Home Crystal structure of acrinidinium tetrafluorohydrogenphthalate, C21H11F4NO4
Article Open Access

Crystal structure of acrinidinium tetrafluorohydrogenphthalate, C21H11F4NO4

  • Xin-Fang Liu ORCID logo EMAIL logo , Jun-Ya Song , Bei-Bei Zhao and Shi-Jie Huang
Published/Copyright: May 20, 2022
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 237 Issue 4

Abstract

C21H11F4NO4, triclinic, P 1 ‾ (no. 2), a = 9.5000(4) Å, b = 13.9989(7) Å, c = 14.1423(5) Å, α = 91.355(4)°, β = 108.542(4)°, γ = 98.958(4)°, V = 1756.02(14) Å3, Z = 4, R gt (F) = 0.0494, wR ref (F 2) = 0.1157, T = 293(2) K.

CCDC no.: 2151627

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: Orange block
Size: 0.21 × 0.20 × 0.20 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.14 mm−1
Diffractometer, scan mode: SuperNova, ω
θ max, completeness: 29.3°, >99%
N(hkl)measured, N(hkl)unique, R int: 15,149, 8030, 0.020
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 5734
N(param)refined: 543
Programs: CrysAlisPRO [1], Olex2 [2], SHELX [3,4]
Table 2:

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

Atom x y z U iso*/U eq
F1 0.69627 (15) 1.12057 (9) −0.00684 (9) 0.0559 (3)
F2 0.82500 (14) 1.00955 (10) −0.09927 (8) 0.0531 (3)
F3 0.90785 (15) 0.84375 (10) −0.02169 (9) 0.0576 (4)
F4 0.87001 (13) 0.79328 (8) 0.14903 (9) 0.0487 (3)
O1 0.71524 (15) 1.16530 (10) 0.19803 (10) 0.0413 (3)
H1B 0.6631 1.2044 0.2057 0.062*
O2 0.50202 (15) 1.05756 (11) 0.16415 (11) 0.0484 (4)
O3 0.72255 (16) 0.96539 (10) 0.31652 (9) 0.0410 (3)
O4 0.70463 (19) 0.81013 (10) 0.27344 (10) 0.0533 (4)
C14 0.74873 (19) 0.92731 (13) 0.16122 (12) 0.0296 (4)
C15 0.70823 (19) 1.01367 (13) 0.12094 (12) 0.0295 (4)
C16 0.7354 (2) 1.03931 (14) 0.03400 (13) 0.0361 (4)
C17 0.8004 (2) 0.98272 (16) −0.01483 (13) 0.0383 (5)
C18 0.8416 (2) 0.89931 (15) 0.02424 (14) 0.0380 (5)
C19 0.8176 (2) 0.87294 (14) 0.11191 (13) 0.0339 (4)
C20 0.7232 (2) 0.89721 (14) 0.25773 (13) 0.0313 (4)
C21 0.6295 (2) 1.07989 (14) 0.16496 (12) 0.0327 (4)
F5 0.14775 (18) 0.39433 (10) 0.95474 (12) 0.0776 (5)
F6 0.17855 (19) 0.53081 (11) 1.09996 (11) 0.0798 (5)
F7 0.34957 (17) 0.70678 (10) 1.10945 (8) 0.0659 (4)
F8 0.48495 (14) 0.74706 (9) 0.97145 (8) 0.0517 (3)
O5 0.34896 (16) 0.35423 (10) 0.83519 (10) 0.0457 (4)
H5A 0.3167 0.3054 0.7963 0.069*
O6 0.18248 (19) 0.42105 (13) 0.71838 (11) 0.0651 (5)
O7 0.50219 (17) 0.55649 (11) 0.77185 (11) 0.0501 (4)
O8 0.42477 (17) 0.69855 (10) 0.76425 (10) 0.0471 (4)
N1 0.59769 (16) 0.90183 (11) 0.44963 (10) 0.0310 (3)
H1 0.6355 0.9193 0.4037 0.037*
C1 0.8498 (2) 0.90658 (14) 0.55949 (14) 0.0382 (5)
H1A 0.8890 0.9246 0.5088 0.046*
C2 0.9432 (2) 0.89492 (15) 0.65227 (16) 0.0442 (5)
H2 1.0467 0.9046 0.6645 0.053*
C3 0.8857 (2) 0.86837 (16) 0.73020 (15) 0.0469 (5)
H3 0.9518 0.8615 0.7932 0.056*
C4 0.7362 (2) 0.85288 (15) 0.71450 (14) 0.0413 (5)
H4 0.7001 0.8350 0.7665 0.050*
C5 0.2219 (2) 0.84377 (15) 0.47590 (16) 0.0442 (5)
H5 0.1769 0.8273 0.5242 0.053*
C6 0.1349 (2) 0.85265 (17) 0.38120 (18) 0.0524 (6)
H6 0.0305 0.8409 0.3645 0.063*
C7 0.2016 (2) 0.87969 (16) 0.30746 (17) 0.0510 (6)
H7 0.1399 0.8856 0.2428 0.061*
C8 0.3527 (2) 0.89718 (14) 0.32853 (14) 0.0409 (5)
H8 0.3946 0.9159 0.2793 0.049*
C9 0.4779 (2) 0.84906 (14) 0.59706 (13) 0.0358 (4)
H9 0.4373 0.8319 0.6473 0.043*
C10 0.6334 (2) 0.86367 (13) 0.61889 (13) 0.0323 (4)
C11 0.6931 (2) 0.89095 (13) 0.54115 (13) 0.0298 (4)
C12 0.4461 (2) 0.88672 (13) 0.42639 (13) 0.0306 (4)
C13 0.3820 (2) 0.85944 (13) 0.50230 (14) 0.0324 (4)
N2 0.57485 (17) 0.60620 (11) 0.61271 (11) 0.0324 (3)
H2A 0.5481 0.5902 0.6636 0.039*
C22 0.3122 (2) 0.59166 (15) 0.51758 (16) 0.0425 (5)
H22 0.2843 0.5728 0.5726 0.051*
C23 0.2055 (3) 0.59900 (16) 0.42848 (18) 0.0541 (6)
H23 0.1042 0.5849 0.4231 0.065*
C24 0.2453 (3) 0.62744 (17) 0.34429 (18) 0.0597 (7)
H24 0.1702 0.6323 0.2844 0.072*
C25 0.3909 (3) 0.64765 (16) 0.34940 (15) 0.0521 (6)
H25 0.4154 0.6662 0.2931 0.063*
C26 0.9263 (3) 0.66317 (17) 0.5534 (2) 0.0562 (6)
H26 0.9594 0.6793 0.4997 0.067*
C27 1.0271 (3) 0.65335 (19) 0.6427 (2) 0.0654 (7)
H27 1.1291 0.6623 0.6499 0.079*
C28 0.9799 (3) 0.62975 (18) 0.7250 (2) 0.0612 (7)
H28 1.0515 0.6241 0.7863 0.073*
C29 0.8314 (2) 0.61495 (15) 0.71700 (16) 0.0462 (5)
H29 0.8018 0.5995 0.7722 0.055*
C30 0.6602 (2) 0.65850 (14) 0.45079 (15) 0.0430 (5)
H30 0.6893 0.6770 0.3961 0.052*
C31 0.5079 (2) 0.64085 (14) 0.44057 (13) 0.0371 (4)
C32 0.4660 (2) 0.61307 (13) 0.52530 (13) 0.0327 (4)
C33 0.7231 (2) 0.62325 (13) 0.62397 (14) 0.0333 (4)
C34 0.7697 (2) 0.64919 (14) 0.54046 (15) 0.0383 (5)
C35 0.3776 (2) 0.59317 (14) 0.88412 (12) 0.0315 (4)
C36 0.2951 (2) 0.50102 (14) 0.88244 (13) 0.0353 (4)
C37 0.2308 (3) 0.48186 (16) 0.95586 (16) 0.0471 (5)
C38 0.2459 (3) 0.55112 (18) 1.03069 (15) 0.0507 (6)
C39 0.3301 (3) 0.64016 (16) 1.03478 (14) 0.0458 (5)
C40 0.3965 (2) 0.66066 (14) 0.96212 (13) 0.0366 (4)
C41 0.4416 (2) 0.61909 (14) 0.80056 (13) 0.0333 (4)
C42 0.2695 (2) 0.42142 (15) 0.80113 (15) 0.0379 (4)

Source of material

A 3 mL EtOH solution of tetrafluorophthalic acid (TFPA, 23.8 mg, 0.1 mmol) was slowly added into a 3 mL EtOH solution of acridine (AD, 17.9 mg, 0.1 mmol) in a 50 mL beaker. The mixture was stirred for 5 min at room temperature. Orange block crystals of the title compound were obtained after about 10 h (CCDC number 2151627).

Experimental details

Empirical absorption correction was performed using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Using Olex2 [2], the structure was solved with the ShelXT [3] structure solution program and refined with the ShelXL [4] refinement package.

The carbon bound hydrogen atoms were placed in calculated positions and refined using a riding model.

Comment

Over the past few decades, the rational design and synthesis of luminescent materials have attracted great attention due to their excellent performance in several fields. Among them, two-component crystal materials, assembled by two or more different molecules assembled through hydrogen bond, π–π or charge transfer interactions, have been favored by scientific researchers because of its simple synthetic route, and versatile molecular arrangement [5], [6], [7], [8], [9]. It is well known that acrinidine (AD) is an excellent chromophore and fluorinated organic ligand can enhance the luminescence intensity of complex [10], [11], [12]. In this work, AD was used as the electron acceptor to react with TFPA, and a complex salt was constructed by forming intermolecular hydrogen bonds.

The asymmetric unit of the title compound consists of two molecules of TFPA anions and two molecules of AD cations. As shown in the figure, one of the carboxyl groups of TFPA is deprotonated and the proton is transfered to the nitrogen atom of AD, and the proton transfer is proved by the comparable C–O bond lengths (C20–O3, 1.253(2) Å; C20–O4, 1.240(2) Å) in the carboxyl group [13,14]. Bond lengths and angles in all ions are in the expected ranges [15,16]. Each AD cation is hydrogen bonded to a TFPA anion by N–H⃛O hydrogen bond to form a TFPA-AD ion pair, which is further linked by the O–H⃛O hydrogen bonds and π–π interactions into a 3D supramolecular structure. From another perspective, the TFPA anions located adjacent to each other are connected through O–H⃛O hydrogen bonds, forming an infinite 1D chain along the b direction, and the AD cations are fixed together by multiple TFPA chains in an antiparallel packing manner through N–H⃛O hydrogen bonds and π–π interactions, forming a 3D supramolecular structure.

Corresponding author: Xin-Fang Liu, College of Chemistry and Chemical Engineering, Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Normal University, Luoyang, Henan 471934, P. R. China, E-mail:

Funding source: Training Program for Young Cadre Teachers of Higher Education Institutions in Henan Province

Award Identifier / Grant number: 2018GGJS128

Funding source: Science and Technology Development Project in Henan Province

Award Identifier / Grant number: 172101410037

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

  2. Research funding: This work was supported by the Training Program for Young Cadre Teachers of Higher Education Institutions in Henan Province (No. 2018GGJS128) and Science and Technology Development Project in Henan Province (No. 172101410037).

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

References

1. Oxford Diffraction Ltd. CrysAlisPRO (version 1.171.39.6a); Rigaku Oxford Diffraction: England, 2018.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. SHELXTL – integrated space-group and crystal-structure determination. Acta Crystallogr. 2015, A71, 3–8; https://doi.org/10.1107/s2053273314026370.Search in Google Scholar PubMed PubMed Central

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

5. Li, S. Z., Yan, D. P. Two-component aggregation-induced emission: two-component aggregation-induced emission materials: tunable one/two-photon luminescence and stimuli-responsive switches by co-crystal formation. Adv. Opt. Mater. 2018, 6, 1870076; https://doi.org/10.1002/adom.201870076.Search in Google Scholar

6. Yang, X. G., Zhai, Z. M., Lu, X. M., Ma, L. F., Yan, D. Fast crystallization-deposition of orderly molecule level heterojunction thin films showing tunable up-conversion and ultrahigh photoelectric response. ACS Cent. Sci. 2020, 6, 1169–1178; https://doi.org/10.1021/acscentsci.0c00447.Search in Google Scholar PubMed PubMed Central

7. Khan, A., Wang, M., Usman, R., Sun, H., Du, M., Xu, C. Molecular marriage via charge transfer interaction in organic charge transfer co-crystals toward solid-state fluorescence modulation. Cryst. Growth Des. 2017, 17, 1251–1257; https://doi.org/10.1021/acs.cgd.6b01636.Search in Google Scholar

8. Mandal, A., Kim, Y., Kim, S. J., Park, J. H. Unravelling the fluorescence and semiconductor properties of a new coronene: TCNB charge transfer cocrystal polymorph. CrystEngComm 2021, 23, 7132–7140; https://doi.org/10.1039/d1ce00741f.Search in Google Scholar

9. Wang, Y., Shang, H., Li, B., Jiang, S. Reversible luminescence “off–on” regulation based on tunable photodimerization via crystal-to-cocrystal transformation. J. Mater. Chem. C 2022, 10, 734–741; https://doi.org/10.1039/d1tc04401j.Search in Google Scholar

10. Varaksina, E. A., Kiskin, M. A., Lyssenko, K. A., Puntus, L. N., Korshunov, V. M., Silva, G. S., Freiref, R. O., Taydakov, I. V. Tuning the luminescence efficiency by perfluorination of side chains in Eu3+ complexes with β-diketones of the thiophene series. Phys. Chem. Chem. Phys. 2021, 23, 25748–25760; https://doi.org/10.1039/d1cp02951g.Search in Google Scholar PubMed

11. Yao, X., Wang, X., Han, Y., Yan, P., Li, Y., Li, G. Structure, color-tunable luminescence, and uv-vis/nir benzaldehyde detection of lanthanide coordination polymers based on two fluorinated ligands. CrystEngComm 2018, 20, 3335–3343; https://doi.org/10.1039/c8ce00516h.Search in Google Scholar

12. Devi, R., Bala, M., Khatkar, S. P., Taxak, V. B., Boora, P. Investigations of luminescent behavior and intramolecular energy transfer mechanism of Europium(III) complexes with fluorinated β-ketoester ligand. J. Fluor. Chem. 2006, 181, 36–44.10.1016/j.jfluchem.2015.11.004Search in Google Scholar

13. Sedghiniya, S., Soleimannejad, J., Janczak, J. The salt-cocrystal spectrum in salicylic acid-adenine: the influence of crystal structure on proton-transfer balance. Acta Crystallogr. 2019, C75, 412–421; https://doi.org/10.1107/s2053229619003127.Search in Google Scholar PubMed

14. D’Vries, R. F., Moreno-Fuquen, R., Camps, I., Ayala, A. P., Kennedy, A. R., Ellena, J. Order-disorder phase transition induced by proton transfer in a co-crystal of 2,4-dichlorobenzoic acid and trimethylamine n-oxide. CrystEngComm 2017, 19, 3753–3759; https://doi.org/10.1039/c7ce00835j.Search in Google Scholar

15. Chang, X. Crystal structure of bis(acridin-10-ium) 2,5-dihydroxy terephthalate-2,5-dihydroxyterephthalic acid (1/1), C21H15NO6. Z. Kristallogr. N. Cryst. Struct. 2019, 234, 1253–1254; https://doi.org/10.1515/ncrs-2019-0377.Search in Google Scholar

16. Häcker, H.-G., Schnakenburg, G., Hoffbauer, W., Daniels, J., Pietsch, M., Gütschow, M. Isopropylammonium tetrafluorohydrogenphthalate: structural characterization and comparison to two related salts with different stoichiometric ratios. J. Mol. Struct. 2009, 934, 23–27; https://doi.org/10.1016/j.molstruc.2009.06.013.Search in Google Scholar
Received: 2022-02-19
Accepted: 2022-05-05
Published Online: 2022-05-20
Published in Print: 2022-08-26

© 2022 Xin-Fang Liu et al., 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. Crystal structure of N-((3s,5s,7s)-adamantan-1-yl)-2-(3-benzoylphenyl)propanamide, C26H29NO2
  4. The crystal structure of bis(μ2-5-chloro-2-oxido-N-(1-oxidopropylidene)benzohydrazonato-κ5 N,O,O′:N′,O′′)-octakis(pyridine-κ1 N)trinickel(II) C60H56Cl2N12Ni3O6
  5. The crystal structure of 3-(4-chlorophenyl)-1,5-di-p-tolylpentane-1,5-dione, C25H23ClO2
  6. The crystal structure of 2,4,4-triphenyl-4H-benzo[b][1,4]oxaphosphinin-4-ium bromide – dichloromethane (1/1), C27H22BrCl2OP
  7. The crystal structure of 2-(3,6-di-tert-butyl-1,8-diiodo-9H-carbazol-9-yl)acetonitrile, C22H24I2N2
  8. Crystal structure of 3-phenylpropyl 2-(6-methoxynaphthalen-2-yl)propanoate, C23H24O3
  9. The crystal structure of (4-fluorophenyl)(5-(hydroxymethyl)furan-2-yl)methanol, C12H11FO3
  10. Crystal structure of the dihydrate of tetraethylammonium 1,3,5-thiadiazole-5-amido-2-carbamate, C11H27N5O4S
  11. Crystal structure of (Z)-4-[(p-tolylamino)(furan-2-yl)methylene]-3-phenyl-1-1-p-tolyl-1H-phenyl-1H-pyrazol-5(4H)-one, C28H23N3O2
  12. The crystal structure of (E)-3-(2-chlorophenyl)-1-ferrocenylprop-2-en-1-one, C19H15ClFeO
  13. The pseudosymmetric crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium hexachloridostannate(IV), C10H16N2SnCl6
  14. Crystal structure of (2-(1-hydroxyheptyl)octahydro-8aH-chromene-5,8,8a-triol), C16H30O5
  15. The crystal structure of N-cyclohexyl-3-hydroxy-4-methoxybenzamide, C14H19NO3
  16. Crystal structure of 1-(4-hydroxybenzyl)-4-methoxy-9,10-dihydrophenanthrene-2,7-diol from Arundina graminifolia, C22H20O4
  17. The crystal structure of N-cyclopentyl-3-hydroxy-4-methoxybenzamide, C13H17NO3
  18. The crystal structure of 2,5,5-triphenyl-3,5-dihydro-4H-imidazol-4-one, C21H16N2O
  19. Crystal structure of 1H-1,2,3-Triazolo[4,5-b]-pyridin-4-ium nitrate, C5H5N5O3
  20. Crystal structure of (Z)-4-(((4-bromophenyl)amino)(furan-2-yl)methylene)-2,5-diphenyl-2,4-dihydro-3H-pyrazol-3-one, C26H18BrN3O2
  21. Crystal structure of 2-(4-methoxyphenyl)-3-methyl-1,8-naphthyridine, C16H14N2O
  22. The crystal structure of 3-([1,1′-biphenyl]-2-yl)-1,2-diphenylbenzo[b]phosphole-1-oxide, C32H23OP
  23. The crystal structure of ammonium (E)-4-((4-carboxyphenyl)diazenyl)benzoate, C14H13N3O4
  24. Crystal structure of bis(5-amino-1,2,4-triazol-4-ium-3-yl)methane sulfate, C5H10N8O4S
  25. The crystal structure of phenantroline-κ2 N,N′-bis(6-phenylpyridine-2-carboxylato-κ2 N,O)copper(II), C36H24N4O4Cu
  26. The crystal structure of tris(6-methylpyridin-2-yl)phosphine oxide, C18H18N3OP
  27. The crystal structure of N-(2′-hydroxymethyl-5′-phenyl-3′,4′-dihydro-[1,1′:3′,1″-terphenyl]- 1′(2′H)-yl)-P,P-diphenylphosphinic amide, C37H34NO2P
  28. Crystal structure of (E)-4-(6-(4-(2-(pyridin-4-yl)vinyl)phenoxy)pyrimidin-4-yl)morpholine, C21H20N4O2
  29. Crystal structure of 5-(adamantan-1-yl)-3-[(4-trifluoromethylanilino)methyl]-2,3-dihydro-1,3,4-oxadiazole-2-thione, C20H22F3N3OS
  30. Crystal structure of 2,2-dichloro-1-(4-chloro-1H-indol-1-yl)ethan-1-one, C10H6Cl3NO
  31. The crystal structure of 4-(((3-bromo-5-(trifluoromethyl)pyridin-2-yl)oxy)methyl)benzonitrile, C28H16Br2F6N4O2
  32. The crystal structure of 1H-benzimidazole-2-carboxamide, C8H7N3O
  33. The crystal structure of Histidinium hydrogensquarate, C10H11N3O6
  34. The crystal structure of 3-amino-5-carboxypyridin-1-ium iodide, C6H7IN2O2
  35. Crystal structure of (E)-amino(2-(3-ethoxy-4-hydroxybenzylidene)hydrazineyl)methaniminium nitrate hemihydrate C10H16N5O5.5
  36. Crystal structure of 1,2-bis(4,5-dinitro-1H-imidazol-1-yl)ethane, C8H6N8O8
  37. The crystal structure of diaqua-bis(pyrazolo[1,5-a]pyrimidine-3-carboxylato-κ2N,O)manganese(II), C14H12N6O6Mn
  38. The crystal structure of catena-poly[aqua-2,2′bipyridine-κ2N,N′-(μ2-5-ethoxyisophthalato-κ 4O,O′:Oʺ,O′ʺ)cadmium(II)] monohydrate, C20H20CdN2O7
  39. The crystal structure of (1S,3R)-1-(4-isopropylphenyl)-3-(methoxycarbonyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-iumchloride monohydrate, C22H27ClN2O3
  40. Crystal structure of 1-isopropyl-3-(prop-1-en-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, C11H15N5
  41. The crystal structure of (2,2′-bipyridine-κ2N,N′)- bis(6-phenylpyridine-2-carboxylate-κ2N,O)manganese(II)] monohydrate, C34H26N4O5Mn
  42. Crystal structure of the cocrystal 1,3,5,7-tetranitro-1,3,5,7-tetrazoctane ─ 2,3-dihydroindole (1/1), C12H17N9O8
  43. Crystal structure of 3-acetyl-6-hydroxy-2H-chromen-2-one monohydrate, C11H10O5
  44. Crystal structure of 6,9-diamino-2-ethoxyacridinium 3,5-dinitrobenozate — dimethylsulfoxide — water (1/1/1), C24H27N5O9S
  45. The crystal structure of 4,4′-bipyridinium bis-(2-hydroxy-3-methoxybenzoate), 2(C8H7.68O4)·C10H8.64N2
  46. Crystal structure of (Z)-4-(((4-fluorophenyl)amino)(furan-2-yl)methylene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one
  47. The crystal structure of bis(4-chloro-2-(((2-chloroethyl)imino)methyl)phenolato-κ2N,O)-oxidovanadium(IV), C18H16Cl4N2O3V
  48. The crystal structure of 17-(bromoethynyl)-17-hydroxy-10, 13-dimethyl- 1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one, C21H27BrO2
  49. The crystal structure of 4-((6-fluoropyridin-2-yloxy)methyl)benzonitrile, C13H9FN2O
  50. Crystal structure of (Z)-2-(1-bromo-2-phenylvinyl)-5-ethyl-2-methyl-1,3-dioxane-5-carboxylic acid, C15H17Br1O4
  51. Crystal structure of catena-poly[tribenzyl-κ1C-(μ2-6-oxidopyridin-1-ium-3-carboxylato-κ2O:O’)tin(IV)-dichloromethane-methanol (1/1/1), C29H31Cl2NO4Sn
  52. Crystal structure of bis{2-(tert-butyl)-6-((E)-((4-((E)-1-(methoxyimino)ethyl)phenyl)imino)methyl)phenolato-κ2N,O}zinc(II), C40H46N4O4Zn
  53. Crystal structure of diaqua-bis(μ2-2-carboxy-3,4,5,6-tetrafluorobenzoato-κ2O:O′)-bis(phenanthroline-κ2N,N′)-bis(μ2-3,4,5,6-tetrafluorophthalato-κ3O:O,O′)dieuropium(III) – phenanthroline (1/2), C40H19EuF8N4O9
  54. The crystal structure of diaqua-bis(6-phenylpyridine-2-carboxylato-κ2N,O) manganese(II) — water — dimethylformamide (1/2/1), C27H31N3O9Mn
  55. The crystal structure of bis(pyrazolo[1,5-a]pyrimidine-3-carboxylato-κ2N,O)-copper(ii), C14H8N6O4Cu
  56. Crystal structure of poly[(μ2-1-(1-imidazolyl)-4-(imidazol-1-ylmethyl)benzene-κ2N:N′)-(μ3-pyridazine-4,5-dicarboxylate-κ3O:O′:N)]copper(II) hydrate, C19H16CuN6O5
  57. Crystal structure of acrinidinium tetrafluorohydrogenphthalate, C21H11F4NO4
  58. Crystal structure of 2-(1H-pyrazol-3-yl-κN)pyridine-κN-bis(2-(2,4-difluorophenyl)pyridinato-κ2C,N)iridium(III) sesquihydrate, C30H18F4IrN5·1.5[H2O]
  59. Crystal structure of 2-(2-hydroxy-5-nitrophenyl)-5-methyl-1,3-dioxane-5-carboxylic acid, C12H13N1O7
  60. The crystal structure of 1,2-bis(pyridinium-4-yl)ethane diperchlorate, C12H14N2·2ClO4 – a second polymorph
  61. The crystal structure of [(1,10-phenantroline-κ2N,N′)-bis(6-phenylpyridine-2-carboxylato-κ2N,O)manganese(II)] monohydrate, C36H26N4O5Mn
  62. Crystal structure of 1,2-bis(2,2,3,3,5,5,5-heptamethyl-1,1,4,4- tetrakis(trimethylsilyl)pentasilan-1-yl)ditellane, C38H114Si18Te2
  63. Crystal structure of 1,2-bis(2,4-dinitro-1H-imidazol-1-yl)ethane – dimethylformamide (1/1), C11H13N9O9
  64. Crystal structure of (Z)-3-((tert-butylamino) methylene)-2-(2-hydroxynaphthalen-1-yl) chroman-4-one, C24H23NO3
  65. Synthesis and crystal structure of (E)-1-(4-(((E)-3-(tert-butyl)-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-ethyl oxime, C21H26N2O2
  66. Crystal structure of the double salt bis(5-amino-1,2,4-triazol-4-ium-3-yl)methane hydrogen oxalate hemioxalate, C8H11N8O6
  67. Hydrothermal synthesis and crystal structure of catena-poly[diaqua-bis(μ2-4-[(4-pyridinylmethyl)amino]benzoato-κ2N:O)cobalt(II)]–1,2bi(4-pyridyl)ethene–water (1/1/1), C50H50N8O8Co
  68. Crystal structure of 3-(3-bromophenyl)-1′,3′-dimethyl-2′H,3H,4H-spiro[furo[3, 2-c]chromene-2,5′-pyrimidine]-2′,4,4′,6′(1′H,3′H) tetraone, C22H15BrN2O6
  69. The crystal structure of poly[aqua-(μ2-4,4′- bis(imidazolyl)biphenyl-κ2N:N′)-(μ2-3-nitrobenzene-1,2-dicarboxylato-κ2O:O′)]copper (II) hydrate, C26H21N5O8Cu
  70. The crystal structure of bis(4-(6-carboxy-8-ethyl-3-fluoro-5-oxo-5,8-dihydro-1,8-naphthyridin-2- yl)piperazin-1-ium) adipate tetrahydrate, C36H52F2N8O14
  71. Synthesis and crystal structure of poly[aqua(μ4-(1R,2S,4R)-4-hydroxy-1-((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)pyrrolidin-1-ium-2-carboxylate-κ4O:O′:O″:O‴)sodium(I)] monohydrate, C21H22NNaO12S
  72. Crystal structure of chlorido-(η6-toluene)(2,2′-bipyridine-κ2N,N′)ruthenium(II) hexafluorophosphate, C17H16ClN2RuPF6
  73. The crystal structure of (R)-6-hydroxy-8-methoxy-3-methylisochroman-1-one, C11H12O4
  74. Crystal structure of catena-poly[(5,5,7,12,12,14-hexamethyl -1,4,8,11-tetraazacyclotetradecane- κ4N,N′,Nʺ,N‴)nickel(II)-(μ2-perchlorato-κ2O:O′)] 3,5-dicarboxybenzoate – methanol (1/2), C27H49ClN4NiO12
  75. The crystal structure of 4-(chloromethyl)benzonitrile, C8H6ClN
  76. The crystal structure of dimethylammonium 8-[(7,9-dioxo-6,10-dioxaspiro[4.5]decan-8-ylidene)methyl]-9-oxo-6,10-dioxaspiro[4.5]dec-7-en-7-olate, C19H25NO8
  77. Crystal structure of (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-((1-acetyl-5-bromo-4-chloro-1H-indol-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate hemihydrate C24H25BrClNO11
  78. The crystal structure of the co-crystal tetrakis[2-(tris(4-methoxyphenyl)stannyl)ethyl]silane – tetrahydrofuran – toluene – tetrahydrofurane (1/1/1), C103H116O13SiSn4
  79. Crystal structure of methyl 3-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)propanoate, C16H13NO4
  80. Crystal structure of ethyl (Z)-3-amino-2-cyano-3-(2-oxo-2H-chromen-3-yl)acrylate, C15H12N2O4
  81. Crystal structure of methyl 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetate, C15H11NO4
  82. Crystal structure of catena-poly[diaqua-bis(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)cobalt(II)] tetrafluoroterephthalate, C26H28N8O6F4Co
https://doi.org/10.1515/ncrs-2022-0081
Creative Commons
BY 4.0

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of N-((3s,5s,7s)-adamantan-1-yl)-2-(3-benzoylphenyl)propanamide, C26H29NO2
  4. The crystal structure of bis(μ2-5-chloro-2-oxido-N-(1-oxidopropylidene)benzohydrazonato-κ5 N,O,O′:N′,O′′)-octakis(pyridine-κ1 N)trinickel(II) C60H56Cl2N12Ni3O6
  5. The crystal structure of 3-(4-chlorophenyl)-1,5-di-p-tolylpentane-1,5-dione, C25H23ClO2
  6. The crystal structure of 2,4,4-triphenyl-4H-benzo[b][1,4]oxaphosphinin-4-ium bromide – dichloromethane (1/1), C27H22BrCl2OP
  7. The crystal structure of 2-(3,6-di-tert-butyl-1,8-diiodo-9H-carbazol-9-yl)acetonitrile, C22H24I2N2
  8. Crystal structure of 3-phenylpropyl 2-(6-methoxynaphthalen-2-yl)propanoate, C23H24O3
  9. The crystal structure of (4-fluorophenyl)(5-(hydroxymethyl)furan-2-yl)methanol, C12H11FO3
  10. Crystal structure of the dihydrate of tetraethylammonium 1,3,5-thiadiazole-5-amido-2-carbamate, C11H27N5O4S
  11. Crystal structure of (Z)-4-[(p-tolylamino)(furan-2-yl)methylene]-3-phenyl-1-1-p-tolyl-1H-phenyl-1H-pyrazol-5(4H)-one, C28H23N3O2
  12. The crystal structure of (E)-3-(2-chlorophenyl)-1-ferrocenylprop-2-en-1-one, C19H15ClFeO
  13. The pseudosymmetric crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium hexachloridostannate(IV), C10H16N2SnCl6
  14. Crystal structure of (2-(1-hydroxyheptyl)octahydro-8aH-chromene-5,8,8a-triol), C16H30O5
  15. The crystal structure of N-cyclohexyl-3-hydroxy-4-methoxybenzamide, C14H19NO3
  16. Crystal structure of 1-(4-hydroxybenzyl)-4-methoxy-9,10-dihydrophenanthrene-2,7-diol from Arundina graminifolia, C22H20O4
  17. The crystal structure of N-cyclopentyl-3-hydroxy-4-methoxybenzamide, C13H17NO3
  18. The crystal structure of 2,5,5-triphenyl-3,5-dihydro-4H-imidazol-4-one, C21H16N2O
  19. Crystal structure of 1H-1,2,3-Triazolo[4,5-b]-pyridin-4-ium nitrate, C5H5N5O3
  20. Crystal structure of (Z)-4-(((4-bromophenyl)amino)(furan-2-yl)methylene)-2,5-diphenyl-2,4-dihydro-3H-pyrazol-3-one, C26H18BrN3O2
  21. Crystal structure of 2-(4-methoxyphenyl)-3-methyl-1,8-naphthyridine, C16H14N2O
  22. The crystal structure of 3-([1,1′-biphenyl]-2-yl)-1,2-diphenylbenzo[b]phosphole-1-oxide, C32H23OP
  23. The crystal structure of ammonium (E)-4-((4-carboxyphenyl)diazenyl)benzoate, C14H13N3O4
  24. Crystal structure of bis(5-amino-1,2,4-triazol-4-ium-3-yl)methane sulfate, C5H10N8O4S
  25. The crystal structure of phenantroline-κ2 N,N′-bis(6-phenylpyridine-2-carboxylato-κ2 N,O)copper(II), C36H24N4O4Cu
  26. The crystal structure of tris(6-methylpyridin-2-yl)phosphine oxide, C18H18N3OP
  27. The crystal structure of N-(2′-hydroxymethyl-5′-phenyl-3′,4′-dihydro-[1,1′:3′,1″-terphenyl]- 1′(2′H)-yl)-P,P-diphenylphosphinic amide, C37H34NO2P
  28. Crystal structure of (E)-4-(6-(4-(2-(pyridin-4-yl)vinyl)phenoxy)pyrimidin-4-yl)morpholine, C21H20N4O2
  29. Crystal structure of 5-(adamantan-1-yl)-3-[(4-trifluoromethylanilino)methyl]-2,3-dihydro-1,3,4-oxadiazole-2-thione, C20H22F3N3OS
  30. Crystal structure of 2,2-dichloro-1-(4-chloro-1H-indol-1-yl)ethan-1-one, C10H6Cl3NO
  31. The crystal structure of 4-(((3-bromo-5-(trifluoromethyl)pyridin-2-yl)oxy)methyl)benzonitrile, C28H16Br2F6N4O2
  32. The crystal structure of 1H-benzimidazole-2-carboxamide, C8H7N3O
  33. The crystal structure of Histidinium hydrogensquarate, C10H11N3O6
  34. The crystal structure of 3-amino-5-carboxypyridin-1-ium iodide, C6H7IN2O2
  35. Crystal structure of (E)-amino(2-(3-ethoxy-4-hydroxybenzylidene)hydrazineyl)methaniminium nitrate hemihydrate C10H16N5O5.5
  36. Crystal structure of 1,2-bis(4,5-dinitro-1H-imidazol-1-yl)ethane, C8H6N8O8
  37. The crystal structure of diaqua-bis(pyrazolo[1,5-a]pyrimidine-3-carboxylato-κ2N,O)manganese(II), C14H12N6O6Mn
  38. The crystal structure of catena-poly[aqua-2,2′bipyridine-κ2N,N′-(μ2-5-ethoxyisophthalato-κ 4O,O′:Oʺ,O′ʺ)cadmium(II)] monohydrate, C20H20CdN2O7
  39. The crystal structure of (1S,3R)-1-(4-isopropylphenyl)-3-(methoxycarbonyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-iumchloride monohydrate, C22H27ClN2O3
  40. Crystal structure of 1-isopropyl-3-(prop-1-en-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, C11H15N5
  41. The crystal structure of (2,2′-bipyridine-κ2N,N′)- bis(6-phenylpyridine-2-carboxylate-κ2N,O)manganese(II)] monohydrate, C34H26N4O5Mn
  42. Crystal structure of the cocrystal 1,3,5,7-tetranitro-1,3,5,7-tetrazoctane ─ 2,3-dihydroindole (1/1), C12H17N9O8
  43. Crystal structure of 3-acetyl-6-hydroxy-2H-chromen-2-one monohydrate, C11H10O5
  44. Crystal structure of 6,9-diamino-2-ethoxyacridinium 3,5-dinitrobenozate — dimethylsulfoxide — water (1/1/1), C24H27N5O9S
  45. The crystal structure of 4,4′-bipyridinium bis-(2-hydroxy-3-methoxybenzoate), 2(C8H7.68O4)·C10H8.64N2
  46. Crystal structure of (Z)-4-(((4-fluorophenyl)amino)(furan-2-yl)methylene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one
  47. The crystal structure of bis(4-chloro-2-(((2-chloroethyl)imino)methyl)phenolato-κ2N,O)-oxidovanadium(IV), C18H16Cl4N2O3V
  48. The crystal structure of 17-(bromoethynyl)-17-hydroxy-10, 13-dimethyl- 1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one, C21H27BrO2
  49. The crystal structure of 4-((6-fluoropyridin-2-yloxy)methyl)benzonitrile, C13H9FN2O
  50. Crystal structure of (Z)-2-(1-bromo-2-phenylvinyl)-5-ethyl-2-methyl-1,3-dioxane-5-carboxylic acid, C15H17Br1O4
  51. Crystal structure of catena-poly[tribenzyl-κ1C-(μ2-6-oxidopyridin-1-ium-3-carboxylato-κ2O:O’)tin(IV)-dichloromethane-methanol (1/1/1), C29H31Cl2NO4Sn
  52. Crystal structure of bis{2-(tert-butyl)-6-((E)-((4-((E)-1-(methoxyimino)ethyl)phenyl)imino)methyl)phenolato-κ2N,O}zinc(II), C40H46N4O4Zn
  53. Crystal structure of diaqua-bis(μ2-2-carboxy-3,4,5,6-tetrafluorobenzoato-κ2O:O′)-bis(phenanthroline-κ2N,N′)-bis(μ2-3,4,5,6-tetrafluorophthalato-κ3O:O,O′)dieuropium(III) – phenanthroline (1/2), C40H19EuF8N4O9
  54. The crystal structure of diaqua-bis(6-phenylpyridine-2-carboxylato-κ2N,O) manganese(II) — water — dimethylformamide (1/2/1), C27H31N3O9Mn
  55. The crystal structure of bis(pyrazolo[1,5-a]pyrimidine-3-carboxylato-κ2N,O)-copper(ii), C14H8N6O4Cu
  56. Crystal structure of poly[(μ2-1-(1-imidazolyl)-4-(imidazol-1-ylmethyl)benzene-κ2N:N′)-(μ3-pyridazine-4,5-dicarboxylate-κ3O:O′:N)]copper(II) hydrate, C19H16CuN6O5
  57. Crystal structure of acrinidinium tetrafluorohydrogenphthalate, C21H11F4NO4
  58. Crystal structure of 2-(1H-pyrazol-3-yl-κN)pyridine-κN-bis(2-(2,4-difluorophenyl)pyridinato-κ2C,N)iridium(III) sesquihydrate, C30H18F4IrN5·1.5[H2O]
  59. Crystal structure of 2-(2-hydroxy-5-nitrophenyl)-5-methyl-1,3-dioxane-5-carboxylic acid, C12H13N1O7
  60. The crystal structure of 1,2-bis(pyridinium-4-yl)ethane diperchlorate, C12H14N2·2ClO4 – a second polymorph
  61. The crystal structure of [(1,10-phenantroline-κ2N,N′)-bis(6-phenylpyridine-2-carboxylato-κ2N,O)manganese(II)] monohydrate, C36H26N4O5Mn
  62. Crystal structure of 1,2-bis(2,2,3,3,5,5,5-heptamethyl-1,1,4,4- tetrakis(trimethylsilyl)pentasilan-1-yl)ditellane, C38H114Si18Te2
  63. Crystal structure of 1,2-bis(2,4-dinitro-1H-imidazol-1-yl)ethane – dimethylformamide (1/1), C11H13N9O9
  64. Crystal structure of (Z)-3-((tert-butylamino) methylene)-2-(2-hydroxynaphthalen-1-yl) chroman-4-one, C24H23NO3
  65. Synthesis and crystal structure of (E)-1-(4-(((E)-3-(tert-butyl)-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-ethyl oxime, C21H26N2O2
  66. Crystal structure of the double salt bis(5-amino-1,2,4-triazol-4-ium-3-yl)methane hydrogen oxalate hemioxalate, C8H11N8O6
  67. Hydrothermal synthesis and crystal structure of catena-poly[diaqua-bis(μ2-4-[(4-pyridinylmethyl)amino]benzoato-κ2N:O)cobalt(II)]–1,2bi(4-pyridyl)ethene–water (1/1/1), C50H50N8O8Co
  68. Crystal structure of 3-(3-bromophenyl)-1′,3′-dimethyl-2′H,3H,4H-spiro[furo[3, 2-c]chromene-2,5′-pyrimidine]-2′,4,4′,6′(1′H,3′H) tetraone, C22H15BrN2O6
  69. The crystal structure of poly[aqua-(μ2-4,4′- bis(imidazolyl)biphenyl-κ2N:N′)-(μ2-3-nitrobenzene-1,2-dicarboxylato-κ2O:O′)]copper (II) hydrate, C26H21N5O8Cu
  70. The crystal structure of bis(4-(6-carboxy-8-ethyl-3-fluoro-5-oxo-5,8-dihydro-1,8-naphthyridin-2- yl)piperazin-1-ium) adipate tetrahydrate, C36H52F2N8O14
  71. Synthesis and crystal structure of poly[aqua(μ4-(1R,2S,4R)-4-hydroxy-1-((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)pyrrolidin-1-ium-2-carboxylate-κ4O:O′:O″:O‴)sodium(I)] monohydrate, C21H22NNaO12S
  72. Crystal structure of chlorido-(η6-toluene)(2,2′-bipyridine-κ2N,N′)ruthenium(II) hexafluorophosphate, C17H16ClN2RuPF6
  73. The crystal structure of (R)-6-hydroxy-8-methoxy-3-methylisochroman-1-one, C11H12O4
  74. Crystal structure of catena-poly[(5,5,7,12,12,14-hexamethyl -1,4,8,11-tetraazacyclotetradecane- κ4N,N′,Nʺ,N‴)nickel(II)-(μ2-perchlorato-κ2O:O′)] 3,5-dicarboxybenzoate – methanol (1/2), C27H49ClN4NiO12
  75. The crystal structure of 4-(chloromethyl)benzonitrile, C8H6ClN
  76. The crystal structure of dimethylammonium 8-[(7,9-dioxo-6,10-dioxaspiro[4.5]decan-8-ylidene)methyl]-9-oxo-6,10-dioxaspiro[4.5]dec-7-en-7-olate, C19H25NO8
  77. Crystal structure of (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-((1-acetyl-5-bromo-4-chloro-1H-indol-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate hemihydrate C24H25BrClNO11
  78. The crystal structure of the co-crystal tetrakis[2-(tris(4-methoxyphenyl)stannyl)ethyl]silane – tetrahydrofuran – toluene – tetrahydrofurane (1/1/1), C103H116O13SiSn4
  79. Crystal structure of methyl 3-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)propanoate, C16H13NO4
  80. Crystal structure of ethyl (Z)-3-amino-2-cyano-3-(2-oxo-2H-chromen-3-yl)acrylate, C15H12N2O4
  81. Crystal structure of methyl 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetate, C15H11NO4
  82. Crystal structure of catena-poly[diaqua-bis(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)cobalt(II)] tetrafluoroterephthalate, C26H28N8O6F4Co
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 6.9.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2022-0081/html
Scroll to top button