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In the title compound, C20H22O3, the hexyl­oxy­phenyl group is orthogonal to the isobenzofuran-1-one ring system. The mol­ecules, translated by one unit cell along the a-axis direction, are linked into a chain by inter­molecular C—H...O hydrogen-bonding inter­actions, and the inversion-related mol­ecules of adjacent chains are linked via C—H...O hydrogen bonds to form a ribbon structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806013298/sj2042sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806013298/sj2042Isup2.hkl
Contains datablock I

CCDC reference: 608500

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.058
  • wR factor = 0.187
  • Data-to-parameter ratio = 24.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.51 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.05 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

3-(4-Hexyloxyphenyl)isobenzofuran-1(3H)-one top
Crystal data top
C20H22O3Z = 2
Mr = 310.38F(000) = 332
Triclinic, P1Dx = 1.171 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.1212 (4) ÅCell parameters from 2450 reflections
b = 7.7822 (5) Åθ = 2.9–21.2°
c = 19.9815 (11) ŵ = 0.08 mm1
α = 83.225 (4)°T = 297 K
β = 83.736 (3)°Plate, colourless
γ = 69.062 (3)°0.27 × 0.17 × 0.12 mm
V = 880.48 (10) Å3
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
5086 independent reflections
Radiation source: fine-focus sealed tube2476 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
Detector resolution: 8.33 pixels mm-1θmax = 30.0°, θmin = 1.0°
ω scansh = 88
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1010
Tmin = 0.974, Tmax = 0.991l = 2727
19069 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.187H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0889P)2]
where P = (Fo2 + 2Fc2)/3
5086 reflections(Δ/σ)max = 0.001
208 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.18 e Å3
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
O10.2149 (2)0.79199 (16)0.11917 (6)0.0600 (4)
O20.0525 (2)0.73208 (19)0.06751 (7)0.0728 (4)
O30.5703 (3)0.6832 (2)0.41284 (6)0.0800 (5)
C10.1414 (3)0.6797 (3)0.08677 (9)0.0544 (4)
C20.4598 (3)0.7016 (2)0.13461 (8)0.0501 (4)
H20.55500.76620.10760.060*
C30.5226 (3)0.5121 (2)0.11070 (8)0.0483 (4)
C40.7294 (3)0.3636 (3)0.11361 (9)0.0609 (5)
H40.85770.37010.13280.073*
C50.7396 (4)0.2054 (3)0.08712 (10)0.0731 (6)
H50.87730.10320.08850.088*
C60.5497 (4)0.1948 (3)0.05847 (10)0.0718 (6)
H60.56180.08580.04110.086*
C70.3427 (4)0.3434 (3)0.05524 (9)0.0635 (5)
H70.21470.33760.03570.076*
C80.3337 (3)0.5024 (2)0.08246 (8)0.0505 (4)
C90.4862 (3)0.7043 (2)0.20832 (8)0.0518 (4)
C100.6327 (4)0.7834 (3)0.22873 (9)0.0624 (5)
H100.71100.84060.19630.075*
C110.6670 (4)0.7803 (3)0.29634 (9)0.0668 (5)
H110.76730.83470.30900.080*
C120.5509 (4)0.6958 (3)0.34490 (9)0.0623 (5)
C130.4030 (4)0.6167 (3)0.32496 (9)0.0726 (6)
H130.32310.56070.35740.087*
C140.3719 (4)0.6194 (3)0.25784 (9)0.0675 (6)
H140.27290.56370.24530.081*
C150.7209 (4)0.7616 (3)0.43674 (9)0.0688 (6)
H15A0.66760.89350.42430.083*
H15B0.87930.70680.41680.083*
C160.7169 (4)0.7243 (3)0.51239 (9)0.0701 (6)
H16A0.77040.59200.52390.084*
H16B0.55670.77630.53140.084*
C170.8693 (4)0.8049 (3)0.54360 (10)0.0755 (6)
H17A1.02870.75380.52390.091*
H17B0.81470.93720.53200.091*
C180.8718 (4)0.7691 (3)0.61946 (10)0.0765 (6)
H18A0.71160.81600.63900.092*
H18B0.93160.63670.63090.092*
C191.0153 (5)0.8538 (3)0.65122 (12)0.0944 (8)
H19A0.95560.98630.64010.113*
H19B1.17580.80680.63200.113*
C201.0143 (6)0.8157 (4)0.72690 (12)0.1218 (11)
H20A1.10910.87350.74400.183*
H20B1.07670.68480.73840.183*
H20C0.85650.86450.74650.183*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0521 (8)0.0562 (7)0.0683 (8)0.0103 (6)0.0118 (6)0.0125 (6)
O20.0469 (8)0.0894 (10)0.0801 (9)0.0172 (7)0.0122 (7)0.0141 (7)
O30.0984 (12)0.1104 (12)0.0513 (8)0.0604 (10)0.0038 (7)0.0101 (7)
C10.0465 (11)0.0657 (11)0.0526 (10)0.0203 (9)0.0047 (8)0.0084 (8)
C20.0448 (10)0.0539 (10)0.0531 (10)0.0176 (8)0.0081 (8)0.0046 (8)
C30.0468 (10)0.0516 (10)0.0439 (9)0.0146 (8)0.0039 (7)0.0017 (7)
C40.0561 (12)0.0641 (12)0.0560 (10)0.0126 (10)0.0097 (9)0.0018 (9)
C50.0811 (16)0.0557 (12)0.0665 (12)0.0044 (11)0.0086 (11)0.0025 (9)
C60.0944 (18)0.0540 (12)0.0670 (12)0.0254 (12)0.0024 (12)0.0102 (9)
C70.0714 (14)0.0687 (13)0.0578 (11)0.0320 (11)0.0051 (9)0.0096 (9)
C80.0495 (10)0.0547 (10)0.0481 (9)0.0188 (9)0.0043 (8)0.0046 (7)
C90.0515 (10)0.0550 (10)0.0516 (10)0.0208 (8)0.0048 (8)0.0076 (8)
C100.0709 (13)0.0725 (13)0.0548 (10)0.0390 (11)0.0018 (9)0.0056 (9)
C110.0746 (14)0.0843 (14)0.0581 (11)0.0461 (12)0.0053 (10)0.0118 (9)
C120.0706 (13)0.0746 (12)0.0484 (10)0.0332 (11)0.0014 (9)0.0088 (9)
C130.0827 (15)0.0973 (15)0.0576 (11)0.0580 (13)0.0040 (10)0.0065 (10)
C140.0725 (14)0.0876 (14)0.0611 (11)0.0494 (12)0.0031 (10)0.0118 (10)
C150.0765 (15)0.0794 (13)0.0589 (11)0.0348 (12)0.0089 (10)0.0107 (10)
C160.0803 (15)0.0763 (13)0.0572 (11)0.0300 (12)0.0069 (10)0.0085 (10)
C170.0862 (16)0.0808 (14)0.0653 (12)0.0332 (12)0.0136 (11)0.0089 (10)
C180.0936 (17)0.0766 (14)0.0662 (13)0.0343 (13)0.0200 (12)0.0060 (10)
C190.122 (2)0.0904 (17)0.0830 (15)0.0440 (16)0.0368 (15)0.0046 (12)
C200.176 (3)0.114 (2)0.0848 (18)0.050 (2)0.0543 (19)0.0101 (15)
Geometric parameters (Å, º) top
O1—C11.365 (2)C11—H110.93
O1—C21.461 (2)C12—C131.376 (3)
O2—C11.200 (2)C13—C141.372 (2)
O3—C121.365 (2)C13—H130.93
O3—C151.420 (2)C14—H140.93
C1—C81.464 (3)C15—C161.504 (2)
C2—C91.503 (2)C15—H15A0.97
C2—C31.507 (2)C15—H15B0.97
C2—H20.98C16—C171.513 (3)
C3—C81.370 (2)C16—H16A0.97
C3—C41.377 (3)C16—H16B0.97
C4—C51.376 (3)C17—C181.509 (3)
C4—H40.93C17—H17A0.97
C5—C61.382 (3)C17—H17B0.97
C5—H50.93C18—C191.497 (3)
C6—C71.378 (3)C18—H18A0.97
C6—H60.93C18—H18B0.97
C7—C81.390 (2)C19—C201.506 (3)
C7—H70.93C19—H19A0.97
C9—C101.372 (2)C19—H19B0.97
C9—C141.389 (2)C20—H20A0.96
C10—C111.386 (2)C20—H20B0.96
C10—H100.93C20—H20C0.96
C11—C121.383 (3)
C1—O1—C2110.96 (13)C14—C13—H13119.6
C12—O3—C15118.57 (15)C12—C13—H13119.6
O2—C1—O1120.99 (17)C13—C14—C9120.94 (17)
O2—C1—C8130.87 (17)C13—C14—H14119.5
O1—C1—C8108.14 (15)C9—C14—H14119.5
O1—C2—C9110.75 (14)O3—C15—C16108.14 (16)
O1—C2—C3103.14 (13)O3—C15—H15A110.1
C9—C2—C3115.05 (14)C16—C15—H15A110.1
O1—C2—H2109.2O3—C15—H15B110.1
C9—C2—H2109.2C16—C15—H15B110.1
C3—C2—H2109.2H15A—C15—H15B108.4
C8—C3—C4121.14 (16)C15—C16—C17112.72 (17)
C8—C3—C2109.07 (15)C15—C16—H16A109.0
C4—C3—C2129.79 (16)C17—C16—H16A109.0
C5—C4—C3117.64 (19)C15—C16—H16B109.0
C5—C4—H4121.2C17—C16—H16B109.0
C3—C4—H4121.2H16A—C16—H16B107.8
C4—C5—C6121.5 (2)C18—C17—C16114.39 (17)
C4—C5—H5119.3C18—C17—H17A108.7
C6—C5—H5119.3C16—C17—H17A108.7
C7—C6—C5121.01 (19)C18—C17—H17B108.7
C7—C6—H6119.5C16—C17—H17B108.7
C5—C6—H6119.5H17A—C17—H17B107.6
C6—C7—C8117.10 (19)C19—C18—C17114.91 (19)
C6—C7—H7121.5C19—C18—H18A108.5
C8—C7—H7121.5C17—C18—H18A108.5
C3—C8—C7121.62 (17)C19—C18—H18B108.5
C3—C8—C1108.57 (15)C17—C18—H18B108.5
C7—C8—C1129.80 (17)H18A—C18—H18B107.5
C10—C9—C14117.84 (16)C18—C19—C20113.7 (2)
C10—C9—C2120.94 (16)C18—C19—H19A108.8
C14—C9—C2121.15 (16)C20—C19—H19A108.8
C9—C10—C11121.78 (17)C18—C19—H19B108.8
C9—C10—H10119.1C20—C19—H19B108.8
C11—C10—H10119.1H19A—C19—H19B107.7
C12—C11—C10119.52 (18)C19—C20—H20A109.5
C12—C11—H11120.2C19—C20—H20B109.5
C10—C11—H11120.2H20A—C20—H20B109.5
O3—C12—C13115.75 (17)C19—C20—H20C109.5
O3—C12—C11125.10 (17)H20A—C20—H20C109.5
C13—C12—C11119.14 (17)H20B—C20—H20C109.5
C14—C13—C12120.77 (18)
C2—O1—C1—O2177.10 (16)O1—C1—C8—C7178.73 (16)
C2—O1—C1—C83.16 (18)O1—C2—C9—C10122.40 (18)
C1—O1—C2—C9126.92 (15)C3—C2—C9—C10121.15 (19)
C1—O1—C2—C33.32 (17)O1—C2—C9—C1460.6 (2)
O1—C2—C3—C82.24 (17)C3—C2—C9—C1455.8 (2)
C9—C2—C3—C8122.95 (16)C14—C9—C10—C110.1 (3)
O1—C2—C3—C4178.23 (16)C2—C9—C10—C11177.21 (17)
C9—C2—C3—C457.5 (2)C9—C10—C11—C120.1 (3)
C8—C3—C4—C50.0 (3)C15—O3—C12—C13179.79 (18)
C2—C3—C4—C5179.44 (16)C15—O3—C12—C110.2 (3)
C3—C4—C5—C60.1 (3)C10—C11—C12—O3179.8 (2)
C4—C5—C6—C70.2 (3)C10—C11—C12—C130.2 (3)
C5—C6—C7—C80.5 (3)O3—C12—C13—C14179.35 (19)
C4—C3—C8—C70.4 (3)C11—C12—C13—C140.7 (3)
C2—C3—C8—C7179.18 (15)C12—C13—C14—C90.9 (3)
C4—C3—C8—C1179.93 (15)C10—C9—C14—C130.6 (3)
C2—C3—C8—C10.49 (19)C2—C9—C14—C13177.70 (19)
C6—C7—C8—C30.6 (3)C12—O3—C15—C16178.27 (17)
C6—C7—C8—C1179.79 (17)O3—C15—C16—C17179.08 (17)
O2—C1—C8—C3178.67 (19)C15—C16—C17—C18179.50 (18)
O1—C1—C8—C31.63 (19)C16—C17—C18—C19178.0 (2)
O2—C1—C8—C71.0 (3)C17—C18—C19—C20180.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O2i0.982.383.213 (2)143
C7—H7···O2ii0.932.573.399 (3)148
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z.
 

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