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The title compound, C35H28O4, is a tetrasubstituted 4H-pyran-4-one with 2,6-bis(p-tolyl) and 3,5-bis(p-toluyl) substituents. The pyran ring is almost planar; the planes of the toluyl substituents are approximately orthogonal to the pyran mean plane [both dihedral angles are equal to 86.2 (1)°], whereas the tolyl planes form with the latter much smaller dihedral angles of 32.5 (1) and 47.2 (1)°. The crystal structure features two intramolecular C—H...O contacts and a C—H...π(ring) interaction, with an H...Cg distance of 2.70 (3) Å (Cg is the centroid of one of the benzene rings).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804000121/ya6191sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804000121/ya6191Isup2.hkl
Contains datablock I

CCDC reference: 234868

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.045
  • wR factor = 0.090
  • Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O1 .. O2 = 2.82 Ang.
Alert level C ABSMU01_ALERT_1_C The ratio of given/expected absorption coefficient lies outside the range 0.99 <> 1.01 Calculated value of mu = 0.081 Value of mu given = 0.080 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 44 Perc. PLAT230_ALERT_2_C Hirshfeld Test Diff for C25 - C26 = 5.03 su PLAT351_ALERT_3_C Long C-H Bond (0.96A) C27 - H27 = 1.11 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 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 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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).

3,5-Bis(4-methylbenzoyl)-2,6-bis(4-methylphenyl)-4H-pyran-4-one top
Crystal data top
C35H28O4F(000) = 1080
Mr = 512.57Dx = 1.251 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7653 reflections
a = 10.8893 (10) Åθ = 1.7–24.1°
b = 10.6093 (7) ŵ = 0.08 mm1
c = 23.629 (2) ÅT = 293 K
β = 94.297 (7)°Prism, yellow
V = 2722.1 (4) Å30.32 × 0.26 × 0.13 mm
Z = 4
Data collection top
Stoe IPDS-2
diffractometer
2115 reflections with I > 2σ(I)
Radiation source: sealed X-ray tubeRint = 0.085
Plane graphite monochromatorθmax = 25.0°, θmin = 1.7°
Detector resolution: 6.67 pixels mm-1h = 1112
φ scansk = 1212
24172 measured reflectionsl = 2828
4785 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090 w = 1/[σ2(Fo2) + (0.0246P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
4785 reflectionsΔρmax = 0.17 e Å3
417 parametersΔρmin = 0.16 e Å3
105 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0137 (7)
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
O10.40957 (14)0.33407 (14)0.22917 (6)0.0586 (4)
O20.09072 (17)0.10024 (18)0.27285 (7)0.0892 (6)
O30.08728 (16)0.23371 (18)0.14560 (7)0.0854 (6)
O40.24416 (17)0.37582 (18)0.04744 (7)0.0891 (6)
C10.3148 (2)0.2915 (2)0.25881 (9)0.0573 (6)
C20.2056 (2)0.2600 (2)0.23252 (9)0.0590 (6)
C30.1865 (3)0.2647 (2)0.17114 (10)0.0659 (7)
C40.2922 (2)0.3051 (2)0.14178 (9)0.0579 (6)
C50.3964 (2)0.3416 (2)0.17073 (9)0.0570 (6)
C60.2788 (2)0.2895 (3)0.07851 (10)0.0665 (7)
C70.3060 (2)0.1625 (3)0.05648 (10)0.0620 (7)
C80.2890 (3)0.1387 (3)0.00136 (11)0.0784 (8)
H80.257 (2)0.211 (2)0.0265 (10)0.102 (9)*
C90.3146 (3)0.0199 (4)0.02181 (14)0.0880 (9)
H90.302 (2)0.007 (2)0.0636 (11)0.101 (9)*
C100.3556 (2)0.0765 (3)0.01344 (13)0.0806 (8)
C110.3727 (3)0.0524 (3)0.07046 (13)0.0809 (8)
H110.403 (2)0.119 (2)0.0958 (10)0.098 (10)*
C120.3477 (2)0.0658 (3)0.09199 (12)0.0731 (8)
H120.357 (2)0.081 (2)0.1309 (9)0.083 (8)*
C130.5112 (2)0.3881 (2)0.14893 (9)0.0557 (6)
C140.5112 (3)0.4619 (2)0.10022 (10)0.0659 (7)
H140.427 (2)0.477 (2)0.0816 (9)0.087 (8)*
C150.6203 (3)0.5033 (3)0.08109 (11)0.0704 (8)
H150.619 (2)0.557 (2)0.0451 (10)0.112 (10)*
C160.7324 (2)0.4745 (2)0.10890 (10)0.0677 (7)
C170.7321 (3)0.4015 (3)0.15753 (11)0.0750 (8)
H170.811 (2)0.379 (2)0.1776 (9)0.096 (9)*
C180.6237 (3)0.3610 (3)0.17761 (11)0.0672 (7)
H180.623 (2)0.314 (2)0.2129 (9)0.080 (8)*
C190.3511 (2)0.2889 (2)0.32022 (9)0.0589 (6)
C200.3274 (3)0.1853 (3)0.35341 (11)0.0712 (8)
H200.287 (2)0.115 (2)0.3389 (9)0.076 (8)*
C210.3625 (3)0.1846 (3)0.41091 (11)0.0729 (8)
H210.345 (2)0.112 (2)0.4316 (10)0.098 (10)*
C220.4218 (2)0.2866 (3)0.43656 (10)0.0697 (7)
C230.4441 (3)0.3887 (3)0.40326 (11)0.0759 (8)
H230.483 (2)0.458 (2)0.4198 (9)0.087 (9)*
C240.4108 (2)0.3914 (3)0.34582 (11)0.0676 (7)
H240.4260 (19)0.465 (2)0.3232 (8)0.067 (7)*
C250.0996 (2)0.2130 (3)0.26356 (9)0.0661 (7)
C260.0051 (2)0.3031 (2)0.27984 (9)0.0608 (6)
C270.0958 (3)0.2577 (3)0.30712 (10)0.0723 (7)
H270.095 (3)0.158 (3)0.3214 (10)0.131 (11)*
C280.1881 (3)0.3399 (3)0.32006 (11)0.0762 (8)
H280.263 (2)0.306 (2)0.3394 (10)0.101 (9)*
C290.1839 (3)0.4665 (3)0.30617 (10)0.0733 (7)
C300.0824 (3)0.5098 (3)0.28016 (12)0.0808 (9)
H300.071 (2)0.592 (3)0.2728 (10)0.103 (11)*
C310.0117 (3)0.4298 (3)0.26730 (11)0.0705 (8)
H310.079 (2)0.462 (2)0.2488 (8)0.068 (8)*
C320.2887 (3)0.5526 (3)0.31761 (12)0.1001 (9)
H32A0.35040.50590.33570.150*
H32B0.32390.58670.28240.150*
H32C0.25890.62000.34200.150*
C330.4598 (3)0.2848 (3)0.49934 (9)0.0982 (10)
H33A0.49930.36300.51010.147*
H33B0.51590.21630.50760.147*
H33C0.38820.27390.52020.147*
C340.8532 (2)0.5203 (3)0.08873 (10)0.0957 (9)
H34A0.92000.48970.11380.144*
H34B0.85410.61080.08850.144*
H34C0.86200.48950.05110.144*
C350.3823 (3)0.2056 (3)0.01013 (13)0.1124 (11)
H35A0.40960.26090.02040.169*
H35B0.44540.19870.03620.169*
H35C0.30880.23910.02950.169*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0639 (11)0.0618 (11)0.0505 (9)0.0077 (9)0.0069 (8)0.0040 (7)
O20.0966 (15)0.0606 (13)0.1139 (14)0.0065 (11)0.0311 (11)0.0077 (11)
O30.0704 (12)0.1130 (16)0.0720 (11)0.0184 (11)0.0006 (9)0.0032 (10)
O40.1149 (16)0.0807 (14)0.0689 (11)0.0014 (12)0.0112 (10)0.0072 (10)
C10.0660 (17)0.0501 (15)0.0569 (14)0.0065 (13)0.0116 (13)0.0009 (11)
C20.0642 (16)0.0588 (16)0.0551 (14)0.0068 (13)0.0106 (12)0.0022 (12)
C30.0713 (18)0.0638 (18)0.0622 (16)0.0035 (15)0.0027 (14)0.0037 (13)
C40.0636 (17)0.0578 (16)0.0524 (14)0.0039 (13)0.0042 (12)0.0025 (12)
C50.0702 (17)0.0521 (16)0.0493 (14)0.0004 (13)0.0077 (12)0.0015 (11)
C60.0645 (18)0.0750 (19)0.0592 (16)0.0075 (15)0.0007 (13)0.0042 (14)
C70.0589 (17)0.0740 (18)0.0535 (15)0.0088 (14)0.0062 (12)0.0055 (13)
C80.078 (2)0.099 (2)0.0574 (17)0.0008 (19)0.0033 (14)0.0081 (17)
C90.081 (2)0.116 (3)0.067 (2)0.006 (2)0.0092 (16)0.028 (2)
C100.0658 (19)0.089 (2)0.089 (2)0.0058 (17)0.0150 (16)0.0261 (18)
C110.081 (2)0.081 (2)0.082 (2)0.0043 (18)0.0127 (16)0.0100 (19)
C120.082 (2)0.076 (2)0.0617 (18)0.0024 (16)0.0089 (15)0.0071 (15)
C130.0606 (16)0.0538 (16)0.0529 (14)0.0013 (13)0.0064 (12)0.0038 (12)
C140.0692 (19)0.0701 (19)0.0589 (15)0.0045 (16)0.0072 (14)0.0015 (13)
C150.077 (2)0.074 (2)0.0619 (16)0.0060 (16)0.0098 (15)0.0079 (14)
C160.0686 (18)0.0692 (18)0.0665 (15)0.0115 (15)0.0140 (14)0.0027 (14)
C170.0647 (19)0.085 (2)0.0754 (18)0.0089 (17)0.0029 (16)0.0081 (15)
C180.0671 (19)0.071 (2)0.0633 (17)0.0078 (15)0.0050 (14)0.0072 (14)
C190.0616 (16)0.0604 (17)0.0551 (14)0.0025 (14)0.0074 (11)0.0012 (13)
C200.084 (2)0.063 (2)0.0675 (18)0.0074 (16)0.0093 (15)0.0018 (15)
C210.077 (2)0.079 (2)0.0631 (18)0.0044 (17)0.0086 (14)0.0124 (16)
C220.0605 (17)0.093 (2)0.0562 (15)0.0024 (16)0.0071 (13)0.0034 (15)
C230.078 (2)0.086 (2)0.0637 (18)0.0109 (18)0.0041 (14)0.0117 (16)
C240.0743 (19)0.0697 (19)0.0591 (17)0.0106 (16)0.0077 (13)0.0000 (15)
C250.0749 (19)0.0652 (19)0.0580 (15)0.0120 (16)0.0044 (13)0.0014 (14)
C260.0616 (16)0.0633 (18)0.0577 (14)0.0081 (15)0.0067 (12)0.0007 (13)
C270.0742 (19)0.079 (2)0.0642 (16)0.0081 (18)0.0096 (14)0.0061 (15)
C280.069 (2)0.085 (2)0.0761 (18)0.0082 (18)0.0155 (16)0.0057 (16)
C290.0681 (19)0.083 (2)0.0686 (16)0.0012 (18)0.0033 (14)0.0021 (15)
C300.080 (2)0.069 (2)0.095 (2)0.0047 (19)0.0156 (16)0.0036 (17)
C310.0691 (19)0.066 (2)0.0775 (18)0.0099 (17)0.0154 (15)0.0006 (15)
C320.080 (2)0.107 (2)0.115 (2)0.0169 (19)0.0184 (17)0.0044 (19)
C330.085 (2)0.150 (3)0.0581 (15)0.007 (2)0.0040 (14)0.0016 (16)
C340.083 (2)0.114 (3)0.0929 (19)0.0230 (19)0.0252 (16)0.0101 (17)
C350.095 (2)0.105 (3)0.142 (3)0.007 (2)0.0353 (19)0.050 (2)
Geometric parameters (Å, º) top
O1—C11.367 (3)C19—C241.382 (3)
O1—C51.380 (2)C19—C201.386 (3)
O2—C251.221 (3)C20—C211.384 (3)
O3—C31.242 (2)C20—H200.92 (2)
O4—C61.216 (3)C21—C221.377 (3)
C1—C21.342 (3)C21—H210.94 (2)
C1—C191.475 (3)C22—C231.371 (4)
C2—C31.451 (3)C22—C331.510 (3)
C2—C251.498 (3)C23—C241.379 (3)
C3—C41.452 (3)C23—H230.92 (2)
C4—C51.338 (3)C24—H240.97 (2)
C4—C61.500 (3)C25—C261.477 (3)
C5—C131.472 (3)C26—C311.379 (3)
C6—C71.483 (3)C26—C271.400 (3)
C7—C121.381 (3)C27—C281.382 (4)
C7—C81.388 (3)C27—H271.11 (3)
C8—C91.386 (4)C28—C291.384 (4)
C8—H81.02 (2)C28—H281.03 (3)
C9—C101.372 (4)C29—C301.382 (4)
C9—H91.00 (2)C29—C321.503 (3)
C10—C111.370 (4)C30—C311.382 (4)
C10—C351.515 (4)C30—H300.90 (3)
C11—C121.387 (4)C31—H310.95 (2)
C11—H110.97 (2)C32—H32A0.9600
C12—H120.93 (2)C32—H32B0.9600
C13—C181.385 (3)C32—H32C0.9600
C13—C141.392 (3)C33—H33A0.9600
C14—C151.374 (3)C33—H33B0.9600
C14—H141.00 (2)C33—H33C0.9600
C15—C161.377 (3)C34—H34A0.9600
C15—H151.02 (3)C34—H34B0.9600
C16—C171.386 (3)C34—H34C0.9600
C16—C341.512 (3)C35—H35A0.9600
C17—C181.373 (3)C35—H35B0.9600
C17—H170.98 (2)C35—H35C0.9600
C18—H180.97 (2)
C1—O1—C5120.41 (18)C21—C20—H20116.8 (14)
C2—C1—O1121.5 (2)C19—C20—H20122.5 (14)
C2—C1—C19127.9 (2)C22—C21—C20120.9 (3)
O1—C1—C19110.6 (2)C22—C21—H21121.7 (15)
C1—C2—C3120.7 (2)C20—C21—H21117.4 (15)
C1—C2—C25123.0 (2)C23—C22—C21117.7 (3)
C3—C2—C25116.3 (2)C23—C22—C33121.8 (3)
O3—C3—C2122.1 (2)C21—C22—C33120.5 (3)
O3—C3—C4122.5 (2)C22—C23—C24122.4 (3)
C2—C3—C4115.4 (2)C22—C23—H23119.0 (15)
C5—C4—C3120.9 (2)C24—C23—H23118.6 (15)
C5—C4—C6123.8 (2)C23—C24—C19119.7 (3)
C3—C4—C6115.0 (2)C23—C24—H24121.1 (12)
C4—C5—O1121.0 (2)C19—C24—H24119.2 (12)
C4—C5—C13128.9 (2)O2—C25—C26121.4 (3)
O1—C5—C13110.04 (19)O2—C25—C2119.2 (3)
O4—C6—C7122.3 (2)C26—C25—C2119.3 (2)
O4—C6—C4121.4 (2)C31—C26—C27119.3 (3)
C7—C6—C4116.3 (2)C31—C26—C25121.7 (3)
C12—C7—C8118.5 (3)C27—C26—C25118.9 (3)
C12—C7—C6121.8 (2)C28—C27—C26119.5 (3)
C8—C7—C6119.7 (3)C28—C27—H27121.6 (15)
C9—C8—C7119.5 (3)C26—C27—H27118.7 (15)
C9—C8—H8123.6 (14)C27—C28—C29121.5 (3)
C7—C8—H8116.9 (14)C27—C28—H28119.3 (15)
C10—C9—C8122.1 (3)C29—C28—H28119.2 (15)
C10—C9—H9121.0 (15)C30—C29—C28118.1 (3)
C8—C9—H9116.9 (15)C30—C29—C32121.4 (3)
C11—C10—C9118.1 (3)C28—C29—C32120.5 (3)
C11—C10—C35121.0 (3)C31—C30—C29121.6 (3)
C9—C10—C35120.9 (3)C31—C30—H30116.1 (19)
C10—C11—C12120.9 (3)C29—C30—H30122.2 (19)
C10—C11—H11119.1 (15)C26—C31—C30120.0 (3)
C12—C11—H11120.0 (15)C26—C31—H31120.3 (14)
C7—C12—C11120.9 (3)C30—C31—H31119.7 (14)
C7—C12—H12118.3 (15)C29—C32—H32A109.5
C11—C12—H12120.9 (15)C29—C32—H32B109.5
C18—C13—C14117.8 (2)H32A—C32—H32B109.5
C18—C13—C5120.1 (2)C29—C32—H32C109.5
C14—C13—C5122.0 (2)H32A—C32—H32C109.5
C15—C14—C13120.3 (3)H32B—C32—H32C109.5
C15—C14—H14126.0 (14)C22—C33—H33A109.5
C13—C14—H14113.6 (14)C22—C33—H33B109.5
C14—C15—C16122.0 (3)H33A—C33—H33B109.5
C14—C15—H15119.3 (15)C22—C33—H33C109.5
C16—C15—H15118.7 (15)H33A—C33—H33C109.5
C15—C16—C17117.6 (3)H33B—C33—H33C109.5
C15—C16—C34122.6 (2)C16—C34—H34A109.5
C17—C16—C34119.8 (3)C16—C34—H34B109.5
C18—C17—C16121.1 (3)H34A—C34—H34B109.5
C18—C17—H17120.2 (14)C16—C34—H34C109.5
C16—C17—H17118.7 (15)H34A—C34—H34C109.5
C17—C18—C13121.1 (3)H34B—C34—H34C109.5
C17—C18—H18121.4 (14)C10—C35—H35A109.5
C13—C18—H18117.4 (14)C10—C35—H35B109.5
C24—C19—C20118.5 (2)H35A—C35—H35B109.5
C24—C19—C1119.9 (2)C10—C35—H35C109.5
C20—C19—C1121.6 (2)H35A—C35—H35C109.5
C21—C20—C19120.7 (3)H35B—C35—H35C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O41.00 (2)2.36 (2)3.210 (3)143.2 (19)
C20—H20···O20.92 (2)2.56 (2)3.216 (4)129.1 (18)
C27—H27···Cg3i1.11 (3)2.70 (3)3.792 (3)169 (2)
Symmetry code: (i) x+1/2, y1/2, z+1/2.
 

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