{(+)-(1R,2R)-1,2-Diphenyl-2,2'-[ethane-1,2-diylbis(nitrilo-methyl-idyne)]-di-phenol-ato}dipyridine-cobalt(III) perchlorate sesquihydrate.

In title complex, [Co(C(28)H(22)N(2)O(2))(C(5)H(5)N)(2)]ClO(4)·1.5H(2)O, the Co(III) ion is in a slightly distorted octa-hedral coordination environment with the pyridine ligands in a trans arrangement. In addition to the cation and anion, the asymmetric unit also contains three half-occupancy solvent water mol-ecules and all components are connected via inter-molecular O-H⋯O hydrogen bonds.

Related literature

For background information, see: Amirnasr et al. (2001 ▶); Cmi et al. (1998 ▶); Polson et al. (1997 ▶); Yamada (1999 ▶); Henson et al. (1999 ▶). For the synthethis of the parent Schiff base ligand, see: Zhang et al. (1990 ▶). For a related structure, see: Shi et al. (1995 ▶).

Experimental

Crystal data

[Co(C28H22N2O2)(C5H5N)2]ClO4·1.5H2O

M = 762.08

Orthorhombic,

a = 10.9214 (6) Å

b = 18.3856 (10) Å

c = 18.6714 (11) Å

V = 3749.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.58 mm−1

T = 293 (2) K

0.21 × 0.16 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.887, T max = 0.928

20101 measured reflections

7290 independent reflections

4733 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.127

S = 0.99

7290 reflections

480 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.29 e Å−3

Absolute structure: Flack (1983 ▶), with 3227 Friedel pairs

Flack parameter: 0.02 (2)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809002293/lh2754sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002293/lh2754Isup2.hkl

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

[Co(C28H22N2O2)(C5H5N)2]ClO4·1.5H2O	F(000) = 1580
Mr = 762.08	Dx = 1.350 Mg m−3Dm = 1.35 Mg m−3Dm measured by not measured
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2979 reflections
a = 10.9214 (6) Å	θ = 2.4–20.0°
b = 18.3856 (10) Å	µ = 0.58 mm−1
c = 18.6714 (11) Å	T = 293 K
V = 3749.2 (4) Å3	Block, red-brown
Z = 4	0.21 × 0.16 × 0.13 mm

Bruker APEXII CCD area-detector diffractometer	7290 independent reflections
Radiation source: fine-focus sealed tube	4733 reflections with I > 2σ(I)
graphite	Rint = 0.059
φ and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→13
Tmin = 0.887, Tmax = 0.928	k = −20→22
20101 measured reflections	l = −22→23

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H-atom parameters constrained
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0572P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
7290 reflections	Δρmax = 0.51 e Å−3
480 parameters	Δρmin = −0.29 e Å−3
0 restraints	Absolute structure: Flack (1983), with 3227 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (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	0.24611 (5)	0.00305 (3)	0.17215 (3)	0.03757 (15)
Cl1	0.35527 (13)	0.30536 (8)	0.25408 (9)	0.0736 (4)
O1	0.1518 (3)	−0.08004 (15)	0.19449 (15)	0.0469 (8)
O2	0.1443 (3)	0.01550 (15)	0.09181 (14)	0.0437 (7)
O3	0.3774 (4)	0.24263 (19)	0.2999 (3)	0.0960 (14)
O4	0.2856 (5)	0.3577 (2)	0.2928 (3)	0.1116 (16)
O5	0.4678 (4)	0.3364 (2)	0.2330 (3)	0.0932 (14)
O6	0.2887 (4)	0.2832 (3)	0.1939 (3)	0.1289 (19)
O7	0.5661 (8)	0.6832 (4)	0.9108 (4)	0.088 (3)	0.50
H7C	0.4884	0.6827	0.9136	0.106*	0.50
H7D	0.5880	0.6522	0.8796	0.106*	0.50
O8	0.3200 (8)	0.6862 (5)	0.9246 (4)	0.103 (3)	0.50
H8C	0.2789	0.7231	0.9380	0.124*	0.50
H8D	0.2910	0.6716	0.8849	0.124*	0.50
O9	0.1910 (8)	0.7977 (6)	0.9603 (5)	0.123 (4)	0.50
H9C	0.1551	0.7868	0.9214	0.148*	0.50
H9D	0.1378	0.8014	0.9933	0.148*	0.50
N1	0.3507 (3)	−0.00967 (18)	0.25272 (17)	0.0388 (8)
N2	0.3455 (3)	0.08553 (18)	0.15341 (17)	0.0367 (8)
N3	0.3501 (4)	−0.0582 (2)	0.1098 (2)	0.0449 (9)
N4	0.1290 (3)	0.06249 (19)	0.22734 (19)	0.0407 (9)
C1	0.2065 (4)	−0.0821 (2)	0.3196 (2)	0.0408 (10)
C2	0.1272 (4)	−0.0988 (2)	0.2617 (2)	0.0428 (11)
C3	0.0206 (5)	−0.1379 (3)	0.2778 (3)	0.0560 (13)
H3	−0.0320	−0.1509	0.2408	0.067*
C4	−0.0077 (5)	−0.1571 (3)	0.3452 (3)	0.0629 (15)
H4	−0.0801	−0.1823	0.3537	0.076*
C5	0.0679 (5)	−0.1406 (3)	0.4024 (3)	0.0601 (14)
H5	0.0466	−0.1538	0.4489	0.072*
C6	0.1756 (4)	−0.1041 (2)	0.3888 (3)	0.0490 (12)
H6	0.2287	−0.0938	0.4264	0.059*
C7	0.3216 (4)	−0.0458 (2)	0.3094 (2)	0.0412 (11)
H7	0.3789	−0.0486	0.3461	0.049*
C8	0.2062 (4)	0.1393 (2)	0.0670 (2)	0.0421 (11)
C9	0.1321 (4)	0.0775 (3)	0.0570 (2)	0.0403 (10)
C10	0.0392 (4)	0.0813 (3)	0.0046 (2)	0.0480 (12)
H10	−0.0084	0.0406	−0.0050	0.058*
C11	0.0183 (4)	0.1454 (3)	−0.0326 (2)	0.0538 (13)
H11	−0.0443	0.1472	−0.0663	0.065*
C12	0.0887 (5)	0.2064 (3)	−0.0203 (3)	0.0511 (13)
H12	0.0726	0.2492	−0.0451	0.061*
C13	0.1821 (4)	0.2038 (3)	0.0282 (2)	0.0472 (12)
H13	0.2303	0.2448	0.0358	0.057*
C14	0.3136 (4)	0.1386 (3)	0.1134 (2)	0.0408 (11)
H14	0.3626	0.1799	0.1139	0.049*
C15	0.4731 (4)	0.0235 (2)	0.2419 (2)	0.0394 (10)
H15	0.5198	−0.0089	0.2104	0.047*
C16	0.4541 (4)	0.0942 (2)	0.2025 (2)	0.0377 (10)
H16	0.4319	0.1309	0.2384	0.045*
C17	0.5483 (4)	0.0344 (2)	0.3105 (2)	0.0432 (11)
C18	0.6548 (4)	−0.0041 (3)	0.3210 (3)	0.0573 (11)
H18	0.6797	−0.0381	0.2871	0.069*
C19	0.7252 (5)	0.0073 (4)	0.3816 (3)	0.0746 (15)
H19	0.7963	−0.0196	0.3886	0.089*
C20	0.6908 (6)	0.0581 (4)	0.4313 (4)	0.0787 (19)
H20	0.7392	0.0662	0.4715	0.094*
C21	0.5833 (6)	0.0977 (3)	0.4217 (3)	0.0755 (17)
H21	0.5593	0.1321	0.4553	0.091*
C22	0.5124 (5)	0.0850 (3)	0.3614 (3)	0.0587 (14)
H22	0.4400	0.1107	0.3550	0.070*
C23	0.5701 (4)	0.1209 (2)	0.1656 (2)	0.0417 (10)
C24	0.6226 (5)	0.0834 (3)	0.1097 (3)	0.0610 (14)
H24	0.5848	0.0419	0.0918	0.073*
C25	0.7327 (5)	0.1077 (3)	0.0797 (3)	0.0687 (15)
H25	0.7678	0.0826	0.0417	0.082*
C26	0.7883 (5)	0.1682 (3)	0.1062 (3)	0.0606 (15)
H26	0.8616	0.1840	0.0862	0.073*
C27	0.7379 (5)	0.2061 (2)	0.1619 (3)	0.0544 (12)
H27	0.7770	0.2472	0.1798	0.065*
C28	0.6272 (4)	0.1827 (2)	0.1917 (2)	0.0439 (11)
H28	0.5919	0.2087	0.2290	0.053*
C29	0.3837 (5)	−0.1252 (3)	0.1278 (3)	0.0616 (15)
H29	0.3636	−0.1419	0.1733	0.074*
C30	0.4459 (7)	−0.1706 (3)	0.0833 (4)	0.088 (2)
H30	0.4667	−0.2174	0.0978	0.105*
C31	0.4777 (6)	−0.1458 (4)	0.0160 (4)	0.087 (2)
H31	0.5205	−0.1756	−0.0155	0.104*
C32	0.4457 (6)	−0.0779 (4)	−0.0031 (3)	0.0739 (17)
H32	0.4680	−0.0599	−0.0478	0.089*
C33	0.3795 (5)	−0.0349 (3)	0.0439 (3)	0.0547 (13)
H33	0.3548	0.0112	0.0294	0.066*
C34	0.1608 (4)	0.1158 (2)	0.2719 (2)	0.0487 (12)
H34	0.2436	0.1256	0.2785	0.058*
C35	0.0761 (5)	0.1572 (3)	0.3087 (3)	0.0648 (15)
H35	0.1015	0.1944	0.3391	0.078*
C36	−0.0459 (5)	0.1425 (3)	0.2998 (3)	0.0732 (16)
H36	−0.1049	0.1686	0.3249	0.088*
C37	−0.0793 (5)	0.0884 (3)	0.2533 (3)	0.0661 (15)
H37	−0.1618	0.0782	0.2460	0.079*
C38	0.0086 (4)	0.0492 (3)	0.2173 (3)	0.0496 (12)
H38	−0.0154	0.0129	0.1855	0.060*

	U11	U22	U33	U12	U13	U23
Co1	0.0380 (3)	0.0441 (3)	0.0307 (2)	−0.0055 (3)	−0.0038 (3)	0.0024 (3)
Cl1	0.0614 (9)	0.0627 (8)	0.0966 (11)	0.0083 (7)	−0.0118 (9)	−0.0187 (8)
O1	0.0477 (18)	0.0533 (18)	0.0398 (19)	−0.0136 (16)	−0.0067 (15)	0.0072 (14)
O2	0.0463 (17)	0.0517 (19)	0.0331 (16)	−0.0078 (15)	−0.0100 (13)	0.0051 (14)
O3	0.101 (3)	0.055 (2)	0.132 (4)	0.005 (2)	−0.002 (3)	−0.001 (2)
O4	0.127 (4)	0.087 (3)	0.121 (4)	0.035 (3)	0.032 (3)	−0.011 (3)
O5	0.057 (2)	0.098 (3)	0.124 (4)	−0.008 (2)	−0.002 (3)	0.012 (3)
O6	0.103 (4)	0.153 (4)	0.131 (4)	0.010 (3)	−0.049 (3)	−0.046 (4)
O7	0.098 (6)	0.118 (7)	0.047 (5)	0.066 (5)	−0.001 (4)	−0.044 (5)
O8	0.116 (7)	0.148 (8)	0.046 (5)	0.011 (6)	−0.024 (5)	0.004 (5)
O9	0.088 (7)	0.195 (11)	0.087 (7)	−0.027 (7)	−0.009 (5)	−0.009 (7)
N1	0.0372 (18)	0.0435 (19)	0.0358 (19)	−0.0038 (18)	−0.0029 (15)	−0.0018 (18)
N2	0.0333 (19)	0.044 (2)	0.032 (2)	−0.0011 (17)	−0.0010 (16)	−0.0020 (16)
N3	0.049 (2)	0.049 (2)	0.036 (2)	0.000 (2)	−0.0080 (19)	−0.0043 (17)
N4	0.039 (2)	0.049 (2)	0.034 (2)	−0.0047 (18)	0.0004 (17)	0.0069 (17)
C1	0.039 (2)	0.045 (2)	0.038 (3)	0.001 (2)	−0.005 (2)	0.004 (2)
C2	0.043 (3)	0.044 (2)	0.041 (3)	−0.003 (2)	−0.005 (2)	0.008 (2)
C3	0.048 (3)	0.061 (3)	0.058 (3)	−0.014 (3)	−0.009 (3)	0.017 (3)
C4	0.046 (3)	0.079 (4)	0.064 (4)	−0.019 (3)	−0.002 (3)	0.025 (3)
C5	0.047 (3)	0.076 (4)	0.058 (4)	−0.001 (3)	0.006 (3)	0.013 (3)
C6	0.046 (3)	0.056 (3)	0.044 (3)	0.000 (2)	−0.003 (2)	0.009 (2)
C7	0.042 (3)	0.048 (3)	0.034 (3)	0.001 (2)	−0.007 (2)	0.004 (2)
C8	0.043 (3)	0.051 (3)	0.032 (3)	0.000 (2)	0.0064 (19)	0.002 (2)
C9	0.040 (3)	0.054 (3)	0.027 (2)	0.001 (2)	0.0042 (19)	−0.002 (2)
C10	0.040 (3)	0.070 (3)	0.034 (3)	0.003 (3)	0.000 (2)	0.002 (2)
C11	0.042 (3)	0.083 (4)	0.037 (3)	0.013 (3)	−0.001 (2)	0.011 (3)
C12	0.050 (3)	0.062 (3)	0.042 (3)	0.011 (3)	0.005 (2)	0.017 (2)
C13	0.051 (3)	0.054 (3)	0.037 (3)	0.004 (2)	0.005 (2)	0.009 (2)
C14	0.041 (3)	0.046 (3)	0.036 (3)	−0.007 (2)	0.002 (2)	0.000 (2)
C15	0.032 (2)	0.047 (3)	0.039 (3)	−0.0034 (19)	−0.0050 (19)	−0.001 (2)
C16	0.035 (2)	0.043 (2)	0.035 (2)	−0.005 (2)	−0.0020 (19)	−0.002 (2)
C17	0.038 (2)	0.049 (3)	0.043 (3)	−0.006 (2)	−0.008 (2)	0.007 (2)
C18	0.044 (3)	0.066 (3)	0.062 (3)	−0.006 (3)	−0.007 (2)	0.006 (3)
C19	0.054 (3)	0.094 (4)	0.076 (4)	−0.005 (4)	−0.020 (3)	0.013 (4)
C20	0.069 (4)	0.096 (5)	0.071 (4)	−0.025 (4)	−0.028 (3)	0.023 (4)
C21	0.087 (4)	0.078 (4)	0.061 (4)	−0.008 (3)	−0.021 (4)	−0.003 (3)
C22	0.063 (3)	0.068 (3)	0.045 (3)	0.004 (3)	−0.016 (3)	−0.002 (3)
C23	0.035 (2)	0.050 (3)	0.040 (3)	0.001 (2)	0.001 (2)	0.002 (2)
C24	0.056 (3)	0.070 (3)	0.057 (3)	−0.011 (3)	0.012 (3)	−0.013 (3)
C25	0.052 (3)	0.087 (4)	0.067 (3)	−0.006 (3)	0.022 (3)	−0.012 (3)
C26	0.040 (3)	0.075 (4)	0.066 (4)	−0.006 (3)	0.011 (2)	0.014 (3)
C27	0.048 (3)	0.052 (3)	0.064 (3)	−0.005 (3)	0.005 (3)	0.011 (2)
C28	0.040 (3)	0.044 (2)	0.047 (3)	−0.001 (2)	0.001 (2)	0.004 (2)
C29	0.073 (4)	0.060 (3)	0.051 (3)	0.010 (3)	−0.010 (3)	−0.006 (3)
C30	0.111 (5)	0.077 (4)	0.075 (5)	0.037 (4)	−0.014 (4)	−0.014 (4)
C31	0.093 (5)	0.093 (5)	0.075 (5)	0.033 (4)	−0.002 (4)	−0.028 (4)
C32	0.088 (5)	0.082 (4)	0.051 (3)	0.010 (4)	0.005 (3)	−0.010 (3)
C33	0.061 (3)	0.058 (3)	0.045 (3)	−0.003 (3)	0.002 (3)	−0.012 (2)
C34	0.040 (3)	0.060 (3)	0.047 (3)	−0.002 (2)	0.006 (2)	−0.002 (2)
C35	0.066 (4)	0.069 (3)	0.059 (4)	0.010 (3)	0.009 (3)	−0.013 (3)
C36	0.055 (4)	0.088 (4)	0.076 (4)	0.016 (3)	0.016 (3)	0.003 (4)
C37	0.041 (3)	0.093 (4)	0.064 (4)	0.007 (3)	0.008 (3)	0.013 (3)
C38	0.041 (3)	0.061 (3)	0.047 (3)	−0.003 (2)	−0.002 (2)	0.009 (2)

Co1—O2	1.881 (3)	C13—H13	0.9300
Co1—O1	1.889 (3)	C14—H14	0.9300
Co1—N2	1.897 (3)	C15—C16	1.509 (6)
Co1—N1	1.904 (3)	C15—C17	1.534 (6)
Co1—N4	1.973 (4)	C15—H15	0.9800
Co1—N3	1.978 (4)	C16—C23	1.524 (6)
Cl1—O6	1.400 (5)	C16—H16	0.9800
Cl1—O5	1.412 (4)	C17—C18	1.376 (6)
Cl1—O4	1.424 (4)	C17—C22	1.387 (6)
Cl1—O3	1.456 (4)	C18—C19	1.383 (7)
O1—C2	1.329 (5)	C18—H18	0.9300
O2—C9	1.318 (5)	C19—C20	1.369 (8)
O7—H7C	0.8501	C19—H19	0.9300
O7—H7D	0.8499	C20—C21	1.393 (8)
O8—H8C	0.8500	C20—H20	0.9300
O8—H8D	0.8500	C21—C22	1.386 (7)
O9—H9C	0.8500	C21—H21	0.9300
O9—H9D	0.8500	C22—H22	0.9300
N1—C7	1.290 (5)	C23—C24	1.374 (6)
N1—C15	1.482 (5)	C23—C28	1.385 (6)
N2—C14	1.277 (5)	C24—C25	1.400 (7)
N2—C16	1.508 (5)	C24—H24	0.9300
N3—C29	1.328 (6)	C25—C26	1.359 (7)
N3—C33	1.342 (6)	C25—H25	0.9300
N4—C34	1.332 (5)	C26—C27	1.366 (7)
N4—C38	1.351 (5)	C26—H26	0.9300
C1—C6	1.395 (6)	C27—C28	1.398 (6)
C1—C2	1.418 (6)	C27—H27	0.9300
C1—C7	1.436 (6)	C28—H28	0.9300
C2—C3	1.401 (6)	C29—C30	1.361 (8)
C3—C4	1.343 (7)	C29—H29	0.9300
C3—H3	0.9300	C30—C31	1.380 (9)
C4—C5	1.383 (7)	C30—H30	0.9300
C4—H4	0.9300	C31—C32	1.345 (9)
C5—C6	1.378 (7)	C31—H31	0.9300
C5—H5	0.9300	C32—C33	1.385 (7)
C6—H6	0.9300	C32—H32	0.9300
C7—H7	0.9300	C33—H33	0.9300
C8—C9	1.408 (6)	C34—C35	1.381 (6)
C8—C13	1.414 (6)	C34—H34	0.9300
C8—C14	1.459 (6)	C35—C36	1.370 (8)
C9—C10	1.412 (6)	C35—H35	0.9300
C10—C11	1.386 (7)	C36—C37	1.369 (8)
C10—H10	0.9300	C36—H36	0.9300
C11—C12	1.379 (7)	C37—C38	1.376 (7)
C11—H11	0.9300	C37—H37	0.9300
C12—C13	1.365 (7)	C38—H38	0.9300
C12—H12	0.9300
O2—Co1—O1	87.26 (12)	C8—C14—H14	117.5
O2—Co1—N2	95.39 (13)	N1—C15—C16	107.3 (3)
O1—Co1—N2	177.35 (14)	N1—C15—C17	115.0 (3)
O2—Co1—N1	179.34 (15)	C16—C15—C17	111.6 (3)
O1—Co1—N1	93.06 (13)	N1—C15—H15	107.6
N2—Co1—N1	84.29 (15)	C16—C15—H15	107.6
O2—Co1—N4	88.04 (14)	C17—C15—H15	107.6
O1—Co1—N4	88.81 (14)	N2—C16—C15	108.3 (3)
N2—Co1—N4	91.41 (14)	N2—C16—C23	114.4 (3)
N1—Co1—N4	92.55 (14)	C15—C16—C23	112.6 (4)
O2—Co1—N3	86.52 (14)	N2—C16—H16	107.1
O1—Co1—N3	88.97 (15)	C15—C16—H16	107.1
N2—Co1—N3	91.06 (15)	C23—C16—H16	107.1
N1—Co1—N3	92.90 (15)	C18—C17—C22	119.0 (4)
N4—Co1—N3	174.22 (16)	C18—C17—C15	120.3 (4)
O6—Cl1—O5	110.2 (3)	C22—C17—C15	120.6 (4)
O6—Cl1—O4	109.1 (3)	C17—C18—C19	120.6 (5)
O5—Cl1—O4	109.5 (3)	C17—C18—H18	119.7
O6—Cl1—O3	109.1 (3)	C19—C18—H18	119.7
O5—Cl1—O3	109.8 (3)	C20—C19—C18	120.3 (6)
O4—Cl1—O3	109.0 (3)	C20—C19—H19	119.8
C2—O1—Co1	121.9 (3)	C18—C19—H19	119.8
C9—O2—Co1	123.9 (3)	C19—C20—C21	120.0 (6)
H7C—O7—H7D	108.5	C19—C20—H20	120.0
H8C—O8—H8D	108.3	C21—C20—H20	120.0
H9C—O9—H9D	108.8	C22—C21—C20	119.2 (6)
C7—N1—C15	123.1 (3)	C22—C21—H21	120.4
C7—N1—Co1	124.3 (3)	C20—C21—H21	120.4
C15—N1—Co1	112.5 (3)	C21—C22—C17	120.8 (5)
C14—N2—C16	119.3 (4)	C21—C22—H22	119.6
C14—N2—Co1	124.2 (3)	C17—C22—H22	119.6
C16—N2—Co1	115.0 (2)	C24—C23—C28	119.3 (4)
C29—N3—C33	117.5 (4)	C24—C23—C16	122.0 (4)
C29—N3—Co1	122.5 (3)	C28—C23—C16	118.6 (4)
C33—N3—Co1	119.7 (3)	C23—C24—C25	120.1 (5)
C34—N4—C38	118.3 (4)	C23—C24—H24	119.9
C34—N4—Co1	124.4 (3)	C25—C24—H24	119.9
C38—N4—Co1	117.3 (3)	C26—C25—C24	119.9 (5)
C6—C1—C2	119.7 (4)	C26—C25—H25	120.0
C6—C1—C7	117.9 (4)	C24—C25—H25	120.0
C2—C1—C7	122.3 (4)	C25—C26—C27	120.9 (5)
O1—C2—C3	120.3 (4)	C25—C26—H26	119.5
O1—C2—C1	122.7 (4)	C27—C26—H26	119.5
C3—C2—C1	117.0 (4)	C26—C27—C28	119.6 (5)
C4—C3—C2	121.9 (5)	C26—C27—H27	120.2
C4—C3—H3	119.1	C28—C27—H27	120.2
C2—C3—H3	119.1	C23—C28—C27	120.1 (4)
C3—C4—C5	121.9 (5)	C23—C28—H28	119.9
C3—C4—H4	119.1	C27—C28—H28	119.9
C5—C4—H4	119.1	N3—C29—C30	123.5 (6)
C6—C5—C4	118.3 (5)	N3—C29—H29	118.2
C6—C5—H5	120.9	C30—C29—H29	118.2
C4—C5—H5	120.9	C29—C30—C31	118.6 (6)
C5—C6—C1	121.2 (4)	C29—C30—H30	120.7
C5—C6—H6	119.4	C31—C30—H30	120.7
C1—C6—H6	119.4	C32—C31—C30	119.0 (6)
N1—C7—C1	124.4 (4)	C32—C31—H31	120.5
N1—C7—H7	117.8	C30—C31—H31	120.5
C1—C7—H7	117.8	C31—C32—C33	119.8 (6)
C9—C8—C13	120.2 (4)	C31—C32—H32	120.1
C9—C8—C14	122.2 (4)	C33—C32—H32	120.1
C13—C8—C14	117.5 (4)	N3—C33—C32	121.6 (5)
O2—C9—C8	125.1 (4)	N3—C33—H33	119.2
O2—C9—C10	117.2 (4)	C32—C33—H33	119.2
C8—C9—C10	117.7 (4)	N4—C34—C35	122.8 (5)
C11—C10—C9	120.6 (5)	N4—C34—H34	118.6
C11—C10—H10	119.7	C35—C34—H34	118.6
C9—C10—H10	119.7	C36—C35—C34	118.8 (5)
C12—C11—C10	121.0 (5)	C36—C35—H35	120.6
C12—C11—H11	119.5	C34—C35—H35	120.6
C10—C11—H11	119.5	C37—C36—C35	118.7 (5)
C13—C12—C11	119.9 (5)	C37—C36—H36	120.7
C13—C12—H12	120.0	C35—C36—H36	120.7
C11—C12—H12	120.0	C36—C37—C38	120.3 (5)
C12—C13—C8	120.5 (5)	C36—C37—H37	119.9
C12—C13—H13	119.8	C38—C37—H37	119.9
C8—C13—H13	119.8	N4—C38—C37	121.1 (5)
N2—C14—C8	125.0 (4)	N4—C38—H38	119.4
N2—C14—H14	117.5	C37—C38—H38	119.4

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7C···O8	0.85	1.85	2.701 (12)	176
O7—H7D···O1i	0.85	2.04	2.888 (8)	176
O8—H8C···O9	0.85	1.73	2.575 (14)	177
O8—H8D···O4ii	0.85	1.99	2.835 (10)	176
O9—H9C···O3ii	0.85	2.36	3.175 (11)	161

Table 1

Selected bond lengths (Å)

Co1—O2	1.881 (3)
Co1—O1	1.889 (3)
Co1—N2	1.897 (3)
Co1—N1	1.904 (3)
Co1—N4	1.973 (4)
Co1—N3	1.978 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7C⋯O8	0.85	1.85	2.701 (12)	176
O7—H7D⋯O1i	0.85	2.04	2.888 (8)	176
O8—H8C⋯O9	0.85	1.73	2.575 (14)	177
O8—H8D⋯O4ii	0.85	1.99	2.835 (10)	176
O9—H9C⋯O3ii	0.85	2.36	3.175 (11)	161

Symmetry codes: (i) ; (ii) .