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In the crystal structure of the title compound, C19H18O, there is one-half mol­ecule in the asymmetric unit and the carbonyl group is located on a crystallographic twofold rotation axis. The olefinic bond is in an anti configuration.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804018021/ob6395sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804018021/ob6395Isup2.hkl
Contains datablock I

CCDC reference: 248854

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.034
  • wR factor = 0.099
  • Data-to-parameter ratio = 7.0

checkCIF/PLATON results

No syntax errors found



Alert level C REFNR01_ALERT_3_C Ratio of reflections to parameters is < 8 for a non-centrosymmetric structure, where ZMAX < 18 sine(theta)/lambda 0.6482 Proportion of unique data used 0.7909 Ratio reflections to parameters 7.0098 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.01
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 27.43 From the CIF: _reflns_number_total 904 Count of symmetry unique reflns 905 Completeness (_total/calc) 99.89% 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 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

(I) top
Crystal data top
C19H18OF(000) = 280.00
Mr = 262.35Dx = 1.199 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.7107 Å
Hall symbol: C 2yCell parameters from 2926 reflections
a = 10.5362 (6) Åθ = 3.7–27.3°
b = 6.5254 (2) ŵ = 0.07 mm1
c = 10.6656 (4) ÅT = 296 K
β = 97.790 (1)°Chunk, colorless
V = 726.52 (5) Å30.33 × 0.30 × 0.17 mm
Z = 2
Data collection top
Rigaku R-AXIS RAPID
diffractometer
715 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.027
ω scansθmax = 27.4°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1313
Tmin = 0.953, Tmax = 0.988k = 88
3380 measured reflectionsl = 1313
904 independent reflections
Refinement top
Refinement on F2 w = 1/[0.0019Fo2 + σ(Fo2)]/(4Fo2)
R[F2 > 2σ(F2)] = 0.034(Δ/σ)max < 0.001
wR(F2) = 0.099Δρmax = 0.13 e Å3
S = 1.01Δρmin = 0.10 e Å3
715 reflectionsExtinction correction: (Larson, 1970)
102 parametersExtinction coefficient: 304 (46)
H-atom parameters constrained
Special details top

Refinement. Refinement using reflections with F2 > 2.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.50000.6124 (4)0.00000.0662 (7)
C10.50000.4260 (4)0.00000.0425 (7)
C20.6019 (2)0.3144 (3)0.0852 (2)0.0412 (4)
C30.7250 (2)0.4321 (4)0.1172 (2)0.0596 (6)
C40.5746 (2)0.1344 (3)0.1360 (2)0.0417 (4)
C50.6549 (2)0.0101 (3)0.2308 (1)0.0437 (5)
C60.5936 (2)0.1120 (4)0.3113 (2)0.0571 (6)
C70.6622 (3)0.2312 (4)0.4030 (2)0.0718 (7)
C80.7944 (3)0.2358 (4)0.4148 (2)0.0701 (7)
C90.8567 (2)0.1211 (4)0.3341 (2)0.0615 (6)
C100.7887 (2)0.0022 (4)0.2428 (2)0.0506 (5)
H10.78240.40440.05530.070*
H20.76570.39120.20050.070*
H30.70580.57740.11740.071*
H40.49030.07930.10690.049*
H50.50070.11560.30130.068*
H60.61730.30980.46050.085*
H70.84160.31960.48040.081*
H80.94930.12830.34100.072*
H90.83320.08390.18650.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.064 (1)0.042 (1)0.088 (2)0.00000.003 (1)0.0000
C10.044 (1)0.039 (2)0.045 (1)0.00000.009 (1)0.0000
C20.0377 (9)0.043 (1)0.0422 (8)0.0039 (7)0.0038 (6)0.0051 (8)
C30.051 (1)0.049 (1)0.074 (1)0.013 (1)0.0071 (9)0.001 (1)
C40.0351 (8)0.047 (1)0.0421 (8)0.0038 (7)0.0007 (6)0.0025 (8)
C50.0484 (9)0.041 (1)0.0401 (8)0.0019 (9)0.0011 (7)0.0047 (9)
C60.059 (1)0.058 (1)0.053 (1)0.007 (1)0.0027 (9)0.006 (1)
C70.092 (2)0.061 (2)0.060 (1)0.005 (1)0.004 (1)0.019 (1)
C80.090 (2)0.058 (1)0.055 (1)0.009 (1)0.018 (1)0.005 (1)
C90.060 (1)0.060 (1)0.059 (1)0.011 (1)0.0124 (9)0.008 (1)
C100.048 (1)0.053 (1)0.0488 (9)0.0004 (9)0.0004 (7)0.005 (1)
Geometric parameters (Å, º) top
O1—C11.217 (4)C9—C101.386 (3)
C1—C21.498 (2)C3—H10.9700
C1—C2i1.498 (2)C3—H20.9700
C2—C31.506 (3)C3—H30.9700
C2—C41.341 (3)C4—H40.9700
C4—C51.471 (2)C6—H50.9700
C5—C61.393 (3)C7—H60.9700
C5—C101.399 (3)C8—H70.9700
C6—C71.376 (3)C9—H80.9700
C7—C81.382 (4)C10—H90.9700
C8—C91.373 (4)
O1—C1—C2119.1 (1)C2—C3—H2109.0690
O1—C1—C2i119.1 (1)C2—C3—H3108.9685
C2i—C1—C2121.8 (2)C2—C4—H4115.6234
C1—C2—C3114.4 (2)H2—C3—H1109.4721
C1—C2—C4119.7 (2)H3—C3—H1109.4736
C1—C2i—C3i114.4 (2)H3—C3—H2109.4697
C1—C2i—C4i119.7 (2)H4—C4—C5115.6034
C4—C2—C3125.5 (2)C5—C6—H5119.4133
C2—C4—C5128.8 (2)C5—C10—H9119.2537
C4—C5—C10124.2 (2)H5—C6—C7119.3441
C4—C5—C6117.9 (2)C6—C7—H6119.5975
C10—C5—C6117.9 (2)H6—C7—C8120.1529
C5—C6—C7121.2 (2)C7—C8—H7119.3709
C5—C10—C9120.3 (2)C8—C9—H8119.2280
C6—C7—C8120.2 (2)H7—C8—C9121.1287
C7—C8—C9119.5 (2)C9—C10—H9120.4540
C8—C9—C10120.8 (2)H8—C9—C10119.9905
C2—C3—H1110.3706
O1—C1—C2—C326.63 (19)C10—C5—C6—C72.4 (3)
O1—C1—C2—C4146.83 (11)C4—C5—C6—C7179.4 (2)
C2i—C1—C2—C3153.47 (14)C4—C5—C10—C9179.3 (2)
C2i—C1—C2—C433.17 (14)C5—C6—C7—C81.6 (4)
C1—C2—C4—C5173.38 (12)C6—C7—C8—C90.2 (4)
C3—C2—C4—C50.8 (2)C7—C8—C9—C101.4 (4)
C2—C4—C5—C6150.47 (12)C8—C9—C10—C50.6 (4)
C2—C4—C5—C1031.5 (2)
Symmetry code: (i) x+1, y, z.
 

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