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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 10| October 2011| Pages o2556-o2557
https://doi.org/10.1107/S1600536811035458

3,3′-Di­nitro­bis­­phenol A

Sainath Babu,a Chintan Pathak,a Satvika Uppu,b Conrad Jones,b Frank R. Fronczekc and Rao M. Uppua,b*

aDepartment of Environmental Toxicology, Southern University and A&M College, Baton Rouge, Louisiana 70813, USA, bDepartment of Chemistry, Southern University and A&M College, Baton Rouge, Louisiana 70813, USA, and cDepartment of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, USA
*Correspondence e-mail: rao_uppu@subr.edu

(Received 27 August 2011; accepted 31 August 2011; online 3 September 2011)

The title compound [systematic name: 2,2′-dinitro-4,4′-(propane-2,2-di­yl)diphenol], C15H14N2O6, crystallizes with two mol­ecules in the asymmetric unit. Both have a trans conformation for their OH groups, and in each, the two aromatic rings are nearly orthogonal, with dihedral angles of 88.30 (3) and 89.62 (2)°. The nitro groups are nearly in the planes of their attached benzene rings, with C—C—N—O torsion angles in the range 1.21 (17)–4.06 (17)°, and they each accept an intra­molecular O—H⋯O hydrogen bond from their adjacent OH groups. One of the OH groups also forms a weak inter­molecular O—H⋯O hydrogen bond.

Related literature

For background information on bis­phenol A and its uses and environmental effects, see: Hong-Mei & Nicell (2008[Hong-Mei, L. & Nicell, J. A. (2008). Bioresour. Technol. 99, 4428-4437.]); Lang et al. (2008[Lang, I. A., Galloway, T. S., Scarlett, A., Henley, W. E., Depledge, M., Wallace, R. B. & Melzer, D. (2008). JAMA, 300, 1303-1310.]); Masuda et al. (2005[Masuda, S., Terashima, Y., Sano, A., Kuruto, R., Sugiyama, Y., Shimoi, K., Tanji, K., Yoshioka, H., Terao, Y. & Kinae, N. (2005). Mutat. Res. 585, 137-146.]); Murrell (2006[Murrell, B. (2006). McNair Scholars J. 10, Article 10.]); Nakamura et al. (2011[Nakamura, S., Tezuka, Y., Ushiyama, A., Kawashima, C., Kitagawara, Y., Takahashi, K., Ohta, S. & Mashino, T. (2011). Toxicol. Lett. 203, 92-95.]); Richter et al. (2007[Richter, C. A., Birnbaum, L. S., Farabollini, F., Newbold, R. R., Rubin, B. S. & Talsness, C. E. (2007). Reprod. Toxicol. 24, 199-224.]); Sakuyama et al. (2003[Sakuyama, H., Endo, Y., Fujimoto, K. & Hatana, Y. (2003). J. Biosci. Bioeng. 96, 227-231.]); Toyoizumi et al. (2007[Toyoizumi, T., Deguchi, Y., Masuda, S. & Kinae, N. (2007). Biosci. Biotechnol. Biochem. 72, 2118-2123.]); Vandenberg et al. (2009[Vandenberg, L. N., Maffini, M. V., Sonnenschein, C., Rubin, B. S. & Soto, A. M. (2009). Endocr. Rev. 30, 75-95.]); Wang et al. (2007[Wang, X. J., Gao, N. Y., Sun, X. F. & Xu, B. (2007). Huan Jing Ke Xue, 28, 2544-2549.]). For related structures, see: Bel'skii et al. (1983[Bel'skii, V. K., Chernikova, N. Yu., Rotaru, V. K. & Kruchinin, M. M. (1983). Kristallografiya, 28, 685-689.]); Goldberg et al. (1991[Goldberg, I., Stein, Z., Tanaka, K. & Toda, F. (1991). J. Inclusion Phenom. Mol. Recognit. Chem. 10, 97-107.]); Lim & Tanski (2007[Lim, C. F. & Tanski, J. M. (2007). J. Chem. Crystallogr. 37, 587-595.]); Okada (1996[Okada, K. (1996). J. Mol. Struct. 380, 223-233.]); Wang et al. (1982[Wang, J. L., Tang, C. P. & Chen, Y. J. (1982). Acta Cryst. B38, 2286-2288.]). For graph-set analysis, see: Etter (1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]).

[Scheme 1]

Experimental

Crystal data

  • C15H14N2O6

  • Mr = 318.28

  • Triclinic, [P \overline 1]

  • a = 8.3989 (5) Å

  • b = 12.5738 (7) Å

  • c = 15.3757 (9) Å

  • α = 66.967 (2)°

  • β = 76.565 (2)°

  • γ = 77.833 (2)°

  • V = 1440.34 (14) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.98 mm−1

  • T = 90 K

  • 0.30 × 0.24 × 0.15 mm
Data collection

  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.758, Tmax = 0.867

  • 17716 measured reflections

  • 5276 independent reflections

  • 5010 reflections with I > 2σ(I)

  • Rint = 0.028
Refinement

  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.092

  • S = 1.04

  • 5276 reflections

  • 432 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯O3 0.88 (2) 1.80 (2) 2.5947 (14) 149.6 (18)
O2—H2⋯O5 0.844 (19) 1.856 (18) 2.5955 (13) 145.3 (16)
O2—H2⋯O5i 0.844 (19) 2.380 (18) 2.9832 (13) 128.8 (14)
O7—H7⋯O9 0.91 (2) 1.72 (2) 2.5667 (17) 154 (2)
O8—H8⋯O11 0.85 (2) 1.81 (2) 2.5747 (14) 148.8 (19)
Symmetry code: (i) -x+2, -y, -z+2.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811035458/hb6392sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811035458/hb6392Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811035458/hb6392Isup3.cml

checkCIF report


Comment top

Bisphenol A (BPA), a persistent organic pollutant in urban environments, ranks among the top 2% of high volume chemicals produced in the United States (Vandenberg et al., 2009). It is used in the making of printing materials, polycarbonate plastics and resins, all of which can become portals for human exposure. Studies using experimental animals have repeatedly shown that low level exposures to BPA can cause liver and brain damage, impaired insulin secretion, and a dysfunctional reproductive system (Richter et al., 2007). A recent report by Lang and colleagues (Lang et al., 2008), who analyzed the results of the first major epidemiologic study conducted by the National Health and Nutrition Examination Survey (NHANES) in 2003–2004, suggests wide-spread exposure to BPA in noninstitutionalized US populations where urinary levels of BPA are positively associated with higher incidence of cardiovascular diseases, diabetes, and abnormal concentrations of liver enzymes.

Bisphenol A can under go metabolic transformation by enzymes of cytochrome P450 system (Nakamura et al., 2011), peroxidases (Hong-Mei & Nicell, 2008; Sakuyama et al., 2003), and neutrophil and macrophage derived oxidants such as hypochlorous acid (Wang et al., 2007) and peroxynitrite (B.Martin, S. Babu, C. Pathak & R. Uppu, unpublished work). It is likely that the various putative metabolites of BPA formed in these reactions can act as secondary toxins and relay, at least, in part, the toxic effects of BPA. It has been shown, for instance, that nitrated and chlorinated products of BPA, which could be formed in vivo in hypochlorous acid and peroxynitrite mediated oxidations, exhibit higher toxicity than BPA itself and often elaborate mutagenic and/or genotoxic effects (Masuda et al., 2005; Toyoizumi et al., 2007). To better understand the molecular targets for nitrated products of BPA and the likely disruption of endocrine function, in the present report we have synthesized 3,3'-dinitrobisphenol A, (I), using acetone/nitric acid mixtures and characterized the product by IR, NMR, and GC-MS following necessary purification and recrystallization from ethanol. The structural co-ordinates obtained from the crystallographic studies are presented here with the anticipation that they could be used in computational studies aimed at understanding the molecular docking and energetics of binding to possible targets such as the androgen and estrogen receptors and serum proteins.

The two independent molecules in the asymmetric unit are illustrated in Fig. 1. In both, the conformation is trans, placing the OH groups on the opposite sides of the molecule. The phenyl groups are twisted with respect to the central C(CH3)2 group such that they are nearly perpendicular. The dihedral angle formed by the two phenyl planes is 89.62 (2)° in the molecule containing C1 through C15 and 88.30 (3)° in the second molecule. The nitro groups lie near the planes of the phenyl groups and form intramolecular hydrogen bonds with the adjacent OH groups. The C1—C2—N1—O3 torsion angle is 4.06 (17)°, and analogous torsion angles involving the other nitro groups are 2.11 (17)° for N2, 3.73 (18)° for N3, and 1.21 (17)° for N4. The intramolecular hydrogen bonds have O···O distances in the range 2.5667 (17) - 2.5955 (13) Å. One OH group, O2 also has an intermolecular acceptor at a longer distance, O2···O5 (at 2 - x, -y, 2 - z), 2.9832 (13) Å, forming centrosymmetric R22(4) rings (Etter, 1990), as shown in Fig. 2.

Similar intramolecular hydrogen bonds are found in the crystal structure of 2,2',6,6'-tetranitro-4,4-isopropylidenediphenol (Wang et al., 1982), which has two nitro groups adjacent to each OH. As in the title structure, the hydrogen- bonded nitro group lies near the plane of the phenyl group, while the other nitro group twists 46.5 (3)° out of plane.

Related literature top

For background information on bisphenol A and its uses and environmental effects, see: Hong-Mei & Nicell (2008); Lang et al. (2008); Masuda et al. (2005); Murrell (2006); Nakamura et al. (2011); Richter et al. (2007); Sakuyama et al. (2003); Toyoizumi et al. (2007); Vandenberg et al. (2009); Wang et al. (2007). For related structures, see: Bel'skii et al. (1983); Goldberg et al. (1991); Lim & Tanski (2007); Okada (1996); Wang et al. (1982). For graph-set analysis, see: Etter (1990).

Experimental top

Chemicals and solvents used in the synthesis and recrystallization of 3,3'-dinitrobisphenol A were obtained as follows: BPA and DMSO-d6 from Sigma-Aldrich (St. Louis, MO); HNO3 (70% w/v; density: 1.42 g/ml) from Fisher Scientific (Fairlawn, NJ); acetone from Mallinckrodt (Phillipsburg, NJ); and TRI-SIL/TBT reagent (a special formulation of silylation mixture consisting of TMS-imidazole with bis-TMS-acetamide and trimethylchlorosilane) from Pierce (Rockford, IL). Water used was ultrapure with resistance 18.2 MO/cm.

Nitration of BPA was performed according to the method of Murrell (2006) with minor modifications (Fig. 3). Briefly, BPA (5.1 g; 22.4 mmol) was dissolved in 50 ml of acetone in a round-bottom flask and HNO3 (4.2 ml; 66.3 mmol) was added drop-wise over a period of 30 min with continuous mixing. Throughout the course of nitration, the temperature of the flask was maintained at 0–5°C using an ice-water bath. At the end of HNO3 addition, the reaction mixture was brought to room temperature over a period of 1 h, while the contents were continuously stirred and then quenched in cold water. The yellow/orange precipitate was filtered and washed with an ice cold mixture of acetone and water (3:1). The precipitate was dried for 24 h at 37°C and purified further by recrystallization from ethanol.

The nitro product of BPA was dissolved in DMSO-d6 and analyzed for 1H– and 13C-NMR spectra using a Bruker Avance II 400 MHz spectrometer. The 1H-NMR showed peaks with chemical shifts (in p.p.m.) at δ: 10.86 (s, 2H), 7.71 (d, J = 2.54 Hz, 2H), 7.32 (dd, J = 2.50 and 2.50 Hz, 2H), 7.01(d, J = 8.55 Hz, 2H), and 1.60 (s, 6H) (Fig. 4). 13C-NMR spectrum showed chemical shifts (in p.p.m.) at δ: 30.28, (–CH3); 41.76 (C7), 119.62(C1), 122.51(C4), 134.55 (C6), 136.57(C3), and 141.01(C5), 150.83 (C2) (Fig. 5). The chemicals shifts and assignments of C and H shown are consistent with the structure shown in Fig. 1. Following silylation using the TRI-SIL/TBT reagent, the nitroproduct of BPA was analyzed by GC-MS using an Agilent Technologies 7890 A gas chromatograph equipped with an Agilent Technologies 5975 C V L triple-axis MSD and a HP-5MS capillary column (length: 30 m; internal diameter: 0.25 mm; and film thickness: 0.25 µm). Helium was used as the carrier gas (total flow: 3 ml/min; split ratio: 1:50) with temperature programming as follows: 40 °C for 2 min (isothermal); 20 °C/min up to 150 °C (ramp 1), 150 °C for 3 min (isothermal); 20 °C/min up to 300 °C (ramp 2), and 300 °C for 2 min (isothermal) (total run time: 20 min; temperature of the inlet port: 270°C). Under these conditions, the silylated product of nitro-BPA resolved as a single peak with a retention time of 19.61 min (Fig. 6). The ion chromatogram of the product eluting at 19.61 min showed a molecular ion (M+.) at m/z 462 (2.14%; relative to the base peak) and other fragments at m/z values of 447 (100%; base peak; [M-15]+ or [M—CH3]+), 252 (2.64%; [M-210]+ or [M—C9H12NO3Si]+), and 73 (42.54%; [M-389]+ or [M—C18H21N2O6Si]+ (Fig. 7). The proposed routes of fragmentation of the molecular ion of silylated 3,3'-dinitrobisphenol A, giving various daughter ions, are given in Fig. 8.

Yellow needles of 3,3'-dinitrobisphenol A were obtained from ethanol.

Refinement top

H atoms on C were placed in idealized positions, with C—H distances 0.95 - 0.98 Å. A torsional parameter was refined for each methyl group. Hydroxy H atom positions were refined. Uiso for H were assigned as 1.2 times Ueq of the attached atoms (1.5 for methyl and OH).

Structure description top

Bisphenol A (BPA), a persistent organic pollutant in urban environments, ranks among the top 2% of high volume chemicals produced in the United States (Vandenberg et al., 2009). It is used in the making of printing materials, polycarbonate plastics and resins, all of which can become portals for human exposure. Studies using experimental animals have repeatedly shown that low level exposures to BPA can cause liver and brain damage, impaired insulin secretion, and a dysfunctional reproductive system (Richter et al., 2007). A recent report by Lang and colleagues (Lang et al., 2008), who analyzed the results of the first major epidemiologic study conducted by the National Health and Nutrition Examination Survey (NHANES) in 2003–2004, suggests wide-spread exposure to BPA in noninstitutionalized US populations where urinary levels of BPA are positively associated with higher incidence of cardiovascular diseases, diabetes, and abnormal concentrations of liver enzymes.

Bisphenol A can under go metabolic transformation by enzymes of cytochrome P450 system (Nakamura et al., 2011), peroxidases (Hong-Mei & Nicell, 2008; Sakuyama et al., 2003), and neutrophil and macrophage derived oxidants such as hypochlorous acid (Wang et al., 2007) and peroxynitrite (B.Martin, S. Babu, C. Pathak & R. Uppu, unpublished work). It is likely that the various putative metabolites of BPA formed in these reactions can act as secondary toxins and relay, at least, in part, the toxic effects of BPA. It has been shown, for instance, that nitrated and chlorinated products of BPA, which could be formed in vivo in hypochlorous acid and peroxynitrite mediated oxidations, exhibit higher toxicity than BPA itself and often elaborate mutagenic and/or genotoxic effects (Masuda et al., 2005; Toyoizumi et al., 2007). To better understand the molecular targets for nitrated products of BPA and the likely disruption of endocrine function, in the present report we have synthesized 3,3'-dinitrobisphenol A, (I), using acetone/nitric acid mixtures and characterized the product by IR, NMR, and GC-MS following necessary purification and recrystallization from ethanol. The structural co-ordinates obtained from the crystallographic studies are presented here with the anticipation that they could be used in computational studies aimed at understanding the molecular docking and energetics of binding to possible targets such as the androgen and estrogen receptors and serum proteins.

The two independent molecules in the asymmetric unit are illustrated in Fig. 1. In both, the conformation is trans, placing the OH groups on the opposite sides of the molecule. The phenyl groups are twisted with respect to the central C(CH3)2 group such that they are nearly perpendicular. The dihedral angle formed by the two phenyl planes is 89.62 (2)° in the molecule containing C1 through C15 and 88.30 (3)° in the second molecule. The nitro groups lie near the planes of the phenyl groups and form intramolecular hydrogen bonds with the adjacent OH groups. The C1—C2—N1—O3 torsion angle is 4.06 (17)°, and analogous torsion angles involving the other nitro groups are 2.11 (17)° for N2, 3.73 (18)° for N3, and 1.21 (17)° for N4. The intramolecular hydrogen bonds have O···O distances in the range 2.5667 (17) - 2.5955 (13) Å. One OH group, O2 also has an intermolecular acceptor at a longer distance, O2···O5 (at 2 - x, -y, 2 - z), 2.9832 (13) Å, forming centrosymmetric R22(4) rings (Etter, 1990), as shown in Fig. 2.

Similar intramolecular hydrogen bonds are found in the crystal structure of 2,2',6,6'-tetranitro-4,4-isopropylidenediphenol (Wang et al., 1982), which has two nitro groups adjacent to each OH. As in the title structure, the hydrogen- bonded nitro group lies near the plane of the phenyl group, while the other nitro group twists 46.5 (3)° out of plane.

For background information on bisphenol A and its uses and environmental effects, see: Hong-Mei & Nicell (2008); Lang et al. (2008); Masuda et al. (2005); Murrell (2006); Nakamura et al. (2011); Richter et al. (2007); Sakuyama et al. (2003); Toyoizumi et al. (2007); Vandenberg et al. (2009); Wang et al. (2007). For related structures, see: Bel'skii et al. (1983); Goldberg et al. (1991); Lim & Tanski (2007); Okada (1996); Wang et al. (1982). For graph-set analysis, see: Etter (1990).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with ellipsoids at the 50% level, with H atoms having arbitrary radius.
[Figure 2] Fig. 2. The unit cell, showing hydrogen bonding.
[Figure 3] Fig. 3. Nitration of bisphenol A by nitric acid/acetone mixtures at 0–5°C.
[Figure 4] Fig. 4. 1H-NMR spectrum of 3,3'-dinitrobisphenol A.
[Figure 5] Fig. 5. 13C-NMR spectrum of 3,3'-dinitrobisphenol A.
[Figure 6] Fig. 6. Ion chromatogram of the silylated product of 3,3'- dinitrobisphenol A.
[Figure 7] Fig. 7. Electron ionization fragmentation of the silylated product of 3,3'-dintrobisphenol A.
[Figure 8] Fig. 8. Proposed routes of fragmentation of the molecular ion of silylated 3,3'-dinitrobisphenol A.
2,2'-dinitro-4,4'-(propane-2,2-diyl)diphenol top
Crystal data top
C15H14N2O6Z = 4
Mr = 318.28F(000) = 664
Triclinic, P1Dx = 1.468 Mg m−3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54178 Å
a = 8.3989 (5) ÅCell parameters from 9978 reflections
b = 12.5738 (7) Åθ = 3.8–69.4°
c = 15.3757 (9) ŵ = 0.98 mm−1
α = 66.967 (2)°T = 90 K
β = 76.565 (2)°Needle fragment, yellow
γ = 77.833 (2)°0.30 × 0.24 × 0.15 mm
V = 1440.34 (14) Å3
Data collection top
Bruker Kappa APEXII CCD
diffractometer		5276 independent reflections
Radiation source: fine-focus sealed tube5010 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
φ and ω scansθmax = 69.8°, θmin = 3.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		h = −8→10
Tmin = 0.758, Tmax = 0.867k = −15→15
17716 measured reflectionsl = −16→18
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)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092 w = 1/[σ2(Fo2) + (0.0456P)2 + 0.5723P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
5276 reflectionsΔρmax = 0.32 e Å−3
432 parametersΔρmin = −0.19 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0019 (2)
Crystal data top
C15H14N2O6γ = 77.833 (2)°
Mr = 318.28V = 1440.34 (14) Å3
Triclinic, P1Z = 4
a = 8.3989 (5) ÅCu Kα radiation
b = 12.5738 (7) ŵ = 0.98 mm−1
c = 15.3757 (9) ÅT = 90 K
α = 66.967 (2)°0.30 × 0.24 × 0.15 mm
β = 76.565 (2)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer		5276 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		5010 reflections with I > 2σ(I)
Tmin = 0.758, Tmax = 0.867Rint = 0.028
17716 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.092H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.32 e Å−3
5276 reflectionsΔρmin = −0.19 e Å−3
432 parameters
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
O10.22904 (13)0.58866 (9)0.48806 (7)0.0294 (2)
H10.123 (3)0.5893 (17)0.4943 (14)0.044*
O20.73621 (11)0.03318 (7)0.95361 (6)0.02063 (19)
H20.829 (2)0.0338 (15)0.9658 (12)0.031*
O3−0.07766 (12)0.57717 (8)0.56906 (7)0.0292 (2)
O4−0.15232 (11)0.55090 (9)0.71963 (7)0.0287 (2)
O50.97246 (11)0.12665 (8)0.96739 (7)0.0272 (2)
O60.93932 (12)0.30789 (8)0.95141 (9)0.0350 (3)
N1−0.04492 (13)0.55927 (9)0.64899 (8)0.0224 (2)
N20.88736 (13)0.22431 (9)0.95078 (8)0.0212 (2)
C10.25048 (16)0.56709 (11)0.57760 (9)0.0216 (3)
C20.12602 (15)0.54936 (10)0.65832 (9)0.0194 (3)
C30.16117 (15)0.52384 (10)0.74984 (9)0.0176 (2)
H30.07430.51100.80340.021*
C40.32013 (14)0.51728 (10)0.76286 (8)0.0163 (2)
C50.44549 (15)0.53631 (10)0.68122 (9)0.0197 (3)
H50.55620.53180.68860.024*
C60.41164 (16)0.56111 (11)0.59161 (9)0.0225 (3)
H60.49880.57440.53830.027*
C70.36794 (14)0.48809 (10)0.86086 (8)0.0162 (2)
C80.47801 (14)0.36988 (10)0.88453 (8)0.0153 (2)
C90.63366 (14)0.35074 (10)0.90618 (8)0.0166 (2)
H90.68050.41370.90540.020*
C100.72413 (14)0.23857 (10)0.92944 (8)0.0169 (2)
C110.66033 (15)0.14318 (10)0.93106 (8)0.0167 (2)
C120.50322 (15)0.16441 (10)0.90675 (8)0.0177 (2)
H120.45690.10230.90560.021*
C130.41528 (14)0.27400 (10)0.88453 (8)0.0172 (2)
H130.30860.28590.86860.021*
C140.45545 (14)0.58693 (10)0.85565 (9)0.0178 (2)
H14A0.55570.59330.80720.027*
H14B0.48510.56970.91820.027*
H14C0.38120.66070.83820.027*
C150.21674 (14)0.47754 (11)0.94100 (9)0.0187 (2)
H15A0.14250.55150.92600.028*
H15B0.25310.45931.00200.028*
H15C0.15820.41510.94610.028*
O70.02131 (15)−0.30550 (9)0.30590 (8)0.0365 (3)
H7−0.080 (3)−0.2877 (18)0.2880 (15)0.055*
O80.33303 (13)0.14153 (10)0.57674 (7)0.0320 (2)
H80.435 (3)0.1460 (17)0.5692 (14)0.048*
O9−0.24524 (14)−0.19241 (10)0.24194 (8)0.0392 (3)
O10−0.28330 (13)−0.00440 (11)0.18519 (9)0.0416 (3)
O110.63606 (12)0.15267 (9)0.49364 (7)0.0294 (2)
O120.71117 (11)0.15854 (9)0.34782 (7)0.0308 (2)
N3−0.20026 (14)−0.09626 (11)0.22333 (9)0.0295 (3)
N40.60419 (13)0.15289 (9)0.41816 (8)0.0229 (2)
C160.05818 (17)−0.19784 (11)0.28560 (9)0.0243 (3)
C17−0.04478 (15)−0.09397 (12)0.24732 (9)0.0221 (3)
C18−0.00188 (15)0.01496 (11)0.23027 (8)0.0194 (3)
H18−0.07540.08380.20530.023*
C190.14606 (14)0.02296 (10)0.24948 (8)0.0169 (2)
C200.25088 (15)−0.08150 (11)0.28611 (8)0.0200 (3)
H200.3541−0.07780.29940.024*
C210.20879 (17)−0.18877 (11)0.30335 (9)0.0238 (3)
H210.2833−0.25730.32760.029*
C220.20487 (14)0.13939 (10)0.22818 (8)0.0179 (2)
C230.24781 (15)0.13806 (10)0.32030 (8)0.0171 (2)
C240.40497 (15)0.14409 (10)0.32903 (9)0.0180 (2)
H240.49280.14740.27680.022*
C250.43654 (15)0.14534 (10)0.41427 (9)0.0194 (3)
C260.31108 (16)0.14011 (11)0.49325 (9)0.0225 (3)
C270.15235 (16)0.13151 (11)0.48457 (9)0.0234 (3)
H270.06460.12640.53710.028*
C280.12238 (15)0.13041 (11)0.40085 (9)0.0203 (3)
H280.01360.12430.39700.024*
C290.07223 (16)0.24398 (11)0.19345 (9)0.0223 (3)
H29A−0.02810.23480.24190.033*
H29B0.04690.24770.13320.033*
H29C0.11330.31610.18320.033*
C300.35372 (16)0.15349 (11)0.14636 (9)0.0216 (3)
H30A0.39340.22790.13050.032*
H30B0.32030.15230.08980.032*
H30C0.44230.08930.16660.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0321 (5)0.0389 (6)0.0185 (5)−0.0099 (4)−0.0084 (4)−0.0066 (4)
O20.0209 (4)0.0159 (4)0.0250 (5)−0.0003 (3)−0.0054 (4)−0.0075 (3)
O30.0303 (5)0.0322 (5)0.0299 (5)−0.0016 (4)−0.0171 (4)−0.0107 (4)
O40.0172 (4)0.0393 (6)0.0358 (5)−0.0012 (4)−0.0053 (4)−0.0207 (4)
O50.0218 (5)0.0205 (4)0.0398 (5)0.0046 (4)−0.0127 (4)−0.0110 (4)
O60.0249 (5)0.0259 (5)0.0648 (7)0.0000 (4)−0.0213 (5)−0.0216 (5)
N10.0219 (5)0.0199 (5)0.0285 (6)−0.0001 (4)−0.0103 (5)−0.0100 (4)
N20.0191 (5)0.0199 (5)0.0266 (5)0.0000 (4)−0.0077 (4)−0.0097 (4)
C10.0280 (6)0.0189 (6)0.0184 (6)−0.0035 (5)−0.0071 (5)−0.0053 (5)
C20.0185 (6)0.0163 (6)0.0248 (6)−0.0004 (4)−0.0078 (5)−0.0073 (5)
C30.0175 (6)0.0153 (5)0.0204 (6)−0.0010 (4)−0.0031 (5)−0.0075 (5)
C40.0172 (5)0.0138 (5)0.0182 (6)−0.0009 (4)−0.0042 (4)−0.0058 (4)
C50.0171 (6)0.0206 (6)0.0215 (6)−0.0026 (5)−0.0034 (5)−0.0077 (5)
C60.0226 (6)0.0253 (6)0.0188 (6)−0.0063 (5)0.0001 (5)−0.0077 (5)
C70.0148 (5)0.0164 (6)0.0179 (6)−0.0019 (4)−0.0036 (4)−0.0064 (4)
C80.0167 (5)0.0168 (6)0.0120 (5)−0.0026 (4)−0.0011 (4)−0.0053 (4)
C90.0179 (6)0.0167 (6)0.0168 (5)−0.0038 (4)−0.0027 (4)−0.0072 (4)
C100.0150 (5)0.0201 (6)0.0163 (5)−0.0024 (4)−0.0030 (4)−0.0071 (5)
C110.0203 (6)0.0159 (6)0.0123 (5)−0.0023 (4)0.0000 (4)−0.0049 (4)
C120.0203 (6)0.0179 (6)0.0169 (6)−0.0070 (4)−0.0006 (4)−0.0075 (5)
C130.0157 (5)0.0207 (6)0.0163 (5)−0.0041 (4)−0.0025 (4)−0.0070 (5)
C140.0183 (6)0.0162 (6)0.0204 (6)−0.0021 (4)−0.0050 (5)−0.0071 (5)
C150.0161 (5)0.0220 (6)0.0189 (6)−0.0020 (4)−0.0021 (5)−0.0092 (5)
O70.0443 (6)0.0244 (5)0.0442 (6)−0.0143 (5)0.0001 (5)−0.0154 (5)
O80.0334 (5)0.0488 (6)0.0207 (5)−0.0137 (5)−0.0033 (4)−0.0161 (4)
O90.0400 (6)0.0526 (7)0.0410 (6)−0.0249 (5)0.0004 (5)−0.0283 (5)
O100.0264 (5)0.0546 (7)0.0569 (7)0.0005 (5)−0.0169 (5)−0.0316 (6)
O110.0324 (5)0.0335 (5)0.0261 (5)−0.0102 (4)−0.0129 (4)−0.0075 (4)
O120.0200 (5)0.0425 (6)0.0307 (5)−0.0095 (4)−0.0009 (4)−0.0132 (4)
N30.0243 (6)0.0443 (7)0.0306 (6)−0.0096 (5)−0.0001 (5)−0.0246 (6)
N40.0236 (5)0.0203 (5)0.0247 (6)−0.0057 (4)−0.0068 (5)−0.0051 (4)
C160.0325 (7)0.0219 (6)0.0199 (6)−0.0096 (5)0.0034 (5)−0.0105 (5)
C170.0209 (6)0.0308 (7)0.0197 (6)−0.0074 (5)0.0009 (5)−0.0149 (5)
C180.0201 (6)0.0225 (6)0.0164 (6)−0.0006 (5)−0.0021 (4)−0.0096 (5)
C190.0193 (6)0.0188 (6)0.0128 (5)−0.0027 (5)−0.0006 (4)−0.0070 (4)
C200.0206 (6)0.0216 (6)0.0173 (6)−0.0019 (5)−0.0039 (5)−0.0066 (5)
C210.0293 (7)0.0186 (6)0.0193 (6)−0.0001 (5)−0.0023 (5)−0.0050 (5)
C220.0190 (6)0.0173 (6)0.0172 (6)−0.0027 (5)−0.0027 (5)−0.0060 (5)
C230.0197 (6)0.0137 (5)0.0175 (6)−0.0027 (4)−0.0028 (5)−0.0053 (4)
C240.0188 (6)0.0156 (5)0.0174 (6)−0.0035 (4)−0.0007 (4)−0.0044 (4)
C250.0196 (6)0.0172 (6)0.0212 (6)−0.0051 (4)−0.0046 (5)−0.0047 (5)
C260.0288 (7)0.0224 (6)0.0178 (6)−0.0060 (5)−0.0037 (5)−0.0078 (5)
C270.0229 (6)0.0276 (7)0.0200 (6)−0.0071 (5)0.0027 (5)−0.0104 (5)
C280.0181 (6)0.0221 (6)0.0216 (6)−0.0045 (5)−0.0016 (5)−0.0088 (5)
C290.0257 (6)0.0176 (6)0.0230 (6)−0.0006 (5)−0.0070 (5)−0.0060 (5)
C300.0240 (6)0.0235 (6)0.0171 (6)−0.0072 (5)−0.0002 (5)−0.0068 (5)
Geometric parameters (Å, º) top
O1—C11.3431 (15)O7—C161.3516 (16)
O1—H10.88 (2)O7—H70.91 (2)
O2—C111.3398 (14)O8—C261.3460 (15)
O2—H20.844 (19)O8—H80.85 (2)
O3—N11.2456 (14)O9—N31.2481 (16)
O4—N11.2246 (15)O10—N31.2185 (17)
O5—N21.2464 (14)O11—N41.2490 (14)
O6—N21.2240 (14)O12—N41.2237 (15)
N1—C21.4504 (16)N3—C171.4457 (17)
N2—C101.4418 (15)N4—C251.4475 (16)
C1—C21.4005 (18)C16—C211.3903 (19)
C1—C61.4014 (18)C16—C171.3997 (19)
C2—C31.4037 (17)C17—C181.3991 (18)
C3—C41.3763 (17)C18—C191.3739 (17)
C3—H30.9500C18—H180.9500
C4—C51.4138 (17)C19—C201.4077 (17)
C4—C71.5339 (16)C19—C221.5326 (16)
C5—C61.3729 (18)C20—C211.3755 (18)
C5—H50.9500C20—H200.9500
C6—H60.9500C21—H210.9500
C7—C81.5331 (16)C22—C231.5340 (16)
C7—C151.5377 (16)C22—C291.5378 (16)
C7—C141.5398 (15)C22—C301.5379 (16)
C8—C91.3729 (17)C23—C241.3779 (17)
C8—C131.4137 (16)C23—C281.4128 (17)
C9—C101.4051 (17)C24—C251.4028 (17)
C9—H90.9500C24—H240.9500
C10—C111.4028 (17)C25—C261.4006 (18)
C11—C121.3981 (17)C26—C271.4004 (18)
C12—C131.3715 (17)C27—C281.3736 (18)
C12—H120.9500C27—H270.9500
C13—H130.9500C28—H280.9500
C14—H14A0.9800C29—H29A0.9800
C14—H14B0.9800C29—H29B0.9800
C14—H14C0.9800C29—H29C0.9800
C15—H15A0.9800C30—H30A0.9800
C15—H15B0.9800C30—H30B0.9800
C15—H15C0.9800C30—H30C0.9800
C1—O1—H1103.2 (13)C16—O7—H7100.9 (14)
C11—O2—H2106.1 (12)C26—O8—H8104.9 (14)
O4—N1—O3122.20 (10)O10—N3—O9121.88 (12)
O4—N1—C2119.00 (10)O10—N3—C17119.13 (12)
O3—N1—C2118.80 (11)O9—N3—C17118.99 (12)
O6—N2—O5121.75 (10)O12—N4—O11121.70 (11)
O6—N2—C10119.57 (10)O12—N4—C25119.28 (10)
O5—N2—C10118.68 (10)O11—N4—C25119.02 (10)
O1—C1—C2125.71 (12)O7—C16—C21118.19 (12)
O1—C1—C6117.15 (11)O7—C16—C17124.50 (13)
C2—C1—C6117.14 (11)C21—C16—C17117.31 (11)
C1—C2—C3121.63 (11)C18—C17—C16121.91 (12)
C1—C2—N1120.44 (11)C18—C17—N3117.65 (12)
C3—C2—N1117.92 (11)C16—C17—N3120.45 (12)
C4—C3—C2120.71 (11)C19—C18—C17120.35 (11)
C4—C3—H3119.6C19—C18—H18119.8
C2—C3—H3119.6C17—C18—H18119.8
C3—C4—C5117.64 (11)C18—C19—C20117.60 (11)
C3—C4—C7123.54 (10)C18—C19—C22123.22 (11)
C5—C4—C7118.81 (10)C20—C19—C22119.09 (10)
C6—C5—C4121.82 (11)C21—C20—C19122.20 (12)
C6—C5—H5119.1C21—C20—H20118.9
C4—C5—H5119.1C19—C20—H20118.9
C5—C6—C1121.04 (11)C20—C21—C16120.59 (12)
C5—C6—H6119.5C20—C21—H21119.7
C1—C6—H6119.5C16—C21—H21119.7
C8—C7—C4107.24 (9)C19—C22—C23108.55 (9)
C8—C7—C15108.16 (9)C19—C22—C29112.24 (10)
C4—C7—C15112.37 (9)C23—C22—C29108.67 (9)
C8—C7—C14112.85 (9)C19—C22—C30107.55 (9)
C4—C7—C14108.79 (9)C23—C22—C30112.75 (10)
C15—C7—C14107.52 (9)C29—C22—C30107.13 (10)
C9—C8—C13117.69 (10)C24—C23—C28117.43 (11)
C9—C8—C7124.27 (10)C24—C23—C22123.05 (10)
C13—C8—C7118.04 (10)C28—C23—C22119.52 (10)
C8—C9—C10120.35 (11)C23—C24—C25120.66 (11)
C8—C9—H9119.8C23—C24—H24119.7
C10—C9—H9119.8C25—C24—H24119.7
C11—C10—C9121.81 (11)C26—C25—C24121.68 (11)
C11—C10—N2120.50 (10)C26—C25—N4120.59 (11)
C9—C10—N2117.69 (10)C24—C25—N4117.73 (11)
O2—C11—C12116.73 (10)O8—C26—C27118.06 (11)
O2—C11—C10126.02 (11)O8—C26—C25124.59 (12)
C12—C11—C10117.25 (11)C27—C26—C25117.35 (11)
C13—C12—C11120.63 (11)C28—C27—C26120.63 (11)
C13—C12—H12119.7C28—C27—H27119.7
C11—C12—H12119.7C26—C27—H27119.7
C12—C13—C8122.25 (11)C27—C28—C23122.24 (11)
C12—C13—H13118.9C27—C28—H28118.9
C8—C13—H13118.9C23—C28—H28118.9
C7—C14—H14A109.5C22—C29—H29A109.5
C7—C14—H14B109.5C22—C29—H29B109.5
H14A—C14—H14B109.5H29A—C29—H29B109.5
C7—C14—H14C109.5C22—C29—H29C109.5
H14A—C14—H14C109.5H29A—C29—H29C109.5
H14B—C14—H14C109.5H29B—C29—H29C109.5
C7—C15—H15A109.5C22—C30—H30A109.5
C7—C15—H15B109.5C22—C30—H30B109.5
H15A—C15—H15B109.5H30A—C30—H30B109.5
C7—C15—H15C109.5C22—C30—H30C109.5
H15A—C15—H15C109.5H30A—C30—H30C109.5
H15B—C15—H15C109.5H30B—C30—H30C109.5
O1—C1—C2—C3178.07 (11)O7—C16—C17—C18178.18 (11)
C6—C1—C2—C3−1.52 (18)C21—C16—C17—C18−2.11 (18)
O1—C1—C2—N1−3.15 (19)O7—C16—C17—N3−2.24 (19)
C6—C1—C2—N1177.26 (11)C21—C16—C17—N3177.47 (11)
O4—N1—C2—C1−175.24 (11)O10—N3—C17—C183.63 (17)
O3—N1—C2—C14.06 (17)O9—N3—C17—C18−176.67 (11)
O4—N1—C2—C33.58 (16)O10—N3—C17—C16−175.96 (12)
O3—N1—C2—C3−177.12 (10)O9—N3—C17—C163.73 (18)
C1—C2—C3—C41.06 (18)C16—C17—C18—C191.12 (18)
N1—C2—C3—C4−177.74 (10)N3—C17—C18—C19−178.47 (10)
C2—C3—C4—C5−0.42 (17)C17—C18—C19—C200.22 (17)
C2—C3—C4—C7−179.08 (10)C17—C18—C19—C22177.00 (10)
C3—C4—C5—C60.32 (17)C18—C19—C20—C21−0.52 (18)
C7—C4—C5—C6179.05 (11)C22—C19—C20—C21−177.43 (11)
C4—C5—C6—C1−0.85 (19)C19—C20—C21—C16−0.53 (19)
O1—C1—C6—C5−178.22 (11)O7—C16—C21—C20−178.48 (11)
C2—C1—C6—C51.41 (18)C17—C16—C21—C201.79 (18)
C3—C4—C7—C8113.79 (12)C18—C19—C22—C23126.24 (11)
C5—C4—C7—C8−64.86 (13)C20—C19—C22—C23−57.03 (13)
C3—C4—C7—C15−4.93 (15)C18—C19—C22—C296.11 (16)
C5—C4—C7—C15176.43 (10)C20—C19—C22—C29−177.16 (10)
C3—C4—C7—C14−123.86 (12)C18—C19—C22—C30−111.48 (12)
C5—C4—C7—C1457.49 (13)C20—C19—C22—C3065.25 (13)
C4—C7—C8—C9124.49 (11)C19—C22—C23—C24116.54 (12)
C15—C7—C8—C9−114.11 (12)C29—C22—C23—C24−121.12 (12)
C14—C7—C8—C94.71 (16)C30—C22—C23—C24−2.51 (16)
C4—C7—C8—C13−55.80 (13)C19—C22—C23—C28−63.49 (13)
C15—C7—C8—C1365.61 (13)C29—C22—C23—C2858.84 (14)
C14—C7—C8—C13−175.57 (10)C30—C22—C23—C28177.46 (10)
C13—C8—C9—C10−1.38 (16)C28—C23—C24—C25−1.49 (17)
C7—C8—C9—C10178.33 (10)C22—C23—C24—C25178.47 (10)
C8—C9—C10—C110.28 (17)C23—C24—C25—C260.25 (18)
C8—C9—C10—N2179.55 (10)C23—C24—C25—N4−179.43 (10)
O6—N2—C10—C11−178.15 (11)O12—N4—C25—C26−179.27 (11)
O5—N2—C10—C112.44 (17)O11—N4—C25—C261.21 (17)
O6—N2—C10—C92.57 (17)O12—N4—C25—C240.42 (17)
O5—N2—C10—C9−176.84 (11)O11—N4—C25—C24−179.11 (10)
C9—C10—C11—O2−179.00 (11)C24—C25—C26—O8−179.66 (12)
N2—C10—C11—O21.75 (18)N4—C25—C26—O80.01 (19)
C9—C10—C11—C121.15 (17)C24—C25—C26—C271.07 (18)
N2—C10—C11—C12−178.10 (10)N4—C25—C26—C27−179.26 (11)
O2—C11—C12—C13178.70 (10)O8—C26—C27—C28179.59 (12)
C10—C11—C12—C13−1.43 (17)C25—C26—C27—C28−1.10 (19)
C11—C12—C13—C80.33 (18)C26—C27—C28—C23−0.17 (19)
C9—C8—C13—C121.11 (17)C24—C23—C28—C271.48 (18)
C7—C8—C13—C12−178.63 (10)C22—C23—C28—C27−178.49 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O30.88 (2)1.80 (2)2.5947 (14)149.6 (18)
O2—H2···O50.844 (19)1.856 (18)2.5955 (13)145.3 (16)
O2—H2···O5i0.844 (19)2.380 (18)2.9832 (13)128.8 (14)
O7—H7···O90.91 (2)1.72 (2)2.5667 (17)154 (2)
O8—H8···O110.85 (2)1.81 (2)2.5747 (14)148.8 (19)
Symmetry code: (i) −x+2, −y, −z+2.

Experimental details

Crystal data
Chemical formulaC15H14N2O6
Mr318.28
Crystal system, space groupTriclinic, P1
Temperature (K)90
a, b, c (Å)8.3989 (5), 12.5738 (7), 15.3757 (9)
α, β, γ (°)66.967 (2), 76.565 (2), 77.833 (2)
V (Å3)1440.34 (14)
Z4
Radiation typeCu Kα
µ (mm−1)0.98
Crystal size (mm)0.30 × 0.24 × 0.15
Data collection
DiffractometerBruker Kappa APEXII CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.758, 0.867
No. of measured, independent and
observed [I > 2σ(I)] reflections		17716, 5276, 5010
Rint0.028
(sin θ/λ)max (Å−1)0.609
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.092, 1.04
No. of reflections5276
No. of parameters432
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.32, −0.19

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O30.88 (2)1.80 (2)2.5947 (14)149.6 (18)
O2—H2···O50.844 (19)1.856 (18)2.5955 (13)145.3 (16)
O2—H2···O5i0.844 (19)2.380 (18)2.9832 (13)128.8 (14)
O7—H7···O90.91 (2)1.72 (2)2.5667 (17)154 (2)
O8—H8···O110.85 (2)1.81 (2)2.5747 (14)148.8 (19)
Symmetry code: (i) −x+2, −y, −z+2.
 

Acknowledgements

This publication was made possible by National Institutes of Health Grant No. P20RR16456 (the BRIN Program of the National Center for Research Resources), National Science Foundation Grant No. HRD-1043316 (the HBCU-UP ACE implementation program), and the US Department of Education Grant No. PO31B040030 (Title III, Part B - Strengthening Historically Black Graduate Institutions). The contents of this publication are solely the responsibility of authors and do not necessarily represent the official views of the NSF, NIH or the US Department of Education.

References

First citationBel'skii, V. K., Chernikova, N. Yu., Rotaru, V. K. & Kruchinin, M. M. (1983). Kristallografiya, 28, 685–689.  CAS Google Scholar
 First citationBruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationEtter, M. C. (1990). Acc. Chem. Res. 23, 120–126.  CrossRef CAS Web of Science Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationGoldberg, I., Stein, Z., Tanaka, K. & Toda, F. (1991). J. Inclusion Phenom. Mol. Recognit. Chem. 10, 97–107.  CSD CrossRef CAS Web of Science Google Scholar
 First citationHong-Mei, L. & Nicell, J. A. (2008). Bioresour. Technol. 99, 4428–4437.  PubMed Google Scholar
 First citationLang, I. A., Galloway, T. S., Scarlett, A., Henley, W. E., Depledge, M., Wallace, R. B. & Melzer, D. (2008). JAMA, 300, 1303–1310.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationLim, C. F. & Tanski, J. M. (2007). J. Chem. Crystallogr. 37, 587–595.  Web of Science CSD CrossRef CAS Google Scholar
 First citationMasuda, S., Terashima, Y., Sano, A., Kuruto, R., Sugiyama, Y., Shimoi, K., Tanji, K., Yoshioka, H., Terao, Y. & Kinae, N. (2005). Mutat. Res. 585, 137–146.  CrossRef PubMed CAS Google Scholar
 First citationMurrell, B. (2006). McNair Scholars J. 10, Article 10.  Google Scholar
 First citationNakamura, S., Tezuka, Y., Ushiyama, A., Kawashima, C., Kitagawara, Y., Takahashi, K., Ohta, S. & Mashino, T. (2011). Toxicol. Lett. 203, 92–95.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationOkada, K. (1996). J. Mol. Struct. 380, 223–233.  CSD CrossRef CAS Web of Science Google Scholar
 First citationRichter, C. A., Birnbaum, L. S., Farabollini, F., Newbold, R. R., Rubin, B. S. & Talsness, C. E. (2007). Reprod. Toxicol. 24, 199–224.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationSakuyama, H., Endo, Y., Fujimoto, K. & Hatana, Y. (2003). J. Biosci. Bioeng. 96, 227–231.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. (2004). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationToyoizumi, T., Deguchi, Y., Masuda, S. & Kinae, N. (2007). Biosci. Biotechnol. Biochem. 72, 2118–2123.  CrossRef Google Scholar
 First citationVandenberg, L. N., Maffini, M. V., Sonnenschein, C., Rubin, B. S. & Soto, A. M. (2009). Endocr. Rev. 30, 75–95.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationWang, X. J., Gao, N. Y., Sun, X. F. & Xu, B. (2007). Huan Jing Ke Xue, 28, 2544–2549.  PubMed CAS Google Scholar
 First citationWang, J. L., Tang, C. P. & Chen, Y. J. (1982). Acta Cryst. B38, 2286–2288.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 67| Part 10| October 2011| Pages o2556-o2557
https://doi.org/10.1107/S1600536811035458
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