Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801013472/wn6043sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801013472/wn6043Isup2.hkl |
CCDC reference: 172225
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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.
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.
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.
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. |
C13H13NOS | Dx = 1.240 Mg m−3 |
Mr = 231.30 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 33 reflections |
a = 9.577 (3) Å | θ = 11.9–16.4° |
b = 16.039 (3) Å | µ = 0.24 mm−1 |
c = 16.127 (2) Å | T = 293 K |
V = 2477.2 (10) Å3 | Prism, yellow |
Z = 8 | 0.34 × 0.26 × 0.11 mm |
F(000) = 976 |
Philips PW1100 updated by Stoe diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 27.0°, θmin = 2.5° |
Planar graphite monochromator | h = 0→12 |
θ/2θ scans | k = 0→20 |
2671 measured reflections | l = 0→20 |
2671 independent reflections | 4 standard reflections every 90 min |
1280 reflections with I > 2σ(I) | intensity decay: 2.4% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.053 | H 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 reflections | Δρmax = 0.35 e Å−3 |
174 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.015 (2) |
C13H13NOS | V = 2477.2 (10) Å3 |
Mr = 231.30 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 9.577 (3) Å | µ = 0.24 mm−1 |
b = 16.039 (3) Å | T = 293 K |
c = 16.127 (2) Å | 0.34 × 0.26 × 0.11 mm |
Philips PW1100 updated by Stoe diffractometer | Rint = 0.000 |
2671 measured reflections | 4 standard reflections every 90 min |
2671 independent reflections | intensity decay: 2.4% |
1280 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.167 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | Δρmax = 0.35 e Å−3 |
2671 reflections | Δρmin = −0.17 e Å−3 |
174 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.1588 (5) | 0.2353 (2) | 0.6408 (2) | 0.0767 (10) | |
C2 | 0.0677 (5) | 0.2584 (3) | 0.6967 (3) | 0.0924 (12) | |
O1 | −0.0628 (2) | 0.22716 (15) | 0.67979 (14) | 0.0785 (7) | |
C3 | −0.0517 (4) | 0.1839 (2) | 0.6076 (2) | 0.0762 (9) | |
C4 | −0.1787 (4) | 0.1443 (3) | 0.5778 (3) | 0.1054 (14) | |
H41 | −0.2551 | 0.1587 | 0.6137 | 0.158* | |
H42 | −0.1666 | 0.0849 | 0.5775 | 0.158* | |
H43 | −0.1985 | 0.1633 | 0.5226 | 0.158* | |
C5 | 0.0803 (3) | 0.18494 (19) | 0.58081 (18) | 0.0605 (8) | |
C6 | 0.1366 (3) | 0.14937 (16) | 0.50283 (15) | 0.0529 (7) | |
S1 | 0.05308 (9) | 0.16177 (6) | 0.41301 (5) | 0.0778 (4) | |
N1 | 0.2614 (2) | 0.11279 (14) | 0.50910 (12) | 0.0545 (6) | |
C7 | 0.3426 (4) | 0.0903 (2) | 0.43517 (18) | 0.0846 (11) | |
H71 | 0.4288 | 0.0648 | 0.4518 | 0.127* | |
H72 | 0.3620 | 0.1396 | 0.4034 | 0.127* | |
H73 | 0.2900 | 0.0519 | 0.4019 | 0.127* | |
C8 | 0.3100 (3) | 0.07707 (16) | 0.58597 (15) | 0.0503 (6) | |
C9 | 0.4345 (3) | 0.1038 (2) | 0.6219 (2) | 0.0647 (8) | |
C10 | 0.4806 (4) | 0.0663 (2) | 0.6938 (2) | 0.0722 (9) | |
C11 | 0.4074 (4) | 0.0035 (2) | 0.7287 (2) | 0.0755 (10) | |
C12 | 0.2849 (4) | −0.0237 (2) | 0.6942 (2) | 0.0708 (9) | |
C13 | 0.2370 (3) | 0.01352 (18) | 0.62140 (18) | 0.0582 (7) | |
H1 | 0.248 (4) | 0.253 (3) | 0.642 (2) | 0.108 (14)* | |
H2 | 0.086 (4) | 0.294 (2) | 0.752 (3) | 0.111 (12)* | |
H9 | 0.472 (3) | 0.1471 (17) | 0.5983 (16) | 0.049 (8)* | |
H10 | 0.561 (3) | 0.087 (2) | 0.717 (2) | 0.081 (11)* | |
H11 | 0.443 (3) | −0.015 (2) | 0.780 (2) | 0.093 (11)* | |
H12 | 0.229 (3) | −0.0723 (19) | 0.7174 (17) | 0.069 (8)* | |
H13 | 0.154 (3) | −0.0021 (16) | 0.5985 (15) | 0.057 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.089 (3) | 0.075 (2) | 0.067 (2) | 0.011 (2) | 0.006 (2) | −0.0139 (17) |
C2 | 0.123 (3) | 0.083 (2) | 0.071 (2) | 0.013 (2) | −0.004 (2) | −0.014 (2) |
O1 | 0.0851 (17) | 0.0807 (16) | 0.0697 (14) | 0.0220 (13) | 0.0199 (12) | −0.0006 (12) |
C3 | 0.077 (2) | 0.075 (2) | 0.076 (2) | 0.0172 (18) | 0.0041 (17) | 0.0131 (17) |
C4 | 0.074 (3) | 0.111 (3) | 0.131 (4) | −0.005 (2) | 0.001 (2) | 0.018 (3) |
C5 | 0.0632 (19) | 0.0608 (17) | 0.0576 (17) | 0.0095 (15) | 0.0010 (14) | 0.0059 (14) |
C6 | 0.0606 (18) | 0.0457 (15) | 0.0523 (16) | −0.0044 (13) | 0.0024 (13) | 0.0022 (12) |
S1 | 0.0928 (7) | 0.0837 (6) | 0.0567 (5) | 0.0011 (5) | −0.0162 (4) | 0.0045 (4) |
N1 | 0.0607 (14) | 0.0569 (13) | 0.0459 (12) | 0.0039 (12) | 0.0059 (11) | 0.0014 (10) |
C7 | 0.095 (3) | 0.094 (2) | 0.0645 (19) | 0.015 (2) | 0.0309 (18) | 0.0064 (18) |
C8 | 0.0537 (16) | 0.0466 (14) | 0.0506 (14) | 0.0058 (12) | 0.0064 (12) | −0.0030 (12) |
C9 | 0.0557 (19) | 0.0580 (18) | 0.080 (2) | −0.0021 (16) | 0.0011 (17) | 0.0026 (16) |
C10 | 0.066 (2) | 0.074 (2) | 0.077 (2) | 0.0130 (19) | −0.0141 (18) | −0.0068 (19) |
C11 | 0.080 (2) | 0.084 (2) | 0.063 (2) | 0.026 (2) | 0.0002 (18) | 0.0061 (18) |
C12 | 0.074 (2) | 0.066 (2) | 0.072 (2) | 0.0093 (17) | 0.0159 (18) | 0.0149 (17) |
C13 | 0.0565 (18) | 0.0562 (17) | 0.0618 (17) | 0.0006 (15) | 0.0036 (15) | −0.0003 (15) |
C1—C2 | 1.308 (5) | N1—C7 | 1.468 (3) |
C1—C5 | 1.467 (5) | C7—H71 | 0.9600 |
C1—H1 | 0.90 (4) | C7—H72 | 0.9600 |
C2—O1 | 1.374 (5) | C7—H73 | 0.9600 |
C2—H2 | 1.08 (4) | C8—C13 | 1.362 (4) |
O1—C3 | 1.360 (4) | C8—C9 | 1.393 (4) |
C3—C5 | 1.336 (4) | C9—C10 | 1.379 (5) |
C3—C4 | 1.454 (5) | C9—H9 | 0.87 (3) |
C4—H41 | 0.9600 | C10—C11 | 1.350 (5) |
C4—H42 | 0.9600 | C10—H10 | 0.92 (3) |
C4—H43 | 0.9600 | C11—C12 | 1.370 (5) |
C5—C6 | 1.483 (4) | C11—H11 | 0.95 (4) |
C6—N1 | 1.335 (3) | C12—C13 | 1.395 (4) |
C6—S1 | 1.667 (3) | C12—H12 | 1.02 (3) |
N1—C8 | 1.443 (3) | C13—H13 | 0.91 (3) |
C2—C1—C5 | 105.6 (4) | N1—C7—H71 | 109.5 |
C2—C1—H1 | 122 (3) | N1—C7—H72 | 109.5 |
C5—C1—H1 | 132 (2) | H71—C7—H72 | 109.5 |
C1—C2—O1 | 111.5 (4) | N1—C7—H73 | 109.5 |
C1—C2—H2 | 128 (2) | H71—C7—H73 | 109.5 |
O1—C2—H2 | 120 (2) | H72—C7—H73 | 109.5 |
C3—O1—C2 | 106.6 (3) | C13—C8—C9 | 119.7 (3) |
C5—C3—O1 | 110.1 (3) | C13—C8—N1 | 119.5 (3) |
C5—C3—C4 | 133.7 (4) | C9—C8—N1 | 120.8 (3) |
O1—C3—C4 | 116.1 (3) | C10—C9—C8 | 119.3 (3) |
C3—C4—H41 | 109.5 | C10—C9—H9 | 125.7 (18) |
C3—C4—H42 | 109.5 | C8—C9—H9 | 114.8 (18) |
H41—C4—H42 | 109.5 | C11—C10—C9 | 120.7 (4) |
C3—C4—H43 | 109.5 | C11—C10—H10 | 123 (2) |
H41—C4—H43 | 109.5 | C9—C10—H10 | 116 (2) |
H42—C4—H43 | 109.5 | C10—C11—C12 | 120.8 (3) |
C3—C5—C1 | 106.2 (3) | C10—C11—H11 | 114 (2) |
C3—C5—C6 | 127.9 (3) | C12—C11—H11 | 125 (2) |
C1—C5—C6 | 125.7 (3) | C11—C12—C13 | 119.2 (3) |
N1—C6—C5 | 115.5 (2) | C11—C12—H12 | 123.0 (16) |
N1—C6—S1 | 123.2 (2) | C13—C12—H12 | 117.7 (16) |
C5—C6—S1 | 121.1 (2) | C8—C13—C12 | 120.3 (3) |
C6—N1—C8 | 121.9 (2) | C8—C13—H13 | 118.9 (17) |
C6—N1—C7 | 121.3 (2) | C12—C13—H13 | 120.7 (17) |
C8—N1—C7 | 115.4 (2) |
Experimental details
Crystal data | |
Chemical formula | C13H13NOS |
Mr | 231.30 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 293 |
a, b, c (Å) | 9.577 (3), 16.039 (3), 16.127 (2) |
V (Å3) | 2477.2 (10) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.34 × 0.26 × 0.11 |
Data collection | |
Diffractometer | Philips PW1100 updated by Stoe diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2671, 2671, 1280 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.167, 0.97 |
No. of reflections | 2671 |
No. of parameters | 174 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 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.
C5—C6 | 1.483 (4) | N1—C8 | 1.443 (3) |
C6—N1 | 1.335 (3) | N1—C7 | 1.468 (3) |
C6—S1 | 1.667 (3) | ||
N1—C6—C5 | 115.5 (2) | C6—N1—C8 | 121.9 (2) |
N1—C6—S1 | 123.2 (2) | C6—N1—C7 | 121.3 (2) |
C5—C6—S1 | 121.1 (2) | C8—N1—C7 | 115.4 (2) |
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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 Csp2═Csp2 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 C═S bond length is consistent with the average value found in the fragment X2C═S (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)°.