#------------------------------------------------------------------------------
#$Date: 2021-03-05 03:48:56 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262588 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/22/7242212.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_7242212
loop_
_publ_author_name
'Hyodo, Tadashi'
'Tominaga, Masahide'
'Yamaguchi, Kentaro'
_publ_section_title
;
 Guest-dependent single-crystal-to-single-crystal transformations in
 porous adamantane-bearing macrocycles
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              1539
_journal_page_last               1543
_journal_paper_doi               10.1039/D0CE01782E
_journal_volume                  23
_journal_year                    2021
_chemical_formula_sum            'C52 H50 Br4 N8 O5'
_chemical_formula_weight         1186.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-07-07 deposited with the CCDC.	2021-01-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.890(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.1540(15)
_cell_length_b                   7.1493(7)
_cell_length_c                   23.597(2)
_cell_measurement_reflns_used    9742
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.44
_cell_measurement_theta_min      3.61
_cell_volume                     2645.5(4)
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.24
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            37077
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.725
_diffrn_reflns_theta_min         3.009
_diffrn_source                   'rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    4.144
_exptl_absorpt_correction_T_max  0.9403
_exptl_absorpt_correction_T_min  0.8968
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1196
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         1.588
_refine_diff_density_min         -1.116
_refine_diff_density_rms         0.211
_refine_ls_extinction_coef       0.0020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         5527
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0461
_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)+(0.0877P)²+3.0103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1361
_refine_ls_wR_factor_ref         0.1412
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5170
_reflns_number_total             5527
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01782e2.cif
_cod_data_source_block           1b
_cod_depositor_comments
'Adding full bibliography for 7242212--7242215.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7242212
_shelx_shelxl_version_number     2018/3
_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   0.682
_shelx_estimated_absorpt_t_max   0.820
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1A C 0.6276(14) 0.898(2) 0.5308(10) 0.202(9) Uani 0.5008(10) 1 d D U P A -1
H1A1 H 0.677918 0.870321 0.563035 0.242 Uiso 0.5008(10) 1 calc R U P A -1
H1A2 H 0.583160 0.950797 0.548592 0.242 Uiso 0.5008(10) 1 calc R U P A -1
C2A C 0.6526(9) 1.046(3) 0.4929(8) 0.159(7) Uani 0.5008(10) 1 d D U P A -1
H2AA H 0.681837 1.148060 0.517503 0.238 Uiso 0.5008(10) 1 calc R U P A -1
H2AB H 0.601451 1.094526 0.465788 0.238 Uiso 0.5008(10) 1 calc R U P A -1
H2AC H 0.690957 0.991870 0.470800 0.238 Uiso 0.5008(10) 1 calc R U P A -1
C3A C 0.556(2) 0.634(4) 0.4955(12) 0.317(15) Uani 0.5008(10) 1 d D U P A -1
H3A1 H 0.506012 0.677221 0.509692 0.380 Uiso 0.5008(10) 1 calc R U P A -1
H3A2 H 0.581128 0.531100 0.522125 0.380 Uiso 0.5008(10) 1 calc R U P A -1
C4A C 0.5149(17) 0.533(5) 0.4381(12) 0.264(16) Uani 0.5008(10) 1 d D U P A -1
H4AA H 0.460071 0.479171 0.440545 0.396 Uiso 0.5008(10) 1 calc R U P A -1
H4AB H 0.552900 0.432673 0.431403 0.396 Uiso 0.5008(10) 1 calc R U P A -1
H4AC H 0.505845 0.622238 0.405698 0.396 Uiso 0.5008(10) 1 calc R U P A -1
O1A O 0.5998(13) 0.743(2) 0.5067(11) 0.313(11) Uani 0.5008(10) 1 d D U P A -1
C1 C 0.77864(17) 0.1931(4) 0.68926(11) 0.0280(5) Uani 1 1 d . . . . .
C2 C 0.83903(16) 0.2682(4) 0.61009(11) 0.0284(5) Uani 1 1 d . . . . .
C3 C 0.86870(17) 0.1543(4) 0.57215(11) 0.0285(5) Uani 1 1 d . . . . .
C4 C 0.86839(17) 0.2169(4) 0.51621(11) 0.0284(5) Uani 1 1 d . . . . .
H4 H 0.889370 0.138024 0.490403 0.034 Uiso 1 1 calc R U . . .
C5 C 0.83759(17) 0.3940(4) 0.49783(11) 0.0268(5) Uani 1 1 d . . . . .
C6 C 0.80632(17) 0.5047(4) 0.53698(11) 0.0300(5) Uani 1 1 d . . . . .
H6 H 0.783192 0.624272 0.524735 0.036 Uiso 1 1 calc R U . . .
C7 C 0.80816(18) 0.4448(4) 0.59301(11) 0.0315(6) Uani 1 1 d . . . . .
H7 H 0.788473 0.523880 0.619353 0.038 Uiso 1 1 calc R U . . .
C8 C 0.83901(16) 0.4723(4) 0.43776(10) 0.0261(5) Uani 1 1 d . . . . .
C9 C 0.87382(18) 0.3322(4) 0.39988(11) 0.0324(6) Uani 1 1 d . . . . .
H9A H 0.837121 0.219596 0.393191 0.039 Uiso 1 1 calc R U . . .
H9B H 0.932029 0.293156 0.420563 0.039 Uiso 1 1 calc R U . . .
C10 C 0.87628(19) 0.4206(5) 0.34085(12) 0.0363(7) Uani 1 1 d . . . . .
H10 H 0.898946 0.327203 0.316871 0.044 Uiso 1 1 calc R U . . .
C11 C 0.78563(18) 0.4766(5) 0.30869(11) 0.0334(6) Uani 1 1 d . . . . .
H11A H 0.749046 0.363774 0.301442 0.040 Uiso 1 1 calc R U . . .
H11B H 0.786667 0.532182 0.270444 0.040 Uiso 1 1 calc R U . . .
C12 C 0.74782(17) 0.6187(4) 0.34469(11) 0.0264(5) Uani 1 1 d . . . . .
C13 C 0.74792(16) 0.5287(4) 0.40452(10) 0.0255(5) Uani 1 1 d . . . . .
H13A H 0.724243 0.618699 0.428368 0.031 Uiso 1 1 calc R U . . .
H13B H 0.710906 0.416559 0.398268 0.031 Uiso 1 1 calc R U . . .
C14 C 0.89634(17) 0.6486(4) 0.44588(11) 0.0311(6) Uani 1 1 d . . . . .
H14A H 0.874262 0.741982 0.469524 0.037 Uiso 1 1 calc R U . . .
H14B H 0.954942 0.614443 0.467192 0.037 Uiso 1 1 calc R U . . .
C15 C 0.93381(19) 0.5932(5) 0.35039(14) 0.0411(7) Uani 1 1 d . . . . .
H15A H 0.992529 0.557452 0.370984 0.049 Uiso 1 1 calc R U . . .
H15B H 0.935727 0.648809 0.312296 0.049 Uiso 1 1 calc R U . . .
C16 C 0.80722(17) 0.7906(4) 0.35559(12) 0.0318(6) Uani 1 1 d . . . . .
H16A H 0.807379 0.850885 0.317841 0.038 Uiso 1 1 calc R U . . .
H16B H 0.785447 0.882597 0.379847 0.038 Uiso 1 1 calc R U . . .
C17 C 0.89851(18) 0.7347(5) 0.38656(12) 0.0352(6) Uani 1 1 d . . . . .
H17 H 0.935642 0.848375 0.392919 0.042 Uiso 1 1 calc R U . . .
C18 C 0.65655(17) 0.1847(4) 0.73806(11) 0.0305(6) Uani 1 1 d . . . . .
C19 C 0.51250(17) 0.2368(5) 0.73734(11) 0.0340(6) Uani 1 1 d . . . . .
C20 C 0.46027(19) 0.1079(4) 0.70267(14) 0.0359(6) Uani 1 1 d . . . . .
C21 C 0.37618(18) 0.1538(4) 0.67702(13) 0.0337(6) Uani 1 1 d . . . . .
H21 H 0.340381 0.064477 0.653188 0.040 Uiso 1 1 calc R U . . .
C22 C 0.34364(16) 0.3277(4) 0.68560(11) 0.0280(5) Uani 1 1 d . . . . .
C23 C 0.39832(18) 0.4555(5) 0.72045(12) 0.0326(6) Uani 1 1 d . . . . .
H23 H 0.377406 0.576036 0.726712 0.039 Uiso 1 1 calc R U . . .
C24 C 0.48234(19) 0.4111(5) 0.74617(13) 0.0359(6) Uani 1 1 d . . . . .
H24 H 0.518699 0.500264 0.769660 0.043 Uiso 1 1 calc R U . . .
N1 N 0.79657(16) 0.1323(4) 0.74457(11) 0.0340(5) Uani 1 1 d . . . . .
N2 N 0.70234(15) 0.2328(4) 0.65586(10) 0.0332(5) Uani 1 1 d . . . . .
N3 N 0.63770(14) 0.2294(4) 0.68173(10) 0.0337(5) Uani 1 1 d . . . . .
N4 N 0.73196(16) 0.1270(4) 0.77005(10) 0.0357(6) Uani 1 1 d . . . . .
O1 O 0.84798(12) 0.2043(3) 0.66762(8) 0.0330(4) Uani 1 1 d . . . . .
O2 O 0.59555(12) 0.1888(4) 0.76798(8) 0.0388(5) Uani 1 1 d . . . . .
Br1 Br 0.90915(2) -0.08728(4) 0.59621(2) 0.03766(15) Uani 1 1 d . . . . .
Br2 Br 0.50322(2) -0.12905(6) 0.69065(2) 0.05493(16) Uani 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
O1A C1A C2A 117.6(15) . . ?
O1A C1A H1A1 107.9 . . ?
C2A C1A H1A1 107.9 . . ?
O1A C1A H1A2 107.9 . . ?
C2A C1A H1A2 107.9 . . ?
H1A1 C1A H1A2 107.2 . . ?
C1A C2A H2AA 109.5 . . ?
C1A C2A H2AB 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
C1A C2A H2AC 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
O1A C3A C4A 134(3) . . ?
O1A C3A H3A1 103.7 . . ?
C4A C3A H3A1 103.7 . . ?
O1A C3A H3A2 103.7 . . ?
C4A C3A H3A2 103.7 . . ?
H3A1 C3A H3A2 105.3 . . ?
C3A C4A H4AA 109.5 . . ?
C3A C4A H4AB 109.5 . . ?
H4AA C4A H4AB 109.5 . . ?
C3A C4A H4AC 109.5 . . ?
H4AA C4A H4AC 109.5 . . ?
H4AB C4A H4AC 109.5 . . ?
C3A O1A C1A 155(3) . . ?
N2 C1 N1 127.0(2) . . ?
N2 C1 O1 120.3(2) . . ?
N1 C1 O1 112.7(2) . . ?
C3 C2 C7 120.5(2) . . ?
C3 C2 O1 117.6(2) . . ?
C7 C2 O1 121.6(2) . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 Br1 119.7(2) . . ?
C4 C3 Br1 120.1(2) . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 117.9(2) . . ?
C4 C5 C8 122.6(2) . . ?
C6 C5 C8 119.5(2) . . ?
C7 C6 C5 121.8(3) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C2 C7 C6 119.0(2) . . ?
C2 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C5 C8 C9 112.9(2) . . ?
C5 C8 C13 110.0(2) . . ?
C9 C8 C13 108.2(2) . . ?
C5 C8 C14 109.0(2) . . ?
C9 C8 C14 108.1(2) . . ?
C13 C8 C14 108.6(2) . . ?
C8 C9 C10 110.6(2) . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C15 C10 C11 109.7(3) . . ?
C15 C10 C9 110.2(2) . . ?
C11 C10 C9 109.0(2) . . ?
C15 C10 H10 109.3 . . ?
C11 C10 H10 109.3 . . ?
C9 C10 H10 109.3 . . ?
C10 C11 C12 110.9(2) . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.0 . . ?
C22 C12 C11 112.0(2) 3_666 . ?
C22 C12 C16 111.8(2) 3_666 . ?
C11 C12 C16 107.7(2) . . ?
C22 C12 C13 108.6(2) 3_666 . ?
C11 C12 C13 108.3(2) . . ?
C16 C12 C13 108.3(2) . . ?
C8 C13 C12 111.3(2) . . ?
C8 C13 H13A 109.4 . . ?
C12 C13 H13A 109.4 . . ?
C8 C13 H13B 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C17 C14 C8 110.9(2) . . ?
C17 C14 H14A 109.5 . . ?
C8 C14 H14A 109.5 . . ?
C17 C14 H14B 109.5 . . ?
C8 C14 H14B 109.5 . . ?
H14A C14 H14B 108.0 . . ?
C17 C15 C10 108.8(2) . . ?
C17 C15 H15A 109.9 . . ?
C10 C15 H15A 109.9 . . ?
C17 C15 H15B 109.9 . . ?
C10 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
C17 C16 C12 111.1(2) . . ?
C17 C16 H16A 109.4 . . ?
C12 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C12 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C15 C17 C16 110.7(2) . . ?
C15 C17 C14 109.8(3) . . ?
C16 C17 C14 108.0(2) . . ?
C15 C17 H17 109.4 . . ?
C16 C17 H17 109.4 . . ?
C14 C17 H17 109.4 . . ?
N3 C18 N4 126.8(3) . . ?
N3 C18 O2 120.0(2) . . ?
N4 C18 O2 113.2(2) . . ?
C24 C19 C20 120.6(3) . . ?
C24 C19 O2 118.3(3) . . ?
C20 C19 O2 121.0(3) . . ?
C19 C20 C21 119.8(3) . . ?
C19 C20 Br2 119.8(2) . . ?
C21 C20 Br2 120.4(2) . . ?
C22 C21 C20 121.0(3) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C21 C22 C23 117.8(3) . . ?
C21 C22 C12 121.0(2) . 3_666 ?
C23 C22 C12 121.1(3) . 3_666 ?
C24 C23 C22 121.6(3) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C19 C24 C23 119.2(3) . . ?
C19 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
N4 N1 C1 116.2(2) . . ?
C1 N2 N3 116.4(2) . . ?
C18 N3 N2 116.5(2) . . ?
N1 N4 C18 116.5(2) . . ?
C1 O1 C2 119.1(2) . . ?
C18 O2 C19 117.7(2) . . ?
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
C1A O1A 1.274(19) . ?
C1A C2A 1.503(10) . ?
C1A H1A1 0.9900 . ?
C1A H1A2 0.9900 . ?
C2A H2AA 0.9800 . ?
C2A H2AB 0.9800 . ?
C2A H2AC 0.9800 . ?
C3A O1A 1.05(2) . ?
C3A C4A 1.536(10) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C4A H4AA 0.9800 . ?
C4A H4AB 0.9800 . ?
C4A H4AC 0.9800 . ?
C1 N2 1.325(3) . ?
C1 N1 1.340(3) . ?
C1 O1 1.340(3) . ?
C2 C3 1.378(4) . ?
C2 C7 1.382(4) . ?
C2 O1 1.406(3) . ?
C3 C4 1.393(4) . ?
C3 Br1 1.885(3) . ?
C4 C5 1.391(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.399(4) . ?
C5 C8 1.529(3) . ?
C6 C7 1.383(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.536(4) . ?
C8 C13 1.545(3) . ?
C8 C14 1.548(4) . ?
C9 C10 1.539(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.529(5) . ?
C10 C11 1.532(4) . ?
C10 H10 1.0000 . ?
C11 C12 1.542(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C22 1.528(4) 3_666 ?
C12 C16 1.542(4) . ?
C12 C13 1.551(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C17 1.537(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C17 1.520(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.533(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17 1.0000 . ?
C18 N3 1.329(3) . ?
C18 N4 1.335(4) . ?
C18 O2 1.343(3) . ?
C19 C24 1.372(5) . ?
C19 C20 1.378(5) . ?
C19 O2 1.405(3) . ?
C20 C21 1.387(4) . ?
C20 Br2 1.878(3) . ?
C21 C22 1.383(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.394(4) . ?
C23 C24 1.384(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
N1 N4 1.324(3) . ?
N2 N3 1.330(3) . ?
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
C4A C3A O1A C1A 131(5) . . . . ?
C2A C1A O1A C3A -126(6) . . . . ?
C7 C2 C3 C4 0.5(4) . . . . ?
O1 C2 C3 C4 -174.4(2) . . . . ?
C7 C2 C3 Br1 -179.2(2) . . . . ?
O1 C2 C3 Br1 6.0(3) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
Br1 C3 C4 C5 179.1(2) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C3 C4 C5 C8 177.6(2) . . . . ?
C4 C5 C6 C7 2.2(4) . . . . ?
C8 C5 C6 C7 -176.2(2) . . . . ?
C3 C2 C7 C6 0.9(4) . . . . ?
O1 C2 C7 C6 175.5(2) . . . . ?
C5 C6 C7 C2 -2.3(4) . . . . ?
C4 C5 C8 C9 2.6(4) . . . . ?
C6 C5 C8 C9 -179.1(2) . . . . ?
C4 C5 C8 C13 123.5(3) . . . . ?
C6 C5 C8 C13 -58.2(3) . . . . ?
C4 C5 C8 C14 -117.6(3) . . . . ?
C6 C5 C8 C14 60.8(3) . . . . ?
C5 C8 C9 C10 -178.3(2) . . . . ?
C13 C8 C9 C10 59.8(3) . . . . ?
C14 C8 C9 C10 -57.6(3) . . . . ?
C8 C9 C10 C15 60.0(3) . . . . ?
C8 C9 C10 C11 -60.4(3) . . . . ?
C15 C10 C11 C12 -61.0(3) . . . . ?
C9 C10 C11 C12 59.8(3) . . . . ?
C10 C11 C12 C22 -178.3(2) . . . 3_666 ?
C10 C11 C12 C16 58.4(3) . . . . ?
C10 C11 C12 C13 -58.5(3) . . . . ?
C5 C8 C13 C12 176.9(2) . . . . ?
C9 C8 C13 C12 -59.3(3) . . . . ?
C14 C8 C13 C12 57.8(3) . . . . ?
C22 C12 C13 C8 -179.6(2) 3_666 . . . ?
C11 C12 C13 C8 58.6(3) . . . . ?
C16 C12 C13 C8 -58.0(3) . . . . ?
C5 C8 C14 C17 -179.0(2) . . . . ?
C9 C8 C14 C17 57.9(3) . . . . ?
C13 C8 C14 C17 -59.2(3) . . . . ?
C11 C10 C15 C17 59.9(3) . . . . ?
C9 C10 C15 C17 -60.2(3) . . . . ?
C22 C12 C16 C17 179.4(2) 3_666 . . . ?
C11 C12 C16 C17 -57.2(3) . . . . ?
C13 C12 C16 C17 59.8(3) . . . . ?
C10 C15 C17 C16 -59.1(3) . . . . ?
C10 C15 C17 C14 60.1(3) . . . . ?
C12 C16 C17 C15 59.0(3) . . . . ?
C12 C16 C17 C14 -61.2(3) . . . . ?
C8 C14 C17 C15 -60.1(3) . . . . ?
C8 C14 C17 C16 60.7(3) . . . . ?
C24 C19 C20 C21 -0.8(4) . . . . ?
O2 C19 C20 C21 174.4(3) . . . . ?
C24 C19 C20 Br2 179.4(2) . . . . ?
O2 C19 C20 Br2 -5.5(4) . . . . ?
C19 C20 C21 C22 0.1(4) . . . . ?
Br2 C20 C21 C22 179.9(2) . . . . ?
C20 C21 C22 C23 0.5(4) . . . . ?
C20 C21 C22 C12 177.4(3) . . . 3_666 ?
C21 C22 C23 C24 -0.4(4) . . . . ?
C12 C22 C23 C24 -177.3(2) 3_666 . . . ?
C20 C19 C24 C23 0.8(4) . . . . ?
O2 C19 C24 C23 -174.4(2) . . . . ?
C22 C23 C24 C19 -0.3(4) . . . . ?
N2 C1 N1 N4 -6.3(5) . . . . ?
O1 C1 N1 N4 176.5(3) . . . . ?
N1 C1 N2 N3 7.1(5) . . . . ?
O1 C1 N2 N3 -176.0(3) . . . . ?
N4 C18 N3 N2 -6.4(5) . . . . ?
O2 C18 N3 N2 176.1(3) . . . . ?
C1 N2 N3 C18 -0.7(4) . . . . ?
C1 N1 N4 C18 -0.7(4) . . . . ?
N3 C18 N4 N1 7.1(5) . . . . ?
O2 C18 N4 N1 -175.3(3) . . . . ?
N2 C1 O1 C2 3.3(4) . . . . ?
N1 C1 O1 C2 -179.3(2) . . . . ?
C3 C2 O1 C1 -124.6(3) . . . . ?
C7 C2 O1 C1 60.6(4) . . . . ?
N3 C18 O2 C19 1.6(4) . . . . ?
N4 C18 O2 C19 -176.3(3) . . . . ?
C24 C19 O2 C18 -105.8(3) . . . . ?
C20 C19 O2 C18 79.0(4) . . . . ?
