Literature DB >> 22719717

(E)-3-(4-Cyclo-hexyl-3-fluoro-benzyl-idene)chroman-4-one.

Kaalin Gopaul, Mahidansha M Shaikh, Neil A Koorbanally, Deresh Ramjugernath, Bernard Omondi.   

Abstract

The title compound, C(22)H(21)FO(2), exhibits substitutional disorder of the F atom and a H atom in the asymmetric unit with different occupancies, the refined F:H ratio being 0.80 (2):0.20 (2). The dihedral angle between the fluorinated benzene ring and the benzene ring of the chromanone system is 37.30°. There are two relatively high residual electron-density peaks associated with the disorder.

Entities:  

Year:  2012        PMID： 22719717      PMCID： PMC3379519          DOI： 10.1107/S1600536812024336

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the preparation, see: Shaikh et al. (2011 ▶). For related structures, see: Gopaul et al. (2012 ▶); Marx et al. (2008 ▶); Suresh et al. (2007 ▶). For the biological activity of this class of compound, see: du Toit et al. (2010 ▶). This compound may undergo chemical conversion into the (E)- and (Z)-isomers, see: Kirkiacharian et al. (1984 ▶).

Experimental

Crystal data

C22H21FO2 M = 336.39 Triclinic, a = 6.8351 (1) Å b = 8.1483 (2) Å c = 15.7931 (3) Å α = 76.661 (1)° β = 81.769 (1)° γ = 75.287 (1)° V = 824.45 (3) Å3 Z = 2 Mo Kα radiation μ = 0.09 mm−1 T = 446 K 0.34 × 0.33 × 0.19 mm

Data collection

Bruker SMART APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.969, T max = 0.983 18883 measured reflections 4104 independent reflections 3637 reflections with I > 2σ(I) R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.058 wR(F 2) = 0.173 S = 1.05 4104 reflections 233 parameters 21 restraints H-atom parameters constrained Δρmax = 0.96 e Å−3 Δρmin = −1.05 e Å−3 Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812024336/fj2556sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024336/fj2556Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C22H21FO2Z = 2
Mr = 336.39F(000) = 356
Triclinic, P1Dx = 1.355 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.8351 (1) ÅCell parameters from 18935 reflections
b = 8.1483 (2) Åθ = 2.6–28.5°
c = 15.7931 (3) ŵ = 0.09 mm−1
α = 76.661 (1)°T = 446 K
β = 81.769 (1)°Block, yellow
γ = 75.287 (1)°0.34 × 0.33 × 0.19 mm
V = 824.45 (3) Å3
Bruker SMART APEXII CCD diffractometer3637 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
φ and ω scansθmax = 28.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)h = −9→9
Tmin = 0.969, Tmax = 0.983k = −8→10
18883 measured reflectionsl = −21→21
4104 independent reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0944P)2 + 0.7446P] where P = (Fo2 + 2Fc2)/3
4104 reflections(Δ/σ)max < 0.001
233 parametersΔρmax = 0.96 e Å−3
21 restraintsΔρmin = −1.05 e Å−3
Experimental. Carbon-bound H-atoms were placed in calculated positions [C—H = 0.97 Å for Methylene H atoms, 0.98 Å for methine and 0.93 Å for aromatic H atoms; Uiso(H) = 1.2Ueq(C)] and were included in the refinement in the riding model approximation. Disorder: Disorder was found for the F– and H-atoms, which is not an uncommon situation. The disorder was modelled for F– and H– atoms (80:30) using PART instructions and the total occupancy at each atom site was kept as 1 during the refinement by means of a SUMFIX constraint. The F-atoms involved in disorder were modelled with anisotropic thermal parameters.
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.
xyzUiso*/UeqOcc. (<1)
C10.2972 (3)0.3337 (3)0.18026 (11)0.0240 (4)
H1A0.43750.26910.17750.029*
H1B0.2970.45580.17020.029*
C20.1930 (3)0.3034 (3)0.10912 (11)0.0256 (4)
H2A0.2150.17980.11260.031*
H2B0.25310.35320.05270.031*
C3−0.0336 (3)0.3826 (3)0.11618 (12)0.0269 (4)
H3A−0.05660.50790.10010.032*
H3B−0.09780.34430.07570.032*
C4−0.1284 (3)0.3313 (3)0.20779 (12)0.0276 (4)
H4A−0.1290.20930.21930.033*
H4B−0.26830.39640.21220.033*
C5−0.0171 (2)0.3636 (3)0.27620 (11)0.0252 (4)
H5A−0.03370.48740.27040.03*
H5B−0.07590.31860.33380.03*
C60.1987 (2)0.28131 (19)0.26771 (9)0.0131 (3)
H60.19780.16040.26960.016*
C70.3101 (2)0.2672 (2)0.33810 (10)0.0158 (3)
C80.2403 (2)0.3561 (2)0.40676 (10)0.0181 (3)
H80.11230.43060.40630.022*0.803 (4)
F1B0.0633 (2)0.4701 (2)0.41034 (10)0.0309 (17)0.197 (4)
C100.3560 (2)0.3365 (2)0.47542 (10)0.0178 (3)
H100.30380.39820.51950.021*
C110.5499 (2)0.22563 (19)0.47953 (10)0.0160 (3)
C120.6215 (2)0.13448 (19)0.41124 (10)0.0164 (3)
H120.74960.05990.41140.02*
C130.5036 (2)0.15504 (19)0.34448 (10)0.0161 (3)
H130.55450.09130.30110.019*0.197 (4)
F1A0.57542 (18)0.05863 (15)0.28206 (8)0.0190 (4)0.803 (4)
C140.6861 (2)0.1993 (2)0.54697 (10)0.0170 (3)
H140.82150.15220.53110.02*
C150.6495 (2)0.23152 (19)0.62847 (10)0.0159 (3)
C160.4451 (2)0.3066 (2)0.67092 (10)0.0183 (3)
H16A0.42370.43180.65820.022*
H16B0.34130.27790.64480.022*
C170.5798 (2)0.2205 (2)0.81068 (10)0.0180 (3)
C180.5371 (3)0.2086 (2)0.90100 (11)0.0231 (3)
H180.4040.21920.92610.028*
C190.6940 (3)0.1809 (2)0.95265 (11)0.0239 (4)
H190.66570.17281.01270.029*
C200.8948 (3)0.1650 (2)0.91576 (11)0.0223 (3)
H200.99910.14950.95080.027*
C210.9374 (2)0.1725 (2)0.82692 (11)0.0196 (3)
H211.07120.1590.80250.023*
C220.7803 (2)0.20013 (19)0.77313 (10)0.0165 (3)
C230.8274 (2)0.1979 (2)0.67917 (10)0.0180 (3)
O10.41878 (17)0.24763 (18)0.76439 (8)0.0230 (3)
O21.00278 (19)0.1688 (2)0.64622 (9)0.0303 (3)
U11U22U33U12U13U23
C10.0204 (8)0.0353 (9)0.0172 (7)−0.0094 (7)0.0026 (6)−0.0064 (6)
C20.0245 (8)0.0333 (9)0.0185 (8)−0.0042 (7)−0.0007 (6)−0.0081 (7)
C30.0239 (8)0.0373 (10)0.0222 (8)−0.0083 (7)−0.0058 (6)−0.0078 (7)
C40.0189 (8)0.0393 (10)0.0255 (9)−0.0077 (7)−0.0028 (6)−0.0070 (7)
C50.0147 (7)0.0397 (10)0.0221 (8)−0.0066 (6)0.0001 (6)−0.0085 (7)
C60.0111 (6)0.0177 (7)0.0106 (6)−0.0035 (5)−0.0004 (5)−0.0031 (5)
C70.0165 (7)0.0173 (7)0.0144 (6)−0.0067 (5)−0.0008 (5)−0.0020 (5)
C80.0161 (7)0.0170 (7)0.0197 (7)−0.0019 (5)0.0003 (5)−0.0042 (6)
F1B0.023 (3)0.034 (3)0.032 (3)0.009 (2)−0.007 (2)−0.014 (2)
C100.0189 (7)0.0172 (7)0.0166 (7)−0.0026 (6)0.0006 (5)−0.0053 (5)
C110.0168 (7)0.0154 (7)0.0160 (7)−0.0054 (5)0.0006 (5)−0.0029 (5)
C120.0154 (7)0.0151 (7)0.0181 (7)−0.0034 (5)0.0007 (5)−0.0034 (5)
C130.0188 (7)0.0143 (7)0.0158 (7)−0.0049 (5)0.0017 (5)−0.0047 (5)
F1A0.0210 (6)0.0186 (6)0.0182 (6)−0.0015 (4)−0.0006 (4)−0.0093 (4)
C140.0151 (7)0.0161 (7)0.0194 (7)−0.0024 (5)−0.0004 (5)−0.0051 (5)
C150.0133 (6)0.0159 (7)0.0184 (7)−0.0031 (5)−0.0001 (5)−0.0045 (5)
C160.0137 (7)0.0242 (8)0.0158 (7)−0.0025 (6)0.0006 (5)−0.0047 (6)
C170.0168 (7)0.0190 (7)0.0189 (7)−0.0044 (5)−0.0020 (6)−0.0046 (6)
C180.0197 (7)0.0292 (9)0.0197 (8)−0.0053 (6)0.0010 (6)−0.0057 (6)
C190.0283 (9)0.0262 (8)0.0180 (7)−0.0070 (7)−0.0029 (6)−0.0046 (6)
C200.0240 (8)0.0218 (8)0.0232 (8)−0.0064 (6)−0.0082 (6)−0.0037 (6)
C210.0172 (7)0.0192 (7)0.0234 (8)−0.0046 (6)−0.0035 (6)−0.0050 (6)
C220.0155 (7)0.0153 (7)0.0190 (7)−0.0029 (5)−0.0020 (5)−0.0043 (5)
C230.0142 (7)0.0199 (7)0.0205 (7)−0.0025 (5)−0.0007 (5)−0.0076 (6)
O10.0133 (5)0.0381 (7)0.0171 (6)−0.0064 (5)0.0002 (4)−0.0048 (5)
O20.0140 (6)0.0507 (9)0.0273 (7)−0.0028 (5)0.0010 (5)−0.0172 (6)
C1—C61.467 (2)C11—C141.457 (2)
C1—C21.509 (2)C12—C131.372 (2)
C1—H1A0.97C12—H120.93
C1—H1B0.97C13—F1A1.3611 (18)
C2—C31.518 (2)C13—H130.93
C2—H2A0.97C14—C151.349 (2)
C2—H2B0.97C14—H140.93
C3—C41.509 (3)C15—C231.484 (2)
C3—H3A0.97C15—C161.504 (2)
C3—H3B0.97C16—O11.4433 (19)
C4—C51.511 (2)C16—H16A0.97
C4—H4A0.97C16—H16B0.97
C4—H4B0.97C17—O11.3517 (19)
C5—C61.458 (2)C17—C221.398 (2)
C5—H5A0.97C17—C181.400 (2)
C5—H5B0.97C18—C191.382 (2)
C6—C71.403 (2)C18—H180.93
C6—H60.98C19—C201.399 (3)
C7—C81.402 (2)C19—H190.93
C7—C131.406 (2)C20—C211.382 (2)
C8—F1B1.3282C20—H200.93
C8—C101.389 (2)C21—C221.405 (2)
C8—H80.93C21—H210.93
C10—C111.402 (2)C22—C231.476 (2)
C10—H100.93C23—O21.224 (2)
C11—C121.410 (2)
C6—C1—C2112.53 (14)C11—C10—H10119.4
C6—C1—H1A109.1C10—C11—C12117.11 (14)
C2—C1—H1A109.1C10—C11—C14125.82 (14)
C6—C1—H1B109.1C12—C11—C14117.04 (14)
C2—C1—H1B109.1C13—C12—C11120.46 (14)
H1A—C1—H1B107.8C13—C12—H12119.8
C1—C2—C3112.13 (14)C11—C12—H12119.8
C1—C2—H2A109.2F1A—C13—C12118.33 (14)
C3—C2—H2A109.2F1A—C13—C7118.06 (14)
C1—C2—H2B109.2C12—C13—C7123.59 (14)
C3—C2—H2B109.2C12—C13—H13118.2
H2A—C2—H2B107.9C7—C13—H13118.2
C4—C3—C2111.15 (15)C15—C14—C11131.10 (14)
C4—C3—H3A109.4C15—C14—H14114.5
C2—C3—H3A109.4C11—C14—H14114.5
C4—C3—H3B109.4C14—C15—C23117.23 (14)
C2—C3—H3B109.4C14—C15—C16125.62 (14)
H3A—C3—H3B108C23—C15—C16117.08 (13)
C3—C4—C5112.63 (15)O1—C16—C15114.82 (13)
C3—C4—H4A109.1O1—C16—H16A108.6
C5—C4—H4A109.1C15—C16—H16A108.6
C3—C4—H4B109.1O1—C16—H16B108.6
C5—C4—H4B109.1C15—C16—H16B108.6
H4A—C4—H4B107.8H16A—C16—H16B107.5
C6—C5—C4111.53 (15)O1—C17—C22123.41 (14)
C6—C5—H5A109.3O1—C17—C18116.25 (14)
C4—C5—H5A109.3C22—C17—C18120.32 (15)
C6—C5—H5B109.3C19—C18—C17119.57 (15)
C4—C5—H5B109.3C19—C18—H18120.2
H5A—C5—H5B108C17—C18—H18120.2
C7—C6—C5117.07 (13)C18—C19—C20120.78 (16)
C7—C6—C1116.12 (13)C18—C19—H19119.6
C5—C6—C1112.93 (13)C20—C19—H19119.6
C7—C6—H6102.6C21—C20—C19119.60 (15)
C5—C6—H6102.6C21—C20—H20120.2
C1—C6—H6102.6C19—C20—H20120.2
C8—C7—C6124.42 (14)C20—C21—C22120.61 (15)
C8—C7—C13115.31 (14)C20—C21—H21119.7
C6—C7—C13120.25 (14)C22—C21—H21119.7
F1B—C8—C10114.28 (9)C17—C22—C21119.08 (14)
F1B—C8—C7123.45 (9)C17—C22—C23120.42 (14)
C10—C8—C7122.22 (14)C21—C22—C23120.41 (14)
C10—C8—H8118.9O2—C23—C22121.42 (15)
C7—C8—H8118.9O2—C23—C15122.84 (15)
C8—C10—C11121.29 (14)C22—C23—C15115.73 (13)
C8—C10—H10119.4C17—O1—C16118.16 (12)
C6—C1—C2—C351.8 (2)C10—C11—C14—C1519.5 (3)
C1—C2—C3—C4−49.7 (2)C12—C11—C14—C15−162.10 (17)
C2—C3—C4—C550.9 (2)C11—C14—C15—C23−176.66 (15)
C3—C4—C5—C6−53.7 (2)C11—C14—C15—C160.3 (3)
C4—C5—C6—C7−165.85 (15)C14—C15—C16—O1148.36 (16)
C4—C5—C6—C155.3 (2)C23—C15—C16—O1−34.7 (2)
C2—C1—C6—C7165.83 (15)O1—C17—C18—C19179.99 (15)
C2—C1—C6—C5−54.9 (2)C22—C17—C18—C191.7 (3)
C5—C6—C7—C8−13.6 (2)C17—C18—C19—C200.1 (3)
C1—C6—C7—C8123.94 (17)C18—C19—C20—C21−1.7 (3)
C5—C6—C7—C13164.76 (15)C19—C20—C21—C221.6 (2)
C1—C6—C7—C13−57.7 (2)O1—C17—C22—C21−179.98 (14)
C6—C7—C8—F1B−3.22 (19)C18—C17—C22—C21−1.8 (2)
C13—C7—C8—F1B178.34 (9)O1—C17—C22—C23−3.4 (2)
C6—C7—C8—C10179.45 (15)C18—C17—C22—C23174.79 (15)
C13—C7—C8—C101.0 (2)C20—C21—C22—C170.2 (2)
F1B—C8—C10—C11−177.69 (11)C20—C21—C22—C23−176.43 (15)
C7—C8—C10—C11−0.1 (2)C17—C22—C23—O2−175.13 (16)
C8—C10—C11—C12−0.3 (2)C21—C22—C23—O21.4 (2)
C8—C10—C11—C14178.12 (14)C17—C22—C23—C154.4 (2)
C10—C11—C12—C13−0.2 (2)C21—C22—C23—C15−179.02 (14)
C14—C11—C12—C13−178.77 (14)C14—C15—C23—O211.4 (2)
C11—C12—C13—F1A−177.15 (13)C16—C15—C23—O2−165.74 (16)
C11—C12—C13—C71.2 (2)C14—C15—C23—C22−168.11 (14)
C8—C7—C13—F1A176.79 (13)C16—C15—C23—C2214.7 (2)
C6—C7—C13—F1A−1.7 (2)C22—C17—O1—C16−18.0 (2)
C8—C7—C13—C12−1.6 (2)C18—C17—O1—C16163.70 (15)
C6—C7—C13—C12179.93 (14)C15—C16—O1—C1736.5 (2)
  4 in total

Review 1.  The chemical structures, plant origins, ethnobotany and biological activities of homoisoflavanones.

Authors:  Karen du Toit; Siegfried E Drewes; Johannes Bodenstein
Journal:  Nat Prod Res       Date:  2010-03       Impact factor: 2.861

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  8-Eth-oxy-3-(4-isopropyl-benzyl-idene)-6-methyl-chroman-4-one.

Authors:  A Marx; V Manivannan; R Suresh; Charles C Kanagam; B Sridhar
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2007-12-21

4.  3-(3-Meth-oxy-benzyl-idene)chroman-4-one.

Authors:  Kaalin Gopaul; Mahidansha Shaikh; Deresh Ramjugernath; Neil A Koorbanally; Bernard Omondi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-03-10
  4 in total
  1 in total

1.  Crystal structures of (E)-3-(4-hy-droxy-benzyl-idene)chroman-4-one and (E)-3-(3-hy-droxy-benzyl-idene)-2-phenyl-chroman-4-one.

Authors:  Kamil Suchojad; Anna Dołęga; Angelika Adamus-Grabicka; Elżbieta Budzisz; Magdalena Małecka
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2019-11-22
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.