Tris[4-bromo-2-(methyl-imino-meth-yl)phenolato-κ(2) N,O]cobalt(III).

In the title compound, [Co(C8H7BrNO)3], the Co(III) ion is coordinated in a slightly distorted octa-hedral environment by three N atoms and three O atoms from three bidentate 4-bromo-2-(methyl-imino-meth-yl)phenolate ligands. The dihedral angles between the benzene rings are 82.6 (2), 57.1 (2) and 62.9 (2)°. In the crystal, mol-ecules are linked by pairs of weak C-H⋯Br hydrogen bonds, forming inversion dimers.

Related literature

For applications of Schiff base n class="Chemical">complexes, see: Pradeep & Das (2013 ▶); Shankara et al. (2013 ▶); Feng et al. (2007 ▶); Yang et al. (2007 ▶); Raptopoulou et al. (2006 ▶); Zhang & Feng (2010 ▶); Qin et al. (2009 ▶). For related structures, see: Park et al. (2008 ▶); Huang et al. (2011 ▶, 2012 ▶).

Experimental

Crystal data

[Co(C8H7BrNO)3]

M = 698.10

Orthorhombic,

a = 17.1086 (6) Å

b = 15.0188 (4) Å

c = 19.9578 (7) Å

V = 5128.2 (3) Å3

Z = 8

Mo Kα radiation

μ = 5.38 mm−1

T = 293 K

0.18 × 0.16 × 0.14 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.282, T max = 1.000

15312 measured reflections

4558 independent reflections

3104 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.089

S = 1.01

4558 reflections

310 parameters

H-atom parameters constrained

Δρmax = 0.82 e Å−3

Δρmin = −0.75 e Å−3

Data collection: SMART (Bruker 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813027591/lh5657sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813027591/lh5657Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813027591/lh5657Isup3.cdx

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

[Co(C8H7BrNO)3]	F(000) = 2736
Mr = 698.10	Dx = 1.808 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4287 reflections
a = 17.1086 (6) Å	θ = 2.9–29.1°
b = 15.0188 (4) Å	µ = 5.38 mm−1
c = 19.9578 (7) Å	T = 293 K
V = 5128.2 (3) Å3	Block, brown
Z = 8	0.18 × 0.16 × 0.14 mm

Bruker SMART CCD diffractometer	4558 independent reflections
Radiation source: fine-focus sealed tube	3104 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: no pixels mm-1	θmax = 25.1°, θmin = 2.9°
ω scans	h = −19→20
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −17→17
Tmin = 0.282, Tmax = 1.000	l = −22→23
15312 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.030P)2 + 7.4066P] where P = (Fo2 + 2Fc2)/3
4558 reflections	(Δ/σ)max < 0.001
310 parameters	Δρmax = 0.82 e Å−3
0 restraints	Δρmin = −0.75 e Å−3

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.

	x	y	z	Uiso*/Ueq
Br1	0.42428 (4)	0.69768 (5)	0.48113 (3)	0.0903 (2)
Br2	0.19400 (4)	0.72733 (4)	−0.03750 (3)	0.0880 (2)
Br3	0.45860 (4)	0.03597 (4)	0.40953 (3)	0.0764 (2)
C1	0.3526 (2)	0.5538 (2)	0.2818 (2)	0.0346 (10)
C2	0.4091 (3)	0.6212 (3)	0.2826 (2)	0.0422 (11)
H2	0.4324	0.6387	0.2426	0.051*
C3	0.4310 (3)	0.6622 (3)	0.3414 (3)	0.0492 (12)
H3	0.4684	0.7071	0.3409	0.059*
C4	0.3973 (3)	0.6367 (3)	0.4009 (2)	0.0529 (13)
C5	0.3430 (3)	0.5699 (3)	0.4029 (2)	0.0503 (12)
H5	0.3207	0.5534	0.4435	0.060*
C6	0.3210 (3)	0.5265 (3)	0.3439 (2)	0.0409 (11)
C7	0.2603 (3)	0.4607 (3)	0.3472 (2)	0.0457 (12)
H7	0.2331	0.4560	0.3874	0.055*
C8	0.1706 (3)	0.3516 (3)	0.3114 (3)	0.0638 (15)
H8A	0.1482	0.3657	0.3542	0.096*
H8B	0.1856	0.2900	0.3106	0.096*
H8C	0.1327	0.3625	0.2768	0.096*
C9	0.2016 (3)	0.5015 (3)	0.1256 (2)	0.0432 (11)
C10	0.1327 (3)	0.5518 (3)	0.1133 (3)	0.0553 (13)
H10	0.0884	0.5414	0.1392	0.066*
C11	0.1304 (3)	0.6153 (3)	0.0641 (3)	0.0651 (16)
H11	0.0847	0.6472	0.0566	0.078*
C12	0.1959 (3)	0.6321 (3)	0.0255 (3)	0.0562 (14)
C13	0.2619 (3)	0.5815 (3)	0.0326 (2)	0.0496 (12)
H13	0.3047	0.5912	0.0049	0.060*
C14	0.2648 (3)	0.5150 (3)	0.0818 (2)	0.0396 (11)
C15	0.3322 (3)	0.4577 (3)	0.0834 (2)	0.0389 (10)
H15	0.3662	0.4608	0.0471	0.047*
C16	0.4181 (3)	0.3453 (3)	0.1208 (3)	0.0512 (13)
H16A	0.4374	0.3515	0.0758	0.077*
H16B	0.4036	0.2844	0.1286	0.077*
H16C	0.4583	0.3623	0.1519	0.077*
C17	0.4012 (2)	0.2962 (3)	0.2891 (2)	0.0375 (10)
C18	0.4649 (3)	0.2921 (3)	0.3340 (2)	0.0446 (11)
H18	0.4960	0.3422	0.3406	0.054*
C19	0.4814 (3)	0.2151 (3)	0.3681 (2)	0.0480 (12)
H19	0.5230	0.2135	0.3980	0.058*
C20	0.4367 (3)	0.1399 (3)	0.3582 (2)	0.0470 (12)
C21	0.3765 (3)	0.1399 (3)	0.3132 (2)	0.0456 (12)
H21	0.3481	0.0880	0.3058	0.055*
C22	0.3573 (3)	0.2179 (3)	0.2782 (2)	0.0380 (10)
C23	0.2951 (3)	0.2142 (3)	0.2299 (2)	0.0403 (11)
H23	0.2753	0.1581	0.2200	0.048*
C24	0.2037 (3)	0.2610 (3)	0.1494 (3)	0.0543 (13)
H24A	0.1961	0.1978	0.1464	0.081*
H24B	0.2196	0.2837	0.1066	0.081*
H24C	0.1556	0.2889	0.1627	0.081*
Co1	0.29471 (3)	0.40287 (3)	0.21453 (3)	0.03520 (16)
N1	0.2399 (2)	0.4078 (2)	0.29993 (18)	0.0424 (9)
N2	0.2642 (2)	0.2802 (2)	0.19908 (18)	0.0389 (9)
N3	0.34932 (18)	0.4031 (2)	0.13001 (17)	0.0351 (8)
O1	0.32936 (17)	0.52222 (16)	0.22408 (14)	0.0401 (7)
O2	0.20115 (16)	0.44434 (19)	0.17475 (16)	0.0457 (8)
O3	0.38751 (16)	0.37176 (17)	0.25932 (14)	0.0409 (7)

	U11	U22	U33	U12	U13	U23
Br1	0.0634 (4)	0.1341 (6)	0.0734 (4)	−0.0235 (4)	0.0026 (4)	−0.0567 (4)
Br2	0.1194 (6)	0.0797 (4)	0.0650 (4)	0.0317 (4)	−0.0267 (4)	0.0175 (3)
Br3	0.0879 (4)	0.0639 (3)	0.0773 (4)	0.0232 (3)	0.0011 (4)	0.0260 (3)
C1	0.038 (2)	0.024 (2)	0.042 (3)	0.0048 (19)	−0.002 (2)	−0.0038 (19)
C2	0.043 (3)	0.038 (2)	0.045 (3)	0.001 (2)	0.004 (2)	0.000 (2)
C3	0.040 (3)	0.047 (3)	0.061 (3)	−0.006 (2)	0.000 (3)	−0.011 (2)
C4	0.044 (3)	0.064 (3)	0.051 (3)	−0.003 (3)	−0.006 (3)	−0.023 (3)
C5	0.048 (3)	0.063 (3)	0.040 (3)	−0.002 (3)	0.003 (3)	−0.010 (2)
C6	0.041 (3)	0.039 (2)	0.043 (3)	−0.002 (2)	0.004 (2)	−0.004 (2)
C7	0.049 (3)	0.045 (3)	0.043 (3)	−0.002 (2)	0.007 (3)	0.000 (2)
C8	0.067 (3)	0.057 (3)	0.068 (4)	−0.024 (3)	0.022 (3)	−0.014 (3)
C9	0.043 (3)	0.039 (2)	0.048 (3)	0.008 (2)	−0.013 (3)	−0.011 (2)
C10	0.045 (3)	0.055 (3)	0.066 (4)	0.008 (3)	−0.004 (3)	−0.013 (3)
C11	0.060 (4)	0.060 (3)	0.075 (4)	0.019 (3)	−0.025 (3)	−0.009 (3)
C12	0.070 (4)	0.048 (3)	0.051 (3)	0.014 (3)	−0.027 (3)	−0.002 (2)
C13	0.058 (3)	0.058 (3)	0.032 (3)	0.009 (3)	−0.013 (3)	−0.003 (2)
C14	0.044 (3)	0.042 (3)	0.033 (2)	0.007 (2)	−0.007 (2)	−0.007 (2)
C15	0.041 (3)	0.041 (2)	0.035 (3)	0.002 (2)	0.000 (2)	−0.005 (2)
C16	0.041 (3)	0.044 (3)	0.069 (3)	0.009 (2)	0.011 (3)	0.003 (2)
C17	0.036 (2)	0.043 (3)	0.034 (2)	0.000 (2)	0.002 (2)	−0.003 (2)
C18	0.046 (3)	0.044 (3)	0.043 (3)	−0.003 (2)	−0.003 (3)	−0.004 (2)
C19	0.047 (3)	0.055 (3)	0.042 (3)	0.010 (2)	−0.004 (3)	−0.005 (2)
C20	0.058 (3)	0.044 (3)	0.038 (3)	0.021 (3)	0.012 (3)	0.007 (2)
C21	0.051 (3)	0.038 (2)	0.047 (3)	0.005 (2)	0.012 (3)	0.002 (2)
C22	0.041 (2)	0.035 (2)	0.038 (3)	0.000 (2)	0.003 (2)	−0.002 (2)
C23	0.043 (3)	0.030 (2)	0.048 (3)	−0.007 (2)	0.006 (3)	−0.008 (2)
C24	0.051 (3)	0.052 (3)	0.060 (3)	−0.004 (3)	−0.016 (3)	−0.012 (2)
Co1	0.0362 (3)	0.0308 (3)	0.0386 (3)	−0.0002 (3)	−0.0013 (3)	−0.0029 (2)
N1	0.046 (2)	0.036 (2)	0.044 (2)	−0.0077 (18)	0.003 (2)	−0.0010 (18)
N2	0.036 (2)	0.040 (2)	0.040 (2)	−0.0007 (17)	−0.0041 (19)	−0.0048 (17)
N3	0.0316 (19)	0.0326 (18)	0.041 (2)	0.0023 (16)	−0.0029 (18)	−0.0053 (17)
O1	0.0511 (18)	0.0315 (15)	0.0379 (18)	−0.0013 (14)	−0.0001 (16)	−0.0016 (13)
O2	0.0368 (17)	0.0480 (17)	0.052 (2)	0.0055 (15)	0.0010 (17)	−0.0023 (16)
O3	0.0433 (17)	0.0314 (15)	0.0480 (18)	−0.0062 (14)	−0.0108 (16)	0.0041 (14)

Br1—C4	1.902 (4)	C14—C15	1.438 (6)
Br2—C12	1.904 (5)	C15—N3	1.275 (5)
Br3—C20	1.904 (4)	C15—H15	0.9300
C1—O1	1.308 (5)	C16—N3	1.475 (5)
C1—C2	1.400 (6)	C16—H16A	0.9600
C1—C6	1.413 (6)	C16—H16B	0.9600
C2—C3	1.377 (6)	C16—H16C	0.9600
C2—H2	0.9300	C17—O3	1.302 (5)
C3—C4	1.374 (6)	C17—C22	1.412 (6)
C3—H3	0.9300	C17—C18	1.413 (6)
C4—C5	1.368 (6)	C18—C19	1.371 (6)
C5—C6	1.396 (6)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.378 (6)
C6—C7	1.436 (6)	C19—H19	0.9300
C7—N1	1.281 (5)	C20—C21	1.367 (6)
C7—H7	0.9300	C21—C22	1.404 (6)
C8—N1	1.474 (5)	C21—H21	0.9300
C8—H8A	0.9600	C22—C23	1.437 (6)
C8—H8B	0.9600	C23—N2	1.281 (5)
C8—H8C	0.9600	C23—H23	0.9300
C9—O2	1.304 (5)	C24—N2	1.462 (5)
C9—C14	1.404 (6)	C24—H24A	0.9600
C9—C10	1.421 (6)	C24—H24B	0.9600
C10—C11	1.370 (7)	C24—H24C	0.9600
C10—H10	0.9300	Co1—O3	1.881 (3)
C11—C12	1.383 (7)	Co1—O2	1.892 (3)
C11—H11	0.9300	Co1—O1	1.898 (3)
C12—C13	1.369 (6)	Co1—N3	1.928 (3)
C13—C14	1.402 (6)	Co1—N2	1.939 (3)
C13—H13	0.9300	Co1—N1	1.946 (4)
O1—C1—C2	118.8 (4)	O3—C17—C22	124.0 (4)
O1—C1—C6	123.5 (4)	O3—C17—C18	117.8 (4)
C2—C1—C6	117.6 (4)	C22—C17—C18	118.2 (4)
C3—C2—C1	121.3 (4)	C19—C18—C17	120.6 (4)
C3—C2—H2	119.3	C19—C18—H18	119.7
C1—C2—H2	119.3	C17—C18—H18	119.7
C4—C3—C2	119.9 (4)	C18—C19—C20	120.5 (4)
C4—C3—H3	120.1	C18—C19—H19	119.8
C2—C3—H3	120.1	C20—C19—H19	119.8
C5—C4—C3	121.0 (4)	C21—C20—C19	120.8 (4)
C5—C4—Br1	119.6 (4)	C21—C20—Br3	120.1 (4)
C3—C4—Br1	119.4 (4)	C19—C20—Br3	119.1 (4)
C4—C5—C6	120.0 (4)	C20—C21—C22	120.3 (4)
C4—C5—H5	120.0	C20—C21—H21	119.9
C6—C5—H5	120.0	C22—C21—H21	119.9
C5—C6—C1	120.1 (4)	C21—C22—C17	119.6 (4)
C5—C6—C7	118.5 (4)	C21—C22—C23	118.3 (4)
C1—C6—C7	121.1 (4)	C17—C22—C23	122.1 (4)
N1—C7—C6	126.2 (4)	N2—C23—C22	126.7 (4)
N1—C7—H7	116.9	N2—C23—H23	116.7
C6—C7—H7	116.9	C22—C23—H23	116.7
N1—C8—H8A	109.5	N2—C24—H24A	109.5
N1—C8—H8B	109.5	N2—C24—H24B	109.5
H8A—C8—H8B	109.5	H24A—C24—H24B	109.5
N1—C8—H8C	109.5	N2—C24—H24C	109.5
H8A—C8—H8C	109.5	H24A—C24—H24C	109.5
H8B—C8—H8C	109.5	H24B—C24—H24C	109.5
O2—C9—C14	124.6 (4)	O3—Co1—O2	174.38 (12)
O2—C9—C10	118.3 (4)	O3—Co1—O1	85.60 (12)
C14—C9—C10	117.1 (4)	O2—Co1—O1	89.74 (12)
C11—C10—C9	121.1 (5)	O3—Co1—N3	90.42 (13)
C11—C10—H10	119.4	O2—Co1—N3	92.41 (14)
C9—C10—H10	119.4	O1—Co1—N3	86.25 (13)
C10—C11—C12	120.3 (5)	O3—Co1—N2	93.85 (13)
C10—C11—H11	119.9	O2—Co1—N2	91.03 (14)
C12—C11—H11	119.9	O1—Co1—N2	175.83 (14)
C13—C12—C11	120.6 (5)	N3—Co1—N2	89.62 (14)
C13—C12—Br2	120.0 (4)	O3—Co1—N1	89.98 (14)
C11—C12—Br2	119.4 (4)	O2—Co1—N1	87.00 (14)
C12—C13—C14	119.9 (5)	O1—Co1—N1	91.51 (13)
C12—C13—H13	120.1	N3—Co1—N1	177.69 (14)
C14—C13—H13	120.1	N2—Co1—N1	92.63 (14)
C13—C14—C9	120.7 (4)	C7—N1—C8	117.3 (4)
C13—C14—C15	118.0 (4)	C7—N1—Co1	122.5 (3)
C9—C14—C15	121.2 (4)	C8—N1—Co1	120.1 (3)
N3—C15—C14	125.8 (4)	C23—N2—C24	117.7 (4)
N3—C15—H15	117.1	C23—N2—Co1	123.2 (3)
C14—C15—H15	117.1	C24—N2—Co1	119.1 (3)
N3—C16—H16A	109.5	C15—N3—C16	118.1 (4)
N3—C16—H16B	109.5	C15—N3—Co1	121.9 (3)
H16A—C16—H16B	109.5	C16—N3—Co1	119.7 (3)
N3—C16—H16C	109.5	C1—O1—Co1	121.8 (2)
H16A—C16—H16C	109.5	C9—O2—Co1	121.8 (3)
H16B—C16—H16C	109.5	C17—O3—Co1	125.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···Br1i	0.93	2.90	3.657 (4)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯Br1i	0.93	2.90	3.657 (4)	140

Symmetry code: (i) .