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The title polymeric compound, {(C3H12N2)[Co(C10H2O8)(H2O)2]·0.5H2O}n, was obtained by the reaction of cobalt(II) nitrate hexa­hydrate with the proton-transfer compound (pnH2)2(btc)·2H2O (pn = propane-1,3-diamine and btcH4 = benzene-1,2,4,5-tetra­carboxylic acid) in aqueous solution. Each Co2+ ion is situated on a crystallographic twofold rotation axis and is coordinated in a distorted octa­hedral geometry by six O atoms [Co—O = 2.0650 (9)–2.1107 (8) Å] from two coordinated water mol­ecules and four (btc)4− ligands which also act as bridging ligands between Co2+ ions. In the crystal structure, a wide range of non-covalent inter­actions consisting of O—H...O, N—H...O and C—H...O hydrogen bonds, as well as ion pairing, van der Waals forces and C—H...π stacking between the propane-1,3-diammonium ions and the aromatic rings of benzene-1,2,4,5-tetra­carboxyl­ate ligands, connect the various fragments, forming a three-dimensional supra­molecular structure. The crystal studied was an inversion twin.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050659/om2167sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050659/om2167Isup2.hkl
Contains datablock I

CCDC reference: 667206

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • Disorder in solvent or counterion
  • R factor = 0.022
  • wR factor = 0.066
  • Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry ..... 86 PerFi
Author Response: Cation and water molecule are strongly disordered in suggested Imma space group. One of carbonyl oxygens is also disordered by two positions in Imma space group. Thus the attempt to solve disordered structure in Imma group did not lead to acceptable values of R1 and wR2.

Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.375 From the CIF: _refine_ls_abs_structure_Flack_su 0.011 PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT076_ALERT_1_C Occupancy 0.50 less than 1.0 for Sp.pos . H6B PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.34 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 7.00 Perc.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 30.00 From the CIF: _reflns_number_total 2526 Count of symmetry unique reflns 1320 Completeness (_total/calc) 191.36% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1206 Fraction of Friedel pairs measured 0.914 Are heavy atom types Z>Si present yes PLAT033_ALERT_2_G Flack Parameter Value Deviates 2 * su from zero. 0.38 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

We have reported cases in which proton transfer from benzene-1,2,4,5-tetracarboxylic acid (btcH4) to propane-1,3-diamine (pn), piperazine (pipz) and 1,10-phenanthroline (phen), resulted in the formation of novel self assembled (pnH2)2(btc).2H2O (Aghabozorg, Ghadermazi et al., 2007), (pipzH2)2(btc).6.2H2O (Aghabozorg, Manteghi, Ghadermazi 2007) and (phenH)4(btcH3)2(btcH2) (Aghabozorg, Ghadermazi & Attar Gharamaleki, 2006) systems, respectively. The resulting compounds, with some remaining sites as electron donors, can coordinate to metal ions (Aghabozorg, Ghasemikhah, Ghadermazi et al., 2006; Aghabozorg, Ghasemikhah, Soleimannejad et al., 2006). For the crystal structures of related complexes, see: Aghabozorg, Bahrami, et al., (2007); Aghabozorg, Zabihi et al., 2006; Aghabozorg, Attar Gharamaleki et al., 2007).

Here, we report a new polymeric compound obtained from reaction of (pnH2)2(btc).2H2O with cobalt(II) nitrate. The crystal structure of the title polymeric compound is shown in Fig. 1. The negative charge of the anionic complex is neutralized by dicationic propane-1,3-diammonium ions. The Co2+ atom is situated on a crystallographic twofold rotation axis.

Co2+ is six-coordinated by four (btc)4– groups and two coordinated water molecules, i.e. each (btc)4– fragments coordinates through one O atom of the (COO)- fragments, which also act as bridging ligands between other Co2+ ions. O5 and O5a atoms of two coordinated water molecules occupy the axial positions, while four O atoms of (btc)4– fragments form the equatorial plane. The axial bond is slightly longer than the equatorial bond lengths. The O5iii—Co1—O5 bond angle is slightly deviated from linearity. The coordination around Co2+ is distorted octahedral.

A considerable feature of the compound (Sharif et al., 2007) is the presence of C—H···π stacking interactions between C—H groups of (pnH2)2+ cations and aromatic rings of (btc)4– fragments (Fig. 2). The most important feature of the crystal structure is the presence of a large number of O—H···O, N—H···O and C—H···O hydrogen bonds between (pnH2)2+ and [Co(H2O)2(btc)]2– fragments and uncoordinated water molecules with D···A distances ranging from 2.679 (1) Å to 3.251 (2) Å. Hydrogen bonding, ion pairing, C—H···π stacking and van der Waals forces are effective in the stabilization of the crystal structure, resulting in the formation of an interesting supramolecular structure (Fig. 3).

Related literature top

For related literature, see: Aghabozorg, Attar Gharamaleki et al. (2007); Aghabozorg, Bahrami et al. (2007); Aghabozorg, Ghadermazi & Attar Gharamaleki (2006); Aghabozorg, Ghadermazi et al. (2007); Aghabozorg, Ghasemikhah, Ghadermazi et al. (2006); Aghabozorg, Ghasemikhah, Soleimannejad et al. (2006); Aghabozorg, Manteghi & Ghadermazi (2007); Aghabozorg, Zabihi et al. (2006); Sharif et al. (2007).

Experimental top

The proton-transfer compound was prepared by a reaction between propane-1,3-diamine and benzene-1,2,4,5-tetracarboxylic acid [Aghabozorg, Ghadermazi et al., 2007]. Starting with a 1:1 molar ratio of the reactants in THF, a puffy white precipitate was obtained. By recrystallization in an aqueous solution, pale-yellow crystals were obtained. A solution of Co(NO3)2.6H2O (196 mg, 0.5 mmol) in water (15 ml) was added to an aqueous solution of (pnH2)2(btc).2H2O (253 mg, 1.0 mmol) in water (15 ml) in a 1:2 molar ratio. Colorless crystals suitable for X-ray characterization were obtained after a few days at room temperature.

Refinement top

The hydrogen atoms of the NH~3~ group and water molecules were found in the difference Fourier map. The H(C) atom positions were calculated. All hydrogen atoms were refined in isotropic approximation in riding model with with the Uĩso~(H) parameters equal to 1.2 U~eq~(Ci), 1.2 U~eq~(Oi) and 1.2 U~eq~(Ni) where U(Ci), U(Oi) and U(Ni) are respectively the equivalent thermal parameters of the carbon, oxygen and nitrigen atoms to which corresponding H atoms are bonded. Water molecule H(6 A)—O(6)—H(6B) has a total ocuppancy equal to 1/2 and is disordered by two positions, H(6B) atom is common for two positions. There is pseudo-symmetry in the crystal (space group Imma). However, the cation and water molecule are strongly disordered in the suggested Imma setting. One of the carbonyl O atoms is also disordered in Imma by two positions. Our attempt to solve the disordered structure in Imma group did not lead to acceptable R1 and wR2 values. The space group Ima2 is non-centrosymmetric so the Flack parameter can be calculated. The crystal is a racemic twin, so we used the TWIN instruction to refine the structure. In this case the Flack parameter is equal to the twin parameter of TWIN refinement (BASF). A total of 1206 Friedel pairs was measured.

Structure description top

We have reported cases in which proton transfer from benzene-1,2,4,5-tetracarboxylic acid (btcH4) to propane-1,3-diamine (pn), piperazine (pipz) and 1,10-phenanthroline (phen), resulted in the formation of novel self assembled (pnH2)2(btc).2H2O (Aghabozorg, Ghadermazi et al., 2007), (pipzH2)2(btc).6.2H2O (Aghabozorg, Manteghi, Ghadermazi 2007) and (phenH)4(btcH3)2(btcH2) (Aghabozorg, Ghadermazi & Attar Gharamaleki, 2006) systems, respectively. The resulting compounds, with some remaining sites as electron donors, can coordinate to metal ions (Aghabozorg, Ghasemikhah, Ghadermazi et al., 2006; Aghabozorg, Ghasemikhah, Soleimannejad et al., 2006). For the crystal structures of related complexes, see: Aghabozorg, Bahrami, et al., (2007); Aghabozorg, Zabihi et al., 2006; Aghabozorg, Attar Gharamaleki et al., 2007).

Here, we report a new polymeric compound obtained from reaction of (pnH2)2(btc).2H2O with cobalt(II) nitrate. The crystal structure of the title polymeric compound is shown in Fig. 1. The negative charge of the anionic complex is neutralized by dicationic propane-1,3-diammonium ions. The Co2+ atom is situated on a crystallographic twofold rotation axis.

Co2+ is six-coordinated by four (btc)4– groups and two coordinated water molecules, i.e. each (btc)4– fragments coordinates through one O atom of the (COO)- fragments, which also act as bridging ligands between other Co2+ ions. O5 and O5a atoms of two coordinated water molecules occupy the axial positions, while four O atoms of (btc)4– fragments form the equatorial plane. The axial bond is slightly longer than the equatorial bond lengths. The O5iii—Co1—O5 bond angle is slightly deviated from linearity. The coordination around Co2+ is distorted octahedral.

A considerable feature of the compound (Sharif et al., 2007) is the presence of C—H···π stacking interactions between C—H groups of (pnH2)2+ cations and aromatic rings of (btc)4– fragments (Fig. 2). The most important feature of the crystal structure is the presence of a large number of O—H···O, N—H···O and C—H···O hydrogen bonds between (pnH2)2+ and [Co(H2O)2(btc)]2– fragments and uncoordinated water molecules with D···A distances ranging from 2.679 (1) Å to 3.251 (2) Å. Hydrogen bonding, ion pairing, C—H···π stacking and van der Waals forces are effective in the stabilization of the crystal structure, resulting in the formation of an interesting supramolecular structure (Fig. 3).

For related literature, see: Aghabozorg, Attar Gharamaleki et al. (2007); Aghabozorg, Bahrami et al. (2007); Aghabozorg, Ghadermazi & Attar Gharamaleki (2006); Aghabozorg, Ghadermazi et al. (2007); Aghabozorg, Ghasemikhah, Ghadermazi et al. (2006); Aghabozorg, Ghasemikhah, Soleimannejad et al. (2006); Aghabozorg, Manteghi & Ghadermazi (2007); Aghabozorg, Zabihi et al. (2006); Sharif et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL Bruker, 2005); software used to prepare material for publication: SHELXTL Bruker, 2005).

Figures top
[Figure 1] Fig. 1. Full environment of Co1 center for compound (I). Atoms Co1C and Co1F belong to a twofold axis. Co Atoms labeled with A—G are obtained by the following symmetry operations: A: x, 1.5 - y, -1/2 + z B: 1 - x, 1/2 + y, -1/2 + z C: 1 - x, 1 - y, z D: 1.5 - x, y, z E: 1.5 - x, 1.5 - y, -1/2 + z F: -1/2 + x, -1/2 + y, -1/2 + z G: -1/2 + x, 1 - y, z.
[Figure 2] Fig. 2. The C—H···π distances (measured to the centre of phenyl ring) are 2.61 Å (1/2 + x, 1/2 + y, 1/2 + z) and 2.98 Å (1/2 + x,-1/2 + y, 1/2 + z) and the C–H···π angles are 141° and 137°, respectively.
[Figure 3] Fig. 3. Crystal packing of the title compound viewed along a crystal axis. Hydrogen atoms are omitted for clarity.
Poly[propane-1,3-diammonium [diaqua(µ4-4-benzene-1,2,4,5-tetracarboxylato)cobaltate(II)] hemihydrate] top
Crystal data top
(C3H12N2)[Co(C10H2O8)(H2O)2]·0.5H2OF(000) = 888
Mr = 430.23Dx = 1.702 Mg m3
Orthorhombic, Ima2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: I 2 -2aCell parameters from 6735 reflections
a = 16.4011 (3) Åθ = 2.5–46.7°
b = 7.1786 (1) ŵ = 1.09 mm1
c = 14.2586 (2) ÅT = 100 K
V = 1678.76 (5) Å3Prism, colourless
Z = 40.22 × 0.18 × 0.13 mm
Data collection top
Bruker APEXII CCD
diffractometer
2526 independent reflections
Radiation source: fine-focus sealed tube2479 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
ω scansθmax = 30.0°, θmin = 3.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 2323
Tmin = 0.796, Tmax = 0.872k = 1010
19141 measured reflectionsl = 2020
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.022H-atom parameters constrained
wR(F2) = 0.066 w = 1/[σ2(Fo2) + (0.05P)2 + P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.004
2526 reflectionsΔρmax = 0.81 e Å3
134 parametersΔρmin = 0.35 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.375 (11)
Crystal data top
(C3H12N2)[Co(C10H2O8)(H2O)2]·0.5H2OV = 1678.76 (5) Å3
Mr = 430.23Z = 4
Orthorhombic, Ima2Mo Kα radiation
a = 16.4011 (3) ŵ = 1.09 mm1
b = 7.1786 (1) ÅT = 100 K
c = 14.2586 (2) Å0.22 × 0.18 × 0.13 mm
Data collection top
Bruker APEXII CCD
diffractometer
2526 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
2479 reflections with I > 2σ(I)
Tmin = 0.796, Tmax = 0.872Rint = 0.026
19141 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.022H-atom parameters constrained
wR(F2) = 0.066Δρmax = 0.81 e Å3
S = 1.00Δρmin = 0.35 e Å3
2526 reflectionsAbsolute structure: Flack (1983)
134 parametersAbsolute structure parameter: 0.375 (11)
1 restraint
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*/UeqOcc. (<1)
Co10.50000.50000.82749 (2)0.00585 (4)
O10.59187 (6)0.93889 (14)1.23336 (6)0.01174 (18)
O20.54019 (5)0.69011 (13)1.15830 (6)0.01297 (17)
O30.56026 (5)0.86184 (13)0.96344 (7)0.01294 (16)
O40.58410 (6)0.55896 (14)0.93363 (6)0.01095 (17)
C10.75000.8092 (3)1.17061 (12)0.0095 (3)
H1A0.75000.84831.23430.011*
C20.67589 (7)0.78092 (16)1.12452 (9)0.0090 (2)
C30.67626 (7)0.72442 (17)1.03074 (8)0.0083 (2)
C40.75000.6944 (2)0.98435 (12)0.0095 (3)
H4A0.75000.65350.92100.011*
C50.59580 (7)0.80529 (17)1.17606 (8)0.0093 (2)
C60.59980 (7)0.71361 (17)0.97228 (8)0.0090 (2)
O50.45721 (5)0.77721 (11)0.82396 (8)0.01252 (15)
H5B0.47700.81920.87810.015*
H5A0.48060.82550.77320.015*
N10.40163 (6)0.73402 (16)0.54638 (8)0.0136 (2)
H1B0.44600.74220.58440.020*
H1C0.40440.82410.50160.020*
H1D0.40060.62000.51850.020*
C70.32604 (8)0.75991 (19)0.60320 (9)0.0136 (2)
H7A0.32480.88810.62880.016*
H7B0.32640.67180.65660.016*
C80.25000.7265 (3)0.54340 (14)0.0133 (3)
H8A0.25000.59710.51950.016*
H8B0.25000.81230.48900.016*
O60.2991 (5)0.9781 (12)0.8219 (7)0.071 (2)0.25
H6A0.33330.88450.81050.085*0.25
H6B0.25000.93200.81010.085*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.00543 (8)0.00700 (8)0.00512 (8)0.00108 (6)0.0000.000
O10.0107 (4)0.0125 (4)0.0120 (4)0.0006 (4)0.0035 (3)0.0034 (3)
O20.0105 (4)0.0155 (4)0.0129 (4)0.0035 (3)0.0009 (3)0.0023 (3)
O30.0122 (3)0.0118 (4)0.0149 (4)0.0024 (3)0.0036 (3)0.0017 (3)
O40.0107 (4)0.0114 (4)0.0107 (4)0.0002 (3)0.0025 (3)0.0008 (3)
C10.0094 (7)0.0114 (6)0.0077 (7)0.0000.0000.0018 (6)
C20.0103 (5)0.0077 (5)0.0091 (5)0.0004 (4)0.0010 (4)0.0016 (4)
C30.0061 (4)0.0094 (5)0.0095 (5)0.0000 (4)0.0000 (4)0.0007 (4)
C40.0095 (7)0.0090 (6)0.0099 (8)0.0000.0000.0009 (6)
C50.0084 (5)0.0106 (5)0.0089 (5)0.0006 (4)0.0000 (4)0.0009 (4)
C60.0080 (4)0.0114 (5)0.0078 (5)0.0011 (4)0.0011 (4)0.0003 (4)
O50.0144 (3)0.0129 (3)0.0103 (3)0.0005 (3)0.0004 (4)0.0000 (3)
N10.0095 (4)0.0143 (5)0.0170 (5)0.0001 (4)0.0009 (4)0.0029 (4)
C70.0121 (5)0.0122 (5)0.0166 (6)0.0004 (4)0.0004 (4)0.0010 (5)
C80.0099 (6)0.0132 (7)0.0169 (7)0.0000.0000.0012 (6)
O60.056 (3)0.120 (6)0.036 (3)0.056 (4)0.014 (4)0.001 (4)
Geometric parameters (Å, º) top
Co1—O1i2.0650 (9)C4—H4A0.9500
Co1—O42.0910 (9)O5—H5B0.8899
Co1—O52.1107 (8)O5—H5A0.8901
O1—C51.2615 (16)N1—C71.4926 (16)
O1—Co1ii2.0650 (9)N1—H1B0.9100
O2—C51.2569 (15)N1—H1C0.9100
O3—C61.2525 (15)N1—H1D0.9100
O4—C61.2659 (16)C7—C81.5297 (17)
C1—C21.3967 (15)C7—H7A0.9900
C1—C2iii1.3967 (15)C7—H7B0.9900
C1—H1A0.9500C8—C7iv1.5297 (17)
C2—C31.3973 (14)C8—H8A0.9900
C2—C51.5153 (17)C8—H8B0.9900
C3—C41.3952 (14)O6—O6iv1.612 (15)
C3—C61.5077 (17)O6—H6A0.8900
C4—C3iii1.3952 (14)O6—H6B0.8873
O1i—Co1—O1v98.92 (5)O1—C5—C2116.50 (11)
O1i—Co1—O4174.14 (4)O3—C6—O4126.57 (11)
O1v—Co1—O486.91 (3)O3—C6—C3116.27 (11)
O4—Co1—O4vi87.26 (5)O4—C6—C3117.07 (11)
O1i—Co1—O5vi91.54 (4)Co1—O5—H5B100.2
O1v—Co1—O5vi86.68 (4)Co1—O5—H5A104.1
O4—Co1—O5vi89.36 (4)H5B—O5—H5A114.6
O4vi—Co1—O5vi92.62 (4)C7—N1—H1B109.5
O1v—Co1—O591.54 (4)C7—N1—H1C109.5
O4—Co1—O592.62 (4)H1B—N1—H1C109.5
O4vi—Co1—O589.36 (4)C7—N1—H1D109.5
O5vi—Co1—O5177.26 (6)H1B—N1—H1D109.5
C5—O1—Co1ii128.29 (8)H1C—N1—H1D109.5
C6—O4—Co1128.82 (8)N1—C7—C8110.80 (11)
C2—C1—C2iii120.99 (16)N1—C7—H7A109.5
C2—C1—H1A119.5C8—C7—H7A109.5
C2iii—C1—H1A119.5N1—C7—H7B109.5
C1—C2—C3119.25 (13)C8—C7—H7B109.5
C1—C2—C5120.62 (11)H7A—C7—H7B108.1
C3—C2—C5120.10 (12)C7—C8—C7iv109.24 (15)
C4—C3—C2120.15 (13)C7—C8—H8A109.8
C4—C3—C6116.80 (11)C7iv—C8—H8A109.8
C2—C3—C6122.71 (12)C7—C8—H8B109.8
C3—C4—C3iii120.18 (15)C7iv—C8—H8B109.8
C3—C4—H4A119.9H8A—C8—H8B108.3
C3iii—C4—H4A119.9O6iv—O6—H6A129.1
O2—C5—O1126.41 (11)H6A—O6—H6B104.9
O2—C5—C2117.09 (11)
O1v—Co1—O4—C688.68 (11)Co1ii—O1—C5—C2172.14 (8)
O4vi—Co1—O4—C691.95 (11)C1—C2—C5—O2140.38 (14)
O5vi—Co1—O4—C6175.39 (11)C3—C2—C5—O237.76 (15)
O5—Co1—O4—C62.72 (11)C1—C2—C5—O139.04 (18)
C2iii—C1—C2—C30.4 (2)C3—C2—C5—O1142.82 (11)
C2iii—C1—C2—C5177.80 (11)Co1—O4—C6—O310.12 (19)
C1—C2—C3—C40.84 (16)Co1—O4—C6—C3166.26 (8)
C5—C2—C3—C4177.32 (13)C4—C3—C6—O3114.56 (14)
C1—C2—C3—C6172.23 (14)C2—C3—C6—O358.73 (15)
C5—C2—C3—C69.60 (15)C4—C3—C6—O462.21 (17)
C2—C3—C4—C3iii1.3 (2)C2—C3—C6—O4124.50 (12)
C6—C3—C4—C3iii172.13 (10)N1—C7—C8—C7iv178.35 (9)
Co1ii—O1—C5—O27.22 (19)
Symmetry codes: (i) x+1, y1/2, z1/2; (ii) x, y+3/2, z+1/2; (iii) x+3/2, y, z; (iv) x+1/2, y, z; (v) x, y+3/2, z1/2; (vi) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5B···O30.891.852.680 (1)153
O5—H5A···O2v0.891.912.737 (1)154
N1—H1B···O2v0.911.932.831 (1)168
N1—H1C···O4vii0.911.952.843 (2)166
N1—H1D···O3i0.912.112.988 (2)161
C7—H7B···Cgviii0.992.983.767 (2)137
C8—H8B···Cgix0.992.613.439 (2)141
Symmetry codes: (i) x+1, y1/2, z1/2; (v) x, y+3/2, z1/2; (vii) x+1, y+1/2, z1/2; (viii) x+1/2, y1/2, z+1/2; (ix) x+1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula(C3H12N2)[Co(C10H2O8)(H2O)2]·0.5H2O
Mr430.23
Crystal system, space groupOrthorhombic, Ima2
Temperature (K)100
a, b, c (Å)16.4011 (3), 7.1786 (1), 14.2586 (2)
V3)1678.76 (5)
Z4
Radiation typeMo Kα
µ (mm1)1.09
Crystal size (mm)0.22 × 0.18 × 0.13
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.796, 0.872
No. of measured, independent and
observed [I > 2σ(I)] reflections
19141, 2526, 2479
Rint0.026
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.022, 0.066, 1.00
No. of reflections2526
No. of parameters134
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.81, 0.35
Absolute structureFlack (1983)
Absolute structure parameter0.375 (11)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL Bruker, 2005).

Selected geometric parameters (Å, º) top
Co1—O1i2.0650 (9)Co1—O52.1107 (8)
Co1—O42.0910 (9)
O1i—Co1—O4174.14 (4)O5ii—Co1—O5177.26 (6)
Symmetry codes: (i) x+1, y1/2, z1/2; (ii) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5B···O30.891.852.680 (1)153
O5—H5A···O2iii0.891.912.737 (1)154
N1—H1B···O2iii0.911.932.831 (1)168
N1—H1C···O4iv0.911.952.843 (2)166
N1—H1D···O3i0.912.112.988 (2)161
C7—H7B···Cgv0.992.983.767 (2)137
C8—H8B···Cgvi0.992.613.439 (2)141
Symmetry codes: (i) x+1, y1/2, z1/2; (iii) x, y+3/2, z1/2; (iv) x+1, y+1/2, z1/2; (v) x+1/2, y1/2, z+1/2; (vi) x+1/2, y+1/2, z+1/2.
 

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