Home Synthesis and crystal structure of 1-(7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)-N,N-dimethylmethanaminiumnitrate, C18H17N3O9
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Synthesis and crystal structure of 1-(7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)-N,N-dimethylmethanaminiumnitrate, C18H17N3O9

  • Hai-Lin Chen ORCID logo , Dong-Mei Yao , Ze-Ping Luo , Yan-Ping Wang and Yu-Mei Tang
Published/Copyright: August 1, 2023
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 238 Issue 5

Abstract

C18H17N3O9, monoclinic, P21/c (no. 14), a = 15.3768(3) Å, b = 7.4510(2) Å, c = 15.6673(5) Å, β = 102.700(3)∘, V = 1751.13(8) Å3, Z = 4, R gt (F) = 0.0405, wR ref (F 2 ) = 0.1157, T = 100 K.

CCDC no.: 2282765

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: Yellow needle
Size: 0.20 × 0.15 × 0.13 mm
Wavelength: Cu Kα radiation (1.54178 Å)
μ: 1.12 mm−1
Diffractometer, scan mode: φ and ω
θmax, completeness: 75.5°, 96 %
N(hkl)measured, N(hkl)unique, Rint: 8608, 3365, 0.031
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 2867
N(param)refined: 275
Programs: Rigaku [1], Diamond [2], SHELX [3, 4]
Table 2:

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

Atom x y Z Uiso*/Ueq
O1 0.12061 (7) 0.69595 (17) 0.37594 (7) 0.0244 (3)
H1 0.113052 0.634840 0.418784 0.037*
O2 0.53339 (7) 0.58249 (16) 0.39153 (7) 0.0235 (3)
O3 0.32749 (6) 0.75673 (15) 0.19759 (7) 0.0198 (2)
O4 0.82537 (7) 0.70179 (17) 0.16493 (8) 0.0256 (3)
H4 0.823354 0.693987 0.111048 0.038*
O5 0.73960 (7) 0.64011 (19) 0.00372 (8) 0.0322 (3)
O6 0.60442 (8) 0.54183 (19) −0.02255 (8) 0.0316 (3)
N1 0.09657 (8) 0.68739 (18) 0.15205 (8) 0.0192 (3)
H1A 0.052415 0.763503 0.111274 0.023*
N2 0.66921 (8) 0.6071 (2) 0.02719 (9) 0.0238 (3)
C1 0.20526 (9) 0.6755 (2) 0.36637 (10) 0.0200 (3)
C2 0.27290 (10) 0.6086 (2) 0.43455 (10) 0.0216 (3)
H2 0.259206 0.572554 0.488261 0.026*
C3 0.35888 (9) 0.5956 (2) 0.42317 (10) 0.0202 (3)
H3 0.404482 0.551862 0.469589 0.024*
C4 0.38002 (9) 0.6459 (2) 0.34403 (10) 0.0186 (3)
C5 0.31153 (9) 0.7085 (2) 0.27698 (10) 0.0175 (3)
C6 0.22313 (9) 0.7269 (2) 0.28627 (10) 0.0181 (3)
C7 0.47196 (9) 0.6341 (2) 0.33206 (10) 0.0190 (3)
C8 0.48336 (9) 0.6853 (2) 0.24492 (10) 0.0187 (3)
C9 0.41175 (9) 0.7431 (2) 0.18478 (10) 0.0198 (3)
H9 0.421175 0.776801 0.129042 0.024*
C10 0.57229 (9) 0.6802 (2) 0.22197 (10) 0.0191 (3)
C11 0.58094 (9) 0.6404 (2) 0.13793 (10) 0.0204 (3)
H11 0.529840 0.607637 0.094657 0.024*
C12 0.66455 (10) 0.6481 (2) 0.11624 (10) 0.0207 (3)
C13 0.74188 (9) 0.6910 (2) 0.17902 (11) 0.0209 (3)
C14 0.73261 (9) 0.7221 (2) 0.26399 (10) 0.0214 (3)
H14 0.784233 0.745257 0.308495 0.026*
C15 0.65004 (10) 0.7203 (2) 0.28530 (10) 0.0209 (3)
H15 0.645691 0.746403 0.343561 0.025*
C16 0.15256 (9) 0.8146 (2) 0.21697 (10) 0.0189 (3)
H16A 0.181891 0.901023 0.184356 0.023*
H16B 0.112438 0.883870 0.246167 0.023*
C17 0.04345 (10) 0.5584 (2) 0.19292 (11) 0.0239 (3)
H17A 0.083930 0.480001 0.233581 0.036*
H17B 0.005840 0.485584 0.147187 0.036*
H17C 0.005735 0.625112 0.224820 0.036*
C18 0.14978 (10) 0.5927 (2) 0.09690 (10) 0.0217 (3)
H18A 0.180231 0.681185 0.067531 0.033*
H18B 0.110018 0.519481 0.052959 0.033*
H18C 0.194055 0.515220 0.133985 0.033*
O7 0.06716 (7) 0.31052 (18) 0.59633 (8) 0.0300 (3)
O8 0.10530 (7) 0.53271 (16) 0.52423 (7) 0.0242 (3)
O9 0.06919 (7) 0.27676 (18) 0.45887 (8) 0.0297 (3)
N3 0.08034 (7) 0.37109 (18) 0.52690 (9) 0.0213 (3)

1 Source of materials

All reagents and chemicals were purchased from commercial sources and used without further purification. The 8-((dimethylamino)methyl)-7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one was synthesized via a Mannich reaction. In a typical experiment a formaldehyde solution (10 mL, 37 %), dimethylamine water solution (30 mL, 40 %) and daidzein (6.4 g, 0.025 mol) were added to ethanol (350 mL, 99 %) and stirred for 2 h at 328 K. After cooling, most of the volatile solvents were removed under vacuum on a rotatory evaporator at 308 K. After cooling for 30 min, the mixture was filtered and the residue was washed with water. Then the residue was dried at 383 K. The crude product (4.3 g) was obtained. The crude product was purified by thin layer chromatography (DMSO as solvent, CHCl3–CH3OH = 1:1, v/v). 8-((dimethylamino)methyl)-7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one was obtained. A mixture of Mannich base described before (0.016 g), sodium nitrite (0.041 g), 6 mol/L nitric acid (0.50 mL) and water (8 mL) was sealed in a 20 mL vial and stood for 10 min. The mixture was sonicated for 1 min. The colour of the mixture turned to green. Then the mixture was heated at 363 K for 3 h. Yellow needle crystals of 1-(7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)-N,N-dimethylmethanaminium nitrate were obtained. 1H NMR (400 MHz, DMSO-d 6 ) δ: 11.83 (s, 1H, H4), 11.19 (s, 1H, H1), 8.53 (s, 1H,H9), 8.16 (d, J = 2.1 Hz, 1H, H11), 8.10 (d, J = 8.9 Hz, 1H,H3), 7.75 (dd, J = 8.7, 2.1 Hz, 1H, H15), 7.21 (d, J = 8.7 Hz, 1H, H14), 7.14 (d, J = 8.9 Hz, 1H, H2), 4.45 (s, 2H, H16A, H16B), 2.85 (s, 6H, H18A, H18B, H18C, H17A, H17B, H17C).13C NMR (100 MHz, DMSO-d6) δ:174.76(C7), 162.52(C1), 156.62(C5), 154.17(C9), 152.32(C13), 137.02(C12), 135.93(C15), 129.25(C10), 125.73(C3), 123.17(C8), 122.06(C11), 119.45(C14), 116.94(C4), 115.11(C6), 104.77(C2), 49.37(C16), 43.26(C17, C18). IR spectra (potassium bromide pellet) were recorded on a Nicolet 6700. IR (v/cm−1): 3286, 3089, 1646, 1626, 1600, 1536, 1469, 1430, 1385, 1311, 1220, 1163, 1138, 1083, 1048, 1037, 1000, 970, 951, 924, 892, 862, 848, 806, 798, 779, 763, 752, 706, 658, 641, 578, 558, 538.

2 Experimental details

Carbon-bound H atoms were placed in calculated positions and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2 Ueq(C). The oxygen-bound and nitrogen-bound H atoms were located on a difference Fourier map.

3 Comment

In the past decades, much attention has been focused on the nitration of flavonoids [5], [6], [7], [8]. Some of nitro derivatives of flavonoids possess important biological activities. Our previous investigations showed that Daizein Mannich base derivatives of amino acid react with nitrating agent [9, 10]. To extend this research, we used the Daizein Mannich base derivative of an aliphatic amine to react with a nitrating agent and got the title compound. In this study, the title compound was obtained from 8-((dimethylamino)methyl)-7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one via a nitration substitution reaction.

The title compound contains one cation and one nitrate ion in the asymmetric unit (cf. the figure). The bond distances and bond angles are in normal ranges [9, 10]. The dihedral angle between planar rings B (C10–C15) and C (C7–C9/O3/C5/C4) is 34.05°. The nitrogen atom N1 is protonated. The molecule shows an intramolecular O4–H4⃛O5 hydrogen bond of length 1.922 Å. There exist various O–H⃛O and N–H⃛O hydrogen bonds. There are π⃛π stacking interactions between C1–C6 phenyl rings and C10–C15 phenyl rings from adjacent compounds. The centroid-centroid distance is 3.78 Å. Together with hydrogen bonds interactions and π⃛π stacking interactions a three-dimensional network is obtained.

Corresponding author: Dong-Mei Yao, School of Chemical and Biological Engineering, Hechi University, Yizhou District, Hechi, Guangxi, 546300, P.R. China, E-mail:

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

  2. Research funding: Guangxi Natural Science Foundation of China (No. 2020GXNSFBA297138) and 2021 High-level Talents Scientific Research Startup Fund of Hechi University (No. 2021GCC021).

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

References

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Received: 2023-06-21
Accepted: 2023-07-19
Published Online: 2023-08-01
Published in Print: 2023-10-26

© 2023 the author(s), published by De Gruyter, Berlin/Boston

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

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https://doi.org/10.1515/ncrs-2023-0294
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of (N-([1,1′:4′,1″-terphenyl]-4,4′-diethyl)-2-(bis(pyridin-2-ylmethyl)amino)acetamide-κ4N,N,N″, O)tri(nitrato-kO, O′) samarium(III) - methanol - acetonitrile (1/1/1), C40H39SmN8O14
  4. The crystal structure of 6,6′-(((2-(dimethylamino)ethyl)azanediyl)bis(methylene))bis(2-chloro-4-methyl phenolate-κ4N,N′,O,O′)-(pyridine-2,6-dicarboxylato-N,O,O′)-titanium(IV), C27H27Cl2N3O6Ti
  5. N′-[(1E)-(4–Fluorophenyl)methylidene]adamantane-1-carbohydrazide, C18H21FN2O
  6. Crystal structure of 4-bromo-3-nitro-1H-pyrazole-5-carboxylic acid monohydrate, C4H2N3BrO4·H2O
  7. Crystal structure of dipyridine-k1N-tris(2,2,6,6-tetramethyl-5-oxohept-3-en-3-olato-k2O,O′)dysprosium(III), DyC43H67O6N2
  8. Crystal structure of cyclo[tetraiodido-bis{μ2-1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-isopropyl-imidazol)-k2N:N}dicadmiun(II)], C26H30N10Cd2I4
  9. The crystal structure of tert-butyl (E)-3-(2-(benzylideneamino)phenyl)-1H-indole-1-carboxylate, C26H24N2O2
  10. The crystal structure of 4-(3-carboxy-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4- dihydroquinolin-7-yl)-2-methylpiperazin-1-ium 2,5-dihydroxybenzoate methanol solvate, C27H32FN3O9
  11. Crystal structure of (μ2-1-(4,4′-bipyridine-κ2N:N′)-bis[diaqua-(4-iodopyridine-2,6-dicarboxylato-κ3O,N,O′)–cobalt(II)], C24H20Co2I2N4O12
  12. The crystal structure of dimethyl 4,4′-(10,20-diphenylporphyrin-5,15-diyl)dibenzoate dichloromethane solvate, C49H36N4O4Cl2
  13. (E)-2-((E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-ylidene)hydrazine-1-carbothioamide C14H23N3S1
  14. The crystal structure of [1-(4-(trifluoromethyl)phenyl)-3,4-dihydroquinolin-2(1H)-one], C16H12F3NO
  15. Crystal structure of (E)-2-amino-N′-((3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methylene)benzohydrazide – dimethylformamide – water (1/1/2), C15H16N4O3·C3H7NO·2H2O
  16. Crystal structure of 3-(4-bromophenyl)-5-methyl-1H-pyrazole, C10H9BrN2
  17. Crystal structure of 1,10-phenanthrolinium bromide dihydrate, C12H9N2Br
  18. Crystal structure of N-(4′-chloro-[1,1′-biphenyl]-2-yl)formamide, C13H10ClNO
  19. The crystal structure of nitroterephthalic acid, C8H5NO6
  20. Crystal structure of (2-((4-bromo-2,6-dichlorophenyl)amino)phenyl) (morpholino)methanone, C17H15BrCl2N2O2
  21. Crystal structure of tetraaqua-bis(ethanol-κO)-tetrakis(μ2-trifluoroacetate-κ2O:O′)-bis(trifluoroacetate-κ2O)digadolinium(III) Gd2C16H20O18F18
  22. The crystal structure of dimethyl 4,4′-[10,20-bis(2,6-difluorophenyl)porphyrin-5,15-diyl]dibenzoate chloroform solvate, C50H32Cl6F4N4O4
  23. The crystal structure of N,N′-((nitroazanediyl)bis(methylene))diacetamide, C6H12O4N4
  24. The crystal structure of [bis(2,2′-bipyridine-6-carboxylato-κ3N,N,O)magnesium(II)]dihydrate, C22H18N4O6Mg
  25. Crystal structure of poly[diaqua-(bis(μ2-1,4-bis(imidazol-1-ylmethyl)benzene)-κ2N,N′] cobalt(II)-tetraqua-bis(1,4-bis(imidazol-1-ylmethyl)benzene)-κ1N)-cobalt(II) di(2,5-thiophenedicarboxylate) dihydrate, C68H76Co2N16O16S2
  26. Crystal structure of poly[chlorido-μ2-chlorido-(μ2-1-[(2-ethyl-4-methyl-1H-imidazol-1-yl)methyl]-1H-benzotriazole-κN:N’)cadmium(II)], C13H15CdN5Cl2
  27. The crystal structure of (4-hydroxybenzenesulfonate)-k1O-6,6′-((1E,1′E)- (ethane-1,2-diylbis(azaneylylidene))bis(methaneylylidene)) bis(2-methoxyphenol)-κ2N,N,μ2O,O,κ2O, O)-(methanol)-cobalt(II) sodium(I), C25H27CoN2NaO9S
  28. Crystal structure of (1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)(4-((2-methyl-6-(trifluoromethyl)pyrimidin-4-yl)amino)piperidin-1-yl)methanone, C17H18F6N6O
  29. Crystal structure of bis{[(cyclohexylimino)(phenylimino)-l5-(methyl)diethylazane-κ2N:N′]-(ethyl)-zinc(II)]}, C38H62N6Zn2
  30. Crystal structure of 2-[(4-bromobenzyl)thio]-5-(5-bromothiophen-2-yl)-1,3,4-oxadiazole, C13H8Br2N2OS2
  31. Crystal structure of 10-methoxy-7,11b,12,13-tetrahydro-6H-pyrazino [2′,3′:5,6]pyrazino[2,1-a]isoquinoline, C15H16N4O
  32. The crystal structure of 1-propyl-2-nitro-imidazole oxide, C6H9N3O3
  33. The crystal structure of 3-nitrobenzene-1,2-dicarboxylic acid–2-ethoxybenzamide (1/1), C17H16N2O8
  34. The structure of RUB-1, (C8H16N)6[B6Si48O108], a boron containing levyne-type zeolite, occluding N-methyl-quinuclidinium in the cage-like pores
  35. The crystal structure of diaqua-(naphthalene-4,5-dicarboxylate-1,8-dicarboxylic anhydride-κ1O)-(4′-(4-(1H-benzimidazolyl-1-yl)phenyl)-2,2′:6′,2″-terpyridine-κ3N,N′,N″)–manganese(II) dihydrate, C42H27MnN5O9·2H2O
  36. Crystal structure of 6,6′-((1E,1′E)-hydrazine-1,2-diylidenebis(methanylylidene))bis (3-(3-bromopropoxy)phenol), C20H22Br2N2O4
  37. The crystal structure of 3-(2-hydroxyphenyl)-4-phenyl-6-(p-tolyl)-2H-pyran-2-one, C24H18O3
  38. Crystal structure of bis(μ2-2-(1,5-dimethyl–3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino)methyl)phenolato-κ4O:O,N,O′)-(nitrato-κ2O,O′)dicobalt(II), C36H32Co2N8O4
  39. Synthesis and crystal structure of (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexadecahydro-3H-cyclopenta[α] phenanthren-3-one O-(4-fluorobenzoyl) oxime, C28H36FNO2
  40. The crystal structure of 4-aminiumbiphenyl benzenesulfonate, C18H17NO3S
  41. Synthesis and crystal structure of 1-(7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)-N,N-dimethylmethanaminiumnitrate, C18H17N3O9
  42. Crystal structure of N-(Ar)-N′-(Ar′)-formamidine, C14H12Br2N2O
  43. The crystal structure of 4-(2,4-dichlorophenyl)-2-(4-fluorophenyl)-5-methyl-1H-imidazole, C16H11Cl2FN2
  44. Crystal structure of 1-(4–chlorophenyl)-4-benzoyl-3-methyl-1H-pyrazol-5-ol, C17H13ClN2O2
  45. The crystal structure of 5-amino-1-methyl-4-nitroimidazole, C4H6O2N4
  46. Crystal structure of 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene-N,N′-bis(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-1,3,2-diazaborol-2-yl)-l2-germenediamine, C63H94B2GeN8
  47. The crystal structure of (bromido, chlorido)-tricarbonyl-(5,5′-dimethyl-2,2′-bipyridine)-rhenium(I), C15H12Br0.2Cl0.8N2O3Re1
  48. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-bis(propan-2-yl)-1H-pyrazol-4-amine, C26H36N6
  49. The crystal structure of poly[2-(4-carboxypyridin-3-yl)terephthalpoly[diaqua-(μ4-2-(6-carboxylatopyridin-3-yl)terephthalato-κ5O,N:O′:O″,O‴)]) cadmium(II)] dihydrate, C28H20Cd3N2O16
  50. Crystal structure of [tetraaqua-bis((3-carboxy-5-(pyridin-4-yl)benzoate-κ1N)cobalt(II)] tetrahydrate, C26H32CoN2O16
  51. Crystal structure of bis(μ2-azido-κ2N:N)-tetrakis(azido-κ1N)-tetrakis(1,10-phenanthroline-κ2N,N′)dibismuth(III), C48H32N26Bi2
  52. Crystal structure of (Z)-N-(4-(4-(4-((4,5,6-trimethoxy-3-oxobenzofuran-2(3H)-ylidene)methyl)phenoxy)butoxy)phenyl)acetamide, C30H31NO8
  53. Crystal structure of poly[diaqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-bis(μ2-5-carboxybenzene-1,3-dicarboxylato-O,O′:O″)-aqua-di-zinc dihydrate solvate], C27H28N4O16Zn2
  54. Crystal structure of 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile, C12H14N2
  55. Crystal structure of chlorido-(5-nitro-2-phenylpyridine-κ2N,C)-[(methylsulfinyl)methane-κ1S]platinum(II), C13H13ClN2O3PtS
  56. The crystal structure of the co-crystal 1,4-dioxane–4,6-bis(nitroimino)-1,3,5-triazinan-2-one(2/1), C11H19N7O9
  57. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-dimethyl-1H-pyrazol-4-amine di-methanol solvate, C18H20N6·2(CH3OH)
  58. Crystal structure of catena-poly[bis(μ2-azido-k2N:N′)-(nitrato-K2N:N′)-bis(1,10-phenanthroline-K2N:N′)samarium(III)], C24H16N11O3Sm
  59. Crystal structure of (Z)-2-(4-((5-bromopentyl)oxy)benzylidene)-4,5,6-trimethoxybenzofuran-3(2H)-one, C23H25BrO6
  60. Crystal structure of bis(3,5-dimethyl-1H-pyrazol-4-ammonium) tetrafluoroterephthate, 2[C5H10N3][C8F4O4]
  61. Crystal structure of 2-amino-4-(2-fluoro-4-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  62. Crystal structure of 6-(pyridin-3-yl)-1,3,5-triazine-2,4-diamine-sebacic acid (2/1), C13H17N6O2
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