Abstract
C21H14O3, monoclinic, P21/c (no. 14), a = 4.8318(8) Å, b = 26.590(4) Å, c = 11.821(2) Å, β = 91.050(4)°, V = 1518.4(4) Å3, Z = 4, R gt (F) = 0.0401, wR ref (F) = 0.1038, T = 296(2) K.
CCDC no.: 2122345
The molecular structure is shown in the figure (H atoms are omitted for clarity). Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Data collection and handling.
Crystal: | Colorless prismatic |
Size: | 0.20 × 0.17 × 0.11 mm |
Wavelength: | Mo Kα radiation (0.71073 Å) |
μ: | 0.09 mm−1 |
Diffractometer, scan mode: | Bruker APEX-II, φ and ω |
θ max, completeness: | 25.5°, >99% |
N(hkl)measured, N(hkl)unique, R int: | 10,546, 2827, 0.036 |
Criterion for I obs, N(hkl)gt: | I obs > 2 σ(I obs), 1906 |
N(param)refined: | 219 |
Programs: | Bruker [1], SHELX [2, 3], Diamond [4] |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
Atom | x | y | Z | U iso*/U eq |
---|---|---|---|---|
O1 | 0.3744 (3) | 0.69856 (5) | 0.28643 (11) | 0.0586 (4) |
O2 | 0.3799 (3) | 0.58705 (5) | −0.02697 (11) | 0.0570 (4) |
O3 | 1.0774 (3) | 0.54301 (5) | 0.30595 (10) | 0.0456 (3) |
C1 | 0.3227 (4) | 0.67650 (7) | 0.19703 (15) | 0.0429 (4) |
C2 | 0.1111 (4) | 0.69327 (7) | 0.11098 (15) | 0.0431 (5) |
C3 | −0.0723 (4) | 0.73308 (7) | 0.11287 (18) | 0.0541 (5) |
H3 | −0.0803 | 0.7543 | 0.1753 | 0.065* |
C4 | −0.2443 (4) | 0.74058 (8) | 0.0190 (2) | 0.0618 (6) |
H4 | −0.3686 | 0.7673 | 0.0186 | 0.074* |
C5 | −0.2342 (4) | 0.70904 (8) | −0.07387 (19) | 0.0611 (6) |
H5 | −0.3503 | 0.7150 | −0.1360 | 0.073* |
C6 | −0.0529 (4) | 0.66870 (8) | −0.07529 (16) | 0.0540 (5) |
H6 | −0.0465 | 0.6472 | −0.1373 | 0.065* |
C7 | 0.1183 (4) | 0.66127 (7) | 0.01821 (15) | 0.0432 (5) |
C8 | 0.3279 (4) | 0.62090 (7) | 0.04012 (15) | 0.0423 (5) |
C9 | 0.4515 (4) | 0.63068 (7) | 0.15223 (14) | 0.0394 (4) |
C10 | 0.6583 (4) | 0.60203 (7) | 0.20438 (14) | 0.0384 (4) |
C11 | 0.7664 (4) | 0.55744 (7) | 0.15314 (15) | 0.0435 (5) |
H11 | 0.6961 | 0.5475 | 0.0829 | 0.052* |
C12 | 0.9650 (4) | 0.52973 (7) | 0.20296 (15) | 0.0433 (5) |
C13 | 0.9838 (4) | 0.58547 (7) | 0.35889 (14) | 0.0403 (4) |
C14 | 0.7813 (4) | 0.61401 (7) | 0.31254 (14) | 0.0420 (4) |
H14 | 0.7197 | 0.6421 | 0.3515 | 0.050* |
C15 | 1.1289 (4) | 0.59319 (7) | 0.46811 (14) | 0.0417 (4) |
C16 | 1.2577 (4) | 0.55315 (8) | 0.52314 (16) | 0.0553 (5) |
H16 | 1.2550 | 0.5214 | 0.4900 | 0.066* |
C17 | 1.3896 (5) | 0.55996 (9) | 0.62656 (17) | 0.0668 (6) |
H17 | 1.4735 | 0.5328 | 0.6628 | 0.080* |
C18 | 1.3978 (5) | 0.60674 (9) | 0.67637 (17) | 0.0647 (6) |
H18 | 1.4854 | 0.6112 | 0.7464 | 0.078* |
C19 | 1.2755 (5) | 0.64668 (9) | 0.62188 (17) | 0.0659 (6) |
H19 | 1.2823 | 0.6784 | 0.6549 | 0.079* |
C20 | 1.1419 (5) | 0.64027 (8) | 0.51812 (16) | 0.0563 (6) |
H20 | 1.0606 | 0.6677 | 0.4819 | 0.068* |
C21 | 1.0929 (5) | 0.48308 (7) | 0.15918 (17) | 0.0571 (6) |
H21A | 0.9887 | 0.4714 | 0.0945 | 0.086* |
H21B | 1.0930 | 0.4577 | 0.2170 | 0.086* |
H21C | 1.2798 | 0.4899 | 0.1377 | 0.086* |
Source of material
The title compound was prepared according to the synthetic method reported in the previous literature [5]. Crystals were obtained by slow evaporation from a mixture of ethyl acetate and ethanol.
Experimental details
H atoms were positioned geometrically and refined using a riding model, with U iso(H) = 1.5 U eq(C) for methyl H atoms and 1.2 U eq(C) for all other H atoms. All the non-hydrogen atoms were refined anisotropically.
Comment
The 4H-pyran unit has been demonstrated to be an excellent building block for constructing various organic fluorescent materials in the field of fluorescence sensors, security systems, and optical information storage [6, 7]. Furthermore, the researchers have also found that the intermolecular interactions and stacking arrangements often exhibit a very important influence on the photophysical properties of the materials [8]. Therefore, the investigation on the crystal structures of 4H-pyran derivatives has received wide attention [9], [10], [11].
In the title structure the 1H-indene-1,3(2H)-dione moiety and the 4H-pyran ring are almost in the same plane. The dihedral angle between the 4H-pyran ring and phenyl ring is determined to be 22.4°. This result indicates that the asymmetric molecule has a twisted molecular conformation, which causes that no obvious π···π interactions are observed. Similar results can be found in previously reported structures of related 4H-pyran derivatives [5, 9, 11]. The molecules are linked by one kind of C20–H20···π (benzene ring) bond with a distance of 3.570 Å and one kind of C21–H21A···O2 hydrogen bond with a distance of 2.484 Å.
Funding source: Wenzhou University
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Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
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Research funding: This study was financially supported by Wenzhou University for the publication fee.
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Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
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3. Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Suche in Google Scholar
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© 2021 An-Na Sun et al., published by De Gruyter, Berlin/Boston
This work is licensed under the Creative Commons Attribution 4.0 International License.
Artikel in diesem Heft
- Frontmatter
- New Crystal Structures
- Crystal structure of {2,2′-{cyclohexane-1,2-diylbis[(azanylylidene)methylylidene]}bis(2,4-dibromophenolato)-κ4 N,N′,O,O′}copper(II) ─ diethylformamide (1/1), C23H23Br4CuN3O3
- The crystal structure of 2-(2-methyl-6-phenyl-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione, C21H14O3
- Crystal structure of bis((1-methylbenzimidazol-2-yl)methyl)amine, C18H19N5
- Crystal structure of (E)-N′-(1-(2-hydroxy-4-methoxyphenyl)ethylidene) isonicotinohydrazide, C15H15N3O3
- Crystal structure of 2-((4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio)acetonitrile, C15H11N5S
- The crystal structure of 2,2′-((1E,1′E)-hydrazine-1,2-diylidenebis(methaneylylidene))bis(4-chlorophenol), C14H10Cl2N2O2
- Dichlorido-{2,6-bis(4,5-dihydro-1H-pyrazol-3-yl)pyridine-κ3 N,N′,N″}zinc(II), C11H9C12N5Zn
- The crystal structure of dichlorido-(2-((4-phenyl-2H-1,2,3-triazol-2-yl)methyl)pyridine-κ2N,N′)palladium(II), C14H12Cl2N4Pd
- The crystal structure of 1-(N1-benzyl-2-methyl-4-nitro-imidazol-5-yl)-4-(prop-2-yn-1-yl) piperazine, C18H21N5O2
- Crystal structure of (μ4-(1,2,4,5-tetra(1,2,4-triazol-1-ylmethyl)-benzene-κ4N:N1:N2:N3)disilver(I) diperchlorate
- The crystal structure of 1-(2-bromoethane)-4-amine-3,5-dinitropyrazole, C5H6Br1N5O4
- Crystal structure of (E)-1-(4-benzyl-3,5-dioxomorpholin-2-ylidene)ethyl acetate, C15H15N1O5
- The crystal structure of poly[diaqua-(μ2-1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ2N:N′)-bis(μ3-terephthalato-κ3O:O′:O′′)dicadmium(II)], C17H15N6O5Cd
- Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)thiophene-2-carbohydrazide, C13H11ClN2O2S
- The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylato-k2 N,O)cobalt(II)]-monohydrate, C36H26N4O5Co
- Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-3-hydroxybenzo-hydrazide monohydrate, C14H13ClN2O4
- Crystal structure of 1,1′-(methylene)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C42H30N14Ni2S8
- Crystal structure of 1,1′-(1,2-ethanediyl)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S:S)nickel(II), C20H14N6NiS4
- The crystal structure of 1-methyl-1H-pyrazol-2-ium nitrate, C4H7O3N3
- The crystal structure of 4,4′-diselanediylbis(8-(hexyloxy)-3,6-dimethyl-1-(piperidin-1-yl)isoquinoline-7-carbonitrile), C46H60N6O2Se2
- The crystal structure of tris(6-methylpyridin-2-yl)phosphine selenide, C18H18N3PSe
- The crystal structure of 1,2-bis(2,4-dinitro-1H-imidazol-1-yl)ethane ─ acetone (1/1), C11H12N8O9
- Crystal structure of [diaqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N,N′,O,O′]nickel(II)] tetrahydrate, C16H12N4NiO10·4H2O
- The crystal structure of tris(4-methyl-1H-pyrazol-1-yl)methane, C13H16N6
- The crystal structure of 5,6-dichloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H8Cl2N2O2
- Crystal structure of (E)-(2-methoxy-benzylidene)-(4-[1,2,4]triazol-1-yl-phenyl)-amine, C16H14N4O
- The crystal structure of (Z)-2-(4-(4-bromophenyl)thiazol-2-yl)-4-(3-hydroxybut-2-enoyl)-5-methyl -1,2-dihydro-3H-pyrazol-3-one – methanol (1/1), C18H18N3O4S
- Crystal structure of tetraaqua-tris(nitrato-κ2 O,O′) erbium(III) monohydrate, Er(NO3)3·5H2O, H10ErN3O14
- The crystal structure of 1-methyl-2-nitro-1H-imidazole 3-oxide, C4H5N3O3
- The crystal structure of 1-methyl-2-nitroimidazole, C4H5N3O2
- The crystal structure of 2-carboxyl-4-nitroimidazole monohydrate, C4H5N3O5
- Crystal structure of bis[hydrido-hexaphenylcarbodiphosphoran][tetra-trifluoromethyl-(μ-diiodo)-diplatinat]
- The crystal structure of poly[μ2-aqua- aqua-(μ3-(E)-2-(4-((2-carbamothioylhydrazineylidene)methyl)phenoxy)acetato-κ3 O:S:S)sodium(I)], C10H14N3O5SNa
- The twinned crystal structure of [4,4′-bipyridine]-1,1′-diium hexachloridostannate(IV), C10H10N2SnCl6
- The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylate-k2 N,O)copper(II)], C34H24N4O4Cu
- Crystal structure of trans-1,2-bis(pyridinium-4-yl) ethylene bis(2-carboxy-4-bromobenzoate) – water (1/4), C14H14BrNO6
- Crystal structure of poly[diaqua-(μ3-fumarato)-(μ3-maleato)-(μ4-1,2,4,5-tetrakis((1H-1,2,4-triazol-1-yl)methyl)benzene)tetracadmium(II)] dihydrate, C34H32N12O9Cd4
- Crystal structure of a second modification of Pachypodol, C18H16O7
- Crystal structure of methyl 2-(4-(2-(cyclopentyl-amino)-1-(N-(4-methoxyphenyl)-1-methyl-5-phenyl-1-H-pyrazole-3-carboxamido)-2-oxoethyl)phenyl)acetate, C34H36N4O5
- The crystal structure of catena-poly[(m2-4,4′-bipyridine-κ2 N:N)-bis(6-phenylpyridine-2-carboxylato-κ2 N,O) zinc(II)], C34H24N4O4Zn
- The crystal structure of hexaquamagnesium(II) (2,4-bis(nitroimino)-6-oxo-1,3,5-triazinane-1,3-diide), C3H15MgN7O12
- The crystal structure of 7-Bromo-2-(4-chloro-phenyl)-quinoxaline, C14H9BrClN2
- Crystal structure of methyl 4-{[4-(4-cyanobenzamido)phenyl]amino}benzofuro[2,3-d]pyrimidine-6-carboxylate, C26H17N5O4
- The crystal structure of (4SR)-7-(3,4-dichlorobenzyl)-4,8,8-trimethyl-7,8-dihydroimidazo[5,1c][1,2,4]triazine-3,6(2H,4H)-dione, C15H16Cl2N4O2
- Crystal structure of catena-poly[{μ2-3-carboxy-2,3-bis((4-methylbenzoyl)oxy)propanoato-κ2 O:O′}tris(methanol-κ1 O)lanthanum(III)], C63H63LaO27
Artikel in diesem Heft
- Frontmatter
- New Crystal Structures
- Crystal structure of {2,2′-{cyclohexane-1,2-diylbis[(azanylylidene)methylylidene]}bis(2,4-dibromophenolato)-κ4 N,N′,O,O′}copper(II) ─ diethylformamide (1/1), C23H23Br4CuN3O3
- The crystal structure of 2-(2-methyl-6-phenyl-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione, C21H14O3
- Crystal structure of bis((1-methylbenzimidazol-2-yl)methyl)amine, C18H19N5
- Crystal structure of (E)-N′-(1-(2-hydroxy-4-methoxyphenyl)ethylidene) isonicotinohydrazide, C15H15N3O3
- Crystal structure of 2-((4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio)acetonitrile, C15H11N5S
- The crystal structure of 2,2′-((1E,1′E)-hydrazine-1,2-diylidenebis(methaneylylidene))bis(4-chlorophenol), C14H10Cl2N2O2
- Dichlorido-{2,6-bis(4,5-dihydro-1H-pyrazol-3-yl)pyridine-κ3 N,N′,N″}zinc(II), C11H9C12N5Zn
- The crystal structure of dichlorido-(2-((4-phenyl-2H-1,2,3-triazol-2-yl)methyl)pyridine-κ2N,N′)palladium(II), C14H12Cl2N4Pd
- The crystal structure of 1-(N1-benzyl-2-methyl-4-nitro-imidazol-5-yl)-4-(prop-2-yn-1-yl) piperazine, C18H21N5O2
- Crystal structure of (μ4-(1,2,4,5-tetra(1,2,4-triazol-1-ylmethyl)-benzene-κ4N:N1:N2:N3)disilver(I) diperchlorate
- The crystal structure of 1-(2-bromoethane)-4-amine-3,5-dinitropyrazole, C5H6Br1N5O4
- Crystal structure of (E)-1-(4-benzyl-3,5-dioxomorpholin-2-ylidene)ethyl acetate, C15H15N1O5
- The crystal structure of poly[diaqua-(μ2-1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ2N:N′)-bis(μ3-terephthalato-κ3O:O′:O′′)dicadmium(II)], C17H15N6O5Cd
- Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)thiophene-2-carbohydrazide, C13H11ClN2O2S
- The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylato-k2 N,O)cobalt(II)]-monohydrate, C36H26N4O5Co
- Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-3-hydroxybenzo-hydrazide monohydrate, C14H13ClN2O4
- Crystal structure of 1,1′-(methylene)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C42H30N14Ni2S8
- Crystal structure of 1,1′-(1,2-ethanediyl)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S:S)nickel(II), C20H14N6NiS4
- The crystal structure of 1-methyl-1H-pyrazol-2-ium nitrate, C4H7O3N3
- The crystal structure of 4,4′-diselanediylbis(8-(hexyloxy)-3,6-dimethyl-1-(piperidin-1-yl)isoquinoline-7-carbonitrile), C46H60N6O2Se2
- The crystal structure of tris(6-methylpyridin-2-yl)phosphine selenide, C18H18N3PSe
- The crystal structure of 1,2-bis(2,4-dinitro-1H-imidazol-1-yl)ethane ─ acetone (1/1), C11H12N8O9
- Crystal structure of [diaqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N,N′,O,O′]nickel(II)] tetrahydrate, C16H12N4NiO10·4H2O
- The crystal structure of tris(4-methyl-1H-pyrazol-1-yl)methane, C13H16N6
- The crystal structure of 5,6-dichloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H8Cl2N2O2
- Crystal structure of (E)-(2-methoxy-benzylidene)-(4-[1,2,4]triazol-1-yl-phenyl)-amine, C16H14N4O
- The crystal structure of (Z)-2-(4-(4-bromophenyl)thiazol-2-yl)-4-(3-hydroxybut-2-enoyl)-5-methyl -1,2-dihydro-3H-pyrazol-3-one – methanol (1/1), C18H18N3O4S
- Crystal structure of tetraaqua-tris(nitrato-κ2 O,O′) erbium(III) monohydrate, Er(NO3)3·5H2O, H10ErN3O14
- The crystal structure of 1-methyl-2-nitro-1H-imidazole 3-oxide, C4H5N3O3
- The crystal structure of 1-methyl-2-nitroimidazole, C4H5N3O2
- The crystal structure of 2-carboxyl-4-nitroimidazole monohydrate, C4H5N3O5
- Crystal structure of bis[hydrido-hexaphenylcarbodiphosphoran][tetra-trifluoromethyl-(μ-diiodo)-diplatinat]
- The crystal structure of poly[μ2-aqua- aqua-(μ3-(E)-2-(4-((2-carbamothioylhydrazineylidene)methyl)phenoxy)acetato-κ3 O:S:S)sodium(I)], C10H14N3O5SNa
- The twinned crystal structure of [4,4′-bipyridine]-1,1′-diium hexachloridostannate(IV), C10H10N2SnCl6
- The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylate-k2 N,O)copper(II)], C34H24N4O4Cu
- Crystal structure of trans-1,2-bis(pyridinium-4-yl) ethylene bis(2-carboxy-4-bromobenzoate) – water (1/4), C14H14BrNO6
- Crystal structure of poly[diaqua-(μ3-fumarato)-(μ3-maleato)-(μ4-1,2,4,5-tetrakis((1H-1,2,4-triazol-1-yl)methyl)benzene)tetracadmium(II)] dihydrate, C34H32N12O9Cd4
- Crystal structure of a second modification of Pachypodol, C18H16O7
- Crystal structure of methyl 2-(4-(2-(cyclopentyl-amino)-1-(N-(4-methoxyphenyl)-1-methyl-5-phenyl-1-H-pyrazole-3-carboxamido)-2-oxoethyl)phenyl)acetate, C34H36N4O5
- The crystal structure of catena-poly[(m2-4,4′-bipyridine-κ2 N:N)-bis(6-phenylpyridine-2-carboxylato-κ2 N,O) zinc(II)], C34H24N4O4Zn
- The crystal structure of hexaquamagnesium(II) (2,4-bis(nitroimino)-6-oxo-1,3,5-triazinane-1,3-diide), C3H15MgN7O12
- The crystal structure of 7-Bromo-2-(4-chloro-phenyl)-quinoxaline, C14H9BrClN2
- Crystal structure of methyl 4-{[4-(4-cyanobenzamido)phenyl]amino}benzofuro[2,3-d]pyrimidine-6-carboxylate, C26H17N5O4
- The crystal structure of (4SR)-7-(3,4-dichlorobenzyl)-4,8,8-trimethyl-7,8-dihydroimidazo[5,1c][1,2,4]triazine-3,6(2H,4H)-dione, C15H16Cl2N4O2
- Crystal structure of catena-poly[{μ2-3-carboxy-2,3-bis((4-methylbenzoyl)oxy)propanoato-κ2 O:O′}tris(methanol-κ1 O)lanthanum(III)], C63H63LaO27