Triaqua­(cyclo­hex-4-ene-1,2-dicarboxyl­ato-κO¹)(1,10-phenanthroline-κ²N,N′)cobalt(II)

In the title compound, [Co(C₈H₈O₄)(C₁₂H₈N₂)(H₂O)₃], the Co^II atom is coordinated by two N atoms from a bidentate 1,10-phenanthroline ligand, one O atom from a monodentate 4-cyclo­hexene-1,2-dicarboxyl­ate ligand and three water O atoms in a distorted octa­hedral geometry. The mononuclear mol­ecules are engaged in extensive intra- and inter­molecular O—H...O hydrogen-bonding inter­actions and π–π stacking inter­actions [centroid–centroid distance = 3.784 (3) Å], forming a three-dimensional supra­molecular network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.061
• wR factor = 0.122
• Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0061 Ang
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     17.054
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      3.128
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          5

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          9
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         69
            O1  -CO1 -N2  -C19    69.00  3.00   1.555   1.555   1.555   1.555
PLAT793_ALERT_4_G The Model has Chirality at C2      (Verify) ....          S
PLAT793_ALERT_4_G The Model has Chirality at C7      (Verify) ....          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          9
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          61 Perc.

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

Recently, carboxylic acid (as well as carboxylate) has been widely applied in engineering studies of inorganic-organic hybrid materials and the construction of metal-organic coordination supramolecular complexes (Huang et al., 2010; Ockwig et al., 2005; Rao et al., 2004). Although the Cambridge Structural Database (Allen, 2002) contains a great number of transition metal derivatives of carboxylic acids, the metal derivatives of cis-4-cyclohexene-1,2-dicarboxylate acid documented are surprisingly rare (Kim et al., 2004; Lee et al., 2006). As part of this ongoing work, the title complex, [Co(C₈H₈O₄)(C₁₂H₈N₂)(H₂O)₃], has been prepared and structurally characterized (Fig. 1).

In the title compound, the Co^II atom is coordinated by two N atoms from a bidentate 1,10-phenanthroline ligand (phen), one O atom from a monodentate cis-4-cyclohexene-1,2-dicarboxylate ligand, and three O atoms from water molecules in a distorted octahedral geometry. The coordinating Co—N and Co—O bond lengths [Co—N 2.107 (3)–2.122 (3) Å; Co—O 2.071 (3)–2.152 (3) Å] agree well with those observed in analogous complexes (Baruah et al., 2007; Hou et al., 2007; Zhang et al., 2008). The crystal packing (Fig. 2) exhibits intra- and inter-molecular O—H···O hydrogen bonds (Table 1) and π–π stacking interactions [Cg1···Cg2ⁱⁱⁱ distance is 3.784 (3) Å (iii = -x, 1-y, 1-z) between the centroids of the (N1-C9-C10-C11-C12-C20) and (C12-C13-C14-C15-C19-C20) six-membered rings] forming a three-dimensional supramolecular network.

Related literature

For background to compounds with metal-organic framework structures, see: Huang et al. (2010); Ockwig et al. (2005); Rao et al. (2004). For a description of the Cambridge Structural Database (CSD), see: Allen (2002). For 4-cyclohexene-1,2-dicarboxylates, see: Kim et al. (2004); Lee et al. (2006). For related structures, see: Baruah et al. (2007); Hou et al. (2007); Zhang et al. (2008).

S2. Experimental

For the preparation of the title complex, cis-4-cyclohexene-1,2-dicarboxylate acid (0.085 g, 0.5 mmol), Co(NO₃)₂.6H₂O (0.12 g, 0.5 mmol), phen (0.10 g, 0.5 mmol) and KHCO₃ (0.10 g, 1 mmol) were dissolved in a water/ethanol solution (20 ml, 1:1). The solution was stirred for 3 h at room temperature and filtered. Red block-shaped crystals were obtained from the filtrate after 4 d.

S3. Refinement

H atoms of water molecules were located in a difference Fourier map and refined with distance restraints of O—H = 0.85 (2) Å and H···H = 1.39 (2) Å. All other H atoms were positoned geometrically and refined using a riding model, with C—H = 0.93 Å for C—H_aromatic and C—H = 0.97 Å for C—H_aliphatic [U_iso(H) = 1.2U_eq(C)] .

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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: SHELXTL (Sheldrick, 2008).

Figures

	Fig. 1. The asymmetric unit of the title compound with the atom-numbering scheme and displacement ellipsoids at the 30% probability level.
	Fig. 2. A packing diagram of the title compound. Hydrogen bonds are shown as dotted lines.

Triaqua(cyclohex-4-ene-1,2-dicarboxylato-κO¹)(1,10-phenanthroline- κ²N,N')cobalt(II)

Crystal data

[Co(C8H8O4)(C12H8N2)(H2O)3]	F(000) = 956
Mr = 461.33	Dx = 1.538 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2567 reflections
a = 8.1730 (16) Å	θ = 1.5–25.3°
b = 20.210 (4) Å	µ = 0.91 mm^−1
c = 12.068 (2) Å	T = 293 K
β = 91.44 (3)°	Block, red
V = 1992.7 (7) Å^3	0.40 × 0.20 × 0.08 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	3606 independent reflections
Radiation source: fine-focus sealed tube	2982 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.073
phi and ω scans	θmax = 25.3°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.801, Tmax = 0.945	k = −24→24
15996 measured reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0338P)^2 + 5.P] where P = (Fo^2 + 2Fc^2)/3
3606 reflections	(Δ/σ)max < 0.001
295 parameters	Δρmax = 0.28 e Å^−3
9 restraints	Δρmin = −0.34 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Co1	0.23393 (6)	0.53534 (3)	0.19466 (4)	0.02844 (17)
C1	0.3182 (5)	0.67605 (19)	0.1389 (3)	0.0319 (9)
C2	0.4497 (5)	0.71600 (19)	0.0814 (3)	0.0327 (9)
H2A	0.4249	0.7143	0.0016	0.039*
C3	0.4475 (6)	0.7890 (2)	0.1160 (4)	0.0463 (12)
H3A	0.5051	0.8151	0.0620	0.056*
H3B	0.3352	0.8045	0.1169	0.056*
C4	0.5250 (6)	0.7988 (2)	0.2267 (5)	0.0567 (14)
H4A	0.5006	0.8372	0.2655	0.068*
C5	0.6267 (6)	0.7561 (3)	0.2732 (4)	0.0545 (14)
H5C	0.6676	0.7657	0.3440	0.065*
C6	0.6815 (5)	0.6932 (2)	0.2206 (4)	0.0400 (11)
H6C	0.6419	0.6560	0.2632	0.048*
H6D	0.8001	0.6916	0.2228	0.048*
C7	0.6202 (5)	0.68620 (19)	0.1002 (3)	0.0319 (9)
H7C	0.6947	0.7123	0.0553	0.038*
C8	0.6262 (5)	0.61588 (19)	0.0556 (3)	0.0305 (9)
C9	0.3023 (5)	0.5544 (2)	0.4478 (3)	0.0387 (10)
H9A	0.3474	0.5952	0.4298	0.046*
C10	0.3035 (6)	0.5346 (2)	0.5592 (4)	0.0460 (12)
H10A	0.3491	0.5619	0.6138	0.055*
C11	0.2385 (6)	0.4760 (2)	0.5869 (4)	0.0446 (12)
H11A	0.2392	0.4628	0.6608	0.054*
C12	0.1695 (5)	0.4345 (2)	0.5047 (3)	0.0369 (10)
C13	0.0959 (6)	0.3723 (2)	0.5252 (4)	0.0446 (11)
H13A	0.0915	0.3568	0.5976	0.054*
C14	0.0322 (6)	0.3351 (2)	0.4419 (4)	0.0457 (12)
H14A	−0.0140	0.2942	0.4577	0.055*
C15	0.0348 (5)	0.3577 (2)	0.3300 (3)	0.0359 (10)
C16	−0.0345 (5)	0.3215 (2)	0.2400 (4)	0.0426 (11)
H16A	−0.0839	0.2807	0.2518	0.051*
C17	−0.0280 (5)	0.3472 (2)	0.1365 (4)	0.0429 (11)
H17A	−0.0732	0.3242	0.0764	0.051*
C18	0.0467 (5)	0.4080 (2)	0.1210 (3)	0.0357 (10)
H18A	0.0505	0.4246	0.0493	0.043*
C19	0.1057 (5)	0.41830 (19)	0.3069 (3)	0.0295 (9)
C20	0.1743 (5)	0.4581 (2)	0.3947 (3)	0.0306 (9)
N1	0.2392 (4)	0.51715 (16)	0.3679 (3)	0.0312 (8)
N2	0.1127 (4)	0.44351 (16)	0.2022 (3)	0.0295 (8)
O1	0.3622 (3)	0.62360 (13)	0.1889 (2)	0.0315 (6)
O2	0.1735 (3)	0.69566 (14)	0.1286 (3)	0.0439 (8)
O3	0.5410 (3)	0.60345 (14)	−0.0292 (2)	0.0382 (7)
O4	0.7164 (3)	0.57339 (13)	0.1038 (2)	0.0356 (7)
O5	0.4681 (4)	0.48671 (15)	0.1938 (2)	0.0349 (7)
O6	0.2453 (4)	0.53756 (15)	0.0198 (2)	0.0334 (7)
O7	0.0207 (4)	0.59085 (15)	0.1985 (3)	0.0378 (7)
H5A	0.465 (6)	0.4552 (16)	0.147 (3)	0.062 (17)*
H6A	0.258 (5)	0.5009 (13)	−0.015 (4)	0.061 (17)*
H7A	0.054 (5)	0.6283 (14)	0.174 (4)	0.052 (15)*
H5B	0.538 (5)	0.5151 (17)	0.172 (4)	0.059 (17)*
H6B	0.324 (4)	0.5630 (16)	0.000 (4)	0.054 (16)*
H7B	−0.077 (3)	0.584 (2)	0.172 (4)	0.059 (16)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0293 (3)	0.0295 (3)	0.0264 (3)	−0.0004 (2)	0.0010 (2)	0.0015 (2)
C1	0.037 (3)	0.025 (2)	0.033 (2)	0.0006 (18)	0.0004 (18)	−0.0067 (18)
C2	0.039 (2)	0.028 (2)	0.031 (2)	0.0023 (18)	0.0014 (18)	0.0018 (18)
C3	0.044 (3)	0.027 (2)	0.069 (3)	0.001 (2)	0.008 (2)	0.004 (2)
C4	0.053 (3)	0.038 (3)	0.080 (4)	0.002 (2)	0.005 (3)	−0.028 (3)
C5	0.055 (3)	0.058 (3)	0.050 (3)	−0.009 (3)	−0.001 (2)	−0.030 (3)
C6	0.039 (3)	0.040 (3)	0.040 (3)	−0.005 (2)	−0.005 (2)	−0.008 (2)
C7	0.031 (2)	0.031 (2)	0.034 (2)	−0.0034 (18)	0.0025 (18)	0.0011 (18)
C8	0.028 (2)	0.030 (2)	0.034 (2)	−0.0042 (18)	0.0074 (18)	−0.0021 (18)
C9	0.045 (3)	0.038 (2)	0.033 (2)	−0.005 (2)	0.000 (2)	−0.0021 (19)
C10	0.059 (3)	0.047 (3)	0.032 (2)	−0.002 (2)	−0.010 (2)	−0.010 (2)
C11	0.057 (3)	0.050 (3)	0.027 (2)	0.002 (2)	−0.003 (2)	0.001 (2)
C12	0.039 (3)	0.042 (3)	0.030 (2)	0.002 (2)	0.0023 (19)	0.0049 (19)
C13	0.054 (3)	0.050 (3)	0.030 (2)	−0.004 (2)	−0.001 (2)	0.011 (2)
C14	0.054 (3)	0.043 (3)	0.040 (3)	−0.009 (2)	0.002 (2)	0.011 (2)
C15	0.035 (2)	0.038 (2)	0.035 (2)	−0.0007 (19)	−0.0006 (19)	0.0013 (19)
C16	0.040 (3)	0.037 (3)	0.051 (3)	−0.011 (2)	−0.001 (2)	0.002 (2)
C17	0.043 (3)	0.049 (3)	0.036 (3)	−0.012 (2)	−0.005 (2)	−0.004 (2)
C18	0.038 (2)	0.043 (3)	0.026 (2)	−0.003 (2)	−0.0022 (18)	−0.0007 (19)
C19	0.027 (2)	0.033 (2)	0.028 (2)	−0.0013 (17)	0.0009 (17)	0.0007 (17)
C20	0.030 (2)	0.035 (2)	0.026 (2)	0.0045 (18)	0.0017 (17)	0.0014 (18)
N1	0.033 (2)	0.0333 (19)	0.0272 (19)	0.0009 (15)	0.0018 (15)	−0.0008 (15)
N2	0.0291 (18)	0.0335 (19)	0.0261 (18)	−0.0026 (15)	0.0024 (14)	−0.0007 (14)
O1	0.0310 (15)	0.0284 (15)	0.0349 (16)	−0.0012 (12)	−0.0008 (12)	0.0018 (12)
O2	0.0292 (17)	0.0342 (17)	0.068 (2)	0.0063 (13)	−0.0034 (15)	0.0008 (15)
O3	0.0409 (17)	0.0386 (17)	0.0349 (17)	0.0004 (13)	−0.0023 (14)	−0.0103 (13)
O4	0.0337 (16)	0.0298 (16)	0.0432 (18)	0.0029 (13)	−0.0031 (13)	−0.0023 (13)
O5	0.0360 (18)	0.0356 (17)	0.0329 (17)	0.0033 (14)	0.0010 (13)	−0.0023 (14)
O6	0.0376 (18)	0.0334 (17)	0.0293 (16)	−0.0010 (14)	0.0023 (12)	−0.0015 (14)
O7	0.0280 (17)	0.0381 (19)	0.0474 (19)	0.0029 (14)	0.0000 (14)	0.0003 (15)

Geometric parameters (Å, º)

Co1—O1	2.071 (3)	C9—H9A	0.9300
Co1—O7	2.074 (3)	C10—C11	1.345 (6)
Co1—N2	2.107 (3)	C10—H10A	0.9300
Co1—O6	2.115 (3)	C11—C12	1.407 (6)
Co1—N1	2.122 (3)	C11—H11A	0.9300
Co1—O5	2.152 (3)	C12—C20	1.412 (5)
C1—O2	1.250 (5)	C12—C13	1.418 (6)
C1—O1	1.268 (5)	C13—C14	1.348 (6)
C1—C2	1.525 (6)	C13—H13A	0.9300
C2—C7	1.530 (6)	C14—C15	1.427 (6)
C2—C3	1.533 (6)	C14—H14A	0.9300
C2—H2A	0.9800	C15—C19	1.387 (6)
C3—C4	1.477 (7)	C15—C16	1.415 (6)
C3—H3A	0.9700	C16—C17	1.355 (6)
C3—H3B	0.9700	C16—H16A	0.9300
C4—C5	1.315 (7)	C17—C18	1.386 (6)
C4—H4A	0.9300	C17—H17A	0.9300
C5—C6	1.494 (6)	C18—N2	1.319 (5)
C5—H5C	0.9300	C18—H18A	0.9300
C6—C7	1.531 (6)	C19—N2	1.364 (5)
C6—H6C	0.9700	C19—C20	1.433 (5)
C6—H6D	0.9700	C20—N1	1.349 (5)
C7—C8	1.521 (5)	O5—H5A	0.852 (19)
C7—H7C	0.9800	O5—H5B	0.854 (19)
C8—O3	1.250 (5)	O6—H6A	0.860 (19)
C8—O4	1.264 (5)	O6—H6B	0.859 (19)
C9—N1	1.319 (5)	O7—H7A	0.859 (18)
C9—C10	1.403 (6)	O7—H7B	0.858 (19)
O1—Co1—O7	87.78 (12)	N1—C9—H9A	119.0
O1—Co1—N2	177.61 (12)	C10—C9—H9A	119.0
O7—Co1—N2	94.53 (13)	C11—C10—C9	119.8 (4)
O1—Co1—O6	85.03 (11)	C11—C10—H10A	120.1
O7—Co1—O6	93.97 (12)	C9—C10—H10A	120.1
N2—Co1—O6	95.43 (12)	C10—C11—C12	120.3 (4)
O1—Co1—N1	100.63 (12)	C10—C11—H11A	119.9
O7—Co1—N1	93.88 (12)	C12—C11—H11A	119.9
N2—Co1—N1	78.61 (12)	C11—C12—C20	116.2 (4)
O6—Co1—N1	170.49 (12)	C11—C12—C13	124.7 (4)
O1—Co1—O5	86.69 (11)	C20—C12—C13	119.0 (4)
O7—Co1—O5	174.34 (13)	C14—C13—C12	121.4 (4)
N2—Co1—O5	90.99 (12)	C14—C13—H13A	119.3
O6—Co1—O5	86.76 (11)	C12—C13—H13A	119.3
N1—Co1—O5	85.96 (12)	C13—C14—C15	120.9 (4)
O2—C1—O1	124.7 (4)	C13—C14—H14A	119.6
O2—C1—C2	117.6 (4)	C15—C14—H14A	119.6
O1—C1—C2	117.7 (4)	C19—C15—C16	117.6 (4)
C1—C2—C7	112.0 (3)	C19—C15—C14	119.3 (4)
C1—C2—C3	111.9 (3)	C16—C15—C14	123.1 (4)
C7—C2—C3	110.8 (3)	C17—C16—C15	119.0 (4)
C1—C2—H2A	107.3	C17—C16—H16A	120.5
C7—C2—H2A	107.3	C15—C16—H16A	120.5
C3—C2—H2A	107.3	C16—C17—C18	119.4 (4)
C4—C3—C2	111.6 (4)	C16—C17—H17A	120.3
C4—C3—H3A	109.3	C18—C17—H17A	120.3
C2—C3—H3A	109.3	N2—C18—C17	123.8 (4)
C4—C3—H3B	109.3	N2—C18—H18A	118.1
C2—C3—H3B	109.3	C17—C18—H18A	118.1
H3A—C3—H3B	108.0	N2—C19—C15	122.9 (4)
C5—C4—C3	123.3 (4)	N2—C19—C20	116.8 (3)
C5—C4—H4A	118.3	C15—C19—C20	120.3 (4)
C3—C4—H4A	118.3	N1—C20—C12	123.0 (4)
C4—C5—C6	124.8 (5)	N1—C20—C19	117.9 (3)
C4—C5—H5C	117.6	C12—C20—C19	119.1 (4)
C6—C5—H5C	117.6	C9—N1—C20	118.6 (3)
C5—C6—C7	112.8 (4)	C9—N1—Co1	128.3 (3)
C5—C6—H6C	109.0	C20—N1—Co1	113.0 (3)
C7—C6—H6C	109.0	C18—N2—C19	117.3 (3)
C5—C6—H6D	109.0	C18—N2—Co1	129.1 (3)
C7—C6—H6D	109.0	C19—N2—Co1	113.6 (2)
H6C—C6—H6D	107.8	C1—O1—Co1	126.8 (2)
C8—C7—C2	110.7 (3)	Co1—O5—H5A	109 (3)
C8—C7—C6	114.2 (3)	Co1—O5—H5B	107 (3)
C2—C7—C6	112.3 (3)	H5A—O5—H5B	108 (3)
C8—C7—H7C	106.4	Co1—O6—H6A	119 (3)
C2—C7—H7C	106.4	Co1—O6—H6B	110 (3)
C6—C7—H7C	106.4	H6A—O6—H6B	107 (3)
O3—C8—O4	123.2 (4)	Co1—O7—H7A	101 (3)
O3—C8—C7	117.1 (4)	Co1—O7—H7B	133 (3)
O4—C8—C7	119.7 (4)	H7A—O7—H7B	108 (3)
N1—C9—C10	122.1 (4)
O2—C1—C2—C7	−179.6 (3)	N2—C19—C20—N1	0.4 (5)
O1—C1—C2—C7	−3.0 (5)	C15—C19—C20—N1	−178.9 (4)
O2—C1—C2—C3	55.3 (5)	N2—C19—C20—C12	179.7 (3)
O1—C1—C2—C3	−128.1 (4)	C15—C19—C20—C12	0.4 (6)
C1—C2—C3—C4	77.6 (5)	C10—C9—N1—C20	−0.1 (6)
C7—C2—C3—C4	−48.1 (5)	C10—C9—N1—Co1	−177.0 (3)
C2—C3—C4—C5	20.1 (7)	C12—C20—N1—C9	0.5 (6)
C3—C4—C5—C6	1.7 (9)	C19—C20—N1—C9	179.7 (4)
C4—C5—C6—C7	5.8 (7)	C12—C20—N1—Co1	177.9 (3)
C1—C2—C7—C8	59.8 (4)	C19—C20—N1—Co1	−2.9 (4)
C3—C2—C7—C8	−174.5 (3)	O1—Co1—N1—C9	2.4 (4)
C1—C2—C7—C6	−69.1 (4)	O7—Co1—N1—C9	−86.0 (4)
C3—C2—C7—C6	56.6 (5)	N2—Co1—N1—C9	−179.9 (4)
C5—C6—C7—C8	−161.8 (4)	O5—Co1—N1—C9	88.3 (4)
C5—C6—C7—C2	−34.8 (5)	O1—Co1—N1—C20	−174.6 (3)
C2—C7—C8—O3	34.0 (5)	O7—Co1—N1—C20	96.9 (3)
C6—C7—C8—O3	161.9 (4)	N2—Co1—N1—C20	3.1 (3)
C2—C7—C8—O4	−146.7 (4)	O5—Co1—N1—C20	−88.7 (3)
C6—C7—C8—O4	−18.9 (5)	C17—C18—N2—C19	−0.1 (6)
N1—C9—C10—C11	−0.2 (7)	C17—C18—N2—Co1	178.9 (3)
C9—C10—C11—C12	0.1 (7)	C15—C19—N2—C18	0.7 (6)
C10—C11—C12—C20	0.3 (7)	C20—C19—N2—C18	−178.6 (4)
C10—C11—C12—C13	−179.0 (5)	C15—C19—N2—Co1	−178.4 (3)
C11—C12—C13—C14	−180.0 (5)	C20—C19—N2—Co1	2.3 (4)
C20—C12—C13—C14	0.7 (7)	O7—Co1—N2—C18	85.1 (4)
C12—C13—C14—C15	−0.8 (7)	O6—Co1—N2—C18	−9.4 (4)
C13—C14—C15—C19	0.7 (7)	N1—Co1—N2—C18	178.1 (4)
C13—C14—C15—C16	−178.1 (4)	O5—Co1—N2—C18	−96.2 (4)
C19—C15—C16—C17	0.4 (6)	O1—Co1—N2—C19	69 (3)
C14—C15—C16—C17	179.2 (4)	O7—Co1—N2—C19	−95.9 (3)
C15—C16—C17—C18	0.2 (7)	O6—Co1—N2—C19	169.6 (3)
C16—C17—C18—N2	−0.4 (7)	N1—Co1—N2—C19	−2.9 (3)
C16—C15—C19—N2	−0.9 (6)	O5—Co1—N2—C19	82.8 (3)
C14—C15—C19—N2	−179.8 (4)	O2—C1—O1—Co1	34.6 (6)
C16—C15—C19—C20	178.4 (4)	C2—C1—O1—Co1	−141.7 (3)
C14—C15—C19—C20	−0.5 (6)	O7—Co1—O1—C1	−36.1 (3)
C11—C12—C20—N1	−0.6 (6)	O6—Co1—O1—C1	58.1 (3)
C13—C12—C20—N1	178.8 (4)	N1—Co1—O1—C1	−129.6 (3)
C11—C12—C20—C19	−179.8 (4)	O5—Co1—O1—C1	145.1 (3)
C13—C12—C20—C19	−0.4 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O3^i	0.85 (3)	1.85 (3)	2.695 (4)	171 (4)
O5—H5B···O4	0.86 (4)	2.06 (4)	2.912 (4)	172 (4)
O6—H6A···O4^i	0.86 (3)	1.86 (4)	2.716 (4)	174 (5)
O6—H6B···O3	0.86 (3)	1.99 (3)	2.835 (4)	165 (3)
O7—H7A···O2	0.86 (3)	1.77 (4)	2.610 (4)	165 (4)
O7—H7B···O4^ii	0.86 (3)	1.87 (3)	2.734 (4)	175 (4)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, y, z.