Literature DB >> 26396807

Crystal structure of 4-oxo-4H-chromene-3-carb-oxy-lic acid.

Yoshinobu Ishikawa1.   

Abstract

In the title compound, C10H6O4, also known as 3-carb-oxy-chromone, the non-H atoms of the chromone ring are essentially coplanar (r.m.s. deviation = 0.0057 Å), with the maximum deviation from their least-squares plane [0.011 (2) Å] being for a pyran C atom. The dihedral angle between the fused ring and plane of the carb-oxy group is 3.06 (2)°. An intra-molecular hydrogen bond is formed between the ring carbonyl O atom and the carb-oxy O-H atom, closing an S(6) loop. In the crystal, mol-ecules are assembled by stacking inter-actions [centroid-centroid distance between the benzene and pyran rings = 3.844 (3) Å] and C-H⋯O hydrogen bonds, generating a three-dimensional network. Short contacts are also observed between the carb-oxy O and C atoms [C=O⋯C=O = 3.002 (3) Å].

Entities:  

Keywords:  chromone; crystal structure; hydrogen bonding; stacking inter­action

Year:  2015        PMID： 26396807      PMCID： PMC4571407          DOI： 10.1107/S2056989015013456

Source DB:  PubMed          Journal:  Acta Crystallogr E Crystallogr Commun


Related literature

For the biological activities of the title compound and its related compounds, see: Alcaro et al. (2010 ▸); Gaspar et al. (2012 ▸); Legoabe et al. (2012 ▸); Papaneophytou et al. (2015 ▸). For the synthesis of the title compound, see: Helguera et al. (2013 ▸).

Experimental

Crystal data

C10H6O4 M = 190.15 Monoclinic, a = 18.017 (8) Å b = 5.549 (3) Å c = 8.017 (5) Å β = 92.49 (4)° V = 800.8 (8) Å3 Z = 4 Mo Kα radiation μ = 0.12 mm−1 T = 100 K 0.37 × 0.35 × 0.05 mm

Data collection

Rigaku AFC-7R diffractometer 2228 measured reflections 1831 independent reflections 1183 reflections with F 2 > 2.0σ(F 2) R int = 0.098 3 standard reflections every 150 reflections intensity decay: −1.6%

Refinement

R[F 2 > 2σ(F 2)] = 0.047 wR(F 2) = 0.124 S = 1.04 1831 reflections 128 parameters H-atom parameters constrained Δρmax = 0.24 e Å−3 Δρmin = −0.24 e Å−3

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999 ▸); cell refinement: WinAFC Diffractometer Control Software; data reduction: WinAFC Diffractometer Control Software; program(s) used to solve structure: CrystalStructure (Rigaku, 2010 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: CrystalStructure (Rigaku, 2010 ▸); software used to prepare material for publication: CrystalStructure. Crystal structure: contains datablock(s) General, I. DOI: 10.1107/S2056989015013456/tk5375sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015013456/tk5375Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S2056989015013456/tk5375Isup3.cml Click here for additional data file. . DOI: 10.1107/S2056989015013456/tk5375fig1.tif The mol­ecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are shown as small spheres of arbitrary radius. Click here for additional data file. . DOI: 10.1107/S2056989015013456/tk5375fig2.tif A view of the inter­molecular inter­actions of the title compound. Intra­molecular O—H⋯O and inter­molecular C—H⋯O hydrogen bonds are represented as dashed lines. CCDC reference: 1412580 Additional supporting information: crystallographic information; 3D view; checkCIF report
C10H6O4F(000) = 392.00
Mr = 190.15Dx = 1.577 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 18.017 (8) Åθ = 15.0–17.3°
b = 5.549 (3) ŵ = 0.12 mm−1
c = 8.017 (5) ÅT = 100 K
β = 92.49 (4)°Plate, colourless
V = 800.8 (8) Å30.37 × 0.35 × 0.05 mm
Z = 4
Rigaku AFC-7R diffractometerθmax = 27.5°
ω–2θ scansh = −23→23
2228 measured reflectionsk = 0→7
1831 independent reflectionsl = −10→5
1183 reflections with F2 > 2.0σ(F2)3 standard reflections every 150 reflections
Rint = 0.098 intensity decay: −1.6%
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0605P)2 + 0.0457P] where P = (Fo2 + 2Fc2)/3
1831 reflections(Δ/σ)max < 0.001
128 parametersΔρmax = 0.24 e Å−3
0 restraintsΔρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methods
Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).
xyzUiso*/Ueq
O10.05120 (7)1.2950 (3)0.66885 (17)0.0166 (4)
O20.09613 (7)0.6952 (3)0.95238 (17)0.0190 (4)
O30.22945 (8)0.8524 (3)1.00156 (19)0.0230 (4)
O40.26339 (8)1.1851 (3)0.87416 (19)0.0233 (4)
C10.11926 (10)1.2529 (4)0.7381 (3)0.0165 (5)
C20.13725 (10)1.0587 (4)0.8324 (3)0.0147 (4)
C30.08209 (10)0.8780 (4)0.8660 (3)0.0145 (4)
C4−0.05085 (10)0.7609 (4)0.8086 (3)0.0158 (4)
C5−0.11971 (11)0.8094 (4)0.7329 (3)0.0184 (5)
C6−0.13077 (11)1.0194 (4)0.6379 (3)0.0192 (5)
C7−0.07373 (11)1.1805 (4)0.6183 (3)0.0167 (4)
C80.00821 (10)0.9221 (4)0.7888 (3)0.0150 (4)
C9−0.00452 (10)1.1301 (4)0.6937 (3)0.0143 (4)
C100.21539 (11)1.0393 (4)0.9027 (3)0.0171 (5)
H10.15721.36760.71930.0197*
H2−0.04350.61910.87370.0190*
H3−0.15960.69990.74540.0221*
H4−0.17831.05090.58640.0231*
H5−0.08151.32340.55460.0200*
H60.19090.76841.00770.0276*
U11U22U33U12U13U23
O10.0147 (7)0.0167 (7)0.0185 (7)−0.0005 (6)0.0009 (6)0.0031 (6)
O20.0196 (7)0.0168 (7)0.0205 (8)0.0020 (6)−0.0015 (6)0.0056 (6)
O30.0172 (7)0.0263 (9)0.0251 (8)0.0013 (7)−0.0030 (6)0.0042 (7)
O40.0167 (7)0.0240 (8)0.0290 (9)−0.0021 (7)−0.0005 (6)−0.0028 (7)
C10.0129 (9)0.0190 (10)0.0176 (10)0.0012 (8)0.0020 (8)−0.0018 (8)
C20.0147 (9)0.0156 (10)0.0140 (9)0.0006 (8)0.0026 (8)−0.0008 (8)
C30.0164 (9)0.0154 (10)0.0118 (9)0.0013 (8)0.0015 (7)−0.0044 (8)
C40.0174 (9)0.0144 (10)0.0156 (10)−0.0001 (8)0.0017 (8)−0.0006 (8)
C50.0153 (9)0.0201 (10)0.0200 (10)−0.0037 (8)0.0018 (8)−0.0022 (9)
C60.0165 (10)0.0250 (11)0.0160 (10)0.0046 (9)−0.0018 (8)−0.0042 (9)
C70.0197 (9)0.0155 (10)0.0147 (9)0.0043 (8)−0.0009 (8)−0.0011 (8)
C80.0159 (9)0.0154 (10)0.0139 (9)0.0002 (8)0.0020 (7)−0.0022 (8)
C90.0154 (9)0.0143 (10)0.0135 (9)−0.0013 (8)0.0026 (7)−0.0015 (8)
C100.0167 (10)0.0203 (11)0.0141 (9)0.0036 (8)−0.0004 (8)−0.0041 (9)
O1—C11.344 (3)C5—C61.402 (3)
O1—C91.379 (3)C6—C71.377 (3)
O2—C31.248 (3)C7—C91.390 (3)
O3—C101.323 (3)C8—C91.397 (3)
O4—C101.213 (3)O3—H60.840
C1—C21.348 (3)C1—H10.950
C2—C31.445 (3)C4—H20.950
C2—C101.497 (3)C5—H30.950
C3—C81.464 (3)C6—H40.950
C4—C51.384 (3)C7—H50.950
C4—C81.404 (3)
O1···C32.843 (3)H3···H42.3436
O2···O32.570 (3)H4···H52.3300
O2···C13.573 (3)O1···H2i3.0150
O2···C42.865 (3)O1···H5xii2.8421
O2···C102.915 (3)O2···H1iii2.8607
O3···C32.828 (3)O2···H2iv2.4493
O4···C12.798 (3)O2···H3iv3.4273
C1···C73.589 (3)O3···H1vi2.7625
C1···C82.758 (3)O3···H3v3.4773
C2···C92.770 (3)O3···H3vii2.7495
C4···C72.804 (3)O3···H4v3.5090
C5···C92.762 (3)O3···H4vii2.8526
C6···C82.786 (3)O4···H1vi2.4100
O1···O2i3.255 (3)O4···H4ix2.4481
O1···C4i3.391 (3)O4···H5ix3.0909
O1···C5ii3.547 (3)O4···H6viii3.2381
O1···C6ii3.384 (3)C1···H2v3.5240
O1···C7ii3.537 (3)C1···H4ii3.3137
O2···O1iii3.255 (3)C1···H5xii3.3703
O2···C1iii3.035 (3)C2···H2v3.4555
O2···C4iv3.298 (3)C2···H4ii3.5224
O2···C7v3.550 (3)C3···H1iii3.3721
O2···C8v3.562 (3)C3···H2iv3.5458
O2···C9v3.482 (3)C3···H2v3.5707
O3···O4vi3.160 (3)C3···H5ii3.5517
O3···C1vi3.447 (3)C4···H5iii3.2013
O3···C5v3.511 (3)C5···H5iii3.1424
O3···C5vii3.346 (3)C5···H6v3.4189
O3···C6v3.531 (3)C6···H1ii3.5945
O3···C6vii3.399 (3)C6···H6v3.3010
O4···O3viii3.160 (3)C7···H2i3.2116
O4···O4vi3.437 (3)C7···H3i3.4460
O4···O4viii3.437 (3)C8···H5ii3.3906
O4···C1vi3.346 (3)C9···H2i3.1673
O4···C2viii3.241 (3)C10···H1vi2.7081
O4···C6ix3.232 (3)C10···H3v3.3630
O4···C7ix3.536 (3)C10···H4ix3.2814
O4···C10viii3.002 (3)H1···O2i2.8607
C1···O2i3.035 (3)H1···O3viii2.7625
C1···O3viii3.447 (3)H1···O4viii2.4100
C1···O4viii3.346 (3)H1···C3i3.3721
C1···C6ii3.386 (4)H1···C6ii3.5945
C2···O4vi3.241 (3)H1···C10viii2.7081
C2···C4v3.478 (4)H1···H4ii3.4096
C2···C5v3.588 (4)H1···H5xii3.0597
C3···C4v3.356 (3)H1···H6i3.2466
C3···C8v3.454 (3)H1···H6viii3.3979
C4···O1iii3.391 (3)H2···O1iii3.0150
C4···O2iv3.298 (3)H2···O2iv2.4493
C4···C2v3.478 (4)H2···C1v3.5240
C4···C3v3.356 (3)H2···C2v3.4555
C4···C7iii3.580 (4)H2···C3iv3.5458
C5···O1ii3.547 (3)H2···C3v3.5707
C5···O3v3.511 (3)H2···C7iii3.2116
C5···O3x3.346 (3)H2···C9iii3.1673
C5···C2v3.588 (4)H2···H2iv2.8347
C5···C10v3.556 (4)H2···H5iii3.0909
C6···O1ii3.384 (3)H2···H6iv3.5767
C6···O3v3.531 (3)H3···O2iv3.4273
C6···O3x3.399 (3)H3···O3v3.4773
C6···O4xi3.232 (3)H3···O3x2.7495
C6···C1ii3.386 (4)H3···C7iii3.4460
C7···O1ii3.537 (3)H3···C10v3.3630
C7···O2v3.550 (3)H3···H4xiii3.3726
C7···O4xi3.536 (3)H3···H5iii2.9785
C7···C4i3.580 (4)H3···H6iv3.3289
C7···C8ii3.565 (4)H3···H6x3.2355
C7···C9ii3.394 (4)H4···O3v3.5090
C8···O2v3.562 (3)H4···O3x2.8526
C8···C3v3.454 (3)H4···O4xi2.4481
C8···C7ii3.565 (4)H4···C1ii3.3137
C8···C8v3.519 (4)H4···C2ii3.5224
C9···O2v3.482 (3)H4···C10xi3.2814
C9···C7ii3.394 (4)H4···H1ii3.4096
C9···C9ii3.434 (4)H4···H3xiv3.3726
C10···O4vi3.002 (3)H4···H6v3.4215
C10···C5v3.556 (4)H4···H6x2.9941
O1···H52.5280H5···O1xii2.8421
O2···H22.6023H5···O4xi3.0909
O2···H61.7919H5···C1xii3.3703
O4···H12.4544H5···C3ii3.5517
O4···H62.8847H5···C4i3.2013
C2···H62.3211H5···C5i3.1424
C3···H13.2756H5···C8ii3.3906
C3···H22.6839H5···H1xii3.0597
C3···H62.3046H5···H2i3.0909
C4···H43.2675H5···H3i2.9785
C5···H53.2769H6···O4vi3.2381
C6···H23.2735H6···C5v3.4189
C7···H33.2685H6···C6v3.3010
C8···H33.2704H6···H1iii3.2466
C8···H53.2912H6···H1vi3.3979
C9···H13.1956H6···H2iv3.5767
C9···H23.2716H6···H3iv3.3289
C9···H43.2400H6···H3vii3.2355
C10···H12.5390H6···H4v3.4215
H2···H32.3338H6···H4vii2.9941
C1—O1—C9118.80 (16)O1—C9—C8121.58 (17)
O1—C1—C2124.29 (18)C7—C9—C8121.78 (18)
C1—C2—C3120.57 (17)O3—C10—O4121.07 (19)
C1—C2—C10117.90 (18)O3—C10—C2115.74 (18)
C3—C2—C10121.53 (17)O4—C10—C2123.19 (19)
O2—C3—C2122.87 (17)C10—O3—H6109.466
O2—C3—C8121.96 (17)O1—C1—H1117.850
C2—C3—C8115.17 (17)C2—C1—H1117.864
C5—C4—C8119.74 (19)C5—C4—H2120.128
C4—C5—C6120.23 (19)C8—C4—H2120.133
C5—C6—C7120.86 (19)C4—C5—H3119.885
C6—C7—C9118.65 (19)C6—C5—H3119.886
C3—C8—C4121.68 (18)C5—C6—H4119.563
C3—C8—C9119.59 (17)C7—C6—H4119.572
C4—C8—C9118.73 (17)C6—C7—H5120.665
O1—C9—C7116.64 (17)C9—C7—H5120.682
C1—O1—C9—C7−179.46 (15)C5—C4—C8—C90.6 (3)
C1—O1—C9—C80.1 (3)C8—C4—C5—C6−0.5 (3)
C9—O1—C1—C2−0.4 (3)C8—C4—C5—H3179.5
C9—O1—C1—H1179.6H2—C4—C5—C6179.5
H6—O3—C10—O4−179.4H2—C4—C5—H3−0.5
H6—O3—C10—C21.5H2—C4—C8—C30.2
O1—C1—C2—C3−0.1 (3)H2—C4—C8—C9−179.4
O1—C1—C2—C10−179.20 (16)C4—C5—C6—C7−0.1 (3)
H1—C1—C2—C3179.9C4—C5—C6—H4180.0
H1—C1—C2—C100.8H3—C5—C6—C7180.0
C1—C2—C3—O2179.94 (17)H3—C5—C6—H4−0.0
C1—C2—C3—C80.9 (3)C5—C6—C7—C90.5 (3)
C1—C2—C10—O3176.58 (17)C5—C6—C7—H5−179.5
C1—C2—C10—O4−2.5 (3)H4—C6—C7—C9−179.5
C3—C2—C10—O3−2.5 (3)H4—C6—C7—H50.5
C3—C2—C10—O4178.41 (17)C6—C7—C9—O1179.18 (17)
C10—C2—C3—O2−1.0 (3)C6—C7—C9—C8−0.4 (3)
C10—C2—C3—C8179.91 (15)H5—C7—C9—O1−0.8
O2—C3—C8—C40.2 (3)H5—C7—C9—C8179.6
O2—C3—C8—C9179.82 (16)C3—C8—C9—O10.6 (3)
C2—C3—C8—C4179.26 (15)C3—C8—C9—C7−179.78 (16)
C2—C3—C8—C9−1.1 (3)C4—C8—C9—O1−179.71 (16)
C5—C4—C8—C3−179.76 (16)C4—C8—C9—C7−0.1 (3)
D—H···AD—HH···AD···AD—H···A
O3—H6···O20.841.792.570 (3)153
C4—H2···O2iv0.952.453.298 (3)149
C1—H1···O4viii0.952.413.346 (3)168
C6—H4···O4xi0.952.453.232 (3)140
Table 1

Hydrogen-bond geometry (, )

DHA DHHA D A DHA
O3H6O20.841.792.570(3)153
C4H2O2i 0.952.453.298(3)149
C1H1O4ii 0.952.413.346(3)168
C6H4O4iii 0.952.453.232(3)140

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

  5 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.  Chromone-2- and -3-carboxylic acids inhibit differently monoamine oxidases A and B.

Authors:  Stefano Alcaro; Alexandra Gaspar; Francesco Ortuso; Nuno Milhazes; Francisco Orallo; Eugenio Uriarte; Matilde Yáñez; Fernanda Borges
Journal:  Bioorg Med Chem Lett       Date:  2010-03-27       Impact factor: 2.823

3.  Discovery of novel A3 adenosine receptor ligands based on chromone scaffold.

Authors:  Alexandra Gaspar; Joana Reis; Sonja Kachler; Silvia Paoletta; Eugenio Uriarte; Karl-Norbert Klotz; Stefano Moro; Fernanda Borges
Journal:  Biochem Pharmacol       Date:  2012-03-17       Impact factor: 5.858

4.  Combining QSAR classification models for predictive modeling of human monoamine oxidase inhibitors.

Authors:  Aliuska Morales Helguera; Alfonso Pérez-Garrido; Alexandra Gaspar; Joana Reis; Fernando Cagide; Dolores Vina; M Natália D S Cordeiro; Fernanda Borges
Journal:  Eur J Med Chem       Date:  2012-11-01       Impact factor: 6.514

5.  Selected chromone derivatives as inhibitors of monoamine oxidase.

Authors:  Lesetja J Legoabe; Anél Petzer; Jacobus P Petzer
Journal:  Bioorg Med Chem Lett       Date:  2012-07-14       Impact factor: 2.823
  5 in total

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