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In the title compound, C15H22O2, the C=C bond lengths in the cyclo­hexene ring and the allylic acid group [1.325 (3) and 1.324 (3) Å] are almost equal and are shorter than those observed in ethyl­ene. The C=O and C—O bond lengths in the allylic acid group [1.201 (3) and 1.321 (3) Å] are almost equal to those of formic acid. There is an intra­molecular hydrogen bond between the allylic acid H atom and the hydr­oxy O atom [C...O = 2.673 (2) Å and C—H...O = 101°].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806012566/er6042sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806012566/er6042Isup2.hkl
Contains datablock I

CCDC reference: 608324

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.047
  • wR factor = 0.126
  • Data-to-parameter ratio = 11.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT126_ALERT_1_C Error in or Uninterpretable Hall Symbol ....... P AC AB PLAT127_ALERT_1_C Implicit Hall Symbol Inconsistent with Explicit P ac ab PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged .... H10 PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged .... H2
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.99 From the CIF: _reflns_number_total 1865 Count of symmetry unique reflns 1880 Completeness (_total/calc) 99.20% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.

Pterodontic acid top
Crystal data top
C15H22O2F(000) = 512
Mr = 234.33Dx = 1.158 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P ac abCell parameters from 4272 reflections
a = 6.3425 (7) Åθ = 2.7–26.6°
b = 14.0242 (15) ŵ = 0.08 mm1
c = 15.1156 (16) ÅT = 292 K
V = 1344.5 (3) Å3Block, colorless
Z = 40.30 × 0.20 × 0.20 mm
Data collection top
Bruekr SMART CCD area-detector
diffractometer
1865 independent reflections
Radiation source: fine-focus sealed tube1676 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 10 pixels mm-1θmax = 28.0°, θmin = 2.0°
φ and ω scansh = 88
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
k = 1816
Tmin = 0.978, Tmax = 0.985l = 1919
10414 measured 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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0813P)2 + 0.0392P]
where P = (Fo2 + 2Fc2)/3
1865 reflections(Δ/σ)max < 0.001
165 parametersΔρmax = 0.24 e Å3
1 restraintΔρmin = 0.18 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 &gt; 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
O10.2674 (3)0.77996 (13)0.94391 (9)0.0639 (5)
O20.5976 (3)0.76509 (15)0.89728 (9)0.0671 (5)
C150.3940 (3)0.77953 (13)0.88478 (12)0.0429 (4)
C100.1200 (3)0.83565 (14)0.77384 (11)0.0408 (4)
H100.020 (4)0.8000 (17)0.8104 (14)0.049*
C60.0907 (3)0.99114 (13)0.66582 (12)0.0417 (4)
C90.0512 (3)0.82603 (13)0.67860 (12)0.0419 (4)
H90.07300.76710.65200.050*
C80.0371 (3)0.89307 (13)0.62917 (11)0.0385 (4)
C110.1111 (4)0.94016 (15)0.80279 (12)0.0501 (5)
H11A0.11280.94380.86690.060*
H11B0.23400.97370.78060.060*
C130.3367 (3)0.79472 (13)0.79024 (11)0.0395 (4)
C20.0944 (4)0.87123 (16)0.53294 (12)0.0485 (5)
H20.097 (4)0.802 (2)0.5270 (15)0.058*
C50.3155 (4)1.01941 (17)0.63687 (14)0.0543 (5)
H5A0.41640.98000.66830.065*
H5B0.34101.08520.65360.065*
C40.3520 (4)1.00876 (18)0.53798 (15)0.0604 (6)
H4A0.49501.02780.52360.072*
H4B0.25601.05020.50600.072*
C140.4752 (4)0.77196 (17)0.72817 (12)0.0561 (6)
H14A0.60570.74700.74390.067*
H14B0.44190.78100.66880.067*
C120.0879 (4)0.98722 (16)0.76764 (13)0.0526 (5)
H12A0.09761.05150.79100.063*
H12B0.21000.95190.78820.063*
C30.3170 (4)0.90683 (18)0.50996 (14)0.0570 (6)
H3A0.33860.90160.44660.068*
H3B0.42020.86640.53890.068*
C70.0681 (4)1.06739 (15)0.63492 (16)0.0570 (6)
H7A0.20871.04680.64860.085*
H7B0.03961.12650.66470.085*
H7C0.05491.07640.57220.085*
C10.0698 (5)0.9083 (2)0.46701 (14)0.0691 (7)
H1A0.06770.97680.46670.104*
H1B0.03720.88510.40890.104*
H1C0.20730.88640.48410.104*
H2A0.622 (6)0.751 (3)0.9489 (10)0.104*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0695 (11)0.0883 (12)0.0340 (6)0.0019 (9)0.0052 (7)0.0140 (7)
O20.0609 (10)0.0990 (13)0.0416 (7)0.0134 (10)0.0121 (7)0.0128 (8)
C150.0520 (11)0.0431 (10)0.0338 (8)0.0016 (9)0.0041 (8)0.0059 (7)
C100.0444 (10)0.0447 (9)0.0332 (8)0.0019 (8)0.0015 (8)0.0054 (7)
C60.0430 (10)0.0395 (9)0.0425 (9)0.0010 (8)0.0016 (8)0.0014 (7)
C90.0512 (11)0.0359 (8)0.0384 (8)0.0003 (8)0.0072 (8)0.0038 (7)
C80.0395 (9)0.0422 (9)0.0340 (8)0.0030 (8)0.0037 (7)0.0002 (7)
C110.0585 (13)0.0538 (11)0.0381 (9)0.0042 (10)0.0078 (9)0.0098 (8)
C130.0472 (10)0.0385 (8)0.0330 (8)0.0047 (8)0.0010 (7)0.0065 (7)
C20.0579 (12)0.0507 (11)0.0369 (9)0.0035 (10)0.0109 (9)0.0015 (8)
C50.0502 (12)0.0556 (12)0.0573 (12)0.0095 (10)0.0013 (10)0.0070 (10)
C40.0484 (13)0.0757 (15)0.0571 (12)0.0052 (11)0.0108 (10)0.0169 (11)
C140.0576 (13)0.0756 (15)0.0353 (9)0.0066 (12)0.0018 (9)0.0074 (9)
C120.0596 (13)0.0564 (11)0.0417 (9)0.0142 (11)0.0010 (9)0.0108 (8)
C30.0558 (13)0.0737 (14)0.0416 (10)0.0130 (12)0.0144 (10)0.0079 (10)
C70.0574 (14)0.0452 (11)0.0683 (13)0.0081 (10)0.0012 (12)0.0005 (10)
C10.0659 (16)0.1010 (19)0.0405 (10)0.0000 (15)0.0023 (11)0.0053 (12)
Geometric parameters (Å, º) top
O1—C151.201 (3)C2—C31.538 (3)
O2—C151.321 (3)C2—H20.98 (3)
O2—H2A0.820 (10)C5—C41.520 (3)
C15—C131.490 (2)C5—H5A0.9700
C10—C131.510 (3)C5—H5B0.9700
C10—C91.510 (2)C4—C31.507 (4)
C10—C111.531 (3)C4—H4A0.9700
C10—H100.98 (2)C4—H4B0.9700
C6—C81.521 (3)C14—H14A0.9300
C6—C121.540 (3)C14—H14B0.9300
C6—C71.542 (3)C12—H12A0.9700
C6—C51.543 (3)C12—H12B0.9700
C9—C81.325 (3)C3—H3A0.9700
C9—H90.9300C3—H3B0.9700
C8—C21.530 (2)C7—H7A0.9600
C11—C121.520 (3)C7—H7B0.9600
C11—H11A0.9700C7—H7C0.9600
C11—H11B0.9700C1—H1A0.9600
C13—C141.324 (3)C1—H1B0.9600
C2—C11.532 (4)C1—H1C0.9600
C15—O2—H2A111 (3)C4—C5—H5A108.9
O1—C15—O2123.21 (18)C6—C5—H5A108.9
O1—C15—C13123.4 (2)C4—C5—H5B108.9
O2—C15—C13113.44 (18)C6—C5—H5B108.9
C13—C10—C9112.69 (16)H5A—C5—H5B107.7
C13—C10—C11110.53 (17)C3—C4—C5110.32 (18)
C9—C10—C11110.32 (15)C3—C4—H4A109.6
C13—C10—H10107.7 (14)C5—C4—H4A109.6
C9—C10—H10107.7 (13)C3—C4—H4B109.6
C11—C10—H10107.7 (13)C5—C4—H4B109.6
C8—C6—C12109.20 (15)H4A—C4—H4B108.1
C8—C6—C7111.75 (17)C13—C14—H14A120.0
C12—C6—C7108.65 (18)C13—C14—H14B120.0
C8—C6—C5109.62 (17)H14A—C14—H14B120.0
C12—C6—C5107.66 (17)C11—C12—C6111.99 (17)
C7—C6—C5109.86 (17)C11—C12—H12A109.2
C8—C9—C10126.61 (17)C6—C12—H12A109.2
C8—C9—H9116.7C11—C12—H12B109.2
C10—C9—H9116.7C6—C12—H12B109.2
C9—C8—C6122.05 (15)H12A—C12—H12B107.9
C9—C8—C2119.63 (17)C4—C3—C2112.3 (2)
C6—C8—C2118.29 (16)C4—C3—H3A109.1
C12—C11—C10110.27 (18)C2—C3—H3A109.1
C12—C11—H11A109.6C4—C3—H3B109.1
C10—C11—H11A109.6C2—C3—H3B109.1
C12—C11—H11B109.6H3A—C3—H3B107.9
C10—C11—H11B109.6C6—C7—H7A109.5
H11A—C11—H11B108.1C6—C7—H7B109.5
C14—C13—C15118.89 (19)H7A—C7—H7B109.5
C14—C13—C10125.39 (17)C6—C7—H7C109.5
C15—C13—C10115.73 (16)H7A—C7—H7C109.5
C8—C2—C1112.89 (19)H7B—C7—H7C109.5
C8—C2—C3111.58 (18)C2—C1—H1A109.5
C1—C2—C3111.52 (18)C2—C1—H1B109.5
C8—C2—H2106.8 (14)H1A—C1—H1B109.5
C1—C2—H2106.8 (15)C2—C1—H1C109.5
C3—C2—H2106.8 (16)H1A—C1—H1C109.5
C4—C5—C6113.22 (19)H1B—C1—H1C109.5
C13—C10—C9—C8134.3 (2)C9—C10—C13—C15165.47 (17)
C11—C10—C9—C810.2 (3)C11—C10—C13—C1570.6 (2)
C10—C9—C8—C62.9 (3)C9—C8—C2—C199.2 (3)
C10—C9—C8—C2179.2 (2)C6—C8—C2—C182.7 (3)
C12—C6—C8—C916.3 (3)C9—C8—C2—C3134.3 (2)
C7—C6—C8—C9104.0 (2)C6—C8—C2—C343.8 (2)
C5—C6—C8—C9134.0 (2)C8—C6—C5—C451.0 (2)
C12—C6—C8—C2161.73 (18)C12—C6—C5—C4169.64 (19)
C7—C6—C8—C278.0 (2)C7—C6—C5—C472.2 (3)
C5—C6—C8—C244.0 (2)C6—C5—C4—C359.5 (3)
C13—C10—C11—C12167.21 (16)C10—C11—C12—C664.0 (2)
C9—C10—C11—C1241.9 (2)C8—C6—C12—C1149.0 (2)
O1—C15—C13—C14164.8 (2)C7—C6—C12—C1173.1 (2)
O2—C15—C13—C1414.9 (3)C5—C6—C12—C11167.97 (19)
O1—C15—C13—C1015.1 (3)C5—C4—C3—C257.8 (3)
O2—C15—C13—C10165.19 (18)C8—C2—C3—C449.2 (2)
C9—C10—C13—C1414.5 (3)C1—C2—C3—C478.0 (2)
C11—C10—C13—C14109.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14A···O20.932.332.673 (2)101
O2—H2A···O1i0.82 (1)1.91 (2)2.706 (2)162 (4)
Symmetry code: (i) x+1/2, y+3/2, z+2.
 

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