N-(4-Hydroxy-phen-yl)-2-(1,1,3-trioxo-2,3-di-hydro-1,2-benzothia-zol-2-yl)-acet-amide.

In the title compound, C(15)H(12)N(2)O(5)S, the benzisothia-zole group is approximately planar (r.m.s. deviation excluding H atoms and the two O atoms bonded to S = 0.023 Å). The dihedral angle between the benzisothia-zole ring and the terminal phenol ring is 84.9 (1)°. In the crystal, mol-ecules are joined by N-H⋯O and O-H⋯O hydrogen bonds, and π-stacking inter-actions are observed between alternating phenol and benzisothia-zole rings [centroid-centroid distances = 3.929 (3) and 3.943 (3) Å].

Related literature

For background literature related to analgesics, see: Slattery et al. (1996 ▶); McGoldrick & Bailie (1997 ▶); Watkins et al. (2006 ▶). For the synthesis and biological activity of the title compound, see: Vaccarino et al. (2007 ▶); González-Martin et al. (1998 ▶); Bazan & Alvarez-Builla (1996a ▶,b ▶). For related structures, see: Arshad et al. (2009 ▶); Siddiqui et al. (2008 ▶; 2007 ▶).

Experimental

Crystal data

C15H12N2O5S

M = 332.33

Orthorhombic,

a = 16.3588 (10) Å

b = 9.6451 (6) Å

c = 9.9603 (6) Å

V = 1571.56 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 230 K

0.60 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1K CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.832, T max = 0.954

19429 measured reflections

3580 independent reflections

3283 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.084

S = 1.07

3580 reflections

257 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.38 e Å−3

Absolute structure: Flack (1983 ▶), 1681 Friedel pairs

Flack parameter: 0.02 (8)

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 datablocks I, global. DOI: 10.1107/S1600536809023022/bi2377sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023022/bi2377Isup2.hkl

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

Enhanced figure: interactive version of Fig. 1

Enhanced figure: interactive version of Fig. 2

C15H12N2O5S	F(000) = 688
Mr = 332.33	Dx = 1.405 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 17706 reflections
a = 16.3588 (10) Å	θ = 2.5–30.5°
b = 9.6451 (6) Å	µ = 0.23 mm−1
c = 9.9603 (6) Å	T = 230 K
V = 1571.56 (17) Å3	Needle, colourless
Z = 4	0.60 × 0.20 × 0.20 mm

Bruker SMART 1K CCD diffractometer	3580 independent reflections
Radiation source: fine-focus sealed tube	3283 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −21→21
Tmin = 0.832, Tmax = 0.954	k = −12→12
19429 measured reflections	l = −12→12

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.039	w = 1/[σ2(Fo2) + (0.0183P)2 + 1.0724P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.084	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.28 e Å−3
3580 reflections	Δρmin = −0.38 e Å−3
257 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.0063 (8)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1681 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.02 (8)

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	0.11997 (4)	0.20573 (6)	0.93772 (6)	0.03830 (15)
O1	0.10058 (12)	0.3352 (2)	1.0007 (2)	0.0534 (5)
N2	0.09100 (11)	0.0757 (2)	1.0375 (2)	0.0339 (4)
O2	0.08966 (13)	0.1841 (2)	0.80485 (18)	0.0554 (5)
C3	0.15368 (14)	0.0026 (2)	1.0986 (2)	0.0320 (5)
O3	0.14167 (11)	−0.0882 (2)	1.17895 (19)	0.0451 (4)
C4	0.31014 (15)	0.0065 (3)	1.0784 (3)	0.0467 (6)
H4	0.3137 (16)	−0.067 (3)	1.135 (3)	0.034 (7)*
C4A	0.23289 (14)	0.0552 (3)	1.0467 (2)	0.0353 (5)
C5	0.37621 (17)	0.0677 (4)	1.0128 (4)	0.0608 (9)
H5	0.430 (2)	0.035 (4)	1.032 (4)	0.081 (11)*
C6	0.36573 (17)	0.1721 (4)	0.9215 (4)	0.0640 (9)
H6	0.4123 (19)	0.209 (3)	0.873 (4)	0.065 (9)*
C7A	0.22384 (13)	0.1609 (3)	0.9562 (3)	0.0398 (5)
C7	0.2887 (2)	0.2225 (3)	0.8913 (3)	0.0561 (8)
H7	0.283 (2)	0.295 (3)	0.830 (3)	0.058 (9)*
C8	0.00639 (14)	0.0545 (3)	1.0733 (2)	0.0346 (5)
H8B	−0.0203 (16)	0.141 (3)	1.072 (3)	0.038 (7)*
H8A	0.0067 (16)	0.018 (3)	1.162 (3)	0.035 (7)*
C9	−0.03588 (12)	−0.0469 (2)	0.9791 (2)	0.0298 (4)
O9	0.00080 (9)	−0.11209 (18)	0.89225 (16)	0.0379 (4)
N10	−0.11625 (11)	−0.0573 (2)	1.0033 (2)	0.0331 (4)
H10	−0.1339 (17)	−0.008 (3)	1.070 (3)	0.045 (8)*
C11	−0.17479 (12)	−0.1418 (2)	0.9368 (2)	0.0295 (4)
C12	−0.25630 (14)	−0.1228 (3)	0.9725 (3)	0.0391 (6)
H12	−0.2690 (17)	−0.049 (3)	1.033 (3)	0.047 (8)*
C13	−0.31719 (13)	−0.2010 (3)	0.9129 (3)	0.0407 (6)
H13	−0.3736 (19)	−0.187 (3)	0.933 (4)	0.066 (9)*
C14	−0.29711 (13)	−0.2994 (2)	0.8175 (2)	0.0320 (5)
O14	−0.35473 (10)	−0.3808 (2)	0.75619 (19)	0.0442 (5)
H14	−0.397 (2)	−0.378 (3)	0.802 (4)	0.060 (10)*
C15	−0.21627 (14)	−0.3179 (3)	0.7811 (2)	0.0341 (5)
H15	−0.2007 (16)	−0.386 (3)	0.716 (3)	0.040 (7)*
C16	−0.15511 (13)	−0.2396 (3)	0.8404 (2)	0.0320 (5)
H16	−0.1000 (17)	−0.255 (3)	0.814 (3)	0.041 (7)*

	U11	U22	U33	U12	U13	U23
S1	0.0371 (3)	0.0407 (3)	0.0371 (3)	−0.0060 (2)	−0.0064 (3)	0.0063 (3)
O1	0.0547 (11)	0.0422 (10)	0.0633 (12)	0.0011 (9)	−0.0100 (10)	0.0011 (9)
N2	0.0253 (9)	0.0422 (11)	0.0343 (10)	−0.0052 (8)	−0.0035 (7)	0.0048 (9)
O2	0.0640 (12)	0.0651 (13)	0.0371 (10)	−0.0036 (11)	−0.0141 (9)	0.0105 (9)
C3	0.0288 (11)	0.0366 (12)	0.0306 (11)	−0.0023 (9)	−0.0040 (9)	−0.0026 (10)
O3	0.0430 (10)	0.0481 (11)	0.0443 (10)	0.0011 (8)	−0.0010 (8)	0.0133 (9)
C4	0.0312 (12)	0.0594 (17)	0.0496 (15)	0.0012 (12)	−0.0040 (11)	−0.0117 (14)
C4A	0.0278 (11)	0.0438 (13)	0.0343 (11)	−0.0037 (10)	−0.0027 (10)	−0.0065 (10)
C5	0.0260 (13)	0.081 (2)	0.075 (2)	−0.0045 (14)	−0.0007 (13)	−0.0239 (19)
C6	0.0398 (14)	0.081 (2)	0.072 (2)	−0.0244 (15)	0.0125 (16)	−0.009 (2)
C7A	0.0312 (11)	0.0480 (13)	0.0401 (14)	−0.0085 (10)	0.0011 (10)	−0.0019 (11)
C7	0.0491 (16)	0.065 (2)	0.0547 (18)	−0.0222 (15)	0.0078 (13)	0.0049 (15)
C8	0.0256 (10)	0.0460 (14)	0.0323 (12)	−0.0015 (10)	−0.0004 (9)	−0.0030 (11)
C9	0.0246 (9)	0.0372 (11)	0.0275 (10)	−0.0002 (9)	−0.0012 (8)	0.0020 (9)
O9	0.0238 (7)	0.0520 (10)	0.0379 (9)	−0.0013 (7)	0.0043 (6)	−0.0089 (8)
N10	0.0249 (9)	0.0425 (11)	0.0319 (10)	−0.0037 (8)	0.0045 (8)	−0.0087 (9)
C11	0.0240 (8)	0.0352 (10)	0.0293 (9)	−0.0040 (8)	0.0016 (9)	−0.0002 (10)
C12	0.0276 (10)	0.0465 (14)	0.0432 (14)	−0.0007 (10)	0.0078 (10)	−0.0145 (11)
C13	0.0219 (10)	0.0511 (13)	0.0492 (16)	−0.0017 (10)	0.0059 (10)	−0.0093 (12)
C14	0.0254 (10)	0.0402 (12)	0.0304 (11)	−0.0067 (9)	0.0012 (9)	0.0024 (9)
O14	0.0284 (9)	0.0613 (12)	0.0427 (10)	−0.0135 (9)	0.0038 (8)	−0.0150 (9)
C15	0.0296 (11)	0.0408 (13)	0.0319 (11)	−0.0023 (10)	0.0053 (9)	−0.0044 (10)
C16	0.0216 (10)	0.0401 (12)	0.0343 (12)	−0.0010 (9)	0.0055 (9)	−0.0010 (10)

S1—O2	1.4286 (19)	C8—H8B	0.94 (3)
S1—O1	1.433 (2)	C8—H8A	0.95 (3)
S1—N2	1.668 (2)	C9—O9	1.226 (3)
S1—C7A	1.763 (2)	C9—N10	1.340 (3)
N2—C3	1.386 (3)	N10—C11	1.421 (3)
N2—C8	1.444 (3)	N10—H10	0.87 (3)
C3—O3	1.203 (3)	C11—C16	1.384 (3)
C3—C4A	1.484 (3)	C11—C12	1.392 (3)
C4—C4A	1.385 (3)	C12—C13	1.383 (3)
C4—C5	1.394 (4)	C12—H12	0.95 (3)
C4—H4	0.91 (3)	C13—C14	1.383 (3)
C4A—C7A	1.369 (4)	C13—H13	0.95 (3)
C5—C6	1.367 (5)	C14—O14	1.370 (3)
C5—H5	0.96 (4)	C14—C15	1.383 (3)
C6—C7	1.384 (4)	O14—H14	0.82 (3)
C6—H6	0.97 (3)	C15—C16	1.385 (3)
C7A—C7	1.377 (4)	C15—H15	0.96 (3)
C7—H7	0.93 (3)	C16—H16	0.95 (3)
C8—C9	1.522 (3)
O2—S1—O1	117.12 (13)	N2—C8—H8B	108.3 (16)
O2—S1—N2	110.07 (11)	C9—C8—H8B	110.3 (16)
O1—S1—N2	109.35 (12)	N2—C8—H8A	106.1 (16)
O2—S1—C7A	113.30 (13)	C9—C8—H8A	109.9 (16)
O1—S1—C7A	112.41 (12)	H8B—C8—H8A	110 (2)
N2—S1—C7A	91.57 (11)	O9—C9—N10	124.6 (2)
C3—N2—C8	121.9 (2)	O9—C9—C8	122.84 (19)
C3—N2—S1	115.73 (16)	N10—C9—C8	112.52 (19)
C8—N2—S1	121.75 (17)	C9—N10—C11	128.3 (2)
O3—C3—N2	122.8 (2)	C9—N10—H10	115.0 (19)
O3—C3—C4A	128.6 (2)	C11—N10—H10	116.6 (19)
N2—C3—C4A	108.6 (2)	C16—C11—C12	119.3 (2)
C4A—C4—C5	117.2 (3)	C16—C11—N10	123.88 (19)
C4A—C4—H4	117.7 (17)	C12—C11—N10	116.8 (2)
C5—C4—H4	125.0 (17)	C13—C12—C11	120.6 (2)
C7A—C4A—C4	120.1 (2)	C13—C12—H12	121.3 (17)
C7A—C4A—C3	112.9 (2)	C11—C12—H12	117.9 (17)
C4—C4A—C3	127.0 (2)	C12—C13—C14	119.9 (2)
C6—C5—C4	121.8 (3)	C12—C13—H13	122 (2)
C6—C5—H5	120 (2)	C14—C13—H13	118 (2)
C4—C5—H5	119 (2)	O14—C14—C15	117.9 (2)
C5—C6—C7	121.2 (3)	O14—C14—C13	122.4 (2)
C5—C6—H6	120.3 (19)	C15—C14—C13	119.7 (2)
C7—C6—H6	118 (2)	C14—O14—H14	108 (2)
C4A—C7A—C7	123.2 (2)	C14—C15—C16	120.6 (2)
C4A—C7A—S1	110.83 (17)	C14—C15—H15	121.2 (16)
C7—C7A—S1	126.0 (2)	C16—C15—H15	118.1 (16)
C7A—C7—C6	116.6 (3)	C11—C16—C15	119.9 (2)
C7A—C7—H7	123 (2)	C11—C16—H16	121.3 (16)
C6—C7—H7	120 (2)	C15—C16—H16	118.8 (16)
N2—C8—C9	111.95 (19)
O2—S1—N2—C3	121.36 (18)	O2—S1—C7A—C7	63.0 (3)
O1—S1—N2—C3	−108.64 (18)	O1—S1—C7A—C7	−72.6 (3)
C7A—S1—N2—C3	5.82 (19)	N2—S1—C7A—C7	175.7 (3)
O2—S1—N2—C8	−67.6 (2)	C4A—C7A—C7—C6	0.1 (5)
O1—S1—N2—C8	62.4 (2)	S1—C7A—C7—C6	179.4 (2)
C7A—S1—N2—C8	176.87 (19)	C5—C6—C7—C7A	−0.9 (5)
C8—N2—C3—O3	4.5 (4)	C3—N2—C8—C9	−96.0 (3)
S1—N2—C3—O3	175.5 (2)	S1—N2—C8—C9	93.5 (2)
C8—N2—C3—C4A	−176.0 (2)	N2—C8—C9—O9	6.7 (3)
S1—N2—C3—C4A	−5.0 (2)	N2—C8—C9—N10	−174.0 (2)
C5—C4—C4A—C7A	−1.1 (4)	O9—C9—N10—C11	−0.2 (4)
C5—C4—C4A—C3	177.2 (3)	C8—C9—N10—C11	−179.5 (2)
O3—C3—C4A—C7A	−179.5 (3)	C9—N10—C11—C16	6.3 (4)
N2—C3—C4A—C7A	1.0 (3)	C9—N10—C11—C12	−173.7 (2)
O3—C3—C4A—C4	2.1 (4)	C16—C11—C12—C13	0.3 (4)
N2—C3—C4A—C4	−177.4 (2)	N10—C11—C12—C13	−179.8 (2)
C4A—C4—C5—C6	0.3 (4)	C11—C12—C13—C14	0.3 (4)
C4—C5—C6—C7	0.7 (5)	C12—C13—C14—O14	179.3 (2)
C4—C4A—C7A—C7	0.9 (4)	C12—C13—C14—C15	−0.7 (4)
C3—C4A—C7A—C7	−177.6 (3)	O14—C14—C15—C16	−179.4 (2)
C4—C4A—C7A—S1	−178.4 (2)	C13—C14—C15—C16	0.6 (4)
C3—C4A—C7A—S1	3.1 (3)	C12—C11—C16—C15	−0.4 (3)
O2—S1—C7A—C4A	−117.6 (2)	N10—C11—C16—C15	179.7 (2)
O1—S1—C7A—C4A	106.8 (2)	C14—C15—C16—C11	−0.1 (4)
N2—S1—C7A—C4A	−5.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10···O14i	0.87 (3)	2.23 (3)	3.078 (3)	165 (3)
O14—H14···O9ii	0.82 (3)	1.91 (3)	2.725 (2)	173 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N10—H10⋯O14i	0.87 (3)	2.23 (3)	3.078 (3)	165 (3)
O14—H14⋯O9ii	0.82 (3)	1.91 (3)	2.725 (2)	173 (3)

Symmetry codes: (i) ; (ii) .