Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680101008X/ci6036sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680101008X/ci6036Isup2.hkl |
CCDC reference: 170774
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- R factor = 0.038
- wR factor = 0.099
- Data-to-parameter ratio = 17.8
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
The title compound was obtained by addition of the potassium salt of (4-methoxyphenyl)methane-1-thiol to 4-fluorobenzaldehyde. The product was recrystallized from ethyl acetate/hexane; m.p. 377–378 K. 1H NMR (CDCl3, 300 MHz): δ 3.80, s, 3H; 4.20, s, 2H; 6.86, d, J 8.7 Hz, 2H; 7.30, d, J 9.0 Hz, 2H; 7.37, d, J 8.4 Hz, 2H; 7.75, d, J 8.7 Hz, 2H; 9.91, s, 1H.
The C-bound H atoms were placed in geometrically calculated positions and included in the final refinement in the riding-model approximation with an overall displacement parameter.
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1996); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.
Fig. 1. The molecular structure and crystallographic numbering scheme for (I). Displacement ellipsoids are shown at the 50% probability level (Johnson, 1976). |
C15H14O2S | F(000) = 544 |
Mr = 258.33 | Dx = 1.345 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2yn | Cell parameters from 21 reflections |
a = 7.648 (3) Å | θ = 8.4–13.4° |
b = 6.872 (6) Å | µ = 0.24 mm−1 |
c = 24.314 (2) Å | T = 173 K |
β = 93.10 (2)° | Plate, colourless |
V = 1276.0 (12) Å3 | 0.40 × 0.32 × 0.03 mm |
Z = 4 |
Rigaku AFC-7R diffractometer | Rint = 0.064 |
Radiation source: Rigaku rotating anode | θmax = 27.5°, θmin = 3.1° |
Graphite monochromator | h = −9→9 |
ω scans | k = 0→8 |
6267 measured reflections | l = 0→31 |
2921 independent reflections | 3 standard reflections every 400 reflections |
1671 reflections with I > 2σ(I) | intensity decay: −1.2% |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0401P)2] where P = (Fo2 + 2Fc2)/3 |
2921 reflections | (Δ/σ)max < 0.001 |
164 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
C15H14O2S | V = 1276.0 (12) Å3 |
Mr = 258.33 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.648 (3) Å | µ = 0.24 mm−1 |
b = 6.872 (6) Å | T = 173 K |
c = 24.314 (2) Å | 0.40 × 0.32 × 0.03 mm |
β = 93.10 (2)° |
Rigaku AFC-7R diffractometer | Rint = 0.064 |
6267 measured reflections | 3 standard reflections every 400 reflections |
2921 independent reflections | intensity decay: −1.2% |
1671 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.26 e Å−3 |
2921 reflections | Δρmin = −0.26 e Å−3 |
164 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 | ||
S4 | 0.07660 (7) | 0.66559 (9) | 0.451215 (19) | 0.03843 (16) | |
O11 | 0.7886 (2) | 0.8163 (3) | 0.62435 (6) | 0.0542 (4) | |
O45 | −0.58167 (17) | 0.6666 (2) | 0.28187 (6) | 0.0444 (4) | |
C1 | 0.5984 (3) | 0.7729 (3) | 0.54431 (8) | 0.0331 (5) | |
C2 | 0.5914 (3) | 0.7668 (3) | 0.48715 (8) | 0.0338 (5) | |
H2 | 0.6957 | 0.7860 | 0.4683 | 0.0412 (16)* | |
C3 | 0.4367 (3) | 0.7335 (3) | 0.45742 (8) | 0.0330 (5) | |
H3 | 0.4347 | 0.7276 | 0.4184 | 0.0412 (16)* | |
C4 | 0.2824 (3) | 0.7084 (3) | 0.48455 (7) | 0.0300 (4) | |
C5 | 0.2877 (3) | 0.7141 (3) | 0.54238 (7) | 0.0336 (5) | |
H5 | 0.1832 | 0.6965 | 0.5612 | 0.0412 (16)* | |
C6 | 0.4439 (3) | 0.7450 (3) | 0.57159 (8) | 0.0341 (5) | |
H6 | 0.4471 | 0.7476 | 0.6107 | 0.0412 (16)* | |
C11 | 0.7660 (3) | 0.8110 (3) | 0.57467 (9) | 0.0427 (5) | |
H11 | 0.8650 | 0.8336 | 0.5536 | 0.0412 (16)* | |
C41 | 0.1102 (3) | 0.6878 (3) | 0.37787 (7) | 0.0354 (5) | |
H41A | 0.1683 | 0.8126 | 0.3699 | 0.0412 (16)* | |
H41B | 0.1835 | 0.5796 | 0.3652 | 0.0412 (16)* | |
C42 | −0.0711 (2) | 0.6798 (3) | 0.34977 (7) | 0.0332 (5) | |
C43 | −0.1315 (3) | 0.5118 (3) | 0.32327 (8) | 0.0379 (5) | |
H43 | −0.0560 | 0.4025 | 0.3213 | 0.0412 (16)* | |
C44 | −0.3018 (3) | 0.5014 (3) | 0.29952 (7) | 0.0374 (5) | |
H44 | −0.3415 | 0.3860 | 0.2813 | 0.0412 (16)* | |
C45 | −0.4120 (2) | 0.6594 (3) | 0.30274 (7) | 0.0343 (5) | |
C46 | −0.3519 (3) | 0.8297 (3) | 0.32859 (7) | 0.0385 (5) | |
H46 | −0.4269 | 0.9394 | 0.3303 | 0.0412 (16)* | |
C47 | −0.1830 (3) | 0.8383 (3) | 0.35165 (7) | 0.0362 (5) | |
H47 | −0.1428 | 0.9548 | 0.3691 | 0.0412 (16)* | |
C48 | −0.6549 (3) | 0.4943 (4) | 0.25854 (9) | 0.0478 (6) | |
H48A | −0.7763 | 0.5190 | 0.2454 | 0.0412 (16)* | |
H48B | −0.6525 | 0.3914 | 0.2865 | 0.0412 (16)* | |
H48C | −0.5867 | 0.4531 | 0.2276 | 0.0412 (16)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S4 | 0.0334 (2) | 0.0539 (4) | 0.0283 (2) | −0.0054 (3) | 0.00475 (18) | 0.0024 (3) |
O11 | 0.0606 (10) | 0.0511 (11) | 0.0489 (9) | −0.0040 (9) | −0.0144 (8) | −0.0030 (8) |
O45 | 0.0394 (8) | 0.0484 (10) | 0.0446 (8) | 0.0017 (8) | −0.0035 (6) | −0.0051 (8) |
C1 | 0.0372 (11) | 0.0227 (11) | 0.0392 (10) | 0.0004 (9) | 0.0005 (9) | −0.0020 (9) |
C2 | 0.0340 (11) | 0.0274 (11) | 0.0408 (11) | 0.0042 (9) | 0.0078 (9) | 0.0015 (9) |
C3 | 0.0396 (11) | 0.0302 (11) | 0.0297 (9) | 0.0043 (9) | 0.0075 (8) | 0.0014 (9) |
C4 | 0.0352 (10) | 0.0250 (11) | 0.0297 (9) | 0.0015 (9) | 0.0026 (8) | 0.0007 (8) |
C5 | 0.0369 (11) | 0.0328 (12) | 0.0319 (10) | −0.0006 (9) | 0.0079 (8) | 0.0007 (9) |
C6 | 0.0451 (12) | 0.0279 (11) | 0.0293 (10) | −0.0010 (10) | 0.0030 (9) | −0.0022 (9) |
C11 | 0.0427 (11) | 0.0315 (12) | 0.0534 (13) | 0.0002 (11) | −0.0033 (10) | −0.0033 (11) |
C41 | 0.0386 (10) | 0.0409 (12) | 0.0273 (9) | −0.0038 (10) | 0.0067 (8) | 0.0006 (9) |
C42 | 0.0388 (10) | 0.0388 (12) | 0.0225 (8) | −0.0036 (11) | 0.0060 (7) | 0.0032 (9) |
C43 | 0.0424 (11) | 0.0382 (13) | 0.0338 (10) | 0.0009 (10) | 0.0068 (9) | −0.0034 (9) |
C44 | 0.0455 (12) | 0.0368 (12) | 0.0303 (10) | −0.0040 (11) | 0.0056 (9) | −0.0079 (10) |
C45 | 0.0372 (10) | 0.0418 (12) | 0.0242 (8) | −0.0034 (11) | 0.0047 (8) | 0.0006 (10) |
C46 | 0.0475 (12) | 0.0357 (12) | 0.0329 (10) | 0.0023 (12) | 0.0058 (9) | −0.0007 (10) |
C47 | 0.0469 (11) | 0.0333 (12) | 0.0285 (9) | −0.0047 (11) | 0.0012 (8) | −0.0011 (10) |
C48 | 0.0415 (12) | 0.0592 (17) | 0.0423 (12) | −0.0025 (12) | −0.0012 (10) | −0.0083 (12) |
S4—C4 | 1.756 (2) | C4—C5 | 1.405 (2) |
S4—C41 | 1.8218 (18) | C5—C6 | 1.373 (3) |
O11—C11 | 1.212 (2) | C41—C42 | 1.513 (3) |
O45—C45 | 1.369 (2) | C42—C47 | 1.387 (3) |
O45—C48 | 1.416 (3) | C42—C43 | 1.389 (3) |
C1—C2 | 1.389 (3) | C43—C44 | 1.398 (3) |
C1—C6 | 1.400 (3) | C44—C45 | 1.379 (3) |
C1—C11 | 1.467 (3) | C45—C46 | 1.394 (3) |
C2—C3 | 1.372 (3) | C46—C47 | 1.381 (3) |
C3—C4 | 1.393 (3) | ||
C4—S4—C41 | 105.51 (9) | O11—C11—C1 | 125.5 (2) |
C45—O45—C48 | 117.70 (17) | C42—C41—S4 | 105.33 (12) |
C2—C1—C6 | 118.84 (18) | C47—C42—C43 | 118.54 (19) |
C2—C1—C11 | 119.6 (2) | C47—C42—C41 | 120.57 (19) |
C6—C1—C11 | 121.53 (18) | C43—C42—C41 | 120.85 (19) |
C1—C2—C3 | 121.18 (19) | C42—C43—C44 | 120.9 (2) |
C2—C3—C4 | 119.97 (17) | C45—C44—C43 | 119.6 (2) |
C3—C4—C5 | 119.43 (18) | O45—C45—C44 | 125.3 (2) |
C3—C4—S4 | 124.28 (15) | O45—C45—C46 | 114.80 (19) |
C5—C4—S4 | 116.29 (15) | C44—C45—C46 | 119.93 (19) |
C6—C5—C4 | 119.93 (18) | C47—C46—C45 | 119.8 (2) |
C5—C6—C1 | 120.64 (17) | C46—C47—C42 | 121.2 (2) |
Experimental details
Crystal data | |
Chemical formula | C15H14O2S |
Mr | 258.33 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 7.648 (3), 6.872 (6), 24.314 (2) |
β (°) | 93.10 (2) |
V (Å3) | 1276.0 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.40 × 0.32 × 0.03 |
Data collection | |
Diffractometer | Rigaku AFC-7R diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6267, 2921, 1671 |
Rint | 0.064 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.099, 0.97 |
No. of reflections | 2921 |
No. of parameters | 164 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.26 |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1996), MSC/AFC Diffractometer Control Software, TEXSAN for Windows (Molecular Structure Corporation, 1997), SIR97 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), SHELXL97.
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
The title compound, (I) (Fig. 1), adopts an extended conformation as seen in the value of the C4—S4—C41—C42 torsion angle of -172.08 (14)°. The dihedral angle between the least-squares plane through the two aromatic rings is 72.52 (9)°. The observed molecular conformation allows for the formation of columns of molecules, running parallel to b, that are stabilized by π···π interactions occurring between the C1—C6 aromatic rings. Within the columns, the closest contact between the ring centroids of 3.508 (3) Å occurs between centrosymmetrically related molecules (symmetry code: 1 - x, 1 - y, 1 - z). This pair of molecules forms weaker π···π interactions to adjacent pairs so that the separation between the ring centroids is 3.764 (3) Å (symmetry code: 1 - x, 2 - y, 1 - z). Additional stabilization within the columns is provided by C—H···O contacts so that H41A···O11 is 2.57 Å, C41···O11 is 3.496 (4) Å and the angle at H41A is 155° (symmetry code: 1 - x, 2 - y, 1 - z). Links between the columns are afforded by C—H···π contacts involving H44 and the second aromatic ring C42—C47 at -1/2 - x, -1/2 + y, 1/2 - z with a H44···ring centroid distance of 3.10 Å and the angle at H44 of 136°.