Literature DB >> 22969559

4-[5-(4-Formyl-phen-oxy)pent-oxy]benzaldehyde.

Tomislav Balić1, Berislav Marković, Ivana Balić.   

Abstract

In the title compound, C(20)H(19)O(4), the benzene rings, linked via five methyl-ene C atoms, form a dihedral angle of 77.28 (6)°. In the crystal, mol-ecules are linked via pairs of weak C-H⋯O inter-actions [graph set R(2) (2)(6)] into dimers that are further connected by additional weak C-H⋯O interactions [graph sets R(2) (2)(14), R(2) (2)(26) and R(2) (2)(6)].

Entities:  

Year:  2012        PMID： 22969559      PMCID： PMC3435688          DOI： 10.1107/S1600536812034241

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


Related literature

For related structures and the synthesis of similar compounds, see: Ali et al. (2010 ▶); Dehno Khalaji et al. (2011 ▶); Han & Zhen (2005 ▶); Narasimha Moorthy et al. (2005 ▶). For the synthesis of Schiff bases and Schiff base complexes, see: Ma & Cao (2011 ▶); Ilhan et al. (2007 ▶); Keypour et al. (2008 ▶). For graph-set analysis, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C19H20O4 M = 312.35 Monoclinic, a = 22.3018 (8) Å b = 4.6829 (16) Å c = 31.6082 (12) Å β = 103.752 (4)° V = 3206.5 (11) Å3 Z = 8 Mo Kα radiation μ = 0.09 mm−1 T = 190 K 0.51 × 0.37 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.975, T max = 1.000 9589 measured reflections 3136 independent reflections 2560 reflections with I > 2σ(I) R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.039 wR(F 2) = 0.098 S = 1.06 3136 reflections 208 parameters H-atom parameters constrained Δρmax = 0.19 e Å−3 Δρmin = −0.18 e Å−3 Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶), PARST97 (Nardelli, 1995 ▶) and Mercury (Macrae et al., 2006 ▶). Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812034241/nc2286sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034241/nc2286Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812034241/nc2286Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C19H20O4F(000) = 1328
Mr = 312.35Dx = 1.294 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4466 reflections
a = 22.3018 (8) Åθ = 4.3–28.4°
b = 4.6829 (16) ŵ = 0.09 mm−1
c = 31.6082 (12) ÅT = 190 K
β = 103.752 (4)°Block, colourless
V = 3206.5 (11) Å30.51 × 0.37 × 0.18 mm
Z = 8
Oxford Diffraction Xcalibur Sapphire3 diffractometer3136 independent reflections
Radiation source: Enhance (Mo) X-ray Source2560 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
ω scansθmax = 26.0°, θmin = 4.3°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)h = −24→27
Tmin = 0.975, Tmax = 1.000k = −5→5
9589 measured reflectionsl = −38→37
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0389P)2 + 1.7845P] where P = (Fo2 + 2Fc2)/3
3136 reflections(Δ/σ)max = 0.001
208 parametersΔρmax = 0.19 e Å−3
0 restraintsΔρmin = −0.18 e Å−3
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.
xyzUiso*/Ueq
O10.08040 (5)1.1018 (3)0.38389 (4)0.0547 (3)
O20.18750 (4)0.2636 (2)0.54219 (3)0.0319 (2)
O30.32553 (4)0.2744 (2)0.72116 (3)0.0285 (2)
O40.42945 (5)1.1213 (2)0.87886 (3)0.0477 (3)
C10.06143 (7)1.0219 (3)0.41477 (5)0.0405 (4)
H10.02261.09310.41730.049*
C20.09356 (6)0.8247 (3)0.44835 (4)0.0304 (3)
C30.06566 (6)0.7310 (3)0.48055 (5)0.0338 (3)
H30.02540.79720.48060.041*
C40.09498 (6)0.5429 (3)0.51280 (4)0.0312 (3)
H40.07520.48150.53470.037*
C50.15385 (6)0.4457 (3)0.51250 (4)0.0268 (3)
C60.18249 (6)0.5389 (3)0.48024 (4)0.0330 (3)
H60.22270.47230.48000.040*
C70.15283 (6)0.7264 (3)0.44882 (4)0.0341 (3)
H70.17280.79010.42720.041*
C80.16073 (6)0.1576 (3)0.57633 (4)0.0299 (3)
H8A0.12260.04860.56370.036*
H8B0.15000.31850.59340.036*
C90.20774 (6)−0.0332 (3)0.60517 (4)0.0298 (3)
H9A0.2207−0.18200.58690.036*
H9B0.1880−0.13060.62620.036*
C100.26483 (6)0.1251 (3)0.63036 (4)0.0283 (3)
H10A0.25170.28990.64560.034*
H10B0.28780.20040.60950.034*
C110.30789 (6)−0.0631 (3)0.66370 (4)0.0301 (3)
H11A0.2830−0.17200.68030.036*
H11B0.3282−0.20250.64810.036*
C120.35692 (6)0.1019 (3)0.69529 (4)0.0285 (3)
H12A0.3861−0.03050.71410.034*
H12B0.38030.22460.67940.034*
C130.35974 (6)0.4398 (3)0.75307 (4)0.0247 (3)
C140.32629 (6)0.6109 (3)0.77544 (4)0.0280 (3)
H140.28250.60470.76800.034*
C150.35664 (6)0.7880 (3)0.80814 (4)0.0300 (3)
H150.33360.90490.82310.036*
C160.42127 (6)0.7984 (3)0.81970 (4)0.0301 (3)
C170.45393 (6)0.6280 (3)0.79728 (4)0.0320 (3)
H170.49780.63410.80480.038*
C180.42406 (6)0.4486 (3)0.76408 (4)0.0296 (3)
H180.44710.33300.74900.036*
C190.45393 (7)0.9823 (3)0.85514 (5)0.0378 (4)
H190.49760.99400.86000.045*
U11U22U33U12U13U23
O10.0500 (7)0.0681 (8)0.0458 (7)0.0129 (6)0.0108 (5)0.0243 (6)
O20.0310 (5)0.0398 (6)0.0251 (5)0.0092 (4)0.0069 (4)0.0049 (4)
O30.0253 (5)0.0331 (5)0.0267 (5)−0.0014 (4)0.0056 (4)−0.0033 (4)
O40.0512 (6)0.0523 (7)0.0426 (6)−0.0169 (6)0.0171 (5)−0.0155 (5)
C10.0343 (8)0.0446 (9)0.0405 (8)0.0074 (7)0.0045 (7)0.0073 (7)
C20.0290 (7)0.0312 (7)0.0286 (7)0.0024 (6)0.0024 (5)−0.0014 (6)
C30.0246 (7)0.0385 (8)0.0370 (8)0.0056 (6)0.0045 (6)−0.0006 (6)
C40.0275 (7)0.0363 (8)0.0303 (7)0.0016 (6)0.0080 (6)0.0005 (6)
C50.0279 (6)0.0285 (7)0.0219 (6)0.0029 (6)0.0016 (5)−0.0030 (5)
C60.0284 (7)0.0407 (8)0.0305 (7)0.0088 (6)0.0080 (6)0.0011 (6)
C70.0335 (7)0.0411 (8)0.0285 (7)0.0047 (6)0.0090 (6)0.0030 (6)
C80.0301 (7)0.0325 (7)0.0270 (7)−0.0021 (6)0.0065 (6)−0.0006 (6)
C90.0334 (7)0.0266 (7)0.0278 (7)−0.0009 (6)0.0042 (6)0.0005 (5)
C100.0331 (7)0.0256 (7)0.0251 (7)−0.0005 (6)0.0048 (6)0.0008 (5)
C110.0362 (7)0.0268 (7)0.0255 (7)0.0010 (6)0.0035 (6)0.0004 (5)
C120.0294 (7)0.0298 (7)0.0267 (7)0.0035 (6)0.0074 (5)0.0015 (6)
C130.0262 (6)0.0257 (7)0.0216 (6)−0.0024 (5)0.0043 (5)0.0043 (5)
C140.0241 (6)0.0325 (7)0.0277 (7)−0.0011 (6)0.0065 (5)0.0031 (6)
C150.0333 (7)0.0303 (7)0.0283 (7)−0.0002 (6)0.0113 (6)0.0006 (6)
C160.0332 (7)0.0299 (7)0.0271 (7)−0.0055 (6)0.0069 (6)0.0023 (6)
C170.0255 (7)0.0356 (8)0.0332 (7)−0.0039 (6)0.0038 (6)0.0013 (6)
C180.0266 (6)0.0319 (7)0.0306 (7)0.0003 (6)0.0076 (6)0.0007 (6)
C190.0370 (8)0.0405 (8)0.0360 (8)−0.0114 (7)0.0092 (7)−0.0035 (7)
O1—C11.2118 (18)C9—H9A0.9900
O2—C51.3552 (15)C9—H9B0.9900
O2—C81.4401 (15)C10—C111.5261 (17)
O3—C131.3541 (15)C10—H10A0.9900
O3—C121.4436 (15)C10—H10B0.9900
O4—C191.2160 (18)C11—C121.5069 (18)
C1—C21.4596 (19)C11—H11A0.9900
C1—H10.9500C11—H11B0.9900
C2—C31.3847 (19)C12—H12A0.9900
C2—C71.3963 (19)C12—H12B0.9900
C3—C41.3876 (19)C13—C181.3938 (17)
C3—H30.9500C13—C141.3962 (18)
C4—C51.3915 (18)C14—C151.3717 (18)
C4—H40.9500C14—H140.9500
C5—C61.3957 (19)C15—C161.4009 (18)
C6—C71.3719 (19)C15—H150.9500
C6—H60.9500C16—C171.3838 (19)
C7—H70.9500C16—C191.4626 (19)
C8—C91.5081 (18)C17—C181.3850 (19)
C8—H8A0.9900C17—H170.9500
C8—H8B0.9900C18—H180.9500
C9—C101.5241 (18)C19—H190.9500
C5—O2—C8118.40 (10)C11—C10—H10A109.0
C13—O3—C12118.60 (10)C9—C10—H10B109.0
O1—C1—C2125.17 (14)C11—C10—H10B109.0
O1—C1—H1117.4H10A—C10—H10B107.8
C2—C1—H1117.4C12—C11—C10113.55 (11)
C3—C2—C7118.51 (13)C12—C11—H11A108.9
C3—C2—C1120.40 (12)C10—C11—H11A108.9
C7—C2—C1121.08 (13)C12—C11—H11B108.9
C2—C3—C4121.69 (12)C10—C11—H11B108.9
C2—C3—H3119.2H11A—C11—H11B107.7
C4—C3—H3119.2O3—C12—C11106.81 (10)
C3—C4—C5118.91 (13)O3—C12—H12A110.4
C3—C4—H4120.5C11—C12—H12A110.4
C5—C4—H4120.5O3—C12—H12B110.4
O2—C5—C4124.71 (12)C11—C12—H12B110.4
O2—C5—C6115.36 (11)H12A—C12—H12B108.6
C4—C5—C6119.92 (12)O3—C13—C18124.55 (12)
C7—C6—C5120.23 (12)O3—C13—C14115.54 (11)
C7—C6—H6119.9C18—C13—C14119.91 (12)
C5—C6—H6119.9C15—C14—C13120.08 (12)
C6—C7—C2120.73 (13)C15—C14—H14120.0
C6—C7—H7119.6C13—C14—H14120.0
C2—C7—H7119.6C14—C15—C16120.69 (13)
O2—C8—C9107.74 (10)C14—C15—H15119.7
O2—C8—H8A110.2C16—C15—H15119.7
C9—C8—H8A110.2C17—C16—C15118.72 (12)
O2—C8—H8B110.2C17—C16—C19120.32 (12)
C9—C8—H8B110.2C15—C16—C19120.96 (13)
H8A—C8—H8B108.5C16—C17—C18121.38 (12)
C8—C9—C10113.70 (11)C16—C17—H17119.3
C8—C9—H9A108.8C18—C17—H17119.3
C10—C9—H9A108.8C17—C18—C13119.22 (12)
C8—C9—H9B108.8C17—C18—H18120.4
C10—C9—H9B108.8C13—C18—H18120.4
H9A—C9—H9B107.7O4—C19—C16124.93 (14)
C9—C10—C11112.96 (11)O4—C19—H19117.5
C9—C10—H10A109.0C16—C19—H19117.5
O1—C1—C2—C3−175.26 (16)C9—C10—C11—C12−167.57 (11)
O1—C1—C2—C74.8 (2)C13—O3—C12—C11178.44 (10)
C7—C2—C3—C4−0.2 (2)C10—C11—C12—O365.94 (14)
C1—C2—C3—C4179.78 (13)C12—O3—C13—C18−2.50 (17)
C2—C3—C4—C5−0.3 (2)C12—O3—C13—C14177.13 (11)
C8—O2—C5—C40.99 (19)O3—C13—C14—C15−179.49 (11)
C8—O2—C5—C6−179.73 (11)C18—C13—C14—C150.16 (19)
C3—C4—C5—O2179.59 (12)C13—C14—C15—C16−0.43 (19)
C3—C4—C5—C60.3 (2)C14—C15—C16—C170.5 (2)
O2—C5—C6—C7−179.25 (12)C14—C15—C16—C19−178.70 (13)
C4—C5—C6—C70.1 (2)C15—C16—C17—C18−0.2 (2)
C5—C6—C7—C2−0.6 (2)C19—C16—C17—C18178.94 (13)
C3—C2—C7—C60.7 (2)C16—C17—C18—C130.0 (2)
C1—C2—C7—C6−179.35 (14)O3—C13—C18—C17179.69 (12)
C5—O2—C8—C9−178.73 (11)C14—C13—C18—C170.07 (19)
O2—C8—C9—C1066.89 (14)C17—C16—C19—O4−173.80 (14)
C8—C9—C10—C11172.47 (11)C15—C16—C19—O45.4 (2)
D—H···AD—HH···AD···AD—H···A
C1—H1···O4i0.952.533.3401 (18)144
C8—H8B···O4ii0.992.583.4815 (18)152
C6—H6···O2iii0.952.533.4487 (16)163
C12—H12B···O1iv0.992.503.4360 (18)157
C14—H14···O3v0.952.633.4977 (15)151
C19—H19···O1vi0.952.633.3698 (19)135
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C1—H1⋯O4i 0.952.533.3401 (18)144
C8—H8B⋯O4ii 0.992.583.4815 (18)152
C6—H6⋯O2iii 0.952.533.4487 (16)163
C12—H12B⋯O1iv 0.992.503.4360 (18)157
C14—H14⋯O3v 0.952.633.4977 (15)151
C19—H19⋯O1vi 0.952.633.3698 (19)135

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

  4 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.  4,4'-(Propane-1,3-diyldi-oxy)dibenz-aldehyde.

Authors:  Qamar Ali; Muhammad Raza Shah; Seik Weng Ng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-06-09

3.  4-{2-[2-(4-Formyl-phen-oxy)eth-oxy]eth-oxy}benzaldehyde.

Authors:  Zhen Ma; Yiqun Cao
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-05-25

4.  2-[4-(2-Formyl-phen-oxy)-but-oxy]-benzaldehyde.

Authors:  Aliakbar Dehno Khalaji; Salar Hafez Ghoran; Kazuma Gotoh; Hiroyuki Ishida
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-08-27
  4 in total
  1 in total

1.  Triclinic polymorph of 4-[4-(4-formyl-phen-oxy)but-oxy]benzaldehyde.

Authors:  Tomislav Balić; Berislav Marković; Ivana Balić
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-12-22
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.