#------------------------------------------------------------------------------
#$Date: 2022-03-02 03:39:21 +0200 (Wed, 02 Mar 2022) $
#$Revision: 273200 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/85/7158542.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_7158542
loop_
_publ_author_name
'Yi, Zi-Juan'
'Sun, Jian-Ting'
'Yang, Tian-Yu'
'Yu, Xian-Yong'
'Han, Xiao-Li'
'Wei, Bang-Guo'
_publ_section_title
;
 Cu(OTf)2-catalyzed C3 aza-Friedel--Crafts alkylation of indoles with
 N,O-acetals
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D1OB02383G
_journal_year                    2022
_chemical_formula_sum            'C20 H21 Br N2 O'
_chemical_formula_weight         385.30
_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
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2021-10-26 deposited with the CCDC.	2022-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                91.317(2)
_cell_angle_beta                 95.348(2)
_cell_angle_gamma                108.325(2)
_cell_formula_units_Z            4
_cell_length_a                   9.7774(6)
_cell_length_b                   10.6374(7)
_cell_length_c                   18.9895(14)
_cell_measurement_reflns_used    7988
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      48.718
_cell_measurement_theta_min      4.473
_cell_volume                     1863.8(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            36864
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.342
_exptl_absorpt_coefficient_mu    2.214
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         7312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0452
_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)+(0.0453P)²+1.4689P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1174
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4819
_reflns_number_total             7312
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob02383g2.cif
_cod_data_source_block           mo_dd21044_0m
_cod_database_code               7158542
_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   0.718
_shelx_estimated_absorpt_t_max   0.809
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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 1.07397(4) 0.27590(5) 0.08173(2) 0.06052(15) Uani 1 1 d . . . . .
O1 O 0.7150(2) 0.4573(2) 0.36155(12) 0.0387(5) Uani 1 1 d . . . . .
N1 N 0.6313(3) 0.0009(3) 0.27187(17) 0.0470(8) Uani 1 1 d . . . . .
N2 N 0.9260(3) 0.4211(2) 0.34615(14) 0.0321(6) Uani 1 1 d . . . . .
H2 H 1.0109 0.4521 0.3311 0.038 Uiso 1 1 calc R U . . .
C1 C 0.7217(4) 0.0506(3) 0.22102(19) 0.0415(8) Uani 1 1 d . . . . .
C2 C 0.7171(4) 0.0023(4) 0.1521(2) 0.0541(10) Uani 1 1 d . . . . .
H2A H 0.6434 -0.0747 0.1335 0.065 Uiso 1 1 calc R U . . .
C3 C 0.8226(4) 0.0698(4) 0.1120(2) 0.0521(10) Uani 1 1 d . . . . .
H3 H 0.8218 0.0392 0.0650 0.063 Uiso 1 1 calc R U . . .
C4 C 0.9322(4) 0.1845(4) 0.14051(18) 0.0428(8) Uani 1 1 d . . . . .
C5 C 0.9394(3) 0.2331(3) 0.20854(17) 0.0371(8) Uani 1 1 d . . . . .
H5 H 1.0140 0.3101 0.2264 0.044 Uiso 1 1 calc R U . . .
C6 C 0.8325(3) 0.1652(3) 0.25110(17) 0.0350(8) Uani 1 1 d . . . . .
C7 C 0.8044(3) 0.1839(3) 0.32261(17) 0.0350(8) Uani 1 1 d . . . . .
C8 C 0.6824(4) 0.0814(3) 0.3322(2) 0.0432(9) Uani 1 1 d . . . . .
H8 H 0.6393 0.0681 0.3748 0.052 Uiso 1 1 calc R U . . .
C9 C 0.5128(4) -0.1252(4) 0.2645(2) 0.0648(12) Uani 1 1 d . . . . .
H9A H 0.4555 -0.1316 0.2193 0.097 Uiso 1 1 calc R U . . .
H9B H 0.4520 -0.1294 0.3025 0.097 Uiso 1 1 calc R U . . .
H9C H 0.5525 -0.1980 0.2669 0.097 Uiso 1 1 calc R U . . .
C10 C 0.8874(3) 0.2918(3) 0.37754(17) 0.0335(7) Uani 1 1 d . . . . .
H10 H 0.8219 0.2938 0.4140 0.040 Uiso 1 1 calc R U . . .
C11 C 1.0251(4) 0.2728(3) 0.41575(18) 0.0415(8) Uani 1 1 d . . . . .
H11 H 1.0960 0.2805 0.3808 0.050 Uiso 1 1 calc R U . . .
C12 C 0.9942(5) 0.1372(4) 0.4462(2) 0.0652(12) Uani 1 1 d . . . . .
H12A H 0.9158 0.1230 0.4759 0.098 Uiso 1 1 calc R U . . .
H12B H 1.0804 0.1325 0.4742 0.098 Uiso 1 1 calc R U . . .
H12C H 0.9666 0.0693 0.4078 0.098 Uiso 1 1 calc R U . . .
C13 C 1.0935(4) 0.3789(4) 0.4750(2) 0.0514(10) Uani 1 1 d . . . . .
H13A H 1.1165 0.4659 0.4556 0.077 Uiso 1 1 calc R U . . .
H13B H 1.1814 0.3663 0.4970 0.077 Uiso 1 1 calc R U . . .
H13C H 1.0260 0.3724 0.5101 0.077 Uiso 1 1 calc R U . . .
C14 C 0.8361(3) 0.4936(3) 0.33966(16) 0.0303(7) Uani 1 1 d . . . . .
C15 C 0.8907(3) 0.6232(3) 0.30580(17) 0.0322(7) Uani 1 1 d . . . . .
C16 C 0.9842(4) 0.6439(3) 0.25385(19) 0.0432(9) Uani 1 1 d . . . . .
H16 H 1.0172 0.5748 0.2387 0.052 Uiso 1 1 calc R U . . .
C17 C 1.0297(4) 0.7657(4) 0.2238(2) 0.0536(10) Uani 1 1 d . . . . .
H17 H 1.0936 0.7792 0.1887 0.064 Uiso 1 1 calc R U . . .
C18 C 0.9816(5) 0.8661(4) 0.2455(2) 0.0606(11) Uani 1 1 d . . . . .
H18 H 1.0119 0.9488 0.2251 0.073 Uiso 1 1 calc R U . . .
C19 C 0.8890(5) 0.8460(4) 0.2970(2) 0.0624(12) Uani 1 1 d . . . . .
H19 H 0.8569 0.9157 0.3121 0.075 Uiso 1 1 calc R U . . .
C20 C 0.8425(4) 0.7259(4) 0.3270(2) 0.0497(9) Uani 1 1 d . . . . .
H20 H 0.7778 0.7133 0.3618 0.060 Uiso 1 1 calc R U . . .
Br2 Br 0.26397(5) 0.78908(5) 0.06225(2) 0.06973(16) Uani 1 1 d . . . . .
O2 O 0.2150(2) 0.4837(2) 0.28891(13) 0.0460(6) Uani 1 1 d . . . . .
N3 N 0.6944(3) 0.4979(3) 0.11073(16) 0.0462(8) Uani 1 1 d . . . . .
N4 N 0.4382(3) 0.4609(3) 0.29553(14) 0.0345(6) Uani 1 1 d . . . . .
H4 H 0.5232 0.4816 0.3195 0.041 Uiso 1 1 calc R U . . .
C21 C 0.6074(4) 0.5732(4) 0.09152(18) 0.0423(9) Uani 1 1 d . . . . .
C22 C 0.6192(4) 0.6663(4) 0.0399(2) 0.0526(10) Uani 1 1 d . . . . .
H22 H 0.6964 0.6866 0.0117 0.063 Uiso 1 1 calc R U . . .
C23 C 0.5157(4) 0.7267(4) 0.0318(2) 0.0534(10) Uani 1 1 d . . . . .
H23 H 0.5201 0.7893 -0.0028 0.064 Uiso 1 1 calc R U . . .
C24 C 0.4021(4) 0.6959(4) 0.07506(19) 0.0473(9) Uani 1 1 d . . . . .
C25 C 0.3854(4) 0.6030(3) 0.12473(17) 0.0392(8) Uani 1 1 d . . . . .
H25 H 0.3066 0.5828 0.1520 0.047 Uiso 1 1 calc R U . . .
C26 C 0.4905(3) 0.5390(3) 0.13344(17) 0.0364(8) Uani 1 1 d . . . . .
C27 C 0.5088(3) 0.4375(3) 0.17817(17) 0.0354(8) Uani 1 1 d . . . . .
C28 C 0.6352(4) 0.4171(4) 0.16244(18) 0.0416(8) Uani 1 1 d . . . . .
H28 H 0.6752 0.3562 0.1842 0.050 Uiso 1 1 calc R U . . .
C29 C 0.8266(4) 0.5022(5) 0.0793(2) 0.0622(12) Uani 1 1 d . . . . .
H29A H 0.8042 0.4826 0.0286 0.093 Uiso 1 1 calc R U . . .
H29B H 0.8661 0.4369 0.1001 0.093 Uiso 1 1 calc R U . . .
H29C H 0.8971 0.5899 0.0883 0.093 Uiso 1 1 calc R U . . .
C30 C 0.4098(3) 0.3719(3) 0.23166(16) 0.0327(7) Uani 1 1 d . . . . .
H30 H 0.3097 0.3606 0.2110 0.039 Uiso 1 1 calc R U . . .
C31 C 0.4159(4) 0.2332(3) 0.24987(18) 0.0419(8) Uani 1 1 d . . . . .
H31 H 0.5176 0.2405 0.2656 0.050 Uiso 1 1 calc R U . . .
C32 C 0.3653(4) 0.1384(4) 0.1843(2) 0.0572(11) Uani 1 1 d . . . . .
H32A H 0.2668 0.1326 0.1671 0.086 Uiso 1 1 calc R U . . .
H32B H 0.3685 0.0512 0.1964 0.086 Uiso 1 1 calc R U . . .
H32C H 0.4285 0.1710 0.1477 0.086 Uiso 1 1 calc R U . . .
C33 C 0.3241(5) 0.1782(4) 0.3089(2) 0.0604(11) Uani 1 1 d . . . . .
H33A H 0.3600 0.2364 0.3513 0.091 Uiso 1 1 calc R U . . .
H33B H 0.3293 0.0906 0.3186 0.091 Uiso 1 1 calc R U . . .
H33C H 0.2243 0.1724 0.2947 0.091 Uiso 1 1 calc R U . . .
C34 C 0.3405(3) 0.5120(3) 0.31888(17) 0.0343(7) Uani 1 1 d . . . . .
C35 C 0.3875(3) 0.6082(3) 0.38186(17) 0.0337(7) Uani 1 1 d . . . . .
C36 C 0.5052(4) 0.6165(4) 0.43035(19) 0.0510(10) Uani 1 1 d . . . . .
H36 H 0.5595 0.5587 0.4249 0.061 Uiso 1 1 calc R U . . .
C37 C 0.5432(5) 0.7094(5) 0.4867(2) 0.0748(14) Uani 1 1 d . . . . .
H37 H 0.6223 0.7136 0.5199 0.090 Uiso 1 1 calc R U . . .
C38 C 0.4651(5) 0.7961(5) 0.4945(3) 0.0775(14) Uani 1 1 d . . . . .
H38 H 0.4931 0.8606 0.5323 0.093 Uiso 1 1 calc R U . . .
C39 C 0.3472(4) 0.7889(4) 0.4473(2) 0.0566(11) Uani 1 1 d . . . . .
H39 H 0.2937 0.8474 0.4530 0.068 Uiso 1 1 calc R U . . .
C40 C 0.3081(4) 0.6947(4) 0.3914(2) 0.0472(9) Uani 1 1 d . . . . .
H40 H 0.2267 0.6888 0.3594 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 0.0033 0.0016 '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 -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C8 N1 C1 107.9(3) . . ?
C8 N1 C9 126.7(3) . . ?
C1 N1 C9 125.1(3) . . ?
C14 N2 C10 122.8(3) . . ?
C14 N2 H2 118.6 . . ?
C10 N2 H2 118.6 . . ?
N1 C1 C2 129.5(3) . . ?
N1 C1 C6 108.1(3) . . ?
C2 C1 C6 122.4(3) . . ?
C3 C2 C1 118.2(4) . . ?
C3 C2 H2A 120.9 . . ?
C1 C2 H2A 120.9 . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 122.5(3) . . ?
C5 C4 Br1 119.1(3) . . ?
C3 C4 Br1 118.4(3) . . ?
C4 C5 C6 118.4(3) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 118.3(3) . . ?
C5 C6 C7 134.7(3) . . ?
C1 C6 C7 107.1(3) . . ?
C8 C7 C6 105.6(3) . . ?
C8 C7 C10 125.5(3) . . ?
C6 C7 C10 128.9(3) . . ?
N1 C8 C7 111.4(3) . . ?
N1 C8 H8 124.3 . . ?
C7 C8 H8 124.3 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C7 110.4(3) . . ?
N2 C10 C11 109.1(3) . . ?
C7 C10 C11 115.1(3) . . ?
N2 C10 H10 107.3 . . ?
C7 C10 H10 107.3 . . ?
C11 C10 H10 107.3 . . ?
C12 C11 C13 109.0(3) . . ?
C12 C11 C10 111.8(3) . . ?
C13 C11 C10 111.3(3) . . ?
C12 C11 H11 108.2 . . ?
C13 C11 H11 108.2 . . ?
C10 C11 H11 108.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C14 N2 122.2(3) . . ?
O1 C14 C15 121.3(3) . . ?
N2 C14 C15 116.5(3) . . ?
C16 C15 C20 118.8(3) . . ?
C16 C15 C14 123.1(3) . . ?
C20 C15 C14 118.0(3) . . ?
C15 C16 C17 120.5(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 119.9(4) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 119.8(4) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C20 121.0(4) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C15 119.9(4) . . ?
C19 C20 H20 120.0 . . ?
C15 C20 H20 120.0 . . ?
C28 N3 C21 108.8(3) . . ?
C28 N3 C29 126.1(3) . . ?
C21 N3 C29 125.0(3) . . ?
C34 N4 C30 123.7(3) . . ?
C34 N4 H4 118.1 . . ?
C30 N4 H4 118.1 . . ?
N3 C21 C22 130.4(3) . . ?
N3 C21 C26 107.7(3) . . ?
C22 C21 C26 121.9(3) . . ?
C23 C22 C21 118.0(3) . . ?
C23 C22 H22 121.0 . . ?
C21 C22 H22 121.0 . . ?
C22 C23 C24 120.0(4) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 123.4(4) . . ?
C25 C24 Br2 119.1(3) . . ?
C23 C24 Br2 117.5(3) . . ?
C24 C25 C26 117.3(3) . . ?
C24 C25 H25 121.4 . . ?
C26 C25 H25 121.4 . . ?
C25 C26 C21 119.3(3) . . ?
C25 C26 C27 133.4(3) . . ?
C21 C26 C27 107.3(3) . . ?
C28 C27 C26 105.8(3) . . ?
C28 C27 C30 128.5(3) . . ?
C26 C27 C30 125.7(3) . . ?
N3 C28 C27 110.4(3) . . ?
N3 C28 H28 124.8 . . ?
C27 C28 H28 124.8 . . ?
N3 C29 H29A 109.5 . . ?
N3 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N3 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N4 C30 C27 109.4(3) . . ?
N4 C30 C31 111.5(3) . . ?
C27 C30 C31 114.4(3) . . ?
N4 C30 H30 107.0 . . ?
C27 C30 H30 107.0 . . ?
C31 C30 H30 107.0 . . ?
C33 C31 C32 109.8(3) . . ?
C33 C31 C30 111.6(3) . . ?
C32 C31 C30 110.1(3) . . ?
C33 C31 H31 108.4 . . ?
C32 C31 H31 108.4 . . ?
C30 C31 H31 108.4 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O2 C34 N4 122.0(3) . . ?
O2 C34 C35 120.0(3) . . ?
N4 C34 C35 117.9(3) . . ?
C36 C35 C40 118.7(3) . . ?
C36 C35 C34 123.6(3) . . ?
C40 C35 C34 117.7(3) . . ?
C37 C36 C35 120.3(3) . . ?
C37 C36 H36 119.9 . . ?
C35 C36 H36 119.9 . . ?
C36 C37 C38 120.2(4) . . ?
C36 C37 H37 119.9 . . ?
C38 C37 H37 119.9 . . ?
C39 C38 C37 120.5(4) . . ?
C39 C38 H38 119.7 . . ?
C37 C38 H38 119.7 . . ?
C38 C39 C40 119.2(4) . . ?
C38 C39 H39 120.4 . . ?
C40 C39 H39 120.4 . . ?
C39 C40 C35 121.0(4) . . ?
C39 C40 H40 119.5 . . ?
C35 C40 H40 119.5 . . ?
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 C4 1.898(3) . ?
O1 C14 1.239(3) . ?
N1 C8 1.369(5) . ?
N1 C1 1.372(4) . ?
N1 C9 1.464(4) . ?
N2 C14 1.339(4) . ?
N2 C10 1.464(4) . ?
N2 H2 0.8700 . ?
C1 C2 1.387(5) . ?
C1 C6 1.417(5) . ?
C2 C3 1.366(5) . ?
C2 H2A 0.9400 . ?
C3 C4 1.404(5) . ?
C3 H3 0.9400 . ?
C4 C5 1.368(5) . ?
C5 C6 1.406(4) . ?
C5 H5 0.9400 . ?
C6 C7 1.432(4) . ?
C7 C8 1.370(5) . ?
C7 C10 1.505(5) . ?
C8 H8 0.9400 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 C11 1.541(4) . ?
C10 H10 0.9900 . ?
C11 C12 1.517(5) . ?
C11 C13 1.522(5) . ?
C11 H11 0.9900 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C14 C15 1.497(4) . ?
C15 C16 1.381(4) . ?
C15 C20 1.385(4) . ?
C16 C17 1.386(5) . ?
C16 H16 0.9400 . ?
C17 C18 1.365(5) . ?
C17 H17 0.9400 . ?
C18 C19 1.370(6) . ?
C18 H18 0.9400 . ?
C19 C20 1.370(5) . ?
C19 H19 0.9400 . ?
C20 H20 0.9400 . ?
Br2 C24 1.913(4) . ?
O2 C34 1.245(4) . ?
N3 C28 1.368(4) . ?
N3 C21 1.371(5) . ?
N3 C29 1.462(4) . ?
N4 C34 1.341(4) . ?
N4 C30 1.471(4) . ?
N4 H4 0.8700 . ?
C21 C22 1.396(5) . ?
C21 C26 1.412(4) . ?
C22 C23 1.359(5) . ?
C22 H22 0.9400 . ?
C23 C24 1.402(5) . ?
C23 H23 0.9400 . ?
C24 C25 1.364(5) . ?
C25 C26 1.400(4) . ?
C25 H25 0.9400 . ?
C26 C27 1.433(5) . ?
C27 C28 1.378(4) . ?
C27 C30 1.499(4) . ?
C28 H28 0.9400 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 H29C 0.9700 . ?
C30 C31 1.541(4) . ?
C30 H30 0.9900 . ?
C31 C33 1.514(5) . ?
C31 C32 1.525(5) . ?
C31 H31 0.9900 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 H32C 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 H33C 0.9700 . ?
C34 C35 1.495(5) . ?
C35 C36 1.384(5) . ?
C35 C40 1.397(4) . ?
C36 C37 1.381(5) . ?
C36 H36 0.9400 . ?
C37 C38 1.383(6) . ?
C37 H37 0.9400 . ?
C38 C39 1.373(6) . ?
C38 H38 0.9400 . ?
C39 C40 1.383(5) . ?
C39 H39 0.9400 . ?
C40 H40 0.9400 . ?
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
C30 H30 Br1 0.99 3.11 3.994(3) 149.0 1_455
C29 H29B Br1 0.97 3.08 3.910(4) 144.6 .
C22 H22 Br1 0.94 2.93 3.862(4) 174.6 2_765
N4 H4 O1 0.87 2.06 2.886(3) 157.7 .
C5 H5 O2 0.94 2.42 3.351(4) 169.7 1_655
N2 H2 O2 0.87 2.15 3.006(3) 167.4 1_655
N2 H2 O2 0.87 2.15 3.006(3) 167.4 1_655
C5 H5 O2 0.94 2.42 3.351(4) 169.7 1_655
N4 H4 O1 0.87 2.06 2.886(3) 157.7 .
C22 H22 Br1 0.94 2.93 3.862(4) 174.6 2_765
C29 H29B Br1 0.97 3.08 3.910(4) 144.6 .
C30 H30 Br1 0.99 3.11 3.994(3) 149.0 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
C8 N1 C1 C2 178.3(4) . . . . ?
C9 N1 C1 C2 5.3(6) . . . . ?
C8 N1 C1 C6 0.3(4) . . . . ?
C9 N1 C1 C6 -172.7(3) . . . . ?
N1 C1 C2 C3 -178.9(4) . . . . ?
C6 C1 C2 C3 -1.0(6) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C2 C3 C4 C5 0.5(6) . . . . ?
C2 C3 C4 Br1 -178.9(3) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
Br1 C4 C5 C6 179.2(2) . . . . ?
C4 C5 C6 C1 -0.7(5) . . . . ?
C4 C5 C6 C7 179.6(3) . . . . ?
N1 C1 C6 C5 179.6(3) . . . . ?
C2 C1 C6 C5 1.4(5) . . . . ?
N1 C1 C6 C7 -0.7(4) . . . . ?
C2 C1 C6 C7 -178.9(3) . . . . ?
C5 C6 C7 C8 -179.5(3) . . . . ?
C1 C6 C7 C8 0.8(4) . . . . ?
C5 C6 C7 C10 0.7(6) . . . . ?
C1 C6 C7 C10 -179.0(3) . . . . ?
C1 N1 C8 C7 0.2(4) . . . . ?
C9 N1 C8 C7 173.1(3) . . . . ?
C6 C7 C8 N1 -0.6(4) . . . . ?
C10 C7 C8 N1 179.1(3) . . . . ?
C14 N2 C10 C7 85.1(3) . . . . ?
C14 N2 C10 C11 -147.6(3) . . . . ?
C8 C7 C10 N2 -136.0(3) . . . . ?
C6 C7 C10 N2 43.7(4) . . . . ?
C8 C7 C10 C11 100.1(4) . . . . ?
C6 C7 C10 C11 -80.3(4) . . . . ?
N2 C10 C11 C12 -176.9(3) . . . . ?
C7 C10 C11 C12 -52.2(4) . . . . ?
N2 C10 C11 C13 60.9(3) . . . . ?
C7 C10 C11 C13 -174.5(3) . . . . ?
C10 N2 C14 O1 1.9(5) . . . . ?
C10 N2 C14 C15 -179.4(3) . . . . ?
O1 C14 C15 C16 -149.3(3) . . . . ?
N2 C14 C15 C16 32.0(4) . . . . ?
O1 C14 C15 C20 29.4(4) . . . . ?
N2 C14 C15 C20 -149.3(3) . . . . ?
C20 C15 C16 C17 0.5(5) . . . . ?
C14 C15 C16 C17 179.2(3) . . . . ?
C15 C16 C17 C18 -0.2(6) . . . . ?
C16 C17 C18 C19 0.3(6) . . . . ?
C17 C18 C19 C20 -0.6(7) . . . . ?
C18 C19 C20 C15 0.9(6) . . . . ?
C16 C15 C20 C19 -0.8(5) . . . . ?
C14 C15 C20 C19 -179.6(3) . . . . ?
C28 N3 C21 C22 -177.7(4) . . . . ?
C29 N3 C21 C22 0.9(6) . . . . ?
C28 N3 C21 C26 0.7(4) . . . . ?
C29 N3 C21 C26 179.3(3) . . . . ?
N3 C21 C22 C23 179.7(4) . . . . ?
C26 C21 C22 C23 1.5(5) . . . . ?
C21 C22 C23 C24 0.6(6) . . . . ?
C22 C23 C24 C25 -2.3(6) . . . . ?
C22 C23 C24 Br2 178.2(3) . . . . ?
C23 C24 C25 C26 1.8(5) . . . . ?
Br2 C24 C25 C26 -178.7(2) . . . . ?
C24 C25 C26 C21 0.4(5) . . . . ?
C24 C25 C26 C27 -179.0(4) . . . . ?
N3 C21 C26 C25 179.4(3) . . . . ?
C22 C21 C26 C25 -2.0(5) . . . . ?
N3 C21 C26 C27 -1.1(4) . . . . ?
C22 C21 C26 C27 177.5(3) . . . . ?
C25 C26 C27 C28 -179.5(4) . . . . ?
C21 C26 C27 C28 1.0(4) . . . . ?
C25 C26 C27 C30 -0.8(6) . . . . ?
C21 C26 C27 C30 179.8(3) . . . . ?
C21 N3 C28 C27 0.0(4) . . . . ?
C29 N3 C28 C27 -178.6(3) . . . . ?
C26 C27 C28 N3 -0.7(4) . . . . ?
C30 C27 C28 N3 -179.3(3) . . . . ?
C34 N4 C30 C27 116.6(3) . . . . ?
C34 N4 C30 C31 -115.9(3) . . . . ?
C28 C27 C30 N4 100.6(4) . . . . ?
C26 C27 C30 N4 -77.9(4) . . . . ?
C28 C27 C30 C31 -25.4(5) . . . . ?
C26 C27 C30 C31 156.2(3) . . . . ?
N4 C30 C31 C33 49.9(4) . . . . ?
C27 C30 C31 C33 174.7(3) . . . . ?
N4 C30 C31 C32 172.1(3) . . . . ?
C27 C30 C31 C32 -63.1(4) . . . . ?
C30 N4 C34 O2 2.5(5) . . . . ?
C30 N4 C34 C35 -176.0(3) . . . . ?
O2 C34 C35 C36 160.2(3) . . . . ?
N4 C34 C35 C36 -21.3(5) . . . . ?
O2 C34 C35 C40 -20.3(4) . . . . ?
N4 C34 C35 C40 158.2(3) . . . . ?
C40 C35 C36 C37 -0.4(6) . . . . ?
C34 C35 C36 C37 179.1(4) . . . . ?
C35 C36 C37 C38 -1.0(7) . . . . ?
C36 C37 C38 C39 1.6(8) . . . . ?
C37 C38 C39 C40 -0.7(7) . . . . ?
C38 C39 C40 C35 -0.7(6) . . . . ?
C36 C35 C40 C39 1.3(5) . . . . ?
C34 C35 C40 C39 -178.2(3) . . . . ?
