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The crystal structure of (E)-3-chloro-2-(2-(4-fluorobenzylidene)hydrazinyl)pyridine, C12H9ClFN3

  • Bin-Yu Zheng , Na-Bo Sun ORCID logo EMAIL logo , Xue-Song Chen and Xing-Hai Liu
Published/Copyright: March 1, 2022
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 237 Issue 3

Abstract

C12H9ClFN3, monoclinic, P21/n (no. 14), a = 10.120(4) Å, b = 13.823(6) Å, c = 16.480(7) Å, β = 91.744(8)°, V = 2304.4(17) Å3, Z = 8, R gt (F) = 0.0402, wR ref (F 2) = 0.0932, T = 113.15 K.

CCDC no.: 2149847

Only one of the two crystallographically independent moleules of the title 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: Colorless prism
Size: 0.20 × 0.20 × 0.20 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.32 mm−1
Diffractometer, scan mode: ω
θ max, completeness: 27.8°, >99%
N(hkl)measured, N(hkl)unique, R int: 22,536, 5483, 0.044
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 4604
N(param)refined: 307
Programs: Olex2 [1], SHELX [2, 3]
Table 2:

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

Atom x y z U iso*/U eq
Cl1 −0.38845 (4) −0.19073 (3) 0.08628 (3) 0.03236 (12)
F1 0.20724 (9) 0.40525 (6) 0.24092 (6) 0.0338 (2)
N1 −0.22853 (13) 0.08362 (8) 0.17193 (8) 0.0222 (3)
N2 −0.29329 (13) −0.00277 (8) 0.15728 (8) 0.0245 (3)
H2 −0.2525 −0.0582 0.1662 0.029*
N3 −0.49118 (13) 0.08102 (8) 0.13412 (8) 0.0233 (3)
C1 0.12947 (15) 0.32514 (10) 0.23167 (10) 0.0234 (3)
C2 −0.00248 (16) 0.33696 (11) 0.21119 (11) 0.0279 (4)
H2A −0.0389 0.3998 0.2036 0.033*
C3 −0.08082 (15) 0.25556 (10) 0.20191 (10) 0.0261 (4)
H3 −0.1722 0.2627 0.1882 0.031*
C4 −0.02774 (14) 0.16277 (10) 0.21239 (9) 0.0198 (3)
C5 0.10637 (15) 0.15427 (11) 0.23368 (10) 0.0251 (3)
H5 0.1440 0.0919 0.2415 0.030*
C6 0.18574 (15) 0.23591 (11) 0.24358 (10) 0.0281 (4)
H6 0.2769 0.2299 0.2583 0.034*
C7 −0.10802 (15) 0.07601 (10) 0.19870 (10) 0.0221 (3)
H7 −0.0713 0.0139 0.2096 0.026*
C8 −0.42223 (15) −0.00121 (10) 0.12863 (9) 0.0210 (3)
C9 −0.48146 (16) −0.08549 (10) 0.09531 (10) 0.0243 (3)
C10 −0.61163 (16) −0.08396 (11) 0.06917 (10) 0.0291 (4)
H10 −0.6525 −0.1405 0.0474 0.035*
C11 −0.68249 (16) 0.00173 (11) 0.07515 (10) 0.0303 (4)
H11 −0.7727 0.0053 0.0577 0.036*
C12 −0.61782 (16) 0.08122 (11) 0.10706 (10) 0.0274 (4)
H12 −0.6658 0.1401 0.1102 0.033*
Cl2 0.05702 (4) 0.58235 (2) 0.16911 (2) 0.02695 (11)
F2 −0.23767 (11) 1.13806 (7) 0.56619 (6) 0.0448 (3)
N4 −0.09219 (12) 0.83511 (8) 0.29660 (8) 0.0208 (3)
N5 −0.05299 (12) 0.75652 (8) 0.25234 (8) 0.0219 (3)
H5A −0.0418 0.6997 0.2756 0.026*
N6 −0.06113 (13) 0.85439 (8) 0.13699 (8) 0.0257 (3)
C13 −0.20850 (16) 1.05980 (11) 0.51954 (11) 0.0288 (4)
C14 −0.23277 (15) 1.06506 (11) 0.43733 (11) 0.0275 (4)
H14 −0.2710 1.1216 0.4137 0.033*
C15 −0.20081 (14) 0.98696 (10) 0.38954 (10) 0.0236 (3)
H15 −0.2186 0.9893 0.3326 0.028*
C16 −0.14204 (14) 0.90391 (10) 0.42449 (10) 0.0212 (3)
C17 −0.12203 (15) 0.90098 (10) 0.50860 (10) 0.0248 (3)
H17 −0.0854 0.8445 0.5332 0.030*
C18 −0.15470 (15) 0.97917 (11) 0.55715 (10) 0.0281 (4)
H18 −0.1404 0.9771 0.6144 0.034*
C19 −0.09868 (15) 0.82341 (10) 0.37355 (10) 0.0222 (3)
H19 −0.0756 0.7630 0.3975 0.027*
C20 −0.03169 (14) 0.76864 (10) 0.17111 (10) 0.0205 (3)
C21 0.02210 (14) 0.69337 (10) 0.12411 (10) 0.0219 (3)
C22 0.04700 (16) 0.70789 (12) 0.04390 (10) 0.0307 (4)
H22 0.0824 0.6573 0.0121 0.037*
C23 0.01954 (19) 0.79819 (12) 0.00960 (11) 0.0384 (4)
H23 0.0375 0.8116 −0.0455 0.046*
C24 −0.03450 (17) 0.86693 (12) 0.05883 (11) 0.0344 (4)
H24 −0.0545 0.9282 0.0354 0.041*

Source of material

According to the our previous work [4], the 3-chloro-2-hydrazinylpyridine (1.43 g, 0.1 mol) and 4-fluoro-benzaldehyde (1.24 g, 0.1 mol) was dissolved in EtOH (50 mL) and stirred at room temperature for 24 h. Then a solid was obtained, which was filtered and dried with 85% yield. The solid was recrystallized from ethanol as colorless block crystals.

Experimental details

Hydrogen atoms were added using riding models. Their U iso values were set to 1.2U eq of the parent atoms. Using Olex2 [1], the structure was solved with the ShelXS [2] structure solution program and refined with the ShelXL [3] refinement package.

Comment

Pyridine is an attractive heterocycle because of the excellent biological activity of some derivatives, such as insecticidal activity [5], fungicidal activity [6], herbicidal activity [7]. On the other hand, the hydrazone group is an active group in many bioactive molecules [8].

The asymmetric unit of the title pyridine compound consists of two molecule, which is the same as reported work [4, 9]. Geometric parameters (bond lengths and bond angles) are all in the normal ranges [10], [11], [12]. The title compound shows an E configuration around the C7=N1 bond. The C7=N1 and N4=C19 bond lengths (1.289(2), 1.282(2) Å) are typical for a C=N double bond [13]. In the title compound, the phenyl ring is nearly in the same plane with the pyridine ring in both independent molecules.

Corresponding author: Na-Bo Sun, College of Biology and Environmental Engineering, Zhejiang Shuren University, Hangzhou 310015, China, E-mail:

Funding source: Zhejiang Shuren University Basic Scientific Research Special Funds

Award Identifier / Grant number: 2020XZ011

Funding source: Chemical Company for Research

Award Identifier / Grant number: KYY-HX-20210140

Award Identifier / Grant number: KYY-HX-20190720

  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 Zhejiang Shuren University Basic Scientific Research Special Funds (No. 2020XZ011), the Chemical Company for Research (KYY-HX-20210140, KYY-HX-20190720).

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

References

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Received: 2021-12-29
Accepted: 2022-02-03
Published Online: 2022-03-01
Published in Print: 2022-06-27

© 2022 Bin-Yu Zheng et al., published by De Gruyter, Berlin/Boston

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

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of (E)-(4-imidazol-1-yl-phenyl)-(2-methoxy-benzylidene)-amine monohydrate, C17H17N3O2
  4. Crystal structure of 6-methyl-3-(pyrrolidine-1-carbonyl)-2H-chromen-2-one, C15H15N1O3
  5. Crystal structure of 4-methyl-4-nitropentanoic acid, C6H11NO4
  6. The crystal structure of (E)-3-(furan-2-yl)acrylonitrile, C7H5NO
  7. Crystal structure of 3-(difluoromethyl)-1-methyl-N-(4,11,11-trimethyl-1,2,3,4-tetrahydro-1,4-methanoacridin-9-yl)-1H-pyrazole-4-carboxamide monohydrate, C23H26F2N4O3
  8. Crystal structure of 2-(4-bromobenzyloxy)-6-chloropyridine, C12H9BrClNO
  9. Crystal structure of N-(4-bromo-2,6-dichloro-phenyl)pyrazin-2-amine, C10H6BrCl2N3
  10. Crystal structure of (E)-1-(2–nitrophenyl)-3-phenylprop-2-en-1-one, C15H11NO3
  11. The crystal structure of (E)-3-chloro-2-(2-(4-fluorobenzylidene)hydrazinyl)pyridine, C12H9ClFN3
  12. Crystal structure of (E)-amino(2-(thiazol-2-ylmethylene)hydrazineyl)methaniminium nitrate, C10H16N12O6S2
  13. Crystal structure of 9-methoxy-2,3,4,4a,5,6-hexahydro-1H-pyrido [1′,2′:1,6]pyrazino[2,3-b]quinoxaline, C15H18N4O
  14. The crystal structure bis(dimethylsulfoxide-κ1O)-dipyridine-κ1 N-bis(m2-(Z)-3-methyl-2-oxido-N-((Z)-oxido(phenyl)methylene)benzohydrazonato-κ5)trinickel(II) - dimethylsulfoxide (1/2), C48H56N6Ni3O10S4
  15. Crystal structure of bis(bis(triphenylphosphine)iminium) tetradecacarbonyltetratelluridopentaferrate(2-), (PPN)2[Fe5Te4(CO)14]
  16. Crystal structure of 4-Hydroxy-3-(naphthalen-2-ylthio)pent-3-en-2-one, C15H14O2S
  17. The crystal structure of [(1,10-phenanthroline-κ2 N,N)-bis(6-phenylpyridine-2-carboxylate-κ2 N,O)nickel(II)] monohydrate, C36H26N4O5Ni
  18. Crystal structure of 3,3′-(pyridine-2,6-diylbis(methylene))bis(1-propyl-1H-imidazol-3-ium) ditetrafluoroborate, C19H27B2F8N5
  19. The crystal structure of (E)-1-(4-aminophenyl)-3-(p-tolyl)prop-2-en-1-one, C16H15NO
  20. The crystal structure of poly[(μ2-terephthalato-κ4O,O′: O″,O‴)-(μ4-terephthalato-κ4O:O′:O″:O‴)-{μ4-(1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ4O:O′:O″,O‴)}dicadmium(II)] – water – acetronitrile (1/2/2), C38H36N14O10Cd2
  21. The crystal structure of diaqua-bis(6-phenylpyridine-2-carboxylato-κ2 N,O)cobalt(II)–water–N,N-dimethylformamide(1/2/1), C27H31N3O9Co
  22. The co-crystal structure of 4-hydroxy-3-methoxybenzoic acid – 4,4′-bipyridine, C8H8O4·C10H8N2
  23. Crystal structure of catena-poly[(μ2-1,1′-(biphenyl-4,4′-diyl)bis(1H-imidazol)-κ2N:N′)-bis(4-bromobenzoate-κ1O)cobalt(II)], C32H22Br2CoN4O4
  24. Crystal structure of (E)-5-propyl-4-((pyridin-2-ylmethylene)amino)-2,4-dihydro-3H-1,2,4-triazole-3-thione – methanol (1/1), C11H13N5S
  25. The crystal structure of (Z)-4-bromo-6-(((1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl)amino)methylene)cyclohexa-2,4-dien-1-one monohydrate, C11H16BrNO5
  26. Crystal structure of bis(tetrapropylammonium) nonaselenidotetrastannate(IV), (Pr4N)2[Sn4Se9]
  27. Crystal structure of 2,6-di-tert-butyl-4-(4-chlorobenzylidene)cyclohexa-2,5-dien-1-one, C21H25ClO
  28. Crystal structure of (2,2′-((naphthalen-1-ylmethyl)azanediyl)diacetato-κ3 N,O,O′)-(1,10-phenanthroline-κ2 N,N′)-copper(II) trihydrate, CuC27H27N3O7
  29. The crystal structure of tetrakis(6-phenylpyridine-2-carboxylato-κ2N,O)-bis(1H-pyrazol-3-ylamine-κ2 N:N)dicobalt(II) dihydrate, C27H23N5O5Co
  30. The crystal structure of bis((E)-2-((tert-butylimino)methyl)-4-chlorophenolato-κ2N,O)zinc(II), C22H26Cl2N2O2Zn
  31. The crystal structure of poly[diaqua-(μ3-5-nitrobenzene-1,2,3-tricarboxylato-κ3O:O′:O′)-(μ2-4,4′-dipyridylamine-κ2N:N′)copper(II)], C38H30Cu3N8O20
  32. The crystal structure of (E)-1-ferrocenyl-3-(naphthalen-1-yl)prop-2-en-1-one, C23H18FeO
  33. The crystal structure of (E)-1-ferrocenyl-3-(4-isopropylphenyl)prop-2-en-1-one, C22H22FeO
  34. Crystal structure of 6-hydroxy-2,2-dimethyl-4Hbenzo[d][1,3]dioxin-4-one, C10H10O4
  35. The crystal structure of (2E,4E)-1-ferrocenyl-5-phenylpenta-2,4-dien-1-one, C21H18FeO
  36. Crystal structure of alaninato-κ2N,O-bis(hydroxylamido-κ2N,O)-oxido-vanadium(V), C3H10N3O5V
  37. Crystal structure of catena-poly[aqua-bis[μ2-6-(1H-imidazol-1-yl)nicotinato-κ2 N,O]copper(II)], C18H14N6O5Cu
  38. Crystal structure of diethyl 4,6-diphenyl-1,9-di-p-tolylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta[b]pyridine-3,5(2H)-dicarboxylate, C42H42N2O4
  39. The crystal structure of cobalt cadmium bis(hydrogenphosphate) bis(phosphate(V)) tetrahydrate, H10O20P4Co3.14Cd1.86
  40. Crystal structure of dimethyl 1,4,6,9-tetraphenylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta[b]pyridine-3,7(2H)-dicarboxylate, C38H34N2O4
  41. Crystal structure of (Z)-4-(furan-2-yl((4-iodophenyl)amino)methylene)-5-methyl-2(p-tolyl)-2,4-dihydro-3H-pyrazol-3-one, C21H16I N3O2
  42. Crystal structure of (E)-1-(4-(3,5-dimethoxystyryl)phenyl)-7-ethylheptanedioate, C25H30O6
  43. Crystal structure of 6-bromo-2-(4-chlorophenyl)chroman-4-one (6-bromo-4′-chloroflavanone), C15H10BrClO2
  44. The crystal structure of 2-(benzhydryloxy)-3-nitropyridine, C18H14N2O3
  45. The crystal structure of 1,3(4,1)-dipyridin-1-iuma-2(1,8)-diethynylanthracena-5(1,3)-benzenacyclohexaphane-11,31-diium bis(hexafluoridophosphate), C36H24F12N2P2
  46. Crystal structure of 3,6-di-tert-butyl-1-iodo-9-methyl-8-(pyren-1-ylethynyl)-9H-carbazole, C39H34IN
  47. The cocrystal 2-(dimethylammonio)-5-nitrobenzoate – 2-(dimethylamino)-5-nitrobenzoic acid, C9H10N2O4
  48. Crystal structure of 5-nitroquinazolin-4(3H)-one, C8H5N3O3
https://doi.org/10.1515/ncrs-2021-0489
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of (E)-(4-imidazol-1-yl-phenyl)-(2-methoxy-benzylidene)-amine monohydrate, C17H17N3O2
  4. Crystal structure of 6-methyl-3-(pyrrolidine-1-carbonyl)-2H-chromen-2-one, C15H15N1O3
  5. Crystal structure of 4-methyl-4-nitropentanoic acid, C6H11NO4
  6. The crystal structure of (E)-3-(furan-2-yl)acrylonitrile, C7H5NO
  7. Crystal structure of 3-(difluoromethyl)-1-methyl-N-(4,11,11-trimethyl-1,2,3,4-tetrahydro-1,4-methanoacridin-9-yl)-1H-pyrazole-4-carboxamide monohydrate, C23H26F2N4O3
  8. Crystal structure of 2-(4-bromobenzyloxy)-6-chloropyridine, C12H9BrClNO
  9. Crystal structure of N-(4-bromo-2,6-dichloro-phenyl)pyrazin-2-amine, C10H6BrCl2N3
  10. Crystal structure of (E)-1-(2–nitrophenyl)-3-phenylprop-2-en-1-one, C15H11NO3
  11. The crystal structure of (E)-3-chloro-2-(2-(4-fluorobenzylidene)hydrazinyl)pyridine, C12H9ClFN3
  12. Crystal structure of (E)-amino(2-(thiazol-2-ylmethylene)hydrazineyl)methaniminium nitrate, C10H16N12O6S2
  13. Crystal structure of 9-methoxy-2,3,4,4a,5,6-hexahydro-1H-pyrido [1′,2′:1,6]pyrazino[2,3-b]quinoxaline, C15H18N4O
  14. The crystal structure bis(dimethylsulfoxide-κ1O)-dipyridine-κ1 N-bis(m2-(Z)-3-methyl-2-oxido-N-((Z)-oxido(phenyl)methylene)benzohydrazonato-κ5)trinickel(II) - dimethylsulfoxide (1/2), C48H56N6Ni3O10S4
  15. Crystal structure of bis(bis(triphenylphosphine)iminium) tetradecacarbonyltetratelluridopentaferrate(2-), (PPN)2[Fe5Te4(CO)14]
  16. Crystal structure of 4-Hydroxy-3-(naphthalen-2-ylthio)pent-3-en-2-one, C15H14O2S
  17. The crystal structure of [(1,10-phenanthroline-κ2 N,N)-bis(6-phenylpyridine-2-carboxylate-κ2 N,O)nickel(II)] monohydrate, C36H26N4O5Ni
  18. Crystal structure of 3,3′-(pyridine-2,6-diylbis(methylene))bis(1-propyl-1H-imidazol-3-ium) ditetrafluoroborate, C19H27B2F8N5
  19. The crystal structure of (E)-1-(4-aminophenyl)-3-(p-tolyl)prop-2-en-1-one, C16H15NO
  20. The crystal structure of poly[(μ2-terephthalato-κ4O,O′: O″,O‴)-(μ4-terephthalato-κ4O:O′:O″:O‴)-{μ4-(1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ4O:O′:O″,O‴)}dicadmium(II)] – water – acetronitrile (1/2/2), C38H36N14O10Cd2
  21. The crystal structure of diaqua-bis(6-phenylpyridine-2-carboxylato-κ2 N,O)cobalt(II)–water–N,N-dimethylformamide(1/2/1), C27H31N3O9Co
  22. The co-crystal structure of 4-hydroxy-3-methoxybenzoic acid – 4,4′-bipyridine, C8H8O4·C10H8N2
  23. Crystal structure of catena-poly[(μ2-1,1′-(biphenyl-4,4′-diyl)bis(1H-imidazol)-κ2N:N′)-bis(4-bromobenzoate-κ1O)cobalt(II)], C32H22Br2CoN4O4
  24. Crystal structure of (E)-5-propyl-4-((pyridin-2-ylmethylene)amino)-2,4-dihydro-3H-1,2,4-triazole-3-thione – methanol (1/1), C11H13N5S
  25. The crystal structure of (Z)-4-bromo-6-(((1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl)amino)methylene)cyclohexa-2,4-dien-1-one monohydrate, C11H16BrNO5
  26. Crystal structure of bis(tetrapropylammonium) nonaselenidotetrastannate(IV), (Pr4N)2[Sn4Se9]
  27. Crystal structure of 2,6-di-tert-butyl-4-(4-chlorobenzylidene)cyclohexa-2,5-dien-1-one, C21H25ClO
  28. Crystal structure of (2,2′-((naphthalen-1-ylmethyl)azanediyl)diacetato-κ3 N,O,O′)-(1,10-phenanthroline-κ2 N,N′)-copper(II) trihydrate, CuC27H27N3O7
  29. The crystal structure of tetrakis(6-phenylpyridine-2-carboxylato-κ2N,O)-bis(1H-pyrazol-3-ylamine-κ2 N:N)dicobalt(II) dihydrate, C27H23N5O5Co
  30. The crystal structure of bis((E)-2-((tert-butylimino)methyl)-4-chlorophenolato-κ2N,O)zinc(II), C22H26Cl2N2O2Zn
  31. The crystal structure of poly[diaqua-(μ3-5-nitrobenzene-1,2,3-tricarboxylato-κ3O:O′:O′)-(μ2-4,4′-dipyridylamine-κ2N:N′)copper(II)], C38H30Cu3N8O20
  32. The crystal structure of (E)-1-ferrocenyl-3-(naphthalen-1-yl)prop-2-en-1-one, C23H18FeO
  33. The crystal structure of (E)-1-ferrocenyl-3-(4-isopropylphenyl)prop-2-en-1-one, C22H22FeO
  34. Crystal structure of 6-hydroxy-2,2-dimethyl-4Hbenzo[d][1,3]dioxin-4-one, C10H10O4
  35. The crystal structure of (2E,4E)-1-ferrocenyl-5-phenylpenta-2,4-dien-1-one, C21H18FeO
  36. Crystal structure of alaninato-κ2N,O-bis(hydroxylamido-κ2N,O)-oxido-vanadium(V), C3H10N3O5V
  37. Crystal structure of catena-poly[aqua-bis[μ2-6-(1H-imidazol-1-yl)nicotinato-κ2 N,O]copper(II)], C18H14N6O5Cu
  38. Crystal structure of diethyl 4,6-diphenyl-1,9-di-p-tolylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta[b]pyridine-3,5(2H)-dicarboxylate, C42H42N2O4
  39. The crystal structure of cobalt cadmium bis(hydrogenphosphate) bis(phosphate(V)) tetrahydrate, H10O20P4Co3.14Cd1.86
  40. Crystal structure of dimethyl 1,4,6,9-tetraphenylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta[b]pyridine-3,7(2H)-dicarboxylate, C38H34N2O4
  41. Crystal structure of (Z)-4-(furan-2-yl((4-iodophenyl)amino)methylene)-5-methyl-2(p-tolyl)-2,4-dihydro-3H-pyrazol-3-one, C21H16I N3O2
  42. Crystal structure of (E)-1-(4-(3,5-dimethoxystyryl)phenyl)-7-ethylheptanedioate, C25H30O6
  43. Crystal structure of 6-bromo-2-(4-chlorophenyl)chroman-4-one (6-bromo-4′-chloroflavanone), C15H10BrClO2
  44. The crystal structure of 2-(benzhydryloxy)-3-nitropyridine, C18H14N2O3
  45. The crystal structure of 1,3(4,1)-dipyridin-1-iuma-2(1,8)-diethynylanthracena-5(1,3)-benzenacyclohexaphane-11,31-diium bis(hexafluoridophosphate), C36H24F12N2P2
  46. Crystal structure of 3,6-di-tert-butyl-1-iodo-9-methyl-8-(pyren-1-ylethynyl)-9H-carbazole, C39H34IN
  47. The cocrystal 2-(dimethylammonio)-5-nitrobenzoate – 2-(dimethylamino)-5-nitrobenzoic acid, C9H10N2O4
  48. Crystal structure of 5-nitroquinazolin-4(3H)-one, C8H5N3O3
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