#------------------------------------------------------------------------------
#$Date: 2022-10-21 12:06:26 +0300 (Fri, 21 Oct 2022) $
#$Revision: 278702 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/59/8105935.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_8105935
loop_
_publ_author_name
'Su, Chang-Ming'
'Wang, Chun-Hua'
'Hou, Gui-Ge'
_publ_section_title
;
 Crystal structure of N 1,N 3-bis(2-hydroxyethyl)-N 1, N 1,N 3,N
 3-tetramethylpropane-1,3-diaminium dibromide, C11H28Br2N2O2
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1055
_journal_page_last               1057
_journal_paper_doi               10.1515/ncrs-2019-0258
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C11 H28 N2 O2, 2(Br)'
_chemical_formula_sum            'C11 H28 Br2 N2 O2'
_chemical_formula_weight         380.17
_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
_cell_angle_alpha                117.088(3)
_cell_angle_beta                 92.4590(10)
_cell_angle_gamma                108.199(2)
_cell_formula_units_Z            4
_cell_length_a                   12.0519(11)
_cell_length_b                   12.6670(12)
_cell_length_c                   12.9161(12)
_cell_measurement_reflns_used    2135
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.581
_cell_measurement_theta_min      3.132
_cell_volume                     1627.2(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0700
_diffrn_reflns_av_unetI/netI     0.1253
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8270
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.020
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_min         2.274
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    4.977
_exptl_absorpt_correction_T_max  0.4678
_exptl_absorpt_correction_T_min  0.2535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.180
_refine_diff_density_max         1.149
_refine_diff_density_min         -1.107
_refine_diff_density_rms         0.151
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.904
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         5610
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.904
_refine_ls_R_factor_all          0.1273
_refine_ls_R_factor_gt           0.0645
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0871P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1455
_refine_ls_wR_factor_ref         0.1632
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3016
_reflns_number_total             5610
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0258_suppl.cif
_cod_data_source_block           1
_cod_database_code               8105935
_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   0.254
_shelx_estimated_absorpt_t_max   0.468
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 0.48959(8) 0.06821(8) 0.27297(7) 0.0426(3) Uani 1 1 d . . . . .
Br2 Br 0.06635(8) 0.20681(9) 0.89507(8) 0.0472(3) Uani 1 1 d . . . . .
Br3 Br 0.07569(8) 0.75058(9) 0.47256(9) 0.0520(3) Uani 1 1 d . . . . .
Br4 Br 0.50123(8) 0.43624(9) 0.22863(8) 0.0573(3) Uani 1 1 d . . . . .
N1 N 0.2501(5) 0.6074(6) -0.0131(5) 0.0332(15) Uani 1 1 d . . . . .
N2 N 0.2540(5) 0.9828(5) -0.0677(5) 0.0254(14) Uani 1 1 d . . . . .
N3 N 0.2467(5) 0.5090(6) 0.4722(5) 0.0310(15) Uani 1 1 d . . . . .
N4 N 0.2520(5) 0.1357(6) 0.5234(5) 0.0315(15) Uani 1 1 d . . . . .
O1 O 0.2425(7) 0.6961(7) 0.2677(6) 0.086(2) Uani 1 1 d . . . . .
H1 H 0.212515 0.716668 0.326161 0.129 Uiso 1 1 calc R U . . .
O2 O 0.1087(5) 1.0903(5) 0.1933(5) 0.0496(15) Uani 1 1 d . . . . .
H2 H 0.065188 1.023750 0.189623 0.074 Uiso 1 1 calc R U . . .
O3 O 0.0454(5) 0.3455(6) 0.1748(5) 0.069(2) Uani 1 1 d . . . . .
H3 H 0.050742 0.310565 0.105022 0.083 Uiso 1 1 calc R U . . .
O4 O 0.4305(6) 0.1563(7) 0.7328(6) 0.072(2) Uani 1 1 d . . . . .
H4 H 0.448606 0.100862 0.737026 0.086 Uiso 1 1 calc R U . . .
C1 C 0.3175(7) 0.7283(7) -0.0128(7) 0.0316(18) Uani 1 1 d . . . . .
H1A H 0.371757 0.712182 -0.066274 0.038 Uiso 1 1 calc R U . . .
H1B H 0.365653 0.791086 0.066749 0.038 Uiso 1 1 calc R U . . .
C2 C 0.2388(7) 0.7856(7) -0.0501(7) 0.0338(19) Uani 1 1 d . . . . .
H2A H 0.192300 0.725735 -0.130811 0.041 Uiso 1 1 calc R U . . .
H2B H 0.183863 0.802772 0.002523 0.041 Uiso 1 1 calc R U . . .
C3 C 0.3202(6) 0.9094(6) -0.0428(6) 0.0278(17) Uani 1 1 d . . . . .
H3A H 0.371737 0.964290 0.036249 0.033 Uiso 1 1 calc R U . . .
H3B H 0.370931 0.889442 -0.099465 0.033 Uiso 1 1 calc R U . . .
C4 C 0.1570(8) 0.6190(8) 0.0611(7) 0.047(2) Uani 1 1 d . . . . .
H4A H 0.122831 0.539506 0.062383 0.056 Uiso 1 1 calc R U . . .
H4B H 0.093247 0.627845 0.021109 0.056 Uiso 1 1 calc R U . . .
C5 C 0.1982(9) 0.7296(10) 0.1911(8) 0.060(3) Uani 1 1 d . . . . .
H5A H 0.259842 0.803115 0.195228 0.072 Uiso 1 1 calc R U . . .
H5B H 0.131092 0.753823 0.216510 0.072 Uiso 1 1 calc R U . . .
C6 C 0.1883(8) 0.5022(8) -0.1383(7) 0.050(2) Uani 1 1 d . . . . .
H6A H 0.123027 0.517789 -0.165879 0.076 Uiso 1 1 calc R U . . .
H6B H 0.158202 0.421793 -0.139664 0.076 Uiso 1 1 calc R U . . .
H6C H 0.244167 0.499840 -0.189348 0.076 Uiso 1 1 calc R U . . .
C7 C 0.3418(8) 0.5709(9) 0.0331(8) 0.057(3) Uani 1 1 d . . . . .
H7A H 0.391659 0.548984 -0.023029 0.085 Uiso 1 1 calc R U . . .
H7B H 0.301355 0.498943 0.043097 0.085 Uiso 1 1 calc R U . . .
H7C H 0.390363 0.641837 0.108297 0.085 Uiso 1 1 calc R U . . .
C8 C 0.1601(6) 1.0055(7) 0.0042(6) 0.0301(18) Uani 1 1 d . . . . .
H8A H 0.095880 0.924000 -0.021768 0.036 Uiso 1 1 calc R U . . .
H8B H 0.126796 1.057915 -0.012654 0.036 Uiso 1 1 calc R U . . .
C9 C 0.2053(7) 1.0700(8) 0.1380(6) 0.040(2) Uani 1 1 d . . . . .
H9A H 0.233750 1.016283 0.157672 0.048 Uiso 1 1 calc R U . . .
H9B H 0.271004 1.151004 0.165916 0.048 Uiso 1 1 calc R U . . .
C10 C 0.3464(7) 1.1089(7) -0.0415(7) 0.041(2) Uani 1 1 d . . . . .
H10A H 0.406178 1.093894 -0.087094 0.062 Uiso 1 1 calc R U . . .
H10B H 0.383440 1.158228 0.041911 0.062 Uiso 1 1 calc R U . . .
H10C H 0.308528 1.154820 -0.062614 0.062 Uiso 1 1 calc R U . . .
C11 C 0.1930(7) 0.9118(7) -0.1969(6) 0.040(2) Uani 1 1 d . . . . .
H11A H 0.130091 0.833460 -0.214508 0.060 Uiso 1 1 calc R U . . .
H11B H 0.250148 0.893110 -0.245049 0.060 Uiso 1 1 calc R U . . .
H11C H 0.159864 0.963490 -0.213751 0.060 Uiso 1 1 calc R U . . .
C12 C 0.3085(7) 0.4193(7) 0.4687(6) 0.0298(18) Uani 1 1 d . . . . .
H12A H 0.332704 0.385227 0.393206 0.036 Uiso 1 1 calc R U . . .
H12B H 0.380470 0.468356 0.531512 0.036 Uiso 1 1 calc R U . . .
C13 C 0.2327(7) 0.3103(7) 0.4830(7) 0.0339(19) Uani 1 1 d . . . . .
H13A H 0.167692 0.251121 0.413593 0.041 Uiso 1 1 calc R U . . .
H13B H 0.198889 0.341390 0.552715 0.041 Uiso 1 1 calc R U . . .
C14 C 0.3133(7) 0.2439(7) 0.4972(6) 0.0307(18) Uani 1 1 d . . . . .
H14A H 0.382217 0.306938 0.561611 0.037 Uiso 1 1 calc R U . . .
H14B H 0.342235 0.209288 0.424703 0.037 Uiso 1 1 calc R U . . .
C15 C 0.1355(6) 0.4437(7) 0.3733(6) 0.0335(19) Uani 1 1 d . . . . .
H15A H 0.079695 0.374032 0.379987 0.040 Uiso 1 1 calc R U . . .
H15B H 0.097648 0.504480 0.385680 0.040 Uiso 1 1 calc R U . . .
C16 C 0.1568(7) 0.3915(8) 0.2492(7) 0.045(2) Uani 1 1 d . . . . .
H16A H 0.214869 0.458073 0.240349 0.054 Uiso 1 1 calc R U . . .
H16B H 0.186113 0.323136 0.230610 0.054 Uiso 1 1 calc R U . . .
C17 C 0.3388(7) 0.6167(7) 0.4647(7) 0.039(2) Uani 1 1 d . . . . .
H17A H 0.301486 0.670681 0.457780 0.059 Uiso 1 1 calc R U . . .
H17B H 0.371863 0.581865 0.396095 0.059 Uiso 1 1 calc R U . . .
H17C H 0.401602 0.665963 0.535291 0.059 Uiso 1 1 calc R U . . .
C18 C 0.2116(8) 0.5683(8) 0.5889(7) 0.043(2) Uani 1 1 d . . . . .
H18A H 0.278356 0.601479 0.652816 0.065 Uiso 1 1 calc R U . . .
H18B H 0.145803 0.504930 0.593061 0.065 Uiso 1 1 calc R U . . .
H18C H 0.188085 0.636568 0.595681 0.065 Uiso 1 1 calc R U . . .
C19 C 0.3410(7) 0.0738(8) 0.5258(7) 0.039(2) Uani 1 1 d . . . . .
H19A H 0.299527 -0.002604 0.530387 0.047 Uiso 1 1 calc R U . . .
H19B H 0.366595 0.046869 0.450845 0.047 Uiso 1 1 calc R U . . .
C20 C 0.4509(9) 0.1550(10) 0.6257(9) 0.064(3) Uani 1 1 d . . . . .
H20A H 0.514197 0.122951 0.601798 0.076 Uiso 1 1 calc R U . . .
H20B H 0.478007 0.241863 0.639431 0.076 Uiso 1 1 calc R U . . .
C21 C 0.2107(8) 0.1804(8) 0.6375(7) 0.047(2) Uani 1 1 d . . . . .
H21A H 0.144001 0.204244 0.629255 0.071 Uiso 1 1 calc R U . . .
H21B H 0.274789 0.252933 0.700125 0.071 Uiso 1 1 calc R U . . .
H21C H 0.186576 0.112832 0.656636 0.071 Uiso 1 1 calc R U . . .
C22 C 0.1476(8) 0.0372(8) 0.4229(7) 0.051(2) Uani 1 1 d . . . . .
H22A H 0.109704 -0.032272 0.437193 0.076 Uiso 1 1 calc R U . . .
H22B H 0.174596 0.005863 0.349740 0.076 Uiso 1 1 calc R U . . .
H22C H 0.091235 0.074705 0.417068 0.076 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'
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
C1 N1 C6 110.1(6) . .
C1 N1 C4 113.2(6) . .
C6 N1 C4 108.0(6) . .
C1 N1 C7 106.8(6) . .
C6 N1 C7 107.9(6) . .
C4 N1 C7 110.7(6) . .
C11 N2 C10 108.0(6) . .
C11 N2 C8 107.6(5) . .
C10 N2 C8 109.8(5) . .
C11 N2 C3 110.1(5) . .
C10 N2 C3 107.2(5) . .
C8 N2 C3 114.1(5) . .
C18 N3 C17 106.7(6) . .
C18 N3 C15 108.1(6) . .
C17 N3 C15 111.0(6) . .
C18 N3 C12 110.9(6) . .
C17 N3 C12 106.6(6) . .
C15 N3 C12 113.4(5) . .
C21 N4 C22 109.4(7) . .
C21 N4 C19 110.5(6) . .
C22 N4 C19 107.6(6) . .
C21 N4 C14 113.0(6) . .
C22 N4 C14 108.7(6) . .
C19 N4 C14 107.5(6) . .
C5 O1 H1 109.5 . .
C9 O2 H2 109.5 . .
C16 O3 H3 109.5 . .
C20 O4 H4 109.5 . .
N1 C1 C2 114.8(6) . .
N1 C1 H1A 108.6 . .
C2 C1 H1A 108.6 . .
N1 C1 H1B 108.6 . .
C2 C1 H1B 108.6 . .
H1A C1 H1B 107.6 . .
C3 C2 C1 108.4(6) . .
C3 C2 H2A 110.0 . .
C1 C2 H2A 110.0 . .
C3 C2 H2B 110.0 . .
C1 C2 H2B 110.0 . .
H2A C2 H2B 108.4 . .
N2 C3 C2 114.4(6) . .
N2 C3 H3A 108.7 . .
C2 C3 H3A 108.7 . .
N2 C3 H3B 108.7 . .
C2 C3 H3B 108.7 . .
H3A C3 H3B 107.6 . .
N1 C4 C5 117.2(7) . .
N1 C4 H4A 108.0 . .
C5 C4 H4A 108.0 . .
N1 C4 H4B 108.0 . .
C5 C4 H4B 108.0 . .
H4A C4 H4B 107.2 . .
O1 C5 C4 111.9(8) . .
O1 C5 H5A 109.2 . .
C4 C5 H5A 109.2 . .
O1 C5 H5B 109.2 . .
C4 C5 H5B 109.2 . .
H5A C5 H5B 107.9 . .
N1 C6 H6A 109.5 . .
N1 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
N1 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
N1 C7 H7A 109.5 . .
N1 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
N1 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
N2 C8 C9 114.7(6) . .
N2 C8 H8A 108.6 . .
C9 C8 H8A 108.6 . .
N2 C8 H8B 108.6 . .
C9 C8 H8B 108.6 . .
H8A C8 H8B 107.6 . .
O2 C9 C8 108.0(6) . .
O2 C9 H9A 110.1 . .
C8 C9 H9A 110.1 . .
O2 C9 H9B 110.1 . .
C8 C9 H9B 110.1 . .
H9A C9 H9B 108.4 . .
N2 C10 H10A 109.5 . .
N2 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
N2 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
N2 C11 H11A 109.5 . .
N2 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
N2 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C13 C12 N3 114.2(6) . .
C13 C12 H12A 108.7 . .
N3 C12 H12A 108.7 . .
C13 C12 H12B 108.7 . .
N3 C12 H12B 108.7 . .
H12A C12 H12B 107.6 . .
C12 C13 C14 107.2(6) . .
C12 C13 H13A 110.3 . .
C14 C13 H13A 110.3 . .
C12 C13 H13B 110.3 . .
C14 C13 H13B 110.3 . .
H13A C13 H13B 108.5 . .
C13 C14 N4 114.1(6) . .
C13 C14 H14A 108.7 . .
N4 C14 H14A 108.7 . .
C13 C14 H14B 108.7 . .
N4 C14 H14B 108.7 . .
H14A C14 H14B 107.6 . .
C16 C15 N3 115.3(6) . .
C16 C15 H15A 108.5 . .
N3 C15 H15A 108.5 . .
C16 C15 H15B 108.5 . .
N3 C15 H15B 108.5 . .
H15A C15 H15B 107.5 . .
O3 C16 C15 105.3(7) . .
O3 C16 H16A 110.7 . .
C15 C16 H16A 110.7 . .
O3 C16 H16B 110.7 . .
C15 C16 H16B 110.7 . .
H16A C16 H16B 108.8 . .
N3 C17 H17A 109.5 . .
N3 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
N3 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
N3 C18 H18A 109.5 . .
N3 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
N3 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C20 C19 N4 116.4(7) . .
C20 C19 H19A 108.2 . .
N4 C19 H19A 108.2 . .
C20 C19 H19B 108.2 . .
N4 C19 H19B 108.2 . .
H19A C19 H19B 107.3 . .
O4 C20 C19 112.8(8) . .
O4 C20 H20A 109.0 . .
C19 C20 H20A 109.0 . .
O4 C20 H20B 109.0 . .
C19 C20 H20B 109.0 . .
H20A C20 H20B 107.8 . .
N4 C21 H21A 109.5 . .
N4 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
N4 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
N4 C22 H22A 109.5 . .
N4 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
N4 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.491(9) .
N1 C6 1.503(9) .
N1 C4 1.506(10) .
N1 C7 1.517(9) .
N2 C11 1.499(8) .
N2 C10 1.507(9) .
N2 C8 1.508(8) .
N2 C3 1.522(8) .
N3 C18 1.496(9) .
N3 C17 1.512(10) .
N3 C15 1.520(9) .
N3 C12 1.527(8) .
N4 C21 1.490(9) .
N4 C22 1.493(10) .
N4 C19 1.520(9) .
N4 C14 1.532(9) .
O1 C5 1.387(10) .
O1 H1 0.8200 .
O2 C9 1.422(8) .
O2 H2 0.8200 .
O3 C16 1.398(9) .
O3 H3 0.8200 .
O4 C20 1.410(11) .
O4 H4 0.8200 .
C1 C2 1.538(10) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 C3 1.526(10) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C5 1.543(12) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 C9 1.519(10) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 C13 1.496(10) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C14 1.523(9) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 C16 1.500(10) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 C20 1.507(12) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 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
C22 H22A Br3 0.96 2.90 3.814(8) 160.0 1_545 yes
C19 H19B Br1 0.97 2.86 3.775(8) 158.5 . yes
C18 H18C Br3 0.96 3.09 3.947(8) 148.8 . yes
C17 H17C Br1 0.96 2.93 3.690(7) 137.4 2_666 yes
C17 H17B Br4 0.96 2.99 3.913(8) 160.7 . yes
C16 H16B O2 0.97 2.60 3.389(10) 138.8 1_545 yes
C15 H15B Br3 0.97 2.90 3.817(7) 158.3 . yes
C14 H14B Br1 0.97 3.05 3.933(7) 152.6 . yes
C14 H14A Br4 0.97 2.95 3.814(7) 149.4 2_666 yes
C13 H13B Br3 0.97 3.09 3.679(7) 120.3 2_566 yes
C13 H13A O2 0.97 2.53 3.380(9) 146.5 1_545 yes
C12 H12B Br4 0.97 2.87 3.740(7) 150.0 2_666 yes
C11 H11B Br1 0.96 3.08 3.950(8) 151.0 2_665 yes
C10 H10B Br4 0.96 3.01 3.779(7) 137.7 1_565 yes
C10 H10A Br1 0.96 2.99 3.879(8) 154.6 2_665 yes
C9 H9A Br1 0.97 3.10 3.788(8) 129.3 1_565 yes
C8 H8B Br2 0.97 2.89 3.835(7) 165.6 1_564 yes
C7 H7C O4 0.96 2.61 3.530(11) 161.1 2_666 yes
C7 H7A Br4 0.96 3.06 3.923(10) 150.6 2_665 yes
C6 H6C Br4 0.96 3.05 3.918(9) 151.6 2_665 yes
C6 H6B Br2 0.96 2.85 3.799(9) 170.7 1_554 yes
C5 H5B Br2 0.97 3.01 3.763(9) 135.0 2_566 yes
C3 H3B Br1 0.97 3.00 3.889(7) 153.2 2_665 yes
C3 H3A Br1 0.97 2.81 3.755(7) 165.0 1_565 yes
C1 H1B Br1 0.97 3.08 3.969(7) 152.3 1_565 yes
C1 H1A Br4 0.97 2.96 3.869(7) 156.6 2_665 yes
O4 H4 Br1 0.82 2.43 3.247(6) 173.0 2_656 yes
O3 H3 Br2 0.82 2.46 3.283(6) 179.6 1_554 yes
O2 H2 Br2 0.82 2.51 3.292(6) 160.4 2_566 yes
O1 H1 Br3 0.82 2.54 3.344(7) 167.1 . 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
C6 N1 C1 C2 66.5(8) . . . .
C4 N1 C1 C2 -54.5(8) . . . .
C7 N1 C1 C2 -176.6(6) . . . .
N1 C1 C2 C3 178.9(6) . . . .
C11 N2 C3 C2 -69.9(7) . . . .
C10 N2 C3 C2 172.9(6) . . . .
C8 N2 C3 C2 51.1(8) . . . .
C1 C2 C3 N2 -175.3(5) . . . .
C1 N1 C4 C5 -52.5(9) . . . .
C6 N1 C4 C5 -174.7(7) . . . .
C7 N1 C4 C5 67.4(9) . . . .
N1 C4 C5 O1 -86.7(10) . . . .
C11 N2 C8 C9 176.6(6) . . . .
C10 N2 C8 C9 -66.2(8) . . . .
C3 N2 C8 C9 54.2(8) . . . .
N2 C8 C9 O2 177.2(6) . . . .
C18 N3 C12 C13 60.6(8) . . . .
C17 N3 C12 C13 176.3(6) . . . .
C15 N3 C12 C13 -61.3(8) . . . .
N3 C12 C13 C14 -171.2(6) . . . .
C12 C13 C14 N4 175.2(6) . . . .
C21 N4 C14 C13 -62.0(8) . . . .
C22 N4 C14 C13 59.7(8) . . . .
C19 N4 C14 C13 175.9(6) . . . .
C18 N3 C15 C16 173.4(7) . . . .
C17 N3 C15 C16 56.7(8) . . . .
C12 N3 C15 C16 -63.2(9) . . . .
N3 C15 C16 O3 -175.6(6) . . . .
C21 N4 C19 C20 -57.3(9) . . . .
C22 N4 C19 C20 -176.7(7) . . . .
C14 N4 C19 C20 66.4(8) . . . .
N4 C19 C20 O4 82.3(9) . . . .
