research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 72| Part 2| February 2016| Pages 257-260
doi:10.1107/S2056989016001432

Crystal structure of di­ethyl 2-acet­­oxy-2-[3-(4-nitro­phen­yl)-3-oxo-1-phenyl­prop­yl]malonate

CROSSMARK_Color_square_no_text.svg
Nóra Veronika May,a* Gyula Tamás Gál,a Zsolt Rapib and Péter Bakób

aInstitute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, H-1519 Budapest, POB 206, Hungary, and bDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1521 Budapest, POB 91, Hungary
*Correspondence e-mail: may.nora@ttk.mta.hu

Edited by G. Smith, Queensland University of Technology, Australia (Received 19 November 2015; accepted 22 January 2016; online 27 January 2016)

In the racemic title compound, C24H25NO9, the dihedral angle between the planes of the two benzene-ring systems is 80.16 (6)°, while the side-chain conformation is stabilized by a methyl­ene–carboxyl C—H⋯O hydrogen bond. Weak inter­molecular C—H⋯O hydrogen bonds form inversion dimers [graph set R22(16)] which are linked into chains extending along a. Further C—H⋯O hydrogen bonding extends the structure along b through cyclic R22(10) motifs. Although no π–π aromatic ring inter­actions are present in the structure, C—H⋯π ring inter­actions across c generate an overall three-dimensional supra­molecular structure.

CCDC reference: 1449223

1. Chemical context

The formation of C—C bonds by the Michael addition of the appropriate carboanionic reagents to α,β-unsaturated car­bonyl compounds is one of the most useful methods of remote functionalization in organic synthesis (Mather et al., 2006[Mather, B. D., Viswanathan, K., Miller, K. M. & Long, T. E. (2006). Prog. Polym. Sci. 31, 487-531.]; Little et al., 1995[Little, R. D., Masjedizadeh, M. R., Wallquist, O. & McLoughlin, J. I. (1995). Org. React. 47, 315-552.]). In particular, a much studied reaction is the conjugate addition of malonates to chalcones. Compounds with the chalcone backbone were reported to possess a wide range of biological activities, such as nematicidal, anti­fungal, anti­allergenic, anti­microbial, anti­cancer, anti­malarial and anti­feedant properties. Malonates are traditionally regarded as important materials for synthesizing the key inter­mediates of numerous active substances, but are rarely found as pharmacophores belonging to the target compounds (Lopez et al., 2001[Lopez, S. N., Castelli, M. V., Zacchino, S. A., Dominguez, J. N., Lobo, G., Charris-Charris, J., Cortes, J. C. G., Ribas, J. C., Devia, C., Rodriguez, A. M. & Enriz, R. D. (2001). Bioorg. Med. Chem. 9, 1999-2013.]; Chen et al., 2016[Chen, Z., Li, P., Hu, D., Dong, L., Pan, J., Luo, L., Zhang, W., Xue, W., Jin, L. & Song, B. (2016). Arab. J. Chem. In the press. doi: 10.1016/j. arabjc. 2015.05.003.]). Therefore, a catalytic version of the Michael addition of dialkyl malonates to chalcones in the presence of different catalysts has been studied extensively in recent years. Many phase-transfer-catalyzed methods that are simple and environmentally friendly have been developed for the Michael reaction (Shioiri, 1997[Shioiri, T. (1997). In Handbook of Phase-Transfer Catalysis, edited by Y. Sasson & R. Neumann. London: Blackie Academic and Professional.]). This new racemic compound was prepared in a phase-transfer reaction using a sugar-based crown ether as the catalyst (Rapi et al., 2016[Rapi, Z., Bakó, P., Grün, A., Nemcsók, T., Hessz, D., Kállay, M., Kubinyi, M. & Keglevich, G. (2016). Tetrahedron Asymmetry. In the press.]).

[Scheme 1]

2. Structural commentary

The mol­ecular structure of the racemic title compound is shown in Fig. 1[link]. In this mol­ecule, the C4 atom is a chiral centre, but no resolution occurred upon crystal preparation, the racemic mixture crystallizing in the centrosymmetric space group P21/n. The dihedral angle between the planes of the two benzene rings is 80.16 (6)° and the mol­ecular conformation is stabilized by an intra­molecular methyl­ene C5—H⋯O5 hydrogen bond (Table 1[link]).

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C7–C12 ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C5—H5A⋯O5 0.99 2.41 3.1403 (15) 130
C11—H11⋯O4i 0.95 2.54 3.2588 (16) 133
C12—H12⋯O6i 0.95 2.56 3.4879 (15) 165
C15—H15⋯O7ii 0.95 2.60 3.2038 (17) 122
C24—H24B⋯O8iii 0.98 2.47 3.402 (2) 158
C16—H16⋯Cgiv 0.95 2.81 3.6550 (14) 149
Symmetry codes: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+1, -y+1, -z+1; (iii) x-1, y, z; (iv) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].
[Figure 1]
Figure 1
The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

3. Supra­molecular features

Because of the numerous C=O acceptor groups and the lack of primary donor groups in the mol­ecule, the main inter­molecular inter­actions in the crystal are weak C—H⋯Ocarbox­yl hydrogen bonds (Table 1[link]), having H⋯O distances equal to or less than 2.6 Å. However, one of the four inter­actions (C24—H⋯O8iii; see Table 1[link] for hydrogen-bond geometry details and symmetry codes) involves a nitro O-atom acceptor. Inter­molecular C15—H⋯O7ii hydrogen bonds form centrosymmetric cyclic dimers (Fig. 2[link]) having the graph-set descriptor (Bernstein et al., 1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]) R22(16). These dimers are linked along the crystallographic a direction through C24—H⋯O8iii hydrogen bonds, forming a chain. These chains are further extended in the crystallographic b direction through C11—H⋯O4i and C12—H⋯O6i inter­actions, forming a cyclic motif with the graph-set descriptor of R22(10) (Fig. 3[link]). Despite the presence of two aromatic rings in the mol­ecule, there are no significant π–π inter­actions in the crystal lattice. This can be explained by the diverse chain system of the mol­ecule and, therefore, the steric preference of the C—H⋯O hydrogen bonds. However, there is a C16—H16⋯π inter­action across c with the C7–C12 nitro­phenyl ring (C⋯Cgiv = 2.81 Å and C—H⋯Cgiv = 149°; Cg is the centroid of the C7–C12 ring) (Fig. 4[link] and Table 1[link]), resulting in an overall three-dimensional supra­molecular structure. The relatively high calculated density (1.367 Mg m−3) and KPI index (Kitaigorodskii packing coefficient = 69.6%) (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) show efficient packing of the mol­ecule, resulting in no residual solvent-accessible voids.

[Figure 2]
Figure 2
A view of the column structure extending along the a axis, showing the C—H⋯O inter­actions as dashed lines.
[Figure 3]
Figure 3
A view of the column expansion along the b axis, showing the C—H⋯O inter­actions as dashed lines.
[Figure 4]
Figure 4
The arrangement of four mol­ecules, showing the C—H⋯Cg inter­actions (dashed lines).

4. Database survey

The structures of different derivatives of 1,2-di­phenyl­pentan-1-one, carrying methyl or nitrile substituents on the chiral C atom, have been reported, viz. Cambridge Structural Database (CSD; Groom & Allen, 2014[Groom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed. 53, 662-671.]) refcodes RULFIN [(S)-4-methyl-4-nitro-1,3-di­phenyl­penta­none; Bakó et al., 1997[Bakó, P., Szöllősy, A., Bombicz, P. & Tőke, L. (1997). Synlett, pp. 291-292.]], DULJOK (1,3-di­phenyl­butan-1-one; Bąkowicz & Turowska-Tyrk, 2010[Bąkowicz, J. & Turowska-Tyrk, I. (2010). Acta Cryst. C66, o29-o32.]) and LAPKEU (4-oxo-2,4-di­phenyl­butano­nitrile; Abdel-Aziz et al., 2012[Abdel-Aziz, A. A.-M., El-Azab, A. S., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o736.]). RULFIN and DULJOK crystallized in the chiral P212121 and Pca21 space groups, respectively, and LAPKEU crystallized as a racemic mixture in the centrosymmetric P21/c space group. Comparing the dihedral angles between the planes of the two benzene rings, the steric effect of the bulky substituents on atom C2 can be seen. This value is 62.5° for the methyl derivative (DULJOK) and 68.4° for the nitrile (LAPKEU), but significantly higher for the bulky meth­yl–nitro derivative (88.13°; RULFIN) or the title compound (80.2°).

5. Synthesis and crystallization

The title compound was synthesized by the reaction of 4′-nitro­chalcone [(E)-3-(4-nitro­phen­yl)-1-phenyl­prop-2-en-1-one] with diethyl 2-acet­oxy­malonate. The reaction was carried out in a solid/liquid two-phase system [Na2CO3/tetra­hydro­furan (THF)] in the presence of a gluco­pyran­oside-based crown ether catalyst. The compound was isolated by preparative thin-layer chromatography (TLC) (silica gel) in good yield. The structure of the compound was confirmed by 1H and 13C NMR and mass spectroscopy (m.p. 366–369 K). The details of the synthesis are presented in Rapi et al. (2016[Rapi, Z., Bakó, P., Grün, A., Nemcsók, T., Hessz, D., Kállay, M., Kubinyi, M. & Keglevich, G. (2016). Tetrahedron Asymmetry. In the press.]). Single crystals of the title compound suitable for X-ray diffraction analysis were obtained by crystallization from ethanol.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. All H atoms were located in difference electron-density maps. However, these atoms were included in the structure refinement at calculated positions, with C—H = 0.95–1.00 Å, and allowed to ride, with Uiso(H) = 1.2Ueq(C).

Table 2
Experimental details

Crystal data
Chemical formula C24H25NO9
Mr 471.46
Crystal system, space group Monoclinic, P21/n
Temperature (K) 103
a, b, c (Å) 11.0111 (7), 13.1762 (8), 15.8196 (9)
β (°) 93.802 (2)
V (Å3) 2290.1 (2)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.11
Crystal size (mm) 0.45 × 0.38 × 0.08
 
Data collection
Diffractometer R-AXIS RAPID
Absorption correction Empirical (NUMABS; Higashi, 2002[Higashi, T. (2002). NUMABS. Rigaku/MSC Inc., Tokyo, Japan.])
Tmin, Tmax 0.957, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections 67635, 7609, 6054
Rint 0.046
(sin θ/λ)max (Å−1) 0.735
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.128, 1.12
No. of reflections 7609
No. of parameters 310
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.49, −0.38
Computer programs: CrystalClear (Rigaku/MSC, 2008[Rigaku/MSC (2008). CrystalClear. Rigaku/MSC Inc., Tokyo, Japan.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]).

Supporting information

CCDC reference: 1449223

Crystal structure: contains datablocks I, header. DOI: 10.1107/S2056989016001432/zs2354sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989016001432/zs2354Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989016001432/zs2354Isup3.cml

checkCIF report


Chemical context top

The formation of C—C bonds by the Michael addition of the appropriate carboanionic reagents to α,β-unsaturated carbonyl compounds is one of the most useful methods of remote functionalization in organic synthesis (Mather et al., 2006; Little et al., 1995). In particular, a much studied reaction is the conjugate addition of malonates to chalcones. Compounds with the chalcone backbone were reported to possess a wide range of biological activities, such as nematicidal, anti­fungal, anti­allergenic, anti­microbial, anti­cancer, anti­malarial and anti­feedant properties. Malonates are traditionally regarded as important materials for synthesizing the key inter­mediates of numerous active substances, but are rarely found as pharmacophores belonging to the target compounds (Lopez et al., 2001; Chen et al., 2016). Therefore, a catalytic version of the Michael addition of di­alkyl malonates to chalcones in the presence of different catalysts has been studied extensively in recent years. Many phase-transfer-catalyzed methods that are simple and environmentally friendly have been developed for the Michael reaction (Shioiri, 1997). This new racemic compound was prepared in a phase-transfer reaction using a sugar-based crown ether as the catalyst (Rapi et al., 2016).

Structural commentary top

The molecular structure of the racemic title compound is shown in Fig. 1. In this molecule, the C4 atom is a chiral centre, but no resolution occurred upon crystal preparation, the racemic mixture crystallizing in the centrosymmetric space group P21/n. The dihedral angle between the planes of the two benzene rings is 80.16 (6)° and the molecular conformation is stabilized by an intra­molecular methyl­ene C5—H···O5 hydrogen bond (Table 2).

Supra­molecular features top

Because of the numerous C═O acceptor groups and the lack of primary donor groups in the molecule, the main inter­molecular inter­actions in the crystal are weak C—H···Ocarboxyl hydrogen bonds (Table 1), having an H···O distance equal to or less than 2.6 Å. However, one of the four inter­actions (C24—H···O8iii; see Table 2 for hydrogen-bond geometric details and symmetry codes) involves a nitro O-atom acceptor. Inter­molecular C15—H···O7ii hydrogen bonds form centrosymmetric cyclic dimers (Fig. 2) having the graph-set descriptor (Bernstein et al., 1995) R22(16). These dimers are linked along the crystallographic a direction through C24—H···O8iii hydrogen bonds, forming a chain. These chains are further extended in the crystallographic b direction through C11—H···O4i and C12—H···O6i inter­actions, forming a cyclic motif with the graph-set descriptor of R22(10) (Fig. 3). Despite the presence of two aromatic rings in the molecule, there are no significant π–π inter­actions in the crystal lattice. This can be explained by the diverse chain system of the molecule and, therefore, the steric preference of the C—H···O hydrogen bonds. However, there is a C16—H16···π inter­action across c with the C7–C12 nitro­phenyl ring (C···Cgiv = 2.81 Å and C—H···Cgiv = 149°; Cg is the centroid of the C7–C12 ring) (Fig. 4), resulting in an overall three-dimensional supra­molecular structure. The relatively high calculated density (1.367 Mg m−3) and K·P·I. index (Kitaigorodskii packing coefficient = 69.6%) (Spek, 2009) show efficient packing of the molecule resulting in no residual solvent-accessible voids.

Database survey top

The structures of different derivatives of 1,2-di­phenyl­pentan-1-one, carrying methyl or nitrile substituents on the chiral C atom, have been reported, viz. Cambridge Structural Database (CSD; Groom & Allen, 2014) refcodes RULFIN [(S)-4-methyl-4-nitro-1,3-di­phenyl­penta­none [Bakó et al., 1997], DULJOK (1,3-di­phenyl­butan-1-one; Bakowicz & Turowska-Tyrk, 2010) and LAPKEU (4-oxo-2,4-di­phenyl­butane­nitrile; Abdel-Aziz et al., 2012). RULFIN and DULJOK were crystallized in the chiral P212121 and Pca21 space groups, respectively, and LAPKEU crystallized as a racemic mixture in the centrosymmetric P21/c space group. Comparing the dihedral angles between the planes of the two benzene rings the steric effect of the bulky substituents on atom C2 can be seen. This value is 62.5° for the methyl derivative (DULJOK) and 68.4° for the nitrile (LAPKEU), but significantly higher for the bulky methyl–nitro derivative (88.13°; RULFIN) or the title compound (80.2°).

Synthesis and crystallization top

The title compound was synthesized by the reaction of 4'-nitro­chalcone [(E)-3-(4-nitro­phenyl)-1-phenyl­prop-2-en-1-one] with di­ethyl 2-acet­oxy­malonate. The reaction was carried out in a solid/liquid two-phase system [Na2CO3/tetra­hydro­furan (THF)] in the presence of a gluco­pyran­oside-based crown ether catalyst. The compound was isolated by preparative thin-layer chromatography (TLC) (silica gel) in good yield. The structure of the compound was confirmed by 1H and 13C NMR and mass spectroscopy (m.p. 366–369 K). The details of the synthesis are presented in Rapi et al. (2016). Single crystals of the title compound suitable for X-ray diffraction analysis were obtained by crystallization from ethanol.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. A l l H atoms were located in difference electron-density maps. However, these atoms were included in the structure refinement at calculated positions, with C—H = 0.95–1.00 Å, and allowed to ride, with Uiso(H) = 1.2Ueq(C).

Structure description top

The formation of C—C bonds by the Michael addition of the appropriate carboanionic reagents to α,β-unsaturated carbonyl compounds is one of the most useful methods of remote functionalization in organic synthesis (Mather et al., 2006; Little et al., 1995). In particular, a much studied reaction is the conjugate addition of malonates to chalcones. Compounds with the chalcone backbone were reported to possess a wide range of biological activities, such as nematicidal, anti­fungal, anti­allergenic, anti­microbial, anti­cancer, anti­malarial and anti­feedant properties. Malonates are traditionally regarded as important materials for synthesizing the key inter­mediates of numerous active substances, but are rarely found as pharmacophores belonging to the target compounds (Lopez et al., 2001; Chen et al., 2016). Therefore, a catalytic version of the Michael addition of di­alkyl malonates to chalcones in the presence of different catalysts has been studied extensively in recent years. Many phase-transfer-catalyzed methods that are simple and environmentally friendly have been developed for the Michael reaction (Shioiri, 1997). This new racemic compound was prepared in a phase-transfer reaction using a sugar-based crown ether as the catalyst (Rapi et al., 2016).

The molecular structure of the racemic title compound is shown in Fig. 1. In this molecule, the C4 atom is a chiral centre, but no resolution occurred upon crystal preparation, the racemic mixture crystallizing in the centrosymmetric space group P21/n. The dihedral angle between the planes of the two benzene rings is 80.16 (6)° and the molecular conformation is stabilized by an intra­molecular methyl­ene C5—H···O5 hydrogen bond (Table 2).

Because of the numerous C═O acceptor groups and the lack of primary donor groups in the molecule, the main inter­molecular inter­actions in the crystal are weak C—H···Ocarboxyl hydrogen bonds (Table 1), having an H···O distance equal to or less than 2.6 Å. However, one of the four inter­actions (C24—H···O8iii; see Table 2 for hydrogen-bond geometric details and symmetry codes) involves a nitro O-atom acceptor. Inter­molecular C15—H···O7ii hydrogen bonds form centrosymmetric cyclic dimers (Fig. 2) having the graph-set descriptor (Bernstein et al., 1995) R22(16). These dimers are linked along the crystallographic a direction through C24—H···O8iii hydrogen bonds, forming a chain. These chains are further extended in the crystallographic b direction through C11—H···O4i and C12—H···O6i inter­actions, forming a cyclic motif with the graph-set descriptor of R22(10) (Fig. 3). Despite the presence of two aromatic rings in the molecule, there are no significant π–π inter­actions in the crystal lattice. This can be explained by the diverse chain system of the molecule and, therefore, the steric preference of the C—H···O hydrogen bonds. However, there is a C16—H16···π inter­action across c with the C7–C12 nitro­phenyl ring (C···Cgiv = 2.81 Å and C—H···Cgiv = 149°; Cg is the centroid of the C7–C12 ring) (Fig. 4), resulting in an overall three-dimensional supra­molecular structure. The relatively high calculated density (1.367 Mg m−3) and K·P·I. index (Kitaigorodskii packing coefficient = 69.6%) (Spek, 2009) show efficient packing of the molecule resulting in no residual solvent-accessible voids.

The structures of different derivatives of 1,2-di­phenyl­pentan-1-one, carrying methyl or nitrile substituents on the chiral C atom, have been reported, viz. Cambridge Structural Database (CSD; Groom & Allen, 2014) refcodes RULFIN [(S)-4-methyl-4-nitro-1,3-di­phenyl­penta­none [Bakó et al., 1997], DULJOK (1,3-di­phenyl­butan-1-one; Bakowicz & Turowska-Tyrk, 2010) and LAPKEU (4-oxo-2,4-di­phenyl­butane­nitrile; Abdel-Aziz et al., 2012). RULFIN and DULJOK were crystallized in the chiral P212121 and Pca21 space groups, respectively, and LAPKEU crystallized as a racemic mixture in the centrosymmetric P21/c space group. Comparing the dihedral angles between the planes of the two benzene rings the steric effect of the bulky substituents on atom C2 can be seen. This value is 62.5° for the methyl derivative (DULJOK) and 68.4° for the nitrile (LAPKEU), but significantly higher for the bulky methyl–nitro derivative (88.13°; RULFIN) or the title compound (80.2°).

Synthesis and crystallization top

The title compound was synthesized by the reaction of 4'-nitro­chalcone [(E)-3-(4-nitro­phenyl)-1-phenyl­prop-2-en-1-one] with di­ethyl 2-acet­oxy­malonate. The reaction was carried out in a solid/liquid two-phase system [Na2CO3/tetra­hydro­furan (THF)] in the presence of a gluco­pyran­oside-based crown ether catalyst. The compound was isolated by preparative thin-layer chromatography (TLC) (silica gel) in good yield. The structure of the compound was confirmed by 1H and 13C NMR and mass spectroscopy (m.p. 366–369 K). The details of the synthesis are presented in Rapi et al. (2016). Single crystals of the title compound suitable for X-ray diffraction analysis were obtained by crystallization from ethanol.

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 2. A l l H atoms were located in difference electron-density maps. However, these atoms were included in the structure refinement at calculated positions, with C—H = 0.95–1.00 Å, and allowed to ride, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL2014/7.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A view of the column structure extending along the a axis, showing the C—H···O interactions as dashed lines.
[Figure 3] Fig. 3. A view of the column expansion along the b axis, showing the C—H···O interactions as dashed lines.
[Figure 4] Fig. 4. The arrangement of four molecules, showing the C—H···Cg interactions (dashed lines).
diethyl-2-acetoxy-2-(3-(4-nitrophenyl)3-oxo-1-phenylpropyl)malonate top
Crystal data top
C24H25NO9Dx = 1.367 Mg m−3
Mr = 471.46Melting point = 366–369 K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.0111 (7) ÅCell parameters from 39929 reflections
b = 13.1762 (8) Åθ = 3.0–31.5°
c = 15.8196 (9) ŵ = 0.11 mm−1
β = 93.802 (2)°T = 103 K
V = 2290.1 (2) Å3Block, colorless
Z = 40.45 × 0.38 × 0.08 mm
F(000) = 992
Data collection top
R-AXIS-RAPID
diffractometer		7609 independent reflections
Radiation source: Sealed Tube6054 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
Detector resolution: 10.0000 pixels mm-1θmax = 31.5°, θmin = 3.0°
dtprofit.ref scansh = −16→16
Absorption correction: empirical (using intensity measurements)
Higashi (2002). Numerical Absorption Correction: NUMABS		k = −19→19
Tmin = 0.957, Tmax = 0.979l = −23→23
67635 measured reflections
Refinement top
Refinement on F2Primary atom site location: difference Fourier map
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: difference Fourier map
wR(F2) = 0.128H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.0518P)2 + 0.9253P]
where P = (Fo2 + 2Fc2)/3
7609 reflections(Δ/σ)max = 0.001
310 parametersΔρmax = 0.49 e Å−3
0 restraintsΔρmin = −0.38 e Å−3
Crystal data top
C24H25NO9V = 2290.1 (2) Å3
Mr = 471.46Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.0111 (7) ŵ = 0.11 mm−1
b = 13.1762 (8) ÅT = 103 K
c = 15.8196 (9) Å0.45 × 0.38 × 0.08 mm
β = 93.802 (2)°
Data collection top
R-AXIS-RAPID
diffractometer		7609 independent reflections
Absorption correction: empirical (using intensity measurements)
Higashi (2002). Numerical Absorption Correction: NUMABS		6054 reflections with I > 2σ(I)
Tmin = 0.957, Tmax = 0.979Rint = 0.046
67635 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.128H-atom parameters constrained
S = 1.12Δρmax = 0.49 e Å−3
7609 reflectionsΔρmin = −0.38 e Å−3
310 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O30.16456 (8)0.30912 (6)0.25349 (6)0.01897 (17)
O50.26884 (8)0.41900 (7)0.14208 (6)0.02136 (18)
O60.21898 (8)0.56611 (7)0.20333 (6)0.02246 (18)
O20.14316 (8)0.54562 (6)0.36420 (6)0.02048 (18)
O40.01727 (9)0.37984 (8)0.16696 (6)0.0278 (2)
O10.01500 (8)0.41220 (7)0.35300 (7)0.0267 (2)
C110.67021 (11)0.06374 (9)0.29676 (8)0.0205 (2)
H110.6453−0.00320.28160.025*
C50.40905 (10)0.31827 (9)0.29982 (8)0.0177 (2)
H5B0.37670.24840.30360.021*
H5A0.41380.33510.23910.021*
C80.74760 (11)0.25968 (9)0.34224 (8)0.0211 (2)
H80.77330.32640.35760.025*
O70.56808 (9)0.39344 (8)0.38850 (7)0.0299 (2)
C40.32199 (10)0.39265 (9)0.33974 (7)0.0165 (2)
H40.36390.45990.34480.020*
C100.79207 (11)0.08750 (9)0.31234 (8)0.0194 (2)
N10.88210 (10)0.00521 (8)0.30793 (7)0.0236 (2)
O80.98968 (9)0.02854 (9)0.30729 (9)0.0407 (3)
C10.10634 (10)0.45486 (9)0.33559 (8)0.0186 (2)
C20.20283 (10)0.40756 (8)0.28145 (7)0.0167 (2)
O90.84527 (10)−0.08248 (8)0.30556 (8)0.0339 (2)
C160.23200 (12)0.30653 (10)0.59164 (8)0.0239 (2)
H160.21110.28840.64700.029*
C60.53495 (10)0.32257 (9)0.34362 (8)0.0192 (2)
C30.22914 (10)0.47531 (9)0.20474 (8)0.0179 (2)
C70.62319 (10)0.23832 (9)0.32841 (7)0.0180 (2)
C130.29301 (10)0.36000 (9)0.42848 (7)0.0180 (2)
C230.07300 (11)0.30567 (10)0.19098 (8)0.0220 (2)
C180.24448 (12)0.26431 (9)0.44386 (8)0.0231 (2)
H180.23210.21700.39880.028*
C140.31184 (11)0.42777 (9)0.49593 (8)0.0203 (2)
H140.34630.49250.48650.024*
C200.11540 (16)0.69755 (11)0.44259 (10)0.0331 (3)
H20C0.06750.73060.48480.040*
H20A0.10710.73580.38940.040*
H20B0.20120.69560.46330.040*
C90.83308 (11)0.18426 (10)0.33364 (8)0.0217 (2)
H90.91760.19830.34210.026*
C120.58535 (11)0.14101 (9)0.30400 (8)0.0200 (2)
H120.50120.12740.29220.024*
C240.05811 (13)0.20038 (11)0.15718 (10)0.0299 (3)
H24A0.13840.17110.14930.036*
H24C0.01030.20210.10270.036*
H24B0.01590.15880.19740.036*
C190.06994 (12)0.59136 (10)0.42759 (9)0.0252 (3)
H19A0.07810.55190.48090.030*
H19B−0.01690.59230.40700.030*
C170.21419 (13)0.23829 (10)0.52514 (9)0.0257 (3)
H170.18100.17320.53520.031*
C150.28063 (12)0.40142 (10)0.57657 (8)0.0229 (2)
H150.29260.44860.62170.027*
C210.28528 (14)0.47311 (10)0.06304 (8)0.0270 (3)
H21A0.34020.43390.02820.032*
H21B0.32330.54000.07570.032*
C220.16416 (16)0.48792 (13)0.01442 (10)0.0390 (4)
H22B0.17650.5225−0.03920.047*
H22C0.11120.52920.04800.047*
H22A0.12610.42170.00280.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0175 (4)0.0147 (4)0.0243 (4)−0.0015 (3)−0.0016 (3)−0.0012 (3)
O50.0267 (4)0.0191 (4)0.0185 (4)0.0018 (3)0.0032 (3)−0.0001 (3)
O60.0272 (4)0.0168 (4)0.0233 (4)0.0016 (3)0.0016 (3)0.0011 (3)
O20.0209 (4)0.0170 (4)0.0241 (4)0.0014 (3)0.0057 (3)−0.0016 (3)
O40.0223 (4)0.0271 (5)0.0331 (5)0.0028 (4)−0.0049 (4)−0.0010 (4)
O10.0201 (4)0.0263 (5)0.0343 (5)−0.0025 (3)0.0062 (4)−0.0022 (4)
C110.0201 (5)0.0181 (5)0.0232 (6)−0.0002 (4)0.0013 (4)−0.0003 (4)
C50.0156 (5)0.0168 (5)0.0205 (5)0.0010 (4)−0.0003 (4)−0.0020 (4)
C80.0174 (5)0.0205 (5)0.0249 (6)−0.0002 (4)−0.0010 (4)−0.0023 (5)
O70.0210 (4)0.0279 (5)0.0401 (6)0.0008 (4)−0.0030 (4)−0.0160 (4)
C40.0153 (5)0.0161 (5)0.0181 (5)0.0005 (4)0.0003 (4)−0.0011 (4)
C100.0189 (5)0.0207 (5)0.0186 (5)0.0036 (4)0.0019 (4)0.0006 (4)
N10.0219 (5)0.0233 (5)0.0257 (5)0.0054 (4)0.0012 (4)0.0010 (4)
O80.0191 (5)0.0328 (6)0.0699 (8)0.0054 (4)−0.0001 (5)−0.0033 (5)
C10.0160 (5)0.0170 (5)0.0226 (5)0.0022 (4)−0.0007 (4)0.0014 (4)
C20.0165 (5)0.0131 (5)0.0203 (5)−0.0006 (4)0.0004 (4)−0.0002 (4)
O90.0326 (5)0.0206 (4)0.0494 (6)0.0044 (4)0.0099 (5)0.0007 (4)
C160.0260 (6)0.0273 (6)0.0188 (5)0.0031 (5)0.0034 (4)0.0019 (5)
C60.0161 (5)0.0196 (5)0.0217 (5)0.0000 (4)0.0005 (4)−0.0022 (4)
C30.0154 (5)0.0180 (5)0.0201 (5)0.0002 (4)−0.0011 (4)0.0003 (4)
C70.0167 (5)0.0186 (5)0.0185 (5)0.0002 (4)−0.0005 (4)−0.0007 (4)
C130.0179 (5)0.0172 (5)0.0187 (5)0.0020 (4)−0.0001 (4)−0.0002 (4)
C230.0177 (5)0.0233 (6)0.0250 (6)−0.0025 (4)0.0003 (4)−0.0023 (5)
C180.0285 (6)0.0183 (5)0.0227 (6)−0.0003 (4)0.0034 (5)−0.0017 (5)
C140.0194 (5)0.0196 (5)0.0216 (5)0.0010 (4)−0.0015 (4)−0.0007 (4)
C200.0461 (9)0.0238 (6)0.0304 (7)−0.0004 (6)0.0110 (6)−0.0066 (5)
C90.0156 (5)0.0240 (6)0.0252 (6)0.0004 (4)−0.0017 (4)−0.0013 (5)
C120.0163 (5)0.0204 (5)0.0232 (6)−0.0006 (4)0.0003 (4)−0.0007 (4)
C240.0253 (6)0.0257 (6)0.0382 (8)−0.0053 (5)−0.0023 (5)−0.0080 (6)
C190.0257 (6)0.0235 (6)0.0273 (6)0.0041 (5)0.0088 (5)−0.0021 (5)
C170.0318 (7)0.0204 (6)0.0255 (6)−0.0013 (5)0.0060 (5)0.0024 (5)
C150.0234 (6)0.0252 (6)0.0198 (5)0.0020 (5)−0.0008 (4)−0.0036 (5)
C210.0379 (7)0.0244 (6)0.0191 (6)0.0015 (5)0.0058 (5)0.0016 (5)
C220.0491 (9)0.0432 (9)0.0232 (7)−0.0088 (7)−0.0089 (6)0.0033 (6)
Geometric parameters (Å, º) top
O1—C11.2000 (15)C16—C171.3879 (19)
O2—C11.3323 (14)C17—C181.3925 (19)
O2—C191.4581 (16)C19—C201.500 (2)
O3—C21.4251 (13)C21—C221.507 (2)
O3—C231.3653 (15)C23—C241.492 (2)
O4—C231.2021 (17)C4—H41.0000
O5—C31.3348 (15)C5—H5A0.9900
O5—C211.4610 (16)C5—H5B0.9900
O6—C31.2017 (15)C8—H80.9500
O7—C61.2144 (16)C9—H90.9500
O8—N11.2245 (15)C11—H110.9500
O9—N11.2243 (15)C12—H120.9500
N1—C101.4739 (16)C14—H140.9500
C1—C21.5400 (16)C15—H150.9500
C2—C31.5492 (16)C16—H160.9500
C2—C41.5653 (16)C17—H170.9500
C4—C51.5358 (16)C18—H180.9500
C4—C131.5222 (16)C19—H19A0.9900
C5—C61.5092 (16)C19—H19B0.9900
C6—C71.5051 (16)C20—H20A0.9800
C7—C81.4014 (16)C20—H20B0.9800
C7—C121.3948 (17)C20—H20C0.9800
C8—C91.3816 (17)C21—H21A0.9900
C9—C101.3866 (18)C21—H21B0.9900
C10—C111.3840 (17)C22—H22A0.9800
C11—C121.3918 (17)C22—H22B0.9800
C13—C141.3963 (17)C22—H22C0.9800
C13—C181.3970 (17)C24—H24A0.9800
C14—C151.3872 (18)C24—H24B0.9800
C15—C161.3870 (19)C24—H24C0.9800
C1—O2—C19115.78 (9)C4—C5—H5A109.00
C2—O3—C23116.36 (9)C4—C5—H5B109.00
C3—O5—C21115.44 (10)C6—C5—H5A109.00
O8—N1—O9123.73 (12)C6—C5—H5B109.00
O8—N1—C10118.02 (11)H5A—C5—H5B108.00
O9—N1—C10118.25 (11)C7—C8—H8120.00
O1—C1—O2125.68 (11)C9—C8—H8120.00
O1—C1—C2123.90 (11)C8—C9—H9121.00
O2—C1—C2110.28 (9)C10—C9—H9121.00
O3—C2—C1109.89 (9)C10—C11—H11121.00
O3—C2—C3110.37 (9)C12—C11—H11121.00
O3—C2—C4106.72 (9)C7—C12—H12120.00
C1—C2—C3111.98 (9)C11—C12—H12120.00
C1—C2—C4107.79 (9)C13—C14—H14120.00
C3—C2—C4109.93 (9)C15—C14—H14120.00
O5—C3—O6125.05 (12)C14—C15—H15120.00
O5—C3—C2110.42 (10)C16—C15—H15120.00
O6—C3—C2124.49 (11)C15—C16—H16120.00
C2—C4—C5111.07 (9)C17—C16—H16120.00
C2—C4—C13111.10 (9)C16—C17—H17120.00
C5—C4—C13111.94 (10)C18—C17—H17120.00
C4—C5—C6111.51 (10)C13—C18—H18120.00
O7—C6—C5121.90 (11)C17—C18—H18120.00
O7—C6—C7119.24 (10)O2—C19—H19A110.00
C5—C6—C7118.82 (10)O2—C19—H19B110.00
C6—C7—C8117.49 (10)C20—C19—H19A110.00
C6—C7—C12122.56 (10)C20—C19—H19B110.00
C8—C7—C12119.92 (11)H19A—C19—H19B109.00
C7—C8—C9120.36 (11)C19—C20—H20A109.00
C8—C9—C10118.18 (11)C19—C20—H20B109.00
N1—C10—C9118.60 (11)C19—C20—H20C109.00
N1—C10—C11118.19 (10)H20A—C20—H20B109.00
C9—C10—C11123.20 (11)H20A—C20—H20C109.00
C10—C11—C12117.92 (11)H20B—C20—H20C110.00
C7—C12—C11120.36 (11)O5—C21—H21A110.00
C4—C13—C14119.63 (10)O5—C21—H21B110.00
C4—C13—C18121.45 (10)C22—C21—H21A110.00
C14—C13—C18118.90 (11)C22—C21—H21B110.00
C13—C14—C15120.63 (11)H21A—C21—H21B108.00
C14—C15—C16120.38 (12)C21—C22—H22A109.00
C15—C16—C17119.37 (12)C21—C22—H22B109.00
C16—C17—C18120.66 (12)C21—C22—H22C109.00
C13—C18—C17120.06 (11)H22A—C22—H22B109.00
O2—C19—C20107.49 (11)H22A—C22—H22C109.00
O5—C21—C22110.13 (12)H22B—C22—H22C109.00
O3—C23—O4122.60 (12)C23—C24—H24A109.00
O3—C23—C24110.42 (11)C23—C24—H24B109.00
O4—C23—C24126.94 (12)C23—C24—H24C109.00
C2—C4—H4107.00H24A—C24—H24B109.00
C5—C4—H4108.00H24A—C24—H24C109.00
C13—C4—H4107.00H24B—C24—H24C109.00
C19—O2—C1—O15.55 (18)C1—C2—C3—O5−153.75 (9)
C19—O2—C1—C2−170.22 (10)C2—C4—C13—C14−109.31 (12)
C1—O2—C19—C20−172.46 (11)C5—C4—C13—C18−55.97 (14)
C23—O3—C2—C3−50.41 (13)C13—C4—C5—C6−69.13 (12)
C23—O3—C2—C173.57 (12)C2—C4—C5—C6166.04 (9)
C23—O3—C2—C4−169.83 (9)C5—C4—C13—C14125.88 (11)
C2—O3—C23—C24169.59 (10)C2—C4—C13—C1868.84 (14)
C2—O3—C23—O4−8.34 (17)C4—C5—C6—O7−17.48 (17)
C3—O5—C21—C22−78.91 (13)C4—C5—C6—C7164.86 (10)
C21—O5—C3—C2174.18 (10)C5—C6—C7—C8156.98 (11)
C21—O5—C3—O6−8.16 (17)O7—C6—C7—C12157.30 (12)
O8—N1—C10—C9−13.61 (18)C5—C6—C7—C12−24.98 (17)
O9—N1—C10—C11−12.60 (18)O7—C6—C7—C8−20.74 (17)
O9—N1—C10—C9166.02 (12)C8—C7—C12—C112.74 (18)
O8—N1—C10—C11167.78 (13)C12—C7—C8—C9−1.43 (18)
O2—C1—C2—C462.12 (12)C6—C7—C8—C9176.67 (11)
O1—C1—C2—C4−113.74 (13)C6—C7—C12—C11−175.26 (11)
O2—C1—C2—O3178.06 (9)C7—C8—C9—C10−0.93 (18)
O1—C1—C2—C3125.24 (13)C8—C9—C10—C112.08 (19)
O2—C1—C2—C3−58.90 (13)C8—C9—C10—N1−176.45 (11)
O1—C1—C2—O32.19 (16)C9—C10—C11—C12−0.80 (19)
O3—C2—C3—O5−30.98 (12)N1—C10—C11—C12177.74 (11)
C1—C2—C4—C5162.98 (9)C10—C11—C12—C7−1.63 (18)
C1—C2—C4—C1337.68 (12)C4—C13—C14—C15176.90 (11)
O3—C2—C3—O6151.34 (11)C18—C13—C14—C15−1.30 (18)
C4—C2—C3—O6−91.21 (13)C4—C13—C18—C17−177.30 (11)
C3—C2—C4—C13159.98 (9)C14—C13—C18—C170.86 (18)
O3—C2—C4—C13−80.32 (11)C13—C14—C15—C161.06 (19)
C3—C2—C4—C5−74.72 (11)C14—C15—C16—C17−0.4 (2)
C4—C2—C3—O586.48 (11)C15—C16—C17—C18−0.1 (2)
O3—C2—C4—C544.98 (12)C16—C17—C18—C13−0.2 (2)
C1—C2—C3—O628.57 (16)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C7–C12 ring.
D—H···AD—HH···AD···AD—H···A
C5—H5A···O50.992.413.1403 (15)130
C11—H11···O4i0.952.543.2588 (16)133
C12—H12···O6i0.952.563.4879 (15)165
C15—H15···O7ii0.952.603.2038 (17)122
C24—H24B···O8iii0.982.473.402 (2)158
C16—H16···Cgiv0.952.813.6550 (14)149
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z; (iv) x−1/2, −y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C7–C12 ring.
D—H···AD—HH···AD···AD—H···A
C5—H5A···O50.992.413.1403 (15)130
C11—H11···O4i0.952.543.2588 (16)133
C12—H12···O6i0.952.563.4879 (15)165
C15—H15···O7ii0.952.603.2038 (17)122
C24—H24B···O8iii0.982.473.402 (2)158
C16—H16···Cgiv0.952.813.6550 (14)149
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z; (iv) x−1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC24H25NO9
Mr471.46
Crystal system, space groupMonoclinic, P21/n
Temperature (K)103
a, b, c (Å)11.0111 (7), 13.1762 (8), 15.8196 (9)
β (°) 93.802 (2)
V (Å3)2290.1 (2)
Z4
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.45 × 0.38 × 0.08
Data collection
DiffractometerR-AXIS-RAPID
Absorption correctionEmpirical (using intensity measurements)
Higashi (2002). Numerical Absorption Correction: NUMABS
Tmin, Tmax0.957, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections		67635, 7609, 6054
Rint0.046
(sin θ/λ)max (Å−1)0.735
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.128, 1.12
No. of reflections7609
No. of parameters310
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.49, −0.38

Computer programs: CrystalClear (Rigaku/MSC, 2008), CrystalClear, SHELXS97 (Sheldrick, 2008), SHELXL2014/7 (Sheldrick, 2015), Mercury (Macrae et al., 2006), SHELXL2014/7.

 

Acknowledgements

This work was supported financially by the Hungarian Scientific Research Found (OTKA K No. 115762 and PD No. 112166) and the New Széchenyi Development Plan (TÁMOP-4.2.1/B-09/1/KMR-2010-0002).

References

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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 72| Part 2| February 2016| Pages 257-260
doi:10.1107/S2056989016001432
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