Home Crystal structure of 3-amino-8-methoxy-1-phenyl-1H-benzo[f]chromene-2-carbonitrile, C21H16N2O2
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Crystal structure of 3-amino-8-methoxy-1-phenyl-1H-benzo[f]chromene-2-carbonitrile, C21H16N2O2

  • Rawda M. Okasha , Abd El-Galil E. Amr EMAIL logo , Ahmed M. El-Agrody , Mohamed A. Al-Omar and Hazem A. Ghabbour
Published/Copyright: April 19, 2017
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 232 Issue 3

Abstract

C21H16N2O2, triclinic, P1̅ (no. 2), a = 8.5971(3) Å, b = 9.8586(3) Å, c = 10.6199(4) Å, α = 95.747(2)°, β = 104.384(2)°, γ = 101.768(2)°, V = 842.69(5) Å3, Z = 2, Rgt(F) = 0.0482, wRref(F2) = 0.1377, T = 293(2).

CCDC no.:: 1511395

The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1

Data collection and handling.

Crystal:Colourless block
Size:0.13 × 0.12 × 0.11 mm
Wavelength:Cu Kα radiation (1.54178 Å)
μ:6.8 cm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
2θmax, completeness:133.4°, >98%
N(hkl)measured, N(hkl)unique, Rint:8461, 2941, 0.062
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1905
N(param)refined:263
Programs:SHELX [25, 26] , Bruker programs [27]
Table 2

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

AtomxyzUiso*/Ueq
O10.83623(18)0.40865(14)0.54328(13)0.0528(4)
O20.3608(2)0.87430(18)0.12590(15)0.0774(6)
N10.9375(3)0.3536(2)0.7395(2)0.0589(6)
N20.8629(3)0.6056(2)0.97655(19)0.0767(7)
C10.7481(2)0.4836(2)0.45874(18)0.0439(5)
C20.7163(3)0.4301(2)0.32587(19)0.0529(6)
H2A0.75030.34820.30040.063*
C30.6361(3)0.4967(2)0.23322(19)0.0535(6)
H3A0.61700.46230.14250.064*
C40.5809(2)0.6164(2)0.27006(18)0.0451(5)
C50.4962(3)0.6851(2)0.17349(19)0.0518(6)
H5A0.47730.65140.08270.062*
C60.4422(3)0.7989(2)0.2102(2)0.0543(6)
C70.4666(3)0.8474(2)0.3442(2)0.0540(6)
H7A0.42500.92500.36930.065*
C80.5494(3)0.7842(2)0.4383(2)0.0488(5)
H8A0.56670.81990.52850.059*
C90.6105(2)0.6666(2)0.40522(17)0.0411(5)
C100.7004(2)0.59975(19)0.50236(17)0.0399(5)
C110.7463(2)0.65795(19)0.64729(17)0.0400(5)
H11A0.64300.66800.67050.048*
C120.8185(2)0.5554(2)0.72769(17)0.0429(5)
C130.8640(2)0.4439(2)0.67517(18)0.0441(5)
C140.8440(3)0.5814(2)0.8652(2)0.0513(6)
C150.8674(2)0.80160(19)0.68330(18)0.0416(5)
C160.8578(3)0.9016(2)0.7802(2)0.0562(6)
H16A0.77040.88310.82070.067*
C170.9744(4)1.0285(2)0.8190(3)0.0724(8)
H17A0.96691.09610.88610.087*
C181.0997(3)1.0564(3)0.7613(3)0.0791(9)
H18A1.17961.14340.78820.095*
C191.1104(3)0.9591(3)0.6644(3)0.0756(8)
H19A1.19750.97920.62390.091*
C200.9949(3)0.8315(2)0.6250(2)0.0572(6)
H20A1.00340.76440.55780.069*
C210.3207(4)0.8236(3)−0.0114(2)0.1002(11)
H21A0.25600.8819−0.06080.150*
H21B0.25570.7263−0.02990.150*
H21C0.42270.8278−0.03790.150*
H2N10.960(4)0.284(3)0.692(3)0.099(10)*
H1N10.983(3)0.377(3)0.836(3)0.091(9)*

Source of material

A mixture of 6-methoxy-2-naphthol (0.01 mol), malononitrile (0.01 mol), benzaldehyde (0.01 mol), absolute ethanol (30 mL) and piperidine (0.5 mL) was heated under reflux for 1 h. After a complete precipitation occurred, the solid product was collected by filtration, washed by methanol and recrystallized from ethanol to give the title compound as colourless crystals (yield 88% M.p.: 510–511 K (Lit. M.p.: 519–520 K [1]).

Experimental details

H atoms were placed in calculated positions and were included in the refinement using the riding model approximation, with Uiso(H) = 1.2Ueq(C). The H atoms of the methyl group were allowed to rotate with a fixed angle around the C—C bond to best fit the experimental electron density (HFIX 137 in the SHELX program suite [25]), with Uiso(H) = 1.5Ueq(C).

Discussion

Benzochromene derivatives represent an important class of compounds in heterocyclic chemistry and medicinal chemistry. In recent years, they have attracted considerable attention due to their antimicrobial [2, 3] , antileishmanial [4], [5], [6], [7], [8], [9], anticancer [10], [11], [12], [13], [14], [15], antiproliferative [22], antioxidant [16], [17], [18], hypertensive [14], antitumor [19], [20], [21] effects and activities, as well as proving potentially useful in the treatment of Alzheimer’s disease [23] and schizophrenia disorder [24].

In the title compound C21H16N2O2, the asymmetric unit contains one independent molecule. Molecules are packed in the crystal structure forming a centrosymmetric dimer classical intermolecular hydrogen bond N1—H1N1⋯N2i. The H⋯A distance is 2.07(3) Å, and the angle is 161(2)°. Symmetry code: (i) − x + 2, − y + 1, − z + 2.

Acknowledgement

The project was financially supported by King Saud University, Vice Deanship of Research Chairs.

References

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Received: 2016-10-27
Accepted: 2016-12-28
Published Online: 2017-4-19
Published in Print: 2017-5-24

©2017 Rawda M. Okasha et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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  53. Crystal structure of catena-poly[dichlorido-(μ-ethane-1,2-diyl-bis-(pyridyl-4-carboxylate-κN:N′)mercury(II)], C15H14Cl2HgN2O4
  54. Crystal structure of methyl 2-acetamido-5-chlorbenzoate, C10H10ClNO3
  55. Crystal structure of tetrakis(μ2-3,3-dimethylacrylato-κ2O,O′)-bis(2-aminopyrimidine-κN) dicopper(II), C28H38Cu2N6O8
  56. Crystal structure of 3-amino-8-methoxy-1-phenyl-1H-benzo[f]chromene-2-carbonitrile, C21H16N2O2
  57. Crystal structure of 4-(2-ammonioethyl)morpholin-4-ium dichloride monohydrate, C6H18Cl2N2O2
  58. Crystal structure of 1-(3-((5-bromo-2-hydroxybenzylidene)amino)phenyl)ethanone O-benzyl oxime, C22H19BrN2O2
  59. Crystal structure of 2-(4-(dimethylamino)-2-fluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol monohydrate, C15H20FN7O2
  60. Crystal structure of 4-bromo-2-(1H-pyrazol-3-yl)phenol, C9H7BrN2O
  61. Crystal structure of 1,2,3,4,5-pentamethyl-1,3-cyclopentadiene, C10H16
https://doi.org/10.1515/ncrs-2016-0338
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of 2,5-diiodo-4-nitro-1H-imidazole hemihydrate, C6H4I4N6O5
  3. Crystal structure of catena-poly[μ2-2,2′-(1,3-phenylene)diacetato-κ4O,O′:O′′,O′′′)-(μ2-1,6-bis(2-methyl-1H-benzo[d]imidazol-1-yl)hexane-κ2N:N′)cadmium(II)], C32H34CdN4O4
  4. Crystal structure of poly[aqua-(2,2′-bipyridine-κN,N′)-(μ4-5,5′-(hexane-1,6-diyl)-bis(oxy)diisophthalato κ8O1,O2:O3,O4:O5,O6:O7,O8)manganese(II)], C21H21MnN2O7
  5. Crystal structure of poly-[(μ2-((1,3-bis(benzimidazol-1-yl)propane-κ2N:N′)(μ2-4-tert-butyl-phthalato-κ2O:O′)cobalt(II)] monohydrate, C29H30CoN4O5
  6. Crystal structure of 2-amino-4-(3,4,5-trimethoxy-phenyl)-5-(oxo-5,6,7,8-tetrahydro-4H-chromene)-3-carbonitrile – ethanol (1/1), C21H26N2O6
  7. Crystal structure of ethyl 1-benzyl-5-phenyl-1H-pyrazole-3-carboxylate, C19H18N2O2
  8. Crystal structure of 2-(1-benzyl-3-phenyl-1H-pyrazol-5-yl)-5-(4-nitrobenzylthio)-1,3,4-oxadiazole, C25H19N5O3S
  9. Structure and photochromism of 1,2-bis[2-methyl-5-(2-chlorophenyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C27H16Cl2F6S2
  10. The crystal structure of the Schiff base (E)-2,6-diisopropyl-N-(pyridin-4-ylmethylene)aniline, C18H22N2
  11. Crystal structure of (E)-2,4-dibromo-6-(((4-methyl-2-nitrophenyl)imino) methyl)phenol, C10H14Br2N2O3
  12. Crystal structure of (bis(2,2′-bipyridine-κ2N,N′))-(3,5-dinitrosalicylato-κ2O,O′)nickel(II), C27H18N6NiO7
  13. Crystal structure of 1-(diethoxy phosphonomethyl) 2-benzoyl-3-chloro-2-cyclohexen-1-ol, C18H24ClO5P
  14. Crystal structure of tetraaqua-bis(1,3-benzimidazol-3-ium-1,3-diacetato-κO)copper(II) hemihydrate, C22H27CuN4O12.50
  15. Crystal structure of 1α,11-dihydroxyeremophil-9-en-8-one, C15H24O3
  16. Crystal structure of 1-ferrocenylsulfonyl-1H-imidazo[4,5-b]pyridine, C16H13FeN3O2S
  17. Crystal structure of bis(μ2-azido-κ2N:N)-dichlorido-bis(μ2-2-(pyridin-2-yl)ethan-1-ol-κ2O,N)dicopper(II), C14H18Cl2Cu2N8O2
  18. Crystal structure of (5,15-cis-bis(2-hydroxy-1-naphthyl)-10-phenyl-20-(4-hydroxyphenyl)-porphyrinato)-(pyridine)-zinc(ii) pyridine solvate, C67H47N7O3Zn
  19. Crystal structure of (μ2-[2,2′-bis(diphenylphosphino)-1,1′-binaphthalene oxide-κ2O,P])-iodido copper(I), C44H32CuIOP2
  20. Crystal structure of 6,8-diphenyl-2-(4-fluorophenyl)-2,3-dihydroquinolin-4(3H)-one, C27H20FNO
  21. Crystal structure of 5,11,17,23-tetra(tert-butyl)-25,26,27,28-tetrahexoxycalix[4]arene, C68H104O4
  22. Crystal structure of N,N′–bis(pyridin-4-ylmethyl)pyrazine-2,3-dicarboxamide dihydrate, C18H20N6O4
  23. Crystal structure of a diaqua-bis(3,5-di(1H-imidazol-1-yl)pyridine-κN)-bis(2-(4-carboxy-phenyl)acetato-κO]manganese(II), C40H36MnN10O10
  24. Crystal structure of 4-(4-hydroxy-3-methoxy-phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid methyl ester, C21H25NO5
  25. Crystal structure of (E)-4,4′-(ethene-1,2-diyl)bis(3-nitrobenzoic acid) 1.5 hydrate, C16H13N2O9.5
  26. Crystal structure of (E)-2-(5-(4-fluorophenyl)-3-(furan-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-5-((4-fluorophenyl)diazenyl)-4-methylthiazole, C23H17F2N5OS
  27. Crystal structure of the co-crystalline adduct 4-((4,4-dimethyl-2,6-dioxocyclohexylidene)methylamino)-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide - acetic acid (1/1), C21H24N4O4S ⋅ C2H4O2
  28. Synthesis and crystal structure of 2-((5-chlorobenzo[c][1,2,5]thiadiazol-4-yl)amino)-4,5-dihydro-1H-imidazol-3-ium tetraphenylborate, C33H29BClN5S
  29. Crystal structure of (4-chlorophenyl)(3-ferrocenyl-5-(trifluoromethyl)-1H-pyrazol-1-yl)methanone, C21H14ClF3FeN2O
  30. Crystal structure of (S)-benzyl 3-(benzylcarba-moyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate, C25H24N2O3
  31. Crystal structure of 5-acetyl-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one, C15H17FN2O4
  32. Crystal structure of 2-(4-fluorophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16FIN2
  33. Crystal structure of methyl 1H-indole-2-carboxylate, C10H9NO2
  34. Crystal structure of 2,3-diphenyl-1-[(dipropylamino)acetyl]-1,3-diazaspiro[4.5]decan-4-one, C28H37N3O2
  35. Crystal structure of 1-(2H-1,3-benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propan-1-one, C13H12N2O3
  36. Crystal structure of 2,9-dibromo-1,10-phenanthroline, C12H6Br2N2
  37. Crystal structure of 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione, C18H20FN3S
  38. Crystal structure of trans-bis((E)-7-oxo-4-(phenyldiazenyl)cyclohepta-1,3,5-trien-1-olato)-κ2O,O′)-bis(pyridine-κN)cobalt(II), C36H28CoN6O4
  39. Crystal structure of 2-(4-methyl-3-phenylthiazol-2(3H)-ylidene)malononitrile, C13H9N3S
  40. Crystal structure of (Z)-3-(adamantan-1-yl)-1-(3-chlorophenyl)-S-benzylisothiourea, C24H27ClN2S
  41. Crystal structure of chlorido{[3-(η5-cyclopenta-dienyl)-2,2,3-trimethyl-1-phenylbutylidene] azanido-κN}[η2(N,O)-N,N-dimethylhydroxylaminato]titanium(IV), C20H27ClN2OTi
  42. Crystal Structure of 1,1′-dimethyl-[4,4′-bipyridine]-1,1′-diium tetrachloridozincate(II), C12H14Cl4N2Zn
  43. Crystal structure of 5-nitro-2-(pyrrolidin-1-yl)benzaldehyde, C11H12N2O3
  44. Crystal structure of 2,3-diphenyl-1-(morpholin-4-ylacetyl)-1,3-diazaspiro[4.5]decan-4-one, C26H31N3O3
  45. Crystal structure of 3,3-dimethyl-3,4-dihydro-1H-benzo[c]chromene-1,6(2H)-dione, C15H14O3
  46. Crystal structure of bis(2-(2-hydroxymethyl)pyridine-κ2N,O)-bis(pivalato-κO)nickel(II), C22H32N2NiO6
  47. Crystal structure of (1,10-phenanthroline-κ2N,N′)-bis(1H-pyrazole-3-carboxylato-κ2N,O)manganese(II) trihydrate, C20H20N6O7Mn
  48. The crystal structure of 3-aminopropan-1-aminium iodide, C3H11N2I
  49. Crystal structure of ethyl 1-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4 carboxylate, C12H12ClN3O2
  50. Crystal structure of 4,4′-((1Z,1′Z)-2,2′-(2,5-diethoxy-1,4-phenylene)bis(ethene-2,1-diyl))dipyridine, C24H24N2O2
  51. Crystal structure of (16S)-12,16-epoxy-11,14-dihydroxy-17(15/16)-abeo-3a,18-cyclo-8,11,13-abietatrien-7-one, C20H24O4
  52. Crystal structure of aquadichlorido(2,4,6-tri-2-pyridyl-1,3,5-triazine-κ3N,N′,N′′)nickel(II) monohydrate, C18H16Cl2N6NiO2
  53. Crystal structure of catena-poly[dichlorido-(μ-ethane-1,2-diyl-bis-(pyridyl-4-carboxylate-κN:N′)mercury(II)], C15H14Cl2HgN2O4
  54. Crystal structure of methyl 2-acetamido-5-chlorbenzoate, C10H10ClNO3
  55. Crystal structure of tetrakis(μ2-3,3-dimethylacrylato-κ2O,O′)-bis(2-aminopyrimidine-κN) dicopper(II), C28H38Cu2N6O8
  56. Crystal structure of 3-amino-8-methoxy-1-phenyl-1H-benzo[f]chromene-2-carbonitrile, C21H16N2O2
  57. Crystal structure of 4-(2-ammonioethyl)morpholin-4-ium dichloride monohydrate, C6H18Cl2N2O2
  58. Crystal structure of 1-(3-((5-bromo-2-hydroxybenzylidene)amino)phenyl)ethanone O-benzyl oxime, C22H19BrN2O2
  59. Crystal structure of 2-(4-(dimethylamino)-2-fluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol monohydrate, C15H20FN7O2
  60. Crystal structure of 4-bromo-2-(1H-pyrazol-3-yl)phenol, C9H7BrN2O
  61. Crystal structure of 1,2,3,4,5-pentamethyl-1,3-cyclopentadiene, C10H16
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