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Acta Crystallogr Sect E Struct Rep Online. 2012 September 1; 68(Pt 9): o2820.
Published online 2012 August 31. doi:  10.1107/S1600536812036847
PMCID: PMC3435844

3-(9H-Fluoren-9-yl)-3-(4-methyl­phen­yl)-1-phenyl­propan-1-one

Abstract

In the title compound, C29H24O, the phenyl and methyl­phenyl rings are approximately perpendicular to each other, making a dihedral angle of 87.67 (10)°, and are oriented at dihedral angles of 62.49 (9) and 84.77 (7)°, respectively, to the nearly planar fluorene ring system [maximum deviation = 0.077 (2) Å] In the crystal, weak C—H(...)π inter­actions are observed.

Related literature  

For the background to fluorene and its derivatives, see: Kreyenschmidt et al. (1998 [triangle]).

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Object name is e-68-o2820-scheme1.jpg

Experimental  

Crystal data  

  • C29H24O
  • M r = 388.48
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-68-o2820-efi1.jpg
  • a = 9.7188 (16) Å
  • b = 10.8189 (18) Å
  • c = 11.5132 (19) Å
  • α = 75.500 (3)°
  • β = 68.681 (3)°
  • γ = 84.315 (3)°
  • V = 1091.8 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 298 K
  • 0.26 × 0.20 × 0.10 mm

Data collection  

  • Bruker SMART 1000 CCD area-detector diffractometer
  • 11991 measured reflections
  • 4508 independent reflections
  • 3125 reflections with I > 2σ(I)
  • R int = 0.022

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.138
  • S = 1.07
  • 4508 reflections
  • 272 parameters
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812036847/xu5614sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036847/xu5614Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812036847/xu5614Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors acknowledge financial support from the Project of Hubei Provincial Department of Education, China (No. D20122903).

supplementary crystallographic information

Comment

Since the publication of its solid-state structure of fluorene and its derivatives are very useful compounds due to their good optical property and high luminescent efficiencies, and have received a lot of attentiont (Kreyenschmidt et al., 1998). To our knowledge, a great number of studies have appeared on fluorene and its derivatives. The title compound (I) is an example of this class.

In the title compound, the phenyl ring and methylphenyl ring are approximately perpendicular to each other with a dihedral angle of 87.67 (10)°, and they are oriented with respect to the nearly planar fluorene ring systems [the maximum deviation being 0.077 (2) Å] at 62.49 (9) and 84.77 (7)°, respectively. In the crystal, weak intermolecular C—H···π interaction is observed (Table 1).

Experimental

Fluorene (2 mmo1), chalcone (2 mmo1) and NaOH (4 mmo1) were mixed in mortar, and the mixture was ground at room temperature for 30 min. Then, the mixture was washed in sequence with 15 ml aqueous solution of HCl (3%) and alcohol (95%), and the crude product was isolated by filtration. The filtrate was purified by recrystallization from anhydrous ethanol to give compound I as colourless crystals in 73% yield. Suitable crystals for X-ray analysis were obtained by slow evaporation of a methanol solution at room temperature (m.p. 445–447 K); IR (KBr, ν cm-1): 3055, 3010, 2915, 1680, 1596, 1445, 1316, 1238, 813, 685; 1H NMR (DMSO-d6, δ): 6.83–8.07 (m, 17H); 3.97 (d, 1H, J = 4.2 Hz), 3.57 (m, 1H), 3.41 (d, 2H, J = 7.0 Hz), 2.19 (s, 3H); Elemental analysis calculated for C29H24O: C 86.69, H6.19%; found: C 86.81, H 6.12%.

Refinement

All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93 Å for phenyl H atoms, C—H = 0.96 Å for methyl H atoms, C—H = 0.97 Å for methylene H atoms, C—H = 0.98 Å for methylidyne H atoms and Uiso(H) = 1.5Ueq(C).

Figures

Fig. 1.
The molecular structure of (I), showing 50% probability displacement ellipsoids.

Crystal data

C29H24OZ = 2
Mr = 388.48F(000) = 412
Triclinic, P1Dx = 1.182 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.7188 (16) ÅCell parameters from 2741 reflections
b = 10.8189 (18) Åθ = 2.3–24.1°
c = 11.5132 (19) ŵ = 0.07 mm1
α = 75.500 (3)°T = 298 K
β = 68.681 (3)°Block, colourless
γ = 84.315 (3)°0.26 × 0.20 × 0.10 mm
V = 1091.8 (3) Å3

Data collection

Bruker SMART 1000 CCD area-detector diffractometer3125 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 26.5°, θmin = 1.9°
phi and ω scansh = −12→12
11991 measured reflectionsk = −13→13
4508 independent reflectionsl = −14→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0713P)2 + 0.0224P] where P = (Fo2 + 2Fc2)/3
4508 reflections(Δ/σ)max < 0.001
272 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = −0.14 e Å3

Special details

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)

xyzUiso*/Ueq
C10.7361 (3)−0.3823 (3)0.2434 (4)0.1697 (14)
H1A0.6724−0.44710.24790.255*
H1B0.7775−0.41040.30980.255*
H1C0.8142−0.36650.16130.255*
C20.6470 (3)−0.2591 (2)0.2611 (4)0.1069 (8)
C30.6537 (2)−0.1587 (2)0.1586 (3)0.0959 (7)
H30.7134−0.16580.07650.115*
C40.57379 (17)−0.04748 (18)0.17503 (17)0.0716 (5)
H40.58050.01850.10370.086*
C50.48412 (15)−0.03221 (14)0.29525 (15)0.0550 (4)
C60.47896 (19)−0.13296 (16)0.39899 (18)0.0721 (5)
H60.4213−0.12550.48150.086*
C70.5588 (3)−0.24457 (19)0.3811 (3)0.0993 (7)
H70.5526−0.31110.45190.119*
C80.38850 (14)0.08493 (13)0.31928 (13)0.0487 (3)
H80.41070.11380.38470.058*
C90.22214 (14)0.05094 (13)0.37594 (12)0.0483 (3)
H90.2076−0.02180.44970.058*
C100.12098 (15)0.15808 (13)0.42180 (13)0.0510 (4)
C110.12221 (18)0.22548 (15)0.50885 (14)0.0651 (4)
H110.19450.20960.54600.078*
C120.0134 (2)0.31740 (17)0.53970 (17)0.0785 (5)
H120.01280.36360.59800.094*
C13−0.0940 (2)0.34070 (16)0.48454 (19)0.0795 (6)
H13−0.16600.40260.50630.095*
C14−0.09647 (17)0.27467 (15)0.39865 (17)0.0693 (5)
H14−0.16930.29120.36200.083*
C150.01168 (15)0.18229 (13)0.36693 (14)0.0543 (4)
C160.03253 (15)0.09317 (14)0.28503 (13)0.0544 (4)
C170.15716 (14)0.01666 (13)0.28738 (13)0.0498 (3)
C180.19680 (16)−0.07957 (15)0.22107 (15)0.0618 (4)
H180.2802−0.12980.22100.074*
C190.1106 (2)−0.09985 (19)0.15508 (17)0.0777 (5)
H190.1366−0.16390.10990.093*
C20−0.0136 (2)−0.0261 (2)0.15556 (17)0.0827 (6)
H20−0.0713−0.04230.11200.099*
C21−0.05361 (18)0.07084 (18)0.21919 (16)0.0729 (5)
H21−0.13700.12070.21820.087*
C220.41980 (15)0.19632 (14)0.20298 (13)0.0547 (4)
H22A0.42400.16510.12980.066*
H22B0.33860.25710.21860.066*
C230.56189 (15)0.26443 (13)0.17041 (14)0.0538 (4)
C240.63527 (15)0.34181 (13)0.03808 (14)0.0538 (4)
C250.76455 (17)0.40522 (16)0.01130 (17)0.0735 (5)
H250.80400.39760.07530.088*
C260.8347 (2)0.47915 (18)−0.1090 (2)0.0910 (6)
H260.92100.5215−0.12570.109*
C270.7787 (2)0.49087 (17)−0.2040 (2)0.0899 (7)
H270.82690.5410−0.28510.108*
C280.6513 (2)0.42882 (18)−0.18013 (17)0.0857 (6)
H280.61330.4362−0.24500.103*
C290.57968 (18)0.35505 (15)−0.05867 (15)0.0679 (4)
H290.49270.3138−0.04230.081*
O10.61395 (13)0.25998 (12)0.25284 (11)0.0812 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.148 (3)0.126 (2)0.296 (4)0.073 (2)−0.124 (3)−0.114 (3)
C20.0798 (15)0.0880 (16)0.192 (3)0.0286 (12)−0.0758 (18)−0.0689 (18)
C30.0586 (11)0.1152 (18)0.139 (2)0.0149 (12)−0.0379 (12)−0.0747 (16)
C40.0486 (9)0.0858 (12)0.0836 (12)−0.0001 (8)−0.0194 (8)−0.0312 (10)
C50.0415 (7)0.0599 (9)0.0671 (10)−0.0025 (6)−0.0243 (7)−0.0124 (7)
C60.0647 (10)0.0668 (11)0.0898 (12)0.0028 (8)−0.0416 (9)−0.0067 (9)
C70.0926 (15)0.0659 (12)0.160 (2)0.0136 (11)−0.0783 (16)−0.0153 (14)
C80.0408 (7)0.0543 (8)0.0487 (8)−0.0069 (6)−0.0157 (6)−0.0054 (6)
C90.0419 (7)0.0492 (8)0.0451 (7)−0.0076 (6)−0.0106 (6)0.0002 (6)
C100.0441 (7)0.0511 (8)0.0455 (7)−0.0101 (6)−0.0036 (6)−0.0038 (6)
C110.0632 (10)0.0676 (10)0.0542 (9)−0.0122 (8)−0.0078 (7)−0.0108 (8)
C120.0831 (13)0.0647 (11)0.0676 (11)−0.0099 (10)0.0027 (10)−0.0208 (9)
C130.0658 (11)0.0590 (10)0.0824 (12)0.0019 (8)0.0056 (10)−0.0102 (9)
C140.0501 (9)0.0601 (10)0.0757 (11)−0.0017 (7)−0.0066 (8)0.0002 (9)
C150.0416 (7)0.0509 (8)0.0541 (8)−0.0063 (6)−0.0060 (6)0.0025 (7)
C160.0419 (8)0.0611 (9)0.0510 (8)−0.0103 (7)−0.0113 (6)−0.0005 (7)
C170.0397 (7)0.0519 (8)0.0492 (8)−0.0123 (6)−0.0079 (6)−0.0036 (6)
C180.0486 (8)0.0663 (10)0.0673 (10)−0.0096 (7)−0.0115 (7)−0.0196 (8)
C190.0693 (11)0.0951 (13)0.0718 (11)−0.0202 (10)−0.0151 (9)−0.0320 (10)
C200.0696 (12)0.1190 (16)0.0667 (11)−0.0226 (11)−0.0270 (9)−0.0210 (11)
C210.0524 (9)0.0937 (13)0.0696 (10)−0.0061 (9)−0.0252 (8)−0.0058 (10)
C220.0415 (7)0.0595 (9)0.0554 (8)−0.0073 (6)−0.0142 (6)−0.0012 (7)
C230.0434 (8)0.0534 (8)0.0593 (9)−0.0042 (6)−0.0130 (7)−0.0098 (7)
C240.0447 (8)0.0457 (8)0.0595 (9)−0.0032 (6)−0.0040 (7)−0.0129 (7)
C250.0574 (9)0.0658 (10)0.0840 (12)−0.0167 (8)−0.0055 (8)−0.0170 (9)
C260.0678 (11)0.0761 (13)0.0967 (15)−0.0269 (9)0.0106 (11)−0.0130 (11)
C270.0867 (14)0.0625 (11)0.0737 (12)−0.0086 (10)0.0195 (11)−0.0025 (9)
C280.0953 (14)0.0782 (12)0.0606 (10)−0.0041 (11)−0.0087 (10)−0.0026 (9)
C290.0639 (10)0.0646 (10)0.0596 (10)−0.0111 (8)−0.0076 (8)−0.0043 (8)
O10.0721 (8)0.0992 (9)0.0744 (8)−0.0310 (7)−0.0316 (6)−0.0031 (7)

Geometric parameters (Å, º)

C1—C21.532 (3)C14—C151.390 (2)
C1—H1A0.9600C14—H140.9300
C1—H1B0.9600C15—C161.462 (2)
C1—H1C0.9600C16—C211.388 (2)
C2—C71.374 (3)C16—C171.4026 (19)
C2—C31.375 (3)C17—C181.386 (2)
C3—C41.382 (3)C18—C191.382 (2)
C3—H30.9300C18—H180.9300
C4—C51.382 (2)C19—C201.378 (3)
C4—H40.9300C19—H190.9300
C5—C61.390 (2)C20—C211.373 (3)
C5—C81.5171 (19)C20—H200.9300
C6—C71.388 (3)C21—H210.9300
C6—H60.9300C22—C231.5091 (19)
C7—H70.9300C22—H22A0.9700
C8—C221.5186 (18)C22—H22B0.9700
C8—C91.5510 (18)C23—O11.2167 (17)
C8—H80.9800C23—C241.490 (2)
C9—C171.5099 (19)C24—C291.377 (2)
C9—C101.5141 (19)C24—C251.388 (2)
C9—H90.9800C25—C261.375 (2)
C10—C111.383 (2)C25—H250.9300
C10—C151.395 (2)C26—C271.363 (3)
C11—C121.389 (2)C26—H260.9300
C11—H110.9300C27—C281.373 (3)
C12—C131.380 (3)C27—H270.9300
C12—H120.9300C28—C291.386 (2)
C13—C141.365 (3)C28—H280.9300
C13—H130.9300C29—H290.9300
C2—C1—H1A109.5C15—C14—H14120.6
C2—C1—H1B109.5C14—C15—C10120.40 (15)
H1A—C1—H1B109.5C14—C15—C16131.16 (15)
C2—C1—H1C109.5C10—C15—C16108.37 (13)
H1A—C1—H1C109.5C21—C16—C17120.27 (15)
H1B—C1—H1C109.5C21—C16—C15130.73 (15)
C7—C2—C3117.6 (2)C17—C16—C15108.82 (13)
C7—C2—C1120.8 (3)C18—C17—C16119.94 (14)
C3—C2—C1121.6 (3)C18—C17—C9129.88 (13)
C2—C3—C4121.5 (2)C16—C17—C9110.01 (12)
C2—C3—H3119.3C19—C18—C17119.05 (15)
C4—C3—H3119.3C19—C18—H18120.5
C3—C4—C5121.37 (19)C17—C18—H18120.5
C3—C4—H4119.3C20—C19—C18120.66 (17)
C5—C4—H4119.3C20—C19—H19119.7
C4—C5—C6117.19 (15)C18—C19—H19119.7
C4—C5—C8124.00 (14)C21—C20—C19121.19 (16)
C6—C5—C8118.78 (14)C21—C20—H20119.4
C7—C6—C5120.8 (2)C19—C20—H20119.4
C7—C6—H6119.6C20—C21—C16118.86 (16)
C5—C6—H6119.6C20—C21—H21120.6
C2—C7—C6121.5 (2)C16—C21—H21120.6
C2—C7—H7119.2C23—C22—C8113.76 (11)
C6—C7—H7119.2C23—C22—H22A108.8
C5—C8—C22114.16 (12)C8—C22—H22A108.8
C5—C8—C9111.08 (11)C23—C22—H22B108.8
C22—C8—C9110.72 (10)C8—C22—H22B108.8
C5—C8—H8106.8H22A—C22—H22B107.7
C22—C8—H8106.8O1—C23—C24119.90 (13)
C9—C8—H8106.8O1—C23—C22120.24 (13)
C17—C9—C10102.26 (11)C24—C23—C22119.81 (13)
C17—C9—C8116.84 (11)C29—C24—C25118.31 (14)
C10—C9—C8114.00 (11)C29—C24—C23123.07 (13)
C17—C9—H9107.8C25—C24—C23118.61 (15)
C10—C9—H9107.8C26—C25—C24120.53 (18)
C8—C9—H9107.8C26—C25—H25119.7
C11—C10—C15120.21 (14)C24—C25—H25119.7
C11—C10—C9129.23 (14)C27—C26—C25120.48 (18)
C15—C10—C9110.51 (13)C27—C26—H26119.8
C10—C11—C12118.74 (17)C25—C26—H26119.8
C10—C11—H11120.6C26—C27—C28120.15 (17)
C12—C11—H11120.6C26—C27—H27119.9
C13—C12—C11120.51 (17)C28—C27—H27119.9
C13—C12—H12119.7C27—C28—C29119.50 (19)
C11—C12—H12119.7C27—C28—H28120.3
C14—C13—C12121.29 (17)C29—C28—H28120.3
C14—C13—H13119.4C24—C29—C28121.02 (16)
C12—C13—H13119.4C24—C29—H29119.5
C13—C14—C15118.86 (17)C28—C29—H29119.5
C13—C14—H14120.6
C7—C2—C3—C4−0.7 (3)C10—C15—C16—C21173.55 (14)
C1—C2—C3—C4−179.65 (18)C14—C15—C16—C17−178.32 (14)
C2—C3—C4—C50.3 (3)C10—C15—C16—C17−1.52 (15)
C3—C4—C5—C60.6 (2)C21—C16—C17—C181.7 (2)
C3—C4—C5—C8−177.22 (14)C15—C16—C17—C18177.33 (12)
C4—C5—C6—C7−1.2 (2)C21—C16—C17—C9−174.09 (12)
C8—C5—C6—C7176.79 (14)C15—C16—C17—C91.59 (14)
C3—C2—C7—C60.1 (3)C10—C9—C17—C18−176.22 (13)
C1—C2—C7—C6179.10 (19)C8—C9—C17—C1858.58 (18)
C5—C6—C7—C20.8 (3)C10—C9—C17—C16−1.03 (13)
C4—C5—C8—C22−10.92 (19)C8—C9—C17—C16−126.24 (12)
C6—C5—C8—C22171.25 (12)C16—C17—C18—C19−1.1 (2)
C4—C5—C8—C9115.14 (15)C9—C17—C18—C19173.70 (13)
C6—C5—C8—C9−62.69 (16)C17—C18—C19—C20−0.4 (2)
C5—C8—C9—C17−70.05 (15)C18—C19—C20—C211.3 (3)
C22—C8—C9—C1757.89 (16)C19—C20—C21—C16−0.7 (3)
C5—C8—C9—C10170.88 (11)C17—C16—C21—C20−0.8 (2)
C22—C8—C9—C10−61.18 (15)C15—C16—C21—C20−175.36 (14)
C17—C9—C10—C11177.56 (13)C5—C8—C22—C23−73.97 (16)
C8—C9—C10—C11−55.39 (18)C9—C8—C22—C23159.78 (12)
C17—C9—C10—C150.08 (13)C8—C22—C23—O1−24.5 (2)
C8—C9—C10—C15127.14 (12)C8—C22—C23—C24158.07 (12)
C15—C10—C11—C12−0.3 (2)O1—C23—C24—C29−177.53 (14)
C9—C10—C11—C12−177.51 (13)C22—C23—C24—C29−0.1 (2)
C10—C11—C12—C130.1 (2)O1—C23—C24—C251.5 (2)
C11—C12—C13—C140.0 (3)C22—C23—C24—C25178.93 (13)
C12—C13—C14—C150.1 (2)C29—C24—C25—C260.0 (2)
C13—C14—C15—C10−0.2 (2)C23—C24—C25—C26−179.05 (14)
C13—C14—C15—C16176.26 (14)C24—C25—C26—C27−0.3 (3)
C11—C10—C15—C140.3 (2)C25—C26—C27—C280.1 (3)
C9—C10—C15—C14178.05 (12)C26—C27—C28—C290.4 (3)
C11—C10—C15—C16−176.89 (11)C25—C24—C29—C280.5 (2)
C9—C10—C15—C160.85 (15)C23—C24—C29—C28179.53 (15)
C14—C15—C16—C21−3.2 (3)C27—C28—C29—C24−0.8 (3)

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the C10–C15 ring.

D—H···AD—HH···AD···AD—H···A
C27—H27···Cgi0.932.763.617 (2)154

Symmetry code: (i) −x+1, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5614).

References

  • Bruker (2001). SMART and SAINTBruker AXS Inc., Madison, Wisconsin, USA.
  • Kreyenschmidt, M., Klaerner, G., Fuhrer, T., Ashenhurst, J., Karg, S., Chen, W. D., Lee, V. Y., Scott, J. C. & Miller, R. D. (1998). Macromolecules, 31, 1099–1103.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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