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The title compound, C26H23F2NO3S, a polysubstituted piperidine enol, adopts a twisted half-chair conformation. The crystal structure is stabilized by N—H...F, C—H...O and weak C—H...π inter­actions. An intra­molecular O—H...S inter­action generates an S(5) graph-set motif.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807007179/dn2130sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807007179/dn2130Isup2.hkl
Contains datablock I

CCDC reference: 640318

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.079
  • wR factor = 0.279
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for O1 - C4 .. 7.75 su
Alert level C RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.279 RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.115 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT084_ALERT_2_C High R2 Value .................................. 0.28 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C55 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C51 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97.

(2RS,5SR,6SR)-Ethyl 2,6-bis(4-fluorophenyl)-4-hydroxy-5-phenylsulfanyl- 1,2,5,6-tetrahydropyridine-3-carboxylate top
Crystal data top
C26H23F2NO3SF(000) = 976
Mr = 467.51Dx = 1.338 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 18.3565 (11) Åθ = 2–25°
b = 5.7293 (7) ŵ = 0.18 mm1
c = 22.1286 (13) ÅT = 293 K
β = 94.242 (18)°Block, colourless
V = 2320.9 (3) Å30.20 × 0.16 × 0.13 mm
Z = 4
Data collection top
Nonius MACH-3 four-circle
diffractometer
2176 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.115
Graphite monochromatorθmax = 25.0°, θmin = 2.1°
ω scansh = 021
Absorption correction: ψ scan
(North et al., 1968)
k = 16
Tmin = 0.965, Tmax = 0.976l = 2626
5106 measured reflections3 standard reflections every 60 min
4074 independent reflections
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)] = 0.079Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.279H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.1375P)2 + 2.5931P]
where P = (Fo2 + 2Fc2)/3
4074 reflections(Δ/σ)max = 0.001
304 parametersΔρmax = 0.55 e Å3
0 restraintsΔρmin = 0.51 e Å3
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
xyzUiso*/Ueq
C20.1699 (3)0.8878 (10)0.3453 (2)0.0442 (13)
H20.18190.73240.36170.053*
C30.2088 (3)1.0735 (10)0.3850 (2)0.0454 (13)
C40.2621 (3)1.2118 (10)0.3654 (2)0.0458 (13)
C50.2929 (3)1.1716 (10)0.3045 (2)0.0488 (13)
H50.26891.28480.27640.059*
C60.2728 (3)0.9295 (10)0.2795 (2)0.0458 (13)
H60.29840.80930.30440.055*
C70.1877 (3)1.0940 (11)0.4471 (2)0.0540 (15)
C80.1241 (4)0.9219 (13)0.5245 (2)0.073 (2)
H8A0.09741.06500.53060.088*
H8B0.16540.91430.55450.088*
C90.0750 (5)0.7113 (15)0.5296 (3)0.101 (3)
H9A0.03870.70970.49610.152*
H9B0.05160.71930.56690.152*
H9C0.10380.57140.52900.152*
C210.0883 (3)0.9207 (9)0.3400 (2)0.0415 (12)
C220.0574 (3)1.1226 (9)0.3142 (2)0.0453 (13)
H220.08801.24090.30230.054*
C230.0169 (3)1.1522 (10)0.3060 (2)0.0504 (14)
H230.03661.28800.28850.060*
C240.0615 (3)0.9772 (10)0.3240 (2)0.0490 (14)
C250.0342 (3)0.7767 (10)0.3502 (2)0.0524 (14)
H250.06540.66120.36270.063*
C260.0406 (3)0.7484 (9)0.3578 (2)0.0463 (13)
H260.05960.61170.37530.056*
C510.4332 (3)0.9950 (11)0.3479 (2)0.0496 (14)
C520.4845 (3)0.8594 (12)0.3202 (3)0.0624 (17)
H520.49250.88630.27980.075*
C530.5235 (4)0.6870 (14)0.3514 (3)0.078 (2)
H530.55810.60060.33240.094*
C540.5110 (4)0.6437 (15)0.4103 (3)0.082 (2)
H540.53710.52750.43180.099*
C550.4593 (4)0.7731 (17)0.4381 (3)0.101 (3)
H560.44980.74070.47800.121*
C560.4218 (4)0.9489 (15)0.4073 (3)0.082 (2)
H360.38831.03780.42690.098*
C610.2885 (3)0.8989 (10)0.2135 (2)0.0471 (13)
C620.3318 (3)0.7199 (10)0.1953 (3)0.0531 (14)
H620.35400.61990.22420.064*
C630.3429 (4)0.6862 (12)0.1351 (3)0.0660 (18)
H630.37220.56460.12330.079*
C640.3106 (3)0.8316 (13)0.0937 (2)0.0636 (17)
C650.2674 (4)1.0156 (13)0.1090 (3)0.0692 (18)
H650.24611.11530.07960.083*
C660.2570 (3)1.0466 (12)0.1699 (3)0.0620 (17)
H660.22811.16970.18160.074*
F10.13491 (17)1.0058 (7)0.31601 (17)0.0719 (11)
F20.3216 (2)0.8027 (9)0.03380 (15)0.0949 (15)
N10.1935 (2)0.9068 (10)0.2834 (2)0.0492 (12)
O10.2906 (3)1.3996 (9)0.3975 (2)0.0852 (15)
H1A0.32941.43800.38430.128*
O20.2034 (3)1.2562 (9)0.48133 (18)0.0767 (14)
O30.1485 (2)0.9132 (7)0.46397 (15)0.0593 (11)
S10.39135 (8)1.2276 (3)0.30535 (7)0.0577 (5)
H10.179 (3)0.802 (11)0.258 (3)0.06 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.052 (3)0.048 (3)0.035 (2)0.001 (3)0.017 (2)0.000 (2)
C30.046 (3)0.051 (3)0.040 (3)0.002 (3)0.012 (2)0.002 (2)
C40.050 (3)0.044 (3)0.044 (3)0.000 (3)0.005 (2)0.007 (3)
C50.042 (3)0.057 (3)0.049 (3)0.000 (3)0.018 (2)0.009 (3)
C60.050 (3)0.047 (3)0.043 (3)0.003 (3)0.017 (2)0.002 (3)
C70.058 (3)0.063 (4)0.043 (3)0.000 (3)0.013 (3)0.008 (3)
C80.100 (5)0.084 (5)0.039 (3)0.007 (4)0.030 (3)0.002 (3)
C90.147 (8)0.097 (6)0.067 (4)0.031 (6)0.061 (5)0.003 (4)
C210.054 (3)0.041 (3)0.032 (2)0.003 (3)0.019 (2)0.004 (2)
C220.054 (3)0.037 (3)0.049 (3)0.006 (2)0.023 (2)0.002 (2)
C230.061 (3)0.049 (3)0.044 (3)0.003 (3)0.016 (2)0.002 (3)
C240.051 (3)0.051 (3)0.047 (3)0.003 (3)0.017 (2)0.002 (3)
C250.061 (4)0.045 (3)0.054 (3)0.010 (3)0.026 (3)0.001 (3)
C260.056 (3)0.039 (3)0.046 (3)0.000 (3)0.019 (2)0.003 (2)
C510.040 (3)0.062 (4)0.047 (3)0.001 (3)0.006 (2)0.008 (3)
C520.052 (3)0.076 (4)0.061 (4)0.007 (3)0.020 (3)0.003 (3)
C530.062 (4)0.093 (6)0.081 (5)0.013 (4)0.018 (3)0.002 (4)
C540.063 (4)0.100 (6)0.085 (5)0.016 (4)0.013 (4)0.028 (5)
C550.091 (5)0.151 (9)0.064 (4)0.031 (6)0.025 (4)0.048 (5)
C560.073 (4)0.121 (7)0.055 (4)0.033 (5)0.027 (3)0.021 (4)
C610.041 (3)0.060 (4)0.041 (3)0.003 (3)0.015 (2)0.003 (3)
C620.061 (3)0.049 (3)0.052 (3)0.002 (3)0.022 (3)0.002 (3)
C630.075 (4)0.063 (4)0.063 (4)0.006 (3)0.031 (3)0.008 (3)
C640.067 (4)0.088 (5)0.039 (3)0.001 (4)0.021 (3)0.006 (3)
C650.074 (4)0.092 (5)0.043 (3)0.019 (4)0.011 (3)0.008 (3)
C660.056 (3)0.083 (5)0.049 (3)0.020 (3)0.014 (3)0.003 (3)
F10.0389 (17)0.081 (3)0.098 (3)0.0006 (17)0.0183 (16)0.008 (2)
F20.108 (3)0.138 (4)0.0422 (19)0.017 (3)0.0293 (19)0.012 (2)
N10.042 (2)0.069 (3)0.039 (2)0.000 (2)0.0158 (19)0.008 (2)
O10.091 (4)0.070 (3)0.097 (4)0.008 (3)0.026 (3)0.007 (3)
O20.095 (3)0.086 (4)0.052 (2)0.013 (3)0.025 (2)0.021 (2)
O30.075 (3)0.068 (3)0.0376 (19)0.009 (2)0.0207 (18)0.0008 (19)
S10.0503 (8)0.0671 (11)0.0578 (9)0.0094 (8)0.0181 (6)0.0134 (8)
Geometric parameters (Å, º) top
C2—N11.471 (6)C24—C251.366 (8)
C2—C211.506 (7)C25—C261.379 (8)
C2—C31.524 (7)C25—H250.9300
C2—H20.9800C26—H260.9300
C3—C41.355 (7)C51—C561.373 (8)
C3—C71.459 (7)C51—C521.397 (8)
C4—O11.371 (7)C51—S11.773 (6)
C4—C51.517 (7)C52—C531.374 (9)
C5—C61.528 (8)C52—H520.9300
C5—S11.835 (5)C53—C541.364 (9)
C5—H50.9800C53—H530.9300
C6—N11.471 (6)C54—C551.384 (10)
C6—C611.521 (7)C54—H540.9300
C6—H60.9800C55—C561.372 (10)
C7—O21.220 (7)C55—H560.9300
C7—O31.331 (7)C56—H360.9300
C8—O31.445 (6)C61—C621.376 (8)
C8—C91.516 (10)C61—C661.377 (8)
C8—H8A0.9700C62—C631.375 (8)
C8—H8B0.9700C62—H620.9300
C9—H9A0.9600C63—C641.343 (9)
C9—H9B0.9600C63—H630.9300
C9—H9C0.9600C64—F21.366 (6)
C21—C221.391 (7)C64—C651.376 (9)
C21—C261.396 (7)C65—C661.388 (8)
C22—C231.374 (7)C65—H650.9300
C22—H220.9300C66—H660.9300
C23—C241.372 (8)N1—H10.85 (6)
C23—H230.9300O1—H1A0.8200
C24—F11.356 (6)
N1—C2—C21106.1 (4)C25—C24—C23122.0 (5)
N1—C2—C3109.1 (4)C24—C25—C26118.8 (5)
C21—C2—C3112.3 (4)C24—C25—H25120.6
N1—C2—H2109.7C26—C25—H25120.6
C21—C2—H2109.7C25—C26—C21121.4 (5)
C3—C2—H2109.7C25—C26—H26119.3
C4—C3—C7120.2 (5)C21—C26—H26119.3
C4—C3—C2122.9 (4)C56—C51—C52117.9 (6)
C7—C3—C2117.0 (5)C56—C51—S1124.2 (5)
C3—C4—O1123.3 (5)C52—C51—S1117.7 (4)
C3—C4—C5121.4 (5)C53—C52—C51121.5 (6)
O1—C4—C5115.3 (5)C53—C52—H52119.3
C4—C5—C6111.3 (4)C51—C52—H52119.3
C4—C5—S1113.3 (4)C54—C53—C52119.5 (6)
C6—C5—S1111.9 (4)C54—C53—H53120.2
C4—C5—H5106.6C52—C53—H53120.2
C6—C5—H5106.6C53—C54—C55119.8 (7)
S1—C5—H5106.6C53—C54—H54120.1
N1—C6—C61107.7 (4)C55—C54—H54120.1
N1—C6—C5105.8 (4)C56—C55—C54120.5 (6)
C61—C6—C5113.3 (4)C56—C55—H56119.7
N1—C6—H6110.0C54—C55—H56119.7
C61—C6—H6110.0C55—C56—C51120.7 (6)
C5—C6—H6110.0C55—C56—H36119.6
O2—C7—O3121.8 (5)C51—C56—H36119.6
O2—C7—C3125.4 (6)C62—C61—C66118.4 (5)
O3—C7—C3112.9 (5)C62—C61—C6121.4 (5)
O3—C8—C9105.6 (5)C66—C61—C6120.1 (5)
O3—C8—H8A110.6C63—C62—C61121.2 (6)
C9—C8—H8A110.6C63—C62—H62119.4
O3—C8—H8B110.6C61—C62—H62119.4
C9—C8—H8B110.6C64—C63—C62119.0 (6)
H8A—C8—H8B108.8C64—C63—H63120.5
C8—C9—H9A109.5C62—C63—H63120.5
C8—C9—H9B109.5C63—C64—F2119.9 (6)
H9A—C9—H9B109.5C63—C64—C65122.8 (5)
C8—C9—H9C109.5F2—C64—C65117.4 (6)
H9A—C9—H9C109.5C64—C65—C66117.4 (6)
H9B—C9—H9C109.5C64—C65—H65121.3
C22—C21—C26117.3 (5)C66—C65—H65121.3
C22—C21—C2120.6 (4)C61—C66—C65121.3 (6)
C26—C21—C2122.0 (5)C61—C66—H66119.3
C23—C22—C21121.8 (5)C65—C66—H66119.3
C23—C22—H22119.1C6—N1—C2114.9 (4)
C21—C22—H22119.1C6—N1—H1107 (4)
C24—C23—C22118.6 (5)C2—N1—H1118 (4)
C24—C23—H23120.7C4—O1—H1A109.5
C22—C23—H23120.7C7—O3—C8116.4 (5)
F1—C24—C25119.2 (5)C51—S1—C5105.1 (3)
F1—C24—C23118.8 (5)
N1—C2—C3—C46.5 (7)C56—C51—C52—C531.0 (10)
C21—C2—C3—C4123.9 (5)S1—C51—C52—C53175.1 (5)
N1—C2—C3—C7175.1 (5)C51—C52—C53—C541.3 (11)
C21—C2—C3—C757.8 (6)C52—C53—C54—C550.1 (12)
C7—C3—C4—O110.9 (9)C53—C54—C55—C561.7 (14)
C2—C3—C4—O1170.8 (5)C54—C55—C56—C512.0 (13)
C7—C3—C4—C5171.0 (5)C52—C51—C56—C550.7 (11)
C2—C3—C4—C57.2 (8)S1—C51—C56—C55176.4 (6)
C3—C4—C5—C615.9 (7)N1—C6—C61—C62118.6 (6)
O1—C4—C5—C6165.8 (5)C5—C6—C61—C62124.8 (6)
C3—C4—C5—S1143.1 (5)N1—C6—C61—C6659.0 (7)
O1—C4—C5—S138.6 (6)C5—C6—C61—C6657.6 (7)
C4—C5—C6—N150.3 (6)C66—C61—C62—C630.9 (9)
S1—C5—C6—N1178.3 (3)C6—C61—C62—C63176.7 (5)
C4—C5—C6—C61168.1 (4)C61—C62—C63—C640.1 (9)
S1—C5—C6—C6164.0 (5)C62—C63—C64—F2179.3 (6)
C4—C3—C7—O215.2 (9)C62—C63—C64—C650.7 (10)
C2—C3—C7—O2166.5 (6)C63—C64—C65—C660.7 (10)
C4—C3—C7—O3164.7 (5)F2—C64—C65—C66179.3 (6)
C2—C3—C7—O313.7 (7)C62—C61—C66—C650.9 (9)
N1—C2—C21—C2257.4 (6)C6—C61—C66—C65176.8 (6)
C3—C2—C21—C2261.7 (6)C64—C65—C66—C610.1 (10)
N1—C2—C21—C26119.7 (5)C61—C6—N1—C2169.0 (5)
C3—C2—C21—C26121.2 (5)C5—C6—N1—C269.5 (6)
C26—C21—C22—C230.6 (7)C21—C2—N1—C6167.6 (5)
C2—C21—C22—C23176.6 (5)C3—C2—N1—C646.4 (6)
C21—C22—C23—C240.3 (8)O2—C7—O3—C81.4 (9)
C22—C23—C24—F1179.9 (5)C3—C7—O3—C8178.8 (5)
C22—C23—C24—C250.5 (8)C9—C8—O3—C7174.3 (6)
F1—C24—C25—C26179.6 (5)C56—C51—S1—C560.7 (6)
C23—C24—C25—C261.0 (8)C52—C51—S1—C5123.6 (5)
C24—C25—C26—C210.6 (8)C4—C5—S1—C5171.2 (5)
C22—C21—C26—C250.1 (7)C6—C5—S1—C5155.7 (4)
C2—C21—C26—C25177.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···F1i0.85 (6)2.46 (7)3.305 (7)179
C65—H65···O2ii0.932.373.252 (8)158
O1—H1A···S10.822.473.019 (5)125
C23—H23···Cg1iii0.932.893.504 (5)125
C53—H53···Cg2iv0.932.933.736 (8)146
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x, y+5/2, z1/2; (iii) x, y+1/2, z+1/2; (iv) x+1, y1/2, z+1/2.
 

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