Home The crystal structure of methyl 3,5-diaminobenzoate, C8H10N2O2
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The crystal structure of methyl 3,5-diaminobenzoate, C8H10N2O2

  • John M. Gardiner , James Raftery , Ian G. Beadham , Jannat N. Azarah , Mohammed Y. Abu-Foul , Adel M. Awadallah and Rami Y. Morjan ORCID logo EMAIL logo
Published/Copyright: December 14, 2022
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 238 Issue 1

Abstract

C8H10N2O2, orthorhombic, Pbca (no. 61), a = 11.0571(2) Å, b = 8.1172(2) Å, c = 17.6080(4) Å, V = 1580.37(6) Å3, Z = 8, R gt (F) = 0.0324, wR ref (F 2) = 0.0872, T = 100(2) K.

CCDC no.: 1519133

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: Brown block
Size: 0.22 × 0.12 × 0.04 mm
Wavelength: Cu Kα radiation (1.54178 Å)
μ: 0.85 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 72.2°, >99%
N(hkl)measured, N(hkl)unique, R int: 7172, 1552, 0.030
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 1383
N(param)refined: 126
Programs: SHELX [1], [2], [3], Bruker [4]
Table 2:

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

Atom x y z U iso*/U eq
C1 0.10499 (10) 0.86389 (13) 0.54508 (6) 0.0175 (3)
C2 0.19368 (10) 0.96328 (14) 0.57782 (6) 0.0181 (2)
H2 0.2675 0.9842 0.5519 0.022*
C3 0.17198 (10) 1.03160 (13) 0.64950 (6) 0.0176 (3)
C4 0.06231 (10) 1.00068 (13) 0.68634 (6) 0.0184 (3)
H4 0.0479 1.0478 0.7349 0.022*
C5 −0.02618 (10) 0.90202 (14) 0.65310 (6) 0.0181 (3)
C6 −0.00405 (10) 0.83186 (14) 0.58180 (6) 0.0183 (3)
H6 −0.0629 0.7630 0.5587 0.022*
C7 0.12825 (10) 0.79163 (14) 0.46850 (6) 0.0186 (3)
C8 0.05297 (12) 0.61452 (16) 0.37332 (7) 0.0275 (3)
H8A 0.0734 0.6985 0.3355 0.041*
H8B −0.0229 0.5605 0.3589 0.041*
H8C 0.1179 0.5324 0.3757 0.041*
N1 0.26091 (10) 1.12400 (12) 0.68744 (6) 0.0220 (2)
N2 −0.13493 (9) 0.86971 (13) 0.69082 (6) 0.0213 (2)
O1 0.21725 (7) 0.81797 (11) 0.43036 (5) 0.0247 (2)
O2 0.03905 (8) 0.69125 (11) 0.44674 (5) 0.0268 (2)
H2A −0.1597 (14) 0.952 (2) 0.7245 (9) 0.027 (4)*
H2B −0.1931 (16) 0.838 (2) 0.6602 (10) 0.035 (4)*
H1B 0.2294 (14) 1.194 (2) 0.7217 (9) 0.032 (4)*
H1A 0.3134 (16) 1.179 (2) 0.6564 (10) 0.035 (4)*

Source of materials

To a solution of methyl 3,5-dinitrobenzoate (3.0 g, 13.3 mmol) [5, 6] in a 1:1 mixture of dry THF (100 mL) and dry ethanol (100 mL) was added 10% Pd–C (1.2 g, 11.3 mmol). The flask was degassed and purged with pure hydrogen for 45 min. The reaction was left stirring for 48 h. The reaction was filtered using Celite-545, and the solution was concentrated by evaporating most of the reaction solvent using a rotary evaporator. The residue was poured into n-hexane (150 mL). The product was filtered and the solvent was removed in vacuo to afford the title compound as brown powder (2.0 g, 91%). A sample of the title compound was dissolved in a mixture of DMSO/EtOH 10:1 v/v and left undisturbed. Unexpectedly the starting material was grown by slow evaporation of the solution over a period of seven days.

Experimental details

The structure was solved by Direct Methods. H atoms were included in calculated positions with C–H lengths of 0.95(CH), 0.99(CH2) & 0.98(CH3) Å; U iso(H) values were fixed at 1.2U eq(C) except for CH3 where it was 1.5U eq(C).

Comment

The title compound molecular structure is shown in the figure. It is a highly planar structure, in which the ester and aromatic ring both occupy the same plane, indicating conjugation of both the CH3O lone pair and the aromatic system with the carbonyl. The X-ray structure revealed close contacts between both of the aromatic amino groups and nearby molecules in the crystal. One aromatic amine has intermolecular NH π-aromatic interactions with a neighboring aromatic system. This is evident from the close contacts between the aromatic NH and aromatic carbons ipso (2.628 Å) and ortho (2.692 and 2.776 Å) to the methyl ester. The other aromatic NH is involved in intermolecular hydrogen bonding with the methyl ester carbonyl oxygen at a distance of 2.265 Å. All bond lengths are in the expected ranges [7].

Corresponding author: Rami Y. Morjan, Department of Chemistry, Faculty of Science, The Islamic University of Gaza, Gaza, Gaza Strip, Palestine, E-mail:

Funding source: TWAS

Award Identifier / Grant number: 16-490 RG/CHE/AF/AC_G – FR3240293296

Acknowledgements

We would like to thank the world academy of sciences for the advancement of science in developing countries TWAS for their financial support. Funding for this research was provided by: the world academy of sciences for the advancement of science in developing countries TWAS (grant no. 16-490 RG/CHE/AF/AC_G – FR3240293296 to Adel M. Awadallah, Rami Y. Morjan); the world academy of sciences for the advancement of science in developing countries TWAS (scholarship no. 16-490 RG/CHE/AF/AC_G – FR3240293296 to Jannat N. Azzara).

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

  2. Research funding: The world academy of sciences for the advancement of science in developing countries TWAS (grant no. 16-490 RG/CHE/AF/AC_G – FR3240293296 to Adel M. Awadallah, Rami Y. Morjan); the world academy of sciences for the advancement of science in developing countries TWAS (scholarship no. 16-490 RG/CHE/AF/AC_G – FR3240293296 to Jannat N. Azarah).

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

References

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Received: 2022-10-05
Accepted: 2022-11-28
Published Online: 2022-12-14
Published in Print: 2023-01-27

© 2022 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 undecacalcium decaarsenide, Ca11As10
  4. Crystal structure of catena-poly[diiodido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-4- ylmethylene)amino)-1,2-dihydro-3H -pyrazol-3-one-κ2 N: O)zinc(II)], C17H16I2N4OZn
  5. The crystal structure of 5,10,15,20-tetrakis(4-(tert-butyl)phenyl)porphyrin-21,23-diido-κ4 N 4-naphthalocyanido-κ4 N 4-neodymium(IV) - chloroform (1/6) C114H90N12Cl18Nd
  6. The crystal structure of 1-(4-bromophenyl)-3-(2-chlorobenzyl)urea, C14H12BrClN2O
  7. Crystal structure of bis[benzyl(methyl)carbamodithioato-κ 2 S,S′]-di-n-butyltin(IV), C26H38N2S4Sn
  8. Crystal structure of (E)-3-(2-(4-(diethylamino)-2-hydroxystyryl)-3,3-dimethyl-3H-indol-1-ium-1-yl)propane-1-sulfonate – methanol (1/2), C25H32N2O4S⋅2CH3OH
  9. Synthesis and crystal structure of {(N′,N″-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))-bis(methaneylylidene))bis(2-hydroxybenzohydrazonato)-κ6 N 2 O 4}copper(II), C30H24CuN4O6
  10. The crystal structure of ((E)-2,4-dibromo-6-(((5-(nitro)-2-oxidophenyl)imino)methyl)phenolato-κ 3 N,O,O′)tris(pyridine-κN)manganese(II), C28H21Br2MnN5O4
  11. Synthesis and crystal structure of 1-((3R,10S,13R,17S)-10,13-dimethyl-3-(p-tolylamino)hexadecahydro-1H-cyclopenta-[a]phenanthren-17-yl)ethan-1-one, C28H41NO
  12. The crystal structure of 3-nitrobenzene-1,2-dicarboxylic acid—pyrazine-2-carboxamide(1/1), C13H10N4O7
  13. Crystal structure of poly[tetrakis(μ3-2-aminonicotinato-κ3N,O,O′)-(μ2-oxalato-κ4 O,O′:O″,O′″)-(μ4-oxalato-κ6 N:N′:O,O′:O″,O′″)dicopper(I)-disamarium(III)], [SmCu(C6N2H5O2)2(C2O4)] n
  14. The crystal structure of 2,3,4-trihydroxybenzoic- acid—pyrazine-2-carboxamide—water (1/1/1), C12H13N3O7
  15. Crystal structure of N-ethyl-4-[3-(trifluoromethyl)-phenyl]piperazine-1-carbothioamide, C14H18F3N3S
  16. The crystal structure of 3-anilino-1,4-diphenyl-4H-1,2,4-triazol-1-ium iodide, C20H17N4I
  17. The crystal structure of (tris(2-benzimidazolylmethyl)amine)-benzoato-copper(II) perchlorate monohydrate, CuC31H28N7O7Cl
  18. Crystal structure of [2-hydroxy-3-methyl-benzoato-k1 O-triphenyltin(IV)], C26H22O3Sn
  19. Crystal structure of diaqua-bis(4-(hydroxymethyl)-benzoato-k1 O)zinc(II), C16H18O8Zn
  20. The crystal structure of dicarbonyl-(N-nitroso-N-oxido-phenylamine-κ 2 O,O)-rhodium(I), C8H5N2O4Rh
  21. The crystal structure of oxalic acid – 2-ethoxybenzamide (2/1), C20H24N2O8
  22. The crystal structure of ethyl 7-ethyl-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, C10H15N5O2
  23. Crystal structure of poly[(N,N-dimethylacetamide-κO) (μ4-2-nitroisophthalato-κ 4 O:O′:O″:O′″)manganese(II)], C11H10N2O7Mn
  24. Crystal structure of 14-O-acetyldelcosine, C26H41NO8
  25. The crystal structure of poly[(1,10-phenanthroline-κ2 N,N′)-(μ 4-2-chlorobenzene-1,3-dicarboxylato-κ5 O:O′:O″:O‴) cadmium(II)] monohydrate, C20H13CdClN2O5
  26. Crystal structure of propane-1,3-diylbis(diphenylphosphine sulfide) ethanol solvate, C27H26P2S2
  27. Crystal structure of bis{[(4-diethylamino-2-hydroxy-benzylidene)-hydrazinocarbonylmethyl]-trimethylammonium} tetrabromozincate, C32H54N8O4ZnBr4
  28. Synthesis and crystal structure of dimethyl 2,2′-(2,5-bis(4-hydroxyphenyl)-2,5-dihydrofuran-3,4-diyl)dibenzoate, C34H30O7
  29. Synthesis and crystal structure of 2-(2-oxo-2-phenylethyl)-4H-chromen-4-one, C17H12O3
  30. The crystal structure of tetra(imidazole-κ1 N)zinc(II) μ2-oxido-hexaoxido-divanadium(VI) C12H16N8O6V2Zn
  31. Crystal structure of S-2-(1-(5-methylpyridin-2-ylamino)octyl)-3-hydroxynaphthalene-1,4-dione, C24H28N2O3
  32. Crystal structure of bis(μ2-5-chloro-2-oxido-N-(1-oxido-2-oxo-2-phenylethylidene)-benzohydrazonato-κ5 N,O,O′:N′,O′′)-oktakis(pyridine-κ1 N)trinickel(II) – methanol – pyridine (1/1/1) C76H65N13Cl2Ni3O9
  33. The crystal structure of methyl 3,5-diaminobenzoate, C8H10N2O2
  34. Crystal structure of 10-(9H-carbazol-9-yl)-5H-dibenzo[a,d][7]annelen-5-one, C27H17NO
  35. Crystal structure of ethyl 1-(2-hydroxyethyl)-4-((4-methoxyphenyl)amino)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate, C16H20N2O5
  36. The crystal structure of 1-(4-bromophenyl)-3-cycloheptylurea, C14H19BrN2O
  37. The crystal structure of 1,4-bis(1,2,3,4,5-pentamethylcyclopenta-2,4-dien-1-yl)-3,6-bis ((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene)-1,4-dialuminacyclohexane – benzene (1/2), C50H72Al2B2O4
  38. Crystal structure of bis(μ 3-diphenylphosphinato)-tetrakis(μ 2-diphenylphosphinato)-bis(diphenylphosphinato)-bis(μ 2-hydroxo)dicopper(II)-ditin(IV), C104H100O18P8Cu2Sn2
  39. Crystal structure of 3-((3,4-dichloroisothiazol-5-yl)methoxy)benzo[d] isothiazole 1,1-dioxide, C11H6Cl2N2O3S2
  40. Synthesis and crystal structure of 2-(2-(2-fluorophenyl)-2-oxoethyl)-4H-chromen-4-one, C17H11FO3
  41. The crystal structure of tris(carbonyl)-bis(carbonyl)-[μ-propane-1,2- dithiolato]-(benzyldiphenylphosphine)diiron (Fe—Fe), C27H23Fe2O5PS2
  42. Crystal structure of 1-(2-(4-chlorophenethyl)-2-hydroxy-3,3-dimethylbutyl)-1H-1,2,4-triazol-4-ium nitrate, C16H23N4O4Cl
  43. The crystal structure of 3,3′-disulfanediyldi(1H-1,2,4-triazol-5-amine) monohydrate, C4H8N8OS2
  44. The crystal structure of trans-[bis(4-methylpyridine-κN)bis(quinoline-2-carboxylato- κ 2 N,O)cadmium(II)], C32H26CdN4O4
  45. The crystal structure of ethyl 2′-hydroxy-4′,6′-dimethoxy-3-(4-methoxynaphthalen-1-yl)-5-oxo-2,3,4,5-tetrahydro-[1,1′-biphenyl]-4-carboxylate, C28H28O7
https://doi.org/10.1515/ncrs-2022-0485
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of undecacalcium decaarsenide, Ca11As10
  4. Crystal structure of catena-poly[diiodido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-4- ylmethylene)amino)-1,2-dihydro-3H -pyrazol-3-one-κ2 N: O)zinc(II)], C17H16I2N4OZn
  5. The crystal structure of 5,10,15,20-tetrakis(4-(tert-butyl)phenyl)porphyrin-21,23-diido-κ4 N 4-naphthalocyanido-κ4 N 4-neodymium(IV) - chloroform (1/6) C114H90N12Cl18Nd
  6. The crystal structure of 1-(4-bromophenyl)-3-(2-chlorobenzyl)urea, C14H12BrClN2O
  7. Crystal structure of bis[benzyl(methyl)carbamodithioato-κ 2 S,S′]-di-n-butyltin(IV), C26H38N2S4Sn
  8. Crystal structure of (E)-3-(2-(4-(diethylamino)-2-hydroxystyryl)-3,3-dimethyl-3H-indol-1-ium-1-yl)propane-1-sulfonate – methanol (1/2), C25H32N2O4S⋅2CH3OH
  9. Synthesis and crystal structure of {(N′,N″-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))-bis(methaneylylidene))bis(2-hydroxybenzohydrazonato)-κ6 N 2 O 4}copper(II), C30H24CuN4O6
  10. The crystal structure of ((E)-2,4-dibromo-6-(((5-(nitro)-2-oxidophenyl)imino)methyl)phenolato-κ 3 N,O,O′)tris(pyridine-κN)manganese(II), C28H21Br2MnN5O4
  11. Synthesis and crystal structure of 1-((3R,10S,13R,17S)-10,13-dimethyl-3-(p-tolylamino)hexadecahydro-1H-cyclopenta-[a]phenanthren-17-yl)ethan-1-one, C28H41NO
  12. The crystal structure of 3-nitrobenzene-1,2-dicarboxylic acid—pyrazine-2-carboxamide(1/1), C13H10N4O7
  13. Crystal structure of poly[tetrakis(μ3-2-aminonicotinato-κ3N,O,O′)-(μ2-oxalato-κ4 O,O′:O″,O′″)-(μ4-oxalato-κ6 N:N′:O,O′:O″,O′″)dicopper(I)-disamarium(III)], [SmCu(C6N2H5O2)2(C2O4)] n
  14. The crystal structure of 2,3,4-trihydroxybenzoic- acid—pyrazine-2-carboxamide—water (1/1/1), C12H13N3O7
  15. Crystal structure of N-ethyl-4-[3-(trifluoromethyl)-phenyl]piperazine-1-carbothioamide, C14H18F3N3S
  16. The crystal structure of 3-anilino-1,4-diphenyl-4H-1,2,4-triazol-1-ium iodide, C20H17N4I
  17. The crystal structure of (tris(2-benzimidazolylmethyl)amine)-benzoato-copper(II) perchlorate monohydrate, CuC31H28N7O7Cl
  18. Crystal structure of [2-hydroxy-3-methyl-benzoato-k1 O-triphenyltin(IV)], C26H22O3Sn
  19. Crystal structure of diaqua-bis(4-(hydroxymethyl)-benzoato-k1 O)zinc(II), C16H18O8Zn
  20. The crystal structure of dicarbonyl-(N-nitroso-N-oxido-phenylamine-κ 2 O,O)-rhodium(I), C8H5N2O4Rh
  21. The crystal structure of oxalic acid – 2-ethoxybenzamide (2/1), C20H24N2O8
  22. The crystal structure of ethyl 7-ethyl-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, C10H15N5O2
  23. Crystal structure of poly[(N,N-dimethylacetamide-κO) (μ4-2-nitroisophthalato-κ 4 O:O′:O″:O′″)manganese(II)], C11H10N2O7Mn
  24. Crystal structure of 14-O-acetyldelcosine, C26H41NO8
  25. The crystal structure of poly[(1,10-phenanthroline-κ2 N,N′)-(μ 4-2-chlorobenzene-1,3-dicarboxylato-κ5 O:O′:O″:O‴) cadmium(II)] monohydrate, C20H13CdClN2O5
  26. Crystal structure of propane-1,3-diylbis(diphenylphosphine sulfide) ethanol solvate, C27H26P2S2
  27. Crystal structure of bis{[(4-diethylamino-2-hydroxy-benzylidene)-hydrazinocarbonylmethyl]-trimethylammonium} tetrabromozincate, C32H54N8O4ZnBr4
  28. Synthesis and crystal structure of dimethyl 2,2′-(2,5-bis(4-hydroxyphenyl)-2,5-dihydrofuran-3,4-diyl)dibenzoate, C34H30O7
  29. Synthesis and crystal structure of 2-(2-oxo-2-phenylethyl)-4H-chromen-4-one, C17H12O3
  30. The crystal structure of tetra(imidazole-κ1 N)zinc(II) μ2-oxido-hexaoxido-divanadium(VI) C12H16N8O6V2Zn
  31. Crystal structure of S-2-(1-(5-methylpyridin-2-ylamino)octyl)-3-hydroxynaphthalene-1,4-dione, C24H28N2O3
  32. Crystal structure of bis(μ2-5-chloro-2-oxido-N-(1-oxido-2-oxo-2-phenylethylidene)-benzohydrazonato-κ5 N,O,O′:N′,O′′)-oktakis(pyridine-κ1 N)trinickel(II) – methanol – pyridine (1/1/1) C76H65N13Cl2Ni3O9
  33. The crystal structure of methyl 3,5-diaminobenzoate, C8H10N2O2
  34. Crystal structure of 10-(9H-carbazol-9-yl)-5H-dibenzo[a,d][7]annelen-5-one, C27H17NO
  35. Crystal structure of ethyl 1-(2-hydroxyethyl)-4-((4-methoxyphenyl)amino)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate, C16H20N2O5
  36. The crystal structure of 1-(4-bromophenyl)-3-cycloheptylurea, C14H19BrN2O
  37. The crystal structure of 1,4-bis(1,2,3,4,5-pentamethylcyclopenta-2,4-dien-1-yl)-3,6-bis ((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene)-1,4-dialuminacyclohexane – benzene (1/2), C50H72Al2B2O4
  38. Crystal structure of bis(μ 3-diphenylphosphinato)-tetrakis(μ 2-diphenylphosphinato)-bis(diphenylphosphinato)-bis(μ 2-hydroxo)dicopper(II)-ditin(IV), C104H100O18P8Cu2Sn2
  39. Crystal structure of 3-((3,4-dichloroisothiazol-5-yl)methoxy)benzo[d] isothiazole 1,1-dioxide, C11H6Cl2N2O3S2
  40. Synthesis and crystal structure of 2-(2-(2-fluorophenyl)-2-oxoethyl)-4H-chromen-4-one, C17H11FO3
  41. The crystal structure of tris(carbonyl)-bis(carbonyl)-[μ-propane-1,2- dithiolato]-(benzyldiphenylphosphine)diiron (Fe—Fe), C27H23Fe2O5PS2
  42. Crystal structure of 1-(2-(4-chlorophenethyl)-2-hydroxy-3,3-dimethylbutyl)-1H-1,2,4-triazol-4-ium nitrate, C16H23N4O4Cl
  43. The crystal structure of 3,3′-disulfanediyldi(1H-1,2,4-triazol-5-amine) monohydrate, C4H8N8OS2
  44. The crystal structure of trans-[bis(4-methylpyridine-κN)bis(quinoline-2-carboxylato- κ 2 N,O)cadmium(II)], C32H26CdN4O4
  45. The crystal structure of ethyl 2′-hydroxy-4′,6′-dimethoxy-3-(4-methoxynaphthalen-1-yl)-5-oxo-2,3,4,5-tetrahydro-[1,1′-biphenyl]-4-carboxylate, C28H28O7
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