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Acta Cryst. (2007). E63, o2819    [ doi:10.1107/S1600536807021241 ]

Methyl 2-[N-(thiazol-2-yl)carbamoyl]benzoate

Z.-P. Liang, J. Li, A.-Y. Wan and H.-Q. Wang

Abstract top

In the title molecule, C12H10N2O3S, the dihedral angle between the thiazole ring and benzene ring is 87.5 (2)°. In the crystal structure, intermolecular N-H...N hydrogen bonds form centrosymmetric dimers. There is an intramolecular C-H...O interaction.

Comment top

Thiazole and its derivatives are widely used in the fields of biology and for the synthesis of antibiotic and antipyrotic materials. In this paper, the structure of the title compound, (I), is reported. The molecular structure of (I) is illustrated in Fig. 1. The bond lengths and angles of the title compound agree with those common to N-(2-Bromothiazol-5-ylmethyl)phthalimide (Li et al., 2006). The dihedral angle between the thiazole ring and benzene ring is 87.5 (2) °. In the crystal structure, centrosymmetric dimers are formed via intermolecular N—H···N hydrogen bonds (Fig. 2 and Table 1) and a weak intramolecular C—H···O hydrogen bond may influence the conformation of the molecule.

Related literature top

The bond lengths and angles of the title compound agree with those common to N-(2-romothiazol-5-ylmethyl)phthalimide (Li et al., 2006).

Experimental top

Isobenzofuran-1,3-dione (0.02 mol) in methanol (15 ml) was refluxed for 0.5 h, and then cooled. Thiazol-2-amine (0.02 mol) was added to the above solution and was refluxed for 4 h. After cooling, filtration and drying, the title compound was obtained. 10 mg of (I) was dissolved in 10 ml acetone, and the solution was kept at room temperature for 10 d. Natural evaporation gave light yellow single crystals of the title compound, suitable for X-ray analysis.

Refinement top

The H atoms bonded to C atoms were positioned geometrically (C—H = 0.93–0.96 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5 Ueq(methyl C). The H atom bonded to N2 was refined isotropically.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids.
[Figure 2] Fig. 2. The crystal packing of (I), viewed along b axis. Hydrogen bonds are indicated by dashed lines.
methyl 2-(thiazol-2-ylcarbamoyl)benzoate top
Crystal data top
C12H10N2O3SF(000) = 1088
Mr = 262.28Dx = 1.387 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3562 reflections
a = 14.921 (7) Åθ = 2.6–25.8°
b = 8.885 (5) ŵ = 0.26 mm−1
c = 18.954 (10) ÅT = 294 K
V = 2513 (2) Å3Block, light yellow
Z = 80.24 × 0.22 × 0.20 mm
Data collection top
Bruker SMART CCD
diffractometer		2608 independent reflections
Radiation source: fine-focus sealed tube1727 reflections with I > 2σ(I)
graphiteRint = 0.055
φ and ω scansθmax = 26.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		h = −9→18
Tmin = 0.941, Tmax = 0.950k = −11→10
13481 measured reflectionsl = −23→23
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0535P)2 + 0.5869P]
where P = (Fo2 + 2Fc2)/3
2608 reflections(Δ/σ)max < 0.001
168 parametersΔρmax = 0.21 e Å−3
0 restraintsΔρmin = −0.30 e Å−3
Crystal data top
C12H10N2O3SV = 2513 (2) Å3
Mr = 262.28Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 14.921 (7) ŵ = 0.26 mm−1
b = 8.885 (5) ÅT = 294 K
c = 18.954 (10) Å0.24 × 0.22 × 0.20 mm
Data collection top
Bruker SMART CCD
diffractometer		2608 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		1727 reflections with I > 2σ(I)
Tmin = 0.941, Tmax = 0.950Rint = 0.055
13481 measured reflectionsθmax = 26.5°
Refinement top
R[F2 > 2σ(F2)] = 0.040H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.113Δρmax = 0.21 e Å−3
S = 1.02Δρmin = −0.30 e Å−3
2608 reflectionsAbsolute structure: ?
168 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
S10.73851 (3)0.02588 (8)0.42504 (3)0.0567 (2)
N20.55727 (10)0.07951 (18)0.41824 (8)0.0384 (4)
O10.63380 (10)0.1711 (2)0.32477 (8)0.0662 (5)
O20.54989 (12)0.43035 (19)0.41001 (10)0.0751 (5)
O30.44802 (11)0.59151 (18)0.37036 (9)0.0646 (5)
N10.61790 (10)−0.0419 (2)0.51622 (9)0.0471 (4)
C10.77031 (14)−0.0651 (3)0.50073 (12)0.0654 (7)
H10.8289−0.09220.51160.078*
C20.69962 (14)−0.0916 (3)0.54175 (12)0.0585 (6)
H20.7048−0.14050.58490.070*
C30.62959 (12)0.0223 (2)0.45511 (9)0.0364 (4)
C40.56328 (12)0.1532 (2)0.35544 (10)0.0399 (5)
C50.47413 (12)0.1974 (2)0.32457 (9)0.0380 (4)
C60.42858 (14)0.0902 (2)0.28470 (10)0.0485 (5)
H60.4521−0.00630.28010.058*
C70.34829 (16)0.1262 (3)0.25173 (11)0.0598 (6)
H70.31820.05380.22540.072*
C80.31331 (16)0.2682 (3)0.25796 (13)0.0659 (7)
H80.25980.29220.23550.079*
C90.35732 (15)0.3755 (3)0.29740 (12)0.0569 (6)
H90.33320.47160.30140.068*
C100.43748 (12)0.3416 (2)0.33131 (9)0.0397 (5)
C110.48523 (14)0.4555 (2)0.37476 (11)0.0453 (5)
C120.4931 (2)0.7107 (3)0.40852 (16)0.0859 (9)
H12A0.50150.68070.45670.129*
H12B0.45730.80040.40690.129*
H12C0.55030.72990.38720.129*
H2A0.5057 (14)0.075 (2)0.4383 (10)0.042 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0282 (3)0.0935 (5)0.0485 (3)0.0046 (3)0.0109 (2)0.0111 (3)
N20.0248 (8)0.0530 (10)0.0373 (9)−0.0002 (7)0.0078 (7)0.0077 (7)
O10.0361 (8)0.1083 (13)0.0543 (9)−0.0039 (8)0.0139 (7)0.0255 (9)
O20.0716 (12)0.0633 (11)0.0904 (13)−0.0096 (9)−0.0457 (10)−0.0053 (9)
O30.0687 (11)0.0502 (10)0.0749 (11)−0.0021 (8)−0.0053 (8)−0.0082 (8)
N10.0304 (8)0.0699 (12)0.0412 (9)0.0042 (8)0.0065 (7)0.0133 (8)
C10.0334 (12)0.106 (2)0.0564 (14)0.0159 (12)0.0024 (10)0.0109 (13)
C20.0372 (12)0.0905 (18)0.0479 (12)0.0139 (12)0.0010 (10)0.0168 (12)
C30.0275 (9)0.0450 (11)0.0366 (10)0.0005 (8)0.0050 (7)−0.0006 (9)
C40.0342 (10)0.0509 (12)0.0347 (10)−0.0026 (9)0.0054 (8)0.0018 (9)
C50.0349 (10)0.0505 (12)0.0286 (9)−0.0086 (9)0.0035 (7)0.0050 (9)
C60.0549 (13)0.0525 (13)0.0380 (11)−0.0120 (10)0.0037 (9)−0.0016 (9)
C70.0609 (14)0.0755 (17)0.0430 (12)−0.0280 (13)−0.0145 (10)−0.0002 (12)
C80.0515 (14)0.0804 (18)0.0659 (15)−0.0114 (13)−0.0307 (12)0.0148 (13)
C90.0478 (13)0.0577 (14)0.0651 (14)−0.0021 (11)−0.0173 (10)0.0106 (12)
C100.0354 (10)0.0463 (12)0.0374 (10)−0.0095 (9)−0.0060 (8)0.0060 (8)
C110.0450 (12)0.0468 (13)0.0441 (11)−0.0098 (10)−0.0016 (9)0.0045 (9)
C120.104 (2)0.0569 (17)0.097 (2)−0.0212 (15)0.0113 (18)−0.0230 (15)
Geometric parameters (Å, °) top
S1—C11.714 (2)C5—C61.393 (3)
S1—C31.7224 (19)C5—C101.399 (3)
N2—C41.362 (2)C6—C71.389 (3)
N2—C31.382 (2)C6—H60.9300
N2—H2A0.86 (2)C7—C81.370 (3)
O1—C41.213 (2)C7—H70.9300
O2—C111.194 (2)C8—C91.378 (3)
O3—C111.333 (3)C8—H80.9300
O3—C121.448 (3)C9—C101.391 (3)
N1—C31.303 (2)C9—H90.9300
N1—C21.384 (3)C10—C111.487 (3)
C1—C21.331 (3)C12—H12A0.9600
C1—H10.9300C12—H12B0.9600
C2—H20.9300C12—H12C0.9600
C4—C51.505 (3)
?···??
C1—S1—C388.60 (10)C5—C6—H6119.8
C4—N2—C3124.56 (16)C8—C7—C6120.1 (2)
C4—N2—H2A117.9 (13)C8—C7—H7119.9
C3—N2—H2A117.3 (13)C6—C7—H7119.9
C11—O3—C12116.0 (2)C7—C8—C9120.1 (2)
C3—N1—C2109.42 (16)C7—C8—H8119.9
C2—C1—S1110.66 (17)C9—C8—H8119.9
C2—C1—H1124.7C8—C9—C10120.7 (2)
S1—C1—H1124.7C8—C9—H9119.6
C1—C2—N1115.9 (2)C10—C9—H9119.6
C1—C2—H2122.0C9—C10—C5119.50 (18)
N1—C2—H2122.0C9—C10—C11121.4 (2)
N1—C3—N2120.38 (16)C5—C10—C11119.11 (17)
N1—C3—S1115.37 (14)O2—C11—O3122.7 (2)
N2—C3—S1124.23 (14)O2—C11—C10124.7 (2)
O1—C4—N2122.64 (18)O3—C11—C10112.52 (18)
O1—C4—C5123.11 (17)O3—C12—H12A109.5
N2—C4—C5114.02 (15)O3—C12—H12B109.5
C6—C5—C10119.03 (18)H12A—C12—H12B109.5
C6—C5—C4117.61 (18)O3—C12—H12C109.5
C10—C5—C4123.30 (17)H12A—C12—H12C109.5
C7—C6—C5120.5 (2)H12B—C12—H12C109.5
C7—C6—H6119.8
C3—S1—C1—C20.3 (2)C4—C5—C6—C7−176.65 (17)
S1—C1—C2—N1−0.2 (3)C5—C6—C7—C80.3 (3)
C3—N1—C2—C10.0 (3)C6—C7—C8—C9−0.5 (4)
C2—N1—C3—N2179.05 (18)C7—C8—C9—C100.0 (4)
C2—N1—C3—S10.2 (2)C8—C9—C10—C50.7 (3)
C4—N2—C3—N1177.45 (19)C8—C9—C10—C11−179.2 (2)
C4—N2—C3—S1−3.8 (3)C6—C5—C10—C9−0.9 (3)
C1—S1—C3—N1−0.29 (18)C4—C5—C10—C9176.01 (18)
C1—S1—C3—N2−179.07 (18)C6—C5—C10—C11179.03 (17)
C3—N2—C4—O12.5 (3)C4—C5—C10—C11−4.1 (3)
C3—N2—C4—C5177.13 (17)C12—O3—C11—O22.8 (3)
O1—C4—C5—C690.0 (2)C12—O3—C11—C10−177.14 (19)
N2—C4—C5—C6−84.6 (2)C9—C10—C11—O2173.3 (2)
O1—C4—C5—C10−87.0 (3)C5—C10—C11—O2−6.7 (3)
N2—C4—C5—C1098.4 (2)C9—C10—C11—O3−6.8 (3)
C10—C5—C6—C70.4 (3)C5—C10—C11—O3173.25 (17)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N1i0.86 (2)2.06 (2)2.913 (3)175
C9—H9···O30.932.402.725 (3)100
Symmetry codes: (i) −x+1, −y, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N1i0.86 (2)2.06 (2)2.913 (3)175
C9—H9···O30.932.402.725 (3)100
Symmetry codes: (i) −x+1, −y, −z+1.
Acknowledgements top

This work was supported by the Doctoral Foundation of Weifang University.

references
References top

Bruker (1997). SADABS (Version 2.01), SMART (Version 5.044), SAINT (Version 5.01) and SHELXTL (Version 5.10). Bruker AXS Inc., Madison, Wisconsin, USA.

Li, J.-T., Wang, J.-K. & Zhou, L.-N. (2006). Acta Cryst. E62, o2327–o2328.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.