Diaqua-(isonicotinamide-κN)(4-meth-oxy-benzoato-κO,O')(4-meth-oxy-benzoato-κO)cobalt(II).

In the title complex, [Co(C(8)H(7)O(3))(2)(C(6)H(6)N(2)O)(H(2)O)(2)], the Co(II) atom is coordinated by three O atoms from two 4-meth-oxy-benzoate ligands, which act in different modes, viz. monodentate and bidentate, two water mol-ecules and one N atom of the isonicotinamide ligand in a distorted octa-hedral geometry. The monodentate-coordinated carboxyl-ate group is involved in an intra-molecular O-H⋯O hydrogen bond with the coordinated water mol-ecule. In the crystal structure, inter-molecular O-H⋯O and N-H⋯O hydrogen bonds link the mol-ecules into layers parallel to the ab plane. The crystal packing is further stabilized by weak C-H⋯O hydrogen bonds and π-π inter-actions indicated by the short distance of 3.6181 (8) Å between the centroids of the benzene and pyridine rings of neighbouring mol-ecules.

Related literature

For general background to niacin and the nicotinic acid deriv­ative N,N-diethyl­nicotinamide, see: Krishnamachari (1974 ▶) and Bigoli et al. (1972 ▶), respectively. For related structures, see: Greenaway et al. (1984 ▶); Hökelek et al. (2009a ▶,b ▶,c ▶,d ▶); Necefoğlu et al. (2010 ▶).

Experimental

Crystal data

[Co(C8H7O3)2(C6H6N2O)(H2O)2]

M = 519.36

Monoclinic,

a = 8.2666 (2) Å

b = 6.8055 (2) Å

c = 20.5415 (4) Å

β = 99.808 (2)°

V = 1138.74 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.81 mm−1

T = 100 K

0.39 × 0.32 × 0.28 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.739, T max = 0.791

11263 measured reflections

4838 independent reflections

4597 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.050

S = 1.01

4838 reflections

333 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 1761 Friedel pairs

Flack parameter: 0.015 (7)

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/S160053681002194X/cv2727sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002194X/cv2727Isup2.hkl

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

[Co(C8H7O3)2(C6H6N2O)(H2O)2]	F(000) = 538
Mr = 519.36	Dx = 1.515 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 6882 reflections
a = 8.2666 (2) Å	θ = 2.5–28.4°
b = 6.8055 (2) Å	µ = 0.81 mm−1
c = 20.5415 (4) Å	T = 100 K
β = 99.808 (2)°	Block, brown
V = 1138.74 (5) Å3	0.39 × 0.32 × 0.28 mm
Z = 2

Bruker Kappa APEXII CCD area-detector diffractometer	4838 independent reflections
Radiation source: fine-focus sealed tube	4597 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 28.4°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→9
Tmin = 0.739, Tmax = 0.791	k = −8→9
11263 measured reflections	l = −27→27

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.022	w = 1/[σ2(Fo2) + (0.0215P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.050	(Δ/σ)max = 0.003
S = 1.01	Δρmax = 0.29 e Å−3
4838 reflections	Δρmin = −0.24 e Å−3
333 parameters	Absolute structure: Flack (1983), 1761 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.015 (7)
Secondary atom site location: difference Fourier map

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	0.83963 (2)	0.92738 (3)	0.717117 (8)	0.01106 (5)
O1	0.87439 (13)	0.72789 (18)	0.79844 (5)	0.0132 (2)
O2	0.75818 (13)	1.01182 (18)	0.81134 (5)	0.0145 (2)
O3	0.68768 (15)	0.5746 (2)	1.08004 (5)	0.0212 (3)
O4	0.78237 (13)	0.51498 (18)	0.63163 (5)	0.0156 (2)
O5	0.95880 (13)	0.76378 (18)	0.65605 (5)	0.0146 (2)
O6	1.43741 (13)	0.13627 (18)	0.56391 (5)	0.0160 (2)
O7	1.44482 (14)	1.65456 (18)	0.77779 (5)	0.0160 (2)
O8	0.60930 (14)	0.78883 (19)	0.68139 (6)	0.0147 (2)
H81	0.652 (3)	0.692 (4)	0.6668 (10)	0.024 (6)*
H82	0.564 (3)	0.750 (4)	0.7153 (12)	0.052 (7)*
O9	0.72143 (15)	1.1511 (2)	0.66328 (6)	0.0177 (3)
H91	0.639 (2)	1.126 (4)	0.6396 (10)	0.024 (6)*
H92	0.749 (2)	1.277 (4)	0.6543 (9)	0.021 (5)*
N1	1.05301 (16)	1.0966 (2)	0.74674 (6)	0.0127 (3)
N2	1.62169 (17)	1.4016 (3)	0.79899 (7)	0.0175 (3)
H2A	1.643 (2)	1.290 (4)	0.8055 (9)	0.015 (5)*
H2B	1.708 (3)	1.486 (4)	0.8026 (10)	0.033 (6)*
C1	0.80942 (19)	0.8473 (3)	0.83434 (7)	0.0130 (3)
C2	0.79173 (19)	0.7843 (3)	0.90221 (7)	0.0140 (3)
C3	0.86387 (19)	0.6109 (3)	0.92813 (7)	0.0172 (3)
H3	0.9323	0.5420	0.9046	0.021*
C4	0.8362 (2)	0.5378 (3)	0.98853 (7)	0.0190 (4)
H4	0.8862	0.4220	1.0056	0.023*
C5	0.7328 (2)	0.6403 (3)	1.02288 (7)	0.0172 (4)
C6	0.6650 (2)	0.8189 (3)	0.99909 (8)	0.0200 (4)
H6	0.6001	0.8901	1.0235	0.024*
C7	0.69427 (19)	0.8905 (3)	0.93914 (7)	0.0172 (4)
H7	0.6489	1.0099	0.9233	0.021*
C8	0.7330 (2)	0.3780 (3)	1.10016 (8)	0.0238 (4)
H8A	0.6763	0.3397	1.1352	0.036*
H8B	0.8493	0.3718	1.1154	0.036*
H8C	0.7038	0.2906	1.0633	0.036*
C9	0.92278 (19)	0.5941 (2)	0.63394 (7)	0.0125 (3)
C10	1.05374 (18)	0.4757 (2)	0.60954 (7)	0.0122 (4)
C11	1.0197 (2)	0.2936 (3)	0.57978 (7)	0.0160 (3)
H11	0.9117	0.2493	0.5716	0.019*
C12	1.14209 (19)	0.1759 (3)	0.56200 (7)	0.0160 (3)
H12	1.1168	0.0551	0.5416	0.019*
C13	1.30388 (19)	0.2427 (3)	0.57528 (7)	0.0135 (3)
C14	1.33919 (17)	0.4281 (3)	0.60267 (6)	0.0160 (3)
H14	1.4464	0.4749	0.6093	0.019*
C15	1.2158 (2)	0.5421 (3)	0.61986 (7)	0.0148 (3)
H15	1.2406	0.6651	0.6386	0.018*
C16	1.4086 (2)	−0.0503 (3)	0.53119 (7)	0.0191 (4)
H16A	1.5118	−0.1095	0.5271	0.029*
H16B	1.3448	−0.0312	0.4880	0.029*
H16C	1.3501	−0.1347	0.5566	0.029*
C17	1.20276 (19)	1.0299 (3)	0.74076 (7)	0.0156 (3)
H17	1.2125	0.9018	0.7261	0.019*
C18	1.34326 (19)	1.1433 (3)	0.75550 (7)	0.0143 (3)
H18	1.4452	1.0910	0.7518	0.017*
C19	1.32986 (18)	1.3358 (2)	0.77577 (7)	0.0119 (3)
C20	1.17472 (17)	1.4047 (3)	0.78314 (6)	0.0132 (3)
H20	1.1614	1.5323	0.7975	0.016*
C21	1.04258 (19)	1.2809 (3)	0.76878 (7)	0.0145 (3)
H21	0.9402	1.3273	0.7746	0.017*
C22	1.47067 (19)	1.4762 (2)	0.78517 (7)	0.0135 (3)

	U11	U22	U33	U12	U13	U23
Co1	0.00979 (9)	0.00942 (10)	0.01397 (8)	−0.00058 (10)	0.00201 (6)	−0.00009 (9)
O1	0.0127 (5)	0.0116 (6)	0.0158 (5)	0.0014 (5)	0.0036 (4)	−0.0003 (4)
O2	0.0120 (6)	0.0131 (6)	0.0190 (5)	0.0013 (5)	0.0042 (4)	0.0016 (5)
O3	0.0236 (7)	0.0243 (8)	0.0170 (5)	0.0001 (6)	0.0068 (5)	0.0039 (5)
O4	0.0115 (5)	0.0136 (6)	0.0223 (5)	−0.0021 (5)	0.0046 (4)	−0.0018 (5)
O5	0.0133 (5)	0.0123 (6)	0.0191 (5)	−0.0025 (5)	0.0051 (4)	−0.0027 (5)
O6	0.0133 (5)	0.0146 (7)	0.0201 (5)	0.0021 (5)	0.0033 (4)	−0.0031 (5)
O7	0.0144 (6)	0.0106 (6)	0.0237 (5)	0.0000 (5)	0.0057 (4)	−0.0008 (5)
O8	0.0124 (6)	0.0125 (7)	0.0192 (5)	−0.0017 (5)	0.0029 (4)	−0.0006 (5)
O9	0.0139 (6)	0.0125 (7)	0.0246 (6)	−0.0031 (5)	−0.0029 (5)	0.0033 (5)
N1	0.0124 (6)	0.0120 (7)	0.0137 (5)	−0.0005 (6)	0.0024 (5)	0.0007 (5)
N2	0.0111 (6)	0.0087 (9)	0.0324 (7)	−0.0007 (6)	0.0029 (5)	−0.0019 (7)
C1	0.0066 (7)	0.0138 (8)	0.0178 (7)	−0.0038 (6)	0.0000 (6)	−0.0006 (6)
C2	0.0121 (7)	0.0141 (9)	0.0153 (6)	−0.0031 (7)	0.0010 (5)	0.0003 (6)
C3	0.0148 (8)	0.0194 (10)	0.0174 (7)	0.0026 (7)	0.0031 (6)	−0.0007 (7)
C4	0.0178 (8)	0.0183 (10)	0.0202 (7)	0.0026 (7)	0.0015 (6)	0.0033 (7)
C5	0.0148 (8)	0.0226 (10)	0.0139 (6)	−0.0037 (7)	0.0019 (6)	0.0004 (6)
C6	0.0211 (9)	0.0204 (10)	0.0201 (7)	0.0019 (7)	0.0076 (6)	−0.0029 (7)
C7	0.0174 (7)	0.0140 (11)	0.0206 (7)	−0.0004 (7)	0.0042 (6)	−0.0006 (6)
C8	0.0236 (9)	0.0289 (13)	0.0188 (7)	−0.0002 (8)	0.0030 (6)	0.0080 (7)
C9	0.0140 (8)	0.0123 (9)	0.0112 (6)	0.0002 (6)	0.0017 (6)	0.0016 (6)
C10	0.0117 (7)	0.0137 (10)	0.0115 (6)	0.0007 (6)	0.0025 (5)	0.0023 (5)
C11	0.0116 (8)	0.0175 (9)	0.0189 (7)	−0.0026 (7)	0.0025 (6)	−0.0010 (7)
C12	0.0167 (8)	0.0138 (9)	0.0174 (7)	−0.0025 (7)	0.0029 (6)	−0.0037 (6)
C13	0.0150 (8)	0.0143 (9)	0.0116 (6)	0.0008 (7)	0.0031 (5)	0.0004 (6)
C14	0.0126 (6)	0.0170 (8)	0.0187 (6)	−0.0038 (9)	0.0034 (5)	−0.0018 (8)
C15	0.0175 (8)	0.0120 (9)	0.0151 (6)	−0.0023 (7)	0.0031 (6)	−0.0033 (6)
C16	0.0222 (8)	0.0158 (10)	0.0191 (6)	0.0021 (8)	0.0035 (6)	−0.0044 (7)
C17	0.0151 (8)	0.0119 (9)	0.0198 (7)	0.0013 (7)	0.0030 (6)	−0.0024 (6)
C18	0.0101 (7)	0.0135 (9)	0.0200 (7)	0.0021 (7)	0.0047 (6)	−0.0011 (6)
C19	0.0121 (7)	0.0126 (8)	0.0116 (6)	−0.0016 (6)	0.0031 (5)	0.0008 (6)
C20	0.0139 (7)	0.0089 (10)	0.0175 (6)	0.0032 (7)	0.0048 (5)	−0.0019 (6)
C21	0.0122 (8)	0.0142 (9)	0.0178 (7)	0.0008 (7)	0.0047 (6)	−0.0010 (6)
C22	0.0136 (7)	0.0136 (10)	0.0145 (6)	−0.0018 (6)	0.0052 (5)	−0.0022 (5)

Co1—O1	2.1338 (11)	C6—C5	1.392 (3)
Co1—O2	2.2301 (11)	C6—H6	0.9300
Co1—O5	2.0506 (11)	C7—C6	1.383 (2)
Co1—O8	2.1394 (12)	C7—H7	0.9300
Co1—O9	2.0317 (13)	C8—H8A	0.9600
Co1—N1	2.1077 (13)	C8—H8B	0.9600
O1—C1	1.276 (2)	C8—H8C	0.9600
O2—C1	1.260 (2)	C10—C9	1.502 (2)
O3—C5	1.3662 (19)	C10—C11	1.389 (2)
O3—C8	1.431 (2)	C10—C15	1.395 (2)
O4—C9	1.2729 (19)	C11—H11	0.9300
O5—C9	1.258 (2)	C12—C11	1.387 (2)
O6—C13	1.3730 (19)	C12—C13	1.395 (2)
O6—C16	1.437 (2)	C12—H12	0.9300
O7—C22	1.237 (2)	C14—C13	1.392 (3)
O8—H81	0.83 (2)	C14—C15	1.375 (2)
O8—H82	0.89 (3)	C14—H14	0.9300
O9—H91	0.79 (2)	C15—H15	0.9300
O9—H92	0.91 (2)	C16—H16A	0.9600
N1—C17	1.344 (2)	C16—H16B	0.9600
N1—C21	1.342 (2)	C16—H16C	0.9600
N2—C22	1.333 (2)	C17—C18	1.385 (2)
N2—H2A	0.79 (2)	C17—H17	0.9300
N2—H2B	0.91 (2)	C18—H18	0.9300
C2—C1	1.489 (2)	C19—C18	1.385 (2)
C2—C3	1.387 (2)	C19—C20	1.398 (2)
C2—C7	1.398 (2)	C20—H20	0.9300
C3—C4	1.392 (2)	C21—C20	1.371 (2)
C3—H3	0.9300	C21—H21	0.9300
C4—H4	0.9300	C22—C19	1.493 (2)
C5—C4	1.386 (2)
O1—Co1—O2	60.32 (4)	C6—C7—H7	119.8
O1—Co1—O8	88.94 (4)	O3—C8—H8A	109.5
O5—Co1—O1	96.83 (4)	O3—C8—H8B	109.5
O5—Co1—O2	156.69 (4)	O3—C8—H8C	109.5
O5—Co1—O8	92.47 (5)	H8A—C8—H8B	109.5
O5—Co1—N1	90.44 (5)	H8A—C8—H8C	109.5
O8—Co1—O2	91.64 (5)	H8B—C8—H8C	109.5
O9—Co1—O1	153.01 (5)	O4—C9—C10	117.72 (14)
O9—Co1—O2	95.22 (5)	O5—C9—O4	124.05 (14)
O9—Co1—O5	108.09 (5)	O5—C9—C10	118.23 (13)
O9—Co1—O8	79.99 (5)	C11—C10—C9	121.43 (14)
O9—Co1—N1	92.80 (5)	C11—C10—C15	118.24 (15)
N1—Co1—O1	97.30 (5)	C15—C10—C9	120.23 (14)
N1—Co1—O2	88.29 (5)	C10—C11—H11	119.1
N1—Co1—O8	172.76 (5)	C12—C11—C10	121.90 (15)
C1—O1—Co1	91.92 (10)	C12—C11—H11	119.1
C1—O2—Co1	87.97 (10)	C11—C12—C13	118.61 (16)
C5—O3—C8	117.25 (14)	C11—C12—H12	120.7
C9—O5—Co1	127.62 (10)	C13—C12—H12	120.7
C13—O6—C16	118.14 (12)	O6—C13—C14	115.31 (13)
Co1—O8—H81	93.8 (15)	O6—C13—C12	124.54 (15)
Co1—O8—H82	109.5 (15)	C14—C13—C12	120.15 (15)
H81—O8—H82	108 (2)	C13—C14—H14	119.9
Co1—O9—H91	117.3 (17)	C15—C14—C13	120.10 (14)
Co1—O9—H92	134.2 (12)	C15—C14—H14	119.9
H91—O9—H92	108 (2)	C10—C15—H15	119.6
C17—N1—Co1	121.84 (11)	C14—C15—C10	120.90 (16)
C21—N1—Co1	120.64 (11)	C14—C15—H15	119.6
C21—N1—C17	117.40 (14)	O6—C16—H16A	109.5
C22—N2—H2A	125.4 (14)	O6—C16—H16B	109.5
C22—N2—H2B	118.0 (14)	O6—C16—H16C	109.5
H2A—N2—H2B	117 (2)	H16A—C16—H16B	109.5
O1—C1—C2	118.41 (15)	H16A—C16—H16C	109.5
O2—C1—O1	119.79 (14)	H16B—C16—H16C	109.5
O2—C1—C2	121.77 (15)	N1—C17—C18	122.89 (16)
C3—C2—C7	118.77 (14)	N1—C17—H17	118.6
C3—C2—C1	120.01 (15)	C18—C17—H17	118.6
C7—C2—C1	121.09 (15)	C17—C18—H18	120.5
C2—C3—C4	121.42 (16)	C19—C18—C17	119.09 (15)
C2—C3—H3	119.3	C19—C18—H18	120.5
C4—C3—H3	119.3	C18—C19—C20	118.15 (15)
C3—C4—H4	120.6	C18—C19—C22	122.94 (15)
C5—C4—C3	118.90 (17)	C20—C19—C22	118.75 (15)
C5—C4—H4	120.6	C19—C20—H20	120.6
O3—C5—C4	123.71 (17)	C21—C20—C19	118.87 (17)
O3—C5—C6	115.79 (15)	C21—C20—H20	120.6
C4—C5—C6	120.49 (15)	N1—C21—C20	123.53 (15)
C7—C6—C5	119.92 (16)	N1—C21—H21	118.2
C7—C6—H6	120.0	C20—C21—H21	118.2
C5—C6—H6	120.0	O7—C22—N2	122.40 (15)
C2—C7—H7	119.8	O7—C22—C19	119.83 (14)
C6—C7—C2	120.36 (16)	N2—C22—C19	117.72 (15)
O2—Co1—O1—C1	0.09 (8)	C7—C2—C1—O2	10.6 (2)
O5—Co1—O1—C1	175.24 (9)	C3—C2—C1—O1	8.3 (2)
O8—Co1—O1—C1	−92.40 (9)	C7—C2—C1—O1	−167.51 (14)
O9—Co1—O1—C1	−27.20 (15)	C1—C2—C3—C4	−173.46 (15)
N1—Co1—O1—C1	83.91 (9)	C7—C2—C3—C4	2.4 (2)
O1—Co1—O2—C1	−0.10 (8)	C1—C2—C7—C6	173.09 (15)
O5—Co1—O2—C1	−12.36 (15)	C3—C2—C7—C6	−2.8 (2)
O8—Co1—O2—C1	87.75 (9)	C2—C3—C4—C5	0.7 (3)
O9—Co1—O2—C1	167.84 (9)	O3—C5—C4—C3	175.05 (15)
N1—Co1—O2—C1	−99.50 (9)	C6—C5—C4—C3	−3.5 (2)
O1—Co1—O5—C9	60.93 (12)	C7—C6—C5—O3	−175.47 (15)
O2—Co1—O5—C9	71.64 (17)	C7—C6—C5—C4	3.2 (2)
O8—Co1—O5—C9	−28.29 (12)	C2—C7—C6—C5	0.0 (2)
O9—Co1—O5—C9	−108.57 (12)	C11—C10—C9—O4	5.9 (2)
N1—Co1—O5—C9	158.34 (12)	C11—C10—C9—O5	−174.93 (13)
O1—Co1—N1—C17	75.29 (12)	C15—C10—C9—O4	−170.39 (13)
O1—Co1—N1—C21	−108.72 (11)	C15—C10—C9—O5	8.8 (2)
O2—Co1—N1—C17	135.07 (12)	C9—C10—C11—C12	−174.61 (14)
O2—Co1—N1—C21	−48.93 (11)	C15—C10—C11—C12	1.7 (2)
O5—Co1—N1—C17	−21.65 (12)	C9—C10—C15—C14	174.66 (14)
O5—Co1—N1—C21	154.35 (11)	C11—C10—C15—C14	−1.7 (2)
O9—Co1—N1—C17	−129.79 (12)	C13—C12—C11—C10	0.8 (2)
O9—Co1—N1—C21	46.21 (12)	C11—C12—C13—O6	175.92 (14)
Co1—O1—C1—O2	−0.17 (14)	C11—C12—C13—C14	−3.3 (2)
Co1—O1—C1—C2	177.95 (12)	C15—C14—C13—O6	−175.95 (13)
Co1—O2—C1—O1	0.16 (14)	C15—C14—C13—C12	3.3 (2)
Co1—O2—C1—C2	−177.89 (13)	C13—C14—C15—C10	−0.8 (2)
C8—O3—C5—C4	−8.5 (2)	N1—C17—C18—C19	−1.6 (2)
C8—O3—C5—C6	170.10 (14)	C20—C19—C18—C17	2.6 (2)
Co1—O5—C9—O4	19.3 (2)	C22—C19—C18—C17	−172.69 (13)
Co1—O5—C9—C10	−159.84 (9)	C18—C19—C20—C21	−1.3 (2)
C16—O6—C13—C12	5.3 (2)	C22—C19—C20—C21	174.22 (13)
C16—O6—C13—C14	−175.44 (13)	N1—C21—C20—C19	−1.2 (2)
Co1—N1—C17—C18	175.31 (11)	O7—C22—C19—C18	151.80 (15)
C21—N1—C17—C18	−0.8 (2)	N2—C22—C19—C18	−25.7 (2)
Co1—N1—C21—C20	−173.91 (11)	O7—C22—C19—C20	−23.5 (2)
C17—N1—C21—C20	2.3 (2)	N2—C22—C19—C20	158.99 (13)
C3—C2—C1—O2	−173.63 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2i	0.79 (3)	2.11 (3)	2.877 (2)	164.0 (17)
N2—H2B···O1ii	0.91 (3)	2.16 (3)	3.050 (2)	167 (2)
O8—H81···O4	0.83 (3)	1.84 (3)	2.6577 (17)	167 (3)
O8—H82···O7iii	0.89 (2)	1.86 (3)	2.7427 (16)	172 (2)
O9—H91···O6iv	0.786 (19)	2.078 (19)	2.8384 (16)	163 (2)
O9—H92···O4v	0.91 (3)	1.72 (3)	2.6307 (18)	174.1 (15)
C8—H8A···O7vi	0.96	2.53	3.466 (2)	166
C16—H16B···O4vii	0.96	2.52	3.4752 (18)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2i	0.79 (3)	2.11 (3)	2.877 (2)	164.0 (17)
N2—H2B⋯O1ii	0.91 (3)	2.16 (3)	3.050 (2)	167 (2)
O8—H81⋯O4	0.83 (3)	1.84 (3)	2.6577 (17)	167 (3)
O8—H82⋯O7iii	0.89 (2)	1.86 (3)	2.7427 (16)	172 (2)
O9—H91⋯O6iv	0.786 (19)	2.078 (19)	2.8384 (16)	163 (2)
O9—H92⋯O4v	0.91 (3)	1.72 (3)	2.6307 (18)	174.1 (15)
C8—H8A⋯O7vi	0.96	2.53	3.466 (2)	166
C16—H16B⋯O4vii	0.96	2.52	3.4752 (18)	171

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