Literature DB >> 21581724

4-(1,3-Benzothia-zol-2-yl)-N-(2-pyridylmeth-yl)aniline monohydrate.

Zhen-Hong Su, Qing-Zhi Wang, Lei Teng, Yong Zhang.   

Abstract

In the title compound, C(19)H(15)N(3)S·H(2)O, the benzothia-zole ring system forms a dihedral angle of 7.22 (1)° with the benzene ring and the benzene ring forms a dihedral angle of 80.89 (1)° with the pyridine ring. An intra-molecular N-H⋯O inter-action is present. The crystal structure is stablized by inter-molecular O-H⋯N hydrogen bonds, π-π [centroid-centroid distances = 3.782 (1), 3.946 (1) and 3.913 (1) Å] and C-H⋯π inter-actions, forming a three dimensional-network.

Entities:  

Year:  2008        PMID： 21581724      PMCID： PMC2967994          DOI： 10.1107/S1600536808041238

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


Related literature

For background information, see: Krebs et al. (2005 ▶); Kung et al. (2001 ▶); Naiki et al. (1989 ▶); Qu et al. (2007 ▶). For the synthetic procedure, see: Stephenson et al. (2007 ▶).

Experimental

Crystal data

C19H15N3S·H2O M = 335.42 Triclinic, a = 6.5042 (3) Å b = 11.5721 (5) Å c = 11.9415 (5) Å α = 99.597 (1)° β = 103.599 (1)° γ = 99.813 (1)° V = 840.52 (6) Å3 Z = 2 Mo Kα radiation μ = 0.20 mm−1 T = 298 (2) K 0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.961, T max = 0.980 5408 measured reflections 3243 independent reflections 2342 reflections with I > 2σ(I) R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.053 wR(F 2) = 0.133 S = 0.98 3243 reflections 227 parameters 4 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.25 e Å−3 Δρmin = −0.28 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808041238/lh2740sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041238/lh2740Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C19H15N3S·H2OZ = 2
Mr = 335.42F(000) = 352
Triclinic, P1Dx = 1.325 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.5042 (3) ÅCell parameters from 1809 reflections
b = 11.5721 (5) Åθ = 1.8–26.0°
c = 11.9415 (5) ŵ = 0.20 mm−1
α = 99.597 (1)°T = 298 K
β = 103.599 (1)°Plate, yellow
γ = 99.813 (1)°0.20 × 0.10 × 0.10 mm
V = 840.52 (6) Å3
Bruker SMART CCD diffractometer3243 independent reflections
Radiation source: fine-focus sealed tube2342 reflections with I > 2σ(I)
graphiteRint = 0.074
φ and ω scansθmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)h = −8→8
Tmin = 0.961, Tmax = 0.980k = −11→14
5408 measured reflectionsl = −14→10
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H atoms treated by a mixture of independent and constrained refinement
S = 0.98w = 1/[σ2(Fo2) + (0.0653P)2] where P = (Fo2 + 2Fc2)/3
3243 reflections(Δ/σ)max < 0.001
227 parametersΔρmax = 0.25 e Å−3
4 restraintsΔρmin = −0.28 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
C10.4402 (3)0.43406 (18)−0.20560 (17)0.0522 (5)
C20.5812 (4)0.4597 (2)−0.2737 (2)0.0691 (7)
H20.69170.4186−0.27620.083*
C30.5534 (5)0.5473 (2)−0.3374 (2)0.0801 (8)
H30.64790.5659−0.38260.096*
C40.3900 (5)0.6079 (2)−0.3361 (2)0.0845 (8)
H40.37480.6659−0.38100.101*
C50.2492 (5)0.5842 (2)−0.2699 (2)0.0785 (7)
H50.13820.6252−0.26920.094*
C60.2765 (4)0.49671 (19)−0.20326 (18)0.0580 (6)
C70.2929 (3)0.34399 (17)−0.08419 (16)0.0464 (5)
C80.2525 (3)0.26241 (17)−0.00708 (16)0.0463 (5)
C90.3952 (3)0.18903 (19)0.02435 (17)0.0517 (5)
H90.51940.1946−0.00200.062*
C100.3564 (3)0.10838 (19)0.09370 (17)0.0532 (5)
H100.45410.06000.11280.064*
C110.1720 (3)0.09818 (18)0.13580 (17)0.0492 (5)
C120.0305 (3)0.17363 (18)0.10587 (18)0.0529 (5)
H12−0.09180.17010.13390.064*
C130.0701 (3)0.25266 (19)0.03563 (18)0.0528 (5)
H13−0.02750.30100.01600.063*
C15−0.0523 (3)−0.00822 (19)0.24393 (18)0.0552 (5)
H15A−0.0695−0.08900.25820.066*
H15B−0.1768−0.00710.18110.066*
C16−0.0534 (3)0.07696 (18)0.35445 (16)0.0479 (5)
C170.1128 (4)0.1740 (2)0.41260 (19)0.0659 (6)
H170.23360.19120.38440.079*
C180.0975 (5)0.2455 (2)0.5135 (2)0.0775 (7)
H180.20850.31150.55420.093*
C19−0.0808 (5)0.2189 (2)0.5533 (2)0.0765 (7)
H19−0.09410.26570.62140.092*
C20−0.2392 (4)0.1217 (2)0.4904 (2)0.0727 (7)
H20−0.36090.10320.51760.087*
N10.4450 (3)0.34715 (15)−0.13801 (15)0.0531 (4)
N20.1390 (3)0.01759 (17)0.20410 (16)0.0592 (5)
H2A0.228 (3)−0.0288 (16)0.2148 (19)0.069 (7)*
N3−0.2300 (3)0.05079 (16)0.39105 (15)0.0590 (5)
O10.4135 (2)−0.14685 (15)0.26027 (16)0.0699 (5)
H1A0.526 (3)−0.0972 (19)0.299 (2)0.105*
H1B0.450 (4)−0.2003 (18)0.218 (2)0.105*
S10.12798 (10)0.44713 (5)−0.11189 (5)0.0648 (2)
U11U22U33U12U13U23
C10.0604 (12)0.0473 (12)0.0409 (11)0.0022 (10)0.0057 (10)0.0090 (9)
C20.0644 (14)0.0747 (17)0.0662 (15)0.0035 (12)0.0152 (12)0.0250 (13)
C30.0883 (18)0.0772 (18)0.0708 (16)−0.0063 (16)0.0207 (14)0.0314 (14)
C40.118 (2)0.0620 (16)0.0721 (17)0.0093 (16)0.0193 (17)0.0320 (14)
C50.111 (2)0.0603 (16)0.0683 (16)0.0275 (14)0.0192 (15)0.0222 (13)
C60.0778 (14)0.0480 (12)0.0430 (11)0.0124 (11)0.0102 (10)0.0059 (10)
C70.0538 (11)0.0440 (11)0.0377 (10)0.0095 (9)0.0104 (9)0.0024 (8)
C80.0536 (11)0.0447 (11)0.0393 (10)0.0115 (9)0.0126 (9)0.0049 (9)
C90.0516 (11)0.0609 (13)0.0463 (11)0.0149 (10)0.0177 (9)0.0129 (10)
C100.0599 (12)0.0596 (13)0.0478 (12)0.0242 (10)0.0183 (10)0.0154 (10)
C110.0603 (12)0.0486 (12)0.0399 (10)0.0139 (10)0.0165 (9)0.0069 (9)
C120.0582 (12)0.0539 (13)0.0538 (12)0.0182 (10)0.0253 (10)0.0106 (10)
C130.0606 (12)0.0497 (12)0.0528 (12)0.0207 (10)0.0192 (10)0.0098 (10)
C150.0672 (13)0.0500 (12)0.0495 (12)0.0096 (10)0.0204 (10)0.0104 (10)
C160.0602 (12)0.0452 (12)0.0395 (10)0.0091 (10)0.0133 (9)0.0149 (9)
C170.0731 (15)0.0648 (15)0.0502 (13)−0.0061 (12)0.0172 (11)0.0067 (11)
C180.0994 (19)0.0625 (16)0.0526 (14)−0.0088 (14)0.0143 (14)−0.0003 (12)
C190.120 (2)0.0629 (16)0.0481 (14)0.0175 (16)0.0324 (15)0.0041 (12)
C200.0930 (18)0.0738 (17)0.0644 (15)0.0196 (14)0.0441 (14)0.0167 (13)
N10.0573 (10)0.0527 (10)0.0500 (10)0.0111 (8)0.0145 (8)0.0145 (8)
N20.0734 (12)0.0598 (12)0.0590 (11)0.0262 (10)0.0310 (10)0.0225 (10)
N30.0709 (12)0.0540 (11)0.0558 (11)0.0069 (9)0.0288 (9)0.0125 (9)
O10.0666 (10)0.0648 (11)0.0849 (12)0.0193 (8)0.0325 (9)0.0125 (9)
S10.0899 (5)0.0624 (4)0.0565 (4)0.0371 (3)0.0298 (3)0.0170 (3)
C1—C21.389 (3)C11—C121.400 (3)
C1—C61.390 (3)C12—C131.372 (3)
C1—N11.390 (3)C12—H120.9300
C2—C31.376 (3)C13—H130.9300
C2—H20.9300C15—N21.436 (3)
C3—C41.371 (4)C15—C161.512 (3)
C3—H30.9300C15—H15A0.9700
C4—C51.366 (4)C15—H15B0.9700
C4—H40.9300C16—N31.328 (2)
C5—C61.398 (3)C16—C171.373 (3)
C5—H50.9300C17—C181.378 (3)
C6—S11.723 (2)C17—H170.9300
C7—N11.299 (3)C18—C191.361 (4)
C7—C81.458 (3)C18—H180.9300
C7—S11.757 (2)C19—C201.360 (3)
C8—C91.391 (3)C19—H190.9300
C8—C131.392 (3)C20—N31.345 (3)
C9—C101.377 (3)C20—H200.9300
C9—H90.9300N2—O12.877 (2)
C10—C111.400 (3)N2—H2A0.856 (10)
C10—H100.9300O1—H1A0.830 (9)
C11—N21.360 (3)O1—H1B0.836 (9)
C2—C1—C6119.7 (2)C12—C13—C8121.7 (2)
C2—C1—N1125.2 (2)C12—C13—H13119.1
C6—C1—N1115.02 (19)C8—C13—H13119.1
C3—C2—C1118.4 (2)N2—C15—C16115.24 (17)
C3—C2—H2120.8N2—C15—H15A108.5
C1—C2—H2120.8C16—C15—H15A108.5
C4—C3—C2121.8 (3)N2—C15—H15B108.5
C4—C3—H3119.1C16—C15—H15B108.5
C2—C3—H3119.1H15A—C15—H15B107.5
C5—C4—C3120.9 (3)N3—C16—C17122.3 (2)
C5—C4—H4119.5N3—C16—C15114.46 (18)
C3—C4—H4119.5C17—C16—C15123.3 (2)
C4—C5—C6118.2 (3)C16—C17—C18118.9 (2)
C4—C5—H5120.9C16—C17—H17120.6
C6—C5—H5120.9C18—C17—H17120.6
C1—C6—C5121.0 (2)C19—C18—C17119.6 (2)
C1—C6—S1109.75 (17)C19—C18—H18120.2
C5—C6—S1129.3 (2)C17—C18—H18120.2
N1—C7—C8124.97 (18)C20—C19—C18118.0 (2)
N1—C7—S1114.73 (15)C20—C19—H19121.0
C8—C7—S1120.30 (15)C18—C19—H19121.0
C9—C8—C13117.53 (19)N3—C20—C19123.8 (2)
C9—C8—C7120.40 (18)N3—C20—H20118.1
C13—C8—C7122.05 (19)C19—C20—H20118.1
C10—C9—C8121.39 (19)C7—N1—C1111.11 (18)
C10—C9—H9119.3C11—N2—C15124.34 (19)
C8—C9—H9119.3C11—N2—O1124.36 (14)
C9—C10—C11120.9 (2)C15—N2—O1110.78 (13)
C9—C10—H10119.5C11—N2—H2A117.8 (16)
C11—C10—H10119.5C15—N2—H2A117.1 (16)
N2—C11—C12123.07 (19)C16—N3—C20117.4 (2)
N2—C11—C10119.30 (19)N2—O1—H1A99 (2)
C12—C11—C10117.63 (19)N2—O1—H1B132 (2)
C13—C12—C11120.76 (19)H1A—O1—H1B107.1 (15)
C13—C12—H12119.6C6—S1—C789.37 (10)
C11—C12—H12119.6
C6—C1—C2—C30.0 (3)N2—C15—C16—N3−179.05 (18)
N1—C1—C2—C3179.0 (2)N2—C15—C16—C171.3 (3)
C1—C2—C3—C4−0.8 (4)N3—C16—C17—C181.1 (4)
C2—C3—C4—C50.8 (4)C15—C16—C17—C18−179.2 (2)
C3—C4—C5—C60.1 (4)C16—C17—C18—C19−0.1 (4)
C2—C1—C6—C50.9 (3)C17—C18—C19—C20−0.3 (4)
N1—C1—C6—C5−178.17 (19)C18—C19—C20—N3−0.3 (4)
C2—C1—C6—S1−179.81 (16)C8—C7—N1—C1179.53 (17)
N1—C1—C6—S11.1 (2)S1—C7—N1—C10.3 (2)
C4—C5—C6—C1−1.0 (3)C2—C1—N1—C7−179.93 (18)
C4—C5—C6—S1179.93 (19)C6—C1—N1—C7−0.9 (2)
N1—C7—C8—C97.2 (3)C12—C11—N2—C156.3 (3)
S1—C7—C8—C9−173.62 (15)C10—C11—N2—C15−174.45 (18)
N1—C7—C8—C13−171.42 (18)C12—C11—N2—O1177.22 (15)
S1—C7—C8—C137.8 (3)C10—C11—N2—O1−3.5 (3)
C13—C8—C9—C100.9 (3)C16—C15—N2—C11−84.0 (3)
C7—C8—C9—C10−177.73 (18)C16—C15—N2—O1104.04 (17)
C8—C9—C10—C11−0.5 (3)C17—C16—N3—C20−1.7 (3)
C9—C10—C11—N2−179.97 (19)C15—C16—N3—C20178.7 (2)
C9—C10—C11—C12−0.7 (3)C19—C20—N3—C161.3 (4)
N2—C11—C12—C13−179.35 (19)C1—C6—S1—C7−0.75 (15)
C10—C11—C12—C131.4 (3)C5—C6—S1—C7178.4 (2)
C11—C12—C13—C8−1.0 (3)N1—C7—S1—C60.28 (16)
C9—C8—C13—C12−0.2 (3)C8—C7—S1—C6−179.01 (16)
C7—C8—C13—C12178.42 (18)
D—H···AD—HH···AD···AD—H···A
N2—H2A···O10.86 (1)2.03 (1)2.877 (2)171 (2)
O1—H1B···N1i0.84 (1)2.10 (1)2.929 (2)170 (3)
O1—H1A···N3ii0.83 (1)2.07 (1)2.889 (2)169 (3)
C18—H18···Cgiii0.932.823.689 (3)156
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N2—H2A⋯O10.856 (10)2.030 (11)2.877 (2)171 (2)
O1—H1B⋯N1i0.836 (9)2.102 (11)2.929 (2)170 (3)
O1—H1A⋯N3ii0.830 (9)2.069 (10)2.889 (2)169 (3)
C18—H18⋯Cgiii0.932.823.689 (3)156

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

  6 in total

1.  Novel stilbenes as probes for amyloid plaques.

Authors:  H F Kung; C W Lee; Z P Zhuang; M P Kung; C Hou; K Plössl
Journal:  J Am Chem Soc       Date:  2001-12-19       Impact factor: 15.419

2.  The binding of thioflavin-T to amyloid fibrils: localisation and implications.

Authors:  M R H Krebs; E H C Bromley; A M Donald
Journal:  J Struct Biol       Date:  2005-01       Impact factor: 2.867

3.  Fluoro-pegylated (FPEG) imaging agents targeting Abeta aggregates.

Authors:  Karin A Stephenson; Rajesh Chandra; Zhi-Ping Zhuang; Catherine Hou; Shunichi Oya; Mei-Ping Kung; Hank F Kung
Journal:  Bioconjug Chem       Date:  2007 Jan-Feb       Impact factor: 4.774

4.  A short history of SHELX.

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

5.  Fluorometric determination of amyloid fibrils in vitro using the fluorescent dye, thioflavin T1.

Authors:  H Naiki; K Higuchi; M Hosokawa; T Takeda
Journal:  Anal Biochem       Date:  1989-03       Impact factor: 3.365

6.  Quick assembly of 1,4-diphenyltriazoles as probes targeting beta-amyloid aggregates in Alzheimer's disease.

Authors:  Wenchao Qu; Mei-Ping Kung; Catherine Hou; Shunichi Oya; Hank F Kung
Journal:  J Med Chem       Date:  2007-06-15       Impact factor: 7.446
  6 in total
  1 in total

1.  2-({[4-(1,3-Benzothia-zol-2-yl)phen-yl]amino}methyl)-phenol.

Authors:  Kim Potgieter; Thomas Gerber; Eric Hosten; Richard Betz
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-12-03
  1 in total

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