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#$Date: 2022-09-09 01:28:47 +0300 (Fri, 09 Sep 2022) $
#$Revision: 277735 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/54/7245462.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_7245462
loop_
_publ_author_name
'Tominaga, Masahide'
'Hyodo, Tadashi'
'Mizuno, Kosuke'
'Kawahata, Masatoshi'
'Yamaguchi, Kentaro'
_publ_section_title
;
 Water adsorption in porous organic crystals of adamantane-bearing
 macrocycles
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE01030E
_journal_year                    2022
_chemical_formula_moiety         'C48 H40 Br4 N8 O4'
_chemical_formula_sum            'C48 H40 Br4 N8 O4'
_chemical_formula_weight         1112.52
_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_date             2022-04-23
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-07-14 deposited with the CCDC.	2022-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.423(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.0547(9)
_cell_length_b                   7.0993(5)
_cell_length_c                   23.8784(15)
_cell_measurement_reflns_used    9742
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.44
_cell_measurement_theta_min      3.61
_cell_volume                     2647.2(3)
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.24
_diffrn_measured_fraction_theta_full 0.000
_diffrn_measured_fraction_theta_max 0.744
_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  0.1009
_diffrn_reflns_av_unetI/netI     0.1006
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.744
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            18549
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.744
_diffrn_reflns_theta_full        2.500
_diffrn_reflns_theta_max         80.762
_diffrn_reflns_theta_min         3.021
_diffrn_source                   'rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    4.090
_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    1.396
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.884
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.127
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1507
_refine_ls_R_factor_gt           0.1003
_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)+(0.1621P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2746
_refine_ls_wR_factor_ref         0.2992
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2294
_reflns_number_total             4328
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01030e2.cif
_cod_data_source_block           3b_MASK
_cod_database_code               7245462
_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_max   0.822
_shelx_estimated_absorpt_t_min   0.685
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C20(H20A,H20B), C22(H22A,H22B), C23(H23A,H23B),
 C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C15(H15), C17(H17), C18(H18)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 152 electrons were 
found in a volume of 692Å³ in 1 void per unit cell. 
This is consistent with the presence of 
8[H2O] per Formula Unit 
which account for 160 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
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
C1 C 0.7822(5) 0.7181(17) 0.6893(5) 0.062(3) Uani 1 1 d . . . . .
C2 C 0.8388(5) 0.7811(16) 0.6087(5) 0.050(3) Uani 1 1 d . . . . .
C3 C 0.8676(5) 0.6673(17) 0.5723(4) 0.056(3) Uani 1 1 d . . . . .
C4 C 0.8658(5) 0.7193(17) 0.5169(4) 0.057(3) Uani 1 1 d . . . . .
H4 H 0.884972 0.633581 0.492069 0.068 Uiso 1 1 calc R U . . .
C5 C 0.8367(5) 0.8938(16) 0.4968(4) 0.050(3) Uani 1 1 d . . . . .
C6 C 0.8070(5) 1.0136(16) 0.5346(4) 0.056(3) Uani 1 1 d . . . . .
H6 H 0.784856 1.134798 0.522462 0.068 Uiso 1 1 calc R U . . .
C7 C 0.8108(6) 0.9497(17) 0.5914(4) 0.055(3) Uani 1 1 d . . . . .
H7 H 0.792571 1.031414 0.617750 0.066 Uiso 1 1 calc R U . . .
C8 C 0.8366(5) 0.9677(15) 0.4382(4) 0.052(3) Uani 1 1 d . . . . .
C9 C 0.8758(6) 0.8199(17) 0.4025(4) 0.061(3) Uani 1 1 d . . . . .
H9A H 0.840510 0.704070 0.397037 0.073 Uiso 1 1 calc R U . . .
H9B H 0.934439 0.785878 0.423765 0.073 Uiso 1 1 calc R U . . .
C10 C 0.8787(6) 0.9056(18) 0.3420(4) 0.067(3) Uani 1 1 d . . . . .
H10 H 0.902349 0.809390 0.319273 0.080 Uiso 1 1 calc R U . . .
C11 C 0.8943(6) 1.1456(17) 0.4426(4) 0.068(3) Uani 1 1 d . . . . .
H11A H 0.872148 1.243168 0.464974 0.081 Uiso 1 1 calc R U . . .
H11B H 0.952918 1.112542 0.464069 0.081 Uiso 1 1 calc R U . . .
C12 C 0.6576(5) 0.7114(17) 0.7376(4) 0.059(3) Uani 1 1 d . . . . .
C13 C 0.5120(6) 0.758(2) 0.7390(4) 0.067(4) Uani 1 1 d . . . . .
C14 C 0.4626(9) 0.633(2) 0.7061(6) 0.091(4) Uani 1 1 d . . . . .
C15 C 0.3762(5) 0.6707(18) 0.6778(4) 0.059(3) Uani 1 1 d . . . . .
H15 H 0.342092 0.579616 0.653690 0.071 Uiso 1 1 calc R U . . .
C16 C 0.3434(5) 0.8486(17) 0.6871(4) 0.053(3) Uani 1 1 d . . . . .
C17 C 0.3956(5) 0.9693(16) 0.7218(4) 0.056(3) Uani 1 1 d . . . . .
H17 H 0.372378 1.087793 0.728793 0.067 Uiso 1 1 calc R U . . .
C18 C 0.4808(5) 0.9348(19) 0.7485(4) 0.063(3) Uani 1 1 d . . . . .
H18 H 0.515668 1.026563 0.771868 0.076 Uiso 1 1 calc R U . . .
C19 C 0.2517(5) 0.8995(17) 0.6557(4) 0.062(3) Uani 1 1 d . . . . .
C20 C 0.1928(5) 0.7189(19) 0.6470(4) 0.069(4) Uani 1 1 d . . . . .
H20A H 0.215735 0.624447 0.623964 0.083 Uiso 1 1 calc R U . . .
H20B H 0.192814 0.662416 0.684856 0.083 Uiso 1 1 calc R U . . .
C21 C 0.1011(6) 0.771(2) 0.6160(4) 0.079(4) Uani 1 1 d . . . . .
H21 H 0.064485 0.655909 0.610041 0.094 Uiso 1 1 calc R U . . .
C22 C 0.0636(5) 0.9166(18) 0.6504(4) 0.068(4) Uani 1 1 d . . . . .
H22A H 0.061638 0.864376 0.688524 0.081 Uiso 1 1 calc R U . . .
H22B H 0.004569 0.949611 0.629740 0.081 Uiso 1 1 calc R U . . .
C23 C 0.2124(5) 1.0481(18) 0.6891(4) 0.068(4) Uani 1 1 d . . . . .
H23A H 0.212928 0.999591 0.728032 0.081 Uiso 1 1 calc R U . . .
H23B H 0.247473 1.164127 0.693446 0.081 Uiso 1 1 calc R U . . .
C24 C 0.2502(5) 0.9796(14) 0.5956(4) 0.045(2) Uani 1 1 d . . . . .
H24A H 0.287465 1.092363 0.600023 0.054 Uiso 1 1 calc R U . . .
H24B H 0.274735 0.884656 0.573610 0.054 Uiso 1 1 calc R U . . .
Br1 Br 0.90624(7) 0.41944(19) 0.59706(5) 0.0677(5) Uani 1 1 d . . . . .
Br2 Br 0.50674(9) 0.3928(2) 0.69336(8) 0.1068(7) Uani 1 1 d . . . . .
N1 N 0.7973(5) 0.6574(14) 0.7444(4) 0.060(2) Uani 1 1 d . . . . .
N2 N 0.7019(4) 0.7594(16) 0.6565(3) 0.068(3) Uani 1 1 d . . . . .
N3 N 0.6384(4) 0.7616(17) 0.6843(4) 0.081(3) Uani 1 1 d . . . . .
N4 N 0.7335(4) 0.6565(16) 0.7692(3) 0.074(3) Uani 1 1 d . . . . .
O1 O 0.8471(3) 0.7237(11) 0.6659(3) 0.061(2) Uani 1 1 d . . . . .
O2 O 0.5953(3) 0.7120(13) 0.7688(3) 0.075(2) 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'
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
N1 C1 N2 123.6(8) . . ?
O1 C1 N1 116.8(8) . . ?
O1 C1 N2 119.4(9) . . ?
C3 C2 O1 119.1(10) . . ?
C7 C2 C3 119.3(11) . . ?
C7 C2 O1 121.3(10) . . ?
C2 C3 C4 122.0(11) . . ?
C2 C3 Br1 119.2(8) . . ?
C4 C3 Br1 118.7(9) . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.8(10) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 117.6(9) . . ?
C4 C5 C8 124.8(10) . . ?
C6 C5 C8 117.6(10) . . ?
C5 C6 H6 120.8 . . ?
C5 C6 C7 118.4(10) . . ?
C7 C6 H6 120.8 . . ?
C2 C7 C6 121.9(10) . . ?
C2 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C5 C8 C9 111.1(9) . . ?
C5 C8 C11 110.6(8) . . ?
C11 C8 C9 105.7(8) . . ?
C24 C8 C5 113.2(8) 3_676 . ?
C24 C8 C9 108.4(7) 3_676 . ?
C24 C8 C11 107.5(9) 3_676 . ?
C8 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
C8 C9 C10 109.9(9) . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
C9 C10 H10 109.2 . . ?
C22 C10 C9 110.5(8) 3_676 . ?
C22 C10 H10 109.2 3_676 . ?
C23 C10 C9 107.5(8) 3_676 . ?
C23 C10 H10 109.2 3_676 . ?
C23 C10 C22 111.3(10) 3_676 3_676 ?
C8 C11 H11A 108.8 . . ?
C8 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C21 C11 C8 113.9(8) 3_676 . ?
C21 C11 H11A 108.8 3_676 . ?
C21 C11 H11B 108.8 3_676 . ?
N3 C12 N4 128.1(8) . . ?
N3 C12 O2 119.8(8) . . ?
N4 C12 O2 112.1(8) . . ?
C14 C13 C18 120.9(11) . . ?
C14 C13 O2 121.3(15) . . ?
C18 C13 O2 117.6(11) . . ?
C13 C14 C15 123.0(13) . . ?
C13 C14 Br2 120.2(12) . . ?
C15 C14 Br2 116.8(11) . . ?
C14 C15 H15 121.5 . . ?
C16 C15 C14 116.9(10) . . ?
C16 C15 H15 121.5 . . ?
C15 C16 C19 119.2(9) . . ?
C17 C16 C15 117.9(8) . . ?
C17 C16 C19 122.9(10) . . ?
C16 C17 H17 117.4 . . ?
C16 C17 C18 125.3(11) . . ?
C18 C17 H17 117.4 . . ?
C13 C18 C17 115.9(11) . . ?
C13 C18 H18 122.1 . . ?
C17 C18 H18 122.1 . . ?
C16 C19 C20 110.5(9) . . ?
C16 C19 C23 111.7(8) . . ?
C16 C19 C24 110.3(8) . . ?
C23 C19 C20 108.7(8) . . ?
C24 C19 C20 107.4(7) . . ?
C24 C19 C23 108.1(9) . . ?
C19 C20 H20A 109.6 . . ?
C19 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?
C21 C20 C19 110.2(10) . . ?
C21 C20 H20A 109.6 . . ?
C21 C20 H20B 109.6 . . ?
C11 C21 H21 109.7 3_676 . ?
C20 C21 C11 106.8(8) . 3_676 ?
C20 C21 H21 109.7 . . ?
C22 C21 C11 109.9(11) . 3_676 ?
C22 C21 C20 111.0(8) . . ?
C22 C21 H21 109.7 . . ?
C10 C22 H22A 110.0 3_676 . ?
C10 C22 H22B 110.0 3_676 . ?
C21 C22 C10 108.2(8) . 3_676 ?
C21 C22 H22A 110.0 . . ?
C21 C22 H22B 110.0 . . ?
H22A C22 H22B 108.4 . . ?
C10 C23 C19 111.1(8) 3_676 . ?
C10 C23 H23A 109.4 3_676 . ?
C10 C23 H23B 109.4 3_676 . ?
C19 C23 H23A 109.4 . . ?
C19 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C8 C24 C19 114.1(7) 3_676 . ?
C8 C24 H24A 108.7 3_676 . ?
C8 C24 H24B 108.7 3_676 . ?
C19 C24 H24A 108.7 . . ?
C19 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
N4 N1 C1 117.7(8) . . ?
N3 N2 C1 116.2(8) . . ?
C12 N3 N2 116.8(7) . . ?
N1 N4 C12 117.0(8) . . ?
C1 O1 C2 121.8(7) . . ?
C12 O2 C13 116.9(7) . . ?
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
C1 N1 1.354(12) . ?
C1 N2 1.375(11) . ?
C1 O1 1.292(10) . ?
C2 C3 1.345(14) . ?
C2 C7 1.311(13) . ?
C2 O1 1.401(11) . ?
C3 C4 1.366(13) . ?
C3 Br1 1.913(12) . ?
C4 H4 0.9500 . ?
C4 C5 1.371(14) . ?
C5 C6 1.402(14) . ?
C5 C8 1.494(13) . ?
C6 H6 0.9500 . ?
C6 C7 1.419(13) . ?
C7 H7 0.9500 . ?
C8 C9 1.573(14) . ?
C8 C11 1.555(14) . ?
C8 C24 1.488(12) 3_676 ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.579(14) . ?
C10 H10 1.0000 . ?
C10 C22 1.551(15) 3_676 ?
C10 C23 1.514(12) 3_676 ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C21 1.535(14) 3_676 ?
C12 N3 1.288(11) . ?
C12 N4 1.335(11) . ?
C12 O2 1.379(10) . ?
C13 C14 1.317(17) . ?
C13 C18 1.391(17) . ?
C13 O2 1.401(12) . ?
C14 C15 1.420(17) . ?
C14 Br2 1.900(14) . ?
C15 H15 0.9500 . ?
C15 C16 1.405(15) . ?
C16 C17 1.343(13) . ?
C16 C19 1.533(12) . ?
C17 H17 0.9500 . ?
C17 C18 1.391(12) . ?
C18 H18 0.9500 . ?
C19 C20 1.577(15) . ?
C19 C23 1.543(15) . ?
C19 C24 1.539(14) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.532(13) . ?
C21 H21 1.0000 . ?
C21 C22 1.527(16) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
N1 N4 1.296(9) . ?
N2 N3 1.339(9) . ?
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
C1 N1 N4 C12 1.6(16) . . . . ?
C1 N2 N3 C12 -5.0(18) . . . . ?
C2 C3 C4 C5 2.0(13) . . . . ?
C3 C2 C7 C6 2.3(14) . . . . ?
C3 C2 O1 C1 -126.0(11) . . . . ?
C3 C4 C5 C6 -1.6(13) . . . . ?
C3 C4 C5 C8 176.5(8) . . . . ?
C4 C5 C6 C7 1.6(12) . . . . ?
C4 C5 C8 C9 -0.8(11) . . . . ?
C4 C5 C8 C11 -118.0(11) . . . . ?
C4 C5 C8 C24 121.4(10) . . . 3_676 ?
C5 C6 C7 C2 -2.0(13) . . . . ?
C5 C8 C9 C10 -177.5(7) . . . . ?
C5 C8 C11 C21 179.1(10) . . . 3_676 ?
C6 C5 C8 C9 177.3(7) . . . . ?
C6 C5 C8 C11 60.1(11) . . . . ?
C6 C5 C8 C24 -60.5(11) . . . 3_676 ?
C7 C2 C3 C4 -2.3(13) . . . . ?
C7 C2 C3 Br1 -178.8(7) . . . . ?
C7 C2 O1 C1 60.2(13) . . . . ?
C8 C5 C6 C7 -176.7(7) . . . . ?
C8 C9 C10 C22 61.4(9) . . . 3_676 ?
C8 C9 C10 C23 -60.3(11) . . . 3_676 ?
C9 C8 C11 C21 58.7(12) . . . 3_676 ?
C11 C8 C9 C10 -57.4(9) . . . . ?
C11 C21 C22 C10 -58.6(9) 3_676 . . 3_676 ?
C13 C14 C15 C16 -1.3(17) . . . . ?
C14 C13 C18 C17 0.4(16) . . . . ?
C14 C13 O2 C12 78.9(14) . . . . ?
C14 C15 C16 C17 -0.2(15) . . . . ?
C14 C15 C16 C19 177.6(9) . . . . ?
C15 C16 C17 C18 1.8(16) . . . . ?
C15 C16 C19 C20 32.7(12) . . . . ?
C15 C16 C19 C23 153.9(10) . . . . ?
C15 C16 C19 C24 -85.9(11) . . . . ?
C16 C17 C18 C13 -2.0(16) . . . . ?
C16 C19 C20 C21 179.6(8) . . . . ?
C16 C19 C23 C10 -179.0(9) . . . 3_676 ?
C16 C19 C24 C8 179.7(9) . . . 3_676 ?
C17 C16 C19 C20 -149.6(9) . . . . ?
C17 C16 C19 C23 -28.5(14) . . . . ?
C17 C16 C19 C24 91.8(11) . . . . ?
C18 C13 C14 C15 1.1(18) . . . . ?
C18 C13 C14 Br2 179.7(8) . . . . ?
C18 C13 O2 C12 -105.8(12) . . . . ?
C19 C16 C17 C18 -175.8(10) . . . . ?
C19 C20 C21 C11 60.3(12) . . . 3_676 ?
C19 C20 C21 C22 -59.5(12) . . . . ?
C20 C19 C23 C10 -56.8(12) . . . 3_676 ?
C20 C19 C24 C8 59.2(11) . . . 3_676 ?
C20 C21 C22 C10 59.4(12) . . . 3_676 ?
C23 C19 C20 C21 56.6(11) . . . . ?
C23 C19 C24 C8 -57.8(10) . . . 3_676 ?
C24 C8 C9 C10 57.6(10) 3_676 . . . ?
C24 C8 C11 C21 -57.0(12) 3_676 . . 3_676 ?
C24 C19 C20 C21 -60.0(10) . . . . ?
C24 C19 C23 C10 59.4(12) . . . 3_676 ?
Br1 C3 C4 C5 178.4(6) . . . . ?
Br2 C14 C15 C16 -179.9(7) . . . . ?
N1 C1 N2 N3 8.8(18) . . . . ?
N1 C1 O1 C2 178.9(10) . . . . ?
N2 C1 N1 N4 -7.1(18) . . . . ?
N2 C1 O1 C2 3.6(17) . . . . ?
N3 C12 N4 N1 2(2) . . . . ?
N3 C12 O2 C13 3.7(17) . . . . ?
N4 C12 N3 N2 0(2) . . . . ?
N4 C12 O2 C13 -176.7(11) . . . . ?
O1 C1 N1 N4 177.8(10) . . . . ?
O1 C1 N2 N3 -176.2(11) . . . . ?
O1 C2 C3 C4 -176.3(7) . . . . ?
O1 C2 C3 Br1 7.3(11) . . . . ?
O1 C2 C7 C6 176.1(8) . . . . ?
O2 C12 N3 N2 179.5(10) . . . . ?
O2 C12 N4 N1 -177.6(10) . . . . ?
O2 C13 C14 C15 176.3(10) . . . . ?
O2 C13 C14 Br2 -5.2(15) . . . . ?
O2 C13 C18 C17 -174.9(8) . . . . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.469 0.000 346.2 76.1 '8 H2O'
2 0.500 -0.244 0.500 346.2 76.1 '8 H2O'
