Methyl 4-[N-(5-bromo-pyrimidin-2-yl)carbamo-yl]benzoate.

In the title compound, C(13)H(10)BrN(3)O(3), the pyrimidine and benzene rings are twisted with an inter-planar angle of 58.4 (1)°. The secondary amide group adopts a cis conformation with an H-N-C-O torsion angle of 14.8 (1)°. In the crystal, mol-ecules are connected into inversion dimers via pairs of N-H⋯N hydrogen bonds, generating an R(2) (2)(8) motif. The dimers are further connected through a C-Br⋯O inter-action [3.136 (1) Å and 169.31 (1)°] into a chain along [110]. Weak C-H⋯N hydrogen bonds between the methyl benzoate groups and pyrimidine rings are also observed in the crystal structure.

Related literature

For methyl-4-(5-bromo­pyrimidin-2-ylcarbamo­yl)benzoate and its metal complexes, see: Wu et al. (2011 ▶). For the conformation of related amides, see Forbes et al. (2001 ▶); Oertli et al. (1992 ▶); Lu et al. (2011 ▶). For C—Br⋯O inter­actions, see: Rowland & Taylor (1996 ▶).

Experimental

Crystal data

C13H10BrN3O3

M = 336.15

Triclinic,

a = 5.9398 (6) Å

b = 7.4137 (7) Å

c = 15.897 (2) Å

α = 77.846 (9)°

β = 81.613 (7)°

γ = 68.185 (9)°

V = 633.58 (12) Å3

Z = 2

Mo Kα radiation

μ = 3.26 mm−1

T = 295 K

0.4 × 0.3 × 0.2 mm

Data collection

Siemens P4 diffractometer

Absorption correction: ψ scan (XSCANS; Siemens, 1995 ▶) T min = 0.953, T max = 0.984

2880 measured reflections

2192 independent reflections

1841 reflections with I > 2σ(I)

R int = 0.027

3 standard reflections every 97 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.076

S = 1.05

2192 reflections

186 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.41 e Å−3

Data collection: XSCANS (Siemens, 1995 ▶); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812032102/gw2122sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032102/gw2122Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812032102/gw2122Isup3.cml

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

C13H10BrN3O3	Z = 2
Mr = 336.15	F(000) = 336
Triclinic, P1	Dx = 1.762 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9398 (6) Å	Cell parameters from 26 reflections
b = 7.4137 (7) Å	θ = 4.9–13.5°
c = 15.897 (2) Å	µ = 3.26 mm−1
α = 77.846 (9)°	T = 295 K
β = 81.613 (7)°	Block, colourless
γ = 68.185 (9)°	0.4 × 0.3 × 0.2 mm
V = 633.58 (12) Å3

Siemens P4 diffractometer	1841 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 25.0°, θmin = 2.6°
ω scans	h = −6→1
Absorption correction: ψ scan (XSCANS; Siemens, 1995)	k = −8→8
Tmin = 0.953, Tmax = 0.984	l = −18→18
2880 measured reflections	3 standard reflections every 97 reflections
2192 independent reflections	intensity decay: none

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0258P)2 + 0.579P] where P = (Fo2 + 2Fc2)/3
2192 reflections	(Δ/σ)max < 0.001
186 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.41 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
Br	0.90598 (7)	0.62807 (6)	0.37876 (2)	0.04607 (14)
C1	0.5123 (6)	0.2085 (4)	0.37807 (18)	0.0302 (7)
C2	0.7390 (6)	0.3054 (5)	0.4494 (2)	0.0401 (8)
H2A	0.8184	0.2926	0.4978	0.048*
C3	0.7438 (6)	0.4513 (5)	0.3806 (2)	0.0341 (7)
C4	0.6228 (6)	0.4664 (5)	0.3101 (2)	0.0373 (8)
H4A	0.6241	0.5631	0.2622	0.045*
C5	0.2842 (6)	0.0432 (5)	0.3186 (2)	0.0346 (7)
C6	0.3460 (6)	0.1063 (4)	0.22515 (19)	0.0307 (7)
C7	0.5876 (6)	0.0638 (5)	0.1926 (2)	0.0354 (7)
H7A	0.7120	0.0004	0.2295	0.043*
C8	0.6427 (6)	0.1155 (5)	0.1058 (2)	0.0345 (7)
H8A	0.8040	0.0861	0.0840	0.041*
C9	0.4556 (6)	0.2120 (4)	0.05051 (18)	0.0298 (7)
C10	0.2152 (6)	0.2496 (5)	0.0825 (2)	0.0360 (8)
H10A	0.0907	0.3107	0.0455	0.043*
C11	0.1611 (6)	0.1958 (5)	0.1703 (2)	0.0358 (7)
H11A	0.0003	0.2202	0.1918	0.043*
C12	0.5083 (6)	0.2803 (5)	−0.0433 (2)	0.0329 (7)
C13	0.8156 (7)	0.3160 (5)	−0.1514 (2)	0.0426 (8)
H13A	0.9781	0.3168	−0.1554	0.064*
H13B	0.7063	0.4464	−0.1713	0.064*
H13C	0.8100	0.2271	−0.1864	0.064*
N1	0.6247 (5)	0.1816 (4)	0.44924 (16)	0.0370 (6)
N2	0.5040 (5)	0.3454 (4)	0.30896 (16)	0.0384 (7)
N3	0.3906 (5)	0.0797 (4)	0.38148 (17)	0.0342 (6)
O1	0.1470 (5)	−0.0495 (4)	0.34026 (15)	0.0528 (7)
O2	0.7440 (4)	0.2520 (3)	−0.06249 (13)	0.0405 (6)
O3	0.3578 (5)	0.3532 (4)	−0.09519 (15)	0.0528 (7)
H3A	0.383 (7)	0.012 (6)	0.431 (3)	0.048 (11)*

	U11	U22	U33	U12	U13	U23
Br	0.0571 (2)	0.0489 (2)	0.0434 (2)	−0.03436 (18)	−0.01250 (16)	0.00359 (15)
C1	0.0366 (18)	0.0300 (16)	0.0243 (16)	−0.0142 (14)	−0.0003 (13)	−0.0018 (12)
C2	0.048 (2)	0.052 (2)	0.0272 (17)	−0.0276 (18)	−0.0105 (15)	0.0027 (15)
C3	0.0395 (18)	0.0342 (17)	0.0308 (17)	−0.0177 (15)	−0.0031 (14)	−0.0009 (13)
C4	0.051 (2)	0.0373 (18)	0.0284 (17)	−0.0243 (17)	−0.0072 (15)	0.0032 (14)
C5	0.0408 (19)	0.0347 (17)	0.0309 (17)	−0.0198 (16)	0.0003 (14)	−0.0014 (14)
C6	0.0410 (19)	0.0309 (16)	0.0271 (16)	−0.0214 (14)	−0.0034 (14)	−0.0029 (13)
C7	0.0390 (19)	0.0389 (18)	0.0291 (17)	−0.0163 (15)	−0.0089 (14)	0.0020 (14)
C8	0.0333 (18)	0.0404 (18)	0.0318 (17)	−0.0164 (15)	−0.0023 (14)	−0.0042 (14)
C9	0.0382 (18)	0.0309 (16)	0.0241 (15)	−0.0169 (14)	−0.0059 (13)	−0.0015 (12)
C10	0.0368 (19)	0.0447 (19)	0.0307 (17)	−0.0196 (16)	−0.0090 (14)	−0.0013 (14)
C11	0.0332 (18)	0.0456 (19)	0.0337 (17)	−0.0206 (15)	−0.0035 (14)	−0.0042 (14)
C12	0.0383 (19)	0.0331 (17)	0.0310 (17)	−0.0171 (15)	−0.0070 (15)	−0.0018 (13)
C13	0.050 (2)	0.052 (2)	0.0258 (17)	−0.0240 (18)	−0.0018 (15)	0.0047 (15)
N1	0.0472 (17)	0.0451 (16)	0.0244 (13)	−0.0269 (14)	−0.0052 (12)	0.0033 (12)
N2	0.0566 (18)	0.0393 (15)	0.0264 (14)	−0.0267 (14)	−0.0134 (13)	0.0049 (12)
N3	0.0481 (17)	0.0404 (16)	0.0215 (13)	−0.0281 (14)	−0.0050 (12)	0.0037 (12)
O1	0.0677 (17)	0.0703 (18)	0.0384 (14)	−0.0513 (15)	0.0006 (12)	−0.0005 (12)
O2	0.0412 (14)	0.0524 (14)	0.0252 (11)	−0.0196 (11)	−0.0037 (10)	0.0059 (10)
O3	0.0464 (15)	0.0795 (19)	0.0324 (13)	−0.0284 (14)	−0.0129 (12)	0.0089 (12)

Br—C3	1.887 (3)	C7—H7A	0.9300
C1—N2	1.322 (4)	C8—C9	1.395 (4)
C1—N1	1.339 (4)	C8—H8A	0.9300
C1—N3	1.385 (4)	C9—C10	1.388 (4)
C2—N1	1.329 (4)	C9—C12	1.498 (4)
C2—C3	1.372 (4)	C10—C11	1.392 (4)
C2—H2A	0.9300	C10—H10A	0.9300
C3—C4	1.382 (4)	C11—H11A	0.9300
C4—N2	1.336 (4)	C12—O3	1.200 (4)
C4—H4A	0.9300	C12—O2	1.335 (4)
C5—O1	1.220 (4)	C13—O2	1.448 (4)
C5—N3	1.377 (4)	C13—H13A	0.9600
C5—C6	1.495 (4)	C13—H13B	0.9600
C6—C11	1.379 (4)	C13—H13C	0.9600
C6—C7	1.394 (5)	N3—H3A	0.84 (4)
C7—C8	1.377 (4)
N2—C1—N1	126.4 (3)	C10—C9—C8	120.0 (3)
N2—C1—N3	119.5 (3)	C10—C9—C12	118.8 (3)
N1—C1—N3	114.2 (3)	C8—C9—C12	121.2 (3)
N1—C2—C3	122.2 (3)	C9—C10—C11	119.8 (3)
N1—C2—H2A	118.9	C9—C10—H10A	120.1
C3—C2—H2A	118.9	C11—C10—H10A	120.1
C2—C3—C4	117.3 (3)	C6—C11—C10	120.0 (3)
C2—C3—Br	123.2 (2)	C6—C11—H11A	120.0
C4—C3—Br	119.6 (2)	C10—C11—H11A	120.0
N2—C4—C3	121.5 (3)	O3—C12—O2	123.8 (3)
N2—C4—H4A	119.2	O3—C12—C9	124.5 (3)
C3—C4—H4A	119.2	O2—C12—C9	111.7 (3)
O1—C5—N3	118.9 (3)	O2—C13—H13A	109.5
O1—C5—C6	120.4 (3)	O2—C13—H13B	109.5
N3—C5—C6	120.6 (3)	H13A—C13—H13B	109.5
C11—C6—C7	120.1 (3)	O2—C13—H13C	109.5
C11—C6—C5	119.0 (3)	H13A—C13—H13C	109.5
C7—C6—C5	120.7 (3)	H13B—C13—H13C	109.5
C8—C7—C6	120.2 (3)	C2—N1—C1	116.1 (3)
C8—C7—H7A	119.9	C1—N2—C4	116.5 (3)
C6—C7—H7A	119.9	C5—N3—C1	131.2 (3)
C7—C8—C9	119.8 (3)	C5—N3—H3A	115 (3)
C7—C8—H8A	120.1	C1—N3—H3A	113 (3)
C9—C8—H8A	120.1	C12—O2—C13	116.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N1i	0.84 (4)	2.14 (1)	2.98 (1)	175 (1)
C13—H13B···N2ii	0.96	2.58	3.37 (1)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N1i	0.84 (4)	2.14 (1)	2.98 (1)	175 (1)
C13—H13B⋯N2ii	0.96	2.58	3.37 (1)	139

Symmetry codes: (i) ; (ii) .