Literature DB >> 21578356

2-{[4-(1,3-Benzothia-zol-2-yl)phen-yl](meth-yl)amino}acetic acid.

Yong Zhang1, Bi-Lin Zhao.   

Abstract

In the title compound, C(16)H(14)N(2)O(2)S, the dihedral angle between the benzothia-zole ring system and benzene ring is 3.11 (2)°. In the crystal structure, inter-molecular O-H⋯N hydrogen bonds link mol-ecules into chains along [100] and these chains are, in turn, linked into a three-dimensional network via weak inter-molecular C-H⋯O hydrogen bonds.

Entities:  

Year:  2009        PMID： 21578356      PMCID： PMC2971184          DOI： 10.1107/S1600536809041452

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


Related literature

In an effort to develop in vivo β-sheet imaging probes, many derivatives of thio­flavin T, a water-soluble fluorescent dye, have been synthesized and evaluated, see: Kung et al. (2001 ▶); Qu et al. (2007 ▶). For the synthetic procedure, see: Stephenson et al., 2007 ▶.

Experimental

Crystal data

C16H14N2O2S M = 298.35 Orthorhombic, a = 11.9516 (10) Å b = 9.4390 (8) Å c = 25.418 (2) Å V = 2867.5 (4) Å3 Z = 8 Mo Kα radiation μ = 0.23 mm−1 T = 298 K 0.16 × 0.15 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.964, T max = 0.973 12100 measured reflections 3234 independent reflections 2156 reflections with I > 2σ(I) R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.059 wR(F 2) = 0.134 S = 1.06 3234 reflections 194 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.26 e Å−3 Δρmin = −0.18 e Å−3 Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809041452/lh2913sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041452/lh2913Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H14N2O2SF(000) = 1248
Mr = 298.35Dx = 1.382 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 1634 reflections
a = 11.9516 (10) Åθ = 2.3–22.4°
b = 9.4390 (8) ŵ = 0.23 mm−1
c = 25.418 (2) ÅT = 298 K
V = 2867.5 (4) Å3Block, colorless
Z = 80.16 × 0.15 × 0.12 mm
Bruker SMART CCD diffractometer3234 independent reflections
Radiation source: fine-focus sealed tube2156 reflections with I > 2σ(I)
graphiteRint = 0.057
φ and ω scansθmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −15→6
Tmin = 0.964, Tmax = 0.973k = −11→12
12100 measured reflectionsl = −31→31
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.0495P)2] where P = (Fo2 + 2Fc2)/3
3234 reflections(Δ/σ)max < 0.001
194 parametersΔρmax = 0.26 e Å−3
0 restraintsΔρmin = −0.18 e Å−3
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.
xyzUiso*/Ueq
C10.36303 (18)0.1030 (2)0.62901 (9)0.0352 (6)
C20.3131 (2)−0.0017 (3)0.71444 (10)0.0448 (6)
C30.2757 (3)−0.0521 (3)0.76272 (11)0.0604 (8)
H30.2112−0.01600.77830.072*
C40.3367 (3)−0.1562 (3)0.78658 (11)0.0654 (9)
H40.3122−0.19320.81850.079*
C50.4342 (3)−0.2081 (3)0.76424 (11)0.0599 (8)
H50.4747−0.27780.78170.072*
C60.4720 (2)−0.1582 (3)0.71657 (10)0.0483 (7)
H60.5374−0.19370.70170.058*
C70.4106 (2)−0.0537 (3)0.69110 (10)0.0386 (6)
C80.36685 (18)0.1881 (2)0.58153 (9)0.0347 (6)
C90.28533 (19)0.2883 (3)0.56974 (10)0.0408 (6)
H90.22510.29930.59260.049*
C100.2907 (2)0.3716 (3)0.52558 (10)0.0422 (6)
H100.23340.43570.51880.051*
C110.38126 (18)0.3618 (2)0.49032 (9)0.0344 (6)
C120.46109 (19)0.2571 (3)0.50147 (9)0.0409 (6)
H120.52060.24380.47840.049*
C130.45351 (19)0.1741 (3)0.54534 (10)0.0419 (6)
H130.50820.10590.55120.050*
C140.3081 (2)0.5541 (2)0.43544 (10)0.0432 (6)
H14A0.34190.62910.41470.052*
H14B0.28040.59590.46780.052*
C150.21108 (19)0.4931 (3)0.40533 (9)0.0368 (6)
C160.4788 (2)0.4267 (3)0.40869 (11)0.0550 (8)
H16A0.55100.42520.42520.082*
H16B0.47650.50130.38310.082*
H16C0.46550.33740.39170.082*
N10.43700 (15)0.0080 (2)0.64281 (8)0.0372 (5)
N20.39284 (16)0.4510 (2)0.44825 (8)0.0421 (5)
O10.13080 (15)0.58713 (18)0.39831 (8)0.0520 (5)
H10.065 (2)0.540 (3)0.3813 (11)0.078*
O20.20655 (15)0.37398 (19)0.38956 (8)0.0583 (5)
S10.25427 (6)0.12637 (8)0.67437 (3)0.0549 (3)
U11U22U33U12U13U23
C10.0333 (12)0.0360 (14)0.0363 (14)−0.0010 (10)−0.0001 (11)−0.0032 (11)
C20.0506 (15)0.0454 (15)0.0384 (15)0.0003 (13)0.0038 (12)0.0027 (13)
C30.075 (2)0.063 (2)0.0438 (18)−0.0004 (16)0.0151 (15)0.0044 (16)
C40.096 (3)0.064 (2)0.0361 (17)−0.0114 (18)0.0031 (17)0.0104 (15)
C50.075 (2)0.0537 (19)0.0507 (19)−0.0072 (16)−0.0165 (17)0.0119 (15)
C60.0468 (15)0.0481 (17)0.0500 (18)−0.0014 (12)−0.0079 (13)0.0083 (14)
C70.0409 (13)0.0366 (14)0.0382 (15)−0.0057 (11)−0.0041 (12)0.0019 (12)
C80.0352 (12)0.0349 (13)0.0339 (14)−0.0012 (11)−0.0016 (11)0.0002 (11)
C90.0354 (13)0.0442 (15)0.0429 (16)0.0037 (11)0.0052 (11)−0.0003 (13)
C100.0396 (13)0.0380 (14)0.0490 (17)0.0071 (11)−0.0049 (12)0.0035 (13)
C110.0333 (12)0.0351 (13)0.0348 (14)−0.0058 (10)−0.0085 (10)−0.0013 (11)
C120.0358 (13)0.0518 (16)0.0351 (15)0.0058 (11)0.0029 (11)0.0043 (12)
C130.0371 (13)0.0488 (16)0.0399 (15)0.0107 (11)−0.0021 (12)0.0042 (13)
C140.0538 (15)0.0338 (14)0.0419 (15)−0.0024 (12)−0.0093 (13)0.0073 (12)
C150.0433 (13)0.0327 (14)0.0345 (14)−0.0036 (11)−0.0002 (11)0.0057 (11)
C160.0535 (16)0.0594 (19)0.0520 (18)−0.0068 (14)0.0062 (14)0.0155 (15)
N10.0332 (10)0.0386 (12)0.0398 (12)−0.0026 (9)−0.0011 (9)0.0040 (10)
N20.0408 (11)0.0411 (12)0.0444 (13)0.0004 (10)−0.0046 (10)0.0112 (10)
O10.0432 (10)0.0364 (10)0.0762 (14)0.0012 (8)−0.0150 (10)−0.0006 (9)
O20.0598 (12)0.0422 (12)0.0727 (14)0.0036 (9)−0.0132 (11)−0.0167 (10)
S10.0550 (4)0.0613 (5)0.0484 (5)0.0181 (3)0.0152 (3)0.0110 (4)
C1—N11.307 (3)C10—C111.408 (3)
C1—C81.450 (3)C10—H100.9300
C1—S11.752 (2)C11—N21.368 (3)
C2—C31.390 (3)C11—C121.403 (3)
C2—C71.397 (3)C12—C131.366 (3)
C2—S11.730 (3)C12—H120.9300
C3—C41.366 (4)C13—H130.9300
C3—H30.9300C14—N21.441 (3)
C4—C51.386 (4)C14—C151.504 (3)
C4—H40.9300C14—H14A0.9700
C5—C61.377 (4)C14—H14B0.9700
C5—H50.9300C15—O21.195 (3)
C6—C71.390 (3)C15—O11.319 (3)
C6—H60.9300C16—N21.456 (3)
C7—N11.395 (3)C16—H16A0.9600
C8—C91.391 (3)C16—H16B0.9600
C8—C131.392 (3)C16—H16C0.9600
C9—C101.372 (3)O1—H11.00 (3)
C9—H90.9300
N1—C1—C8125.6 (2)N2—C11—C12121.5 (2)
N1—C1—S1114.31 (18)N2—C11—C10122.4 (2)
C8—C1—S1120.10 (17)C12—C11—C10116.1 (2)
C3—C2—C7121.5 (3)C13—C12—C11121.6 (2)
C3—C2—S1128.9 (2)C13—C12—H12119.2
C7—C2—S1109.53 (18)C11—C12—H12119.2
C4—C3—C2117.8 (3)C12—C13—C8122.3 (2)
C4—C3—H3121.1C12—C13—H13118.8
C2—C3—H3121.1C8—C13—H13118.8
C3—C4—C5121.4 (3)N2—C14—C15113.5 (2)
C3—C4—H4119.3N2—C14—H14A108.9
C5—C4—H4119.3C15—C14—H14A108.9
C6—C5—C4121.1 (3)N2—C14—H14B108.9
C6—C5—H5119.5C15—C14—H14B108.9
C4—C5—H5119.5H14A—C14—H14B107.7
C5—C6—C7118.6 (3)O2—C15—O1123.7 (2)
C5—C6—H6120.7O2—C15—C14124.4 (2)
C7—C6—H6120.7O1—C15—C14111.9 (2)
C6—C7—N1125.9 (2)N2—C16—H16A109.5
C6—C7—C2119.5 (2)N2—C16—H16B109.5
N1—C7—C2114.6 (2)H16A—C16—H16B109.5
C9—C8—C13116.3 (2)N2—C16—H16C109.5
C9—C8—C1122.3 (2)H16A—C16—H16C109.5
C13—C8—C1121.4 (2)H16B—C16—H16C109.5
C10—C9—C8122.2 (2)C1—N1—C7111.7 (2)
C10—C9—H9118.9C11—N2—C14121.4 (2)
C8—C9—H9118.9C11—N2—C16121.0 (2)
C9—C10—C11121.3 (2)C14—N2—C16116.5 (2)
C9—C10—H10119.3C15—O1—H1109.4 (16)
C11—C10—H10119.3C2—S1—C189.89 (12)
C7—C2—C3—C4−0.9 (4)C10—C11—C12—C13−2.9 (3)
S1—C2—C3—C4179.1 (2)C11—C12—C13—C8−0.1 (4)
C2—C3—C4—C51.6 (5)C9—C8—C13—C122.2 (4)
C3—C4—C5—C6−1.3 (5)C1—C8—C13—C12−177.3 (2)
C4—C5—C6—C70.3 (4)N2—C14—C15—O2−5.5 (4)
C5—C6—C7—N1−179.9 (2)N2—C14—C15—O1174.4 (2)
C5—C6—C7—C20.3 (4)C8—C1—N1—C7178.9 (2)
C3—C2—C7—C60.0 (4)S1—C1—N1—C70.4 (3)
S1—C2—C7—C6180.00 (19)C6—C7—N1—C1179.8 (2)
C3—C2—C7—N1−179.8 (2)C2—C7—N1—C1−0.4 (3)
S1—C2—C7—N10.2 (3)C12—C11—N2—C14177.0 (2)
N1—C1—C8—C9−179.4 (2)C10—C11—N2—C14−4.5 (3)
S1—C1—C8—C9−1.0 (3)C12—C11—N2—C169.8 (3)
N1—C1—C8—C130.1 (4)C10—C11—N2—C16−171.8 (2)
S1—C1—C8—C13178.57 (18)C15—C14—N2—C11−81.0 (3)
C13—C8—C9—C10−1.4 (4)C15—C14—N2—C1686.8 (3)
C1—C8—C9—C10178.1 (2)C3—C2—S1—C1180.0 (3)
C8—C9—C10—C11−1.5 (4)C7—C2—S1—C10.00 (19)
C9—C10—C11—N2−174.9 (2)N1—C1—S1—C2−0.23 (19)
C9—C10—C11—C123.6 (3)C8—C1—S1—C2−178.8 (2)
N2—C11—C12—C13175.7 (2)
D—H···AD—HH···AD···AD—H···A
O1—H1···N1i1.00 (3)1.71 (3)2.695 (3)167 (2)
C4—H4···O2ii0.932.503.368 (3)156
C14—H14A···O2iii0.972.473.242 (3)137
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1—H1⋯N1i1.00 (3)1.71 (3)2.695 (3)167 (2)
C4—H4⋯O2ii0.932.503.368 (3)156
C14—H14A⋯O2iii0.972.473.242 (3)137

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

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