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]

Sample, A.D.; LaDuca, R.L.

doi:10.1107/S1600536814008745

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Pages m198-m199

doi:10.1107/S1600536814008745

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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]

Alexander D. Sample ^a and Robert L. LaDuca ^a ^*

^aLyman Briggs College, Department of Chemistry, Michigan State University, East Lansing, MI 48825, USA
^*Correspondence e-mail: laduca@msu.edu

(Received 15 April 2014; accepted 17 April 2014; online 3 May 2014)

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.

CCDC reference: 997809

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 4-bpmp, see: Farnum et al. (2013 ).

Experimental

Crystal data

[Co(C₁₀H₈O₆)(C₁₆H₂₀N₄)(H₂O)₂]·5H₂O
M_r = 677.57
Triclinic, $[P \overline 1]$
a = 5.7727 (8) Å
b = 10.3421 (15) Å
c = 13.1675 (19) Å
α = 87.175 (2)°
β = 78.856 (2)°
γ = 81.474 (2)°
V = 762.61 (19) Å³
Z = 1
Mo Kα radiation
μ = 0.63 mm⁻¹
T = 173 K
0.19 × 0.17 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (TWINABS; Sheldrick, 2003 ) T_min = 0.676, T_max = 0.745
13385 measured reflections
2786 independent reflections
2032 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.093
wR(F²) = 0.228
S = 1.10
2786 reflections
179 parameters
H-atom parameters constrained
Δρ_max = 0.71 e Å⁻³
Δρ_min = −0.89 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O1ⁱ	0.91	2.28	2.945 (7)	130
O4—H4B⋯O2	0.91	1.85	2.636 (7)	143
Symmetry code: (i) x+1, y, z.

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.

Supporting information

CCDC reference: 997809

Crystal structure: contains datablocks I, pub. DOI: 10.1107/S1600536814008745/tk5308sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814008745/tk5308Isup2.hkl

checkCIF report

Chemical context top

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.

Structural commentary top

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.

Supramolecular features top

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.

Database survey top

This compound was not previously reported in the CCDC.

Synthesis and crystallization top

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.

Refinement top

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 top

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 top

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 top

	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] top

Crystal data top

[Co(C₁₀H₈O₆)(C₁₆H₂₀N₄)(H₂O)₂]·5H₂O	Z = 1
M_r = 677.57	F(000) = 357
Triclinic, P1	D_x = 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) Å³	0.19 × 0.17 × 0.05 mm

Data collection top

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

Refinement top

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)] = 0.093	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.228	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0164P)² + 9.3P] where P = (F_o² + 2F_c²)/3
2786 reflections	(Δ/σ)_max < 0.001
179 parameters	Δρ_max = 0.71 e Å⁻³
0 restraints	Δρ_min = −0.89 e Å⁻³

Crystal data top

[Co(C₁₀H₈O₆)(C₁₆H₂₀N₄)(H₂O)₂]·5H₂O	γ = 81.474 (2)°
M_r = 677.57	V = 762.61 (19) Å³
Triclinic, P1	Z = 1
a = 5.7727 (8) Å	Mo Kα radiation
b = 10.3421 (15) Å	µ = 0.63 mm⁻¹
c = 13.1675 (19) Å	T = 173 K
α = 87.175 (2)°	0.19 × 0.17 × 0.05 mm
β = 78.856 (2)°

Data collection top

Bruker APEXII CCD diffractometer	2786 independent reflections
Absorption correction: multi-scan (TWINABS; Sheldrick, 2003)	2032 reflections with I > 2σ(I)
T_min = 0.676, T_max = 0.745	R_int = 0.053
13385 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.093	0 restraints
wR(F²) = 0.228	H-atom parameters constrained
S = 1.10	Δρ_max = 0.71 e Å⁻³
2786 reflections	Δρ_min = −0.89 e Å⁻³
179 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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) top

Co1—O4	2.131 (4)	C9—H9	0.9500
Co1—O4ⁱ	2.131 (4)	C9—C11ⁱⁱ	1.375 (12)
Co1—O1	2.084 (5)	C5—H5	0.9500
Co1—O1ⁱ	2.084 (5)	C5—C4	1.363 (11)
Co1—N1	2.151 (6)	C1—H1	0.9500
Co1—N1ⁱ	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—C7ⁱⁱⁱ	1.508 (11)
N1—C5	1.343 (10)	C7—C8ⁱⁱⁱ	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—C9ⁱⁱ	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—O4ⁱ	180.0	C11ⁱⁱ—C9—C10	120.6 (8)
O4—Co1—N1ⁱ	85.7 (2)	C11ⁱⁱ—C9—H9	119.7
O4ⁱ—Co1—N1ⁱ	94.3 (2)	N1—C5—H5	118.5
O4—Co1—N1	94.3 (2)	N1—C5—C4	123.0 (7)
O4ⁱ—Co1—N1	85.7 (2)	C4—C5—H5	118.5
O1ⁱ—Co1—O4	87.77 (19)	N1—C1—H1	118.2
O1—Co1—O4ⁱ	87.77 (18)	N1—C1—C2	123.5 (7)
O1ⁱ—Co1—O4ⁱ	92.23 (19)	C2—C1—H1	118.2
O1—Co1—O4	92.23 (19)	N2—C6—H6A	108.9
O1ⁱ—Co1—O1	180.0	N2—C6—H6B	108.9
O1ⁱ—Co1—N1ⁱ	90.1 (2)	N2—C6—C3	113.4 (7)
O1—Co1—N1	90.1 (2)	H6A—C6—H6B	107.7
O1ⁱ—Co1—N1	89.9 (2)	C3—C6—H6A	108.9
O1—Co1—N1ⁱ	89.9 (2)	C3—C6—H6B	108.9
N1—Co1—N1ⁱ	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—C7ⁱⁱⁱ	111.8 (7)
H4A—O4—H4B	106.8	H8A—C8—H8B	107.9
C13—O1—Co1	127.2 (5)	C7ⁱⁱⁱ—C8—H8A	109.3
C10—O3—C12	116.7 (7)	C7ⁱⁱⁱ—C8—H8B	109.3
C5—N1—Co1	124.3 (5)	N2—C7—C8ⁱⁱⁱ	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)	C8ⁱⁱⁱ—C7—H7A	109.7
C8—N2—C6	110.9 (7)	C8ⁱⁱⁱ—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)	C9ⁱⁱ—C11—C10	119.1 (9)
O2—C13—C12	116.9 (7)	C9ⁱⁱ—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)
O4ⁱ—Co1—O1—C13	−167.7 (6)	C10—O3—C12—C13	66.9 (9)
O4ⁱ—Co1—N1—C5	125.5 (6)	C9—C10—C11—C9ⁱⁱ	−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)
O4ⁱ—Co1—N1—C1	−54.4 (6)	C1—C2—C3—C6	175.3 (7)
O1ⁱ—Co1—N1—C5	33.2 (6)	C1—C2—C3—C4	−1.6 (12)
O1—Co1—N1—C5	−146.8 (6)	C6—N2—C8—C7ⁱⁱⁱ	179.1 (7)
O1—Co1—N1—C1	33.3 (6)	C6—N2—C7—C8ⁱⁱⁱ	179.8 (7)
O1ⁱ—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—C8ⁱⁱⁱ	57.0 (10)
O3—C10—C9—C11ⁱⁱ	−176.9 (7)	C7—N2—C6—C3	71.8 (9)
O3—C10—C11—C9ⁱⁱ	176.7 (7)	C7—N2—C8—C7ⁱⁱⁱ	−58.1 (9)
N1—Co1—O1—C13	106.6 (6)	C11—C10—C9—C11ⁱⁱ	0.8 (13)
N1ⁱ—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) top

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.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O1ⁱ	0.91	2.28	2.945 (7)	130
O4—H4B···O2	0.91	1.85	2.636 (7)	143

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

Acknowledgements

We gratefully acknowledge Lyman Briggs College of Michigan State University for funding this work.

References

Bruker (2012). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 70| Part 6| June 2014| Pages m198-m199

doi:10.1107/S1600536814008745

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