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Acta Cryst. (2011). E67, m985-m986    [ doi:10.1107/S1600536811023518 ]

Piperazine-1,4-diium bis(pyridine-2,6-dicarboxylato-[kappa]3O2,N,O6)cobaltate(II) tetrahydrate

A. Raissi Shabari, N. Ghoddoosi, M. Pourayoubi and S. Moradi

Abstract top

The asymmetric unit of the title complex, (C4H12N2)[Co(C7H3NO4)2]·4H2O, consists of one piperazinediium dication, one [Co(py-2,6-dc)2]2- dianion (where py-2,6-dc is pyridine-2,6-dicarboxylate) and four water molecules. The piperazinediium cation adopts a chair conformation and the CoII ion is six-coordinated in an N2O4 environment, having a distorted octahedral geometry. In the crystal, intermolecular O-H...O, N-H...O and weak C-H...O hydrogen bonds link the components, forming a three-dimensional network.

Comment top

The structure determination of title compound was performed as a part of a project on the synthesis of new proton-transfer compounds (Raissi Shabari et al., 2010).

The Co atom in title compound adopts a distorted octahedral coordination arising from four oxygen and two nitrogen atoms of two pyridine-2,6-dicarboxylato ligands, Fig. 1. The Co—O and Co—N bond lengths are similar to those in a recently published bis(pyridine-2,6-dicarboxylato)cobaltate(II) complex, (C6H10N2)[Co(C7H3NO4)2].5H2O (Pasdar et al., 2011). The organic dication adopts a typical chair geometry with normal bond lengths and angles (Sutherland & Harrison, 2009; Allen et al., 1995).

The protonated piperazine nitrogen atoms are involved in positive charge assisted (Gilli et al., 1994) N—H···O hydrogen bonds, atom N3 is involved with the O atoms of an adjacent carbonyl of one pyridine-2,6-dicarboxylato ligand and a neighbouring H2O molecule and atom N4 with two pyridine-2,6-dicarboxylato ligands in two neighbouring complexes.

Cations, anions and four crystallographically independent H2O molecules are hydrogen bonded in a three-dimensional network through N—H···O, O—H···O and weak C—H···O hydrogen bonds (Table 1).

Related literature top

The structure determination of title compound was performed as a part of our

project on the synthesis of new proton-transfer compounds, see: Raissi Shabari et al. (2010). For bond lengths in a related cobaltate(II) complex, see: Pasdar et al. (2011). For bond lengths and angles in piperazinediium dications, see: Sutherland & Harrison (2009); Allen et al. (1995). For positive-charge-assisted hydrogen bonds, see: Gilli et al. (1994).

Experimental top

A solution of Co(NO3)2.6H2O (2 mmol) in H2O was added to a solution of pyridine-2,6-dicarboxylic acid (4 mmol) in H2O and stirred (45 minutes) at room temperature. To the resulting solution, a solution of piperazine (4 mmol) in H2O was added and stirred (4 h) at 323 K. Suitable single crystals for X-ray analysis were obtained after slow evaporation at room temperature. IR (KBr, ν, cm-1): 3425, 3240, 3013, 3001, 2725, 2467, 1608, 1568, 1425, 1371, 1279, 1182, 1074, 1036, 914, 824, 760, 733, 692, 677, 592, 534.

Refinement top

H atoms of water molecules and N—H groups of cation were found in a difference Fourier map and refined isotropically. Carbon-bound H-atoms were placed in calculated positions, C—H = 0.93 Å (aromatic) and 0.97 Å (CH2), and were included in the refinement using a riding-model approximation, with Uiso = 1.2Ueq (C).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); 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, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and enCIFer (Allen et al., 2004).

Figures top
[Figure 1] Fig. 1. Molecular structure and atom labeling scheme for title complex with displacement ellipsoids drawn at the 50% probability level.
Piperazine-1,4-diium bis(pyridine-2,6-dicarboxylato- κ3O2,N,O6)cobaltate(II) tetrahydrate top
Crystal data top
(C4H12N2)[Co(C7H3NO4)2]·4H2OF(000) = 1140
Mr = 549.36Dx = 1.628 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6018 reflections
a = 7.9537 (16) Åθ = 2.5–29.1°
b = 13.420 (3) ŵ = 0.84 mm−1
c = 21.004 (4) ÅT = 150 K
β = 90.55 (3)°Plate, pink
V = 2241.8 (8) Å30.5 × 0.4 × 0.15 mm
Z = 4
Data collection top
Stoe IPDS 2T
diffractometer		6018 independent reflections
Radiation source: fine-focus sealed tube5226 reflections with I > 2σ(I)
graphiteRint = 0.038
Detector resolution: 0.15 mm pixels mm-1θmax = 29.1°, θmin = 2.5°
rotation method scansh = −10→10
Absorption correction: numerical
shape of crystal determined optically		k = −16→18
Tmin = 0.670, Tmax = 0.878l = −24→28
15339 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0326P)2 + 1.2111P]
where P = (Fo2 + 2Fc2)/3
6018 reflections(Δ/σ)max = 0.001
364 parametersΔρmax = 0.48 e Å−3
0 restraintsΔρmin = −0.33 e Å−3
Crystal data top
(C4H12N2)[Co(C7H3NO4)2]·4H2OV = 2241.8 (8) Å3
Mr = 549.36Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.9537 (16) ŵ = 0.84 mm−1
b = 13.420 (3) ÅT = 150 K
c = 21.004 (4) Å0.5 × 0.4 × 0.15 mm
β = 90.55 (3)°
Data collection top
Stoe IPDS 2T
diffractometer		6018 independent reflections
Absorption correction: numerical
shape of crystal determined optically		5226 reflections with I > 2σ(I)
Tmin = 0.670, Tmax = 0.878Rint = 0.038
15339 measured reflectionsθmax = 29.1°
Refinement top
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.077Δρmax = 0.48 e Å−3
S = 1.07Δρmin = −0.33 e Å−3
6018 reflectionsAbsolute structure: ?
364 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
O100.26226 (16)0.55638 (11)0.28084 (7)0.0288 (3)
Co10.73056 (2)0.745668 (14)0.504511 (9)0.01278 (6)
C181.08242 (19)0.81672 (13)0.23202 (8)0.0195 (3)
H18A1.12800.76590.20430.023*
H18B1.16240.87120.23440.023*
C160.76380 (18)0.73170 (12)0.26866 (7)0.0173 (3)
H16A0.68280.67770.26670.021*
H16B0.71850.78360.29570.021*
C150.92728 (19)0.69397 (11)0.29675 (7)0.0176 (3)
H15A0.90910.67140.34000.021*
H15B0.96700.63780.27200.021*
C170.9172 (2)0.85410 (12)0.20509 (8)0.0197 (3)
H17A0.87590.90830.23110.024*
H17B0.93390.87930.16230.024*
N40.79141 (16)0.77200 (10)0.20359 (6)0.0165 (2)
N31.05640 (16)0.77441 (11)0.29680 (6)0.0175 (3)
O50.91680 (15)0.73565 (8)0.58111 (5)0.0206 (2)
N10.71594 (14)0.89536 (9)0.51050 (6)0.0128 (2)
O40.53764 (14)0.77007 (8)0.57578 (5)0.0188 (2)
O20.89349 (14)0.79723 (8)0.43015 (5)0.0191 (2)
O80.57909 (14)0.68290 (8)0.42961 (5)0.0187 (2)
C70.53098 (18)0.85856 (11)0.59591 (7)0.0145 (3)
C60.62806 (17)0.93522 (11)0.55788 (7)0.0132 (3)
C90.86203 (17)0.56523 (11)0.56247 (7)0.0128 (3)
C130.69018 (17)0.53516 (11)0.47424 (7)0.0124 (3)
O30.44917 (14)0.88780 (9)0.64298 (5)0.0190 (2)
O10.95932 (14)0.93309 (8)0.37446 (5)0.0188 (2)
O70.51331 (14)0.53761 (9)0.38257 (6)0.0218 (2)
N20.76472 (14)0.59801 (9)0.51494 (6)0.0116 (2)
C140.58397 (18)0.58788 (11)0.42379 (7)0.0148 (3)
C80.94256 (18)0.64790 (11)0.60154 (7)0.0149 (3)
C20.80213 (17)0.95197 (11)0.46993 (7)0.0128 (3)
C50.62615 (19)1.03742 (11)0.56736 (7)0.0159 (3)
H50.56641.06520.60080.019*
C120.71303 (17)0.43292 (11)0.47966 (7)0.0147 (3)
H120.66220.38920.45100.018*
C100.88885 (18)0.46439 (11)0.57169 (7)0.0163 (3)
H100.95510.44170.60540.020*
C10.89276 (17)0.89032 (11)0.42059 (7)0.0147 (3)
C30.80328 (18)1.05509 (11)0.47560 (7)0.0151 (3)
H30.86101.09460.44680.018*
C110.81438 (18)0.39770 (11)0.52927 (7)0.0169 (3)
H110.83220.32960.53400.020*
C40.71541 (19)1.09736 (11)0.52577 (8)0.0172 (3)
H40.71651.16610.53150.021*
O90.37881 (15)0.76948 (10)0.33746 (7)0.0244 (3)
O61.02757 (14)0.62407 (9)0.64909 (6)0.0223 (2)
O110.9680 (2)0.87887 (11)0.67821 (7)0.0312 (3)
O120.46115 (18)0.06341 (10)0.71858 (6)0.0260 (3)
H3B1.157 (3)0.7514 (16)0.3122 (11)0.029 (6)*
H4B0.828 (3)0.7228 (18)0.1787 (11)0.029 (6)*
H3A1.022 (3)0.8243 (18)0.3232 (11)0.031 (6)*
H4A0.694 (3)0.7923 (19)0.1846 (11)0.034 (6)*
H9B0.437 (3)0.7419 (18)0.3625 (12)0.031 (6)*
H10B0.324 (4)0.561 (2)0.3103 (15)0.050 (8)*
H10A0.321 (3)0.582 (2)0.2501 (14)0.051 (8)*
H9A0.432 (4)0.815 (2)0.3200 (14)0.052 (8)*
H12A0.508 (3)0.050 (2)0.7517 (14)0.051 (8)*
H12B0.464 (3)0.013 (2)0.6991 (14)0.045 (8)*
H11B0.950 (3)0.838 (2)0.6492 (14)0.046 (7)*
H11A0.989 (3)0.929 (2)0.6591 (13)0.046 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O100.0222 (6)0.0391 (8)0.0252 (7)−0.0005 (5)−0.0045 (5)0.0017 (6)
Co10.01592 (9)0.00943 (9)0.01298 (10)0.00047 (7)−0.00079 (6)0.00003 (7)
C180.0185 (7)0.0244 (8)0.0158 (7)−0.0038 (6)0.0021 (5)−0.0007 (6)
C160.0154 (6)0.0188 (7)0.0177 (7)0.0008 (5)0.0014 (5)−0.0008 (5)
C150.0211 (7)0.0161 (7)0.0156 (7)0.0040 (5)−0.0001 (5)0.0027 (5)
C170.0262 (8)0.0165 (7)0.0165 (7)−0.0008 (6)−0.0016 (6)0.0040 (6)
N40.0158 (6)0.0190 (6)0.0147 (6)0.0039 (5)−0.0044 (5)0.0003 (5)
N30.0149 (6)0.0247 (7)0.0128 (6)0.0044 (5)−0.0024 (5)−0.0024 (5)
O50.0275 (6)0.0138 (5)0.0202 (5)−0.0027 (4)−0.0086 (4)−0.0010 (4)
N10.0126 (5)0.0118 (5)0.0140 (6)0.0001 (4)0.0003 (4)0.0004 (4)
O40.0240 (5)0.0130 (5)0.0194 (5)−0.0025 (4)0.0056 (4)−0.0011 (4)
O20.0243 (5)0.0142 (5)0.0188 (5)0.0013 (4)0.0063 (4)−0.0001 (4)
O80.0235 (5)0.0147 (5)0.0177 (5)0.0013 (4)−0.0082 (4)0.0011 (4)
C70.0156 (6)0.0153 (7)0.0126 (6)−0.0003 (5)−0.0003 (5)0.0021 (5)
C60.0149 (6)0.0127 (6)0.0120 (6)0.0004 (5)0.0000 (5)0.0002 (5)
C90.0113 (6)0.0143 (6)0.0129 (6)−0.0016 (5)−0.0012 (5)0.0005 (5)
C130.0113 (6)0.0139 (6)0.0120 (6)0.0000 (5)−0.0007 (5)−0.0011 (5)
O30.0236 (5)0.0180 (5)0.0154 (5)−0.0002 (4)0.0067 (4)0.0003 (4)
O10.0230 (5)0.0181 (5)0.0154 (5)−0.0018 (4)0.0053 (4)0.0013 (4)
O70.0243 (6)0.0231 (6)0.0179 (5)0.0034 (4)−0.0092 (4)−0.0060 (4)
N20.0111 (5)0.0121 (5)0.0117 (5)−0.0002 (4)−0.0005 (4)0.0004 (4)
C140.0140 (6)0.0180 (7)0.0123 (6)0.0026 (5)−0.0014 (5)0.0002 (5)
C80.0137 (6)0.0170 (7)0.0139 (6)−0.0036 (5)−0.0013 (5)−0.0015 (5)
C20.0120 (6)0.0138 (6)0.0124 (6)0.0002 (5)−0.0004 (5)0.0012 (5)
C50.0191 (6)0.0145 (7)0.0141 (6)0.0000 (5)0.0005 (5)−0.0031 (5)
C120.0143 (6)0.0124 (6)0.0173 (7)−0.0019 (5)−0.0009 (5)−0.0031 (5)
C100.0152 (6)0.0163 (7)0.0174 (7)0.0002 (5)−0.0033 (5)0.0045 (5)
C10.0133 (6)0.0168 (7)0.0142 (6)−0.0007 (5)−0.0003 (5)−0.0014 (5)
C30.0160 (6)0.0126 (6)0.0168 (7)−0.0020 (5)−0.0004 (5)0.0018 (5)
C110.0178 (6)0.0109 (6)0.0221 (7)0.0002 (5)−0.0009 (6)0.0024 (5)
C40.0204 (7)0.0109 (6)0.0202 (7)−0.0016 (5)−0.0003 (6)−0.0007 (5)
O90.0182 (5)0.0233 (6)0.0315 (7)0.0007 (5)−0.0089 (5)0.0059 (5)
O60.0243 (5)0.0227 (6)0.0196 (6)−0.0062 (4)−0.0116 (4)0.0031 (5)
O110.0541 (9)0.0202 (6)0.0195 (6)−0.0074 (6)0.0038 (6)−0.0005 (5)
O120.0400 (7)0.0204 (6)0.0175 (6)0.0034 (5)−0.0031 (5)−0.0012 (5)
Geometric parameters (Å, °) top
O10—H10B0.79 (3)O8—C141.2817 (19)
O10—H10A0.87 (3)C7—O31.2518 (19)
Co1—N22.0117 (13)C7—C61.518 (2)
Co1—N12.0162 (13)C6—C51.386 (2)
Co1—O82.1446 (12)C9—N21.3321 (18)
Co1—O22.1532 (13)C9—C101.383 (2)
Co1—O42.1787 (13)C9—C81.518 (2)
Co1—O52.1807 (13)C13—N21.3357 (18)
C18—N31.491 (2)C13—C121.389 (2)
C18—C171.511 (2)C13—C141.5229 (19)
C18—H18A0.9700O1—C11.2485 (19)
C18—H18B0.9700O7—C141.2293 (18)
C16—N41.488 (2)C8—O61.2426 (18)
C16—C151.510 (2)C2—C31.389 (2)
C16—H16A0.9700C2—C11.514 (2)
C16—H16B0.9700C5—C41.388 (2)
C15—N31.490 (2)C5—H50.9300
C15—H15A0.9700C12—C111.394 (2)
C15—H15B0.9700C12—H120.9300
C17—N41.488 (2)C10—C111.391 (2)
C17—H17A0.9700C10—H100.9300
C17—H17B0.9700C3—C41.391 (2)
N4—H4B0.89 (2)C3—H30.9300
N4—H4A0.91 (2)C11—H110.9300
N3—H3B0.91 (2)C4—H40.9300
N3—H3A0.91 (2)O9—H9B0.79 (3)
O5—C81.2692 (19)O9—H9A0.83 (3)
N1—C61.3335 (19)O11—H11B0.83 (3)
N1—C21.3358 (19)O11—H11A0.81 (3)
O4—C71.2619 (18)O12—H12A0.80 (3)
O2—C11.2652 (19)O12—H12B0.79 (3)
H10B—O10—H10A103 (3)C6—N1—Co1118.50 (10)
N2—Co1—N1169.23 (5)C2—N1—Co1119.77 (10)
N2—Co1—O876.55 (5)C7—O4—Co1113.82 (10)
N1—Co1—O8113.87 (5)C1—O2—Co1115.50 (10)
N2—Co1—O2108.30 (5)C14—O8—Co1116.32 (9)
N1—Co1—O276.15 (5)O3—C7—O4125.69 (14)
O8—Co1—O286.10 (5)O3—C7—C6118.30 (13)
N2—Co1—O499.70 (5)O4—C7—C6115.99 (13)
N1—Co1—O476.46 (5)N1—C6—C5120.71 (14)
O8—Co1—O499.71 (5)N1—C6—C7113.19 (12)
O2—Co1—O4151.99 (4)C5—C6—C7126.06 (13)
N2—Co1—O576.63 (4)N2—C9—C10121.04 (13)
N1—Co1—O593.13 (4)N2—C9—C8113.76 (13)
O8—Co1—O5152.85 (4)C10—C9—C8125.15 (13)
O2—Co1—O598.38 (5)N2—C13—C12120.96 (13)
O4—Co1—O588.87 (5)N2—C13—C14113.07 (12)
N3—C18—C17109.89 (13)C12—C13—C14125.97 (13)
N3—C18—H18A109.7C9—N2—C13121.49 (13)
C17—C18—H18A109.7C9—N2—Co1118.93 (10)
N3—C18—H18B109.7C13—N2—Co1119.58 (10)
C17—C18—H18B109.7O7—C14—O8126.80 (14)
H18A—C18—H18B108.2O7—C14—C13118.81 (13)
N4—C16—C15110.28 (12)O8—C14—C13114.39 (12)
N4—C16—H16A109.6O6—C8—O5126.53 (14)
C15—C16—H16A109.6O6—C8—C9118.02 (13)
N4—C16—H16B109.6O5—C8—C9115.43 (13)
C15—C16—H16B109.6N1—C2—C3120.99 (14)
H16A—C16—H16B108.1N1—C2—C1112.12 (12)
N3—C15—C16110.38 (12)C3—C2—C1126.89 (13)
N3—C15—H15A109.6C6—C5—C4118.47 (14)
C16—C15—H15A109.6C6—C5—H5120.8
N3—C15—H15B109.6C4—C5—H5120.8
C16—C15—H15B109.6C13—C12—C11118.08 (13)
H15A—C15—H15B108.1C13—C12—H12121.0
N4—C17—C18110.13 (13)C11—C12—H12121.0
N4—C17—H17A109.6C9—C10—C11118.40 (13)
C18—C17—H17A109.6C9—C10—H10120.8
N4—C17—H17B109.6C11—C10—H10120.8
C18—C17—H17B109.6O1—C1—O2125.15 (14)
H17A—C17—H17B108.1O1—C1—C2119.23 (13)
C16—N4—C17110.77 (12)O2—C1—C2115.62 (13)
C16—N4—H4B108.8 (15)C2—C3—C4117.93 (14)
C17—N4—H4B109.6 (15)C2—C3—H3121.0
C16—N4—H4A112.4 (15)C4—C3—H3121.0
C17—N4—H4A110.8 (16)C10—C11—C12120.02 (14)
H4B—N4—H4A104 (2)C10—C11—H11120.0
C15—N3—C18112.15 (12)C12—C11—H11120.0
C15—N3—H3B110.8 (14)C5—C4—C3120.28 (14)
C18—N3—H3B109.0 (14)C5—C4—H4119.9
C15—N3—H3A108.6 (14)C3—C4—H4119.9
C18—N3—H3A108.7 (15)H9B—O9—H9A110 (2)
H3B—N3—H3A107 (2)H11B—O11—H11A103 (3)
C8—O5—Co1114.39 (9)H12A—O12—H12B104 (3)
C6—N1—C2121.59 (13)
N4—C16—C15—N356.04 (16)C8—C9—N2—Co1−2.77 (16)
N3—C18—C17—N4−57.15 (17)C12—C13—N2—C9−0.7 (2)
C15—C16—N4—C17−58.43 (16)C14—C13—N2—C9179.69 (12)
C18—C17—N4—C1659.08 (16)C12—C13—N2—Co1179.15 (11)
C16—C15—N3—C18−55.72 (17)C14—C13—N2—Co1−0.48 (16)
C17—C18—N3—C1556.17 (17)N1—Co1—N2—C9−12.6 (3)
N2—Co1—O5—C8−8.50 (11)O8—Co1—N2—C9−178.50 (11)
N1—Co1—O5—C8168.13 (11)O2—Co1—N2—C9100.29 (11)
O8—Co1—O5—C8−17.59 (17)O4—Co1—N2—C9−80.74 (11)
O2—Co1—O5—C8−115.43 (11)O5—Co1—N2—C95.75 (10)
O4—Co1—O5—C891.75 (11)N1—Co1—N2—C13167.6 (2)
N2—Co1—N1—C6−59.3 (3)O8—Co1—N2—C131.66 (10)
O8—Co1—N1—C6105.67 (11)O2—Co1—N2—C13−79.55 (11)
O2—Co1—N1—C6−175.04 (11)O4—Co1—N2—C1399.42 (11)
O4—Co1—N1—C610.90 (10)O5—Co1—N2—C13−174.09 (11)
O5—Co1—N1—C6−77.18 (11)Co1—O8—C14—O7−176.49 (13)
N2—Co1—N1—C2116.5 (3)Co1—O8—C14—C133.39 (16)
O8—Co1—N1—C2−78.56 (11)N2—C13—C14—O7177.88 (14)
O2—Co1—N1—C20.73 (10)C12—C13—C14—O7−1.7 (2)
O4—Co1—N1—C2−173.33 (11)N2—C13—C14—O8−2.00 (18)
O5—Co1—N1—C298.59 (11)C12—C13—C14—O8178.38 (14)
N2—Co1—O4—C7156.74 (10)Co1—O5—C8—O6−171.44 (13)
N1—Co1—O4—C7−12.98 (10)Co1—O5—C8—C99.52 (16)
O8—Co1—O4—C7−125.39 (10)N2—C9—C8—O6175.91 (13)
O2—Co1—O4—C7−25.34 (16)C10—C9—C8—O6−6.8 (2)
O5—Co1—O4—C780.51 (11)N2—C9—C8—O5−4.96 (19)
N2—Co1—O2—C1−176.16 (10)C10—C9—C8—O5172.35 (14)
N1—Co1—O2—C1−6.37 (10)C6—N1—C2—C3−0.1 (2)
O8—Co1—O2—C1109.39 (11)Co1—N1—C2—C3−175.70 (10)
O4—Co1—O2—C16.00 (17)C6—N1—C2—C1179.60 (12)
O5—Co1—O2—C1−97.55 (11)Co1—N1—C2—C13.96 (15)
N2—Co1—O8—C14−2.85 (11)N1—C6—C5—C41.1 (2)
N1—Co1—O8—C14180.00 (10)C7—C6—C5—C4−176.42 (13)
O2—Co1—O8—C14107.02 (11)N2—C13—C12—C110.8 (2)
O4—Co1—O8—C14−100.60 (11)C14—C13—C12—C11−179.66 (13)
O5—Co1—O8—C146.25 (17)N2—C9—C10—C111.3 (2)
Co1—O4—C7—O3−168.85 (12)C8—C9—C10—C11−175.84 (14)
Co1—O4—C7—C612.83 (16)Co1—O2—C1—O1−169.47 (12)
C2—N1—C6—C5−1.3 (2)Co1—O2—C1—C210.27 (16)
Co1—N1—C6—C5174.37 (11)N1—C2—C1—O1170.25 (13)
C2—N1—C6—C7176.50 (12)C3—C2—C1—O1−10.1 (2)
Co1—N1—C6—C7−7.81 (15)N1—C2—C1—O2−9.50 (18)
O3—C7—C6—N1177.41 (13)C3—C2—C1—O2170.14 (14)
O4—C7—C6—N1−4.14 (18)N1—C2—C3—C41.6 (2)
O3—C7—C6—C5−4.9 (2)C1—C2—C3—C4−178.01 (13)
O4—C7—C6—C5173.53 (14)C9—C10—C11—C12−1.2 (2)
C10—C9—N2—C13−0.4 (2)C13—C12—C11—C100.2 (2)
C8—C9—N2—C13177.06 (12)C6—C5—C4—C30.5 (2)
C10—C9—N2—Co1179.80 (11)C2—C3—C4—C5−1.8 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O12—H12B···O3i0.79 (3)2.06 (3)2.8428 (18)174 (3)
O11—H11B···O50.83 (3)2.00 (3)2.8290 (18)177 (3)
O11—H11A···O1ii0.81 (3)2.02 (3)2.8173 (19)170 (3)
O10—H10B···O70.79 (3)2.15 (3)2.9213 (19)165 (3)
O10—H10A···O11iii0.87 (3)1.99 (3)2.854 (2)172 (3)
O9—H9B···O80.79 (3)1.96 (3)2.7521 (18)175 (2)
O9—H9A···O12iv0.83 (3)2.01 (3)2.840 (2)173 (3)
N4—H4B···O3v0.89 (2)1.92 (2)2.7973 (18)165 (2)
N4—H4A···O6iii0.91 (2)1.89 (2)2.7592 (17)161 (2)
N3—H3B···O9vi0.91 (2)1.86 (2)2.6958 (18)152 (2)
N3—H3A···O20.91 (2)2.50 (2)3.1126 (19)124.5 (18)
N3—H3A···O10.91 (2)1.88 (2)2.7957 (18)176 (2)
C18—H18B···O10vii0.972.583.457 (2)151.
C17—H17B···O7vii0.972.363.127 (2)135.
C16—H16B···O12iv0.972.523.293 (2)137.
C15—H15B···O10vi0.972.603.261 (2)126.
C15—H15A···O20.972.543.140 (2)120.
Symmetry codes: (i) x, y−1, z; (ii) −x+2, −y+2, −z+1; (iii) x−1/2, −y+3/2, z−1/2; (iv) −x+1, −y+1, −z+1; (v) x+1/2, −y+3/2, z−1/2; (vi) x+1, y, z; (vii) −x+3/2, y+1/2, −z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O12—H12B···O3i0.79 (3)2.06 (3)2.8428 (18)174 (3)
O11—H11B···O50.83 (3)2.00 (3)2.8290 (18)177 (3)
O11—H11A···O1ii0.81 (3)2.02 (3)2.8173 (19)170 (3)
O10—H10B···O70.79 (3)2.15 (3)2.9213 (19)165 (3)
O10—H10A···O11iii0.87 (3)1.99 (3)2.854 (2)172 (3)
O9—H9B···O80.79 (3)1.96 (3)2.7521 (18)175 (2)
O9—H9A···O12iv0.83 (3)2.01 (3)2.840 (2)173 (3)
N4—H4B···O3v0.89 (2)1.92 (2)2.7973 (18)165 (2)
N4—H4A···O6iii0.91 (2)1.89 (2)2.7592 (17)161 (2)
N3—H3B···O9vi0.91 (2)1.86 (2)2.6958 (18)152 (2)
N3—H3A···O20.91 (2)2.50 (2)3.1126 (19)124.5 (18)
N3—H3A···O10.91 (2)1.88 (2)2.7957 (18)176 (2)
C18—H18B···O10vii0.972.583.457 (2)151.
C17—H17B···O7vii0.972.363.127 (2)135.
C16—H16B···O12iv0.972.523.293 (2)137.
C15—H15B···O10vi0.972.603.261 (2)126.
C15—H15A···O20.972.543.140 (2)120.
Symmetry codes: (i) x, y−1, z; (ii) −x+2, −y+2, −z+1; (iii) x−1/2, −y+3/2, z−1/2; (iv) −x+1, −y+1, −z+1; (v) x+1/2, −y+3/2, z−1/2; (vi) x+1, y, z; (vii) −x+3/2, y+1/2, −z+1/2.
Acknowledgements top

Support of this investigation by the North Tehran Branch, Islamic Azad University, is gratefully acknowledged.

references
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