6-Hy-droxy-4-(pyridin-3-yl)-5-(2-thienyl-carbon-yl)-6-trifluoro-meth-yl-3,4,5,6-tetra-hydro-pyrimidin-2(1H)-one.

In the title compound, C(15)H(12)F(3)N(3)O(3)S, the pyrimidine ring adopts a half-chair conformation with the mean plane formed by the ring atoms excluding the C atom bonded to thio-phene-2-carbonyl group lying nearly perpendicular to the pyridine and thio-phene rings, making dihedral angles of 84.91 (4) and 87.40 (5)°, respectively. The dihedral angle between the pyridine and thio-phene rings is 54.44 (5)°. The crystal structure is stabilized by inter-molecular O-H⋯O and N-H⋯N hydrogen bonds and weak C-H⋯O inter-actions further consolidate the structure.

Related literature

For the bioactivity of dihydro­pyrimidines, see: Cochran et al. (2005 ▶); Moran et al. (2007 ▶); Zorkun et al. (2006 ▶). For the bioactivity of organofluorine compounds, see: Ulrich (2004 ▶). For a related stucture, see: Yang et al. (2009 ▶).

Experimental

Crystal data

C15H12F3N3O3S

M = 371.34

Monoclinic,

a = 29.694 (3) Å

b = 5.9710 (8) Å

c = 17.6910 (16) Å

β = 95.223 (8)°

V = 3123.6 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.26 mm−1

T = 113 K

0.26 × 0.22 × 0.20 mm

Data collection

Rigaku Saturn724 CCD diffractometer

Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku/MSC, 2009 ▶) T min = 0.935, T max = 0.950

15077 measured reflections

3707 independent reflections

2888 reflections with I > 2.0 σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.098

S = 1.04

3707 reflections

238 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku/MSC, 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/MSC, 2009 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810041085/pv2334sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041085/pv2334Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H12F3N3O3S	F(000) = 1520
Mr = 371.34	Dx = 1.579 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -C 2yc	Cell parameters from 5438 reflections
a = 29.694 (3) Å	θ = 1.7–28.0°
b = 5.9710 (8) Å	µ = 0.26 mm−1
c = 17.6910 (16) Å	T = 113 K
β = 95.223 (8)°	Prism, colorless
V = 3123.6 (6) Å3	0.26 × 0.22 × 0.20 mm
Z = 8

Rigaku Saturn724 CCD diffractometer	3707 independent reflections
Radiation source: rotating anode	2888 reflections with I > 2.0 σ(I)
multilayer	Rint = 0.056
Detector resolution: 14.222 pixels mm-1	θmax = 27.9°, θmin = 2.3°
ω scans	h = −38→37
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku/MSC, 2009)	k = −7→7
Tmin = 0.935, Tmax = 0.950	l = −23→23
15077 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0496P)2] where P = (Fo2 + 2Fc2)/3
3707 reflections	(Δ/σ)max = 0.001
238 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.026595 (14)	0.12707 (8)	0.92814 (2)	0.03528 (14)
F1	0.10963 (3)	−0.11784 (17)	0.62064 (4)	0.0313 (2)
F2	0.06951 (3)	−0.11496 (17)	0.71617 (5)	0.0298 (2)
F3	0.09202 (3)	0.19531 (16)	0.67005 (5)	0.0302 (2)
O1	0.15452 (3)	−0.25213 (17)	0.75794 (5)	0.0181 (2)
O2	0.25389 (3)	0.21588 (17)	0.70458 (5)	0.0176 (2)
O3	0.10702 (3)	−0.12933 (18)	0.89515 (5)	0.0238 (2)
N1	0.18320 (4)	0.0743 (2)	0.70261 (6)	0.0155 (3)
N2	0.21958 (4)	0.2166 (2)	0.81451 (6)	0.0153 (3)
N3	0.19968 (4)	0.2310 (2)	1.07057 (6)	0.0179 (3)
C1	0.14728 (4)	−0.0243 (2)	0.74123 (7)	0.0146 (3)
C2	0.22112 (4)	0.1687 (2)	0.74020 (7)	0.0143 (3)
C3	0.18652 (4)	0.1181 (2)	0.86052 (7)	0.0136 (3)
H3	0.1952	−0.0410	0.8719	0.016*
C4	0.14098 (4)	0.1215 (2)	0.81197 (7)	0.0141 (3)
H4	0.1345	0.2788	0.7949	0.017*
C5	0.10424 (5)	−0.0160 (3)	0.68637 (7)	0.0211 (3)
C6	0.18514 (4)	0.2436 (2)	0.93467 (7)	0.0144 (3)
C7	0.16718 (4)	0.4565 (3)	0.93907 (7)	0.0178 (3)
H7	0.1565	0.5349	0.8943	0.021*
C8	0.16500 (5)	0.5540 (3)	1.01013 (7)	0.0208 (3)
H8	0.1524	0.6990	1.0148	0.025*
C9	0.18153 (5)	0.4355 (3)	1.07377 (7)	0.0201 (3)
H9	0.1799	0.5025	1.1222	0.024*
C10	0.20114 (4)	0.1383 (2)	1.00190 (7)	0.0153 (3)
H10	0.2138	−0.0072	0.9990	0.018*
C11	0.10371 (4)	0.0461 (3)	0.85989 (7)	0.0168 (3)
C12	0.06578 (5)	0.1986 (3)	0.86639 (7)	0.0206 (3)
C13	0.05608 (5)	0.4038 (3)	0.83352 (9)	0.0255 (3)
H13	0.0738	0.4723	0.7978	0.031*
C14	0.01670 (5)	0.5012 (3)	0.85897 (10)	0.0372 (4)
H14	0.0049	0.6425	0.8423	0.045*
C15	−0.00227 (5)	0.3696 (3)	0.90984 (10)	0.0404 (5)
H15	−0.0289	0.4088	0.9328	0.048*
H1	0.1888 (5)	0.007 (3)	0.6611 (9)	0.024 (4)*
H2	0.2439 (5)	0.260 (3)	0.8390 (9)	0.020 (4)*
H5	0.1814 (6)	−0.273 (3)	0.7674 (10)	0.031 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.0254 (2)	0.0467 (3)	0.0363 (2)	−0.00599 (19)	0.01643 (16)	−0.00842 (19)
F1	0.0228 (4)	0.0510 (7)	0.0189 (4)	0.0021 (4)	−0.0042 (3)	−0.0141 (4)
F2	0.0159 (4)	0.0449 (7)	0.0283 (5)	−0.0080 (4)	0.0001 (3)	−0.0047 (4)
F3	0.0265 (5)	0.0355 (6)	0.0266 (4)	0.0091 (4)	−0.0088 (3)	0.0028 (4)
O1	0.0159 (5)	0.0168 (6)	0.0216 (5)	−0.0013 (4)	0.0015 (4)	−0.0016 (4)
O2	0.0170 (5)	0.0202 (6)	0.0161 (4)	−0.0023 (4)	0.0039 (3)	0.0002 (4)
O3	0.0260 (5)	0.0226 (6)	0.0233 (5)	−0.0020 (4)	0.0059 (4)	0.0052 (4)
N1	0.0154 (5)	0.0206 (7)	0.0107 (5)	−0.0008 (5)	0.0019 (4)	−0.0017 (4)
N2	0.0140 (6)	0.0198 (7)	0.0121 (5)	−0.0037 (5)	0.0005 (4)	−0.0012 (4)
N3	0.0187 (6)	0.0215 (7)	0.0133 (5)	−0.0030 (5)	0.0008 (4)	0.0005 (5)
C1	0.0137 (6)	0.0152 (8)	0.0147 (6)	0.0003 (5)	0.0002 (4)	−0.0008 (5)
C2	0.0163 (6)	0.0119 (7)	0.0146 (6)	0.0006 (5)	0.0005 (5)	0.0010 (5)
C3	0.0150 (6)	0.0140 (7)	0.0119 (6)	−0.0006 (5)	0.0013 (4)	0.0006 (5)
C4	0.0135 (6)	0.0150 (8)	0.0137 (6)	0.0001 (5)	0.0011 (5)	0.0003 (5)
C5	0.0180 (7)	0.0274 (9)	0.0176 (6)	0.0000 (6)	−0.0003 (5)	−0.0035 (6)
C6	0.0143 (6)	0.0151 (8)	0.0137 (6)	−0.0026 (6)	0.0016 (4)	−0.0005 (5)
C7	0.0209 (7)	0.0178 (8)	0.0146 (6)	−0.0008 (6)	0.0011 (5)	0.0015 (5)
C8	0.0257 (7)	0.0166 (8)	0.0201 (6)	−0.0006 (6)	0.0031 (5)	−0.0027 (5)
C9	0.0237 (7)	0.0222 (9)	0.0146 (6)	−0.0025 (6)	0.0029 (5)	−0.0033 (5)
C10	0.0144 (6)	0.0162 (8)	0.0155 (6)	−0.0013 (5)	0.0024 (5)	0.0008 (5)
C11	0.0165 (6)	0.0191 (8)	0.0147 (6)	−0.0028 (6)	0.0009 (5)	−0.0023 (5)
C12	0.0152 (7)	0.0270 (9)	0.0197 (6)	−0.0026 (6)	0.0024 (5)	−0.0057 (6)
C13	0.0197 (7)	0.0257 (9)	0.0307 (8)	0.0054 (7)	0.0006 (6)	−0.0044 (6)
C14	0.0235 (8)	0.0365 (12)	0.0499 (10)	0.0109 (8)	−0.0060 (7)	−0.0172 (8)
C15	0.0178 (8)	0.0559 (14)	0.0483 (10)	−0.0007 (8)	0.0075 (7)	−0.0310 (9)

S1—C15	1.699 (2)	C3—C4	1.5345 (17)
S1—C12	1.7208 (15)	C3—H3	1.0000
F1—C5	1.3347 (15)	C4—C11	1.5222 (17)
F2—C5	1.3379 (16)	C4—H4	1.0000
F3—C5	1.3370 (18)	C6—C7	1.383 (2)
O1—C1	1.4047 (17)	C6—C10	1.3902 (17)
O1—H5	0.81 (2)	C7—C8	1.3922 (18)
O2—C2	1.2390 (16)	C7—H7	0.9500
O3—C11	1.2187 (17)	C8—C9	1.3813 (19)
N1—C2	1.3753 (17)	C8—H8	0.9500
N1—C1	1.4435 (17)	C9—H9	0.9500
N1—H1	0.87 (2)	C10—H10	0.9500
N2—C2	1.3501 (16)	C11—C12	1.461 (2)
N2—C3	1.4553 (16)	C12—C13	1.375 (2)
N2—H2	0.85 (2)	C13—C14	1.416 (2)
N3—C9	1.3379 (19)	C13—H13	0.9500
N3—C10	1.3393 (16)	C14—C15	1.355 (3)
C1—C5	1.5337 (18)	C14—H14	0.9500
C1—C4	1.5495 (17)	C15—H15	0.9500
C3—C6	1.5145 (17)
C15—S1—C12	91.49 (9)	F1—C5—C1	112.19 (11)
C1—O1—H5	108.7 (13)	F3—C5—C1	111.18 (12)
C2—N1—C1	123.09 (10)	F2—C5—C1	111.36 (11)
C2—N1—H1	112.9 (10)	C7—C6—C10	118.08 (12)
C1—N1—H1	114.8 (11)	C7—C6—C3	122.98 (11)
C2—N2—C3	122.91 (11)	C10—C6—C3	118.90 (12)
C2—N2—H2	117.3 (11)	C6—C7—C8	119.02 (12)
C3—N2—H2	115.1 (11)	C6—C7—H7	120.5
C9—N3—C10	117.51 (11)	C8—C7—H7	120.5
O1—C1—N1	112.90 (10)	C9—C8—C7	118.65 (14)
O1—C1—C5	105.49 (11)	C9—C8—H8	120.7
N1—C1—C5	107.24 (10)	C7—C8—H8	120.7
O1—C1—C4	113.67 (10)	N3—C9—C8	123.19 (12)
N1—C1—C4	107.58 (11)	N3—C9—H9	118.4
C5—C1—C4	109.76 (11)	C8—C9—H9	118.4
O2—C2—N2	123.02 (12)	N3—C10—C6	123.54 (13)
O2—C2—N1	119.57 (11)	N3—C10—H10	118.2
N2—C2—N1	117.31 (12)	C6—C10—H10	118.2
N2—C3—C6	110.93 (11)	O3—C11—C12	121.48 (13)
N2—C3—C4	106.64 (10)	O3—C11—C4	120.69 (12)
C6—C3—C4	112.73 (11)	C12—C11—C4	117.68 (13)
N2—C3—H3	108.8	C13—C12—C11	130.93 (13)
C6—C3—H3	108.8	C13—C12—S1	111.21 (11)
C4—C3—H3	108.8	C11—C12—S1	117.77 (11)
C11—C4—C3	109.42 (10)	C12—C13—C14	112.26 (16)
C11—C4—C1	115.54 (11)	C12—C13—H13	123.9
C3—C4—C1	106.24 (10)	C14—C13—H13	123.9
C11—C4—H4	108.5	C15—C14—C13	112.22 (17)
C3—C4—H4	108.5	C15—C14—H14	123.9
C1—C4—H4	108.5	C13—C14—H14	123.9
F1—C5—F3	107.07 (11)	C14—C15—S1	112.82 (13)
F1—C5—F2	107.45 (12)	C14—C15—H15	123.6
F3—C5—F2	107.35 (11)	S1—C15—H15	123.6
C2—N1—C1—O1	−88.51 (15)	N2—C3—C6—C7	71.30 (16)
C2—N1—C1—C5	155.73 (13)	C4—C3—C6—C7	−48.22 (17)
C2—N1—C1—C4	37.72 (17)	N2—C3—C6—C10	−111.02 (13)
C3—N2—C2—O2	−165.46 (13)	C4—C3—C6—C10	129.46 (13)
C3—N2—C2—N1	18.18 (19)	C10—C6—C7—C8	−1.32 (19)
C1—N1—C2—O2	167.89 (12)	C3—C6—C7—C8	176.37 (12)
C1—N1—C2—N2	−15.6 (2)	C6—C7—C8—C9	1.0 (2)
C2—N2—C3—C6	−165.76 (12)	C10—N3—C9—C8	−0.8 (2)
C2—N2—C3—C4	−42.66 (17)	C7—C8—C9—N3	0.1 (2)
N2—C3—C4—C11	−173.34 (11)	C9—N3—C10—C6	0.38 (19)
C6—C3—C4—C11	−51.37 (15)	C7—C6—C10—N3	0.7 (2)
N2—C3—C4—C1	61.28 (13)	C3—C6—C10—N3	−177.13 (12)
C6—C3—C4—C1	−176.75 (11)	C3—C4—C11—O3	−52.53 (17)
O1—C1—C4—C11	−55.20 (14)	C1—C4—C11—O3	67.28 (16)
N1—C1—C4—C11	179.03 (10)	C3—C4—C11—C12	123.10 (12)
C5—C1—C4—C11	62.66 (15)	C1—C4—C11—C12	−117.09 (13)
O1—C1—C4—C3	66.33 (13)	O3—C11—C12—C13	178.48 (14)
N1—C1—C4—C3	−59.43 (13)	C4—C11—C12—C13	2.9 (2)
C5—C1—C4—C3	−175.80 (11)	O3—C11—C12—S1	2.12 (18)
O1—C1—C5—F1	−64.29 (14)	C4—C11—C12—S1	−173.47 (9)
N1—C1—C5—F1	56.29 (16)	C15—S1—C12—C13	0.00 (12)
C4—C1—C5—F1	172.87 (12)	C15—S1—C12—C11	177.05 (11)
O1—C1—C5—F3	175.84 (10)	C11—C12—C13—C14	−176.56 (14)
N1—C1—C5—F3	−63.58 (14)	S1—C12—C13—C14	−0.02 (16)
C4—C1—C5—F3	53.01 (15)	C12—C13—C14—C15	0.03 (19)
O1—C1—C5—F2	56.18 (14)	C13—C14—C15—S1	−0.04 (18)
N1—C1—C5—F2	176.76 (11)	C12—S1—C15—C14	0.02 (13)
C4—C1—C5—F2	−66.65 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H5···O2i	0.81 (2)	1.94 (2)	2.7466 (14)	173 (2)
N2—H2···N3ii	0.85 (2)	2.21 (2)	3.0153 (15)	159 (2)
N1—H1···N3iii	0.87 (2)	2.19 (2)	3.0378 (16)	167 (2)
C3—H3···O1	1.00	2.58	2.961 (2)	102
C3—H3···O2i	1.00	2.57	3.255 (2)	126
C7—H7···O3iv	0.95	2.49	3.108 (2)	123

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H5⋯O2i	0.81 (2)	1.94 (2)	2.7466 (14)	173 (2)
N2—H2⋯N3ii	0.85 (2)	2.21 (2)	3.0153 (15)	159 (2)
N1—H1⋯N3iii	0.87 (2)	2.19 (2)	3.0378 (16)	167 (2)
C3—H3⋯O2i	1.00	2.57	3.255 (2)	126
C7—H7⋯O3iv	0.95	2.49	3.108 (2)	123

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .