#------------------------------------------------------------------------------
#$Date: 2025-03-04 20:45:26 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298065 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/38/1573800.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_1573800
loop_
_publ_author_name
'Hu, Yue-Hong'
'Chen, Yu-Ting'
'He, Zhi-Juan'
'Gan, Zhang-Yan'
'Zhang, Ling-Hui'
'Xi, Wen-Jie'
'Li, Baosheng'
'Zhang, Fu-Min'
_publ_section_title
;
 One-pot Nazarov cyclization/oxidative 1,2-carbon rearrangement/Ritter
 reaction to access 5-quaternary-4-amidocyclopent-2-enones and
 2-quaternary-3-amidoindanones.
;
_journal_issue                   18
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3720
_journal_page_last               3723
_journal_paper_doi               10.1039/d4cc06597b
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C21 H19 Br2 N O2'
_chemical_formula_sum            'C21 H19 Br2 N O2'
_chemical_formula_weight         477.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-13
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-12-13 deposited with the CCDC.	2025-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.0437(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.9874(2)
_cell_length_b                   9.81932(13)
_cell_length_c                   24.6758(3)
_cell_measurement_reflns_used    10373
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      75.8830
_cell_measurement_theta_min      3.7870
_cell_volume                     3890.77(9)
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00 -25.00   0.50    0.05    -- -100.00  45.00 120.00   58
  2  ω    -52.00 -25.00   0.50    0.05    -- -100.00  45.00  60.00   54
  3  ω    -54.00 -29.00   0.50    0.05    -- -100.00  45.00   0.00   50
  4  ω    -50.00 -25.00   0.50    0.05    -- -100.00  45.00  30.00   50
  5  ω    -54.00 -25.00   0.50    0.05    -- -100.00  45.00 -30.00   58
  6  ω    -74.00 -32.00   0.50    0.05    -- -100.00  61.00-120.00   84
  7  ω    -44.00  27.00   0.50    0.05    --  -44.63  37.00 120.00  142
  8  ω    -33.00  23.00   0.50    0.05    --   44.63 -19.00 -30.00  112
  9  ω    -31.00  39.00   0.50    0.05    --   44.63 -37.00-120.00  140
 10  ω     43.00  68.00   0.50    0.05    --  108.93 -61.00-150.00   50
 11  ω     69.00 107.00   0.50    0.05    --   44.63 145.00  39.00   76
 12  ω     83.00 131.00   0.50    0.05    --  108.93 126.00-128.00   96
 13  ω    135.00 169.00   0.50    0.05    --  108.93 126.00-128.00   68
 14  ω    144.00 175.00   0.50    0.05    --  108.93  61.00-150.00   62
 15  ω     92.00 129.00   0.50    0.05    --  108.93  61.00-150.00   74
 16  ω     96.00 160.00   0.50    0.05    --  108.93  45.00  30.00  128
 17  ω     37.00  64.00   0.50    0.05    --  108.93 -94.00 150.00   54
 18  ω     50.00  75.00   0.50    0.05    --  108.93-126.00 153.00   50
 19  ω     56.00 125.00   0.50    0.05    --  108.93-145.00 -13.00  138
 20  ω     70.00 101.00   0.50    0.05    --  108.93 -94.00 -60.00   62
 21  ω    -71.00 -46.00   0.50    0.05    --  -44.63 145.00  39.00   50
 22  ω    -92.00 -66.00   0.50    0.05    -- -100.00 137.00 116.16   52
 23  ω   -120.00 -95.00   0.50    0.05    -- -100.00 137.00 116.16   50
 24  ω   -112.00 -65.00   0.50    0.05    -- -100.00 125.00 150.00   94
 25  ω    -65.00 -39.00   0.50    0.05    -- -100.00 125.00 120.00   52
 26  ω   -110.00 -76.00   0.50    0.05    -- -100.00 125.00 120.00   68
 27  ω   -105.00 -79.00   0.50    0.05    -- -100.00 145.00  39.00   52
 28  ω    -95.00 -59.00   0.50    0.05    --  -44.63 126.00-128.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0037191000
_diffrn_orient_matrix_UB_12      -0.1526496000
_diffrn_orient_matrix_UB_13      -0.0150533000
_diffrn_orient_matrix_UB_21      0.0428617000
_diffrn_orient_matrix_UB_22      -0.0346228000
_diffrn_orient_matrix_UB_23      0.0637604000
_diffrn_orient_matrix_UB_31      -0.0857509000
_diffrn_orient_matrix_UB_32      -0.0106764000
_diffrn_orient_matrix_UB_33      0.0084070000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12974
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.096
_diffrn_reflns_theta_min         3.790
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.404
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.629
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.775
_refine_diff_density_min         -1.181
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.00024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3856
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0525P)²+12.0932P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1044
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3623
_reflns_number_total             3856
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc06597b3.cif
_cod_data_source_block           huyh_1211_auto
_cod_depositor_comments
'Adding full bibliography for 1573796--1573800.cif.'
_cod_original_cell_volume        3890.75(10)
_cod_database_code               1573800
_shelx_shelxl_version_number     2018/3
_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   0.813
_shelx_estimated_absorpt_t_min   0.345
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C15(H15), C16(H16), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.113
_oxdiff_exptl_absorpt_empirical_full_min 0.394
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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
Br1 Br 0.63864(2) 0.64313(5) 0.99733(2) 0.05195(16) Uani 1 1 d . . . . .
Br2 Br 0.08193(2) 0.68436(4) 0.50242(2) 0.04780(15) Uani 1 1 d . . . . .
O1 O 0.56323(12) 0.2439(2) 0.74543(9) 0.0342(4) Uani 1 1 d . . . . .
O2 O 0.25475(12) 0.40751(19) 0.80564(8) 0.0295(4) Uani 1 1 d . . . . .
N1 N 0.34179(12) 0.5047(2) 0.76416(8) 0.0178(4) Uani 1 1 d . . . . .
H1 H 0.3677(18) 0.569(3) 0.7623(13) 0.019(7) Uiso 1 1 d . . . . .
C1 C 0.44888(15) 0.3125(2) 0.77867(11) 0.0215(5) Uani 1 1 d . . . . .
C2 C 0.36416(14) 0.3790(2) 0.74217(10) 0.0186(5) Uani 1 1 d . . . . .
H2 H 0.318546 0.311254 0.737841 0.022 Uiso 1 1 calc R U . . .
C3 C 0.37347(15) 0.4028(2) 0.68374(10) 0.0206(5) Uani 1 1 d . . . . .
C4 C 0.44700(16) 0.3606(2) 0.68053(11) 0.0240(5) Uani 1 1 d . . . . .
C5 C 0.49589(15) 0.3008(2) 0.73548(11) 0.0242(5) Uani 1 1 d . . . . .
C6 C 0.49740(15) 0.3945(2) 0.83148(10) 0.0221(5) Uani 1 1 d . . . . .
C7 C 0.46456(16) 0.4104(3) 0.87618(11) 0.0277(5) Uani 1 1 d . . . . .
H7 H 0.412873 0.368674 0.873230 0.033 Uiso 1 1 calc R U . . .
C8 C 0.50554(17) 0.4854(3) 0.92456(11) 0.0331(6) Uani 1 1 d . . . . .
H8 H 0.481078 0.498416 0.953739 0.040 Uiso 1 1 calc R U . . .
C9 C 0.58228(16) 0.5413(3) 0.93009(11) 0.0324(6) Uani 1 1 d . . . . .
C10 C 0.61749(16) 0.5275(3) 0.88715(12) 0.0316(6) Uani 1 1 d . . . . .
H10 H 0.670189 0.566852 0.891142 0.038 Uiso 1 1 calc R U . . .
C11 C 0.57432(16) 0.4551(3) 0.83803(11) 0.0259(5) Uani 1 1 d . . . . .
H11 H 0.597776 0.446616 0.808114 0.031 Uiso 1 1 calc R U . . .
C12 C 0.43375(18) 0.1668(3) 0.79612(13) 0.0317(6) Uani 1 1 d . . . . .
H12A H 0.487237 0.119874 0.812265 0.048 Uiso 1 1 calc R U . . .
H12B H 0.398986 0.117157 0.762328 0.048 Uiso 1 1 calc R U . . .
H12C H 0.405393 0.170631 0.824889 0.048 Uiso 1 1 calc R U . . .
C13 C 0.4795(2) 0.3616(3) 0.63078(13) 0.0337(6) Uani 1 1 d . . . . .
H13A H 0.435726 0.393432 0.596347 0.051 Uiso 1 1 calc R U . . .
H13B H 0.496393 0.269224 0.624277 0.051 Uiso 1 1 calc R U . . .
H13C H 0.527613 0.422705 0.639236 0.051 Uiso 1 1 calc R U . . .
C14 C 0.30448(16) 0.4669(3) 0.63806(10) 0.0233(5) Uani 1 1 d . . . . .
C15 C 0.22476(17) 0.4107(3) 0.62204(12) 0.0309(6) Uani 1 1 d . . . . .
H15 H 0.215673 0.328962 0.639751 0.037 Uiso 1 1 calc R U . . .
C16 C 0.15865(18) 0.4722(3) 0.58069(12) 0.0348(6) Uani 1 1 d . . . . .
H16 H 0.104739 0.432378 0.569364 0.042 Uiso 1 1 calc R U . . .
C17 C 0.17258(17) 0.5924(3) 0.55626(11) 0.0319(6) Uani 1 1 d . . . . .
C18 C 0.25057(19) 0.6504(3) 0.57093(11) 0.0325(6) Uani 1 1 d . . . . .
H18 H 0.258991 0.732821 0.553434 0.039 Uiso 1 1 calc R U . . .
C19 C 0.31674(17) 0.5865(3) 0.61170(11) 0.0280(5) Uani 1 1 d . . . . .
H19 H 0.370933 0.624915 0.621659 0.034 Uiso 1 1 calc R U . . .
C20 C 0.29057(14) 0.5086(3) 0.79595(10) 0.0214(5) Uani 1 1 d . . . . .
C21 C 0.28129(19) 0.6465(3) 0.81987(13) 0.0328(6) Uani 1 1 d . . . . .
H21A H 0.223024 0.675677 0.804567 0.049 Uiso 1 1 calc R U . . .
H21B H 0.316636 0.712467 0.808838 0.049 Uiso 1 1 calc R U . . .
H21C H 0.298185 0.641198 0.861769 0.049 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'
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 N1 H1 117(2) . . ?
C20 N1 H1 120(2) . . ?
C20 N1 C2 122.7(2) . . ?
C5 C1 C2 102.76(19) . . ?
C5 C1 C12 107.3(2) . . ?
C6 C1 C2 114.17(19) . . ?
C6 C1 C5 112.1(2) . . ?
C6 C1 C12 110.2(2) . . ?
C12 C1 C2 110.0(2) . . ?
N1 C2 C1 116.31(19) . . ?
N1 C2 H2 108.6 . . ?
N1 C2 C3 110.20(19) . . ?
C1 C2 H2 108.6 . . ?
C3 C2 C1 104.41(18) . . ?
C3 C2 H2 108.6 . . ?
C4 C3 C2 113.3(2) . . ?
C4 C3 C14 127.5(2) . . ?
C14 C3 C2 119.2(2) . . ?
C3 C4 C5 109.1(2) . . ?
C3 C4 C13 130.1(3) . . ?
C5 C4 C13 120.8(2) . . ?
O1 C5 C1 124.1(2) . . ?
O1 C5 C4 125.5(2) . . ?
C4 C5 C1 110.4(2) . . ?
C7 C6 C1 119.3(2) . . ?
C11 C6 C1 123.3(2) . . ?
C11 C6 C7 117.4(2) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.5(2) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.4(2) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 Br1 119.0(2) . . ?
C8 C9 C10 121.1(3) . . ?
C10 C9 Br1 119.9(2) . . ?
C9 C10 H10 120.6 . . ?
C9 C10 C11 118.7(2) . . ?
C11 C10 H10 120.6 . . ?
C6 C11 H11 119.1 . . ?
C10 C11 C6 121.8(2) . . ?
C10 C11 H11 119.1 . . ?
C1 C12 H12A 109.5 . . ?
C1 C12 H12B 109.5 . . ?
C1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C4 C13 H13A 109.5 . . ?
C4 C13 H13B 109.5 . . ?
C4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C3 120.2(2) . . ?
C19 C14 C3 121.0(2) . . ?
C19 C14 C15 118.8(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.8(3) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 Br2 119.7(2) . . ?
C18 C17 Br2 118.5(2) . . ?
C18 C17 C16 121.7(3) . . ?
C17 C18 H18 120.5 . . ?
C17 C18 C19 119.0(3) . . ?
C19 C18 H18 120.5 . . ?
C14 C19 H19 119.7 . . ?
C18 C19 C14 120.7(3) . . ?
C18 C19 H19 119.7 . . ?
O2 C20 N1 123.0(2) . . ?
O2 C20 C21 121.9(2) . . ?
N1 C20 C21 115.0(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
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 C9 1.906(3) . ?
Br2 C17 1.902(3) . ?
O1 C5 1.224(3) . ?
O2 C20 1.228(3) . ?
N1 H1 0.78(3) . ?
N1 C2 1.449(3) . ?
N1 C20 1.349(3) . ?
C1 C2 1.569(3) . ?
C1 C5 1.530(3) . ?
C1 C6 1.525(3) . ?
C1 C12 1.540(3) . ?
C2 H2 1.0000 . ?
C2 C3 1.519(3) . ?
C3 C4 1.343(3) . ?
C3 C14 1.476(3) . ?
C4 C5 1.462(4) . ?
C4 C13 1.501(3) . ?
C6 C7 1.398(3) . ?
C6 C11 1.396(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.382(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.380(4) . ?
C9 C10 1.383(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(4) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.395(4) . ?
C14 C19 1.390(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.381(4) . ?
C17 C18 1.377(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.390(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.506(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
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
Br1 C9 C10 C11 -178.7(2) . . . . ?
Br2 C17 C18 C19 177.8(2) . . . . ?
N1 C2 C3 C4 126.4(2) . . . . ?
N1 C2 C3 C14 -53.6(3) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C1 C2 C3 C14 -179.2(2) . . . . ?
C1 C6 C7 C8 -179.0(2) . . . . ?
C1 C6 C11 C10 -179.0(2) . . . . ?
C2 N1 C20 O2 -4.8(4) . . . . ?
C2 N1 C20 C21 174.2(2) . . . . ?
C2 C1 C5 O1 -174.1(2) . . . . ?
C2 C1 C5 C4 3.0(3) . . . . ?
C2 C1 C6 C7 66.2(3) . . . . ?
C2 C1 C6 C11 -114.2(3) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C2 C3 C4 C13 177.9(2) . . . . ?
C2 C3 C14 C15 -55.3(3) . . . . ?
C2 C3 C14 C19 122.4(2) . . . . ?
C3 C4 C5 O1 174.4(2) . . . . ?
C3 C4 C5 C1 -2.7(3) . . . . ?
C3 C14 C15 C16 177.7(2) . . . . ?
C3 C14 C19 C18 -176.5(2) . . . . ?
C4 C3 C14 C15 124.7(3) . . . . ?
C4 C3 C14 C19 -57.6(4) . . . . ?
C5 C1 C2 N1 -123.9(2) . . . . ?
C5 C1 C2 C3 -2.2(2) . . . . ?
C5 C1 C6 C7 -177.5(2) . . . . ?
C5 C1 C6 C11 2.1(3) . . . . ?
C6 C1 C2 N1 -2.3(3) . . . . ?
C6 C1 C2 C3 119.3(2) . . . . ?
C6 C1 C5 O1 62.9(3) . . . . ?
C6 C1 C5 C4 -120.0(2) . . . . ?
C6 C7 C8 C9 -2.8(4) . . . . ?
C7 C6 C11 C10 0.6(4) . . . . ?
C7 C8 C9 Br1 -179.4(2) . . . . ?
C7 C8 C9 C10 2.3(4) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C9 C10 C11 C6 -1.0(4) . . . . ?
C11 C6 C7 C8 1.3(4) . . . . ?
C12 C1 C2 N1 122.1(2) . . . . ?
C12 C1 C2 C3 -116.2(2) . . . . ?
C12 C1 C5 O1 -58.2(3) . . . . ?
C12 C1 C5 C4 118.9(2) . . . . ?
C12 C1 C6 C7 -58.2(3) . . . . ?
C12 C1 C6 C11 121.5(3) . . . . ?
C13 C4 C5 O1 -2.8(4) . . . . ?
C13 C4 C5 C1 -179.8(2) . . . . ?
C14 C3 C4 C5 -178.9(2) . . . . ?
C14 C3 C4 C13 -2.0(4) . . . . ?
C14 C15 C16 C17 -1.4(4) . . . . ?
C15 C14 C19 C18 1.2(4) . . . . ?
C15 C16 C17 Br2 -176.6(2) . . . . ?
C15 C16 C17 C18 1.6(4) . . . . ?
C16 C17 C18 C19 -0.5(4) . . . . ?
C17 C18 C19 C14 -1.0(4) . . . . ?
C19 C14 C15 C16 0.0(4) . . . . ?
C20 N1 C2 C1 -96.4(3) . . . . ?
C20 N1 C2 C3 145.1(2) . . . . ?
