Literature DB >> 22259460

(S)-4-Phenyl-2-(1,2,3,4-tetra-hydro-isoquinolin-3-yl)-1,3-thia-zole.

Sunayna Pawar, Pralav Bhatt, Thavendran Govender, Hendrik G Kruger, Glenn E M Maguire.   

Abstract

In the title compound, C(18)H(16)N(2)S, the N-containing ring adopts a half-chair configuration. The crystal packing features C-H⋯N contacts. There is no π-π stacking within the crystal structure.

Entities:  

Year:  2011        PMID： 22259460      PMCID： PMC3254515          DOI： 10.1107/S1600536811052585

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


Related literature

The title compound is a potential ligand for the asymmetric Henry reaction. For the application of these ligands as catalysts, see: Chakka et al. (2010 ▶); Kawthekar et al. (2010 ▶); Peters et al. (2010 ▶); Naicker et al. (2010 ▶). For related structures, see: Naicker et al. (2011a ▶,b ▶).

Experimental

Crystal data

C18H16N2S M = 292.39 Trigonal, a = 16.223 (1) Å c = 4.8130 (3) Å V = 1097.0 (1) Å3 Z = 3 Mo Kα radiation μ = 0.22 mm−1 T = 173 K 0.20 × 0.10 × 0.09 mm

Data collection

Bruker Kappa DUO APEXII diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.958, T max = 0.981 14735 measured reflections 3676 independent reflections 3205 reflections with I > 2σ(I) R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.035 wR(F 2) = 0.084 S = 1.03 3676 reflections 194 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.23 e Å−3 Δρmin = −0.22 e Å−3 Absolute structure: Flack (1983 ▶), 1832 Friedel pairs Flack parameter: −0.02 (6) Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811052585/gw2110sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052585/gw2110Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811052585/gw2110Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C18H16N2SDx = 1.328 Mg m−3
Mr = 292.39Mo Kα radiation, λ = 0.71073 Å
Trigonal, P32Cell parameters from 14735 reflections
Hall symbol: P 32θ = 2.5–28.4°
a = 16.223 (1) ŵ = 0.22 mm−1
c = 4.8130 (3) ÅT = 173 K
V = 1097.0 (1) Å3Needle, yellow
Z = 30.20 × 0.10 × 0.09 mm
F(000) = 462
Bruker Kappa DUO APEXII diffractometer3676 independent reflections
Radiation source: fine-focus sealed tube3205 reflections with I > 2σ(I)
graphiteRint = 0.030
0.5° φ scans and ω scansθmax = 28.4°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)h = −21→21
Tmin = 0.958, Tmax = 0.981k = −21→21
14735 measured reflectionsl = −6→6
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.084w = 1/[σ2(Fo2) + (0.0433P)2 + 0.1159P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3676 reflectionsΔρmax = 0.23 e Å−3
194 parametersΔρmin = −0.22 e Å−3
1 restraintAbsolute structure: Flack (1983), 1832 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.02 (6)
Experimental. Half sphere of data collected using the Bruker SAINT software package. Crystal to detector distance = 30 mm; combination of φ and ω scans of 0.5°, 60 s per °, 2 iterations.
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
S10.00297 (4)0.88075 (3)0.01223 (14)0.04813 (15)
N1−0.22129 (10)0.70793 (10)0.1094 (3)0.0316 (3)
H1N−0.2357 (14)0.6647 (15)−0.032 (4)0.036 (5)*
N2−0.01656 (9)0.71580 (9)−0.0576 (3)0.0287 (3)
C1−0.30267 (13)0.67560 (13)0.2960 (4)0.0359 (4)
H1A−0.36030.65690.18250.043*
H1B−0.29260.72980.41420.043*
C2−0.32126 (11)0.59286 (11)0.4831 (4)0.0287 (3)
C3−0.40599 (13)0.54595 (12)0.6353 (4)0.0359 (4)
H3−0.45200.56550.61740.043*
C4−0.42359 (13)0.47165 (13)0.8110 (4)0.0393 (4)
H4−0.48160.44020.91220.047*
C5−0.35671 (14)0.44283 (12)0.8399 (4)0.0385 (4)
H5−0.36880.39150.95990.046*
C6−0.27209 (13)0.48947 (12)0.6927 (4)0.0323 (4)
H6−0.22600.47020.71450.039*
C7−0.25347 (12)0.56434 (11)0.5129 (3)0.0272 (3)
C8−0.16028 (11)0.61485 (12)0.3565 (4)0.0290 (3)
H8A−0.16300.57590.19450.035*
H8B−0.10800.62220.47910.035*
C9−0.13971 (12)0.71258 (12)0.2570 (4)0.0307 (4)
H9−0.12680.75380.42440.037*
C10−0.05355 (12)0.75944 (11)0.0730 (4)0.0300 (3)
C110.08088 (13)0.87065 (13)−0.2040 (4)0.0388 (4)
H110.13140.9222−0.30070.047*
C120.06065 (11)0.77863 (11)−0.2186 (4)0.0297 (3)
C130.11195 (12)0.74191 (12)−0.3839 (4)0.0304 (4)
C140.08499 (13)0.64602 (13)−0.3768 (4)0.0362 (4)
H140.03360.6036−0.26160.043*
C150.13257 (14)0.61174 (14)−0.5369 (5)0.0433 (4)
H150.11350.5460−0.53040.052*
C160.20739 (14)0.67241 (16)−0.7052 (5)0.0468 (5)
H160.23980.6489−0.81500.056*
C170.23454 (16)0.76791 (16)−0.7122 (5)0.0506 (5)
H170.28600.8102−0.82750.061*
C180.18785 (15)0.80224 (15)−0.5542 (4)0.0435 (5)
H180.20760.8681−0.56110.052*
U11U22U33U12U13U23
S10.0455 (3)0.0274 (2)0.0703 (3)0.0174 (2)0.0198 (3)0.0061 (2)
N10.0336 (7)0.0316 (7)0.0329 (8)0.0188 (6)0.0027 (6)−0.0008 (6)
N20.0263 (7)0.0257 (7)0.0299 (7)0.0099 (6)0.0002 (6)0.0010 (6)
C10.0344 (9)0.0346 (9)0.0433 (10)0.0208 (8)0.0042 (8)0.0016 (8)
C20.0280 (8)0.0268 (8)0.0284 (8)0.0116 (7)−0.0020 (7)−0.0058 (7)
C30.0294 (8)0.0337 (9)0.0423 (10)0.0141 (7)0.0030 (8)−0.0054 (8)
C40.0344 (9)0.0319 (9)0.0413 (10)0.0088 (7)0.0103 (8)−0.0014 (8)
C50.0463 (11)0.0280 (8)0.0348 (10)0.0138 (8)0.0055 (8)0.0025 (7)
C60.0372 (9)0.0299 (8)0.0300 (9)0.0169 (7)−0.0014 (7)−0.0031 (7)
C70.0291 (8)0.0255 (7)0.0243 (8)0.0117 (6)−0.0010 (6)−0.0058 (6)
C80.0303 (8)0.0295 (8)0.0290 (8)0.0163 (7)0.0008 (7)−0.0004 (7)
C90.0321 (8)0.0278 (8)0.0314 (9)0.0143 (7)0.0012 (7)−0.0026 (7)
C100.0293 (8)0.0241 (8)0.0332 (9)0.0106 (6)−0.0004 (7)0.0027 (7)
C110.0307 (9)0.0323 (9)0.0492 (11)0.0127 (7)0.0090 (8)0.0062 (8)
C120.0246 (7)0.0282 (8)0.0324 (9)0.0102 (6)−0.0018 (7)0.0026 (7)
C130.0259 (7)0.0331 (8)0.0292 (9)0.0126 (7)−0.0028 (7)0.0006 (7)
C140.0316 (9)0.0334 (9)0.0422 (10)0.0152 (7)0.0045 (8)0.0038 (8)
C150.0432 (10)0.0385 (10)0.0516 (12)0.0230 (9)0.0000 (9)−0.0032 (9)
C160.0408 (10)0.0552 (12)0.0475 (12)0.0263 (10)0.0019 (9)−0.0101 (10)
C170.0432 (11)0.0513 (12)0.0493 (13)0.0177 (10)0.0186 (10)0.0060 (10)
C180.0424 (10)0.0369 (10)0.0456 (11)0.0157 (8)0.0133 (9)0.0078 (9)
S1—C111.707 (2)C7—C81.512 (2)
S1—C101.7306 (17)C8—C91.525 (2)
N1—C11.460 (2)C8—H8A0.9900
N1—C91.470 (2)C8—H8B0.9900
N1—H1N0.92 (2)C9—C101.501 (2)
N2—C101.297 (2)C9—H91.0000
N2—C121.390 (2)C11—C121.361 (2)
C1—C21.516 (2)C11—H110.9500
C1—H1A0.9900C12—C131.475 (2)
C1—H1B0.9900C13—C141.390 (2)
C2—C71.397 (2)C13—C181.393 (3)
C2—C31.400 (2)C14—C151.389 (3)
C3—C41.380 (3)C14—H140.9500
C3—H30.9500C15—C161.380 (3)
C4—C51.387 (3)C15—H150.9500
C4—H40.9500C16—C171.383 (3)
C5—C61.386 (3)C16—H160.9500
C5—H50.9500C17—C181.372 (3)
C6—C71.396 (2)C17—H170.9500
C6—H60.9500C18—H180.9500
C11—S1—C1089.46 (9)H8A—C8—H8B108.0
C1—N1—C9110.51 (13)N1—C9—C10109.12 (13)
C1—N1—H1N110.0 (13)N1—C9—C8112.02 (13)
C9—N1—H1N106.0 (13)C10—C9—C8112.09 (13)
C10—N2—C12111.30 (14)N1—C9—H9107.8
N1—C1—C2115.29 (14)C10—C9—H9107.8
N1—C1—H1A108.5C8—C9—H9107.8
C2—C1—H1A108.5N2—C10—C9125.27 (15)
N1—C1—H1B108.5N2—C10—S1114.34 (13)
C2—C1—H1B108.5C9—C10—S1120.36 (12)
H1A—C1—H1B107.5C12—C11—S1110.66 (14)
C7—C2—C3119.19 (16)C12—C11—H11124.7
C7—C2—C1120.86 (14)S1—C11—H11124.7
C3—C2—C1119.92 (15)C11—C12—N2114.22 (16)
C4—C3—C2120.90 (17)C11—C12—C13126.56 (16)
C4—C3—H3119.5N2—C12—C13119.21 (14)
C2—C3—H3119.5C14—C13—C18118.28 (17)
C3—C4—C5120.06 (17)C14—C13—C12120.88 (16)
C3—C4—H4120.0C18—C13—C12120.83 (16)
C5—C4—H4120.0C15—C14—C13120.51 (17)
C6—C5—C4119.54 (17)C15—C14—H14119.7
C6—C5—H5120.2C13—C14—H14119.7
C4—C5—H5120.2C16—C15—C14120.46 (19)
C5—C6—C7121.10 (17)C16—C15—H15119.8
C5—C6—H6119.5C14—C15—H15119.8
C7—C6—H6119.5C15—C16—C17119.16 (19)
C6—C7—C2119.21 (15)C15—C16—H16120.4
C6—C7—C8120.20 (15)C17—C16—H16120.4
C2—C7—C8120.58 (15)C18—C17—C16120.65 (19)
C7—C8—C9111.08 (13)C18—C17—H17119.7
C7—C8—H8A109.4C16—C17—H17119.7
C9—C8—H8A109.4C17—C18—C13120.93 (19)
C7—C8—H8B109.4C17—C18—H18119.5
C9—C8—H8B109.4C13—C18—H18119.5
C9—N1—C1—C2−43.4 (2)C8—C9—C10—N219.7 (2)
N1—C1—C2—C712.8 (2)N1—C9—C10—S173.07 (17)
N1—C1—C2—C3−169.22 (16)C8—C9—C10—S1−162.25 (13)
C7—C2—C3—C4−0.7 (3)C11—S1—C10—N20.18 (15)
C1—C2—C3—C4−178.73 (16)C11—S1—C10—C9−178.05 (15)
C2—C3—C4—C50.3 (3)C10—S1—C11—C120.02 (16)
C3—C4—C5—C60.4 (3)S1—C11—C12—N2−0.2 (2)
C4—C5—C6—C7−0.8 (3)S1—C11—C12—C13179.92 (14)
C5—C6—C7—C20.4 (3)C10—N2—C12—C110.3 (2)
C5—C6—C7—C8179.40 (16)C10—N2—C12—C13−179.78 (15)
C3—C2—C7—C60.3 (2)C11—C12—C13—C14178.82 (19)
C1—C2—C7—C6178.32 (16)N2—C12—C13—C14−1.0 (2)
C3—C2—C7—C8−178.67 (15)C11—C12—C13—C18−2.1 (3)
C1—C2—C7—C8−0.6 (2)N2—C12—C13—C18178.05 (16)
C6—C7—C8—C9−160.07 (15)C18—C13—C14—C15−0.3 (3)
C2—C7—C8—C918.9 (2)C12—C13—C14—C15178.84 (17)
C1—N1—C9—C10−171.71 (14)C13—C14—C15—C160.0 (3)
C1—N1—C9—C863.57 (18)C14—C15—C16—C170.1 (3)
C7—C8—C9—N1−50.29 (18)C15—C16—C17—C180.0 (3)
C7—C8—C9—C10−173.34 (13)C16—C17—C18—C13−0.2 (3)
C12—N2—C10—C9177.80 (16)C14—C13—C18—C170.4 (3)
C12—N2—C10—S1−0.32 (18)C12—C13—C18—C17−178.8 (2)
N1—C9—C10—N2−104.95 (19)
D—H···AD—HH···AD···AD—H···A
C11—H11···N1i0.952.543.341 (3)142
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C11—H11⋯N1i0.952.543.341 (3)142

Symmetry code: (i) .

  4 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.  (S)-N-Benzyl-2-methyl-1,2,3,4-tetra-hydro-isoquinoline-3-carboxamide.

Authors:  Tricia Naicker; Thavendran Govender; Hendrik G Kruger; Glenn E M Maguire
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-12-11

3.  (S)-2-Benzyl-N-(2,6-diisopropyl-phen-yl)-1,2,3,4-tetra-hydro-isoquinoline-3-carboxamide.

Authors:  Tricia Naicker; Thavendran Govender; Hendrik G Kruger; Glenn E M Maguire
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-04-13

4.  (1S,3S)-Methyl 2-benzyl-6,7-dimeth-oxy-1-phenyl-1,2,3,4-tetra-hydro-isoquinoline-3-carboxyl-ate.

Authors:  Tricia Naicker; Thavendran Govender; Hendrik G Kruger; Glenn E M Maguire
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-05-14
  4 in total

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