rac-Ethyl 4-hy­droxy-6-(2-hy­droxy­phen­yl)-2-oxo-4-(trifluoro­methyl)per­hydro­pyrimidine-5-carboxyl­ate

Song, X.-P.; Li, G.-C.; Zhu, F.-X.; Wu, C.-Z.

doi:10.1107/S1600536810021355

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1651

doi:10.1107/S1600536810021355

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rac-Ethyl 4-hydroxy-6-(2-hydroxyphenyl)-2-oxo-4-(trifluoromethyl)perhydropyrimidine-5-carboxylate

Xiao-Ping Song,^a Gong-Chun Li,^a Feng-Xiang Zhu ^a and Chang-Zeng Wu ^a ^*

^aCollege of Chemistry and Chemical Engineering, Xuchang University, Xuchang, Henan Province 461000, People's Republic of China
^*Correspondence e-mail: wchz3058@126.com

(Received 24 May 2010; accepted 4 June 2010; online 16 June 2010)

In the title compound, C₁₄H₁₅F₃N₂O₅, prepared by reaction of 2-hydroxybenzaldehyde, ethyl 4,4,4-trifluoro-3-oxobutanoate and urea, the tetrapyrimidine ring adopts a half-chair conformation. The crystal structure is stabilized by five intermolecular hydrogen bonds, three O—H⋯O and two N—H⋯O, giving cyclic dimers (through three hydrogen bonds) which are further extended into a two-dimensional network.

Related literature

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

Crystal data

C₁₄H₁₅F₃N₂O₅
M_r = 348.28
Monoclinic, P 2₁ /n
a = 12.0940 (15) Å
b = 8.665 (1) Å
c = 14.3110 (18) Å
β = 93.987 (6)°
V = 1496.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 113 K
0.26 × 0.22 × 0.20 mm

Data collection

Rigaku Saturn724 CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2009 ) T_min = 0.965, T_max = 0.973
15222 measured reflections
3558 independent reflections
2461 reflections with I > 2σ(I)'
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.075
S = 0.96
3558 reflections
234 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H4⋯O1ⁱ	0.836 (14)	2.244 (14)	3.0760 (13)	174.1 (14)
N2—H5⋯O2ⁱⁱ	0.867 (14)	2.040 (15)	2.9064 (14)	177.4 (13)
O1—H1⋯O5ⁱ	0.858 (17)	2.588 (16)	3.0983 (13)	119.2 (13)
O1—H1⋯O3ⁱ	0.858 (17)	2.013 (17)	2.8232 (13)	157.1 (15)
O5—H6⋯O2ⁱⁱⁱ	0.912 (16)	1.759 (17)	2.6685 (12)	175.8 (14)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y, -z+2; (iii) x, y+1, z.

Data collection: CrystalClear-SM Expert (Rigaku, 2009); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2009); software used to prepare material for publication: CrystalStructure.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810021355/zs2042sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810021355/zs2042Isup2.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). In addition, compounds that contain fluorine have special bioactivity, e.g. flumioxazin is a widely used herbicide (Hermann et al., 2003; Ulrich, 2004). This led us to focus our attention on the synthesis and bioactivity of these important fused perfluoroalkylated heterocyclic compounds. During the synthesis of DHPM derivatives, the title compound, an intermediate C₁₄H₁₅F₃N₂O₅ (I) was isolated and the structure confirmed by X-ray diffraction, in order to elucidate the reaction mechanism.

In the structure of the title molecule, the dihydropyrimidine ring adopts a half-chair conformation. The crystal structure is stabilized by five intermolecular hydrogen bonds, three O—H···O and two N—H···O (Table 1), giving cyclic dimers which are further extended into a two-dimensional network (Fig. 2).

dimension?

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 refluxing for 3 h, a stirred solution of 2-hydroxybenzaldehyde (0.61 g, 5 mmol), ethyl 4,4,4-trifluoro-3-oxobutanoate (1.11 g, 6 mmol) and urea (0.45 g, 7.5 mmol) in 5 ml of ethanol, the reaction catalyzed by sulfamic acid (0.15 g). The solvent was evaporated in vacuo and the residue was washed with water. The title compound was recrystallized from 50% aqueous ethanol and single crystals of (I) were obtained by slow evaporation.

Computing details top

Data collection: CrystalClear-SM Expert (Rigaku, 2009); cell refinement: CrystalClear-SM Expert (Rigaku, 2009); data reduction: CrystalClear-SM Expert (Rigaku, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2009); software used to prepare material for publication: CrystalStructure (Rigaku, 2009).

Figures top

	Fig. 1. Molecular configuration and atom numbering scheme for (I), with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The packing diagram of the title compound. Intermolecular hydrogen bonds are shown as dashed line.

rac-Ethyl 4-hydroxy-6-(2-hydroxyphenyl)-2-oxo-4-(trifluoromethyl)perhydropyrimidine- 5-carboxylate top

Crystal data top

C₁₄H₁₅F₃N₂O₅	F(000) = 720
M_r = 348.28	D_x = 1.546 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yn	Cell parameters from 4600 reflections
a = 12.0940 (15) Å	θ = 1.7–28.0°
b = 8.665 (1) Å	µ = 0.14 mm⁻¹
c = 14.3110 (18) Å	T = 113 K
β = 93.987 (6)°	Prism, colorless
V = 1496.1 (3) Å³	0.26 × 0.22 × 0.20 mm
Z = 4

Data collection top

Rigaku Saturn724 CCD diffractometer	3558 independent reflections
Radiation source: rotating anode	2461 reflections with I > 2σ(I)'
Multilayer monochromator	R_int = 0.043
Detector resolution: 14.222 pixels mm^-1	θ_max = 27.9°, θ_min = 2.1°
ω scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2009)	k = −10→11
T_min = 0.965, T_max = 0.973	l = −18→15
15222 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ²(F_o²) + (0.0366P)²] where P = (F_o² + 2F_c²)/3
3558 reflections	(Δ/σ)_max < 0.001
234 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₄H₁₅F₃N₂O₅	V = 1496.1 (3) Å³
M_r = 348.28	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.0940 (15) Å	µ = 0.14 mm⁻¹
b = 8.665 (1) Å	T = 113 K
c = 14.3110 (18) Å	0.26 × 0.22 × 0.20 mm
β = 93.987 (6)°

Data collection top

Rigaku Saturn724 CCD diffractometer	3558 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2009)	2461 reflections with I > 2σ(I)'
T_min = 0.965, T_max = 0.973	R_int = 0.043
15222 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Δρ_max = 0.29 e Å⁻³
3558 reflections	Δρ_min = −0.17 e Å⁻³
234 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

	x	y	z	U_iso*/U_eq
F1	0.63046 (7)	0.13597 (8)	0.56068 (5)	0.0284 (2)
F2	0.70104 (6)	−0.07799 (8)	0.61474 (5)	0.02243 (19)
F3	0.52483 (6)	−0.04190 (9)	0.61064 (5)	0.0278 (2)
O1	0.73825 (7)	0.17971 (10)	0.73408 (6)	0.0166 (2)
O2	0.57743 (7)	−0.12700 (9)	0.92883 (6)	0.0155 (2)
O3	0.61021 (7)	0.46053 (9)	0.68641 (6)	0.0188 (2)
O4	0.44283 (7)	0.37553 (9)	0.63011 (6)	0.0189 (2)
O5	0.57096 (8)	0.57378 (10)	0.88466 (7)	0.0226 (2)
N1	0.62882 (9)	−0.02277 (12)	0.79262 (7)	0.0144 (2)
N2	0.52802 (9)	0.11947 (11)	0.89483 (8)	0.0151 (2)
C1	0.63604 (10)	0.10070 (14)	0.72522 (9)	0.0136 (3)
C2	0.54011 (10)	0.21315 (13)	0.73746 (8)	0.0128 (3)
H2	0.4693	0.1572	0.7201	0.015*
C3	0.53875 (10)	0.26147 (13)	0.84121 (8)	0.0139 (3)
H3	0.6103	0.3134	0.8614	0.017*
C4	0.57828 (10)	−0.01283 (14)	0.87496 (9)	0.0137 (3)
C5	0.62326 (10)	0.02811 (14)	0.62678 (9)	0.0169 (3)
C6	0.53918 (10)	0.36240 (14)	0.68090 (8)	0.0144 (3)
C7	0.41216 (11)	0.52976 (14)	0.59613 (10)	0.0219 (3)
H7A	0.4704	0.5723	0.5582	0.026*
H7B	0.4024	0.6003	0.6494	0.026*
C8	0.30531 (11)	0.51220 (17)	0.53746 (10)	0.0273 (3)
H8A	0.3166	0.4433	0.4847	0.033*
H8B	0.2806	0.6135	0.5137	0.033*
H8C	0.2489	0.4683	0.5757	0.033*
C9	0.44302 (10)	0.37055 (13)	0.85540 (8)	0.0145 (3)
C10	0.46361 (10)	0.52609 (14)	0.87614 (8)	0.0157 (3)
C11	0.37451 (11)	0.62576 (15)	0.88661 (9)	0.0203 (3)
H11	0.3882	0.7312	0.9014	0.024*
C12	0.26690 (11)	0.57248 (15)	0.87573 (9)	0.0233 (3)
H12	0.2071	0.6412	0.8836	0.028*
C13	0.24560 (12)	0.41890 (15)	0.85339 (10)	0.0248 (3)
H13	0.1715	0.3824	0.8452	0.030*
C14	0.33378 (11)	0.31964 (15)	0.84326 (9)	0.0204 (3)
H14	0.3194	0.2146	0.8277	0.024*
H1	0.7889 (15)	0.1108 (18)	0.7422 (12)	0.046 (5)*
H4	0.6684 (12)	−0.1011 (15)	0.7884 (9)	0.021 (4)*
H5	0.4973 (12)	0.1248 (15)	0.9477 (11)	0.025 (4)*
H6	0.5734 (13)	0.6771 (19)	0.8967 (11)	0.043 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0430 (5)	0.0269 (4)	0.0157 (4)	0.0048 (4)	0.0052 (4)	0.0046 (3)
F2	0.0214 (4)	0.0232 (4)	0.0232 (4)	0.0060 (3)	0.0047 (3)	−0.0049 (3)
F3	0.0180 (4)	0.0365 (5)	0.0285 (5)	−0.0054 (4)	−0.0001 (3)	−0.0131 (4)
O1	0.0097 (4)	0.0138 (5)	0.0264 (5)	−0.0005 (4)	0.0010 (4)	0.0003 (4)
O2	0.0196 (5)	0.0110 (4)	0.0161 (5)	0.0002 (4)	0.0029 (4)	0.0015 (4)
O3	0.0161 (5)	0.0168 (5)	0.0234 (5)	−0.0030 (4)	−0.0004 (4)	0.0028 (4)
O4	0.0151 (5)	0.0168 (5)	0.0241 (5)	0.0006 (4)	−0.0041 (4)	0.0051 (4)
O5	0.0165 (5)	0.0134 (5)	0.0381 (6)	−0.0009 (4)	0.0021 (4)	−0.0064 (4)
N1	0.0154 (5)	0.0115 (5)	0.0168 (6)	0.0045 (4)	0.0049 (4)	0.0010 (4)
N2	0.0197 (6)	0.0118 (5)	0.0146 (6)	0.0027 (4)	0.0065 (4)	0.0009 (4)
C1	0.0105 (6)	0.0133 (6)	0.0172 (7)	−0.0007 (5)	0.0014 (5)	0.0020 (5)
C2	0.0114 (6)	0.0120 (6)	0.0150 (7)	0.0009 (5)	0.0013 (5)	0.0010 (5)
C3	0.0135 (6)	0.0131 (6)	0.0152 (7)	0.0001 (5)	0.0017 (5)	0.0014 (5)
C4	0.0113 (6)	0.0132 (6)	0.0163 (7)	−0.0022 (5)	−0.0009 (5)	−0.0015 (5)
C5	0.0148 (6)	0.0171 (6)	0.0189 (7)	0.0016 (5)	0.0027 (5)	0.0010 (5)
C6	0.0128 (6)	0.0166 (7)	0.0138 (7)	0.0021 (5)	0.0020 (5)	−0.0009 (5)
C7	0.0209 (7)	0.0161 (7)	0.0282 (8)	0.0041 (5)	−0.0009 (6)	0.0072 (6)
C8	0.0217 (7)	0.0306 (8)	0.0291 (8)	0.0048 (6)	−0.0013 (6)	0.0094 (6)
C9	0.0148 (6)	0.0139 (6)	0.0153 (7)	0.0023 (5)	0.0036 (5)	0.0024 (5)
C10	0.0149 (6)	0.0150 (6)	0.0172 (7)	0.0009 (5)	0.0015 (5)	0.0004 (5)
C11	0.0209 (7)	0.0143 (7)	0.0257 (8)	0.0033 (5)	0.0018 (6)	−0.0028 (6)
C12	0.0178 (7)	0.0223 (7)	0.0302 (8)	0.0081 (6)	0.0045 (6)	−0.0003 (6)
C13	0.0150 (7)	0.0246 (7)	0.0353 (8)	0.0003 (6)	0.0049 (6)	−0.0016 (6)
C14	0.0183 (7)	0.0147 (7)	0.0289 (8)	−0.0005 (5)	0.0059 (6)	−0.0017 (6)

Geometric parameters (Å, º) top

F1—C5	1.3370 (14)	C2—C3	1.5438 (17)
F2—C5	1.3350 (14)	C2—H2	1.0000
F3—C5	1.3418 (14)	C3—C9	1.5191 (16)
O1—C1	1.4110 (14)	C3—H3	1.0000
O1—H1	0.858 (17)	C7—C8	1.4990 (19)
O2—C4	1.2547 (14)	C7—H7A	0.9900
O3—C6	1.2073 (14)	C7—H7B	0.9900
O4—C6	1.3347 (15)	C8—H8A	0.9800
O4—C7	1.4611 (14)	C8—H8B	0.9800
O5—C10	1.3599 (15)	C8—H8C	0.9800
O5—H6	0.912 (16)	C9—C14	1.3922 (17)
N1—C4	1.3674 (15)	C9—C10	1.3986 (17)
N1—C1	1.4472 (16)	C10—C11	1.3971 (17)
N1—H4	0.836 (14)	C11—C12	1.3795 (18)
N2—C4	1.3373 (16)	C11—H11	0.9500
N2—C3	1.4606 (15)	C12—C13	1.3886 (19)
N2—H5	0.867 (14)	C12—H12	0.9500
C1—C2	1.5344 (16)	C13—C14	1.3856 (18)
C1—C5	1.5407 (18)	C13—H13	0.9500
C2—C6	1.5254 (16)	C14—H14	0.9500

C1—O1—H1	106.7 (11)	F3—C5—C1	111.93 (10)
C6—O4—C7	116.81 (10)	O3—C6—O4	124.46 (11)
C10—O5—H6	109.5 (10)	O3—C6—C2	125.69 (12)
C4—N1—C1	125.39 (10)	O4—C6—C2	109.59 (10)
C4—N1—H4	113.9 (9)	O4—C7—C8	106.41 (10)
C1—N1—H4	119.4 (9)	O4—C7—H7A	110.4
C4—N2—C3	123.51 (10)	C8—C7—H7A	110.4
C4—N2—H5	117.4 (9)	O4—C7—H7B	110.4
C3—N2—H5	118.2 (9)	C8—C7—H7B	110.4
O1—C1—N1	113.07 (10)	H7A—C7—H7B	108.6
O1—C1—C2	110.26 (10)	C7—C8—H8A	109.5
N1—C1—C2	108.19 (9)	C7—C8—H8B	109.5
O1—C1—C5	108.17 (9)	H8A—C8—H8B	109.5
N1—C1—C5	107.50 (10)	C7—C8—H8C	109.5
C2—C1—C5	109.58 (10)	H8A—C8—H8C	109.5
C6—C2—C1	117.10 (9)	H8B—C8—H8C	109.5
C6—C2—C3	106.28 (10)	C14—C9—C10	119.03 (11)
C1—C2—C3	109.92 (10)	C14—C9—C3	120.77 (11)
C6—C2—H2	107.7	C10—C9—C3	120.12 (11)
C1—C2—H2	107.7	O5—C10—C11	122.76 (11)
C3—C2—H2	107.7	O5—C10—C9	117.82 (10)
N2—C3—C9	110.95 (9)	C11—C10—C9	119.42 (11)
N2—C3—C2	106.50 (10)	C12—C11—C10	120.64 (12)
C9—C3—C2	110.89 (10)	C12—C11—H11	119.7
N2—C3—H3	109.5	C10—C11—H11	119.7
C9—C3—H3	109.5	C11—C12—C13	120.35 (12)
C2—C3—H3	109.5	C11—C12—H12	119.8
O2—C4—N2	121.47 (11)	C13—C12—H12	119.8
O2—C4—N1	120.20 (11)	C14—C13—C12	119.15 (13)
N2—C4—N1	118.31 (11)	C14—C13—H13	120.4
F2—C5—F1	107.99 (10)	C12—C13—H13	120.4
F2—C5—F3	106.92 (10)	C13—C14—C9	121.39 (12)
F1—C5—F3	107.15 (10)	C13—C14—H14	119.3
F2—C5—C1	111.86 (10)	C9—C14—H14	119.3
F1—C5—C1	110.74 (10)

C4—N1—C1—O1	98.15 (14)	O1—C1—C5—F3	−176.35 (10)
C4—N1—C1—C2	−24.26 (16)	N1—C1—C5—F3	61.24 (13)
C4—N1—C1—C5	−142.52 (11)	C2—C1—C5—F3	−56.12 (13)
O1—C1—C2—C6	49.05 (14)	C7—O4—C6—O3	−13.82 (17)
N1—C1—C2—C6	173.17 (10)	C7—O4—C6—C2	160.62 (10)
C5—C1—C2—C6	−69.90 (13)	C1—C2—C6—O3	−60.93 (16)
O1—C1—C2—C3	−72.30 (12)	C3—C2—C6—O3	62.31 (15)
N1—C1—C2—C3	51.82 (13)	C1—C2—C6—O4	124.72 (11)
C5—C1—C2—C3	168.75 (9)	C3—C2—C6—O4	−112.04 (11)
C4—N2—C3—C9	158.86 (11)	C6—O4—C7—C8	176.95 (10)
C4—N2—C3—C2	38.09 (16)	N2—C3—C9—C14	−51.23 (16)
C6—C2—C3—N2	174.26 (10)	C2—C3—C9—C14	66.90 (14)
C1—C2—C3—N2	−58.11 (12)	N2—C3—C9—C10	132.13 (12)
C6—C2—C3—C9	53.45 (12)	C2—C3—C9—C10	−109.73 (13)
C1—C2—C3—C9	−178.92 (9)	C14—C9—C10—O5	−177.92 (11)
C3—N2—C4—O2	171.65 (11)	C3—C9—C10—O5	−1.22 (17)
C3—N2—C4—N1	−10.02 (18)	C14—C9—C10—C11	1.67 (18)
C1—N1—C4—O2	−179.52 (11)	C3—C9—C10—C11	178.36 (11)
C1—N1—C4—N2	2.12 (18)	O5—C10—C11—C12	178.89 (12)
O1—C1—C5—F2	63.67 (12)	C9—C10—C11—C12	−0.68 (19)
N1—C1—C5—F2	−58.74 (13)	C10—C11—C12—C13	−0.5 (2)
C2—C1—C5—F2	−176.10 (9)	C11—C12—C13—C14	0.7 (2)
O1—C1—C5—F1	−56.85 (13)	C12—C13—C14—C9	0.3 (2)
N1—C1—C5—F1	−179.26 (10)	C10—C9—C14—C13	−1.49 (19)
C2—C1—C5—F1	63.38 (12)	C3—C9—C14—C13	−178.16 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H4···O1ⁱ	0.836 (14)	2.244 (14)	3.0760 (13)	174.1 (14)
N2—H5···O2ⁱⁱ	0.867 (14)	2.040 (15)	2.9064 (14)	177.4 (13)
O1—H1···O5ⁱ	0.858 (17)	2.588 (16)	3.0983 (13)	119.2 (13)
O1—H1···O3ⁱ	0.858 (17)	2.013 (17)	2.8232 (13)	157.1 (15)
O5—H6···O2ⁱⁱⁱ	0.912 (16)	1.759 (17)	2.6685 (12)	175.8 (14)

Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) −x+1, −y, −z+2; (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅F₃N₂O₅
M_r	348.28
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	12.0940 (15), 8.665 (1), 14.3110 (18)
β (°)	93.987 (6)
V (Å³)	1496.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.26 × 0.22 × 0.20

Data collection
Diffractometer	Rigaku Saturn724 CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2009)
T_min, T_max	0.965, 0.973
No. of measured, independent and observed [I > 2σ(I)'] reflections	15222, 3558, 2461
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.075, 0.96
No. of reflections	3558
No. of parameters	234
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.17

Computer programs: CrystalClear-SM Expert (Rigaku, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H4···O1ⁱ	0.836 (14)	2.244 (14)	3.0760 (13)	174.1 (14)
N2—H5···O2ⁱⁱ	0.867 (14)	2.040 (15)	2.9064 (14)	177.4 (13)
O1—H1···O5ⁱ	0.858 (17)	2.588 (16)	3.0983 (13)	119.2 (13)
O1—H1···O3ⁱ	0.858 (17)	2.013 (17)	2.8232 (13)	157.1 (15)
O5—H6···O2ⁱⁱⁱ	0.912 (16)	1.759 (17)	2.6685 (12)	175.8 (14)

Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) −x+1, −y, −z+2; (iii) x, y+1, z.

Acknowledgements

This work was supported by 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

Brier, S., Lemaire, D., DeBonis, S., Forest, E. & Kozielski, F. (2004). Biochemistry, 43, 13072–13082. Web of Science CrossRef PubMed CAS Google Scholar
Cochran, J. C., Gatial, J. E., Kapoor, T. M. & Gilbert, S. P. (2005). J. Biol. Chem. 280, 12658–12667. Web of Science CrossRef PubMed CAS Google Scholar
Hermann, B., Erwin, H. & Hansjorg, K. (2003). US Patent No. 2 003 176 284. Google Scholar
Moran, M. M., Fanger, C., Chong, J. A., McNamara, C., Zhen, X. G. & Mandel-Brehm, J. (2007). WO Patent No. 2 007 073 505. Google Scholar
Rigaku (2009). CrystalClear-SM Expert and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ulrich, H. (2004). US Patent No. 2 004 033 897. Google Scholar
Zorkun, I. S., Sarac, S., Celebi, S. & Erol, K. (2006). Bioorg. Med. Chem. 14, 8582–8589. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 66| Part 7| July 2010| Page o1651

doi:10.1107/S1600536810021355

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rac-Ethyl 4-hy­dr­oxy-6-(2-hy­dr­oxy­phen­yl)-2-oxo-4-(tri­fluoro­methyl)per­hydro­pyrimidine-5-carboxyl­ate

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rac-Ethyl 4-hydroxy-6-(2-hydroxyphenyl)-2-oxo-4-(trifluoromethyl)perhydropyrimidine-5-carboxylate