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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 66| Part 5| May 2010| Page o1083
https://doi.org/10.1107/S1600536810013127

Ethyl 6-[4-(di­methyl­amino)phen­yl]-4-hydr­­oxy-2-oxo-4-(tri­fluoro­methyl)­hexa­hydro­pyrimidine-5-carboxyl­ate

Xiao-Ping Song,a Gong-Chun Li,a Chang-Zeng Wua and Feng-Ling Yanga*

aCollege of Chemistry and Chemical Engineering, Xuchang University, Henan Province 461000, People's Republic of China
*Correspondence e-mail: actaeli@gmail.com

(Received 2 April 2010; accepted 9 April 2010; online 14 April 2010)

The title compound, C16H20F3N3O4, was prepared by reaction of 4-(dimethyl­amino)benzaldehyde, ethyl 4,4,4-trifluoro-3-oxo­butanoate and urea. In the title mol­ecule, the pyrimidine ring adopts a half-chair conformation and there is an intra­molecular hydrogen bond (O—H⋯O). The crystal structure is stabilized by two types inter­molecular hydrogen bonds (N—H⋯O and N—H⋯N).

Related literature

For the bioactivity of dihydro­pyrimidines, see: Brier et al. (2004[Brier, S., Lemaire, D., DeBonis, S., Forest, E. & Kozielski, F. (2004). Biochemistry, 43, 13072-13082.]); Cochran et al. (2005[Cochran, J. C., Gatial, J. E., Kapoor, T. M. & Gilbert, S. P. (2005). J. Biol. Chem. 280, 12658-12667.]); Moran et al. (2007[Moran, M. M., Fanger, C., Chong, J. A., McNamara, C., Zhen, X. G. & &Mandel-Brehm, J. (2007). WO Patent No. 2007073505.]); Zorkun et al. (2006[Zorkun, I. S., Sarac, S., Celebi, S. & Erol, K. (2006). Bioorg. Med. Chem. 14, 8582-8589.]). For the bioactivity of organofluorine compounds, see: Hermann et al. (2003[Hermann, B., Erwin, H. & Hansjorg, K. (2003). US Patent No. 2003176284.]); Ulrich (2004[Ulrich, H. (2004). US Patent No. 2004033897.]).

[Scheme 1]

Experimental

Crystal data

  • C16H20F3N3O4

  • Mr = 375.35

  • Monoclinic, P 21 /n

  • a = 13.319 (4) Å

  • b = 7.923 (2) Å

  • c = 16.530 (5) Å

  • β = 92.720 (5)°

  • V = 1742.3 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.12 mm−1

  • T = 116 K

  • 0.24 × 0.20 × 0.14 mm
Data collection

  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]) Tmin = 0.971, Tmax = 0.983

  • 11487 measured reflections

  • 3081 independent reflections

  • 2522 reflections with I > 2σ(I)

  • Rint = 0.030
Refinement

  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.107

  • S = 1.07

  • 3081 reflections

  • 250 parameters

  • 3 restraints

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

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯O3 0.86 (1) 1.97 (1) 2.7601 (16) 153 (2)
N1—H1A⋯O2i 0.90 (1) 1.91 (1) 2.8049 (15) 174 (2)
N2—H2A⋯N3ii 0.90 (1) 2.12 (1) 3.0241 (18) 178 (2)
Symmetry codes: (i) -x+2, -y+2, -z+2; (ii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810013127/om2331sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810013127/om2331Isup2.hkl

checkCIF report


Comment top

Dihydropyrimidine (DHPM) derivatives can be used as potential calcium channel blockers (Zorkun et al., 2006), inhibitors of mitotic kinesin Eg5 for treating cancer (Cochran et al., 2005; Brier et al., 2004) and as TRPA1 modulators for treating pain (Moran et al., 2007). Besides, compounds that contain fluorine have special bioactivity, for example, flumioxazin is a widely used herbicide (Hermann et al., 2003; Ulrich, 2004). This led us to pay much attention to the synthesis and bioactivity of these important fused perfluoroalkylated heterocyclic compounds. During the synthesis of DHPM derivatives, the title compound, an intermediate, was isolated and confirmed by X-ray diffraction to elucidate the reaction mechanism. We report here the crystal structure of the title compound(Fig. 1).

In the title molecule, the pyrimidine ring adopts a half-chair conformation, and there is an intramolecular hydrogen bond (O—H···O). The crystal structure is stabilized by two types intermolecular hydrogen bonds (N—H···O, and N—H···N).

Related literature top

For the bioactivity of dihydropyrimidines, see: Brier et al. (2004); Cochran et al. (2005); Moran et al. (2007); Zorkun et al. (2006). For the bioactivity of organofluorine compounds, see: Hermann et al. (2003); Ulrich (2004).

Experimental top

The title compound was synthesized by 4-(dimethylamino)-benzaldehyde (2.98 g, 20 mmol), ethyl 4,4,4-trifluoro-3-oxobutanoate(4.42 g, 24 mmol), and urea (1.80 g, 30 mmol), catalyzed by sulfamic acid(0.6 g), in the solvent of ethanol(20 ml), by refluxing for 3 h under the conditions of stirring. The solvent was evaporated in vacuo and the residue was washed with water. The title compound was recrystallized from ethanol and single crystals of (I) were obtained by slow evaporation.

Refinement top

H atoms of N and O were positioned freely refined. The other H atoms were placed in calculated positions, with C—H = 0.93, 0.96, 0.97 or 0.98 Å, and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2Ueq(C).

Structure description top

Dihydropyrimidine (DHPM) derivatives can be used as potential calcium channel blockers (Zorkun et al., 2006), inhibitors of mitotic kinesin Eg5 for treating cancer (Cochran et al., 2005; Brier et al., 2004) and as TRPA1 modulators for treating pain (Moran et al., 2007). Besides, compounds that contain fluorine have special bioactivity, for example, flumioxazin is a widely used herbicide (Hermann et al., 2003; Ulrich, 2004). This led us to pay much attention to the synthesis and bioactivity of these important fused perfluoroalkylated heterocyclic compounds. During the synthesis of DHPM derivatives, the title compound, an intermediate, was isolated and confirmed by X-ray diffraction to elucidate the reaction mechanism. We report here the crystal structure of the title compound(Fig. 1).

In the title molecule, the pyrimidine ring adopts a half-chair conformation, and there is an intramolecular hydrogen bond (O—H···O). The crystal structure is stabilized by two types intermolecular hydrogen bonds (N—H···O, and N—H···N).

For the bioactivity of dihydropyrimidines, see: Brier et al. (2004); Cochran et al. (2005); Moran et al. (2007); Zorkun et al. (2006). For the bioactivity of organofluorine compounds, see: Hermann et al. (2003); Ulrich (2004).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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: CrystalStructure (Rigaku/MSC, 2005).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, (I), with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. The packing diagram of the title compound. Intermolecular hydrogen bonds are shown as dashed line.
Ethyl 6-[4-(dimethylamino)phenyl]-4-hydroxy-2-oxo-4-(trifluoromethyl)hexahydropyrimidine-5-carboxylate top
Crystal data top
C16H20F3N3O4F(000) = 784
Mr = 375.35Dx = 1.431 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 13.319 (4) ÅCell parameters from 6970 reflections
b = 7.923 (2) Åθ = 1.5–27.9°
c = 16.530 (5) ŵ = 0.12 mm−1
β = 92.720 (5)°T = 116 K
V = 1742.3 (9) Å3Prism, colorless
Z = 40.24 × 0.20 × 0.14 mm
Data collection top
Rigaku Saturn CCD area-detector
diffractometer		3081 independent reflections
Radiation source: rotating anode2522 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.030
Detector resolution: 14.63 pixels mm-1θmax = 25.0°, θmin = 1.9°
ω and φ scansh = −15→15
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)		k = −9→9
Tmin = 0.971, Tmax = 0.983l = −19→18
11487 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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0725P)2]
where P = (Fo2 + 2Fc2)/3
3081 reflections(Δ/σ)max = 0.001
250 parametersΔρmax = 0.17 e Å−3
3 restraintsΔρmin = −0.24 e Å−3
Crystal data top
C16H20F3N3O4V = 1742.3 (9) Å3
Mr = 375.35Z = 4
Monoclinic, P21/nMo Kα radiation
a = 13.319 (4) ŵ = 0.12 mm−1
b = 7.923 (2) ÅT = 116 K
c = 16.530 (5) Å0.24 × 0.20 × 0.14 mm
β = 92.720 (5)°
Data collection top
Rigaku Saturn CCD area-detector
diffractometer		3081 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)		2522 reflections with I > 2σ(I)
Tmin = 0.971, Tmax = 0.983Rint = 0.030
11487 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0373 restraints
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.17 e Å−3
3081 reflectionsΔρmin = −0.24 e Å−3
250 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 > 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
F20.76872 (7)0.70609 (12)1.19210 (5)0.0422 (3)
F30.87687 (7)0.90599 (12)1.18384 (5)0.0419 (3)
F10.73912 (7)0.91322 (12)1.11033 (6)0.0434 (3)
O10.93596 (8)0.60732 (13)1.11199 (6)0.0292 (3)
O20.96896 (7)0.91625 (12)0.90354 (6)0.0262 (3)
O30.78789 (9)0.36331 (13)1.10635 (6)0.0385 (3)
O40.63911 (8)0.47358 (14)1.06174 (7)0.0362 (3)
N10.90896 (9)0.83310 (15)1.02318 (7)0.0231 (3)
N20.87955 (8)0.67473 (14)0.90588 (7)0.0216 (3)
N30.57474 (8)0.09436 (13)0.76740 (7)0.0214 (3)
C10.81144 (11)0.81114 (19)1.14029 (9)0.0296 (4)
C20.86240 (10)0.71282 (17)1.07362 (8)0.0220 (3)
C30.78493 (10)0.60970 (16)1.02222 (8)0.0208 (3)
H30.73170.68501.00070.025*
C40.84102 (10)0.53309 (17)0.95139 (8)0.0198 (3)
H40.89800.46690.97360.024*
C50.92246 (10)0.81105 (16)0.94208 (8)0.0202 (3)
C60.73872 (11)0.46902 (19)1.06923 (9)0.0275 (3)
C70.58484 (14)0.3318 (2)1.09539 (11)0.0478 (5)
H7A0.52310.37171.11760.057*
H7B0.62560.27991.13880.057*
C80.56152 (16)0.2067 (2)1.03137 (11)0.0555 (6)
H8A0.52350.25970.98760.083*
H8B0.52290.11641.05300.083*
H8C0.62300.16251.01180.083*
C90.77484 (10)0.41978 (16)0.89851 (8)0.0190 (3)
C100.79225 (10)0.24776 (18)0.89719 (8)0.0213 (3)
H100.84790.20400.92620.026*
C110.72844 (10)0.13904 (17)0.85356 (8)0.0219 (3)
H110.74190.02390.85350.026*
C120.64423 (10)0.20114 (16)0.80974 (8)0.0195 (3)
C130.63014 (10)0.37648 (17)0.80716 (8)0.0225 (3)
H130.57720.42150.77540.027*
C140.69393 (10)0.48298 (17)0.85123 (8)0.0226 (3)
H140.68270.59880.84930.027*
C150.58978 (11)−0.08702 (17)0.77979 (8)0.0254 (3)
H15A0.6557−0.11790.76400.038*
H15B0.5403−0.14830.74760.038*
H15C0.5832−0.11370.83590.038*
C160.46919 (10)0.14840 (19)0.77106 (9)0.0301 (4)
H16A0.45640.18300.82530.045*
H16B0.42560.05610.75570.045*
H16C0.45680.24120.73460.045*
H10.9050 (13)0.5138 (16)1.1199 (12)0.054 (6)*
H1A0.9442 (11)0.9186 (15)1.0458 (9)0.032 (4)*
H2A0.8942 (11)0.6524 (19)0.8542 (6)0.032 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F20.0505 (6)0.0475 (6)0.0302 (5)−0.0197 (5)0.0198 (4)−0.0068 (4)
F30.0473 (6)0.0502 (6)0.0291 (5)−0.0227 (5)0.0115 (4)−0.0174 (4)
F10.0429 (6)0.0419 (6)0.0464 (6)0.0076 (4)0.0123 (5)−0.0114 (4)
O10.0280 (6)0.0337 (6)0.0254 (6)−0.0022 (5)−0.0052 (4)0.0032 (5)
O20.0299 (6)0.0269 (5)0.0219 (5)−0.0110 (4)0.0029 (4)0.0007 (4)
O30.0505 (8)0.0332 (6)0.0315 (6)−0.0106 (5)−0.0021 (5)0.0088 (5)
O40.0305 (7)0.0399 (7)0.0393 (6)−0.0165 (5)0.0135 (5)−0.0066 (5)
N10.0258 (7)0.0239 (6)0.0197 (6)−0.0091 (5)0.0022 (5)−0.0034 (5)
N20.0252 (7)0.0218 (6)0.0180 (6)−0.0073 (5)0.0039 (5)−0.0013 (5)
N30.0208 (6)0.0217 (6)0.0215 (6)−0.0029 (5)0.0001 (5)−0.0020 (5)
C10.0296 (9)0.0324 (8)0.0274 (8)−0.0096 (7)0.0076 (6)−0.0048 (7)
C20.0199 (7)0.0257 (8)0.0206 (7)−0.0034 (6)0.0013 (5)0.0006 (6)
C30.0198 (7)0.0216 (7)0.0209 (7)−0.0017 (5)0.0010 (5)0.0001 (6)
C40.0182 (7)0.0199 (7)0.0213 (7)−0.0013 (5)0.0014 (5)0.0012 (6)
C50.0176 (7)0.0215 (7)0.0216 (7)0.0001 (6)0.0002 (5)−0.0010 (6)
C60.0317 (9)0.0284 (8)0.0227 (7)−0.0091 (7)0.0055 (6)−0.0051 (7)
C70.0497 (11)0.0533 (11)0.0422 (10)−0.0325 (9)0.0220 (8)−0.0074 (9)
C80.0750 (15)0.0473 (11)0.0461 (11)−0.0330 (10)0.0243 (10)−0.0123 (9)
C90.0187 (7)0.0203 (7)0.0181 (7)−0.0021 (5)0.0029 (5)0.0003 (5)
C100.0188 (7)0.0236 (7)0.0214 (7)0.0022 (6)−0.0006 (5)0.0007 (6)
C110.0247 (8)0.0166 (7)0.0244 (7)0.0005 (6)0.0021 (6)−0.0005 (6)
C120.0188 (7)0.0242 (7)0.0159 (6)−0.0029 (5)0.0037 (5)−0.0014 (5)
C130.0194 (7)0.0250 (8)0.0227 (7)0.0014 (6)−0.0028 (6)0.0013 (6)
C140.0258 (8)0.0170 (7)0.0250 (7)0.0014 (6)0.0006 (6)0.0016 (6)
C150.0295 (8)0.0238 (8)0.0229 (7)−0.0064 (6)0.0005 (6)−0.0007 (6)
C160.0216 (8)0.0375 (9)0.0312 (8)−0.0033 (6)0.0012 (6)−0.0079 (7)
Geometric parameters (Å, º) top
F2—C11.3403 (17)C4—H40.9800
F3—C11.3353 (17)C7—C81.472 (2)
F1—C11.3348 (18)C7—H7A0.9700
O1—C21.4149 (17)C7—H7B0.9700
O1—H10.860 (9)C8—H8A0.9600
O2—C51.2335 (16)C8—H8B0.9600
O3—C61.2119 (19)C8—H8C0.9600
O4—C61.3271 (19)C9—C101.3828 (19)
O4—C71.4601 (18)C9—C141.3938 (19)
N1—C51.3722 (18)C10—C111.3878 (19)
N1—C21.4273 (17)C10—H100.9300
N1—H1A0.896 (9)C11—C121.3956 (19)
N2—C51.3486 (18)C11—H110.9300
N2—C41.4578 (17)C12—C131.4021 (19)
N2—H2A0.902 (9)C13—C141.3805 (19)
N3—C121.4145 (17)C13—H130.9300
N3—C151.4640 (17)C14—H140.9300
N3—C161.4735 (18)C15—H15A0.9600
C1—C21.534 (2)C15—H15B0.9600
C2—C31.5397 (19)C15—H15C0.9600
C3—C61.5067 (19)C16—H16A0.9600
C3—C41.5429 (18)C16—H16B0.9600
C3—H30.9800C16—H16C0.9600
C4—C91.5079 (19)
C2—O1—H1104.5 (13)O4—C7—H7A109.8
C6—O4—C7117.02 (14)C8—C7—H7A109.8
C5—N1—C2124.51 (12)O4—C7—H7B109.8
C5—N1—H1A114.4 (11)C8—C7—H7B109.8
C2—N1—H1A119.6 (10)H7A—C7—H7B108.2
C5—N2—C4122.66 (11)C7—C8—H8A109.5
C5—N2—H2A118.1 (10)C7—C8—H8B109.5
C4—N2—H2A115.7 (10)H8A—C8—H8B109.5
C12—N3—C15115.84 (11)C7—C8—H8C109.5
C12—N3—C16114.14 (11)H8A—C8—H8C109.5
C15—N3—C16113.82 (11)H8B—C8—H8C109.5
F1—C1—F3107.46 (12)C10—C9—C14118.10 (12)
F1—C1—F2107.01 (12)C10—C9—C4120.13 (12)
F3—C1—F2106.92 (12)C14—C9—C4121.75 (12)
F1—C1—C2112.17 (12)C9—C10—C11121.39 (12)
F3—C1—C2111.93 (12)C9—C10—H10119.3
F2—C1—C2111.06 (12)C11—C10—H10119.3
O1—C2—N1110.21 (11)C10—C11—C12120.54 (13)
O1—C2—C1107.38 (11)C10—C11—H11119.7
N1—C2—C1107.45 (12)C12—C11—H11119.7
O1—C2—C3111.44 (11)C11—C12—C13117.92 (12)
N1—C2—C3109.29 (11)C11—C12—N3122.47 (12)
C1—C2—C3110.99 (11)C13—C12—N3119.60 (12)
C6—C3—C2112.79 (11)C14—C13—C12120.75 (12)
C6—C3—C4108.95 (11)C14—C13—H13119.6
C2—C3—C4106.95 (11)C12—C13—H13119.6
C6—C3—H3109.4C13—C14—C9121.09 (12)
C2—C3—H3109.4C13—C14—H14119.5
C4—C3—H3109.4C9—C14—H14119.5
N2—C4—C9111.69 (11)N3—C15—H15A109.5
N2—C4—C3106.48 (11)N3—C15—H15B109.5
C9—C4—C3112.54 (11)H15A—C15—H15B109.5
N2—C4—H4108.7N3—C15—H15C109.5
C9—C4—H4108.7H15A—C15—H15C109.5
C3—C4—H4108.7H15B—C15—H15C109.5
O2—C5—N2121.65 (12)N3—C16—H16A109.5
O2—C5—N1120.72 (12)N3—C16—H16B109.5
N2—C5—N1117.58 (12)H16A—C16—H16B109.5
O3—C6—O4125.44 (14)N3—C16—H16C109.5
O3—C6—C3123.25 (14)H16A—C16—H16C109.5
O4—C6—C3111.27 (13)H16B—C16—H16C109.5
O4—C7—C8109.59 (14)
C5—N1—C2—O193.48 (15)C2—N1—C5—N27.3 (2)
C5—N1—C2—C1−149.82 (13)C7—O4—C6—O3−5.4 (2)
C5—N1—C2—C3−29.31 (18)C7—O4—C6—C3172.21 (12)
F1—C1—C2—O1−179.00 (11)C2—C3—C6—O3−53.65 (18)
F3—C1—C2—O160.12 (15)C4—C3—C6—O364.94 (17)
F2—C1—C2—O1−59.30 (14)C2—C3—C6—O4128.71 (12)
F1—C1—C2—N162.46 (15)C4—C3—C6—O4−112.70 (13)
F3—C1—C2—N1−58.43 (15)C6—O4—C7—C8−94.93 (19)
F2—C1—C2—N1−177.85 (11)N2—C4—C9—C10128.63 (13)
F1—C1—C2—C3−56.98 (16)C3—C4—C9—C10−111.65 (14)
F3—C1—C2—C3−177.86 (11)N2—C4—C9—C14−52.72 (16)
F2—C1—C2—C362.72 (15)C3—C4—C9—C1467.00 (15)
O1—C2—C3—C652.81 (15)C14—C9—C10—C11−3.27 (19)
N1—C2—C3—C6174.86 (11)C4—C9—C10—C11175.43 (12)
C1—C2—C3—C6−66.81 (15)C9—C10—C11—C12−0.2 (2)
O1—C2—C3—C4−66.94 (13)C10—C11—C12—C134.00 (19)
N1—C2—C3—C455.11 (14)C10—C11—C12—N3−177.11 (11)
C1—C2—C3—C4173.44 (11)C15—N3—C12—C116.82 (18)
C5—N2—C4—C9165.79 (12)C16—N3—C12—C11141.96 (13)
C5—N2—C4—C342.56 (16)C15—N3—C12—C13−174.31 (12)
C6—C3—C4—N2177.15 (11)C16—N3—C12—C13−39.17 (16)
C2—C3—C4—N2−60.65 (13)C11—C12—C13—C14−4.37 (19)
C6—C3—C4—C954.46 (15)N3—C12—C13—C14176.70 (12)
C2—C3—C4—C9176.66 (11)C12—C13—C14—C91.0 (2)
C4—N2—C5—O2168.05 (12)C10—C9—C14—C132.89 (19)
C4—N2—C5—N1−14.73 (19)C4—C9—C14—C13−175.79 (12)
C2—N1—C5—O2−175.47 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O30.86 (1)1.97 (1)2.7601 (16)153 (2)
N1—H1A···O2i0.90 (1)1.91 (1)2.8049 (15)174 (2)
N2—H2A···N3ii0.90 (1)2.12 (1)3.0241 (18)178 (2)
Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) −x+3/2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formulaC16H20F3N3O4
Mr375.35
Crystal system, space groupMonoclinic, P21/n
Temperature (K)116
a, b, c (Å)13.319 (4), 7.923 (2), 16.530 (5)
β (°) 92.720 (5)
V (Å3)1742.3 (9)
Z4
Radiation typeMo Kα
µ (mm−1)0.12
Crystal size (mm)0.24 × 0.20 × 0.14
Data collection
DiffractometerRigaku Saturn CCD area-detector
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.971, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections		11487, 3081, 2522
Rint0.030
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.107, 1.07
No. of reflections3081
No. of parameters250
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.17, −0.24

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2005).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O30.860 (9)1.968 (12)2.7601 (16)152.5 (18)
N1—H1A···O2i0.896 (9)1.913 (9)2.8049 (15)173.8 (15)
N2—H2A···N3ii0.902 (9)2.122 (9)3.0241 (18)178.3 (15)
Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) −x+3/2, y+1/2, −z+3/2.
 

Acknowledgements

This work was supported by the Natural Science Foundation of Henan Province, China (grant No. 082300420110), and the Natural Science Foundation of Henan Province Education Department, China (grant No. 2007150036).

References

First citationBrier, S., Lemaire, D., DeBonis, S., Forest, E. & Kozielski, F. (2004). Biochemistry, 43, 13072–13082.  Web of Science CrossRef PubMed CAS Google Scholar
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 First citationRigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationUlrich, H. (2004). US Patent No. 2004033897.  Google Scholar
 First citationZorkun, I. S., Sarac, S., Celebi, S. & Erol, K. (2006). Bioorg. Med. Chem. 14, 8582–8589.  Web of Science 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 66| Part 5| May 2010| Page o1083
https://doi.org/10.1107/S1600536810013127
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