Chloridobis[N'-(2-meth-oxy-benzyl-idene)-4-nitro-benzohydrazidato-κO,N'](4-methyl-pyridine-κN)cobalt(III).

In the title complex, [Co(C(15)H(12)N(3)O(4))(2)Cl(C(6)H(7)N)], the Co(III) ion is coordinated by two N atoms and two O atoms from two deprotonated Schiff base ligands, one N atom from a 4-methyl-pyridine ligand and one Cl atom, forming a distorted octa-hedral geometry. The Co(III) ion is displaced by 0.038 (2) Å from the equatorial plane towards the axial Cl atom.

Related literature

For general background to aroylhydrazines and their metal complexes, see: Cariati et al. (2002 ▶); Chen et al. (2010 ▶); Fun et al. (1996 ▶); Liao et al. (2000 ▶); Liu & Gao (1998 ▶); Lu et al. (1996 ▶); Tai et al. (2003 ▶); Xue & Liu (2006 ▶); Yang & Pan (2004 ▶). For related structures, see: Chen & Liu (2006 ▶); Tan et al. (2010 ▶); Wu & Liu (2004 ▶).

Experimental

Crystal data

[Co(C15H12N3O4)2Cl(C6H7N)]

M = 784.06

Triclinic,

a = 10.530 (2) Å

b = 14.028 (3) Å

c = 14.794 (3) Å

α = 62.203 (3)°

β = 85.669 (3)°

γ = 72.275 (3)°

V = 1835.6 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.60 mm−1

T = 293 K

0.12 × 0.10 × 0.08 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.931, T max = 0.954

12688 measured reflections

6308 independent reflections

3144 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.157

S = 0.94

6308 reflections

478 parameters

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.29 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811003321/hy2400sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003321/hy2400Isup2.hkl

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

[Co(C15H12N3O4)2Cl(C6H7N)]	Z = 2
Mr = 784.06	F(000) = 808
Triclinic, P1	Dx = 1.419 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.530 (2) Å	Cell parameters from 3144 reflections
b = 14.028 (3) Å	θ = 2.0–25.0°
c = 14.794 (3) Å	µ = 0.60 mm−1
α = 62.203 (3)°	T = 293 K
β = 85.669 (3)°	Prism, brown
γ = 72.275 (3)°	0.12 × 0.10 × 0.08 mm
V = 1835.6 (7) Å3

Rigaku R-AXIS RAPID diffractometer	6308 independent reflections
Radiation source: rotation anode	3144 reflections with I > 2σ(I)
graphite	Rint = 0.064
ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→12
Tmin = 0.931, Tmax = 0.954	k = −16→14
12688 measured reflections	l = −17→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H-atom parameters constrained
S = 0.94	w = 1/[σ2(Fo2) + (0.0697P)2] where P = (Fo2 + 2Fc2)/3
6308 reflections	(Δ/σ)max = 0.001
478 parameters	Δρmax = 0.73 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

	x	y	z	Uiso*/Ueq
Co1	0.37392 (7)	0.10485 (6)	0.26462 (5)	0.0404 (2)
Cl1	0.56482 (14)	−0.04002 (12)	0.31714 (10)	0.0594 (4)
O1	0.7244 (6)	0.5110 (5)	0.4349 (4)	0.128 (2)
O2	0.6499 (5)	0.4123 (4)	0.5748 (4)	0.1036 (16)
O3	0.4228 (3)	0.1646 (3)	0.3428 (2)	0.0454 (9)
O4	0.4954 (4)	0.2019 (3)	−0.1040 (3)	0.0698 (11)
O5	−0.0960 (7)	0.1461 (6)	−0.2398 (5)	0.145 (3)
O6	0.0849 (7)	0.0090 (6)	−0.2185 (5)	0.134 (2)
O7	0.3203 (3)	0.0612 (3)	0.1748 (2)	0.0427 (8)
O8	0.1019 (4)	0.4428 (4)	0.3188 (4)	0.0871 (14)
N1	0.6684 (6)	0.4408 (5)	0.4845 (4)	0.0769 (16)
N2	0.5113 (4)	0.2641 (4)	0.1940 (3)	0.0493 (11)
N3	0.4654 (4)	0.2001 (3)	0.1626 (3)	0.0439 (10)
N4	0.0158 (9)	0.0820 (8)	−0.1975 (5)	0.103 (2)
N5	0.1387 (4)	0.2219 (4)	0.1352 (3)	0.0468 (11)
N6	0.2066 (4)	0.2250 (4)	0.2103 (3)	0.0435 (11)
N7	0.2841 (4)	0.0135 (3)	0.3809 (3)	0.0409 (10)
C1	0.5279 (5)	0.2942 (4)	0.3384 (4)	0.0439 (13)
C2	0.4979 (5)	0.2702 (4)	0.4383 (4)	0.0496 (14)
H2B	0.4478	0.2211	0.4725	0.060*
C3	0.5420 (5)	0.3184 (5)	0.4871 (4)	0.0558 (15)
H3A	0.5225	0.3027	0.5540	0.067*
C4	0.6163 (6)	0.3909 (5)	0.4334 (4)	0.0527 (14)
C5	0.6444 (6)	0.4179 (5)	0.3343 (4)	0.0570 (15)
H5B	0.6917	0.4693	0.2996	0.068*
C6	0.6020 (5)	0.3684 (5)	0.2872 (4)	0.0543 (15)
H6A	0.6227	0.3843	0.2204	0.065*
C7	0.4835 (5)	0.2372 (4)	0.2892 (4)	0.0425 (12)
C8	0.4890 (5)	0.2082 (4)	0.0719 (3)	0.0481 (14)
H8A	0.4581	0.1616	0.0565	0.058*
C9	0.5563 (5)	0.2793 (5)	−0.0091 (4)	0.0532 (14)
C10	0.5598 (6)	0.2723 (5)	−0.1022 (4)	0.0565 (15)
C11	0.6177 (6)	0.3369 (6)	−0.1841 (4)	0.0749 (19)
H11A	0.6169	0.3330	−0.2450	0.090*
C12	0.6774 (7)	0.4083 (7)	−0.1765 (5)	0.090 (2)
H12A	0.7174	0.4516	−0.2324	0.108*
C13	0.6782 (7)	0.4160 (6)	−0.0861 (5)	0.091 (2)
H13A	0.7186	0.4641	−0.0813	0.109*
C14	0.6187 (7)	0.3515 (6)	−0.0040 (4)	0.0764 (19)
H14A	0.6200	0.3562	0.0566	0.092*
C15	0.4867 (8)	0.1978 (6)	−0.1990 (5)	0.100 (2)
H15A	0.4389	0.1461	−0.1904	0.151*
H15B	0.5752	0.1726	−0.2179	0.151*
H15C	0.4403	0.2718	−0.2520	0.151*
C16	0.1556 (6)	0.1187 (4)	0.0397 (4)	0.0505 (14)
C17	0.2401 (6)	0.0517 (5)	0.0012 (4)	0.0685 (17)
H17A	0.3286	0.0142	0.0279	0.082*
C18	0.1936 (7)	0.0404 (6)	−0.0764 (5)	0.0777 (19)
H18A	0.2501	−0.0052	−0.1019	0.093*
C19	0.0650 (8)	0.0960 (6)	−0.1154 (5)	0.0727 (19)
C20	−0.0214 (7)	0.1636 (6)	−0.0792 (5)	0.0756 (19)
H20A	−0.1092	0.2016	−0.1075	0.091*
C21	0.0238 (6)	0.1743 (5)	−0.0009 (4)	0.0667 (17)
H21A	−0.0339	0.2189	0.0250	0.080*
C22	0.2089 (6)	0.1335 (5)	0.1225 (4)	0.0441 (13)
C23	0.1556 (6)	0.3046 (5)	0.2358 (4)	0.0490 (14)
H23A	0.2047	0.2987	0.2888	0.059*
C24	0.0358 (5)	0.4014 (5)	0.1967 (4)	0.0472 (13)
C25	0.0126 (7)	0.4728 (5)	0.2425 (5)	0.0591 (16)
C26	−0.0976 (8)	0.5700 (6)	0.2070 (6)	0.077 (2)
H26A	−0.1120	0.6183	0.2359	0.093*
C27	−0.1858 (7)	0.5946 (6)	0.1285 (6)	0.0777 (19)
H27A	−0.2587	0.6600	0.1049	0.093*
C28	−0.1675 (7)	0.5250 (6)	0.0855 (5)	0.0713 (18)
H28A	−0.2287	0.5417	0.0341	0.086*
C29	−0.0568 (6)	0.4283 (5)	0.1188 (4)	0.0626 (16)
H29A	−0.0442	0.3811	0.0888	0.075*
C30	0.0780 (8)	0.5059 (8)	0.3742 (7)	0.133 (3)
H30A	0.1499	0.4739	0.4260	0.199*
H30B	−0.0047	0.5033	0.4059	0.199*
H30C	0.0728	0.5831	0.3280	0.199*
C31	0.2877 (5)	0.0132 (5)	0.4712 (4)	0.0539 (15)
H31A	0.3369	0.0541	0.4792	0.065*
C32	0.2223 (5)	−0.0445 (5)	0.5528 (4)	0.0597 (16)
H32A	0.2257	−0.0399	0.6133	0.072*
C33	0.1520 (5)	−0.1088 (5)	0.5453 (5)	0.0617 (16)
C34	0.1506 (6)	−0.1112 (5)	0.4531 (5)	0.0687 (18)
H34A	0.1052	−0.1541	0.4445	0.082*
C35	0.2171 (6)	−0.0495 (5)	0.3735 (4)	0.0632 (16)
H35A	0.2149	−0.0522	0.3121	0.076*
C36	0.0757 (6)	−0.1717 (5)	0.6334 (5)	0.088 (2)
H36A	0.0882	−0.1598	0.6905	0.131*
H36B	0.1087	−0.2512	0.6534	0.131*
H36C	−0.0178	−0.1439	0.6116	0.131*

	U11	U22	U33	U12	U13	U23
Co1	0.0446 (5)	0.0485 (5)	0.0383 (4)	−0.0235 (4)	0.0059 (3)	−0.0229 (3)
Cl1	0.0574 (9)	0.0657 (10)	0.0590 (9)	−0.0195 (8)	0.0010 (7)	−0.0313 (8)
O1	0.187 (6)	0.188 (6)	0.110 (4)	−0.154 (5)	0.063 (4)	−0.097 (4)
O2	0.162 (5)	0.130 (4)	0.067 (3)	−0.087 (4)	0.019 (3)	−0.060 (3)
O3	0.053 (2)	0.058 (2)	0.0385 (19)	−0.032 (2)	0.0124 (16)	−0.0246 (17)
O4	0.097 (3)	0.080 (3)	0.047 (2)	−0.029 (3)	0.009 (2)	−0.041 (2)
O5	0.149 (6)	0.187 (6)	0.124 (5)	−0.029 (5)	−0.057 (4)	−0.095 (5)
O6	0.157 (6)	0.192 (7)	0.131 (5)	−0.073 (5)	0.017 (4)	−0.127 (5)
O7	0.045 (2)	0.047 (2)	0.043 (2)	−0.0155 (19)	−0.0015 (17)	−0.0251 (17)
O8	0.073 (3)	0.118 (4)	0.117 (4)	−0.027 (3)	0.008 (3)	−0.094 (3)
N1	0.102 (4)	0.101 (4)	0.063 (4)	−0.055 (4)	0.018 (3)	−0.054 (3)
N2	0.065 (3)	0.057 (3)	0.044 (3)	−0.035 (3)	0.014 (2)	−0.030 (2)
N3	0.055 (3)	0.047 (3)	0.039 (2)	−0.022 (2)	0.005 (2)	−0.024 (2)
N4	0.125 (7)	0.135 (7)	0.074 (4)	−0.060 (6)	−0.016 (4)	−0.053 (5)
N5	0.048 (3)	0.050 (3)	0.047 (3)	−0.015 (2)	−0.001 (2)	−0.026 (2)
N6	0.049 (3)	0.048 (3)	0.037 (2)	−0.021 (2)	0.005 (2)	−0.019 (2)
N7	0.040 (3)	0.045 (3)	0.040 (2)	−0.018 (2)	0.0019 (19)	−0.018 (2)
C1	0.048 (3)	0.051 (3)	0.042 (3)	−0.024 (3)	0.007 (2)	−0.025 (3)
C2	0.063 (4)	0.050 (3)	0.045 (3)	−0.031 (3)	0.016 (3)	−0.023 (3)
C3	0.079 (4)	0.072 (4)	0.042 (3)	−0.040 (3)	0.018 (3)	−0.038 (3)
C4	0.072 (4)	0.060 (4)	0.045 (3)	−0.035 (3)	0.007 (3)	−0.031 (3)
C5	0.075 (4)	0.067 (4)	0.048 (3)	−0.043 (3)	0.016 (3)	−0.030 (3)
C6	0.070 (4)	0.068 (4)	0.046 (3)	−0.041 (3)	0.018 (3)	−0.034 (3)
C7	0.050 (3)	0.045 (3)	0.035 (3)	−0.022 (3)	0.009 (2)	−0.018 (2)
C8	0.055 (3)	0.061 (4)	0.036 (3)	−0.024 (3)	0.009 (3)	−0.026 (3)
C9	0.062 (4)	0.061 (4)	0.038 (3)	−0.020 (3)	0.009 (3)	−0.024 (3)
C10	0.057 (4)	0.060 (4)	0.041 (3)	−0.008 (3)	0.003 (3)	−0.020 (3)
C11	0.075 (5)	0.103 (5)	0.041 (4)	−0.026 (4)	0.016 (3)	−0.030 (4)
C12	0.078 (5)	0.113 (6)	0.055 (4)	−0.041 (5)	0.027 (4)	−0.017 (4)
C13	0.111 (6)	0.111 (6)	0.073 (5)	−0.074 (5)	0.036 (4)	−0.041 (4)
C14	0.111 (5)	0.099 (5)	0.053 (4)	−0.076 (5)	0.030 (3)	−0.038 (4)
C15	0.139 (7)	0.122 (6)	0.057 (4)	−0.037 (5)	0.004 (4)	−0.057 (4)
C16	0.065 (4)	0.047 (3)	0.046 (3)	−0.024 (3)	−0.006 (3)	−0.021 (3)
C17	0.064 (4)	0.084 (5)	0.072 (4)	−0.010 (4)	−0.011 (3)	−0.053 (4)
C18	0.082 (5)	0.094 (5)	0.082 (5)	−0.027 (4)	0.004 (4)	−0.062 (4)
C19	0.084 (5)	0.098 (5)	0.056 (4)	−0.044 (5)	−0.004 (4)	−0.040 (4)
C20	0.073 (5)	0.086 (5)	0.083 (5)	−0.028 (4)	−0.017 (4)	−0.046 (4)
C21	0.060 (4)	0.076 (5)	0.073 (4)	−0.021 (4)	−0.011 (3)	−0.040 (4)
C22	0.049 (4)	0.052 (4)	0.038 (3)	−0.028 (3)	0.007 (3)	−0.020 (3)
C23	0.063 (4)	0.052 (4)	0.045 (3)	−0.027 (3)	0.013 (3)	−0.029 (3)
C24	0.047 (4)	0.043 (3)	0.054 (3)	−0.020 (3)	0.011 (3)	−0.023 (3)
C25	0.064 (4)	0.058 (4)	0.074 (4)	−0.033 (4)	0.023 (4)	−0.039 (4)
C26	0.085 (5)	0.062 (5)	0.103 (6)	−0.034 (4)	0.040 (5)	−0.051 (4)
C27	0.075 (5)	0.059 (5)	0.084 (5)	−0.015 (4)	0.021 (4)	−0.027 (4)
C28	0.075 (5)	0.066 (5)	0.061 (4)	−0.011 (4)	0.000 (3)	−0.026 (4)
C29	0.073 (4)	0.051 (4)	0.060 (4)	−0.012 (4)	0.003 (3)	−0.025 (3)
C30	0.099 (6)	0.204 (9)	0.186 (9)	−0.052 (6)	0.032 (6)	−0.163 (8)
C31	0.054 (4)	0.067 (4)	0.046 (3)	−0.032 (3)	0.009 (3)	−0.023 (3)
C32	0.068 (4)	0.063 (4)	0.046 (3)	−0.032 (4)	0.014 (3)	−0.019 (3)
C33	0.048 (4)	0.057 (4)	0.060 (4)	−0.016 (3)	0.007 (3)	−0.012 (3)
C34	0.065 (4)	0.069 (4)	0.072 (4)	−0.042 (4)	0.007 (3)	−0.020 (4)
C35	0.069 (4)	0.071 (4)	0.056 (4)	−0.034 (4)	−0.002 (3)	−0.026 (3)
C36	0.064 (4)	0.073 (5)	0.081 (4)	−0.026 (4)	0.024 (3)	−0.001 (4)

Co1—O3	1.887 (3)	C12—H12A	0.9300
Co1—O7	1.882 (3)	C13—C14	1.375 (7)
Co1—N3	1.917 (4)	C13—H13A	0.9300
Co1—N6	1.932 (4)	C14—H14A	0.9300
Co1—N7	1.983 (4)	C15—H15A	0.9600
Co1—Cl1	2.2472 (17)	C15—H15B	0.9600
O1—N1	1.213 (6)	C15—H15C	0.9600
O2—N1	1.221 (6)	C16—C17	1.384 (7)
O3—C7	1.281 (5)	C16—C21	1.387 (7)
O4—C10	1.367 (7)	C16—C22	1.507 (7)
O4—C15	1.445 (6)	C17—C18	1.371 (7)
O5—N4	1.235 (8)	C17—H17A	0.9300
O6—N4	1.218 (8)	C18—C19	1.353 (8)
O7—C22	1.298 (6)	C18—H18A	0.9300
O8—C25	1.346 (7)	C19—C20	1.374 (9)
O8—C30	1.424 (8)	C20—C21	1.371 (7)
N1—C4	1.467 (7)	C20—H20A	0.9300
N2—C7	1.311 (6)	C21—H21A	0.9300
N2—N3	1.395 (5)	C23—C24	1.450 (7)
N3—C8	1.304 (5)	C23—H23A	0.9300
N4—C19	1.470 (8)	C24—C29	1.400 (7)
N5—C22	1.326 (6)	C24—C25	1.408 (7)
N5—N6	1.390 (5)	C25—C26	1.393 (8)
N6—C23	1.294 (6)	C26—C27	1.387 (8)
N7—C35	1.332 (6)	C26—H26A	0.9300
N7—C31	1.336 (6)	C27—C28	1.357 (9)
C1—C2	1.388 (6)	C27—H27A	0.9300
C1—C6	1.392 (6)	C28—C29	1.394 (7)
C1—C7	1.487 (7)	C28—H28A	0.9300
C2—C3	1.374 (6)	C29—H29A	0.9300
C2—H2B	0.9300	C30—H30A	0.9600
C3—C4	1.385 (7)	C30—H30B	0.9600
C3—H3A	0.9300	C30—H30C	0.9600
C4—C5	1.365 (7)	C31—C32	1.374 (6)
C5—C6	1.362 (7)	C31—H31A	0.9300
C5—H5B	0.9300	C32—C33	1.374 (7)
C6—H6A	0.9300	C32—H32A	0.9300
C8—C9	1.456 (7)	C33—C34	1.381 (8)
C8—H8A	0.9300	C33—C36	1.524 (7)
C9—C14	1.395 (7)	C34—C35	1.385 (7)
C9—C10	1.424 (7)	C34—H34A	0.9300
C10—C11	1.364 (8)	C35—H35A	0.9300
C11—C12	1.381 (9)	C36—H36A	0.9600
C11—H11A	0.9300	C36—H36B	0.9600
C12—C13	1.393 (9)	C36—H36C	0.9600
O7—Co1—O3	173.83 (15)	C9—C14—H14A	119.1
O7—Co1—N3	93.09 (15)	O4—C15—H15A	109.5
O3—Co1—N3	82.36 (15)	O4—C15—H15B	109.5
O7—Co1—N6	82.64 (17)	H15A—C15—H15B	109.5
O3—Co1—N6	93.15 (17)	O4—C15—H15C	109.5
N3—Co1—N6	90.00 (16)	H15A—C15—H15C	109.5
O7—Co1—N7	93.80 (15)	H15B—C15—H15C	109.5
O3—Co1—N7	90.72 (15)	C17—C16—C21	119.4 (5)
N3—Co1—N7	173.07 (18)	C17—C16—C22	119.7 (5)
N6—Co1—N7	90.18 (16)	C21—C16—C22	120.9 (5)
O7—Co1—Cl1	91.96 (12)	C18—C17—C16	120.2 (6)
O3—Co1—Cl1	92.19 (11)	C18—C17—H17A	119.9
N3—Co1—Cl1	89.84 (13)	C16—C17—H17A	119.9
N6—Co1—Cl1	174.59 (14)	C19—C18—C17	119.5 (6)
N7—Co1—Cl1	90.63 (12)	C19—C18—H18A	120.2
C7—O3—Co1	110.7 (3)	C17—C18—H18A	120.2
C10—O4—C15	117.6 (5)	C18—C19—C20	121.8 (6)
C22—O7—Co1	110.5 (3)	C18—C19—N4	119.1 (7)
C25—O8—C30	119.5 (6)	C20—C19—N4	119.2 (7)
O1—N1—O2	122.7 (5)	C21—C20—C19	119.1 (6)
O1—N1—C4	118.8 (5)	C21—C20—H20A	120.5
O2—N1—C4	118.4 (5)	C19—C20—H20A	120.5
C7—N2—N3	108.7 (4)	C20—C21—C16	120.1 (6)
C8—N3—N2	119.5 (4)	C20—C21—H21A	120.0
C8—N3—Co1	127.2 (4)	C16—C21—H21A	120.0
N2—N3—Co1	113.3 (3)	O7—C22—N5	124.6 (5)
O6—N4—O5	124.6 (7)	O7—C22—C16	118.5 (5)
O6—N4—C19	119.2 (8)	N5—C22—C16	116.9 (5)
O5—N4—C19	116.2 (8)	N6—C23—C24	131.7 (5)
C22—N5—N6	108.6 (4)	N6—C23—H23A	114.1
C23—N6—N5	119.3 (5)	C24—C23—H23A	114.1
C23—N6—Co1	127.2 (4)	C29—C24—C25	118.4 (6)
N5—N6—Co1	113.5 (3)	C29—C24—C23	125.6 (5)
C35—N7—C31	116.7 (4)	C25—C24—C23	116.0 (5)
C35—N7—Co1	122.3 (4)	O8—C25—C26	123.5 (6)
C31—N7—Co1	121.0 (3)	O8—C25—C24	116.7 (6)
C2—C1—C6	119.7 (5)	C26—C25—C24	119.8 (6)
C2—C1—C7	119.2 (4)	C27—C26—C25	120.0 (6)
C6—C1—C7	121.2 (4)	C27—C26—H26A	120.0
C3—C2—C1	120.4 (5)	C25—C26—H26A	120.0
C3—C2—H2B	119.8	C28—C27—C26	121.1 (7)
C1—C2—H2B	119.8	C28—C27—H27A	119.5
C2—C3—C4	117.9 (5)	C26—C27—H27A	119.5
C2—C3—H3A	121.1	C27—C28—C29	119.8 (6)
C4—C3—H3A	121.1	C27—C28—H28A	120.1
C5—C4—C3	122.8 (5)	C29—C28—H28A	120.1
C5—C4—N1	118.1 (5)	C28—C29—C24	120.9 (6)
C3—C4—N1	119.1 (5)	C28—C29—H29A	119.6
C6—C5—C4	118.9 (5)	C24—C29—H29A	119.6
C6—C5—H5B	120.6	O8—C30—H30A	109.5
C4—C5—H5B	120.6	O8—C30—H30B	109.5
C5—C6—C1	120.4 (5)	H30A—C30—H30B	109.5
C5—C6—H6A	119.8	O8—C30—H30C	109.5
C1—C6—H6A	119.8	H30A—C30—H30C	109.5
O3—C7—N2	124.8 (5)	H30B—C30—H30C	109.5
O3—C7—C1	118.0 (4)	N7—C31—C32	123.4 (5)
N2—C7—C1	117.2 (4)	N7—C31—H31A	118.3
N3—C8—C9	129.8 (5)	C32—C31—H31A	118.3
N3—C8—H8A	115.1	C33—C32—C31	120.1 (5)
C9—C8—H8A	115.1	C33—C32—H32A	119.9
C14—C9—C10	117.3 (5)	C31—C32—H32A	119.9
C14—C9—C8	126.8 (5)	C32—C33—C34	116.8 (5)
C10—C9—C8	115.9 (5)	C32—C33—C36	121.6 (6)
C11—C10—O4	123.9 (6)	C34—C33—C36	121.6 (6)
C11—C10—C9	121.0 (6)	C33—C34—C35	119.9 (6)
O4—C10—C9	115.0 (5)	C33—C34—H34A	120.1
C10—C11—C12	120.1 (6)	C35—C34—H34A	120.1
C10—C11—H11A	120.0	N7—C35—C34	123.0 (5)
C12—C11—H11A	120.0	N7—C35—H35A	118.5
C11—C12—C13	120.6 (6)	C34—C35—H35A	118.5
C11—C12—H12A	119.7	C33—C36—H36A	109.5
C13—C12—H12A	119.7	C33—C36—H36B	109.5
C14—C13—C12	119.2 (6)	H36A—C36—H36B	109.5
C14—C13—H13A	120.4	C33—C36—H36C	109.5
C12—C13—H13A	120.4	H36A—C36—H36C	109.5
C13—C14—C9	121.8 (6)	H36B—C36—H36C	109.5
C13—C14—H14A	119.1
N3—Co1—O3—C7	2.5 (3)	C15—O4—C10—C9	175.4 (5)
N6—Co1—O3—C7	−87.1 (3)	C14—C9—C10—C11	−2.3 (8)
N7—Co1—O3—C7	−177.3 (3)	C8—C9—C10—C11	178.5 (5)
Cl1—Co1—O3—C7	92.1 (3)	C14—C9—C10—O4	−178.9 (5)
N3—Co1—O7—C22	−86.5 (3)	C8—C9—C10—O4	2.0 (7)
N6—Co1—O7—C22	3.1 (3)	O4—C10—C11—C12	178.1 (6)
N7—Co1—O7—C22	92.8 (3)	C9—C10—C11—C12	1.8 (9)
Cl1—Co1—O7—C22	−176.4 (3)	C10—C11—C12—C13	−0.6 (10)
C7—N2—N3—C8	−176.1 (4)	C11—C12—C13—C14	0.0 (11)
C7—N2—N3—Co1	2.8 (5)	C12—C13—C14—C9	−0.6 (11)
O7—Co1—N3—C8	−8.4 (4)	C10—C9—C14—C13	1.7 (9)
O3—Co1—N3—C8	175.8 (4)	C8—C9—C14—C13	−179.3 (6)
N6—Co1—N3—C8	−91.0 (4)	C21—C16—C17—C18	−0.1 (9)
Cl1—Co1—N3—C8	83.6 (4)	C22—C16—C17—C18	−178.0 (5)
O7—Co1—N3—N2	172.8 (3)	C16—C17—C18—C19	0.6 (9)
O3—Co1—N3—N2	−3.0 (3)	C17—C18—C19—C20	−0.3 (10)
Cl1—Co1—N3—N2	−95.2 (3)	C17—C18—C19—N4	−179.2 (6)
C22—N5—N6—C23	−179.7 (4)	O6—N4—C19—C18	10.4 (10)
C22—N5—N6—Co1	1.0 (4)	O5—N4—C19—C18	−170.5 (7)
O7—Co1—N6—C23	178.4 (4)	O6—N4—C19—C20	−168.5 (7)
O3—Co1—N6—C23	−6.1 (4)	O5—N4—C19—C20	10.6 (10)
N3—Co1—N6—C23	−88.5 (4)	C18—C19—C20—C21	−0.5 (10)
N7—Co1—N6—C23	84.6 (4)	N4—C19—C20—C21	178.4 (5)
O7—Co1—N6—N5	−2.3 (3)	C19—C20—C21—C16	1.0 (9)
O3—Co1—N6—N5	173.1 (3)	C17—C16—C21—C20	−0.7 (8)
N3—Co1—N6—N5	90.8 (3)	C22—C16—C21—C20	177.2 (5)
N7—Co1—N6—N5	−96.1 (3)	Co1—O7—C22—N5	−3.8 (5)
O7—Co1—N7—C35	0.5 (4)	Co1—O7—C22—C16	174.8 (3)
O3—Co1—N7—C35	176.3 (4)	N6—N5—C22—O7	1.9 (6)
N6—Co1—N7—C35	83.1 (4)	N6—N5—C22—C16	−176.8 (4)
Cl1—Co1—N7—C35	−91.5 (4)	C17—C16—C22—O7	−18.2 (7)
O7—Co1—N7—C31	−179.1 (4)	C21—C16—C22—O7	163.9 (5)
O3—Co1—N7—C31	−3.3 (4)	C17—C16—C22—N5	160.5 (5)
N6—Co1—N7—C31	−96.5 (4)	C21—C16—C22—N5	−17.4 (7)
Cl1—Co1—N7—C31	88.9 (4)	N5—N6—C23—C24	−3.0 (7)
C6—C1—C2—C3	−0.5 (8)	Co1—N6—C23—C24	176.2 (4)
C7—C1—C2—C3	177.6 (5)	N6—C23—C24—C29	1.5 (8)
C1—C2—C3—C4	0.0 (8)	N6—C23—C24—C25	−178.8 (5)
C2—C3—C4—C5	1.5 (9)	C30—O8—C25—C26	6.5 (9)
C2—C3—C4—N1	−178.0 (5)	C30—O8—C25—C24	−174.6 (6)
O1—N1—C4—C5	6.1 (9)	C29—C24—C25—O8	178.4 (5)
O2—N1—C4—C5	−176.1 (6)	C23—C24—C25—O8	−1.3 (7)
O1—N1—C4—C3	−174.3 (6)	C29—C24—C25—C26	−2.6 (7)
O2—N1—C4—C3	3.5 (9)	C23—C24—C25—C26	177.7 (5)
C3—C4—C5—C6	−2.5 (9)	O8—C25—C26—C27	−179.5 (5)
N1—C4—C5—C6	177.1 (5)	C24—C25—C26—C27	1.6 (8)
C4—C5—C6—C1	1.9 (8)	C25—C26—C27—C28	0.5 (9)
C2—C1—C6—C5	−0.4 (8)	C26—C27—C28—C29	−1.5 (9)
C7—C1—C6—C5	−178.5 (5)	C27—C28—C29—C24	0.5 (8)
Co1—O3—C7—N2	−1.8 (6)	C25—C24—C29—C28	1.6 (7)
Co1—O3—C7—C1	179.2 (3)	C23—C24—C29—C28	−178.7 (5)
N3—N2—C7—O3	−0.7 (7)	C35—N7—C31—C32	−2.6 (8)
N3—N2—C7—C1	178.4 (4)	Co1—N7—C31—C32	177.0 (4)
C2—C1—C7—O3	−2.3 (7)	N7—C31—C32—C33	2.1 (8)
C6—C1—C7—O3	175.7 (5)	C31—C32—C33—C34	−0.4 (8)
C2—C1—C7—N2	178.6 (5)	C31—C32—C33—C36	−178.6 (5)
C6—C1—C7—N2	−3.4 (7)	C32—C33—C34—C35	−0.7 (8)
N2—N3—C8—C9	−1.9 (8)	C36—C33—C34—C35	177.6 (5)
Co1—N3—C8—C9	179.3 (4)	C31—N7—C35—C34	1.5 (8)
N3—C8—C9—C14	4.1 (10)	Co1—N7—C35—C34	−178.1 (4)
N3—C8—C9—C10	−176.9 (5)	C33—C34—C35—N7	0.1 (9)
C15—O4—C10—C11	−1.0 (8)

Table 1

Selected bond lengths (Å)

Co1—O3	1.887 (3)
Co1—O7	1.882 (3)
Co1—N3	1.917 (4)
Co1—N6	1.932 (4)
Co1—N7	1.983 (4)
Co1—Cl1	2.2472 (17)