#------------------------------------------------------------------------------
#$Date: 2021-03-05 03:48:56 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262588 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/22/7242213.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_7242213
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            'C56 H50 Br4 N8 O4'
_chemical_formula_weight         1218.68
_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   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                 91.184(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.6814(17)
_cell_length_b                   14.159(3)
_cell_length_c                   22.547(5)
_cell_measurement_reflns_used    9742
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.44
_cell_measurement_theta_min      3.61
_cell_volume                     2451.7(9)
_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 0.998
_diffrn_measured_fraction_theta_max 0.970
_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  0.0373
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            35606
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.994
_diffrn_reflns_theta_min         3.922
_diffrn_source                   'rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    4.476
_exptl_absorpt_correction_T_max  0.7643
_exptl_absorpt_correction_T_min  0.6619
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1228
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.691
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.068
_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     373
_refine_ls_number_reflns         5198
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0297
_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)+(0.0499P)²+2.1550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0859
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4945
_reflns_number_total             5198
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01782e2.cif
_cod_data_source_block           1e
_cod_depositor_comments
'Adding full bibliography for 7242212--7242215.cif.'
_cod_original_cell_volume        2451.6(9)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7242213
_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   0.663
_shelx_estimated_absorpt_t_max   0.716
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
C1A C 0.7199(15) 0.5729(11) 0.4855(5) 0.112(4) Uani 0.500(0) 1 d D . P A -1
C2A C 0.875(2) 0.6140(13) 0.4880(5) 0.214(15) Uani 0.500(0) 1 d D . P A -1
H2A H 0.876747 0.680929 0.484918 0.256 Uiso 0.500(0) 1 calc R U P A -1
C3A C 1.029(2) 0.5710(8) 0.4945(6) 0.25(2) Uani 0.500(0) 1 d D . P A -1
H3A H 1.136371 0.604577 0.495407 0.303 Uiso 0.500(0) 1 calc R U P A -1
C4A C 1.021(3) 0.4770(7) 0.4994(7) 0.105(4) Uani 0.500(0) 1 d D . P A -1
H4A H 1.128950 0.444446 0.501744 0.126 Uiso 0.500(0) 1 calc R U P A -1
C5A C 0.880(2) 0.4245(6) 0.5015(5) 0.090(4) Uani 0.500(0) 1 d . . P A -1
H5A H 0.882415 0.358027 0.507251 0.108 Uiso 0.500(0) 1 calc R U P A -1
C6A C 0.7219(15) 0.4781(10) 0.4943(4) 0.108(4) Uani 0.500(0) 1 d D . P A -1
H6A H 0.613911 0.445594 0.495612 0.130 Uiso 0.500(0) 1 calc R U P A -1
C7A C 0.5332(15) 0.5909(12) 0.4554(8) 0.204(10) Uani 0.500(0) 1 d D . P A -1
H7AA H 0.510204 0.658661 0.447583 0.244 Uiso 0.500(0) 1 calc R U P A -1
H7AB H 0.514363 0.553679 0.418652 0.244 Uiso 0.500(0) 1 calc R U P A -1
C8A C 0.4402(16) 0.5563(15) 0.5026(7) 0.175(8) Uani 0.500(0) 1 d D . P A -1
H8AA H 0.322563 0.583179 0.501512 0.263 Uiso 0.500(0) 1 calc R U P A -1
H8AB H 0.499242 0.573998 0.539946 0.263 Uiso 0.500(0) 1 calc R U P A -1
H8AC H 0.432920 0.487379 0.499869 0.263 Uiso 0.500(0) 1 calc R U P A -1
C1 C 0.3400(3) 0.88774(14) 0.39114(9) 0.0261(4) Uani 1 1 d . . . . .
C2 C 0.5408(3) 0.81158(13) 0.32997(9) 0.0244(4) Uani 1 1 d . . . . .
C3 C 0.6838(3) 0.79438(14) 0.36684(9) 0.0252(4) Uani 1 1 d . . . . .
C4 C 0.8002(3) 0.72290(14) 0.35361(9) 0.0264(4) Uani 1 1 d . . . . .
H4 H 0.895647 0.710464 0.379941 0.032 Uiso 1 1 calc R U . . .
C5 C 0.7791(3) 0.66892(13) 0.30205(9) 0.0247(4) Uani 1 1 d . . . . .
C6 C 0.6355(3) 0.68892(14) 0.26494(9) 0.0279(4) Uani 1 1 d . . . . .
H6 H 0.618701 0.653750 0.229396 0.034 Uiso 1 1 calc R U . . .
C7 C 0.5169(3) 0.75935(15) 0.27908(10) 0.0294(4) Uani 1 1 d . . . . .
H7 H 0.419494 0.771300 0.253539 0.035 Uiso 1 1 calc R U . . .
C8 C 0.9107(3) 0.59161(13) 0.28798(9) 0.0267(4) Uani 1 1 d . . . . .
C9 C 1.0985(3) 0.62730(15) 0.29950(13) 0.0375(5) Uani 1 1 d . . . . .
H9A H 1.121372 0.682625 0.273959 0.045 Uiso 1 1 calc R U . . .
H9AB H 1.112638 0.647240 0.341406 0.045 Uiso 1 1 calc R U . . .
C10 C 1.2283(3) 0.54857(16) 0.28609(13) 0.0409(6) Uani 1 1 d . . . . .
H10 H 1.349331 0.572411 0.293572 0.049 Uiso 1 1 calc R U . . .
C11 C 1.2085(4) 0.51879(18) 0.22091(13) 0.0500(7) Uani 1 1 d . . . . .
H11A H 1.229930 0.573631 0.194820 0.060 Uiso 1 1 calc R U . . .
H11B H 1.294802 0.469183 0.211846 0.060 Uiso 1 1 calc R U . . .
C12 C 1.0253(4) 0.48130(16) 0.20966(10) 0.0401(6) Uani 1 1 d . . . . .
H12 H 1.012449 0.461661 0.167187 0.048 Uiso 1 1 calc R U . . .
C13 C 0.8915(3) 0.55870(16) 0.22274(10) 0.0361(5) Uani 1 1 d . . . . .
H13A H 0.772427 0.534007 0.215385 0.043 Uiso 1 1 calc R U . . .
H13B H 0.909356 0.613029 0.195902 0.043 Uiso 1 1 calc R U . . .
C14 C 0.8799(3) 0.50504(13) 0.32819(9) 0.0229(4) Uani 1 1 d . . . . .
H14A H 0.759785 0.481514 0.321459 0.027 Uiso 1 1 calc R U . . .
H14B H 0.891950 0.524389 0.370272 0.027 Uiso 1 1 calc R U . . .
C15 C 1.1959(3) 0.46334(15) 0.32625(11) 0.0324(5) Uani 1 1 d . . . . .
H15A H 1.210938 0.482352 0.368293 0.039 Uiso 1 1 calc R U . . .
H15B H 1.281972 0.413278 0.317932 0.039 Uiso 1 1 calc R U . . .
C16 C 0.9913(3) 0.39602(15) 0.24962(10) 0.0314(4) Uani 1 1 d . . . . .
H16A H 1.075124 0.345090 0.240718 0.038 Uiso 1 1 calc R U . . .
H16B H 0.872314 0.371662 0.241637 0.038 Uiso 1 1 calc R U . . .
C17 C 0.1908(3) 0.89395(14) 0.48901(9) 0.0253(4) Uani 1 1 d . . . . .
C18 C 0.0928(3) 0.82055(14) 0.57540(9) 0.0264(4) Uani 1 1 d . . . . .
C19 C 0.2270(3) 0.77441(15) 0.60501(9) 0.0270(4) Uani 1 1 d . . . . .
C20 C 0.1943(3) 0.69537(14) 0.63948(9) 0.0267(4) Uani 1 1 d . . . . .
H20 H 0.288389 0.663777 0.659001 0.032 Uiso 1 1 calc R U . . .
C21 C 0.0249(3) 0.66179(14) 0.64579(9) 0.0241(4) Uani 1 1 d . . . . .
C22 C -0.1087(3) 0.71108(16) 0.61671(10) 0.0327(5) Uani 1 1 d . . . . .
H22 H -0.225408 0.690205 0.620592 0.039 Uiso 1 1 calc R U . . .
C23 C -0.0750(3) 0.79038(17) 0.58200(10) 0.0336(5) Uani 1 1 d . . . . .
H23 H -0.168369 0.823349 0.563014 0.040 Uiso 1 1 calc R U . . .
C24 C -0.0106(3) 0.57544(13) 0.68431(9) 0.0242(4) Uani 1 1 d . . . . .
Br1 Br 0.72857(3) 0.87238(2) 0.43401(2) 0.03306(9) Uani 1 1 d . . . . .
N1 N 0.3015(2) 0.97403(12) 0.41157(8) 0.0288(4) Uani 1 1 d . . . . .
N2 N 0.2910(2) 0.80565(13) 0.41326(8) 0.0303(4) Uani 1 1 d . . . . .
N3 N 0.2115(2) 0.80903(12) 0.46541(8) 0.0295(4) Uani 1 1 d . . . . .
N4 N 0.2250(2) 0.97740(12) 0.46316(8) 0.0277(4) Uani 1 1 d . . . . .
O1 O 0.42859(19) 0.88837(10) 0.34008(7) 0.0286(3) Uani 1 1 d . . . . .
O2 O 0.1222(2) 0.90310(10) 0.54292(7) 0.0292(3) Uani 1 1 d . . . . .
Br2A Br 0.4527(2) 0.82513(13) 0.60032(6) 0.0321(3) Uani 0.775(16) 1 d . . P B 1
Br2B Br 0.4684(10) 0.8056(12) 0.5917(7) 0.0582(18) Uani 0.225(16) 1 d . . P B 2
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'
Br Br -0.6763 1.2805 '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'
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
C2A C1A C6A 114.8(14) . . ?
C2A C1A C7A 138.3(15) . . ?
C6A C1A C7A 103.2(10) . . ?
C1A C2A C3A 126.7(18) . . ?
C1A C2A H2A 116.6 . . ?
C3A C2A H2A 116.6 . . ?
C2A C3A C4A 114.7(17) . . ?
C2A C3A H3A 122.6 . . ?
C4A C3A H3A 122.6 . . ?
C5A C4A C3A 127.4(19) . . ?
C5A C4A H4A 116.3 . . ?
C3A C4A H4A 116.3 . . ?
C4A C5A C6A 113.0(10) . . ?
C4A C5A H5A 123.5 . . ?
C6A C5A H5A 123.5 . . ?
C1A C6A C5A 123.1(12) . . ?
C1A C6A H6A 118.5 . . ?
C5A C6A H6A 118.5 . . ?
C8A C7A C1A 95.1(11) . . ?
C8A C7A H7AA 112.7 . . ?
C1A C7A H7AA 112.7 . . ?
C8A C7A H7AB 112.7 . . ?
C1A C7A H7AB 112.7 . . ?
H7AA C7A H7AB 110.2 . . ?
C7A C8A H8AA 109.5 . . ?
C7A C8A H8AB 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
C7A C8A H8AC 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
N2 C1 N1 127.22(19) . . ?
N2 C1 O1 118.69(18) . . ?
N1 C1 O1 113.93(17) . . ?
C7 C2 C3 119.78(18) . . ?
C7 C2 O1 118.62(18) . . ?
C3 C2 O1 121.25(18) . . ?
C2 C3 C4 120.40(19) . . ?
C2 C3 Br1 120.28(15) . . ?
C4 C3 Br1 119.25(16) . . ?
C3 C4 C5 120.88(19) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 117.61(18) . . ?
C4 C5 C8 119.88(19) . . ?
C6 C5 C8 122.51(18) . . ?
C7 C6 C5 121.28(19) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C2 C7 C6 120.0(2) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C5 C8 C9 110.51(16) . . ?
C5 C8 C14 109.64(16) . . ?
C9 C8 C14 108.33(18) . . ?
C5 C8 C13 111.25(18) . . ?
C9 C8 C13 109.20(19) . . ?
C14 C8 C13 107.83(16) . . ?
C10 C9 C8 109.78(18) . . ?
C10 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
C10 C9 H9AB 109.7 . . ?
C8 C9 H9AB 109.7 . . ?
H9A C9 H9AB 108.2 . . ?
C9 C10 C15 110.02(19) . . ?
C9 C10 C11 109.7(2) . . ?
C15 C10 C11 109.6(2) . . ?
C9 C10 H10 109.2 . . ?
C15 C10 H10 109.2 . . ?
C11 C10 H10 109.2 . . ?
C12 C11 C10 109.22(19) . . ?
C12 C11 H11A 109.8 . . ?
C10 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
C11 C12 C16 110.2(2) . . ?
C11 C12 C13 109.9(2) . . ?
C16 C12 C13 109.07(18) . . ?
C11 C12 H12 109.2 . . ?
C16 C12 H12 109.2 . . ?
C13 C12 H12 109.2 . . ?
C12 C13 C8 110.28(19) . . ?
C12 C13 H13A 109.6 . . ?
C8 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
C8 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C8 C14 C24 111.66(15) . 3_666 ?
C8 C14 H14A 109.3 . . ?
C24 C14 H14A 109.3 3_666 . ?
C8 C14 H14B 109.3 . . ?
C24 C14 H14B 109.3 3_666 . ?
H14A C14 H14B 107.9 . . ?
C10 C15 C24 110.53(19) . 3_666 ?
C10 C15 H15A 109.5 . . ?
C24 C15 H15A 109.5 3_666 . ?
C10 C15 H15B 109.5 . . ?
C24 C15 H15B 109.5 3_666 . ?
H15A C15 H15B 108.1 . . ?
C12 C16 C24 110.26(18) . 3_666 ?
C12 C16 H16A 109.6 . . ?
C24 C16 H16A 109.6 3_666 . ?
C12 C16 H16B 109.6 . . ?
C24 C16 H16B 109.6 3_666 . ?
H16A C16 H16B 108.1 . . ?
N3 C17 O2 120.25(18) . . ?
N3 C17 N4 126.62(19) . . ?
O2 C17 N4 113.06(17) . . ?
C23 C18 C19 119.67(19) . . ?
C23 C18 O2 118.65(18) . . ?
C19 C18 O2 121.42(19) . . ?
C18 C19 C20 120.68(19) . . ?
C18 C19 Br2A 118.14(16) . . ?
C20 C19 Br2A 121.10(17) . . ?
C18 C19 Br2B 121.7(3) . . ?
C20 C19 Br2B 117.1(3) . . ?
C19 C20 C21 120.76(19) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C22 C21 C20 117.42(19) . . ?
C22 C21 C24 122.02(18) . . ?
C20 C21 C24 120.55(18) . . ?
C21 C22 C23 121.6(2) . . ?
C21 C22 H22 119.2 . . ?
C23 C22 H22 119.2 . . ?
C18 C23 C22 119.8(2) . . ?
C18 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C21 C24 C15 111.89(17) . 3_666 ?
C21 C24 C16 108.89(16) . 3_666 ?
C15 C24 C16 108.16(17) 3_666 3_666 ?
C21 C24 C14 111.20(16) . 3_666 ?
C15 C24 C14 108.06(16) 3_666 3_666 ?
C16 C24 C14 108.54(16) 3_666 3_666 ?
N4 N1 C1 116.27(17) . . ?
C1 N2 N3 116.04(17) . . ?
C17 N3 N2 116.49(17) . . ?
N1 N4 C17 116.50(17) . . ?
C1 O1 C2 116.99(15) . . ?
C17 O2 C18 117.64(16) . . ?
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 C2A 1.326(10) . ?
C1A C6A 1.357(18) . ?
C1A C7A 1.595(9) . ?
C2A C3A 1.338(10) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.338(9) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.31(3) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.439(17) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A C8A 1.384(18) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
C1 N2 1.322(3) . ?
C1 N1 1.341(3) . ?
C1 O1 1.350(3) . ?
C2 C7 1.374(3) . ?
C2 C3 1.386(3) . ?
C2 O1 1.409(2) . ?
C3 C4 1.387(3) . ?
C3 Br1 1.900(2) . ?
C4 C5 1.398(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.399(3) . ?
C5 C8 1.528(3) . ?
C6 C7 1.392(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.545(3) . ?
C8 C14 1.546(3) . ?
C8 C13 1.547(3) . ?
C9 C10 1.530(3) . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 C15 1.532(3) . ?
C10 C11 1.533(4) . ?
C10 H10 1.0000 . ?
C11 C12 1.521(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C16 1.532(3) . ?
C12 C13 1.535(3) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C24 1.548(3) 3_666 ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C24 1.539(3) 3_666 ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C24 1.548(3) 3_666 ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 N3 1.326(3) . ?
C17 O2 1.341(2) . ?
C17 N4 1.346(3) . ?
C18 C23 1.369(3) . ?
C18 C19 1.381(3) . ?
C18 O2 1.400(2) . ?
C19 C20 1.388(3) . ?
C19 Br2A 1.881(3) . ?
C19 Br2B 1.935(8) . ?
C20 C21 1.396(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.393(3) . ?
C21 C24 1.527(3) . ?
C22 C23 1.396(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
N1 N4 1.315(3) . ?
N2 N3 1.337(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
C6A C1A C2A C3A 4.4(14) . . . . ?
C7A C1A C2A C3A -149.5(18) . . . . ?
C1A C2A C3A C4A -0.8(17) . . . . ?
C2A C3A C4A C5A -4(2) . . . . ?
C3A C4A C5A C6A 3(2) . . . . ?
C2A C1A C6A C5A -4.2(14) . . . . ?
C7A C1A C6A C5A 158.3(11) . . . . ?
C4A C5A C6A C1A 0.6(15) . . . . ?
C2A C1A C7A C8A -143.7(17) . . . . ?
C6A C1A C7A C8A 60.5(15) . . . . ?
C7 C2 C3 C4 -1.9(3) . . . . ?
O1 C2 C3 C4 -175.02(18) . . . . ?
C7 C2 C3 Br1 175.05(15) . . . . ?
O1 C2 C3 Br1 2.0(3) . . . . ?
C2 C3 C4 C5 2.1(3) . . . . ?
Br1 C3 C4 C5 -174.94(15) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C3 C4 C5 C8 179.03(18) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C8 C5 C6 C7 179.55(18) . . . . ?
C3 C2 C7 C6 0.5(3) . . . . ?
O1 C2 C7 C6 173.77(18) . . . . ?
C5 C6 C7 C2 0.8(3) . . . . ?
C4 C5 C8 C9 -43.9(3) . . . . ?
C6 C5 C8 C9 135.9(2) . . . . ?
C4 C5 C8 C14 75.5(2) . . . . ?
C6 C5 C8 C14 -104.8(2) . . . . ?
C4 C5 C8 C13 -165.37(18) . . . . ?
C6 C5 C8 C13 14.4(3) . . . . ?
C5 C8 C9 C10 179.14(19) . . . . ?
C14 C8 C9 C10 59.0(2) . . . . ?
C13 C8 C9 C10 -58.2(2) . . . . ?
C8 C9 C10 C15 -60.4(3) . . . . ?
C8 C9 C10 C11 60.3(2) . . . . ?
C9 C10 C11 C12 -61.2(2) . . . . ?
C15 C10 C11 C12 59.8(2) . . . . ?
C10 C11 C12 C16 -59.8(2) . . . . ?
C10 C11 C12 C13 60.4(2) . . . . ?
C11 C12 C13 C8 -59.2(2) . . . . ?
C16 C12 C13 C8 61.7(3) . . . . ?
C5 C8 C13 C12 179.87(18) . . . . ?
C9 C8 C13 C12 57.6(2) . . . . ?
C14 C8 C13 C12 -59.9(2) . . . . ?
C5 C8 C14 C24 -179.92(16) . . . 3_666 ?
C9 C8 C14 C24 -59.2(2) . . . 3_666 ?
C13 C8 C14 C24 58.8(2) . . . 3_666 ?
C9 C10 C15 C24 60.5(3) . . . 3_666 ?
C11 C10 C15 C24 -60.3(2) . . . 3_666 ?
C11 C12 C16 C24 59.9(2) . . . 3_666 ?
C13 C12 C16 C24 -60.7(3) . . . 3_666 ?
C23 C18 C19 C20 2.7(3) . . . . ?
O2 C18 C19 C20 176.69(18) . . . . ?
C23 C18 C19 Br2A -174.38(18) . . . . ?
O2 C18 C19 Br2A -0.4(3) . . . . ?
C23 C18 C19 Br2B 173.9(8) . . . . ?
O2 C18 C19 Br2B -12.0(8) . . . . ?
C18 C19 C20 C21 -1.1(3) . . . . ?
Br2A C19 C20 C21 175.84(16) . . . . ?
Br2B C19 C20 C21 -172.8(7) . . . . ?
C19 C20 C21 C22 -0.6(3) . . . . ?
C19 C20 C21 C24 -179.33(19) . . . . ?
C20 C21 C22 C23 0.7(3) . . . . ?
C24 C21 C22 C23 179.5(2) . . . . ?
C19 C18 C23 C22 -2.5(3) . . . . ?
O2 C18 C23 C22 -176.7(2) . . . . ?
C21 C22 C23 C18 0.8(4) . . . . ?
C22 C21 C24 C15 14.7(3) . . . 3_666 ?
C20 C21 C24 C15 -166.62(19) . . . 3_666 ?
C22 C21 C24 C16 -104.8(2) . . . 3_666 ?
C20 C21 C24 C16 73.9(2) . . . 3_666 ?
C22 C21 C24 C14 135.6(2) . . . 3_666 ?
C20 C21 C24 C14 -45.7(3) . . . 3_666 ?
N2 C1 N1 N4 9.0(3) . . . . ?
O1 C1 N1 N4 -175.80(17) . . . . ?
N1 C1 N2 N3 -8.3(3) . . . . ?
O1 C1 N2 N3 176.72(18) . . . . ?
O2 C17 N3 N2 -175.85(18) . . . . ?
N4 C17 N3 N2 7.4(3) . . . . ?
C1 N2 N3 C17 0.0(3) . . . . ?
C1 N1 N4 C17 -1.3(3) . . . . ?
N3 C17 N4 N1 -6.7(3) . . . . ?
O2 C17 N4 N1 176.35(17) . . . . ?
N2 C1 O1 C2 -33.0(3) . . . . ?
N1 C1 O1 C2 151.32(18) . . . . ?
C7 C2 O1 C1 123.4(2) . . . . ?
C3 C2 O1 C1 -63.4(3) . . . . ?
N3 C17 O2 C18 7.2(3) . . . . ?
N4 C17 O2 C18 -175.70(18) . . . . ?
C23 C18 O2 C17 -107.6(2) . . . . ?
C19 C18 O2 C17 78.3(3) . . . . ?
