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

Mol-ecules of the title compound, C(13)H(10)ClN(3)O(3), form centrosymmetric dimers via inter-molecular N-H⋯N hydrogen bonds generating an R(2) (2)(8) motif. The dimers are further connected through an O⋯Cl-C halogen bond [O⋯Cl = 3.233 (1) Å and O⋯Cl-C = 167.33 (1)°] into a chain along [110]. The secondary amide group adopts a cis conformation. Weak C-H⋯N hydrogen bonds among the methyl benzoate and pyrimidyl rings are also observed in the crystal structure.

Related literature

For silver complexes of the title compound, see: Wu et al. (2011 ▶). For the conformation of the amide group in similar compounds, see: Forbes et al. (2001 ▶); Oertli et al. (1992 ▶).

Experimental

Crystal data

C13H10ClN3O3

M = 291.69

Triclinic,

a = 5.9068 (8) Å

b = 7.3378 (9) Å

c = 15.816 (4) Å

α = 78.259 (14)°

β = 82.030 (13)°

γ = 67.986 (10)°

V = 620.78 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.32 mm−1

T = 295 K

0.5 × 0.4 × 0.3 mm

Data collection

Siemens P4 diffractometer

Absorption correction: ψ scan (XSCANS; Siemens, 1995 ▶) T min = 0.888, T max = 0.918

2811 measured reflections

2140 independent reflections

1715 reflections with I > 2σ(I)

R int = 0.026

3 standard reflections every 97 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.098

S = 1.02

2140 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.21 e Å−3

Data collection: XSCANS (Siemens, 1995 ▶); cell refinement: XSCANS; data reduction: XSCANS; 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 datablock(s) I, global. DOI: 10.1107/S1600536811025268/gk2391sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025268/gk2391Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811025268/gk2391Isup3.cml

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

C13H10ClN3O3	Z = 2
Mr = 291.69	F(000) = 300
Triclinic, P1	Dx = 1.560 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9068 (8) Å	Cell parameters from 28 reflections
b = 7.3378 (9) Å	θ = 4.7–13.3°
c = 15.816 (4) Å	µ = 0.32 mm−1
α = 78.259 (14)°	T = 295 K
β = 82.030 (13)°	Block, colourless
γ = 67.986 (10)°	0.5 × 0.4 × 0.3 mm
V = 620.78 (19) Å3

Siemens P4 diffractometer	1715 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
graphite	θmax = 25.0°, θmin = 2.6°
ω scans	h = −1→7
Absorption correction: ψ scan (XSCANS; Siemens, 1995)	k = −8→8
Tmin = 0.888, Tmax = 0.918	l = −18→18
2811 measured reflections	3 standard reflections every 97 reflections
2140 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0507P)2 + 0.1938P] where P = (Fo2 + 2Fc2)/3
2140 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Experimental. 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.

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
Cl	0.10131 (12)	0.38338 (9)	0.11742 (4)	0.0550 (2)
C1	0.3775 (4)	0.5274 (3)	0.18741 (12)	0.0397 (5)
H1A	0.3782	0.4287	0.2349	0.048*
C2	0.2528 (4)	0.5446 (3)	0.11729 (12)	0.0367 (5)
C3	0.2556 (4)	0.6923 (3)	0.04841 (13)	0.0431 (5)
H3A	0.1746	0.7055	−0.0001	0.052*
C4	0.4859 (4)	0.7890 (3)	0.12062 (11)	0.0325 (4)
C5	0.7163 (4)	0.9541 (3)	0.18183 (12)	0.0347 (4)
C6	0.6516 (4)	0.8916 (3)	0.27530 (11)	0.0318 (4)
C7	0.8388 (4)	0.8014 (3)	0.33151 (12)	0.0359 (5)
H7A	1.0007	0.7763	0.3104	0.043*
C8	0.7837 (4)	0.7492 (3)	0.41870 (12)	0.0363 (5)
H8A	0.9091	0.6881	0.4562	0.044*
C9	0.5424 (4)	0.7875 (3)	0.45062 (11)	0.0311 (4)
C10	0.3554 (4)	0.8838 (3)	0.39472 (12)	0.0347 (4)
H10A	0.1930	0.9141	0.4162	0.042*
C11	0.4102 (4)	0.9345 (3)	0.30739 (12)	0.0354 (5)
H11A	0.2848	0.9976	0.2701	0.043*
C12	0.4893 (4)	0.7203 (3)	0.54431 (12)	0.0331 (4)
C13	0.1836 (4)	0.6842 (3)	0.65241 (12)	0.0411 (5)
H13A	0.0194	0.6854	0.6568	0.062*
H13B	0.1925	0.7730	0.6878	0.062*
H13C	0.2932	0.5516	0.6718	0.062*
N1	0.4973 (3)	0.6482 (3)	0.18929 (10)	0.0408 (4)
N2	0.3709 (3)	0.8174 (3)	0.04906 (10)	0.0393 (4)
N3	0.6073 (3)	0.9194 (2)	0.11818 (10)	0.0378 (4)
H3B	0.6161	0.9910	0.0684	0.045*
O1	0.8550 (3)	1.0460 (3)	0.16089 (9)	0.0527 (4)
O2	0.6419 (3)	0.6464 (3)	0.59689 (9)	0.0512 (4)
O3	0.2527 (3)	0.7486 (2)	0.56330 (8)	0.0406 (4)

	U11	U22	U33	U12	U13	U23
Cl	0.0698 (4)	0.0616 (4)	0.0504 (3)	−0.0436 (3)	−0.0186 (3)	0.0026 (3)
C1	0.0561 (14)	0.0391 (11)	0.0274 (10)	−0.0232 (10)	−0.0099 (9)	0.0038 (8)
C2	0.0417 (12)	0.0423 (11)	0.0315 (10)	−0.0212 (10)	−0.0039 (9)	−0.0052 (8)
C3	0.0539 (13)	0.0585 (13)	0.0267 (10)	−0.0312 (11)	−0.0121 (9)	−0.0006 (9)
C4	0.0379 (11)	0.0393 (10)	0.0220 (9)	−0.0168 (9)	−0.0034 (8)	−0.0017 (7)
C5	0.0418 (11)	0.0381 (11)	0.0285 (10)	−0.0203 (9)	−0.0041 (8)	−0.0023 (8)
C6	0.0418 (11)	0.0350 (10)	0.0255 (9)	−0.0210 (9)	−0.0059 (8)	−0.0036 (8)
C7	0.0319 (11)	0.0478 (12)	0.0332 (10)	−0.0200 (9)	−0.0044 (8)	−0.0057 (8)
C8	0.0382 (11)	0.0443 (12)	0.0299 (10)	−0.0183 (9)	−0.0122 (8)	−0.0003 (8)
C9	0.0369 (11)	0.0347 (10)	0.0264 (9)	−0.0172 (9)	−0.0080 (8)	−0.0031 (7)
C10	0.0333 (11)	0.0424 (11)	0.0292 (10)	−0.0150 (9)	−0.0048 (8)	−0.0028 (8)
C11	0.0375 (12)	0.0425 (11)	0.0265 (10)	−0.0149 (9)	−0.0104 (8)	0.0007 (8)
C12	0.0392 (12)	0.0347 (10)	0.0287 (10)	−0.0165 (9)	−0.0085 (9)	−0.0024 (8)
C13	0.0477 (13)	0.0498 (12)	0.0272 (10)	−0.0225 (10)	−0.0024 (9)	0.0007 (9)
N1	0.0575 (11)	0.0432 (10)	0.0283 (9)	−0.0268 (9)	−0.0143 (8)	0.0047 (7)
N2	0.0504 (11)	0.0522 (11)	0.0224 (8)	−0.0285 (9)	−0.0084 (7)	0.0016 (7)
N3	0.0519 (11)	0.0469 (10)	0.0217 (8)	−0.0287 (9)	−0.0091 (7)	0.0045 (7)
O1	0.0702 (11)	0.0736 (11)	0.0343 (8)	−0.0522 (10)	−0.0029 (7)	−0.0013 (7)
O2	0.0452 (9)	0.0793 (11)	0.0298 (8)	−0.0269 (8)	−0.0155 (7)	0.0074 (7)
O3	0.0394 (8)	0.0553 (9)	0.0254 (7)	−0.0196 (7)	−0.0060 (6)	0.0043 (6)

Cl—C2	1.730 (2)	C7—H7A	0.9300
C1—N1	1.332 (3)	C8—C9	1.387 (3)
C1—C2	1.374 (3)	C8—H8A	0.9300
C1—H1A	0.9300	C9—C10	1.390 (3)
C2—C3	1.375 (3)	C9—C12	1.492 (3)
C3—N2	1.334 (3)	C10—C11	1.382 (3)
C3—H3A	0.9300	C10—H10A	0.9300
C4—N1	1.328 (2)	C11—H11A	0.9300
C4—N2	1.341 (2)	C12—O2	1.206 (2)
C4—N3	1.387 (2)	C12—O3	1.334 (2)
C5—O1	1.217 (2)	C13—O3	1.446 (2)
C5—N3	1.378 (3)	C13—H13A	0.9600
C5—C6	1.497 (3)	C13—H13B	0.9600
C6—C11	1.385 (3)	C13—H13C	0.9600
C6—C7	1.391 (3)	N3—H3B	0.8600
C7—C8	1.381 (3)
N1—C1—C2	121.82 (17)	C8—C9—C10	119.59 (17)
N1—C1—H1A	119.1	C8—C9—C12	119.08 (17)
C2—C1—H1A	119.1	C10—C9—C12	121.31 (17)
C1—C2—C3	117.43 (19)	C11—C10—C9	120.16 (18)
C1—C2—Cl	120.22 (15)	C11—C10—H10A	119.9
C3—C2—Cl	122.34 (16)	C9—C10—H10A	119.9
N2—C3—C2	122.04 (18)	C10—C11—C6	120.13 (18)
N2—C3—H3A	119.0	C10—C11—H11A	119.9
C2—C3—H3A	119.0	C6—C11—H11A	119.9
N1—C4—N2	126.16 (18)	O2—C12—O3	123.57 (18)
N1—C4—N3	119.57 (16)	O2—C12—C9	124.38 (19)
N2—C4—N3	114.23 (16)	O3—C12—C9	112.05 (16)
O1—C5—N3	118.93 (17)	O3—C13—H13A	109.5
O1—C5—C6	120.70 (17)	O3—C13—H13B	109.5
N3—C5—C6	120.25 (17)	H13A—C13—H13B	109.5
C11—C6—C7	119.85 (17)	O3—C13—H13C	109.5
C11—C6—C5	121.36 (17)	H13A—C13—H13C	109.5
C7—C6—C5	118.62 (18)	H13B—C13—H13C	109.5
C8—C7—C6	119.92 (19)	C4—N1—C1	116.57 (16)
C8—C7—H7A	120.0	C3—N2—C4	115.95 (16)
C6—C7—H7A	120.0	C5—N3—C4	131.10 (16)
C7—C8—C9	120.30 (18)	C5—N3—H3B	114.4
C7—C8—H8A	119.9	C4—N3—H3B	114.4
C9—C8—H8A	119.9	C12—O3—C13	116.21 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···N2i	0.86	2.10	2.959 (2)	176
C13—H13C···N1ii	0.96	2.57	3.339 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯N2i	0.86	2.10	2.959 (2)	176
C13—H13C⋯N1ii	0.96	2.57	3.339 (2)	138

Symmetry codes: (i) ; (ii) .