Diaqua-bis[4-(dimethyl-amino)-benzoato]-κO,O';κO-(isonicotinamide-κN)cobalt(II).

The title Co(II) complex, [Co(C(9)H(10)NO(2))(2)(C(6)H(6)N(2)O)(H(2)O)(2)], contains two 4-dimethyl-amino-benzoate (DMAB) anions, one isonicotinamide (INA) ligand and two coordinated water mol-ecules. One of the DMAB anions acts as a bidentate ligand, while the other is monodentate. The four O atoms in the equatorial plane around the Co atom form a highly distorted square-planar arrangement, while the distorted octa-hedral coordination geometry is completed by the N atom of the INA ligand and the O atom of the second water mol-ecule in the axial positions. An intra-molecular O-H⋯O hydrogen bond between the monodentate-coordinated carboxyl group and a coordinated water mol-ecule results in a six-membered ring with an envelope conformation. The dihedral angles between the carboxyl groups and the adjacent benzene rings are 4.29 (10)° for the monodentate ligand and 2.31 (13)° for the bidentate ligand, while the two benzene rings are oriented at a dihedral angle of 65.02 (5)°. The dihedral angles between the pyridine and benzene rings are 11.21 (5)° for the monodentate ligand and 74.60 (5)° for the bidentate ligand. In the crystal structure, inter-molecular O-H⋯O, O-H⋯N and N-H⋯O hydrogen bonds link the mol-ecules into a supra-molecular structure.

Related literature

For general background, see: Adiwidjaja et al. (1978 ▶); Amiraslanov et al. (1979 ▶); Antolini et al. (1982 ▶); Antsyshkina et al. (1980 ▶); Bigoli et al. (1972 ▶); Catterick et al. (1974 ▶); Chen & Chen (2002 ▶); Hauptmann et al. (2000 ▶); Krishnamachari (1974 ▶); Shnulin et al. (1981 ▶). For related structures, see: Hökelek et al. (1995 ▶, 1997 ▶, 2007 ▶, 2008 ▶); Hökelek & Necefoğlu (1996 ▶, 1997 ▶, 2007 ▶).

Experimental

Crystal data

[Co(n class="CellLine">C9H10NO2)2(C6H6N2O)(H2O)2]

M = 545.45

Triclinic,

a = 6.85550 (10) Å

b = 8.1028 (2) Å

c = 22.4642 (3) Å

α = 90.9180 (10)°

β = 92.965 (2)°

γ = 93.230 (2)°

V = 1243.98 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.74 mm−1

T = 100 K

0.50 × 0.30 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.764, T max = 0.884

21784 measured reflections

6167 independent reflections

5279 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.074

S = 1.04

6167 reflections

353 parameters

6 restraints

H atoms treated by a mixture of independent and n class="Chemical">constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.38 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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809016602/xu2520sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016602/xu2520Isup2.hkl

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

[Co(C9H10NO2)2(C6H6N2O)(H2O)2]	Z = 2
Mr = 545.45	F(000) = 570
Triclinic, P1	Dx = 1.456 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8555 (1) Å	Cell parameters from 9963 reflections
b = 8.1028 (2) Å	θ = 2.5–28.3°
c = 22.4642 (3) Å	µ = 0.74 mm−1
α = 90.918 (1)°	T = 100 K
β = 92.965 (2)°	Block, brown
γ = 93.230 (2)°	0.50 × 0.30 × 0.16 mm
V = 1243.98 (4) Å3

Bruker Kappa APEXII CCD area-detector diffractometer	6167 independent reflections
Radiation source: fine-focus sealed tube	5279 reflections with I > 2σ(I)
graphite	Rint = 0.046
φ and ω scans	θmax = 28.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→6
Tmin = 0.764, Tmax = 0.884	k = −10→10
21784 measured reflections	l = −27→29

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.033P)2 + 0.378P] where P = (Fo2 + 2Fc2)/3
6167 reflections	(Δ/σ)max = 0.001
353 parameters	Δρmax = 0.43 e Å−3
6 restraints	Δρmin = −0.38 e Å−3

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	0.43320 (3)	0.02268 (2)	0.277708 (9)	0.00947 (6)
O1	0.60678 (15)	0.17803 (12)	0.33279 (5)	0.0131 (2)
O2	0.86084 (15)	0.02285 (12)	0.35203 (5)	0.0149 (2)
O3	0.61788 (15)	0.00803 (12)	0.20163 (5)	0.0130 (2)
O4	0.31810 (15)	−0.10110 (12)	0.19727 (5)	0.0131 (2)
O5	−0.30534 (15)	0.58077 (12)	0.23291 (5)	0.0147 (2)
O6	0.21656 (16)	−0.06931 (13)	0.32895 (5)	0.0148 (2)
H61	0.240 (3)	−0.141 (2)	0.3594 (8)	0.039 (6)*
H62	0.100 (3)	−0.028 (3)	0.3359 (10)	0.048 (7)*
O7	0.57303 (16)	−0.18934 (13)	0.31208 (5)	0.0134 (2)
H71	0.688 (2)	−0.137 (2)	0.3264 (9)	0.036 (6)*
H72	0.605 (3)	−0.258 (2)	0.2840 (8)	0.041 (6)*
N1	1.23506 (18)	0.74180 (15)	0.43479 (6)	0.0133 (3)
N2	0.5720 (3)	−0.30713 (19)	−0.06317 (7)	0.0288 (4)
N3	0.25998 (18)	0.22383 (15)	0.25346 (5)	0.0107 (2)
N4	−0.0640 (2)	0.76078 (16)	0.20689 (6)	0.0151 (3)
H41	−0.147 (3)	0.836 (2)	0.2044 (8)	0.018 (5)*
H42	0.060 (3)	0.784 (2)	0.1996 (9)	0.024 (5)*
C1	0.7817 (2)	0.15986 (18)	0.35163 (6)	0.0112 (3)
C2	0.8986 (2)	0.31004 (17)	0.37515 (6)	0.0109 (3)
C3	0.8160 (2)	0.46310 (18)	0.37877 (7)	0.0134 (3)
H3	0.6851	0.4713	0.3667	0.016*
C4	0.9243 (2)	0.60278 (18)	0.39981 (7)	0.0145 (3)
H4	0.8646	0.7027	0.4025	0.017*
C5	1.1227 (2)	0.59587 (17)	0.41723 (6)	0.0113 (3)
C6	1.2061 (2)	0.44248 (18)	0.41310 (7)	0.0136 (3)
H6	1.3376	0.4342	0.4243	0.016*
C7	1.0954 (2)	0.30329 (18)	0.39263 (7)	0.0129 (3)
H7	1.1540	0.2027	0.3905	0.015*
C8	1.1348 (2)	0.86392 (19)	0.46908 (7)	0.0171 (3)
H8A	1.2225	0.9587	0.4781	0.026*
H8B	1.0942	0.8159	0.5055	0.026*
H8C	1.0223	0.8971	0.4461	0.026*
C9	1.4336 (2)	0.7219 (2)	0.45897 (9)	0.0234 (4)
H9A	1.4987	0.8288	0.4665	0.035*
H9B	1.5039	0.6615	0.4308	0.035*
H9C	1.4289	0.6624	0.4955	0.035*
C10	0.4778 (2)	−0.07098 (17)	0.17208 (7)	0.0115 (3)
C11	0.5002 (2)	−0.12862 (18)	0.11039 (7)	0.0142 (3)
C12	0.3496 (2)	−0.21833 (19)	0.07857 (7)	0.0180 (3)
H12	0.2317	−0.2404	0.0964	0.022*
C13	0.3706 (3)	−0.2755 (2)	0.02120 (8)	0.0226 (4)
H13	0.2663	−0.3337	0.0008	0.027*
C14	0.5478 (3)	−0.2470 (2)	−0.00686 (7)	0.0212 (4)
C15	0.7001 (3)	−0.1550 (2)	0.02534 (8)	0.0221 (4)
H15	0.8189	−0.1333	0.0080	0.027*
C16	0.6747 (2)	−0.09685 (19)	0.08242 (7)	0.0175 (3)
H16	0.7766	−0.0350	0.1026	0.021*
C17	0.7573 (3)	−0.2808 (3)	−0.09026 (9)	0.0377 (5)
H17A	0.7532	−0.3397	−0.1278	0.057*
H17B	0.8596	−0.3202	−0.0644	0.057*
H17C	0.7824	−0.1648	−0.0967	0.057*
C18	0.4093 (3)	−0.3871 (2)	−0.09781 (8)	0.0355 (5)
H18A	0.4509	−0.4176	−0.1364	0.053*
H18B	0.3058	−0.3125	−0.1022	0.053*
H18C	0.3631	−0.4844	−0.0778	0.053*
C19	0.3251 (2)	0.38257 (18)	0.25972 (7)	0.0127 (3)
H19	0.4555	0.4059	0.2721	0.015*
C20	0.2078 (2)	0.51366 (18)	0.24869 (7)	0.0130 (3)
H20	0.2596	0.6221	0.2525	0.016*
C21	0.0118 (2)	0.48028 (17)	0.23182 (6)	0.0103 (3)
C22	−0.0572 (2)	0.31584 (17)	0.22533 (7)	0.0114 (3)
H22	−0.1879	0.2891	0.2143	0.014*
C23	0.0708 (2)	0.19348 (17)	0.23553 (7)	0.0118 (3)
H23	0.0243	0.0841	0.2297	0.014*
C24	−0.1314 (2)	0.61288 (17)	0.22363 (7)	0.0117 (3)

	U11	U22	U33	U12	U13	U23
Co1	0.00738 (11)	0.00874 (10)	0.01243 (11)	0.00157 (7)	0.00073 (7)	−0.00010 (7)
O1	0.0090 (5)	0.0130 (5)	0.0173 (6)	0.0029 (4)	−0.0020 (4)	−0.0014 (4)
O2	0.0098 (5)	0.0111 (5)	0.0239 (6)	0.0029 (4)	−0.0005 (4)	0.0000 (4)
O3	0.0104 (5)	0.0124 (5)	0.0160 (6)	0.0000 (4)	0.0006 (4)	−0.0011 (4)
O4	0.0103 (5)	0.0139 (5)	0.0152 (6)	0.0006 (4)	0.0024 (4)	−0.0006 (4)
O5	0.0076 (5)	0.0121 (5)	0.0246 (6)	0.0011 (4)	0.0016 (4)	−0.0013 (4)
O6	0.0102 (6)	0.0172 (5)	0.0182 (6)	0.0052 (4)	0.0041 (5)	0.0056 (4)
O7	0.0101 (6)	0.0119 (5)	0.0185 (6)	0.0029 (4)	0.0006 (5)	−0.0002 (4)
N1	0.0110 (6)	0.0120 (6)	0.0166 (7)	0.0018 (5)	−0.0017 (5)	−0.0023 (5)
N2	0.0426 (10)	0.0311 (8)	0.0138 (7)	0.0097 (7)	0.0043 (7)	−0.0034 (6)
N3	0.0099 (6)	0.0116 (6)	0.0106 (6)	0.0007 (5)	0.0014 (5)	0.0004 (5)
N4	0.0078 (7)	0.0108 (6)	0.0270 (8)	0.0029 (5)	0.0003 (6)	0.0032 (5)
C1	0.0111 (7)	0.0132 (7)	0.0095 (7)	0.0016 (6)	0.0014 (6)	0.0006 (5)
C2	0.0106 (7)	0.0130 (7)	0.0094 (7)	0.0010 (5)	0.0013 (6)	0.0011 (5)
C3	0.0092 (7)	0.0160 (7)	0.0151 (8)	0.0033 (6)	−0.0014 (6)	−0.0006 (6)
C4	0.0138 (8)	0.0121 (7)	0.0179 (8)	0.0041 (6)	0.0006 (6)	−0.0008 (6)
C5	0.0126 (7)	0.0122 (7)	0.0092 (7)	0.0004 (6)	0.0020 (6)	0.0012 (5)
C6	0.0100 (7)	0.0155 (7)	0.0154 (8)	0.0026 (6)	−0.0018 (6)	0.0015 (6)
C7	0.0119 (7)	0.0122 (7)	0.0148 (8)	0.0043 (6)	−0.0003 (6)	0.0008 (6)
C8	0.0209 (9)	0.0145 (7)	0.0159 (8)	0.0026 (6)	0.0009 (7)	−0.0032 (6)
C9	0.0155 (8)	0.0168 (8)	0.0368 (11)	0.0015 (6)	−0.0093 (8)	−0.0055 (7)
C10	0.0118 (7)	0.0080 (6)	0.0150 (8)	0.0027 (5)	0.0007 (6)	0.0019 (5)
C11	0.0161 (8)	0.0127 (7)	0.0141 (8)	0.0031 (6)	0.0013 (6)	0.0010 (6)
C12	0.0164 (8)	0.0199 (8)	0.0177 (8)	0.0020 (6)	0.0016 (7)	−0.0001 (6)
C13	0.0263 (10)	0.0228 (8)	0.0182 (9)	0.0021 (7)	−0.0046 (7)	−0.0023 (7)
C14	0.0322 (10)	0.0190 (8)	0.0133 (8)	0.0090 (7)	0.0016 (7)	0.0016 (6)
C15	0.0234 (9)	0.0249 (9)	0.0194 (9)	0.0053 (7)	0.0087 (7)	0.0028 (7)
C16	0.0187 (8)	0.0171 (7)	0.0171 (8)	0.0016 (6)	0.0025 (7)	0.0015 (6)
C17	0.0527 (14)	0.0452 (12)	0.0177 (10)	0.0161 (10)	0.0122 (9)	−0.0011 (8)
C18	0.0521 (14)	0.0385 (11)	0.0167 (9)	0.0174 (10)	−0.0056 (9)	−0.0080 (8)
C19	0.0090 (7)	0.0134 (7)	0.0155 (8)	−0.0002 (6)	−0.0003 (6)	0.0027 (6)
C20	0.0116 (7)	0.0098 (7)	0.0175 (8)	−0.0018 (5)	0.0002 (6)	0.0012 (6)
C21	0.0093 (7)	0.0120 (7)	0.0101 (7)	0.0022 (5)	0.0024 (6)	0.0011 (5)
C22	0.0089 (7)	0.0128 (7)	0.0123 (7)	−0.0002 (5)	0.0005 (6)	−0.0001 (5)
C23	0.0120 (7)	0.0099 (7)	0.0133 (7)	−0.0003 (5)	0.0007 (6)	−0.0008 (5)
C24	0.0116 (7)	0.0103 (7)	0.0132 (7)	0.0015 (5)	−0.0010 (6)	−0.0019 (5)

Co1—O1	2.0397 (10)	C7—C2	1.390 (2)
Co1—O3	2.1845 (11)	C7—C6	1.382 (2)
Co1—O4	2.1445 (11)	C7—H7	0.9300
Co1—O6	2.0410 (11)	C8—H8A	0.9600
Co1—O7	2.1490 (10)	C8—H8B	0.9600
Co1—N3	2.1314 (12)	C8—H8C	0.9600
Co1—C10	2.5187 (15)	C9—H9A	0.9600
O1—C1	1.2682 (17)	C9—H9B	0.9600
O2—C1	1.2628 (17)	C9—H9C	0.9600
O3—C10	1.2743 (18)	C10—C11	1.473 (2)
O4—C10	1.2716 (18)	C11—C12	1.388 (2)
O5—C24	1.2353 (18)	C11—C16	1.393 (2)
O6—H61	0.919 (14)	C12—C13	1.380 (2)
O6—H62	0.903 (16)	C12—H12	0.9300
O7—H71	0.910 (14)	C13—C14	1.407 (2)
O7—H72	0.881 (15)	C13—H13	0.9300
N1—C5	1.4135 (18)	C15—C14	1.409 (3)
N1—C8	1.4668 (19)	C15—H15	0.9300
N1—C9	1.457 (2)	C16—C15	1.382 (2)
N2—C14	1.370 (2)	C16—H16	0.9300
N2—C17	1.444 (3)	C17—H17A	0.9600
N2—C18	1.443 (3)	C17—H17B	0.9600
N3—C19	1.3405 (19)	C17—H17C	0.9600
N3—C23	1.3456 (19)	C18—H18A	0.9600
N4—C24	1.3269 (19)	C18—H18B	0.9600
N4—H41	0.857 (19)	C18—H18C	0.9600
N4—H42	0.89 (2)	C19—H19	0.9300
C1—C2	1.492 (2)	C20—C19	1.386 (2)
C2—C3	1.395 (2)	C20—C21	1.387 (2)
C3—H3	0.9300	C20—H20	0.9300
C4—C3	1.381 (2)	C22—C21	1.392 (2)
C4—C5	1.401 (2)	C22—C23	1.375 (2)
C4—H4	0.9300	C22—H22	0.9300
C6—C5	1.401 (2)	C23—H23	0.9300
C6—H6	0.9300	C24—C21	1.503 (2)
O1—Co1—O3	100.06 (4)	C5—C4—H4	119.6
O1—Co1—O4	159.45 (4)	O5—C24—N4	122.77 (14)
O1—Co1—O6	105.47 (5)	O5—C24—C21	119.20 (13)
O1—Co1—O7	91.43 (4)	N4—C24—C21	118.02 (13)
O1—Co1—N3	89.64 (4)	C4—C3—C2	121.51 (14)
O1—Co1—C10	130.10 (5)	C4—C3—H3	119.2
O3—Co1—C10	30.39 (4)	C2—C3—H3	119.2
O4—Co1—O7	94.57 (4)	N1—C8—H8A	109.5
O4—Co1—O3	60.70 (4)	N1—C8—H8B	109.5
O4—Co1—C10	30.31 (4)	H8A—C8—H8B	109.5
O6—Co1—O3	152.10 (4)	N1—C8—H8C	109.5
O6—Co1—O4	94.88 (4)	H8A—C8—H8C	109.5
O6—Co1—O7	81.01 (4)	H8B—C8—H8C	109.5
O6—Co1—N3	90.00 (4)	C19—C20—C21	118.85 (13)
O6—Co1—C10	124.14 (5)	C19—C20—H20	120.6
O7—Co1—O3	87.37 (4)	C21—C20—H20	120.6
O7—Co1—C10	91.22 (4)	C15—C16—C11	121.55 (16)
N3—Co1—O3	101.34 (4)	C15—C16—H16	119.2
N3—Co1—O4	87.53 (4)	C11—C16—H16	119.2
N3—Co1—O7	170.90 (4)	C23—C22—C21	118.95 (14)
N3—Co1—C10	95.00 (5)	C23—C22—H22	120.5
C1—O1—Co1	127.70 (9)	C21—C22—H22	120.5
C10—O3—Co1	89.46 (9)	N3—C19—C20	123.23 (14)
C10—O4—Co1	91.35 (9)	N3—C19—H19	118.4
Co1—O7—H71	98.5 (13)	C20—C19—H19	118.4
Co1—O7—H72	113.3 (14)	C12—C13—C14	120.86 (16)
H71—O7—H72	105.6 (18)	C12—C13—H13	119.6
Co1—O6—H61	122.1 (13)	C14—C13—H13	119.6
Co1—O6—H62	129.3 (14)	N3—C23—C22	123.42 (13)
H61—O6—H62	105.6 (18)	N3—C23—H23	118.3
C19—N3—C23	117.19 (12)	C22—C23—H23	118.3
C19—N3—Co1	123.17 (10)	C20—C21—C22	118.31 (13)
C23—N3—Co1	119.40 (9)	C20—C21—C24	123.09 (13)
C5—N1—C9	116.82 (12)	C22—C21—C24	118.51 (13)
C5—N1—C8	116.04 (12)	C4—C5—C6	117.65 (13)
C9—N1—C8	111.97 (13)	C4—C5—N1	120.25 (13)
C24—N4—H42	123.3 (12)	C6—C5—N1	121.99 (14)
C24—N4—H41	116.2 (12)	C14—N2—C18	120.59 (16)
H42—N4—H41	120.5 (17)	C14—N2—C17	120.27 (17)
O4—C10—O3	118.49 (14)	C18—N2—C17	119.00 (15)
O4—C10—C11	120.43 (13)	C16—C15—C14	120.68 (16)
O3—C10—C11	121.07 (13)	C16—C15—H15	119.7
O4—C10—Co1	58.34 (8)	C14—C15—H15	119.7
O3—C10—Co1	60.14 (8)	N2—C14—C13	121.32 (17)
C11—C10—Co1	178.69 (11)	N2—C14—C15	121.24 (17)
O2—C1—O1	123.86 (13)	C13—C14—C15	117.43 (15)
O2—C1—C2	118.69 (13)	N1—C9—H9A	109.5
O1—C1—C2	117.45 (12)	N1—C9—H9B	109.5
C6—C7—C2	121.54 (14)	H9A—C9—H9B	109.5
C6—C7—H7	119.2	N1—C9—H9C	109.5
C2—C7—H7	119.2	H9A—C9—H9C	109.5
C12—C11—C16	117.82 (15)	H9B—C9—H9C	109.5
C12—C11—C10	121.25 (14)	N2—C17—H17A	109.5
C16—C11—C10	120.92 (14)	N2—C17—H17B	109.5
C7—C2—C3	117.57 (13)	H17A—C17—H17B	109.5
C7—C2—C1	121.09 (13)	N2—C17—H17C	109.5
C3—C2—C1	121.31 (13)	H17A—C17—H17C	109.5
C7—C6—C5	120.88 (14)	H17B—C17—H17C	109.5
C7—C6—H6	119.6	N2—C18—H18A	109.5
C5—C6—H6	119.6	N2—C18—H18B	109.5
C13—C12—C11	121.64 (16)	H18A—C18—H18B	109.5
C13—C12—H12	119.2	N2—C18—H18C	109.5
C11—C12—H12	119.2	H18A—C18—H18C	109.5
C3—C4—C5	120.84 (14)	H18B—C18—H18C	109.5
C3—C4—H4	119.6
O1—Co1—O3—C10	−172.09 (8)	C6—C7—C2—C3	0.2 (2)
O6—Co1—O3—C10	31.83 (13)	C6—C7—C2—C1	178.40 (14)
N3—Co1—O3—C10	−80.42 (8)	O2—C1—C2—C7	5.3 (2)
O4—Co1—O3—C10	0.19 (8)	O1—C1—C2—C7	−175.29 (14)
O7—Co1—O3—C10	96.92 (8)	O2—C1—C2—C3	−176.59 (14)
O1—Co1—O4—C10	21.94 (16)	O1—C1—C2—C3	2.8 (2)
O6—Co1—O4—C10	−165.93 (8)	C2—C7—C6—C5	0.3 (2)
N3—Co1—O4—C10	104.28 (8)	C16—C11—C12—C13	0.3 (2)
O7—Co1—O4—C10	−84.59 (8)	C10—C11—C12—C13	−178.73 (14)
O3—Co1—O4—C10	−0.19 (8)	C5—C4—C3—C2	1.3 (2)
O6—Co1—O1—C1	112.48 (12)	C7—C2—C3—C4	−1.0 (2)
N3—Co1—O1—C1	−157.62 (12)	C1—C2—C3—C4	−179.19 (14)
O4—Co1—O1—C1	−75.66 (17)	C12—C11—C16—C15	−1.3 (2)
O7—Co1—O1—C1	31.42 (12)	C10—C11—C16—C15	177.74 (14)
O3—Co1—O1—C1	−56.16 (12)	C23—N3—C19—C20	0.0 (2)
C10—Co1—O1—C1	−61.38 (13)	Co1—N3—C19—C20	−174.44 (11)
O1—Co1—N3—C19	21.32 (12)	C21—C20—C19—N3	1.8 (2)
O6—Co1—N3—C19	126.79 (12)	C11—C12—C13—C14	1.1 (2)
O4—Co1—N3—C19	−138.32 (12)	C19—N3—C23—C22	−2.0 (2)
O3—Co1—N3—C19	−78.86 (12)	Co1—N3—C23—C22	172.64 (11)
C10—Co1—N3—C19	−108.92 (12)	C21—C22—C23—N3	2.2 (2)
O1—Co1—N3—C23	−152.97 (11)	C19—C20—C21—C22	−1.5 (2)
O6—Co1—N3—C23	−47.50 (11)	C19—C20—C21—C24	174.91 (14)
O4—Co1—N3—C23	47.38 (11)	C23—C22—C21—C20	−0.3 (2)
O3—Co1—N3—C23	106.84 (11)	C23—C22—C21—C24	−176.92 (13)
C10—Co1—N3—C23	76.79 (11)	O5—C24—C21—C20	−150.39 (15)
Co1—O4—C10—O3	0.33 (13)	N4—C24—C21—C20	29.2 (2)
Co1—O4—C10—C11	179.46 (12)	O5—C24—C21—C22	26.1 (2)
Co1—O3—C10—O4	−0.32 (13)	N4—C24—C21—C22	−154.32 (14)
Co1—O3—C10—C11	−179.45 (12)	C3—C4—C5—C6	−0.6 (2)
O1—Co1—C10—O4	−170.13 (7)	C3—C4—C5—N1	175.64 (14)
O6—Co1—C10—O4	17.01 (10)	C7—C6—C5—C4	−0.1 (2)
N3—Co1—C10—O4	−76.38 (8)	C7—C6—C5—N1	−176.35 (14)
O7—Co1—C10—O4	96.97 (8)	C9—N1—C5—C4	172.91 (14)
O3—Co1—C10—O4	179.67 (13)	C8—N1—C5—C4	37.38 (19)
O1—Co1—C10—O3	10.20 (10)	C9—N1—C5—C6	−11.0 (2)
O6—Co1—C10—O3	−162.65 (7)	C8—N1—C5—C6	−146.50 (14)
N3—Co1—C10—O3	103.95 (8)	C11—C16—C15—C14	0.9 (2)
O4—Co1—C10—O3	−179.67 (13)	C18—N2—C14—C13	6.5 (2)
O7—Co1—C10—O3	−82.70 (8)	C17—N2—C14—C13	−177.97 (16)
Co1—O1—C1—O2	−19.4 (2)	C18—N2—C14—C15	−173.96 (16)
Co1—O1—C1—C2	161.23 (10)	C17—N2—C14—C15	1.6 (2)
O4—C10—C11—C12	−0.8 (2)	C12—C13—C14—N2	178.18 (15)
O3—C10—C11—C12	178.35 (13)	C12—C13—C14—C15	−1.4 (2)
O4—C10—C11—C16	−179.76 (13)	C16—C15—C14—N2	−179.16 (15)
O3—C10—C11—C16	−0.6 (2)	C16—C15—C14—C13	0.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H41···O3i	0.857 (18)	2.189 (19)	3.0426 (17)	173.8 (17)
N4—H42···O4ii	0.88 (2)	1.96 (2)	2.8101 (17)	161.9 (16)
O6—H61···N1iii	0.92 (2)	1.96 (2)	2.8494 (17)	164 (2)
O6—H62···O2iv	0.90 (2)	1.77 (2)	2.6640 (15)	172 (2)
O7—H71···O2	0.91 (2)	1.77 (2)	2.6532 (15)	161 (2)
O7—H72···O5v	0.88 (2)	1.88 (2)	2.7478 (15)	172 (2)

Table 1

Selected bond lengths (Å)

Co1—O1	2.0397 (10)
Co1—O3	2.1845 (11)
Co1—O4	2.1445 (11)
Co1—O6	2.0410 (11)
Co1—O7	2.1490 (10)
Co1—N3	2.1314 (12)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H41⋯O3i	0.857 (18)	2.189 (19)	3.0426 (17)	173.8 (17)
N4—H42⋯O4ii	0.88 (2)	1.96 (2)	2.8101 (17)	161.9 (16)
O6—H61⋯N1iii	0.918 (17)	1.956 (18)	2.8494 (17)	163.9 (17)
O6—H62⋯O2iv	0.90 (2)	1.77 (2)	2.6640 (15)	172 (2)
O7—H71⋯O2	0.914 (15)	1.774 (16)	2.6532 (15)	160.5 (15)
O7—H72⋯O5v	0.879 (18)	1.875 (18)	2.7478 (15)	171.6 (17)

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