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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 1| January 2011| Page o78
https://doi.org/10.1107/S1600536810050890

Di­methyl (E)-2-(N-phenyl­acetamido)­but-2-enedioate

Shui Liang Guo,a Chen Fua* and Ting Bin Wena

aDepartment of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, People's Republic of China
*Correspondence e-mail: chem826@hotmail.com

(Received 28 November 2010; accepted 4 December 2010; online 11 December 2010)

The title compound, C14H15NO5, was obtained from the reaction of acetanilide with dimethyl acetyl­enedicarboxyl­ate in the presence of potassium carbonate. The C=C double bond adopts an E configuration and the geometry around the amide N atom is almost planar rather than pyramidal (mean deviation of 0.0032 Å from the C3N plane). The packing of the mol­ecules in the crystal structure is stabilized by inter­molecular C—H⋯O hydrogen bonds.

Related literature

For background to the hydro­amidation of alkynes, see: Severin & Doye (2007)[Severin, R. & Doye, S. (2007). Chem. Soc. Rev. 36, 1407-1420.]; Goossen et al. (2005[Goossen, J., Rauhaus, J. E. & Deng, G. (2005). Angew. Chem. Int. Ed. 44, 4042-4045.]); Cacchi & Fabrizi (2005)[Cacchi, S. & Fabrizi, G. (2005). Chem. Rev. 105, 2873-2920.]; For structurally related compounds, see: Kawahara et al. (1989[Kawahara, N., Shimori, T. & Takayanagi, H. (1989). J. Heterocycl. Chem. 26, 847-852.]); Penney et al. (1995[Penney, J., VanderLende, D. D., Boncella, J. M. & Abboud, K. A. (1995). Acta Cryst. C51, 2269-2271.]); Yet et al. (2003[Yet, L. F. (2003). Chem. Rev. 103, 4283-4306.]); Hua et al. (2003[Hua, J., Leger, J. M. & Dolain, C. (2003). Tetrahedron, 59, 8365-8374.]).

[Scheme 1]

Experimental

Crystal data

  • C14H15NO5

  • Mr = 277.27

  • Monoclinic, P 21 /n

  • a = 9.7920 (5) Å

  • b = 12.1917 (4) Å

  • c = 12.2281 (6) Å

  • β = 112.629 (6)°

  • V = 1347.42 (11) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 173 K

  • 0.15 × 0.12 × 0.10 mm
Data collection

  • Oxford Diffraction Gemini S Ultra diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.885, Tmax = 1.000

  • 7263 measured reflections

  • 3009 independent reflections

  • 2415 reflections with I > 2σ(I)

  • Rint = 0.029
Refinement

  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.091

  • S = 1.00

  • 3009 reflections

  • 181 parameters

  • H-atom parameters constrained

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C4—H4C⋯O3i 0.96 2.53 3.0831 (16) 117
C14—H14A⋯O3ii 0.93 2.57 3.2016 (15) 125
C12—H12A⋯O5iii 0.93 2.51 3.3073 (15) 145
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) -x+1, -y, -z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810050890/zl2334sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050890/zl2334Isup2.hkl

checkCIF report


Comment top

Hydroamidation of alkynes has proved to be an effective approach to construct enamides (Severin & Doye, 2007; Goossen et al. 2005; Cacchi & Fabrizi 2005), which are important substructures often found in natural products and synthetic drugs (Yet et al. 2003). In our studies on the reaction of dimethyl acetylenedicarboxylate with acetanilide in the presence of potassium carbonate, the title compound was formed via base mediated hydroamidation.

An X-ray diffraction study has been carried out to determine the structure (Fig. 1). The C=C double bond adopts an E configuration. The geometry around the amide N atom is planar rather than pyramidal, as reflected by the small mean deviation of 0.0032 Å from the least-squares plane defined by the four constituent atoms N1, C2, C7 and C11, which is probably due to the large degree of conjugation between the amide N atom and the adjacent acetyl group (the maximium deviation from the least-squares plane defined by N1, C2, C7, C11 and O5 is 0.0956 (9) Å for N1) (Penney, et al. 1995). The C1-C2 double bond is slightly tilted against one ester group with a dihedral angle of only 9.10 (21)° between the (C2, C1, C3) plane and the (C1, C3, O1, O2) plane, but it is tilted against the other ester group with a dihedral angle of 80.25 (4)° between the (C1, C2, C5) plane and the (C2, C5, O3, O4) plane. The dihedral angle of the double bond plane (C1, C2, N1) with respect to the amide group plane (C2, N1, C7, C11) is 23.97 (18) °. The structural features of the title compound agree well with that of similar compounds reported in literature (Kawahara et al. 1989; Hua et al. 2003).

The packing of molecules in the crystal structure is stabilized by non-classical intermolecular C—H···O hydrogen bonds (Fig. 2, Table 1). The intermolecular hydrogen bonding interactions between O3 atom of the ester group and methyl C-H (C4—H4C···O3i) as well as the aromatic C-H (C14—H14A···O3ii) form a 2-D networks parallel to the ac plane, which is further cross-linked by a hydrogen bond between O5 of the other ester group and an aromatic C-H (C12—H12A···O5iii) to give a 3-D hydrogen bonding network (Symmetry codes: (i) x-1/2,-y+1/2,z-1/2; (ii) x+1/2,-y+1/2,z-1/2; (iii) -x+1,-y,-z).

Related literature top

For background to the hydroamidation of alkynes, see: Severin & Doye (2007); Goossen et al. (2005); Cacchi & Fabrizi (2005); For structurally related compounds, see: Kawahara et al. (1989); Penney et al. (1995); Yet et al. (2003); Hua et al. (2003).

Experimental top

To a solution of acetanilide (0.27 g, 2.00 mmol) and dimethyl acetylenedicarboxylate (0.29 g, 2.04 mmol) in toluene (10 ml), potassium carbonate (0.57 g, 4.13 mmol) was added at room temperature. The mixture was then refluxed for 12 h under an atmosphere of dinitrogen. After concentration, the residue was purified by flash chromatography (ethyl acetate/petroleum = 1:2) to give the product as a white solid. Yield: 0.37 g, 67.2%. 1H NMR (400 MHz, CDCl3): δ 7.60-7.24 (m, 5 H, Ar), 5 .85 (s, 1 H, CH), 3.79 (s, 3 H, OCH3), 3.58 (s, 3 H, OCH3), 1.96 (s, 3 H, CH3) ppm; 13C NMR (101 MHz, CDCl3): δ 168.6, 166.4, 166.1, 152.3, 135.9, 129.6, 123.2, 121.5, 107.5, 52.8, 52.0, 20.8 ppm. ESI-MS: 300.3 [M+Na]+. Single crystals were obtained by slow evaporation of a solution in dichloromethane/hexane.

Refinement top

One of the reflections, (-5 3 5), was found to be inconsistent with an I(obs) value more that 10 times SigmaW diffeent from I(calc). Inspection of the frame showed that the reflection was located at the frame edge and it was thus omitted from the refinement.

All non-hydrogen atoms were refined anisotropically. The hydrogen atoms were positioned geometrically (C—H = 0.93, 0.93 or 0.96Å for phenyl, methylene or methyl H atoms respectively) and included in the refinement in the riding model approximation. The displacement parameters of vinyl and phenyl H atoms were set to 1.2Ueq(C), while those of methyl H atoms were set to 1.5Ueq(C). In the final Fourier map the highest peak is 0.72 Å from atom H8A and the deepest hole is 0.59 Å from atom C8.

Structure description top

Hydroamidation of alkynes has proved to be an effective approach to construct enamides (Severin & Doye, 2007; Goossen et al. 2005; Cacchi & Fabrizi 2005), which are important substructures often found in natural products and synthetic drugs (Yet et al. 2003). In our studies on the reaction of dimethyl acetylenedicarboxylate with acetanilide in the presence of potassium carbonate, the title compound was formed via base mediated hydroamidation.

An X-ray diffraction study has been carried out to determine the structure (Fig. 1). The C=C double bond adopts an E configuration. The geometry around the amide N atom is planar rather than pyramidal, as reflected by the small mean deviation of 0.0032 Å from the least-squares plane defined by the four constituent atoms N1, C2, C7 and C11, which is probably due to the large degree of conjugation between the amide N atom and the adjacent acetyl group (the maximium deviation from the least-squares plane defined by N1, C2, C7, C11 and O5 is 0.0956 (9) Å for N1) (Penney, et al. 1995). The C1-C2 double bond is slightly tilted against one ester group with a dihedral angle of only 9.10 (21)° between the (C2, C1, C3) plane and the (C1, C3, O1, O2) plane, but it is tilted against the other ester group with a dihedral angle of 80.25 (4)° between the (C1, C2, C5) plane and the (C2, C5, O3, O4) plane. The dihedral angle of the double bond plane (C1, C2, N1) with respect to the amide group plane (C2, N1, C7, C11) is 23.97 (18) °. The structural features of the title compound agree well with that of similar compounds reported in literature (Kawahara et al. 1989; Hua et al. 2003).

The packing of molecules in the crystal structure is stabilized by non-classical intermolecular C—H···O hydrogen bonds (Fig. 2, Table 1). The intermolecular hydrogen bonding interactions between O3 atom of the ester group and methyl C-H (C4—H4C···O3i) as well as the aromatic C-H (C14—H14A···O3ii) form a 2-D networks parallel to the ac plane, which is further cross-linked by a hydrogen bond between O5 of the other ester group and an aromatic C-H (C12—H12A···O5iii) to give a 3-D hydrogen bonding network (Symmetry codes: (i) x-1/2,-y+1/2,z-1/2; (ii) x+1/2,-y+1/2,z-1/2; (iii) -x+1,-y,-z).

For background to the hydroamidation of alkynes, see: Severin & Doye (2007); Goossen et al. (2005); Cacchi & Fabrizi (2005); For structurally related compounds, see: Kawahara et al. (1989); Penney et al. (1995); Yet et al. (2003); Hua et al. (2003).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom-labelling scheme, showing 30% probability displacement ellipoids.
[Figure 2] Fig. 2. The packing of the molecules, viewed down the b axis. The C—H···O hydrogen bond interactions are shown as dashed lines.
Dimethyl (E)-2-(N-phenylacetamido)but-2-enedioate top
Crystal data top
C14H15NO5F(000) = 584
Mr = 277.27Dx = 1.367 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4186 reflections
a = 9.7920 (5) Åθ = 2.8–29.0°
b = 12.1917 (4) ŵ = 0.11 mm−1
c = 12.2281 (6) ÅT = 173 K
β = 112.629 (6)°Block, colorless
V = 1347.42 (11) Å30.15 × 0.12 × 0.10 mm
Z = 4
Data collection top
Oxford Diffraction Gemini S Ultra
diffractometer		3009 independent reflections
Radiation source: Enhance (Mo) X-ray Source2415 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 16.1930 pixels mm-1θmax = 27.5°, θmin = 2.8°
ω scansh = −12→12
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2008)		k = −15→10
Tmin = 0.885, Tmax = 1.000l = −14→15
7263 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.058P)2]
where P = (Fo2 + 2Fc2)/3
3009 reflections(Δ/σ)max = 0.001
181 parametersΔρmax = 0.24 e Å−3
0 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C14H15NO5V = 1347.42 (11) Å3
Mr = 277.27Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.7920 (5) ŵ = 0.11 mm−1
b = 12.1917 (4) ÅT = 173 K
c = 12.2281 (6) Å0.15 × 0.12 × 0.10 mm
β = 112.629 (6)°
Data collection top
Oxford Diffraction Gemini S Ultra
diffractometer		3009 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2008)		2415 reflections with I > 2σ(I)
Tmin = 0.885, Tmax = 1.000Rint = 0.029
7263 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.091H-atom parameters constrained
S = 1.00Δρmax = 0.24 e Å−3
3009 reflectionsΔρmin = −0.21 e Å−3
181 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O10.35048 (9)0.34762 (7)0.14129 (7)0.0233 (2)
N10.65965 (10)0.10602 (8)0.11896 (8)0.0173 (2)
C10.50153 (12)0.26233 (10)0.05139 (10)0.0184 (2)
H1A0.54260.2750−0.00450.022*
O20.36589 (9)0.41845 (7)−0.02353 (7)0.0233 (2)
C20.54018 (12)0.17090 (9)0.11658 (10)0.0166 (2)
O30.53999 (10)0.14493 (7)0.30872 (7)0.0265 (2)
C30.39784 (12)0.34379 (9)0.06335 (10)0.0184 (2)
O40.33137 (9)0.10799 (7)0.15035 (7)0.0211 (2)
C40.27339 (14)0.50801 (10)−0.01660 (12)0.0268 (3)
H4A0.25620.5569−0.08210.040*
H4B0.32180.54700.05630.040*
H4C0.18060.4797−0.01940.040*
O50.56257 (9)−0.04796 (7)0.16290 (8)0.0233 (2)
C50.47167 (13)0.13911 (9)0.20343 (10)0.0185 (3)
C60.26254 (15)0.07359 (11)0.22997 (12)0.0295 (3)
H6A0.16180.05290.18500.044*
H6B0.26460.13300.28210.044*
H6C0.31540.01200.27570.044*
C70.66568 (12)−0.00447 (9)0.14735 (10)0.0179 (2)
C80.80390 (13)−0.06526 (11)0.15872 (11)0.0251 (3)
H8A0.7954−0.14050.17830.038*
H8B0.8875−0.03240.22010.038*
H8C0.8171−0.06170.08500.038*
C110.77404 (12)0.15731 (9)0.08915 (10)0.0167 (2)
C120.77754 (13)0.14120 (10)−0.02186 (10)0.0195 (3)
H12A0.70620.0980−0.07780.023*
C130.88875 (13)0.19028 (10)−0.04866 (11)0.0224 (3)
H13A0.89310.1790−0.12250.027*
C140.99298 (13)0.25583 (10)0.03413 (11)0.0247 (3)
H14A1.06730.28870.01590.030*
C150.98695 (13)0.27261 (10)0.14413 (11)0.0240 (3)
H15A1.05680.31730.19930.029*
C160.87727 (13)0.22307 (10)0.17251 (11)0.0208 (3)
H16A0.87330.23390.24650.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0234 (5)0.0234 (5)0.0264 (5)0.0029 (4)0.0133 (4)−0.0002 (4)
N10.0167 (5)0.0172 (5)0.0206 (5)0.0008 (4)0.0101 (4)0.0014 (4)
C10.0176 (5)0.0211 (6)0.0188 (6)−0.0008 (5)0.0094 (5)−0.0001 (5)
O20.0258 (5)0.0194 (4)0.0259 (5)0.0052 (4)0.0112 (4)0.0038 (4)
C20.0147 (5)0.0190 (6)0.0166 (6)−0.0013 (4)0.0065 (4)−0.0031 (4)
O30.0285 (5)0.0340 (5)0.0187 (4)0.0051 (4)0.0111 (4)−0.0002 (4)
C30.0147 (5)0.0179 (6)0.0209 (6)−0.0038 (4)0.0049 (5)−0.0015 (5)
O40.0193 (4)0.0218 (4)0.0269 (5)−0.0009 (3)0.0140 (4)0.0020 (3)
C40.0282 (7)0.0187 (6)0.0326 (7)0.0055 (5)0.0106 (5)0.0020 (5)
O50.0236 (4)0.0204 (4)0.0297 (5)−0.0009 (4)0.0145 (4)0.0033 (4)
C50.0195 (6)0.0160 (6)0.0228 (6)0.0032 (4)0.0113 (5)0.0002 (5)
C60.0331 (7)0.0262 (7)0.0417 (8)0.0001 (6)0.0284 (6)0.0036 (6)
C70.0207 (6)0.0190 (6)0.0147 (5)0.0009 (5)0.0077 (4)0.0009 (4)
C80.0245 (6)0.0220 (6)0.0308 (7)0.0055 (5)0.0130 (5)0.0076 (5)
C110.0161 (6)0.0156 (5)0.0207 (6)0.0033 (4)0.0097 (5)0.0032 (5)
C120.0185 (6)0.0200 (6)0.0204 (6)−0.0011 (5)0.0079 (5)−0.0011 (5)
C130.0234 (6)0.0258 (6)0.0222 (6)0.0001 (5)0.0134 (5)0.0024 (5)
C140.0194 (6)0.0241 (6)0.0336 (7)−0.0012 (5)0.0135 (5)0.0070 (5)
C150.0187 (6)0.0211 (6)0.0292 (7)−0.0029 (5)0.0059 (5)−0.0017 (5)
C160.0204 (6)0.0212 (6)0.0207 (6)0.0021 (5)0.0078 (5)−0.0006 (5)
Geometric parameters (Å, º) top
O1—C31.2106 (14)C6—H6B0.9600
N1—C71.3867 (15)C6—H6C0.9600
N1—C21.4031 (14)C7—C81.5019 (16)
N1—C111.4466 (14)C8—H8A0.9600
C1—C21.3376 (16)C8—H8B0.9600
C1—C31.4672 (16)C8—H8C0.9600
C1—H1A0.9300C11—C161.3823 (16)
O2—C31.3413 (14)C11—C121.3849 (16)
O2—C41.4418 (14)C12—C131.3878 (15)
C2—C51.5088 (15)C12—H12A0.9300
O3—C51.2030 (14)C13—C141.3820 (18)
O4—C51.3290 (14)C13—H13A0.9300
O4—C61.4432 (13)C14—C151.3841 (18)
C4—H4A0.9600C14—H14A0.9300
C4—H4B0.9600C15—C161.3876 (16)
C4—H4C0.9600C15—H15A0.9300
O5—C71.2183 (14)C16—H16A0.9300
C6—H6A0.9600
C7—N1—C2120.51 (9)H6B—C6—H6C109.5
C7—N1—C11121.36 (9)O5—C7—N1120.25 (10)
C2—N1—C11118.12 (9)O5—C7—C8122.84 (11)
C2—C1—C3123.55 (10)N1—C7—C8116.91 (10)
C2—C1—H1A118.2C7—C8—H8A109.5
C3—C1—H1A118.2C7—C8—H8B109.5
C3—O2—C4115.32 (9)H8A—C8—H8B109.5
C1—C2—N1121.65 (10)C7—C8—H8C109.5
C1—C2—C5122.21 (10)H8A—C8—H8C109.5
N1—C2—C5115.69 (9)H8B—C8—H8C109.5
O1—C3—O2123.64 (10)C16—C11—C12121.21 (10)
O1—C3—C1126.44 (11)C16—C11—N1118.84 (10)
O2—C3—C1109.87 (10)C12—C11—N1119.95 (10)
C5—O4—C6114.63 (10)C11—C12—C13119.20 (11)
O2—C4—H4A109.5C11—C12—H12A120.4
O2—C4—H4B109.5C13—C12—H12A120.4
H4A—C4—H4B109.5C14—C13—C12120.11 (11)
O2—C4—H4C109.5C14—C13—H13A119.9
H4A—C4—H4C109.5C12—C13—H13A119.9
H4B—C4—H4C109.5C13—C14—C15120.12 (11)
O3—C5—O4125.75 (11)C13—C14—H14A119.9
O3—C5—C2121.56 (11)C15—C14—H14A119.9
O4—C5—C2112.68 (10)C14—C15—C16120.35 (11)
O4—C6—H6A109.5C14—C15—H15A119.8
O4—C6—H6B109.5C16—C15—H15A119.8
H6A—C6—H6B109.5C11—C16—C15119.00 (11)
O4—C6—H6C109.5C11—C16—H16A120.5
H6A—C6—H6C109.5C15—C16—H16A120.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4C···O3i0.962.533.0831 (16)117
C14—H14A···O3ii0.932.573.2016 (15)125
C12—H12A···O5iii0.932.513.3073 (15)145
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x+1/2, −y+1/2, z−1/2; (iii) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formulaC14H15NO5
Mr277.27
Crystal system, space groupMonoclinic, P21/n
Temperature (K)173
a, b, c (Å)9.7920 (5), 12.1917 (4), 12.2281 (6)
β (°) 112.629 (6)
V (Å3)1347.42 (11)
Z4
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.15 × 0.12 × 0.10
Data collection
DiffractometerOxford Diffraction Gemini S Ultra
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2008)
Tmin, Tmax0.885, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		7263, 3009, 2415
Rint0.029
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.091, 1.00
No. of reflections3009
No. of parameters181
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.24, −0.21

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4C···O3i0.962.533.0831 (16)116.8
C14—H14A···O3ii0.932.573.2016 (15)125.2
C12—H12A···O5iii0.932.513.3073 (15)144.6
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x+1/2, −y+1/2, z−1/2; (iii) −x+1, −y, −z.
 

Acknowledgements

The authors acknowledge the financial support from the Young Talent Project of the Department of Science & Technology of Fujian Province (grant No. 2007F3095).

References

First citationCacchi, S. & Fabrizi, G. (2005). Chem. Rev. 105, 2873–2920.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationGoossen, J., Rauhaus, J. E. & Deng, G. (2005). Angew. Chem. Int. Ed. 44, 4042–4045.  Web of Science CrossRef CAS Google Scholar
 First citationHua, J., Leger, J. M. & Dolain, C. (2003). Tetrahedron, 59, 8365–8374.  Web of Science CrossRef Google Scholar
 First citationKawahara, N., Shimori, T. & Takayanagi, H. (1989). J. Heterocycl. Chem. 26, 847–852.  CrossRef CAS Google Scholar
 First citationOxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
 First citationPenney, J., VanderLende, D. D., Boncella, J. M. & Abboud, K. A. (1995). Acta Cryst. C51, 2269–2271.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationSeverin, R. & Doye, S. (2007). Chem. Soc. Rev. 36, 1407–1420.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationYet, L. F. (2003). Chem. Rev. 103, 4283–4306.  Web of Science CrossRef PubMed CAS Google Scholar

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ISSN: 2056-9890
Volume 67| Part 1| January 2011| Page o78
https://doi.org/10.1107/S1600536810050890
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