Home Physical Sciences The crystal structure of (E)-2-ethoxy-1-methoxy-4-(2-(methylsulfonyl)vinyl)benzene, C12H16O4S
Article Open Access

The crystal structure of (E)-2-ethoxy-1-methoxy-4-(2-(methylsulfonyl)vinyl)benzene, C12H16O4S

  • Yong Li ORCID logo EMAIL logo and Jingjing Wang
Published/Copyright: October 9, 2025
Download Article (PDF)
Become an author with De Gruyter Brill
Submit Manuscript Author Information
Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 240 Issue 6

Abstract

C12H16O4S, monoclinic, P21/c (no. 14), a = 10.7916(4) Å, b = 14.2171(5) Å, c = 8.7371(3) Å, β = 107.0210(10)°, V = 1281.77(8) Å3, Z = 4, Rgt(F) = 0.0333, wRref(F2) = 0.0926, T = 170.00 K.

CCDC no.: 2492795

The molecular structure is shown in the figure. Table 1 contains the crystallographic data. The list of the atoms including atomic coordinates and displacement parameters can be found in the cif-file attached to this article.

Table 1:

Data collection and handling.

Crystal: Plate, colourless
Size: 0.13 × 0.1 × 0.03 mm
Wavelength: Ga Kα radiation (1.34139 Å)
μ: 1.49 mm−1
Diffractometer, scan mode: Bruker D8 Venture, φ and ω-scans
θmax, completeness: 60.6°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 15918, 2936, 0.031
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2613
N(param)refined: 157
Programs: Bruker programs, 1 OLEX2, 2 SHELX 3 , 4 , PLATON 5 , 6

1 Source of materials

Purification of the crude title compound, (E)-2-ethoxy-1-methoxy-4-(2-(methylsulfonyl)vinyl)benzene (6 g), was achieved by washing with petroleum ether. The material was suspended in petroleum ether (200 mL), and the solid was isolated by vacuum filtration. After washing the filter cake with additional petroleum ether (10 mL), the product was dried in vacuo at 40 °C, yielding (E)-1-ethoxy-2-methoxy-4-(2-(methylsulfonyl)vinyl)benzene as a white, crystalline powder. Single crystals of X-ray diffraction quality were obtained from the purified material: a solution of the compound (256 mg, 1.0 mmol) in tetrahydrofuran (20 mL) was prepared at room temperature and filtered into a small vial. The vial was covered with a perforated film, and slow evaporation of the solvent at ambient temperature afforded colorless plates over a period of several days.

2 Experimental details

All hydrogen atoms were placed in geometrically idealized positions and refined using a riding model. Methyl groups were treated as idealized rotating groups. The isotropic displacement parameters (Uiso) of the hydrogen atoms were constrained to 1.2 times the Ueq of their parent atom for the aromatic and methylene groups, and 1.5 times the Ueq for the methyl groups.

3 Comment

Apremilast, marketed under the trade name Otezla, is a first-in-class, orally administered small-molecule inhibitor of phosphodiesterase 4 (PDE4). Its development represents a significant advancement in the treatment of chronic inflammatory diseases. Apremilast is primarily indicated for the treatment of moderate-to-severe plaque psoriasis, active psoriatic arthritis, and oral ulcers associated disease. 7 , 8 As the management of these conditions has historically been dominated by injectable biologic agents, the oral route of administration for apremilast provides a critical therapeutic alternative, offering patients greater convenience and a distinct mechanism of action. 9

The title compound, (E)-2-ethoxy-1-methoxy-4-(2-(methylsulfonyl)vinyl)benzene, is a key intermediate in the convergent synthetic route to apremilast. The core framework of apremilast is assembled via a conjugate addition reaction, wherein the vinyl sulfone moiety of the title compound reacts with a nucleophilic phthalimide precursor. The (E)-geometry of this vinyl group is crucial for achieving high reactivity and diastereoselectivity in this transformation.

As part of our ongoing research interest on the structure-activity relationship about the antimicrobial agent, and understanding of hydrogen bonding schemes of related compounds, 10 , 11 , 12 this study presents the crystal structure of the title compound and provides a determination of its structure.

The asymmetric unit of the title compound, contains one discrete molecule (cf. left part of the figure). The molecular structure of the title compound features a vinyl bridge (C2=C3) that connects the methylsulfonyl group to the substituted phenyl ring. The crystal diffraction data unambiguously establishes the configuration of this moiety. The geometry about the C2=C3 double bond is unequivocally assigned as E. This assignment is principally based on the C2–C3 bond distance of 1.328(2) Å, which is characteristic of a double bond, and the observed torsion angle of S1–C2–C3–C4, which is 178.44(11)°. A value proximal to ±180° indicates an anti-periplanar conformation of the connected S1 and C4 atoms across the vinyl group. This arrangement is likely the thermodynamically more stable isomer, as it minimizes the steric hindrance between the bulky sulfonyl and aryl groups.

A distinctive feature in the molecular conformation of the title compound is the high degree of planarity exhibited by its core structure. This extensive planar region comprises the phenyl ring, methoxy and ethoxy groups, vinyl bridge (C2=C3), and the S atom of the sulfonyl group (C4–C5–C6–C7–C8–C9–O3–C10–C11–O4–C12–C3–C2–S1). The RMS deviation of the plane is 0.0396 Å. Among these atoms, the greatest deviation from the calculated plane is observed for the C10 atom of the methoxy group, with a perpendicular distance of 0.1018 Å from the plane. To our best search, this conjugated planar structure moiety has not been previously reported in crystallographic literature. This spatial arrangement appears to achieve a favorable balance between maximizing electronic conjugation effects and minimizing steric hindrance between substituents.

In detail, the phenyl ring itself is planar. The vinyl group is observed to be nearly coplanar with the aromatic ring. This is quantitatively supported by the torsion angle C2–C3–C4–C9 (174.05(14)°). Additionally, the orientations of the methoxy and ethoxy substituents position their oxygen atoms and the first carbon atoms of their alkyl chains almost in the plane of the phenyl ring (e.g., C10–O3–C7–C6 = 5.3(2)°; C11–O4–C8–C9 = 3.8(2)°).

Smaller planar molecular fragments consisting of the phenyl ring, methoxy and ethoxy groups, and vinyl bridge, (C4–C5–C6–C7–C8–C9–O3–C10–C11–O4–C12–C3–C2), have been previously reported in the literature. 13 , 14 , 15

The crystal structure is stabilized by a network of weak C–H⋯O hydrogen bonding interactions (cf. right part of the figure. Some hydrogen atoms are omitted for clarity). These include: C1–H1C⋯O3I with D⋯A = 3.373(2) Å, where I = 1−x, 1−y, 1−z; C2–H2⋯O1II with D⋯A = 3.3093(18) Å, where II = x, 3/2−y, 1/2+z; C5–H5⋯O1III with D⋯A = 3.3997(18) Å, where III = x, 3/2−y, 1/2+z; and C9–H9⋯O2IV with D⋯A = 3.1999(17) Å, where IV = 1−x, 1−y, −z. Additionally, there is an intramolecular hydrogen bond (medium strong): C3–H3⋯O2, with D⋯A distance of 2.8974(17) Å. These interactions connect the molecules into a two-dimensional network structure along the bc direction.

In addition to hydrogen bonds, the crystal packing is further stabilized by π–π stacking interactions. The phenyl rings of adjacent molecules are related through an inversion center and arranged in a parallel-displaced manner. The distance between ring centroids is 3.905 Å, with a perpendicular distance of 3.499 Å and a slippage distance of 1.733 Å.

The structure also exhibits a weak C–H⋯π interaction between a methyl hydrogen atom (H10A) and the phenyl ring of an adjacent molecule, with an H⋯Cg (centroid) distance of 2.95 Å. This intermolecular interaction occurs along the crystallographic direction (x, 3/2 −y, 1/2+z).

Corresponding author: Yong Li, School of Chemical Engineering, Ningbo Polytechnic University, No. 388, Lushan East Road, Ningbo Economic and Technological Development Zone, Beilun District, Ningbo City, 315806, Zhejiang Province, People’s Republic of China; and Ningbo Key Laboratory of High Performance Petroleum Resin Preparation Engineering and Technology, No. 388, Lushan East Road, Ningbo Economic and Technological Development Zone, Beilun District, Ningbo City, 315806, Zhejiang Province, People’s Republic of China, E-mail:

Acknowledgments

We gratefully acknowledge support by Ningbo Polytechnic University Zhejiang Collaborative Innovation Center, and Ningbo Polytechnic Academician Workstation.

  1. Author contribution: 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. Smart and Saint; Bruker AXS Inc.: Madison, Wisconsin, USA, 2019.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 (2), 339–341; https://doi.org/10.1107/s0021889808042726.Search in Google Scholar

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

4. Sheldrick, G. M. Shelxt – Integrated Space-Group and Crystal-Structure Determination. Acta Crystallogr. A 2015, A71, 3–8; https://doi.org/10.1107/s2053273314026370.Search in Google Scholar PubMed PubMed Central

5. Spek, A. L. Single-Crystal Structure Validation with the Program Platon. J. Appl. Crystallogr. 2003, 36 (1), 7–13; https://doi.org/10.1107/s0021889802022112.Search in Google Scholar

6. Spek, A. L. Structure Validation in Chemical Crystallography. Acta Crystallogr. D 2009, D65, 148–155; https://doi.org/10.1107/s090744490804362x.Search in Google Scholar

7. Papp, K.; Reich, K.; Leonardi, C. L.; Kircik, L.; Chimenti, S.; Langley, R. G. B.; Hu, C.; Stevens, R. M.; Day, R. M.; Gordon, K. B.; Korman, N. J.; Griffiths, C. E. M. Apremilast, an Oral Phosphodiesterase 4 (PDE4) Inhibitor, in Patients with Moderate to Severe Plaque Psoriasis: Results of a Phase III, Randomized, Controlled Trial (Efficacy and Safety Trial Evaluating the Effects of Apremilast in Psoriasis [ESTEEM] 1). J. Am. Acad. Dermatol. 2015, 73 (1), 37–49; https://doi.org/10.1016/j.jaad.2015.03.049.Search in Google Scholar PubMed

8. Schafer, P. Apremilast Mechanism of Action and Application to Psoriasis and Psoriatic Arthritis. Biochem. Pharmacol. 2012, 83 (12), 1583–1590; https://doi.org/10.1016/j.bcp.2012.01.001.Search in Google Scholar PubMed

9. Venkateswaralu, J.; Rajendiran, C.; Reddy, N. R.; Connolly, T. J.; Ruchelman, A. L.; Eckert, J.; Frank, A. J. Processes for the Preparation of (S)-1-(3-Ethoxy-4-methoxyphenyl)-2-methanesulfonylethylamine. United States Patent 20130217918A1 2013.Search in Google Scholar

10. Li, Y.; Wang, J. The Crystal Structure of Ethyl 6-(2-nitrophenyl)imidazo[2,1-b]Thiazole-3-Carboxylate, C14H11N3O4S. Z. Kristallogr. N. Cryst. Struct. 2025, 240 (3), 479–481; https://doi.org/10.1515/ncrs-2025-0069.Search in Google Scholar

11. Li, Y.; Wu, Y.; Wang, J. The Crystal Structure of 3-((4-Chloro-N-(2-methoxyethyl)benzamido)methyl)phenyl Methanesulfonate, C18H20ClNO5S. Z. Kristallogr. N. Cryst. Struct. 2022, 237 (6), 1033–1036; https://doi.org/10.1515/ncrs-2022-0376.Search in Google Scholar

12. Wang, J.; Wu, Y.; Li, Y. The Crystal Structure of Ethyl 2,3,5-trifluoro-4-(4-oxo-3,4-dihydropyridin-1(2H)-yl)benzoate, C14H12F3NO3. Z. Kristallogr. N. Cryst. Struct 2022, 237 (6), 1087–1089; https://doi.org/10.1515/ncrs-2022-0412.Search in Google Scholar

13. Huck, D. M.; Nguyen, H. L.; Horton, P. N.; Hursthouse, M. B.; Guillon, D.; Donnio, B.; Bruce, D. W. Mesomorphic Silver(I) Complexes of Polycatenar 2′- and 3′-Stilbazoles. Crystal and Molecular Structure of 3,4-Dimethoxy-3′-Stilbazole and of Two Silver Triflate Complexes. Polyhedron 2006, 25 (2), 307–324; https://doi.org/10.1016/j.poly.2005.07.023.Search in Google Scholar

14. Kolev, T.; Yancheva, D.; Kleb, D.-C.; Schürmann, M.; Glavcheva, Z.; Preut, H.; Bleckmann, P. Crystal Structure of 2-{3-[2-(3-Ethoxy-4-methoxy-phenyl)-viny 1]-5,5-dimethyl-cyclohex-2-enylidene}-malononitrile, C22H24N2O2. Z. Kristallogr. N. Cryst. Struct. 2001, 216 (1–4), 67–68; https://doi.org/10.1524/ncrs.2001.216.14.67.Search in Google Scholar

15. Jasinski, J. P.; Miller, W. M.; Samshuddin, S.; Narayana, B.; Yathirajan, H. S. (2E)-3-{4-[(1H-1,3-Benzimidazol-2-yl)methoxy]-3-ethoxyphenyl}-1-(4-bromophenyl)prop-2-en-1-one Monohydrate. Acta Crystallogr. E 2011, 67 (4), o834–o835; https://doi.org/10.1107/s1600536811008154.Search in Google Scholar
Received: 2025-08-15
Accepted: 2025-10-02
Published Online: 2025-10-09
Published in Print: 2025-12-17

© 2025 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. The crystal structure of (1Z, 2Z)-3-phenyl-2-propenal 2-(4-bromo-2-fluorophenyl)hydrazone, C15H12BrFN2
  4. Refinement of crystal structure of 2-(2,3-dihydro-3-oxo-1 H -inden-1-ylidene)-1 H -indene-1,3(2 H )-dione C18H10O3
  5. The crystal structure of 3-(1-fluoro-2-(naphthalen-2-yl)-2-oxoethyl)-2-methoxy-3,4-dihydroisoquinolin-1(2H)-one, C22H18FNO3
  6. Crystal structure of the dinuclear copper(II) complex bis(μ2-2,2′ -{[1,3-phenylenebis-(methylene)]bis(oxy)}dibenzoaot-κ4O,O′:O′′,O′′′)-bis(dimethylformamide-κ1O)dicopper(II), C50H44Cu2N2O14
  7. Crystal structure of poly[triaqua-(μ9-biphenyl-3,3′,5,5′-tetracarboxylic-κ8 O,O:O,O′: O,O″:O,O‴)samarium(III)sodium(I)], C16H12NaSmO11
  8. The crystal structure of 5-benzyl-1-(4-fluorobenzyl)-4-((4-fluorobenzyl)oxy)-1,5-dihydro-2H-pyrrol-2-one, C25H21F2NO2
  9. The crystal structure of diammonium 2,5-dihydroxyterephthalate, C8H12N2O6
  10. Crystal structure of (E)-4-(4-(1H-1,2,4-triazol-1-yl)benzylidene)-6,8-dimethoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, C21H19N3O4
  11. Crystal structure of poly[oktakis(μ2-oxido-κ2O:O)-tetrakis(oxido-κ1O)-bis(μ2-1,1′-[1,4-phenylenebis(methylene)]di(1H-imidazole-κ2N:N′))-tetravanadium(V)-dizinc(II)] monohydrate, C28H30Zn2N8O13V4
  12. Crystal structure of acotiamide hydrochloride dimethylacetamide solvate (1/1), C25H40ClN5O6S
  13. Crystal structure of catena-poly[monoaqua (u2-(3-(3,5-dicarboxyphenyl)pyridine-2,6-dicarboxylic-k4O:O′:O″:N)zinc(II))] monohydrate, C15H11NO10Zn
  14. Crystal structure of dichlorido{2,6-bis(3,5-diisopropyl-N-pyrazolyl)pyridine}zinc(II), C23H33Cl2N5Zn
  15. Crystal structure of nitrato-κ2O,O′-[hydridotris(3,5-diethylpyrazol-1-yl)borato-κ3N,N′,N″]copper(II), C21H34BCuN7O3
  16. Crystal structure of 2,7-bis(3,5-diethyl-1H-pyrazol-4-yl)-benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone, C28H26N6O4
  17. Crystal structure of 2-(4-chlorophenyl)benzothiazole, C13H8ClNS
  18. Synthesis and crystal structure (3R,4′S)-4′-(3,5-dibromophenyl)-1′-methyl-2H-dispiro [benzofuran-3,3′-pyrrolidine-2′,2″-indene]-1″,2,3″-trione, C26H17Br2NO4
  19. Crystal structure of bis(((3a,7a-dihydro-1H-benzo[d][1,2,3]triazol-1-yl)methyl) triphenylphosphonium) tetrachloridomanganate(II), C50H42Cl4MnN6P2
  20. The crystal structure of 4,9-bis(4-chlorophenyl)-1,6-bis(2-cyanobenzyl)-2,4a,5,6,7,7a-hexahydro-1H-2,7,5-(epiprop[2]ene[1,1,3]triyl)pyrrolo[3,4-b]pyridine-3,10-dicarbonitrile, C40H26Cl2N6
  21. The crystal structure of poly((μ2-3-(3-nitro-4-carboxylphenyl)benzoate-κ3O, O′:O″)-μ2-1,4-bis(1-imidazolyl)benzene-κ2N:N′-cadmium(II)), C26H17N5O6Cd
  22. The crystal structure of 6-hydroxy-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione monohydrate, C7H6N2O4
  23. Crystal structure of 4-((cyclohexylsulfonyl)methyl)-1,2,3,4-tetrahydrobenzo [4,5]imidazo[1,2-a]pyridine, C18H24N2O2S
  24. Crystal structure of 4,7-diphenyl-1,10-phenanthroline-κ2N,N′)-bis(2,4-di(fluorine)-1-phenylpyridine-κ2C,N)-iridium(III) hexafluorophosphate–dichloromethane (1/1), C47H30Cl2F10IrN4P
  25. Crystal structure of (4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)boronic acid, C19H15BN2O2
  26. The crystal structure of (E)-(2-((pyridin-2-ylmethylene)amino)phenyl)arsonic acid, C12H11AsN2O3
  27. The crystal structure of N(benzyl(phenyl)carbomothioyl)benzamide, C21H18N2OS
  28. The crystal structure of bis(2-picolinium) hexachlorostannate dichloromethane monosolvate, C13H18Cl8N2Sn
  29. Crystal structure of poly[tetraaqua-bis(μ4-3–1-(carboxylatomethyl)-1H-1,2,4-triazole-3-carboxylato)-κ4O:O′,O″,N)zinc(II)], C5H7N3O6Zn
  30. The crystal structure of the co-crystal isonicotinamide – 2-(nitrophenyl)methanol (1/1), C6H6N2O·C7H7NO3
  31. The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 2-fluorobenzoate hydrate, C23H25F2N3O6
  32. Crystal structure of [diaqua-{1H-benzo[d]imidazol-3-ium-5,6-dicarboxylato-κ2O,O′}magnesium(II)] C18H14MgN4O10
  33. Crystal structure of (3-(dimethoxymethyl)-5-methoxy-1H-indol-1-yl) (2-iodo-5-methoxyphenyl)methanone, C20H20INO5
  34. The crystal structure of 3,7,11-trimethylbenzo[5,6][1,4]thiazino[2,3,4-kl]phenothiazine 5,5,9,9-tetraoxide, C21H17NO4S2
  35. Crystal structure of tris(piperazine-1,4-diium)bis(2-hydroxy-1,2,3-propane-tricarboxylate) pentahydrate, C24H56N6O19
  36. Crystal structure of 2-chloro-5-((5-isopropyl-2-methylphenoxy)methyl)pyridine, C16H18ClNO
  37. Crystal structure of (E)-4-(4-(1H-pyrrol-1-yl)benzylidene)-6,8-dimethoxy-3,4-dihydrobenzo[(b)]oxepin-5(2H)-one, C23H21NO4
  38. Crystal structure of (E)-N′-(3,4-dichlorobenzylidene)-3,4,5-trimethoxybenzohydrazide, C17H16Cl2N2O4
  39. The crystal structure of 2-(2-hydroxyphenyl)-3-(pyridin-2-yl)-2,3- dihydroquinazolin-4(1H)-one, C19H15N3O2
  40. Crystal structure of 5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-8-methylchroman-4-one, C17H16O5
  41. Crystal structure of bis[(3,4-dimethoxybenzyl)triphenylphosphonium]di-μ2-bromido-dibromidodicopper(I)
  42. Crystal structure of bis [(1,3-dioxolan-2-ylmethyl)triphenylphosphonium] tetrabromidodicopper(I), C22H22Br2CuO2P
  43. Crystal structure of [1-(4-carboxyphenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylic acid], C12H8N2O5
  44. The crystal structure of one-dimensional cooridnation polymer bis(thiocyanato)-bis((1E,2E)-1,2-bis(1-(pyridin-3-yl)ethylidene)-hydrazine κ2N:N)iron(II), (C30H28N10S2Fe)n
  45. Crystal structure of ((4-acetamidophenyl)sulfonyl)-l-alanine, C11H14N2O5S
  46. Crystal structure of [(1-naphthalen-1-yl-methyl)triphenylphosphonium] dichloridocopper(I), [C29H24P]+[CuCl2]−
  47. RbTm3S5: the first rubidium lanthanoid(III) sulfide with CsEr3Se5-type crystal structure
  48. Crystal structure of 2,2′-((ethane-1,2-diylbis(methylammoniumdiyl))bis(methylene))bis(pyridin-1-ium) diiodido-tris(μ2-iodido-κ2I:I)dicopper(II) chloride dihydrate, C16H30Cu2I6N4O2
  49. The crystal structure of 4-(trifluoromethyl)pyridine-2-carboxylic acid, C7H4F3NO2
  50. The crystal structure of (E)-2-ethoxy-1-methoxy-4-(2-(methylsulfonyl)vinyl)benzene, C12H16O4S
  51. Crystal structure of potassium 1H,1H,2H,2H-perfluorooctanesulfonate, C8H4O3F13SK
  52. Crystal structure of 4-(4-(quinolin-8-yloxy)-1,2,5-thiadiazol-3-yl)morpholine, C15H14O2N4S
  53. The crystal structure of 1,4-bis(bromomethyl)-2,5-dimethylbenzene, C10H12Br2
  54. The crystal structure of imidazo[4,5-e][1,3]diazepine-4,6,8-triamine methanol solvate, C7H11N7O
  55. The crystal structure of chlorido-bis(1,10-phenantroline-κ2N,N′)-(2-formylphenoxyacetato-κ2O,O) lead(II), C33H23N4O4ClPb
  56. Crystal structure of pyridinium tetrakis(1,1,1-trifluoro-2,4-pentadionato-κ2O,O′)yttrium(III) C20F12H16YO8C5H6N
https://doi.org/10.1515/ncrs-2025-0360
Creative Commons
BY 4.0

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of (1Z, 2Z)-3-phenyl-2-propenal 2-(4-bromo-2-fluorophenyl)hydrazone, C15H12BrFN2
  4. Refinement of crystal structure of 2-(2,3-dihydro-3-oxo-1 H -inden-1-ylidene)-1 H -indene-1,3(2 H )-dione C18H10O3
  5. The crystal structure of 3-(1-fluoro-2-(naphthalen-2-yl)-2-oxoethyl)-2-methoxy-3,4-dihydroisoquinolin-1(2H)-one, C22H18FNO3
  6. Crystal structure of the dinuclear copper(II) complex bis(μ2-2,2′ -{[1,3-phenylenebis-(methylene)]bis(oxy)}dibenzoaot-κ4O,O′:O′′,O′′′)-bis(dimethylformamide-κ1O)dicopper(II), C50H44Cu2N2O14
  7. Crystal structure of poly[triaqua-(μ9-biphenyl-3,3′,5,5′-tetracarboxylic-κ8 O,O:O,O′: O,O″:O,O‴)samarium(III)sodium(I)], C16H12NaSmO11
  8. The crystal structure of 5-benzyl-1-(4-fluorobenzyl)-4-((4-fluorobenzyl)oxy)-1,5-dihydro-2H-pyrrol-2-one, C25H21F2NO2
  9. The crystal structure of diammonium 2,5-dihydroxyterephthalate, C8H12N2O6
  10. Crystal structure of (E)-4-(4-(1H-1,2,4-triazol-1-yl)benzylidene)-6,8-dimethoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, C21H19N3O4
  11. Crystal structure of poly[oktakis(μ2-oxido-κ2O:O)-tetrakis(oxido-κ1O)-bis(μ2-1,1′-[1,4-phenylenebis(methylene)]di(1H-imidazole-κ2N:N′))-tetravanadium(V)-dizinc(II)] monohydrate, C28H30Zn2N8O13V4
  12. Crystal structure of acotiamide hydrochloride dimethylacetamide solvate (1/1), C25H40ClN5O6S
  13. Crystal structure of catena-poly[monoaqua (u2-(3-(3,5-dicarboxyphenyl)pyridine-2,6-dicarboxylic-k4O:O′:O″:N)zinc(II))] monohydrate, C15H11NO10Zn
  14. Crystal structure of dichlorido{2,6-bis(3,5-diisopropyl-N-pyrazolyl)pyridine}zinc(II), C23H33Cl2N5Zn
  15. Crystal structure of nitrato-κ2O,O′-[hydridotris(3,5-diethylpyrazol-1-yl)borato-κ3N,N′,N″]copper(II), C21H34BCuN7O3
  16. Crystal structure of 2,7-bis(3,5-diethyl-1H-pyrazol-4-yl)-benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone, C28H26N6O4
  17. Crystal structure of 2-(4-chlorophenyl)benzothiazole, C13H8ClNS
  18. Synthesis and crystal structure (3R,4′S)-4′-(3,5-dibromophenyl)-1′-methyl-2H-dispiro [benzofuran-3,3′-pyrrolidine-2′,2″-indene]-1″,2,3″-trione, C26H17Br2NO4
  19. Crystal structure of bis(((3a,7a-dihydro-1H-benzo[d][1,2,3]triazol-1-yl)methyl) triphenylphosphonium) tetrachloridomanganate(II), C50H42Cl4MnN6P2
  20. The crystal structure of 4,9-bis(4-chlorophenyl)-1,6-bis(2-cyanobenzyl)-2,4a,5,6,7,7a-hexahydro-1H-2,7,5-(epiprop[2]ene[1,1,3]triyl)pyrrolo[3,4-b]pyridine-3,10-dicarbonitrile, C40H26Cl2N6
  21. The crystal structure of poly((μ2-3-(3-nitro-4-carboxylphenyl)benzoate-κ3O, O′:O″)-μ2-1,4-bis(1-imidazolyl)benzene-κ2N:N′-cadmium(II)), C26H17N5O6Cd
  22. The crystal structure of 6-hydroxy-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione monohydrate, C7H6N2O4
  23. Crystal structure of 4-((cyclohexylsulfonyl)methyl)-1,2,3,4-tetrahydrobenzo [4,5]imidazo[1,2-a]pyridine, C18H24N2O2S
  24. Crystal structure of 4,7-diphenyl-1,10-phenanthroline-κ2N,N′)-bis(2,4-di(fluorine)-1-phenylpyridine-κ2C,N)-iridium(III) hexafluorophosphate–dichloromethane (1/1), C47H30Cl2F10IrN4P
  25. Crystal structure of (4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)boronic acid, C19H15BN2O2
  26. The crystal structure of (E)-(2-((pyridin-2-ylmethylene)amino)phenyl)arsonic acid, C12H11AsN2O3
  27. The crystal structure of N(benzyl(phenyl)carbomothioyl)benzamide, C21H18N2OS
  28. The crystal structure of bis(2-picolinium) hexachlorostannate dichloromethane monosolvate, C13H18Cl8N2Sn
  29. Crystal structure of poly[tetraaqua-bis(μ4-3–1-(carboxylatomethyl)-1H-1,2,4-triazole-3-carboxylato)-κ4O:O′,O″,N)zinc(II)], C5H7N3O6Zn
  30. The crystal structure of the co-crystal isonicotinamide – 2-(nitrophenyl)methanol (1/1), C6H6N2O·C7H7NO3
  31. The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 2-fluorobenzoate hydrate, C23H25F2N3O6
  32. Crystal structure of [diaqua-{1H-benzo[d]imidazol-3-ium-5,6-dicarboxylato-κ2O,O′}magnesium(II)] C18H14MgN4O10
  33. Crystal structure of (3-(dimethoxymethyl)-5-methoxy-1H-indol-1-yl) (2-iodo-5-methoxyphenyl)methanone, C20H20INO5
  34. The crystal structure of 3,7,11-trimethylbenzo[5,6][1,4]thiazino[2,3,4-kl]phenothiazine 5,5,9,9-tetraoxide, C21H17NO4S2
  35. Crystal structure of tris(piperazine-1,4-diium)bis(2-hydroxy-1,2,3-propane-tricarboxylate) pentahydrate, C24H56N6O19
  36. Crystal structure of 2-chloro-5-((5-isopropyl-2-methylphenoxy)methyl)pyridine, C16H18ClNO
  37. Crystal structure of (E)-4-(4-(1H-pyrrol-1-yl)benzylidene)-6,8-dimethoxy-3,4-dihydrobenzo[(b)]oxepin-5(2H)-one, C23H21NO4
  38. Crystal structure of (E)-N′-(3,4-dichlorobenzylidene)-3,4,5-trimethoxybenzohydrazide, C17H16Cl2N2O4
  39. The crystal structure of 2-(2-hydroxyphenyl)-3-(pyridin-2-yl)-2,3- dihydroquinazolin-4(1H)-one, C19H15N3O2
  40. Crystal structure of 5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-8-methylchroman-4-one, C17H16O5
  41. Crystal structure of bis[(3,4-dimethoxybenzyl)triphenylphosphonium]di-μ2-bromido-dibromidodicopper(I)
  42. Crystal structure of bis [(1,3-dioxolan-2-ylmethyl)triphenylphosphonium] tetrabromidodicopper(I), C22H22Br2CuO2P
  43. Crystal structure of [1-(4-carboxyphenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylic acid], C12H8N2O5
  44. The crystal structure of one-dimensional cooridnation polymer bis(thiocyanato)-bis((1E,2E)-1,2-bis(1-(pyridin-3-yl)ethylidene)-hydrazine κ2N:N)iron(II), (C30H28N10S2Fe)n
  45. Crystal structure of ((4-acetamidophenyl)sulfonyl)-l-alanine, C11H14N2O5S
  46. Crystal structure of [(1-naphthalen-1-yl-methyl)triphenylphosphonium] dichloridocopper(I), [C29H24P]+[CuCl2]−
  47. RbTm3S5: the first rubidium lanthanoid(III) sulfide with CsEr3Se5-type crystal structure
  48. Crystal structure of 2,2′-((ethane-1,2-diylbis(methylammoniumdiyl))bis(methylene))bis(pyridin-1-ium) diiodido-tris(μ2-iodido-κ2I:I)dicopper(II) chloride dihydrate, C16H30Cu2I6N4O2
  49. The crystal structure of 4-(trifluoromethyl)pyridine-2-carboxylic acid, C7H4F3NO2
  50. The crystal structure of (E)-2-ethoxy-1-methoxy-4-(2-(methylsulfonyl)vinyl)benzene, C12H16O4S
  51. Crystal structure of potassium 1H,1H,2H,2H-perfluorooctanesulfonate, C8H4O3F13SK
  52. Crystal structure of 4-(4-(quinolin-8-yloxy)-1,2,5-thiadiazol-3-yl)morpholine, C15H14O2N4S
  53. The crystal structure of 1,4-bis(bromomethyl)-2,5-dimethylbenzene, C10H12Br2
  54. The crystal structure of imidazo[4,5-e][1,3]diazepine-4,6,8-triamine methanol solvate, C7H11N7O
  55. The crystal structure of chlorido-bis(1,10-phenantroline-κ2N,N′)-(2-formylphenoxyacetato-κ2O,O) lead(II), C33H23N4O4ClPb
  56. Crystal structure of pyridinium tetrakis(1,1,1-trifluoro-2,4-pentadionato-κ2O,O′)yttrium(III) C20F12H16YO8C5H6N
Sign up now to receive a 20% welcome discount
Institutional Access
How does access work?
Have an idea on how to improve our website?
Please write us.
© 2025 De Gruyter Brill
Downloaded on 8.12.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2025-0360/html
Scroll to top button