#------------------------------------------------------------------------------
#$Date: 2023-07-05 02:03:06 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284790 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/33/7713374.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_7713374
loop_
_publ_author_name
'Arion, Vladimir'
'Wittmann, Christopher'
'Dömötör, Orsolya'
'Kuznetcova, Irina'
'Spengler, Gabriella'
'Reynisson, Johannes'
'Holder, Lauren'
'Miller, Gavin John'
'Enyedy, Eva A.'
'Bai, Ruoli'
'Hamel, Ernest'
_publ_section_title
;
 Indolo[2,3-e]benzazocines and indolo[2,3-f]benzazonines and their
 copper(II) complexes as microtubule destabilizing agents
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT01632C
_journal_year                    2023
_chemical_formula_moiety         'C21 H21 Br N2 O2, C18 H15 Br N2 O'
_chemical_formula_sum            'C39 H36 Br2 N4 O3'
_chemical_formula_weight         768.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2023-05-10 deposited with the CCDC.	2023-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.143(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5688(12)
_cell_length_b                   10.8490(10)
_cell_length_c                   27.689(5)
_cell_measurement_reflns_used    39441
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.61
_cell_measurement_theta_min      1.49
_cell_volume                     3431.1(8)
_computing_cell_refinement       'X-Area Recipe 1.36.0-0 (STOE, 2020)'
_computing_data_collection       'X-Area Pilatus3_SV 1.31.170.0 (STOE, 2020)'
_computing_data_reduction
'X-Area Integrate 1.78.3.0; X-Area LANA 1.83.8.0 (STOE, 2020)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1043
_diffrn_reflns_av_unetI/netI     0.1594
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            32811
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_min         1.783
_exptl_absorpt_coefficient_mu    2.407
_exptl_absorpt_correction_T_max  0.0244
_exptl_absorpt_correction_T_min  0.0125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.777
_refine_diff_density_min         -1.160
_refine_diff_density_rms         0.146
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         6485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.907
_refine_ls_R_factor_all          0.1491
_refine_ls_R_factor_gt           0.0570
_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)+(0.0742P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1510
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3111
_reflns_number_total             6485
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt01632c2.cif
_cod_data_source_block           chwi1084
_cod_original_cell_volume        3431.1(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7713374
_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   0.197
_shelx_estimated_absorpt_t_max   0.532
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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 0.31919(6) 0.15606(6) 0.48132(3) 0.0302(2) Uani 1 1 d . . . . .
Br2 Br 0.80556(6) 1.09024(6) 0.61567(3) 0.0382(2) Uani 1 1 d . . . . .
N30 N 0.6810(4) 0.6920(4) 0.74860(19) 0.0237(13) Uani 1 1 d . . . . .
O4 O 0.5866(3) 0.4328(4) 0.73753(16) 0.0285(11) Uani 1 1 d . . . . .
N10 N 0.4530(4) 0.4999(4) 0.64928(19) 0.0224(12) Uani 1 1 d . . . . .
H10 H 0.5038 0.4965 0.6765 0.027 Uiso 1 1 calc R U . . .
C21 C 0.7187(5) 0.5265(5) 0.6029(2) 0.0225(15) Uani 1 1 d . . . . .
H21 H 0.6480 0.5727 0.5979 0.027 Uiso 1 1 calc R U . . .
O36 O 0.6905(3) 0.6220(3) 0.82973(16) 0.0263(11) Uani 1 1 d . . . . .
C30A C 0.7059(5) 0.7967(5) 0.7231(2) 0.0187(14) Uani 1 1 d . . . . .
C12 C 0.4625(5) 0.2312(5) 0.5691(2) 0.0242(16) Uani 1 1 d . . . . .
H12 H 0.5032 0.1568 0.5650 0.029 Uiso 1 1 calc R U . . .
C14 C 0.3102(5) 0.3746(5) 0.5370(2) 0.0204(15) Uani 1 1 d . . . . .
H14 H 0.2465 0.3965 0.5124 0.024 Uiso 1 1 calc R U . . .
C10A C 0.4374(5) 0.4125(5) 0.6134(2) 0.0212(15) Uani 1 1 d . . . . .
C29 C 0.6914(6) 0.4632(5) 0.7402(2) 0.0240(15) Uani 1 1 d . . . . .
O14 O 0.3134(4) 0.6725(4) 0.70688(16) 0.0318(12) Uani 1 1 d . . . . .
N28 N 0.7791(4) 0.3862(4) 0.75512(19) 0.0247(13) Uani 1 1 d . . . . .
H28 H 0.7622 0.3071 0.7543 0.030 Uiso 1 1 calc R U . . .
C14B C 0.3084(5) 0.5712(5) 0.5912(2) 0.0226(15) Uani 1 1 d . . . . .
C34C C 0.7980(5) 0.5421(5) 0.6464(2) 0.0236(15) Uani 1 1 d . . . . .
C22 C 0.7420(6) 0.4446(5) 0.5671(2) 0.0289(17) Uani 1 1 d . . . . .
H22 H 0.6868 0.4336 0.5382 0.035 Uiso 1 1 calc R U . . .
C11 C 0.4978(5) 0.3030(5) 0.6098(2) 0.0210(15) Uani 1 1 d . . . . .
H11 H 0.5607 0.2787 0.6343 0.025 Uiso 1 1 calc R U . . .
C35 C 0.6236(5) 0.6854(6) 0.7914(2) 0.0292(17) Uani 1 1 d . . . . .
H35A H 0.6086 0.7700 0.8023 0.035 Uiso 1 1 calc R U . . .
H35B H 0.5471 0.6435 0.7826 0.035 Uiso 1 1 calc R U . . .
C34B C 0.7650(5) 0.6253(5) 0.6843(2) 0.0193(14) Uani 1 1 d . . . . .
C24A C 0.9039(5) 0.4750(5) 0.6539(2) 0.0204(15) Uani 1 1 d . . . . .
C34A C 0.7562(5) 0.7576(5) 0.6822(2) 0.0191(14) Uani 1 1 d . . . . .
C13 C 0.3687(5) 0.2653(5) 0.5339(2) 0.0211(15) Uani 1 1 d . . . . .
C14A C 0.3455(5) 0.4525(5) 0.5764(2) 0.0176(14) Uani 1 1 d . . . . .
C9A C 0.3747(5) 0.5950(5) 0.6355(2) 0.0224(15) Uani 1 1 d . . . . .
N8 N 0.3966(4) 0.8074(4) 0.66004(19) 0.0273(14) Uani 1 1 d . . . . .
H8 H 0.3721 0.8690 0.6764 0.033 Uiso 1 1 calc R U . . .
C23 C 0.8451(6) 0.3797(5) 0.5738(3) 0.0298(17) Uani 1 1 d . . . . .
H23 H 0.8623 0.3246 0.5492 0.036 Uiso 1 1 calc R U . . .
C27 C 0.9006(5) 0.4197(6) 0.7727(2) 0.0262(16) Uani 1 1 d . . . . .
H27A H 0.9264 0.3759 0.8039 0.031 Uiso 1 1 calc R U . . .
H27B H 0.9036 0.5091 0.7799 0.031 Uiso 1 1 calc R U . . .
C7 C 0.4723(5) 0.8393(5) 0.6244(2) 0.0257(16) Uani 1 1 d . . . . .
H7A H 0.5142 0.7639 0.6168 0.031 Uiso 1 1 calc R U . . .
H7B H 0.5319 0.8987 0.6398 0.031 Uiso 1 1 calc R U . . .
C24 C 0.9245(5) 0.3954(5) 0.6169(3) 0.0279(17) Uani 1 1 d . . . . .
H24 H 0.9955 0.3499 0.6211 0.033 Uiso 1 1 calc R U . . .
C38 C 0.8521(5) 0.6160(6) 0.8946(2) 0.0359(18) Uani 1 1 d . . . . .
H38A H 0.8694 0.5333 0.8834 0.054 Uiso 1 1 calc R U . . .
H38B H 0.8013 0.6093 0.9197 0.054 Uiso 1 1 calc R U . . .
H38C H 0.9253 0.6571 0.9085 0.054 Uiso 1 1 calc R U . . .
C26 C 0.9875(5) 0.3923(6) 0.7387(2) 0.0279(17) Uani 1 1 d . . . . .
H26A H 0.9669 0.3121 0.7225 0.033 Uiso 1 1 calc R U . . .
H26B H 1.0663 0.3836 0.7585 0.033 Uiso 1 1 calc R U . . .
C37 C 0.7911(5) 0.6898(6) 0.8522(2) 0.0281(17) Uani 1 1 d . . . . .
H37A H 0.7669 0.7708 0.8637 0.034 Uiso 1 1 calc R U . . .
H37B H 0.8447 0.7043 0.8282 0.034 Uiso 1 1 calc R U . . .
C25 C 0.9938(5) 0.4895(6) 0.6991(2) 0.0260(16) Uani 1 1 d . . . . .
H25A H 0.9843 0.5720 0.7132 0.031 Uiso 1 1 calc R U . . .
H25B H 1.0726 0.4865 0.6895 0.031 Uiso 1 1 calc R U . . .
C29A C 0.7191(5) 0.5903(5) 0.7250(2) 0.0223(15) Uani 1 1 d . . . . .
C34 C 0.7884(5) 0.8444(5) 0.6502(2) 0.0205(14) Uani 1 1 d . . . . .
H34 H 0.8233 0.8203 0.6228 0.025 Uiso 1 1 calc R U . . .
C33 C 0.7682(5) 0.9669(6) 0.6593(2) 0.0240(15) Uani 1 1 d . . . . .
C31 C 0.6870(5) 0.9204(6) 0.7321(2) 0.0248(15) Uani 1 1 d . . . . .
H31 H 0.6520 0.9456 0.7593 0.030 Uiso 1 1 calc R U . . .
C6 C 0.4110(5) 0.8946(5) 0.5764(2) 0.0200(15) Uani 1 1 d . . . . .
H6A H 0.4698 0.9418 0.5616 0.024 Uiso 1 1 calc R U . . .
H6B H 0.3519 0.9542 0.5842 0.024 Uiso 1 1 calc R U . . .
C14C C 0.2111(5) 0.6491(5) 0.5673(2) 0.0228(15) Uani 1 1 d . . . . .
C1 C 0.0961(5) 0.6129(5) 0.5702(2) 0.0262(16) Uani 1 1 d . . . . .
H1 H 0.0824 0.5359 0.5847 0.031 Uiso 1 1 calc R U . . .
C5 C 0.3502(5) 0.8054(5) 0.5378(2) 0.0260(16) Uani 1 1 d . . . . .
H5A H 0.3429 0.8458 0.5054 0.031 Uiso 1 1 calc R U . . .
H5B H 0.4009 0.7321 0.5370 0.031 Uiso 1 1 calc R U . . .
C4A C 0.2297(5) 0.7622(5) 0.5455(2) 0.0200(15) Uani 1 1 d . . . . .
C4 C 0.1326(5) 0.8354(6) 0.5278(2) 0.0284(16) Uani 1 1 d . . . . .
H4 H 0.1444 0.9121 0.5127 0.034 Uiso 1 1 calc R U . . .
C2 C 0.0028(5) 0.6871(6) 0.5523(3) 0.0332(18) Uani 1 1 d . . . . .
H2 H -0.0746 0.6609 0.5543 0.040 Uiso 1 1 calc R U . . .
C3 C 0.0207(5) 0.7990(6) 0.5315(2) 0.0310(17) Uani 1 1 d . . . . .
H3 H -0.0439 0.8508 0.5197 0.037 Uiso 1 1 calc R U . . .
C9 C 0.3605(5) 0.6950(5) 0.6705(2) 0.0219(15) Uani 1 1 d . . . . .
C32 C 0.7208(5) 1.0048(5) 0.7001(2) 0.0256(16) Uani 1 1 d . . . . .
H32 H 0.7118 1.0903 0.7059 0.031 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
C29A N30 C30A 107.6(5) . . ?
C29A N30 C35 124.4(5) . . ?
C30A N30 C35 127.9(5) . . ?
C10A N10 C9A 108.1(5) . . ?
C10A N10 H10 125.9 . . ?
C9A N10 H10 125.9 . . ?
C22 C21 C34C 121.0(6) . . ?
C22 C21 H21 119.5 . . ?
C34C C21 H21 119.5 . . ?
C35 O36 C37 113.1(5) . . ?
C31 C30A N30 130.2(6) . . ?
C31 C30A C34A 121.9(5) . . ?
N30 C30A C34A 107.8(5) . . ?
C11 C12 C13 121.4(6) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C13 C14 C14A 119.1(6) . . ?
C13 C14 H14 120.4 . . ?
C14A C14 H14 120.4 . . ?
N10 C10A C11 129.5(6) . . ?
N10 C10A C14A 108.1(5) . . ?
C11 C10A C14A 122.4(6) . . ?
O4 C29 N28 122.6(6) . . ?
O4 C29 C29A 118.6(5) . . ?
N28 C29 C29A 118.8(5) . . ?
C29 N28 C27 126.5(5) . . ?
C29 N28 H28 116.8 . . ?
C27 N28 H28 116.8 . . ?
C9A C14B C14A 106.0(5) . . ?
C9A C14B C14C 125.1(6) . . ?
C14A C14B C14C 128.7(6) . . ?
C21 C34C C24A 119.8(6) . . ?
C21 C34C C34B 118.4(5) . . ?
C24A C34C C34B 121.8(6) . . ?
C23 C22 C21 119.7(7) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C12 C11 C10A 117.1(6) . . ?
C12 C11 H11 121.5 . . ?
C10A C11 H11 121.5 . . ?
O36 C35 N30 112.1(5) . . ?
O36 C35 H35A 109.2 . . ?
N30 C35 H35A 109.2 . . ?
O36 C35 H35B 109.2 . . ?
N30 C35 H35B 109.2 . . ?
H35A C35 H35B 107.9 . . ?
C29A C34B C34A 106.0(5) . . ?
C29A C34B C34C 126.2(5) . . ?
C34A C34B C34C 127.1(5) . . ?
C24 C24A C34C 117.3(6) . . ?
C24 C24A C25 120.2(5) . . ?
C34C C24A C25 122.5(6) . . ?
C34 C34A C30A 119.6(5) . . ?
C34 C34A C34B 132.9(6) . . ?
C30A C34A C34B 107.5(5) . . ?
C14 C13 C12 121.7(6) . . ?
C14 C13 Br1 119.7(5) . . ?
C12 C13 Br1 118.7(4) . . ?
C14 C14A C10A 118.2(5) . . ?
C14 C14A C14B 134.9(6) . . ?
C10A C14A C14B 106.9(5) . . ?
C14B C9A N10 110.9(5) . . ?
C14B C9A C9 128.5(6) . . ?
N10 C9A C9 120.0(6) . . ?
C9 N8 C7 127.2(5) . . ?
C9 N8 H8 116.4 . . ?
C7 N8 H8 116.4 . . ?
C22 C23 C24 119.5(6) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
N28 C27 C26 116.3(5) . . ?
N28 C27 H27A 108.2 . . ?
C26 C27 H27A 108.2 . . ?
N28 C27 H27B 108.2 . . ?
C26 C27 H27B 108.2 . . ?
H27A C27 H27B 107.4 . . ?
N8 C7 C6 115.8(5) . . ?
N8 C7 H7A 108.3 . . ?
C6 C7 H7A 108.3 . . ?
N8 C7 H7B 108.3 . . ?
C6 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C24A C24 C23 122.7(6) . . ?
C24A C24 H24 118.7 . . ?
C23 C24 H24 118.7 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C27 C26 C25 115.0(5) . . ?
C27 C26 H26A 108.5 . . ?
C25 C26 H26A 108.5 . . ?
C27 C26 H26B 108.5 . . ?
C25 C26 H26B 108.5 . . ?
H26A C26 H26B 107.5 . . ?
O36 C37 C38 108.2(5) . . ?
O36 C37 H37A 110.1 . . ?
C38 C37 H37A 110.1 . . ?
O36 C37 H37B 110.1 . . ?
C38 C37 H37B 110.1 . . ?
H37A C37 H37B 108.4 . . ?
C24A C25 C26 114.7(5) . . ?
C24A C25 H25A 108.6 . . ?
C26 C25 H25A 108.6 . . ?
C24A C25 H25B 108.6 . . ?
C26 C25 H25B 108.6 . . ?
H25A C25 H25B 107.6 . . ?
C34B C29A N30 111.0(5) . . ?
C34B C29A C29 128.0(5) . . ?
N30 C29A C29 120.2(5) . . ?
C33 C34 C34A 118.0(6) . . ?
C33 C34 H34 121.0 . . ?
C34A C34 H34 121.0 . . ?
C34 C33 C32 122.1(6) . . ?
C34 C33 Br2 120.1(5) . . ?
C32 C33 Br2 117.8(5) . . ?
C32 C31 C30A 117.3(6) . . ?
C32 C31 H31 121.3 . . ?
C30A C31 H31 121.3 . . ?
C7 C6 C5 117.3(5) . . ?
C7 C6 H6A 108.0 . . ?
C5 C6 H6A 108.0 . . ?
C7 C6 H6B 108.0 . . ?
C5 C6 H6B 108.0 . . ?
H6A C6 H6B 107.2 . . ?
C4A C14C C1 118.8(6) . . ?
C4A C14C C14B 122.4(5) . . ?
C1 C14C C14B 118.5(6) . . ?
C2 C1 C14C 120.9(6) . . ?
C2 C1 H1 119.6 . . ?
C14C C1 H1 119.6 . . ?
C4A C5 C6 115.4(5) . . ?
C4A C5 H5A 108.4 . . ?
C6 C5 H5A 108.4 . . ?
C4A C5 H5B 108.4 . . ?
C6 C5 H5B 108.4 . . ?
H5A C5 H5B 107.5 . . ?
C4 C4A C14C 118.6(6) . . ?
C4 C4A C5 118.6(5) . . ?
C14C C4A C5 122.6(5) . . ?
C3 C4 C4A 121.6(6) . . ?
C3 C4 H4 119.2 . . ?
C4A C4 H4 119.2 . . ?
C3 C2 C1 120.5(6) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.5(6) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
O14 C9 N8 123.3(6) . . ?
O14 C9 C9A 119.7(5) . . ?
N8 C9 C9A 117.0(6) . . ?
C31 C32 C33 121.0(6) . . ?
C31 C32 H32 119.5 . . ?
C33 C32 H32 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 C13 1.895(6) . ?
Br2 C33 1.898(6) . ?
N30 C29A 1.389(7) . ?
N30 C30A 1.392(7) . ?
N30 C35 1.450(7) . ?
O4 C29 1.248(7) . ?
N10 C10A 1.365(7) . ?
N10 C9A 1.385(7) . ?
N10 H10 0.8800 . ?
C21 C22 1.389(8) . ?
C21 C34C 1.404(8) . ?
C21 H21 0.9500 . ?
O36 C35 1.392(7) . ?
O36 C37 1.433(7) . ?
C30A C31 1.389(8) . ?
C30A C34A 1.418(8) . ?
C12 C11 1.376(8) . ?
C12 C13 1.389(8) . ?
C12 H12 0.9500 . ?
C14 C13 1.374(7) . ?
C14 C14A 1.390(8) . ?
C14 H14 0.9500 . ?
C10A C11 1.390(7) . ?
C10A C14A 1.422(8) . ?
C29 N28 1.328(7) . ?
C29 C29A 1.491(8) . ?
O14 C9 1.242(7) . ?
N28 C27 1.459(7) . ?
N28 H28 0.8800 . ?
C14B C9A 1.363(8) . ?
C14B C14A 1.438(8) . ?
C14B C14C 1.477(8) . ?
C34C C24A 1.412(8) . ?
C34C C34B 1.479(8) . ?
C22 C23 1.372(8) . ?
C22 H22 0.9500 . ?
C11 H11 0.9500 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C34B C29A 1.373(8) . ?
C34B C34A 1.440(7) . ?
C24A C24 1.390(8) . ?
C24A C25 1.502(8) . ?
C34A C34 1.383(7) . ?
C9A C9 1.483(8) . ?
N8 C9 1.335(7) . ?
N8 C7 1.462(7) . ?
N8 H8 0.8800 . ?
C23 C24 1.396(9) . ?
C23 H23 0.9500 . ?
C27 C26 1.513(8) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C7 C6 1.526(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C24 H24 0.9500 . ?
C38 C37 1.503(8) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C26 C25 1.531(8) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C34 C33 1.379(7) . ?
C34 H34 0.9500 . ?
C33 C32 1.396(8) . ?
C31 C32 1.373(8) . ?
C31 H31 0.9500 . ?
C6 C5 1.528(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C14C C4A 1.400(8) . ?
C14C C1 1.401(7) . ?
C1 C2 1.374(8) . ?
C1 H1 0.9500 . ?
C5 C4A 1.518(8) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C4A C4 1.400(8) . ?
C4 C3 1.373(8) . ?
C4 H4 0.9500 . ?
C2 C3 1.373(8) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C32 H32 0.9500 . ?
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
N10 H10 O4 0.88 1.93 2.773(7) 159.2 .
N28 H28 O14 0.88 2.09 2.826(6) 141.2 2_646
N8 H8 O4 0.88 2.45 3.124(7) 133.3 2_656
C34 H34 Br1 0.95 3.10 3.657(6) 119.3 3_666
C31 H31 O14 0.95 2.64 3.215(7) 119.3 2_656
C6 H6A Br1 0.99 3.07 3.766(6) 128.5 3_666
C32 H32 O14 0.95 2.63 3.228(8) 121.1 2_656
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
C29A N30 C30A C31 -179.0(6) . . . . ?
C35 N30 C30A C31 2.4(10) . . . . ?
C29A N30 C30A C34A 2.1(6) . . . . ?
C35 N30 C30A C34A -176.5(6) . . . . ?
C9A N10 C10A C11 177.4(6) . . . . ?
C9A N10 C10A C14A -1.1(6) . . . . ?
O4 C29 N28 C27 -161.3(6) . . . . ?
C29A C29 N28 C27 20.2(9) . . . . ?
C22 C21 C34C C24A 0.8(9) . . . . ?
C22 C21 C34C C34B -176.5(5) . . . . ?
C34C C21 C22 C23 -1.4(9) . . . . ?
C13 C12 C11 C10A -1.7(8) . . . . ?
N10 C10A C11 C12 179.7(6) . . . . ?
C14A C10A C11 C12 -2.0(9) . . . . ?
C37 O36 C35 N30 71.9(6) . . . . ?
C29A N30 C35 O36 56.1(8) . . . . ?
C30A N30 C35 O36 -125.5(6) . . . . ?
C21 C34C C34B C29A 98.5(8) . . . . ?
C24A C34C C34B C29A -78.7(8) . . . . ?
C21 C34C C34B C34A -70.5(8) . . . . ?
C24A C34C C34B C34A 112.2(7) . . . . ?
C21 C34C C24A C24 0.1(8) . . . . ?
C34B C34C C24A C24 177.3(5) . . . . ?
C21 C34C C24A C25 178.5(5) . . . . ?
C34B C34C C24A C25 -4.3(9) . . . . ?
C31 C30A C34A C34 0.4(9) . . . . ?
N30 C30A C34A C34 179.4(5) . . . . ?
C31 C30A C34A C34B 179.1(5) . . . . ?
N30 C30A C34A C34B -1.9(7) . . . . ?
C29A C34B C34A C34 179.4(6) . . . . ?
C34C C34B C34A C34 -9.8(11) . . . . ?
C29A C34B C34A C30A 0.9(7) . . . . ?
C34C C34B C34A C30A 171.7(6) . . . . ?
C14A C14 C13 C12 -0.3(9) . . . . ?
C14A C14 C13 Br1 178.3(4) . . . . ?
C11 C12 C13 C14 2.9(9) . . . . ?
C11 C12 C13 Br1 -175.8(4) . . . . ?
C13 C14 C14A C10A -3.2(8) . . . . ?
C13 C14 C14A C14B 178.7(6) . . . . ?
N10 C10A C14A C14 -176.9(5) . . . . ?
C11 C10A C14A C14 4.4(9) . . . . ?
N10 C10A C14A C14B 1.7(6) . . . . ?
C11 C10A C14A C14B -177.0(5) . . . . ?
C9A C14B C14A C14 176.6(6) . . . . ?
C14C C14B C14A C14 2.3(11) . . . . ?
C9A C14B C14A C10A -1.6(6) . . . . ?
C14C C14B C14A C10A -175.9(6) . . . . ?
C14A C14B C9A N10 1.0(7) . . . . ?
C14C C14B C9A N10 175.6(5) . . . . ?
C14A C14B C9A C9 -169.7(6) . . . . ?
C14C C14B C9A C9 4.9(10) . . . . ?
C10A N10 C9A C14B 0.0(7) . . . . ?
C10A N10 C9A C9 171.6(5) . . . . ?
C21 C22 C23 C24 1.1(9) . . . . ?
C29 N28 C27 C26 -107.5(7) . . . . ?
C9 N8 C7 C6 103.4(7) . . . . ?
C34C C24A C24 C23 -0.5(9) . . . . ?
C25 C24A C24 C23 -178.9(5) . . . . ?
C22 C23 C24 C24A -0.1(9) . . . . ?
N28 C27 C26 C25 82.8(7) . . . . ?
C35 O36 C37 C38 176.6(5) . . . . ?
C24 C24A C25 C26 -84.4(7) . . . . ?
C34C C24A C25 C26 97.3(7) . . . . ?
C27 C26 C25 C24A -84.6(7) . . . . ?
C34A C34B C29A N30 0.4(7) . . . . ?
C34C C34B C29A N30 -170.5(5) . . . . ?
C34A C34B C29A C29 170.5(6) . . . . ?
C34C C34B C29A C29 -0.5(11) . . . . ?
C30A N30 C29A C34B -1.6(7) . . . . ?
C35 N30 C29A C34B 177.1(5) . . . . ?
C30A N30 C29A C29 -172.5(5) . . . . ?
C35 N30 C29A C29 6.2(9) . . . . ?
O4 C29 C29A C34B -109.3(7) . . . . ?
N28 C29 C29A C34B 69.3(9) . . . . ?
O4 C29 C29A N30 60.0(8) . . . . ?
N28 C29 C29A N30 -121.4(6) . . . . ?
C30A C34A C34 C33 -0.9(9) . . . . ?
C34B C34A C34 C33 -179.3(6) . . . . ?
C34A C34 C33 C32 2.3(9) . . . . ?
C34A C34 C33 Br2 -178.0(4) . . . . ?
N30 C30A C31 C32 -179.9(6) . . . . ?
C34A C30A C31 C32 -1.1(9) . . . . ?
N8 C7 C6 C5 -80.2(6) . . . . ?
C9A C14B C14C C4A 74.1(9) . . . . ?
C14A C14B C14C C4A -112.6(7) . . . . ?
C9A C14B C14C C1 -100.6(8) . . . . ?
C14A C14B C14C C1 72.7(9) . . . . ?
C4A C14C C1 C2 -0.5(10) . . . . ?
C14B C14C C1 C2 174.4(6) . . . . ?
C7 C6 C5 C4A 80.7(6) . . . . ?
C1 C14C C4A C4 0.6(9) . . . . ?
C14B C14C C4A C4 -174.1(6) . . . . ?
C1 C14C C4A C5 -175.9(6) . . . . ?
C14B C14C C4A C5 9.4(9) . . . . ?
C6 C5 C4A C4 85.4(7) . . . . ?
C6 C5 C4A C14C -98.2(7) . . . . ?
C14C C4A C4 C3 0.3(10) . . . . ?
C5 C4A C4 C3 176.9(6) . . . . ?
C14C C1 C2 C3 -0.4(10) . . . . ?
C1 C2 C3 C4 1.2(10) . . . . ?
C4A C4 C3 C2 -1.2(10) . . . . ?
C7 N8 C9 O14 167.0(6) . . . . ?
C7 N8 C9 C9A -15.2(9) . . . . ?
C14B C9A C9 O14 100.7(8) . . . . ?
N10 C9A C9 O14 -69.3(8) . . . . ?
C14B C9A C9 N8 -77.2(8) . . . . ?
N10 C9A C9 N8 112.8(6) . . . . ?
C30A C31 C32 C33 2.3(9) . . . . ?
C34 C33 C32 C31 -3.0(9) . . . . ?
Br2 C33 C32 C31 177.2(4) . . . . ?
