#------------------------------------------------------------------------------
#$Date: 2023-06-09 10:21:43 +0300 (Fri, 09 Jun 2023) $
#$Revision: 284428 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/73/8107333.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_8107333
loop_
_publ_author_name
'Xiao, Zhenxiu'
'Wu, Li'
'Su, Yizi'
'Jiang, Wujiu'
_publ_section_title
;
 The crystal structure of
 (E)-2-((5-bromo-2-hydroxybenzylidene)amino)-3′,6′-bis(ethylamino)-2′,
 7′-dimethylspiro[isoindoline-1,9′-xanthen]-3-one,
 C33H31BrN4O3
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1197
_journal_page_last               1199
_journal_paper_doi               10.1515/ncrs-2022-0432
_journal_volume                  237
_journal_year                    2022
_chemical_formula_sum            'C33 H31 Br N4 O3'
_chemical_formula_weight         611.53
_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   mixed
_cell_angle_alpha                90
_cell_angle_beta                 98.4470(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3451(7)
_cell_length_b                   17.3057(13)
_cell_length_c                   18.4402(13)
_cell_measurement_reflns_used    4211
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.94
_cell_measurement_theta_min      2.35
_cell_volume                     2949.9(4)
_computing_cell_refinement       'Bruker SAINT [1]'
_computing_data_collection       'Bruker APEX2 [1]'
_computing_data_reduction        'Bruker SAINT [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXL-2018/3 [3]'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018) [3]'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018) [2]'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0255
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.622
_exptl_absorpt_coefficient_mu    1.434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       acicular
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_transmission_factor_max   0.8836
_exptl_transmission_factor_min   0.7642
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.737
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         5797
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0409
_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)+(0.0536P)²+0.5170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1106
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3968
_reflns_number_total             5797
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0432_suppl.cif
_cod_data_source_block           jwj099
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8107333
_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   0.762
_shelx_estimated_absorpt_t_max   0.847
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 0.31205(4) 0.91976(2) 1.11742(2) 0.07085(14) Uani 1 1 d . . . . .
O1 O 0.5752(2) 0.69126(10) 0.81706(10) 0.0547(5) Uani 1 1 d . . . . .
O2 O 0.2741(2) 1.06985(10) 0.82071(10) 0.0577(5) Uani 1 1 d . . . . .
H2 H 0.313358 1.043836 0.792112 0.087 Uiso 1 1 calc R U . . .
O3 O 0.3878(3) 1.00532(11) 0.63994(11) 0.0787(6) Uani 1 1 d . . . . .
N1 N 0.0904(3) 0.60231(16) 0.79538(16) 0.0815(8) Uani 1 1 d . . . . .
H1 H 0.002097 0.605472 0.774351 0.098 Uiso 1 1 calc R U . . .
N3 N 0.4413(2) 0.90494(10) 0.72138(10) 0.0389(5) Uani 1 1 d . . . . .
N4 N 0.3947(2) 0.94480(11) 0.77698(11) 0.0407(5) Uani 1 1 d . . . . .
C1 C 0.4998(2) 0.82461(12) 0.72406(12) 0.0345(5) Uani 1 1 d . . . . .
C2 C 0.6392(2) 0.81804(13) 0.77737(11) 0.0361(5) Uani 1 1 d . . . . .
C3 C 0.7439(2) 0.87569(14) 0.78466(12) 0.0429(6) Uani 1 1 d . . . . .
H3 H 0.724964 0.920649 0.757307 0.051 Uiso 1 1 calc R U . . .
C4 C 0.8738(3) 0.86982(16) 0.83013(14) 0.0517(7) Uani 1 1 d . . . . .
C5 C 0.9007(3) 0.80160(19) 0.87181(14) 0.0583(7) Uani 1 1 d . . . . .
C6 C 0.7977(3) 0.74366(17) 0.86594(13) 0.0562(7) Uani 1 1 d . . . . .
H6 H 0.814932 0.698861 0.893707 0.067 Uiso 1 1 calc R U . . .
C7 C 0.6691(3) 0.75223(14) 0.81886(12) 0.0421(6) Uani 1 1 d . . . . .
C8 C 0.4325(3) 0.70393(14) 0.78684(13) 0.0448(6) Uani 1 1 d . . . . .
C9 C 0.3348(3) 0.64854(15) 0.80387(15) 0.0565(7) Uani 1 1 d . . . . .
H9 H 0.367504 0.606577 0.833215 0.068 Uiso 1 1 calc R U . . .
C10 C 0.1895(3) 0.65577(16) 0.77727(15) 0.0582(8) Uani 1 1 d . . . . .
C11 C 0.1418(3) 0.71854(16) 0.73117(15) 0.0538(7) Uani 1 1 d . . . . .
C12 C 0.2432(3) 0.77179(15) 0.71618(13) 0.0458(6) Uani 1 1 d . . . . .
H12 H 0.211785 0.813561 0.686287 0.055 Uiso 1 1 calc R U . . .
C13 C 0.3896(2) 0.76651(13) 0.74323(12) 0.0375(5) Uani 1 1 d . . . . .
C14 C 0.5273(2) 0.81718(13) 0.64492(12) 0.0391(5) Uani 1 1 d . . . . .
C15 C 0.5844(3) 0.75520(15) 0.61209(13) 0.0504(6) Uani 1 1 d . . . . .
H15 H 0.610054 0.709890 0.637875 0.060 Uiso 1 1 calc R U . . .
C16 C 0.6022(3) 0.76300(19) 0.53896(15) 0.0666(8) Uani 1 1 d . . . . .
H16 H 0.641110 0.722053 0.515635 0.080 Uiso 1 1 calc R U . . .
C17 C 0.5642(4) 0.8293(2) 0.50021(16) 0.0827(10) Uani 1 1 d . . . . .
H17 H 0.576815 0.832538 0.451205 0.099 Uiso 1 1 calc R U . . .
C18 C 0.5077(4) 0.89073(19) 0.53323(16) 0.0787(10) Uani 1 1 d . . . . .
H18 H 0.482456 0.936016 0.507322 0.094 Uiso 1 1 calc R U . . .
C19 C 0.4888(3) 0.88390(15) 0.60630(13) 0.0516(6) Uani 1 1 d . . . . .
C20 C 0.4322(3) 0.94026(15) 0.65365(14) 0.0513(6) Uani 1 1 d . . . . .
C21 C 0.4037(3) 0.91669(15) 0.84127(14) 0.0397(5) Uani 1 1 d . . . . .
C22 C 0.3505(2) 0.96055(13) 0.89921(12) 0.0385(5) Uani 1 1 d . . . . .
C23 C 0.3570(3) 0.92774(14) 0.96815(13) 0.0428(6) Uani 1 1 d . . . . .
H23 H 0.398708 0.879237 0.977062 0.051 Uiso 1 1 calc R U . . .
C24 C 0.3024(3) 0.96589(15) 1.02368(13) 0.0484(6) Uani 1 1 d . . . . .
C25 C 0.2414(3) 1.03789(16) 1.01127(15) 0.0560(7) Uani 1 1 d . . . . .
H25 H 0.205221 1.063915 1.048795 0.067 Uiso 1 1 calc R U . . .
C26 C 0.2342(3) 1.07128(15) 0.94304(15) 0.0557(7) Uani 1 1 d . . . . .
H26 H 0.192793 1.119962 0.934924 0.067 Uiso 1 1 calc R U . . .
C27 C 0.2872(3) 1.03384(14) 0.88648(13) 0.0438(6) Uani 1 1 d . . . . .
C28 C 0.1292(4) 0.5416(2) 0.8480(2) 0.0981(13) Uani 1 1 d . . . . .
H28A H 0.179139 0.563645 0.893144 0.118 Uiso 1 1 calc R U . . .
H28B H 0.194453 0.505782 0.829151 0.118 Uiso 1 1 calc R U . . .
C29 C -0.0053(6) 0.4983(3) 0.8640(3) 0.154(2) Uani 1 1 d . . . . .
H29A H -0.068668 0.533502 0.883987 0.232 Uiso 1 1 calc R U . . .
H29B H 0.022915 0.457717 0.898631 0.232 Uiso 1 1 calc R U . . .
H29C H -0.054715 0.476473 0.819345 0.232 Uiso 1 1 calc R U . . .
C32 C -0.0150(3) 0.7267(2) 0.69822(18) 0.0793(10) Uani 1 1 d . . . . .
H32A H -0.028001 0.773915 0.670666 0.119 Uiso 1 1 calc R U . . .
H32B H -0.073949 0.727756 0.736674 0.119 Uiso 1 1 calc R U . . .
H32C H -0.042777 0.683737 0.666354 0.119 Uiso 1 1 calc R U . . .
C33 C 0.9831(3) 0.9336(2) 0.83504(19) 0.0775(10) Uani 1 1 d . . . . .
H33A H 0.943300 0.976617 0.806015 0.116 Uiso 1 1 calc R U . . .
H33B H 1.068440 0.915505 0.817057 0.116 Uiso 1 1 calc R U . . .
H33C H 1.007599 0.949429 0.885216 0.116 Uiso 1 1 calc R U . . .
N2A N 1.0306(3) 0.79465(19) 0.91838(15) 0.0913(9) Uani 0.580(10) 1 d . . P A 1
H2A H 1.097608 0.828959 0.920167 0.110 Uiso 0.580(10) 1 calc R U P A 1
C30A C 1.0480(9) 0.7206(7) 0.9675(6) 0.085(3) Uani 0.580(10) 1 d D . P A 1
H30A H 0.978192 0.721099 1.001571 0.102 Uiso 0.580(10) 1 calc R U P A 1
H30B H 1.032084 0.674635 0.937313 0.102 Uiso 0.580(10) 1 calc R U P A 1
C31A C 1.1983(9) 0.7210(5) 1.0082(5) 0.128(4) Uani 0.580(10) 1 d D . P A 1
H31A H 1.265446 0.731678 0.974808 0.192 Uiso 0.580(10) 1 calc R U P A 1
H31B H 1.219639 0.671497 1.030645 0.192 Uiso 0.580(10) 1 calc R U P A 1
H31C H 1.206410 0.760222 1.045473 0.192 Uiso 0.580(10) 1 calc R U P A 1
N2B N 1.0306(3) 0.79465(19) 0.91838(15) 0.0913(9) Uani 0.420(10) 1 d . . P A 2
H2B H 1.070804 0.838165 0.931429 0.110 Uiso 0.420(10) 1 calc R U P A 2
C30B C 1.1076(12) 0.7314(9) 0.9478(7) 0.078(4) Uani 0.420(10) 1 d D . P A 2
H30C H 1.211026 0.739507 0.950629 0.094 Uiso 0.420(10) 1 calc R U P A 2
H30D H 1.080284 0.685019 0.919596 0.094 Uiso 0.420(10) 1 calc R U P A 2
C31B C 1.0634(15) 0.7274(8) 1.0219(6) 0.117(5) Uani 0.420(10) 1 d D . P A 2
H31D H 1.086359 0.775278 1.047168 0.176 Uiso 0.420(10) 1 calc R U P A 2
H31E H 1.114067 0.685908 1.049093 0.176 Uiso 0.420(10) 1 calc R U P A 2
H31F H 0.961069 0.718321 1.017210 0.176 Uiso 0.420(10) 1 calc R U P A 2
H21 H 0.437(2) 0.8715(14) 0.8549(12) 0.035(6) Uiso 1 1 d . . . . .
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'
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'
Br Br -0.2901 2.4595 '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
C7 O1 C8 117.61(18) . .
C27 O2 H2 109.5 . .
C10 N1 C28 122.6(3) . .
C10 N1 H1 118.7 . .
C28 N1 H1 118.7 . .
N4 N3 C20 118.25(19) . .
N4 N3 C1 127.18(18) . .
C20 N3 C1 114.55(19) . .
C21 N4 N3 121.6(2) . .
N3 C1 C2 111.55(17) . .
N3 C1 C13 111.51(17) . .
C2 C1 C13 110.31(18) . .
N3 C1 C14 99.18(17) . .
C2 C1 C14 111.39(17) . .
C13 C1 C14 112.51(18) . .
C7 C2 C3 117.2(2) . .
C7 C2 C1 120.4(2) . .
C3 C2 C1 122.3(2) . .
C4 C3 C2 123.5(2) . .
C4 C3 H3 118.2 . .
C2 C3 H3 118.2 . .
C3 C4 C5 117.7(2) . .
C3 C4 C33 121.1(3) . .
C5 C4 C33 121.2(3) . .
C6 C5 N2B 121.5(3) . .
C6 C5 N2A 121.5(3) . .
C6 C5 C4 119.8(2) . .
N2B C5 C4 118.7(3) . .
N2A C5 C4 118.7(3) . .
C5 C6 C7 120.1(3) . .
C5 C6 H6 119.9 . .
C7 C6 H6 119.9 . .
O1 C7 C2 123.1(2) . .
O1 C7 C6 115.3(2) . .
C2 C7 C6 121.6(2) . .
C13 C8 O1 122.8(2) . .
C13 C8 C9 122.1(2) . .
O1 C8 C9 115.1(2) . .
C10 C9 C8 120.1(3) . .
C10 C9 H9 120.0 . .
C8 C9 H9 120.0 . .
C9 C10 N1 120.8(3) . .
C9 C10 C11 119.4(2) . .
N1 C10 C11 119.8(3) . .
C12 C11 C10 118.0(3) . .
C12 C11 C32 120.8(3) . .
C10 C11 C32 121.2(3) . .
C11 C12 C13 123.6(3) . .
C11 C12 H12 118.2 . .
C13 C12 H12 118.2 . .
C8 C13 C12 116.7(2) . .
C8 C13 C1 120.6(2) . .
C12 C13 C1 122.6(2) . .
C19 C14 C15 121.0(2) . .
C19 C14 C1 110.9(2) . .
C15 C14 C1 128.1(2) . .
C14 C15 C16 117.4(3) . .
C14 C15 H15 121.3 . .
C16 C15 H15 121.3 . .
C17 C16 C15 121.9(3) . .
C17 C16 H16 119.1 . .
C15 C16 H16 119.1 . .
C18 C17 C16 120.4(3) . .
C18 C17 H17 119.8 . .
C16 C17 H17 119.8 . .
C17 C18 C19 118.5(3) . .
C17 C18 H18 120.7 . .
C19 C18 H18 120.7 . .
C14 C19 C18 120.8(3) . .
C14 C19 C20 110.0(2) . .
C18 C19 C20 129.2(3) . .
O3 C20 N3 124.9(2) . .
O3 C20 C19 129.7(2) . .
N3 C20 C19 105.4(2) . .
N4 C21 C22 120.1(2) . .
N4 C21 H21 126.0(15) . .
C22 C21 H21 113.9(15) . .
C23 C22 C27 118.9(2) . .
C23 C22 C21 119.1(2) . .
C27 C22 C21 121.9(2) . .
C24 C23 C22 121.0(2) . .
C24 C23 H23 119.5 . .
C22 C23 H23 119.5 . .
C25 C24 C23 120.0(2) . .
C25 C24 Br1 119.77(19) . .
C23 C24 Br1 120.22(19) . .
C24 C25 C26 119.7(2) . .
C24 C25 H25 120.1 . .
C26 C25 H25 120.1 . .
C25 C26 C27 121.2(2) . .
C25 C26 H26 119.4 . .
C27 C26 H26 119.4 . .
O2 C27 C26 117.8(2) . .
O2 C27 C22 123.1(2) . .
C26 C27 C22 119.1(2) . .
N1 C28 C29 110.8(4) . .
N1 C28 H28A 109.5 . .
C29 C28 H28A 109.5 . .
N1 C28 H28B 109.5 . .
C29 C28 H28B 109.5 . .
H28A C28 H28B 108.1 . .
C28 C29 H29A 109.5 . .
C28 C29 H29B 109.5 . .
H29A C29 H29B 109.5 . .
C28 C29 H29C 109.5 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
C11 C32 H32A 109.5 . .
C11 C32 H32B 109.5 . .
H32A C32 H32B 109.5 . .
C11 C32 H32C 109.5 . .
H32A C32 H32C 109.5 . .
H32B C32 H32C 109.5 . .
C4 C33 H33A 109.5 . .
C4 C33 H33B 109.5 . .
H33A C33 H33B 109.5 . .
C4 C33 H33C 109.5 . .
H33A C33 H33C 109.5 . .
H33B C33 H33C 109.5 . .
C5 N2A C30A 115.9(4) . .
C5 N2A H2A 122.0 . .
C30A N2A H2A 122.0 . .
C31A C30A N2A 107.3(8) . .
C31A C30A H30A 110.3 . .
N2A C30A H30A 110.3 . .
C31A C30A H30B 110.3 . .
N2A C30A H30B 110.3 . .
H30A C30A H30B 108.5 . .
C30A C31A H31A 109.5 . .
C30A C31A H31B 109.5 . .
H31A C31A H31B 109.5 . .
C30A C31A H31C 109.5 . .
H31A C31A H31C 109.5 . .
H31B C31A H31C 109.5 . .
C30B N2B C5 132.3(6) . .
C30B N2B H2B 113.9 . .
C5 N2B H2B 113.9 . .
N2B C30B C31B 101.5(10) . .
N2B C30B H30C 111.5 . .
C31B C30B H30C 111.5 . .
N2B C30B H30D 111.5 . .
C31B C30B H30D 111.5 . .
H30C C30B H30D 109.3 . .
C30B C31B H31D 109.5 . .
C30B C31B H31E 109.5 . .
H31D C31B H31E 109.5 . .
C30B C31B H31F 109.5 . .
H31D C31B H31F 109.5 . .
H31E C31B H31F 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C24 1.894(2) .
O1 C7 1.370(3) .
O1 C8 1.385(3) .
O2 C27 1.353(3) .
O2 H2 0.8200 .
O3 C20 1.214(3) .
N1 C10 1.385(3) .
N1 C28 1.440(5) .
N1 H1 0.8600 .
N3 N4 1.359(3) .
N3 C20 1.382(3) .
N3 C1 1.492(3) .
N4 C21 1.273(3) .
C1 C2 1.517(3) .
C1 C13 1.518(3) .
C1 C14 1.524(3) .
C2 C7 1.378(3) .
C2 C3 1.390(3) .
C3 C4 1.374(3) .
C3 H3 0.9300 .
C4 C5 1.411(4) .
C4 C33 1.497(4) .
C5 C6 1.383(4) .
C5 N2B 1.385(3) .
C5 N2A 1.385(3) .
C6 C7 1.383(3) .
C6 H6 0.9300 .
C8 C13 1.373(3) .
C8 C9 1.391(3) .
C9 C10 1.380(4) .
C9 H9 0.9300 .
C10 C11 1.411(4) .
C11 C12 1.378(3) .
C11 C32 1.508(4) .
C12 C13 1.389(3) .
C12 H12 0.9300 .
C14 C19 1.376(3) .
C14 C15 1.377(3) .
C15 C16 1.390(4) .
C15 H15 0.9300 .
C16 C17 1.370(4) .
C16 H16 0.9300 .
C17 C18 1.369(4) .
C17 H17 0.9300 .
C18 C19 1.389(4) .
C18 H18 0.9300 .
C19 C20 1.459(4) .
C21 C22 1.456(3) .
C21 H21 0.87(2) .
C22 C23 1.386(3) .
C22 C27 1.405(3) .
C23 C24 1.377(3) .
C23 H23 0.9300 .
C24 C25 1.375(4) .
C25 C26 1.377(4) .
C25 H25 0.9300 .
C26 C27 1.380(3) .
C26 H26 0.9300 .
C28 C29 1.529(5) .
C28 H28A 0.9700 .
C28 H28B 0.9700 .
C29 H29A 0.9600 .
C29 H29B 0.9600 .
C29 H29C 0.9600 .
C32 H32A 0.9600 .
C32 H32B 0.9600 .
C32 H32C 0.9600 .
C33 H33A 0.9600 .
C33 H33B 0.9600 .
C33 H33C 0.9600 .
N2A C30A 1.563(12) .
N2A H2A 0.8600 .
C30A C31A 1.493(11) .
C30A H30A 0.9700 .
C30A H30B 0.9700 .
C31A H31A 0.9600 .
C31A H31B 0.9600 .
C31A H31C 0.9600 .
N2B C30B 1.376(14) .
N2B H2B 0.8600 .
C30B C31B 1.487(14) .
C30B H30C 0.9700 .
C30B H30D 0.9700 .
C31B H31D 0.9600 .
C31B H31E 0.9600 .
C31B H31F 0.9600 .
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
_geom_hbond_publ_flag
O2 H2 N4 0.82 1.91 2.621(2) 144.2 . yes
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
C20 N3 N4 C21 -177.9(2) . . . .
C1 N3 N4 C21 3.6(3) . . . .
N4 N3 C1 C2 -63.3(3) . . . .
C20 N3 C1 C2 118.1(2) . . . .
N4 N3 C1 C13 60.5(3) . . . .
C20 N3 C1 C13 -118.0(2) . . . .
N4 N3 C1 C14 179.24(19) . . . .
C20 N3 C1 C14 0.7(2) . . . .
N3 C1 C2 C7 143.7(2) . . . .
C13 C1 C2 C7 19.2(3) . . . .
C14 C1 C2 C7 -106.5(2) . . . .
N3 C1 C2 C3 -38.9(3) . . . .
C13 C1 C2 C3 -163.36(19) . . . .
C14 C1 C2 C3 71.0(3) . . . .
C7 C2 C3 C4 0.5(3) . . . .
C1 C2 C3 C4 -177.0(2) . . . .
C2 C3 C4 C5 -0.5(4) . . . .
C2 C3 C4 C33 179.3(2) . . . .
C3 C4 C5 C6 0.0(4) . . . .
C33 C4 C5 C6 -179.9(2) . . . .
C3 C4 C5 N2B -179.6(2) . . . .
C33 C4 C5 N2B 0.6(4) . . . .
C3 C4 C5 N2A -179.6(2) . . . .
C33 C4 C5 N2A 0.6(4) . . . .
N2B C5 C6 C7 -179.9(2) . . . .
N2A C5 C6 C7 -179.9(2) . . . .
C4 C5 C6 C7 0.6(4) . . . .
C8 O1 C7 C2 -16.3(3) . . . .
C8 O1 C7 C6 163.4(2) . . . .
C3 C2 C7 O1 179.8(2) . . . .
C1 C2 C7 O1 -2.6(3) . . . .
C3 C2 C7 C6 0.0(3) . . . .
C1 C2 C7 C6 177.7(2) . . . .
C5 C6 C7 O1 179.7(2) . . . .
C5 C6 C7 C2 -0.6(4) . . . .
C7 O1 C8 C13 16.8(3) . . . .
C7 O1 C8 C9 -163.2(2) . . . .
C13 C8 C9 C10 -0.6(4) . . . .
O1 C8 C9 C10 179.4(2) . . . .
C8 C9 C10 N1 -178.2(2) . . . .
C8 C9 C10 C11 1.7(4) . . . .
C28 N1 C10 C9 6.5(4) . . . .
C28 N1 C10 C11 -173.3(3) . . . .
C9 C10 C11 C12 -1.8(4) . . . .
N1 C10 C11 C12 178.1(2) . . . .
C9 C10 C11 C32 177.3(2) . . . .
N1 C10 C11 C32 -2.8(4) . . . .
C10 C11 C12 C13 0.8(4) . . . .
C32 C11 C12 C13 -178.3(2) . . . .
O1 C8 C13 C12 179.6(2) . . . .
C9 C8 C13 C12 -0.5(3) . . . .
O1 C8 C13 C1 1.8(3) . . . .
C9 C8 C13 C1 -178.3(2) . . . .
C11 C12 C13 C8 0.4(3) . . . .
C11 C12 C13 C1 178.1(2) . . . .
N3 C1 C13 C8 -143.3(2) . . . .
C2 C1 C13 C8 -18.7(3) . . . .
C14 C1 C13 C8 106.3(2) . . . .
N3 C1 C13 C12 39.1(3) . . . .
C2 C1 C13 C12 163.62(19) . . . .
C14 C1 C13 C12 -71.3(3) . . . .
N3 C1 C14 C19 0.0(2) . . . .
C2 C1 C14 C19 -117.6(2) . . . .
C13 C1 C14 C19 118.0(2) . . . .
N3 C1 C14 C15 179.0(2) . . . .
C2 C1 C14 C15 61.4(3) . . . .
C13 C1 C14 C15 -63.0(3) . . . .
C19 C14 C15 C16 0.4(4) . . . .
C1 C14 C15 C16 -178.5(2) . . . .
C14 C15 C16 C17 -0.4(4) . . . .
C15 C16 C17 C18 0.5(5) . . . .
C16 C17 C18 C19 -0.6(6) . . . .
C15 C14 C19 C18 -0.5(4) . . . .
C1 C14 C19 C18 178.6(3) . . . .
C15 C14 C19 C20 -179.7(2) . . . .
C1 C14 C19 C20 -0.7(3) . . . .
C17 C18 C19 C14 0.6(5) . . . .
C17 C18 C19 C20 179.7(3) . . . .
N4 N3 C20 O3 1.4(4) . . . .
C1 N3 C20 O3 -179.9(3) . . . .
N4 N3 C20 C19 -179.78(19) . . . .
C1 N3 C20 C19 -1.1(3) . . . .
C14 C19 C20 O3 179.8(3) . . . .
C18 C19 C20 O3 0.7(5) . . . .
C14 C19 C20 N3 1.0(3) . . . .
C18 C19 C20 N3 -178.1(3) . . . .
N3 N4 C21 C22 -179.00(19) . . . .
N4 C21 C22 C23 177.8(2) . . . .
N4 C21 C22 C27 0.6(3) . . . .
C27 C22 C23 C24 0.0(3) . . . .
C21 C22 C23 C24 -177.3(2) . . . .
C22 C23 C24 C25 -0.5(4) . . . .
C22 C23 C24 Br1 179.85(17) . . . .
C23 C24 C25 C26 0.5(4) . . . .
Br1 C24 C25 C26 -179.8(2) . . . .
C24 C25 C26 C27 0.0(4) . . . .
C25 C26 C27 O2 179.0(2) . . . .
C25 C26 C27 C22 -0.4(4) . . . .
C23 C22 C27 O2 -178.9(2) . . . .
C21 C22 C27 O2 -1.7(4) . . . .
C23 C22 C27 C26 0.4(3) . . . .
C21 C22 C27 C26 177.7(2) . . . .
C10 N1 C28 C29 172.7(3) . . . .
C6 C5 N2A C30A -4.3(6) . . . .
C4 C5 N2A C30A 175.2(5) . . . .
C5 N2A C30A C31A 175.3(6) . . . .
C6 C5 N2B C30B 23.4(8) . . . .
C4 C5 N2B C30B -157.1(7) . . . .
C5 N2B C30B C31B -98.2(9) . . . .
