Literature DB >> 22058918

2-(1,3-Benzothia-zol-2-yl)-6-eth-oxy-phenol.

D Lakshmanan, R Madhan Raj, R Selvakumar, M Bakthadoss, S Murugavel.

Abstract

In the title compound, C(15)H(13)NO(2)S, the benzothia-zole unit is essentially planar [maximum deviation = -0.0099 (5) Å for the S atom] and is oriented at a dihedral angle of 4.8 (5)° with respect to the benzene ring. An intra-molecular O-H⋯N hydrogen bond generates an S(6) ring motif. The crystal packing is stabilized by C-H⋯π inter-actions.

Entities: CellLine Chemical Disease Species

Year: 2011 PMID： 22058918 PMCID： PMC3200763 DOI： 10.1107/S160053681103114X

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

Related literature

For background to the applications of benzothiazoles in the chemical industry, see: Bradshaw et al. (2002 ▶); Delmas et al. (2002 ▶); Hutchinson et al. (2002 ▶). For the pharmacological activity of benzothiazole derivatives, see: Repiĉ et al. (2001 ▶); Schwartz et al. (1992 ▶). For related structures, see: Baryala et al. (2010 ▶); Zhang et al. (2008 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H13NO2S M = 271.32 Monoclinic, a = 9.8739 (5) Å b = 9.6222 (4) Å c = 13.3644 (6) Å β = 95.269 (2)° V = 1264.37 (10) Å3 Z = 4 Mo Kα radiation μ = 0.25 mm−1 T = 293 K 0.24 × 0.22 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996) ▶ T min = 0.941, T max = 0.960 19076 measured reflections 5191 independent reflections 3449 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.125 S = 1.01 5191 reflections 173 parameters H-atom parameters constrained Δρmax = 0.36 e Å−3 Δρmin = −0.21 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia (1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681103114X/bt5597sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103114X/bt5597Isup2.hkl Supplementary material file. DOI: 10.1107/S160053681103114X/bt5597Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₅H₁₃NO₂S	F(000) = 568
M_r = 271.32	D_x = 1.425 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5191 reflections
a = 9.8739 (5) Å	θ = 2.5–34.1°
b = 9.6222 (4) Å	µ = 0.25 mm⁻¹
c = 13.3644 (6) Å	T = 293 K
β = 95.269 (2)°	Block, yellow
V = 1264.37 (10) Å³	0.24 × 0.22 × 0.16 mm
Z = 4

Bruker APEXII CCD diffractometer	5191 independent reflections
Radiation source: fine-focus sealed tube	3449 reflections with I > 2σ(I)
graphite	R_int = 0.023
Detector resolution: 10.0 pixels mm^-1	θ_max = 34.1°, θ_min = 2.5°
ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −15→9
T_min = 0.941, T_max = 0.960	l = −21→19
19076 measured reflections

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0658P)² + 0.1388P] where P = (F_o² + 2F_c²)/3
5191 reflections	(Δ/σ)_max < 0.001
173 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	U_iso*/U_eq
S1	0.05727 (3)	0.30307 (3)	0.19431 (2)	0.03712 (10)
N1	0.02751 (10)	0.27133 (10)	0.00112 (7)	0.0326 (2)
C8	−0.12040 (11)	0.11723 (12)	0.08584 (8)	0.0313 (2)
C13	−0.18273 (11)	0.06427 (12)	−0.00477 (8)	0.0312 (2)
O2	−0.33618 (10)	−0.08310 (10)	−0.09512 (6)	0.0439 (2)
O1	−0.15176 (10)	0.10695 (10)	−0.09587 (6)	0.0424 (2)
H1	−0.0923	0.1666	−0.0891	0.064*
C1	−0.01672 (11)	0.22478 (12)	0.08401 (8)	0.0309 (2)
C12	−0.28288 (12)	−0.03998 (12)	−0.00288 (8)	0.0332 (2)
C11	−0.31818 (13)	−0.09032 (13)	0.08807 (9)	0.0377 (3)
H11	−0.3841	−0.1591	0.0893	0.045*
C2	0.12562 (11)	0.37329 (12)	0.02054 (8)	0.0312 (2)
C7	0.15529 (12)	0.40571 (12)	0.12266 (8)	0.0328 (2)
C9	−0.15855 (13)	0.06359 (13)	0.17719 (9)	0.0393 (3)
H9	−0.1177	0.0977	0.2377	0.047*
C14	−0.43972 (13)	−0.18786 (12)	−0.09985 (10)	0.0378 (3)
H14A	−0.5186	−0.1550	−0.0686	0.045*
H14B	−0.4060	−0.2714	−0.0654	0.045*
C10	−0.25549 (14)	−0.03849 (14)	0.17758 (9)	0.0408 (3)
H10	−0.2794	−0.0733	0.2384	0.049*
C3	0.19474 (13)	0.44135 (13)	−0.05155 (9)	0.0389 (3)
H3	0.1766	0.4205	−0.1194	0.047*
C6	0.25186 (13)	0.50573 (13)	0.15417 (9)	0.0400 (3)
H6	0.2709	0.5271	0.2219	0.048*
C4	0.29027 (14)	0.53996 (14)	−0.02046 (10)	0.0444 (3)
H4	0.3370	0.5860	−0.0679	0.053*
C15	−0.47613 (16)	−0.21685 (16)	−0.20937 (11)	0.0508 (3)
H15A	−0.5093	−0.1333	−0.2424	0.076*
H15B	−0.5454	−0.2871	−0.2166	0.076*
H15C	−0.3970	−0.2487	−0.2392	0.076*
C5	0.31827 (14)	0.57200 (14)	0.08114 (11)	0.0451 (3)
H5	0.3831	0.6395	0.1001	0.054*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.04228 (17)	0.04402 (18)	0.02515 (13)	−0.00088 (12)	0.00359 (11)	−0.00212 (11)
N1	0.0336 (5)	0.0369 (5)	0.0273 (4)	−0.0006 (4)	0.0023 (4)	0.0005 (4)
C8	0.0331 (5)	0.0336 (5)	0.0274 (5)	0.0030 (4)	0.0044 (4)	0.0008 (4)
C13	0.0348 (5)	0.0321 (5)	0.0274 (5)	0.0033 (4)	0.0060 (4)	0.0013 (4)
O2	0.0518 (5)	0.0482 (5)	0.0319 (4)	−0.0162 (4)	0.0042 (4)	−0.0041 (4)
O1	0.0528 (5)	0.0484 (5)	0.0264 (4)	−0.0143 (4)	0.0059 (3)	0.0005 (3)
C1	0.0326 (5)	0.0340 (5)	0.0262 (5)	0.0046 (4)	0.0026 (4)	0.0001 (4)
C12	0.0358 (6)	0.0331 (5)	0.0311 (5)	0.0016 (4)	0.0056 (4)	−0.0016 (4)
C11	0.0400 (6)	0.0372 (6)	0.0371 (6)	−0.0022 (5)	0.0107 (5)	0.0011 (5)
C2	0.0326 (5)	0.0317 (5)	0.0289 (5)	0.0027 (4)	−0.0001 (4)	0.0002 (4)
C7	0.0349 (6)	0.0343 (5)	0.0288 (5)	0.0048 (4)	0.0013 (4)	−0.0011 (4)
C9	0.0448 (7)	0.0467 (7)	0.0267 (5)	−0.0009 (5)	0.0054 (5)	0.0013 (5)
C14	0.0345 (6)	0.0357 (6)	0.0435 (6)	−0.0020 (5)	0.0041 (5)	−0.0015 (5)
C10	0.0466 (7)	0.0464 (7)	0.0308 (5)	−0.0012 (6)	0.0107 (5)	0.0056 (5)
C3	0.0439 (6)	0.0430 (6)	0.0295 (5)	−0.0038 (5)	0.0015 (5)	0.0042 (5)
C6	0.0429 (7)	0.0407 (6)	0.0354 (6)	−0.0005 (5)	−0.0017 (5)	−0.0073 (5)
C4	0.0486 (7)	0.0446 (7)	0.0398 (6)	−0.0084 (6)	0.0028 (5)	0.0065 (5)
C15	0.0511 (8)	0.0542 (8)	0.0453 (7)	−0.0084 (6)	−0.0059 (6)	−0.0035 (6)
C5	0.0467 (7)	0.0403 (6)	0.0473 (7)	−0.0074 (6)	−0.0016 (6)	−0.0038 (5)

S1—C7	1.7318 (12)	C7—C6	1.3925 (17)
S1—C1	1.7539 (11)	C9—C10	1.3718 (18)
N1—C1	1.3067 (14)	C9—H9	0.9300
N1—C2	1.3864 (15)	C14—C15	1.5010 (18)
C8—C13	1.4028 (15)	C14—H14A	0.9700
C8—C9	1.4082 (15)	C14—H14B	0.9700
C8—C1	1.4575 (16)	C10—H10	0.9300
C13—O1	1.3464 (13)	C3—C4	1.3750 (18)
C13—C12	1.4105 (16)	C3—H3	0.9300
O2—C12	1.3600 (14)	C6—C5	1.3809 (19)
O2—C14	1.4330 (14)	C6—H6	0.9300
O1—H1	0.8200	C4—C5	1.3950 (19)
C12—C11	1.3825 (16)	C4—H4	0.9300
C11—C10	1.3881 (18)	C15—H15A	0.9600
C11—H11	0.9300	C15—H15B	0.9600
C2—C3	1.3941 (16)	C15—H15C	0.9600
C2—C7	1.4044 (15)	C5—H5	0.9300

C7—S1—C1	89.48 (5)	O2—C14—C15	106.25 (10)
C1—N1—C2	111.47 (9)	O2—C14—H14A	110.5
C13—C8—C9	118.96 (11)	C15—C14—H14A	110.5
C13—C8—C1	119.77 (10)	O2—C14—H14B	110.5
C9—C8—C1	121.26 (10)	C15—C14—H14B	110.5
O1—C13—C8	123.48 (10)	H14A—C14—H14B	108.7
O1—C13—C12	116.80 (10)	C9—C10—C11	120.67 (11)
C8—C13—C12	119.71 (10)	C9—C10—H10	119.7
C12—O2—C14	118.02 (9)	C11—C10—H10	119.7
C13—O1—H1	109.5	C4—C3—C2	118.76 (11)
N1—C1—C8	123.20 (10)	C4—C3—H3	120.6
N1—C1—S1	114.80 (9)	C2—C3—H3	120.6
C8—C1—S1	122.00 (8)	C5—C6—C7	117.51 (11)
O2—C12—C11	125.61 (11)	C5—C6—H6	121.2
O2—C12—C13	114.48 (10)	C7—C6—H6	121.2
C11—C12—C13	119.91 (11)	C3—C4—C5	121.05 (12)
C12—C11—C10	120.22 (11)	C3—C4—H4	119.5
C12—C11—H11	119.9	C5—C4—H4	119.5
C10—C11—H11	119.9	C14—C15—H15A	109.5
N1—C2—C3	125.53 (10)	C14—C15—H15B	109.5
N1—C2—C7	114.76 (10)	H15A—C15—H15B	109.5
C3—C2—C7	119.71 (11)	C14—C15—H15C	109.5
C6—C7—C2	121.56 (11)	H15A—C15—H15C	109.5
C6—C7—S1	128.96 (9)	H15B—C15—H15C	109.5
C2—C7—S1	109.48 (8)	C6—C5—C4	121.42 (12)
C10—C9—C8	120.53 (11)	C6—C5—H5	119.3
C10—C9—H9	119.7	C4—C5—H5	119.3
C8—C9—H9	119.7

C9—C8—C13—O1	−178.87 (11)	C1—N1—C2—C3	178.53 (11)
C1—C8—C13—O1	0.34 (17)	C1—N1—C2—C7	−0.66 (14)
C9—C8—C13—C12	0.68 (17)	N1—C2—C7—C6	179.82 (10)
C1—C8—C13—C12	179.89 (10)	C3—C2—C7—C6	0.58 (17)
C2—N1—C1—C8	179.89 (10)	N1—C2—C7—S1	0.53 (12)
C2—N1—C1—S1	0.49 (13)	C3—C2—C7—S1	−178.70 (9)
C13—C8—C1—N1	−3.48 (17)	C1—S1—C7—C6	−179.43 (12)
C9—C8—C1—N1	175.71 (11)	C1—S1—C7—C2	−0.21 (8)
C13—C8—C1—S1	175.88 (8)	C13—C8—C9—C10	−0.23 (18)
C9—C8—C1—S1	−4.93 (16)	C1—C8—C9—C10	−179.43 (11)
C7—S1—C1—N1	−0.16 (9)	C12—O2—C14—C15	−178.61 (11)
C7—S1—C1—C8	−179.57 (10)	C8—C9—C10—C11	−0.3 (2)
C14—O2—C12—C11	1.21 (18)	C12—C11—C10—C9	0.4 (2)
C14—O2—C12—C13	−179.35 (10)	N1—C2—C3—C4	−179.61 (11)
O1—C13—C12—O2	−0.50 (15)	C7—C2—C3—C4	−0.46 (18)
C8—C13—C12—O2	179.92 (10)	C2—C7—C6—C5	−0.25 (18)
O1—C13—C12—C11	178.97 (11)	S1—C7—C6—C5	178.88 (10)
C8—C13—C12—C11	−0.61 (17)	C2—C3—C4—C5	0.0 (2)
O2—C12—C11—C10	179.49 (12)	C7—C6—C5—C4	−0.2 (2)
C13—C12—C11—C10	0.08 (18)	C3—C4—C5—C6	0.3 (2)

Cg1 and Cg2 are the centroids of the C8–C13 and C2–C7 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.90	2.626 (1)	147
C14—H14A···Cg1ⁱ	0.97	2.91	3.779 (1)	149
C14—H14B···Cg2ⁱⁱ	0.97	2.65	3.506 (1)	148

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C8–C13 and C2–C7 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.90	2.626 (1)	147
C14—H14A⋯Cg1ⁱ	0.97	2.91	3.779 (1)	149
C14—H14B⋯Cg2ⁱⁱ	0.97	2.65	3.506 (1)	148

Symmetry codes: (i) ; (ii) .

7 in total

1. A short history of SHELX.

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

2. Antitumor benzothiazoles. 16. Synthesis and pharmaceutical properties of antitumor 2-(4-aminophenyl)benzothiazole amino acid prodrugs.

Authors: Ian Hutchinson; Sharon A Jennings; B Rao Vishnuvajjala; Andrew D Westwell; Malcolm F G Stevens
Journal: J Med Chem Date: 2002-01-31 Impact factor: 7.446

3. In vitro activities of position 2 substitution-bearing 6-nitro- and 6-amino-benzothiazoles and their corresponding anthranilic acid derivatives against Leishmania infantum and Trichomonas vaginalis.

Authors: Florence Delmas; Carole Di Giorgio; Maxime Robin; Nadine Azas; Monique Gasquet; Claire Detang; Muriel Costa; Pierre Timon-David; Jean-Pierre Galy
Journal: Antimicrob Agents Chemother Date: 2002-08 Impact factor: 5.191

4. 3-(Benzothia-zol-2-yl)-3-(prop-2-yn-yl)hex-5-yn-2-one.

Authors: Yamna Baryala; Abdelfettah Zerzouf; Moussa Salem; El Mokhtar Essassi; Lahcen El Ammari
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-03-17

5. 2-(4-Amino-phen-yl)-1,3-benzothia-zole.

Authors: Yong Zhang; Zhen-Hong Su; Qing-Zhi Wang; Lei Teng
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-10-04

6. In vitro evaluation of amino acid prodrugs of novel antitumour 2-(4-amino-3-methylphenyl)benzothiazoles.

Authors: T D Bradshaw; M-S Chua; H L Browne; V Trapani; E A Sausville; M F G Stevens
Journal: Br J Cancer Date: 2002-04-22 Impact factor: 7.640

7. Structure validation in chemical crystallography.

Authors: Anthony L Spek
Journal: Acta Crystallogr D Biol Crystallogr Date: 2009-01-20