trans-Bis{2,4-dichloro-6-[(3-cyclo­hexyl­amino­propyl­imino)meth­yl]phenolato}cobalt(III) perchlorate

The title compound, [Co(C₁₆H₂₁Cl₂N₂O)₂]ClO₄, possesses two independent half-mol­ecules of the cation in the asymmetric unit. The symmetry of both cations is C_i. The Co^III atoms are six-coordinated by four N and two O atoms from two Schiff bases, forming slightly distorted octa­hedral coordination environments.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in solvent or counterion
• R factor = 0.073
• wR factor = 0.160
• Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.63 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.61 Ratio
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        Cl5
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      44.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT420_ALERT_2_C D-H Without Acceptor       N4     -   H4     ...          ?
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl4    ..  O5'     ..       3.02 Ang.

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

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

---

S1. Comment

Schiff base complexes are very important in coordination chemistry because of their easy preparation, interesting structures and excellent properties (Chang et al., 1998; Chaturvedl, 1977; Archer & Wang, 1990; Costamagna et al., 1992; Bhatia et al., 1981). In order to investigate the crystal structures of such complexes, a new cobalt(III) complex, (I), is reported here.

Compound (I) is a perchlorate salt of discrete mononuclear cobalt(III) complex cations (Fig. 1). The structure is similar to that recently reported for the cobalt(III) complex containing the 3-[(3-cyclohexylaminopropylimino)methyl]naphthalen-2-olate ligand (Li et al., 2004). The are two independent half-molecules of the cation in the asymmetric unit. The symmetry of both cations is C_i. Both Co^III atoms are in a slightly distorted octahedral geometry provided by two O and four N atoms from two Schiff bases. The bond lengths and angles involving the Co atoms are the same (within experimental error) in each molecule (Table 1) and are comparable to those of the complex previously cited. As expected, the cyclohexyl groups adopt a chair conformations to minimize the steric effects. The unique ClO₄⁻ anion is disordered over two sites with occupancies 0.581 (2):0.419 (2). The crystal packing is shown in Fig. 2.

S2. Experimental

3,5-Dichlorosalicylaldehyde (0.1 mmol, 19.1 mg) and N-cyclohexyl-1,3-diaminopropane (0.1 mmol, 15.6 mg) were dissolved in MeOH (10 ml). The mixture was stirred for 15 min to give a clear yellow solution, then a MeOH solution of Co(ClO₄)₃·7H₂O (0.1 mmol, 48.3 mg) was added. The mixture was stirred at room temperature for 15 min and filtered. The filtrate was kept in air for 3 d, and brown block-shaped crystals were formed at the bottom of the vessel on slow evaporation of the solvent.

S3. Refinement

Atoms H2 and H4 were located in a difference Fourier map and refined isotropically, with N—H distances restrained to 0.90 (1) Å and U_iso = 0.08 Ų. All other H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å, and with U_iso(H) = 1.2U_eq(C). The O atoms of the perchlorate anion are disordered over two distinct sites with occupancies of 0.581 (2) and 0.419 (2). The Cl—O and O···O distances in both disordered components were restrained to be equal.

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The structure of one of the independent cations of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are not shown.
	Fig. 2. The crystal packing of (I), viewed along the b axis. The minor components of the disordered perchlorate anions and H atoms have been omitted.

(I)

Crystal data

[Co(C16H21Cl2N2O)2]·ClO4	F(000) = 1688
Mr = 814.88	Dx = 1.501 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6581 reflections
a = 16.136 (2) Å	θ = 2.2–25.2°
b = 12.752 (2) Å	µ = 0.90 mm^−1
c = 17.771 (2) Å	T = 298 K
β = 99.486 (1)°	Block, brown
V = 3606.7 (8) Å^3	0.35 × 0.17 × 0.13 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	8227 independent reflections
Radiation source: fine-focus sealed tube	6373 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
ω scan	θmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→20
Tmin = 0.745, Tmax = 0.893	k = −16→16
30380 measured reflections	l = −23→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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ^2(Fo^2) + (0.0524P)^2 + 4.3537P] where P = (Fo^2 + 2Fc^2)/3
8227 reflections	(Δ/σ)max < 0.001
479 parameters	Δρmax = 0.56 e Å^−3
44 restraints	Δρmin = −0.38 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	Occ. (<1)
Co1	0.5000	0.5000	0.5000	0.03075 (16)
Co2	0.0000	1.0000	0.5000	0.03254 (17)
Cl1	0.26386 (8)	0.89156 (11)	0.63441 (8)	0.0788 (4)
Cl2	0.34603 (10)	1.29238 (14)	0.70003 (9)	0.0995 (6)
Cl3	0.43179 (10)	0.62425 (12)	0.73226 (7)	0.0821 (4)
Cl4	0.10614 (10)	0.53039 (15)	0.63682 (11)	0.1060 (6)
Cl5	0.14237 (8)	0.36283 (11)	0.32176 (8)	0.0682 (3)
O1	0.11362 (16)	0.98064 (18)	0.54379 (14)	0.0398 (6)
O2	0.45250 (16)	0.5593 (2)	0.58013 (13)	0.0391 (6)
O3	0.1297 (9)	0.2565 (6)	0.3122 (8)	0.152 (6)	0.581 (13)
O4	0.0955 (9)	0.4111 (10)	0.2609 (7)	0.199 (9)	0.581 (13)
O5	0.1252 (7)	0.3949 (10)	0.3904 (5)	0.128 (6)	0.581 (13)
O6	0.2270 (5)	0.3794 (12)	0.3196 (6)	0.148 (7)	0.581 (13)
O3'	0.1837 (7)	0.4467 (8)	0.2953 (6)	0.085 (4)	0.419 (13)
O4'	0.1857 (11)	0.3234 (13)	0.3880 (9)	0.173 (9)	0.419 (13)
O5'	0.0665 (9)	0.4022 (10)	0.3370 (14)	0.184 (12)	0.419 (13)
O6'	0.1234 (12)	0.2846 (14)	0.2692 (10)	0.213 (16)	0.419 (13)
N1	0.02139 (19)	1.1435 (2)	0.47560 (17)	0.0382 (7)
N2	0.0271 (2)	0.9563 (3)	0.39813 (17)	0.0420 (7)
N3	0.39328 (19)	0.5043 (2)	0.43304 (16)	0.0357 (6)
N4	0.5239 (2)	0.6442 (2)	0.46371 (17)	0.0412 (7)
C1	0.1640 (2)	1.0530 (3)	0.57701 (19)	0.0374 (8)
C2	0.2397 (3)	1.0241 (3)	0.6233 (2)	0.0489 (10)
C3	0.2946 (3)	1.0970 (4)	0.6610 (2)	0.0596 (13)
H3	0.3439	1.0757	0.6919	0.072*
C4	0.2751 (3)	1.2016 (4)	0.6523 (2)	0.0594 (13)
C5	0.2056 (3)	1.2348 (4)	0.6058 (2)	0.0546 (11)
H5	0.1948	1.3062	0.5993	0.066*
C6	0.1497 (2)	1.1611 (3)	0.5671 (2)	0.0417 (9)
C7	0.0821 (2)	1.1986 (3)	0.5095 (2)	0.0427 (9)
H7	0.0832	1.2690	0.4961	0.051*
C8	−0.0328 (3)	1.1904 (3)	0.4090 (2)	0.0507 (10)
H8A	−0.0131	1.2604	0.4002	0.061*
H8B	−0.0899	1.1959	0.4192	0.061*
C9	−0.0317 (3)	1.1232 (4)	0.3383 (2)	0.0593 (12)
H9A	−0.0853	1.0876	0.3261	0.071*
H9B	−0.0262	1.1691	0.2959	0.071*
C10	0.0363 (3)	1.0433 (4)	0.3452 (2)	0.0562 (11)
H10A	0.0380	1.0142	0.2950	0.067*
H10B	0.0896	1.0778	0.3622	0.067*
C11	0.0934 (2)	0.8711 (3)	0.4020 (2)	0.0403 (8)
H11	0.1007	0.8420	0.4537	0.048*
C12	0.1785 (3)	0.9098 (4)	0.3898 (3)	0.0631 (12)
H12A	0.1974	0.9651	0.4261	0.076*
H12B	0.1745	0.9387	0.3388	0.076*
C13	0.2413 (3)	0.8205 (5)	0.3999 (4)	0.0901 (19)
H13A	0.2951	0.8455	0.3894	0.108*
H13B	0.2492	0.7962	0.4523	0.108*
C14	0.2119 (4)	0.7316 (5)	0.3475 (4)	0.098 (2)
H14A	0.2522	0.6747	0.3565	0.118*
H14B	0.2089	0.7545	0.2951	0.118*
C15	0.1272 (4)	0.6926 (4)	0.3592 (3)	0.0782 (17)
H15A	0.1310	0.6641	0.4103	0.094*
H15B	0.1090	0.6369	0.3231	0.094*
C16	0.0623 (3)	0.7825 (3)	0.3481 (3)	0.0585 (12)
H16A	0.0546	0.8072	0.2958	0.070*
H16B	0.0085	0.7574	0.3586	0.070*
C17	0.3748 (2)	0.5528 (3)	0.5899 (2)	0.0409 (9)
C18	0.3525 (3)	0.5803 (3)	0.6611 (3)	0.0553 (11)
C19	0.2714 (4)	0.5732 (4)	0.6745 (3)	0.0707 (15)
H19	0.2590	0.5908	0.7222	0.085*
C20	0.2084 (3)	0.5400 (4)	0.6176 (3)	0.0673 (14)
C21	0.2252 (3)	0.5164 (3)	0.5472 (3)	0.0555 (11)
H21	0.1818	0.4966	0.5087	0.067*
C22	0.3080 (2)	0.5217 (3)	0.5322 (2)	0.0419 (9)
C23	0.3215 (2)	0.5092 (3)	0.4553 (2)	0.0409 (8)
H23	0.2740	0.5041	0.4179	0.049*
C24	0.3943 (3)	0.5118 (3)	0.3505 (2)	0.0432 (9)
H24A	0.3372	0.5170	0.3233	0.052*
H24B	0.4195	0.4490	0.3333	0.052*
C25	0.4443 (3)	0.6076 (4)	0.3330 (2)	0.0546 (11)
H25A	0.4958	0.5838	0.3172	0.065*
H25B	0.4120	0.6446	0.2903	0.065*
C26	0.4662 (3)	0.6825 (3)	0.3969 (2)	0.0552 (11)
H26A	0.4910	0.7441	0.3777	0.066*
H26B	0.4146	0.7046	0.4136	0.066*
C27	0.5510 (2)	0.7249 (3)	0.5255 (2)	0.0371 (8)
H27	0.5676	0.6860	0.5732	0.044*
C28	0.6282 (3)	0.7827 (4)	0.5100 (3)	0.0611 (12)
H28A	0.6147	0.8225	0.4631	0.073*
H28B	0.6719	0.7327	0.5038	0.073*
C29	0.6599 (4)	0.8566 (5)	0.5758 (3)	0.0831 (17)
H29A	0.6804	0.8157	0.6211	0.100*
H29B	0.7065	0.8975	0.5633	0.100*
C30	0.5916 (5)	0.9298 (4)	0.5923 (4)	0.097 (2)
H30A	0.6126	0.9715	0.6371	0.117*
H30B	0.5765	0.9772	0.5496	0.117*
C31	0.5148 (4)	0.8706 (4)	0.6058 (3)	0.0826 (17)
H31A	0.4711	0.9200	0.6131	0.099*
H31B	0.5283	0.8290	0.6518	0.099*
C32	0.4826 (3)	0.7989 (3)	0.5387 (3)	0.0563 (11)
H32A	0.4344	0.7595	0.5494	0.068*
H32B	0.4649	0.8406	0.4932	0.068*
H2	−0.0222 (17)	0.927 (4)	0.377 (3)	0.080*
H4	0.570 (2)	0.634 (4)	0.442 (3)	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0352 (3)	0.0304 (3)	0.0268 (3)	−0.0033 (3)	0.0056 (3)	0.0014 (3)
Co2	0.0376 (4)	0.0286 (3)	0.0297 (3)	−0.0012 (3)	0.0004 (3)	0.0030 (3)
Cl1	0.0605 (7)	0.0767 (9)	0.0889 (9)	0.0122 (6)	−0.0182 (7)	0.0182 (7)
Cl2	0.0873 (10)	0.1170 (13)	0.0863 (10)	−0.0608 (10)	−0.0087 (8)	−0.0174 (9)
Cl3	0.1070 (11)	0.0937 (10)	0.0501 (7)	−0.0106 (8)	0.0261 (7)	−0.0272 (7)
Cl4	0.0724 (9)	0.1263 (14)	0.1361 (15)	0.0153 (9)	0.0673 (10)	0.0199 (11)
Cl5	0.0534 (7)	0.0792 (9)	0.0698 (8)	−0.0222 (6)	0.0035 (6)	0.0070 (7)
O1	0.0427 (14)	0.0320 (13)	0.0411 (14)	0.0007 (11)	−0.0039 (11)	0.0009 (11)
O2	0.0448 (15)	0.0417 (15)	0.0327 (13)	−0.0040 (12)	0.0118 (11)	−0.0027 (11)
O3	0.181 (12)	0.056 (6)	0.217 (16)	−0.010 (6)	0.030 (12)	0.012 (7)
O4	0.237 (18)	0.176 (12)	0.140 (11)	0.073 (12)	−0.100 (11)	0.015 (9)
O5	0.129 (10)	0.186 (13)	0.079 (6)	−0.077 (10)	0.048 (6)	−0.011 (7)
O6	0.086 (7)	0.253 (16)	0.111 (8)	−0.096 (9)	0.037 (6)	−0.079 (10)
O3'	0.057 (7)	0.124 (9)	0.076 (7)	−0.012 (6)	0.017 (5)	0.029 (6)
O4'	0.147 (15)	0.140 (14)	0.205 (18)	0.020 (11)	−0.046 (14)	0.066 (13)
O5'	0.108 (12)	0.125 (12)	0.36 (3)	0.027 (10)	0.153 (17)	0.036 (18)
O6'	0.163 (18)	0.33 (4)	0.152 (18)	−0.15 (2)	0.031 (14)	−0.13 (2)
N1	0.0463 (18)	0.0300 (16)	0.0375 (16)	0.0009 (13)	0.0045 (14)	0.0056 (13)
N2	0.052 (2)	0.0385 (17)	0.0341 (17)	0.0014 (15)	0.0040 (14)	0.0014 (14)
N3	0.0423 (17)	0.0337 (15)	0.0305 (15)	−0.0044 (13)	0.0045 (12)	0.0023 (12)
N4	0.056 (2)	0.0319 (16)	0.0345 (16)	−0.0073 (15)	0.0054 (14)	0.0044 (13)
C1	0.0390 (19)	0.044 (2)	0.0294 (18)	−0.0041 (16)	0.0075 (15)	0.0037 (15)
C2	0.043 (2)	0.062 (3)	0.041 (2)	−0.0052 (19)	0.0035 (17)	0.0095 (19)
C3	0.042 (2)	0.097 (4)	0.037 (2)	−0.016 (2)	−0.0037 (18)	0.011 (2)
C4	0.055 (3)	0.075 (3)	0.045 (2)	−0.036 (2)	0.003 (2)	−0.002 (2)
C5	0.057 (3)	0.056 (3)	0.052 (2)	−0.023 (2)	0.012 (2)	−0.002 (2)
C6	0.043 (2)	0.045 (2)	0.038 (2)	−0.0131 (17)	0.0090 (16)	0.0001 (17)
C7	0.053 (2)	0.0293 (18)	0.048 (2)	−0.0059 (17)	0.0145 (18)	0.0028 (16)
C8	0.059 (3)	0.039 (2)	0.051 (2)	0.0027 (19)	0.001 (2)	0.0154 (18)
C9	0.073 (3)	0.060 (3)	0.042 (2)	0.008 (2)	0.001 (2)	0.019 (2)
C10	0.071 (3)	0.061 (3)	0.038 (2)	0.009 (2)	0.013 (2)	0.011 (2)
C11	0.046 (2)	0.039 (2)	0.0349 (19)	0.0037 (17)	0.0032 (16)	−0.0003 (16)
C12	0.051 (3)	0.064 (3)	0.077 (3)	−0.002 (2)	0.014 (2)	0.004 (3)
C13	0.060 (3)	0.089 (4)	0.126 (5)	0.020 (3)	0.031 (3)	0.010 (4)
C14	0.128 (6)	0.078 (4)	0.099 (5)	0.063 (4)	0.051 (4)	0.023 (4)
C15	0.125 (5)	0.046 (3)	0.057 (3)	0.020 (3)	−0.002 (3)	−0.003 (2)
C16	0.077 (3)	0.045 (2)	0.048 (2)	0.000 (2)	−0.007 (2)	−0.0096 (19)
C17	0.052 (2)	0.033 (2)	0.042 (2)	0.0013 (17)	0.0189 (18)	0.0030 (16)
C18	0.072 (3)	0.048 (2)	0.051 (3)	0.001 (2)	0.026 (2)	−0.003 (2)
C19	0.089 (4)	0.065 (3)	0.072 (3)	0.010 (3)	0.052 (3)	0.000 (3)
C20	0.059 (3)	0.069 (3)	0.086 (4)	0.014 (2)	0.045 (3)	0.017 (3)
C21	0.046 (2)	0.054 (3)	0.070 (3)	0.0085 (19)	0.019 (2)	0.014 (2)
C22	0.041 (2)	0.036 (2)	0.051 (2)	0.0034 (16)	0.0152 (17)	0.0069 (17)
C23	0.0375 (19)	0.038 (2)	0.045 (2)	−0.0031 (16)	0.0017 (16)	0.0092 (17)
C24	0.047 (2)	0.050 (2)	0.0300 (18)	−0.0049 (18)	−0.0005 (16)	0.0024 (16)
C25	0.069 (3)	0.058 (3)	0.035 (2)	−0.017 (2)	0.0005 (19)	0.0093 (19)
C26	0.075 (3)	0.044 (2)	0.041 (2)	−0.007 (2)	−0.007 (2)	0.0138 (18)
C27	0.044 (2)	0.0310 (18)	0.0362 (19)	−0.0025 (15)	0.0058 (16)	−0.0013 (15)
C28	0.063 (3)	0.056 (3)	0.066 (3)	−0.020 (2)	0.013 (2)	0.000 (2)
C29	0.078 (4)	0.078 (4)	0.089 (4)	−0.044 (3)	0.004 (3)	−0.014 (3)
C30	0.144 (6)	0.043 (3)	0.094 (4)	−0.013 (4)	−0.013 (4)	−0.019 (3)
C31	0.101 (4)	0.060 (3)	0.083 (4)	0.023 (3)	0.002 (3)	−0.028 (3)
C32	0.059 (3)	0.046 (2)	0.061 (3)	0.011 (2)	0.000 (2)	−0.007 (2)

Geometric parameters (Å, º)

Co1—O2^i	1.883 (2)	C10—H10B	0.9700
Co1—O2	1.883 (2)	C11—C12	1.509 (6)
Co1—N3^i	1.926 (3)	C11—C16	1.512 (5)
Co1—N3	1.926 (3)	C11—H11	0.9800
Co1—N4^i	2.007 (3)	C12—C13	1.515 (7)
Co1—N4	2.007 (3)	C12—H12A	0.9700
Co2—O1	1.886 (2)	C12—H12B	0.9700
Co2—O1^ii	1.886 (2)	C13—C14	1.493 (9)
Co2—N1	1.924 (3)	C13—H13A	0.9700
Co2—N1^ii	1.924 (3)	C13—H13B	0.9700
Co2—N2	2.010 (3)	C14—C15	1.501 (8)
Co2—N2^ii	2.010 (3)	C14—H14A	0.9700
Cl1—C2	1.739 (5)	C14—H14B	0.9700
Cl2—C4	1.746 (4)	C15—C16	1.543 (6)
Cl3—C18	1.738 (5)	C15—H15A	0.9700
Cl4—C20	1.743 (5)	C15—H15B	0.9700
Cl5—O5	1.357 (7)	C16—H16A	0.9700
Cl5—O4	1.361 (7)	C16—H16B	0.9700
Cl5—O4'	1.363 (9)	C17—C18	1.416 (5)
Cl5—O6'	1.367 (9)	C17—C22	1.416 (6)
Cl5—O3	1.377 (7)	C18—C19	1.370 (6)
Cl5—O3'	1.384 (8)	C19—C20	1.378 (8)
Cl5—O6	1.388 (7)	C19—H19	0.9300
Cl5—O5'	1.390 (8)	C20—C21	1.357 (7)
O1—C1	1.304 (4)	C21—C22	1.406 (5)
O2—C17	1.296 (4)	C21—H21	0.9300
N1—C7	1.274 (5)	C22—C23	1.429 (5)
N1—C8	1.478 (5)	C23—H23	0.9300
N2—C10	1.479 (5)	C24—C25	1.523 (5)
N2—C11	1.518 (5)	C24—H24A	0.9700
N2—H2	0.90 (4)	C24—H24B	0.9700
N3—C23	1.286 (5)	C25—C26	1.482 (6)
N3—C24	1.472 (4)	C25—H25A	0.9700
N4—C26	1.466 (5)	C25—H25B	0.9700
N4—C27	1.517 (5)	C26—H26A	0.9700
N4—H4	0.90 (4)	C26—H26B	0.9700
C1—C2	1.404 (5)	C27—C32	1.500 (5)
C1—C6	1.405 (5)	C27—C28	1.512 (5)
C2—C3	1.379 (6)	C27—H27	0.9800
C3—C4	1.372 (7)	C28—C29	1.523 (7)
C3—H3	0.9300	C28—H28A	0.9700
C4—C5	1.348 (6)	C28—H28B	0.9700
C5—C6	1.403 (5)	C29—C30	1.509 (8)
C5—H5	0.9300	C29—H29A	0.9700
C6—C7	1.447 (5)	C29—H29B	0.9700
C7—H7	0.9300	C30—C31	1.503 (9)
C8—C9	1.523 (6)	C30—H30A	0.9700
C8—H8A	0.9700	C30—H30B	0.9700
C8—H8B	0.9700	C31—C32	1.524 (6)
C9—C10	1.487 (6)	C31—H31A	0.9700
C9—H9A	0.9700	C31—H31B	0.9700
C9—H9B	0.9700	C32—H32A	0.9700
C10—H10A	0.9700	C32—H32B	0.9700
O2^i—Co1—O2	180.0	C9—C10—H10B	108.6
O2^i—Co1—N3^i	91.26 (12)	H10A—C10—H10B	107.6
O2—Co1—N3^i	88.74 (12)	C12—C11—C16	111.7 (4)
O2^i—Co1—N3	88.74 (12)	C12—C11—N2	114.3 (3)
O2—Co1—N3	91.26 (12)	C16—C11—N2	110.4 (3)
N3^i—Co1—N3	180.0	C12—C11—H11	106.7
O2^i—Co1—N4^i	89.93 (12)	C16—C11—H11	106.7
O2—Co1—N4^i	90.07 (12)	N2—C11—H11	106.7
N3^i—Co1—N4^i	88.58 (13)	C11—C12—C13	110.1 (4)
N3—Co1—N4^i	91.42 (13)	C11—C12—H12A	109.6
O2^i—Co1—N4	90.07 (12)	C13—C12—H12A	109.6
O2—Co1—N4	89.93 (12)	C11—C12—H12B	109.6
N3^i—Co1—N4	91.42 (13)	C13—C12—H12B	109.6
N3—Co1—N4	88.58 (13)	H12A—C12—H12B	108.2
N4^i—Co1—N4	180.0	C14—C13—C12	111.0 (5)
O1—Co2—O1^ii	180.0	C14—C13—H13A	109.4
O1—Co2—N1	91.10 (12)	C12—C13—H13A	109.4
O1^ii—Co2—N1	88.90 (12)	C14—C13—H13B	109.4
O1—Co2—N1^ii	88.90 (12)	C12—C13—H13B	109.4
O1^ii—Co2—N1^ii	91.10 (12)	H13A—C13—H13B	108.0
N1—Co2—N1^ii	180.0	C13—C14—C15	111.7 (5)
O1—Co2—N2	89.69 (12)	C13—C14—H14A	109.3
O1^ii—Co2—N2	90.31 (12)	C15—C14—H14A	109.3
N1—Co2—N2	89.27 (13)	C13—C14—H14B	109.3
N1^ii—Co2—N2	90.73 (13)	C15—C14—H14B	109.3
O1—Co2—N2^ii	90.31 (12)	H14A—C14—H14B	107.9
O1^ii—Co2—N2^ii	89.69 (12)	C14—C15—C16	110.5 (4)
N1—Co2—N2^ii	90.73 (13)	C14—C15—H15A	109.5
N1^ii—Co2—N2^ii	89.27 (13)	C16—C15—H15A	109.5
N2—Co2—N2^ii	180.0	C14—C15—H15B	109.5
O5—Cl5—O4	114.2 (7)	C16—C15—H15B	109.5
O5—Cl5—O4'	59.1 (8)	H15A—C15—H15B	108.1
O4—Cl5—O4'	173.1 (9)	C11—C16—C15	109.1 (4)
O5—Cl5—O6'	141.1 (8)	C11—C16—H16A	109.9
O4—Cl5—O6'	75.8 (10)	C15—C16—H16A	109.9
O4'—Cl5—O6'	110.3 (8)	C11—C16—H16B	109.9
O5—Cl5—O3	111.1 (6)	C15—C16—H16B	109.9
O4—Cl5—O3	107.2 (7)	H16A—C16—H16B	108.3
O4'—Cl5—O3	77.8 (8)	O2—C17—C18	119.9 (4)
O5—Cl5—O3'	104.7 (6)	O2—C17—C22	124.0 (3)
O4—Cl5—O3'	67.4 (7)	C18—C17—C22	116.1 (4)
O4'—Cl5—O3'	111.8 (7)	C19—C18—C17	122.0 (5)
O6'—Cl5—O3'	113.5 (8)	C19—C18—Cl3	120.3 (4)
O3—Cl5—O3'	142.1 (7)	C17—C18—Cl3	117.7 (3)
O5—Cl5—O6	109.0 (5)	C18—C19—C20	120.2 (4)
O4—Cl5—O6	109.2 (7)	C18—C19—H19	119.9
O4'—Cl5—O6	73.4 (8)	C20—C19—H19	119.9
O6'—Cl5—O6	101.7 (9)	C21—C20—C19	120.6 (4)
O3—Cl5—O6	105.9 (7)	C21—C20—Cl4	120.3 (5)
O3'—Cl5—O6	48.8 (6)	C19—C20—Cl4	119.1 (4)
O5—Cl5—O5'	53.1 (8)	C20—C21—C22	120.3 (5)
O4—Cl5—O5'	66.4 (9)	C20—C21—H21	119.8
O4'—Cl5—O5'	107.9 (8)	C22—C21—H21	119.8
O6'—Cl5—O5'	107.0 (8)	C21—C22—C17	120.7 (4)
O3—Cl5—O5'	105.2 (9)	C21—C22—C23	118.4 (4)
O3'—Cl5—O5'	106.0 (6)	C17—C22—C23	120.4 (3)
O6—Cl5—O5'	148.4 (9)	N3—C23—C22	125.9 (4)
C1—O1—Co2	125.8 (2)	N3—C23—H23	117.0
C17—O2—Co1	126.7 (2)	C22—C23—H23	117.0
C7—N1—C8	117.6 (3)	N3—C24—C25	110.5 (3)
C7—N1—Co2	124.8 (3)	N3—C24—H24A	109.6
C8—N1—Co2	117.5 (2)	C25—C24—H24A	109.6
C10—N2—C11	114.9 (3)	N3—C24—H24B	109.6
C10—N2—Co2	115.1 (3)	C25—C24—H24B	109.6
C11—N2—Co2	114.5 (2)	H24A—C24—H24B	108.1
C10—N2—H2	103 (3)	C26—C25—C24	115.3 (3)
C11—N2—H2	107 (3)	C26—C25—H25A	108.4
Co2—N2—H2	101 (3)	C24—C25—H25A	108.4
C23—N3—C24	117.5 (3)	C26—C25—H25B	108.4
C23—N3—Co1	124.8 (3)	C24—C25—H25B	108.4
C24—N3—Co1	117.5 (2)	H25A—C25—H25B	107.5
C26—N4—C27	115.4 (3)	N4—C26—C25	116.4 (4)
C26—N4—Co1	115.8 (2)	N4—C26—H26A	108.2
C27—N4—Co1	115.9 (2)	C25—C26—H26A	108.2
C26—N4—H4	99 (3)	N4—C26—H26B	108.2
C27—N4—H4	105 (3)	C25—C26—H26B	108.2
Co1—N4—H4	103 (3)	H26A—C26—H26B	107.3
O1—C1—C2	119.8 (4)	C32—C27—C28	111.8 (4)
O1—C1—C6	124.1 (3)	C32—C27—N4	114.1 (3)
C2—C1—C6	116.1 (4)	C28—C27—N4	110.3 (3)
C3—C2—C1	122.3 (4)	C32—C27—H27	106.7
C3—C2—Cl1	119.1 (3)	C28—C27—H27	106.7
C1—C2—Cl1	118.6 (3)	N4—C27—H27	106.7
C4—C3—C2	118.9 (4)	C27—C28—C29	110.1 (4)
C4—C3—H3	120.5	C27—C28—H28A	109.6
C2—C3—H3	120.5	C29—C28—H28A	109.6
C5—C4—C3	121.8 (4)	C27—C28—H28B	109.6
C5—C4—Cl2	120.1 (4)	C29—C28—H28B	109.6
C3—C4—Cl2	118.1 (4)	H28A—C28—H28B	108.2
C4—C5—C6	119.5 (4)	C30—C29—C28	111.6 (5)
C4—C5—H5	120.2	C30—C29—H29A	109.3
C6—C5—H5	120.2	C28—C29—H29A	109.3
C5—C6—C1	121.1 (4)	C30—C29—H29B	109.3
C5—C6—C7	118.3 (4)	C28—C29—H29B	109.3
C1—C6—C7	120.1 (3)	H29A—C29—H29B	108.0
N1—C7—C6	125.7 (3)	C31—C30—C29	111.6 (4)
N1—C7—H7	117.2	C31—C30—H30A	109.3
C6—C7—H7	117.2	C29—C30—H30A	109.3
N1—C8—C9	110.3 (3)	C31—C30—H30B	109.3
N1—C8—H8A	109.6	C29—C30—H30B	109.3
C9—C8—H8A	109.6	H30A—C30—H30B	108.0
N1—C8—H8B	109.6	C30—C31—C32	111.2 (5)
C9—C8—H8B	109.6	C30—C31—H31A	109.4
H8A—C8—H8B	108.1	C32—C31—H31A	109.4
C10—C9—C8	115.3 (4)	C30—C31—H31B	109.4
C10—C9—H9A	108.5	C32—C31—H31B	109.4
C8—C9—H9A	108.5	H31A—C31—H31B	108.0
C10—C9—H9B	108.5	C27—C32—C31	109.5 (4)
C8—C9—H9B	108.5	C27—C32—H32A	109.8
H9A—C9—H9B	107.5	C31—C32—H32A	109.8
N2—C10—C9	114.6 (4)	C27—C32—H32B	109.8
N2—C10—H10A	108.6	C31—C32—H32B	109.8
C9—C10—H10A	108.6	H32A—C32—H32B	108.2
N2—C10—H10B	108.6

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4^iii	0.90 (4)	2.55 (4)	3.223 (8)	132 (4)

Symmetry code: (iii) −x, y+1/2, −z+1/2.