N-(4-Hydroxy­phen­yl)-2-(1,1,3-trioxo-2,3-di­hydro-1,2-benzothia­zol-2-yl)­acet­amide

Verma, A.; Stevens, E.D.

doi:10.1107/S1600536809023022

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1667

doi:10.1107/S1600536809023022

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N-(4-Hydroxyphenyl)-2-(1,1,3-trioxo-2,3-dihydro-1,2-benzothiazol-2-yl)acetamide

Abha Verma ^a and Edwin D. Stevens ^a ^*

^aDepartment of Chemistry, University of New Orleans, New Orleans, LA 70148, USA
^*Correspondence e-mail: estevens@uno.edu

(Received 18 May 2009; accepted 15 June 2009; online 24 June 2009)

In the title compound, C₁₅H₁₂N₂O₅S, the benzisothiazole 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 benzisothiazole ring and the terminal phenol ring is 84.9 (1)°. In the crystal, molecules are joined by N—H⋯O and O—H⋯O hydrogen bonds, and π-stacking interactions are observed between alternating phenol and benzisothiazole 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. (2009a ,b ,c ); Siddiqui et al. (2008a ,b ; 2007 ).

Experimental

Crystal data

C₁₅H₁₂N₂O₅S
M_r = 332.33
Orthorhombic, P n a 2₁
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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.084
S = 1.07
3580 reflections
257 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.38 e Å⁻³
Absolute structure: Flack (1983 ), 1681 Friedel pairs
Flack parameter: 0.02 (8)

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) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809023022/bi2377sup1.cif

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

checkCIF report

Comment top

Analgesics currently in use have high incidence of adverse reactions and can cause potentially lethal effects like hepatotoxicity and nephrotoxicity (Slattery et al., 1996; McGoldrick & Bailie, 1997; Watkins et al., 2006). A series of compounds bearing the acetaminophen (Tylenol) fragment linked to different lipophilic heterocyclic moieties were synthesized with a view to modulate its pharmacokinetic profile (Bazan & Alvarez-Builla, 1996a,b6; Vaccarino et al., 2007). Of these new derivatives, the title compound (commonly called SCP-1) has a similar profile to that of acetaminophen but with shorter elimination half-life and clearance.

Related literature top

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. (2009a,b,c); Siddiqui et al. (2008a,b; 2007).

Experimental top

The title compound was synthesized following the procedure described by Vaccarino et al. (2007) and colourless needles suitable for X-ray analysis were obtained by recrystallization from an ethanol-water (8:1) mixture.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Perspective view of the contents of the unit cell showing the parallel stacking of the aromatic rings in layers perpendicular to the a axis.

N-(4-Hydroxyphenyl)-2-(1,1,3-trioxo-2,3-dihydro-1,2-benzothiazol- 2-yl)acetamide top

Crystal data top

C₁₅H₁₂N₂O₅S	F(000) = 688
M_r = 332.33	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0183P)² + 1.0724P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.084	(Δ/σ)_max < 0.001
S = 1.07	Δρ_max = 0.28 e Å⁻³
3580 reflections	Δρ_min = −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	Absolute structure parameter: 0.02 (8)

Crystal data top

C₁₅H₁₂N₂O₅S	V = 1571.56 (17) Å³
M_r = 332.33	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 16.3588 (10) Å	µ = 0.23 mm⁻¹
b = 9.6451 (6) Å	T = 230 K
c = 9.9603 (6) Å	0.60 × 0.20 × 0.20 mm

Data collection top

Bruker SMART 1K CCD diffractometer	3580 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	3283 reflections with I > 2σ(I)
T_min = 0.832, T_max = 0.954	R_int = 0.033
19429 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.084	Δρ_max = 0.28 e Å⁻³
S = 1.07	Δρ_min = −0.38 e Å⁻³
3580 reflections	Absolute structure: Flack (1983), 1681 Friedel pairs
257 parameters	Absolute structure parameter: 0.02 (8)
1 restraint

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x−1/2, y+1/2, z+1/2; (ii) x−1/2, −y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂N₂O₅S
M_r	332.33
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	230
a, b, c (Å)	16.3588 (10), 9.6451 (6), 9.9603 (6)
V (Å³)	1571.56 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.60 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART 1K CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.832, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	19429, 3580, 3283
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.084, 1.07
No. of reflections	3580
No. of parameters	257
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.38
Absolute structure	Flack (1983), 1681 Friedel pairs
Absolute structure parameter	0.02 (8)

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x−1/2, y+1/2, z+1/2; (ii) x−1/2, −y−1/2, z.

Acknowledgements

Helpful discussions with Professor M. L. Trudell, University of New Orleans, are gratefully acknowledged.

References

Arshad, M. N., Mubashar-ur-Rehman, H., Zia-ur-Rehman, M., Khan, I. U. & Shafiq, M. (2009a). Acta Cryst. E65, o1236. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Volume 65| Part 7| July 2009| Page o1667

doi:10.1107/S1600536809023022

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N-(4-Hy­droxy­phen­yl)-2-(1,1,3-trioxo-2,3-di­hydro-1,2-benzo­thia­zol-2-yl)­acet­amide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-(4-Hydroxyphenyl)-2-(1,1,3-trioxo-2,3-dihydro-1,2-benzothiazol-2-yl)acetamide