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

Mol-ecules of the title compound, C(13)H(11)N(3)O(3), are connected into centrosymmetric dimers via inter-molecular N-H⋯N hydrogen bonds, generating an R(2) (2)(8) motif. The pyrimidine and the phenyl rings are twisted with respect to each other by an inter-planar angle of 61.3 (1)°.

Related literature

For related metal complexes of the title compound, see: Wu et al. (2011 ▶).

Experimental

Crystal data

C13H11N3O3

M = 257.25

Triclinic,

a = 5.7387 (7) Å

b = 7.9037 (10) Å

c = 13.6496 (19) Å

α = 80.793 (12)°

β = 79.997 (11)°

γ = 77.426 (10)°

V = 590.24 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 295 K

0.5 × 0.3 × 0.1 mm

Data collection

Siemens P4 diffractometer

Absorption correction: ψ scan (XSCANS; Siemens, 1995 ▶) T min = 0.963, T max = 0.989

2727 measured reflections

2066 independent reflections

1427 reflections with I > 2σ(I)

R int = 0.037

3 standard reflections every 97 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.119

S = 1.04

2066 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.18 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/S1600536811025190/bt5561sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025190/bt5561Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811025190/bt5561Isup3.cml

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

C13H11N3O3	Z = 2
Mr = 257.25	F(000) = 268
Triclinic, P1	Dx = 1.447 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.7387 (7) Å	Cell parameters from 26 reflections
b = 7.9037 (10) Å	θ = 4.4–17.4°
c = 13.6496 (19) Å	µ = 0.11 mm−1
α = 80.793 (12)°	T = 295 K
β = 79.997 (11)°	Plate, colourless
γ = 77.426 (10)°	0.5 × 0.3 × 0.1 mm
V = 590.24 (13) Å3

Siemens P4 diffractometer	1427 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
graphite	θmax = 25.0°, θmin = 2.7°
ω scans	h = −6→1
Absorption correction: ψ scan (XSCANS; Siemens, 1995)	k = −9→9
Tmin = 0.963, Tmax = 0.989	l = −16→16
2727 measured reflections	3 standard reflections every 97 reflections
2066 independent reflections	intensity decay: none

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.043P)2 + 0.2307P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2066 reflections	Δρmax = 0.21 e Å−3
174 parameters	Δρmin = −0.18 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.035 (5)

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
C1	0.3108 (4)	0.2690 (3)	1.01131 (16)	0.0434 (5)
C2	0.4585 (5)	0.1585 (3)	1.15496 (18)	0.0526 (6)
H2A	0.5531	0.1622	1.2032	0.063*
C3	0.3398 (5)	0.0224 (3)	1.16664 (19)	0.0556 (7)
H3A	0.3510	−0.0647	1.2211	0.067*
C4	0.2038 (5)	0.0214 (3)	1.09384 (19)	0.0569 (7)
H4A	0.1188	−0.0682	1.0999	0.068*
C5	0.1708 (4)	0.4275 (3)	0.85404 (17)	0.0441 (5)
C6	0.2691 (4)	0.5254 (3)	0.75767 (16)	0.0410 (5)
C7	0.5130 (4)	0.4939 (3)	0.71956 (17)	0.0448 (6)
H7A	0.6229	0.4185	0.7570	0.054*
C8	0.5926 (4)	0.5745 (3)	0.62600 (17)	0.0449 (6)
H8A	0.7555	0.5503	0.6000	0.054*
C9	0.4323 (4)	0.6908 (3)	0.57060 (16)	0.0426 (5)
C10	0.1888 (4)	0.7234 (3)	0.60887 (18)	0.0493 (6)
H10A	0.0797	0.8015	0.5722	0.059*
C11	0.1086 (4)	0.6399 (3)	0.70134 (17)	0.0474 (6)
H11A	−0.0552	0.6608	0.7261	0.057*
C12	0.5146 (4)	0.7860 (3)	0.47167 (17)	0.0473 (6)
C13	0.8539 (5)	0.8302 (4)	0.35163 (19)	0.0626 (7)
H13A	1.0257	0.8119	0.3490	0.094*
H13B	0.7869	0.9530	0.3485	0.094*
H13C	0.8174	0.7856	0.2959	0.094*
N1	0.4459 (3)	0.2859 (2)	1.07831 (14)	0.0469 (5)
N2	0.1882 (4)	0.1440 (3)	1.01460 (15)	0.0558 (6)
N3	0.3151 (4)	0.3953 (3)	0.92751 (14)	0.0496 (5)
H3B	0.4202	0.4605	0.9213	0.059*
O1	−0.0197 (3)	0.3799 (2)	0.86197 (13)	0.0601 (5)
O2	0.7514 (3)	0.7402 (2)	0.44414 (12)	0.0576 (5)
O3	0.3845 (3)	0.8936 (3)	0.42251 (14)	0.0690 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0482 (13)	0.0487 (13)	0.0364 (12)	−0.0176 (11)	−0.0042 (10)	−0.0053 (10)
C2	0.0638 (16)	0.0542 (15)	0.0436 (13)	−0.0143 (12)	−0.0160 (12)	−0.0048 (11)
C3	0.0678 (17)	0.0504 (15)	0.0466 (14)	−0.0158 (12)	−0.0070 (12)	0.0044 (11)
C4	0.0648 (17)	0.0553 (15)	0.0551 (15)	−0.0292 (13)	−0.0085 (13)	0.0032 (12)
C5	0.0487 (14)	0.0462 (13)	0.0419 (12)	−0.0162 (11)	−0.0083 (10)	−0.0077 (10)
C6	0.0493 (14)	0.0412 (12)	0.0381 (12)	−0.0155 (10)	−0.0109 (10)	−0.0071 (9)
C7	0.0458 (13)	0.0476 (13)	0.0442 (13)	−0.0128 (10)	−0.0150 (10)	−0.0010 (10)
C8	0.0412 (13)	0.0498 (13)	0.0459 (13)	−0.0123 (10)	−0.0097 (10)	−0.0045 (11)
C9	0.0510 (14)	0.0445 (12)	0.0379 (12)	−0.0160 (10)	−0.0116 (10)	−0.0070 (10)
C10	0.0514 (14)	0.0501 (14)	0.0482 (14)	−0.0086 (11)	−0.0197 (11)	0.0001 (11)
C11	0.0422 (13)	0.0550 (14)	0.0473 (14)	−0.0130 (11)	−0.0093 (10)	−0.0051 (11)
C12	0.0557 (15)	0.0496 (14)	0.0422 (13)	−0.0179 (12)	−0.0141 (11)	−0.0046 (11)
C13	0.0716 (18)	0.0643 (17)	0.0510 (15)	−0.0245 (14)	0.0011 (13)	−0.0002 (13)
N1	0.0571 (12)	0.0483 (11)	0.0413 (11)	−0.0194 (9)	−0.0127 (9)	−0.0044 (9)
N2	0.0666 (14)	0.0570 (13)	0.0529 (13)	−0.0319 (11)	−0.0148 (10)	0.0009 (10)
N3	0.0625 (13)	0.0563 (12)	0.0405 (11)	−0.0326 (10)	−0.0164 (9)	0.0013 (9)
O1	0.0508 (10)	0.0784 (12)	0.0559 (11)	−0.0290 (9)	−0.0113 (8)	0.0042 (9)
O2	0.0591 (11)	0.0611 (11)	0.0489 (10)	−0.0155 (9)	−0.0034 (8)	0.0043 (8)
O3	0.0674 (12)	0.0794 (13)	0.0560 (11)	−0.0142 (10)	−0.0207 (9)	0.0166 (10)

C1—N2	1.323 (3)	C7—H7A	0.9300
C1—N1	1.336 (3)	C8—C9	1.384 (3)
C1—N3	1.393 (3)	C8—H8A	0.9300
C2—N1	1.331 (3)	C9—C10	1.387 (3)
C2—C3	1.369 (4)	C9—C12	1.490 (3)
C2—H2A	0.9300	C10—C11	1.380 (3)
C3—C4	1.368 (4)	C10—H10A	0.9300
C3—H3A	0.9300	C11—H11A	0.9300
C4—N2	1.333 (3)	C12—O3	1.202 (3)
C4—H4A	0.9300	C12—O2	1.331 (3)
C5—O1	1.213 (3)	C13—O2	1.443 (3)
C5—N3	1.368 (3)	C13—H13A	0.9600
C5—C6	1.501 (3)	C13—H13B	0.9600
C6—C11	1.385 (3)	C13—H13C	0.9600
C6—C7	1.389 (3)	N3—H3B	0.8600
C7—C8	1.382 (3)
N2—C1—N1	127.4 (2)	C8—C9—C10	119.4 (2)
N2—C1—N3	118.7 (2)	C8—C9—C12	121.8 (2)
N1—C1—N3	113.84 (19)	C10—C9—C12	118.8 (2)
N1—C2—C3	123.5 (2)	C11—C10—C9	120.0 (2)
N1—C2—H2A	118.3	C11—C10—H10A	120.0
C3—C2—H2A	118.3	C9—C10—H10A	120.0
C4—C3—C2	116.4 (2)	C10—C11—C6	120.8 (2)
C4—C3—H3A	121.8	C10—C11—H11A	119.6
C2—C3—H3A	121.8	C6—C11—H11A	119.6
N2—C4—C3	122.6 (2)	O3—C12—O2	123.4 (2)
N2—C4—H4A	118.7	O3—C12—C9	124.5 (2)
C3—C4—H4A	118.7	O2—C12—C9	112.1 (2)
O1—C5—N3	124.8 (2)	O2—C13—H13A	109.5
O1—C5—C6	120.6 (2)	O2—C13—H13B	109.5
N3—C5—C6	114.57 (19)	H13A—C13—H13B	109.5
C11—C6—C7	119.2 (2)	O2—C13—H13C	109.5
C11—C6—C5	118.7 (2)	H13A—C13—H13C	109.5
C7—C6—C5	121.9 (2)	H13B—C13—H13C	109.5
C8—C7—C6	120.0 (2)	C2—N1—C1	114.5 (2)
C8—C7—H7A	120.0	C1—N2—C4	115.6 (2)
C6—C7—H7A	120.0	C5—N3—C1	127.31 (19)
C7—C8—C9	120.6 (2)	C5—N3—H3B	116.3
C7—C8—H8A	119.7	C1—N3—H3B	116.3
C9—C8—H8A	119.7	C12—O2—C13	117.09 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···N1i	0.86	2.30	3.104 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯N1i	0.86	2.30	3.104 (3)	156

Symmetry code: (i) .