Poly[[di­aqua­[μ-1,4-bis(pyridin-4-ylmeth­yl)piperazine-κ²N:N′]{μ-2,2′-[(1,4-phenyl­ene)bis(­oxy)]di­acetato-κ²O:O′}cobalt(II)] penta­hydrate]

In the title compound, {[Co(C₁₀H₈O₆)(C₁₆H₂₀N₄)(H₂O)₂]·5H₂O}_n, octa­hedrally coordinated Co^II ions on crystallographic inversion centres are bound by trans O atoms belonging to two hydro­quinone-O,O′-di­acetate (hqda) anions {systematic name: 2,2′-[(1,4-phenyl­ene)bis­(­oxy)]di­acetate}, two trans-pyridine N-donor atoms from two bis­(pyridin-4-ylmeth­yl)piperazine (4-bpmp) ligands, and two trans aqua ligands. The exobidentate hqda and 4-bpmp ligands form [Co(hqda)(4-bpmp)(H₂O)₂]_n coordination polymer layers parallel to (110) that are anchored into the full crystal structure by O—H...O hydrogen bonding between aqua ligands and ligated hqda O atoms. Disordered water mol­ecules of crystallization occupy incipient channels along [100]. However, these could not modeled reliably and so they were treated with SQUEEZE in PLATON [Spek (2009). Acta Cryst. D65, 148–155]; the crystal data take the presence of these mol­ecules into account. The crystal under investigation was twinned by non-merohedry, the twin fraction of the components being 53.3% and 46.7%. Only data from the major twin component were used in the refinement.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.012 Å
Some non-H atoms missing
• R factor = 0.093
• wR factor = 0.228
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level A
CHEMW03_ALERT_2_A ALERT: The ratio of given/expected molecular weight as
            calculated from the _atom_site* data lies outside
            the range 0.90 <> 1.10
           From the CIF: _cell_formula_units_Z                    1
           From the CIF: _chemical_formula_weight           677.57
           TEST: Calculate formula weight from _atom_site_*
           atom     mass    num     sum
           C        12.01   26.00  312.29
           H         1.01   32.00   32.26
           Co       58.93    1.00   58.93
           N        14.01    4.00   56.03
           O        16.00    8.00  127.99
           Calculated formula weight              587.49

Author Response: SQUEEZE was used to model five disordered water molecules in the asymmetric unit.

Alert level C
PLAT041_ALERT_1_C Calc. and Reported SumFormula    Strings  Differ     Please Check
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...     Please Check
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0119 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      4.963 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.223 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          3 Why ?
PLAT975_ALERT_2_C Check Calcd Residual Density  0.83A From      O4       0.47 eA-3

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C26 H42 Co1 N4 O13
            Atom count from the _atom_site data:  C26 H32 Co1 N4 O8
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: Large difference may be due to a
            symmetry error - see SYMMG tests
           From the CIF: _cell_formula_units_Z    1
           From the CIF: _chemical_formula_sum  C26 H42 Co N4 O13
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         26.00     26.00    0.00
           H         42.00     32.00   10.00
           Co         1.00      1.00    0.00
           N          4.00      4.00    0.00
           O         13.00      8.00    5.00
PLAT004_ALERT_5_G Polymeric Structure Found with Dimension .......          2 Info
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Why ?
PLAT044_ALERT_1_G Calculated and Reported Density Dx  Differ by ..     0.1958 Check
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large.       9.30 Why ?
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00200 Degree
PLAT605_ALERT_4_G Structure Contains Solvent Accessible VOIDS of .        158 A   3  
PLAT869_ALERT_4_G ALERTS Related to the use of SQUEEZE Suppressed           ! Info
PLAT910_ALERT_3_G Missing # of FCF Reflections Below Th(Min) .....          1 Why ?
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          5 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check

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

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

---

S1. Chemical context

Some divalent metal terephthalate coordination polymers with bis­(pyridin-4-yl­methyl)­piperazine (4-bpmp) coligands show intriguing entangled topologies. (Farnum et al., 2013). We hoped to expand the scope of these materials by using a para aromatic di­carboxyl­ate with longer pendant arms, such as hydro­quinone-O,O'-di­acetic acid (H₂hqda). The title compound was obtained as pink crystals through the hydro­thermal reaction of cobalt nitrate, H₂hqda, and 4-bpmp.

S2. Structural commentary

The asymmetric unit of the title compound contains a divalent cobalt atom on a crystallographic inversion centre, an aqua ligand, half of a hqda ligand whose centroid rests on another crystallographic inversion centre, and one half of a 4-bpmp ligand whose centroid rests on a third crystallographic inversion centre.

The cobalt atom is o­cta­hedrally coordinated (Fig. 1), with the equatorial plane containing trans pyridyl N atom donors from two 4-bpmp ligands and trans O atom donors from monodentate carboxyl­ate groups belonging to two hqda ligands. The aqua ligands are located in the axial positions.

The Co atoms are connected by exobidentate, bis­(monodentate) hqda ligands to form [Co(hqda)(H₂O)₂]_n coordination polymer chains that are oriented parallel to [0 1 0]. Each individual chain is linked to two others by tethering 4-bpmp ligands, to construct [Co(hqda)(4-bpmp)(H₂O)₂]_n coordination polymer layers parallel to (110) (Fig. 2). As each cobalt atom is connected to four others, the underlying topology of the layer is a (4,4) re­cta­ngular grid. The inter­nuclear Co···Co through-space distances across the grid apertures are 13.17 Å and 25.14 Å.

S3. Supra­molecular features

Individual [Co(hqda)(4-bpmp)(H₂O)₂]_n layers stack in a AAA pattern along the a crystal direction (Fig. 3). The supra­molecular O—H···O hydrogen bonding between aqua ligands in one layer and ligated hqda O atoms in two others provides the impetus for the formation of the three-dimensional crystal structure of the title compound.

Disordered water molecules of crystallization occupy incipient channels along [1 0 0]. These could not be refined well, and thus their electron density was modeled using the SQUEEZE subroutine of PLATON (Spek, 2009). The resulting analysis indicated the presence of approximately five water molecules per unit cell, in a region comprising 20.6% of the total unit cell volume.

S4. Database survey

This compound was not previously reported in the CCDC.

S5. Synthesis and crystallization

Cobalt(II) nitrate hexahydrate and hydro­quinone-O,O'-di­acetic acid (H₂hqda) were obtained commercially. Bis(4-pyridymethyl)­piperazine (4-bpmp) was prepared via a published procedure (Niu et al., 2001). A mixture of cobalt(II) nitrate hexahydrate (68 mg, 0.23 mmol), H₂hqda (84 mg, 0.37 mmol), 4-bpmp (99 mg, 0.37 mmol), 0.25 ml of a 1.0 M NaOH solution and 10.0 g water (550 mmol) was placed into a 23 ml Teflon-lined Parr acid digestion bomb, which was then heated under autogenous pressure at 393 K for 24 h. Pink plates of the title compound were obtained in a multi-phase mixture.

S6. Refinement

All H atoms bound to C atoms were placed in calculated positions, with C—H = 0.95–0.99 Å, and refined in riding mode with U_iso = 1.2U_eq(C). The H atoms within the aqua ligand were found in a difference Fourier map, restrained with O—H = 0.85 Å and refined with U_iso = 1.5U_eq(O).

Related literature

For the preparation of bis(4-pyridymethyl)piperazine, see: Niu et al. (2001). For the preparation of divalent metal terephthalate coordination polymers containing bis(4-pyridymethyl)piperazine, see: Farnum et al. (2013).

Computing details

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures

	Fig. 1. The octahedral coordination environment of the title compound, showing 50% probability ellipsoids and atom numbering scheme. Hydrogen atom positions are shown as gray sticks. Color codes: dark blue Co, red O, light blue N, black C. Symmetry code: (i) -x + 1, -y, -z.
	Fig. 2. A single [Co(hqda)(4-bpmp)(H2O)2]n coordination polymer layer.
	Fig. 3. Stacking of coordination polymer layers within the title compound.

Poly[[diaqua[µ-1,4-bis(pyridin-4-ylmethyl)piperazine-κ²N:N']{µ-2,2'-[(1,4-phenylene)bis(oxy)]diacetato-κ²O:O'}cobalt(II)] pentahydrate]

Crystal data

[Co(C10H8O6)(C16H20N4)(H2O)2]·5H2O	Z = 1
Mr = 677.57	F(000) = 357
Triclinic, P1	Dx = 1.475 Mg m^−3
a = 5.7727 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.3421 (15) Å	Cell parameters from 2300 reflections
c = 13.1675 (19) Å	θ = 2.5–25.0°
α = 87.175 (2)°	µ = 0.63 mm^−1
β = 78.856 (2)°	T = 173 K
γ = 81.474 (2)°	Plate, pink
V = 762.61 (19) Å^3	0.19 × 0.17 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer	2786 independent reflections
Radiation source: fine-focus sealed tube	2032 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
ϕ and ω scans	θmax = 25.4°, θmin = 2.0°
Absorption correction: multi-scan (TWINABS; Sheldrick, 2003)	h = −6→6
Tmin = 0.676, Tmax = 0.745	k = −12→12
13385 measured reflections	l = 0→15

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)] = 0.093	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.228	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0164P)^2 + 9.3P] where P = (Fo^2 + 2Fc^2)/3
2786 reflections	(Δ/σ)max < 0.001
179 parameters	Δρmax = 0.71 e Å^−3
0 restraints	Δρmin = −0.89 e Å^−3

Special details

Experimental. TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

For component 1: wR2(int) was 0.0549 before and 0.0460 after correction. The Ratio of minimum to maximum transmission is 0.91. The λ/2 correction factor is Not present

For component 2: wR2(int) was 0.0664 before and 0.0469 after correction. The Ratio of minimum to maximum transmission not present. The λ/2 correction factor is Not present

Final HKLF 4 output contains 13385 reflections, Rint = 0.0533 (6718 with I > 3sig(I), Rint = 0.0400)

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	0.5000	0.0000	0.0000	0.0217 (4)
O4	0.8245 (8)	0.0527 (5)	−0.0875 (4)	0.0259 (11)
H4A	0.9116	0.0861	−0.0468	0.039*
H4B	0.7974	0.1148	−0.1372	0.039*
O1	0.2947 (8)	0.1293 (4)	−0.0851 (4)	0.0284 (12)
O2	0.5742 (10)	0.1838 (6)	−0.2164 (4)	0.0437 (15)
O3	−0.0339 (10)	0.3206 (5)	−0.1427 (5)	0.0442 (15)
N1	0.4646 (10)	0.1467 (5)	0.1144 (5)	0.0262 (14)
N2	0.1474 (11)	0.4777 (6)	0.4001 (5)	0.0335 (15)
C13	0.3664 (14)	0.1882 (7)	−0.1687 (6)	0.0318 (18)
C12	0.1723 (15)	0.2740 (8)	−0.2163 (7)	0.043 (2)
H12A	0.2401	0.3498	−0.2528	0.052*
H12B	0.1244	0.2227	−0.2684	0.052*
C10	−0.0057 (15)	0.4091 (8)	−0.0716 (8)	0.042 (2)
C9	−0.2010 (14)	0.4424 (8)	0.0052 (8)	0.042 (2)
H9	−0.3397	0.4018	0.0088	0.051*
C5	0.6335 (14)	0.1602 (8)	0.1688 (7)	0.038 (2)
H5	0.7780	0.1009	0.1571	0.046*
C1	0.2635 (13)	0.2314 (7)	0.1348 (6)	0.0335 (18)
H1	0.1390	0.2231	0.0988	0.040*
C6	0.3746 (14)	0.4588 (9)	0.3307 (6)	0.0380 (19)
H6A	0.5028	0.4440	0.3719	0.046*
H6B	0.3944	0.5396	0.2883	0.046*
C8	0.1075 (14)	0.6027 (8)	0.4482 (6)	0.0378 (19)
H8A	0.1156	0.6725	0.3939	0.045*
H8B	0.2350	0.6077	0.4878	0.045*
C7	0.1316 (15)	0.3748 (8)	0.4801 (6)	0.040 (2)
H7A	0.2605	0.3745	0.5200	0.048*
H7B	0.1524	0.2886	0.4475	0.048*
C11	0.1974 (15)	0.4660 (8)	−0.0770 (7)	0.042 (2)
H11	0.3332	0.4424	−0.1295	0.051*
C2	0.2273 (13)	0.3304 (7)	0.2053 (6)	0.0305 (17)
H2	0.0812	0.3883	0.2166	0.037*
C3	0.4032 (13)	0.3448 (7)	0.2590 (6)	0.0301 (17)
C4	0.6070 (14)	0.2550 (8)	0.2401 (7)	0.043 (2)
H4	0.7311	0.2593	0.2773	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0171 (7)	0.0232 (7)	0.0226 (8)	0.0000 (5)	−0.0008 (5)	−0.0004 (5)
O4	0.022 (3)	0.031 (3)	0.025 (3)	−0.006 (2)	−0.003 (2)	0.008 (2)
O1	0.027 (3)	0.022 (2)	0.036 (3)	0.002 (2)	−0.011 (2)	0.003 (2)
O2	0.036 (3)	0.059 (4)	0.035 (3)	−0.018 (3)	−0.001 (3)	0.022 (3)
O3	0.035 (3)	0.037 (3)	0.066 (4)	−0.006 (3)	−0.024 (3)	0.007 (3)
N1	0.021 (3)	0.023 (3)	0.031 (4)	0.001 (2)	0.000 (3)	−0.002 (3)
N2	0.036 (4)	0.035 (4)	0.026 (4)	0.001 (3)	−0.001 (3)	−0.004 (3)
C13	0.037 (5)	0.033 (4)	0.027 (4)	−0.010 (4)	−0.009 (4)	0.007 (3)
C12	0.046 (5)	0.043 (5)	0.046 (6)	−0.021 (4)	−0.017 (4)	0.028 (4)
C10	0.036 (5)	0.027 (4)	0.070 (7)	−0.010 (4)	−0.024 (4)	0.019 (4)
C9	0.023 (4)	0.028 (4)	0.078 (7)	−0.004 (3)	−0.019 (4)	0.012 (4)
C5	0.028 (4)	0.041 (5)	0.047 (5)	0.004 (4)	−0.012 (4)	−0.013 (4)
C1	0.027 (4)	0.034 (4)	0.037 (5)	0.009 (3)	−0.010 (3)	−0.003 (3)
C6	0.035 (4)	0.054 (5)	0.025 (4)	−0.010 (4)	0.000 (3)	−0.012 (4)
C8	0.035 (5)	0.040 (5)	0.034 (5)	0.001 (4)	−0.001 (4)	0.004 (4)
C7	0.038 (5)	0.040 (5)	0.039 (5)	0.014 (4)	−0.012 (4)	−0.009 (4)
C11	0.033 (5)	0.035 (5)	0.059 (6)	−0.004 (4)	−0.010 (4)	0.009 (4)
C2	0.024 (4)	0.033 (4)	0.030 (4)	0.008 (3)	−0.001 (3)	−0.002 (3)
C3	0.027 (4)	0.034 (4)	0.025 (4)	−0.008 (3)	0.008 (3)	0.000 (3)
C4	0.027 (4)	0.045 (5)	0.058 (6)	0.002 (4)	−0.012 (4)	−0.019 (4)

Geometric parameters (Å, º)

Co1—O4	2.131 (4)	C9—H9	0.9500
Co1—O4^i	2.131 (4)	C9—C11^ii	1.375 (12)
Co1—O1	2.084 (5)	C5—H5	0.9500
Co1—O1^i	2.084 (5)	C5—C4	1.363 (11)
Co1—N1	2.151 (6)	C1—H1	0.9500
Co1—N1^i	2.151 (6)	C1—C2	1.382 (10)
O4—H4A	0.9131	C6—H6A	0.9900
O4—H4B	0.9130	C6—H6B	0.9900
O1—C13	1.260 (9)	C6—C3	1.517 (10)
O2—C13	1.237 (9)	C8—H8A	0.9900
O3—C12	1.421 (11)	C8—H8B	0.9900
O3—C10	1.388 (10)	C8—C7^iii	1.508 (11)
N1—C5	1.343 (10)	C7—C8^iii	1.508 (11)
N1—C1	1.337 (9)	C7—H7A	0.9900
N2—C6	1.440 (10)	C7—H7B	0.9900
N2—C8	1.435 (10)	C11—C9^ii	1.375 (12)
N2—C7	1.461 (10)	C11—H11	0.9500
C13—C12	1.535 (11)	C2—H2	0.9500
C12—H12A	0.9900	C2—C3	1.373 (11)
C12—H12B	0.9900	C3—C4	1.376 (11)
C10—C9	1.376 (13)	C4—H4	0.9500
C10—C11	1.377 (11)
O4—Co1—O4^i	180.0	C11^ii—C9—C10	120.6 (8)
O4—Co1—N1^i	85.7 (2)	C11^ii—C9—H9	119.7
O4^i—Co1—N1^i	94.3 (2)	N1—C5—H5	118.5
O4—Co1—N1	94.3 (2)	N1—C5—C4	123.0 (7)
O4^i—Co1—N1	85.7 (2)	C4—C5—H5	118.5
O1^i—Co1—O4	87.77 (19)	N1—C1—H1	118.2
O1—Co1—O4^i	87.77 (18)	N1—C1—C2	123.5 (7)
O1^i—Co1—O4^i	92.23 (19)	C2—C1—H1	118.2
O1—Co1—O4	92.23 (19)	N2—C6—H6A	108.9
O1^i—Co1—O1	180.0	N2—C6—H6B	108.9
O1^i—Co1—N1^i	90.1 (2)	N2—C6—C3	113.4 (7)
O1—Co1—N1	90.1 (2)	H6A—C6—H6B	107.7
O1^i—Co1—N1	89.9 (2)	C3—C6—H6A	108.9
O1—Co1—N1^i	89.9 (2)	C3—C6—H6B	108.9
N1—Co1—N1^i	180.0 (3)	N2—C8—H8A	109.3
Co1—O4—H4A	112.0	N2—C8—H8B	109.3
Co1—O4—H4B	111.7	N2—C8—C7^iii	111.8 (7)
H4A—O4—H4B	106.8	H8A—C8—H8B	107.9
C13—O1—Co1	127.2 (5)	C7^iii—C8—H8A	109.3
C10—O3—C12	116.7 (7)	C7^iii—C8—H8B	109.3
C5—N1—Co1	124.3 (5)	N2—C7—C8^iii	110.0 (6)
C1—N1—Co1	119.6 (5)	N2—C7—H7A	109.7
C1—N1—C5	116.2 (6)	N2—C7—H7B	109.7
C6—N2—C7	111.1 (6)	C8^iii—C7—H7A	109.7
C8—N2—C6	110.9 (7)	C8^iii—C7—H7B	109.7
C8—N2—C7	109.3 (6)	H7A—C7—H7B	108.2
O1—C13—C12	115.8 (7)	C10—C11—H11	120.5
O2—C13—O1	127.3 (7)	C9^ii—C11—C10	119.1 (9)
O2—C13—C12	116.9 (7)	C9^ii—C11—H11	120.5
O3—C12—C13	113.7 (7)	C1—C2—H2	120.1
O3—C12—H12A	108.8	C3—C2—C1	119.8 (7)
O3—C12—H12B	108.8	C3—C2—H2	120.1
C13—C12—H12A	108.8	C2—C3—C6	120.6 (7)
C13—C12—H12B	108.8	C2—C3—C4	116.6 (7)
H12A—C12—H12B	107.7	C4—C3—C6	122.8 (7)
C9—C10—O3	115.6 (7)	C5—C4—C3	121.0 (8)
C9—C10—C11	120.3 (9)	C5—C4—H4	119.5
C11—C10—O3	124.1 (9)	C3—C4—H4	119.5
C10—C9—H9	119.7
Co1—O1—C13—O2	−1.8 (12)	N1—C1—C2—C3	−0.3 (12)
Co1—O1—C13—C12	177.7 (5)	N2—C6—C3—C2	48.1 (10)
Co1—N1—C5—C4	179.3 (7)	N2—C6—C3—C4	−135.2 (8)
Co1—N1—C1—C2	−178.6 (6)	C12—O3—C10—C9	−173.6 (7)
O4—Co1—O1—C13	12.3 (6)	C12—O3—C10—C11	8.8 (11)
O4^i—Co1—O1—C13	−167.7 (6)	C10—O3—C12—C13	66.9 (9)
O4^i—Co1—N1—C5	125.5 (6)	C9—C10—C11—C9^ii	−0.8 (13)
O4—Co1—N1—C5	−54.5 (6)	C5—N1—C1—C2	1.5 (12)
O4—Co1—N1—C1	125.6 (6)	C1—N1—C5—C4	−0.8 (12)
O4^i—Co1—N1—C1	−54.4 (6)	C1—C2—C3—C6	175.3 (7)
O1^i—Co1—N1—C5	33.2 (6)	C1—C2—C3—C4	−1.6 (12)
O1—Co1—N1—C5	−146.8 (6)	C6—N2—C8—C7^iii	179.1 (7)
O1—Co1—N1—C1	33.3 (6)	C6—N2—C7—C8^iii	179.8 (7)
O1^i—Co1—N1—C1	−146.7 (6)	C6—C3—C4—C5	−174.6 (8)
O1—C13—C12—O3	26.2 (10)	C8—N2—C6—C3	−166.4 (7)
O2—C13—C12—O3	−154.2 (7)	C8—N2—C7—C8^iii	57.0 (10)
O3—C10—C9—C11^ii	−176.9 (7)	C7—N2—C6—C3	71.8 (9)
O3—C10—C11—C9^ii	176.7 (7)	C7—N2—C8—C7^iii	−58.1 (9)
N1—Co1—O1—C13	106.6 (6)	C11—C10—C9—C11^ii	0.8 (13)
N1^i—Co1—O1—C13	−73.4 (6)	C2—C3—C4—C5	2.2 (13)
N1—C5—C4—C3	−1.1 (14)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O1^iv	0.91	2.28	2.945 (7)	130
O4—H4B···O2	0.91	1.85	2.636 (7)	143

Symmetry code: (iv) x+1, y, z.