Literature DB >> 23476613

{2,7-Dimeth-oxy-8-[4-(propan-2-yl-oxy)benzo-yl]naphthalen-1-yl}[4-(propan-2-yl-oxy)phen-yl]methanone.

Kosuke Sasagawa1, Ryo Takeuchi, Taro Kusakabe, Noriyuki Yonezawa, Akiko Okamoto.   

Abstract

The title compound, C32H32O6, crystallized with two independent molecules in the asymmetric unit. Each molecule has essentially the same feature of non-coplanar aromatic rings whereby the two 4-isopropoxybenzoyl groups are twisted in a perpendicular manner to the naphthalene ring and oriented in the same direction (syn-orientation). The benzene rings of the aroyl groups make dihedral angles of 16.13 (7) and 25.31 (7)° in the two molecules. These benzene rings make dihedral angles of 88.38 (8) and 75.32 (7)° with the naphthalene ring system in one molecule, and 89.71 (7) and 82.11 (7)° in the other. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming a three-dimensional network. In one independent molecule, the 2-propyl groups of both isoprop-oxy groups are disordered over two positions with site occupancies of 0.512 (3) and 0.488 (3).

Entities:  

Year:  2013        PMID： 23476613      PMCID： PMC3588464          DOI： 10.1107/S1600536813004959

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the synthesis of aroylated naphthalene compounds via electrophilic aromatic substitution of naphthalene derivatives, see: Okamoto & Yonezawa (2009 ▶); Okamoto et al. (2011 ▶). For structures of closely related compounds, see: Hijikata et al. (2010 ▶); Sasagawa et al. (2011 ▶, 2012a ▶,b ▶, 2013 ▶).

Experimental

Crystal data

C32H32O6 M = 512.58 Monoclinic, a = 10.9988 (2) Å b = 25.8702 (5) Å c = 19.2062 (4) Å β = 100.338 (1)° V = 5376.27 (17) Å3 Z = 8 Cu Kα radiation μ = 0.70 mm−1 T = 193 K 0.40 × 0.30 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.766, T max = 0.872 98899 measured reflections 9839 independent reflections 8263 reflections with I > 2σ(I) R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.121 S = 0.94 9839 reflections 748 parameters 9 restraints H-atom parameters constrained Δρmax = 0.27 e Å−3 Δρmin = −0.22 e Å−3 Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97. Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813004959/su2564sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004959/su2564Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813004959/su2564Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C32H32O6F(000) = 2176
Mr = 512.58Dx = 1.267 Mg m−3
Monoclinic, P21/nCu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ynCell parameters from 83451 reflections
a = 10.9988 (2) Åθ = 3.4–68.2°
b = 25.8702 (5) ŵ = 0.70 mm−1
c = 19.2062 (4) ÅT = 193 K
β = 100.338 (1)°Plate, colourless
V = 5376.27 (17) Å30.40 × 0.30 × 0.20 mm
Z = 8
Rigaku R-AXIS RAPID diffractometer9839 independent reflections
Radiation source: fine-focus sealed tube8263 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
Detector resolution: 10.000 pixels mm-1θmax = 68.2°, θmin = 3.4°
ω scansh = −13→13
Absorption correction: numerical (NUMABS; Higashi, 1999)k = −31→31
Tmin = 0.766, Tmax = 0.872l = −23→23
98899 measured reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.121w = 1/[σ2(Fo2) + (0.0715P)2 + 1.6612P] where P = (Fo2 + 2Fc2)/3
S = 0.94(Δ/σ)max = 0.001
9839 reflectionsΔρmax = 0.27 e Å−3
748 parametersΔρmin = −0.22 e Å−3
9 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00071 (6)
Experimental. Spectroscopic data for the title compound:1H NMR δ (300 MHz, CDCl3);0.74(12H, s), 3.71(6H, s), 4.59(2H, m), 6.76(4H, br), 7.19(2H, d, J = 9.3 Hz), 7.63(4H, br), 7.92(2H, d, J = 9.3 Hz) p.p.m.. 13C NMR δ (100 MHz, CDCl3); 21.80, 30.70, 56.23, 69.56, 111.00, 114.20, 121.54, 125.24, 129.28, 131.32, 131.58, 155.71, 161.46, 194.86 p.p.m.. IR (KBr, cm-1); 1663(Ar, naphthalene), 1598(C=O), 1510(Ar, naphthalene). HRMS (m/z); [M + H]+ Calcd for C32H33O6, 513.2285; found, 513.2285
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles
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 > 2σ(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.
xyzUiso*/UeqOcc. (<1)
O10.60693 (10)0.72303 (4)0.36326 (6)0.0497 (4)
O20.48829 (10)0.74405 (4)0.21488 (6)0.0467 (4)
O30.86555 (11)0.68059 (5)0.42031 (6)0.0554 (4)
O40.54422 (11)0.70364 (4)0.06137 (5)0.0512 (4)
O50.90620 (12)0.92918 (5)0.32676 (12)0.0954 (7)
O60.74253 (11)0.93487 (4)0.08944 (7)0.0544 (4)
C10.76067 (13)0.68814 (5)0.30413 (7)0.0361 (4)
C20.84952 (14)0.66254 (6)0.35207 (8)0.0425 (5)
C30.91844 (15)0.62125 (6)0.33124 (9)0.0483 (5)
C40.89840 (15)0.60671 (6)0.26233 (9)0.0475 (5)
C50.81015 (14)0.63187 (5)0.21088 (8)0.0408 (5)
C60.79227 (15)0.61570 (6)0.13952 (9)0.0474 (5)
C70.70616 (16)0.63802 (6)0.08864 (9)0.0484 (5)
C80.63481 (14)0.67918 (6)0.10793 (8)0.0411 (5)
C90.65217 (13)0.69810 (5)0.17632 (7)0.0346 (4)
C100.73873 (13)0.67378 (5)0.23110 (7)0.0348 (4)
C110.69586 (13)0.73178 (6)0.33529 (7)0.0372 (4)
C120.74894 (13)0.78416 (5)0.33299 (7)0.0356 (4)
C130.85671 (13)0.79273 (6)0.30592 (8)0.0389 (4)
C140.90612 (14)0.84140 (6)0.30505 (9)0.0461 (5)
C150.84830 (15)0.88319 (6)0.33003 (11)0.0551 (6)
C160.73928 (15)0.87583 (6)0.35594 (10)0.0521 (5)
C170.69173 (14)0.82654 (6)0.35791 (8)0.0437 (5)
C180.57814 (13)0.74625 (5)0.18612 (7)0.0351 (4)
C190.61980 (12)0.79548 (5)0.15887 (7)0.0338 (4)
C200.72121 (13)0.79873 (6)0.12430 (8)0.0385 (4)
C210.75761 (14)0.84540 (6)0.10076 (8)0.0412 (5)
C220.69634 (14)0.89068 (6)0.11305 (8)0.0408 (5)
C230.59485 (14)0.88847 (6)0.14727 (8)0.0410 (5)
C240.55734 (13)0.84092 (6)0.16882 (7)0.0373 (4)
C250.96293 (16)0.65966 (8)0.47107 (9)0.0566 (6)
C260.5251 (2)0.69005 (8)−0.01125 (9)0.0681 (7)
C270.8623 (6)0.9742 (2)0.3725 (6)0.083 (3)0.512 (3)
C280.8710 (8)0.9676 (3)0.4514 (4)0.118 (3)0.512 (3)
C290.9435 (5)1.01873 (17)0.3551 (4)0.096 (2)0.512 (3)
C300.69254 (19)0.98401 (7)0.10301 (13)0.0672 (7)
C310.7586 (14)1.0240 (5)0.0743 (8)0.106 (5)0.512 (3)
C320.5743 (4)0.98772 (14)0.0342 (2)0.0628 (11)0.512 (3)
C29'0.9072 (5)1.01823 (16)0.2926 (3)0.0723 (18)0.488 (3)
C27'0.8509 (7)0.9777 (2)0.3317 (3)0.0587 (18)0.488 (3)
C28'0.8944 (7)0.9823 (3)0.4114 (5)0.087 (3)0.488 (3)
C31'0.7574 (5)0.98833 (17)0.1920 (3)0.0820 (14)0.488 (3)
C32'0.7797 (13)1.0236 (4)0.0810 (6)0.061 (2)0.488 (3)
O70.52631 (10)0.99841 (4)0.31284 (6)0.0509 (4)
O80.40037 (10)1.00696 (4)0.16112 (6)0.0510 (4)
O90.45137 (14)1.04647 (5)0.43687 (6)0.0718 (5)
O100.11665 (12)1.04293 (5)0.07925 (6)0.0604 (4)
O110.20901 (10)0.80048 (4)0.35548 (6)0.0469 (3)
O120.05574 (10)0.81001 (4)0.08665 (6)0.0463 (3)
C330.33939 (14)1.04269 (5)0.32204 (8)0.0387 (4)
C340.35879 (17)1.06694 (6)0.38724 (8)0.0502 (5)
C350.28477 (19)1.10852 (6)0.40178 (9)0.0575 (6)
C360.19387 (17)1.12627 (6)0.35009 (9)0.0511 (6)
C370.17281 (14)1.10447 (5)0.28170 (8)0.0412 (4)
C380.08108 (15)1.12542 (6)0.22844 (9)0.0472 (5)
C390.05962 (15)1.10602 (6)0.16186 (9)0.0495 (5)
C400.13021 (15)1.06377 (6)0.14563 (8)0.0439 (5)
C410.22066 (13)1.04114 (5)0.19615 (8)0.0368 (4)
C420.24586 (13)1.06143 (5)0.26639 (7)0.0355 (4)
C430.41773 (13)0.99499 (5)0.31764 (7)0.0374 (4)
C440.35907 (12)0.94405 (5)0.32422 (7)0.0337 (4)
C450.25260 (13)0.93868 (5)0.35358 (7)0.0376 (4)
C460.20605 (13)0.89039 (6)0.36397 (8)0.0401 (5)
C470.26250 (13)0.84606 (5)0.34327 (8)0.0379 (4)
C480.36787 (13)0.85103 (5)0.31252 (8)0.0391 (4)
C490.41534 (13)0.89952 (5)0.30440 (7)0.0365 (4)
C500.29425 (13)0.99896 (5)0.16853 (7)0.0379 (4)
C510.23169 (13)0.94911 (5)0.14746 (7)0.0357 (4)
C520.12774 (13)0.93272 (6)0.17363 (7)0.0386 (4)
C530.07346 (14)0.88584 (6)0.15349 (8)0.0413 (5)
C540.11889 (13)0.85469 (5)0.10467 (7)0.0382 (4)
C550.22100 (14)0.87104 (6)0.07710 (8)0.0419 (5)
C560.27687 (13)0.91749 (6)0.09950 (8)0.0404 (5)
C570.4899 (3)1.07333 (9)0.50069 (11)0.0873 (9)
C580.05196 (17)1.07207 (7)0.02149 (9)0.0539 (6)
C590.24601 (16)0.75272 (6)0.32414 (9)0.0478 (5)
C600.19015 (19)0.71001 (7)0.36188 (12)0.0653 (7)
C610.19847 (18)0.75223 (7)0.24587 (10)0.0592 (6)
C620.08681 (16)0.77827 (6)0.02938 (9)0.0510 (6)
C630.2018 (2)0.74668 (7)0.05348 (12)0.0681 (7)
C64−0.0252 (2)0.74458 (9)0.00674 (12)0.0778 (8)
H30.978100.603800.365000.0580*
H160.697900.904400.372100.0630*
H170.618400.821500.376700.0520*
H200.765500.768300.117000.0460*
H210.824900.846800.076000.0490*
H230.552100.919100.155700.0490*
H240.486900.839200.191000.0450*
H25A1.041000.662500.453500.0680*
H25B0.945800.623200.479200.0680*
H25C0.969200.678800.515600.0680*
H26A0.501500.65350−0.016700.0820*
H26B0.601600.69570−0.029700.0820*
H26C0.459100.71150−0.037600.0820*
H270.774500.982600.351700.0990*0.512 (3)
H28A0.958100.967800.474500.1770*0.512 (3)
H28B0.833100.934700.461000.1770*0.512 (3)
H28C0.827600.996100.470000.1770*0.512 (3)
H29A0.909201.051600.367800.1440*0.512 (3)
H29B0.946001.018500.304300.1440*0.512 (3)
H29C1.027501.014600.382000.1440*0.512 (3)
H300.673100.989800.151300.0810*0.512 (3)
H31A0.847701.018600.089300.1580*0.512 (3)
H31B0.735501.057700.091400.1580*0.512 (3)
H31C0.737901.023200.022500.1580*0.512 (3)
H32A0.531601.020800.035800.0950*0.512 (3)
H32B0.516400.959300.036900.0950*0.512 (3)
H32C0.606100.98520−0.010200.0950*0.512 (3)
H40.944900.578900.248200.0570*
H60.841800.588500.126700.0570*
H70.694300.626100.041100.0580*
H130.896500.764500.287800.0470*
H140.980400.846400.287200.0550*
H27'0.758800.976500.318200.0710*0.488 (3)
H28D0.865700.952200.435000.1290*0.488 (3)
H28E0.860401.013900.428600.1290*0.488 (3)
H28F0.984800.983700.421900.1290*0.488 (3)
H29D0.997401.015100.303200.1090*0.488 (3)
H29E0.882901.052500.307100.1090*0.488 (3)
H29F0.878201.013900.241600.1090*0.488 (3)
H30'0.601500.989600.088600.0810*0.488 (3)
H31D0.847000.983500.197900.1240*0.488 (3)
H31E0.722100.961500.218400.1240*0.488 (3)
H31F0.739801.022400.210000.1240*0.488 (3)
H32D0.793601.015700.033200.0920*0.488 (3)
H32E0.858601.022600.114100.0920*0.488 (3)
H32F0.743201.058100.081600.0920*0.488 (3)
H350.298301.124000.447400.0690*
H360.143201.154000.360200.0610*
H380.033201.153800.239500.0570*
H39−0.002301.120700.126600.0590*
H450.211800.968600.366500.0450*
H460.135000.887300.385400.0480*
H480.406400.821300.297400.0470*
H490.488400.902600.284800.0440*
H520.094100.954100.205600.0460*
H530.004500.874600.173000.0500*
H550.252100.850500.043200.0500*
H560.348100.928100.081600.0480*
H57A0.564801.057200.527000.1050*
H57B0.424301.072100.529100.1050*
H57C0.507301.109400.490400.1050*
H58A0.087801.106800.022000.0650*
H58B−0.035301.074700.025700.0650*
H58C0.058801.05480−0.023100.0650*
H590.338100.749600.333600.0570*
H60A0.100300.714400.354600.0780*
H60B0.224300.711400.412600.0780*
H60C0.209700.676500.342900.0780*
H61A0.233600.781500.223800.0710*
H61B0.108200.755000.237000.0710*
H61C0.222600.719800.225700.0710*
H620.099100.80100−0.010900.0610*
H63A0.222900.727700.013100.0820*
H63B0.187000.722100.089900.0820*
H63C0.270200.769700.073100.0820*
H64A−0.011700.72220−0.032300.0930*
H64B−0.097800.76640−0.008900.0930*
H64C−0.039000.723200.046700.0930*
U11U22U33U12U13U23
O10.0479 (6)0.0540 (7)0.0511 (6)−0.0050 (5)0.0194 (5)−0.0014 (5)
O20.0460 (6)0.0422 (6)0.0571 (7)0.0044 (5)0.0237 (5)0.0090 (5)
O30.0588 (7)0.0622 (7)0.0397 (6)0.0104 (6)−0.0059 (5)0.0021 (5)
O40.0594 (7)0.0569 (7)0.0343 (5)0.0094 (5)0.0006 (5)−0.0043 (5)
O50.0495 (8)0.0346 (6)0.2053 (19)0.0011 (5)0.0312 (10)−0.0029 (9)
O60.0569 (7)0.0397 (6)0.0732 (8)0.0000 (5)0.0297 (6)0.0121 (5)
C10.0353 (7)0.0328 (7)0.0395 (7)−0.0020 (6)0.0049 (6)0.0029 (6)
C20.0430 (8)0.0401 (8)0.0430 (8)−0.0006 (6)0.0039 (7)0.0040 (6)
C30.0433 (9)0.0426 (8)0.0565 (10)0.0061 (7)0.0020 (7)0.0092 (7)
C40.0451 (9)0.0353 (8)0.0623 (10)0.0073 (6)0.0102 (7)0.0020 (7)
C50.0420 (8)0.0318 (7)0.0496 (9)0.0004 (6)0.0109 (7)−0.0001 (6)
C60.0532 (10)0.0379 (8)0.0533 (9)0.0041 (7)0.0159 (8)−0.0065 (7)
C70.0602 (10)0.0440 (8)0.0423 (8)0.0000 (7)0.0131 (7)−0.0095 (7)
C80.0453 (8)0.0405 (8)0.0374 (8)−0.0003 (6)0.0071 (6)0.0001 (6)
C90.0359 (7)0.0325 (7)0.0362 (7)−0.0005 (6)0.0088 (6)0.0008 (5)
C100.0345 (7)0.0300 (7)0.0408 (8)−0.0021 (5)0.0091 (6)0.0014 (5)
C110.0357 (8)0.0443 (8)0.0307 (7)0.0011 (6)0.0035 (6)0.0015 (6)
C120.0353 (7)0.0400 (7)0.0301 (7)0.0025 (6)0.0020 (5)−0.0001 (6)
C130.0391 (8)0.0395 (8)0.0379 (7)0.0040 (6)0.0066 (6)−0.0009 (6)
C140.0384 (8)0.0431 (8)0.0565 (9)0.0002 (6)0.0081 (7)0.0047 (7)
C150.0380 (9)0.0371 (8)0.0872 (13)0.0013 (6)0.0035 (8)0.0014 (8)
C160.0447 (9)0.0410 (8)0.0688 (11)0.0083 (7)0.0050 (8)−0.0094 (8)
C170.0378 (8)0.0464 (8)0.0470 (8)0.0056 (6)0.0079 (6)−0.0026 (7)
C180.0359 (7)0.0384 (7)0.0308 (7)0.0021 (6)0.0056 (6)0.0014 (5)
C190.0339 (7)0.0374 (7)0.0299 (7)0.0021 (6)0.0054 (5)0.0025 (5)
C200.0359 (7)0.0399 (8)0.0406 (8)0.0045 (6)0.0095 (6)0.0019 (6)
C210.0365 (8)0.0456 (8)0.0440 (8)0.0003 (6)0.0140 (6)0.0039 (6)
C220.0404 (8)0.0396 (8)0.0431 (8)−0.0014 (6)0.0091 (6)0.0067 (6)
C230.0429 (8)0.0375 (8)0.0443 (8)0.0053 (6)0.0126 (6)0.0050 (6)
C240.0371 (8)0.0405 (7)0.0362 (7)0.0037 (6)0.0114 (6)0.0036 (6)
C250.0479 (10)0.0733 (12)0.0451 (9)−0.0020 (8)−0.0011 (7)0.0128 (8)
C260.0855 (14)0.0795 (13)0.0354 (9)0.0124 (11)0.0005 (9)−0.0048 (8)
C270.049 (3)0.039 (3)0.153 (9)0.005 (2)−0.001 (5)0.001 (4)
C280.123 (5)0.116 (6)0.121 (6)−0.031 (4)0.039 (5)−0.059 (5)
C290.073 (3)0.046 (2)0.166 (6)0.004 (2)0.011 (4)−0.015 (3)
C300.0615 (11)0.0407 (9)0.1052 (14)−0.0021 (8)0.0305 (10)0.0008 (10)
C310.093 (7)0.073 (6)0.171 (10)0.023 (4)0.079 (7)0.057 (5)
C320.071 (2)0.0461 (19)0.079 (2)−0.0026 (17)0.0342 (12)0.0125 (17)
C29'0.077 (3)0.041 (2)0.104 (4)0.0067 (19)0.030 (3)0.009 (2)
C27'0.058 (3)0.036 (2)0.083 (4)0.0097 (17)0.015 (3)0.008 (2)
C28'0.092 (5)0.071 (4)0.098 (6)−0.008 (4)0.021 (4)−0.015 (4)
C31'0.082 (3)0.051 (2)0.112 (2)0.002 (2)0.015 (2)−0.009 (2)
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C58—O10—C40—C41−163.06 (14)C43—C33—C34—C35−173.55 (15)
C59—O11—C47—C48−11.9 (2)C34—C33—C42—C37−1.7 (2)
C47—O11—C59—C60167.64 (14)C34—C33—C42—C41177.20 (15)
C59—O11—C47—C46168.50 (13)C43—C33—C42—C37174.46 (13)
C47—O11—C59—C61−71.65 (18)C43—C33—C42—C41−6.6 (2)
C62—O12—C54—C53172.24 (13)C34—C33—C43—O7−76.67 (18)
C62—O12—C54—C55−6.4 (2)C34—C33—C43—C4499.37 (16)
C54—O12—C62—C64−160.28 (14)C42—C33—C43—O7106.99 (17)
C54—O12—C62—C6378.51 (17)C42—C33—C43—C44−76.98 (18)
C10—C1—C2—C3−1.5 (2)O9—C34—C35—C36−179.22 (17)
C11—C1—C2—O3−0.13 (19)C33—C34—C35—C36−1.7 (3)
C10—C1—C2—O3178.01 (13)C34—C35—C36—C37−0.9 (3)
C2—C1—C10—C9−178.23 (14)C35—C36—C37—C38−177.19 (16)
C11—C1—C10—C5179.07 (13)C35—C36—C37—C422.1 (2)
C11—C1—C10—C9−0.3 (2)C36—C37—C38—C39178.93 (16)
C2—C1—C11—O1−84.97 (17)C42—C37—C38—C39−0.3 (2)
C2—C1—C11—C1292.26 (15)C36—C37—C42—C33−0.7 (2)
C11—C1—C2—C3−179.63 (14)C36—C37—C42—C41−179.74 (14)
C2—C1—C10—C51.1 (2)C38—C37—C42—C33178.52 (14)
C10—C1—C11—C12−85.78 (17)C38—C37—C42—C41−0.5 (2)
C10—C1—C11—O196.99 (17)C37—C38—C39—C400.3 (2)
O3—C2—C3—C4−178.53 (15)C38—C39—C40—O10−178.07 (15)
C1—C2—C3—C40.9 (2)C38—C39—C40—C410.5 (2)
C2—C3—C4—C50.0 (2)O10—C40—C41—C42177.33 (13)
C3—C4—C5—C6179.77 (15)O10—C40—C41—C503.2 (2)
C3—C4—C5—C10−0.3 (2)C39—C40—C41—C42−1.4 (2)
C10—C5—C6—C7−1.6 (2)C39—C40—C41—C50−175.50 (14)
C4—C5—C10—C1−0.3 (2)C40—C41—C42—C33−177.63 (14)
C4—C5—C6—C7178.35 (16)C40—C41—C42—C371.3 (2)
C4—C5—C10—C9179.14 (14)C50—C41—C42—C33−4.1 (2)
C6—C5—C10—C1179.69 (14)C50—C41—C42—C37174.83 (13)
C6—C5—C10—C9−0.9 (2)C40—C41—C50—O8106.00 (16)
C5—C6—C7—C81.3 (2)C40—C41—C50—C51−70.86 (17)
C6—C7—C8—C91.6 (2)C42—C41—C50—O8−67.82 (19)
C6—C7—C8—O4−178.65 (15)C42—C41—C50—C51115.32 (15)
O4—C8—C9—C10176.07 (13)O7—C43—C44—C45157.34 (14)
O4—C8—C9—C18−6.44 (19)O7—C43—C44—C49−18.8 (2)
C7—C8—C9—C10−4.2 (2)C33—C43—C44—C45−18.70 (19)
C7—C8—C9—C18173.30 (14)C33—C43—C44—C49165.13 (12)
C18—C9—C10—C15.9 (2)C43—C44—C45—C46−174.88 (13)
C18—C9—C10—C5−173.52 (13)C49—C44—C45—C461.3 (2)
C8—C9—C18—O2105.84 (16)C43—C44—C49—C48176.92 (13)
C8—C9—C10—C1−176.93 (14)C45—C44—C49—C480.6 (2)
C8—C9—C10—C53.7 (2)C44—C45—C46—C47−2.0 (2)
C10—C9—C18—C19103.53 (16)C45—C46—C47—O11−179.63 (13)
C8—C9—C18—C19−73.82 (17)C45—C46—C47—C480.7 (2)
C10—C9—C18—O2−76.80 (19)O11—C47—C48—C49−178.44 (14)
O1—C11—C12—C13174.68 (14)C46—C47—C48—C491.2 (2)
O1—C11—C12—C17−5.5 (2)C47—C48—C49—C44−1.9 (2)
C1—C11—C12—C13−2.50 (19)O8—C50—C51—C52160.32 (14)
C1—C11—C12—C17177.35 (13)O8—C50—C51—C56−20.2 (2)
C13—C12—C17—C160.2 (2)C41—C50—C51—C52−22.86 (19)
C11—C12—C13—C14−179.00 (14)C41—C50—C51—C56156.59 (13)
C17—C12—C13—C141.2 (2)C50—C51—C52—C53−179.08 (13)
C11—C12—C17—C16−179.66 (15)C56—C51—C52—C531.5 (2)
C12—C13—C14—C15−1.1 (2)C50—C51—C56—C55−178.90 (14)
C13—C14—C15—O5179.68 (17)C52—C51—C56—C550.6 (2)
C13—C14—C15—C16−0.2 (3)C51—C52—C53—C54−2.2 (2)
C14—C15—C16—C171.5 (3)C52—C53—C54—O12−177.80 (13)
O5—C15—C16—C17−178.35 (19)C52—C53—C54—C550.9 (2)
C15—C16—C17—C12−1.5 (3)O12—C54—C55—C56179.67 (13)
O2—C18—C19—C20−178.60 (14)C53—C54—C55—C561.1 (2)
O2—C18—C19—C242.5 (2)C54—C55—C56—C51−1.8 (2)
D—H···AD—HH···AD···AD—H···A
C4—H4···O7i0.952.443.3240 (19)155
C38—H38···O2ii0.952.523.3888 (19)152
C62—H62···O1iii1.002.513.238 (2)129
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C4—H4⋯O7i 0.952.443.3240 (19)155
C38—H38⋯O2ii 0.952.523.3888 (19)152
C62—H62⋯O1iii 1.002.513.238 (2)129

Symmetry codes: (i) ; (ii) ; (iii) .

  6 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  2,7-Dimeth-oxy-1,8-bis-(4-phen-oxy-benzo-yl)naphthalene.

Authors:  Daichi Hijikata; Teruhisa Takada; Atsushi Nagasawa; Akiko Okamoto; Noriyuki Yonezawa
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-10-23

3.  [8-(4-But-oxy-benzo-yl)-2,7-dimeth-oxy-naphthalen-1-yl](4-but-oxy-phen-yl)methanone.

Authors:  Kosuke Sasagawa; Toyokazu Muto; Akiko Okamoto; Hideaki Oike; Noriyuki Yonezawa
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-11-19

4.  [2,7-Dimeth-oxy-8-(4-propyl-benzo-yl)naphthalen-1-yl](4-propyl-phen-yl)methanone.

Authors:  Kosuke Sasagawa; Daichi Hijikata; Rei Sakamoto; Akiko Okamoto; Noriyuki Yonezawa
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-07-28

5.  [2,7-Dimeth-oxy-8-(4-meth-oxy-benzo-yl)naphthalen-1-yl](4-meth-oxy-phen-yl)methanone chloro-form monosolvate.

Authors:  Kosuke Sasagawa; Rei Sakamoto; Taro Kusakabe; Akiko Okamoto; Noriyuki Yonezawa
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-12-22

6.  {2,7-Dimeth-oxy-8-[4-(2-methyl-prop-yl)benzo-yl]naphthalen-1-yl}[4-(2-methyl-prop-yl)phen-yl]methanone.

Authors:  Kosuke Sasagawa; Daichi Hijikata; Rei Sakamoto; Akiko Okamoto; Noriyuki Yonezawa
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-11-14
  6 in total
  2 in total

1.  (4-Eth-oxy-benzo-yl)[8-(4-eth-oxy-benzo-yl)-2,7-di-meth-oxy-naphthalen-1-yl]methanone.

Authors:  Kosuke Sasagawa; Rei Sakamoto; Daichi Hijikata; Noriyuki Yonezawa; Akiko Okamoto
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-04-05

2.  1,8-Bis(4-fluoro-benzo-yl)naphthalen-2,7-diyl dimethane-sulfonate.

Authors:  Daichi Hijikata; Rei Sakamoto; Katsuhiro Isozaki; Noriyuki Yonezawa; Akiko Okamoto
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-03-16
  2 in total

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