#------------------------------------------------------------------------------
#$Date: 2019-11-11 19:23:16 +0200 (Mon, 11 Nov 2019) $
#$Revision: 227053 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/56/4035604.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_4035604
loop_
_publ_author_name
'Corradi, Silvia'
'Mazzoccanti, Giulia'
'Ghirga, Francesca'
'Quaglio, Deborah'
'Nevola, Laura'
'Massera, Chiara'
'Ugozzoli, Franco'
'Giannini, Giuseppe'
'Ciogli, Alessia'
'D'Acquarica, Ilaria'
_publ_section_title
;
 Synthesis of Bromoundecyl Resorc[4]arenes and Applications of the Cone
 Stereoisomer as Selector for Liquid Chromatography.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7683
_journal_page_last               7693
_journal_paper_doi               10.1021/acs.joc.8b00488
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C88 H132 Br4 O16'
_chemical_formula_sum            'C88 H132 Br4 O16'
_chemical_formula_weight         1765.57
_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-2014/7
_cell_angle_alpha                99.057(6)
_cell_angle_beta                 99.848(6)
_cell_angle_gamma                98.921(6)
_cell_formula_units_Z            1
_cell_length_a                   12.197(3)
_cell_length_b                   18.407(5)
_cell_length_c                   10.556(3)
_cell_measurement_reflns_used    2034
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.174
_cell_measurement_theta_min      1.725
_cell_volume                     2265.2(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_publication_material
'SHELXL and WINGX (Farrugia, J. App. Cryst.2012, 45, 849-854'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR97 (Giacovazzo et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'BRUKER AXS SMART 1000'
_diffrn_measurement_method       omega-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0947
_diffrn_reflns_av_unetI/netI     0.1941
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21784
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.174
_diffrn_reflns_theta_max         25.174
_diffrn_reflns_theta_min         1.725
_exptl_absorpt_coefficient_mu    1.837
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.749126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.676
_refine_diff_density_min         -1.095
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         8001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.2636
_refine_ls_R_factor_gt           0.1116
_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)+(0.1520P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2910
_refine_ls_wR_factor_ref         0.3495
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2431
_reflns_number_total             8001
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b00488_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4035604
_shelx_shelxl_version_number     2014/7
_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.
;
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
Br1A Br 0.8957(2) 0.77223(19) 0.5481(3) 0.2176(14) Uani 1 1 d . .
O1A O -0.2523(4) -0.0363(3) 0.7539(5) 0.0339(15) Uani 1 1 d . .
O2A O 0.1444(4) -0.0485(3) 0.8817(6) 0.0377(16) Uani 1 1 d . .
O3A O -0.1765(6) 0.2193(4) 0.8716(7) 0.0549(19) Uani 1 1 d . .
O4A O -0.0177(6) 0.2583(4) 0.8067(6) 0.059(2) Uani 1 1 d . .
C1A C 0.0025(6) 0.0773(5) 0.7148(7) 0.028(2) Uani 1 1 d . .
H1A H 0.0226 0.1191 0.6784 0.033 Uiso 1 1 calc R U
C2A C -0.1111(6) 0.0519(5) 0.7072(7) 0.0239(19) Uani 1 1 d . .
C3A C -0.1381(6) -0.0121(5) 0.7610(8) 0.029(2) Uani 1 1 d . .
C4A C -0.0560(7) -0.0456(5) 0.8186(8) 0.030(2) Uani 1 1 d . .
H4A H -0.0765 -0.0875 0.8544 0.036 Uiso 1 1 calc R U
C5A C 0.0572(7) -0.0182(5) 0.8247(8) 0.029(2) Uani 1 1 d . .
C6A C 0.0899(6) 0.0450(4) 0.7731(7) 0.0225(19) Uani 1 1 d . .
C7A C -0.2834(7) -0.0944(5) 0.8240(10) 0.049(3) Uani 1 1 d . .
H7A1 H -0.3645 -0.1063 0.8117 0.073 Uiso 1 1 calc R U
H7A2 H -0.2553 -0.1381 0.7918 0.073 Uiso 1 1 calc R U
H7A3 H -0.2514 -0.0775 0.9156 0.073 Uiso 1 1 calc R U
C8A C 0.1179(7) -0.1131(5) 0.9359(9) 0.045(3) Uani 1 1 d . .
H8A1 H 0.1867 -0.1281 0.9721 0.068 Uiso 1 1 calc R U
H8A2 H 0.0763 -0.1020 1.0036 0.068 Uiso 1 1 calc R U
H8A3 H 0.0728 -0.1529 0.8686 0.068 Uiso 1 1 calc R U
C9A C -0.2027(6) 0.0921(4) 0.6513(7) 0.0250(19) Uani 1 1 d . .
H9A H -0.2590 0.0899 0.7073 0.030 Uiso 1 1 calc R U
C10A C -0.1604(6) 0.1753(4) 0.6526(8) 0.027(2) Uani 1 1 d . .
H10A H -0.0981 0.1801 0.6065 0.033 Uiso 1 1 calc R U
H10B H -0.2209 0.1957 0.6069 0.033 Uiso 1 1 calc R U
C11A C -0.1220(8) 0.2186(5) 0.7884(10) 0.038(2) Uani 1 1 d . .
C12A C 0.0281(9) 0.3034(7) 0.9384(11) 0.075(4) Uani 1 1 d . .
H12A H 0.0257 0.2718 1.0036 0.090 Uiso 1 1 calc R U
H12B H -0.0169 0.3414 0.9568 0.090 Uiso 1 1 calc R U
C13A C 0.1495(10) 0.3401(7) 0.9435(13) 0.085(4) Uani 1 1 d . .
H13A H 0.1802 0.3687 1.0311 0.102 Uiso 1 1 calc R U
H13B H 0.1931 0.3008 0.9290 0.102 Uiso 1 1 calc R U
C14A C 0.1667(10) 0.3896(8) 0.8500(13) 0.082(4) Uani 1 1 d . .
H14A H 0.1237 0.4294 0.8635 0.099 Uiso 1 1 calc R U
H14B H 0.1381 0.3614 0.7617 0.099 Uiso 1 1 calc R U
C15A C 0.2878(11) 0.4232(7) 0.8636(15) 0.095(4) Uani 1 1 d . .
H15A H 0.3161 0.4499 0.9530 0.114 Uiso 1 1 calc R U
H15B H 0.3297 0.3831 0.8490 0.114 Uiso 1 1 calc R U
C16A C 0.3117(12) 0.4756(9) 0.7738(17) 0.120(6) Uani 1 1 d . .
H16A H 0.2675 0.5146 0.7875 0.143 Uiso 1 1 calc R U
H16B H 0.2833 0.4482 0.6848 0.143 Uiso 1 1 calc R U
C17A C 0.4335(12) 0.5136(8) 0.7826(17) 0.108(5) Uani 1 1 d . .
H17A H 0.4609 0.5427 0.8704 0.130 Uiso 1 1 calc R U
H17B H 0.4783 0.4746 0.7726 0.130 Uiso 1 1 calc R U
C18A C 0.4566(13) 0.5611(10) 0.6936(17) 0.117(5) Uani 1 1 d . .
H18A H 0.4120 0.6002 0.7024 0.140 Uiso 1 1 calc R U
H18B H 0.4316 0.5322 0.6054 0.140 Uiso 1 1 calc R U
C19A C 0.5774(14) 0.5971(9) 0.7102(16) 0.116(6) Uani 1 1 d . .
H19A H 0.6017 0.6272 0.7976 0.139 Uiso 1 1 calc R U
H19B H 0.6223 0.5580 0.7042 0.139 Uiso 1 1 calc R U
C20A C 0.6021(15) 0.6442(13) 0.617(2) 0.165(8) Uani 1 1 d . .
H20A H 0.5560 0.6826 0.6227 0.198 Uiso 1 1 calc R U
H20B H 0.5768 0.6136 0.5297 0.198 Uiso 1 1 calc R U
C21A C 0.7273(15) 0.6841(9) 0.6276(18) 0.131(6) Uani 1 1 d . .
H21A H 0.7745 0.6462 0.6256 0.157 Uiso 1 1 calc R U
H21B H 0.7517 0.7171 0.7124 0.157 Uiso 1 1 calc R U
C22A C 0.7493(12) 0.7290(10) 0.5249(18) 0.133(7) Uani 1 1 d . .
H22A H 0.7034 0.7675 0.5265 0.159 Uiso 1 1 calc R U
H22B H 0.7266 0.6965 0.4395 0.159 Uiso 1 1 calc R U
Br1B Br 1.40383(16) 0.77581(11) 0.79355(19) 0.1323(9) Uani 1 1 d . .
O1B O 0.4358(4) 0.0583(3) 0.8581(6) 0.0390(16) Uani 1 1 d . .
O2B O 0.4173(4) -0.1108(3) 0.4522(5) 0.0339(15) Uani 1 1 d . .
O3B O 0.3666(5) 0.2128(4) 0.9775(7) 0.0564(19) Uani 1 1 d . .
O4B O 0.4186(5) 0.2310(3) 0.7913(6) 0.0453(17) Uani 1 1 d . .
C1B C 0.2168(6) -0.0077(4) 0.5723(8) 0.025(2) Uani 1 1 d . .
H1B H 0.1434 -0.0010 0.5427 0.031 Uiso 1 1 calc R U
C2B C 0.2714(6) 0.0276(4) 0.6963(8) 0.026(2) Uani 1 1 d . .
C3B C 0.3828(7) 0.0197(5) 0.7393(8) 0.031(2) Uani 1 1 d . .
C4B C 0.4328(7) -0.0271(5) 0.6576(9) 0.035(2) Uani 1 1 d . .
H4B H 0.5060 -0.0344 0.6868 0.042 Uiso 1 1 calc R U
C5B C 0.3741(6) -0.0624(5) 0.5342(8) 0.029(2) Uani 1 1 d . .
C6B C 0.2655(6) -0.0530(4) 0.4888(8) 0.026(2) Uani 1 1 d . .
C7B C 0.5562(7) 0.0636(6) 0.8981(10) 0.061(3) Uani 1 1 d . .
H7B1 H 0.5814 0.0929 0.9849 0.092 Uiso 1 1 calc R U
H7B2 H 0.5730 0.0143 0.8973 0.092 Uiso 1 1 calc R U
H7B3 H 0.5944 0.0872 0.8387 0.092 Uiso 1 1 calc R U
C8B C 0.5271(6) -0.1284(5) 0.4972(9) 0.036(2) Uani 1 1 d . .
H8B1 H 0.5454 -0.1627 0.4291 0.054 Uiso 1 1 calc R U
H8B2 H 0.5833 -0.0833 0.5191 0.054 Uiso 1 1 calc R U
H8B3 H 0.5255 -0.1509 0.5731 0.054 Uiso 1 1 calc R U
C9B C 0.2160(6) 0.0761(4) 0.7879(8) 0.027(2) Uani 1 1 d . .
H9B H 0.2518 0.0736 0.8772 0.033 Uiso 1 1 calc R U
C10B C 0.2416(6) 0.1592(5) 0.7755(9) 0.037(2) Uani 1 1 d . .
H10C H 0.2458 0.1617 0.6853 0.045 Uiso 1 1 calc R U
H10D H 0.1791 0.1825 0.7959 0.045 Uiso 1 1 calc R U
C11B C 0.3473(7) 0.2024(5) 0.8609(10) 0.037(2) Uani 1 1 d . .
C12B C 0.5244(7) 0.2793(6) 0.8654(9) 0.051(3) Uani 1 1 d . .
H12C H 0.5696 0.2506 0.9153 0.061 Uiso 1 1 calc R U
H12D H 0.5079 0.3196 0.9260 0.061 Uiso 1 1 calc R U
C13B C 0.5871(8) 0.3103(6) 0.7724(10) 0.058(3) Uani 1 1 d . .
H13C H 0.5351 0.3292 0.7111 0.070 Uiso 1 1 calc R U
H13D H 0.6138 0.2700 0.7228 0.070 Uiso 1 1 calc R U
C14B C 0.6868(8) 0.3722(6) 0.8338(11) 0.059(3) Uani 1 1 d . .
H14C H 0.6600 0.4131 0.8814 0.071 Uiso 1 1 calc R U
H14D H 0.7380 0.3538 0.8968 0.071 Uiso 1 1 calc R U
C15B C 0.7527(9) 0.4024(6) 0.7371(12) 0.069(3) Uani 1 1 d . .
H15C H 0.7858 0.3627 0.6953 0.083 Uiso 1 1 calc R U
H15D H 0.7005 0.4167 0.6694 0.083 Uiso 1 1 calc R U
C16B C 0.8441(8) 0.4677(6) 0.7977(11) 0.060(3) Uani 1 1 d . .
H16C H 0.8971 0.4535 0.8648 0.072 Uiso 1 1 calc R U
H16D H 0.8114 0.5075 0.8398 0.072 Uiso 1 1 calc R U
C17B C 0.9086(10) 0.4974(6) 0.6984(11) 0.072(3) Uani 1 1 d . .
H17C H 0.9457 0.4587 0.6612 0.086 Uiso 1 1 calc R U
H17D H 0.8546 0.5078 0.6279 0.086 Uiso 1 1 calc R U
C18B C 0.9970(10) 0.5679(6) 0.7559(12) 0.071(3) Uani 1 1 d . .
H18C H 0.9602 0.6061 0.7957 0.085 Uiso 1 1 calc R U
H18D H 1.0522 0.5571 0.8247 0.085 Uiso 1 1 calc R U
C19B C 1.0581(9) 0.5987(6) 0.6582(11) 0.070(3) Uani 1 1 d . .
H19C H 1.0027 0.6081 0.5880 0.084 Uiso 1 1 calc R U
H19D H 1.0970 0.5612 0.6205 0.084 Uiso 1 1 calc R U
C20B C 1.1458(9) 0.6724(6) 0.7171(12) 0.073(4) Uani 1 1 d . .
H20C H 1.1076 0.7090 0.7592 0.088 Uiso 1 1 calc R U
H20D H 1.2034 0.6623 0.7840 0.088 Uiso 1 1 calc R U
C21B C 1.2009(10) 0.7048(7) 0.6213(12) 0.085(4) Uani 1 1 d . .
H21C H 1.1429 0.7108 0.5506 0.103 Uiso 1 1 calc R U
H21D H 1.2442 0.6698 0.5846 0.103 Uiso 1 1 calc R U
C22B C 1.2795(10) 0.7800(8) 0.6753(14) 0.099(5) Uani 1 1 d . .
H22C H 1.2374 0.8144 0.7162 0.119 Uiso 1 1 calc R U
H22D H 1.3037 0.8002 0.6029 0.119 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'
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
C3A O1A C7A 117.1(6) . .
C5A O2A C8A 118.5(6) . .
C11A O4A C12A 115.8(8) . .
C6A C1A C2A 124.8(8) . .
C6A C1A H1A 117.6 . .
C2A C1A H1A 117.6 . .
C1A C2A C3A 115.9(7) . .
C1A C2A C9A 122.9(7) . .
C3A C2A C9A 121.1(7) . .
O1A C3A C4A 123.5(8) . .
O1A C3A C2A 115.0(7) . .
C4A C3A C2A 121.4(7) . .
C5A C4A C3A 121.0(8) . .
C5A C4A H4A 119.5 . .
C3A C4A H4A 119.5 . .
O2A C5A C4A 124.3(8) . .
O2A C5A C6A 115.2(7) . .
C4A C5A C6A 120.5(7) . .
C1A C6A C5A 116.3(7) . .
C1A C6A C9B 124.6(7) . .
C5A C6A C9B 119.1(7) . .
O1A C7A H7A1 109.5 . .
O1A C7A H7A2 109.5 . .
H7A1 C7A H7A2 109.5 . .
O1A C7A H7A3 109.5 . .
H7A1 C7A H7A3 109.5 . .
H7A2 C7A H7A3 109.5 . .
O2A C8A H8A1 109.5 . .
O2A C8A H8A2 109.5 . .
H8A1 C8A H8A2 109.5 . .
O2A C8A H8A3 109.5 . .
H8A1 C8A H8A3 109.5 . .
H8A2 C8A H8A3 109.5 . .
C2A C9A C6B 112.6(7) . 2_556
C2A C9A C10A 114.0(6) . .
C6B C9A C10A 109.3(6) 2_556 .
C2A C9A H9A 106.8 . .
C6B C9A H9A 106.8 2_556 .
C10A C9A H9A 106.8 . .
C11A C10A C9A 111.4(7) . .
C11A C10A H10A 109.3 . .
C9A C10A H10A 109.3 . .
C11A C10A H10B 109.3 . .
C9A C10A H10B 109.3 . .
H10A C10A H10B 108.0 . .
O3A C11A O4A 123.1(9) . .
O3A C11A C10A 125.3(9) . .
O4A C11A C10A 111.6(9) . .
O4A C12A C13A 108.3(9) . .
O4A C12A H12A 110.0 . .
C13A C12A H12A 110.0 . .
O4A C12A H12B 110.0 . .
C13A C12A H12B 110.0 . .
H12A C12A H12B 108.4 . .
C14A C13A C12A 116.4(11) . .
C14A C13A H13A 108.2 . .
C12A C13A H13A 108.2 . .
C14A C13A H13B 108.2 . .
C12A C13A H13B 108.2 . .
H13A C13A H13B 107.3 . .
C13A C14A C15A 112.3(12) . .
C13A C14A H14A 109.2 . .
C15A C14A H14A 109.2 . .
C13A C14A H14B 109.2 . .
C15A C14A H14B 109.2 . .
H14A C14A H14B 107.9 . .
C16A C15A C14A 115.4(13) . .
C16A C15A H15A 108.4 . .
C14A C15A H15A 108.4 . .
C16A C15A H15B 108.4 . .
C14A C15A H15B 108.4 . .
H15A C15A H15B 107.5 . .
C15A C16A C17A 118.9(14) . .
C15A C16A H16A 107.6 . .
C17A C16A H16A 107.6 . .
C15A C16A H16B 107.6 . .
C17A C16A H16B 107.6 . .
H16A C16A H16B 107.0 . .
C18A C17A C16A 118.8(14) . .
C18A C17A H17A 107.6 . .
C16A C17A H17A 107.6 . .
C18A C17A H17B 107.6 . .
C16A C17A H17B 107.6 . .
H17A C17A H17B 107.1 . .
C17A C18A C19A 115.4(14) . .
C17A C18A H18A 108.4 . .
C19A C18A H18A 108.4 . .
C17A C18A H18B 108.4 . .
C19A C18A H18B 108.4 . .
H18A C18A H18B 107.5 . .
C20A C19A C18A 115.6(16) . .
C20A C19A H19A 108.4 . .
C18A C19A H19A 108.4 . .
C20A C19A H19B 108.4 . .
C18A C19A H19B 108.4 . .
H19A C19A H19B 107.4 . .
C19A C20A C21A 118.8(16) . .
C19A C20A H20A 107.6 . .
C21A C20A H20A 107.6 . .
C19A C20A H20B 107.6 . .
C21A C20A H20B 107.6 . .
H20A C20A H20B 107.1 . .
C20A C21A C22A 116.7(16) . .
C20A C21A H21A 108.1 . .
C22A C21A H21A 108.1 . .
C20A C21A H21B 108.1 . .
C22A C21A H21B 108.1 . .
H21A C21A H21B 107.3 . .
C21A C22A Br1A 112.6(12) . .
C21A C22A H22A 109.1 . .
Br1A C22A H22A 109.1 . .
C21A C22A H22B 109.1 . .
Br1A C22A H22B 109.1 . .
H22A C22A H22B 107.8 . .
C3B O1B C7B 119.4(7) . .
C5B O2B C8B 119.4(6) . .
C11B O4B C12B 116.6(7) . .
C6B C1B C2B 123.3(7) . .
C6B C1B H1B 118.3 . .
C2B C1B H1B 118.3 . .
C1B C2B C3B 118.4(8) . .
C1B C2B C9B 122.7(7) . .
C3B C2B C9B 118.9(7) . .
O1B C3B C4B 124.0(7) . .
O1B C3B C2B 116.8(8) . .
C4B C3B C2B 119.2(8) . .
C5B C4B C3B 120.4(8) . .
C5B C4B H4B 119.8 . .
C3B C4B H4B 119.8 . .
O2B C5B C4B 122.8(7) . .
O2B C5B C6B 116.2(7) . .
C4B C5B C6B 121.0(8) . .
C5B C6B C1B 117.6(8) . .
C5B C6B C9A 119.8(8) . 2_556
C1B C6B C9A 122.6(7) . 2_556
O1B C7B H7B1 109.5 . .
O1B C7B H7B2 109.5 . .
H7B1 C7B H7B2 109.5 . .
O1B C7B H7B3 109.5 . .
H7B1 C7B H7B3 109.5 . .
H7B2 C7B H7B3 109.5 . .
O2B C8B H8B1 109.5 . .
O2B C8B H8B2 109.5 . .
H8B1 C8B H8B2 109.5 . .
O2B C8B H8B3 109.5 . .
H8B1 C8B H8B3 109.5 . .
H8B2 C8B H8B3 109.5 . .
C6A C9B C2B 112.1(6) . .
C6A C9B C10B 113.6(6) . .
C2B C9B C10B 111.5(7) . .
C6A C9B H9B 106.4 . .
C2B C9B H9B 106.4 . .
C10B C9B H9B 106.4 . .
C11B C10B C9B 114.4(7) . .
C11B C10B H10C 108.7 . .
C9B C10B H10C 108.7 . .
C11B C10B H10D 108.7 . .
C9B C10B H10D 108.7 . .
H10C C10B H10D 107.6 . .
O3B C11B O4B 123.6(8) . .
O3B C11B C10B 125.1(9) . .
O4B C11B C10B 111.3(8) . .
O4B C12B C13B 108.6(8) . .
O4B C12B H12C 110.0 . .
C13B C12B H12C 110.0 . .
O4B C12B H12D 110.0 . .
C13B C12B H12D 110.0 . .
H12C C12B H12D 108.4 . .
C12B C13B C14B 115.1(9) . .
C12B C13B H13C 108.5 . .
C14B C13B H13C 108.5 . .
C12B C13B H13D 108.5 . .
C14B C13B H13D 108.5 . .
H13C C13B H13D 107.5 . .
C15B C14B C13B 114.6(9) . .
C15B C14B H14C 108.6 . .
C13B C14B H14C 108.6 . .
C15B C14B H14D 108.6 . .
C13B C14B H14D 108.6 . .
H14C C14B H14D 107.6 . .
C16B C15B C14B 113.8(10) . .
C16B C15B H15C 108.8 . .
C14B C15B H15C 108.8 . .
C16B C15B H15D 108.8 . .
C14B C15B H15D 108.8 . .
H15C C15B H15D 107.7 . .
C15B C16B C17B 112.8(10) . .
C15B C16B H16C 109.0 . .
C17B C16B H16C 109.0 . .
C15B C16B H16D 109.0 . .
C17B C16B H16D 109.0 . .
H16C C16B H16D 107.8 . .
C18B C17B C16B 114.0(10) . .
C18B C17B H17C 108.8 . .
C16B C17B H17C 108.8 . .
C18B C17B H17D 108.8 . .
C16B C17B H17D 108.8 . .
H17C C17B H17D 107.7 . .
C19B C18B C17B 114.3(10) . .
C19B C18B H18C 108.7 . .
C17B C18B H18C 108.7 . .
C19B C18B H18D 108.7 . .
C17B C18B H18D 108.7 . .
H18C C18B H18D 107.6 . .
C18B C19B C20B 113.9(10) . .
C18B C19B H19C 108.8 . .
C20B C19B H19C 108.8 . .
C18B C19B H19D 108.8 . .
C20B C19B H19D 108.8 . .
H19C C19B H19D 107.7 . .
C21B C20B C19B 114.1(10) . .
C21B C20B H20C 108.7 . .
C19B C20B H20C 108.7 . .
C21B C20B H20D 108.7 . .
C19B C20B H20D 108.7 . .
H20C C20B H20D 107.6 . .
C20B C21B C22B 114.7(11) . .
C20B C21B H21C 108.6 . .
C22B C21B H21C 108.6 . .
C20B C21B H21D 108.6 . .
C22B C21B H21D 108.6 . .
H21C C21B H21D 107.6 . .
C21B C22B Br1B 114.1(9) . .
C21B C22B H22C 108.7 . .
Br1B C22B H22C 108.7 . .
C21B C22B H22D 108.7 . .
Br1B C22B H22D 108.7 . .
H22C C22B H22D 107.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1A C22A 1.798(14) .
O1A C3A 1.380(9) .
O1A C7A 1.434(10) .
O2A C5A 1.369(9) .
O2A C8A 1.415(10) .
O3A C11A 1.189(10) .
O4A C11A 1.331(10) .
O4A C12A 1.470(11) .
C1A C6A 1.399(10) .
C1A C2A 1.376(10) .
C1A H1A 0.9300 .
C2A C3A 1.404(11) .
C2A C9A 1.521(10) .
C3A C4A 1.361(11) .
C4A C5A 1.382(11) .
C4A H4A 0.9300 .
C5A C6A 1.392(11) .
C6A C9B 1.527(10) .
C7A H7A1 0.9600 .
C7A H7A2 0.9600 .
C7A H7A3 0.9600 .
C8A H8A1 0.9600 .
C8A H8A2 0.9600 .
C8A H8A3 0.9600 .
C9A C6B 1.548(11) 2_556
C9A C10A 1.536(11) .
C9A H9A 0.9800 .
C10A C11A 1.485(12) .
C10A H10A 0.9700 .
C10A H10B 0.9700 .
C12A C13A 1.517(15) .
C12A H12A 0.9700 .
C12A H12B 0.9700 .
C13A C14A 1.465(16) .
C13A H13A 0.9700 .
C13A H13B 0.9700 .
C14A C15A 1.483(16) .
C14A H14A 0.9700 .
C14A H14B 0.9700 .
C15A C16A 1.486(19) .
C15A H15A 0.9700 .
C15A H15B 0.9700 .
C16A C17A 1.522(18) .
C16A H16A 0.9700 .
C16A H16B 0.9700 .
C17A C18A 1.415(19) .
C17A H17A 0.9700 .
C17A H17B 0.9700 .
C18A C19A 1.487(18) .
C18A H18A 0.9700 .
C18A H18B 0.9700 .
C19A C20A 1.45(2) .
C19A H19A 0.9700 .
C19A H19B 0.9700 .
C20A C21A 1.57(2) .
C20A H20A 0.9700 .
C20A H20B 0.9700 .
C21A C22A 1.497(19) .
C21A H21A 0.9700 .
C21A H21B 0.9700 .
C22A H22A 0.9700 .
C22A H22B 0.9700 .
Br1B C22B 1.812(11) .
O1B C3B 1.340(10) .
O1B C7B 1.441(9) .
O2B C5B 1.370(9) .
O2B C8B 1.445(9) .
O3B C11B 1.191(10) .
O4B C11B 1.331(10) .
O4B C12B 1.465(10) .
C1B C6B 1.388(11) .
C1B C2B 1.371(11) .
C1B H1B 0.9300 .
C2B C3B 1.395(10) .
C2B C9B 1.525(11) .
C3B C4B 1.402(11) .
C4B C5B 1.380(11) .
C4B H4B 0.9300 .
C5B C6B 1.376(10) .
C6B C9A 1.548(11) 2_556
C7B H7B1 0.9600 .
C7B H7B2 0.9600 .
C7B H7B3 0.9600 .
C8B H8B1 0.9600 .
C8B H8B2 0.9600 .
C8B H8B3 0.9600 .
C9B C10B 1.544(11) .
C9B H9B 0.9800 .
C10B C11B 1.472(11) .
C10B H10C 0.9700 .
C10B H10D 0.9700 .
C12B C13B 1.474(13) .
C12B H12C 0.9700 .
C12B H12D 0.9700 .
C13B C14B 1.504(12) .
C13B H13C 0.9700 .
C13B H13D 0.9700 .
C14B C15B 1.523(14) .
C14B H14C 0.9700 .
C14B H14D 0.9700 .
C15B C16B 1.482(13) .
C15B H15C 0.9700 .
C15B H15D 0.9700 .
C16B C17B 1.531(14) .
C16B H16C 0.9700 .
C16B H16D 0.9700 .
C17B C18B 1.520(14) .
C17B H17C 0.9700 .
C17B H17D 0.9700 .
C18B C19B 1.502(14) .
C18B H18C 0.9700 .
C18B H18D 0.9700 .
C19B C20B 1.558(14) .
C19B H19C 0.9700 .
C19B H19D 0.9700 .
C20B C21B 1.458(14) .
C20B H20C 0.9700 .
C20B H20D 0.9700 .
C21B C22B 1.522(16) .
C21B H21C 0.9700 .
C21B H21D 0.9700 .
C22B H22C 0.9700 .
C22B H22D 0.9700 .
