3-(4-Bromo-phen-yl)-3-(4-hydr-oxy-6-oxo-1,6-dihydro-pyrimidin-5-yl)-N-[(S)-1-phenyl-ethyl]propanamide.

In the mol-ecule of the title compound, C(21)H(20)BrN(3)O(3), the pyrimidine ring is oriented at dihedral angles of 80.87 (3) and 15.99 (3)°, respectively, to the pyrimidine and bromo-phenyl rings. The dihedral angle between the two benzene rings is 88.37 (3)°. In the crystal structure, inter-molecular N-H⋯O and O-H⋯N hydrogen bonds link the mol-ecules. A π-π contact between pyrimidine and phenyl rings [centroid-centroid distance = 3.776 (3) Å] may further stabilize the structure. The methine H and the methyl C and H atoms are disordered over two positions and were refined with occupancies of 0.522 (13) and 0.478 (13).

Related literature

For general background, see: Johar et al. (2005 ▶); Janeba et al. (2005 ▶); Soloducho et al. (2003 ▶); Mathews & Asokan (2007 ▶); Lagoja (2005 ▶); Michael (2005 ▶); Erian (1993 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C21H20BrN3O3

M = 442.31

Triclinic,

a = 7.147 (1) Å

b = 12.5010 (14) Å

c = 13.0940 (16) Å

α = 118.506 (2)°

β = 99.047 (1)°

γ = 93.074 (1)°

V = 1004.0 (2) Å3

Z = 2

Mo Kα radiation

μ = 2.07 mm−1

T = 298 (2) K

0.20 × 0.18 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.682, T max = 0.719

5285 measured reflections

3498 independent reflections

1810 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.162

S = 1.06

3498 reflections

265 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.43 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003821/hk2614sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003821/hk2614Isup2.hkl

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

C21H20BrN3O3	Z = 2
Mr = 442.31	F(000) = 452
Triclinic, P1	Dx = 1.463 Mg m−3
Hall symbol: -P 1	Melting point = 551–553 K
a = 7.147 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.5010 (14) Å	Cell parameters from 1260 reflections
c = 13.0940 (16) Å	θ = 3.1–25.2°
α = 118.506 (2)°	µ = 2.07 mm−1
β = 99.047 (1)°	T = 298 K
γ = 93.074 (1)°	Block, colorless
V = 1004.0 (2) Å3	0.20 × 0.18 × 0.17 mm

Bruker SMART CCD area-detector diffractometer	3498 independent reflections
Radiation source: fine-focus sealed tube	1810 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −8→8
Tmin = 0.682, Tmax = 0.719	k = −14→14
5285 measured reflections	l = −15→12

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0673P)2] where P = (Fo2 + 2Fc2)/3
3498 reflections	(Δ/σ)max = 0.001
265 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.43 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	Occ. (<1)
Br1	0.19659 (12)	−0.19766 (6)	0.27241 (8)	0.1005 (4)
O1	0.5807 (5)	0.4123 (3)	0.5600 (3)	0.0571 (10)
O2	0.3046 (5)	0.4229 (4)	0.8648 (3)	0.0636 (11)
H2	0.3406	0.4455	0.9356	0.095*
O3	0.0791 (5)	0.5971 (3)	0.7386 (3)	0.0556 (10)
N1	0.7505 (6)	0.4888 (4)	0.7474 (4)	0.0428 (11)
H1	0.8512	0.5063	0.7267	0.051*
N2	0.6202 (6)	0.4935 (4)	0.9004 (4)	0.0478 (11)
N3	0.3055 (6)	0.6437 (4)	0.6606 (4)	0.0475 (11)
H3	0.3644	0.6160	0.6026	0.057*
C1	0.5815 (7)	0.4342 (4)	0.6618 (5)	0.0408 (12)
C2	0.4203 (7)	0.4109 (4)	0.7041 (4)	0.0394 (12)
C3	0.4498 (7)	0.4424 (5)	0.8225 (4)	0.0417 (13)
C4	0.7634 (7)	0.5149 (5)	0.8586 (5)	0.0450 (13)
H4	0.8816	0.5508	0.9104	0.054*
C5	0.1767 (7)	0.5650 (5)	0.6613 (4)	0.0420 (13)
C6	0.1587 (8)	0.4333 (4)	0.5658 (4)	0.0445 (13)
H6A	0.2353	0.4275	0.5088	0.053*
H6B	0.0262	0.4026	0.5241	0.053*
C7	0.2281 (7)	0.3561 (4)	0.6225 (4)	0.0429 (13)
H7	0.1378	0.3585	0.6725	0.051*
C8	0.2223 (7)	0.2209 (5)	0.5337 (5)	0.0457 (13)
C9	0.2544 (10)	0.1396 (5)	0.5734 (6)	0.0734 (19)
H9	0.2786	0.1682	0.6548	0.088*
C10	0.2523 (11)	0.0158 (6)	0.4969 (7)	0.084 (2)
H10	0.2783	−0.0369	0.5271	0.101*
C11	0.2120 (9)	−0.0288 (5)	0.3769 (6)	0.0642 (17)
C12	0.1737 (11)	0.0496 (6)	0.3352 (6)	0.088 (2)
H12	0.1444	0.0200	0.2537	0.105*
C13	0.1777 (11)	0.1740 (5)	0.4129 (5)	0.079 (2)
H13	0.1496	0.2263	0.3826	0.094*
C14	0.3576 (10)	0.7744 (6)	0.7498 (6)	0.0682 (17)
H14	0.2380	0.7946	0.7776	0.082*	0.522 (13)
H14'	0.4428	0.8049	0.7146	0.082*	0.478 (13)
C15	0.4908 (10)	0.7923 (5)	0.8600 (6)	0.0644 (17)
C16	0.4207 (11)	0.7902 (7)	0.9509 (7)	0.085 (2)
H16	0.2890	0.7782	0.9449	0.102*
C17	0.5439 (14)	0.8058 (7)	1.0516 (7)	0.099 (2)
H17	0.4949	0.8039	1.1125	0.119*
C18	0.7363 (16)	0.8239 (7)	1.0612 (8)	0.105 (3)
H18	0.8182	0.8344	1.1289	0.126*
C19	0.8110 (12)	0.8270 (7)	0.9733 (10)	0.108 (3)
H19	0.9430	0.8394	0.9804	0.129*
C20	0.6863 (11)	0.8114 (7)	0.8724 (8)	0.090 (2)
H20	0.7365	0.8138	0.8121	0.108*
C21	0.3839 (18)	0.8563 (10)	0.6965 (11)	0.072 (5)	0.522 (13)
H21A	0.2689	0.8443	0.6410	0.108*	0.522 (13)
H21B	0.4888	0.8360	0.6562	0.108*	0.522 (13)
H21C	0.4108	0.9408	0.7585	0.108*	0.522 (13)
C21'	0.211 (2)	0.8496 (13)	0.7670 (15)	0.096 (7)	0.478 (13)
H21D	0.1534	0.8433	0.6926	0.144*	0.478 (13)
H21E	0.2647	0.9336	0.8230	0.144*	0.478 (13)
H21F	0.1152	0.8226	0.7970	0.144*	0.478 (13)

	U11	U22	U33	U12	U13	U23
Br1	0.0949 (6)	0.0471 (4)	0.1247 (8)	0.0142 (4)	0.0106 (5)	0.0183 (4)
O1	0.064 (3)	0.080 (3)	0.037 (2)	0.007 (2)	0.0134 (19)	0.035 (2)
O2	0.045 (2)	0.106 (3)	0.037 (2)	−0.023 (2)	−0.0018 (18)	0.040 (2)
O3	0.046 (2)	0.062 (2)	0.052 (2)	−0.0011 (19)	0.018 (2)	0.020 (2)
N1	0.036 (3)	0.052 (3)	0.040 (3)	0.003 (2)	0.008 (2)	0.023 (2)
N2	0.045 (3)	0.060 (3)	0.032 (3)	−0.008 (2)	−0.001 (2)	0.021 (2)
N3	0.051 (3)	0.051 (3)	0.039 (3)	0.001 (2)	0.014 (2)	0.020 (2)
C1	0.045 (3)	0.045 (3)	0.038 (3)	0.006 (3)	0.014 (3)	0.023 (3)
C2	0.045 (3)	0.040 (3)	0.034 (3)	−0.001 (2)	0.004 (2)	0.020 (3)
C3	0.039 (3)	0.052 (3)	0.035 (3)	−0.004 (3)	0.004 (3)	0.024 (3)
C4	0.036 (3)	0.058 (3)	0.039 (4)	0.003 (3)	0.002 (3)	0.025 (3)
C5	0.039 (3)	0.049 (3)	0.038 (3)	0.006 (3)	0.006 (3)	0.023 (3)
C6	0.050 (3)	0.047 (3)	0.034 (3)	0.002 (3)	0.001 (2)	0.020 (3)
C7	0.045 (3)	0.043 (3)	0.036 (3)	−0.001 (3)	0.005 (3)	0.018 (3)
C8	0.047 (3)	0.047 (3)	0.041 (3)	−0.002 (3)	0.003 (3)	0.022 (3)
C9	0.109 (6)	0.056 (4)	0.054 (4)	0.007 (4)	0.000 (4)	0.031 (4)
C10	0.110 (6)	0.055 (4)	0.081 (5)	0.012 (4)	0.002 (4)	0.034 (4)
C11	0.062 (4)	0.048 (3)	0.068 (5)	0.004 (3)	0.007 (3)	0.020 (4)
C12	0.130 (7)	0.057 (4)	0.059 (5)	0.007 (4)	0.000 (4)	0.020 (4)
C13	0.131 (6)	0.048 (4)	0.044 (4)	0.008 (4)	−0.006 (4)	0.020 (3)
C14	0.079 (5)	0.057 (4)	0.063 (4)	−0.005 (4)	0.005 (4)	0.030 (4)
C15	0.067 (5)	0.049 (3)	0.060 (4)	−0.004 (3)	0.007 (4)	0.017 (3)
C16	0.076 (5)	0.099 (6)	0.063 (5)	−0.004 (4)	0.009 (4)	0.029 (4)
C17	0.105 (7)	0.100 (6)	0.066 (6)	−0.007 (5)	0.000 (5)	0.028 (5)
C18	0.107 (8)	0.081 (5)	0.082 (7)	0.006 (5)	−0.016 (6)	0.016 (5)
C19	0.070 (6)	0.098 (6)	0.110 (8)	0.006 (5)	−0.005 (6)	0.024 (6)
C20	0.070 (5)	0.092 (5)	0.091 (6)	0.003 (4)	0.018 (5)	0.032 (5)
C21	0.071 (9)	0.059 (7)	0.088 (10)	0.001 (6)	0.007 (7)	0.042 (7)
C21'	0.094 (13)	0.066 (9)	0.104 (13)	0.014 (9)	−0.007 (10)	0.031 (9)

Br1—C11	1.874 (6)	C10—H10	0.9300
O1—C1	1.225 (5)	C11—C12	1.352 (8)
O2—C3	1.314 (5)	C12—C13	1.389 (8)
O2—H2	0.8200	C12—H12	0.9300
O3—C5	1.239 (5)	C13—H13	0.9300
N1—C4	1.318 (6)	C14—C21'	1.418 (15)
N1—C1	1.391 (6)	C14—C21	1.507 (12)
N1—H1	0.8600	C14—C15	1.508 (9)
N2—C4	1.305 (6)	C14—H14	0.9800
N2—C3	1.355 (6)	C14—H14'	0.9800
N3—C5	1.315 (6)	C15—C16	1.373 (9)
N3—C14	1.467 (7)	C15—C20	1.375 (9)
N3—H3	0.8600	C16—C17	1.387 (10)
C1—C2	1.428 (7)	C16—H16	0.9300
C2—C3	1.381 (6)	C17—C18	1.358 (11)
C2—C7	1.495 (7)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.357 (11)
C5—C6	1.500 (7)	C18—H18	0.9300
C6—C7	1.534 (6)	C19—C20	1.394 (11)
C6—H6A	0.9700	C19—H19	0.9300
C6—H6B	0.9700	C20—H20	0.9300
C7—C8	1.520 (7)	C21—H14'	0.8878
C7—H7	0.9800	C21—H21A	0.9600
C8—C9	1.360 (7)	C21—H21B	0.9600
C8—C13	1.372 (8)	C21—H21C	0.9600
C9—C10	1.382 (8)	C21'—H21D	0.9600
C9—H9	0.9300	C21'—H21E	0.9600
C10—C11	1.366 (9)	C21'—H21F	0.9600
C3—O2—H2	109.5	C11—C12—C13	120.6 (6)
C4—N1—C1	123.0 (4)	C11—C12—H12	119.7
C4—N1—H1	118.5	C13—C12—H12	119.7
C1—N1—H1	118.5	C8—C13—C12	121.2 (6)
C4—N2—C3	116.3 (4)	C8—C13—H13	119.4
C5—N3—C14	125.9 (5)	C12—C13—H13	119.4
C5—N3—H3	117.1	C21'—C14—N3	117.5 (8)
C14—N3—H3	117.1	C21'—C14—C21	69.8 (8)
O1—C1—N1	119.3 (4)	N3—C14—C21	113.2 (7)
O1—C1—C2	125.8 (5)	C21'—C14—C15	116.8 (9)
N1—C1—C2	114.9 (5)	N3—C14—C15	111.5 (5)
C3—C2—C1	117.2 (5)	C21—C14—C15	122.5 (7)
C3—C2—C7	122.2 (4)	N3—C14—H14	102.1
C1—C2—C7	120.5 (4)	C21—C14—H14	102.1
O2—C3—N2	116.5 (4)	C15—C14—H14	102.1
O2—C3—C2	119.0 (5)	C21'—C14—H14'	103.5
N2—C3—C2	124.6 (4)	N3—C14—H14'	102.5
N2—C4—N1	124.0 (5)	C15—C14—H14'	102.1
N2—C4—H4	118.0	C16—C15—C20	118.0 (7)
N1—C4—H4	118.0	C16—C15—C14	121.0 (6)
O3—C5—N3	121.8 (5)	C20—C15—C14	120.9 (7)
O3—C5—C6	121.8 (5)	C15—C16—C17	120.8 (7)
N3—C5—C6	116.3 (4)	C15—C16—H16	119.6
C5—C6—C7	109.1 (4)	C17—C16—H16	119.6
C5—C6—H6A	109.9	C18—C17—C16	119.9 (8)
C7—C6—H6A	109.9	C18—C17—H17	120.0
C5—C6—H6B	109.9	C16—C17—H17	120.0
C7—C6—H6B	109.9	C19—C18—C17	121.0 (8)
H6A—C6—H6B	108.3	C19—C18—H18	119.5
C2—C7—C8	111.5 (4)	C17—C18—H18	119.5
C2—C7—C6	112.3 (4)	C18—C19—C20	118.8 (8)
C8—C7—C6	114.0 (4)	C18—C19—H19	120.6
C2—C7—H7	106.1	C20—C19—H19	120.6
C8—C7—H7	106.1	C15—C20—C19	121.5 (8)
C6—C7—H7	106.1	C15—C20—H20	119.2
C9—C8—C13	117.0 (5)	C19—C20—H20	119.2
C9—C8—C7	119.6 (5)	C14—C21—H21A	109.5
C13—C8—C7	123.3 (5)	C14—C21—H21B	109.5
C8—C9—C10	122.2 (6)	C14—C21—H21C	109.5
C8—C9—H9	118.9	H14'—C21—H21C	114.6
C10—C9—H9	118.9	C14—C21'—H21D	109.5
C11—C10—C9	119.9 (6)	C14—C21'—H21E	109.5
C11—C10—H10	120.1	H21D—C21'—H21E	109.5
C9—C10—H10	120.1	C14—C21'—H21F	109.5
C12—C11—C10	118.9 (6)	H21D—C21'—H21F	109.5
C12—C11—Br1	120.8 (5)	H21E—C21'—H21F	109.5
C10—C11—Br1	120.2 (5)
C4—N1—C1—O1	−179.8 (5)	C13—C8—C9—C10	3.2 (10)
C4—N1—C1—C2	1.4 (7)	C7—C8—C9—C10	−179.5 (6)
O1—C1—C2—C3	−179.8 (5)	C8—C9—C10—C11	−1.8 (11)
N1—C1—C2—C3	−1.0 (6)	C9—C10—C11—C12	−0.4 (11)
O1—C1—C2—C7	−0.6 (8)	C9—C10—C11—Br1	−176.9 (5)
N1—C1—C2—C7	178.1 (4)	C10—C11—C12—C13	0.9 (11)
C4—N2—C3—O2	−178.8 (5)	Br1—C11—C12—C13	177.4 (6)
C4—N2—C3—C2	1.0 (8)	C9—C8—C13—C12	−2.6 (10)
C1—C2—C3—O2	179.6 (4)	C7—C8—C13—C12	−179.8 (6)
C7—C2—C3—O2	0.5 (7)	C11—C12—C13—C8	0.7 (12)
C1—C2—C3—N2	−0.1 (8)	C5—N3—C14—C21'	−59.8 (11)
C7—C2—C3—N2	−179.3 (5)	C5—N3—C14—C21	−138.3 (7)
C3—N2—C4—N1	−0.7 (8)	C5—N3—C14—C15	78.9 (7)
C1—N1—C4—N2	−0.5 (8)	C21'—C14—C15—C16	51.4 (11)
C14—N3—C5—O3	2.8 (8)	N3—C14—C15—C16	−87.7 (8)
C14—N3—C5—C6	−175.3 (5)	C21—C14—C15—C16	133.6 (8)
O3—C5—C6—C7	−65.8 (6)	C21'—C14—C15—C20	−128.6 (10)
N3—C5—C6—C7	112.3 (5)	N3—C14—C15—C20	92.4 (7)
C3—C2—C7—C8	−108.8 (5)	C21—C14—C15—C20	−46.4 (10)
C1—C2—C7—C8	72.1 (6)	C20—C15—C16—C17	−0.5 (10)
C3—C2—C7—C6	121.9 (5)	C14—C15—C16—C17	179.5 (6)
C1—C2—C7—C6	−57.2 (6)	C15—C16—C17—C18	0.3 (12)
C5—C6—C7—C2	−50.3 (6)	C16—C17—C18—C19	0.0 (13)
C5—C6—C7—C8	−178.3 (4)	C17—C18—C19—C20	0.1 (13)
C2—C7—C8—C9	60.7 (7)	C16—C15—C20—C19	0.6 (11)
C6—C7—C8—C9	−170.9 (5)	C14—C15—C20—C19	−179.5 (7)
C2—C7—C8—C13	−122.2 (6)	C18—C19—C20—C15	−0.4 (12)
C6—C7—C8—C13	6.2 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.86	1.88	2.694 (3)	158
O2—H2···N2ii	0.82	1.87	2.681 (3)	170
N3—H3···O1iii	0.86	2.09	2.892 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.86	1.88	2.694 (3)	158
O2—H2⋯N2ii	0.82	1.87	2.681 (3)	170
N3—H3⋯O1iii	0.86	2.09	2.892 (3)	155

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