Ethyl 4-[3,5-bis-(trifluoro-meth-yl)phen-yl]-6-methyl-2-oxo-1,2,3,4-tetra-hydro-pyrimidine-5-carboxyl-ate.

In the title compound, C(16)H(14)F(6)N(2)O(3), the dihydro-pyrimid-in-one ring adopts an envelope conformation. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds into a ribbon-like structure along the b axis. In the ribbon, a pair of bifurcated acceptor N-H⋯O and C-H⋯O bonds generate an R(2) (1)(6) ring motif. Adjacent ribbons are linked via C-H⋯F hydrogen bonds.

Related literature

For general background and the pharmaceutical applications of pyrimidinones, see: Kalluraya & Rai (2003 ▶); Atwal (1990 ▶); Steele et al. (1998 ▶); Manjula et al. (2004 ▶); Matsuda & Hirao (1965 ▶). For a related structure, see: Fun et al. (2009 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H14F6N2O3

M = 396.29

Monoclinic,

a = 12.6876 (2) Å

b = 7.3073 (1) Å

c = 19.9547 (3) Å

β = 114.443 (1)°

V = 1684.23 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.15 mm−1

T = 110 K

0.45 × 0.25 × 0.22 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.908, T max = 0.967

22326 measured reflections

7151 independent reflections

5660 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.134

S = 1.04

7151 reflections

254 parameters

36 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.49 e Å−3

Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809019035/ci2801sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019035/ci2801Isup2.hkl

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

C16H14F6N2O3	F(000) = 808
Mr = 396.29	Dx = 1.563 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9602 reflections
a = 12.6876 (2) Å	θ = 3.2–35.0°
b = 7.3073 (1) Å	µ = 0.15 mm−1
c = 19.9547 (3) Å	T = 110 K
β = 114.443 (1)°	Block, colourless
V = 1684.23 (5) Å3	0.45 × 0.25 × 0.22 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	7151 independent reflections
Radiation source: fine-focus sealed tube	5660 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 35.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −20→20
Tmin = 0.908, Tmax = 0.967	k = −11→11
22326 measured reflections	l = −32→32

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0681P)2 + 0.4398P] where P = (Fo2 + 2Fc2)/3
7151 reflections	(Δ/σ)max = 0.001
254 parameters	Δρmax = 0.49 e Å−3
36 restraints	Δρmin = −0.45 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 110.0 (1) K.

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 > 2sigma(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
F1	1.02153 (7)	1.04916 (15)	0.79988 (6)	0.0546 (3)
F2	1.12550 (8)	0.80663 (18)	0.82674 (7)	0.0625 (3)
F3	1.08940 (8)	0.94509 (16)	0.90918 (5)	0.0510 (3)
F4	0.96398 (11)	0.31292 (16)	0.94197 (6)	0.0734 (4)
F5	0.78290 (13)	0.33990 (15)	0.91770 (7)	0.0721 (4)
F6	0.83618 (9)	0.18885 (11)	0.84630 (5)	0.0416 (2)
O1	0.54733 (7)	1.21425 (11)	0.72029 (5)	0.02532 (16)
O2	0.65993 (7)	0.70237 (10)	0.50892 (4)	0.02120 (15)
O3	0.63160 (7)	0.49775 (10)	0.58404 (4)	0.01973 (14)
N1	0.56554 (7)	0.90955 (12)	0.70349 (5)	0.01736 (15)
H1N1	0.5326 (13)	0.881 (2)	0.7321 (8)	0.024 (4)*
N2	0.62532 (7)	1.12340 (12)	0.64147 (5)	0.01722 (15)
H1N2	0.6307 (13)	1.238 (2)	0.6327 (8)	0.025 (4)*
C1	0.83363 (8)	0.82264 (14)	0.76186 (5)	0.01796 (16)
H1	0.8281	0.9301	0.7338	0.022*
C2	0.93726 (9)	0.77888 (16)	0.82033 (5)	0.02191 (19)
C3	0.94750 (10)	0.62163 (17)	0.86221 (6)	0.0247 (2)
H3	1.0185	0.5927	0.9024	0.030*
C4	0.85233 (10)	0.50878 (15)	0.84400 (5)	0.02311 (19)
C5	0.74728 (9)	0.55033 (14)	0.78490 (5)	0.01934 (17)
H5	0.6829	0.4704	0.7727	0.023*
C6	0.73721 (8)	0.70860 (13)	0.74415 (5)	0.01511 (15)
C7	0.62140 (7)	0.75947 (13)	0.68172 (5)	0.01453 (15)
H7	0.5695	0.6501	0.6705	0.017*
C8	0.57787 (8)	1.08737 (14)	0.69151 (5)	0.01731 (16)
C9	0.64143 (7)	0.99139 (13)	0.59672 (5)	0.01476 (15)
C10	0.63470 (7)	0.81180 (12)	0.61226 (5)	0.01376 (14)
C11	0.64206 (7)	0.65599 (13)	0.56809 (5)	0.01450 (15)
C12	0.66444 (9)	0.55645 (15)	0.46087 (5)	0.02057 (18)
H12A	0.5860	0.5072	0.4317	0.025*
H12B	0.7146	0.4556	0.4900	0.025*
C13	0.71342 (13)	0.64003 (19)	0.41112 (7)	0.0337 (3)
H13A	0.7119	0.5496	0.3745	0.051*
H13B	0.7935	0.6785	0.4404	0.051*
H13C	0.6669	0.7466	0.3861	0.051*
C14	0.66536 (10)	1.06995 (14)	0.53478 (5)	0.02129 (18)
H14A	0.7385	1.0205	0.5369	0.032*
H14B	0.6709	1.2035	0.5394	0.032*
H14C	0.6023	1.0371	0.4876	0.032*
C15	0.85946 (13)	0.33881 (18)	0.88774 (7)	0.0338 (3)
C16	1.04253 (10)	0.8954 (2)	0.83865 (7)	0.0314 (2)

	U11	U22	U33	U12	U13	U23
F1	0.0302 (4)	0.0609 (6)	0.0583 (6)	−0.0195 (4)	0.0037 (4)	0.0275 (5)
F2	0.0249 (4)	0.0770 (8)	0.0886 (8)	−0.0072 (4)	0.0266 (5)	−0.0217 (7)
F3	0.0464 (5)	0.0600 (7)	0.0342 (4)	−0.0237 (5)	0.0044 (4)	−0.0086 (4)
F4	0.0821 (8)	0.0439 (6)	0.0514 (6)	−0.0039 (5)	−0.0152 (5)	0.0284 (5)
F5	0.1372 (11)	0.0420 (6)	0.0831 (8)	0.0306 (6)	0.0916 (9)	0.0335 (6)
F6	0.0642 (6)	0.0183 (4)	0.0462 (5)	0.0014 (4)	0.0267 (4)	0.0044 (3)
O1	0.0308 (4)	0.0193 (4)	0.0354 (4)	0.0011 (3)	0.0233 (3)	−0.0065 (3)
O2	0.0373 (4)	0.0144 (3)	0.0191 (3)	−0.0018 (3)	0.0188 (3)	−0.0016 (3)
O3	0.0293 (3)	0.0120 (3)	0.0219 (3)	−0.0003 (3)	0.0147 (3)	0.0004 (2)
N1	0.0207 (3)	0.0156 (4)	0.0226 (3)	−0.0005 (3)	0.0157 (3)	−0.0004 (3)
N2	0.0235 (4)	0.0112 (3)	0.0226 (3)	−0.0007 (3)	0.0151 (3)	−0.0012 (3)
C1	0.0194 (4)	0.0180 (4)	0.0178 (3)	−0.0003 (3)	0.0091 (3)	0.0019 (3)
C2	0.0198 (4)	0.0257 (5)	0.0193 (4)	0.0002 (4)	0.0072 (3)	0.0008 (4)
C3	0.0265 (5)	0.0266 (5)	0.0185 (4)	0.0059 (4)	0.0069 (3)	0.0033 (4)
C4	0.0358 (5)	0.0166 (4)	0.0181 (4)	0.0036 (4)	0.0123 (4)	0.0029 (3)
C5	0.0284 (4)	0.0149 (4)	0.0176 (4)	−0.0010 (3)	0.0123 (3)	0.0005 (3)
C6	0.0203 (4)	0.0134 (4)	0.0146 (3)	0.0000 (3)	0.0103 (3)	0.0000 (3)
C7	0.0178 (3)	0.0128 (4)	0.0164 (3)	−0.0020 (3)	0.0104 (3)	−0.0009 (3)
C8	0.0175 (4)	0.0165 (4)	0.0218 (4)	−0.0004 (3)	0.0120 (3)	−0.0025 (3)
C9	0.0175 (3)	0.0126 (4)	0.0161 (3)	−0.0003 (3)	0.0088 (3)	−0.0001 (3)
C10	0.0174 (3)	0.0120 (4)	0.0143 (3)	−0.0008 (3)	0.0090 (3)	0.0000 (3)
C11	0.0167 (3)	0.0138 (4)	0.0143 (3)	−0.0002 (3)	0.0077 (3)	0.0001 (3)
C12	0.0268 (4)	0.0195 (4)	0.0191 (4)	−0.0007 (4)	0.0131 (3)	−0.0049 (3)
C13	0.0535 (7)	0.0306 (6)	0.0308 (5)	0.0104 (5)	0.0313 (5)	0.0070 (5)
C14	0.0348 (5)	0.0140 (4)	0.0210 (4)	−0.0005 (4)	0.0175 (4)	0.0021 (3)
C15	0.0523 (7)	0.0227 (6)	0.0262 (5)	0.0061 (5)	0.0159 (5)	0.0083 (4)
C16	0.0201 (4)	0.0404 (7)	0.0290 (5)	−0.0035 (4)	0.0054 (4)	0.0029 (5)

F1—C16	1.3271 (17)	C3—C4	1.3809 (17)
F2—C16	1.3388 (16)	C3—H3	0.95
F3—C16	1.3317 (15)	C4—C5	1.3994 (15)
F4—C15	1.3334 (17)	C4—C15	1.4991 (16)
F5—C15	1.3348 (17)	C5—C6	1.3890 (13)
F6—C15	1.3302 (16)	C5—H5	0.95
O1—C8	1.2344 (11)	C6—C7	1.5278 (13)
O2—C11	1.3350 (10)	C7—C10	1.5129 (11)
O2—C12	1.4508 (12)	C7—H7	1.00
O3—C11	1.2210 (12)	C9—C10	1.3593 (13)
N1—C8	1.3420 (13)	C9—C14	1.5034 (12)
N1—C7	1.4659 (12)	C10—C11	1.4663 (12)
N1—H1N1	0.860 (15)	C12—C13	1.5017 (15)
N2—C9	1.3859 (12)	C12—H12A	0.99
N2—C8	1.3879 (11)	C12—H12B	0.99
N2—H1N2	0.866 (17)	C13—H13A	0.98
C1—C2	1.3867 (14)	C13—H13B	0.98
C1—C6	1.3993 (13)	C13—H13C	0.98
C1—H1	0.95	C14—H14A	0.98
C2—C3	1.3949 (16)	C14—H14B	0.98
C2—C16	1.4961 (16)	C14—H14C	0.98
C11—O2—C12	117.75 (8)	C9—C10—C11	125.94 (8)
C8—N1—C7	124.42 (7)	C9—C10—C7	119.63 (8)
C8—N1—H1N1	118.3 (11)	C11—C10—C7	114.42 (8)
C7—N1—H1N1	116.5 (11)	O3—C11—O2	123.19 (8)
C9—N2—C8	123.71 (8)	O3—C11—C10	122.54 (8)
C9—N2—H1N2	120.0 (10)	O2—C11—C10	114.26 (8)
C8—N2—H1N2	115.0 (10)	O2—C12—C13	106.15 (9)
C2—C1—C6	120.04 (9)	O2—C12—H12A	110.5
C2—C1—H1	120.0	C13—C12—H12A	110.5
C6—C1—H1	120.0	O2—C12—H12B	110.5
C1—C2—C3	120.99 (10)	C13—C12—H12B	110.5
C1—C2—C16	120.94 (10)	H12A—C12—H12B	108.7
C3—C2—C16	118.04 (10)	C12—C13—H13A	109.5
C4—C3—C2	118.67 (9)	C12—C13—H13B	109.5
C4—C3—H3	120.7	H13A—C13—H13B	109.5
C2—C3—H3	120.7	C12—C13—H13C	109.5
C3—C4—C5	121.09 (10)	H13A—C13—H13C	109.5
C3—C4—C15	120.40 (10)	H13B—C13—H13C	109.5
C5—C4—C15	118.51 (11)	C9—C14—H14A	109.5
C6—C5—C4	119.92 (9)	C9—C14—H14B	109.5
C6—C5—H5	120.0	H14A—C14—H14B	109.5
C4—C5—H5	120.0	C9—C14—H14C	109.5
C5—C6—C1	119.28 (9)	H14A—C14—H14C	109.5
C5—C6—C7	120.29 (8)	H14B—C14—H14C	109.5
C1—C6—C7	120.42 (8)	F6—C15—F4	106.15 (12)
N1—C7—C10	109.47 (7)	F6—C15—F5	105.53 (12)
N1—C7—C6	111.10 (7)	F4—C15—F5	107.51 (12)
C10—C7—C6	111.98 (7)	F6—C15—C4	112.10 (10)
N1—C7—H7	108.0	F4—C15—C4	112.97 (12)
C10—C7—H7	108.0	F5—C15—C4	112.09 (11)
C6—C7—H7	108.0	F1—C16—F3	106.23 (12)
O1—C8—N1	124.21 (8)	F1—C16—F2	106.83 (12)
O1—C8—N2	120.35 (9)	F3—C16—F2	106.23 (11)
N1—C8—N2	115.41 (8)	F1—C16—C2	113.32 (10)
C10—C9—N2	119.02 (8)	F3—C16—C2	112.12 (10)
C10—C9—C14	127.54 (8)	F2—C16—C2	111.64 (12)
N2—C9—C14	113.44 (8)
C6—C1—C2—C3	0.11 (15)	N2—C9—C10—C7	−5.85 (13)
C6—C1—C2—C16	177.92 (10)	C14—C9—C10—C7	173.99 (9)
C1—C2—C3—C4	0.49 (16)	N1—C7—C10—C9	26.13 (11)
C16—C2—C3—C4	−177.37 (10)	C6—C7—C10—C9	−97.55 (10)
C2—C3—C4—C5	−0.12 (15)	N1—C7—C10—C11	−155.34 (7)
C2—C3—C4—C15	−179.77 (10)	C6—C7—C10—C11	80.98 (10)
C3—C4—C5—C6	−0.86 (15)	C12—O2—C11—O3	1.37 (14)
C15—C4—C5—C6	178.79 (9)	C12—O2—C11—C10	−177.99 (8)
C4—C5—C6—C1	1.46 (13)	C9—C10—C11—O3	−177.59 (9)
C4—C5—C6—C7	−177.28 (8)	C7—C10—C11—O3	4.00 (13)
C2—C1—C6—C5	−1.09 (14)	C9—C10—C11—O2	1.78 (13)
C2—C1—C6—C7	177.64 (8)	C7—C10—C11—O2	−176.63 (8)
C8—N1—C7—C10	−31.69 (12)	C11—O2—C12—C13	−166.51 (9)
C8—N1—C7—C6	92.51 (11)	C3—C4—C15—F6	−120.88 (13)
C5—C6—C7—N1	104.84 (9)	C5—C4—C15—F6	59.46 (15)
C1—C6—C7—N1	−73.88 (10)	C3—C4—C15—F4	−1.01 (17)
C5—C6—C7—C10	−132.40 (9)	C5—C4—C15—F4	179.34 (11)
C1—C6—C7—C10	48.88 (11)	C3—C4—C15—F5	120.64 (14)
C7—N1—C8—O1	−167.27 (9)	C5—C4—C15—F5	−59.01 (15)
C7—N1—C8—N2	14.68 (14)	C1—C2—C16—F1	7.46 (17)
C9—N2—C8—O1	−167.38 (9)	C3—C2—C16—F1	−174.67 (11)
C9—N2—C8—N1	10.76 (14)	C1—C2—C16—F3	127.71 (12)
C8—N2—C9—C10	−14.76 (14)	C3—C2—C16—F3	−54.42 (16)
C8—N2—C9—C14	165.38 (9)	C1—C2—C16—F2	−113.22 (13)
N2—C9—C10—C11	175.81 (8)	C3—C2—C16—F2	64.65 (14)
C14—C9—C10—C11	−4.35 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.86 (2)	2.05 (2)	2.8641 (13)	157 (1)
N2—H1N2···O3ii	0.86 (2)	2.13 (2)	2.9796 (12)	166 (1)
C5—H5···O1iii	0.95	2.46	3.3797 (14)	162
C14—H14B···O3ii	0.98	2.46	3.3571 (13)	153
C12—H12B···F3iv	0.99	2.47	3.2308 (15)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.86 (2)	2.05 (2)	2.8641 (13)	157 (1)
N2—H1N2⋯O3ii	0.86 (2)	2.13 (2)	2.9796 (12)	166 (1)
C5—H5⋯O1iii	0.95	2.46	3.3797 (14)	162
C14—H14B⋯O3ii	0.98	2.46	3.3571 (13)	153
C12—H12B⋯F3iv	0.99	2.47	3.2308 (15)	133

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