[(-)-(1S,2S)-N,N'-Bis(2-oxidobenzyl-idene)-1,2-diphenyl-ethane-1,2-diamine]-bis-(pyridine)cobalt(III) perchlorate methanol hemisolvate hemihydrate.

In the title compound, [Co(C(28)H(22)N(2)O(2))(C(5)H(5)N)(2)]ClO(4)·0.5CH(4)O·0.5H(2)O, each Co(III) ion is coordinated by the tetra-dentate N,N'-bis-(2-oxidobenzyl-idene)-1,2-diphenyl-ethane-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 octa-hedral geometry. The packing of the cations and anions forms voids of 258 Å(3), which are filled by methanol and solvent water mol-ecules 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.

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 ▶).

Experimental

Crystal data

[Co(C28H22N2O2)(C5H5N)2]ClO4·0.5CH4O·0.5H2O

M = 760.09

Orthorhombic,

a = 10.8900 (3) Å

b = 18.6219 (5) Å

c = 18.6557 (6) Å

V = 3783.24 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.58 mm−1

T = 273 (2) K

0.18 × 0.16 × 0.14 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.903, T max = 0.924

42911 measured reflections

7407 independent reflections

5476 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.145

S = 1.02

7407 reflections

463 parameters

13 restraints

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.37 e Å−3

Absolute structure: Flack (1983 ▶), with 3248 Friedel pairs

Flack parameter: 0.03 (2)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808031887/cv2457sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031887/cv2457Isup2.hkl

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

[Co(C28H22N2O2)(C5H5N)2]ClO4·0.5CH4O·0.5H2O	Dx = 1.334 Mg m−3Dm = 1.334 Mg m−3Dm 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) Å3	Block, red-brown
Z = 4	0.18 × 0.16 × 0.14 mm
F(000) = 1576

Bruker APEXII CCD area-detector diffractometer	7407 independent reflections
Radiation source: fine-focus sealed tube	5476 reflections with I > 2σ(I)
graphite	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 on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.050	w = 1/[σ2(Fo2) + (0.0885P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 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+0.001xFc2λ3/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	Flack parameter: 0.03 (2)

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	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

	U11	U22	U33	U12	U13	U23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8D···O6i	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

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8D⋯O6i	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) .