Home Crystal structure of 9-methoxy-4-(2-methoxypyridin-3-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine C19H18N4O2
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Crystal structure of 9-methoxy-4-(2-methoxypyridin-3-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine C19H18N4O2

  • Mei-Lin Song , Xian-Rui Xie and Gui-Ge Hou ORCID logo EMAIL logo
Published/Copyright: February 11, 2025
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 240 Issue 2

Abstract

C19H18N4O2, triclinic, P1¯ (no. 2), a = 8.3712(10) Å, b = 9.6699(11) Å, c = 10.5323(12) Å, α = 77.24(1)°, β = 74.576(10)°, γ = 81.126(9)°, V = 797.42(17) Å3, Z = 2, R gt (F) = 0.0564, wR ref (F2) = 0.1540, T = 293.0 K.

CCDC no.: 2283207

The crystal structure is shown in the figure. Displacement ellipsoids are drawn at the 30 % probability level.

Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Yellow block
Size: 0.16 × 0.14 × 0.10 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.09 mm−1
Diffractometer, scan mode: SuperNova, AtlasS2, CCD plate
θmax, completeness: 25.5°, 100 %
N(hkl)measured, N(hkl)unique, Rint: 6079, 2961, 0.041
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 2,206
N(param)refined: 230
Programs: Rigaku 1 , SHELX 2 , 3
Table 2:

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

x y z Uiso*/Ueq
C1 0.3956 (3) 0.9973 (2) 0.21818 (19) 0.0200 (5)
C2 0.3075 (2) 0.7772 (2) 0.24523 (19) 0.0181 (5)
C3 0.2370 (2) 0.7765 (2) 0.37988 (19) 0.0192 (5)
C4 0.2532 (2) 0.8976 (2) 0.42677 (19) 0.0191 (5)
C5 0.1466 (3) 0.6558 (2) 0.4754 (2) 0.0246 (5)
H5A 0.101142 0.605208 0.425233 0.030*
H5B 0.225046 0.589204 0.517401 0.030*
C6 0.0070 (3) 0.7099 (2) 0.5827 (2) 0.0258 (5)
H6A −0.085625 0.753961 0.543717 0.031*
H6B −0.031308 0.629818 0.652281 0.031*
C7 0.0587 (3) 0.8162 (2) 0.6448 (2) 0.0222 (5)
C8 −0.0170 (3) 0.8337 (2) 0.7755 (2) 0.0248 (5)
H8 −0.094148 0.771975 0.828461 0.030*
C9 0.0186 (3) 0.9392 (2) 0.8290 (2) 0.0256 (5)
H9 −0.035046 0.948841 0.916504 0.031*
C10 0.1350 (3) 1.0317 (2) 0.75196 (19) 0.0240 (5)
C11 0.2157 (3) 1.0152 (2) 0.62286 (19) 0.0215 (5)
H11 0.296713 1.074437 0.572236 0.026*
C12 0.1759 (2) 0.9096 (2) 0.56801 (19) 0.0189 (5)
C13 0.2970 (2) 0.6602 (2) 0.17671 (19) 0.0187 (5)
C14 0.3654 (2) 0.5195 (2) 0.21249 (19) 0.0194 (5)
C15 0.2906 (3) 0.4468 (2) 0.0471 (2) 0.0251 (5)
H15 0.288513 0.374302 0.002507 0.030*
C16 0.2189 (3) 0.5795 (2) 0.0037 (2) 0.0252 (5)
H16 0.168114 0.596534 −0.067513 0.030*
C17 0.2239 (3) 0.6885 (2) 0.06883 (19) 0.0232 (5)
H17 0.178258 0.780370 0.040048 0.028*
C18 0.4981 (3) 0.3461 (2) 0.3597 (2) 0.0315 (6)
H18A 0.409772 0.287311 0.375098 0.047*
H18B 0.532394 0.337267 0.441384 0.047*
H18C 0.590830 0.316120 0.292026 0.047*
C19 0.2489 (3) 1.2497 (3) 0.7300 (2) 0.0340 (6)
H19A 0.361421 1.213836 0.693493 0.051*
H19B 0.249109 1.319185 0.782477 0.051*
H19C 0.196383 1.293337 0.658162 0.051*
N1 0.3330 (2) 1.00667 (17) 0.34736 (16) 0.0200 (4)
N2 0.3849 (2) 0.88611 (17) 0.16227 (16) 0.0199 (4)
N3 0.4750 (2) 1.10602 (19) 0.13626 (17) 0.0264 (5)
H3B 0.522919 1.100204 0.052174 0.034 (7)*
H3A 0.466399 1.188337 0.165583 0.034 (7)*
N4 0.3639 (2) 0.41487 (18) 0.15057 (16) 0.0221 (4)
O1 0.44040 (18) 0.49199 (15) 0.31557 (14) 0.0251 (4)
O2 0.1593 (2) 1.13532 (17) 0.81280 (14) 0.0319 (4)

1 Source of material

Referring to the synthesis technique, 4 , 5 a 20 % sodium hydroxide solution (5.0 mL) was used as a catalyst. 7-Methoxy-3,4-dihydronaphthalen-1(2H)-one (0.70 g, 4.00 mmol) and 2-methoxynicotinaldehyde (0.55 g, 4.00 mmol) were dissolved in 25 mL of methanol and mixed by a Claisen–Schmidt condensation reaction at room temperature for 3 h, resulting in a yellow precipitate. The intermediate was filtered to obtain (E)-7-methoxy-2-((2-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one. The intermediate (0.52 g, 1.76 mmol), guanidine hydrochloride (0.50 g, 5.28 mmol), and potassium hydroxide (0.30 g, 5.28 mmol) were dissolved in a solution of 15 mL ethanol and 15 mL dichloroethane. The mixture was stirred at 85 °C for 2 h and then filtered. After removing the solvent by concentrating under reduced pressure, 15 mL of ethanol and 5 mL of concentrated ammonia water were added at room temperature to eliminate hydrogen chloride. The mixture was extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, filtered, and the residue was dissolved in a mixture of dichloromethane and methanol (2:1, v/v). The product was then recrystallized using a solvent.

2 Experimental details

The H atoms were placed in idealized positions and treated as riding on their parent atoms, with d(C–H) = 0.96 Å (methyl), Uiso(H) = 1.5Ueq(C), and d(C–H) = 0.97 Å (methylene), Uiso(H) = 1.2Ueq(C) and d(C–H) = 0.98 Å (methyne), Uiso(H) = 1.2Ueq(C), and d(C–H) = 0.93 Å (aromatic), Uiso(H) = 1.2Ueq(C) H atoms on N atom were located in difference maps and treated as riding.

3 Comment

3,4-Dihydronaphthalen-1(2H)-one derivatives have been studied for their antitumor and anti-inflammatory activity, as well as their potential as regulators of allergy and inflammatory reactions. They have also been investigated as potential inhibitors of retinoic acid metabolism enzymes and have shown promise in the treatment of skin diseases and cancer. 6 , 7 , 8 , 9 However, 3,4-dihydronaphthalen-1(2H)-one derivatives have poor solubility in water. The water solubility and biological activity of 3,4-dihydronaphthalen-1(2H)-one derivatives can be further improved through the Michael addition reaction of their α, β-unsaturated ketones with guanidine hydrochloride. This study utilizes 7-methoxy-3,4-dihydronaphthalen-1(2H)-one as a starting material. The starting material underwent a Claisen–Schmidt condensation reaction with 2-methoxynicotinaldehyde to produce the intermediate (E)-7-methoxy-2-((2-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, which was subsequently condensed with guanidine hydrochloride to yield the desired product: 9-methoxy-4-(2-methoxypyridin-3-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine.

The single crystal structure analysis shows that the crystal belongs to the triclinic crystal system. The central parent nucleus of the compound is 5,6-dihydrobenzo[h]quinazolin-2-amine. Carbon-nitrogen bonds vary in length. i.e. Bond length of C(1)–N(1), C(1)–N(2), C(1)–N(3), C(2)–C(4)–N(1), C(14)–N(4), C(15)–N(4) are 1.339(3), 1.360(3), 1.342(3), 1.340(2), 1.338(3), 1.323(3), and 1.345(3) Å, respectively. As a result of the 3,4-dihydronaphthalen-1(2H)-one torsion effect, the pyridine ring is not coplanar with the central mother nucleus, with a dihedral angle of approximately 65.4°. This distorted structure may increase the likelihood of interacting with biologically active molecules. 10 , 11 Notably, the N atom in the cross section of our pyridine ring, which can act as a hydrogen bond donor, forms the foundation for increased biological activity (cf. the Figure). The bond lengths and angles were within the expected range. 12 , 13

Corresponding author: Gui-Ge Hou, School of Pharmacy, Binzhou Medical University, Yantai, 264003, P.R. China, E-mail:

Acknowledgments

This work was supported by Shandong Provincial Natural Science Foundation (No. ZR2023MH190).

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Received: 2024-12-25
Accepted: 2025-01-27
Published Online: 2025-02-11
Published in Print: 2025-04-28

© 2025 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-2024-0486
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of N-(3-bromo-4-fluorophenyl)-N′-hydroxy-4-{[2-(4-methylphenyl)ethyl]amino}-1,2,5-oxadiazole-3-carboximidamide, C18H17BrFN5O2
  4. Synthesis and crystal structure of ethyl (2S,4aS,6aS,6bR,8aR,12aS,12bR,14bR,E)-10-(((3,4-dichlorobenzyl)oxy)imino)-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate
  5. The crystal structure of pyrazole nitrate
  6. Crystal structure of tetramethyl-bis(μ2-2-(2-hydroxy-3-methoxybenzylidene)-1-(6-(2-(2-hydroxy-3-methoxybenzylidene)hydrazine-1-carbonyl)picolinoyl)hydrazin-1-ido-κ4O,N,O′:O′)ditin(II) ─ ethanol (1/2), C54H62N10O14Sn2
  7. Crystal structure of catena-poly[μ3-iodido-(4-bromopyridine-κ1N)copper(I)], C5H4BrNCuI
  8. The crystal structure of cyclopentadienyl Co–P–C complexes by benzylideneacetone addition, C38H38CoO2P
  9. Synthesis and crystal structure of-(3S,10S,13S,17S)-N-(2-methoxyphenyl)-10,13-dimethyl-17-((R)-1-(phenylamino)ethyl)hexadecahydro-1H-cyclopenta[α]phenanthren-3-amine, C34H48N2O
  10. The crystal structure of (E)-3-((E)-3-(4-ethoxy-3-methoxyphenyl)-1-hydroxyallylidene) chroman-2,4-dione, C21H18O6
  11. The crystal structure of trans–L/D-[bis-(2-methyl-8-hydroxyquinoline-κ2 N,O) bis-(1,3,5-triaza-7-phosphaadamantane-κ2 P)cobalt(III)] tetrafluoroborate
  12. Crystal structure of 9-chloro-2,3,4,4a,5,6-hexahydro-1H-pyrido [1′,2′:1,6]pyrazino[2,3-b]quinoxaline, C14H15ClN4
  13. Crystal structure of 7-(diethylamino)-3-(benzoyl)-2 H -chromen-2-one, C20H19NO3
  14. The crystal structure of 4–bromo-3,5-dinitropyrazole
  15. Crystal structure of 8-hydroxy-3,5,8a-trimethyl-7,8,8a,9-tetrahydronaphtho[2,3-b]furan-4,6-dione, C15H16O4
  16. Crystal structure of 5-hydroxy-3,5,8a-trimethyl-4a,5,6,7,8a,9-hexahydronaphtho[2,3-b]furan-4,8-dione, C15H18O4
  17. Synthesis and crystal structure of-(3S,10S,13S,17S)-N-(2-methoxyphenyl)-10,13-dimethyl-17-((R)-1-(p-tolylamino)ethyl)hexadecahydro-1H-cyclopenta[α]phenanthren-3-amine, C35H50N2O
  18. The crystal structure of catena-poly((μ2-1,3,5-tri(1H- imidazol-1-yl)benzene κ2N:N′)-bis(4-hydroxbenzoato-κ1O)-zinc(II) monohydrate), C29H24N6O7Zn
  19. Crystal structure of 2-(benzo[d]oxazol-2-yl)acetonitrile, C9H6N2O
  20. Crystal structure of 1,3-dihydroxy-6,8-dimethoxy-2-(6-methyltetrahydro-2Hpyran-2-yl)-4a,9a-dihydroanthracene-9,10-dione, C22H22O7
  21. The crystal structure of the double salt potassium 1-methylpiperazine-1,4-di-ium trinitrate, C5H14KN5O9
  22. Crystal structure of 5′-hydroxy-6′-methoxy-1′-methyl-2′,3′,8′,8a′-tetrahydro-1′H-spiro[cyclohexane-1,7′-cyclopenta[ij]isoquinoline]-2,5-dien-4-one, C18H19NO3
  23. The crystal structure of 1,1′-(2,3,5,6-tetramethylpyrazine-1,4-diyl)bis(ethan-1-one), C12H18N2O2
  24. Crystal structure of [μ2-piperazine-1,4-bis(2-hydroxypropanesulfonato-κ2O:O′)] bis(μ2-4,4′-trimethylenedipyridyl-κ2N:N′)disilver(I), C18H24AgN3O4S
  25. Crystal structure of bis ((1-((E)-((4-methoxyphenyl)imino)methyl)naphthalen-2-yl)oxy) copper(II), C36H28CuN2O4
  26. Synthesis and crystal structure of 6,6′-((1E,11E)-5,8-dioxa-2,11-diazadodeca-1,11-diene-1,12-diyl) bis(2,4-di-tert-butylphenol), C36H56N2O4
  27. The crystal structure of barium hexahydroxidoiridate(IV) dihydroxide, Ba2[Ir(OH)6](OH)2
  28. Crystal structure of cinnamoyl ferrocene, C19H16FeO
  29. Crystal structure of (E)-3-(4-butoxyphenyl)acryloylferrocene, C23H24FeO2
  30. Crystal structure of 7-(dimethylamino)-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-ethyl carboxylate, C15H16F3NO4
  31. The crystal structure of 1-phenylethan-1-aminium 4-hydroxy-3,5-dimethoxybenzoate C17H21NO5
  32. The crystal structure of 1,3,5-trichloro-2-nitrobenzene
  33. The crystal structure of tris(μ2-bromido)-bis(η6-p-cymene)-diosmium(II) tetrafluoroborate, C20H28BBr3F4Os2
  34. Crystal structure of new barium lithium manganese fluorides: Ba14Li1.87Mn14.13F68 with a Jarlite–related structure
  35. Crystal structure of (4-fluorobenzyl)triphenylphosphonium chloride, C25H21ClFP
  36. The crystal structure of calcitriol–chloroform (1/1), C27H44O3⋅CHCl3
  37. The crystal structure of (E)-1-((3)-nitrophenyl)pyren-3-(pyren-1-yl)prop-2-en-1-one, C25H15NO3
  38. Crystal structure of (E)-2-hydroxy-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H16N2O3
  39. Crystal structure of (E)-(3-(thiophen-2-yl)acryloyl)ferrocene, C17H14FeOS
  40. Crystal structure of (E)-(3-(furan-2-yl)acryloyl)ferrocene, C17H14FeO2
  41. Synthesis and crystal structure poly[diaqua(μ3-3-(((7-hydroxy-3-(4-methoxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl) methyl)ammonio)propanoate-κ3 O:O′:O″) sodium(I)] monohydrate, C20H24NNaO12S
  42. Crystal structure of 9-methoxy-4-(2-methoxypyridin-3-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine C19H18N4O2
  43. Synthesis and crystal structure of 4-(difluoromethyl)-1-methyl-N-(pyridin-3-yl)-1H-pyrazole-3-carboxamide hydrate, C11H12F2N4O2
  44. The crystal structure of caesalfurfuric acid B, C22H32O4
  45. The crystal structure of 2-bromo-2-(5-bromo-2-methyl-4-nitro-1H-imidazol-1-yl)-1-phenylethanone, C12H9Br2N3O3
  46. The crystal structure of bis{chlorido-[μ2-(1-oxidopyridin-2-yl)(pyridin-2-yl)amido-κ3 O,N, N′]copper(II)}, C20H16Cl2Cu2N6O2
  47. The crystal structure of 3-amino-2-formyl-1-phenyl-9,10-dihydrophenanthrene-4-carbonitrile, C22H16N2O
  48. The crystal structure of 1,1′-(2,5-dimethylpyrazine-1,4-diyl)bis(ethan-1-one), C10H14N2O2
  49. Crystal structure of 5′-(9-phenyl-9H-carbazol-3-yl)-[2,2′-bithiophene]-5-carbaldehyde, C27H17NOS2
  50. The crystal structure of the double salt dipyridin-1-ium bromide tribromide
  51. Crystal structure of (E)-(3-(3-methylthiophen-2-yl)acryloyl)ferrocene, C18H16FeOS
  52. Crystal structure of (E)-(3-(4-phenoxyphenyl)acryloyl)ferrocene, C25H20FeO2
  53. Crystal structure of (E)-(3-(3,4-dimethylphenyl)acryloyl)ferrocene, C21H20FeO
  54. Crystal structure of [(1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N‴)tetracyanidodiplatinum(II)] dimethyl sulfoxide solvate, C18H36N8O2Pt2S2
  55. Crystal structure of (4-ethoxybenzyl)triphenylphosphonium bromide ethanol solvate, C29H32BrO2P
  56. Crystal structure of (1-naphthalen-1-yl-methyl)triphenylphosphonium chloride ethanol solvate, C31H30ClOP
  57. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)platinum(II) bis[tribromido(dimethyl sulfoxide-κS)platinate(II)], C14H36Br6N4O2Pt3S2
  58. Crystal structure of (2-methylbenzyl)triphenylphosphonium chloride ethanol solvate, C28H30ClOP
  59. Crystal structure of bis(η2, σ1-8-methoxycyclooct-4-enyl)(μ2-1,4,8,11-tetraazacyclotetradecane-κ4 N, N′, N″, N‴)diplatinum(II) dibromide, C28H54Br2N4O2Pt2
  60. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) tetrabromidopalladate(II), C10H24Br4N4Pd2
  61. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) bis[trichlorido(dimethyl sulfoxide-κS)platinate(II)], C14H36Cl6N4O2PdPt2S2
  62. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) tetraiodidopalladate(II), C10H24I4N4Pd2
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