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

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.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.113
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

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Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.07 Ratio
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

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

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

S2. Experimental

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.

S3. Refinement

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

Computing details

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

	Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids.
	Fig. 2. The crystal packing of (I), viewed along b axis. Hydrogen bonds are indicated by dashed lines.

methyl 2-(thiazol-2-ylcarbamoyl)benzoate

Crystal data

C12H10N2O3S	F(000) = 1088
Mr = 262.28	Dx = 1.387 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3562 reflections
a = 14.921 (7) Å	θ = 2.6–25.8°
b = 8.885 (5) Å	µ = 0.26 mm^−1
c = 18.954 (10) Å	T = 294 K
V = 2513 (2) Å^3	Block, light yellow
Z = 8	0.24 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer	2608 independent reflections
Radiation source: fine-focus sealed tube	1727 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
φ and ω scans	θmax = 26.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −9→18
Tmin = 0.941, Tmax = 0.950	k = −11→10
13481 measured reflections	l = −23→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0535P)^2 + 0.5869P] where P = (Fo^2 + 2Fc^2)/3
2608 reflections	(Δ/σ)max < 0.001
168 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.73851 (3)	0.02588 (8)	0.42504 (3)	0.0567 (2)
N2	0.55727 (10)	0.07951 (18)	0.41824 (8)	0.0384 (4)
O1	0.63380 (10)	0.1711 (2)	0.32477 (8)	0.0662 (5)
O2	0.54989 (12)	0.43035 (19)	0.41001 (10)	0.0751 (5)
O3	0.44802 (11)	0.59151 (18)	0.37036 (9)	0.0646 (5)
N1	0.61790 (10)	−0.0419 (2)	0.51622 (9)	0.0471 (4)
C1	0.77031 (14)	−0.0651 (3)	0.50073 (12)	0.0654 (7)
H1	0.8289	−0.0922	0.5116	0.078*
C2	0.69962 (14)	−0.0916 (3)	0.54175 (12)	0.0585 (6)
H2	0.7048	−0.1405	0.5849	0.070*
C3	0.62959 (12)	0.0223 (2)	0.45511 (9)	0.0364 (4)
C4	0.56328 (12)	0.1532 (2)	0.35544 (10)	0.0399 (5)
C5	0.47413 (12)	0.1974 (2)	0.32457 (9)	0.0380 (4)
C6	0.42858 (14)	0.0902 (2)	0.28470 (10)	0.0485 (5)
H6	0.4521	−0.0063	0.2801	0.058*
C7	0.34829 (16)	0.1262 (3)	0.25173 (11)	0.0598 (6)
H7	0.3182	0.0538	0.2254	0.072*
C8	0.31331 (16)	0.2682 (3)	0.25796 (13)	0.0659 (7)
H8	0.2598	0.2922	0.2355	0.079*
C9	0.35732 (15)	0.3755 (3)	0.29740 (12)	0.0569 (6)
H9	0.3332	0.4716	0.3014	0.068*
C10	0.43748 (12)	0.3416 (2)	0.33131 (9)	0.0397 (5)
C11	0.48523 (14)	0.4555 (2)	0.37476 (11)	0.0453 (5)
C12	0.4931 (2)	0.7107 (3)	0.40852 (16)	0.0859 (9)
H12A	0.5015	0.6807	0.4567	0.129*
H12B	0.4573	0.8004	0.4069	0.129*
H12C	0.5503	0.7299	0.3872	0.129*
H2A	0.5057 (14)	0.075 (2)	0.4383 (10)	0.042 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0282 (3)	0.0935 (5)	0.0485 (3)	0.0046 (3)	0.0109 (2)	0.0111 (3)
N2	0.0248 (8)	0.0530 (10)	0.0373 (9)	−0.0002 (7)	0.0078 (7)	0.0077 (7)
O1	0.0361 (8)	0.1083 (13)	0.0543 (9)	−0.0039 (8)	0.0139 (7)	0.0255 (9)
O2	0.0716 (12)	0.0633 (11)	0.0904 (13)	−0.0096 (9)	−0.0457 (10)	−0.0053 (9)
O3	0.0687 (11)	0.0502 (10)	0.0749 (11)	−0.0021 (8)	−0.0053 (8)	−0.0082 (8)
N1	0.0304 (8)	0.0699 (12)	0.0412 (9)	0.0042 (8)	0.0065 (7)	0.0133 (8)
C1	0.0334 (12)	0.106 (2)	0.0564 (14)	0.0159 (12)	0.0024 (10)	0.0109 (13)
C2	0.0372 (12)	0.0905 (18)	0.0479 (12)	0.0139 (12)	0.0010 (10)	0.0168 (12)
C3	0.0275 (9)	0.0450 (11)	0.0366 (10)	0.0005 (8)	0.0050 (7)	−0.0006 (9)
C4	0.0342 (10)	0.0509 (12)	0.0347 (10)	−0.0026 (9)	0.0054 (8)	0.0018 (9)
C5	0.0349 (10)	0.0505 (12)	0.0286 (9)	−0.0086 (9)	0.0035 (7)	0.0050 (9)
C6	0.0549 (13)	0.0525 (13)	0.0380 (11)	−0.0120 (10)	0.0037 (9)	−0.0016 (9)
C7	0.0609 (14)	0.0755 (17)	0.0430 (12)	−0.0280 (13)	−0.0145 (10)	−0.0002 (12)
C8	0.0515 (14)	0.0804 (18)	0.0659 (15)	−0.0114 (13)	−0.0307 (12)	0.0148 (13)
C9	0.0478 (13)	0.0577 (14)	0.0651 (14)	−0.0021 (11)	−0.0173 (10)	0.0106 (12)
C10	0.0354 (10)	0.0463 (12)	0.0374 (10)	−0.0095 (9)	−0.0060 (8)	0.0060 (8)
C11	0.0450 (12)	0.0468 (13)	0.0441 (11)	−0.0098 (10)	−0.0016 (9)	0.0045 (9)
C12	0.104 (2)	0.0569 (17)	0.097 (2)	−0.0212 (15)	0.0113 (18)	−0.0230 (15)

Geometric parameters (Å, º)

S1—C1	1.714 (2)	C5—C6	1.393 (3)
S1—C3	1.7224 (19)	C5—C10	1.399 (3)
N2—C4	1.362 (2)	C6—C7	1.389 (3)
N2—C3	1.382 (2)	C6—H6	0.9300
N2—H2A	0.86 (2)	C7—C8	1.370 (3)
O1—C4	1.213 (2)	C7—H7	0.9300
O2—C11	1.194 (2)	C8—C9	1.378 (3)
O3—C11	1.333 (3)	C8—H8	0.9300
O3—C12	1.448 (3)	C9—C10	1.391 (3)
N1—C3	1.303 (2)	C9—H9	0.9300
N1—C2	1.384 (3)	C10—C11	1.487 (3)
C1—C2	1.331 (3)	C12—H12A	0.9600
C1—H1	0.9300	C12—H12B	0.9600
C2—H2	0.9300	C12—H12C	0.9600
C4—C5	1.505 (3)
C1—S1—C3	88.60 (10)	C5—C6—H6	119.8
C4—N2—C3	124.56 (16)	C8—C7—C6	120.1 (2)
C4—N2—H2A	117.9 (13)	C8—C7—H7	119.9
C3—N2—H2A	117.3 (13)	C6—C7—H7	119.9
C11—O3—C12	116.0 (2)	C7—C8—C9	120.1 (2)
C3—N1—C2	109.42 (16)	C7—C8—H8	119.9
C2—C1—S1	110.66 (17)	C9—C8—H8	119.9
C2—C1—H1	124.7	C8—C9—C10	120.7 (2)
S1—C1—H1	124.7	C8—C9—H9	119.6
C1—C2—N1	115.9 (2)	C10—C9—H9	119.6
C1—C2—H2	122.0	C9—C10—C5	119.50 (18)
N1—C2—H2	122.0	C9—C10—C11	121.4 (2)
N1—C3—N2	120.38 (16)	C5—C10—C11	119.11 (17)
N1—C3—S1	115.37 (14)	O2—C11—O3	122.7 (2)
N2—C3—S1	124.23 (14)	O2—C11—C10	124.7 (2)
O1—C4—N2	122.64 (18)	O3—C11—C10	112.52 (18)
O1—C4—C5	123.11 (17)	O3—C12—H12A	109.5
N2—C4—C5	114.02 (15)	O3—C12—H12B	109.5
C6—C5—C10	119.03 (18)	H12A—C12—H12B	109.5
C6—C5—C4	117.61 (18)	O3—C12—H12C	109.5
C10—C5—C4	123.30 (17)	H12A—C12—H12C	109.5
C7—C6—C5	120.5 (2)	H12B—C12—H12C	109.5
C7—C6—H6	119.8
C3—S1—C1—C2	0.3 (2)	C4—C5—C6—C7	−176.65 (17)
S1—C1—C2—N1	−0.2 (3)	C5—C6—C7—C8	0.3 (3)
C3—N1—C2—C1	0.0 (3)	C6—C7—C8—C9	−0.5 (4)
C2—N1—C3—N2	179.05 (18)	C7—C8—C9—C10	0.0 (4)
C2—N1—C3—S1	0.2 (2)	C8—C9—C10—C5	0.7 (3)
C4—N2—C3—N1	177.45 (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—C9	176.01 (18)
C1—S1—C3—N2	−179.07 (18)	C6—C5—C10—C11	179.03 (17)
C3—N2—C4—O1	2.5 (3)	C4—C5—C10—C11	−4.1 (3)
C3—N2—C4—C5	177.13 (17)	C12—O3—C11—O2	2.8 (3)
O1—C4—C5—C6	90.0 (2)	C12—O3—C11—C10	−177.14 (19)
N2—C4—C5—C6	−84.6 (2)	C9—C10—C11—O2	173.3 (2)
O1—C4—C5—C10	−87.0 (3)	C5—C10—C11—O2	−6.7 (3)
N2—C4—C5—C10	98.4 (2)	C9—C10—C11—O3	−6.8 (3)
C10—C5—C6—C7	0.4 (3)	C5—C10—C11—O3	173.25 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1^i	0.86 (2)	2.06 (2)	2.913 (3)	175
C9—H9···O3	0.93	2.40	2.725 (3)	100

Symmetry code: (i) −x+1, −y, −z+1.