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

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ISSN: 2056-9890

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

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[Slattery, J. T., Nelson, S. D. & Thummel, K. E. (1996). Clin. Pharmacol. Ther. 60, 241-246.]); McGoldrick & Bailie (1997[McGoldrick, M. D. & Bailie, G. R. (1997). Ann. Pharmacother. 31, 221-227.]); Watkins et al. (2006[Watkins, P. B., Kaplowitz, N., Slattery, J. T., Colonese, C. R., Colucci, S. V., Stewart, P. W. & Harris, S. C. (2006). J. Am. Med. Assoc. 296, 87-90. ]). For the synthesis and biological activity of the title compound, see: Vaccarino et al. (2007[Vaccarino, A. L., Paul, D., Mukherjee, P. K., Rodriguez de Turco, E. B., Marcheselli, V. L., Xu, L., Trudell, M. L., Matia, M. P., Sunkel, C., Alvarez-Builla, J. & Bazan, N. G. (2007). Bioorg. Med. Chem. 15, 2206-2215.]); González-Martin et al. (1998[González-Martin, G., Lyndon, C. & Sunkel, C. (1998). Eur. J. Pharm. Biopharm. 46, 293-297.]); Bazan & Alvarez-Builla (1996a[Bazan, N. G. & Alvarez-Builla, J. (1996a). U. S. Patent 5 554 636.],b[Bazan, N. G. & Alvarez-Builla, J. (1996b). Chem. Abstr. 125, 266037k.]). For related structures, see: Arshad et al. (2009a[Arshad, M. N., Mubashar-ur-Rehman, H., Zia-ur-Rehman, M., Khan, I. U. & Shafiq, M. (2009a). Acta Cryst. E65, o1236.],b[Arshad, M. N., Mubashar-ur-Rehman, H., Zia-ur-Rehman, M., Khan, I. U. & Shafique, M. (2009b). Acta Cryst. E65, o1011.],c[Arshad, M. N., Tahir, M. N., Khan, I. U., Bilal, M. H. & Mubashar-ur-Rehman, H. (2009c). Acta Cryst. E65, o986.]); Siddiqui et al. (2008a[Siddiqui, W. A., Ahmad, S., Siddiqui, H. L., Hussain, R. A. & Parvez, M. (2008a). Acta Cryst. E64, o1897.],b[Siddiqui, W. A., Ahmad, S., Siddiqui, H. L. & Parvez, M. (2008b). Acta Cryst. E64, o724.]; 2007[Siddiqui, W. A., Ahmad, S., Khan, I. U., Siddiqui, H. L. & Parvez, M. (2007). Acta Cryst. E63, o4116.]).

[Scheme 1]

Experimental

Crystal data
  • C15H12N2O5S

  • Mr = 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[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.832, Tmax = 0.954

  • 19429 measured reflections

  • 3580 independent reflections

  • 3283 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.38 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1681 Friedel pairs

  • Flack parameter: 0.02 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

All H atoms were located in a difference density map and their positional parameters and Uiso included in the full-matrix least-squares refinement. Observed C—H bond lengths are in the range 0.91 (3)–0.97 (3) Å.

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
[Figure 1] Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] 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
C15H12N2O5SF(000) = 688
Mr = 332.33Dx = 1.405 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 17706 reflections
a = 16.3588 (10) Åθ = 2.5–30.5°
b = 9.6451 (6) ŵ = 0.23 mm1
c = 9.9603 (6) ÅT = 230 K
V = 1571.56 (17) Å3Needle, colourless
Z = 40.60 × 0.20 × 0.20 mm
Data collection top
Bruker SMART 1K CCD
diffractometer
3580 independent reflections
Radiation source: fine-focus sealed tube3283 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ϕ and ω scansθmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
h = 2121
Tmin = 0.832, Tmax = 0.954k = 1212
19429 measured reflectionsl = 1212
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH 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 = 1.07Δρmax = 0.28 e Å3
3580 reflectionsΔρmin = 0.38 e Å3
257 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0063 (8)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1681 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.02 (8)
Crystal data top
C15H12N2O5SV = 1571.56 (17) Å3
Mr = 332.33Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 16.3588 (10) ŵ = 0.23 mm1
b = 9.6451 (6) ÅT = 230 K
c = 9.9603 (6) Å0.60 × 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)
Tmin = 0.832, Tmax = 0.954Rint = 0.033
19429 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.084Δρmax = 0.28 e Å3
S = 1.07Δρmin = 0.38 e Å3
3580 reflectionsAbsolute structure: Flack (1983), 1681 Friedel pairs
257 parametersAbsolute 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
xyzUiso*/Ueq
S10.11997 (4)0.20573 (6)0.93772 (6)0.03830 (15)
O10.10058 (12)0.3352 (2)1.0007 (2)0.0534 (5)
N20.09100 (11)0.0757 (2)1.0375 (2)0.0339 (4)
O20.08966 (13)0.1841 (2)0.80485 (18)0.0554 (5)
C30.15368 (14)0.0026 (2)1.0986 (2)0.0320 (5)
O30.14167 (11)0.0882 (2)1.17895 (19)0.0451 (4)
C40.31014 (15)0.0065 (3)1.0784 (3)0.0467 (6)
H40.3137 (16)0.067 (3)1.135 (3)0.034 (7)*
C4A0.23289 (14)0.0552 (3)1.0467 (2)0.0353 (5)
C50.37621 (17)0.0677 (4)1.0128 (4)0.0608 (9)
H50.430 (2)0.035 (4)1.032 (4)0.081 (11)*
C60.36573 (17)0.1721 (4)0.9215 (4)0.0640 (9)
H60.4123 (19)0.209 (3)0.873 (4)0.065 (9)*
C7A0.22384 (13)0.1609 (3)0.9562 (3)0.0398 (5)
C70.2887 (2)0.2225 (3)0.8913 (3)0.0561 (8)
H70.283 (2)0.295 (3)0.830 (3)0.058 (9)*
C80.00639 (14)0.0545 (3)1.0733 (2)0.0346 (5)
H8B0.0203 (16)0.141 (3)1.072 (3)0.038 (7)*
H8A0.0067 (16)0.018 (3)1.162 (3)0.035 (7)*
C90.03588 (12)0.0469 (2)0.9791 (2)0.0298 (4)
O90.00080 (9)0.11209 (18)0.89225 (16)0.0379 (4)
N100.11625 (11)0.0573 (2)1.0033 (2)0.0331 (4)
H100.1339 (17)0.008 (3)1.070 (3)0.045 (8)*
C110.17479 (12)0.1418 (2)0.9368 (2)0.0295 (4)
C120.25630 (14)0.1228 (3)0.9725 (3)0.0391 (6)
H120.2690 (17)0.049 (3)1.033 (3)0.047 (8)*
C130.31719 (13)0.2010 (3)0.9129 (3)0.0407 (6)
H130.3736 (19)0.187 (3)0.933 (4)0.066 (9)*
C140.29711 (13)0.2994 (2)0.8175 (2)0.0320 (5)
O140.35473 (10)0.3808 (2)0.75619 (19)0.0442 (5)
H140.397 (2)0.378 (3)0.802 (4)0.060 (10)*
C150.21627 (14)0.3179 (3)0.7811 (2)0.0341 (5)
H150.2007 (16)0.386 (3)0.716 (3)0.040 (7)*
C160.15511 (13)0.2396 (3)0.8404 (2)0.0320 (5)
H160.1000 (17)0.255 (3)0.814 (3)0.041 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0371 (3)0.0407 (3)0.0371 (3)0.0060 (2)0.0064 (3)0.0063 (3)
O10.0547 (11)0.0422 (10)0.0633 (12)0.0011 (9)0.0100 (10)0.0011 (9)
N20.0253 (9)0.0422 (11)0.0343 (10)0.0052 (8)0.0035 (7)0.0048 (9)
O20.0640 (12)0.0651 (13)0.0371 (10)0.0036 (11)0.0141 (9)0.0105 (9)
C30.0288 (11)0.0366 (12)0.0306 (11)0.0023 (9)0.0040 (9)0.0026 (10)
O30.0430 (10)0.0481 (11)0.0443 (10)0.0011 (8)0.0010 (8)0.0133 (9)
C40.0312 (12)0.0594 (17)0.0496 (15)0.0012 (12)0.0040 (11)0.0117 (14)
C4A0.0278 (11)0.0438 (13)0.0343 (11)0.0037 (10)0.0027 (10)0.0065 (10)
C50.0260 (13)0.081 (2)0.075 (2)0.0045 (14)0.0007 (13)0.0239 (19)
C60.0398 (14)0.081 (2)0.072 (2)0.0244 (15)0.0125 (16)0.009 (2)
C7A0.0312 (11)0.0480 (13)0.0401 (14)0.0085 (10)0.0011 (10)0.0019 (11)
C70.0491 (16)0.065 (2)0.0547 (18)0.0222 (15)0.0078 (13)0.0049 (15)
C80.0256 (10)0.0460 (14)0.0323 (12)0.0015 (10)0.0004 (9)0.0030 (11)
C90.0246 (9)0.0372 (11)0.0275 (10)0.0002 (9)0.0012 (8)0.0020 (9)
O90.0238 (7)0.0520 (10)0.0379 (9)0.0013 (7)0.0043 (6)0.0089 (8)
N100.0249 (9)0.0425 (11)0.0319 (10)0.0037 (8)0.0045 (8)0.0087 (9)
C110.0240 (8)0.0352 (10)0.0293 (9)0.0040 (8)0.0016 (9)0.0002 (10)
C120.0276 (10)0.0465 (14)0.0432 (14)0.0007 (10)0.0078 (10)0.0145 (11)
C130.0219 (10)0.0511 (13)0.0492 (16)0.0017 (10)0.0059 (10)0.0093 (12)
C140.0254 (10)0.0402 (12)0.0304 (11)0.0067 (9)0.0012 (9)0.0024 (9)
O140.0284 (9)0.0613 (12)0.0427 (10)0.0135 (9)0.0038 (8)0.0150 (9)
C150.0296 (11)0.0408 (13)0.0319 (11)0.0023 (10)0.0053 (9)0.0044 (10)
C160.0216 (10)0.0401 (12)0.0343 (12)0.0010 (9)0.0055 (9)0.0010 (10)
Geometric parameters (Å, º) top
S1—O21.4286 (19)C8—H8B0.94 (3)
S1—O11.433 (2)C8—H8A0.95 (3)
S1—N21.668 (2)C9—O91.226 (3)
S1—C7A1.763 (2)C9—N101.340 (3)
N2—C31.386 (3)N10—C111.421 (3)
N2—C81.444 (3)N10—H100.87 (3)
C3—O31.203 (3)C11—C161.384 (3)
C3—C4A1.484 (3)C11—C121.392 (3)
C4—C4A1.385 (3)C12—C131.383 (3)
C4—C51.394 (4)C12—H120.95 (3)
C4—H40.91 (3)C13—C141.383 (3)
C4A—C7A1.369 (4)C13—H130.95 (3)
C5—C61.367 (5)C14—O141.370 (3)
C5—H50.96 (4)C14—C151.383 (3)
C6—C71.384 (4)O14—H140.82 (3)
C6—H60.97 (3)C15—C161.385 (3)
C7A—C71.377 (4)C15—H150.96 (3)
C7—H70.93 (3)C16—H160.95 (3)
C8—C91.522 (3)
O2—S1—O1117.12 (13)N2—C8—H8B108.3 (16)
O2—S1—N2110.07 (11)C9—C8—H8B110.3 (16)
O1—S1—N2109.35 (12)N2—C8—H8A106.1 (16)
O2—S1—C7A113.30 (13)C9—C8—H8A109.9 (16)
O1—S1—C7A112.41 (12)H8B—C8—H8A110 (2)
N2—S1—C7A91.57 (11)O9—C9—N10124.6 (2)
C3—N2—C8121.9 (2)O9—C9—C8122.84 (19)
C3—N2—S1115.73 (16)N10—C9—C8112.52 (19)
C8—N2—S1121.75 (17)C9—N10—C11128.3 (2)
O3—C3—N2122.8 (2)C9—N10—H10115.0 (19)
O3—C3—C4A128.6 (2)C11—N10—H10116.6 (19)
N2—C3—C4A108.6 (2)C16—C11—C12119.3 (2)
C4A—C4—C5117.2 (3)C16—C11—N10123.88 (19)
C4A—C4—H4117.7 (17)C12—C11—N10116.8 (2)
C5—C4—H4125.0 (17)C13—C12—C11120.6 (2)
C7A—C4A—C4120.1 (2)C13—C12—H12121.3 (17)
C7A—C4A—C3112.9 (2)C11—C12—H12117.9 (17)
C4—C4A—C3127.0 (2)C12—C13—C14119.9 (2)
C6—C5—C4121.8 (3)C12—C13—H13122 (2)
C6—C5—H5120 (2)C14—C13—H13118 (2)
C4—C5—H5119 (2)O14—C14—C15117.9 (2)
C5—C6—C7121.2 (3)O14—C14—C13122.4 (2)
C5—C6—H6120.3 (19)C15—C14—C13119.7 (2)
C7—C6—H6118 (2)C14—O14—H14108 (2)
C4A—C7A—C7123.2 (2)C14—C15—C16120.6 (2)
C4A—C7A—S1110.83 (17)C14—C15—H15121.2 (16)
C7—C7A—S1126.0 (2)C16—C15—H15118.1 (16)
C7A—C7—C6116.6 (3)C11—C16—C15119.9 (2)
C7A—C7—H7123 (2)C11—C16—H16121.3 (16)
C6—C7—H7120 (2)C15—C16—H16118.8 (16)
N2—C8—C9111.95 (19)
O2—S1—N2—C3121.36 (18)O2—S1—C7A—C763.0 (3)
O1—S1—N2—C3108.64 (18)O1—S1—C7A—C772.6 (3)
C7A—S1—N2—C35.82 (19)N2—S1—C7A—C7175.7 (3)
O2—S1—N2—C867.6 (2)C4A—C7A—C7—C60.1 (5)
O1—S1—N2—C862.4 (2)S1—C7A—C7—C6179.4 (2)
C7A—S1—N2—C8176.87 (19)C5—C6—C7—C7A0.9 (5)
C8—N2—C3—O34.5 (4)C3—N2—C8—C996.0 (3)
S1—N2—C3—O3175.5 (2)S1—N2—C8—C993.5 (2)
C8—N2—C3—C4A176.0 (2)N2—C8—C9—O96.7 (3)
S1—N2—C3—C4A5.0 (2)N2—C8—C9—N10174.0 (2)
C5—C4—C4A—C7A1.1 (4)O9—C9—N10—C110.2 (4)
C5—C4—C4A—C3177.2 (3)C8—C9—N10—C11179.5 (2)
O3—C3—C4A—C7A179.5 (3)C9—N10—C11—C166.3 (4)
N2—C3—C4A—C7A1.0 (3)C9—N10—C11—C12173.7 (2)
O3—C3—C4A—C42.1 (4)C16—C11—C12—C130.3 (4)
N2—C3—C4A—C4177.4 (2)N10—C11—C12—C13179.8 (2)
C4A—C4—C5—C60.3 (4)C11—C12—C13—C140.3 (4)
C4—C5—C6—C70.7 (5)C12—C13—C14—O14179.3 (2)
C4—C4A—C7A—C70.9 (4)C12—C13—C14—C150.7 (4)
C3—C4A—C7A—C7177.6 (3)O14—C14—C15—C16179.4 (2)
C4—C4A—C7A—S1178.4 (2)C13—C14—C15—C160.6 (4)
C3—C4A—C7A—S13.1 (3)C12—C11—C16—C150.4 (3)
O2—S1—C7A—C4A117.6 (2)N10—C11—C16—C15179.7 (2)
O1—S1—C7A—C4A106.8 (2)C14—C15—C16—C110.1 (4)
N2—S1—C7A—C4A5.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N10—H10···O14i0.87 (3)2.23 (3)3.078 (3)165 (3)
O14—H14···O9ii0.82 (3)1.91 (3)2.725 (2)173 (3)
Symmetry codes: (i) x1/2, y+1/2, z+1/2; (ii) x1/2, y1/2, z.

Experimental details

Crystal data
Chemical formulaC15H12N2O5S
Mr332.33
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)230
a, b, c (Å)16.3588 (10), 9.6451 (6), 9.9603 (6)
V3)1571.56 (17)
Z4
Radiation typeMo Kα
µ (mm1)0.23
Crystal size (mm)0.60 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART 1K CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2007)
Tmin, Tmax0.832, 0.954
No. of measured, independent and
observed [I > 2σ(I)] reflections
19429, 3580, 3283
Rint0.033
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.084, 1.07
No. of reflections3580
No. of parameters257
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.28, 0.38
Absolute structureFlack (1983), 1681 Friedel pairs
Absolute structure parameter0.02 (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···AD—HH···AD···AD—H···A
N10—H10···O14i0.87 (3)2.23 (3)3.078 (3)165 (3)
O14—H14···O9ii0.82 (3)1.91 (3)2.725 (2)173 (3)
Symmetry codes: (i) x1/2, y+1/2, z+1/2; (ii) x1/2, y1/2, z.
 

Acknowledgements

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

References

First citationArshad, 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
First citationArshad, M. N., Mubashar-ur-Rehman, H., Zia-ur-Rehman, M., Khan, I. U. & Shafique, M. (2009b). Acta Cryst. E65, o1011.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationArshad, M. N., Tahir, M. N., Khan, I. U., Bilal, M. H. & Mubashar-ur-Rehman, H. (2009c). Acta Cryst. E65, o986.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBazan, N. G. & Alvarez-Builla, J. (1996a). U. S. Patent 5 554 636.  Google Scholar
First citationBazan, N. G. & Alvarez-Builla, J. (1996b). Chem. Abstr. 125, 266037k.  Google Scholar
First citationBruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationGonzález-Martin, G., Lyndon, C. & Sunkel, C. (1998). Eur. J. Pharm. Biopharm. 46, 293-297.  Web of Science CrossRef PubMed Google Scholar
First citationMcGoldrick, M. D. & Bailie, G. R. (1997). Ann. Pharmacother. 31, 221–227.  CAS PubMed Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiddiqui, W. A., Ahmad, S., Khan, I. U., Siddiqui, H. L. & Parvez, M. (2007). Acta Cryst. E63, o4116.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSiddiqui, W. A., Ahmad, S., Siddiqui, H. L., Hussain, R. A. & Parvez, M. (2008a). Acta Cryst. E64, o1897.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSiddiqui, W. A., Ahmad, S., Siddiqui, H. L. & Parvez, M. (2008b). Acta Cryst. E64, o724.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSlattery, J. T., Nelson, S. D. & Thummel, K. E. (1996). Clin. Pharmacol. Ther. 60, 241–246.  CrossRef CAS PubMed Web of Science Google Scholar
First citationVaccarino, A. L., Paul, D., Mukherjee, P. K., Rodriguez de Turco, E. B., Marcheselli, V. L., Xu, L., Trudell, M. L., Matia, M. P., Sunkel, C., Alvarez-Builla, J. & Bazan, N. G. (2007). Bioorg. Med. Chem. 15, 2206–2215.  Web of Science CrossRef PubMed CAS Google Scholar
First citationWatkins, P. B., Kaplowitz, N., Slattery, J. T., Colonese, C. R., Colucci, S. V., Stewart, P. W. & Harris, S. C. (2006). J. Am. Med. Assoc. 296, 87–90.   Web of Science CrossRef CAS Google Scholar

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