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The structure of the title compound, C25H24O2, has been determined as part of an ongoing investigation into the biological activity of compounds based on the β-tetralone core. The conformational structure of (I) is stabilized by C—H...π interactions between the aliphatic ring H atoms and the π-electron systems of the benzyl subunits.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802000715/tk6050sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802000715/tk6050Isup2.hkl
Contains datablock I

CCDC reference: 180800

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.052
  • wR factor = 0.174
  • Data-to-parameter ratio = 14.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

HYDTR_01 Extra text has been found in the _refine_ls_hydrogen_treatment field. Explanatory text should be in the _publ_section_refinement field. Hydrogen treatment given as noref' Hydrogen treatment identified as noref

Computing details top

Data collection: MSC/AFC7 Diffractometer Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC7 Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997-2001); program(s) used to solve structure: TEXSAN for Windows; program(s) used to refine structure: TEXSAN for Windows and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN for Windows and PLATON (Spek, 2001).

1,1-Dibenzyl-6-methoxy-3,4-dihydro-1H-naphthalen-2-one top
Crystal data top
C25H24O2F(000) = 760
Mr = 356.44Dx = 1.212 Mg m3
Monoclinic, P21/aMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yabCell parameters from 25 reflections
a = 14.766 (5) Åθ = 17.1–19.7°
b = 11.214 (4) ŵ = 0.08 mm1
c = 12.089 (4) ÅT = 295 K
β = 102.51 (3)°Prismatic, colorless
V = 1954.2 (12) Å30.50 × 0.40 × 0.25 mm
Z = 4
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.029
Radiation source: Rigaku rotating anodeθmax = 25.0°, θmin = 2.5°
Graphite monochromatorh = 178
ω/2θ scansk = 013
3985 measured reflectionsl = 1414
3440 independent reflections3 standard reflections every 150 reflections
2037 reflections with I > 2σ(I) intensity decay: 0.2%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: constr
R[F2 > 2σ(F2)] = 0.052Noref'
wR(F2) = 0.174 w = 1/[σ2(Fo2) + (0.0825P)2 + 0.4084P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
3440 reflectionsΔρmax = 0.50 e Å3
245 parametersΔρmin = 0.31 e Å3
0 restraintsExtinction correction: SHELXL97, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0071 (18)
Special details top

Experimental. The scan width was (1.73 + 0.30tanθ)° with an ω scan speed of 32° per minute (up to 5 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ?

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O211.02963 (13)0.02484 (16)0.33744 (17)0.0706 (7)
O611.02475 (16)0.67149 (17)0.12726 (19)0.0835 (9)
C10.97965 (15)0.2276 (2)0.33735 (19)0.0476 (8)
C21.04057 (17)0.1263 (2)0.3088 (2)0.0558 (9)
C31.1189 (2)0.1596 (3)0.2532 (3)0.0882 (12)
C41.0929 (2)0.2491 (3)0.1641 (3)0.0776 (12)
C51.05616 (19)0.4676 (2)0.1525 (2)0.0632 (10)
C61.01173 (18)0.5673 (2)0.1807 (2)0.0578 (9)
C70.95745 (18)0.5574 (2)0.2599 (2)0.0592 (9)
C80.95043 (18)0.4485 (2)0.3091 (2)0.0580 (9)
C90.99486 (15)0.3464 (2)0.28285 (18)0.0468 (8)
C101.04867 (16)0.3570 (2)0.20146 (19)0.0516 (8)
C110.87638 (17)0.1894 (2)0.2973 (2)0.0555 (9)
C121.00303 (18)0.2360 (2)0.4694 (2)0.0563 (9)
C610.9764 (2)0.7743 (3)0.1501 (3)0.0835 (11)
C1110.84703 (16)0.1662 (2)0.1711 (2)0.0538 (8)
C1120.82696 (17)0.2587 (2)0.0928 (2)0.0603 (9)
C1130.8034 (2)0.2352 (3)0.0217 (3)0.0710 (11)
C1140.7987 (2)0.1208 (3)0.0610 (3)0.0809 (11)
C1150.8175 (2)0.0281 (3)0.0148 (3)0.0867 (12)
C1160.8418 (2)0.0508 (2)0.1302 (3)0.0719 (11)
C1211.10479 (18)0.2512 (2)0.5225 (2)0.0552 (8)
C1221.1526 (2)0.3565 (3)0.5135 (2)0.0684 (10)
C1231.2467 (2)0.3659 (3)0.5627 (3)0.0875 (13)
C1241.2930 (2)0.2718 (5)0.6206 (3)0.1017 (16)
C1251.2468 (3)0.1683 (4)0.6312 (3)0.0998 (14)
C1261.1534 (2)0.1572 (3)0.5824 (2)0.0744 (11)
H3A1.168600.190000.309100.1050*
H3B1.138500.089800.220300.1050*
H4A1.050400.214100.102400.0930*
H4B1.147200.273100.140000.0930*
H51.092900.474700.097400.0760*
H70.925500.624900.279700.0720*
H80.913200.442800.364000.0700*
H11A0.867300.118600.336200.0670*
H11B0.838700.251300.316400.0670*
H12A0.982200.164500.498200.0680*
H12B0.970500.301900.490600.0680*
H61A0.911500.761500.125200.1000*
H61B0.990400.789200.229400.1000*
H61C0.994500.840500.111400.1000*
H1120.829200.339100.118600.0720*
H1130.790000.299300.074100.0850*
H1140.783000.105500.140300.0970*
H1150.813300.051500.012500.1050*
H1160.855100.014200.181700.0860*
H1221.120800.423000.473900.0810*
H1231.279300.438300.556300.1060*
H1241.357800.278600.653800.1210*
H1251.279300.103100.672400.1190*
H1261.122000.084500.590100.0880*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O210.0693 (12)0.0549 (12)0.0843 (14)0.0047 (9)0.0097 (10)0.0031 (10)
O610.1051 (17)0.0609 (13)0.0925 (15)0.0066 (11)0.0387 (13)0.0123 (11)
C10.0433 (13)0.0529 (14)0.0480 (13)0.0003 (11)0.0127 (10)0.0008 (10)
C20.0523 (15)0.0583 (17)0.0539 (14)0.0031 (12)0.0050 (11)0.0031 (12)
C30.089 (2)0.085 (2)0.103 (2)0.0280 (18)0.048 (2)0.0056 (19)
C40.080 (2)0.078 (2)0.087 (2)0.0118 (16)0.0446 (18)0.0001 (17)
C50.0629 (16)0.0694 (18)0.0639 (16)0.0087 (14)0.0281 (13)0.0011 (14)
C60.0627 (16)0.0531 (14)0.0560 (15)0.0082 (13)0.0096 (12)0.0009 (12)
C70.0669 (17)0.0549 (15)0.0565 (15)0.0060 (13)0.0146 (13)0.0043 (12)
C80.0645 (16)0.0584 (16)0.0573 (15)0.0063 (13)0.0268 (13)0.0009 (12)
C90.0428 (13)0.0541 (14)0.0437 (13)0.0015 (11)0.0098 (10)0.0019 (10)
C100.0453 (14)0.0594 (15)0.0524 (14)0.0016 (11)0.0154 (11)0.0055 (12)
C110.0466 (14)0.0591 (15)0.0615 (16)0.0007 (11)0.0134 (11)0.0074 (12)
C120.0566 (15)0.0634 (16)0.0507 (14)0.0001 (12)0.0158 (12)0.0028 (12)
C610.098 (2)0.0568 (17)0.089 (2)0.0027 (17)0.0055 (18)0.0076 (15)
C1110.0377 (13)0.0601 (15)0.0614 (15)0.0037 (11)0.0059 (11)0.0042 (12)
C1120.0459 (14)0.0650 (16)0.0676 (17)0.0011 (12)0.0073 (12)0.0057 (13)
C1130.0589 (17)0.083 (2)0.0677 (18)0.0017 (15)0.0061 (14)0.0150 (16)
C1140.078 (2)0.096 (2)0.0628 (18)0.0031 (18)0.0022 (15)0.0049 (18)
C1150.097 (2)0.076 (2)0.078 (2)0.0094 (18)0.0012 (18)0.0123 (17)
C1160.0733 (19)0.0605 (17)0.0742 (19)0.0086 (14)0.0008 (14)0.0040 (14)
C1210.0577 (15)0.0659 (16)0.0431 (13)0.0026 (13)0.0135 (11)0.0061 (12)
C1220.077 (2)0.0763 (19)0.0527 (15)0.0148 (15)0.0161 (14)0.0098 (14)
C1230.079 (2)0.125 (3)0.0596 (18)0.041 (2)0.0177 (17)0.0198 (19)
C1240.058 (2)0.174 (4)0.067 (2)0.009 (2)0.0002 (16)0.009 (2)
C1250.079 (2)0.130 (3)0.079 (2)0.012 (2)0.0081 (18)0.009 (2)
C1260.0711 (19)0.083 (2)0.0629 (17)0.0015 (16)0.0012 (15)0.0039 (15)
Geometric parameters (Å, º) top
O21—C21.210 (3)C111—C1161.382 (3)
O61—C61.369 (3)C11—H11B0.9489
O61—C611.414 (4)C112—C1131.378 (4)
C1—C21.534 (3)C12—H12B0.9465
C1—C91.524 (3)C12—H12A0.9514
C1—C111.557 (3)C113—C1141.365 (5)
C1—C121.561 (3)C114—C1151.374 (5)
C2—C31.505 (4)C115—C1161.387 (5)
C3—C41.461 (5)C121—C1261.388 (4)
C4—C101.491 (4)C121—C1221.392 (4)
C5—C61.376 (3)C122—C1231.392 (4)
C5—C101.389 (3)C123—C1241.365 (6)
C6—C71.380 (4)C124—C1251.366 (7)
C7—C81.372 (3)C125—C1261.383 (5)
C8—C91.390 (3)C61—H61A0.9511
C9—C101.397 (3)C61—H61B0.9507
C11—C1111.515 (3)C61—H61C0.9464
C12—C1211.510 (4)C112—H1120.9523
C3—H3B0.9510C113—H1130.9502
C3—H3A0.9469C114—H1140.9518
C4—H4A0.9494C115—H1150.9490
C4—H4B0.9494C116—H1160.9511
C5—H50.9492C122—H1220.9531
C7—H70.9496C123—H1230.9555
C8—H80.9512C124—H1240.9571
C11—H11A0.9470C125—H1250.9536
C111—C1121.392 (3)C126—H1260.9524
O21···C1113.388 (3)H3A···H11Bviii2.5795
O21···C1163.323 (4)H4A···C61i2.9946
O21···C1213.407 (3)H4A···H61Ci2.5985
O61···C113i3.250 (4)H4B···H52.4166
O21···H11A2.6145H4B···C111viii2.9716
O21···H1162.8768H4B···C112viii2.8556
O21···H126ii2.8519H5···H4B2.4166
O21···H12A2.7037H7···C612.5172
C2···C1163.354 (4)H7···H61A2.3897
C2···C1263.384 (4)H7···H61B2.2215
C3···C1213.463 (4)H7···C121vii2.8830
C8···C1223.590 (4)H7···C122vii2.9787
C8···C1123.553 (4)H8···C112.9716
C9···C1123.150 (3)H8···C122.8335
C9···C1223.225 (4)H8···H11B2.4246
C10···C1123.434 (4)H8···H12B2.2347
C7···H61B2.6846H8···C122vii2.9708
C7···H61A2.8057H11A···O212.6145
C8···H11B2.7718H11A···H12A2.3536
C8···H1222.8650H11A···H1162.3649
C8···H12B2.7061H11A···H126ii2.4383
C8···H1122.8683H11B···C82.7718
C9···H1122.7980H11B···H82.4246
C9···H1222.7694H11B···H1122.5616
C9···H3A3.0669H11B···H3Av2.5795
C11···H82.9716H12A···O212.7037
C111···O213.388 (3)H12A···H11A2.3536
C12···H82.8335H12A···H1262.3037
C112···C93.150 (3)H12B···C82.7061
C112···C83.553 (4)H12B···H82.2347
C112···C103.434 (4)H61A···C72.8057
C113···O61i3.250 (4)H61A···H72.3897
C116···C23.354 (4)H61B···C72.6846
C116···O213.323 (4)H61B···H72.2215
C121···C33.463 (4)H61B···H124iii2.3793
C121···O213.407 (3)H61C···H4Ai2.5985
C122···C93.225 (4)H112···C82.8683
C122···C83.590 (4)H112···C92.7980
C126···C23.384 (4)H112···H11B2.5616
C61···H4Ai2.9946H112···H115vi2.5315
C61···H124iii3.0169H115···C112ix2.9818
C61···H72.5172H115···C113ix3.0283
C61···H116iv3.0456H115···H112ix2.5315
C111···H4Bv2.9716H116···O212.8768
C112···H115vi2.9818H116···C61x3.0456
C112···H4Bv2.8556H116···H11A2.3649
C113···H115vi3.0283H122···C82.8650
C121···H7vii2.8830H122···C92.7694
C121···H3A3.0112H124···C61xi3.0169
C122···H7vii2.9787H124···H61Bxi2.3793
C122···H8vii2.9708H126···H12A2.3037
H3A···C93.0669H126···O21ii2.8519
H3A···C1213.0112H126···H11Aii2.4383
C6—O61—C61118.4 (2)C11—C111—C112121.9 (2)
C2—C1—C9113.67 (19)C1—C11—H11A108.11
C2—C1—C11107.99 (19)C1—C11—H11B108.03
C2—C1—C12105.32 (19)C1—C12—H12A107.81
C9—C1—C11109.40 (18)C1—C12—H12B108.13
C9—C1—C12111.63 (18)C121—C12—H12A108.08
C11—C1—C12108.62 (19)C111—C112—C113120.7 (2)
O21—C2—C1120.7 (2)C121—C12—H12B108.26
O21—C2—C3121.6 (2)H12A—C12—H12B109.61
C1—C2—C3117.5 (2)C112—C113—C114120.8 (3)
C2—C3—C4113.3 (3)C113—C114—C115119.4 (3)
C3—C4—C10113.4 (3)C114—C115—C116120.2 (3)
C6—C5—C10122.3 (2)C111—C116—C115120.9 (3)
O61—C6—C5117.0 (2)C122—C121—C126118.1 (3)
O61—C6—C7123.9 (2)C12—C121—C126119.4 (2)
C5—C6—C7119.1 (2)C12—C121—C122122.5 (2)
C6—C7—C8118.8 (2)C121—C122—C123120.5 (3)
C7—C8—C9123.4 (2)C122—C123—C124120.2 (3)
C1—C9—C8120.0 (2)C123—C124—C125120.0 (3)
C1—C9—C10122.6 (2)C124—C125—C126120.6 (4)
C8—C9—C10117.3 (2)C121—C126—C125120.6 (3)
C4—C10—C5121.0 (2)O61—C61—H61A109.38
C4—C10—C9119.8 (2)O61—C61—H61B109.35
C5—C10—C9119.1 (2)O61—C61—H61C109.53
C1—C11—C111114.1 (2)H61A—C61—H61B109.25
C1—C12—C121114.9 (2)H61A—C61—H61C109.57
C4—C3—H3A108.54H61B—C61—H61C109.73
C2—C3—H3A108.80C111—C112—H112119.71
C2—C3—H3B108.39C113—C112—H112119.57
C4—C3—H3B108.19C112—C113—H113119.73
H3A—C3—H3B109.62C114—C113—H113119.44
C3—C4—H4B108.44C113—C114—H114120.20
C3—C4—H4A108.57C115—C114—H114120.36
H4A—C4—H4B109.54C114—C115—H115119.42
C10—C4—H4A108.37C116—C115—H115120.38
C10—C4—H4B108.51C111—C116—H116119.74
C6—C5—H5118.77C115—C116—H116119.32
C10—C5—H5118.97C121—C122—H122120.00
C8—C7—H7120.79C123—C122—H122119.54
C6—C7—H7120.38C122—C123—H123120.23
C9—C8—H8118.46C124—C123—H123119.55
C7—C8—H8118.14C123—C124—H124119.84
C11—C111—C116120.2 (2)C125—C124—H124120.16
C112—C111—C116117.9 (2)C124—C125—H125119.69
C111—C11—H11A108.40C126—C125—H125119.75
C111—C11—H11B108.40C121—C126—H126119.57
H11A—C11—H11B109.81C125—C126—H126119.80
C61—O61—C6—C5176.9 (3)C8—C9—C10—C50.9 (3)
C61—O61—C6—C73.2 (4)C1—C11—C111—C116100.2 (3)
C9—C1—C2—O21173.0 (2)C1—C11—C111—C11278.1 (3)
C9—C1—C2—C312.1 (3)C1—C12—C121—C12270.8 (3)
C11—C1—C2—O2151.4 (3)C1—C12—C121—C126108.9 (3)
C2—C1—C9—C8174.4 (2)C11—C111—C112—H1122.49
C2—C1—C9—C109.1 (3)C116—C111—C112—H112179.17
C11—C1—C9—C864.8 (3)C11—C111—C116—H1161.67
C11—C1—C9—C10111.7 (2)C112—C111—C116—H116179.96
C11—C1—C2—C3133.7 (2)C111—C112—C113—H113179.88
C12—C1—C2—O2164.5 (3)H112—C112—C113—C114179.31
C12—C1—C2—C3110.4 (3)H112—C112—C113—H1130.45
C9—C1—C11—C11163.5 (2)C112—C113—C114—H114179.33
C12—C1—C11—C111174.38 (18)H113—C113—C114—C115179.59
C2—C1—C12—C12154.4 (2)H113—C113—C114—H1140.90
C9—C1—C12—C12169.4 (2)C113—C114—C115—H115179.04
C11—C1—C12—C121169.85 (19)H114—C114—C115—C116178.96
C12—C1—C9—C855.4 (3)H114—C114—C115—H1151.45
C12—C1—C9—C10128.1 (2)C114—C115—C116—H116179.52
C2—C1—C11—C11160.6 (2)H115—C115—C116—C111179.18
O21—C2—C3—C4142.3 (3)H115—C115—C116—H1160.91
C1—C2—C3—C442.8 (4)C12—C121—C122—H1221.25
C2—C3—C4—C1051.9 (4)C126—C121—C122—H122179.00
C3—C4—C10—C5151.4 (3)C12—C121—C126—H1260.68
C3—C4—C10—C931.9 (4)C122—C121—C126—H126179.56
C10—C5—C6—O61179.6 (2)C121—C122—C123—H123179.96
C10—C5—C6—C70.3 (4)H122—C122—C123—C124179.38
C6—C5—C10—C90.5 (4)H122—C122—C123—H1230.50
C6—C5—C10—C4176.2 (3)C122—C123—C124—H124179.57
O61—C6—C7—C8179.2 (2)H123—C123—C124—C125179.34
C5—C6—C7—C80.8 (4)H123—C123—C124—H1240.55
C6—C7—C8—C90.4 (4)C123—C124—C125—H125179.35
C7—C8—C9—C1177.1 (2)H124—C124—C125—C126179.26
C7—C8—C9—C100.4 (4)H124—C124—C125—H1250.55
C1—C9—C10—C40.7 (4)C124—C125—C126—H126179.74
C1—C9—C10—C5177.5 (2)H125—C125—C126—C121179.74
C8—C9—C10—C4175.9 (2)H125—C125—C126—H1260.06
Symmetry codes: (i) x+2, y+1, z; (ii) x+2, y, z+1; (iii) x+5/2, y+1/2, z+1; (iv) x, y+1, z; (v) x1/2, y+1/2, z; (vi) x+3/2, y+1/2, z; (vii) x+2, y+1, z+1; (viii) x+1/2, y+1/2, z; (ix) x+3/2, y1/2, z; (x) x, y1, z; (xi) x+5/2, y1/2, z+1.
 

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