Ethyl 6-[4-(dimethyl-amino)phen-yl]-4-hydr-oxy-2-oxo-4-(trifluoro-methyl)-hexa-hydro-pyrimidine-5-carboxyl-ate.

The title compound, C(16)H(20)F(3)N(3)O(4), was prepared by reaction of 4-(dimethyl-amino)benzaldehyde, ethyl 4,4,4-trifluoro-3-oxo-butanoate and urea. In the title mol-ecule, the pyrimidine ring adopts a half-chair conformation and there is an intra-molecular hydrogen bond (O-H⋯O). The crystal structure is stabilized by two types inter-molecular hydrogen bonds (N-H⋯O and N-H⋯N).

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

C16H20F3N3O4

M = 375.35

Monoclinic,

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 ▶) T min = 0.971, T max = 0.983

11487 measured reflections

3081 independent reflections

2522 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 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

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); 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/MSC, 2005 ▶).

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013127/om2331Isup2.hkl

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

C16H20F3N3O4	F(000) = 784
Mr = 375.35	Dx = 1.431 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.319 (4) Å	Cell parameters from 6970 reflections
b = 7.923 (2) Å	θ = 1.5–27.9°
c = 16.530 (5) Å	µ = 0.12 mm−1
β = 92.720 (5)°	T = 116 K
V = 1742.3 (9) Å3	Prism, colorless
Z = 4	0.24 × 0.20 × 0.14 mm

Rigaku Saturn CCD area-detector diffractometer	3081 independent reflections
Radiation source: rotating anode	2522 reflections with I > 2σ(I)
multilayer	Rint = 0.030
Detector resolution: 14.63 pixels mm-1	θmax = 25.0°, θmin = 1.9°
ω and φ scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −9→9
Tmin = 0.971, Tmax = 0.983	l = −19→18
11487 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H 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 parameters	Δρmax = 0.17 e Å−3
3 restraints	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
F2	0.76872 (7)	0.70609 (12)	1.19210 (5)	0.0422 (3)
F3	0.87687 (7)	0.90599 (12)	1.18384 (5)	0.0419 (3)
F1	0.73912 (7)	0.91322 (12)	1.11033 (6)	0.0434 (3)
O1	0.93596 (8)	0.60732 (13)	1.11199 (6)	0.0292 (3)
O2	0.96896 (7)	0.91625 (12)	0.90354 (6)	0.0262 (3)
O3	0.78789 (9)	0.36331 (13)	1.10635 (6)	0.0385 (3)
O4	0.63911 (8)	0.47358 (14)	1.06174 (7)	0.0362 (3)
N1	0.90896 (9)	0.83310 (15)	1.02318 (7)	0.0231 (3)
N2	0.87955 (8)	0.67473 (14)	0.90588 (7)	0.0216 (3)
N3	0.57474 (8)	0.09436 (13)	0.76740 (7)	0.0214 (3)
C1	0.81144 (11)	0.81114 (19)	1.14029 (9)	0.0296 (4)
C2	0.86240 (10)	0.71282 (17)	1.07362 (8)	0.0220 (3)
C3	0.78493 (10)	0.60970 (16)	1.02222 (8)	0.0208 (3)
H3	0.7317	0.6850	1.0007	0.025*
C4	0.84102 (10)	0.53309 (17)	0.95139 (8)	0.0198 (3)
H4	0.8980	0.4669	0.9736	0.024*
C5	0.92246 (10)	0.81105 (16)	0.94208 (8)	0.0202 (3)
C6	0.73872 (11)	0.46902 (19)	1.06923 (9)	0.0275 (3)
C7	0.58484 (14)	0.3318 (2)	1.09539 (11)	0.0478 (5)
H7A	0.5231	0.3717	1.1176	0.057*
H7B	0.6256	0.2799	1.1388	0.057*
C8	0.56152 (16)	0.2067 (2)	1.03137 (11)	0.0555 (6)
H8A	0.5235	0.2597	0.9876	0.083*
H8B	0.5229	0.1164	1.0530	0.083*
H8C	0.6230	0.1625	1.0118	0.083*
C9	0.77484 (10)	0.41978 (16)	0.89851 (8)	0.0190 (3)
C10	0.79225 (10)	0.24776 (18)	0.89719 (8)	0.0213 (3)
H10	0.8479	0.2040	0.9262	0.026*
C11	0.72844 (10)	0.13904 (17)	0.85356 (8)	0.0219 (3)
H11	0.7419	0.0239	0.8535	0.026*
C12	0.64423 (10)	0.20114 (16)	0.80974 (8)	0.0195 (3)
C13	0.63014 (10)	0.37648 (17)	0.80716 (8)	0.0225 (3)
H13	0.5772	0.4215	0.7754	0.027*
C14	0.69393 (10)	0.48298 (17)	0.85123 (8)	0.0226 (3)
H14	0.6827	0.5988	0.8493	0.027*
C15	0.58978 (11)	−0.08702 (17)	0.77979 (8)	0.0254 (3)
H15A	0.6557	−0.1179	0.7640	0.038*
H15B	0.5403	−0.1483	0.7476	0.038*
H15C	0.5832	−0.1137	0.8359	0.038*
C16	0.46919 (10)	0.14840 (19)	0.77106 (9)	0.0301 (4)
H16A	0.4564	0.1830	0.8253	0.045*
H16B	0.4256	0.0561	0.7557	0.045*
H16C	0.4568	0.2412	0.7346	0.045*
H1	0.9050 (13)	0.5138 (16)	1.1199 (12)	0.054 (6)*
H1A	0.9442 (11)	0.9186 (15)	1.0458 (9)	0.032 (4)*
H2A	0.8942 (11)	0.6524 (19)	0.8542 (6)	0.032 (4)*

	U11	U22	U33	U12	U13	U23
F2	0.0505 (6)	0.0475 (6)	0.0302 (5)	−0.0197 (5)	0.0198 (4)	−0.0068 (4)
F3	0.0473 (6)	0.0502 (6)	0.0291 (5)	−0.0227 (5)	0.0115 (4)	−0.0174 (4)
F1	0.0429 (6)	0.0419 (6)	0.0464 (6)	0.0076 (4)	0.0123 (5)	−0.0114 (4)
O1	0.0280 (6)	0.0337 (6)	0.0254 (6)	−0.0022 (5)	−0.0052 (4)	0.0032 (5)
O2	0.0299 (6)	0.0269 (5)	0.0219 (5)	−0.0110 (4)	0.0029 (4)	0.0007 (4)
O3	0.0505 (8)	0.0332 (6)	0.0315 (6)	−0.0106 (5)	−0.0021 (5)	0.0088 (5)
O4	0.0305 (7)	0.0399 (7)	0.0393 (6)	−0.0165 (5)	0.0135 (5)	−0.0066 (5)
N1	0.0258 (7)	0.0239 (6)	0.0197 (6)	−0.0091 (5)	0.0022 (5)	−0.0034 (5)
N2	0.0252 (7)	0.0218 (6)	0.0180 (6)	−0.0073 (5)	0.0039 (5)	−0.0013 (5)
N3	0.0208 (6)	0.0217 (6)	0.0215 (6)	−0.0029 (5)	0.0001 (5)	−0.0020 (5)
C1	0.0296 (9)	0.0324 (8)	0.0274 (8)	−0.0096 (7)	0.0076 (6)	−0.0048 (7)
C2	0.0199 (7)	0.0257 (8)	0.0206 (7)	−0.0034 (6)	0.0013 (5)	0.0006 (6)
C3	0.0198 (7)	0.0216 (7)	0.0209 (7)	−0.0017 (5)	0.0010 (5)	0.0001 (6)
C4	0.0182 (7)	0.0199 (7)	0.0213 (7)	−0.0013 (5)	0.0014 (5)	0.0012 (6)
C5	0.0176 (7)	0.0215 (7)	0.0216 (7)	0.0001 (6)	0.0002 (5)	−0.0010 (6)
C6	0.0317 (9)	0.0284 (8)	0.0227 (7)	−0.0091 (7)	0.0055 (6)	−0.0051 (7)
C7	0.0497 (11)	0.0533 (11)	0.0422 (10)	−0.0325 (9)	0.0220 (8)	−0.0074 (9)
C8	0.0750 (15)	0.0473 (11)	0.0461 (11)	−0.0330 (10)	0.0243 (10)	−0.0123 (9)
C9	0.0187 (7)	0.0203 (7)	0.0181 (7)	−0.0021 (5)	0.0029 (5)	0.0003 (5)
C10	0.0188 (7)	0.0236 (7)	0.0214 (7)	0.0022 (6)	−0.0006 (5)	0.0007 (6)
C11	0.0247 (8)	0.0166 (7)	0.0244 (7)	0.0005 (6)	0.0021 (6)	−0.0005 (6)
C12	0.0188 (7)	0.0242 (7)	0.0159 (6)	−0.0029 (5)	0.0037 (5)	−0.0014 (5)
C13	0.0194 (7)	0.0250 (8)	0.0227 (7)	0.0014 (6)	−0.0028 (6)	0.0013 (6)
C14	0.0258 (8)	0.0170 (7)	0.0250 (7)	0.0014 (6)	0.0006 (6)	0.0016 (6)
C15	0.0295 (8)	0.0238 (8)	0.0229 (7)	−0.0064 (6)	0.0005 (6)	−0.0007 (6)
C16	0.0216 (8)	0.0375 (9)	0.0312 (8)	−0.0033 (6)	0.0012 (6)	−0.0079 (7)

F2—C1	1.3403 (17)	C4—H4	0.9800
F3—C1	1.3353 (17)	C7—C8	1.472 (2)
F1—C1	1.3348 (18)	C7—H7A	0.9700
O1—C2	1.4149 (17)	C7—H7B	0.9700
O1—H1	0.860 (9)	C8—H8A	0.9600
O2—C5	1.2335 (16)	C8—H8B	0.9600
O3—C6	1.2119 (19)	C8—H8C	0.9600
O4—C6	1.3271 (19)	C9—C10	1.3828 (19)
O4—C7	1.4601 (18)	C9—C14	1.3938 (19)
N1—C5	1.3722 (18)	C10—C11	1.3878 (19)
N1—C2	1.4273 (17)	C10—H10	0.9300
N1—H1A	0.896 (9)	C11—C12	1.3956 (19)
N2—C5	1.3486 (18)	C11—H11	0.9300
N2—C4	1.4578 (17)	C12—C13	1.4021 (19)
N2—H2A	0.902 (9)	C13—C14	1.3805 (19)
N3—C12	1.4145 (17)	C13—H13	0.9300
N3—C15	1.4640 (17)	C14—H14	0.9300
N3—C16	1.4735 (18)	C15—H15A	0.9600
C1—C2	1.534 (2)	C15—H15B	0.9600
C2—C3	1.5397 (19)	C15—H15C	0.9600
C3—C6	1.5067 (19)	C16—H16A	0.9600
C3—C4	1.5429 (18)	C16—H16B	0.9600
C3—H3	0.9800	C16—H16C	0.9600
C4—C9	1.5079 (19)
C2—O1—H1	104.5 (13)	O4—C7—H7A	109.8
C6—O4—C7	117.02 (14)	C8—C7—H7A	109.8
C5—N1—C2	124.51 (12)	O4—C7—H7B	109.8
C5—N1—H1A	114.4 (11)	C8—C7—H7B	109.8
C2—N1—H1A	119.6 (10)	H7A—C7—H7B	108.2
C5—N2—C4	122.66 (11)	C7—C8—H8A	109.5
C5—N2—H2A	118.1 (10)	C7—C8—H8B	109.5
C4—N2—H2A	115.7 (10)	H8A—C8—H8B	109.5
C12—N3—C15	115.84 (11)	C7—C8—H8C	109.5
C12—N3—C16	114.14 (11)	H8A—C8—H8C	109.5
C15—N3—C16	113.82 (11)	H8B—C8—H8C	109.5
F1—C1—F3	107.46 (12)	C10—C9—C14	118.10 (12)
F1—C1—F2	107.01 (12)	C10—C9—C4	120.13 (12)
F3—C1—F2	106.92 (12)	C14—C9—C4	121.75 (12)
F1—C1—C2	112.17 (12)	C9—C10—C11	121.39 (12)
F3—C1—C2	111.93 (12)	C9—C10—H10	119.3
F2—C1—C2	111.06 (12)	C11—C10—H10	119.3
O1—C2—N1	110.21 (11)	C10—C11—C12	120.54 (13)
O1—C2—C1	107.38 (11)	C10—C11—H11	119.7
N1—C2—C1	107.45 (12)	C12—C11—H11	119.7
O1—C2—C3	111.44 (11)	C11—C12—C13	117.92 (12)
N1—C2—C3	109.29 (11)	C11—C12—N3	122.47 (12)
C1—C2—C3	110.99 (11)	C13—C12—N3	119.60 (12)
C6—C3—C2	112.79 (11)	C14—C13—C12	120.75 (12)
C6—C3—C4	108.95 (11)	C14—C13—H13	119.6
C2—C3—C4	106.95 (11)	C12—C13—H13	119.6
C6—C3—H3	109.4	C13—C14—C9	121.09 (12)
C2—C3—H3	109.4	C13—C14—H14	119.5
C4—C3—H3	109.4	C9—C14—H14	119.5
N2—C4—C9	111.69 (11)	N3—C15—H15A	109.5
N2—C4—C3	106.48 (11)	N3—C15—H15B	109.5
C9—C4—C3	112.54 (11)	H15A—C15—H15B	109.5
N2—C4—H4	108.7	N3—C15—H15C	109.5
C9—C4—H4	108.7	H15A—C15—H15C	109.5
C3—C4—H4	108.7	H15B—C15—H15C	109.5
O2—C5—N2	121.65 (12)	N3—C16—H16A	109.5
O2—C5—N1	120.72 (12)	N3—C16—H16B	109.5
N2—C5—N1	117.58 (12)	H16A—C16—H16B	109.5
O3—C6—O4	125.44 (14)	N3—C16—H16C	109.5
O3—C6—C3	123.25 (14)	H16A—C16—H16C	109.5
O4—C6—C3	111.27 (13)	H16B—C16—H16C	109.5
O4—C7—C8	109.59 (14)
C5—N1—C2—O1	93.48 (15)	C2—N1—C5—N2	7.3 (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—C3	172.21 (12)
F1—C1—C2—O1	−179.00 (11)	C2—C3—C6—O3	−53.65 (18)
F3—C1—C2—O1	60.12 (15)	C4—C3—C6—O3	64.94 (17)
F2—C1—C2—O1	−59.30 (14)	C2—C3—C6—O4	128.71 (12)
F1—C1—C2—N1	62.46 (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—C10	128.63 (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—C3	62.72 (15)	C3—C4—C9—C14	67.00 (15)
O1—C2—C3—C6	52.81 (15)	C14—C9—C10—C11	−3.27 (19)
N1—C2—C3—C6	174.86 (11)	C4—C9—C10—C11	175.43 (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—C13	4.00 (19)
N1—C2—C3—C4	55.11 (14)	C10—C11—C12—N3	−177.11 (11)
C1—C2—C3—C4	173.44 (11)	C15—N3—C12—C11	6.82 (18)
C5—N2—C4—C9	165.79 (12)	C16—N3—C12—C11	141.96 (13)
C5—N2—C4—C3	42.56 (16)	C15—N3—C12—C13	−174.31 (12)
C6—C3—C4—N2	177.15 (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—C9	54.46 (15)	N3—C12—C13—C14	176.70 (12)
C2—C3—C4—C9	176.66 (11)	C12—C13—C14—C9	1.0 (2)
C4—N2—C5—O2	168.05 (12)	C10—C9—C14—C13	2.89 (19)
C4—N2—C5—N1	−14.73 (19)	C4—C9—C14—C13	−175.79 (12)
C2—N1—C5—O2	−175.47 (12)

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)

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) ; (ii) .