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#$Date: 2025-04-05 06:27:34 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298958 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/97/7249741.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_7249741
loop_
_publ_author_name
'Liang, Hanyu'
'Cao, Jiaxuan'
'Zhang, Hailong'
'Huang, Longjie'
'Liu, Siqi'
'Wu, Tianhao'
'Xiao, Xiao'
'Zhao, Baoguo'
_publ_section_title
;
 Direct asymmetric α-C--H functionalization of N-unprotected allylamine
 catalyzed by chiral pyridoxal
;
_journal_issue                   5
_journal_name_full               'Green Chemistry'
_journal_page_first              1374
_journal_page_last               1380
_journal_paper_doi               10.1039/D4GC05739B
_journal_volume                  27
_journal_year                    2025
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C24 H19 Br F3 N O2, C4 H8 O'
_chemical_formula_sum            'C28 H27 Br F3 N O3'
_chemical_formula_weight         562.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-13
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-19 deposited with the CCDC.	2025-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8722(4)
_cell_length_b                   15.5610(10)
_cell_length_c                   28.0723(18)
_cell_measurement_reflns_used    7113
_cell_measurement_temperature    170
_cell_measurement_theta_max      63.185
_cell_measurement_theta_min      3.148
_cell_volume                     2565.2(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0736
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            15090
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        63.595
_diffrn_reflns_theta_max         63.595
_diffrn_reflns_theta_min         3.148
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.637
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.5659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1292 before and 0.0815 after correction.
The Ratio of minimum to maximum transmission is 0.7521.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_description       needle
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 1156 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.034(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4137
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0324P)²+0.0224P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0883
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                3448
_reflns_number_total             4137
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4gc05739b2.cif
_cod_data_source_block           202418424_0m
_cod_depositor_comments
'Adding full bibliography for 7249740--7249741.cif.'
_cod_database_code               7249741
_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_max   0.949
_shelx_estimated_absorpt_t_min   0.760
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C14(H14), C12(H12), C2(H2A), C6(H6), C3(H3), C16(H16), C15(H15),
 C13(H13), C18(H18), C5(H5), C8(H8), C20(H20), C24(H24), C21(H21), C22(H22),
 C23(H23)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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 0.55548(13) 0.94474(4) 0.53387(2) 0.0454(2) Uani 1 1 d . . . . .
F2 F 0.3375(7) 0.29286(18) 0.68128(10) 0.0442(9) Uani 1 1 d . . . . .
F3 F 0.2452(7) 0.23583(19) 0.61498(11) 0.0484(10) Uani 1 1 d . . . . .
F1 F 0.5970(7) 0.26288(19) 0.62961(11) 0.0476(9) Uani 1 1 d . . . . .
O2 O 0.1505(7) 0.4139(2) 0.63045(12) 0.0324(9) Uani 1 1 d . . . . .
H2 H 0.098720 0.451787 0.612091 0.049 Uiso 1 1 calc R U . . .
O1 O 0.9075(7) 0.5375(2) 0.58726(11) 0.0328(9) Uani 1 1 d . . . . .
O3 O 0.2376(8) 0.6510(2) 0.66240(14) 0.0424(10) Uani 1 1 d . . . . .
N1 N 0.5373(9) 0.5268(2) 0.61077(12) 0.0267(10) Uani 1 1 d . . . . .
H1 H 0.402847 0.551752 0.610742 0.032 Uiso 1 1 calc R U . . .
C11 C 0.3597(10) 0.3756(3) 0.55814(17) 0.0257(13) Uani 1 1 d . . . . .
C10 C 0.3630(10) 0.3843(3) 0.61291(17) 0.0263(12) Uani 1 1 d . . . . .
C14 C 0.3416(11) 0.3545(3) 0.45924(19) 0.0334(14) Uani 1 1 d . . . . .
H14 H 0.335231 0.347116 0.425672 0.040 Uiso 1 1 calc R U . . .
C1 C 0.6702(10) 0.6596(3) 0.57699(16) 0.0260(12) Uani 1 1 d . . . . .
C17 C 0.3841(11) 0.2937(3) 0.63483(19) 0.0362(16) Uani 1 1 d . . . . .
C12 C 0.1633(9) 0.3451(3) 0.53586(19) 0.0294(12) Uani 1 1 d . . . . .
H12 H 0.032946 0.331673 0.554475 0.035 Uiso 1 1 calc R U . . .
C2 C 0.8430(10) 0.7197(3) 0.58270(17) 0.0307(13) Uani 1 1 d . . . . .
H2A H 0.986738 0.702196 0.594840 0.037 Uiso 1 1 calc R U . . .
C6 C 0.4621(11) 0.6841(3) 0.55722(16) 0.0287(13) Uani 1 1 d . . . . .
H6 H 0.345128 0.642713 0.552756 0.034 Uiso 1 1 calc R U . . .
C19 C 0.7956(11) 0.4483(4) 0.76082(18) 0.0343(13) Uani 1 1 d . . . . .
C9 C 0.5590(10) 0.4410(3) 0.63153(15) 0.0261(11) Uani 1 1 d . . . . .
H9 H 0.706115 0.415521 0.620479 0.031 Uiso 1 1 calc R U . . .
C7 C 0.7150(10) 0.5690(3) 0.59174(17) 0.0280(13) Uani 1 1 d . . . . .
C3 C 0.8069(11) 0.8049(3) 0.57079(17) 0.0316(14) Uani 1 1 d . . . . .
H3 H 0.922733 0.846585 0.575806 0.038 Uiso 1 1 calc R U . . .
C16 C 0.5475(10) 0.3957(3) 0.53006(16) 0.0270(11) Uani 1 1 d . . . . .
H16 H 0.683066 0.416221 0.544609 0.032 Uiso 1 1 calc R U . . .
C15 C 0.5383(11) 0.3860(3) 0.48071(17) 0.0332(13) Uani 1 1 d . . . . .
H15 H 0.666256 0.400922 0.461738 0.040 Uiso 1 1 calc R U . . .
C13 C 0.1562(11) 0.3341(3) 0.48711(18) 0.0328(14) Uani 1 1 d . . . . .
H13 H 0.021975 0.312299 0.472602 0.039 Uiso 1 1 calc R U . . .
C18 C 0.7524(10) 0.4323(3) 0.70988(16) 0.0307(13) Uani 1 1 d . . . . .
H18 H 0.872421 0.405316 0.692821 0.037 Uiso 1 1 calc R U . . .
C5 C 0.4261(11) 0.7694(3) 0.54403(16) 0.0295(12) Uani 1 1 d . . . . .
H5 H 0.285905 0.786985 0.530237 0.035 Uiso 1 1 calc R U . . .
C8 C 0.5692(11) 0.4506(3) 0.68506(16) 0.0301(12) Uani 1 1 d . . . . .
H8 H 0.437875 0.470617 0.701394 0.036 Uiso 1 1 calc R U . . .
C20 C 1.0029(11) 0.4241(4) 0.78081(17) 0.0395(16) Uani 1 1 d . . . . .
H20 H 1.113033 0.396046 0.761533 0.047 Uiso 1 1 calc R U . . .
C4 C 0.6011(11) 0.8282(3) 0.55162(17) 0.0320(14) Uani 1 1 d . . . . .
C24 C 0.6385(12) 0.4899(4) 0.79018(19) 0.0473(17) Uani 1 1 d . . . . .
H24 H 0.495442 0.507186 0.777601 0.057 Uiso 1 1 calc R U . . .
C21 C 1.0518(13) 0.4403(4) 0.82829(18) 0.0495(16) Uani 1 1 d . . . . .
H21 H 1.194095 0.422690 0.841099 0.059 Uiso 1 1 calc R U . . .
C22 C 0.8981(14) 0.4811(4) 0.8568(2) 0.054(2) Uani 1 1 d . . . . .
H22 H 0.933016 0.492170 0.889281 0.065 Uiso 1 1 calc R U . . .
C23 C 0.6901(14) 0.5062(4) 0.8380(2) 0.057(2) Uani 1 1 d . . . . .
H23 H 0.582123 0.534720 0.857607 0.068 Uiso 1 1 calc R U . . .
C28 C 0.3608(13) 0.7231(4) 0.6814(2) 0.057(2) Uani 1 1 d . . . . .
H28A H 0.288623 0.777869 0.671793 0.069 Uiso 1 1 calc R U . . .
H28B H 0.520662 0.722759 0.670218 0.069 Uiso 1 1 calc R U . . .
C25 C 0.0644(14) 0.6291(4) 0.6957(2) 0.0569(18) Uani 1 1 d . . . . .
H25A H 0.057976 0.566031 0.699951 0.068 Uiso 1 1 calc R U . . .
H25B H -0.085659 0.648971 0.683944 0.068 Uiso 1 1 calc R U . . .
C26 C 0.1190(18) 0.6717(5) 0.7420(2) 0.079(3) Uani 1 1 d . . . . .
H26A H 0.124857 0.629157 0.768184 0.094 Uiso 1 1 calc R U . . .
H26B H 0.004274 0.716100 0.749855 0.094 Uiso 1 1 calc R U . . .
C27 C 0.3501(17) 0.7118(5) 0.7339(3) 0.076(3) Uani 1 1 d . . . . .
H27A H 0.362604 0.767737 0.750442 0.091 Uiso 1 1 calc R U . . .
H27B H 0.473245 0.673404 0.745186 0.091 Uiso 1 1 calc R U . . .
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
C10 O2 H2 109.5 . . ?
C25 O3 C28 107.6(5) . . ?
C9 N1 H1 118.7 . . ?
C7 N1 H1 118.7 . . ?
C7 N1 C9 122.5(5) . . ?
C12 C11 C10 119.1(5) . . ?
C16 C11 C10 122.3(5) . . ?
C16 C11 C12 118.5(5) . . ?
O2 C10 C11 111.3(4) . . ?
O2 C10 C17 103.2(4) . . ?
O2 C10 C9 110.7(4) . . ?
C17 C10 C11 108.5(4) . . ?
C9 C10 C11 113.4(4) . . ?
C9 C10 C17 109.1(4) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.4(5) . . ?
C2 C1 C6 120.2(5) . . ?
C2 C1 C7 118.4(5) . . ?
C6 C1 C7 121.5(5) . . ?
F2 C17 F3 106.0(5) . . ?
F2 C17 F1 107.1(5) . . ?
F2 C17 C10 112.5(4) . . ?
F3 C17 F1 106.3(4) . . ?
F3 C17 C10 113.6(5) . . ?
F1 C17 C10 110.9(5) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(5) . . ?
C13 C12 H12 119.6 . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 C1 120.3(6) . . ?
C3 C2 H2A 119.8 . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.9(5) . . ?
C5 C6 H6 120.1 . . ?
C20 C19 C18 119.8(5) . . ?
C20 C19 C24 117.7(5) . . ?
C24 C19 C18 122.5(5) . . ?
N1 C9 C10 108.8(4) . . ?
N1 C9 H9 108.2 . . ?
N1 C9 C8 108.0(4) . . ?
C10 C9 H9 108.2 . . ?
C8 C9 C10 115.1(4) . . ?
C8 C9 H9 108.2 . . ?
O1 C7 N1 123.7(5) . . ?
O1 C7 C1 120.4(5) . . ?
N1 C7 C1 115.8(5) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.9(5) . . ?
C4 C3 H3 120.6 . . ?
C11 C16 H16 119.7 . . ?
C11 C16 C15 120.5(5) . . ?
C15 C16 H16 119.7 . . ?
C14 C15 C16 120.0(6) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C13 C12 120.7(5) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C19 C18 H18 115.9 . . ?
C8 C18 C19 128.3(5) . . ?
C8 C18 H18 115.9 . . ?
C6 C5 H5 120.9 . . ?
C4 C5 C6 118.2(6) . . ?
C4 C5 H5 120.9 . . ?
C9 C8 H8 118.7 . . ?
C18 C8 C9 122.6(5) . . ?
C18 C8 H8 118.7 . . ?
C19 C20 H20 119.3 . . ?
C21 C20 C19 121.3(6) . . ?
C21 C20 H20 119.3 . . ?
C3 C4 Br1 118.6(4) . . ?
C3 C4 C5 122.5(5) . . ?
C5 C4 Br1 118.9(4) . . ?
C19 C24 H24 119.8 . . ?
C19 C24 C23 120.5(7) . . ?
C23 C24 H24 119.8 . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.8(6) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 120.3 . . ?
C21 C22 C23 119.3(6) . . ?
C23 C22 H22 120.3 . . ?
C24 C23 H23 119.8 . . ?
C22 C23 C24 120.4(7) . . ?
C22 C23 H23 119.8 . . ?
O3 C28 H28A 110.8 . . ?
O3 C28 H28B 110.8 . . ?
O3 C28 C27 104.8(6) . . ?
H28A C28 H28B 108.9 . . ?
C27 C28 H28A 110.8 . . ?
C27 C28 H28B 110.8 . . ?
O3 C25 H25A 110.1 . . ?
O3 C25 H25B 110.1 . . ?
O3 C25 C26 108.2(6) . . ?
H25A C25 H25B 108.4 . . ?
C26 C25 H25A 110.1 . . ?
C26 C25 H25B 110.1 . . ?
C25 C26 H26A 110.9 . . ?
C25 C26 H26B 110.9 . . ?
C25 C26 C27 104.2(6) . . ?
H26A C26 H26B 108.9 . . ?
C27 C26 H26A 110.9 . . ?
C27 C26 H26B 110.9 . . ?
C28 C27 C26 103.7(6) . . ?
C28 C27 H27A 111.0 . . ?
C28 C27 H27B 111.0 . . ?
C26 C27 H27A 111.0 . . ?
C26 C27 H27B 111.0 . . ?
H27A C27 H27B 109.0 . . ?
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 C4 1.900(5) . ?
F2 C17 1.332(6) . ?
F3 C17 1.337(6) . ?
F1 C17 1.347(7) . ?
O2 H2 0.8400 . ?
O2 C10 1.418(6) . ?
O1 C7 1.239(6) . ?
O3 C28 1.438(7) . ?
O3 C25 1.422(8) . ?
N1 H1 0.8800 . ?
N1 C9 1.463(5) . ?
N1 C7 1.344(7) . ?
C11 C10 1.544(7) . ?
C11 C12 1.395(7) . ?
C11 C16 1.391(7) . ?
C10 C17 1.543(7) . ?
C10 C9 1.541(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(8) . ?
C14 C13 1.377(8) . ?
C1 C2 1.389(7) . ?
C1 C6 1.395(7) . ?
C1 C7 1.493(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(7) . ?
C2 H2A 0.9500 . ?
C2 C3 1.384(7) . ?
C6 H6 0.9500 . ?
C6 C5 1.395(6) . ?
C19 C18 1.473(7) . ?
C19 C20 1.392(8) . ?
C19 C24 1.396(8) . ?
C9 H9 1.0000 . ?
C9 C8 1.511(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.372(8) . ?
C16 H16 0.9500 . ?
C16 C15 1.394(6) . ?
C15 H15 0.9500 . ?
C13 H13 0.9500 . ?
C18 H18 0.9500 . ?
C18 C8 1.313(7) . ?
C5 H5 0.9500 . ?
C5 C4 1.392(8) . ?
C8 H8 0.9500 . ?
C20 H20 0.9500 . ?
C20 C21 1.386(7) . ?
C24 H24 0.9500 . ?
C24 C23 1.398(8) . ?
C21 H21 0.9500 . ?
C21 C22 1.364(9) . ?
C22 H22 0.9500 . ?
C22 C23 1.388(10) . ?
C23 H23 0.9500 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C27 1.484(9) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.494(9) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.511(12) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
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
O2 C10 C17 F2 -47.7(6) . . . . ?
O2 C10 C17 F3 72.7(6) . . . . ?
O2 C10 C17 F1 -167.6(4) . . . . ?
O2 C10 C9 N1 -66.8(5) . . . . ?
O2 C10 C9 C8 54.5(6) . . . . ?
O3 C28 C27 C26 -34.1(7) . . . . ?
O3 C25 C26 C27 -5.8(8) . . . . ?
N1 C9 C8 C18 -113.0(6) . . . . ?
C11 C10 C17 F2 -165.9(5) . . . . ?
C11 C10 C17 F3 -45.5(7) . . . . ?
C11 C10 C17 F1 74.2(6) . . . . ?
C11 C10 C9 N1 59.1(5) . . . . ?
C11 C10 C9 C8 -179.5(4) . . . . ?
C11 C12 C13 C14 -1.1(7) . . . . ?
C11 C16 C15 C14 -1.2(7) . . . . ?
C10 C11 C12 C13 -178.2(4) . . . . ?
C10 C11 C16 C15 179.3(4) . . . . ?
C10 C9 C8 C18 125.2(6) . . . . ?
C1 C2 C3 C4 -2.5(8) . . . . ?
C1 C6 C5 C4 -0.6(7) . . . . ?
C17 C10 C9 N1 -179.8(4) . . . . ?
C17 C10 C9 C8 -58.4(6) . . . . ?
C12 C11 C10 O2 -38.4(6) . . . . ?
C12 C11 C10 C17 74.6(6) . . . . ?
C12 C11 C10 C9 -164.0(4) . . . . ?
C12 C11 C16 C15 0.4(7) . . . . ?
C2 C1 C6 C5 -1.2(7) . . . . ?
C2 C1 C7 O1 -34.0(7) . . . . ?
C2 C1 C7 N1 144.3(5) . . . . ?
C2 C3 C4 Br1 -178.4(4) . . . . ?
C2 C3 C4 C5 0.5(8) . . . . ?
C6 C1 C2 C3 2.8(7) . . . . ?
C6 C1 C7 O1 145.1(5) . . . . ?
C6 C1 C7 N1 -36.6(6) . . . . ?
C6 C5 C4 Br1 180.0(3) . . . . ?
C6 C5 C4 C3 1.0(8) . . . . ?
C19 C18 C8 C9 171.9(5) . . . . ?
C19 C20 C21 C22 -0.5(9) . . . . ?
C19 C24 C23 C22 -0.2(10) . . . . ?
C9 N1 C7 O1 4.8(7) . . . . ?
C9 N1 C7 C1 -173.4(4) . . . . ?
C9 C10 C17 F2 70.0(6) . . . . ?
C9 C10 C17 F3 -169.5(5) . . . . ?
C9 C10 C17 F1 -49.9(6) . . . . ?
C7 N1 C9 C10 -133.7(5) . . . . ?
C7 N1 C9 C8 100.8(5) . . . . ?
C7 C1 C2 C3 -178.1(5) . . . . ?
C7 C1 C6 C5 179.7(4) . . . . ?
C16 C11 C10 O2 142.7(5) . . . . ?
C16 C11 C10 C17 -104.3(5) . . . . ?
C16 C11 C10 C9 17.1(6) . . . . ?
C16 C11 C12 C13 0.8(7) . . . . ?
C15 C14 C13 C12 0.4(8) . . . . ?
C13 C14 C15 C16 0.8(7) . . . . ?
C18 C19 C20 C21 178.2(5) . . . . ?
C18 C19 C24 C23 -177.8(6) . . . . ?
C20 C19 C18 C8 -179.9(6) . . . . ?
C20 C19 C24 C23 0.0(9) . . . . ?
C20 C21 C22 C23 0.3(10) . . . . ?
C24 C19 C18 C8 -2.1(9) . . . . ?
C24 C19 C20 C21 0.4(9) . . . . ?
C21 C22 C23 C24 0.0(10) . . . . ?
C28 O3 C25 C26 -15.8(8) . . . . ?
C25 O3 C28 C27 31.4(7) . . . . ?
C25 C26 C27 C28 24.2(8) . . . . ?
