#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:11:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178424 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/45/4024582.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4024582
loop_
_publ_author_name
'Nugzar Ghavtadze'
'Roland Fröhlich'
'Ernst-Ulrich Würthwein'
_publ_section_title
;
Acid-Mediated Electrocyclic Domino Transformations of 5,5-Disubstituted
1-Amino-1-azapenta-1,4-dien-3-ones into Dihydrospiroindenepyrazole and
Dihydroindenodiazepine Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4584
_journal_page_last               4591
_journal_paper_doi               10.1021/jo900270e
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C19 H15 F3 N2'
_chemical_formula_weight         328.33
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.061(2)
_cell_angle_beta                 94.523(2)
_cell_angle_gamma                101.547(4)
_cell_formula_units_Z            4
_cell_length_a                   10.2968(5)
_cell_length_b                   11.3686(5)
_cell_length_c                   14.3731(8)
_cell_measurement_reflns_used    5199
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      0.88
_cell_volume                     1599.24(14)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SCHAKAL (Keller, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.068
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22644
_diffrn_reflns_theta_full        67.97
_diffrn_reflns_theta_max         67.97
_diffrn_reflns_theta_min         4.42
_exptl_absorpt_coefficient_mu    0.890
_exptl_absorpt_correction_T_max  0.9738
_exptl_absorpt_correction_T_min  0.7761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         5612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0666
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ2^(Fo2^)+(0.0590P)2^+2.5454P] where P=(Fo2+2Fc2)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1688
_refine_ls_wR_factor_ref         0.1802
_reflns_number_gt                4457
_reflns_number_total             5612
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900270e_si_007.cif
_cod_data_source_block           wue4380
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4024582
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.7336(3) 1.2423(3) 0.2774(2) 0.0494(8) Uani 1 1 d . . .
H1A1 H 0.8160 1.3065 0.2967 0.059 Uiso 1 1 calc R . .
H1A2 H 0.7146 1.2074 0.3330 0.059 Uiso 1 1 calc R . .
N2A N 0.7578(3) 1.1439(3) 0.2000(2) 0.0444(6) Uani 1 1 d . . .
C3A C 0.7695(3) 1.1810(3) 0.1090(2) 0.0493(8) Uani 1 1 d . . .
H3A1 H 0.8013 1.1195 0.0646 0.074 Uiso 1 1 calc R . .
H3A2 H 0.8323 1.2599 0.1198 0.074 Uiso 1 1 calc R . .
H3A3 H 0.6828 1.1881 0.0821 0.074 Uiso 1 1 calc R . .
N4A N 0.6636(3) 1.0306(3) 0.1869(2) 0.0464(7) Uani 1 1 d . . .
H4A H 0.702(4) 0.965(3) 0.194(3) 0.056 Uiso 1 1 d . . .
C5A C 0.5305(3) 1.0075(3) 0.1640(2) 0.0384(7) Uani 1 1 d . . .
C6A C 0.4563(3) 1.0967(3) 0.1676(2) 0.0368(7) Uani 1 1 d . . .
C7A C 0.3178(3) 1.0753(3) 0.1285(2) 0.0401(7) Uani 1 1 d . . .
H7A H 0.2627 0.9977 0.0994 0.048 Uiso 1 1 calc R . .
C8A C 0.2792(3) 1.1850(3) 0.1402(2) 0.0414(7) Uani 1 1 d . . .
C9A C 0.3911(3) 1.2842(3) 0.1882(2) 0.0392(7) Uani 1 1 d . . .
C10A C 0.4050(4) 1.4112(3) 0.2167(2) 0.0483(8) Uani 1 1 d . . .
H10A H 0.3327 1.4478 0.2058 0.058 Uiso 1 1 calc R . .
C11A C 0.5281(4) 1.4824(3) 0.2615(3) 0.0568(9) Uani 1 1 d . . .
H11A H 0.5397 1.5685 0.2806 0.068 Uiso 1 1 calc R . .
C12A C 0.6342(4) 1.4286(3) 0.2787(3) 0.0519(9) Uani 1 1 d . . .
H12A H 0.7169 1.4794 0.3084 0.062 Uiso 1 1 calc R . .
C13A C 0.6220(3) 1.3019(3) 0.2532(2) 0.0426(7) Uani 1 1 d . . .
C14A C 0.4993(3) 1.2294(3) 0.2056(2) 0.0367(7) Uani 1 1 d . . .
C15A C 0.4685(3) 0.8729(3) 0.1302(2) 0.0376(7) Uani 1 1 d . . .
C16A C 0.5266(3) 0.7988(3) 0.0636(2) 0.0452(8) Uani 1 1 d . . .
H16A H 0.6062 0.8334 0.0422 0.054 Uiso 1 1 calc R . .
C17A C 0.4688(4) 0.6752(3) 0.0288(3) 0.0541(9) Uani 1 1 d . . .
H17A H 0.5084 0.6260 -0.0165 0.065 Uiso 1 1 calc R . .
C18A C 0.3530(4) 0.6242(3) 0.0607(3) 0.0570(9) Uani 1 1 d . . .
H18A H 0.3131 0.5402 0.0368 0.068 Uiso 1 1 calc R . .
C19A C 0.2949(4) 0.6959(3) 0.1277(3) 0.0582(10) Uani 1 1 d . . .
H19A H 0.2157 0.6604 0.1493 0.070 Uiso 1 1 calc R . .
C20A C 0.3527(3) 0.8195(3) 0.1630(3) 0.0486(8) Uani 1 1 d . . .
H20A H 0.3137 0.8676 0.2095 0.058 Uiso 1 1 calc R . .
C21A C 0.1461(4) 1.2010(3) 0.1116(3) 0.0534(9) Uani 1 1 d . . .
F22A F 0.1454(3) 1.2860(3) 0.0589(2) 0.0993(10) Uani 1 1 d . . .
F23A F 0.0831(2) 1.2418(2) 0.18625(17) 0.0676(6) Uani 1 1 d . . .
F24A F 0.0650(3) 1.0994(3) 0.0616(3) 0.1249(15) Uani 1 1 d . . .
C1B C -0.1141(3) 0.7904(3) 0.1888(2) 0.0477(8) Uani 1 1 d . . .
H1B1 H -0.0615 0.8281 0.1444 0.057 Uiso 1 1 calc R . .
H1B2 H -0.1922 0.7313 0.1506 0.057 Uiso 1 1 calc R . .
N2B N -0.1609(2) 0.8877(2) 0.25318(19) 0.0426(6) Uani 1 1 d . . .
C3B C -0.2269(4) 0.8456(3) 0.3311(3) 0.0532(9) Uani 1 1 d . . .
H3B1 H -0.1609 0.8302 0.3765 0.080 Uiso 1 1 calc R . .
H3B2 H -0.2937 0.7701 0.3048 0.080 Uiso 1 1 calc R . .
H3B3 H -0.2694 0.9085 0.3636 0.080 Uiso 1 1 calc R . .
N4B N -0.0625(3) 0.9980(2) 0.2892(2) 0.0416(6) Uani 1 1 d . . .
H4B H -0.086(3) 1.065(3) 0.270(3) 0.050 Uiso 1 1 d . . .
C5B C 0.0565(3) 1.0119(3) 0.3410(2) 0.0359(6) Uani 1 1 d . . .
C6B C 0.1153(3) 0.9165(3) 0.3541(2) 0.0366(7) Uani 1 1 d . . .
C7B C 0.2338(3) 0.9298(3) 0.4202(2) 0.0384(7) Uani 1 1 d . . .
H7B H 0.2840 1.0048 0.4590 0.046 Uiso 1 1 calc R . .
C8B C 0.2610(3) 0.8169(3) 0.4175(2) 0.0401(7) Uani 1 1 d . . .
C9B C 0.1607(3) 0.7232(3) 0.3496(2) 0.0402(7) Uani 1 1 d . . .
C10B C 0.1407(3) 0.5949(3) 0.3212(3) 0.0491(8) Uani 1 1 d . . .
H10B H 0.1984 0.5527 0.3477 0.059 Uiso 1 1 calc R . .
C11B C 0.0339(4) 0.5318(3) 0.2531(3) 0.0549(9) Uani 1 1 d . . .
H11B H 0.0172 0.4453 0.2346 0.066 Uiso 1 1 calc R . .
C12B C -0.0501(4) 0.5938(3) 0.2109(3) 0.0531(9) Uani 1 1 d . . .
H12B H -0.1209 0.5483 0.1637 0.064 Uiso 1 1 calc R . .
C13B C -0.0312(3) 0.7210(3) 0.2373(2) 0.0431(7) Uani 1 1 d . . .
C14B C 0.0729(3) 0.7856(3) 0.3102(2) 0.0384(7) Uani 1 1 d . . .
C15B C 0.1193(3) 1.1427(3) 0.3877(2) 0.0364(7) Uani 1 1 d . . .
C16B C 0.0453(4) 1.2170(3) 0.4397(2) 0.0472(8) Uani 1 1 d . . .
H16B H -0.0448 1.1845 0.4444 0.057 Uiso 1 1 calc R . .
C17B C 0.1031(4) 1.3380(3) 0.4843(3) 0.0588(10) Uani 1 1 d . . .
H17B H 0.0527 1.3874 0.5199 0.071 Uiso 1 1 calc R . .
C18B C 0.2358(4) 1.3869(3) 0.4767(3) 0.0575(10) Uani 1 1 d . . .
H18B H 0.2750 1.4696 0.5066 0.069 Uiso 1 1 calc R . .
C19B C 0.3095(4) 1.3141(3) 0.4254(3) 0.0535(9) Uani 1 1 d . . .
H19B H 0.3994 1.3471 0.4206 0.064 Uiso 1 1 calc R . .
C20B C 0.2521(3) 1.1925(3) 0.3807(2) 0.0433(7) Uani 1 1 d . . .
H20B H 0.3031 1.1434 0.3455 0.052 Uiso 1 1 calc R . .
C21B C 0.3803(3) 0.7948(3) 0.4684(3) 0.0498(8) Uani 1 1 d . . .
F22B F 0.3536(2) 0.69500(19) 0.50614(17) 0.0684(6) Uani 1 1 d . . .
F23B F 0.4756(2) 0.7771(3) 0.4129(2) 0.0943(9) Uani 1 1 d . . .
F24B F 0.4391(2) 0.8882(2) 0.54247(18) 0.0702(7) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2A C1A C13A 115.8(3) . . ?
N4A N2A C3A 110.8(3) . . ?
N4A N2A C1A 113.4(3) . . ?
C3A N2A C1A 113.1(3) . . ?
C5A N4A N2A 128.4(3) . . ?
N4A C5A C6A 124.8(3) . . ?
N4A C5A C15A 113.0(3) . . ?
C6A C5A C15A 122.2(3) . . ?
C5A C6A C7A 125.5(3) . . ?
C5A C6A C14A 128.7(3) . . ?
C7A C6A C14A 105.7(3) . . ?
C8A C7A C6A 109.6(3) . . ?
C7A C8A C9A 109.3(3) . . ?
C7A C8A C21A 125.9(3) . . ?
C9A C8A C21A 124.8(3) . . ?
C10A C9A C14A 120.7(3) . . ?
C10A C9A C8A 132.4(3) . . ?
C14A C9A C8A 106.9(3) . . ?
C11A C10A C9A 118.3(3) . . ?
C12A C11A C10A 121.0(3) . . ?
C11A C12A C13A 121.9(3) . . ?
C12A C13A C14A 117.7(3) . . ?
C12A C13A C1A 122.2(3) . . ?
C14A C13A C1A 120.2(3) . . ?
C13A C14A C9A 120.5(3) . . ?
C13A C14A C6A 131.0(3) . . ?
C9A C14A C6A 108.5(3) . . ?
C20A C15A C16A 118.8(3) . . ?
C20A C15A C5A 121.5(3) . . ?
C16A C15A C5A 119.7(3) . . ?
C17A C16A C15A 120.8(3) . . ?
C18A C17A C16A 119.7(3) . . ?
C17A C18A C19A 120.4(3) . . ?
C18A C19A C20A 120.2(3) . . ?
C19A C20A C15A 120.2(3) . . ?
F24A C21A F23A 105.6(3) . . ?
F24A C21A F22A 106.3(3) . . ?
F23A C21A F22A 103.2(3) . . ?
F24A C21A C8A 113.7(3) . . ?
F23A C21A C8A 113.3(3) . . ?
F22A C21A C8A 113.8(3) . . ?
N2B C1B C13B 115.5(3) . . ?
N4B N2B C3B 111.0(3) . . ?
N4B N2B C1B 114.3(2) . . ?
C3B N2B C1B 113.5(3) . . ?
C5B N4B N2B 127.7(3) . . ?
N4B C5B C6B 125.1(3) . . ?
N4B C5B C15B 113.1(3) . . ?
C6B C5B C15B 121.7(3) . . ?
C5B C6B C7B 125.0(3) . . ?
C5B C6B C14B 129.2(3) . . ?
C7B C6B C14B 105.8(3) . . ?
C8B C7B C6B 109.4(3) . . ?
C7B C8B C9B 109.4(3) . . ?
C7B C8B C21B 125.1(3) . . ?
C9B C8B C21B 125.3(3) . . ?
C10B C9B C14B 120.6(3) . . ?
C10B C9B C8B 132.8(3) . . ?
C14B C9B C8B 106.6(3) . . ?
C11B C10B C9B 118.2(3) . . ?
C10B C11B C12B 121.4(3) . . ?
C13B C12B C11B 121.4(3) . . ?
C12B C13B C14B 117.8(3) . . ?
C12B C13B C1B 122.4(3) . . ?
C14B C13B C1B 119.8(3) . . ?
C13B C14B C9B 120.6(3) . . ?
C13B C14B C6B 130.6(3) . . ?
C9B C14B C6B 108.8(3) . . ?
C16B C15B C20B 119.1(3) . . ?
C16B C15B C5B 120.0(3) . . ?
C20B C15B C5B 120.9(3) . . ?
C17B C16B C15B 120.4(3) . . ?
C16B C17B C18B 120.0(4) . . ?
C19B C18B C17B 119.9(3) . . ?
C18B C19B C20B 120.4(3) . . ?
C19B C20B C15B 120.2(3) . . ?
F23B C21B F24B 105.5(3) . . ?
F23B C21B F22B 105.8(3) . . ?
F24B C21B F22B 105.0(3) . . ?
F23B C21B C8B 113.5(3) . . ?
F24B C21B C8B 113.3(3) . . ?
F22B C21B C8B 113.0(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A N2A 1.480(4) . ?
C1A C13A 1.500(5) . ?
N2A N4A 1.416(4) . ?
N2A C3A 1.463(4) . ?
N4A C5A 1.343(4) . ?
C5A C6A 1.382(4) . ?
C5A C15A 1.494(4) . ?
C6A C7A 1.444(4) . ?
C6A C14A 1.457(4) . ?
C7A C8A 1.364(4) . ?
C8A C9A 1.450(4) . ?
C8A C21A 1.458(5) . ?
C9A C10A 1.392(4) . ?
C9A C14A 1.411(4) . ?
C10A C11A 1.385(5) . ?
C11A C12A 1.385(5) . ?
C12A C13A 1.387(5) . ?
C13A C14A 1.397(4) . ?
C15A C20A 1.390(4) . ?
C15A C16A 1.392(4) . ?
C16A C17A 1.380(5) . ?
C17A C18A 1.374(5) . ?
C18A C19A 1.381(5) . ?
C19A C20A 1.381(5) . ?
C21A F24A 1.311(4) . ?
C21A F23A 1.345(4) . ?
C21A F22A 1.347(5) . ?
C1B N2B 1.473(4) . ?
C1B C13B 1.497(5) . ?
N2B N4B 1.416(3) . ?
N2B C3B 1.470(4) . ?
N4B C5B 1.345(4) . ?
C5B C6B 1.381(4) . ?
C5B C15B 1.487(4) . ?
C6B C7B 1.448(4) . ?
C6B C14B 1.452(4) . ?
C7B C8B 1.361(4) . ?
C8B C9B 1.457(4) . ?
C8B C21B 1.471(5) . ?
C9B C10B 1.398(4) . ?
C9B C14B 1.410(4) . ?
C10B C11B 1.379(5) . ?
C11B C12B 1.397(5) . ?
C12B C13B 1.385(5) . ?
C13B C14B 1.404(4) . ?
C15B C16B 1.392(4) . ?
C15B C20B 1.392(4) . ?
C16B C17B 1.379(5) . ?
C17B C18B 1.391(6) . ?
C18B C19B 1.374(5) . ?
C19B C20B 1.383(5) . ?
C21B F23B 1.332(4) . ?
C21B F24B 1.340(4) . ?
C21B F22B 1.347(4) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13A C1A N2A N4A -76.8(4) . . . . ?
C13A C1A N2A C3A 50.3(4) . . . . ?
C3A N2A N4A C5A -68.5(4) . . . . ?
C1A N2A N4A C5A 59.8(4) . . . . ?
N2A N4A C5A C6A -13.8(5) . . . . ?
N2A N4A C5A C15A 164.2(3) . . . . ?
N4A C5A C6A C7A 168.9(3) . . . . ?
C15A C5A C6A C7A -8.8(5) . . . . ?
N4A C5A C6A C14A -7.7(5) . . . . ?
C15A C5A C6A C14A 174.6(3) . . . . ?
C5A C6A C7A C8A -176.6(3) . . . . ?
C14A C6A C7A C8A 0.7(4) . . . . ?
C6A C7A C8A C9A -0.2(4) . . . . ?
C6A C7A C8A C21A -178.8(3) . . . . ?
C7A C8A C9A C10A -180.0(3) . . . . ?
C21A C8A C9A C10A -1.4(6) . . . . ?
C7A C8A C9A C14A -0.4(4) . . . . ?
C21A C8A C9A C14A 178.2(3) . . . . ?
C14A C9A C10A C11A 0.7(5) . . . . ?
C8A C9A C10A C11A -179.7(3) . . . . ?
C9A C10A C11A C12A -0.8(5) . . . . ?
C10A C11A C12A C13A -0.9(6) . . . . ?
C11A C12A C13A C14A 2.5(5) . . . . ?
C11A C12A C13A C1A -175.8(3) . . . . ?
N2A C1A C13A C12A -136.4(3) . . . . ?
N2A C1A C13A C14A 45.4(4) . . . . ?
C12A C13A C14A C9A -2.5(5) . . . . ?
C1A C13A C14A C9A 175.8(3) . . . . ?
C12A C13A C14A C6A 178.1(3) . . . . ?
C1A C13A C14A C6A -3.6(5) . . . . ?
C10A C9A C14A C13A 0.9(5) . . . . ?
C8A C9A C14A C13A -178.7(3) . . . . ?
C10A C9A C14A C6A -179.5(3) . . . . ?
C8A C9A C14A C6A 0.8(3) . . . . ?
C5A C6A C14A C13A -4.3(6) . . . . ?
C7A C6A C14A C13A 178.6(3) . . . . ?
C5A C6A C14A C9A 176.2(3) . . . . ?
C7A C6A C14A C9A -0.9(3) . . . . ?
N4A C5A C15A C20A 134.8(3) . . . . ?
C6A C5A C15A C20A -47.2(5) . . . . ?
N4A C5A C15A C16A -45.7(4) . . . . ?
C6A C5A C15A C16A 132.3(3) . . . . ?
C20A C15A C16A C17A 1.7(5) . . . . ?
C5A C15A C16A C17A -177.8(3) . . . . ?
C15A C16A C17A C18A -0.5(5) . . . . ?
C16A C17A C18A C19A -0.4(6) . . . . ?
C17A C18A C19A C20A 0.1(6) . . . . ?
C18A C19A C20A C15A 1.1(6) . . . . ?
C16A C15A C20A C19A -2.0(5) . . . . ?
C5A C15A C20A C19A 177.5(3) . . . . ?
C7A C8A C21A F24A -7.5(6) . . . . ?
C9A C8A C21A F24A 174.1(4) . . . . ?
C7A C8A C21A F23A 113.1(4) . . . . ?
C9A C8A C21A F23A -65.3(5) . . . . ?
C7A C8A C21A F22A -129.3(4) . . . . ?
C9A C8A C21A F22A 52.3(5) . . . . ?
C13B C1B N2B N4B 77.7(4) . . . . ?
C13B C1B N2B C3B -50.9(4) . . . . ?
C3B N2B N4B C5B 71.4(4) . . . . ?
C1B N2B N4B C5B -58.5(4) . . . . ?
N2B N4B C5B C6B 12.4(5) . . . . ?
N2B N4B C5B C15B -165.3(3) . . . . ?
N4B C5B C6B C7B -170.9(3) . . . . ?
C15B C5B C6B C7B 6.6(5) . . . . ?
N4B C5B C6B C14B 6.6(5) . . . . ?
C15B C5B C6B C14B -175.9(3) . . . . ?
C5B C6B C7B C8B 177.6(3) . . . . ?
C14B C6B C7B C8B -0.4(3) . . . . ?
C6B C7B C8B C9B -0.4(4) . . . . ?
C6B C7B C8B C21B 174.2(3) . . . . ?
C7B C8B C9B C10B -178.7(3) . . . . ?
C21B C8B C9B C10B 6.6(6) . . . . ?
C7B C8B C9B C14B 1.0(4) . . . . ?
C21B C8B C9B C14B -173.6(3) . . . . ?
C14B C9B C10B C11B 0.7(5) . . . . ?
C8B C9B C10B C11B -179.6(3) . . . . ?
C9B C10B C11B C12B 2.0(5) . . . . ?
C10B C11B C12B C13B -1.4(6) . . . . ?
C11B C12B C13B C14B -2.0(5) . . . . ?
C11B C12B C13B C1B 175.9(3) . . . . ?
N2B C1B C13B C12B 135.8(3) . . . . ?
N2B C1B C13B C14B -46.3(4) . . . . ?
C12B C13B C14B C9B 4.6(5) . . . . ?
C1B C13B C14B C9B -173.3(3) . . . . ?
C12B C13B C14B C6B -178.6(3) . . . . ?
C1B C13B C14B C6B 3.4(5) . . . . ?
C10B C9B C14B C13B -4.1(5) . . . . ?
C8B C9B C14B C13B 176.1(3) . . . . ?
C10B C9B C14B C6B 178.6(3) . . . . ?
C8B C9B C14B C6B -1.3(3) . . . . ?
C5B C6B C14B C13B 6.1(6) . . . . ?
C7B C6B C14B C13B -176.0(3) . . . . ?
C5B C6B C14B C9B -176.9(3) . . . . ?
C7B C6B C14B C9B 1.0(3) . . . . ?
N4B C5B C15B C16B 48.9(4) . . . . ?
C6B C5B C15B C16B -128.8(3) . . . . ?
N4B C5B C15B C20B -131.3(3) . . . . ?
C6B C5B C15B C20B 51.0(4) . . . . ?
C20B C15B C16B C17B -0.6(5) . . . . ?
C5B C15B C16B C17B 179.2(3) . . . . ?
C15B C16B C17B C18B 0.7(5) . . . . ?
C16B C17B C18B C19B -0.6(6) . . . . ?
C17B C18B C19B C20B 0.4(5) . . . . ?
C18B C19B C20B C15B -0.3(5) . . . . ?
C16B C15B C20B C19B 0.4(5) . . . . ?
C5B C15B C20B C19B -179.4(3) . . . . ?
C7B C8B C21B F23B -99.2(4) . . . . ?
C9B C8B C21B F23B 74.6(4) . . . . ?
C7B C8B C21B F24B 21.0(5) . . . . ?
C9B C8B C21B F24B -165.2(3) . . . . ?
C7B C8B C21B F22B 140.3(3) . . . . ?
C9B C8B C21B F22B -45.9(5) . . . . ?
