1,5,13-Trimethyl-9-phenyl-8,10-dioxatetracyclo[7.7.1.02,7.011,16]heptadeca-2,4,6,11,13,15-hexaene
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801001970/ci6004sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801001970/ci6004Isup2.hkl |
CCDC reference: 159845
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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).
All H atoms were fixed using geometrical considerations and their overall displacement parameters were refined.
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).
C24H22O2 | F(000) = 728 |
Mr = 342.42 | Dx = 1.281 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 17.7903 (15) Å | Cell parameters from 25 reflections |
b = 5.5559 (5) Å | θ = 2–25° |
c = 18.0320 (17) Å | µ = 0.08 mm−1 |
β = 94.815 (8)° | T = 293 K |
V = 1776.0 (3) Å3 | Needle, white |
Z = 4 | 0.20 × 0.15 × 0.12 mm |
Enraf-Nonius CAD-4 diffractometer | 2918 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 25.3°, θmin = 1.2° |
ω–2θ scans | h = 0→21 |
Absorption correction: ψ scan (North et al., 1968 | k = 0→6 |
Tmin = 0.982, Tmax = 0.994 | l = −21→21 |
3351 measured reflections | 3 standard reflections every 100 reflections |
3240 independent reflections | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H-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 reflections | Δρmax = 0.22 e Å−3 |
242 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.019 (1) |
C24H22O2 | V = 1776.0 (3) Å3 |
Mr = 342.42 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 17.7903 (15) Å | µ = 0.08 mm−1 |
b = 5.5559 (5) Å | T = 293 K |
c = 18.0320 (17) Å | 0.20 × 0.15 × 0.12 mm |
β = 94.815 (8)° |
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 = 0.994 | 3 standard reflections every 100 reflections |
3351 measured reflections | intensity decay: none |
3240 independent reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.13 | Δρmax = 0.22 e Å−3 |
3219 reflections | Δρmin = −0.25 e Å−3 |
242 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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.30720 (8) | 0.0597 (3) | 0.48337 (8) | 0.0359 (4) | |
C2 | 0.27564 (8) | 0.2219 (3) | 0.41991 (8) | 0.0339 (3) | |
C3 | 0.30985 (9) | 0.2620 (3) | 0.35436 (9) | 0.0437 (4) | |
H3 | 0.3544 | 0.1812 | 0.3468 | 0.0617 (17)* | |
C4 | 0.27952 (10) | 0.4186 (3) | 0.30020 (9) | 0.0471 (4) | |
H4 | 0.3038 | 0.4407 | 0.2570 | 0.0617 (17)* | |
C5 | 0.21325 (9) | 0.5433 (3) | 0.30951 (8) | 0.0418 (4) | |
C6 | 0.17752 (8) | 0.5000 (3) | 0.37371 (8) | 0.0382 (4) | |
H6 | 0.1321 | 0.5767 | 0.3804 | 0.0617 (17)* | |
C7 | 0.20853 (8) | 0.3442 (3) | 0.42792 (8) | 0.0336 (3) | |
O8 | 0.16857 (6) | 0.32295 (19) | 0.48966 (6) | 0.0415 (3) | |
C9 | 0.19234 (8) | 0.1556 (3) | 0.54748 (8) | 0.0338 (3) | |
O10 | 0.23546 (6) | 0.2869 (2) | 0.60392 (6) | 0.0463 (3) | |
C11 | 0.31112 (8) | 0.3243 (3) | 0.59697 (8) | 0.0364 (4) | |
C12 | 0.34644 (9) | 0.4796 (3) | 0.64909 (9) | 0.0423 (4) | |
H12 | 0.3189 | 0.5473 | 0.6854 | 0.0617 (17)* | |
C13 | 0.42220 (9) | 0.5352 (3) | 0.64765 (9) | 0.0430 (4) | |
C14 | 0.46228 (9) | 0.4236 (3) | 0.59462 (10) | 0.0454 (4) | |
H14 | 0.5136 | 0.4537 | 0.5937 | 0.0617 (17)* | |
C15 | 0.42673 (8) | 0.2679 (3) | 0.54305 (9) | 0.0412 (4) | |
H15 | 0.4549 | 0.1956 | 0.5080 | 0.0617 (17)* | |
C16 | 0.35004 (8) | 0.2165 (3) | 0.54211 (8) | 0.0348 (4) | |
C17 | 0.23897 (8) | −0.0455 (3) | 0.51835 (9) | 0.0377 (4) | |
H171 | 0.2084 | −0.1379 | 0.4814 | 0.051 (4)* | |
H172 | 0.2559 | −0.1526 | 0.5588 | 0.051 (4)* | |
C18 | 0.35545 (9) | −0.1458 (3) | 0.45674 (10) | 0.0472 (4) | |
H181 | 0.3259 | −0.2410 | 0.4207 | 0.082 (2)* | |
H182 | 0.3726 | −0.2450 | 0.4984 | 0.082 (2)* | |
H183 | 0.3981 | −0.0805 | 0.4344 | 0.082 (2)* | |
C19 | 0.18166 (11) | 0.7257 (4) | 0.25354 (10) | 0.0554 (5) | |
H191 | 0.1278 | 0.7106 | 0.2472 | 0.082 (2)* | |
H192 | 0.2023 | 0.6981 | 0.2067 | 0.082 (2)* | |
H193 | 0.1948 | 0.8847 | 0.2709 | 0.082 (2)* | |
C20 | 0.45821 (11) | 0.7212 (4) | 0.69991 (12) | 0.0596 (5) | |
H201 | 0.4486 | 0.8788 | 0.6795 | 0.082 (2)* | |
H202 | 0.5116 | 0.6940 | 0.7064 | 0.082 (2)* | |
H203 | 0.4374 | 0.7094 | 0.7472 | 0.082 (2)* | |
C21 | 0.12048 (8) | 0.0820 (3) | 0.58102 (8) | 0.0359 (4) | |
C22 | 0.08950 (10) | 0.2302 (3) | 0.63167 (11) | 0.0517 (5) | |
H22 | 0.1142 | 0.3715 | 0.6470 | 0.0617 (17)* | |
C23 | 0.02198 (11) | 0.1707 (4) | 0.66000 (12) | 0.0626 (5) | |
H23 | 0.0016 | 0.2724 | 0.6940 | 0.0617 (17)* | |
C24 | −0.01511 (10) | −0.0378 (4) | 0.63817 (11) | 0.0562 (5) | |
H24 | −0.0603 | −0.0781 | 0.6575 | 0.0617 (17)* | |
C25 | 0.01504 (10) | −0.1851 (3) | 0.58797 (11) | 0.0546 (5) | |
H25 | −0.0101 | −0.3256 | 0.5727 | 0.0617 (17)* | |
C26 | 0.08279 (9) | −0.1281 (3) | 0.55926 (9) | 0.0470 (4) | |
H26 | 0.1029 | −0.2310 | 0.5254 | 0.0617 (17)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0327 (7) | 0.0310 (7) | 0.0439 (8) | 0.0035 (6) | 0.0028 (6) | −0.0024 (6) |
C2 | 0.0319 (7) | 0.0323 (7) | 0.0374 (7) | −0.0012 (6) | 0.0019 (6) | −0.0063 (6) |
C3 | 0.0406 (8) | 0.0480 (9) | 0.0436 (8) | 0.0020 (7) | 0.0096 (7) | −0.0078 (7) |
C4 | 0.0516 (9) | 0.0557 (10) | 0.0350 (8) | −0.0058 (8) | 0.0103 (7) | −0.0039 (7) |
C5 | 0.0424 (8) | 0.0469 (9) | 0.0352 (7) | −0.0080 (7) | −0.0023 (6) | 0.0011 (7) |
C6 | 0.0314 (7) | 0.0401 (8) | 0.0425 (8) | −0.0012 (6) | 0.0001 (6) | 0.0021 (6) |
C7 | 0.0321 (7) | 0.0334 (7) | 0.0355 (7) | −0.0027 (6) | 0.0037 (5) | −0.0016 (6) |
O8 | 0.0408 (6) | 0.0414 (6) | 0.0443 (6) | 0.0123 (5) | 0.0148 (5) | 0.0114 (5) |
C9 | 0.0324 (7) | 0.0316 (7) | 0.0372 (7) | −0.0013 (6) | 0.0018 (6) | 0.0011 (6) |
O10 | 0.0316 (6) | 0.0605 (7) | 0.0475 (6) | −0.0079 (5) | 0.0068 (5) | −0.0177 (5) |
C11 | 0.0306 (7) | 0.0388 (8) | 0.0395 (8) | −0.0001 (6) | 0.0007 (6) | 0.0016 (6) |
C12 | 0.0405 (8) | 0.0462 (9) | 0.0399 (8) | −0.0013 (7) | 0.0012 (6) | −0.0030 (7) |
C13 | 0.0385 (8) | 0.0418 (8) | 0.0465 (8) | −0.0031 (7) | −0.0087 (6) | 0.0030 (7) |
C14 | 0.0295 (7) | 0.0473 (9) | 0.0582 (10) | −0.0001 (7) | −0.0027 (7) | 0.0043 (8) |
C15 | 0.0310 (7) | 0.0404 (8) | 0.0519 (9) | 0.0043 (6) | 0.0026 (6) | 0.0007 (7) |
C16 | 0.0314 (7) | 0.0319 (7) | 0.0405 (8) | 0.0034 (6) | 0.0002 (6) | 0.0034 (6) |
C17 | 0.0349 (8) | 0.0309 (7) | 0.0470 (8) | 0.0006 (6) | 0.0027 (6) | 0.0017 (6) |
C18 | 0.0421 (9) | 0.0370 (8) | 0.0632 (10) | 0.0082 (7) | 0.0076 (7) | −0.0077 (7) |
C19 | 0.0569 (10) | 0.0658 (12) | 0.0426 (9) | −0.0064 (9) | −0.0019 (8) | 0.0134 (8) |
C20 | 0.0494 (10) | 0.0597 (11) | 0.0670 (12) | −0.0081 (9) | −0.0107 (9) | −0.0090 (10) |
C21 | 0.0320 (7) | 0.0377 (8) | 0.0376 (7) | −0.0001 (6) | 0.0003 (6) | 0.0078 (6) |
C22 | 0.0417 (9) | 0.0482 (10) | 0.0672 (11) | −0.0045 (7) | 0.0154 (8) | −0.0083 (8) |
C23 | 0.0465 (10) | 0.0710 (13) | 0.0735 (12) | −0.0008 (9) | 0.0238 (9) | −0.0105 (11) |
C24 | 0.0360 (9) | 0.0668 (12) | 0.0670 (11) | −0.0045 (8) | 0.0117 (8) | 0.0142 (10) |
C25 | 0.0434 (9) | 0.0539 (11) | 0.0665 (11) | −0.0141 (8) | 0.0045 (8) | 0.0056 (9) |
C26 | 0.0426 (9) | 0.0485 (9) | 0.0503 (9) | −0.0083 (7) | 0.0059 (7) | −0.0024 (7) |
C1—C16 | 1.525 (2) | C14—C15 | 1.383 (2) |
C1—C2 | 1.526 (2) | C14—H14 | 0.9300 |
C1—C18 | 1.530 (2) | C15—C16 | 1.393 (2) |
C1—C17 | 1.530 (2) | C15—H15 | 0.9300 |
C2—C7 | 1.392 (2) | C17—H171 | 0.9700 |
C2—C3 | 1.392 (2) | C17—H172 | 0.9700 |
C3—C4 | 1.383 (2) | C18—H181 | 0.9600 |
C3—H3 | 0.9300 | C18—H182 | 0.9600 |
C4—C5 | 1.390 (2) | C18—H183 | 0.9600 |
C4—H4 | 0.9300 | C19—H191 | 0.9600 |
C5—C6 | 1.388 (2) | C19—H192 | 0.9600 |
C5—C19 | 1.505 (2) | C19—H193 | 0.9600 |
C6—C7 | 1.385 (2) | C20—H201 | 0.9600 |
C6—H6 | 0.9300 | C20—H202 | 0.9600 |
C7—O8 | 1.3754 (17) | C20—H203 | 0.9600 |
O8—C9 | 1.4339 (17) | C21—C22 | 1.379 (2) |
C9—O10 | 1.4231 (17) | C21—C26 | 1.386 (2) |
C9—C17 | 1.512 (2) | C22—C23 | 1.384 (2) |
C9—C21 | 1.516 (2) | C22—H22 | 0.9300 |
O10—C11 | 1.3780 (18) | C23—C24 | 1.374 (3) |
C11—C12 | 1.387 (2) | C23—H23 | 0.9300 |
C11—C16 | 1.390 (2) | C24—C25 | 1.363 (3) |
C12—C13 | 1.385 (2) | C24—H24 | 0.9300 |
C12—H12 | 0.9300 | C25—C26 | 1.388 (2) |
C13—C14 | 1.386 (2) | C25—H25 | 0.9300 |
C13—C20 | 1.505 (2) | C26—H26 | 0.9300 |
C16—C1—C2 | 108.34 (12) | C16—C15—H15 | 119.0 |
C16—C1—C18 | 112.54 (12) | C11—C16—C15 | 116.67 (14) |
C2—C1—C18 | 112.72 (13) | C11—C16—C1 | 119.39 (13) |
C16—C1—C17 | 107.41 (12) | C15—C16—C1 | 123.90 (14) |
C2—C1—C17 | 106.27 (11) | C9—C17—C1 | 109.77 (12) |
C18—C1—C17 | 109.23 (13) | C9—C17—H171 | 109.7 |
C7—C2—C3 | 116.75 (14) | C1—C17—H171 | 109.7 |
C7—C2—C1 | 118.38 (13) | C9—C17—H172 | 109.7 |
C3—C2—C1 | 124.86 (13) | C1—C17—H172 | 109.7 |
C4—C3—C2 | 121.85 (15) | H171—C17—H172 | 108.2 |
C4—C3—H3 | 119.1 | C1—C18—H182 | 109.5 |
C2—C3—H3 | 119.1 | C1—C18—H182 | 109.5 |
C3—C4—C5 | 120.85 (14) | H181—C18—H182 | 109.5 |
C3—C4—H4 | 119.6 | C1—C18—H183 | 109.5 |
C5—C4—H4 | 119.6 | H181—C18—H183 | 109.5 |
C6—C5—C4 | 117.85 (15) | H182—C18—H183 | 109.5 |
C6—C5—C19 | 120.30 (15) | C5—C19—H191 | 109.5 |
C4—C5—C19 | 121.82 (15) | C5—C19—H192 | 109.5 |
C7—C6—C5 | 120.91 (14) | H191—C19—H192 | 109.5 |
C7—C6—H6 | 119.5 | C5—C19—H193 | 109.5 |
C5—C6—H6 | 119.5 | H191—C19—H193 | 109.5 |
O8—C7—C6 | 114.98 (12) | H192—C19—H193 | 109.5 |
O8—C7—C2 | 123.26 (13) | C13—C20—H201 | 109.5 |
C6—C7—C2 | 121.75 (13) | C13—C20—H202 | 109.5 |
C7—O8—C9 | 120.20 (11) | H201—C20—H202 | 109.5 |
O10—C9—O8 | 107.22 (12) | C13—C20—H203 | 109.5 |
O10—C9—C17 | 110.40 (12) | H201—C20—H203 | 109.5 |
O8—C9—C17 | 111.32 (12) | H202—C20—H203 | 109.5 |
O10—C9—C21 | 105.96 (11) | C22—C21—C26 | 118.67 (15) |
O8—C9—C21 | 104.95 (11) | C22—C21—C9 | 120.05 (14) |
C17—C9—C21 | 116.43 (12) | C26—C21—C9 | 121.21 (14) |
C11—O10—C9 | 118.97 (11) | C21—C22—C23 | 120.60 (17) |
O10—C11—C12 | 115.00 (13) | C21—C22—H22 | 119.7 |
O10—C11—C16 | 123.26 (13) | C23—C22—H22 | 119.7 |
C12—C11—C16 | 121.74 (14) | C24—C23—C22 | 120.43 (18) |
C13—C12—C11 | 120.81 (15) | C24—C23—H23 | 119.8 |
C13—C12—H12 | 119.6 | C22—C23—H23 | 119.8 |
C11—C12—H12 | 119.6 | C25—C24—C23 | 119.34 (16) |
C12—C13—C14 | 118.09 (15) | C25—C24—H24 | 120.3 |
C12—C13—C20 | 120.34 (16) | C23—C24—H24 | 120.3 |
C14—C13—C20 | 121.50 (15) | C24—C25—C26 | 120.87 (17) |
C15—C14—C13 | 120.71 (15) | C24—C25—H25 | 119.6 |
C15—C14—H14 | 119.6 | C26—C25—H25 | 119.6 |
C13—C14—H14 | 119.6 | C21—C26—C25 | 120.08 (17) |
C14—C15—C16 | 121.92 (15) | C21—C26—H26 | 120.0 |
C14—C15—H15 | 119.0 | C25—C26—H26 | 120.0 |
C16—C1—C2—C7 | −81.93 (15) | C20—C13—C14—C15 | −174.62 (16) |
C18—C1—C2—C7 | 152.85 (14) | C13—C14—C15—C16 | −0.1 (2) |
C17—C1—C2—C7 | 33.23 (17) | O10—C11—C16—C15 | −178.76 (14) |
C16—C1—C2—C3 | 96.63 (17) | C12—C11—C16—C15 | 1.4 (2) |
C18—C1—C2—C3 | −28.6 (2) | O10—C11—C16—C1 | 3.7 (2) |
C17—C1—C2—C3 | −148.21 (14) | C12—C11—C16—C1 | −176.19 (14) |
C7—C2—C3—C4 | 1.0 (2) | C14—C15—C16—C11 | −1.7 (2) |
C1—C2—C3—C4 | −177.54 (14) | C14—C15—C16—C1 | 175.74 (14) |
C2—C3—C4—C5 | 0.2 (3) | C2—C1—C16—C11 | 86.60 (16) |
C3—C4—C5—C6 | −1.9 (2) | C18—C1—C16—C11 | −148.07 (14) |
C3—C4—C5—C19 | 176.24 (16) | C17—C1—C16—C11 | −27.81 (18) |
C4—C5—C6—C7 | 2.3 (2) | C2—C1—C16—C15 | −90.79 (16) |
C19—C5—C6—C7 | −175.83 (15) | C18—C1—C16—C15 | 34.5 (2) |
C5—C6—C7—O8 | 178.16 (13) | C17—C1—C16—C15 | 154.80 (14) |
C5—C6—C7—C2 | −1.1 (2) | O10—C9—C17—C1 | −61.75 (15) |
C3—C2—C7—O8 | −179.81 (14) | O8—C9—C17—C1 | 57.21 (15) |
C1—C2—C7—O8 | −1.1 (2) | C21—C9—C17—C1 | 177.42 (11) |
C3—C2—C7—C6 | −0.6 (2) | C16—C1—C17—C9 | 55.57 (15) |
C1—C2—C7—C6 | 178.09 (13) | C2—C1—C17—C9 | −60.21 (15) |
C6—C7—O8—C9 | 176.03 (12) | C18—C1—C17—C9 | 177.92 (12) |
C2—C7—O8—C9 | −4.7 (2) | O10—C9—C21—C22 | 33.23 (19) |
C7—O8—C9—O10 | 97.08 (14) | O8—C9—C21—C22 | −80.03 (17) |
C7—O8—C9—C17 | −23.76 (17) | C17—C9—C21—C22 | 156.39 (15) |
C7—O8—C9—C21 | −150.54 (12) | O10—C9—C21—C26 | −149.75 (14) |
O8—C9—O10—C11 | −84.74 (15) | O8—C9—C21—C26 | 96.98 (16) |
C17—C9—O10—C11 | 36.68 (18) | C17—C9—C21—C26 | −26.6 (2) |
C21—C9—O10—C11 | 163.58 (13) | C26—C21—C22—C23 | −0.2 (3) |
C9—O10—C11—C12 | 171.97 (13) | C9—C21—C22—C23 | 176.87 (16) |
C9—O10—C11—C16 | −7.9 (2) | C21—C22—C23—C24 | 0.2 (3) |
O10—C11—C12—C13 | −179.10 (15) | C22—C23—C24—C25 | −0.4 (3) |
C16—C11—C12—C13 | 0.8 (2) | C23—C24—C25—C26 | 0.6 (3) |
C11—C12—C13—C14 | −2.6 (2) | C22—C21—C26—C25 | 0.4 (2) |
C11—C12—C13—C20 | 174.34 (15) | C9—C21—C26—C25 | −176.64 (15) |
C12—C13—C14—C15 | 2.3 (2) | C24—C25—C26—C21 | −0.6 (3) |
Experimental details
Crystal data | |
Chemical formula | C24H22O2 |
Mr | 342.42 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 17.7903 (15), 5.5559 (5), 18.0320 (17) |
β (°) | 94.815 (8) |
V (Å3) | 1776.0 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.20 × 0.15 × 0.12 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968 |
Tmin, Tmax | 0.982, 0.994 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3351, 3240, 2918 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.601 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.134, 1.13 |
No. of reflections | 3219 |
No. of parameters | 242 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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).
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°].