2-[(2-Amino-phen-yl)sulfan-yl]-N-(4-meth-oxy-phen-yl)acetamide.

In the title compound, C(15)H(16)N(2)O(2)S, the dihedral angle between the 4-meth-oxy-aniline and 2-amino-benzene-thiole fragments is 35.60 (9)°. A short intra-molecular N-H⋯S contact leads to an S(5) ring. In the crystal, mol-ecules are consolidated in the form of polymeric chains along [010] as a result of N-H⋯O hydrogen bonds, which generate R(3) (2)(18) and R(4) (3)(22) loops. The polymeric chains are interlinked through C-H⋯O inter-action and complete R(2) (2)(8) ring motifs.

Related literature

For a related structure, see: Haisa et al. (1980 ▶). For hydrogen-bond motif notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H16N2O2S

M = 288.36

Monoclinic,

a = 12.9935 (16) Å

b = 4.7990 (4) Å

c = 23.433 (3) Å

β = 95.506 (7)°

V = 1454.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.25 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.965, T max = 0.975

11532 measured reflections

2845 independent reflections

1525 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.121

S = 1.01

2845 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812024178/hb6821sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024178/hb6821Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812024178/hb6821Isup3.cml

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

C15H16N2O2S	F(000) = 608
Mr = 288.36	Dx = 1.317 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1525 reflections
a = 12.9935 (16) Å	θ = 1.6–26.0°
b = 4.7990 (4) Å	µ = 0.23 mm−1
c = 23.433 (3) Å	T = 296 K
β = 95.506 (7)°	Needle, gray
V = 1454.4 (3) Å3	0.25 × 0.14 × 0.12 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2845 independent reflections
Radiation source: fine-focus sealed tube	1525 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
Detector resolution: 7.80 pixels mm-1	θmax = 26.0°, θmin = 1.6°
ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −5→5
Tmin = 0.965, Tmax = 0.975	l = −27→28
11532 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0435P)2 + 0.1361P] where P = (Fo2 + 2Fc2)/3
2845 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.67008 (6)	0.17005 (14)	0.17482 (3)	0.0513 (3)
O1	0.06467 (19)	0.2484 (5)	−0.05402 (11)	0.0942 (11)
O2	0.48924 (15)	0.0421 (3)	0.09749 (9)	0.0565 (8)
N1	0.43663 (19)	0.4757 (4)	0.07298 (10)	0.0480 (9)
N2	0.5848 (2)	0.4083 (5)	0.27906 (12)	0.0763 (12)
C1	0.3429 (2)	0.4077 (5)	0.03984 (12)	0.0423 (10)
C2	0.2538 (3)	0.5466 (6)	0.04982 (14)	0.0578 (11)
C3	0.1626 (3)	0.4868 (7)	0.01822 (16)	0.0750 (14)
C4	0.1593 (3)	0.2887 (7)	−0.02452 (14)	0.0590 (12)
C5	0.2468 (3)	0.1500 (6)	−0.03442 (13)	0.0569 (11)
C6	0.3386 (2)	0.2099 (6)	−0.00259 (12)	0.0496 (11)
C7	0.0533 (3)	0.0393 (9)	−0.09623 (17)	0.1020 (17)
C8	0.5023 (2)	0.2953 (5)	0.09956 (11)	0.0423 (10)
C9	0.5937 (2)	0.4227 (5)	0.13308 (13)	0.0606 (11)
C10	0.7332 (2)	0.4001 (5)	0.22519 (13)	0.0467 (11)
C11	0.6839 (3)	0.4890 (6)	0.27227 (14)	0.0520 (11)
C12	0.7355 (3)	0.6709 (7)	0.31078 (15)	0.0743 (14)
C13	0.8316 (3)	0.7639 (7)	0.30315 (18)	0.0838 (17)
C14	0.8816 (3)	0.6776 (7)	0.25769 (19)	0.0842 (16)
C15	0.8321 (3)	0.4935 (7)	0.21861 (16)	0.0654 (14)
H1	0.45235	0.64944	0.07614	0.0576*
H2	0.25569	0.68219	0.07826	0.0696*
H2A	0.55421	0.47092	0.30741	0.0916*
H2B	0.55300	0.29502	0.25497	0.0916*
H3	0.10255	0.58008	0.02558	0.0897*
H5	0.24472	0.01413	−0.06280	0.0680*
H6	0.39837	0.11528	−0.00991	0.0595*
H7A	0.07153	−0.13793	−0.07913	0.1529*
H7B	0.09784	0.07889	−0.12562	0.1529*
H7C	−0.01719	0.03419	−0.11275	0.1529*
H9A	0.57022	0.56384	0.15846	0.0724*
H9B	0.63654	0.51361	0.10692	0.0724*
H12	0.70365	0.73062	0.34250	0.0890*
H13	0.86413	0.88868	0.32937	0.1003*
H14	0.94784	0.74134	0.25299	0.1009*
H15	0.86569	0.43201	0.18764	0.0783*

	U11	U22	U33	U12	U13	U23
S1	0.0592 (5)	0.0369 (4)	0.0572 (5)	0.0064 (4)	0.0021 (4)	−0.0061 (4)
O1	0.0605 (17)	0.114 (2)	0.103 (2)	0.0024 (14)	−0.0178 (16)	−0.0410 (17)
O2	0.0715 (15)	0.0257 (10)	0.0700 (15)	−0.0040 (9)	−0.0054 (12)	−0.0028 (10)
N1	0.0592 (17)	0.0250 (12)	0.0578 (17)	−0.0080 (11)	−0.0050 (14)	−0.0015 (11)
N2	0.073 (2)	0.086 (2)	0.074 (2)	−0.0108 (16)	0.0276 (17)	−0.0247 (16)
C1	0.054 (2)	0.0314 (15)	0.0412 (18)	−0.0073 (14)	0.0034 (15)	0.0019 (13)
C2	0.065 (2)	0.0463 (18)	0.061 (2)	0.0043 (17)	0.0005 (19)	−0.0163 (16)
C3	0.056 (2)	0.080 (2)	0.088 (3)	0.0132 (19)	0.002 (2)	−0.027 (2)
C4	0.050 (2)	0.062 (2)	0.063 (2)	−0.0052 (17)	−0.0051 (18)	−0.0093 (18)
C5	0.062 (2)	0.0558 (19)	0.053 (2)	−0.0040 (17)	0.0063 (18)	−0.0160 (17)
C6	0.0485 (19)	0.0511 (17)	0.0498 (19)	−0.0019 (15)	0.0082 (16)	−0.0111 (16)
C7	0.091 (3)	0.112 (3)	0.097 (3)	−0.015 (3)	−0.022 (2)	−0.035 (3)
C8	0.055 (2)	0.0301 (15)	0.0423 (18)	−0.0035 (14)	0.0069 (15)	−0.0016 (14)
C9	0.073 (2)	0.0386 (17)	0.066 (2)	−0.0118 (15)	−0.0146 (19)	0.0056 (16)
C10	0.0467 (19)	0.0360 (16)	0.056 (2)	0.0069 (13)	−0.0020 (16)	−0.0011 (14)
C11	0.058 (2)	0.0446 (17)	0.052 (2)	0.0073 (16)	−0.0016 (18)	−0.0048 (16)
C12	0.086 (3)	0.074 (2)	0.061 (2)	−0.003 (2)	−0.002 (2)	−0.017 (2)
C13	0.084 (3)	0.072 (3)	0.089 (3)	0.001 (2)	−0.024 (3)	−0.021 (2)
C14	0.054 (2)	0.072 (2)	0.122 (4)	−0.010 (2)	−0.015 (2)	−0.006 (3)
C15	0.051 (2)	0.064 (2)	0.081 (3)	0.0049 (18)	0.005 (2)	−0.003 (2)

S1—C9	1.796 (3)	C10—C11	1.395 (4)
S1—C10	1.760 (3)	C11—C12	1.382 (5)
O1—C4	1.365 (5)	C12—C13	1.354 (5)
O1—C7	1.407 (5)	C13—C14	1.364 (6)
O2—C8	1.227 (3)	C14—C15	1.386 (5)
N1—C1	1.418 (4)	C2—H2	0.9300
N1—C8	1.328 (3)	C3—H3	0.9300
N2—C11	1.369 (5)	C5—H5	0.9300
N1—H1	0.8600	C6—H6	0.9300
N2—H2A	0.8600	C7—H7A	0.9600
N2—H2B	0.8600	C7—H7B	0.9600
C1—C2	1.375 (4)	C7—H7C	0.9600
C1—C6	1.372 (4)	C9—H9A	0.9700
C2—C3	1.366 (5)	C9—H9B	0.9700
C3—C4	1.379 (5)	C12—H12	0.9300
C4—C5	1.357 (5)	C13—H13	0.9300
C5—C6	1.375 (5)	C14—H14	0.9300
C8—C9	1.491 (4)	C15—H15	0.9300
C10—C15	1.384 (5)
C9—S1—C10	98.01 (12)	C13—C14—C15	119.0 (4)
C4—O1—C7	119.1 (3)	C10—C15—C14	120.7 (3)
C1—N1—C8	125.9 (2)	C1—C2—H2	120.00
C8—N1—H1	117.00	C3—C2—H2	120.00
C1—N1—H1	117.00	C2—C3—H3	120.00
C11—N2—H2A	120.00	C4—C3—H3	120.00
H2A—N2—H2B	120.00	C4—C5—H5	120.00
C11—N2—H2B	120.00	C6—C5—H5	120.00
N1—C1—C6	122.0 (2)	C1—C6—H6	120.00
N1—C1—C2	119.2 (2)	C5—C6—H6	120.00
C2—C1—C6	118.8 (3)	O1—C7—H7A	109.00
C1—C2—C3	120.4 (3)	O1—C7—H7B	109.00
C2—C3—C4	120.2 (3)	O1—C7—H7C	109.00
C3—C4—C5	119.6 (3)	H7A—C7—H7B	109.00
O1—C4—C3	115.4 (3)	H7A—C7—H7C	109.00
O1—C4—C5	124.9 (3)	H7B—C7—H7C	109.00
C4—C5—C6	120.2 (3)	S1—C9—H9A	109.00
C1—C6—C5	120.7 (3)	S1—C9—H9B	109.00
O2—C8—N1	123.2 (2)	C8—C9—H9A	109.00
O2—C8—C9	121.8 (2)	C8—C9—H9B	109.00
N1—C8—C9	115.0 (2)	H9A—C9—H9B	108.00
S1—C9—C8	112.38 (17)	C11—C12—H12	119.00
S1—C10—C15	120.4 (2)	C13—C12—H12	119.00
C11—C10—C15	119.4 (3)	C12—C13—H13	119.00
S1—C10—C11	120.2 (2)	C14—C13—H13	119.00
N2—C11—C12	120.4 (3)	C13—C14—H14	121.00
C10—C11—C12	118.6 (3)	C15—C14—H14	121.00
N2—C11—C10	120.9 (3)	C10—C15—H15	120.00
C11—C12—C13	121.2 (3)	C14—C15—H15	120.00
C12—C13—C14	121.2 (4)
C10—S1—C9—C8	−158.8 (2)	O1—C4—C5—C6	179.1 (3)
C9—S1—C10—C11	82.1 (2)	C3—C4—C5—C6	−1.0 (5)
C9—S1—C10—C15	−98.1 (3)	C4—C5—C6—C1	0.7 (5)
C7—O1—C4—C3	−176.6 (3)	O2—C8—C9—S1	−6.7 (3)
C7—O1—C4—C5	3.3 (5)	N1—C8—C9—S1	172.7 (2)
C8—N1—C1—C2	131.0 (3)	S1—C10—C11—N2	−2.5 (4)
C8—N1—C1—C6	−50.0 (4)	S1—C10—C11—C12	−179.6 (2)
C1—N1—C8—O2	1.2 (4)	C15—C10—C11—N2	177.8 (3)
C1—N1—C8—C9	−178.2 (2)	C15—C10—C11—C12	0.6 (4)
N1—C1—C2—C3	179.5 (3)	S1—C10—C15—C14	179.1 (3)
C6—C1—C2—C3	0.4 (4)	C11—C10—C15—C14	−1.1 (5)
N1—C1—C6—C5	−179.4 (3)	N2—C11—C12—C13	−176.7 (3)
C2—C1—C6—C5	−0.4 (4)	C10—C11—C12—C13	0.5 (5)
C1—C2—C3—C4	−0.8 (5)	C11—C12—C13—C14	−1.1 (6)
C2—C3—C4—O1	−179.0 (3)	C12—C13—C14—C15	0.6 (6)
C2—C3—C4—C5	1.1 (5)	C13—C14—C15—C10	0.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···S1	0.86	2.60	3.004 (3)	110
N1—H1···O2i	0.86	2.00	2.848 (3)	170
N2—H2A···O2ii	0.86	2.38	3.200 (3)	161
C3—H3···O1iii	0.93	2.47	3.393 (5)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯S1	0.86	2.60	3.004 (3)	110
N1—H1⋯O2i	0.86	2.00	2.848 (3)	170
N2—H2A⋯O2ii	0.86	2.38	3.200 (3)	161
C3—H3⋯O1iii	0.93	2.47	3.393 (5)	170

Symmetry codes: (i) ; (ii) ; (iii) .