Bis{2,4-dibromo-6-[(2-phenyl-eth-yl)imino-meth-yl]phenolato-κN,O}cobalt(II).

In the title complex, [Co(C(15)H(12)Br(2)NO)(2)], the Co(II) atom is four-coordinated by two N,O-bidentate chelate Schiff base ligands, displaying a flattened tetra-hedral coordination environment. The Co(II) atom occupies a special position on a twofold rotation axis. In the crystal, mol-ecules are linked via weak C-H⋯Br inter-actions.

Related literature

For background to vitamin B12, see: Randaccio et al. (2010 ▶). For the anti­tumour activity of Schiff base–metal complexes, see: Ren et al. (2002 ▶) and for their anti-microbial activity, see: Panneerselvam et al. (2005 ▶). For related structures, see: Chen et al. (2010 ▶); Li et al. (2010 ▶); Jiang et al. (2008 ▶); For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[Co(C15H12Br2NO)2]

M = 823.08

Monoclinic,

a = 22.5087 (16) Å

b = 4.8717 (4) Å

c = 28.864 (2) Å

β = 111.505 (1)°

V = 2944.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 6.04 mm−1

T = 291 K

0.24 × 0.23 × 0.22 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.325, T max = 0.350

14453 measured reflections

2876 independent reflections

2478 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.108

S = 1.01

2876 reflections

177 parameters

H-atom parameters constrained

Δρmax = 0.79 e Å−3

Δρmin = −0.78 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus (Bruker, 2000 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681104459X/br2176sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104459X/br2176Isup2.hkl

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

[Co(C15H12Br2NO)2]	F(000) = 1604
Mr = 823.08	Dx = 1.857 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5864 reflections
a = 22.5087 (16) Å	θ = 2.9–28.1°
b = 4.8717 (4) Å	µ = 6.04 mm−1
c = 28.864 (2) Å	T = 291 K
β = 111.505 (1)°	Block, red
V = 2944.8 (4) Å3	0.24 × 0.23 × 0.22 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2876 independent reflections
Radiation source: fine-focus sealed tube	2478 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −27→27
Tmin = 0.325, Tmax = 0.350	k = −6→6
14453 measured reflections	l = −35→35

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.082P)2 + 0.812P] where P = (Fo2 + 2Fc2)/3
2876 reflections	(Δ/σ)max < 0.001
177 parameters	Δρmax = 0.79 e Å−3
0 restraints	Δρmin = −0.78 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
C1	0.12749 (15)	0.3862 (7)	0.22685 (12)	0.0389 (7)
C2	0.08497 (15)	0.5880 (6)	0.19768 (11)	0.0367 (7)
C3	0.09703 (15)	0.6772 (6)	0.15481 (11)	0.0365 (6)
C4	0.14508 (15)	0.5753 (6)	0.14172 (12)	0.0409 (7)
H4	0.1509	0.6379	0.1132	0.049*
C5	0.18509 (15)	0.3773 (7)	0.17151 (12)	0.0430 (7)
C6	0.17739 (16)	0.2844 (7)	0.21350 (12)	0.0435 (8)
H6	0.2052	0.1534	0.2333	0.052*
C7	0.12310 (17)	0.2717 (7)	0.27173 (12)	0.0431 (7)
H7	0.1561	0.1560	0.2903	0.052*
C8	0.08535 (19)	0.1846 (8)	0.33657 (12)	0.0492 (8)
H8A	0.1125	0.0239	0.3418	0.059*
H8B	0.0438	0.1257	0.3358	0.059*
C9	0.1142 (2)	0.3836 (9)	0.37889 (14)	0.0656 (11)
H9A	0.0876	0.5464	0.3729	0.079*
H9B	0.1560	0.4390	0.3799	0.079*
C10	0.12060 (19)	0.2619 (7)	0.42885 (13)	0.0503 (9)
C11	0.0790 (2)	0.3341 (10)	0.45192 (14)	0.0613 (10)
H11	0.0479	0.4661	0.4374	0.074*
C12	0.0828 (3)	0.2136 (10)	0.49615 (16)	0.0701 (12)
H12	0.0536	0.2616	0.5107	0.084*
C13	0.1281 (3)	0.0287 (10)	0.51828 (15)	0.0702 (12)
H13	0.1309	−0.0479	0.5485	0.084*
C14	0.1703 (3)	−0.0485 (13)	0.49693 (19)	0.0972 (19)
H14	0.2012	−0.1803	0.5121	0.117*
C15	0.1668 (2)	0.0710 (11)	0.45224 (17)	0.0773 (14)
H15	0.1962	0.0209	0.4380	0.093*
Br1	0.040636 (17)	0.94006 (7)	0.113456 (12)	0.04757 (15)
Br2	0.250012 (17)	0.22456 (9)	0.151646 (14)	0.05805 (16)
Co1	0.0000	0.52246 (15)	0.2500	0.04521 (19)
N1	0.07834 (13)	0.3134 (6)	0.28853 (10)	0.0425 (6)
O1	0.03706 (12)	0.6888 (5)	0.20677 (9)	0.0468 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0389 (16)	0.0510 (18)	0.0320 (16)	−0.0033 (13)	0.0192 (13)	−0.0013 (13)
C2	0.0394 (16)	0.0439 (17)	0.0338 (16)	−0.0048 (12)	0.0219 (13)	−0.0012 (12)
C3	0.0406 (16)	0.0432 (16)	0.0303 (15)	−0.0029 (13)	0.0182 (13)	0.0005 (12)
C4	0.0460 (18)	0.0523 (19)	0.0324 (16)	−0.0078 (15)	0.0239 (14)	−0.0023 (13)
C5	0.0360 (16)	0.0589 (19)	0.0414 (18)	−0.0039 (14)	0.0226 (14)	−0.0086 (15)
C6	0.0364 (16)	0.059 (2)	0.0370 (17)	0.0031 (14)	0.0155 (14)	0.0028 (14)
C7	0.0444 (18)	0.0548 (19)	0.0336 (16)	0.0020 (14)	0.0184 (14)	0.0063 (14)
C8	0.054 (2)	0.064 (2)	0.0345 (17)	−0.0061 (17)	0.0213 (15)	0.0100 (15)
C9	0.091 (3)	0.069 (2)	0.038 (2)	−0.021 (2)	0.026 (2)	0.0042 (17)
C10	0.062 (2)	0.057 (2)	0.0324 (17)	−0.0141 (17)	0.0174 (16)	−0.0011 (14)
C11	0.067 (2)	0.074 (3)	0.040 (2)	0.005 (2)	0.0150 (18)	0.0093 (18)
C12	0.089 (3)	0.087 (3)	0.044 (2)	0.001 (3)	0.035 (2)	−0.004 (2)
C13	0.095 (3)	0.083 (3)	0.036 (2)	0.004 (3)	0.027 (2)	0.0095 (19)
C14	0.114 (4)	0.133 (5)	0.050 (3)	0.052 (4)	0.036 (3)	0.032 (3)
C15	0.076 (3)	0.116 (4)	0.047 (2)	0.022 (3)	0.032 (2)	0.013 (2)
Br1	0.0584 (2)	0.0515 (2)	0.0413 (2)	0.00711 (15)	0.02841 (17)	0.00863 (13)
Br2	0.0447 (2)	0.0830 (3)	0.0575 (3)	0.00539 (17)	0.03169 (19)	−0.00833 (18)
Co1	0.0441 (4)	0.0638 (4)	0.0359 (4)	0.000	0.0243 (3)	0.000
N1	0.0470 (16)	0.0554 (16)	0.0312 (14)	−0.0017 (13)	0.0216 (12)	0.0052 (12)
O1	0.0522 (14)	0.0575 (14)	0.0442 (13)	0.0103 (11)	0.0337 (11)	0.0089 (11)

C1—C6	1.405 (5)	C9—C10	1.516 (5)
C1—C2	1.415 (5)	C9—H9A	0.9700
C1—C7	1.447 (4)	C9—H9B	0.9700
C2—O1	1.296 (4)	C10—C15	1.374 (6)
C2—C3	1.428 (4)	C10—C11	1.378 (6)
C3—C4	1.363 (4)	C11—C12	1.379 (6)
C3—Br1	1.888 (3)	C11—H11	0.9300
C4—C5	1.383 (5)	C12—C13	1.335 (7)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.363 (5)	C13—C14	1.360 (7)
C5—Br2	1.906 (3)	C13—H13	0.9300
C6—H6	0.9300	C14—C15	1.391 (7)
C7—N1	1.284 (4)	C14—H14	0.9300
C7—H7	0.9300	C15—H15	0.9300
C8—N1	1.477 (4)	Co1—O1	1.916 (2)
C8—C9	1.507 (5)	Co1—O1i	1.916 (2)
C8—H8A	0.9700	Co1—N1	1.986 (3)
C8—H8B	0.9700	Co1—N1i	1.986 (3)
C6—C1—C2	121.1 (3)	C10—C9—H9B	109.1
C6—C1—C7	115.7 (3)	H9A—C9—H9B	107.8
C2—C1—C7	123.2 (3)	C15—C10—C11	117.4 (3)
O1—C2—C1	125.0 (3)	C15—C10—C9	121.6 (4)
O1—C2—C3	119.8 (3)	C11—C10—C9	121.0 (4)
C1—C2—C3	115.2 (3)	C10—C11—C12	121.1 (4)
C4—C3—C2	123.5 (3)	C10—C11—H11	119.5
C4—C3—Br1	119.3 (2)	C12—C11—H11	119.5
C2—C3—Br1	117.2 (2)	C13—C12—C11	120.5 (4)
C3—C4—C5	118.9 (3)	C13—C12—H12	119.8
C3—C4—H4	120.5	C11—C12—H12	119.8
C5—C4—H4	120.5	C12—C13—C14	120.5 (4)
C6—C5—C4	121.2 (3)	C12—C13—H13	119.8
C6—C5—Br2	120.0 (3)	C14—C13—H13	119.8
C4—C5—Br2	118.8 (2)	C13—C14—C15	119.5 (5)
C5—C6—C1	120.1 (3)	C13—C14—H14	120.2
C5—C6—H6	119.9	C15—C14—H14	120.2
C1—C6—H6	119.9	C10—C15—C14	121.0 (5)
N1—C7—C1	126.7 (3)	C10—C15—H15	119.5
N1—C7—H7	116.7	C14—C15—H15	119.5
C1—C7—H7	116.7	O1—Co1—O1i	129.98 (15)
N1—C8—C9	110.7 (3)	O1—Co1—N1	94.15 (10)
N1—C8—H8A	109.5	O1i—Co1—N1	111.18 (11)
C9—C8—H8A	109.5	O1—Co1—N1i	111.18 (11)
N1—C8—H8B	109.5	O1i—Co1—N1i	94.14 (10)
C9—C8—H8B	109.5	N1—Co1—N1i	118.31 (17)
H8A—C8—H8B	108.1	C7—N1—C8	117.3 (3)
C8—C9—C10	112.5 (3)	C7—N1—Co1	121.9 (2)
C8—C9—H9A	109.1	C8—N1—Co1	120.7 (2)
C10—C9—H9A	109.1	C2—O1—Co1	124.4 (2)
C8—C9—H9B	109.1

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Br2ii	0.93	3.01	3.940 (3)	173.
C8—H8B···Br1iii	0.97	2.93	3.814 (3)	151.
C9—H9B···Br2iv	0.97	2.94	3.854 (3)	157.

Table 1

Selected bond lengths (Å)

Co1—O1	1.916 (2)
Co1—N1	1.986 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯Br2i	0.93	3.01	3.940 (3)	173
C8—H8B⋯Br1ii	0.97	2.93	3.814 (3)	151
C9—H9B⋯Br2iii	0.97	2.94	3.854 (3)	157

Symmetry codes: (i) ; (ii) ; (iii) .