The title compound, C15H17NO2S, synthesized as an inhibitor for 5-lipoxygenase, comprises the neutral 1,2-diethyl-3-hydroxy-6-phenylthiopyridin-4(1H)-one molecule. The H atom of the hydroxy group and the carbonyl O atom form intermolecular hydrogen bonds with another molecule in a head-to-head fashion. The resulting dimers pack along the b axis and form hydrophobic channels.
Supporting information
CCDC reference: 180799
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.047
- wR factor = 0.127
- Data-to-parameter ratio = 16.4
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT-Plus (Bruker,1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
1,2–diethyl–3–hydroxy–6–phenylthio–4(1
H)–pyridinone
top
Crystal data top
C15H17NO2S | F(000) = 584 |
Mr = 275.36 | Dx = 1.247 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 12.980 (7) Å | Cell parameters from 820 reflections |
b = 8.482 (5) Å | θ = 3.0–26.6° |
c = 14.189 (8) Å | µ = 0.22 mm−1 |
β = 110.165 (9)° | T = 293 K |
V = 1466.4 (14) Å3 | Block, colorless |
Z = 4 | 0.46 × 0.26 × 0.20 mm |
Data collection top
Bruker CCD area-detector diffractometer | 3200 independent reflections |
Radiation source: fine-focus sealed tube | 2277 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
φ and ω scans | θmax = 27.2°, θmin = 1.8° |
Absorption correction: empirical (using intensity measurements) (Blessing, 1995) | h = −16→16 |
Tmin = 0.906, Tmax = 0.958 | k = −10→6 |
8374 measured reflections | l = −18→17 |
Refinement top
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)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.0454P)2 + 0.6466P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
3200 reflections | Δρmax = 0.27 e Å−3 |
195 parameters | Δρmin = −0.31 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: 0.016 (2) |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
S1 | 1.00764 (5) | 0.52846 (8) | 0.17086 (4) | 0.0713 (3) | |
O1 | 0.87389 (15) | −0.0160 (2) | 0.35630 (12) | 0.0804 (6) | |
H1A | 0.913 (2) | −0.028 (3) | 0.417 (2) | 0.092 (9)* | |
O2 | 1.05678 (12) | 0.14881 (19) | 0.46458 (10) | 0.0659 (5) | |
N1 | 0.88379 (13) | 0.28094 (19) | 0.17750 (11) | 0.0477 (4) | |
C1 | 0.97479 (15) | 0.3628 (2) | 0.23201 (13) | 0.0452 (4) | |
C2 | 1.03476 (16) | 0.3194 (2) | 0.32786 (14) | 0.0515 (5) | |
H2A | 1.0972 | 0.3770 | 0.3628 | 0.062* | |
C3 | 1.00525 (15) | 0.1905 (2) | 0.37555 (13) | 0.0452 (5) | |
C4 | 0.90904 (16) | 0.1085 (2) | 0.31589 (14) | 0.0501 (5) | |
C5 | 0.84951 (19) | 0.1533 (3) | 0.22063 (15) | 0.0649 (7) | |
C6A | 0.7316 (4) | 0.0849 (5) | 0.1704 (2) | 0.0614 (9) | 0.70 |
H6AA | 0.7016 | 0.0540 | 0.2216 | 0.074* | 0.70 |
H6AB | 0.6838 | 0.1642 | 0.1281 | 0.074* | 0.70 |
C7A | 0.7384 (5) | −0.0545 (6) | 0.1091 (4) | 0.1141 (19) | 0.70 |
H7AA | 0.6664 | −0.0981 | 0.0776 | 0.171* | 0.70 |
H7AB | 0.7855 | −0.1326 | 0.1516 | 0.171* | 0.70 |
H7AC | 0.7677 | −0.0227 | 0.0584 | 0.171* | 0.70 |
C6B | 0.7837 (7) | 0.0204 (10) | 0.1469 (5) | 0.0455 (15) | 0.30 |
H6BA | 0.7892 | 0.0313 | 0.0808 | 0.055* | 0.30 |
H6BB | 0.8081 | −0.0841 | 0.1730 | 0.055* | 0.30 |
C7B | 0.6650 (7) | 0.0559 (12) | 0.1456 (7) | 0.075 (3) | 0.30 |
H7BA | 0.6145 | −0.0181 | 0.1024 | 0.113* | 0.30 |
H7BB | 0.6444 | 0.1610 | 0.1213 | 0.113* | 0.30 |
H7BC | 0.6630 | 0.0465 | 0.2124 | 0.113* | 0.30 |
C8 | 1.11667 (18) | 0.6178 (3) | 0.26866 (16) | 0.0556 (5) | |
C9 | 1.22400 (19) | 0.5806 (3) | 0.28120 (17) | 0.0623 (6) | |
H9A | 1.2393 | 0.5052 | 0.2403 | 0.075* | |
C10 | 1.3085 (2) | 0.6551 (3) | 0.35430 (19) | 0.0716 (7) | |
H10A | 1.3809 | 0.6302 | 0.3626 | 0.086* | |
C11 | 1.2861 (2) | 0.7658 (3) | 0.4148 (2) | 0.0803 (8) | |
H11A | 1.3434 | 0.8151 | 0.4646 | 0.096* | |
C12 | 1.1796 (3) | 0.8042 (3) | 0.4020 (2) | 0.0876 (9) | |
H12A | 1.1648 | 0.8801 | 0.4428 | 0.105* | |
C13 | 1.0945 (2) | 0.7308 (3) | 0.3289 (2) | 0.0744 (7) | |
H13A | 1.0223 | 0.7573 | 0.3202 | 0.089* | |
C14 | 0.82214 (17) | 0.3256 (3) | 0.07217 (14) | 0.0575 (6) | |
H14A | 0.8215 | 0.4395 | 0.0664 | 0.069* | |
H14B | 0.7467 | 0.2905 | 0.0547 | 0.069* | |
C15 | 0.8704 (2) | 0.2558 (4) | −0.00098 (17) | 0.0857 (9) | |
H15A | 0.8277 | 0.2884 | −0.0679 | 0.129* | |
H15B | 0.8695 | 0.1429 | 0.0032 | 0.129* | |
H15C | 0.9446 | 0.2917 | 0.0151 | 0.129* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0720 (4) | 0.0719 (4) | 0.0526 (3) | −0.0274 (3) | −0.0009 (3) | 0.0239 (3) |
O1 | 0.0855 (12) | 0.0823 (12) | 0.0468 (9) | −0.0437 (10) | −0.0110 (8) | 0.0263 (8) |
O2 | 0.0636 (9) | 0.0736 (10) | 0.0408 (8) | −0.0214 (8) | −0.0071 (7) | 0.0208 (7) |
N1 | 0.0456 (9) | 0.0519 (10) | 0.0357 (8) | −0.0083 (7) | 0.0015 (7) | 0.0110 (7) |
C1 | 0.0413 (10) | 0.0476 (11) | 0.0409 (10) | −0.0036 (8) | 0.0069 (8) | 0.0071 (8) |
C2 | 0.0459 (11) | 0.0550 (12) | 0.0419 (10) | −0.0146 (9) | 0.0003 (8) | 0.0103 (9) |
C3 | 0.0427 (10) | 0.0499 (11) | 0.0352 (9) | −0.0031 (8) | 0.0033 (8) | 0.0073 (8) |
C4 | 0.0535 (11) | 0.0486 (11) | 0.0390 (10) | −0.0126 (9) | 0.0043 (8) | 0.0101 (8) |
C5 | 0.0675 (14) | 0.0660 (14) | 0.0421 (11) | −0.0275 (11) | −0.0055 (10) | 0.0151 (10) |
C6A | 0.059 (2) | 0.070 (2) | 0.0433 (18) | −0.015 (2) | 0.0018 (18) | 0.0126 (17) |
C7A | 0.142 (5) | 0.110 (4) | 0.097 (3) | −0.066 (4) | 0.050 (3) | −0.043 (3) |
C6B | 0.054 (4) | 0.041 (4) | 0.030 (3) | −0.011 (3) | 0.000 (3) | −0.002 (3) |
C7B | 0.047 (5) | 0.090 (7) | 0.079 (6) | −0.028 (5) | 0.009 (4) | 0.008 (5) |
C8 | 0.0590 (13) | 0.0487 (12) | 0.0543 (12) | −0.0124 (10) | 0.0134 (10) | 0.0116 (10) |
C9 | 0.0676 (15) | 0.0585 (13) | 0.0601 (13) | −0.0088 (11) | 0.0210 (11) | −0.0006 (11) |
C10 | 0.0570 (14) | 0.0762 (17) | 0.0753 (16) | −0.0134 (12) | 0.0149 (12) | 0.0003 (13) |
C11 | 0.0804 (19) | 0.0747 (17) | 0.0768 (17) | −0.0257 (14) | 0.0156 (14) | −0.0142 (14) |
C12 | 0.097 (2) | 0.0737 (18) | 0.094 (2) | −0.0177 (16) | 0.0352 (17) | −0.0269 (15) |
C13 | 0.0676 (15) | 0.0673 (16) | 0.0893 (18) | −0.0038 (13) | 0.0281 (14) | 0.0012 (14) |
C14 | 0.0490 (12) | 0.0690 (14) | 0.0407 (11) | −0.0096 (10) | −0.0023 (9) | 0.0192 (10) |
C15 | 0.0914 (19) | 0.116 (2) | 0.0444 (13) | −0.0185 (17) | 0.0170 (13) | 0.0051 (14) |
Geometric parameters (Å, º) top
S1—C8 | 1.775 (2) | C6B—H6BA | 0.9700 |
S1—C1 | 1.779 (2) | C6B—H6BB | 0.9700 |
O1—C4 | 1.354 (2) | C7B—H7BA | 0.9600 |
O1—H1A | 0.84 (3) | C7B—H7BB | 0.9600 |
O2—C3 | 1.259 (2) | C7B—H7BC | 0.9600 |
N1—C1 | 1.358 (2) | C8—C13 | 1.379 (3) |
N1—C5 | 1.390 (3) | C8—C9 | 1.379 (3) |
N1—C14 | 1.481 (2) | C9—C10 | 1.376 (3) |
C1—C2 | 1.364 (3) | C9—H9A | 0.9300 |
C2—C3 | 1.406 (3) | C10—C11 | 1.369 (4) |
C2—H2A | 0.9300 | C10—H10A | 0.9300 |
C3—C4 | 1.425 (3) | C11—C12 | 1.370 (4) |
C4—C5 | 1.359 (3) | C11—H11A | 0.9300 |
C5—C6A | 1.561 (4) | C12—C13 | 1.376 (4) |
C5—C6B | 1.574 (8) | C12—H12A | 0.9300 |
C6A—C7A | 1.489 (6) | C13—H13A | 0.9300 |
C6A—H6AA | 0.9700 | C14—C15 | 1.505 (3) |
C6A—H6AB | 0.9700 | C14—H14A | 0.9700 |
C7A—H7AA | 0.9600 | C14—H14B | 0.9700 |
C7A—H7AB | 0.9600 | C15—H15A | 0.9600 |
C7A—H7AC | 0.9600 | C15—H15B | 0.9600 |
C6B—C7B | 1.565 (12) | C15—H15C | 0.9600 |
| | | |
C8—S1—C1 | 102.52 (9) | C5—C6B—H6BB | 111.7 |
C4—O1—H1A | 111 (2) | H6BA—C6B—H6BB | 109.5 |
C1—N1—C5 | 119.65 (15) | C6B—C7B—H7BA | 109.5 |
C1—N1—C14 | 120.36 (16) | C6B—C7B—H7BB | 109.5 |
C5—N1—C14 | 119.99 (16) | H7BA—C7B—H7BB | 109.5 |
N1—C1—C2 | 121.02 (17) | C6B—C7B—H7BC | 109.5 |
N1—C1—S1 | 115.68 (13) | H7BA—C7B—H7BC | 109.5 |
C2—C1—S1 | 123.29 (15) | H7BB—C7B—H7BC | 109.5 |
C1—C2—C3 | 122.19 (17) | C13—C8—C9 | 119.8 (2) |
C1—C2—H2A | 118.9 | C13—C8—S1 | 120.07 (19) |
C3—C2—H2A | 118.9 | C9—C8—S1 | 120.07 (19) |
O2—C3—C2 | 124.23 (17) | C10—C9—C8 | 120.0 (2) |
O2—C3—C4 | 120.82 (17) | C10—C9—H9A | 120.0 |
C2—C3—C4 | 114.94 (16) | C8—C9—H9A | 120.0 |
O1—C4—C5 | 118.68 (18) | C11—C10—C9 | 120.1 (3) |
O1—C4—C3 | 118.91 (16) | C11—C10—H10A | 120.0 |
C5—C4—C3 | 122.39 (18) | C9—C10—H10A | 120.0 |
C4—C5—N1 | 119.79 (18) | C10—C11—C12 | 120.1 (2) |
C4—C5—C6A | 118.8 (2) | C10—C11—H11A | 119.9 |
N1—C5—C6A | 120.07 (19) | C12—C11—H11A | 119.9 |
C4—C5—C6B | 116.9 (3) | C11—C12—C13 | 120.3 (3) |
N1—C5—C6B | 116.6 (3) | C11—C12—H12A | 119.9 |
C6A—C5—C6B | 37.7 (3) | C13—C12—H12A | 119.9 |
C7A—C6A—C5 | 108.4 (5) | C12—C13—C8 | 119.8 (3) |
C7A—C6A—H6AA | 110.0 | C12—C13—H13A | 120.1 |
C5—C6A—H6AA | 110.0 | C8—C13—H13A | 120.1 |
C7A—C6A—H6AB | 110.0 | N1—C14—C15 | 112.77 (19) |
C5—C6A—H6AB | 110.0 | N1—C14—H14A | 109.0 |
H6AA—C6A—H6AB | 108.4 | C15—C14—H14A | 109.0 |
C6A—C7A—H7AA | 109.5 | N1—C14—H14B | 109.0 |
C6A—C7A—H7AB | 109.5 | C15—C14—H14B | 109.0 |
H7AA—C7A—H7AB | 109.5 | H14A—C14—H14B | 107.8 |
C6A—C7A—H7AC | 109.5 | C14—C15—H15A | 109.5 |
H7AA—C7A—H7AC | 109.5 | C14—C15—H15B | 109.5 |
H7AB—C7A—H7AC | 109.5 | H15A—C15—H15B | 109.5 |
C7B—C6B—C5 | 100.2 (8) | C14—C15—H15C | 109.5 |
C7B—C6B—H6BA | 111.7 | H15A—C15—H15C | 109.5 |
C5—C6B—H6BA | 111.7 | H15B—C15—H15C | 109.5 |
C7B—C6B—H6BB | 111.7 | | |
| | | |
C5—N1—C1—C2 | 1.6 (3) | C1—N1—C5—C6A | 164.7 (3) |
C14—N1—C1—C2 | −177.5 (2) | C14—N1—C5—C6A | −16.2 (4) |
C5—N1—C1—S1 | −177.54 (17) | C1—N1—C5—C6B | −152.4 (4) |
C14—N1—C1—S1 | 3.4 (3) | C14—N1—C5—C6B | 26.7 (5) |
C8—S1—C1—N1 | 172.43 (16) | C4—C5—C6A—C7A | −95.5 (4) |
C8—S1—C1—C2 | −6.6 (2) | N1—C5—C6A—C7A | 97.7 (4) |
N1—C1—C2—C3 | −0.9 (3) | C6B—C5—C6A—C7A | 2.1 (5) |
S1—C1—C2—C3 | 178.12 (16) | C4—C5—C6B—C7B | 103.6 (5) |
C1—C2—C3—O2 | −178.3 (2) | N1—C5—C6B—C7B | −105.1 (5) |
C1—C2—C3—C4 | 0.6 (3) | C6A—C5—C6B—C7B | 0.4 (4) |
O2—C3—C4—O1 | −0.3 (3) | C1—S1—C8—C13 | −90.1 (2) |
C2—C3—C4—O1 | −179.2 (2) | C1—S1—C8—C9 | 93.32 (19) |
O2—C3—C4—C5 | 177.9 (2) | C13—C8—C9—C10 | 0.6 (3) |
C2—C3—C4—C5 | −1.0 (3) | S1—C8—C9—C10 | 177.20 (18) |
O1—C4—C5—N1 | 179.9 (2) | C8—C9—C10—C11 | 0.2 (4) |
C3—C4—C5—N1 | 1.7 (4) | C9—C10—C11—C12 | −0.8 (4) |
O1—C4—C5—C6A | 13.1 (4) | C10—C11—C12—C13 | 0.6 (5) |
C3—C4—C5—C6A | −165.1 (3) | C11—C12—C13—C8 | 0.2 (4) |
O1—C4—C5—C6B | −29.7 (5) | C9—C8—C13—C12 | −0.8 (4) |
C3—C4—C5—C6B | 152.0 (4) | S1—C8—C13—C12 | −177.4 (2) |
C1—N1—C5—C4 | −1.9 (3) | C1—N1—C14—C15 | 83.6 (3) |
C14—N1—C5—C4 | 177.1 (2) | C5—N1—C14—C15 | −95.5 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2i | 0.84 (3) | 1.89 (3) | 2.638 (2) | 147 (3) |
O1—H1A···O2 | 0.84 (3) | 2.31 (3) | 2.727 (2) | 111 (2) |
Symmetry code: (i) −x+2, −y, −z+1. |