Startseite The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 2-carboxy-6-nitrobenzoate monohydrate, C24H25FN4O10
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The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 2-carboxy-6-nitrobenzoate monohydrate, C24H25FN4O10

  • Yu-Yun Sun , Zhan-Ning Gu und Cheng-Jun Jiang ORCID logo EMAIL logo
Veröffentlicht/Copyright: 1. Juli 2024

Abstract

C24H25FN4O10, triclinic, P1̄ (no. 2), a = 7.7217(3) Å, b = 9.9451(4) Å, c = 15.9291(6) Å, α = 101.741(1), β = 98.762(1), γ = 96.148(1), V = 1171.56(8) Å3, Z = 2, R gt (F) = 0.0389, wR ref (F2) = 0.1162, T = 170 K.

CCDC no.: 2359349

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: Colourless needle
Size: 0.08 × 0.05 × 0.03 mm
Wavelength:

μ:
Ga Kα radiation (1.34139 Å)

0.70 mm−1
Diffractometer, scan mode:

θmax, completeness:
Bruker D8 Venture, φ and ω

60.6°, 99 %
N(hkl)measured, N(hkl)unique, Rint: 22065, 5,307, 0.029
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 4,883
N(param)refined: 358
Programs: Bruker, 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 0.82066 (11) −0.38467 (8) 0.42201 (5) 0.03345 (19)
O1 0.66996 (12) 0.03211 (10) 0.61742 (5) 0.0286 (2)
N1 0.90979 (13) −0.47973 (10) 0.10751 (6) 0.0233 (2)
H1A 0.833283 −0.447732 0.069417 0.028*
H1B 0.956655 −0.549644 0.076413 0.028*
C1 0.97903 (15) −0.25270 (12) 0.20977 (7) 0.0221 (2)
H1C 1.074780 −0.176157 0.240036 0.026*
H1D 0.890636 −0.214860 0.172627 0.026*
O2 0.63521 (15) 0.43385 (10) 0.59836 (6) 0.0379 (2)
N2 0.89504 (13) −0.30954 (10) 0.27403 (6) 0.0214 (2)
C2 1.05459 (15) −0.36535 (13) 0.15380 (8) 0.0248 (2)
H2A 1.112463 −0.326690 0.110803 0.030*
H2B 1.144868 −0.401830 0.190751 0.030*
O3 0.60524 (12) 0.27272 (10) 0.67515 (6) 0.0308 (2)
H3 0.617780 0.188716 0.669894 0.046*
N3 0.78302 (12) 0.15793 (10) 0.39932 (6) 0.0205 (2)
C3 0.8119 (2) −0.53438 (13) 0.16972 (9) 0.0315 (3)
H3A 0.890624 −0.581773 0.205398 0.038*
H3B 0.709714 −0.603457 0.136821 0.038*
C4 0.74645 (17) −0.41914 (12) 0.22898 (8) 0.0267 (3)
H4A 0.656522 −0.379030 0.194217 0.032*
H4B 0.689960 −0.457231 0.272583 0.032*
C5 0.84821 (14) −0.21132 (12) 0.34031 (7) 0.0201 (2)
C6 0.80972 (15) −0.25177 (12) 0.41629 (8) 0.0227 (2)
C7 0.76379 (15) −0.16312 (12) 0.48356 (7) 0.0222 (2)
H7 0.736719 −0.194977 0.533025 0.027*
C8 0.75667 (14) −0.02376 (12) 0.47929 (7) 0.0201 (2)
C9 0.79536 (14) 0.02060 (11) 0.40507 (7) 0.0191 (2)
C10 0.84165 (14) −0.07380 (12) 0.33625 (7) 0.0201 (2)
H10 0.868724 −0.042994 0.286453 0.024*
C11 0.73608 (15) 0.24582 (12) 0.46474 (8) 0.0231 (2)
H11 0.727702 0.338285 0.459103 0.028*
C12 0.69938 (15) 0.20951 (12) 0.53955 (7) 0.0231 (2)
C13 0.70641 (14) 0.07129 (12) 0.55066 (7) 0.0217 (2)
C14 0.81829 (15) 0.20750 (12) 0.32101 (7) 0.0230 (2)
H14A 0.763193 0.292469 0.318963 0.028*
H14B 0.761989 0.135917 0.268298 0.028*
C15 1.01419 (17) 0.23901 (14) 0.31947 (9) 0.0308 (3)
H15A 1.029727 0.259563 0.263239 0.046*
H15B 1.072050 0.158452 0.327711 0.046*
H15C 1.067374 0.319388 0.366458 0.046*
C16 0.64498 (16) 0.31519 (13) 0.60687 (8) 0.0269 (3)
O10 0.38416 (14) 0.60966 (11) 1.05019 (9) 0.0433 (3)
H10A 0.485331 0.631242 1.035084 0.065*
H10B 0.391500 0.530358 1.064586 0.065*
O4 0.66143 (15) 0.57861 (9) 0.81606 (6) 0.0395 (3)
N4 0.79564 (13) 1.02865 (10) 1.06666 (6) 0.0215 (2)
O5 0.58881 (12) 0.66569 (9) 0.69946 (6) 0.0283 (2)
H5 0.592184 0.584237 0.672742 0.042*
O6 0.95731 (11) 0.71750 (8) 0.95711 (6) 0.02618 (19)
O7 0.71414 (12) 0.68610 (9) 1.01464 (6) 0.0285 (2)
O8 0.91238 (13) 0.97068 (9) 1.09879 (6) 0.0309 (2)
O9 0.72957 (12) 1.12160 (9) 1.10849 (6) 0.0309 (2)
C17 0.64101 (14) 0.67752 (12) 0.78442 (8) 0.0219 (2)
C18 0.66377 (14) 0.82306 (11) 0.83658 (7) 0.0192 (2)
C19 0.73179 (13) 0.85203 (11) 0.92663 (7) 0.0177 (2)
C20 0.73068 (14) 0.98709 (11) 0.97208 (7) 0.0190 (2)
C21 0.67283 (15) 1.09082 (11) 0.93336 (8) 0.0229 (2)
H21 0.672012 1.180840 0.967595 0.028*
C22 0.61614 (16) 1.06125 (12) 0.84390 (8) 0.0244 (2)
H22 0.580805 1.131951 0.815732 0.029*
C23 0.61150 (15) 0.92771 (12) 0.79598 (7) 0.0220 (2)
H23 0.572243 0.907027 0.734672 0.026*
C24 0.80767 (15) 0.74162 (11) 0.96971 (7) 0.0201 (2)

1 Source of materials

The mixture of norfloxacin (16.0 mg, 0.05 mmol) and 3-nitrophthalic acid (10.6 mg, 0.05 mmol) was dissolved in a mixture of 2 ml deionized water and 2 ml ethanol. The resulting mixture was stirred and dissolved in a temperature water bath at 60°C during 30 min; then filtered and placed in a 10 ml glass bottle. The filtrate was slowly evaporated at room temperature. Crystals of the title compound were obtained after 2 days.

2 Experimental details

Absorption corrections were applied by using multi-scan program. 1 Using Olex2, 2 the structure was solved with the ShelXT 3 structure solution program and refined with the ShelXL 4 refinement package. The H atoms were fixed, fixed Uiso were set to 1.2 times of all C(H) groups, C(H,H) groups and N(H,H) groups; 1.5 times of C(H,H,H,H) groups, O(H) groups and O(H,H) groups.

3 Comment

Norfloxacin is a potent fluoroquinolone antibacterial compound, which is widely used in the treatment of various bacterial infections caused by both Gram-positive and Gram-negative bacteria. 5 The aqueous solubility of fluoroquinolones is improved by salts or cocrystals. A series of crystalline salts or cocrystals of norfloxacin have been obtained and characterised. 6 10 The aim of this study is to investigate the structural properties of a new norfloxacin salt. The title crystal was formed by protonated Norfloxacin and the deprotonated 3-nitrophthalic acid molecules through intermolecular hydrogen bonds, H5O5⋯O2(d(O5⋯O2) = 2.623 Å). Water and 3-nitrophthalate anions are connected through intermolecular hydrogen bonds H10AO10…O7(d(O5⋯O2) = 2.775 Å). Meanwhile, the protonated Norfloxacin has an intramolecular hydrogen bond H3O3⋯O1(d(O3⋯O1) = 2.541 Å). The 3-nitrophthalate anion shows two intramolecular hydrogen bonds O7⋯O8(d(O7⋯O8) = 3.009 Å) and O4⋯O6(d(O4⋯O6) = 2.945 Å). H1AN1 and H1BN1 in the piperazine group participate in a classical bond to the oxygen atom in the 3-nitrophthalate anion N1⋯O6(d(N1⋯O6) = 2.749 Å), N1⋯O7(d(N1⋯O7) = 2.835 Å).


Corresponding author: Cheng-Jun Jiang, School of Biological and Chemical Engineering, Zhejiang University of Science and Technology, Hangzhou Liuhe Road 318#, China, E-mail:

Acknowledgements

We would also like to thank Mr Jiyong Liu from the Chemistry Instrumentation Center Zhejiang University for X-ray crystallographic analysis.

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

  2. Competing interests: The authors declare no conflicts of interest regarding this article.

References

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Received: 2024-05-08
Accepted: 2024-05-30
Published Online: 2024-07-01
Published in Print: 2024-10-28

© 2024 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. Editorial
  3. Editorial 2024 – New developments and changes of Zeitschrift für Kristallographie – New Crystal Structures
  4. New Crystal Structures
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  19. Crystal structure of poly[bis(4-(4-(pyridin-4-yl)phenyl)pyridin-1-ium-κ1N)-(μ4-benzene-1,2,4,5-tetracarboxylato-κ5O:O′: O″:O‴:O⁗)-(μ2-2,5-dicarboxyterephthalato-κ2O:O′)dizinc(II)], C52H32N4O16Zn2
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  27. Crystal and molecular structure of 5-bromopyridine-2,3-diamine
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  29. Crystal structure of thiocyanate-κ1N-bis(μ1-2,6-diformyl-4-methylphenol oxime-κ2N,O)-manganese(III) acetonitrile solvate, C21H21MnN6O6S
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  53. The crystal structure of 6-amino-pyridinium-2-carboxylate, C6H6N2O2
  54. The crystal structure of catena-poly[aqua-nitrato-κ3O,O:O′′-(1,10-phenanthroline-κ2N,N)sodium(I)], C24H18N6O7Na2
  55. Retractions
  56. Retraction of: Crystal structure of bis[diaquaisonicotinatosamarium(III)]-µ-isonicotinato-[diisonicotinatocopper(II)], CuSm2(C6H4NO2)8(H2O)4
  57. Retraction of: Crystal structure of aqua(2,2-bipyridine-k 2 N:N′)(nitrato)-(4-aminobenzoato)cadmium(II) nitrate, [Cd(H2O)(NO3)(C10H8N2)(C7H7NO2)][NO3]
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