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In the title compound, C26H22ClF2NO3S, a polysubstituted piperidine enol, the tetrahydropyridine ring adopts a half-chair conformation. The crystal structure is stabilized by van der Waals 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/S1600536807014316/ci2333sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014316/ci2333Isup2.hkl
Contains datablock I

CCDC reference: 647156

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.047
  • wR factor = 0.141
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for O1 - C4 .. 12.42 su
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C25 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C24 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1 ... ?
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 5 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 1 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: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

(2SR,5SR,6SR)-Ethyl 5-[(4-chlorophenyl)sulfanyl]-2,6-bis(4-fluorophenyl)- 4-hydroxy-1,2,5,6-tetrahydropyridine-3-carboxylate top
Crystal data top
C26H22ClF2NO3SF(000) = 1040
Mr = 501.96Dx = 1.363 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 10.1341 (9) Åθ = 2–25°
b = 13.8290 (13) ŵ = 0.29 mm1
c = 17.9627 (15) ÅT = 293 K
β = 103.729 (17)°Block, colourless
V = 2445.4 (4) Å30.20 × 0.16 × 0.11 mm
Z = 4
Data collection top
Nonius MACH-3 four-circle
diffractometer
2252 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 25.0°, θmin = 2.1°
ω scansh = 012
Absorption correction: ψ scan
(North et al., 1968)
k = 116
Tmin = 0.945, Tmax = 0.969l = 2120
4955 measured reflections3 standard reflections every 60 min
4290 independent reflections intensity decay: none
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0586P)2 + 1.1086P]
where P = (Fo2 + 2Fc2)/3
4290 reflections(Δ/σ)max = 0.001
313 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = 0.41 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
C21.0251 (3)0.1400 (2)0.11212 (18)0.0424 (8)
H21.05560.14120.06430.051*
C30.9756 (3)0.0385 (2)0.12021 (18)0.0387 (8)
C40.8524 (3)0.0215 (2)0.13535 (18)0.0401 (8)
C50.7623 (3)0.1019 (2)0.15266 (18)0.0427 (8)
H50.68660.10690.10730.051*
C60.8318 (3)0.2009 (2)0.16127 (18)0.0413 (8)
H60.89510.20490.21180.050*
C71.0577 (3)0.0405 (3)0.10502 (18)0.0440 (9)
C81.2692 (3)0.0824 (3)0.0770 (2)0.0540 (9)
H8A1.22660.11890.03150.065*
H8B1.29460.12680.11980.065*
C91.3914 (4)0.0305 (3)0.0649 (2)0.0756 (13)
H9A1.36510.01280.02210.113*
H9B1.45570.07660.05460.113*
H9C1.43220.00570.11010.113*
C211.1463 (3)0.1717 (2)0.1753 (2)0.0422 (8)
C221.1578 (3)0.1509 (3)0.2518 (2)0.0541 (10)
H221.09100.11370.26560.065*
C231.2661 (4)0.1841 (3)0.3085 (2)0.0650 (11)
H231.27170.17040.35990.078*
C241.3637 (4)0.2371 (3)0.2871 (3)0.0755 (13)
C251.3590 (5)0.2577 (4)0.2131 (4)0.0944 (16)
H251.42770.29360.20000.113*
C261.2494 (4)0.2244 (3)0.1567 (3)0.0741 (13)
H261.24560.23800.10550.089*
C510.8297 (3)0.0694 (3)0.31204 (18)0.0441 (8)
C520.8535 (4)0.1454 (3)0.3633 (2)0.0600 (11)
H520.79270.19680.35750.072*
C530.9689 (5)0.1449 (3)0.4236 (2)0.0694 (12)
H530.98530.19620.45810.083*
C541.0573 (4)0.0701 (3)0.4323 (2)0.0588 (10)
C551.0345 (4)0.0067 (3)0.3829 (2)0.0574 (10)
H551.09560.05790.38940.069*
C560.9194 (4)0.0073 (3)0.3231 (2)0.0502 (9)
H560.90230.06000.29000.060*
C610.7350 (3)0.2847 (2)0.15161 (18)0.0422 (8)
C620.6456 (4)0.3037 (3)0.0810 (2)0.0584 (10)
H620.64300.26170.04030.070*
C630.5614 (4)0.3831 (3)0.0705 (2)0.0635 (11)
H630.50250.39520.02320.076*
C640.5664 (4)0.4435 (3)0.1310 (2)0.0565 (10)
C650.6522 (4)0.4290 (3)0.2012 (2)0.0542 (9)
H650.65380.47160.24150.065*
C660.7366 (3)0.3489 (3)0.21068 (19)0.0479 (9)
H660.79590.33810.25800.057*
Cl11.20456 (12)0.07175 (11)0.50535 (6)0.0929 (4)
F11.4714 (3)0.2682 (2)0.34295 (18)0.1227 (11)
F20.4836 (3)0.52266 (18)0.12075 (14)0.0847 (8)
N10.9090 (3)0.2072 (2)0.10121 (16)0.0471 (8)
O10.7976 (3)0.0701 (2)0.13362 (18)0.0826 (9)
H1A0.73660.06990.15660.124*
O21.0304 (2)0.12664 (19)0.10421 (14)0.0589 (7)
O31.1775 (2)0.01028 (17)0.09261 (13)0.0528 (6)
S10.68451 (9)0.07411 (8)0.23310 (5)0.0549 (3)
H10.941 (3)0.265 (3)0.1011 (19)0.051 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0457 (19)0.043 (2)0.0428 (19)0.0052 (17)0.0186 (16)0.0095 (16)
C30.0414 (18)0.037 (2)0.0365 (18)0.0013 (16)0.0074 (14)0.0023 (15)
C40.0426 (19)0.039 (2)0.0364 (18)0.0082 (17)0.0055 (14)0.0011 (16)
C50.0397 (18)0.052 (2)0.0354 (18)0.0022 (17)0.0063 (14)0.0050 (16)
C60.0394 (18)0.049 (2)0.0360 (18)0.0030 (16)0.0099 (14)0.0050 (16)
C70.047 (2)0.048 (2)0.0347 (18)0.0002 (18)0.0043 (15)0.0014 (16)
C80.050 (2)0.060 (3)0.053 (2)0.011 (2)0.0155 (17)0.003 (2)
C90.056 (2)0.097 (4)0.077 (3)0.009 (2)0.023 (2)0.006 (3)
C210.0382 (18)0.033 (2)0.058 (2)0.0021 (16)0.0175 (16)0.0029 (17)
C220.043 (2)0.057 (3)0.060 (2)0.0100 (18)0.0070 (18)0.005 (2)
C230.051 (2)0.073 (3)0.068 (3)0.005 (2)0.008 (2)0.008 (2)
C240.049 (2)0.073 (3)0.100 (4)0.021 (2)0.010 (2)0.028 (3)
C250.072 (3)0.091 (4)0.124 (4)0.047 (3)0.031 (3)0.006 (3)
C260.071 (3)0.074 (3)0.083 (3)0.026 (3)0.031 (2)0.008 (3)
C510.049 (2)0.043 (2)0.044 (2)0.0023 (18)0.0194 (16)0.0075 (18)
C520.093 (3)0.041 (2)0.048 (2)0.012 (2)0.021 (2)0.0030 (19)
C530.116 (4)0.048 (3)0.042 (2)0.011 (3)0.015 (2)0.001 (2)
C540.073 (3)0.060 (3)0.042 (2)0.010 (2)0.0121 (19)0.009 (2)
C550.062 (2)0.062 (3)0.050 (2)0.009 (2)0.0176 (19)0.010 (2)
C560.061 (2)0.045 (2)0.046 (2)0.002 (2)0.0164 (18)0.0007 (18)
C610.0397 (18)0.047 (2)0.0407 (19)0.0034 (17)0.0117 (15)0.0029 (17)
C620.060 (2)0.064 (3)0.045 (2)0.015 (2)0.0005 (18)0.008 (2)
C630.061 (2)0.069 (3)0.052 (2)0.018 (2)0.0014 (19)0.003 (2)
C640.050 (2)0.051 (3)0.068 (3)0.011 (2)0.0127 (19)0.004 (2)
C650.061 (2)0.052 (2)0.054 (2)0.001 (2)0.0220 (19)0.007 (2)
C660.048 (2)0.052 (2)0.043 (2)0.0010 (19)0.0106 (16)0.0030 (18)
Cl10.0785 (8)0.1332 (12)0.0581 (6)0.0254 (8)0.0014 (5)0.0084 (8)
F10.0786 (18)0.134 (3)0.142 (3)0.0496 (18)0.0011 (18)0.047 (2)
F20.0831 (16)0.0715 (18)0.0953 (18)0.0330 (15)0.0127 (14)0.0008 (14)
N10.0524 (18)0.044 (2)0.0484 (17)0.0053 (17)0.0198 (14)0.0128 (15)
O10.081 (2)0.084 (2)0.083 (2)0.0206 (18)0.0217 (16)0.0047 (18)
O20.0642 (16)0.0428 (17)0.0709 (18)0.0019 (14)0.0186 (13)0.0030 (14)
O30.0496 (14)0.0503 (16)0.0624 (16)0.0027 (12)0.0211 (12)0.0040 (13)
S10.0415 (5)0.0724 (7)0.0537 (5)0.0013 (5)0.0171 (4)0.0089 (5)
Geometric parameters (Å, º) top
C2—N11.474 (4)C24—F11.365 (5)
C2—C31.509 (5)C25—C261.393 (6)
C2—C211.526 (4)C25—H250.93
C2—H20.98C26—H260.93
C3—C41.360 (4)C51—C561.379 (5)
C3—C71.439 (5)C51—C521.381 (5)
C4—O11.381 (4)C51—S11.786 (3)
C4—C51.518 (5)C52—C531.393 (5)
C5—C61.530 (5)C52—H520.93
C5—S11.843 (3)C53—C541.353 (6)
C5—H50.98C53—H530.93
C6—N11.478 (4)C54—C551.368 (5)
C6—C611.502 (4)C54—Cl11.738 (4)
C6—H60.98C55—C561.386 (5)
C7—O21.222 (4)C55—H550.93
C7—O31.352 (4)C56—H560.93
C8—O31.436 (4)C61—C661.380 (4)
C8—C91.491 (5)C61—C621.397 (4)
C8—H8A0.97C62—C631.376 (5)
C8—H8B0.97C62—H620.93
C9—H9A0.96C63—C641.362 (5)
C9—H9B0.96C63—H630.93
C9—H9C0.96C64—F21.365 (4)
C21—C261.379 (5)C64—C651.367 (5)
C21—C221.381 (5)C65—C661.385 (5)
C22—C231.386 (5)C65—H650.93
C22—H220.93C66—H660.93
C23—C241.358 (6)N1—H10.86 (3)
C23—H230.93O1—H1A0.82
C24—C251.349 (6)
N1—C2—C3109.0 (3)C23—C24—F1118.2 (5)
N1—C2—C21113.3 (3)C24—C25—C26118.9 (4)
C3—C2—C21115.0 (3)C24—C25—H25120.6
N1—C2—H2106.3C26—C25—H25120.6
C3—C2—H2106.3C21—C26—C25121.2 (4)
C21—C2—H2106.3C21—C26—H26119.4
C4—C3—C7120.4 (3)C25—C26—H26119.4
C4—C3—C2121.5 (3)C56—C51—C52119.0 (3)
C7—C3—C2117.9 (3)C56—C51—S1122.2 (3)
C3—C4—O1122.6 (3)C52—C51—S1118.8 (3)
C3—C4—C5122.7 (3)C51—C52—C53119.8 (4)
O1—C4—C5114.7 (3)C51—C52—H52120.1
C4—C5—C6113.0 (3)C53—C52—H52120.1
C4—C5—S1113.4 (2)C54—C53—C52120.3 (4)
C6—C5—S1112.3 (2)C54—C53—H53119.9
C4—C5—H5105.7C52—C53—H53119.9
C6—C5—H5105.7C53—C54—C55120.9 (4)
S1—C5—H5105.7C53—C54—Cl1120.2 (3)
N1—C6—C61108.4 (3)C55—C54—Cl1118.9 (3)
N1—C6—C5106.8 (3)C54—C55—C56119.3 (4)
C61—C6—C5113.9 (3)C54—C55—H55120.4
N1—C6—H6109.2C56—C55—H55120.4
C61—C6—H6109.2C51—C56—C55120.8 (4)
C5—C6—H6109.2C51—C56—H56119.6
O2—C7—O3120.6 (3)C55—C56—H56119.6
O2—C7—C3127.1 (3)C66—C61—C62117.6 (3)
O3—C7—C3112.2 (3)C66—C61—C6121.3 (3)
O3—C8—C9107.0 (3)C62—C61—C6121.0 (3)
O3—C8—H8A110.3C63—C62—C61121.5 (4)
C9—C8—H8A110.3C63—C62—H62119.3
O3—C8—H8B110.3C61—C62—H62119.3
C9—C8—H8B110.3C64—C63—C62118.3 (4)
H8A—C8—H8B108.6C64—C63—H63120.8
C8—C9—H9A109.5C62—C63—H63120.8
C8—C9—H9B109.5C63—C64—F2118.6 (3)
H9A—C9—H9B109.5C63—C64—C65122.8 (4)
C8—C9—H9C109.5F2—C64—C65118.5 (4)
H9A—C9—H9C109.5C64—C65—C66118.0 (3)
H9B—C9—H9C109.5C64—C65—H65121.0
C26—C21—C22117.5 (3)C66—C65—H65121.0
C26—C21—C2119.6 (3)C61—C66—C65121.7 (3)
C22—C21—C2122.9 (3)C61—C66—H66119.1
C21—C22—C23121.9 (3)C65—C66—H66119.1
C21—C22—H22119.1C2—N1—C6114.2 (3)
C23—C22—H22119.1C2—N1—H1107 (2)
C24—C23—C22118.2 (4)C6—N1—H1109 (2)
C24—C23—H23120.9C4—O1—H1A109.5
C22—C23—H23120.9C7—O3—C8117.8 (3)
C25—C24—C23122.3 (4)C51—S1—C5101.83 (14)
C25—C24—F1119.5 (4)
N1—C2—C3—C415.9 (4)S1—C51—C52—C53177.6 (3)
C21—C2—C3—C4112.5 (3)C51—C52—C53—C540.2 (6)
N1—C2—C3—C7159.0 (3)C52—C53—C54—C550.8 (6)
C21—C2—C3—C772.7 (4)C52—C53—C54—Cl1177.5 (3)
C7—C3—C4—O13.0 (5)C53—C54—C55—C560.3 (6)
C2—C3—C4—O1171.7 (3)Cl1—C54—C55—C56178.1 (3)
C7—C3—C4—C5179.3 (3)C52—C51—C56—C552.4 (5)
C2—C3—C4—C56.0 (5)S1—C51—C56—C55177.0 (3)
C3—C4—C5—C67.4 (4)C54—C55—C56—C511.4 (5)
O1—C4—C5—C6174.8 (3)N1—C6—C61—C66123.6 (3)
C3—C4—C5—S1136.7 (3)C5—C6—C61—C66117.7 (3)
O1—C4—C5—S145.4 (3)N1—C6—C61—C6252.6 (4)
C4—C5—C6—N140.7 (3)C5—C6—C61—C6266.2 (4)
S1—C5—C6—N1170.6 (2)C66—C61—C62—C630.4 (5)
C4—C5—C6—C61160.3 (3)C6—C61—C62—C63176.6 (3)
S1—C5—C6—C6169.8 (3)C61—C62—C63—C640.2 (6)
C4—C3—C7—O20.4 (5)C62—C63—C64—F2179.7 (3)
C2—C3—C7—O2175.3 (3)C62—C63—C64—C650.6 (6)
C4—C3—C7—O3178.9 (3)C63—C64—C65—C660.4 (6)
C2—C3—C7—O36.2 (4)F2—C64—C65—C66179.4 (3)
N1—C2—C21—C2694.7 (4)C62—C61—C66—C650.6 (5)
C3—C2—C21—C26139.0 (3)C6—C61—C66—C65176.9 (3)
N1—C2—C21—C2284.4 (4)C64—C65—C66—C610.3 (5)
C3—C2—C21—C2241.8 (4)C3—C2—N1—C654.3 (4)
C26—C21—C22—C232.0 (6)C21—C2—N1—C675.1 (4)
C2—C21—C22—C23177.1 (3)C61—C6—N1—C2169.3 (3)
C21—C22—C23—C241.0 (6)C5—C6—N1—C267.5 (3)
C22—C23—C24—C250.4 (7)O2—C7—O3—C81.3 (5)
C22—C23—C24—F1178.9 (4)C3—C7—O3—C8179.8 (3)
C23—C24—C25—C260.7 (8)C9—C8—O3—C7179.5 (3)
F1—C24—C25—C26179.2 (4)C56—C51—S1—C574.2 (3)
C22—C21—C26—C251.7 (6)C52—C51—S1—C5105.2 (3)
C2—C21—C26—C25177.5 (4)C4—C5—S1—C5165.8 (3)
C24—C25—C26—C210.4 (7)C6—C5—S1—C5163.9 (3)
C56—C51—C52—C531.8 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···S10.822.553.075 (3)123
C22—H22···Cg10.932.773.598 (4)149
C25—H25···Cg2i0.932.883.792 (5)167
C55—H55···Cg2ii0.932.963.771 (4)146
Symmetry codes: (i) x+1, y, z; (ii) x+2, y1/2, z+1/2.
 

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