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Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): o714–o715.
Published online 2010 February 27. doi:  10.1107/S1600536810006835
PMCID: PMC2983575

4-(3-Carb­oxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-7-quinol­yl)-1-methyl­piper­azin­ium picrate

Abstract

The pefloxacinium cation of the title salt, C17H21FN3O3 +·C6H2N3O7 , is composed of an essentially planar quinoline ring system [maximum deviation = 0.021 (2) Å] and a piperazine ring, which adopts a chair conformation. In the picrate anion, the two O atoms of one of the o-NO2 groups are disordered over two positions, with an occupancy ratio of 0.56 (4):0.44 (4). In the crystal structure, cations and anions are connected by inter­molecular N—H(...)O, O—H(...)O, C—H(...)O and C—H(...)F hydrogen bonds, forming a three-dimensional network. In addition, π–π inter­actions between the pyridine rings and between the benzene rings of the anions, with centroid–centroid distances of 3.6103 (12) and 3.5298 (11) Å, respectively, are observed.

Related literature

For background to the biological activity, pharmacokinetic properties and therapeutic use of pefloxacin, a synthetic chemotherapeutic agent used to treat severe bacterial infections, see: Mizuki et al. (1996 [triangle]); Gonzalez & Henwood (1989 [triangle]); Tripathi (1995 [triangle]); Ross & Riley (1990 [triangle]); Burkhardt et al. (1997 [triangle]). For the silver(I), manganese(II) and cobalt(II) derivatives of the pefloxacin anion, see: Baenziger et al. (1986 [triangle]); An, Huang & Qi (2007 [triangle]); An, Qi & Huang (2007 [triangle]). For related structures, see; An & Liang (2008 [triangle]); Florence et al. (2000 [triangle]); Hu & Yu (2005 [triangle]); Parvez et al. (2000 [triangle]). For hydrogen-bonding motifs see: Bernstein et al. (1995 [triangle]). For ring conformations, see: Cremer & Pople (1975 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o714-scheme1.jpg

Experimental

Crystal data

  • C17H21FN3O3 +·C6H2N3O7
  • M r = 562.47
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o714-efi1.jpg
  • a = 7.2645 (1) Å
  • b = 9.1987 (2) Å
  • c = 20.2253 (4) Å
  • α = 77.116 (1)°
  • β = 81.315 (1)°
  • γ = 67.124 (1)°
  • V = 1210.77 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.13 mm−1
  • T = 296 K
  • 0.36 × 0.13 × 0.13 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.955, T max = 0.984
  • 23708 measured reflections
  • 5523 independent reflections
  • 3682 reflections with I > 2s(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.123
  • S = 1.03
  • 5523 reflections
  • 472 parameters
  • All H-atom parameters refined
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810006835/tk2633sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006835/tk2633Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. MH thanks Universiti Sains Malaysia for a post-doctoral research fellowship. DNS thanks Mangalore University for research facilities.

supplementary crystallographic information

Comment

Pefloxacin is a synthetic chemotherapeutic agent used to treat severe and life-threatening bacterial infections (Mizuki et al., 1996). A review of its anti-bacterial activity, pharmacokinetic properties and therapeutic use is available (Gonzalez & Henwood, 1989). Pefloxacin is commonly referred to as a fluoroquinolone (or quinolone) drug and is a member of the fluoroquinolone class of anti-bacterials. It is an analog of norfloxacin and is a synthetic fluoroquinolone, belonging to the third generation of quinolones. As an antibacterial drug, it is highly effective against both Gram-negative and Gram-positive pathogens that are resistant to other anti-bacterials (Tripathi, 1995; Ross et al., 1990). Pefloxacin is well known to be associated with high incidence of arthropathy in humans because the drug affects articular cartilage and the epiphyseal growth plate (Burkhardt et al., 1997). The silver(I), manganese(II) and cobalt(II) derivatives of the pefloxacin anion have been reported (Baenziger et al., 1986; An, Huang, & Qi, 2007; An, Qi & Huang, 2007). The crystal structures of silver pefloxacin (Baenziger et al., 1986), pefloxacinium methane sulfonate 0.10-hydrate (Parvez et al., 2000), norfloxacin dihydrate (Florence et al., 2000), norfloxacin picrate (Hu & Yu, 2005), 1-ethyl-6-fluoro-7-(4-methylpiperazin-4-ium-1-yl) -4-oxo-1,4-dihydroquinoline-3-carboxylate hexahydrate (An & Liang, 2008) have been reported. In view of the importance of pefloxacin, this paper reports the crystal structure of the title compound.

The asymmetric unit of the title compound (Fig. 1), contains a protonated pefloxacinium cation and a picrate anion. The cation is composed of an essentially planar quinoline ring system [maximum deviation 0.021 (2) Å]. The six-membered piperazinyl ring adopts a chair conformation with puckering parameters (Cremer & Pople, 1975) Q = 0.5621 (2) Å , Θ = 174.05 (18)° and [var phi] = 169 (2)°. In the picrate anion, atoms O2 and O3 are disordered over two positions, with occupancy ratio of 0.56 (4):0.44 (4). The phenolate oxygen atoms are bent slightly away from the mean plane of the benzene ring (torsion angle O1—C2—C3—C4 = -177.76 (18)°).

In the crystal structure (Fig. 2), the picrate anion interacts with the cations through bifurcated N6—H1N6···O1 and N6—H1N6···O7 hydrogen bonds, forming an R12(6) (Bernstein et al., 1995) ring motif. There is an intramolecular O9—H1O9···O10 hydrogen bond between the carbonyl and carboxyl groups in the cation, which generates an S(6) ring motif. The crystal structure is further stabilized by several weak C—H···O and C—H···F interactions (Table 1), forming a three-dimensional network. Also, π–π interactions between pyridine rings, and between benzene rings of anions/anions, with centroid-to-centroid distances = 3.6103 (12) Å and 3.5298 (11) Å, respectively, are observed.

Experimental

Each of the pefloxacin (3.33 g, 0.01 mol) and picric acid (2.29 g, 0.01 mol) were individually dissolved in water (60 ml). The solutions were mixed and 5 M HCl (2 ml) was added with stirring for a few minutes. The product formed was filtered and dried. Yellow crystals of pefloxacinium picrate were obtained by slow evaporation in DMF (m.p.: 515 K).

Refinement

All the H atoms were located in a difference Fourier map and allowed to refine freely [N–H = 0.905 (19) Å, O—H = 0.96 (3) Å, C–H = 0.88 (19)–1.01 (3) Å]. In the picrate anion, atoms O2 and O3 are disordered over two positions, with an occupancy ratio of 0.56 (4):0.44 (4).

Figures

Fig. 1.
The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
Fig. 2.
The crystal packing of the title compound, showing hydrogen-bonded (dashed lines) network.

Crystal data

C17H21FN3O3+·C6H2N3O7Z = 2
Mr = 562.47F(000) = 584
Triclinic, P1Dx = 1.543 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.2645 (1) ÅCell parameters from 4949 reflections
b = 9.1987 (2) Åθ = 2.5–31.8°
c = 20.2253 (4) ŵ = 0.13 mm1
α = 77.116 (1)°T = 296 K
β = 81.315 (1)°Block, yellow
γ = 67.124 (1)°0.36 × 0.13 × 0.13 mm
V = 1210.77 (4) Å3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer5523 independent reflections
Radiation source: fine-focus sealed tube3682 reflections with I > 2s(I)
graphiteRint = 0.039
[var phi] and ω scansθmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −9→9
Tmin = 0.955, Tmax = 0.984k = −11→11
23708 measured reflectionsl = −26→26

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123All H-atom parameters refined
S = 1.03w = 1/[σ2(Fo2) + (0.0539P)2 + 0.1877P] where P = (Fo2 + 2Fc2)/3
5523 reflections(Δ/σ)max = 0.001
472 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = −0.21 e Å3

Special details

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.
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 > 2sigma(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)

xyzUiso*/UeqOcc. (<1)
O10.4979 (2)0.79508 (17)0.88294 (6)0.0614 (4)
O20.7151 (13)0.5178 (13)0.8445 (5)0.067 (2)0.56 (4)
O30.9703 (16)0.3754 (18)0.9011 (8)0.075 (3)0.56 (4)
O2B0.768 (5)0.546 (3)0.8376 (7)0.120 (6)0.44 (4)
O3B0.934 (4)0.357 (3)0.9074 (10)0.103 (5)0.44 (4)
O40.8735 (3)0.32881 (19)1.14260 (8)0.0788 (5)
O50.6553 (3)0.5215 (2)1.18879 (7)0.0730 (5)
O60.2844 (2)1.00907 (18)1.04797 (8)0.0663 (4)
O70.2049 (3)0.9961 (2)0.95255 (9)0.0994 (7)
N10.8047 (2)0.4832 (2)0.89513 (8)0.0473 (4)
N20.7383 (3)0.4603 (2)1.13878 (9)0.0543 (4)
N30.3077 (3)0.9389 (2)1.00085 (9)0.0531 (4)
C10.7049 (2)0.5634 (2)0.95257 (8)0.0367 (4)
C20.5487 (2)0.7206 (2)0.94034 (8)0.0388 (4)
C30.4645 (3)0.7803 (2)1.00324 (9)0.0391 (4)
C40.5270 (3)0.6985 (2)1.06618 (10)0.0422 (4)
C50.6760 (3)0.5484 (2)1.07199 (9)0.0425 (4)
C60.7669 (3)0.4806 (2)1.01542 (9)0.0404 (4)
F10.63677 (18)−0.03326 (12)0.57808 (5)0.0561 (3)
O8−0.0325 (3)0.9171 (2)0.40639 (8)0.0782 (5)
O90.0924 (3)0.7207 (2)0.34701 (8)0.0711 (5)
O100.2917 (2)0.43985 (18)0.40332 (7)0.0611 (4)
N40.2108 (2)0.60713 (17)0.58140 (7)0.0395 (3)
N50.5335 (2)0.06173 (16)0.70402 (7)0.0355 (3)
N60.2153 (2)0.01715 (17)0.80261 (7)0.0381 (3)
C70.1335 (3)0.7054 (2)0.52424 (10)0.0452 (5)
C80.1526 (3)0.6553 (2)0.46406 (9)0.0456 (5)
C90.2625 (3)0.4915 (2)0.45840 (9)0.0440 (5)
C100.3409 (3)0.3855 (2)0.52080 (8)0.0375 (4)
C110.4521 (3)0.2212 (2)0.52173 (9)0.0419 (4)
C120.5179 (3)0.1222 (2)0.58059 (9)0.0386 (4)
C130.4736 (2)0.1723 (2)0.64432 (8)0.0329 (4)
C140.3771 (2)0.3363 (2)0.64216 (9)0.0341 (4)
C150.3112 (2)0.4432 (2)0.58177 (8)0.0343 (4)
C160.4921 (3)−0.0875 (2)0.71661 (10)0.0403 (4)
C170.2763 (3)−0.0593 (2)0.74081 (9)0.0403 (4)
C180.2690 (3)0.1625 (2)0.79291 (10)0.0409 (4)
C190.4868 (3)0.1236 (2)0.76759 (9)0.0386 (4)
C20−0.0031 (3)0.0581 (3)0.82167 (14)0.0571 (6)
C210.1823 (3)0.6765 (3)0.64328 (11)0.0493 (5)
C220.0028 (4)0.6633 (4)0.68827 (13)0.0664 (7)
C230.0618 (3)0.7773 (3)0.40435 (11)0.0563 (6)
H40.468 (3)0.743 (2)1.1031 (11)0.055 (6)*
H60.864 (3)0.386 (2)1.0177 (9)0.046 (5)*
H70.066 (3)0.813 (3)0.5297 (10)0.055 (6)*
H110.485 (3)0.181 (2)0.4813 (10)0.047 (5)*
H140.349 (2)0.379 (2)0.6821 (9)0.036 (5)*
H16A0.526 (3)−0.136 (2)0.6761 (11)0.057 (6)*
H16B0.583 (3)−0.163 (2)0.7505 (10)0.053 (5)*
H17A0.193 (3)0.012 (2)0.7078 (9)0.044 (5)*
H17B0.251 (3)−0.164 (3)0.7550 (10)0.059 (6)*
H18A0.245 (3)0.196 (2)0.8351 (10)0.043 (5)*
H18B0.182 (3)0.241 (2)0.7603 (10)0.045 (5)*
H19A0.569 (3)0.039 (2)0.8001 (9)0.040 (5)*
H19B0.521 (2)0.220 (2)0.7621 (9)0.040 (5)*
H20A−0.038 (3)0.107 (3)0.8617 (12)0.072 (7)*
H20B−0.079 (4)0.131 (3)0.7848 (13)0.081 (8)*
H20C−0.033 (3)−0.043 (3)0.8318 (12)0.080 (8)*
H21A0.303 (3)0.623 (2)0.6670 (9)0.046 (5)*
H21B0.161 (3)0.781 (3)0.6285 (10)0.055 (6)*
H22A−0.106 (4)0.710 (3)0.6634 (14)0.096 (9)*
H22B0.022 (4)0.552 (4)0.7065 (13)0.092 (9)*
H22C−0.013 (4)0.715 (3)0.7274 (15)0.103 (9)*
H1O90.179 (4)0.610 (4)0.3556 (15)0.110 (11)*
H1N60.284 (3)−0.055 (2)0.8372 (10)0.044 (5)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0640 (9)0.0613 (9)0.0329 (7)−0.0004 (7)−0.0099 (6)0.0052 (6)
O20.075 (3)0.091 (4)0.032 (3)−0.022 (3)−0.008 (2)−0.019 (3)
O30.046 (3)0.075 (4)0.094 (7)−0.001 (3)−0.005 (3)−0.037 (4)
O2B0.146 (11)0.093 (7)0.041 (3)0.026 (7)0.016 (6)0.001 (4)
O3B0.114 (10)0.072 (7)0.058 (5)0.034 (7)0.006 (7)−0.015 (4)
O40.1096 (14)0.0488 (10)0.0600 (10)−0.0117 (9)−0.0349 (9)0.0128 (8)
O50.1082 (13)0.0755 (11)0.0342 (8)−0.0327 (10)−0.0172 (8)−0.0017 (8)
O60.0818 (10)0.0514 (9)0.0601 (10)−0.0210 (8)0.0176 (8)−0.0208 (8)
O70.0998 (13)0.0821 (13)0.0596 (11)0.0313 (10)−0.0219 (10)−0.0093 (9)
N10.0471 (9)0.0478 (11)0.0434 (10)−0.0148 (8)0.0000 (8)−0.0083 (8)
N20.0789 (12)0.0483 (11)0.0388 (10)−0.0286 (9)−0.0205 (9)0.0067 (8)
N30.0613 (10)0.0434 (10)0.0418 (10)−0.0125 (8)0.0051 (8)−0.0009 (8)
C10.0402 (9)0.0377 (10)0.0325 (9)−0.0152 (7)−0.0031 (7)−0.0047 (8)
C20.0416 (9)0.0395 (10)0.0310 (9)−0.0138 (8)−0.0066 (7)0.0024 (8)
C30.0439 (9)0.0336 (10)0.0362 (10)−0.0135 (7)−0.0027 (7)−0.0010 (8)
C40.0556 (11)0.0425 (11)0.0330 (10)−0.0240 (9)−0.0026 (8)−0.0049 (8)
C50.0565 (11)0.0398 (11)0.0333 (10)−0.0226 (9)−0.0138 (8)0.0050 (8)
C60.0438 (10)0.0316 (10)0.0443 (11)−0.0131 (8)−0.0118 (8)0.0006 (8)
F10.0842 (8)0.0348 (6)0.0393 (6)−0.0115 (5)−0.0012 (5)−0.0083 (5)
O80.0905 (12)0.0572 (11)0.0693 (11)−0.0164 (9)−0.0349 (9)0.0226 (8)
O90.0922 (12)0.0720 (12)0.0470 (9)−0.0327 (10)−0.0345 (8)0.0176 (8)
O100.0940 (11)0.0621 (10)0.0345 (8)−0.0367 (8)−0.0223 (7)0.0031 (7)
N40.0437 (8)0.0334 (8)0.0361 (8)−0.0114 (6)−0.0087 (6)0.0029 (6)
N50.0403 (7)0.0311 (8)0.0285 (7)−0.0093 (6)−0.0023 (6)0.0002 (6)
N60.0377 (7)0.0351 (8)0.0320 (8)−0.0092 (6)−0.0041 (6)0.0057 (7)
C70.0468 (10)0.0387 (11)0.0453 (11)−0.0154 (9)−0.0107 (8)0.0066 (9)
C80.0454 (10)0.0489 (12)0.0415 (11)−0.0233 (9)−0.0161 (8)0.0133 (9)
C90.0529 (11)0.0516 (12)0.0352 (10)−0.0310 (9)−0.0149 (8)0.0066 (9)
C100.0455 (9)0.0406 (10)0.0299 (9)−0.0230 (8)−0.0085 (7)0.0038 (7)
C110.0595 (11)0.0435 (11)0.0293 (9)−0.0265 (9)−0.0054 (8)−0.0045 (8)
C120.0490 (10)0.0306 (10)0.0352 (10)−0.0154 (8)−0.0019 (8)−0.0033 (7)
C130.0350 (8)0.0342 (9)0.0281 (9)−0.0141 (7)−0.0029 (7)0.0002 (7)
C140.0387 (9)0.0334 (10)0.0287 (9)−0.0129 (7)−0.0033 (7)−0.0030 (7)
C150.0360 (8)0.0324 (9)0.0332 (9)−0.0144 (7)−0.0063 (7)0.0025 (7)
C160.0508 (10)0.0286 (10)0.0322 (10)−0.0089 (8)−0.0008 (8)0.0012 (8)
C170.0506 (10)0.0344 (10)0.0328 (10)−0.0154 (8)−0.0088 (8)0.0035 (8)
C180.0506 (10)0.0355 (10)0.0314 (10)−0.0132 (8)0.0014 (8)−0.0033 (8)
C190.0456 (10)0.0404 (11)0.0277 (9)−0.0156 (8)−0.0083 (7)0.0013 (8)
C200.0404 (10)0.0558 (14)0.0611 (15)−0.0133 (10)0.0024 (10)0.0048 (12)
C210.0618 (13)0.0315 (11)0.0475 (12)−0.0074 (9)−0.0142 (10)−0.0037 (9)
C220.0521 (13)0.080 (2)0.0512 (14)−0.0029 (12)−0.0062 (11)−0.0177 (14)
C230.0603 (12)0.0582 (14)0.0483 (13)−0.0283 (11)−0.0245 (10)0.0201 (11)

Geometric parameters (Å, °)

O1—C21.2375 (19)N6—H1N60.905 (19)
O2—N11.212 (8)C7—C81.365 (3)
O3—N11.228 (13)C7—H70.94 (2)
O2B—N11.196 (13)C8—C91.426 (3)
O3B—N11.177 (17)C8—C231.488 (3)
O4—N21.221 (2)C9—C101.451 (2)
O5—N21.229 (2)C10—C151.404 (2)
O6—N31.222 (2)C10—C111.407 (3)
O7—N31.214 (2)C11—C121.351 (2)
N1—C11.460 (2)C11—H110.932 (19)
N2—C51.448 (2)C12—C131.415 (2)
N3—C31.457 (2)C13—C141.388 (2)
C1—C61.368 (2)C14—C151.401 (2)
C1—C21.446 (2)C14—H140.936 (17)
C2—C31.452 (2)C16—C171.508 (3)
C3—C41.369 (2)C16—H16A0.97 (2)
C4—C51.377 (3)C16—H16B0.98 (2)
C4—H40.90 (2)C17—H17A0.929 (19)
C5—C61.380 (3)C17—H17B1.02 (2)
C6—H60.882 (19)C18—C191.514 (3)
F1—C121.3609 (19)C18—H18A0.942 (19)
O8—C231.206 (3)C18—H18B0.956 (19)
O9—C231.329 (3)C19—H19A0.959 (18)
O9—H1O90.96 (3)C19—H19B0.994 (18)
O10—C91.264 (2)C20—H20A0.97 (2)
N4—C71.343 (2)C20—H20B0.96 (3)
N4—C151.396 (2)C20—H20C1.01 (3)
N4—C211.480 (2)C21—C221.502 (3)
N5—C131.396 (2)C21—H21A0.964 (19)
N5—C191.462 (2)C21—H21B0.90 (2)
N5—C161.477 (2)C22—H22A0.91 (3)
N6—C201.491 (2)C22—H22B0.97 (3)
N6—C171.496 (2)C22—H22C0.98 (3)
N6—C181.498 (2)
O3B—N1—O2B120.7 (12)C12—C11—H11119.8 (12)
O3B—N1—O2119.9 (11)C10—C11—H11119.8 (12)
O2B—N1—O225.4 (19)C11—C12—F1118.09 (16)
O3B—N1—O317.2 (18)C11—C12—C13123.53 (16)
O2B—N1—O3114.2 (11)F1—C12—C13118.36 (14)
O2—N1—O3121.9 (8)C14—C13—N5123.69 (15)
O3B—N1—C1116.8 (10)C14—C13—C12115.50 (15)
O2B—N1—C1122.4 (7)N5—C13—C12120.75 (15)
O2—N1—C1118.6 (5)C13—C14—C15122.18 (16)
O3—N1—C1119.3 (7)C13—C14—H14120.3 (11)
O4—N2—O5122.98 (17)C15—C14—H14117.5 (11)
O4—N2—C5118.14 (18)N4—C15—C14120.91 (15)
O5—N2—C5118.87 (17)N4—C15—C10118.98 (14)
O7—N3—O6122.52 (18)C14—C15—C10120.08 (16)
O7—N3—C3119.07 (17)N5—C16—C17111.86 (15)
O6—N3—C3118.41 (17)N5—C16—H16A111.3 (12)
C6—C1—C2124.48 (16)C17—C16—H16A109.6 (12)
C6—C1—N1116.28 (16)N5—C16—H16B106.4 (11)
C2—C1—N1119.24 (15)C17—C16—H16B111.3 (11)
O1—C2—C1123.51 (16)H16A—C16—H16B106.2 (16)
O1—C2—C3124.90 (16)N6—C17—C16111.76 (15)
C1—C2—C3111.58 (14)N6—C17—H17A105.8 (11)
C4—C3—C2124.16 (16)C16—C17—H17A110.2 (11)
C4—C3—N3116.38 (16)N6—C17—H17B105.1 (11)
C2—C3—N3119.44 (15)C16—C17—H17B112.0 (11)
C3—C4—C5119.36 (18)H17A—C17—H17B111.7 (16)
C3—C4—H4119.3 (13)N6—C18—C19110.49 (15)
C5—C4—H4121.4 (13)N6—C18—H18A107.9 (11)
C4—C5—C6121.23 (16)C19—C18—H18A110.3 (11)
C4—C5—N2119.28 (18)N6—C18—H18B105.3 (11)
C6—C5—N2119.49 (17)C19—C18—H18B111.5 (11)
C1—C6—C5119.18 (17)H18A—C18—H18B111.3 (16)
C1—C6—H6117.8 (12)N5—C19—C18112.19 (14)
C5—C6—H6123.0 (12)N5—C19—H19A105.6 (10)
C23—O9—H1O9108.0 (18)C18—C19—H19A108.9 (10)
C7—N4—C15119.85 (16)N5—C19—H19B110.7 (10)
C7—N4—C21118.47 (16)C18—C19—H19B109.8 (10)
C15—N4—C21121.66 (14)H19A—C19—H19B109.6 (14)
C13—N5—C19117.44 (14)N6—C20—H20A108.9 (14)
C13—N5—C16118.83 (14)N6—C20—H20B109.9 (14)
C19—N5—C16108.08 (14)H20A—C20—H20B110 (2)
C20—N6—C17110.80 (17)N6—C20—H20C109.0 (14)
C20—N6—C18110.72 (16)H20A—C20—H20C110 (2)
C17—N6—C18111.68 (14)H20B—C20—H20C109.3 (19)
C20—N6—H1N6108.7 (11)N4—C21—C22112.15 (19)
C17—N6—H1N6107.7 (11)N4—C21—H21A108.2 (11)
C18—N6—H1N6107.1 (12)C22—C21—H21A111.4 (11)
N4—C7—C8123.61 (19)N4—C21—H21B105.7 (13)
N4—C7—H7113.1 (12)C22—C21—H21B108.4 (13)
C8—C7—H7123.3 (12)H21A—C21—H21B110.9 (17)
C7—C8—C9120.63 (16)C21—C22—H22A108.4 (17)
C7—C8—C23118.05 (19)C21—C22—H22B110.9 (15)
C9—C8—C23121.28 (19)H22A—C22—H22B110 (2)
O10—C9—C8123.29 (16)C21—C22—H22C109.2 (17)
O10—C9—C10121.36 (18)H22A—C22—H22C112 (2)
C8—C9—C10115.36 (17)H22B—C22—H22C107 (2)
C15—C10—C11117.85 (15)O8—C23—O9121.43 (19)
C15—C10—C9121.42 (17)O8—C23—C8123.9 (2)
C11—C10—C9120.73 (16)O9—C23—C8114.6 (2)
C12—C11—C10120.33 (17)
O3B—N1—C1—C6−2.1 (18)O10—C9—C10—C11−0.1 (3)
O2B—N1—C1—C6−177 (2)C8—C9—C10—C11−179.94 (16)
O2—N1—C1—C6153.5 (6)C15—C10—C11—C123.5 (3)
O3—N1—C1—C6−21.4 (8)C9—C10—C11—C12−177.41 (16)
O3B—N1—C1—C2178.6 (18)C10—C11—C12—F1−175.41 (15)
O2B—N1—C1—C23(2)C10—C11—C12—C133.1 (3)
O2—N1—C1—C2−25.9 (6)C19—N5—C13—C141.4 (2)
O3—N1—C1—C2159.2 (7)C16—N5—C13—C14134.68 (17)
C6—C1—C2—O1178.26 (18)C19—N5—C13—C12178.36 (15)
N1—C1—C2—O1−2.5 (3)C16—N5—C13—C12−48.4 (2)
C6—C1—C2—C3−0.2 (2)C11—C12—C13—C14−7.6 (2)
N1—C1—C2—C3179.05 (15)F1—C12—C13—C14170.87 (14)
O1—C2—C3—C4−177.76 (18)C11—C12—C13—N5175.20 (16)
C1—C2—C3—C40.7 (2)F1—C12—C13—N5−6.3 (2)
O1—C2—C3—N30.3 (3)N5—C13—C14—C15−177.14 (15)
C1—C2—C3—N3178.69 (15)C12—C13—C14—C155.8 (2)
O7—N3—C3—C4−157.8 (2)C7—N4—C15—C14−174.14 (15)
O6—N3—C3—C421.9 (2)C21—N4—C15—C144.4 (2)
O7—N3—C3—C224.0 (3)C7—N4—C15—C104.2 (2)
O6—N3—C3—C2−156.28 (17)C21—N4—C15—C10−177.34 (16)
C2—C3—C4—C5−1.4 (3)C13—C14—C15—N4178.65 (15)
N3—C3—C4—C5−179.47 (16)C13—C14—C15—C100.4 (2)
C3—C4—C5—C61.6 (3)C11—C10—C15—N4176.55 (15)
C3—C4—C5—N2−178.45 (16)C9—C10—C15—N4−2.6 (2)
O4—N2—C5—C4−178.56 (18)C11—C10—C15—C14−5.1 (2)
O5—N2—C5—C40.5 (3)C9—C10—C15—C14175.75 (15)
O4—N2—C5—C61.4 (3)C13—N5—C16—C17−77.71 (19)
O5—N2—C5—C6−179.54 (17)C19—N5—C16—C1759.43 (18)
C2—C1—C6—C50.5 (3)C20—N6—C17—C16174.57 (16)
N1—C1—C6—C5−178.80 (15)C18—N6—C17—C1650.64 (19)
C4—C5—C6—C1−1.2 (3)N5—C16—C17—N6−55.40 (19)
N2—C5—C6—C1178.90 (16)C20—N6—C18—C19−175.03 (17)
C15—N4—C7—C8−2.3 (3)C17—N6—C18—C19−51.05 (19)
C21—N4—C7—C8179.16 (17)C13—N5—C19—C1877.00 (19)
N4—C7—C8—C9−1.3 (3)C16—N5—C19—C18−60.83 (18)
N4—C7—C8—C23−179.19 (17)N6—C18—C19—N557.51 (19)
C7—C8—C9—O10−177.07 (17)C7—N4—C21—C2294.7 (2)
C23—C8—C9—O100.7 (3)C15—N4—C21—C22−83.8 (2)
C7—C8—C9—C102.8 (2)C7—C8—C23—O8−2.2 (3)
C23—C8—C9—C10−179.41 (16)C9—C8—C23—O8179.97 (19)
O10—C9—C10—C15179.02 (15)C7—C8—C23—O9177.75 (17)
C8—C9—C10—C15−0.8 (2)C9—C8—C23—O9−0.1 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O9—H1O9···O100.96 (3)1.62 (3)2.519 (2)155 (3)
N6—H1N6···O1i0.91 (2)1.84 (2)2.701 (2)159 (2)
N6—H1N6···O7i0.91 (2)2.422 (19)2.987 (2)120.6 (15)
C6—H6···O30.878 (19)2.38 (2)2.706 (16)102.3 (14)
C11—H11···F1ii0.933 (19)2.46 (2)3.209 (2)137.3 (18)
C16—H16A···F10.97 (2)2.18 (2)2.846 (2)124.6 (15)
C17—H17A···O8iii0.928 (19)2.582 (19)3.430 (3)152.2 (14)
C17—H17B···O4iv1.02 (2)2.55 (2)3.407 (3)141.2 (16)
C18—H18A···O3v0.940 (19)2.47 (2)3.241 (16)139.2 (18)
C19—H19B···O5vi0.990 (17)2.566 (17)3.300 (2)131.0 (13)
C20—H20A···O7i0.97 (2)2.51 (2)3.079 (3)118.0 (18)
C20—H20C···O4iv1.01 (3)2.39 (3)3.245 (3)141.8 (19)
C21—H21B···O8vii0.90 (3)2.53 (3)3.415 (3)169 (2)

Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y, −z+1; (iii) −x, −y+1, −z+1; (iv) −x+1, −y, −z+2; (v) x−1, y, z; (vi) −x+1, −y+1, −z+2; (vii) −x, −y+2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2633).

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