#------------------------------------------------------------------------------
#$Date: 2021-11-06 22:41:47 +0200 (Sat, 06 Nov 2021) $
#$Revision: 270502 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158300.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_7158300
loop_
_publ_author_name
'Wang, Rui-Li'
'Jia, Shi-Kun'
'Guo, Ya-Jun'
'Yi, Yang'
'Hua, Yuan-Zhao'
'Lu, Hui-Jie'
'Wang, Min-Can'
_publ_section_title
;
 Dinuclear zinc-catalyzed enantioselective formal [3 + 2] cycloaddition of
 N-2,2,2-trifluoroethylisatin ketimines with low reactivity aurone
 derivatives.
;
_journal_issue                   39
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8492
_journal_page_last               8496
_journal_paper_doi               10.1039/d1ob01599k
_journal_volume                  19
_journal_year                    2021
_chemical_formula_sum            'C29 H24 Br F3 N2 O5'
_chemical_formula_weight         617.41
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-11-02 deposited with the CCDC.	2021-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                113.621(8)
_cell_angle_beta                 101.541(7)
_cell_angle_gamma                100.342(7)
_cell_formula_units_Z            1
_cell_length_a                   7.0824(5)
_cell_length_b                   9.9984(8)
_cell_length_c                   11.3089(9)
_cell_measurement_temperature    293(2)
_cell_volume                     688.15(11)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7450
_diffrn_reflns_point_group_measured_fraction_full 0.791
_diffrn_reflns_point_group_measured_fraction_max 0.791
_diffrn_reflns_theta_full        67.108
_diffrn_reflns_theta_max         67.108
_diffrn_reflns_theta_min         4.476
_exptl_absorpt_coefficient_mu    2.584
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_F_000             314
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 995 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(16)
_refine_ls_extinction_coef       0.0043(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         3900
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0487
_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)+(0.0643P)²+0.0394P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1303
_reflns_Friedel_coverage         0.583
_reflns_Friedel_fraction_full    0.583
_reflns_Friedel_fraction_max     0.583
_reflns_number_gt                3281
_reflns_number_total             3900
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob01599k2.cif
_cod_data_source_block           202008157
_cod_depositor_comments          'Adding full bibliography for 7158300.cif.'
_cod_original_cell_volume        688.15(10)
_cod_database_code               7158300
_shelx_shelxl_version_number     2014/7
_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   0.683
_shelx_estimated_absorpt_t_max   0.782
loop_
_space_group_symop_operation_xyz
'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_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
Br1 Br -0.07891(12) -0.20914(10) 0.79519(10) 0.0991(5) Uani 1 1 d . . . . .
C1 C 0.7002(10) 0.1872(9) 0.3926(7) 0.0476(15) Uani 1 1 d . . . . .
C2 C 0.5050(8) 0.2328(7) 0.4115(6) 0.0376(12) Uani 1 1 d . . . . .
C3 C 0.5485(10) 0.3868(7) 0.4108(7) 0.0433(14) Uani 1 1 d . . . . .
C4 C 0.7355(11) 0.4199(9) 0.3949(8) 0.0568(18) Uani 1 1 d . . . . .
C5 C 0.8110(15) 0.5489(10) 0.3803(10) 0.076(2) Uani 1 1 d . . . . .
H5 H 0.9389 0.5716 0.3712 0.091 Uiso 1 1 calc R U . . .
C6 C 0.6885(17) 0.6422(9) 0.3798(10) 0.084(3) Uani 1 1 d . . . . .
H6 H 0.7336 0.7279 0.3679 0.101 Uiso 1 1 calc R U . . .
C7 C 0.5019(14) 0.6106(9) 0.3964(9) 0.068(2) Uani 1 1 d . . . . .
H7 H 0.4228 0.6754 0.3965 0.082 Uiso 1 1 calc R U . . .
C8 C 0.4300(12) 0.4830(8) 0.4130(8) 0.0546(17) Uani 1 1 d . . . . .
H8 H 0.3041 0.4624 0.4255 0.065 Uiso 1 1 calc R U . . .
C9 C 0.4572(8) 0.2262(7) 0.5372(6) 0.0361(12) Uani 1 1 d . . . . .
C10 C 0.6339(9) 0.3063(7) 0.6704(7) 0.0444(14) Uani 1 1 d . . . . .
C11 C 0.5689(10) 0.4216(7) 0.7645(7) 0.0459(14) Uani 1 1 d . . . . .
C12 C 0.3775(9) 0.4145(7) 0.6971(6) 0.0393(13) Uani 1 1 d . . . . .
C13 C 0.2701(11) 0.5099(8) 0.7595(8) 0.0539(17) Uani 1 1 d . . . . .
H13 H 0.1413 0.5036 0.7143 0.065 Uiso 1 1 calc R U . . .
C14 C 0.3661(15) 0.6144(10) 0.8922(9) 0.070(2) Uani 1 1 d . . . . .
H14 H 0.2993 0.6811 0.9373 0.085 Uiso 1 1 calc R U . . .
C15 C 0.5559(16) 0.6256(11) 0.9619(9) 0.076(3) Uani 1 1 d . . . . .
H15 H 0.6135 0.6984 1.0518 0.092 Uiso 1 1 calc R U . . .
C16 C 0.6620(13) 0.5292(10) 0.8994(8) 0.064(2) Uani 1 1 d . . . . .
H16 H 0.7905 0.5361 0.9456 0.077 Uiso 1 1 calc R U . . .
C17 C 0.3613(9) 0.0552(7) 0.4834(6) 0.0384(13) Uani 1 1 d . . . . .
H17 H 0.4674 0.0051 0.4694 0.046 Uiso 1 1 calc R U . . .
C18 C 0.2235(9) 0.0168(7) 0.3415(6) 0.0388(13) Uani 1 1 d . . . . .
H18 H 0.0965 0.0397 0.3499 0.047 Uiso 1 1 calc R U . . .
C19 C 0.1796(11) -0.1479(8) 0.2398(7) 0.0524(16) Uani 1 1 d . . . . .
C20 C 0.2602(9) 0.0050(7) 0.5702(6) 0.0373(12) Uani 1 1 d . . . . .
C21 C 0.3406(11) -0.0839(8) 0.6232(7) 0.0495(16) Uani 1 1 d . . . . .
H21 H 0.4611 -0.1028 0.6116 0.059 Uiso 1 1 calc R U . . .
C22 C 0.2428(12) -0.1443(9) 0.6931(8) 0.0577(18) Uani 1 1 d . . . . .
H22 H 0.2960 -0.2045 0.7274 0.069 Uiso 1 1 calc R U . . .
C23 C 0.0662(12) -0.1140(8) 0.7111(7) 0.0557(18) Uani 1 1 d . . . . .
C24 C -0.0139(11) -0.0229(9) 0.6649(8) 0.0531(17) Uani 1 1 d . . . . .
H24 H -0.1316 -0.0013 0.6803 0.064 Uiso 1 1 calc R U . . .
C25 C 0.0844(9) 0.0363(8) 0.5946(7) 0.0444(14) Uani 1 1 d . . . . .
H25 H 0.0316 0.0986 0.5629 0.053 Uiso 1 1 calc R U . . .
F1 F 0.3409(8) -0.1927(5) 0.2218(5) 0.0745(13) Uani 1 1 d . . . . .
F2 F 0.0753(9) -0.2438(5) 0.2738(5) 0.0847(16) Uani 1 1 d . . . . .
F3 F 0.0698(8) -0.1728(5) 0.1177(5) 0.0803(14) Uani 1 1 d . . . . .
N1 N 0.8256(10) 0.3058(8) 0.3923(8) 0.0628(17) Uani 1 1 d D . . . .
H1 H 0.924(7) 0.287(7) 0.361(6) 0.042(18) Uiso 1 1 d D . . . .
N2 N 0.3331(7) 0.1182(6) 0.2984(5) 0.0385(11) Uani 1 1 d D . . . .
H2 H 0.262(8) 0.162(7) 0.264(6) 0.036(16) Uiso 1 1 d D . . . .
O1 O 0.7303(7) 0.0662(6) 0.3732(5) 0.0592(13) Uani 1 1 d . . . . .
O2 O 0.7882(7) 0.2701(6) 0.6831(5) 0.0612(13) Uani 1 1 d . . . . .
O3 O 0.3054(6) 0.3053(5) 0.5652(4) 0.0397(9) Uani 1 1 d . . . . .
C26 C 0.894(2) 0.1842(18) 0.0741(16) 0.133(5) Uani 1 1 d D U . . .
C27 C 0.677(2) 0.073(2) 0.0164(18) 0.165(7) Uani 1 1 d D U . . .
H27A H 0.5809 0.1308 0.0235 0.248 Uiso 1 1 calc R U . . .
H27B H 0.6629 0.0167 0.0672 0.248 Uiso 1 1 calc R U . . .
H27C H 0.6523 0.0041 -0.0769 0.248 Uiso 1 1 calc R U . . .
C28 C 1.097(3) 0.344(3) 0.016(2) 0.178(9) Uani 1 1 d D . . . .
H28A H 1.1221 0.4211 0.1081 0.213 Uiso 1 1 calc R U . . .
H28B H 1.0820 0.3935 -0.0423 0.213 Uiso 1 1 calc R U . . .
C29 C 1.281(4) 0.283(3) 0.008(2) 0.216(11) Uani 1 1 d D . . . .
H29A H 1.3956 0.3550 0.0832 0.323 Uiso 1 1 calc R U . . .
H29B H 1.3087 0.2696 -0.0751 0.323 Uiso 1 1 calc R U . . .
H29C H 1.2535 0.1873 0.0111 0.323 Uiso 1 1 calc R U . . .
O4 O 1.0168(10) 0.2381(10) 0.1779(7) 0.090(2) Uani 1 1 d . . . . .
O5 O 0.902(2) 0.2236(16) -0.0241(10) 0.162(5) Uani 1 1 d 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'
Br Br -0.6763 1.2805 '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
O1 C1 N1 125.9(6) . . ?
O1 C1 C2 127.1(6) . . ?
N1 C1 C2 106.8(6) . . ?
N2 C2 C3 113.0(5) . . ?
N2 C2 C9 103.7(4) . . ?
C3 C2 C9 117.5(5) . . ?
N2 C2 C1 108.8(5) . . ?
C3 C2 C1 101.8(5) . . ?
C9 C2 C1 112.1(5) . . ?
C4 C3 C8 120.1(6) . . ?
C4 C3 C2 108.4(6) . . ?
C8 C3 C2 131.3(6) . . ?
C3 C4 C5 121.7(8) . . ?
C3 C4 N1 110.1(6) . . ?
C5 C4 N1 128.1(7) . . ?
C6 C5 C4 117.5(8) . . ?
C6 C5 H5 121.3 . . ?
C4 C5 H5 121.3 . . ?
C7 C6 C5 121.2(7) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 120.7(8) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C3 C8 C7 118.8(7) . . ?
C3 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
O3 C9 C17 109.0(4) . . ?
O3 C9 C10 105.2(5) . . ?
C17 C9 C10 116.9(5) . . ?
O3 C9 C2 107.6(4) . . ?
C17 C9 C2 101.6(5) . . ?
C10 C9 C2 116.2(5) . . ?
O2 C10 C11 131.4(6) . . ?
O2 C10 C9 123.1(6) . . ?
C11 C10 C9 105.4(5) . . ?
C12 C11 C16 120.2(7) . . ?
C12 C11 C10 107.6(6) . . ?
C16 C11 C10 132.2(7) . . ?
O3 C12 C13 123.4(6) . . ?
O3 C12 C11 114.1(5) . . ?
C13 C12 C11 122.5(6) . . ?
C14 C13 C12 115.8(7) . . ?
C14 C13 H13 122.1 . . ?
C12 C13 H13 122.1 . . ?
C13 C14 C15 123.4(8) . . ?
C13 C14 H14 118.3 . . ?
C15 C14 H14 118.3 . . ?
C14 C15 C16 120.6(8) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 117.5(8) . . ?
C15 C16 H16 121.2 . . ?
C11 C16 H16 121.2 . . ?
C20 C17 C9 117.5(5) . . ?
C20 C17 C18 116.1(5) . . ?
C9 C17 C18 100.1(4) . . ?
C20 C17 H17 107.5 . . ?
C9 C17 H17 107.5 . . ?
C18 C17 H17 107.5 . . ?
N2 C18 C19 110.4(5) . . ?
N2 C18 C17 105.2(4) . . ?
C19 C18 C17 112.8(5) . . ?
N2 C18 H18 109.4 . . ?
C19 C18 H18 109.4 . . ?
C17 C18 H18 109.4 . . ?
F1 C19 F2 105.9(6) . . ?
F1 C19 F3 106.1(6) . . ?
F2 C19 F3 107.0(6) . . ?
F1 C19 C18 114.8(6) . . ?
F2 C19 C18 112.2(6) . . ?
F3 C19 C18 110.3(6) . . ?
C25 C20 C21 118.0(6) . . ?
C25 C20 C17 123.2(5) . . ?
C21 C20 C17 118.7(6) . . ?
C22 C21 C20 120.7(7) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 119.1(6) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C24 C23 C22 122.0(6) . . ?
C24 C23 Br1 118.8(6) . . ?
C22 C23 Br1 119.2(5) . . ?
C23 C24 C25 118.4(6) . . ?
C23 C24 H24 120.8 . . ?
C25 C24 H24 120.8 . . ?
C24 C25 C20 121.7(6) . . ?
C24 C25 H25 119.2 . . ?
C20 C25 H25 119.2 . . ?
C1 N1 C4 112.5(6) . . ?
C1 N1 H1 116(5) . . ?
C4 N1 H1 127(5) . . ?
C2 N2 C18 109.9(4) . . ?
C2 N2 H2 110(4) . . ?
C18 N2 H2 115(4) . . ?
C12 O3 C9 107.6(4) . . ?
O4 C26 O5 124.5(16) . . ?
O4 C26 C27 133.5(16) . . ?
O5 C26 C27 101.5(15) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O5 C28 C29 114.2(18) . . ?
O5 C28 H28A 108.7 . . ?
C29 C28 H28A 108.7 . . ?
O5 C28 H28B 108.7 . . ?
C29 C28 H28B 108.7 . . ?
H28A C28 H28B 107.6 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C26 O5 C28 110.8(13) . . ?
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
Br1 C23 1.905(7) . ?
C1 O1 1.207(8) . ?
C1 N1 1.349(9) . ?
C1 C2 1.559(8) . ?
C2 N2 1.460(8) . ?
C2 C3 1.519(8) . ?
C2 C9 1.549(8) . ?
C3 C4 1.372(10) . ?
C3 C8 1.381(10) . ?
C4 C5 1.392(11) . ?
C4 N1 1.397(11) . ?
C5 C6 1.384(14) . ?
C5 H5 0.9300 . ?
C6 C7 1.371(13) . ?
C6 H6 0.9300 . ?
C7 C8 1.386(10) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 O3 1.457(7) . ?
C9 C17 1.529(8) . ?
C9 C10 1.548(8) . ?
C10 O2 1.212(8) . ?
C10 C11 1.440(10) . ?
C11 C12 1.390(9) . ?
C11 C16 1.395(10) . ?
C12 O3 1.367(7) . ?
C12 C13 1.386(9) . ?
C13 C14 1.374(11) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(14) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(13) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C20 1.508(8) . ?
C17 C18 1.556(8) . ?
C17 H17 0.9800 . ?
C18 N2 1.460(7) . ?
C18 C19 1.512(9) . ?
C18 H18 0.9800 . ?
C19 F1 1.323(9) . ?
C19 F2 1.330(8) . ?
C19 F3 1.341(8) . ?
C20 C25 1.390(9) . ?
C20 C21 1.395(9) . ?
C21 C22 1.386(10) . ?
C21 H21 0.9300 . ?
C22 C23 1.373(11) . ?
C22 H22 0.9300 . ?
C23 C24 1.369(10) . ?
C24 C25 1.385(9) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
N1 H1 0.86(3) . ?
N2 H2 0.85(3) . ?
C26 O4 1.159(16) . ?
C26 O5 1.327(16) . ?
C26 C27 1.557(18) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 O5 1.508(17) . ?
C28 C29 1.54(2) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O4 0.86(3) 2.19(5) 2.916(9) 142(6) .
N2 H2 O4 0.85(3) 2.23(3) 3.060(8) 166(6) 1_455
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
O1 C1 C2 N2 -52.5(8) . . . . ?
N1 C1 C2 N2 123.2(6) . . . . ?
O1 C1 C2 C3 -172.0(7) . . . . ?
N1 C1 C2 C3 3.7(7) . . . . ?
O1 C1 C2 C9 61.6(9) . . . . ?
N1 C1 C2 C9 -122.7(6) . . . . ?
N2 C2 C3 C4 -116.7(6) . . . . ?
C9 C2 C3 C4 122.5(6) . . . . ?
C1 C2 C3 C4 -0.2(7) . . . . ?
N2 C2 C3 C8 57.9(10) . . . . ?
C9 C2 C3 C8 -62.9(9) . . . . ?
C1 C2 C3 C8 174.4(7) . . . . ?
C8 C3 C4 C5 -0.2(12) . . . . ?
C2 C3 C4 C5 175.1(8) . . . . ?
C8 C3 C4 N1 -178.6(7) . . . . ?
C2 C3 C4 N1 -3.2(9) . . . . ?
C3 C4 C5 C6 -1.2(14) . . . . ?
N1 C4 C5 C6 176.8(9) . . . . ?
C4 C5 C6 C7 1.6(15) . . . . ?
C5 C6 C7 C8 -0.6(15) . . . . ?
C4 C3 C8 C7 1.2(11) . . . . ?
C2 C3 C8 C7 -172.9(7) . . . . ?
C6 C7 C8 C3 -0.9(12) . . . . ?
N2 C2 C9 O3 -76.6(5) . . . . ?
C3 C2 C9 O3 48.8(7) . . . . ?
C1 C2 C9 O3 166.2(5) . . . . ?
N2 C2 C9 C17 37.8(5) . . . . ?
C3 C2 C9 C17 163.3(5) . . . . ?
C1 C2 C9 C17 -79.4(6) . . . . ?
N2 C2 C9 C10 165.8(5) . . . . ?
C3 C2 C9 C10 -68.7(7) . . . . ?
C1 C2 C9 C10 48.6(7) . . . . ?
O3 C9 C10 O2 -179.4(6) . . . . ?
C17 C9 C10 O2 59.6(8) . . . . ?
C2 C9 C10 O2 -60.5(8) . . . . ?
O3 C9 C10 C11 1.2(6) . . . . ?
C17 C9 C10 C11 -119.8(6) . . . . ?
C2 C9 C10 C11 120.1(6) . . . . ?
O2 C10 C11 C12 -180.0(7) . . . . ?
C9 C10 C11 C12 -0.6(7) . . . . ?
O2 C10 C11 C16 0.7(13) . . . . ?
C9 C10 C11 C16 -180.0(7) . . . . ?
C16 C11 C12 O3 179.2(6) . . . . ?
C10 C11 C12 O3 -0.3(7) . . . . ?
C16 C11 C12 C13 -1.1(10) . . . . ?
C10 C11 C12 C13 179.5(6) . . . . ?
O3 C12 C13 C14 -179.3(6) . . . . ?
C11 C12 C13 C14 1.0(10) . . . . ?
C12 C13 C14 C15 -0.5(12) . . . . ?
C13 C14 C15 C16 0.1(15) . . . . ?
C14 C15 C16 C11 -0.2(14) . . . . ?
C12 C11 C16 C15 0.6(11) . . . . ?
C10 C11 C16 C15 179.9(8) . . . . ?
O3 C9 C17 C20 -56.1(6) . . . . ?
C10 C9 C17 C20 62.9(7) . . . . ?
C2 C9 C17 C20 -169.5(5) . . . . ?
O3 C9 C17 C18 70.5(5) . . . . ?
C10 C9 C17 C18 -170.5(5) . . . . ?
C2 C9 C17 C18 -43.0(5) . . . . ?
C20 C17 C18 N2 161.2(5) . . . . ?
C9 C17 C18 N2 33.7(6) . . . . ?
C20 C17 C18 C19 -78.4(7) . . . . ?
C9 C17 C18 C19 154.1(5) . . . . ?
N2 C18 C19 F1 60.6(7) . . . . ?
C17 C18 C19 F1 -56.9(7) . . . . ?
N2 C18 C19 F2 -178.4(6) . . . . ?
C17 C18 C19 F2 64.2(8) . . . . ?
N2 C18 C19 F3 -59.2(7) . . . . ?
C17 C18 C19 F3 -176.6(6) . . . . ?
C9 C17 C20 C25 68.2(8) . . . . ?
C18 C17 C20 C25 -50.2(8) . . . . ?
C9 C17 C20 C21 -115.2(6) . . . . ?
C18 C17 C20 C21 126.4(6) . . . . ?
C25 C20 C21 C22 2.7(10) . . . . ?
C17 C20 C21 C22 -174.1(7) . . . . ?
C20 C21 C22 C23 -0.8(12) . . . . ?
C21 C22 C23 C24 -1.6(12) . . . . ?
C21 C22 C23 Br1 175.3(6) . . . . ?
C22 C23 C24 C25 1.9(12) . . . . ?
Br1 C23 C24 C25 -175.1(6) . . . . ?
C23 C24 C25 C20 0.2(11) . . . . ?
C21 C20 C25 C24 -2.4(10) . . . . ?
C17 C20 C25 C24 174.2(6) . . . . ?
O1 C1 N1 C4 169.8(7) . . . . ?
C2 C1 N1 C4 -6.0(9) . . . . ?
C3 C4 N1 C1 6.1(10) . . . . ?
C5 C4 N1 C1 -172.1(8) . . . . ?
C3 C2 N2 C18 -145.1(5) . . . . ?
C9 C2 N2 C18 -16.8(6) . . . . ?
C1 C2 N2 C18 102.7(5) . . . . ?
C19 C18 N2 C2 -132.6(5) . . . . ?
C17 C18 N2 C2 -10.7(6) . . . . ?
C13 C12 O3 C9 -178.6(6) . . . . ?
C11 C12 O3 C9 1.1(6) . . . . ?
C17 C9 O3 C12 124.7(5) . . . . ?
C10 C9 O3 C12 -1.4(6) . . . . ?
C2 C9 O3 C12 -125.9(5) . . . . ?
O4 C26 O5 C28 2(2) . . . . ?
C27 C26 O5 C28 174.8(15) . . . . ?
C29 C28 O5 C26 76(2) . . . . ?
