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Moxifloxacin, a novel fluoro­quinolone with a broad spectrum of anti­bacterial activity, is available as the solvated monohydro­chloride salt 7-[(S,S)-2-aza-8-azoniabicyclo­[4.3.0]non-8-yl]-1-cyclo­propyl-6-fluoro-8-meth­oxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid chloride–water–methanol (2/1/1), C21H25FN3O4+·Cl·0.5H2O·0.5CH3OH. The asymmetric unit contains two cations, two chloride ions, a mol­ecule of water and one methanol mol­ecule. The two cations adopt conformations that differ by an almost 180° rotation with respect to the piperidinopyrrolidine side chain. The cyclo­propyl ring and the meth­oxy group are not coplanar with the quinoline ring system. The carboxylic acid function, the protonated terminal piperidyl N atom, the water mol­ecule, the chloride ion and the methanol mol­ecule participate in O—H...O, O—H...Cl, N—H...O and N—H...Cl hydrogen bonding, linking the mol­ecules into extended two-dimensional networks.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106022256/ln3009sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106022256/ln3009Isup2.hkl
Contains datablock I

CCDC reference: 618624

Comment top

Development of resistance to antimicrobial agents and the emergence of multiresistant pathogens have generated worldwide concern in the medicinal community. The fluoroquinolone class of antimicrobial agents is being used empirically in an increasing number of patients because of the resistance developed to the more traditional antimicrobial agents. Fluoroquinolones are active against a wide range of multiresistant pathogens, as they act against different molecular targets compared with other antimicrobial agents (Hooper, 2000). All fluoroquinolones are analogues of the basic quinoline pharmacore (Fig. 1), and distinct antimicrobial and pharmacological activities have been defined for each modification in the molecular structure (Domagala, 1994; Tillotson, 1996).

Moxifloxacin is a novel third-generation fluoroquinolone, the antimicrobial activity of which depends upon inhibition of DNA gyrase (bacterial topoisomerase II), an enzyme necessary for DNA replication, transcription, repair and recombination (von Keutz & Schluter, 1999). Moxifloxacin, a chiral (S,S)-8-methoxyfluoroquinolone derivative formulated as a hydrochloride salt, is supplied as a film-covered tablet, Avelox, developed by Bayer Pharmaceuticals Corporation and marketed in the United States by Schering–Plough. Moxifloxacin is the only topical fluroquinolone without added preservatives and is formulated at a physiological pH of 6.8 compared with 6.0 for gatifloxacin. Moxifloxacin is highly effective against Gram-positive organisms, has better pharmacokinetic properties and has no precipitates. Because moxifloxacin is self-preserved, it has minimal toxicity and is safe and effective for children, including newborns. Recently the US Food and Drug Administration (FDA) has approved the once-daily antibiotic Avelox for the treatment of complicated skin and skin structure infections in adults caused by methicillin-susceptible Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae or Enterobacter cloacae. In a continuation of our ongoing programmes on the structural elucidation of drug molecules and to gain further insight into structure–activity relationships, the crystal structure of moxifloxacin hydrochloride–water–methanol (2/1/1), (I), was carried out and is reported here.

The bond distances and angles in (I) are in normal ranges (Allen et al., 1987) and are comparable to the corresponding values observed in similar compounds (Sivalakshmidevi et al., 2000; Prasanna & Guru Row, 2001; Sun et al., 2004; Li et al., 2005). The asymmetric unit consists of two independent moxifloxacin cations (unprimed and primed atoms in Fig. 2) protonated at the terminal piperazinyl N atom, two chloride anions, one water molecule and one methanol molecule. The conformations of the two cations differ principally by a rotation of the piperidinopyrrolidine ring system about the C7—N2 bond by nearly 180°. If one ignores the uniqueness in the configuration of the piperidinopyrrolidine ring system introduced by the presence of atom N3, the skeletons of two symmetry-independent cations appear to be related by a pseudo centre of inversion. After inversion of primed molecule, the r.m.s. deviation for superimposing the quinoline moieties in the asymmetric unit is 0.025 Å (Fig. 3).

An earlier study indicated that substitution at the N1 position is important for antibacterial activity (Albrecht, 1977). The cyclopropyl group is by far the optimal group because of its favorable combination of steric, spatial and through space electronic interactions (Chu & Fernandes, 1989). The orientation of the plane of the N1 cyclopropyl ring is practically perpendicular to that of the quinoline system [C1—N1—C11—C12 and C1—N1—C11—C13 are −113.7 (4) and −43.3 (5)° for the unprimed cation, and 116.0 (4) and 48.6 (6)° for the primed cation, respectively]. The quinoline ring system is essentially planar and the dihedral angles between the planes of the cyclopropyl and quinoline ring systems are 69.6 (2) and 71.1 (2)° for the unprimed and primed cations, respectively. The corresponding angles are 56.2° in 2-hydroxyethanaminium enrofloxacin (Sun et al., 2004), 60.8° in sparfloxacin (Miyamoto et al., 1990), 78.8 and 70.9° in sitafloxacin sesquihydrate (Suzuki et al., 2000), 56.0° in ciprofloxacin HCl (Turel & Golobic, 2003), and 56.5 and 54.6° in ciprofloxacin lactate (Prasanna & Guru Row, 2001).

The positions of the substituents at atoms C2 and C3, having an interaction between the carboxylic acid group and the carbonyl group, are generally considered necessary for the binding of quinolones to DNA gyrase (Schentag & Domagala, 1985). The carboxylic acid group O1 forms an intramolecular hydrogen bond with the carbonyl group O3. This hydrogen bond forms a quasi-six-membered ring. The planarity between the 3-carbonyl group and the carboxylic acid group is reflected by the C3—C2—C10—O1 and C10—C2—C3—O3 torsion angles of 2.8 (6) and −1.3 (6)° for the unprimed cation, and −4.3 (6) and 1.2 (6)° for the primed cation, respectively.

An analysis of quinolones, using an automated computer structure evaluation program, concluded that cell permeability is predominantly controlled by the nature of the C7 substituent (Klopman et al., 1987). The nature of the C7 substituent is known to influence quinoline activity in Gram-positive and Gram-negative bacteria (Bryskier & Chantot, 1995) and also the target preference of fluoroquinolones (Alovero et al., 2000). The most common C7 substituents are substituted piperazin-1-yl (norfloxacin, ciprofloxacin, enrofloxacin, perfloxacin, ofloxacin, difloxacin, fleroxacin and amifloxacin). The title compound, moxifloxacin, has the bulkiest C7 substituent, a bicyclic fused ring composed of a pyrrolidine and piperazine ring, of the currently available fluoroquinolone agents, which prevents active efflux associated with the NorA or pmrA genes seen in certain Gram-positive bacteria (Blondeau, 1999; Pestova et al., 2000). An important aspect of the title compound is the orientation of its piperidinopyrrolidine side chain. In the unprimed cation, it is rotated so that atom C15 is facing away from the F atom to give a transoid arrangement [C6—C7—N2—C15 = 152.9 (4)°], while in the primed cation, this relationship is cisoid and the corresponding torsion angle is 17.3 (6)°. It is thus almost as if the piperidinopyrrolidine ring in the unprimed cation has been rotated by 180° to yield the primed cation. This arrangement is further supported by the N2—C15—C16—N3 torsion angle of −154.9 (3)° in the unprimed cation and −84.1 (4)° in the primed cation, perhaps providing the accessibility of the piperazinium N atom to hydrogen bonding. This conformational arrangement may be contributing to the different modes of hydrogen bonding in the cations. The orientation of the piperazine ring, a least substituent [clarify?] at C7, has a C6—C7—N2—C15 torsion angle of 67.4° in ciprofloxacin HCl, 58.9 (2)° in 2-hydroxethanaminium enrofloxacin, 3.4 and 35.8° in sitafloxacin sesquihydrate, and −73.3 (7)° in sparfloxacin. Atoms N3 and O2, which occupy the two terminal positions of the cation in the title compound, are separated by distances of 11.722 (5) and 11.467 (5) Å for the unprimed and primed cations, respectively. The corresponding distances found in similar antibacterial agents are 11.23 Å (ciprofloxacin HCl), 11.49 and 11.33 Å (ciprofloxacin lactate), 11.39 Å (2-hydroxethanaminium enrofloxacin), 10.83 and 10.99 Å (sitafloxacin sesquihydrate), and 11.23 Å (sparfloxacin). The piperazinium ring in (I) adopts a chair conformation with the exposed N atom participating in the hydrogen bonding interactions. The pyrrolidine ring favors a half-chair conformation twisted on atoms C16—C20 for both the cations. An overlay (Fig. 4) of the title compound with other similar antibacterial agents, by superimposing the quinoline systems, significantly reveals the conformational similarities.

The methoxy group on atom C8 in moxifloxacin is thought to contribute to enhanced activity and lower selection of resistant mutants of Gram-positive bacteria compared with the C8-unsubstituted analogue (Marutani et al., 1993). The C14/O4 methoxy group is almost perpendicular to the plane of the quinoline ring system [C14—O4—C8—C9 = 95.4 (4) and −80.2 (4)° for the unprimed and primed cations, respectively].

Different modes of hydrogen-bonding interactions, viz. cation–cation, cation–water, cation–chloride ion, methanol–chloride ion and water–chloride ion, stabilize the molecules in the crystal structure (Table 1 and Fig.). The two H atoms at atom N3' of the piperazine ring in the primed cation participate in hydrogen bonding with chloride ions, while, in the unprimed cation, they participate in hydrogen bonding with one chloride ion and with a water molecule. The water molecule acts as a donor in hydrogen bonds with a chloride ion and the carbonyl O atom of the carboxylic acid group of the unprimed cation. The methanol molecule forms a hydrogen bond with a chloride ion. Taken together, the hydrogen bonds link all of the components of the structutre into extended two-dimensional networks which lie parallel to the (101) plane.

The crystal structure of (I) may be viewed in the context of a molecular model for the quinoline–gyrase–DNA complex proposed by Shen et al. (1989). According to this model, substituents on atoms N1 and C8 are envisaged as providing the necessary hydrophobic interactions. Binding to DNA is suggested through a hydrogen-bonding domain on the drug comprising the C2 carboxylic acid group and the carbonyl group at C3, while the substituent on atom C7 is involved in drug-enzyme interactions. In (I), the perpendicular orientation of the planes of the cyclopropyl and the methoxy groups with respect to that of the quinoline skeleton may possibly be providing the hydrophobic interactions. The coplanar arrangement between the carboxylic acid group and the carbonyl group – the hydrogen-bonding domain of the drug – may be facilitating the required binding to DNA. Despite the presence of a bulky bicyclic fused ring substituent on atom C7, the drug-enzyme interaction is possible through the cationic terminal piperazine N atom.

Experimental top

To obtain crystals suitable for X-ray studies, moxifloxacin hydrochloride (Neuland Laboratories Ltd, Hyderabad) was dissolved in a methanol–water solution (80:20)(quantities of reagents?) and the solution was allowed to evaporate slowly.

Refinement top

All O– and N-bound H atoms were located in a difference electron density map and refined with O—H bond-length restraints of 0.82 (2) Å (water molecule) and 0.92 (2) Å (carboxylic acid and methanol), and N—H bond-length restraints of 0.90 (2) Å. The H atoms attached to C atoms were positioned geometrically and refined as riding atoms [aromatic C—H = 0.93 Å, methine C—H = 0.98 Å and methylene C—H = 0.97 Å with Uiso(H) = 1.2Ueq(parent C atom), and methyl C—H = 0.96 Å, with Uiso(H) = 1.5Ueq(parent methyl C atom)]. The methyl groups were allowed to rotate but not to tip. The absolute configuration of the procured material was known in advance and was confirmed by unambiguous refinement of the absolute structure parameter (Flack & Bernardinelli, 2000).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. Structural modifications of fluoroquinolones.
[Figure 2] Fig. 2. The asymmetric unit of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. Hydrogen bonds are shown as a dashed line.
[Figure 3] Fig. 3. The least-squares fit between the skeletons of the two independent cations in (I) (above) and with the primed cation inverted (below). The quinolone ring system was fitted and H atoms were omitted for clarity.
[Figure 4] Fig. 4. An overlay of the skeletons of some antibacterial molecules, viz. the primed cation of (I) (labelled 1), ciprofloxacin HCl (labelled 2), 2-hydroxyethanaminium enrofloxacin (labelled 3) and sitafloxacin sesquihydrate (labelled 4).
[Figure 5] Fig. 5. A part of the crystal packing of (I), with extracellular molecules to illustrate the water–chloride ion–methanol network (dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity.
7-[(S,S)-8-azonia-2-azabicylo[4.3.0]non-8-yl]-1-cyclopropyl-6-fluoro-8-methoxy- 4-oxo-1,4-dihydro-3-quinoline-3-carboxylic acid chloride–water–methanol (2/1/1) top
Crystal data top
C21H25FN3O4+·Cl·0.5H2O·0.5CH4OF(000) = 976
Mr = 462.92Dx = 1.402 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4075 reflections
a = 6.828 (2) Åθ = 2.4–24.4°
b = 20.929 (6) ŵ = 0.22 mm1
c = 15.357 (5) ÅT = 273 K
β = 92.007 (5)°Block, colorless
V = 2193.4 (11) Å30.21 × 0.19 × 0.09 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5008 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.076
Graphite monochromatorθmax = 25.0°, θmin = 1.7°
ω scanh = 88
19500 measured reflectionsk = 2424
7616 independent reflectionsl = 1818
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.104 w = 1/[σ2(Fo2) + (0.0384P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.90(Δ/σ)max < 0.001
7616 reflectionsΔρmax = 0.26 e Å3
607 parametersΔρmin = 0.24 e Å3
8 restraintsAbsolute structure: Flack & Bernardinelli (2000), 3643 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.12 (6)
Crystal data top
C21H25FN3O4+·Cl·0.5H2O·0.5CH4OV = 2193.4 (11) Å3
Mr = 462.92Z = 4
Monoclinic, P21Mo Kα radiation
a = 6.828 (2) ŵ = 0.22 mm1
b = 20.929 (6) ÅT = 273 K
c = 15.357 (5) Å0.21 × 0.19 × 0.09 mm
β = 92.007 (5)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5008 reflections with I > 2σ(I)
19500 measured reflectionsRint = 0.076
7616 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.104Δρmax = 0.26 e Å3
S = 0.90Δρmin = 0.24 e Å3
7616 reflectionsAbsolute structure: Flack & Bernardinelli (2000), 3643 Friedel pairs
607 parametersAbsolute structure parameter: 0.12 (6)
8 restraints
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
Cl11.41424 (17)0.73383 (5)0.87896 (7)0.0568 (3)
F10.7688 (4)0.59029 (9)0.47046 (14)0.0550 (6)
N10.8146 (5)0.85417 (13)0.4752 (2)0.0387 (8)
N20.8482 (5)0.65135 (12)0.63265 (19)0.0367 (8)
N31.0820 (6)0.63094 (16)0.8496 (2)0.0421 (9)
H311.143 (5)0.5969 (13)0.876 (2)0.048 (11)*
H321.178 (5)0.6617 (17)0.854 (3)0.077 (16)*
O10.6622 (5)0.86456 (18)0.17065 (19)0.0610 (9)
H20.664 (9)0.821 (3)0.180 (4)0.13 (3)*
O20.7133 (5)0.95498 (15)0.24351 (19)0.0724 (10)
O30.6897 (4)0.75971 (13)0.24631 (17)0.0507 (8)
O40.7979 (4)0.78401 (10)0.63448 (15)0.0356 (6)
C10.7777 (6)0.88575 (18)0.4002 (2)0.0392 (10)
H10.78480.93010.40140.047*
C20.7311 (6)0.85743 (18)0.3232 (2)0.0406 (10)
C30.7235 (6)0.78856 (19)0.3168 (2)0.0379 (10)
C40.7543 (5)0.75464 (17)0.3985 (2)0.0347 (9)
C50.7401 (5)0.68779 (17)0.4003 (2)0.0352 (9)
H50.70690.66570.34940.042*
C60.7738 (6)0.65535 (16)0.4747 (2)0.0364 (10)
C70.8126 (5)0.68434 (17)0.5567 (2)0.0335 (9)
C80.8052 (5)0.75193 (16)0.5564 (2)0.0314 (9)
C90.7930 (6)0.78688 (16)0.4781 (2)0.0315 (9)
C100.7023 (6)0.8968 (2)0.2434 (3)0.0491 (11)
C110.9027 (6)0.88992 (16)0.5486 (2)0.0412 (10)
H110.81240.90380.59310.049*
C121.1027 (7)0.87392 (18)0.5803 (2)0.0502 (12)
H12A1.17030.83970.55110.060*
H12B1.13220.87720.64230.060*
C131.0648 (7)0.93435 (18)0.5307 (3)0.0571 (13)
H13A1.07110.97430.56280.069*
H13B1.10920.93670.47150.069*
C140.6032 (7)0.7858 (2)0.6679 (3)0.0638 (14)
H14A0.51300.80160.62370.096*
H14B0.60210.81340.71780.096*
H14C0.56500.74350.68460.096*
C150.9668 (6)0.67783 (17)0.7060 (2)0.0411 (10)
H15A0.88870.70520.74210.049*
H15B1.07720.70200.68540.049*
C161.0352 (6)0.61856 (16)0.7556 (2)0.0370 (9)
H16A1.15280.60190.72860.044*
C170.9103 (7)0.64361 (19)0.9044 (3)0.0473 (11)
H17A0.85090.68410.88760.057*
H17B0.95360.64650.96510.057*
C180.7610 (6)0.5909 (2)0.8936 (3)0.0510 (11)
H18A0.64820.60050.92790.061*
H18B0.81730.55100.91460.061*
C190.6964 (6)0.58380 (18)0.7983 (3)0.0487 (11)
H19A0.62970.62250.77910.058*
H19B0.60410.54870.79250.058*
C200.8692 (6)0.57125 (16)0.7400 (2)0.0407 (10)
H200.91780.52770.74960.049*
C210.8222 (6)0.58149 (16)0.6434 (2)0.0426 (10)
H21A0.91180.55780.60790.051*
H21B0.68890.56870.62810.051*
Cl1'0.53502 (18)0.99402 (5)0.08788 (7)0.0581 (3)
F1'0.2205 (4)0.89775 (9)0.25966 (14)0.0569 (7)
N1'0.1663 (5)0.63539 (13)0.27991 (19)0.0399 (8)
N2'0.1515 (5)0.82742 (13)0.10228 (19)0.0379 (8)
N3'0.2661 (6)0.87774 (15)0.0749 (2)0.0431 (9)
H330.370 (4)0.9048 (15)0.073 (2)0.047 (12)*
H340.318 (6)0.8395 (12)0.063 (2)0.062 (14)*
O1'0.3398 (5)0.63504 (17)0.58378 (19)0.0582 (9)
H2'0.328 (6)0.6759 (19)0.567 (3)0.053 (14)*
O2'0.2748 (5)0.54367 (15)0.5169 (2)0.0731 (11)
O3'0.3085 (4)0.73922 (13)0.49950 (15)0.0466 (7)
O4'0.1927 (4)0.69722 (11)0.11411 (15)0.0406 (7)
C1'0.2027 (6)0.60754 (17)0.3575 (2)0.0441 (11)
H1'0.18840.56340.36040.053*
C2'0.2586 (6)0.63809 (18)0.4321 (2)0.0396 (10)
C3'0.2693 (5)0.70751 (17)0.4314 (2)0.0352 (9)
C4'0.2360 (5)0.73714 (17)0.3473 (2)0.0343 (9)
C5'0.2498 (6)0.80434 (17)0.3400 (2)0.0360 (10)
H5'0.28120.82900.38880.043*
C6'0.2169 (6)0.83275 (16)0.2611 (2)0.0390 (10)
C7'0.1831 (6)0.79915 (16)0.1824 (2)0.0357 (9)
C8'0.1863 (6)0.73200 (17)0.1905 (2)0.0360 (9)
C9'0.1945 (6)0.70168 (16)0.2712 (2)0.0362 (10)
C10'0.2892 (6)0.6012 (2)0.5132 (3)0.0476 (11)
C11'0.0797 (7)0.59638 (18)0.2089 (3)0.0550 (12)
H11'0.16940.57730.16770.066*
C12'0.1182 (7)0.6143 (2)0.1750 (3)0.0671 (14)
H12C0.14900.60670.11370.080*
H12D0.17760.65230.19870.080*
C13'0.0956 (9)0.5576 (2)0.2330 (3)0.087 (2)
H13C0.11170.51560.20690.104*
H13D0.14030.56120.29200.104*
C14'0.3876 (7)0.6788 (2)0.0937 (3)0.0642 (14)
H14D0.46510.71630.08460.096*
H14E0.38370.65330.04170.096*
H14F0.44480.65440.14100.096*
C15'0.1996 (7)0.89435 (16)0.0820 (2)0.0450 (11)
H15C0.33990.90170.08610.054*
H15D0.13510.92370.12060.054*
C16'0.1214 (6)0.90113 (16)0.0104 (2)0.0427 (11)
H16'0.08740.94580.02250.051*
C17'0.1800 (7)0.87481 (19)0.1651 (2)0.0551 (13)
H17C0.27860.86030.20460.066*
H17D0.13810.91720.18340.066*
C18'0.0089 (7)0.8303 (2)0.1698 (3)0.0560 (13)
H18C0.05390.78710.15760.067*
H18D0.04900.83090.22840.067*
C19'0.1456 (7)0.8483 (2)0.1057 (3)0.0543 (12)
H19C0.21240.88670.12620.065*
H19D0.24190.81430.10380.065*
C20'0.0622 (6)0.86004 (18)0.0146 (2)0.0421 (10)
H20'0.16270.88150.01880.051*
C21'0.0093 (6)0.80120 (16)0.0377 (2)0.0409 (10)
H21C0.09860.78060.06610.049*
H21D0.07120.77050.00020.049*
O50.6689 (6)0.96216 (18)0.2814 (3)0.0882 (12)
H510.627 (12)0.968 (4)0.224 (2)0.21 (4)*
C220.5020 (9)0.9743 (3)0.3316 (4)0.098 (2)
H22A0.45211.01580.31750.146*
H22B0.40490.94250.32030.146*
H22C0.53260.97320.39220.146*
O1W1.2256 (6)0.51760 (16)0.9136 (3)0.0694 (10)
H1W1.259 (8)0.500 (2)0.870 (2)0.09 (2)*
H2W1.300 (7)0.514 (3)0.958 (2)0.10 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0600 (8)0.0446 (6)0.0665 (8)0.0054 (5)0.0125 (6)0.0003 (5)
F10.0856 (19)0.0303 (12)0.0488 (14)0.0005 (12)0.0011 (12)0.0070 (10)
N10.046 (2)0.0314 (17)0.039 (2)0.0022 (15)0.0023 (15)0.0033 (15)
N20.051 (2)0.0249 (15)0.0333 (19)0.0032 (14)0.0076 (16)0.0013 (14)
N30.053 (3)0.0335 (19)0.039 (2)0.0003 (18)0.0045 (18)0.0076 (16)
O10.076 (3)0.072 (2)0.0354 (19)0.0051 (18)0.0005 (15)0.0124 (17)
O20.107 (3)0.058 (2)0.051 (2)0.0012 (19)0.0078 (19)0.0192 (16)
O30.061 (2)0.0627 (18)0.0282 (16)0.0031 (15)0.0001 (14)0.0052 (14)
O40.0505 (19)0.0310 (13)0.0255 (14)0.0024 (12)0.0042 (13)0.0026 (11)
C10.042 (3)0.037 (2)0.039 (2)0.0014 (18)0.002 (2)0.0095 (18)
C20.042 (3)0.047 (2)0.032 (2)0.0018 (19)0.0005 (19)0.0072 (19)
C30.031 (3)0.055 (3)0.028 (2)0.0078 (19)0.0031 (18)0.0021 (19)
C40.030 (2)0.041 (2)0.033 (2)0.0016 (17)0.0011 (18)0.0021 (17)
C50.036 (3)0.042 (2)0.027 (2)0.0023 (17)0.0000 (18)0.0071 (17)
C60.043 (3)0.030 (2)0.036 (2)0.0023 (17)0.004 (2)0.0065 (18)
C70.025 (2)0.039 (2)0.037 (2)0.0011 (17)0.0017 (18)0.0005 (18)
C80.035 (2)0.035 (2)0.024 (2)0.0013 (16)0.0002 (17)0.0005 (16)
C90.031 (2)0.0310 (19)0.033 (2)0.0010 (16)0.0060 (17)0.0021 (16)
C100.050 (3)0.062 (3)0.035 (3)0.002 (2)0.007 (2)0.008 (2)
C110.060 (3)0.031 (2)0.032 (2)0.004 (2)0.002 (2)0.0019 (17)
C120.070 (4)0.039 (2)0.041 (3)0.009 (2)0.014 (2)0.0026 (19)
C130.084 (4)0.034 (2)0.052 (3)0.014 (2)0.010 (3)0.000 (2)
C140.074 (4)0.073 (3)0.046 (3)0.005 (3)0.013 (3)0.021 (2)
C150.047 (3)0.034 (2)0.041 (2)0.0068 (19)0.005 (2)0.0062 (18)
C160.045 (3)0.0337 (19)0.032 (2)0.0013 (18)0.0002 (18)0.0048 (17)
C170.068 (3)0.042 (2)0.032 (2)0.002 (2)0.009 (2)0.0015 (18)
C180.052 (3)0.054 (3)0.048 (3)0.002 (2)0.012 (2)0.013 (2)
C190.054 (3)0.039 (2)0.054 (3)0.009 (2)0.006 (2)0.004 (2)
C200.056 (3)0.0245 (19)0.041 (3)0.0015 (18)0.002 (2)0.0044 (17)
C210.054 (3)0.0262 (19)0.048 (3)0.0009 (18)0.001 (2)0.0010 (18)
Cl1'0.0760 (9)0.0453 (6)0.0524 (7)0.0178 (6)0.0055 (6)0.0041 (5)
F1'0.099 (2)0.0281 (12)0.0432 (14)0.0032 (12)0.0012 (13)0.0055 (10)
N1'0.055 (2)0.0297 (17)0.035 (2)0.0058 (15)0.0021 (16)0.0018 (14)
N2'0.053 (2)0.0277 (16)0.0319 (19)0.0022 (15)0.0066 (16)0.0017 (14)
N3'0.051 (3)0.0283 (19)0.050 (2)0.0077 (18)0.0042 (18)0.0012 (16)
O1'0.063 (2)0.067 (2)0.044 (2)0.0010 (18)0.0032 (15)0.0114 (17)
O2'0.102 (3)0.053 (2)0.064 (2)0.0060 (18)0.010 (2)0.0196 (17)
O3'0.053 (2)0.0562 (17)0.0307 (16)0.0008 (15)0.0001 (13)0.0041 (14)
O4'0.059 (2)0.0306 (13)0.0320 (16)0.0087 (13)0.0037 (13)0.0054 (11)
C1'0.056 (3)0.032 (2)0.045 (3)0.0002 (19)0.002 (2)0.0094 (19)
C2'0.035 (3)0.046 (2)0.038 (2)0.0007 (18)0.0004 (19)0.0123 (19)
C3'0.027 (2)0.045 (2)0.034 (2)0.0004 (17)0.0020 (18)0.0005 (19)
C4'0.033 (2)0.037 (2)0.033 (2)0.0020 (18)0.0090 (18)0.0001 (17)
C5'0.039 (3)0.038 (2)0.031 (2)0.0047 (17)0.0028 (18)0.0108 (17)
C6'0.052 (3)0.0232 (19)0.041 (3)0.0005 (17)0.001 (2)0.0062 (17)
C7'0.043 (3)0.0288 (19)0.035 (2)0.0010 (17)0.0012 (19)0.0008 (16)
C8'0.045 (3)0.0305 (19)0.033 (2)0.0008 (18)0.0008 (18)0.0059 (18)
C9'0.042 (3)0.0265 (19)0.040 (2)0.0016 (17)0.0009 (19)0.0023 (17)
C10'0.048 (3)0.051 (3)0.043 (3)0.003 (2)0.001 (2)0.004 (2)
C11'0.079 (4)0.031 (2)0.054 (3)0.011 (2)0.003 (3)0.004 (2)
C12'0.074 (4)0.075 (3)0.051 (3)0.031 (3)0.012 (3)0.001 (3)
C13'0.137 (6)0.062 (3)0.061 (4)0.055 (3)0.010 (3)0.006 (3)
C14'0.083 (4)0.071 (3)0.040 (3)0.019 (3)0.017 (3)0.014 (2)
C15'0.064 (3)0.030 (2)0.040 (2)0.007 (2)0.002 (2)0.0019 (18)
C16'0.068 (3)0.0212 (18)0.038 (2)0.0048 (19)0.006 (2)0.0026 (17)
C17'0.088 (4)0.042 (2)0.035 (3)0.009 (2)0.000 (2)0.0032 (19)
C18'0.088 (4)0.045 (2)0.034 (3)0.001 (2)0.009 (2)0.0013 (19)
C19'0.060 (3)0.048 (2)0.054 (3)0.003 (2)0.014 (2)0.011 (2)
C20'0.046 (3)0.042 (2)0.038 (2)0.0089 (19)0.0010 (19)0.0017 (18)
C21'0.051 (3)0.032 (2)0.040 (3)0.0054 (18)0.002 (2)0.0013 (17)
O50.100 (4)0.087 (3)0.077 (3)0.008 (2)0.001 (3)0.004 (2)
C220.086 (5)0.109 (5)0.097 (5)0.014 (4)0.001 (4)0.017 (4)
O1W0.102 (3)0.0531 (19)0.052 (2)0.0273 (18)0.013 (2)0.0044 (17)
Geometric parameters (Å, º) top
F1—C61.364 (4)N2'—C7'1.375 (4)
N1—C11.345 (4)N2'—C21'1.469 (5)
N1—C91.417 (4)N2'—C15'1.474 (4)
N1—C111.464 (5)N3'—C17'1.487 (5)
N2—C71.370 (4)N3'—C16'1.505 (5)
N2—C151.472 (4)N3'—H330.905 (19)
N2—C211.483 (4)N3'—H340.893 (19)
N3—C161.490 (5)O1'—C10'1.331 (5)
N3—C171.491 (5)O1'—H2'0.90 (4)
N3—H310.913 (18)O2'—C10'1.209 (5)
N3—H320.92 (4)O3'—C3'1.259 (4)
O1—C101.326 (5)O4'—C8'1.382 (4)
O1—H20.93 (6)O4'—C14'1.431 (5)
O2—C101.219 (5)C1'—C2'1.355 (5)
O3—C31.254 (4)C1'—H1'0.9300
O4—C81.377 (4)C2'—C3'1.455 (5)
O4—C141.442 (5)C2'—C10'1.474 (5)
C1—C21.350 (5)C3'—C4'1.444 (5)
C1—H10.9300C4'—C9'1.406 (5)
C2—C31.445 (5)C4'—C5'1.414 (5)
C2—C101.485 (5)C5'—C6'1.361 (5)
C3—C41.450 (5)C5'—H5'0.9300
C4—C51.403 (5)C6'—C7'1.410 (5)
C4—C91.413 (5)C7'—C8'1.411 (5)
C5—C61.342 (5)C8'—C9'1.392 (5)
C5—H50.9300C11'—C12'1.479 (6)
C6—C71.414 (5)C11'—C13'1.503 (6)
C7—C81.415 (5)C11'—H11'0.9800
C8—C91.407 (5)C12'—C13'1.489 (6)
C11—C121.472 (6)C12'—H12C0.9700
C11—C131.479 (6)C12'—H12D0.9700
C11—H110.9800C13'—H13C0.9700
C12—C131.494 (5)C13'—H13D0.9700
C12—H12A0.9700C14'—H14D0.9600
C12—H12B0.9700C14'—H14E0.9600
C13—H13A0.9700C14'—H14F0.9600
C13—H13B0.9700C15'—C16'1.506 (5)
C14—H14A0.9600C15'—H15C0.9700
C14—H14B0.9600C15'—H15D0.9700
C14—H14C0.9600C16'—C20'1.520 (5)
C15—C161.521 (5)C16'—H16'0.9800
C15—H15A0.9700C17'—C18'1.494 (6)
C15—H15B0.9700C17'—H17C0.9700
C16—C201.518 (5)C17'—H17D0.9700
C16—H16A0.9800C18'—C19'1.516 (6)
C17—C181.507 (5)C18'—H18C0.9700
C17—H17A0.9700C18'—H18D0.9700
C17—H17B0.9700C19'—C20'1.512 (5)
C18—C191.520 (5)C19'—H19C0.9700
C18—H18A0.9700C19'—H19D0.9700
C18—H18B0.9700C20'—C21'1.540 (5)
C19—C201.529 (5)C20'—H20'0.9800
C19—H19A0.9700C21'—H21C0.9700
C19—H19B0.9700C21'—H21D0.9700
C20—C211.522 (5)O5—C221.378 (6)
C20—H200.9800O5—H510.94 (2)
C21—H21A0.9700C22—H22A0.9600
C21—H21B0.9700C22—H22B0.9600
F1'—C6'1.361 (4)C22—H22C0.9600
N1'—C1'1.342 (4)O1W—H1W0.80 (4)
N1'—C9'1.408 (4)O1W—H2W0.84 (4)
N1'—C11'1.470 (5)
C1—N1—C9119.9 (3)C7'—N2'—C15'124.6 (3)
C1—N1—C11117.9 (3)C21'—N2'—C15'111.0 (3)
C9—N1—C11121.6 (3)C17'—N3'—C16'112.3 (4)
C7—N2—C15122.6 (3)C17'—N3'—H33110 (2)
C7—N2—C21125.0 (3)C16'—N3'—H33108 (2)
C15—N2—C21110.5 (3)C17'—N3'—H34107 (3)
C16—N3—C17115.6 (3)C16'—N3'—H34115 (3)
C16—N3—H31112 (2)H33—N3'—H34104 (4)
C17—N3—H31104 (2)C10'—O1'—H2'105 (3)
C16—N3—H32109 (3)C8'—O4'—C14'112.7 (3)
C17—N3—H32114 (3)N1'—C1'—C2'125.7 (3)
H31—N3—H32102 (4)N1'—C1'—H1'117.1
C10—O1—H2112 (4)C2'—C1'—H1'117.1
C8—O4—C14112.6 (3)C1'—C2'—C3'118.5 (3)
N1—C1—C2124.5 (4)C1'—C2'—C10'119.6 (4)
N1—C1—H1117.8C3'—C2'—C10'121.6 (4)
C2—C1—H1117.8O3'—C3'—C4'122.6 (3)
C1—C2—C3120.3 (3)O3'—C3'—C2'122.0 (3)
C1—C2—C10120.0 (4)C4'—C3'—C2'115.4 (3)
C3—C2—C10119.6 (4)C9'—C4'—C5'118.1 (3)
O3—C3—C2123.0 (3)C9'—C4'—C3'122.6 (3)
O3—C3—C4121.8 (3)C5'—C4'—C3'119.3 (3)
C2—C3—C4115.2 (3)C6'—C5'—C4'119.7 (3)
C5—C4—C9118.0 (3)C6'—C5'—H5'120.1
C5—C4—C3119.9 (3)C4'—C5'—H5'120.1
C9—C4—C3122.1 (3)F1'—C6'—C5'116.6 (3)
C6—C5—C4120.8 (3)F1'—C6'—C7'119.2 (3)
C6—C5—H5119.6C5'—C6'—C7'124.2 (3)
C4—C5—H5119.6N2'—C7'—C6'124.6 (3)
C5—C6—F1117.5 (3)N2'—C7'—C8'120.6 (3)
C5—C6—C7124.2 (3)C6'—C7'—C8'114.8 (3)
F1—C6—C7118.3 (3)O4'—C8'—C9'120.9 (3)
N2—C7—C6124.3 (3)O4'—C8'—C7'116.8 (3)
N2—C7—C8120.8 (3)C9'—C8'—C7'122.2 (3)
C6—C7—C8114.9 (3)C8'—C9'—C4'120.1 (3)
O4—C8—C9119.2 (3)C8'—C9'—N1'122.2 (3)
O4—C8—C7119.1 (3)C4'—C9'—N1'117.7 (3)
C9—C8—C7121.6 (3)O2'—C10'—O1'120.8 (4)
C8—C9—C4119.6 (3)O2'—C10'—C2'123.5 (4)
C8—C9—N1122.7 (3)O1'—C10'—C2'115.7 (4)
C4—C9—N1117.7 (3)N1'—C11'—C12'117.3 (4)
O2—C10—O1121.4 (4)N1'—C11'—C13'114.8 (4)
O2—C10—C2123.1 (4)C12'—C11'—C13'59.9 (3)
O1—C10—C2115.5 (4)N1'—C11'—H11'117.4
N1—C11—C12119.3 (3)C12'—C11'—H11'117.4
N1—C11—C13117.9 (3)C13'—C11'—H11'117.4
C12—C11—C1360.8 (3)C11'—C12'—C13'60.9 (3)
N1—C11—H11115.9C11'—C12'—H12C117.7
C12—C11—H11115.9C13'—C12'—H12C117.7
C13—C11—H11115.9C11'—C12'—H12D117.7
C11—C12—C1359.8 (3)C13'—C12'—H12D117.7
C11—C12—H12A117.8H12C—C12'—H12D114.8
C13—C12—H12A117.8C12'—C13'—C11'59.3 (3)
C11—C12—H12B117.8C12'—C13'—H13C117.8
C13—C12—H12B117.8C11'—C13'—H13C117.8
H12A—C12—H12B114.9C12'—C13'—H13D117.8
C11—C13—C1259.4 (3)C11'—C13'—H13D117.8
C11—C13—H13A117.8H13C—C13'—H13D115.0
C12—C13—H13A117.8O4'—C14'—H14D109.5
C11—C13—H13B117.8O4'—C14'—H14E109.5
C12—C13—H13B117.8H14D—C14'—H14E109.5
H13A—C13—H13B115.0O4'—C14'—H14F109.5
O4—C14—H14A109.5H14D—C14'—H14F109.5
O4—C14—H14B109.5H14E—C14'—H14F109.5
H14A—C14—H14B109.5N2'—C15'—C16'102.4 (3)
O4—C14—H14C109.5N2'—C15'—H15C111.3
H14A—C14—H14C109.5C16'—C15'—H15C111.3
H14B—C14—H14C109.5N2'—C15'—H15D111.3
N2—C15—C16103.1 (3)C16'—C15'—H15D111.3
N2—C15—H15A111.1H15C—C15'—H15D109.2
C16—C15—H15A111.1N3'—C16'—C15'111.8 (4)
N2—C15—H15B111.1N3'—C16'—C20'110.4 (3)
C16—C15—H15B111.1C15'—C16'—C20'104.5 (3)
H15A—C15—H15B109.1N3'—C16'—H16'110.0
N3—C16—C20113.5 (3)C15'—C16'—H16'110.0
N3—C16—C15113.3 (3)C20'—C16'—H16'110.0
C20—C16—C15103.8 (3)N3'—C17'—C18'110.7 (3)
N3—C16—H16A108.7N3'—C17'—H17C109.5
C20—C16—H16A108.7C18'—C17'—H17C109.5
C15—C16—H16A108.7N3'—C17'—H17D109.5
N3—C17—C18110.5 (3)C18'—C17'—H17D109.5
N3—C17—H17A109.6H17C—C17'—H17D108.1
C18—C17—H17A109.6C17'—C18'—C19'112.0 (4)
N3—C17—H17B109.6C17'—C18'—H18C109.2
C18—C17—H17B109.6C19'—C18'—H18C109.2
H17A—C17—H17B108.1C17'—C18'—H18D109.2
C17—C18—C19110.5 (3)C19'—C18'—H18D109.2
C17—C18—H18A109.5H18C—C18'—H18D107.9
C19—C18—H18A109.5C20'—C19'—C18'113.2 (4)
C17—C18—H18B109.5C20'—C19'—H19C108.9
C19—C18—H18B109.5C18'—C19'—H19C108.9
H18A—C18—H18B108.1C20'—C19'—H19D108.9
C18—C19—C20112.1 (4)C18'—C19'—H19D108.9
C18—C19—H19A109.2H19C—C19'—H19D107.8
C20—C19—H19A109.2C19'—C20'—C16'114.5 (3)
C18—C19—H19B109.2C19'—C20'—C21'117.1 (3)
C20—C19—H19B109.2C16'—C20'—C21'100.6 (3)
H19A—C19—H19B107.9C19'—C20'—H20'108.1
C16—C20—C21101.1 (3)C16'—C20'—H20'108.1
C16—C20—C19112.5 (3)C21'—C20'—H20'108.1
C21—C20—C19114.0 (3)N2'—C21'—C20'104.1 (3)
C16—C20—H20109.6N2'—C21'—H21C110.9
C21—C20—H20109.6C20'—C21'—H21C110.9
C19—C20—H20109.6N2'—C21'—H21D110.9
N2—C21—C20103.1 (3)C20'—C21'—H21D110.9
N2—C21—H21A111.2H21C—C21'—H21D109.0
C20—C21—H21A111.2C22—O5—H51103 (5)
N2—C21—H21B111.2O5—C22—H22A109.5
C20—C21—H21B111.2O5—C22—H22B109.5
H21A—C21—H21B109.1H22A—C22—H22B109.5
C1'—N1'—C9'119.4 (3)O5—C22—H22C109.5
C1'—N1'—C11'118.4 (3)H22A—C22—H22C109.5
C9'—N1'—C11'122.0 (3)H22B—C22—H22C109.5
C7'—N2'—C21'121.5 (3)H1W—O1W—H2W117 (6)
C9—N1—C1—C24.2 (6)C9'—N1'—C1'—C2'2.9 (6)
C11—N1—C1—C2167.4 (4)C11'—N1'—C1'—C2'171.2 (4)
N1—C1—C2—C31.8 (6)N1'—C1'—C2'—C3'4.2 (6)
N1—C1—C2—C10177.2 (4)N1'—C1'—C2'—C10'178.7 (4)
C1—C2—C3—O3176.7 (4)C1'—C2'—C3'—O3'175.6 (4)
C10—C2—C3—O31.3 (6)C10'—C2'—C3'—O3'1.2 (6)
C1—C2—C3—C44.4 (5)C1'—C2'—C3'—C4'5.6 (5)
C10—C2—C3—C4179.7 (3)C10'—C2'—C3'—C4'180.0 (3)
O3—C3—C4—C52.1 (6)O3'—C3'—C4'—C9'179.2 (4)
C2—C3—C4—C5176.8 (3)C2'—C3'—C4'—C9'0.4 (5)
O3—C3—C4—C9179.8 (4)O3'—C3'—C4'—C5'0.8 (6)
C2—C3—C4—C91.3 (5)C2'—C3'—C4'—C5'178.0 (3)
C9—C4—C5—C63.9 (6)C9'—C4'—C5'—C6'2.1 (6)
C3—C4—C5—C6178.0 (4)C3'—C4'—C5'—C6'179.4 (4)
C4—C5—C6—F1176.2 (3)C4'—C5'—C6'—F1'176.0 (3)
C4—C5—C6—C74.3 (6)C4'—C5'—C6'—C7'5.0 (6)
C15—N2—C7—C6152.9 (4)C21'—N2'—C7'—C6'141.9 (4)
C21—N2—C7—C69.7 (6)C15'—N2'—C7'—C6'17.3 (6)
C15—N2—C7—C829.5 (5)C21'—N2'—C7'—C8'39.0 (6)
C21—N2—C7—C8167.8 (3)C15'—N2'—C7'—C8'161.8 (4)
C5—C6—C7—N2179.6 (4)F1'—C6'—C7'—N2'0.4 (6)
F1—C6—C7—N20.8 (6)C5'—C6'—C7'—N2'179.4 (4)
C5—C6—C7—C82.7 (6)F1'—C6'—C7'—C8'178.7 (3)
F1—C6—C7—C8176.9 (3)C5'—C6'—C7'—C8'0.3 (6)
C14—O4—C8—C995.4 (4)C14'—O4'—C8'—C9'80.2 (4)
C14—O4—C8—C780.7 (4)C14'—O4'—C8'—C7'96.1 (4)
N2—C7—C8—O411.9 (5)N2'—C7'—C8'—O4'11.6 (5)
C6—C7—C8—O4165.9 (3)C6'—C7'—C8'—O4'167.6 (3)
N2—C7—C8—C9172.1 (3)N2'—C7'—C8'—C9'172.2 (4)
C6—C7—C8—C910.1 (5)C6'—C7'—C8'—C9'8.6 (6)
O4—C8—C9—C4165.2 (3)O4'—C8'—C9'—C4'164.4 (3)
C7—C8—C9—C410.8 (5)C7'—C8'—C9'—C4'11.7 (6)
O4—C8—C9—N113.6 (5)O4'—C8'—C9'—N1'14.3 (6)
C7—C8—C9—N1170.4 (3)C7'—C8'—C9'—N1'169.6 (4)
C5—C4—C9—C83.4 (5)C5'—C4'—C9'—C8'5.9 (6)
C3—C4—C9—C8174.6 (4)C3'—C4'—C9'—C8'172.5 (4)
C5—C4—C9—N1177.6 (3)C5'—C4'—C9'—N1'175.3 (3)
C3—C4—C9—N14.3 (5)C3'—C4'—C9'—N1'6.3 (6)
C1—N1—C9—C8171.8 (3)C1'—N1'—C9'—C8'170.8 (4)
C11—N1—C9—C816.9 (6)C11'—N1'—C9'—C8'15.3 (6)
C1—N1—C9—C47.1 (5)C1'—N1'—C9'—C4'8.0 (6)
C11—N1—C9—C4164.2 (4)C11'—N1'—C9'—C4'165.9 (4)
C1—C2—C10—O22.1 (7)C1'—C2'—C10'—O2'3.1 (7)
C3—C2—C10—O2177.5 (4)C3'—C2'—C10'—O2'177.3 (4)
C1—C2—C10—O1178.2 (4)C1'—C2'—C10'—O1'178.6 (4)
C3—C2—C10—O12.8 (6)C3'—C2'—C10'—O1'4.3 (6)
C1—N1—C11—C12113.7 (4)C1'—N1'—C11'—C12'116.0 (4)
C9—N1—C11—C1257.7 (5)C9'—N1'—C11'—C12'58.0 (5)
C1—N1—C11—C1343.3 (5)C1'—N1'—C11'—C13'48.6 (6)
C9—N1—C11—C13128.1 (4)C9'—N1'—C11'—C13'125.4 (4)
N1—C11—C12—C13107.6 (4)N1'—C11'—C12'—C13'104.3 (4)
N1—C11—C13—C12109.8 (4)N1'—C11'—C13'—C12'108.5 (4)
C7—N2—C15—C16157.3 (3)C7'—N2'—C15'—C16'175.7 (4)
C21—N2—C15—C167.6 (4)C21'—N2'—C15'—C16'14.6 (4)
C17—N3—C16—C2046.9 (4)C17'—N3'—C16'—C15'171.2 (3)
C17—N3—C16—C1571.2 (4)C17'—N3'—C16'—C20'55.4 (4)
N2—C15—C16—N3154.9 (3)N2'—C15'—C16'—N3'84.1 (4)
N2—C15—C16—C2031.3 (4)N2'—C15'—C16'—C20'35.3 (4)
C16—N3—C17—C1853.2 (4)C16'—N3'—C17'—C18'60.2 (4)
N3—C17—C18—C1957.1 (4)N3'—C17'—C18'—C19'55.9 (5)
C17—C18—C19—C2056.9 (4)C17'—C18'—C19'—C20'48.8 (5)
N3—C16—C20—C21166.2 (3)C18'—C19'—C20'—C16'45.5 (5)
C15—C16—C20—C2142.8 (4)C18'—C19'—C20'—C21'71.9 (5)
N3—C16—C20—C1944.2 (4)N3'—C16'—C20'—C19'48.0 (4)
C15—C16—C20—C1979.2 (4)C15'—C16'—C20'—C19'168.3 (3)
C18—C19—C20—C1650.0 (4)N3'—C16'—C20'—C21'78.5 (3)
C18—C19—C20—C21164.4 (3)C15'—C16'—C20'—C21'41.9 (4)
C7—N2—C21—C20176.7 (3)C7'—N2'—C21'—C20'150.5 (3)
C15—N2—C21—C2018.9 (4)C15'—N2'—C21'—C20'11.2 (4)
C16—C20—C21—N237.3 (4)C19'—C20'—C21'—N2'156.6 (4)
C19—C20—C21—N283.7 (4)C16'—C20'—C21'—N2'32.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H31···O1W0.91 (2)1.84 (2)2.736 (5)167 (3)
N3—H32···Cl10.92 (4)2.23 (2)3.149 (4)174 (4)
O1—H2···O30.93 (6)1.64 (6)2.487 (4)150 (5)
N3—H33···Cl10.91 (2)2.20 (2)3.059 (4)159 (3)
N3—H34···Cl1i0.89 (2)2.48 (3)3.263 (4)147 (3)
O1—H2···O30.90 (4)1.68 (4)2.541 (4)159 (4)
O5—H51···Cl10.94 (2)2.27 (2)3.210 (5)174 (7)
O1W—H1W···O2ii0.80 (4)1.99 (2)2.790 (5)169 (5)
O1W—H2W···Cl1ii0.84 (4)2.30 (2)3.126 (4)171 (6)
Symmetry codes: (i) x1, y, z1; (ii) x+2, y1/2, z+1.

Experimental details

Crystal data
Chemical formulaC21H25FN3O4+·Cl·0.5H2O·0.5CH4O
Mr462.92
Crystal system, space groupMonoclinic, P21
Temperature (K)273
a, b, c (Å)6.828 (2), 20.929 (6), 15.357 (5)
β (°) 92.007 (5)
V3)2193.4 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.21 × 0.19 × 0.09
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
19500, 7616, 5008
Rint0.076
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.104, 0.90
No. of reflections7616
No. of parameters607
No. of restraints8
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.26, 0.24
Absolute structureFlack & Bernardinelli (2000), 3643 Friedel pairs
Absolute structure parameter0.12 (6)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Sheldrick, 1990) and Mercury (Macrae et al., 2006), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H31···O1W0.913 (18)1.84 (2)2.736 (5)167 (3)
N3—H32···Cl10.92 (4)2.23 (2)3.149 (4)174 (4)
O1—H2···O30.93 (6)1.64 (6)2.487 (4)150 (5)
N3'—H33···Cl1'0.905 (19)2.20 (2)3.059 (4)159 (3)
N3'—H34···Cl1i0.893 (19)2.48 (3)3.263 (4)147 (3)
O1'—H2'···O3'0.90 (4)1.68 (4)2.541 (4)159 (4)
O5—H51···Cl1'0.94 (2)2.27 (2)3.210 (5)174 (7)
O1W—H1W···O2ii0.80 (4)1.99 (2)2.790 (5)169 (5)
O1W—H2W···Cl1'ii0.84 (4)2.30 (2)3.126 (4)171 (6)
Symmetry codes: (i) x1, y, z1; (ii) x+2, y1/2, z+1.
 

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