Home Crystal structure of N-isopropyl-1,8-naphthalimide C15H13NO2
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Crystal structure of N-isopropyl-1,8-naphthalimide C15H13NO2

  • Weifeng He , Yingfan Liu EMAIL logo and Jingjing Bi
Published/Copyright: April 3, 2025
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 240 Issue 3

Abstract

C15H13NO2, orthorhombic, Cmce (no. 64), a = 7.0048(4) Å, b = 18.0939(7) Å, c = 19.2281(8) Å, V = 2437.0 Å3, Z = 8, R gt (F) = 0.0614, wR ref (F2) = 0.1989, T = 293.9(10) K.

CCDC no.: 2423748

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

Figure: A view of the molecule. Displacement ellipsoids are drawn at the 50 % probability level and H atoms are shown as small spheres of arbitrary radii.
Figure:

A view of the molecule. Displacement ellipsoids are drawn at the 50 % probability level and H atoms are shown as small spheres of arbitrary radii.

Table 1:

Data collection and handling.

Crystal: Yellow block
Size: 0.24 × 0.18 × 0.15 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 0.70 mm−1
Diffractometer, scan mode: Rigaku, ω scans
θmax, completeness: 66.6°, 98 %
N(hkl)measured, N(hkl)unique, Rint: 3063, 1164, 0.016
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 917
N(param)refined: 107
Programs: Rigaku 1 , SHELX 2 , 3 , 4 , Olex2 5

1 Source of material

The title compound was synthesized according to the literature reported condensation methodology with slight modification. 6 According to the literature procedure, acetic acid and benzene were used as reaction solvent and eluent in column chromatography, respectively. The operating procedure is tedious and harmful to the environment. Therefore, we update the synthetic procedure with anhydrous ethanol, which is more removable than acetic acid. 1,8-naphthalic anhydride (1.98 g, 10 mmol) was mixed with 300 mL anhydrous ethanol. The mixture was heated to reflux for about 30 min. Then, isopropylamine (2 mL) was dissolved in 10 mL anhydrous ethanol and added dropwisely to the above reaction mixture. Subsequently, it was refluxed for another 2 h. The reaction progress was monitored by thin – layer chromatography (TLC). When the starting 1,8-naphthalic anhydride disappeared completely on the TLC, the refluxing apparatus was changed to distilling apparatus, removing 220 mL ethanol. The left mixture was cooled to 0 °C and stand still to precipitate crystalline. The precipitate was collected and washed throughly with ethanol. Analytical sample was obtained by double recrystallization in ethanol. The purified N-isopropyl-1,8-naphthalimide (100 mg) was dissolved in 10 mL ethanol in a 20 mL vial with parafilm covered. Three to five holes were made with the needle on the parafilm cover. After several days slow evaporation of the ethanol solution at room temperature, crystals generated at the bottom of the vial. Suitable crystal was selected for X-ray diffraction and data was collected.

2 Experimental details

The structure of N-isopropyl-1,8-naphthalimide was solved using ShelXt and refined by ShelXl through the Olex2 interface. 2 , 3 Hydrogen atoms attached to C atoms were placed geometrically and refined using a riding model approximation, with d(C–H) = 0.93 Å, 0.96 Å, or 0.98 Å (–CH, –CH3, –CH2). Uiso(H) = 1.2Ueq(C) for CH or Uiso(H) = 1.5Ueq(C) for CH3 and CH2 groups. 2 C2/C3/C4/C8/C9/C10 were restricted by RIGU command to the reasonable thermal ellipsoids. According to the data refinement, the resolution was set to be 0.84 Å. The molecular graphics were drawn using the software DIAMOND with 50 % probability ellipsoids in the figure. 7

3 Comment

The N-isopropyl-1,8-naphthalimide is a classical fluorescent dye with build-in naphthalimide framework, which has strong green fluorescence emission both in solution and in solid state when irradiated with 365 nm UV light. Therefore, various naphthalimide-containing fluorescent dyes were developed to be applied in chemsensor configuration, cell imaging, dye-sensitized solar cells device fabrication, etc. 8 , 9 , 10 , 11 , 12 Generally, the bromine atom is easy to be introduced to the four-position of naphthalic anhydride, generating 4-bromo-1,8-naphthalic anhydride. And the active bromine atom can be substituted by N/O based electron donating group, establishing the intramolecular electron push-pull effect with the electron withdrawing imide moiety. Together with the π system of naphthalene, the emission of naphthalimide-containing dye could be modified according to the requirement of material and/or optical devices. In case of N -isopropyl-1,8-naphthalimide, those having 4-substituent naphthalimide derivatives can be configured as various longer wavelength emission dyes. 13 , 14 , 15 Chemsensors that can responsive to anions, cations, and/or small biological molecules were developed.

In the title crystal structure, the asymmetric unit contains half molecules. Both the bond lengths and the angles are in the expected ranges. Except for C14, the whole molecular framework is coplanar. The isopropyl was split into symmetrical geometry configuration and therefore C14 was distributed to both sides of the naphthalimide plane of symmetry. The bond lengths C11–O1 and C12–O2 are determined to be 1.212 and 1.218 Å, respectively, having the typical character of double bond. The C11/C12 of carbonly group is sp2 hybridized. In addition, the bond length of C11–N1/C12–N1 (1.377 and 1.398 Å) is shorter than that of C13–N1 (1.494 Å) and has partial character of double bond. It indicates that the two carbonyl groups (C11–O1 and C12–O2) configured the imide group, having strong power of electron-withdrawing. Totally, the π system of naphthalene and the electron acceptor (imide group) jointly configured the intramolecular electron “push-pull” effect in a fluorescent dye molecular system. Once more stronger electron donating unit was introduced furtherly, various modificable fluorescent naphthalimide-containing dyes can be widely developed. 16 , 17 , 18 , 19 The adjacent parallel molecules are jointed by strong π⋯π interaction. The distance between the naphthalimide plane (C1/C2/C4/C5/C6/C7/C8/C9/C10//C11/C12/N1i1, i1:x, y, z) and the parallel one (C1/C2/C4/C5/C6/C7/C8/C9/C10//C11/C12/N1i2 i2:1/2−x, +y, 3/2−z) is determined to be 3.502 Å and the parallel shift is 1.205 Å, corresponding to the parallel-displaced geometry. 20 Additionally, typical intramolecular C–H⋯O interactions are established. The configuration of isopropyl was locked by the C14–H14A⋯O1i1, which makes the plane of C14/C13/C14i3 (i3: 1−x, +y, +z) perpendicular to the plane of the naphthalimide plane (C1/C2/C4/C5/C6/C7/C8/C9/C10//C11/C12/N1i1). The distance of C14⋯O1 and H14A⋯O1 is estimated to be 2.975 and 2.430 Å with the C–H⋯O angle being 115.7°. Of course, another carbonyl O2 also involved in the intermolecular hydrogen bond construction. The H⋯O contact is C114i4–H14C⋯O2 (i4: 1/2+x, 1/2−y, 1−z) with the H⋯O distance being 2.706 Å. Both the inter- and intra-molecular C–H⋯O angles are in agreement with the above mentioned survey. 21 , 22 The construction of weak hydrogen bonds in the crystal is significant to understand the emission properties of the fluorescent dyes in solid state. 23 , 24 , 25 , 26 , 27 Therefore, reasonable introduction of different inter- and/or intra-molecular hydrogen bonds into the crystal lattice is key to modify the ratio between the radiative and nonradiative channels. 28 , 29 Once the stronger intramolecular interactions are established between dye molecules, more nonradiative channels will be established for the excited molecules and thus quenching the fluorescent emission. 30 , 31 , 32 , 33

In the crystal, the dye molecules are regularly packed by the intermolecular force, including hydrogen bonds and π⋯π interactions. The driving force for the title molecule packing parallel to each other along the axis a is based on the π⋯π interaction. While, the parallel molecules are joined by the hydrogen bonds. 34 , 35 The weaker interactions distributed in the titly packed dye molecules turn on/off the highly emissive character in crystal/solid state. 34 , 35 , 36 With the establishing of the T-shaped π⋯π interaction, the naphthimide part promotes the tightly packed model. However, the perpendicular isopropyl inhibited this packing trend in some degree. The comprehensive result leads to an appropriate emission channel and highly green emission character of naphthalimide. 37 , 38 , 39 , 40 , 41 The nonradiative channel of excited dye molecules is easy to be interfered by the external environment. Therefore, it is very important to intra- and inter-molecular interactions, establishing a higher proportion emission channel. 42 , 43 To the title N-isopropyl-1,8-naphthalimide, the unique packing model, together with its intramolecular electron “push-pull” system, does establish its recognizable optical property and biological application. 44 , 45 It also shows that the reasonable introduction of heteroatom-containing moiety and/or aromatic ring system is an effective way in fluorescent dye designing. 46 , 47 , 48 In conclusion, the title molecules are staggered layer by layer along with axis b and c by the strong π⋯π interaction. While, the hydrogen bonds based on H⋯O contacts joint the parallel adjacent molecules.

Corresponding author: Yingfan Liu, College of Material and Chemical Engineering, Zhengzhou University of Light Industry, Henan Provincial Key Lab of Surface and Interface Science, Zhengzhou, 450002, P.R. China, E-mail:

Acknowledgments

The authors gratefully thank Prof. Xiaochuan Li (Henan Normal University) for his assistance with the lab facilities supportation/chemical purification, single crystal X-ray diffraction data acquisition and providing his expertise on crystal diffraction data solving.

References

1. Oxford Diffraction Ltd. CrysAlisPRO: Abingdon, Oxfordshire, England, 2006.Search in Google Scholar

2. Sheldrick, G. M. Crystal Structure Refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8.10.1107/S2053229614024218Search in Google Scholar PubMed PubMed Central

3. Sheldrick, G. M. A Short History of SHELX. Acta Crystallogr. 2008, A64, 112–122. https://doi.org/10.1107/s0108767307043930.Search in Google Scholar PubMed

4. Sheldrick, G. M. SHELXTL–Integrated Space-Group and Crystal-Structure Determination. Acta Crystallogr. 2015, A71, 3–8.10.1107/S2053273314026370Search in Google Scholar PubMed PubMed Central

5. 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

6. Prezhdo, O. V.; Upenskii, B. V.; Prezhdo, V. V.; Boszczyk, W.; Distanov, V. B. Synthesis and Spectral-Luminescent Characteristics of N-Substituted 1,8-Naphthalimides. Dyes Pigm. 2007, 72, 42–46. https://doi.org/10.1016/j.dyepig.2005.07.022.Search in Google Scholar

7. Brandenburg, K. DIAMOND. Visual Crystal Structure Information System. Version 4.6; Crystal Impact: Bonn, Germany, 1997–2022.Search in Google Scholar

8. Zheng, X.; Liu, X.; Liu, L.; Li, X.; Jiang, S.; Niu, C.; Xie, P.; Liu, G.; Cao, Z.; Ren, Y.; Qin, Y.; Wang, J. Multi-Stimuli-Induced Mechanical Bending and Reversible Fluorescence Switching in a Single Organic Crystal. Angew. Chem., Int. Ed. 2022, 61, e202113073. https://doi.org/10.1002/anie.202113073.Search in Google Scholar PubMed

9. Li, X.; Han, Y.; Sun, S.; Shan, D.; Ma, X.; He, G.; Mergu, N.; Park, J.-S.; Kim, C.-H.; Son, Y.-A. A Diaminomaleonitrile-Appended BODIPY Chemosensor for the Selective Detection of Cu2+ via Oxidative Cyclization and Imaging in SiHa Cells and Zebrafish. Spectrochim. Acta, Part A 2020, 233, 118179. https://doi.org/10.1016/j.saa.2020.118179.Search in Google Scholar PubMed

10. Li, J.; Xu, B. S.; hang, X.; Zhao, L. L.; Yi, S. Z.; Li, B. N. Recent Advances in Smart Sensing Based on Excited-State Intramolecular Proton-Transfer (ESIPT)-Inspired Emitters. Asian J. Org. Chem. 2025, 14, e202400572. https://doi.org/10.1002/ajoc.202400572.Search in Google Scholar

11. Li, X.; Liu, X.; Li, F. Configuration of Super-Fast Cu2+-Responsive Chemosensor by Attaching Diaminomaleonitrile to BODIPY Scaffold for High-Contrast Fluorescence Imaging of Living Cells. Spectrochim. Acta, Part A 2024, 304, 123377. https://doi.org/10.1016/j.saa.2023.123377.Search in Google Scholar PubMed

12. Xie, P.; Zhou, Y.; Li, X.; Liu, X.; Liu, L.; Cao, Z.; Wang, J.; Zheng, X. Strong Dual-State Emission of Unsymmetrical and Symmetrical Thiazolothiazole-Bridged Imidazolium Salts. Chin. Chem. Lett. 2023, 34, 107582. https://doi.org/10.1016/j.cclet.2022.06.005.Search in Google Scholar

13. Li, X.; Han, Y.; Kim, M.; Son, Y. A. A BODIPY-Based Highly Emissive Dye with Thiophene-Based Branch Harvesting the Light. Mol. Cryst. Liq. Cryst. 2018, 662, 157–164. https://doi.org/10.1080/15421406.2018.1467613.Search in Google Scholar

14. Liu, Y.; Li, X.; Min, K. S.; Son, Y. A. Highly Fluorescent Response of 4-(2,5-Dimethylthiophen-3-yl)-2-hydroxyphenylbenzothiazole Toward BF3∙Et2O and Zn2+. Mol. Cryst. Liq. Cryst. 2018, 662, 132–138; https://doi.org/10.1080/15421406.2018.1466531.Search in Google Scholar

15. Li, X.; Han, Y.; Min, K.; Son, Y. A. Configuration of White Light Emission by Courmarin and Naphthalimide. Mol. Cryst. Liq. Cryst. 2018, 660, 10–16. https://doi.org/10.1080/15421406.2018.1452861.Search in Google Scholar

16. Li, X.; Li, F.; Ji, G. A Fluorescent Turn-On Sensor Toward Multiple Heavy Metal Ions Based on Meso-Anisole Modified BODIPY Scaffold. J. Fluoresc. 2023, 33, 631–637; https://doi.org/10.1007/s10895-022-03110-1.Search in Google Scholar PubMed

17. Li, Y.; Liu, K.; Zhang, W.; Wang, Y.; Wang, B.; Wang, Y.; Li, X. Two 3D Ln(III)-mOFs Based on Phosphineoxide Ligand: Synthesis, Structure Luminescent and Photocatalytic Properties. J. Fluoresc. 2023, 33, 2119–2129. https://doi.org/10.1007/s10895-023-03218-y.Search in Google Scholar PubMed

18. Cao, Z.; Yang, F.; Wu, D.; Wu, L.; Liu, L.; Liu, G.; Li, X.; Zheng, X.; Zheng, X.; Qu, D. Supramolecular Aggregates Constructed by Pillar[5]arene-Based Host-Guest Interaction with Aggregation-Induced Emission. Polym. Chem. 2023, 14, 1318–1322; https://doi.org/10.1039/d3py00026e.Search in Google Scholar

19. Li, X.; Yao, C.; Jiang, W. Emission and Energy Transfer Investigation of Non-Conjugated Total Carbon Configuration Between BODIPY and Naphthalimide. J. Chem. Sci. 2023, 135, 65. https://doi.org/10.1007/s12039-023-02181-2.Search in Google Scholar

20. Wang, J.; Gu, X.; Zhang, P.; Huang, X.; Zheng, X.; Chen, M.; Feng, H.; Kwok, R. T. K.; Lam, J. W. Y.; Tang, B. Z. Ionization and Anion-π+ Interaction: A New Strategy for Structural Design of Aggregation-Induced Emission Luminogens. J. Am. Chem. Soc. 2017, 139, 16974–16979. https://doi.org/10.1021/jacs.7b10150.Search in Google Scholar PubMed

21. Desiraju, G. R. The C–H⋯O Hydrogen Bond in Crystals: What is it? Acc. Chem. Res. 1991, 24, 290–296. https://doi.org/10.1021/ar00010a002.Search in Google Scholar

22. Steiner, T. The Hydrogen Bond in the Solid State. Angew. Chem., Int. Ed. 2002, 41, 48–76. https://doi.org/10.1002/1521-3773(20020104)41:1<48::aid-anie48>3.0.co;2-u.10.1002/1521-3773(20020104)41:1<48::AID-ANIE48>3.0.CO;2-USearch in Google Scholar

23. Li, X.; Qian, Q.; Jiang, W. Photo-Induced Fluorochromism of a Star-Shaped Photochromic Dye with 2,4-Dimethylthiazole Attaching to Triangle Terthiophene. J. Fluoresc. 2023, 33, 1907–1915. https://doi.org/10.1007/s10895-023-03196-1.Search in Google Scholar PubMed

24. Ji, G.; Hou, Q.; Jiang, W.; Li, X. Investigating the Properties of Double Triangle Terthiophene Configured Dumbbell-Like Photochromic Dye with Ethyne and 1,3-Butadiene Bridge. J. Fluoresc. 2023, 33, 1495–1503. https://doi.org/10.1007/s10895-023-03171-w.Search in Google Scholar PubMed

25. Li, X.; Zou, Y.; Heo, G.; Son, Y. A. Emission Shift of an Imidazole Bridged Diethylaminocoumarin and Diphenyl. Mol. Cryst. Liq. Cryst. 2020, 704, 48–56. https://doi.org/10.1080/15421406.2020.1741801.Search in Google Scholar

26. Padghan, S. D.; Hu, J. W.; Wang, L. C.; Hsu, Y. H.; Chen, K. Y. Intermolecular C–H⋯O Hydrogen Bond-Induced H-Aggregates for Rapid, Real-Time Detection of Cyanide. Dyes Pigm. 2024, 235, 112567; https://doi.org/10.1016/j.dyepig.2024.112567.Search in Google Scholar

27. Li, X.; Tian, G.; Shao, D.; Xu, Y.; Wang, Y.; Ji, G.; Ryu, J.; Son, Y. A. A BODIPY Based Emission Signal Turn-On Probe Toward Multiple Heavy Metals. Mol. Cryst. Liq. Cryst. 2020, 706, 38–46. https://doi.org/10.1080/15421406.2020.1743436.Search in Google Scholar

28. Liu, Y.; Li, X.; Min, K. S.; Son, Y. A. Emission Behavior of Naphthalimide-Coumarin Cassette. Mol. Cryst. Liq. Cryst. 2018, 662, 139–146; https://doi.org/10.1080/15421406.2018.1466533.Search in Google Scholar

29. Kong, Y.; Liu, X.; Jiang, W.; Li, X. Photochromic Properties of Triangle Terthiophene- and Triphenylamine-Configured Diarylethene Type Dye with Propeller-Like Conformation. Chem. Pap. 2025, https://doi.org/10.1007/s11696-025-03934-8, In press.Search in Google Scholar

30. Janiak, C. A Critical Account on π–π Stacking in Metal Complexes with Aromatic Nitrogen-Containing Ligands. J. Chem. Soc., Dalton Trans. 2000, 21, 3885–3896; https://doi.org/10.1039/b003010o.Search in Google Scholar

31. Li, X.; Liao, M.; Sun, J.; Heo, G.; Son, Y. A. Thiophene Modulated BODIPY Dye as a Light Harvester. Mol. Cryst. Liq. Cryst. 2019, 679, 127–136. https://doi.org/10.1080/15421406.2019.1597557.Search in Google Scholar

32. Li, X.; Guo, X.; Chen, Y.; Cui, T.; Xing, L. Double 3-Ethyl-2,4-Dimethylpyrrole Configured Fluorescent Dye with Fluorine-Boron as the Bridge. J. Fluoresc. 2021, 31, 1797–1803. https://doi.org/10.1007/s10895-021-02819-9.Search in Google Scholar PubMed

33. Liu, Y.; Li, X.; Kim, H.; Son, Y. A. Investigation of Fluorescent Optical Properties of Fluorine-Boron Cored Dye. Mol. Cryst. Liq. Cryst. 2018, 677, 27–33. https://doi.org/10.1080/15421406.2019.1597508.Search in Google Scholar

34. Zheng, X.; Wang, G.; Liu, L.; Li, X.; Xie, P.; Fan, Y.; Cao, Z.; Niu, C.; Tian, D.; Xie, L. Hydrogen-Bonding Induced Multicolor and Thermochromic Emission of Triphenylamines. Chem. Eur. J. 2025, e202500643; https://doi.org/10.1002/chem.202500643, In press.Search in Google Scholar PubMed

35. Qin, X.; Li, H.; Wang, Y.; Li, Y.; Li, X. Conjugated Iminodibenzyl Dyes Incorporating Phenolic Hydroxyl Group and Strong Electron Donating or Accepting Groups for Facilitating ESIPT and Proton Transfer in Six- or Seven-Membered Cycles. J. Fluoresc. 2025, Submission ID dd2c0c4c-ae92-4110-80b2-21fd1356a2c8 (Accepted), In press.Search in Google Scholar

36. Ji, G.; Hou, Q.; Zhang, J.; Li, X. Investigation of Triangle Terthiophene and Hydroxyphenylbenzothiazole Configured Fluorescent Dye with a Triple Bond Bridge. J. Fluoresc. 2023, 33, 153–159. https://doi.org/10.1007/s10895-022-03049-3.Search in Google Scholar PubMed

37. Li, X.; Cai, Q.; Zhang, J.; Kim, H.; Son, Y. A. An “Electron Lock” Toward the Photochromic Activity of Phenylacetylene Appended Bisthienylethene. Mol. Cryst. Liq. Cryst. 2020, 706, 141–149. https://doi.org/10.1080/15421406.2020.1743450.Search in Google Scholar

38. Li, X.; Zhou, Q.; Heo, G.; Son, Y. A. 2,4-Dimethylpyrrole Configured Fluorine-Boron Complexes. Mol. Cryst. Liq. Cryst. 2018, 677, 34–41. https://doi.org/10.1080/15421406.2019.1597509.Search in Google Scholar

39. He, W.; Li, X.; Kim, H.; Son, Y. A. Shifting the Emission of Proton Transfer Fluorescence with Fluorine-Boron as the Rotation Lock. Mol. Cryst. Liq. Cryst. 2020, 704, 41–47. https://doi.org/10.1080/15421406.2020.1741800.Search in Google Scholar

40. Li, X.; Han, Y.; Kim, M. J.; Son, Y. A. Reversed Photochromism Reactivity of Malononitrile Attached Bisthienylthene. Mol. Cryst. Liq. Cryst. 2018, 662, 147–156. https://doi.org/10.1080/15421406.2018.1466534.Search in Google Scholar

41. Li, X.; Wang, Y.; Jia, C.; Kim, H.; Son, Y. A. Photochromic Reactivity Induced by Electron Distribution: Active or Inactive. Mol. Cryst. Liq. Cryst. 2019, 689, 83–91. https://doi.org/10.1080/15421406.2019.1597556.Search in Google Scholar

42. Ji, G.; Hou, Q.; Jiang, W.; Li, X. Investigating the Properties of Triangle Terthiophene and Triphenylamine Configured Propeller-Like Photochromic Dye with Ethyne Bridge. J. Fluoresc. 2025, https://doi.org/10.1007/s10895-023-03557-w, In press.Search in Google Scholar PubMed

43. Li, X.; Liu, X. A Sensitive Probe of Meso-Cyanophenyl Substituted BODIPY Derivative as Fluorescent Chemosensor for the Detection of Multiple Heavy Metal Ions. J. Fluoresc. 2025, https://doi.org/10.1007/s10895-024-03581-4, In press.Search in Google Scholar PubMed

44. Tian, D.; Lin, J.; Mesbah, A.; Zhou, J.; Yang, M.; Gautier, R.; Chen, X. A Core-Shell Model of Polymetallic Hybrid Metal Alides. Chem. Commun. 2024, 60, 12924–12927. https://doi.org/10.1039/d4cc04454a.Search in Google Scholar PubMed

45. Qian, C.; Xie, L.; Liu, L.; Cao, Z.; Tian, D.; Sun, D.; Liu, G.; Guo, Z.; Zheng, X. Anion-Induced Opposite Mechanochromic and Thermochromic Emission Directions of Protonated Hydrazones. Sci. China Mater. 2025, 68, 125–131. https://doi.org/10.1007/s40843–024–3169–8.10.1007/s40843-024-3169-8Search in Google Scholar

46. Liu, Y.; Li, X.; Sun, S.; Ji, G.; Son, Y. A. Crystal Structure of 2,7-Diiodo-1,3,6,8-tetramethyl-bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine, C14H14B2F4I2N4. Z. Kristallogr. New Cryst. Struct. 2020, 235, 371–372. https://doi.org/10.1515/ncrs-2019-0678.Search in Google Scholar

47. He, W.; Liu, Y.; Sun, S.; Ji, G.; Li, X. Crystal Structure of 2-Bromo-1,3,6,8-tetramethylBOPHY (BOPHY = Bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine), C14H15B2BrF4N4. Z. Kristallogr. New Cryst. Struct. 2021, 236, 949–952. https://doi.org/10.1515/ncrs-2021-0163.Search in Google Scholar

48. Liu, Y.; Sun, S.; Ji, G.; Li, X.; Son, Y. A. Crystal Structure of 2-Phenylethynyl-1,3,6,8-tetramethylBOPHY (BOPHY = Bis(Difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene) hydrazine), C22H20B2F4N4. Z. Kristallogr. New Cryst. Struct. 2021, 236, 749–752. https://doi.org/10.1515/ncrs-2021-0074.Search in Google Scholar
Received: 2025-02-17
Accepted: 2025-03-21
Published Online: 2025-04-03
Published in Print: 2025-06-26

© 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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  15. Crystal structure of (4-(4-chlorophenyl)-1H-pyrrole-3-carbonyl)ferrocene, C21H16ClFeNO
  16. The crystal structure of dichlorido(η6-p-cymene)(triphenylarsine)ruthenium(II), C28H29AsCl2Ru
  17. Crystal structure of (Z)-2-hydroxy-N′-(1-(o-tolyl)ethylidene)benzohydrazide, C16H16N2O2
  18. The crystal structure of 10-(1-bromoethyl)-14-(bromomethyl)dibenzo[a, c]acridine, C24H17NBr2
  19. Synthesis and crystal structure of 6-methoxy-7-[(4-methoxyphenyl)methoxy]-2H-1-benzopyran-2-one, C18H16O5
  20. Synthesis and crystal structure of ethyl 4-((4-trifluoromethylbenzyl)amino)benzo, C17H16F3NO2
  21. The crystal structure of (Z)-2-(tert-butyl)-6-(7-(tert-butyl)-5-methylbenzo[d][1,3]oxathiol-2-ylidene)-4-methylcyclohexa-2,4-dien-1-one, C23H28O2S
  22. The crystal structure of (R)-2-aminobutanamide hydrochloride, C4H11ClN2O
  23. Crystal structure of bromido[hydridotris(3-tert-butyl-5-isopropylpyrazolyl)borato-κ3 N,N′,N″]copper(II), C30H52BBrCuN6
  24. Crystal structure of chlorido{hydridotris[3-mesityl-5-methyl-1H-pyrazol-1-yl-κN3]borato}-copper(II) dichloromethane monosolvate
  25. Crystal structure of 4-[3,5-bis(propan-2-yl)-1H-pyrazol-4-yl]pyridine, C14H19N3
  26. Crystal structure of ((4-(4-bromophenyl)-1H-pyrrol-3-yl)methyl)ferrocene, C21H16BrFeNO
  27. Crystal structure of [(4-chlorobenzyl)triphenylphosphonium] dichloridocopper(I), {[C25H21ClP]+[CuCl2]−}n
  28. The crystal structure of {Cu(2,9-diisopropyl-4,7-diphenyl-1,10-phenanthroline)[4,5-bis(diphenylphosphino)-9,9-dimethylxanthene]}+ PF6−·1.5(EtOAC)
  29. Crystal structure of 3,5-bis(t-butyl)-1H-pyrazol-4-amine, C11H21N3
  30. Crystal structure of [(2,4-dichlorobenzyl)triphenylphosphonium] trichloridocopper(II), [C25H20Cl2P]+[CuCl3]−
  31. The crystal structure of dipotassium sulfide, K2S
  32. Crystal structure of (4-(4-methoxyphenyl)-1H-pyrrole-3-carbonyl)ferrocene, C22H19FeNO2
  33. Crystal structure of (E)-6-(4-methylpiperazin-1-yl)-2-(4-(trifluoromethyl)benzylidene)-3, 4-dihydronaphthalen-1(2H)-one, C23H23F3N2O
  34. Crystal structure of (E)-6-morpholino-2-(4-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H20F3NO2
  35. Crystal structure of Ce9Ir37Ge25
  36. The crystal structure of ethyl 6-(2-nitrophenyl)imidazo[2,1-b]thiazole-3-carboxylate, C14H11N3O4S
  37. Crystal structure of (4-(4-isopropylphenyl)-1H-pyrrol-3-yl)(ferrocenyl)methanone, C24H23FeNO
  38. Crystal structure of bis(methylammonium) tetrathiotungstate(VI), (CH3NH3)2[WS4]
  39. Crystal structure of 6,11-dihydro-12H-benzo[e]indeno[1,2-b]oxepin-12-one, C17H12O2
  40. Crystal structure of 3-[(4-phenylpiperidin-1-yl)methyl]-5-(thiophen-2-yl)-2,3-dihydro-1,3,4- oxadiazole-2-thione, C18H19N3OS2
  41. Crystal structure of N-isopropyl-1,8-naphthalimide C15H13NO2
  42. TiNiSi-type EuPdBi
  43. Crystal structure of 1-(p-tolylphenyl)-4-(2-thienoyl)-3-methyl-1H-pyrazol-5-ol, C16H14N2O2S
  44. The crystal structure of 3-(3-carboxypropyl)-2-nitro-1H-pyrrole 1-oxide, C7H9N3O5
  45. The crystal structure of tetraaqua-bis(2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetato-k2O:N)-tetrakis(2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetato-k1N)trizinc(II) hexahydrate C36H52N18O32Zn3
  46. The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 4-hydroxy-3,5-dimethoxybenzoate monohydrate, C25H30FN3O9
  47. Crystal structure of bis(DL-1-carboxy-2-(1H-indol-3-yl)ethan-1-aminium) oxalate — acetic acid (1/2)
  48. Crystal structure of methyl (E)-4-((4-methylphenyl)sulfonamido)but-2-enoate, C12H15NO4S
  49. The crystal structure of actarit, C10H11NO3
  50. The crystal structure of bicyclol, C19H18O9
  51. The crystal structure of topiroxostat, C13H8N6
  52. Crystal structure of 2,2-dichloro-N-methyl-N-(4-p-tolylthiazol-2-yl)acetamide, C13H12Cl2N2OS
  53. Crystal structure of 4-(trifluoromethyl)-7-coumarinyl trifluoromethanesulfonate C11H4F6O5S
  54. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6)-((Z)-N,N′-bis(2-(dimethylamino)phenyl)carbamimidato-κ1N)potassium(I)
  55. Crystal structure of (Z)-2-(5-((4-(dimethylamino)naphthalen-1-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid, C18H16N2O3S2
  56. Crystal structure of (4-fluorobenzyl)triphenylphosphonium bromide, C25H21BrFP
  57. The crystal structure of dichlorido-[6-(pyridin-2-yl)phenanthridine-κ2N, N′]zinc(II)-chloroform (1/1), C19H13N2ZnCl5
  58. Crystal structure of (E)-(3-(2,4-dichlorophenyl)acryloyl)ferrocene, C19H14Cl2FeO
  59. The crystal structure of (E)-7-chloro-1-cyclopropyl-6-fluoro-3-((2-hydroxybenzylidene)amino)quinolin-4(1H)-one, C19H14ClFN2O2
  60. Crystal structure of 2-bromo-11-(((fluoromethyl)sulfonyl)methyl)-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide, C16H13BrFNO4S2
  61. Crystal structure of 2-chloro-11-(((fluoromethyl)sulfonyl)methyl)-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide, C16H13ClFNO4S2
  62. Crystal structure of 5-(2,2-difluoropropyl)-5-methyl-6-oxo-5,6-dihydrobenzo[4,5]imidazo[2,1-a]isoquinoline-3-carbonitrile, C20H15F2N3O
https://doi.org/10.1515/ncrs-2025-0077
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of 5,5′-bis(2,4,6-trinitrophenyl)-2,2′-bi(1,3,4-oxadiazole), C16H4N10O14
  4. Crystal structure of catena-poly[(μ3-4,4′-oxydibenzoato- κ5 O,O′: O″,O‴:O‴)-bis(2,4,6-tri(3-pyridine)-1,3,5-triazine-κ1 N)cadmium(II)], C50H32CdN12O5
  5. The crystal structure of 1,4-diazepane-1,4-diium potassium trinitrate, C5H14KN5O9
  6. The crystal structure of benzyl 2,2,5,5-tetramethylthiazolidine-4-carboxylate, C15H21NO2S
  7. Crystal structure of 2-hydroxyethyl-triphenylphosphonium tetracyanidoborate, C24H20BN4OP
  8. The crystal structure of 1-methyl-3-(N-methylnitrous amide–N-methylene) imidazolidine-2,4,5-trione
  9. Crystal structure of N-((3-cyano-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(2,2,2-trifluoroacetyl)-1H-pyrazol-5-yl)carbamoyl)-2,6-difluorobenzamide, C20H7Cl2F8N5O3S
  10. Crystal structure of 5-(2,2-difluoropropyl)-5-methylbenzo[4,5]imidazo[2,1-a] isoquinolin-6(5H)-one, C20H18F2N2O
  11. The crystal structure of N′,N″-[1,2-bis(4-chlorophenyl)ethane-1,2-diylidene]bis(furan-2- carbohydrazide), C24H16Cl2N4O4
  12. Crystal structure of [(4-bromobenzyl)triphenylphosphonium] tetrabromoantimony(III), [C25H21BrP]+[SbBr4]−
  13. Crystal structure of [(4-bromobenzyl)triphenylphosphonium] tetrabromidoindium(III), [C25H21BrP]+[InBr4]−
  14. The crystal structure of 4-carboxy-2-oxobutan-1-aminium chloride, C5H10ClNO3
  15. Crystal structure of (4-(4-chlorophenyl)-1H-pyrrole-3-carbonyl)ferrocene, C21H16ClFeNO
  16. The crystal structure of dichlorido(η6-p-cymene)(triphenylarsine)ruthenium(II), C28H29AsCl2Ru
  17. Crystal structure of (Z)-2-hydroxy-N′-(1-(o-tolyl)ethylidene)benzohydrazide, C16H16N2O2
  18. The crystal structure of 10-(1-bromoethyl)-14-(bromomethyl)dibenzo[a, c]acridine, C24H17NBr2
  19. Synthesis and crystal structure of 6-methoxy-7-[(4-methoxyphenyl)methoxy]-2H-1-benzopyran-2-one, C18H16O5
  20. Synthesis and crystal structure of ethyl 4-((4-trifluoromethylbenzyl)amino)benzo, C17H16F3NO2
  21. The crystal structure of (Z)-2-(tert-butyl)-6-(7-(tert-butyl)-5-methylbenzo[d][1,3]oxathiol-2-ylidene)-4-methylcyclohexa-2,4-dien-1-one, C23H28O2S
  22. The crystal structure of (R)-2-aminobutanamide hydrochloride, C4H11ClN2O
  23. Crystal structure of bromido[hydridotris(3-tert-butyl-5-isopropylpyrazolyl)borato-κ3 N,N′,N″]copper(II), C30H52BBrCuN6
  24. Crystal structure of chlorido{hydridotris[3-mesityl-5-methyl-1H-pyrazol-1-yl-κN3]borato}-copper(II) dichloromethane monosolvate
  25. Crystal structure of 4-[3,5-bis(propan-2-yl)-1H-pyrazol-4-yl]pyridine, C14H19N3
  26. Crystal structure of ((4-(4-bromophenyl)-1H-pyrrol-3-yl)methyl)ferrocene, C21H16BrFeNO
  27. Crystal structure of [(4-chlorobenzyl)triphenylphosphonium] dichloridocopper(I), {[C25H21ClP]+[CuCl2]−}n
  28. The crystal structure of {Cu(2,9-diisopropyl-4,7-diphenyl-1,10-phenanthroline)[4,5-bis(diphenylphosphino)-9,9-dimethylxanthene]}+ PF6−·1.5(EtOAC)
  29. Crystal structure of 3,5-bis(t-butyl)-1H-pyrazol-4-amine, C11H21N3
  30. Crystal structure of [(2,4-dichlorobenzyl)triphenylphosphonium] trichloridocopper(II), [C25H20Cl2P]+[CuCl3]−
  31. The crystal structure of dipotassium sulfide, K2S
  32. Crystal structure of (4-(4-methoxyphenyl)-1H-pyrrole-3-carbonyl)ferrocene, C22H19FeNO2
  33. Crystal structure of (E)-6-(4-methylpiperazin-1-yl)-2-(4-(trifluoromethyl)benzylidene)-3, 4-dihydronaphthalen-1(2H)-one, C23H23F3N2O
  34. Crystal structure of (E)-6-morpholino-2-(4-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H20F3NO2
  35. Crystal structure of Ce9Ir37Ge25
  36. The crystal structure of ethyl 6-(2-nitrophenyl)imidazo[2,1-b]thiazole-3-carboxylate, C14H11N3O4S
  37. Crystal structure of (4-(4-isopropylphenyl)-1H-pyrrol-3-yl)(ferrocenyl)methanone, C24H23FeNO
  38. Crystal structure of bis(methylammonium) tetrathiotungstate(VI), (CH3NH3)2[WS4]
  39. Crystal structure of 6,11-dihydro-12H-benzo[e]indeno[1,2-b]oxepin-12-one, C17H12O2
  40. Crystal structure of 3-[(4-phenylpiperidin-1-yl)methyl]-5-(thiophen-2-yl)-2,3-dihydro-1,3,4- oxadiazole-2-thione, C18H19N3OS2
  41. Crystal structure of N-isopropyl-1,8-naphthalimide C15H13NO2
  42. TiNiSi-type EuPdBi
  43. Crystal structure of 1-(p-tolylphenyl)-4-(2-thienoyl)-3-methyl-1H-pyrazol-5-ol, C16H14N2O2S
  44. The crystal structure of 3-(3-carboxypropyl)-2-nitro-1H-pyrrole 1-oxide, C7H9N3O5
  45. The crystal structure of tetraaqua-bis(2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetato-k2O:N)-tetrakis(2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetato-k1N)trizinc(II) hexahydrate C36H52N18O32Zn3
  46. The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 4-hydroxy-3,5-dimethoxybenzoate monohydrate, C25H30FN3O9
  47. Crystal structure of bis(DL-1-carboxy-2-(1H-indol-3-yl)ethan-1-aminium) oxalate — acetic acid (1/2)
  48. Crystal structure of methyl (E)-4-((4-methylphenyl)sulfonamido)but-2-enoate, C12H15NO4S
  49. The crystal structure of actarit, C10H11NO3
  50. The crystal structure of bicyclol, C19H18O9
  51. The crystal structure of topiroxostat, C13H8N6
  52. Crystal structure of 2,2-dichloro-N-methyl-N-(4-p-tolylthiazol-2-yl)acetamide, C13H12Cl2N2OS
  53. Crystal structure of 4-(trifluoromethyl)-7-coumarinyl trifluoromethanesulfonate C11H4F6O5S
  54. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6)-((Z)-N,N′-bis(2-(dimethylamino)phenyl)carbamimidato-κ1N)potassium(I)
  55. Crystal structure of (Z)-2-(5-((4-(dimethylamino)naphthalen-1-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid, C18H16N2O3S2
  56. Crystal structure of (4-fluorobenzyl)triphenylphosphonium bromide, C25H21BrFP
  57. The crystal structure of dichlorido-[6-(pyridin-2-yl)phenanthridine-κ2N, N′]zinc(II)-chloroform (1/1), C19H13N2ZnCl5
  58. Crystal structure of (E)-(3-(2,4-dichlorophenyl)acryloyl)ferrocene, C19H14Cl2FeO
  59. The crystal structure of (E)-7-chloro-1-cyclopropyl-6-fluoro-3-((2-hydroxybenzylidene)amino)quinolin-4(1H)-one, C19H14ClFN2O2
  60. Crystal structure of 2-bromo-11-(((fluoromethyl)sulfonyl)methyl)-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide, C16H13BrFNO4S2
  61. Crystal structure of 2-chloro-11-(((fluoromethyl)sulfonyl)methyl)-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide, C16H13ClFNO4S2
  62. Crystal structure of 5-(2,2-difluoropropyl)-5-methyl-6-oxo-5,6-dihydrobenzo[4,5]imidazo[2,1-a]isoquinoline-3-carbonitrile, C20H15F2N3O
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