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The mol­ecule of the title compound, C22H22O2, possesses a crystallographically imposed twofold axis. The two terminal phen­yl rings both make a dihedral angle of 82.5 (2)° with the central benzene ring. The crystal packing is stabilized mainly by van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805018076/cv6522sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805018076/cv6522Isup2.hkl
Contains datablock I

CCDC reference: 272419

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.045
  • wR factor = 0.120
  • Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELX97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

1,2-Dimethyl-4,5-bis(phenoxymethyl)benzene top
Crystal data top
C22H22O2F(000) = 680
Mr = 318.40Dx = 1.177 Mg m3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 1978 reflections
a = 18.476 (4) Åθ = 2.4–21.6°
b = 11.494 (2) ŵ = 0.07 mm1
c = 8.4632 (17) ÅT = 292 K
V = 1797.2 (6) Å3Block, colourless
Z = 40.25 × 0.20 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1180 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.057
Graphite monochromatorθmax = 27.0°, θmin = 2.1°
φ and ω scansh = 1523
11066 measured reflectionsk = 1414
1964 independent reflectionsl = 1010
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.120 w = 1/[σ2(Fo2) + (0.065P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.89(Δ/σ)max < 0.001
1964 reflectionsΔρmax = 0.16 e Å3
111 parametersΔρmin = 0.14 e Å3
0 restraintsExtinction correction: SHELX97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0048 (13)
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
xyzUiso*/Ueq
C10.43465 (10)0.16487 (16)0.1444 (2)0.0868 (6)
H1A0.39360.18350.07970.130*
H1B0.41910.11970.23360.130*
H1C0.46900.12090.08370.130*
C20.46968 (8)0.27578 (12)0.20161 (16)0.0556 (4)
C30.44101 (7)0.38191 (12)0.15413 (16)0.0545 (4)
H30.40070.38190.08830.065*
C40.46975 (7)0.48726 (12)0.20034 (15)0.0485 (4)
C50.43709 (8)0.59838 (12)0.14030 (16)0.0586 (4)
H5A0.47410.65800.13200.070*
H5B0.41640.58610.03630.070*
C60.34705 (7)0.73729 (12)0.21541 (16)0.0502 (4)
C70.28919 (8)0.76423 (14)0.31232 (18)0.0638 (5)
H70.27580.71390.39320.077*
C80.25153 (9)0.86597 (15)0.2883 (2)0.0750 (5)
H80.21250.88390.35350.090*
C90.27045 (10)0.94099 (15)0.1706 (2)0.0749 (5)
H90.24481.00980.15600.090*
C100.32745 (9)0.91424 (14)0.0741 (2)0.0701 (5)
H100.34040.96520.00650.084*
C110.36603 (8)0.81240 (13)0.09492 (19)0.0593 (4)
H110.40450.79460.02830.071*
O10.38194 (5)0.63455 (8)0.24871 (11)0.0592 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0962 (13)0.0684 (12)0.0956 (13)0.0207 (10)0.0014 (11)0.0113 (9)
C20.0555 (9)0.0555 (9)0.0557 (9)0.0077 (7)0.0084 (7)0.0041 (7)
C30.0432 (8)0.0668 (11)0.0535 (8)0.0017 (7)0.0010 (7)0.0018 (7)
C40.0440 (8)0.0540 (9)0.0474 (8)0.0030 (6)0.0069 (6)0.0018 (6)
C50.0539 (9)0.0649 (10)0.0570 (9)0.0111 (7)0.0103 (7)0.0055 (7)
C60.0441 (8)0.0504 (9)0.0562 (8)0.0007 (6)0.0029 (7)0.0027 (7)
C70.0533 (10)0.0725 (11)0.0657 (10)0.0059 (8)0.0069 (8)0.0039 (8)
C80.0601 (11)0.0828 (13)0.0820 (13)0.0157 (10)0.0026 (9)0.0198 (11)
C90.0728 (12)0.0585 (11)0.0935 (14)0.0161 (9)0.0158 (10)0.0171 (10)
C100.0740 (11)0.0536 (10)0.0826 (12)0.0011 (8)0.0096 (9)0.0020 (8)
C110.0556 (9)0.0561 (10)0.0663 (10)0.0019 (7)0.0022 (7)0.0009 (8)
O10.0539 (6)0.0615 (7)0.0622 (6)0.0106 (5)0.0146 (5)0.0093 (5)
Geometric parameters (Å, º) top
C1—C21.509 (2)C6—O11.3746 (16)
C1—H1A0.9600C6—C111.381 (2)
C1—H1B0.9600C6—C71.382 (2)
C1—H1C0.9600C7—C81.376 (2)
C2—C2i1.388 (3)C7—H70.9300
C2—C31.3892 (19)C8—C91.364 (2)
C3—C41.3787 (18)C8—H80.9300
C3—H30.9300C9—C101.368 (2)
C4—C4i1.399 (3)C9—H90.9300
C4—C51.5011 (18)C10—C111.382 (2)
C5—O11.4329 (16)C10—H100.9300
C5—H5A0.9700C11—H110.9300
C5—H5B0.9700
C2—C1—H1A109.5H5A—C5—H5B108.4
C2—C1—H1B109.5O1—C6—C11124.69 (13)
H1A—C1—H1B109.5O1—C6—C7115.68 (13)
C2—C1—H1C109.5C11—C6—C7119.63 (14)
H1A—C1—H1C109.5C8—C7—C6119.59 (16)
H1B—C1—H1C109.5C8—C7—H7120.2
C2i—C2—C3118.58 (9)C6—C7—H7120.2
C2i—C2—C1122.37 (10)C9—C8—C7121.04 (16)
C3—C2—C1119.04 (15)C9—C8—H8119.5
C4—C3—C2122.84 (14)C7—C8—H8119.5
C4—C3—H3118.6C8—C9—C10119.46 (16)
C2—C3—H3118.6C8—C9—H9120.3
C3—C4—C4i118.57 (8)C10—C9—H9120.3
C3—C4—C5119.76 (13)C9—C10—C11120.76 (16)
C4i—C4—C5121.65 (8)C9—C10—H10119.6
O1—C5—C4108.42 (11)C11—C10—H10119.6
O1—C5—H5A110.0C6—C11—C10119.52 (15)
C4—C5—H5A110.0C6—C11—H11120.2
O1—C5—H5B110.0C10—C11—H11120.2
C4—C5—H5B110.0C6—O1—C5116.84 (10)
C2i—C2—C3—C40.7 (3)C7—C8—C9—C100.5 (3)
C1—C2—C3—C4179.79 (14)C8—C9—C10—C110.2 (2)
C2—C3—C4—C4i0.2 (2)O1—C6—C11—C10179.12 (13)
C2—C3—C4—C5178.21 (12)C7—C6—C11—C100.8 (2)
C3—C4—C5—O190.40 (15)C9—C10—C11—C60.5 (2)
C4i—C4—C5—O191.26 (18)C11—C6—O1—C56.5 (2)
O1—C6—C7—C8179.44 (13)C7—C6—O1—C5173.60 (12)
C11—C6—C7—C80.5 (2)C4—C5—O1—C6178.23 (11)
C6—C7—C8—C90.2 (2)
Symmetry code: (i) x+1, y, z+1/2.
 

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