Home Crystal structure of 3,3′-(pyridine-2,6-diylbis(methylene))bis(1-propyl-1H-imidazol-3-ium) ditetrafluoroborate, C19H27B2F8N5
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Crystal structure of 3,3′-(pyridine-2,6-diylbis(methylene))bis(1-propyl-1H-imidazol-3-ium) ditetrafluoroborate, C19H27B2F8N5

  • David O. Ywaya , Holger B. Friedrich , Muhammad D. Bala ORCID logo EMAIL logo , Lynette Soobramoney and Halliru Ibrahim
Published/Copyright: March 16, 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

C19H27N5, orthorhombic Pbca (no. 61), a = 9.8515(12) Å, b = 16.508(2) Å, c = 29.817(3) Å, β = 90°, V = 4849.3(10) Å3, Z = 8, R gt (F) = 0.0409, wRref(F2) = 0.1082.

CCDC no.: 2152011

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colorless plate
Size: 0.27 × 0.22 × 0.14 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.13 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 28.3°, >99%
N(hkl)measured, N(hkl)unique, Rint: 31,833, 5336, 0.029
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 4368
N(param)refined: 337
Programs: Bruker [1], Olex2 [2], SHELX [3, 4], WinGX/ORTEP [5]
Table 2:

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

Atom x y z Uiso*/Ueq
B1 0.74157 (17) 0.90551 (10) 0.74844 (6) 0.0234 (3)
B2 0.14461 (17) 0.69821 (10) 0.55973 (5) 0.0217 (3)
C1 0.4246 (2) 0.60186 (11) 0.81026 (6) 0.0438 (5)
H1A 0.376509 0.570499 0.787324 0.066*
H1B 0.370936 0.602651 0.837924 0.066*
H1C 0.513040 0.576852 0.816193 0.066*
C2 0.44571 (19) 0.68936 (10) 0.79347 (5) 0.0325 (4)
H2A 0.356204 0.713743 0.786725 0.039*
H2B 0.488354 0.721732 0.817608 0.039*
C3 0.53546 (18) 0.69356 (11) 0.75121 (6) 0.0339 (4)
H3A 0.626555 0.671674 0.758273 0.041*
H3B 0.546437 0.750852 0.742108 0.041*
C4 0.36837 (15) 0.67242 (9) 0.68566 (5) 0.0245 (3)
H4 0.324407 0.723604 0.686676 0.029*
C5 0.33921 (15) 0.60988 (9) 0.65713 (5) 0.0242 (3)
H5 0.272049 0.609724 0.634269 0.029*
C6 0.50776 (14) 0.56966 (9) 0.70181 (5) 0.0221 (3)
H6 0.576152 0.537467 0.715481 0.026*
C7 0.43525 (17) 0.46741 (9) 0.64459 (5) 0.0274 (3)
H7A 0.342503 0.448128 0.637558 0.033*
H7B 0.478197 0.427248 0.664749 0.033*
C8 0.51809 (15) 0.47322 (9) 0.60082 (5) 0.0212 (3)
C9 0.53983 (16) 0.40225 (9) 0.57566 (5) 0.0248 (3)
H9 0.502033 0.352030 0.584934 0.030*
C10 0.61881 (16) 0.40739 (9) 0.53645 (5) 0.0273 (3)
H10 0.636432 0.360443 0.518974 0.033*
C11 0.67140 (16) 0.48328 (9) 0.52351 (5) 0.0255 (3)
H11 0.725178 0.488521 0.497227 0.031*
C12 0.64225 (15) 0.55131 (9) 0.55054 (5) 0.0210 (3)
C13 0.69277 (16) 0.63536 (9) 0.53542 (5) 0.0246 (3)
H13A 0.644771 0.650911 0.507543 0.029*
H13B 0.790854 0.631921 0.528453 0.029*
C14 0.55351 (15) 0.73926 (9) 0.57695 (5) 0.0215 (3)
H14 0.472407 0.733089 0.560052 0.026*
C15 0.76584 (15) 0.72439 (9) 0.60168 (5) 0.0239 (3)
H15 0.856555 0.705588 0.604567 0.029*
C16 0.70346 (15) 0.78112 (9) 0.62814 (5) 0.0241 (3)
H16 0.742930 0.809464 0.652609 0.029*
C17 0.47043 (16) 0.85037 (10) 0.62913 (5) 0.0274 (3)
H17A 0.477677 0.854389 0.662170 0.033*
H17B 0.377324 0.832184 0.621726 0.033*
C18 0.49573 (18) 0.93455 (10) 0.60811 (6) 0.0307 (4)
H18A 0.434786 0.974469 0.622543 0.037*
H18B 0.590411 0.951156 0.614378 0.037*
C19 0.4719 (2) 0.93634 (11) 0.55697 (6) 0.0403 (4)
H19A 0.537253 0.900436 0.542170 0.060*
H19B 0.483904 0.991756 0.545865 0.060*
H19C 0.379434 0.917971 0.550384 0.060*
F1 0.77417 (12) 0.84260 (6) 0.77795 (4) 0.0493 (3)
F2 0.77939 (10) 0.98057 (6) 0.76741 (3) 0.0358 (2)
F3 0.60173 (10) 0.90432 (7) 0.74013 (5) 0.0522 (3)
F4 0.81231 (12) 0.89578 (7) 0.70765 (3) 0.0501 (3)
F5 0.03182 (10) 0.71304 (6) 0.53157 (3) 0.0353 (2)
F6Aa 0.1795 (2) 0.61542 (8) 0.55926 (5) 0.0403 (4)
F6Bb 0.2349 (12) 0.6372 (7) 0.5512 (3) 0.0344 (19)
F7Aa 0.11646 (18) 0.72291 (12) 0.60368 (4) 0.0418 (4)
F7Bb 0.0872 (12) 0.6873 (9) 0.6023 (3) 0.045 (3)
F8Aa 0.25513 (13) 0.74281 (11) 0.54236 (6) 0.0448 (5)
F8Bb 0.2284 (10) 0.7690 (5) 0.5625 (4) 0.0337 (18)
N1 0.47551 (13) 0.64657 (8) 0.71311 (4) 0.0232 (3)
N2 0.42655 (12) 0.54648 (7) 0.66793 (4) 0.0207 (3)
N3 0.56774 (12) 0.54712 (7) 0.58879 (4) 0.0214 (3)
N4 0.67120 (12) 0.69936 (7) 0.56968 (4) 0.0201 (3)
N5 0.57062 (12) 0.78936 (7) 0.61226 (4) 0.0205 (3)

  1. aOccupancy: 0.882 (4), bOccupancy: 0.118 (4).

Source of material

The title compound was prepared using a method described in the literature [6]. In a 50 mL round-bottom flask, N-propyl imidazole (1.0 mmol) and 2,6-bis(chloromethyl)pyridine (0.5 mmol) were gently stirred together under inert conditions. The temperature was gradually raised, and the neat molten mixture maintained at 60 °C for 16 h. The light brown crude solid that resulted was allowed to cool to room temperature before being loaded onto a short plug of silica gel. The unreacted starting materials were washed with EtOAc, and the product salt bearing dichloride counterions was obtained as an eluent of MeOH (100%). Removal of all volatiles under reduced pressure gave the bisimidazolium dichloride salt as clear viscous oil in excellent yield. Successively, anionic metathesis of the chloride salt was achieved by dropwise addition of saturated aqueous solution of NaBF4 (2.5 mol equiv.) to its methanolic solution. The resultant mixture was then stirred at room temperature for 20 h. At the end of the reaction time, the contents in the reaction flask were concentrated under vacuum and organics extracted with acetone (3 × 20 mL). Subsequent solvent removal afforded the title compound as a brown solid: yield 0.25 g (90%). Colorless single crystals suitable for X-ray analysis were obtained by layering the methanolic solution of the title compound with diethyl ether [7, 8]. 1 H NMR (CD3CN, 400 MHz) δ/ppm: 0.90 (t, J = 7.4 Hz, 2 × 3H, CH3); 1.87 (m, 2 × 2H, CH2); 4.26 (t, J = 7.2 Hz, 2 × 2H, CH2); 5.54 (s, 2 × 2H, CH2(lutidyl)); 7.46 (d, J = 1.5 Hz, 2 × 1H, CHlutidyl) 7.53 (d, J = 7.7 Hz, 2 × 1H, –CH=imidazolyl), 7.60 (t, J = 1.6 Hz, 2 × 1H, =CH–imidazolyl), 7.87 (t, J = 7.7 Hz, 1H, CHlutidyl); 9.83 (s, 2 × 1H, NCHNimidazolyl). 13 C NMR (CD3CN, 100.6 MHz) δ/ppm: 10.84 (CH3), 24.22 (CH2), 51.92(CH2), 54.19 (CH2(lutidyl)), 122.92, 123; 89, 124.10, 139.91, 154.57 (NCHN). HRMS-ES + : (m/z)/2: calcd for [(M – 2BF4)]/2 162.6128, found 162.6140.

Experimental details

Crystal evaluation was carried out using a Bruker APEX-II diffractometer [1] outfitted with an Oxford Cryostream low-temperature apparatus set to 104 K. The structure was solved with the ShelXT [3] structure solution program using Intrinsic Phasing and refined with the ShelXL [4] refinement package. Uiso was fixed at 1.2 times of C(H) and C(H, H) groups and at 1.5 times of C(H, H, H) group and secondary CH2 and aromatic H were refined with riding coordinates. Methyl was idealized and refined as a rotating group. The visual crystal structure information was performed using ORTEP-3 [5].

Comment

When adequately constituted, the title compound can be a convenient source of ionic liquid (IL) solvents [7, 8]; it is also a credible alternative to phosphines in organometallic chemistry and catalysis [9]. More importantly, when combined with metal ions, the complexes have been used as catalysts in various applications [10–12].

The title structure is composed of one cationic pyridine bridged bis-imidazole core and two tetrafluoroborate anions occupying the asymmetric unit. Both imidazole units in the title structure are almost perpendicular to the plane of the central pyridine unit, and the imidazole C-2 protons are directed well away from each other. The internal ring angle of imidazole (N–C–N) is 108.35(13) for N1–C6–N2 and 108.47(12) for N4–C14–N5, which are well within the range for related imidazole-based salts [13, 14]. A series of weak C–H···F hydrogen bonding interactions between the counterions and the core salt, which were observed in the extended structure of the compound, stabilized the crystal packing.

Corresponding author: Muhammad D. Bala, School of Chemistry, University of Kwazulu-Natal, Private Bag X54001, Durban 4001, South Africa, E-mail:

Funding source: NRF

Funding source: SASOL

Acknowledgment

Mr. Sizwe J. Zamisa is acknowledged for crystal data collection and refinement.

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

  2. Research funding: This study received post-doctoral fellowships from NRF (LS) and SASOL (HI).

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

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Received: 2022-02-17
Accepted: 2022-03-03
Published Online: 2022-03-16
Published in Print: 2022-06-27

© 2022 David O. Ywaya 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-2022-0078
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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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