Home Physical Sciences The crystal structure of the co-crystal composed of benzhydrazide and 5-aminoisophthalic acid, C8H7NO4⋅C7H8N2O
Article Open Access

The crystal structure of the co-crystal composed of benzhydrazide and 5-aminoisophthalic acid, C8H7NO4⋅C7H8N2O

  • Jeraldine Maire Bourletidis How ORCID logo , Matthew C. Scheepers ORCID logo , Andreas Lemmerer ORCID logo and Mark G. Smith ORCID logo EMAIL logo
Published/Copyright: October 29, 2024

Abstract

C8H7NO4⋅C7H8N2O, monoclinic, P21/n (no. 14), a = 18.3690(6) Å, b = 3.8010(1) Å, c = 21.5232(7) Å, β = 108.867(1), V = 1422.02(8) Å3, Z = 4, R gt (F) = 0.0340, wR ref (F 2) = 0.0959, T = 173 K.

CCDC no.: 2307503

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: Yellow block
Size: 0.38 × 0.24 × 0.13 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.11 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 28.0°, >99 %
N(hkl)measured , N(hkl)unique, R int: 64276, 3409, 0.052
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 3,194
N(param)refined: 234
Programs: Bruker, 1 SHELX, 2 , 3 ORTEP, 4 WinGX, 5  PLATON 6
Table 2:

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

Atom x y z U iso*/U eq
C1 0.67077 (5) 0.4839 (3) 0.52327 (5) 0.0220 (2)
C2 0.64854 (5) 0.3871 (3) 0.58163 (5) 0.0215 (2)
C3 0.69557 (6) 0.4382 (3) 0.64611 (5) 0.0259 (2)
H3C 0.745701 0.533785 0.65502 0.031*
C4 0.66878 (7) 0.3486 (3) 0.69729 (5) 0.0317 (2)
H4A 0.700354 0.387623 0.741369 0.038*
C5 0.59646 (7) 0.2029 (3) 0.68470 (6) 0.0351 (3)
H5 0.578847 0.139029 0.720076 0.042*
C6 0.54983 (7) 0.1501 (3) 0.62075 (7) 0.0354 (3)
H6 0.500146 0.050023 0.612111 0.043*
N1 0.73497 (5) 0.6721 (2) 0.53332 (4) 0.02459 (19)
H1 0.7645 (8) 0.737 (4) 0.5720 (7) 0.03*
N2 0.75807 (5) 0.7979 (3) 0.48085 (4) 0.02526 (19)
O1 0.63121 (5) 0.3933 (2) 0.46747 (4) 0.0358 (2)
C7 0.57550 (6) 0.2429 (3) 0.56932 (6) 0.0292 (2)
H7 0.543162 0.20826 0.525346 0.035*
C8 0.62663 (5) 0.2308 (3) 0.31247 (5) 0.0231 (2)
C9 0.59276 (5) 0.1998 (3) 0.23993 (5) 0.02112 (19)
C10 0.63734 (5) 0.0515 (3) 0.20534 (5) 0.0227 (2)
H10 0.688242 −0.024467 0.22824 0.027*
C11 0.60787 (5) 0.0135 (3) 0.13737 (5) 0.0226 (2)
C12 0.53323 (6) 0.1313 (3) 0.10492 (5) 0.0238 (2)
H12 0.512502 0.109934 0.058529 0.029*
C13 0.48881 (5) 0.2795 (3) 0.13957 (5) 0.0219 (2)
C14 0.51800 (5) 0.3132 (3) 0.20753 (5) 0.0215 (2)
H14 0.487512 0.411739 0.23136 0.026*
C15 0.40987 (6) 0.4131 (3) 0.10450 (5) 0.0244 (2)
N3 0.65209 (5) −0.1260 (3) 0.10164 (5) 0.0287 (2)
O2 0.68833 (4) 0.1043 (2) 0.34397 (4) 0.03175 (19)
O3 0.58273 (4) 0.4088 (2) 0.33915 (4) 0.03042 (19)
H3 0.6050 (9) 0.414 (4) 0.3824 (9) 0.046*
O4 0.39040 (5) 0.3872 (3) 0.03990 (4) 0.0378 (2)
O5 0.36787 (4) 0.5381 (2) 0.13213 (4) 0.03225 (19)
H3A 0.6925 (10) −0.244 (4) 0.1253 (8) 0.044 (4)*
H3B 0.6236 (10) −0.231 (5) 0.0637 (9) 0.049 (4)*
H2A 0.7175 (9) 0.918 (4) 0.4520 (7) 0.035 (4)*
H2B 0.7696 (9) 0.614 (4) 0.4586 (8) 0.045 (4)*
H4 0.3381 (11) 0.491 (5) 0.0177 (9) 0.064 (5)*

1 Source of materials

Benzhydrazide and 5-amino-isophthalic acid were both purchased commercially and not purified any further. An amount of 0.0214 g of benzhydrazide (0.157 mmol) and 0.0132 g 5-aminoisophthalic acid (0.0728 mmol) were added to a vial and dissolved in 3 ml of AP-grade methanol. The mixture was stirred and heated to 100 °C for 1 min, and then placed in the fridge (8 °C) overnight. The solution was then allowed to slowly evaporate at room temperature with cap being left slightly open. Yellow block crystals formed after three days.

2 Experimental details

C-bound hydrogen atoms were located in the difference map then positioned geometrically and were allowed to ride on their respective parent atoms with thermal displacement parameters 1.2 times of the parent C atom. The coordinates and isotropic displacement parameters of the N-bound and O-bound H atoms involved in hydrogen bonding interactions were allowed to refine freely. Diagrams and publication material were generated using ORTEP-3, 4 WinGX 5 and PLATON. 6

3 Comment

Benzhydrazide also known as benzohydrazide and its derivatives have become popular due to their biological properties, such as anti-bacterial, anti-fungal, anti-cancer and anti-tubercular activity. 7 Benzhydrazide in its pure form crystallizes in the P21/n space group. 8

5-aminoisophthalic acid, a dicarboxylic acid with an amino group is used a lot in the metal organic frameworks of co-ordination chemistry, 9 but is also used in co-crystal engineering. 10 The 5-aminoisophthalic acid can react with a number of aldehydes to form Schiff bases, due to the amino group, by removing water molecules. 11 5–Aminoisophthalic acid in its pure form crystallizes in the Pbcn space group. 12

The benzhydrazide⋅5-aminoisophthalic acid asymmetric unit contains one molecule of benzhydrazide and one molecule of 5-aminoisophthalic acid (see the figure). There is a single hydrogen bond between the two molecules making a discrete hydrogen bond via O1⃛H3c–O3.

With regard to packing, each benzhydrazide molecule is hydrogen bonded to four 5-aminoisophthalic acid molecules via O1⃛H3c–O3, O2⃛H2a–N2, N3⃛H2b–N2, N2⃛H4a–O4 and O5⃛H1–N1. Each aminoterephthalic acid is hydrogen bonded to four benzhydrazide molecules and two aminoterephthalic acid molecules.


Corresponding author: Mark G. Smith, Chemistry Department, University of South Africa, Unisa Science Campus, 28 Pioneer Avenue Florida, Roodepoort, Gauteng, South Africa, E-mail:

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

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

  3. Research funding: This work was supported by the National Research Foundation (NRF) “Competitive Support for Unrated Researchers” grant Number CSUR23042597072 (Dr MG Smith) and the University of South Africa (Ms JMM Bourletidis How).

References

1. Bruker Apex3. Saint–Plus and Xprep; Bruker AXS Inc.: Madison, Wisconsin, USA, 2016.Search in Google Scholar

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

3. Shelxt , 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. Ortep-3, Farrugia, L. J. WinGX and Ortep for Windows: an Update. J. Appl. Crystallogr. 2012, 45, 849–854; https://doi.org/10.1107/s0021889812029111.Search in Google Scholar

5. Farrugia, L. J. WinGX Suite for Small-Molecule Single-Crystal Crystallography. J. Appl. Crystallogr. 1999, 32, 837–838; https://doi.org/10.1107/s0021889899006020.Search in Google Scholar

6. Spek, A. L. Structure Validation in Chemical Crystallography. Acta Crystallogr. 2009, D65, 148–155; https://doi.org/10.1107/s090744490804362x.Search in Google Scholar

7. Kumari, D.; Bansal, H.; Kumari, D.; Benzohydrazides, C. As Potential Bio-Active Agents. Pharm. Innov. 2018, 7, 543–550.Search in Google Scholar

8. Kallel, A.; Amor, B. H.; Svoboda, I.; Fuess, H. Crystal Structure of Benzhydrazide, NH2NHCO(C6H5). Z. Kristallogr. Cryst. Mater. 1992, 198, 137–138; https://doi.org/10.1524/zkri.1992.198.1-2.137.Search in Google Scholar

9. Wang, H. N.; Meng, X.; Qin, C.; Wang, X. L.; Yang, G. S.; Su, Z. M. A Series of Pillar-Layer Metal–Organic Frameworks Based on 5-aminoisophthalic Acid and 4,4′-bipyridine. J. Chem. Soc. 2011, 41, 1047–1053; https://doi.org/10.1039/c1dt11304f.Search in Google Scholar PubMed

10. Mcguire, S. C.; Travis, S. C.; Tuohey, D. W.; Deering, T. J.; Martin, B.; Cox, J. M.; Benedict, J. B. Crystal Structure of the Co-crystal of 5-Amino-Isophthalic Acid and 1,2-Bis(pyridin-4-Yl)ethene. Acta Crystallogr. 2016, E72, 639–642; https://doi.org/10.1107/s2056989016005259.Search in Google Scholar

11. Zhang, L. J.; Qi, L.; Chen, X. Y.; Liu, F.; Liu, L. J.; Ding, W. L.; Li, D. L.; Yuan, G. C.; Tong, J. Z.; Chen, F. Y.; Huang, H. J.; Wang, Y. H. Synthesis, Crystal Structure and Photophysical Properties of Two Reduced Schiff Bases Derived from 5–Aminoisophthalic Acid. J. Chem. Crystallogr. 2019, 49, 260–266; https://doi.org/10.1007/s10870-018-0761-z.Search in Google Scholar

12. Fujii, K.; Sakon, A.; Sekine, A.; Uekusa, H. Reversible Color Switching of an Organic Crystal Induced by Organic Solvent Vapors. Cryst. Growth Des. 2011, 11, 4305–4308; https://doi.org/10.1021/cg2010437.Search in Google Scholar

Received: 2024-08-14
Accepted: 2024-10-18
Published Online: 2024-10-29
Published in Print: 2025-02-25

© 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. New Crystal Structures
  3. Crystal structure of the co-crystal 2,4,6-triamino-1,3,5-triazine-1,3-dioxide — acetic acid (1/2) C7H14N6O6
  4. Crystal structure of the dinuclear mercury(II) complex bis(μ2-bromido)-dibromido-bis{1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-ethyl-5-methyl-imidazol)-κ1 N} dimercury(II), C26H30N10Hg2Br4
  5. Crystal structure of poly[hexaqua-pentakis(μ4-2,2′-bipyridine-4,4′-dicarboxylato-κ4 O:O′:O″:O‴)-(μ2-2,2′-bipyridine-4,4′-dicarboxylato-κ2 O:O)tetraytterbium(III)] hydrate, C36H26N6O16Yb2
  6. Hydrothermal synthesis and crystal structure of catena-poly[(1,10-phenanthroline-κ 2 N,N′)-bis(μ 2-nitroisophthalato-κ 3 O,O′:O″)nickel(II)], C20H13NiN3O7
  7. Crystal structure of 72,73,75,76-tetrafluoro-25,44-dimethyl-31,33,36,38-tetraoxo-31,32,33,36,37,38-hexahydro-3(2,7)-benzo[lmn][3,8]phenanthrolina-1,5(4,1)-dipyridin-1-iuma-2,4(1,2),7(1,4)-tribenzenacyclooctaphane-11,51-diium hexafluoridophosphate, [C46H28F4N4O4][PF6]2, a dicationic cyclophane
  8. Crystal structure of (E)-2-(4-(1H-imidazol-1-yl)benzylidene)-7-fluoro-3,4-dihydronaphthalen-1(2H)-one, C20H15FN2O
  9. The salt crystal structure of etoricoxib hydrochloride, C18H16Cl2N2O2S
  10. The structure of t-butyl 7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate, C37H43FN2O5
  11. The crystal structure of (μ4-oxo)-tri(μ4-2,2′-bipyridine-6,6′-bis(olato)-κ5 O,O′:N:N′:O″)tetrazinc(II) – methylformamide (1/1), C33H25N7O8Zn4
  12. The co-crystal structure of 4-chlorobenzophenone–salicylhydrazide(1/1), C20H17ClN2O3
  13. Crystal structure of 9-fluoro-4-(6-methoxypyridin-2-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C18H15FN4O
  14. The crystal structure of the co-crystal composed of benzhydrazide and 5-aminoisophthalic acid, C8H7NO4⋅C7H8N2O
  15. The cocrystal structure of praziquantel-hesperetin (1/1), C35H38N2O8
  16. Crystal structure of new barium manganese fluorides dihydrates, Ba10Mn2F25·2H2O
  17. The crystal structure of bis[μ2-(3-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)propanoate-κ2O:N)-bis(2,2′-bipyridine-κ2 N, N′)dicopper(II)]dinitrate, C42H36Cu2N12O10
  18. Crystal structure of (3,6-di(2-pyridyl)-4-phenylaminopyridazine-κ2N,N′)-bis(2-(p-toluene)pyridinyl-κ2C,N)-iridium(III) hexafluorophosphate –dichloromethane (1/1), C45H37Cl2F6IrN7P
  19. The crystal structure of 2-(2′-carboxybenzyl)benzoic acid, C15H12O5
  20. The crystal structure of dichlorido-[(E)-N′,N″-bis((2E,3E)-3-(hydroxyimino)butan-2-ylidene)-2-((E)-3-(hydroxyimino)butan-2-ylidene)hydrazine-1-carbohydrazonhydrazide-κ 4 N 4]cobalt(II), C13H22N9O3Cl2Co
  21. Crystal structure of (−)-flavesine H, C15H22N2O2
  22. Crystal structure of 3-methoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C22H22O4
  23. Crystal structure of dicarbonyl(2-oxopyridin-1(2H)-olato-κ 2 O,O)iridium(I), C7H4IrNO4
  24. The crystal structure of 4-(3-(triphenylphosphonio)propyl)piperazin-1-ium dibromide trihydrate, C25H37Br2N2O3P
  25. The crystal structure of ethyl 5,6-dihydroxybenzofuran-3-carboxylate, C11H10O5
  26. Crystal structure of 14-(R)-(2′-cyano-phenoxy)-3,19-diacetyl andrographolide, C31H37NO7
  27. The twinned crystal structure of 10-(4-methyl benzoate)-2,8-diethyl-5,5-difluoro-1,3,7,9-tetramethyl-5H-di-pyrrolo[1,2-c:2′,1′-f] [1,3,2]diazaborinin-4-ium-5-uide, C25H29BF2N2O2
  28. The crystal structure of (9H-thioxanthen-9- ylidene)hydrazine monohydrate, C13H11N2SO0.5
  29. The crystal structure of pyridinium diaqua-{1,2-phenylenebis((carboxylatocarbonyl)amido-κ4 N,N′,O,O′)manganese(III), C15H14MnN3O8
  30. Crystal structure of the hydrogen storage active high entropy phase Tb0.82Sm0.18Ni0.83Co0.17Mg
  31. Crystal structure of diaqua-bis[5-methyl-1-(1H-pyrazol-3-yl)-1H-1,2,3-triazole-4-carboxylato-κ 2 N,O)]manganese(II), C14H16MnN10O6
  32. Crystal structures of diiodido-3-((pyridin-2-ylmethylene)amino)-2-(pyridin-3-yl)-2,3-dihydroquinazolin-4(1H)-one-cadmium(II)
  33. Synthesis and crystal structure of methyl 4-(2-ethoxy-2-oxoethoxy)-3,5-dimethoxybenzoate, C14H18O7
  34. Crystal structure of isoxazolo[4,5-b]pyridin-3-amine, C6H5N3O
  35. Crystal structure of 4-chloro-1-isobutyl-1H-imidazo, C14H14ClN3
  36. The crystal structure of 1,1,1,2,2,2-hexakis(2-methyl-2-phenylpropyl)distannane,C60H78Sn2
  37. The crystal structure of (2,7-dimethoxynaphthalene-1,8-diyl)bis((3-nitrophenyl)methanone), C26H18N2O8
  38. Crystal structure of diaqua-tetra((E)-(RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ 1 N)zinc(II) dinitrate dihydrate, C60H76Cl8N14O14Zn
  39. The crystal structure of diphenyl bis(2-((diphenoxyphosphoryl)amino)ethyl)phosphoramidate monohydrate C40H42N3O10P3
  40. Crystal structure of 4,4′-bis(dibromomethyl)-1,1′-biphenyl, C14H10Br4
  41. Crystal structure of CaPtZn
  42. Crystal structure of 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid, C7H3ClF3NO2
  43. The crystal structure of (3′-(2-bromophenyl)-2-phenyl-[2,2′-bioxiran]-3-yl)(phenyl)methanone, C92H68O12Br4
  44. Crystal structure of ethyl 4-(4-benzylpiperazin-1-yl)benzoate, C20H24N2O2
  45. The crystal structure of bis(selenocyanato-κ1 N)-bis(methanol)-bis((1E,2E)-1,2-bis (1-(pyridin-4-yl)ethylidene)-hydrazine)iron(II) methanol solvate, C34H44FeN10O4Se2
  46. Crystal structure of (E)-1-(5-bromo-2-hydroxyphenyl)-3-(5-(4-methoxyphenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-one, C26H21BrN2O4
  47. The crystal structure of methyl 4-(4-(methylsulfonyl)phenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C19H21NO5S
  48. Crystal structure of 1′,3′-dihydro-2,2′-spirobi[indene]-1,3-dione, C17H12O2
  49. Crystal structure of (E)-2,2′,3,3′-tetrahydro-[1,1′-biindenylidene]-4,4′-diol, C18H16O2
  50. Crystal structure of di-glycylglycinium squarate dihydrate, C12H22N4O12, at 105 K
  51. Crystal structure of {[(4-fluorophenyl)methyl]triphenylphosphonium}dibromocopper(I), [C25H21FP]+[CuBr2]
  52. Crystal structure of poly[diaqua-bis(μ2-5-((pyridin-4-yl-methyl)amino)benzene-1,3-dicarboxylato-κ 2 N:O)cadmium(II)], C28H26CdN4O10
Downloaded on 22.12.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2024-0339/html
Scroll to top button