#------------------------------------------------------------------------------
#$Date: 2021-03-03 22:34:47 +0200 (Wed, 03 Mar 2021) $
#$Revision: 262408 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/85/4518523.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_4518523
loop_
_publ_author_name
'Gao, Can'
'Wang, Xunhua'
'Liu, Jitian'
'Li, Xiaoxun'
_publ_section_title
;
 Highly Diastereo- and Enantioselective Synthesis of
 Tetrahydrobenzo[b]azocines via Palladium-Catalyzed [4 + 4] Cycloaddition
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              2684
_journal_page_last               2690
_journal_paper_doi               10.1021/acscatal.0c05515
_journal_year                    2021
_chemical_absolute_configuration syn
_chemical_formula_moiety         '2(C20 H17 Br4 N O3)'
_chemical_formula_sum            'C40 H34 Br8 N2 O6'
_chemical_formula_weight         1277.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-10-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.756(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.1259(9)
_cell_length_b                   7.5367(3)
_cell_length_c                   20.6213(5)
_cell_measurement_reflns_used    7606
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      75.9110
_cell_measurement_theta_min      3.2180
_cell_volume                     4227.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (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      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    100.00 178.00   1.00    1.20    --  106.49  38.00   0.00   78
  2  ω     94.00 178.00   1.00    1.20    --  106.49  19.00 -30.00   84
  3  ω     54.00  79.00   1.00    0.27    --   48.45  39.00 -99.00   25
  4  ω    100.00 137.00   1.00    1.20    --  106.49  39.00 -99.00   37
  5  ω     94.00 178.00   1.00    1.20    --  106.49  19.00-120.00   84
  6  ω     37.00 105.00   1.00    1.20    --  106.49 -77.00 -30.00   68
  7  ω     34.00  65.00   1.00    1.20    --  106.49 -57.00   0.00   31
  8  ω     34.00  66.00   1.00    1.20    --  106.49 -57.00  30.00   32
  9  ω     34.00  66.00   1.00    1.20    --  106.49 -57.00 150.00   32
 10  ω    -24.00  43.00   1.00    0.27    --   48.45 -39.00 105.00   67
 11  ω    -42.00  25.00   1.00    0.27    --  -48.45  38.00 -30.00   67
 12  ω    -43.00  24.00   1.00    0.27    --  -48.45  39.00 -99.00   67
 13  ω    -44.00 -19.00   1.00    1.20    --  -86.25  39.00 -99.00   25
 14  ω    -63.00 -14.00   1.00    1.20    --  -86.25  57.00  60.00   49
 15  ω   -120.00 -36.00   1.00    0.27    --  -48.45 -39.00 105.00   84
 16  ω   -140.00-115.00   1.00    1.20    --  -86.25 -39.00 105.00   25
 17  ω   -152.00 -73.00   1.00    1.20    --  -86.25 -38.00 120.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0032017000
_diffrn_orient_matrix_UB_12      -0.1002935000
_diffrn_orient_matrix_UB_13      -0.0660763000
_diffrn_orient_matrix_UB_21      0.0565823000
_diffrn_orient_matrix_UB_22      -0.0055216000
_diffrn_orient_matrix_UB_23      0.0160178000
_diffrn_orient_matrix_UB_31      0.0000133000
_diffrn_orient_matrix_UB_32      -0.1779502000
_diffrn_orient_matrix_UB_33      0.0366712000
_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  0.0352
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12929
_diffrn_reflns_point_group_measured_fraction_full 0.794
_diffrn_reflns_point_group_measured_fraction_max 0.794
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         3.250
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.481
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    2.008
_exptl_crystal_description       block
_exptl_crystal_F_000             2464
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 1811 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.022(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         5994
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0258
_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)+(0.0287P)²+1.5597P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0634
_refine_ls_wR_factor_ref         0.0642
_reflns_Friedel_coverage         0.487
_reflns_Friedel_fraction_full    0.567
_reflns_Friedel_fraction_max     0.567
_reflns_number_gt                5702
_reflns_number_total             5994
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c05515_si_003.cif
_cod_data_source_block           201009c
_cod_database_code               4518523
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CNO
_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   0.833
_shelx_estimated_absorpt_t_min   0.764
_reflns_odcompleteness_completeness 98.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Ternary CH refined with riding coordinates:
 C13(H13), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C28(H28A,H28B), C29(H29A,H29B), C19(H19A,H19B), C33(H33A,
 H33B), C37(H37A,H37B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C14(H14), C25(H25), C27(H27), C35(H35), C36(H36), C40(H40), N2(H2),
 C18(H18), C24(H24), C26(H26), C30(H30), C31(H31), C34(H34)
2.d Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C39(H39A,H39B,H39C)
;
_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 1.595
_oxdiff_exptl_absorpt_empirical_full_min 0.724
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-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 0.51974(2) 0.32746(10) 0.41522(3) 0.03751(16) Uani 1 1 d . . . . .
Br2 Br 0.54829(2) 0.23225(10) 0.07162(3) 0.03856(16) Uani 1 1 d . . . . .
Br5 Br 0.72143(2) 0.24898(13) 0.55817(3) 0.0495(2) Uani 1 1 d . . . . .
Br7 Br 0.60336(2) 0.28378(12) 0.55884(3) 0.0476(2) Uani 1 1 d . . . . .
O3 O 0.66395(13) 0.7095(6) 0.35944(19) 0.0296(9) Uani 1 1 d . . . . .
O4 O 0.65822(11) 0.2375(6) 0.24727(17) 0.0244(8) Uani 1 1 d . . . . .
O5 O 0.59350(13) 0.7603(6) 0.2820(2) 0.0334(9) Uani 1 1 d . . . . .
N1 N 0.56589(15) 0.3309(7) 0.2942(2) 0.0272(10) Uani 1 1 d . . . . .
H1 H 0.540856 0.404269 0.289023 0.033 Uiso 1 1 calc R U . . .
C1 C 0.63169(18) 0.6834(8) 0.3001(3) 0.0233(12) Uani 1 1 d . . . . .
C7 C 0.60074(18) 0.3225(8) 0.3556(3) 0.0226(10) Uani 1 1 d . . . . .
C10 C 0.60980(17) 0.2816(8) 0.2054(2) 0.0239(12) Uani 1 1 d . . . . .
C11 C 0.65124(18) 0.3317(9) 0.3582(3) 0.0253(11) Uani 1 1 d . . . . .
C12 C 0.6720(2) 0.2881(9) 0.4781(3) 0.0323(14) Uani 1 1 d . . . . .
C13 C 0.67050(18) 0.3725(8) 0.2977(3) 0.0228(11) Uani 1 1 d . . . . .
H13 H 0.707161 0.379262 0.313107 0.027 Uiso 1 1 calc R U . . .
C14 C 0.7274(2) 0.5386(9) 0.2111(3) 0.0320(14) Uani 1 1 d . . . . .
H14 H 0.727319 0.413048 0.214959 0.038 Uiso 1 1 calc R U . . .
C15 C 0.58721(18) 0.3160(9) 0.4167(3) 0.0258(11) Uani 1 1 d . . . . .
C20 C 0.57054(18) 0.2197(8) 0.2388(3) 0.0261(12) Uani 1 1 d . . . . .
H20A H 0.538527 0.216564 0.204862 0.031 Uiso 1 1 calc R U . . .
H20B H 0.578318 0.097135 0.255428 0.031 Uiso 1 1 calc R U . . .
C22 C 0.6929(2) 0.6399(8) 0.2340(3) 0.0255(12) Uani 1 1 d . . . . .
C23 C 0.6221(2) 0.2996(9) 0.4774(3) 0.0334(13) Uani 1 1 d . . . . .
C25 C 0.6944(2) 0.8232(9) 0.2277(3) 0.0338(14) Uani 1 1 d . . . . .
H25 H 0.671999 0.894425 0.243766 0.041 Uiso 1 1 calc R U . . .
C27 C 0.68566(19) 0.3106(9) 0.4195(3) 0.0280(12) Uani 1 1 d . . . . .
H27 H 0.719649 0.311911 0.420754 0.034 Uiso 1 1 calc R U . . .
C28 C 0.6112(2) 0.4826(8) 0.1972(3) 0.0250(11) Uani 1 1 d . . . . .
H28A H 0.579078 0.536040 0.197056 0.030 Uiso 1 1 calc R U . . .
H28B H 0.619561 0.513939 0.154726 0.030 Uiso 1 1 calc R U . . .
C29 C 0.6077(2) 0.1773(9) 0.1412(3) 0.0352(14) Uani 1 1 d . . . . .
H29A H 0.608524 0.048633 0.151164 0.042 Uiso 1 1 calc R U . . .
H29B H 0.636907 0.206195 0.124760 0.042 Uiso 1 1 calc R U . . .
C32 C 0.65173(18) 0.5480(7) 0.2583(3) 0.0215(11) Uani 1 1 d . . . . .
C35 C 0.7613(2) 0.6207(10) 0.1829(3) 0.0362(15) Uani 1 1 d . . . . .
H35 H 0.784867 0.551228 0.168504 0.043 Uiso 1 1 calc R U . . .
C36 C 0.7612(2) 0.8033(11) 0.1756(3) 0.0415(16) Uani 1 1 d . . . . .
H36 H 0.783875 0.858996 0.155066 0.050 Uiso 1 1 calc R U . . .
C38 C 0.6485(2) 0.8285(11) 0.4058(3) 0.0443(17) Uani 1 1 d . . . . .
H38A H 0.676872 0.857564 0.442996 0.066 Uiso 1 1 calc R U . . .
H38B H 0.623219 0.770445 0.423321 0.066 Uiso 1 1 calc R U . . .
H38C H 0.635144 0.937595 0.382261 0.066 Uiso 1 1 calc R U . . .
C40 C 0.7278(3) 0.9035(10) 0.1985(4) 0.0473(18) Uani 1 1 d . . . . .
H40 H 0.727750 1.028933 0.194094 0.057 Uiso 1 1 calc R U . . .
Br3 Br 0.40853(2) 0.75312(10) -0.04000(3) 0.04148(17) Uani 1 1 d . . . . .
Br4 Br 0.51487(2) 0.82947(11) 0.37553(3) 0.04219(17) Uani 1 1 d . . . . .
Br6 Br 0.42923(2) 0.78748(12) 0.45675(3) 0.0483(2) Uani 1 1 d . . . . .
Br8 Br 0.31262(2) 0.71649(14) 0.36771(3) 0.0551(2) Uani 1 1 d . . . . .
O1 O 0.37775(12) 0.3108(6) 0.21722(18) 0.0272(8) Uani 1 1 d . . . . .
O2 O 0.39205(12) 0.7778(5) 0.10967(16) 0.0224(8) Uani 1 1 d . . . . .
O6 O 0.45614(13) 0.2835(6) 0.2130(2) 0.0356(10) Uani 1 1 d . . . . .
N2 N 0.47974(14) 0.7238(7) 0.2296(2) 0.0266(10) Uani 1 1 d . . . . .
H2 H 0.505960 0.660576 0.248270 0.032 Uiso 1 1 calc R U . . .
C2 C 0.41592(19) 0.3461(8) 0.1913(3) 0.0243(12) Uani 1 1 d . . . . .
C3 C 0.39988(18) 0.4687(7) 0.1313(3) 0.0207(11) Uani 1 1 d . . . . .
C4 C 0.4134(2) 0.7581(9) 0.3632(2) 0.0293(12) Uani 1 1 d . . . . .
C5 C 0.37780(19) 0.6468(7) 0.1508(3) 0.0211(11) Uani 1 1 d . . . . .
H5 H 0.341144 0.636796 0.136926 0.025 Uiso 1 1 calc R U . . .
C6 C 0.3654(2) 0.7261(9) 0.3267(3) 0.0296(13) Uani 1 1 d . . . . .
C8 C 0.39281(18) 0.6960(7) 0.2246(3) 0.0203(11) Uani 1 1 d . . . . .
C9 C 0.44138(17) 0.7318(8) 0.2605(3) 0.0228(11) Uani 1 1 d . . . . .
C16 C 0.44992(19) 0.7634(8) 0.3292(2) 0.0271(12) Uani 1 1 d . . . . .
C17 C 0.44116(17) 0.7367(9) 0.1060(3) 0.0249(11) Uani 1 1 d . . . . .
C18 C 0.3273(2) 0.1015(9) 0.0203(3) 0.0346(14) Uani 1 1 d . . . . .
H18 H 0.327081 -0.024447 0.018550 0.042 Uiso 1 1 calc R U . . .
C19 C 0.47786(19) 0.8174(9) 0.1670(3) 0.0290(12) Uani 1 1 d . . . . .
H19A H 0.511042 0.816283 0.158786 0.035 Uiso 1 1 calc R U . . .
H19B H 0.468756 0.942643 0.171819 0.035 Uiso 1 1 calc R U . . .
C21 C 0.36174(19) 0.3726(8) 0.0759(3) 0.0227(12) Uani 1 1 d . . . . .
C24 C 0.35532(19) 0.6986(8) 0.2585(3) 0.0260(12) Uani 1 1 d . . . . .
H24 H 0.322213 0.680868 0.233850 0.031 Uiso 1 1 calc R U . . .
C26 C 0.3611(2) 0.1890(8) 0.0713(3) 0.0294(13) Uani 1 1 d . . . . .
H26 H 0.384206 0.121741 0.103613 0.035 Uiso 1 1 calc R U . . .
C30 C 0.3283(2) 0.4675(9) 0.0267(3) 0.0296(13) Uani 1 1 d . . . . .
H30 H 0.328432 0.593530 0.028057 0.035 Uiso 1 1 calc R U . . .
C31 C 0.2947(2) 0.3797(9) -0.0243(3) 0.0372(15) Uani 1 1 d . . . . .
H31 H 0.271905 0.446170 -0.057276 0.045 Uiso 1 1 calc R U . . .
C33 C 0.4504(2) 0.8315(9) 0.0449(3) 0.0306(13) Uani 1 1 d . . . . .
H33A H 0.485142 0.812932 0.044260 0.037 Uiso 1 1 calc R U . . .
H33B H 0.445506 0.960435 0.049608 0.037 Uiso 1 1 calc R U . . .
C34 C 0.2942(2) 0.1972(10) -0.0275(3) 0.0379(16) Uani 1 1 d . . . . .
H34 H 0.271191 0.137815 -0.062531 0.045 Uiso 1 1 calc R U . . .
C37 C 0.4438(2) 0.5334(8) 0.1054(3) 0.0247(12) Uani 1 1 d . . . . .
H37A H 0.475210 0.491274 0.134967 0.030 Uiso 1 1 calc R U . . .
H37B H 0.441084 0.489156 0.059351 0.030 Uiso 1 1 calc R U . . .
C39 C 0.3876(2) 0.1966(9) 0.2751(3) 0.0378(15) Uani 1 1 d . . . . .
H39A H 0.415455 0.243584 0.309479 0.057 Uiso 1 1 calc R U . . .
H39B H 0.395446 0.077164 0.262195 0.057 Uiso 1 1 calc R U . . .
H39C H 0.358471 0.191431 0.292943 0.057 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
C1 O3 C38 116.4(4) . . ?
C13 O4 C10 106.6(4) . . ?
C7 N1 H1 119.8 . . ?
C7 N1 C20 120.4(5) . . ?
C20 N1 H1 119.8 . . ?
O3 C1 C32 110.5(4) . . ?
O5 C1 O3 124.1(5) . . ?
O5 C1 C32 125.3(5) . . ?
N1 C7 C11 120.1(4) . . ?
N1 C7 C15 121.9(4) . . ?
C15 C7 C11 117.9(5) . . ?
O4 C10 C20 109.9(4) . . ?
O4 C10 C28 104.2(4) . . ?
O4 C10 C29 102.8(4) . . ?
C20 C10 C28 113.5(5) . . ?
C20 C10 C29 111.3(5) . . ?
C28 C10 C29 114.3(5) . . ?
C7 C11 C13 123.2(5) . . ?
C27 C11 C7 119.3(5) . . ?
C27 C11 C13 117.4(4) . . ?
C23 C12 Br5 122.0(4) . . ?
C27 C12 Br5 118.7(4) . . ?
C27 C12 C23 119.2(5) . . ?
O4 C13 C11 112.5(5) . . ?
O4 C13 H13 107.8 . . ?
O4 C13 C32 103.7(4) . . ?
C11 C13 H13 107.8 . . ?
C11 C13 C32 117.0(4) . . ?
C32 C13 H13 107.8 . . ?
C22 C14 H14 119.8 . . ?
C35 C14 H14 119.8 . . ?
C35 C14 C22 120.4(6) . . ?
C7 C15 Br1 118.9(4) . . ?
C23 C15 Br1 119.7(4) . . ?
C23 C15 C7 121.4(4) . . ?
N1 C20 C10 113.8(5) . . ?
N1 C20 H20A 108.8 . . ?
N1 C20 H20B 108.8 . . ?
C10 C20 H20A 108.8 . . ?
C10 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C14 C22 C32 120.4(5) . . ?
C25 C22 C14 117.9(5) . . ?
C25 C22 C32 121.4(5) . . ?
C12 C23 Br7 119.5(4) . . ?
C15 C23 Br7 121.0(4) . . ?
C15 C23 C12 119.5(5) . . ?
C22 C25 H25 119.4 . . ?
C40 C25 C22 121.2(6) . . ?
C40 C25 H25 119.4 . . ?
C11 C27 H27 119.0 . . ?
C12 C27 C11 122.0(5) . . ?
C12 C27 H27 119.0 . . ?
C10 C28 H28A 110.7 . . ?
C10 C28 H28B 110.7 . . ?
C10 C28 C32 105.1(4) . . ?
H28A C28 H28B 108.8 . . ?
C32 C28 H28A 110.7 . . ?
C32 C28 H28B 110.7 . . ?
Br2 C29 H29A 109.3 . . ?
Br2 C29 H29B 109.3 . . ?
C10 C29 Br2 111.4(4) . . ?
C10 C29 H29A 109.3 . . ?
C10 C29 H29B 109.3 . . ?
H29A C29 H29B 108.0 . . ?
C1 C32 C13 113.2(4) . . ?
C1 C32 C22 107.4(4) . . ?
C1 C32 C28 111.7(4) . . ?
C22 C32 C13 111.4(4) . . ?
C22 C32 C28 109.6(4) . . ?
C28 C32 C13 103.5(4) . . ?
C14 C35 H35 119.8 . . ?
C14 C35 C36 120.5(6) . . ?
C36 C35 H35 119.8 . . ?
C35 C36 H36 120.3 . . ?
C40 C36 C35 119.4(6) . . ?
C40 C36 H36 120.3 . . ?
O3 C38 H38A 109.5 . . ?
O3 C38 H38B 109.5 . . ?
O3 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C25 C40 C36 120.5(7) . . ?
C25 C40 H40 119.7 . . ?
C36 C40 H40 119.7 . . ?
C2 O1 C39 116.4(4) . . ?
C5 O2 C17 107.6(4) . . ?
C9 N2 H2 119.1 . . ?
C9 N2 C19 121.8(4) . . ?
C19 N2 H2 119.1 . . ?
O1 C2 C3 110.1(4) . . ?
O6 C2 O1 123.0(5) . . ?
O6 C2 C3 126.8(5) . . ?
C2 C3 C5 111.4(4) . . ?
C2 C3 C21 109.0(5) . . ?
C2 C3 C37 112.1(4) . . ?
C21 C3 C5 110.3(4) . . ?
C21 C3 C37 111.1(4) . . ?
C37 C3 C5 102.8(4) . . ?
C6 C4 Br6 121.4(4) . . ?
C16 C4 Br6 120.3(4) . . ?
C16 C4 C6 118.3(5) . . ?
O2 C5 C3 104.5(4) . . ?
O2 C5 H5 107.9 . . ?
O2 C5 C8 112.3(4) . . ?
C3 C5 H5 107.9 . . ?
C8 C5 C3 116.0(4) . . ?
C8 C5 H5 107.9 . . ?
C4 C6 Br8 122.0(4) . . ?
C24 C6 Br8 118.0(4) . . ?
C24 C6 C4 120.0(5) . . ?
C9 C8 C5 124.1(4) . . ?
C9 C8 C24 119.1(5) . . ?
C24 C8 C5 116.8(5) . . ?
N2 C9 C8 121.1(5) . . ?
N2 C9 C16 121.4(5) . . ?
C16 C9 C8 117.4(5) . . ?
C4 C16 Br4 119.7(4) . . ?
C4 C16 C9 123.4(5) . . ?
C9 C16 Br4 116.7(4) . . ?
O2 C17 C19 109.0(4) . . ?
O2 C17 C33 108.1(4) . . ?
O2 C17 C37 105.3(4) . . ?
C33 C17 C19 105.7(4) . . ?
C33 C17 C37 116.2(5) . . ?
C37 C17 C19 112.3(5) . . ?
C26 C18 H18 120.0 . . ?
C34 C18 H18 120.0 . . ?
C34 C18 C26 120.1(6) . . ?
N2 C19 C17 113.5(5) . . ?
N2 C19 H19A 108.9 . . ?
N2 C19 H19B 108.9 . . ?
C17 C19 H19A 108.9 . . ?
C17 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C26 C21 C3 121.1(5) . . ?
C26 C21 C30 117.9(6) . . ?
C30 C21 C3 120.9(5) . . ?
C6 C24 C8 121.6(5) . . ?
C6 C24 H24 119.2 . . ?
C8 C24 H24 119.2 . . ?
C18 C26 H26 119.4 . . ?
C21 C26 C18 121.3(6) . . ?
C21 C26 H26 119.4 . . ?
C21 C30 H30 119.7 . . ?
C31 C30 C21 120.6(6) . . ?
C31 C30 H30 119.7 . . ?
C30 C31 H31 119.7 . . ?
C34 C31 C30 120.6(6) . . ?
C34 C31 H31 119.7 . . ?
Br3 C33 H33A 108.7 . . ?
Br3 C33 H33B 108.7 . . ?
C17 C33 Br3 114.3(4) . . ?
C17 C33 H33A 108.7 . . ?
C17 C33 H33B 108.7 . . ?
H33A C33 H33B 107.6 . . ?
C18 C34 C31 119.5(6) . . ?
C18 C34 H34 120.3 . . ?
C31 C34 H34 120.3 . . ?
C3 C37 H37A 110.6 . . ?
C3 C37 H37B 110.6 . . ?
C17 C37 C3 105.6(4) . . ?
C17 C37 H37A 110.6 . . ?
C17 C37 H37B 110.6 . . ?
H37A C37 H37B 108.8 . . ?
O1 C39 H39A 109.5 . . ?
O1 C39 H39B 109.5 . . ?
O1 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 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 C15 1.892(5) . ?
Br2 C29 1.950(6) . ?
Br5 C12 1.891(5) . ?
Br7 C23 1.888(5) . ?
O3 C1 1.339(7) . ?
O3 C38 1.455(7) . ?
O4 C10 1.453(6) . ?
O4 C13 1.433(7) . ?
O5 C1 1.194(6) . ?
N1 H1 0.8800 . ?
N1 C7 1.391(7) . ?
N1 C20 1.451(7) . ?
C1 C32 1.532(7) . ?
C7 C11 1.410(7) . ?
C7 C15 1.407(7) . ?
C10 C20 1.516(7) . ?
C10 C28 1.526(8) . ?
C10 C29 1.527(8) . ?
C11 C13 1.513(7) . ?
C11 C27 1.393(7) . ?
C12 C23 1.401(8) . ?
C12 C27 1.368(8) . ?
C13 H13 1.0000 . ?
C13 C32 1.571(8) . ?
C14 H14 0.9500 . ?
C14 C22 1.407(8) . ?
C14 C35 1.383(9) . ?
C15 C23 1.386(8) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C22 C25 1.389(9) . ?
C22 C32 1.539(7) . ?
C25 H25 0.9500 . ?
C25 C40 1.377(9) . ?
C27 H27 0.9500 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C32 1.549(7) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C35 H35 0.9500 . ?
C35 C36 1.384(11) . ?
C36 H36 0.9500 . ?
C36 C40 1.379(10) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C40 H40 0.9500 . ?
Br3 C33 1.936(6) . ?
Br4 C16 1.899(5) . ?
Br6 C4 1.879(5) . ?
Br8 C6 1.888(5) . ?
O1 C2 1.343(6) . ?
O1 C39 1.439(7) . ?
O2 C5 1.424(6) . ?
O2 C17 1.436(6) . ?
O6 C2 1.202(6) . ?
N2 H2 0.8800 . ?
N2 C9 1.387(6) . ?
N2 C19 1.460(7) . ?
C2 C3 1.518(8) . ?
C3 C5 1.574(7) . ?
C3 C21 1.535(8) . ?
C3 C37 1.544(7) . ?
C4 C6 1.388(8) . ?
C4 C16 1.384(7) . ?
C5 H5 1.0000 . ?
C5 C8 1.518(7) . ?
C6 C24 1.377(8) . ?
C8 C9 1.404(7) . ?
C8 C24 1.407(7) . ?
C9 C16 1.397(7) . ?
C17 C19 1.535(8) . ?
C17 C33 1.527(7) . ?
C17 C37 1.534(8) . ?
C18 H18 0.9500 . ?
C18 C26 1.391(9) . ?
C18 C34 1.376(10) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C21 C26 1.386(9) . ?
C21 C30 1.393(8) . ?
C24 H24 0.9500 . ?
C26 H26 0.9500 . ?
C30 H30 0.9500 . ?
C30 C31 1.389(9) . ?
C31 H31 0.9500 . ?
C31 C34 1.377(10) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34 0.9500 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 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 C15 C23 Br7 1.2(8) . . . . ?
Br1 C15 C23 C12 178.9(5) . . . . ?
Br5 C12 C23 Br7 2.2(8) . . . . ?
Br5 C12 C23 C15 -175.5(5) . . . . ?
Br5 C12 C27 C11 176.9(5) . . . . ?
O3 C1 C32 C13 50.6(6) . . . . ?
O3 C1 C32 C22 -72.8(5) . . . . ?
O3 C1 C32 C28 167.0(4) . . . . ?
O4 C10 C20 N1 75.6(6) . . . . ?
O4 C10 C28 C32 -23.5(5) . . . . ?
O4 C10 C29 Br2 -174.1(4) . . . . ?
O4 C13 C32 C1 145.1(4) . . . . ?
O4 C13 C32 C22 -93.8(5) . . . . ?
O4 C13 C32 C28 24.0(5) . . . . ?
O5 C1 C32 C13 -131.8(6) . . . . ?
O5 C1 C32 C22 104.8(6) . . . . ?
O5 C1 C32 C28 -15.4(8) . . . . ?
N1 C7 C11 C13 7.5(9) . . . . ?
N1 C7 C11 C27 -175.6(6) . . . . ?
N1 C7 C15 Br1 -2.2(8) . . . . ?
N1 C7 C15 C23 177.1(6) . . . . ?
C7 N1 C20 C10 -75.1(7) . . . . ?
C7 C11 C13 O4 -65.0(7) . . . . ?
C7 C11 C13 C32 54.8(8) . . . . ?
C7 C11 C27 C12 -2.6(10) . . . . ?
C7 C15 C23 Br7 -178.0(5) . . . . ?
C7 C15 C23 C12 -0.4(10) . . . . ?
C10 O4 C13 C11 86.7(5) . . . . ?
C10 O4 C13 C32 -40.6(5) . . . . ?
C10 C28 C32 C1 -122.2(5) . . . . ?
C10 C28 C32 C13 -0.1(5) . . . . ?
C10 C28 C32 C22 118.9(5) . . . . ?
C11 C7 C15 Br1 173.8(5) . . . . ?
C11 C7 C15 C23 -6.9(9) . . . . ?
C11 C13 C32 C1 20.6(6) . . . . ?
C11 C13 C32 C22 141.8(5) . . . . ?
C11 C13 C32 C28 -100.5(5) . . . . ?
C13 O4 C10 C20 -81.1(5) . . . . ?
C13 O4 C10 C28 40.8(5) . . . . ?
C13 O4 C10 C29 160.3(4) . . . . ?
C13 C11 C27 C12 174.5(6) . . . . ?
C14 C22 C25 C40 1.4(10) . . . . ?
C14 C22 C32 C1 161.9(5) . . . . ?
C14 C22 C32 C13 37.5(7) . . . . ?
C14 C22 C32 C28 -76.5(6) . . . . ?
C14 C35 C36 C40 1.9(11) . . . . ?
C15 C7 C11 C13 -168.6(6) . . . . ?
C15 C7 C11 C27 8.4(9) . . . . ?
C20 N1 C7 C11 49.1(8) . . . . ?
C20 N1 C7 C15 -135.0(6) . . . . ?
C20 C10 C28 C32 96.0(5) . . . . ?
C20 C10 C29 Br2 68.4(6) . . . . ?
C22 C14 C35 C36 -1.4(10) . . . . ?
C22 C25 C40 C36 -1.0(11) . . . . ?
C23 C12 C27 C11 -4.8(10) . . . . ?
C25 C22 C32 C1 -24.6(8) . . . . ?
C25 C22 C32 C13 -149.0(6) . . . . ?
C25 C22 C32 C28 97.0(7) . . . . ?
C27 C11 C13 O4 118.0(6) . . . . ?
C27 C11 C13 C32 -122.1(6) . . . . ?
C27 C12 C23 Br7 -176.0(5) . . . . ?
C27 C12 C23 C15 6.3(10) . . . . ?
C28 C10 C20 N1 -40.6(6) . . . . ?
C28 C10 C29 Br2 -61.8(6) . . . . ?
C29 C10 C20 N1 -171.3(5) . . . . ?
C29 C10 C28 C32 -134.9(4) . . . . ?
C32 C22 C25 C40 -172.2(6) . . . . ?
C35 C14 C22 C25 -0.3(9) . . . . ?
C35 C14 C22 C32 173.4(5) . . . . ?
C35 C36 C40 C25 -0.7(11) . . . . ?
C38 O3 C1 O5 5.4(8) . . . . ?
C38 O3 C1 C32 -176.9(5) . . . . ?
Br6 C4 C6 Br8 1.8(8) . . . . ?
Br6 C4 C6 C24 -177.6(5) . . . . ?
Br6 C4 C16 Br4 -7.8(8) . . . . ?
Br6 C4 C16 C9 175.9(5) . . . . ?
Br8 C6 C24 C8 -177.3(4) . . . . ?
O1 C2 C3 C5 57.8(6) . . . . ?
O1 C2 C3 C21 -64.1(5) . . . . ?
O1 C2 C3 C37 172.4(4) . . . . ?
O2 C5 C8 C9 -57.2(7) . . . . ?
O2 C5 C8 C24 125.2(5) . . . . ?
O2 C17 C19 N2 73.0(6) . . . . ?
O2 C17 C33 Br3 -63.5(6) . . . . ?
O2 C17 C37 C3 -17.5(5) . . . . ?
O6 C2 C3 C5 -123.9(6) . . . . ?
O6 C2 C3 C21 114.2(6) . . . . ?
O6 C2 C3 C37 -9.3(8) . . . . ?
N2 C9 C16 Br4 9.1(8) . . . . ?
N2 C9 C16 C4 -174.5(6) . . . . ?
C2 C3 C5 O2 145.8(4) . . . . ?
C2 C3 C5 C8 21.8(6) . . . . ?
C2 C3 C21 C26 -26.7(7) . . . . ?
C2 C3 C21 C30 156.6(5) . . . . ?
C2 C3 C37 C17 -124.5(5) . . . . ?
C3 C5 C8 C9 62.8(7) . . . . ?
C3 C5 C8 C24 -114.8(5) . . . . ?
C3 C21 C26 C18 -178.6(5) . . . . ?
C3 C21 C30 C31 178.3(5) . . . . ?
C4 C6 C24 C8 2.2(10) . . . . ?
C5 O2 C17 C19 -84.9(5) . . . . ?
C5 O2 C17 C33 160.6(4) . . . . ?
C5 O2 C17 C37 35.7(5) . . . . ?
C5 C3 C21 C26 -149.3(5) . . . . ?
C5 C3 C21 C30 34.0(7) . . . . ?
C5 C3 C37 C17 -4.7(5) . . . . ?
C5 C8 C9 N2 -0.1(9) . . . . ?
C5 C8 C9 C16 -175.7(5) . . . . ?
C5 C8 C24 C6 174.2(5) . . . . ?
C6 C4 C16 Br4 173.9(5) . . . . ?
C6 C4 C16 C9 -2.4(10) . . . . ?
C8 C9 C16 Br4 -175.3(4) . . . . ?
C8 C9 C16 C4 1.1(9) . . . . ?
C9 N2 C19 C17 -70.8(7) . . . . ?
C9 C8 C24 C6 -3.5(9) . . . . ?
C16 C4 C6 Br8 -179.8(5) . . . . ?
C16 C4 C6 C24 0.8(10) . . . . ?
C17 O2 C5 C3 -38.7(5) . . . . ?
C17 O2 C5 C8 87.8(5) . . . . ?
C19 N2 C9 C8 51.1(8) . . . . ?
C19 N2 C9 C16 -133.5(6) . . . . ?
C19 C17 C33 Br3 179.8(4) . . . . ?
C19 C17 C37 C3 101.0(5) . . . . ?
C21 C3 C5 O2 -93.0(5) . . . . ?
C21 C3 C5 C8 142.9(4) . . . . ?
C21 C3 C37 C17 113.3(5) . . . . ?
C21 C30 C31 C34 -0.6(10) . . . . ?
C24 C8 C9 N2 177.4(5) . . . . ?
C24 C8 C9 C16 1.8(8) . . . . ?
C26 C18 C34 C31 -0.3(10) . . . . ?
C26 C21 C30 C31 1.4(9) . . . . ?
C30 C21 C26 C18 -1.7(10) . . . . ?
C30 C31 C34 C18 0.0(11) . . . . ?
C33 C17 C19 N2 -171.0(5) . . . . ?
C33 C17 C37 C3 -137.2(5) . . . . ?
C34 C18 C26 C21 1.2(10) . . . . ?
C37 C3 C5 O2 25.6(5) . . . . ?
C37 C3 C5 C8 -98.5(5) . . . . ?
C37 C3 C21 C26 97.4(6) . . . . ?
C37 C3 C21 C30 -79.3(6) . . . . ?
C37 C17 C19 N2 -43.4(6) . . . . ?
C37 C17 C33 Br3 54.6(6) . . . . ?
C39 O1 C2 O6 2.1(8) . . . . ?
C39 O1 C2 C3 -179.5(5) . . . . ?
