Literature DB >> 21581870

1-(4-Chloro-phen-yl)-2-[(3-phenyl-isoquinolin-1-yl)sulfan-yl]ethanone.

P Manivel, Venkatesha R Hathwar, P Nithya, R Subashini, F Nawaz Khan.   

Abstract

The title compound, C(23)H(16)ClNOS, exhibits dihedral angles of 11.73 (1) and 66.07 (1)°, respectively, between the mean plane of the isoquinoline system and the attached phenyl ring, and between the isoquinoline system and the chloro-phenyl ring. The dihedral angle between the phenyl and chlorophenyl rings is 54.66 (1)°.

Entities:  

Year:  2009        PMID： 21581870      PMCID： PMC2968208          DOI： 10.1107/S1600536809000257

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


Related literature

For general background, see: Cremlyn et al. (1996 ▶); Carreno (1995 ▶); Kondo et al. (2000 ▶); Mosberg & Omnaas (1985 ▶); McReynolds et al. (2004 ▶). For related crystal structures, see: Hathwar et al. (2008 ▶); Manivel et al. (2009 ▶).

Experimental

Crystal data

C23H16ClNOS M = 389.89 Orthorhombic, a = 9.5874 (14) Å b = 17.888 (3) Å c = 22.025 (3) Å V = 3777.3 (10) Å3 Z = 8 Mo Kα radiation μ = 0.33 mm−1 T = 290 (2) K 0.26 × 0.20 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.901, T max = 0.956 25674 measured reflections 3332 independent reflections 1915 reflections with I > 2σ(I) R int = 0.116

Refinement

R[F 2 > 2σ(F 2)] = 0.071 wR(F 2) = 0.125 S = 1.04 3332 reflections 244 parameters H-atom parameters constrained Δρmax = 0.23 e Å−3 Δρmin = −0.23 e Å−3 Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809000257/ng2532sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000257/ng2532Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C23H16ClNOSF(000) = 1616
Mr = 389.89Dx = 1.371 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 871 reflections
a = 9.5874 (14) Åθ = 1.9–25.0°
b = 17.888 (3) ŵ = 0.33 mm−1
c = 22.025 (3) ÅT = 290 K
V = 3777.3 (10) Å3Rod, colourless
Z = 80.26 × 0.20 × 0.14 mm
Bruker SMART CCD area-detector diffractometer3332 independent reflections
Radiation source: fine-focus sealed tube1915 reflections with I > 2σ(I)
graphiteRint = 0.116
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.901, Tmax = 0.956k = −21→21
25674 measured reflectionsl = −24→26
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0308P)2 + 0.7191P] where P = (Fo2 + 2Fc2)/3
3332 reflections(Δ/σ)max < 0.001
244 parametersΔρmax = 0.23 e Å−3
0 restraintsΔρmin = −0.23 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
Cl1−0.16890 (17)0.07371 (9)0.25163 (6)0.1375 (6)
S1−0.09127 (10)0.34062 (5)−0.06818 (5)0.0545 (3)
O10.0295 (2)0.19469 (13)−0.02148 (12)0.0588 (7)
N10.0851 (3)0.36685 (14)0.02265 (13)0.0406 (7)
C10.0416 (3)0.39062 (18)−0.03051 (16)0.0401 (9)
C20.1941 (3)0.40302 (18)0.05067 (15)0.0390 (9)
C30.2597 (4)0.46147 (19)0.02355 (16)0.0460 (9)
H30.33480.48410.04300.055*
C40.2805 (4)0.54850 (19)−0.06405 (19)0.0554 (10)
H40.35640.5724−0.04630.067*
C50.2337 (5)0.5720 (2)−0.1189 (2)0.0644 (12)
H50.27840.6111−0.13870.077*
C60.1184 (5)0.5375 (2)−0.14581 (18)0.0665 (12)
H60.08620.5543−0.18320.080*
C70.0532 (4)0.47981 (19)−0.11778 (17)0.0570 (11)
H7−0.02370.4575−0.13600.068*
C80.1007 (4)0.45349 (17)−0.06155 (16)0.0410 (8)
C90.2160 (4)0.48838 (17)−0.03338 (16)0.0428 (9)
C100.2362 (4)0.3727 (2)0.11049 (16)0.0439 (9)
C110.3618 (4)0.3927 (2)0.13781 (17)0.0656 (12)
H110.42010.42670.11840.079*
C120.4012 (5)0.3632 (3)0.19275 (19)0.0801 (13)
H120.48540.37790.21000.096*
C130.3193 (5)0.3129 (3)0.22247 (19)0.0778 (13)
H130.34630.29330.25980.093*
C140.1957 (5)0.2919 (2)0.19589 (19)0.0748 (13)
H140.13900.25700.21520.090*
C150.1543 (4)0.3218 (2)0.14102 (17)0.0594 (11)
H150.06940.30720.12430.071*
C16−0.1538 (3)0.28339 (18)−0.00757 (16)0.0486 (10)
H16A−0.16850.31500.02760.058*
H16B−0.24400.2634−0.01930.058*
C17−0.0618 (4)0.21887 (18)0.01117 (18)0.0454 (10)
C18−0.0910 (4)0.18457 (17)0.07171 (18)0.0470 (9)
C19−0.2116 (4)0.1996 (2)0.10416 (18)0.0529 (10)
H19−0.27670.23300.08850.064*
C20−0.2360 (4)0.1656 (3)0.15937 (19)0.0693 (12)
H20−0.31790.17540.18060.083*
C21−0.1389 (6)0.1174 (3)0.18275 (19)0.0769 (13)
C22−0.0177 (5)0.1022 (2)0.1514 (2)0.0762 (13)
H220.04800.06950.16750.091*
C230.0055 (4)0.1354 (2)0.0962 (2)0.0630 (11)
H230.08690.12490.07500.076*
U11U22U33U12U13U23
Cl10.1541 (14)0.1891 (16)0.0694 (9)−0.0056 (13)−0.0200 (9)0.0362 (10)
S10.0462 (6)0.0542 (5)0.0632 (7)−0.0085 (5)−0.0116 (6)−0.0032 (5)
O10.0391 (15)0.0504 (15)0.087 (2)0.0030 (12)0.0112 (15)−0.0136 (14)
N10.0357 (17)0.0379 (15)0.0481 (19)−0.0030 (14)0.0007 (16)−0.0072 (14)
C10.032 (2)0.038 (2)0.050 (2)0.0031 (16)0.0014 (18)−0.0074 (18)
C20.036 (2)0.037 (2)0.045 (2)0.0020 (17)0.0029 (17)−0.0125 (17)
C30.044 (2)0.040 (2)0.054 (2)−0.0063 (17)−0.005 (2)−0.0126 (19)
C40.055 (3)0.040 (2)0.071 (3)−0.0047 (19)0.010 (2)−0.005 (2)
C50.074 (3)0.043 (2)0.076 (3)−0.001 (2)0.017 (3)0.006 (2)
C60.084 (3)0.058 (3)0.058 (3)0.005 (2)0.003 (3)0.011 (2)
C70.060 (3)0.048 (2)0.063 (3)0.000 (2)−0.004 (2)0.003 (2)
C80.042 (2)0.0353 (18)0.046 (2)0.0077 (17)0.0068 (19)−0.0053 (18)
C90.043 (2)0.0303 (19)0.055 (2)−0.0010 (17)0.007 (2)−0.0096 (18)
C100.040 (2)0.047 (2)0.045 (2)−0.0009 (18)0.001 (2)−0.0121 (19)
C110.057 (3)0.087 (3)0.054 (3)−0.015 (2)−0.002 (2)0.004 (2)
C120.064 (3)0.119 (4)0.057 (3)−0.018 (3)−0.013 (3)0.003 (3)
C130.082 (4)0.101 (4)0.050 (3)−0.005 (3)−0.010 (3)0.006 (3)
C140.084 (3)0.078 (3)0.063 (3)−0.016 (3)−0.009 (3)0.019 (3)
C150.060 (3)0.059 (3)0.058 (3)−0.009 (2)−0.011 (2)0.005 (2)
C160.033 (2)0.044 (2)0.068 (3)−0.0058 (17)−0.0008 (19)−0.0072 (19)
C170.031 (2)0.0346 (19)0.071 (3)−0.0067 (17)−0.005 (2)−0.011 (2)
C180.039 (2)0.0350 (18)0.067 (3)−0.0037 (18)−0.005 (2)−0.012 (2)
C190.047 (3)0.053 (2)0.058 (3)−0.002 (2)−0.008 (2)−0.008 (2)
C200.059 (3)0.091 (3)0.058 (3)−0.009 (3)−0.006 (3)−0.013 (3)
C210.084 (4)0.090 (3)0.057 (3)−0.012 (3)−0.019 (3)−0.003 (3)
C220.077 (4)0.062 (3)0.090 (4)0.004 (3)−0.030 (3)0.007 (3)
C230.050 (3)0.050 (2)0.089 (3)0.002 (2)−0.008 (2)−0.001 (2)
Cl1—C211.731 (4)C11—C121.373 (5)
S1—C11.764 (3)C11—H110.9300
S1—C161.786 (3)C12—C131.362 (5)
O1—C171.212 (4)C12—H120.9300
N1—C11.314 (4)C13—C141.374 (5)
N1—C21.375 (4)C13—H130.9300
C1—C81.433 (4)C14—C151.379 (5)
C2—C31.359 (4)C14—H140.9300
C2—C101.481 (4)C15—H150.9300
C3—C91.407 (4)C16—C171.510 (4)
C3—H30.9300C16—H16A0.9700
C4—C51.355 (5)C16—H16B0.9700
C4—C91.412 (4)C17—C181.494 (5)
C4—H40.9300C18—C231.385 (5)
C5—C61.398 (5)C18—C191.385 (5)
C5—H50.9300C19—C201.380 (5)
C6—C71.355 (5)C19—H190.9300
C6—H60.9300C20—C211.369 (6)
C7—C81.401 (4)C20—H200.9300
C7—H70.9300C21—C221.380 (6)
C8—C91.413 (4)C22—C231.371 (5)
C10—C151.378 (4)C22—H220.9300
C10—C111.392 (5)C23—H230.9300
C1—S1—C16100.46 (17)C11—C12—H12119.4
C1—N1—C2119.3 (3)C12—C13—C14118.2 (4)
N1—C1—C8123.6 (3)C12—C13—H13120.9
N1—C1—S1119.0 (3)C14—C13—H13120.9
C8—C1—S1117.3 (3)C13—C14—C15121.0 (4)
C3—C2—N1121.1 (3)C13—C14—H14119.5
C3—C2—C10123.1 (3)C15—C14—H14119.5
N1—C2—C10115.8 (3)C10—C15—C14121.3 (4)
C2—C3—C9121.2 (3)C10—C15—H15119.4
C2—C3—H3119.4C14—C15—H15119.4
C9—C3—H3119.4C17—C16—S1116.5 (2)
C5—C4—C9121.1 (4)C17—C16—H16A108.2
C5—C4—H4119.4S1—C16—H16A108.2
C9—C4—H4119.4C17—C16—H16B108.2
C4—C5—C6120.3 (4)S1—C16—H16B108.2
C4—C5—H5119.9H16A—C16—H16B107.3
C6—C5—H5119.9O1—C17—C18121.2 (3)
C7—C6—C5120.5 (4)O1—C17—C16122.2 (3)
C7—C6—H6119.8C18—C17—C16116.6 (3)
C5—C6—H6119.8C23—C18—C19118.6 (4)
C6—C7—C8120.6 (4)C23—C18—C17118.9 (4)
C6—C7—H7119.7C19—C18—C17122.5 (3)
C8—C7—H7119.7C20—C19—C18120.7 (4)
C7—C8—C9119.6 (3)C20—C19—H19119.6
C7—C8—C1123.8 (3)C18—C19—H19119.6
C9—C8—C1116.5 (3)C21—C20—C19119.6 (4)
C3—C9—C4123.8 (3)C21—C20—H20120.2
C3—C9—C8118.2 (3)C19—C20—H20120.2
C4—C9—C8118.0 (3)C20—C21—C22120.6 (4)
C15—C10—C11116.9 (4)C20—C21—Cl1120.1 (4)
C15—C10—C2121.4 (3)C22—C21—Cl1119.3 (4)
C11—C10—C2121.8 (3)C23—C22—C21119.7 (4)
C12—C11—C10121.3 (4)C23—C22—H22120.2
C12—C11—H11119.3C21—C22—H22120.2
C10—C11—H11119.3C22—C23—C18120.8 (4)
C13—C12—C11121.3 (4)C22—C23—H23119.6
C13—C12—H12119.4C18—C23—H23119.6
C2—N1—C1—C8−0.6 (4)C3—C2—C10—C11−12.3 (5)
C2—N1—C1—S1176.3 (2)N1—C2—C10—C11165.9 (3)
C16—S1—C1—N114.4 (3)C15—C10—C11—C12−0.4 (6)
C16—S1—C1—C8−168.5 (2)C2—C10—C11—C12−178.8 (4)
C1—N1—C2—C3−1.8 (4)C10—C11—C12—C130.4 (7)
C1—N1—C2—C10179.9 (3)C11—C12—C13—C140.3 (7)
N1—C2—C3—C91.8 (5)C12—C13—C14—C15−1.0 (7)
C10—C2—C3—C9180.0 (3)C11—C10—C15—C14−0.3 (6)
C9—C4—C5—C61.0 (6)C2—C10—C15—C14178.1 (3)
C4—C5—C6—C7−0.8 (6)C13—C14—C15—C101.0 (6)
C5—C6—C7—C8−0.3 (6)C1—S1—C16—C17−73.9 (3)
C6—C7—C8—C91.2 (5)S1—C16—C17—O1−18.5 (4)
C6—C7—C8—C1−176.9 (3)S1—C16—C17—C18163.1 (2)
N1—C1—C8—C7−178.9 (3)O1—C17—C18—C2313.8 (5)
S1—C1—C8—C74.2 (4)C16—C17—C18—C23−167.7 (3)
N1—C1—C8—C92.9 (5)O1—C17—C18—C19−165.7 (3)
S1—C1—C8—C9−174.0 (2)C16—C17—C18—C1912.8 (4)
C2—C3—C9—C4−179.5 (3)C23—C18—C19—C20−0.8 (5)
C2—C3—C9—C80.7 (5)C17—C18—C19—C20178.7 (3)
C5—C4—C9—C3−180.0 (3)C18—C19—C20—C211.0 (6)
C5—C4—C9—C8−0.2 (5)C19—C20—C21—C22−0.5 (6)
C7—C8—C9—C3178.9 (3)C19—C20—C21—Cl1−179.4 (3)
C1—C8—C9—C3−2.8 (4)C20—C21—C22—C23−0.2 (6)
C7—C8—C9—C4−0.9 (4)Cl1—C21—C22—C23178.7 (3)
C1—C8—C9—C4177.3 (3)C21—C22—C23—C180.4 (6)
C3—C2—C10—C15169.4 (3)C19—C18—C23—C220.1 (5)
N1—C2—C10—C15−12.4 (4)C17—C18—C23—C22−179.4 (3)
D—H···AD—HH···AD···AD—H···A
C4—H4···O1i0.932.513.322 (4)147
C16—H16B···O1ii0.972.473.128 (4)125
  5 in total

1.  Metal-catalyzed carbon-sulfur bond formation.

Authors:  T Kondo; T A Mitsudo Ta
Journal:  Chem Rev       Date:  2000-08-09       Impact factor: 60.622

Review 2.  Synthesis of phosphorus and sulfur heterocycles via ring-closing olefin metathesis.

Authors:  Matthew D McReynolds; Joseph M Dougherty; Paul R Hanson
Journal:  Chem Rev       Date:  2004-05       Impact factor: 60.622

3.  A short history of SHELX.

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

4.  3-Phenyl-1-[2-(3-phenyl-isoquinolin-1-yl)-diselan-yl]isoquinoline.

Authors:  Venkatesha R Hathwar; K Prabakaran; R Subashini; P Manivel; F Nawaz Khan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-11-08

5.  1-(3-Phenyl-isoquinolin-1-yl)hydrazine.

Authors:  P Manivel; Venkatesha R Hathwar; P Nithya; K Prabakaran; F Nawaz Khan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-12-17
  5 in total
  1 in total

1.  1-(4-Chloro-3-fluoro-phen-yl)-2-[(3-phenyl-isoquinolin-1-yl)sulfan-yl]ethanone.

Authors:  P Manivel; Venkatesha R Hathwar; T Maiyalagan; N Burcu Arslan; F Nawaz Khan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-01-17
  1 in total

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