Startseite The crystal structure of (Z)-3-(1-(2-((E)-4-isopropylbenzylidene)hydrazinyl)ethylidene) chroman-2,4-dione, C21H20N2O3
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The crystal structure of (Z)-3-(1-(2-((E)-4-isopropylbenzylidene)hydrazinyl)ethylidene) chroman-2,4-dione, C21H20N2O3

  • Vidoslav S. Dekić ORCID logo , Biljana R. Dekić ORCID logo , Dragana M. Sejmanović ORCID logo , Suzana Janićević ORCID logo , Biljana Krüger ORCID logo , Volker Kahlenberg ORCID logo und Marko V. Rodić ORCID logo EMAIL logo
Veröffentlicht/Copyright: 13. April 2023
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Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 238 Heft 3

Abstract

C21H20N2O3, monoclinic, P21/c (no. 14), a = 6.8892(3) Å, b = 21.8269(13) Å, c = 35.1144(19) Å, β = 90.344(5)°, V = 5280.1(5) Å3, Z = 12, R gt(F) = 0.0672, wR ref(F 2) = 0.1460, T = 170(2) K.

CCDC no.: 2246347

The molecular structure is shown in Figure (only molecule A, for the sake of clarity). 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: Yellow needle
Size: 0.65 × 0.15 × 0.07 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.09 mm−1
Diffractometer, scan mode: Gemini R ultra, ω
θ max, completeness: 26.4°, >99%
N(hkl) measured , N(hkl) unique, R int: 72,651, 10,810, 0.106
Criterion for I obs, N(hkl) gt: I obs > 2σ(I obs), 6256
N(param) refined: 713
Programs: CrysAlisPRO [1], SHELX [2, 3], PLATON [4]
Table 2:

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

Atom x y z U iso*/U eq
O1B 0.7604 (2) 0.83292 (8) 0.48987 (5) 0.0355 (5)
O2B 0.8508 (3) 0.89020 (9) 0.44210 (5) 0.0429 (5)
O3B 0.6501 (2) 0.98007 (8) 0.55870 (5) 0.0340 (4)
N1B 0.7455 (2) 1.05054 (10) 0.50521 (6) 0.0281 (5)
H1B 0.708429 1.043267 0.528722 0.034*
N2B 0.7698 (3) 1.11053 (10) 0.49373 (6) 0.0297 (5)
C2B 0.7909 (3) 0.89093 (12) 0.47467 (8) 0.0298 (6)
C3B 0.7499 (3) 0.94375 (12) 0.49802 (7) 0.0254 (6)
C4B 0.6868 (3) 0.93594 (12) 0.53669 (7) 0.0268 (6)
C5B 0.6021 (3) 0.86121 (13) 0.58802 (7) 0.0339 (7)
H5B 0.574727 0.894179 0.604812 0.041*
C6B 0.5808 (3) 0.80166 (14) 0.60024 (8) 0.0388 (7)
H6B 0.539948 0.793635 0.625552 0.047*
C7B 0.6187 (3) 0.75327 (14) 0.57566 (8) 0.0399 (7)
H7B 0.603406 0.712296 0.584257 0.048*
C8B 0.6784 (3) 0.76427 (13) 0.53897 (8) 0.0371 (7)
H8B 0.704267 0.731270 0.522102 0.045*
C9B 0.7757 (3) 1.00367 (12) 0.48222 (7) 0.0264 (6)
C10B 0.8325 (3) 1.01630 (12) 0.44214 (7) 0.0320 (6)
H10A 0.740637 0.996205 0.424764 0.048*
H10B 0.963421 1.000401 0.437670 0.048*
H10C 0.830798 1.060596 0.437604 0.048*
C11B 0.7267 (3) 1.15016 (12) 0.51923 (7) 0.0288 (6)
H11B 0.681768 1.136493 0.543310 0.035*
C12B 0.7448 (3) 1.21546 (12) 0.51221 (7) 0.0283 (6)
C13B 0.8227 (4) 1.23819 (13) 0.47845 (8) 0.0360 (7)
H13B 0.866905 1.210757 0.459369 0.043*
C14B 0.8354 (4) 1.30068 (13) 0.47285 (8) 0.0405 (7)
H14B 0.890314 1.315376 0.449841 0.049*
C15B 0.7712 (4) 1.34281 (13) 0.49950 (8) 0.0329 (6)
C16B 0.6921 (3) 1.31949 (13) 0.53283 (8) 0.0355 (7)
H16B 0.645426 1.347018 0.551621 0.043*
C17B 0.6798 (3) 1.25705 (13) 0.53923 (8) 0.0336 (6)
H17B 0.626363 1.242446 0.562389 0.040*
C18B 0.7793 (4) 1.41103 (14) 0.49190 (9) 0.0474 (8)
H18B 0.777501 1.432361 0.517099 0.057*
C19B 0.9630 (5) 1.43091 (16) 0.47136 (10) 0.0747 (11)
H19A 0.962933 1.413774 0.445563 0.112*
H19B 1.077000 1.416010 0.485375 0.112*
H19C 0.967150 1.475728 0.469926 0.112*
C20B 0.6001 (6) 1.43109 (17) 0.46993 (14) 0.1047 (17)
H20A 0.591799 1.408271 0.445942 0.157*
H20B 0.608372 1.475049 0.464495 0.157*
H20C 0.484175 1.422918 0.485164 0.157*
C4′B 0.6642 (3) 0.87325 (12) 0.55084 (7) 0.0251 (6)
C8′B 0.7001 (3) 0.82462 (12) 0.52706 (7) 0.0291 (6)
O1A 0.7185 (2) 0.66621 (8) 0.65816 (5) 0.0357 (5)
O2A 0.6670 (3) 0.60829 (9) 0.60852 (6) 0.0636 (7)
O3A 0.8480 (2) 0.52046 (8) 0.72678 (5) 0.0346 (5)
N1A 0.7797 (3) 0.44930 (9) 0.67178 (6) 0.0287 (5)
H1A 0.807467 0.456484 0.695866 0.034*
N2A 0.7724 (3) 0.38914 (10) 0.65924 (6) 0.0298 (5)
C2A 0.7114 (4) 0.60819 (12) 0.64176 (8) 0.0355 (7)
C3A 0.7564 (3) 0.55602 (11) 0.66533 (7) 0.0253 (6)
C4A 0.8065 (3) 0.56420 (12) 0.70488 (7) 0.0282 (6)
C5A 0.8557 (3) 0.63948 (13) 0.75760 (8) 0.0370 (7)
H5A 0.886239 0.606857 0.774514 0.044*
C6A 0.8577 (4) 0.69890 (14) 0.77065 (8) 0.0419 (7)
H6A 0.889291 0.707137 0.796518 0.050*
C7A 0.8136 (4) 0.74694 (14) 0.74608 (9) 0.0433 (8)
H7A 0.814818 0.787883 0.755258 0.052*
C8A 0.7684 (3) 0.73546 (13) 0.70857 (8) 0.0379 (7)
H8A 0.740004 0.768230 0.691619 0.045*
C9A 0.7464 (3) 0.49621 (12) 0.64896 (7) 0.0271 (6)
C10A 0.7007 (4) 0.48318 (12) 0.60807 (7) 0.0350 (7)
H10D 0.795222 0.504017 0.591838 0.052*
H10E 0.569900 0.498065 0.602023 0.052*
H10F 0.706995 0.438918 0.603568 0.052*
C11A 0.7604 (3) 0.34946 (12) 0.68602 (8) 0.0303 (6)
H11A 0.758399 0.363133 0.711702 0.036*
C12A 0.7499 (3) 0.28427 (12) 0.67825 (7) 0.0264 (6)
C13A 0.8072 (3) 0.25952 (12) 0.64342 (7) 0.0298 (6)
H13A 0.856849 0.285460 0.624060 0.036*
C14A 0.7915 (3) 0.19735 (12) 0.63717 (7) 0.0314 (6)
H14A 0.834721 0.181004 0.613622 0.038*
C15A 0.7143 (3) 0.15766 (12) 0.66429 (7) 0.0306 (6)
C16A 0.6562 (3) 0.18285 (13) 0.69880 (8) 0.0333 (6)
H16A 0.602842 0.157027 0.717831 0.040*
C17A 0.6749 (3) 0.24507 (12) 0.70580 (7) 0.0329 (6)
H17A 0.636141 0.261193 0.729701 0.039*
C18A 0.6848 (4) 0.09026 (13) 0.65621 (8) 0.0379 (7)
H18A 0.662517 0.069231 0.681108 0.045*
C19A 0.5023 (4) 0.08131 (14) 0.63164 (9) 0.0543 (9)
H19D 0.518009 0.102885 0.607374 0.081*
H19E 0.389378 0.097819 0.645041 0.081*
H19F 0.482699 0.037525 0.626787 0.081*
C20A 0.8595 (4) 0.06027 (14) 0.63762 (10) 0.0575 (9)
H20D 0.883605 0.079604 0.612912 0.086*
H20E 0.833721 0.016511 0.633906 0.086*
H20F 0.973804 0.065353 0.654072 0.086*
C4′A 0.8090 (3) 0.62678 (12) 0.71962 (7) 0.0278 (6)
C8′A 0.7648 (3) 0.67528 (13) 0.69585 (8) 0.0314 (6)
O1C 0.3170 (2) 0.33860 (8) 0.68020 (5) 0.0314 (4)
O2C 0.3648 (3) 0.39853 (9) 0.72891 (5) 0.0432 (5)
O3C 0.1730 (2) 0.47976 (8) 0.60917 (5) 0.0337 (4)
N1C 0.2424 (3) 0.55417 (10) 0.66221 (6) 0.0277 (5)
H1C 0.207394 0.545328 0.638706 0.033*
N2C 0.2527 (3) 0.61518 (10) 0.67301 (6) 0.0305 (5)
C2C 0.3197 (3) 0.39695 (12) 0.69559 (8) 0.0303 (6)
C3C 0.2732 (3) 0.44817 (12) 0.67110 (7) 0.0251 (6)
C4C 0.2199 (3) 0.43773 (12) 0.63185 (7) 0.0268 (6)
C5C 0.1736 (3) 0.35913 (13) 0.58059 (8) 0.0356 (7)
H5C 0.135217 0.390418 0.563313 0.043*
C6C 0.1805 (4) 0.29928 (13) 0.56856 (8) 0.0384 (7)
H6C 0.143977 0.289275 0.543186 0.046*
C7C 0.2408 (3) 0.25331 (13) 0.59334 (8) 0.0373 (7)
H7C 0.247794 0.212149 0.584661 0.045*
C8C 0.2905 (3) 0.26716 (12) 0.63043 (8) 0.0338 (7)
H8C 0.333087 0.235998 0.647417 0.041*
C9C 0.2833 (3) 0.50864 (12) 0.68591 (7) 0.0257 (6)
C10C 0.3343 (3) 0.52404 (12) 0.72614 (7) 0.0343 (6)
H10G 0.459433 0.505401 0.732773 0.051*
H10H 0.233695 0.508211 0.743121 0.051*
H10I 0.343300 0.568623 0.728947 0.051*
C11C 0.1902 (3) 0.65294 (12) 0.64803 (8) 0.0313 (6)
H11C 0.142601 0.637482 0.624474 0.038*
C12C 0.1893 (3) 0.71849 (12) 0.65434 (7) 0.0283 (6)
C13C 0.2803 (3) 0.74474 (12) 0.68581 (7) 0.0320 (6)
H13C 0.346968 0.719386 0.703566 0.038*
C14C 0.2746 (3) 0.80706 (13) 0.69147 (7) 0.0334 (6)
H14C 0.339455 0.823951 0.712986 0.040*
C15C 0.1768 (3) 0.84604 (12) 0.66666 (7) 0.0306 (6)
C16C 0.0857 (3) 0.81969 (13) 0.63528 (8) 0.0337 (6)
H16C 0.017731 0.845106 0.617745 0.040*
C17C 0.0920 (3) 0.75712 (12) 0.62911 (7) 0.0323 (6)
H17C 0.029189 0.740286 0.607343 0.039*
C18C 0.1580 (4) 0.91412 (13) 0.67409 (8) 0.0374 (7)
H18C 0.127176 0.934459 0.649259 0.045*
C20C 0.3418 (4) 0.94350 (14) 0.68993 (10) 0.0564 (9)
H20G 0.449133 0.936685 0.672229 0.085*
H20H 0.373803 0.925118 0.714649 0.085*
H20I 0.320965 0.987609 0.693121 0.085*
C19C −0.0125 (4) 0.92562 (15) 0.70088 (10) 0.0605 (9)
H19G −0.132012 0.909556 0.689354 0.091*
H19H −0.026440 0.969746 0.705235 0.091*
H19I 0.011674 0.904922 0.725218 0.091*
C4′C 0.2228 (3) 0.37429 (12) 0.61818 (7) 0.0263 (6)
C8′C 0.2770 (3) 0.32746 (12) 0.64242 (7) 0.0276 (6)

1 Source of material

The synthesis was performed according to the previously reported procedure [5]. In suspension of 3-acetyl-4-hydroxycoumarin (4.1 g, 20 mmol) in methanol (20 mL), hydrazine hydrate (1 g, 20 mmol) was added and the resulting mixture was refluxed on a water bath. The formed product was filtered and recrystallized from ethanol. A solution of the obtained 3-(1-hydrazonoethyl)-4-hydroxycoumarin (1.1 g, 5 mmol) and 4-isopropylbenzaldehyde (0.74 g, 5 mmol) in absolute ethanol was refluxed for 3 h. After the completion of the reaction, the mixture was allowed to cool to room temperature and the formed precipitate was collected by filtration. A crude solid of 3-(1-(2-(4-isopropylbenzylidene)hydrazinyl)ethylidene)chroman-2,4-dione was purified by flash SiO2 column chromatography (ethyl acetate–hexane, φ(hexane) = 0.5), and dissolved in acetone to form the crystals by slow evaporation of the solvent.

2 Experimental details

Coordinates of hydrogen atoms were introduced in idealized positions and refined using a riding model. Their U iso values were approximated as U iso = kU eq of the carrier atom (k = 1.5 for hydrogen atoms of methyl groups and 1.2 for other hydrogen atoms).

3 Comment

3.1 Chemical context

Azines have attracted a lot of attention from chemists due to their interesting chemical and biological properties, arising from the structure with two of the same or different groups joined by an N–N bond. They show significant in vivo and in vitro biological and pharmacological activities, such as antimicrobial [6], antidepressant [7], anti-inflammatory [8], antioxidant [9], and antitumor [10]. Azines are good synthons in a number of synthetic transformations, especially in the synthesis of heterocyclic systems [11, 12]. In addition, due to the presence of lone electron pairs on nitrogen atoms, they are suitable for the synthesis of various complexes [13], [14], [15]. Here we report the crystal structure of one unsymmetrical azine containing a coumarin core and one more aromatic moiety.

3.2 Structural comment

Asymmetric unit contains three chemically equivalent but crystallographically independent molecules of (Z)-3-(1-(2-((E)-4-isopropylbenzylidene)hydrazinyl)ethylidene) chroman-2,4-dione, designated A, B and C. Pairwise comparison gave no significant differences in bond lengths between A and B ( Δ max  = 2.6σ), A and C ( Δ max  = 1.9σ), and B and C ( Δ max  = 2.4σ) molecules. Bond lengths, valence and torsion angles were found to match those found in compounds with similar fragments, by application of the Mogul knowledge base [16]. The structure of the chromene moiety closely resembles that found in related structure [17]. Intramolecular hydrogen bonds N1A–H1A⋯O3A, N1B–H1B⋯O3B, and N1C–H1C⋯O3C are present in molecules A, B, and C, respectively, which parallels cases found in closely related coumarin-containing azines [18, 19].

Although chemically identical, molecules A, B, and C show some conformational differences, mostly manifested through different torsions around N1–N2, and C11–C12 bonds. With torsion angles τ(C9B–N1B–N2B–C11B) = 177.34(19) ° , and τ(N2B–C11B–C12B–C13B) = – 4.6 ( 3 ) ° molecule B is quite planar (excluding isopropyl group), while molecules A and C are more twisted with torsion angles τ(C9C–N1C–N2C–C11C) = –173.3(2)°, and τ(N2C–C11C–C12C–C13C) =  8.8 ( 4 ) ° for C, and τ(C9A–N1A–N2A–C11A) = –163.7(2)°, and τ(N2A–C11A–C12A–C13A) =  18.9 ( 3 ) ° for A.

Estimation of intermolecular energies by CE–B3LYP method [20] revealed that basic structural motifs are columns of stacked molecules, propagating along crystallographic a axis. There are two crystallographically independent columns – one with ⋯B⋯B⋯ sequence, and other with ⋯C⋯A⋯ ordering. In the BB column, inversion-related molecules B are stacked, with interaction energies E B⋯B(i) = –78 kJ mol−1 and E B⋯B(ii) = –70 kJ mol−1 (symmetry codes (i) –x + 1, –y + 2, –z + 1; (ii) –x + 2, –y + 2, –z + 1). Molecules A and C comprising the AC column appear to be approximately related by noncrystallographic inversion, with interaction energies E A⋯C = –75 kJ mol−1 and E A⋯C(iii) = – 76 kJ mol−1 (symmetry code (iii) –x + 1, –y + 2, –z + 1). In all these interactions, the dispersion component is dominant by a large margin. The redistribution of electron density within the O3–C4–C3–C9 fragment (the O3–C4, C4–C3 and C3–C9 bond lengths) allows us to describe the structure of the studied molecules as superposition of neutral and zwitterionic structures.

Corresponding author: Marko V. Rodić, Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovića 3, 21000, Novi Sad, Serbia, 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: The authors acknowledge the financial support of the Ministry of Education, Science, and Technological Development of the Republic of Serbia, & Austria Federal Ministry of Education, Science and Research (project No. 451-03-02141/2017-09/14; WTZ project No. SRB 14/2018); The Ministry of Science, Technological Development and Innovation of the Republic of Serbia (Grant No. 451-03-47/2023–01/200125); Faculty of Sciences and Mathematics, University of Priština in Kosovska Mitrovica (project No. IJ-0205).

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

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Received: 2023-02-09
Accepted: 2023-03-05
Published Online: 2023-04-13
Published in Print: 2023-06-27

© 2023 the author(s), published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of phenyl(3,3-dichloro-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one)methanone, C7H4Cl2N2O
  4. Crystal structure of poly[diaqua-bis(μ 2-1,4-diaminobutane-N:N′)cobalt(II)] dichloride, C8H28Cl2CoN4O2
  5. Synthesis and crystal structure of (4aR,7S)-7-hydroxy-7-isopropyl-1,1-dimethyldecahydro-2H,6H-8a,4a-(epoxymethano)phenanthren-12-one, C20H32O3
  6. The crystal structure of 1-(2-chlorobenzyl)-3-(3,5-dichlorophenyl)urea, C14H11Cl3N2O
  7. Crystal structure of tetrapropylammonium-1,3,5-thiadiazole-5-amido-2-carbamate – 1,2,4-thiadiazole-3,5-diamine – water (1/1/1), C17H37N9O3S2
  8. Tetrabutylammonium 1,3,5-thiadiazole-5-amido-2-carbamate—1,2,4-thiadiazole-3,5-diamine— water (1/1/1), C21H45N9O3S2
  9. The crystal structure of ((E)-2,4-dichloro-6-(((2-hydroxy-5-nitrophenyl)imino)methyl)phenolato-κ 3 N,O,O′)tris(pyridine-κN)manganese(II), C28H21Cl2MnN5O4
  10. The crystal structure of aqua-bis{2-bromo-6-((2-(2-phenylacetyl)hydrazineylidene)methyl)phenolato-κ3 N,O,O′}-dimethylformamide-κ1 O-erbium(III) chloride – dimethylformamide – water (1/2/1), C39H49N7O9Br2ClEr
  11. Crystal structure of (diaqua-bis(phenanthroline-K 2 N,N′)-tetrakis(m 2-3,4,5,6-tetrafluorophthalato-K 4 O,O:O′:O″;K 2 O:O′)dierbium (III) phenanthroline (1/2), C80H38Er2F16N8O18
  12. Crystal structure of (E)-7-methoxy-2-(4-methoxy-2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C20H17F3O3
  13. The crystal structure of 4–(4,4,5,5–tetramethyl–1,3,2–dioxaborolan–2–yl)morpholine, C10H20BNO3
  14. The crystal structure of catena–poly[aqua(1-naphthoato-κ 2 O,O′)-(μ-1-naphthoato-κ 4 O:O,O′:O′)lead(II)], C22H16O5Pb
  15. The crystal structure of 1-(4-chlorophenyl)-3-cycloheptylurea, C14H19ClN2O
  16. The crystal structure of 4-(pyren-1-yl)butyl-4-nitrobenzoate, C27H21NO4
  17. Crystal structure of cyclo-(bis(µ2-3,3′-(1H-imidazole-3-ium-1,3-diyl)dipropionato-κ4 O,O′:O″,O″′)-dinitrato-κ2 O,O′-tetraoxido-diuranium(VI) C18H22N6O18U2
  18. The crystal structure of catena-[nitrato-κ 2 O,O′-(μ 3-3-iodobenzene-1,2-dicarboxylato-κ 4 O:O′:O″,O‴)-(2,2′:6′,2″-terpyridine-κ 3 N,N′,N″)lanthanum(III)], C23H14IN4O7La
  19. Redetermination of crystal structure of [bis(pyridin-2-ylmethyl)amine-κ 3 N,Nʹ,Nʺ]chloridopalladium(II) chloride monohydrate
  20. Crystal structure of catena-poly[triaqua-[bis(m2-4-(1H-1,2,4-triazol-1-yl)benzoato-k2O:O')-(4-(1H-1,2,4-triazol-1-yl)benzoato-k1O)-praseodymium (III) monohydrate], C27H26N9O10Pr
  21. Crystal structure of trans-diaqua-bis(methyl methylcarbamohydrazonothioato-κ2 N,N′) nickel(II) iodide semihydrate, C6H22N6O2NiS2I2·0.5H2O
  22. The crystal structure of 2-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoindolin-1-one, C17H13F4NOS
  23. The crystal structure of di-μ-1-naphthylacetato-κ 3 O,O′:O;κ 3 O:O,O′-bis[(1-naphthylacetato-κ 2 O,O′)(2,2′-bipyridine-κ 2 N,N′)lead(II)] monohydrate, C68H54N4O9Pb2
  24. Crystal structure of tetrapropylammonium guanidinium 4,4′-sulfonyldibenzoate monohydrate, C27H44N4O7S
  25. Crystal structure of bis(tetrapropylammonium) terephthalate – 1-(diaminomethylene)thiourea – water (1/2/4) C18H40N5O4S
  26. Crystal structure of (E)-7-fluoro-2-(4-morpholinobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C21H20FNO2
  27. The crystal structure of poly[diaqua-bis(μ 3-5-bromobenzene-1,3-dicarboxylato-κ 3 O,O,O′)-(μ 2-1,3-bis-(4-pyridyl)-propane-κ 2 N,N′)-dizinc(II))] – 5-bromobenzene-1,3-dicarboxylic acid [2/1], C37H29Br3N2O14Zn2
  28. The crystal structure of 2-bromo-1,3-phenylene bis(4-methylbenzenesulfonate), C20H17BrO6S2
  29. Crystal structure of europium dichromium icosaaluminum, EuCr2Al20
  30. The crystal structure of N′1,N′3-di((E)-benzylidene) isophthalohydrazide dihydrate, C 22 H 22 N 4 O 4
  31. Crystal structure of 7α,11α-dihydroxy-15-oxo-ent-kauran-16-en-19,6β-olide, C20H26O5
  32. Crystal structure of 4-chloro-N′-[(1E)-pyridin-3-ylmethylidene]benzohydrazide, C13H10ClN3O
  33. The crystal structure of (Z)-3-(1-(2-((E)-4-isopropylbenzylidene)hydrazinyl)ethylidene) chroman-2,4-dione, C21H20N2O3
  34. Crystal structure of E-7-fluoro-2-(2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C18H12F4O
  35. Crystal structure of bis(6-aminopyridine-2-carboxylato–k2O,N)-bis(N,N-dimethylformamide-k1 O)zinc(II), C18H24N6O6Zn
  36. Crystal structure of 5-(adamantan-1-yl)-3-[(4-{[2-(trifluoromethyl)phenyl]-methyl}piperazin-1-yl)methyl]-1,3,4-oxadiazole-2(3H)-thione, C25H31F3N4OS
  37. Crystal structure of tetrapropylammonium bicarbonate–1-(diaminomethylene)thiourea – water (2/2/1), C30H72N10O7S2
  38. Crystal structure of tris(2,2′-bipyridine-κ2 N,N′)iron(II) triiodide – dichloromethane (2/1), C61H50Cl2Fe2I12N12
  39. Crystal structure of 2-amino-3-[2-(1,3,3-trimethyl-1,3-dihydro-indol-2-ylidene)-ethylideneamino]-but-2-enedinitrile, C17H17N5
  40. The crystal structure of 1-(2-chlorophenyl)-3-cycloheptylurea, C14H19ClN2O
  41. Crystal structure of potassium bis(pentaselenido-κ 2 Se 1,Se 5)palladate(II), K2[Pd(Se5)2]
  42. The crystal structure of 5,10-bis(2-methoxyethyl)-5,10-dihydro-[1,2,3,4]tetrathiocino[5,6-b:8, 7-b′]diindole, C22H22N2O2S4
  43. The crystal structure of 4-(4-iodophenyl)-5H-1,2,3-dithiazole-5-thione, C8H4INS3
  44. Crystal structure of bis{μ2-(4-acetyl-phenoxy)acetato-κ2 O:O′}-bis{μ2-(4-acetyl-phenoxy)acetato-κ3 O,O′:O)- bis{(4-acetyl-phenoxy)acetato-κ2 O,O′}-bis(phenanthrolin-κ2 N,N′)didysprosium(III) tetrahydrate, C84H78N4O28Dy2
  45. Crystal structure of Eu2Pd3.37(1)Zn13.63(1)
  46. Crystal structure of 2-methoxy-4-(methoxy-carbonyl)phenyl 2-chloro-4-fluorobenzoate, C16H12ClFO5
  47. Crystal structure of catena-poly[bis(μ2-dicyanamide-κ2 N:N′)-bis(4-vinylpyridine-κN)-copper(II)], C18H14CuN8
  48. The crystal structure of iguratimod-dimethylformamide (1/1), C17H14N2O6S·C3H7NO
  49. Synthesis and crystal structure of 1-((3R,10S,13S,17S)-10,13-dimethyl-3-(m-tolylamino)hexadecahydro-1H-cyclopenta[α]phenanthren-17-yl)ethan-1-one, C28H41NO
  50. The crystal structure of diaqua-bis(4-bromo-2-formylphenoxy)zinc(II), C14H12Br2O6Zn
  51. The crystal structure of tetra(1-ethylimidazole-κ 1 N)-[μ 4-imidazole-4,5-dicarboxylato-κ 4 O, N, O′, N′]-trioxido-divanadium, C25H33N10O7V2
  52. The crystal structure of (E)-N′-(1-(4-fluorophenyl)propylidene)-2-hydroxybenzohydrazide, C16H15FN2O2
https://doi.org/10.1515/ncrs-2023-0062
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Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of phenyl(3,3-dichloro-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one)methanone, C7H4Cl2N2O
  4. Crystal structure of poly[diaqua-bis(μ 2-1,4-diaminobutane-N:N′)cobalt(II)] dichloride, C8H28Cl2CoN4O2
  5. Synthesis and crystal structure of (4aR,7S)-7-hydroxy-7-isopropyl-1,1-dimethyldecahydro-2H,6H-8a,4a-(epoxymethano)phenanthren-12-one, C20H32O3
  6. The crystal structure of 1-(2-chlorobenzyl)-3-(3,5-dichlorophenyl)urea, C14H11Cl3N2O
  7. Crystal structure of tetrapropylammonium-1,3,5-thiadiazole-5-amido-2-carbamate – 1,2,4-thiadiazole-3,5-diamine – water (1/1/1), C17H37N9O3S2
  8. Tetrabutylammonium 1,3,5-thiadiazole-5-amido-2-carbamate—1,2,4-thiadiazole-3,5-diamine— water (1/1/1), C21H45N9O3S2
  9. The crystal structure of ((E)-2,4-dichloro-6-(((2-hydroxy-5-nitrophenyl)imino)methyl)phenolato-κ 3 N,O,O′)tris(pyridine-κN)manganese(II), C28H21Cl2MnN5O4
  10. The crystal structure of aqua-bis{2-bromo-6-((2-(2-phenylacetyl)hydrazineylidene)methyl)phenolato-κ3 N,O,O′}-dimethylformamide-κ1 O-erbium(III) chloride – dimethylformamide – water (1/2/1), C39H49N7O9Br2ClEr
  11. Crystal structure of (diaqua-bis(phenanthroline-K 2 N,N′)-tetrakis(m 2-3,4,5,6-tetrafluorophthalato-K 4 O,O:O′:O″;K 2 O:O′)dierbium (III) phenanthroline (1/2), C80H38Er2F16N8O18
  12. Crystal structure of (E)-7-methoxy-2-(4-methoxy-2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C20H17F3O3
  13. The crystal structure of 4–(4,4,5,5–tetramethyl–1,3,2–dioxaborolan–2–yl)morpholine, C10H20BNO3
  14. The crystal structure of catena–poly[aqua(1-naphthoato-κ 2 O,O′)-(μ-1-naphthoato-κ 4 O:O,O′:O′)lead(II)], C22H16O5Pb
  15. The crystal structure of 1-(4-chlorophenyl)-3-cycloheptylurea, C14H19ClN2O
  16. The crystal structure of 4-(pyren-1-yl)butyl-4-nitrobenzoate, C27H21NO4
  17. Crystal structure of cyclo-(bis(µ2-3,3′-(1H-imidazole-3-ium-1,3-diyl)dipropionato-κ4 O,O′:O″,O″′)-dinitrato-κ2 O,O′-tetraoxido-diuranium(VI) C18H22N6O18U2
  18. The crystal structure of catena-[nitrato-κ 2 O,O′-(μ 3-3-iodobenzene-1,2-dicarboxylato-κ 4 O:O′:O″,O‴)-(2,2′:6′,2″-terpyridine-κ 3 N,N′,N″)lanthanum(III)], C23H14IN4O7La
  19. Redetermination of crystal structure of [bis(pyridin-2-ylmethyl)amine-κ 3 N,Nʹ,Nʺ]chloridopalladium(II) chloride monohydrate
  20. Crystal structure of catena-poly[triaqua-[bis(m2-4-(1H-1,2,4-triazol-1-yl)benzoato-k2O:O')-(4-(1H-1,2,4-triazol-1-yl)benzoato-k1O)-praseodymium (III) monohydrate], C27H26N9O10Pr
  21. Crystal structure of trans-diaqua-bis(methyl methylcarbamohydrazonothioato-κ2 N,N′) nickel(II) iodide semihydrate, C6H22N6O2NiS2I2·0.5H2O
  22. The crystal structure of 2-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoindolin-1-one, C17H13F4NOS
  23. The crystal structure of di-μ-1-naphthylacetato-κ 3 O,O′:O;κ 3 O:O,O′-bis[(1-naphthylacetato-κ 2 O,O′)(2,2′-bipyridine-κ 2 N,N′)lead(II)] monohydrate, C68H54N4O9Pb2
  24. Crystal structure of tetrapropylammonium guanidinium 4,4′-sulfonyldibenzoate monohydrate, C27H44N4O7S
  25. Crystal structure of bis(tetrapropylammonium) terephthalate – 1-(diaminomethylene)thiourea – water (1/2/4) C18H40N5O4S
  26. Crystal structure of (E)-7-fluoro-2-(4-morpholinobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C21H20FNO2
  27. The crystal structure of poly[diaqua-bis(μ 3-5-bromobenzene-1,3-dicarboxylato-κ 3 O,O,O′)-(μ 2-1,3-bis-(4-pyridyl)-propane-κ 2 N,N′)-dizinc(II))] – 5-bromobenzene-1,3-dicarboxylic acid [2/1], C37H29Br3N2O14Zn2
  28. The crystal structure of 2-bromo-1,3-phenylene bis(4-methylbenzenesulfonate), C20H17BrO6S2
  29. Crystal structure of europium dichromium icosaaluminum, EuCr2Al20
  30. The crystal structure of N′1,N′3-di((E)-benzylidene) isophthalohydrazide dihydrate, C 22 H 22 N 4 O 4
  31. Crystal structure of 7α,11α-dihydroxy-15-oxo-ent-kauran-16-en-19,6β-olide, C20H26O5
  32. Crystal structure of 4-chloro-N′-[(1E)-pyridin-3-ylmethylidene]benzohydrazide, C13H10ClN3O
  33. The crystal structure of (Z)-3-(1-(2-((E)-4-isopropylbenzylidene)hydrazinyl)ethylidene) chroman-2,4-dione, C21H20N2O3
  34. Crystal structure of E-7-fluoro-2-(2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C18H12F4O
  35. Crystal structure of bis(6-aminopyridine-2-carboxylato–k2O,N)-bis(N,N-dimethylformamide-k1 O)zinc(II), C18H24N6O6Zn
  36. Crystal structure of 5-(adamantan-1-yl)-3-[(4-{[2-(trifluoromethyl)phenyl]-methyl}piperazin-1-yl)methyl]-1,3,4-oxadiazole-2(3H)-thione, C25H31F3N4OS
  37. Crystal structure of tetrapropylammonium bicarbonate–1-(diaminomethylene)thiourea – water (2/2/1), C30H72N10O7S2
  38. Crystal structure of tris(2,2′-bipyridine-κ2 N,N′)iron(II) triiodide – dichloromethane (2/1), C61H50Cl2Fe2I12N12
  39. Crystal structure of 2-amino-3-[2-(1,3,3-trimethyl-1,3-dihydro-indol-2-ylidene)-ethylideneamino]-but-2-enedinitrile, C17H17N5
  40. The crystal structure of 1-(2-chlorophenyl)-3-cycloheptylurea, C14H19ClN2O
  41. Crystal structure of potassium bis(pentaselenido-κ 2 Se 1,Se 5)palladate(II), K2[Pd(Se5)2]
  42. The crystal structure of 5,10-bis(2-methoxyethyl)-5,10-dihydro-[1,2,3,4]tetrathiocino[5,6-b:8, 7-b′]diindole, C22H22N2O2S4
  43. The crystal structure of 4-(4-iodophenyl)-5H-1,2,3-dithiazole-5-thione, C8H4INS3
  44. Crystal structure of bis{μ2-(4-acetyl-phenoxy)acetato-κ2 O:O′}-bis{μ2-(4-acetyl-phenoxy)acetato-κ3 O,O′:O)- bis{(4-acetyl-phenoxy)acetato-κ2 O,O′}-bis(phenanthrolin-κ2 N,N′)didysprosium(III) tetrahydrate, C84H78N4O28Dy2
  45. Crystal structure of Eu2Pd3.37(1)Zn13.63(1)
  46. Crystal structure of 2-methoxy-4-(methoxy-carbonyl)phenyl 2-chloro-4-fluorobenzoate, C16H12ClFO5
  47. Crystal structure of catena-poly[bis(μ2-dicyanamide-κ2 N:N′)-bis(4-vinylpyridine-κN)-copper(II)], C18H14CuN8
  48. The crystal structure of iguratimod-dimethylformamide (1/1), C17H14N2O6S·C3H7NO
  49. Synthesis and crystal structure of 1-((3R,10S,13S,17S)-10,13-dimethyl-3-(m-tolylamino)hexadecahydro-1H-cyclopenta[α]phenanthren-17-yl)ethan-1-one, C28H41NO
  50. The crystal structure of diaqua-bis(4-bromo-2-formylphenoxy)zinc(II), C14H12Br2O6Zn
  51. The crystal structure of tetra(1-ethylimidazole-κ 1 N)-[μ 4-imidazole-4,5-dicarboxylato-κ 4 O, N, O′, N′]-trioxido-divanadium, C25H33N10O7V2
  52. The crystal structure of (E)-N′-(1-(4-fluorophenyl)propylidene)-2-hydroxybenzohydrazide, C16H15FN2O2
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