Literature DB >> 21588430

Ethyl 2-[4-(1,3-benzothiazol-2-yl)-anilino]acetate.

Yong Zhang1, Yuan Qu, Bi-Lin Zhao.   

Abstract

In the title compound, C(17)H(16)N(2)O(2)S, the dihedral angle between the benzothia-zole ring system and the benzene ring is 1.20 (2)°. The substituted amino substituent is in an extended conformation with an N-C-C-O torsion angle of 179.4 (3)°. In the crystal structure, pairs of mol-ecules are connected by inter-molecular N-H⋯O and weak C-H⋯O hydrogen bonds, forming centrosymmetric dimers.

Entities:  

Year:  2010        PMID： 21588430      PMCID： PMC3007372          DOI： 10.1107/S1600536810029442

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


Related literature

For background to thio­flavin T (ThT), a benzothia­zole dye that exhibits enhanced fluorescence upon binding to amyloid fibrils, and its derivatives, see: Kung et al. (2001 ▶); Qu et al. (2007 ▶); Zhang & Zhao (2009 ▶). For the synthesis, see: Stephenson et al. (2007 ▶).

Experimental

Crystal data

C17H16N2O2S M = 312.38 Monoclinic, a = 5.6303 (1) Å b = 26.1604 (5) Å c = 10.5989 (2) Å β = 98.294 (1)° V = 1544.79 (5) Å3 Z = 4 Mo Kα radiation μ = 0.22 mm−1 T = 298 K 0.36 × 0.24 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.926, T max = 0.956 11631 measured reflections 3808 independent reflections 3015 reflections with I > 2σ(I) R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.058 wR(F 2) = 0.145 S = 1.07 3808 reflections 203 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.39 e Å−3 Δρmin = −0.30 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/S1600536810029442/lh5087sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029442/lh5087Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H16N2O2SF(000) = 656
Mr = 312.38Dx = 1.343 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3368 reflections
a = 5.6303 (1) Åθ = 2.5–26.1°
b = 26.1604 (5) ŵ = 0.22 mm−1
c = 10.5989 (2) ÅT = 298 K
β = 98.294 (1)°Block, pale-yellow
V = 1544.79 (5) Å30.36 × 0.24 × 0.21 mm
Z = 4
Bruker SMART CCD area-detector diffractometer3808 independent reflections
Radiation source: fine-focus sealed tube3015 reflections with I > 2σ(I)
graphiteRint = 0.076
φ and ω scansθmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −7→6
Tmin = 0.926, Tmax = 0.956k = −34→34
11631 measured reflectionsl = −10→14
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H atoms treated by a mixture of independent and constrained refinement
S = 1.07w = 1/[σ2(Fo2) + (0.0584P)2 + 0.2785P] where P = (Fo2 + 2Fc2)/3
3808 reflections(Δ/σ)max < 0.001
203 parametersΔρmax = 0.39 e Å−3
1 restraintΔρmin = −0.30 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
C10.4095 (4)0.16282 (7)1.27189 (19)0.0459 (4)
C20.5567 (4)0.18305 (9)1.3771 (2)0.0584 (6)
H20.70500.16851.40670.070*
C30.4757 (5)0.22514 (9)1.4357 (2)0.0624 (6)
H30.57120.23971.50540.075*
C40.2521 (5)0.24629 (8)1.3919 (2)0.0614 (6)
H40.20070.27481.43300.074*
C50.1066 (4)0.22608 (8)1.2896 (2)0.0552 (5)
H5−0.04260.24061.26180.066*
C60.1840 (3)0.18348 (7)1.22724 (19)0.0429 (4)
C70.1778 (3)0.12057 (7)1.08723 (18)0.0388 (4)
C80.0933 (3)0.08695 (7)0.98019 (17)0.0383 (4)
C90.2312 (3)0.04687 (7)0.94479 (19)0.0459 (5)
H90.38150.04080.99150.055*
C100.1514 (3)0.01576 (7)0.84224 (19)0.0461 (5)
H100.2472−0.01100.82140.055*
C11−0.0722 (3)0.02423 (7)0.76967 (18)0.0404 (4)
C12−0.2144 (3)0.06424 (7)0.80651 (19)0.0444 (4)
H12−0.36570.07010.76080.053*
C13−0.1326 (3)0.09459 (7)0.90894 (19)0.0440 (4)
H13−0.22950.12090.93150.053*
C14−0.0362 (3)−0.04854 (7)0.62537 (19)0.0448 (4)
H14A−0.0175−0.07340.69410.054*
H14B0.1222−0.03940.60680.054*
C15−0.1818 (3)−0.07146 (7)0.50852 (19)0.0439 (4)
C16−0.1958 (4)−0.13779 (8)0.3566 (2)0.0503 (5)
H16A−0.2157−0.11380.28600.060*
H16B−0.3530−0.15020.36940.060*
C17−0.0407 (4)−0.18121 (8)0.3288 (2)0.0621 (6)
H17A0.1178−0.16880.32280.093*
H17B−0.1070−0.19680.24950.093*
H17C−0.0329−0.20600.39610.093*
N10.0567 (3)0.15892 (6)1.12304 (15)0.0441 (4)
N2−0.1552 (3)−0.00386 (7)0.66362 (18)0.0538 (5)
H2A−0.294 (2)0.0014 (8)0.622 (2)0.065*
O1−0.0780 (3)−0.11295 (5)0.47181 (14)0.0506 (4)
O2−0.3671 (3)−0.05410 (6)0.45639 (16)0.0655 (5)
S10.46125 (9)0.11103 (2)1.17793 (6)0.05496 (19)
U11U22U33U12U13U23
C10.0511 (11)0.0454 (10)0.0419 (11)−0.0041 (8)0.0096 (9)−0.0032 (8)
C20.0616 (13)0.0634 (13)0.0489 (13)−0.0079 (10)0.0030 (10)−0.0080 (10)
C30.0821 (16)0.0581 (13)0.0474 (13)−0.0199 (12)0.0104 (11)−0.0098 (10)
C40.0927 (17)0.0426 (11)0.0531 (13)−0.0085 (11)0.0250 (13)−0.0090 (10)
C50.0695 (13)0.0426 (11)0.0554 (13)0.0028 (9)0.0160 (11)−0.0009 (10)
C60.0519 (11)0.0375 (9)0.0409 (10)−0.0028 (8)0.0121 (8)0.0019 (8)
C70.0396 (9)0.0392 (9)0.0374 (10)0.0001 (7)0.0049 (7)0.0034 (7)
C80.0394 (9)0.0394 (9)0.0362 (10)−0.0009 (7)0.0056 (7)0.0017 (7)
C90.0423 (10)0.0463 (10)0.0463 (11)0.0070 (8)−0.0032 (8)−0.0016 (9)
C100.0485 (10)0.0402 (10)0.0476 (12)0.0084 (8)0.0004 (9)−0.0051 (8)
C110.0428 (9)0.0380 (9)0.0399 (10)−0.0026 (7)0.0038 (8)0.0003 (8)
C120.0364 (9)0.0493 (10)0.0459 (11)0.0039 (7)0.0011 (8)−0.0025 (9)
C130.0422 (10)0.0439 (10)0.0463 (11)0.0056 (8)0.0073 (8)−0.0023 (8)
C140.0470 (10)0.0422 (10)0.0432 (11)0.0000 (8)0.0001 (8)−0.0022 (8)
C150.0479 (10)0.0413 (10)0.0421 (11)−0.0022 (8)0.0051 (8)−0.0011 (8)
C160.0563 (12)0.0487 (11)0.0455 (12)−0.0081 (9)0.0052 (9)−0.0084 (9)
C170.0786 (15)0.0489 (12)0.0609 (15)−0.0035 (11)0.0173 (12)−0.0134 (11)
N10.0489 (9)0.0400 (8)0.0430 (9)0.0032 (7)0.0056 (7)0.0004 (7)
N20.0507 (10)0.0511 (10)0.0544 (11)0.0084 (8)−0.0106 (8)−0.0151 (8)
O10.0578 (8)0.0440 (7)0.0478 (9)0.0042 (6)0.0004 (6)−0.0084 (6)
O20.0596 (9)0.0661 (10)0.0640 (11)0.0166 (7)−0.0141 (8)−0.0198 (8)
S10.0455 (3)0.0623 (3)0.0537 (4)0.0105 (2)−0.0047 (2)−0.0168 (3)
C1—C21.394 (3)C10—H100.9300
C1—C61.398 (3)C11—N21.367 (2)
C1—S11.731 (2)C11—C121.407 (3)
C2—C31.374 (3)C12—C131.370 (3)
C2—H20.9300C12—H120.9300
C3—C41.392 (4)C13—H130.9300
C3—H30.9300C14—N21.434 (2)
C4—C51.367 (3)C14—C151.507 (3)
C4—H40.9300C14—H14A0.9700
C5—C61.397 (3)C14—H14B0.9700
C5—H50.9300C15—O21.197 (2)
C6—N11.385 (2)C15—O11.318 (2)
C7—N11.300 (2)C16—O11.456 (2)
C7—C81.460 (3)C16—C171.488 (3)
C7—S11.7579 (18)C16—H16A0.9700
C8—C91.388 (3)C16—H16B0.9700
C8—C131.397 (3)C17—H17A0.9600
C9—C101.380 (3)C17—H17B0.9600
C9—H90.9300C17—H17C0.9600
C10—C111.395 (3)N2—H2A0.853 (9)
C2—C1—C6122.01 (19)C13—C12—C11120.77 (17)
C2—C1—S1128.85 (17)C13—C12—H12119.6
C6—C1—S1109.13 (14)C11—C12—H12119.6
C3—C2—C1117.9 (2)C12—C13—C8121.42 (17)
C3—C2—H2121.1C12—C13—H13119.3
C1—C2—H2121.1C8—C13—H13119.3
C2—C3—C4120.7 (2)N2—C14—C15109.62 (15)
C2—C3—H3119.6N2—C14—H14A109.7
C4—C3—H3119.6C15—C14—H14A109.7
C5—C4—C3121.4 (2)N2—C14—H14B109.7
C5—C4—H4119.3C15—C14—H14B109.7
C3—C4—H4119.3H14A—C14—H14B108.2
C4—C5—C6119.4 (2)O2—C15—O1124.76 (18)
C4—C5—H5120.3O2—C15—C14124.23 (18)
C6—C5—H5120.3O1—C15—C14111.01 (16)
N1—C6—C5125.91 (19)O1—C16—C17107.31 (17)
N1—C6—C1115.52 (16)O1—C16—H16A110.3
C5—C6—C1118.57 (19)C17—C16—H16A110.3
N1—C7—C8124.46 (16)O1—C16—H16B110.3
N1—C7—S1115.02 (14)C17—C16—H16B110.3
C8—C7—S1120.52 (13)H16A—C16—H16B108.5
C9—C8—C13117.59 (17)C16—C17—H17A109.5
C9—C8—C7122.20 (16)C16—C17—H17B109.5
C13—C8—C7120.21 (16)H17A—C17—H17B109.5
C10—C9—C8121.81 (17)C16—C17—H17C109.5
C10—C9—H9119.1H17A—C17—H17C109.5
C8—C9—H9119.1H17B—C17—H17C109.5
C9—C10—C11120.39 (17)C7—N1—C6110.97 (16)
C9—C10—H10119.8C11—N2—C14123.52 (16)
C11—C10—H10119.8C11—N2—H2A121.2 (16)
N2—C11—C10122.80 (17)C14—N2—H2A114.6 (16)
N2—C11—C12119.18 (16)C15—O1—C16116.58 (16)
C10—C11—C12118.00 (17)C1—S1—C789.35 (9)
C6—C1—C2—C3−1.2 (3)C10—C11—C12—C131.5 (3)
S1—C1—C2—C3179.40 (17)C11—C12—C13—C8−0.1 (3)
C1—C2—C3—C40.8 (3)C9—C8—C13—C12−1.0 (3)
C2—C3—C4—C5−0.1 (4)C7—C8—C13—C12178.72 (17)
C3—C4—C5—C6−0.3 (3)N2—C14—C15—O20.6 (3)
C4—C5—C6—N1179.89 (19)N2—C14—C15—O1−179.36 (16)
C4—C5—C6—C10.0 (3)C8—C7—N1—C6180.00 (16)
C2—C1—C6—N1−179.10 (18)S1—C7—N1—C6−0.2 (2)
S1—C1—C6—N10.4 (2)C5—C6—N1—C7179.97 (18)
C2—C1—C6—C50.8 (3)C1—C6—N1—C7−0.1 (2)
S1—C1—C6—C5−179.68 (15)C10—C11—N2—C148.1 (3)
N1—C7—C8—C9179.13 (18)C12—C11—N2—C14−173.43 (19)
S1—C7—C8—C9−0.6 (3)C15—C14—N2—C11177.26 (18)
N1—C7—C8—C13−0.6 (3)O2—C15—O1—C162.3 (3)
S1—C7—C8—C13179.68 (14)C14—C15—O1—C16−177.66 (16)
C13—C8—C9—C100.7 (3)C17—C16—O1—C15176.34 (17)
C7—C8—C9—C10−178.98 (18)C2—C1—S1—C7179.0 (2)
C8—C9—C10—C110.6 (3)C6—C1—S1—C7−0.41 (15)
C9—C10—C11—N2176.82 (19)N1—C7—S1—C10.39 (15)
C9—C10—C11—C12−1.7 (3)C8—C7—S1—C1−179.83 (16)
N2—C11—C12—C13−177.13 (19)
D—H···AD—HH···AD···AD—H···A
C12—H12···O2i0.932.603.390 (2)144
N2—H2A···O2i0.85 (1)2.40 (1)3.188 (2)154 (2)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C12—H12⋯O2i0.932.603.390 (2)144
N2—H2A⋯O2i0.85 (1)2.40 (1)3.188 (2)154 (2)

Symmetry code: (i) .

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