#------------------------------------------------------------------------------
#$Date: 2021-04-05 17:15:40 +0200 (Mon 05 de Apr de 2021) $
#$Revision: 263829 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/78/7157860.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_7157860
loop_
_publ_author_name
'Samikannu, Ramesh'
'Sethuraman, Sankaranarayanan'
'Akula, Nagaraja'
'Radhakrishnan, Vignesh'
'Kamisetti, Srinivasarao'
'Banu, Shabana'
'Vetrichelvan, Muthalagu'
'Gupta, Anuradha'
'Li, Jianqing'
'Rampulla, Richard'
'Mathur, Arvind'
_publ_section_title
;
 Solvent-specific, DAST-mediated intramolecular Friedel-Crafts reaction:
 access to dibenzoxepine-fused spirooxindoles.
;
_journal_issue                   8
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1760
_journal_page_last               1768
_journal_paper_doi               10.1039/d0ob02461a
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C23 H15 Cl F3 N O3'
_chemical_formula_sum            'C23 H15 Cl F3 N O3'
_chemical_formula_weight         445.81
_chemical_name_common            Compound-3f
_chemical_name_systematic
2-Chloro-8-methoxy-6'-(trifluoromethyl)-6H-spiro[dibenzo[b,e]oxepine-11,3'-indolin]-2'-one
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-07-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_audit_update_record
;
2020-07-15 deposited with the CCDC.	2021-01-28 downloaded from the CCDC.
;
_cell_angle_alpha                111.955(2)
_cell_angle_beta                 97.653(2)
_cell_angle_gamma                98.734(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8400(4)
_cell_length_b                   11.8374(6)
_cell_length_c                   11.9176(6)
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      65.19
_cell_measurement_theta_min      4.09
_cell_volume                     991.91(9)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'Bruker APEX II area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28674
_diffrn_reflns_theta_full        65.19
_diffrn_reflns_theta_max         65.19
_diffrn_reflns_theta_min         4.09
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    2.197
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.4460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1491 before and 0.0633 after correction. The Ratio of minimum to maximum transmission is 0.5926. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_recrystallization_method
'obtained from clear solution of methanol by solvent evaporation at RT'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         3296
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0437
_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)+(0.0686P)²+0.3161P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1233
_reflns_number_gt                3146
_reflns_number_total             3296
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0ob02461a2.cif
_cod_data_source_block           Compound-3f
_cod_depositor_comments          'Adding full bibliography for 7157860.cif.'
_cod_database_code               7157860
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: F1B(0.5) F2B(0.5) F3B(0.5) F1A(0.5) F2A(0.5) F3A(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C7(H7), C12(H12), C14(H14), C15(H15), C19(H19),
 C20(H20), C22(H22)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_exptl_crystal_mounting_method
'mounted on nylon cryoloop with paratone oil'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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
Cl1 Cl 0.70679(9) 0.60496(6) 0.60758(6) 0.0769(2) Uani 1 1 d . . .
O1 O 0.2333(2) 0.05848(17) 1.08499(14) 0.0700(4) Uani 1 1 d . . .
O2 O 0.72202(19) 0.41187(13) 0.99341(12) 0.0574(4) Uani 1 1 d . . .
O3 O 0.61978(15) 0.11450(11) 0.66028(10) 0.0426(3) Uani 1 1 d . . .
N1 N 0.35652(18) 0.10569(13) 0.54482(12) 0.0393(3) Uani 1 1 d . . .
H1 H 0.3542 0.0398 0.4806 0.047 Uiso 1 1 calc R . .
C1 C 0.3536(3) 0.0746(2) 1.1926(2) 0.0653(6) Uani 1 1 d . . .
H1A H 0.4501 0.0363 1.1690 0.098 Uiso 1 1 calc R . .
H1B H 0.2946 0.0362 1.2391 0.098 Uiso 1 1 calc R . .
H1C H 0.3977 0.1621 1.2424 0.098 Uiso 1 1 calc R . .
C2 C 0.2912(3) 0.11123(18) 1.00908(17) 0.0481(4) Uani 1 1 d . . .
C3 C 0.1652(3) 0.10517(19) 0.91304(17) 0.0506(4) Uani 1 1 d . . .
H3 H 0.0488 0.0651 0.9020 0.061 Uiso 1 1 calc R . .
C4 C 0.2119(2) 0.15852(17) 0.83351(15) 0.0428(4) Uani 1 1 d . . .
H4 H 0.1252 0.1547 0.7700 0.051 Uiso 1 1 calc R . .
C5 C 0.3854(2) 0.21810(15) 0.84531(14) 0.0363(4) Uani 1 1 d . . .
C6 C 0.5116(2) 0.22107(16) 0.94157(15) 0.0411(4) Uani 1 1 d . . .
C7 C 0.4636(2) 0.16960(18) 1.02370(16) 0.0463(4) Uani 1 1 d . . .
H7 H 0.5485 0.1747 1.0888 0.056 Uiso 1 1 calc R . .
C8 C 0.4342(2) 0.26547(14) 0.74642(14) 0.0335(3) Uani 1 1 d . . .
C9 C 0.5773(2) 0.38643(15) 0.78581(15) 0.0361(4) Uani 1 1 d . . .
C10 C 0.7004(2) 0.44897(17) 0.89746(16) 0.0437(4) Uani 1 1 d . . .
C11 C 0.7002(2) 0.2809(2) 0.95966(18) 0.0524(5) Uani 1 1 d . . .
H11A H 0.7706 0.2660 1.0240 0.063 Uiso 1 1 calc R . .
H11B H 0.7416 0.2438 0.8838 0.063 Uiso 1 1 calc R . .
C12 C 0.5836(2) 0.43770(16) 0.69799(16) 0.0423(4) Uani 1 1 d . . .
H12 H 0.5065 0.3969 0.6215 0.051 Uiso 1 1 calc R . .
C13 C 0.7010(2) 0.54729(17) 0.72153(19) 0.0481(4) Uani 1 1 d . . .
C14 C 0.8166(3) 0.61039(18) 0.8338(2) 0.0529(5) Uani 1 1 d . . .
H14 H 0.8938 0.6853 0.8503 0.063 Uiso 1 1 calc R . .
C15 C 0.8158(2) 0.56105(18) 0.91998(18) 0.0530(5) Uani 1 1 d . . .
H15 H 0.8940 0.6029 0.9959 0.064 Uiso 1 1 calc R . .
C16 C 0.2671(2) 0.27410(14) 0.67129(14) 0.0334(3) Uani 1 1 d . . .
C17 C 0.2263(2) 0.17550(14) 0.55549(14) 0.0343(3) Uani 1 1 d . . .
C18 C 0.4867(2) 0.15385(14) 0.64735(14) 0.0339(3) Uani 1 1 d . . .
C19 C 0.1609(2) 0.35829(16) 0.70154(15) 0.0416(4) Uani 1 1 d . . .
H19 H 0.1879 0.4247 0.7787 0.050 Uiso 1 1 calc R . .
C20 C 0.0119(2) 0.34253(18) 0.61475(17) 0.0471(4) Uani 1 1 d . . .
H20 H -0.0612 0.3990 0.6336 0.057 Uiso 1 1 calc R . .
C21 C -0.0278(2) 0.24301(17) 0.50048(16) 0.0425(4) Uani 1 1 d . . .
C22 C 0.0785(2) 0.15747(16) 0.46860(15) 0.0398(4) Uani 1 1 d . . .
H22 H 0.0513 0.0906 0.3918 0.048 Uiso 1 1 calc R . .
C23 C -0.1881(3) 0.2275(2) 0.40744(19) 0.0574(5) Uani 1 1 d . . .
F1B F -0.1893(11) 0.3344(6) 0.3930(9) 0.132(3) Uani 0.50 1 d P . .
F2B F -0.3326(4) 0.2075(13) 0.4406(7) 0.128(2) Uani 0.50 1 d P . .
F3B F -0.1940(12) 0.1541(11) 0.2981(5) 0.153(5) Uani 0.50 1 d P . .
F1A F -0.1568(8) 0.2162(10) 0.3034(5) 0.109(3) Uani 0.50 1 d P . .
F2A F -0.2779(10) 0.3092(8) 0.4399(6) 0.121(3) Uani 0.50 1 d P . .
F3A F -0.2981(7) 0.1155(5) 0.3771(7) 0.0999(15) Uani 0.50 1 d P . .
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'
Cl Cl 0.3639 0.7018 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2 O1 C1 118.17(17) . . ?
C10 O2 C11 115.90(14) . . ?
C17 N1 H1 124.0 . . ?
C18 N1 H1 124.0 . . ?
C18 N1 C17 112.09(13) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 116.25(17) . . ?
O1 C2 C7 124.26(17) . . ?
C7 C2 C3 119.49(17) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.00(17) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.0 . . ?
C3 C4 C5 122.06(16) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 C6 117.07(15) . . ?
C4 C5 C8 119.98(14) . . ?
C6 C5 C8 122.66(14) . . ?
C5 C6 C11 120.63(16) . . ?
C7 C6 C5 120.83(16) . . ?
C7 C6 C11 118.54(15) . . ?
C2 C7 C6 120.52(16) . . ?
C2 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C5 C8 C9 119.60(13) . . ?
C5 C8 C18 105.35(12) . . ?
C9 C8 C18 110.16(12) . . ?
C16 C8 C5 109.55(12) . . ?
C16 C8 C9 109.79(13) . . ?
C16 C8 C18 100.66(11) . . ?
C10 C9 C8 127.90(15) . . ?
C12 C9 C8 115.37(14) . . ?
C12 C9 C10 116.73(15) . . ?
O2 C10 C9 126.19(16) . . ?
O2 C10 C15 113.47(16) . . ?
C9 C10 C15 120.33(17) . . ?
O2 C11 C6 110.86(16) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C9 C12 H12 119.1 . . ?
C13 C12 C9 121.80(17) . . ?
C13 C12 H12 119.1 . . ?
C12 C13 Cl1 119.88(15) . . ?
C14 C13 Cl1 119.37(15) . . ?
C14 C13 C12 120.74(18) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 C13 118.62(17) . . ?
C15 C14 H14 120.7 . . ?
C10 C15 H15 119.2 . . ?
C14 C15 C10 121.69(18) . . ?
C14 C15 H15 119.2 . . ?
C17 C16 C8 109.05(13) . . ?
C19 C16 C8 130.74(14) . . ?
C19 C16 C17 120.21(14) . . ?
C16 C17 N1 109.67(13) . . ?
C22 C17 N1 128.37(14) . . ?
C22 C17 C16 121.95(14) . . ?
O3 C18 N1 125.52(14) . . ?
O3 C18 C8 126.31(14) . . ?
N1 C18 C8 108.15(12) . . ?
C16 C19 H19 120.6 . . ?
C16 C19 C20 118.79(15) . . ?
C20 C19 H19 120.6 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.18(16) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C22 121.64(15) . . ?
C20 C21 C23 119.68(16) . . ?
C22 C21 C23 118.68(16) . . ?
C17 C22 C21 117.22(15) . . ?
C17 C22 H22 121.4 . . ?
C21 C22 H22 121.4 . . ?
F1B C23 C21 110.2(3) . . ?
F1B C23 F3A 139.2(3) . . ?
F2B C23 C21 114.2(2) . . ?
F2B C23 F1B 102.5(5) . . ?
F2B C23 F3A 52.6(4) . . ?
F3B C23 C21 115.8(3) . . ?
F3B C23 F1B 100.6(5) . . ?
F3B C23 F2B 111.7(5) . . ?
F3B C23 F1A 33.5(5) . . ?
F3B C23 F3A 68.5(5) . . ?
F1A C23 C21 113.8(3) . . ?
F1A C23 F1B 70.0(5) . . ?
F1A C23 F2B 130.8(4) . . ?
F1A C23 F3A 100.7(4) . . ?
F2A C23 C21 116.2(2) . . ?
F2A C23 F1B 46.3(4) . . ?
F2A C23 F2B 57.8(4) . . ?
F2A C23 F3B 125.7(4) . . ?
F2A C23 F1A 108.2(5) . . ?
F2A C23 F3A 106.9(5) . . ?
F3A C23 C21 109.8(2) . . ?
C23 F1B F1A 52.4(3) . . ?
F2A F1B C23 62.5(4) . . ?
F2A F1B F1A 106.6(6) . . ?
F2A F2B C23 60.7(3) . . ?
F3A F2B C23 67.7(4) . . ?
F3A F2B F2A 123.6(5) . . ?
C23 F3B F3A 58.9(4) . . ?
F1A F3B C23 73.3(7) . . ?
F1A F3B F3A 129.5(9) . . ?
C23 F1A F1B 57.6(4) . . ?
F3B F1A C23 73.2(7) . . ?
F3B F1A F1B 125.2(9) . . ?
F1B F2A C23 71.2(4) . . ?
F1B F2A F2B 129.9(7) . . ?
F2B F2A C23 61.5(3) . . ?
C23 F3A F3B 52.5(3) . . ?
F2B F3A C23 59.7(3) . . ?
F2B F3A F3B 104.0(4) . . ?
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
Cl1 C13 1.736(2) . ?
O1 C1 1.418(3) . ?
O1 C2 1.364(2) . ?
O2 C10 1.370(2) . ?
O2 C11 1.425(3) . ?
O3 C18 1.2198(19) . ?
N1 H1 0.8600 . ?
N1 C17 1.398(2) . ?
N1 C18 1.353(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.381(3) . ?
C2 C7 1.377(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.396(2) . ?
C5 C6 1.398(2) . ?
C5 C8 1.549(2) . ?
C6 C7 1.395(3) . ?
C6 C11 1.489(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.549(2) . ?
C8 C16 1.525(2) . ?
C8 C18 1.561(2) . ?
C9 C10 1.398(2) . ?
C9 C12 1.395(2) . ?
C10 C15 1.398(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12 0.9300 . ?
C12 C13 1.380(3) . ?
C13 C14 1.376(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.359(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.391(2) . ?
C16 C19 1.371(2) . ?
C17 C22 1.379(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.392(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.384(3) . ?
C21 C22 1.384(2) . ?
C21 C23 1.500(2) . ?
C22 H22 0.9300 . ?
C23 F1B 1.341(6) . ?
C23 F2B 1.266(4) . ?
C23 F3B 1.257(6) . ?
C23 F1A 1.258(5) . ?
C23 F2A 1.256(4) . ?
C23 F3A 1.357(4) . ?
F1B F1A 1.491(10) . ?
F1B F2A 1.025(8) . ?
F2B F2A 1.218(8) . ?
F2B F3A 1.165(8) . ?
F3B F1A 0.725(12) . ?
F3B F3A 1.474(10) . ?
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
Cl1 C13 C14 C15 -177.10(15) . . . . ?
O1 C2 C3 C4 178.63(18) . . . . ?
O1 C2 C7 C6 179.95(18) . . . . ?
O2 C10 C15 C14 178.15(17) . . . . ?
N1 C17 C22 C21 -177.71(16) . . . . ?
C1 O1 C2 C3 -173.1(2) . . . . ?
C1 O1 C2 C7 6.2(3) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C2 C7 C6 -0.8(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C3 C4 C5 C8 174.22(16) . . . . ?
C4 C5 C6 C7 -1.8(2) . . . . ?
C4 C5 C6 C11 179.02(16) . . . . ?
C4 C5 C8 C9 145.79(15) . . . . ?
C4 C5 C8 C16 17.85(19) . . . . ?
C4 C5 C8 C18 -89.67(17) . . . . ?
C5 C6 C7 C2 2.1(3) . . . . ?
C5 C6 C11 O2 65.7(2) . . . . ?
C5 C8 C9 C10 14.9(2) . . . . ?
C5 C8 C9 C12 -165.57(13) . . . . ?
C5 C8 C16 C17 -105.25(14) . . . . ?
C5 C8 C16 C19 73.9(2) . . . . ?
C5 C8 C18 O3 -70.78(19) . . . . ?
C5 C8 C18 N1 107.72(14) . . . . ?
C6 C5 C8 C9 -40.7(2) . . . . ?
C6 C5 C8 C16 -168.62(15) . . . . ?
C6 C5 C8 C18 83.86(17) . . . . ?
C7 C2 C3 C4 -0.7(3) . . . . ?
C7 C6 C11 O2 -113.50(18) . . . . ?
C8 C5 C6 C7 -175.52(15) . . . . ?
C8 C5 C6 C11 5.3(2) . . . . ?
C8 C9 C10 O2 2.5(3) . . . . ?
C8 C9 C10 C15 -177.04(16) . . . . ?
C8 C9 C12 C13 178.14(15) . . . . ?
C8 C16 C17 N1 -2.98(18) . . . . ?
C8 C16 C17 C22 178.21(15) . . . . ?
C8 C16 C19 C20 -178.66(17) . . . . ?
C9 C8 C16 C17 121.53(14) . . . . ?
C9 C8 C16 C19 -59.3(2) . . . . ?
C9 C8 C18 O3 59.5(2) . . . . ?
C9 C8 C18 N1 -122.01(14) . . . . ?
C9 C10 C15 C14 -2.2(3) . . . . ?
C9 C12 C13 Cl1 178.45(13) . . . . ?
C9 C12 C13 C14 -0.2(3) . . . . ?
C10 O2 C11 C6 -87.09(19) . . . . ?
C10 C9 C12 C13 -2.3(2) . . . . ?
C11 O2 C10 C9 37.2(2) . . . . ?
C11 O2 C10 C15 -143.18(17) . . . . ?
C11 C6 C7 C2 -178.75(18) . . . . ?
C12 C9 C10 O2 -176.98(16) . . . . ?
C12 C9 C10 C15 3.5(2) . . . . ?
C12 C13 C14 C15 1.6(3) . . . . ?
C13 C14 C15 C10 -0.4(3) . . . . ?
C16 C8 C9 C10 142.75(16) . . . . ?
C16 C8 C9 C12 -37.74(18) . . . . ?
C16 C8 C18 O3 175.35(16) . . . . ?
C16 C8 C18 N1 -6.15(16) . . . . ?
C16 C17 C22 C21 0.9(2) . . . . ?
C16 C19 C20 C21 0.3(3) . . . . ?
C17 N1 C18 O3 -176.55(15) . . . . ?
C17 N1 C18 C8 4.93(18) . . . . ?
C17 C16 C19 C20 0.4(3) . . . . ?
C18 N1 C17 C16 -1.33(19) . . . . ?
C18 N1 C17 C22 177.39(16) . . . . ?
C18 C8 C9 C10 -107.28(18) . . . . ?
C18 C8 C9 C12 72.23(17) . . . . ?
C18 C8 C16 C17 5.40(16) . . . . ?
C18 C8 C16 C19 -175.46(17) . . . . ?
C19 C16 C17 N1 177.78(15) . . . . ?
C19 C16 C17 C22 -1.0(2) . . . . ?
C19 C20 C21 C22 -0.5(3) . . . . ?
C19 C20 C21 C23 -179.63(18) . . . . ?
C20 C21 C22 C17 -0.1(3) . . . . ?
C20 C21 C23 F1B 51.0(6) . . . . ?
C20 C21 C23 F2B -63.8(8) . . . . ?
C20 C21 C23 F3B 164.2(8) . . . . ?
C20 C21 C23 F1A 127.3(6) . . . . ?
C20 C21 C23 F2A 0.7(8) . . . . ?
C20 C21 C23 F3A -120.7(5) . . . . ?
C21 C23 F1B F1A 108.8(4) . . . . ?
C21 C23 F1B F2A -107.4(4) . . . . ?
C21 C23 F2B F2A 106.7(3) . . . . ?
C21 C23 F2B F3A -97.1(3) . . . . ?
C21 C23 F3B F1A -94.6(10) . . . . ?
C21 C23 F3B F3A 102.3(3) . . . . ?
C21 C23 F1A F1B -103.9(4) . . . . ?
C21 C23 F1A F3B 101.3(9) . . . . ?
C21 C23 F2A F1B 93.6(5) . . . . ?
C21 C23 F2A F2B -103.4(3) . . . . ?
C21 C23 F3A F2B 105.9(3) . . . . ?
C21 C23 F3A F3B -110.8(4) . . . . ?
C22 C21 C23 F1B -128.2(6) . . . . ?
C22 C21 C23 F2B 117.1(7) . . . . ?
C22 C21 C23 F3B -14.9(8) . . . . ?
C22 C21 C23 F1A -51.9(6) . . . . ?
C22 C21 C23 F2A -178.4(7) . . . . ?
C22 C21 C23 F3A 60.1(5) . . . . ?
C23 C21 C22 C17 179.03(17) . . . . ?
C23 F1B F1A F3B 30.0(12) . . . . ?
C23 F1B F2A F2B -19.5(6) . . . . ?
C23 F2B F2A F1B 21.1(7) . . . . ?
C23 F2B F3A F3B -29.3(3) . . . . ?
C23 F3B F1A F1B -26.2(10) . . . . ?
C23 F3B F3A F2B 32.1(4) . . . . ?
F1B C23 F2B F2A -12.5(5) . . . . ?
F1B C23 F2B F3A 143.7(4) . . . . ?
F1B C23 F3B F1A 24.1(10) . . . . ?
F1B C23 F3B F3A -139.0(4) . . . . ?
F1B C23 F1A F3B -154.8(10) . . . . ?
F1B C23 F2A F2B 163.1(6) . . . . ?
F1B C23 F3A F2B -62.1(8) . . . . ?
F1B C23 F3A F3B 81.1(8) . . . . ?
F2B C23 F1B F1A -129.2(4) . . . . ?
F2B C23 F1B F2A 14.6(6) . . . . ?
F2B C23 F3B F1A 132.3(10) . . . . ?
F2B C23 F3B F3A -30.8(4) . . . . ?
F2B C23 F1A F1B 89.5(7) . . . . ?
F2B C23 F1A F3B -65.3(13) . . . . ?
F2B C23 F2A F1B -163.1(6) . . . . ?
F2B C23 F3A F3B 143.3(4) . . . . ?
F3B C23 F1B F1A -13.9(6) . . . . ?
F3B C23 F1B F2A 129.9(6) . . . . ?
F3B C23 F2B F2A -119.4(5) . . . . ?
F3B C23 F2B F3A 36.8(5) . . . . ?
F3B C23 F1A F1B 154.8(10) . . . . ?
F3B C23 F2A F1B -68.1(8) . . . . ?
F3B C23 F2A F2B 95.0(7) . . . . ?
F3B C23 F3A F2B -143.3(4) . . . . ?
F1A C23 F1B F2A 143.8(6) . . . . ?
F1A C23 F2B F2A -86.7(8) . . . . ?
F1A C23 F2B F3A 69.5(7) . . . . ?
F1A C23 F3B F3A -163.0(10) . . . . ?
F1A C23 F2A F1B -35.7(6) . . . . ?
F1A C23 F2A F2B 127.3(5) . . . . ?
F1A C23 F3A F2B -133.8(5) . . . . ?
F1A C23 F3A F3B 9.4(6) . . . . ?
F1A F1B F2A C23 29.2(4) . . . . ?
F1A F1B F2A F2B 9.7(9) . . . . ?
F1A F3B F3A C23 -21.3(13) . . . . ?
F1A F3B F3A F2B 10.9(15) . . . . ?
F2A C23 F1B F1A -143.8(6) . . . . ?
F2A C23 F2B F3A 156.2(4) . . . . ?
F2A C23 F3B F1A 67.1(12) . . . . ?
F2A C23 F3B F3A -95.9(7) . . . . ?
F2A C23 F1A F1B 26.7(4) . . . . ?
F2A C23 F1A F3B -128.0(10) . . . . ?
F2A C23 F3A F2B -20.9(4) . . . . ?
F2A C23 F3A F3B 122.4(5) . . . . ?
F2A F1B F1A C23 -33.1(5) . . . . ?
F2A F1B F1A F3B -3.2(15) . . . . ?
F2A F2B F3A C23 25.0(4) . . . . ?
F2A F2B F3A F3B -4.3(6) . . . . ?
F3A C23 F1B F1A -83.2(7) . . . . ?
F3A C23 F1B F2A 60.6(9) . . . . ?
F3A C23 F2B F2A -156.2(4) . . . . ?
F3A C23 F3B F1A 163.0(10) . . . . ?
F3A C23 F1A F1B 138.7(4) . . . . ?
F3A C23 F1A F3B -16.1(10) . . . . ?
F3A C23 F2A F1B -143.5(5) . . . . ?
F3A C23 F2A F2B 19.6(4) . . . . ?
F3A F2B F2A C23 -26.6(4) . . . . ?
F3A F2B F2A F1B -5.5(10) . . . . ?
F3A F3B F1A C23 18.9(11) . . . . ?
F3A F3B F1A F1B -7(2) . . . . ?
