3-Anilinothio-carbonyl-4-hydroxy-chromen-2-one.

The geometrical parameters of the title compound, C(16)H(11)NO(3)S, are in the usual ranges. The two aromatic residues are not coplanar and are twisted by a dihedral angle of 66.63 (6)°. The crystal structure is stabilized by N-H⋯O and O-H⋯S inter-actions.

Related literature

For literature on coumarins, see: Campbell (1959 ▶); Murray et al. (1982 ▶); Wolska et al. (1990 ▶); Harvey (1999 ▶); Matern et al. (1999 ▶); Yang et al. (1992 ▶); Tsai et al. (2000 ▶).

Experimental

Crystal data

C16H11NO3S

M = 297.33

Monoclinic,

a = 14.8059 (9) Å

b = 5.5245 (4) Å

c = 17.4438 (12) Å

β = 109.091 (7)°

V = 1348.34 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.30 × 0.24 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

Absorption correction: none

11450 measured reflections

4408 independent reflections

2320 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.134

S = 1.01

4408 reflections

235 parameters

All H-atom parameters refined

Δρmax = 0.24 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrysAlisPro (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlisPro; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXS86 (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: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809011246/jh2075sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011246/jh2075Isup2.hkl

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

C16H11NO3S	F(000) = 616
Mr = 297.33	Dx = 1.465 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.8059 (9) Å	Cell parameters from 2320 reflections
b = 5.5245 (4) Å	θ = 2.9–32.3°
c = 17.4438 (12) Å	µ = 0.25 mm−1
β = 109.091 (7)°	T = 293 K
V = 1348.34 (16) Å3	Rectangular, yellow
Z = 4	0.30 × 0.24 × 0.18 mm

Oxford Diffraction Xcalibur diffractometer	2320 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
graphite	θmax = 32.3°, θmin = 2.9°
ω–2θ scans	h = −20→21
11450 measured reflections	k = −8→5
4408 independent reflections	l = −25→26

Refinement on F2	0 constraints
Least-squares matrix: full	All H-atom parameters refined
R[F2 > 2σ(F2)] = 0.049	w = 1/[σ2(Fo2) + (0.0645P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.134	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.24 e Å−3
4408 reflections	Δρmin = −0.23 e Å−3
235 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0079 (18)

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.

	x	y	z	Uiso*/Ueq
H3	−0.2431 (14)	−0.089 (4)	−0.0463 (12)	0.058 (6)*
H1	−0.1035 (12)	0.344 (4)	0.1367 (11)	0.044 (5)*
H4	−0.1108 (14)	−0.346 (4)	−0.0190 (11)	0.053 (6)*
H2	−0.2420 (15)	0.255 (4)	0.0323 (13)	0.060 (6)*
H1A	0.2933 (15)	−0.272 (4)	0.2272 (13)	0.066 (7)*
H14	0.6547 (16)	−0.057 (4)	0.4609 (13)	0.074 (6)*
H12	0.4091 (17)	−0.402 (5)	0.3868 (13)	0.080 (8)*
H15	0.5906 (18)	0.239 (5)	0.3553 (16)	0.095 (9)*
H16	0.4290 (17)	0.200 (5)	0.2686 (16)	0.084 (8)*
H13	0.5615 (19)	−0.365 (5)	0.4674 (16)	0.099 (9)*
H3A	0.127 (2)	0.298 (5)	0.2783 (16)	0.102 (9)*
S1	0.24977 (3)	0.22219 (9)	0.33460 (3)	0.05005 (18)
C8	0.14300 (10)	−0.0442 (3)	0.20025 (9)	0.0319 (3)
O1	0.04858 (8)	−0.2950 (2)	0.08806 (7)	0.0400 (3)
O2	0.19660 (8)	−0.3959 (2)	0.14831 (7)	0.0497 (3)
C10	0.23535 (11)	0.0021 (3)	0.26441 (9)	0.0349 (4)
O3	0.06066 (9)	0.2954 (2)	0.23189 (8)	0.0470 (3)
C6	−0.02392 (11)	0.0583 (3)	0.12239 (9)	0.0329 (4)
C7	0.06394 (11)	0.1047 (3)	0.18839 (9)	0.0338 (4)
N1	0.30848 (10)	−0.1395 (3)	0.26561 (9)	0.0452 (4)
C5	−0.02859 (11)	−0.1432 (3)	0.07446 (9)	0.0333 (4)
C1	−0.10418 (12)	0.2061 (3)	0.10584 (12)	0.0423 (4)
C4	−0.10991 (12)	−0.2023 (4)	0.01022 (11)	0.0420 (4)
C9	0.13442 (12)	−0.2508 (3)	0.14694 (10)	0.0351 (4)
C11	0.40436 (12)	−0.1113 (4)	0.32054 (11)	0.0449 (4)
C2	−0.18535 (13)	0.1526 (4)	0.04245 (12)	0.0494 (5)
C3	−0.18805 (13)	−0.0511 (4)	−0.00491 (11)	0.0484 (5)
C16	0.45938 (15)	0.0776 (4)	0.31041 (15)	0.0619 (6)
C12	0.44115 (17)	−0.2784 (5)	0.37918 (17)	0.0725 (7)
C15	0.55294 (16)	0.0988 (5)	0.36243 (18)	0.0735 (7)
C14	0.58922 (15)	−0.0672 (5)	0.42249 (17)	0.0769 (8)
C13	0.53483 (19)	−0.2533 (5)	0.4308 (2)	0.0947 (11)

	U11	U22	U33	U12	U13	U23
S1	0.0422 (3)	0.0555 (3)	0.0476 (3)	−0.0063 (2)	0.00809 (19)	−0.0194 (2)
C8	0.0336 (8)	0.0328 (8)	0.0296 (8)	−0.0035 (7)	0.0105 (6)	−0.0054 (7)
O1	0.0368 (6)	0.0394 (7)	0.0388 (6)	0.0011 (5)	0.0053 (5)	−0.0093 (5)
O2	0.0435 (7)	0.0478 (8)	0.0498 (7)	0.0107 (6)	0.0044 (5)	−0.0145 (6)
C10	0.0351 (8)	0.0355 (9)	0.0351 (8)	−0.0044 (7)	0.0128 (6)	−0.0023 (7)
O3	0.0429 (7)	0.0470 (8)	0.0490 (7)	0.0045 (6)	0.0122 (6)	−0.0170 (6)
C6	0.0341 (8)	0.0331 (9)	0.0323 (8)	−0.0012 (7)	0.0119 (6)	0.0017 (7)
C7	0.0366 (8)	0.0337 (9)	0.0335 (8)	−0.0050 (7)	0.0149 (6)	−0.0015 (7)
N1	0.0335 (7)	0.0466 (9)	0.0490 (9)	−0.0002 (7)	0.0047 (6)	−0.0124 (8)
C5	0.0334 (8)	0.0325 (9)	0.0344 (8)	−0.0012 (7)	0.0113 (6)	0.0034 (7)
C1	0.0434 (10)	0.0391 (10)	0.0451 (10)	0.0058 (8)	0.0154 (8)	0.0049 (9)
C4	0.0413 (9)	0.0444 (11)	0.0373 (9)	−0.0086 (8)	0.0087 (7)	−0.0007 (8)
C9	0.0342 (8)	0.0365 (9)	0.0338 (8)	−0.0028 (7)	0.0099 (6)	−0.0032 (7)
C11	0.0334 (8)	0.0442 (11)	0.0521 (11)	−0.0010 (8)	0.0072 (8)	−0.0101 (9)
C2	0.0370 (9)	0.0545 (13)	0.0525 (11)	0.0086 (9)	0.0088 (8)	0.0123 (10)
C3	0.0347 (9)	0.0594 (13)	0.0439 (10)	−0.0065 (9)	0.0030 (8)	0.0094 (9)
C16	0.0458 (11)	0.0608 (14)	0.0740 (15)	−0.0072 (11)	0.0124 (10)	0.0046 (12)
C12	0.0509 (12)	0.0590 (15)	0.0860 (17)	−0.0148 (11)	−0.0073 (11)	0.0140 (13)
C15	0.0425 (11)	0.0662 (16)	0.110 (2)	−0.0167 (12)	0.0226 (12)	−0.0133 (15)
C14	0.0402 (11)	0.0640 (16)	0.103 (2)	−0.0036 (11)	−0.0091 (12)	−0.0183 (15)
C13	0.0616 (15)	0.0752 (18)	0.105 (2)	−0.0106 (14)	−0.0302 (15)	0.0220 (16)

S1—C10	1.6889 (17)	C1—H1	0.929 (19)
S1—H3A	1.81 (3)	C4—C3	1.381 (3)
C8—C7	1.390 (2)	C4—H4	0.94 (2)
C8—C9	1.452 (2)	C11—C12	1.353 (3)
C8—C10	1.479 (2)	C11—C16	1.370 (3)
O1—C9	1.3696 (19)	C2—C3	1.389 (3)
O1—C5	1.3737 (19)	C2—H2	0.98 (2)
O2—C9	1.215 (2)	C3—H3	0.919 (19)
C10—N1	1.330 (2)	C16—C15	1.391 (3)
O3—C7	1.308 (2)	C16—H16	0.99 (3)
O3—H3A	1.05 (3)	C12—C13	1.392 (3)
C6—C5	1.381 (2)	C12—H12	0.86 (3)
C6—C1	1.392 (2)	C15—C14	1.363 (4)
C6—C7	1.450 (2)	C15—H15	0.98 (3)
N1—C11	1.438 (2)	C14—C13	1.343 (4)
N1—H1A	0.97 (2)	C14—H14	0.98 (2)
C5—C4	1.389 (2)	C13—H13	0.88 (3)
C1—C2	1.373 (3)
C10—S1—H3A	84.7 (8)	O2—C9—O1	114.13 (14)
C7—C8—C9	118.50 (14)	O2—C9—C8	126.81 (15)
C7—C8—C10	122.40 (14)	O1—C9—C8	119.06 (14)
C9—C8—C10	119.10 (14)	C12—C11—C16	120.52 (19)
C9—O1—C5	122.43 (13)	C12—C11—N1	119.68 (18)
N1—C10—C8	117.17 (15)	C16—C11—N1	119.71 (18)
N1—C10—S1	120.18 (12)	C1—C2—C3	120.06 (18)
C8—C10—S1	122.65 (12)	C1—C2—H2	119.6 (13)
C7—O3—H3A	104.8 (15)	C3—C2—H2	120.3 (12)
C5—C6—C1	118.51 (15)	C4—C3—C2	121.14 (17)
C5—C6—C7	118.51 (14)	C4—C3—H3	119.0 (13)
C1—C6—C7	122.98 (16)	C2—C3—H3	119.9 (13)
O3—C7—C8	125.40 (14)	C11—C16—C15	119.2 (2)
O3—C7—C6	114.13 (14)	C11—C16—H16	118.0 (14)
C8—C7—C6	120.45 (15)	C15—C16—H16	122.7 (15)
C10—N1—C11	124.58 (16)	C11—C12—C13	119.4 (2)
C10—N1—H1A	115.4 (13)	C11—C12—H12	123.2 (15)
C11—N1—H1A	120.0 (13)	C13—C12—H12	117.4 (15)
O1—C5—C6	120.90 (14)	C14—C15—C16	120.2 (2)
O1—C5—C4	116.65 (15)	C14—C15—H15	121.9 (15)
C6—C5—C4	122.44 (15)	C16—C15—H15	117.9 (15)
C2—C1—C6	120.24 (19)	C13—C14—C15	119.9 (2)
C2—C1—H1	118.9 (11)	C13—C14—H14	117.6 (13)
C6—C1—H1	120.8 (11)	C15—C14—H14	122.5 (13)
C3—C4—C5	117.60 (18)	C14—C13—C12	120.8 (3)
C3—C4—H4	123.0 (12)	C14—C13—H13	118.1 (18)
C5—C4—H4	119.3 (12)	C12—C13—H13	120.9 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.96 (2)	1.77 (2)	2.5923 (19)	141 (2)
O3—H3A···S1	1.05 (2)	1.81 (3)	2.8163 (15)	159 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2	0.96 (2)	1.77 (2)	2.5923 (19)	141 (2)
O3—H3A⋯S1	1.05 (2)	1.81 (3)	2.8163 (15)	159 (2)