube5740 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ϕ and ω scansθmax = 25.1°, θmin = 1.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 2626
Tmin = 0.661, Tmax = 0.806k = 1212
22878 measured reflectionsl = 2318
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 1.09 w = 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
Crystal data top
[Cu(C20H13BrN2O2)(C5H5N)]V = 4424.9 (7) Å3
Mr = 535.87Z = 8
Monoclinic, P21/cMo Kα radiation
a = 22.655 (2) ŵ = 2.82 mm1
b = 10.6514 (10) ÅT = 295 K
c = 19.3388 (19) Å0.16 × 0.12 × 0.08 mm
β = 108.521 (2)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
7831 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
5740 reflections with I > 2σ(I)
Tmin = 0.661, Tmax = 0.806Rint = 0.029
22878 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.100H-atom parameters constrained
S = 1.09Δρmax = 0.46 e Å3
7831 reflectionsΔρmin = 0.57 e Å3
577 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
Cu10.448059 (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)
H110.60900.08400.42150.074*
C120.5731 (2)0.0446 (3)0.4724 (2)0.0658 (11)
H120.57110.00740.51020.079*
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)
H280.12660.17940.03940.052*
C290.07243 (16)0.1022 (3)0.13131 (18)0.0448 (8)
C300.03406 (17)0.0032 (3)0.16105 (19)0.0511 (9)
H300.01460.00210.21110.061*
C310.02517 (17)0.0870 (3)0.11555 (19)0.0523 (9)
H310.00040.15480.13570.063*
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)
H340.11430.23060.15110.065*
C350.1865 (2)0.3456 (4)0.1570 (2)0.0683 (12)
H350.17600.40740.18500.082*
C360.2384 (2)0.3594 (4)0.1361 (2)0.0724 (12)
H360.26320.43060.14980.087*
C370.2538 (2)0.2684 (4)0.0954 (2)0.0683 (12)
H370.28910.27760.08120.082*
C380.21764 (17)0.1639 (3)0.0751 (2)0.0530 (9)
H380.22900.10200.04790.064*
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)
H410.19390.06740.31630.076*
C420.2255 (2)0.0061 (5)0.4175 (2)0.0819 (14)
H420.24470.06650.44090.098*
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*
C460.03592 (16)0.3678 (3)0.0300 (2)0.0505 (9)
H460.04540.30830.00720.061*
C470.07398 (18)0.4696 (4)0.0230 (2)0.0573 (10)
H470.10950.47740.01730.069*
C480.0591 (2)0.5604 (4)0.0763 (2)0.0661 (11)
H480.08400.63120.07250.079*
C490.0072 (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) top
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, º) top
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—C12.7 (3)Cu1—O2—C19—N16.6 (4)
N5—Cu1—O1—C1174.2 (3)Cu1—O2—C19—C20173.0 (2)
N2—Cu1—O2—C195.8 (2)N2—N1—C19—O22.4 (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—C26177.1 (3)N1—C19—C20—C2135.1 (5)
N4—Cu2—O4—C391.7 (2)O2—C19—C20—C2533.0 (4)
N6—Cu2—O4—C39177.3 (2)N1—C19—C20—C25147.4 (3)
C19—N1—N2—C7174.3 (3)C25—C20—C21—C220.1 (5)
C19—N1—N2—Cu13.0 (3)C19—C20—C21—C22177.6 (3)
O1—Cu1—N2—C73.3 (3)C20—C21—C22—C230.5 (6)
O2—Cu1—N2—C7171.9 (3)C21—C22—C23—C240.2 (6)
N5—Cu1—N2—C7129.0 (6)C22—C23—C24—C251.4 (6)
O1—Cu1—N2—N1179.8 (2)C23—C24—C25—C202.0 (5)
O2—Cu1—N2—N15.0 (2)C21—C20—C25—C241.3 (5)
N5—Cu1—N2—N154.1 (7)C19—C20—C25—C24178.9 (3)
C39—N3—N4—C32175.9 (3)Cu2—O3—C26—C31176.6 (2)
C39—N3—N4—Cu20.9 (3)Cu2—O3—C26—C273.3 (5)
O3—Cu2—N4—C320.3 (3)O3—C26—C27—C28179.2 (3)
O4—Cu2—N4—C32174.9 (3)C31—C26—C27—C280.7 (5)
O3—Cu2—N4—N3176.7 (2)O3—C26—C27—C321.3 (5)
O4—Cu2—N4—N31.5 (2)C31—C26—C27—C32178.6 (3)
O1—Cu1—N5—C18154.3 (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—C300.1 (5)
O1—Cu1—N5—C1426.0 (3)C27—C28—C29—Br2179.8 (2)
O2—Cu1—N5—C14158.1 (3)C28—C29—C30—C310.4 (6)
N2—Cu1—N5—C1499.8 (6)Br2—C29—C30—C31179.6 (3)
O3—Cu2—N6—C4627.0 (3)C29—C30—C31—C260.8 (6)
O4—Cu2—N6—C46157.7 (3)O3—C26—C31—C30178.9 (3)
O3—Cu2—N6—C50156.0 (3)C27—C26—C31—C301.0 (5)
O4—Cu2—N6—C5019.3 (3)N3—N4—C32—C27178.1 (3)
Cu1—O1—C1—C6177.0 (2)Cu2—N4—C32—C271.9 (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—C34.0 (4)C28—C27—C32—N4176.5 (3)
O1—C1—C2—C70.9 (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—C33179.7 (3)
C7—C2—C3—C4179.9 (3)N4—C32—C33—C3463.1 (4)
C2—C3—C4—C50.7 (5)C27—C32—C33—C34115.9 (4)
C2—C3—C4—Br1178.6 (2)N4—C32—C33—C38118.3 (4)
C3—C4—C5—C61.5 (5)C27—C32—C33—C3862.7 (4)
Br1—C4—C5—C6177.8 (3)C38—C33—C34—C351.5 (5)
C4—C5—C6—C10.6 (5)C32—C33—C34—C35177.0 (3)
O1—C1—C6—C5177.3 (3)C33—C34—C35—C360.5 (6)
C2—C1—C6—C53.4 (5)C34—C35—C36—C370.3 (7)
N1—N2—C7—C2179.8 (3)C35—C36—C37—C380.1 (7)
Cu1—N2—C7—C23.0 (4)C36—C37—C38—C331.0 (6)
N1—N2—C7—C80.6 (4)C34—C33—C38—C371.8 (5)
Cu1—N2—C7—C8176.2 (2)C32—C33—C38—C37176.8 (3)
C3—C2—C7—N2176.3 (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—O40.7 (5)
C1—C2—C7—C8177.9 (3)N4—N3—C39—C40178.1 (3)
N2—C7—C8—C975.3 (4)O4—C39—C40—C41167.8 (3)
C2—C7—C8—C9105.5 (4)N3—C39—C40—C4114.7 (5)
N2—C7—C8—C13106.5 (4)O4—C39—C40—C4512.7 (5)
C2—C7—C8—C1372.7 (4)N3—C39—C40—C45164.8 (3)
C13—C8—C9—C101.8 (5)C45—C40—C41—C420.9 (6)
C7—C8—C9—C10176.3 (3)C39—C40—C41—C42178.6 (4)
C8—C9—C10—C111.2 (6)C40—C41—C42—C430.2 (7)
C9—C10—C11—C120.2 (6)C41—C42—C43—C440.8 (7)
C10—C11—C12—C130.9 (6)C42—C43—C44—C450.3 (7)
C9—C8—C13—C121.2 (5)C43—C44—C45—C400.8 (7)
C7—C8—C13—C12177.0 (3)C41—C40—C45—C441.4 (6)
C11—C12—C13—C80.2 (6)C39—C40—C45—C44178.1 (3)
C18—N5—C14—C152.1 (5)C50—N6—C46—C471.6 (5)
Cu1—N5—C14—C15178.3 (3)Cu2—N6—C46—C47175.5 (3)
N5—C14—C15—C160.8 (6)N6—C46—C47—C482.4 (6)
C14—C15—C16—C171.5 (6)C46—C47—C48—C490.9 (6)
C15—C16—C17—C182.6 (6)C47—C48—C49—C501.2 (6)
C14—N5—C18—C171.0 (6)C46—N6—C50—C490.6 (5)
Cu1—N5—C18—C17179.4 (3)Cu2—N6—C50—C49177.6 (3)
C16—C17—C18—N51.3 (6)C48—C49—C50—N62.0 (6)

Experimental details

Crystal data
Chemical formula[Cu(C20H13BrN2O2)(C5H5N)]
Mr535.87
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)22.655 (2), 10.6514 (10), 19.3388 (19)
β (°) 108.521 (2)
V3)4424.9 (7)
Z8
Radiation typeMo Kα
µ (mm1)2.82
Crystal size (mm)0.16 × 0.12 × 0.08
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.661, 0.806
No. of measured, independent and
observed [I > 2σ(I)] reflections
22878, 7831, 5740
Rint0.029
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.100, 1.09
No. of reflections7831
No. of parameters577
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.46, 0.57

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

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

References

First citationBruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationZheng, C.-Z., Ji, C.-Y., Chang, X.-L. & Zhang, C.-H. (2009). Acta Cryst. E65, m965.  Web of Science CSD CrossRef IUCr Journals

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