Literature DB >> 26594556

Crystal structure of 2-(2,3-di-meth-oxy-naphthalen-1-yl)-3-hy-droxy-6-meth-oxy-4H-chromen-4-one.

Seunghyun Ahn1, Yoongho Lim1, Dongsoo Koh2.   

Abstract

In the title compound, C22H18O6, the dimeth-oxy-substituted naphthalene ring system is twisted relative to the 4H-chromenon skeleton by 88.96 (3)°. The two meth-oxy substituents are tilted from the naphthalene ring system by 1.4 (4) and 113.0 (2)°, respectively. An intra-molecular O-H⋯O hydrogen bond closes an S(5) ring motif. In the crystal, pairs of O-H⋯O hydrogen bonds form inversion dimers with R (2) 2(10) loops and C-H⋯O inter-actions connect the dimers into [010] chains.

Entities:  

Keywords:  crystal structure; flavonol; fluorescence; hydrogen bonding

Year:  2015        PMID： 26594556      PMCID： PMC4645031          DOI： 10.1107/S2056989015018861

Source DB:  PubMed          Journal:  Acta Crystallogr E Crystallogr Commun


Related literature

For the synthesis and biological properties of flavonols, see: Burmistrova et al. (2014 ▸); Lee et al. (2014 ▸); Dias et al. (2013 ▸); Yong et al. (2013 ▸); Klymchenko et al. (2003 ▸). For flavonols in natural products, see: Bendaikha et al. (2014 ▸); Prescott et al. (2013 ▸). For related structures, see: Narita et al. (2015 ▸); Yoo et al. (2014 ▸); Serdiuk et al. (2013 ▸).

Experimental

Crystal data

C22H18O6 M = 378.36 Monoclinic, a = 11.8571 (12) Å b = 9.0888 (9) Å c = 17.3977 (17) Å β = 95.253 (2)° V = 1867.0 (3) Å3 Z = 4 Mo Kα radiation μ = 0.10 mm−1 T = 200 K 0.19 × 0.11 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer 13406 measured reflections 4625 independent reflections 2786 reflections with I > 2σ(I) R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.055 wR(F 2) = 0.184 S = 1.11 4625 reflections 257 parameters H-atom parameters constrained Δρmax = 0.28 e Å−3 Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 2000 ▸); cell refinement: SAINT (Bruker, 2000 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: SHELXTL (Sheldrick, 2008 ▸); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015018861/ff2142sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015018861/ff2142Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S2056989015018861/ff2142Isup3.cml Click here for additional data file. . DOI: 10.1107/S2056989015018861/ff2142fig1.tif Mol­ecular structure of the title compound, showing the atom-labelling scheme and with displacement ellipsoids drawn at the 50% probability level. Click here for additional data file. . DOI: 10.1107/S2056989015018861/ff2142fig2.tif Part of the crystal structure with inter­molecular O—H⋯O hydrogen bonds shown as brown dashed lines and C—H⋯O inter­actions shown as blue dashed lines. Click here for additional data file. . DOI: 10.1107/S2056989015018861/ff2142fig3.tif Synthetic scheme for the title compound. CCDC reference: 1430031 Additional supporting information: crystallographic information; 3D view; checkCIF report
C22H18O6F(000) = 792
Mr = 378.36Dx = 1.346 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4844 reflections
a = 11.8571 (12) Åθ = 2.4–28.2°
b = 9.0888 (9) ŵ = 0.10 mm−1
c = 17.3977 (17) ÅT = 200 K
β = 95.253 (2)°Block, yellow
V = 1867.0 (3) Å30.19 × 0.11 × 0.05 mm
Z = 4
Bruker SMART CCD area-detector diffractometer2786 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.036
Graphite monochromatorθmax = 28.3°, θmin = 1.7°
phi and ω scansh = −15→10
13406 measured reflectionsk = −11→12
4625 independent reflectionsl = −22→23
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184H-atom parameters constrained
S = 1.11w = 1/[σ2(Fo2) + (0.0751P)2 + 0.4684P] where P = (Fo2 + 2Fc2)/3
4625 reflections(Δ/σ)max < 0.001
257 parametersΔρmax = 0.28 e Å−3
0 restraintsΔρmin = −0.29 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
C10.19294 (16)0.5697 (2)0.04954 (11)0.0324 (4)
O10.12049 (12)0.59265 (17)−0.00540 (8)0.0419 (4)
C20.16533 (16)0.4835 (2)0.11528 (11)0.0334 (4)
O20.05942 (12)0.42964 (18)0.11735 (9)0.0444 (4)
H20.02020.45190.07630.067*
C30.24396 (16)0.4529 (2)0.17434 (12)0.0346 (5)
O30.35228 (12)0.50146 (17)0.17607 (8)0.0430 (4)
C40.38419 (18)0.5844 (2)0.11559 (13)0.0425 (5)
C50.4958 (2)0.6288 (3)0.11996 (15)0.0592 (7)
H50.54670.60230.16310.071*
C60.5324 (2)0.7113 (3)0.06168 (16)0.0659 (8)
H60.60960.74020.06380.079*
C70.45694 (19)0.7541 (3)−0.00160 (15)0.0533 (7)
C80.34661 (18)0.7105 (3)−0.00567 (13)0.0434 (5)
H80.29580.7393−0.04840.052*
C90.30769 (17)0.6229 (2)0.05332 (12)0.0358 (5)
O40.50460 (14)0.8384 (3)−0.05520 (11)0.0737 (6)
C100.4292 (3)0.8899 (4)−0.11779 (19)0.0901 (12)
H10A0.39530.8057−0.14650.135*
H10B0.47110.9502−0.15220.135*
H10C0.36940.9491−0.09780.135*
C110.22233 (16)0.3626 (2)0.24206 (12)0.0353 (5)
C120.18157 (18)0.4294 (2)0.30418 (12)0.0395 (5)
C130.15722 (19)0.3451 (3)0.36980 (12)0.0437 (5)
C140.16900 (19)0.1962 (3)0.36856 (13)0.0457 (6)
H140.14940.13990.41140.055*
C150.20979 (18)0.1235 (3)0.30471 (13)0.0429 (5)
C160.2199 (2)−0.0312 (3)0.30177 (16)0.0541 (6)
H160.1991−0.08870.34380.065*
C170.2589 (2)−0.0992 (3)0.23987 (17)0.0620 (7)
H170.2643−0.20350.23880.074*
C180.2910 (2)−0.0160 (3)0.17768 (17)0.0600 (7)
H180.3193−0.06410.13490.072*
C190.2818 (2)0.1338 (3)0.17818 (14)0.0480 (6)
H190.30420.18910.13580.058*
C200.23973 (17)0.2073 (2)0.24075 (12)0.0394 (5)
O50.16815 (13)0.57945 (17)0.30440 (9)0.0469 (4)
C210.0524 (2)0.6294 (3)0.30143 (18)0.0666 (8)
H21A0.00140.54430.29720.100*
H21B0.03610.69350.25650.100*
H21C0.04110.68420.34860.100*
O60.12322 (16)0.4267 (2)0.42964 (9)0.0579 (5)
C220.1006 (3)0.3472 (4)0.49711 (16)0.0753 (9)
H22A0.03460.28350.48530.113*
H22B0.08510.41660.53800.113*
H22C0.16650.28690.51450.113*
U11U22U33U12U13U23
C10.0330 (10)0.0339 (10)0.0302 (10)−0.0019 (8)0.0018 (8)−0.0013 (8)
O10.0368 (8)0.0538 (9)0.0339 (8)−0.0092 (7)−0.0029 (6)0.0068 (7)
C20.0314 (10)0.0361 (11)0.0329 (10)−0.0056 (8)0.0047 (8)0.0003 (8)
O20.0315 (8)0.0612 (10)0.0395 (8)−0.0139 (7)−0.0020 (6)0.0109 (7)
C30.0322 (10)0.0345 (10)0.0369 (10)−0.0035 (8)0.0018 (8)0.0025 (8)
O30.0312 (8)0.0541 (10)0.0426 (8)−0.0087 (6)−0.0025 (6)0.0135 (7)
C40.0367 (12)0.0464 (13)0.0439 (12)−0.0070 (9)0.0018 (9)0.0111 (10)
C50.0349 (12)0.0815 (19)0.0585 (15)−0.0148 (12)−0.0095 (11)0.0268 (14)
C60.0351 (13)0.091 (2)0.0703 (18)−0.0192 (13)−0.0024 (12)0.0313 (16)
C70.0389 (13)0.0680 (17)0.0532 (14)−0.0144 (11)0.0047 (10)0.0190 (12)
C80.0355 (12)0.0540 (14)0.0404 (12)−0.0096 (10)0.0017 (9)0.0095 (10)
C90.0333 (11)0.0369 (11)0.0371 (11)−0.0054 (8)0.0024 (8)0.0000 (9)
O40.0433 (10)0.1098 (17)0.0676 (12)−0.0240 (10)0.0024 (8)0.0421 (12)
C100.0637 (19)0.128 (3)0.076 (2)−0.0287 (19)−0.0054 (16)0.059 (2)
C110.0290 (10)0.0396 (11)0.0366 (11)−0.0044 (8)−0.0010 (8)0.0072 (9)
C120.0365 (11)0.0424 (12)0.0388 (11)−0.0050 (9)−0.0014 (9)0.0044 (9)
C130.0448 (13)0.0507 (14)0.0353 (11)−0.0063 (10)0.0018 (9)0.0038 (10)
C140.0436 (13)0.0549 (14)0.0378 (12)−0.0068 (10)0.0001 (9)0.0126 (10)
C150.0370 (12)0.0431 (12)0.0476 (13)−0.0033 (9)−0.0026 (9)0.0113 (10)
C160.0561 (15)0.0451 (14)0.0611 (16)−0.0010 (11)0.0048 (12)0.0147 (12)
C170.0683 (18)0.0414 (14)0.0770 (19)0.0033 (12)0.0113 (15)0.0110 (13)
C180.0646 (17)0.0470 (15)0.0698 (18)0.0048 (12)0.0144 (13)−0.0025 (13)
C190.0478 (13)0.0444 (13)0.0521 (14)0.0010 (10)0.0065 (10)0.0069 (11)
C200.0333 (11)0.0415 (12)0.0425 (12)−0.0022 (9)−0.0014 (9)0.0061 (10)
O50.0501 (10)0.0394 (9)0.0511 (9)−0.0035 (7)0.0040 (7)0.0007 (7)
C210.0572 (17)0.0562 (16)0.088 (2)0.0128 (13)0.0158 (14)0.0053 (15)
O60.0759 (12)0.0630 (12)0.0363 (9)−0.0054 (9)0.0126 (8)0.0012 (8)
C220.099 (2)0.087 (2)0.0412 (14)0.0023 (18)0.0173 (14)0.0098 (15)
C1—O11.243 (2)C12—O51.373 (3)
C1—C91.440 (3)C12—C131.426 (3)
C1—C21.448 (3)C13—C141.361 (3)
C2—O21.351 (2)C13—O61.369 (3)
C2—C31.352 (3)C14—C151.415 (3)
O2—H20.8400C14—H140.9500
C3—O31.356 (2)C15—C161.413 (3)
C3—C111.477 (3)C15—C201.420 (3)
O3—C41.375 (2)C16—C171.359 (4)
C4—C51.379 (3)C16—H160.9500
C4—C91.392 (3)C17—C181.401 (4)
C5—C61.363 (3)C17—H170.9500
C5—H50.9500C18—C191.366 (3)
C6—C71.409 (3)C18—H180.9500
C6—H60.9500C19—C201.407 (3)
C7—C81.362 (3)C19—H190.9500
C7—O41.368 (3)O5—C211.442 (3)
C8—C91.410 (3)C21—H21A0.9800
C8—H80.9500C21—H21B0.9800
O4—C101.423 (3)C21—H21C0.9800
C10—H10A0.9800O6—C221.425 (3)
C10—H10B0.9800C22—H22A0.9800
C10—H10C0.9800C22—H22B0.9800
C11—C121.366 (3)C22—H22C0.9800
C11—C201.427 (3)
O1—C1—C9124.23 (18)C11—C12—C13120.4 (2)
O1—C1—C2120.52 (18)O5—C12—C13120.0 (2)
C9—C1—C2115.25 (16)C14—C13—O6126.1 (2)
O2—C2—C3118.88 (18)C14—C13—C12119.5 (2)
O2—C2—C1119.66 (16)O6—C13—C12114.4 (2)
C3—C2—C1121.45 (18)C13—C14—C15121.3 (2)
C2—O2—H2109.5C13—C14—H14119.3
C2—C3—O3122.40 (18)C15—C14—H14119.3
C2—C3—C11124.24 (18)C16—C15—C14122.0 (2)
O3—C3—C11113.35 (16)C16—C15—C20118.5 (2)
C3—O3—C4119.20 (15)C14—C15—C20119.5 (2)
O3—C4—C5116.63 (19)C17—C16—C15121.2 (2)
O3—C4—C9121.86 (18)C17—C16—H16119.4
C5—C4—C9121.5 (2)C15—C16—H16119.4
C6—C5—C4119.3 (2)C16—C17—C18120.2 (2)
C6—C5—H5120.4C16—C17—H17119.9
C4—C5—H5120.4C18—C17—H17119.9
C5—C6—C7120.7 (2)C19—C18—C17120.4 (3)
C5—C6—H6119.7C19—C18—H18119.8
C7—C6—H6119.7C17—C18—H18119.8
C8—C7—O4125.6 (2)C18—C19—C20120.8 (2)
C8—C7—C6119.9 (2)C18—C19—H19119.6
O4—C7—C6114.5 (2)C20—C19—H19119.6
C7—C8—C9120.2 (2)C19—C20—C15118.9 (2)
C7—C8—H8119.9C19—C20—C11122.9 (2)
C9—C8—H8119.9C15—C20—C11118.1 (2)
C4—C9—C8118.37 (18)C12—O5—C21115.00 (18)
C4—C9—C1119.78 (19)O5—C21—H21A109.5
C8—C9—C1121.83 (18)O5—C21—H21B109.5
C7—O4—C10115.85 (19)H21A—C21—H21B109.5
O4—C10—H10A109.5O5—C21—H21C109.5
O4—C10—H10B109.5H21A—C21—H21C109.5
H10A—C10—H10B109.5H21B—C21—H21C109.5
O4—C10—H10C109.5C13—O6—C22116.3 (2)
H10A—C10—H10C109.5O6—C22—H22A109.5
H10B—C10—H10C109.5O6—C22—H22B109.5
C12—C11—C20120.96 (19)H22A—C22—H22B109.5
C12—C11—C3118.94 (19)O6—C22—H22C109.5
C20—C11—C3120.05 (19)H22A—C22—H22C109.5
C11—C12—O5119.55 (19)H22B—C22—H22C109.5
O1—C1—C2—O2−1.1 (3)C2—C3—C11—C2090.0 (3)
C9—C1—C2—O2179.49 (18)O3—C3—C11—C20−89.0 (2)
O1—C1—C2—C3177.6 (2)C20—C11—C12—O5178.55 (17)
C9—C1—C2—C3−1.8 (3)C3—C11—C12—O5−4.0 (3)
O2—C2—C3—O3179.25 (18)C20—C11—C12—C131.0 (3)
C1—C2—C3—O30.6 (3)C3—C11—C12—C13178.53 (18)
O2—C2—C3—C110.3 (3)C11—C12—C13—C14−3.6 (3)
C1—C2—C3—C11−178.38 (19)O5—C12—C13—C14178.93 (19)
C2—C3—O3—C4−0.3 (3)C11—C12—C13—O6176.38 (19)
C11—C3—O3—C4178.71 (19)O5—C12—C13—O6−1.1 (3)
C3—O3—C4—C5−179.0 (2)O6—C13—C14—C15−177.1 (2)
C3—O3—C4—C91.5 (3)C12—C13—C14—C152.8 (3)
O3—C4—C5—C6180.0 (3)C13—C14—C15—C16−178.5 (2)
C9—C4—C5—C6−0.6 (4)C13—C14—C15—C200.4 (3)
C4—C5—C6—C71.5 (5)C14—C15—C16—C17179.8 (2)
C5—C6—C7—C8−1.3 (5)C20—C15—C16—C170.9 (4)
C5—C6—C7—O4179.1 (3)C15—C16—C17—C180.7 (4)
O4—C7—C8—C9179.7 (3)C16—C17—C18—C19−1.0 (4)
C6—C7—C8—C90.1 (4)C17—C18—C19—C20−0.2 (4)
O3—C4—C9—C8178.8 (2)C18—C19—C20—C151.8 (3)
C5—C4—C9—C8−0.6 (4)C18—C19—C20—C11−176.3 (2)
O3—C4—C9—C1−2.9 (3)C16—C15—C20—C19−2.1 (3)
C5—C4—C9—C1177.7 (2)C14—C15—C20—C19179.0 (2)
C7—C8—C9—C40.8 (4)C16—C15—C20—C11176.02 (19)
C7—C8—C9—C1−177.4 (2)C14—C15—C20—C11−2.8 (3)
O1—C1—C9—C4−176.5 (2)C12—C11—C20—C19−179.8 (2)
C2—C1—C9—C42.9 (3)C3—C11—C20—C192.7 (3)
O1—C1—C9—C81.7 (3)C12—C11—C20—C152.1 (3)
C2—C1—C9—C8−178.8 (2)C3—C11—C20—C15−175.34 (18)
C8—C7—O4—C103.5 (5)C11—C12—O5—C21113.0 (2)
C6—C7—O4—C10−176.8 (3)C13—C12—O5—C21−69.5 (3)
C2—C3—C11—C12−87.5 (3)C14—C13—O6—C221.4 (3)
O3—C3—C11—C1293.5 (2)C12—C13—O6—C22−178.6 (2)
D—H···AD—HH···AD···AD—H···A
O2—H2···O10.842.322.750 (2)112
O2—H2···O1i0.842.022.7613 (19)146
C14—H14···O1ii0.952.603.502 (3)158
C17—H17···O5iii0.952.603.342 (3)136
C22—H22A···O1iv0.982.583.509 (4)159
Table 1

Hydrogen-bond geometry (, )

DHA DHHA D A DHA
O2H2O10.842.322.750(2)112
O2H2O1i 0.842.022.761(2)146
C14H14O1ii 0.952.603.502(3)158
C17H17O5iii 0.952.603.342(3)136
C22H22AO1iv 0.982.583.509(4)159

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

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  1 in total

1.  Chrysin Inhibits NF-κB-Dependent CCL5 Transcription by Targeting IκB Kinase in the Atopic Dermatitis-Like Inflammatory Microenvironment.

Authors:  Hyunjin Yeo; Young Han Lee; Dongsoo Koh; Yoongho Lim; Soon Young Shin
Journal:  Int J Mol Sci       Date:  2020-10-05       Impact factor: 5.923
  1 in total

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