Startseite The crystal structure of the co-crystal isonicotinamide · terephthalic acid, C8H6O4·2(C6H6N2O)
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The crystal structure of the co-crystal isonicotinamide · terephthalic acid, C8H6O4·2(C6H6N2O)

  • Jeraldine Maire Bourletidis How ORCID logo , Matthew C. Scheepers , Andreas Lemmerer und Mark G. Smith ORCID logo EMAIL logo
Veröffentlicht/Copyright: 1. Oktober 2024

Abstract

C8H6O4·2(C6H6N2O), monoclinic, C2/c (no. 15), a = 20.8371(8) Å, b = 5.2243(2) Å, c = 19.1062(7) Å, β = 118.8350(10)°, V = 1822.01(12) Å3, Z = 4, R gt(F) = 0.0392, wR ref(F 2) = 0.1143, T = 173 K.

CCDC No.: 2312436

A part of 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: Colourless block
Size: 0.23 × 0.23 × 0.16 mm
Wavelength:

μ:
MoKα radiation (0.71073 Å)

0.11 mm−1
Diffractometer, scan mode:

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

28.0°, >99 %
N(hkl)measuredN(hkl)uniqueR int: 70443, 2192, 0.072
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 2039
N(param)refined: 145
Programs: Bruker, 1 SHELX, 2 , 3 WinGX/ORTEP, 4 , 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 0.71011 (6) 0.0511 (2) 0.92254 (6) 0.0177 (2)
C2 0.68410 (6) 0.2670 (2) 0.86261 (6) 0.0174 (2)
C3 0.61103 (6) 0.3308 (2) 0.81364 (6) 0.0226 (2)
H3 0.573074 0.239098 0.816682 0.027*
C4 0.59482 (6) 0.5317 (2) 0.76020 (7) 0.0247 (3)
H4 0.544891 0.576115 0.72693 0.03*
C5 0.71612 (6) 0.6034 (2) 0.80038 (7) 0.0240 (3)
H5 0.752816 0.698156 0.795769 0.029*
C6 0.73743 (6) 0.4066 (2) 0.85563 (6) 0.0213 (2)
H6 0.787858 0.367601 0.888323 0.026*
C7 0.54169 (6) 1.0976 (2) 0.61722 (6) 0.0190 (2)
C8 0.52041 (5) 1.3060 (2) 0.55635 (6) 0.0190 (2)
C9 0.44791 (6) 1.3868 (2) 0.51581 (7) 0.0233 (2)
H9 0.412388 1.309382 0.526659 0.028*
C10 0.42753 (6) 1.5807 (2) 0.45947 (7) 0.0229 (2)
H10 0.377997 1.636165 0.431691 0.027*
N1 0.66025 (5) −0.08271 (18) 0.93140 (6) 0.0208 (2)
N2 0.64600 (5) 0.66505 (18) 0.75337 (5) 0.0226 (2)
O1 0.77626 (4) 0.00541 (16) 0.95997 (5) 0.0241 (2)
O2 0.61088 (4) 1.03262 (17) 0.64992 (5) 0.0257 (2)
O3 0.49838 (4) 0.99942 (16) 0.63526 (5) 0.0249 (2)
H1A 0.6766 (8) −0.215 (3) 0.9659 (9) 0.03*
H1B 0.6108 (9) −0.049 (3) 0.9062 (9) 0.03*
H2 0.6223 (9) 0.898 (3) 0.6887 (10) 0.037*

1 Source of materials

Isonicotinamide and terephthalic acid were commercially sourced and not purified any further. 0.0204 g of isonicotinamide (0.167 mmol) and 0.0162 g terephthalic acid (0.0975 mmol) were dissolved in 1 ml of AP grade methanol while stirring at 50 °C. 200 μl of AP grade dimethyl sulphoxide was then added to the solution, which was then heated to 100 °C while stirring in a polytop vial. The solution was left to evaporate at room temperature, with the cap being left slightly open. Colourless block crystals formed after 10 days.

2 Experimental details

First the non-hydrogen atoms were refined isotropically, then anisotropically by full matrix least-squares calculations based on F 2. C-bound hydrogen atoms were placed at idealized positions 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 isotropically. Diagrams and publication material were generated using ORTEP-3, 4 WinGX 5 and PLATON. 6

3 Comment

Isonicotinamide is an isomer of niacinamide, differing in the position of the carbamide substituent. Isonicotinamide, like niacinamide, is thought to be very useful in co-crystallization because the pyridine nitrogen easily acts as an acceptor for hydrogen bonds, especially when paired with good hydrogen bond donors, such as carboxylic acids and alcohols. Isonicotinamide has been co-crystallized with many carboxylic acids, making use of the robust carboxylic acid⃛pyridine hydrogen bond. 7 Isonicotinamide in its pure form crystallizes in the P21/c space group. 8

Terephthalic acid, a dicarboxylic acid is used in the synthesis of metal organic frameworks as a linker between metal centres. It is also commonly used to prepare co-crystals with N-heterocyclic molecules. 9 It is also frequently used in the development of saturated polyesters. 10 Terephthalic acid is also useful when preparing co-ordination polymers. 11 Terephthalic acid in its pure form crystallizes in the P1̄ space group. 12

The asymmetric unit of isonicotinamide ⋅ terephthalic contains one molecule of isonicotinamide and half a molecule of terephthalic acid, and crystallizes in the monoclinic C2/c space group. The complete molecule is generated by symmetry. There is an O2–H2⃛N2 hydrogen bond, formed between the hydrogen of the carboxyl group and the pyridine nitrogen atom. Being in the C2/c space group the crystal structure has a glide plane along the c axis. The isonicotinamide molecule is bonded to another isonicotinamide molecule through N1–H1A⃛O1 hydrogen bonds, forming an R(8) ring, and two terephthalic acid molecules via O2–H2⃛N2 and N1–H1B⃛O3 hydrogen bonds. Terephthalic acid is bonded to four isonicotinamide molecules via two N1–H1B⃛O3 hydrogen bonds and two O2–H2⃛N2 hydrogen bonds.


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. Competing interests: 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) as well as the University of South Africa.

References

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Received: 2024-07-23
Accepted: 2024-09-16
Published Online: 2024-10-01
Published in Print: 2024-12-17

© 2024 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 3-nitrophenol-2,1,3-benzoselenadiazole (1/1), C12H9N3O3Se
  4. Crystal structure of diaqua-(hydroxido)-{μ-[2-(hydroxy)-5-[(4-nitrophenyl)diazenyl]benzoato]}-{2-hydroxy-5-[(4-nitrophenyl)diazenyl]benzoato}-(1,10-phenanthroline)-diterbium hydrate, C38H27.4N8O12.2Tb
  5. Crystal structure of poly[bis(μ3-3-fluoro-4-(1H-1,2,4-triazol-1-yl)benzoato-κ3 O:O′:N)cadmium(II)] – dimethylformamide (1/1), C21H17CdF2N7O5
  6. The crystal structure of 2-amino-N-(pyridin-2-yl)benzamide, C12H11N3O
  7. The crystal structure of 2,3-di(pyridin-2-yl)-2,3-dihydroquinazolin-4(1H)-one, C18H14N4O
  8. Crystal structure of 2-chloro-4-fluorobenzyl (R)-2-(6-methoxynaphthalen-2-yl)propanoate, C21H18ClFO3
  9. Crystal structure of [1-(4-carboxyphenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylic acid]-(methylsulfinyl)methane, C15H16N2O6S
  10. The crystal structure of 2-ethyl-1,1-dimethyl-1H-benzo[e]indole, C16H17N
  11. The crystal structure of (Z)-5-amino-N -hydroxy-1H-pyrazole-4-carboximidamide, C4H7N5O
  12. The crystal structure of 2,2,5-trimethyl-3-(4-(4-(5-phenyl-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)phenyl)imidazolidin-4-one, C24H24N4O2S
  13. The crystal structure of tetrakis(μ2-acetato-κ2 O:O′)-bis[(4′-phenyl-4,2′:6′,4″-terpyridine-κ1 N)dicopper(II)], C25H21CuN3O4
  14. Crystal structure of poly(3-thiophenecarboxylato-κ 3 O,O′:O′)-(methanol-κO)cadmium(II), C11H10O5S2Cd
  15. The crystal structure of dichloridobis[4′-(p-methoxylphenyl)-4,2′:6′,4″-terpyridine-κN] zinc(II), C44H34Cl2N6O2Zn
  16. The crystal structure of 1-(2-carboxyethyl)-1H-imidazole 3-oxide
  17. Crystal structure of 1,1′,1″-(nitrilotris(ethane-2,1-diyl))tris(3-(4-(((E)-pyridin-2-ylmethylene)amino)phenyl)urea), C45H47N13O4
  18. Crystal structure of a (E)-4-bromo-N-(4-(diethylamino)-2-hydroxybenzylidene) benzenaminium acetate ─ 4-bromoaniline (1/1)
  19. Crystal structure of 2,2′-(iminobis(methylene))bis(benzimidazolium) bis(p-toluenesulfonate), C30H31N5O6S2
  20. The crystal structure of alogliptinium meta-chlorobenzoate
  21. Crystal structure of 4-bromobenzyl 2-(6-methoxy-naphthalen-2-yl)propanoate, C21H19BrO3
  22. The hydrated double salt structure of (E)-4-(2-benzylidenehydrazine-1-carbonyl)pyridin-1-ium cation with 2-hydroxybenzoate and benzoate anions
  23. Crystal structure of (R)(R)-5-chloro-3-((S,1E,3E)-3,5-dimethyl-hepta-1,3-dien-1-yl)-7-methyl-6,8-dioxo-2,6,7,8-tetrahydroisoquinolin-7-yl acetate, C21H24ClNO4
  24. The crystal structure of bis(3-oxo-1,3-diphenylprop-1-en-1-olato-κ 2 O:O′)-bis(1,4-dioxane-κ 1 O)nickel(II), C38H38O8Ni
  25. Crystal structure of poly[aqua-(pyridine-3-carboxylato-κ1 N)(pyridine-3-carboxylato-κ2 O,O′) cadmium(II)] dihydrate, C12H14N2O7Cd
  26. The crystal structure of 4-(4-phenyl-5-(((1-(2,4,6-tribromophenyl)-1H-1,2,3-triazol-4-yl)methyl)thio)-4H-1,2,4-triazol-3-yl)pyridine, C22H14Br3N7S
  27. The crystal structure of N-benzylquinoline-2-carbothioamide, C17H14N2S
  28. Crystal structure of bis(3-isopropylphenyl)-4,4′-bipyridinium dichloride dihydrate, C28H30N2⋅2Cl⋅2H2O
  29. The crystal structure of ethyl 2-amino-4-(cyanophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C19H18N2O4
  30. Crystal structure of (4R,10S)-6-hydroxy-7-isopropyl-4,10-dimethyl-1,2,3,5-hexahydro-6,10-epoxyazulen-9-one, C15H22O3
  31. The crystal structure of (E)-(2-(2-hydroxy-3-methoxybenzylidene)aminophenyl)arsonic acid, C14H14AsNO5
  32. The crystal structure of poly[(μ 2-2-aminoisophthalato-κ4O,O′:O″:O″′)-(N-methylpyrrolidone κ1O)-dioxido-uranium(VI)], C13H14N2O7U
  33. The crystal structure of the co-crystal isonicotinamide · terephthalic acid, C8H6O4·2(C6H6N2O)
  34. The crystal structure of (E)-1-phenyl-3-(p-tolylthio)but-2-en-1-one, C17H16OS
  35. The crystal structure of 4,5-bis((Z)-chloro(hydroxyimino)methyl)-1H-imidazol-3-ium chloride monohydrate
  36. The crystal structure of 1,2-bis(4-(dimethylamino)phenyl)ethane-1,2-dione. C18H20N2O2
  37. Crystal structure of 2-chloro-4-fluorobenzyl 2-acetoxybenzoate, C16H12ClFO4
  38. Crystal structure of methyl 1-phenyl-9H-pyrido[3,4-b]indole-3-carboxylate, C19H14N2O2
  39. Crystal structure of (3-(dimethoxymethyl)-5-methoxy-1H-indol-1-yl)(5-fluoro-2-iodophenyl)methanone, C19H17FINO4
  40. Crystal structure of tetrachlorido-bis(1-[(1H-triazole-1-yl)methyl]-1H-benzotriazole-κ2 N:N′)dicopper, C36H32Cu2N24Cl4
  41. Crystal structure of 2-(2,3-bis(4-methoxyphenyl)-1H-pyrrolo[2,3-b]quinoxalin-1-yl)anilin, C30H24N4O2
  42. Crystal structure of 5,7-dihydroxy-2-phenyl-4H-chromen-4-one–N,N-dimethylformamide(1/1), C18H17NO5
  43. The crystal structure of bis(μ 2-biphenyl-2,2′-dicarboxylato)-diaqua-bis(nitrato)-bis(2,2′:6′,2′′-terpyridine)dineodymium(III), C46H32I2N8Nd2O16
  44. Crystal structure of (Z)-4-amino-N -((4-chlorophenyl)(phenyl)methylene)benzohydrazide, C20H16ClN3O
  45. Crystal structure of (E)-6,8-dimethoxy-4-(4-morpholinobenzylidene)-3,4-dihydro-1-benzoxepin-5(2H)-one, C23H25NO5
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  47. The crystal structure of [triaqua-(8-carboxymethoxy-quinoline-2-carboxylato-κ 3 N,O,O)copper(II)]monohydrate, C12H15NO9Cu
  48. Crystal structure of (((4-chlorophenyl)sulfonyl)glycinato-κ 2 N,O)bis(1,10-phenanthroline-κ 2 N,N′)cobalt(II) tetrahydrate, C32H30ClCoN5O8S
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  50. Crystal structure of 3-phenoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C27H24O4
  51. 6-(2′,3′-Dihydroxy-3′-methylbutyl)-7-methoxy-8-(3″-methylbut-2″-en-1″-yl)-2H-chromen-2-one, C20H26O5
  52. Crystal structure of bromido-(2,2′:6′,2″-terpyridine-4′-onato-κ3N)palladium(II) methanol solvate
  53. The crystal structure of ethyl 2-amino-(4-nitrophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C20H22N2O6
  54. Crystal structure of (1E,3E,5E)-1,6-bis(4-(pentyloxy)phenyl)hexa-1,3,5-triene, C28H36O2
  55. The crystal structure of tris(2-bromo-4-methylphenyl)amine, C21H18Br3N
  56. The crystal structure of 3-(2,5-dimethylanilino)-1-(2,5-dimethylphenyl)-4-methyl-1H-pyrrole-2,5-dione, C21H22N2O2
  57. Crystal structure of dicarbonyl (μ2-indole-2-carboxylato κ2 O:O′)tris(triphenylarsine-κAs)dirhodium(I) acetone solvate, C68H56As3NO5Rh2
  58. The crystal structure of 4-chloro-2-formylphenyl 4-methylbenzenesulfonate, C14H11ClO4S
  59. Crystal structure of 4-iodobenzyl 2-(6-methoxynaphthalen-2-yl) propanoate, C21H19IO3
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