4-(3-Fluoro-phen-yl)-6-hy-droxy-5-(thio-phen-2-ylcarbon-yl)-6-trifluoro-methyl-1,3-diazinan-2-one.

In the title compound, C(16)H(12)F(4)N(2)O(3)S, the pyrimidine ring adopts a half-chair conformation; the mean plane formed by the ring atoms excluding the C atom bonded to the thio-phen-2-ylcarbonyl group has an r.m.s. deviation of 0.059 Å. The dihedral angle between the benzene and thio-phene rings is 62.26 (7)°. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯O hydrogen bond, generating an S(6) ring. In the crystal, adjacent mol-ecules are connected via a centrosymmetric R(2) (2)(6) motif, formed by N-H⋯O hydrogen bonds.

Related literature

For the bioactivity of dihydro­pyrimidines, see: Cochran et al. (2005 ▶); Zorkun et al. (2006 ▶); Moran et al. (2007 ▶). For the bioactivity of organofluorine compounds, see: Hermann et al. (2003 ▶); Ulrich (2004 ▶). For a related structure, see: Mosslemin et al. (2009 ▶).

Experimental

Crystal data

C16H12F4N2O3S

M = 388.34

Triclinic,

a = 6.6032 (10) Å

b = 10.4541 (16) Å

c = 12.4906 (18) Å

α = 77.136 (12)°

β = 78.940 (13)°

γ = 72.839 (11)°

V = 795.8 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.27 mm−1

T = 113 K

0.18 × 0.06 × 0.06 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2009 ▶) T min = 0.953, T max = 0.984

10393 measured reflections

3784 independent reflections

2531 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.082

S = 0.95

3784 reflections

247 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrystalClear (Rigaku, 2009 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811006933/nk2083sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006933/nk2083Isup2.hkl

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

C16H12F4N2O3S	Z = 2
Mr = 388.34	F(000) = 396
Triclinic, P1	Dx = 1.621 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6032 (10) Å	Cell parameters from 3248 reflections
b = 10.4541 (16) Å	θ = 1.7–31.2°
c = 12.4906 (18) Å	µ = 0.27 mm−1
α = 77.136 (12)°	T = 113 K
β = 78.940 (13)°	Prism, colourless
γ = 72.839 (11)°	0.18 × 0.06 × 0.06 mm
V = 795.8 (2) Å3

Rigaku Saturn CCD area-detector diffractometer	3784 independent reflections
Radiation source: rotating anode	2531 reflections with I > 2σ(I)
multilayer	Rint = 0.045
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 1.7°
ω and φ scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2009)	k = −13→13
Tmin = 0.953, Tmax = 0.984	l = −16→16
10393 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ2(Fo2) + (0.0352P)2] where P = (Fo2 + 2Fc2)/3
3784 reflections	(Δ/σ)max = 0.001
247 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.24 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	0.10178 (8)	0.67205 (5)	0.43354 (4)	0.02686 (14)
F1	0.54415 (17)	0.42910 (11)	0.11049 (10)	0.0313 (3)
F2	0.38941 (17)	1.06273 (11)	0.41921 (8)	0.0275 (3)
F3	0.26149 (16)	1.25835 (10)	0.32224 (9)	0.0227 (3)
F4	0.09036 (16)	1.10363 (11)	0.35651 (9)	0.0267 (3)
O1	0.15491 (18)	0.87185 (12)	0.22648 (10)	0.0199 (3)
O2	0.2727 (2)	1.13183 (13)	0.14128 (10)	0.0167 (3)
H2	0.178 (3)	1.097 (2)	0.1497 (18)	0.036 (7)*
O3	0.89825 (18)	1.13035 (12)	0.07872 (10)	0.0176 (3)
N1	0.7582 (2)	0.95351 (15)	0.08904 (13)	0.0146 (3)
N2	0.5923 (2)	1.12219 (16)	0.19491 (12)	0.0153 (3)
C1	0.1989 (3)	0.5998 (2)	0.55599 (16)	0.0278 (5)
H1A	0.1369	0.5394	0.6120	0.033*
C2	0.3737 (3)	0.63720 (19)	0.56549 (16)	0.0254 (5)
H2B	0.4474	0.6065	0.6286	0.031*
C3	0.4332 (3)	0.72758 (18)	0.46990 (15)	0.0198 (4)
H3	0.5523	0.7640	0.4615	0.024*
C4	0.3001 (3)	0.75680 (18)	0.39064 (15)	0.0174 (4)
C5	0.2979 (3)	0.84873 (17)	0.28367 (15)	0.0152 (4)
C6	0.4813 (3)	0.91633 (17)	0.24203 (14)	0.0131 (4)
H6	0.5862	0.8833	0.2966	0.016*
C7	0.4045 (3)	1.07322 (17)	0.22502 (14)	0.0130 (4)
C8	0.7569 (3)	1.07005 (17)	0.11741 (14)	0.0140 (4)
C9	0.5952 (3)	0.87853 (17)	0.12902 (14)	0.0130 (4)
H9	0.4880	0.9089	0.0757	0.016*
C10	0.6952 (3)	0.72647 (17)	0.13508 (14)	0.0135 (4)
C11	0.5744 (3)	0.64573 (18)	0.11689 (15)	0.0161 (4)
H11	0.4320	0.6846	0.1005	0.019*
C12	0.6671 (3)	0.50868 (18)	0.12332 (15)	0.0187 (4)
C13	0.8746 (3)	0.44660 (18)	0.14207 (15)	0.0196 (4)
H13	0.9345	0.3518	0.1434	0.024*
C14	0.9932 (3)	0.52851 (18)	0.15906 (15)	0.0203 (4)
H14	1.1375	0.4893	0.1722	0.024*
C15	0.9039 (3)	0.66661 (18)	0.15703 (14)	0.0168 (4)
H15	0.9860	0.7207	0.1708	0.020*
C16	0.2862 (3)	1.12363 (18)	0.33183 (15)	0.0174 (4)
H2A	0.572 (3)	1.207 (2)	0.1936 (16)	0.021 (5)*
H1	0.862 (3)	0.9241 (19)	0.0400 (16)	0.023 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0281 (3)	0.0272 (3)	0.0271 (3)	−0.0167 (2)	0.0034 (2)	−0.0019 (2)
F1	0.0319 (7)	0.0164 (6)	0.0517 (8)	−0.0106 (5)	−0.0110 (6)	−0.0081 (5)
F2	0.0390 (7)	0.0251 (6)	0.0174 (6)	−0.0029 (5)	−0.0083 (5)	−0.0050 (5)
F3	0.0261 (6)	0.0143 (5)	0.0276 (6)	−0.0042 (5)	0.0008 (5)	−0.0086 (5)
F4	0.0218 (6)	0.0281 (6)	0.0318 (6)	−0.0120 (5)	0.0092 (5)	−0.0122 (5)
O1	0.0183 (7)	0.0207 (7)	0.0236 (7)	−0.0083 (6)	−0.0065 (6)	−0.0020 (6)
O2	0.0158 (7)	0.0149 (7)	0.0209 (7)	−0.0060 (6)	−0.0054 (6)	−0.0011 (5)
O3	0.0141 (6)	0.0139 (6)	0.0258 (7)	−0.0070 (5)	0.0009 (5)	−0.0041 (6)
N1	0.0133 (8)	0.0118 (8)	0.0193 (8)	−0.0052 (6)	0.0008 (7)	−0.0041 (6)
N2	0.0151 (8)	0.0112 (8)	0.0208 (8)	−0.0045 (7)	−0.0011 (6)	−0.0052 (7)
C1	0.0352 (12)	0.0204 (10)	0.0217 (10)	−0.0081 (9)	0.0087 (9)	−0.0009 (8)
C2	0.0341 (12)	0.0215 (10)	0.0170 (10)	−0.0047 (9)	−0.0016 (9)	−0.0008 (8)
C3	0.0221 (10)	0.0180 (10)	0.0191 (10)	−0.0067 (8)	−0.0010 (8)	−0.0023 (8)
C4	0.0178 (9)	0.0158 (9)	0.0189 (9)	−0.0069 (8)	0.0029 (8)	−0.0052 (8)
C5	0.0156 (9)	0.0122 (9)	0.0187 (9)	−0.0042 (8)	0.0017 (8)	−0.0070 (7)
C6	0.0123 (9)	0.0115 (9)	0.0161 (9)	−0.0039 (7)	−0.0028 (7)	−0.0020 (7)
C7	0.0143 (9)	0.0114 (8)	0.0149 (9)	−0.0049 (7)	−0.0039 (7)	−0.0021 (7)
C8	0.0136 (9)	0.0115 (9)	0.0167 (9)	−0.0028 (7)	−0.0062 (7)	0.0005 (7)
C9	0.0127 (9)	0.0118 (9)	0.0159 (9)	−0.0066 (7)	−0.0012 (7)	−0.0017 (7)
C10	0.0172 (9)	0.0114 (9)	0.0118 (8)	−0.0048 (8)	−0.0007 (7)	−0.0014 (7)
C11	0.0147 (9)	0.0137 (9)	0.0205 (9)	−0.0042 (7)	−0.0034 (8)	−0.0029 (7)
C12	0.0243 (10)	0.0157 (9)	0.0211 (10)	−0.0124 (8)	−0.0032 (8)	−0.0036 (8)
C13	0.0233 (10)	0.0116 (9)	0.0198 (10)	−0.0019 (8)	0.0011 (8)	−0.0010 (8)
C14	0.0162 (10)	0.0177 (10)	0.0242 (10)	−0.0024 (8)	−0.0034 (8)	0.0001 (8)
C15	0.0179 (10)	0.0153 (9)	0.0182 (9)	−0.0068 (8)	−0.0039 (8)	−0.0002 (8)
C16	0.0177 (10)	0.0124 (9)	0.0220 (10)	−0.0041 (8)	−0.0026 (8)	−0.0028 (8)

S1—C1	1.702 (2)	C3—C4	1.374 (2)
S1—C4	1.7293 (18)	C3—H3	0.9500
F1—C12	1.3730 (19)	C4—C5	1.462 (2)
F2—C16	1.335 (2)	C5—C6	1.528 (2)
F3—C16	1.3495 (19)	C6—C9	1.543 (2)
F4—C16	1.3372 (19)	C6—C7	1.545 (2)
O1—C5	1.228 (2)	C6—H6	1.0000
O2—C7	1.406 (2)	C7—C16	1.529 (2)
O2—H2	0.79 (2)	C9—C10	1.521 (2)
O3—C8	1.2414 (19)	C9—H9	1.0000
N1—C8	1.340 (2)	C10—C15	1.388 (2)
N1—C9	1.462 (2)	C10—C11	1.397 (2)
N1—H1	0.858 (19)	C11—C12	1.373 (2)
N2—C8	1.377 (2)	C11—H11	0.9500
N2—C7	1.433 (2)	C12—C13	1.372 (2)
N2—H2A	0.855 (19)	C13—C14	1.390 (2)
C1—C2	1.356 (3)	C13—H13	0.9500
C1—H1A	0.9500	C14—C15	1.386 (2)
C2—C3	1.417 (2)	C14—H14	0.9500
C2—H2B	0.9500	C15—H15	0.9500
C1—S1—C4	91.22 (10)	C16—C7—C6	111.98 (14)
C7—O2—H2	111.1 (16)	O3—C8—N1	123.00 (17)
C8—N1—C9	126.08 (16)	O3—C8—N2	119.39 (16)
C8—N1—H1	115.4 (13)	N1—C8—N2	117.60 (16)
C9—N1—H1	118.4 (13)	N1—C9—C10	110.62 (14)
C8—N2—C7	121.26 (15)	N1—C9—C6	107.74 (14)
C8—N2—H2A	113.8 (13)	C10—C9—C6	112.89 (14)
C7—N2—H2A	115.5 (12)	N1—C9—H9	108.5
C2—C1—S1	113.23 (15)	C10—C9—H9	108.5
C2—C1—H1A	123.4	C6—C9—H9	108.5
S1—C1—H1A	123.4	C15—C10—C11	119.36 (16)
C1—C2—C3	111.78 (18)	C15—C10—C9	121.52 (15)
C1—C2—H2B	124.1	C11—C10—C9	119.11 (15)
C3—C2—H2B	124.1	C12—C11—C10	118.21 (16)
C4—C3—C2	112.76 (17)	C12—C11—H11	120.9
C4—C3—H3	123.6	C10—C11—H11	120.9
C2—C3—H3	123.6	C13—C12—C11	123.99 (17)
C3—C4—C5	130.49 (16)	C13—C12—F1	118.16 (16)
C3—C4—S1	111.01 (14)	C11—C12—F1	117.84 (16)
C5—C4—S1	118.45 (14)	C12—C13—C14	117.07 (17)
O1—C5—C4	121.99 (16)	C12—C13—H13	121.5
O1—C5—C6	119.49 (16)	C14—C13—H13	121.5
C4—C5—C6	118.52 (15)	C15—C14—C13	120.89 (17)
C5—C6—C9	109.89 (14)	C15—C14—H14	119.6
C5—C6—C7	112.76 (14)	C13—C14—H14	119.6
C9—C6—C7	106.99 (13)	C14—C15—C10	120.42 (17)
C5—C6—H6	109.0	C14—C15—H15	119.8
C9—C6—H6	109.0	C10—C15—H15	119.8
C7—C6—H6	109.0	F2—C16—F4	107.48 (14)
O2—C7—N2	108.42 (14)	F2—C16—F3	106.62 (15)
O2—C7—C16	108.32 (14)	F4—C16—F3	106.94 (14)
N2—C7—C16	107.11 (14)	F2—C16—C7	112.78 (14)
O2—C7—C6	113.95 (14)	F4—C16—C7	111.68 (15)
N2—C7—C6	106.77 (14)	F3—C16—C7	111.02 (14)
C4—S1—C1—C2	0.06 (16)	C8—N1—C9—C6	−24.5 (2)
S1—C1—C2—C3	−0.2 (2)	C5—C6—C9—N1	175.83 (13)
C1—C2—C3—C4	0.4 (2)	C7—C6—C9—N1	53.10 (17)
C2—C3—C4—C5	176.81 (18)	C5—C6—C9—C10	−61.73 (18)
C2—C3—C4—S1	−0.3 (2)	C7—C6—C9—C10	175.53 (13)
C1—S1—C4—C3	0.16 (15)	N1—C9—C10—C15	30.8 (2)
C1—S1—C4—C5	−177.37 (15)	C6—C9—C10—C15	−90.03 (19)
C3—C4—C5—O1	−173.57 (18)	N1—C9—C10—C11	−148.51 (15)
S1—C4—C5—O1	3.4 (2)	C6—C9—C10—C11	90.68 (19)
C3—C4—C5—C6	7.1 (3)	C15—C10—C11—C12	1.0 (3)
S1—C4—C5—C6	−175.94 (13)	C9—C10—C11—C12	−179.65 (16)
O1—C5—C6—C9	−57.9 (2)	C10—C11—C12—C13	−2.8 (3)
C4—C5—C6—C9	121.40 (17)	C10—C11—C12—F1	177.01 (15)
O1—C5—C6—C7	61.3 (2)	C11—C12—C13—C14	2.2 (3)
C4—C5—C6—C7	−119.34 (17)	F1—C12—C13—C14	−177.57 (16)
C8—N2—C7—O2	−78.04 (19)	C12—C13—C14—C15	0.0 (3)
C8—N2—C7—C16	165.27 (15)	C13—C14—C15—C10	−1.7 (3)
C8—N2—C7—C6	45.1 (2)	C11—C10—C15—C14	1.1 (3)
C5—C6—C7—O2	−64.89 (19)	C9—C10—C15—C14	−178.19 (16)
C9—C6—C7—O2	56.04 (18)	O2—C7—C16—F2	173.58 (13)
C5—C6—C7—N2	175.45 (14)	N2—C7—C16—F2	−69.67 (18)
C9—C6—C7—N2	−63.62 (17)	C6—C7—C16—F2	47.07 (19)
C5—C6—C7—C16	58.50 (19)	O2—C7—C16—F4	52.41 (18)
C9—C6—C7—C16	179.43 (14)	N2—C7—C16—F4	169.17 (13)
C9—N1—C8—O3	−178.49 (15)	C6—C7—C16—F4	−74.09 (18)
C9—N1—C8—N2	2.9 (2)	O2—C7—C16—F3	−66.84 (18)
C7—N2—C8—O3	167.11 (15)	N2—C7—C16—F3	49.92 (18)
C7—N2—C8—N1	−14.3 (2)	C6—C7—C16—F3	166.66 (14)
C8—N1—C9—C10	−148.29 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.79 (2)	2.38 (2)	2.9609 (18)	131.7 (19)
N1—H1···O3i	0.858 (19)	1.99 (2)	2.851 (2)	175.9 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.79 (2)	2.38 (2)	2.9609 (18)	131.7 (19)
N1—H1⋯O3i	0.858 (19)	1.99 (2)	2.851 (2)	175.9 (18)

Symmetry code: (i) .