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Acta Cryst. (2008). E64, m564-m565    [ doi:10.1107/S1600536808006594 ]

4-(4-Pyridyl)pyridinium bis(pyridine-2,6-dicarboxylato)chromium(III) tetrahydrate

J. Soleimannejad, H. Aghabozorg and S. Hooshmand

Abstract top

The title compound, (C10H9N2)[Cr(C7H3NO4)2]·4H2O or (4,4'-bipyH)[Cr(pydc)2]·4H2O (where 4,4'-bipy is 4,4'-bipyridine and pydcH2 is pyridine-2,6-dicarboxylic acid), was synthesized by the reaction of chromium(III) chloride hexahydrate with pyridine-2,6-dicarboxylic acid and 4,4'-bipyridine in a 1:2:4 molar ratio in aqueous solution. This compound is composed of an anionic complex, [Cr(pydc)2]-, protonated 4,4'-bipyridine as a counter-ion, (4,4'-bipyH)+, and four uncoordinated water molecules. The anion is a six-coordinate complex with a distorted octahedral geometry around the CrIII atom, formed by two tridentate pyridine-2,6-dicarboxylate, pydc2-, groups. Intermolecular O-H...O, N-H...O and C-H...O hydrogen bonds, and C-O...[pi] stacking interactions (with distances of 3.3390 (13) and 3.4575 (13) Å) connect the various components into a supramolecular structure.

Comment top

The molecular structure of the title compound is shown in Fig. 1. Hydrogen bond lengths are given in Table 1. According to the crystal structure, the title compound is composed of an anionic complex, [Cr(pydc)2]-, protonated 4,4'-bipyridine as a counter ion, (4,4'-bipyH)+, and four uncoordinated water molecules.

The CrIII atom is six-coordinated by two pyridine-2,6-dicarboxylate, pydc2-, groups which act as a tridentate ligand through two O and one N atoms. The O8—Cr1—O1—C1 and O8—Cr1—O4—C7 torsion angles (-89.13 (9)° and 95.98 (9)°, repectively) show that these two pydc2- groups are perpendicular. So the anionic complex has distorted octahedral geometry around CrIII atom. For balancing the anionic complex, a protonated 4,4'-bipyridinium, (4,4'-bipyH)+, exists.

In the crystal structure of (4,4'-bipyH)[Cr(pydc)2].4H2O complex, the spaces between two layers of [Cr(pydc)2]- anions are filled with (4,4'-bipyH)+ cations and water molecules (Fig. 2). The angle between two planes passing through aromatic rings of (4,4'-bipyH)+ is 51.45 (6)°, indicating the flexibility of the C—C bond between two rings.

A considerable feature of title compound is the presence of C—O···π stacking interactions between C1—O2 and C7—O3 and Cg1 [Cg1 is centroid for N1/C2—C6 ring] with O···π distances of 3.3390 (13) Å (1 - x, 1 - y, -z) and 3.4575 (13) Å (-x, 1 - y, -z), respectively (Fig. 3).

Intermolecular O—H···O, N—H···O and C—H···O hydrogen bonds with D···A ranging from 2.6736 (14) Å to 3.4235 (18) Å (Table 1), ion pairing and C—O···π stacking interactions seem to be effective in the stabilization of the crystal structure, resulting in the formation of an interesting supramolecular structure.

Related literature top

For related literature, see: Aghabozorg, Attar Gharamaleki, Ghadermazi et al. (2007); Aghabozorg, Attar Gharamaleki, Ghasemikhah et al. (2007); Soleimannejad et al. (2007).

Experimental top

A solution of CrCl3.6H2O (133 mg, 0.5 mmol) in water (5 ml) was added to an aqueous solution of pyridine-2,6-dicarboxylic acid (167 mg, 1 mmol) and 4,4'-bipyridine (312 mg, 2 mmol) in water (10 ml) in a 1:2:4 molar ratio and refluxed for an hour. Purple crystals of the title compound were obtained after allowing the mixture to stand for two weeks at room temperature.

Refinement top

The H-atoms were included in calculated positions and treated as riding atoms, with the exception of H atoms on the water molecules. The latter were located in a low theta Fourier map and refined by a constrained rigid type geometry, where O—H = 0.85 Å and C—H = 0.95 Å with Uiso(H) = 1.2Ueq (parent O or C-atom).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Layered diagram of the title compound. The space between the two layers of [Cr(pydc)2]- fragments is filled with a layer of (4,4'-bipyH)+ cations and water molecules.
[Figure 3] Fig. 3. C—O···π Stacking interactions between C1—O2 and C7—O3 and Cg1 [Cg1 is centroid for N1/C2—C6 ring] with O···π distance of 3.3390 (13) Å (1 - x, 1 - y, -z) and 3.4575 (13) Å (-x, 1 - y, -z) (measured to the center of Cg1).
4-(4-Pyridyl)pyridinium bis(pyridine-2,6-dicarboxylato)chromium(III) tetrahydrate top
Crystal data top
(C10H9N2)[Cr(C7H3NO4)2]·4H2OZ = 2
Mr = 611.46F000 = 630
Triclinic, P1Dx = 1.591 Mg m−3
a = 9.3785 (19) ÅMo Kα radiation
λ = 0.71073 Å
b = 9.4106 (19) ÅCell parameters from 12230 reflections
c = 14.542 (3) Åθ = 2.2–35.8º
α = 84.71 (3)ºµ = 0.52 mm−1
β = 89.78 (3)ºT = 150 (2) K
γ = 87.25 (3)ºBlock, purple
V = 1276.5 (4) Å30.32 × 0.28 × 0.16 mm
Data collection top
Bruker SMART APEXII
diffractometer		10833 independent reflections
Radiation source: fine-focus sealed tube8883 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.026
Detector resolution: 100 pixels mm-1θmax = 36.1º
T = 150(2) Kθmin = 2.2º
ω scansh = −14→15
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		k = −15→14
Tmin = 0.851, Tmax = 0.921l = −23→24
31765 measured reflections
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)] = 0.038H-atom parameters constrained
wR(F2) = 0.103  w = 1/[σ2(Fo2) + (0.048P)2 + 0.4592P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
10833 reflectionsΔρmax = 0.60 e Å−3
370 parametersΔρmin = −0.57 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
(C10H9N2)[Cr(C7H3NO4)2]·4H2Oγ = 87.25 (3)º
Mr = 611.46V = 1276.5 (4) Å3
Triclinic, P1Z = 2
a = 9.3785 (19) ÅMo Kα
b = 9.4106 (19) ŵ = 0.52 mm−1
c = 14.542 (3) ÅT = 150 (2) K
α = 84.71 (3)º0.32 × 0.28 × 0.16 mm
β = 89.78 (3)º
Data collection top
Bruker SMART APEXII
diffractometer		10833 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		8883 reflections with I > 2σ(I)
Tmin = 0.851, Tmax = 0.921Rint = 0.026
31765 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.038370 parameters
wR(F2) = 0.103H-atom parameters constrained
S = 1.05Δρmax = 0.60 e Å−3
10833 reflectionsΔρmin = −0.57 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
xyzUiso*/Ueq
Cr10.266361 (19)0.491881 (19)0.195816 (11)0.01104 (4)
N10.26445 (10)0.49786 (10)0.05944 (6)0.01197 (16)
N20.24857 (10)0.48069 (10)0.33175 (6)0.01179 (15)
N30.72695 (12)0.97534 (12)0.45391 (7)0.0194 (2)
N40.77831 (12)0.99799 (11)0.93219 (7)0.01759 (19)
H4A0.77950.99550.99260.021*
O10.12674 (9)0.65329 (9)0.16270 (5)0.01546 (15)
O2−0.00659 (10)0.76524 (10)0.04713 (6)0.01965 (17)
O30.53501 (10)0.23112 (10)0.06204 (6)0.01963 (17)
O40.41631 (9)0.33790 (9)0.17374 (5)0.01495 (15)
O50.41777 (9)0.62055 (9)0.22808 (5)0.01508 (15)
O60.52644 (10)0.70866 (11)0.34625 (6)0.02158 (18)
O7−0.04989 (10)0.27542 (10)0.32192 (6)0.01938 (17)
O80.10916 (9)0.35918 (9)0.21729 (5)0.01460 (15)
O9−0.03988 (11)0.69399 (11)0.31867 (6)0.0244 (2)
H9B0.00510.68490.26850.029*
H9A−0.11010.75190.30360.029*
O100.72454 (10)0.88911 (10)0.27755 (6)0.01963 (17)
H10B0.65860.83350.29430.024*
H10A0.72800.93320.32590.024*
O110.75568 (11)0.04005 (11)0.11110 (6)0.0244 (2)
H11A0.7538−0.00990.16280.029*
H11B0.69180.10650.11460.029*
O120.62868 (11)0.32459 (12)0.32442 (7)0.0285 (2)
H12B0.58460.31880.27400.034*
H12A0.71440.29350.31820.034*
C10.08705 (12)0.67886 (12)0.07649 (8)0.01409 (18)
C20.17048 (12)0.58722 (12)0.01280 (7)0.01299 (18)
C30.15612 (13)0.58587 (13)−0.08223 (8)0.0166 (2)
H30.08980.6496−0.11630.020*
C40.24262 (14)0.48751 (14)−0.12579 (8)0.0186 (2)
H40.23480.4836−0.19060.022*
C50.34043 (13)0.39477 (13)−0.07555 (8)0.0168 (2)
H50.39980.3282−0.10520.020*
C60.34819 (12)0.40300 (12)0.01900 (7)0.01346 (18)
C70.44279 (12)0.31500 (12)0.08853 (8)0.01428 (19)
C80.43694 (12)0.63540 (12)0.31482 (8)0.01491 (19)
C90.33577 (12)0.55471 (12)0.37879 (7)0.01382 (18)
C100.32408 (13)0.55271 (13)0.47402 (7)0.0162 (2)
H100.38490.60630.50820.019*
C110.22016 (13)0.46959 (13)0.51800 (8)0.0173 (2)
H110.21150.46420.58330.021*
C120.12876 (13)0.39426 (12)0.46697 (7)0.01504 (19)
H120.05720.33830.49660.018*
C130.14545 (12)0.40345 (12)0.37187 (7)0.01239 (18)
C140.05814 (12)0.33886 (12)0.30060 (7)0.01412 (19)
C150.81914 (14)1.05946 (15)0.48966 (8)0.0212 (2)
H150.87851.11440.44860.025*
C160.83252 (14)1.07062 (14)0.58368 (8)0.0186 (2)
H160.90131.12950.60640.022*
C170.74259 (12)0.99342 (12)0.64399 (8)0.01442 (19)
C180.75518 (12)0.99884 (12)0.74499 (7)0.01396 (18)
C190.88777 (13)0.97587 (12)0.78816 (8)0.01581 (19)
H190.97160.96240.75250.019*
C200.89631 (13)0.97280 (13)0.88267 (8)0.0172 (2)
H200.98560.95290.91290.021*
C210.64985 (14)1.02645 (14)0.89264 (8)0.0185 (2)
H210.56941.04830.92950.022*
C220.63443 (13)1.02407 (13)0.79875 (8)0.0171 (2)
H220.54291.03940.77090.020*
C230.64325 (13)0.90875 (13)0.60749 (8)0.0167 (2)
H230.57830.85730.64660.020*
C240.64132 (14)0.90131 (13)0.51256 (8)0.0184 (2)
H240.57600.84070.48790.022*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cr10.01172 (8)0.01332 (8)0.00807 (7)−0.00023 (6)0.00025 (5)−0.00118 (5)
N10.0121 (4)0.0144 (4)0.0094 (3)−0.0014 (3)0.0007 (3)−0.0010 (3)
N20.0113 (4)0.0139 (4)0.0100 (3)0.0002 (3)−0.0004 (3)−0.0007 (3)
N30.0213 (5)0.0234 (5)0.0134 (4)0.0024 (4)−0.0006 (4)−0.0024 (4)
N40.0225 (5)0.0186 (4)0.0117 (4)−0.0026 (4)−0.0007 (3)−0.0005 (3)
O10.0172 (4)0.0169 (4)0.0119 (3)0.0024 (3)0.0004 (3)−0.0012 (3)
O20.0185 (4)0.0182 (4)0.0211 (4)0.0032 (3)−0.0019 (3)0.0021 (3)
O30.0178 (4)0.0206 (4)0.0205 (4)0.0040 (3)0.0026 (3)−0.0046 (3)
O40.0155 (4)0.0170 (4)0.0121 (3)0.0017 (3)−0.0003 (3)−0.0014 (3)
O50.0164 (4)0.0182 (4)0.0109 (3)−0.0033 (3)0.0015 (3)−0.0017 (3)
O60.0212 (4)0.0266 (5)0.0181 (4)−0.0094 (4)−0.0012 (3)−0.0044 (3)
O70.0160 (4)0.0223 (4)0.0201 (4)−0.0059 (3)0.0019 (3)−0.0010 (3)
O80.0150 (4)0.0178 (4)0.0111 (3)−0.0026 (3)−0.0003 (3)−0.0012 (3)
O90.0235 (5)0.0309 (5)0.0172 (4)0.0059 (4)0.0060 (3)0.0019 (4)
O100.0213 (4)0.0245 (4)0.0133 (3)−0.0037 (3)0.0023 (3)−0.0016 (3)
O110.0264 (5)0.0310 (5)0.0137 (4)0.0105 (4)0.0033 (3)0.0021 (3)
O120.0237 (5)0.0425 (6)0.0191 (4)−0.0003 (4)−0.0029 (4)−0.0023 (4)
C10.0135 (5)0.0144 (4)0.0142 (4)−0.0015 (4)0.0007 (4)0.0000 (4)
C20.0126 (4)0.0149 (4)0.0112 (4)−0.0021 (4)−0.0005 (3)0.0007 (3)
C30.0174 (5)0.0208 (5)0.0116 (4)−0.0040 (4)−0.0022 (4)0.0014 (4)
C40.0218 (6)0.0248 (6)0.0098 (4)−0.0059 (5)−0.0001 (4)−0.0024 (4)
C50.0181 (5)0.0212 (5)0.0120 (4)−0.0043 (4)0.0030 (4)−0.0047 (4)
C60.0134 (5)0.0160 (5)0.0114 (4)−0.0019 (4)0.0021 (3)−0.0026 (3)
C70.0137 (5)0.0149 (4)0.0145 (4)−0.0015 (4)0.0004 (4)−0.0025 (4)
C80.0150 (5)0.0171 (5)0.0129 (4)−0.0010 (4)0.0003 (4)−0.0026 (4)
C90.0136 (5)0.0169 (5)0.0110 (4)−0.0003 (4)−0.0001 (3)−0.0022 (3)
C100.0175 (5)0.0208 (5)0.0107 (4)0.0001 (4)−0.0012 (4)−0.0033 (4)
C110.0194 (5)0.0227 (5)0.0095 (4)0.0016 (4)0.0005 (4)−0.0014 (4)
C120.0154 (5)0.0177 (5)0.0115 (4)0.0009 (4)0.0019 (4)0.0012 (4)
C130.0110 (4)0.0148 (4)0.0112 (4)0.0010 (4)0.0000 (3)−0.0006 (3)
C140.0137 (5)0.0152 (4)0.0133 (4)0.0001 (4)0.0000 (3)−0.0007 (4)
C150.0224 (6)0.0262 (6)0.0146 (5)−0.0027 (5)0.0020 (4)0.0009 (4)
C160.0191 (5)0.0216 (5)0.0152 (4)−0.0043 (4)0.0003 (4)−0.0005 (4)
C170.0142 (5)0.0158 (5)0.0132 (4)0.0008 (4)−0.0003 (3)−0.0014 (4)
C180.0157 (5)0.0131 (4)0.0131 (4)−0.0009 (4)0.0000 (4)−0.0014 (3)
C190.0151 (5)0.0166 (5)0.0157 (4)0.0007 (4)−0.0006 (4)−0.0026 (4)
C200.0189 (5)0.0170 (5)0.0155 (4)0.0005 (4)−0.0029 (4)−0.0007 (4)
C210.0189 (5)0.0216 (5)0.0153 (4)−0.0027 (4)0.0035 (4)−0.0020 (4)
C220.0149 (5)0.0207 (5)0.0155 (4)0.0002 (4)0.0005 (4)−0.0012 (4)
C230.0167 (5)0.0185 (5)0.0149 (4)−0.0016 (4)−0.0001 (4)−0.0014 (4)
C240.0194 (5)0.0199 (5)0.0162 (5)0.0002 (4)−0.0028 (4)−0.0037 (4)
Geometric parameters (Å, °) top
Cr1—N21.9767 (10)C3—C41.3958 (18)
Cr1—N11.9789 (10)C3—H30.9500
Cr1—O81.9829 (10)C4—C51.3956 (18)
Cr1—O11.9832 (11)C4—H40.9500
Cr1—O51.9944 (10)C5—C61.3865 (15)
Cr1—O42.0168 (10)C5—H50.9500
N1—C21.3312 (15)C6—C71.5091 (17)
N1—C61.3362 (15)C8—C91.5080 (17)
N2—C91.3300 (15)C9—C101.3872 (15)
N2—C131.3375 (15)C10—C111.3953 (18)
N3—C151.3378 (18)C10—H100.9500
N3—C241.3403 (17)C11—C121.3958 (18)
N4—C211.3416 (17)C11—H110.9500
N4—C201.3415 (17)C12—C131.3864 (15)
N4—H4A0.8760C12—H120.9500
O1—C11.3067 (14)C13—C141.5116 (16)
O2—C11.2185 (15)C15—C161.3874 (17)
O3—C71.2278 (14)C15—H150.9500
O4—C71.2982 (14)C16—C171.3942 (17)
O5—C81.2960 (13)C16—H160.9500
O6—C81.2270 (15)C17—C231.3920 (17)
O7—C141.2250 (15)C17—C181.4797 (16)
O8—C141.3018 (14)C18—C191.3937 (17)
O9—H9B0.8500C18—C221.3970 (17)
O9—H9A0.8500C19—C201.3745 (16)
O10—H10B0.8500C19—H190.9500
O10—H10A0.8499C20—H200.9500
O11—H11A0.8499C21—C221.3759 (17)
O11—H11B0.8500C21—H210.9500
O12—H12B0.8501C22—H220.9500
O12—H12A0.8500C23—C241.3889 (16)
C1—C21.5136 (16)C23—H230.9500
C2—C31.3902 (15)C24—H240.9500
N2—Cr1—N1174.39 (4)O4—C7—C6114.16 (10)
N2—Cr1—O878.67 (5)O6—C8—O5125.61 (11)
N1—Cr1—O896.21 (5)O6—C8—C9120.11 (10)
N2—Cr1—O199.21 (5)O5—C8—C9114.27 (10)
N1—Cr1—O178.40 (5)N2—C9—C10120.34 (11)
O8—Cr1—O190.66 (4)N2—C9—C8110.97 (9)
N2—Cr1—O578.69 (5)C10—C9—C8128.67 (11)
N1—Cr1—O5106.41 (5)C9—C10—C11117.90 (11)
O8—Cr1—O5157.36 (3)C9—C10—H10121.0
O1—Cr1—O593.07 (4)C11—C10—H10121.0
N2—Cr1—O4103.97 (5)C10—C11—C12120.65 (10)
N1—Cr1—O478.62 (5)C10—C11—H11119.7
O8—Cr1—O494.98 (4)C12—C11—H11119.7
O1—Cr1—O4156.79 (4)C13—C12—C11118.07 (11)
O5—Cr1—O490.33 (4)C13—C12—H12121.0
C2—N1—C6122.82 (9)C11—C12—H12121.0
C2—N1—Cr1118.44 (8)N2—C13—C12120.02 (10)
C6—N1—Cr1118.44 (8)N2—C13—C14111.00 (9)
C9—N2—C13122.97 (9)C12—C13—C14128.97 (10)
C9—N2—Cr1118.61 (8)O7—C14—O8125.24 (11)
C13—N2—Cr1118.36 (8)O7—C14—C13121.47 (10)
C15—N3—C24117.64 (11)O8—C14—C13113.29 (10)
C21—N4—C20122.19 (10)N3—C15—C16123.38 (12)
C21—N4—H4A115.4N3—C15—H15118.3
C20—N4—H4A122.4C16—C15—H15118.3
C1—O1—Cr1118.47 (8)C15—C16—C17118.44 (12)
C7—O4—Cr1117.10 (8)C15—C16—H16120.8
C8—O5—Cr1117.43 (8)C17—C16—H16120.8
C14—O8—Cr1118.01 (8)C23—C17—C16118.75 (11)
H9B—O9—H9A104.8C23—C17—C18120.75 (11)
H10B—O10—H10A98.4C16—C17—C18120.49 (11)
H11A—O11—H11B105.5C19—C18—C22118.99 (10)
H12B—O12—H12A108.4C19—C18—C17120.31 (11)
O2—C1—O1125.94 (11)C22—C18—C17120.69 (11)
O2—C1—C2121.35 (10)C20—C19—C18119.52 (11)
O1—C1—C2112.71 (10)C20—C19—H19120.2
N1—C2—C3120.49 (11)C18—C19—H19120.2
N1—C2—C1111.40 (9)N4—C20—C19119.90 (11)
C3—C2—C1128.08 (10)N4—C20—H20120.0
C2—C3—C4117.57 (11)C19—C20—H20120.0
C2—C3—H3121.2N4—C21—C22120.15 (11)
C4—C3—H3121.2N4—C21—H21119.9
C5—C4—C3121.00 (10)C22—C21—H21119.9
C5—C4—H4119.5C21—C22—C18119.12 (11)
C3—C4—H4119.5C21—C22—H22120.4
C6—C5—C4117.84 (11)C18—C22—H22120.4
C6—C5—H5121.1C24—C23—C17118.39 (11)
C4—C5—H5121.1C24—C23—H23120.8
N1—C6—C5120.28 (11)C17—C23—H23120.8
N1—C6—C7111.37 (9)N3—C24—C23123.35 (12)
C5—C6—C7128.35 (10)N3—C24—H24118.3
O3—C7—O4126.02 (11)C23—C24—H24118.3
O3—C7—C6119.82 (10)
N2—Cr1—N1—C259.1 (4)C2—N1—C6—C7−179.40 (10)
O8—Cr1—N1—C283.23 (9)Cr1—N1—C6—C7−5.76 (12)
O1—Cr1—N1—C2−6.16 (8)C4—C5—C6—N1−0.36 (17)
O5—Cr1—N1—C2−95.97 (9)C4—C5—C6—C7179.39 (11)
O4—Cr1—N1—C2177.08 (9)Cr1—O4—C7—O3176.09 (10)
N2—Cr1—N1—C6−114.8 (4)Cr1—O4—C7—C6−3.77 (12)
O8—Cr1—N1—C6−90.69 (9)N1—C6—C7—O3−173.79 (11)
O1—Cr1—N1—C6179.91 (9)C5—C6—C7—O36.45 (19)
O5—Cr1—N1—C690.11 (9)N1—C6—C7—O46.08 (14)
O4—Cr1—N1—C63.16 (8)C5—C6—C7—O4−173.68 (11)
N1—Cr1—N2—C9−156.0 (4)Cr1—O5—C8—O6178.97 (10)
O8—Cr1—N2—C9179.56 (9)Cr1—O5—C8—C9−1.96 (13)
O1—Cr1—N2—C9−91.62 (9)C13—N2—C9—C101.01 (17)
O5—Cr1—N2—C9−0.31 (8)Cr1—N2—C9—C10178.25 (8)
O4—Cr1—N2—C987.19 (9)C13—N2—C9—C8−177.80 (10)
N1—Cr1—N2—C1321.4 (4)Cr1—N2—C9—C8−0.56 (12)
O8—Cr1—N2—C13−3.07 (8)O6—C8—C9—N2−179.25 (11)
O1—Cr1—N2—C1385.75 (9)O5—C8—C9—N21.62 (14)
O5—Cr1—N2—C13177.06 (9)O6—C8—C9—C102.06 (19)
O4—Cr1—N2—C13−95.44 (9)O5—C8—C9—C10−177.07 (11)
N2—Cr1—O1—C1−167.76 (8)N2—C9—C10—C110.90 (17)
N1—Cr1—O1—C17.07 (8)C8—C9—C10—C11179.49 (11)
O8—Cr1—O1—C1−89.13 (9)C9—C10—C11—C12−1.70 (18)
O5—Cr1—O1—C1113.21 (9)C10—C11—C12—C130.66 (17)
O4—Cr1—O1—C115.18 (15)C9—N2—C13—C12−2.11 (17)
N2—Cr1—O4—C7175.52 (8)Cr1—N2—C13—C12−179.36 (8)
N1—Cr1—O4—C70.63 (8)C9—N2—C13—C14176.49 (10)
O8—Cr1—O4—C795.98 (9)Cr1—N2—C13—C14−0.76 (12)
O1—Cr1—O4—C7−7.47 (14)C11—C12—C13—N21.23 (16)
O5—Cr1—O4—C7−106.05 (9)C11—C12—C13—C14−177.09 (11)
N2—Cr1—O5—C81.31 (8)Cr1—O8—C14—O7170.02 (9)
N1—Cr1—O5—C8178.90 (8)Cr1—O8—C14—C13−9.45 (12)
O8—Cr1—O5—C80.96 (15)N2—C13—C14—O7−173.01 (11)
O1—Cr1—O5—C8100.09 (9)C12—C13—C14—O75.43 (19)
O4—Cr1—O5—C8−102.88 (9)N2—C13—C14—O86.48 (14)
N2—Cr1—O8—C147.16 (8)C12—C13—C14—O8−175.08 (11)
N1—Cr1—O8—C14−170.50 (8)C24—N3—C15—C161.7 (2)
O1—Cr1—O8—C14−92.10 (9)N3—C15—C16—C17−1.9 (2)
O5—Cr1—O8—C147.50 (15)C15—C16—C17—C23−0.10 (18)
O4—Cr1—O8—C14110.44 (9)C15—C16—C17—C18178.42 (11)
Cr1—O1—C1—O2173.01 (10)C23—C17—C18—C19128.56 (12)
Cr1—O1—C1—C2−6.65 (12)C16—C17—C18—C19−49.93 (16)
C6—N1—C2—C3−0.41 (17)C23—C17—C18—C22−50.12 (16)
Cr1—N1—C2—C3−174.05 (8)C16—C17—C18—C22131.39 (13)
C6—N1—C2—C1178.07 (10)C22—C18—C19—C202.58 (17)
Cr1—N1—C2—C14.43 (12)C17—C18—C19—C20−176.12 (11)
O2—C1—C2—N1−178.27 (11)C21—N4—C20—C190.06 (18)
O1—C1—C2—N11.41 (14)C18—C19—C20—N4−2.87 (18)
O2—C1—C2—C30.07 (18)C20—N4—C21—C223.03 (18)
O1—C1—C2—C3179.74 (11)N4—C21—C22—C18−3.20 (18)
N1—C2—C3—C40.40 (17)C19—C18—C22—C210.42 (17)
C1—C2—C3—C4−177.80 (11)C17—C18—C22—C21179.12 (11)
C2—C3—C4—C5−0.40 (18)C16—C17—C23—C242.07 (17)
C3—C4—C5—C60.38 (18)C18—C17—C23—C24−176.44 (11)
C2—N1—C6—C50.39 (17)C15—N3—C24—C230.49 (19)
Cr1—N1—C6—C5174.03 (9)C17—C23—C24—N3−2.37 (19)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O11i0.881.822.6736 (14)164
O9—H9B···O10.851.952.7944 (15)173
O9—H9A···O10ii0.851.982.8336 (16)176
O10—H10B···O60.851.862.7035 (16)172
O10—H10A···N30.851.942.7610 (15)162
O11—H11A···O10iii0.851.872.7132 (15)172
O11—H11B···O30.851.952.7282 (16)152
O12—H12B···O40.852.142.9569 (16)160
O12—H12A···O7iv0.852.213.0284 (16)162
C3—H3···O8v0.952.393.1688 (16)139
C5—H5···O5vi0.952.503.1737 (16)128
C10—H10···O12vii0.952.583.2867 (16)132
C11—H11···O9viii0.952.583.2271 (17)126
C15—H15···O7ix0.952.393.3002 (17)160
C16—H16···O9x0.952.493.4235 (18)169
C20—H20···O2xi0.952.513.0576 (16)117
C20—H20···O11xii0.952.453.2615 (17)143
C24—H24···O60.952.563.3634 (17)143
Symmetry codes: (i) x, y+1, z+1; (ii) x−1, y, z; (iii) x, y−1, z; (iv) x+1, y, z; (v) −x, −y+1, −z; (vi) −x+1, −y+1, −z; (vii) −x+1, −y+1, −z+1; (viii) −x, −y+1, −z+1; (ix) x+1, y+1, z; (x) −x+1, −y+2, −z+1; (xi) x+1, y, z+1; (xii) −x+2, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O11i0.881.822.6736 (14)164
O9—H9B···O10.851.952.7944 (15)173
O9—H9A···O10ii0.851.982.8336 (16)176
O10—H10B···O60.851.862.7035 (16)172
O10—H10A···N30.851.942.7610 (15)162
O11—H11A···O10iii0.851.872.7132 (15)172
O11—H11B···O30.851.952.7282 (16)152
O12—H12B···O40.852.142.9569 (16)160
O12—H12A···O7iv0.852.213.0284 (16)162
C3—H3···O8v0.952.393.1688 (16)139
C5—H5···O5vi0.952.503.1737 (16)128
C10—H10···O12vii0.952.583.2867 (16)132
C11—H11···O9viii0.952.583.2271 (17)126
C15—H15···O7ix0.952.393.3002 (17)160
C16—H16···O9x0.952.493.4235 (18)169
C20—H20···O2xi0.952.513.0576 (16)117
C20—H20···O11xii0.952.453.2615 (17)143
C24—H24···O60.952.563.3634 (17)143
Symmetry codes: (i) x, y+1, z+1; (ii) x−1, y, z; (iii) x, y−1, z; (iv) x+1, y, z; (v) −x, −y+1, −z; (vi) −x+1, −y+1, −z; (vii) −x+1, −y+1, −z+1; (viii) −x, −y+1, −z+1; (ix) x+1, y+1, z; (x) −x+1, −y+2, −z+1; (xi) x+1, y, z+1; (xii) −x+2, −y+1, −z+1.
Acknowledgements top

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references
References top

Aghabozorg, H., Attar Gharamaleki, J., Ghadermazi, M., Ghasemikhah, P. & Soleimannejad, J. (2007). Acta Cryst. E63, m1803–m1804.

Aghabozorg, H., Attar Gharamaleki, J., Ghasemikhah, P., Ghadermazi, M. & Soleimannejad, J. (2007). Acta Cryst. E63, m1710–m1711.

Bruker (2007). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Soleimannejad, J., Aghabozorg, H., Hooshmand, S. & Adams, H. (2007). Acta Cryst. E63, m3089–m3090.