Buy article online - an online subscription or single-article purchase is required to access this article.
The molecule of the title compound, C
13H
13NOS, 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
CCDC reference: 238809
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (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
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
C13H13NOS | Dx = 1.295 Mg m−3 |
Mr = 231.30 | Melting point = 343–344 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4482 reflections |
a = 5.7601 (11) Å | θ = 10.0–30.0° |
b = 8.9620 (19) Å | µ = 0.25 mm−1 |
c = 22.983 (4) Å | T = 296 K |
V = 1186.4 (4) Å3 | Prism, colourless |
Z = 4 | 0.51 × 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 tube | Rint = 0.074 |
Graphite monochromator | θmax = 27.0°, θmin = 4.6° |
φ and ω scans | h = −7→7 |
19193 measured reflections | k = −11→11 |
1501 independent reflections | l = −29→29 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: geom & difmap |
wR(F2) = 0.114 | H 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 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.83967 (16) | 0.07172 (10) | −0.22959 (4) | 0.0548 (3) | |
N | 0.6001 (5) | 0.3180 (3) | −0.24766 (11) | 0.0451 (6) | |
H1N | 0.514 (8) | 0.391 (5) | −0.2374 (18) | 0.073 (13)* | |
O | 0.4742 (7) | 0.1972 (4) | −0.05845 (11) | 0.0800 (10) | |
C1 | 0.5493 (7) | 0.2211 (4) | −0.15327 (13) | 0.0468 (7) | |
C2 | 0.3480 (8) | 0.3082 (4) | −0.13867 (15) | 0.0628 (9) | |
H2 | 0.2612 | 0.3665 | −0.1641 | 0.075* | |
C3 | 0.3087 (10) | 0.2899 (5) | −0.08203 (18) | 0.0793 (13) | |
H3 | 0.1873 | 0.3334 | −0.0614 | 0.095* | |
C4 | 0.6190 (8) | 0.1547 (4) | −0.10248 (14) | 0.0607 (10) | |
C5 | 0.6583 (6) | 0.2099 (3) | −0.21093 (12) | 0.0406 (6) | |
C6 | 0.6806 (6) | 0.3283 (3) | −0.30758 (12) | 0.0444 (7) | |
H6A | 0.8398 | 0.2932 | −0.3092 | 0.053* | |
H6B | 0.6807 | 0.4324 | −0.3190 | 0.053* | |
C7 | 0.5378 (5) | 0.2405 (3) | −0.35143 (12) | 0.0400 (6) | |
C8 | 0.6107 (6) | 0.2386 (4) | −0.40892 (14) | 0.0534 (8) | |
H8 | 0.7472 | 0.2875 | −0.4191 | 0.064* | |
C9 | 0.4844 (8) | 0.1656 (5) | −0.45123 (15) | 0.0647 (11) | |
H9 | 0.5346 | 0.1662 | −0.4897 | 0.078* | |
C10 | 0.2828 (7) | 0.0915 (5) | −0.43613 (17) | 0.0648 (10) | |
H10 | 0.1974 | 0.0414 | −0.4644 | 0.078* | |
C11 | 0.2081 (6) | 0.0920 (4) | −0.37883 (16) | 0.0597 (9) | |
H11 | 0.0725 | 0.0422 | −0.3687 | 0.072* | |
C12 | 0.3350 (6) | 0.1665 (4) | −0.33668 (13) | 0.0463 (7) | |
H12 | 0.2838 | 0.1668 | −0.2983 | 0.056* | |
C13 | 0.8109 (10) | 0.0544 (5) | −0.08501 (17) | 0.0829 (14) | |
H13A | 0.8497 | 0.0722 | −0.0450 | 0.124* | |
H13B | 0.9442 | 0.0736 | −0.1090 | 0.124* | |
H13C | 0.7632 | −0.0475 | −0.0898 | 0.124* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0527 (4) | 0.0545 (5) | 0.0571 (5) | 0.0075 (4) | −0.0011 (4) | 0.0056 (4) |
N | 0.0551 (15) | 0.0420 (13) | 0.0382 (12) | 0.0044 (12) | 0.0038 (11) | 0.0024 (11) |
O | 0.118 (3) | 0.086 (2) | 0.0354 (12) | −0.033 (2) | 0.0074 (15) | −0.0015 (13) |
C1 | 0.0590 (19) | 0.0461 (16) | 0.0353 (14) | −0.0117 (15) | 0.0015 (14) | −0.0036 (13) |
C2 | 0.070 (2) | 0.068 (2) | 0.0510 (18) | −0.004 (2) | 0.0069 (19) | −0.0082 (16) |
C3 | 0.092 (3) | 0.094 (3) | 0.051 (2) | −0.013 (3) | 0.021 (2) | −0.017 (2) |
C4 | 0.086 (3) | 0.057 (2) | 0.0396 (15) | −0.025 (2) | −0.0067 (17) | 0.0017 (14) |
C5 | 0.0462 (15) | 0.0401 (14) | 0.0353 (12) | −0.0111 (14) | −0.0066 (13) | −0.0005 (11) |
C6 | 0.0462 (15) | 0.0441 (15) | 0.0428 (14) | 0.0008 (15) | 0.0048 (13) | 0.0063 (12) |
C7 | 0.0407 (15) | 0.0456 (16) | 0.0337 (13) | 0.0075 (14) | 0.0027 (12) | 0.0051 (12) |
C8 | 0.0523 (19) | 0.066 (2) | 0.0415 (15) | 0.0025 (17) | 0.0090 (14) | 0.0040 (15) |
C9 | 0.073 (3) | 0.082 (3) | 0.0388 (16) | 0.010 (2) | 0.0014 (17) | −0.0028 (18) |
C10 | 0.069 (2) | 0.069 (2) | 0.056 (2) | 0.002 (2) | −0.0184 (18) | −0.0049 (19) |
C11 | 0.0481 (18) | 0.071 (2) | 0.0605 (19) | −0.0076 (19) | −0.0047 (16) | 0.0053 (18) |
C12 | 0.0402 (15) | 0.0568 (17) | 0.0420 (14) | −0.0003 (16) | 0.0049 (14) | 0.0047 (13) |
C13 | 0.108 (4) | 0.082 (3) | 0.059 (2) | −0.014 (3) | −0.032 (3) | 0.021 (2) |
Geometric parameters (Å, º) top
S1—C5 | 1.676 (3) | C6—H6B | 0.9700 |
N—C5 | 1.327 (4) | C7—C12 | 1.386 (4) |
N—C6 | 1.456 (4) | C7—C8 | 1.386 (4) |
N—H1N | 0.85 (5) | C8—C9 | 1.379 (5) |
O—C4 | 1.366 (5) | C8—H8 | 0.9300 |
O—C3 | 1.376 (6) | C9—C10 | 1.382 (6) |
C1—C4 | 1.370 (5) | C9—H9 | 0.9300 |
C1—C2 | 1.438 (5) | C10—C11 | 1.385 (5) |
C1—C5 | 1.470 (4) | C10—H10 | 0.9300 |
C2—C3 | 1.331 (5) | C11—C12 | 1.385 (5) |
C2—H2 | 0.9300 | C11—H11 | 0.9300 |
C3—H3 | 0.9300 | C12—H12 | 0.9300 |
C4—C13 | 1.480 (6) | C13—H13A | 0.9600 |
C6—C7 | 1.520 (4) | C13—H13B | 0.9600 |
C6—H6A | 0.9700 | C13—H13C | 0.9600 |
| | | |
C5—N—C6 | 124.6 (3) | C12—C7—C8 | 118.8 (3) |
C5—N—H1N | 122 (3) | C12—C7—C6 | 122.8 (3) |
C6—N—H1N | 114 (3) | C8—C7—C6 | 118.3 (3) |
C4—O—C3 | 107.4 (3) | C9—C8—C7 | 121.2 (3) |
C4—C1—C2 | 105.9 (3) | C9—C8—H8 | 119.4 |
C4—C1—C5 | 127.8 (3) | C7—C8—H8 | 119.4 |
C2—C1—C5 | 126.3 (3) | C8—C9—C10 | 119.6 (3) |
C3—C2—C1 | 107.3 (4) | C8—C9—H9 | 120.2 |
C3—C2—H2 | 126.3 | C10—C9—H9 | 120.2 |
C1—C2—H2 | 126.3 | C9—C10—C11 | 119.9 (4) |
C2—C3—O | 110.0 (4) | C9—C10—H10 | 120.1 |
C2—C3—H3 | 125.0 | C11—C10—H10 | 120.1 |
O—C3—H3 | 125.0 | C12—C11—C10 | 120.2 (3) |
O—C4—C1 | 109.4 (4) | C12—C11—H11 | 119.9 |
O—C4—C13 | 115.1 (3) | C10—C11—H11 | 119.9 |
C1—C4—C13 | 135.5 (4) | C11—C12—C7 | 120.3 (3) |
N—C5—C1 | 114.6 (3) | C11—C12—H12 | 119.9 |
N—C5—S1 | 122.2 (2) | C7—C12—H12 | 119.9 |
C1—C5—S1 | 123.2 (2) | C4—C13—H13A | 109.5 |
N—C6—C7 | 114.9 (3) | C4—C13—H13B | 109.5 |
N—C6—H6A | 108.5 | H13A—C13—H13B | 109.5 |
C7—C6—H6A | 108.5 | C4—C13—H13C | 109.5 |
N—C6—H6B | 108.5 | H13A—C13—H13C | 109.5 |
C7—C6—H6B | 108.5 | H13B—C13—H13C | 109.5 |
H6A—C6—H6B | 107.5 | | |
| | | |
C4—C1—C2—C3 | −0.1 (4) | C4—C1—C5—S1 | 20.0 (5) |
C5—C1—C2—C3 | −178.9 (4) | C2—C1—C5—S1 | −161.5 (3) |
C1—C2—C3—O | 0.7 (5) | C5—N—C6—C7 | 85.5 (4) |
C4—O—C3—C2 | −1.0 (5) | N—C6—C7—C12 | 5.2 (4) |
C3—O—C4—C1 | 0.9 (4) | N—C6—C7—C8 | −176.7 (3) |
C3—O—C4—C13 | 179.6 (3) | C12—C7—C8—C9 | 0.4 (5) |
C2—C1—C4—O | −0.5 (4) | C6—C7—C8—C9 | −177.7 (3) |
C5—C1—C4—O | 178.2 (3) | C7—C8—C9—C10 | −0.7 (6) |
C2—C1—C4—C13 | −178.8 (4) | C8—C9—C10—C11 | 0.5 (6) |
C5—C1—C4—C13 | −0.1 (7) | C9—C10—C11—C12 | 0.0 (6) |
C6—N—C5—C1 | −178.2 (3) | C10—C11—C12—C7 | −0.2 (5) |
C6—N—C5—S1 | 1.2 (4) | C8—C7—C12—C11 | 0.0 (5) |
C4—C1—C5—N | −160.5 (3) | C6—C7—C12—C11 | 178.0 (3) |
C2—C1—C5—N | 17.9 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N—H1N···S1i | 0.85 (5) | 2.71 (5) | 3.444 (3) | 145 (4) |
Symmetry code: (i) −x+1, y+1/2, −z−1/2. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.