Bis{2,4-dibromo-6-[3-(cyclo­hexyl­amino)­propyl­iminometh­yl]phenolato}cobalt(III) perchlorate

In the title compound, [Co(C₁₆H₂₁Br₂N₂O)₂]ClO₄, a centrosymmetric mononuclear Schiff base cobalt(III) complex, the Co atom is hexa­coordinated by two O and four N atoms from two Schiff base ligands, forming an octa­hedral geometry.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.015 Å
• R factor = 0.075
• wR factor = 0.213
• Data-to-parameter ratio = 19.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         38 Perc.

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.141
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.14
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.69
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.59 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.56 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C14    -   C15     ..       5.50 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C14
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C20
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C30
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C19
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C27
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         15
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H2A    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N4     -   H4A    ...          ?

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.688
            Tmax scaled      0.208 Tmin scaled      0.203
PLAT793_ALERT_1_G Check the Absolute Configuration of N2     = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of N4     = ...          S
PLAT794_ALERT_5_G Check Predicted Bond Valency for Co1         (9)       4.01
PLAT794_ALERT_5_G Check Predicted Bond Valency for Co2         (9)       4.00
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         24

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  16 ALERT level C = Check and explain
   6 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

---

S1. Comment

Cobalt complexes with Schiff base ligands have received much attention in recent years (Sacconi et al., 1965; Zakrzewski & Sacconi, 1968). Some of the complexes have been found to have pharmacological and antitumor properties (Hodnett et al., 1971; Hodnett & Dunn, 1972; Takeuchi et al., 1998). We have recently reported a few transition metal complexes (Diao, Huang et al., 2007; Diao, Shu et al., 2007; Diao, 2007a,b). As an extension of the work on the crystal structures of such complexes, we report herein the crystal structure of the title complex.

The complex is a centrosymmetric mononuclear Schiff base cobalt(III) complex, which consists of a cobalt(III) cation and a perchlorate anion. The Co atom is hexacoordinated by two O and four N atoms from two Schiff base ligands, forming an octahedral geometry (Fig. 1).

Related literature

For related literature, see: Diao (2007a,b); Diao, Huang et al. (2007); Diao, Shu et al. (2007); Hodnett & Dunn (1972); Hodnett et al. (1971); Sacconi et al. (1965); Takeuchi et al. (1998); Zakrzewski & Sacconi (1968).

S2. Experimental

3,5-Dibromosalicylaldehyde (0.2 mmol, 56.0 mg), N-cyclohexyl-1,3-diaminopropane (0.2 mmol, 31.0 mg), and Cu(ClO₄)·7H₂O (0.1 mmol, 39.0 mg) were dissolved in a methanol solution (20 ml). The mixture was stirred for half an hour at room temperature, giving a brown solution. After allowing the solution to stand in air for a week, brown block-like crystals were formed.

S3. Refinement

H atoms were placed in calculated positions and constrained to ride on their parent atoms, with C—H = 0.93–0.97 Å, N—H = 0.91 Å, and with U_iso(H) set at 1.2U_eq(C,N). The ration of observed/unique reflections is low (38%), and the value of R_int is 0.14, due to the poor quality of the diffraction.

Computing details

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

Figures

Fig. 1. Molecular structure of the complex with 30% probabily ellipsoids.

Bis{2,4-dibromo-6-[3-(cyclohexylamino)propyliminomethyl]phenolato}cobalt(III) perchlorate

Crystal data

[Co(C16H21Br2N2O)2]ClO4	F(000) = 1976
Mr = 992.72	Dx = 1.781 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1447 reflections
a = 16.208 (3) Å	θ = 2.3–24.5°
b = 12.801 (3) Å	µ = 4.90 mm^−1
c = 18.060 (4) Å	T = 298 K
β = 98.91 (3)°	Block, brown
V = 3701.8 (14) Å^3	0.33 × 0.32 × 0.32 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	8354 independent reflections
Radiation source: fine-focus sealed tube	3168 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.142
ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −21→21
Tmin = 0.295, Tmax = 0.303	k = −16→16
30784 measured reflections	l = −22→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.213	H-atom parameters constrained
S = 0.96	w = 1/[σ^2(Fo^2) + (0.0821P)^2] where P = (Fo^2 + 2Fc^2)/3
8354 reflections	(Δ/σ)max < 0.001
436 parameters	Δρmax = 1.12 e Å^−3
24 restraints	Δρmin = −0.76 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Co1	0.5000	0.5000	0.5000	0.0388 (4)
Co2	0.0000	0.0000	0.5000	0.0351 (4)
Br1	0.15360 (8)	0.79302 (11)	0.28990 (8)	0.0947 (5)
Br2	0.23554 (7)	0.37506 (9)	0.36766 (7)	0.0779 (4)
Br3	0.40645 (7)	0.02431 (11)	0.36755 (8)	0.0917 (5)
Br4	0.06878 (8)	0.13017 (10)	0.26659 (6)	0.0795 (4)
Cl1	0.35696 (18)	0.8654 (3)	0.67797 (19)	0.0731 (9)
O1	0.3871 (4)	0.4778 (4)	0.4574 (3)	0.0465 (16)
O2	0.0500 (4)	0.0608 (4)	0.4218 (3)	0.0443 (15)
O3	0.3804 (8)	0.8974 (11)	0.6126 (7)	0.175 (5)
O4	0.2889 (8)	0.9120 (11)	0.6912 (7)	0.174 (5)
O5	0.4137 (12)	0.9087 (15)	0.7300 (11)	0.256 (8)
O6	0.3674 (9)	0.7618 (13)	0.6982 (9)	0.206 (6)
N1	0.4761 (5)	0.6429 (6)	0.5224 (4)	0.0442 (19)
N2	0.4722 (5)	0.4576 (6)	0.5999 (4)	0.052 (2)
H2A	0.5201	0.4265	0.6224	0.062*
N3	0.1045 (4)	0.0001 (5)	0.5661 (4)	0.0374 (17)
N4	−0.0236 (4)	0.1438 (6)	0.5369 (4)	0.0453 (19)
H4A	−0.0719	0.1322	0.5553	0.054*
C1	0.3510 (5)	0.6588 (7)	0.4321 (5)	0.044 (2)
C2	0.3363 (6)	0.5496 (8)	0.4234 (5)	0.046 (2)
C3	0.2619 (6)	0.5196 (7)	0.3778 (6)	0.053 (3)
C4	0.2069 (6)	0.5910 (9)	0.3389 (5)	0.059 (3)
H4	0.1574	0.5690	0.3101	0.071*
C5	0.2281 (7)	0.6968 (9)	0.3443 (6)	0.064 (3)
C6	0.2971 (6)	0.7307 (8)	0.3913 (6)	0.054 (3)
H6	0.3083	0.8019	0.3963	0.064*
C7	0.4161 (6)	0.6962 (7)	0.4881 (5)	0.045 (2)
H7	0.4144	0.7666	0.5006	0.054*
C8	0.5282 (6)	0.6920 (8)	0.5894 (5)	0.056 (3)
H8A	0.5066	0.7610	0.5976	0.068*
H8B	0.5851	0.7000	0.5798	0.068*
C9	0.5282 (8)	0.6267 (9)	0.6591 (6)	0.078 (4)
H9A	0.5209	0.6726	0.7003	0.094*
H9B	0.5823	0.5933	0.6715	0.094*
C10	0.4603 (7)	0.5423 (8)	0.6518 (6)	0.070 (3)
H10A	0.4586	0.5125	0.7010	0.084*
H10B	0.4066	0.5749	0.6352	0.084*
C11	0.4077 (6)	0.3707 (7)	0.5978 (5)	0.046 (2)
H11	0.4015	0.3405	0.5474	0.055*
C12	0.4408 (7)	0.2828 (8)	0.6527 (6)	0.071 (3)
H12A	0.4481	0.3086	0.7038	0.085*
H12B	0.4945	0.2585	0.6422	0.085*
C13	0.3771 (9)	0.1920 (8)	0.6434 (7)	0.089 (4)
H13A	0.3740	0.1624	0.5936	0.107*
H13B	0.3958	0.1376	0.6795	0.107*
C14	0.2907 (10)	0.2297 (12)	0.6549 (8)	0.114 (6)
H14A	0.2515	0.1720	0.6475	0.136*
H14B	0.2928	0.2549	0.7058	0.136*
C15	0.2627 (8)	0.3127 (10)	0.6025 (8)	0.090 (4)
H15A	0.2078	0.3356	0.6107	0.108*
H15B	0.2575	0.2854	0.5519	0.108*
C16	0.3215 (6)	0.4068 (8)	0.6094 (7)	0.076 (3)
H16A	0.3007	0.4589	0.5721	0.091*
H16B	0.3242	0.4382	0.6586	0.091*
C17	0.1947 (6)	0.0204 (6)	0.4686 (5)	0.044 (2)
C18	0.1278 (6)	0.0523 (7)	0.4124 (5)	0.045 (2)
C19	0.1514 (6)	0.0796 (7)	0.3438 (5)	0.048 (2)
C20	0.2327 (8)	0.0718 (8)	0.3306 (6)	0.070 (3)
H20	0.2460	0.0901	0.2840	0.084*
C21	0.2949 (6)	0.0365 (8)	0.3870 (7)	0.060 (3)
C22	0.2758 (6)	0.0135 (7)	0.4557 (6)	0.053 (3)
H22	0.3177	−0.0070	0.4942	0.064*
C23	0.1772 (5)	0.0054 (7)	0.5443 (5)	0.045 (2)
H23	0.2233	−0.0012	0.5816	0.054*
C24	0.1034 (6)	0.0094 (7)	0.6471 (5)	0.049 (2)
H24A	0.1603	0.0145	0.6731	0.059*
H24B	0.0785	−0.0530	0.6647	0.059*
C25	0.0551 (7)	0.1031 (8)	0.6650 (5)	0.061 (3)
H25A	0.0881	0.1397	0.7064	0.073*
H25B	0.0048	0.0788	0.6825	0.073*
C26	0.0299 (7)	0.1804 (8)	0.6032 (5)	0.063 (3)
H26A	0.0020	0.2381	0.6237	0.076*
H26B	0.0805	0.2079	0.5879	0.076*
C27	−0.0514 (5)	0.2239 (6)	0.4777 (5)	0.040 (2)
H27	−0.0680	0.1866	0.4303	0.048*
C28	−0.1276 (6)	0.2791 (8)	0.4964 (6)	0.063 (3)
H28A	−0.1133	0.3175	0.5430	0.076*
H28B	−0.1703	0.2283	0.5030	0.076*
C29	−0.1616 (8)	0.3557 (10)	0.4322 (7)	0.095 (4)
H29A	−0.1818	0.3163	0.3871	0.113*
H29B	−0.2081	0.3948	0.4460	0.113*
C30	−0.0944 (10)	0.4309 (10)	0.4163 (8)	0.105 (5)
H30A	−0.1159	0.4736	0.3733	0.126*
H30B	−0.0796	0.4768	0.4590	0.126*
C31	−0.0177 (8)	0.3742 (9)	0.4010 (7)	0.083 (4)
H31A	0.0250	0.4245	0.3938	0.100*
H31B	−0.0311	0.3338	0.3553	0.100*
C32	0.0156 (6)	0.3016 (8)	0.4656 (6)	0.067 (3)
H32A	0.0644	0.2648	0.4542	0.080*
H32B	0.0320	0.3421	0.5109	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0420 (10)	0.0357 (10)	0.0374 (10)	0.0002 (8)	0.0021 (8)	−0.0028 (8)
Co2	0.0375 (9)	0.0342 (9)	0.0329 (10)	0.0023 (7)	0.0031 (7)	−0.0017 (8)
Br1	0.0855 (9)	0.0993 (10)	0.0913 (10)	0.0441 (8)	−0.0112 (8)	0.0101 (8)
Br2	0.0671 (8)	0.0720 (8)	0.0864 (9)	−0.0146 (6)	−0.0138 (6)	−0.0125 (7)
Br3	0.0655 (8)	0.1031 (11)	0.1179 (12)	−0.0095 (7)	0.0496 (8)	−0.0105 (8)
Br4	0.0935 (9)	0.0932 (9)	0.0530 (7)	0.0052 (7)	0.0156 (6)	0.0266 (7)
Cl1	0.0549 (18)	0.088 (2)	0.077 (2)	0.0211 (16)	0.0111 (16)	0.0037 (18)
O1	0.053 (4)	0.039 (4)	0.046 (4)	−0.002 (3)	0.000 (3)	0.000 (3)
O2	0.052 (4)	0.046 (4)	0.036 (4)	0.000 (3)	0.009 (3)	0.005 (3)
O3	0.189 (8)	0.200 (9)	0.152 (8)	0.061 (7)	0.080 (7)	0.013 (7)
O4	0.147 (7)	0.231 (9)	0.156 (8)	0.089 (7)	0.065 (6)	0.045 (7)
O5	0.248 (11)	0.246 (11)	0.256 (11)	−0.018 (9)	−0.018 (9)	−0.007 (9)
O6	0.214 (9)	0.169 (9)	0.239 (10)	−0.003 (8)	0.040 (8)	0.021 (8)
N1	0.042 (5)	0.041 (5)	0.050 (5)	0.002 (4)	0.007 (4)	−0.008 (4)
N2	0.067 (5)	0.040 (5)	0.048 (5)	0.001 (4)	0.008 (4)	0.001 (4)
N3	0.042 (4)	0.032 (4)	0.035 (4)	0.007 (3)	−0.004 (3)	−0.006 (3)
N4	0.048 (5)	0.051 (5)	0.034 (4)	0.005 (4)	−0.001 (4)	−0.007 (4)
C1	0.041 (5)	0.044 (6)	0.047 (6)	0.007 (5)	0.010 (5)	−0.001 (5)
C2	0.049 (6)	0.050 (6)	0.039 (6)	−0.002 (5)	0.008 (5)	−0.004 (5)
C3	0.048 (6)	0.051 (7)	0.059 (7)	−0.002 (5)	0.001 (5)	0.000 (5)
C4	0.046 (6)	0.088 (9)	0.043 (6)	−0.002 (6)	0.000 (5)	−0.013 (6)
C5	0.062 (7)	0.066 (8)	0.062 (8)	0.030 (6)	0.006 (6)	0.014 (6)
C6	0.056 (7)	0.041 (6)	0.065 (7)	0.015 (5)	0.016 (6)	0.002 (5)
C7	0.044 (6)	0.033 (5)	0.060 (7)	−0.001 (5)	0.016 (5)	−0.010 (5)
C8	0.062 (7)	0.052 (7)	0.052 (7)	0.001 (5)	−0.001 (5)	−0.016 (5)
C9	0.105 (10)	0.073 (8)	0.054 (8)	−0.006 (7)	0.002 (7)	−0.022 (6)
C10	0.095 (9)	0.075 (8)	0.045 (7)	−0.012 (7)	0.026 (6)	−0.012 (6)
C11	0.055 (6)	0.045 (6)	0.036 (5)	−0.005 (5)	0.004 (4)	0.014 (5)
C12	0.089 (8)	0.054 (7)	0.064 (7)	−0.015 (6)	−0.004 (6)	0.011 (6)
C13	0.153 (13)	0.038 (7)	0.066 (8)	−0.009 (8)	−0.014 (9)	0.010 (6)
C14	0.141 (14)	0.101 (12)	0.118 (12)	−0.083 (11)	0.078 (11)	−0.030 (10)
C15	0.085 (9)	0.072 (9)	0.119 (12)	−0.022 (7)	0.036 (8)	0.015 (9)
C16	0.052 (7)	0.073 (8)	0.107 (10)	0.011 (6)	0.026 (7)	0.003 (7)
C17	0.056 (6)	0.032 (5)	0.043 (6)	0.003 (4)	0.006 (5)	−0.003 (4)
C18	0.063 (7)	0.028 (5)	0.044 (6)	−0.002 (5)	0.007 (5)	−0.006 (4)
C19	0.065 (7)	0.050 (6)	0.035 (6)	−0.004 (5)	0.019 (5)	0.006 (5)
C20	0.091 (9)	0.069 (8)	0.064 (8)	−0.012 (7)	0.052 (7)	−0.007 (6)
C21	0.046 (6)	0.066 (7)	0.071 (8)	−0.011 (5)	0.018 (6)	−0.002 (6)
C22	0.049 (6)	0.040 (6)	0.072 (8)	−0.008 (5)	0.017 (5)	−0.015 (5)
C23	0.031 (5)	0.042 (6)	0.058 (7)	−0.007 (4)	−0.005 (5)	−0.002 (5)
C24	0.055 (6)	0.053 (6)	0.037 (6)	0.010 (5)	−0.003 (5)	0.003 (5)
C25	0.081 (8)	0.061 (7)	0.036 (6)	0.013 (6)	−0.009 (5)	−0.008 (5)
C26	0.082 (8)	0.054 (7)	0.048 (7)	0.017 (6)	−0.006 (6)	−0.013 (5)
C27	0.051 (6)	0.029 (5)	0.041 (6)	0.001 (4)	0.006 (4)	−0.007 (4)
C28	0.061 (7)	0.067 (7)	0.066 (7)	0.007 (6)	0.023 (6)	−0.011 (6)
C29	0.103 (10)	0.096 (11)	0.084 (10)	0.060 (9)	0.012 (8)	0.005 (8)
C30	0.143 (14)	0.055 (9)	0.112 (12)	0.016 (9)	0.003 (10)	0.040 (8)
C31	0.100 (10)	0.064 (8)	0.082 (9)	−0.022 (7)	0.001 (8)	0.022 (7)
C32	0.070 (8)	0.065 (8)	0.063 (7)	−0.018 (6)	0.006 (6)	0.008 (6)

Geometric parameters (Å, º)

Co1—O1	1.894 (6)	C11—C12	1.541 (12)
Co1—O1^i	1.894 (6)	C11—H11	0.9800
Co1—N1	1.926 (7)	C12—C13	1.546 (14)
Co1—N1^i	1.926 (7)	C12—H12A	0.9700
Co1—N2^i	2.002 (7)	C12—H12B	0.9700
Co1—N2	2.002 (7)	C13—C14	1.526 (17)
Co2—O2^ii	1.900 (6)	C13—H13A	0.9700
Co2—O2	1.900 (6)	C13—H13B	0.9700
Co2—N3^ii	1.915 (7)	C14—C15	1.449 (18)
Co2—N3	1.915 (7)	C14—H14A	0.9700
Co2—N4^ii	2.014 (7)	C14—H14B	0.9700
Co2—N4	2.014 (7)	C15—C16	1.529 (15)
Br1—C5	1.889 (9)	C15—H15A	0.9700
Br2—C3	1.901 (9)	C15—H15B	0.9700
Br3—C21	1.900 (10)	C16—H16A	0.9700
Br4—C19	1.891 (10)	C16—H16B	0.9700
Cl1—O4	1.309 (11)	C17—C22	1.372 (12)
Cl1—O5	1.330 (18)	C17—C18	1.425 (12)
Cl1—O3	1.359 (12)	C17—C23	1.452 (13)
Cl1—O6	1.380 (15)	C18—C19	1.397 (12)
O1—C2	1.319 (10)	C19—C20	1.379 (13)
O2—C18	1.303 (10)	C20—C21	1.394 (14)
N1—C7	1.268 (10)	C20—H20	0.9300
N1—C8	1.503 (11)	C21—C22	1.358 (14)
N2—C10	1.465 (12)	C22—H22	0.9300
N2—C11	1.522 (11)	C23—H23	0.9300
N2—H2A	0.9100	C24—C25	1.495 (12)
N3—C23	1.300 (10)	C24—H24A	0.9700
N3—C24	1.470 (11)	C24—H24B	0.9700
N4—C26	1.443 (11)	C25—C26	1.500 (13)
N4—C27	1.500 (10)	C25—H25A	0.9700
N4—H4A	0.9100	C25—H25B	0.9700
C1—C6	1.397 (12)	C26—H26A	0.9700
C1—C2	1.423 (12)	C26—H26B	0.9700
C1—C7	1.427 (12)	C27—C28	1.507 (12)
C2—C3	1.405 (12)	C27—C32	1.513 (12)
C3—C4	1.389 (13)	C27—H27	0.9800
C4—C5	1.397 (14)	C28—C29	1.553 (14)
C4—H4	0.9300	C28—H28A	0.9700
C5—C6	1.368 (13)	C28—H28B	0.9700
C6—H6	0.9300	C29—C30	1.513 (17)
C7—H7	0.9300	C29—H29A	0.9700
C8—C9	1.510 (14)	C29—H29B	0.9700
C8—H8A	0.9700	C30—C31	1.501 (16)
C8—H8B	0.9700	C30—H30A	0.9700
C9—C10	1.534 (14)	C30—H30B	0.9700
C9—H9A	0.9700	C31—C32	1.523 (14)
C9—H9B	0.9700	C31—H31A	0.9700
C10—H10A	0.9700	C31—H31B	0.9700
C10—H10B	0.9700	C32—H32A	0.9700
C11—C16	1.518 (12)	C32—H32B	0.9700
O1—Co1—O1^i	180.00 (16)	C13—C12—H12A	110.0
O1—Co1—N1	90.8 (3)	C11—C12—H12B	110.0
O1^i—Co1—N1	89.2 (3)	C13—C12—H12B	110.0
O1—Co1—N1^i	89.2 (3)	H12A—C12—H12B	108.4
O1^i—Co1—N1^i	90.8 (3)	C14—C13—C12	111.0 (10)
N1—Co1—N1^i	180.000 (1)	C14—C13—H13A	109.4
O1—Co1—N2^i	90.7 (3)	C12—C13—H13A	109.4
O1^i—Co1—N2^i	89.3 (3)	C14—C13—H13B	109.4
N1—Co1—N2^i	90.7 (3)	C12—C13—H13B	109.4
N1^i—Co1—N2^i	89.3 (3)	H13A—C13—H13B	108.0
O1—Co1—N2	89.3 (3)	C15—C14—C13	110.1 (10)
O1^i—Co1—N2	90.7 (3)	C15—C14—H14A	109.6
N1—Co1—N2	89.3 (3)	C13—C14—H14A	109.6
N1^i—Co1—N2	90.7 (3)	C15—C14—H14B	109.6
N2^i—Co1—N2	180.000 (2)	C13—C14—H14B	109.6
O2^ii—Co2—O2	180.000 (1)	H14A—C14—H14B	108.2
O2^ii—Co2—N3^ii	91.4 (3)	C14—C15—C16	113.4 (11)
O2—Co2—N3^ii	88.6 (3)	C14—C15—H15A	108.9
O2^ii—Co2—N3	88.6 (3)	C16—C15—H15A	108.9
O2—Co2—N3	91.4 (3)	C14—C15—H15B	108.9
N3^ii—Co2—N3	180.000 (1)	C16—C15—H15B	108.9
O2^ii—Co2—N4^ii	89.8 (3)	H15A—C15—H15B	107.7
O2—Co2—N4^ii	90.2 (3)	C11—C16—C15	108.9 (9)
N3^ii—Co2—N4^ii	89.3 (3)	C11—C16—H16A	109.9
N3—Co2—N4^ii	90.7 (3)	C15—C16—H16A	109.9
O2^ii—Co2—N4	90.2 (3)	C11—C16—H16B	109.9
O2—Co2—N4	89.8 (3)	C15—C16—H16B	109.9
N3^ii—Co2—N4	90.7 (3)	H16A—C16—H16B	108.3
N3—Co2—N4	89.3 (3)	C22—C17—C18	122.8 (9)
N4^ii—Co2—N4	180.0 (4)	C22—C17—C23	118.9 (9)
O4—Cl1—O5	101.0 (11)	C18—C17—C23	118.0 (8)
O4—Cl1—O3	112.3 (8)	O2—C18—C19	119.9 (9)
O5—Cl1—O3	103.5 (11)	O2—C18—C17	125.2 (8)
O4—Cl1—O6	117.5 (9)	C19—C18—C17	114.9 (9)
O5—Cl1—O6	99.8 (10)	C20—C19—C18	122.4 (10)
O3—Cl1—O6	118.8 (9)	C20—C19—Br4	118.9 (8)
C2—O1—Co1	125.3 (6)	C18—C19—Br4	118.7 (8)
C18—O2—Co2	126.5 (6)	C19—C20—C21	120.0 (9)
C7—N1—C8	117.5 (8)	C19—C20—H20	120.0
C7—N1—Co1	124.9 (6)	C21—C20—H20	120.0
C8—N1—Co1	117.4 (6)	C22—C21—C20	119.8 (10)
C10—N2—C11	113.5 (8)	C22—C21—Br3	120.6 (9)
C10—N2—Co1	116.5 (6)	C20—C21—Br3	119.6 (9)
C11—N2—Co1	115.1 (5)	C21—C22—C17	120.1 (10)
C10—N2—H2A	103.1	C21—C22—H22	120.0
C11—N2—H2A	103.1	C17—C22—H22	120.0
Co1—N2—H2A	103.1	N3—C23—C17	127.7 (8)
C23—N3—C24	116.7 (7)	N3—C23—H23	116.2
C23—N3—Co2	124.5 (6)	C17—C23—H23	116.2
C24—N3—Co2	118.3 (6)	N3—C24—C25	111.6 (7)
C26—N4—C27	116.5 (7)	N3—C24—H24A	109.3
C26—N4—Co2	116.8 (6)	C25—C24—H24A	109.3
C27—N4—Co2	116.1 (5)	N3—C24—H24B	109.3
C26—N4—H4A	101.0	C25—C24—H24B	109.3
C27—N4—H4A	101.0	H24A—C24—H24B	108.0
Co2—N4—H4A	101.0	C24—C25—C26	117.3 (8)
C6—C1—C2	120.6 (9)	C24—C25—H25A	108.0
C6—C1—C7	119.0 (9)	C26—C25—H25A	108.0
C2—C1—C7	120.0 (8)	C24—C25—H25B	108.0
O1—C2—C3	120.0 (8)	C26—C25—H25B	108.0
O1—C2—C1	123.5 (8)	H25A—C25—H25B	107.2
C3—C2—C1	116.5 (9)	N4—C26—C25	117.6 (8)
C4—C3—C2	122.9 (9)	N4—C26—H26A	107.9
C4—C3—Br2	118.3 (8)	C25—C26—H26A	107.9
C2—C3—Br2	118.8 (7)	N4—C26—H26B	107.9
C3—C4—C5	118.1 (9)	C25—C26—H26B	107.9
C3—C4—H4	120.9	H26A—C26—H26B	107.2
C5—C4—H4	120.9	N4—C27—C28	109.1 (7)
C6—C5—C4	121.3 (9)	N4—C27—C32	114.1 (7)
C6—C5—Br1	120.8 (9)	C28—C27—C32	110.8 (8)
C4—C5—Br1	117.8 (8)	N4—C27—H27	107.5
C5—C6—C1	120.2 (9)	C28—C27—H27	107.5
C5—C6—H6	119.9	C32—C27—H27	107.5
C1—C6—H6	119.9	C27—C28—C29	109.7 (8)
N1—C7—C1	126.4 (8)	C27—C28—H28A	109.7
N1—C7—H7	116.8	C29—C28—H28A	109.7
C1—C7—H7	116.8	C27—C28—H28B	109.7
N1—C8—C9	111.5 (8)	C29—C28—H28B	109.7
N1—C8—H8A	109.3	H28A—C28—H28B	108.2
C9—C8—H8A	109.3	C30—C29—C28	111.1 (10)
N1—C8—H8B	109.3	C30—C29—H29A	109.4
C9—C8—H8B	109.3	C28—C29—H29A	109.4
H8A—C8—H8B	108.0	C30—C29—H29B	109.4
C8—C9—C10	114.3 (9)	C28—C29—H29B	109.4
C8—C9—H9A	108.7	H29A—C29—H29B	108.0
C10—C9—H9A	108.7	C31—C30—C29	111.6 (10)
C8—C9—H9B	108.7	C31—C30—H30A	109.3
C10—C9—H9B	108.7	C29—C30—H30A	109.3
H9A—C9—H9B	107.6	C31—C30—H30B	109.3
N2—C10—C9	114.3 (9)	C29—C30—H30B	109.3
N2—C10—H10A	108.7	H30A—C30—H30B	108.0
C9—C10—H10A	108.7	C30—C31—C32	111.1 (10)
N2—C10—H10B	108.7	C30—C31—H31A	109.4
C9—C10—H10B	108.7	C32—C31—H31A	109.4
H10A—C10—H10B	107.6	C30—C31—H31B	109.4
C16—C11—N2	114.7 (8)	C32—C31—H31B	109.4
C16—C11—C12	111.7 (8)	H31A—C31—H31B	108.0
N2—C11—C12	110.4 (7)	C27—C32—C31	109.5 (8)
C16—C11—H11	106.5	C27—C32—H32A	109.8
N2—C11—H11	106.5	C31—C32—H32A	109.8
C12—C11—H11	106.5	C27—C32—H32B	109.8
C11—C12—C13	108.6 (8)	C31—C32—H32B	109.8
C11—C12—H12A	110.0	H32A—C32—H32B	108.2

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y, −z+1.