Bis(2,6-di­methyl­anilinium) di­aqua­bis­(di­hydrogen diphosphato-κ2O,O′)cobaltate(II)

Saad, A.B.; Selmi, A.; Rzaigui, M.; Akriche, S.T.

doi:10.1107/S1600536814002530

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 3| March 2014| Pages m86-m87

doi:10.1107/S1600536814002530

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Bis(2,6-dimethylanilinium) diaquabis(dihydrogen diphosphato-κ²O,O′)cobaltate(II)

Ahlem Ben Saad,^a Ahmed Selmi,^a ^* Mohamed Rzaigui ^a and Samah Toumi Akriche ^a

^aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia
^*Correspondence e-mail: ahmedselmi09@yahoo.fr

(Received 3 February 2014; accepted 4 February 2014; online 8 February 2014)

In the title compound, (C₈H₁₂N)₂[Co(H₂P₂O₇)₂(H₂O)₂], the Co²⁺ ion lies on a crystallographic inversion centre and adopts a slightly distorted octahedral CoO₆ coordination geometry arising from two chelating diphosphate [H₂P₂O₇]²⁻ ligands and two trans water molecules. In the crystal, the components are linked by O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds and weak aromatic π–π stacking [shortest centroid–centroid separation = 3.778 (2) Å] interactions. (001) layers of alternating organic cations and complex inorganic anions are apparent.

CCDC reference: 984995

Related literature

For related structures, see: Ahmed et al. (2006 ); Selmi et al. (2006 , 2009 ); Gharbi et al. (1994 ); Gharbi & Jouini (2004 ); Elboulali et al. (2013a ,b ); Essehli et al. (2006 ).

Experimental

Crystal data

(C₈H₁₂N)₂[Co(H₂P₂O₇)₂(H₂O)₂]
M_r = 691.25
Triclinic, $[P \overline 1]$
a = 7.320 (3) Å
b = 7.584 (4) Å
c = 13.413 (2) Å
α = 85.35 (3)°
β = 75.56 (2)°
γ = 74.42 (5)°
V = 694.5 (5) Å³
Z = 1
Ag Kα radiation
λ = 0.56087 Å
μ = 0.48 mm⁻¹
T = 293 K
0.40 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.799, T_max = 0.982
9085 measured reflections
6683 independent reflections
5514 reflections with I > 2σ(I)
R_int = 0.080
2 standard reflections every 120 min intensity decay: 5%

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.168
S = 1.04
6683 reflections
189 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.57 e Å⁻³
Δρ_min = −0.82 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—O5	2.0645 (18)
Co1—O1	2.0744 (17)
Co1—O1W	2.130 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O6ⁱ	0.82	1.72	2.532 (3)	174
O7—H7⋯O3ⁱⁱ	0.82	1.70	2.505 (3)	167
O1W—H2W1⋯O4ⁱ	0.87 (2)	2.11 (2)	2.947 (3)	161 (4)
O1W—H1W1⋯O7ⁱⁱⁱ	0.86 (2)	1.96 (2)	2.813 (3)	177 (4)
N1—H1C⋯O6^iv	0.89	1.94	2.828 (3)	175
N1—H1A⋯O3ⁱⁱ	0.89	1.93	2.805 (3)	168
N1—H1B⋯O5	0.89	2.29	3.005 (3)	138
N1—H1B⋯O1^v	0.89	2.37	3.016 (3)	129
C7—H7C⋯O2ⁱⁱ	0.96	2.58	3.497 (5)	160
C7—H7A⋯O6^iv	0.96	2.57	3.343 (4)	138
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y+2, -z+1; (iii) x, y-1, z; (iv) x-1, y, z; (v) -x+1, -y+1, -z+1.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ); 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, 2012 ) and DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

CCDC reference: 984995

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814002530/hb7194sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814002530/hb7194Isup2.hkl

checkCIF report

Comment top

The present work is a part of our investigation of diphosphate materials of mixed organic-metal cations. Here, we report a new synthesized one: (C₈H₁₂N)₂[Co(H₂P₂O₇)₂(H₂O)₂] (I).

The asymmetric unit of (I) is made up of a half of mononuclear [Co(H₂P₂O₇)₂(H₂O)₂]^2- moiety and one of 2,6-xylidinium cation. As Co²⁺ ion lie on inversion centre, the complete formula unit is generated by this element of symmetry (Fig. 1).

The inorganic component is made up of anionic monomeric units of formula [Co(H₂P₂O₇)₂(H₂O)₂]^2-, in which the six-coordinated cobalt (II) ions are linked by means of O—H···O (with 2.505 (3) Å < O···O < 2.947 (3) Å see Table 1) hydrogen bonds to develop anionic layers running perpendicular to c axis. Similar [M(H₂P₂O₇)₂(H₂O)₂]^2n- two-dimensional topological framework can be also found in the previously reported diphosphate materials (Selmi et al., 2006, 2009; Elboulali et al., 2013a,b). The cobalt (II) complex adopts a distorted octahedral where the four O atoms of diphospahte bidentate ligand (O1, O5, O1ⁱ and O5ⁱ with (i); -x + 1, -y + 1, -z + 1) fill the equatorial positions and the two symmetry equivalent O atoms of water molecules (O1W, O1Wⁱ with (i); -x + 1, -y + 1, -z + 1) occupy the apical ones. The bond distances and angles in CoO₆ are sufficiently close to those found in the related M^IIO₆ complexes featuring the chelating diphosphate ligand (Ahmed et al., 2006; Elboulali et al., 2013a, 2013b; Essehli et al., 2006; Gharbi et al., 1994; Gharbi et al., 2004; Selmi et al., 2006 and 2009).

Two phosphorous atoms are tetrahedrally coordinated and covalently linked through O4 to form a P₂O₇ group with bent geometry (P1–O4–P2 = 129.66 (12) °) and quasi-eclipsed conformation as confirmed by the torsion angle values 11.66°, 5.76° and 7.16° respectively of O5—P2—P1—O1, O7—P2—P1—O3 and O6—P2—P1—O2.

In the crystal of 1, the 2,6-xylidinium cations are linked by means N—H···O and C—H···O hydrogen bonds to inorganic layers thanks to NH₃ group of the protonated cations (Fig. 2). It's to be noted that two adjacent cations interact by weak π···π stacking interactions (values of the inter-planar distances of 3.778 (2) Å).

Related literature top

For related structures, see: Ahmed et al. (2006); Selmi et al. (2006, 2009); Gharbi et al. (1994, 2004); Gharbi & Jouini (2004); Elboulali et al. (2013a,b); Essehli et al. (2006).

Experimental top

Pink blocks of the title compound were grown at room temperature by slow evaporation from water-ethanol (80/20) solution containing a stoichiometric mixture of CoCl₂·6H₂O (0.12 mg, 0.5 mmol), 2,6-xylidine (0.12 mL,1 mmol) and N₄P₂O₇.10H₂O (0.45 mg, 1 mmol) dissolved in 2 ml of hydrochloric acid solution (2M).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1996); 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, 2012) and DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. An ORTEP view of (I) with displacement ellipsoids drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. Hydrogen bonds are represented as dashed lines. [Symmetry code: (i) 1 - x, 1 - y, 1 - z.]
	Fig. 2. Perspetive view of crystal packing of (I). The H-atoms not involved in H-bonding are omitted.

Bis(2,6-dimethylanilinium) diaquabis(dihydrogen diphosphato-κ²O,O')cobaltate(II) top

Crystal data top

(C₈H₁₂N)₂[Co(H₂P₂O₇)₂(H₂O)₂]	Z = 1
M_r = 691.25	F(000) = 357
Triclinic, P1	D_x = 1.653 Mg m⁻³
a = 7.320 (3) Å	Ag Kα radiation, λ = 0.56087 Å
b = 7.584 (4) Å	Cell parameters from 25 reflections
c = 13.413 (2) Å	θ = 9–11°
α = 85.35 (3)°	µ = 0.48 mm⁻¹
β = 75.56 (2)°	T = 293 K
γ = 74.42 (5)°	Prism, pink
V = 694.5 (5) Å³	0.40 × 0.30 × 0.20 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	5514 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.080
Graphite monochromator	θ_max = 28.0°, θ_min = 2.2°
non–profiled ω scans	h = −12→12
Absorption correction: ψ scan (North et al., 1968)	k = −12→12
T_min = 0.799, T_max = 0.982	l = −5→22
9085 measured reflections	2 standard reflections every 120 min
6683 independent reflections	intensity decay: 5%

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.168	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0826P)² + 0.9452P] where P = (F_o² + 2F_c²)/3
6683 reflections	(Δ/σ)_max = 0.005
189 parameters	Δρ_max = 1.57 e Å⁻³
3 restraints	Δρ_min = −0.82 e Å⁻³

Crystal data top

(C₈H₁₂N)₂[Co(H₂P₂O₇)₂(H₂O)₂]	γ = 74.42 (5)°
M_r = 691.25	V = 694.5 (5) Å³
Triclinic, P1	Z = 1
a = 7.320 (3) Å	Ag Kα radiation, λ = 0.56087 Å
b = 7.584 (4) Å	µ = 0.48 mm⁻¹
c = 13.413 (2) Å	T = 293 K
α = 85.35 (3)°	0.40 × 0.30 × 0.20 mm
β = 75.56 (2)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	5514 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.080
T_min = 0.799, T_max = 0.982	2 standard reflections every 120 min
9085 measured reflections	intensity decay: 5%
6683 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	3 restraints
wR(F²) = 0.168	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 1.57 e Å⁻³
6683 reflections	Δρ_min = −0.82 e Å⁻³
189 parameters

Special details top

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	0.5000	0.5000	0.01796 (9)
P1	0.69129 (7)	0.72084 (7)	0.63065 (4)	0.01948 (10)
P2	0.80524 (7)	0.75466 (7)	0.40670 (4)	0.01867 (10)
O1	0.5727 (2)	0.5931 (2)	0.62242 (13)	0.0242 (3)
O2	0.8322 (3)	0.6463 (2)	0.70245 (15)	0.0287 (3)
H2	0.8794	0.5361	0.6937	0.043*
O3	0.5808 (3)	0.9121 (2)	0.66208 (16)	0.0306 (4)
O4	0.8430 (2)	0.7284 (3)	0.52092 (14)	0.0274 (3)
O5	0.6535 (2)	0.6611 (2)	0.40048 (13)	0.0245 (3)
O6	1.0029 (2)	0.6880 (2)	0.33643 (15)	0.0281 (3)
O7	0.7321 (3)	0.9654 (2)	0.39394 (17)	0.0308 (4)
H7	0.6270	0.9903	0.3778	0.046*
O1W	0.7487 (2)	0.2730 (2)	0.49181 (18)	0.0327 (4)
H1W1	0.748 (6)	0.178 (4)	0.462 (3)	0.049*
H2W1	0.865 (4)	0.291 (5)	0.477 (3)	0.049*
N1	0.3681 (3)	0.7717 (3)	0.26576 (15)	0.0258 (3)
H1A	0.3675	0.8804	0.2865	0.039*
H1B	0.4577	0.6849	0.2885	0.039*
H1C	0.2511	0.7508	0.2908	0.039*
C1	0.4143 (4)	0.7700 (4)	0.15241 (18)	0.0291 (4)
C2	0.2798 (5)	0.8852 (4)	0.1038 (2)	0.0367 (5)
C3	0.3238 (7)	0.8820 (6)	−0.0032 (3)	0.0530 (9)
H3	0.2364	0.9570	−0.0382	0.064*
C4	0.4949 (8)	0.7695 (7)	−0.0583 (2)	0.0616 (12)
H4	0.5210	0.7680	−0.1298	0.074*
C5	0.6260 (6)	0.6602 (6)	−0.0078 (2)	0.0540 (10)
H5	0.7416	0.5865	−0.0457	0.065*
C6	0.5902 (5)	0.6569 (4)	0.0994 (2)	0.0378 (6)
C7	0.0963 (5)	1.0126 (5)	0.1621 (3)	0.0477 (7)
H7A	0.0077	0.9431	0.1985	0.072*
H7B	0.0364	1.0961	0.1147	0.072*
H7C	0.1273	1.0802	0.2102	0.072*
C8	0.7374 (5)	0.5355 (6)	0.1532 (3)	0.0556 (9)
H8A	0.8042	0.6090	0.1783	0.083*
H8B	0.8302	0.4477	0.1057	0.083*
H8C	0.6715	0.4726	0.2100	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.01549 (15)	0.01757 (15)	0.02352 (17)	−0.00720 (11)	−0.00640 (12)	−0.00003 (12)
P1	0.0174 (2)	0.01835 (19)	0.0248 (2)	−0.00437 (15)	−0.00820 (16)	−0.00249 (16)
P2	0.01319 (18)	0.01767 (19)	0.0260 (2)	−0.00567 (14)	−0.00438 (15)	−0.00018 (16)
O1	0.0256 (7)	0.0265 (7)	0.0252 (7)	−0.0133 (5)	−0.0071 (5)	−0.0016 (5)
O2	0.0286 (7)	0.0271 (7)	0.0330 (8)	−0.0007 (6)	−0.0171 (6)	−0.0051 (6)
O3	0.0286 (7)	0.0206 (6)	0.0450 (10)	−0.0003 (6)	−0.0174 (7)	−0.0082 (6)
O4	0.0206 (6)	0.0389 (8)	0.0276 (7)	−0.0137 (6)	−0.0087 (5)	0.0010 (6)
O5	0.0236 (6)	0.0279 (7)	0.0279 (7)	−0.0154 (5)	−0.0083 (5)	0.0032 (5)
O6	0.0176 (6)	0.0248 (7)	0.0369 (9)	−0.0044 (5)	0.0010 (6)	0.0012 (6)
O7	0.0235 (7)	0.0185 (6)	0.0539 (11)	−0.0040 (5)	−0.0166 (7)	−0.0014 (6)
O1W	0.0191 (6)	0.0259 (7)	0.0549 (12)	−0.0031 (6)	−0.0118 (7)	−0.0099 (7)
N1	0.0265 (8)	0.0297 (8)	0.0232 (8)	−0.0104 (7)	−0.0062 (6)	0.0003 (6)
C1	0.0362 (11)	0.0345 (10)	0.0227 (9)	−0.0204 (9)	−0.0061 (8)	0.0002 (8)
C2	0.0475 (14)	0.0433 (13)	0.0310 (11)	−0.0272 (12)	−0.0166 (10)	0.0089 (10)
C3	0.078 (3)	0.068 (2)	0.0340 (14)	−0.045 (2)	−0.0286 (16)	0.0146 (14)
C4	0.099 (3)	0.080 (3)	0.0228 (12)	−0.057 (3)	−0.0082 (16)	0.0011 (14)
C5	0.070 (2)	0.065 (2)	0.0286 (13)	−0.0376 (19)	0.0110 (14)	−0.0132 (13)
C6	0.0413 (13)	0.0433 (13)	0.0295 (11)	−0.0205 (11)	0.0030 (10)	−0.0084 (10)
C7	0.0455 (16)	0.0484 (17)	0.0554 (19)	−0.0149 (13)	−0.0249 (15)	0.0147 (14)
C8	0.0376 (15)	0.061 (2)	0.057 (2)	−0.0017 (15)	0.0009 (14)	−0.0131 (17)

Geometric parameters (Å, º) top

Co1—O5ⁱ	2.0645 (18)	N1—H1B	0.8900
Co1—O5	2.0645 (18)	N1—H1C	0.8900
Co1—O1	2.0744 (17)	C1—C2	1.386 (4)
Co1—O1ⁱ	2.0744 (17)	C1—C6	1.396 (4)
Co1—O1Wⁱ	2.130 (2)	C2—C3	1.391 (4)
Co1—O1W	2.130 (2)	C2—C7	1.500 (5)
P1—O1	1.4905 (17)	C3—C4	1.383 (7)
P1—O3	1.495 (2)	C3—H3	0.9300
P1—O2	1.5505 (18)	C4—C5	1.369 (7)
P1—O4	1.6151 (19)	C4—H4	0.9300
P2—O5	1.4910 (17)	C5—C6	1.395 (4)
P2—O6	1.4971 (18)	C5—H5	0.9300
P2—O7	1.5529 (19)	C6—C8	1.509 (6)
P2—O4	1.6110 (19)	C7—H7A	0.9600
O2—H2	0.8200	C7—H7B	0.9600
O7—H7	0.8200	C7—H7C	0.9600
O1W—H1W1	0.856 (18)	C8—H8A	0.9600
O1W—H2W1	0.867 (18)	C8—H8B	0.9600
N1—C1	1.473 (3)	C8—H8C	0.9600
N1—H1A	0.8900

O5ⁱ—Co1—O5	180.0	C1—N1—H1B	109.5
O5ⁱ—Co1—O1	90.34 (7)	H1A—N1—H1B	109.5
O5—Co1—O1	89.66 (7)	C1—N1—H1C	109.5
O5ⁱ—Co1—O1ⁱ	89.66 (7)	H1A—N1—H1C	109.5
O5—Co1—O1ⁱ	90.34 (7)	H1B—N1—H1C	109.5
O1—Co1—O1ⁱ	180.0	C2—C1—C6	123.4 (3)
O5ⁱ—Co1—O1Wⁱ	93.83 (8)	C2—C1—N1	117.4 (2)
O5—Co1—O1Wⁱ	86.17 (8)	C6—C1—N1	119.2 (2)
O1—Co1—O1Wⁱ	92.18 (8)	C1—C2—C3	117.1 (3)
O1ⁱ—Co1—O1Wⁱ	87.82 (8)	C1—C2—C7	122.5 (3)
O5ⁱ—Co1—O1W	86.17 (8)	C3—C2—C7	120.4 (3)
O5—Co1—O1W	93.83 (8)	C4—C3—C2	121.2 (4)
O1—Co1—O1W	87.82 (8)	C4—C3—H3	119.4
O1ⁱ—Co1—O1W	92.18 (8)	C2—C3—H3	119.4
O1Wⁱ—Co1—O1W	180.0	C5—C4—C3	120.0 (3)
O1—P1—O3	116.44 (11)	C5—C4—H4	120.0
O1—P1—O2	112.85 (11)	C3—C4—H4	120.0
O3—P1—O2	107.98 (11)	C4—C5—C6	121.5 (4)
O1—P1—O4	108.32 (10)	C4—C5—H5	119.2
O3—P1—O4	108.67 (12)	C6—C5—H5	119.2
O2—P1—O4	101.45 (10)	C5—C6—C1	116.8 (3)
O5—P2—O6	116.77 (11)	C5—C6—C8	120.5 (3)
O5—P2—O7	111.33 (10)	C1—C6—C8	122.8 (3)
O6—P2—O7	109.58 (11)	C2—C7—H7A	109.5
O5—P2—O4	109.55 (9)	C2—C7—H7B	109.5
O6—P2—O4	104.85 (10)	H7A—C7—H7B	109.5
O7—P2—O4	103.77 (11)	C2—C7—H7C	109.5
P1—O1—Co1	133.68 (10)	H7A—C7—H7C	109.5
P1—O2—H2	109.5	H7B—C7—H7C	109.5
P2—O4—P1	129.66 (11)	C6—C8—H8A	109.5
P2—O5—Co1	134.76 (11)	C6—C8—H8B	109.5
P2—O7—H7	109.5	H8A—C8—H8B	109.5
Co1—O1W—H1W1	116 (3)	C6—C8—H8C	109.5
Co1—O1W—H2W1	120 (3)	H8A—C8—H8C	109.5
H1W1—O1W—H2W1	111 (3)	H8B—C8—H8C	109.5
C1—N1—H1A	109.5

O3—P1—O1—Co1	99.39 (16)	O1—Co1—O5—P2	17.64 (15)
O2—P1—O1—Co1	−134.89 (14)	O1ⁱ—Co1—O5—P2	−162.36 (15)
O4—P1—O1—Co1	−23.38 (17)	O1Wⁱ—Co1—O5—P2	109.84 (16)
O5ⁱ—Co1—O1—P1	178.85 (15)	O1W—Co1—O5—P2	−70.16 (16)
O5—Co1—O1—P1	−1.15 (15)	C6—C1—C2—C3	1.6 (4)
O1ⁱ—Co1—O1—P1	10 (100)	N1—C1—C2—C3	−179.6 (2)
O1Wⁱ—Co1—O1—P1	−87.30 (15)	C6—C1—C2—C7	−176.8 (3)
O1W—Co1—O1—P1	92.70 (15)	N1—C1—C2—C7	2.0 (4)
O5—P2—O4—P1	−35.28 (19)	C1—C2—C3—C4	−0.4 (5)
O6—P2—O4—P1	−161.35 (15)	C7—C2—C3—C4	178.1 (3)
O7—P2—O4—P1	83.69 (17)	C2—C3—C4—C5	−0.9 (6)
O1—P1—O4—P2	47.67 (18)	C3—C4—C5—C6	1.0 (6)
O3—P1—O4—P2	−79.70 (17)	C4—C5—C6—C1	0.1 (5)
O2—P1—O4—P2	166.66 (15)	C4—C5—C6—C8	−179.8 (4)
O6—P2—O5—Co1	114.85 (16)	C2—C1—C6—C5	−1.5 (4)
O7—P2—O5—Co1	−118.29 (16)	N1—C1—C6—C5	179.7 (2)
O4—P2—O5—Co1	−4.09 (18)	C2—C1—C6—C8	178.5 (3)
O5ⁱ—Co1—O5—P2	−89 (100)	N1—C1—C6—C8	−0.3 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O6ⁱⁱ	0.82	1.72	2.532 (3)	174
O7—H7···O3ⁱⁱⁱ	0.82	1.70	2.505 (3)	167
O1W—H2W1···O4ⁱⁱ	0.87 (2)	2.11 (2)	2.947 (3)	161 (4)
O1W—H1W1···O7^iv	0.86 (2)	1.96 (2)	2.813 (3)	177 (4)
N1—H1C···O6^v	0.89	1.94	2.828 (3)	175
N1—H1A···O3ⁱⁱⁱ	0.89	1.93	2.805 (3)	168
N1—H1B···O5	0.89	2.29	3.005 (3)	138
N1—H1B···O1ⁱ	0.89	2.37	3.016 (3)	129
C7—H7C···O2ⁱⁱⁱ	0.96	2.58	3.497 (5)	160
C7—H7A···O6^v	0.96	2.57	3.343 (4)	138

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1; (iii) −x+1, −y+2, −z+1; (iv) x, y−1, z; (v) x−1, y, z.

Selected bond lengths (Å) top

Co1—O5	2.0645 (18)	Co1—O1W	2.130 (2)
Co1—O1	2.0744 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O6ⁱ	0.82	1.72	2.532 (3)	174
O7—H7···O3ⁱⁱ	0.82	1.70	2.505 (3)	167
O1W—H2W1···O4ⁱ	0.867 (18)	2.11 (2)	2.947 (3)	161 (4)
O1W—H1W1···O7ⁱⁱⁱ	0.856 (18)	1.958 (18)	2.813 (3)	177 (4)
N1—H1C···O6^iv	0.89	1.94	2.828 (3)	175
N1—H1A···O3ⁱⁱ	0.89	1.93	2.805 (3)	168
N1—H1B···O5	0.89	2.29	3.005 (3)	138
N1—H1B···O1^v	0.89	2.37	3.016 (3)	129
C7—H7C···O2ⁱⁱ	0.96	2.58	3.497 (5)	160
C7—H7A···O6^iv	0.96	2.57	3.343 (4)	138

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+2, −z+1; (iii) x, y−1, z; (iv) x−1, y, z; (v) −x+1, −y+1, −z+1.

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