Bis(2,2'-bipyridine-κN,N')(3,5-dinitro-2-oxidobenzoato-κO,O)cobalt(II).

In the title compound, [Co(C(7)H(2)N(2)O(7))(C(10)H(8)N(2))(2)], the Co(II) atom is coordinated by four N atoms from two 2,2'-bipyridine ligands and two O atoms from a 3,5-dinitro-2-oxidobenzoate ligand, displaying a distorted octa-hedral coordination geometry. The crystal structure involves C-H⋯O hydrogen bonds between the 2,2'-bipyridine ligands and the carboxyl-ate and NO(2) groups of the 3,5-dinitro-2-oxidobenzoate ligand.

Related literature

For general background, see: Lemoine et al. (2004 ▶); Wen et al. (2007a ▶,b ▶); Wen & Xie (2007 ▶); Yin et al. (2004 ▶). For related structures, see: Wen et al. (2007c ▶,d ▶); Wen & Liu (2007 ▶).

Experimental

Crystal data

[Co(C7H2N2O7)(C10H8N2)2]

M = 597.40

Monoclinic,

a = 8.103 (3) Å

b = 21.767 (7) Å

c = 14.335 (4) Å

β = 95.804 (13)°

V = 2515.4 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.74 mm−1

T = 293 (2) K

0.22 × 0.20 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: none

19627 measured reflections

4427 independent reflections

2952 reflections with I > 2σ(I)

R int = 0.080

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.090

S = 1.02

4427 reflections

370 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.31 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808041974/hy2168sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041974/hy2168Isup2.hkl

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

[Co(C7H2N2O7)(C10H8N2)2]	F(000) = 1220
Mr = 597.40	Dx = 1.578 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4427 reflections
a = 8.103 (3) Å	θ = 3.0–25.0°
b = 21.767 (7) Å	µ = 0.74 mm−1
c = 14.335 (4) Å	T = 293 K
β = 95.804 (13)°	Block, brown
V = 2515.4 (15) Å3	0.22 × 0.20 × 0.18 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	2952 reflections with I > 2σ(I)
Radiation source: 18 kW rotating anode	Rint = 0.080
graphite	θmax = 25.0°, θmin = 3.0°
ω scans	h = −9→9
19627 measured reflections	k = −25→25
4427 independent reflections	l = −17→15

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0295P)2 + 0.2101P] where P = (Fo2 + 2Fc2)/3
4427 reflections	(Δ/σ)max = 0.001
370 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

	x	y	z	Uiso*/Ueq
Co1	0.63835 (5)	0.37028 (2)	0.82451 (3)	0.03493 (13)
N1	0.4828 (4)	0.32130 (14)	0.51277 (18)	0.0486 (7)
N2	0.7733 (4)	0.49718 (17)	0.4014 (2)	0.0556 (8)
N3	0.5787 (3)	0.27604 (12)	0.84364 (17)	0.0406 (6)
N4	0.8319 (3)	0.32190 (13)	0.76558 (16)	0.0402 (7)
N5	0.4405 (3)	0.40721 (12)	0.89234 (16)	0.0380 (6)
N6	0.7350 (3)	0.37120 (13)	0.96914 (16)	0.0406 (6)
O1	0.6901 (4)	0.54777 (12)	0.73884 (16)	0.0853 (10)
O2	0.7262 (3)	0.45655 (10)	0.80574 (13)	0.0448 (6)
O3	0.5155 (3)	0.37447 (11)	0.69267 (13)	0.0433 (5)
O4	0.3629 (3)	0.30618 (14)	0.55073 (18)	0.0773 (9)
O5	0.5399 (3)	0.28916 (14)	0.4535 (2)	0.0791 (9)
O6	0.7632 (4)	0.47298 (14)	0.32404 (17)	0.0844 (9)
O7	0.8431 (4)	0.54639 (15)	0.41780 (19)	0.0820 (9)
C1	0.6593 (4)	0.46131 (15)	0.63950 (19)	0.0380 (8)
C2	0.5739 (3)	0.40396 (15)	0.62656 (19)	0.0346 (7)
C3	0.5590 (3)	0.38110 (15)	0.53228 (19)	0.0366 (8)
C4	0.6228 (4)	0.41067 (17)	0.4597 (2)	0.0431 (8)
H4A	0.6122	0.3937	0.3998	0.052*
C5	0.7027 (4)	0.46570 (16)	0.4764 (2)	0.0414 (8)
C6	0.7186 (4)	0.49101 (16)	0.5656 (2)	0.0439 (8)
H6A	0.7705	0.5289	0.5755	0.053*
C7	0.6922 (5)	0.49138 (17)	0.7350 (2)	0.0487 (9)
C8	0.4572 (4)	0.25584 (18)	0.8922 (2)	0.0540 (9)
H8A	0.3815	0.2843	0.9110	0.065*
C9	0.4385 (5)	0.19578 (19)	0.9155 (3)	0.0603 (10)
H9A	0.3536	0.1836	0.9505	0.072*
C10	0.5475 (5)	0.15383 (18)	0.8863 (3)	0.0616 (11)
H10A	0.5373	0.1125	0.9011	0.074*
C11	0.6722 (4)	0.17293 (17)	0.8349 (2)	0.0527 (9)
H11A	0.7462	0.1447	0.8138	0.063*
C12	0.6856 (4)	0.23450 (15)	0.8153 (2)	0.0393 (8)
C13	0.8198 (4)	0.26042 (16)	0.7643 (2)	0.0390 (8)
C14	0.9282 (5)	0.2248 (2)	0.7189 (3)	0.0665 (11)
H14A	0.9184	0.1822	0.7182	0.080*
C15	1.0509 (6)	0.2531 (2)	0.6748 (3)	0.0821 (14)
H15A	1.1246	0.2298	0.6438	0.098*
C16	1.0640 (5)	0.3156 (2)	0.6767 (3)	0.0697 (12)
H16A	1.1474	0.3354	0.6483	0.084*
C17	0.9511 (4)	0.34852 (18)	0.7214 (2)	0.0502 (9)
H17A	0.9576	0.3912	0.7211	0.060*
C18	0.2951 (4)	0.42475 (16)	0.8493 (2)	0.0488 (9)
H18A	0.2756	0.4195	0.7848	0.059*
C19	0.1727 (4)	0.45027 (18)	0.8965 (3)	0.0586 (10)
H19A	0.0719	0.4620	0.8647	0.070*
C20	0.2032 (5)	0.45792 (19)	0.9916 (3)	0.0638 (11)
H20A	0.1223	0.4750	1.0252	0.077*
C21	0.3512 (4)	0.44060 (17)	1.0369 (2)	0.0521 (9)
H21A	0.3724	0.4457	1.1015	0.063*
C22	0.4693 (4)	0.41536 (14)	0.98594 (19)	0.0379 (8)
C23	0.6354 (4)	0.39596 (15)	1.02814 (19)	0.0404 (8)
C24	0.6875 (5)	0.40303 (18)	1.1225 (2)	0.0591 (10)
H24A	0.6175	0.4207	1.1626	0.071*
C25	0.8424 (6)	0.3838 (2)	1.1559 (3)	0.0773 (14)
H25A	0.8798	0.3890	1.2190	0.093*
C26	0.9425 (5)	0.3570 (2)	1.0962 (3)	0.0695 (12)
H26A	1.0473	0.3426	1.1181	0.083*
C27	0.8848 (4)	0.35174 (17)	1.0030 (2)	0.0538 (10)
H27A	0.9530	0.3339	0.9621	0.065*

	U11	U22	U33	U12	U13	U23
Co1	0.0425 (2)	0.0350 (3)	0.0287 (2)	0.0003 (2)	0.01106 (17)	−0.0013 (2)
N1	0.0501 (17)	0.058 (2)	0.0394 (15)	−0.0070 (15)	0.0118 (14)	−0.0117 (15)
N2	0.074 (2)	0.058 (2)	0.0390 (17)	0.0131 (18)	0.0248 (16)	0.0142 (16)
N3	0.0478 (16)	0.0348 (17)	0.0400 (14)	−0.0024 (13)	0.0090 (13)	−0.0019 (13)
N4	0.0391 (15)	0.0479 (19)	0.0350 (13)	0.0013 (13)	0.0109 (12)	−0.0020 (13)
N5	0.0447 (15)	0.0381 (17)	0.0330 (13)	0.0002 (12)	0.0134 (12)	−0.0013 (12)
N6	0.0463 (16)	0.0409 (17)	0.0352 (13)	−0.0016 (14)	0.0068 (12)	0.0006 (13)
O1	0.181 (3)	0.0328 (17)	0.0465 (14)	−0.0150 (18)	0.0308 (17)	−0.0052 (12)
O2	0.0609 (14)	0.0401 (14)	0.0334 (11)	−0.0088 (12)	0.0056 (11)	−0.0045 (10)
O3	0.0481 (12)	0.0498 (15)	0.0329 (11)	−0.0093 (12)	0.0087 (10)	0.0011 (11)
O4	0.0691 (17)	0.096 (3)	0.0724 (17)	−0.0359 (16)	0.0336 (15)	−0.0251 (16)
O5	0.084 (2)	0.073 (2)	0.0871 (19)	−0.0207 (16)	0.0400 (17)	−0.0407 (17)
O6	0.134 (3)	0.087 (2)	0.0378 (13)	−0.0046 (19)	0.0406 (16)	0.0051 (15)
O7	0.120 (3)	0.065 (2)	0.0671 (17)	−0.0198 (19)	0.0384 (17)	0.0127 (16)
C1	0.0483 (19)	0.036 (2)	0.0308 (15)	0.0044 (16)	0.0119 (14)	0.0000 (14)
C2	0.0349 (17)	0.039 (2)	0.0307 (15)	0.0061 (15)	0.0075 (14)	0.0022 (14)
C3	0.0349 (16)	0.044 (2)	0.0322 (15)	0.0040 (15)	0.0074 (13)	−0.0035 (15)
C4	0.0462 (19)	0.056 (2)	0.0289 (15)	0.0142 (17)	0.0099 (15)	0.0000 (16)
C5	0.050 (2)	0.045 (2)	0.0314 (16)	0.0123 (17)	0.0154 (15)	0.0075 (15)
C6	0.057 (2)	0.036 (2)	0.0407 (18)	0.0039 (16)	0.0148 (16)	0.0030 (15)
C7	0.075 (2)	0.036 (2)	0.0376 (18)	−0.0123 (19)	0.0200 (18)	−0.0043 (17)
C8	0.052 (2)	0.050 (3)	0.064 (2)	−0.0062 (18)	0.0217 (19)	0.0009 (19)
C9	0.057 (2)	0.054 (3)	0.072 (2)	−0.016 (2)	0.017 (2)	0.005 (2)
C10	0.064 (3)	0.040 (2)	0.078 (3)	−0.011 (2)	−0.001 (2)	0.012 (2)
C11	0.052 (2)	0.037 (2)	0.067 (2)	0.0040 (17)	−0.0032 (19)	−0.0035 (19)
C12	0.0463 (19)	0.036 (2)	0.0348 (16)	0.0023 (16)	−0.0007 (15)	−0.0042 (15)
C13	0.0413 (18)	0.042 (2)	0.0342 (16)	0.0051 (16)	0.0073 (15)	−0.0038 (16)
C14	0.082 (3)	0.051 (3)	0.072 (2)	0.012 (2)	0.033 (2)	−0.009 (2)
C15	0.093 (3)	0.071 (3)	0.092 (3)	0.018 (3)	0.057 (3)	−0.008 (3)
C16	0.066 (3)	0.073 (3)	0.077 (3)	0.002 (2)	0.044 (2)	−0.001 (2)
C17	0.052 (2)	0.051 (2)	0.0510 (19)	−0.0008 (17)	0.0215 (18)	0.0010 (17)
C18	0.049 (2)	0.053 (2)	0.0446 (18)	0.0058 (18)	0.0074 (17)	−0.0025 (17)
C19	0.046 (2)	0.060 (3)	0.071 (2)	0.0125 (19)	0.0112 (19)	−0.006 (2)
C20	0.062 (3)	0.060 (3)	0.074 (3)	0.008 (2)	0.033 (2)	−0.015 (2)
C21	0.064 (2)	0.051 (3)	0.0445 (18)	0.0018 (19)	0.0237 (18)	−0.0062 (17)
C22	0.052 (2)	0.0319 (19)	0.0329 (15)	−0.0045 (15)	0.0177 (15)	−0.0032 (14)
C23	0.060 (2)	0.0330 (19)	0.0294 (15)	−0.0070 (16)	0.0102 (16)	0.0016 (14)
C24	0.084 (3)	0.060 (3)	0.0338 (17)	−0.003 (2)	0.0084 (19)	−0.0005 (18)
C25	0.102 (3)	0.087 (4)	0.039 (2)	0.001 (3)	−0.011 (2)	0.005 (2)
C26	0.071 (3)	0.077 (3)	0.056 (2)	0.009 (2)	−0.012 (2)	0.013 (2)
C27	0.051 (2)	0.062 (3)	0.0471 (19)	0.0014 (18)	0.0008 (17)	0.0042 (18)

Co1—O2	2.036 (2)	C8—H8A	0.9300
Co1—O3	2.047 (2)	C9—C10	1.365 (5)
Co1—N5	2.116 (2)	C9—H9A	0.9300
Co1—N3	2.132 (3)	C10—C11	1.373 (5)
Co1—N4	2.133 (3)	C10—H10A	0.9300
Co1—N6	2.141 (2)	C11—C12	1.376 (5)
N1—O4	1.206 (3)	C11—H11A	0.9300
N1—O5	1.227 (3)	C12—C13	1.482 (4)
N1—C3	1.456 (4)	C13—C14	1.382 (5)
N2—O6	1.223 (4)	C14—C15	1.377 (6)
N2—O7	1.223 (4)	C14—H14A	0.9300
N2—C5	1.441 (4)	C15—C16	1.365 (6)
N3—C8	1.336 (4)	C15—H15A	0.9300
N3—C12	1.343 (4)	C16—C17	1.370 (5)
N4—C17	1.339 (4)	C16—H16A	0.9300
N4—C13	1.342 (4)	C17—H17A	0.9300
N5—C18	1.329 (4)	C18—C19	1.373 (5)
N5—C22	1.350 (3)	C18—H18A	0.9300
N6—C27	1.330 (4)	C19—C20	1.371 (5)
N6—C23	1.340 (4)	C19—H19A	0.9300
O1—C7	1.229 (4)	C20—C21	1.359 (5)
O2—C7	1.274 (4)	C20—H20A	0.9300
O3—C2	1.275 (3)	C21—C22	1.376 (4)
C1—C6	1.369 (4)	C21—H21A	0.9300
C1—C2	1.430 (4)	C22—C23	1.480 (4)
C1—C7	1.516 (4)	C23—C24	1.384 (4)
C2—C3	1.434 (4)	C24—C25	1.364 (5)
C3—C4	1.369 (4)	C24—H24A	0.9300
C4—C5	1.371 (5)	C25—C26	1.369 (6)
C4—H4A	0.9300	C25—H25A	0.9300
C5—C6	1.387 (4)	C26—C27	1.375 (5)
C6—H6A	0.9300	C26—H26A	0.9300
C8—C9	1.362 (5)	C27—H27A	0.9300
O2—Co1—O3	88.90 (8)	C9—C8—H8A	118.3
O2—Co1—N5	90.10 (10)	C8—C9—C10	118.4 (4)
O3—Co1—N5	95.00 (9)	C8—C9—H9A	120.8
O2—Co1—N3	172.56 (10)	C10—C9—H9A	120.8
O3—Co1—N3	93.79 (9)	C9—C10—C11	119.7 (4)
N5—Co1—N3	96.56 (10)	C9—C10—H10A	120.1
O2—Co1—N4	97.01 (10)	C11—C10—H10A	120.1
O3—Co1—N4	87.98 (9)	C10—C11—C12	118.8 (4)
N5—Co1—N4	172.36 (11)	C10—C11—H11A	120.6
N3—Co1—N4	76.19 (11)	C12—C11—H11A	120.6
O2—Co1—N6	91.19 (9)	N3—C12—C11	121.8 (3)
O3—Co1—N6	171.78 (10)	N3—C12—C13	114.9 (3)
N5—Co1—N6	76.78 (10)	C11—C12—C13	123.3 (3)
N3—Co1—N6	87.14 (10)	N4—C13—C14	121.1 (3)
N4—Co1—N6	100.17 (10)	N4—C13—C12	115.4 (3)
O4—N1—O5	122.3 (3)	C14—C13—C12	123.5 (3)
O4—N1—C3	120.2 (3)	C15—C14—C13	119.2 (4)
O5—N1—C3	117.4 (3)	C15—C14—H14A	120.4
O6—N2—O7	122.6 (3)	C13—C14—H14A	120.4
O6—N2—C5	118.5 (4)	C16—C15—C14	119.7 (4)
O7—N2—C5	118.9 (3)	C16—C15—H15A	120.2
C8—N3—C12	117.9 (3)	C14—C15—H15A	120.2
C8—N3—Co1	124.9 (2)	C15—C16—C17	118.4 (4)
C12—N3—Co1	116.6 (2)	C15—C16—H16A	120.8
C17—N4—C13	118.7 (3)	C17—C16—H16A	120.8
C17—N4—Co1	124.6 (3)	N4—C17—C16	122.8 (4)
C13—N4—Co1	116.2 (2)	N4—C17—H17A	118.6
C18—N5—C22	118.6 (3)	C16—C17—H17A	118.6
C18—N5—Co1	125.0 (2)	N5—C18—C19	122.6 (3)
C22—N5—Co1	116.3 (2)	N5—C18—H18A	118.7
C27—N6—C23	118.9 (3)	C19—C18—H18A	118.7
C27—N6—Co1	125.5 (2)	C20—C19—C18	118.2 (3)
C23—N6—Co1	115.5 (2)	C20—C19—H19A	120.9
C7—O2—Co1	127.1 (2)	C18—C19—H19A	120.9
C2—O3—Co1	121.76 (18)	C21—C20—C19	120.2 (3)
C6—C1—C2	121.0 (3)	C21—C20—H20A	119.9
C6—C1—C7	116.8 (3)	C19—C20—H20A	119.9
C2—C1—C7	122.2 (3)	C20—C21—C22	119.0 (3)
O3—C2—C1	123.7 (3)	C20—C21—H21A	120.5
O3—C2—C3	121.6 (3)	C22—C21—H21A	120.5
C1—C2—C3	114.8 (3)	N5—C22—C21	121.4 (3)
C4—C3—C2	123.5 (3)	N5—C22—C23	115.3 (3)
C4—C3—N1	117.4 (3)	C21—C22—C23	123.3 (3)
C2—C3—N1	119.0 (3)	N6—C23—C24	121.2 (3)
C3—C4—C5	119.0 (3)	N6—C23—C22	115.9 (2)
C3—C4—H4A	120.5	C24—C23—C22	122.8 (3)
C5—C4—H4A	120.5	C25—C24—C23	119.2 (4)
C4—C5—C6	120.4 (3)	C25—C24—H24A	120.4
C4—C5—N2	120.0 (3)	C23—C24—H24A	120.4
C6—C5—N2	119.5 (3)	C24—C25—C26	119.5 (3)
C1—C6—C5	121.3 (3)	C24—C25—H25A	120.2
C1—C6—H6A	119.4	C26—C25—H25A	120.2
C5—C6—H6A	119.4	C25—C26—C27	118.6 (4)
O1—C7—O2	124.2 (3)	C25—C26—H26A	120.7
O1—C7—C1	118.0 (3)	C27—C26—H26A	120.7
O2—C7—C1	117.8 (3)	N6—C27—C26	122.4 (4)
N3—C8—C9	123.4 (4)	N6—C27—H27A	118.8
N3—C8—H8A	118.3	C26—C27—H27A	118.8
O3—Co1—N3—C8	−100.0 (3)	C2—C1—C6—C5	−2.1 (5)
N5—Co1—N3—C8	−4.6 (3)	C7—C1—C6—C5	176.5 (3)
N4—Co1—N3—C8	173.0 (3)	C4—C5—C6—C1	1.7 (5)
N6—Co1—N3—C8	71.8 (3)	N2—C5—C6—C1	−177.3 (3)
O3—Co1—N3—C12	89.3 (2)	Co1—O2—C7—O1	149.7 (3)
N5—Co1—N3—C12	−175.2 (2)	Co1—O2—C7—C1	−32.9 (4)
N4—Co1—N3—C12	2.4 (2)	C6—C1—C7—O1	35.5 (5)
N6—Co1—N3—C12	−98.9 (2)	C2—C1—C7—O1	−145.9 (4)
O2—Co1—N4—C17	−7.7 (2)	C6—C1—C7—O2	−142.0 (3)
O3—Co1—N4—C17	81.0 (2)	C2—C1—C7—O2	36.6 (5)
N3—Co1—N4—C17	175.4 (3)	C12—N3—C8—C9	1.2 (5)
N6—Co1—N4—C17	−100.2 (2)	Co1—N3—C8—C9	−169.4 (3)
O2—Co1—N4—C13	−179.9 (2)	N3—C8—C9—C10	−1.3 (6)
O3—Co1—N4—C13	−91.2 (2)	C8—C9—C10—C11	0.2 (5)
N3—Co1—N4—C13	3.2 (2)	C9—C10—C11—C12	1.0 (5)
N6—Co1—N4—C13	87.7 (2)	C8—N3—C12—C11	0.1 (4)
O2—Co1—N5—C18	88.5 (3)	Co1—N3—C12—C11	171.4 (2)
O3—Co1—N5—C18	−0.4 (3)	C8—N3—C12—C13	−178.3 (3)
N3—Co1—N5—C18	−94.8 (3)	Co1—N3—C12—C13	−7.0 (3)
N6—Co1—N5—C18	179.7 (3)	C10—C11—C12—N3	−1.1 (5)
O2—Co1—N5—C22	−88.8 (2)	C10—C11—C12—C13	177.1 (3)
O3—Co1—N5—C22	−177.7 (2)	C17—N4—C13—C14	0.4 (4)
N3—Co1—N5—C22	87.9 (2)	Co1—N4—C13—C14	173.0 (2)
N6—Co1—N5—C22	2.4 (2)	C17—N4—C13—C12	179.6 (3)
O2—Co1—N6—C27	−90.8 (3)	Co1—N4—C13—C12	−7.8 (3)
N5—Co1—N6—C27	179.4 (3)	N3—C12—C13—N4	9.8 (4)
N3—Co1—N6—C27	81.9 (3)	C11—C12—C13—N4	−168.6 (3)
N4—Co1—N6—C27	6.5 (3)	N3—C12—C13—C14	−171.1 (3)
O2—Co1—N6—C23	86.5 (2)	C11—C12—C13—C14	10.5 (5)
N5—Co1—N6—C23	−3.3 (2)	N4—C13—C14—C15	0.3 (5)
N3—Co1—N6—C23	−100.8 (2)	C12—C13—C14—C15	−178.8 (3)
N4—Co1—N6—C23	−176.2 (2)	C13—C14—C15—C16	0.2 (6)
O3—Co1—O2—C7	3.1 (3)	C14—C15—C16—C17	−1.2 (7)
N5—Co1—O2—C7	−91.9 (3)	C13—N4—C17—C16	−1.6 (5)
N4—Co1—O2—C7	91.0 (3)	Co1—N4—C17—C16	−173.6 (3)
N6—Co1—O2—C7	−168.6 (3)	C15—C16—C17—N4	2.0 (6)
O2—Co1—O3—C2	32.9 (2)	C22—N5—C18—C19	−0.6 (5)
N5—Co1—O3—C2	122.9 (2)	Co1—N5—C18—C19	−177.9 (3)
N3—Co1—O3—C2	−140.2 (2)	N5—C18—C19—C20	0.2 (6)
N4—Co1—O3—C2	−64.2 (3)	C18—C19—C20—C21	0.1 (6)
Co1—O3—C2—C1	−38.2 (4)	C19—C20—C21—C22	0.0 (6)
Co1—O3—C2—C3	141.4 (2)	C18—N5—C22—C21	0.7 (5)
C6—C1—C2—O3	−179.7 (3)	Co1—N5—C22—C21	178.2 (3)
C7—C1—C2—O3	1.8 (5)	C18—N5—C22—C23	−178.7 (3)
C6—C1—C2—C3	0.7 (4)	Co1—N5—C22—C23	−1.2 (4)
C7—C1—C2—C3	−177.8 (3)	C20—C21—C22—N5	−0.4 (5)
O3—C2—C3—C4	−178.6 (3)	C20—C21—C22—C23	178.9 (3)
C1—C2—C3—C4	1.0 (4)	C27—N6—C23—C24	1.8 (5)
O3—C2—C3—N1	−3.2 (4)	Co1—N6—C23—C24	−175.7 (3)
C1—C2—C3—N1	176.4 (3)	C27—N6—C23—C22	−178.7 (3)
O4—N1—C3—C4	−144.3 (3)	Co1—N6—C23—C22	3.8 (4)
O5—N1—C3—C4	32.0 (4)	N5—C22—C23—N6	−1.8 (4)
O4—N1—C3—C2	39.9 (4)	C21—C22—C23—N6	178.8 (3)
O5—N1—C3—C2	−143.7 (3)	N5—C22—C23—C24	177.7 (3)
C2—C3—C4—C5	−1.3 (5)	C21—C22—C23—C24	−1.7 (5)
N1—C3—C4—C5	−176.9 (3)	N6—C23—C24—C25	−0.7 (6)
C3—C4—C5—C6	0.0 (5)	C22—C23—C24—C25	179.9 (4)
C3—C4—C5—N2	179.0 (3)	C23—C24—C25—C26	−1.2 (6)
O6—N2—C5—C4	−1.7 (5)	C24—C25—C26—C27	1.8 (7)
O7—N2—C5—C4	179.5 (3)	C23—N6—C27—C26	−1.1 (5)
O6—N2—C5—C6	177.4 (3)	Co1—N6—C27—C26	176.1 (3)
O7—N2—C5—C6	−1.4 (5)	C25—C26—C27—N6	−0.7 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O1i	0.93	2.32	3.166 (5)	151
C21—H21A···O1ii	0.93	2.40	3.275 (4)	157
C16—H16A···O4iii	0.93	2.43	3.171 (5)	137
C25—H25A···O6iv	0.93	2.61	3.209 (5)	123
C9—H9A···O5v	0.93	2.61	3.346 (5)	136

Table 1

Selected bond lengths (Å)

Co1—O2	2.036 (2)
Co1—O3	2.047 (2)
Co1—N5	2.116 (2)
Co1—N3	2.132 (3)
Co1—N4	2.133 (3)
Co1—N6	2.141 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O1i	0.93	2.32	3.166 (5)	151
C21—H21A⋯O1ii	0.93	2.40	3.275 (4)	157
C16—H16A⋯O4iii	0.93	2.43	3.171 (5)	137
C25—H25A⋯O6iv	0.93	2.61	3.209 (5)	123
C9—H9A⋯O5v	0.93	2.61	3.346 (5)	136

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