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In the title compound, C24H22O2, both six-membered heterocyclic rings adopt a distorted envelope conformation. The mean planes passing through these rings are nearly perpendicular to each other [dihedral angle 88.39 (7)°].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801001970/ci6004sup1.cif
Contains datablocks 1, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801001970/ci6004Isup2.hkl
Contains datablock I

CCDC reference: 159845

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.050
  • wR factor = 0.134
  • Data-to-parameter ratio = 13.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry




Comment top

The title compound, (I), was synthesized with a view to screen it for antimalarial activity. Before studying the activity, the X-ray structure determination was taken up. In (I), both the heterocyclic rings B and C adopt a distorted envelope conformation; the puckering parameters are: Q = 0.526 (2) Å, θ = 124.7° and ϕ = 309.47 (1)° for ring B and Q = 0.505 (2) Å, θ =130.5 (2)° and ϕ = 65.54 (2)° for ring C, respectively (Cremer & Pople, 1975). Atom C17 deviates from the best plane passing through atoms C1/C2/C7/O8/C9 by 0.715 (2) Å and similarly the deviation of C17 from the best plane through C9/O10/C11/C16/C1 is -0.688 (2) Å. The mean planes through the two heterocyclic rings B and C are nearly perpendicular to each other [dihedral angle 88.39 (7)°]. The phenyl ring at C9 is equatorially attached to the rings B and C and with them it make dihedral angles of 70.52 (8) and 19.04 (8)°, respectively. The methyl group at C1 is pseudoequatorially disposed [C18—C1—C16—C11 - 148.1 (1)° and C18—C1—C2—C7 152.9 (1)°]. In the crystal, C—H···π interactions involving rings A and D are observed [C18—H181···CgA(x, -1 + y, z), with H···Cg 2.70, C18···Cg 3.612 (2) Å and X—H···Cg 158°; C18—H182···CgD(x, -1 + y, z), with H···Cg 2.74, X···Cg 3.666 (2) Å and X—H···Cg 161°].

Experimental top

A mixture of 4-methyl phenol (0.05 mol) and benzoylacetone (0.05 mol) were mixed throughly. 80% of sulfuric acid (15 ml) was added gradually with constant stirring. The reacting mixture was cooled in an ice-bath during the addition. It was kept overnight at room temperature and then poured over crushed ice with constant stirring. The resulting solid was filtered, washed with water and then with a dilute sodium hydroxide solution followed by water to remove unreacted substances. It was dried and crystallized from ethanol as colourless single crystals (yield 60%; m.p. 333 K).

Refinement top

All H atoms were fixed using geometrical considerations and their overall displacement parameters were refined.

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: MolEN (Fair, 1990); data reduction: MolEN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolanai, 1997); software used to prepare material for publication: SHELXL97 and PARST95 (Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids.
1,5,13-trimethyl-8,10-dioxa-9-phenyl tetracyclo[7.7.1.02701116] heptadeca-2,4,6,11,13,15-hexaene top
Crystal data top
C24H22O2F(000) = 728
Mr = 342.42Dx = 1.281 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 17.7903 (15) ÅCell parameters from 25 reflections
b = 5.5559 (5) Åθ = 2–25°
c = 18.0320 (17) ŵ = 0.08 mm1
β = 94.815 (8)°T = 293 K
V = 1776.0 (3) Å3Needle, white
Z = 40.20 × 0.15 × 0.12 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
2918 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
Graphite monochromatorθmax = 25.3°, θmin = 1.2°
ω–2θ scansh = 021
Absorption correction: ψ scan
(North et al., 1968
k = 06
Tmin = 0.982, Tmax = 0.994l = 2121
3351 measured reflections3 standard reflections every 100 reflections
3240 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.134 w = 1/[σ2(Fo2) + (0.0702P)2 + 0.5073P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max = 0.001
3219 reflectionsΔρmax = 0.22 e Å3
242 parametersΔρmin = 0.25 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.019 (1)
Crystal data top
C24H22O2V = 1776.0 (3) Å3
Mr = 342.42Z = 4
Monoclinic, P21/cMo Kα radiation
a = 17.7903 (15) ŵ = 0.08 mm1
b = 5.5559 (5) ÅT = 293 K
c = 18.0320 (17) Å0.20 × 0.15 × 0.12 mm
β = 94.815 (8)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
2918 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968
Rint = 0.020
Tmin = 0.982, Tmax = 0.9943 standard reflections every 100 reflections
3351 measured reflections intensity decay: none
3240 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.134H-atom parameters constrained
S = 1.13Δρmax = 0.22 e Å3
3219 reflectionsΔρmin = 0.25 e Å3
242 parameters
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
C10.30720 (8)0.0597 (3)0.48337 (8)0.0359 (4)
C20.27564 (8)0.2219 (3)0.41991 (8)0.0339 (3)
C30.30985 (9)0.2620 (3)0.35436 (9)0.0437 (4)
H30.35440.18120.34680.0617 (17)*
C40.27952 (10)0.4186 (3)0.30020 (9)0.0471 (4)
H40.30380.44070.25700.0617 (17)*
C50.21325 (9)0.5433 (3)0.30951 (8)0.0418 (4)
C60.17752 (8)0.5000 (3)0.37371 (8)0.0382 (4)
H60.13210.57670.38040.0617 (17)*
C70.20853 (8)0.3442 (3)0.42792 (8)0.0336 (3)
O80.16857 (6)0.32295 (19)0.48966 (6)0.0415 (3)
C90.19234 (8)0.1556 (3)0.54748 (8)0.0338 (3)
O100.23546 (6)0.2869 (2)0.60392 (6)0.0463 (3)
C110.31112 (8)0.3243 (3)0.59697 (8)0.0364 (4)
C120.34644 (9)0.4796 (3)0.64909 (9)0.0423 (4)
H120.31890.54730.68540.0617 (17)*
C130.42220 (9)0.5352 (3)0.64765 (9)0.0430 (4)
C140.46228 (9)0.4236 (3)0.59462 (10)0.0454 (4)
H140.51360.45370.59370.0617 (17)*
C150.42673 (8)0.2679 (3)0.54305 (9)0.0412 (4)
H150.45490.19560.50800.0617 (17)*
C160.35004 (8)0.2165 (3)0.54211 (8)0.0348 (4)
C170.23897 (8)0.0455 (3)0.51835 (9)0.0377 (4)
H1710.20840.13790.48140.051 (4)*
H1720.25590.15260.55880.051 (4)*
C180.35545 (9)0.1458 (3)0.45674 (10)0.0472 (4)
H1810.32590.24100.42070.082 (2)*
H1820.37260.24500.49840.082 (2)*
H1830.39810.08050.43440.082 (2)*
C190.18166 (11)0.7257 (4)0.25354 (10)0.0554 (5)
H1910.12780.71060.24720.082 (2)*
H1920.20230.69810.20670.082 (2)*
H1930.19480.88470.27090.082 (2)*
C200.45821 (11)0.7212 (4)0.69991 (12)0.0596 (5)
H2010.44860.87880.67950.082 (2)*
H2020.51160.69400.70640.082 (2)*
H2030.43740.70940.74720.082 (2)*
C210.12048 (8)0.0820 (3)0.58102 (8)0.0359 (4)
C220.08950 (10)0.2302 (3)0.63167 (11)0.0517 (5)
H220.11420.37150.64700.0617 (17)*
C230.02198 (11)0.1707 (4)0.66000 (12)0.0626 (5)
H230.00160.27240.69400.0617 (17)*
C240.01511 (10)0.0378 (4)0.63817 (11)0.0562 (5)
H240.06030.07810.65750.0617 (17)*
C250.01504 (10)0.1851 (3)0.58797 (11)0.0546 (5)
H250.01010.32560.57270.0617 (17)*
C260.08279 (9)0.1281 (3)0.55926 (9)0.0470 (4)
H260.10290.23100.52540.0617 (17)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0327 (7)0.0310 (7)0.0439 (8)0.0035 (6)0.0028 (6)0.0024 (6)
C20.0319 (7)0.0323 (7)0.0374 (7)0.0012 (6)0.0019 (6)0.0063 (6)
C30.0406 (8)0.0480 (9)0.0436 (8)0.0020 (7)0.0096 (7)0.0078 (7)
C40.0516 (9)0.0557 (10)0.0350 (8)0.0058 (8)0.0103 (7)0.0039 (7)
C50.0424 (8)0.0469 (9)0.0352 (7)0.0080 (7)0.0023 (6)0.0011 (7)
C60.0314 (7)0.0401 (8)0.0425 (8)0.0012 (6)0.0001 (6)0.0021 (6)
C70.0321 (7)0.0334 (7)0.0355 (7)0.0027 (6)0.0037 (5)0.0016 (6)
O80.0408 (6)0.0414 (6)0.0443 (6)0.0123 (5)0.0148 (5)0.0114 (5)
C90.0324 (7)0.0316 (7)0.0372 (7)0.0013 (6)0.0018 (6)0.0011 (6)
O100.0316 (6)0.0605 (7)0.0475 (6)0.0079 (5)0.0068 (5)0.0177 (5)
C110.0306 (7)0.0388 (8)0.0395 (8)0.0001 (6)0.0007 (6)0.0016 (6)
C120.0405 (8)0.0462 (9)0.0399 (8)0.0013 (7)0.0012 (6)0.0030 (7)
C130.0385 (8)0.0418 (8)0.0465 (8)0.0031 (7)0.0087 (6)0.0030 (7)
C140.0295 (7)0.0473 (9)0.0582 (10)0.0001 (7)0.0027 (7)0.0043 (8)
C150.0310 (7)0.0404 (8)0.0519 (9)0.0043 (6)0.0026 (6)0.0007 (7)
C160.0314 (7)0.0319 (7)0.0405 (8)0.0034 (6)0.0002 (6)0.0034 (6)
C170.0349 (8)0.0309 (7)0.0470 (8)0.0006 (6)0.0027 (6)0.0017 (6)
C180.0421 (9)0.0370 (8)0.0632 (10)0.0082 (7)0.0076 (7)0.0077 (7)
C190.0569 (10)0.0658 (12)0.0426 (9)0.0064 (9)0.0019 (8)0.0134 (8)
C200.0494 (10)0.0597 (11)0.0670 (12)0.0081 (9)0.0107 (9)0.0090 (10)
C210.0320 (7)0.0377 (8)0.0376 (7)0.0001 (6)0.0003 (6)0.0078 (6)
C220.0417 (9)0.0482 (10)0.0672 (11)0.0045 (7)0.0154 (8)0.0083 (8)
C230.0465 (10)0.0710 (13)0.0735 (12)0.0008 (9)0.0238 (9)0.0105 (11)
C240.0360 (9)0.0668 (12)0.0670 (11)0.0045 (8)0.0117 (8)0.0142 (10)
C250.0434 (9)0.0539 (11)0.0665 (11)0.0141 (8)0.0045 (8)0.0056 (9)
C260.0426 (9)0.0485 (9)0.0503 (9)0.0083 (7)0.0059 (7)0.0024 (7)
Geometric parameters (Å, º) top
C1—C161.525 (2)C14—C151.383 (2)
C1—C21.526 (2)C14—H140.9300
C1—C181.530 (2)C15—C161.393 (2)
C1—C171.530 (2)C15—H150.9300
C2—C71.392 (2)C17—H1710.9700
C2—C31.392 (2)C17—H1720.9700
C3—C41.383 (2)C18—H1810.9600
C3—H30.9300C18—H1820.9600
C4—C51.390 (2)C18—H1830.9600
C4—H40.9300C19—H1910.9600
C5—C61.388 (2)C19—H1920.9600
C5—C191.505 (2)C19—H1930.9600
C6—C71.385 (2)C20—H2010.9600
C6—H60.9300C20—H2020.9600
C7—O81.3754 (17)C20—H2030.9600
O8—C91.4339 (17)C21—C221.379 (2)
C9—O101.4231 (17)C21—C261.386 (2)
C9—C171.512 (2)C22—C231.384 (2)
C9—C211.516 (2)C22—H220.9300
O10—C111.3780 (18)C23—C241.374 (3)
C11—C121.387 (2)C23—H230.9300
C11—C161.390 (2)C24—C251.363 (3)
C12—C131.385 (2)C24—H240.9300
C12—H120.9300C25—C261.388 (2)
C13—C141.386 (2)C25—H250.9300
C13—C201.505 (2)C26—H260.9300
C16—C1—C2108.34 (12)C16—C15—H15119.0
C16—C1—C18112.54 (12)C11—C16—C15116.67 (14)
C2—C1—C18112.72 (13)C11—C16—C1119.39 (13)
C16—C1—C17107.41 (12)C15—C16—C1123.90 (14)
C2—C1—C17106.27 (11)C9—C17—C1109.77 (12)
C18—C1—C17109.23 (13)C9—C17—H171109.7
C7—C2—C3116.75 (14)C1—C17—H171109.7
C7—C2—C1118.38 (13)C9—C17—H172109.7
C3—C2—C1124.86 (13)C1—C17—H172109.7
C4—C3—C2121.85 (15)H171—C17—H172108.2
C4—C3—H3119.1C1—C18—H182109.5
C2—C3—H3119.1C1—C18—H182109.5
C3—C4—C5120.85 (14)H181—C18—H182109.5
C3—C4—H4119.6C1—C18—H183109.5
C5—C4—H4119.6H181—C18—H183109.5
C6—C5—C4117.85 (15)H182—C18—H183109.5
C6—C5—C19120.30 (15)C5—C19—H191109.5
C4—C5—C19121.82 (15)C5—C19—H192109.5
C7—C6—C5120.91 (14)H191—C19—H192109.5
C7—C6—H6119.5C5—C19—H193109.5
C5—C6—H6119.5H191—C19—H193109.5
O8—C7—C6114.98 (12)H192—C19—H193109.5
O8—C7—C2123.26 (13)C13—C20—H201109.5
C6—C7—C2121.75 (13)C13—C20—H202109.5
C7—O8—C9120.20 (11)H201—C20—H202109.5
O10—C9—O8107.22 (12)C13—C20—H203109.5
O10—C9—C17110.40 (12)H201—C20—H203109.5
O8—C9—C17111.32 (12)H202—C20—H203109.5
O10—C9—C21105.96 (11)C22—C21—C26118.67 (15)
O8—C9—C21104.95 (11)C22—C21—C9120.05 (14)
C17—C9—C21116.43 (12)C26—C21—C9121.21 (14)
C11—O10—C9118.97 (11)C21—C22—C23120.60 (17)
O10—C11—C12115.00 (13)C21—C22—H22119.7
O10—C11—C16123.26 (13)C23—C22—H22119.7
C12—C11—C16121.74 (14)C24—C23—C22120.43 (18)
C13—C12—C11120.81 (15)C24—C23—H23119.8
C13—C12—H12119.6C22—C23—H23119.8
C11—C12—H12119.6C25—C24—C23119.34 (16)
C12—C13—C14118.09 (15)C25—C24—H24120.3
C12—C13—C20120.34 (16)C23—C24—H24120.3
C14—C13—C20121.50 (15)C24—C25—C26120.87 (17)
C15—C14—C13120.71 (15)C24—C25—H25119.6
C15—C14—H14119.6C26—C25—H25119.6
C13—C14—H14119.6C21—C26—C25120.08 (17)
C14—C15—C16121.92 (15)C21—C26—H26120.0
C14—C15—H15119.0C25—C26—H26120.0
C16—C1—C2—C781.93 (15)C20—C13—C14—C15174.62 (16)
C18—C1—C2—C7152.85 (14)C13—C14—C15—C160.1 (2)
C17—C1—C2—C733.23 (17)O10—C11—C16—C15178.76 (14)
C16—C1—C2—C396.63 (17)C12—C11—C16—C151.4 (2)
C18—C1—C2—C328.6 (2)O10—C11—C16—C13.7 (2)
C17—C1—C2—C3148.21 (14)C12—C11—C16—C1176.19 (14)
C7—C2—C3—C41.0 (2)C14—C15—C16—C111.7 (2)
C1—C2—C3—C4177.54 (14)C14—C15—C16—C1175.74 (14)
C2—C3—C4—C50.2 (3)C2—C1—C16—C1186.60 (16)
C3—C4—C5—C61.9 (2)C18—C1—C16—C11148.07 (14)
C3—C4—C5—C19176.24 (16)C17—C1—C16—C1127.81 (18)
C4—C5—C6—C72.3 (2)C2—C1—C16—C1590.79 (16)
C19—C5—C6—C7175.83 (15)C18—C1—C16—C1534.5 (2)
C5—C6—C7—O8178.16 (13)C17—C1—C16—C15154.80 (14)
C5—C6—C7—C21.1 (2)O10—C9—C17—C161.75 (15)
C3—C2—C7—O8179.81 (14)O8—C9—C17—C157.21 (15)
C1—C2—C7—O81.1 (2)C21—C9—C17—C1177.42 (11)
C3—C2—C7—C60.6 (2)C16—C1—C17—C955.57 (15)
C1—C2—C7—C6178.09 (13)C2—C1—C17—C960.21 (15)
C6—C7—O8—C9176.03 (12)C18—C1—C17—C9177.92 (12)
C2—C7—O8—C94.7 (2)O10—C9—C21—C2233.23 (19)
C7—O8—C9—O1097.08 (14)O8—C9—C21—C2280.03 (17)
C7—O8—C9—C1723.76 (17)C17—C9—C21—C22156.39 (15)
C7—O8—C9—C21150.54 (12)O10—C9—C21—C26149.75 (14)
O8—C9—O10—C1184.74 (15)O8—C9—C21—C2696.98 (16)
C17—C9—O10—C1136.68 (18)C17—C9—C21—C2626.6 (2)
C21—C9—O10—C11163.58 (13)C26—C21—C22—C230.2 (3)
C9—O10—C11—C12171.97 (13)C9—C21—C22—C23176.87 (16)
C9—O10—C11—C167.9 (2)C21—C22—C23—C240.2 (3)
O10—C11—C12—C13179.10 (15)C22—C23—C24—C250.4 (3)
C16—C11—C12—C130.8 (2)C23—C24—C25—C260.6 (3)
C11—C12—C13—C142.6 (2)C22—C21—C26—C250.4 (2)
C11—C12—C13—C20174.34 (15)C9—C21—C26—C25176.64 (15)
C12—C13—C14—C152.3 (2)C24—C25—C26—C210.6 (3)

Experimental details

Crystal data
Chemical formulaC24H22O2
Mr342.42
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)17.7903 (15), 5.5559 (5), 18.0320 (17)
β (°) 94.815 (8)
V3)1776.0 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.20 × 0.15 × 0.12
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968
Tmin, Tmax0.982, 0.994
No. of measured, independent and
observed [I > 2σ(I)] reflections
3351, 3240, 2918
Rint0.020
(sin θ/λ)max1)0.601
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.134, 1.13
No. of reflections3219
No. of parameters242
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.25

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), MolEN (Fair, 1990), MolEN, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolanai, 1997), SHELXL97 and PARST95 (Nardelli, 1995).

 

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