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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 11| November 2014| Pages m363-m364

Crystal structure of bis­­[2-(1H-benzimid­azol-2-yl)-4-bromo­phenolato-κ2N3,O]cobalt(II)

aKey Laboratory of Organosilicon Chemistry and Material Technology of the Ministry of Education, Hangzhou Normal University, Hangzhou 311121, People's Republic of China
*Correspondence e-mail: quzr@hznu.edu.cn

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 25 August 2014; accepted 3 October 2014; online 11 October 2014)

The asymmetric unit of the title CoII complex, [Co(C13H8BrN2O)2], contains two independent mol­ecules (A and B). In both mol­ecules, the CoII cation is N,O-chelated by two 2-(1H-benzimidazol-2-yl)-4-bromo­phenolate anions in a distorted tetra­hedral geometry. In mol­ecule A, both chelating rings display an envelope conformation, with the flap Co atom lying 0.614 (6) and 0.483 (6) Å from the mean planes of the remaining atoms. In mol­ecule B, both chelating rings are approximately planar, the maximum deviations being 0.039 (4) and 0.076 (3) Å. In the crystal, mol­ecules are linked by classical N—H⋯O hydrogen bonds and weak C—H⋯O and C—H⋯Br hydrogen bonds into a three-dimensional supra­molecular network. Extensive ππ stacking is observed between nearly parallel aromatic rings of adjacent mol­ecules with centroid–centroid distances in the range 3.407 (3)–3.850 (4) Å.

1. Related literature

For the crystal structures of related metal complexes with the ligand 2-(1H-benzoimidazol-2-yl)-4-bromo­phenolate, see: Li et al. (2002[Li, J., Zhang, F.-X. & Shi, Q.-Z. (2002). Chin. J. Inorg. Chem. 18, 643-646.]); Tong (2007[Tong, Y.-P. (2007). Chin. J. Struct. Chem. 26, 143-145.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • [Co(C13H8BrN2O)2]

  • Mr = 635.16

  • Monoclinic, P 21 /c

  • a = 22.4334 (16) Å

  • b = 8.3598 (6) Å

  • c = 30.0748 (16) Å

  • β = 125.323 (4)°

  • V = 4601.9 (5) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 4.25 mm−1

  • T = 293 K

  • 0.30 × 0.26 × 0.20 mm

2.2. Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.258, Tmax = 0.398

  • 29475 measured reflections

  • 10549 independent reflections

  • 5904 reflections with I > 2σ(I)

  • Rint = 0.053

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.166

  • S = 0.97

  • 10549 reflections

  • 631 parameters

  • H-atom parameters constrained

  • Δρmax = 0.71 e Å−3

  • Δρmin = −0.65 e Å−3

Table 1
Selected bond lengths (Å)

Co1—O2 1.912 (4)
Co1—O3 1.903 (4)
Co1—N2 1.975 (4)
Co1—N3 1.967 (4)
Co2—O1 1.930 (4)
Co2—O4 1.912 (4)
Co2—N6 1.961 (4)
Co2—N7 1.957 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1A⋯O1i 0.86 2.19 2.895 (5) 139
N4—H4A⋯O2ii 0.86 2.09 2.849 (5) 147
N5—H5A⋯O4iii 0.86 2.41 3.066 (5) 133
N8—H8A⋯O3iv 0.86 2.17 2.808 (5) 131
C4—H4⋯Br4i 0.93 2.88 3.703 (6) 149
C6—H6⋯Br1v 0.93 2.91 3.685 (6) 142
C35—H35⋯O2ii 0.93 2.54 3.394 (7) 153
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) -x+2, -y+1, -z+2; (iii) -x+1, -y+2, -z+2; (iv) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (v) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

The asymmetric unit of the title compound contains two crystallographically independent molecules and bond lengths and angles are in the normal range (Li et al., 2002; Tong, 2007). The Co(II) atom is coordinated by two N atoms and two O atoms to give a distorted tetrahedral geometry (Fig. 1). The benzimidazole and bromophenyl groups are nearly coplanar; the dihedral angle between them is 4.2 (3)°. The angles between the two ligand planes in each independent molecule are 71.66 (5)° and 63.66 (5)°, respectively. The crystal structure is stabilized by N–H···O hydrogen bonds linking molecules into a three-dimensional network structure (Fig. 2). The structure is further stabilized by π-π stacking interactions, the centroid-to-centroid separations are ranged from 3.407 (3) to 3.850 (4) Å.

Related literature top

For the crystal structures of related metal complexes with the ligand 2-(1H-benzimidazol-2-yl)-4-bromophenolate, see: Li et al. (2002); Tong (2007).

Experimental top

Synthesis of the ligand: The ligands were prepared by the reaction of the addition products of 2-hydroxy-5-bromobenzaldehyde (6 mmol 1.2 g) and NaHSO3 (6 mmol 0.65 g) were stirred at room temperature in ethanol (25 ml) and a precipitate is formed after 4 h reaction, then, o-phenylenediamine (6 mmol, 0.65 g) and 25 ml DMF were added to this mixture. After 2 h reflux the solution was poured into 10-times water. The benzimidazole compound was filtered, dried and crystallized from ethanol.

Synthesis of the complex [Co(C26H16N4O2Br2)]2: 2-(1H-benzimidazol-2-yl)-4-bromophenol (0.2 mmol, 58 mg) was dissolved in DMF (6 ml) and CoCl2.6H2O (0.1 mmol 24 mg) was dissolved in H2O (6 ml), and the mixture poured into a 25 ml dicting kettle, then maintaining 393 K for 3 d, allowed to reach room temperate, and red block-shaped crystals suitable for X-ray diffraction were obtained.

Refinement top

H atoms were placed in calculated positions with C—H = 0.97-0.93 Å and N—H = 0.86 Å, and refined in riding mode, Uiso(H) = 1.2Ueq(C,N).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
Fig.1. A view of the asymmetric unit of the title compound with atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level and all H atoms have been omitted for clarity.

Fig.2. Packing diagram of the title compound viewed along the c axis. Hydrogen bonds are shown as dashed lines.
Bis[2-(1H-benzimidazol-2-yl)-4-bromophenolato-κ2N3,O]cobalt(II) top
Crystal data top
[Co(C13H8BrN2O)2]F(000) = 2503
Mr = 635.16Dx = 1.834 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 22.4334 (16) ÅCell parameters from 29475 reflections
b = 8.3598 (6) Åθ = 1.1–27.5°
c = 30.0748 (16) ŵ = 4.25 mm1
β = 125.323 (4)°T = 293 K
V = 4601.9 (5) Å3Block, red
Z = 80.30 × 0.26 × 0.20 mm
Data collection top
Bruker APEXII CCD
diffractometer
10549 independent reflections
Radiation source: fine-focus sealed tube5904 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
ϕ and ω scansθmax = 27.5°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 2922
Tmin = 0.258, Tmax = 0.398k = 1010
29475 measured reflectionsl = 3639
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0908P)2]
where P = (Fo2 + 2Fc2)/3
10549 reflections(Δ/σ)max = 0.001
631 parametersΔρmax = 0.71 e Å3
0 restraintsΔρmin = 0.65 e Å3
Crystal data top
[Co(C13H8BrN2O)2]V = 4601.9 (5) Å3
Mr = 635.16Z = 8
Monoclinic, P21/cMo Kα radiation
a = 22.4334 (16) ŵ = 4.25 mm1
b = 8.3598 (6) ÅT = 293 K
c = 30.0748 (16) Å0.30 × 0.26 × 0.20 mm
β = 125.323 (4)°
Data collection top
Bruker APEXII CCD
diffractometer
10549 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
5904 reflections with I > 2σ(I)
Tmin = 0.258, Tmax = 0.398Rint = 0.053
29475 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.166H-atom parameters constrained
S = 0.97Δρmax = 0.71 e Å3
10549 reflectionsΔρmin = 0.65 e Å3
631 parameters
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
Br10.58763 (3)0.94519 (8)0.67243 (2)0.04708 (19)
Br20.96705 (4)0.01562 (9)1.09681 (2)0.0546 (2)
Co10.90832 (4)0.46833 (10)0.87113 (3)0.0345 (2)
O20.85783 (19)0.6568 (5)0.86818 (12)0.0383 (10)
O30.86633 (19)0.2923 (5)0.88397 (12)0.0439 (10)
N20.8868 (2)0.5101 (5)0.79854 (15)0.0278 (10)
N10.8152 (2)0.5734 (5)0.71102 (15)0.0298 (10)
H1A0.77950.61410.68090.036*
N31.0079 (2)0.4220 (5)0.93502 (15)0.0321 (10)
N41.0909 (2)0.3509 (5)1.02030 (15)0.0312 (10)
H4A1.11000.30931.05200.037*
C410.9158 (3)0.4410 (7)0.77260 (19)0.0354 (13)
C281.0753 (3)0.4820 (7)0.9510 (2)0.0337 (13)
C360.9396 (3)0.0799 (7)1.0302 (2)0.0380 (14)
C400.8271 (3)0.5913 (6)0.76042 (17)0.0260 (11)
C271.0192 (3)0.3386 (7)0.97719 (17)0.0298 (12)
C460.8705 (3)0.4784 (7)0.7173 (2)0.0301 (12)
C450.8855 (3)0.4264 (8)0.6813 (2)0.0437 (15)
H450.85500.45120.64440.052*
C480.7168 (3)0.7559 (7)0.72527 (18)0.0340 (13)
H480.70500.74190.69040.041*
C331.1276 (3)0.4405 (7)1.0050 (2)0.0365 (13)
C490.6728 (3)0.8449 (7)0.73248 (19)0.0335 (13)
C350.9864 (3)0.1691 (7)1.02718 (18)0.0315 (12)
H351.03410.18071.05800.038*
C340.9655 (3)0.2465 (7)0.97832 (17)0.0303 (12)
C430.9927 (3)0.2955 (8)0.7576 (2)0.0488 (16)
H431.03360.23230.77020.059*
C440.9470 (3)0.3370 (9)0.7022 (2)0.0534 (18)
H440.95910.30230.67900.064*
C311.2178 (3)0.5794 (9)1.0040 (3)0.0572 (18)
H311.26550.61611.02150.069*
C500.6885 (3)0.8666 (7)0.7841 (2)0.0408 (14)
H500.65690.92420.78860.049*
C470.7801 (2)0.6842 (6)0.76986 (17)0.0254 (11)
C420.9773 (3)0.3479 (8)0.7936 (2)0.0468 (16)
H421.00710.32130.83040.056*
C370.8683 (3)0.0559 (7)0.9848 (2)0.0454 (15)
H370.83600.00780.98690.054*
C510.7506 (3)0.8027 (7)0.82781 (19)0.0388 (14)
H510.76170.82040.86240.047*
C321.2000 (3)0.4847 (8)1.0325 (3)0.0505 (17)
H321.23490.45261.06820.061*
C390.8932 (3)0.2255 (7)0.93201 (18)0.0326 (13)
C520.7979 (3)0.7121 (6)0.82274 (18)0.0292 (12)
C291.0957 (3)0.5776 (8)0.9235 (2)0.0474 (16)
H291.06130.61010.88770.057*
C301.1663 (3)0.6213 (10)0.9498 (3)0.063 (2)
H301.18080.68050.93140.076*
C380.8472 (3)0.1294 (8)0.9369 (2)0.0451 (15)
H380.79970.11370.90630.054*
Br30.33496 (4)1.05417 (12)1.10266 (3)0.0769 (3)
Br40.39831 (4)0.96643 (12)0.64170 (3)0.0711 (3)
Co20.37925 (4)0.92802 (10)0.87904 (3)0.0363 (2)
O10.3195 (2)1.0374 (5)0.89651 (14)0.0451 (11)
O40.4319 (2)1.0277 (5)0.85430 (14)0.0430 (10)
N60.4425 (2)0.8299 (6)0.95131 (15)0.0340 (11)
N50.4949 (2)0.7840 (5)1.03884 (15)0.0323 (10)
H5A0.50320.78761.07050.039*
N70.3160 (2)0.8034 (6)0.81237 (15)0.0339 (11)
N80.2534 (2)0.7465 (6)0.72462 (15)0.0356 (11)
H8A0.24000.74750.69140.043*
C130.3259 (3)1.0325 (7)0.9430 (2)0.0382 (14)
C210.3638 (3)0.9139 (7)0.76286 (19)0.0359 (13)
C140.3128 (3)0.8257 (7)0.76724 (18)0.0324 (13)
C80.3808 (3)0.9497 (7)0.9903 (2)0.0355 (13)
C30.5332 (3)0.6743 (7)0.9445 (2)0.0425 (15)
H30.51160.69530.90780.051*
C190.1575 (3)0.5672 (7)0.7178 (2)0.0435 (15)
H190.13120.54320.68090.052*
C60.5994 (3)0.6084 (7)1.0561 (2)0.0409 (15)
H60.62130.58611.09280.049*
C20.5037 (3)0.7354 (7)0.97079 (18)0.0314 (12)
C90.3807 (3)0.9555 (7)1.0370 (2)0.0393 (14)
H90.41660.90051.06820.047*
C40.5948 (3)0.5823 (8)0.9741 (2)0.0478 (16)
H40.61560.54060.95730.057*
C150.2582 (3)0.7042 (7)0.79894 (19)0.0344 (13)
C260.4212 (3)1.0058 (8)0.8068 (2)0.0404 (15)
C10.4374 (3)0.8591 (7)0.99257 (18)0.0319 (12)
C100.3293 (3)1.0395 (8)1.0377 (2)0.0455 (16)
C170.1765 (3)0.5397 (7)0.8052 (3)0.0471 (16)
H170.16110.49470.82530.057*
C200.2184 (3)0.6648 (6)0.7434 (2)0.0303 (12)
C240.4628 (3)1.0748 (9)0.7502 (3)0.0521 (17)
H240.49511.12930.74570.062*
C50.6266 (3)0.5506 (8)1.0284 (2)0.0478 (16)
H50.66840.48731.04710.057*
C70.5373 (3)0.7018 (7)1.02606 (18)0.0307 (12)
C250.4695 (3)1.0851 (8)0.7981 (2)0.0454 (16)
H250.50721.14650.82610.054*
C160.2367 (3)0.6371 (7)0.8302 (2)0.0381 (13)
H160.26280.65820.86730.046*
C220.3593 (3)0.9059 (9)0.7142 (2)0.0464 (16)
H220.32190.84630.68530.056*
C120.2744 (3)1.1173 (8)0.9458 (2)0.0425 (14)
H120.23741.17150.91500.051*
C230.4072 (3)0.9819 (8)0.7081 (2)0.0457 (16)
C110.2759 (3)1.1239 (8)0.9918 (2)0.0445 (15)
H110.24161.18440.99250.053*
C180.1387 (3)0.5089 (8)0.7500 (3)0.0480 (16)
H180.09760.44370.73400.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0315 (3)0.0561 (5)0.0418 (3)0.0132 (3)0.0143 (3)0.0101 (3)
Br20.0679 (5)0.0629 (5)0.0378 (3)0.0107 (4)0.0334 (3)0.0182 (3)
Co10.0303 (4)0.0474 (5)0.0209 (3)0.0058 (4)0.0121 (3)0.0074 (3)
O20.036 (2)0.052 (3)0.0194 (16)0.0137 (19)0.0118 (15)0.0036 (16)
O30.034 (2)0.063 (3)0.0200 (16)0.001 (2)0.0066 (15)0.0088 (17)
N20.027 (2)0.031 (3)0.0247 (19)0.010 (2)0.0150 (18)0.0085 (18)
N10.025 (2)0.039 (3)0.0226 (19)0.010 (2)0.0126 (17)0.0071 (18)
N30.032 (2)0.038 (3)0.0239 (19)0.002 (2)0.0144 (18)0.0046 (19)
N40.026 (2)0.039 (3)0.0194 (18)0.002 (2)0.0085 (18)0.0029 (18)
C410.029 (3)0.055 (4)0.026 (2)0.006 (3)0.017 (2)0.002 (2)
C280.033 (3)0.036 (3)0.033 (3)0.002 (3)0.019 (2)0.002 (2)
C360.047 (3)0.042 (4)0.027 (2)0.005 (3)0.023 (3)0.006 (2)
C400.024 (3)0.027 (3)0.022 (2)0.005 (2)0.010 (2)0.004 (2)
C270.029 (3)0.035 (3)0.017 (2)0.008 (2)0.009 (2)0.002 (2)
C460.023 (3)0.031 (3)0.034 (3)0.005 (2)0.015 (2)0.002 (2)
C450.045 (3)0.061 (5)0.035 (3)0.005 (3)0.029 (3)0.007 (3)
C480.028 (3)0.049 (4)0.022 (2)0.002 (3)0.012 (2)0.001 (2)
C330.031 (3)0.042 (4)0.032 (3)0.009 (3)0.016 (2)0.003 (2)
C490.024 (3)0.043 (4)0.030 (2)0.003 (3)0.013 (2)0.002 (2)
C350.030 (3)0.041 (4)0.021 (2)0.010 (3)0.013 (2)0.002 (2)
C340.030 (3)0.037 (3)0.021 (2)0.004 (2)0.013 (2)0.000 (2)
C430.047 (4)0.050 (4)0.060 (4)0.023 (3)0.036 (3)0.011 (3)
C440.053 (4)0.072 (5)0.055 (4)0.002 (4)0.043 (3)0.010 (3)
C310.034 (3)0.068 (5)0.067 (4)0.003 (3)0.028 (3)0.003 (4)
C500.042 (3)0.043 (4)0.044 (3)0.001 (3)0.029 (3)0.007 (3)
C470.022 (2)0.029 (3)0.024 (2)0.003 (2)0.013 (2)0.003 (2)
C420.033 (3)0.071 (5)0.043 (3)0.006 (3)0.026 (3)0.008 (3)
C370.041 (3)0.049 (4)0.041 (3)0.006 (3)0.021 (3)0.007 (3)
C510.038 (3)0.055 (4)0.024 (2)0.005 (3)0.018 (2)0.004 (2)
C320.031 (3)0.069 (5)0.045 (3)0.005 (3)0.018 (3)0.004 (3)
C390.033 (3)0.039 (4)0.022 (2)0.002 (3)0.013 (2)0.005 (2)
C520.024 (3)0.031 (3)0.026 (2)0.001 (2)0.011 (2)0.002 (2)
C290.049 (4)0.048 (4)0.045 (3)0.006 (3)0.027 (3)0.012 (3)
C300.041 (4)0.097 (6)0.063 (4)0.004 (4)0.037 (3)0.020 (4)
C380.033 (3)0.054 (4)0.035 (3)0.008 (3)0.011 (3)0.006 (3)
Br30.0629 (5)0.1340 (9)0.0506 (4)0.0121 (5)0.0425 (4)0.0018 (4)
Br40.0482 (4)0.1339 (8)0.0419 (3)0.0164 (4)0.0321 (3)0.0144 (4)
Co20.0329 (4)0.0487 (5)0.0187 (3)0.0001 (4)0.0099 (3)0.0015 (3)
O10.036 (2)0.066 (3)0.0241 (17)0.003 (2)0.0122 (16)0.0008 (18)
O40.035 (2)0.061 (3)0.0247 (17)0.005 (2)0.0129 (16)0.0056 (18)
N60.030 (2)0.047 (3)0.0204 (19)0.006 (2)0.0116 (18)0.0050 (19)
N50.031 (2)0.038 (3)0.0220 (19)0.002 (2)0.0120 (18)0.0006 (18)
N70.027 (2)0.046 (3)0.0221 (19)0.012 (2)0.0103 (18)0.0069 (19)
N80.029 (2)0.054 (3)0.0173 (18)0.005 (2)0.0098 (18)0.004 (2)
C130.030 (3)0.049 (4)0.029 (3)0.012 (3)0.014 (2)0.010 (2)
C210.027 (3)0.053 (4)0.025 (2)0.005 (3)0.014 (2)0.001 (2)
C140.029 (3)0.046 (4)0.022 (2)0.013 (3)0.014 (2)0.003 (2)
C80.027 (3)0.047 (4)0.029 (2)0.014 (3)0.014 (2)0.011 (2)
C30.044 (3)0.051 (4)0.027 (3)0.003 (3)0.017 (3)0.005 (3)
C190.032 (3)0.035 (4)0.050 (3)0.001 (3)0.016 (3)0.007 (3)
C60.041 (3)0.050 (4)0.024 (2)0.001 (3)0.014 (2)0.007 (2)
C20.028 (3)0.035 (3)0.022 (2)0.005 (3)0.009 (2)0.000 (2)
C90.037 (3)0.047 (4)0.031 (3)0.013 (3)0.019 (2)0.006 (2)
C40.045 (4)0.064 (5)0.038 (3)0.007 (3)0.026 (3)0.003 (3)
C150.034 (3)0.036 (4)0.031 (3)0.019 (3)0.018 (2)0.010 (2)
C260.031 (3)0.061 (4)0.025 (2)0.006 (3)0.014 (2)0.002 (3)
C10.028 (3)0.038 (4)0.025 (2)0.010 (3)0.012 (2)0.006 (2)
C100.036 (3)0.061 (5)0.042 (3)0.013 (3)0.024 (3)0.010 (3)
C170.047 (4)0.031 (4)0.072 (4)0.005 (3)0.039 (3)0.012 (3)
C200.027 (3)0.021 (3)0.038 (3)0.001 (2)0.016 (2)0.003 (2)
C240.037 (3)0.072 (5)0.057 (4)0.003 (3)0.032 (3)0.009 (3)
C50.037 (3)0.055 (5)0.044 (3)0.009 (3)0.020 (3)0.005 (3)
C70.028 (3)0.036 (3)0.026 (2)0.009 (3)0.015 (2)0.004 (2)
C250.032 (3)0.058 (4)0.038 (3)0.017 (3)0.015 (3)0.005 (3)
C160.042 (3)0.031 (3)0.040 (3)0.006 (3)0.023 (3)0.006 (3)
C220.035 (3)0.073 (5)0.029 (3)0.012 (3)0.018 (3)0.007 (3)
C120.034 (3)0.044 (4)0.041 (3)0.009 (3)0.017 (3)0.002 (3)
C230.038 (3)0.068 (5)0.038 (3)0.009 (3)0.026 (3)0.008 (3)
C110.039 (3)0.047 (4)0.051 (3)0.005 (3)0.028 (3)0.005 (3)
C180.032 (3)0.038 (4)0.068 (4)0.004 (3)0.025 (3)0.000 (3)
Geometric parameters (Å, º) top
Br1—C491.904 (5)Br3—C101.889 (6)
Br2—C361.898 (5)Br4—C231.893 (6)
Co1—O21.912 (4)Co2—O11.930 (4)
Co1—O31.903 (4)Co2—O41.912 (4)
Co1—N21.975 (4)Co2—N61.961 (4)
Co1—N31.967 (4)Co2—N71.957 (4)
O2—C521.328 (5)O1—C131.322 (6)
O3—C391.325 (5)O4—C261.316 (6)
N2—C401.339 (6)N6—C11.332 (6)
N2—C411.399 (6)N6—C21.388 (7)
N1—C401.358 (6)N5—C11.385 (6)
N1—C461.390 (6)N5—C71.396 (7)
N1—H1A0.8600N5—H5A0.8600
N3—C271.336 (6)N7—C141.330 (6)
N3—C281.389 (7)N7—C151.388 (7)
N4—C271.366 (6)N8—C141.372 (6)
N4—C331.375 (7)N8—C201.384 (7)
N4—H4A0.8600N8—H8A0.8600
C41—C421.378 (8)C13—C121.400 (8)
C41—C461.392 (7)C13—C81.412 (8)
C28—C331.388 (7)C21—C221.408 (7)
C28—C291.406 (8)C21—C261.424 (8)
C36—C351.334 (8)C21—C141.430 (8)
C36—C371.391 (8)C8—C91.406 (7)
C40—C471.462 (7)C8—C11.447 (8)
C27—C341.448 (7)C3—C41.369 (8)
C46—C451.377 (7)C3—C21.389 (7)
C45—C441.362 (8)C3—H30.9300
C45—H450.9300C19—C181.351 (9)
C48—C491.350 (7)C19—C201.382 (8)
C48—C471.405 (7)C19—H190.9300
C48—H480.9300C6—C51.376 (8)
C33—C321.381 (8)C6—C71.381 (7)
C49—C501.391 (7)C6—H60.9300
C35—C341.414 (6)C2—C71.401 (6)
C35—H350.9300C9—C101.359 (8)
C34—C391.410 (7)C9—H90.9300
C43—C421.385 (8)C4—C51.378 (8)
C43—C441.403 (8)C4—H40.9300
C43—H430.9300C15—C161.399 (7)
C44—H440.9300C15—C201.403 (7)
C31—C321.386 (9)C26—C251.420 (8)
C31—C301.391 (9)C10—C111.387 (8)
C31—H310.9300C17—C161.370 (8)
C50—C511.354 (7)C17—C181.385 (9)
C50—H500.9300C17—H170.9300
C47—C521.417 (6)C24—C251.361 (8)
C42—H420.9300C24—C231.391 (9)
C37—C381.375 (7)C24—H240.9300
C37—H370.9300C5—H50.9300
C51—C521.383 (7)C25—H250.9300
C51—H510.9300C16—H160.9300
C32—H320.9300C22—C231.351 (9)
C39—C381.382 (8)C22—H220.9300
C29—C301.347 (8)C12—C111.364 (8)
C29—H290.9300C12—H120.9300
C30—H300.9300C11—H110.9300
C38—H380.9300C18—H180.9300
O3—Co1—O2107.28 (18)O4—Co2—O1125.57 (19)
O3—Co1—N393.74 (17)O4—Co2—N794.49 (17)
O2—Co1—N3121.01 (17)O1—Co2—N7108.97 (17)
O3—Co1—N2121.83 (17)O4—Co2—N6113.60 (17)
O2—Co1—N292.47 (15)O1—Co2—N693.86 (17)
N3—Co1—N2121.93 (17)N7—Co2—N6123.0 (2)
C52—O2—Co1123.7 (3)C13—O1—Co2127.3 (4)
C39—O3—Co1125.5 (3)C26—O4—Co2126.5 (4)
C40—N2—C41106.9 (4)C1—N6—C2107.9 (4)
C40—N2—Co1121.4 (3)C1—N6—Co2124.0 (4)
C41—N2—Co1130.4 (3)C2—N6—Co2127.7 (3)
C40—N1—C46108.6 (4)C1—N5—C7109.5 (4)
C40—N1—H1A125.7C1—N5—H5A125.3
C46—N1—H1A125.7C7—N5—H5A125.3
C27—N3—C28106.7 (4)C14—N7—C15107.2 (4)
C27—N3—Co1121.0 (4)C14—N7—Co2123.4 (4)
C28—N3—Co1131.4 (3)C15—N7—Co2128.2 (3)
C27—N4—C33109.1 (4)C14—N8—C20109.3 (4)
C27—N4—H4A125.4C14—N8—H8A125.4
C33—N4—H4A125.4C20—N8—H8A125.4
C42—C41—C46121.4 (5)O1—C13—C12117.4 (5)
C42—C41—N2130.0 (5)O1—C13—C8125.4 (5)
C46—C41—N2108.6 (5)C12—C13—C8117.2 (5)
C33—C28—N3109.2 (5)C22—C21—C26118.3 (5)
C33—C28—C29119.2 (5)C22—C21—C14119.4 (5)
N3—C28—C29131.5 (5)C26—C21—C14122.3 (5)
C35—C36—C37121.1 (5)N7—C14—N8109.7 (5)
C35—C36—Br2121.3 (4)N7—C14—C21126.3 (5)
C37—C36—Br2117.6 (4)N8—C14—C21124.0 (4)
N2—C40—N1110.3 (4)C9—C8—C13119.0 (5)
N2—C40—C47125.4 (4)C9—C8—C1118.7 (5)
N1—C40—C47124.3 (4)C13—C8—C1122.3 (5)
N3—C27—N4109.6 (5)C4—C3—C2118.1 (5)
N3—C27—C34126.6 (4)C4—C3—H3121.0
N4—C27—C34123.9 (4)C2—C3—H3121.0
C45—C46—N1132.6 (5)C18—C19—C20115.6 (6)
C45—C46—C41121.7 (5)C18—C19—H19122.2
N1—C46—C41105.7 (4)C20—C19—H19122.2
C44—C45—C46116.9 (5)C5—C6—C7115.8 (5)
C44—C45—H45121.5C5—C6—H6122.1
C46—C45—H45121.5C7—C6—H6122.1
C49—C48—C47120.8 (4)N6—C2—C3130.6 (4)
C49—C48—H48119.6N6—C2—C7109.7 (4)
C47—C48—H48119.6C3—C2—C7119.7 (5)
N4—C33—C32132.0 (5)C10—C9—C8121.5 (6)
N4—C33—C28105.2 (5)C10—C9—H9119.2
C32—C33—C28122.7 (6)C8—C9—H9119.2
C48—C49—C50120.9 (5)C3—C4—C5121.0 (6)
C48—C49—Br1121.1 (4)C3—C4—H4119.5
C50—C49—Br1118.0 (4)C5—C4—H4119.5
C36—C35—C34121.7 (5)N7—C15—C16132.2 (5)
C36—C35—H35119.2N7—C15—C20109.4 (5)
C34—C35—H35119.2C16—C15—C20118.4 (5)
C39—C34—C35118.1 (5)O4—C26—C25117.2 (5)
C39—C34—C27122.7 (4)O4—C26—C21125.6 (5)
C35—C34—C27119.1 (4)C25—C26—C21117.2 (5)
C42—C43—C44120.6 (6)N6—C1—N5108.8 (5)
C42—C43—H43119.7N6—C1—C8126.7 (5)
C44—C43—H43119.7N5—C1—C8124.5 (4)
C45—C44—C43122.3 (5)C9—C10—C11120.1 (5)
C45—C44—H44118.9C9—C10—Br3119.9 (5)
C43—C44—H44118.9C11—C10—Br3119.8 (5)
C32—C31—C30121.9 (6)C16—C17—C18119.6 (6)
C32—C31—H31119.1C16—C17—H17120.2
C30—C31—H31119.1C18—C17—H17120.2
C51—C50—C49119.2 (5)C19—C20—N8132.4 (5)
C51—C50—H50120.4C19—C20—C15123.1 (5)
C49—C50—H50120.4N8—C20—C15104.5 (4)
C48—C47—C52118.3 (4)C25—C24—C23119.4 (6)
C48—C47—C40119.1 (4)C25—C24—H24120.3
C52—C47—C40122.5 (4)C23—C24—H24120.3
C41—C42—C43117.1 (5)C6—C5—C4123.0 (6)
C41—C42—H42121.5C6—C5—H5118.5
C43—C42—H42121.5C4—C5—H5118.5
C38—C37—C36118.0 (6)C6—C7—N5133.4 (4)
C38—C37—H37121.0C6—C7—C2122.5 (5)
C36—C37—H37121.0N5—C7—C2104.1 (4)
C50—C51—C52122.2 (5)C24—C25—C26122.5 (6)
C50—C51—H51118.9C24—C25—H25118.7
C52—C51—H51118.9C26—C25—H25118.7
C33—C32—C31116.2 (6)C17—C16—C15119.0 (5)
C33—C32—H32121.9C17—C16—H16120.5
C31—C32—H32121.9C15—C16—H16120.5
O3—C39—C38117.6 (5)C23—C22—C21122.3 (6)
O3—C39—C34124.3 (5)C23—C22—H22118.8
C38—C39—C34118.1 (4)C21—C22—H22118.8
O2—C52—C51117.5 (4)C11—C12—C13123.0 (5)
O2—C52—C47124.0 (5)C11—C12—H12118.5
C51—C52—C47118.5 (4)C13—C12—H12118.5
C30—C29—C28118.7 (6)C22—C23—C24120.3 (6)
C30—C29—H29120.7C22—C23—Br4120.3 (5)
C28—C29—H29120.7C24—C23—Br4119.4 (5)
C29—C30—C31121.2 (6)C12—C11—C10119.1 (6)
C29—C30—H30119.4C12—C11—H11120.4
C31—C30—H30119.4C10—C11—H11120.4
C37—C38—C39123.0 (5)C19—C18—C17124.3 (6)
C37—C38—H38118.5C19—C18—H18117.8
C39—C38—H38118.5C17—C18—H18117.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.862.192.895 (5)139
N4—H4A···O2ii0.862.092.849 (5)147
N5—H5A···O4iii0.862.413.066 (5)133
N8—H8A···O3iv0.862.172.808 (5)131
C4—H4···Br4i0.932.883.703 (6)149
C6—H6···Br1v0.932.913.685 (6)142
C35—H35···O2ii0.932.543.394 (7)153
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x+2, y+1, z+2; (iii) x+1, y+2, z+2; (iv) x+1, y+1/2, z+3/2; (v) x, y+3/2, z+1/2.
Selected bond lengths (Å) top
Co1—O21.912 (4)Co2—O11.930 (4)
Co1—O31.903 (4)Co2—O41.912 (4)
Co1—N21.975 (4)Co2—N61.961 (4)
Co1—N31.967 (4)Co2—N71.957 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.862.192.895 (5)139
N4—H4A···O2ii0.862.092.849 (5)147
N5—H5A···O4iii0.862.413.066 (5)133
N8—H8A···O3iv0.862.172.808 (5)131
C4—H4···Br4i0.932.883.703 (6)149
C6—H6···Br1v0.932.913.685 (6)142
C35—H35···O2ii0.932.543.394 (7)153
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x+2, y+1, z+2; (iii) x+1, y+2, z+2; (iv) x+1, y+1/2, z+3/2; (v) x, y+3/2, z+1/2.
 

Acknowledgements

This work was supported by a start-up grant from Hangzhou Normal University, China.

References

First citationBruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLi, J., Zhang, F.-X. & Shi, Q.-Z. (2002). Chin. J. Inorg. Chem. 18, 643–646.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTong, Y.-P. (2007). Chin. J. Struct. Chem. 26, 143–145.  CAS Google Scholar

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Volume 70| Part 11| November 2014| Pages m363-m364
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