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The mol­ecule of the title compound, C13H13NOS, is non-planar [the dihedral angle between the least-squares planes defined by the phenyl C atoms and furan ring atoms is 71.7 (2)°]. The anti conformation of the amide and thio groups in the thio­amide fragment is consistent with infinite C(4) chain formation along the b axis via N—H...S intermolecular hydrogen bonds [N...S = 3.444 (3) Å] between the amide group and thio­amide S atom.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804006324/cv6281sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804006324/cv6281Isup2.hkl
Contains datablock I

CCDC reference: 238809

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.048
  • wR factor = 0.114
  • Data-to-parameter ratio = 10.0

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT035_ALERT_1_A No _chemical_absolute_configuration info given . ?
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C13 H13 N O S
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 27.00 From the CIF: _reflns_number_total 1501 Count of symmetry unique reflns 1540 Completeness (_total/calc) 97.47% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2003)'; cell refinement: CrysAlis CCD (Oxford Diffraction, 2003); data reduction: CrysAlis RED (Oxford Diffraction, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON98 (Spek, 1998); software used to prepare material for publication: SHELXL97.

N-benzyl-2-methyl-3-furanthiocarboxanilide top
Crystal data top
C13H13NOSDx = 1.295 Mg m3
Mr = 231.30Melting point = 343–344 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4482 reflections
a = 5.7601 (11) Åθ = 10.0–30.0°
b = 8.9620 (19) ŵ = 0.25 mm1
c = 22.983 (4) ÅT = 296 K
V = 1186.4 (4) Å3Prism, colourless
Z = 40.51 × 0.49 × 0.33 mm
F(000) = 488
Data collection top
Oxford Diffraction Xcalibur2
diffractometer with Sapphire 2 CCD detector
1414 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.074
Graphite monochromatorθmax = 27.0°, θmin = 4.6°
φ and ω scansh = 77
19193 measured reflectionsk = 1111
1501 independent reflectionsl = 2929
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: geom & difmap
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.047P)2 + 0.5024P]
where P = (Fo2 + 2Fc2)/3
1501 reflections(Δ/σ)max < 0.001
150 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.19 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.83967 (16)0.07172 (10)0.22959 (4)0.0548 (3)
N0.6001 (5)0.3180 (3)0.24766 (11)0.0451 (6)
H1N0.514 (8)0.391 (5)0.2374 (18)0.073 (13)*
O0.4742 (7)0.1972 (4)0.05845 (11)0.0800 (10)
C10.5493 (7)0.2211 (4)0.15327 (13)0.0468 (7)
C20.3480 (8)0.3082 (4)0.13867 (15)0.0628 (9)
H20.26120.36650.16410.075*
C30.3087 (10)0.2899 (5)0.08203 (18)0.0793 (13)
H30.18730.33340.06140.095*
C40.6190 (8)0.1547 (4)0.10248 (14)0.0607 (10)
C50.6583 (6)0.2099 (3)0.21093 (12)0.0406 (6)
C60.6806 (6)0.3283 (3)0.30758 (12)0.0444 (7)
H6A0.83980.29320.30920.053*
H6B0.68070.43240.31900.053*
C70.5378 (5)0.2405 (3)0.35143 (12)0.0400 (6)
C80.6107 (6)0.2386 (4)0.40892 (14)0.0534 (8)
H80.74720.28750.41910.064*
C90.4844 (8)0.1656 (5)0.45123 (15)0.0647 (11)
H90.53460.16620.48970.078*
C100.2828 (7)0.0915 (5)0.43613 (17)0.0648 (10)
H100.19740.04140.46440.078*
C110.2081 (6)0.0920 (4)0.37883 (16)0.0597 (9)
H110.07250.04220.36870.072*
C120.3350 (6)0.1665 (4)0.33668 (13)0.0463 (7)
H120.28380.16680.29830.056*
C130.8109 (10)0.0544 (5)0.08501 (17)0.0829 (14)
H13A0.84970.07220.04500.124*
H13B0.94420.07360.10900.124*
H13C0.76320.04750.08980.124*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0527 (4)0.0545 (5)0.0571 (5)0.0075 (4)0.0011 (4)0.0056 (4)
N0.0551 (15)0.0420 (13)0.0382 (12)0.0044 (12)0.0038 (11)0.0024 (11)
O0.118 (3)0.086 (2)0.0354 (12)0.033 (2)0.0074 (15)0.0015 (13)
C10.0590 (19)0.0461 (16)0.0353 (14)0.0117 (15)0.0015 (14)0.0036 (13)
C20.070 (2)0.068 (2)0.0510 (18)0.004 (2)0.0069 (19)0.0082 (16)
C30.092 (3)0.094 (3)0.051 (2)0.013 (3)0.021 (2)0.017 (2)
C40.086 (3)0.057 (2)0.0396 (15)0.025 (2)0.0067 (17)0.0017 (14)
C50.0462 (15)0.0401 (14)0.0353 (12)0.0111 (14)0.0066 (13)0.0005 (11)
C60.0462 (15)0.0441 (15)0.0428 (14)0.0008 (15)0.0048 (13)0.0063 (12)
C70.0407 (15)0.0456 (16)0.0337 (13)0.0075 (14)0.0027 (12)0.0051 (12)
C80.0523 (19)0.066 (2)0.0415 (15)0.0025 (17)0.0090 (14)0.0040 (15)
C90.073 (3)0.082 (3)0.0388 (16)0.010 (2)0.0014 (17)0.0028 (18)
C100.069 (2)0.069 (2)0.056 (2)0.002 (2)0.0184 (18)0.0049 (19)
C110.0481 (18)0.071 (2)0.0605 (19)0.0076 (19)0.0047 (16)0.0053 (18)
C120.0402 (15)0.0568 (17)0.0420 (14)0.0003 (16)0.0049 (14)0.0047 (13)
C130.108 (4)0.082 (3)0.059 (2)0.014 (3)0.032 (3)0.021 (2)
Geometric parameters (Å, º) top
S1—C51.676 (3)C6—H6B0.9700
N—C51.327 (4)C7—C121.386 (4)
N—C61.456 (4)C7—C81.386 (4)
N—H1N0.85 (5)C8—C91.379 (5)
O—C41.366 (5)C8—H80.9300
O—C31.376 (6)C9—C101.382 (6)
C1—C41.370 (5)C9—H90.9300
C1—C21.438 (5)C10—C111.385 (5)
C1—C51.470 (4)C10—H100.9300
C2—C31.331 (5)C11—C121.385 (5)
C2—H20.9300C11—H110.9300
C3—H30.9300C12—H120.9300
C4—C131.480 (6)C13—H13A0.9600
C6—C71.520 (4)C13—H13B0.9600
C6—H6A0.9700C13—H13C0.9600
C5—N—C6124.6 (3)C12—C7—C8118.8 (3)
C5—N—H1N122 (3)C12—C7—C6122.8 (3)
C6—N—H1N114 (3)C8—C7—C6118.3 (3)
C4—O—C3107.4 (3)C9—C8—C7121.2 (3)
C4—C1—C2105.9 (3)C9—C8—H8119.4
C4—C1—C5127.8 (3)C7—C8—H8119.4
C2—C1—C5126.3 (3)C8—C9—C10119.6 (3)
C3—C2—C1107.3 (4)C8—C9—H9120.2
C3—C2—H2126.3C10—C9—H9120.2
C1—C2—H2126.3C9—C10—C11119.9 (4)
C2—C3—O110.0 (4)C9—C10—H10120.1
C2—C3—H3125.0C11—C10—H10120.1
O—C3—H3125.0C12—C11—C10120.2 (3)
O—C4—C1109.4 (4)C12—C11—H11119.9
O—C4—C13115.1 (3)C10—C11—H11119.9
C1—C4—C13135.5 (4)C11—C12—C7120.3 (3)
N—C5—C1114.6 (3)C11—C12—H12119.9
N—C5—S1122.2 (2)C7—C12—H12119.9
C1—C5—S1123.2 (2)C4—C13—H13A109.5
N—C6—C7114.9 (3)C4—C13—H13B109.5
N—C6—H6A108.5H13A—C13—H13B109.5
C7—C6—H6A108.5C4—C13—H13C109.5
N—C6—H6B108.5H13A—C13—H13C109.5
C7—C6—H6B108.5H13B—C13—H13C109.5
H6A—C6—H6B107.5
C4—C1—C2—C30.1 (4)C4—C1—C5—S120.0 (5)
C5—C1—C2—C3178.9 (4)C2—C1—C5—S1161.5 (3)
C1—C2—C3—O0.7 (5)C5—N—C6—C785.5 (4)
C4—O—C3—C21.0 (5)N—C6—C7—C125.2 (4)
C3—O—C4—C10.9 (4)N—C6—C7—C8176.7 (3)
C3—O—C4—C13179.6 (3)C12—C7—C8—C90.4 (5)
C2—C1—C4—O0.5 (4)C6—C7—C8—C9177.7 (3)
C5—C1—C4—O178.2 (3)C7—C8—C9—C100.7 (6)
C2—C1—C4—C13178.8 (4)C8—C9—C10—C110.5 (6)
C5—C1—C4—C130.1 (7)C9—C10—C11—C120.0 (6)
C6—N—C5—C1178.2 (3)C10—C11—C12—C70.2 (5)
C6—N—C5—S11.2 (4)C8—C7—C12—C110.0 (5)
C4—C1—C5—N160.5 (3)C6—C7—C12—C11178.0 (3)
C2—C1—C5—N17.9 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H1N···S1i0.85 (5)2.71 (5)3.444 (3)145 (4)
Symmetry code: (i) x+1, y+1/2, z1/2.
 

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