Startseite Crystal structure of 7-(dimethylamino)-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-ethyl carboxylate, C15H16F3NO4
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Crystal structure of 7-(dimethylamino)-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-ethyl carboxylate, C15H16F3NO4

  • Ruifeng Yue EMAIL logo , Ruiying Wang , Hang Shu , Dayong Fu und Zhuanghui Qi
Veröffentlicht/Copyright: 27. Januar 2025
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Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 240 Heft 2

Abstract

C15H16F3NO4, triclinic, P 1 ‾ (no. 2), a = 6.7000(2) Å, b = 11.7844(4) Å, c = 19.3039(6) Å, α = 83.581(3)°, β = 86.015(3)°; γ = 87.713(3)°; V = 1510.14 Å3, Z = 4, R gt (F) = 0.0459, wRref(F2) = 0.1389, T = 294.95 K.

CCDC no.: 2406237

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: Green block
Size: 0.30 × 0.28 × 0.18 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 1.12 mm−1
Diffractometer, scan mode: SuperNova, ω
θmax, completeness: 71.5°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 12143, 5735, 0.020
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 4,731
N(param)refined: 443
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 Uiso*/Ueq
F1 −0.25204 (18) 0.76590 (11) 0.10761 (7) 0.0810 (4)
F2 −0.0468 (2) 0.88036 (10) 0.04791 (7) 0.0849 (4)
F3 0.0509 (2) 0.77173 (12) 0.13674 (6) 0.0830 (4)
O1 −0.02201 (15) 0.57825 (10) 0.07778 (6) 0.0512 (3)
O2 −0.13767 (18) 0.68448 (12) −0.01389 (6) 0.0592 (3)
H2 −0.0919 0.7151 −0.0516 0.089*
O3 0.1256 (2) 0.80847 (15) −0.10034 (7) 0.0799 (5)
O4 0.4233 (2) 0.83167 (13) −0.06084 (7) 0.0717 (4)
N1 0.1920 (3) 0.29191 (13) 0.25195 (8) 0.0604 (4)
C1 0.0030 (2) 0.68309 (13) 0.03483 (8) 0.0437 (3)
C2 0.2160 (2) 0.70113 (14) 0.00482 (8) 0.0457 (4)
C3 0.3675 (2) 0.63964 (14) 0.03413 (8) 0.0472 (4)
H3 0.4984 0.6545 0.0173 0.057*
C4 0.3323 (2) 0.55181 (14) 0.09069 (8) 0.0449 (3)
C5 0.4824 (2) 0.48718 (16) 0.12521 (10) 0.0552 (4)
H5 0.6156 0.5023 0.1119 0.066*
C6 0.4394 (3) 0.40230 (16) 0.17803 (10) 0.0566 (4)
H6 0.5433 0.3618 0.2002 0.068*
C7 0.2386 (3) 0.37554 (13) 0.19920 (8) 0.0477 (4)
C8 0.0871 (2) 0.43842 (13) 0.16353 (8) 0.0449 (3)
H8 −0.0464 0.4220 0.1753 0.054*
C9 0.1352 (2) 0.52395 (13) 0.11133 (8) 0.0414 (3)
C10 0.3437 (4) 0.23497 (18) 0.29471 (11) 0.0730 (6)
H10A 0.4358 0.1925 0.2663 0.110*
H10B 0.2811 0.1838 0.3312 0.110*
H10C 0.4148 0.2909 0.3149 0.110*
C11 −0.0154 (3) 0.27141 (19) 0.27426 (12) 0.0746 (6)
H11A −0.0764 0.3388 0.2914 0.112*
H11B −0.0224 0.2090 0.3108 0.112*
H11C −0.0851 0.2528 0.2354 0.112*
C12 −0.0619 (3) 0.77639 (16) 0.08199 (10) 0.0587 (4)
C13 0.2471 (3) 0.78469 (16) −0.05705 (9) 0.0542 (4)
C14a 0.4567 (10) 0.9236 (5) −0.1186 (2) 0.0726 (13)
H14Aa 0.4915 0.8909 −0.1620 0.087*
H14Ba 0.3356 0.9707 −0.1243 0.087*
C15a 0.6182 (9) 0.9926 (6) −0.1024 (4) 0.0931 (17)
H15Aa 0.6660 1.0388 −0.1438 0.140*
H15Ba 0.7255 0.9435 −0.0848 0.140*
H15Ca 0.5700 1.0410 −0.0676 0.140*
F4 0.61872 (19) 0.13185 (11) 0.42112 (6) 0.0728 (3)
F5 0.93038 (18) 0.13384 (12) 0.44069 (7) 0.0842 (4)
F6 0.7345 (2) 0.02022 (10) 0.50549 (7) 0.0760 (3)
O5 0.72341 (16) 0.32348 (10) 0.47936 (6) 0.0518 (3)
O6 0.85351 (17) 0.21275 (12) 0.56633 (7) 0.0624 (4)
H6A 0.8242 0.1693 0.6015 0.094*
O7 0.61327 (19) 0.08050 (13) 0.65234 (7) 0.0679 (4)
O8 0.28423 (17) 0.11278 (10) 0.64710 (6) 0.0525 (3)
N2 0.4889 (3) 0.60856 (13) 0.30756 (8) 0.0603 (4)
C00L 0.5627 (2) 0.37775 (13) 0.44773 (8) 0.0417 (3)
C16 0.7007 (2) 0.21732 (14) 0.52123 (8) 0.0460 (4)
C17 0.4929 (2) 0.20471 (13) 0.55780 (8) 0.0418 (3)
C18 0.3383 (2) 0.26640 (13) 0.53052 (8) 0.0428 (3)
H18 0.2094 0.2542 0.5504 0.051*
C19 0.3674 (2) 0.35014 (13) 0.47172 (8) 0.0428 (3)
C20 0.2126 (2) 0.41401 (15) 0.43883 (9) 0.0514 (4)
H20 0.0805 0.3990 0.4540 0.062*
C21 0.2504 (3) 0.49776 (15) 0.38509 (10) 0.0551 (4)
H21 0.1440 0.5376 0.3641 0.066*
C22 0.4486 (3) 0.52480 (13) 0.36098 (8) 0.0481 (4)
C23 0.6053 (2) 0.46239 (13) 0.39464 (8) 0.0470 (4)
H23 0.7377 0.4787 0.3808 0.056*
C24 0.6923 (4) 0.62894 (18) 0.28064 (11) 0.0717 (6)
H24A 0.7682 0.6510 0.3170 0.108*
H24B 0.6926 0.6889 0.2426 0.108*
H24C 0.7512 0.5604 0.2643 0.108*
C25 0.3285 (4) 0.66528 (17) 0.26848 (11) 0.0707 (6)
H25A 0.2570 0.6095 0.2483 0.106*
H25B 0.3841 0.7193 0.2320 0.106*
H25C 0.2384 0.7045 0.2993 0.106*
C26 0.7465 (3) 0.12477 (16) 0.47182 (10) 0.0573 (4)
C27 0.4733 (2) 0.12698 (14) 0.62234 (8) 0.0472 (4)
C28 0.2579 (3) 0.04071 (17) 0.71284 (9) 0.0603 (5)
H28A 0.3353 0.0686 0.7477 0.072*
H28B 0.3036 −0.0370 0.7069 0.072*
C29 0.0432 (3) 0.0434 (2) 0.73559 (11) 0.0741 (6)
H29A −0.0317 0.0135 0.7015 0.111*
H29B −0.0012 0.1207 0.7404 0.111*
H29C 0.0228 −0.0024 0.7797 0.111*
C14Ab 0.515 (2) 0.8860 (15) −0.1260 (6) 0.076 (3)
H14Cb 0.5545 0.8256 −0.1550 0.091*
H14Db 0.4109 0.9319 −0.1493 0.091*
C15Ab 0.6589 (19) 0.9466 (16) −0.1267 (8) 0.087 (4)
H15Db 0.6499 1.0082 −0.1635 0.131*
H15Eb 0.7800 0.9021 −0.1346 0.131*
H15Fb 0.6602 0.9770 −0.0827 0.131*

  1. aOccupancy: 0.702 (18), bOccupancy: 0.298 (18).

1 Source of material

The title compound, 7-(dimethylamino)-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-ethyl carboxylate was synthesized according to the literature method with slight modification. 5 Anhydrous ethanol was selected as the reaction solvent for the condensation between 4-dimethylaminosalicylaldehyde and ethyl trifluoroacetoacetate, by which the synthetic yield can be increased more higher than reagent grade ethanol. In a 100 mL round bottom flask, 4-dimethylaminosalicylaldehyde (826 mg, 5 mmol) and ethyl trifluoroacetoacetate (1.013 g, 5.5 mmol) was dissolved in 60 mL anhydrous ethanol. Piperidine (0.04 mmol) was added and the mixture was heated to reflux for about 5 h. The reaction progress was monitored with thin layer chromatography (TLC). When the starting 4-dimethylaminosalicylaldehyde disappeared completely on the TLC plate, the reaction was quenched by adding distilled water 40 mL. The reaction mixture was extracted with dichloromethane (50 mL × 3). The organic part was combined and washed with distilled water (500 mL × 3). The collected organic phase was dried over MgSO4. The volatile components were evaporated on the rotary evaporating equipment. The residue was purified by column chromatography on silica gel (hexane/dichloromethane, 1:2). The purified 7-(dimethylamino)-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-ethyl carboxylate was saturated in ethanol and the suitable crystal was obtained by slow evaporation of the ethanol in a 10 mL vial with parafilm covered.

2 Experimental details

Hydrogen atoms attached to C atoms were placed geometrically and refined using a riding model approximation, with d(C–H) = 0.93 Å, 0.96 Å, or 0.97 Å(–CH, –CH3, –CH2). Uiso(H) = 1.2 Ueq(C) for CH or Uiso(H) = 1.5 Ueq(C) for CH3 and CH2 groups. 3 The ethyl group attached to O4 is positionally disordered and rotates around the O4. And it was split into two parts with 70 % and 30 %, respectively. The distance of O4–C14/O4–C14A and C15–C14/C15A–C14A was restricted to be identical by SADI command. RIGU command was used to restrict thermal ellipsoids to a reasonable extent. Interestingly, the ethyl group (C28–C29) of another molecule in the asymmetrical unit is ordered.

3 Comment

The 7-(dimethylamino)-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-ethyl carboxylate is a coumarin-containing fluorescent dye and has strong fluorescence emission in crystal state. Therefore, these coumarin based fluorescent dyes were developed in construction of fluorescent probe, bio-marker, solar cell, etc. 6 , 7 , 8 , 9 , 10 The crystal dye structure with a build in electron donor (dimethylamino) and electron acceptor (carbonyl and trifluoromethyl) constructed intramolecular electron push-pull system. With the specifically character of π system of coumarin, the emission behavior can be modified according to the requirement of material and device fabrication. In this case, the fluorescence emission maximum value can be shifted to longer wavelength smoothly. 11 , 12 , 13 Oled can be fabricated based on the highly efficient emiting dyes.

In the title crystal structure, the asymmetric unit contains two molecules. Both the bond lengths and the angles are in the expected ranges. The coumarin part in the dye structure is coplanar with the root mean square error (RMSD) in distance estimated to be 0.07 and 0.64 Å, respectively. Due to the nucleophilic addition of trifluoromethyl to the carbonyl, the hybridized sp2 C1 and C16 transformed to sp3 hybridization. Therefore, C1 and C16 are slightly twisted out of the coumarin plane. The distance of C2–C13 and C17–C27 are estimated to be 1.469 and 1.463 Å, which is shorter than the general saturated carbons. However, the carbonyl group (C13–O3 and C47–O7) twist from coumarin plane and the conjugation between the two parts disconnect. Vice versa, the distance of N1–C7 and N2–C22 are determined to be 1.364 and 1.366 Å, which is shorter than N1–C10/N1–C11 and N2–C24/N2–C25 (the distance ranging from 1.444 to 1.454 Å). It indicates that N1/N2 conjugates with the corresponding coumarin system, which facilitates the electron donation from N atom to coumarin part. Totally, the donor (NMe2) and the acceptor (carbonyl group), together with the coumarin moiety, jointly configured the intramolecular electron “push-pull” effect in a fluorescent dye system. Due to the electronic “push-pull” effect, one can effectively configure a modifiable fluorescent dye. 14 , 15 , 16 , 17 , 18 Furtherly, the structure of amino (N1/C7/C10/C11 and N2/C22/C24/C25) formed the planar rather than the trigonal pyramid geometry with the RMSD in distance 0.032 and 0.033 Å, respectively. It demonstrates the electron donation character of N1/N2. The adjacent parallel molecules are jointed by strong π⃛π interaction. The distance between the two parallel coumarin plane (C16/C17/C18/C19/C20/C21/C22/C23/C30/O5i1 and C16/C17/C18/C19/C20/C21/C22/C23/C30/O5i2 i1: −x, 1 − y, 1 − z; i2: −1 + x, y, z.) is determined to be 3.617 Å. The coumarin plane centroid distance is 3.784 Å and the parallel shift is 1.1 Å, corresponding to the parallel-displaced geometry. 19 Typical inter-/intramolecular C–H⃛O interactions are established. In the adjacent non-parallel molecules, four hydrogen bonds are observed (C5–H5⃛O1i3, C15A–H15E⃛O3i3, C20–H20⃛O5i4, C18–H18⃛O6i4, i3: −x, 2 − y, −z; i4: −1 + x, y, z.) with the C⃛O contacts ranging from 3.343 to 3.610 Å, C–H⃛O angle ranging from 162.5 to 172.6°. Also, there exists two intramolecular hydrogen bonds (O2–H2⃛O3i5, O6–H6A⃛O7i2, i5: 1 − x, 2 − y, −z) with the O⃛O contacts 2.698/2.651 Å and O–H⃛O 145.8/144.8°. The distances of C⃛O distances are well inside the interval of 3.0–4.0 Å and quoted by Desiraju. 20 And C–H⃛O angles are also in agreement with the above mentioned survey. 20 , 21 Additionally, the fluorine atom also involved in the hydrogen bond construction. The typical H⃛F contacts are C11–H11B⃛F5i6, C24–H24B⃛F1i6, and C14–H14B⃛F2i6 (i6: x, y, z). The H⃛F distance ranges from 3.435 to 3.545 Å. The hydrogen bonds configuration in the crystal is significant to understand the behavior of the fluorescent dyes. 22 , 23 , 24 , 25 , 26 Therefore, introduction of heteroatoms is beneficial to establish various inter- and/or intra-molecular hydrogen bonds, with which the radiative and nonradiative channels ratio is modifiable. 27 The stronger intramolecular interactions can quench the fluorescent emission of dye effectively. 28 , 29 , 30 , 31

In the crystal, the molecules were regularly packed by hydrogen bonds and π⃛π interactions. The driving force of parallel molecules packing is based on the π⃛π interaction mainly. While, the hydrogen bonds jointed the parallel molecules side by side. The weak interactions mentioned above determines its highly emissive character in solid state. 32 With no stronger T-shaped π⃛π interaction, a regular tight packing is avoided and thus ignite a highly fluorescent emission. 33 , 34 , 35 , 36 , 37 The nonradiative channel of excited dye molecules is inhibited to a large extent. 38 , 39 For 7-(dimethylamino)-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-ethyl carboxylate, the unique packing style, together with the intramolecular electron “push-pull” effect, leads to the unique emisson character in crystal state. 40 , 41 It shows that reasonable configuration of inter- and intra-molecular interaction based on heteroatoms and aromatic system is important in molecular designing. 42 , 43 , 44 In conclusion, the molecules are staggered layer by layer along with the axis b and c. The hydrogen bonds join the layers.

Corresponding author: Ruifeng Yue, School of Chemical Engineering, Henan Technical Institute, Zhengzhou, Henan, 450042 P.R. China, E-mail:

Acknowledgements

We also gratefully thank Prof. Xiaochuan Li (Henan Normal University) for lab facilities support, the single crystal X-ray diffraction data acquisition and structure solving.

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

  2. Research funding: Key Scientific and Technological Project of Henan Province (grant no. 222102230103).

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

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Received: 2024-12-01
Accepted: 2025-01-14
Published Online: 2025-01-27
Published in Print: 2025-04-28

© 2025 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. The crystal structure of N-(3-bromo-4-fluorophenyl)-N′-hydroxy-4-{[2-(4-methylphenyl)ethyl]amino}-1,2,5-oxadiazole-3-carboximidamide, C18H17BrFN5O2
  4. Synthesis and crystal structure of ethyl (2S,4aS,6aS,6bR,8aR,12aS,12bR,14bR,E)-10-(((3,4-dichlorobenzyl)oxy)imino)-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate
  5. The crystal structure of pyrazole nitrate
  6. Crystal structure of tetramethyl-bis(μ2-2-(2-hydroxy-3-methoxybenzylidene)-1-(6-(2-(2-hydroxy-3-methoxybenzylidene)hydrazine-1-carbonyl)picolinoyl)hydrazin-1-ido-κ4O,N,O′:O′)ditin(II) ─ ethanol (1/2), C54H62N10O14Sn2
  7. Crystal structure of catena-poly[μ3-iodido-(4-bromopyridine-κ1N)copper(I)], C5H4BrNCuI
  8. The crystal structure of cyclopentadienyl Co–P–C complexes by benzylideneacetone addition, C38H38CoO2P
  9. Synthesis and crystal structure of-(3S,10S,13S,17S)-N-(2-methoxyphenyl)-10,13-dimethyl-17-((R)-1-(phenylamino)ethyl)hexadecahydro-1H-cyclopenta[α]phenanthren-3-amine, C34H48N2O
  10. The crystal structure of (E)-3-((E)-3-(4-ethoxy-3-methoxyphenyl)-1-hydroxyallylidene) chroman-2,4-dione, C21H18O6
  11. The crystal structure of trans–L/D-[bis-(2-methyl-8-hydroxyquinoline-κ2 N,O) bis-(1,3,5-triaza-7-phosphaadamantane-κ2 P)cobalt(III)] tetrafluoroborate
  12. Crystal structure of 9-chloro-2,3,4,4a,5,6-hexahydro-1H-pyrido [1′,2′:1,6]pyrazino[2,3-b]quinoxaline, C14H15ClN4
  13. Crystal structure of 7-(diethylamino)-3-(benzoyl)-2 H -chromen-2-one, C20H19NO3
  14. The crystal structure of 4–bromo-3,5-dinitropyrazole
  15. Crystal structure of 8-hydroxy-3,5,8a-trimethyl-7,8,8a,9-tetrahydronaphtho[2,3-b]furan-4,6-dione, C15H16O4
  16. Crystal structure of 5-hydroxy-3,5,8a-trimethyl-4a,5,6,7,8a,9-hexahydronaphtho[2,3-b]furan-4,8-dione, C15H18O4
  17. Synthesis and crystal structure of-(3S,10S,13S,17S)-N-(2-methoxyphenyl)-10,13-dimethyl-17-((R)-1-(p-tolylamino)ethyl)hexadecahydro-1H-cyclopenta[α]phenanthren-3-amine, C35H50N2O
  18. The crystal structure of catena-poly((μ2-1,3,5-tri(1H- imidazol-1-yl)benzene κ2N:N′)-bis(4-hydroxbenzoato-κ1O)-zinc(II) monohydrate), C29H24N6O7Zn
  19. Crystal structure of 2-(benzo[d]oxazol-2-yl)acetonitrile, C9H6N2O
  20. Crystal structure of 1,3-dihydroxy-6,8-dimethoxy-2-(6-methyltetrahydro-2Hpyran-2-yl)-4a,9a-dihydroanthracene-9,10-dione, C22H22O7
  21. The crystal structure of the double salt potassium 1-methylpiperazine-1,4-di-ium trinitrate, C5H14KN5O9
  22. Crystal structure of 5′-hydroxy-6′-methoxy-1′-methyl-2′,3′,8′,8a′-tetrahydro-1′H-spiro[cyclohexane-1,7′-cyclopenta[ij]isoquinoline]-2,5-dien-4-one, C18H19NO3
  23. The crystal structure of 1,1′-(2,3,5,6-tetramethylpyrazine-1,4-diyl)bis(ethan-1-one), C12H18N2O2
  24. Crystal structure of [μ2-piperazine-1,4-bis(2-hydroxypropanesulfonato-κ2O:O′)] bis(μ2-4,4′-trimethylenedipyridyl-κ2N:N′)disilver(I), C18H24AgN3O4S
  25. Crystal structure of bis ((1-((E)-((4-methoxyphenyl)imino)methyl)naphthalen-2-yl)oxy) copper(II), C36H28CuN2O4
  26. Synthesis and crystal structure of 6,6′-((1E,11E)-5,8-dioxa-2,11-diazadodeca-1,11-diene-1,12-diyl) bis(2,4-di-tert-butylphenol), C36H56N2O4
  27. The crystal structure of barium hexahydroxidoiridate(IV) dihydroxide, Ba2[Ir(OH)6](OH)2
  28. Crystal structure of cinnamoyl ferrocene, C19H16FeO
  29. Crystal structure of (E)-3-(4-butoxyphenyl)acryloylferrocene, C23H24FeO2
  30. Crystal structure of 7-(dimethylamino)-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-ethyl carboxylate, C15H16F3NO4
  31. The crystal structure of 1-phenylethan-1-aminium 4-hydroxy-3,5-dimethoxybenzoate C17H21NO5
  32. The crystal structure of 1,3,5-trichloro-2-nitrobenzene
  33. The crystal structure of tris(μ2-bromido)-bis(η6-p-cymene)-diosmium(II) tetrafluoroborate, C20H28BBr3F4Os2
  34. Crystal structure of new barium lithium manganese fluorides: Ba14Li1.87Mn14.13F68 with a Jarlite–related structure
  35. Crystal structure of (4-fluorobenzyl)triphenylphosphonium chloride, C25H21ClFP
  36. The crystal structure of calcitriol–chloroform (1/1), C27H44O3⋅CHCl3
  37. The crystal structure of (E)-1-((3)-nitrophenyl)pyren-3-(pyren-1-yl)prop-2-en-1-one, C25H15NO3
  38. Crystal structure of (E)-2-hydroxy-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H16N2O3
  39. Crystal structure of (E)-(3-(thiophen-2-yl)acryloyl)ferrocene, C17H14FeOS
  40. Crystal structure of (E)-(3-(furan-2-yl)acryloyl)ferrocene, C17H14FeO2
  41. Synthesis and crystal structure poly[diaqua(μ3-3-(((7-hydroxy-3-(4-methoxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl) methyl)ammonio)propanoate-κ3 O:O′:O″) sodium(I)] monohydrate, C20H24NNaO12S
  42. Crystal structure of 9-methoxy-4-(2-methoxypyridin-3-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine C19H18N4O2
  43. Synthesis and crystal structure of 4-(difluoromethyl)-1-methyl-N-(pyridin-3-yl)-1H-pyrazole-3-carboxamide hydrate, C11H12F2N4O2
  44. The crystal structure of caesalfurfuric acid B, C22H32O4
  45. The crystal structure of 2-bromo-2-(5-bromo-2-methyl-4-nitro-1H-imidazol-1-yl)-1-phenylethanone, C12H9Br2N3O3
  46. The crystal structure of bis{chlorido-[μ2-(1-oxidopyridin-2-yl)(pyridin-2-yl)amido-κ3 O,N, N′]copper(II)}, C20H16Cl2Cu2N6O2
  47. The crystal structure of 3-amino-2-formyl-1-phenyl-9,10-dihydrophenanthrene-4-carbonitrile, C22H16N2O
  48. The crystal structure of 1,1′-(2,5-dimethylpyrazine-1,4-diyl)bis(ethan-1-one), C10H14N2O2
  49. Crystal structure of 5′-(9-phenyl-9H-carbazol-3-yl)-[2,2′-bithiophene]-5-carbaldehyde, C27H17NOS2
  50. The crystal structure of the double salt dipyridin-1-ium bromide tribromide
  51. Crystal structure of (E)-(3-(3-methylthiophen-2-yl)acryloyl)ferrocene, C18H16FeOS
  52. Crystal structure of (E)-(3-(4-phenoxyphenyl)acryloyl)ferrocene, C25H20FeO2
  53. Crystal structure of (E)-(3-(3,4-dimethylphenyl)acryloyl)ferrocene, C21H20FeO
  54. Crystal structure of [(1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N‴)tetracyanidodiplatinum(II)] dimethyl sulfoxide solvate, C18H36N8O2Pt2S2
  55. Crystal structure of (4-ethoxybenzyl)triphenylphosphonium bromide ethanol solvate, C29H32BrO2P
  56. Crystal structure of (1-naphthalen-1-yl-methyl)triphenylphosphonium chloride ethanol solvate, C31H30ClOP
  57. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)platinum(II) bis[tribromido(dimethyl sulfoxide-κS)platinate(II)], C14H36Br6N4O2Pt3S2
  58. Crystal structure of (2-methylbenzyl)triphenylphosphonium chloride ethanol solvate, C28H30ClOP
  59. Crystal structure of bis(η2, σ1-8-methoxycyclooct-4-enyl)(μ2-1,4,8,11-tetraazacyclotetradecane-κ4 N, N′, N″, N‴)diplatinum(II) dibromide, C28H54Br2N4O2Pt2
  60. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) tetrabromidopalladate(II), C10H24Br4N4Pd2
  61. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) bis[trichlorido(dimethyl sulfoxide-κS)platinate(II)], C14H36Cl6N4O2PdPt2S2
  62. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) tetraiodidopalladate(II), C10H24I4N4Pd2
https://doi.org/10.1515/ncrs-2024-0460
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Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of N-(3-bromo-4-fluorophenyl)-N′-hydroxy-4-{[2-(4-methylphenyl)ethyl]amino}-1,2,5-oxadiazole-3-carboximidamide, C18H17BrFN5O2
  4. Synthesis and crystal structure of ethyl (2S,4aS,6aS,6bR,8aR,12aS,12bR,14bR,E)-10-(((3,4-dichlorobenzyl)oxy)imino)-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate
  5. The crystal structure of pyrazole nitrate
  6. Crystal structure of tetramethyl-bis(μ2-2-(2-hydroxy-3-methoxybenzylidene)-1-(6-(2-(2-hydroxy-3-methoxybenzylidene)hydrazine-1-carbonyl)picolinoyl)hydrazin-1-ido-κ4O,N,O′:O′)ditin(II) ─ ethanol (1/2), C54H62N10O14Sn2
  7. Crystal structure of catena-poly[μ3-iodido-(4-bromopyridine-κ1N)copper(I)], C5H4BrNCuI
  8. The crystal structure of cyclopentadienyl Co–P–C complexes by benzylideneacetone addition, C38H38CoO2P
  9. Synthesis and crystal structure of-(3S,10S,13S,17S)-N-(2-methoxyphenyl)-10,13-dimethyl-17-((R)-1-(phenylamino)ethyl)hexadecahydro-1H-cyclopenta[α]phenanthren-3-amine, C34H48N2O
  10. The crystal structure of (E)-3-((E)-3-(4-ethoxy-3-methoxyphenyl)-1-hydroxyallylidene) chroman-2,4-dione, C21H18O6
  11. The crystal structure of trans–L/D-[bis-(2-methyl-8-hydroxyquinoline-κ2 N,O) bis-(1,3,5-triaza-7-phosphaadamantane-κ2 P)cobalt(III)] tetrafluoroborate
  12. Crystal structure of 9-chloro-2,3,4,4a,5,6-hexahydro-1H-pyrido [1′,2′:1,6]pyrazino[2,3-b]quinoxaline, C14H15ClN4
  13. Crystal structure of 7-(diethylamino)-3-(benzoyl)-2 H -chromen-2-one, C20H19NO3
  14. The crystal structure of 4–bromo-3,5-dinitropyrazole
  15. Crystal structure of 8-hydroxy-3,5,8a-trimethyl-7,8,8a,9-tetrahydronaphtho[2,3-b]furan-4,6-dione, C15H16O4
  16. Crystal structure of 5-hydroxy-3,5,8a-trimethyl-4a,5,6,7,8a,9-hexahydronaphtho[2,3-b]furan-4,8-dione, C15H18O4
  17. Synthesis and crystal structure of-(3S,10S,13S,17S)-N-(2-methoxyphenyl)-10,13-dimethyl-17-((R)-1-(p-tolylamino)ethyl)hexadecahydro-1H-cyclopenta[α]phenanthren-3-amine, C35H50N2O
  18. The crystal structure of catena-poly((μ2-1,3,5-tri(1H- imidazol-1-yl)benzene κ2N:N′)-bis(4-hydroxbenzoato-κ1O)-zinc(II) monohydrate), C29H24N6O7Zn
  19. Crystal structure of 2-(benzo[d]oxazol-2-yl)acetonitrile, C9H6N2O
  20. Crystal structure of 1,3-dihydroxy-6,8-dimethoxy-2-(6-methyltetrahydro-2Hpyran-2-yl)-4a,9a-dihydroanthracene-9,10-dione, C22H22O7
  21. The crystal structure of the double salt potassium 1-methylpiperazine-1,4-di-ium trinitrate, C5H14KN5O9
  22. Crystal structure of 5′-hydroxy-6′-methoxy-1′-methyl-2′,3′,8′,8a′-tetrahydro-1′H-spiro[cyclohexane-1,7′-cyclopenta[ij]isoquinoline]-2,5-dien-4-one, C18H19NO3
  23. The crystal structure of 1,1′-(2,3,5,6-tetramethylpyrazine-1,4-diyl)bis(ethan-1-one), C12H18N2O2
  24. Crystal structure of [μ2-piperazine-1,4-bis(2-hydroxypropanesulfonato-κ2O:O′)] bis(μ2-4,4′-trimethylenedipyridyl-κ2N:N′)disilver(I), C18H24AgN3O4S
  25. Crystal structure of bis ((1-((E)-((4-methoxyphenyl)imino)methyl)naphthalen-2-yl)oxy) copper(II), C36H28CuN2O4
  26. Synthesis and crystal structure of 6,6′-((1E,11E)-5,8-dioxa-2,11-diazadodeca-1,11-diene-1,12-diyl) bis(2,4-di-tert-butylphenol), C36H56N2O4
  27. The crystal structure of barium hexahydroxidoiridate(IV) dihydroxide, Ba2[Ir(OH)6](OH)2
  28. Crystal structure of cinnamoyl ferrocene, C19H16FeO
  29. Crystal structure of (E)-3-(4-butoxyphenyl)acryloylferrocene, C23H24FeO2
  30. Crystal structure of 7-(dimethylamino)-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-ethyl carboxylate, C15H16F3NO4
  31. The crystal structure of 1-phenylethan-1-aminium 4-hydroxy-3,5-dimethoxybenzoate C17H21NO5
  32. The crystal structure of 1,3,5-trichloro-2-nitrobenzene
  33. The crystal structure of tris(μ2-bromido)-bis(η6-p-cymene)-diosmium(II) tetrafluoroborate, C20H28BBr3F4Os2
  34. Crystal structure of new barium lithium manganese fluorides: Ba14Li1.87Mn14.13F68 with a Jarlite–related structure
  35. Crystal structure of (4-fluorobenzyl)triphenylphosphonium chloride, C25H21ClFP
  36. The crystal structure of calcitriol–chloroform (1/1), C27H44O3⋅CHCl3
  37. The crystal structure of (E)-1-((3)-nitrophenyl)pyren-3-(pyren-1-yl)prop-2-en-1-one, C25H15NO3
  38. Crystal structure of (E)-2-hydroxy-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H16N2O3
  39. Crystal structure of (E)-(3-(thiophen-2-yl)acryloyl)ferrocene, C17H14FeOS
  40. Crystal structure of (E)-(3-(furan-2-yl)acryloyl)ferrocene, C17H14FeO2
  41. Synthesis and crystal structure poly[diaqua(μ3-3-(((7-hydroxy-3-(4-methoxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl) methyl)ammonio)propanoate-κ3 O:O′:O″) sodium(I)] monohydrate, C20H24NNaO12S
  42. Crystal structure of 9-methoxy-4-(2-methoxypyridin-3-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine C19H18N4O2
  43. Synthesis and crystal structure of 4-(difluoromethyl)-1-methyl-N-(pyridin-3-yl)-1H-pyrazole-3-carboxamide hydrate, C11H12F2N4O2
  44. The crystal structure of caesalfurfuric acid B, C22H32O4
  45. The crystal structure of 2-bromo-2-(5-bromo-2-methyl-4-nitro-1H-imidazol-1-yl)-1-phenylethanone, C12H9Br2N3O3
  46. The crystal structure of bis{chlorido-[μ2-(1-oxidopyridin-2-yl)(pyridin-2-yl)amido-κ3 O,N, N′]copper(II)}, C20H16Cl2Cu2N6O2
  47. The crystal structure of 3-amino-2-formyl-1-phenyl-9,10-dihydrophenanthrene-4-carbonitrile, C22H16N2O
  48. The crystal structure of 1,1′-(2,5-dimethylpyrazine-1,4-diyl)bis(ethan-1-one), C10H14N2O2
  49. Crystal structure of 5′-(9-phenyl-9H-carbazol-3-yl)-[2,2′-bithiophene]-5-carbaldehyde, C27H17NOS2
  50. The crystal structure of the double salt dipyridin-1-ium bromide tribromide
  51. Crystal structure of (E)-(3-(3-methylthiophen-2-yl)acryloyl)ferrocene, C18H16FeOS
  52. Crystal structure of (E)-(3-(4-phenoxyphenyl)acryloyl)ferrocene, C25H20FeO2
  53. Crystal structure of (E)-(3-(3,4-dimethylphenyl)acryloyl)ferrocene, C21H20FeO
  54. Crystal structure of [(1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N‴)tetracyanidodiplatinum(II)] dimethyl sulfoxide solvate, C18H36N8O2Pt2S2
  55. Crystal structure of (4-ethoxybenzyl)triphenylphosphonium bromide ethanol solvate, C29H32BrO2P
  56. Crystal structure of (1-naphthalen-1-yl-methyl)triphenylphosphonium chloride ethanol solvate, C31H30ClOP
  57. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)platinum(II) bis[tribromido(dimethyl sulfoxide-κS)platinate(II)], C14H36Br6N4O2Pt3S2
  58. Crystal structure of (2-methylbenzyl)triphenylphosphonium chloride ethanol solvate, C28H30ClOP
  59. Crystal structure of bis(η2, σ1-8-methoxycyclooct-4-enyl)(μ2-1,4,8,11-tetraazacyclotetradecane-κ4 N, N′, N″, N‴)diplatinum(II) dibromide, C28H54Br2N4O2Pt2
  60. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) tetrabromidopalladate(II), C10H24Br4N4Pd2
  61. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) bis[trichlorido(dimethyl sulfoxide-κS)platinate(II)], C14H36Cl6N4O2PdPt2S2
  62. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) tetraiodidopalladate(II), C10H24I4N4Pd2
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Heruntergeladen am 3.10.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2024-0460/html
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