#------------------------------------------------------------------------------
#$Date: 2024-12-06 18:47:05 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296406 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/24/1572482.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_1572482
loop_
_publ_author_name
'Chen, Kaixin'
'Lin, Jie'
'Jing, Jing'
'Wang, Junda'
'Hu, Jiayu'
'Yi, Hong'
'Lei, Aiwen'
'Li, Jie'
_publ_section_title
;
 Cobalt-catalyzed conformationally restricted alkylarylation enables
 divergent access to Csp³-rich N-heterocycles.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              16250
_journal_page_last               16258
_journal_paper_doi               10.1039/d4sc04056b
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C23 H22 Cl F3 N2'
_chemical_formula_sum            'C23 H22 Cl F3 N2'
_chemical_formula_weight         418.87
_chemical_name_systematic
1-(4-chlorobenzyl)-3,3-difluoro-3a-(4-fluorobenzyl)octahydro-1H-indole-2-carbonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-02-02 deposited with the CCDC.	2024-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.393(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.175(2)
_cell_length_b                   8.8838(10)
_cell_length_c                   16.016(3)
_cell_measurement_reflns_used    3629
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      26.4070
_cell_measurement_theta_min      2.5600
_cell_volume                     2024.6(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      220(2)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10642
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.544
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4103
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0575P)²+0.1367P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1324
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2714
_reflns_number_total             4103
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc04056b2.cif
_cod_data_source_block           test1
_cod_depositor_comments
'Adding full bibliography for 1572482--1572485.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1572482
_shelx_shelxl_version_number     2019/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.876
_shelx_estimated_absorpt_t_max   0.935
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.76390(9) 0.35353(15) 0.32173(11) 0.0631(4) Uani 1 1 d . . . . .
N1 N 0.67994(10) 0.0317(2) 0.32123(12) 0.0418(4) Uani 1 1 d . . . . .
C1 C 0.57769(14) 0.0124(3) 0.27535(16) 0.0509(6) Uani 1 1 d . . . . .
H1A H 0.5569(4) -0.0471(10) 0.2156(10) 0.061 Uiso 1 1 calc R U . . .
H1B H 0.5469(5) 0.1136(17) 0.2575(4) 0.061 Uiso 1 1 calc R U . . .
Cl1 Cl 0.44368(4) -0.31859(7) 0.51738(5) 0.0605(2) Uani 1 1 d . . . . .
F2 F 0.87022(9) 0.26477(18) 0.45681(10) 0.0647(4) Uani 1 1 d . . . . .
N2 N 0.76682(14) 0.0820(3) 0.56220(16) 0.0624(6) Uani 1 1 d . . . . .
C2 C 0.54559(13) -0.0671(3) 0.33860(15) 0.0414(5) Uani 1 1 d . . . . .
F3 F 1.21132(9) 0.46749(18) 0.47592(11) 0.0699(4) Uani 1 1 d . . . . .
C3 C 0.59738(15) -0.1848(3) 0.39670(16) 0.0459(6) Uani 1 1 d . . . . .
H3 H 0.6581(14) -0.2146(7) 0.39877(16) 0.055 Uiso 1 1 calc R U . . .
C4 C 0.56675(15) -0.2617(3) 0.45182(17) 0.0469(6) Uani 1 1 d . . . . .
H4 H 0.6031(10) -0.343(2) 0.4918(11) 0.056 Uiso 1 1 calc R U . . .
C5 C 0.48300(14) -0.2198(3) 0.44864(16) 0.0436(5) Uani 1 1 d . . . . .
C6 C 0.42996(15) -0.1041(3) 0.39190(17) 0.0488(6) Uani 1 1 d . . . . .
H6 H 0.3732(14) -0.0768(7) 0.39018(17) 0.059 Uiso 1 1 calc R U . . .
C7 C 0.46185(14) -0.0283(3) 0.33707(17) 0.0472(6) Uani 1 1 d . . . . .
H7 H 0.4261(9) 0.051(2) 0.2982(10) 0.057 Uiso 1 1 calc R U . . .
C8 C 0.72092(14) 0.0417(3) 0.25555(15) 0.0407(5) Uani 1 1 d . . . . .
H8 H 0.6857(9) 0.1118(18) 0.2064(12) 0.049 Uiso 1 1 calc R U . . .
C17 C 0.86392(14) 0.1742(3) 0.26041(16) 0.0438(5) Uani 1 1 d . . . . .
H17A H 0.87185(18) 0.0950(13) 0.2242(6) 0.053 Uiso 1 1 calc R U . . .
H17B H 0.8203(7) 0.2451(11) 0.2163(7) 0.053 Uiso 1 1 calc R U . . .
C18 C 0.95745(14) 0.2524(3) 0.31676(15) 0.0404(5) Uani 1 1 d . . . . .
C9 C 0.72161(16) -0.1096(3) 0.21176(18) 0.0527(6) Uani 1 1 d . . . . .
H9A H 0.6576(11) -0.1496(7) 0.1798(6) 0.063 Uiso 1 1 calc R U . . .
H9B H 0.7420(3) -0.0950(4) 0.1638(8) 0.063 Uiso 1 1 calc R U . . .
C10 C 0.78565(18) -0.2239(3) 0.2840(2) 0.0626(7) Uani 1 1 d . . . . .
H10A H 0.78816(18) -0.3138(18) 0.2516(6) 0.075 Uiso 1 1 calc R U . . .
H10B H 0.7604(5) -0.2506(6) 0.3257(8) 0.075 Uiso 1 1 calc R U . . .
C11 C 0.88435(17) -0.1613(3) 0.34223(19) 0.0564(7) Uani 1 1 d . . . . .
H11A H 0.9136(6) -0.1441(4) 0.2996(8) 0.068 Uiso 1 1 calc R U . . .
H11B H 0.9243(8) -0.2370(14) 0.3923(9) 0.068 Uiso 1 1 calc R U . . .
C12 C 0.88268(14) -0.0137(3) 0.38974(15) 0.0434(5) Uani 1 1 d . . . . .
H12A H 0.9472(10) 0.0257(7) 0.4246(6) 0.052 Uiso 1 1 calc R U . . .
H12B H 0.8604(3) -0.0334(4) 0.4362(7) 0.052 Uiso 1 1 calc R U . . .
C13 C 0.81975(13) 0.1061(2) 0.31943(14) 0.0366(5) Uani 1 1 d . . . . .
C14 C 0.79557(14) 0.2231(3) 0.37328(16) 0.0454(6) Uani 1 1 d . . . . .
C16 C 0.74417(15) 0.1140(3) 0.48550(18) 0.0483(6) Uani 1 1 d . . . . .
C19 C 0.96144(16) 0.4046(3) 0.33448(18) 0.0519(6) Uani 1 1 d . . . . .
H19 H 0.9068(15) 0.4582(15) 0.3104(7) 0.062 Uiso 1 1 calc R U . . .
C20 C 1.04585(16) 0.4788(3) 0.38769(19) 0.0557(7) Uani 1 1 d . . . . .
H20 H 1.04728(16) 0.582(3) 0.3990(4) 0.067 Uiso 1 1 calc R U . . .
C15 C 0.71444(15) 0.1592(3) 0.38627(16) 0.0443(5) Uani 1 1 d . . . . .
H15 H 0.6656(12) 0.2337(18) 0.3671(5) 0.053 Uiso 1 1 calc R U . . .
C22 C 1.12764(16) 0.2473(3) 0.40592(17) 0.0493(6) Uani 1 1 d . . . . .
H22 H 1.1862(15) 0.1925(14) 0.4304(6) 0.059 Uiso 1 1 calc R U . . .
C23 C 1.04219(14) 0.1751(3) 0.35243(16) 0.0456(6) Uani 1 1 d . . . . .
H23 H 1.04166(15) 0.072(3) 0.3401(4) 0.055 Uiso 1 1 calc R U . . .
C21 C 1.12672(15) 0.3970(3) 0.42298(16) 0.0496(6) 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C15 N1 C1 113.98(17) . . ?
C15 N1 C8 108.12(16) . . ?
C1 N1 C8 115.34(16) . . ?
N1 C1 C2 112.53(17) . . ?
N1 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
N1 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
C3 C2 C7 118.2(2) . . ?
C3 C2 C1 120.73(18) . . ?
C7 C2 C1 121.0(2) . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 Cl1 119.61(16) . . ?
C4 C5 Cl1 119.04(18) . . ?
C5 C6 C7 118.7(2) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C6 C7 C2 121.5(2) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
N1 C8 C9 112.19(18) . . ?
N1 C8 C13 102.87(16) . . ?
C9 C8 C13 113.72(17) . . ?
N1 C8 H8 109.3 . . ?
C9 C8 H8 109.3 . . ?
C13 C8 H8 109.3 . . ?
C18 C17 C13 115.78(17) . . ?
C18 C17 H17A 108.3 . . ?
C13 C17 H17A 108.3 . . ?
C18 C17 H17B 108.3 . . ?
C13 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
C19 C18 C23 117.4(2) . . ?
C19 C18 C17 120.64(19) . . ?
C23 C18 C17 121.9(2) . . ?
C10 C9 C8 113.1(2) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C11 111.1(2) . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 C12 111.00(19) . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C13 113.24(19) . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C12 108.62(17) . . ?
C14 C13 C8 99.53(15) . . ?
C12 C13 C8 110.30(18) . . ?
C14 C13 C17 113.38(18) . . ?
C12 C13 C17 112.39(16) . . ?
C8 C13 C17 111.89(16) . . ?
F2 C14 F1 105.37(19) . . ?
F2 C14 C13 113.44(17) . . ?
F1 C14 C13 111.10(18) . . ?
F2 C14 C15 112.61(19) . . ?
F1 C14 C15 107.20(16) . . ?
C13 C14 C15 107.02(18) . . ?
N2 C16 C15 178.7(3) . . ?
C18 C19 C20 122.0(2) . . ?
C18 C19 H19 119.0 . . ?
C20 C19 H19 119.0 . . ?
C21 C20 C19 118.2(2) . . ?
C21 C20 H20 120.9 . . ?
C19 C20 H20 120.9 . . ?
N1 C15 C16 112.01(19) . . ?
N1 C15 C14 104.61(17) . . ?
C16 C15 C14 112.61(19) . . ?
N1 C15 H15 109.2 . . ?
C16 C15 H15 109.2 . . ?
C14 C15 H15 109.2 . . ?
C21 C22 C23 118.2(2) . . ?
C21 C22 H22 120.9 . . ?
C23 C22 H22 120.9 . . ?
C22 C23 C18 121.5(2) . . ?
C22 C23 H23 119.2 . . ?
C18 C23 H23 119.2 . . ?
C22 C21 C20 122.6(2) . . ?
C22 C21 F3 117.9(2) . . ?
C20 C21 F3 119.5(2) . . ?
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
F1 C14 1.373(3) . ?
N1 C15 1.458(3) . ?
N1 C1 1.466(2) . ?
N1 C8 1.489(2) . ?
C1 C2 1.515(3) . ?
C1 H1A 1.002(16) . ?
C1 H1B 1.002(16) . ?
Cl1 C5 1.747(2) . ?
F2 C14 1.360(2) . ?
N2 C16 1.139(3) . ?
C2 C3 1.385(3) . ?
C2 C7 1.387(3) . ?
F3 C21 1.371(3) . ?
C3 C4 1.381(3) . ?
C3 H3 1.00(2) . ?
C4 C5 1.382(3) . ?
C4 H4 0.96(2) . ?
C5 C6 1.370(3) . ?
C6 C7 1.386(3) . ?
C6 H6 0.94(2) . ?
C7 H7 0.93(2) . ?
C8 C9 1.518(3) . ?
C8 C13 1.541(3) . ?
C8 H8 0.95(2) . ?
C17 C18 1.513(3) . ?
C17 C13 1.553(3) . ?
C17 H17A 0.958(15) . ?
C17 H17B 0.958(15) . ?
C18 C19 1.376(3) . ?
C18 C23 1.390(3) . ?
C9 C10 1.518(4) . ?
C9 H9A 0.978(15) . ?
C9 H9B 0.978(15) . ?
C10 C11 1.520(4) . ?
C10 H10A 0.964(18) . ?
C10 H10B 0.964(18) . ?
C11 C12 1.523(3) . ?
C11 H11A 1.010(18) . ?
C11 H11B 1.010(18) . ?
C12 C13 1.532(3) . ?
C12 H12A 0.985(15) . ?
C12 H12B 0.985(15) . ?
C13 C14 1.516(3) . ?
C14 C15 1.532(3) . ?
C16 C15 1.480(3) . ?
C19 C20 1.385(3) . ?
C19 H19 0.91(2) . ?
C20 C21 1.362(3) . ?
C20 H20 0.93(3) . ?
C15 H15 0.96(2) . ?
C22 C21 1.359(3) . ?
C22 C23 1.389(3) . ?
C22 H22 0.97(2) . ?
C23 H23 0.94(2) . ?
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
C15 N1 C1 C2 -80.8(2) . . . . ?
C8 N1 C1 C2 153.24(19) . . . . ?
N1 C1 C2 C3 -38.5(3) . . . . ?
N1 C1 C2 C7 144.2(2) . . . . ?
C7 C2 C3 C4 -0.1(3) . . . . ?
C1 C2 C3 C4 -177.5(2) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C3 C4 C5 Cl1 179.26(17) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
Cl1 C5 C6 C7 -179.24(18) . . . . ?
C5 C6 C7 C2 0.0(3) . . . . ?
C3 C2 C7 C6 0.1(3) . . . . ?
C1 C2 C7 C6 177.5(2) . . . . ?
C15 N1 C8 C9 157.93(18) . . . . ?
C1 N1 C8 C9 -73.2(2) . . . . ?
C15 N1 C8 C13 35.3(2) . . . . ?
C1 N1 C8 C13 164.25(18) . . . . ?
C13 C17 C18 C19 -91.9(3) . . . . ?
C13 C17 C18 C23 88.2(3) . . . . ?
N1 C8 C9 C10 -65.4(2) . . . . ?
C13 C8 C9 C10 50.8(2) . . . . ?
C8 C9 C10 C11 -53.4(3) . . . . ?
C9 C10 C11 C12 55.6(3) . . . . ?
C10 C11 C12 C13 -56.4(3) . . . . ?
C11 C12 C13 C14 160.23(18) . . . . ?
C11 C12 C13 C8 52.1(2) . . . . ?
C11 C12 C13 C17 -73.5(2) . . . . ?
N1 C8 C13 C14 -41.5(2) . . . . ?
C9 C8 C13 C14 -163.06(19) . . . . ?
N1 C8 C13 C12 72.5(2) . . . . ?
C9 C8 C13 C12 -49.0(2) . . . . ?
N1 C8 C13 C17 -161.56(17) . . . . ?
C9 C8 C13 C17 76.9(2) . . . . ?
C18 C17 C13 C14 63.3(2) . . . . ?
C18 C17 C13 C12 -60.4(3) . . . . ?
C18 C17 C13 C8 174.88(18) . . . . ?
C12 C13 C14 F2 43.6(2) . . . . ?
C8 C13 C14 F2 158.89(18) . . . . ?
C17 C13 C14 F2 -82.1(2) . . . . ?
C12 C13 C14 F1 162.05(16) . . . . ?
C8 C13 C14 F1 -82.63(19) . . . . ?
C17 C13 C14 F1 36.3(2) . . . . ?
C12 C13 C14 C15 -81.2(2) . . . . ?
C8 C13 C14 C15 34.1(2) . . . . ?
C17 C13 C14 C15 153.06(18) . . . . ?
C23 C18 C19 C20 -1.6(3) . . . . ?
C17 C18 C19 C20 178.5(2) . . . . ?
C18 C19 C20 C21 0.0(4) . . . . ?
C1 N1 C15 C16 94.5(2) . . . . ?
C8 N1 C15 C16 -135.78(18) . . . . ?
C1 N1 C15 C14 -143.19(18) . . . . ?
C8 N1 C15 C14 -13.5(2) . . . . ?
F2 C14 C15 N1 -139.23(18) . . . . ?
F1 C14 C15 N1 105.35(19) . . . . ?
C13 C14 C15 N1 -13.9(2) . . . . ?
F2 C14 C15 C16 -17.4(3) . . . . ?
F1 C14 C15 C16 -132.8(2) . . . . ?
C13 C14 C15 C16 108.0(2) . . . . ?
C21 C22 C23 C18 0.1(3) . . . . ?
C19 C18 C23 C22 1.6(3) . . . . ?
C17 C18 C23 C22 -178.53(19) . . . . ?
C23 C22 C21 C20 -1.8(4) . . . . ?
C23 C22 C21 F3 179.93(18) . . . . ?
C19 C20 C21 C22 1.7(4) . . . . ?
C19 C20 C21 F3 -180.0(2) . . . . ?
