{2,2'-[o-Phenyl-enebis(nitrilo-methyl-idyne)]diphenolato}dipyridinecobalt(III) perchlorate.

The title compound, [Co(C(20)H(14)N(2)O(2))(C(5)H(5)N)(2)]ClO(4) or [Co(salophen)(py)(2)]ClO(4), where salophen is o-phenyl-enebis(nitrilo-methyl-idyne)]diphenolate and py is pyridine, contains a six-coordinate mononuclear cobalt(III) atom. The two phenolic O atoms and the two imine N atoms are located in cis positions. There are two pyridine mol-ecules attached to the metal atom, filling the axial sites with a mutually perpendicular disposition of the pyridine planes [86.11 (5)°]. The Co complexes are stacked in layers parallel to (100). Coherence of the structure is provided by a variety of C-H⋯O interactions between the complexes and the perchlor-ate counter anion.

Related literature

For general background to transition metal Schiff-base complexes with a tetra­dentate N2O2 ligand configuration, see: Schenk et al. (2007 ▶); Yamada (1999 ▶). For related Co complexes, see: Amirnasr et al. (2001 ▶); Khandar et al. (2007 ▶). For oxygenation and oxidation reactions of related Co complexes, see: Nishinaga & Tomita (1980 ▶); Park et al. (1998 ▶); Speiser & Stahl (1995 ▶). For the anti­microbial activity of related Co complexes, see: Kumar et al. (2009 ▶); Miodragović et al. (2006 ▶); Mishra et al. (2008 ▶).

Experimental

Crystal data

[Co(C20H14N2O2)(C5H5N)2]ClO4

M = 630.91

Monoclinic,

a = 33.4032 (16) Å

b = 10.6586 (5) Å

c = 16.3498 (8) Å

β = 112.179 (1)°

V = 5390.3 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.79 mm−1

T = 200 K

0.44 × 0.18 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.86, T max = 0.95

24638 measured reflections

7804 independent reflections

6268 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.086

S = 1.03

7804 reflections

379 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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 I, global. DOI: 10.1107/S1600536809027330/dn2470sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027330/dn2470Isup2.hkl

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

[Co(C20H14N2O2)(C5H5N)2]ClO4	F(000) = 2592
Mr = 630.91	Dx = 1.555 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9429 reflections
a = 33.4032 (16) Å	θ = 2.3–30.1°
b = 10.6586 (5) Å	µ = 0.79 mm−1
c = 16.3498 (8) Å	T = 200 K
β = 112.179 (1)°	Prism, brown
V = 5390.3 (4) Å3	0.44 × 0.18 × 0.07 mm
Z = 8

Bruker APEXII CCD diffractometer	7804 independent reflections
Radiation source: fine-focus sealed tube	6268 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 30.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −46→31
Tmin = 0.86, Tmax = 0.95	k = −14→14
24638 measured reflections	l = −22→22

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0413P)2 + 3.8856P] where P = (Fo2 + 2Fc2)/3
7804 reflections	(Δ/σ)max = 0.001
379 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

Experimental. Thin prisms from methanol. Bruker Kappa APEXII CCD diffractometer, full-sphere data collection. The temperature of 200 K was selected because crystals cracked at 100 K.

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	0.107115 (6)	0.532208 (17)	0.407335 (12)	0.02150 (6)
O1	0.05857 (3)	0.63179 (9)	0.39475 (7)	0.0278 (2)
O2	0.08497 (3)	0.42434 (10)	0.47107 (7)	0.0271 (2)
N1	0.12843 (4)	0.64456 (11)	0.34353 (8)	0.0235 (2)
N2	0.15559 (4)	0.43132 (11)	0.41820 (8)	0.0226 (2)
N3	0.14061 (4)	0.62115 (11)	0.51660 (8)	0.0253 (2)
N4	0.07267 (4)	0.44507 (11)	0.29606 (8)	0.0244 (2)
C1	0.05714 (5)	0.75357 (13)	0.38370 (10)	0.0264 (3)
C2	0.02490 (5)	0.82090 (15)	0.40153 (12)	0.0369 (4)
H2	0.0047	0.7764	0.4189	0.044*
C3	0.02208 (6)	0.94902 (16)	0.39429 (14)	0.0433 (4)
H3	0.0003	0.9918	0.4073	0.052*
C4	0.05072 (6)	1.01725 (16)	0.36813 (14)	0.0437 (4)
H4	0.0489	1.1061	0.3644	0.052*
C5	0.08176 (6)	0.95457 (15)	0.34766 (12)	0.0369 (3)
H5	0.1010	1.0010	0.3287	0.044*
C6	0.08562 (5)	0.82224 (13)	0.35431 (10)	0.0276 (3)
C7	0.11850 (5)	0.76275 (13)	0.33164 (9)	0.0265 (3)
H7	0.1341	0.8133	0.3061	0.032*
C8	0.16154 (4)	0.58912 (13)	0.32072 (9)	0.0243 (2)
C9	0.17806 (5)	0.63868 (15)	0.26110 (10)	0.0294 (3)
H9	0.1667	0.7144	0.2305	0.035*
C10	0.21117 (5)	0.57614 (16)	0.24715 (10)	0.0318 (3)
H10	0.2222	0.6081	0.2056	0.038*
C11	0.22845 (5)	0.46652 (15)	0.29348 (11)	0.0316 (3)
H11	0.2520	0.4264	0.2849	0.038*
C12	0.21183 (5)	0.41546 (15)	0.35168 (10)	0.0289 (3)
H12	0.2236	0.3403	0.3827	0.035*
C13	0.17757 (4)	0.47570 (13)	0.36432 (9)	0.0234 (2)
C14	0.16751 (5)	0.33115 (13)	0.46680 (9)	0.0251 (3)
H14	0.1938	0.2922	0.4708	0.030*
C15	0.14396 (5)	0.27522 (13)	0.51476 (9)	0.0263 (3)
C16	0.16013 (6)	0.16128 (15)	0.55987 (10)	0.0339 (3)
H16	0.1865	0.1283	0.5599	0.041*
C17	0.13848 (6)	0.09751 (16)	0.60357 (11)	0.0399 (4)
H17	0.1496	0.0208	0.6329	0.048*
C18	0.09986 (6)	0.14678 (16)	0.60434 (11)	0.0375 (3)
H18	0.0848	0.1031	0.6346	0.045*
C19	0.08332 (5)	0.25753 (15)	0.56190 (10)	0.0320 (3)
H19	0.0574	0.2902	0.5647	0.038*
C20	0.10420 (5)	0.32399 (13)	0.51409 (9)	0.0252 (3)
C21	0.12183 (5)	0.64920 (15)	0.57425 (10)	0.0321 (3)
H21	0.0938	0.6176	0.5640	0.039*
C22	0.14240 (6)	0.72265 (17)	0.64774 (11)	0.0385 (4)
H22	0.1286	0.7408	0.6876	0.046*
C23	0.18298 (6)	0.76947 (16)	0.66309 (11)	0.0373 (3)
H23	0.1972	0.8217	0.7127	0.045*
C24	0.20263 (5)	0.73919 (16)	0.60521 (11)	0.0352 (3)
H24	0.2308	0.7693	0.6147	0.042*
C25	0.18075 (5)	0.66448 (15)	0.53339 (10)	0.0299 (3)
H25	0.1946	0.6427	0.4942	0.036*
C26	0.07423 (5)	0.31985 (14)	0.28919 (10)	0.0301 (3)
H26	0.0932	0.2735	0.3381	0.036*
C27	0.04929 (6)	0.25592 (16)	0.21358 (11)	0.0377 (4)
H27	0.0513	0.1672	0.2106	0.045*
C28	0.02138 (5)	0.32254 (17)	0.14223 (11)	0.0373 (3)
H28	0.0036	0.2805	0.0899	0.045*
C29	0.01988 (5)	0.45122 (17)	0.14867 (11)	0.0357 (3)
H29	0.0013	0.4994	0.1004	0.043*
C30	0.04581 (5)	0.50935 (15)	0.22635 (10)	0.0309 (3)
H30	0.0445	0.5981	0.2305	0.037*
Cl1	0.203707 (13)	0.02747 (4)	0.38080 (2)	0.03354 (9)
O3	0.24141 (5)	0.10462 (14)	0.41527 (11)	0.0619 (4)
O4	0.16645 (5)	0.10872 (14)	0.34374 (11)	0.0570 (4)
O5	0.19906 (7)	−0.04830 (17)	0.44767 (11)	0.0740 (5)
O6	0.20593 (6)	−0.04926 (15)	0.31171 (11)	0.0634 (4)

	U11	U22	U33	U12	U13	U23
Co1	0.01951 (9)	0.02155 (9)	0.02323 (10)	−0.00096 (7)	0.00782 (7)	0.00160 (7)
O1	0.0234 (5)	0.0236 (4)	0.0379 (6)	0.0002 (4)	0.0133 (4)	0.0029 (4)
O2	0.0244 (5)	0.0270 (5)	0.0314 (5)	−0.0001 (4)	0.0122 (4)	0.0058 (4)
N1	0.0224 (5)	0.0250 (5)	0.0231 (5)	−0.0015 (4)	0.0086 (4)	0.0012 (4)
N2	0.0202 (5)	0.0240 (5)	0.0222 (5)	−0.0011 (4)	0.0066 (4)	−0.0006 (4)
N3	0.0261 (5)	0.0261 (5)	0.0240 (5)	−0.0002 (4)	0.0097 (4)	0.0004 (4)
N4	0.0198 (5)	0.0269 (5)	0.0251 (5)	−0.0012 (4)	0.0069 (4)	0.0010 (4)
C1	0.0236 (6)	0.0248 (6)	0.0294 (7)	0.0008 (5)	0.0085 (5)	0.0021 (5)
C2	0.0328 (8)	0.0305 (7)	0.0540 (10)	0.0039 (6)	0.0240 (7)	0.0056 (7)
C3	0.0427 (9)	0.0335 (8)	0.0627 (12)	0.0093 (7)	0.0300 (9)	0.0058 (8)
C4	0.0489 (10)	0.0247 (7)	0.0651 (12)	0.0060 (7)	0.0299 (9)	0.0058 (7)
C5	0.0384 (8)	0.0264 (6)	0.0504 (10)	0.0007 (6)	0.0219 (7)	0.0059 (7)
C6	0.0273 (7)	0.0244 (6)	0.0310 (7)	0.0007 (5)	0.0110 (5)	0.0036 (5)
C7	0.0272 (7)	0.0257 (6)	0.0267 (7)	−0.0022 (5)	0.0104 (5)	0.0034 (5)
C8	0.0217 (6)	0.0273 (6)	0.0236 (6)	−0.0029 (5)	0.0082 (5)	−0.0019 (5)
C9	0.0285 (7)	0.0333 (7)	0.0276 (7)	−0.0027 (5)	0.0121 (6)	0.0018 (6)
C10	0.0290 (7)	0.0414 (8)	0.0280 (7)	−0.0057 (6)	0.0142 (6)	−0.0028 (6)
C11	0.0261 (7)	0.0383 (8)	0.0328 (8)	−0.0014 (6)	0.0140 (6)	−0.0063 (6)
C12	0.0252 (6)	0.0312 (7)	0.0303 (7)	0.0006 (5)	0.0108 (5)	−0.0026 (6)
C13	0.0203 (6)	0.0269 (6)	0.0222 (6)	−0.0030 (5)	0.0070 (5)	−0.0035 (5)
C14	0.0227 (6)	0.0260 (6)	0.0228 (6)	0.0014 (5)	0.0042 (5)	−0.0005 (5)
C15	0.0281 (6)	0.0265 (6)	0.0213 (6)	−0.0001 (5)	0.0061 (5)	0.0012 (5)
C16	0.0394 (8)	0.0308 (7)	0.0278 (7)	0.0051 (6)	0.0083 (6)	0.0039 (6)
C17	0.0529 (10)	0.0299 (7)	0.0326 (8)	0.0018 (7)	0.0113 (7)	0.0095 (6)
C18	0.0451 (9)	0.0355 (8)	0.0298 (8)	−0.0089 (7)	0.0115 (7)	0.0069 (6)
C19	0.0314 (7)	0.0354 (7)	0.0281 (7)	−0.0051 (6)	0.0099 (6)	0.0052 (6)
C20	0.0264 (6)	0.0253 (6)	0.0212 (6)	−0.0042 (5)	0.0059 (5)	0.0011 (5)
C21	0.0325 (7)	0.0372 (8)	0.0300 (7)	0.0013 (6)	0.0158 (6)	0.0001 (6)
C22	0.0444 (9)	0.0448 (9)	0.0294 (8)	0.0056 (7)	0.0175 (7)	−0.0039 (6)
C23	0.0449 (9)	0.0350 (8)	0.0270 (7)	0.0012 (7)	0.0077 (6)	−0.0062 (6)
C24	0.0339 (8)	0.0372 (8)	0.0311 (7)	−0.0070 (6)	0.0084 (6)	−0.0053 (6)
C25	0.0283 (7)	0.0342 (7)	0.0275 (7)	−0.0040 (6)	0.0109 (6)	−0.0039 (6)
C26	0.0300 (7)	0.0273 (6)	0.0284 (7)	−0.0033 (6)	0.0059 (6)	0.0014 (5)
C27	0.0413 (9)	0.0313 (7)	0.0353 (8)	−0.0063 (6)	0.0086 (7)	−0.0048 (6)
C28	0.0306 (8)	0.0468 (8)	0.0287 (7)	−0.0050 (7)	0.0045 (6)	−0.0070 (6)
C29	0.0260 (7)	0.0476 (8)	0.0278 (7)	0.0061 (6)	0.0037 (6)	0.0016 (6)
C30	0.0271 (7)	0.0321 (7)	0.0302 (7)	0.0055 (6)	0.0069 (5)	0.0022 (5)
Cl1	0.0386 (2)	0.03535 (19)	0.02889 (18)	−0.00695 (15)	0.01530 (15)	−0.00310 (14)
O3	0.0448 (7)	0.0543 (8)	0.0685 (10)	−0.0165 (6)	0.0010 (7)	−0.0043 (7)
O4	0.0409 (7)	0.0565 (8)	0.0734 (10)	0.0025 (6)	0.0215 (7)	0.0056 (7)
O5	0.1066 (14)	0.0717 (11)	0.0531 (9)	−0.0091 (9)	0.0409 (10)	0.0203 (8)
O6	0.0824 (11)	0.0645 (9)	0.0529 (9)	−0.0057 (8)	0.0366 (8)	−0.0224 (7)

Co1—O2	1.8806 (10)	C12—C13	1.394 (2)
Co1—O1	1.8833 (10)	C12—H12	0.9500
Co1—N1	1.8947 (12)	C14—C15	1.433 (2)
Co1—N2	1.8953 (12)	C14—H14	0.9500
Co1—N3	1.9577 (12)	C15—C16	1.418 (2)
Co1—N4	1.9789 (12)	C15—C20	1.422 (2)
O1—C1	1.3089 (17)	C16—C17	1.373 (2)
O2—C20	1.3078 (17)	C16—H16	0.9500
N1—C7	1.2985 (18)	C17—C18	1.397 (3)
N1—C8	1.4222 (18)	C17—H17	0.9500
N2—C14	1.3004 (18)	C18—C19	1.375 (2)
N2—C13	1.4238 (18)	C18—H18	0.9500
N3—C25	1.3448 (19)	C19—C20	1.418 (2)
N3—C21	1.3484 (19)	C19—H19	0.9500
N4—C26	1.3420 (19)	C21—C22	1.380 (2)
N4—C30	1.3421 (19)	C21—H21	0.9500
C1—C2	1.413 (2)	C22—C23	1.376 (3)
C1—C6	1.420 (2)	C22—H22	0.9500
C2—C3	1.371 (2)	C23—C24	1.378 (2)
C2—H2	0.9500	C23—H23	0.9500
C3—C4	1.391 (3)	C24—C25	1.378 (2)
C3—H3	0.9500	C24—H24	0.9500
C4—C5	1.377 (2)	C25—H25	0.9500
C4—H4	0.9500	C26—C27	1.382 (2)
C5—C6	1.417 (2)	C26—H26	0.9500
C5—H5	0.9500	C27—C28	1.383 (2)
C6—C7	1.433 (2)	C27—H27	0.9500
C7—H7	0.9500	C28—C29	1.378 (3)
C8—C9	1.393 (2)	C28—H28	0.9500
C8—C13	1.403 (2)	C29—C30	1.384 (2)
C9—C10	1.382 (2)	C29—H29	0.9500
C9—H9	0.9500	C30—H30	0.9500
C10—C11	1.394 (2)	Cl1—O5	1.4142 (15)
C10—H10	0.9500	Cl1—O6	1.4190 (14)
C11—C12	1.382 (2)	Cl1—O3	1.4296 (14)
C11—H11	0.9500	Cl1—O4	1.4479 (15)
O2—Co1—O1	84.41 (4)	C11—C12—H12	120.4
O2—Co1—N1	178.39 (5)	C13—C12—H12	120.4
O1—Co1—N1	94.06 (5)	C12—C13—C8	119.92 (13)
O2—Co1—N2	95.85 (5)	C12—C13—N2	125.63 (13)
O1—Co1—N2	179.15 (5)	C8—C13—N2	114.44 (12)
N1—Co1—N2	85.69 (5)	N2—C14—C15	124.82 (13)
O2—Co1—N3	89.96 (5)	N2—C14—H14	117.6
O1—Co1—N3	89.93 (5)	C15—C14—H14	117.6
N1—Co1—N3	89.55 (5)	C16—C15—C20	119.23 (14)
N2—Co1—N3	90.89 (5)	C16—C15—C14	117.44 (14)
O2—Co1—N4	90.50 (5)	C20—C15—C14	123.19 (13)
O1—Co1—N4	89.22 (5)	C17—C16—C15	121.51 (16)
N1—Co1—N4	89.96 (5)	C17—C16—H16	119.2
N2—Co1—N4	89.97 (5)	C15—C16—H16	119.2
N3—Co1—N4	178.98 (5)	C16—C17—C18	119.21 (15)
C1—O1—Co1	123.99 (9)	C16—C17—H17	120.4
C20—O2—Co1	125.60 (9)	C18—C17—H17	120.4
C7—N1—C8	122.95 (12)	C19—C18—C17	120.97 (15)
C7—N1—Co1	124.59 (10)	C19—C18—H18	119.5
C8—N1—Co1	111.89 (9)	C17—C18—H18	119.5
C14—N2—C13	122.71 (12)	C18—C19—C20	121.28 (16)
C14—N2—Co1	125.23 (10)	C18—C19—H19	119.4
C13—N2—Co1	112.04 (9)	C20—C19—H19	119.4
C25—N3—C21	118.18 (13)	O2—C20—C19	117.45 (13)
C25—N3—Co1	122.34 (10)	O2—C20—C15	124.79 (13)
C21—N3—Co1	119.26 (10)	C19—C20—C15	117.74 (13)
C26—N4—C30	118.12 (13)	N3—C21—C22	121.62 (15)
C26—N4—Co1	121.08 (10)	N3—C21—H21	119.2
C30—N4—Co1	120.76 (10)	C22—C21—H21	119.2
O1—C1—C2	117.78 (13)	C23—C22—C21	119.79 (16)
O1—C1—C6	124.30 (13)	C23—C22—H22	120.1
C2—C1—C6	117.91 (13)	C21—C22—H22	120.1
C3—C2—C1	121.39 (15)	C22—C23—C24	118.79 (15)
C3—C2—H2	119.3	C22—C23—H23	120.6
C1—C2—H2	119.3	C24—C23—H23	120.6
C2—C3—C4	120.97 (16)	C25—C24—C23	118.93 (16)
C2—C3—H3	119.5	C25—C24—H24	120.5
C4—C3—H3	119.5	C23—C24—H24	120.5
C5—C4—C3	119.30 (15)	N3—C25—C24	122.65 (15)
C5—C4—H4	120.3	N3—C25—H25	118.7
C3—C4—H4	120.3	C24—C25—H25	118.7
C4—C5—C6	121.29 (15)	N4—C26—C27	122.41 (14)
C4—C5—H5	119.4	N4—C26—H26	118.8
C6—C5—H5	119.4	C27—C26—H26	118.8
C5—C6—C1	119.08 (14)	C26—C27—C28	119.22 (16)
C5—C6—C7	118.49 (14)	C26—C27—H27	120.4
C1—C6—C7	122.43 (13)	C28—C27—H27	120.4
N1—C7—C6	124.61 (13)	C29—C28—C27	118.61 (15)
N1—C7—H7	117.7	C29—C28—H28	120.7
C6—C7—H7	117.7	C27—C28—H28	120.7
C9—C8—C13	120.43 (13)	C28—C29—C30	119.17 (15)
C9—C8—N1	125.36 (13)	C28—C29—H29	120.4
C13—C8—N1	114.21 (12)	C30—C29—H29	120.4
C10—C9—C8	119.06 (14)	N4—C30—C29	122.47 (15)
C10—C9—H9	120.5	N4—C30—H30	118.8
C8—C9—H9	120.5	C29—C30—H30	118.8
C9—C10—C11	120.52 (14)	O5—Cl1—O6	109.89 (11)
C9—C10—H10	119.7	O5—Cl1—O3	111.16 (11)
C11—C10—H10	119.7	O6—Cl1—O3	110.03 (11)
C12—C11—C10	120.86 (14)	O5—Cl1—O4	109.71 (11)
C12—C11—H11	119.6	O6—Cl1—O4	107.85 (10)
C10—C11—H11	119.6	O3—Cl1—O4	108.12 (9)
C11—C12—C13	119.11 (14)
O2—Co1—O1—C1	153.07 (12)	C5—C6—C7—N1	172.43 (15)
N1—Co1—O1—C1	−26.44 (12)	C1—C6—C7—N1	−7.1 (2)
N3—Co1—O1—C1	63.11 (12)	C7—N1—C8—C9	−20.5 (2)
N4—Co1—O1—C1	−116.34 (12)	Co1—N1—C8—C9	167.85 (12)
O1—Co1—O2—C20	−173.59 (12)	C7—N1—C8—C13	159.31 (13)
N2—Co1—O2—C20	7.22 (12)	Co1—N1—C8—C13	−12.36 (14)
N3—Co1—O2—C20	−83.66 (12)	C13—C8—C9—C10	−1.6 (2)
N4—Co1—O2—C20	97.24 (12)	N1—C8—C9—C10	178.21 (13)
O1—Co1—N1—C7	21.49 (12)	C8—C9—C10—C11	−1.4 (2)
N2—Co1—N1—C7	−159.33 (12)	C9—C10—C11—C12	2.5 (2)
N3—Co1—N1—C7	−68.41 (12)	C10—C11—C12—C13	−0.6 (2)
N4—Co1—N1—C7	110.70 (12)	C11—C12—C13—C8	−2.4 (2)
O1—Co1—N1—C8	−167.01 (9)	C11—C12—C13—N2	176.48 (13)
N2—Co1—N1—C8	12.17 (9)	C9—C8—C13—C12	3.5 (2)
N3—Co1—N1—C8	103.10 (9)	N1—C8—C13—C12	−176.31 (12)
N4—Co1—N1—C8	−77.80 (9)	C9—C8—C13—N2	−175.50 (12)
O2—Co1—N2—C14	−7.55 (12)	N1—C8—C13—N2	4.70 (17)
N1—Co1—N2—C14	171.98 (12)	C14—N2—C13—C12	4.6 (2)
N3—Co1—N2—C14	82.50 (12)	Co1—N2—C13—C12	−173.76 (11)
N4—Co1—N2—C14	−98.05 (12)	C14—N2—C13—C8	−176.42 (12)
O2—Co1—N2—C13	170.81 (9)	Co1—N2—C13—C8	5.17 (14)
N1—Co1—N2—C13	−9.66 (9)	C13—N2—C14—C15	−173.08 (13)
N3—Co1—N2—C13	−99.15 (9)	Co1—N2—C14—C15	5.1 (2)
N4—Co1—N2—C13	80.30 (9)	N2—C14—C15—C16	175.93 (13)
O2—Co1—N3—C25	142.20 (12)	N2—C14—C15—C20	0.2 (2)
O1—Co1—N3—C25	−133.39 (12)	C20—C15—C16—C17	−0.6 (2)
N1—Co1—N3—C25	−39.34 (12)	C14—C15—C16—C17	−176.47 (15)
N2—Co1—N3—C25	46.35 (12)	C15—C16—C17—C18	−0.7 (3)
O2—Co1—N3—C21	−43.24 (12)	C16—C17—C18—C19	0.2 (3)
O1—Co1—N3—C21	41.17 (12)	C17—C18—C19—C20	1.6 (2)
N1—Co1—N3—C21	135.23 (12)	Co1—O2—C20—C19	177.06 (10)
N2—Co1—N3—C21	−139.09 (12)	Co1—O2—C20—C15	−4.4 (2)
O2—Co1—N4—C26	−51.73 (12)	C18—C19—C20—O2	175.84 (14)
O1—Co1—N4—C26	−136.13 (12)	C18—C19—C20—C15	−2.8 (2)
N1—Co1—N4—C26	129.81 (12)	C16—C15—C20—O2	−176.25 (14)
N2—Co1—N4—C26	44.12 (12)	C14—C15—C20—O2	−0.6 (2)
O2—Co1—N4—C30	125.70 (12)	C16—C15—C20—C19	2.3 (2)
O1—Co1—N4—C30	41.29 (12)	C14—C15—C20—C19	177.89 (13)
N1—Co1—N4—C30	−52.76 (12)	C25—N3—C21—C22	1.5 (2)
N2—Co1—N4—C30	−138.45 (12)	Co1—N3—C21—C22	−173.33 (12)
Co1—O1—C1—C2	−161.34 (12)	N3—C21—C22—C23	0.3 (3)
Co1—O1—C1—C6	19.2 (2)	C21—C22—C23—C24	−1.5 (3)
O1—C1—C2—C3	177.90 (17)	C22—C23—C24—C25	0.8 (3)
C6—C1—C2—C3	−2.6 (3)	C21—N3—C25—C24	−2.1 (2)
C1—C2—C3—C4	0.7 (3)	Co1—N3—C25—C24	172.49 (12)
C2—C3—C4—C5	1.2 (3)	C23—C24—C25—N3	1.0 (3)
C3—C4—C5—C6	−1.2 (3)	C30—N4—C26—C27	−0.1 (2)
C4—C5—C6—C1	−0.7 (3)	Co1—N4—C26—C27	177.38 (13)
C4—C5—C6—C7	179.73 (17)	N4—C26—C27—C28	−0.5 (3)
O1—C1—C6—C5	−177.95 (15)	C26—C27—C28—C29	0.9 (3)
C2—C1—C6—C5	2.6 (2)	C27—C28—C29—C30	−0.8 (3)
O1—C1—C6—C7	1.6 (2)	C26—N4—C30—C29	0.2 (2)
C2—C1—C6—C7	−177.91 (15)	Co1—N4—C30—C29	−177.29 (12)
C8—N1—C7—C6	−179.53 (13)	C28—C29—C30—N4	0.3 (3)
Co1—N1—C7—C6	−8.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4i	0.95	2.40	3.293 (3)	157
C11—H11···O6ii	0.95	2.49	3.261 (3)	138
C12—H12···O3	0.95	2.59	3.501 (2)	161
C14—H14···O3iii	0.95	2.51	3.002 (2)	112
C29—H29···O1iv	0.95	2.47	3.111 (2)	124

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O4i	0.95	2.40	3.293 (3)	157
C11—H11⋯O6ii	0.95	2.49	3.261 (3)	138
C12—H12⋯O3	0.95	2.59	3.501 (2)	161
C14—H14⋯O3iii	0.95	2.51	3.002 (2)	112
C29—H29⋯O1iv	0.95	2.47	3.111 (2)	124

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .