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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): m1234–m1235.
Published online 2008 September 6. doi:  10.1107/S1600536808027700
PMCID: PMC2959312

Creatininium bis­(pyridine-2,6-dicarboxyl­ato)chromate(III) pyridine-2,6-dicarboxylic acid hexa­hydrate

Abstract

The title compound, (C4H8N3O)[Cr(C7H3NO4)2]·C7H5NO4·6H2O, was obtained by the reaction of Cr(NO3)3·9H2O with pyridine-2,6-dicarboxylic acid (pydcH2) and creatinine (creat) in aqueous solution (molar ratio 1:2:2). The cation is a protonated creatinine (creatH+) while the anion is a bis-pydc2− CrIII complex. The CrIII is coordinated by four oxygen and two nitro­gen atoms of two (pydc)2– groups and has a disorted octa­hedral coordination environment. The structure also contains a neutral mol­ecule of pydcH2 that is hydrogen bonded to the creatH+ and six mol­ecules of water. Extensive inter­molecular inter­actions, including seventeen classical hydrogen bonds, two weak C—H(...)O bonds, and C—O(...)π stacking inter­actions, with O(...)centroid distances of 3.211 (13) and 3.300 (12) Å, connect the various components in the crystal structure.

Related literature

For a recent review on proton-transfer compounds and their structures, see: Aghabozorg, Manteghi et al. (2008 [triangle]). For related creatininium structures, see: Aghabozorg, Ramezanipour et al. (2008 [triangle]); Moghimi et al. (2004 [triangle], 2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1234-scheme1.jpg

Experimental

Crystal data

  • (C4H8N3O)[Cr(C7H3NO4)2]·C7H5NO4·6H2O
  • M r = 771.56
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1234-efi1.jpg
  • a = 9.0860 (5) Å
  • b = 13.6274 (8) Å
  • c = 14.7301 (8) Å
  • α = 65.481 (2)°
  • β = 74.685 (2)°
  • γ = 77.644 (2)°
  • V = 1589.10 (15) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.46 mm−1
  • T = 90 (2) K
  • 0.33 × 0.32 × 0.10 mm

Data collection

  • Bruker SMART APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.864, T max = 0.956
  • 20278 measured reflections
  • 7266 independent reflections
  • 6654 reflections with I > 2σ(I)
  • R int = 0.019

Refinement

  • R[F 2 > 2σ(F 2)] = 0.028
  • wR(F 2) = 0.077
  • S = 1.01
  • 7266 reflections
  • 584 parameters
  • All H-atom parameters refined
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808027700/sj2533sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027700/sj2533Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank Tarbiat Moallem University for financial support and the University of California, Davis for the purchase of the X-ray diffractometer.

supplementary crystallographic information

Comment

We have previously reported several structures that contain creatinine, pyridine-2,6-dicarboxylic acid and various metals such as: (creatH)(pydcH).H2O (Moghimi et al., 2004), (creatH)2[Bi(pydc)2]2.4H2O (Moghimi et al., 2005) and (creatH)[Zn(pydc)(pydcH)]. 4H2O (Aghabozorg, Ramezanipour et al., 2008). For more details and related literature see our recent review article (Aghabozorg, Manteghi et al., 2008).

The asymmetric unit of the title compound Fig. 1, contains a [Cr(pydc)2]- anion, a (creatH)+ cation, a pydcH2 molecule and six uncoordinated water molecules. In the anions, CrIII has a N2O4 donor set with normal distances and angles (Table 1). The two (pydc)2– planes form a dihedral angle of 89.64 (1)°, and thus are virtually perpendicular to each other.

As depicted in Fig. 2, the creatininium ion is evidently strongly associated with the neutral molecule of pydcH2 through two N—H···O hydrogen bonds and the two units are bridged by one of the water molecules. There are also two rather strong hydrogen bonds between the two carboxylic acid OH groups of the pydcH2 and molecules of water. The relevant O···O distances are 2.5382 (15) and 2.5720 (14)Å. This structural arrangement between cation and neutral pydcH2 markedly differs from the arrangement in the ion pair creatH+pydcH- previously reported in the structure of the creatH+pydcH- monohydrate (Moghimi et al., 2004). In the latter structure, only one intramolecular hydrogen bond is formed between one of the NH2 H atoms and the carboxylate group. The other NH2 H atom is hydrogen bonded to the molecule of water.

In addition to numerous strong hydrogen bonds, intermolecular interactions in the the title compound include weaker C—H···O interactions which link the anions together, shown in Fig. 3 and Table 2, as well as C—O···π stacking interactions between CO groups of carboxylate fragments and aromatic rings of (pydc)2– with O···centroid distances of 3.211 (13) and 3.300 (12) Å (Fig. 4).

Experimental

The reaction between pyridine-2,6-dicarboxylic acid (100 mg, 1 mmol) in 10 ml water, creatinine (creat) (110 mg, 1 mmol) in 20 ml water and chromium(III) nitrate nonahydrate (100 mg, 0.5 mmol) in 5 ml water at 2:2:1 molar ratio gave violet crystals after slow evaporation of the solvent at the room temperature.

Refinement

All H atoms were freely refined with isotropic thermal parameters.

Figures

Fig. 1.
A view of the asymmetric unit of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
Fig. 2.
Details of the hydrogen bonding between the creatininium cation, the neutral pydcH2 molecule and the uncoordinated water molecules. Symmetry codes: (i) x, 1 + y, z, (ii) 1 - x, 1 - y, -z.
Fig. 3.
One dimensional chains of [Cr(pydc)2]- anions that are generated by C–H···O hydrogen bonds.
Fig. 4.
C–O···π stacking interactions in the title compound. Distances are reported between O atoms and the centroid (Cg) of the N1/C2-C6 aromatic ring. Symmetry codes: (i) 1-x, -y, 1-z), (ii) (-x, -y, 1-z).

Crystal data

(C4H8N3O)[Cr(C7H3NO4)2]·C7H5NO4·6H2OZ = 2
Mr = 771.56F(000) = 798
Triclinic, P1Dx = 1.612 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.0860 (5) ÅCell parameters from 6379 reflections
b = 13.6274 (8) Åθ = 3.0–31.5°
c = 14.7301 (8) ŵ = 0.46 mm1
α = 65.481 (2)°T = 90 K
β = 74.685 (2)°Plate, violet
γ = 77.644 (2)°0.33 × 0.32 × 0.10 mm
V = 1589.10 (15) Å3

Data collection

Bruker SMART APEXII diffractometer7266 independent reflections
Radiation source: fine-focus sealed tube6654 reflections with I > 2σ(I)
graphiteRint = 0.019
Detector resolution: 8.3 pixels mm-1θmax = 27.5°, θmin = 2.7°
ω scansh = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)k = −17→17
Tmin = 0.864, Tmax = 0.956l = −19→19
20278 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077All H-atom parameters refined
S = 1.02w = 1/[σ2(Fo2) + (0.0385P)2 + 0.9325P] where P = (Fo2 + 2Fc2)/3
7266 reflections(Δ/σ)max = 0.001
584 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = −0.46 e Å3

Special details

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)

xyzUiso*/Ueq
Cr10.25265 (2)0.216209 (16)0.359634 (15)0.01061 (6)
O10.36533 (10)0.23292 (7)0.45071 (7)0.01405 (18)
O20.46030 (11)0.14296 (8)0.59416 (7)0.0175 (2)
O30.15065 (11)0.14097 (8)0.30655 (7)0.01496 (19)
O40.07696 (12)−0.01935 (8)0.33737 (8)0.0200 (2)
O50.43892 (10)0.22188 (7)0.25150 (7)0.01432 (19)
O60.55182 (11)0.32381 (8)0.09398 (7)0.0181 (2)
O70.05282 (10)0.26969 (7)0.43082 (7)0.01383 (18)
O8−0.14469 (11)0.40222 (8)0.41140 (8)0.0189 (2)
N10.26631 (12)0.06706 (9)0.46327 (8)0.0116 (2)
N20.21136 (12)0.36451 (9)0.25887 (8)0.0120 (2)
C10.38970 (14)0.14811 (10)0.53165 (10)0.0130 (2)
C20.32378 (14)0.04896 (10)0.54427 (10)0.0126 (2)
C30.31731 (15)−0.05060 (11)0.62527 (10)0.0154 (3)
H30.3540 (19)−0.0619 (13)0.6818 (13)0.016 (4)*
C40.25291 (15)−0.13028 (11)0.61755 (10)0.0166 (3)
H40.2463 (19)−0.1981 (14)0.6707 (13)0.017 (4)*
C50.19581 (15)−0.11032 (11)0.53165 (11)0.0156 (3)
H50.150 (2)−0.1614 (14)0.5244 (13)0.020 (4)*
C60.20238 (14)−0.00750 (10)0.45504 (10)0.0131 (2)
C70.13731 (14)0.03755 (11)0.35899 (10)0.0140 (2)
C80.44766 (15)0.30926 (10)0.16929 (10)0.0133 (2)
C90.31394 (14)0.39718 (10)0.17162 (10)0.0128 (2)
C100.28865 (16)0.49990 (11)0.09810 (10)0.0154 (3)
H100.357 (2)0.5255 (15)0.0365 (14)0.023 (4)*
C110.15425 (16)0.56585 (11)0.11809 (10)0.0164 (3)
H110.135 (2)0.6360 (15)0.0687 (14)0.023 (4)*
C120.04727 (15)0.52912 (11)0.20890 (10)0.0152 (3)
H12−0.0436 (19)0.5732 (14)0.2231 (12)0.015 (4)*
C130.08062 (14)0.42558 (10)0.27889 (10)0.0127 (2)
C14−0.01527 (15)0.36454 (10)0.38121 (10)0.0134 (2)
O130.05039 (12)1.18680 (8)−0.06791 (8)0.0204 (2)
N40.39073 (15)0.87378 (10)0.02195 (10)0.0175 (2)
H4A0.476 (2)0.8454 (16)0.0006 (15)0.029 (5)*
H4B0.340 (2)0.8382 (16)0.0802 (16)0.028 (5)*
N50.19415 (13)1.02123 (9)−0.00184 (9)0.0156 (2)
H5A0.140 (2)0.9944 (16)0.0570 (16)0.032 (5)*
N60.39959 (13)1.03426 (9)−0.12569 (9)0.0156 (2)
C220.30056 (16)1.13631 (11)−0.16289 (11)0.0172 (3)
H22A0.350 (2)1.1955 (15)−0.1755 (14)0.024 (4)*
H22B0.2690 (19)1.1442 (13)−0.2225 (13)0.015 (4)*
C230.54951 (16)1.00844 (13)−0.18301 (11)0.0193 (3)
H23A0.540 (3)0.9830 (19)−0.2282 (19)0.051 (7)*
H23B0.617 (3)0.959 (2)−0.1406 (19)0.055 (7)*
H23C0.599 (3)1.070 (2)−0.217 (2)0.065 (8)*
C240.33392 (15)0.97084 (11)−0.03381 (10)0.0145 (2)
C250.16432 (16)1.12269 (11)−0.07475 (10)0.0161 (3)
O90.22431 (12)0.75720 (8)0.21745 (8)0.0222 (2)
O100.16856 (11)0.60735 (8)0.35557 (7)0.0185 (2)
H10A0.080 (3)0.6511 (19)0.3638 (17)0.045 (6)*
O110.69061 (11)0.75755 (8)−0.01882 (8)0.0204 (2)
O120.86113 (11)0.60775 (8)0.00786 (8)0.0185 (2)
H12A0.915 (3)0.649 (2)−0.0534 (19)0.051 (7)*
N30.50100 (13)0.65317 (9)0.16037 (9)0.0143 (2)
C150.25904 (15)0.66364 (11)0.27266 (10)0.0158 (3)
C160.41037 (15)0.59999 (11)0.24827 (10)0.0149 (3)
C170.44864 (16)0.49323 (11)0.31185 (10)0.0167 (3)
H170.381 (2)0.4595 (15)0.3761 (14)0.024 (4)*
C180.58702 (16)0.43822 (11)0.28135 (11)0.0181 (3)
H180.613 (2)0.3676 (16)0.3202 (14)0.023 (4)*
C190.68190 (16)0.49118 (11)0.18923 (11)0.0167 (3)
H190.777 (2)0.4580 (14)0.1653 (13)0.021 (4)*
C200.63432 (15)0.59888 (11)0.13218 (10)0.0145 (2)
C210.73088 (15)0.66371 (11)0.03255 (10)0.0152 (3)
O14−0.28792 (14)0.61850 (10)0.36097 (10)0.0268 (2)
H14A−0.377 (3)0.6268 (19)0.3838 (18)0.048 (7)*
H14B−0.258 (3)0.553 (2)0.3801 (17)0.041 (6)*
O15−0.08716 (12)0.72137 (9)0.38192 (8)0.0220 (2)
H15A−0.160 (3)0.6886 (18)0.3832 (17)0.040 (6)*
H15B−0.098 (3)0.7271 (18)0.4335 (18)0.039 (6)*
O160.00515 (12)−0.05810 (9)0.18249 (8)0.0188 (2)
H16A0.008 (3)−0.0312 (19)0.2190 (18)0.041 (6)*
H16B0.043 (3)−0.122 (2)0.2076 (18)0.049 (7)*
O17−0.02251 (12)0.28295 (9)0.16386 (8)0.0189 (2)
H17A−0.076 (3)0.2496 (18)0.1493 (16)0.039 (6)*
H17B0.029 (3)0.2388 (19)0.2012 (18)0.041 (6)*
O180.59381 (13)0.31757 (10)0.57788 (9)0.0256 (2)
H18A0.571 (3)0.2635 (19)0.5733 (16)0.040 (6)*
H18B0.673 (3)0.3345 (19)0.5322 (19)0.048 (7)*
O190.81371 (13)0.17421 (9)0.11655 (9)0.0220 (2)
H19A0.731 (3)0.215 (2)0.1020 (18)0.050 (7)*
H19B0.867 (3)0.1690 (18)0.0646 (18)0.043 (6)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cr10.01120 (10)0.00907 (10)0.00929 (10)−0.00114 (7)−0.00217 (7)−0.00125 (8)
O10.0153 (4)0.0122 (4)0.0137 (4)−0.0024 (3)−0.0039 (3)−0.0029 (4)
O20.0175 (5)0.0198 (5)0.0164 (5)−0.0028 (4)−0.0066 (4)−0.0059 (4)
O30.0158 (4)0.0152 (4)0.0136 (4)−0.0018 (3)−0.0041 (3)−0.0045 (4)
O40.0214 (5)0.0206 (5)0.0232 (5)−0.0033 (4)−0.0063 (4)−0.0118 (4)
O50.0134 (4)0.0126 (4)0.0127 (4)−0.0005 (3)−0.0017 (3)−0.0016 (4)
O60.0162 (5)0.0165 (5)0.0146 (5)−0.0017 (4)0.0017 (4)−0.0023 (4)
O70.0140 (4)0.0125 (4)0.0125 (4)−0.0016 (3)−0.0020 (3)−0.0026 (4)
O80.0144 (5)0.0185 (5)0.0191 (5)0.0005 (4)−0.0003 (4)−0.0055 (4)
N10.0101 (5)0.0106 (5)0.0120 (5)−0.0004 (4)−0.0012 (4)−0.0034 (4)
N20.0126 (5)0.0112 (5)0.0116 (5)−0.0019 (4)−0.0032 (4)−0.0030 (4)
C10.0110 (6)0.0134 (6)0.0124 (6)−0.0004 (5)−0.0004 (4)−0.0044 (5)
C20.0092 (5)0.0133 (6)0.0131 (6)0.0004 (4)−0.0014 (4)−0.0043 (5)
C30.0130 (6)0.0161 (6)0.0128 (6)0.0011 (5)−0.0018 (5)−0.0029 (5)
C40.0145 (6)0.0107 (6)0.0163 (6)0.0001 (5)0.0008 (5)−0.0003 (5)
C50.0120 (6)0.0117 (6)0.0204 (7)−0.0015 (5)0.0006 (5)−0.0057 (5)
C60.0097 (5)0.0131 (6)0.0154 (6)−0.0002 (4)−0.0004 (5)−0.0061 (5)
C70.0109 (6)0.0161 (6)0.0144 (6)0.0006 (5)−0.0007 (5)−0.0072 (5)
C80.0137 (6)0.0120 (6)0.0134 (6)−0.0020 (5)−0.0040 (5)−0.0029 (5)
C90.0123 (6)0.0132 (6)0.0126 (6)−0.0029 (5)−0.0030 (5)−0.0036 (5)
C100.0161 (6)0.0142 (6)0.0129 (6)−0.0037 (5)−0.0024 (5)−0.0017 (5)
C110.0194 (7)0.0105 (6)0.0160 (6)−0.0018 (5)−0.0064 (5)−0.0002 (5)
C120.0151 (6)0.0132 (6)0.0170 (6)−0.0002 (5)−0.0049 (5)−0.0050 (5)
C130.0124 (6)0.0134 (6)0.0137 (6)−0.0023 (5)−0.0034 (5)−0.0056 (5)
C140.0143 (6)0.0134 (6)0.0133 (6)−0.0031 (5)−0.0030 (5)−0.0050 (5)
O130.0199 (5)0.0185 (5)0.0230 (5)0.0060 (4)−0.0071 (4)−0.0104 (4)
N40.0171 (6)0.0156 (6)0.0160 (6)0.0020 (5)−0.0035 (5)−0.0040 (5)
N50.0153 (5)0.0152 (5)0.0145 (6)0.0010 (4)−0.0026 (4)−0.0054 (5)
N60.0154 (5)0.0135 (5)0.0152 (5)0.0013 (4)−0.0033 (4)−0.0041 (4)
C220.0189 (7)0.0134 (6)0.0171 (6)0.0017 (5)−0.0046 (5)−0.0046 (5)
C230.0163 (7)0.0232 (7)0.0163 (7)0.0009 (5)−0.0020 (5)−0.0078 (6)
C240.0153 (6)0.0153 (6)0.0149 (6)−0.0005 (5)−0.0052 (5)−0.0071 (5)
C250.0187 (6)0.0158 (6)0.0168 (6)−0.0008 (5)−0.0065 (5)−0.0078 (5)
O90.0191 (5)0.0192 (5)0.0199 (5)0.0038 (4)−0.0009 (4)−0.0042 (4)
O100.0149 (5)0.0199 (5)0.0187 (5)−0.0026 (4)0.0000 (4)−0.0071 (4)
O110.0169 (5)0.0182 (5)0.0198 (5)0.0005 (4)−0.0032 (4)−0.0027 (4)
O120.0156 (5)0.0191 (5)0.0175 (5)0.0007 (4)−0.0008 (4)−0.0066 (4)
N30.0138 (5)0.0145 (5)0.0154 (5)−0.0008 (4)−0.0040 (4)−0.0062 (4)
C150.0154 (6)0.0177 (6)0.0151 (6)−0.0021 (5)−0.0036 (5)−0.0067 (5)
C160.0157 (6)0.0154 (6)0.0156 (6)−0.0021 (5)−0.0044 (5)−0.0070 (5)
C170.0184 (6)0.0154 (6)0.0163 (6)−0.0041 (5)−0.0037 (5)−0.0050 (5)
C180.0209 (7)0.0124 (6)0.0200 (7)−0.0008 (5)−0.0073 (5)−0.0038 (5)
C190.0156 (6)0.0155 (6)0.0206 (7)0.0006 (5)−0.0057 (5)−0.0084 (5)
C200.0148 (6)0.0151 (6)0.0155 (6)−0.0017 (5)−0.0048 (5)−0.0066 (5)
C210.0139 (6)0.0178 (6)0.0161 (6)−0.0014 (5)−0.0046 (5)−0.0077 (5)
O140.0180 (6)0.0181 (6)0.0398 (7)0.0000 (4)−0.0020 (5)−0.0100 (5)
O150.0191 (5)0.0293 (6)0.0188 (5)−0.0005 (4)−0.0025 (4)−0.0122 (5)
O160.0224 (5)0.0170 (5)0.0175 (5)0.0006 (4)−0.0048 (4)−0.0080 (4)
O170.0174 (5)0.0201 (5)0.0166 (5)0.0003 (4)−0.0054 (4)−0.0044 (4)
O180.0191 (5)0.0295 (6)0.0342 (6)−0.0083 (4)0.0033 (5)−0.0204 (5)
O190.0187 (5)0.0239 (5)0.0215 (5)0.0022 (4)−0.0059 (4)−0.0080 (4)

Geometric parameters (Å, °)

Cr1—N11.9733 (11)N5—C251.3782 (17)
Cr1—N21.9769 (11)N5—H5A0.85 (2)
Cr1—O51.9842 (9)N6—C241.3259 (17)
Cr1—O31.9942 (10)N6—C231.4581 (18)
Cr1—O11.9947 (9)N6—C221.4616 (17)
Cr1—O71.9974 (9)C22—C251.5171 (19)
O1—C11.3009 (15)C22—H22A0.938 (19)
O2—C11.2262 (16)C22—H22B0.952 (17)
O3—C71.3106 (16)C23—H23A0.90 (3)
O4—C71.2176 (17)C23—H23B0.95 (3)
O5—C81.2975 (15)C23—H23C0.92 (3)
O6—C81.2283 (16)O9—C151.2204 (17)
O7—C141.3039 (16)O10—C151.3107 (17)
O8—C141.2244 (16)O10—H10A0.91 (2)
N1—C61.3329 (17)O11—C211.2184 (17)
N1—C21.3366 (17)O12—C211.3157 (16)
N2—C131.3365 (17)O12—H12A0.91 (2)
N2—C91.3373 (16)N3—C201.3390 (17)
C1—C21.5160 (18)N3—C161.3391 (17)
C2—C31.3861 (18)C15—C161.5031 (18)
C3—C41.394 (2)C16—C171.3926 (19)
C3—H30.920 (17)C17—C181.386 (2)
C4—C51.395 (2)C17—H170.970 (18)
C4—H40.932 (17)C18—C191.393 (2)
C5—C61.3886 (18)C18—H180.909 (19)
C5—H50.934 (18)C19—C201.3942 (19)
C6—C71.5145 (18)C19—H190.935 (18)
C8—C91.5172 (18)C20—C211.5099 (19)
C9—C101.3859 (18)O14—H14A0.79 (3)
C10—C111.3949 (19)O14—H14B0.83 (2)
C10—H100.927 (19)O15—H15A0.86 (2)
C11—C121.3965 (19)O15—H15B0.77 (2)
C11—H110.944 (18)O16—H16A0.78 (2)
C12—C131.3858 (18)O16—H16B0.83 (3)
C12—H120.942 (17)O17—H17A0.85 (2)
C13—C141.5161 (18)O17—H17B0.79 (2)
O13—C251.2149 (17)O18—H18A0.84 (2)
N4—C241.3117 (18)O18—H18B0.84 (3)
N4—H4A0.83 (2)O19—H19A0.85 (3)
N4—H4B0.85 (2)O19—H19B0.81 (2)
N5—C241.3731 (17)
N1—Cr1—N2172.88 (4)N2—C13—C14110.86 (11)
N1—Cr1—O5106.16 (4)C12—C13—C14128.84 (12)
N2—Cr1—O579.39 (4)O8—C14—O7124.76 (12)
N1—Cr1—O378.84 (4)O8—C14—C13121.81 (12)
N2—Cr1—O396.78 (4)O7—C14—C13113.42 (11)
O5—Cr1—O391.39 (4)C24—N4—H4A120.6 (14)
N1—Cr1—O179.13 (4)C24—N4—H4B120.3 (13)
N2—Cr1—O1105.30 (4)H4A—N4—H4B119.1 (19)
O5—Cr1—O193.27 (4)C24—N5—C25110.51 (11)
O3—Cr1—O1157.91 (4)C24—N5—H5A123.0 (14)
N1—Cr1—O796.08 (4)C25—N5—H5A126.3 (14)
N2—Cr1—O778.42 (4)C24—N6—C23125.88 (12)
O5—Cr1—O7157.76 (4)C24—N6—C22110.40 (11)
O3—Cr1—O792.80 (4)C23—N6—C22123.72 (11)
O1—Cr1—O791.01 (4)N6—C22—C25102.34 (11)
C1—O1—Cr1117.31 (8)N6—C22—H22A110.6 (11)
C7—O3—Cr1117.92 (8)C25—C22—H22A111.4 (11)
C8—O5—Cr1117.46 (8)N6—C22—H22B111.1 (10)
C14—O7—Cr1117.96 (8)C25—C22—H22B110.6 (10)
C6—N1—C2123.01 (11)H22A—C22—H22B110.6 (15)
C6—N1—Cr1118.48 (9)N6—C23—H23A111.2 (15)
C2—N1—Cr1118.06 (9)N6—C23—H23B112.8 (15)
C13—N2—C9123.11 (11)H23A—C23—H23B110 (2)
C13—N2—Cr1118.99 (9)N6—C23—H23C109.5 (17)
C9—N2—Cr1117.84 (9)H23A—C23—H23C109 (2)
O2—C1—O1126.04 (12)H23B—C23—H23C104 (2)
O2—C1—C2120.05 (11)N4—C24—N6126.64 (13)
O1—C1—C2113.91 (11)N4—C24—N5122.86 (13)
N1—C2—C3120.18 (12)N6—C24—N5110.49 (11)
N1—C2—C1111.06 (11)O13—C25—N5125.75 (13)
C3—C2—C1128.76 (12)O13—C25—C22128.00 (13)
C2—C3—C4117.72 (12)N5—C25—C22106.25 (11)
C2—C3—H3119.9 (11)C15—O10—H10A107.6 (14)
C4—C3—H3122.4 (10)C21—O12—H12A110.0 (15)
C3—C4—C5121.20 (12)C20—N3—C16117.38 (11)
C3—C4—H4120.1 (10)O9—C15—O10124.43 (13)
C5—C4—H4118.7 (11)O9—C15—C16122.17 (12)
C6—C5—C4117.61 (12)O10—C15—C16113.34 (12)
C6—C5—H5118.9 (11)N3—C16—C17123.71 (12)
C4—C5—H5123.5 (11)N3—C16—C15114.63 (11)
N1—C6—C5120.24 (12)C17—C16—C15121.64 (12)
N1—C6—C7111.66 (11)C18—C17—C16118.11 (13)
C5—C6—C7128.04 (12)C18—C17—H17121.6 (11)
O4—C7—O3125.86 (12)C16—C17—H17120.3 (11)
O4—C7—C6121.13 (12)C17—C18—C19119.22 (13)
O3—C7—C6112.99 (11)C17—C18—H18119.9 (12)
O6—C8—O5125.49 (12)C19—C18—H18120.8 (12)
O6—C8—C9120.42 (11)C18—C19—C20118.15 (13)
O5—C8—C9114.09 (11)C18—C19—H19122.6 (11)
N2—C9—C10119.86 (12)C20—C19—H19119.2 (11)
N2—C9—C8111.14 (11)N3—C20—C19123.42 (12)
C10—C9—C8129.00 (12)N3—C20—C21114.59 (11)
C9—C10—C11118.03 (12)C19—C20—C21122.00 (12)
C9—C10—H10122.6 (11)O11—C21—O12124.35 (13)
C11—C10—H10119.4 (11)O11—C21—C20122.94 (12)
C10—C11—C12121.08 (12)O12—C21—C20112.71 (11)
C10—C11—H11118.9 (11)H14A—O14—H14B109 (2)
C12—C11—H11120.0 (11)H15A—O15—H15B110 (2)
C13—C12—C11117.60 (12)H16A—O16—H16B106 (2)
C13—C12—H12120.7 (10)H17A—O17—H17B108 (2)
C11—C12—H12121.7 (10)H18A—O18—H18B104 (2)
N2—C13—C12120.29 (12)H19A—O19—H19B108 (2)
N1—Cr1—O1—C1−2.46 (9)C5—C6—C7—O4−4.4 (2)
N2—Cr1—O1—C1171.81 (9)N1—C6—C7—O3−2.96 (15)
O5—Cr1—O1—C1−108.30 (9)C5—C6—C7—O3174.13 (12)
O3—Cr1—O1—C1−6.46 (16)Cr1—O5—C8—O6−176.91 (10)
O7—Cr1—O1—C193.54 (9)Cr1—O5—C8—C92.87 (14)
N1—Cr1—O3—C70.88 (9)C13—N2—C9—C101.76 (19)
N2—Cr1—O3—C7−173.43 (9)Cr1—N2—C9—C10179.04 (10)
O5—Cr1—O3—C7107.08 (9)C13—N2—C9—C8−177.99 (11)
O1—Cr1—O3—C74.89 (16)Cr1—N2—C9—C8−0.71 (14)
O7—Cr1—O3—C7−94.76 (9)O6—C8—C9—N2178.40 (12)
N1—Cr1—O5—C8172.87 (9)O5—C8—C9—N2−1.39 (16)
N2—Cr1—O5—C8−2.55 (9)O6—C8—C9—C10−1.3 (2)
O3—Cr1—O5—C894.09 (9)O5—C8—C9—C10178.89 (13)
O1—Cr1—O5—C8−107.51 (9)N2—C9—C10—C11−0.54 (19)
O7—Cr1—O5—C8−6.78 (16)C8—C9—C10—C11179.17 (12)
N1—Cr1—O7—C14−170.15 (9)C9—C10—C11—C12−0.8 (2)
N2—Cr1—O7—C145.26 (9)C10—C11—C12—C130.9 (2)
O5—Cr1—O7—C149.50 (16)C9—N2—C13—C12−1.60 (19)
O3—Cr1—O7—C14−91.09 (9)Cr1—N2—C13—C12−178.85 (9)
O1—Cr1—O7—C14110.67 (9)C9—N2—C13—C14177.15 (11)
O5—Cr1—N1—C6−90.96 (10)Cr1—N2—C13—C14−0.10 (14)
O3—Cr1—N1—C6−2.76 (9)C11—C12—C13—N20.21 (19)
O1—Cr1—N1—C6178.77 (10)C11—C12—C13—C14−178.29 (12)
O7—Cr1—N1—C688.91 (10)Cr1—O7—C14—O8172.16 (10)
O5—Cr1—N1—C296.49 (9)Cr1—O7—C14—C13−6.72 (14)
O3—Cr1—N1—C2−175.31 (10)N2—C13—C14—O8−174.56 (12)
O1—Cr1—N1—C26.22 (9)C12—C13—C14—O84.0 (2)
O7—Cr1—N1—C2−83.64 (9)N2—C13—C14—O74.35 (15)
O5—Cr1—N2—C13179.09 (10)C12—C13—C14—O7−177.04 (13)
O3—Cr1—N2—C1388.95 (10)C24—N6—C22—C251.04 (14)
O1—Cr1—N2—C13−90.40 (10)C23—N6—C22—C25−178.54 (12)
O7—Cr1—N2—C13−2.54 (9)C23—N6—C24—N4−0.3 (2)
O5—Cr1—N2—C91.70 (9)C22—N6—C24—N4−179.89 (13)
O3—Cr1—N2—C9−88.45 (9)C23—N6—C24—N5178.95 (12)
O1—Cr1—N2—C992.21 (9)C22—N6—C24—N5−0.61 (15)
O7—Cr1—N2—C9−179.93 (10)C25—N5—C24—N4179.15 (12)
Cr1—O1—C1—O2177.87 (10)C25—N5—C24—N6−0.15 (16)
Cr1—O1—C1—C2−1.13 (14)C24—N5—C25—O13−179.32 (13)
C6—N1—C2—C3−0.63 (19)C24—N5—C25—C220.81 (15)
Cr1—N1—C2—C3171.56 (9)N6—C22—C25—O13179.04 (13)
C6—N1—C2—C1179.57 (11)N6—C22—C25—N5−1.09 (14)
Cr1—N1—C2—C1−8.24 (13)C20—N3—C16—C171.25 (19)
O2—C1—C2—N1−173.12 (11)C20—N3—C16—C15−176.95 (11)
O1—C1—C2—N15.95 (15)O9—C15—C16—N3−1.70 (19)
O2—C1—C2—C37.1 (2)O10—C15—C16—N3175.76 (11)
O1—C1—C2—C3−173.83 (12)O9—C15—C16—C17−179.95 (13)
N1—C2—C3—C41.51 (19)O10—C15—C16—C17−2.48 (18)
C1—C2—C3—C4−178.72 (12)N3—C16—C17—C18−1.4 (2)
C2—C3—C4—C5−0.50 (19)C15—C16—C17—C18176.71 (12)
C3—C4—C5—C6−1.35 (19)C16—C17—C18—C190.1 (2)
C2—N1—C6—C5−1.34 (19)C17—C18—C19—C201.2 (2)
Cr1—N1—C6—C5−173.49 (9)C16—N3—C20—C190.16 (19)
C2—N1—C6—C7176.01 (11)C16—N3—C20—C21−179.88 (11)
Cr1—N1—C6—C73.86 (14)C18—C19—C20—N3−1.4 (2)
C4—C5—C6—N12.27 (19)C18—C19—C20—C21178.67 (12)
C4—C5—C6—C7−174.60 (12)N3—C20—C21—O11−0.66 (19)
Cr1—O3—C7—O4179.27 (10)C19—C20—C21—O11179.30 (13)
Cr1—O3—C7—C60.84 (13)N3—C20—C21—O12179.64 (11)
N1—C6—C7—O4178.53 (12)C19—C20—C21—O12−0.40 (18)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N4—H4A···O110.83 (2)2.08 (2)2.8934 (16)167.3 (19)
N4—H4B···O90.85 (2)1.98 (2)2.8343 (16)178.5 (8)
O10—H10A···O150.91 (2)1.63 (2)2.5382 (15)176 (2)
O14—H14B···O80.83 (2)2.01 (2)2.8255 (16)169 (2)
O15—H15A···O140.86 (2)1.82 (2)2.6718 (17)168 (2)
O16—H16A···O40.78 (2)2.07 (2)2.8006 (15)156 (2)
O17—H17B···O30.79 (2)1.99 (2)2.7758 (14)172 (2)
O18—H18A···O20.84 (2)1.98 (2)2.7927 (15)162 (2)
O19—H19A···O60.85 (3)1.95 (3)2.7763 (15)164 (2)
N5—H5A···O16i0.85 (2)1.87 (2)2.7175 (16)175 (2)
O12—H12A···O17ii0.91 (2)1.66 (3)2.5720 (14)176 (2)
O14—H14A···O18iii0.79 (3)1.98 (3)2.7546 (17)167 (2)
O15—H15B···O7iii0.77 (2)2.16 (2)2.9105 (15)162 (2)
O16—H16B···O9iv0.83 (3)2.05 (3)2.8083 (15)152 (2)
O17—H17A···O19v0.85 (2)1.84 (2)2.6916 (16)178 (2)
O18—H18B···O8vi0.84 (3)2.12 (3)2.9558 (15)171 (2)
O19—H19B···O13vii0.81 (2)2.17 (2)2.9531 (16)162 (2)
C5—H5···O7viii0.94 (2)2.392 (19)3.251 (2)152.2 (15)
C10—H10···O6ii0.929 (19)2.283 (19)3.0919 (17)145.4 (18)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2533).

References

  • Aghabozorg, H., Manteghi, F. & Sheshmani, S. (2008). J. Iran. Chem. Soc.5, 184–227.
  • Aghabozorg, H., Ramezanipour, F., Soleimannejad, J., Sharif, M. A., Shokrollahi, A., Shamsipur, M., Moghimi, A., Attar Gharamaleki, J., Lippolis, V. & Blake, A. J. (2008). Polish J Chem.82, 487–507.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Moghimi, A., Sharif, M. A. & Aghabozorg, H. (2004). Acta Cryst. E60, o1790–o1792.
  • Moghimi, A., Sharif, M. A., Shokrollahi, A., Shamsipur, M. & Aghabozorg, H. (2005). Z. Anorg. Allg. Chem.631, 902–908.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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