[(–)-(1S,2S)-N,N′-Bis(2-oxidobenzyl­idene)-1,2-diphenyl­ethane-1,2-diamine]­bis­(pyridine)cobalt(III) perchlorate methanol hemisolvate hemihydrate

In the title compound, [Co(C₂₈H₂₂N₂O₂)(C₅H₅N)₂]ClO₄·0.5CH₄O·0.5H₂O, each Co^III ion is coordinated by the tetra­dentate N,N′-bis­(2-oxidobenzyl­idene)-1,2-diphenyl­ethane-1,2-diamine ligand [Co—N = 1.900 (3) and 1.903 (3) Å; Co—O = 1.885 (3) and 1.891 (3) Å] and two pyridine ligands [Co—N = 1.967 (4) and 1.977 (3) Å] in a distorted octa­hedral geometry. The packing of the cations and anions forms voids of 258 ų, which are filled by methanol and solvent water mol­ecules with half occupancies. O—H...O hydrogen bonds between solvent molecules, perchlorate anions and water molecules, and between water molecules and O atoms of the ligand, help to consolidate the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in solvent or counterion
• R factor = 0.050
• wR factor = 0.145
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C25    --  C26     ..       5.22 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C26    --  C27     ..       5.98 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C31
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ......       2.80 Sigma
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.99
           From the CIF: _reflns_number_total               7407
           Count of symmetry unique reflns         4152
           Completeness (_total/calc)            178.40%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3255
           Fraction of Friedel pairs measured     0.784
           Are heavy atom types Z>Si present        yes
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         13
PLAT302_ALERT_4_G Anion/Solvent Disorder .........................      19.00 Perc.
PLAT791_ALERT_4_G Confirm the Absolute Configuration of C15    ...          S
PLAT791_ALERT_4_G Confirm the Absolute Configuration of C16    ...          S

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

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

---

S1. Comment

The cobalt complexes with tetradentate Schiff base ligands have been extensively studied due to their important utilities in mimic cobalamin (B₁₂) coenzymes (Amirnasr et al., 2001; Cmi et al., 1998; Polson et al., 1997), and as dioxygen carriers and oxygen activators (Yamada, 1999; Henson et al., 1999) . In addition, Co^III Schiff base complexes have also been used as antimicrobial agents when their two axial positions are occupied by two amine ligands (Botteher et al., 1997). Herein, we report the new Co^III complex based on the chiral tetradentate Schiff base ligand (-)-(1S,2S)-N,N'-Bis(salicylidene)-1,2- diphenyl-1,2-ethanediamine (L), whose structure has been reported recently (Korendovych & Rybak-Akimova, 2003).

In the cation (Fig. 1), the coordination sphere of Co^III ion is a distorted octahedron, in which four equational positions come from two N atoms and two O atoms of the tetradentate Schiff base ligand and the apical positions are occupied by N atoms of two pyridine molecules. The bond lengths of Co—O(L) and Co—N(L) are 1.885 (3), 1.891 (3)A% and 1.900 (3), 1.903 (3)A%, respectively, which are in agreement with the corresponding bond lengths in the similar Co^III Schiff base complex trans-[Co(salen)(py)₂][BPh₄] (Shi et al., 1995)). The distances of Co—N_py 1.967 (4) and 1.977 (3)A% are also consistent with those distances in the same complex, but slightly longer than the distances of Co—N_{Schiff base}.

Related literature

For related crystal structures, see: Korendovych & Rybak-Akimova (2003); Shi et al. (1995). For general background, see: Amirnasr et al. (2001); Botteher et al., 1997; Cmi et al. (1998); Henson et al. (1999); Polson et al. (1997); Yamada (1999); Zhang et al. (1990).

S2. Experimental

The free Schiff base ligand L was synthesized according to the literature (Zhang et al., 1990). The synthsis of the title complex was carried out by reacting CoClO₄.6H₂O, pyridine and L (molar ratio 1:2:1 in methanol. After the stirring process was continued for about 30 min at room temperature, the mixture was filtered and the filtrate was allowed to partial evaporate in air for several days to produce crystals suitable for X-ray diffraction. Anal. Calcd for C_38.5H₃₅ClCoN₄O₇: C, 60.84; H, 4.64; N, 7.37. Found: C, 60.64; H, 4.65; N, 7.39.

S3. Refinement

The occupancies of methanol (O7, C39) and crystalline water (O8) molecules were set to 0.5 and not refined. The common U_iso was refined for O7 and C39 atoms (methanol). Atom O8 was also refined isotropically. All H atoms were placed in idealized positions (C—H 0.93-0.98 Å; O-H 0.82-0.85 Å), and refined as riding with U_iso(H) = 1.2-1.5U_eq of the parent atom.

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 1998); software used to prepare material for publication: XP (Sheldrick, 1998).

Figures

Fig. 1. A view of the cation of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms omited for clarity.

[(-)-(1S,2S)-N,N'-Bis(2-oxidobenzylidene)- 1,2-diphenylethane-1,2-diamine] bis(pyridine)cobalt(III) perchlorate methanol hemisolvate hemihydrate

Crystal data

[Co(C28H22N2O2)(C5H5N)2]ClO4·0.5CH4O·0.5H2O	Dx = 1.334 Mg m^−3 Dm = 1.334 Mg m^−3 Dm measured by not measured
Mr = 760.09	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 8558 reflections
a = 10.8900 (3) Å	θ = 2.4–20.8°
b = 18.6219 (5) Å	µ = 0.58 mm^−1
c = 18.6557 (6) Å	T = 273 K
V = 3783.24 (19) Å^3	Block, red-brown
Z = 4	0.18 × 0.16 × 0.14 mm
F(000) = 1576

Data collection

Bruker APEXII CCD area-detector diffractometer	7407 independent reflections
Radiation source: fine-focus sealed tube	5476 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
ϕ and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −13→13
Tmin = 0.903, Tmax = 0.924	k = −22→22
42911 measured reflections	l = −23→23

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.050	w = 1/[σ^2(Fo^2) + (0.0885P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.145	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.48 e Å^−3
7407 reflections	Δρmin = −0.37 e Å^−3
463 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
13 restraints	Extinction coefficient: 0.0014 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 3248 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.03 (2)

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	0.50476 (4)	0.57650 (2)	0.75640 (2)	0.04751 (16)
Cl1	0.10093 (14)	0.50610 (10)	0.55336 (8)	0.1022 (5)
O1	0.6076 (3)	0.65694 (14)	0.76901 (15)	0.0568 (7)
O2	0.5983 (3)	0.55521 (14)	0.67367 (15)	0.0619 (7)
O3	0.1244 (5)	0.5541 (3)	0.4915 (2)	0.1324 (18)
O4	0.2142 (4)	0.4859 (3)	0.5844 (3)	0.1202 (15)
O5	0.0367 (5)	0.4459 (4)	0.5318 (4)	0.175 (3)
O6	0.0303 (5)	0.5444 (3)	0.6048 (3)	0.1398 (18)
O7	0.6798 (12)	0.6643 (6)	0.5737 (6)	0.153 (4)*	0.50
H7	0.6495	0.6359	0.6022	0.230*	0.50
O8	0.9347 (13)	0.6770 (6)	0.5559 (7)	0.163 (4)*	0.50
H8C	0.8572	0.6746	0.5606	0.195*	0.50
H8D	0.9657	0.6377	0.5703	0.195*	0.50
N1	0.4061 (3)	0.59406 (15)	0.83873 (17)	0.0460 (7)
N2	0.3989 (3)	0.49659 (15)	0.74280 (16)	0.0462 (7)
N3	0.6234 (3)	0.52046 (17)	0.81394 (17)	0.0506 (8)
N4	0.4010 (4)	0.63945 (18)	0.6973 (2)	0.0601 (9)
C1	0.5455 (4)	0.68095 (18)	0.8912 (2)	0.0498 (9)
C2	0.6202 (4)	0.69134 (19)	0.8297 (2)	0.0497 (9)
C3	0.7149 (4)	0.7448 (2)	0.8337 (3)	0.0571 (10)
H3	0.7637	0.7540	0.7938	0.069*
C4	0.7341 (4)	0.7824 (2)	0.8957 (3)	0.0607 (11)
H4	0.7955	0.8171	0.8973	0.073*
C5	0.6637 (4)	0.7697 (2)	0.9561 (3)	0.0632 (11)
H5	0.6799	0.7947	0.9982	0.076*
C6	0.5700 (4)	0.7204 (2)	0.9542 (2)	0.0578 (10)
H6	0.5222	0.7129	0.9948	0.069*
C7	0.4382 (4)	0.63562 (19)	0.8909 (2)	0.0477 (9)
H7A	0.3883	0.6364	0.9313	0.057*
C8	0.5417 (3)	0.4304 (2)	0.6702 (2)	0.0482 (8)
C9	0.5718 (4)	0.3609 (2)	0.6450 (2)	0.0578 (10)
H9	0.5178	0.3231	0.6536	0.069*
C10	0.6775 (4)	0.3479 (2)	0.6087 (3)	0.0666 (12)
H10	0.6975	0.3016	0.5941	0.080*
C11	0.7546 (4)	0.4046 (3)	0.5938 (3)	0.0729 (13)
H11	0.8273	0.3959	0.5692	0.087*
C12	0.7280 (4)	0.4727 (3)	0.6140 (3)	0.0688 (12)
H12	0.7809	0.5098	0.6013	0.083*
C13	0.6209 (4)	0.4882 (2)	0.6542 (2)	0.0539 (10)
C14	0.4274 (3)	0.4402 (2)	0.7069 (2)	0.0493 (9)
H14	0.3701	0.4033	0.7045	0.059*
C15	0.2981 (3)	0.5456 (2)	0.8473 (2)	0.0473 (9)
H15	0.3202	0.5088	0.8826	0.057*
C16	0.2763 (3)	0.5075 (2)	0.7757 (2)	0.0486 (9)
H16	0.2305	0.5406	0.7448	0.058*
C17	0.1814 (3)	0.5823 (2)	0.8738 (2)	0.0510 (9)
C18	0.1280 (4)	0.6393 (3)	0.8389 (3)	0.0713 (12)
H18	0.1664	0.6588	0.7989	0.086*
C19	0.0192 (4)	0.6679 (3)	0.8621 (3)	0.0758 (13)
H19	−0.0159	0.7057	0.8367	0.091*
C20	−0.0378 (4)	0.6424 (2)	0.9208 (3)	0.0686 (12)
H20	−0.1112	0.6629	0.9361	0.082*
C21	0.0128 (4)	0.5855 (2)	0.9584 (2)	0.0649 (11)
H21	−0.0263	0.5672	0.9988	0.078*
C22	0.1243 (4)	0.5560 (2)	0.9345 (2)	0.0536 (9)
H22	0.1601	0.5183	0.9598	0.064*
C23	0.1990 (4)	0.4396 (2)	0.7842 (2)	0.0571 (10)
C24	0.2292 (6)	0.3877 (3)	0.8359 (3)	0.0832 (15)
H24	0.2987	0.3929	0.8644	0.100*
C25	0.1518 (7)	0.3278 (3)	0.8433 (4)	0.105 (2)
H25	0.1708	0.2934	0.8776	0.126*
C26	0.0507 (6)	0.3185 (4)	0.8023 (4)	0.1008 (18)
H26	0.0012	0.2783	0.8083	0.121*
C27	0.0227 (5)	0.3690 (4)	0.7522 (4)	0.1023 (19)
H27	−0.0467	0.3632	0.7237	0.123*
C28	0.0970 (4)	0.4298 (3)	0.7429 (3)	0.0739 (12)
H28	0.0765	0.4637	0.7084	0.089*
C29	0.5918 (4)	0.4749 (2)	0.8660 (3)	0.0630 (11)
H29	0.5086	0.4681	0.8749	0.076*
C30	0.6749 (5)	0.4372 (3)	0.9074 (3)	0.0778 (13)
H30	0.6486	0.4067	0.9437	0.093*
C31	0.7970 (5)	0.4464 (4)	0.8932 (4)	0.0970 (19)
H31	0.8562	0.4212	0.9188	0.116*
C32	0.8306 (4)	0.4940 (3)	0.8399 (4)	0.0849 (16)
H32	0.9133	0.5017	0.8301	0.102*
C33	0.7431 (4)	0.5298 (2)	0.8013 (3)	0.0631 (11)
H33	0.7675	0.5615	0.7654	0.076*
C34	0.3626 (6)	0.6221 (3)	0.6330 (3)	0.0879 (17)
H34	0.3810	0.5764	0.6160	0.105*
C35	0.2964 (7)	0.6674 (3)	0.5888 (4)	0.114 (3)
H35	0.2703	0.6521	0.5438	0.137*
C36	0.2701 (7)	0.7351 (4)	0.6125 (4)	0.117 (2)
H36	0.2287	0.7672	0.5829	0.140*
C37	0.3057 (6)	0.7558 (3)	0.6813 (4)	0.0915 (17)
H37	0.2856	0.8008	0.6996	0.110*
C38	0.3721 (5)	0.7068 (2)	0.7213 (3)	0.0691 (12)
H38	0.3985	0.7203	0.7668	0.083*
C39	0.5940 (19)	0.7285 (10)	0.5644 (10)	0.153 (4)*	0.50
H39A	0.5563	0.7398	0.6095	0.230*	0.50
H39B	0.5316	0.7170	0.5299	0.230*	0.50
H39C	0.6403	0.7692	0.5479	0.230*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0420 (3)	0.0414 (3)	0.0591 (3)	−0.0055 (2)	0.0071 (3)	−0.0055 (2)
Cl1	0.0737 (9)	0.1434 (14)	0.0895 (9)	−0.0270 (9)	0.0163 (7)	−0.0380 (9)
O1	0.0533 (16)	0.0459 (14)	0.0712 (18)	−0.0099 (12)	0.0084 (14)	−0.0100 (12)
O2	0.0624 (17)	0.0527 (16)	0.0705 (17)	−0.0156 (14)	0.0165 (15)	−0.0143 (13)
O3	0.125 (4)	0.198 (5)	0.073 (2)	−0.016 (4)	0.013 (2)	−0.008 (3)
O4	0.073 (3)	0.155 (4)	0.132 (3)	−0.013 (3)	0.003 (3)	−0.009 (3)
O5	0.109 (4)	0.213 (6)	0.204 (6)	−0.068 (4)	0.018 (4)	−0.090 (5)
O6	0.141 (4)	0.157 (4)	0.121 (3)	0.013 (4)	0.047 (3)	−0.035 (3)
N1	0.0350 (15)	0.0403 (16)	0.0626 (18)	0.0018 (13)	0.0020 (14)	−0.0051 (14)
N2	0.0385 (15)	0.0437 (16)	0.0564 (17)	−0.0024 (13)	0.0045 (15)	−0.0035 (14)
N3	0.0392 (17)	0.0451 (17)	0.068 (2)	−0.0015 (14)	−0.0004 (15)	−0.0106 (15)
N4	0.060 (2)	0.0524 (19)	0.068 (2)	−0.0124 (18)	−0.0020 (19)	0.0029 (16)
C1	0.044 (2)	0.0363 (19)	0.070 (2)	0.0064 (16)	−0.0002 (18)	−0.0026 (17)
C2	0.041 (2)	0.0355 (19)	0.073 (3)	0.0044 (16)	−0.0035 (19)	−0.0068 (18)
C3	0.044 (2)	0.047 (2)	0.081 (3)	0.0023 (18)	−0.003 (2)	−0.003 (2)
C4	0.047 (2)	0.040 (2)	0.096 (3)	0.0008 (18)	−0.018 (2)	−0.010 (2)
C5	0.054 (3)	0.053 (2)	0.083 (3)	0.002 (2)	−0.016 (2)	−0.014 (2)
C6	0.057 (3)	0.046 (2)	0.070 (3)	0.0029 (19)	−0.009 (2)	−0.0085 (19)
C7	0.046 (2)	0.0396 (18)	0.058 (2)	0.0036 (17)	0.0047 (18)	−0.0028 (17)
C8	0.0429 (19)	0.0465 (19)	0.0552 (19)	−0.0043 (17)	0.0000 (15)	−0.0079 (18)
C9	0.050 (2)	0.052 (2)	0.071 (3)	−0.0026 (19)	0.002 (2)	−0.0113 (19)
C10	0.052 (2)	0.062 (3)	0.086 (3)	0.003 (2)	0.004 (2)	−0.017 (2)
C11	0.046 (3)	0.082 (3)	0.091 (3)	−0.001 (2)	0.014 (2)	−0.027 (3)
C12	0.050 (2)	0.074 (3)	0.082 (3)	−0.015 (2)	0.018 (2)	−0.015 (2)
C13	0.049 (2)	0.055 (2)	0.057 (2)	−0.0091 (19)	0.0057 (18)	−0.0100 (18)
C14	0.045 (2)	0.043 (2)	0.060 (2)	−0.0073 (17)	0.0032 (18)	−0.0049 (17)
C15	0.039 (2)	0.045 (2)	0.058 (2)	0.0004 (16)	0.0063 (17)	0.0015 (17)
C16	0.0388 (18)	0.045 (2)	0.062 (2)	−0.0017 (17)	0.0045 (16)	−0.0038 (17)
C17	0.0359 (18)	0.052 (2)	0.065 (2)	0.0015 (17)	0.0010 (17)	−0.0017 (19)
C18	0.059 (3)	0.070 (3)	0.085 (3)	0.015 (2)	0.010 (2)	0.009 (2)
C19	0.054 (3)	0.075 (3)	0.098 (3)	0.027 (2)	0.008 (3)	0.006 (2)
C20	0.049 (2)	0.068 (3)	0.089 (3)	0.011 (2)	0.004 (2)	−0.014 (2)
C21	0.047 (2)	0.081 (3)	0.066 (2)	−0.004 (2)	0.009 (2)	−0.013 (2)
C22	0.047 (2)	0.056 (2)	0.059 (2)	0.0006 (18)	0.0067 (18)	−0.0029 (17)
C23	0.049 (2)	0.056 (2)	0.066 (2)	−0.0120 (19)	0.0161 (19)	−0.009 (2)
C24	0.095 (4)	0.062 (3)	0.092 (3)	−0.030 (3)	−0.003 (3)	0.005 (3)
C25	0.130 (5)	0.074 (3)	0.112 (4)	−0.036 (4)	0.028 (4)	0.002 (3)
C26	0.089 (4)	0.098 (4)	0.116 (4)	−0.045 (3)	0.030 (3)	−0.027 (3)
C27	0.052 (3)	0.113 (4)	0.141 (5)	−0.031 (3)	0.016 (4)	−0.054 (4)
C28	0.049 (2)	0.081 (3)	0.092 (3)	−0.012 (2)	0.004 (2)	−0.021 (3)
C29	0.046 (2)	0.058 (2)	0.086 (3)	0.007 (2)	−0.001 (2)	−0.003 (2)
C30	0.070 (3)	0.064 (3)	0.099 (3)	0.008 (3)	−0.015 (3)	0.008 (3)
C31	0.068 (4)	0.096 (4)	0.127 (5)	0.030 (3)	−0.036 (4)	−0.020 (4)
C32	0.045 (2)	0.087 (4)	0.123 (4)	0.010 (3)	−0.011 (3)	−0.034 (4)
C33	0.040 (2)	0.067 (3)	0.082 (3)	−0.003 (2)	0.003 (2)	−0.022 (2)
C34	0.111 (5)	0.067 (3)	0.085 (4)	−0.016 (3)	−0.021 (3)	0.007 (3)
C35	0.154 (7)	0.075 (4)	0.114 (5)	−0.020 (4)	−0.063 (5)	0.025 (3)
C36	0.137 (6)	0.082 (4)	0.131 (6)	−0.004 (4)	−0.045 (5)	0.036 (4)
C37	0.103 (4)	0.058 (3)	0.113 (4)	0.004 (3)	−0.013 (4)	0.015 (3)
C38	0.069 (3)	0.059 (3)	0.079 (3)	−0.002 (2)	−0.002 (2)	0.006 (2)

Geometric parameters (Å, º)

Co1—O1	1.885 (3)	C15—C17	1.525 (5)
Co1—O2	1.891 (3)	C15—C16	1.530 (5)
Co1—N2	1.900 (3)	C15—H15	0.9800
Co1—N1	1.903 (3)	C16—C23	1.528 (5)
Co1—N4	1.967 (4)	C16—H16	0.9800
Co1—N3	1.977 (3)	C17—C18	1.374 (6)
Cl1—O5	1.381 (5)	C17—C22	1.383 (5)
Cl1—O4	1.414 (5)	C18—C19	1.368 (6)
Cl1—O6	1.421 (5)	C18—H18	0.9300
Cl1—O3	1.482 (5)	C19—C20	1.347 (7)
O1—C2	1.309 (5)	C19—H19	0.9300
O2—C13	1.322 (5)	C20—C21	1.385 (6)
O7—C39	1.53 (2)	C20—H20	0.9300
O7—H7	0.8200	C21—C22	1.407 (5)
O8—H8C	0.8501	C21—H21	0.9300
O8—H8D	0.8501	C22—H22	0.9300
N1—C7	1.291 (5)	C23—C28	1.364 (6)
N1—C15	1.492 (5)	C23—C24	1.403 (7)
N2—C14	1.284 (4)	C24—C25	1.405 (7)
N2—C16	1.483 (5)	C24—H24	0.9300
N3—C29	1.334 (6)	C25—C26	1.351 (9)
N3—C33	1.337 (5)	C25—H25	0.9300
N4—C34	1.310 (6)	C26—C27	1.362 (10)
N4—C38	1.369 (6)	C26—H26	0.9300
C1—C6	1.411 (6)	C27—C28	1.401 (7)
C1—C2	1.420 (6)	C27—H27	0.9300
C1—C7	1.441 (5)	C28—H28	0.9300
C2—C3	1.436 (6)	C29—C30	1.381 (6)
C3—C4	1.367 (6)	C29—H29	0.9300
C3—H3	0.9300	C30—C31	1.367 (8)
C4—C5	1.383 (7)	C30—H30	0.9300
C4—H4	0.9300	C31—C32	1.381 (8)
C5—C6	1.373 (6)	C31—H31	0.9300
C5—H5	0.9300	C32—C33	1.368 (7)
C6—H6	0.9300	C32—H32	0.9300
C7—H7A	0.9300	C33—H33	0.9300
C8—C13	1.412 (5)	C34—C35	1.382 (8)
C8—C9	1.416 (6)	C34—H34	0.9300
C8—C14	1.431 (5)	C35—C36	1.366 (10)
C9—C10	1.357 (6)	C35—H35	0.9300
C9—H9	0.9300	C36—C37	1.396 (10)
C10—C11	1.378 (7)	C36—H36	0.9300
C10—H10	0.9300	C37—C38	1.382 (7)
C11—C12	1.354 (7)	C37—H37	0.9300
C11—H11	0.9300	C38—H38	0.9300
C12—C13	1.416 (6)	C39—H39A	0.9600
C12—H12	0.9300	C39—H39B	0.9600
C14—H14	0.9300	C39—H39C	0.9600
O1—Co1—O2	87.05 (11)	N1—C15—H15	107.5
O1—Co1—N2	178.89 (13)	C17—C15—H15	107.5
O2—Co1—N2	93.08 (12)	C16—C15—H15	107.5
O1—Co1—N1	95.62 (12)	N2—C16—C23	115.1 (3)
O2—Co1—N1	177.32 (12)	N2—C16—C15	106.6 (3)
N2—Co1—N1	84.24 (13)	C23—C16—C15	112.3 (3)
O1—Co1—N4	86.43 (14)	N2—C16—H16	107.5
O2—Co1—N4	88.66 (15)	C23—C16—H16	107.5
N2—Co1—N4	92.48 (14)	C15—C16—H16	107.5
N1—Co1—N4	91.49 (14)	C18—C17—C22	118.1 (4)
O1—Co1—N3	87.91 (13)	C18—C17—C15	123.1 (4)
O2—Co1—N3	88.89 (14)	C22—C17—C15	118.7 (3)
N2—Co1—N3	93.19 (12)	C19—C18—C17	121.2 (5)
N1—Co1—N3	91.22 (13)	C19—C18—H18	119.4
N4—Co1—N3	173.94 (14)	C17—C18—H18	119.4
O5—Cl1—O4	110.2 (4)	C20—C19—C18	121.2 (5)
O5—Cl1—O6	109.3 (3)	C20—C19—H19	119.4
O4—Cl1—O6	109.2 (3)	C18—C19—H19	119.4
O5—Cl1—O3	110.5 (4)	C19—C20—C21	119.9 (4)
O4—Cl1—O3	109.2 (3)	C19—C20—H20	120.0
O6—Cl1—O3	108.4 (3)	C21—C20—H20	120.0
C2—O1—Co1	124.0 (3)	C20—C21—C22	118.8 (4)
C13—O2—Co1	121.5 (2)	C20—C21—H21	120.6
C39—O7—H7	109.5	C22—C21—H21	120.6
H8C—O8—H8D	108.3	C17—C22—C21	120.6 (4)
C7—N1—C15	119.7 (3)	C17—C22—H22	119.7
C7—N1—Co1	123.9 (3)	C21—C22—H22	119.7
C15—N1—Co1	115.3 (2)	C28—C23—C24	119.1 (4)
C14—N2—C16	123.1 (3)	C28—C23—C16	120.1 (4)
C14—N2—Co1	124.3 (2)	C24—C23—C16	120.7 (4)
C16—N2—Co1	112.6 (2)	C23—C24—C25	118.2 (5)
C29—N3—C33	117.6 (4)	C23—C24—H24	120.9
C29—N3—Co1	124.2 (3)	C25—C24—H24	120.9
C33—N3—Co1	118.2 (3)	C26—C25—C24	122.4 (6)
C34—N4—C38	116.9 (4)	C26—C25—H25	118.8
C34—N4—Co1	123.4 (3)	C24—C25—H25	118.8
C38—N4—Co1	119.6 (3)	C25—C26—C27	118.8 (6)
C6—C1—C2	119.6 (4)	C25—C26—H26	120.6
C6—C1—C7	117.5 (4)	C27—C26—H26	120.6
C2—C1—C7	122.7 (3)	C26—C27—C28	120.9 (6)
O1—C2—C1	124.9 (3)	C26—C27—H27	119.5
O1—C2—C3	117.4 (4)	C28—C27—H27	119.5
C1—C2—C3	117.6 (4)	C23—C28—C27	120.5 (5)
C4—C3—C2	120.6 (4)	C23—C28—H28	119.7
C4—C3—H3	119.7	C27—C28—H28	119.7
C2—C3—H3	119.7	N3—C29—C30	124.1 (4)
C3—C4—C5	121.1 (4)	N3—C29—H29	117.9
C3—C4—H4	119.5	C30—C29—H29	117.9
C5—C4—H4	119.5	C31—C30—C29	117.7 (5)
C6—C5—C4	120.4 (4)	C31—C30—H30	121.1
C6—C5—H5	119.8	C29—C30—H30	121.1
C4—C5—H5	119.8	C30—C31—C32	118.6 (5)
C5—C6—C1	120.7 (4)	C30—C31—H31	120.7
C5—C6—H6	119.7	C32—C31—H31	120.7
C1—C6—H6	119.7	C33—C32—C31	120.5 (5)
N1—C7—C1	125.0 (4)	C33—C32—H32	119.8
N1—C7—H7A	117.5	C31—C32—H32	119.8
C1—C7—H7A	117.5	N3—C33—C32	121.5 (5)
C13—C8—C9	119.0 (3)	N3—C33—H33	119.2
C13—C8—C14	122.4 (3)	C32—C33—H33	119.2
C9—C8—C14	118.5 (3)	N4—C34—C35	124.3 (6)
C10—C9—C8	121.7 (4)	N4—C34—H34	117.9
C10—C9—H9	119.2	C35—C34—H34	117.9
C8—C9—H9	119.2	C36—C35—C34	118.6 (6)
C9—C10—C11	118.7 (4)	C36—C35—H35	120.7
C9—C10—H10	120.6	C34—C35—H35	120.7
C11—C10—H10	120.6	C35—C36—C37	119.6 (6)
C12—C11—C10	122.1 (4)	C35—C36—H36	120.2
C12—C11—H11	118.9	C37—C36—H36	120.2
C10—C11—H11	118.9	C38—C37—C36	117.4 (6)
C11—C12—C13	121.0 (4)	C38—C37—H37	121.3
C11—C12—H12	119.5	C36—C37—H37	121.3
C13—C12—H12	119.5	N4—C38—C37	123.2 (5)
O2—C13—C8	123.2 (3)	N4—C38—H38	118.4
O2—C13—C12	119.4 (4)	C37—C38—H38	118.4
C8—C13—C12	117.4 (4)	O7—C39—H39A	109.5
N2—C14—C8	124.4 (3)	O7—C39—H39B	109.5
N2—C14—H14	117.8	H39A—C39—H39B	109.5
C8—C14—H14	117.8	O7—C39—H39C	109.5
N1—C15—C17	114.8 (3)	H39A—C39—H39C	109.5
N1—C15—C16	108.0 (3)	H39B—C39—H39C	109.5
C17—C15—C16	111.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8D···O6^i	0.85	1.98	2.831 (14)	178
O8—H8C···O7	0.85	1.96	2.807 (19)	177
O7—H7···O2	0.82	2.08	2.897 (11)	171

Symmetry code: (i) x+1, y, z.