organic compounds
2-[(E)-4-Methoxybenzylidene]-1,2,3,4-tetrahydronaphthalen-1-one
aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah, Saudi Arabia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: edward.tiekink@gmail.com
Two independent molecules (A and B) comprise the of the title compound, C18H16O2. Molecule B is virtually superimposable upon A. Minor differences are noted in the dihedral angles between the terminal benzene rings of 56.03 (10) and 54.62 (10)°, and in the orientations of methoxy groups with respect to the benzene rings to which they are attached [C—O—C—C torsion angles = 169.11 (19) and −172.37 (18)°]. The cyclohexene ring of each fused ring system has a screw-boat conformation. In the crystal, C—H⋯π interactions assemble molecules into a supramolecular array in the ab plane.
Related literature
For the activity of related species developed for the treatment of Chagas disease, see: Vera-DiVaio et al. (2009). For the structure of the 2-methoxy derivative, see: Dimmock et al. (2002). For see: Cremer & Pople (1975).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
https://doi.org/10.1107/S160053681202805X/bt5948sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681202805X/bt5948Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S160053681202805X/bt5948Isup3.cml
A solution of the 4-methoxybenzaldehyde (1.3 g, 0.01 M) in ethanol (20 ml) was added to a stirred solution of 1-tetralone (1.46 g,0.01 M) in ethanolic KOH (20 ml, 20%), and stirring was maintained at room temperature for 6 h. The reaction mixture was then poured onto water (200 ml) and set aside overnight. The precipitated solid product was collected by filtration, washed with water, dried and recrystallized from ethanol. Yield: 92%.
H-atoms were placed in calculated positions [C—H = 0.95 Å, Uiso(H) = 1.2Ueq(C)] and were included in the
in the riding model approximation. One reflection, i.e. (-3 6 3), was omitted from the final owing to poor agreement.The
of the title compound, 2-(4-methoxybenzylidene)-3,4-dihydro-2H-naphthalen-1-one (I), was investigated owing to its relationship to some active compounds developed for the treatment of Chagas disease (Vera-DiVaio et al., 2009).Two independent molecules comprise the
of (I), Fig. 1. The inverted structure of the O3-containing molecule is virtually super-imposable upon the O1-containing molecule, Fig. 2. The cyclohexene ring of each fused ring system has a screw boat conformation (Cremer & Pople, 1975). A difference between the molecules is seen in the dihedral angles between the terminal benzene rings of 56.03 (10) and 54.62 (10)°, respectively. The methoxy groups are co-planar with the benzene rings to which they are attached as seen in the C18—O2—C15—C14 and C36—O4—C33—C32 torsion angles of 169.11 (19) and -172.37 (18)°, respectively. The conformation about each ethylene bond is E. The overall observed for the independent molecules of (I) resembles that seen in the 2-methoxy derivative (Dimmock et al., 2002).The presence of C—H···π interactions link molecules into a supramolecular array in the ab plane in the of (I), Fig. 3 and Table 1. Layers stack along the c axis with no specific interactions between them (Fig. 4).
For the activity of related species developed for the treatment of Chagas disease, see: Vera-DiVaio et al. (2009). For the structure of the 2-methoxy derivative, see: Dimmock et al. (2002). For
see: Cremer & Pople (1975).Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. | |
Fig. 2. Superimposition of the two independent molecules in (I). The fused ring systems have been superimposed. The O1 and inverted O3-containing molecules are shown as red and blue images, respectively. | |
Fig. 3. A view of the supramolecular array in the ab plane in (I) mediated by C—H···π interactions shown as purple dashed lines. | |
Fig. 4. A view in projection down the a axis of the unit-cell contents of (I), showing the stacking supramolecular layers along the c axis. The C—H···π interactions shown as purple dashed lines. |
C18H16O2 | F(000) = 1120 |
Mr = 264.31 | Dx = 1.308 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3418 reflections |
a = 6.8289 (4) Å | θ = 2.7–27.5° |
b = 14.7444 (8) Å | µ = 0.08 mm−1 |
c = 26.7258 (14) Å | T = 100 K |
β = 93.757 (5)° | Prism, light-yellow |
V = 2685.2 (3) Å3 | 0.40 × 0.20 × 0.10 mm |
Z = 8 |
Agilent SuperNova Dual diffractometer with an Atlas detector | 6195 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 3813 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.054 |
Detector resolution: 10.4041 pixels mm-1 | θmax = 27.6°, θmin = 2.7° |
ω scan | h = −8→8 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −19→15 |
Tmin = 0.766, Tmax = 1.000 | l = −34→27 |
18691 measured reflections |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.187 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
6195 reflections | (Δ/σ)max < 0.001 |
361 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C18H16O2 | V = 2685.2 (3) Å3 |
Mr = 264.31 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.8289 (4) Å | µ = 0.08 mm−1 |
b = 14.7444 (8) Å | T = 100 K |
c = 26.7258 (14) Å | 0.40 × 0.20 × 0.10 mm |
β = 93.757 (5)° |
Agilent SuperNova Dual diffractometer with an Atlas detector | 6195 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | 3813 reflections with I > 2σ(I) |
Tmin = 0.766, Tmax = 1.000 | Rint = 0.054 |
18691 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.187 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.27 e Å−3 |
6195 reflections | Δρmin = −0.25 e Å−3 |
361 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 | ||
O1 | 0.6701 (2) | 0.77015 (11) | 0.24286 (5) | 0.0275 (4) | |
O2 | −0.2580 (2) | 0.79768 (10) | 0.02451 (5) | 0.0278 (4) | |
O3 | 1.2130 (2) | 0.55355 (11) | 0.26086 (6) | 0.0292 (4) | |
O4 | 0.2783 (2) | 0.52827 (10) | 0.04328 (5) | 0.0268 (4) | |
C1 | 0.5156 (3) | 0.78348 (13) | 0.26276 (8) | 0.0191 (5) | |
C2 | 0.5128 (3) | 0.78434 (13) | 0.31863 (7) | 0.0192 (5) | |
C3 | 0.6731 (3) | 0.74880 (14) | 0.34768 (8) | 0.0255 (5) | |
H3 | 0.7842 | 0.7269 | 0.3318 | 0.031* | |
C4 | 0.6701 (4) | 0.74553 (15) | 0.39950 (8) | 0.0293 (5) | |
H4 | 0.7778 | 0.7204 | 0.4191 | 0.035* | |
C5 | 0.5088 (4) | 0.77917 (15) | 0.42253 (8) | 0.0289 (5) | |
H5 | 0.5069 | 0.7775 | 0.4580 | 0.035* | |
C6 | 0.3502 (3) | 0.81528 (14) | 0.39402 (8) | 0.0246 (5) | |
H6 | 0.2412 | 0.8386 | 0.4103 | 0.029* | |
C7 | 0.3488 (3) | 0.81776 (13) | 0.34180 (8) | 0.0205 (5) | |
C8 | 0.1784 (3) | 0.85520 (14) | 0.30966 (7) | 0.0207 (5) | |
H8A | 0.2059 | 0.9189 | 0.3008 | 0.025* | |
H8B | 0.0590 | 0.8545 | 0.3288 | 0.025* | |
C9 | 0.1421 (3) | 0.79936 (14) | 0.26173 (8) | 0.0203 (5) | |
H9A | 0.1016 | 0.7372 | 0.2705 | 0.024* | |
H9B | 0.0343 | 0.8271 | 0.2404 | 0.024* | |
C10 | 0.3253 (3) | 0.79488 (13) | 0.23293 (8) | 0.0186 (4) | |
C11 | 0.3302 (3) | 0.80015 (13) | 0.18286 (7) | 0.0188 (5) | |
H11 | 0.4575 | 0.8033 | 0.1706 | 0.023* | |
C12 | 0.1669 (3) | 0.80180 (13) | 0.14431 (7) | 0.0191 (5) | |
C13 | 0.1890 (3) | 0.84882 (14) | 0.09931 (7) | 0.0208 (5) | |
H13 | 0.3059 | 0.8822 | 0.0953 | 0.025* | |
C14 | 0.0440 (3) | 0.84745 (14) | 0.06078 (8) | 0.0216 (5) | |
H14 | 0.0606 | 0.8809 | 0.0310 | 0.026* | |
C15 | −0.1261 (3) | 0.79728 (14) | 0.06547 (7) | 0.0209 (5) | |
C16 | −0.1524 (3) | 0.74988 (14) | 0.10958 (7) | 0.0205 (5) | |
H16 | −0.2689 | 0.7159 | 0.1131 | 0.025* | |
C17 | −0.0066 (3) | 0.75278 (13) | 0.14846 (7) | 0.0192 (5) | |
H17 | −0.0254 | 0.7206 | 0.1786 | 0.023* | |
C18 | −0.4166 (3) | 0.73482 (16) | 0.02424 (9) | 0.0307 (5) | |
H18A | −0.5007 | 0.7424 | −0.0066 | 0.046* | |
H18B | −0.4935 | 0.7460 | 0.0533 | 0.046* | |
H18C | −0.3647 | 0.6728 | 0.0258 | 0.046* | |
C19 | 1.0573 (3) | 0.54246 (13) | 0.28040 (8) | 0.0193 (5) | |
C20 | 1.0499 (3) | 0.54485 (13) | 0.33611 (8) | 0.0191 (5) | |
C21 | 1.2083 (3) | 0.58197 (14) | 0.36510 (8) | 0.0245 (5) | |
H21 | 1.3201 | 0.6033 | 0.3493 | 0.029* | |
C22 | 1.2022 (3) | 0.58761 (14) | 0.41678 (8) | 0.0274 (5) | |
H22 | 1.3095 | 0.6130 | 0.4365 | 0.033* | |
C23 | 1.0381 (3) | 0.55593 (14) | 0.43966 (8) | 0.0268 (5) | |
H23 | 1.0329 | 0.5605 | 0.4750 | 0.032* | |
C24 | 0.8820 (3) | 0.51760 (14) | 0.41117 (8) | 0.0234 (5) | |
H24 | 0.7722 | 0.4949 | 0.4273 | 0.028* | |
C25 | 0.8846 (3) | 0.51211 (14) | 0.35905 (8) | 0.0199 (5) | |
C26 | 0.7168 (3) | 0.47224 (14) | 0.32696 (8) | 0.0225 (5) | |
H26A | 0.5962 | 0.4737 | 0.3456 | 0.027* | |
H26B | 0.7462 | 0.4081 | 0.3194 | 0.027* | |
C27 | 0.6822 (3) | 0.52514 (14) | 0.27784 (7) | 0.0201 (5) | |
H27A | 0.5783 | 0.4948 | 0.2564 | 0.024* | |
H27B | 0.6365 | 0.5871 | 0.2852 | 0.024* | |
C28 | 0.8670 (3) | 0.53087 (13) | 0.25012 (7) | 0.0184 (5) | |
C29 | 0.8732 (3) | 0.52698 (13) | 0.19981 (8) | 0.0197 (5) | |
H29 | 1.0006 | 0.5245 | 0.1876 | 0.024* | |
C30 | 0.7102 (3) | 0.52606 (13) | 0.16160 (7) | 0.0185 (4) | |
C31 | 0.7301 (3) | 0.47902 (14) | 0.11619 (8) | 0.0214 (5) | |
H31 | 0.8470 | 0.4458 | 0.1118 | 0.026* | |
C32 | 0.5845 (3) | 0.48000 (14) | 0.07810 (8) | 0.0221 (5) | |
H32 | 0.6005 | 0.4471 | 0.0481 | 0.027* | |
C33 | 0.4132 (3) | 0.52956 (14) | 0.08374 (8) | 0.0214 (5) | |
C34 | 0.3894 (3) | 0.57657 (14) | 0.12784 (7) | 0.0207 (5) | |
H34 | 0.2727 | 0.6102 | 0.1317 | 0.025* | |
C35 | 0.5359 (3) | 0.57460 (14) | 0.16638 (7) | 0.0203 (5) | |
H35 | 0.5176 | 0.6067 | 0.1965 | 0.024* | |
C36 | 0.1135 (3) | 0.58699 (15) | 0.04526 (8) | 0.0268 (5) | |
H36A | 0.0275 | 0.5796 | 0.0147 | 0.040* | |
H36B | 0.1586 | 0.6500 | 0.0479 | 0.040* | |
H36C | 0.0408 | 0.5718 | 0.0746 | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0184 (8) | 0.0352 (9) | 0.0293 (9) | 0.0018 (7) | 0.0038 (7) | −0.0026 (7) |
O2 | 0.0298 (9) | 0.0303 (9) | 0.0224 (8) | −0.0040 (7) | −0.0051 (7) | 0.0049 (6) |
O3 | 0.0190 (8) | 0.0375 (10) | 0.0316 (9) | −0.0025 (7) | 0.0057 (7) | −0.0020 (7) |
O4 | 0.0313 (9) | 0.0285 (9) | 0.0200 (8) | 0.0075 (7) | −0.0034 (7) | −0.0018 (6) |
C1 | 0.0190 (11) | 0.0134 (10) | 0.0248 (11) | 0.0002 (8) | 0.0009 (9) | −0.0007 (8) |
C2 | 0.0211 (11) | 0.0151 (10) | 0.0209 (11) | −0.0019 (8) | −0.0016 (9) | 0.0001 (8) |
C3 | 0.0256 (12) | 0.0184 (11) | 0.0320 (13) | −0.0009 (9) | −0.0017 (10) | −0.0032 (9) |
C4 | 0.0392 (14) | 0.0192 (12) | 0.0275 (12) | −0.0014 (10) | −0.0125 (11) | 0.0008 (9) |
C5 | 0.0428 (15) | 0.0212 (12) | 0.0222 (12) | −0.0095 (10) | −0.0032 (11) | 0.0017 (9) |
C6 | 0.0301 (13) | 0.0182 (11) | 0.0258 (12) | −0.0049 (9) | 0.0057 (10) | −0.0001 (9) |
C7 | 0.0228 (12) | 0.0161 (11) | 0.0227 (11) | −0.0065 (8) | 0.0022 (9) | −0.0016 (8) |
C8 | 0.0188 (11) | 0.0207 (11) | 0.0230 (11) | 0.0024 (8) | 0.0034 (9) | −0.0009 (8) |
C9 | 0.0163 (11) | 0.0214 (11) | 0.0231 (11) | 0.0001 (8) | 0.0007 (9) | −0.0002 (8) |
C10 | 0.0163 (11) | 0.0155 (10) | 0.0240 (11) | 0.0015 (8) | 0.0019 (9) | −0.0009 (8) |
C11 | 0.0163 (11) | 0.0173 (11) | 0.0231 (11) | 0.0010 (8) | 0.0031 (9) | −0.0018 (8) |
C12 | 0.0186 (11) | 0.0162 (11) | 0.0227 (11) | 0.0024 (8) | 0.0035 (9) | −0.0023 (8) |
C13 | 0.0229 (12) | 0.0174 (11) | 0.0226 (11) | −0.0006 (9) | 0.0044 (9) | −0.0019 (8) |
C14 | 0.0273 (12) | 0.0191 (11) | 0.0185 (11) | 0.0019 (9) | 0.0028 (9) | 0.0023 (8) |
C15 | 0.0239 (12) | 0.0201 (11) | 0.0186 (11) | 0.0036 (9) | 0.0006 (9) | −0.0010 (8) |
C16 | 0.0204 (11) | 0.0176 (11) | 0.0237 (12) | −0.0002 (8) | 0.0024 (9) | −0.0017 (8) |
C17 | 0.0229 (11) | 0.0176 (11) | 0.0175 (11) | 0.0028 (8) | 0.0039 (9) | 0.0003 (8) |
C18 | 0.0262 (13) | 0.0367 (14) | 0.0280 (13) | −0.0040 (10) | −0.0058 (10) | 0.0001 (10) |
C19 | 0.0167 (11) | 0.0141 (10) | 0.0270 (12) | −0.0012 (8) | 0.0019 (9) | −0.0009 (8) |
C20 | 0.0211 (11) | 0.0144 (10) | 0.0218 (11) | 0.0017 (8) | 0.0013 (9) | 0.0021 (8) |
C21 | 0.0209 (12) | 0.0193 (12) | 0.0328 (13) | −0.0026 (9) | −0.0023 (10) | 0.0012 (9) |
C22 | 0.0332 (13) | 0.0192 (12) | 0.0288 (13) | −0.0052 (10) | −0.0054 (10) | 0.0012 (9) |
C23 | 0.0388 (14) | 0.0186 (12) | 0.0226 (12) | −0.0022 (10) | −0.0003 (10) | −0.0003 (9) |
C24 | 0.0284 (12) | 0.0177 (11) | 0.0244 (12) | −0.0012 (9) | 0.0043 (10) | 0.0001 (8) |
C25 | 0.0211 (11) | 0.0158 (10) | 0.0228 (11) | 0.0032 (8) | 0.0011 (9) | 0.0009 (8) |
C26 | 0.0208 (11) | 0.0224 (12) | 0.0246 (11) | −0.0017 (9) | 0.0039 (9) | 0.0003 (9) |
C27 | 0.0186 (11) | 0.0202 (11) | 0.0217 (11) | −0.0009 (9) | 0.0028 (9) | 0.0003 (8) |
C28 | 0.0171 (11) | 0.0148 (10) | 0.0233 (11) | −0.0012 (8) | 0.0023 (9) | 0.0009 (8) |
C29 | 0.0201 (11) | 0.0148 (11) | 0.0246 (11) | −0.0008 (8) | 0.0047 (9) | 0.0007 (8) |
C30 | 0.0209 (11) | 0.0161 (10) | 0.0190 (11) | −0.0016 (8) | 0.0048 (9) | 0.0028 (8) |
C31 | 0.0233 (12) | 0.0190 (11) | 0.0226 (11) | 0.0045 (9) | 0.0070 (9) | 0.0035 (8) |
C32 | 0.0299 (12) | 0.0197 (11) | 0.0169 (11) | 0.0030 (9) | 0.0040 (9) | −0.0010 (8) |
C33 | 0.0261 (12) | 0.0190 (11) | 0.0191 (11) | −0.0007 (9) | 0.0002 (9) | 0.0035 (8) |
C34 | 0.0219 (11) | 0.0181 (11) | 0.0226 (11) | 0.0041 (9) | 0.0049 (9) | 0.0017 (8) |
C35 | 0.0255 (12) | 0.0177 (11) | 0.0183 (11) | 0.0009 (9) | 0.0044 (9) | 0.0009 (8) |
C36 | 0.0251 (12) | 0.0270 (12) | 0.0279 (12) | 0.0031 (10) | −0.0026 (10) | 0.0032 (9) |
O1—C1 | 1.229 (2) | C18—H18A | 0.9800 |
O2—C15 | 1.371 (2) | C18—H18B | 0.9800 |
O2—C18 | 1.426 (3) | C18—H18C | 0.9800 |
O3—C19 | 1.226 (2) | C19—C20 | 1.494 (3) |
O4—C33 | 1.374 (2) | C19—C28 | 1.495 (3) |
O4—C36 | 1.424 (2) | C20—C21 | 1.400 (3) |
C1—C10 | 1.489 (3) | C20—C25 | 1.405 (3) |
C1—C2 | 1.494 (3) | C21—C22 | 1.387 (3) |
C2—C3 | 1.401 (3) | C21—H21 | 0.9500 |
C2—C7 | 1.404 (3) | C22—C23 | 1.392 (3) |
C3—C4 | 1.387 (3) | C22—H22 | 0.9500 |
C3—H3 | 0.9500 | C23—C24 | 1.389 (3) |
C4—C5 | 1.388 (3) | C23—H23 | 0.9500 |
C4—H4 | 0.9500 | C24—C25 | 1.396 (3) |
C5—C6 | 1.389 (3) | C24—H24 | 0.9500 |
C5—H5 | 0.9500 | C25—C26 | 1.505 (3) |
C6—C7 | 1.395 (3) | C26—C27 | 1.532 (3) |
C6—H6 | 0.9500 | C26—H26A | 0.9900 |
C7—C8 | 1.506 (3) | C26—H26B | 0.9900 |
C8—C9 | 1.529 (3) | C27—C28 | 1.507 (3) |
C8—H8A | 0.9900 | C27—H27A | 0.9900 |
C8—H8B | 0.9900 | C27—H27B | 0.9900 |
C9—C10 | 1.512 (3) | C28—C29 | 1.349 (3) |
C9—H9A | 0.9900 | C29—C30 | 1.460 (3) |
C9—H9B | 0.9900 | C29—H29 | 0.9500 |
C10—C11 | 1.343 (3) | C30—C35 | 1.402 (3) |
C11—C12 | 1.468 (3) | C30—C31 | 1.412 (3) |
C11—H11 | 0.9500 | C31—C32 | 1.375 (3) |
C12—C17 | 1.398 (3) | C31—H31 | 0.9500 |
C12—C13 | 1.405 (3) | C32—C33 | 1.396 (3) |
C13—C14 | 1.381 (3) | C32—H32 | 0.9500 |
C13—H13 | 0.9500 | C33—C34 | 1.386 (3) |
C14—C15 | 1.389 (3) | C34—C35 | 1.388 (3) |
C14—H14 | 0.9500 | C34—H34 | 0.9500 |
C15—C16 | 1.392 (3) | C35—H35 | 0.9500 |
C16—C17 | 1.392 (3) | C36—H36A | 0.9800 |
C16—H16 | 0.9500 | C36—H36B | 0.9800 |
C17—H17 | 0.9500 | C36—H36C | 0.9800 |
C15—O2—C18 | 117.43 (16) | H18B—C18—H18C | 109.5 |
C33—O4—C36 | 116.96 (16) | O3—C19—C20 | 120.56 (19) |
O1—C1—C10 | 122.05 (18) | O3—C19—C28 | 122.16 (19) |
O1—C1—C2 | 120.08 (19) | C20—C19—C28 | 117.21 (17) |
C10—C1—C2 | 117.80 (17) | C21—C20—C25 | 120.44 (19) |
C3—C2—C7 | 120.22 (19) | C21—C20—C19 | 119.04 (18) |
C3—C2—C1 | 119.34 (18) | C25—C20—C19 | 120.51 (18) |
C7—C2—C1 | 120.41 (18) | C22—C21—C20 | 120.1 (2) |
C4—C3—C2 | 120.3 (2) | C22—C21—H21 | 119.9 |
C4—C3—H3 | 119.9 | C20—C21—H21 | 119.9 |
C2—C3—H3 | 119.9 | C21—C22—C23 | 119.7 (2) |
C5—C4—C3 | 119.6 (2) | C21—C22—H22 | 120.2 |
C5—C4—H4 | 120.2 | C23—C22—H22 | 120.2 |
C3—C4—H4 | 120.2 | C24—C23—C22 | 120.5 (2) |
C4—C5—C6 | 120.5 (2) | C24—C23—H23 | 119.8 |
C4—C5—H5 | 119.8 | C22—C23—H23 | 119.8 |
C6—C5—H5 | 119.8 | C23—C24—C25 | 120.7 (2) |
C5—C6—C7 | 120.8 (2) | C23—C24—H24 | 119.6 |
C5—C6—H6 | 119.6 | C25—C24—H24 | 119.6 |
C7—C6—H6 | 119.6 | C24—C25—C20 | 118.59 (19) |
C6—C7—C2 | 118.61 (19) | C24—C25—C26 | 122.15 (18) |
C6—C7—C8 | 122.30 (18) | C20—C25—C26 | 119.27 (18) |
C2—C7—C8 | 119.09 (18) | C25—C26—C27 | 111.00 (17) |
C7—C8—C9 | 110.93 (17) | C25—C26—H26A | 109.4 |
C7—C8—H8A | 109.5 | C27—C26—H26A | 109.4 |
C9—C8—H8A | 109.5 | C25—C26—H26B | 109.4 |
C7—C8—H8B | 109.5 | C27—C26—H26B | 109.4 |
C9—C8—H8B | 109.5 | H26A—C26—H26B | 108.0 |
H8A—C8—H8B | 108.0 | C28—C27—C26 | 111.27 (17) |
C10—C9—C8 | 110.85 (17) | C28—C27—H27A | 109.4 |
C10—C9—H9A | 109.5 | C26—C27—H27A | 109.4 |
C8—C9—H9A | 109.5 | C28—C27—H27B | 109.4 |
C10—C9—H9B | 109.5 | C26—C27—H27B | 109.4 |
C8—C9—H9B | 109.5 | H27A—C27—H27B | 108.0 |
H9A—C9—H9B | 108.1 | C29—C28—C19 | 117.47 (18) |
C11—C10—C1 | 117.53 (18) | C29—C28—C27 | 124.72 (19) |
C11—C10—C9 | 125.45 (19) | C19—C28—C27 | 117.81 (17) |
C1—C10—C9 | 117.02 (17) | C28—C29—C30 | 128.69 (19) |
C10—C11—C12 | 129.27 (19) | C28—C29—H29 | 115.7 |
C10—C11—H11 | 115.4 | C30—C29—H29 | 115.7 |
C12—C11—H11 | 115.4 | C35—C30—C31 | 117.31 (19) |
C17—C12—C13 | 117.51 (19) | C35—C30—C29 | 122.98 (18) |
C17—C12—C11 | 122.97 (18) | C31—C30—C29 | 119.60 (18) |
C13—C12—C11 | 119.34 (18) | C32—C31—C30 | 121.70 (19) |
C14—C13—C12 | 121.27 (19) | C32—C31—H31 | 119.1 |
C14—C13—H13 | 119.4 | C30—C31—H31 | 119.1 |
C12—C13—H13 | 119.4 | C31—C32—C33 | 119.71 (19) |
C13—C14—C15 | 120.21 (19) | C31—C32—H32 | 120.1 |
C13—C14—H14 | 119.9 | C33—C32—H32 | 120.1 |
C15—C14—H14 | 119.9 | O4—C33—C34 | 124.49 (19) |
O2—C15—C14 | 115.78 (18) | O4—C33—C32 | 115.54 (18) |
O2—C15—C16 | 124.29 (19) | C34—C33—C32 | 120.0 (2) |
C14—C15—C16 | 119.9 (2) | C33—C34—C35 | 120.11 (19) |
C15—C16—C17 | 119.39 (19) | C33—C34—H34 | 119.9 |
C15—C16—H16 | 120.3 | C35—C34—H34 | 119.9 |
C17—C16—H16 | 120.3 | C34—C35—C30 | 121.19 (19) |
C16—C17—C12 | 121.67 (19) | C34—C35—H35 | 119.4 |
C16—C17—H17 | 119.2 | C30—C35—H35 | 119.4 |
C12—C17—H17 | 119.2 | O4—C36—H36A | 109.5 |
O2—C18—H18A | 109.5 | O4—C36—H36B | 109.5 |
O2—C18—H18B | 109.5 | H36A—C36—H36B | 109.5 |
H18A—C18—H18B | 109.5 | O4—C36—H36C | 109.5 |
O2—C18—H18C | 109.5 | H36A—C36—H36C | 109.5 |
H18A—C18—H18C | 109.5 | H36B—C36—H36C | 109.5 |
O1—C1—C2—C3 | −15.4 (3) | O3—C19—C20—C21 | 16.0 (3) |
C10—C1—C2—C3 | 161.88 (18) | C28—C19—C20—C21 | −160.95 (18) |
O1—C1—C2—C7 | 166.67 (19) | O3—C19—C20—C25 | −165.3 (2) |
C10—C1—C2—C7 | −16.1 (3) | C28—C19—C20—C25 | 17.7 (3) |
C7—C2—C3—C4 | 0.6 (3) | C25—C20—C21—C22 | −0.7 (3) |
C1—C2—C3—C4 | −177.35 (18) | C19—C20—C21—C22 | 177.95 (19) |
C2—C3—C4—C5 | −1.1 (3) | C20—C21—C22—C23 | 0.2 (3) |
C3—C4—C5—C6 | 0.6 (3) | C21—C22—C23—C24 | 0.9 (3) |
C4—C5—C6—C7 | 0.6 (3) | C22—C23—C24—C25 | −1.5 (3) |
C5—C6—C7—C2 | −1.1 (3) | C23—C24—C25—C20 | 1.0 (3) |
C5—C6—C7—C8 | 179.15 (19) | C23—C24—C25—C26 | −179.12 (19) |
C3—C2—C7—C6 | 0.5 (3) | C21—C20—C25—C24 | 0.1 (3) |
C1—C2—C7—C6 | 178.42 (18) | C19—C20—C25—C24 | −178.53 (18) |
C3—C2—C7—C8 | −179.74 (18) | C21—C20—C25—C26 | −179.76 (18) |
C1—C2—C7—C8 | −1.8 (3) | C19—C20—C25—C26 | 1.6 (3) |
C6—C7—C8—C9 | −142.08 (19) | C24—C25—C26—C27 | 142.0 (2) |
C2—C7—C8—C9 | 38.1 (2) | C20—C25—C26—C27 | −38.1 (3) |
C7—C8—C9—C10 | −56.1 (2) | C25—C26—C27—C28 | 54.7 (2) |
O1—C1—C10—C11 | −7.2 (3) | O3—C19—C28—C29 | 4.3 (3) |
C2—C1—C10—C11 | 175.64 (17) | C20—C19—C28—C29 | −178.81 (17) |
O1—C1—C10—C9 | 172.68 (19) | O3—C19—C28—C27 | −175.23 (19) |
C2—C1—C10—C9 | −4.5 (3) | C20—C19—C28—C27 | 1.7 (3) |
C8—C9—C10—C11 | −140.1 (2) | C26—C27—C28—C29 | 143.1 (2) |
C8—C9—C10—C1 | 40.1 (2) | C26—C27—C28—C19 | −37.4 (2) |
C1—C10—C11—C12 | 172.93 (19) | C19—C28—C29—C30 | −172.60 (19) |
C9—C10—C11—C12 | −6.9 (3) | C27—C28—C29—C30 | 6.9 (3) |
C10—C11—C12—C17 | −35.3 (3) | C28—C29—C30—C35 | 35.2 (3) |
C10—C11—C12—C13 | 149.7 (2) | C28—C29—C30—C31 | −148.7 (2) |
C17—C12—C13—C14 | 0.6 (3) | C35—C30—C31—C32 | −0.4 (3) |
C11—C12—C13—C14 | 175.92 (18) | C29—C30—C31—C32 | −176.69 (18) |
C12—C13—C14—C15 | −1.5 (3) | C30—C31—C32—C33 | 0.9 (3) |
C18—O2—C15—C14 | 169.11 (19) | C36—O4—C33—C34 | 6.9 (3) |
C18—O2—C15—C16 | −10.1 (3) | C36—O4—C33—C32 | −172.37 (18) |
C13—C14—C15—O2 | −177.76 (18) | C31—C32—C33—O4 | 178.49 (17) |
C13—C14—C15—C16 | 1.5 (3) | C31—C32—C33—C34 | −0.8 (3) |
O2—C15—C16—C17 | 178.62 (18) | O4—C33—C34—C35 | −179.09 (18) |
C14—C15—C16—C17 | −0.5 (3) | C32—C33—C34—C35 | 0.1 (3) |
C15—C16—C17—C12 | −0.4 (3) | C33—C34—C35—C30 | 0.5 (3) |
C13—C12—C17—C16 | 0.3 (3) | C31—C30—C35—C34 | −0.3 (3) |
C11—C12—C17—C16 | −174.79 (18) | C29—C30—C35—C34 | 175.87 (18) |
Cg1–Cg3 are the centroids of the C20–C25, C2–C7 and C12–C17 benzene rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···Cg1i | 0.95 | 2.70 | 3.486 (2) | 140 |
C21—H21···Cg2ii | 0.95 | 2.97 | 3.595 (2) | 124 |
C31—H31···Cg2iii | 0.95 | 2.64 | 3.411 (2) | 139 |
C36—H36B···Cg3 | 0.98 | 2.88 | 3.592 (2) | 131 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) x+1, y, z; (iii) −x+3/2, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C18H16O2 |
Mr | 264.31 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 6.8289 (4), 14.7444 (8), 26.7258 (14) |
β (°) | 93.757 (5) |
V (Å3) | 2685.2 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.40 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Agilent SuperNova Dual diffractometer with an Atlas detector |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2012) |
Tmin, Tmax | 0.766, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18691, 6195, 3813 |
Rint | 0.054 |
(sin θ/λ)max (Å−1) | 0.651 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.187, 0.99 |
No. of reflections | 6195 |
No. of parameters | 361 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.25 |
Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).
Cg1–Cg3 are the centroids of the C20–C25, C2–C7 and C12–C17 benzene rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···Cg1i | 0.95 | 2.70 | 3.486 (2) | 140 |
C21—H21···Cg2ii | 0.95 | 2.97 | 3.595 (2) | 124 |
C31—H31···Cg2iii | 0.95 | 2.64 | 3.411 (2) | 139 |
C36—H36B···Cg3 | 0.98 | 2.88 | 3.592 (2) | 131 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) x+1, y, z; (iii) −x+3/2, y−1/2, −z+1/2. |
Footnotes
‡Additional correspondence author, e-mail: aasiri2@kau.edu.sa.
Acknowledgements
The authors are grateful to King Abdulaziz University for providing research facilities. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).
References
Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The crystal structure of the title compound, 2-(4-methoxybenzylidene)-3,4-dihydro-2H-naphthalen-1-one (I), was investigated owing to its relationship to some active compounds developed for the treatment of Chagas disease (Vera-DiVaio et al., 2009).
Two independent molecules comprise the asymmetric unit of (I), Fig. 1. The inverted structure of the O3-containing molecule is virtually super-imposable upon the O1-containing molecule, Fig. 2. The cyclohexene ring of each fused ring system has a screw boat conformation (Cremer & Pople, 1975). A difference between the molecules is seen in the dihedral angles between the terminal benzene rings of 56.03 (10) and 54.62 (10)°, respectively. The methoxy groups are co-planar with the benzene rings to which they are attached as seen in the C18—O2—C15—C14 and C36—O4—C33—C32 torsion angles of 169.11 (19) and -172.37 (18)°, respectively. The conformation about each ethylene bond is E. The overall molecular conformation observed for the independent molecules of (I) resembles that seen in the 2-methoxy derivative (Dimmock et al., 2002).
The presence of C—H···π interactions link molecules into a supramolecular array in the ab plane in the crystal structure of (I), Fig. 3 and Table 1. Layers stack along the c axis with no specific interactions between them (Fig. 4).