Home Crystal structure of (3,6-di(2-pyridyl)-4-methylphenyl pyridazine-k 2 N,N′)-bis(1-phenyl-pyrazole-κ 2 C,N) iridium(III) hexafluorophosphate, C39H29F6IrN8P
Article Open Access

Crystal structure of (3,6-di(2-pyridyl)-4-methylphenyl pyridazine-k 2 N,N′)-bis(1-phenyl-pyrazole-κ 2 C,N) iridium(III) hexafluorophosphate, C39H29F6IrN8P

  • Jun Qian ORCID logo EMAIL logo , Liang Ma and Yida Wang
Published/Copyright: July 23, 2024
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 239 Issue 5

Abstract

C39H29F6IrN8P, orthorhombic, Pbca (no. 61), a = 19.6205(7) Å, b = 16.2026(6) Å, c = 23.0700(8) Å, V = 7334.0(5) Å3, Z = 8, R gt (F) = 0.0258, wR ref (F 2) = 0.0611, T = 293 K.

CCDC no.: 2369932

The molecular structure is shown in the figure. 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: Red block
Size: 0.23 × 0.20 × 0.18 mm
Wavelength:

μ:		 Mo Kα radiation (0.71073 Å)

3.76 mm−1
Diffractometer, scan mode:

θ max, completeness:		 Bruker APEX-II, φ and ω

26.4°, >99 %
N(hkl)measured, N(hkl)unique, R int: 23365, 7498, 0.017
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 6340
N(param)refined: 497
Programs: Bruker, 1 Olex2, 2 SHELX, 3 , 4 PLATON 5
Table 2:

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

Atom x y z U iso*/U eq
Ir1 0.37036 (2) 0.60189 (2) 0.29156 (2) 0.01751 (5)
N1 0.22406 (19) 0.4377 (2) 0.47339 (15) 0.0435 (9)
N2 0.26147 (13) 0.55758 (16) 0.38027 (11) 0.0206 (6)
N3 0.29082 (14) 0.62067 (17) 0.35161 (11) 0.0200 (6)
N4 0.36202 (13) 0.73302 (16) 0.29553 (11) 0.0192 (5)
N5 0.30704 (15) 0.59503 (18) 0.22326 (12) 0.0246 (6)
N6 0.29107 (15) 0.51631 (18) 0.20603 (12) 0.0264 (6)
N7 0.44084 (14) 0.59431 (17) 0.35469 (12) 0.0233 (6)
N8 0.50615 (14) 0.58543 (17) 0.33565 (13) 0.0240 (6)
C1 0.45581 (18) 0.5980 (2) 0.24255 (15) 0.0240 (7)
C2 0.4635 (2) 0.6041 (2) 0.18230 (16) 0.0327 (8)
H2 0.4249 0.6078 0.1590 0.039*
C3 0.5277 (2) 0.6047 (2) 0.15656 (18) 0.0380 (9)
C4 0.5854 (2) 0.5995 (2) 0.19105 (19) 0.0390 (10)
H4 0.6282 0.6005 0.1737 0.047*
C5 0.58060 (19) 0.5929 (2) 0.25060 (18) 0.0315 (8)
H5 0.6193 0.5894 0.2738 0.038*
C6 0.51565 (18) 0.5917 (2) 0.27446 (15) 0.0242 (7)
C7 0.54802 (19) 0.5704 (2) 0.38079 (17) 0.0322 (8)
H7 0.5948 0.5618 0.3788 0.039*
C8 0.5093 (2) 0.5699 (2) 0.42982 (16) 0.0332 (8)
H8 0.5246 0.5613 0.4675 0.040*
C9 0.44248 (19) 0.5849 (2) 0.41237 (15) 0.0275 (8)
H9 0.4049 0.5878 0.4369 0.033*
C10 0.36508 (17) 0.4778 (2) 0.28343 (14) 0.0236 (7)
C11 0.3988 (2) 0.4151 (2) 0.31383 (17) 0.0307 (8)
H11 0.4273 0.4292 0.3445 0.037*
C12 0.3907 (2) 0.3326 (2) 0.29943 (19) 0.0395 (10)
H12 0.4145 0.2923 0.3198 0.047*
C13 0.3470 (2) 0.3097 (2) 0.2545 (2) 0.0419 (10)
H13 0.3410 0.2541 0.2456 0.050*
C14 0.3124 (2) 0.3691 (2) 0.22313 (18) 0.0373 (9)
H14 0.2832 0.3546 0.1930 0.045*
C15 0.32264 (18) 0.4514 (2) 0.23812 (15) 0.0267 (7)
C16 0.2519 (2) 0.5182 (3) 0.15780 (16) 0.0347 (9)
H16 0.2348 0.4729 0.1378 0.042*
C17 0.2422 (2) 0.5992 (3) 0.14404 (16) 0.0367 (9)
H17 0.2171 0.6196 0.1130 0.044*
C18 0.27700 (19) 0.6453 (2) 0.18531 (15) 0.0295 (8)
H18 0.2790 0.7026 0.1863 0.035*
C19 0.39876 (18) 0.7875 (2) 0.26440 (14) 0.0232 (7)
H19 0.4329 0.7677 0.2401 0.028*
C20 0.38781 (19) 0.8713 (2) 0.26708 (15) 0.0274 (7)
H20 0.4145 0.9073 0.2453 0.033*
C21 0.33658 (19) 0.9014 (2) 0.30254 (16) 0.0291 (8)
H21 0.3283 0.9579 0.3050 0.035*
C22 0.29799 (19) 0.8463 (2) 0.33416 (16) 0.0272 (7)
H22 0.2629 0.8653 0.3577 0.033*
C23 0.31181 (17) 0.7628 (2) 0.33061 (14) 0.0215 (7)
C24 0.27447 (16) 0.6995 (2) 0.36371 (14) 0.0208 (6)
C25 0.22658 (17) 0.7179 (2) 0.40680 (15) 0.0243 (7)
H25 0.2147 0.7724 0.4142 0.029*
C26 0.19725 (16) 0.6554 (2) 0.43806 (13) 0.0209 (7)
C27 0.21670 (16) 0.5739 (2) 0.42189 (13) 0.0202 (6)
C28 0.18467 (17) 0.4999 (2) 0.44863 (14) 0.0232 (7)
C29 0.11687 (15) 0.49932 (19) 0.44710 (14) 0.0189 (6)
H29 0.0927 0.5421 0.4298 0.023*
C30 0.0848 (2) 0.4357 (3) 0.47106 (19) 0.0405 (10)
H30 0.0375 0.4342 0.4696 0.049*
C31 0.1190 (2) 0.3709 (3) 0.49843 (19) 0.0431 (10)
H31 0.0950 0.3281 0.5159 0.052*
C32 0.1889 (2) 0.3720 (2) 0.49881 (17) 0.0370 (9)
H32 0.2129 0.3290 0.5160 0.044*
C33 0.14951 (17) 0.6708 (2) 0.48611 (15) 0.0250 (7)
C34 0.1577 (2) 0.6310 (3) 0.53894 (16) 0.0351 (9)
H34 0.1948 0.5962 0.5447 0.042*
C35 0.1113 (2) 0.6428 (3) 0.58280 (16) 0.0387 (9)
H35 0.1176 0.6157 0.6180 0.046*
C36 0.0554 (2) 0.6939 (2) 0.57585 (17) 0.0368 (9)
C37 0.0474 (2) 0.7342 (2) 0.52331 (18) 0.0365 (9)
H37 0.0101 0.7688 0.5178 0.044*
C38 0.09407 (19) 0.7240 (2) 0.47878 (16) 0.0303 (8)
H38 0.0885 0.7524 0.4441 0.036*
C39 0.0046 (2) 0.7035 (3) 0.6244 (2) 0.0517 (12)
H39A −0.0355 0.7306 0.6101 0.078*
H39B 0.0243 0.7360 0.6549 0.078*
H39C −0.0074 0.6501 0.6392 0.078*
P1 0.37136 (5) 0.64473 (6) 0.57764 (4) 0.0311 (2)
F1 0.34213 (15) 0.55658 (15) 0.55790 (11) 0.0517 (7)
F2 0.39947 (16) 0.73218 (15) 0.59746 (12) 0.0567 (7)
F3 0.39538 (18) 0.60476 (16) 0.63710 (10) 0.0628 (8)
F4 0.34645 (17) 0.68291 (16) 0.51755 (12) 0.0610 (8)
F5 0.44202 (14) 0.62210 (18) 0.54876 (12) 0.0574 (7)
F6 0.29975 (15) 0.66653 (18) 0.60624 (15) 0.0703 (9)

1 Source of materials

All the reagents were A. R. grade commercially available and used as received without any further purification. The cyclometalated chloro-bridged iridium(III) dimer, [(ppya)2Ir(μ–Cl)]2 (ppya = 1-phenyl-pyrazole), was synthesized following the reported literature procedures 6 by heating IrCl3 · 3H2O (1 equiv) and 1-phenyl-pyrazole (2.5 equiv) in a mixed solution of water and ethylene glycol ether (v/v = 1/4) at 135 ∘C under the nitrogen atmosphere. Tetrazine (1 equiv) and 4-ethynyl toluene (1 equiv) were added into toluene with strong stirring at 140 ∘C to obtain 3,6-di(2-pyridyl)-4-methylphenyl pyridazine (DpTz–MPh) after 144 h. The iridium(III) dimer [(ppya)2Ir(μ–Cl)]2 (1 equiv) and DpTz–MPh ligand (1 equiv), as well as potassium hexafluorophosphate (1 equiv) were added together in a mixed solvent containing dichloromethane and methanol (v/v = 2/1). The mixture was heated to 85 ∘C, then refluxed in a dark N2 atmosphere for 24 h to obtain reddish solid products. The obtained solid product (137.5143 mg, 0.1446 mmol) was dissolved in dichloromethane (1 mL), after filtration, 0.5 mL of buffer layer (Vdichloromethane/Vn-hexane = 1/1) was added, and finally 3 mL of n-hexane was added. Red block crystals were obtained after 11 days at room temperature in dark with a yield of 73.91 mg (54 % based Ir). Anal. Calcd. for C39H29F6IrN8P: C, 49.41 %; H, 3.19 %; N, 11.82 %. Found C, 49.23 %; H, 3.34 %; N, 11.71 %. IR (KBr, ν/cm−1): 3434(m), 3048(s), 1580(s), 1479(m), 1395(vs), 1020(m)(pyridine: C=N), 985(m), 795(m).

2 Experimental details

The crystal structure determination was carried on a Bruker APEX-II diffractometer. The structure was solved by Direct Methods and refined using the SHELX software. 3 All of the hydrogen atoms were added by theoretical method and isotropic displacement parameters were given (U iso = 1.2 (1.5 for methyl hydrogen) U eq, U eq is the equivalent isotropic displacement parameter of the parent atom). 5

3 Comment

Under the impetus of potential applications as functional materials, such as organic light-emitting diodes (OLEDs), light-emitting electro-chemical cells (LECs), biosensing, photocatalysis, and nonlinear optics, cyclometalated iridium(III) complexes have received enormous interests. 6 , 7 , 8 As a result, considerable efforts in crystal engineering have been devoted to the design and synthesis of various kinds of cyclometalated iridium(III) complexes with diverse physical functions. 9 , 10 Up to now, several synthetic strategies have been successfully applied in the construction of cyclometalated iridium(III) complexes. 11 , 12 Among these, the construction of cyclometalated iridium(III) complexes based on versatile iridium(III) dimers has been regarded as an applicable approach. 13 In addition, the modification of structures via the auxiliary N,Nʹ ligands helps to elaborate the influences of electron effects on the photophysical properties of the corresponding cyclometalated iridium(III) complexes. 14 , 15

The asymmetric unit of the title structure consists of one Ir3+ cation, one DpTz-MPh ligand, two ppya ligands, and one PF− 6 anion (see the Figure). The Ir(III) center is 6-coordinated by four N atoms and two C atoms from both pyrazole and pyridine rings, forming an octahedral spatial configuration. Two chelated ppya ligands are arranged perpendicular to each other with two N atoms residing in trans positions, whereas the cyclometalated carbon atoms are in cis positions. The Ir–C bond length is 2.023(3) Å, while the distances of Ir–N range from 2.010(3) Å to 2.133(3) Å, which are comparable with similar structures. 16 The adjacent metal-organic structural units can be further extended into a three-dimensional supramolecular structure by hydrogen bonding, where the hydrogen bonds are formed by the H atoms on the chelated ligand ppya and auxiliary ligand DpTz–MPh with the F atoms of the PF− 6 anion.

Corresponding author: Jun Qian, School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, Jiangsu 212013, P.R. China, E-mail:

  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 funded by National Natural Science Foundation of China (grant No. 51602130).

  3. Competing interests: The authors declare no conflicts of interest regarding this article.

References

1. BRUKER. Saint, Apex2 and Sadabs; Bruker AXS Inc.: Madison, Wisconsin, USA, 2009.Search in Google Scholar

2. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A.; 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. Shelxt-Integrated Space-Group and Crystal-Structure Determination. Acta Crystallogr. 2015, A71, 3–8; https://doi.org/10.1107/s2053273314026370.Search in Google Scholar

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

6. Kwon, T. H.; Cho, H. S.; Kim, M. K.; Kim, J. W.; Kim, J. J.; Lee, K. H.; Park, S. J.; Shin, I. S.; Kim, H.; Shin, D. M.; Chung, Y. K.; Hong, J. I. Color Tuning of Cyclometalated Iridium Complexes through Modification of Phenylpyrazole Derivatives and Ancillary Ligand Based on Ab Initio Calculations. Organometallics 2005, 24, 1578–1585; https://doi.org/10.1021/om049419e.Search in Google Scholar

7. Liu, J. L.; Liu, Y.; Liu, Q.; Li, C. Y.; Sun, L. N.; Li, F. Y. Iridium(III) Complex-Coated Nanosystem for Ratiometric Upconversion Luminescence Bioimaging of Cyanide Anions. J. Am. Chem. Soc. 2011, 133, 15276–15279; https://doi.org/10.1021/ja205907y.Search in Google Scholar PubMed

8. Sun, W. F.; Pei, C.; Lu, T.; Cui, P.; Li, Z.; McCleese, C.; Fang, Y.; Kilina, S.; Song, Y.; Burda, C. Reverse Saturable Absorbing Cationic Iridium(III) Complexes Bearing the 2-(2-quinolinyl)quinoxaline Ligand: Effects of Different Cyclometalating Ligands on Linear and Nonlinear Absorption. J. Mater. Chem. C 2016, 4, 5059–5072; https://doi.org/10.1039/c6tc00710d.Search in Google Scholar

9. Fan, C.; Zhu, L.; Jiang, B.; Li, Y.; Zhao, F.; Ma, D.; Qin, J.; Yang, C. J. High Power Efficiency Yellow Phosphorescent Oleds by Using New Iridium Complexes with Halogen-Substituted 2-phenylbenzo[d]thiazole Ligands. Phys. Chem. C 2013, 117, 19134–19141; https://doi.org/10.1021/jp406220c.Search in Google Scholar

10. Lee, S.; Kim, S. O.; Shin, H.; Yun, H. J.; Yang, K.; Kwon, S. K.; Kim, J. J.; Kim, Y. H. Deep-blue Phosphorescence from Perfluoro Carbonyl-Substituted Iridium Complexes. J. Am. Chem. Soc. 2013, 135, 14321–14328; https://doi.org/10.1021/ja4065188.Search in Google Scholar PubMed

11. Costa, R. D.; Monti, F.; Accorsi, G.; Barbieri, A.; Bolink, H. J.; Orti, E.; Armaroli, N. Photophysical Properties of Charged Cyclometalated Ir(III) Complexes: A Joint Theoretical and Experimental Study. Inorg. Chem. 2011, 50, 7229–7238; https://doi.org/10.1021/ic200820t.Search in Google Scholar PubMed

12. Skorka, L.; Filapek, M.; Zur, L.; Malecki, J. G.; Pisarski, W.; Olejnik, M.; Danikiewicz, W.; Krompiec, S. Highly Phosphorescent Cyclometalated Iridium(III) Complexes for Optoelectronic Applications: Fine Tuning of the Emission Wavelength through Ancillary Ligands. J. Phys. Chem. C 2016, 120, 7284–7294; https://doi.org/10.1021/acs.jpcc.6b01663.Search in Google Scholar

13. Liu, B. Q.; Lystrom, L.; Brown, S. L.; Hobbie, E. K.; Kilina, S.; Sun, W. F. Impact of Benzannulation Site at the Diimine (NN̂) Ligand on the Excited-State Properties and Reverse Saturable Absorption of Biscyclometalated Iridium(III) Complexes. Inorg. Chem. 2019, 58, 5483–5493; https://doi.org/10.1021/acs.inorgchem.8b03162.Search in Google Scholar PubMed

14. Sarma, M.; Chatterjee, T.; Bodapati, R.; Krishnakanth, K. N.; Hamad, S.; Rao, V.; Das, S. K. Cyclometalated Iridium(III) Complexes Containing κ24,4′-π-conjugated κ22,2′-bipyridine Derivatives as the Ancillary Ligands: Synthesis, Photophysics, and Computational Studies. Inorg. Chem. 2016, 55, 3530–3540; https://doi.org/10.1021/acs.inorgchem.5b02999.Search in Google Scholar PubMed

15. Zaarour, M.; Singh, A.; Latouche, C.; Williams, J. A. G.; Ledoux-Rak, I.; Zyss, J.; Boucekkine, A.; Bozec, H. L.; Guerchais, V.; Dragonetti, C.; Colombo, A.; Roberto, D.; Valore, A. Linear and Nonlinear Optical Properties of Tris-Cyclometalated Phenylpyridine Ir(III) Complexes Incorporating π-conjugated Substituents. Inorg. Chem. 2013, 52, 7987–7994; https://doi.org/10.1021/ic400541e.Search in Google Scholar PubMed

16. Qian, J.; Chen, C. J.; Ma, L. Wang, Y. D. Crystal Structure of (2-phenylimino methylquinoline-κ2N,N′)-bis(1-phenylpyrazole-κ2C,N′)-Iridium(III) Hexafluorophosphate, C34H26F6IrN6P. Z. Kristallogr. N. Cryst. Struct. 2023, 238, 1165–1167; https://doi.org/10.1515/ncrs-2023-0375.Search in Google Scholar
Received: 2024-06-08
Accepted: 2024-07-12
Published Online: 2024-07-23
Published in Print: 2024-10-28

© 2024 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

Articles in the same Issue

  1. Frontmatter
  2. Editorial
  3. Editorial 2024 – New developments and changes of Zeitschrift für Kristallographie – New Crystal Structures
  4. New Crystal Structures
  5. Hydrogen bonding and π⋅⋅⋅halogen interactions in the crystal structure of bis(theophyllinium) hexachloridoplatinate(IV) monohydrate
  6. The crystal structure of 6-amino-2-carboxypyridin-1-ium perchlorate, C6H7ClN2O6
  7. Crystal structure of poly[(μ4-(3-amino-1H-1,2,4-triazol-1-yl)benzene-1,3-dicarboxylato-κ 4 N:O:O':O')(1-methylpyrroldin-2-one-κ1O)dicopper(II)] – 1-methylpyrroldin-2-one (1/3), C40H48Cu2N12O12
  8. The crystal structure of 18-crown-6-k6O6(2,4,5-trinitroimidazol-1-ido-k1O)potassium(I)
  9. Crystal structure of poly[tetraaqua-bis(μ2-5-bromoisophthalato-κ3O,O′:O″)-(μ2-1,5-bis(imidazol-2-methyl)pentane-κ2N:N′)dicadmium(II)] dihydrate
  10. Crystal structure of (5R,6S,E)-5-acetoxy-2-methyl-6-((2aR,3R,5aS,5bS,11aR,12aS)-2a,5a,8,8-tetramethyl-9-oxotetradecahydro-1H,12H-cyclopenta[a]cyclopropa[e]phenanthren-3-yl)hept-2-enoic acid, C32H48O5
  11. The crystal structure of poly[diaqua-bis(μ2 -thiocyanato-κ2N:O)cobalt(II) monohydrate
  12. The crystal structure of 1,3,5-tri(1H-imidazol-1-yl)benzene–2,3,5,6-tetrachlorobenzene-1,4-dicarboxylic acid (1/1)
  13. Crystal structure of dichlorido-bis(1-[(2-ethyl-benzimidazole-1-yl)methyl]-1H–benzotriazole) cadmium(II), C32H32CdN10OCl2
  14. The crystal structure of N′-(tert-butyl)-N′-(3,5-dimethylbenzoyl)-3-methoxy-N,2-dimethylbenzohydrazide, C23H30N2O3
  15. Crystal stucture of 3-benzamido-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluorobenzamide
  16. Crystal structure of bis(μ-benzeneselenolato)-(tetracarbonyl)-{μ-[N-(diphenylphosphanyl)-N-(3-ethynylphenyl)-P,P-diphenylphosphinous amide]} diiron, C48H35Fe2NO4P2Se2
  17. The crystal structure of 2′-(p-tolyl)-4′H-spiro[isochromane-1,1′-naphthalene]-3,4′-dione, C25H18O3
  18. The crystal structure of poly[hexaqua-tetrakis(μ4-pyridine-2,4-dicarboxylate-κ5N: O: O′: O″: O‴)-bi(μ2-pyridine-2,4-dicarboxylate-κ3N: O: O′)-digadolinium(III)tricopper (II)], [Gd2Cu3(C7H3NO4)6(H2O)6] n
  19. Crystal structure of poly[bis(4-(4-(pyridin-4-yl)phenyl)pyridin-1-ium-κ1N)-(μ4-benzene-1,2,4,5-tetracarboxylato-κ5O:O′: O″:O‴:O⁗)-(μ2-2,5-dicarboxyterephthalato-κ2O:O′)dizinc(II)], C52H32N4O16Zn2
  20. The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 2-carboxy-6-nitrobenzoate monohydrate, C24H25FN4O10
  21. Crystal structure of dichlorido-(1-((3,5-dimethyl-2,3-dihydro-1H-1,2,3-triazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-k1N)zinc(II), C22H24ZnN12Cl2
  22. The crystal structure of (3-chlorothiophene-2-carboxylato-κ2O, O′)-(2,2′-dipyridyl-κ2N,N′)lead(II), C20H12Cl2N2O4S2Pb
  23. Synthesis and crystal structure of (Z)-4-((1-(3-fluorophenyl)-1H-1,2,3-triazol-4-yl)methylene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, C19H14FN5O
  24. The crystal structure of the coordination compound catena-poly[(18-crown-6-ether-κ6O6)(4,5-dinitroimidazolato-κ1O)potassium(I)]
  25. Crystal structure of 7-(diethylamino)-3-(trifluoroacetyl)-2H-chromen-2-one, C15H14F3NO3
  26. Crystal structure of dichlorido-1-[(2-ethylimidazole-1-yl)methyl]-1H–benzotriazole κ1N zinc(II), C24H26ZnN10Cl2
  27. Crystal and molecular structure of 5-bromopyridine-2,3-diamine
  28. Crystal structure of catena-poly[bis(μ2-1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine-3-carboxylato-k3-O,O′:O″)hexaqua-dicobalt tetrahydrate], C26H36N4O20Co2
  29. Crystal structure of thiocyanate-κ1N-bis(μ1-2,6-diformyl-4-methylphenol oxime-κ2N,O)-manganese(III) acetonitrile solvate, C21H21MnN6O6S
  30. The crystal structure of pyrrolidin-1-yl pivalate, C9H13NO4
  31. The crystal structure of 2,2′-(2,2-diphenylethene-1,1-diyl)bis(1,4-dimethoxybenzene), C30H28O4
  32. Crystal structure of bis(benzyltrimethylammonium) tetrathiotungstate(VI), {(C6H5CH2)(CH3)3N}2[WS4]
  33. The crystal structure of ethyl (Z)-2-(ethoxymethylene)-3-oxobutanoate, C9H14O4
  34. The crystal structure of (E)-6-bromo-3,5-dimethyl-2-(1-phenylprop-1-en-2-yl)-3Himidazo[4,5b]pyridine, C17H16BrN3
  35. Crystal structure of (3S,3′S,4R,4′S)-3′-(furan-3-yl)-3-hydroxy-4′-methyl-3,5,6′,7′-tetrahydro-1H,3′H-4,5′-spirobi[isobenzofuran]-1,1′(4′H)-dione-methanol (1/1), C21H22O7
  36. Cocrystal structure of progesterone-isophthalic acid, C25H33O4
  37. The crystal structure of 3-(6-fluoro-1H-indol-3-yl)-1-methylquinoxalin-2(1H)-one, C17H12FN3O
  38. Crystal structure of S-(4-carboxybutyl)- l -cysteine
  39. The cocrystal of 2,2′-(hydrazine-1,1-diyl)bis(1H-imidazole-4,5-dicarbonitrile)– methanol (2/3)
  40. Crystal structure of (1′R,2′S,4′R,6′S)-4,6-dihydroxy-1′,8′,8′-trimethyl-3-(3-methylbutanoyl)-4′,8′,6′,1′,7,2′-hexahydro-1H-4′,6′-methanoxanthene-8-carbaldehyde, C23H30O5
  41. Crystal structure of (3,6-di(2-pyridyl)-4-methylphenyl pyridazine-k 2 N,N′)-bis(1-phenyl-pyrazole-κ 2 C,N) iridium(III) hexafluorophosphate, C39H29F6IrN8P
  42. Crystal structure of 1,5-bis[(E)-1-(2-hydroxyphenyl)ethylidene]thiocarbonohydrazide dimethyl sulfoxide monosolvate, C17H18N4O2S·C2H6OS
  43. Crystal structure of (S)-4-(2-(4-(2-acetyl-5-chlorophenyl)-3-methoxy-6-oxopyridazin-1(6H)-yl)-3-phenylpropanamido)benzoic acid monohydrate, C29H26ClN3O7
  44. The crystal structure of 1,3-bis(2,4-dinitro-1H-imidazol-1-yl)propane
  45. Crystal structure of 4-chlorobenzyl (S)-2-(6-methoxynaphthalen-2-yl)propanoate, C21H19ClO3
  46. Crystal structure of 1-(5-(benzo[d][1,3]dioxol-5-yl)-4-benzyl-1-(4-bromophenyl)-4,5-dihydro-1H-1,2,4-triazol-3-yl)ethan-1-one, C24H20BrN3O3
  47. The crystal structure of (Z)-3′-(2-(1-(3,4-dimethyl-phenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene)hydrazinyl)-2′-hydroxy-[1,1′-biphenyl]-3-carboxylicacid ─ methanol (1/1), C26H26N4O5
  48. Crystal structure of (S)-1-phenylpropan-1-aminium (S)-(1-phenylpropyl)carbamate C19H26N2O2
  49. Synthesis and crystal structure of methyl 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate, C18H16BrN3O2S
  50. The crystal structure of trichlorobis(pyridine-2,6-dithio-κS-carbomethylamido)antimony(III), [SbCl3(C9H11N3S2)2]
  51. Crystal structure of 1,8-dihydroxy-3-{[(triphenylstannyl)oxy]carbonyl} anthracene-9,10-dione, C33H22O6Sn
  52. The crystal structure of (E)-4-(2-(pyridin-4-ylmethylene)hydrazine-1-carbonyl)pyridin-1-ium-2-olate dihydrate, C12H14N4O4
  53. The crystal structure of 6-amino-pyridinium-2-carboxylate, C6H6N2O2
  54. The crystal structure of catena-poly[aqua-nitrato-κ3O,O:O′′-(1,10-phenanthroline-κ2N,N′)sodium(I)], C24H18N6O7Na2
  55. Retractions
  56. Retraction of: Crystal structure of bis[diaquaisonicotinatosamarium(III)]-µ-isonicotinato-[diisonicotinatocopper(II)], CuSm2(C6H4NO2)8(H2O)4
  57. Retraction of: Crystal structure of aqua(2,2′-bipyridine-k 2 N:N′)(nitrato)-(4-aminobenzoato)cadmium(II) nitrate, [Cd(H2O)(NO3)(C10H8N2)(C7H7NO2)][NO3]
https://doi.org/10.1515/ncrs-2024-0242
Creative Commons
BY 4.0

Articles in the same Issue

  1. Frontmatter
  2. Editorial
  3. Editorial 2024 – New developments and changes of Zeitschrift für Kristallographie – New Crystal Structures
  4. New Crystal Structures
  5. Hydrogen bonding and π⋅⋅⋅halogen interactions in the crystal structure of bis(theophyllinium) hexachloridoplatinate(IV) monohydrate
  6. The crystal structure of 6-amino-2-carboxypyridin-1-ium perchlorate, C6H7ClN2O6
  7. Crystal structure of poly[(μ4-(3-amino-1H-1,2,4-triazol-1-yl)benzene-1,3-dicarboxylato-κ 4 N:O:O':O')(1-methylpyrroldin-2-one-κ1O)dicopper(II)] – 1-methylpyrroldin-2-one (1/3), C40H48Cu2N12O12
  8. The crystal structure of 18-crown-6-k6O6(2,4,5-trinitroimidazol-1-ido-k1O)potassium(I)
  9. Crystal structure of poly[tetraaqua-bis(μ2-5-bromoisophthalato-κ3O,O′:O″)-(μ2-1,5-bis(imidazol-2-methyl)pentane-κ2N:N′)dicadmium(II)] dihydrate
  10. Crystal structure of (5R,6S,E)-5-acetoxy-2-methyl-6-((2aR,3R,5aS,5bS,11aR,12aS)-2a,5a,8,8-tetramethyl-9-oxotetradecahydro-1H,12H-cyclopenta[a]cyclopropa[e]phenanthren-3-yl)hept-2-enoic acid, C32H48O5
  11. The crystal structure of poly[diaqua-bis(μ2 -thiocyanato-κ2N:O)cobalt(II) monohydrate
  12. The crystal structure of 1,3,5-tri(1H-imidazol-1-yl)benzene–2,3,5,6-tetrachlorobenzene-1,4-dicarboxylic acid (1/1)
  13. Crystal structure of dichlorido-bis(1-[(2-ethyl-benzimidazole-1-yl)methyl]-1H–benzotriazole) cadmium(II), C32H32CdN10OCl2
  14. The crystal structure of N′-(tert-butyl)-N′-(3,5-dimethylbenzoyl)-3-methoxy-N,2-dimethylbenzohydrazide, C23H30N2O3
  15. Crystal stucture of 3-benzamido-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluorobenzamide
  16. Crystal structure of bis(μ-benzeneselenolato)-(tetracarbonyl)-{μ-[N-(diphenylphosphanyl)-N-(3-ethynylphenyl)-P,P-diphenylphosphinous amide]} diiron, C48H35Fe2NO4P2Se2
  17. The crystal structure of 2′-(p-tolyl)-4′H-spiro[isochromane-1,1′-naphthalene]-3,4′-dione, C25H18O3
  18. The crystal structure of poly[hexaqua-tetrakis(μ4-pyridine-2,4-dicarboxylate-κ5N: O: O′: O″: O‴)-bi(μ2-pyridine-2,4-dicarboxylate-κ3N: O: O′)-digadolinium(III)tricopper (II)], [Gd2Cu3(C7H3NO4)6(H2O)6] n
  19. Crystal structure of poly[bis(4-(4-(pyridin-4-yl)phenyl)pyridin-1-ium-κ1N)-(μ4-benzene-1,2,4,5-tetracarboxylato-κ5O:O′: O″:O‴:O⁗)-(μ2-2,5-dicarboxyterephthalato-κ2O:O′)dizinc(II)], C52H32N4O16Zn2
  20. The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 2-carboxy-6-nitrobenzoate monohydrate, C24H25FN4O10
  21. Crystal structure of dichlorido-(1-((3,5-dimethyl-2,3-dihydro-1H-1,2,3-triazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-k1N)zinc(II), C22H24ZnN12Cl2
  22. The crystal structure of (3-chlorothiophene-2-carboxylato-κ2O, O′)-(2,2′-dipyridyl-κ2N,N′)lead(II), C20H12Cl2N2O4S2Pb
  23. Synthesis and crystal structure of (Z)-4-((1-(3-fluorophenyl)-1H-1,2,3-triazol-4-yl)methylene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, C19H14FN5O
  24. The crystal structure of the coordination compound catena-poly[(18-crown-6-ether-κ6O6)(4,5-dinitroimidazolato-κ1O)potassium(I)]
  25. Crystal structure of 7-(diethylamino)-3-(trifluoroacetyl)-2H-chromen-2-one, C15H14F3NO3
  26. Crystal structure of dichlorido-1-[(2-ethylimidazole-1-yl)methyl]-1H–benzotriazole κ1N zinc(II), C24H26ZnN10Cl2
  27. Crystal and molecular structure of 5-bromopyridine-2,3-diamine
  28. Crystal structure of catena-poly[bis(μ2-1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine-3-carboxylato-k3-O,O′:O″)hexaqua-dicobalt tetrahydrate], C26H36N4O20Co2
  29. Crystal structure of thiocyanate-κ1N-bis(μ1-2,6-diformyl-4-methylphenol oxime-κ2N,O)-manganese(III) acetonitrile solvate, C21H21MnN6O6S
  30. The crystal structure of pyrrolidin-1-yl pivalate, C9H13NO4
  31. The crystal structure of 2,2′-(2,2-diphenylethene-1,1-diyl)bis(1,4-dimethoxybenzene), C30H28O4
  32. Crystal structure of bis(benzyltrimethylammonium) tetrathiotungstate(VI), {(C6H5CH2)(CH3)3N}2[WS4]
  33. The crystal structure of ethyl (Z)-2-(ethoxymethylene)-3-oxobutanoate, C9H14O4
  34. The crystal structure of (E)-6-bromo-3,5-dimethyl-2-(1-phenylprop-1-en-2-yl)-3Himidazo[4,5b]pyridine, C17H16BrN3
  35. Crystal structure of (3S,3′S,4R,4′S)-3′-(furan-3-yl)-3-hydroxy-4′-methyl-3,5,6′,7′-tetrahydro-1H,3′H-4,5′-spirobi[isobenzofuran]-1,1′(4′H)-dione-methanol (1/1), C21H22O7
  36. Cocrystal structure of progesterone-isophthalic acid, C25H33O4
  37. The crystal structure of 3-(6-fluoro-1H-indol-3-yl)-1-methylquinoxalin-2(1H)-one, C17H12FN3O
  38. Crystal structure of S-(4-carboxybutyl)- l -cysteine
  39. The cocrystal of 2,2′-(hydrazine-1,1-diyl)bis(1H-imidazole-4,5-dicarbonitrile)– methanol (2/3)
  40. Crystal structure of (1′R,2′S,4′R,6′S)-4,6-dihydroxy-1′,8′,8′-trimethyl-3-(3-methylbutanoyl)-4′,8′,6′,1′,7,2′-hexahydro-1H-4′,6′-methanoxanthene-8-carbaldehyde, C23H30O5
  41. Crystal structure of (3,6-di(2-pyridyl)-4-methylphenyl pyridazine-k 2 N,N′)-bis(1-phenyl-pyrazole-κ 2 C,N) iridium(III) hexafluorophosphate, C39H29F6IrN8P
  42. Crystal structure of 1,5-bis[(E)-1-(2-hydroxyphenyl)ethylidene]thiocarbonohydrazide dimethyl sulfoxide monosolvate, C17H18N4O2S·C2H6OS
  43. Crystal structure of (S)-4-(2-(4-(2-acetyl-5-chlorophenyl)-3-methoxy-6-oxopyridazin-1(6H)-yl)-3-phenylpropanamido)benzoic acid monohydrate, C29H26ClN3O7
  44. The crystal structure of 1,3-bis(2,4-dinitro-1H-imidazol-1-yl)propane
  45. Crystal structure of 4-chlorobenzyl (S)-2-(6-methoxynaphthalen-2-yl)propanoate, C21H19ClO3
  46. Crystal structure of 1-(5-(benzo[d][1,3]dioxol-5-yl)-4-benzyl-1-(4-bromophenyl)-4,5-dihydro-1H-1,2,4-triazol-3-yl)ethan-1-one, C24H20BrN3O3
  47. The crystal structure of (Z)-3′-(2-(1-(3,4-dimethyl-phenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene)hydrazinyl)-2′-hydroxy-[1,1′-biphenyl]-3-carboxylicacid ─ methanol (1/1), C26H26N4O5
  48. Crystal structure of (S)-1-phenylpropan-1-aminium (S)-(1-phenylpropyl)carbamate C19H26N2O2
  49. Synthesis and crystal structure of methyl 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate, C18H16BrN3O2S
  50. The crystal structure of trichlorobis(pyridine-2,6-dithio-κS-carbomethylamido)antimony(III), [SbCl3(C9H11N3S2)2]
  51. Crystal structure of 1,8-dihydroxy-3-{[(triphenylstannyl)oxy]carbonyl} anthracene-9,10-dione, C33H22O6Sn
  52. The crystal structure of (E)-4-(2-(pyridin-4-ylmethylene)hydrazine-1-carbonyl)pyridin-1-ium-2-olate dihydrate, C12H14N4O4
  53. The crystal structure of 6-amino-pyridinium-2-carboxylate, C6H6N2O2
  54. The crystal structure of catena-poly[aqua-nitrato-κ3O,O:O′′-(1,10-phenanthroline-κ2N,N′)sodium(I)], C24H18N6O7Na2
  55. Retractions
  56. Retraction of: Crystal structure of bis[diaquaisonicotinatosamarium(III)]-µ-isonicotinato-[diisonicotinatocopper(II)], CuSm2(C6H4NO2)8(H2O)4
  57. Retraction of: Crystal structure of aqua(2,2′-bipyridine-k 2 N:N′)(nitrato)-(4-aminobenzoato)cadmium(II) nitrate, [Cd(H2O)(NO3)(C10H8N2)(C7H7NO2)][NO3]
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 16.10.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2024-0242/html?srsltid=AfmBOoo-bqTMKFipaoiKcCBV0pKJH3iV5HP3EfOWApMXWDDBEcR_zd0c
Scroll to top button