Tris(1H-imidazole-κN)(7-oxabicyclo-[2.2.1]heptane-2,3-dicarboxyl-ato-κO,O,O)cobalt(II) 3.35-hydrate.

In the crystal structure of the title compound, [Co(C(8)H(8)O(5))(C(3)H(4)N(2))(3)]·3.35H(2)O, the central Co(II) ion is in a slightly distorted octa-hedral environment, coordinated by the bridg-ing O atom from the bicyclo-[2.2.1]heptane ligand, by two carboxyl-ate O atoms from two different carboxyl-ate groups and by three N atoms from imidazole ligands. Uncoordinated water mol-ecules, some of them disordered, are present in the crystal structure. In the crystal structure, mol-ecules are linked by O-H⋯O, N-H⋯O and O-H⋯N hydrogen-bonding inter-actions.

Related literature

For several cobalt complexes of norcantharidin, see: Wang et al. (1988 ▶) and of imidazole, see: Furenlid et al. (1986 ▶); Zhu et al. (2003 ▶).

Experimental

Crystal data

[Co(C8H8O5)(C3H4N2)3]·3.35H2O

M = 507.67

Triclinic,

a = 8.2666 (2) Å

b = 12.6522 (5) Å

c = 12.7200 (3) Å

α = 109.912 (2)°

β = 104.394 (1)°

γ = 95.354 (2)°

V = 1188.23 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.78 mm−1

T = 296 K

0.41 × 0.36 × 0.29 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.735, T max = 0.798

18153 measured reflections

5402 independent reflections

4712 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.241

S = 1.11

5402 reflections

307 parameters

H-atom parameters constrained

Δρmax = 1.54 e Å−3

Δρmin = −0.74 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024039/at2795sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024039/at2795Isup2.hkl

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

[Co(C8H8O5)(C3H4N2)3]·3.35H2O	Z = 2
Mr = 507.67	F(000) = 529
Triclinic, P1	Dx = 1.419 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2666 (2) Å	Cell parameters from 8576 reflections
b = 12.6522 (5) Å	θ = 1.8–27.7°
c = 12.7200 (3) Å	µ = 0.78 mm−1
α = 109.912 (2)°	T = 296 K
β = 104.394 (1)°	Block, orange
γ = 95.354 (2)°	0.41 × 0.36 × 0.29 mm
V = 1188.23 (6) Å3

Bruker APEXII area-detector diffractometer	5402 independent reflections
Radiation source: fine-focus sealed tube	4712 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω scans	θmax = 27.7°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.735, Tmax = 0.798	k = −15→16
18153 measured reflections	l = −16→16

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.241	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.1424P)2 + 2.537P] where P = (Fo2 + 2Fc2)/3
5402 reflections	(Δ/σ)max = 0.001
307 parameters	Δρmax = 1.54 e Å−3
0 restraints	Δρmin = −0.74 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	Occ. (<1)
Co1	0.63081 (6)	0.68205 (4)	0.83619 (4)	0.0284 (2)
N1	0.7319 (4)	0.7409 (3)	1.0204 (3)	0.0341 (7)
N2	0.6963 (5)	0.5190 (3)	0.8077 (3)	0.0346 (7)
N3	0.3830 (4)	0.6199 (3)	0.8333 (3)	0.0349 (7)
N4	0.9131 (7)	0.8220 (5)	1.2013 (5)	0.0693 (14)
H4C	1.0039	0.8564	1.2590	0.083*
N5	0.6939 (6)	0.3370 (3)	0.7193 (5)	0.0574 (12)
H5B	0.6793	0.2715	0.6638	0.069*
N6	0.1391 (6)	0.5038 (5)	0.7969 (5)	0.0643 (13)
H6B	0.0643	0.4437	0.7798	0.077*
O1	0.8683 (4)	0.7508 (3)	0.8304 (3)	0.0391 (7)
O1W	0.7281 (7)	0.8341 (4)	0.4258 (4)	0.0742 (13)
H1WA	0.7302	0.9031	0.4678	0.089*
H1WB	0.6385	0.7925	0.4222	0.089*
O2W	0.3268 (4)	0.9162 (3)	0.4450 (2)	0.0376 (7)
H2WA	0.2966	0.8498	0.4443	0.045*
H2WB	0.4062	0.9147	0.4132	0.045*
O2	0.5497 (5)	0.6445 (3)	0.6545 (3)	0.0451 (8)
O3	1.0444 (5)	0.8533 (4)	0.7804 (5)	0.0725 (14)
O3W	1.091 (2)	0.5698 (11)	0.5348 (6)	0.191 (9)	0.62
H3WA	1.1554	0.5213	0.5352	0.229*	0.62
H3WB	1.1423	0.6254	0.5251	0.229*	0.62
O3W'	0.9060 (13)	0.5536 (8)	0.5087 (6)	0.044 (2)	0.38
H4WA	0.8377	0.5995	0.5196	0.052*	0.38
H4WB	0.8626	0.4913	0.5114	0.052*	0.38
O4W	1.0657 (12)	0.8869 (16)	0.5732 (9)	0.091 (6)	0.35
H5WA	1.0732	0.9208	0.6450	0.110*	0.35
H5WB	1.0588	0.8156	0.5590	0.110*	0.35
O4	0.6568 (6)	0.6890 (3)	0.5285 (3)	0.0546 (9)
O5	0.5636 (4)	0.8523 (2)	0.8560 (2)	0.0317 (6)
C1	0.7756 (5)	0.9070 (3)	0.7836 (4)	0.0356 (8)
H1A	0.8265	0.9744	0.7730	0.043*
C2	0.7068 (5)	0.9451 (3)	0.8892 (4)	0.0362 (9)
H2A	0.7914	0.9584	0.9640	0.043*
C3	0.6172 (7)	1.0455 (4)	0.8901 (5)	0.0495 (12)
H3A	0.6853	1.1039	0.8772	0.059*
H3B	0.5916	1.0798	0.9634	0.059*
C4	0.4520 (7)	0.9865 (4)	0.7860 (5)	0.0472 (11)
H4A	0.3510	0.9953	0.8114	0.057*
H4B	0.4464	1.0163	0.7246	0.057*
C5	0.4739 (5)	0.8612 (3)	0.7458 (4)	0.0343 (8)
H5A	0.3661	0.8060	0.7038	0.041*
C6	0.6067 (5)	0.8427 (3)	0.6801 (4)	0.0342 (8)
H6A	0.5887	0.8810	0.6241	0.041*
C7	0.9075 (5)	0.8317 (4)	0.7984 (4)	0.0385 (9)
C8	0.6040 (6)	0.7161 (4)	0.6169 (4)	0.0371 (9)
C9	0.3052 (6)	0.5083 (4)	0.8036 (5)	0.0453 (11)
H9A	0.3589	0.4457	0.7901	0.054*
C10	0.1132 (5)	0.6143 (4)	0.8230 (4)	0.0339 (8)
H10A	0.0110	0.6385	0.8261	0.041*
C11	0.2615 (5)	0.6804 (4)	0.8431 (4)	0.0380 (9)
H11A	0.2776	0.7591	0.8617	0.046*
C12	0.6597 (6)	0.4343 (4)	0.7060 (5)	0.0455 (10)
H12A	0.6159	0.4406	0.6341	0.055*
C13	0.7553 (8)	0.3606 (5)	0.8352 (6)	0.0592 (15)
H13A	0.7900	0.3096	0.8703	0.071*
C14	0.7564 (7)	0.4729 (4)	0.8902 (5)	0.0479 (11)
H14A	0.7921	0.5128	0.9709	0.057*
C15	0.8950 (6)	0.7955 (5)	1.0852 (4)	0.0519 (12)
H15A	0.9810	0.8122	1.0548	0.062*
C16	0.7597 (6)	0.7835 (4)	1.2069 (3)	0.0349 (8)
H16A	0.7321	0.7890	1.2749	0.042*
C17	0.6539 (6)	0.7360 (4)	1.0978 (4)	0.0404 (9)
H17A	0.5397	0.7035	1.0787	0.048*

	U11	U22	U33	U12	U13	U23
Co1	0.0262 (3)	0.0286 (3)	0.0308 (3)	0.0069 (2)	0.0089 (2)	0.0113 (2)
N1	0.0325 (17)	0.0372 (17)	0.0323 (17)	0.0075 (14)	0.0079 (14)	0.0141 (14)
N2	0.0330 (17)	0.0310 (16)	0.0418 (18)	0.0094 (13)	0.0126 (14)	0.0142 (14)
N3	0.0270 (16)	0.0350 (17)	0.0418 (18)	0.0065 (13)	0.0086 (14)	0.0148 (15)
N4	0.070 (3)	0.075 (3)	0.048 (3)	0.001 (3)	0.001 (2)	0.019 (2)
N5	0.059 (3)	0.0284 (19)	0.078 (3)	0.0115 (18)	0.023 (2)	0.009 (2)
N6	0.046 (2)	0.061 (3)	0.086 (4)	0.000 (2)	0.021 (2)	0.030 (3)
O1	0.0350 (15)	0.0425 (16)	0.0522 (18)	0.0137 (13)	0.0216 (14)	0.0251 (14)
O1W	0.099 (4)	0.078 (3)	0.060 (3)	0.020 (3)	0.043 (3)	0.029 (2)
O2W	0.0422 (16)	0.0350 (14)	0.0265 (13)	0.0221 (13)	0.0029 (12)	0.0021 (11)
O2	0.066 (2)	0.0317 (15)	0.0354 (16)	0.0101 (14)	0.0132 (15)	0.0111 (12)
O3	0.040 (2)	0.081 (3)	0.134 (4)	0.0207 (19)	0.043 (2)	0.071 (3)
O3W	0.271 (17)	0.180 (11)	0.027 (3)	−0.178 (12)	−0.009 (6)	0.020 (5)
O3W'	0.069 (6)	0.063 (5)	0.022 (3)	0.060 (5)	0.029 (4)	0.021 (3)
O4W	0.027 (5)	0.205 (17)	0.031 (5)	−0.031 (7)	−0.004 (4)	0.054 (8)
O4	0.080 (3)	0.050 (2)	0.0413 (18)	0.0216 (18)	0.0306 (18)	0.0152 (15)
O5	0.0320 (14)	0.0287 (13)	0.0330 (14)	0.0067 (11)	0.0086 (11)	0.0103 (11)
C1	0.037 (2)	0.0283 (18)	0.044 (2)	0.0063 (15)	0.0145 (17)	0.0140 (16)
C2	0.035 (2)	0.0288 (18)	0.038 (2)	0.0029 (15)	0.0080 (17)	0.0069 (16)
C3	0.057 (3)	0.027 (2)	0.059 (3)	0.0092 (19)	0.019 (2)	0.0073 (19)
C4	0.052 (3)	0.040 (2)	0.055 (3)	0.024 (2)	0.018 (2)	0.019 (2)
C5	0.034 (2)	0.0325 (19)	0.035 (2)	0.0105 (15)	0.0073 (16)	0.0122 (16)
C6	0.041 (2)	0.0323 (19)	0.0319 (19)	0.0131 (16)	0.0100 (16)	0.0139 (16)
C7	0.032 (2)	0.038 (2)	0.046 (2)	0.0063 (16)	0.0137 (18)	0.0167 (18)
C8	0.044 (2)	0.037 (2)	0.0276 (18)	0.0141 (17)	0.0061 (16)	0.0104 (16)
C9	0.038 (2)	0.038 (2)	0.067 (3)	0.0092 (18)	0.022 (2)	0.024 (2)
C10	0.0213 (16)	0.040 (2)	0.040 (2)	0.0085 (15)	0.0111 (15)	0.0134 (17)
C11	0.033 (2)	0.039 (2)	0.041 (2)	0.0093 (17)	0.0128 (17)	0.0109 (17)
C12	0.046 (3)	0.037 (2)	0.049 (3)	0.0099 (19)	0.014 (2)	0.0108 (19)
C13	0.069 (4)	0.046 (3)	0.086 (4)	0.026 (3)	0.036 (3)	0.041 (3)
C14	0.054 (3)	0.049 (3)	0.055 (3)	0.022 (2)	0.022 (2)	0.030 (2)
C15	0.036 (2)	0.071 (3)	0.041 (2)	−0.004 (2)	0.0040 (19)	0.021 (2)
C16	0.047 (2)	0.035 (2)	0.0255 (17)	0.0134 (17)	0.0125 (16)	0.0135 (15)
C17	0.043 (2)	0.041 (2)	0.041 (2)	0.0109 (18)	0.0162 (19)	0.0179 (19)

Co1—O1	2.101 (3)	O4W—H5WB	0.8502
Co1—O2	2.107 (3)	O4—C8	1.258 (5)
Co1—N3	2.112 (3)	O5—C2	1.453 (5)
Co1—N1	2.113 (3)	O5—C5	1.461 (5)
Co1—N2	2.116 (3)	C1—C7	1.531 (6)
Co1—O5	2.222 (3)	C1—C2	1.534 (6)
N1—C17	1.319 (6)	C1—C6	1.578 (6)
N1—C15	1.364 (6)	C1—H1A	0.9800
N2—C12	1.310 (6)	C2—C3	1.528 (6)
N2—C14	1.378 (6)	C2—H2A	0.9800
N3—C11	1.323 (5)	C3—C4	1.553 (8)
N3—C9	1.377 (6)	C3—H3A	0.9700
N4—C16	1.343 (7)	C3—H3B	0.9700
N4—C15	1.363 (7)	C4—C5	1.534 (6)
N4—H4C	0.8600	C4—H4A	0.9700
N5—C12	1.344 (7)	C4—H4B	0.9700
N5—C13	1.350 (8)	C5—C6	1.526 (6)
N5—H5B	0.8600	C5—H5A	0.9800
N6—C9	1.349 (7)	C6—C8	1.523 (6)
N6—C10	1.374 (7)	C6—H6A	0.9800
N6—H6B	0.8600	C9—H9A	0.9300
O1—C7	1.268 (5)	C10—C11	1.333 (6)
O1W—H1WA	0.8501	C10—H10A	0.9300
O1W—H1WB	0.8499	C11—H11A	0.9300
O2W—H2WA	0.8500	C12—H12A	0.9300
O2W—H2WB	0.8503	C13—C14	1.351 (7)
O2—C8	1.257 (6)	C13—H13A	0.9300
O3—C7	1.234 (6)	C14—H14A	0.9300
O3W—H3WA	0.8500	C15—H15A	0.9300
O3W—H3WB	0.8498	C16—C17	1.336 (6)
O3W'—H4WA	0.8499	C16—H16A	0.9300
O3W'—H4WB	0.8502	C17—H17A	0.9300
O4W—H5WA	0.8500
O1—Co1—O2	85.20 (14)	C2—C3—H3A	111.4
O1—Co1—N3	175.35 (12)	C4—C3—H3A	111.4
O2—Co1—N3	91.49 (15)	C2—C3—H3B	111.4
O1—Co1—N1	88.60 (14)	C4—C3—H3B	111.4
O2—Co1—N1	172.12 (13)	H3A—C3—H3B	109.2
N3—Co1—N1	94.41 (14)	C5—C4—C3	101.3 (4)
O1—Co1—N2	91.64 (13)	C5—C4—H4A	111.5
O2—Co1—N2	91.04 (13)	C3—C4—H4A	111.5
N3—Co1—N2	91.68 (14)	C5—C4—H4B	111.5
N1—Co1—N2	93.99 (14)	C3—C4—H4B	111.5
O1—Co1—O5	86.79 (11)	H4A—C4—H4B	109.3
O2—Co1—O5	85.90 (11)	O5—C5—C6	101.7 (3)
N3—Co1—O5	89.72 (12)	O5—C5—C4	102.2 (3)
N1—Co1—O5	88.91 (12)	C6—C5—C4	111.2 (4)
N2—Co1—O5	176.67 (12)	O5—C5—H5A	113.5
C17—N1—C15	104.9 (4)	C6—C5—H5A	113.5
C17—N1—Co1	128.7 (3)	C4—C5—H5A	113.5
C15—N1—Co1	126.4 (3)	C8—C6—C5	112.3 (4)
C12—N2—C14	105.6 (4)	C8—C6—C1	113.4 (3)
C12—N2—Co1	125.7 (3)	C5—C6—C1	101.0 (3)
C14—N2—Co1	127.8 (3)	C8—C6—H6A	110.0
C11—N3—C9	105.4 (4)	C5—C6—H6A	110.0
C11—N3—Co1	125.4 (3)	C1—C6—H6A	110.0
C9—N3—Co1	128.4 (3)	O3—C7—O1	124.0 (4)
C16—N4—C15	105.8 (5)	O3—C7—C1	119.2 (4)
C16—N4—H4C	127.1	O1—C7—C1	116.9 (4)
C15—N4—H4C	127.1	O2—C8—O4	123.3 (4)
C12—N5—C13	107.7 (4)	O2—C8—C6	119.2 (4)
C12—N5—H5B	126.2	O4—C8—C6	117.4 (4)
C13—N5—H5B	126.2	N6—C9—N3	109.5 (4)
C9—N6—C10	106.3 (4)	N6—C9—H9A	125.2
C9—N6—H6B	126.9	N3—C9—H9A	125.2
C10—N6—H6B	126.9	C11—C10—N6	107.3 (4)
C7—O1—Co1	129.5 (3)	C11—C10—H10A	126.3
H1WA—O1W—H1WB	108.4	N6—C10—H10A	126.3
H2WA—O2W—H2WB	108.8	N3—C11—C10	111.4 (4)
C8—O2—Co1	118.5 (3)	N3—C11—H11A	124.3
H3WA—O3W—H3WB	108.3	C10—C11—H11A	124.3
H4WA—O3W'—H4WB	108.1	N2—C12—N5	111.1 (5)
H5WA—O4W—H5WB	108.2	N2—C12—H12A	124.5
C2—O5—C5	96.4 (3)	N5—C12—H12A	124.5
C2—O5—Co1	115.2 (2)	N5—C13—C14	106.5 (5)
C5—O5—Co1	114.1 (2)	N5—C13—H13A	126.8
C7—C1—C2	111.4 (4)	C14—C13—H13A	126.8
C7—C1—C6	114.2 (3)	C13—C14—N2	109.2 (5)
C2—C1—C6	101.4 (3)	C13—C14—H14A	125.4
C7—C1—H1A	109.9	N2—C14—H14A	125.4
C2—C1—H1A	109.9	N4—C15—N1	109.9 (5)
C6—C1—H1A	109.9	N4—C15—H15A	125.1
O5—C2—C3	101.6 (3)	N1—C15—H15A	125.1
O5—C2—C1	102.2 (3)	C17—C16—N4	108.0 (4)
C3—C2—C1	110.4 (4)	C17—C16—H16A	126.0
O5—C2—H2A	113.8	N4—C16—H16A	126.0
C3—C2—H2A	113.8	N1—C17—C16	111.4 (4)
C1—C2—H2A	113.8	N1—C17—H17A	124.3
C2—C3—C4	102.0 (3)	C16—C17—H17A	124.3
O1—Co1—N1—C17	176.2 (4)	C1—C2—C3—C4	71.7 (5)
N3—Co1—N1—C17	−0.2 (4)	C2—C3—C4—C5	1.5 (5)
N2—Co1—N1—C17	−92.2 (4)	C2—O5—C5—C6	58.6 (3)
O5—Co1—N1—C17	89.4 (4)	Co1—O5—C5—C6	−62.7 (3)
O1—Co1—N1—C15	−2.2 (4)	C2—O5—C5—C4	−56.5 (4)
N3—Co1—N1—C15	−178.6 (4)	Co1—O5—C5—C4	−177.8 (3)
N2—Co1—N1—C15	89.4 (4)	C3—C4—C5—O5	33.4 (5)
O5—Co1—N1—C15	−89.0 (4)	C3—C4—C5—C6	−74.5 (5)
O1—Co1—N2—C12	−94.7 (4)	O5—C5—C6—C8	84.1 (4)
O2—Co1—N2—C12	−9.4 (4)	C4—C5—C6—C8	−167.7 (4)
N3—Co1—N2—C12	82.1 (4)	O5—C5—C6—C1	−37.0 (4)
N1—Co1—N2—C12	176.6 (4)	C4—C5—C6—C1	71.2 (4)
O1—Co1—N2—C14	98.0 (4)	C7—C1—C6—C8	2.1 (5)
O2—Co1—N2—C14	−176.7 (4)	C2—C1—C6—C8	−117.8 (4)
N3—Co1—N2—C14	−85.2 (4)	C7—C1—C6—C5	122.4 (4)
N1—Co1—N2—C14	9.3 (4)	C2—C1—C6—C5	2.4 (4)
O2—Co1—N3—C11	−86.7 (4)	Co1—O1—C7—O3	−167.8 (4)
N1—Co1—N3—C11	88.1 (4)	Co1—O1—C7—C1	13.2 (6)
N2—Co1—N3—C11	−177.7 (4)	C2—C1—C7—O3	−131.4 (5)
O5—Co1—N3—C11	−0.8 (4)	C6—C1—C7—O3	114.4 (5)
O2—Co1—N3—C9	82.4 (4)	C2—C1—C7—O1	47.7 (5)
N1—Co1—N3—C9	−102.9 (4)	C6—C1—C7—O1	−66.4 (5)
N2—Co1—N3—C9	−8.7 (4)	Co1—O2—C8—O4	135.3 (4)
O5—Co1—N3—C9	168.3 (4)	Co1—O2—C8—C6	−44.8 (5)
O2—Co1—O1—C7	59.9 (4)	C5—C6—C8—O2	−25.7 (5)
N1—Co1—O1—C7	−115.3 (4)	C1—C6—C8—O2	88.0 (5)
N2—Co1—O1—C7	150.8 (4)	C5—C6—C8—O4	154.1 (4)
O5—Co1—O1—C7	−26.3 (4)	C1—C6—C8—O4	−92.2 (5)
O1—Co1—O2—C8	−38.7 (3)	C10—N6—C9—N3	0.0 (6)
N3—Co1—O2—C8	138.0 (4)	C11—N3—C9—N6	−0.5 (6)
N2—Co1—O2—C8	−130.3 (3)	Co1—N3—C9—N6	−171.2 (4)
O5—Co1—O2—C8	48.4 (3)	C9—N6—C10—C11	0.5 (6)
O1—Co1—O5—C2	−16.1 (3)	C9—N3—C11—C10	0.8 (5)
O2—Co1—O5—C2	−101.6 (3)	Co1—N3—C11—C10	171.9 (3)
N3—Co1—O5—C2	166.9 (3)	N6—C10—C11—N3	−0.9 (6)
N1—Co1—O5—C2	72.5 (3)	C14—N2—C12—N5	−0.2 (6)
O1—Co1—O5—C5	94.0 (3)	Co1—N2—C12—N5	−169.8 (3)
O2—Co1—O5—C5	8.6 (3)	C13—N5—C12—N2	0.0 (6)
N3—Co1—O5—C5	−82.9 (3)	C12—N5—C13—C14	0.2 (6)
N1—Co1—O5—C5	−177.3 (3)	N5—C13—C14—N2	−0.3 (6)
C5—O5—C2—C3	57.3 (4)	C12—N2—C14—C13	0.4 (6)
Co1—O5—C2—C3	177.8 (3)	Co1—N2—C14—C13	169.7 (4)
C5—O5—C2—C1	−56.8 (3)	C16—N4—C15—N1	−0.2 (7)
Co1—O5—C2—C1	63.7 (3)	C17—N1—C15—N4	0.4 (6)
C7—C1—C2—O5	−88.8 (4)	Co1—N1—C15—N4	179.2 (4)
C6—C1—C2—O5	33.1 (4)	C15—N4—C16—C17	−0.2 (6)
C7—C1—C2—C3	163.7 (4)	C15—N1—C17—C16	−0.6 (5)
C6—C1—C2—C3	−74.4 (4)	Co1—N1—C17—C16	−179.2 (3)
O5—C2—C3—C4	−36.2 (5)	N4—C16—C17—N1	0.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2Wi	0.85	2.33	3.161 (6)	167
O2W—H2WA···N5ii	0.85	2.59	3.133 (5)	123
O2W—H2WB···O2Wi	0.85	2.69	3.084 (7)	110
O1W—H1WB···O4	0.85	2.17	2.690 (6)	119
N5—H5B···O2Wii	0.86	2.29	3.133 (5)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O2Wi	0.85	2.33	3.161 (6)	167
O2W—H2WA⋯N5ii	0.85	2.59	3.133 (5)	123
O2W—H2WB⋯O2Wi	0.85	2.69	3.084 (7)	110
O1W—H1WB⋯O4	0.85	2.17	2.690 (6)	119
N5—H5B⋯O2Wii	0.86	2.29	3.133 (5)	165

Symmetry codes: (i) ; (ii) .