Bis{4-chloro-N'-[phen-yl(2-pyrid-yl)methyl-idene]benzohydrazidato-κN',O}cobalt(III) nitrate methanol disolvate.

In the title compound, [Co(C(19)H(13)ClN(3)O)(2)]NO(3)·2CH(3)OH, the central Co(III) atom in the cation is surrounded by two tridentate ligands in a distorted octa-hedral fashion by four N and two O atoms. Classical O-H⋯O hydrogen bonds link both methanol solvent mol-ecules with the nitrate anion.

Related literature

For related work on the mononuclear cobalt compound, see: Herchel & Boca (2005 ▶). For a din class="Chemical">metallic dicobalt(II) complex, see: Gavrilova et al. (2002 ▶). For a spin-crossover FeII complex, see: Wu et al. (2009 ▶).

Experimental

Crystal data

[Co(C19H13ClN3O)2]NO3·2CH4O

M = 854.57

Monoclinic,

a = 12.914 (8) Å

b = 17.423 (11) Å

c = 17.451 (11) Å

β = 93.031 (8)°

V = 3921 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.63 mm−1

T = 293 K

0.31 × 0.23 × 0.21 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: ψ scan (SADABS; Bruker, 1997 ▶) T min = 0.839, T max = 0.875

18168 measured reflections

6859 independent reflections

4829 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.156

S = 1.07

6859 reflections

516 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAIn class="Chemical">NT; 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: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810032241/si2285sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032241/si2285Isup2.hkl

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

[Co(C19H13ClN3O)2]NO3·2CH4O	F(000) = 1760
Mr = 854.57	Dx = 1.448 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.914 (8) Å	Cell parameters from 6478 reflections
b = 17.423 (11) Å	θ = 2.0–29.8°
c = 17.451 (11) Å	µ = 0.63 mm−1
β = 93.031 (8)°	T = 293 K
V = 3921 (4) Å3	Block, dark-red
Z = 4	0.31 × 0.23 × 0.21 mm

Bruker SMART APEXII CCD area-detector diffractometer	6859 independent reflections
Radiation source: fine-focus sealed tube	4829 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: ψ scan (SADABS; Bruker, 1997)	h = −15→13
Tmin = 0.839, Tmax = 0.875	k = −20→20
18168 measured reflections	l = −20→16

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0912P)2] where P = (Fo2 + 2Fc2)/3
6859 reflections	(Δ/σ)max < 0.001
516 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Experimental. The magnetic measurements were performed on Quantum Design SQUID, MPMS-5S magnetometer.

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
Co1	0.78242 (3)	0.67158 (2)	0.45385 (2)	0.03739 (16)
Cl1	1.25567 (8)	0.99362 (6)	0.58995 (7)	0.0794 (3)
C1	0.5964 (3)	0.5811 (2)	0.4093 (2)	0.0584 (10)
H1A	0.6374	0.5499	0.3801	0.070*
Cl2	0.87476 (11)	0.29952 (6)	0.76381 (6)	0.0893 (4)
C2	0.4924 (3)	0.5647 (3)	0.4130 (3)	0.0785 (13)
H2A	0.4635	0.5232	0.3860	0.094*
C3	0.4327 (3)	0.6090 (3)	0.4561 (3)	0.0953 (17)
H3A	0.3628	0.5976	0.4598	0.143*
C4	0.4764 (3)	0.6723 (2)	0.4953 (3)	0.0776 (13)
H4A	0.4359	0.7038	0.5246	0.093*
C5	0.5800 (3)	0.68681 (19)	0.4894 (2)	0.0499 (9)
C6	0.6359 (2)	0.75209 (18)	0.52701 (18)	0.0428 (8)
C7	0.5881 (2)	0.8070 (2)	0.5784 (2)	0.0494 (9)
C8	0.5451 (3)	0.7802 (3)	0.6441 (2)	0.0721 (12)
H8A	0.5458	0.7279	0.6551	0.087*
C9	0.5006 (4)	0.8317 (3)	0.6939 (3)	0.0941 (16)
H9A	0.4723	0.8140	0.7385	0.113*
C10	0.4986 (4)	0.9092 (3)	0.6767 (4)	0.0972 (18)
H10A	0.4676	0.9434	0.7093	0.117*
C11	0.5417 (3)	0.9353 (3)	0.6127 (3)	0.0810 (13)
H11A	0.5410	0.9876	0.6021	0.097*
C12	0.5867 (3)	0.8852 (2)	0.5631 (2)	0.0618 (10)
H12A	0.6161	0.9039	0.5193	0.074*
C13	0.8957 (2)	0.78507 (16)	0.51482 (16)	0.0357 (7)
C14	0.9853 (2)	0.83520 (16)	0.53516 (17)	0.0384 (7)
C15	0.9705 (3)	0.90836 (18)	0.5657 (2)	0.0473 (8)
H15A	0.9037	0.9249	0.5745	0.057*
C16	1.0538 (3)	0.95642 (19)	0.5829 (2)	0.0541 (9)
H16A	1.0436	1.0049	0.6035	0.065*
C17	1.1516 (3)	0.9312 (2)	0.5690 (2)	0.0532 (9)
C18	1.1684 (3)	0.8602 (2)	0.5394 (2)	0.0556 (9)
H18A	1.2355	0.8447	0.5301	0.067*
C19	1.0863 (3)	0.8113 (2)	0.5233 (2)	0.0501 (9)
H19A	1.0982	0.7624	0.5044	0.060*
C20	0.9368 (3)	0.47364 (19)	0.2934 (2)	0.0512 (9)
H20A	0.9804	0.4804	0.3370	0.061*
C21	0.9521 (3)	0.4125 (2)	0.2450 (3)	0.0675 (11)
H21A	1.0063	0.3784	0.2560	0.081*
C22	0.8877 (4)	0.4018 (2)	0.1807 (2)	0.0760 (13)
H22A	0.8986	0.3605	0.1483	0.091*
C23	0.8071 (4)	0.4517 (2)	0.1639 (2)	0.0698 (12)
H23A	0.7630	0.4439	0.1207	0.084*
C24	0.7922 (3)	0.5131 (2)	0.2112 (2)	0.0541 (9)
H24A	0.7385	0.5474	0.1994	0.065*
C25	0.8568 (2)	0.52489 (18)	0.27717 (17)	0.0408 (8)
C26	0.8359 (2)	0.59022 (17)	0.32795 (17)	0.0391 (7)
C27	0.8125 (2)	0.66884 (17)	0.29955 (17)	0.0406 (7)
C28	0.8283 (3)	0.69599 (19)	0.22675 (19)	0.0501 (9)
H28A	0.8529	0.6634	0.1896	0.060*
C29	0.8071 (3)	0.7723 (2)	0.2094 (2)	0.0594 (10)
H29A	0.8168	0.7909	0.1604	0.071*
C30	0.7716 (3)	0.8203 (2)	0.2648 (2)	0.0594 (10)
H30A	0.7573	0.8715	0.2537	0.071*
C31	0.7577 (3)	0.79147 (19)	0.3368 (2)	0.0526 (9)
H31A	0.7337	0.8238	0.3744	0.063*
C32	0.8300 (2)	0.53820 (17)	0.51756 (17)	0.0386 (7)
C33	0.8387 (2)	0.47777 (17)	0.57681 (17)	0.0373 (7)
C34	0.7889 (2)	0.48666 (18)	0.64438 (19)	0.0435 (8)
H34A	0.7487	0.5301	0.6514	0.052*
C35	0.7981 (3)	0.43203 (19)	0.7017 (2)	0.0512 (9)
H35A	0.7636	0.4383	0.7467	0.061*
C36	0.8591 (3)	0.36758 (19)	0.69139 (19)	0.0516 (9)
C37	0.9087 (3)	0.35630 (19)	0.6240 (2)	0.0504 (9)
H37A	0.9486	0.3126	0.6172	0.061*
C38	0.8977 (3)	0.41166 (17)	0.56659 (19)	0.0428 (8)
H38A	0.9301	0.4045	0.5208	0.051*
N1	0.6394 (2)	0.64084 (15)	0.44688 (15)	0.0445 (7)
N2	0.73280 (19)	0.75294 (13)	0.50965 (14)	0.0372 (6)
N3	0.80414 (19)	0.80719 (14)	0.53669 (14)	0.0390 (6)
N4	0.7780 (2)	0.71727 (15)	0.35430 (15)	0.0423 (6)
N5	0.83192 (19)	0.58678 (14)	0.40247 (14)	0.0388 (6)
N6	0.8493 (2)	0.52095 (14)	0.44585 (14)	0.0406 (6)
O1	0.91181 (16)	0.72240 (11)	0.47687 (12)	0.0416 (5)
O2	0.80192 (16)	0.60633 (11)	0.54059 (11)	0.0412 (5)
O39	0.3498 (5)	1.5978 (3)	0.6311 (3)	0.165 (2)
H39D	0.3843	1.6034	0.6715	0.248*
C39	0.2696 (5)	1.6509 (3)	0.6272 (4)	0.125 (2)
H39A	0.2975	1.7016	0.6341	0.187*
H39B	0.2228	1.6403	0.6669	0.187*
H39C	0.2329	1.6474	0.5781	0.187*
C40	0.3173 (11)	1.7336 (7)	0.8722 (10)	0.362 (12)
H40A	0.3084	1.7797	0.9011	0.543*
H40B	0.2507	1.7119	0.8580	0.543*
H40C	0.3529	1.7453	0.8267	0.543*
O40	0.3808 (7)	1.6761 (6)	0.9207 (6)	0.279 (4)
H40D	0.4158	1.6491	0.8909	0.419*
O3	0.4443 (5)	1.6345 (6)	0.7710 (5)	0.279 (5)
O4	0.5735 (5)	1.5770 (3)	0.7264 (4)	0.179 (3)
O5	0.5666 (5)	1.6126 (4)	0.8508 (4)	0.188 (3)
N7	0.5329 (5)	1.6068 (4)	0.7830 (5)	0.130 (2)

	U11	U22	U33	U12	U13	U23
Co1	0.0474 (3)	0.0359 (3)	0.0290 (3)	0.00039 (18)	0.00347 (18)	−0.00440 (17)
Cl1	0.0703 (7)	0.0821 (7)	0.0852 (8)	−0.0326 (6)	−0.0027 (6)	0.0005 (6)
C1	0.062 (2)	0.057 (2)	0.056 (2)	−0.0065 (18)	0.0029 (19)	−0.0148 (18)
Cl2	0.1574 (12)	0.0600 (6)	0.0515 (7)	0.0127 (7)	0.0158 (7)	0.0175 (5)
C2	0.062 (3)	0.081 (3)	0.093 (3)	−0.022 (2)	0.004 (2)	−0.033 (3)
C3	0.058 (3)	0.106 (4)	0.124 (5)	−0.025 (3)	0.017 (3)	−0.042 (3)
C4	0.054 (2)	0.084 (3)	0.096 (4)	−0.012 (2)	0.014 (2)	−0.029 (3)
C5	0.049 (2)	0.051 (2)	0.050 (2)	−0.0032 (16)	0.0047 (16)	−0.0083 (16)
C6	0.0439 (19)	0.0461 (19)	0.0386 (19)	0.0027 (15)	0.0043 (15)	−0.0054 (14)
C7	0.0401 (19)	0.058 (2)	0.051 (2)	0.0024 (16)	0.0030 (16)	−0.0157 (17)
C8	0.071 (3)	0.075 (3)	0.072 (3)	0.006 (2)	0.030 (2)	−0.006 (2)
C9	0.088 (4)	0.126 (5)	0.072 (3)	0.002 (3)	0.037 (3)	−0.025 (3)
C10	0.072 (3)	0.103 (4)	0.118 (5)	0.013 (3)	0.016 (3)	−0.055 (4)
C11	0.072 (3)	0.066 (3)	0.105 (4)	0.012 (2)	0.007 (3)	−0.025 (3)
C12	0.059 (2)	0.057 (2)	0.070 (3)	0.0083 (18)	0.008 (2)	−0.009 (2)
C13	0.0474 (19)	0.0366 (17)	0.0238 (16)	0.0003 (14)	0.0072 (14)	−0.0009 (13)
C14	0.0463 (18)	0.0422 (18)	0.0275 (16)	0.0000 (14)	0.0082 (14)	−0.0010 (13)
C15	0.051 (2)	0.0429 (19)	0.048 (2)	−0.0008 (15)	0.0092 (16)	−0.0030 (15)
C16	0.067 (2)	0.0420 (19)	0.053 (2)	−0.0088 (17)	0.0028 (19)	−0.0034 (16)
C17	0.058 (2)	0.060 (2)	0.043 (2)	−0.0198 (18)	0.0044 (17)	0.0017 (17)
C18	0.044 (2)	0.070 (2)	0.054 (2)	−0.0043 (18)	0.0075 (17)	−0.0018 (19)
C19	0.052 (2)	0.055 (2)	0.044 (2)	0.0008 (16)	0.0057 (16)	−0.0092 (16)
C20	0.056 (2)	0.050 (2)	0.047 (2)	0.0003 (17)	0.0032 (17)	−0.0118 (16)
C21	0.078 (3)	0.054 (2)	0.072 (3)	0.0069 (19)	0.019 (2)	−0.014 (2)
C22	0.123 (4)	0.051 (2)	0.055 (3)	−0.014 (3)	0.021 (3)	−0.023 (2)
C23	0.106 (3)	0.064 (3)	0.039 (2)	−0.016 (2)	−0.002 (2)	−0.0195 (19)
C24	0.072 (2)	0.052 (2)	0.038 (2)	−0.0066 (18)	−0.0035 (17)	−0.0052 (16)
C25	0.052 (2)	0.0423 (18)	0.0292 (17)	−0.0092 (15)	0.0079 (15)	−0.0073 (13)
C26	0.0453 (18)	0.0419 (18)	0.0302 (18)	−0.0010 (14)	0.0011 (14)	−0.0064 (13)
C27	0.0507 (19)	0.0435 (18)	0.0271 (17)	−0.0018 (14)	−0.0014 (14)	−0.0068 (13)
C28	0.072 (2)	0.048 (2)	0.0307 (19)	−0.0016 (17)	0.0037 (16)	−0.0064 (15)
C29	0.088 (3)	0.055 (2)	0.035 (2)	−0.0024 (19)	−0.0003 (19)	0.0044 (17)
C30	0.084 (3)	0.046 (2)	0.047 (2)	0.0085 (18)	0.000 (2)	0.0079 (17)
C31	0.073 (2)	0.045 (2)	0.041 (2)	0.0108 (17)	0.0037 (17)	−0.0017 (16)
C32	0.0461 (18)	0.0359 (17)	0.0339 (18)	−0.0040 (14)	0.0016 (14)	−0.0049 (13)
C33	0.0436 (18)	0.0383 (17)	0.0301 (17)	−0.0037 (13)	0.0015 (14)	−0.0062 (13)
C34	0.051 (2)	0.0398 (18)	0.0396 (19)	0.0005 (14)	0.0045 (15)	−0.0051 (14)
C35	0.068 (2)	0.051 (2)	0.036 (2)	−0.0028 (17)	0.0147 (17)	−0.0049 (16)
C36	0.078 (2)	0.0405 (19)	0.036 (2)	−0.0068 (17)	0.0023 (18)	0.0011 (15)
C37	0.067 (2)	0.0368 (18)	0.047 (2)	0.0045 (16)	0.0025 (18)	−0.0014 (15)
C38	0.054 (2)	0.0405 (18)	0.0342 (18)	−0.0029 (15)	0.0056 (15)	−0.0042 (14)
N1	0.0515 (16)	0.0400 (15)	0.0417 (16)	−0.0025 (12)	−0.0008 (13)	−0.0061 (12)
N2	0.0439 (16)	0.0364 (14)	0.0312 (15)	−0.0005 (11)	0.0014 (11)	−0.0027 (11)
N3	0.0439 (16)	0.0395 (14)	0.0340 (15)	−0.0017 (12)	0.0055 (12)	−0.0058 (11)
N4	0.0499 (16)	0.0430 (16)	0.0338 (15)	0.0029 (12)	0.0010 (12)	−0.0015 (12)
N5	0.0501 (16)	0.0365 (14)	0.0297 (15)	−0.0007 (11)	0.0018 (12)	−0.0017 (11)
N6	0.0547 (17)	0.0359 (14)	0.0313 (15)	0.0005 (12)	0.0023 (12)	−0.0033 (11)
O1	0.0467 (12)	0.0415 (12)	0.0370 (13)	0.0015 (9)	0.0051 (10)	−0.0085 (10)
O2	0.0580 (13)	0.0369 (12)	0.0291 (12)	0.0029 (10)	0.0052 (10)	−0.0041 (9)
O39	0.203 (5)	0.130 (4)	0.168 (5)	−0.012 (4)	0.056 (4)	−0.046 (3)
C39	0.120 (5)	0.086 (4)	0.173 (7)	0.009 (4)	0.054 (4)	−0.013 (4)
C40	0.288 (16)	0.233 (14)	0.54 (3)	0.011 (11)	−0.218 (17)	0.054 (16)
O40	0.248 (9)	0.326 (11)	0.263 (10)	−0.029 (7)	0.013 (7)	−0.119 (8)
O3	0.135 (5)	0.431 (12)	0.269 (9)	0.069 (6)	0.003 (5)	0.133 (9)
O4	0.156 (5)	0.140 (4)	0.245 (7)	−0.034 (3)	0.060 (5)	−0.033 (4)
O5	0.145 (5)	0.209 (6)	0.206 (7)	−0.063 (4)	−0.034 (4)	0.095 (5)
N7	0.088 (4)	0.115 (5)	0.188 (8)	−0.012 (3)	0.000 (5)	0.069 (5)

Co1—N2	1.853 (3)	C21—H21A	0.9300
Co1—N5	1.859 (3)	C22—C23	1.377 (6)
Co1—O2	1.899 (2)	C22—H22A	0.9300
Co1—N4	1.909 (3)	C23—C24	1.371 (5)
Co1—O1	1.915 (2)	C23—H23A	0.9300
Co1—N1	1.921 (3)	C24—C25	1.400 (5)
Cl1—C17	1.752 (3)	C24—H24A	0.9300
C1—N1	1.336 (4)	C25—C26	1.476 (4)
C1—C2	1.378 (5)	C26—N5	1.306 (4)
C1—H1A	0.9300	C26—C27	1.482 (4)
Cl2—C36	1.737 (3)	C27—N4	1.367 (4)
C2—C3	1.347 (6)	C27—C28	1.381 (5)
C2—H2A	0.9300	C28—C29	1.387 (5)
C3—C4	1.400 (6)	C28—H28A	0.9300
C3—H3A	0.9300	C29—C30	1.375 (5)
C4—C5	1.371 (5)	C29—H29A	0.9300
C4—H4A	0.9300	C30—C31	1.374 (5)
C5—N1	1.357 (4)	C30—H30A	0.9300
C5—C6	1.481 (4)	C31—N4	1.351 (4)
C6—N2	1.304 (4)	C31—H31A	0.9300
C6—C7	1.469 (4)	C32—O2	1.310 (3)
C7—C8	1.381 (5)	C32—N6	1.324 (4)
C7—C12	1.390 (5)	C32—C33	1.476 (4)
C8—C9	1.394 (6)	C33—C34	1.381 (4)
C8—H8A	0.9300	C33—C38	1.398 (4)
C9—C10	1.382 (7)	C34—C35	1.381 (5)
C9—H9A	0.9300	C34—H34A	0.9300
C10—C11	1.353 (7)	C35—C36	1.389 (5)
C10—H10A	0.9300	C35—H35A	0.9300
C11—C12	1.378 (5)	C36—C37	1.382 (5)
C11—H11A	0.9300	C37—C38	1.393 (4)
C12—H12A	0.9300	C37—H37A	0.9300
C13—O1	1.299 (3)	C38—H38A	0.9300
C13—N3	1.320 (4)	N2—N3	1.385 (3)
C13—C14	1.478 (4)	N5—N6	1.386 (3)
C14—C19	1.395 (5)	O39—C39	1.387 (7)
C14—C15	1.398 (4)	O39—H39D	0.8200
C15—C16	1.383 (5)	C39—H39A	0.9600
C15—H15A	0.9300	C39—H39B	0.9600
C16—C17	1.371 (5)	C39—H39C	0.9600
C16—H16A	0.9300	C40—O40	1.523 (12)
C17—C18	1.362 (5)	C40—H40A	0.9600
C18—C19	1.378 (5)	C40—H40B	0.9600
C18—H18A	0.9300	C40—H40C	0.9600
C19—H19A	0.9300	O40—H40D	0.8500
C20—C21	1.380 (5)	O3—N7	1.249 (7)
C20—C25	1.383 (5)	O4—N7	1.256 (8)
C20—H20A	0.9300	O5—N7	1.243 (8)
C21—C22	1.373 (6)
N2—Co1—N5	176.99 (11)	C24—C23—C22	119.5 (4)
N2—Co1—O2	94.25 (11)	C24—C23—H23A	120.2
N5—Co1—O2	82.78 (10)	C22—C23—H23A	120.2
N2—Co1—N4	99.48 (11)	C23—C24—C25	120.9 (4)
N5—Co1—N4	83.51 (11)	C23—C24—H24A	119.5
O2—Co1—N4	166.22 (10)	C25—C24—H24A	119.5
N2—Co1—O1	81.85 (10)	C20—C25—C24	118.6 (3)
N5—Co1—O1	98.64 (10)	C20—C25—C26	122.2 (3)
O2—Co1—O1	91.84 (9)	C24—C25—C26	119.1 (3)
N4—Co1—O1	88.96 (10)	N5—C26—C25	125.5 (3)
N2—Co1—N1	83.59 (11)	N5—C26—C27	111.0 (3)
N5—Co1—N1	95.86 (11)	C25—C26—C27	123.5 (3)
O2—Co1—N1	88.29 (10)	N4—C27—C28	120.1 (3)
N4—Co1—N1	94.38 (11)	N4—C27—C26	113.9 (3)
O1—Co1—N1	165.41 (10)	C28—C27—C26	126.0 (3)
N1—C1—C2	121.3 (3)	C27—C28—C29	119.5 (3)
N1—C1—H1A	119.4	C27—C28—H28A	120.3
C2—C1—H1A	119.4	C29—C28—H28A	120.3
C3—C2—C1	119.6 (4)	C30—C29—C28	119.9 (3)
C3—C2—H2A	120.2	C30—C29—H29A	120.0
C1—C2—H2A	120.2	C28—C29—H29A	120.0
C2—C3—C4	119.8 (4)	C31—C30—C29	119.0 (3)
C2—C3—H3A	120.1	C31—C30—H30A	120.5
C4—C3—H3A	120.1	C29—C30—H30A	120.5
C5—C4—C3	118.6 (4)	N4—C31—C30	121.5 (3)
C5—C4—H4A	120.7	N4—C31—H31A	119.2
C3—C4—H4A	120.7	C30—C31—H31A	119.2
N1—C5—C4	120.9 (3)	O2—C32—N6	124.4 (3)
N1—C5—C6	114.8 (3)	O2—C32—C33	116.3 (3)
C4—C5—C6	124.3 (3)	N6—C32—C33	119.3 (3)
N2—C6—C7	125.0 (3)	C34—C33—C38	118.9 (3)
N2—C6—C5	110.9 (3)	C34—C33—C32	119.8 (3)
C7—C6—C5	124.0 (3)	C38—C33—C32	121.4 (3)
C8—C7—C12	119.3 (3)	C35—C34—C33	121.0 (3)
C8—C7—C6	119.2 (3)	C35—C34—H34A	119.5
C12—C7—C6	121.5 (3)	C33—C34—H34A	119.5
C7—C8—C9	119.7 (4)	C34—C35—C36	119.4 (3)
C7—C8—H8A	120.1	C34—C35—H35A	120.3
C9—C8—H8A	120.1	C36—C35—H35A	120.3
C10—C9—C8	119.9 (5)	C37—C36—C35	121.1 (3)
C10—C9—H9A	120.1	C37—C36—Cl2	118.7 (3)
C8—C9—H9A	120.1	C35—C36—Cl2	120.2 (3)
C11—C10—C9	120.2 (4)	C36—C37—C38	118.6 (3)
C11—C10—H10A	119.9	C36—C37—H37A	120.7
C9—C10—H10A	119.9	C38—C37—H37A	120.7
C10—C11—C12	120.7 (4)	C37—C38—C33	121.0 (3)
C10—C11—H11A	119.6	C37—C38—H38A	119.5
C12—C11—H11A	119.6	C33—C38—H38A	119.5
C11—C12—C7	120.1 (4)	C1—N1—C5	119.8 (3)
C11—C12—H12A	119.9	C1—N1—Co1	128.4 (2)
C7—C12—H12A	119.9	C5—N1—Co1	111.7 (2)
O1—C13—N3	124.2 (3)	C6—N2—N3	123.9 (2)
O1—C13—C14	118.4 (3)	C6—N2—Co1	118.4 (2)
N3—C13—C14	117.4 (3)	N3—N2—Co1	117.31 (19)
C19—C14—C15	118.4 (3)	C13—N3—N2	107.0 (2)
C19—C14—C13	120.9 (3)	C31—N4—C27	120.0 (3)
C15—C14—C13	120.6 (3)	C31—N4—Co1	126.9 (2)
C16—C15—C14	121.0 (3)	C27—N4—Co1	112.5 (2)
C16—C15—H15A	119.5	C26—N5—N6	124.6 (3)
C14—C15—H15A	119.5	C26—N5—Co1	118.5 (2)
C17—C16—C15	118.7 (3)	N6—N5—Co1	116.38 (19)
C17—C16—H16A	120.6	C32—N6—N5	107.2 (2)
C15—C16—H16A	120.6	C13—O1—Co1	109.54 (19)
C18—C17—C16	121.6 (3)	C32—O2—Co1	108.96 (18)
C18—C17—Cl1	120.5 (3)	C39—O39—H39D	109.5
C16—C17—Cl1	117.9 (3)	O39—C39—H39A	109.5
C17—C18—C19	120.2 (3)	O39—C39—H39B	109.5
C17—C18—H18A	119.9	H39A—C39—H39B	109.5
C19—C18—H18A	119.9	O39—C39—H39C	109.5
C18—C19—C14	120.0 (3)	H39A—C39—H39C	109.5
C18—C19—H19A	120.0	H39B—C39—H39C	109.5
C14—C19—H19A	120.0	O40—C40—H40A	109.5
C21—C20—C25	120.2 (3)	O40—C40—H40B	109.5
C21—C20—H20A	119.9	H40A—C40—H40B	109.5
C25—C20—H20A	119.9	O40—C40—H40C	109.5
C22—C21—C20	120.3 (4)	H40A—C40—H40C	109.5
C22—C21—H21A	119.9	H40B—C40—H40C	109.5
C20—C21—H21A	119.9	C40—O40—H40D	108.1
C21—C22—C23	120.5 (4)	O5—N7—O3	113.6 (9)
C21—C22—H22A	119.8	O5—N7—O4	130.0 (8)
C23—C22—H22A	119.8	O3—N7—O4	116.4 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O39—H39D···O3	0.82	1.94	2.747 (11)	167.
O40—H40D···O3	0.85	2.16	2.873 (12)	142.
O40—H40D···O5	0.85	2.20	2.963 (12)	150.

Table 1

Selected bond lengths (Å)

Co1—N2	1.853 (3)
Co1—N5	1.859 (3)
Co1—O2	1.899 (2)
Co1—N4	1.909 (3)
Co1—O1	1.915 (2)
Co1—N1	1.921 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O39—H39D⋯O3	0.82	1.94	2.747 (11)	167
O40—H40D⋯O3	0.85	2.16	2.873 (12)	142
O40—H40D⋯O5	0.85	2.20	2.963 (12)	150