organic compounds
(8-Benzoyl-2,7-diethoxynaphthalen-1-yl)(phenyl)methanone
aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, 2-24-16 Naka-machi, Koganei, Tokyo 184-8588, Japan
*Correspondence e-mail: aokamoto@cc.tuat.ac.jp
In the title compound, C28H24O4, the benzoyl groups at the 1- and 8-positions of the naphthalene ring system are aligned almost antiparallel, and the benzene rings make a dihedral angle of 20.03 (7)°. The dihedral angles between the benzene rings and the naphthalene ring system are 68.42 (5) and 71.69 (5)°. In the crystal, adjacent molecules are linked via C—H⋯O hydrogen bonds, forming chains propagating along [100].
Related literature
For electrophilic aroylation of naphthalene derivatives, see: Okamoto & Yonezawa (2009); Okamoto et al. (2011). For the structures of closely related compounds, see: Nakaema et al. (2008); Nishijima et al. (2010); Sasagawa et al. (2011); Tsumuki et al. (2011); Muto et al. (2012).
Experimental
Crystal data
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Refinement
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Data collection: PROCESS-AUTO (Rigaku, 1998); cell PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: IL MILIONE (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.
Supporting information
https://doi.org/10.1107/S1600536812049963/su2538sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049963/su2538Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812049963/su2538Isup3.cml
To a 100 ml flask, benzoyl chloride (422 mg, 3.0 mmol), titanium chloride (1.71 g, 9.0 mmol) and methylene chloride (1.5 ml) were stirred at 298 K under nitrogen atmosphere. To reaction mixture thus obtained, 2,7-diethoxynaphtharene (216 mg, 1.0 mmol) and methylene chloride (1.0 ml) were added. After the reaction mixture was stirred at r.t. for 24 h, it was poured into ice-cold water (20 ml). The aqueous layer was extracted with CHCl3 (10 ml × 3). The combined extracts were washed with 2 M aqueous NaOH followed by washing with brine. The organic layers thus obtained were dried over anhydrous MgSO4. The solvent was removed under reduced pressure to give cake. The crude product was purified by recrystallization from CHCl3/methanol (1: 2 v/v) solution (81% yield). Colorless platelet single crystals suitable for X-ray diffraction were obtained by repeated crystallization from a CHCl3/ methanol (1:2 v/v) solution (52% yield). Anal. Calcd for C28H24O4: C 79.22, H5.70. Found: C 79.32, H 5.84.; M.p. = 467–468 K. Spectroscopic data for the title compound are available in the archived CIF.
All the H atoms were located in a difference Fourier map and were subsequently refined as riding atoms: C—H = 0.95 (aromatic), 0.98 (methyl) and 0.99 (methylene) Å, with Uiso(H) = 1.2 Ueq(C).
In the course of our study on selective electrophilic aromatic aroylation of naphthalene ring core, 1,8-diaroylnaphthalene compounds have proved to be formed regioselectively by the aid of a suitable acidic mediator (Okamoto & Yonezawa, 2009, Okamoto et al., 2011). Recently, we have reported the X-ray π···π interactions between benzene rings. As a part of our ongoing studies on the molecular structures of these kinds of homologous molecules, the X-ray of the title compound, is reported on herein.
of 1,8-diaroyled 2,7-dimethoxynaphthalene derivatives such as 1,8-bis(4-aminobenzoyl)-2,7-dimethoxynaphthalene (Nishijima et al., 2010), [8-(4-butoxybenzoyl)-2,7-dimethoxynaphthalen-1-yl](4-butoxyphenyl)methanone [1,8-bis(4-butoxybenzoyl)-2,7-dimethoxynaphthalene] (Sasagawa et al., 2011), [2,7-dimethoxy-8-(2-naphthoyl)naphthalene-1-yl](naphthalene-2-yl)methanone [2,7-dimethoxy-1,8-bis(2-naphthoyl)naphthalene] (Tsumuki et al., 2011), and (3,5-dimethylphenyl)[8-(3,5-dimethylbenzoyl)-2,7-dimethoxynaphthalen-1-yl]methanone (Muto et al., 2012). The simplest molecule in these analogues, 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema et al., 2008), lies across a crystallographic 2-fold axis and the molecular packing is stabilized by C—H···O interactions between carbonyl groups and benzene ring andThe molecule structure of the title molecule is illustrated in Fig. 1. The two benzoyl groups are situated in an (anti)-orientation and twisted away from the attached naphthalene ring. The dihedral angle between the planes of the two benzene rings (C12-C17 & C19-C24) is 20.03 (7)°. The dihedral angles between these benzene rings and the naphthalene (C1-C10) ring are 68.42 (5)° and 71.69 (5)°. These dihedral angles are similar to that reported for 1,8-dibenzoyl-2,7-dimethoxynaphthalene [80.25 (6)°; Nakaema et al., 2008]. The torsion angles between the carbonyl groups and the naphthalene ring are -63.28 (14)° [C9—C1—C11—O3] and -66.19 (14)° [C9—C8—C18—O4]. The C═O groups lie almost in the plane of the attached benzene ring with torsion angles equal to 1.58 (17)° [O3—C11—C12—C17] and 1.44 (17)° [O4—C18—C19—C24].
In the crystal, the molecular packing of the title compound is mainly stabilized by two types of C—H···O interactions involving adjacent molecules and leading to the formation of chains along the a axis (Table 1 and Fig. 2).
For electrophilic aroylation of naphthalene derivatives, see: Okamoto & Yonezawa (2009); Okamoto et al. (2011). For the structures of closely related compounds, see: Nakaema et al. (2008); Nishijima et al. (2010); Sasagawa et al. (2011); Tsumuki et al. (2011); Muto et al. (2012).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell
PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: IL MILIONE (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C28H24O4 | F(000) = 896 |
Mr = 424.47 | Dx = 1.260 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54187 Å |
Hall symbol: -P 2yn | Cell parameters from 37233 reflections |
a = 7.92185 (14) Å | θ = 3.2–68.3° |
b = 20.6794 (4) Å | µ = 0.67 mm−1 |
c = 14.2130 (3) Å | T = 193 K |
β = 106.043 (1)° | Needle, colourless |
V = 2237.68 (7) Å3 | 0.60 × 0.50 × 0.10 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 4076 independent reflections |
Radiation source: fine-focus sealed tube | 3736 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
Detector resolution: 10.000 pixels mm-1 | θmax = 68.2°, θmin = 3.9° |
ω scans | h = −9→9 |
Absorption correction: numerical (NUMABS; Higashi, 1999) | k = −24→24 |
Tmin = 0.689, Tmax = 0.936 | l = −17→17 |
39782 measured reflections |
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)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.091 | w = 1/[σ2(Fo2) + (0.0439P)2 + 0.5163P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
4076 reflections | Δρmax = 0.23 e Å−3 |
292 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0075 (3) |
C28H24O4 | V = 2237.68 (7) Å3 |
Mr = 424.47 | Z = 4 |
Monoclinic, P21/n | Cu Kα radiation |
a = 7.92185 (14) Å | µ = 0.67 mm−1 |
b = 20.6794 (4) Å | T = 193 K |
c = 14.2130 (3) Å | 0.60 × 0.50 × 0.10 mm |
β = 106.043 (1)° |
Rigaku R-AXIS RAPID diffractometer | 4076 independent reflections |
Absorption correction: numerical (NUMABS; Higashi, 1999) | 3736 reflections with I > 2σ(I) |
Tmin = 0.689, Tmax = 0.936 | Rint = 0.041 |
39782 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.23 e Å−3 |
4076 reflections | Δρmin = −0.16 e Å−3 |
292 parameters |
Experimental. Spectroscopic data for the title compound: 1H NMR δ (300 MHz, CDCl3); 0.91 (6H, t, J = 6.9 Hz), 3.95 (4H, q, J = 6.9 Hz), 7.16 (2H, d, J = 9.0 Hz), 7.35 (4H, t, J = 7.2 Hz), 7.49(2H, t, J = 7.2 Hz), 7.73 (4H, d, J = 7.2 Hz), 7.91 (2H, d, J = 9.0 Hz) p.p.m.; 13C NMR δ (75 MHz, CDCl3); 13.92, 64.42, 111.89, 121.27, 125.05, 127.43, 128.54, 129.80, 131.79, 131.95, 138.93, 155.52, 197.04 p.p.m.; IR (KBr, cm-1): 1665 (C═ O), 1612, 1510, 1452 (Ar), 1266 (═C—O—C). |
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 | 0.29349 (11) | 0.08669 (4) | 1.04839 (6) | 0.0381 (2) | |
O2 | −0.21634 (12) | 0.01858 (4) | 0.55669 (6) | 0.0458 (2) | |
O3 | −0.02728 (10) | 0.16304 (4) | 0.86895 (6) | 0.0383 (2) | |
O4 | 0.08625 (10) | 0.12983 (4) | 0.66958 (6) | 0.0414 (2) | |
C1 | 0.12835 (13) | 0.06508 (5) | 0.88895 (8) | 0.0299 (2) | |
C2 | 0.21642 (14) | 0.04134 (5) | 0.98017 (8) | 0.0325 (3) | |
C3 | 0.21668 (15) | −0.02515 (6) | 1.00229 (9) | 0.0367 (3) | |
H3 | 0.2781 | −0.0406 | 1.0654 | 0.044* | |
C4 | 0.12768 (15) | −0.06697 (6) | 0.93199 (9) | 0.0375 (3) | |
H4 | 0.1268 | −0.1117 | 0.9471 | 0.045* | |
C5 | −0.05370 (16) | −0.08988 (6) | 0.76527 (10) | 0.0398 (3) | |
H5 | −0.0536 | −0.1344 | 0.7817 | 0.048* | |
C6 | −0.14091 (16) | −0.07056 (6) | 0.67303 (9) | 0.0410 (3) | |
H6 | −0.2012 | −0.1012 | 0.6258 | 0.049* | |
C7 | −0.14038 (15) | −0.00448 (6) | 0.64861 (9) | 0.0361 (3) | |
C8 | −0.05794 (14) | 0.04132 (5) | 0.71690 (8) | 0.0314 (2) | |
C9 | 0.03474 (13) | 0.02192 (5) | 0.81381 (8) | 0.0302 (2) | |
C10 | 0.03651 (14) | −0.04555 (5) | 0.83711 (9) | 0.0341 (3) | |
C11 | 0.11515 (14) | 0.13756 (5) | 0.87770 (8) | 0.0299 (2) | |
C12 | 0.27340 (14) | 0.17695 (5) | 0.87977 (8) | 0.0320 (2) | |
C13 | 0.43562 (15) | 0.14857 (6) | 0.88777 (9) | 0.0390 (3) | |
H13 | 0.4468 | 0.1028 | 0.8910 | 0.047* | |
C14 | 0.58108 (16) | 0.18650 (7) | 0.89110 (10) | 0.0477 (3) | |
H14 | 0.6918 | 0.1668 | 0.8966 | 0.057* | |
C15 | 0.56497 (18) | 0.25260 (7) | 0.88645 (11) | 0.0542 (4) | |
H15 | 0.6650 | 0.2787 | 0.8893 | 0.065* | |
C16 | 0.4039 (2) | 0.28145 (7) | 0.87758 (13) | 0.0586 (4) | |
H16 | 0.3933 | 0.3272 | 0.8739 | 0.070* | |
C17 | 0.25816 (17) | 0.24361 (6) | 0.87402 (11) | 0.0455 (3) | |
H17 | 0.1474 | 0.2634 | 0.8676 | 0.055* | |
C18 | −0.05219 (14) | 0.10942 (5) | 0.67903 (8) | 0.0310 (2) | |
C19 | −0.21431 (14) | 0.14952 (5) | 0.65338 (8) | 0.0310 (2) | |
C20 | −0.37066 (15) | 0.12789 (6) | 0.66818 (9) | 0.0390 (3) | |
H20 | −0.3762 | 0.0860 | 0.6947 | 0.047* | |
C21 | −0.51890 (16) | 0.16678 (7) | 0.64465 (10) | 0.0459 (3) | |
H21 | −0.6257 | 0.1516 | 0.6547 | 0.055* | |
C22 | −0.51078 (18) | 0.22760 (7) | 0.60655 (10) | 0.0483 (3) | |
H22 | −0.6126 | 0.2541 | 0.5898 | 0.058* | |
C23 | −0.35529 (19) | 0.25015 (7) | 0.59266 (11) | 0.0531 (4) | |
H23 | −0.3498 | 0.2924 | 0.5673 | 0.064* | |
C24 | −0.20769 (17) | 0.21117 (6) | 0.61576 (10) | 0.0435 (3) | |
H24 | −0.1010 | 0.2267 | 0.6058 | 0.052* | |
C25 | 0.42914 (16) | 0.06661 (6) | 1.13328 (9) | 0.0420 (3) | |
H25A | 0.5139 | 0.0379 | 1.1140 | 0.050* | |
H25B | 0.3777 | 0.0429 | 1.1792 | 0.050* | |
C26 | 0.5191 (2) | 0.12683 (7) | 1.18056 (11) | 0.0571 (4) | |
H26A | 0.4357 | 0.1534 | 1.2032 | 0.068* | |
H26B | 0.5624 | 0.1513 | 1.1329 | 0.068* | |
H26C | 0.6181 | 0.1151 | 1.2365 | 0.068* | |
C27 | −0.26626 (18) | −0.02602 (7) | 0.47696 (9) | 0.0469 (3) | |
H27A | −0.3661 | −0.0530 | 0.4830 | 0.056* | |
H27B | −0.1667 | −0.0549 | 0.4766 | 0.056* | |
C28 | −0.31808 (19) | 0.01303 (7) | 0.38490 (10) | 0.0515 (3) | |
H28A | −0.2205 | 0.0413 | 0.3817 | 0.062* | |
H28B | −0.4211 | 0.0394 | 0.3844 | 0.062* | |
H28C | −0.3465 | −0.0160 | 0.3282 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0391 (4) | 0.0380 (4) | 0.0334 (4) | 0.0027 (3) | 0.0035 (3) | 0.0007 (3) |
O2 | 0.0568 (6) | 0.0368 (5) | 0.0362 (5) | 0.0032 (4) | −0.0001 (4) | −0.0053 (4) |
O3 | 0.0266 (4) | 0.0375 (4) | 0.0499 (5) | 0.0040 (3) | 0.0094 (4) | −0.0037 (4) |
O4 | 0.0306 (4) | 0.0456 (5) | 0.0502 (5) | −0.0024 (3) | 0.0149 (4) | 0.0054 (4) |
C1 | 0.0243 (5) | 0.0317 (6) | 0.0356 (6) | 0.0007 (4) | 0.0114 (4) | 0.0011 (4) |
C2 | 0.0275 (5) | 0.0355 (6) | 0.0355 (6) | 0.0016 (4) | 0.0105 (5) | −0.0005 (5) |
C3 | 0.0343 (6) | 0.0389 (6) | 0.0372 (6) | 0.0056 (5) | 0.0103 (5) | 0.0077 (5) |
C4 | 0.0375 (6) | 0.0304 (6) | 0.0463 (7) | 0.0036 (5) | 0.0146 (5) | 0.0069 (5) |
C5 | 0.0424 (7) | 0.0278 (6) | 0.0502 (7) | 0.0005 (5) | 0.0146 (6) | −0.0009 (5) |
C6 | 0.0421 (7) | 0.0326 (6) | 0.0463 (7) | −0.0014 (5) | 0.0090 (6) | −0.0082 (5) |
C7 | 0.0335 (6) | 0.0362 (6) | 0.0376 (6) | 0.0029 (5) | 0.0081 (5) | −0.0026 (5) |
C8 | 0.0271 (5) | 0.0310 (6) | 0.0371 (6) | 0.0027 (4) | 0.0104 (5) | −0.0006 (5) |
C9 | 0.0252 (5) | 0.0309 (5) | 0.0366 (6) | 0.0017 (4) | 0.0120 (4) | 0.0006 (4) |
C10 | 0.0314 (6) | 0.0305 (6) | 0.0423 (7) | 0.0022 (4) | 0.0136 (5) | 0.0014 (5) |
C11 | 0.0263 (5) | 0.0336 (6) | 0.0288 (5) | 0.0019 (4) | 0.0059 (4) | −0.0014 (4) |
C12 | 0.0286 (6) | 0.0341 (6) | 0.0316 (6) | −0.0007 (4) | 0.0054 (4) | 0.0023 (4) |
C13 | 0.0304 (6) | 0.0393 (6) | 0.0472 (7) | 0.0021 (5) | 0.0104 (5) | 0.0066 (5) |
C14 | 0.0273 (6) | 0.0594 (8) | 0.0551 (8) | −0.0003 (5) | 0.0090 (6) | 0.0139 (7) |
C15 | 0.0394 (7) | 0.0570 (9) | 0.0628 (9) | −0.0168 (6) | 0.0085 (6) | 0.0119 (7) |
C16 | 0.0539 (8) | 0.0367 (7) | 0.0840 (11) | −0.0087 (6) | 0.0171 (8) | 0.0089 (7) |
C17 | 0.0377 (7) | 0.0362 (7) | 0.0616 (8) | 0.0017 (5) | 0.0119 (6) | 0.0057 (6) |
C18 | 0.0291 (5) | 0.0345 (6) | 0.0291 (6) | −0.0020 (4) | 0.0077 (4) | −0.0019 (4) |
C19 | 0.0307 (6) | 0.0317 (6) | 0.0295 (6) | −0.0002 (4) | 0.0065 (4) | −0.0018 (4) |
C20 | 0.0327 (6) | 0.0339 (6) | 0.0501 (7) | −0.0020 (5) | 0.0110 (5) | −0.0004 (5) |
C21 | 0.0296 (6) | 0.0488 (7) | 0.0579 (8) | 0.0000 (5) | 0.0097 (6) | −0.0075 (6) |
C22 | 0.0419 (7) | 0.0497 (8) | 0.0476 (8) | 0.0163 (6) | 0.0030 (6) | −0.0005 (6) |
C23 | 0.0581 (8) | 0.0433 (7) | 0.0585 (9) | 0.0130 (6) | 0.0173 (7) | 0.0170 (6) |
C24 | 0.0419 (7) | 0.0410 (7) | 0.0498 (8) | 0.0018 (5) | 0.0162 (6) | 0.0098 (6) |
C25 | 0.0373 (6) | 0.0481 (7) | 0.0360 (6) | 0.0040 (5) | 0.0026 (5) | 0.0033 (5) |
C26 | 0.0538 (8) | 0.0551 (9) | 0.0504 (8) | −0.0017 (7) | −0.0055 (7) | −0.0013 (7) |
C27 | 0.0516 (8) | 0.0469 (7) | 0.0394 (7) | −0.0044 (6) | 0.0082 (6) | −0.0101 (6) |
C28 | 0.0513 (8) | 0.0602 (9) | 0.0406 (7) | −0.0046 (6) | 0.0091 (6) | −0.0049 (6) |
O1—C2 | 1.3657 (14) | C15—C16 | 1.382 (2) |
O1—C25 | 1.4374 (14) | C15—H15 | 0.9500 |
O2—C7 | 1.3645 (15) | C16—C17 | 1.3841 (18) |
O2—C27 | 1.4297 (15) | C16—H16 | 0.9500 |
O3—C11 | 1.2201 (13) | C17—H17 | 0.9500 |
O4—C18 | 1.2167 (13) | C18—C19 | 1.4870 (15) |
C1—C2 | 1.3815 (16) | C19—C20 | 1.3865 (16) |
C1—C9 | 1.4315 (15) | C19—C24 | 1.3890 (17) |
C1—C11 | 1.5079 (15) | C20—C21 | 1.3858 (17) |
C2—C3 | 1.4104 (16) | C20—H20 | 0.9500 |
C3—C4 | 1.3616 (17) | C21—C22 | 1.378 (2) |
C3—H3 | 0.9500 | C21—H21 | 0.9500 |
C4—C10 | 1.4135 (17) | C22—C23 | 1.381 (2) |
C4—H4 | 0.9500 | C22—H22 | 0.9500 |
C5—C6 | 1.3620 (18) | C23—C24 | 1.3830 (18) |
C5—C10 | 1.4108 (17) | C23—H23 | 0.9500 |
C5—H5 | 0.9500 | C24—H24 | 0.9500 |
C6—C7 | 1.4101 (17) | C25—C26 | 1.4985 (19) |
C6—H6 | 0.9500 | C25—H25A | 0.9900 |
C7—C8 | 1.3839 (16) | C25—H25B | 0.9900 |
C8—C9 | 1.4277 (16) | C26—H26A | 0.9800 |
C8—C18 | 1.5129 (15) | C26—H26B | 0.9800 |
C9—C10 | 1.4331 (15) | C26—H26C | 0.9800 |
C11—C12 | 1.4886 (15) | C27—C28 | 1.4952 (19) |
C12—C17 | 1.3842 (17) | C27—H27A | 0.9900 |
C12—C13 | 1.3886 (15) | C27—H27B | 0.9900 |
C13—C14 | 1.3839 (17) | C28—H28A | 0.9800 |
C13—H13 | 0.9500 | C28—H28B | 0.9800 |
C14—C15 | 1.373 (2) | C28—H28C | 0.9800 |
C14—H14 | 0.9500 | ||
C2—O1—C25 | 118.78 (9) | C17—C16—H16 | 120.0 |
C7—O2—C27 | 119.05 (10) | C16—C17—C12 | 120.17 (12) |
C2—C1—C9 | 120.12 (10) | C16—C17—H17 | 119.9 |
C2—C1—C11 | 117.05 (10) | C12—C17—H17 | 119.9 |
C9—C1—C11 | 122.29 (10) | O4—C18—C19 | 121.56 (10) |
O1—C2—C1 | 115.67 (10) | O4—C18—C8 | 118.61 (10) |
O1—C2—C3 | 122.57 (10) | C19—C18—C8 | 119.83 (9) |
C1—C2—C3 | 121.66 (11) | C20—C19—C24 | 119.00 (11) |
C4—C3—C2 | 119.15 (11) | C20—C19—C18 | 122.01 (10) |
C4—C3—H3 | 120.4 | C24—C19—C18 | 118.96 (10) |
C2—C3—H3 | 120.4 | C21—C20—C19 | 120.60 (11) |
C3—C4—C10 | 121.70 (11) | C21—C20—H20 | 119.7 |
C3—C4—H4 | 119.1 | C19—C20—H20 | 119.7 |
C10—C4—H4 | 119.1 | C22—C21—C20 | 119.74 (12) |
C6—C5—C10 | 121.79 (11) | C22—C21—H21 | 120.1 |
C6—C5—H5 | 119.1 | C20—C21—H21 | 120.1 |
C10—C5—H5 | 119.1 | C21—C22—C23 | 120.31 (12) |
C5—C6—C7 | 119.08 (11) | C21—C22—H22 | 119.8 |
C5—C6—H6 | 120.5 | C23—C22—H22 | 119.8 |
C7—C6—H6 | 120.5 | C22—C23—C24 | 119.87 (12) |
O2—C7—C8 | 115.47 (10) | C22—C23—H23 | 120.1 |
O2—C7—C6 | 122.95 (11) | C24—C23—H23 | 120.1 |
C8—C7—C6 | 121.56 (11) | C23—C24—C19 | 120.46 (12) |
C7—C8—C9 | 120.10 (10) | C23—C24—H24 | 119.8 |
C7—C8—C18 | 116.25 (10) | C19—C24—H24 | 119.8 |
C9—C8—C18 | 123.15 (10) | O1—C25—C26 | 106.80 (10) |
C8—C9—C1 | 124.53 (10) | O1—C25—H25A | 110.4 |
C8—C9—C10 | 117.78 (10) | C26—C25—H25A | 110.4 |
C1—C9—C10 | 117.69 (10) | O1—C25—H25B | 110.4 |
C5—C10—C4 | 120.66 (11) | C26—C25—H25B | 110.4 |
C5—C10—C9 | 119.65 (11) | H25A—C25—H25B | 108.6 |
C4—C10—C9 | 119.69 (11) | C25—C26—H26A | 109.5 |
O3—C11—C12 | 121.04 (10) | C25—C26—H26B | 109.5 |
O3—C11—C1 | 118.37 (9) | H26A—C26—H26B | 109.5 |
C12—C11—C1 | 120.57 (9) | C25—C26—H26C | 109.5 |
C17—C12—C13 | 119.30 (11) | H26A—C26—H26C | 109.5 |
C17—C12—C11 | 118.99 (10) | H26B—C26—H26C | 109.5 |
C13—C12—C11 | 121.71 (10) | O2—C27—C28 | 107.10 (11) |
C14—C13—C12 | 120.42 (12) | O2—C27—H27A | 110.3 |
C14—C13—H13 | 119.8 | C28—C27—H27A | 110.3 |
C12—C13—H13 | 119.8 | O2—C27—H27B | 110.3 |
C15—C14—C13 | 119.82 (12) | C28—C27—H27B | 110.3 |
C15—C14—H14 | 120.1 | H27A—C27—H27B | 108.5 |
C13—C14—H14 | 120.1 | C27—C28—H28A | 109.5 |
C14—C15—C16 | 120.36 (12) | C27—C28—H28B | 109.5 |
C14—C15—H15 | 119.8 | H28A—C28—H28B | 109.5 |
C16—C15—H15 | 119.8 | C27—C28—H28C | 109.5 |
C15—C16—C17 | 119.93 (13) | H28A—C28—H28C | 109.5 |
C15—C16—H16 | 120.0 | H28B—C28—H28C | 109.5 |
C25—O1—C2—C1 | −161.30 (10) | C2—C1—C11—O3 | −108.29 (12) |
C25—O1—C2—C3 | 22.47 (15) | C9—C1—C11—O3 | 63.28 (14) |
C9—C1—C2—O1 | −176.52 (9) | C2—C1—C11—C12 | 70.21 (13) |
C11—C1—C2—O1 | −4.75 (14) | C9—C1—C11—C12 | −118.21 (11) |
C9—C1—C2—C3 | −0.25 (16) | O3—C11—C12—C17 | 1.58 (17) |
C11—C1—C2—C3 | 171.51 (10) | C1—C11—C12—C17 | −176.88 (11) |
O1—C2—C3—C4 | 175.92 (10) | O3—C11—C12—C13 | −178.72 (11) |
C1—C2—C3—C4 | −0.08 (16) | C1—C11—C12—C13 | 2.81 (16) |
C2—C3—C4—C10 | 0.64 (17) | C17—C12—C13—C14 | 0.74 (19) |
C10—C5—C6—C7 | 0.25 (18) | C11—C12—C13—C14 | −178.95 (11) |
C27—O2—C7—C8 | 164.97 (11) | C12—C13—C14—C15 | 0.0 (2) |
C27—O2—C7—C6 | −13.53 (17) | C13—C14—C15—C16 | −0.6 (2) |
C5—C6—C7—O2 | 176.45 (11) | C14—C15—C16—C17 | 0.4 (2) |
C5—C6—C7—C8 | −1.97 (18) | C15—C16—C17—C12 | 0.3 (2) |
O2—C7—C8—C9 | −176.28 (9) | C13—C12—C17—C16 | −0.9 (2) |
C6—C7—C8—C9 | 2.25 (17) | C11—C12—C17—C16 | 178.82 (13) |
O2—C7—C8—C18 | −4.12 (14) | C7—C8—C18—O4 | −105.71 (12) |
C6—C7—C8—C18 | 174.41 (10) | C9—C8—C18—O4 | 66.19 (14) |
C7—C8—C9—C1 | 178.17 (10) | C7—C8—C18—C19 | 73.69 (13) |
C18—C8—C9—C1 | 6.58 (16) | C9—C8—C18—C19 | −114.42 (12) |
C7—C8—C9—C10 | −0.83 (15) | O4—C18—C19—C20 | −176.90 (11) |
C18—C8—C9—C10 | −172.42 (9) | C8—C18—C19—C20 | 3.72 (16) |
C2—C1—C9—C8 | −178.97 (10) | O4—C18—C19—C24 | 1.44 (17) |
C11—C1—C9—C8 | 9.71 (16) | C8—C18—C19—C24 | −177.94 (11) |
C2—C1—C9—C10 | 0.03 (14) | C24—C19—C20—C21 | 0.84 (18) |
C11—C1—C9—C10 | −171.29 (9) | C18—C19—C20—C21 | 179.18 (11) |
C6—C5—C10—C4 | −179.28 (11) | C19—C20—C21—C22 | −0.3 (2) |
C6—C5—C10—C9 | 1.12 (17) | C20—C21—C22—C23 | −0.6 (2) |
C3—C4—C10—C5 | 179.54 (11) | C21—C22—C23—C24 | 0.9 (2) |
C3—C4—C10—C9 | −0.86 (17) | C22—C23—C24—C19 | −0.3 (2) |
C8—C9—C10—C5 | −0.82 (15) | C20—C19—C24—C23 | −0.53 (19) |
C1—C9—C10—C5 | −179.89 (10) | C18—C19—C24—C23 | −178.92 (12) |
C8—C9—C10—C4 | 179.57 (10) | C2—O1—C25—C26 | 165.89 (11) |
C1—C9—C10—C4 | 0.50 (15) | C7—O2—C27—C28 | −171.15 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···O3i | 0.95 | 2.37 | 3.2404 (16) | 153 |
C21—H21···O4ii | 0.95 | 2.39 | 3.3326 (16) | 171 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C28H24O4 |
Mr | 424.47 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 193 |
a, b, c (Å) | 7.92185 (14), 20.6794 (4), 14.2130 (3) |
β (°) | 106.043 (1) |
V (Å3) | 2237.68 (7) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.67 |
Crystal size (mm) | 0.60 × 0.50 × 0.10 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Numerical (NUMABS; Higashi, 1999) |
Tmin, Tmax | 0.689, 0.936 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 39782, 4076, 3736 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.091, 1.05 |
No. of reflections | 4076 |
No. of parameters | 292 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.16 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), IL MILIONE (Burla et al., 2007), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···O3i | 0.95 | 2.37 | 3.2404 (16) | 153 |
C21—H21···O4ii | 0.95 | 2.39 | 3.3326 (16) | 171 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
Acknowledgements
The authors express their gratitude to Professor Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture & Technology, for technical advice. This work was partially supported by the Ogasawara Foundation for the Promotion of Science & Engineering, Tokyo, Japan.
References
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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.
In the course of our study on selective electrophilic aromatic aroylation of naphthalene ring core, 1,8-diaroylnaphthalene compounds have proved to be formed regioselectively by the aid of a suitable acidic mediator (Okamoto & Yonezawa, 2009, Okamoto et al., 2011). Recently, we have reported the X-ray crystal structure of 1,8-diaroyled 2,7-dimethoxynaphthalene derivatives such as 1,8-bis(4-aminobenzoyl)-2,7-dimethoxynaphthalene (Nishijima et al., 2010), [8-(4-butoxybenzoyl)-2,7-dimethoxynaphthalen-1-yl](4-butoxyphenyl)methanone [1,8-bis(4-butoxybenzoyl)-2,7-dimethoxynaphthalene] (Sasagawa et al., 2011), [2,7-dimethoxy-8-(2-naphthoyl)naphthalene-1-yl](naphthalene-2-yl)methanone [2,7-dimethoxy-1,8-bis(2-naphthoyl)naphthalene] (Tsumuki et al., 2011), and (3,5-dimethylphenyl)[8-(3,5-dimethylbenzoyl)-2,7-dimethoxynaphthalen-1-yl]methanone (Muto et al., 2012). The simplest molecule in these analogues, 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema et al., 2008), lies across a crystallographic 2-fold axis and the molecular packing is stabilized by C—H···O interactions between carbonyl groups and benzene ring and π···π interactions between benzene rings. As a part of our ongoing studies on the molecular structures of these kinds of homologous molecules, the X-ray crystal structure of the title compound, is reported on herein.
The molecule structure of the title molecule is illustrated in Fig. 1. The two benzoyl groups are situated in an (anti)-orientation and twisted away from the attached naphthalene ring. The dihedral angle between the planes of the two benzene rings (C12-C17 & C19-C24) is 20.03 (7)°. The dihedral angles between these benzene rings and the naphthalene (C1-C10) ring are 68.42 (5)° and 71.69 (5)°. These dihedral angles are similar to that reported for 1,8-dibenzoyl-2,7-dimethoxynaphthalene [80.25 (6)°; Nakaema et al., 2008]. The torsion angles between the carbonyl groups and the naphthalene ring are -63.28 (14)° [C9—C1—C11—O3] and -66.19 (14)° [C9—C8—C18—O4]. The C═O groups lie almost in the plane of the attached benzene ring with torsion angles equal to 1.58 (17)° [O3—C11—C12—C17] and 1.44 (17)° [O4—C18—C19—C24].
In the crystal, the molecular packing of the title compound is mainly stabilized by two types of C—H···O interactions involving adjacent molecules and leading to the formation of chains along the a axis (Table 1 and Fig. 2).