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The title compound, C16H18O2, an acyl­cylopropane, has no unusual bonding features. In the crystal structure, dimers are formed via a weak C—H...O hydrogen-bonding inter­action involving a C—H of the phenyl ring and a carbonyl group of a neighbouring molecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807013815/su2005sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807013815/su2005Isup2.hkl
Contains datablock I

CCDC reference: 647346

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.043
  • wR factor = 0.120
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT480_ALERT_4_C Long H...A H-Bond Reported H12 .. O2 .. 2.78 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H8A .. O1 .. 2.74 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H13 .. O1 .. 2.79 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H7A .. O2 .. 2.80 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H13 .. O1 .. 2.67 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H10A .. O2 .. 2.83 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H7B .. O1 .. 2.72 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C10 .. O2 .. 3.74 Ang. PLAT482_ALERT_4_C Small D-H..A Angle Rep for C12 .. O2 .. 91.47 Deg. PLAT482_ALERT_4_C Small D-H..A Angle Rep for C8 .. O1 .. 96.74 Deg. PLAT758_ALERT_4_C D-H..A Calc 91.00, Rep 91.47(8) ...... Senseless su C12 -H12 -O2 1.555 1.555 1.555 PLAT758_ALERT_4_C D-H..A Calc 97.00, Rep 96.74(9) ...... Senseless su C8 -H8A -O1 1.555 1.555 1.555
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 0 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 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 1 ALERT type 3 Indicator that the structure quality may be low 12 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(1R*,2R*,2'S*,4S*)-2'-methoxy-3-oxo-2'- phenylspiro(bicyclo[2.2.1]heptane-2,1'-cyclopropane) top
Crystal data top
C16H18O2F(000) = 520
Mr = 242.32Dx = 1.251 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybcCell parameters from 2235 reflections
a = 9.4822 (1) Åθ = 2.0–70.0°
b = 20.6081 (3) ŵ = 0.64 mm1
c = 6.9712 (1) ÅT = 293 K
β = 109.246 (1)°Prismatic, white
V = 1286.11 (3) Å30.37 × 0.37 × 0.20 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector
diffractometer
2562 independent reflections
Radiation source: fine-focus sealed tube2126 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Detector resolution: 9 pixels mm-1θmax = 72.8°, θmin = 4.4°
ω scansh = 1110
Absorption correction: part of the refinement model (ΔF)
(XABS2; Parkin et al., 1995)
k = 024
Tmin = 0.791, Tmax = 0.878l = 08
17858 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.120 w = 1/[σ2(Fo2) + (0.0679P)2 + 0.2503P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2350 reflectionsΔρmax = 0.22 e Å3
164 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.021 (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
xyzUiso*/Ueq
C50.13936 (16)0.82611 (8)0.5031 (3)0.0596 (4)
H5A0.12630.80980.62670.072*
H5B0.12870.79050.40840.072*
O20.49092 (10)0.93124 (4)0.21454 (14)0.0463 (3)
O10.16180 (11)0.94276 (5)0.07581 (15)0.0572 (3)
C110.60569 (14)0.86049 (6)0.50298 (19)0.0406 (3)
C20.19841 (14)0.92379 (6)0.2497 (2)0.0436 (3)
C130.80756 (16)0.89609 (8)0.7980 (2)0.0518 (4)
H130.85400.92890.88840.062*
C30.12840 (16)0.94001 (7)0.4091 (2)0.0519 (4)
H30.08060.98270.39620.062*
C120.67665 (15)0.90870 (7)0.6409 (2)0.0461 (3)
H120.63530.95010.62720.055*
C10.31558 (13)0.87368 (6)0.34768 (19)0.0420 (3)
C60.29187 (15)0.85971 (7)0.5483 (2)0.0487 (4)
H60.37540.83780.64970.058*
C100.58736 (18)0.91794 (9)0.1011 (2)0.0620 (4)
H10A0.59800.95620.02860.093*
H10C0.54580.88360.00620.093*
H10B0.68350.90500.19170.093*
C40.02655 (16)0.88112 (8)0.4082 (3)0.0591 (4)
H4A0.03710.88980.48940.071*
H4B0.03550.87020.27100.071*
C70.25814 (18)0.92821 (7)0.6069 (2)0.0556 (4)
H7A0.34060.95800.62460.067*
H7B0.22690.92870.72610.067*
C160.66834 (16)0.79907 (7)0.5289 (2)0.0514 (4)
H160.62230.76600.43950.062*
C90.47007 (14)0.87742 (6)0.32628 (19)0.0408 (3)
C80.36199 (15)0.82633 (7)0.2144 (2)0.0529 (4)
H8B0.38180.78190.26160.064*
H8A0.31710.83100.06840.064*
C140.86904 (17)0.83474 (8)0.8203 (2)0.0555 (4)
H140.95750.82620.92520.067*
C150.79962 (18)0.78645 (8)0.6877 (2)0.0594 (4)
H150.84050.74500.70400.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C50.0541 (8)0.0524 (9)0.0756 (10)0.0080 (7)0.0256 (8)0.0082 (7)
O20.0476 (5)0.0477 (6)0.0460 (5)0.0042 (4)0.0189 (4)0.0066 (4)
O10.0527 (6)0.0692 (7)0.0459 (6)0.0082 (5)0.0112 (4)0.0079 (5)
C110.0417 (6)0.0384 (7)0.0439 (7)0.0011 (5)0.0171 (5)0.0019 (5)
C20.0411 (7)0.0422 (7)0.0455 (7)0.0034 (5)0.0114 (5)0.0017 (5)
C130.0509 (8)0.0566 (9)0.0447 (7)0.0031 (6)0.0112 (6)0.0007 (6)
C30.0566 (8)0.0445 (8)0.0596 (9)0.0056 (6)0.0261 (7)0.0008 (6)
C120.0489 (7)0.0395 (7)0.0477 (7)0.0006 (5)0.0129 (6)0.0015 (5)
C10.0402 (6)0.0365 (7)0.0466 (7)0.0028 (5)0.0107 (5)0.0028 (5)
C60.0469 (7)0.0461 (8)0.0514 (8)0.0028 (6)0.0140 (6)0.0075 (6)
C100.0584 (9)0.0810 (11)0.0519 (8)0.0078 (8)0.0254 (7)0.0074 (8)
C40.0487 (8)0.0661 (10)0.0671 (10)0.0009 (7)0.0254 (7)0.0054 (8)
C70.0677 (9)0.0562 (9)0.0475 (8)0.0095 (7)0.0254 (7)0.0048 (6)
C160.0529 (8)0.0415 (7)0.0588 (8)0.0048 (6)0.0173 (6)0.0025 (6)
C90.0432 (7)0.0352 (7)0.0438 (7)0.0008 (5)0.0142 (5)0.0026 (5)
C80.0515 (8)0.0432 (8)0.0582 (8)0.0001 (6)0.0101 (6)0.0132 (6)
C140.0491 (8)0.0670 (10)0.0477 (8)0.0091 (7)0.0124 (6)0.0104 (7)
C150.0599 (9)0.0508 (9)0.0664 (9)0.0182 (7)0.0193 (7)0.0111 (7)
Geometric parameters (Å, º) top
C5—C61.5392 (19)C1—C61.5158 (19)
C5—C41.549 (2)C1—C91.5225 (17)
C5—H5A0.9700C6—C71.532 (2)
C5—H5B0.9700C6—H60.9800
O2—C91.4063 (15)C10—H10A0.9600
O2—C101.4191 (18)C10—H10C0.9600
O1—C21.2107 (16)C10—H10B0.9600
C11—C161.3845 (19)C4—H4A0.9700
C11—C121.3921 (19)C4—H4B0.9700
C11—C91.4995 (18)C7—H7A0.9700
C2—C11.5057 (18)C7—H7B0.9700
C2—C31.507 (2)C16—C151.391 (2)
C13—C141.379 (2)C16—H160.9300
C13—C121.3826 (19)C9—C81.4966 (18)
C13—H130.9300C8—H8B0.9700
C3—C71.535 (2)C8—H8A0.9700
C3—C41.550 (2)C14—C151.370 (2)
C3—H30.9800C14—H140.9300
C12—H120.9300C15—H150.9300
C1—C81.5093 (19)
C6—C5—C4103.19 (12)O2—C10—H10C109.5
C6—C5—H5A111.1H10A—C10—H10C109.5
C4—C5—H5A111.1O2—C10—H10B109.5
C6—C5—H5B111.1H10A—C10—H10B109.5
C4—C5—H5B111.1H10C—C10—H10B109.5
H5A—C5—H5B109.1C5—C4—C3103.27 (11)
C9—O2—C10112.98 (11)C5—C4—H4A111.1
C16—C11—C12118.25 (12)C3—C4—H4A111.1
C16—C11—C9122.34 (12)C5—C4—H4B111.1
C12—C11—C9119.33 (11)C3—C4—H4B111.1
O1—C2—C1126.92 (13)H4A—C4—H4B109.1
O1—C2—C3128.01 (13)C6—C7—C394.73 (11)
C1—C2—C3104.85 (11)C6—C7—H7A112.8
C14—C13—C12119.81 (14)C3—C7—H7A112.8
C14—C13—H13120.1C6—C7—H7B112.8
C12—C13—H13120.1C3—C7—H7B112.8
C2—C3—C7102.11 (11)H7A—C7—H7B110.2
C2—C3—C4104.40 (12)C11—C16—C15120.53 (14)
C7—C3—C4101.15 (12)C11—C16—H16119.7
C2—C3—H3115.7C15—C16—H16119.7
C7—C3—H3115.7O2—C9—C8117.61 (11)
C4—C3—H3115.7O2—C9—C11113.54 (10)
C13—C12—C11121.09 (13)C8—C9—C11121.26 (11)
C13—C12—H12119.5O2—C9—C1114.18 (10)
C11—C12—H12119.5C8—C9—C159.98 (9)
C2—C1—C8119.05 (11)C11—C9—C1120.00 (11)
C2—C1—C6103.71 (11)C9—C8—C160.86 (8)
C8—C1—C6127.39 (12)C9—C8—H8B117.7
C2—C1—C9120.72 (11)C1—C8—H8B117.7
C8—C1—C959.16 (8)C9—C8—H8A117.7
C6—C1—C9122.70 (11)C1—C8—H8A117.7
C1—C6—C7100.28 (11)H8B—C8—H8A114.8
C1—C6—C5108.15 (12)C15—C14—C13119.91 (14)
C7—C6—C5101.80 (12)C15—C14—H14120.0
C1—C6—H6115.0C13—C14—H14120.0
C7—C6—H6115.0C14—C15—C16120.40 (14)
C5—C6—H6115.0C14—C15—H15119.8
O2—C10—H10A109.5C16—C15—H15119.8
O1—C2—C3—C7155.69 (14)C4—C3—C7—C655.49 (12)
C1—C2—C3—C729.46 (13)C12—C11—C16—C150.7 (2)
O1—C2—C3—C499.28 (17)C9—C11—C16—C15175.88 (13)
C1—C2—C3—C475.57 (13)C10—O2—C9—C879.35 (14)
C14—C13—C12—C110.5 (2)C10—O2—C9—C1170.72 (14)
C16—C11—C12—C131.0 (2)C10—O2—C9—C1146.76 (12)
C9—C11—C12—C13175.64 (12)C16—C11—C9—O2125.26 (13)
O1—C2—C1—C820.7 (2)C12—C11—C9—O251.27 (15)
C3—C2—C1—C8154.22 (12)C16—C11—C9—C823.59 (19)
O1—C2—C1—C6168.96 (13)C12—C11—C9—C8159.88 (12)
C3—C2—C1—C65.96 (13)C16—C11—C9—C194.60 (15)
O1—C2—C1—C948.69 (19)C12—C11—C9—C188.86 (15)
C3—C2—C1—C9136.39 (12)C2—C1—C9—O21.46 (16)
C2—C1—C6—C739.18 (13)C8—C1—C9—O2109.10 (12)
C8—C1—C6—C7176.18 (12)C6—C1—C9—O2133.70 (12)
C9—C1—C6—C7102.21 (14)C2—C1—C9—C8107.65 (14)
C2—C1—C6—C566.97 (13)C6—C1—C9—C8117.20 (14)
C8—C1—C6—C577.67 (16)C2—C1—C9—C11141.35 (12)
C9—C1—C6—C5151.64 (12)C8—C1—C9—C11111.00 (13)
C4—C5—C6—C170.26 (15)C6—C1—C9—C116.20 (18)
C4—C5—C6—C734.83 (15)O2—C9—C8—C1103.40 (12)
C6—C5—C4—C30.33 (16)C11—C9—C8—C1108.96 (13)
C2—C3—C4—C570.52 (15)C2—C1—C8—C9110.42 (13)
C7—C3—C4—C535.22 (15)C6—C1—C8—C9109.61 (14)
C1—C6—C7—C355.52 (12)C12—C13—C14—C150.5 (2)
C5—C6—C7—C355.66 (13)C13—C14—C15—C160.8 (2)
C2—C3—C7—C652.06 (12)C11—C16—C15—C140.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O20.932.782.950 (1)92 (1)
C8—H8A···O10.972.743.014 (2)97 (1)
C13—H13···O1i0.932.793.416 (2)126 (1)
C7—H7A···O2ii0.972.803.694 (2)154 (1)
C13—H13···O1ii0.932.673.423 (2)139 (1)
C10—H10A···O2iii0.962.833.738 (2)158 (1)
C7—H7B···O1iv0.972.723.685 (2)173 (1)
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y+2, z+1; (iii) x+1, y+2, z; (iv) x, y, z+1.
 

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