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The molecule of the title compound [systematic name: 3-(4-methyl­phen­yl)-1-phenyl­prop-2-enone], C16H14O, displays a significant deviation from planarity; the torsion angle of the carbonyl oxygen and the three enone C atoms is 16.3 (3)°, while the dihedral angle between the two benzene rings is 50.7 (2)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806050070/tk2107sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806050070/tk2107Isup2.hkl
Contains datablock I

CCDC reference: 630493

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.050
  • wR factor = 0.148
  • Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 61.80 Deg.
Author Response: The limitiation of the Chi circle of the P4 goniometer restrictred 2theta data collection to 61.79 degrees.

Alert level B THETM01_ALERT_3_B The value of sine(theta_max)/wavelength is less than 0.575 Calculated sin(theta_max)/wavelength = 0.5716 PLAT023_ALERT_3_B Resolution (too) Low [sin(th)/Lambda < 0.6]..... 61.80 Deg.
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: XSCANS (Bruker, 1999); cell refinement: XSCANS; data reduction: XPREP (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: X-SEED.

3-(4-methylphenyl)-1-phenyl-2-propenone top
Crystal data top
C16H14OF(000) = 472
Mr = 222.27Dx = 1.203 Mg m3
Monoclinic, P21/nMelting point = 367–369.3 K
Hall symbol: -P 2ynCu Kα radiation, λ = 1.54178 Å
a = 5.8601 (6) ÅCell parameters from 33 reflections
b = 16.732 (2) Åθ = 8.9–29.5°
c = 12.5363 (16) ŵ = 0.57 mm1
β = 93.522 (9)°T = 298 K
V = 1226.9 (2) Å3Block, pale yellow
Z = 40.48 × 0.16 × 0.12 mm
Data collection top
Bruker P4
diffractometer
1398 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.069
Graphite monochromatorθmax = 61.8°, θmin = 4.4°
θ/2θ\ scansh = 16
Absorption correction: analytical
(XPREP; Bruker, 1999)
k = 119
Tmin = 0.760, Tmax = 0.934l = 1414
2693 measured reflections3 standard reflections every 97 reflections
1886 independent reflections intensity decay: none
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0728P)2 + 0.2602P]
where P = (Fo2 + 2Fc2)/3
1886 reflections(Δ/σ)max < 0.001
155 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.17 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 > 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
C30.1199 (4)0.94896 (13)0.17007 (18)0.0525 (6)
H30.02550.94260.19470.063*
C40.2807 (4)0.99537 (13)0.23850 (17)0.0505 (6)
O10.2318 (3)0.88325 (11)0.03402 (13)0.0667 (5)
C10.0313 (4)0.87322 (13)0.01537 (17)0.0493 (5)
C20.1552 (4)0.91476 (14)0.07713 (18)0.0539 (6)
H20.29970.91700.05050.065*
C50.4907 (4)1.02167 (14)0.20585 (18)0.0552 (6)
H60.53731.00710.13900.066*
C100.0273 (4)0.81689 (13)0.07118 (17)0.0479 (5)
C110.1380 (4)0.79990 (14)0.15224 (18)0.0555 (6)
H110.27880.82560.15350.067*
C90.2204 (4)1.01738 (15)0.34040 (19)0.0605 (6)
H90.08141.00040.36450.073*
C60.6301 (4)1.06912 (14)0.27179 (19)0.0577 (6)
H100.76811.08700.24770.069*
C150.2365 (4)0.77845 (15)0.07075 (19)0.0590 (6)
H150.35030.79050.01830.071*
C80.3636 (4)1.06403 (16)0.4060 (2)0.0665 (7)
H120.31971.07760.47370.080*
C130.1107 (5)0.70628 (17)0.2283 (2)0.0710 (7)
H130.13850.66900.28090.085*
C70.5702 (4)1.09096 (14)0.37333 (19)0.0587 (6)
C160.7239 (5)1.14314 (19)0.4445 (2)0.0813 (9)
H16A0.88011.12730.43870.122*
H16B0.68401.13740.51720.122*
H16C0.70541.19790.42290.122*
C120.0952 (5)0.74546 (16)0.2305 (2)0.0673 (7)
H170.20590.73510.28500.081*
C140.2766 (4)0.72213 (16)0.1482 (2)0.0692 (7)
H140.41530.69500.14630.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C30.0479 (13)0.0516 (12)0.0582 (14)0.0019 (10)0.0049 (10)0.0015 (11)
C40.0497 (13)0.0504 (12)0.0511 (13)0.0050 (10)0.0004 (10)0.0008 (10)
O10.0472 (10)0.0825 (12)0.0711 (11)0.0002 (9)0.0088 (8)0.0152 (9)
C10.0433 (13)0.0518 (13)0.0532 (12)0.0020 (10)0.0063 (10)0.0031 (10)
C20.0487 (13)0.0566 (13)0.0564 (13)0.0016 (11)0.0049 (10)0.0025 (11)
C50.0533 (14)0.0574 (14)0.0552 (13)0.0030 (11)0.0066 (11)0.0044 (11)
C100.0431 (12)0.0495 (12)0.0514 (12)0.0044 (9)0.0064 (9)0.0035 (10)
C110.0497 (13)0.0544 (13)0.0622 (14)0.0007 (11)0.0011 (11)0.0007 (11)
C90.0539 (14)0.0708 (16)0.0573 (14)0.0003 (12)0.0079 (11)0.0041 (12)
C60.0522 (14)0.0562 (14)0.0644 (15)0.0020 (11)0.0024 (11)0.0017 (11)
C150.0472 (13)0.0665 (15)0.0632 (14)0.0006 (11)0.0021 (11)0.0043 (12)
C80.0614 (16)0.0824 (18)0.0559 (14)0.0082 (13)0.0048 (12)0.0139 (13)
C130.0732 (18)0.0684 (16)0.0726 (17)0.0027 (14)0.0155 (14)0.0160 (13)
C70.0570 (15)0.0562 (14)0.0618 (14)0.0093 (11)0.0057 (11)0.0083 (11)
C160.0792 (19)0.0809 (19)0.0824 (19)0.0037 (15)0.0071 (15)0.0217 (15)
C120.0676 (17)0.0714 (16)0.0620 (15)0.0060 (13)0.0023 (12)0.0115 (13)
C140.0573 (15)0.0674 (16)0.0838 (18)0.0063 (13)0.0111 (13)0.0089 (14)
Geometric parameters (Å, º) top
C1—C21.474 (3)C9—H90.9300
C1—C101.493 (3)C6—C71.390 (3)
C2—C31.326 (3)C6—H100.9300
C3—C41.459 (3)C15—C141.384 (3)
C3—H30.9300C15—H150.9300
C4—C51.392 (3)C8—C71.378 (3)
C4—C91.396 (3)C8—H120.9300
O1—C11.224 (2)C13—C121.372 (3)
C2—H20.9300C13—C141.379 (4)
C5—C61.378 (3)C13—H130.9300
C5—H60.9300C7—C161.507 (3)
C10—C151.384 (3)C16—H16A0.9600
C10—C111.389 (3)C16—H16B0.9600
C11—C121.373 (3)C16—H16C0.9600
C11—H110.9300C12—H170.9300
C9—C81.381 (3)C14—H140.9300
C2—C3—C4128.1 (2)C7—C6—H10119.1
C2—C3—H3116.0C14—C15—C10120.2 (2)
C4—C3—H3116.0C14—C15—H15119.9
C5—C4—C9117.7 (2)C10—C15—H15119.9
C5—C4—C3123.1 (2)C7—C8—C9121.4 (2)
C9—C4—C3119.2 (2)C7—C8—H12119.3
O1—C1—C2121.6 (2)C9—C8—H12119.3
O1—C1—C10119.5 (2)C12—C13—C14120.1 (2)
C2—C1—C10118.91 (18)C12—C13—H13119.9
C3—C2—C1121.0 (2)C14—C13—H13119.9
C3—C2—H2119.5C8—C7—C6117.5 (2)
C1—C2—H2119.5C8—C7—C16121.2 (2)
C6—C5—C4120.5 (2)C6—C7—C16121.3 (2)
C6—C5—H6119.7C7—C16—H16A109.5
C4—C5—H6119.7C7—C16—H16B109.5
C15—C10—C11119.0 (2)H16A—C16—H16B109.5
C15—C10—C1122.2 (2)C7—C16—H16C109.5
C11—C10—C1118.66 (19)H16A—C16—H16C109.5
C12—C11—C10120.6 (2)H16B—C16—H16C109.5
C12—C11—H11119.7C13—C12—C11120.1 (2)
C10—C11—H11119.7C13—C12—H17119.9
C8—C9—C4121.0 (2)C11—C12—H17119.9
C8—C9—H9119.5C13—C14—C15119.9 (2)
C4—C9—H9119.5C13—C14—H14120.0
C5—C6—C7121.8 (2)C15—C14—H14120.0
C5—C6—H10119.1
O1—C1—C2—C316.3 (3)C3—C4—C9—C8177.4 (2)
O1—C1—C10—C1123.2 (3)C4—C5—C6—C71.5 (4)
O1—C1—C10—C15153.9 (2)C11—C10—C15—C142.0 (3)
C2—C3—C4—C511.0 (4)C1—C10—C15—C14175.0 (2)
C2—C3—C4—C9171.4 (2)C4—C9—C8—C70.4 (4)
C2—C1—C10—C11157.5 (2)C9—C8—C7—C60.3 (4)
C2—C1—C10—C1525.4 (3)C9—C8—C7—C16178.8 (3)
C4—C3—C2—C1176.8 (2)C5—C6—C7—C80.6 (4)
C10—C1—C2—C3163.0 (2)C5—C6—C7—C16179.8 (2)
C9—C4—C5—C61.3 (3)C14—C13—C12—C110.8 (4)
C3—C4—C5—C6176.3 (2)C10—C11—C12—C131.0 (4)
C15—C10—C11—C120.4 (3)C12—C13—C14—C150.9 (4)
C1—C10—C11—C12176.8 (2)C10—C15—C14—C132.3 (4)
C5—C4—C9—C80.4 (4)
 

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