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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 64| Part 12| December 2008| Page o2371
doi:10.1107/S1600536808036982

(Z)-Ethyl 3-(2,4-di­fluoro­anilino)-2-(4-meth­oxy­phen­yl)acrylate

Zhu-Ping Xiaoa* and He-Ying Xiaoa

aCollege of Chemistry & Chemical Engineering, Jishou University, Jishou 416000, People's Republic of China
*Correspondence e-mail: xiaozhuping2005@163.com

(Received 17 October 2008; accepted 10 November 2008; online 20 November 2008)

The title compound, C18H17F2NO3, consists of three individually planar subunits, namely two benzene rings and one amino­acrylate group. The amino­acrylate group forms dihedral angles of 5.92 (7) and 50.21 (6)° with the difluoro and methoxy benzene rings, respectively. The dihedral angle between the two benzene rings is 55.25 (7)°. The mol­ecules exhibit intra­molecular N—H⋯O and N—H⋯F inter­actions and form a three-dimensional network via inter­molecular C—H⋯O and C—H⋯π hydrogen bonds.

Related literature

For general background, see: Xiao, Fang et al. (2008[Xiao, Z.-P., Fang, R.-Q., Li, H.-Q., Shi, L., Xue, J.-Y., Zheng, Y. & Zhu, H.-L. (2008). Eur. J. Med. Chem. 43, 1828-1836.]); Xiao, Li et al. (2008[Xiao, Z.-P., Li, H.-Q., Xue, J.-Y., Shi, L. & Zhu, H.-L. (2008). Synth. Commun. 38, 525-529.]); Xiao, Xue et al. (2007[Xiao, Z.-P., Xue, J.-Y., Tan, S.-H., Li, H.-Q. & Zhu, H.-L. (2007). Bioorg. Med. Chem. 15, 4212-4219.]). For related structures, see: Xiao, Li, Shi et al. (2008[Xiao, Z.-P., Li, H.-Q., Shi, L., Lv, P.-C., Song, Z.-C. & Zhu, H.-L. (2008). ChemMedChem, 3, 1077-1083.]); Xiao, Lv et al. (2008[Xiao, Z.-P., Lv, P.-C., Xu, S.-P., Zhu, T.-T. & Zhu, H.-L. (2008). ChemMedChem, 3, 1516-1519.]); Xiao, Fang et al. (2007[Xiao, Z.-P., Fang, R.-Q., Shi, L., Ding, H., Xu, C. & Zhu, H.-L. (2007). Can. J. Chem. 85, 951-957.]).

[Scheme 1]

Experimental

Crystal data

  • C18H17F2NO3

  • Mr = 333.33

  • Monoclinic, P 21 /c

  • a = 17.295 (4) Å

  • b = 7.2940 (15) Å

  • c = 14.233 (3) Å

  • β = 113.73 (3)°

  • V = 1643.7 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 298 (2) K

  • 0.30 × 0.20 × 0.10 mm
Data collection

  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.969, Tmax = 0.989

  • 3108 measured reflections

  • 2974 independent reflections

  • 1889 reflections with I > 2σ(I)

  • Rint = 0.016
Refinement

  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.156

  • S = 1.02

  • 2974 reflections

  • 224 parameters

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

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C6—H6⋯O1i 0.93 2.51 3.280 (3) 140
C18—H18C⋯Cg1ii 0.96 2.92 3.631 132
N1—H1⋯F1 0.88 (2) 2.31 (2) 2.678 (2) 105.0 (18)
N1—H1⋯O1 0.88 (2) 2.02 (2) 2.678 (3) 131 (2)
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) -x+1, -y-1, -z+1. Cg1 is the centroid of C7–C12 ring.

Data collection: CAD-4 Software (Enraf–Nonius, 1989[Enraf-Nonius. (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036982/bq2102sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808036982/bq2102Isup2.hkl

checkCIF report


Comment top

An enamine, a tautomer of a Schiff base, shows a high similarity to the corresponding Schiff base in chemical structure which shows diverse biological activities. Our recent work affirmed that enamine, like Schiff base, exhibited high antibacterial activity (Xiao, Xue et al., 2007; Xiao, Fang et al., 2008; Xiao, Li et al., 2008). Meanwhile, an enamine is the key mediate for anticancer agents, 3-arylquinolone and 3-arylquinoline (Xiao, Li et al. 2008; Xiao, Lv et al., 2008; Xiao, Fang et al.,2008). We herein report the crystal structure of the title compound, (I), an enamine.

As shown in Fig. 1, (I) is structurally divided into three subunits, and each moiety forms a plane, namely, C1 to C6 forms a plane with the mean deviation of 0.0015 Å, defined as plane I; C7 to C12 forms a plane with the mean deviation of 0.0035 Å, defined as plane II; N1, C13, C14, C15, O1 and O2 is nearly coplanar with the mean deviation of 0.0371 Å, defined as plane III. Plane III make a dihedral angle with plane I and plane II of 5.921 (74) and 50.207 (56) °, while the dihedral angle between plane I and plane II is 55.247 (72) °. The bond distance C13—C14 (1.360 (3) Å) falls in the range of a typical double bond, and C13—N1 bond (1.343 (3) Å) is shorter than the standard C—N single bond (1.48 Å), but longer than a C—N double bond (1.28 Å). This clearly indicates that the p orbital of N1 is conjugated with the π molecular orbital of C13—C14 double bond. All other double bonds and single bonds in the molecule fall in normal range of bond lengths.

The molecule is stabilized by intramolecular interactions N1—H1···O1 and N1—H1···F1 (Table 1), and form one-dimensional infinite chains via intermolecular hydrogen bonds C6—H6···O1 (Table 1). These chains are interconnected via weak C18—H18C···π (centroid of C7-C12 ring) interactions (Table 1 and Fig. 2).

Related literature top

For related literature, see: Xiao, Fang et al. (2008); Xiao, Li, Shi et al. (2008); Xiao, Li et al. (2008); Xiao, Lv et al. (2008); Xiao, Xue et al. (2007); Xiao, Fang et al. (2007). It would be much more useful to readers if the "Related literature" section had some kind of simple sub-division, so that, instead of just "For related literature, see···" it said, for example, "For general background, see···. For related structures, see···.? etc. Please revise this section as indicated. Cg1 is the centroid of C7–C12 ring.

Experimental top

Equimolar quantities (6 mmol) of ethyl 2-(4-methoxyphenyl)-3- oxopropanoate (1.33 g) and 2,4-difluorobenzenamine (0.77 g) in absolute alcohol (18 ml) were heated at 344–354 K for 1.5 h. The excess solvent was removed under reduced pressure. The residue was purified by a flash chromatography with EtOAc-petrolum ether to afford two fractions. The second fraction gave a E-isomer, and the first fraction, after partial solvent evaporated, furnished colorless blocks of (I) suitable for single-crystal structure determination.

Refinement top

The H atom bonded to N1 was located in a difference Fourier map and refined freely. All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H = 0.93, 0.96 and 0.97 Å for the aromatic, CH3 and CH2 type H atoms, respectively. Uiso = 1.2Ueq(parent atoms) were assigned for amino, aromatic and CH2 type H-atoms and 1.5Ueq(parent atoms) for CH3 type H-atoms.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Dashed lines indicate H-bonds.
[Figure 2] Fig. 2. The crystal packing of the title compound. Dashed lines indicate C—H···O and C—H···pi hydrogen bonds.
(Z)-Ethyl 3-(2,4-difluoroanilino)-2-(4-methoxyphenyl)acrylate top
Crystal data top
C18H17F2NO3F(000) = 696
Mr = 333.33Dx = 1.347 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1729 reflections
a = 17.295 (4) Åθ = 1.4–24.7°
b = 7.2940 (15) ŵ = 0.11 mm−1
c = 14.233 (3) ÅT = 298 K
β = 113.73 (3)°Block, colorless
V = 1643.7 (7) Å30.30 × 0.20 × 0.10 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer		2974 independent reflections
Radiation source: fine-focus sealed tube1889 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
ω/2θ scansθmax = 25.3°, θmin = 1.3°
Absorption correction: ψ scan
(North et al., 1968)		h = −20→19
Tmin = 0.969, Tmax = 0.989k = −8→0
3108 measured reflectionsl = 0→17
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)] = 0.053H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.156 w = 1/[σ2(Fo2) + (0.084P)2 + 0.0301P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.003
2974 reflectionsΔρmax = 0.20 e Å−3
224 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: 0.023 (3)
Crystal data top
C18H17F2NO3V = 1643.7 (7) Å3
Mr = 333.33Z = 4
Monoclinic, P21/cMo Kα radiation
a = 17.295 (4) ŵ = 0.11 mm−1
b = 7.2940 (15) ÅT = 298 K
c = 14.233 (3) Å0.30 × 0.20 × 0.10 mm
β = 113.73 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer		2974 independent reflections
Absorption correction: ψ scan
(North et al., 1968)		1889 reflections with I > 2σ(I)
Tmin = 0.969, Tmax = 0.989Rint = 0.016
3108 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.156H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.20 e Å−3
2974 reflectionsΔρmin = −0.19 e Å−3
224 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
C1−0.01149 (13)0.2255 (3)0.45020 (18)0.0442 (6)
C2−0.09169 (14)0.2175 (4)0.44819 (18)0.0482 (6)
C3−0.16098 (15)0.1544 (4)0.3666 (2)0.0577 (7)
H3−0.21430.15190.36800.069*
C4−0.14800 (15)0.0951 (4)0.28276 (19)0.0569 (7)
C5−0.07067 (16)0.0977 (4)0.27953 (19)0.0601 (7)
H5−0.06380.05620.22160.072*
C6−0.00210 (15)0.1628 (4)0.36312 (18)0.0536 (7)
H60.05100.16470.36110.064*
C70.28914 (13)0.3614 (3)0.64133 (17)0.0420 (6)
C80.35651 (13)0.2735 (3)0.71676 (17)0.0461 (6)
H80.34770.21420.76950.055*
C90.43614 (14)0.2706 (4)0.71668 (18)0.0492 (6)
H90.48010.21040.76860.059*
C100.45026 (14)0.3584 (3)0.63826 (18)0.0450 (6)
C110.38407 (14)0.4464 (4)0.56174 (19)0.0501 (7)
H110.39280.50420.50860.060*
C120.30493 (14)0.4487 (3)0.56390 (17)0.0472 (6)
H120.26120.51010.51240.057*
C130.13613 (13)0.3038 (3)0.55292 (18)0.0454 (6)
H130.14870.27450.49700.055*
C140.20243 (14)0.3552 (3)0.64003 (17)0.0438 (6)
C150.18698 (15)0.4010 (3)0.73038 (19)0.0486 (6)
C160.24764 (19)0.4999 (5)0.9037 (2)0.0767 (9)
H16A0.22560.39250.92490.092*
H16B0.20880.60070.89480.092*
C170.3318 (2)0.5471 (5)0.9828 (2)0.0838 (10)
H17A0.37080.44990.98810.126*
H17B0.32800.56331.04770.126*
H17C0.35130.65870.96390.126*
C180.59583 (14)0.2750 (4)0.7079 (2)0.0709 (9)
H18A0.60260.31840.77450.106*
H18B0.64640.29950.69750.106*
H18C0.58540.14530.70360.106*
F1−0.10159 (8)0.2760 (2)0.53363 (11)0.0670 (5)
F2−0.21570 (10)0.0299 (3)0.20048 (12)0.0843 (6)
H10.0432 (15)0.311 (4)0.5919 (19)0.059 (8)*
N10.05458 (11)0.2904 (3)0.53817 (16)0.0500 (6)
O10.11846 (11)0.3870 (3)0.73643 (13)0.0660 (6)
O20.25571 (10)0.4636 (3)0.80903 (12)0.0558 (5)
O30.52661 (9)0.3660 (3)0.63138 (13)0.0598 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0416 (12)0.0463 (15)0.0459 (14)0.0017 (11)0.0188 (11)0.0039 (12)
C20.0461 (14)0.0581 (16)0.0457 (14)0.0045 (12)0.0240 (12)0.0035 (12)
C30.0407 (13)0.0704 (19)0.0578 (17)−0.0009 (13)0.0153 (12)0.0069 (15)
C40.0483 (15)0.0653 (18)0.0465 (15)−0.0029 (13)0.0080 (12)0.0009 (13)
C50.0618 (17)0.0738 (19)0.0476 (15)0.0055 (15)0.0249 (13)−0.0054 (14)
C60.0467 (14)0.0683 (18)0.0505 (15)−0.0002 (13)0.0244 (12)−0.0037 (14)
C70.0416 (13)0.0416 (14)0.0442 (13)−0.0025 (11)0.0185 (11)−0.0061 (11)
C80.0469 (13)0.0485 (15)0.0463 (14)0.0036 (12)0.0223 (11)0.0040 (12)
C90.0444 (13)0.0539 (16)0.0461 (14)0.0096 (12)0.0148 (11)0.0048 (12)
C100.0402 (12)0.0484 (15)0.0486 (14)0.0006 (11)0.0203 (11)−0.0049 (12)
C110.0473 (14)0.0597 (17)0.0478 (14)0.0012 (12)0.0236 (12)0.0077 (13)
C120.0416 (13)0.0531 (16)0.0449 (14)0.0037 (12)0.0155 (11)0.0054 (12)
C130.0429 (13)0.0489 (15)0.0497 (14)0.0010 (11)0.0240 (11)−0.0006 (12)
C140.0438 (13)0.0450 (15)0.0469 (14)−0.0007 (11)0.0228 (11)0.0010 (12)
C150.0491 (14)0.0476 (15)0.0536 (15)−0.0027 (12)0.0253 (13)0.0020 (12)
C160.087 (2)0.107 (3)0.0471 (16)−0.0039 (19)0.0380 (16)−0.0040 (17)
C170.107 (3)0.089 (3)0.0507 (17)−0.012 (2)0.0272 (18)−0.0072 (17)
C180.0430 (14)0.087 (2)0.078 (2)0.0110 (15)0.0204 (14)0.0032 (18)
F10.0506 (8)0.1011 (13)0.0573 (9)0.0033 (8)0.0300 (7)−0.0085 (9)
F20.0611 (10)0.1115 (15)0.0617 (10)−0.0110 (10)0.0054 (8)−0.0135 (10)
N10.0404 (11)0.0651 (15)0.0487 (13)−0.0016 (10)0.0222 (10)−0.0053 (11)
O10.0548 (11)0.0921 (15)0.0633 (12)−0.0091 (10)0.0366 (9)−0.0091 (11)
O20.0578 (11)0.0708 (13)0.0449 (10)−0.0087 (9)0.0271 (8)−0.0088 (9)
O30.0412 (9)0.0763 (13)0.0671 (12)0.0043 (9)0.0274 (9)0.0062 (10)
Geometric parameters (Å, º) top
C1—C21.377 (3)C11—C121.382 (3)
C1—C61.390 (3)C11—H110.9300
C1—N11.395 (3)C12—H120.9300
C2—F11.363 (3)C13—N11.343 (3)
C2—C31.370 (3)C13—C141.360 (3)
C3—C41.369 (4)C13—H130.9300
C3—H30.9300C14—C151.454 (3)
C4—C51.357 (3)C15—O11.226 (3)
C4—F21.365 (3)C15—O21.343 (3)
C5—C61.383 (3)C16—O21.435 (3)
C5—H50.9300C16—C171.479 (4)
C6—H60.9300C16—H16A0.9700
C7—C81.384 (3)C16—H16B0.9700
C7—C121.392 (3)C17—H17A0.9600
C7—C141.493 (3)C17—H17B0.9600
C8—C91.378 (3)C17—H17C0.9600
C8—H80.9300C18—O31.418 (3)
C9—C101.391 (3)C18—H18A0.9600
C9—H90.9300C18—H18B0.9600
C10—O31.364 (3)C18—H18C0.9600
C10—C111.380 (3)N1—H10.88 (2)
C2—C1—C6116.5 (2)C11—C12—H12119.2
C2—C1—N1119.2 (2)C7—C12—H12119.2
C6—C1—N1124.4 (2)N1—C13—C14127.6 (2)
F1—C2—C3118.7 (2)N1—C13—H13116.2
F1—C2—C1117.1 (2)C14—C13—H13116.2
C3—C2—C1124.2 (2)C13—C14—C15118.8 (2)
C4—C3—C2116.8 (2)C13—C14—C7119.6 (2)
C4—C3—H3121.6C15—C14—C7121.6 (2)
C2—C3—H3121.6O1—C15—O2121.7 (2)
C5—C4—F2119.5 (2)O1—C15—C14124.7 (2)
C5—C4—C3122.3 (2)O2—C15—C14113.5 (2)
F2—C4—C3118.2 (2)O2—C16—C17108.6 (2)
C4—C5—C6119.4 (2)O2—C16—H16A110.0
C4—C5—H5120.3C17—C16—H16A110.0
C6—C5—H5120.3O2—C16—H16B110.0
C5—C6—C1120.8 (2)C17—C16—H16B110.0
C5—C6—H6119.6H16A—C16—H16B108.3
C1—C6—H6119.6C16—C17—H17A109.5
C8—C7—C12117.0 (2)C16—C17—H17B109.5
C8—C7—C14121.6 (2)H17A—C17—H17B109.5
C12—C7—C14121.3 (2)C16—C17—H17C109.5
C9—C8—C7122.4 (2)H17A—C17—H17C109.5
C9—C8—H8118.8H17B—C17—H17C109.5
C7—C8—H8118.8O3—C18—H18A109.5
C8—C9—C10119.5 (2)O3—C18—H18B109.5
C8—C9—H9120.3H18A—C18—H18B109.5
C10—C9—H9120.3O3—C18—H18C109.5
O3—C10—C11116.4 (2)H18A—C18—H18C109.5
O3—C10—C9124.3 (2)H18B—C18—H18C109.5
C11—C10—C9119.3 (2)C13—N1—C1126.5 (2)
C10—C11—C12120.2 (2)C13—N1—H1116.2 (16)
C10—C11—H11119.9C1—N1—H1116.8 (16)
C12—C11—H11119.9C15—O2—C16117.2 (2)
C11—C12—C7121.6 (2)C10—O3—C18117.9 (2)
C6—C1—C2—F1179.1 (2)C8—C7—C12—C110.6 (3)
N1—C1—C2—F10.5 (4)C14—C7—C12—C11−176.4 (2)
C6—C1—C2—C3−0.7 (4)N1—C13—C14—C150.6 (4)
N1—C1—C2—C3−179.2 (2)N1—C13—C14—C7179.9 (2)
F1—C2—C3—C4−179.3 (2)C8—C7—C14—C13−128.3 (3)
C1—C2—C3—C40.4 (4)C12—C7—C14—C1348.6 (3)
C2—C3—C4—C50.0 (4)C8—C7—C14—C1551.0 (3)
C2—C3—C4—F2179.5 (2)C12—C7—C14—C15−132.1 (2)
F2—C4—C5—C6−179.7 (2)C13—C14—C15—O14.3 (4)
C3—C4—C5—C6−0.2 (5)C7—C14—C15—O1−174.9 (2)
C4—C5—C6—C10.0 (4)C13—C14—C15—O2−175.0 (2)
C2—C1—C6—C50.4 (4)C7—C14—C15—O25.7 (3)
N1—C1—C6—C5178.9 (2)C14—C13—N1—C1−175.4 (2)
C12—C7—C8—C9−0.1 (4)C2—C1—N1—C13178.8 (2)
C14—C7—C8—C9177.0 (2)C6—C1—N1—C130.4 (4)
C7—C8—C9—C10−0.1 (4)O1—C15—O2—C164.9 (4)
C8—C9—C10—O3179.2 (2)C14—C15—O2—C16−175.7 (2)
C8—C9—C10—C11−0.2 (4)C17—C16—O2—C15173.7 (2)
O3—C10—C11—C12−178.7 (2)C11—C10—O3—C18−179.2 (2)
C9—C10—C11—C120.7 (4)C9—C10—O3—C181.5 (4)
C10—C11—C12—C7−1.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O1i0.932.513.280 (3)140
C18—H18C···Cg1ii0.962.923.631132
N1—H1···F10.88 (2)2.31 (2)2.678 (2)105.0 (18)
N1—H1···O10.88 (2)2.02 (2)2.678 (3)131 (2)
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, −y−1, −z+1.

Experimental details

Crystal data
Chemical formulaC18H17F2NO3
Mr333.33
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)17.295 (4), 7.2940 (15), 14.233 (3)
β (°) 113.73 (3)
V (Å3)1643.7 (7)
Z4
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.969, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections		3108, 2974, 1889
Rint0.016
(sin θ/λ)max (Å−1)0.600
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.156, 1.02
No. of reflections2974
No. of parameters224
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.20, −0.19

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O1i0.932.513.280 (3)139.8
C18—H18C···Cg1ii0.962.923.631132.0
N1—H1···F10.88 (2)2.31 (2)2.678 (2)105.0 (18)
N1—H1···O10.88 (2)2.02 (2)2.678 (3)131 (2)
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, −y−1, −z+1.
 

Acknowledgements

The work was financed by a grant (No. JSDXKYZZ0801) from Jishou University for talent introduction, China.

References

First citationEnraf–Nonius. (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
 First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.  Google Scholar
 First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationXiao, Z.-P., Fang, R.-Q., Li, H.-Q., Shi, L., Xue, J.-Y., Zheng, Y. & Zhu, H.-L. (2008). Eur. J. Med. Chem. 43, 1828–1836.  Web of Science CSD CrossRef PubMed CAS Google Scholar
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 First citationXiao, Z.-P., Li, H.-Q., Xue, J.-Y., Shi, L. & Zhu, H.-L. (2008). Synth. Commun. 38, 525–529.  Web of Science CrossRef CAS Google Scholar
 First citationXiao, Z.-P., Lv, P.-C., Xu, S.-P., Zhu, T.-T. & Zhu, H.-L. (2008). ChemMedChem, 3, 1516–1519.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationXiao, Z.-P., Xue, J.-Y., Tan, S.-H., Li, H.-Q. & Zhu, H.-L. (2007). Bioorg. Med. Chem. 15, 4212–4219.  Web of Science CSD CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 64| Part 12| December 2008| Page o2371
doi:10.1107/S1600536808036982
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