#------------------------------------------------------------------------------
#$Date: 2024-05-04 04:52:17 +0300 (Sat, 04 May 2024) $
#$Revision: 291490 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/31/2023116.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2023116
loop_
_publ_author_name
'Gorbunov, Alexander'
'Bezzubov, Stanislav'
'Malakhova, Maria'
'Kovalev, Vladimir'
'Vatsouro, Ivan'
_publ_section_title
;
 Synthesis and crystal structures of
 5,17-dibromo-26,28-dihydroxy-25,27-dipropynyloxycalix[4]arene,
 5,17-dibromo-26,28-dipropoxy-25,27-dipropynyloxycalix[4]arene and
 25,27-bis(2-azidoethoxy)-5,17-dibromo-26,28-dihydroxycalix[4]arene
;
_journal_issue                   6
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989024003785
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C32 H28 Br2 N6 O4'
_chemical_formula_moiety         'C32 H28 Br2 N6 O4'
_chemical_formula_sum            'C32 H28 Br2 N6 O4'
_chemical_formula_weight         720.42
_chemical_name_systematic
;
25,27-Bis(2-azidoethoxy)-5,17-dibromo-26,28-dihydroxycalix[4]arene
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   36.3261(7)
_cell_length_b                   36.3261(7)
_cell_length_c                   12.1054(4)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.311
_cell_measurement_theta_min      2.243
_cell_volume                     13834.0(6)
_computing_cell_refinement
;
APEX3 (Bruker, 2017)
;
_computing_data_collection
;
APEX3 (Bruker, 2017)
;
_computing_data_reduction
;
SAINT (Bruker, 2017)
;
_computing_molecular_graphics
;
Olex2 1.3 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
Olex2 1.3 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTON III CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            45251
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.499
_diffrn_reflns_theta_min         1.802
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.685
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_description       block
_exptl_crystal_F_000             6552
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.298
_refine_diff_density_min         -1.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         7804
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0383P)²+55.0341P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0974
_reflns_number_gt                6043
_reflns_number_total             7804
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm5716.cif
_cod_data_source_block           3
_cod_original_cell_volume        13834.0(7)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               2023116
_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   0.437
_shelx_estimated_absorpt_t_max   0.775
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br2 0.77808(2) 0.64422(2) 0.11845(2) 0.02592(8) Uani d 1 . .
Br Br1 0.94747(2) 0.64087(2) 1.04746(3) 0.03614(9) Uani d 1 . .
O O4 0.73344(6) 0.53322(6) 0.69360(15) 0.0235(4) Uani d 1 . .
O O3 0.76702(7) 0.53195(7) 0.49646(16) 0.0304(5) Uani d 1 . .
H H3 0.754079 0.534255 0.551158 0.046 Uiso calc 1 . .
O O1 0.81215(6) 0.53626(7) 0.71561(16) 0.0296(4) Uani d 1 . .
H H1 0.821251 0.526224 0.667258 0.044 Uiso calc 1 . .
O O2 0.82909(7) 0.50491(6) 0.52611(17) 0.0317(5) Uani d 1 . .
C C16 0.75008(8) 0.60698(9) 0.3311(2) 0.0237(5) Uani d 1 . .
H H16 0.735357 0.622450 0.332302 0.028 Uiso calc 1 . .
C C15 0.77434(8) 0.60962(9) 0.2407(2) 0.0233(5) Uani d 1 . .
C C3 0.90557(9) 0.61047(9) 0.9377(2) 0.0260(6) Uani d 1 . .
C C2 0.86500(9) 0.60483(9) 0.9485(2) 0.0241(5) Uani d 1 . .
H H2 0.858609 0.617607 1.008329 0.029 Uiso calc 1 . .
C C24 0.78870(8) 0.57243(9) 0.8817(2) 0.0231(5) Uani d 1 . .
H H24A 0.784545 0.580534 0.956822 0.028 Uiso calc 1 . .
H H24B 0.768569 0.541658 0.872265 0.028 Uiso calc 1 . .
C C10 0.89056(9) 0.60072(9) 0.3603(2) 0.0274(6) Uani d 1 . .
H H10 0.889258 0.612151 0.290757 0.033 Uiso calc 1 . .
C C20 0.76455(9) 0.64427(10) 0.6366(2) 0.0296(6) Uani d 1 . .
H H20 0.760226 0.660610 0.582331 0.036 Uiso calc 1 . .
C C17 0.74717(8) 0.58147(9) 0.4209(2) 0.0241(5) Uani d 1 . .
C C11 0.85771(9) 0.56095(9) 0.3911(2) 0.0255(6) Uani d 1 . .
C C14 0.79580(8) 0.58721(9) 0.2352(2) 0.0238(5) Uani d 1 . .
H H14 0.812203 0.589504 0.171789 0.029 Uiso calc 1 . .
C C19 0.74568(9) 0.60024(9) 0.6231(2) 0.0257(6) Uani d 1 . .
C C25 0.84464(9) 0.56262(9) 0.7832(2) 0.0248(6) Uani d 1 . .
C C28 0.75217(8) 0.57733(9) 0.7062(2) 0.0226(5) Uani d 1 . .
C C13 0.79333(8) 0.56136(9) 0.3226(2) 0.0241(5) Uani d 1 . .
C C8 0.92731(9) 0.60764(10) 0.5302(2) 0.0308(6) Uani d 1 . .
H H8 0.950790 0.624029 0.577501 0.037 Uiso calc 1 . .
C C1 0.83381(9) 0.58053(9) 0.8717(2) 0.0231(5) Uani d 1 . .
C C5 0.88617(9) 0.56989(9) 0.7704(2) 0.0277(6) Uani d 1 . .
C C23 0.77852(8) 0.59706(9) 0.7970(2) 0.0227(5) Uani d 1 . .
C C22 0.79695(9) 0.64103(9) 0.8067(2) 0.0274(6) Uani d 1 . .
H H22 0.814878 0.655309 0.867784 0.033 Uiso calc 1 . .
C C21 0.78926(10) 0.66417(10) 0.7275(2) 0.0304(6) Uani d 1 . .
H H21 0.801203 0.693985 0.736316 0.037 Uiso calc 1 . .
C C7 0.89577(9) 0.56776(10) 0.5635(2) 0.0277(6) Uani d 1 . .
C C4 0.91627(9) 0.59369(10) 0.8493(2) 0.0296(6) Uani d 1 . .
H H4 0.944407 0.598510 0.842644 0.036 Uiso calc 1 . .
C C26 0.86166(9) 0.54477(9) 0.4921(2) 0.0261(6) Uani d 1 . .
C C27 0.76893(9) 0.55853(9) 0.4151(2) 0.0248(6) Uani d 1 . .
C C18 0.72006(9) 0.57839(10) 0.5199(2) 0.0287(6) Uani d 1 . .
H H18A 0.700519 0.548016 0.536836 0.034 Uiso calc 1 . .
H H18B 0.702496 0.591249 0.500219 0.034 Uiso calc 1 . .
C C31 0.69060(9) 0.50925(10) 0.7339(2) 0.0309(6) Uani d 1 . .
H H31A 0.674011 0.522648 0.709611 0.037 Uiso calc 1 . .
H H31B 0.690578 0.508623 0.815710 0.037 Uiso calc 1 . .
C C9 0.92504(9) 0.62399(10) 0.4281(3) 0.0316(6) Uani d 1 . .
H H9 0.947183 0.651128 0.405307 0.038 Uiso calc 1 . .
N N4 0.66469(11) 0.46548(11) 0.5687(3) 0.0530(8) Uani d 1 . .
C C6 0.89773(11) 0.55028(11) 0.6759(2) 0.0337(7) Uani d 1 . .
H H6A 0.878111 0.519168 0.676259 0.040 Uiso calc 1 . .
H H6B 0.926863 0.555358 0.687975 0.040 Uiso calc 1 . .
C C12 0.81799(9) 0.53781(10) 0.3211(2) 0.0293(6) Uani d 1 . .
H H12A 0.799872 0.508657 0.350041 0.035 Uiso calc 1 . .
H H12B 0.825950 0.535615 0.244215 0.035 Uiso calc 1 . .
C C32 0.67100(10) 0.46485(11) 0.6891(3) 0.0393(7) Uani d 1 . .
H H32A 0.689825 0.453040 0.704496 0.047 Uiso calc 1 . .
H H32B 0.643333 0.446505 0.725666 0.047 Uiso calc 1 . .
C C29 0.83526(12) 0.47048(10) 0.4902(3) 0.0410(8) Uani d 1 . .
H H29A 0.860714 0.472574 0.526160 0.049 Uiso calc 1 . .
H H29B 0.839456 0.471768 0.409152 0.049 Uiso calc 1 . .
N N5 0.68006(13) 0.44967(14) 0.5103(3) 0.0736(11) Uani d 1 . .
C C30 0.79672(14) 0.42988(11) 0.5213(4) 0.0551(10) Uani d 1 . .
H H30A 0.797717 0.405718 0.486638 0.066 Uiso calc 1 . .
H H30B 0.770974 0.429853 0.494378 0.066 Uiso calc 1 . .
N N6 0.69206(17) 0.43548(18) 0.4454(4) 0.1068(16) Uani d 1 . .
N N1 0.79469(12) 0.42496(12) 0.6448(3) 0.0627(10) Uani d 1 . .
N N2 0.76567(14) 0.42481(14) 0.6888(3) 0.0696(10) Uani d 1 . .
N N3 0.74014(17) 0.42453(19) 0.7425(4) 0.0991(13) Uani d 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C28 O4 C31 . . 114.6(2) ?
C27 O3 H3 . . 109.5 ?
C25 O1 H1 . . 109.5 ?
C26 O2 C29 . . 113.0(2) ?
C15 C16 H16 . . 120.1 ?
C15 C16 C17 . . 119.8(2) ?
C17 C16 H16 . . 120.1 ?
C16 C15 Br2 . . 119.7(2) ?
C16 C15 C14 . . 121.8(2) ?
C14 C15 Br2 . . 118.5(2) ?
C2 C3 Br1 . . 120.1(2) ?
C4 C3 Br1 . . 118.5(2) ?
C4 C3 C2 . . 121.3(3) ?
C3 C2 H2 . . 120.0 ?
C1 C2 C3 . . 120.0(3) ?
C1 C2 H2 . . 120.0 ?
H24A C24 H24B . . 107.8 ?
C1 C24 H24A . . 109.0 ?
C1 C24 H24B . . 109.0 ?
C1 C24 C23 . . 112.8(2) ?
C23 C24 H24A . . 109.0 ?
C23 C24 H24B . . 109.0 ?
C11 C10 H10 . . 119.2 ?
C9 C10 H10 . . 119.2 ?
C9 C10 C11 . . 121.5(3) ?
C19 C20 H20 . . 119.6 ?
C21 C20 H20 . . 119.6 ?
C21 C20 C19 . . 120.8(3) ?
C16 C17 C27 . . 118.3(2) ?
C16 C17 C18 . . 119.6(2) ?
C27 C17 C18 . . 122.1(2) ?
C10 C11 C26 . . 117.3(3) ?
C10 C11 C12 . . 120.8(3) ?
C26 C11 C12 . . 121.8(3) ?
C15 C14 H14 . . 120.1 ?
C15 C14 C13 . . 119.9(2) ?
C13 C14 H14 . . 120.1 ?
C20 C19 C18 . . 120.9(2) ?
C28 C19 C20 . . 117.6(3) ?
C28 C19 C18 . . 121.4(3) ?
O1 C25 C1 . . 116.0(2) ?
O1 C25 C5 . . 122.6(2) ?
C5 C25 C1 . . 121.3(3) ?
C19 C28 O4 . . 118.2(2) ?
C23 C28 O4 . . 119.3(2) ?
C23 C28 C19 . . 122.4(3) ?
C14 C13 C27 . . 118.9(2) ?
C14 C13 C12 . . 121.1(2) ?
C27 C13 C12 . . 119.9(2) ?
C7 C8 H8 . . 119.6 ?
C7 C8 C9 . . 120.7(3) ?
C9 C8 H8 . . 119.6 ?
C2 C1 C24 . . 121.9(2) ?
C2 C1 C25 . . 118.4(2) ?
C25 C1 C24 . . 119.7(2) ?
C25 C5 C6 . . 121.3(3) ?
C4 C5 C25 . . 118.8(3) ?
C4 C5 C6 . . 119.8(3) ?
C28 C23 C24 . . 122.3(2) ?
C22 C23 C24 . . 119.8(3) ?
C22 C23 C28 . . 117.9(2) ?
C23 C22 H22 . . 119.8 ?
C21 C22 C23 . . 120.5(3) ?
C21 C22 H22 . . 119.8 ?
C20 C21 C22 . . 120.6(3) ?
C20 C21 H21 . . 119.7 ?
C22 C21 H21 . . 119.7 ?
C8 C7 C26 . . 118.0(3) ?
C8 C7 C6 . . 120.8(3) ?
C26 C7 C6 . . 121.2(3) ?
C3 C4 C5 . . 120.2(3) ?
C3 C4 H4 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
C11 C26 O2 . . 118.9(3) ?
C7 C26 O2 . . 118.5(3) ?
C7 C26 C11 . . 122.6(3) ?
O3 C27 C17 . . 122.8(2) ?
O3 C27 C13 . . 116.0(2) ?
C13 C27 C17 . . 121.2(2) ?
C17 C18 C19 . . 113.8(2) ?
C17 C18 H18A . . 108.8 ?
C17 C18 H18B . . 108.8 ?
C19 C18 H18A . . 108.8 ?
C19 C18 H18B . . 108.8 ?
H18A C18 H18B . . 107.7 ?
O4 C31 H31A . . 110.0 ?
O4 C31 H31B . . 110.0 ?
O4 C31 C32 . . 108.4(2) ?
H31A C31 H31B . . 108.4 ?
C32 C31 H31A . . 110.0 ?
C32 C31 H31B . . 110.0 ?
C10 C9 C8 . . 119.8(3) ?
C10 C9 H9 . . 120.1 ?
C8 C9 H9 . . 120.1 ?
N5 N4 C32 . . 117.2(4) ?
C5 C6 C7 . . 113.5(2) ?
C5 C6 H6A . . 108.9 ?
C5 C6 H6B . . 108.9 ?
C7 C6 H6A . . 108.9 ?
C7 C6 H6B . . 108.9 ?
H6A C6 H6B . . 107.7 ?
C11 C12 C13 . . 110.4(2) ?
C11 C12 H12A . . 109.6 ?
C11 C12 H12B . . 109.6 ?
C13 C12 H12A . . 109.6 ?
C13 C12 H12B . . 109.6 ?
H12A C12 H12B . . 108.1 ?
C31 C32 H32A . . 109.8 ?
C31 C32 H32B . . 109.8 ?
N4 C32 C31 . . 109.5(3) ?
N4 C32 H32A . . 109.8 ?
N4 C32 H32B . . 109.8 ?
H32A C32 H32B . . 108.2 ?
O2 C29 H29A . . 110.1 ?
O2 C29 H29B . . 110.1 ?
O2 C29 C30 . . 107.8(3) ?
H29A C29 H29B . . 108.5 ?
C30 C29 H29A . . 110.1 ?
C30 C29 H29B . . 110.1 ?
N6 N5 N4 . . 172.0(6) ?
C29 C30 H30A . . 109.7 ?
C29 C30 H30B . . 109.7 ?
C29 C30 N1 . . 109.6(3) ?
H30A C30 H30B . . 108.2 ?
N1 C30 H30A . . 109.7 ?
N1 C30 H30B . . 109.7 ?
N2 N1 C30 . . 116.2(4) ?
N3 N2 N1 . . 171.8(5) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br2 C15 . 1.902(3) ?
Br1 C3 . 1.903(3) ?
O4 C28 . 1.401(3) ?
O4 C31 . 1.436(3) ?
O3 H3 . 0.8400 ?
O3 C27 . 1.356(3) ?
O1 H1 . 0.8400 ?
O1 C25 . 1.360(3) ?
O2 C26 . 1.397(3) ?
O2 C29 . 1.444(3) ?
C16 H16 . 0.9500 ?
C16 C15 . 1.377(4) ?
C16 C17 . 1.399(4) ?
C15 C14 . 1.382(4) ?
C3 C2 . 1.389(4) ?
C3 C4 . 1.380(4) ?
C2 H2 . 0.9500 ?
C2 C1 . 1.388(4) ?
C24 H24A . 0.9900 ?
C24 H24B . 0.9900 ?
C24 C1 . 1.518(4) ?
C24 C23 . 1.523(4) ?
C10 H10 . 0.9500 ?
C10 C11 . 1.388(4) ?
C10 C9 . 1.378(4) ?
C20 H20 . 0.9500 ?
C20 C19 . 1.400(4) ?
C20 C21 . 1.374(4) ?
C17 C27 . 1.408(4) ?
C17 C18 . 1.519(4) ?
C11 C26 . 1.394(4) ?
C11 C12 . 1.515(4) ?
C14 H14 . 0.9500 ?
C14 C13 . 1.387(4) ?
C19 C28 . 1.399(4) ?
C19 C18 . 1.522(4) ?
C25 C1 . 1.408(4) ?
C25 C5 . 1.404(4) ?
C28 C23 . 1.397(4) ?
C13 C27 . 1.400(4) ?
C13 C12 . 1.517(4) ?
C8 H8 . 0.9500 ?
C8 C7 . 1.383(4) ?
C8 C9 . 1.391(4) ?
C5 C4 . 1.382(4) ?
C5 C6 . 1.514(4) ?
C23 C22 . 1.394(4) ?
C22 H22 . 0.9500 ?
C22 C21 . 1.392(4) ?
C21 H21 . 0.9500 ?
C7 C26 . 1.394(4) ?
C7 C6 . 1.519(4) ?
C4 H4 . 0.9500 ?
C18 H18A . 0.9900 ?
C18 H18B . 0.9900 ?
C31 H31A . 0.9900 ?
C31 H31B . 0.9900 ?
C31 C32 . 1.501(5) ?
C9 H9 . 0.9500 ?
N4 C32 . 1.477(4) ?
N4 N5 . 1.209(5) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C32 H32A . 0.9900 ?
C32 H32B . 0.9900 ?
C29 H29A . 0.9900 ?
C29 H29B . 0.9900 ?
C29 C30 . 1.488(5) ?
N5 N6 . 1.139(6) ?
C30 H30A . 0.9900 ?
C30 H30B . 0.9900 ?
C30 N1 . 1.502(5) ?
N1 N2 . 1.179(5) ?
N2 N3 . 1.128(6) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H3 O4 . 0.84 1.87 2.691(3) 164.1 yes
O1 H1 O2 . 0.84 1.95 2.764(3) 161.5 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Br2 C15 C14 C13 . . . . -179.3(2) ?
Br1 C3 C2 C1 . . . . -176.2(2) ?
Br1 C3 C4 C5 . . . . 177.3(2) ?
O4 C28 C23 C24 . . . . 1.7(4) ?
O4 C28 C23 C22 . . . . 179.5(2) ?
O4 C31 C32 N4 . . . . -69.0(3) ?
O1 C25 C1 C2 . . . . 174.8(2) ?
O1 C25 C1 C24 . . . . -4.4(4) ?
O1 C25 C5 C4 . . . . -173.5(3) ?
O1 C25 C5 C6 . . . . 3.1(4) ?
O2 C29 C30 N1 . . . . -69.2(4) ?
C16 C15 C14 C13 . . . . -0.3(4) ?
C16 C17 C27 O3 . . . . -177.9(3) ?
C16 C17 C27 C13 . . . . 0.7(4) ?
C16 C17 C18 C19 . . . . -109.8(3) ?
C15 C16 C17 C27 . . . . -1.0(4) ?
C15 C16 C17 C18 . . . . -179.5(3) ?
C15 C14 C13 C27 . . . . 0.0(4) ?
C15 C14 C13 C12 . . . . -177.4(2) ?
C3 C2 C1 C24 . . . . 178.3(2) ?
C3 C2 C1 C25 . . . . -0.9(4) ?
C2 C3 C4 C5 . . . . -1.5(4) ?
C24 C23 C22 C21 . . . . 177.5(2) ?
C10 C11 C26 O2 . . . . 179.7(2) ?
C10 C11 C26 C7 . . . . 3.3(4) ?
C10 C11 C12 C13 . . . . -66.7(3) ?
C20 C19 C28 O4 . . . . -180.0(2) ?
C20 C19 C28 C23 . . . . -4.0(4) ?
C20 C19 C18 C17 . . . . 80.6(3) ?
C17 C16 C15 Br2 . . . . 179.8(2) ?
C17 C16 C15 C14 . . . . 0.8(4) ?
C11 C10 C9 C8 . . . . -0.1(4) ?
C14 C13 C27 O3 . . . . 178.5(2) ?
C14 C13 C27 C17 . . . . -0.2(4) ?
C14 C13 C12 C11 . . . . 100.8(3) ?
C19 C20 C21 C22 . . . . 1.7(4) ?
C19 C28 C23 C24 . . . . -174.3(2) ?
C19 C28 C23 C22 . . . . 3.5(4) ?
C25 C5 C4 C3 . . . . -1.1(4) ?
C25 C5 C6 C7 . . . . 67.5(4) ?
C28 O4 C31 C32 . . . . 165.3(2) ?
C28 C19 C18 C17 . . . . -97.7(3) ?
C28 C23 C22 C21 . . . . -0.4(4) ?
C8 C7 C26 O2 . . . . -178.4(2) ?
C8 C7 C26 C11 . . . . -2.0(4) ?
C8 C7 C6 C5 . . . . 75.5(4) ?
C1 C24 C23 C28 . . . . 106.9(3) ?
C1 C24 C23 C22 . . . . -70.9(3) ?
C1 C25 C5 C4 . . . . 2.7(4) ?
C1 C25 C5 C6 . . . . 179.4(3) ?
C5 C25 C1 C2 . . . . -1.7(4) ?
C5 C25 C1 C24 . . . . 179.1(2) ?
C23 C24 C1 C2 . . . . 107.3(3) ?
C23 C24 C1 C25 . . . . -73.5(3) ?
C23 C22 C21 C20 . . . . -2.2(4) ?
C21 C20 C19 C28 . . . . 1.3(4) ?
C21 C20 C19 C18 . . . . -177.0(2) ?
C7 C8 C9 C10 . . . . 1.5(4) ?
C4 C3 C2 C1 . . . . 2.5(4) ?
C4 C5 C6 C7 . . . . -115.9(3) ?
C26 O2 C29 C30 . . . . -174.4(3) ?
C26 C11 C12 C13 . . . . 108.9(3) ?
C26 C7 C6 C5 . . . . -102.6(3) ?
C27 C17 C18 C19 . . . . 71.7(4) ?
C27 C13 C12 C11 . . . . -76.6(3) ?
C18 C17 C27 O3 . . . . 0.6(4) ?
C18 C17 C27 C13 . . . . 179.2(3) ?
C18 C19 C28 O4 . . . . -1.6(4) ?
C18 C19 C28 C23 . . . . 174.4(2) ?
C31 O4 C28 C19 . . . . -86.8(3) ?
C31 O4 C28 C23 . . . . 97.1(3) ?
C9 C10 C11 C26 . . . . -2.2(4) ?
C9 C10 C11 C12 . . . . 173.6(2) ?
C9 C8 C7 C26 . . . . -0.5(4) ?
C9 C8 C7 C6 . . . . -178.6(2) ?
C6 C5 C4 C3 . . . . -177.8(3) ?
C6 C7 C26 O2 . . . . -0.2(4) ?
C6 C7 C26 C11 . . . . 176.2(2) ?
C12 C11 C26 O2 . . . . 3.9(4) ?
C12 C11 C26 C7 . . . . -172.5(2) ?
C12 C13 C27 O3 . . . . -4.0(4) ?
C12 C13 C27 C17 . . . . 177.2(3) ?
C29 O2 C26 C11 . . . . 90.4(3) ?
C29 O2 C26 C7 . . . . -93.0(3) ?
C29 C30 N1 N2 . . . . 115.8(4) ?
N5 N4 C32 C31 . . . . 125.4(4) ?
