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In the structure of the title compound, 4-[3-carboxy-6,8-di­fluoro-1-(2-fluoro­ethyl)-1,4-di­hydro-4-oxo-7-quinolyl]-1-methyl­piperazinium chloride hydrate, C17H19F3N3O3+·­Cl-·­H2O, the quinoline and its substituents, except for the fluoro­ethyl group, are coplanar, while the piperazinium moiety exists in a chair form. There are [pi]-[pi]-stacking interactions between the quinoline rings, and intra- and intermolecular hydrogen bonds in the crystal.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102014968/ta1382sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102014968/ta1382Isup2.hkl
Contains datablock I

CCDC reference: 197331

Comment top

The compound 6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo- quinoline-3-carboxylic acid, the trivial name of which is fleroxacin, is one of the fluoroquinolone antibiotic drugs, and is certified as the best choice for curing infections caused by susceptible bacteria (Drakopoulos & Ioannou, 1997). It affords powerful broad-spectrum antisepsis, long effectiveness, few side effects and no interference with other antibiotics (Weidekamm et al., 1987). It has been widely used for the treatment of bacterial infections, such as those of the respiratory system, the urinary tract, skin, soft tissue, bones and joints, the gastro-intestinal tract and the central nervous system (Krisztina et al., 1990). The photolysis (>320 nm) of fleroxacin results in the loss of the fluorine substituent at C9 (Fig. 1) as fluoride (Martinez et al., 1997). Fleroxacin has the highest DNA photocleaving activity among the fluoroquinolones; DNA damage probably results from the generation of a carbene at C9 as a result of the photoinduced loss of atom F2 as fluoride upon UVA irradiation (Martinez & Chignell, 1998). Therefore, it is important to know the molecular structure of fleroxacin to investigate this reaction better. To this end, the title compound, (I), the hydrochloride hydrate of fleroxacin, has been prepared and its structure is reported here. \sch

The molecular structure of (I) is shown in Fig. 1. The quinoline and its substituents, except the piperazinium moiety and the fluoroethyl group attached to atom N1, are nearly coplanar, with a mean deviation of 0.052 (2) Å, while the quinoline itself is planar, with a mean deviation of 0.032 (2) Å. The piperazinium moiety is in a chair form.

There are three C—F bonds in (I). The C8—F3 bond is apparently longer than the C—F bonds to the quinoline, C11—F1 and C9—F2 (Table 1). This can be attributed to the conjugation of the electrons of atoms F1 and F2 with the quinoline. The C9—F2 bond is longer than C11—F1 and the photoinduced C—F breakage is easier for the former under UV irradiation (Zhang et al., 2000). In the molecule of (I), the nine C—N bonds can be divided into two groups, of which six, falling in the range 1.455 (3)–1.501 (3) Å, characterize C—N single bonds. The two shorter C—N bonds, C5—N1 [1.407 (3) Å] and C6—N1 [1.349 (3) Å], result from the delocalization of their electrons on the quinoline. Another shorter C—N bond, C10—N2 [1.377 (3) Å], arises from the conjugation of the lone pair of electrons on N2 with the quinoline. The bond angles at N1 and N2 are different (Table 1).

In (I), the fleroxacin is in a cationic form, with atom N3 of the piperazinium group being protonated. The C1—O2 and C1—O1 bond lengths (Table 1) of the carboxyl group agree with those found in N,N,N',N'',N''',N'''-triethylenetetraminehexacetic acid (Finnen & Pinkerton, 1997), N-(2-hydroxyethyl)ethylenediaminetriacetic acid (Kettmann et al., 1993) and some derivatives or complexes of betaine (Ilczyszyn, Barnes et al., 1995; Ilczyszyn, Lis & Ratajczak, 1995; Ratajczak et al., 1994), and show that the carboxyl group is in the acid form. The C3—O3 bond length is intermediate between that expected for single and double bonds. The intramolecular hydrogen bond between atoms O1 and O3 (Table 2) may account for this phenomenon.

There are four intermolecular hydrogen bonds in the crystal of (I) (Table 2). The water molecule, as a hydrogen donor, is hydrogen-bonded to the Cl- anion, as well as to the two O atoms of the carboxyl group, forming a three-centre hydrogen bond. In addition, the Cl- anion is also hydrogen-bonded to the protonated N atom of the fleroxacin. Although F is the most electronegative element in (I), no hydrogen bonds were observed around F atoms. The quinoline rings are oriented to give alternate π-π stacking interactions of 3.375 (3) and 3.392 (3) Å (Fig. 2).

Experimental top

Fleroxacin was kindly donated by Qingdao Pharmaceutical Factory. Fleroxacin (0.185 g, 0.5 mmol) was dissolved in distilled water (5 ml) and the pH was adjusted to 5 with dilute hydrochloric acid under heating. The mixture was sealed in a 20 ml stainless-steel reactor with a Teflon liner and heated at 373 K for 76 h. Yellow crystals of (I) were obtained (m.p. 553 K).

Refinement top

The organic H atoms were generated geometrically and allowed to ride on their parent atoms, with N—H = 0.91, O—H = 0.82 and C—H = 0.93–0.97 Å. Are these added distances correct? The water H atoms were located from difference maps and refined with isotropic displacement parameters, which can introduce high Uiso parameters for water H atoms. Therefore, the ratio of Ueq(max)/Ueq(min) is relatively high.

Computing details top

Data collection: SMART (Bruker, Year?); cell refinement: SMART; data reduction: SHELXTL (Sheldrick, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atom-numbering scheme and 50% probability displacement ellipsoids. H atoms are drawn as small spheres of arbitrary radii.
[Figure 2] Fig. 2. A packing diagram for (I) showing the π-π stacking interactions between the quinoline rings of the fleroxacin. All H atoms, lattice water molecules and Cl- anions have been omitted for clarity.
4-[3-carboxy-6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxo-7-quinolyl]- 1-methylpiperazinium chloride hydrate top
Crystal data top
C17H19F3N3O3+·Cl·H2ODx = 1.550 Mg m3
Mr = 423.82Melting point = 552–553 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.961 (8) ÅCell parameters from 7320 reflections
b = 7.979 (5) Åθ = 1.6–25.0°
c = 18.113 (11) ŵ = 0.27 mm1
β = 104.184 (10)°T = 293 K
V = 1816.1 (19) Å3Plate, light yellow
Z = 40.30 × 0.25 × 0.20 mm
F(000) = 880
Data collection top
Make Model CCD area-detector
diffractometer
3209 independent reflections
Radiation source: fine-focus sealed tube2103 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ϕ and ω scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1514
Tmin = 0.923, Tmax = 0.948k = 96
7320 measured reflectionsl = 1921
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.049P)2]
where P = (Fo2 + 2Fc2)/3
3209 reflections(Δ/σ)max = 0.006
263 parametersΔρmax = 0.32 e Å3
3 restraintsΔρmin = 0.22 e Å3
Crystal data top
C17H19F3N3O3+·Cl·H2OV = 1816.1 (19) Å3
Mr = 423.82Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.961 (8) ŵ = 0.27 mm1
b = 7.979 (5) ÅT = 293 K
c = 18.113 (11) Å0.30 × 0.25 × 0.20 mm
β = 104.184 (10)°
Data collection top
Make Model CCD area-detector
diffractometer
3209 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2103 reflections with I > 2σ(I)
Tmin = 0.923, Tmax = 0.948Rint = 0.032
7320 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0383 restraints
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.32 e Å3
3209 reflectionsΔρmin = 0.22 e Å3
263 parameters
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.30649 (10)0.42751 (16)0.03141 (7)0.0480 (4)
F20.20227 (9)0.08553 (15)0.14874 (7)0.0392 (3)
F30.06282 (11)0.33299 (18)0.19962 (8)0.0578 (4)
N10.01656 (13)0.1435 (2)0.07711 (9)0.0287 (4)
N20.36572 (14)0.2335 (2)0.09522 (10)0.0339 (5)
N30.58899 (14)0.2668 (2)0.15901 (10)0.0357 (5)
H3A0.60810.15760.16820.043*
C10.25737 (18)0.2444 (3)0.07653 (13)0.0362 (6)
C20.14409 (17)0.2377 (3)0.03491 (12)0.0306 (5)
C30.06400 (17)0.3163 (3)0.06467 (12)0.0317 (5)
C40.04459 (16)0.2960 (2)0.02017 (11)0.0279 (5)
C50.06800 (16)0.2083 (2)0.04974 (12)0.0264 (5)
C60.11704 (17)0.1594 (3)0.03428 (12)0.0307 (5)
H60.17160.11400.05310.037*
C70.00443 (18)0.0801 (3)0.15613 (12)0.0349 (5)
H7A0.05210.00270.16740.042*
H7B0.06990.02560.15980.042*
C80.02102 (19)0.2194 (3)0.21361 (13)0.0441 (6)
H8A0.03170.17410.26460.053*
H8B0.08600.27550.20990.053*
C90.17591 (17)0.1851 (2)0.08573 (11)0.0283 (5)
C100.25941 (16)0.2518 (2)0.05999 (12)0.0282 (5)
C110.22898 (17)0.3470 (3)0.00770 (12)0.0320 (5)
C120.12699 (17)0.3653 (3)0.04726 (12)0.0324 (5)
H120.11150.42450.09290.039*
C130.44228 (17)0.1808 (3)0.05222 (13)0.0354 (6)
H13A0.41100.19400.00190.042*
H13B0.45970.06340.06210.042*
C140.54216 (17)0.2852 (3)0.07522 (12)0.0372 (6)
H14A0.59320.24850.04740.045*
H14B0.52550.40190.06300.045*
C150.50829 (17)0.3076 (3)0.20329 (13)0.0386 (6)
H15A0.49200.42630.19840.046*
H15B0.53860.28410.25680.046*
C160.40651 (17)0.2090 (3)0.17677 (12)0.0377 (6)
H16A0.42010.09090.18770.045*
H16B0.35440.24680.20350.045*
C170.68666 (18)0.3709 (3)0.18475 (14)0.0481 (7)
H17A0.73720.34140.15600.072*
H17B0.71730.35110.23790.072*
H17C0.66840.48730.17690.072*
Cl0.71815 (6)0.94195 (9)0.16859 (5)0.0677 (3)
O10.27944 (12)0.3331 (2)0.14036 (9)0.0495 (5)
H10.22410.37020.14820.074*
O20.32762 (12)0.1736 (2)0.05476 (9)0.0494 (5)
O30.08495 (12)0.3971 (2)0.12663 (9)0.0475 (5)
O40.52917 (16)0.3095 (2)0.12869 (11)0.0608 (5)
H420.4610 (12)0.261 (3)0.104 (2)0.126 (14)*
H410.5883 (16)0.230 (3)0.138 (2)0.158 (18)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0353 (8)0.0612 (9)0.0485 (9)0.0116 (6)0.0124 (6)0.0168 (7)
F20.0330 (7)0.0490 (8)0.0354 (8)0.0010 (6)0.0078 (6)0.0150 (6)
F30.0535 (10)0.0592 (10)0.0628 (10)0.0079 (7)0.0180 (8)0.0104 (7)
N10.0275 (10)0.0311 (10)0.0282 (11)0.0044 (8)0.0085 (8)0.0006 (8)
N20.0256 (10)0.0527 (12)0.0241 (10)0.0004 (9)0.0075 (8)0.0008 (8)
N30.0291 (11)0.0408 (11)0.0364 (12)0.0020 (8)0.0063 (9)0.0039 (9)
C10.0333 (14)0.0389 (14)0.0353 (15)0.0015 (11)0.0061 (11)0.0080 (11)
C20.0293 (12)0.0318 (12)0.0296 (13)0.0005 (10)0.0050 (10)0.0046 (10)
C30.0336 (13)0.0327 (12)0.0275 (13)0.0006 (10)0.0048 (10)0.0042 (10)
C40.0299 (12)0.0284 (12)0.0249 (12)0.0009 (9)0.0057 (9)0.0018 (9)
C50.0288 (12)0.0242 (11)0.0276 (12)0.0022 (9)0.0094 (9)0.0046 (9)
C60.0279 (13)0.0312 (12)0.0345 (13)0.0037 (9)0.0105 (10)0.0058 (10)
C70.0326 (13)0.0428 (14)0.0319 (13)0.0016 (10)0.0127 (10)0.0076 (10)
C80.0401 (15)0.0616 (17)0.0310 (14)0.0041 (13)0.0092 (11)0.0031 (12)
C90.0320 (13)0.0292 (12)0.0233 (12)0.0004 (9)0.0062 (9)0.0035 (9)
C100.0290 (12)0.0282 (12)0.0269 (12)0.0025 (9)0.0058 (10)0.0040 (9)
C110.0327 (13)0.0341 (13)0.0318 (13)0.0081 (10)0.0130 (10)0.0000 (10)
C120.0349 (14)0.0368 (13)0.0248 (12)0.0022 (10)0.0059 (10)0.0036 (10)
C130.0325 (13)0.0442 (14)0.0306 (13)0.0008 (10)0.0098 (10)0.0035 (10)
C140.0313 (13)0.0505 (15)0.0317 (14)0.0003 (11)0.0112 (10)0.0024 (11)
C150.0343 (13)0.0539 (15)0.0272 (13)0.0046 (11)0.0066 (10)0.0010 (11)
C160.0333 (13)0.0512 (15)0.0292 (13)0.0028 (11)0.0091 (10)0.0043 (11)
C170.0293 (14)0.0618 (17)0.0493 (16)0.0108 (12)0.0025 (11)0.0040 (13)
Cl0.0456 (4)0.0556 (5)0.0988 (6)0.0038 (3)0.0116 (4)0.0026 (4)
O10.0355 (10)0.0679 (12)0.0409 (11)0.0031 (9)0.0014 (8)0.0087 (9)
O20.0295 (10)0.0636 (12)0.0533 (11)0.0059 (8)0.0069 (8)0.0027 (9)
O30.0387 (10)0.0653 (12)0.0351 (10)0.0003 (8)0.0025 (8)0.0152 (8)
O40.0493 (12)0.0639 (13)0.0685 (14)0.0028 (10)0.0131 (10)0.0075 (10)
Geometric parameters (Å, º) top
F1—C111.348 (2)C7—H7A0.9700
F2—C91.364 (2)C7—H7B0.9700
F3—C81.390 (3)C8—H8A0.9700
N1—C61.349 (3)C8—H8B0.9700
N1—C51.407 (3)C9—C101.385 (3)
N1—C71.490 (3)C10—C111.414 (3)
N2—C101.377 (3)C11—C121.348 (3)
N2—C161.455 (3)C12—H120.9300
N2—C131.465 (3)C13—C141.509 (3)
N3—C171.490 (3)C13—H13A0.9700
N3—C141.497 (3)C13—H13B0.9700
N3—C151.501 (3)C14—H14A0.9700
N3—H3A0.9100C14—H14B0.9700
C1—O21.216 (3)C15—C161.509 (3)
C1—O11.326 (3)C15—H15A0.9700
C1—C21.478 (3)C15—H15B0.9700
C2—C61.367 (3)C16—H16A0.9700
C2—C31.427 (3)C16—H16B0.9700
C3—O31.265 (3)C17—H17A0.9600
C3—C41.449 (3)C17—H17B0.9600
C4—C121.394 (3)C17—H17C0.9600
C4—C51.413 (3)O1—H10.8200
C5—C91.403 (3)O4—H420.969 (10)
C6—H60.9300O4—H410.980 (10)
C7—C81.504 (3)
C6—N1—C5119.25 (18)F2—C9—C5118.85 (18)
C6—N1—C7116.37 (18)C10—C9—C5124.41 (19)
C5—N1—C7123.74 (17)N2—C10—C9125.38 (19)
C10—N2—C16123.92 (18)N2—C10—C11119.58 (19)
C10—N2—C13121.02 (18)C9—C10—C11115.04 (18)
C16—N2—C13112.10 (17)F1—C11—C12119.3 (2)
C17—N3—C14111.39 (17)F1—C11—C10117.45 (18)
C17—N3—C15111.20 (18)C12—C11—C10123.2 (2)
C14—N3—C15110.97 (17)C11—C12—C4120.4 (2)
C17—N3—H3A107.7C11—C12—H12119.8
C14—N3—H3A107.7C4—C12—H12119.8
C15—N3—H3A107.7N2—C13—C14109.99 (18)
O2—C1—O1120.8 (2)N2—C13—H13A109.7
O2—C1—C2123.1 (2)C14—C13—H13A109.7
O1—C1—C2116.1 (2)N2—C13—H13B109.7
C6—C2—C3120.0 (2)C14—C13—H13B109.7
C6—C2—C1118.9 (2)H13A—C13—H13B108.2
C3—C2—C1121.0 (2)N3—C14—C13109.45 (18)
O3—C3—C2122.8 (2)N3—C14—H14A109.8
O3—C3—C4121.2 (2)C13—C14—H14A109.8
C2—C3—C4115.96 (19)N3—C14—H14B109.8
C12—C4—C5119.80 (19)C13—C14—H14B109.8
C12—C4—C3118.88 (19)H14A—C14—H14B108.2
C5—C4—C3121.3 (2)N3—C15—C16112.71 (19)
C9—C5—N1124.17 (19)N3—C15—H15A109.0
C9—C5—C4116.90 (19)C16—C15—H15A109.0
N1—C5—C4118.86 (18)N3—C15—H15B109.0
N1—C6—C2124.4 (2)C16—C15—H15B109.0
N1—C6—H6117.8H15A—C15—H15B107.8
C2—C6—H6117.8N2—C16—C15108.96 (18)
N1—C7—C8111.55 (18)N2—C16—H16A109.9
N1—C7—H7A109.3C15—C16—H16A109.9
C8—C7—H7A109.3N2—C16—H16B109.9
N1—C7—H7B109.3C15—C16—H16B109.9
C8—C7—H7B109.3H16A—C16—H16B108.3
H7A—C7—H7B108.0N3—C17—H17A109.5
F3—C8—C7109.08 (18)N3—C17—H17B109.5
F3—C8—H8A109.9H17A—C17—H17B109.5
C7—C8—H8A109.9N3—C17—H17C109.5
F3—C8—H8B109.9H17A—C17—H17C109.5
C7—C8—H8B109.9H17B—C17—H17C109.5
H8A—C8—H8B108.3C1—O1—H1109.5
F2—C9—C10116.70 (18)H42—O4—H41113.9 (15)
O2—C1—C2—C65.2 (3)N1—C5—C9—C10178.45 (19)
O1—C1—C2—C6174.9 (2)C4—C5—C9—C104.6 (3)
O2—C1—C2—C3177.0 (2)C16—N2—C10—C928.1 (3)
O1—C1—C2—C32.8 (3)C13—N2—C10—C9130.9 (2)
C6—C2—C3—O3176.7 (2)C16—N2—C10—C11151.1 (2)
C1—C2—C3—O31.1 (3)C13—N2—C10—C1149.9 (3)
C6—C2—C3—C44.4 (3)F2—C9—C10—N24.0 (3)
C1—C2—C3—C4177.83 (19)C5—C9—C10—N2178.60 (19)
O3—C3—C4—C120.9 (3)F2—C9—C10—C11176.79 (17)
C2—C3—C4—C12178.02 (19)C5—C9—C10—C110.7 (3)
O3—C3—C4—C5178.87 (19)N2—C10—C11—F15.3 (3)
C2—C3—C4—C52.2 (3)C9—C10—C11—F1174.02 (18)
C6—N1—C5—C9173.59 (19)N2—C10—C11—C12177.3 (2)
C7—N1—C5—C915.9 (3)C9—C10—C11—C123.4 (3)
C6—N1—C5—C43.3 (3)F1—C11—C12—C4174.13 (19)
C7—N1—C5—C4167.17 (18)C10—C11—C12—C43.3 (3)
C12—C4—C5—C94.7 (3)C5—C4—C12—C111.0 (3)
C3—C4—C5—C9175.53 (18)C3—C4—C12—C11179.2 (2)
C12—C4—C5—N1178.18 (18)C10—N2—C13—C14136.7 (2)
C3—C4—C5—N11.6 (3)C16—N2—C13—C1462.0 (2)
C5—N1—C6—C21.1 (3)C17—N3—C14—C13178.69 (19)
C7—N1—C6—C2170.08 (19)C15—N3—C14—C1354.2 (2)
C3—C2—C6—N13.0 (3)N2—C13—C14—N358.3 (2)
C1—C2—C6—N1179.24 (19)C17—N3—C15—C16177.85 (18)
C6—N1—C7—C8102.7 (2)C14—N3—C15—C1653.3 (2)
C5—N1—C7—C868.0 (3)C10—N2—C16—C15140.8 (2)
N1—C7—C8—F362.1 (2)C13—N2—C16—C1558.6 (2)
N1—C5—C9—F24.2 (3)N3—C15—C16—N254.1 (3)
C4—C5—C9—F2172.79 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···Cli0.912.233.067 (3)152
O1—H1···O30.821.762.524 (3)154
O4—H42···O20.97 (2)1.87 (2)2.842 (3)178 (1)
O4—H42···O10.97 (2)2.66 (2)3.300 (3)124 (1)
O4—H41···Clii0.98 (2)2.13 (2)3.111 (3)176 (1)
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC17H19F3N3O3+·Cl·H2O
Mr423.82
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)12.961 (8), 7.979 (5), 18.113 (11)
β (°) 104.184 (10)
V3)1816.1 (19)
Z4
Radiation typeMo Kα
µ (mm1)0.27
Crystal size (mm)0.30 × 0.25 × 0.20
Data collection
DiffractometerMake Model CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.923, 0.948
No. of measured, independent and
observed [I > 2σ(I)] reflections
7320, 3209, 2103
Rint0.032
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.100, 1.01
No. of reflections3209
No. of parameters263
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.32, 0.22

Computer programs: SMART (Bruker, Year?), SMART, SHELXTL (Sheldrick, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL.

Selected geometric parameters (Å, º) top
F1—C111.348 (2)N2—C131.465 (3)
F2—C91.364 (2)N3—C171.490 (3)
F3—C81.390 (3)N3—C141.497 (3)
N1—C61.349 (3)N3—C151.501 (3)
N1—C51.407 (3)C1—O21.216 (3)
N1—C71.490 (3)C1—O11.326 (3)
N2—C101.377 (3)C3—O31.265 (3)
N2—C161.455 (3)
C6—N1—C5119.25 (18)C17—N3—C14111.39 (17)
C6—N1—C7116.37 (18)C17—N3—C15111.20 (18)
C5—N1—C7123.74 (17)C14—N3—C15110.97 (17)
C10—N2—C16123.92 (18)O2—C1—O1120.8 (2)
C10—N2—C13121.02 (18)O2—C1—C2123.1 (2)
C16—N2—C13112.10 (17)O1—C1—C2116.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···Cli0.912.2343.067 (3)152
O1—H1···O30.821.7622.524 (3)154
O4—H42···O20.97 (2)1.87 (2)2.842 (3)178.11 (18)
O4—H42···O10.97 (2)2.66 (2)3.300 (3)123.94 (18)
O4—H41···Clii0.98 (2)2.13 (2)3.111 (3)175.55 (17)
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z.
 

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