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The title compound, C13H13NOS, was prepared and structurally characterized. The mol­ecule is not planar; the furan ring is inclined at an angle of 26.5° to the phenyl ring. The crystal structure is dominated by van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801013472/wn6043sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801013472/wn6043Isup2.hkl
Contains datablock I

CCDC reference: 172225

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.053
  • wR factor = 0.167
  • Data-to-parameter ratio = 15.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Comment top

The biological activity of N-arylfuranthiocarboxamides has been well known for years (Landquist, 1984). N-Aryl-3-furanthiocarboxamides were less investigated due to difficulties in their synthesis and unrecognized pharmaceutical importance (Dodd et al., 1970). Fungicidal and insecticidal activity of the derivatives of 3-furancarboxylic acid has encouraged the synthesis of new N-aryl-3-furanthiocarboxamide derivatives.

In order to get more information on the structural criteria that an organic molecule must fulfill to exhibit such activity, we investigated the structure of the title compound, (I).

Its antibacterial activity is currently under preliminary investigation. A survey of the Cambridge Structural Database (Allen & Kennard, 1993) revealed only two structures involving furanthioamide, viz. N-(2-hydroxyethyl)-2-thiofuramide (FELYIE; Galešić et al., 1987) and 5-nitro-N-phenyl-2-thiofuramide (KOPGUR; Pavlović et al., 2000). The Csp2Csp2 and Csp2—O bond distances within the furan ring are in agreement with literature data (Allen et al., 1987). The Csp2—Csp2 bond distance value is slightly longer than the average value of 1.432 Å (Allen et al., 1987). The CS bond length is consistent with the average value found in the fragment X2CS (X = C, N, O, S) of 1.671 Å, as well as in N-(2-hydroxyethyl)-2-thiofuramide (Galešić et al., 1987). The C—N distances of the thioamide moiety correspond to single C—N bond values, while N1—C6 is quite shorter as a result of π-electron delocalization. In the structure of N-(2-hydroxyethyl)-2-thiofuramide (Galešić et al., 1987), the analogous bond length is even shorter, 1.317 (4) Å. The sum of the angle values around the thioamido N atom is 358.7 (2)°, confirming sp2-hybridization. The title molecule is not planar, exibiting twisting around the single Nsp2 bond (N1—C6). The measure of twisting is described by the torsion angle C3—C5—C6—N1 of -140.9 (2)°.

Experimental top

The title compound was prepared by thionylation of the corresponding amide with phosphourus pentasulfide, according to the reported procedure (Hahn et al., 1970). By recrystallization from ethanol prismatic crystals of good diffraction quality were obtained.

Refinement top

The H atoms attached to the C atoms of the furan and phenyl ring were generated geometrically and refined using the riding model. Those belonging to the methyl groups were located in the difference Fourier map.

Computing details top

Data collection: STADI4 (Stoe & Cie, 1995); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1998); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. PLATON drawing (Spek, 1998) with the atom-numbering scheme. The displacement ellipsoids are at the 50% probability level for the non-H atoms. H atoms are shown as spheres of arbitrary radii.
N-methyl-2-methyl-3-furanthiocarboxanilyd top
Crystal data top
C13H13NOSDx = 1.240 Mg m3
Mr = 231.30Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 33 reflections
a = 9.577 (3) Åθ = 11.9–16.4°
b = 16.039 (3) ŵ = 0.24 mm1
c = 16.127 (2) ÅT = 293 K
V = 2477.2 (10) Å3Prism, yellow
Z = 80.34 × 0.26 × 0.11 mm
F(000) = 976
Data collection top
Philips PW1100 updated by Stoe
diffractometer
Rint = 0.000
Radiation source: fine-focus sealed tubeθmax = 27.0°, θmin = 2.5°
Planar graphite monochromatorh = 012
θ/2θ scansk = 020
2671 measured reflectionsl = 020
2671 independent reflections4 standard reflections every 90 min
1280 reflections with I > 2σ(I) intensity decay: 2.4%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.167 w = 1/[σ2(Fo2) + (0.0849P)2 + 0.4315P]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max < 0.001
2671 reflectionsΔρmax = 0.35 e Å3
174 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.015 (2)
Crystal data top
C13H13NOSV = 2477.2 (10) Å3
Mr = 231.30Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 9.577 (3) ŵ = 0.24 mm1
b = 16.039 (3) ÅT = 293 K
c = 16.127 (2) Å0.34 × 0.26 × 0.11 mm
Data collection top
Philips PW1100 updated by Stoe
diffractometer
Rint = 0.000
2671 measured reflections4 standard reflections every 90 min
2671 independent reflections intensity decay: 2.4%
1280 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.167H atoms treated by a mixture of independent and constrained refinement
S = 0.97Δρmax = 0.35 e Å3
2671 reflectionsΔρmin = 0.17 e Å3
174 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.1588 (5)0.2353 (2)0.6408 (2)0.0767 (10)
C20.0677 (5)0.2584 (3)0.6967 (3)0.0924 (12)
O10.0628 (2)0.22716 (15)0.67979 (14)0.0785 (7)
C30.0517 (4)0.1839 (2)0.6076 (2)0.0762 (9)
C40.1787 (4)0.1443 (3)0.5778 (3)0.1054 (14)
H410.25510.15870.61370.158*
H420.16660.08490.57750.158*
H430.19850.16330.52260.158*
C50.0803 (3)0.18494 (19)0.58081 (18)0.0605 (8)
C60.1366 (3)0.14937 (16)0.50283 (15)0.0529 (7)
S10.05308 (9)0.16177 (6)0.41301 (5)0.0778 (4)
N10.2614 (2)0.11279 (14)0.50910 (12)0.0545 (6)
C70.3426 (4)0.0903 (2)0.43517 (18)0.0846 (11)
H710.42880.06480.45180.127*
H720.36200.13960.40340.127*
H730.29000.05190.40190.127*
C80.3100 (3)0.07707 (16)0.58597 (15)0.0503 (6)
C90.4345 (3)0.1038 (2)0.6219 (2)0.0647 (8)
C100.4806 (4)0.0663 (2)0.6938 (2)0.0722 (9)
C110.4074 (4)0.0035 (2)0.7287 (2)0.0755 (10)
C120.2849 (4)0.0237 (2)0.6942 (2)0.0708 (9)
C130.2370 (3)0.01352 (18)0.62140 (18)0.0582 (7)
H10.248 (4)0.253 (3)0.642 (2)0.108 (14)*
H20.086 (4)0.294 (2)0.752 (3)0.111 (12)*
H90.472 (3)0.1471 (17)0.5983 (16)0.049 (8)*
H100.561 (3)0.087 (2)0.717 (2)0.081 (11)*
H110.443 (3)0.015 (2)0.780 (2)0.093 (11)*
H120.229 (3)0.0723 (19)0.7174 (17)0.069 (8)*
H130.154 (3)0.0021 (16)0.5985 (15)0.057 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.089 (3)0.075 (2)0.067 (2)0.011 (2)0.006 (2)0.0139 (17)
C20.123 (3)0.083 (2)0.071 (2)0.013 (2)0.004 (2)0.014 (2)
O10.0851 (17)0.0807 (16)0.0697 (14)0.0220 (13)0.0199 (12)0.0006 (12)
C30.077 (2)0.075 (2)0.076 (2)0.0172 (18)0.0041 (17)0.0131 (17)
C40.074 (3)0.111 (3)0.131 (4)0.005 (2)0.001 (2)0.018 (3)
C50.0632 (19)0.0608 (17)0.0576 (17)0.0095 (15)0.0010 (14)0.0059 (14)
C60.0606 (18)0.0457 (15)0.0523 (16)0.0044 (13)0.0024 (13)0.0022 (12)
S10.0928 (7)0.0837 (6)0.0567 (5)0.0011 (5)0.0162 (4)0.0045 (4)
N10.0607 (14)0.0569 (13)0.0459 (12)0.0039 (12)0.0059 (11)0.0014 (10)
C70.095 (3)0.094 (2)0.0645 (19)0.015 (2)0.0309 (18)0.0064 (18)
C80.0537 (16)0.0466 (14)0.0506 (14)0.0058 (12)0.0064 (12)0.0030 (12)
C90.0557 (19)0.0580 (18)0.080 (2)0.0021 (16)0.0011 (17)0.0026 (16)
C100.066 (2)0.074 (2)0.077 (2)0.0130 (19)0.0141 (18)0.0068 (19)
C110.080 (2)0.084 (2)0.063 (2)0.026 (2)0.0002 (18)0.0061 (18)
C120.074 (2)0.066 (2)0.072 (2)0.0093 (17)0.0159 (18)0.0149 (17)
C130.0565 (18)0.0562 (17)0.0618 (17)0.0006 (15)0.0036 (15)0.0003 (15)
Geometric parameters (Å, º) top
C1—C21.308 (5)N1—C71.468 (3)
C1—C51.467 (5)C7—H710.9600
C1—H10.90 (4)C7—H720.9600
C2—O11.374 (5)C7—H730.9600
C2—H21.08 (4)C8—C131.362 (4)
O1—C31.360 (4)C8—C91.393 (4)
C3—C51.336 (4)C9—C101.379 (5)
C3—C41.454 (5)C9—H90.87 (3)
C4—H410.9600C10—C111.350 (5)
C4—H420.9600C10—H100.92 (3)
C4—H430.9600C11—C121.370 (5)
C5—C61.483 (4)C11—H110.95 (4)
C6—N11.335 (3)C12—C131.395 (4)
C6—S11.667 (3)C12—H121.02 (3)
N1—C81.443 (3)C13—H130.91 (3)
C2—C1—C5105.6 (4)N1—C7—H71109.5
C2—C1—H1122 (3)N1—C7—H72109.5
C5—C1—H1132 (2)H71—C7—H72109.5
C1—C2—O1111.5 (4)N1—C7—H73109.5
C1—C2—H2128 (2)H71—C7—H73109.5
O1—C2—H2120 (2)H72—C7—H73109.5
C3—O1—C2106.6 (3)C13—C8—C9119.7 (3)
C5—C3—O1110.1 (3)C13—C8—N1119.5 (3)
C5—C3—C4133.7 (4)C9—C8—N1120.8 (3)
O1—C3—C4116.1 (3)C10—C9—C8119.3 (3)
C3—C4—H41109.5C10—C9—H9125.7 (18)
C3—C4—H42109.5C8—C9—H9114.8 (18)
H41—C4—H42109.5C11—C10—C9120.7 (4)
C3—C4—H43109.5C11—C10—H10123 (2)
H41—C4—H43109.5C9—C10—H10116 (2)
H42—C4—H43109.5C10—C11—C12120.8 (3)
C3—C5—C1106.2 (3)C10—C11—H11114 (2)
C3—C5—C6127.9 (3)C12—C11—H11125 (2)
C1—C5—C6125.7 (3)C11—C12—C13119.2 (3)
N1—C6—C5115.5 (2)C11—C12—H12123.0 (16)
N1—C6—S1123.2 (2)C13—C12—H12117.7 (16)
C5—C6—S1121.1 (2)C8—C13—C12120.3 (3)
C6—N1—C8121.9 (2)C8—C13—H13118.9 (17)
C6—N1—C7121.3 (2)C12—C13—H13120.7 (17)
C8—N1—C7115.4 (2)

Experimental details

Crystal data
Chemical formulaC13H13NOS
Mr231.30
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)293
a, b, c (Å)9.577 (3), 16.039 (3), 16.127 (2)
V3)2477.2 (10)
Z8
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.34 × 0.26 × 0.11
Data collection
DiffractometerPhilips PW1100 updated by Stoe
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
2671, 2671, 1280
Rint0.000
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.167, 0.97
No. of reflections2671
No. of parameters174
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.35, 0.17

Computer programs: STADI4 (Stoe & Cie, 1995), STADI4, X-RED (Stoe & Cie, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1998), SHELXL97.

Selected geometric parameters (Å, º) top
C5—C61.483 (4)N1—C81.443 (3)
C6—N11.335 (3)N1—C71.468 (3)
C6—S11.667 (3)
N1—C6—C5115.5 (2)C6—N1—C8121.9 (2)
N1—C6—S1123.2 (2)C6—N1—C7121.3 (2)
C5—C6—S1121.1 (2)C8—N1—C7115.4 (2)
 

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