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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
CCDC reference: 248854
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (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
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.
Crystal data top
C19H18O | F(000) = 280.00 |
Mr = 262.35 | Dx = 1.199 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: C 2y | Cell parameters from 2926 reflections |
a = 10.5362 (6) Å | θ = 3.7–27.3° |
b = 6.5254 (2) Å | µ = 0.07 mm−1 |
c = 10.6656 (4) Å | T = 296 K |
β = 97.790 (1)° | Chunk, colorless |
V = 726.52 (5) Å3 | 0.33 × 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-1 | Rint = 0.027 |
ω scans | θmax = 27.4° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −13→13 |
Tmin = 0.953, Tmax = 0.988 | k = −8→8 |
3380 measured reflections | l = −13→13 |
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) = 0.099 | Δρmax = 0.13 e Å−3 |
S = 1.01 | Δρmin = −0.10 e Å−3 |
715 reflections | Extinction correction: (Larson, 1970) |
102 parameters | Extinction 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 | x | y | z | Uiso*/Ueq | |
O1 | 0.5000 | 0.6124 (4) | 0.0000 | 0.0662 (7) | |
C1 | 0.5000 | 0.4260 (4) | 0.0000 | 0.0425 (7) | |
C2 | 0.6019 (2) | 0.3144 (3) | 0.0852 (2) | 0.0412 (4) | |
C3 | 0.7250 (2) | 0.4321 (4) | 0.1172 (2) | 0.0596 (6) | |
C4 | 0.5746 (2) | 0.1344 (3) | 0.1360 (2) | 0.0417 (4) | |
C5 | 0.6549 (2) | 0.0101 (3) | 0.2308 (1) | 0.0437 (5) | |
C6 | 0.5936 (2) | −0.1120 (4) | 0.3113 (2) | 0.0571 (6) | |
C7 | 0.6622 (3) | −0.2312 (4) | 0.4030 (2) | 0.0718 (7) | |
C8 | 0.7944 (3) | −0.2358 (4) | 0.4148 (2) | 0.0701 (7) | |
C9 | 0.8567 (2) | −0.1211 (4) | 0.3341 (2) | 0.0615 (6) | |
C10 | 0.7887 (2) | 0.0022 (4) | 0.2428 (2) | 0.0506 (5) | |
H1 | 0.7824 | 0.4044 | 0.0553 | 0.070* | |
H2 | 0.7657 | 0.3912 | 0.2005 | 0.070* | |
H3 | 0.7058 | 0.5774 | 0.1174 | 0.071* | |
H4 | 0.4903 | 0.0793 | 0.1069 | 0.049* | |
H5 | 0.5007 | −0.1156 | 0.3013 | 0.068* | |
H6 | 0.6173 | −0.3098 | 0.4605 | 0.085* | |
H7 | 0.8416 | −0.3196 | 0.4804 | 0.081* | |
H8 | 0.9493 | −0.1283 | 0.3410 | 0.072* | |
H9 | 0.8332 | 0.0839 | 0.1865 | 0.060* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.064 (1) | 0.042 (1) | 0.088 (2) | 0.0000 | −0.003 (1) | 0.0000 |
C1 | 0.044 (1) | 0.039 (2) | 0.045 (1) | 0.0000 | 0.009 (1) | 0.0000 |
C2 | 0.0377 (9) | 0.043 (1) | 0.0422 (8) | −0.0039 (7) | 0.0038 (6) | −0.0051 (8) |
C3 | 0.051 (1) | 0.049 (1) | 0.074 (1) | −0.013 (1) | −0.0071 (9) | 0.001 (1) |
C4 | 0.0351 (8) | 0.047 (1) | 0.0421 (8) | −0.0038 (7) | 0.0007 (6) | −0.0025 (8) |
C5 | 0.0484 (9) | 0.041 (1) | 0.0401 (8) | −0.0019 (9) | −0.0011 (7) | −0.0047 (9) |
C6 | 0.059 (1) | 0.058 (1) | 0.053 (1) | −0.007 (1) | 0.0027 (9) | 0.006 (1) |
C7 | 0.092 (2) | 0.061 (2) | 0.060 (1) | −0.005 (1) | 0.004 (1) | 0.019 (1) |
C8 | 0.090 (2) | 0.058 (1) | 0.055 (1) | 0.009 (1) | −0.018 (1) | 0.005 (1) |
C9 | 0.060 (1) | 0.060 (1) | 0.059 (1) | 0.011 (1) | −0.0124 (9) | −0.008 (1) |
C10 | 0.048 (1) | 0.053 (1) | 0.0488 (9) | 0.0004 (9) | −0.0004 (7) | −0.005 (1) |
Geometric parameters (Å, º) top
O1—C1 | 1.217 (4) | C9—C10 | 1.386 (3) |
C1—C2 | 1.498 (2) | C3—H1 | 0.9700 |
C1—C2i | 1.498 (2) | C3—H2 | 0.9700 |
C2—C3 | 1.506 (3) | C3—H3 | 0.9700 |
C2—C4 | 1.341 (3) | C4—H4 | 0.9700 |
C4—C5 | 1.471 (2) | C6—H5 | 0.9700 |
C5—C6 | 1.393 (3) | C7—H6 | 0.9700 |
C5—C10 | 1.399 (3) | C8—H7 | 0.9700 |
C6—C7 | 1.376 (3) | C9—H8 | 0.9700 |
C7—C8 | 1.382 (4) | C10—H9 | 0.9700 |
C8—C9 | 1.373 (4) | | |
| | | |
O1—C1—C2 | 119.1 (1) | C2—C3—H2 | 109.0690 |
O1—C1—C2i | 119.1 (1) | C2—C3—H3 | 108.9685 |
C2i—C1—C2 | 121.8 (2) | C2—C4—H4 | 115.6234 |
C1—C2—C3 | 114.4 (2) | H2—C3—H1 | 109.4721 |
C1—C2—C4 | 119.7 (2) | H3—C3—H1 | 109.4736 |
C1—C2i—C3i | 114.4 (2) | H3—C3—H2 | 109.4697 |
C1—C2i—C4i | 119.7 (2) | H4—C4—C5 | 115.6034 |
C4—C2—C3 | 125.5 (2) | C5—C6—H5 | 119.4133 |
C2—C4—C5 | 128.8 (2) | C5—C10—H9 | 119.2537 |
C4—C5—C10 | 124.2 (2) | H5—C6—C7 | 119.3441 |
C4—C5—C6 | 117.9 (2) | C6—C7—H6 | 119.5975 |
C10—C5—C6 | 117.9 (2) | H6—C7—C8 | 120.1529 |
C5—C6—C7 | 121.2 (2) | C7—C8—H7 | 119.3709 |
C5—C10—C9 | 120.3 (2) | C8—C9—H8 | 119.2280 |
C6—C7—C8 | 120.2 (2) | H7—C8—C9 | 121.1287 |
C7—C8—C9 | 119.5 (2) | C9—C10—H9 | 120.4540 |
C8—C9—C10 | 120.8 (2) | H8—C9—C10 | 119.9905 |
C2—C3—H1 | 110.3706 | | |
| | | |
O1—C1—C2—C3 | −26.63 (19) | C10—C5—C6—C7 | 2.4 (3) |
O1—C1—C2—C4 | 146.83 (11) | C4—C5—C6—C7 | −179.4 (2) |
C2i—C1—C2—C3 | 153.47 (14) | C4—C5—C10—C9 | −179.3 (2) |
C2i—C1—C2—C4 | −33.17 (14) | C5—C6—C7—C8 | −1.6 (4) |
C1—C2—C4—C5 | −173.38 (12) | C6—C7—C8—C9 | −0.2 (4) |
C3—C2—C4—C5 | −0.8 (2) | C7—C8—C9—C10 | 1.4 (4) |
C2—C4—C5—C6 | 150.47 (12) | C8—C9—C10—C5 | −0.6 (4) |
C2—C4—C5—C10 | −31.5 (2) | | |
Symmetry code: (i) −x+1, y, −z. |
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