Literature DB >> 21579373

4-Methoxy-benzene-carbothio-amide.

Saqib Ali, Shahid Hameed, Ahmad Luqman, Tashfeen Akhtar, Masood Parvez.   

Abstract

The asymmetric unit of the title compound, C(8)H(9)NOS, contains two independent mol-ecules with the meth-oxy groups oriented in opposite conformations. The mean planes of the carbothio-amide groups are tilted by 7.88 (15) and 11.16 (9)° from the mean planes of the benzene rings. In the crystal, the mol-ecules form dimers via intermolecular N-H⋯S inter-molecular hydrogen bonds, resulting in eight-membered rings of R(2) (2)(8) graph-set motif. The dimers are further linked by C-H⋯O hydrogen bonds into chains along the c axis. Adjacent chains inter-act through inter-molecular N-H⋯S hydrogen bonds, generating eight-membered rings of R(4) (2)(8) graph-set motif.

Entities:  

Year:  2010        PMID： 21579373      PMCID： PMC2979506          DOI： 10.1107/S1600536810015825

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


Related literature

For the synthesis, biological activity and applications of thio­amides, see: Zahid et al. (2009 ▶); Klimesova et al. (1999 ▶); Jagodzinski (2003 ▶); Lebana et al. (2008 ▶). For related structures, see: Khan et al. (2009a ▶,b ▶,c ▶); Jian et al. (2006 ▶). For graph-set notation, see: Bernstein et al. (1994 ▶).

Experimental

Crystal data

C8H9NOS M = 167.22 Orthorhombic, a = 5.6545 (2) Å b = 7.3966 (2) Å c = 38.7497 (13) Å V = 1620.67 (9) Å3 Z = 8 Mo Kα radiation μ = 0.34 mm−1 T = 173 K 0.12 × 0.10 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.961, T max = 0.974 6598 measured reflections 3656 independent reflections 3500 reflections with I > 2σ(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.033 wR(F 2) = 0.078 S = 1.09 3656 reflections 213 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.22 e Å−3 Δρmin = −0.27 e Å−3 Absolute structure: Flack (1983 ▶), 1469 Friedel pairs Flack parameter: 0.03 (7) Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810015825/rz2437sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015825/rz2437Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C8H9NOSF(000) = 704
Mr = 167.22Dx = 1.371 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3578 reflections
a = 5.6545 (2) Åθ = 1.0–27.5°
b = 7.3966 (2) ŵ = 0.34 mm−1
c = 38.7497 (13) ÅT = 173 K
V = 1620.67 (9) Å3Prism, yellow
Z = 80.12 × 0.10 × 0.08 mm
Nonius KappaCCD diffractometer3656 independent reflections
Radiation source: fine-focus sealed tube3500 reflections with I > 2σ(I)
graphiteRint = 0.025
ω and φ scansθmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)h = −6→7
Tmin = 0.961, Tmax = 0.974k = −9→9
6598 measured reflectionsl = −50→49
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.078w = 1/[σ2(Fo2) + (0.0226P)2 + 0.7048P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
3656 reflectionsΔρmax = 0.22 e Å−3
213 parametersΔρmin = −0.27 e Å−3
0 restraintsAbsolute structure: Flack (1983), 1469 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.03 (7)
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
S10.54377 (9)0.80205 (8)0.411169 (12)0.03778 (14)
S110.00254 (9)0.83920 (9)0.329665 (12)0.04206 (15)
O10.3345 (2)1.12722 (19)0.56954 (3)0.0314 (3)
O110.2829 (2)0.8073 (2)0.16293 (3)0.0372 (3)
N10.1172 (3)0.9318 (3)0.41309 (5)0.0384 (4)
H1A−0.015 (5)0.958 (3)0.4224 (6)0.046*
H1B0.109 (4)0.901 (3)0.3904 (7)0.046*
N110.4395 (3)0.7318 (3)0.32528 (4)0.0380 (4)
H11A0.445 (4)0.734 (3)0.3477 (6)0.046*
H11B0.577 (4)0.720 (3)0.3147 (6)0.046*
C10.3167 (3)0.9530 (2)0.46743 (4)0.0215 (3)
C20.5056 (3)0.9037 (2)0.48859 (4)0.0233 (3)
H20.62950.83210.47920.028*
C30.5173 (3)0.9561 (2)0.52284 (4)0.0245 (3)
H30.64810.92110.53670.029*
C40.3364 (3)1.0602 (2)0.53680 (5)0.0247 (4)
C50.1422 (3)1.1069 (2)0.51645 (5)0.0274 (4)
H50.01641.17530.52610.033*
C60.1329 (3)1.0540 (2)0.48245 (5)0.0250 (4)
H6−0.00031.08630.46880.030*
C70.3124 (3)0.9001 (2)0.43058 (5)0.0240 (4)
C80.5271 (4)1.0780 (3)0.59156 (5)0.0432 (5)
H8A0.52970.94640.59450.065*
H8B0.50731.13600.61410.065*
H8C0.67621.11780.58120.065*
C110.2594 (3)0.7796 (2)0.26992 (4)0.0223 (3)
C120.0790 (3)0.8599 (2)0.25047 (5)0.0272 (4)
H12−0.05370.91120.26190.033*
C130.0917 (3)0.8656 (3)0.21488 (5)0.0292 (4)
H13−0.03190.92060.20200.035*
C140.2848 (3)0.7913 (3)0.19784 (5)0.0274 (4)
C150.4646 (3)0.7085 (2)0.21656 (4)0.0286 (4)
H150.59570.65570.20500.034*
C160.4502 (3)0.7039 (2)0.25229 (4)0.0272 (4)
H160.57340.64780.26510.033*
C170.2475 (3)0.7799 (2)0.30819 (5)0.0256 (4)
C180.4835 (5)0.7421 (4)0.14431 (5)0.0517 (6)
H18A0.62670.80170.15290.078*
H18B0.46380.76880.11970.078*
H18C0.49760.61120.14760.078*
U11U22U33U12U13U23
S10.0264 (2)0.0619 (3)0.0250 (2)0.0131 (2)−0.00098 (18)−0.0060 (2)
S110.0233 (2)0.0758 (4)0.0271 (2)0.0073 (3)0.00048 (19)−0.0079 (2)
O10.0349 (7)0.0362 (7)0.0229 (6)0.0047 (6)0.0003 (6)−0.0048 (5)
O110.0409 (8)0.0482 (8)0.0225 (6)0.0052 (7)−0.0012 (6)0.0014 (6)
N10.0257 (8)0.0610 (12)0.0286 (9)0.0113 (8)−0.0050 (7)−0.0105 (9)
N110.0262 (8)0.0637 (12)0.0241 (8)0.0107 (8)−0.0027 (7)−0.0031 (8)
C10.0187 (8)0.0204 (7)0.0253 (8)−0.0012 (6)0.0007 (7)0.0025 (7)
C20.0214 (8)0.0221 (8)0.0264 (8)0.0025 (7)0.0018 (7)0.0003 (6)
C30.0248 (9)0.0248 (8)0.0238 (8)0.0023 (7)−0.0044 (7)0.0016 (6)
C40.0275 (9)0.0230 (8)0.0235 (8)−0.0024 (7)0.0023 (7)0.0006 (7)
C50.0270 (9)0.0245 (8)0.0308 (9)0.0033 (7)0.0043 (7)−0.0010 (7)
C60.0202 (8)0.0234 (8)0.0313 (9)0.0024 (7)−0.0003 (7)0.0008 (7)
C70.0203 (8)0.0246 (8)0.0272 (9)−0.0018 (7)−0.0013 (7)0.0023 (7)
C80.0461 (12)0.0573 (13)0.0262 (9)0.0095 (12)−0.0060 (10)−0.0073 (9)
C110.0209 (8)0.0222 (8)0.0238 (8)−0.0023 (7)−0.0013 (6)0.0003 (7)
C120.0220 (8)0.0297 (9)0.0299 (9)0.0009 (7)0.0001 (7)−0.0010 (7)
C130.0263 (9)0.0317 (10)0.0296 (9)0.0044 (8)−0.0062 (7)0.0000 (8)
C140.0327 (9)0.0262 (9)0.0234 (8)−0.0037 (8)−0.0022 (7)0.0001 (7)
C150.0277 (9)0.0307 (9)0.0273 (8)0.0045 (8)0.0019 (7)−0.0024 (7)
C160.0252 (9)0.0291 (9)0.0273 (8)0.0051 (8)−0.0015 (7)0.0002 (7)
C170.0232 (8)0.0273 (9)0.0262 (9)−0.0039 (7)−0.0007 (7)−0.0008 (7)
C180.0535 (14)0.0752 (16)0.0263 (9)0.0138 (14)0.0077 (10)−0.0003 (10)
S1—C71.6744 (19)C5—C61.376 (3)
S11—C171.6742 (18)C5—H50.9500
O1—C41.362 (2)C6—H60.9500
O1—C81.431 (2)C8—H8A0.9800
O11—C141.358 (2)C8—H8B0.9800
O11—C181.428 (3)C8—H8C0.9800
N1—C71.316 (2)C11—C161.394 (2)
N1—H1A0.85 (3)C11—C121.401 (2)
N1—H1B0.91 (2)C11—C171.484 (2)
N11—C171.321 (2)C12—C131.381 (2)
N11—H11A0.87 (2)C12—H120.9500
N11—H11B0.88 (3)C13—C141.389 (3)
C1—C21.395 (2)C13—H130.9500
C1—C61.406 (2)C14—C151.391 (2)
C1—C71.481 (2)C15—C161.387 (2)
C2—C31.384 (2)C15—H150.9500
C2—H20.9500C16—H160.9500
C3—C41.390 (2)C18—H18A0.9800
C3—H30.9500C18—H18B0.9800
C4—C51.395 (3)C18—H18C0.9800
C4—O1—C8117.17 (15)H8A—C8—H8B109.5
C14—O11—C18117.87 (16)O1—C8—H8C109.5
C7—N1—H1A124.0 (16)H8A—C8—H8C109.5
C7—N1—H1B119.9 (16)H8B—C8—H8C109.5
H1A—N1—H1B115 (2)C16—C11—C12118.03 (16)
C17—N11—H11A121.8 (16)C16—C11—C17121.70 (16)
C17—N11—H11B121.3 (15)C12—C11—C17120.25 (16)
H11A—N11—H11B116 (2)C13—C12—C11120.82 (17)
C2—C1—C6117.49 (16)C13—C12—H12119.6
C2—C1—C7120.67 (16)C11—C12—H12119.6
C6—C1—C7121.84 (16)C12—C13—C14120.21 (17)
C3—C2—C1121.81 (16)C12—C13—H13119.9
C3—C2—H2119.1C14—C13—H13119.9
C1—C2—H2119.1O11—C14—C13115.64 (16)
C2—C3—C4119.53 (17)O11—C14—C15124.33 (17)
C2—C3—H3120.2C13—C14—C15120.04 (16)
C4—C3—H3120.2C16—C15—C14119.24 (17)
O1—C4—C3124.76 (17)C16—C15—H15120.4
O1—C4—C5115.45 (16)C14—C15—H15120.4
C3—C4—C5119.77 (16)C15—C16—C11121.65 (17)
C6—C5—C4120.07 (17)C15—C16—H16119.2
C6—C5—H5120.0C11—C16—H16119.2
C4—C5—H5120.0N11—C17—C11117.58 (16)
C5—C6—C1121.29 (17)N11—C17—S11120.10 (14)
C5—C6—H6119.4C11—C17—S11122.32 (13)
C1—C6—H6119.4O11—C18—H18A109.5
N1—C7—C1117.58 (17)O11—C18—H18B109.5
N1—C7—S1120.09 (15)H18A—C18—H18B109.5
C1—C7—S1122.33 (13)O11—C18—H18C109.5
O1—C8—H8A109.5H18A—C18—H18C109.5
O1—C8—H8B109.5H18B—C18—H18C109.5
C6—C1—C2—C3−2.0 (3)C16—C11—C12—C13−0.7 (3)
C7—C1—C2—C3178.01 (16)C17—C11—C12—C13177.91 (17)
C1—C2—C3—C40.2 (3)C11—C12—C13—C140.0 (3)
C8—O1—C4—C3−3.6 (3)C18—O11—C14—C13176.58 (19)
C8—O1—C4—C5178.21 (18)C18—O11—C14—C15−3.0 (3)
C2—C3—C4—O1−176.50 (17)C12—C13—C14—O11−178.65 (17)
C2—C3—C4—C51.6 (3)C12—C13—C14—C150.9 (3)
O1—C4—C5—C6176.62 (16)O11—C14—C15—C16178.48 (18)
C3—C4—C5—C6−1.7 (3)C13—C14—C15—C16−1.0 (3)
C4—C5—C6—C1−0.1 (3)C14—C15—C16—C110.3 (3)
C2—C1—C6—C51.9 (3)C12—C11—C16—C150.6 (3)
C7—C1—C6—C5−178.06 (17)C17—C11—C16—C15−178.02 (17)
C2—C1—C7—N1172.04 (18)C16—C11—C17—N1110.3 (3)
C6—C1—C7—N1−8.0 (3)C12—C11—C17—N11−168.26 (18)
C2—C1—C7—S1−7.6 (2)C16—C11—C17—S11−169.92 (14)
C6—C1—C7—S1172.40 (14)C12—C11—C17—S1111.5 (2)
D—H···AD—HH···AD···AD—H···A
N1—H1A···S1i0.85 (3)2.79 (3)3.383 (2)129 (2)
N11—H11B···S11ii0.88 (3)2.63 (2)3.286 (2)132 (2)
C8—H8B···O11iii0.982.543.382 (3)144
N1—H1B···S110.91 (2)2.47 (3)3.368 (2)168 (2)
N11—H11A···S10.87 (2)2.57 (2)3.420 (2)165 (2)
C2—H2···S10.952.693.100 (2)107
C12—H12···S110.952.703.103 (2)106
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1A⋯S1i0.85 (3)2.79 (3)3.383 (2)129 (2)
N11—H11B⋯S11ii0.88 (3)2.63 (2)3.286 (2)132 (2)
C8—H8B⋯O11iii0.982.543.382 (3)144
N1—H1B⋯S110.91 (2)2.47 (3)3.368 (2)168 (2)
N11—H11A⋯S10.87 (2)2.57 (2)3.420 (2)165 (2)
C2—H2⋯S10.952.693.100 (2)107
C12—H12⋯S110.952.703.103 (2)106

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

  5 in total

1.  Thioamides as useful synthons in the synthesis of heterocycles.

Authors:  Tadeusz S Jagodziński
Journal:  Chem Rev       Date:  2003-01       Impact factor: 60.622

2.  A short history of SHELX.

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

3.  3-Methyl-thio-benzamide.

Authors:  Mahmood-Ul-Hassan Khan; Shahid Hameed; Tashfeen Akhtar; Jason D Masuda
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-05-29

4.  4-Chloro-benzothio-amide.

Authors:  Mahmood-Ul-Hassan Khan; Shahid Hameed; Tashfeen Akhtar; Jason D Masuda
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-04-25

5.  4-Bromo-thio-benzamide.

Authors:  Mahmood-Ul-Hassan Khan; Shahid Hameed; Tashfeen Akhtar; Jason D Masuda
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-05-20
  5 in total
  1 in total

1.  4-Methyl-benzene-carbothio-amide.

Authors:  Saqib Ali; Shahid Hameed; Ahmad Luqman; Tashfeen Akhtar; Masood Parvez
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-05-08
  1 in total

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