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

Akhazzane, M.; Zouihri, H.; Daoudi, M.; Kerbal, A.; Al Houari, G.

doi:10.1107/S1600536811021969

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1828

doi:10.1107/S1600536811021969

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

Mohamed Akhazzane,^a ^* Hafid Zouihri,^b Maria Daoudi,^a Abdelali Kerbal ^a and Ghali Al Houari ^a

^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 ); 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

Crystal data

C₂₂H₂₄O₂
M_r = 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)
R_int = 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
Δρ_max = 0.41 e Å⁻³
Δρ_min = −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	D⋯A	D—H⋯A
C104—H104⋯O21ⁱ	0.93	2.53	3.439 (3)	167
C121—H12D⋯Cg7	0.96	2.92	3.801 (4)	153
C221—H22F⋯Cg3	0.96	2.86	3.686 (4)	144
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+1, z]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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 ).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536811021969/dn2694sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811021969/dn2694Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811021969/dn2694Isup3.cml

checkCIF report

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.

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

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

C₂₂H₂₄O₂	F(000) = 1376
M_r = 320.41	D_x = 1.177 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 256 reflections
a = 11.2265 (2) Å	θ = 2.4–25.8°
b = 21.7630 (5) Å	µ = 0.07 mm⁻¹
c = 14.8001 (4) Å	T = 296 K
V = 3615.99 (14) Å³	Prism, colourless
Z = 8	0.24 × 0.17 × 0.16 mm

Data collection top

Bruker APEXII CCD detector diffractometer	4552 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.033
Graphite monochromator	θ_max = 26.5°, θ_min = 0.9°
ω and ϕ scans	h = −13→14
20114 measured reflections	k = −24→27
6654 independent reflections	l = −16→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.088P)²] where P = (F_o² + 2F_c²)/3
6654 reflections	(Δ/σ)_max = 0.011
441 parameters	Δρ_max = 0.41 e Å⁻³
1 restraint	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₂H₂₄O₂	V = 3615.99 (14) Å³
M_r = 320.41	Z = 8
Orthorhombic, Pca2₁	Mo Kα radiation
a = 11.2265 (2) Å	µ = 0.07 mm⁻¹
b = 21.7630 (5) Å	T = 296 K
c = 14.8001 (4) Å	0.24 × 0.17 × 0.16 mm

Data collection top

Bruker APEXII CCD detector diffractometer	4552 reflections with I > 2σ(I)
20114 measured reflections	R_int = 0.033
6654 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	1 restraint
wR(F²) = 0.147	H-atom parameters constrained
S = 1.03	Δρ_max = 0.41 e Å⁻³
6654 reflections	Δρ_min = −0.21 e Å⁻³
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

	x	y	z	U_iso*/U_eq
C100	0.6470 (2)	0.38382 (11)	0.4388 (2)	0.0411 (6)
C101	0.6110 (2)	0.33059 (12)	0.4851 (2)	0.0532 (7)
C102	0.6531 (3)	0.27392 (13)	0.4598 (3)	0.0622 (8)
C103	0.7326 (3)	0.26978 (13)	0.3892 (3)	0.0641 (9)
C104	0.7685 (2)	0.32188 (12)	0.3434 (2)	0.0552 (7)
C105	0.7248 (2)	0.38008 (11)	0.36673 (19)	0.0424 (6)
C106	0.7596 (2)	0.43672 (10)	0.31438 (19)	0.0415 (6)
C107	0.7704 (3)	0.49220 (11)	0.3798 (2)	0.0429 (7)
C108	0.6628 (2)	0.50071 (10)	0.4383 (2)	0.0403 (7)
C109	0.5989 (2)	0.44403 (12)	0.4701 (2)	0.0440 (7)
C110	0.6144 (2)	0.55490 (11)	0.4650 (2)	0.0444 (7)
C111	0.6550 (2)	0.61823 (12)	0.4470 (2)	0.0439 (7)
C112	0.7729 (2)	0.63626 (11)	0.4354 (2)	0.0534 (8)
C113	0.8008 (2)	0.69646 (12)	0.4200 (2)	0.0605 (8)
C114	0.7139 (3)	0.74091 (12)	0.4167 (2)	0.0531 (8)
C115	0.5966 (3)	0.72479 (12)	0.4296 (2)	0.0577 (8)
C116	0.5687 (3)	0.66397 (12)	0.4458 (2)	0.0583 (8)
C117	0.6807 (2)	0.44838 (12)	0.22824 (19)	0.0475 (7)
C118	0.6908 (3)	0.39284 (16)	0.1651 (2)	0.0806 (10)
C119	0.7281 (4)	0.50413 (15)	0.1770 (3)	0.0739 (12)
C120	0.5498 (2)	0.45874 (18)	0.2510 (3)	0.0786 (11)
C121	0.6667 (3)	0.84831 (13)	0.4022 (3)	0.0801 (11)
C201	0.6361 (3)	1.16663 (12)	0.0896 (2)	0.0603 (8)
C202	0.5944 (3)	1.22365 (14)	0.1102 (3)	0.0714 (10)
C203	0.5132 (3)	1.23039 (13)	0.1791 (3)	0.0699 (11)
C204	0.4739 (2)	1.17962 (12)	0.2283 (2)	0.0579 (8)
C205	0.5184 (2)	1.12162 (11)	0.20951 (19)	0.0426 (6)
C206	0.4829 (2)	1.06589 (11)	0.26467 (19)	0.0407 (6)
C207	0.4753 (3)	1.00980 (13)	0.2027 (2)	0.0438 (7)
C208	0.5855 (2)	0.99897 (10)	0.1451 (2)	0.0378 (7)
C209	0.6456 (2)	1.05429 (12)	0.1115 (2)	0.0437 (7)
C210	0.6308 (2)	0.94469 (11)	0.1232 (2)	0.0442 (7)
C211	0.5944 (2)	0.88216 (12)	0.1428 (2)	0.0428 (7)
C212	0.4772 (2)	0.86312 (12)	0.1611 (2)	0.0476 (7)
C213	0.4502 (2)	0.80294 (11)	0.1798 (2)	0.0504 (7)
C214	0.5383 (3)	0.75867 (12)	0.1790 (2)	0.0496 (8)
C215	0.6544 (2)	0.77552 (12)	0.1599 (2)	0.0589 (8)
C216	0.6790 (2)	0.83588 (12)	0.1417 (2)	0.0547 (7)
C217	0.5618 (2)	1.05718 (11)	0.3510 (2)	0.0452 (6)
C218	0.5489 (3)	1.11228 (14)	0.4134 (2)	0.0682 (9)
C219	0.5204 (5)	1.00059 (14)	0.4031 (3)	0.0789 (13)
C220	0.6944 (2)	1.04974 (16)	0.3289 (2)	0.0761 (11)
C221	0.5906 (3)	0.65256 (12)	0.1973 (3)	0.0718 (9)
C222	0.5994 (2)	1.11478 (12)	0.1365 (2)	0.0406 (7)
H101	0.5583	0.3338	0.5333	0.064*
H102	0.6281	0.2387	0.4900	0.075*
H103	0.7624	0.2316	0.3722	0.077*
H104	0.8228	0.3183	0.2962	0.066*
H106	0.8403	0.4290	0.2919	0.050*
H10A	0.8396	0.4863	0.4181	0.052*
H10B	0.7831	0.5293	0.3448	0.052*
H110	0.5456	0.5517	0.4998	0.053*
H112	0.8333	0.6071	0.4381	0.064*
H113	0.8800	0.7076	0.4116	0.073*
H115	0.5370	0.7544	0.4274	0.069*
H116	0.4897	0.6533	0.4563	0.070*
H11A	0.8092	0.4968	0.1594	0.111*
H11B	0.7245	0.5397	0.2152	0.111*
H11C	0.6804	0.5109	0.1241	0.111*
H11D	0.6521	0.4019	0.1088	0.121*
H11E	0.6532	0.3579	0.1926	0.121*
H11F	0.7733	0.3838	0.1543	0.121*
H12A	0.5066	0.4679	0.1967	0.118*
H12B	0.5428	0.4925	0.2924	0.118*
H12C	0.5177	0.4223	0.2783	0.118*
H12D	0.6148	0.8442	0.3510	0.120*
H12E	0.7072	0.8871	0.3992	0.120*
H12F	0.6207	0.8463	0.4568	0.120*
H201	0.6908	1.1623	0.0428	0.072*
H202	0.6205	1.2578	0.0779	0.086*
H203	0.4843	1.2693	0.1931	0.084*
H204	0.4176	1.1847	0.2739	0.070*
H206	0.4018	1.0737	0.2862	0.049*
H20A	0.4615	0.9736	0.2395	0.053*
H20B	0.4071	1.0147	0.1631	0.053*
H210	0.6996	0.9472	0.0884	0.053*
H212	0.4163	0.8921	0.1606	0.057*
H213	0.3721	0.7919	0.1931	0.060*
H215	0.7148	0.7463	0.1595	0.071*
H216	0.7572	0.8464	0.1277	0.066*
H21A	0.5970	1.1062	0.4662	0.102*
H21B	0.4669	1.1167	0.4309	0.102*
H21C	0.5744	1.1487	0.3824	0.102*
H21D	0.5608	0.9988	0.4602	0.118*
H21E	0.5382	0.9643	0.3688	0.118*
H21F	0.4360	1.0031	0.4131	0.118*
H22A	0.7213	1.0847	0.2950	0.114*
H22B	0.7059	1.0131	0.2937	0.114*
H22C	0.7391	1.0467	0.3840	0.114*
H22D	0.6287	0.6507	0.1394	0.108*
H22E	0.5534	0.6138	0.2101	0.108*
H22F	0.6489	0.6614	0.2430	0.108*
O10	0.51340 (18)	0.44643 (8)	0.52145 (17)	0.0632 (6)
O11	0.7524 (2)	0.79948 (8)	0.40158 (18)	0.0742 (7)
O20	0.73570 (19)	1.05053 (8)	0.06354 (16)	0.0657 (6)
O21	0.50231 (18)	0.69992 (8)	0.19669 (16)	0.0639 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C100	0.0373 (14)	0.0491 (15)	0.0369 (16)	−0.0045 (12)	−0.0024 (13)	0.0011 (13)
C101	0.0571 (17)	0.0589 (17)	0.0436 (18)	−0.0105 (13)	0.0010 (14)	0.0046 (14)
C102	0.074 (2)	0.0477 (16)	0.065 (2)	−0.0026 (14)	0.0001 (17)	0.0072 (15)
C103	0.070 (2)	0.0445 (15)	0.078 (3)	0.0091 (16)	−0.0053 (19)	−0.0052 (16)
C104	0.0481 (16)	0.0600 (16)	0.058 (2)	0.0076 (13)	−0.0010 (14)	−0.0029 (15)
C105	0.0349 (14)	0.0490 (13)	0.0433 (17)	0.0012 (11)	−0.0073 (12)	−0.0024 (12)
C106	0.0301 (12)	0.0516 (14)	0.0429 (16)	0.0020 (11)	0.0038 (11)	−0.0047 (12)
C107	0.0359 (15)	0.0509 (14)	0.0420 (19)	−0.0005 (11)	0.0009 (13)	−0.0037 (13)
C108	0.0369 (17)	0.0494 (18)	0.0347 (18)	−0.0027 (10)	0.0020 (16)	−0.0018 (10)
C109	0.0373 (16)	0.0582 (17)	0.0366 (18)	−0.0070 (12)	0.0006 (14)	−0.0034 (13)
C110	0.0425 (16)	0.0555 (17)	0.0353 (18)	0.0003 (12)	0.0009 (13)	−0.0046 (13)
C111	0.0478 (17)	0.0484 (15)	0.0356 (17)	0.0019 (13)	0.0002 (14)	−0.0067 (13)
C112	0.0429 (16)	0.0490 (15)	0.068 (2)	0.0053 (12)	−0.0141 (14)	−0.0067 (14)
C113	0.0430 (16)	0.0589 (17)	0.079 (2)	−0.0047 (13)	−0.0091 (15)	−0.0010 (16)
C114	0.057 (2)	0.0472 (15)	0.056 (2)	0.0006 (13)	−0.0072 (15)	0.0006 (14)
C115	0.0543 (18)	0.0510 (16)	0.068 (2)	0.0108 (13)	0.0060 (15)	0.0006 (15)
C116	0.0471 (17)	0.0599 (17)	0.068 (2)	0.0043 (13)	0.0112 (15)	0.0004 (16)
C117	0.0410 (14)	0.0669 (16)	0.0345 (15)	0.0031 (12)	0.0009 (11)	−0.0042 (13)
C118	0.100 (3)	0.094 (2)	0.049 (2)	0.008 (2)	−0.0109 (19)	−0.0183 (19)
C119	0.070 (3)	0.097 (3)	0.055 (3)	0.0033 (16)	−0.002 (2)	0.0214 (18)
C120	0.0443 (17)	0.143 (3)	0.049 (2)	0.0093 (18)	−0.0089 (15)	0.005 (2)
C121	0.089 (2)	0.0523 (17)	0.099 (3)	0.0078 (16)	−0.002 (2)	0.0062 (18)
C201	0.0626 (19)	0.0606 (17)	0.057 (2)	−0.0112 (15)	0.0004 (16)	0.0115 (16)
C202	0.078 (2)	0.0596 (19)	0.077 (3)	−0.0132 (16)	−0.007 (2)	0.0219 (18)
C203	0.069 (2)	0.0457 (17)	0.095 (3)	0.0081 (16)	−0.015 (2)	0.0045 (18)
C204	0.0490 (16)	0.0574 (17)	0.067 (2)	0.0017 (13)	−0.0032 (14)	−0.0039 (15)
C205	0.0347 (13)	0.0511 (14)	0.0419 (17)	−0.0028 (11)	−0.0076 (11)	0.0005 (13)
C206	0.0302 (12)	0.0524 (15)	0.0396 (16)	−0.0021 (10)	0.0037 (11)	−0.0001 (12)
C207	0.0363 (16)	0.0539 (14)	0.0412 (18)	−0.0112 (11)	0.0025 (13)	−0.0006 (14)
C208	0.0363 (17)	0.0478 (18)	0.0292 (17)	−0.0069 (10)	−0.0042 (15)	−0.0009 (11)
C209	0.0442 (17)	0.0560 (17)	0.0307 (16)	−0.0095 (13)	−0.0025 (14)	−0.0017 (12)
C210	0.0385 (14)	0.0583 (17)	0.0357 (18)	−0.0052 (13)	0.0012 (12)	0.0000 (13)
C211	0.0386 (15)	0.0543 (16)	0.0356 (17)	−0.0007 (12)	−0.0044 (13)	−0.0004 (13)
C212	0.0398 (14)	0.0554 (15)	0.0475 (17)	0.0015 (11)	−0.0014 (12)	−0.0041 (13)
C213	0.0381 (14)	0.0539 (16)	0.059 (2)	−0.0064 (12)	0.0039 (12)	−0.0030 (14)
C214	0.0522 (19)	0.0525 (16)	0.0440 (19)	−0.0039 (13)	−0.0036 (14)	−0.0060 (13)
C215	0.0524 (18)	0.0563 (16)	0.068 (2)	0.0093 (14)	−0.0005 (15)	−0.0010 (16)
C216	0.0412 (15)	0.0617 (17)	0.061 (2)	0.0008 (13)	0.0061 (14)	0.0001 (15)
C217	0.0412 (14)	0.0563 (15)	0.0381 (16)	0.0012 (11)	0.0046 (12)	−0.0027 (12)
C218	0.081 (2)	0.0767 (19)	0.047 (2)	0.0087 (17)	−0.0085 (17)	−0.0109 (16)
C219	0.113 (3)	0.068 (2)	0.055 (3)	−0.0074 (17)	−0.014 (2)	0.0202 (17)
C220	0.0406 (16)	0.140 (3)	0.047 (2)	0.0144 (16)	−0.0090 (14)	−0.011 (2)
C221	0.088 (2)	0.0556 (17)	0.072 (2)	0.0082 (16)	−0.0092 (19)	0.0044 (16)
C222	0.0353 (14)	0.0508 (15)	0.0356 (17)	−0.0079 (12)	−0.0090 (12)	0.0023 (13)
O10	0.0586 (12)	0.0677 (12)	0.0632 (15)	−0.0089 (10)	0.0251 (11)	−0.0067 (10)
O11	0.0702 (13)	0.0505 (11)	0.102 (2)	−0.0034 (10)	0.0021 (13)	0.0043 (11)
O20	0.0656 (13)	0.0721 (12)	0.0595 (15)	−0.0131 (11)	0.0297 (12)	−0.0007 (11)
O21	0.0692 (13)	0.0507 (11)	0.0718 (16)	−0.0028 (9)	−0.0004 (11)	0.0006 (11)

Geometric parameters (Å, º) top

C100—C101	1.405 (4)	C202—C203	1.375 (5)
C100—C105	1.381 (4)	C203—H203	0.9300
C101—H101	0.9300	C204—H204	0.9300
C101—C102	1.373 (4)	C204—C203	1.395 (5)
C102—H102	0.9300	C205—C204	1.386 (4)
C102—C103	1.378 (5)	C206—H206	0.9800
C103—H103	0.9300	C206—C217	1.566 (4)
C104—H104	0.9300	C206—C207	1.529 (4)
C104—C103	1.381 (4)	C206—C205	1.515 (3)
C105—C104	1.402 (3)	C207—H20B	0.9700
C106—H106	0.9800	C207—H20A	0.9700
C106—C117	1.573 (4)	C208—C207	1.521 (4)
C106—C107	1.553 (4)	C208—C209	1.467 (4)
C106—C105	1.508 (3)	C208—C210	1.326 (3)
C107—H10B	0.9700	C210—H210	0.9300
C107—H10A	0.9700	C210—C211	1.450 (4)
C108—C109	1.502 (3)	C211—C212	1.406 (4)
C108—C107	1.498 (4)	C211—C216	1.385 (4)
C108—C110	1.357 (3)	C212—H212	0.9300
C109—C100	1.491 (4)	C212—C213	1.372 (4)
C110—H110	0.9300	C213—H213	0.9300
C110—C111	1.476 (4)	C214—C215	1.383 (4)
C111—C112	1.392 (4)	C214—C213	1.381 (4)
C111—C116	1.389 (4)	C215—H215	0.9300
C112—H112	0.9300	C216—H216	0.9300
C113—H113	0.9300	C216—C215	1.369 (4)
C113—C114	1.375 (4)	C217—C220	1.534 (4)
C113—C112	1.366 (4)	C217—C219	1.526 (4)
C115—H115	0.9300	C217—C218	1.520 (4)
C115—C116	1.381 (4)	C218—H21C	0.9600
C115—C114	1.375 (4)	C218—H21B	0.9600
C116—H116	0.9300	C218—H21A	0.9600
C117—C118	1.532 (4)	C219—H21F	0.9600
C117—C119	1.527 (4)	C219—H21E	0.9600
C117—C120	1.525 (4)	C219—H21D	0.9600
C118—H11F	0.9600	C220—H22C	0.9600
C118—H11E	0.9600	C220—H22B	0.9600
C118—H11D	0.9600	C220—H22A	0.9600
C119—H11C	0.9600	C221—H22F	0.9600
C119—H11B	0.9600	C221—H22E	0.9600
C119—H11A	0.9600	C221—H22D	0.9600
C120—H12C	0.9600	C222—C209	1.462 (4)
C120—H12B	0.9600	C222—C205	1.421 (4)
C120—H12A	0.9600	C222—C201	1.387 (4)
C121—H12F	0.9600	O10—C109	1.226 (3)
C121—H12E	0.9600	O11—C121	1.434 (4)
C121—H12D	0.9600	O11—C114	1.364 (3)
C201—H201	0.9300	O20—C209	1.238 (3)
C201—C202	1.361 (4)	O21—C221	1.430 (3)
C202—H202	0.9300	O21—C214	1.366 (3)

C101—C100—C109	118.0 (3)	C202—C201—H201	119.1
C105—C100—C109	121.4 (2)	C202—C201—C222	121.8 (3)
C105—C100—C101	120.7 (2)	C203—C202—H202	120.3
C100—C101—H101	119.7	C201—C202—H202	120.3
C102—C101—H101	119.7	C201—C202—C203	119.4 (3)
C102—C101—C100	120.6 (3)	C204—C203—H203	119.6
C103—C102—H102	120.4	C202—C203—H203	119.6
C101—C102—H102	120.4	C202—C203—C204	120.8 (3)
C101—C102—C103	119.2 (3)	C203—C204—H204	119.9
C104—C103—H103	119.7	C205—C204—H204	119.9
C102—C103—H103	119.7	C205—C204—C203	120.1 (3)
C102—C103—C104	120.5 (3)	C222—C205—C206	119.6 (2)
C105—C104—H104	119.4	C204—C205—C206	121.7 (3)
C103—C104—H104	119.4	C204—C205—C222	118.6 (2)
C103—C104—C105	121.3 (3)	C217—C206—H206	106.3
C104—C105—C106	121.4 (2)	C207—C206—H206	106.3
C100—C105—C106	120.9 (2)	C205—C206—H206	106.3
C100—C105—C104	117.7 (2)	C207—C206—C217	115.1 (2)
C117—C106—H106	105.9	C205—C206—C217	112.84 (19)
C107—C106—H106	105.9	C205—C206—C207	109.3 (2)
C105—C106—H106	105.9	H20A—C207—H20B	107.6
C107—C106—C117	115.1 (2)	C206—C207—H20B	108.6
C105—C106—C117	113.7 (2)	C208—C207—H20B	108.6
C105—C106—C107	109.6 (2)	C206—C207—H20A	108.6
H10A—C107—H10B	107.8	C208—C207—H20A	108.6
C106—C107—H10B	108.9	C208—C207—C206	114.5 (2)
C108—C107—H10B	108.9	C209—C208—C207	115.9 (2)
C106—C107—H10A	108.9	C210—C208—C207	125.9 (2)
C108—C107—H10A	108.9	C210—C208—C209	118.1 (3)
C108—C107—C106	113.2 (2)	C222—C209—C208	119.4 (3)
C107—C108—C109	117.7 (2)	O20—C209—C208	121.0 (3)
C110—C108—C109	115.6 (3)	O20—C209—C222	119.6 (2)
C110—C108—C107	126.8 (2)	C211—C210—H210	113.6
C100—C109—C108	116.9 (2)	C208—C210—H210	113.6
O10—C109—C108	122.2 (2)	C208—C210—C211	132.7 (3)
O10—C109—C100	120.9 (2)	C212—C211—C210	125.4 (2)
C111—C110—H110	115.3	C216—C211—C210	119.1 (2)
C108—C110—H110	115.3	C216—C211—C212	115.5 (2)
C108—C110—C111	129.4 (3)	C211—C212—H212	119.1
C112—C111—C110	125.4 (2)	C213—C212—H212	119.1
C116—C111—C110	117.1 (3)	C213—C212—C211	121.8 (2)
C116—C111—C112	117.4 (3)	C214—C213—H213	119.8
C111—C112—H112	119.7	C212—C213—H213	119.8
C113—C112—H112	119.7	C212—C213—C214	120.4 (2)
C113—C112—C111	120.6 (2)	C213—C214—C215	119.5 (2)
C114—C113—H113	119.4	O21—C214—C215	124.5 (3)
C112—C113—H113	119.4	O21—C214—C213	116.0 (2)
C112—C113—C114	121.2 (3)	C214—C215—H215	120.5
C113—C114—C115	119.6 (3)	C216—C215—H215	120.5
O11—C114—C115	124.4 (3)	C216—C215—C214	119.0 (2)
O11—C114—C113	116.0 (3)	C211—C216—H216	118.1
C116—C115—H115	120.5	C215—C216—H216	118.1
C114—C115—H115	120.5	C215—C216—C211	123.8 (3)
C114—C115—C116	119.0 (2)	C220—C217—C206	112.8 (2)
C111—C116—H116	119.0	C219—C217—C206	109.8 (2)
C115—C116—H116	119.0	C218—C217—C206	110.3 (2)
C115—C116—C111	122.1 (3)	C219—C217—C220	108.6 (3)
C118—C117—C106	109.0 (2)	C218—C217—C220	107.8 (2)
C119—C117—C106	109.6 (2)	C218—C217—C219	107.5 (3)
C120—C117—C106	112.8 (2)	H21B—C218—H21C	109.5
C119—C117—C118	107.4 (3)	H21A—C218—H21C	109.5
C120—C117—C118	108.8 (3)	C217—C218—H21C	109.5
C120—C117—C119	109.1 (3)	H21A—C218—H21B	109.5
H11E—C118—H11F	109.5	C217—C218—H21B	109.5
H11D—C118—H11F	109.5	C217—C218—H21A	109.5
C117—C118—H11F	109.5	H21E—C219—H21F	109.5
H11D—C118—H11E	109.5	H21D—C219—H21F	109.5
C117—C118—H11E	109.5	C217—C219—H21F	109.5
C117—C118—H11D	109.5	H21D—C219—H21E	109.5
H11B—C119—H11C	109.5	C217—C219—H21E	109.5
H11A—C119—H11C	109.5	C217—C219—H21D	109.5
C117—C119—H11C	109.5	H22B—C220—H22C	109.5
H11A—C119—H11B	109.5	H22A—C220—H22C	109.5
C117—C119—H11B	109.5	C217—C220—H22C	109.5
C117—C119—H11A	109.5	H22A—C220—H22B	109.5
H12B—C120—H12C	109.5	C217—C220—H22B	109.5
H12A—C120—H12C	109.5	C217—C220—H22A	109.5
C117—C120—H12C	109.5	H22E—C221—H22F	109.5
H12A—C120—H12B	109.5	H22D—C221—H22F	109.5
C117—C120—H12B	109.5	O21—C221—H22F	109.5
C117—C120—H12A	109.5	H22D—C221—H22E	109.5
H12E—C121—H12F	109.5	O21—C221—H22E	109.5
H12D—C121—H12F	109.5	O21—C221—H22D	109.5
O11—C121—H12F	109.5	C205—C222—C209	120.9 (2)
H12D—C121—H12E	109.5	C201—C222—C209	120.0 (3)
O11—C121—H12E	109.5	C201—C222—C205	119.0 (3)
O11—C121—H12D	109.5	C114—O11—C121	118.6 (2)
C222—C201—H201	119.1	C214—O21—C221	118.1 (2)

Hydrogen-bond geometry (Å, º) top

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

D—H···A	D—H	H···A	D···A	D—H···A
C104—H104···O21ⁱ	0.93	2.53	3.439 (3)	167
C121—H12D···Cg7	0.96	2.92	3.801 (4)	153
C221—H22F···Cg3	0.96	2.86	3.686 (4)	144

Symmetry code: (i) x+1/2, −y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₄O₂
M_r	320.41
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	296
a, b, c (Å)	11.2265 (2), 21.7630 (5), 14.8001 (4)
V (Å³)	3615.99 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.24 × 0.17 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	20114, 6654, 4552
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.147, 1.03
No. of reflections	6654
No. of parameters	441
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
C104—H104···O21ⁱ	0.93	2.53	3.439 (3)	167
C121—H12D···Cg7	0.96	2.92	3.801 (4)	153
C221—H22F···Cg3	0.96	2.86	3.686 (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

Akhazzane, M., Zouihri, H., Daran, J.-C., Kerbal, A. & Al Houari, G. (2010). Acta Cryst. E66, o3067. Web of Science CSD CrossRef IUCr Journals Google Scholar
Al Houari, G., Kerbal, A., Bennani, B., Baba, M. F., Daoudi, M. & Ben Hadda, T. (2008). ARKIVOC, xii, 42–50, Google Scholar
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. CrossRef Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358; CrossRef CAS Google Scholar
Kerbal, A., Tshiamala, K., Vebrel, J. & Laude, B. (1988). Bull. Soc. Chim. Belg. 97, 149–161. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 7| July 2011| Page o1828

doi:10.1107/S1600536811021969

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

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organic compounds

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