Tetra-kis[μ-4-(diethyl-amino)-benzoato-κO:O']bis-[(N,N-diethyl-nicotinamide-κN)cobalt(II)].

In the centrosymmetric binuclear title complex, [Co(2)(C(11)H(14)NO(2))(4)(C(10)H(14)N(2)O)(2)], the two Co(II) cations [Co⋯Co = 2.6199 (5) Å] are bridged by four 4-(diethyl-amino)-benzoate (DEAB) anions. The four nearest O atoms around each Co(II) ion form a distorted square-planar arrangement, the distorted square-pyramidal coordination geometry being completed by the pyridine N atom of an N,N-diethyl-nicotinamide (DENA) ligand. The dihedral angle between the benzene ring and the carboxyl-ate group is 7.06 (11)° in one of the independent DEAB ligands and 4.42 (9)° in the other. The benzene rings of the two independent DEAB ligands are oriented at a dihedral angle of 86.35 (8)°. The pyridine ring is oriented at dihedral angles of 31.43 (6) and 57.92 (7)° with respect to the two benzene rings. In the crystal, weak inter-molecular C-H⋯O inter-actions link the mol-ecules into a three-dimensional network. Weak C-H⋯π inter-actions are also present in the crystal structure.

Related literature

For niacin, see: Krishnamachari (1974 ▶). For N,N-diethyl­nicotinamide, see: Bigoli et al. (1972 ▶). For related structures, see: Speier & Fulop (1989 ▶); Usubaliev et al. (1980 ▶); Hökelek et al. (1995 ▶, 2009a ▶,b ▶,c ▶); Necefoğlu et al. (2010a ▶,b ▶).

Experimental

Crystal data

[Co2(C11H14NO2)4(C10H14N2O)2]

M = 1243.25

Monoclinic,

a = 10.3518 (2) Å

b = 13.4393 (2) Å

c = 22.5105 (3) Å

β = 94.189 (2)°

V = 3123.32 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.60 mm−1

T = 100 K

0.44 × 0.36 × 0.21 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.771, T max = 0.881

29642 measured reflections

7775 independent reflections

6209 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.119

S = 1.04

7775 reflections

385 parameters

1 restraint

H-atom parameters constrained

Δρmax = 1.86 e Å−3

Δρmin = −0.63 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681005004X/xu5109sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681005004X/xu5109Isup2.hkl

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

[Co2(C11H14NO2)4(C10H14N2O)2]	F(000) = 1316
Mr = 1243.25	Dx = 1.322 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9913 reflections
a = 10.3518 (2) Å	θ = 2.2–28.3°
b = 13.4393 (2) Å	µ = 0.60 mm−1
c = 22.5105 (3) Å	T = 100 K
β = 94.189 (2)°	Block, blue
V = 3123.32 (9) Å3	0.44 × 0.36 × 0.21 mm
Z = 2

Bruker Kappa APEXII CCD area-detector diffractometer	7775 independent reflections
Radiation source: fine-focus sealed tube	6209 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 28.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→11
Tmin = 0.771, Tmax = 0.881	k = −17→15
29642 measured reflections	l = −28→30

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0516P)2 + 3.5237P] where P = (Fo2 + 2Fc2)/3
7775 reflections	(Δ/σ)max < 0.001
385 parameters	Δρmax = 1.86 e Å−3
1 restraint	Δρmin = −0.63 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.08277 (3)	0.50124 (2)	0.046881 (12)	0.01343 (9)
O1	0.21346 (15)	0.45553 (12)	−0.01024 (7)	0.0193 (3)
O2	−0.07212 (15)	0.54348 (12)	0.09087 (7)	0.0213 (3)
O3	0.02198 (15)	0.35760 (11)	0.05110 (7)	0.0204 (3)
O4	0.12056 (16)	0.64540 (11)	0.02910 (7)	0.0207 (3)
O5	0.39349 (16)	0.22715 (12)	0.22409 (8)	0.0272 (4)
N1	0.19986 (17)	0.48455 (13)	0.12480 (8)	0.0155 (4)
N2	0.54359 (17)	0.28424 (13)	0.16426 (9)	0.0184 (4)
N3	0.57041 (18)	0.27458 (14)	−0.20266 (8)	0.0192 (4)
N4	−0.1917 (3)	−0.08369 (19)	0.07254 (13)	0.0586 (9)
C1	0.1838 (2)	0.44190 (15)	−0.06537 (10)	0.0164 (4)
C2	0.2870 (2)	0.40483 (15)	−0.10227 (10)	0.0161 (4)
C3	0.4103 (2)	0.38332 (16)	−0.07660 (10)	0.0174 (4)
H3	0.4295	0.3974	−0.0365	0.021*
C4	0.5050 (2)	0.34162 (16)	−0.10906 (10)	0.0181 (4)
H4	0.5861	0.3275	−0.0904	0.022*
C5	0.4795 (2)	0.32034 (16)	−0.17039 (10)	0.0169 (4)
C6	0.3572 (2)	0.34872 (17)	−0.19684 (10)	0.0201 (4)
H6	0.3395	0.3403	−0.2376	0.024*
C7	0.2632 (2)	0.38885 (16)	−0.16323 (10)	0.0188 (4)
H7	0.1828	0.4054	−0.1817	0.023*
C8	0.5472 (2)	0.25945 (19)	−0.26694 (10)	0.0238 (5)
H8A	0.6303	0.2546	−0.2840	0.029*
H8B	0.5035	0.3179	−0.2839	0.029*
C9	0.4673 (3)	0.1681 (2)	−0.28582 (12)	0.0304 (6)
H9A	0.4543	0.1663	−0.3285	0.046*
H9B	0.3849	0.1713	−0.2689	0.046*
H9C	0.5124	0.1092	−0.2720	0.046*
C10	0.6810 (2)	0.22247 (17)	−0.17283 (10)	0.0202 (4)
H10A	0.7188	0.2642	−0.1409	0.024*
H10B	0.7461	0.2124	−0.2011	0.024*
C11	0.6460 (3)	0.12205 (18)	−0.14698 (11)	0.0273 (5)
H11A	0.7227	0.0911	−0.1289	0.041*
H11B	0.6087	0.0802	−0.1782	0.041*
H11C	0.5846	0.1316	−0.1175	0.041*
C12	−0.0614 (2)	0.31422 (16)	0.01624 (10)	0.0173 (4)
C13	−0.0922 (2)	0.20945 (16)	0.02986 (10)	0.0187 (4)
C14	−0.1889 (2)	0.15828 (17)	−0.00377 (11)	0.0241 (5)
H14	−0.2324	0.1899	−0.0361	0.029*
C15	−0.2217 (3)	0.06189 (18)	0.00965 (12)	0.0313 (6)
H15	−0.2872	0.0299	−0.0135	0.038*
C16	−0.1573 (3)	0.01105 (19)	0.05801 (13)	0.0363 (7)
C17	−0.0571 (3)	0.06262 (18)	0.09112 (12)	0.0322 (6)
H17	−0.0107	0.0308	0.1225	0.039*
C18	−0.0274 (2)	0.15955 (17)	0.07739 (11)	0.0237 (5)
H18	0.0374	0.1924	0.1004	0.028*
C19	−0.3105 (3)	−0.1314 (2)	0.04357 (14)	0.0422 (7)
H19A	−0.3446	−0.1795	0.0705	0.051*
H19B	−0.3764	−0.0813	0.0344	0.051*
C20	−0.2775 (3)	−0.1820 (2)	−0.01213 (16)	0.0477 (8)
H20A	−0.3547	−0.2089	−0.0322	0.072*
H20B	−0.2171	−0.2348	−0.0025	0.072*
H20C	−0.2393	−0.1348	−0.0377	0.072*
C21	−0.1063 (5)	−0.1455 (3)	0.11570 (18)	0.0771 (14)
H21A	−0.1127	−0.2154	0.1052	0.093*
H21B	−0.0165	−0.1250	0.1149	0.093*
C22	−0.1526 (4)	−0.1287 (3)	0.1752 (2)	0.0805 (13)
H22A	−0.1052	−0.1704	0.2037	0.121*
H22B	−0.2432	−0.1445	0.1745	0.121*
H22C	−0.1398	−0.0602	0.1863	0.121*
C23	0.1870 (2)	0.54421 (16)	0.17171 (10)	0.0172 (4)
H23	0.1288	0.5969	0.1677	0.021*
C24	0.2571 (2)	0.53051 (17)	0.22588 (10)	0.0202 (4)
H24	0.2475	0.5741	0.2573	0.024*
C25	0.3415 (2)	0.45098 (17)	0.23237 (10)	0.0196 (4)
H25	0.3887	0.4398	0.2685	0.024*
C26	0.3553 (2)	0.38771 (16)	0.18422 (10)	0.0169 (4)
C27	0.2831 (2)	0.40772 (16)	0.13115 (10)	0.0165 (4)
H27	0.2927	0.3663	0.0986	0.020*
C28	0.4338 (2)	0.29336 (16)	0.19214 (10)	0.0181 (4)
C29	0.6145 (2)	0.18977 (17)	0.17123 (11)	0.0241 (5)
H29A	0.6180	0.1699	0.2127	0.029*
H29B	0.7027	0.2000	0.1607	0.029*
C30	0.5542 (3)	0.10637 (19)	0.13335 (14)	0.0355 (6)
H30A	0.6006	0.0457	0.1422	0.053*
H30B	0.5585	0.1224	0.0920	0.053*
H30C	0.4653	0.0982	0.1419	0.053*
C31	0.6028 (2)	0.36507 (17)	0.13149 (10)	0.0209 (5)
H31A	0.6913	0.3750	0.1478	0.025*
H31B	0.5555	0.4262	0.1370	0.025*
C32	0.6032 (3)	0.3432 (2)	0.06586 (12)	0.0313 (6)
H32A	0.6430	0.3975	0.0463	0.047*
H32B	0.5157	0.3351	0.0493	0.047*
H32C	0.6510	0.2833	0.0601	0.047*

	U11	U22	U33	U12	U13	U23
Co1	0.01556 (14)	0.01128 (15)	0.01370 (14)	−0.00036 (11)	0.00279 (10)	0.00104 (10)
O1	0.0209 (7)	0.0199 (8)	0.0177 (8)	0.0017 (6)	0.0049 (6)	−0.0005 (6)
O2	0.0182 (7)	0.0254 (8)	0.0207 (8)	0.0029 (7)	0.0043 (6)	−0.0011 (7)
O3	0.0260 (8)	0.0135 (7)	0.0216 (8)	−0.0054 (6)	0.0012 (6)	0.0013 (6)
O4	0.0275 (8)	0.0131 (7)	0.0215 (8)	−0.0015 (6)	0.0008 (6)	0.0037 (6)
O5	0.0278 (9)	0.0215 (9)	0.0339 (10)	0.0041 (7)	0.0120 (7)	0.0105 (7)
N1	0.0158 (8)	0.0128 (8)	0.0185 (9)	−0.0021 (7)	0.0050 (7)	0.0009 (7)
N2	0.0171 (8)	0.0159 (9)	0.0222 (10)	0.0012 (7)	0.0022 (7)	0.0042 (7)
N3	0.0192 (9)	0.0223 (10)	0.0167 (9)	0.0029 (7)	0.0047 (7)	−0.0013 (7)
N4	0.086 (2)	0.0262 (12)	0.0576 (17)	−0.0294 (13)	−0.0359 (15)	0.0207 (12)
C1	0.0200 (10)	0.0109 (9)	0.0190 (10)	−0.0019 (8)	0.0060 (8)	0.0006 (8)
C2	0.0174 (9)	0.0129 (9)	0.0185 (10)	−0.0012 (8)	0.0050 (8)	0.0010 (8)
C3	0.0215 (10)	0.0147 (10)	0.0161 (10)	−0.0001 (8)	0.0025 (8)	0.0008 (8)
C4	0.0172 (10)	0.0180 (10)	0.0193 (10)	0.0011 (8)	0.0020 (8)	0.0000 (8)
C5	0.0174 (10)	0.0156 (10)	0.0185 (10)	−0.0019 (8)	0.0059 (8)	−0.0005 (8)
C6	0.0217 (10)	0.0231 (11)	0.0157 (10)	0.0007 (9)	0.0025 (8)	−0.0026 (8)
C7	0.0165 (10)	0.0195 (11)	0.0204 (11)	0.0008 (8)	0.0017 (8)	−0.0004 (8)
C8	0.0231 (11)	0.0319 (13)	0.0171 (11)	0.0038 (10)	0.0069 (9)	−0.0034 (9)
C9	0.0311 (13)	0.0335 (14)	0.0265 (13)	0.0028 (11)	0.0015 (10)	−0.0082 (11)
C10	0.0183 (10)	0.0204 (11)	0.0226 (11)	0.0016 (9)	0.0068 (8)	−0.0017 (9)
C11	0.0363 (13)	0.0214 (12)	0.0240 (12)	−0.0005 (10)	0.0022 (10)	−0.0002 (9)
C12	0.0200 (10)	0.0134 (10)	0.0190 (10)	−0.0004 (8)	0.0064 (8)	−0.0002 (8)
C13	0.0246 (11)	0.0134 (10)	0.0184 (11)	−0.0022 (8)	0.0026 (8)	0.0006 (8)
C14	0.0320 (12)	0.0181 (11)	0.0212 (11)	−0.0049 (9)	−0.0042 (9)	0.0041 (9)
C15	0.0408 (14)	0.0199 (12)	0.0311 (14)	−0.0116 (11)	−0.0117 (11)	0.0042 (10)
C16	0.0547 (17)	0.0178 (12)	0.0341 (15)	−0.0142 (12)	−0.0137 (13)	0.0082 (10)
C17	0.0472 (15)	0.0181 (12)	0.0289 (13)	−0.0091 (11)	−0.0138 (12)	0.0103 (10)
C18	0.0306 (12)	0.0166 (11)	0.0230 (12)	−0.0071 (9)	−0.0037 (9)	0.0028 (9)
C19	0.0583 (18)	0.0207 (13)	0.0479 (17)	−0.0097 (13)	0.0050 (14)	0.0037 (12)
C20	0.0459 (17)	0.0360 (16)	0.062 (2)	0.0028 (14)	0.0069 (15)	0.0019 (14)
C21	0.113 (3)	0.047 (2)	0.065 (2)	−0.049 (2)	−0.030 (2)	0.0196 (17)
C22	0.070 (2)	0.070 (3)	0.099 (3)	−0.024 (2)	−0.007 (2)	0.019 (2)
C23	0.0184 (10)	0.0137 (10)	0.0200 (11)	−0.0011 (8)	0.0040 (8)	−0.0006 (8)
C24	0.0240 (11)	0.0171 (10)	0.0197 (11)	−0.0024 (9)	0.0030 (9)	−0.0039 (8)
C25	0.0207 (10)	0.0200 (11)	0.0180 (10)	−0.0018 (9)	0.0001 (8)	0.0019 (9)
C26	0.0164 (9)	0.0152 (10)	0.0194 (11)	−0.0009 (8)	0.0036 (8)	0.0030 (8)
C27	0.0175 (10)	0.0145 (10)	0.0178 (10)	−0.0002 (8)	0.0045 (8)	−0.0004 (8)
C28	0.0188 (10)	0.0165 (10)	0.0191 (11)	0.0012 (8)	0.0013 (8)	0.0018 (8)
C29	0.0205 (11)	0.0220 (12)	0.0302 (13)	0.0057 (9)	0.0039 (9)	0.0080 (10)
C30	0.0405 (15)	0.0180 (12)	0.0485 (17)	0.0036 (11)	0.0076 (13)	−0.0009 (11)
C31	0.0177 (10)	0.0175 (11)	0.0278 (12)	−0.0018 (8)	0.0037 (9)	0.0037 (9)
C32	0.0389 (14)	0.0290 (13)	0.0269 (13)	−0.0101 (11)	0.0086 (11)	0.0037 (10)

Co1—Co1i	2.6199 (5)	C12—C13	1.481 (3)
Co1—O1	2.0287 (15)	C13—C14	1.392 (3)
Co1—O2	2.0262 (16)	C14—C15	1.378 (3)
Co1—O3	2.0347 (15)	C14—H14	0.9300
Co1—O4	2.0223 (15)	C15—C16	1.411 (4)
Co1—N1	2.0702 (18)	C15—H15	0.9300
O1—C1	1.270 (3)	C17—C16	1.414 (4)
O2—C1i	1.268 (3)	C17—H17	0.9300
O3—C12	1.266 (3)	C18—C13	1.393 (3)
O4—C12i	1.273 (3)	C18—C17	1.379 (3)
O5—C28	1.236 (3)	C18—H18	0.9300
N1—C23	1.340 (3)	C19—C20	1.488 (4)
N1—C27	1.346 (3)	C19—H19A	0.9700
N2—C28	1.343 (3)	C19—H19B	0.9700
N2—C29	1.469 (3)	C20—H20A	0.9600
N2—C31	1.472 (3)	C20—H20B	0.9600
N3—C8	1.464 (3)	C20—H20C	0.9600
N4—C16	1.368 (3)	C21—N4	1.513 (4)
N4—C19	1.494 (4)	C21—C22	1.474 (6)
C1—O2i	1.268 (3)	C21—H21A	0.9700
C1—C2	1.486 (3)	C21—H21B	0.9700
C2—C7	1.393 (3)	C22—H22A	0.9600
C3—C2	1.392 (3)	C22—H22B	0.9600
C3—C4	1.384 (3)	C22—H22C	0.9600
C3—H3	0.9300	C23—C24	1.385 (3)
C4—C5	1.416 (3)	C23—H23	0.9300
C4—H4	0.9300	C24—C25	1.381 (3)
C5—N3	1.375 (3)	C24—H24	0.9300
C5—C6	1.412 (3)	C25—H25	0.9300
C6—C7	1.385 (3)	C26—C25	1.393 (3)
C6—H6	0.9300	C26—C28	1.510 (3)
C7—H7	0.9300	C27—C26	1.388 (3)
C8—C9	1.523 (3)	C27—H27	0.9300
C8—H8A	0.9700	C29—C30	1.515 (4)
C8—H8B	0.9700	C29—H29A	0.9700
C9—H9A	0.9600	C29—H29B	0.9700
C9—H9B	0.9600	C30—H30A	0.9600
C9—H9C	0.9600	C30—H30B	0.9600
C10—N3	1.462 (3)	C30—H30C	0.9600
C10—C11	1.524 (3)	C31—C32	1.506 (3)
C10—H10A	0.9700	C31—H31A	0.9700
C10—H10B	0.9700	C31—H31B	0.9700
C11—H11A	0.9600	C32—H32A	0.9600
C11—H11B	0.9600	C32—H32B	0.9600
C11—H11C	0.9600	C32—H32C	0.9600
C12—O4i	1.273 (3)
O1—Co1—Co1i	84.99 (5)	C15—C14—C13	121.6 (2)
O1—Co1—O3	88.00 (7)	C15—C14—H14	119.2
O1—Co1—N1	97.35 (7)	C13—C14—H14	119.2
O2—Co1—Co1i	84.43 (5)	C14—C15—C16	120.9 (2)
O2—Co1—O1	169.35 (6)	C14—C15—H15	119.5
O2—Co1—O3	89.11 (7)	C16—C15—H15	119.5
O2—Co1—N1	92.95 (7)	N4—C16—C15	121.2 (2)
O3—Co1—Co1i	80.75 (5)	N4—C16—C17	121.6 (2)
O3—Co1—N1	91.24 (6)	C15—C16—C17	117.2 (2)
O4—Co1—Co1i	88.70 (5)	C16—C17—H17	119.6
O4—Co1—O1	90.98 (7)	C18—C17—C16	120.8 (2)
O4—Co1—O2	89.99 (7)	C18—C17—H17	119.6
O4—Co1—O3	169.45 (6)	C13—C18—H18	119.2
O4—Co1—N1	99.31 (7)	C17—C18—C13	121.6 (2)
N1—Co1—Co1i	171.59 (5)	C17—C18—H18	119.2
C1—O1—Co1	122.57 (14)	N4—C19—H19A	109.8
C1i—O2—Co1	123.37 (14)	N4—C19—H19B	109.8
C12—O3—Co1	127.39 (14)	C20—C19—N4	109.3 (3)
C12i—O4—Co1	118.59 (14)	C20—C19—H19A	109.8
C23—N1—C27	118.36 (19)	C20—C19—H19B	109.8
C23—N1—Co1	121.14 (14)	H19A—C19—H19B	108.3
C27—N1—Co1	120.25 (15)	C19—C20—H20A	109.5
C28—N2—C29	117.52 (18)	C19—C20—H20B	109.5
C28—N2—C31	124.37 (18)	C19—C20—H20C	109.5
C29—N2—C31	117.91 (18)	H20A—C20—H20B	109.5
C5—N3—C10	120.94 (18)	H20A—C20—H20C	109.5
C5—N3—C8	121.00 (18)	H20B—C20—H20C	109.5
C10—N3—C8	117.01 (18)	N4—C21—H21A	110.4
C16—N4—C19	121.0 (2)	N4—C21—H21B	110.4
C16—N4—C21	120.9 (3)	C22—C21—N4	106.6 (4)
C19—N4—C21	117.9 (2)	C22—C21—H21A	110.4
O1—C1—C2	117.53 (19)	C22—C21—H21B	110.4
O2i—C1—O1	124.6 (2)	H21A—C21—H21B	108.6
O2i—C1—C2	117.88 (19)	C21—C22—H22A	109.5
C3—C2—C1	120.80 (19)	C21—C22—H22B	109.5
C3—C2—C7	117.9 (2)	C21—C22—H22C	109.5
C7—C2—C1	121.32 (19)	H22A—C22—H22B	109.5
C2—C3—H3	119.0	H22A—C22—H22C	109.5
C4—C3—C2	121.9 (2)	H22B—C22—H22C	109.5
C4—C3—H3	119.0	N1—C23—C24	122.6 (2)
C3—C4—C5	120.5 (2)	N1—C23—H23	118.7
C3—C4—H4	119.7	C24—C23—H23	118.7
C5—C4—H4	119.7	C23—C24—H24	120.6
N3—C5—C4	121.31 (19)	C25—C24—C23	118.9 (2)
N3—C5—C6	121.7 (2)	C25—C24—H24	120.6
C6—C5—C4	117.01 (19)	C24—C25—C26	119.3 (2)
C5—C6—H6	119.4	C24—C25—H25	120.3
C7—C6—C5	121.3 (2)	C26—C25—H25	120.3
C7—C6—H6	119.4	C25—C26—C28	120.36 (19)
C2—C7—H7	119.4	C27—C26—C25	118.2 (2)
C6—C7—C2	121.2 (2)	C27—C26—C28	121.0 (2)
C6—C7—H7	119.4	N1—C27—C26	122.7 (2)
N3—C8—C9	115.8 (2)	N1—C27—H27	118.7
N3—C8—H8A	108.3	C26—C27—H27	118.7
N3—C8—H8B	108.3	O5—C28—N2	122.6 (2)
C9—C8—H8A	108.3	O5—C28—C26	118.14 (19)
C9—C8—H8B	108.3	N2—C28—C26	119.22 (19)
H8A—C8—H8B	107.4	N2—C29—C30	113.4 (2)
C8—C9—H9A	109.5	N2—C29—H29A	108.9
C8—C9—H9B	109.5	N2—C29—H29B	108.9
C8—C9—H9C	109.5	C30—C29—H29A	108.9
H9A—C9—H9B	109.5	C30—C29—H29B	108.9
H9A—C9—H9C	109.5	H29A—C29—H29B	107.7
H9B—C9—H9C	109.5	C29—C30—H30A	109.5
N3—C10—C11	113.57 (19)	C29—C30—H30B	109.5
N3—C10—H10A	108.9	C29—C30—H30C	109.5
N3—C10—H10B	108.9	H30A—C30—H30B	109.5
C11—C10—H10A	108.9	H30A—C30—H30C	109.5
C11—C10—H10B	108.9	H30B—C30—H30C	109.5
H10A—C10—H10B	107.7	N2—C31—C32	112.25 (19)
C10—C11—H11A	109.5	N2—C31—H31A	109.2
C10—C11—H11B	109.5	N2—C31—H31B	109.2
C10—C11—H11C	109.5	C32—C31—H31A	109.2
H11A—C11—H11B	109.5	C32—C31—H31B	109.2
H11A—C11—H11C	109.5	H31A—C31—H31B	107.9
H11B—C11—H11C	109.5	C31—C32—H32A	109.5
O3—C12—O4i	124.6 (2)	C31—C32—H32B	109.5
O3—C12—C13	117.19 (19)	C31—C32—H32C	109.5
O4i—C12—C13	118.26 (19)	H32A—C32—H32B	109.5
C14—C13—C12	121.0 (2)	H32A—C32—H32C	109.5
C14—C13—C18	117.8 (2)	H32B—C32—H32C	109.5
C18—C13—C12	121.2 (2)
Co1i—Co1—O1—C1	0.51 (16)	C21—N4—C16—C17	−13.4 (6)
O2—Co1—O1—C1	7.0 (4)	C16—N4—C19—C20	88.1 (4)
O3—Co1—O1—C1	81.40 (16)	C21—N4—C19—C20	−88.3 (4)
O4—Co1—O1—C1	−88.10 (16)	O1—C1—C2—C3	1.8 (3)
N1—Co1—O1—C1	172.39 (16)	O1—C1—C2—C7	−179.3 (2)
Co1i—Co1—O2—C1i	−2.46 (16)	O2i—C1—C2—C3	−177.3 (2)
O1—Co1—O2—C1i	−9.0 (5)	O2i—C1—C2—C7	1.5 (3)
O3—Co1—O2—C1i	−83.25 (17)	C1—C2—C7—C6	−176.1 (2)
O4—Co1—O2—C1i	86.23 (17)	C3—C2—C7—C6	2.8 (3)
N1—Co1—O2—C1i	−174.45 (17)	C4—C3—C2—C1	175.0 (2)
Co1i—Co1—O3—C12	−0.78 (17)	C4—C3—C2—C7	−3.9 (3)
O1—Co1—O3—C12	−86.04 (18)	C2—C3—C4—C5	0.7 (3)
O2—Co1—O3—C12	83.71 (18)	C3—C4—C5—N3	−176.9 (2)
O4—Co1—O3—C12	−1.4 (5)	C3—C4—C5—C6	3.5 (3)
N1—Co1—O3—C12	176.65 (18)	C4—C5—N3—C8	−175.4 (2)
Co1i—Co1—O4—C12i	−0.42 (16)	C4—C5—N3—C10	16.7 (3)
O1—Co1—O4—C12i	84.55 (16)	C6—C5—N3—C8	4.2 (3)
O2—Co1—O4—C12i	−84.85 (16)	C6—C5—N3—C10	−163.7 (2)
O3—Co1—O4—C12i	0.2 (5)	N3—C5—C6—C7	175.8 (2)
N1—Co1—O4—C12i	−177.84 (16)	C4—C5—C6—C7	−4.6 (3)
O1—Co1—N1—C23	148.47 (16)	C5—C6—C7—C2	1.5 (3)
O1—Co1—N1—C27	−37.35 (16)	C11—C10—N3—C5	75.1 (3)
O2—Co1—N1—C23	−34.21 (17)	C11—C10—N3—C8	−93.3 (2)
O2—Co1—N1—C27	139.96 (16)	O3—C12—C13—C14	175.7 (2)
O3—Co1—N1—C23	−123.39 (16)	O3—C12—C13—C18	−3.0 (3)
O3—Co1—N1—C27	50.79 (16)	O4i—C12—C13—C14	−3.9 (3)
O4—Co1—N1—C23	56.26 (17)	O4i—C12—C13—C18	177.4 (2)
O4—Co1—N1—C27	−129.56 (16)	C12—C13—C14—C15	−177.7 (2)
Co1—O1—C1—O2i	1.2 (3)	C18—C13—C14—C15	1.0 (4)
Co1—O1—C1—C2	−177.85 (13)	C13—C14—C15—C16	−0.5 (4)
Co1—O3—C12—O4i	1.4 (3)	C14—C15—C16—N4	178.3 (3)
Co1—O3—C12—C13	−178.13 (14)	C14—C15—C16—C17	−1.0 (5)
Co1—N1—C23—C24	175.15 (16)	C18—C17—C16—N4	−177.2 (3)
C27—N1—C23—C24	0.9 (3)	C18—C17—C16—C15	2.0 (5)
Co1—N1—C27—C26	−174.00 (16)	C17—C18—C13—C14	0.0 (4)
C23—N1—C27—C26	0.3 (3)	C17—C18—C13—C12	178.7 (2)
C29—N2—C28—O5	2.0 (3)	C13—C18—C17—C16	−1.6 (4)
C29—N2—C28—C26	−177.65 (19)	C22—C21—N4—C16	92.5 (4)
C31—N2—C28—O5	−172.7 (2)	C22—C21—N4—C19	−91.1 (4)
C31—N2—C28—C26	7.6 (3)	N1—C23—C24—C25	−1.5 (3)
C28—N2—C29—C30	77.2 (3)	C23—C24—C25—C26	0.9 (3)
C31—N2—C29—C30	−107.8 (2)	C27—C26—C25—C24	0.2 (3)
C28—N2—C31—C32	−115.2 (2)	C28—C26—C25—C24	−172.4 (2)
C29—N2—C31—C32	70.2 (3)	C25—C26—C28—O5	66.0 (3)
C5—N3—C8—C9	−83.0 (3)	C25—C26—C28—N2	−114.4 (2)
C10—N3—C8—C9	85.4 (2)	C27—C26—C28—O5	−106.4 (3)
C19—N4—C16—C15	−8.9 (5)	C27—C26—C28—N2	73.2 (3)
C19—N4—C16—C17	170.2 (3)	N1—C27—C26—C25	−0.9 (3)
C21—N4—C16—C15	167.4 (4)	N1—C27—C26—C28	171.70 (19)

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O5ii	0.97	2.49	3.380 (3)	153
C24—H24···O5iii	0.93	2.57	3.307 (3)	136
C19—H19A···Cg1iv	0.97	2.94	3.872 (3)	162
C31—H31B···Cg1v	0.97	2.88	3.637 (2)	136

Table 1

Selected bond lengths (Å)

Co1—O1	2.0287 (15)
Co1—O2	2.0262 (16)
Co1—O3	2.0347 (15)
Co1—O4	2.0223 (15)
Co1—N1	2.0702 (18)

Table 2

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O5i	0.97	2.49	3.380 (3)	153
C24—H24⋯O5ii	0.93	2.57	3.307 (3)	136
C19—H19A⋯Cg1iii	0.97	2.94	3.872 (3)	162
C31—H31B⋯Cg1iv	0.97	2.88	3.637 (2)	136

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