Home The crystal structure of N′-((1E,2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-ylidene)-3-methylbenzohydrazide, C23H22N2O4
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The crystal structure of N′-((1E,2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-ylidene)-3-methylbenzohydrazide, C23H22N2O4

  • Xiang Yu , You-Fang Zhao , Yan Qin , Jing Yan and Ya-Fang Chen EMAIL logo
Published/Copyright: June 22, 2019

Abstract

C23H22N2O4, monoclinic, P21/c (no. 14), a = 17.7478(4) Å, b = 10.0041(2) Å, c = 24.4749(6) Å, β = 111.111(2)°, V = 4053.88(17) Å3, Z = 8, Rgt(F) = 0.0614, wRref(F2) = 0.1749, T = 290 K.

CCDC no.: 1922778

The asymmetric unit containing two crystallographically independent molecules is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colourless block
Size:0.29 × 0.28 × 0.27 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.09 mm−1
Diffractometer, scan mode:SuperNova, ω
θmax, completeness:28.5°, >99%
N(hkl)measured, N(hkl)unique, Rint:93062, 9585, 0.055
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 6513
N(param)refined:529
Programs:CrysAlisPRO [1], Olex2 [2], SHELX [3], [4]
Table 2:

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

AtomxyzUiso*/Ueq
O10.26905(9)0.96583(15)0.33980(6)0.0499(4)
O20.24264(14)1.1723(2)0.30743(9)0.0881(6)
O30.34233(11)0.54040(16)0.42024(8)0.0645(5)
O40.16120(10)1.24119(13)0.61106(7)0.0517(4)
N10.20741(10)1.05625(16)0.54586(7)0.0422(4)
N20.15460(11)1.03074(16)0.57499(8)0.0448(4)
H20.13410.95220.57310.054*
C10.23379(15)1.0559(3)0.29467(11)0.0613(6)
C20.19009(17)1.0006(3)0.23797(12)0.0736(8)
H2A0.16721.05770.20630.088*
C30.18169(16)0.8688(3)0.22975(11)0.0708(7)
H30.15150.83600.19280.085*
C40.21820(14)0.7768(3)0.27665(10)0.0534(6)
C50.21527(16)0.6387(3)0.27125(12)0.0653(7)
H50.18530.60080.23530.078*
C60.25518(16)0.5564(3)0.31733(12)0.0626(7)
H60.25220.46410.31270.075*
C70.30073(14)0.6131(2)0.37172(10)0.0499(5)
C80.30533(12)0.7516(2)0.37966(9)0.0407(5)
C90.26371(12)0.8292(2)0.33160(9)0.0429(5)
C100.3495(2)0.3997(3)0.41407(17)0.0938(10)
H10A0.37510.38270.38620.141*
H10B0.29680.35980.40060.141*
H10C0.38150.36190.45130.141*
C110.35239(12)0.8148(2)0.43816(9)0.0415(4)
H11A0.39630.75610.46020.050*
H11B0.37550.89860.43190.050*
C120.29926(11)0.84007(19)0.47269(8)0.0379(4)
H120.27560.76500.48220.045*
C130.28159(11)0.95671(19)0.49148(8)0.0380(4)
C140.22740(12)0.9522(2)0.52403(9)0.0402(4)
H140.20640.87000.52920.048*
C150.31369(16)1.0894(2)0.48191(12)0.0609(6)
H15A0.37121.09120.50180.091*
H15B0.28951.15890.49710.091*
H15C0.30101.10310.44070.091*
C160.13491(12)1.12703(19)0.60623(9)0.0398(4)
C170.07825(13)1.08329(19)0.63543(9)0.0439(5)
C180.09078(14)1.1311(2)0.69118(9)0.0458(5)
H180.13411.18790.70940.055*
C190.03929(16)1.0952(2)0.72021(11)0.0569(6)
C20−0.0245(2)1.0119(3)0.69171(15)0.0821(10)
H20−0.05940.98690.71060.099*
C21−0.0380(2)0.9649(3)0.63670(17)0.0982(12)
H21−0.08190.90950.61840.118*
C220.01351(18)0.9998(3)0.60823(14)0.0771(9)
H220.00470.96710.57090.093*
C230.0528(2)1.1483(4)0.78048(13)0.0904(10)
H23A0.10561.18740.79660.136*
H23B0.04861.07640.80520.136*
H23C0.01281.21490.77810.136*
O50.56386(10)0.46774(18)0.70392(8)0.0614(4)
O60.59196(16)0.6733(3)0.73497(13)0.1088(8)
O70.50174(11)0.04222(18)0.62100(9)0.0744(5)
O80.11940(10)0.74961(14)0.56374(9)0.0658(5)
N30.23454(9)0.55897(16)0.58128(7)0.0373(4)
N40.15676(9)0.53398(15)0.57946(7)0.0366(4)
H40.14310.45390.58470.044*
C240.60162(18)0.5575(4)0.74803(15)0.0775(8)
C250.6489(2)0.5020(4)0.80416(15)0.0917(10)
H250.67530.55930.83510.110*
C260.65588(19)0.3688(4)0.81295(13)0.0879(10)
H260.68700.33600.84970.106*
C270.61669(14)0.2782(3)0.76716(11)0.0656(7)
C280.62150(16)0.1388(3)0.77156(13)0.0756(9)
H280.65110.10040.80750.091*
C290.58408(16)0.0571(3)0.72479(14)0.0710(8)
H290.5879−0.03530.72910.085*
C300.54028(13)0.1141(3)0.67072(12)0.0570(6)
C310.53350(12)0.2530(2)0.66384(10)0.0477(5)
C320.57150(13)0.3314(3)0.71235(11)0.0531(6)
C330.5124(2)−0.0993(3)0.62216(19)0.1038(12)
H33A0.4833−0.13540.58400.156*
H33B0.4923−0.13790.65010.156*
H33C0.5688−0.11960.63310.156*
C340.48551(12)0.3149(2)0.60558(10)0.0490(5)
H34A0.51040.39860.60130.059*
H34B0.48600.25560.57430.059*
C350.40024(11)0.3401(2)0.60045(9)0.0419(5)
H350.37100.26590.60440.050*
C360.36113(11)0.45670(19)0.59091(8)0.0370(4)
C370.27756(11)0.45395(19)0.58787(8)0.0370(4)
H370.25460.37200.59090.044*
C380.39748(13)0.5875(2)0.58287(11)0.0551(6)
H38A0.40540.58700.54610.083*
H38B0.44850.59980.61410.083*
H38C0.36170.65920.58320.083*
C390.10250(12)0.63346(19)0.56957(9)0.0388(4)
C400.01956(11)0.59498(19)0.56642(8)0.0365(4)
C410.00208(11)0.4783(2)0.58977(9)0.0390(4)
H410.04330.41740.60740.047*
C42−0.07599(12)0.4500(2)0.58743(9)0.0451(5)
C43−0.13603(12)0.5427(2)0.56054(10)0.0497(5)
H43−0.18830.52640.55910.060*
C44−0.12031(13)0.6574(2)0.53608(10)0.0515(6)
H44−0.16180.71730.51780.062*
C45−0.04303(12)0.6843(2)0.53851(9)0.0456(5)
H45−0.03250.76190.52160.055*
C46−0.09364(15)0.3244(3)0.61374(14)0.0766(8)
H46A−0.09030.24920.59030.115*
H46B−0.14700.32920.61500.115*
H46C−0.05500.31400.65280.115*

Source of material

In a representative experiment 7-methoxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one (1.0 mmol) reacted with SeO2 (1.1 mmol) in dioxane (10 mL) at 80 °C to afford the aldehyde, and then reacted with 4-methylbenzoyl hydrazine (1.0 mmol), and two drops of HOAc in EtOH (10 mL) at 80 °C. Suitable colorless block crystals of this compound were then obtained after recrystallization from methanol.

Experimental details

The structure was solved with the Olex2 program [2] as an interface together with the SHELXT and SHELXL programs [3], [4]. All non-hydrogen atoms were assigned anisotropic displacement parameters in the refinement. Hydrogen atoms were treated using a riding model.

Comment

Coumarins were natural products with diverse bioactivities such as anti-tumor [5], anti-inflammatory [6] and antimicrobial activity [7]. On the other hand, recent studies show that introduction of hydrazone fragments into natural products could displayed the remarkable biological activity [8], [9]. In order to discover more compounds with potential bioactivities we prepared a coumarin-based hydrazone derivative by introduction of hydrazone moiety into the coumarin.

The asymmetric unit of the title structure consists of two crystallographically independent molecules (cf. the figure). Geometric parameters of the title structure are in the usual ranges [10]. The compound contains one methoxy group, one lactone and two methyl-groups. The length of C—C double bond are, longer than the length of C—N double bond. Both of the configuration of the C—C double bond and the configuration C—N double bond are in type E, as well as the similar structure that reported [11].

Acknowledgements

This work was supported by the Science and Technology Fund of Guizhou [No.(2017)5735–22], the Youth Talent Development Project of Guizhou Provincial Department of Education [2017]169, and Special Topics for Scientific and Technological Research on Traditional Chinese Medicine and Ethnic Medicine [QZYY2017–081].

References

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8. Qu, H.; Lv, M.; Yu, X.; Lian, X. H.; Xu, H.: Discovery of some piperine-based phenylsulfonylhydrazone derivatives as potent botanically narcotic agents. Sci. Rep. 5 (2015) 13077.10.1038/srep13077Search in Google Scholar PubMed PubMed Central

9. Yu, X.; Feng, G.; Huang, J. L.; Xu, H.: Evaluation of some quinoline-based hydrazone derivatives as insecticidal agents. RSC Adv. 6 (2016) 30405–30411.10.1039/C6RA00993JSearch in Google Scholar

10. Yu, X.; Qin, Y.; Yan, J.; Chen, Y.-F.: Crystal structure of N′-((1E,2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-ylidene)-4-methylbenzenesulfonohydrazide, C22H22O5N2S. Z. Kristallogr. NCS 234 (2019) 367–368.10.1515/ncrs-2018-0427Search in Google Scholar

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Received: 2019-04-07
Accepted: 2019-06-13
Published Online: 2019-06-22
Published in Print: 2019-09-25

©2019 Xiang Yu et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 Public License.

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  62. Crystal structure of 2-(2-(6-methylpyridin-2-yl)naphthalen-1-yl)pyrimidine, C20H15N3
  63. The crystal structure of N′-((1E,2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-ylidene)-3-methylbenzohydrazide, C23H22N2O4
  64. Crystal structure of catena-poly[(μ2-isophthalato-κ2O:O′)-(2,5-di(pyrazin-2-yl)-4,4′-bipyridine-κ3N,N′,N′′)zinc(II)] — water (2/5), C26H21N6O6.5Zn
  65. Crystal structure of (3E,5E)-3,5-bis(3-nitrobenzylidene)-1-((4-(trifluoromethyl)phenyl)sulfonyl)piperidin-4-one — dichloromethane (2/1), C53H38Cl2F6N6O14S2
  66. Crystal structure of (μ2-oxido)-bis(N,N′-o-phenylenebis(salicylideneiminato))diiron(III) — N,N′-dimethylformamide, C47H43Fe2N4O9
  67. Crystal structure of N1,N3-bis(2-hydroxyethyl)-N1, N1,N3,N3-tetramethylpropane-1,3-diaminium dibromide, C11H28Br2N2O2
  68. Crystal structure of (E)-N-(4-chlorophenyl)-1-(pyridin-2-yl)methanimine, C12H9ClN2
  69. Crystal structure of 8-bromo-6-oxo-2-phenyl-6H-pyrrolo[3,2,1-ij]quinoline-5-carbaldehyde, C18H11BrNO2
  70. Crystal structure of 1,4-bis(2-azidoethyl)piperazine-1,4-diium dichloride trihydrate, C8H18N8Cl2 ⋅ 3 H2O
  71. Crystal structure of (E)-4-bromo-N-(pyridin-2-ylmethylene)aniline, C12H9BrN2
  72. Crystal structure of bis[(2-(3-bromophenyl)-5-methyl-1,3-dioxane-5-carboxylato-κ-O)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II), C40H60Br2N4NiO8
  73. The crystal structure of (1E,2E)-2-methyl-4-((7-oxo-7H-furo[3,2-g]chromen-9-yl)oxy)but-2-enal O-isonicotinoyl oxime–trichloromethane (3/1), C67H49Cl3N6O18
  74. Crystal structure of 3-(2-ethoxy-2-oxoethyl)-1-methyl-1H-imidazol-3-ium hexafluoridophosphate(V), C8H13F6N2O2P
  75. Crystal structure of bis[(2-(2-bromophenyl)-5-ethyl-1,3-dioxane-5-carboxylato-κO)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II) hemihydrate C42H65Br2N4NiO8.5
  76. The crystal structure of N-(7-(4-fluorobenzylidene)-3-(4-fluorophenyl)-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbonothioyl)benzamide, C28H23F2N3OS
  77. The crystal structure of N1,N4-bis(pyridin-3-yl)cyclohexane-1,4-dicarboxamide, C18H20N4O2
  78. Crystal structure of (E)-2-(3,6-bis(ethylamino)-2,7-dimethyl-9H-xanthen-9-yl)-N′-((6-methylpyridin-2-yl)methylene)benzohydrazide – methanol (1/1), C34H37N5O3
  79. Crystal structure of 2-oxo-1-(pyrimidin-5-ylmethyl)-3-(3-(trifluoromethyl)phenyl)-1,2-dihydro-5l4-pyrido[1,2-a]pyrimidin-4-olate, C20H13F3N4O2
  80. Crystal structure of poly[(μ3-9H-carbazole-3,6-dicarboxylato-κ3O1: O2: O3)(μ2-4-(pyridin-4-yl)pyridine-κ2N1:N1′)zinc(II)], C19H11N2O4Zn
  81. Crystal structure of (E)-N′-((1,8-dihydropyren-1-yl)-methylene)picolinohydrazide, C23H15N3O
  82. Crystal structure of catena-poly{[μ2-1,2-bis(diphenylphosphino)ethane]dichloridocadmium(II)}, C26H24CdCl2P2
  83. Crystal structure of the 1:2 co-crystal between N,N′-bis(4-pyridylmethyl)oxalamide and acetic acid as a dihydrate, C14H14N4O2⋅2 C2H4O2⋅2 H2O
  84. Crystal structure of the co-crystal N,N′-bis(3-pyridylmethyl)oxalamide acetic acid (1/2), C14H14N4O2⋅2C2H4O2
  85. Crystal structure of the co-crystal N,N′-bis(4-pyridylmethyl)oxalamide and 2,3,5,6-tetrafluoro-1,4-di-iodobenzene (1/1), C14H14N4O2⋅C6F4I2
  86. Crystal structure of the co-crystal 4-[(4-carboxyphenyl)disulfanyl]benzoic acid–(1E,4E)-1-N,4-N-bis(pyridin-4-ylmethylidene)cyclohexane-1,4-diamine (1/1), C14H10O4S2⋅C18H20N4
  87. Crystal structure of hexacarbonyl-bis(μ2-di-n-propyldithiocarbamato-κ3S,S′:S3S:S:S′)-di-rhenium(I), C20H28N2O6Re2S4
  88. Crystal structure of fac-tricarbonyl-morpholine-κN-(morpholinocarbamodithioato-κ2S,S′)rhenium(I), C12H17N2O5ReS2
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