Startseite The crystal structure of (E)-N ′-(2-bromobenzylidene)-2-naphthohydrazide, C36H26Br2N4O2
Artikel Open Access

The crystal structure of (E)-N -(2-bromobenzylidene)-2-naphthohydrazide, C36H26Br2N4O2

  • Lin Yuan ORCID logo , Shao-Wen Deng , Fang Liu ORCID logo und Zhong-Yan Li EMAIL logo
Veröffentlicht/Copyright: 1. Juni 2023

Abstract

C36H26Br2N4O2, triclinic, P1 (no. 1), a = 8.700(5) Å, b = 9.188(5) Å, c = 9.722(6) Å, α = 91.610(6)°, β = 91.436(6)°, γ = 100.925(6)°, V = 762.4(8) Å3, Z = 1, R g t (F) = 0.0381, w R r e f (F 2) = 0.1016, T = 296(2) K.

CCDC no.: 2263812

The molecular structure 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: block
Size: 0.45 × 0.42 × 0.38 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 2.70 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 25.0°, 99 %
N(hkl)measured , N(hkl)unique, R int: 7133, 5181, 0.021
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 4577
N(param)refined: 397
Programs: Bruker [1], SHELX [2, 3]
Table 2:

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

Atom x y z U iso*/U eq
Br1 −0.79202 (8) −1.54403 (7) 0.77589 (6) 0.0770 (3)
Br2 −0.18486 (7) −0.84277 (7) −0.03225 (7) 0.0745 (3)
C1 −0.6556 (6) −0.9566 (6) 0.2845 (5) 0.0378 (11)
C2 −0.5987 (7) −0.8701 (7) 0.1693 (6) 0.0495 (13)
H2 −0.517986 −0.895443 0.118396 0.059*
C3 −0.6616 (7) −0.7522 (6) 0.1343 (6) 0.0484 (13)
H3A −0.624865 −0.699254 0.057831 0.058*
C4 −0.7811 (6) −0.7072 (6) 0.2103 (6) 0.0432 (12)
C5 −0.8429 (8) −0.5799 (7) 0.1798 (7) 0.0560 (15)
H5 −0.807376 −0.525094 0.104095 0.067*
C6 −0.9528 (8) −0.5363 (7) 0.2587 (8) 0.0634 (17)
H6 −0.990912 −0.451264 0.237722 0.076*
C7 −1.0090 (8) −0.6185 (9) 0.3713 (10) 0.068 (2)
H7 −1.084797 −0.587861 0.424926 0.081*
C8 −0.9538 (7) −0.7444 (8) 0.4042 (8) 0.0566 (17)
H8 −0.993355 −0.798479 0.479220 0.068*
C9 −0.8383 (6) −0.7919 (6) 0.3256 (6) 0.0409 (12)
C10 −0.7725 (6) −0.9160 (6) 0.3587 (5) 0.0400 (11)
H10 −0.810048 −0.971780 0.433307 0.048*
C11 −0.5731 (6) −1.0778 (6) 0.3225 (5) 0.0400 (11)
C12 −0.6592 (6) −1.4017 (6) 0.5025 (6) 0.0429 (12)
H12 −0.757257 −1.390810 0.532367 0.051*
C13 −0.5897 (6) −1.5263 (6) 0.5472 (6) 0.0440 (12)
C14 −0.6355 (7) −1.6003 (6) 0.6648 (6) 0.0484 (13)
C15 −0.5680 (9) −1.7179 (7) 0.7099 (7) 0.0646 (18)
H15 −0.599391 −1.764427 0.791012 0.078*
C16 −0.4567 (9) −1.7628 (7) 0.6339 (9) 0.070 (2)
H16 −0.409836 −1.839501 0.664276 0.084*
C17 −0.4106 (8) −1.6955 (7) 0.5099 (9) 0.0656 (18)
H17 −0.336689 −1.729448 0.456480 0.079*
C18 −0.4764 (7) −1.5787 (7) 0.4687 (7) 0.0541 (14)
H18 −0.445407 −1.533158 0.386994 0.065*
C19 −0.2020 (6) −1.2446 (6) 0.6102 (5) 0.0385 (11)
C20 −0.3133 (6) −1.1548 (6) 0.6348 (6) 0.0425 (12)
H20 −0.331801 −1.087876 0.569180 0.051*
C21 −0.3947 (7) −1.1643 (7) 0.7538 (6) 0.0497 (13)
H21 −0.467896 −1.103943 0.767701 0.060*
C22 −0.3695 (6) −1.2636 (6) 0.8552 (5) 0.0413 (12)
C23 −0.4453 (7) −1.2737 (8) 0.9821 (6) 0.0547 (15)
H23 −0.515830 −1.211885 1.000800 0.066*
C24 −0.4176 (8) −1.3719 (8) 1.0779 (7) 0.0611 (16)
H24 −0.469143 −1.376376 1.160709 0.073*
C25 −0.3116 (8) −1.4661 (8) 1.0519 (7) 0.0610 (16)
H25 −0.294568 −1.534530 1.116569 0.073*
C26 −0.2334 (8) −1.4573 (7) 0.9314 (7) 0.0569 (15)
H26 −0.161094 −1.518319 0.916208 0.068*
C27 −0.2597 (6) −1.3585 (6) 0.8305 (5) 0.0413 (12)
C28 −0.1765 (6) −1.3431 (6) 0.7077 (6) 0.0443 (12)
H28 −0.101912 −1.401611 0.692272 0.053*
C29 −0.0993 (6) −1.2299 (6) 0.4889 (5) 0.0385 (11)
C30 −0.1080 (6) −1.0898 (6) 0.1637 (6) 0.0438 (12)
H30 −0.197078 −1.048472 0.172455 0.053*
C31 −0.0188 (6) −1.0723 (6) 0.0367 (5) 0.0432 (12)
C32 −0.0419 (7) −0.9716 (6) −0.0601 (6) 0.0492 (13)
C33 0.0404 (9) −0.9580 (8) −0.1836 (7) 0.0640 (18)
H33 0.023829 −0.889162 −0.247933 0.077*
C34 0.1452 (9) −1.0492 (9) −0.2057 (7) 0.071 (2)
H34 0.200485 −1.041208 −0.286692 0.085*
C35 0.1717 (7) −1.1517 (8) −0.1130 (7) 0.0600 (16)
H35 0.242625 −1.213069 −0.132250 0.072*
C36 0.0936 (7) −1.1642 (8) 0.0083 (6) 0.0587 (16)
H36 0.113572 −1.232229 0.072192 0.070*
N1 −0.6579 (5) −1.1953 (5) 0.3830 (5) 0.0428 (10)
H1 −0.755881 −1.199970 0.396825 0.051*
N2 −0.5836 (5) −1.3079 (5) 0.4220 (5) 0.0420 (11)
N3 −0.1548 (5) −1.1771 (5) 0.3743 (5) 0.0442 (10)
H3 −0.245893 −1.153536 0.371955 0.053*
N4 −0.0626 (5) −1.1616 (6) 0.2605 (5) 0.0417 (10)
O1 −0.4329 (5) −1.0680 (5) 0.3012 (5) 0.0556 (11)
O2 0.0330 (5) −1.2610 (5) 0.4952 (4) 0.0511 (11)

1 Source of material

2-Naphthohydrazide (1.86 g, 10 mmol) and 2-bromobenzaldehyde (1.85 g, 10 mmol) were dissolved in ethanol (25 mL) and the mixture was refluxed for 6 h. The target compound (3.2 g, yield 91 %) was collected by filtration and washed with ethanol. The crystals of the product can be obtained by recrystallization in ethanol.

2 Experimental details

All hydrogen atoms were identified in difference Fourier syntheses. The U iso values of all hydrogen atoms were set to 1.2 U eq(C).

3 Comment

Hydrazones are important Schiff base ligands with a wide range of biological and pharmaceutical activities. Hydrazone compounds have been screened for antibacterial, anti-tuberculosis, anti-cancer and antioxidant behavior [45]. The structure of hydrazone compounds has received the attention of scientists [6], [7], [8].

In the crystal, the two crystallographically independent molecules adopt an (E) configuration across the C=N bond, joining the hydrazide group and the benzene ring (see the figure). The dihedral angle between rings C1–C10 and C13–C18 is 5.015(17)° and between rings C19–C28 and C31–C36 is 1.858(12)°. The two crystallographically independent adjacent molecules are connected by hydrogen bonds, and the hydrogen bond length of O(1)…N(3)–H(1) is 2.05 Å and the hydrogen bond to the next dimer is 2.08 Å to form a chain structure. The bond lengths of C(1)–C(11), C(11)–O(1), C(11)–N(1), N(1)–N(2), N(2)–C(12), C(12)–C(13) and C(14)–Br(1) are 1.485(7), 1.228(7), 1.346(7), 1.377(6), 1.280(7), 1.463(7) and 1.897(6) respectively. The bond angles of C(11)–N(1)–N(2) and C(12)–N(2)–N(1) are 118.3(4)° and 115.8(4)°. The bond angles of C(1)–C(11)–N(1), C(1)–C(11)–O(1) and O(1)–C(11)–N(1) are 122.4(5)°, 120.6(5)° and 122.4(5)°. The geometric parameters in the second molecule are very similar and fit with the literature [911].


Corresponding author: Zhong-Yan Li, College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou, Hunan, 425199, P. R. China, E-mail:

Funding source: Natural Science Foundation of Hunan Province of China

Award Identifier / Grant number: 2021JJ30291

Funding source: The Scientific Research Fund of Hunan Provincial Education Department

Award Identifier / Grant number: 21A0518, 21C0691

Funding source: Yongzhou Guiding Science and Technology Plan Project (2020, 2021)

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

  2. Research funding: Natural Science Foundation of Hunan Province of China (2021JJ30291), the Scientific Research Fund of Hunan Provincial Education Department (21A0518, 21C0691), Yongzhou Guiding Science and Technology Plan Project (2020, 2021).

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

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Received: 2023-04-28
Accepted: 2023-05-18
Published Online: 2023-06-01
Published in Print: 2023-08-28

© 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. Crystal structure of a polymorph of potassium picrate, C6H2KN3O7
  4. The crystal structure of (1E,2E)-1,2-bis(quinolin-2-ylmethylene)hydrazine, C20H14N4
  5. 5-Amino-2-chloro-4-fluoro-N-(N-isopropyl-N-methylsulfamoyl) benzamide, C11H15O3ClFN3S
  6. Crystal structure of trans-N 1,N 8-bis(2-cyanoethyl)-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, C22H42N6
  7. The crystal structure of [N-{[2-(oxy)-4-methoxyphenyl](phenyl)methylidene}alaninato]-diphenyl-silicon(IV) – chloroform (1/1), C29H25NO4Si·CHCl3
  8. Crystal structure of tetracarbonyl-{μ-[N-(diphenylphosphanyl)-N,P,P-triphenylphosphinous amide]}-bis[μ-(phenylmethanethiolato)]diiron (Fe–Fe), C48H39Fe2NO4P2S2
  9. Crystal structure of baryte from Mine du Pradet (France)
  10. The crystal structure of [(2,2′-bipyridine-6-carboxylato-κ3 N,N,O)-(6-phenylpyridine-2-carboxylate-κ2 N,O)copper(II)] monohydrate, C23H17N3O5Cu
  11. Crystal structure of bis(μ-benzeneselenolato)-(μ-[N-benzyl-N-(diphenylphosphanyl)-P,P-diphenylphosphinous amide])-tetracarbonyl diiron (Fe–Fe), C47H37Fe2NO4P2Se2
  12. The crystal structure of diaqua-methanol-κ1 O- (3-thiophenecarboxylato-κO)-(2,2′-dipyridyl-κ2 N,N′)manganese(II) 3-thiophenecarboxylate, C21H22N2O7S2Mn
  13. Crystal structure of catena-poly[tetrakis(butyl)-μ2-2-((oxido(phenyl)methylene)hydrazineylidene)propanoato-κ4 O:O,O′,N-μ2-2-((oxido(phenyl)methylene)hydrazineylidene)propanoato-κ4 O,N,O′:N′-ditin(IV)], C34H50N6O6Sn2
  14. Crystal structure of 4-chloro-N′-[(1E)-(2-nitrophenyl)methylidene]benzohydrazide, C14H10ClN3O3
  15. The crystal structure of 3-(1′-deoxy-3′,5′-O-dibenzy-β-d-ribosyl)adenine dichloromethane solvate, C49H52Cl2N10O6
  16. The crystal structure of (Z)-4-amino-N′-(1-(o-tolyl)ethylidene)benzohydrazide, C16H17N3O
  17. The co-crystal structure of etoricoxib–phthalic acid (1/1), C18H15ClN2O2S·C8H6O4
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  19. The crystal structure of catena-poly[bis(1-ethylimidazole-k1 N)-(μ 2-benzene-1-carboxyl-3,5-dicarboxylato-κ 2 O, O′)zinc(II)], C19H20N4O6Zn
  20. Crystal structure of 3-(thiazol-2-ylcarbamoyl)-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid, C11H12N2O4S
  21. Rietveld structure analysis of keatite, a rare, metastable SiO2 polymorph
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  23. Crystal structure of 3,5–di-O-benzoyl-1,2-O-isopropylidene-α–D-ribose, C22H22O7
  24. The crystal structure of fac-tricarbonyl(6-bromo-2,2-bipyridine-κ2 N,N)-(nitrato-κO)rhenium(I), C13H7BrN3O6Re
  25. The crystal structure of (E)-N′-(4-hydroxy-3-methoxybenzylidene)-2-naphthohydrazide monohydrate, C19H18N2O4
  26. The crystal structure of 5,5′-diselanediyl-bis(2-hydroxybenzaldehyde), C14H10O4Se2
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  28. Redetermination of the crystal structure of 5,14-dihydro-6,17-dimethyl-8,15-diphenyldibenzo(b,i)(1,4,8,11)tetra-azacyclotetradecine, C32H28N4
  29. Crystal structure of poly[(μ3-2-(3,5-dicarboxyphenyl) benzimidazole-6-carboxylato-κ4O:O:O′:O″)lead(II)] monohydrate, C16H10N2O7Pb
  30. The crystal structure of fac-tricarbonyl(2-pyridin-2-yl-quinoline-κ2 N,N′)-(pyrazole-κN)rhenium(I)nitrate, C20H14N4O3ReNO3
  31. Crystal structure of dibromo-dicarbonyl-bis(tricyclohexylphosphine)-osmium(II) dichloromethane solvate, C38H66Br2O2OsP2
  32. Crystal structure of poly[bis(μ 2-2,6-bis(1-imidazoly)pyridine-κ 2 N:N′)copper(II)] diperchlorate dihydrate, C22H22Cl2CuN10O10
  33. The crystal structure of fac-tricarbonyl(N-benzoyl-N,N-cyclohexylmethylcarbamimidothioato-κ2 S,O)-(pyridine-κN)rhenium(I), C23H24N3O4ReS
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  35. Synthesis and crystal structure of 1-((3R,10S,13S, 17S)-3-((2-methoxyphenyl)amino)-10,13-dimethylhexadecahydro-1H-cyclopenta[α]phenanthren-17-yl)ethan-1-one, C28H41NO2
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  37. The crystal structure of (1-(pyridin-2-yl)-N-(pyridin-2-ylmethyl)-N-((1-(4-vinylbenzyl)-1H-benzo[d]imidazol-2-yl)methyl)methanamine-κ 4 N,N′,N″,N‴)tris(nitrato-kO,O′)-erbium(III), C29H27ErN8O9
  38. Crystal structure of tetracene-5,12-dione, C18H10O2
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  42. Crystal structure of (E)-3-(3-methoxybenzylidene)benzofuran-2(3H)-one, C16H12O3
  43. Synthesis and crystal structure (E)-1-(4-bromo-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one, C11H12BrNO2
  44. Synthesis and crystal structure of (S,E)-4-hydroxy-3-(2-((4aR,6aS,7R,10aS,10bR)-3,3,6a,10b-tetramethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethylidene)dihydrofuran-2(3H)-one, C23H34O5
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  46. The crystal structure of 1-ethyl-2-nitro-imidazole oxide, C5H7N3O3
  47. The crystal structure of 2-(2-fluorophenyl)naphtho[2,1-d]thiazole, C17H10FNS
  48. Crystal structure of (E)-2,4-di-tert-butyl-6-(((2-fluorophenyl)imino) methyl)phenol, C21H26FNO
  49. Synthesis and crystal structure of 3-methyl-2-(methylthio)-4H-chromen-4-one, C12H12O2S
  50. Crystal structure of dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene-5,10-dione, C14H4O2S4
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  52. The crystal structure of N-(6-chloro-2-methyl-2H-indazol-5-yl)acetamide, C10H10ClN3O
  53. Crystal structure of triaqua-(5-bromoisophthalato-κ1 O)-(2,2′-bipyridine-κ2 N:N′)nickel(II) hydrate, C18H19BrN2NiO8
  54. The crystal structure of 2-amino-4-carboxypyridin-1-ium perchlorate, C6H7ClN2O6
  55. The crystal structure of catena-poly[5-aminonicotinic acid-k1 N-m2-bromido-copper(I)], Cu(C6N2H6O2)Br
  56. The crystal structure of 2,2-bis(3-methoxyphenyl)-1-tosyl-1,2-dihydro- 4,3λ4  -[1,3,2]diazaborolo[4,5,1-ij]quinoline - dichloromethane (1/1)
  57. The crystal structure of catena-poly[bis(6-phenylpyridine-2-carboxylato-κ2 N,O)-(μ2-4,4′-bipyridne-κ2 N:N)cadmium(II)], C34H24N4O4Cd
  58. The crystal structure of 5,7-dinitropyrazolo[5,1-b]quinazolin-9(4H)-one, C10H5N5O5
  59. Crystal structure of rac-1,8-bis(2-carbamoylethyl)-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, C22H46N6O2
  60. The crystal structure of (E)-N -(2-bromobenzylidene)-2-naphthohydrazide, C36H26Br2N4O2
  61. The crystal structure of 5-nitronaphthoquinone, C10H5NO4
  62. The crystal structure of (S, R p )-4–benzhydrylideneamino-12-(4-tert-butyl oxazolin-2-yl)[2.2]paracyclophane, C36H36N2O
  63. Synthesis and crystal structure of 2-(2-oxo-2-(o-tolyl)ethyl)-4H-chromen-4-one, C18H14O3
  64. Crystal structure of 2-(thiazol-2-yl)hexahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione, C11H10N2O3S
  65. Crystal structure of N-(diaminomethylene)-1-(dimethylamino)-1-iminiomethanaminium dichloride, C4H13Cl2N5
  66. Crystal structure of poly[(μ3-3, 5-dichloro-2-hydroxy-benzoato-κ4 Cl,O:O′:O″) silver(I)], C7H3AgCl2O3
  67. The crystal structure of tetrakis(1-isopropylimidazole-κ1 N)-[μ2- imidazole-4,5-dicarboxylato-κ4 O,N,O′,N′)]- trioxido-divanadium, C29H41N10O7V2
  68. Crystal structure of catena-[(μ3-bromido)-(1H-1,2,4-triazol-1-yl)benzoato-κ1 N)copper(I)], C9H7BrCuN3O2
  69. The crystal structure of (E)-4-fluoro-N′-(1-(2-hydroxyphenyl)propylidene)benzohydrazide, C16H15FN2O2
Heruntergeladen am 7.9.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2023-0208/html
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