Bis{2-bromo-4-chloro-6-[(E)-(2,6-di-methyl-phen-yl)imino-meth-yl]phenolato-κ(2) N,O}cobalt(II).

In the title complex, [Co(C15H12BrClNO)2], the Co(II) ion is coordinated by two N,O-bidentate 2-bromo-4-chloro-6-[(E)-(2,6-dimethyl-phen-yl)imino-meth-yl]phenolate ligands, generating a squashed CoN2O2 tetra-hedral coordination geometry. The dihedral angles between the aromatic rings in the ligands are 82.60 (14) and 71.79 (14)°. The complex has approximate local noncrystallographic twofold symmetry. In the crystal, weak aromatic π-π stacking is observed [centroid-centroid separation = 3.6434 (18) Å].

Related literature

For background to Schiff bases, see: Billson et al. (2000 ▶); Carlton et al. (1995 ▶); Feng et al. (2008 ▶); Liu et al. (2009 ▶).

Experimental

Crystal data

[Co(C15H12BrClNO)2]

M = 734.16

Monoclinic,

a = 11.608 (2) Å

b = 24.157 (4) Å

c = 11.354 (2) Å

β = 114.380 (2)°

V = 2899.8 (9) Å3

Z = 4

Mo Kα radiation

μ = 3.56 mm−1

T = 153 K

0.49 × 0.27 × 0.12 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ▶) T min = 0.274, T max = 0.683

32947 measured reflections

7718 independent reflections

6813 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.119

S = 1.00

7718 reflections

356 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.63 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813003747/hb7032sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813003747/hb7032Isup2.hkl

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

[Co(C15H12BrClNO)2]	F(000) = 1460
Mr = 734.16	Dx = 1.682 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.608 (2) Å	Cell parameters from 10097 reflections
b = 24.157 (4) Å	θ = 2.1–29.1°
c = 11.354 (2) Å	µ = 3.56 mm−1
β = 114.380 (2)°	T = 153 K
V = 2899.8 (9) Å3	Chunk, red
Z = 4	0.49 × 0.27 × 0.12 mm

Rigaku AFC10/Saturn724+ diffractometer	7718 independent reflections
Radiation source: Rotating Anode	6813 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 28.5714 pixels mm-1	θmax = 29.1°, θmin = 2.3°
phi and ω scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −33→32
Tmin = 0.274, Tmax = 0.683	l = −15→15
32947 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0651P)2 + 0.516P] where P = (Fo2 + 2Fc2)/3
7718 reflections	(Δ/σ)max = 0.002
356 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.63 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
Co1	0.26654 (3)	0.662257 (15)	0.69368 (3)	0.02274 (10)
Br1	0.57530 (3)	0.644847 (13)	1.13829 (3)	0.03965 (10)
Br2	−0.09274 (3)	0.764024 (13)	0.69082 (3)	0.04195 (10)
Cl1	0.36329 (7)	0.44165 (3)	1.15246 (7)	0.03762 (18)
Cl2	−0.01848 (7)	0.91557 (3)	0.36421 (7)	0.03602 (17)
O1	0.37754 (18)	0.64192 (7)	0.86650 (17)	0.0264 (4)
O2	0.14215 (17)	0.71526 (7)	0.68464 (18)	0.0272 (4)
N1	0.2067 (2)	0.58493 (9)	0.6390 (2)	0.0234 (5)
N2	0.34280 (19)	0.70873 (9)	0.60062 (19)	0.0208 (4)
C1	0.2975 (2)	0.54925 (11)	0.8618 (2)	0.0231 (5)
C2	0.2949 (2)	0.50225 (11)	0.9335 (3)	0.0270 (6)
H2	0.2416	0.4720	0.8913	0.032*
C3	0.3687 (2)	0.49968 (11)	1.0639 (3)	0.0277 (6)
C4	0.4516 (3)	0.54284 (12)	1.1261 (3)	0.0287 (6)
H4	0.5049	0.5406	1.2158	0.034*
C5	0.4548 (3)	0.58833 (11)	1.0562 (2)	0.0259 (6)
C6	0.3753 (2)	0.59526 (10)	0.9230 (2)	0.0225 (5)
C7	0.2230 (2)	0.54617 (11)	0.7227 (3)	0.0254 (5)
H7	0.1819	0.5119	0.6900	0.030*
C8	0.1440 (2)	0.57063 (11)	0.5034 (2)	0.0239 (5)
C9	0.2103 (3)	0.53997 (11)	0.4467 (3)	0.0291 (6)
C10	0.1533 (3)	0.53156 (12)	0.3131 (3)	0.0326 (6)
H10	0.1964	0.5108	0.2726	0.039*
C11	0.0347 (3)	0.55301 (12)	0.2391 (3)	0.0320 (6)
H11	−0.0025	0.5475	0.1481	0.038*
C12	−0.0294 (3)	0.58239 (11)	0.2975 (3)	0.0297 (6)
H12	−0.1105	0.5971	0.2456	0.036*
C13	0.0222 (3)	0.59107 (12)	0.4314 (3)	0.0280 (6)
C14	0.3415 (3)	0.51866 (15)	0.5239 (3)	0.0443 (8)
H14A	0.3946	0.5487	0.5766	0.053*
H14B	0.3773	0.5047	0.4651	0.053*
H14C	0.3382	0.4886	0.5804	0.053*
C15	−0.0532 (3)	0.62008 (16)	0.4928 (3)	0.0455 (8)
H15A	−0.0562	0.5971	0.5626	0.055*
H15B	−0.1394	0.6265	0.4277	0.055*
H15C	−0.0134	0.6556	0.5282	0.055*
C16	0.1773 (2)	0.77951 (10)	0.5396 (2)	0.0210 (5)
C17	0.1093 (2)	0.75899 (10)	0.6102 (2)	0.0208 (5)
C18	0.0010 (2)	0.78977 (11)	0.5987 (3)	0.0247 (5)
C19	−0.0383 (2)	0.83669 (11)	0.5250 (3)	0.0244 (5)
H19	−0.1116	0.8560	0.5198	0.029*
C20	0.0307 (2)	0.85564 (11)	0.4578 (3)	0.0250 (5)
C21	0.1359 (2)	0.82777 (10)	0.4642 (2)	0.0231 (5)
H21	0.1815	0.8412	0.4173	0.028*
C22	0.2909 (2)	0.75423 (11)	0.5415 (2)	0.0221 (5)
H22	0.3315	0.7727	0.4952	0.027*
C23	0.4569 (2)	0.68953 (11)	0.5936 (2)	0.0234 (5)
C24	0.5715 (2)	0.69448 (11)	0.7039 (3)	0.0269 (6)
C25	0.6783 (3)	0.67082 (13)	0.6988 (3)	0.0376 (7)
H25	0.7568	0.6735	0.7721	0.045*
C26	0.6736 (3)	0.64344 (14)	0.5902 (4)	0.0452 (9)
H26	0.7476	0.6267	0.5900	0.054*
C27	0.5609 (3)	0.64060 (13)	0.4820 (3)	0.0405 (8)
H27	0.5586	0.6225	0.4067	0.049*
C28	0.4499 (3)	0.66366 (12)	0.4805 (3)	0.0288 (6)
C29	0.5791 (3)	0.72459 (13)	0.8230 (3)	0.0357 (7)
H29A	0.5418	0.7016	0.8693	0.043*
H29B	0.5325	0.7596	0.7977	0.043*
H29C	0.6678	0.7322	0.8794	0.043*
C30	0.3284 (3)	0.66150 (13)	0.3601 (3)	0.0387 (7)
H30A	0.2577	0.6540	0.3838	0.046*
H30B	0.3336	0.6320	0.3032	0.046*
H30C	0.3148	0.6971	0.3148	0.046*

	U11	U22	U33	U12	U13	U23
Co1	0.02424 (18)	0.02062 (18)	0.02371 (19)	0.00174 (13)	0.01026 (15)	0.00289 (14)
Br1	0.04535 (19)	0.03466 (18)	0.02708 (17)	−0.00775 (13)	0.00302 (14)	−0.00110 (12)
Br2	0.03983 (18)	0.03857 (19)	0.0633 (2)	0.01156 (13)	0.03721 (17)	0.01945 (15)
Cl1	0.0409 (4)	0.0365 (4)	0.0354 (4)	0.0004 (3)	0.0157 (3)	0.0140 (3)
Cl2	0.0365 (4)	0.0288 (4)	0.0433 (4)	0.0091 (3)	0.0170 (3)	0.0161 (3)
O1	0.0289 (10)	0.0226 (10)	0.0251 (10)	0.0012 (7)	0.0084 (8)	0.0037 (8)
O2	0.0294 (10)	0.0232 (10)	0.0340 (10)	0.0063 (7)	0.0182 (8)	0.0091 (8)
N1	0.0228 (11)	0.0236 (11)	0.0233 (11)	−0.0004 (8)	0.0090 (9)	0.0003 (9)
N2	0.0201 (10)	0.0213 (11)	0.0214 (10)	0.0011 (8)	0.0091 (8)	0.0013 (8)
C1	0.0225 (12)	0.0230 (13)	0.0239 (13)	0.0043 (9)	0.0098 (10)	0.0019 (10)
C2	0.0248 (13)	0.0244 (14)	0.0317 (14)	0.0003 (10)	0.0115 (11)	0.0022 (11)
C3	0.0270 (13)	0.0263 (14)	0.0327 (15)	0.0033 (11)	0.0154 (12)	0.0093 (12)
C4	0.0299 (14)	0.0336 (15)	0.0229 (13)	0.0062 (11)	0.0113 (11)	0.0032 (11)
C5	0.0278 (13)	0.0241 (13)	0.0241 (13)	0.0021 (10)	0.0089 (11)	−0.0011 (11)
C6	0.0227 (12)	0.0237 (13)	0.0232 (13)	0.0044 (9)	0.0115 (10)	0.0038 (10)
C7	0.0213 (12)	0.0255 (13)	0.0287 (14)	0.0000 (10)	0.0096 (11)	0.0010 (11)
C8	0.0238 (12)	0.0243 (13)	0.0229 (13)	−0.0013 (10)	0.0091 (11)	0.0014 (10)
C9	0.0307 (14)	0.0244 (14)	0.0301 (15)	0.0008 (11)	0.0105 (12)	−0.0026 (11)
C10	0.0367 (16)	0.0277 (15)	0.0345 (16)	−0.0033 (12)	0.0160 (13)	−0.0094 (12)
C11	0.0378 (16)	0.0294 (15)	0.0218 (13)	−0.0041 (12)	0.0052 (12)	−0.0018 (11)
C12	0.0280 (14)	0.0270 (14)	0.0255 (14)	−0.0005 (11)	0.0022 (11)	−0.0002 (11)
C13	0.0259 (13)	0.0290 (15)	0.0270 (14)	−0.0015 (10)	0.0088 (11)	−0.0016 (11)
C14	0.0354 (17)	0.050 (2)	0.0422 (18)	0.0135 (14)	0.0113 (15)	−0.0085 (16)
C15	0.0268 (15)	0.065 (2)	0.0403 (18)	0.0040 (15)	0.0095 (14)	−0.0139 (17)
C16	0.0206 (12)	0.0188 (12)	0.0225 (12)	−0.0001 (9)	0.0078 (10)	−0.0020 (10)
C17	0.0200 (11)	0.0193 (12)	0.0210 (12)	0.0011 (9)	0.0063 (10)	0.0008 (10)
C18	0.0221 (12)	0.0251 (13)	0.0300 (14)	−0.0015 (10)	0.0139 (11)	0.0014 (11)
C19	0.0199 (12)	0.0235 (13)	0.0275 (14)	0.0032 (9)	0.0076 (10)	0.0008 (11)
C20	0.0257 (13)	0.0215 (13)	0.0248 (13)	0.0018 (10)	0.0075 (11)	0.0038 (10)
C21	0.0225 (12)	0.0228 (13)	0.0227 (13)	−0.0001 (10)	0.0080 (10)	0.0019 (10)
C22	0.0226 (12)	0.0227 (13)	0.0210 (12)	−0.0004 (9)	0.0090 (10)	0.0013 (10)
C23	0.0222 (12)	0.0239 (13)	0.0271 (13)	0.0026 (10)	0.0133 (11)	0.0075 (11)
C24	0.0239 (13)	0.0269 (14)	0.0310 (14)	−0.0002 (10)	0.0123 (11)	0.0118 (11)
C25	0.0246 (14)	0.0439 (18)	0.0441 (18)	0.0050 (12)	0.0140 (13)	0.0217 (15)
C26	0.0390 (18)	0.048 (2)	0.061 (2)	0.0186 (14)	0.0329 (17)	0.0210 (17)
C27	0.057 (2)	0.0370 (18)	0.0435 (18)	0.0131 (15)	0.0372 (17)	0.0081 (14)
C28	0.0340 (15)	0.0265 (14)	0.0303 (15)	0.0056 (11)	0.0178 (12)	0.0062 (11)
C29	0.0310 (15)	0.0383 (17)	0.0314 (16)	−0.0085 (12)	0.0066 (13)	0.0018 (13)
C30	0.0503 (19)	0.0364 (17)	0.0291 (16)	0.0005 (14)	0.0162 (14)	−0.0037 (13)

Co1—O2	1.9006 (18)	C13—C15	1.499 (4)
Co1—O1	1.9144 (18)	C14—H14A	0.9800
Co1—N2	1.983 (2)	C14—H14B	0.9800
Co1—N1	2.000 (2)	C14—H14C	0.9800
Br1—C5	1.901 (3)	C15—H15A	0.9800
Br2—C18	1.898 (3)	C15—H15B	0.9800
Cl1—C3	1.742 (3)	C15—H15C	0.9800
Cl2—C20	1.746 (3)	C16—C21	1.408 (3)
O1—C6	1.302 (3)	C16—C17	1.426 (4)
O2—C17	1.308 (3)	C16—C22	1.445 (3)
N1—C7	1.291 (3)	C17—C18	1.420 (3)
N1—C8	1.447 (3)	C18—C19	1.370 (4)
N2—C22	1.299 (3)	C19—C20	1.392 (4)
N2—C23	1.437 (3)	C19—H19	0.9500
C1—C2	1.405 (4)	C20—C21	1.370 (4)
C1—C6	1.420 (4)	C21—H21	0.9500
C1—C7	1.456 (4)	C22—H22	0.9500
C2—C3	1.372 (4)	C23—C28	1.400 (4)
C2—H2	0.9500	C23—C24	1.406 (4)
C3—C4	1.397 (4)	C24—C25	1.387 (4)
C4—C5	1.365 (4)	C24—C29	1.506 (4)
C4—H4	0.9500	C25—C26	1.381 (5)
C5—C6	1.420 (4)	C25—H25	0.9500
C7—H7	0.9500	C26—C27	1.378 (5)
C8—C13	1.399 (4)	C26—H26	0.9500
C8—C9	1.402 (4)	C27—C28	1.397 (4)
C9—C10	1.397 (4)	C27—H27	0.9500
C9—C14	1.500 (4)	C28—C30	1.506 (4)
C10—C11	1.383 (4)	C29—H29A	0.9800
C10—H10	0.9500	C29—H29B	0.9800
C11—C12	1.381 (4)	C29—H29C	0.9800
C11—H11	0.9500	C30—H30A	0.9800
C12—C13	1.400 (4)	C30—H30B	0.9800
C12—H12	0.9500	C30—H30C	0.9800
O2—Co1—O1	113.77 (8)	H14B—C14—H14C	109.5
O2—Co1—N2	94.94 (8)	C13—C15—H15A	109.5
O1—Co1—N2	115.58 (8)	C13—C15—H15B	109.5
O2—Co1—N1	116.97 (9)	H15A—C15—H15B	109.5
O1—Co1—N1	94.53 (8)	C13—C15—H15C	109.5
N2—Co1—N1	122.51 (9)	H15A—C15—H15C	109.5
C6—O1—Co1	125.79 (17)	H15B—C15—H15C	109.5
C17—O2—Co1	126.25 (17)	C21—C16—C17	120.0 (2)
C7—N1—C8	117.8 (2)	C21—C16—C22	116.1 (2)
C7—N1—Co1	121.47 (18)	C17—C16—C22	123.9 (2)
C8—N1—Co1	120.72 (17)	O2—C17—C18	119.5 (2)
C22—N2—C23	119.1 (2)	O2—C17—C16	124.3 (2)
C22—N2—Co1	122.70 (18)	C18—C17—C16	116.2 (2)
C23—N2—Co1	118.14 (16)	C19—C18—C17	123.2 (2)
C2—C1—C6	120.7 (2)	C19—C18—Br2	119.1 (2)
C2—C1—C7	116.2 (2)	C17—C18—Br2	117.72 (19)
C6—C1—C7	122.9 (2)	C18—C19—C20	119.0 (2)
C3—C2—C1	120.6 (3)	C18—C19—H19	120.5
C3—C2—H2	119.7	C20—C19—H19	120.5
C1—C2—H2	119.7	C21—C20—C19	120.7 (2)
C2—C3—C4	120.3 (2)	C21—C20—Cl2	120.0 (2)
C2—C3—Cl1	120.3 (2)	C19—C20—Cl2	119.2 (2)
C4—C3—Cl1	119.4 (2)	C20—C21—C16	120.8 (2)
C5—C4—C3	119.0 (2)	C20—C21—H21	119.6
C5—C4—H4	120.5	C16—C21—H21	119.6
C3—C4—H4	120.5	N2—C22—C16	126.2 (2)
C4—C5—C6	123.5 (3)	N2—C22—H22	116.9
C4—C5—Br1	119.0 (2)	C16—C22—H22	116.9
C6—C5—Br1	117.4 (2)	C28—C23—C24	122.0 (3)
O1—C6—C5	119.4 (2)	C28—C23—N2	119.3 (2)
O1—C6—C1	125.1 (2)	C24—C23—N2	118.5 (2)
C5—C6—C1	115.6 (2)	C25—C24—C23	117.4 (3)
N1—C7—C1	127.0 (2)	C25—C24—C29	121.0 (3)
N1—C7—H7	116.5	C23—C24—C29	121.6 (3)
C1—C7—H7	116.5	C26—C25—C24	121.9 (3)
C13—C8—C9	122.2 (2)	C26—C25—H25	119.1
C13—C8—N1	118.7 (2)	C24—C25—H25	119.1
C9—C8—N1	119.0 (2)	C27—C26—C25	119.5 (3)
C10—C9—C8	118.1 (2)	C27—C26—H26	120.2
C10—C9—C14	119.8 (3)	C25—C26—H26	120.2
C8—C9—C14	122.0 (2)	C26—C27—C28	121.5 (3)
C11—C10—C9	120.8 (3)	C26—C27—H27	119.2
C11—C10—H10	119.6	C28—C27—H27	119.2
C9—C10—H10	119.6	C27—C28—C23	117.6 (3)
C12—C11—C10	119.9 (3)	C27—C28—C30	120.7 (3)
C12—C11—H11	120.0	C23—C28—C30	121.7 (3)
C10—C11—H11	120.0	C24—C29—H29A	109.5
C11—C12—C13	121.7 (3)	C24—C29—H29B	109.5
C11—C12—H12	119.2	H29A—C29—H29B	109.5
C13—C12—H12	119.2	C24—C29—H29C	109.5
C8—C13—C12	117.2 (3)	H29A—C29—H29C	109.5
C8—C13—C15	122.5 (2)	H29B—C29—H29C	109.5
C12—C13—C15	120.3 (2)	C28—C30—H30A	109.5
C9—C14—H14A	109.5	C28—C30—H30B	109.5
C9—C14—H14B	109.5	H30A—C30—H30B	109.5
H14A—C14—H14B	109.5	C28—C30—H30C	109.5
C9—C14—H14C	109.5	H30A—C30—H30C	109.5
H14A—C14—H14C	109.5	H30B—C30—H30C	109.5
O2—Co1—O1—C6	106.0 (2)	C14—C9—C10—C11	−177.0 (3)
N2—Co1—O1—C6	−145.6 (2)	C9—C10—C11—C12	−1.0 (5)
N1—Co1—O1—C6	−16.2 (2)	C10—C11—C12—C13	−0.3 (4)
O1—Co1—O2—C17	135.3 (2)	C9—C8—C13—C12	−3.5 (4)
N2—Co1—O2—C17	14.5 (2)	N1—C8—C13—C12	172.1 (2)
N1—Co1—O2—C17	−115.9 (2)	C9—C8—C13—C15	175.2 (3)
O2—Co1—N1—C7	−102.8 (2)	N1—C8—C13—C15	−9.2 (4)
O1—Co1—N1—C7	16.8 (2)	C11—C12—C13—C8	2.5 (4)
N2—Co1—N1—C7	141.1 (2)	C11—C12—C13—C15	−176.1 (3)
O2—Co1—N1—C8	77.5 (2)	Co1—O2—C17—C18	169.79 (18)
O1—Co1—N1—C8	−162.86 (19)	Co1—O2—C17—C16	−11.6 (4)
N2—Co1—N1—C8	−38.5 (2)	C21—C16—C17—O2	−178.5 (2)
O2—Co1—N2—C22	−10.4 (2)	C22—C16—C17—O2	0.2 (4)
O1—Co1—N2—C22	−129.8 (2)	C21—C16—C17—C18	0.1 (4)
N1—Co1—N2—C22	116.1 (2)	C22—C16—C17—C18	178.8 (2)
O2—Co1—N2—C23	172.64 (18)	O2—C17—C18—C19	178.6 (2)
O1—Co1—N2—C23	53.3 (2)	C16—C17—C18—C19	−0.1 (4)
N1—Co1—N2—C23	−60.8 (2)	O2—C17—C18—Br2	−1.4 (3)
C6—C1—C2—C3	−0.8 (4)	C16—C17—C18—Br2	179.94 (18)
C7—C1—C2—C3	175.6 (2)	C17—C18—C19—C20	−0.2 (4)
C1—C2—C3—C4	−2.7 (4)	Br2—C18—C19—C20	179.80 (19)
C1—C2—C3—Cl1	179.1 (2)	C18—C19—C20—C21	0.4 (4)
C2—C3—C4—C5	2.2 (4)	C18—C19—C20—Cl2	−179.7 (2)
Cl1—C3—C4—C5	−179.6 (2)	C19—C20—C21—C16	−0.4 (4)
C3—C4—C5—C6	1.9 (4)	Cl2—C20—C21—C16	179.75 (19)
C3—C4—C5—Br1	−175.9 (2)	C17—C16—C21—C20	0.1 (4)
Co1—O1—C6—C5	−173.34 (18)	C22—C16—C21—C20	−178.7 (2)
Co1—O1—C6—C1	6.3 (4)	C23—N2—C22—C16	−179.5 (2)
C4—C5—C6—O1	174.4 (3)	Co1—N2—C22—C16	3.6 (4)
Br1—C5—C6—O1	−7.7 (3)	C21—C16—C22—N2	−177.4 (2)
C4—C5—C6—C1	−5.2 (4)	C17—C16—C22—N2	3.8 (4)
Br1—C5—C6—C1	172.68 (19)	C22—N2—C23—C28	−76.9 (3)
C2—C1—C6—O1	−175.1 (3)	Co1—N2—C23—C28	100.1 (2)
C7—C1—C6—O1	8.8 (4)	C22—N2—C23—C24	106.8 (3)
C2—C1—C6—C5	4.5 (4)	Co1—N2—C23—C24	−76.1 (3)
C7—C1—C6—C5	−171.6 (2)	C28—C23—C24—C25	−2.3 (4)
C8—N1—C7—C1	171.2 (2)	N2—C23—C24—C25	173.9 (2)
Co1—N1—C7—C1	−8.4 (4)	C28—C23—C24—C29	177.2 (3)
C2—C1—C7—N1	176.6 (3)	N2—C23—C24—C29	−6.6 (4)
C6—C1—C7—N1	−7.2 (4)	C23—C24—C25—C26	0.1 (4)
C7—N1—C8—C13	110.2 (3)	C29—C24—C25—C26	−179.4 (3)
Co1—N1—C8—C13	−70.2 (3)	C24—C25—C26—C27	1.8 (5)
C7—N1—C8—C9	−74.1 (3)	C25—C26—C27—C28	−1.6 (5)
Co1—N1—C8—C9	105.6 (3)	C26—C27—C28—C23	−0.5 (5)
C13—C8—C9—C10	2.2 (4)	C26—C27—C28—C30	178.3 (3)
N1—C8—C9—C10	−173.4 (2)	C24—C23—C28—C27	2.5 (4)
C13—C8—C9—C14	179.3 (3)	N2—C23—C28—C27	−173.7 (2)
N1—C8—C9—C14	3.7 (4)	C24—C23—C28—C30	−176.3 (3)
C8—C9—C10—C11	0.1 (4)	N2—C23—C28—C30	7.6 (4)

Table 1

Selected bond lengths (Å)

Co1—O2	1.9006 (18)
Co1—O1	1.9144 (18)
Co1—N2	1.983 (2)
Co1—N1	2.000 (2)