organic papers
o592
Zhou, Hu, Lv and Xia C21H13FO doi:10.1107/S1600536805002655 Acta Cryst.(2005). E61, o592–o593 Acta Crystallographica Section E
Structure Reports Online
ISSN 1600-5368
10-(4-Fluorobenzylidene)anthrone
Wei Zhou, Weixiao Hu,* Luping Lv and Chunnian Xia
College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, People’s Republic of China
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study T= 296 K
Mean(C–C) = 0.002 A˚ Rfactor = 0.033 wRfactor = 0.103
Data-to-parameter ratio = 12.8
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2005 International Union of Crystallography Printed in Great Britain – all rights reserved
The title compound, C21H13FO, was prepared from anthrone
and 4-fluorobenzaldehyde. The central six-membered ring has an asymmetric boat conformation, in which the carbonyl C and the opposite C atom deviate from the plane of the other four atoms by 0.173 (2) and 0.319 (2) A˚ , respectively.
Comment
It has been reported recently that derivatives of 10-substituted anthrone have a high potential for anticancer activity (Paullet al., 1992). In a continuation of our work on the structure– activity relationships (SAR) of derivatives of 10-substituted anthrone (Hu & Zhou, 2004), we obtained crystals of the title compound, (I), which were prepared by reacting anthrone with 4-fluorobenzaldhyde. The structure of the product was determined by X-ray diffraction.
The molecular structure of (I) is illustrated in Fig. 1. Selected bond lengths and angles are listed in Table 1. Atoms C11–C14 are coplanar within 0.0055 (7) A˚ , while atoms C5 and C10 deviate from this plane by 0.173 (2) and 0.319 (2) A˚ , respectively.
Experimental
To a mixture of anthrone (4.0 g, 20 mmol) and 4-fluorobenzaldhyde (3.0 g, 24 mmol) were added pyridine (30 ml) and piperidine (0.5 g, 6 mmol). The reaction mixture was refluxed for 6 h. The completion of the reaction of the anthrone was confirmed by thin-layer chro-matography. The mixture was cooled to room temperature, poured into methanol (75 ml) and put in a refrigerator overnight. The precipitate was collected and recrystallized twice from acetic acid to afford yellow crystals (1.4 g, yield 23.3%, m.p. 378–381 K).
Crystal data
C21H13FO Mr= 300.31
Monoclinic,P21=c a= 10.044 (6) A˚
b= 11.398 (3) A˚
c= 13.820 (3) A˚
= 109.79 (4)
V= 1488.7 (10) A˚3
Z= 4
Dx= 1.340 Mg m
3
MoKradiation Cell parameters from 25
reflections
= 11.1–12.7
= 0.09 mm1 T= 296 (2) K Prism, colorless 0.500.400.40 mm
Data collection
Enraf–Nonius CAD-4 diffractometer
!/2scans
Absorption correction: none 3137 measured reflections 2673 independent reflections 2026 reflections withI> 2(I)
Rint= 0.012
max= 25.2
h= 0!12
k=1!13
l=16!15 3 standard reflections
frequency: 60 min intensity decay: none
Refinement
Refinement onF2 R[F2> 2(F2)] = 0.033 wR(F2) = 0.103
S= 1.04 2673 reflections 209 parameters
H-atom parameters constrained
w= 1/[2
(Fo 2
) + (0.0525P)2 + 0.247P]
whereP= (Fo2+ 2Fc2)/3
(/)max< 0.001
max= 0.18 e A˚
3
min=0.14 e A˚
3
Extinction correction:SHELXL97
Extinction coefficient: 0.0058 (11)
Table 1
Selected geometric parameters (A˚ ,).
F1—C19 1.3598 (19) O1—C10 1.2209 (17)
C5—C15 1.338 (2) C15—C16 1.470 (2) C15—C5—C13 125.88 (13)
C15—C5—C14 118.82 (12) O1—C10—C11 121.44 (14)
O1—C10—C12 121.76 (14) C17—C16—C15 118.41 (13) C21—C16—C15 123.65 (13) C13—C5—C15—C16 4.4 (2)
C14—C5—C15—C16 171.30 (14)
C5—C15—C16—C17 146.85 (16) C5—C15—C16—C21 37.3 (2)
The H atoms were placed in calculated positions (C—H = 0.93 A˚ ) and refined using a riding model, withUiso(H) = 1.2Ueq(parent atom).
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction:XCAD4 (Harms &
Wocadlo, 1995); 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:
SHELXL97.
We are grateful to the National Natural and Scientific Foundation (grant No. 20272053) and Zhejiang Natural and Scientific Foundation (grant No. 011101937) for financial support.
References
Enraf–Nonius (1994).CAD-4 EXPRESS. Enraf–Nonius, Delft, The Nether-lands.
Farrugia, L. J. (1997).J. Appl. Cryst.30, 565.
Harms, K. & Wocadlo, S. (1995).XCAD4. University of Marburg, Germany. Hu, W. X. & Zhou, W. (2004).Bioorg. Med. Chem. Lett.14, 621–622. Paull, K. D., Lin, C. M., Malspeis, L. & Hamel, E. (1992).Cancer Res.52, 3892–
3900.
[image:2.610.315.563.70.252.2]Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Go¨ttingen, Germany.
Figure 1
supporting information
sup-1 Acta Cryst. (2005). E61, o592–o593
supporting information
Acta Cryst. (2005). E61, o592–o593 [https://doi.org/10.1107/S1600536805002655]
10-(4-Fluorobenzylidene)anthrone
Wei Zhou, Weixiao Hu, Luping Lv and Chunnian Xia
10-(4-Fluorobenzylidene)anthrone
Crystal data C21H13FO
Mr = 300.31
Monoclinic, P21/c
Hall symbol: -P 2ybc a = 10.044 (6) Å b = 11.398 (3) Å c = 13.820 (3) Å β = 109.79 (4)° V = 1488.7 (10) Å3
Z = 4
F(000) = 624 Dx = 1.340 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 25 reflections θ = 11.1–12.7°
µ = 0.09 mm−1
T = 296 K Prism, colorless 0.50 × 0.40 × 0.40 mm
Data collection Enraf–Nonius CAD-4
diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
ω/2θ scans
3137 measured reflections 2673 independent reflections 2026 reflections with I > 2σ(I)
Rint = 0.012
θmax = 25.2°, θmin = 2.2°
h = 0→12 k = −1→13 l = −16→15
3 standard reflections every 60 min intensity decay: none
Refinement Refinement on F2
Least-squares matrix: full R[F2 > 2σ(F2)] = 0.033
wR(F2) = 0.103
S = 1.04 2673 reflections 209 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained w = 1/[σ2(F
o2) + (0.0525P)2 + 0.247P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.18 e Å−3
Δρmin = −0.14 e Å−3
Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
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)
x y z Uiso*/Ueq
F1 0.46323 (12) 1.13505 (10) 0.22408 (10) 0.0977 (4) O1 0.04833 (13) 0.33472 (9) 0.13091 (9) 0.0663 (3) C1 −0.21168 (17) 0.43485 (14) 0.01400 (11) 0.0580 (4)
H1 −0.2023 0.3541 0.0092 0.070*
C2 −0.33601 (18) 0.48835 (17) −0.04179 (13) 0.0685 (5)
H2 −0.4111 0.4442 −0.0841 0.082*
C3 −0.34915 (17) 0.60847 (17) −0.03479 (13) 0.0670 (5)
H3 −0.4344 0.6447 −0.0711 0.080*
C4 −0.23743 (15) 0.67491 (15) 0.02528 (11) 0.0569 (4)
H4 −0.2474 0.7559 0.0278 0.068*
C5 0.01670 (14) 0.69201 (12) 0.14295 (10) 0.0440 (3) C6 0.20273 (15) 0.68760 (14) 0.31943 (10) 0.0522 (4)
H6 0.1967 0.7688 0.3236 0.063*
C7 0.29415 (16) 0.62594 (16) 0.40089 (11) 0.0614 (4)
H7 0.3481 0.6658 0.4598 0.074*
C8 0.30632 (17) 0.50583 (16) 0.39572 (12) 0.0637 (4)
H8 0.3696 0.4651 0.4504 0.076*
C9 0.22484 (16) 0.44651 (14) 0.30976 (12) 0.0555 (4)
H9 0.2334 0.3655 0.3061 0.067*
C10 0.03015 (15) 0.43892 (13) 0.14268 (10) 0.0481 (3) C11 −0.09878 (15) 0.50051 (13) 0.07809 (10) 0.0469 (3) C12 0.12921 (14) 0.50705 (13) 0.22794 (10) 0.0464 (3) C13 0.11917 (14) 0.62930 (12) 0.23078 (10) 0.0440 (3) C14 −0.10890 (14) 0.62261 (13) 0.08273 (10) 0.0458 (3) C15 0.03268 (14) 0.80040 (13) 0.11125 (10) 0.0484 (3)
H15 −0.0457 0.8274 0.0579 0.058*
C16 0.14984 (15) 0.88502 (12) 0.14427 (10) 0.0465 (3) C17 0.11758 (15) 1.00391 (13) 0.13936 (11) 0.0518 (4)
H17 0.0232 1.0269 0.1168 0.062*
C18 0.22135 (18) 1.08850 (14) 0.16698 (12) 0.0610 (4)
H18 0.1984 1.1677 0.1651 0.073*
C19 0.35952 (18) 1.05237 (15) 0.19737 (13) 0.0632 (4) C20 0.39741 (17) 0.93670 (15) 0.20095 (13) 0.0620 (4)
H20 0.4921 0.9150 0.2209 0.074*
supporting information
sup-3 Acta Cryst. (2005). E61, o592–o593
H21 0.3165 0.7743 0.1765 0.063*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
F1 0.0777 (7) 0.0807 (8) 0.1135 (9) −0.0333 (6) 0.0046 (6) 0.0053 (6) O1 0.0806 (8) 0.0472 (7) 0.0663 (7) 0.0053 (5) 0.0185 (6) −0.0010 (5) C1 0.0670 (10) 0.0566 (9) 0.0463 (8) −0.0126 (7) 0.0139 (7) −0.0021 (7) C2 0.0587 (10) 0.0786 (12) 0.0557 (9) −0.0172 (9) 0.0031 (8) −0.0046 (8) C3 0.0474 (9) 0.0798 (12) 0.0617 (10) 0.0008 (8) 0.0025 (7) 0.0004 (9) C4 0.0495 (8) 0.0606 (9) 0.0528 (8) 0.0037 (7) 0.0071 (7) −0.0026 (7) C5 0.0423 (7) 0.0470 (8) 0.0399 (7) 0.0037 (6) 0.0105 (6) −0.0024 (6) C6 0.0518 (8) 0.0559 (8) 0.0447 (8) 0.0007 (7) 0.0109 (6) −0.0008 (6) C7 0.0534 (9) 0.0759 (11) 0.0451 (8) −0.0039 (8) 0.0040 (7) 0.0004 (7) C8 0.0509 (8) 0.0739 (11) 0.0551 (9) 0.0044 (8) 0.0034 (7) 0.0170 (8) C9 0.0501 (8) 0.0546 (9) 0.0588 (9) 0.0063 (7) 0.0145 (7) 0.0112 (7) C10 0.0552 (8) 0.0460 (8) 0.0457 (8) 0.0006 (6) 0.0204 (7) 0.0023 (6) C11 0.0510 (8) 0.0504 (8) 0.0393 (7) −0.0046 (6) 0.0151 (6) −0.0001 (6) C12 0.0431 (7) 0.0522 (8) 0.0446 (7) 0.0045 (6) 0.0159 (6) 0.0057 (6) C13 0.0408 (7) 0.0497 (8) 0.0414 (7) 0.0017 (6) 0.0137 (6) 0.0012 (6) C14 0.0446 (7) 0.0523 (8) 0.0385 (7) −0.0008 (6) 0.0114 (6) −0.0008 (6) C15 0.0442 (7) 0.0486 (8) 0.0458 (7) 0.0051 (6) 0.0067 (6) 0.0011 (6) C16 0.0477 (7) 0.0465 (8) 0.0412 (7) 0.0025 (6) 0.0098 (6) 0.0029 (6) C17 0.0495 (8) 0.0508 (8) 0.0516 (8) 0.0067 (7) 0.0123 (6) 0.0064 (6) C18 0.0706 (11) 0.0441 (8) 0.0630 (10) −0.0007 (7) 0.0157 (8) 0.0045 (7) C19 0.0600 (10) 0.0592 (10) 0.0601 (9) −0.0148 (8) 0.0068 (7) 0.0045 (8) C20 0.0448 (8) 0.0708 (11) 0.0631 (10) 0.0003 (7) 0.0088 (7) 0.0092 (8) C21 0.0501 (8) 0.0490 (8) 0.0552 (8) 0.0067 (7) 0.0124 (7) 0.0046 (6)
Geometric parameters (Å, º)
F1—C19 1.3598 (19) C8—H8 0.9300
O1—C10 1.2209 (17) C9—C12 1.394 (2)
C1—C2 1.369 (2) C9—H9 0.9300
C1—C11 1.397 (2) C10—C11 1.478 (2)
C1—H1 0.9300 C10—C12 1.479 (2)
C2—C3 1.382 (3) C11—C14 1.398 (2)
C2—H2 0.9300 C12—C13 1.399 (2)
C3—C4 1.375 (2) C15—C16 1.470 (2)
C3—H3 0.9300 C15—H15 0.9300
C4—C14 1.399 (2) C16—C17 1.390 (2)
C4—H4 0.9300 C16—C21 1.396 (2)
C5—C15 1.338 (2) C17—C18 1.376 (2)
C5—C13 1.4824 (19) C17—H17 0.9300
C5—C14 1.483 (2) C18—C19 1.370 (3)
C6—C7 1.380 (2) C18—H18 0.9300
C6—C13 1.397 (2) C19—C20 1.368 (2)
C7—C8 1.378 (2) C20—H20 0.9300
C7—H7 0.9300 C21—H21 0.9300
C8—C9 1.371 (2)
C2—C1—C11 120.56 (16) C14—C11—C10 120.50 (13)
C2—C1—H1 119.7 C9—C12—C13 120.47 (14)
C11—C1—H1 119.7 C9—C12—C10 118.65 (13)
C1—C2—C3 119.50 (15) C13—C12—C10 120.66 (13)
C1—C2—H2 120.2 C6—C13—C12 118.10 (13)
C3—C2—H2 120.2 C6—C13—C5 122.23 (13)
C4—C3—C2 120.67 (16) C12—C13—C5 119.61 (12)
C4—C3—H3 119.7 C11—C14—C4 117.73 (13)
C2—C3—H3 119.7 C11—C14—C5 119.69 (13)
C3—C4—C14 121.03 (16) C4—C14—C5 122.51 (14)
C3—C4—H4 119.5 C5—C15—C16 132.55 (13)
C14—C4—H4 119.5 C5—C15—H15 113.7
C15—C5—C13 125.88 (13) C16—C15—H15 113.7
C15—C5—C14 118.82 (12) C17—C16—C21 117.81 (14) C13—C5—C14 115.17 (12) C17—C16—C15 118.41 (13) C7—C6—C13 120.63 (15) C21—C16—C15 123.65 (13)
C7—C6—H6 119.7 C18—C17—C16 121.85 (14)
C13—C6—H6 119.7 C18—C17—H17 119.1
C8—C7—C6 120.64 (15) C16—C17—H17 119.1
C8—C7—H7 119.7 C19—C18—C17 117.91 (15)
C6—C7—H7 119.7 C19—C18—H18 121.0
C9—C8—C7 119.82 (15) C17—C18—H18 121.0
C9—C8—H8 120.1 F1—C19—C20 118.67 (16)
C7—C8—H8 120.1 F1—C19—C18 118.57 (16)
C8—C9—C12 120.27 (15) C20—C19—C18 122.76 (15)
C8—C9—H9 119.9 C19—C20—C21 118.54 (15)
C12—C9—H9 119.9 C19—C20—H20 120.7
O1—C10—C11 121.44 (14) C21—C20—H20 120.7
O1—C10—C12 121.76 (14) C20—C21—C16 121.09 (15) C11—C10—C12 116.57 (13) C20—C21—H21 119.5
C1—C11—C14 120.42 (14) C16—C21—H21 119.5
C1—C11—C10 119.07 (14)
supporting information
sup-5 Acta Cryst. (2005). E61, o592–o593
