organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(2E)-4-tert-Butyl-2-(4-meth­­oxy­benzyl­­idene)-3,4-di­hydro­naphthalen-1(2H)-one

aLaboratoire de Chimie Organique, Faculté des Sciences Dhar el Mahraz, Université Sidi Mohammed Ben Abdellah, Fès, Morocco, and bLaboratoire de Diffraction des Rayons X, Centre National pour la Recherche Scientifique et Technique, Rabat, Morocco
*Correspondence e-mail: makhazzane@yahoo.com

(Received 25 May 2011; accepted 7 June 2011; online 25 June 2011)

In the title compound C22H24O2, the exocyclic C=C double bond is in an E configuration and the tert-butyl group is in an axial position on the cyclo­hexa­none ring. The cyclo­hexa­none ring in the dihydro­naphthalene fused-ring system adopts a half-chair conformation in both independent two mol­ecules in the asymetric unit. The benzene ring system is oriented angles of 43.97 (12) and 39.24 (12)° with respect to the naphthyl ring system in the two independent mol­ecules. In the crystal, mol­ecules are linked via C—H⋯O hydrogen bonds and C—H⋯π inter­actions.

Related literature

For general background to dipolar 1,3-cyclo­addition reactions, see: Bennani et al. (2007[Bennani, B., Kerbal, A., Daoudi, M., Filali Baba, B., Al Houari, G., Jalbout, A. F., Mimouni, M., Benazza, M., Demailly, G., Akkurt, M., Öztürk Yıldırım, S. & Ben Hadda, T. (2007). ARKIVOC, xvi, 19-40.]); Kerbal et al. (1988[Kerbal, A., Tshiamala, K., Vebrel, J. & Laude, B. (1988). Bull. Soc. Chim. Belg. 97, 149-161.]); Al Houari et al. (2008[Al Houari, G., Kerbal, A., Bennani, B., Baba, M. F., Daoudi, M. & Ben Hadda, T. (2008). ARKIVOC, xii, 42-50,]). For a related structure, see: Akhazzane et al. (2010[Akhazzane, M., Zouihri, H., Daran, J.-C., Kerbal, A. & Al Houari, G. (2010). Acta Cryst. E66, o3067.]). For conformation analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358;]).

[Scheme 1]

Experimental

Crystal data
  • C22H24O2

  • Mr = 320.41

  • Orthorhombic, P c a 21

  • a = 11.2265 (2) Å

  • b = 21.7630 (5) Å

  • c = 14.8001 (4) Å

  • V = 3615.99 (14) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 296 K

  • 0.24 × 0.17 × 0.16 mm

Data collection
  • Bruker APEXII CCD detector diffractometer

  • 20114 measured reflections

  • 6654 independent reflections

  • 4552 reflections with I > 2σ(I)

  • Rint = 0.033

Refinement
  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 0.147

  • S = 1.03

  • 6654 reflections

  • 441 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.41 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 and Cg7 are the centroids of the C111–C116 and C211–C216 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C104—H104⋯O21i 0.93 2.53 3.439 (3) 167
C121—H12DCg7 0.96 2.92 3.801 (4) 153
C221—H22FCg3 0.96 2.86 3.686 (4) 144
Symmetry code: (i) [x+{\script{1\over 2}}, -y+1, z].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Knowledge of the configuration and conformation of the title compound is necessary to understand its behaviour in dipolar-1,3 cycloaddition reactions [Bennani, et al. (2007) and Al Houari et al. (2008)]. To confirm the E configuration of the exocyclic C=C double bond, an X-ray crystal structure determination has been carried out.

In the title compound, as shown in Fig. 1, all bond lengths and angles are normal and comparable with those reported for the related structure [Akhazzane et al., (2010)].

The asymmetric unit cell contains two molecules (Fig.1). The cyclohexanone ring in the dihydronaphthalin ring system has a half-chair conformation, presumably due to conjugation of the planar annulated benzo ring, with the puckering parameters of: Q(2) = 0.419 (3) Å, ϕ(2) = 148.0 (4)°, Q(3) = 0.189 (3) Å and: Q(2) = 0.410 (3) Å., ϕ(2) = 89.4 (4) °, Q(3) = 0.192 (3) Å in the two independent molecules, respectivly. (Cremer & Pople, 1975).

In the crystal, molecules are linked via C—H···O hydrogen bonds (Table. 1). The crystal structure is further stablized by intermolecular C—H···π interactions between the methyl of the methoxybenzene and the neighboring benzene ring.

Related literature top

For general background to dipolar 1,3-cycloaddition reactions, see: Bennani et al. (2007); Kerbal et al. (1988); Al Houari et al. (2008). For a related structure, see: Akhazzane et al. (2010). For conformation analysis, see: Cremer & Pople (1975).

Experimental top

The synthesis of 2-(4-methoxybenzylidene)-4-tertiobutyl-3,4-dihydronaphthalen-1(2H)-one was achieved using the method reported by [Kerbal et al. (1988)]. i.e. by a condensation of para anisaldehyde with 4-tertiobutyl-3,4-dihydronaphthalen-1(2H)-one in an alkaline medium in methanol.

Refinement top

The H atoms bound to C were treated as riding with their parent atoms [C—H distances are 0.93Å for CH groups with Uiso(H) = 1.2 Ueq(C), and 0.97 Å for CH3 groups with Uiso(H) = 1.5 Ueq(C)].

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Molecular view of the title compound showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
(2E)-4-tert-butyl-2-(4-methoxybenzylidene)-3,4- dihydronaphthalen-1(2H)-one top
Crystal data top
C22H24O2F(000) = 1376
Mr = 320.41Dx = 1.177 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 256 reflections
a = 11.2265 (2) Åθ = 2.4–25.8°
b = 21.7630 (5) ŵ = 0.07 mm1
c = 14.8001 (4) ÅT = 296 K
V = 3615.99 (14) Å3Prism, colourless
Z = 80.24 × 0.17 × 0.16 mm
Data collection top
Bruker APEXII CCD detector
diffractometer
4552 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
Graphite monochromatorθmax = 26.5°, θmin = 0.9°
ω and ϕ scansh = 1314
20114 measured reflectionsk = 2427
6654 independent reflectionsl = 1618
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.088P)2]
where P = (Fo2 + 2Fc2)/3
6654 reflections(Δ/σ)max = 0.011
441 parametersΔρmax = 0.41 e Å3
1 restraintΔρmin = 0.21 e Å3
Crystal data top
C22H24O2V = 3615.99 (14) Å3
Mr = 320.41Z = 8
Orthorhombic, Pca21Mo Kα radiation
a = 11.2265 (2) ŵ = 0.07 mm1
b = 21.7630 (5) ÅT = 296 K
c = 14.8001 (4) Å0.24 × 0.17 × 0.16 mm
Data collection top
Bruker APEXII CCD detector
diffractometer
4552 reflections with I > 2σ(I)
20114 measured reflectionsRint = 0.033
6654 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0561 restraint
wR(F2) = 0.147H-atom parameters constrained
S = 1.03Δρmax = 0.41 e Å3
6654 reflectionsΔρmin = 0.21 e Å3
441 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
C1000.6470 (2)0.38382 (11)0.4388 (2)0.0411 (6)
C1010.6110 (2)0.33059 (12)0.4851 (2)0.0532 (7)
C1020.6531 (3)0.27392 (13)0.4598 (3)0.0622 (8)
C1030.7326 (3)0.26978 (13)0.3892 (3)0.0641 (9)
C1040.7685 (2)0.32188 (12)0.3434 (2)0.0552 (7)
C1050.7248 (2)0.38008 (11)0.36673 (19)0.0424 (6)
C1060.7596 (2)0.43672 (10)0.31438 (19)0.0415 (6)
C1070.7704 (3)0.49220 (11)0.3798 (2)0.0429 (7)
C1080.6628 (2)0.50071 (10)0.4383 (2)0.0403 (7)
C1090.5989 (2)0.44403 (12)0.4701 (2)0.0440 (7)
C1100.6144 (2)0.55490 (11)0.4650 (2)0.0444 (7)
C1110.6550 (2)0.61823 (12)0.4470 (2)0.0439 (7)
C1120.7729 (2)0.63626 (11)0.4354 (2)0.0534 (8)
C1130.8008 (2)0.69646 (12)0.4200 (2)0.0605 (8)
C1140.7139 (3)0.74091 (12)0.4167 (2)0.0531 (8)
C1150.5966 (3)0.72479 (12)0.4296 (2)0.0577 (8)
C1160.5687 (3)0.66397 (12)0.4458 (2)0.0583 (8)
C1170.6807 (2)0.44838 (12)0.22824 (19)0.0475 (7)
C1180.6908 (3)0.39284 (16)0.1651 (2)0.0806 (10)
C1190.7281 (4)0.50413 (15)0.1770 (3)0.0739 (12)
C1200.5498 (2)0.45874 (18)0.2510 (3)0.0786 (11)
C1210.6667 (3)0.84831 (13)0.4022 (3)0.0801 (11)
C2010.6361 (3)1.16663 (12)0.0896 (2)0.0603 (8)
C2020.5944 (3)1.22365 (14)0.1102 (3)0.0714 (10)
C2030.5132 (3)1.23039 (13)0.1791 (3)0.0699 (11)
C2040.4739 (2)1.17962 (12)0.2283 (2)0.0579 (8)
C2050.5184 (2)1.12162 (11)0.20951 (19)0.0426 (6)
C2060.4829 (2)1.06589 (11)0.26467 (19)0.0407 (6)
C2070.4753 (3)1.00980 (13)0.2027 (2)0.0438 (7)
C2080.5855 (2)0.99897 (10)0.1451 (2)0.0378 (7)
C2090.6456 (2)1.05429 (12)0.1115 (2)0.0437 (7)
C2100.6308 (2)0.94469 (11)0.1232 (2)0.0442 (7)
C2110.5944 (2)0.88216 (12)0.1428 (2)0.0428 (7)
C2120.4772 (2)0.86312 (12)0.1611 (2)0.0476 (7)
C2130.4502 (2)0.80294 (11)0.1798 (2)0.0504 (7)
C2140.5383 (3)0.75867 (12)0.1790 (2)0.0496 (8)
C2150.6544 (2)0.77552 (12)0.1599 (2)0.0589 (8)
C2160.6790 (2)0.83588 (12)0.1417 (2)0.0547 (7)
C2170.5618 (2)1.05718 (11)0.3510 (2)0.0452 (6)
C2180.5489 (3)1.11228 (14)0.4134 (2)0.0682 (9)
C2190.5204 (5)1.00059 (14)0.4031 (3)0.0789 (13)
C2200.6944 (2)1.04974 (16)0.3289 (2)0.0761 (11)
C2210.5906 (3)0.65256 (12)0.1973 (3)0.0718 (9)
C2220.5994 (2)1.11478 (12)0.1365 (2)0.0406 (7)
H1010.55830.33380.53330.064*
H1020.62810.23870.49000.075*
H1030.76240.23160.37220.077*
H1040.82280.31830.29620.066*
H1060.84030.42900.29190.050*
H10A0.83960.48630.41810.052*
H10B0.78310.52930.34480.052*
H1100.54560.55170.49980.053*
H1120.83330.60710.43810.064*
H1130.88000.70760.41160.073*
H1150.53700.75440.42740.069*
H1160.48970.65330.45630.070*
H11A0.80920.49680.15940.111*
H11B0.72450.53970.21520.111*
H11C0.68040.51090.12410.111*
H11D0.65210.40190.10880.121*
H11E0.65320.35790.19260.121*
H11F0.77330.38380.15430.121*
H12A0.50660.46790.19670.118*
H12B0.54280.49250.29240.118*
H12C0.51770.42230.27830.118*
H12D0.61480.84420.35100.120*
H12E0.70720.88710.39920.120*
H12F0.62070.84630.45680.120*
H2010.69081.16230.04280.072*
H2020.62051.25780.07790.086*
H2030.48431.26930.19310.084*
H2040.41761.18470.27390.070*
H2060.40181.07370.28620.049*
H20A0.46150.97360.23950.053*
H20B0.40711.01470.16310.053*
H2100.69960.94720.08840.053*
H2120.41630.89210.16060.057*
H2130.37210.79190.19310.060*
H2150.71480.74630.15950.071*
H2160.75720.84640.12770.066*
H21A0.59701.10620.46620.102*
H21B0.46691.11670.43090.102*
H21C0.57441.14870.38240.102*
H21D0.56080.99880.46020.118*
H21E0.53820.96430.36880.118*
H21F0.43601.00310.41310.118*
H22A0.72131.08470.29500.114*
H22B0.70591.01310.29370.114*
H22C0.73911.04670.38400.114*
H22D0.62870.65070.13940.108*
H22E0.55340.61380.21010.108*
H22F0.64890.66140.24300.108*
O100.51340 (18)0.44643 (8)0.52145 (17)0.0632 (6)
O110.7524 (2)0.79948 (8)0.40158 (18)0.0742 (7)
O200.73570 (19)1.05053 (8)0.06354 (16)0.0657 (6)
O210.50231 (18)0.69992 (8)0.19669 (16)0.0639 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1000.0373 (14)0.0491 (15)0.0369 (16)0.0045 (12)0.0024 (13)0.0011 (13)
C1010.0571 (17)0.0589 (17)0.0436 (18)0.0105 (13)0.0010 (14)0.0046 (14)
C1020.074 (2)0.0477 (16)0.065 (2)0.0026 (14)0.0001 (17)0.0072 (15)
C1030.070 (2)0.0445 (15)0.078 (3)0.0091 (16)0.0053 (19)0.0052 (16)
C1040.0481 (16)0.0600 (16)0.058 (2)0.0076 (13)0.0010 (14)0.0029 (15)
C1050.0349 (14)0.0490 (13)0.0433 (17)0.0012 (11)0.0073 (12)0.0024 (12)
C1060.0301 (12)0.0516 (14)0.0429 (16)0.0020 (11)0.0038 (11)0.0047 (12)
C1070.0359 (15)0.0509 (14)0.0420 (19)0.0005 (11)0.0009 (13)0.0037 (13)
C1080.0369 (17)0.0494 (18)0.0347 (18)0.0027 (10)0.0020 (16)0.0018 (10)
C1090.0373 (16)0.0582 (17)0.0366 (18)0.0070 (12)0.0006 (14)0.0034 (13)
C1100.0425 (16)0.0555 (17)0.0353 (18)0.0003 (12)0.0009 (13)0.0046 (13)
C1110.0478 (17)0.0484 (15)0.0356 (17)0.0019 (13)0.0002 (14)0.0067 (13)
C1120.0429 (16)0.0490 (15)0.068 (2)0.0053 (12)0.0141 (14)0.0067 (14)
C1130.0430 (16)0.0589 (17)0.079 (2)0.0047 (13)0.0091 (15)0.0010 (16)
C1140.057 (2)0.0472 (15)0.056 (2)0.0006 (13)0.0072 (15)0.0006 (14)
C1150.0543 (18)0.0510 (16)0.068 (2)0.0108 (13)0.0060 (15)0.0006 (15)
C1160.0471 (17)0.0599 (17)0.068 (2)0.0043 (13)0.0112 (15)0.0004 (16)
C1170.0410 (14)0.0669 (16)0.0345 (15)0.0031 (12)0.0009 (11)0.0042 (13)
C1180.100 (3)0.094 (2)0.049 (2)0.008 (2)0.0109 (19)0.0183 (19)
C1190.070 (3)0.097 (3)0.055 (3)0.0033 (16)0.002 (2)0.0214 (18)
C1200.0443 (17)0.143 (3)0.049 (2)0.0093 (18)0.0089 (15)0.005 (2)
C1210.089 (2)0.0523 (17)0.099 (3)0.0078 (16)0.002 (2)0.0062 (18)
C2010.0626 (19)0.0606 (17)0.057 (2)0.0112 (15)0.0004 (16)0.0115 (16)
C2020.078 (2)0.0596 (19)0.077 (3)0.0132 (16)0.007 (2)0.0219 (18)
C2030.069 (2)0.0457 (17)0.095 (3)0.0081 (16)0.015 (2)0.0045 (18)
C2040.0490 (16)0.0574 (17)0.067 (2)0.0017 (13)0.0032 (14)0.0039 (15)
C2050.0347 (13)0.0511 (14)0.0419 (17)0.0028 (11)0.0076 (11)0.0005 (13)
C2060.0302 (12)0.0524 (15)0.0396 (16)0.0021 (10)0.0037 (11)0.0001 (12)
C2070.0363 (16)0.0539 (14)0.0412 (18)0.0112 (11)0.0025 (13)0.0006 (14)
C2080.0363 (17)0.0478 (18)0.0292 (17)0.0069 (10)0.0042 (15)0.0009 (11)
C2090.0442 (17)0.0560 (17)0.0307 (16)0.0095 (13)0.0025 (14)0.0017 (12)
C2100.0385 (14)0.0583 (17)0.0357 (18)0.0052 (13)0.0012 (12)0.0000 (13)
C2110.0386 (15)0.0543 (16)0.0356 (17)0.0007 (12)0.0044 (13)0.0004 (13)
C2120.0398 (14)0.0554 (15)0.0475 (17)0.0015 (11)0.0014 (12)0.0041 (13)
C2130.0381 (14)0.0539 (16)0.059 (2)0.0064 (12)0.0039 (12)0.0030 (14)
C2140.0522 (19)0.0525 (16)0.0440 (19)0.0039 (13)0.0036 (14)0.0060 (13)
C2150.0524 (18)0.0563 (16)0.068 (2)0.0093 (14)0.0005 (15)0.0010 (16)
C2160.0412 (15)0.0617 (17)0.061 (2)0.0008 (13)0.0061 (14)0.0001 (15)
C2170.0412 (14)0.0563 (15)0.0381 (16)0.0012 (11)0.0046 (12)0.0027 (12)
C2180.081 (2)0.0767 (19)0.047 (2)0.0087 (17)0.0085 (17)0.0109 (16)
C2190.113 (3)0.068 (2)0.055 (3)0.0074 (17)0.014 (2)0.0202 (17)
C2200.0406 (16)0.140 (3)0.047 (2)0.0144 (16)0.0090 (14)0.011 (2)
C2210.088 (2)0.0556 (17)0.072 (2)0.0082 (16)0.0092 (19)0.0044 (16)
C2220.0353 (14)0.0508 (15)0.0356 (17)0.0079 (12)0.0090 (12)0.0023 (13)
O100.0586 (12)0.0677 (12)0.0632 (15)0.0089 (10)0.0251 (11)0.0067 (10)
O110.0702 (13)0.0505 (11)0.102 (2)0.0034 (10)0.0021 (13)0.0043 (11)
O200.0656 (13)0.0721 (12)0.0595 (15)0.0131 (11)0.0297 (12)0.0007 (11)
O210.0692 (13)0.0507 (11)0.0718 (16)0.0028 (9)0.0004 (11)0.0006 (11)
Geometric parameters (Å, º) top
C100—C1011.405 (4)C202—C2031.375 (5)
C100—C1051.381 (4)C203—H2030.9300
C101—H1010.9300C204—H2040.9300
C101—C1021.373 (4)C204—C2031.395 (5)
C102—H1020.9300C205—C2041.386 (4)
C102—C1031.378 (5)C206—H2060.9800
C103—H1030.9300C206—C2171.566 (4)
C104—H1040.9300C206—C2071.529 (4)
C104—C1031.381 (4)C206—C2051.515 (3)
C105—C1041.402 (3)C207—H20B0.9700
C106—H1060.9800C207—H20A0.9700
C106—C1171.573 (4)C208—C2071.521 (4)
C106—C1071.553 (4)C208—C2091.467 (4)
C106—C1051.508 (3)C208—C2101.326 (3)
C107—H10B0.9700C210—H2100.9300
C107—H10A0.9700C210—C2111.450 (4)
C108—C1091.502 (3)C211—C2121.406 (4)
C108—C1071.498 (4)C211—C2161.385 (4)
C108—C1101.357 (3)C212—H2120.9300
C109—C1001.491 (4)C212—C2131.372 (4)
C110—H1100.9300C213—H2130.9300
C110—C1111.476 (4)C214—C2151.383 (4)
C111—C1121.392 (4)C214—C2131.381 (4)
C111—C1161.389 (4)C215—H2150.9300
C112—H1120.9300C216—H2160.9300
C113—H1130.9300C216—C2151.369 (4)
C113—C1141.375 (4)C217—C2201.534 (4)
C113—C1121.366 (4)C217—C2191.526 (4)
C115—H1150.9300C217—C2181.520 (4)
C115—C1161.381 (4)C218—H21C0.9600
C115—C1141.375 (4)C218—H21B0.9600
C116—H1160.9300C218—H21A0.9600
C117—C1181.532 (4)C219—H21F0.9600
C117—C1191.527 (4)C219—H21E0.9600
C117—C1201.525 (4)C219—H21D0.9600
C118—H11F0.9600C220—H22C0.9600
C118—H11E0.9600C220—H22B0.9600
C118—H11D0.9600C220—H22A0.9600
C119—H11C0.9600C221—H22F0.9600
C119—H11B0.9600C221—H22E0.9600
C119—H11A0.9600C221—H22D0.9600
C120—H12C0.9600C222—C2091.462 (4)
C120—H12B0.9600C222—C2051.421 (4)
C120—H12A0.9600C222—C2011.387 (4)
C121—H12F0.9600O10—C1091.226 (3)
C121—H12E0.9600O11—C1211.434 (4)
C121—H12D0.9600O11—C1141.364 (3)
C201—H2010.9300O20—C2091.238 (3)
C201—C2021.361 (4)O21—C2211.430 (3)
C202—H2020.9300O21—C2141.366 (3)
C101—C100—C109118.0 (3)C202—C201—H201119.1
C105—C100—C109121.4 (2)C202—C201—C222121.8 (3)
C105—C100—C101120.7 (2)C203—C202—H202120.3
C100—C101—H101119.7C201—C202—H202120.3
C102—C101—H101119.7C201—C202—C203119.4 (3)
C102—C101—C100120.6 (3)C204—C203—H203119.6
C103—C102—H102120.4C202—C203—H203119.6
C101—C102—H102120.4C202—C203—C204120.8 (3)
C101—C102—C103119.2 (3)C203—C204—H204119.9
C104—C103—H103119.7C205—C204—H204119.9
C102—C103—H103119.7C205—C204—C203120.1 (3)
C102—C103—C104120.5 (3)C222—C205—C206119.6 (2)
C105—C104—H104119.4C204—C205—C206121.7 (3)
C103—C104—H104119.4C204—C205—C222118.6 (2)
C103—C104—C105121.3 (3)C217—C206—H206106.3
C104—C105—C106121.4 (2)C207—C206—H206106.3
C100—C105—C106120.9 (2)C205—C206—H206106.3
C100—C105—C104117.7 (2)C207—C206—C217115.1 (2)
C117—C106—H106105.9C205—C206—C217112.84 (19)
C107—C106—H106105.9C205—C206—C207109.3 (2)
C105—C106—H106105.9H20A—C207—H20B107.6
C107—C106—C117115.1 (2)C206—C207—H20B108.6
C105—C106—C117113.7 (2)C208—C207—H20B108.6
C105—C106—C107109.6 (2)C206—C207—H20A108.6
H10A—C107—H10B107.8C208—C207—H20A108.6
C106—C107—H10B108.9C208—C207—C206114.5 (2)
C108—C107—H10B108.9C209—C208—C207115.9 (2)
C106—C107—H10A108.9C210—C208—C207125.9 (2)
C108—C107—H10A108.9C210—C208—C209118.1 (3)
C108—C107—C106113.2 (2)C222—C209—C208119.4 (3)
C107—C108—C109117.7 (2)O20—C209—C208121.0 (3)
C110—C108—C109115.6 (3)O20—C209—C222119.6 (2)
C110—C108—C107126.8 (2)C211—C210—H210113.6
C100—C109—C108116.9 (2)C208—C210—H210113.6
O10—C109—C108122.2 (2)C208—C210—C211132.7 (3)
O10—C109—C100120.9 (2)C212—C211—C210125.4 (2)
C111—C110—H110115.3C216—C211—C210119.1 (2)
C108—C110—H110115.3C216—C211—C212115.5 (2)
C108—C110—C111129.4 (3)C211—C212—H212119.1
C112—C111—C110125.4 (2)C213—C212—H212119.1
C116—C111—C110117.1 (3)C213—C212—C211121.8 (2)
C116—C111—C112117.4 (3)C214—C213—H213119.8
C111—C112—H112119.7C212—C213—H213119.8
C113—C112—H112119.7C212—C213—C214120.4 (2)
C113—C112—C111120.6 (2)C213—C214—C215119.5 (2)
C114—C113—H113119.4O21—C214—C215124.5 (3)
C112—C113—H113119.4O21—C214—C213116.0 (2)
C112—C113—C114121.2 (3)C214—C215—H215120.5
C113—C114—C115119.6 (3)C216—C215—H215120.5
O11—C114—C115124.4 (3)C216—C215—C214119.0 (2)
O11—C114—C113116.0 (3)C211—C216—H216118.1
C116—C115—H115120.5C215—C216—H216118.1
C114—C115—H115120.5C215—C216—C211123.8 (3)
C114—C115—C116119.0 (2)C220—C217—C206112.8 (2)
C111—C116—H116119.0C219—C217—C206109.8 (2)
C115—C116—H116119.0C218—C217—C206110.3 (2)
C115—C116—C111122.1 (3)C219—C217—C220108.6 (3)
C118—C117—C106109.0 (2)C218—C217—C220107.8 (2)
C119—C117—C106109.6 (2)C218—C217—C219107.5 (3)
C120—C117—C106112.8 (2)H21B—C218—H21C109.5
C119—C117—C118107.4 (3)H21A—C218—H21C109.5
C120—C117—C118108.8 (3)C217—C218—H21C109.5
C120—C117—C119109.1 (3)H21A—C218—H21B109.5
H11E—C118—H11F109.5C217—C218—H21B109.5
H11D—C118—H11F109.5C217—C218—H21A109.5
C117—C118—H11F109.5H21E—C219—H21F109.5
H11D—C118—H11E109.5H21D—C219—H21F109.5
C117—C118—H11E109.5C217—C219—H21F109.5
C117—C118—H11D109.5H21D—C219—H21E109.5
H11B—C119—H11C109.5C217—C219—H21E109.5
H11A—C119—H11C109.5C217—C219—H21D109.5
C117—C119—H11C109.5H22B—C220—H22C109.5
H11A—C119—H11B109.5H22A—C220—H22C109.5
C117—C119—H11B109.5C217—C220—H22C109.5
C117—C119—H11A109.5H22A—C220—H22B109.5
H12B—C120—H12C109.5C217—C220—H22B109.5
H12A—C120—H12C109.5C217—C220—H22A109.5
C117—C120—H12C109.5H22E—C221—H22F109.5
H12A—C120—H12B109.5H22D—C221—H22F109.5
C117—C120—H12B109.5O21—C221—H22F109.5
C117—C120—H12A109.5H22D—C221—H22E109.5
H12E—C121—H12F109.5O21—C221—H22E109.5
H12D—C121—H12F109.5O21—C221—H22D109.5
O11—C121—H12F109.5C205—C222—C209120.9 (2)
H12D—C121—H12E109.5C201—C222—C209120.0 (3)
O11—C121—H12E109.5C201—C222—C205119.0 (3)
O11—C121—H12D109.5C114—O11—C121118.6 (2)
C222—C201—H201119.1C214—O21—C221118.1 (2)
Hydrogen-bond geometry (Å, º) top
Cg3 and Cg7 are the centroids of the C111–C116 and C211–C216 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C104—H104···O21i0.932.533.439 (3)167
C121—H12D···Cg70.962.923.801 (4)153
C221—H22F···Cg30.962.863.686 (4)144
Symmetry code: (i) x+1/2, y+1, z.

Experimental details

Crystal data
Chemical formulaC22H24O2
Mr320.41
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)296
a, b, c (Å)11.2265 (2), 21.7630 (5), 14.8001 (4)
V3)3615.99 (14)
Z8
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.24 × 0.17 × 0.16
Data collection
DiffractometerBruker APEXII CCD detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
20114, 6654, 4552
Rint0.033
(sin θ/λ)max1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.147, 1.03
No. of reflections6654
No. of parameters441
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.41, 0.21

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
Cg3 and Cg7 are the centroids of the C111–C116 and C211–C216 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C104—H104···O21i0.932.533.439 (3)167
C121—H12D···Cg70.962.923.801 (4)153
C221—H22F···Cg30.962.863.686 (4)144
Symmetry code: (i) x+1/2, y+1, z.
 

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

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