Startseite Crystal structure of 4-chloro-N′-[(1E)-pyridin-3-ylmethylidene]benzohydrazide, C13H10ClN3O
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Crystal structure of 4-chloro-N′-[(1E)-pyridin-3-ylmethylidene]benzohydrazide, C13H10ClN3O

  • Lamya H. Al-Wahaibi , Olivier Blacque , Edward R. T. Tiekink ORCID logo und Ali A. El-Emam ORCID logo EMAIL logo
Veröffentlicht/Copyright: 8. März 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

C13H10ClN3O, monoclinic, P21/c (no. 14), a = 19.0933(2) Å, b = 23.0910(3) Å, c = 10.6831(2) Å, β = 90.064(1)°, V = 4710.00(12) Å3, Z = 16, R gt (F) = 0.0411, wR ref (F 2) = 0.1081, T = 160 K.

CCDC no.: 2233777

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: Colourless plate
Size: 0.16 × 0.06 × 0.03 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 2.80 mm−1
Diffractometer, scan mode: XtaLAB Synergy
θ max, completeness: 74.5°, 99%
N(hkl)measured, N(hkl)unique, R int: 49,867, 9505, 0.060
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 8033
N(param)refined: 667
Programs: CrysAlis PRO [1], Shelx [2, 3], WinGX/Ortep [4]
Table 2:

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

Atom x y z U iso*/U eq
Cl1 0.59359 (4) 1.04498 (3) 0.12812 (9) 0.0508 (2)
O1 0.81695 (11) 0.83009 (9) 0.01032 (17) 0.0418 (5)
N1 0.81780 (10) 0.82111 (9) 0.22192 (19) 0.0253 (4)
H1N 0.8052 (16) 0.8318 (13) 0.299 (3) 0.037 (8)*
N2 0.86948 (9) 0.77919 (8) 0.21536 (19) 0.0258 (4)
N3 1.02511 (10) 0.66183 (9) 0.45775 (19) 0.0284 (4)
C1 0.65304 (13) 0.98756 (11) 0.1273 (3) 0.0357 (6)
C2 0.69210 (13) 0.97746 (12) 0.0217 (3) 0.0370 (6)
H2 0.687848 1.001986 −0.049335 0.044*
C3 0.73779 (13) 0.93090 (12) 0.0205 (2) 0.0340 (6)
H3 0.764485 0.923116 −0.052631 0.041*
C4 0.74516 (11) 0.89532 (10) 0.1249 (2) 0.0258 (5)
C5 0.70582 (12) 0.90698 (11) 0.2315 (2) 0.0298 (5)
H5 0.710965 0.883442 0.303896 0.036*
C6 0.65907 (13) 0.95302 (11) 0.2322 (3) 0.0361 (6)
H6 0.631453 0.960677 0.304244 0.043*
C7 0.79607 (12) 0.84577 (11) 0.1136 (2) 0.0283 (5)
C8 0.88926 (12) 0.75792 (11) 0.3202 (2) 0.0270 (5)
H8 0.867406 0.770135 0.395525 0.032*
C9 0.94552 (11) 0.71479 (10) 0.3244 (2) 0.0245 (5)
C10 0.97166 (12) 0.69866 (11) 0.4408 (2) 0.0283 (5)
H10 0.950236 0.714787 0.513076 0.034*
C11 1.05365 (12) 0.63894 (10) 0.3541 (2) 0.0277 (5)
H11 1.091646 0.612743 0.363559 0.033*
C12 1.03072 (12) 0.65145 (10) 0.2344 (2) 0.0273 (5)
H12 1.052461 0.634029 0.163883 0.033*
C13 0.97570 (12) 0.68966 (10) 0.2188 (2) 0.0267 (5)
H13 0.958728 0.698652 0.137426 0.032*
Cl2 −0.17512 (3) 1.03769 (3) 0.29158 (8) 0.04596 (18)
O2 0.05856 (11) 0.83464 (10) 0.44291 (18) 0.0454 (5)
N4 0.06562 (10) 0.82269 (9) 0.2330 (2) 0.0277 (4)
H4N 0.0517 (16) 0.8318 (14) 0.154 (3) 0.040 (8)*
N5 0.11736 (10) 0.78179 (9) 0.24757 (19) 0.0275 (4)
N6 0.27438 (11) 0.65524 (10) 0.0344 (2) 0.0318 (5)
C14 −0.11112 (12) 0.98401 (11) 0.3011 (3) 0.0332 (5)
C15 −0.08093 (15) 0.97208 (12) 0.4151 (3) 0.0400 (6)
H15 −0.093630 0.993681 0.487274 0.048*
C16 −0.03174 (14) 0.92815 (12) 0.4234 (2) 0.0354 (6)
H16 −0.011138 0.919326 0.502082 0.042*
C17 −0.01203 (12) 0.89665 (10) 0.3175 (2) 0.0274 (5)
C18 −0.04248 (13) 0.91051 (11) 0.2036 (3) 0.0325 (5)
H18 −0.028996 0.889845 0.130590 0.039*
C19 −0.09222 (13) 0.95398 (11) 0.1942 (3) 0.0340 (5)
H19 −0.113015 0.963016 0.115805 0.041*
C20 0.04038 (13) 0.84914 (11) 0.3376 (2) 0.0297 (5)
C21 0.13624 (12) 0.75560 (11) 0.1475 (2) 0.0285 (5)
H21 0.113513 0.763837 0.070352 0.034*
C22 0.19281 (12) 0.71303 (10) 0.1522 (2) 0.0263 (5)
C23 0.21919 (13) 0.69105 (11) 0.0409 (2) 0.0298 (5)
H23 0.196880 0.701990 −0.035024 0.036*
C24 0.30306 (12) 0.63875 (11) 0.1430 (2) 0.0315 (5)
H24 0.342417 0.613616 0.140205 0.038*
C25 0.27879 (13) 0.65615 (11) 0.2595 (2) 0.0305 (5)
H25 0.299722 0.642027 0.334233 0.037*
C26 0.22351 (13) 0.69448 (11) 0.2638 (2) 0.0292 (5)
H26 0.206470 0.708119 0.341979 0.035*
Cl3 0.08214 (3) 1.03786 (3) 0.21099 (8) 0.04106 (16)
O3 0.30269 (10) 0.82449 (9) 0.05898 (17) 0.0381 (4)
N7 0.32103 (10) 0.82356 (9) 0.2694 (2) 0.0271 (4)
H7N 0.3076 (15) 0.8339 (13) 0.348 (3) 0.036 (8)*
N8 0.37216 (10) 0.78150 (9) 0.25922 (19) 0.0275 (4)
N9 0.52135 (10) 0.65395 (9) 0.4889 (2) 0.0296 (4)
C27 0.14266 (12) 0.98153 (10) 0.2002 (3) 0.0305 (5)
C28 0.14180 (14) 0.94615 (11) 0.0960 (3) 0.0340 (5)
H28 0.108069 0.952010 0.031786 0.041*
C29 0.19058 (13) 0.90211 (11) 0.0860 (2) 0.0325 (5)
H29 0.190897 0.878239 0.013623 0.039*
C30 0.23923 (12) 0.89236 (10) 0.1810 (2) 0.0261 (5)
C31 0.23839 (13) 0.92840 (11) 0.2849 (2) 0.0319 (5)
H31 0.270924 0.921952 0.350757 0.038*
C32 0.19099 (13) 0.97365 (12) 0.2943 (3) 0.0345 (5)
H32 0.191854 0.998821 0.364676 0.041*
C33 0.29055 (12) 0.84407 (11) 0.1626 (2) 0.0269 (5)
C34 0.38992 (11) 0.75695 (10) 0.3616 (2) 0.0273 (5)
H34 0.366949 0.766978 0.437392 0.033*
C35 0.44551 (12) 0.71345 (10) 0.3623 (2) 0.0257 (5)
C36 0.46772 (12) 0.69104 (10) 0.4761 (2) 0.0283 (5)
H36 0.443454 0.702664 0.549461 0.034*
C37 0.55412 (12) 0.63711 (11) 0.3841 (2) 0.0301 (5)
H37 0.592423 0.611049 0.391118 0.036*
C38 0.53468 (13) 0.65593 (11) 0.2663 (2) 0.0310 (5)
H38 0.558770 0.642451 0.194224 0.037*
C39 0.47991 (12) 0.69451 (11) 0.2546 (2) 0.0279 (5)
H39 0.465818 0.707992 0.174426 0.033*
Cl4 0.35255 (4) 1.04736 (3) 0.36861 (9) 0.0527 (2)
O4 0.55725 (10) 0.81752 (8) 0.45932 (17) 0.0363 (4)
N10 0.56900 (10) 0.82025 (9) 0.2477 (2) 0.0260 (4)
H10N 0.5583 (17) 0.8348 (14) 0.174 (3) 0.044 (9)*
N11 0.62016 (10) 0.77791 (9) 0.25057 (18) 0.0263 (4)
N12 0.77016 (10) 0.66277 (9) −0.00942 (19) 0.0281 (4)
C40 0.40712 (13) 0.98701 (11) 0.3610 (3) 0.0374 (6)
C41 0.42203 (19) 0.95691 (13) 0.4692 (3) 0.0533 (9)
H41 0.402978 0.969116 0.546921 0.064*
C42 0.46483 (17) 0.90893 (13) 0.4635 (3) 0.0451 (7)
H42 0.474520 0.887993 0.538090 0.054*
C43 0.49400 (11) 0.89049 (10) 0.3521 (2) 0.0274 (5)
C44 0.47856 (14) 0.92169 (13) 0.2441 (3) 0.0380 (6)
H44 0.497893 0.909873 0.166278 0.046*
C45 0.43515 (14) 0.96996 (13) 0.2489 (3) 0.0417 (6)
H45 0.424953 0.991047 0.174764 0.050*
C46 0.54228 (12) 0.83948 (11) 0.3585 (2) 0.0279 (5)
C47 0.64068 (12) 0.75953 (10) 0.1438 (2) 0.0279 (5)
H47 0.619606 0.774414 0.069887 0.033*
C48 0.69598 (11) 0.71606 (10) 0.1334 (2) 0.0241 (4)
C49 0.71806 (12) 0.70012 (10) 0.0140 (2) 0.0264 (5)
H49 0.694571 0.716879 −0.055533 0.032*
C50 0.80208 (12) 0.63944 (10) 0.0905 (2) 0.0279 (5)
H50 0.839551 0.613170 0.076552 0.033*
C51 0.78344 (12) 0.65153 (11) 0.2122 (2) 0.0289 (5)
H51 0.807231 0.633411 0.279841 0.035*
C52 0.72991 (12) 0.69020 (11) 0.2350 (2) 0.0274 (5)
H52 0.716338 0.699107 0.318319 0.033*

1 Source of material

Nicotinaldehyde (1.07 g, 0.01 mol) was added to a stirred suspension of 4-chlorobenzohydrazide (1.71 g, 0.01 mol), in ethanol (10 mL), and the mixture was heated under reflux for 1 h. On cooling, the precipitated crude product was filtered, washed with ethanol, dried and recrystallised from ethanol to yield 2.44 g (94%) of the title compound as colourless plates. Melting point: 491–493 K (uncorrected). 1 H NMR (DMSO-d 6 , 500.13 MHz): d 11.02 (s, 1H, NH), 9.05 (CH=N), 8.99 (s, 1H, Pyridine–H), 8.48–8.62 (m, 2H, Pyridine–H), 7.96 (d, 2H, Ar–H, J = 7.2 Hz) and 7.45–7.59 (m, 2H, Ar–H & 1 Pyridine–H). 13 C NMR (DMSO-d 6 , 125.76 MHz): d 161.24 (C=O), 152.28, 149.20, 134.54, 129.80, 123.90 (Pyridine–C), 144.66 (CH=N), 138.0, 132.24, 130.08, 127.54 (Ar–C). Analysis (%) for C13H10ClN3O (259.69): C, 58.11 (Calc. 58.06); H, 4.14 (Calc. 4.18); N, 15.64 (Calc. 15.57).

2 Experimental details

The C-bound H atoms were geometrically placed (C–H = 0.95 Å) and refined as riding with U iso(H) = 1.2U eq(C). The N-bound H atoms were located in a difference map and refined freely. The crystal was refined as a two-component twin with the minor component = 0.2253(9).

3 Comment

Hydrazides and their N′-arylidene derivatives receive considerable interest for their remarkable biological activities [5, 6]. In addition, carbohydrazide-hydrazone derivatives are utilised as efficient intermediates for the synthesis of several biologically-active heterocyclic compounds [7, 8].

The synthesis and the crystal structure of a new N′-arylidene hydrazide derivative (I) are described herein along with an analysis of the molecular packing.

The molecular structures of the four independent molecules comprising the asymmetric-unit of (I) are shown in the upper four images of the figure (50% probability ellipsoids).

While to a first approximation, the molecules are similar to each other, having a strictly planar, central CN2O residue, are C-connected to a 4-chlorophenyl and to a 3-pyridyl residue via the imine bond, conformational differences are evident as shown in the overlay diagram (the color code for the O1- to O4-containing molecules is red, green, blue and pink, respectively; the images were overlaid so the 3-pyridyl rings are coincident). A small twist is noted about the C8–C9 bond as seen in the value of the N2–C8–C9–C10 torsion angle of 171.5(2)°, suggesting this part of the molecule is relatively planar; the comparable values for the O2- to O4-containing molecules are –171.1(2)°, 174.7(2)° and –176.9(2)°, respectively. A greater twist is seen about the C4–C7 bond, i.e. C5–C4–C7–O1 = 163.5(2)°; the values for the O2- to O4-containing molecules are −170.8(3)°, −159.0(2)° and 174.0(3)°, respectively. These differences manifest in a range of dihedral angles between the terminal rings, i.e. 25.04(11)°, 11.79(12)°, 32.82(12)° and 15.16(12)°, respectively. While the differences in conformation confirm the choice of crystal symmetry, these are unlikely to have any chemical significance.

There are three closely related 3-pyridyl derivatives in the literature, which differ only in the nature of the substitution at the 4-position of the phenyl ring, i.e. with H [9], NMe2 [10] and NO2 [11] cf. Cl in (I). For comparison with (I), the values of the dihedral angles between the terminal rings are 47.79(14)°, 5.19(8)° and 28.29(4)°, respectively, highlighting the variability of conformations in this class of compound, at least in the solid-state. The occurrence of a Z' > 1 is not unusual in this class of compounds [12].

A supramolecular chain featuring amide-N–H⋯N(pyridyl) hydrogen bonds is prominent in the molecular packing, as illustrated in the lower view of the figure. The chains involve all four independent molecules [a representative interaction is H1n⋯N12 i [N1–H1n⋯N12 i : H1n⋯N12 i  = 2.16(3) Å, N1⋯N12 i  = 3.035(3) Å with angle at H1n = 167(3)° for symmetry operation (i): x, 3/2 − y, 1/2 + z].

Molecules assemble into supramolecular layers in the ac-plane. Prominent interactions between the twisted chains along the a-axis include pyridyl-C–H⋯O(carbonyl) [C12–H12⋯O2 ii : H12⋯O2 ii  = 2.47 Å, C12⋯O2 ii  = 3.176(3) Å with angle at H12 = 131° for (ii): 1 + x, 3/2 − y, −1/2 + z] and pyridyl-C–H⋯N(imine) [C49–H49⋯N11 i : H49⋯N11 i = 2.51 Å, C49⋯N11 i  = 3.415(3) Å with angle at H49 = 158°] interactions. The 4-chlorophenyl rings project alternatively to either side of the layer and these inter-digitate with adjacent layers along the b-axis with close phenyl-C–Cl⋯π(phenyl, pyridyl) contacts [closest contact: C1–Cl1⋯Cg(N9-pyridyl) iii : Cl1⋯Cg(N9-pyridyl) iii  = 3.4860(12) Å with angle at Cl1 = 170.47(9)° for (iii): 1 − x, 1/2 + y, 1/2 − z].

Corresponding author: Ali A. El-Emam, Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt, 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: Princess Nourah bint Abdulrahman University Researchers Supporting Project No. (PNURSP2023R3), Princess Nourah bint Abdulrahman University, Riyadh, Saudi Arabia.

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

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Received: 2023-02-08
Accepted: 2023-02-27
Published Online: 2023-03-08
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

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  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-2023-0060
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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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Heruntergeladen am 15.11.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2023-0060/html
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