Home Physical Sciences Crystal structure of 4-chlorobenzyl (S)-2-(6-methoxynaphthalen-2-yl)propanoate, C21H19ClO3
Article Open Access

Crystal structure of 4-chlorobenzyl (S)-2-(6-methoxynaphthalen-2-yl)propanoate, C21H19ClO3

  • Fei Li , Ji-Xiang Xiao and Li-Na Gao ORCID logo EMAIL logo
Published/Copyright: August 7, 2024

Abstract

C21H19ClO3, orthorhombic, P212121 (no. 19), a = 6.0384(3) Å, b = 11.5696(7) Å, c = 24.6624(14) Å, V = 1722.96(17) Å3, Z = 4, Rgt(F) = 0.0253, wRref(F2) = 0.0637, T = 100(2) K.

CCDC no.: 2371430

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: 0.12 × 0.11 × 0.10 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.24 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 27.5°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 38,454, 3,941, 0.034
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 3,775
N(param)refined: 228
Programs: Bruker, 1 Olex2, 2 SHELX 3
Table 2:

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

Atom x y z Uiso*/Ueq
C1 0.2270 (3) 1.04625 (15) 0.28766 (7) 0.0194 (3)
C2 0.4274 (3) 1.07362 (15) 0.31135 (7) 0.0219 (3)
H2 0.484060 1.150126 0.309559 0.026*
C3 0.5447 (3) 0.98697 (15) 0.33790 (7) 0.0210 (4)
H3 0.683023 1.004660 0.354244 0.025*
C4 0.4622 (3) 0.87454 (14) 0.34089 (7) 0.0182 (3)
C5 0.2588 (3) 0.84995 (15) 0.31706 (7) 0.0204 (3)
H5 0.200330 0.773837 0.319115 0.024*
C6 0.1400 (3) 0.93574 (15) 0.29025 (7) 0.0211 (3)
H6 0.001262 0.918682 0.273954 0.025*
C7 0.5979 (3) 0.78552 (14) 0.37062 (7) 0.0222 (4)
H7A 0.749753 0.783092 0.355496 0.027*
H7B 0.608188 0.806236 0.409483 0.027*
C8 0.6135 (3) 0.58359 (15) 0.38336 (7) 0.0187 (3)
C9 0.4817 (3) 0.47210 (15) 0.37716 (7) 0.0183 (3)
H9 0.349528 0.478680 0.401387 0.022*
C10 0.3945 (3) 0.45619 (15) 0.31906 (7) 0.0221 (4)
H10A 0.306956 0.523964 0.308637 0.033*
H10B 0.301269 0.386944 0.317409 0.033*
H10C 0.519693 0.447512 0.294101 0.033*
C11 0.6108 (3) 0.36680 (14) 0.39559 (6) 0.0175 (3)
C12 0.5192 (3) 0.29156 (14) 0.43216 (7) 0.0160 (3)
H12 0.378630 0.308901 0.447406 0.019*
C13 0.6289 (3) 0.18849 (14) 0.44783 (6) 0.0145 (3)
C14 0.8407 (3) 0.16267 (14) 0.42529 (6) 0.0141 (3)
C15 0.9335 (3) 0.24205 (14) 0.38758 (6) 0.0165 (3)
H15 1.074708 0.226613 0.372226 0.020*
C16 0.8222 (3) 0.34038 (15) 0.37310 (7) 0.0189 (3)
H16 0.886945 0.391880 0.347634 0.023*
C17 0.5342 (3) 0.10947 (14) 0.48533 (7) 0.0160 (3)
H17 0.393761 0.125906 0.500866 0.019*
C18 0.6424 (3) 0.01022 (14) 0.49937 (7) 0.0162 (3)
H18 0.577241 −0.041597 0.524638 0.019*
C19 0.8519 (3) −0.01570 (14) 0.47628 (7) 0.0157 (3)
C20 0.9503 (3) 0.05846 (13) 0.44007 (6) 0.0145 (3)
H20 1.090792 0.040274 0.424983 0.017*
C21 1.1330 (3) −0.15936 (16) 0.46643 (7) 0.0224 (4)
H21A 1.100377 −0.169301 0.427786 0.034*
H21B 1.177810 −0.233706 0.481993 0.034*
H21C 1.253368 −0.103295 0.470783 0.034*
Cl1 0.08243 (8) 1.15281 (4) 0.25211 (2) 0.02824 (12)
O1 0.4944 (2) 0.67421 (10) 0.36484 (5) 0.0217 (3)
O2 0.7957 (2) 0.59384 (11) 0.40253 (6) 0.0258 (3)
O3 0.9393 (2) −0.11810 (10) 0.49381 (5) 0.0199 (3)

1 Source of material

The compound was obtained commercially (Bide Pharmatech Co., Ltd). Crystals suitable for the diffraction study were taken directly from the provided product.

2 Experimental details

Coordinates of hydrogen atoms were constrained by some AFIX 3 options. The Uiso values were set to be 1.5Ueq of the carrier atom for methyl and 1.2Ueq for remaining H atoms.

3 Comment

Naproxen, a potent non-steroidal anti-inflammatory drug (NSAID), blocks the activity of both COX-1 and COX-2 enzymes, which are key components of the cyclooxygenase pathway. Naproxen commonly causes gastrointestinal reactions, such as gastrointestinal bleeding. 1 These side effects may be linked to the carboxyl group present in naproxen. Esterifying the carboxyl group has been shown to reduce these side effects. 2 , 3 Currently, naproxen is used clinically to treat or alleviate inflammation and pain caused by various conditions such as rheumatoid arthritis 4 and gout. 5 Additionally, naproxen has been found to exhibit many interesting applications. 6 , 7 , 8 Therefore, the development of naproxen derivatives with fewer side effects is of significant importance.

The title compound contains one naphthyl ring and one phenyl ring. The bond distances of C–O are 1.439(2) Å (C7–O1), 1.204(2) Å (C8–O2),1.3671(19) Å (C19–O3), 1.432(2) Å (C21–O3) and 1.351(2) Å (C8–O1). The bond distance of C8–O2 are shorter than others, indicating a double bond. The bond of C–Cl is 1.7466(17) Å (C1–Cl1). The dihedral angels of ring 1 (C1–C2–C3–C4–C5–C6) and ring 2 (C11–C12–C13–C14–C15–C16), ring 1 (C1–C2–C3–C4–C5–C6) and ring 3 (C14–C13–C17–C18–C19–C20), and ring 2 (C11–C12–C13–C14–C15–C16) and ring 3 (C14–C13–C17–C18–C19–C20) are 58.82(7)°, 56.88(7)° and 0.90(6)°. The other bond distances and angles are in their normal ranges according to the previously reported compounds. 9 , 10


Corresponding author: Li-Na Gao, The Second Hospital of Jilin University, Changchun 130000, China, 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 statement: The authors declare no conflicts of interest regarding this article.

References

1. Bruker. SAINT and SADABS; Bruker AXS Inc.: Madison, Wisconsin, USA, 2000.Search in Google Scholar

2. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. OLEX2: A Complete Structure Solution, Refinement and Analysis Program. J. Appl. Crystallogr. 2009, 42, 339–341; https://doi.org/10.1107/s0021889808042726.Search in Google Scholar

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

4. Huang, Z. J.; Carlos, A. V.; Khaled, R. A. A.; Morshed, A. C.; Julie, A. R.; Jenna, F. D.; Bruce King, S.; Edward, E. K. Ethanesulfohydroxamic Acid Ester Prodrugs of Nonsteroidal Anti-inflammatory Drugs (NSAIDs): Synthesis, Nitric Oxide and Nitroxyl Release, Cyclooxygenase Inhibition, Anti-inflammatory, and Ulcerogenicity Index Studies. J. Med. Chem. 2011, 54, 1356–1364; https://doi.org/10.1021/jm101403g.Search in Google Scholar PubMed

5. Han, M. I.; Kucukguzel, S. G. Anticancer and Antimicrobial Activities of Naproxen and Naproxen Derivatives. Mini Rev. Med. Chem. 2020, 20, 1300–1310; https://doi.org/10.2174/1389557520666200505124922.Search in Google Scholar PubMed

6. Srinivas, S.; Feldman, D. A Phase II Trial of Calcitriol and Naproxen in Recurrent Porstate Cancer. Anticancer Res. 2009, 29, 3605–3610.Search in Google Scholar

7. Kim, M. S.; Kim, J. E.; Lim, D. Y.; Huang, Z.; Chen, H.; Langfald, A.; Lubet, R. A.; Grubbs, C. J.; Dong, Z.; Bode, A. M. Naproxen Induces Cell Cycle Arrest and Apoptosis in Human Urinary Bladder Cancer Cell Lines and Chemically Induced Cancers by Targeting P13–K. Canc. Prev. Res. 2014, 7, 236–245; https://doi.org/10.1158/1940-6207.capr-13-0288.Search in Google Scholar PubMed PubMed Central

8. Liang, D.; Yang, X. H.; Sun, W.; Wang, W. N.; Yang, J. Z.; Liu, Y. Y.; Wang, G. S. Synthesis Crystal Structure and Biological Activities of Naproxen-Eugenol Ester Progrug. Chem. Res. Chinese Univ. 2013, 29, 245–248; https://doi.org/10.1007/s40242-013-2266-9.Search in Google Scholar

9. Wang, L. L.; Xue, D. D. Crystal Structure of 3-phenylpropyl 2-(6-Methoxynaphthalen-2-Yl)propanpate, C23H24O3. Z. Kristallogr. N. Cryst. Struct. 2022, 237, 517–519; https://doi.org/10.1515/ncrs-2022-0114.Search in Google Scholar

10. Wang, L.; Lu, W.; Zhang, J.; Chong, Q.; Meng, F. Cobalt-Catalyzed Regio-Diastereo- and Enantioselective Intermolecular Hydrosilylation of 1,3-Dienes with Prochiral Silanes. Angew. Chem. Int. Ed. 2022, 61, e202205624; https://doi.org/10.1002/anie.202205624.Search in Google Scholar PubMed

Received: 2024-06-14
Accepted: 2024-07-17
Published Online: 2024-08-07
Published in Print: 2024-10-28

© 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. Editorial
  3. Editorial 2024 – New developments and changes of Zeitschrift für Kristallographie – New Crystal Structures
  4. New Crystal Structures
  5. Hydrogen bonding and π⋅⋅⋅halogen interactions in the crystal structure of bis(theophyllinium) hexachloridoplatinate(IV) monohydrate
  6. The crystal structure of 6-amino-2-carboxypyridin-1-ium perchlorate, C6H7ClN2O6
  7. Crystal structure of poly[(μ4-(3-amino-1H-1,2,4-triazol-1-yl)benzene-1,3-dicarboxylato-κ 4 N:O:O':O')(1-methylpyrroldin-2-one-κ1O)dicopper(II)] – 1-methylpyrroldin-2-one (1/3), C40H48Cu2N12O12
  8. The crystal structure of 18-crown-6-k6O6(2,4,5-trinitroimidazol-1-ido-k1O)potassium(I)
  9. Crystal structure of poly[tetraaqua-bis(μ2-5-bromoisophthalato-κ3O,O:O)-(μ2-1,5-bis(imidazol-2-methyl)pentane-κ2N:N)dicadmium(II)] dihydrate
  10. Crystal structure of (5R,6S,E)-5-acetoxy-2-methyl-6-((2aR,3R,5aS,5bS,11aR,12aS)-2a,5a,8,8-tetramethyl-9-oxotetradecahydro-1H,12H-cyclopenta[a]cyclopropa[e]phenanthren-3-yl)hept-2-enoic acid, C32H48O5
  11. The crystal structure of poly[diaqua-bis(μ2 -thiocyanato-κ2N:O)cobalt(II) monohydrate
  12. The crystal structure of 1,3,5-tri(1H-imidazol-1-yl)benzene–2,3,5,6-tetrachlorobenzene-1,4-dicarboxylic acid (1/1)
  13. Crystal structure of dichlorido-bis(1-[(2-ethyl-benzimidazole-1-yl)methyl]-1H–benzotriazole) cadmium(II), C32H32CdN10OCl2
  14. The crystal structure of N′-(tert-butyl)-N′-(3,5-dimethylbenzoyl)-3-methoxy-N,2-dimethylbenzohydrazide, C23H30N2O3
  15. Crystal stucture of 3-benzamido-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluorobenzamide
  16. Crystal structure of bis(μ-benzeneselenolato)-(tetracarbonyl)-{μ-[N-(diphenylphosphanyl)-N-(3-ethynylphenyl)-P,P-diphenylphosphinous amide]} diiron, C48H35Fe2NO4P2Se2
  17. The crystal structure of 2′-(p-tolyl)-4′H-spiro[isochromane-1,1′-naphthalene]-3,4′-dione, C25H18O3
  18. The crystal structure of poly[hexaqua-tetrakis(μ4-pyridine-2,4-dicarboxylate-κ5N: O: O′: O″: O‴)-bi(μ2-pyridine-2,4-dicarboxylate-κ3N: O: O′)-digadolinium(III)tricopper (II)], [Gd2Cu3(C7H3NO4)6(H2O)6] n
  19. Crystal structure of poly[bis(4-(4-(pyridin-4-yl)phenyl)pyridin-1-ium-κ1N)-(μ4-benzene-1,2,4,5-tetracarboxylato-κ5O:O′: O″:O‴:O⁗)-(μ2-2,5-dicarboxyterephthalato-κ2O:O′)dizinc(II)], C52H32N4O16Zn2
  20. The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 2-carboxy-6-nitrobenzoate monohydrate, C24H25FN4O10
  21. Crystal structure of dichlorido-(1-((3,5-dimethyl-2,3-dihydro-1H-1,2,3-triazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-k1N)zinc(II), C22H24ZnN12Cl2
  22. The crystal structure of (3-chlorothiophene-2-carboxylato-κ2O, O′)-(2,2′-dipyridyl-κ2N,N′)lead(II), C20H12Cl2N2O4S2Pb
  23. Synthesis and crystal structure of (Z)-4-((1-(3-fluorophenyl)-1H-1,2,3-triazol-4-yl)methylene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, C19H14FN5O
  24. The crystal structure of the coordination compound catena-poly[(18-crown-6-ether-κ6O6)(4,5-dinitroimidazolato-κ1O)potassium(I)]
  25. Crystal structure of 7-(diethylamino)-3-(trifluoroacetyl)-2H-chromen-2-one, C15H14F3NO3
  26. Crystal structure of dichlorido-1-[(2-ethylimidazole-1-yl)methyl]-1H–benzotriazole κ1N zinc(II), C24H26ZnN10Cl2
  27. Crystal and molecular structure of 5-bromopyridine-2,3-diamine
  28. Crystal structure of catena-poly[bis(μ2-1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine-3-carboxylato-k3-O,O:O)hexaqua-dicobalt tetrahydrate], C26H36N4O20Co2
  29. Crystal structure of thiocyanate-κ1N-bis(μ1-2,6-diformyl-4-methylphenol oxime-κ2N,O)-manganese(III) acetonitrile solvate, C21H21MnN6O6S
  30. The crystal structure of pyrrolidin-1-yl pivalate, C9H13NO4
  31. The crystal structure of 2,2′-(2,2-diphenylethene-1,1-diyl)bis(1,4-dimethoxybenzene), C30H28O4
  32. Crystal structure of bis(benzyltrimethylammonium) tetrathiotungstate(VI), {(C6H5CH2)(CH3)3N}2[WS4]
  33. The crystal structure of ethyl (Z)-2-(ethoxymethylene)-3-oxobutanoate, C9H14O4
  34. The crystal structure of (E)-6-bromo-3,5-dimethyl-2-(1-phenylprop-1-en-2-yl)-3Himidazo[4,5b]pyridine, C17H16BrN3
  35. Crystal structure of (3S,3′S,4R,4′S)-3′-(furan-3-yl)-3-hydroxy-4′-methyl-3,5,6′,7′-tetrahydro-1H,3′H-4,5′-spirobi[isobenzofuran]-1,1′(4′H)-dione-methanol (1/1), C21H22O7
  36. Cocrystal structure of progesterone-isophthalic acid, C25H33O4
  37. The crystal structure of 3-(6-fluoro-1H-indol-3-yl)-1-methylquinoxalin-2(1H)-one, C17H12FN3O
  38. Crystal structure of S-(4-carboxybutyl)- l -cysteine
  39. The cocrystal of 2,2′-(hydrazine-1,1-diyl)bis(1H-imidazole-4,5-dicarbonitrile)– methanol (2/3)
  40. Crystal structure of (1′R,2′S,4′R,6′S)-4,6-dihydroxy-1′,8′,8′-trimethyl-3-(3-methylbutanoyl)-4′,8′,6′,1′,7,2′-hexahydro-1H-4′,6′-methanoxanthene-8-carbaldehyde, C23H30O5
  41. Crystal structure of (3,6-di(2-pyridyl)-4-methylphenyl pyridazine-k 2 N,N′)-bis(1-phenyl-pyrazole-κ 2 C,N) iridium(III) hexafluorophosphate, C39H29F6IrN8P
  42. Crystal structure of 1,5-bis[(E)-1-(2-hydroxyphenyl)ethylidene]thiocarbonohydrazide dimethyl sulfoxide monosolvate, C17H18N4O2S·C2H6OS
  43. Crystal structure of (S)-4-(2-(4-(2-acetyl-5-chlorophenyl)-3-methoxy-6-oxopyridazin-1(6H)-yl)-3-phenylpropanamido)benzoic acid monohydrate, C29H26ClN3O7
  44. The crystal structure of 1,3-bis(2,4-dinitro-1H-imidazol-1-yl)propane
  45. Crystal structure of 4-chlorobenzyl (S)-2-(6-methoxynaphthalen-2-yl)propanoate, C21H19ClO3
  46. Crystal structure of 1-(5-(benzo[d][1,3]dioxol-5-yl)-4-benzyl-1-(4-bromophenyl)-4,5-dihydro-1H-1,2,4-triazol-3-yl)ethan-1-one, C24H20BrN3O3
  47. The crystal structure of (Z)-3′-(2-(1-(3,4-dimethyl-phenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene)hydrazinyl)-2′-hydroxy-[1,1′-biphenyl]-3-carboxylicacid ─ methanol (1/1), C26H26N4O5
  48. Crystal structure of (S)-1-phenylpropan-1-aminium (S)-(1-phenylpropyl)carbamate C19H26N2O2
  49. Synthesis and crystal structure of methyl 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate, C18H16BrN3O2S
  50. The crystal structure of trichlorobis(pyridine-2,6-dithio-κS-carbomethylamido)antimony(III), [SbCl3(C9H11N3S2)2]
  51. Crystal structure of 1,8-dihydroxy-3-{[(triphenylstannyl)oxy]carbonyl} anthracene-9,10-dione, C33H22O6Sn
  52. The crystal structure of (E)-4-(2-(pyridin-4-ylmethylene)hydrazine-1-carbonyl)pyridin-1-ium-2-olate dihydrate, C12H14N4O4
  53. The crystal structure of 6-amino-pyridinium-2-carboxylate, C6H6N2O2
  54. The crystal structure of catena-poly[aqua-nitrato-κ3O,O:O′′-(1,10-phenanthroline-κ2N,N)sodium(I)], C24H18N6O7Na2
  55. Retractions
  56. Retraction of: Crystal structure of bis[diaquaisonicotinatosamarium(III)]-µ-isonicotinato-[diisonicotinatocopper(II)], CuSm2(C6H4NO2)8(H2O)4
  57. Retraction of: Crystal structure of aqua(2,2-bipyridine-k 2 N:N′)(nitrato)-(4-aminobenzoato)cadmium(II) nitrate, [Cd(H2O)(NO3)(C10H8N2)(C7H7NO2)][NO3]
Downloaded on 27.12.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2024-0249/html?srsltid=AfmBOoqIvEERio-8uiMh4v21R30OBCf_kgQv1HsHe0AlwpmD685UCFch
Scroll to top button