3-(4-Bromo­phen­yl)-3-(4-hydr­oxy-6-oxo-1,6-dihydro­pyrimidin-5-yl)-N-[(S)-1-phenyl­ethyl]propanamide

Peng, J.-H.; Hao, W.-J.; Tu, S.-J.

doi:10.1107/S1600536809003821

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o489

doi:10.1107/S1600536809003821

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3-(4-Bromophenyl)-3-(4-hydroxy-6-oxo-1,6-dihydropyrimidin-5-yl)-N-[(S)-1-phenylethyl]propanamide

Ju-Hua Peng,^a Wen-Juan Hao ^b and Shu-Jiang Tu ^b ^*

^aLianyungang Teachers' College, Lianyungang 222006, People's Republic of China, and ^bSchool of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116, People's Republic of China
^*Correspondence e-mail: laotu2001@263.net

(Received 18 January 2009; accepted 1 February 2009; online 6 February 2009)

In the molecule of the title compound, C₂₁H₂₀BrN₃O₃, the pyrimidine ring is oriented at dihedral angles of 80.87 (3) and 15.99 (3)°, respectively, to the pyrimidine and bromophenyl rings. The dihedral angle between the two benzene rings is 88.37 (3)°. In the crystal structure, intermolecular N—H⋯O and O—H⋯N hydrogen bonds link the molecules. 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_r = 442.31
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.062
wR(F²) = 0.162
S = 1.06
3498 reflections
265 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.43 e Å⁻³

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) x+1, y, z; (ii) -x+1, -y+1, -z+2; (iii) -x+1, -y+1, -z+1.

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.

Supporting information

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

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

checkCIF report

Comment top

The pyrimidines and their derivatives as a class of extremely important heterocyclic compounds are used in a wide array of synthetic and industrial applications. Not only they are an integral part of the genetic materials, viz. DNA and RNA as nucleotides and nucleosides but also play critical roles especially in pharmaceutical fields (Johar et al., 2005; Janeba et al., 2005). Some pyrimidine derivatives can give stable and good quality nanomaterials having many important electrical and optical properties (Soloducho et al., 2003; Mathews & Asokan, 2007), and also used as functional materials (Lagoja, 2005; Michael, 2005; Erian, 1993). We report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (N1/N2/C1-C4), B (C8-C13) and C (C15-C20) are, of course, planar, and they are oriented at dihedral angles of A/B = 80.87 (3)°, A/C = 15.99 (3)° and B/C = 88.37 (3)°.

In the crystal structure, intermolecular N—H···O and O—H···N hydrogen bonds (Table 1) link the molecules, in which they may be effective in the stabilization of the structure. The π-π contact between the pyrimidine and the phenyl rings, Cg1—Cg2 [where Cg1 and Cg2 are centroids of the rings A (N1/N2/C1-C4) and C (C15-C20), respectively] may further stabilize the structure, with centroid-centroid distance of 3.776 (3) Å.

Related literature top

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 top

The title compound was prepared by the reaction of 4-bromophenylidene-Meldrum's acid (1 mmol) with 6-hydroxypyrimidin-4(3H)-one (1 mmol) and (S)-1-phenylethanamine (1 mmol) at 373 K in glacial acetic acid under microwave irradiation (maximum power 250 W, initial power 100 W) for 18 min (yield; 85%, m.p. 551–553 K). Crystals suitable for X-ray analysis were obtained from an ethanol solution by slow evaporation.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

3-(4-Bromophenyl)-3-(4-hydroxy-6-oxo-1,6-dihydropyrimidin-5-yl)-N- [(S)-1-phenylethyl]propanamide top

Crystal data top

C₂₁H₂₀BrN₃O₃	Z = 2
M_r = 442.31	F(000) = 452
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0673P)²] where P = (F_o² + 2F_c²)/3
3498 reflections	(Δ/σ)_max = 0.001
265 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₂₁H₂₀BrN₃O₃	γ = 93.074 (1)°
M_r = 442.31	V = 1004.0 (2) Å³
Triclinic, P1	Z = 2
a = 7.147 (1) Å	Mo Kα radiation
b = 12.5010 (14) Å	µ = 2.07 mm⁻¹
c = 13.0940 (16) Å	T = 298 K
α = 118.506 (2)°	0.20 × 0.18 × 0.17 mm
β = 99.047 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3498 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	1810 reflections with I > 2σ(I)
T_min = 0.682, T_max = 0.719	R_int = 0.029
5285 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 1.06	Δρ_max = 0.38 e Å⁻³
3498 reflections	Δρ_min = −0.43 e Å⁻³
265 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z; (ii) −x+1, −y+1, −z+2; (iii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₀BrN₃O₃
M_r	442.31
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.147 (1), 12.5010 (14), 13.0940 (16)
α, β, γ (°)	118.506 (2), 99.047 (1), 93.074 (1)
V (Å³)	1004.0 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.07
Crystal size (mm)	0.20 × 0.18 × 0.17

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.682, 0.719
No. of measured, independent and observed [I > 2σ(I)] reflections	5285, 3498, 1810
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.162, 1.06
No. of reflections	3498
No. of parameters	265
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.43

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z; (ii) −x+1, −y+1, −z+2; (iii) −x+1, −y+1, −z+1.

Acknowledgements

We thank the Natural Science Foundation of China (grant No. 20672090) and the Natural Science Foundation of Jiangsu Province (grant No. BK2006033) for support.

References

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Volume 65| Part 3| March 2009| Page o489

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-(4-Bromo­phen­yl)-3-(4-hydr­­oxy-6-oxo-1,6-di­hydro­pyrimidin-5-yl)-N-[(S)-1-phenyl­ethyl]propanamide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-(4-Bromophenyl)-3-(4-hydroxy-6-oxo-1,6-dihydropyrimidin-5-yl)-N-[(S)-1-phenylethyl]propanamide