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In the title compound, C17H21NO3, the cyclo­hexene ring adopts an envelope conformation. The phenyl ring forms a dihedral angle of 35.77 (4)° with the amide plane. In the crystal, the symmetry-related mol­ecules are linked through N—H...O, O—H...O and weak C—H...O hydrogen bonds, to form molecular networks parallel to (110).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803001442/ci6196sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803001442/ci6196Isup2.hkl
Contains datablock I

CCDC reference: 206750

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.045
  • wR factor = 0.127
  • Data-to-parameter ratio = 20.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

5,5'-dimethyl-2-(4-methylphenylaminocarbomethyl)-1,3-cyclohexanedione top
Crystal data top
C17H21NO3F(000) = 616
Mr = 287.35Dx = 1.210 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5446 reflections
a = 10.1239 (1) Åθ = 2.0–28.2°
b = 5.8366 (1) ŵ = 0.08 mm1
c = 26.9176 (1) ÅT = 293 K
β = 97.403 (1)°Block, colourless
V = 1577.28 (3) Å30.48 × 0.34 × 0.26 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer
2972 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
Graphite monochromatorθmax = 28.3°, θmin = 1.5°
ω scansh = 1313
10433 measured reflectionsk = 67
3912 independent reflectionsl = 3530
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0589P)2 + 0.2846P]
where P = (Fo2 + 2Fc2)/3
3912 reflections(Δ/σ)max < 0.001
191 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.29 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*/UeqOcc. (<1)
O10.42145 (10)0.7722 (2)0.18838 (4)0.0646 (4)
O20.64846 (11)0.8907 (2)0.29964 (5)0.0702 (4)
O30.30067 (9)0.36982 (18)0.27417 (4)0.0464 (3)
H3O0.22920.34580.28450.070*
N10.62787 (10)0.6838 (2)0.17272 (4)0.0423 (3)
H1N0.69770.60340.18230.051*
C10.63017 (12)0.8209 (2)0.12927 (5)0.0403 (3)
C20.69852 (14)0.7394 (3)0.09149 (5)0.0472 (3)
H20.73860.59580.09450.057*
C30.70730 (15)0.8712 (3)0.04929 (6)0.0544 (4)
H30.75440.81500.02440.065*
C40.64782 (15)1.0843 (3)0.04320 (6)0.0533 (4)
C50.57921 (16)1.1616 (3)0.08113 (7)0.0581 (4)
H50.53741.30360.07770.070*
C60.57085 (15)1.0342 (3)0.12397 (6)0.0523 (4)
H60.52541.09210.14910.063*
C70.6594 (2)1.2274 (4)0.00282 (7)0.0763 (6)
H7A0.62451.14310.03220.114*0.50
H7B0.75131.26350.00430.114*0.50
H7C0.60961.36660.00120.114*0.50
H7D0.69911.37240.00710.114*0.50
H7E0.57231.25200.02080.114*0.50
H7F0.71401.14880.02400.114*0.50
C80.52657 (12)0.6685 (2)0.20012 (5)0.0397 (3)
C90.54615 (12)0.5127 (2)0.24532 (5)0.0394 (3)
H9A0.50710.36410.23660.047*
H9B0.64060.49120.25590.047*
C100.48195 (11)0.6146 (2)0.28767 (5)0.0345 (3)
C110.54351 (13)0.8149 (3)0.31184 (5)0.0444 (3)
C120.47275 (16)0.9387 (3)0.34964 (6)0.0552 (4)
H12A0.41561.05490.33240.066*
H12B0.53851.01620.37320.066*
C130.38838 (13)0.7842 (2)0.37889 (5)0.0434 (3)
C140.29616 (12)0.6464 (2)0.34088 (5)0.0395 (3)
H14A0.25540.52540.35840.047*
H14B0.22540.74600.32580.047*
C150.36369 (11)0.5415 (2)0.30016 (4)0.0337 (3)
C160.30472 (19)0.9308 (3)0.41020 (7)0.0667 (5)
H16A0.25190.83300.42850.100*
H16B0.24721.02910.38850.100*
H16C0.36261.02250.43330.100*
C170.47746 (19)0.6245 (4)0.41353 (6)0.0714 (5)
H17A0.53010.53230.39400.107*
H17B0.42310.52700.43120.107*
H17C0.53520.71400.43710.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0364 (5)0.0968 (9)0.0649 (7)0.0286 (5)0.0228 (5)0.0312 (6)
O20.0518 (6)0.0775 (8)0.0862 (8)0.0345 (6)0.0277 (6)0.0169 (7)
O30.0357 (5)0.0542 (6)0.0518 (6)0.0147 (4)0.0157 (4)0.0157 (5)
N10.0317 (5)0.0515 (7)0.0464 (6)0.0109 (5)0.0159 (4)0.0092 (5)
C10.0327 (6)0.0473 (7)0.0426 (7)0.0011 (5)0.0119 (5)0.0044 (6)
C20.0420 (7)0.0531 (8)0.0493 (8)0.0047 (6)0.0166 (6)0.0012 (6)
C30.0525 (8)0.0697 (10)0.0444 (8)0.0083 (8)0.0191 (6)0.0015 (7)
C40.0482 (8)0.0618 (10)0.0499 (8)0.0147 (7)0.0064 (6)0.0101 (7)
C50.0571 (9)0.0481 (9)0.0709 (10)0.0011 (7)0.0158 (8)0.0127 (8)
C60.0545 (8)0.0487 (8)0.0578 (9)0.0059 (7)0.0232 (7)0.0044 (7)
C70.0820 (13)0.0866 (14)0.0600 (10)0.0224 (11)0.0086 (9)0.0231 (10)
C80.0290 (6)0.0502 (8)0.0417 (7)0.0064 (5)0.0114 (5)0.0026 (6)
C90.0299 (6)0.0449 (7)0.0455 (7)0.0040 (5)0.0130 (5)0.0032 (6)
C100.0282 (5)0.0381 (6)0.0385 (6)0.0010 (5)0.0088 (4)0.0018 (5)
C110.0365 (6)0.0461 (8)0.0519 (8)0.0101 (6)0.0102 (5)0.0002 (6)
C120.0535 (8)0.0467 (8)0.0680 (10)0.0137 (7)0.0174 (7)0.0150 (7)
C130.0420 (7)0.0478 (8)0.0414 (7)0.0033 (6)0.0086 (5)0.0077 (6)
C140.0323 (6)0.0484 (7)0.0396 (6)0.0041 (5)0.0117 (5)0.0037 (6)
C150.0295 (5)0.0372 (6)0.0349 (6)0.0020 (5)0.0059 (4)0.0008 (5)
C160.0702 (11)0.0729 (11)0.0608 (10)0.0030 (9)0.0230 (8)0.0235 (9)
C170.0717 (11)0.0903 (14)0.0487 (9)0.0107 (10)0.0062 (8)0.0001 (9)
Geometric parameters (Å, º) top
O1—C81.229 (2)C7—H7F0.96
O2—C111.234 (2)C8—C91.511 (2)
O3—C151.336 (2)C9—C101.506 (2)
O3—H3O0.82C9—H9A0.97
N1—C81.341 (2)C9—H9B0.97
N1—C11.420 (2)C10—C151.354 (2)
N1—H1N0.86C10—C111.440 (2)
C1—C61.381 (2)C11—C121.503 (2)
C1—C21.3859 (18)C12—C131.528 (2)
C2—C31.384 (2)C12—H12A0.97
C2—H20.93C12—H12B0.97
C3—C41.382 (2)C13—C141.523 (2)
C3—H30.93C13—C171.528 (2)
C4—C51.382 (2)C13—C161.531 (2)
C4—C71.511 (2)C14—C151.496 (2)
C5—C61.384 (2)C14—H14A0.97
C5—H50.93C14—H14B0.97
C6—H60.93C16—H16A0.96
C7—H7A0.96C16—H16B0.96
C7—H7B0.96C16—H16C0.96
C7—H7C0.96C17—H17A0.96
C7—H7D0.96C17—H17B0.96
C7—H7E0.96C17—H17C0.96
C15—O3—H3O109.5C10—C9—C8110.33 (10)
C8—N1—C1125.8 (1)C10—C9—H9A109.6
C8—N1—H1N117.1C8—C9—H9A109.6
C1—N1—H1N117.1C10—C9—H9B109.6
C6—C1—C2119.03 (13)C8—C9—H9B109.6
C6—C1—N1122.67 (12)H9A—C9—H9B108.1
C2—C1—N1118.27 (12)C15—C10—C11119.28 (11)
C3—C2—C1120.15 (14)C15—C10—C9123.05 (11)
C3—C2—H2119.9C11—C10—C9117.30 (11)
C1—C2—H2119.9O2—C11—C10120.5 (1)
C4—C3—C2121.61 (14)O2—C11—C12120.7 (1)
C4—C3—H3119.2C10—C11—C12118.7 (1)
C2—C3—H3119.2C11—C12—C13114.34 (12)
C3—C4—C5117.30 (14)C11—C12—H12A108.7
C3—C4—C7121.07 (16)C13—C12—H12A108.7
C5—C4—C7121.62 (17)C11—C12—H12B108.7
C4—C5—C6122.05 (15)C13—C12—H12B108.7
C4—C5—H5119.0H12A—C12—H12B107.6
C6—C5—H5119.0C14—C13—C17110.53 (13)
C1—C6—C5119.83 (14)C14—C13—C12107.48 (11)
C1—C6—H6120.1C17—C13—C12110.43 (14)
C5—C6—H6120.1C14—C13—C16109.29 (12)
C4—C7—H7A109.5C17—C13—C16109.27 (13)
C4—C7—H7B109.5C12—C13—C16109.83 (13)
H7A—C7—H7B109.5C15—C14—C13114.21 (10)
C4—C7—H7C109.5C15—C14—H14A108.7
H7A—C7—H7C109.5C13—C14—H14A108.7
H7B—C7—H7C109.5C15—C14—H14B108.7
C4—C7—H7D109.5C13—C14—H14B108.7
H7A—C7—H7D141.1H14A—C14—H14B107.6
H7B—C7—H7D56.3O3—C15—C10119.0 (1)
H7C—C7—H7D56.3O3—C15—C14117.3 (1)
C4—C7—H7E109.5C10—C15—C14123.7 (1)
H7A—C7—H7E56.3C13—C16—H16A109.5
H7B—C7—H7E141.1C13—C16—H16B109.5
H7C—C7—H7E56.3H16A—C16—H16B109.5
H7D—C7—H7E109.5C13—C16—H16C109.5
C4—C7—H7F109.5H16A—C16—H16C109.5
H7A—C7—H7F56.3H16B—C16—H16C109.5
H7B—C7—H7F56.3C13—C17—H17A109.5
H7C—C7—H7F141.1C13—C17—H17B109.5
H7D—C7—H7F109.5H17A—C17—H17B109.5
H7E—C7—H7F109.5C13—C17—H17C109.5
O1—C8—N1121.58 (12)H17A—C17—H17C109.5
O1—C8—C9121.49 (11)H17B—C17—H17C109.5
N1—C8—C9116.91 (11)
C8—N1—C1—C636.0 (2)C15—C10—C11—O2176.95 (14)
C8—N1—C1—C2146.13 (15)C9—C10—C11—O23.7 (2)
C6—C1—C2—C30.3 (2)C15—C10—C11—C121.0 (2)
N1—C1—C2—C3177.69 (13)C9—C10—C11—C12172.24 (12)
C1—C2—C3—C40.8 (2)O2—C11—C12—C13152.64 (15)
C2—C3—C4—C50.2 (2)C10—C11—C12—C1331.5 (2)
C2—C3—C4—C7179.4 (2)C11—C12—C13—C1452.58 (17)
C3—C4—C5—C60.8 (2)C11—C12—C13—C1768.05 (17)
C7—C4—C5—C6178.4 (2)C11—C12—C13—C16171.38 (13)
C2—C1—C6—C50.7 (2)C17—C13—C14—C1573.97 (16)
N1—C1—C6—C5178.56 (14)C12—C13—C14—C1546.60 (16)
C4—C5—C6—C11.2 (3)C16—C13—C14—C15165.74 (13)
C1—N1—C8—O12.1 (2)C11—C10—C15—O3173.40 (12)
C1—N1—C8—C9179.52 (12)C9—C10—C15—O30.52 (19)
O1—C8—C9—C1038.60 (18)C11—C10—C15—C144.8 (2)
N1—C8—C9—C10143.1 (1)C9—C10—C15—C14177.68 (11)
C8—C9—C10—C15102.62 (14)C13—C14—C15—O3161.75 (12)
C8—C9—C10—C1170.39 (15)C13—C14—C15—C1020.02 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O10.932.452.8824 (18)109
C9—H9A···O30.972.442.8235 (15)103
O3—H3O···O1i0.821.822.6423 (12)174
C14—H14A···O1i0.972.533.1301 (17)120
N1—H1N···O2ii0.862.002.8591 (15)174
Symmetry codes: (i) x+1/2, y1/2, z+1/2; (ii) x+3/2, y1/2, z+1/2.
 

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