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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): o2173.
Published online 2009 August 15. doi:  10.1107/S1600536809032188
PMCID: PMC2970016

5-Amino-1-phenyl-3-trifluoro­methyl-1H-pyrazole-4-carboxylic acid

Abstract

In the title compound, C11H8F3N3O2, there are two mol­ecules in the asymmetric unit wherein the phenyl rings make dihedral angles of 65.3 (2) and 85.6 (2)° with the pyrazole rings. In the crystal, pairs of mol­ecules are held together by O—H(...)O hydrogen bonds between the carboxyl groups, forming a centrosymmetric dimer with an R 2 2(8) motif. Intra­molecular N—H(...)O inter­actions are also present.

Related literature

For general background, see: Caruso & Rossi (2004 [triangle]); Maggio et al., (2008 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]).

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Object name is e-65-o2173-scheme1.jpg

Experimental

Crystal data

  • C11H8F3N3O2
  • M r = 271.20
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2173-efi1.jpg
  • a = 9.757 (3) Å
  • b = 10.740 (3) Å
  • c = 21.277 (6) Å
  • β = 93.716 (3)°
  • V = 2225 (1) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.15 mm−1
  • T = 125 K
  • 0.30 × 0.18 × 0.05 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1997 [triangle]) T min = 0.957, T max = 0.993
  • 20692 measured reflections
  • 3772 independent reflections
  • 2737 reflections with I > 2σ(I)
  • R int = 0.072

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.140
  • S = 1.01
  • 3772 reflections
  • 368 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.43 e Å−3
  • Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809032188/bx2218sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032188/bx2218Isup2.hkl

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

Acknowledgments

We acknowkledge US NSF grant No. 0521237 for the X-ray diffractometer.

supplementary crystallographic information

Comment

We report here the structure of the title compound (I), isolated during attempts to synthesize Ti(C5H5)2(C11H7F3N3O2)2. In the title compound C11H8F3N3O2, there are two molecules in the asymmetric unit that differ in the dihedral angle formed between the phenyl and pyrazole rings, 65.3 (2) and 85.6 (2)°. The pairs of molecules are held together by O—H···O hydrogen bonds between the carboxyl groups, forming a centrosymmetric dimer with an R22 (8) motif, Fig. 2. (Bernstein et al., 1995) . Related compounds of this ligand show antiproliferative and apoptotic effects against K562, K562-R (imatinib mesilate resistant), HL60 and multidrug resistant HL60 cell lines (Maggio et al., 2008).

Experimental

The synthesis of title compound has been described by Maggio et al., 2008. The title compound was reacted with titanocene dichloride, (C5H5)2TiCl2. Elemental analysis {C, 53.50, H, 3.37, N, 11.70%. Found: C, 53.66, H, 3.45, N, 11.54%} indicated formation of Cp2Ti(ligand)2,= Ti(C5H5)2(C11H7F3N3O2)2, ligand = 5-amino-1-phenyl-3- (trifluoromethyl)-1H-pyrazole-4-carboxylate. Melting point 190–195°C. IR(nujol, cm-1): 3439w, 3332w (N—H), 3049w (Carom-H), 1661 s, 1611 s (COO), 1537 s, 1486 s (C=N + C=C). 1H NMR (CDCl3): 5.59br (10H, Ti—C5H5), 6.40br, 6.60br (6H, –NH2), 7.55 mbr (10H, Carom-H). Good solubility in chloroform, methanol, dimethylsulfoxide; lower solubilty in acetonitrile; insoluble in water. Upon recrystallization flat needles were obtained, they were studied to determine its crystal and molecular structure and revealed only the ligand. Ligand cleavage is a non unusual feature for Ti complexes that show a marked tendency to evolve towards titanium dioxide (Caruso & Rossi, 2004). The title compound synthesis has been described (Maggio et al.). Related compounds of this ligand show antiproliferative and apoptotic effects against K562, K562—R (imatinib mesilate resistant), HL60 and multidrug resistant HL60 cell lines (Maggio et al., 2008).

Refinement

H atoms bonded to C atoms were located from difference maps and treated as riding model, with C—H distance of 0.95 Å and with Uiso(H) = 1.2Ueq(C). O and N-bound H atoms were freely refined, giving distances and Uiso in the ranges O-H = [ 0.91 (4)-0.94 (4) ]Å, N-H = [0.85 (4)-0.95 (4)] Å and Uiso(H) = [0.067 (12)-0.076 (14)] Å2 Ueq(O) and Uiso(H) = [0.041 (9)-0.066 (12)] Å2 Ueq(N).

Figures

Fig. 1.
The asymetric unit of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radii and the intramolecular hydrogen bond is shown as dashed lines.
Fig. 2.
Part of the crystal structure of (I), showing the formation of a cyclic R22(8) pattern. [Symmetry code: (i) x, y + 1, z + 1].

Crystal data

C11H8F3N3O2F(000) = 1104
Mr = 271.20Dx = 1.619 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3829 reflections
a = 9.757 (3) Åθ = 2.2–22.3°
b = 10.740 (3) ŵ = 0.15 mm1
c = 21.277 (6) ÅT = 125 K
β = 93.716 (3)°Flat needle, pale yellow
V = 2225 (1) Å30.30 × 0.18 × 0.05 mm
Z = 8

Data collection

Bruker APEXII CCD diffractometer3772 independent reflections
Radiation source: fine-focus sealed tube2737 reflections with I > 2σ(I)
graphiteRint = 0.072
[var phi] and ω scansθmax = 24.7°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1997)h = −11→11
Tmin = 0.957, Tmax = 0.993k = −12→12
20692 measured reflectionsl = −25→24

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.140w = 1/[σ2(Fo2) + (0.0233P)2 + 1.9621P] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
3772 reflectionsΔρmax = 0.43 e Å3
368 parametersΔρmin = −0.32 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0099 (12)

Special details

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)

xyzUiso*/Ueq
F11.0029 (2)0.57631 (18)0.86748 (8)0.0449 (5)
F20.88145 (19)0.61681 (17)0.94547 (8)0.0402 (5)
F31.03719 (18)0.74508 (17)0.91981 (8)0.0410 (5)
F510.5059 (2)0.47366 (17)0.12944 (8)0.0417 (5)
F520.62681 (18)0.41822 (16)0.05332 (8)0.0380 (5)
F530.43613 (17)0.32665 (16)0.06739 (7)0.0361 (5)
O10.8071 (2)0.8727 (2)0.96933 (9)0.0323 (5)
O20.6443 (2)0.98989 (19)0.91963 (9)0.0295 (5)
O510.6194 (2)0.1440 (2)0.01774 (9)0.0312 (5)
O520.7542 (2)0.00154 (19)0.06715 (9)0.0343 (5)
N10.7329 (2)0.7741 (2)0.76427 (10)0.0268 (6)
N20.8258 (2)0.6935 (2)0.79385 (10)0.0283 (6)
N30.5911 (3)0.9467 (2)0.78704 (13)0.0301 (6)
N510.7186 (2)0.2162 (2)0.22548 (10)0.0263 (6)
N520.6454 (3)0.3151 (2)0.19957 (10)0.0274 (6)
N530.8148 (3)0.0243 (3)0.19747 (13)0.0334 (7)
C10.6874 (3)0.7528 (3)0.70017 (12)0.0280 (7)
C20.6161 (3)0.6448 (3)0.68442 (13)0.0307 (7)
H20.59710.58590.71600.037*
C30.5730 (3)0.6233 (3)0.62231 (13)0.0340 (8)
H30.52440.54910.61110.041*
C40.6001 (3)0.7086 (3)0.57672 (14)0.0385 (8)
H40.57020.69320.53400.046*
C50.6705 (4)0.8163 (3)0.59258 (14)0.0412 (8)
H50.68860.87510.56080.049*
C60.7154 (3)0.8395 (3)0.65493 (13)0.0350 (8)
H60.76430.91350.66610.042*
C70.8382 (3)0.7328 (3)0.85250 (13)0.0269 (7)
C80.7540 (3)0.8365 (3)0.86272 (12)0.0258 (7)
C90.6881 (3)0.8604 (3)0.80423 (12)0.0253 (6)
C100.7303 (3)0.9061 (3)0.91922 (13)0.0265 (7)
C110.9388 (3)0.6684 (3)0.89644 (14)0.0333 (7)
C510.7711 (3)0.2189 (3)0.28986 (12)0.0258 (7)
C520.6897 (3)0.1791 (3)0.33664 (13)0.0303 (7)
H520.59970.14850.32640.036*
C530.7412 (3)0.1847 (3)0.39859 (14)0.0341 (7)
H530.68650.15720.43130.041*
C540.8717 (3)0.2301 (3)0.41322 (13)0.0344 (8)
H540.90600.23520.45600.041*
C550.9524 (3)0.2681 (3)0.36596 (14)0.0343 (7)
H551.04290.29760.37610.041*
C560.9021 (3)0.2632 (3)0.30386 (14)0.0319 (7)
H560.95700.29010.27120.038*
C570.6225 (3)0.2847 (3)0.13997 (12)0.0253 (6)
C580.6793 (3)0.1676 (3)0.12543 (12)0.0256 (7)
C590.7408 (3)0.1272 (3)0.18279 (12)0.0262 (7)
C600.6867 (3)0.0985 (3)0.06813 (13)0.0277 (7)
C610.5484 (3)0.3755 (3)0.09757 (13)0.0286 (7)
H10.792 (4)0.918 (4)1.004 (2)0.076 (14)*
H300.597 (4)0.987 (4)0.748 (2)0.066 (12)*
H310.579 (4)1.000 (3)0.8190 (17)0.047 (10)*
H510.628 (4)0.087 (4)−0.0156 (19)0.067 (12)*
H5300.830 (3)0.001 (3)0.2381 (17)0.041 (9)*
H5310.807 (4)−0.029 (3)0.1682 (18)0.047 (11)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F10.0527 (12)0.0511 (12)0.0302 (10)0.0212 (10)−0.0019 (8)−0.0080 (8)
F20.0541 (12)0.0421 (11)0.0240 (9)0.0044 (9)0.0002 (8)0.0061 (8)
F30.0383 (11)0.0534 (12)0.0302 (10)−0.0014 (9)−0.0061 (8)−0.0047 (8)
F510.0600 (12)0.0355 (11)0.0290 (10)0.0142 (9)−0.0017 (9)−0.0026 (8)
F520.0473 (11)0.0392 (11)0.0280 (9)−0.0021 (9)0.0055 (8)0.0098 (8)
F530.0368 (10)0.0450 (11)0.0255 (9)0.0005 (8)−0.0054 (8)0.0025 (8)
O10.0468 (13)0.0355 (13)0.0141 (10)0.0050 (10)−0.0018 (9)−0.0034 (9)
O20.0381 (12)0.0312 (12)0.0191 (10)0.0040 (10)0.0009 (8)−0.0016 (8)
O510.0446 (13)0.0341 (12)0.0145 (10)0.0059 (10)−0.0013 (9)−0.0016 (9)
O520.0547 (14)0.0304 (12)0.0171 (10)0.0095 (11)−0.0016 (9)−0.0027 (8)
N10.0323 (14)0.0339 (14)0.0140 (11)0.0015 (11)−0.0012 (10)−0.0020 (10)
N20.0310 (14)0.0353 (15)0.0184 (12)0.0013 (11)−0.0004 (10)−0.0021 (10)
N30.0386 (15)0.0329 (15)0.0187 (13)0.0037 (12)0.0008 (11)−0.0015 (12)
N510.0364 (14)0.0264 (13)0.0158 (12)0.0009 (11)−0.0012 (10)−0.0018 (10)
N520.0363 (14)0.0285 (14)0.0169 (12)0.0022 (11)−0.0016 (10)−0.0004 (10)
N530.0501 (17)0.0324 (16)0.0170 (14)0.0067 (13)−0.0026 (12)−0.0009 (12)
C10.0320 (16)0.0357 (18)0.0162 (14)0.0050 (14)0.0012 (12)−0.0017 (12)
C20.0316 (16)0.0389 (19)0.0212 (15)0.0045 (14)−0.0010 (12)−0.0017 (13)
C30.0328 (17)0.042 (2)0.0268 (16)0.0037 (15)−0.0016 (13)−0.0096 (14)
C40.0422 (19)0.051 (2)0.0219 (16)0.0123 (16)−0.0039 (14)−0.0082 (15)
C50.052 (2)0.050 (2)0.0224 (16)0.0114 (17)0.0047 (14)0.0059 (15)
C60.0403 (18)0.0407 (19)0.0243 (16)0.0009 (15)0.0036 (13)−0.0014 (14)
C70.0329 (16)0.0304 (17)0.0172 (14)−0.0030 (13)0.0007 (12)0.0010 (12)
C80.0346 (16)0.0274 (16)0.0153 (14)−0.0040 (13)0.0015 (12)−0.0009 (12)
C90.0300 (16)0.0262 (16)0.0200 (14)−0.0032 (13)0.0029 (12)−0.0019 (12)
C100.0352 (17)0.0258 (16)0.0183 (14)−0.0067 (14)0.0000 (12)0.0012 (12)
C110.0389 (18)0.0370 (18)0.0236 (16)0.0012 (15)−0.0002 (13)−0.0021 (14)
C510.0333 (16)0.0267 (16)0.0169 (14)0.0001 (13)−0.0028 (12)−0.0021 (12)
C520.0317 (16)0.0367 (18)0.0227 (15)0.0003 (14)0.0030 (12)0.0007 (13)
C530.0415 (19)0.0408 (19)0.0205 (15)0.0057 (15)0.0055 (13)0.0016 (13)
C540.0443 (19)0.0393 (19)0.0185 (15)0.0069 (15)−0.0074 (13)−0.0042 (13)
C550.0364 (18)0.0350 (19)0.0307 (17)−0.0008 (14)−0.0047 (14)−0.0044 (14)
C560.0370 (18)0.0348 (18)0.0242 (16)−0.0050 (14)0.0049 (13)−0.0027 (13)
C570.0336 (16)0.0254 (16)0.0168 (14)−0.0027 (13)0.0006 (12)−0.0002 (12)
C580.0360 (17)0.0243 (16)0.0164 (14)−0.0035 (13)0.0021 (12)−0.0008 (11)
C590.0318 (16)0.0280 (17)0.0191 (14)−0.0014 (13)0.0036 (12)−0.0015 (12)
C600.0362 (17)0.0297 (18)0.0170 (15)−0.0045 (14)0.0001 (12)−0.0013 (12)
C610.0359 (17)0.0289 (17)0.0209 (15)0.0004 (13)0.0015 (13)−0.0048 (12)

Geometric parameters (Å, °)

F1—C111.341 (3)C2—C31.380 (4)
F2—C111.336 (3)C2—H20.9500
F3—C111.336 (4)C3—C41.372 (5)
F51—C611.335 (3)C3—H30.9500
F52—C611.333 (3)C4—C51.376 (5)
F53—C611.340 (3)C4—H40.9500
O1—C101.313 (3)C5—C61.392 (4)
O1—H10.91 (4)C5—H50.9500
O2—C101.231 (3)C6—H60.9500
O51—C601.315 (3)C7—C81.410 (4)
O51—H510.94 (4)C7—C111.482 (4)
O52—C601.232 (4)C8—C91.387 (4)
N1—C91.350 (4)C8—C101.447 (4)
N1—N21.376 (3)C51—C561.379 (4)
N1—C11.425 (3)C51—C521.380 (4)
N2—C71.316 (4)C52—C531.381 (4)
N3—C91.358 (4)C52—H520.9500
N3—H300.95 (4)C53—C541.381 (5)
N3—H310.90 (4)C53—H530.9500
N51—C591.346 (4)C54—C551.378 (4)
N51—N521.376 (3)C54—H540.9500
N51—C511.431 (3)C55—C561.380 (4)
N52—C571.315 (3)C55—H550.9500
N53—C591.346 (4)C56—H560.9500
N53—H5300.90 (3)C57—C581.416 (4)
N53—H5310.85 (4)C57—C611.484 (4)
C1—C61.379 (4)C58—C591.393 (4)
C1—C21.383 (4)C58—C601.433 (4)
C10—O1—H1114 (3)O2—C10—C8121.9 (3)
C60—O51—H51108 (2)O1—C10—C8114.9 (3)
C9—N1—N2112.0 (2)F2—C11—F3107.0 (2)
C9—N1—C1128.2 (2)F2—C11—F1106.6 (2)
N2—N1—C1119.5 (2)F3—C11—F1106.3 (2)
C7—N2—N1104.4 (2)F2—C11—C7113.1 (3)
C9—N3—H30118 (2)F3—C11—C7112.2 (3)
C9—N3—H31110 (2)F1—C11—C7111.3 (2)
H30—N3—H31114 (3)C56—C51—C52121.3 (3)
C59—N51—N52112.3 (2)C56—C51—N51118.9 (3)
C59—N51—C51126.7 (2)C52—C51—N51119.8 (3)
N52—N51—C51120.8 (2)C51—C52—C53119.0 (3)
C57—N52—N51104.2 (2)C51—C52—H52120.5
C59—N53—H530120 (2)C53—C52—H52120.5
C59—N53—H531111 (2)C54—C53—C52120.2 (3)
H530—N53—H531121 (3)C54—C53—H53119.9
C6—C1—C2121.1 (3)C52—C53—H53119.9
C6—C1—N1119.8 (3)C55—C54—C53120.2 (3)
C2—C1—N1119.1 (3)C55—C54—H54119.9
C3—C2—C1119.3 (3)C53—C54—H54119.9
C3—C2—H2120.3C54—C55—C56120.2 (3)
C1—C2—H2120.3C54—C55—H55119.9
C4—C3—C2120.3 (3)C56—C55—H55119.9
C4—C3—H3119.9C51—C56—C55119.2 (3)
C2—C3—H3119.9C51—C56—H56120.4
C3—C4—C5120.3 (3)C55—C56—H56120.4
C3—C4—H4119.9N52—C57—C58112.8 (2)
C5—C4—H4119.9N52—C57—C61117.9 (2)
C4—C5—C6120.3 (3)C58—C57—C61129.2 (2)
C4—C5—H5119.8C59—C58—C57103.7 (2)
C6—C5—H5119.8C59—C58—C60122.8 (3)
C1—C6—C5118.7 (3)C57—C58—C60133.5 (3)
C1—C6—H6120.6N51—C59—N53122.3 (3)
C5—C6—H6120.6N51—C59—C58107.0 (2)
N2—C7—C8112.4 (2)N53—C59—C58130.7 (3)
N2—C7—C11117.7 (3)O52—C60—O51122.6 (3)
C8—C7—C11129.8 (3)O52—C60—C58120.5 (3)
C9—C8—C7104.4 (2)O51—C60—C58116.8 (3)
C9—C8—C10124.1 (3)F52—C61—F51107.4 (2)
C7—C8—C10131.5 (3)F52—C61—F53106.6 (2)
N1—C9—N3123.2 (3)F51—C61—F53106.3 (2)
N1—C9—C8106.7 (2)F52—C61—C57112.1 (2)
N3—C9—C8130.0 (3)F51—C61—C57111.5 (2)
O2—C10—O1123.2 (3)F53—C61—C57112.7 (2)
C9—N1—N2—C7−0.7 (3)N2—C7—C11—F1−0.1 (4)
C1—N1—N2—C7−175.4 (2)C8—C7—C11—F1−177.2 (3)
C59—N51—N52—C570.2 (3)C59—N51—C51—C5683.1 (4)
C51—N51—N52—C57175.8 (2)N52—N51—C51—C56−91.7 (3)
C9—N1—C1—C669.0 (4)C59—N51—C51—C52−97.9 (4)
N2—N1—C1—C6−117.2 (3)N52—N51—C51—C5287.3 (3)
C9—N1—C1—C2−111.3 (3)C56—C51—C52—C530.3 (5)
N2—N1—C1—C262.5 (4)N51—C51—C52—C53−178.7 (3)
C6—C1—C2—C30.3 (4)C51—C52—C53—C540.4 (5)
N1—C1—C2—C3−179.4 (3)C52—C53—C54—C55−1.2 (5)
C1—C2—C3—C4−0.3 (4)C53—C54—C55—C561.3 (5)
C2—C3—C4—C50.0 (5)C52—C51—C56—C55−0.1 (5)
C3—C4—C5—C60.3 (5)N51—C51—C56—C55178.9 (3)
C2—C1—C6—C50.0 (5)C54—C55—C56—C51−0.6 (5)
N1—C1—C6—C5179.6 (3)N51—N52—C57—C58−0.2 (3)
C4—C5—C6—C1−0.3 (5)N51—N52—C57—C61−177.9 (2)
N1—N2—C7—C80.9 (3)N52—C57—C58—C590.1 (3)
N1—N2—C7—C11−176.6 (2)C61—C57—C58—C59177.5 (3)
N2—C7—C8—C9−0.8 (3)N52—C57—C58—C60−176.8 (3)
C11—C7—C8—C9176.3 (3)C61—C57—C58—C600.6 (5)
N2—C7—C8—C10177.1 (3)N52—N51—C59—N53177.5 (3)
C11—C7—C8—C10−5.7 (5)C51—N51—C59—N532.2 (5)
N2—N1—C9—N3−176.8 (3)N52—N51—C59—C58−0.2 (3)
C1—N1—C9—N3−2.6 (5)C51—N51—C59—C58−175.4 (3)
N2—N1—C9—C80.2 (3)C57—C58—C59—N510.1 (3)
C1—N1—C9—C8174.3 (3)C60—C58—C59—N51177.4 (3)
C7—C8—C9—N10.4 (3)C57—C58—C59—N53−177.3 (3)
C10—C8—C9—N1−177.8 (3)C60—C58—C59—N530.0 (5)
C7—C8—C9—N3177.0 (3)C59—C58—C60—O52−3.2 (5)
C10—C8—C9—N3−1.1 (5)C57—C58—C60—O52173.2 (3)
C9—C8—C10—O22.9 (5)C59—C58—C60—O51177.1 (3)
C7—C8—C10—O2−174.7 (3)C57—C58—C60—O51−6.4 (5)
C9—C8—C10—O1−177.2 (3)N52—C57—C61—F52115.3 (3)
C7—C8—C10—O15.2 (5)C58—C57—C61—F52−62.0 (4)
N2—C7—C11—F2−120.1 (3)N52—C57—C61—F51−5.1 (4)
C8—C7—C11—F262.9 (4)C58—C57—C61—F51177.6 (3)
N2—C7—C11—F3118.8 (3)N52—C57—C61—F53−124.5 (3)
C8—C7—C11—F3−58.2 (4)C58—C57—C61—F5358.2 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N53—H531···O520.85 (4)2.20 (4)2.808 (3)128 (3)
O51—H51···O2i0.94 (4)1.75 (4)2.687 (3)177 (4)
N3—H31···O20.90 (4)2.20 (4)2.873 (3)132 (3)
O1—H1···O52ii0.91 (4)1.67 (4)2.580 (3)176 (4)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2218).

References

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