Methyl 4-[(pyrimidin-2-yl)carbamo­yl]benzoate

Lu, C.-H.; Wu, C.-J.; Yeh, C.-W.; Hu, H.-L.; Chen, J.-D.

doi:10.1107/S1600536811025190

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1858

doi:10.1107/S1600536811025190

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Methyl 4-[(pyrimidin-2-yl)carbamoyl]benzoate

Chun-Hsiang Lu,^a Chia-Jun Wu,^a Chun-Wei Yeh,^a Hui-Ling Hu ^b and Jhy-Der Chen ^a ^*

^aDepartment of Chemistry, Chung-Yuan Christian University, Chung-Li, Taiwan, and ^bDepartment of Chemical and Materials Engineering, Nanya Institute of Technology, Chung-Li, Taiwan
^*Correspondence e-mail: jdchen@cycu.edu.tw

(Received 24 June 2011; accepted 27 June 2011; online 30 June 2011)

Molecules of the title compound, C₁₃H₁₁N₃O₃, are connected into centrosymmetric dimers via intermolecular N—H⋯N hydrogen bonds, generating an R₂²(8) motif. The pyrimidine and the phenyl rings are twisted with respect to each other by an interplanar 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_r = 257.25
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.119
S = 1.04
2066 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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) -x+1, -y+1, -z+2.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811025190/bt5561sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811025190/bt5561Isup3.cml

checkCIF report

Comment top

The silver(I) complex containg methyl-4-(pyrimidin-2-ylcarbamoyl)benzoate ligand has been reported, which shows one-dimensional structure (Wu et al., 2011). Within this project the crystal structure of the title compound was determined. In its crystal structure intermolecular N—H···N hydrogen bonds are found (Tab. 1).

Related literature top

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

Experimental top

The title compound was prepared according to a published procedure (Wu et al., 2011). Plate like crystals suitable for X-ray crystallography were obtained by slow evaporization of the solvent from a solution of the title compound in methanol.

Computing details top

Data collection: XSCANS (Siemens, 1995); cell refinement: XSCANS (Siemens, 1995); 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 (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Crystal structure of the title compound with atom labeling and displacement ellipsoids drawn at the 30% probability level.

Methyl 4-[(pyrimidin-2-yl)carbamoyl]benzoate top

Crystal data top

C₁₃H₁₁N₃O₃	Z = 2
M_r = 257.25	F(000) = 268
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.043P)² + 0.2307P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2066 reflections	Δρ_max = 0.21 e Å⁻³
174 parameters	Δρ_min = −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)

Crystal data top

C₁₃H₁₁N₃O₃	γ = 77.426 (10)°
M_r = 257.25	V = 590.24 (13) Å³
Triclinic, P1	Z = 2
a = 5.7387 (7) Å	Mo Kα radiation
b = 7.9037 (10) Å	µ = 0.11 mm⁻¹
c = 13.6496 (19) Å	T = 295 K
α = 80.793 (12)°	0.5 × 0.3 × 0.1 mm
β = 79.997 (11)°

Data collection top

Siemens P4 diffractometer	1427 reflections with I > 2σ(I)
Absorption correction: ψ scan (XSCANS; Siemens, 1995)	R_int = 0.037
T_min = 0.963, T_max = 0.989	3 standard reflections every 97 reflections
2727 measured reflections	intensity decay: none
2066 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.04	Δρ_max = 0.21 e Å⁻³
2066 reflections	Δρ_min = −0.18 e Å⁻³
174 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
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁N₃O₃
M_r	257.25
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	5.7387 (7), 7.9037 (10), 13.6496 (19)
α, β, γ (°)	80.793 (12), 79.997 (11), 77.426 (10)
V (Å³)	590.24 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.5 × 0.3 × 0.1

Data collection
Diffractometer	Siemens P4 diffractometer
Absorption correction	ψ scan (XSCANS; Siemens, 1995)
T_min, T_max	0.963, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	2727, 2066, 1427
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.119, 1.04
No. of reflections	2066
No. of parameters	174
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.18

Computer programs: XSCANS (Siemens, 1995), SHELXTL (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···N1ⁱ	0.860	2.299	3.104 (3)	156

Symmetry code: (i) −x+1, −y+1, −z+2.

Acknowledgements

We are grateful to the National Science Council of the Republic of China for support.

References

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1995). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Wu, C.-J., Sie, M.-J., Hsiao, H.-L. & Chen, J.-D. (2011). CrystEngComm, 13, 4121–4130. Web of Science CSD CrossRef CAS Google Scholar