Home The crystal structure of N′-(tert-butyl)-N′-(3,5-dimethylbenzoyl)-3-methoxy-N,2-dimethylbenzohydrazide, C23H30N2O3
Article Open Access

The crystal structure of N′-(tert-butyl)-N′-(3,5-dimethylbenzoyl)-3-methoxy-N,2-dimethylbenzohydrazide, C23H30N2O3

  • Jiangyu Zheng ORCID logo , Wenhao Tang and Haiyu Pan EMAIL logo
Published/Copyright: August 2, 2024

Abstract

C23H30N2O3, monoclinic, P21/c (no. 14), a = 15.4357(14) Å, b = 7.2340(7) Å, c = 21.8274(17) Å, β = 114.881(5), V = 2211.1(3) Å3, Z = 4, Rgt (F) = 0.0492, wRref (F 2) = 0.1284, T = 293 K.

CCDC no.: 2372792

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: 0.25 × 0.23 × 0.20 mm
Wavelength:

μ:
Mo Kα radiation (0.71073 Å)

0.08 mm−1
Diffractometer, scan mode:

θ max, completeness:
Bruker APEX-II, φ and ω

25.0°, >99 %
N(hkl)measured, N(hkl)unique, R int: 10820, 3889, 0.025
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 2930
N(param)refined: 261
Programs: Bruker, 1 Olex2, 2 SHELX 3 , 4
Table 2:

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

Atom x y z U iso*/U eq
H4A −0.020602 0.672294 0.698823 0.062*
H5A 0.122340 0.692779 0.793352 0.068*
H6A 0.234369 0.461617 0.817913 0.059*
H7A 0.098923 0.026114 0.654459 0.096*
H7B 0.042991 0.152634 0.591854 0.096*
H7C −0.010442 0.062275 0.631512 0.096*
H8A −0.165543 0.573920 0.623102 0.118*
H8B −0.196097 0.520175 0.547252 0.118*
H8C −0.112998 0.661931 0.582423 0.118*
H10A 0.290686 0.365806 0.692414 0.073*
H10B 0.397548 0.301601 0.726583 0.073*
H10C 0.356701 0.429954 0.766025 0.073*
H12A 0.342639 −0.129446 0.885253 0.124*
H12B 0.444174 −0.132758 0.945697 0.124*
H12C 0.424651 −0.247160 0.880189 0.124*
H13A 0.560851 −0.092759 0.870214 0.089*
H13B 0.582105 0.041672 0.931195 0.089*
H13C 0.560599 0.121546 0.859473 0.089*
H14A 0.433251 0.313880 0.873584 0.154*
H14B 0.455673 0.216087 0.942713 0.154*
H14C 0.351454 0.214179 0.885480 0.154*
H17A 0.409504 0.050303 0.651001 0.051*
H19A 0.181957 −0.148430 0.495130 0.058*
H21A 0.222310 −0.272749 0.683392 0.048*
H22A 0.303257 −0.001109 0.472552 0.117*
H22B 0.401533 0.045330 0.532556 0.117*
H22C 0.316675 0.186060 0.511706 0.117*
H23A 0.105250 −0.448821 0.585853 0.118*
H23B 0.082274 −0.380513 0.512469 0.118*
H23C 0.044800 −0.268872 0.557988 0.118*
C1 0.15737 (12) 0.2968 (2) 0.73825 (9) 0.0377 (4)
C2 0.07154 (13) 0.2812 (3) 0.68104 (9) 0.0401 (4)
C3 0.00594 (14) 0.4270 (3) 0.66702 (9) 0.0448 (5)
C4 0.02441 (15) 0.5784 (3) 0.70871 (11) 0.0519 (5)
C5 0.10978 (15) 0.5904 (3) 0.76515 (12) 0.0563 (6)
C6 0.17649 (14) 0.4520 (3) 0.78004 (11) 0.0494 (5)
C7 0.04870 (17) 0.1157 (3) 0.63564 (11) 0.0643 (6)
C8 −0.14312 (18) 0.5521 (4) 0.58884 (13) 0.0784 (8)
C9 0.22626 (12) 0.1386 (2) 0.76037 (8) 0.0350 (4)
C10 0.34218 (14) 0.3301 (3) 0.73426 (10) 0.0484 (5)
C11 0.43968 (14) 0.0313 (3) 0.86724 (9) 0.0519 (5)
C12 0.41002 (18) −0.1350 (4) 0.89741 (11) 0.0828 (9)
C13 0.54556 (14) 0.0248 (3) 0.88353 (10) 0.0596 (6)
C14 0.4180 (2) 0.2104 (5) 0.89480 (12) 0.1027 (12)
C15 0.38713 (12) −0.1133 (2) 0.75285 (8) 0.0359 (4)
C16 0.32404 (12) −0.1077 (2) 0.67837 (8) 0.0347 (4)
C17 0.35367 (13) −0.0193 (3) 0.63419 (9) 0.0426 (4)
C18 0.30033 (14) −0.0342 (3) 0.56485 (9) 0.0469 (5)
C19 0.21797 (14) −0.1382 (3) 0.54148 (9) 0.0487 (5)
C20 0.18685 (13) −0.2284 (3) 0.58463 (9) 0.0460 (5)
C21 0.24143 (13) −0.2124 (3) 0.65352 (9) 0.0397 (4)
C22 0.3335 (2) 0.0574 (4) 0.51592 (11) 0.0782 (8)
C23 0.09660 (17) −0.3420 (4) 0.55780 (11) 0.0784 (8)
N1 0.31417 (10) 0.16738 (19) 0.76127 (7) 0.0347 (3)
N2 0.38365 (10) 0.0310 (2) 0.79140 (7) 0.0376 (4)
O1 0.20613 (9) −0.00672 (18) 0.77963 (7) 0.0503 (4)
O2 0.44035 (10) −0.24500 (18) 0.77644 (7) 0.0562 (4)
O3 −0.07596 (10) 0.4043 (2) 0.60924 (7) 0.0637 (4)

1 Source of materials

In a 100 mL round-bottom flask N′-(tert-butyl)-N′-(3,5-dimethylbenzoyl)-3-methoxy-2-methylbenzohydrazide (500 mg; 1.36 mmol, CH3I (193 mg; 1.36 mmol), K2CO3 (123 mg; 0.89 mmol) and DMF (50 mL) were thoroughly dissolved and mixed, stirred and refluxed at 150 °C in nitrogen atmosphere for 2.5 h, 200 mL of saline was added to the reaction solution cooled to room temperature, and the aqueous layer was extracted with ethyl acetate (50 ml × 3), dry the organic phase with anhydrous sodium sulfate, filtered, and concentrated under reduced-pressure. Methanol is used to recrystallize to obtain the desired compound (white solid, 364 mg, 70 %). Single crystals were obtained by crystallization from a mixture of dichloromethane (1 mL) and n-hexane(2 mL).

2 Experimental details

Using Olex2, 2 the structure was solved with the SHELXT 3 program and refined with the SHELXL 4 package. All hydrogen atoms were placed in the calculated positions.

3 Comment

Hydrazide compounds have been widely used and studied as insect growth regulators. One of the most representative is methoxyfenozide. 5 , 6 , 7 , 8 , 9 Based on the original compound, methoxyfenozide, we synthesized the new compound described in this paper with moderate yields. The introduction of the N1 methyl group has caused some significant changes in the properties of methoxyfenozide itself. The reaction route adopted in this paper has good substrate applicability and functional group compatibility, which provides a convenient and efficient reaction route for the introduction of different substitutes at the N1 position of methoxyfenozide.

The molecule in the title compound adopts a non-planar conformation, with two aromatic rings located in different planes, separated by a dihedral angle of 92.9°. In the crystal structure, there are two carbonyl groups and one nitrogen-nitrogen single bond, and the two carbonyl groups are connected by a nitrogen-nitrogen single bond, and the length of the nitrogen-nitrogen single bond of N(1)–N(2) is 1.401(19) Å. 10 The similar structures that have been published remain structurally stable by O–H⃛O hydrogen bond, the molecules are assembled by the intermolecular interactions among the benzene rings and dimethylbenzene units and CH⋅⋅⋅O hydrogen bonds between the acyl oxygen atom and the methoxy group into two-dimensional (2D) supramolecular layers.


Corresponding author: Haiyu Pan, College of Pharmacy, North China University of Science and Technology, Tangshan, Hebei 063000, P.R. China, Email:

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

  2. Competing interests: The authors declare no conflicts of interest regarding this article.

References

1. SAINT. Program for Data Extraction and Reduction; Bruker AXS, Inc: Madison, WI, 2001.Search in Google Scholar

2. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. Olex2: A Complete Structure Solution, Refinement and Analysis Program. J. Appl. Cryst. 2009, 42, 339–341; https://doi.org/10.1107/s0021889808042726.Search in Google Scholar

3. Sheldrick, G. M. Shelxtl – Integrated Space-Group and Crystal-Structure Determination. Acta Crystallogr. 2015, A71, 3–8.10.1107/S2053273314026370Search in Google Scholar PubMed PubMed Central

4. Sheldrick, G. M. Crystal Structure Refinement with Shelxl. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Search in Google Scholar

5. Wang, J.; Tian, D. Study on the Sublethal Effect of Methoxyfenozide on Spodoptera Litura. Cotton Science 2009, 21, 6.Search in Google Scholar

6. Schaefer, S.; Ledermann, N. Dihydrazides as Fragrance or Repellent Precursor Compounds: DE201910125274[P]. DE102019125274A1[2024–02–21].Search in Google Scholar

7. Shengde, W. Research Progress of Acylhydrazine in Insect Growth Regulator. Guangdong Chemical Industry 2004, 5, 37–41.Search in Google Scholar

8. Yan, J., Liao, Y., Yan, S., Cao, C., Feng, C. Effect of Methoxyfenozide on the Activities of Detoxification Enzymes and Protective Enzymes in Gypsy Moth. J. Northeast For. Univ. 2010, 038, 112–114.Search in Google Scholar

9. Chang, J.; Liu, Y.; Zhang, T.; Chen, Z.; Fang, H.; Hua, X. A Comprehensive Investigation of Hydrazide and its Derived Structures in the Agricultural Fungicidal Field. J. Agric. Food Chem. 2023, 71, 8297–8316; https://doi.org/10.1021/acs.jafc.3c00786.Search in Google Scholar PubMed

10. Wang, Y.; Wang, C.; Gao, X.; Liu, B. The Crystal Structure of (E)-4- Chloro-N′-(1-(4-Hydroxyphenyl)propylidene)benzohydrazide, C16H15ClN2O2. Z. Kristallogr. N. Cryst. Struct. 2024, 239, 103–104; https://doi.org/10.1515/ncrs-2023-0458.Search in Google Scholar

Received: 2024-04-14
Accepted: 2024-07-23
Published Online: 2024-08-02
Published in Print: 2024-10-28

© 2024 the author(s), published by De Gruyter, Berlin/Boston

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

Articles in the same Issue

  1. Frontmatter
  2. Editorial
  3. Editorial 2024 – New developments and changes of Zeitschrift für Kristallographie – New Crystal Structures
  4. New Crystal Structures
  5. Hydrogen bonding and π⋅⋅⋅halogen interactions in the crystal structure of bis(theophyllinium) hexachloridoplatinate(IV) monohydrate
  6. The crystal structure of 6-amino-2-carboxypyridin-1-ium perchlorate, C6H7ClN2O6
  7. Crystal structure of poly[(μ4-(3-amino-1H-1,2,4-triazol-1-yl)benzene-1,3-dicarboxylato-κ 4 N:O:O':O')(1-methylpyrroldin-2-one-κ1O)dicopper(II)] – 1-methylpyrroldin-2-one (1/3), C40H48Cu2N12O12
  8. The crystal structure of 18-crown-6-k6O6(2,4,5-trinitroimidazol-1-ido-k1O)potassium(I)
  9. Crystal structure of poly[tetraaqua-bis(μ2-5-bromoisophthalato-κ3O,O:O)-(μ2-1,5-bis(imidazol-2-methyl)pentane-κ2N:N)dicadmium(II)] dihydrate
  10. Crystal structure of (5R,6S,E)-5-acetoxy-2-methyl-6-((2aR,3R,5aS,5bS,11aR,12aS)-2a,5a,8,8-tetramethyl-9-oxotetradecahydro-1H,12H-cyclopenta[a]cyclopropa[e]phenanthren-3-yl)hept-2-enoic acid, C32H48O5
  11. The crystal structure of poly[diaqua-bis(μ2 -thiocyanato-κ2N:O)cobalt(II) monohydrate
  12. The crystal structure of 1,3,5-tri(1H-imidazol-1-yl)benzene–2,3,5,6-tetrachlorobenzene-1,4-dicarboxylic acid (1/1)
  13. Crystal structure of dichlorido-bis(1-[(2-ethyl-benzimidazole-1-yl)methyl]-1H–benzotriazole) cadmium(II), C32H32CdN10OCl2
  14. The crystal structure of N′-(tert-butyl)-N′-(3,5-dimethylbenzoyl)-3-methoxy-N,2-dimethylbenzohydrazide, C23H30N2O3
  15. Crystal stucture of 3-benzamido-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluorobenzamide
  16. Crystal structure of bis(μ-benzeneselenolato)-(tetracarbonyl)-{μ-[N-(diphenylphosphanyl)-N-(3-ethynylphenyl)-P,P-diphenylphosphinous amide]} diiron, C48H35Fe2NO4P2Se2
  17. The crystal structure of 2′-(p-tolyl)-4′H-spiro[isochromane-1,1′-naphthalene]-3,4′-dione, C25H18O3
  18. The crystal structure of poly[hexaqua-tetrakis(μ4-pyridine-2,4-dicarboxylate-κ5N: O: O′: O″: O‴)-bi(μ2-pyridine-2,4-dicarboxylate-κ3N: O: O′)-digadolinium(III)tricopper (II)], [Gd2Cu3(C7H3NO4)6(H2O)6] n
  19. Crystal structure of poly[bis(4-(4-(pyridin-4-yl)phenyl)pyridin-1-ium-κ1N)-(μ4-benzene-1,2,4,5-tetracarboxylato-κ5O:O′: O″:O‴:O⁗)-(μ2-2,5-dicarboxyterephthalato-κ2O:O′)dizinc(II)], C52H32N4O16Zn2
  20. The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 2-carboxy-6-nitrobenzoate monohydrate, C24H25FN4O10
  21. Crystal structure of dichlorido-(1-((3,5-dimethyl-2,3-dihydro-1H-1,2,3-triazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-k1N)zinc(II), C22H24ZnN12Cl2
  22. The crystal structure of (3-chlorothiophene-2-carboxylato-κ2O, O′)-(2,2′-dipyridyl-κ2N,N′)lead(II), C20H12Cl2N2O4S2Pb
  23. Synthesis and crystal structure of (Z)-4-((1-(3-fluorophenyl)-1H-1,2,3-triazol-4-yl)methylene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, C19H14FN5O
  24. The crystal structure of the coordination compound catena-poly[(18-crown-6-ether-κ6O6)(4,5-dinitroimidazolato-κ1O)potassium(I)]
  25. Crystal structure of 7-(diethylamino)-3-(trifluoroacetyl)-2H-chromen-2-one, C15H14F3NO3
  26. Crystal structure of dichlorido-1-[(2-ethylimidazole-1-yl)methyl]-1H–benzotriazole κ1N zinc(II), C24H26ZnN10Cl2
  27. Crystal and molecular structure of 5-bromopyridine-2,3-diamine
  28. Crystal structure of catena-poly[bis(μ2-1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine-3-carboxylato-k3-O,O:O)hexaqua-dicobalt tetrahydrate], C26H36N4O20Co2
  29. Crystal structure of thiocyanate-κ1N-bis(μ1-2,6-diformyl-4-methylphenol oxime-κ2N,O)-manganese(III) acetonitrile solvate, C21H21MnN6O6S
  30. The crystal structure of pyrrolidin-1-yl pivalate, C9H13NO4
  31. The crystal structure of 2,2′-(2,2-diphenylethene-1,1-diyl)bis(1,4-dimethoxybenzene), C30H28O4
  32. Crystal structure of bis(benzyltrimethylammonium) tetrathiotungstate(VI), {(C6H5CH2)(CH3)3N}2[WS4]
  33. The crystal structure of ethyl (Z)-2-(ethoxymethylene)-3-oxobutanoate, C9H14O4
  34. The crystal structure of (E)-6-bromo-3,5-dimethyl-2-(1-phenylprop-1-en-2-yl)-3Himidazo[4,5b]pyridine, C17H16BrN3
  35. Crystal structure of (3S,3′S,4R,4′S)-3′-(furan-3-yl)-3-hydroxy-4′-methyl-3,5,6′,7′-tetrahydro-1H,3′H-4,5′-spirobi[isobenzofuran]-1,1′(4′H)-dione-methanol (1/1), C21H22O7
  36. Cocrystal structure of progesterone-isophthalic acid, C25H33O4
  37. The crystal structure of 3-(6-fluoro-1H-indol-3-yl)-1-methylquinoxalin-2(1H)-one, C17H12FN3O
  38. Crystal structure of S-(4-carboxybutyl)- l -cysteine
  39. The cocrystal of 2,2′-(hydrazine-1,1-diyl)bis(1H-imidazole-4,5-dicarbonitrile)– methanol (2/3)
  40. Crystal structure of (1′R,2′S,4′R,6′S)-4,6-dihydroxy-1′,8′,8′-trimethyl-3-(3-methylbutanoyl)-4′,8′,6′,1′,7,2′-hexahydro-1H-4′,6′-methanoxanthene-8-carbaldehyde, C23H30O5
  41. Crystal structure of (3,6-di(2-pyridyl)-4-methylphenyl pyridazine-k 2 N,N′)-bis(1-phenyl-pyrazole-κ 2 C,N) iridium(III) hexafluorophosphate, C39H29F6IrN8P
  42. Crystal structure of 1,5-bis[(E)-1-(2-hydroxyphenyl)ethylidene]thiocarbonohydrazide dimethyl sulfoxide monosolvate, C17H18N4O2S·C2H6OS
  43. Crystal structure of (S)-4-(2-(4-(2-acetyl-5-chlorophenyl)-3-methoxy-6-oxopyridazin-1(6H)-yl)-3-phenylpropanamido)benzoic acid monohydrate, C29H26ClN3O7
  44. The crystal structure of 1,3-bis(2,4-dinitro-1H-imidazol-1-yl)propane
  45. Crystal structure of 4-chlorobenzyl (S)-2-(6-methoxynaphthalen-2-yl)propanoate, C21H19ClO3
  46. Crystal structure of 1-(5-(benzo[d][1,3]dioxol-5-yl)-4-benzyl-1-(4-bromophenyl)-4,5-dihydro-1H-1,2,4-triazol-3-yl)ethan-1-one, C24H20BrN3O3
  47. The crystal structure of (Z)-3′-(2-(1-(3,4-dimethyl-phenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene)hydrazinyl)-2′-hydroxy-[1,1′-biphenyl]-3-carboxylicacid ─ methanol (1/1), C26H26N4O5
  48. Crystal structure of (S)-1-phenylpropan-1-aminium (S)-(1-phenylpropyl)carbamate C19H26N2O2
  49. Synthesis and crystal structure of methyl 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate, C18H16BrN3O2S
  50. The crystal structure of trichlorobis(pyridine-2,6-dithio-κS-carbomethylamido)antimony(III), [SbCl3(C9H11N3S2)2]
  51. Crystal structure of 1,8-dihydroxy-3-{[(triphenylstannyl)oxy]carbonyl} anthracene-9,10-dione, C33H22O6Sn
  52. The crystal structure of (E)-4-(2-(pyridin-4-ylmethylene)hydrazine-1-carbonyl)pyridin-1-ium-2-olate dihydrate, C12H14N4O4
  53. The crystal structure of 6-amino-pyridinium-2-carboxylate, C6H6N2O2
  54. The crystal structure of catena-poly[aqua-nitrato-κ3O,O:O′′-(1,10-phenanthroline-κ2N,N)sodium(I)], C24H18N6O7Na2
  55. Retractions
  56. Retraction of: Crystal structure of bis[diaquaisonicotinatosamarium(III)]-µ-isonicotinato-[diisonicotinatocopper(II)], CuSm2(C6H4NO2)8(H2O)4
  57. Retraction of: Crystal structure of aqua(2,2-bipyridine-k 2 N:N′)(nitrato)-(4-aminobenzoato)cadmium(II) nitrate, [Cd(H2O)(NO3)(C10H8N2)(C7H7NO2)][NO3]
Downloaded on 30.9.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2024-0173/html
Scroll to top button