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The title compound, C23H22O3, has been synthesized by the reaction of furfural with 4-methyl­acetophenone and NaOH. The bond lengths and angles have normal values. The crystal packing exhibits no significantly short inter­molecular contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043789/ez2043sup1.cif
Contains datablocks I, 060811a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043789/ez2043Isup2.hkl
Contains datablock I

CCDC reference: 627645

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.065
  • wR factor = 0.273
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.273 RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.107 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 41 Perc. PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT084_ALERT_2_C High R2 Value .................................. 0.27 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

1,5-Bis(4-methylphenyl)-3-(2-furanyl)pentane-1,5-dione top
Crystal data top
C23H22O3F(000) = 736
Mr = 346.41Dx = 1.229 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 15.831 (7) ÅCell parameters from 1152 reflections
b = 11.575 (5) Åθ = 2.6–20.1°
c = 10.215 (4) ŵ = 0.08 mm1
β = 91.080 (7)°T = 298 K
V = 1871.5 (14) Å3Block, colorless
Z = 40.65 × 0.43 × 0.40 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
3258 independent reflections
Radiation source: fine-focus sealed tube1351 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.107
φ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1418
Tmin = 0.950, Tmax = 0.969k = 1313
9405 measured reflectionsl = 1112
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.273H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.080P)2]
where P = (Fo2 + 2Fc2)/3
3258 reflections(Δ/σ)max < 0.001
235 parametersΔρmax = 0.19 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
O10.2556 (2)0.5681 (3)0.1274 (3)0.0797 (11)
O20.17042 (18)0.9163 (3)0.0746 (3)0.0704 (10)
O30.41237 (19)0.8360 (3)0.1275 (3)0.0651 (9)
C10.2913 (4)0.4636 (5)0.1586 (6)0.0847 (17)
H10.26780.40910.21550.102*
C20.3640 (4)0.4529 (5)0.0949 (6)0.0863 (17)
H20.40080.39030.09900.104*
C30.3759 (3)0.5541 (4)0.0190 (6)0.0791 (16)
H30.42210.57070.03540.095*
C40.3090 (3)0.6209 (4)0.0399 (4)0.0563 (12)
C50.2809 (2)0.7350 (3)0.0105 (4)0.0520 (11)
H50.26230.78260.06390.062*
C60.2065 (2)0.7190 (3)0.1015 (4)0.0572 (12)
H6A0.16820.66290.06230.069*
H6B0.22760.68650.18330.069*
C70.1570 (2)0.8266 (4)0.1319 (4)0.0525 (11)
C80.0893 (2)0.8191 (4)0.2302 (4)0.0546 (12)
C90.0717 (3)0.7207 (4)0.2996 (5)0.0619 (13)
H90.10300.65410.28480.074*
C100.0086 (3)0.7184 (4)0.3910 (5)0.0704 (14)
H100.00240.65040.43610.084*
C110.0383 (3)0.8160 (5)0.4161 (5)0.0726 (14)
C120.0200 (3)0.9131 (5)0.3488 (6)0.0855 (17)
H120.05090.97970.36490.103*
C130.0426 (3)0.9171 (4)0.2576 (5)0.0746 (15)
H130.05370.98580.21410.090*
C140.1074 (3)0.8132 (5)0.5184 (6)0.107 (2)
H14A0.13090.88920.52770.161*
H14B0.08370.78830.60080.161*
H14C0.15110.76050.49080.161*
C150.3543 (2)0.7954 (4)0.0797 (4)0.0551 (12)
H15A0.33350.86500.12120.066*
H15B0.37660.74520.14800.066*
C160.4247 (3)0.8275 (3)0.0103 (5)0.0507 (11)
C170.5105 (3)0.8475 (3)0.0483 (4)0.0505 (11)
C180.5263 (3)0.8454 (4)0.1814 (5)0.0623 (13)
H180.48250.83010.23820.075*
C190.6058 (3)0.8656 (4)0.2305 (5)0.0696 (14)
H190.61520.86280.32060.084*
C200.6726 (3)0.8901 (4)0.1500 (5)0.0623 (13)
C210.6571 (3)0.8919 (4)0.0184 (5)0.0658 (13)
H210.70140.90660.03770.079*
C220.5774 (3)0.8724 (4)0.0340 (4)0.0608 (13)
H220.56820.87590.12410.073*
C230.7597 (3)0.9127 (5)0.2069 (6)0.0933 (18)
H23A0.79320.84380.20120.140*
H23B0.75530.93510.29700.140*
H23C0.78610.97360.15870.140*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.078 (2)0.090 (2)0.071 (3)0.0076 (19)0.0126 (19)0.0235 (19)
O20.070 (2)0.062 (2)0.080 (3)0.0060 (16)0.0071 (18)0.0120 (18)
O30.078 (2)0.076 (2)0.041 (2)0.0014 (16)0.0002 (16)0.0028 (16)
C10.106 (5)0.075 (4)0.074 (4)0.006 (3)0.014 (4)0.019 (3)
C20.095 (4)0.072 (4)0.093 (5)0.015 (3)0.008 (4)0.005 (3)
C30.071 (3)0.065 (3)0.100 (4)0.017 (3)0.022 (3)0.007 (3)
C40.059 (3)0.062 (3)0.047 (3)0.002 (2)0.001 (2)0.003 (2)
C50.052 (3)0.057 (3)0.047 (3)0.009 (2)0.007 (2)0.002 (2)
C60.052 (3)0.061 (3)0.059 (3)0.003 (2)0.003 (2)0.001 (2)
C70.048 (3)0.055 (3)0.055 (3)0.001 (2)0.008 (2)0.000 (2)
C80.042 (3)0.065 (3)0.056 (3)0.003 (2)0.010 (2)0.004 (2)
C90.062 (3)0.061 (3)0.062 (3)0.001 (2)0.002 (3)0.000 (3)
C100.064 (3)0.084 (4)0.063 (4)0.017 (3)0.000 (3)0.002 (3)
C110.046 (3)0.107 (4)0.065 (4)0.002 (3)0.000 (2)0.000 (3)
C120.071 (4)0.097 (4)0.089 (5)0.030 (3)0.008 (3)0.004 (3)
C130.068 (3)0.068 (3)0.088 (4)0.013 (2)0.014 (3)0.010 (3)
C140.069 (4)0.159 (6)0.095 (5)0.004 (4)0.024 (3)0.005 (4)
C150.057 (3)0.067 (3)0.041 (3)0.003 (2)0.003 (2)0.002 (2)
C160.066 (3)0.045 (2)0.041 (3)0.001 (2)0.006 (2)0.002 (2)
C170.063 (3)0.043 (2)0.046 (3)0.0014 (19)0.001 (2)0.003 (2)
C180.063 (3)0.077 (3)0.047 (3)0.009 (2)0.004 (2)0.000 (2)
C190.075 (4)0.080 (3)0.053 (3)0.017 (3)0.013 (3)0.002 (3)
C200.060 (3)0.056 (3)0.071 (4)0.003 (2)0.001 (3)0.005 (2)
C210.062 (3)0.070 (3)0.066 (4)0.005 (2)0.009 (3)0.004 (3)
C220.074 (4)0.065 (3)0.044 (3)0.002 (2)0.008 (3)0.002 (2)
C230.072 (4)0.100 (4)0.107 (5)0.018 (3)0.013 (3)0.019 (3)
Geometric parameters (Å, º) top
O1—C41.363 (5)C11—C141.527 (7)
O1—C11.376 (6)C12—C131.373 (7)
O2—C71.212 (5)C12—H120.9300
O3—C161.213 (5)C13—H130.9300
C1—C21.318 (7)C14—H14A0.9600
C1—H10.9300C14—H14B0.9600
C2—C31.416 (7)C14—H14C0.9600
C2—H20.9300C15—C161.505 (5)
C3—C41.325 (6)C15—H15A0.9700
C3—H30.9300C15—H15B0.9700
C4—C51.489 (6)C16—C171.492 (6)
C5—C151.519 (5)C17—C181.378 (6)
C5—C61.525 (5)C17—C221.393 (6)
C5—H50.9800C18—C191.366 (6)
C6—C71.507 (6)C18—H180.9300
C6—H6A0.9700C19—C201.381 (6)
C6—H6B0.9700C19—H190.9300
C7—C81.484 (6)C20—C211.362 (7)
C8—C91.373 (6)C20—C231.508 (7)
C8—C131.385 (6)C21—C221.380 (6)
C9—C101.381 (6)C21—H210.9300
C9—H90.9300C22—H220.9300
C10—C111.377 (7)C23—H23A0.9600
C10—H100.9300C23—H23B0.9600
C11—C121.352 (7)C23—H23C0.9600
C4—O1—C1107.1 (4)C12—C13—C8120.3 (5)
C2—C1—O1109.1 (5)C12—C13—H13119.8
C2—C1—H1125.5C8—C13—H13119.8
O1—C1—H1125.5C11—C14—H14A109.5
C1—C2—C3107.4 (5)C11—C14—H14B109.5
C1—C2—H2126.3H14A—C14—H14B109.5
C3—C2—H2126.3C11—C14—H14C109.5
C4—C3—C2107.3 (5)H14A—C14—H14C109.5
C4—C3—H3126.4H14B—C14—H14C109.5
C2—C3—H3126.4C16—C15—C5113.5 (4)
C3—C4—O1109.2 (4)C16—C15—H15A108.9
C3—C4—C5134.8 (5)C5—C15—H15A108.9
O1—C4—C5116.0 (4)C16—C15—H15B108.9
C4—C5—C15109.8 (4)C5—C15—H15B108.9
C4—C5—C6110.0 (3)H15A—C15—H15B107.7
C15—C5—C6111.4 (3)O3—C16—C17120.7 (4)
C4—C5—H5108.5O3—C16—C15121.0 (4)
C15—C5—H5108.5C17—C16—C15118.2 (4)
C6—C5—H5108.5C18—C17—C22118.2 (4)
C7—C6—C5115.8 (4)C18—C17—C16122.7 (4)
C7—C6—H6A108.3C22—C17—C16119.1 (4)
C5—C6—H6A108.3C19—C18—C17120.5 (4)
C7—C6—H6B108.3C19—C18—H18119.7
C5—C6—H6B108.3C17—C18—H18119.7
H6A—C6—H6B107.4C18—C19—C20121.8 (5)
O2—C7—C8120.8 (4)C18—C19—H19119.1
O2—C7—C6120.8 (4)C20—C19—H19119.1
C8—C7—C6118.4 (4)C21—C20—C19117.7 (5)
C9—C8—C13117.4 (5)C21—C20—C23121.6 (5)
C9—C8—C7123.7 (4)C19—C20—C23120.7 (5)
C13—C8—C7118.9 (4)C20—C21—C22121.8 (4)
C8—C9—C10121.4 (4)C20—C21—H21119.1
C8—C9—H9119.3C22—C21—H21119.1
C10—C9—H9119.3C21—C22—C17119.9 (4)
C11—C10—C9120.6 (5)C21—C22—H22120.0
C11—C10—H10119.7C17—C22—H22120.0
C9—C10—H10119.7C20—C23—H23A109.5
C12—C11—C10117.8 (5)C20—C23—H23B109.5
C12—C11—C14121.9 (5)H23A—C23—H23B109.5
C10—C11—C14120.4 (5)C20—C23—H23C109.5
C11—C12—C13122.5 (5)H23A—C23—H23C109.5
C11—C12—H12118.8H23B—C23—H23C109.5
C13—C12—H12118.8
 

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