Bis(2-meth­oxy­benzyl­ammonium) di­aqua­bis­(di­hydrogen diphosphato-κ2O,O′)cobaltate(II) dihydrate

Elboulali, A.; Selmi, A.; Ratel-Ramond, N.; Rzaigui, M.; Akriche, S.T.

doi:10.1107/S1600536814006102

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 4| April 2014| Pages m145-m146

doi:10.1107/S1600536814006102

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Bis(2-methoxybenzylammonium) diaquabis(dihydrogen diphosphato-κ²O,O′)cobaltate(II) dihydrate

Adel Elboulali,^a Ahmed Selmi,^a ^* Nicolas Ratel-Ramond,^b Mohamed Rzaigui ^a and Samah Toumi Akriche ^a

^aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia, and ^bCEMES–CNRS, 29 rue Jeanne Marvig, 31055 Toulouse cedex 4, France
^*Correspondence e-mail: ahmedselmi09@yahoo.fr

(Received 12 March 2014; accepted 19 March 2014; online 26 March 2014)

The title compound, (C₈H₁₂NO)₂[Co(H₂P₂O₇)₂(H₂O)₂]·2H₂O, crystallizes isotypically with its Mn^II analogue. It consists of alternating layers of organic cations and inorganic complex anions, extending parallel to (100). The complex cobaltate(II) anion exhibits -1 symmetry. Its Co²⁺ atom has an octahedral coordination sphere, defined by two water molecules in apical positions and two H₂P₂O₇²⁻ ligands in equatorial positions. The cohesion between inorganic and organic layers is accomplished by a set of O—H⋯O and N—H⋯O hydrogen bonds involving the organic cation, the inorganic anion and the remaining lattice water molecules.

CCDC reference: 992564

Related literature

For the isotypic Mn^II structure, see: Elboulali et al. (2013b ). For related structures with diphosphate units, see: Alaoui Tahiri et al. (2003 ); Essehli et al. (2005 ); Selmi et al. (2006 , 2009 ); Ahmed et al. (2006 ); Gharbi et al. (1994 ); Gharbi & Jouini (2004 ); Elboulali et al. (2013a ). For distortion index calculations, see: Kobashi et al. (1997 ).

Experimental

Crystal data

(C₈H₁₂NO)₂[Co(H₂P₂O₇)₂(H₂O)₂]·2H₂O
M_r = 759.28
Monoclinic, P 2₁ /c
a = 14.050 (5) Å
b = 11.971 (5) Å
c = 9.161 (5) Å
β = 93.718 (5)°
V = 1537.6 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.85 mm⁻¹
T = 293 K
0.25 × 0.19 × 0.13 mm

Data collection

Nonius KappaCCD diffractometer
33422 measured reflections
4645 independent reflections
3135 reflections with I > 2σ(I)
R_int = 0.081

Refinement

R[F² > 2σ(F²)] = 0.096
wR(F²) = 0.266
S = 1.08
4645 reflections
212 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 2.59 e Å⁻³
Δρ_min = −1.26 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—O1	2.075 (4)
Co1—O1W	2.095 (4)
Co1—O5	2.124 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2ⁱ	0.82	1.85	2.553 (6)	143
O6—H6⋯O7ⁱⁱ	0.82	1.77	2.571 (6)	166
O1W—H1W1⋯O2ⁱⁱⁱ	0.86 (2)	1.98 (3)	2.827 (6)	168 (7)
O1W—H2W1⋯O7ⁱⁱ	0.86 (2)	2.00 (2)	2.851 (6)	171 (8)
N1—H1A⋯O2W	0.89	1.99	2.840 (8)	159
N1—H1A⋯O3ⁱⁱ	0.89	2.53	2.988 (7)	113
N1—H1B⋯O5^iv	0.89	2.04	2.810 (7)	145
N1—H1C⋯O1	0.89	2.28	2.944 (7)	131
N1—H1C⋯O8	0.89	2.42	2.972 (9)	120
O2W—H1W2⋯O2ⁱⁱ	0.85 (2)	2.08 (4)	2.885 (7)	157 (9)
O2W—H2W2⋯O7ⁱⁱⁱ	0.85 (2)	2.06 (4)	2.876 (7)	161 (9)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) -x+1, -y+1, -z+1.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000 ); data reduction: EVALCCD (Duisenberg et al., 2003 ); 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: 992564

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814006102/wm5011sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814006102/wm5011Isup2.hkl

checkCIF report

Comment top

As a part of our interest in diphosphate materials, we report here the preparation and the structural study of the title compound, (C₈H₁₂NO)₂[Co(H₂P₂O₇)₂(H₂O)₂]·2H₂O, (I), that crystallizes isotypically with its Mn^II analogue (Elboulali et al., 2013b).

The asymmetric unit of (I) consists of a Co(II) atom, one H₂P₂O₇^2- anion, one organic cation and two water molecules (one coordinating to Co(II) and the other a lattice water molecule). The Co(II) ion lies on an inversion centre, hence the complete formula unit is generated by this element of symmetry (Fig. 1).

The crystal structure of (I) exhibits the same type of architecture than that of the isotypic Mn^II analogue. It is built up from centrosymmetric [Co(H₂P₂O₇)₂(H₂O)₂]^2- complex anions arranged in layers parallel to (100). These laters are interconnected by a set of O—H···O and N—H···O hydrogen bonds (Table 2, Fig. 2) between the components.

The distortion index calculation (Kobashi et al., 1997) of the CoO₆ octahedron in the anion gives a value of 0.023, indicating a rather regular coordination sphere for this ion (radius 0.74 Å). The distortion index for the MnO₆ octahedron in the isotypic Mn^II analogue is with 0.028 slightly greater, probably as a consequence of the larger ionic radius of Mn^II (0.80 Å). The Co—O bond lengths around Co²⁺ ion are between 2.075 (4) and 2.124 (4) Å (Table 1), similar to those observed in (NH₄)₂[Co(H₂P₂O₇)₂(H₂O)₂] (Essehli et al., 2005) and due to the smaller ionic radius shorter than in [Mn(H₂P₂O₇)₂(H₂O)₂] units in related structures (Alaoui Tahiri et al., 2003; Elboulali et al., 2013b).

The P₂O₇ moiety has a quasi-eclipsed conformation with a mean O—P—O—P torsion angle of 19.6 ° and bridges the Co(II) ion through O1—P1 and O5—P2 linkages. The P₂O₇ group is bent, with a P1—O4—P2 bond angle of 132.9 (3)° as observed in other M(II)–organic diphosphate frameworks (Elboulali et al. 2013a; Selmi et al. 2006, 2009; Ahmed et al. 2006; Gharbi et al. 2004, 1994).

Related literature top

For the isotypic Mn^II structure, see: Elboulali et al. (2013b). For related structures with diphosphate units, see: Alaoui Tahiri et al. (2003); Essehli et al. (2005); Selmi et al. (2006, 2009); Ahmed et al. (2006); Gharbi et al. (1994); Gharbi & Jouini (2004); Elboulali et al. (2013a). For distortion index calculations, see: Kobashi et al. (1997).

Experimental top

Crystals of the title compound were obtained by the reaction of diphosphoric acid (2 mmol), CoCl₂·6H₂O (0.24 g; 1 mmol) and 2-methoxybenzylamine (0.138 g; 1 mmol) carried out in an acidic medium. Diphosphoric acid, H₄P₂O₇, was obtained from Na₄P₂O₇ by using an ion-exchange resin (Amberlite IR 120).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); 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. The molecular entities in the structure of (I) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radius. Hydrogen bonds are represented as dashed lines. [Symmetry code: (i) 1 - x, 1 - y, 1 - z.]
	Fig. 2. Perspective view of the crystal packing of (I) in a projection along [010]. The H-atoms not involved in hydrogen bonding were omitted.

Bis(2-methoxybenzylammonium) diaquabis(dihydrogen diphosphato-κ²O,O')cobaltate(II) dihydrate top

Crystal data top

(C₈H₁₂NO)₂[Co(H₂P₂O₇)₂(H₂O)₂]·2H₂O	F(000) = 786
M_r = 759.28	D_x = 1.640 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 33422 reflections
a = 14.050 (5) Å	θ = 2.2–30.9°
b = 11.971 (5) Å	µ = 0.85 mm⁻¹
c = 9.161 (5) Å	T = 293 K
β = 93.718 (5)°	Prism, pink
V = 1537.6 (12) Å³	0.25 × 0.19 × 0.13 mm
Z = 2

Data collection top

Nonius KappaCCD diffractometer	3135 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.081
Horizonally mounted graphite crystal monochromator	θ_max = 30.9°, θ_min = 2.2°
Detector resolution: 9 pixels mm^-1	h = −20→18
ω and ϕ CCD rotation images, thick slices scans	k = −17→17
33422 measured reflections	l = −10→13
4645 independent reflections

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)] = 0.096	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.266	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0687P)² + 17.5972P] where P = (F_o² + 2F_c²)/3
4645 reflections	(Δ/σ)_max = 0.003
212 parameters	Δρ_max = 2.59 e Å⁻³
7 restraints	Δρ_min = −1.26 e Å⁻³

Crystal data top

(C₈H₁₂NO)₂[Co(H₂P₂O₇)₂(H₂O)₂]·2H₂O	V = 1537.6 (12) Å³
M_r = 759.28	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.050 (5) Å	µ = 0.85 mm⁻¹
b = 11.971 (5) Å	T = 293 K
c = 9.161 (5) Å	0.25 × 0.19 × 0.13 mm
β = 93.718 (5)°

Data collection top

Nonius KappaCCD diffractometer	3135 reflections with I > 2σ(I)
33422 measured reflections	R_int = 0.081
4645 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.096	7 restraints
wR(F²) = 0.266	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0687P)² + 17.5972P] where P = (F_o² + 2F_c²)/3
4645 reflections	Δρ_max = 2.59 e Å⁻³
212 parameters	Δρ_min = −1.26 e Å⁻³

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	0.0248 (3)
P1	0.58873 (11)	0.24678 (12)	0.46988 (14)	0.0240 (3)
P2	0.38517 (11)	0.25622 (12)	0.51633 (14)	0.0249 (3)
O1	0.5946 (3)	0.3708 (3)	0.4662 (4)	0.0278 (8)
O2	0.6336 (3)	0.1843 (3)	0.3488 (4)	0.0302 (9)
O3	0.6288 (4)	0.1972 (4)	0.6168 (5)	0.0471 (13)
H3	0.6494	0.2477	0.6704	0.071*
O4	0.4796 (4)	0.2083 (4)	0.4534 (6)	0.0446 (12)
O5	0.3993 (3)	0.3764 (4)	0.5528 (5)	0.0309 (9)
O6	0.3105 (4)	0.2386 (5)	0.3853 (5)	0.0434 (12)
H6	0.3333	0.2586	0.3094	0.065*
O7	0.3549 (4)	0.1825 (4)	0.6378 (4)	0.0349 (10)
O1W	0.4616 (4)	0.4955 (4)	0.2753 (5)	0.0402 (11)
H1W1	0.441 (6)	0.558 (3)	0.240 (8)	0.060*
H2W1	0.435 (5)	0.438 (3)	0.233 (8)	0.060*
O8	0.8402 (5)	0.3749 (6)	0.5079 (7)	0.0663 (18)
N1	0.7205 (4)	0.4951 (5)	0.2793 (6)	0.0369 (12)
H1A	0.7210	0.4784	0.1847	0.055*
H1B	0.6716	0.5403	0.2934	0.055*
H1C	0.7145	0.4327	0.3307	0.055*
C1	0.8971 (5)	0.4798 (7)	0.3192 (8)	0.0454 (17)
C2	0.9128 (6)	0.3901 (7)	0.4183 (9)	0.0514 (19)
C3	0.9953 (7)	0.3286 (9)	0.4206 (12)	0.068 (3)
H3A	1.0057	0.2708	0.4875	0.082*
C4	1.0628 (8)	0.3536 (11)	0.3228 (15)	0.085 (4)
H4	1.1191	0.3126	0.3253	0.101*
C5	1.0490 (8)	0.4362 (13)	0.2235 (14)	0.087 (4)
H5	1.0952	0.4509	0.1578	0.105*
C6	0.9657 (7)	0.4997 (10)	0.2192 (11)	0.071 (3)
H6A	0.9559	0.5555	0.1493	0.085*
C7	0.8106 (5)	0.5514 (7)	0.3277 (9)	0.0474 (17)
H7A	0.8066	0.5760	0.4280	0.057*
H7B	0.8179	0.6173	0.2679	0.057*
C8	0.8535 (9)	0.2951 (13)	0.6208 (15)	0.103 (5)
H8A	0.8584	0.2220	0.5788	0.154*
H8B	0.8003	0.2973	0.6812	0.154*
H8C	0.9110	0.3118	0.6791	0.154*
O2W	0.7511 (4)	0.4927 (5)	−0.0240 (6)	0.0487 (13)
H1W2	0.732 (6)	0.435 (4)	−0.071 (9)	0.073*
H2W2	0.732 (7)	0.555 (3)	−0.061 (9)	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0412 (6)	0.0166 (5)	0.0165 (4)	0.0007 (4)	0.0011 (4)	0.0000 (4)
P1	0.0361 (8)	0.0222 (7)	0.0139 (5)	0.0062 (5)	0.0016 (5)	0.0004 (5)
P2	0.0336 (7)	0.0266 (7)	0.0144 (6)	−0.0044 (6)	0.0011 (5)	−0.0018 (5)
O1	0.031 (2)	0.0224 (19)	0.030 (2)	0.0035 (15)	0.0028 (16)	0.0026 (15)
O2	0.047 (3)	0.029 (2)	0.0150 (16)	0.0088 (17)	0.0041 (16)	−0.0026 (14)
O3	0.089 (4)	0.034 (3)	0.0170 (19)	0.015 (3)	−0.004 (2)	0.0004 (17)
O4	0.050 (3)	0.026 (2)	0.059 (3)	−0.002 (2)	0.009 (2)	−0.018 (2)
O5	0.032 (2)	0.028 (2)	0.034 (2)	0.0022 (16)	0.0104 (17)	−0.0002 (16)
O6	0.047 (3)	0.066 (3)	0.0172 (18)	−0.019 (2)	−0.0035 (18)	0.005 (2)
O7	0.057 (3)	0.029 (2)	0.0189 (18)	−0.0036 (19)	0.0000 (18)	0.0025 (15)
O1W	0.072 (3)	0.026 (2)	0.0205 (19)	0.002 (2)	−0.014 (2)	−0.0017 (16)
O8	0.058 (4)	0.087 (5)	0.052 (3)	−0.003 (3)	−0.001 (3)	0.022 (3)
N1	0.039 (3)	0.040 (3)	0.032 (3)	−0.001 (2)	0.006 (2)	−0.003 (2)
C1	0.035 (4)	0.059 (5)	0.041 (4)	−0.004 (3)	−0.006 (3)	−0.004 (3)
C2	0.039 (4)	0.058 (5)	0.054 (5)	−0.003 (3)	−0.012 (3)	−0.005 (4)
C3	0.051 (5)	0.073 (7)	0.078 (7)	0.003 (4)	−0.021 (5)	−0.013 (5)
C4	0.053 (6)	0.099 (9)	0.100 (9)	0.018 (6)	−0.006 (6)	−0.037 (8)
C5	0.062 (7)	0.130 (11)	0.072 (7)	−0.013 (7)	0.022 (5)	−0.036 (7)
C6	0.055 (6)	0.102 (8)	0.055 (5)	−0.016 (5)	0.007 (4)	−0.002 (5)
C7	0.047 (4)	0.046 (4)	0.048 (4)	0.002 (3)	−0.007 (3)	−0.002 (3)
C8	0.069 (7)	0.140 (12)	0.096 (9)	−0.025 (7)	−0.019 (6)	0.058 (9)
O2W	0.056 (3)	0.051 (3)	0.038 (3)	−0.005 (3)	−0.003 (2)	0.001 (2)

Geometric parameters (Å, º) top

Co1—O1ⁱ	2.075 (4)	N1—H1A	0.8900
Co1—O1	2.075 (4)	N1—H1B	0.8900
Co1—O1Wⁱ	2.095 (4)	N1—H1C	0.8900
Co1—O1W	2.095 (4)	C1—C6	1.393 (12)
Co1—O5	2.124 (4)	C1—C2	1.414 (12)
Co1—O5ⁱ	2.124 (4)	C1—C7	1.494 (11)
P1—O1	1.488 (4)	C2—C3	1.373 (12)
P1—O2	1.509 (4)	C3—C4	1.379 (17)
P1—O3	1.543 (4)	C3—H3A	0.9300
P1—O4	1.598 (5)	C4—C5	1.349 (18)
P2—O5	1.488 (5)	C4—H4	0.9300
P2—O7	1.503 (4)	C5—C6	1.393 (16)
P2—O6	1.556 (4)	C5—H5	0.9300
P2—O4	1.588 (5)	C6—H6A	0.9300
O3—H3	0.8200	C7—H7A	0.9700
O6—H6	0.8200	C7—H7B	0.9700
O1W—H1W1	0.86 (2)	C8—H8A	0.9600
O1W—H2W1	0.86 (2)	C8—H8B	0.9600
O8—C2	1.362 (11)	C8—H8C	0.9600
O8—C8	1.411 (12)	O2W—H1W2	0.85 (2)
N1—C7	1.477 (9)	O2W—H2W2	0.85 (2)

O1ⁱ—Co1—O1	180.0 (2)	C7—N1—H1B	109.5
O1ⁱ—Co1—O1Wⁱ	87.73 (18)	H1A—N1—H1B	109.5
O1—Co1—O1Wⁱ	92.27 (18)	C7—N1—H1C	109.5
O1ⁱ—Co1—O1W	92.27 (18)	H1A—N1—H1C	109.5
O1—Co1—O1W	87.73 (18)	H1B—N1—H1C	109.5
O1Wⁱ—Co1—O1W	180.000 (1)	C6—C1—C2	117.8 (8)
O1ⁱ—Co1—O5	92.42 (16)	C6—C1—C7	122.5 (8)
O1—Co1—O5	87.58 (16)	C2—C1—C7	119.7 (7)
O1Wⁱ—Co1—O5	85.82 (19)	O8—C2—C3	125.7 (9)
O1W—Co1—O5	94.18 (19)	O8—C2—C1	113.4 (7)
O1ⁱ—Co1—O5ⁱ	87.58 (16)	C3—C2—C1	120.9 (9)
O1—Co1—O5ⁱ	92.42 (16)	C2—C3—C4	119.3 (11)
O1Wⁱ—Co1—O5ⁱ	94.18 (19)	C2—C3—H3A	120.4
O1W—Co1—O5ⁱ	85.82 (19)	C4—C3—H3A	120.4
O5—Co1—O5ⁱ	180.00 (16)	C5—C4—C3	121.5 (11)
O1—P1—O2	116.8 (2)	C5—C4—H4	119.2
O1—P1—O3	112.7 (3)	C3—C4—H4	119.2
O2—P1—O3	107.7 (3)	C4—C5—C6	120.1 (11)
O1—P1—O4	109.8 (2)	C4—C5—H5	119.9
O2—P1—O4	103.4 (3)	C6—C5—H5	119.9
O3—P1—O4	105.4 (3)	C1—C6—C5	120.3 (11)
O5—P2—O7	116.2 (2)	C1—C6—H6A	119.9
O5—P2—O6	112.2 (3)	C5—C6—H6A	119.9
O7—P2—O6	106.4 (3)	N1—C7—C1	114.0 (6)
O5—P2—O4	109.2 (2)	N1—C7—H7A	108.7
O7—P2—O4	109.9 (3)	C1—C7—H7A	108.7
O6—P2—O4	102.0 (3)	N1—C7—H7B	108.7
P1—O1—Co1	134.7 (3)	C1—C7—H7B	108.7
P1—O3—H3	109.5	H7A—C7—H7B	107.6
P2—O4—P1	132.9 (3)	O8—C8—H8A	109.5
P2—O5—Co1	134.7 (2)	O8—C8—H8B	109.5
P2—O6—H6	109.5	H8A—C8—H8B	109.5
Co1—O1W—H1W1	114 (5)	O8—C8—H8C	109.5
Co1—O1W—H2W1	123 (5)	H8A—C8—H8C	109.5
H1W1—O1W—H2W1	114 (3)	H8B—C8—H8C	109.5
C2—O8—C8	117.6 (8)	H1W2—O2W—H2W2	116 (3)
C7—N1—H1A	109.5

O2—P1—O1—Co1	136.9 (3)	O1Wⁱ—Co1—O5—P2	−116.7 (4)
O3—P1—O1—Co1	−97.5 (4)	O1W—Co1—O5—P2	63.3 (4)
O4—P1—O1—Co1	19.7 (4)	O5ⁱ—Co1—O5—P2	−67 (100)
O1ⁱ—Co1—O1—P1	−141 (100)	C8—O8—C2—C3	5.4 (14)
O1Wⁱ—Co1—O1—P1	88.9 (4)	C8—O8—C2—C1	−173.5 (9)
O1W—Co1—O1—P1	−91.1 (4)	C6—C1—C2—O8	−177.8 (8)
O5—Co1—O1—P1	3.2 (4)	C7—C1—C2—O8	4.2 (10)
O5ⁱ—Co1—O1—P1	−176.8 (4)	C6—C1—C2—C3	3.3 (12)
O5—P2—O4—P1	23.1 (6)	C7—C1—C2—C3	−174.7 (8)
O7—P2—O4—P1	−105.4 (5)	O8—C2—C3—C4	179.9 (9)
O6—P2—O4—P1	142.0 (5)	C1—C2—C3—C4	−1.3 (14)
O1—P1—O4—P2	−39.1 (6)	C2—C3—C4—C5	−0.8 (16)
O2—P1—O4—P2	−164.5 (5)	C3—C4—C5—C6	0.8 (18)
O3—P1—O4—P2	82.6 (5)	C2—C1—C6—C5	−3.3 (14)
O7—P2—O5—Co1	140.4 (4)	C7—C1—C6—C5	174.7 (9)
O6—P2—O5—Co1	−96.9 (4)	C4—C5—C6—C1	1.3 (17)
O4—P2—O5—Co1	15.5 (5)	C6—C1—C7—N1	111.2 (9)
O1ⁱ—Co1—O5—P2	155.7 (4)	C2—C1—C7—N1	−70.9 (9)
O1—Co1—O5—P2	−24.3 (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
O3—H3···O2ⁱⁱ	0.82	1.85	2.553 (6)	143
O6—H6···O7ⁱⁱⁱ	0.82	1.77	2.571 (6)	166
O1W—H1W1···O2^iv	0.86 (2)	1.98 (3)	2.827 (6)	168 (7)
O1W—H2W1···O7ⁱⁱⁱ	0.86 (2)	2.00 (2)	2.851 (6)	171 (8)
N1—H1A···O2W	0.89	1.99	2.840 (8)	159
N1—H1A···O3ⁱⁱⁱ	0.89	2.53	2.988 (7)	113
N1—H1B···O5ⁱ	0.89	2.04	2.810 (7)	145
N1—H1C···O1	0.89	2.28	2.944 (7)	131
N1—H1C···O8	0.89	2.42	2.972 (9)	120
O2W—H1W2···O2ⁱⁱⁱ	0.85 (2)	2.08 (4)	2.885 (7)	157 (9)
O2W—H2W2···O7^iv	0.85 (2)	2.06 (4)	2.876 (7)	161 (9)

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

Selected bond lengths (Å) top

Co1—O1	2.075 (4)	Co1—O5	2.124 (4)
Co1—O1W	2.095 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.82	1.85	2.553 (6)	142.6
O6—H6···O7ⁱⁱ	0.82	1.77	2.571 (6)	166.0
O1W—H1W1···O2ⁱⁱⁱ	0.86 (2)	1.98 (3)	2.827 (6)	168 (7)
O1W—H2W1···O7ⁱⁱ	0.86 (2)	2.00 (2)	2.851 (6)	171 (8)
N1—H1A···O2W	0.89	1.99	2.840 (8)	158.6
N1—H1A···O3ⁱⁱ	0.89	2.53	2.988 (7)	112.9
N1—H1B···O5^iv	0.89	2.04	2.810 (7)	144.5
N1—H1C···O1	0.89	2.28	2.944 (7)	131.2
N1—H1C···O8	0.89	2.42	2.972 (9)	120.3
O2W—H1W2···O2ⁱⁱ	0.85 (2)	2.08 (4)	2.885 (7)	157 (9)
O2W—H2W2···O7ⁱⁱⁱ	0.85 (2)	2.06 (4)	2.876 (7)	161 (9)

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

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