Diaqua-bis(4-methyl-amino-benzoato-κO)bis-(nicotinamide-κN)cobalt(II).

The asymmetric unit of the title Co(II) complex, [Co(C(8)H(8)NO(2))(2)(C(6)H(6)N(2)O)(2)(H(2)O)(2)], contains two half complex mol-ecules with similar structures. The Co(II) atoms are each located on an inversion center and each is coordinated by two 4-methyl-amino-benzoate (PMAB), two nicotinamide (NA) ligands and two water mol-ecules in a distorted octa-hedral coordination. The dihedral angles between the carboxyl-ate groups and the adjacent benzene rings are 3.0 (3) and 2.54 (19)°, while the pyridine and benzene rings are oriented at dihedral angles of 67.40 (8) and 66.25 (8)°. In the crystal structure, inter-molecular O-H⋯O and N-H⋯O hydrogen bonds link the mol-ecules into a supra-molecular structure.

Related literature

For niacin, see: Krishnamachari (1974 ▶) and for the nicotinic acid derivative N,N-diethyl­nicotinamide, see: Bigoli et al. (1972 ▶). For related structures, see: Hökelek et al. (1996 ▶); Hökelek & Necefoğlu (1998 ▶); Hökelek et al. (2009a ▶,b ▶,c ▶).

Experimental

Crystal data

[Co(C8H8NO2)2(C6H6N2O)2(H2O)2]

M = 639.53

Triclinic,

a = 9.9014 (7) Å

b = 11.2891 (8) Å

c = 14.1824 (9) Å

α = 107.554 (5)°

β = 92.975 (4)°

γ = 92.836 (4)°

V = 1505.89 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.63 mm−1

T = 294 K

0.31 × 0.14 × 0.11 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.889, T max = 0.934

25128 measured reflections

7337 independent reflections

3927 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.120

S = 0.99

7337 reflections

433 parameters

11 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.64 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: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810010706/xu2735sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010706/xu2735Isup2.hkl

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

[Co(C8H8NO2)2(C6H6N2O)2(H2O)2]	Z = 2
Mr = 639.53	F(000) = 666
Triclinic, P1	Dx = 1.410 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9014 (7) Å	Cell parameters from 4808 reflections
b = 11.2891 (8) Å	θ = 2.5–22.9°
c = 14.1824 (9) Å	µ = 0.63 mm−1
α = 107.554 (5)°	T = 294 K
β = 92.975 (4)°	Block, orange
γ = 92.836 (4)°	0.31 × 0.14 × 0.11 mm
V = 1505.89 (18) Å3

Bruker Kappa APEXII CCD area-detector diffractometer	7337 independent reflections
Radiation source: fine-focus sealed tube	3927 reflections with I > 2σ(I)
graphite	Rint = 0.050
φ and ω scans	θmax = 28.3°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→13
Tmin = 0.889, Tmax = 0.934	k = −14→15
25128 measured reflections	l = −18→18

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.0507P)2] where P = (Fo2 + 2Fc2)/3
7337 reflections	(Δ/σ)max < 0.001
433 parameters	Δρmax = 0.44 e Å−3
11 restraints	Δρmin = −0.64 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 > 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	0.5000	0.5000	0.5000	0.03935 (17)
Co2	1.0000	1.0000	0.0000	0.03728 (17)
O1	0.56594 (18)	0.56020 (18)	0.38612 (14)	0.0449 (5)
O2	0.71996 (19)	0.7140 (2)	0.46562 (16)	0.0532 (6)
O3	0.8902 (2)	0.2578 (2)	0.27847 (16)	0.0663 (7)
O4	0.4510 (3)	0.3195 (2)	0.40609 (19)	0.0673 (7)
H41	0.447 (4)	0.285 (3)	0.3417 (13)	0.095 (14)*
H42	0.383 (3)	0.283 (4)	0.428 (3)	0.135 (18)*
O5	1.07631 (18)	0.95050 (19)	0.12042 (14)	0.0472 (5)
O6	1.1978 (2)	0.7922 (2)	0.04475 (15)	0.0528 (6)
O7	0.5387 (3)	0.7866 (4)	−0.21529 (18)	0.1282 (14)
O8	0.98305 (19)	1.1857 (2)	0.09213 (16)	0.0472 (5)
H81	0.958 (3)	1.207 (3)	0.1553 (12)	0.083 (12)*
H82	0.918 (3)	1.215 (3)	0.056 (2)	0.104 (15)*
N1	0.8652 (4)	0.6271 (3)	0.0185 (3)	0.0932 (13)
H1	0.931 (4)	0.680 (4)	0.027 (3)	0.101 (16)*
N2	0.7005 (2)	0.4443 (2)	0.52402 (18)	0.0444 (6)
N3	1.0849 (3)	0.2554 (3)	0.3640 (2)	0.0585 (8)
H31	1.122 (3)	0.222 (3)	0.3086 (17)	0.072 (12)*
H32	1.135 (3)	0.264 (3)	0.4217 (18)	0.075 (12)*
N4	1.3862 (4)	0.8673 (3)	0.4966 (2)	0.0738 (9)
H4A	1.441 (4)	0.808 (3)	0.495 (3)	0.125 (19)*
N5	0.7987 (2)	0.9412 (2)	0.02697 (17)	0.0395 (6)
N6	0.3613 (3)	0.7723 (3)	−0.1287 (2)	0.0589 (8)
H61	0.322 (3)	0.782 (4)	−0.0709 (19)	0.097 (15)*
H62	0.313 (3)	0.739 (3)	−0.1852 (18)	0.094 (14)*
C1	0.6647 (3)	0.6378 (3)	0.3879 (2)	0.0394 (7)
C2	0.7153 (3)	0.6358 (3)	0.2905 (2)	0.0407 (7)
C3	0.8201 (3)	0.7192 (3)	0.2835 (2)	0.0469 (8)
H3	0.8571	0.7793	0.3407	0.056*
C4	0.8694 (3)	0.7144 (3)	0.1946 (3)	0.0557 (9)
H4	0.9404	0.7704	0.1925	0.067*
C5	0.8157 (4)	0.6279 (3)	0.1075 (3)	0.0608 (9)
C6	0.7106 (4)	0.5444 (3)	0.1136 (2)	0.0702 (11)
H6	0.6731	0.4847	0.0564	0.084*
C7	0.6619 (3)	0.5501 (3)	0.2042 (2)	0.0581 (9)
H7	0.5910	0.4943	0.2068	0.070*
C8	0.8172 (6)	0.5427 (5)	−0.0756 (3)	0.130 (2)
H8A	0.8674	0.5600	−0.1266	0.194*
H8B	0.7227	0.5524	−0.0880	0.194*
H8C	0.8290	0.4588	−0.0756	0.194*
C9	0.7586 (3)	0.4567 (3)	0.6138 (2)	0.0510 (8)
H9	0.7126	0.4949	0.6694	0.061*
C10	0.8847 (3)	0.4149 (3)	0.6270 (2)	0.0586 (9)
H10	0.9228	0.4254	0.6905	0.070*
C11	0.9534 (3)	0.3580 (3)	0.5463 (2)	0.0504 (8)
H11	1.0387	0.3300	0.5544	0.060*
C12	0.8947 (3)	0.3427 (3)	0.4525 (2)	0.0372 (7)
C13	0.7679 (3)	0.3875 (3)	0.4461 (2)	0.0427 (7)
H13	0.7273	0.3771	0.3833	0.051*
C14	0.9565 (3)	0.2822 (3)	0.3585 (2)	0.0434 (7)
C15	1.1621 (3)	0.8704 (3)	0.1220 (2)	0.0412 (7)
C16	1.2203 (3)	0.8699 (3)	0.2201 (2)	0.0392 (7)
C17	1.3176 (3)	0.7886 (3)	0.2286 (2)	0.0444 (7)
H17	1.3464	0.7329	0.1716	0.053*
C18	1.3718 (3)	0.7889 (3)	0.3193 (2)	0.0506 (8)
H18	1.4372	0.7338	0.3227	0.061*
C19	1.3313 (3)	0.8698 (3)	0.4065 (2)	0.0512 (8)
C20	1.2335 (3)	0.9511 (3)	0.3987 (2)	0.0610 (9)
H20	1.2043	1.0065	0.4556	0.073*
C21	1.1798 (3)	0.9499 (3)	0.3069 (2)	0.0542 (8)
H21	1.1141	1.0046	0.3033	0.065*
C22	1.3480 (4)	0.9441 (4)	0.5901 (3)	0.0900 (13)
H22A	1.3968	0.9234	0.6426	0.135*
H22B	1.2524	0.9305	0.5946	0.135*
H22C	1.3693	1.0300	0.5959	0.135*
C23	0.7582 (3)	0.9468 (3)	0.1165 (2)	0.0473 (8)
H23	0.8186	0.9812	0.1716	0.057*
C24	0.6309 (3)	0.9038 (3)	0.1305 (2)	0.0555 (9)
H24	0.6069	0.9080	0.1939	0.067*
C25	0.5397 (3)	0.8547 (3)	0.0506 (2)	0.0500 (8)
H25	0.4525	0.8269	0.0590	0.060*
C26	0.5796 (3)	0.8473 (3)	−0.0430 (2)	0.0413 (7)
C27	0.7095 (3)	0.8909 (3)	−0.0501 (2)	0.0423 (7)
H27	0.7370	0.8850	−0.1130	0.051*
C28	0.4910 (3)	0.7982 (3)	−0.1358 (2)	0.0597 (9)

	U11	U22	U33	U12	U13	U23
Co1	0.0366 (3)	0.0502 (4)	0.0358 (3)	0.0086 (3)	0.0118 (2)	0.0174 (3)
Co2	0.0287 (3)	0.0528 (4)	0.0361 (3)	0.0039 (2)	0.0022 (2)	0.0220 (3)
O1	0.0377 (11)	0.0619 (13)	0.0409 (12)	−0.0003 (10)	0.0061 (9)	0.0244 (11)
O2	0.0475 (13)	0.0688 (15)	0.0435 (13)	−0.0024 (11)	0.0024 (10)	0.0185 (12)
O3	0.0491 (13)	0.1049 (19)	0.0384 (13)	0.0182 (13)	−0.0002 (11)	0.0104 (13)
O4	0.0795 (18)	0.0634 (16)	0.0509 (17)	−0.0046 (13)	0.0278 (14)	0.0030 (14)
O5	0.0372 (11)	0.0688 (14)	0.0457 (13)	0.0121 (10)	0.0036 (9)	0.0312 (11)
O6	0.0536 (13)	0.0680 (15)	0.0419 (13)	0.0137 (11)	0.0028 (11)	0.0229 (12)
O7	0.091 (2)	0.226 (4)	0.0340 (15)	−0.069 (2)	0.0089 (14)	0.001 (2)
O8	0.0396 (12)	0.0611 (14)	0.0403 (13)	0.0042 (10)	0.0031 (10)	0.0140 (12)
N1	0.137 (3)	0.079 (3)	0.060 (2)	−0.028 (2)	0.047 (2)	0.015 (2)
N2	0.0420 (14)	0.0562 (16)	0.0387 (15)	0.0089 (12)	0.0067 (12)	0.0188 (13)
N3	0.0435 (17)	0.078 (2)	0.048 (2)	0.0220 (15)	0.0064 (16)	0.0084 (17)
N4	0.107 (3)	0.070 (2)	0.0462 (19)	0.017 (2)	−0.0184 (18)	0.0227 (17)
N5	0.0330 (13)	0.0517 (15)	0.0356 (14)	0.0027 (11)	0.0041 (11)	0.0158 (12)
N6	0.0455 (18)	0.073 (2)	0.049 (2)	−0.0099 (15)	−0.0066 (16)	0.0087 (17)
C1	0.0327 (16)	0.0487 (19)	0.0444 (19)	0.0144 (14)	0.0059 (14)	0.0233 (16)
C2	0.0422 (17)	0.0439 (18)	0.0419 (18)	0.0071 (14)	0.0093 (14)	0.0204 (15)
C3	0.0459 (18)	0.0496 (19)	0.0495 (19)	−0.0011 (14)	0.0016 (15)	0.0224 (16)
C4	0.054 (2)	0.061 (2)	0.060 (2)	−0.0080 (16)	0.0127 (17)	0.0312 (19)
C5	0.084 (3)	0.052 (2)	0.052 (2)	−0.0005 (18)	0.0278 (19)	0.0217 (18)
C6	0.105 (3)	0.055 (2)	0.045 (2)	−0.020 (2)	0.022 (2)	0.0087 (18)
C7	0.068 (2)	0.055 (2)	0.050 (2)	−0.0122 (17)	0.0185 (17)	0.0154 (18)
C8	0.215 (6)	0.108 (4)	0.057 (3)	−0.038 (4)	0.054 (3)	0.012 (3)
C9	0.052 (2)	0.066 (2)	0.0403 (19)	0.0103 (16)	0.0120 (16)	0.0213 (17)
C10	0.054 (2)	0.083 (3)	0.041 (2)	0.0130 (18)	−0.0018 (16)	0.0220 (19)
C11	0.0420 (18)	0.065 (2)	0.047 (2)	0.0130 (15)	−0.0002 (15)	0.0199 (17)
C12	0.0331 (15)	0.0448 (17)	0.0357 (17)	0.0051 (13)	0.0026 (13)	0.0149 (14)
C13	0.0405 (17)	0.057 (2)	0.0330 (17)	0.0088 (14)	0.0019 (14)	0.0163 (15)
C14	0.0361 (17)	0.0513 (19)	0.0422 (19)	0.0084 (14)	0.0035 (15)	0.0123 (16)
C15	0.0321 (16)	0.053 (2)	0.0464 (19)	−0.0002 (14)	0.0020 (14)	0.0266 (17)
C16	0.0391 (16)	0.0417 (17)	0.0414 (18)	0.0016 (13)	−0.0041 (14)	0.0208 (15)
C17	0.0459 (17)	0.0493 (19)	0.0418 (18)	0.0056 (14)	0.0030 (14)	0.0193 (15)
C18	0.0485 (19)	0.053 (2)	0.056 (2)	0.0137 (15)	−0.0057 (16)	0.0263 (18)
C19	0.062 (2)	0.050 (2)	0.044 (2)	0.0020 (16)	−0.0131 (17)	0.0217 (17)
C20	0.084 (3)	0.057 (2)	0.041 (2)	0.0205 (19)	−0.0042 (18)	0.0108 (17)
C21	0.064 (2)	0.051 (2)	0.049 (2)	0.0187 (16)	−0.0065 (17)	0.0167 (17)
C22	0.134 (4)	0.087 (3)	0.046 (2)	0.007 (3)	−0.020 (2)	0.021 (2)
C23	0.0425 (18)	0.065 (2)	0.0356 (17)	−0.0014 (15)	−0.0003 (14)	0.0192 (16)
C24	0.0474 (19)	0.088 (3)	0.0362 (18)	−0.0034 (18)	0.0104 (15)	0.0261 (18)
C25	0.0361 (17)	0.068 (2)	0.0447 (19)	−0.0073 (15)	0.0085 (15)	0.0170 (17)
C26	0.0357 (16)	0.0489 (18)	0.0381 (17)	−0.0016 (13)	0.0039 (13)	0.0120 (15)
C27	0.0402 (17)	0.0529 (19)	0.0339 (17)	0.0028 (14)	0.0089 (14)	0.0125 (15)
C28	0.055 (2)	0.071 (2)	0.043 (2)	−0.0177 (18)	0.0018 (17)	0.0048 (18)

Co1—O1	2.0553 (17)	C3—H3	0.9300
Co1—O1i	2.0553 (17)	C4—C5	1.384 (4)
Co1—O4	2.088 (2)	C4—H4	0.9300
Co1—O4i	2.088 (2)	C5—C6	1.392 (4)
Co1—N2	2.153 (2)	C6—C7	1.381 (4)
Co1—N2i	2.153 (2)	C6—H6	0.9300
Co2—O5	2.0696 (18)	C7—H7	0.9300
Co2—O5ii	2.0696 (18)	C8—H8A	0.9600
Co2—O8	2.129 (2)	C8—H8B	0.9600
Co2—O8ii	2.129 (2)	C8—H8C	0.9600
Co2—N5	2.159 (2)	C9—H9	0.9300
Co2—N5ii	2.159 (2)	C10—C9	1.380 (4)
O1—C1	1.274 (3)	C10—H10	0.9300
O2—C1	1.255 (3)	C11—C10	1.366 (4)
O3—C14	1.229 (3)	C11—H11	0.9300
O4—H41	0.876 (17)	C12—C11	1.381 (4)
O4—H42	0.89 (4)	C12—C14	1.481 (4)
O5—C15	1.276 (3)	C13—C12	1.385 (4)
O6—C15	1.262 (3)	C13—H13	0.9300
O7—C28	1.218 (4)	C15—C16	1.479 (4)
O8—H81	0.907 (14)	C16—C17	1.389 (4)
O8—H82	0.932 (18)	C16—C21	1.382 (4)
N1—C5	1.376 (4)	C17—C18	1.365 (4)
N1—C8	1.428 (5)	C17—H17	0.9300
N1—H1	0.84 (4)	C18—C19	1.389 (4)
N2—C9	1.335 (3)	C18—H18	0.9300
N2—C13	1.330 (3)	C19—C20	1.389 (4)
N3—C14	1.325 (4)	C20—C21	1.375 (4)
N3—H31	0.870 (19)	C20—H20	0.9300
N3—H32	0.909 (19)	C21—H21	0.9300
N4—C19	1.371 (4)	C22—H22A	0.9600
N4—C22	1.430 (5)	C22—H22B	0.9600
N4—H4A	0.87 (2)	C22—H22C	0.9600
N5—C23	1.336 (3)	C23—H23	0.9300
N5—C27	1.331 (3)	C24—C23	1.373 (4)
N6—C28	1.319 (4)	C24—H24	0.9300
N6—H61	0.904 (19)	C25—C24	1.369 (4)
N6—H62	0.878 (19)	C25—H25	0.9300
C1—C2	1.488 (4)	C26—C25	1.383 (4)
C2—C3	1.393 (4)	C26—C28	1.484 (4)
C2—C7	1.371 (4)	C27—C26	1.374 (4)
C3—C4	1.362 (4)	C27—H27	0.9300
O1i—Co1—O1	180.000 (1)	C7—C6—H6	119.9
O1—Co1—O4	92.44 (9)	C2—C7—C6	121.8 (3)
O1i—Co1—O4	87.56 (9)	C2—C7—H7	119.1
O1—Co1—O4i	87.56 (9)	C6—C7—H7	119.1
O1i—Co1—O4i	92.44 (9)	N1—C8—H8A	109.5
O1—Co1—N2	89.34 (8)	N1—C8—H8B	109.5
O1i—Co1—N2	90.66 (8)	N1—C8—H8C	109.5
O1—Co1—N2i	90.66 (8)	H8A—C8—H8B	109.5
O1i—Co1—N2i	89.34 (8)	H8A—C8—H8C	109.5
O4i—Co1—O4	180.00 (9)	H8B—C8—H8C	109.5
O4—Co1—N2	88.05 (10)	N2—C9—C10	122.1 (3)
O4i—Co1—N2	91.95 (10)	N2—C9—H9	118.9
O4—Co1—N2i	91.95 (10)	C10—C9—H9	118.9
O4i—Co1—N2i	88.05 (10)	C9—C10—H10	120.1
N2i—Co1—N2	180.0	C11—C10—C9	119.8 (3)
O5ii—Co2—O5	180.00 (10)	C11—C10—H10	120.1
O5—Co2—O8	90.59 (8)	C10—C11—C12	119.2 (3)
O5ii—Co2—O8	89.41 (8)	C10—C11—H11	120.4
O5—Co2—O8ii	89.41 (8)	C12—C11—H11	120.4
O5ii—Co2—O8ii	90.59 (8)	C11—C12—C13	117.2 (3)
O5—Co2—N5	89.28 (8)	C11—C12—C14	125.2 (3)
O5ii—Co2—N5	90.72 (8)	C13—C12—C14	117.6 (2)
O5—Co2—N5ii	90.72 (8)	N2—C13—C12	124.2 (3)
O5ii—Co2—N5ii	89.28 (8)	N2—C13—H13	117.9
O8ii—Co2—O8	180.00 (12)	C12—C13—H13	117.9
O8—Co2—N5	92.47 (8)	O3—C14—N3	121.5 (3)
O8ii—Co2—N5	87.53 (8)	O3—C14—C12	120.8 (3)
O8—Co2—N5ii	87.53 (8)	N3—C14—C12	117.7 (3)
O8ii—Co2—N5ii	92.47 (8)	O5—C15—C16	117.4 (3)
N5—Co2—N5ii	180.0	O6—C15—O5	123.2 (3)
C1—O1—Co1	128.64 (18)	O6—C15—C16	119.4 (3)
Co1—O4—H41	134 (2)	C17—C16—C15	121.3 (3)
Co1—O4—H42	111 (3)	C21—C16—C17	117.2 (3)
H42—O4—H41	106 (3)	C21—C16—C15	121.5 (3)
C15—O5—Co2	128.33 (19)	C16—C17—H17	119.4
Co2—O8—H81	125 (2)	C18—C17—C16	121.1 (3)
Co2—O8—H82	103 (2)	C18—C17—H17	119.4
H81—O8—H82	106 (2)	C17—C18—C19	121.5 (3)
C5—N1—C8	124.7 (3)	C17—C18—H18	119.2
C5—N1—H1	111 (3)	C19—C18—H18	119.2
C8—N1—H1	124 (3)	N4—C19—C20	121.9 (3)
C9—N2—Co1	123.3 (2)	N4—C19—C18	120.3 (3)
C13—N2—Co1	119.12 (19)	C20—C19—C18	117.7 (3)
C13—N2—C9	117.5 (2)	C19—C20—H20	119.9
C14—N3—H31	118 (2)	C21—C20—C19	120.2 (3)
C14—N3—H32	124 (2)	C21—C20—H20	119.9
H31—N3—H32	118 (3)	C16—C21—H21	118.9
C19—N4—C22	124.4 (3)	C20—C21—C16	122.2 (3)
C19—N4—H4A	116 (3)	C20—C21—H21	118.9
C22—N4—H4A	119 (3)	N4—C22—H22A	109.5
C23—N5—Co2	124.23 (19)	N4—C22—H22B	109.5
C27—N5—Co2	118.79 (18)	N4—C22—H22C	109.5
C27—N5—C23	116.9 (2)	H22A—C22—H22B	109.5
C28—N6—H61	124 (2)	H22A—C22—H22C	109.5
C28—N6—H62	116 (2)	H22B—C22—H22C	109.5
H62—N6—H61	120 (3)	N5—C23—C24	122.7 (3)
O1—C1—C2	116.6 (3)	N5—C23—H23	118.7
O2—C1—O1	124.1 (3)	C24—C23—H23	118.7
O2—C1—C2	119.3 (3)	C23—C24—H24	120.2
C3—C2—C1	121.4 (3)	C25—C24—C23	119.6 (3)
C7—C2—C1	121.1 (3)	C25—C24—H24	120.2
C7—C2—C3	117.5 (3)	C24—C25—C26	118.8 (3)
C2—C3—H3	119.3	C24—C25—H25	120.6
C4—C3—C2	121.3 (3)	C26—C25—H25	120.6
C4—C3—H3	119.3	C25—C26—C28	124.6 (3)
C3—C4—C5	121.2 (3)	C27—C26—C25	117.7 (3)
C3—C4—H4	119.4	C27—C26—C28	117.8 (3)
C5—C4—H4	119.4	N5—C27—C26	124.4 (3)
N1—C5—C4	120.0 (3)	N5—C27—H27	117.8
N1—C5—C6	122.1 (4)	C26—C27—H27	117.8
C4—C5—C6	117.9 (3)	O7—C28—N6	122.2 (3)
C5—C6—H6	119.9	O7—C28—C26	119.5 (3)
C7—C6—C5	120.2 (3)	N6—C28—C26	118.3 (3)
O4i—Co1—O1—C1	36.6 (2)	C1—C2—C3—C4	177.7 (3)
O4—Co1—O1—C1	−143.4 (2)	C7—C2—C3—C4	−1.1 (4)
N2i—Co1—O1—C1	124.6 (2)	C1—C2—C7—C6	−177.9 (3)
N2—Co1—O1—C1	−55.4 (2)	C3—C2—C7—C6	1.0 (5)
O8ii—Co2—O5—C15	32.2 (2)	C2—C3—C4—C5	1.1 (5)
O8—Co2—O5—C15	−147.8 (2)	C3—C4—C5—N1	178.4 (3)
N5—Co2—O5—C15	119.8 (2)	C3—C4—C5—C6	−0.8 (5)
N5ii—Co2—O5—C15	−60.2 (2)	N1—C5—C6—C7	−178.6 (4)
O1i—Co1—N2—C13	138.0 (2)	C4—C5—C6—C7	0.6 (5)
O1—Co1—N2—C13	−42.0 (2)	C5—C6—C7—C2	−0.7 (5)
O4i—Co1—N2—C13	−129.5 (2)	C11—C10—C9—N2	−0.4 (5)
O4—Co1—N2—C13	50.5 (2)	C12—C11—C10—C9	−0.4 (5)
O1i—Co1—N2—C9	−37.7 (2)	C13—C12—C11—C10	0.4 (4)
O1—Co1—N2—C9	142.3 (2)	C14—C12—C11—C10	−179.5 (3)
O4i—Co1—N2—C9	54.8 (2)	C11—C12—C14—O3	170.4 (3)
O4—Co1—N2—C9	−125.2 (2)	C11—C12—C14—N3	−9.6 (4)
O5ii—Co2—N5—C27	33.7 (2)	C13—C12—C14—O3	−9.5 (4)
O5—Co2—N5—C27	−146.3 (2)	C13—C12—C14—N3	170.5 (3)
O8ii—Co2—N5—C27	−56.8 (2)	N2—C13—C12—C11	0.4 (4)
O8—Co2—N5—C27	123.2 (2)	N2—C13—C12—C14	−179.7 (3)
O5ii—Co2—N5—C23	−149.3 (2)	O5—C15—C16—C17	−177.9 (2)
O5—Co2—N5—C23	30.7 (2)	O5—C15—C16—C21	2.4 (4)
O8ii—Co2—N5—C23	120.2 (2)	O6—C15—C16—C17	2.7 (4)
O8—Co2—N5—C23	−59.8 (2)	O6—C15—C16—C21	−177.0 (3)
Co1—O1—C1—O2	−18.0 (4)	C15—C16—C17—C18	179.6 (3)
Co1—O1—C1—C2	162.07 (17)	C21—C16—C17—C18	−0.7 (4)
Co2—O5—C15—O6	−12.4 (4)	C15—C16—C21—C20	−179.6 (3)
Co2—O5—C15—C16	168.20 (17)	C17—C16—C21—C20	0.7 (5)
C8—N1—C5—C4	−179.7 (4)	C16—C17—C18—C19	0.5 (5)
C8—N1—C5—C6	−0.5 (7)	C17—C18—C19—N4	179.3 (3)
Co1—N2—C9—C10	176.9 (2)	C17—C18—C19—C20	−0.1 (5)
C13—N2—C9—C10	1.1 (4)	N4—C19—C20—C21	−179.3 (3)
Co1—N2—C13—C12	−177.1 (2)	C18—C19—C20—C21	0.1 (5)
C9—N2—C13—C12	−1.1 (4)	C19—C20—C21—C16	−0.4 (5)
C22—N4—C19—C18	−178.1 (3)	C25—C24—C23—N5	−1.1 (5)
C22—N4—C19—C20	1.3 (6)	C26—C25—C24—C23	1.4 (5)
Co2—N5—C23—C24	−177.3 (2)	C27—C26—C25—C24	−0.5 (5)
C27—N5—C23—C24	−0.2 (4)	C28—C26—C25—C24	−179.0 (3)
Co2—N5—C27—C26	178.4 (2)	C25—C26—C28—O7	−174.4 (4)
C23—N5—C27—C26	1.2 (4)	C25—C26—C28—N6	7.8 (5)
O1—C1—C2—C3	178.0 (2)	C27—C26—C28—O7	7.1 (5)
O1—C1—C2—C7	−3.1 (4)	C27—C26—C28—N6	−170.7 (3)
O2—C1—C2—C3	−1.9 (4)	N5—C27—C26—C25	−0.9 (5)
O2—C1—C2—C7	176.9 (3)	N5—C27—C26—C28	177.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H41···O7iii	0.88 (2)	1.75 (2)	2.618 (4)	173 (4)
O4—H42···O2i	0.89 (4)	1.86 (4)	2.644 (3)	146 (4)
O8—H81···O3iv	0.91 (2)	1.84 (2)	2.742 (3)	173 (3)
O8—H82···O6ii	0.94 (3)	1.76 (3)	2.648 (3)	156 (3)
N3—H32···O2v	0.91 (3)	2.04 (3)	2.939 (4)	168 (3)
N4—H4A···O4v	0.88 (4)	2.53 (4)	3.288 (4)	145 (3)
N6—H61···O6vi	0.90 (3)	2.08 (3)	2.973 (4)	169 (3)
N6—H62···O3iii	0.88 (3)	2.36 (3)	3.124 (4)	146 (3)

Table 1

Selected bond lengths (Å)

Co1—O1	2.0553 (17)
Co1—O4	2.088 (2)
Co1—N2	2.153 (2)
Co2—O5	2.0696 (18)
Co2—O8	2.129 (2)
Co2—N5	2.159 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H41⋯O7i	0.88 (2)	1.75 (2)	2.618 (4)	173 (4)
O4—H42⋯O2ii	0.89 (4)	1.86 (4)	2.644 (3)	146 (4)
O8—H81⋯O3iii	0.91 (2)	1.84 (2)	2.742 (3)	173 (3)
O8—H82⋯O6iv	0.94 (3)	1.76 (3)	2.648 (3)	156 (3)
N3—H32⋯O2v	0.91 (3)	2.04 (3)	2.939 (4)	168 (3)
N4—H4A⋯O4v	0.88 (4)	2.53 (4)	3.288 (4)	145 (3)
N6—H61⋯O6vi	0.90 (3)	2.08 (3)	2.973 (4)	169 (3)
N6—H62⋯O3i	0.88 (3)	2.36 (3)	3.124 (4)	146 (3)

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