Norfloxacinium nitrate

Rasulov, A.; Torambetov, B.; Alimnazarov, B.; Kadirova, S.; Suyunov, J.; Nazarov, Y.; Ashurov, J.

doi:10.1107/S2414314624008137

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 9| Part 8| August 2024| x240813

https://doi.org/10.1107/S2414314624008137

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Norfloxacinium nitrate

Abdusamat Rasulov,^a Batirbay Torambetov,^b ^* Bekmurod Alimnazarov,^c Shakhnoza Kadirova,^b Jabbor Suyunov,^c Yusufjon Nazarov ^c and Jamshid Ashurov ^a

^aInstitute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, M. Ulugbek St 83, Tashkent, 100125, Uzbekistan, ^bNational University of Uzbekistan named after Mirzo Ulugbek, 4 University St, Tashkent, 100174, Uzbekistan, and ^cTermez State University, Barkamol Avlod St 43, Termez, 190111, Uzbekistan
^*Correspondence e-mail: torambetov_b@mail.ru

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 30 July 2024; accepted 16 August 2024; online 30 August 2024)

In the title salt [systematic name: 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium nitrate], C₁₆H₁₉FN₃O₃⁺·NO₃⁻, proton transfer from nitric acid to the N atom of the piperazine ring of norfloxacin has occurred to form a molecular salt. In the extended structure, N—H⋯O hydrogen bonds link alternating cations and anions into [100] chains, which are reinforced by aromatic π–π stacking interactions between the quinoline moieties of the norfloxacinium cations.

Keywords: crystal structure; norfloxacin; molecular structure; hydrogen bonds.

CCDC reference: 2378009

Structure description

Norfloxacin (NF, C₁₆H₁₈N₃O₃F) is a synthetic fluoroquinolone antibiotic that has been used to treat a wide variety of bacterial infections since its introduction in the 1980s. It is effective against both Gram-positive and Gram-negative bacteria, and it has been shown to be particularly useful in the treatment of urinary tract infections, respiratory tract infections, and skin and soft tissue infections. Norfloxacin works by inhibiting the bacterial enzyme DNA gyrase, which is essential for DNA replication and transcription (Goldstein et al., 1987 ; Mazuel, 1991 ; Chongcharoen et al., 2008 ; Marc et al., 2019 ; Spencer et al., 2023 ). As part of our studies in this area we now describe the synthesis and structure of the title molecular salt, C₁₆H₁₉N₃O₃F⁺·NO₃⁻, (I), arising from the reaction of norfloxacin and nitric acid in aqueous solution.

Compound (I) crystallizes in the monoclinic space group P2₁/n, with one cation and one anion in the asymmetric unit (Fig. 1). The N3 nitrogen atom of the piperazine ring is observed to be protonated. In neutral NF, this nitrogen atom is protonated by a hydrogen atom from the carboxylic acid moiety, resulting in a zwitterionic species (e.g., Gunnam & Nangia, 2023 ). However, in the crystal structure of (I), the hydrogen atom remains attached to the carboxylic acid fragment. This is evident from the significant difference (0.117 Å) in the lengths of the C10—O1 and C10—O2 bonds [1.325 (2) and 1.208 (2) Å, respectively]. In a delocalized carboxylic acid moiety, the C—O bond lengths are typically very similar, with a difference of only 0.006 Å (Razzoqova et al., 2022 ). The atoms of the carboxyl moiety (C10, O1, and O2) and the quinoline moiety lie essentially in a plane, with maximum deviations from the mean plane of 0.029 (2) Å for O2 and 0.030 (2) Å for O1. The dihedral angle between the carboxyl and quinoline planes is 1.90 (19)°. The nitrogen atom (N2) attached to the quinoline moiety is close to planar, as evidenced by the sum of bond angles around it being 356.5°. In contrast, the protonated nitrogen atom (N3) adopts a tetrahedral geometry. The piperazine ring exhibits a chair conformation. The ethyl substituent attached to N1 lies essentially in the plane of the quinoline moiety, as indicated by the C1—N1—C11—C12 torsion angle of 0.7 (2)°. The C5—F1 bond length of 1.3506 (18) Å is in good agreement with the mean value reported for 128 structures containing the NF moiety [e.g., 1.350 (2) Å reported by Sultana et al., 2023 ]. Atom F1 accepts an intramolecular hydrogen bond from H13B (C13—H13B⋯F1; Table 1), forming an S(6) ring. Another intramolecular hydrogen bond is observed between H1 and O3 (O1—H1⋯O3), also forming a six-membered ring. Additionally, a weak hydrogen bond is present between H1A and O2 (C1—H1A⋯O2), forming a five-membered ring.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3	0.82	1.80	2.5640 (17)	154
N3—H3B⋯O4	0.89	1.97	2.8526 (19)	169
N3—H3A⋯O6ⁱ	0.89	2.08	2.937 (2)	161
C13—H13B⋯F1	0.97	1.96	2.726 (2)	135
C15—H15A⋯O4ⁱⁱ	0.97	2.47	3.252 (2)	138
Symmetry codes: (i) ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Figure 1
The molecular structure of (I). Displacement ellipsoids are shown at the 50% probability level and hydrogen bonds are indicated by dashed lines.

In the extended structure of (I), the norflaxacinium cation forms a hydrogen bond with the nitrate anion via its NH group (N3—H3B⋯O4). The nitrate anion, in turn, accepts a hydrogen bond from the NH group (N3—H3A⋯O6) of an adjacent NF cation related by the symmetry operation 1 + x, y, z (Table 1). These hydrogen bonds generate an infinite chain of alternating cations and anions propagating along the [100] direction (Fig. 2). This packing arrangement is repeated on the opposite side of the chain. As a result, strong π–π stacking interactions are formed between layers of NF cations facing each other (Fig. 3). The π–π stacking interactions are observed between the original NF cation and its symmetry-related counterparts located at −x, 1 − y, 1 − z and 1 − x, 1 − y, 1 − z. These interactions are highlighted by the short centroid–centroid distances: Cg1–Cg3(−x, 1 − y, 1 - z) is 3.6182 (8) Å and Cg1–Cg1 is 3.4403 (7) Å, and Cg1–Cg3(1 − x, 1 − y, 1 − z) is 3.5919 (8) Å and Cg1–Cg1 is 3.4862 (7) Å. These distances are notably shorter than the centroid–centroid contacts reported by Ibukun et al. (2023 ) and Shaikh et al. (2024 ). The angle between the mean planes of the quinoline moieties is zero by symmetry. These stacking interactions also contribute to the packing of molecules along the [100] direction.

Figure 2
A fragment of a [100] chain in the extended structure of (I), with hydrogen bonds shown as dashed lines.

Figure 3
A view of the π–π stacking interaction along the a-axis direction.

Synthesis and crystallization

31.9 mg (0.1 mmol) of NF was dissolved in 5 ml of a 0.02 M nitric acid solution. The resulting clear solution was stirred at room temperature for 30 minutes. The solution was then transferred to a vial with small holes in the lid to allow for evaporation. After about a week, needle-like single crystals of the title salt suitable for data collection were obtained.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₁₉FN₃O₃⁺·NO₃⁻
M_r	382.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	6.6241 (1), 19.1629 (3), 12.6062 (2)
β (°)	93.136 (1)
V (Å³)	1597.80 (4)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	1.12
Crystal size (mm)	0.12 × 0.06 × 0.06

Data collection
Diffractometer	XtaLAB Synergy, Single source at home/near, HyPix3000
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2020 $[Rigaku OD (2020). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, England.]$ )
T_min, T_max	0.977, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	15217, 3087, 2593
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.126, 1.05
No. of reflections	3087
No. of parameters	248
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.40
Computer programs: CrysAlis PRO (Rigaku OD, 2020 $[Rigaku OD (2020). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, England.]$ ), SHELXT2019/3 (Sheldrick, 2015a ), SHELXL2018/2 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 2378009

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314624008137/hb4480sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314624008137/hb4480Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314624008137/hb4480Isup3.cml

checkCIF report

Computing details top

4-(3-Carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium nitrate top

Crystal data top

C₁₆H₁₉FN₃O₃⁺·NO₃⁻	F(000) = 800
M_r = 382.35	D_x = 1.589 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
a = 6.6241 (1) Å	Cell parameters from 6698 reflections
b = 19.1629 (3) Å	θ = 4.2–71.2°
c = 12.6062 (2) Å	µ = 1.12 mm⁻¹
β = 93.136 (1)°	T = 293 K
V = 1597.80 (4) Å³	Block, colourless
Z = 4	0.12 × 0.06 × 0.06 mm

Data collection top

XtaLAB Synergy, Single source at home/near, HyPix3000 diffractometer	3087 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	2593 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.030
Detector resolution: 10.0000 pixels mm^-1	θ_max = 71.4°, θ_min = 4.2°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2020)	k = −23→22
T_min = 0.977, T_max = 1.000	l = −15→15
15217 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0705P)² + 0.357P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3087 reflections	Δρ_max = 0.30 e Å⁻³
248 parameters	Δρ_min = −0.40 e Å⁻³
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
F1	0.2303 (3)	0.44122 (6)	0.15882 (8)	0.0807 (5)
O1	0.2724 (2)	0.35903 (6)	0.73719 (10)	0.0472 (4)
H1	0.263362	0.345934	0.675190	0.071*
O2	0.2684 (2)	0.45919 (7)	0.82376 (9)	0.0495 (4)
O3	0.25105 (18)	0.35942 (6)	0.53350 (9)	0.0402 (3)
N1	0.25398 (17)	0.57393 (6)	0.54595 (9)	0.0268 (3)
N2	0.2332 (2)	0.59041 (7)	0.16174 (9)	0.0329 (3)
N3	0.3057 (2)	0.67660 (7)	−0.01891 (11)	0.0377 (4)
H3A	0.182223	0.688245	−0.044283	0.045*
H3B	0.394911	0.696219	−0.059962	0.045*
C1	0.2601 (2)	0.53477 (8)	0.63385 (11)	0.0291 (4)
H1A	0.265330	0.557750	0.698925	0.035*
C2	0.2592 (2)	0.46329 (8)	0.63512 (11)	0.0294 (4)
C3	0.2514 (2)	0.42535 (8)	0.53739 (12)	0.0292 (4)
C4	0.2374 (2)	0.43679 (8)	0.34112 (12)	0.0321 (4)
H4	0.235928	0.388404	0.335394	0.039*
C5	0.2327 (3)	0.47623 (8)	0.25186 (12)	0.0354 (4)
C6	0.2319 (2)	0.55061 (8)	0.25178 (11)	0.0270 (4)
C7	0.2372 (2)	0.58073 (7)	0.35309 (11)	0.0274 (4)
H7	0.235217	0.629125	0.358517	0.033*
C8	0.24524 (19)	0.54122 (7)	0.44637 (11)	0.0256 (3)
C9	0.2443 (2)	0.46788 (8)	0.44236 (11)	0.0273 (4)
C10	0.2671 (2)	0.42813 (9)	0.74030 (12)	0.0351 (4)
C11	0.2604 (2)	0.65153 (8)	0.55207 (12)	0.0326 (4)
H11A	0.139091	0.669951	0.515682	0.039*
H11B	0.375099	0.667878	0.514330	0.039*
C12	0.2764 (3)	0.68081 (9)	0.66298 (13)	0.0422 (4)
H12A	0.280299	0.730842	0.659726	0.063*
H12B	0.397817	0.663933	0.699410	0.063*
H12C	0.161388	0.666340	0.700562	0.063*
C13	0.1897 (3)	0.56517 (9)	0.05373 (13)	0.0469 (5)
H13A	0.050313	0.575445	0.031684	0.056*
H13B	0.208003	0.514977	0.051602	0.056*
C14	0.3288 (4)	0.59967 (10)	−0.02121 (14)	0.0534 (5)
H14A	0.467697	0.587416	−0.001074	0.064*
H14B	0.298153	0.582794	−0.092826	0.064*
C15	0.2046 (3)	0.66574 (9)	0.16535 (13)	0.0490 (5)
H15A	0.234172	0.682163	0.237302	0.059*
H15B	0.064439	0.676689	0.145859	0.059*
C16	0.3382 (3)	0.70272 (9)	0.09163 (13)	0.0454 (5)
H16A	0.310319	0.752384	0.093207	0.055*
H16B	0.478515	0.695757	0.115461	0.055*
O4	0.62110 (18)	0.72318 (8)	−0.14696 (11)	0.0544 (4)
O5	0.7972 (2)	0.68395 (8)	−0.01286 (11)	0.0628 (5)
O6	0.9454 (2)	0.71910 (9)	−0.14916 (14)	0.0697 (5)
N4	0.7890 (2)	0.70827 (7)	−0.10335 (11)	0.0383 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.1802 (16)	0.0320 (6)	0.0297 (6)	0.0089 (7)	0.0057 (7)	−0.0077 (4)
O1	0.0642 (8)	0.0373 (7)	0.0399 (7)	0.0008 (6)	0.0013 (6)	0.0116 (5)
O2	0.0670 (9)	0.0511 (8)	0.0305 (7)	0.0034 (6)	0.0035 (5)	0.0060 (5)
O3	0.0526 (7)	0.0269 (6)	0.0409 (7)	−0.0004 (5)	0.0006 (5)	0.0042 (4)
N1	0.0280 (6)	0.0271 (7)	0.0252 (6)	0.0004 (4)	0.0003 (5)	−0.0005 (4)
N2	0.0462 (8)	0.0281 (7)	0.0244 (6)	−0.0018 (5)	0.0027 (5)	−0.0008 (5)
N3	0.0396 (7)	0.0417 (8)	0.0321 (7)	−0.0027 (6)	0.0042 (5)	0.0076 (5)
C1	0.0272 (7)	0.0348 (8)	0.0254 (7)	0.0004 (6)	0.0012 (5)	0.0012 (6)
C2	0.0246 (7)	0.0338 (8)	0.0296 (8)	0.0007 (5)	0.0011 (6)	0.0049 (6)
C3	0.0233 (7)	0.0284 (8)	0.0358 (8)	0.0004 (5)	0.0016 (6)	0.0039 (6)
C4	0.0370 (8)	0.0241 (7)	0.0352 (8)	0.0010 (6)	0.0020 (6)	−0.0005 (6)
C5	0.0495 (9)	0.0287 (8)	0.0281 (8)	0.0020 (7)	0.0036 (6)	−0.0061 (6)
C6	0.0251 (7)	0.0287 (8)	0.0272 (7)	−0.0010 (5)	0.0020 (5)	0.0011 (5)
C7	0.0296 (7)	0.0233 (7)	0.0291 (8)	−0.0009 (5)	0.0005 (5)	−0.0013 (5)
C8	0.0206 (6)	0.0287 (8)	0.0273 (8)	−0.0003 (5)	0.0010 (5)	−0.0004 (5)
C9	0.0232 (7)	0.0277 (8)	0.0311 (8)	0.0000 (5)	0.0011 (5)	0.0009 (5)
C10	0.0313 (8)	0.0395 (9)	0.0344 (9)	0.0010 (6)	0.0004 (6)	0.0091 (6)
C11	0.0389 (8)	0.0267 (8)	0.0320 (8)	0.0008 (6)	0.0004 (6)	−0.0012 (6)
C12	0.0558 (11)	0.0347 (9)	0.0357 (9)	0.0029 (7)	−0.0020 (7)	−0.0055 (6)
C13	0.0763 (13)	0.0368 (9)	0.0268 (8)	−0.0158 (8)	−0.0044 (8)	−0.0006 (6)
C14	0.0844 (15)	0.0448 (10)	0.0325 (9)	0.0064 (9)	0.0162 (9)	0.0002 (7)
C15	0.0866 (14)	0.0318 (9)	0.0296 (8)	0.0117 (8)	0.0129 (8)	0.0031 (6)
C16	0.0659 (12)	0.0318 (9)	0.0373 (9)	−0.0092 (8)	−0.0087 (8)	0.0048 (7)
O4	0.0380 (7)	0.0706 (9)	0.0537 (8)	−0.0043 (6)	−0.0058 (5)	0.0246 (6)
O5	0.0728 (10)	0.0773 (10)	0.0375 (7)	0.0144 (8)	−0.0061 (6)	0.0081 (6)
O6	0.0420 (8)	0.0876 (12)	0.0807 (11)	−0.0025 (7)	0.0152 (7)	0.0163 (9)
N4	0.0388 (8)	0.0353 (7)	0.0405 (8)	−0.0010 (6)	−0.0004 (6)	−0.0001 (6)

Geometric parameters (Å, º) top

C5—F1	1.3506 (18)	C6—C7	1.4002 (19)
O1—H1	0.8200	C7—H7	0.9300
C10—O1	1.325 (2)	C7—C8	1.3972 (19)
C10—O2	1.208 (2)	C8—C9	1.406 (2)
O3—C3	1.2643 (19)	C11—H11A	0.9700
N1—C1	1.3371 (18)	C11—H11B	0.9700
N1—C8	1.4015 (18)	C11—C12	1.505 (2)
N1—C11	1.4895 (18)	C12—H12A	0.9600
N2—C6	1.3679 (18)	C12—H12B	0.9600
N2—C13	1.4587 (19)	C12—H12C	0.9600
N2—C15	1.457 (2)	C13—H13A	0.9700
N3—H3A	0.8900	C13—H13B	0.9700
N3—H3B	0.8900	C13—C14	1.508 (3)
N3—C14	1.482 (2)	C14—H14A	0.9700
N3—C16	1.485 (2)	C14—H14B	0.9700
C1—H1A	0.9300	C15—H15A	0.9700
C1—C2	1.370 (2)	C15—H15B	0.9700
C2—C3	1.429 (2)	C15—C16	1.497 (3)
C2—C10	1.486 (2)	C16—H16A	0.9700
C3—C9	1.448 (2)	C16—H16B	0.9700
C4—H4	0.9300	O4—N4	1.2465 (18)
C4—C5	1.354 (2)	O5—N4	1.2307 (19)
C4—C9	1.407 (2)	O6—N4	1.2311 (19)
C5—C6	1.425 (2)

C10—O1—H1	109.5	O2—C10—O1	121.25 (14)
C1—N1—C8	119.29 (12)	O2—C10—C2	123.50 (15)
C1—N1—C11	121.19 (12)	N1—C11—H11A	108.5
C8—N1—C11	119.51 (11)	N1—C11—H11B	108.5
C6—N2—C13	125.43 (13)	N1—C11—C12	114.88 (12)
C6—N2—C15	121.32 (12)	H11A—C11—H11B	107.5
C15—N2—C13	109.78 (13)	C12—C11—H11A	108.5
H3A—N3—H3B	108.2	C12—C11—H11B	108.5
C14—N3—H3A	109.6	C11—C12—H12A	109.5
C14—N3—H3B	109.6	C11—C12—H12B	109.5
C14—N3—C16	110.09 (13)	C11—C12—H12C	109.5
C16—N3—H3A	109.6	H12A—C12—H12B	109.5
C16—N3—H3B	109.6	H12A—C12—H12C	109.5
N1—C1—H1A	117.6	H12B—C12—H12C	109.5
N1—C1—C2	124.81 (13)	N2—C13—H13A	109.6
C2—C1—H1A	117.6	N2—C13—H13B	109.6
C1—C2—C3	119.91 (13)	N2—C13—C14	110.09 (14)
C1—C2—C10	117.64 (13)	H13A—C13—H13B	108.2
C3—C2—C10	122.45 (14)	C14—C13—H13A	109.6
O3—C3—C2	122.81 (13)	C14—C13—H13B	109.6
O3—C3—C9	122.04 (14)	N3—C14—C13	110.89 (15)
C2—C3—C9	115.15 (13)	N3—C14—H14A	109.5
C5—C4—H4	119.5	N3—C14—H14B	109.5
C5—C4—C9	121.03 (14)	C13—C14—H14A	109.5
C9—C4—H4	119.5	C13—C14—H14B	109.5
F1—C5—C4	116.29 (14)	H14A—C14—H14B	108.0
F1—C5—C6	119.75 (13)	N2—C15—H15A	109.3
C4—C5—C6	123.96 (13)	N2—C15—H15B	109.3
N2—C6—C5	123.92 (13)	N2—C15—C16	111.55 (15)
N2—C6—C7	121.73 (13)	H15A—C15—H15B	108.0
C7—C6—C5	114.31 (12)	C16—C15—H15A	109.3
C6—C7—H7	118.6	C16—C15—H15B	109.3
C8—C7—C6	122.83 (13)	N3—C16—C15	111.25 (14)
C8—C7—H7	118.6	N3—C16—H16A	109.4
N1—C8—C9	118.62 (12)	N3—C16—H16B	109.4
C7—C8—N1	120.62 (13)	C15—C16—H16A	109.4
C7—C8—C9	120.76 (13)	C15—C16—H16B	109.4
C4—C9—C3	120.68 (14)	H16A—C16—H16B	108.0
C8—C9—C3	122.21 (13)	O5—N4—O4	119.25 (15)
C8—C9—C4	117.11 (13)	O5—N4—O6	120.21 (15)
O1—C10—C2	115.24 (14)	O6—N4—O4	120.52 (15)

F1—C5—C6—N2	−1.5 (2)	C5—C4—C9—C8	0.3 (2)
F1—C5—C6—C7	−179.23 (15)	C5—C6—C7—C8	0.8 (2)
O3—C3—C9—C4	−0.3 (2)	C6—N2—C13—C14	−141.27 (16)
O3—C3—C9—C8	−179.83 (13)	C6—N2—C15—C16	141.16 (15)
N1—C1—C2—C3	0.1 (2)	C6—C7—C8—N1	178.83 (12)
N1—C1—C2—C10	179.87 (13)	C6—C7—C8—C9	−1.3 (2)
N1—C8—C9—C3	0.18 (19)	C7—C8—C9—C3	−179.68 (13)
N1—C8—C9—C4	−179.42 (12)	C7—C8—C9—C4	0.7 (2)
N2—C6—C7—C8	−177.03 (13)	C8—N1—C1—C2	0.2 (2)
N2—C13—C14—N3	−58.8 (2)	C8—N1—C11—C12	−178.10 (13)
N2—C15—C16—N3	56.1 (2)	C9—C4—C5—F1	178.70 (15)
C1—N1—C8—C7	179.51 (12)	C9—C4—C5—C6	−0.8 (2)
C1—N1—C8—C9	−0.34 (18)	C10—C2—C3—O3	−0.1 (2)
C1—N1—C11—C12	0.7 (2)	C10—C2—C3—C9	179.98 (13)
C1—C2—C3—O3	179.71 (14)	C11—N1—C1—C2	−178.54 (13)
C1—C2—C3—C9	−0.23 (19)	C11—N1—C8—C7	−1.70 (19)
C1—C2—C10—O1	−177.93 (13)	C11—N1—C8—C9	178.45 (12)
C1—C2—C10—O2	2.2 (2)	C13—N2—C6—C5	14.7 (2)
C2—C3—C9—C4	179.68 (13)	C13—N2—C6—C7	−167.66 (16)
C2—C3—C9—C8	0.10 (19)	C13—N2—C15—C16	−58.8 (2)
C3—C2—C10—O1	1.9 (2)	C14—N3—C16—C15	−53.7 (2)
C3—C2—C10—O2	−178.01 (15)	C15—N2—C6—C5	171.54 (16)
C4—C5—C6—N2	178.02 (15)	C15—N2—C6—C7	−10.8 (2)
C4—C5—C6—C7	0.2 (2)	C15—N2—C13—C14	59.7 (2)
C5—C4—C9—C3	−179.32 (14)	C16—N3—C14—C13	55.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.82	1.80	2.5640 (17)	154
N3—H3B···O4	0.89	1.97	2.8526 (19)	169
N3—H3A···O6ⁱ	0.89	2.08	2.937 (2)	161
C13—H13B···F1	0.97	1.96	2.726 (2)	135
C15—H15A···O4ⁱⁱ	0.97	2.47	3.252 (2)	138

Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+3/2, z+1/2.

References

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Volume 9| Part 8| August 2024| x240813

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Norfloxacinium nitrate

Structure description

Synthesis and crystallization

Refinement

Structural data

References

organic compounds