Literature DB >> 21588415

4-Decyl-phenyl 4-benz-yloxy-3-methyl-benzoate.

H K Arun Kashi, B S Palakshamurthy, M Vinduvahini, H T Srinivasa, H C Devarajegowda.   

Abstract

In the title compound, C(31)H(38)O(3), the central benzene ring makes dihedral angles of 66.06 (9) and 65.21 (8)°, respectively, with the benzyl and 4-decyl-phenyl rings.

Entities:  

Year:  2010        PMID: 21588415      PMCID: PMC3007531          DOI: 10.1107/S1600536810028965

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


Related literature

For general background to benzyl­oxybenzoate, see: Laschat (2009 ▶); Meter & Klanderman (1973 ▶); Young et al. (1974 ▶); Tinn et al. (1982 ▶). For the synthesis, see: Sadashiva & Subba (1975 ▶); Sadashiva (1979 ▶); Hari et al. (2009 ▶). For related structures, see: Blake et al. (1996 ▶); Chin & Goodby (1986 ▶).

Experimental

Crystal data

C31H38O3 M = 458.61 Triclinic, a = 9.3684 (16) Å b = 11.168 (2) Å c = 15.204 (3) Å α = 68.588 (11)° β = 87.274 (11)° γ = 65.578 (10)° V = 1338.3 (4) Å3 Z = 2 Mo Kα radiation μ = 0.07 mm−1 T = 295 K 0.22 × 0.15 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: ψ scan (SADABS; Sheldrick, 2004 ▶) T min = 0.987, T max = 0.992 23986 measured reflections 6737 independent reflections 3840 reflections with I > 2σ(I) R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.053 wR(F 2) = 0.183 S = 1.04 6737 reflections 308 parameters 6 restraints H-atom parameters constrained Δρmax = 0.37 e Å−3 Δρmin = −0.28 e Å−3 Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810028965/gw2084sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028965/gw2084Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C31H38O3Z = 2
Mr = 458.61F(000) = 496
Triclinic, P1Dx = 1.138 Mg m3
Hall symbol: -P 1Melting point: 339 K
a = 9.3684 (16) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.168 (2) ÅCell parameters from 6737 reflections
c = 15.204 (3) Åθ = 1.5–28.5°
α = 68.588 (11)°µ = 0.07 mm1
β = 87.274 (11)°T = 295 K
γ = 65.578 (10)°Plate, colourless
V = 1338.3 (4) Å30.22 × 0.15 × 0.12 mm
Bruker SMART CCD area-detector diffractometer6737 independent reflections
Radiation source: fine-focus sealed tube3840 reflections with I > 2σ(I)
graphiteRint = 0.034
ω and φ scansθmax = 28.5°, θmin = 1.5°
Absorption correction: ψ scan (SADABS; Sheldrick, 2004)h = −12→12
Tmin = 0.987, Tmax = 0.992k = −14→14
23986 measured reflectionsl = −19→20
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.183w = 1/[σ2(Fo2) + (0.0834P)2 + 0.1711P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
6737 reflectionsΔρmax = 0.37 e Å3
308 parametersΔρmin = −0.28 e Å3
6 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.009 (2)
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 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*/Ueq
O11.29391 (13)0.71764 (13)0.39798 (8)0.0596 (3)
O20.76009 (16)0.85364 (16)0.66658 (10)0.0782 (4)
O30.66987 (13)0.76081 (12)0.58579 (8)0.0587 (3)
C11.7436 (2)0.6890 (3)0.21401 (16)0.0773 (6)
H11.81610.67250.17100.093*
C21.7328 (2)0.5776 (2)0.28609 (18)0.0808 (6)
H21.79870.48490.29260.097*
C31.6246 (2)0.6016 (2)0.34940 (15)0.0734 (5)
H31.61780.52490.39830.088*
C41.52641 (19)0.73813 (19)0.34098 (13)0.0563 (4)
C51.5386 (2)0.85005 (19)0.26763 (14)0.0654 (5)
H51.47280.94310.26050.078*
C61.6476 (2)0.8246 (2)0.20518 (15)0.0770 (6)
H61.65600.90060.15650.092*
C81.16997 (18)0.74083 (16)0.45050 (11)0.0493 (4)
C71.4092 (2)0.7663 (2)0.40939 (14)0.0703 (5)
H7A1.46190.71630.47410.084*
H7B1.35820.86720.39670.084*
C91.05899 (18)0.69493 (15)0.43409 (11)0.0478 (4)
C100.93050 (18)0.71552 (16)0.48486 (11)0.0490 (4)
H100.85520.68640.47460.059*
C110.91080 (18)0.77889 (16)0.55122 (11)0.0493 (4)
C121.0225 (2)0.82287 (19)0.56523 (12)0.0578 (4)
H121.01020.86570.60900.069*
C131.1519 (2)0.80452 (19)0.51555 (12)0.0589 (4)
H131.22620.83470.52570.071*
C141.0830 (2)0.6250 (2)0.36370 (14)0.0680 (5)
H14A1.17840.62080.33620.102*
H14B0.99500.67890.31440.102*
H14C1.09080.53040.39550.102*
C150.77674 (19)0.80247 (17)0.60752 (12)0.0538 (4)
C160.53999 (18)0.77559 (18)0.63921 (11)0.0512 (4)
C170.5292 (2)0.65529 (18)0.70043 (13)0.0611 (5)
H170.60600.56600.70670.073*
C180.4030 (2)0.66829 (18)0.75268 (13)0.0604 (4)
H180.39580.58640.79430.072*
C190.28666 (19)0.79952 (17)0.74503 (11)0.0501 (4)
C200.30000 (19)0.91846 (17)0.68052 (12)0.0561 (4)
H200.22251.00820.67270.067*
C210.42535 (19)0.90750 (18)0.62747 (12)0.0553 (4)
H210.43180.98880.58430.066*
C220.1539 (2)0.80822 (18)0.80631 (13)0.0608 (4)
H22A0.08960.77110.78650.073*
H22B0.19970.74620.87160.073*
C230.0474 (2)0.95323 (19)0.80478 (13)0.0612 (5)
H23A−0.00871.01300.74130.073*
H23B0.11160.99520.81840.073*
C24−0.0723 (2)0.9519 (2)0.87570 (13)0.0650 (5)
H24A−0.13990.91430.86010.078*
H24B−0.01640.88830.93880.078*
C25−0.1748 (2)1.0969 (2)0.87793 (13)0.0634 (5)
H25A−0.23471.15940.81570.076*
H25B−0.10731.13650.89080.076*
C26−0.2886 (2)1.0926 (2)0.95230 (13)0.0632 (5)
H26A−0.35081.04680.94190.076*
H26B−0.22801.03471.01470.076*
C27−0.4000 (2)1.23739 (19)0.95192 (13)0.0639 (5)
H27A−0.33831.28170.96540.077*
H27B−0.45781.29700.88890.077*
C28−0.5169 (2)1.23037 (19)1.02399 (13)0.0641 (5)
H28A−0.57451.18191.01190.077*
H28B−0.45821.17311.08700.077*
C29−0.6347 (2)1.3720 (2)1.02406 (14)0.0687 (5)
H29A−0.57811.41931.03890.082*
H29B−0.69171.43100.96070.082*
C30−0.7516 (2)1.3592 (2)1.09440 (16)0.0803 (6)
H30A−0.69391.29391.15670.096*
H30B−0.81331.31831.07640.096*
C31−0.8634 (3)1.4982 (3)1.1015 (2)0.1154 (9)
H31A−0.93381.48141.14750.173*
H31B−0.92351.56291.04060.173*
H31C−0.80391.53861.12100.173*
U11U22U33U12U13U23
O10.0546 (7)0.0750 (8)0.0666 (7)−0.0390 (6)0.0209 (6)−0.0339 (6)
O20.0796 (9)0.1107 (11)0.0799 (9)−0.0556 (8)0.0335 (7)−0.0593 (9)
O30.0524 (7)0.0696 (7)0.0669 (7)−0.0305 (6)0.0233 (6)−0.0365 (6)
C10.0557 (11)0.0991 (17)0.0911 (15)−0.0335 (11)0.0254 (10)−0.0522 (14)
C20.0535 (11)0.0668 (13)0.1176 (18)−0.0144 (10)0.0078 (12)−0.0426 (13)
C30.0661 (12)0.0579 (11)0.0869 (14)−0.0293 (10)0.0077 (11)−0.0141 (10)
C40.0497 (9)0.0661 (11)0.0632 (10)−0.0336 (8)0.0118 (8)−0.0257 (9)
C50.0630 (11)0.0566 (10)0.0798 (12)−0.0285 (9)0.0197 (10)−0.0272 (10)
C60.0774 (13)0.0784 (14)0.0781 (13)−0.0423 (11)0.0282 (11)−0.0246 (11)
C80.0475 (8)0.0491 (9)0.0492 (9)−0.0228 (7)0.0098 (7)−0.0143 (7)
C70.0669 (11)0.0982 (15)0.0767 (12)−0.0548 (11)0.0256 (10)−0.0456 (11)
C90.0482 (8)0.0435 (8)0.0505 (9)−0.0206 (7)0.0084 (7)−0.0156 (7)
C100.0464 (8)0.0461 (8)0.0543 (9)−0.0219 (7)0.0086 (7)−0.0167 (7)
C110.0470 (8)0.0468 (9)0.0483 (9)−0.0183 (7)0.0071 (7)−0.0138 (7)
C120.0614 (10)0.0672 (11)0.0534 (9)−0.0313 (9)0.0119 (8)−0.0283 (8)
C130.0579 (10)0.0720 (11)0.0612 (10)−0.0376 (9)0.0123 (8)−0.0297 (9)
C140.0688 (11)0.0793 (12)0.0822 (13)−0.0439 (10)0.0274 (10)−0.0466 (11)
C150.0533 (9)0.0544 (10)0.0533 (9)−0.0239 (8)0.0114 (8)−0.0193 (8)
C160.0487 (9)0.0589 (10)0.0524 (9)−0.0245 (8)0.0147 (7)−0.0272 (8)
C170.0562 (10)0.0496 (10)0.0747 (12)−0.0189 (8)0.0180 (9)−0.0260 (9)
C180.0635 (11)0.0488 (9)0.0668 (11)−0.0254 (8)0.0186 (9)−0.0191 (8)
C190.0526 (9)0.0529 (9)0.0463 (8)−0.0235 (8)0.0113 (7)−0.0200 (7)
C200.0555 (10)0.0482 (9)0.0569 (10)−0.0177 (8)0.0141 (8)−0.0176 (8)
C210.0565 (10)0.0521 (9)0.0539 (9)−0.0239 (8)0.0157 (8)−0.0165 (8)
C220.0629 (10)0.0609 (10)0.0570 (10)−0.0274 (9)0.0208 (8)−0.0212 (8)
C230.0589 (10)0.0642 (11)0.0607 (10)−0.0265 (9)0.0209 (8)−0.0252 (9)
C240.0634 (11)0.0686 (12)0.0645 (11)−0.0301 (9)0.0266 (9)−0.0268 (9)
C250.0613 (10)0.0698 (12)0.0623 (10)−0.0303 (9)0.0229 (9)−0.0275 (9)
C260.0605 (10)0.0658 (11)0.0616 (10)−0.0261 (9)0.0214 (9)−0.0249 (9)
C270.0634 (11)0.0632 (11)0.0679 (11)−0.0285 (9)0.0213 (9)−0.0275 (9)
C280.0654 (11)0.0616 (11)0.0658 (11)−0.0271 (9)0.0217 (9)−0.0261 (9)
C290.0682 (12)0.0637 (11)0.0731 (12)−0.0270 (9)0.0228 (10)−0.0279 (10)
C300.0715 (12)0.0821 (14)0.0890 (14)−0.0307 (11)0.0319 (11)−0.0393 (12)
C310.0906 (17)0.108 (2)0.138 (2)−0.0207 (15)0.0451 (16)−0.0656 (18)
O1—C81.3664 (18)C18—C191.384 (2)
O1—C71.436 (2)C18—H180.9300
O2—C151.2021 (19)C19—C201.384 (2)
O3—C151.363 (2)C19—C221.510 (2)
O3—C161.4161 (18)C20—C211.381 (2)
C1—C61.362 (3)C20—H200.9300
C1—C21.363 (3)C21—H210.9300
C1—H10.9300C22—C231.502 (2)
C2—C31.377 (3)C22—H22A0.9700
C2—H20.9300C22—H22B0.9700
C3—C41.377 (3)C23—C241.519 (2)
C3—H30.9300C23—H23A0.9700
C4—C51.381 (2)C23—H23B0.9700
C4—C71.494 (2)C24—C251.515 (2)
C5—C61.375 (3)C24—H24A0.9700
C5—H50.9300C24—H24B0.9700
C6—H60.9300C25—C261.518 (2)
C8—C131.382 (2)C25—H25A0.9700
C8—C91.402 (2)C25—H25B0.9700
C7—H7A0.9700C26—C271.517 (2)
C7—H7B0.9700C26—H26A0.9700
C9—C101.382 (2)C26—H26B0.9700
C9—C141.500 (2)C27—C281.517 (2)
C10—C111.396 (2)C27—H27A0.9700
C10—H100.9300C27—H27B0.9700
C11—C121.380 (2)C28—C291.509 (2)
C11—C151.472 (2)C28—H28A0.9700
C12—C131.380 (2)C28—H28B0.9700
C12—H120.9300C29—C301.507 (2)
C13—H130.9300C29—H29A0.9700
C14—H14A0.9600C29—H29B0.9700
C14—H14B0.9600C30—C311.512 (3)
C14—H14C0.9600C30—H30A0.9700
C16—C171.368 (2)C30—H30B0.9700
C16—C211.369 (2)C31—H31A0.9600
C17—C181.380 (2)C31—H31B0.9600
C17—H170.9300C31—H31C0.9600
C8—O1—C7117.75 (13)C21—C20—H20119.1
C15—O3—C16116.52 (12)C19—C20—H20119.1
C6—C1—C2119.72 (19)C16—C21—C20119.21 (15)
C6—C1—H1120.1C16—C21—H21120.4
C2—C1—H1120.1C20—C21—H21120.4
C1—C2—C3120.29 (19)C23—C22—C19116.47 (14)
C1—C2—H2119.9C23—C22—H22A108.2
C3—C2—H2119.9C19—C22—H22A108.2
C2—C3—C4120.56 (18)C23—C22—H22B108.2
C2—C3—H3119.7C19—C22—H22B108.2
C4—C3—H3119.7H22A—C22—H22B107.3
C3—C4—C5118.56 (16)C22—C23—C24113.59 (14)
C3—C4—C7121.33 (17)C22—C23—H23A108.8
C5—C4—C7120.12 (17)C24—C23—H23A108.8
C6—C5—C4120.29 (17)C22—C23—H23B108.8
C6—C5—H5119.9C24—C23—H23B108.8
C4—C5—H5119.9H23A—C23—H23B107.7
C1—C6—C5120.58 (19)C25—C24—C23113.85 (15)
C1—C6—H6119.7C25—C24—H24A108.8
C5—C6—H6119.7C23—C24—H24A108.8
O1—C8—C13123.80 (14)C25—C24—H24B108.8
O1—C8—C9115.06 (14)C23—C24—H24B108.8
C13—C8—C9121.13 (14)H24A—C24—H24B107.7
O1—C7—C4108.23 (14)C24—C25—C26113.16 (15)
O1—C7—H7A110.1C24—C25—H25A108.9
C4—C7—H7A110.1C26—C25—H25A108.9
O1—C7—H7B110.1C24—C25—H25B108.9
C4—C7—H7B110.1C26—C25—H25B108.9
H7A—C7—H7B108.4H25A—C25—H25B107.8
C10—C9—C8117.95 (14)C27—C26—C25114.33 (15)
C10—C9—C14122.26 (14)C27—C26—H26A108.7
C8—C9—C14119.78 (14)C25—C26—H26A108.7
C9—C10—C11121.69 (15)C27—C26—H26B108.7
C9—C10—H10119.2C25—C26—H26B108.7
C11—C10—H10119.2H26A—C26—H26B107.6
C12—C11—C10118.62 (14)C28—C27—C26113.14 (15)
C12—C11—C15117.55 (14)C28—C27—H27A109.0
C10—C11—C15123.83 (15)C26—C27—H27A109.0
C13—C12—C11121.27 (15)C28—C27—H27B109.0
C13—C12—H12119.4C26—C27—H27B109.0
C11—C12—H12119.4H27A—C27—H27B107.8
C12—C13—C8119.34 (16)C29—C28—C27115.36 (16)
C12—C13—H13120.3C29—C28—H28A108.4
C8—C13—H13120.3C27—C28—H28A108.4
C9—C14—H14A109.5C29—C28—H28B108.4
C9—C14—H14B109.5C27—C28—H28B108.4
H14A—C14—H14B109.5H28A—C28—H28B107.5
C9—C14—H14C109.5C30—C29—C28113.17 (16)
H14A—C14—H14C109.5C30—C29—H29A108.9
H14B—C14—H14C109.5C28—C29—H29A108.9
O2—C15—O3122.27 (15)C30—C29—H29B108.9
O2—C15—C11124.65 (16)C28—C29—H29B108.9
O3—C15—C11113.08 (14)H29A—C29—H29B107.8
C17—C16—C21120.86 (14)C29—C30—C31114.4 (2)
C17—C16—O3118.55 (14)C29—C30—H30A108.7
C21—C16—O3120.56 (14)C31—C30—H30A108.7
C16—C17—C18119.10 (15)C29—C30—H30B108.7
C16—C17—H17120.5C31—C30—H30B108.7
C18—C17—H17120.5H30A—C30—H30B107.6
C17—C18—C19121.97 (16)C30—C31—H31A109.5
C17—C18—H18119.0C30—C31—H31B109.5
C19—C18—H18119.0H31A—C31—H31B109.5
C18—C19—C20117.03 (14)C30—C31—H31C109.5
C18—C19—C22119.99 (15)H31A—C31—H31C109.5
C20—C19—C22122.97 (14)H31B—C31—H31C109.5
C21—C20—C19121.78 (15)
C6—C1—C2—C30.5 (3)C16—O3—C15—C11177.94 (13)
C1—C2—C3—C4−0.2 (3)C12—C11—C15—O2−2.2 (3)
C2—C3—C4—C50.2 (3)C10—C11—C15—O2178.07 (17)
C2—C3—C4—C7−179.54 (17)C12—C11—C15—O3177.47 (14)
C3—C4—C5—C6−0.5 (3)C10—C11—C15—O3−2.3 (2)
C7—C4—C5—C6179.25 (17)C15—O3—C16—C17−112.35 (17)
C2—C1—C6—C5−0.8 (3)C15—O3—C16—C2169.6 (2)
C4—C5—C6—C10.8 (3)C21—C16—C17—C18−1.8 (3)
C7—O1—C8—C13−1.9 (2)O3—C16—C17—C18−179.82 (15)
C7—O1—C8—C9178.12 (15)C16—C17—C18—C190.0 (3)
C8—O1—C7—C4−176.37 (14)C17—C18—C19—C201.6 (3)
C3—C4—C7—O1−65.5 (2)C17—C18—C19—C22−177.81 (16)
C5—C4—C7—O1114.78 (18)C18—C19—C20—C21−1.4 (2)
O1—C8—C9—C10−179.88 (13)C22—C19—C20—C21177.94 (16)
C13—C8—C9—C100.1 (2)C17—C16—C21—C202.0 (3)
O1—C8—C9—C140.6 (2)O3—C16—C21—C20179.92 (14)
C13—C8—C9—C14−179.41 (16)C19—C20—C21—C16−0.3 (3)
C8—C9—C10—C11−0.5 (2)C18—C19—C22—C23170.77 (16)
C14—C9—C10—C11179.02 (16)C20—C19—C22—C23−8.6 (3)
C9—C10—C11—C120.6 (2)C19—C22—C23—C24−173.87 (15)
C9—C10—C11—C15−179.63 (14)C22—C23—C24—C25177.16 (16)
C10—C11—C12—C13−0.4 (3)C23—C24—C25—C26−177.39 (15)
C15—C11—C12—C13179.87 (15)C24—C25—C26—C27−176.29 (16)
C11—C12—C13—C80.0 (3)C25—C26—C27—C28177.49 (16)
O1—C8—C13—C12−179.87 (15)C26—C27—C28—C29−177.76 (16)
C9—C8—C13—C120.1 (3)C27—C28—C29—C30177.89 (17)
C16—O3—C15—O2−2.4 (2)C28—C29—C30—C31175.6 (2)
D—H···AD—HH···AD···AD—H···A
C10—H10···O30.932.472.786 (2)100
C14—H14A···O10.962.242.726 (3)110
  2 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.  Progress in liquid crystal chemistry.

Authors:  Sabine Laschat
Journal:  Beilstein J Org Chem       Date:  2009-10-07       Impact factor: 2.883

  2 in total
  2 in total

1.  Crystal structure and Hirshfeld surface analysis of 3-({4-[(4-cyano-phen-oxy)carbon-yl]phen-oxy}carbon-yl)phenyl 4-(benz-yloxy)-3-chloro-benzoate.

Authors:  S Selvanandan; H Anil Kumar; H T Srinivasa; B S Palakshamurthy
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2022-09-08

2.  Methyl 4-benz-yloxy-2-hy-droxy-benzoate.

Authors:  B S Palakshamurthy; H T Srinivasa; Vijith Kumar; S Sreenivasa; H C Devarajegowda
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-11-17
  2 in total

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