5-Benzoyl-4-(4-fluoro-phen-yl)-3,4-dihydro-pyrimidin-2(1H)-one.

In the title mol-ecule, C(17)H(13)FN(2)O(2), the 3,4-dihydro-pyrimidine ring adopts a flattened sofa conformation with the flap atom (which bears the fluoro-phenyl substituent) deviating from the plane defined by the remaining five ring atoms by 0.281 (2) Å. This plane forms dihedral angles of 85.98 (6) and 60.63 (6)° with the 4-fluoro-phenyl and benzoyl-phenyl rings, respectively. The dihedral angle between the 4-fluoro-phenyl group and the benzene ring is 71.78 (6)°. In the crystal, N-H⋯O hydrogen bonds link mol-ecules into inversion dimers that are further connected by another N-H⋯O inter-action into a two-dimensional supra-molecular structure parallel to (101).

Related literature

For general background to and pharmaceutical applications of pyrimidino­nes, see: Ghorab et al. (2000 ▶); Shivarama Holla et al. (2004 ▶); Stefani et al. (2006 ▶). For related structures, see: Fun et al. (2009 ▶); Chitra et al. (2009 ▶). For asymmetry parameters, see: Duax & Norton (1975 ▶).

Experimental

Crystal data

C17H13FN2O2

M = 296.29

Monoclinic,

a = 12.7911 (5) Å

b = 8.1862 (3) Å

c = 13.7325 (5) Å

β = 98.850 (4)°

V = 1420.82 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.777, T max = 1.000

27552 measured reflections

2786 independent reflections

1836 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.131

S = 1.04

2786 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812052105/gk2549sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812052105/gk2549Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812052105/gk2549Isup3.cml

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

C17H13FN2O2	F(000) = 616
Mr = 296.29	Dx = 1.385 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9924 reflections
a = 12.7911 (5) Å	θ = 3.4–29.0°
b = 8.1862 (3) Å	µ = 0.10 mm−1
c = 13.7325 (5) Å	T = 293 K
β = 98.850 (4)°	Block, colourless
V = 1420.82 (9) Å3	0.3 × 0.2 × 0.2 mm
Z = 4

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2786 independent reflections
Radiation source: fine-focus sealed tube	1836 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.4°
ω scans	h = −15→15
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −10→10
Tmin = 0.777, Tmax = 1.000	l = −16→16
27552 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0593P)2 + 0.117P] where P = (Fo2 + 2Fc2)/3
2786 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
O1	0.39760 (11)	0.04963 (17)	0.86034 (11)	0.0532 (4)
O2	0.37270 (12)	0.57074 (18)	0.52393 (11)	0.0584 (5)
F1	0.33786 (14)	0.71433 (18)	1.06679 (11)	0.0932 (5)
N1	0.48454 (13)	0.3865 (2)	0.60718 (13)	0.0497 (5)
H1	0.5352	0.4189	0.5774	0.060*
C2	0.38882 (16)	0.4658 (2)	0.58943 (15)	0.0428 (5)
N3	0.31734 (13)	0.42049 (19)	0.64458 (12)	0.0436 (4)
H3	0.2539	0.4556	0.6267	0.052*
C4	0.33496 (15)	0.3167 (2)	0.73290 (14)	0.0386 (5)
H4	0.2746	0.2422	0.7299	0.046*
C5	0.43279 (15)	0.2146 (2)	0.72997 (14)	0.0383 (5)
C6	0.50143 (16)	0.2583 (2)	0.67049 (15)	0.0429 (5)
H6	0.5635	0.1983	0.6725	0.051*
C7	0.45121 (15)	0.0738 (2)	0.79487 (15)	0.0401 (5)
C8	0.53687 (15)	−0.0452 (2)	0.78012 (15)	0.0406 (5)
C9	0.54036 (17)	−0.1174 (2)	0.68944 (16)	0.0506 (6)
H9	0.4915	−0.0867	0.6352	0.061*
C10	0.61561 (19)	−0.2345 (3)	0.67854 (19)	0.0603 (6)
H10	0.6164	−0.2836	0.6176	0.072*
C11	0.6889 (2)	−0.2778 (3)	0.7576 (2)	0.0674 (7)
H11	0.7398	−0.3562	0.7503	0.081*
C12	0.68740 (19)	−0.2060 (3)	0.8473 (2)	0.0642 (7)
H12	0.7382	−0.2348	0.9005	0.077*
C13	0.61117 (18)	−0.0912 (2)	0.85984 (17)	0.0502 (6)
H13	0.6098	−0.0450	0.9215	0.060*
C14	0.33820 (15)	0.4208 (2)	0.82489 (14)	0.0374 (5)
C15	0.41687 (18)	0.5364 (3)	0.85035 (16)	0.0507 (6)
H15	0.4704	0.5474	0.8120	0.061*
C16	0.4170 (2)	0.6356 (3)	0.93181 (17)	0.0598 (6)
H16	0.4698	0.7131	0.9485	0.072*
C17	0.3384 (2)	0.6174 (3)	0.98687 (17)	0.0578 (6)
C18	0.2588 (2)	0.5067 (3)	0.96424 (17)	0.0582 (6)
H18	0.2049	0.4986	1.0024	0.070*
C19	0.26005 (17)	0.4065 (2)	0.88326 (16)	0.0480 (5)
H19	0.2073	0.3283	0.8680	0.058*

	U11	U22	U33	U12	U13	U23
O1	0.0473 (9)	0.0574 (9)	0.0592 (9)	0.0000 (7)	0.0219 (8)	0.0136 (7)
O2	0.0593 (10)	0.0675 (10)	0.0529 (9)	0.0202 (8)	0.0223 (8)	0.0227 (8)
F1	0.1272 (14)	0.0846 (10)	0.0730 (10)	−0.0053 (10)	0.0323 (10)	−0.0299 (8)
N1	0.0388 (10)	0.0546 (10)	0.0600 (11)	0.0094 (8)	0.0215 (9)	0.0197 (9)
C2	0.0419 (12)	0.0473 (12)	0.0407 (11)	0.0065 (9)	0.0113 (9)	0.0021 (10)
N3	0.0329 (9)	0.0572 (10)	0.0415 (9)	0.0100 (8)	0.0084 (8)	0.0092 (8)
C4	0.0318 (11)	0.0403 (10)	0.0454 (11)	0.0005 (8)	0.0114 (9)	0.0059 (9)
C5	0.0333 (11)	0.0390 (10)	0.0434 (11)	0.0007 (8)	0.0085 (9)	0.0023 (9)
C6	0.0356 (11)	0.0436 (11)	0.0510 (12)	0.0056 (9)	0.0113 (10)	0.0075 (9)
C7	0.0352 (11)	0.0398 (10)	0.0457 (12)	−0.0046 (9)	0.0076 (9)	0.0013 (9)
C8	0.0356 (11)	0.0356 (10)	0.0518 (12)	−0.0036 (9)	0.0104 (9)	0.0043 (9)
C9	0.0443 (13)	0.0534 (13)	0.0539 (14)	−0.0003 (10)	0.0068 (11)	−0.0008 (10)
C10	0.0544 (15)	0.0568 (14)	0.0713 (17)	0.0000 (12)	0.0145 (13)	−0.0135 (12)
C11	0.0524 (16)	0.0509 (14)	0.099 (2)	0.0110 (11)	0.0109 (15)	−0.0053 (14)
C12	0.0471 (15)	0.0578 (14)	0.0825 (18)	0.0111 (12)	−0.0063 (13)	0.0104 (13)
C13	0.0499 (14)	0.0440 (12)	0.0548 (13)	−0.0032 (10)	0.0022 (11)	0.0048 (10)
C14	0.0361 (11)	0.0353 (10)	0.0418 (11)	0.0028 (9)	0.0089 (9)	0.0067 (8)
C15	0.0477 (14)	0.0549 (13)	0.0522 (13)	−0.0060 (10)	0.0160 (11)	0.0003 (10)
C16	0.0679 (17)	0.0523 (13)	0.0589 (14)	−0.0110 (12)	0.0091 (13)	−0.0048 (12)
C17	0.0790 (18)	0.0484 (13)	0.0480 (13)	0.0049 (12)	0.0159 (12)	−0.0062 (11)
C18	0.0688 (17)	0.0569 (14)	0.0566 (14)	0.0052 (12)	0.0346 (13)	0.0029 (12)
C19	0.0468 (13)	0.0436 (12)	0.0571 (13)	−0.0019 (9)	0.0190 (11)	0.0030 (10)

O1—C7	1.228 (2)	C9—H9	0.9300
O2—C2	1.238 (2)	C10—C11	1.367 (3)
F1—C17	1.355 (2)	C10—H10	0.9300
N1—C6	1.359 (2)	C11—C12	1.369 (3)
N1—C2	1.374 (3)	C11—H11	0.9300
N1—H1	0.8600	C12—C13	1.384 (3)
C2—N3	1.327 (2)	C12—H12	0.9300
N3—C4	1.470 (2)	C13—H13	0.9300
N3—H3	0.8600	C14—C19	1.379 (3)
C4—C5	1.511 (3)	C14—C15	1.387 (3)
C4—C14	1.519 (3)	C15—C16	1.382 (3)
C4—H4	0.9800	C15—H15	0.9300
C5—C6	1.337 (3)	C16—C17	1.356 (3)
C5—C7	1.454 (3)	C16—H16	0.9300
C6—H6	0.9300	C17—C18	1.362 (3)
C7—C8	1.503 (3)	C18—C19	1.384 (3)
C8—C9	1.385 (3)	C18—H18	0.9300
C8—C13	1.387 (3)	C19—H19	0.9300
C9—C10	1.383 (3)
C6—N1—C2	121.89 (17)	C11—C10—C9	119.9 (2)
C6—N1—H1	119.1	C11—C10—H10	120.1
C2—N1—H1	119.1	C9—C10—H10	120.1
O2—C2—N3	123.82 (18)	C10—C11—C12	120.0 (2)
O2—C2—N1	120.08 (18)	C10—C11—H11	120.0
N3—C2—N1	116.09 (17)	C12—C11—H11	120.0
C2—N3—C4	126.95 (16)	C11—C12—C13	120.7 (2)
C2—N3—H3	116.5	C11—C12—H12	119.6
C4—N3—H3	116.5	C13—C12—H12	119.6
N3—C4—C5	108.69 (15)	C12—C13—C8	119.8 (2)
N3—C4—C14	110.09 (14)	C12—C13—H13	120.1
C5—C4—C14	114.58 (16)	C8—C13—H13	120.1
N3—C4—H4	107.7	C19—C14—C15	118.29 (19)
C5—C4—H4	107.7	C19—C14—C4	120.43 (18)
C14—C4—H4	107.7	C15—C14—C4	121.23 (17)
C6—C5—C7	121.81 (17)	C16—C15—C14	121.0 (2)
C6—C5—C4	119.51 (17)	C16—C15—H15	119.5
C7—C5—C4	118.64 (16)	C14—C15—H15	119.5
C5—C6—N1	122.90 (18)	C17—C16—C15	118.6 (2)
C5—C6—H6	118.6	C17—C16—H16	120.7
N1—C6—H6	118.6	C15—C16—H16	120.7
O1—C7—C5	121.36 (17)	F1—C17—C16	118.9 (2)
O1—C7—C8	119.69 (17)	F1—C17—C18	118.5 (2)
C5—C7—C8	118.95 (17)	C16—C17—C18	122.5 (2)
C9—C8—C13	118.75 (19)	C17—C18—C19	118.5 (2)
C9—C8—C7	121.50 (19)	C17—C18—H18	120.7
C13—C8—C7	119.67 (19)	C19—C18—H18	120.7
C10—C9—C8	120.8 (2)	C14—C19—C18	121.0 (2)
C10—C9—H9	119.6	C14—C19—H19	119.5
C8—C9—H9	119.6	C18—C19—H19	119.5
C6—N1—C2—O2	−172.51 (19)	C7—C8—C9—C10	−175.79 (18)
C6—N1—C2—N3	6.3 (3)	C8—C9—C10—C11	−1.2 (3)
O2—C2—N3—C4	−169.86 (18)	C9—C10—C11—C12	0.3 (4)
N1—C2—N3—C4	11.4 (3)	C10—C11—C12—C13	1.1 (4)
C2—N3—C4—C5	−22.5 (3)	C11—C12—C13—C8	−1.5 (3)
C2—N3—C4—C14	103.8 (2)	C9—C8—C13—C12	0.6 (3)
N3—C4—C5—C6	17.7 (3)	C7—C8—C13—C12	177.22 (19)
C14—C4—C5—C6	−105.9 (2)	N3—C4—C14—C19	113.42 (19)
N3—C4—C5—C7	−164.33 (16)	C5—C4—C14—C19	−123.7 (2)
C14—C4—C5—C7	72.1 (2)	N3—C4—C14—C15	−64.1 (2)
C7—C5—C6—N1	178.06 (18)	C5—C4—C14—C15	58.8 (2)
C4—C5—C6—N1	−4.0 (3)	C19—C14—C15—C16	−0.3 (3)
C2—N1—C6—C5	−9.6 (3)	C4—C14—C15—C16	177.24 (19)
C6—C5—C7—O1	167.94 (19)	C14—C15—C16—C17	0.1 (3)
C4—C5—C7—O1	−10.0 (3)	C15—C16—C17—F1	−179.9 (2)
C6—C5—C7—C8	−12.9 (3)	C15—C16—C17—C18	−0.8 (4)
C4—C5—C7—C8	169.22 (17)	F1—C17—C18—C19	−179.3 (2)
O1—C7—C8—C9	125.5 (2)	C16—C17—C18—C19	1.6 (4)
C5—C7—C8—C9	−53.7 (2)	C15—C14—C19—C18	1.1 (3)
O1—C7—C8—C13	−51.0 (3)	C4—C14—C19—C18	−176.45 (18)
C5—C7—C8—C13	129.8 (2)	C17—C18—C19—C14	−1.7 (3)
C13—C8—C9—C10	0.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	1.96	2.777 (2)	159
N3—H3···O1ii	0.86	2.12	2.937 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	1.96	2.777 (2)	159
N3—H3⋯O1ii	0.86	2.12	2.937 (2)	159

Symmetry codes: (i) ; (ii) .