2-Amino-N-(2-methoxy-phen-yl)-4,5-dimethyl-thio-phene-3-carboxamide.

In the title compound, C(14)H(16)N(2)O(2)S, the two aromatic rings make a dihedral angle of 13.9 (1)°. The crystal structure is stabilized by both inter- and intra-molecular N-H⋯O, C-H⋯O and C-H⋯N hydrogen bonds.

Related literature

For related literature, see: Gewald et al. (1966 ▶); Cohen et al. (1977 ▶); Csaszar & Morvay (1983 ▶); Lakshmi et al. (1985 ▶); Mohan & Saravanan (2003 ▶); Bruns et al. (1990 ▶).

Experimental

Crystal data

C14H16N2O2S

M = 276.35

Monoclinic,

a = 8.606 (2) Å

b = 7.5193 (19) Å

c = 21.297 (5) Å

β = 100.599 (5)°

V = 1354.7 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 291 (2) K

0.45 × 0.35 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.908, T max = 0.937

9834 measured reflections

2514 independent reflections

1503 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.142

S = 0.99

2514 reflections

175 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 1998 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801828X/bt2721sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801828X/bt2721Isup2.hkl

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

C14H16N2O2S	F000 = 584
Mr = 276.35	Dx = 1.355 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P2yn	Cell parameters from 670 reflections
a = 8.606 (2) Å	θ = 2.0–28.5º
b = 7.5193 (19) Å	µ = 0.24 mm−1
c = 21.297 (5) Å	T = 291 (2) K
β = 100.599 (5)º	Block, yellow
V = 1354.7 (6) Å3	0.45 × 0.35 × 0.28 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2514 independent reflections
Radiation source: fine-focus sealed tube	1503 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.051
T = 291(2) K	θmax = 25.5º
ψ and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.908, Tmax = 0.937	k = −9→9
9834 measured reflections	l = −25→23

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)] = 0.053	H-atom parameters constrained
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0749P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
2514 reflections	Δρmax = 0.25 e Å−3
175 parameters	Δρmin = −0.18 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
N1	0.2740 (3)	0.5092 (4)	0.74695 (12)	0.0593 (8)
H1A	0.2056	0.5582	0.7662	0.071*
H1B	0.2436	0.4570	0.7109	0.071*
N2	0.4683 (3)	0.6863 (3)	0.93475 (11)	0.0480 (7)
H2	0.5646	0.6512	0.9455	0.058*
O1	0.2675 (3)	0.7169 (3)	0.85124 (9)	0.0630 (7)
O2	0.6570 (3)	0.7367 (3)	1.04138 (10)	0.0676 (7)
S1	0.56490 (10)	0.41424 (12)	0.73395 (4)	0.0535 (3)
C2	0.4302 (3)	0.5144 (4)	0.77352 (13)	0.0420 (7)
C3	0.5040 (3)	0.5902 (4)	0.83034 (12)	0.0377 (7)
C4	0.6745 (3)	0.5669 (4)	0.84070 (13)	0.0398 (7)
C5	0.7229 (3)	0.4775 (4)	0.79298 (15)	0.0467 (7)
C6	0.4057 (3)	0.6700 (4)	0.87196 (14)	0.0420 (7)
C7	0.3992 (4)	0.7521 (4)	0.98507 (14)	0.0473 (8)
C8	0.2397 (4)	0.7879 (4)	0.98133 (16)	0.0627 (9)
H8	0.1694	0.7726	0.9430	0.075*
C9	0.1854 (5)	0.8470 (5)	1.0354 (2)	0.0760 (11)
H9	0.0784	0.8705	1.0332	0.091*
C10	0.2894 (6)	0.8706 (5)	1.09189 (19)	0.0783 (12)
H10	0.2519	0.9096	1.1278	0.094*
C11	0.4478 (5)	0.8375 (4)	1.09617 (16)	0.0681 (11)
H11	0.5174	0.8549	1.1346	0.082*
C12	0.5028 (4)	0.7782 (4)	1.04318 (14)	0.0528 (8)
C13	0.7904 (4)	0.6333 (4)	0.89802 (14)	0.0574 (9)
H13A	0.7849	0.5590	0.9342	0.086*
H13B	0.7642	0.7534	0.9074	0.086*
H13C	0.8955	0.6298	0.8889	0.086*
C14	0.8866 (4)	0.4251 (5)	0.78467 (17)	0.0650 (9)
H14A	0.9630	0.4970	0.8119	0.097*
H14B	0.8970	0.4428	0.7410	0.097*
H14C	0.9043	0.3021	0.7958	0.097*
C15	0.7716 (5)	0.7639 (6)	1.09758 (16)	0.0876 (13)
H15A	0.7754	0.8879	1.1086	0.131*
H15B	0.8733	0.7265	1.0902	0.131*
H15C	0.7435	0.6959	1.1320	0.131*

	U11	U22	U33	U12	U13	U23
N1	0.0488 (17)	0.082 (2)	0.0435 (15)	−0.0024 (14)	−0.0015 (13)	−0.0087 (14)
N2	0.0424 (14)	0.0643 (17)	0.0367 (14)	0.0069 (12)	0.0056 (12)	−0.0021 (12)
O1	0.0517 (14)	0.0900 (18)	0.0449 (13)	0.0223 (12)	0.0019 (11)	0.0006 (12)
O2	0.0649 (16)	0.0908 (18)	0.0437 (13)	−0.0020 (14)	0.0012 (12)	−0.0051 (12)
S1	0.0587 (6)	0.0575 (5)	0.0451 (5)	−0.0032 (4)	0.0117 (4)	−0.0088 (4)
C2	0.0434 (17)	0.0445 (16)	0.0374 (16)	−0.0041 (14)	0.0055 (14)	0.0028 (13)
C3	0.0402 (17)	0.0392 (15)	0.0327 (15)	0.0016 (13)	0.0043 (13)	0.0021 (13)
C4	0.0418 (17)	0.0356 (15)	0.0410 (17)	−0.0004 (13)	0.0051 (13)	0.0033 (13)
C5	0.0457 (18)	0.0442 (17)	0.0508 (18)	0.0008 (14)	0.0106 (15)	0.0013 (14)
C6	0.0418 (18)	0.0429 (17)	0.0395 (17)	0.0021 (14)	0.0031 (14)	0.0067 (13)
C7	0.058 (2)	0.0443 (18)	0.0433 (18)	0.0022 (15)	0.0187 (16)	0.0033 (14)
C8	0.067 (2)	0.070 (2)	0.055 (2)	0.0124 (18)	0.0222 (18)	0.0090 (18)
C9	0.083 (3)	0.075 (3)	0.081 (3)	0.024 (2)	0.044 (2)	0.020 (2)
C10	0.126 (4)	0.061 (2)	0.060 (3)	0.019 (2)	0.046 (3)	0.0082 (19)
C11	0.109 (3)	0.055 (2)	0.044 (2)	0.002 (2)	0.023 (2)	0.0019 (16)
C12	0.075 (2)	0.0466 (18)	0.0370 (18)	−0.0016 (17)	0.0123 (17)	0.0028 (14)
C13	0.0458 (19)	0.068 (2)	0.055 (2)	0.0007 (16)	0.0024 (16)	−0.0063 (17)
C14	0.056 (2)	0.066 (2)	0.075 (2)	0.0058 (18)	0.0185 (19)	−0.0091 (19)
C15	0.088 (3)	0.123 (3)	0.044 (2)	−0.026 (3)	−0.010 (2)	0.007 (2)

N1—C2	1.360 (3)	C7—C8	1.387 (5)
N1—H1A	0.8600	C8—C9	1.392 (5)
N1—H1B	0.8600	C8—H8	0.9300
N2—C6	1.352 (3)	C9—C10	1.373 (5)
N2—C7	1.407 (4)	C9—H9	0.9300
N2—H2	0.8600	C10—C11	1.373 (5)
O1—C6	1.241 (3)	C10—H10	0.9300
O2—C12	1.370 (4)	C11—C12	1.376 (4)
O2—C15	1.419 (4)	C11—H11	0.9300
S1—C2	1.727 (3)	C13—H13A	0.9600
S1—C5	1.740 (3)	C13—H13B	0.9600
C2—C3	1.382 (4)	C13—H13C	0.9600
C3—C4	1.454 (4)	C14—H14A	0.9600
C3—C6	1.462 (4)	C14—H14B	0.9600
C4—C5	1.347 (4)	C14—H14C	0.9600
C4—C13	1.512 (4)	C15—H15A	0.9600
C5—C14	1.504 (4)	C15—H15B	0.9600
C7—C12	1.399 (4)	C15—H15C	0.9600
C2—N1—H1A	120.0	C8—C9—H9	119.9
C2—N1—H1B	120.0	C10—C9—H9	119.9
H1A—N1—H1B	120.0	C11—C10—C9	120.9 (4)
C6—N2—C7	129.6 (3)	C11—C10—H10	119.5
C6—N2—H2	115.2	C9—C10—H10	119.5
C7—N2—H2	115.2	C10—C11—C12	119.5 (4)
C12—O2—C15	118.0 (3)	C10—C11—H11	120.3
C2—S1—C5	91.95 (14)	C12—C11—H11	120.3
N1—C2—C3	129.5 (3)	O2—C12—C11	125.3 (3)
N1—C2—S1	119.1 (2)	O2—C12—C7	114.0 (3)
C3—C2—S1	111.4 (2)	C11—C12—C7	120.8 (3)
C2—C3—C4	111.8 (3)	C4—C13—H13A	109.5
C2—C3—C6	118.4 (2)	C4—C13—H13B	109.5
C4—C3—C6	129.6 (2)	H13A—C13—H13B	109.5
C5—C4—C3	112.9 (3)	C4—C13—H13C	109.5
C5—C4—C13	121.6 (3)	H13A—C13—H13C	109.5
C3—C4—C13	125.4 (3)	H13B—C13—H13C	109.5
C4—C5—C14	130.2 (3)	C5—C14—H14A	109.5
C4—C5—S1	111.9 (2)	C5—C14—H14B	109.5
C14—C5—S1	117.9 (2)	H14A—C14—H14B	109.5
O1—C6—N2	120.5 (3)	C5—C14—H14C	109.5
O1—C6—C3	121.6 (3)	H14A—C14—H14C	109.5
N2—C6—C3	117.9 (2)	H14B—C14—H14C	109.5
C12—C7—N2	115.7 (3)	O2—C15—H15A	109.5
C12—C7—C8	119.1 (3)	O2—C15—H15B	109.5
N2—C7—C8	125.2 (3)	H15A—C15—H15B	109.5
C9—C8—C7	119.6 (4)	O2—C15—H15C	109.5
C9—C8—H8	120.2	H15A—C15—H15C	109.5
C7—C8—H8	120.2	H15B—C15—H15C	109.5
C8—C9—C10	120.2 (4)
C5—S1—C2—N1	179.1 (2)	C4—C3—C6—O1	163.3 (3)
C5—S1—C2—C3	−1.1 (2)	C2—C3—C6—N2	157.1 (3)
N1—C2—C3—C4	−179.5 (3)	C4—C3—C6—N2	−18.8 (4)
S1—C2—C3—C4	0.8 (3)	C6—N2—C7—C12	−170.1 (3)
N1—C2—C3—C6	3.9 (5)	C6—N2—C7—C8	11.3 (5)
S1—C2—C3—C6	−175.8 (2)	C12—C7—C8—C9	−0.7 (5)
C2—C3—C4—C5	0.1 (3)	N2—C7—C8—C9	177.8 (3)
C6—C3—C4—C5	176.3 (3)	C7—C8—C9—C10	0.4 (5)
C2—C3—C4—C13	−179.9 (3)	C8—C9—C10—C11	0.3 (6)
C6—C3—C4—C13	−3.8 (5)	C9—C10—C11—C12	−0.6 (5)
C3—C4—C5—C14	−179.9 (3)	C15—O2—C12—C11	−3.0 (5)
C13—C4—C5—C14	0.1 (5)	C15—O2—C12—C7	178.2 (3)
C3—C4—C5—S1	−1.0 (3)	C10—C11—C12—O2	−178.6 (3)
C13—C4—C5—S1	179.1 (2)	C10—C11—C12—C7	0.3 (5)
C2—S1—C5—C4	1.2 (2)	N2—C7—C12—O2	0.7 (4)
C2—S1—C5—C14	−179.7 (3)	C8—C7—C12—O2	179.4 (3)
C7—N2—C6—O1	0.1 (5)	N2—C7—C12—C11	−178.3 (3)
C7—N2—C6—C3	−177.8 (3)	C8—C7—C12—C11	0.4 (5)
C2—C3—C6—O1	−20.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	2.15	2.724 (3)	124
N1—H1B···O1i	0.86	2.23	3.009 (4)	151
N2—H2···O2	0.86	2.15	2.565 (3)	109
C8—H8···O1	0.93	2.30	2.874 (4)	119

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.86	2.15	2.724 (3)	124
N1—H1B⋯O1i	0.86	2.23	3.009 (4)	151
N2—H2⋯O2	0.86	2.15	2.565 (3)	109
C8—H8⋯O1	0.93	2.30	2.874 (4)	119

Symmetry code: (i) .