Literature DB >> 21580054

2-(6-Benzoyl-2-oxo-1,3-benzothia-zol-3-yl)acetic acid.

Abdullah Aydın, Mehmet Akkurt, Tijen Onkol, Orhan Büyükgüngör, M Fethi Sahin.   

Abstract

In the title compound, C(16)H(11)NO(4)S, the nine-membered fused ring is nearly planar, with maximum deviations from the mean plane of -0.022 (1) Å for the N atom and 0.011 (1) Å for the S atom, and makes a dihedral angle of 53.56 (7)° with the phenyl ring. The crystal structure is stabilized by O-H⋯O and C-H⋯O hydrogen-bonding inter-actions.

Entities:  

Year:  2009        PMID： 21580054      PMCID： PMC2980097          DOI： 10.1107/S160053680905329X

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the pharmacological effects of 2-benzoxazolinone/benzothia­zolinone derivatives, see: Ünlü et al. (2003 ▶); Petrov et al. (1994 ▶). For the quantum-chemical calculations, see: Pople & Beveridge (1970 ▶).

Experimental

Crystal data

C16H11NO4S M = 313.33 Orthorhombic, a = 11.4248 (3) Å b = 8.9155 (2) Å c = 27.6280 (8) Å V = 2814.13 (13) Å3 Z = 8 Mo Kα radiation μ = 0.25 mm−1 T = 296 K 0.59 × 0.38 × 0.17 mm

Data collection

Stoe IPDS 2 diffractometer Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.868, T max = 0.959 31503 measured reflections 3006 independent reflections 2363 reflections with I > 2σ(I) R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.033 wR(F 2) = 0.084 S = 1.04 3006 reflections 199 parameters H-atom parameters constrained Δρmax = 0.23 e Å−3 Δρmin = −0.22 e Å−3 Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); 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/S160053680905329X/hg2616sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053680905329X/hg2616Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H11NO4SF(000) = 1296
Mr = 313.33Dx = 1.479 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 31743 reflections
a = 11.4248 (3) Åθ = 1.5–27.3°
b = 8.9155 (2) ŵ = 0.25 mm−1
c = 27.6280 (8) ÅT = 296 K
V = 2814.13 (13) Å3Prismatic stick, colourless
Z = 80.59 × 0.38 × 0.17 mm
Stoe IPDS 2 diffractometer3006 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus2363 reflections with I > 2σ(I)
plane graphiteRint = 0.034
Detector resolution: 6.67 pixels mm-1θmax = 26.8°, θmin = 1.5°
ω scansh = −14→14
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)k = −11→11
Tmin = 0.868, Tmax = 0.959l = −34→34
31503 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0454P)2 + 0.2486P] where P = (Fo2 + 2Fc2)/3
3006 reflections(Δ/σ)max = 0.001
199 parametersΔρmax = 0.23 e Å−3
0 restraintsΔρmin = −0.22 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 on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.
xyzUiso*/Ueq
S10.57030 (3)0.23072 (5)0.52487 (1)0.0462 (1)
O10.92276 (8)0.45469 (15)0.63203 (5)0.0573 (4)
O20.35095 (10)0.25597 (15)0.49337 (5)0.0616 (4)
O30.22769 (11)0.33284 (18)0.61382 (5)0.0748 (5)
O40.11738 (11)0.5146 (2)0.58490 (7)0.1006 (7)
N10.41141 (9)0.41838 (15)0.55272 (5)0.0415 (4)
C10.85487 (12)0.61124 (17)0.69378 (6)0.0431 (5)
C20.78137 (14)0.6046 (2)0.73373 (6)0.0551 (6)
C30.80669 (18)0.6877 (3)0.77475 (7)0.0681 (7)
C40.90272 (18)0.7800 (3)0.77570 (8)0.0700 (8)
C50.97516 (18)0.7884 (2)0.73637 (8)0.0683 (7)
C60.95280 (14)0.7034 (2)0.69545 (7)0.0536 (6)
C70.83707 (12)0.51557 (17)0.65028 (6)0.0413 (5)
C80.71999 (11)0.49170 (17)0.62847 (5)0.0377 (4)
C90.71055 (11)0.38169 (17)0.59286 (5)0.0381 (4)
C100.60499 (11)0.36100 (17)0.56983 (5)0.0369 (4)
C110.50840 (11)0.45213 (17)0.58098 (5)0.0368 (4)
C120.51704 (12)0.56159 (18)0.61601 (6)0.0439 (5)
C130.62268 (12)0.58068 (18)0.63966 (6)0.0421 (5)
C140.42573 (13)0.30165 (19)0.52075 (6)0.0450 (5)
C150.30209 (11)0.5004 (2)0.55357 (6)0.0467 (5)
C160.21427 (12)0.4378 (2)0.58824 (6)0.0474 (5)
H20.715000.544200.732900.0660*
H30.758400.680900.801800.0820*
H40.918600.836900.803100.0840*
H4A0.068900.480700.603900.1510*
H51.039900.851600.737100.0820*
H61.003300.708100.669100.0640*
H90.774900.322900.584800.0460*
H120.453000.621500.623600.0530*
H130.629200.654000.663500.0500*
H15A0.268600.499900.521300.0560*
H15B0.318000.603900.562200.0560*
U11U22U33U12U13U23
S10.0364 (2)0.0550 (2)0.0471 (2)−0.0031 (2)0.0034 (2)−0.0099 (2)
O10.0299 (5)0.0725 (8)0.0696 (8)0.0023 (5)0.0037 (5)−0.0135 (7)
O20.0450 (6)0.0859 (9)0.0539 (7)−0.0120 (6)−0.0099 (5)−0.0088 (7)
O30.0626 (8)0.0835 (10)0.0784 (9)0.0153 (7)0.0236 (7)0.0317 (8)
O40.0414 (7)0.1141 (13)0.1464 (15)0.0268 (8)0.0339 (8)0.0644 (12)
N10.0271 (5)0.0520 (8)0.0453 (7)−0.0015 (5)0.0000 (5)0.0024 (6)
C10.0366 (7)0.0452 (9)0.0474 (8)0.0017 (6)−0.0073 (6)0.0022 (7)
C20.0472 (9)0.0682 (12)0.0500 (10)0.0000 (8)−0.0019 (7)0.0012 (9)
C30.0670 (11)0.0905 (15)0.0468 (10)0.0117 (11)−0.0050 (8)−0.0069 (10)
C40.0698 (12)0.0787 (15)0.0614 (12)0.0119 (10)−0.0237 (10)−0.0187 (11)
C50.0575 (10)0.0647 (13)0.0827 (15)−0.0073 (9)−0.0250 (10)−0.0094 (11)
C60.0413 (8)0.0592 (10)0.0604 (11)−0.0045 (7)−0.0089 (7)−0.0012 (9)
C70.0323 (7)0.0457 (9)0.0460 (8)−0.0017 (6)0.0014 (6)0.0029 (7)
C80.0308 (6)0.0420 (8)0.0402 (8)−0.0007 (6)0.0016 (5)0.0008 (7)
C90.0294 (6)0.0442 (8)0.0408 (8)0.0031 (6)0.0041 (5)0.0007 (7)
C100.0307 (6)0.0420 (8)0.0379 (7)−0.0018 (5)0.0048 (5)0.0011 (6)
C110.0269 (6)0.0431 (8)0.0405 (8)−0.0010 (5)0.0019 (5)0.0046 (7)
C120.0313 (7)0.0473 (9)0.0532 (9)0.0070 (6)0.0031 (6)−0.0044 (8)
C130.0365 (7)0.0422 (8)0.0476 (9)0.0014 (6)0.0014 (6)−0.0064 (7)
C140.0359 (7)0.0580 (10)0.0410 (8)−0.0095 (7)0.0021 (6)0.0037 (7)
C150.0290 (6)0.0546 (9)0.0564 (9)0.0015 (6)−0.0007 (6)0.0095 (8)
C160.0340 (7)0.0529 (10)0.0552 (10)0.0027 (6)0.0037 (6)0.0047 (8)
S1—C101.7462 (15)C8—C131.400 (2)
S1—C141.7723 (16)C8—C91.393 (2)
O1—C71.2277 (18)C9—C101.3760 (18)
O2—C141.212 (2)C10—C111.4046 (19)
O3—C161.183 (2)C11—C121.378 (2)
O4—C161.305 (2)C12—C131.383 (2)
O4—H4A0.8200C15—C161.495 (2)
N1—C141.375 (2)C2—H20.9300
N1—C151.4475 (18)C3—H30.9300
N1—C111.3885 (18)C4—H40.9300
C1—C61.389 (2)C5—H50.9300
C1—C71.488 (2)C6—H60.9300
C1—C21.388 (2)C9—H90.9300
C2—C31.385 (3)C12—H120.9300
C3—C41.372 (3)C13—H130.9300
C4—C51.368 (3)C15—H15A0.9700
C5—C61.385 (3)C15—H15B0.9700
C7—C81.4824 (19)
S1···N12.5858 (13)C15···O3viii3.416 (2)
S1···O2i3.2479 (12)C15···O2viii3.319 (2)
S1···C15ii3.5452 (17)C1···H132.7400
S1···O4iii3.3258 (17)C2···H132.6400
S1···H15Bii3.1000C4···H2xii2.9600
O1···O4iv2.6315 (18)C7···H4Aiv2.9600
O1···C13v3.381 (2)C8···H22.9200
O2···S1vi3.2479 (12)C12···H15B2.7400
O2···C15iii3.319 (2)C13···H9xii2.8900
O2···C9vi3.1233 (19)C13···H22.8000
O3···N12.7994 (18)C15···H122.8100
O3···C15iii3.416 (2)C16···H15Biii3.0800
O3···C3vii3.363 (3)H2···C82.9200
O4···C14viii3.152 (2)H2···C132.8000
O4···S1viii3.3258 (17)H2···H132.3700
O4···O1ix2.6315 (18)H2···C4v2.9600
O1···H92.4400H3···O3xi2.7000
O1···H13v2.8800H4···O1xiii2.7600
O1···H62.6500H4···O3xi2.8400
O1···H4Aiv1.8600H4A···O1ix1.8600
O1···H4x2.7600H4A···C7ix2.9600
O2···H15Aiii2.7700H6···O12.6500
O2···H15A2.4900H9···O12.4400
O2···H9vi2.4300H9···O2i2.4300
O3···H4vii2.8400H9···C13v2.8900
O3···H15Biii2.5400H12···C152.8100
O3···H12iii2.8100H12···H15B2.3000
O3···H3vii2.7000H12···O3viii2.8100
N1···S12.5858 (13)H13···C12.7400
N1···O32.7994 (18)H13···C22.6400
C2···C133.176 (2)H13···H22.3700
C3···O3xi3.363 (3)H13···O1xii2.8800
C9···C13v3.536 (2)H15A···O22.4900
C9···O2i3.1233 (19)H15A···O2viii2.7700
C13···C23.176 (2)H15B···C122.7400
C13···O1xii3.381 (2)H15B···H122.3000
C13···C9xii3.536 (2)H15B···S1ii3.1000
C14···O4iii3.152 (2)H15B···O3viii2.5400
C15···S1ii3.5452 (17)H15B···C16viii3.0800
C10—S1—C1491.14 (7)S1—C14—N1109.86 (11)
C16—O4—H4A110.00O2—C14—N1124.87 (14)
C11—N1—C14115.49 (12)S1—C14—O2125.26 (13)
C11—N1—C15124.75 (13)N1—C15—C16113.63 (14)
C14—N1—C15119.71 (12)O3—C16—C15126.24 (14)
C2—C1—C7122.36 (13)O4—C16—C15109.15 (15)
C6—C1—C7118.43 (14)O3—C16—O4124.57 (16)
C2—C1—C6119.09 (16)C1—C2—H2120.00
C1—C2—C3120.11 (16)C3—C2—H2120.00
C2—C3—C4120.25 (18)C2—C3—H3120.00
C3—C4—C5120.1 (2)C4—C3—H3120.00
C4—C5—C6120.46 (19)C3—C4—H4120.00
C1—C6—C5119.97 (17)C5—C4—H4120.00
O1—C7—C8119.28 (14)C4—C5—H5120.00
C1—C7—C8122.28 (12)C6—C5—H5120.00
O1—C7—C1118.44 (13)C1—C6—H6120.00
C7—C8—C9117.25 (12)C5—C6—H6120.00
C9—C8—C13119.55 (12)C8—C9—H9120.00
C7—C8—C13123.05 (13)C10—C9—H9120.00
C8—C9—C10119.26 (13)C11—C12—H12121.00
S1—C10—C11111.25 (10)C13—C12—H12121.00
C9—C10—C11120.64 (13)C8—C13—H13119.00
S1—C10—C9128.10 (11)C12—C13—H13119.00
N1—C11—C10112.23 (13)N1—C15—H15A109.00
N1—C11—C12127.27 (13)N1—C15—H15B109.00
C10—C11—C12120.49 (12)C16—C15—H15A109.00
C11—C12—C13118.78 (13)C16—C15—H15B109.00
C8—C13—C12121.25 (15)H15A—C15—H15B108.00
C14—S1—C10—C9−178.35 (15)C2—C3—C4—C5−1.1 (4)
C14—S1—C10—C110.72 (12)C3—C4—C5—C6−0.4 (3)
C10—S1—C14—N10.32 (12)C4—C5—C6—C11.4 (3)
C10—S1—C14—O2179.26 (16)O1—C7—C8—C13−165.40 (15)
C11—N1—C15—C16−92.11 (18)C1—C7—C8—C9−169.92 (14)
C15—N1—C14—O2−2.9 (2)C1—C7—C8—C1314.6 (2)
C11—N1—C14—S1−1.33 (17)O1—C7—C8—C910.1 (2)
C15—N1—C11—C123.7 (2)C9—C8—C13—C120.0 (2)
C14—N1—C11—C12−179.09 (15)C7—C8—C13—C12175.37 (15)
C11—N1—C14—O2179.73 (16)C7—C8—C9—C10−176.64 (13)
C14—N1—C11—C101.91 (19)C13—C8—C9—C10−1.0 (2)
C14—N1—C15—C1690.74 (18)C8—C9—C10—C111.8 (2)
C15—N1—C14—S1176.08 (11)C8—C9—C10—S1−179.27 (11)
C15—N1—C11—C10−175.35 (14)S1—C10—C11—C12179.35 (12)
C7—C1—C6—C5−176.84 (16)C9—C10—C11—N1177.56 (13)
C2—C1—C7—C843.9 (2)S1—C10—C11—N1−1.58 (16)
C2—C1—C6—C5−0.8 (2)C9—C10—C11—C12−1.5 (2)
C6—C1—C7—C8−140.18 (16)C10—C11—C12—C130.5 (2)
C6—C1—C7—O139.8 (2)N1—C11—C12—C13−178.44 (15)
C7—C1—C2—C3175.14 (17)C11—C12—C13—C80.3 (2)
C2—C1—C7—O1−136.10 (17)N1—C15—C16—O30.7 (3)
C6—C1—C2—C3−0.8 (3)N1—C15—C16—O4−177.21 (15)
C1—C2—C3—C41.7 (3)
D—H···AD—HH···AD···AD—H···A
O4—H4A···O1ix0.821.862.6315 (18)157
C9—H9···O2i0.932.433.1233 (19)131
C15—H15B···O3viii0.972.543.416 (2)150
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O4—H4A⋯O1i0.821.862.6315 (18)157
C9—H9⋯O2ii0.932.433.1233 (19)131
C15—H15B⋯O3iii0.972.543.416 (2)150

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

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1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

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Authors:  Serdar Unlü; Tijen Onkol; Yasemin Dündar; Berna Okçelik; Esra Küpeli; Erdem Yeşilada; Ningur Noyanalpan; M Fethi Sahin
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