organic compounds
H-chromene-3-carboxylic acid
of 4-oxo-4aSchool of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan
*Correspondence e-mail: ishi206@u-shizuoka-ken.ac.jp
In the title compound, C10H6O4, also known as 3-carboxychromone, 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 carboxy group is 3.06 (2)°. An intramolecular hydrogen bond is formed between the ring carbonyl O atom and the carboxy O—H atom, closing an S(6) loop. In the crystal, molecules are assembled by stacking interactions [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 carboxy O and C atoms [C=O⋯C=O = 3.002 (3) Å].
Keywords: crystal structure; chromone; hydrogen bonding; stacking interaction.
CCDC reference: 1412580
1. 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).
2. Experimental
2.1. Crystal data
|
2.2. Data collection
|
2.3. Refinement
|
Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell 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.
Supporting information
CCDC reference: 1412580
https://doi.org/10.1107/S2056989015013456/tk5375sup1.cif
contains datablocks General, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015013456/tk5375Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015013456/tk5375Isup3.cml
The title compound was synthesized from 3-formylchromone according to the literature method (Helguera et al. 2013). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an acetone solution of the title compound at room temperature.
All hydrogen atoms were placed in geometric positions [C–H 0.95 Å and O–H 0.84 Å], and refined using a riding model with Uiso(H) = 1.2Ueq of the parent atoms.
The title compound (3-carboxychromone) and its derivatives are reported as monoamine oxidase inhibitors (Alcaro et al., 2010; Legoabe et al., 2012), A3 adenosine receptor ligands (Gaspar et al., 2012) and tumor necrosis factor inhibitors (Papaneophytou et al., 2015).
The mean deviation of the least-square planes for the non-H atoms of the chromone ring is 0.0057 Å, and the largest deviation is 0.011 (2) Å for C2. These mean that these atoms are essentially coplanar (Fig. 1). The dihedral angle between the fused-ring and carboxy plane is 3.06 (2)°. Intramolecular hydrogen bond is formed between the α,β-unsaturated carbonyl O atom and the carboxy O—H atom.
In the crystal packing, the molecules are assembled by stacking interactions [centroid–centroid distance between the benzene and pyran rings of the 4H-chromene units = 3.844 (3) Å] and C–H···O hydrogen bonds, as shown in Fig. 2. Shorter contacts than the sum of van der Waals radii are observed between the carboxy O4 and C10i atoms [O4···C10i = 3.002 (3) Å, i: –x + 1, y + 1/2, –z + 3/2].
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).
Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell
WinAFC Diffractometer Control Software (Rigaku, 1999); data reduction: WinAFC Diffractometer Control Software (Rigaku, 1999); 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 (Rigaku, 2010).Fig. 1. 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. | |
Fig. 2. 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. |
C10H6O4 | F(000) = 392.00 |
Mr = 190.15 | Dx = 1.577 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 18.017 (8) Å | θ = 15.0–17.3° |
b = 5.549 (3) Å | µ = 0.12 mm−1 |
c = 8.017 (5) Å | T = 100 K |
β = 92.49 (4)° | Plate, colourless |
V = 800.8 (8) Å3 | 0.37 × 0.35 × 0.05 mm |
Z = 4 |
Rigaku AFC-7R diffractometer | θmax = 27.5° |
ω–2θ scans | h = −23→23 |
2228 measured reflections | k = 0→7 |
1831 independent reflections | l = −10→5 |
1183 reflections with F2 > 2.0σ(F2) | 3 standard reflections every 150 reflections |
Rint = 0.098 | intensity decay: −1.6% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0605P)2 + 0.0457P] where P = (Fo2 + 2Fc2)/3 |
1831 reflections | (Δ/σ)max < 0.001 |
128 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Primary atom site location: structure-invariant direct methods |
C10H6O4 | V = 800.8 (8) Å3 |
Mr = 190.15 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 18.017 (8) Å | µ = 0.12 mm−1 |
b = 5.549 (3) Å | T = 100 K |
c = 8.017 (5) Å | 0.37 × 0.35 × 0.05 mm |
β = 92.49 (4)° |
Rigaku AFC-7R diffractometer | Rint = 0.098 |
2228 measured reflections | 3 standard reflections every 150 reflections |
1831 independent reflections | intensity decay: −1.6% |
1183 reflections with F2 > 2.0σ(F2) |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.24 e Å−3 |
1831 reflections | Δρmin = −0.24 e Å−3 |
128 parameters |
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). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.05120 (7) | 1.2950 (3) | 0.66885 (17) | 0.0166 (4) | |
O2 | 0.09613 (7) | 0.6952 (3) | 0.95238 (17) | 0.0190 (4) | |
O3 | 0.22945 (8) | 0.8524 (3) | 1.00156 (19) | 0.0230 (4) | |
O4 | 0.26339 (8) | 1.1851 (3) | 0.87416 (19) | 0.0233 (4) | |
C1 | 0.11926 (10) | 1.2529 (4) | 0.7381 (3) | 0.0165 (5) | |
C2 | 0.13725 (10) | 1.0587 (4) | 0.8324 (3) | 0.0147 (4) | |
C3 | 0.08209 (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) | |
C8 | 0.00821 (10) | 0.9221 (4) | 0.7888 (3) | 0.0150 (4) | |
C9 | −0.00452 (10) | 1.1301 (4) | 0.6937 (3) | 0.0143 (4) | |
C10 | 0.21539 (11) | 1.0393 (4) | 0.9027 (3) | 0.0171 (5) | |
H1 | 0.1572 | 1.3676 | 0.7193 | 0.0197* | |
H2 | −0.0435 | 0.6191 | 0.8737 | 0.0190* | |
H3 | −0.1596 | 0.6999 | 0.7454 | 0.0221* | |
H4 | −0.1783 | 1.0509 | 0.5864 | 0.0231* | |
H5 | −0.0815 | 1.3234 | 0.5546 | 0.0200* | |
H6 | 0.1909 | 0.7684 | 1.0077 | 0.0276* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0147 (7) | 0.0167 (7) | 0.0185 (7) | −0.0005 (6) | 0.0009 (6) | 0.0031 (6) |
O2 | 0.0196 (7) | 0.0168 (7) | 0.0205 (8) | 0.0020 (6) | −0.0015 (6) | 0.0056 (6) |
O3 | 0.0172 (7) | 0.0263 (9) | 0.0251 (8) | 0.0013 (7) | −0.0030 (6) | 0.0042 (7) |
O4 | 0.0167 (7) | 0.0240 (8) | 0.0290 (9) | −0.0021 (7) | −0.0005 (6) | −0.0028 (7) |
C1 | 0.0129 (9) | 0.0190 (10) | 0.0176 (10) | 0.0012 (8) | 0.0020 (8) | −0.0018 (8) |
C2 | 0.0147 (9) | 0.0156 (10) | 0.0140 (9) | 0.0006 (8) | 0.0026 (8) | −0.0008 (8) |
C3 | 0.0164 (9) | 0.0154 (10) | 0.0118 (9) | 0.0013 (8) | 0.0015 (7) | −0.0044 (8) |
C4 | 0.0174 (9) | 0.0144 (10) | 0.0156 (10) | −0.0001 (8) | 0.0017 (8) | −0.0006 (8) |
C5 | 0.0153 (9) | 0.0201 (10) | 0.0200 (10) | −0.0037 (8) | 0.0018 (8) | −0.0022 (9) |
C6 | 0.0165 (10) | 0.0250 (11) | 0.0160 (10) | 0.0046 (9) | −0.0018 (8) | −0.0042 (9) |
C7 | 0.0197 (9) | 0.0155 (10) | 0.0147 (9) | 0.0043 (8) | −0.0009 (8) | −0.0011 (8) |
C8 | 0.0159 (9) | 0.0154 (10) | 0.0139 (9) | 0.0002 (8) | 0.0020 (7) | −0.0022 (8) |
C9 | 0.0154 (9) | 0.0143 (10) | 0.0135 (9) | −0.0013 (8) | 0.0026 (7) | −0.0015 (8) |
C10 | 0.0167 (10) | 0.0203 (11) | 0.0141 (9) | 0.0036 (8) | −0.0004 (8) | −0.0041 (9) |
O1—C1 | 1.344 (3) | C5—C6 | 1.402 (3) |
O1—C9 | 1.379 (3) | C6—C7 | 1.377 (3) |
O2—C3 | 1.248 (3) | C7—C9 | 1.390 (3) |
O3—C10 | 1.323 (3) | C8—C9 | 1.397 (3) |
O4—C10 | 1.213 (3) | O3—H6 | 0.840 |
C1—C2 | 1.348 (3) | C1—H1 | 0.950 |
C2—C3 | 1.445 (3) | C4—H2 | 0.950 |
C2—C10 | 1.497 (3) | C5—H3 | 0.950 |
C3—C8 | 1.464 (3) | C6—H4 | 0.950 |
C4—C5 | 1.384 (3) | C7—H5 | 0.950 |
C4—C8 | 1.404 (3) | ||
O1···C3 | 2.843 (3) | H3···H4 | 2.3436 |
O2···O3 | 2.570 (3) | H4···H5 | 2.3300 |
O2···C1 | 3.573 (3) | O1···H2i | 3.0150 |
O2···C4 | 2.865 (3) | O1···H5xii | 2.8421 |
O2···C10 | 2.915 (3) | O2···H1iii | 2.8607 |
O3···C3 | 2.828 (3) | O2···H2iv | 2.4493 |
O4···C1 | 2.798 (3) | O2···H3iv | 3.4273 |
C1···C7 | 3.589 (3) | O3···H1vi | 2.7625 |
C1···C8 | 2.758 (3) | O3···H3v | 3.4773 |
C2···C9 | 2.770 (3) | O3···H3vii | 2.7495 |
C4···C7 | 2.804 (3) | O3···H4v | 3.5090 |
C5···C9 | 2.762 (3) | O3···H4vii | 2.8526 |
C6···C8 | 2.786 (3) | O4···H1vi | 2.4100 |
O1···O2i | 3.255 (3) | O4···H4ix | 2.4481 |
O1···C4i | 3.391 (3) | O4···H5ix | 3.0909 |
O1···C5ii | 3.547 (3) | O4···H6viii | 3.2381 |
O1···C6ii | 3.384 (3) | C1···H2v | 3.5240 |
O1···C7ii | 3.537 (3) | C1···H4ii | 3.3137 |
O2···O1iii | 3.255 (3) | C1···H5xii | 3.3703 |
O2···C1iii | 3.035 (3) | C2···H2v | 3.4555 |
O2···C4iv | 3.298 (3) | C2···H4ii | 3.5224 |
O2···C7v | 3.550 (3) | C3···H1iii | 3.3721 |
O2···C8v | 3.562 (3) | C3···H2iv | 3.5458 |
O2···C9v | 3.482 (3) | C3···H2v | 3.5707 |
O3···O4vi | 3.160 (3) | C3···H5ii | 3.5517 |
O3···C1vi | 3.447 (3) | C4···H5iii | 3.2013 |
O3···C5v | 3.511 (3) | C5···H5iii | 3.1424 |
O3···C5vii | 3.346 (3) | C5···H6v | 3.4189 |
O3···C6v | 3.531 (3) | C6···H1ii | 3.5945 |
O3···C6vii | 3.399 (3) | C6···H6v | 3.3010 |
O4···O3viii | 3.160 (3) | C7···H2i | 3.2116 |
O4···O4vi | 3.437 (3) | C7···H3i | 3.4460 |
O4···O4viii | 3.437 (3) | C8···H5ii | 3.3906 |
O4···C1vi | 3.346 (3) | C9···H2i | 3.1673 |
O4···C2viii | 3.241 (3) | C10···H1vi | 2.7081 |
O4···C6ix | 3.232 (3) | C10···H3v | 3.3630 |
O4···C7ix | 3.536 (3) | C10···H4ix | 3.2814 |
O4···C10viii | 3.002 (3) | H1···O2i | 2.8607 |
C1···O2i | 3.035 (3) | H1···O3viii | 2.7625 |
C1···O3viii | 3.447 (3) | H1···O4viii | 2.4100 |
C1···O4viii | 3.346 (3) | H1···C3i | 3.3721 |
C1···C6ii | 3.386 (4) | H1···C6ii | 3.5945 |
C2···O4vi | 3.241 (3) | H1···C10viii | 2.7081 |
C2···C4v | 3.478 (4) | H1···H4ii | 3.4096 |
C2···C5v | 3.588 (4) | H1···H5xii | 3.0597 |
C3···C4v | 3.356 (3) | H1···H6i | 3.2466 |
C3···C8v | 3.454 (3) | H1···H6viii | 3.3979 |
C4···O1iii | 3.391 (3) | H2···O1iii | 3.0150 |
C4···O2iv | 3.298 (3) | H2···O2iv | 2.4493 |
C4···C2v | 3.478 (4) | H2···C1v | 3.5240 |
C4···C3v | 3.356 (3) | H2···C2v | 3.4555 |
C4···C7iii | 3.580 (4) | H2···C3iv | 3.5458 |
C5···O1ii | 3.547 (3) | H2···C3v | 3.5707 |
C5···O3v | 3.511 (3) | H2···C7iii | 3.2116 |
C5···O3x | 3.346 (3) | H2···C9iii | 3.1673 |
C5···C2v | 3.588 (4) | H2···H2iv | 2.8347 |
C5···C10v | 3.556 (4) | H2···H5iii | 3.0909 |
C6···O1ii | 3.384 (3) | H2···H6iv | 3.5767 |
C6···O3v | 3.531 (3) | H3···O2iv | 3.4273 |
C6···O3x | 3.399 (3) | H3···O3v | 3.4773 |
C6···O4xi | 3.232 (3) | H3···O3x | 2.7495 |
C6···C1ii | 3.386 (4) | H3···C7iii | 3.4460 |
C7···O1ii | 3.537 (3) | H3···C10v | 3.3630 |
C7···O2v | 3.550 (3) | H3···H4xiii | 3.3726 |
C7···O4xi | 3.536 (3) | H3···H5iii | 2.9785 |
C7···C4i | 3.580 (4) | H3···H6iv | 3.3289 |
C7···C8ii | 3.565 (4) | H3···H6x | 3.2355 |
C7···C9ii | 3.394 (4) | H4···O3v | 3.5090 |
C8···O2v | 3.562 (3) | H4···O3x | 2.8526 |
C8···C3v | 3.454 (3) | H4···O4xi | 2.4481 |
C8···C7ii | 3.565 (4) | H4···C1ii | 3.3137 |
C8···C8v | 3.519 (4) | H4···C2ii | 3.5224 |
C9···O2v | 3.482 (3) | H4···C10xi | 3.2814 |
C9···C7ii | 3.394 (4) | H4···H1ii | 3.4096 |
C9···C9ii | 3.434 (4) | H4···H3xiv | 3.3726 |
C10···O4vi | 3.002 (3) | H4···H6v | 3.4215 |
C10···C5v | 3.556 (4) | H4···H6x | 2.9941 |
O1···H5 | 2.5280 | H5···O1xii | 2.8421 |
O2···H2 | 2.6023 | H5···O4xi | 3.0909 |
O2···H6 | 1.7919 | H5···C1xii | 3.3703 |
O4···H1 | 2.4544 | H5···C3ii | 3.5517 |
O4···H6 | 2.8847 | H5···C4i | 3.2013 |
C2···H6 | 2.3211 | H5···C5i | 3.1424 |
C3···H1 | 3.2756 | H5···C8ii | 3.3906 |
C3···H2 | 2.6839 | H5···H1xii | 3.0597 |
C3···H6 | 2.3046 | H5···H2i | 3.0909 |
C4···H4 | 3.2675 | H5···H3i | 2.9785 |
C5···H5 | 3.2769 | H6···O4vi | 3.2381 |
C6···H2 | 3.2735 | H6···C5v | 3.4189 |
C7···H3 | 3.2685 | H6···C6v | 3.3010 |
C8···H3 | 3.2704 | H6···H1iii | 3.2466 |
C8···H5 | 3.2912 | H6···H1vi | 3.3979 |
C9···H1 | 3.1956 | H6···H2iv | 3.5767 |
C9···H2 | 3.2716 | H6···H3iv | 3.3289 |
C9···H4 | 3.2400 | H6···H3vii | 3.2355 |
C10···H1 | 2.5390 | H6···H4v | 3.4215 |
H2···H3 | 2.3338 | H6···H4vii | 2.9941 |
C1—O1—C9 | 118.80 (16) | O1—C9—C8 | 121.58 (17) |
O1—C1—C2 | 124.29 (18) | C7—C9—C8 | 121.78 (18) |
C1—C2—C3 | 120.57 (17) | O3—C10—O4 | 121.07 (19) |
C1—C2—C10 | 117.90 (18) | O3—C10—C2 | 115.74 (18) |
C3—C2—C10 | 121.53 (17) | O4—C10—C2 | 123.19 (19) |
O2—C3—C2 | 122.87 (17) | C10—O3—H6 | 109.466 |
O2—C3—C8 | 121.96 (17) | O1—C1—H1 | 117.850 |
C2—C3—C8 | 115.17 (17) | C2—C1—H1 | 117.864 |
C5—C4—C8 | 119.74 (19) | C5—C4—H2 | 120.128 |
C4—C5—C6 | 120.23 (19) | C8—C4—H2 | 120.133 |
C5—C6—C7 | 120.86 (19) | C4—C5—H3 | 119.885 |
C6—C7—C9 | 118.65 (19) | C6—C5—H3 | 119.886 |
C3—C8—C4 | 121.68 (18) | C5—C6—H4 | 119.563 |
C3—C8—C9 | 119.59 (17) | C7—C6—H4 | 119.572 |
C4—C8—C9 | 118.73 (17) | C6—C7—H5 | 120.665 |
O1—C9—C7 | 116.64 (17) | C9—C7—H5 | 120.682 |
C1—O1—C9—C7 | −179.46 (15) | C5—C4—C8—C9 | 0.6 (3) |
C1—O1—C9—C8 | 0.1 (3) | C8—C4—C5—C6 | −0.5 (3) |
C9—O1—C1—C2 | −0.4 (3) | C8—C4—C5—H3 | 179.5 |
C9—O1—C1—H1 | 179.6 | H2—C4—C5—C6 | 179.5 |
H6—O3—C10—O4 | −179.4 | H2—C4—C5—H3 | −0.5 |
H6—O3—C10—C2 | 1.5 | H2—C4—C8—C3 | 0.2 |
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—C3 | 179.9 | C4—C5—C6—H4 | 180.0 |
H1—C1—C2—C10 | 0.8 | H3—C5—C6—C7 | 180.0 |
C1—C2—C3—O2 | 179.94 (17) | H3—C5—C6—H4 | −0.0 |
C1—C2—C3—C8 | 0.9 (3) | C5—C6—C7—C9 | 0.5 (3) |
C1—C2—C10—O3 | 176.58 (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—H5 | 0.5 |
C3—C2—C10—O4 | 178.41 (17) | C6—C7—C9—O1 | 179.18 (17) |
C10—C2—C3—O2 | −1.0 (3) | C6—C7—C9—C8 | −0.4 (3) |
C10—C2—C3—C8 | 179.91 (15) | H5—C7—C9—O1 | −0.8 |
O2—C3—C8—C4 | 0.2 (3) | H5—C7—C9—C8 | 179.6 |
O2—C3—C8—C9 | 179.82 (16) | C3—C8—C9—O1 | 0.6 (3) |
C2—C3—C8—C4 | 179.26 (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) |
Symmetry codes: (i) x, y+1, z; (ii) −x, −y+2, −z+1; (iii) x, y−1, z; (iv) −x, −y+1, −z+2; (v) −x, −y+2, −z+2; (vi) −x+1/2, y−1/2, −z+3/2; (vii) x+1/2, −y+3/2, z+1/2; (viii) −x+1/2, y+1/2, −z+3/2; (ix) x+1/2, −y+5/2, z+1/2; (x) x−1/2, −y+3/2, z−1/2; (xi) x−1/2, −y+5/2, z−1/2; (xii) −x, −y+3, −z+1; (xiii) −x−1/2, y−1/2, −z+3/2; (xiv) −x−1/2, y+1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H6···O2 | 0.84 | 1.79 | 2.570 (3) | 153 |
C4—H2···O2iv | 0.95 | 2.45 | 3.298 (3) | 149 |
C1—H1···O4viii | 0.95 | 2.41 | 3.346 (3) | 168 |
C6—H4···O4xi | 0.95 | 2.45 | 3.232 (3) | 140 |
Symmetry codes: (iv) −x, −y+1, −z+2; (viii) −x+1/2, y+1/2, −z+3/2; (xi) x−1/2, −y+5/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H6···O2 | 0.84 | 1.79 | 2.570 (3) | 153 |
C4—H2···O2i | 0.95 | 2.45 | 3.298 (3) | 149 |
C1—H1···O4ii | 0.95 | 2.41 | 3.346 (3) | 168 |
C6—H4···O4iii | 0.95 | 2.45 | 3.232 (3) | 140 |
Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x+1/2, y+1/2, −z+3/2; (iii) x−1/2, −y+5/2, z−1/2. |
Acknowledgements
The University of Shizuoka is acknowledged for instrumental support.
References
Alcaro, S., Gaspar, A., Ortuso, F., Milhazes, N., Orallo, F., Uriarte, E., Yáñez, M. & Borges, F. (2010). Bioorg. Med. Chem. Lett. 20, 2709–2712. Web of Science CrossRef CAS PubMed Google Scholar
Gaspar, A., Reis, J., Kachler, S., Paoletta, S., Uriarte, E., Klotz, K. N., Moro, S. & Borges, F. (2012). Biochem. Pharmacol. 84, 21–29. Web of Science CrossRef CAS PubMed Google Scholar
Helguera, A. M., Pérez-Garrido, A., Gaspar, A., Reis, J., Cagide, F., Vina, D., Cordeiro, M. N. & Borges, F. (2013). Eur. J. Med. Chem. 59, 75–90. Web of Science CrossRef CAS PubMed Google Scholar
Legoabe, L. J., Petzer, A. & Petzer, J. P. (2012). Bioorg. Med. Chem. Lett. 22, 5480–5484. Web of Science CrossRef CAS PubMed Google Scholar
Papaneophytou, C., Alexiou, P., Papakyriakou, A., Ntougkos, E., Tsiliouka, K., Maranti, A., Liepouri, F., Strongilos, A., Mettou, A., Couladouros, E., Eliopoulos, E., Douni, E., Kollias, G. & Kontopidis, G. (2015). Med. Chem. Commun. 6, 1196–1209. Web of Science CrossRef CAS Google Scholar
Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The title compound (3-carboxychromone) and its derivatives are reported as monoamine oxidase inhibitors (Alcaro et al., 2010; Legoabe et al., 2012), A3 adenosine receptor ligands (Gaspar et al., 2012) and tumor necrosis factor inhibitors (Papaneophytou et al., 2015).
The mean deviation of the least-square planes for the non-H atoms of the chromone ring is 0.0057 Å, and the largest deviation is 0.011 (2) Å for C2. These mean that these atoms are essentially coplanar (Fig. 1). The dihedral angle between the fused-ring and carboxy plane is 3.06 (2)°. Intramolecular hydrogen bond is formed between the α,β-unsaturated carbonyl O atom and the carboxy O—H atom.
In the crystal packing, the molecules are assembled by stacking interactions [centroid–centroid distance between the benzene and pyran rings of the 4H-chromene units = 3.844 (3) Å] and C–H···O hydrogen bonds, as shown in Fig. 2. Shorter contacts than the sum of van der Waals radii are observed between the carboxy O4 and C10i atoms [O4···C10i = 3.002 (3) Å, i: –x + 1, y + 1/2, –z + 3/2].