Methyl 2-(thio-phene-2-carboxamido)-benzoate.

The title compound, C(13)H(11)NO(3)S, was synthesized from methyl anthranilate, triethyl-amine and 2-thio-phenoyl chloride in benzene. The mol-ecular conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond. The dihedral angle between the rings is 2.74 (12)°. In the crystal, C-H⋯O inter-actions link neighbouring mol-ecules into a three-dimensional network.

Related literature

For the synthesis, see: Sladowska et al. (1980 ▶).

Experimental

Crystal data

C13H11NO3S

M = 261.29

Orthorhombic,

a = 19.2845 (4) Å

b = 3.86753 (8) Å

c = 15.6430 (3) Å

V = 1166.71 (4) Å3

Z = 4

Cu Kα radiation

μ = 2.48 mm−1

T = 123 K

0.45 × 0.18 × 0.04 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer

Absorption correction: analytical (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.573, T max = 0.908

2379 measured reflections

1422 independent reflections

1381 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.090

S = 1.04

1422 reflections

168 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.27 e Å−3

Absolute structure: Flack (1983 ▶), 206 Friedel pairs

Flack parameter: −0.02 (2)

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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/S160053681202082X/bt5852sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202082X/bt5852Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202082X/bt5852Isup3.cml

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

C13H11NO3S	F(000) = 544
Mr = 261.29	Dx = 1.488 Mg m−3
Orthorhombic, Pca21	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2c -2ac	Cell parameters from 1440 reflections
a = 19.2845 (4) Å	θ = 2.8–75.1°
b = 3.86753 (8) Å	µ = 2.48 mm−1
c = 15.6430 (3) Å	T = 123 K
V = 1166.71 (4) Å3	Needle, colorless
Z = 4	0.45 × 0.18 × 0.04 mm

Agilent Xcalibur Ruby Gemini diffractometer	1422 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1381 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 10.5081 pixels mm-1	θmax = 75.2°, θmin = 4.6°
ω scans	h = −15→23
Absorption correction: analytical (CrysAlis PRO; Agilent, 2012)	k = −4→4
Tmin = 0.573, Tmax = 0.908	l = −6→19
2379 measured reflections

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)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0597P)2 + 0.0898P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
1422 reflections	Δρmax = 0.21 e Å−3
168 parameters	Δρmin = −0.27 e Å−3
2 restraints	Absolute structure: Flack (1983), 206 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.02 (2)

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
S1	0.25886 (3)	0.20133 (16)	0.72770 (5)	0.03006 (19)
O1	0.28253 (10)	0.3657 (6)	0.54680 (14)	0.0304 (4)
O2	0.51080 (11)	0.8922 (6)	0.60945 (13)	0.0339 (5)
O3	0.57519 (10)	1.1406 (5)	0.50816 (14)	0.0308 (4)
N1	0.38872 (12)	0.6290 (6)	0.56315 (15)	0.0252 (5)
H1B	0.4151 (18)	0.698 (9)	0.603 (2)	0.037 (10)*
C1	0.29286 (16)	0.2186 (7)	0.8287 (2)	0.0307 (6)
H1A	0.2694	0.1372	0.8781	0.037*
C2	0.35685 (16)	0.3611 (8)	0.8301 (2)	0.0304 (6)
H2A	0.3831	0.3919	0.8810	0.037*
C3	0.38110 (14)	0.4607 (7)	0.74725 (17)	0.0249 (5)
H3A	0.4251	0.5621	0.7364	0.030*
C4	0.33202 (13)	0.3900 (7)	0.68499 (18)	0.0251 (5)
C5	0.33132 (14)	0.4577 (7)	0.59160 (18)	0.0247 (6)
C6	0.40520 (13)	0.7321 (7)	0.4797 (2)	0.0231 (5)
C7	0.36094 (14)	0.6720 (7)	0.41074 (19)	0.0262 (6)
H7A	0.3173	0.5642	0.4201	0.031*
C8	0.38002 (15)	0.7678 (7)	0.3290 (2)	0.0279 (6)
H8A	0.3498	0.7185	0.2826	0.034*
C9	0.44255 (15)	0.9352 (7)	0.31331 (18)	0.0277 (6)
H9A	0.4550	1.0010	0.2569	0.033*
C10	0.48604 (14)	1.0039 (7)	0.38091 (19)	0.0261 (6)
H10A	0.5284	1.1221	0.3708	0.031*
C11	0.46910 (13)	0.9032 (7)	0.46454 (18)	0.0241 (6)
C12	0.51909 (14)	0.9743 (7)	0.53544 (18)	0.0253 (5)
C13	0.62744 (16)	1.2115 (9)	0.5729 (2)	0.0359 (7)
H13A	0.6645	1.3525	0.5479	0.054*
H13B	0.6469	0.9929	0.5937	0.054*
H13C	0.6062	1.3367	0.6206	0.054*

	U11	U22	U33	U12	U13	U23
S1	0.0264 (3)	0.0293 (3)	0.0345 (4)	−0.0023 (2)	0.0046 (3)	0.0010 (4)
O1	0.0248 (9)	0.0361 (10)	0.0303 (10)	−0.0051 (8)	−0.0037 (8)	−0.0012 (9)
O2	0.0329 (10)	0.0454 (11)	0.0235 (10)	−0.0104 (9)	−0.0042 (9)	0.0033 (10)
O3	0.0254 (9)	0.0401 (11)	0.0268 (9)	−0.0077 (9)	−0.0033 (9)	0.0017 (9)
N1	0.0234 (10)	0.0295 (11)	0.0227 (11)	−0.0024 (9)	−0.0005 (9)	−0.0013 (9)
C1	0.0342 (14)	0.0284 (14)	0.0294 (15)	0.0026 (11)	0.0072 (12)	0.0021 (12)
C2	0.0341 (14)	0.0299 (13)	0.0272 (14)	0.0021 (12)	0.0037 (12)	0.0013 (12)
C3	0.0281 (12)	0.0242 (11)	0.0224 (12)	−0.0015 (10)	0.0044 (11)	0.0004 (10)
C4	0.0230 (12)	0.0226 (12)	0.0298 (14)	0.0020 (10)	0.0037 (11)	0.0009 (10)
C5	0.0245 (12)	0.0208 (12)	0.0288 (14)	0.0035 (10)	0.0019 (11)	0.0001 (10)
C6	0.0239 (13)	0.0211 (11)	0.0243 (12)	0.0017 (9)	0.0006 (11)	−0.0002 (11)
C7	0.0232 (12)	0.0263 (13)	0.0290 (15)	−0.0009 (10)	−0.0042 (12)	−0.0018 (11)
C8	0.0301 (13)	0.0282 (12)	0.0255 (14)	0.0035 (11)	−0.0094 (12)	−0.0020 (11)
C9	0.0333 (13)	0.0287 (14)	0.0210 (12)	0.0050 (11)	0.0007 (11)	0.0033 (11)
C10	0.0256 (12)	0.0251 (13)	0.0277 (14)	0.0007 (11)	0.0018 (11)	0.0005 (10)
C11	0.0239 (12)	0.0218 (11)	0.0267 (14)	0.0028 (10)	−0.0032 (11)	−0.0021 (11)
C12	0.0240 (12)	0.0260 (12)	0.0258 (13)	0.0006 (10)	−0.0017 (10)	−0.0011 (10)
C13	0.0292 (14)	0.0416 (17)	0.0370 (16)	−0.0082 (12)	−0.0090 (14)	0.0002 (15)

S1—C1	1.711 (3)	C4—C5	1.484 (4)
S1—C4	1.723 (3)	C6—C7	1.395 (4)
O1—C5	1.226 (3)	C6—C11	1.419 (3)
O2—C12	1.211 (4)	C7—C8	1.381 (4)
O3—C12	1.329 (3)	C7—H7A	0.9500
O3—C13	1.454 (4)	C8—C9	1.390 (4)
N1—C5	1.365 (4)	C8—H8A	0.9500
N1—C6	1.401 (4)	C9—C10	1.375 (4)
N1—H1B	0.852 (19)	C9—H9A	0.9500
C1—C2	1.352 (4)	C10—C11	1.404 (4)
C1—H1A	0.9500	C10—H10A	0.9500
C2—C3	1.431 (4)	C11—C12	1.495 (4)
C2—H2A	0.9500	C13—H13A	0.9800
C3—C4	1.385 (4)	C13—H13B	0.9800
C3—H3A	0.9500	C13—H13C	0.9800
C1—S1—C4	91.59 (15)	C8—C7—H7A	119.7
C12—O3—C13	115.6 (3)	C6—C7—H7A	119.7
C5—N1—C6	128.7 (2)	C7—C8—C9	121.3 (3)
C5—N1—H1B	113 (3)	C7—C8—H8A	119.4
C6—N1—H1B	117 (3)	C9—C8—H8A	119.4
C2—C1—S1	112.4 (2)	C10—C9—C8	118.9 (3)
C2—C1—H1A	123.8	C10—C9—H9A	120.6
S1—C1—H1A	123.8	C8—C9—H9A	120.6
C1—C2—C3	113.2 (3)	C9—C10—C11	121.4 (2)
C1—C2—H2A	123.4	C9—C10—H10A	119.3
C3—C2—H2A	123.4	C11—C10—H10A	119.3
C4—C3—C2	111.1 (2)	C10—C11—C6	119.2 (2)
C4—C3—H3A	124.4	C10—C11—C12	119.4 (2)
C2—C3—H3A	124.4	C6—C11—C12	121.4 (3)
C3—C4—C5	131.5 (2)	O2—C12—O3	122.8 (3)
C3—C4—S1	111.7 (2)	O2—C12—C11	125.2 (3)
C5—C4—S1	116.7 (2)	O3—C12—C11	112.1 (2)
O1—C5—N1	125.2 (3)	O3—C13—H13A	109.5
O1—C5—C4	121.2 (3)	O3—C13—H13B	109.5
N1—C5—C4	113.5 (2)	H13A—C13—H13B	109.5
C7—C6—N1	122.3 (2)	O3—C13—H13C	109.5
C7—C6—C11	118.6 (3)	H13A—C13—H13C	109.5
N1—C6—C11	119.1 (3)	H13B—C13—H13C	109.5
C8—C7—C6	120.6 (3)
C4—S1—C1—C2	0.0 (2)	C11—C6—C7—C8	2.0 (4)
S1—C1—C2—C3	−0.5 (3)	C6—C7—C8—C9	−1.9 (4)
C1—C2—C3—C4	0.8 (4)	C7—C8—C9—C10	0.3 (4)
C2—C3—C4—C5	177.1 (3)	C8—C9—C10—C11	1.2 (4)
C2—C3—C4—S1	−0.8 (3)	C9—C10—C11—C6	−1.1 (4)
C1—S1—C4—C3	0.4 (2)	C9—C10—C11—C12	178.1 (2)
C1—S1—C4—C5	−177.8 (2)	C7—C6—C11—C10	−0.5 (4)
C6—N1—C5—O1	−0.8 (5)	N1—C6—C11—C10	179.4 (3)
C6—N1—C5—C4	179.6 (2)	C7—C6—C11—C12	−179.7 (2)
C3—C4—C5—O1	178.3 (3)	N1—C6—C11—C12	0.2 (4)
S1—C4—C5—O1	−3.9 (4)	C13—O3—C12—O2	1.5 (4)
C3—C4—C5—N1	−2.1 (4)	C13—O3—C12—C11	−178.4 (2)
S1—C4—C5—N1	175.66 (19)	C10—C11—C12—O2	−178.1 (3)
C5—N1—C6—C7	1.1 (4)	C6—C11—C12—O2	1.0 (4)
C5—N1—C6—C11	−178.8 (3)	C10—C11—C12—O3	1.7 (4)
N1—C6—C7—C8	−177.9 (3)	C6—C11—C12—O3	−179.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2	0.85 (2)	1.99 (3)	2.665 (3)	135 (4)
C9—H9A···O2i	0.95	2.43	3.380 (3)	174
C13—H13A···O1ii	0.98	2.52	3.433 (4)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O2	0.85 (2)	1.99 (3)	2.665 (3)	135 (4)
C9—H9A⋯O2i	0.95	2.43	3.380 (3)	174
C13—H13A⋯O1ii	0.98	2.52	3.433 (4)	154

Symmetry codes: (i) ; (ii) .