Piperazine-1,4-diium bis-(pyridine-2,6-dicarboxyl-ato-κO,N,O)cobaltate(II) tetra-hydrate.

The asymmetric unit of the title complex, (C(4)H(12)N(2))[Co(C(7)H(3)NO(4))(2)]·4H(2)O, consists of one piperazinediium dication, one [Co(py-2,6-dc)(2)](2-) dianion (where py-2,6-dc is pyridine-2,6-dicarboxyl-ate) and four water mol-ecules. The piperazinediium cation adopts a chair conformation and the Co(II) ion is six-coordinated in an N(2)O(4) environment, having a distorted octa-hedral geometry. In the crystal, inter-molecular O-H⋯O, N-H⋯O and weak C-H⋯O hydrogen bonds link the components, forming a three-dimensional network.

Related literature

The structure determination of title compound was performed as a part of our project on the synthesis of new proton-transfer compounds, see: Raissi Shabari et al. (2010 ▶). For bond lengths in a related cobaltate(II) complex, see: Pasdar et al. (2011 ▶). For bond lengths and angles in the piperazinediium dication, see: Sutherland & Harrison (2009 ▶); Allen et al. (1995 ▶). For positive-charge-assisted hydrogen bonds, see: Gilli et al. (1994 ▶).

Experimental

Crystal data

(C4H12N2)[Co(C7H3NO4)2]·4H2O

M = 549.36

Monoclinic,

a = 7.9537 (16) Å

b = 13.420 (3) Å

c = 21.004 (4) Å

β = 90.55 (3)°

V = 2241.8 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.84 mm−1

T = 150 K

0.5 × 0.40 × 0.15 mm

Data collection

Stoe IPDS 2T diffractometer

Absorption correction: numerical [shape of crystal determined optically (X-RED and X-SHAPE; Stoe & Cie, 2005 ▶)] T min = 0.670, T max = 0.878

15339 measured reflections

6018 independent reflections

5226 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.077

S = 1.07

6018 reflections

364 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.33 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; 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 enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811023518/lh5266sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023518/lh5266Isup2.hkl

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

(C4H12N2)[Co(C7H3NO4)2]·4H2O	F(000) = 1140
Mr = 549.36	Dx = 1.628 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6018 reflections
a = 7.9537 (16) Å	θ = 2.5–29.1°
b = 13.420 (3) Å	µ = 0.84 mm−1
c = 21.004 (4) Å	T = 150 K
β = 90.55 (3)°	Plate, pink
V = 2241.8 (8) Å3	0.5 × 0.4 × 0.15 mm
Z = 4

Stoe IPDS 2T diffractometer	6018 independent reflections
Radiation source: fine-focus sealed tube	5226 reflections with I > 2σ(I)
graphite	Rint = 0.038
Detector resolution: 0.15 mm pixels mm-1	θmax = 29.1°, θmin = 2.5°
rotation method scans	h = −10→10
Absorption correction: numerical shape of crystal determined optically	k = −16→18
Tmin = 0.670, Tmax = 0.878	l = −24→28
15339 measured reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0326P)2 + 1.2111P] where P = (Fo2 + 2Fc2)/3
6018 reflections	(Δ/σ)max = 0.001
364 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.33 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
O10	0.26226 (16)	0.55638 (11)	0.28084 (7)	0.0288 (3)
Co1	0.73056 (2)	0.745668 (14)	0.504511 (9)	0.01278 (6)
C18	1.08242 (19)	0.81672 (13)	0.23202 (8)	0.0195 (3)
H18A	1.1280	0.7659	0.2043	0.023*
H18B	1.1624	0.8712	0.2344	0.023*
C16	0.76380 (18)	0.73170 (12)	0.26866 (7)	0.0173 (3)
H16A	0.6828	0.6777	0.2667	0.021*
H16B	0.7185	0.7836	0.2957	0.021*
C15	0.92728 (19)	0.69397 (11)	0.29675 (7)	0.0176 (3)
H15A	0.9091	0.6714	0.3400	0.021*
H15B	0.9670	0.6378	0.2720	0.021*
C17	0.9172 (2)	0.85410 (12)	0.20509 (8)	0.0197 (3)
H17A	0.8759	0.9083	0.2311	0.024*
H17B	0.9339	0.8793	0.1623	0.024*
N4	0.79141 (16)	0.77200 (10)	0.20359 (6)	0.0165 (2)
N3	1.05640 (16)	0.77441 (11)	0.29680 (6)	0.0175 (3)
O5	0.91680 (15)	0.73565 (8)	0.58111 (5)	0.0206 (2)
N1	0.71594 (14)	0.89536 (9)	0.51050 (6)	0.0128 (2)
O4	0.53764 (14)	0.77007 (8)	0.57578 (5)	0.0188 (2)
O2	0.89349 (14)	0.79723 (8)	0.43015 (5)	0.0191 (2)
O8	0.57909 (14)	0.68290 (8)	0.42961 (5)	0.0187 (2)
C7	0.53098 (18)	0.85856 (11)	0.59591 (7)	0.0145 (3)
C6	0.62806 (17)	0.93522 (11)	0.55788 (7)	0.0132 (3)
C9	0.86203 (17)	0.56523 (11)	0.56247 (7)	0.0128 (3)
C13	0.69018 (17)	0.53516 (11)	0.47424 (7)	0.0124 (3)
O3	0.44917 (14)	0.88780 (9)	0.64298 (5)	0.0190 (2)
O1	0.95932 (14)	0.93309 (8)	0.37446 (5)	0.0188 (2)
O7	0.51331 (14)	0.53761 (9)	0.38257 (6)	0.0218 (2)
N2	0.76472 (14)	0.59801 (9)	0.51494 (6)	0.0116 (2)
C14	0.58397 (18)	0.58788 (11)	0.42379 (7)	0.0148 (3)
C8	0.94256 (18)	0.64790 (11)	0.60154 (7)	0.0149 (3)
C2	0.80213 (17)	0.95197 (11)	0.46993 (7)	0.0128 (3)
C5	0.62615 (19)	1.03742 (11)	0.56736 (7)	0.0159 (3)
H5	0.5664	1.0652	0.6008	0.019*
C12	0.71303 (17)	0.43292 (11)	0.47966 (7)	0.0147 (3)
H12	0.6622	0.3892	0.4510	0.018*
C10	0.88885 (18)	0.46439 (11)	0.57169 (7)	0.0163 (3)
H10	0.9551	0.4417	0.6054	0.020*
C1	0.89276 (17)	0.89032 (11)	0.42059 (7)	0.0147 (3)
C3	0.80328 (18)	1.05509 (11)	0.47560 (7)	0.0151 (3)
H3	0.8610	1.0946	0.4468	0.018*
C11	0.81438 (18)	0.39770 (11)	0.52927 (7)	0.0169 (3)
H11	0.8322	0.3296	0.5340	0.020*
C4	0.71541 (19)	1.09736 (11)	0.52577 (8)	0.0172 (3)
H4	0.7165	1.1661	0.5315	0.021*
O9	0.37881 (15)	0.76948 (10)	0.33746 (7)	0.0244 (3)
O6	1.02757 (14)	0.62407 (9)	0.64909 (6)	0.0223 (2)
O11	0.9680 (2)	0.87887 (11)	0.67821 (7)	0.0312 (3)
O12	0.46115 (18)	0.06341 (10)	0.71858 (6)	0.0260 (3)
H3B	1.157 (3)	0.7514 (16)	0.3122 (11)	0.029 (6)*
H4B	0.828 (3)	0.7228 (18)	0.1787 (11)	0.029 (6)*
H3A	1.022 (3)	0.8243 (18)	0.3232 (11)	0.031 (6)*
H4A	0.694 (3)	0.7923 (19)	0.1846 (11)	0.034 (6)*
H9B	0.437 (3)	0.7419 (18)	0.3625 (12)	0.031 (6)*
H10B	0.324 (4)	0.561 (2)	0.3103 (15)	0.050 (8)*
H10A	0.321 (3)	0.582 (2)	0.2501 (14)	0.051 (8)*
H9A	0.432 (4)	0.815 (2)	0.3200 (14)	0.052 (8)*
H12A	0.508 (3)	0.050 (2)	0.7517 (14)	0.051 (8)*
H12B	0.464 (3)	0.013 (2)	0.6991 (14)	0.045 (8)*
H11B	0.950 (3)	0.838 (2)	0.6492 (14)	0.046 (7)*
H11A	0.989 (3)	0.929 (2)	0.6591 (13)	0.046 (7)*

	U11	U22	U33	U12	U13	U23
O10	0.0222 (6)	0.0391 (8)	0.0252 (7)	−0.0005 (5)	−0.0045 (5)	0.0017 (6)
Co1	0.01592 (9)	0.00943 (9)	0.01298 (10)	0.00047 (7)	−0.00079 (6)	0.00003 (7)
C18	0.0185 (7)	0.0244 (8)	0.0158 (7)	−0.0038 (6)	0.0021 (5)	−0.0007 (6)
C16	0.0154 (6)	0.0188 (7)	0.0177 (7)	0.0008 (5)	0.0014 (5)	−0.0008 (5)
C15	0.0211 (7)	0.0161 (7)	0.0156 (7)	0.0040 (5)	−0.0001 (5)	0.0027 (5)
C17	0.0262 (8)	0.0165 (7)	0.0165 (7)	−0.0008 (6)	−0.0016 (6)	0.0040 (6)
N4	0.0158 (6)	0.0190 (6)	0.0147 (6)	0.0039 (5)	−0.0044 (5)	0.0003 (5)
N3	0.0149 (6)	0.0247 (7)	0.0128 (6)	0.0044 (5)	−0.0024 (5)	−0.0024 (5)
O5	0.0275 (6)	0.0138 (5)	0.0202 (5)	−0.0027 (4)	−0.0086 (4)	−0.0010 (4)
N1	0.0126 (5)	0.0118 (5)	0.0140 (6)	0.0001 (4)	0.0003 (4)	0.0004 (4)
O4	0.0240 (5)	0.0130 (5)	0.0194 (5)	−0.0025 (4)	0.0056 (4)	−0.0011 (4)
O2	0.0243 (5)	0.0142 (5)	0.0188 (5)	0.0013 (4)	0.0063 (4)	−0.0001 (4)
O8	0.0235 (5)	0.0147 (5)	0.0177 (5)	0.0013 (4)	−0.0082 (4)	0.0011 (4)
C7	0.0156 (6)	0.0153 (7)	0.0126 (6)	−0.0003 (5)	−0.0003 (5)	0.0021 (5)
C6	0.0149 (6)	0.0127 (6)	0.0120 (6)	0.0004 (5)	0.0000 (5)	0.0002 (5)
C9	0.0113 (6)	0.0143 (6)	0.0129 (6)	−0.0016 (5)	−0.0012 (5)	0.0005 (5)
C13	0.0113 (6)	0.0139 (6)	0.0120 (6)	0.0000 (5)	−0.0007 (5)	−0.0011 (5)
O3	0.0236 (5)	0.0180 (5)	0.0154 (5)	−0.0002 (4)	0.0067 (4)	0.0003 (4)
O1	0.0230 (5)	0.0181 (5)	0.0154 (5)	−0.0018 (4)	0.0053 (4)	0.0013 (4)
O7	0.0243 (6)	0.0231 (6)	0.0179 (5)	0.0034 (4)	−0.0092 (4)	−0.0060 (4)
N2	0.0111 (5)	0.0121 (5)	0.0117 (5)	−0.0002 (4)	−0.0005 (4)	0.0004 (4)
C14	0.0140 (6)	0.0180 (7)	0.0123 (6)	0.0026 (5)	−0.0014 (5)	0.0002 (5)
C8	0.0137 (6)	0.0170 (7)	0.0139 (6)	−0.0036 (5)	−0.0013 (5)	−0.0015 (5)
C2	0.0120 (6)	0.0138 (6)	0.0124 (6)	0.0002 (5)	−0.0004 (5)	0.0012 (5)
C5	0.0191 (6)	0.0145 (7)	0.0141 (6)	0.0000 (5)	0.0005 (5)	−0.0031 (5)
C12	0.0143 (6)	0.0124 (6)	0.0173 (7)	−0.0019 (5)	−0.0009 (5)	−0.0031 (5)
C10	0.0152 (6)	0.0163 (7)	0.0174 (7)	0.0002 (5)	−0.0033 (5)	0.0045 (5)
C1	0.0133 (6)	0.0168 (7)	0.0142 (6)	−0.0007 (5)	−0.0003 (5)	−0.0014 (5)
C3	0.0160 (6)	0.0126 (6)	0.0168 (7)	−0.0020 (5)	−0.0004 (5)	0.0018 (5)
C11	0.0178 (6)	0.0109 (6)	0.0221 (7)	0.0002 (5)	−0.0009 (6)	0.0024 (5)
C4	0.0204 (7)	0.0109 (6)	0.0202 (7)	−0.0016 (5)	−0.0003 (6)	−0.0007 (5)
O9	0.0182 (5)	0.0233 (6)	0.0315 (7)	0.0007 (5)	−0.0089 (5)	0.0059 (5)
O6	0.0243 (5)	0.0227 (6)	0.0196 (6)	−0.0062 (4)	−0.0116 (4)	0.0031 (5)
O11	0.0541 (9)	0.0202 (6)	0.0195 (6)	−0.0074 (6)	0.0038 (6)	−0.0005 (5)
O12	0.0400 (7)	0.0204 (6)	0.0175 (6)	0.0034 (5)	−0.0031 (5)	−0.0012 (5)

O10—H10B	0.79 (3)	O8—C14	1.2817 (19)
O10—H10A	0.87 (3)	C7—O3	1.2518 (19)
Co1—N2	2.0117 (13)	C7—C6	1.518 (2)
Co1—N1	2.0162 (13)	C6—C5	1.386 (2)
Co1—O8	2.1446 (12)	C9—N2	1.3321 (18)
Co1—O2	2.1532 (13)	C9—C10	1.383 (2)
Co1—O4	2.1787 (13)	C9—C8	1.518 (2)
Co1—O5	2.1807 (13)	C13—N2	1.3357 (18)
C18—N3	1.491 (2)	C13—C12	1.389 (2)
C18—C17	1.511 (2)	C13—C14	1.5229 (19)
C18—H18A	0.9700	O1—C1	1.2485 (19)
C18—H18B	0.9700	O7—C14	1.2293 (18)
C16—N4	1.488 (2)	C8—O6	1.2426 (18)
C16—C15	1.510 (2)	C2—C3	1.389 (2)
C16—H16A	0.9700	C2—C1	1.514 (2)
C16—H16B	0.9700	C5—C4	1.388 (2)
C15—N3	1.490 (2)	C5—H5	0.9300
C15—H15A	0.9700	C12—C11	1.394 (2)
C15—H15B	0.9700	C12—H12	0.9300
C17—N4	1.488 (2)	C10—C11	1.391 (2)
C17—H17A	0.9700	C10—H10	0.9300
C17—H17B	0.9700	C3—C4	1.391 (2)
N4—H4B	0.89 (2)	C3—H3	0.9300
N4—H4A	0.91 (2)	C11—H11	0.9300
N3—H3B	0.91 (2)	C4—H4	0.9300
N3—H3A	0.91 (2)	O9—H9B	0.79 (3)
O5—C8	1.2692 (19)	O9—H9A	0.83 (3)
N1—C6	1.3335 (19)	O11—H11B	0.83 (3)
N1—C2	1.3358 (19)	O11—H11A	0.81 (3)
O4—C7	1.2619 (18)	O12—H12A	0.80 (3)
O2—C1	1.2652 (19)	O12—H12B	0.79 (3)
H10B—O10—H10A	103 (3)	C6—N1—Co1	118.50 (10)
N2—Co1—N1	169.23 (5)	C2—N1—Co1	119.77 (10)
N2—Co1—O8	76.55 (5)	C7—O4—Co1	113.82 (10)
N1—Co1—O8	113.87 (5)	C1—O2—Co1	115.50 (10)
N2—Co1—O2	108.30 (5)	C14—O8—Co1	116.32 (9)
N1—Co1—O2	76.15 (5)	O3—C7—O4	125.69 (14)
O8—Co1—O2	86.10 (5)	O3—C7—C6	118.30 (13)
N2—Co1—O4	99.70 (5)	O4—C7—C6	115.99 (13)
N1—Co1—O4	76.46 (5)	N1—C6—C5	120.71 (14)
O8—Co1—O4	99.71 (5)	N1—C6—C7	113.19 (12)
O2—Co1—O4	151.99 (4)	C5—C6—C7	126.06 (13)
N2—Co1—O5	76.63 (4)	N2—C9—C10	121.04 (13)
N1—Co1—O5	93.13 (4)	N2—C9—C8	113.76 (13)
O8—Co1—O5	152.85 (4)	C10—C9—C8	125.15 (13)
O2—Co1—O5	98.38 (5)	N2—C13—C12	120.96 (13)
O4—Co1—O5	88.87 (5)	N2—C13—C14	113.07 (12)
N3—C18—C17	109.89 (13)	C12—C13—C14	125.97 (13)
N3—C18—H18A	109.7	C9—N2—C13	121.49 (13)
C17—C18—H18A	109.7	C9—N2—Co1	118.93 (10)
N3—C18—H18B	109.7	C13—N2—Co1	119.58 (10)
C17—C18—H18B	109.7	O7—C14—O8	126.80 (14)
H18A—C18—H18B	108.2	O7—C14—C13	118.81 (13)
N4—C16—C15	110.28 (12)	O8—C14—C13	114.39 (12)
N4—C16—H16A	109.6	O6—C8—O5	126.53 (14)
C15—C16—H16A	109.6	O6—C8—C9	118.02 (13)
N4—C16—H16B	109.6	O5—C8—C9	115.43 (13)
C15—C16—H16B	109.6	N1—C2—C3	120.99 (14)
H16A—C16—H16B	108.1	N1—C2—C1	112.12 (12)
N3—C15—C16	110.38 (12)	C3—C2—C1	126.89 (13)
N3—C15—H15A	109.6	C6—C5—C4	118.47 (14)
C16—C15—H15A	109.6	C6—C5—H5	120.8
N3—C15—H15B	109.6	C4—C5—H5	120.8
C16—C15—H15B	109.6	C13—C12—C11	118.08 (13)
H15A—C15—H15B	108.1	C13—C12—H12	121.0
N4—C17—C18	110.13 (13)	C11—C12—H12	121.0
N4—C17—H17A	109.6	C9—C10—C11	118.40 (13)
C18—C17—H17A	109.6	C9—C10—H10	120.8
N4—C17—H17B	109.6	C11—C10—H10	120.8
C18—C17—H17B	109.6	O1—C1—O2	125.15 (14)
H17A—C17—H17B	108.1	O1—C1—C2	119.23 (13)
C16—N4—C17	110.77 (12)	O2—C1—C2	115.62 (13)
C16—N4—H4B	108.8 (15)	C2—C3—C4	117.93 (14)
C17—N4—H4B	109.6 (15)	C2—C3—H3	121.0
C16—N4—H4A	112.4 (15)	C4—C3—H3	121.0
C17—N4—H4A	110.8 (16)	C10—C11—C12	120.02 (14)
H4B—N4—H4A	104 (2)	C10—C11—H11	120.0
C15—N3—C18	112.15 (12)	C12—C11—H11	120.0
C15—N3—H3B	110.8 (14)	C5—C4—C3	120.28 (14)
C18—N3—H3B	109.0 (14)	C5—C4—H4	119.9
C15—N3—H3A	108.6 (14)	C3—C4—H4	119.9
C18—N3—H3A	108.7 (15)	H9B—O9—H9A	110 (2)
H3B—N3—H3A	107 (2)	H11B—O11—H11A	103 (3)
C8—O5—Co1	114.39 (9)	H12A—O12—H12B	104 (3)
C6—N1—C2	121.59 (13)
N4—C16—C15—N3	56.04 (16)	C8—C9—N2—Co1	−2.77 (16)
N3—C18—C17—N4	−57.15 (17)	C12—C13—N2—C9	−0.7 (2)
C15—C16—N4—C17	−58.43 (16)	C14—C13—N2—C9	179.69 (12)
C18—C17—N4—C16	59.08 (16)	C12—C13—N2—Co1	179.15 (11)
C16—C15—N3—C18	−55.72 (17)	C14—C13—N2—Co1	−0.48 (16)
C17—C18—N3—C15	56.17 (17)	N1—Co1—N2—C9	−12.6 (3)
N2—Co1—O5—C8	−8.50 (11)	O8—Co1—N2—C9	−178.50 (11)
N1—Co1—O5—C8	168.13 (11)	O2—Co1—N2—C9	100.29 (11)
O8—Co1—O5—C8	−17.59 (17)	O4—Co1—N2—C9	−80.74 (11)
O2—Co1—O5—C8	−115.43 (11)	O5—Co1—N2—C9	5.75 (10)
O4—Co1—O5—C8	91.75 (11)	N1—Co1—N2—C13	167.6 (2)
N2—Co1—N1—C6	−59.3 (3)	O8—Co1—N2—C13	1.66 (10)
O8—Co1—N1—C6	105.67 (11)	O2—Co1—N2—C13	−79.55 (11)
O2—Co1—N1—C6	−175.04 (11)	O4—Co1—N2—C13	99.42 (11)
O4—Co1—N1—C6	10.90 (10)	O5—Co1—N2—C13	−174.09 (11)
O5—Co1—N1—C6	−77.18 (11)	Co1—O8—C14—O7	−176.49 (13)
N2—Co1—N1—C2	116.5 (3)	Co1—O8—C14—C13	3.39 (16)
O8—Co1—N1—C2	−78.56 (11)	N2—C13—C14—O7	177.88 (14)
O2—Co1—N1—C2	0.73 (10)	C12—C13—C14—O7	−1.7 (2)
O4—Co1—N1—C2	−173.33 (11)	N2—C13—C14—O8	−2.00 (18)
O5—Co1—N1—C2	98.59 (11)	C12—C13—C14—O8	178.38 (14)
N2—Co1—O4—C7	156.74 (10)	Co1—O5—C8—O6	−171.44 (13)
N1—Co1—O4—C7	−12.98 (10)	Co1—O5—C8—C9	9.52 (16)
O8—Co1—O4—C7	−125.39 (10)	N2—C9—C8—O6	175.91 (13)
O2—Co1—O4—C7	−25.34 (16)	C10—C9—C8—O6	−6.8 (2)
O5—Co1—O4—C7	80.51 (11)	N2—C9—C8—O5	−4.96 (19)
N2—Co1—O2—C1	−176.16 (10)	C10—C9—C8—O5	172.35 (14)
N1—Co1—O2—C1	−6.37 (10)	C6—N1—C2—C3	−0.1 (2)
O8—Co1—O2—C1	109.39 (11)	Co1—N1—C2—C3	−175.70 (10)
O4—Co1—O2—C1	6.00 (17)	C6—N1—C2—C1	179.60 (12)
O5—Co1—O2—C1	−97.55 (11)	Co1—N1—C2—C1	3.96 (15)
N2—Co1—O8—C14	−2.85 (11)	N1—C6—C5—C4	1.1 (2)
N1—Co1—O8—C14	180.00 (10)	C7—C6—C5—C4	−176.42 (13)
O2—Co1—O8—C14	107.02 (11)	N2—C13—C12—C11	0.8 (2)
O4—Co1—O8—C14	−100.60 (11)	C14—C13—C12—C11	−179.66 (13)
O5—Co1—O8—C14	6.25 (17)	N2—C9—C10—C11	1.3 (2)
Co1—O4—C7—O3	−168.85 (12)	C8—C9—C10—C11	−175.84 (14)
Co1—O4—C7—C6	12.83 (16)	Co1—O2—C1—O1	−169.47 (12)
C2—N1—C6—C5	−1.3 (2)	Co1—O2—C1—C2	10.27 (16)
Co1—N1—C6—C5	174.37 (11)	N1—C2—C1—O1	170.25 (13)
C2—N1—C6—C7	176.50 (12)	C3—C2—C1—O1	−10.1 (2)
Co1—N1—C6—C7	−7.81 (15)	N1—C2—C1—O2	−9.50 (18)
O3—C7—C6—N1	177.41 (13)	C3—C2—C1—O2	170.14 (14)
O4—C7—C6—N1	−4.14 (18)	N1—C2—C3—C4	1.6 (2)
O3—C7—C6—C5	−4.9 (2)	C1—C2—C3—C4	−178.01 (13)
O4—C7—C6—C5	173.53 (14)	C9—C10—C11—C12	−1.2 (2)
C10—C9—N2—C13	−0.4 (2)	C13—C12—C11—C10	0.2 (2)
C8—C9—N2—C13	177.06 (12)	C6—C5—C4—C3	0.5 (2)
C10—C9—N2—Co1	179.80 (11)	C2—C3—C4—C5	−1.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12B···O3i	0.79 (3)	2.06 (3)	2.8428 (18)	174 (3)
O11—H11B···O5	0.83 (3)	2.00 (3)	2.8290 (18)	177 (3)
O11—H11A···O1ii	0.81 (3)	2.02 (3)	2.8173 (19)	170 (3)
O10—H10B···O7	0.79 (3)	2.15 (3)	2.9213 (19)	165 (3)
O10—H10A···O11iii	0.87 (3)	1.99 (3)	2.854 (2)	172 (3)
O9—H9B···O8	0.79 (3)	1.96 (3)	2.7521 (18)	175 (2)
O9—H9A···O12iv	0.83 (3)	2.01 (3)	2.840 (2)	173 (3)
N4—H4B···O3v	0.89 (2)	1.92 (2)	2.7973 (18)	165 (2)
N4—H4A···O6iii	0.91 (2)	1.89 (2)	2.7592 (17)	161 (2)
N3—H3B···O9vi	0.91 (2)	1.86 (2)	2.6958 (18)	152 (2)
N3—H3A···O2	0.91 (2)	2.50 (2)	3.1126 (19)	124.5 (18)
N3—H3A···O1	0.91 (2)	1.88 (2)	2.7957 (18)	176 (2)
C18—H18B···O10vii	0.97	2.58	3.457 (2)	151.
C17—H17B···O7vii	0.97	2.36	3.127 (2)	135.
C16—H16B···O12iv	0.97	2.52	3.293 (2)	137.
C15—H15B···O10vi	0.97	2.60	3.261 (2)	126.
C15—H15A···O2	0.97	2.54	3.140 (2)	120.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O12—H12B⋯O3i	0.79 (3)	2.06 (3)	2.8428 (18)	174 (3)
O11—H11B⋯O5	0.83 (3)	2.00 (3)	2.8290 (18)	177 (3)
O11—H11A⋯O1ii	0.81 (3)	2.02 (3)	2.8173 (19)	170 (3)
O10—H10B⋯O7	0.79 (3)	2.15 (3)	2.9213 (19)	165 (3)
O10—H10A⋯O11iii	0.87 (3)	1.99 (3)	2.854 (2)	172 (3)
O9—H9B⋯O8	0.79 (3)	1.96 (3)	2.7521 (18)	175 (2)
O9—H9A⋯O12iv	0.83 (3)	2.01 (3)	2.840 (2)	173 (3)
N4—H4B⋯O3v	0.89 (2)	1.92 (2)	2.7973 (18)	165 (2)
N4—H4A⋯O6iii	0.91 (2)	1.89 (2)	2.7592 (17)	161 (2)
N3—H3B⋯O9vi	0.91 (2)	1.86 (2)	2.6958 (18)	152 (2)
N3—H3A⋯O2	0.91 (2)	2.50 (2)	3.1126 (19)	124.5 (18)
N3—H3A⋯O1	0.91 (2)	1.88 (2)	2.7957 (18)	176 (2)
C18—H18B⋯O10vii	0.97	2.58	3.457 (2)	151
C17—H17B⋯O7vii	0.97	2.36	3.127 (2)	135
C16—H16B⋯O12iv	0.97	2.52	3.293 (2)	137
C15—H15B⋯O10vi	0.97	2.60	3.261 (2)	126
C15—H15A⋯O2	0.97	2.54	3.140 (2)	120

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