The title molecule, C
17H
14O, contains
p-methylbenzylidene and 1-indanone moieties. The 1-indanone moiety is nearly planar and it forms a dihedral angle of 7.2 (2)° with the plane through the methylphenyl ring. The crystal structure is stabilized by C—H
O intermolecular interactions.
Supporting information
CCDC reference: 185788
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.065
- wR factor = 0.197
- Data-to-parameter ratio = 15.1
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
WEIGH_01 Alert C Extra text has been found in the
_refine_ls_weighting_scheme field. This should be in the
_refine_ls_weighting_details field.
Weighting scheme given as calc w = 1/[\s^2^(Fo^2^)+(0.0785P)^2^] wher
Weighting scheme identified as calc
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
A vigorously stirred solution of aromatic aldehyde (0.01 mol) and 1-indanone
(0.01 mol) at room temperature was treated with 6 drops of saturated ethanolic
KOH. After 15 min, the mixture was heated with 95% ethanol (15 ml) and stirred
for 3 h. The resulting product was filtered and washed with 95% ethanol and
recrystallized from ethanol giving the title compound. Crystals suitable for
X-ray diffraction study were grown by slow evaporation from methanol.
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SDP (Frenz, 1978); data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Johnson & Burnett, 1998); software used to prepare material for publication: PARST97 (Nardelli, 1995).
2-(
p-methylbenzylindene)-1-indanone
top
Crystal data top
C17H14O | F(000) = 496 |
Mr = 234.28 | Dx = 1.231 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54180 Å |
a = 13.919 (2) Å | Cell parameters from 25 reflections |
b = 14.457 (3) Å | θ = 14–30° |
c = 6.308 (1) Å | µ = 0.58 mm−1 |
β = 95.07 (2)° | T = 293 K |
V = 1264.4 (4) Å3 | Needle, colourless |
Z = 4 | 0.20 × 0.10 × 0.05 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.079 |
Radiation source: fine-focus sealed tube | θmax = 71.9°, θmin = 3.2° |
Graphite monochromator | h = −17→17 |
ω–2θ scans | k = −17→0 |
2727 measured reflections | l = 0→7 |
2486 independent reflections | 3 standard reflections every 120min min |
804 reflections with I > 2σ(I) | intensity decay: <1% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.065 | H-atom parameters constrained |
wR(F2) = 0.197 | Calculated w = 1/[σ2(Fo2) + (0.0785P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.90 | (Δ/σ)max < 0.001 |
2486 reflections | Δρmax = 0.20 e Å−3 |
165 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0018 (5) |
Crystal data top
C17H14O | V = 1264.4 (4) Å3 |
Mr = 234.28 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 13.919 (2) Å | µ = 0.58 mm−1 |
b = 14.457 (3) Å | T = 293 K |
c = 6.308 (1) Å | 0.20 × 0.10 × 0.05 mm |
β = 95.07 (2)° | |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.079 |
2727 measured reflections | 3 standard reflections every 120min min |
2486 independent reflections | intensity decay: <1% |
804 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.065 | 0 restraints |
wR(F2) = 0.197 | H-atom parameters constrained |
S = 0.90 | Δρmax = 0.20 e Å−3 |
2486 reflections | Δρmin = −0.17 e Å−3 |
165 parameters | |
Special details top
Experimental. The poor ratio of observed to unique reflections may be due to poor diffraction
quality of the crystal. |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.2831 (2) | 0.0570 (2) | −0.0308 (5) | 0.0805 (11) | |
C1 | 0.2734 (3) | 0.0876 (3) | 0.1459 (7) | 0.0593 (12) | |
C2 | 0.3495 (3) | 0.1136 (3) | 0.3132 (6) | 0.0544 (12) | |
C3 | 0.3030 (3) | 0.1512 (3) | 0.5023 (6) | 0.0565 (12) | |
H3A | 0.3218 | 0.1156 | 0.6295 | 0.068* | |
H3B | 0.3202 | 0.2155 | 0.5278 | 0.068* | |
C4 | 0.1971 (3) | 0.1410 (3) | 0.4371 (7) | 0.0568 (12) | |
C5 | 0.1204 (3) | 0.1619 (3) | 0.5534 (8) | 0.0745 (14) | |
H5 | 0.1309 | 0.1856 | 0.6906 | 0.089* | |
C6 | 0.0287 (4) | 0.1471 (4) | 0.4631 (9) | 0.0919 (18) | |
H6 | −0.0231 | 0.1622 | 0.5401 | 0.110* | |
C7 | 0.0104 (4) | 0.1102 (4) | 0.2595 (10) | 0.0901 (17) | |
H7 | −0.0525 | 0.0995 | 0.2024 | 0.108* | |
C8 | 0.0869 (3) | 0.0899 (3) | 0.1454 (8) | 0.0763 (16) | |
H8 | 0.0765 | 0.0661 | 0.0083 | 0.092* | |
C9 | 0.1795 (3) | 0.1051 (3) | 0.2354 (7) | 0.0567 (12) | |
C10 | 0.4433 (3) | 0.1000 (3) | 0.2844 (7) | 0.0571 (12) | |
H10 | 0.4542 | 0.0770 | 0.1510 | 0.068* | |
C11 | 0.5299 (3) | 0.1150 (3) | 0.4246 (7) | 0.0512 (11) | |
C12 | 0.6185 (3) | 0.0895 (3) | 0.3575 (7) | 0.0595 (13) | |
H12 | 0.6203 | 0.0638 | 0.2228 | 0.071* | |
C13 | 0.7034 (3) | 0.1008 (3) | 0.4824 (8) | 0.0657 (13) | |
H13 | 0.7612 | 0.0818 | 0.4329 | 0.079* | |
C14 | 0.7032 (3) | 0.1404 (3) | 0.6824 (8) | 0.0576 (12) | |
C15 | 0.6166 (3) | 0.1663 (3) | 0.7516 (7) | 0.0619 (13) | |
H15 | 0.6153 | 0.1930 | 0.8855 | 0.074* | |
C16 | 0.5314 (3) | 0.1537 (3) | 0.6267 (7) | 0.0598 (12) | |
H16 | 0.4736 | 0.1714 | 0.6786 | 0.072* | |
C17 | 0.7956 (3) | 0.1537 (4) | 0.8219 (8) | 0.0838 (16) | |
H17A | 0.7826 | 0.1503 | 0.9687 | 0.126* | |
H17B | 0.8226 | 0.2131 | 0.7939 | 0.126* | |
H17C | 0.8406 | 0.1061 | 0.7922 | 0.126* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.094 (3) | 0.096 (3) | 0.050 (2) | 0.005 (2) | 0.0034 (17) | −0.015 (2) |
C1 | 0.084 (4) | 0.051 (3) | 0.043 (3) | 0.004 (3) | 0.005 (2) | 0.005 (2) |
C2 | 0.074 (3) | 0.041 (3) | 0.048 (3) | 0.003 (2) | 0.007 (2) | 0.008 (2) |
C3 | 0.067 (3) | 0.057 (3) | 0.046 (3) | 0.004 (2) | 0.008 (2) | −0.006 (2) |
C4 | 0.059 (3) | 0.055 (3) | 0.057 (3) | 0.002 (2) | 0.010 (2) | 0.000 (2) |
C5 | 0.071 (3) | 0.082 (4) | 0.070 (3) | −0.001 (3) | 0.008 (3) | −0.012 (3) |
C6 | 0.059 (4) | 0.108 (5) | 0.111 (5) | −0.002 (3) | 0.018 (3) | −0.019 (4) |
C7 | 0.063 (3) | 0.097 (5) | 0.110 (5) | −0.006 (3) | 0.003 (3) | −0.013 (4) |
C8 | 0.068 (3) | 0.081 (4) | 0.078 (4) | −0.003 (3) | −0.003 (3) | −0.004 (3) |
C9 | 0.062 (3) | 0.051 (3) | 0.058 (3) | 0.002 (2) | 0.007 (2) | 0.000 (2) |
C10 | 0.079 (3) | 0.044 (3) | 0.049 (3) | 0.002 (3) | 0.011 (2) | −0.001 (2) |
C11 | 0.060 (3) | 0.042 (3) | 0.053 (3) | −0.003 (2) | 0.012 (2) | −0.001 (2) |
C12 | 0.064 (3) | 0.051 (3) | 0.066 (3) | 0.003 (2) | 0.023 (3) | −0.003 (2) |
C13 | 0.068 (3) | 0.052 (3) | 0.080 (4) | 0.004 (3) | 0.019 (3) | 0.006 (3) |
C14 | 0.051 (3) | 0.045 (3) | 0.077 (3) | −0.001 (2) | 0.005 (2) | 0.006 (3) |
C15 | 0.063 (3) | 0.055 (3) | 0.070 (3) | 0.003 (3) | 0.012 (3) | −0.009 (2) |
C16 | 0.066 (3) | 0.052 (3) | 0.063 (3) | 0.001 (2) | 0.016 (2) | −0.007 (3) |
C17 | 0.061 (3) | 0.084 (4) | 0.105 (4) | 0.003 (3) | 0.002 (3) | −0.005 (3) |
Geometric parameters (Å, º) top
O1—C1 | 1.218 (5) | C8—H8 | 0.93 |
C1—C2 | 1.476 (6) | C10—C11 | 1.448 (5) |
C1—C9 | 1.490 (6) | C10—H10 | 0.93 |
C2—C10 | 1.348 (5) | C11—C12 | 1.388 (5) |
C2—C3 | 1.508 (5) | C11—C16 | 1.391 (5) |
C3—C4 | 1.502 (5) | C12—C13 | 1.371 (5) |
C3—H3A | 0.97 | C12—H12 | 0.93 |
C3—H3B | 0.97 | C13—C14 | 1.386 (6) |
C4—C9 | 1.376 (5) | C13—H13 | 0.93 |
C4—C5 | 1.381 (6) | C14—C15 | 1.370 (5) |
C5—C6 | 1.368 (6) | C14—C17 | 1.505 (5) |
C5—H5 | 0.93 | C15—C16 | 1.377 (5) |
C6—C7 | 1.393 (7) | C15—H15 | 0.93 |
C6—H6 | 0.93 | C16—H16 | 0.93 |
C7—C8 | 1.369 (6) | C17—H17A | 0.96 |
C7—H7 | 0.93 | C17—H17B | 0.96 |
C8—C9 | 1.380 (6) | C17—H17C | 0.96 |
| | | |
O1—C1—C2 | 128.1 (4) | C8—C9—C1 | 129.5 (5) |
O1—C1—C9 | 125.4 (4) | C2—C10—C11 | 131.3 (4) |
C2—C1—C9 | 106.5 (4) | C2—C10—H10 | 114.3 |
C10—C2—C1 | 120.6 (4) | C11—C10—H10 | 114.3 |
C10—C2—C3 | 130.3 (4) | C12—C11—C16 | 116.4 (4) |
C1—C2—C3 | 109.1 (4) | C12—C11—C10 | 119.2 (4) |
C4—C3—C2 | 103.2 (3) | C16—C11—C10 | 124.4 (4) |
C4—C3—H3A | 111.1 | C13—C12—C11 | 122.5 (5) |
C2—C3—H3A | 111.1 | C13—C12—H12 | 118.8 |
C4—C3—H3B | 111.1 | C11—C12—H12 | 118.8 |
C2—C3—H3B | 111.1 | C12—C13—C14 | 120.1 (5) |
H3A—C3—H3B | 109.1 | C12—C13—H13 | 120.0 |
C9—C4—C5 | 119.4 (4) | C14—C13—H13 | 120.0 |
C9—C4—C3 | 112.3 (4) | C15—C14—C13 | 118.4 (5) |
C5—C4—C3 | 128.3 (4) | C15—C14—C17 | 120.6 (5) |
C6—C5—C4 | 118.7 (5) | C13—C14—C17 | 121.0 (5) |
C6—C5—H5 | 120.6 | C14—C15—C16 | 121.3 (5) |
C4—C5—H5 | 120.6 | C14—C15—H15 | 119.4 |
C5—C6—C7 | 122.1 (5) | C16—C15—H15 | 119.4 |
C5—C6—H6 | 118.9 | C15—C16—C11 | 121.3 (4) |
C7—C6—H6 | 118.9 | C15—C16—H16 | 119.3 |
C8—C7—C6 | 118.6 (5) | C11—C16—H16 | 119.3 |
C8—C7—H7 | 120.7 | C14—C17—H17A | 109.5 |
C6—C7—H7 | 120.7 | C14—C17—H17B | 109.5 |
C7—C8—C9 | 119.4 (5) | H17A—C17—H17B | 109.5 |
C7—C8—H8 | 120.3 | C14—C17—H17C | 109.5 |
C9—C8—H8 | 120.3 | H17A—C17—H17C | 109.5 |
C4—C9—C8 | 121.6 (4) | H17B—C17—H17C | 109.5 |
C4—C9—C1 | 108.9 (4) | | |
| | | |
O1—C1—C2—C10 | −3.4 (7) | O1—C1—C9—C4 | −179.1 (4) |
C9—C1—C2—C10 | 175.8 (4) | C2—C1—C9—C4 | 1.7 (5) |
O1—C1—C2—C3 | 178.1 (4) | O1—C1—C9—C8 | 1.1 (8) |
C9—C1—C2—C3 | −2.6 (5) | C2—C1—C9—C8 | −178.1 (5) |
C10—C2—C3—C4 | −175.7 (4) | C1—C2—C10—C11 | −176.7 (4) |
C1—C2—C3—C4 | 2.5 (5) | C3—C2—C10—C11 | 1.4 (8) |
C2—C3—C4—C9 | −1.5 (5) | C2—C10—C11—C12 | 176.1 (4) |
C2—C3—C4—C5 | 177.6 (4) | C2—C10—C11—C16 | −3.7 (7) |
C9—C4—C5—C6 | −0.7 (7) | C16—C11—C12—C13 | 0.5 (6) |
C3—C4—C5—C6 | −179.9 (4) | C10—C11—C12—C13 | −179.3 (4) |
C4—C5—C6—C7 | 1.2 (8) | C11—C12—C13—C14 | −1.2 (7) |
C5—C6—C7—C8 | −1.3 (9) | C12—C13—C14—C15 | 0.9 (7) |
C6—C7—C8—C9 | 1.0 (8) | C12—C13—C14—C17 | −179.9 (4) |
C5—C4—C9—C8 | 0.5 (7) | C13—C14—C15—C16 | −0.1 (7) |
C3—C4—C9—C8 | 179.8 (4) | C17—C14—C15—C16 | −179.3 (4) |
C5—C4—C9—C1 | −179.3 (4) | C14—C15—C16—C11 | −0.7 (7) |
C3—C4—C9—C1 | 0.0 (5) | C12—C11—C16—C15 | 0.5 (6) |
C7—C8—C9—C4 | −0.6 (7) | C10—C11—C16—C15 | −179.8 (4) |
C7—C8—C9—C1 | 179.1 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3A···O1i | 0.97 | 2.41 | 3.279 (5) | 149 |
C12—H12···O1ii | 0.93 | 2.57 | 3.333 (5) | 139 |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y, −z. |
Experimental details
Crystal data |
Chemical formula | C17H14O |
Mr | 234.28 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 13.919 (2), 14.457 (3), 6.308 (1) |
β (°) | 95.07 (2) |
V (Å3) | 1264.4 (4) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.58 |
Crystal size (mm) | 0.20 × 0.10 × 0.05 |
|
Data collection |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2727, 2486, 804 |
Rint | 0.079 |
(sin θ/λ)max (Å−1) | 0.616 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.065, 0.197, 0.90 |
No. of reflections | 2486 |
No. of parameters | 165 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.17 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3A···O1i | 0.97 | 2.41 | 3.279 (5) | 149.1 |
C12—H12···O1ii | 0.93 | 2.57 | 3.333 (5) | 139.4 |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y, −z. |
Indanone derivatives have been studied on account of the well known anticoagulant activity in the vitamin K dependent biosynthesis (Ernster et al., 1972; Bravic et al., 1974a,b; Csoregh & Eckstein, 1979). Some of the derivatives have also been shown to be charge-transfer complexes (Silverman et al., 1974) and the 1-indanone system has a particular propensity to produce catemers in the solid state (Brunskill et al., 1997; Lalancette, 1998). 2-Benzylidene-1-indanone has been used as the starting material to produce dimeric products (Berthelette et al., 1997; Houlihan et al., 1997). In view of these features associated with the indanone moiety, the structure determination of the 2-(p-methylbenzylidene)-1-indanone, (I), was undertaken.
The bond lengths and angles observed in (I) agree with the corresponding values observed for 2-benzylidene-1-indanone (Hoser et al., 1980). The 1-indanone moiety is nearly planar, with atom C2 deviating by a maximum of 0.033 (4) Å. The values of the O1—C1—C2—C10 [-3.4 (7)°], C1—C2—C10—C11 [-176.7 (4)°], C2—C10—C11—C16 [-3.7 (7)°] and C1—C2—C3—C4 [2.5 (5) Å] torsion angles show that the molecule as a whole is slightly distorted from planarity. The conformation of the molecule as a whole can be described conveniently by the dihedral angle between the planes of the two phenyl rings (Katrusiak et al., 1987). In the title molecule, it is found to be 7.5 (2)°. This angle is 15.3° for 2-benzylidene-1-indanone (Hoser et al., 1980), 11.4° for chalcone (Rabinovich 1970), 52.9° for 2-benzylidene-1-tetralone (Kaluski et al., 1978) and 59.1° for 3-benzylidene-4-chromanone (Katrusiak et al., 1987). This shows that the title molecule is flatter than the molecule of 2-benzylidene-1-indanone. Spectroscopic investigations (IR, UV, NMR) of arylidene derivatives of 1-tetralone and 4-chromanone showed that an increase in the electron interactions of electron-donor substituents in a conjugated bond system leads to flattening of the molecules (Orlov, Borovoi & Lavrushin, 1976; Orlov, Borovoi, Surov & Lavrushin, 1976). Fig. 2 shows the packing of the molecules viewed down the a axis. In the crystal, the molecules translated along the c-cell direction are linked by C3—H3A···O1i [symmetry code: (i) x, y, 1 + z] hydrogen bonds to form an infinite one-dimensional chain. The molecules of the adjacent inversion related chains are linked by centrosymmetric C12—H12···O1ii [symmetry code: (ii) 1 - x, -y, -z] hydrogen bonds to form a molecular column down the c axis (Table 1).