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Acta Cryst. (2007). E63, m3037    [ doi:10.1107/S1600536807053044 ]

Bis[2,4-dibromo-6-(1-naphthyliminomethyl)phenolato-[kappa]2N,O]bis(N,N'-dimethylformamide-[kappa]O)cobalt(II)

Z. Liu, L. X. Jin, J. H. Xia, E. X. Liu and G. Z. Li

Abstract top

In the title compound, [Co(C17H10Br2NO)2(C3H7NO)2], the cobalt(II) cation is coordinated by two N and two O atoms from two different Schiff base ligands, and two O atoms from dimethylformamide molecules, forming a slightly distorted octahedral geometry. In the crystal structure, C-H...Br hydrogen bonds link the molecules in rows.

Comment top

Schiff bases play an important role in inorganic chemistry as they easily form stable complexes with most transition metal ions (Mostafa & Haifaa, 2007, Musie et al., 2003; Patel et al., 2006). Schiff bases of isatin were reported to possess antibacterial, antifungal, antiviral, anti-HIV, antiprotozoal, and anthelmintic activities (Erçağ et al., 2006). We report herein the synthesis and crystal structure of the ternary mixed ligand complex resulting from the condensation of 1-naphthylamine-3,5-bibromo-2-hydroxy- benzaldehyde and Co(NO3)2.

As shown in Fig. 1, the CoII cation lies on a twofold axis and is coordinated by two N and two O atoms from the Schiff base and two O atoms from N,N'-dimethyl-formamide, in a slightly distorted octahedral geometry. In the crystal weak, non-classical C—H···Br hydrogen bonds link the molecules in rows (Fig 2).

Related literature top

Schiff bases of isatin have been reported to possess antibacterial, antifungal, antiviral, anti-HIV, antiprotozoal, and anthelmintic activities (Erçağ et al., 2006).

For related literature, see: El-Behery & El-Twigry (2007); Mostafa & Haifaa (2007); Musie et al. (2003); Patel et al. (2006).

Experimental top

1-naphthylamine (0.286 g, 2 mmol) and 3,5-bibromo-2-hydroxy-benzaldehyde (0.560 g, 2 mmol) were mixed in ethanol and and stirred for 30 min at room temperature to yield the Schiff base 2,4-dibromo-6-((naphthalen-1-ylimino) methyl)phenol. A mixture of schiff base (0.201 g, 0.5 mmol), CoNO3·6H2O2 (0.145 g, 0.5 mmol) and 6 drops of triethylamine in 5 ml e thanol and 5 ml DMF were sealed in a 30 ml Teflon-lined stainless steel vessel, which was heated at 333 K for 7 days under autogenous pressure. On cooling to room temperature blue crystals of the title compound were produced (yield: 53%, based on Co).

Refinement top

All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.93 − 0.96 Å, Uiso = 1.2 or 1.5Ueq (C).

Computing details top

Data collection: SAINT (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures top
[Figure 1] Fig. 1. A view of (I), showing 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. Crystal packing of (I) with H-bonds drawn as dashed lines.
Bis[2,4-dibromo-6-(1-naphthyliminomethyl)phenolato-κ2N,O]\ bis(N,N'-dimethylformamide-κO)cobalt(II) top
Crystal data top
[Co(C17H10Br2NO)2(C3H7NO)2]F000 = 2004
Mr = 1013.28Dx = 1.661 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3177 reflections
a = 12.2884 (15) Åθ = 2.6–25.1º
b = 17.069 (2) ŵ = 4.41 mm−1
c = 19.373 (2) ÅT = 298 (2) K
β = 94.310 (2)ºBlock, red
V = 4052.0 (9) Å30.21 × 0.15 × 0.14 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		7147 independent reflections
Radiation source: fine-focus sealed tube2955 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.090
T = 298(2) Kθmax = 25.0º
φ and ω scansθmin = 1.6º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −14→14
Tmin = 0.458, Tmax = 0.577k = −20→12
20849 measured reflectionsl = −23→22
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.123  w = 1/[σ2(Fo2) + (0.0363P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
7147 reflectionsΔρmax = 0.77 e Å−3
478 parametersΔρmin = −0.75 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Co(C17H10Br2NO)2(C3H7NO)2]V = 4052.0 (9) Å3
Mr = 1013.28Z = 4
Monoclinic, P21/nMo Kα
a = 12.2884 (15) ŵ = 4.41 mm−1
b = 17.069 (2) ÅT = 298 (2) K
c = 19.373 (2) Å0.21 × 0.15 × 0.14 mm
β = 94.310 (2)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		7147 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2955 reflections with I > 2σ(I)
Tmin = 0.458, Tmax = 0.577Rint = 0.090
20849 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.057478 parameters
wR(F2) = 0.123H-atom parameters constrained
S = 1.00Δρmax = 0.77 e Å−3
7147 reflectionsΔρmin = −0.75 e Å−3
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
Co10.13607 (7)0.33654 (5)0.33329 (5)0.0563 (3)
Br10.12914 (7)0.62067 (5)0.30379 (5)0.0931 (3)
Br20.56760 (7)0.64339 (5)0.40923 (5)0.0964 (3)
Br30.46208 (6)0.31966 (5)0.21106 (5)0.0806 (3)
Br40.22348 (9)0.36243 (7)−0.04636 (5)0.1212 (4)
N10.2821 (5)0.3226 (4)0.4022 (3)0.0672 (17)
N20.0105 (5)0.3460 (3)0.2508 (4)0.0591 (17)
N30.1000 (8)0.0902 (6)0.3565 (5)0.108 (3)
N4−0.1103 (6)0.4246 (5)0.4558 (4)0.087 (2)
O10.1647 (4)0.4516 (3)0.3353 (2)0.0640 (14)
O20.2388 (4)0.3126 (3)0.2614 (3)0.0689 (14)
O30.0870 (4)0.2193 (4)0.3495 (3)0.0841 (19)
O40.0254 (4)0.3574 (3)0.4115 (3)0.0717 (15)
C10.3594 (6)0.3749 (5)0.4061 (4)0.069 (2)
H10.42800.35840.42380.082*
C20.3489 (6)0.4563 (4)0.3853 (4)0.057 (2)
C30.2534 (7)0.4887 (5)0.3540 (4)0.058 (2)
C40.2571 (6)0.5715 (5)0.3426 (4)0.061 (2)
C50.3470 (7)0.6164 (4)0.3585 (4)0.068 (2)
H50.34490.67010.35030.081*
C60.4417 (6)0.5815 (5)0.3871 (4)0.067 (2)
C70.4430 (6)0.5024 (5)0.4012 (4)0.065 (2)
H70.50610.47920.42140.078*
C80.3173 (7)0.2432 (5)0.4243 (5)0.069 (2)
C90.3873 (7)0.2006 (5)0.3865 (4)0.075 (2)
H90.41520.22300.34780.090*
C100.4171 (7)0.1233 (6)0.4058 (5)0.089 (3)
H100.46470.09500.38020.107*
C110.3740 (7)0.0896 (5)0.4641 (5)0.088 (3)
H110.39070.03830.47710.106*
C120.3050 (7)0.1357 (5)0.5022 (5)0.072 (2)
C130.2740 (6)0.2138 (5)0.4797 (5)0.071 (2)
C140.2018 (6)0.2559 (5)0.5222 (5)0.070 (2)
H140.17900.30620.50950.084*
C150.1672 (7)0.2232 (6)0.5794 (5)0.096 (3)
H150.12340.25270.60670.115*
C160.1938 (8)0.1482 (7)0.5996 (5)0.101 (3)
H160.16510.12640.63830.121*
C170.2620 (8)0.1063 (5)0.5624 (5)0.091 (3)
H170.28150.05610.57720.109*
C180.0265 (6)0.3441 (4)0.1871 (5)0.066 (2)
H18−0.03560.34660.15660.079*
C190.1304 (6)0.3386 (4)0.1554 (4)0.058 (2)
C200.2307 (6)0.3256 (4)0.1960 (5)0.060 (2)
C210.3282 (6)0.3260 (4)0.1587 (4)0.062 (2)
C220.3232 (7)0.3361 (4)0.0892 (5)0.070 (2)
H220.38750.33600.06680.084*
C230.2257 (8)0.3464 (5)0.0510 (4)0.074 (2)
C240.1296 (7)0.3470 (4)0.0833 (5)0.073 (2)
H240.06360.35310.05700.087*
C25−0.1008 (6)0.3546 (5)0.2669 (4)0.064 (2)
C26−0.1549 (7)0.2914 (5)0.2908 (4)0.079 (2)
H26−0.12130.24260.29350.095*
C27−0.2619 (7)0.3004 (6)0.3114 (4)0.085 (3)
H27−0.29830.25740.32800.101*
C28−0.3117 (7)0.3706 (6)0.3071 (4)0.081 (3)
H28−0.38160.37560.32200.098*
C29−0.2612 (7)0.4356 (6)0.2811 (4)0.073 (2)
C30−0.1536 (6)0.4284 (5)0.2599 (4)0.065 (2)
C31−0.1004 (6)0.4969 (5)0.2373 (4)0.073 (2)
H31−0.02880.49380.22500.088*
C32−0.1526 (8)0.5658 (5)0.2338 (5)0.096 (3)
H32−0.11670.61040.21980.115*
C33−0.2614 (9)0.5709 (6)0.2512 (5)0.107 (3)
H33−0.29790.61850.24550.129*
C34−0.3144 (7)0.5091 (6)0.2759 (5)0.092 (3)
H34−0.38500.51470.28930.111*
C350.1276 (9)0.1659 (7)0.3330 (5)0.103 (3)
H350.18210.17050.30250.124*
C360.1576 (10)0.0288 (7)0.3275 (6)0.148 (4)
H36A0.1727−0.01130.36170.222*
H36B0.22500.04850.31240.222*
H36C0.11450.00730.28870.222*
C370.0319 (9)0.0735 (7)0.4061 (7)0.147 (5)
H37A0.06720.03810.43910.220*
H37B−0.03330.04970.38530.220*
H37C0.01340.12100.42910.220*
C38−0.0267 (7)0.4174 (5)0.4162 (4)0.076 (2)
H38−0.00720.46070.39070.091*
C39−0.1474 (8)0.3588 (7)0.4917 (5)0.130 (4)
H39A−0.11880.31180.47270.195*
H39B−0.22570.35720.48700.195*
H39C−0.12290.36270.53980.195*
C40−0.1711 (7)0.4979 (6)0.4565 (5)0.118 (4)
H40A−0.12500.54040.44460.177*
H40B−0.19510.50650.50190.177*
H40C−0.23340.49510.42360.177*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0579 (6)0.0443 (6)0.0663 (7)−0.0026 (5)0.0021 (5)0.0004 (5)
Br10.0924 (7)0.0550 (6)0.1277 (8)0.0024 (5)−0.0203 (6)0.0118 (5)
Br20.0829 (6)0.0771 (6)0.1281 (9)−0.0278 (5)−0.0003 (6)−0.0108 (6)
Br30.0589 (5)0.0855 (7)0.0980 (7)−0.0019 (4)0.0084 (5)−0.0063 (5)
Br40.1367 (9)0.1577 (10)0.0710 (7)0.0335 (8)0.0197 (6)−0.0053 (7)
N10.074 (5)0.050 (4)0.077 (5)−0.002 (4)0.004 (4)0.005 (4)
N20.051 (4)0.053 (4)0.074 (5)0.003 (3)0.009 (4)−0.001 (4)
N30.122 (8)0.070 (7)0.131 (9)−0.004 (6)−0.007 (6)0.021 (6)
N40.082 (6)0.097 (7)0.082 (6)0.006 (5)0.012 (5)−0.009 (5)
O10.063 (3)0.049 (3)0.079 (4)−0.004 (3)0.000 (3)0.002 (3)
O20.061 (3)0.076 (4)0.070 (4)0.010 (3)0.004 (3)−0.002 (3)
O30.079 (4)0.063 (4)0.108 (5)0.014 (3)−0.008 (3)−0.011 (4)
O40.072 (4)0.069 (4)0.074 (4)0.008 (3)0.007 (3)0.001 (3)
C10.067 (5)0.061 (6)0.076 (6)0.001 (5)−0.007 (4)0.002 (5)
C20.062 (5)0.047 (5)0.060 (5)−0.001 (4)0.006 (4)−0.003 (4)
C30.065 (6)0.050 (5)0.059 (5)−0.004 (5)0.010 (5)−0.001 (4)
C40.064 (5)0.054 (5)0.065 (6)−0.004 (4)0.002 (4)0.005 (4)
C50.077 (6)0.050 (5)0.076 (6)−0.013 (5)0.007 (5)0.003 (4)
C60.072 (6)0.057 (6)0.072 (6)−0.016 (4)0.004 (5)−0.010 (4)
C70.063 (5)0.061 (6)0.073 (6)−0.001 (4)0.005 (4)−0.013 (4)
C80.070 (6)0.065 (6)0.072 (7)−0.009 (5)0.000 (5)0.003 (5)
C90.079 (6)0.067 (7)0.080 (7)0.006 (5)0.014 (5)0.000 (5)
C100.092 (7)0.082 (8)0.093 (8)0.014 (6)0.005 (6)−0.014 (6)
C110.091 (7)0.076 (7)0.097 (8)−0.010 (6)−0.003 (6)0.009 (6)
C120.072 (6)0.070 (7)0.073 (7)−0.008 (5)0.002 (5)0.008 (6)
C130.070 (6)0.071 (7)0.071 (7)−0.014 (5)0.004 (5)0.008 (5)
C140.074 (6)0.064 (6)0.072 (6)0.000 (5)0.005 (5)0.014 (5)
C150.101 (7)0.093 (8)0.097 (9)−0.004 (6)0.023 (6)0.011 (6)
C160.102 (8)0.109 (9)0.094 (8)−0.001 (7)0.020 (6)0.023 (7)
C170.092 (7)0.087 (7)0.091 (8)−0.007 (6)−0.006 (6)0.022 (6)
C180.062 (6)0.052 (5)0.083 (7)0.007 (4)−0.002 (5)−0.005 (5)
C190.064 (6)0.052 (5)0.058 (6)0.001 (4)0.002 (5)−0.005 (4)
C200.065 (6)0.051 (5)0.063 (6)0.006 (4)0.009 (5)−0.004 (4)
C210.075 (6)0.052 (5)0.061 (6)0.006 (4)0.013 (5)−0.008 (4)
C220.075 (6)0.068 (6)0.071 (7)0.007 (5)0.024 (5)−0.011 (5)
C230.086 (6)0.072 (6)0.065 (6)0.011 (5)0.008 (6)−0.009 (4)
C240.075 (6)0.073 (6)0.070 (7)0.007 (5)0.002 (5)−0.007 (5)
C250.056 (5)0.057 (6)0.078 (6)−0.001 (5)−0.002 (4)0.004 (4)
C260.061 (6)0.071 (6)0.106 (7)−0.001 (5)0.007 (5)0.007 (5)
C270.067 (6)0.086 (8)0.101 (7)−0.026 (5)0.012 (5)0.013 (6)
C280.065 (6)0.091 (8)0.089 (7)−0.010 (6)0.007 (5)−0.002 (6)
C290.066 (6)0.076 (7)0.078 (6)0.009 (5)0.007 (5)−0.002 (5)
C300.053 (5)0.067 (6)0.075 (6)0.002 (5)0.006 (4)−0.001 (5)
C310.064 (5)0.065 (6)0.092 (7)0.012 (5)0.010 (5)0.010 (5)
C320.085 (7)0.073 (7)0.132 (9)0.016 (6)0.019 (6)0.017 (6)
C330.101 (8)0.086 (8)0.137 (9)0.037 (7)0.018 (7)0.015 (7)
C340.077 (7)0.093 (8)0.110 (8)0.018 (6)0.022 (6)0.003 (6)
C350.105 (8)0.097 (10)0.108 (9)−0.002 (7)0.002 (6)−0.001 (8)
C360.178 (12)0.112 (10)0.155 (12)−0.020 (9)0.018 (9)−0.004 (8)
C370.142 (11)0.142 (11)0.157 (13)−0.002 (9)0.018 (9)−0.041 (9)
C380.072 (6)0.079 (7)0.078 (7)0.004 (5)0.010 (5)−0.006 (5)
C390.132 (9)0.144 (10)0.120 (9)−0.002 (8)0.053 (7)0.016 (8)
C400.106 (8)0.136 (10)0.113 (8)0.035 (7)0.006 (6)−0.041 (7)
Geometric parameters (Å, °) top
Co1—O21.992 (5)C15—C161.371 (11)
Co1—O11.996 (5)C15—H150.9300
Co1—O32.120 (6)C16—C171.350 (11)
Co1—O42.140 (5)C16—H160.9300
Co1—N22.143 (6)C17—H170.9300
Co1—N12.168 (6)C18—C191.461 (10)
Br1—C41.887 (7)C18—H180.9300
Br2—C61.896 (7)C19—C241.405 (9)
Br3—C211.870 (8)C19—C201.429 (10)
Br4—C231.904 (8)C20—C211.444 (9)
N1—C11.301 (8)C21—C221.354 (9)
N1—C81.474 (9)C22—C231.371 (10)
N2—C181.264 (8)C22—H220.9300
N2—C251.433 (8)C23—C241.377 (10)
N3—C371.351 (11)C24—H240.9300
N3—C361.405 (11)C25—C261.365 (9)
N3—C351.420 (12)C25—C301.419 (9)
N4—C381.333 (9)C26—C271.411 (10)
N4—C391.415 (10)C26—H260.9300
N4—C401.457 (10)C27—C281.345 (10)
O1—C31.288 (8)C27—H270.9300
O2—C201.282 (8)C28—C291.384 (10)
O3—C351.098 (10)C28—H280.9300
O4—C381.215 (8)C29—C341.415 (11)
C1—C21.451 (9)C29—C301.420 (9)
C1—H10.9300C30—C311.425 (10)
C2—C31.394 (9)C31—C321.338 (10)
C2—C71.413 (9)C31—H310.9300
C3—C41.433 (9)C32—C331.406 (11)
C4—C51.361 (9)C32—H320.9300
C5—C61.386 (9)C33—C341.346 (11)
C5—H50.9300C33—H330.9300
C6—C71.377 (9)C34—H340.9300
C7—H70.9300C35—H350.9300
C8—C131.333 (10)C36—H36A0.9600
C8—C91.378 (10)C36—H36B0.9600
C9—C101.412 (10)C36—H36C0.9600
C9—H90.9300C37—H37A0.9600
C10—C111.407 (10)C37—H37B0.9600
C10—H100.9300C37—H37C0.9600
C11—C121.407 (10)C38—H380.9300
C11—H110.9300C39—H39A0.9600
C12—C171.408 (11)C39—H39B0.9600
C12—C131.444 (11)C39—H39C0.9600
C13—C141.445 (10)C40—H40A0.9600
C14—C151.338 (10)C40—H40B0.9600
C14—H140.9300C40—H40C0.9600
O2—Co1—O195.51 (19)N2—C18—C19128.1 (8)
O2—Co1—O396.4 (2)N2—C18—H18116.0
O1—Co1—O3167.9 (2)C19—C18—H18116.0
O2—Co1—O4177.7 (2)C24—C19—C20120.4 (7)
O1—Co1—O486.7 (2)C24—C19—C18118.0 (8)
O3—Co1—O481.3 (2)C20—C19—C18121.6 (7)
O2—Co1—N287.3 (2)O2—C20—C19124.8 (7)
O1—Co1—N293.2 (2)O2—C20—C21119.3 (7)
O3—Co1—N289.1 (2)C19—C20—C21115.9 (7)
O4—Co1—N293.2 (2)C22—C21—C20121.4 (7)
O2—Co1—N182.5 (2)C22—C21—Br3121.2 (6)
O1—Co1—N187.7 (2)C20—C21—Br3117.2 (6)
O3—Co1—N192.1 (2)C21—C22—C23121.7 (7)
O4—Co1—N197.1 (2)C21—C22—H22119.1
N2—Co1—N1169.8 (2)C23—C22—H22119.1
C1—N1—C8114.6 (6)C22—C23—C24120.0 (8)
C1—N1—Co1121.7 (5)C22—C23—Br4120.0 (7)
C8—N1—Co1119.4 (5)C24—C23—Br4120.0 (7)
C18—N2—C25115.9 (7)C23—C24—C19120.5 (8)
C18—N2—Co1124.8 (5)C23—C24—H24119.7
C25—N2—Co1119.4 (5)C19—C24—H24119.7
C37—N3—C36119.0 (10)C26—C25—C30120.2 (7)
C37—N3—C35126.5 (11)C26—C25—N2119.4 (7)
C36—N3—C35114.3 (11)C30—C25—N2120.4 (7)
C38—N4—C39120.0 (8)C25—C26—C27119.9 (8)
C38—N4—C40120.2 (9)C25—C26—H26120.1
C39—N4—C40119.5 (8)C27—C26—H26120.1
C3—O1—Co1129.3 (5)C28—C27—C26120.6 (8)
C20—O2—Co1130.5 (5)C28—C27—H27119.7
C35—O3—Co1126.8 (8)C26—C27—H27119.7
C38—O4—Co1124.0 (6)C27—C28—C29121.4 (8)
N1—C1—C2126.4 (7)C27—C28—H28119.3
N1—C1—H1116.8C29—C28—H28119.3
C2—C1—H1116.8C28—C29—C34121.3 (9)
C3—C2—C7121.6 (7)C28—C29—C30119.3 (8)
C3—C2—C1123.7 (7)C34—C29—C30119.4 (9)
C7—C2—C1114.7 (8)C25—C30—C29118.5 (8)
O1—C3—C2126.5 (7)C25—C30—C31122.8 (7)
O1—C3—C4118.5 (7)C29—C30—C31118.5 (8)
C2—C3—C4115.0 (7)C32—C31—C30120.5 (8)
C5—C4—C3123.7 (7)C32—C31—H31119.7
C5—C4—Br1118.6 (6)C30—C31—H31119.7
C3—C4—Br1117.7 (6)C31—C32—C33120.2 (9)
C4—C5—C6119.4 (7)C31—C32—H32119.9
C4—C5—H5120.3C33—C32—H32119.9
C6—C5—H5120.3C34—C33—C32122.0 (9)
C7—C6—C5119.9 (7)C34—C33—H33119.0
C7—C6—Br2120.3 (7)C32—C33—H33119.0
C5—C6—Br2119.8 (6)C33—C34—C29119.2 (9)
C6—C7—C2120.3 (7)C33—C34—H34120.4
C6—C7—H7119.9C29—C34—H34120.4
C2—C7—H7119.9O3—C35—N3122.5 (12)
C13—C8—C9122.1 (9)O3—C35—H35118.7
C13—C8—N1116.9 (8)N3—C35—H35118.7
C9—C8—N1120.8 (8)N3—C36—H36A109.5
C8—C9—C10120.8 (8)N3—C36—H36B109.5
C8—C9—H9119.6H36A—C36—H36B109.5
C10—C9—H9119.6N3—C36—H36C109.5
C11—C10—C9119.3 (8)H36A—C36—H36C109.5
C11—C10—H10120.4H36B—C36—H36C109.5
C9—C10—H10120.4N3—C37—H37A109.5
C12—C11—C10118.1 (9)N3—C37—H37B109.5
C12—C11—H11121.0H37A—C37—H37B109.5
C10—C11—H11121.0N3—C37—H37C109.5
C11—C12—C17120.9 (9)H37A—C37—H37C109.5
C11—C12—C13120.9 (9)H37B—C37—H37C109.5
C17—C12—C13118.2 (9)O4—C38—N4123.7 (9)
C8—C13—C12118.6 (9)O4—C38—H38118.2
C8—C13—C14124.8 (9)N4—C38—H38118.2
C12—C13—C14116.5 (8)N4—C39—H39A109.5
C15—C14—C13120.7 (8)N4—C39—H39B109.5
C15—C14—H14119.6H39A—C39—H39B109.5
C13—C14—H14119.6N4—C39—H39C109.5
C14—C15—C16122.8 (9)H39A—C39—H39C109.5
C14—C15—H15118.6H39B—C39—H39C109.5
C16—C15—H15118.6N4—C40—H40A109.5
C17—C16—C15119.1 (10)N4—C40—H40B109.5
C17—C16—H16120.4H40A—C40—H40B109.5
C15—C16—H16120.4N4—C40—H40C109.5
C16—C17—C12122.6 (9)H40A—C40—H40C109.5
C16—C17—H17118.7H40B—C40—H40C109.5
C12—C17—H17118.7
O2—Co1—N1—C172.8 (6)C10—C11—C12—C17−177.9 (7)
O1—Co1—N1—C1−23.0 (6)C10—C11—C12—C133.6 (12)
O3—Co1—N1—C1169.1 (6)C9—C8—C13—C122.4 (12)
O4—Co1—N1—C1−109.4 (6)N1—C8—C13—C12178.9 (6)
N2—Co1—N1—C172.4 (15)C9—C8—C13—C14178.9 (7)
O2—Co1—N1—C8−82.7 (6)N1—C8—C13—C14−4.6 (11)
O1—Co1—N1—C8−178.5 (6)C11—C12—C13—C8−3.9 (11)
O3—Co1—N1—C813.6 (6)C17—C12—C13—C8177.6 (7)
O4—Co1—N1—C895.1 (6)C11—C12—C13—C14179.3 (7)
N2—Co1—N1—C8−83.1 (14)C17—C12—C13—C140.8 (10)
O2—Co1—N2—C18−7.3 (6)C8—C13—C14—C15−176.0 (8)
O1—Co1—N2—C1888.1 (6)C12—C13—C14—C150.6 (11)
O3—Co1—N2—C18−103.8 (6)C13—C14—C15—C16−2.8 (14)
O4—Co1—N2—C18174.9 (6)C14—C15—C16—C173.5 (15)
N1—Co1—N2—C18−6.9 (17)C15—C16—C17—C12−2.0 (14)
O2—Co1—N2—C25172.2 (5)C11—C12—C17—C16−178.6 (9)
O1—Co1—N2—C25−92.5 (5)C13—C12—C17—C16−0.1 (12)
O3—Co1—N2—C2575.7 (5)C25—N2—C18—C19177.8 (7)
O4—Co1—N2—C25−5.6 (5)Co1—N2—C18—C19−2.7 (11)
N1—Co1—N2—C25172.6 (12)N2—C18—C19—C24−172.4 (7)
O2—Co1—O1—C3−64.5 (6)N2—C18—C19—C207.2 (11)
O3—Co1—O1—C3106.9 (11)Co1—O2—C20—C19−21.0 (10)
O4—Co1—O1—C3114.9 (6)Co1—O2—C20—C21160.2 (5)
N2—Co1—O1—C3−152.1 (6)C24—C19—C20—O2−175.6 (7)
N1—Co1—O1—C317.7 (6)C18—C19—C20—O24.8 (11)
O1—Co1—O2—C20−73.7 (6)C24—C19—C20—C213.1 (9)
O3—Co1—O2—C20108.1 (6)C18—C19—C20—C21−176.5 (6)
O4—Co1—O2—C20120 (5)O2—C20—C21—C22177.1 (7)
N2—Co1—O2—C2019.3 (6)C19—C20—C21—C22−1.7 (10)
N1—Co1—O2—C20−160.6 (6)O2—C20—C21—Br3−7.4 (9)
O2—Co1—O3—C3515.3 (9)C19—C20—C21—Br3173.7 (5)
O1—Co1—O3—C35−156.1 (10)C20—C21—C22—C230.0 (11)
O4—Co1—O3—C35−164.2 (9)Br3—C21—C22—C23−175.2 (6)
N2—Co1—O3—C35102.4 (9)C21—C22—C23—C240.2 (12)
N1—Co1—O3—C35−67.4 (9)C21—C22—C23—Br4178.8 (6)
O2—Co1—O4—C38−162 (5)C22—C23—C24—C191.2 (12)
O1—Co1—O4—C3831.4 (6)Br4—C23—C24—C19−177.3 (5)
O3—Co1—O4—C38−150.3 (6)C20—C19—C24—C23−3.0 (11)
N2—Co1—O4—C38−61.7 (6)C18—C19—C24—C23176.6 (7)
N1—Co1—O4—C38118.7 (6)C18—N2—C25—C26105.7 (8)
C8—N1—C1—C2177.4 (7)Co1—N2—C25—C26−73.8 (8)
Co1—N1—C1—C220.8 (10)C18—N2—C25—C30−76.0 (9)
N1—C1—C2—C3−4.1 (12)Co1—N2—C25—C30104.5 (7)
N1—C1—C2—C7174.1 (7)C30—C25—C26—C27−2.7 (12)
Co1—O1—C3—C2−8.2 (11)N2—C25—C26—C27175.6 (7)
Co1—O1—C3—C4172.3 (5)C25—C26—C27—C280.5 (13)
C7—C2—C3—O1177.6 (6)C26—C27—C28—C291.5 (13)
C1—C2—C3—O1−4.4 (12)C27—C28—C29—C34179.2 (8)
C7—C2—C3—C4−2.8 (10)C27—C28—C29—C30−1.4 (12)
C1—C2—C3—C4175.2 (6)C26—C25—C30—C292.8 (11)
O1—C3—C4—C5−178.3 (7)N2—C25—C30—C29−175.5 (7)
C2—C3—C4—C52.1 (10)C26—C25—C30—C31177.9 (7)
O1—C3—C4—Br12.1 (9)N2—C25—C30—C31−0.4 (12)
C2—C3—C4—Br1−177.5 (5)C28—C29—C30—C25−0.7 (11)
C3—C4—C5—C60.3 (11)C34—C29—C30—C25178.7 (7)
Br1—C4—C5—C6179.9 (5)C28—C29—C30—C31−176.1 (7)
C4—C5—C6—C7−2.2 (11)C34—C29—C30—C313.3 (12)
C4—C5—C6—Br2179.8 (5)C25—C30—C31—C32−177.7 (8)
C5—C6—C7—C21.4 (11)C29—C30—C31—C32−2.5 (12)
Br2—C6—C7—C2179.5 (5)C30—C31—C32—C33−1.2 (14)
C3—C2—C7—C61.2 (11)C31—C32—C33—C344.3 (15)
C1—C2—C7—C6−177.0 (7)C32—C33—C34—C29−3.4 (15)
C1—N1—C8—C13116.2 (8)C28—C29—C34—C33179.0 (9)
Co1—N1—C8—C13−86.6 (8)C30—C29—C34—C33−0.4 (13)
C1—N1—C8—C9−67.2 (9)Co1—O3—C35—N3168.7 (6)
Co1—N1—C8—C990.0 (8)C37—N3—C35—O3−7.6 (17)
C13—C8—C9—C10−0.7 (12)C36—N3—C35—O3177.5 (11)
N1—C8—C9—C10−177.1 (7)Co1—O4—C38—N4166.4 (6)
C8—C9—C10—C110.4 (12)C39—N4—C38—O4−4.2 (13)
C9—C10—C11—C12−1.9 (12)C40—N4—C38—O4−177.7 (8)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C21a—H28b···Br3a0.9302.9321.870151.6
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C21a—H28b···Br3a0.9302.9321.870151.6
references
References top

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Bruker (2001). SAINT (Version 6.45) and SMART (Version 5.0). Bruker AXS Inc., Madison, Wisconsin, USA.

El-Behery, M. & El-Twigry, H. (2007). Spectrochim. Acta Part A, 66, 28–36.

Erçağ, A., Yildırım, S. Ö. & Akkurt, M. (2006). Chin. Chem. Lett. 17, 243–246.

Mostafa, E. B. & Haifaa, E. T. (2007). Spectrochim. Acta Part A, 66, 28–36.

Musie, G. T., Li, X. B. & Powell, D. R. (2003). Inorg. Chim. Acta, 348, 69–74.

Patel, R. N., Nripendra Singh, V. L. N. & Gundla, R. N. (2006). Polyhedron, 25, 3312–3318.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.