Startseite Naturwissenschaften The crystal structure of (Z)-4-amino-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H17N3O2
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The crystal structure of (Z)-4-amino-N-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H17N3O2

  • Wen-Jin Yao ORCID logo EMAIL logo und Cheng-Liang Feng
Veröffentlicht/Copyright: 4. Januar 2024

Abstract

C16H17N3O2, monoclinic, P21/n (no. 14), a = 9.3503(9) Å, b = 9.1998(8) Å, c = 17.7180(18) Å, β = 97.636(9)°, V = 1510.6(3) Å3, Z = 4, R gt (F) = 0.0564, wR ref (F2) = 0.1439, T = 293 K.

CCDC no.: 2321866

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: 0.42 × 0.35 × 0.32 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.08 mm−1
Diffractometer, scan mode: SuperNova, ω
θmax, completeness: 29.3°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 12,640, 3644, 0.023
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 2520
N(param)refined: 213
Programs: Bruker [1], SHELX [2, 3], Olex2 [4], VESTA [5]
Table 2:

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

Atom x y z Uiso*/Ueq
O1 0.44666 (16) 0.07796 (14) 0.67206 (8) 0.0591 (4)
O2 0.59604 (17) 0.96035 (15) 0.79699 (10) 0.0716 (5)
H2 0.538444 0.997779 0.763677 0.107*
N1 0.3749 (2) 0.4000 (2) 0.35025 (9) 0.0664 (5)
H1A 0.387804 0.327679 0.321164 0.080*
H1B 0.290364 0.435929 0.337134 0.080*
N2 0.44729 (17) 0.31289 (16) 0.71087 (8) 0.0483 (4)
H2A 0.450854 0.403365 0.699054 0.058*
N3 0.44931 (17) 0.27029 (17) 0.78591 (9) 0.0522 (4)
C1 0.3868 (2) 0.3505 (2) 0.42503 (11) 0.0513 (5)
C2 0.3227 (2) 0.4273 (2) 0.47900 (11) 0.0586 (5)
H2B 0.267156 0.508868 0.464263 0.070*
C3 0.3401 (2) 0.3844 (2) 0.55376 (11) 0.0544 (5)
H3 0.296884 0.437722 0.589179 0.065*
C4 0.42180 (19) 0.26212 (19) 0.57730 (10) 0.0459 (4)
C5 0.4843 (2) 0.1850 (2) 0.52302 (11) 0.0534 (5)
H5 0.538261 0.102341 0.537533 0.064*
C6 0.4680 (2) 0.2282 (2) 0.44838 (11) 0.0558 (5)
H6 0.511756 0.175196 0.413043 0.067*
C7 0.43959 (19) 0.20895 (19) 0.65662 (11) 0.0472 (4)
C8 0.4758 (2) 0.3678 (2) 0.83712 (11) 0.0541 (5)
C11 0.50449 (19) 0.52436 (19) 0.82411 (10) 0.0450 (4)
C12 0.39991 (19) 0.6164 (2) 0.78794 (11) 0.0500 (5)
H12 0.309343 0.579232 0.769842 0.060*
C13 0.4272 (2) 0.7624 (2) 0.77815 (11) 0.0502 (5)
H13 0.355465 0.822520 0.753838 0.060*
C14 0.5614 (2) 0.8185 (2) 0.80463 (10) 0.0484 (4)
C15 0.6670 (2) 0.7280 (2) 0.84059 (12) 0.0577 (5)
H15 0.757783 0.765197 0.858278 0.069*
C16 0.6385 (2) 0.5831 (2) 0.85035 (11) 0.0563 (5)
H16 0.710330 0.523401 0.874978 0.068*
C9Aa 0.4673 (14) 0.3328 (11) 0.9212 (7) 0.079 (3)
H9AAa 0.561554 0.348466 0.950112 0.095*
H9ABa 0.400556 0.400070 0.940157 0.095*
C10Aa 0.4199 (5) 0.1811 (5) 0.9348 (2) 0.0876 (18)
H10Aa 0.320249 0.169805 0.914160 0.131*
H10Ba 0.431344 0.162220 0.988558 0.131*
H10Ca 0.477524 0.113827 0.910472 0.131*
C9Bb 0.495 (2) 0.298 (2) 0.9138 (12) 0.064 (4)
H9BAb 0.579656 0.335911 0.945308 0.077*
H9BBb 0.505713 0.193049 0.909413 0.077*
C10Bb 0.3583 (13) 0.3355 (13) 0.9469 (5) 0.125 (4)
H10Db 0.277071 0.290959 0.916749 0.188*
H10Eb 0.345865 0.439044 0.946506 0.188*
H10Fb 0.365351 0.300351 0.998257 0.188*
  1. aOccupancy: 0.635 (7), boccupancy: 0.365 (7).

1 Source of materials

A 50 mL round-bottom flask, equipped with a stir bar and rubber septum, was utilized for the experiment. 75 mg of 4-aminobenzohydrazide (0.5 mmol) and 75 mg of 4-hydroxypropiophenone (0.5 mmol) were combined with 25 mL of absolute alcohol in the flask. Following that, 3 drops of glacial acetic acid were added, and the resulting solution was stirred at room temperature for 20 min. The stirring was then continued for additional 5 h at 80 °C. Afterward, the solvent was evaporated using a rotary evaporator to obtain the crude product. Subsequently, the crude product was dissolved in a minimal amount of hot ethanol under controlled heating conditions, and the solution was gradually cooled to room temperature. During this cooling process, a single crystal was observed. The single crystal of the title compound was obtained after 5 days through slow solvent volatilization at room temperature.

2 Experimental details

The single crystal X-ray diffraction experiment utilized a Bruker APEX-II CCD [1]. SHELXT [2] and SHELXL [3] software packages were employed to solve and refine the crystal structure. The OLEX2 [4] and VESTA [5] software packages were utilized for the visualization of the crystal structure.

3 Comment

The acylated derivatives of hydrazine exhibit various biological activities, such as antibacterial, antifungal, insecticidal, and anticonvulsant properties. Additionally, they serve as crucial raw materials for pharmaceutical products, surfactants, and various derivatives [6]. Among them, benzoyl hydrazine derivatives have been extensively studied due to their wide range of biological activities. Multiple crystal structures of these compounds have been reported [7], [8], [9], [10], [11]. Previous studies on their single crystal structures have revealed the presence of different conformations around the C=N double bond, as well as the occurrence of intermolecular hydrogen bonding and ππ interactions [12], [13], [14], [15], [16].

The crystal structure of (Z)-4-amino–N′-(1-(4-hydroxyphenyl)propylidene) benzohydrazide exhibits a Z-type conformation. The 4-aminophenylformamide group and 4-hydroxyphenyl group are located on the same side of the C=N double bond. The two benzene rings undergo significant torsion, with an almost perpendicular arrangement.

Two prominent hydrogen bonds, O2–H2⋯O1 and N1–H1B⋯O2, are formed between the molecules. The bond angle for O2–H2⋯O1 is measured at 164.90(14) degrees, with a bond length of 1.8829(14) Å. The bond angle for N1–H1B⋯O2 is measured at 173.33(13)°, with a bond length of 2.0915(16) Å. The nearly 180° bond angles and relatively short bond lengths suggest strong bonding capability. The two benzene rings in the molecule exhibit ππ interactions, with a certain degree of overlap perpendicular to the (110) crystal plane. These hydrogen bonding and ππ interactions play a significant role in stabilizing the crystal structure [17], [18], [19], [20], [21], [22].


Corresponding author: Wen-Jin Yao, Jiangsu College of Engineering and Technology, Nantong, Jiangsu, China, E-mail:

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: None declared.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2023-11-22
Accepted: 2023-12-26
Published Online: 2024-01-04
Published in Print: 2024-04-25

© 2023 the author(s), published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. Solvothermal synthesis and crystal structure of aqua-tris(p-acetamidobenzoate-κ2O,O′)-(2,2′-bipyridine-κ2N,N′)terbium(III) - water - methanol (1/1/1)
  4. Crystal structure of hexaaquazinc(II) catena-poly[bis(1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine-3-carboxylato-κ2O,O′)-bis(μ2-1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine-3-carboxylato-κ2O:O′)trizinc(II)] hexahydrate C26H36N4O20Zn2
  5. The crystal structure of valinyl-N-ium-4-(5-(thiophen-2-yl)isoxazol-3-yl)phenyl trifluoroacetate
  6. Crystal structure of bis(3,5-diisopropyl-1H-pyrazol-4-ammonium) tetrafluoroterephthalate, 2[C9H18N3][C8F4O4]
  7. Crystal structure of aqua-octakis(μ3-salicylato)-(1,10-phenanthroline)-(acetonitrile)-dicobalt(II)-trititanium(IV), C70H45N3O25Co2Ti3
  8. Crystal structure of catena-poly[aqua-(μ2-4,4′-diimidazole diphenyl ether-κ2N:N′)-(sulfato-κ1O)-cobalt(II)] – dimethylformamide (2/1), C39H37CoN9O8S
  9. Crystal structure of (5R,8R,9R,10R,12R, 13R,14R,17S)-2-(E-3-fluorobenzylidene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl) hexadecahydro-3H-cyclopenta[a]phenanthren-3-one, C37H53FO3
  10. Crystal structure of (Z)-4-((4,5,6-trimethoxy-3-oxobenzofuran-2(3H)-ylidene)methyl)phenyl diphenylphosphinate, C30H25O7P
  11. Crystal structure of 3-((5-methylpyridin-2-yl)amino)-1-phenylpropan-1-one, C15H16N2O
  12. The crystal structure of (R)-9-(5-methoxy-2-methyl-2,3-dihydro-1H-cyclopenta[a]naphthalen-1-ylidene)-9H-thioxanthene, C28H22OS
  13. Crystal structure of diaqua-bis[1-(1-(hydroxymethyl)-1H-pyrazol-3-yl)-5-methyl-1H-1,2,3-triazole-4-carboxylato-κ2N,O)] manganese(II), C16H20MnN10O8
  14. The crystal structure of t-butyl 7-[4-(4-fluorophenyl)-2-[(methanesulfonyl)(methyl)amino]-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoate, C26H36FN3O6S
  15. The crystal structure of samarium sulfate pentahydrate, Sm2(SO4)3(H2O)5
  16. The crystal structure of [triaqua-(8-carboxymethoxy-quinoline-2-carboxylate-κ 4 N,O,O,O)-zinc(II)] monohydrate, C12H15NO9Zn
  17. The crystal structure of 2,3-difluoro-11H-benzo-[4,5]imidazo[2,1-a]isoindol-11-one, C14H6F2N2O
  18. The crystal structure of 2,3-di(9H-carbazol-9-yl)-9H-fluoren-9-one, C37H22N2O
  19. The crystal structure of 5-(2-chloro-3-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)-10,11-dihydro-5H-dibenzo[b,f]azepine, C40H39ClN2
  20. Crystal structure of 2-bromo-1-hydroxy-3-(3-methylbut-2-enyloxy)-9H-xanthen-9-one, C18H15BrO4
  21. Crystal structure of bis(μ2-benzenesulfonato-κ2O:O′)-bis(μ2-6,6′-((ethane-1,2-diylbis(azaneylylidene))bis(methaneylylidene))-bis(2-methoxyphenolato-κ6O,O′:O′,N,N′,O′′:O′′,O′′′))disodium(I)dicopper(II)
  22. The crystal structure of (E)-1,2-bis(benzo[e][1,2]azaborinin-2(1H)-yl)ethene, C18H16B2N2
  23. Crystal structure of 3-oxo-urs-12-en-28-benzyl ester, C37H52O3
  24. The crystal structure of ethyl (E)-1-chloro-3-(4-chloro-1-methyl-1H-indole-2-carbonyl)-4-oxo-2-phenylcyclooct-2-ene-1-carboxylate, C27H25Cl2NO4
  25. The crystal structure of 4,4′-((5-bromo-2-iodo-1,3-phenylene)bis(oxy))bis(tert-butylbenzene) ─ ethanol (2/1), C26H28BrIO2
  26. Crystal structure of (E)-1-(4-(benzyloxy)-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one, C18H19NO3
  27. The crystal structure of N1,N3-bis(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)\ propanediamide hydrate, C25H26N6O4, 2(H2O)
  28. The crystal structure of 2,5-bis[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)amino]cyclohexa-2,5-diene-1,4-dione, C28H26N6O4
  29. Crystal structure of 3,4-bis[2-(hydroxymethyl)-pyrrolidin-1-yl] cyclobut-3-ene-1,2-dione hydrate, C14H22N2O5
  30. The crystal structure of 2-(3,4–dichlorobenzyl)-1H-benzimidazole, C14H10Cl2N2
  31. The crystal structure of 2-(2-((4,6-dimethoxypyrimidin-2-yl)oxy)phenyl)-4-(piperidin-1-yl)-5H-chromeno[2,3-d]pyrimidine, C28H27N5O4
  32. The crystal structure of 6-(benzofuran-2-yl)-2-oxo-4,5-diphenyl-3,4-dihydro-2H-pyran-3-carbonitrile, C26H17NO3
  33. Crystal structure of N-(4-bromobenzyl)-3-(difluoromethyl)-1-methyl-N-(pyridin-2-yl)-1H-pyrazole-4-carboxamide, C18H15BrF2N4O
  34. The crystal structure of the host-guest complex: N-{5-[2-(2,6-dimethylphenoxy)acetamido]-4-hydroxy-1,6-diphenylhexan-2-yl}-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide-diethyl ether (2/1)
  35. The crystal structure of (Z)-4-amino-N-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H17N3O2
  36. The crystal structure of diethyl 1,4-dihydro-2,6-dimethyl-4-(3-cyanophenyl)-3,5-pyridinedicarboxylate, C20H22N2O4
  37. Crystal structure of 3-(5-((4-(difluoromethoxy)phenyl) sulfonyl)-3,4,5,6-tetrahydropyrrolo[3,4-c]pyrrol-2(1H)-yl) oxetane-3-carboxamide, C17H19F2N3O5S
  38. Crystal structure of 2-((2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)amino)-N-(2-(4-methylpiperazin-1-yl)ethyl)benzamide hydrate, C25H37Cl2N5O6
  39. Crystal structure of 3-(benzo[d]thiazol-2-yl)-5-bromo-2-hydroxybenzaldehyde, C14H8BrNO2S
  40. Crystal structure of 3-(difluoromethyl)-1-methyl-N-(pyridin-2-yl)-1H-pyrazole-4-carboxamide, C11H10F2N4O
  41. Crystal structure of 3-(2-ethoxy-2-oxoethyl)-1-isopropyl-1H-imidazol-3-ium hexafluoridophosphate(V), C20H34F12N4P2
  42. Crystal structure of ethyl 5,6-dichloro-2-methyl-2,3-dihydro-1 H-benzo[d]imidazole-2-carboxylate, C11H12Cl2N2O2
  43. The crystal of structure of (OC-6-22)-pentakis(acetonitrile)bromidoruthenium(II)bromide monohydrate, C10H15Br2N5Ru
  44. Crystal structure of (2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(((4aS,5R,6S)-1-oxo-5-vinyl-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl)oxy)tetrahydro-2H-pyran-3-yl 2,3-dihydroxybenzoate hydrate, C23H26O12·H2O
  45. The crystal structure of (E)-4-amino-N′-(1-(4-fluorophenyl)propylidene)benzohydrazide, C16H16FN3O
  46. The crystal structure of 2′-(9H-carbazol-9-yl)-[1,1′-binaphthalen]-2-amine, C32H22N2
  47. Crystal structure of poly[μ3-diiodido-[μ2-di(1H-pyrazol-1-yl)methane-κ2N,N′)]dicopper(I)], C7H8Cu2I2N4
  48. Crystal structure of 3-amino-N′-hydroxy-1H-pyrazole-4-carboximidamide, C4H7N5O
  49. The crystal structure of 1,3-diacetyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, C8H10O4N4
  50. Crystal structure of catena-poly[aqua-(μ2-1,4-diazabicyclo[2.2.2]octane-k2N: N′)-bis(sorbato-κ1O)-copper(II), C18H28CuN2O5
  51. Crystal structure of catena-poly[triaqua-(μ2 -1-(4-carboxylatophenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylato-κ3O,O′:O′′)manganese(II)], C12H12N2O8Mn
  52. The crystal structure of [hexaaquamagnesium(II)] 4-[(pyridine-4-carbonyl)-amino]-phthalate trihydrate, C14H26N2O14Mg
  53. Crystal structure of 1-(p-tolylphenyl)-4-(2-furoyl)-3-methyl-1H-pyrazol-5-ol, C16H14N2O3
  54. The crystal structure of bis(1,4,7,10,13-pentaoxacyclopentadecane)-potassium(I) dichloridocopper(I), C20H40Cl2CuKO10
  55. The crystal structure of tris(tetra-n-butylammonium) hexanitrato-κ2O,O′-lanthanium(III) C48H108N9O18La
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