Literature DB >> 22412628

rac-3-[(Anilino)(naphthalen-2-yl)-methyl]thian-4-one.

Klaus Harms, M Saeed Abaee, Mohammad M Mojtahedi, A Wahid Mesbah.   

Abstract

In the title compound, C(22)H(21)NOS, the thio-pyran-one ring adopts a chair-like conformation with the substituent in the axial position. The relative configuration of the racemic compound is 3R,7S according to the numbering scheme used in this publication. In the crystal packing, centrosymmetric dimers are built up via N-H⋯O hydrogen bonds, with graph set R(2) (2)(8).

Entities:  

Year:  2012        PMID： 22412628      PMCID： PMC3295517          DOI： 10.1107/S1600536812005983

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


Related literature

For the preparation and spectroscopic characterization of the title compound and a series of related compounds, see: Abaee et al. (2012 ▶). For the crystal structure of rac-3-[(3-chloro­anilino)(4-chlorophenyl)methyl]thian-4-one, see: Harms et al. (2012 ▶). For the crystal structures of related compounds, see: Guo et al. (2007 ▶); Fun et al. (2009 ▶). For patterns in hydrogen bonding, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C22H21NOS M = 347.46 Monoclinic, a = 10.8049 (10) Å b = 10.5497 (15) Å c = 16.4936 (16) Å β = 97.141 (8)° V = 1865.5 (4) Å3 Z = 4 Mo Kα radiation μ = 0.18 mm−1 T = 193 K 0.45 × 0.45 × 0.36 mm

Data collection

Stoe IPDS I diffractometer Absorption correction: integration [X-AREA and X-RED32 (Stoe & Cie, 2006 ▶)] T min = 0.942, T max = 0.960 13547 measured reflections 3244 independent reflections 1939 reflections with I > 2σ(I) R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.033 wR(F 2) = 0.074 S = 0.79 3244 reflections 230 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.23 e Å−3 Δρmin = −0.37 e Å−3 Data collection: EXPOSE (Stoe & Cie, 1994 ▶); cell refinement: CELL (Stoe & Cie, 1994 ▶); data reduction: X-RED32 (Stoe & Cie, 2006 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2007 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶), PLATON (Spek, 2009 ▶), and WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812005983/fj2509sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005983/fj2509Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812005983/fj2509Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C22H21NOSF(000) = 736
Mr = 347.46Dx = 1.237 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7999 reflections
a = 10.8049 (10) Åθ = 2.3–26.0°
b = 10.5497 (15) ŵ = 0.18 mm−1
c = 16.4936 (16) ÅT = 193 K
β = 97.141 (8)°Nugget, colourless
V = 1865.5 (4) Å30.45 × 0.45 × 0.36 mm
Z = 4
Stoe IPDS I diffractometer3244 independent reflections
Radiation source: fine-focus sealed tube1939 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
Detector resolution: 6.67 pixels mm-1θmax = 25.4°, θmin = 2.1°
rotation method scansh = −13→12
Absorption correction: integration [X-AREA and X-RED32 (Stoe & Cie, 2006)]k = −12→12
Tmin = 0.942, Tmax = 0.960l = −19→19
13547 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074H atoms treated by a mixture of independent and constrained refinement
S = 0.79w = 1/[σ2(Fo2) + (0.0399P)2] where P = (Fo2 + 2Fc2)/3
3244 reflections(Δ/σ)max < 0.001
230 parametersΔρmax = 0.23 e Å−3
0 restraintsΔρmin = −0.37 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
S10.06564 (5)0.68462 (6)0.53056 (4)0.0733 (2)
O10.38884 (11)0.55992 (11)0.42256 (7)0.0481 (3)
N80.48932 (11)0.69693 (12)0.59618 (8)0.0318 (3)
H80.5282 (14)0.6206 (15)0.5880 (10)0.033 (4)*
C20.16654 (16)0.55096 (17)0.55576 (14)0.0568 (6)
H2A0.15840.52370.61230.068*
H2B0.13860.47980.51880.068*
C30.30417 (14)0.57832 (15)0.54910 (11)0.0359 (4)
H30.35170.49770.56110.043*
C40.32089 (15)0.61845 (15)0.46296 (11)0.0381 (4)
C50.24585 (19)0.72936 (18)0.42754 (13)0.0579 (6)
H5A0.26180.74240.37030.070*
H5B0.27280.80670.45880.070*
C60.1050 (2)0.7089 (2)0.42969 (16)0.0808 (8)
H6A0.07760.63440.39560.097*
H6B0.05910.78380.40550.097*
C70.36003 (13)0.67883 (14)0.61120 (10)0.0301 (4)
H70.31410.76030.59910.036*
C90.56671 (14)0.78247 (14)0.64329 (10)0.0306 (4)
C100.52229 (16)0.89433 (15)0.67309 (11)0.0414 (4)
H100.43540.91180.66560.050*
C110.60450 (18)0.98055 (17)0.71379 (12)0.0519 (5)
H110.57311.05740.73330.062*
C120.73045 (18)0.95712 (18)0.72650 (13)0.0542 (5)
H120.78601.01720.75410.065*
C130.77470 (17)0.84535 (18)0.69860 (12)0.0494 (5)
H130.86150.82750.70780.059*
C140.69458 (15)0.75867 (16)0.65734 (11)0.0396 (4)
H140.72680.68190.63830.047*
C150.34684 (14)0.64065 (13)0.69838 (10)0.0309 (4)
C160.25886 (15)0.69614 (14)0.74005 (11)0.0362 (4)
H160.20720.76090.71410.043*
C170.24295 (15)0.65944 (15)0.82070 (11)0.0358 (4)
C180.14989 (17)0.71312 (17)0.86377 (12)0.0484 (5)
H180.09650.77720.83860.058*
C190.1364 (2)0.67372 (18)0.94068 (12)0.0561 (6)
H190.07300.70990.96850.067*
C200.21464 (19)0.58064 (17)0.97926 (12)0.0551 (6)
H200.20390.55381.03290.066*
C210.30610 (18)0.52812 (16)0.94044 (11)0.0457 (5)
H210.35970.46600.96770.055*
C220.32231 (15)0.56508 (14)0.85973 (11)0.0353 (4)
C230.41391 (15)0.51076 (15)0.81611 (11)0.0385 (4)
H230.46860.44810.84170.046*
C240.42500 (14)0.54655 (14)0.73845 (11)0.0354 (4)
H240.48660.50760.71040.042*
U11U22U33U12U13U23
S10.0349 (2)0.0790 (4)0.1041 (6)−0.0052 (3)0.0016 (3)−0.0435 (4)
O10.0546 (7)0.0537 (7)0.0350 (8)0.0127 (6)0.0011 (7)−0.0116 (6)
N80.0310 (7)0.0330 (7)0.0325 (9)−0.0052 (6)0.0084 (6)−0.0056 (6)
C20.0460 (11)0.0515 (11)0.0727 (16)−0.0199 (9)0.0067 (11)−0.0201 (10)
C30.0378 (9)0.0311 (8)0.0383 (12)−0.0046 (7)0.0032 (8)−0.0072 (7)
C40.0410 (9)0.0359 (9)0.0348 (12)−0.0004 (8)−0.0054 (9)−0.0129 (8)
C50.0824 (14)0.0510 (11)0.0378 (13)0.0241 (10)−0.0030 (11)−0.0043 (9)
C60.0664 (14)0.0796 (16)0.085 (2)0.0312 (12)−0.0363 (13)−0.0339 (14)
C70.0305 (8)0.0311 (8)0.0293 (10)−0.0030 (7)0.0062 (7)−0.0028 (7)
C90.0353 (8)0.0343 (8)0.0222 (10)−0.0076 (7)0.0031 (8)0.0042 (7)
C100.0392 (9)0.0390 (9)0.0449 (13)−0.0053 (8)0.0005 (9)−0.0058 (8)
C110.0577 (12)0.0432 (10)0.0518 (15)−0.0085 (9)−0.0048 (11)−0.0117 (9)
C120.0549 (12)0.0532 (12)0.0490 (15)−0.0191 (10)−0.0154 (10)−0.0005 (10)
C130.0380 (9)0.0556 (12)0.0508 (14)−0.0110 (9)−0.0100 (9)0.0116 (10)
C140.0399 (9)0.0402 (9)0.0379 (12)−0.0031 (8)0.0022 (9)0.0073 (8)
C150.0303 (8)0.0294 (8)0.0337 (11)−0.0061 (7)0.0067 (8)−0.0040 (7)
C160.0391 (8)0.0338 (9)0.0364 (12)0.0022 (7)0.0077 (8)−0.0008 (8)
C170.0424 (9)0.0331 (9)0.0336 (11)−0.0021 (7)0.0118 (9)−0.0048 (7)
C180.0591 (11)0.0453 (10)0.0440 (13)0.0128 (9)0.0188 (10)−0.0016 (9)
C190.0763 (14)0.0537 (11)0.0440 (14)0.0113 (11)0.0299 (12)−0.0060 (10)
C200.0856 (15)0.0481 (11)0.0354 (12)0.0026 (11)0.0228 (12)−0.0021 (9)
C210.0627 (12)0.0381 (9)0.0371 (12)0.0003 (9)0.0097 (10)−0.0001 (8)
C220.0419 (9)0.0314 (8)0.0336 (11)−0.0044 (7)0.0082 (8)−0.0027 (7)
C230.0382 (9)0.0347 (9)0.0432 (13)0.0030 (7)0.0078 (9)0.0023 (8)
C240.0325 (8)0.0356 (9)0.0398 (12)0.0012 (7)0.0114 (8)0.0000 (8)
S1—C61.786 (3)C11—H110.9500
S1—C21.799 (2)C12—C131.373 (3)
O1—C41.2190 (18)C12—H120.9500
N8—C91.398 (2)C13—C141.379 (2)
N8—C71.4614 (18)C13—H130.9500
N8—H80.926 (15)C14—H140.9500
C2—C31.532 (2)C15—C161.372 (2)
C2—H2A0.9900C15—C241.413 (2)
C2—H2B0.9900C16—C171.416 (2)
C3—C41.515 (2)C16—H160.9500
C3—C71.544 (2)C17—C221.415 (2)
C3—H31.0000C17—C181.419 (2)
C4—C51.500 (2)C18—C191.360 (3)
C5—C61.542 (3)C18—H180.9500
C5—H5A0.9900C19—C201.397 (3)
C5—H5B0.9900C19—H190.9500
C6—H6A0.9900C20—C211.361 (2)
C6—H6B0.9900C20—H200.9500
C7—C151.517 (2)C21—C221.419 (2)
C7—H71.0000C21—H210.9500
C9—C101.387 (2)C22—C231.415 (2)
C9—C141.395 (2)C23—C241.355 (2)
C10—C111.385 (2)C23—H230.9500
C10—H100.9500C24—H240.9500
C11—C121.373 (3)
C6—S1—C296.89 (10)C12—C11—C10121.29 (18)
C9—N8—C7120.55 (12)C12—C11—H11119.4
C9—N8—H8113.1 (10)C10—C11—H11119.4
C7—N8—H8111.8 (9)C13—C12—C11118.89 (17)
C3—C2—S1113.67 (13)C13—C12—H12120.6
C3—C2—H2A108.8C11—C12—H12120.6
S1—C2—H2A108.8C12—C13—C14120.76 (17)
C3—C2—H2B108.8C12—C13—H13119.6
S1—C2—H2B108.8C14—C13—H13119.6
H2A—C2—H2B107.7C13—C14—C9120.70 (16)
C4—C3—C2110.49 (16)C13—C14—H14119.7
C4—C3—C7110.36 (12)C9—C14—H14119.7
C2—C3—C7112.62 (13)C16—C15—C24118.46 (15)
C4—C3—H3107.7C16—C15—C7120.95 (14)
C2—C3—H3107.7C24—C15—C7120.59 (13)
C7—C3—H3107.7C15—C16—C17121.78 (15)
O1—C4—C5121.02 (17)C15—C16—H16119.1
O1—C4—C3121.42 (15)C17—C16—H16119.1
C5—C4—C3117.49 (15)C22—C17—C16118.82 (14)
C4—C5—C6111.66 (17)C22—C17—C18118.67 (16)
C4—C5—H5A109.3C16—C17—C18122.51 (16)
C6—C5—H5A109.3C19—C18—C17120.67 (17)
C4—C5—H5B109.3C19—C18—H18119.7
C6—C5—H5B109.3C17—C18—H18119.7
H5A—C5—H5B107.9C18—C19—C20120.71 (17)
C5—C6—S1113.05 (16)C18—C19—H19119.6
C5—C6—H6A109.0C20—C19—H19119.6
S1—C6—H6A109.0C21—C20—C19120.40 (18)
C5—C6—H6B109.0C21—C20—H20119.8
S1—C6—H6B109.0C19—C20—H20119.8
H6A—C6—H6B107.8C20—C21—C22120.76 (18)
N8—C7—C15113.57 (13)C20—C21—H21119.6
N8—C7—C3106.28 (12)C22—C21—H21119.6
C15—C7—C3111.80 (12)C23—C22—C17118.42 (15)
N8—C7—H7108.3C23—C22—C21122.78 (16)
C15—C7—H7108.3C17—C22—C21118.79 (15)
C3—C7—H7108.3C24—C23—C22121.16 (15)
C10—C9—C14118.27 (15)C24—C23—H23119.4
C10—C9—N8122.46 (14)C22—C23—H23119.4
C14—C9—N8119.17 (14)C23—C24—C15121.34 (14)
C11—C10—C9120.08 (16)C23—C24—H24119.3
C11—C10—H10120.0C15—C24—H24119.3
C9—C10—H10120.0
C6—S1—C2—C357.57 (16)N8—C9—C14—C13175.40 (15)
S1—C2—C3—C4−59.40 (17)N8—C7—C15—C16135.46 (15)
S1—C2—C3—C764.52 (19)C3—C7—C15—C16−104.28 (16)
C2—C3—C4—O1−121.46 (17)N8—C7—C15—C24−44.72 (19)
C7—C3—C4—O1113.33 (16)C3—C7—C15—C2475.54 (18)
C2—C3—C4—C555.62 (19)C24—C15—C16—C17−1.5 (2)
C7—C3—C4—C5−69.58 (19)C7—C15—C16—C17178.33 (14)
O1—C4—C5—C6121.38 (19)C15—C16—C17—C221.6 (2)
C3—C4—C5—C6−55.7 (2)C15—C16—C17—C18−178.03 (16)
C4—C5—C6—S159.1 (2)C22—C17—C18—C19−0.7 (3)
C2—S1—C6—C5−56.56 (16)C16—C17—C18—C19178.91 (18)
C9—N8—C7—C15−56.27 (19)C17—C18—C19—C200.7 (3)
C9—N8—C7—C3−179.60 (14)C18—C19—C20—C210.2 (3)
C4—C3—C7—N8−54.62 (17)C19—C20—C21—C22−1.1 (3)
C2—C3—C7—N8−178.61 (15)C16—C17—C22—C23−0.4 (2)
C4—C3—C7—C15−179.05 (13)C18—C17—C22—C23179.22 (15)
C2—C3—C7—C1556.96 (19)C16—C17—C22—C21−179.83 (15)
C7—N8—C9—C10−34.1 (2)C18—C17—C22—C21−0.2 (2)
C7—N8—C9—C14149.59 (15)C20—C21—C22—C23−178.28 (17)
C14—C9—C10—C111.6 (2)C20—C21—C22—C171.1 (3)
N8—C9—C10—C11−174.77 (16)C17—C22—C23—C24−0.8 (2)
C9—C10—C11—C12−0.8 (3)C21—C22—C23—C24178.61 (17)
C10—C11—C12—C13−0.5 (3)C22—C23—C24—C150.9 (2)
C11—C12—C13—C141.0 (3)C16—C15—C24—C230.3 (2)
C12—C13—C14—C9−0.2 (3)C7—C15—C24—C23−179.57 (15)
C10—C9—C14—C13−1.1 (2)
D—H···AD—HH···AD···AD—H···A
N8—H8···O1i0.926 (15)2.121 (16)3.0450 (18)175.4 (13)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N8—H8⋯O1i0.926 (15)2.121 (16)3.0450 (18)175.4 (13)

Symmetry code: (i) .

  5 in total

1.  Chiral Brønsted acid-catalyzed direct asymmetric Mannich reaction.

Authors:  Qi-Xiang Guo; Hua Liu; Chang Guo; Shi-Wei Luo; Yi Gu; Liu-Zhu Gong
Journal:  J Am Chem Soc       Date:  2007-03-15       Impact factor: 15.419

2.  A short history of SHELX.

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

3.  2-[(4-tert-Butyl-anilino)(phen-yl)meth-yl]cyclo-hexa-none.

Authors:  Hoong-Kun Fun; Suchada Chantrapromma; Sankappa Rai; Prakash Shetty; Arun M Isloor
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-02-18

4.  rac-3-[(3-Chloro-anilino)(4-chloro-phenyl)meth-yl]thian-4-one.

Authors:  Klaus Harms; M Saeed Abaee; Mohammad M Mojtahedi; A Wahid Mesbah
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-02-10

5.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  5 in total
  1 in total

1.  rac-3-[(3-Chloro-anilino)(4-chloro-phenyl)meth-yl]thian-4-one.

Authors:  Klaus Harms; M Saeed Abaee; Mohammad M Mojtahedi; A Wahid Mesbah
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-02-10
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.