#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/51/4025195.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_4025195
loop_
_publ_author_name
'Li-Xia Wang'
'De-Xian Wang'
'Zhi-Tang Huang'
'Mei-Xiang Wang'
_publ_section_title
;
 Synthesis and Highly Selective Bromination of Azacalix[4]pyrimidine
 Macrocycles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              741
_journal_page_last               747
_journal_paper_doi               10.1021/jo902245q
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C20 H17 Br3 N12'
_chemical_formula_sum            'C20 H17 Br3 N12'
_chemical_formula_weight         665.16
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                112.70(3)
_cell_angle_beta                 100.32(3)
_cell_angle_gamma                101.42(3)
_cell_formula_units_Z            4
_cell_length_a                   11.065(2)
_cell_length_b                   14.930(3)
_cell_length_c                   17.570(3)
_cell_measurement_reflns_used    473
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.17
_cell_volume                     2517.7(12)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0593
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            30964
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.65
_exptl_absorpt_coefficient_mu    4.842
_exptl_absorpt_correction_T_max  0.7938
_exptl_absorpt_correction_T_min  0.6980
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.755
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.531
_refine_diff_density_min         -0.784
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     642
_refine_ls_number_reflns         11480
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0532
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0486P)²+5.1156P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1306
_reflns_number_gt                9847
_reflns_number_total             11480
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902245q_si_003.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Numerical' changed to
'numerical' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        2517.7(9)
_cod_database_code               4025195
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.84850(4) 0.12442(3) -0.02018(3) 0.02756(11) Uani 1 1 d . . .
Br2 Br 0.89050(4) 0.35663(3) 0.24791(3) 0.02896(12) Uani 1 1 d . . .
Br3 Br 0.93835(4) 0.04258(3) 0.15949(3) 0.02848(12) Uani 1 1 d . . .
Br4 Br 0.23305(5) 0.49463(4) 0.24058(3) 0.03337(13) Uani 1 1 d . . .
Br5 Br 0.33960(5) 0.80788(4) 0.43206(4) 0.03116(17) Uani 0.8829(16) 1 d PD A 1
Br5' Br 0.5803(5) 0.7619(3) 0.3784(3) 0.0394(14) Uani 0.1171(16) 1 d PD A 2
Br6 Br 0.24950(5) 0.67176(4) 0.14712(3) 0.03362(13) Uani 1 1 d . . .
N1 N 1.2784(4) 0.1088(3) 0.0986(3) 0.0268(8) Uani 1 1 d . . .
N2 N 1.2202(3) 0.1691(3) -0.0059(2) 0.0245(8) Uani 1 1 d . . .
N3 N 1.0303(4) 0.4278(3) 0.0598(2) 0.0248(8) Uani 1 1 d . . .
N4 N 0.8209(3) 0.4146(3) 0.0797(2) 0.0249(8) Uani 1 1 d . . .
N5 N 0.5732(3) 0.1235(3) 0.0748(2) 0.0254(8) Uani 1 1 d . . .
N6 N 0.6382(3) 0.0825(3) 0.1912(3) 0.0267(8) Uani 1 1 d . . .
N7 N 1.0261(4) 0.2778(3) 0.3999(3) 0.0322(9) Uani 1 1 d . . .
N8 N 1.2216(4) 0.2792(3) 0.3605(3) 0.0338(9) Uani 1 1 d . . .
N9 N 1.1117(4) 0.2905(3) 0.0149(3) 0.0264(8) Uani 1 1 d . . .
N10 N 0.6863(3) 0.2632(3) 0.0640(2) 0.0229(8) Uani 1 1 d . . .
N11 N 0.8267(3) 0.1779(3) 0.3023(2) 0.0264(8) Uani 1 1 d . . .
N12 N 1.2301(4) 0.1665(3) 0.2279(3) 0.0294(9) Uani 1 1 d . . .
N13 N 0.5758(4) 0.6326(3) 0.1252(3) 0.0363(10) Uani 1 1 d . . .
N14 N 0.5623(4) 0.4992(4) 0.1690(3) 0.0391(10) Uani 1 1 d . . .
N15 N 0.5484(4) 0.5819(4) 0.4447(3) 0.0353(10) Uani 1 1 d . . .
N16 N 0.3770(4) 0.6220(3) 0.5041(3) 0.0321(9) Uani 1 1 d . . .
N17 N -0.0104(4) 0.5897(3) 0.3297(3) 0.0340(9) Uani 1 1 d . . .
N18 N -0.0223(4) 0.6976(3) 0.2580(3) 0.0361(10) Uani 1 1 d . . .
N19 N 0.3389(4) 0.9621(3) 0.3363(3) 0.0344(10) Uani 1 1 d . . .
N20 N 0.5356(4) 0.9396(3) 0.3061(3) 0.0318(9) Uani 1 1 d . . .
N21 N 0.5252(4) 0.5147(3) 0.2976(3) 0.0337(10) Uani 1 1 d . . .
N22 N 0.1776(4) 0.6035(3) 0.4208(3) 0.0273(8) Uani 1 1 d . . .
N23 N 0.1506(4) 0.8274(3) 0.2791(3) 0.0308(9) Uani 1 1 d . . .
N24 N 0.5525(4) 0.7883(3) 0.2092(3) 0.0300(9) Uani 1 1 d . . .
C1 C 1.2144(4) 0.1644(3) 0.1471(3) 0.0244(9) Uani 1 1 d . . .
C2 C 1.2757(4) 0.1146(4) 0.0254(3) 0.0269(10) Uani 1 1 d . . .
H2A H 1.3193 0.0747 -0.0096 0.032 Uiso 1 1 calc R . .
C3 C 1.1569(4) 0.2245(3) 0.0436(3) 0.0239(9) Uani 1 1 d . . .
C4 C 1.1469(4) 0.2219(3) 0.1198(3) 0.0236(9) Uani 1 1 d . . .
H4A H 1.0969 0.2571 0.1521 0.028 Uiso 1 1 calc R . .
C5 C 1.0127(4) 0.3286(3) 0.0383(3) 0.0214(9) Uani 1 1 d . . .
C6 C 0.9322(4) 0.4633(3) 0.0756(3) 0.0241(9) Uani 1 1 d . . .
H6A H 0.9428 0.5319 0.0852 0.029 Uiso 1 1 calc R . .
C7 C 0.8046(4) 0.3167(3) 0.0612(3) 0.0209(9) Uani 1 1 d . . .
C8 C 0.8948(4) 0.2679(3) 0.0343(3) 0.0223(9) Uani 1 1 d . . .
C9 C 0.6788(4) 0.2034(3) 0.1075(3) 0.0221(9) Uani 1 1 d . . .
C10 C 0.5577(4) 0.0698(4) 0.1196(3) 0.0270(10) Uani 1 1 d . . .
H10A H 0.4798 0.0161 0.0977 0.032 Uiso 1 1 calc R . .
C11 C 0.7453(4) 0.1611(3) 0.2240(3) 0.0235(9) Uani 1 1 d . . .
C12 C 0.7675(4) 0.2267(3) 0.1856(3) 0.0234(9) Uani 1 1 d . . .
C13 C 0.9591(4) 0.2091(4) 0.3197(3) 0.0258(9) Uani 1 1 d . . .
C14 C 1.1534(5) 0.3079(4) 0.4158(3) 0.0351(11) Uani 1 1 d . . .
H14A H 1.2008 0.3552 0.4731 0.042 Uiso 1 1 calc R . .
C15 C 1.1561(4) 0.2064(4) 0.2823(3) 0.0264(10) Uani 1 1 d . . .
C16 C 1.0238(4) 0.1649(3) 0.2594(3) 0.0239(9) Uani 1 1 d . . .
C17 C 1.1968(5) 0.3435(4) -0.0201(4) 0.0409(13) Uani 1 1 d . . .
H17A H 1.1453 0.3457 -0.0705 0.061 Uiso 1 1 calc R . .
H17B H 1.2594 0.3071 -0.0368 0.061 Uiso 1 1 calc R . .
H17C H 1.2422 0.4130 0.0239 0.061 Uiso 1 1 calc R . .
C18 C 0.5696(5) 0.2619(4) 0.0100(4) 0.0370(12) Uani 1 1 d . . .
H18A H 0.4947 0.2224 0.0177 0.056 Uiso 1 1 calc R . .
H18B H 0.5695 0.2308 -0.0504 0.056 Uiso 1 1 calc R . .
H18C H 0.5656 0.3316 0.0262 0.056 Uiso 1 1 calc R . .
C19 C 0.7680(5) 0.1713(4) 0.3691(3) 0.0396(13) Uani 1 1 d . . .
H19A H 0.8354 0.1845 0.4200 0.059 Uiso 1 1 calc R . .
H19B H 0.7084 0.1032 0.3474 0.059 Uiso 1 1 calc R . .
H19C H 0.7211 0.2219 0.3846 0.059 Uiso 1 1 calc R . .
C20 C 1.3414(5) 0.1407(5) 0.2639(4) 0.0449(14) Uani 1 1 d . . .
H20A H 1.3844 0.1139 0.2195 0.067 Uiso 1 1 calc R . .
H20B H 1.3123 0.0892 0.2835 0.067 Uiso 1 1 calc R . .
H20C H 1.4017 0.2017 0.3125 0.067 Uiso 1 1 calc R . .
C21 C 0.5465(4) 0.6884(4) 0.1962(3) 0.0273(10) Uani 1 1 d . A .
C22 C 0.5805(5) 0.5417(5) 0.1166(4) 0.0410(13) Uani 1 1 d . . .
H22A H 0.5995 0.5013 0.0660 0.049 Uiso 1 1 calc R . .
C23 C 0.5334(4) 0.5554(4) 0.2392(3) 0.0285(10) Uani 1 1 d . A .
C24 C 0.5234(5) 0.6528(4) 0.2552(3) 0.0294(10) Uani 1 1 d D . .
H24A H 0.5016 0.6925 0.3048 0.035 Uiso 0.8829(16) 1 calc PR A 1
C25 C 0.4729(5) 0.5541(4) 0.3660(3) 0.0312(11) Uani 1 1 d . . .
C26 C 0.4937(5) 0.6124(4) 0.5090(4) 0.0359(12) Uani 1 1 d . . .
H26A H 0.5454 0.6290 0.5647 0.043 Uiso 1 1 calc R . .
C27 C 0.3016(4) 0.5957(4) 0.4258(3) 0.0269(10) Uani 1 1 d . . .
C28 C 0.3462(4) 0.5564(3) 0.3527(3) 0.0262(10) Uani 1 1 d . . .
C29 C 0.1150(4) 0.6370(3) 0.3661(3) 0.0254(9) Uani 1 1 d . A .
C30 C -0.0718(5) 0.6245(4) 0.2788(4) 0.0398(13) Uani 1 1 d . . .
H30A H -0.1617 0.5927 0.2546 0.048 Uiso 1 1 calc R . .
C31 C 0.1037(4) 0.7473(4) 0.2965(3) 0.0298(10) Uani 1 1 d . A .
C32 C 0.1748(4) 0.7207(4) 0.3546(3) 0.0278(10) Uani 1 1 d D . .
H32A H 0.2618 0.7587 0.3854 0.033 Uiso 0.1171(16) 1 calc PR A 2
C33 C 0.2825(5) 0.8630(4) 0.2854(3) 0.0306(10) Uani 1 1 d . . .
C34 C 0.4618(5) 0.9946(4) 0.3425(3) 0.0356(11) Uani 1 1 d . . .
H34A H 0.5027 1.0652 0.3767 0.043 Uiso 1 1 calc R . .
C35 C 0.4774(4) 0.8411(4) 0.2522(3) 0.0276(10) Uani 1 1 d . . .
C36 C 0.3446(4) 0.8004(4) 0.2368(3) 0.0260(10) Uani 1 1 d . . .
C37 C 0.5810(9) 0.4326(6) 0.2923(5) 0.081(3) Uani 1 1 d . . .
H37A H 0.6133 0.4120 0.2416 0.122 Uiso 1 1 calc R . .
H37B H 0.5152 0.3745 0.2874 0.122 Uiso 1 1 calc R . .
H37C H 0.6520 0.4560 0.3442 0.122 Uiso 1 1 calc R . .
C38 C 0.1044(5) 0.5606(4) 0.4673(3) 0.0328(11) Uani 1 1 d . . .
H38A H 0.0193 0.5712 0.4591 0.049 Uiso 1 1 calc R . .
H38B H 0.1504 0.5943 0.5287 0.049 Uiso 1 1 calc R . .
H38C H 0.0946 0.4876 0.4449 0.049 Uiso 1 1 calc R . .
C39 C 0.0631(5) 0.8711(5) 0.2422(4) 0.0480(15) Uani 1 1 d . . .
H39A H -0.0248 0.8411 0.2410 0.072 Uiso 1 1 calc R . .
H39B H 0.0667 0.8568 0.1834 0.072 Uiso 1 1 calc R . .
H39C H 0.0886 0.9448 0.2772 0.072 Uiso 1 1 calc R . .
C40 C 0.6695(5) 0.8480(4) 0.2016(4) 0.0414(13) Uani 1 1 d . . .
H40A H 0.6631 0.9162 0.2124 0.062 Uiso 1 1 calc R . .
H40B H 0.6780 0.8141 0.1436 0.062 Uiso 1 1 calc R . .
H40C H 0.7450 0.8535 0.2439 0.062 Uiso 1 1 calc R . .
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'
Br Br -0.2901 2.4595 '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'
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
C2 N1 C1 115.3(4) . . ?
C2 N2 C3 115.3(4) . . ?
C6 N3 C5 116.9(4) . . ?
C6 N4 C7 115.4(4) . . ?
C10 N5 C9 117.0(4) . . ?
C10 N6 C11 116.0(4) . . ?
C14 N7 C13 116.6(4) . . ?
C14 N8 C15 116.1(4) . . ?
C5 N9 C3 123.2(4) . . ?
C5 N9 C17 117.7(4) . . ?
C3 N9 C17 116.7(4) . . ?
C9 N10 C7 122.5(3) . . ?
C9 N10 C18 119.5(4) . . ?
C7 N10 C18 117.5(4) . . ?
C13 N11 C11 121.5(4) . . ?
C13 N11 C19 120.2(4) . . ?
C11 N11 C19 118.0(4) . . ?
C1 N12 C15 123.0(4) . . ?
C1 N12 C20 118.6(4) . . ?
C15 N12 C20 117.8(4) . . ?
C22 N13 C21 115.0(4) . . ?
C22 N14 C23 115.5(5) . . ?
C25 N15 C26 115.6(4) . . ?
C26 N16 C27 116.9(4) . . ?
C29 N17 C30 115.8(4) . . ?
C30 N18 C31 116.1(4) . . ?
C34 N19 C33 115.0(4) . . ?
C34 N20 C35 117.1(4) . . ?
C23 N21 C25 122.4(4) . . ?
C23 N21 C37 119.5(4) . . ?
C25 N21 C37 117.9(4) . . ?
C29 N22 C27 123.3(4) . . ?
C29 N22 C38 118.8(4) . . ?
C27 N22 C38 117.3(4) . . ?
C31 N23 C33 122.3(4) . . ?
C31 N23 C39 120.6(4) . . ?
C33 N23 C39 116.6(4) . . ?
C35 N24 C21 122.7(4) . . ?
C35 N24 C40 117.5(4) . . ?
C21 N24 C40 116.9(4) . . ?
N1 C1 N12 114.5(4) . . ?
N1 C1 C4 122.0(4) . . ?
N12 C1 C4 123.3(4) . . ?
N1 C2 N2 128.5(4) . . ?
N1 C2 H2A 115.8 . . ?
N2 C2 H2A 115.8 . . ?
N2 C3 C4 122.3(4) . . ?
N2 C3 N9 114.7(4) . . ?
C4 C3 N9 122.8(4) . . ?
C3 C4 C1 116.4(4) . . ?
C3 C4 H4A 121.8 . . ?
C1 C4 H4A 121.8 . . ?
N3 C5 N9 116.3(4) . . ?
N3 C5 C8 119.9(4) . . ?
N9 C5 C8 123.6(4) . . ?
N3 C6 N4 127.8(4) . . ?
N3 C6 H6A 116.1 . . ?
N4 C6 H6A 116.1 . . ?
N4 C7 C8 122.0(4) . . ?
N4 C7 N10 116.3(4) . . ?
C8 C7 N10 121.6(4) . . ?
C7 C8 C5 117.4(4) . . ?
C7 C8 Br1 120.1(3) . . ?
C5 C8 Br1 122.0(3) . . ?
N5 C9 N10 115.7(4) . . ?
N5 C9 C12 119.9(4) . . ?
N10 C9 C12 124.2(4) . . ?
N6 C10 N5 127.6(4) . . ?
N6 C10 H10A 116.2 . . ?
N5 C10 H10A 116.2 . . ?
N6 C11 C12 121.2(4) . . ?
N6 C11 N11 115.9(4) . . ?
C12 C11 N11 122.6(4) . . ?
C11 C12 C9 118.0(4) . . ?
C11 C12 Br2 120.5(3) . . ?
C9 C12 Br2 120.1(3) . . ?
N7 C13 N11 117.1(4) . . ?
N7 C13 C16 120.1(4) . . ?
N11 C13 C16 122.5(4) . . ?
N8 C14 N7 127.3(5) . . ?
N8 C14 H14A 116.3 . . ?
N7 C14 H14A 116.3 . . ?
N8 C15 C16 121.8(4) . . ?
N8 C15 N12 115.9(4) . . ?
C16 C15 N12 121.9(4) . . ?
C15 C16 C13 117.3(4) . . ?
C15 C16 Br3 120.9(3) . . ?
C13 C16 Br3 121.1(3) . . ?
N9 C17 H17A 109.5 . . ?
N9 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N9 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N10 C18 H18A 109.5 . . ?
N10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N11 C19 H19A 109.5 . . ?
N11 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N11 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N12 C20 H20A 109.5 . . ?
N12 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N12 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N13 C21 C24 122.1(5) . . ?
N13 C21 N24 115.0(4) . . ?
C24 C21 N24 122.7(4) . . ?
N13 C22 N14 128.8(5) . . ?
N13 C22 H22A 115.6 . . ?
N14 C22 H22A 115.6 . . ?
N14 C23 N21 115.5(4) . . ?
N14 C23 C24 121.3(4) . . ?
N21 C23 C24 123.0(4) . . ?
C21 C24 C23 117.2(4) . . ?
C21 C24 Br5' 114.1(4) . . ?
C23 C24 Br5' 119.1(4) . . ?
C21 C24 H24A 121.4 . . ?
C23 C24 H24A 121.4 . . ?
Br5' C24 H24A 30.8 . . ?
N15 C25 C28 121.4(5) . . ?
N15 C25 N21 116.3(4) . . ?
C28 C25 N21 122.0(5) . . ?
N16 C26 N15 127.8(5) . . ?
N16 C26 H26A 116.1 . . ?
N15 C26 H26A 116.1 . . ?
N16 C27 N22 116.6(4) . . ?
N16 C27 C28 120.2(4) . . ?
N22 C27 C28 123.1(4) . . ?
C25 C28 C27 117.8(4) . . ?
C25 C28 Br4 120.5(4) . . ?
C27 C28 Br4 121.2(3) . . ?
N17 C29 N22 115.9(4) . . ?
N17 C29 C32 120.8(4) . . ?
N22 C29 C32 123.1(4) . . ?
N18 C30 N17 128.2(5) . . ?
N18 C30 H30A 115.9 . . ?
N17 C30 H30A 115.9 . . ?
N18 C31 N23 115.2(4) . . ?
N18 C31 C32 120.0(4) . . ?
N23 C31 C32 124.6(4) . . ?
C29 C32 C31 118.7(4) . . ?
C29 C32 Br5 118.7(4) . . ?
C31 C32 Br5 121.8(4) . . ?
C29 C32 H32A 120.7 . . ?
C31 C32 H32A 120.7 . . ?
Br5 C32 H32A 9.3 . . ?
N19 C33 C36 122.8(4) . . ?
N19 C33 N23 115.3(4) . . ?
C36 C33 N23 121.7(5) . . ?
N19 C34 N20 127.6(5) . . ?
N19 C34 H34A 116.2 . . ?
N20 C34 H34A 116.2 . . ?
N20 C35 N24 116.2(4) . . ?
N20 C35 C36 119.7(4) . . ?
N24 C35 C36 123.9(4) . . ?
C33 C36 C35 117.1(4) . . ?
C33 C36 Br6 120.2(4) . . ?
C35 C36 Br6 122.4(4) . . ?
N21 C37 H37A 109.5 . . ?
N21 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
N21 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N22 C38 H38A 109.5 . . ?
N22 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
N22 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N23 C39 H39A 109.5 . . ?
N23 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
N23 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
N24 C40 H40A 109.5 . . ?
N24 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
N24 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
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
Br1 C8 1.891(4) . ?
Br2 C12 1.896(4) . ?
Br3 C16 1.886(5) . ?
Br4 C28 1.886(5) . ?
Br5 C32 1.917(5) . ?
Br5' C24 2.030(6) . ?
Br6 C36 1.883(5) . ?
N1 C2 1.318(6) . ?
N1 C1 1.349(6) . ?
N2 C2 1.328(6) . ?
N2 C3 1.350(6) . ?
N3 C6 1.326(5) . ?
N3 C5 1.342(6) . ?
N4 C6 1.331(5) . ?
N4 C7 1.334(6) . ?
N5 C10 1.331(6) . ?
N5 C9 1.341(6) . ?
N6 C10 1.326(6) . ?
N6 C11 1.341(6) . ?
N7 C14 1.333(6) . ?
N7 C13 1.340(6) . ?
N8 C14 1.329(6) . ?
N8 C15 1.332(6) . ?
N9 C5 1.385(5) . ?
N9 C3 1.403(6) . ?
N9 C17 1.475(6) . ?
N10 C9 1.381(6) . ?
N10 C7 1.411(5) . ?
N10 C18 1.451(6) . ?
N11 C13 1.383(6) . ?
N11 C11 1.402(6) . ?
N11 C19 1.465(6) . ?
N12 C1 1.386(6) . ?
N12 C15 1.405(6) . ?
N12 C20 1.471(6) . ?
N13 C22 1.318(7) . ?
N13 C21 1.344(6) . ?
N14 C22 1.325(7) . ?
N14 C23 1.334(6) . ?
N15 C25 1.336(7) . ?
N15 C26 1.344(7) . ?
N16 C26 1.319(6) . ?
N16 C27 1.335(6) . ?
N17 C29 1.333(6) . ?
N17 C30 1.345(7) . ?
N18 C30 1.329(7) . ?
N18 C31 1.348(6) . ?
N19 C34 1.319(6) . ?
N19 C33 1.339(6) . ?
N20 C34 1.340(7) . ?
N20 C35 1.344(6) . ?
N21 C23 1.387(6) . ?
N21 C25 1.402(6) . ?
N21 C37 1.457(7) . ?
N22 C29 1.387(6) . ?
N22 C27 1.389(6) . ?
N22 C38 1.473(6) . ?
N23 C31 1.372(6) . ?
N23 C33 1.419(6) . ?
N23 C39 1.462(6) . ?
N24 C35 1.381(6) . ?
N24 C21 1.406(6) . ?
N24 C40 1.478(6) . ?
C1 C4 1.403(6) . ?
C2 H2A 0.9500 . ?
C3 C4 1.378(6) . ?
C4 H4A 0.9500 . ?
C5 C8 1.407(6) . ?
C6 H6A 0.9500 . ?
C7 C8 1.394(6) . ?
C9 C12 1.408(6) . ?
C10 H10A 0.9500 . ?
C11 C12 1.395(6) . ?
C13 C16 1.411(6) . ?
C14 H14A 0.9500 . ?
C15 C16 1.387(6) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C24 1.375(6) . ?
C22 H22A 0.9500 . ?
C23 C24 1.400(7) . ?
C24 H24A 0.9500 . ?
C25 C28 1.389(6) . ?
C26 H26A 0.9500 . ?
C27 C28 1.413(6) . ?
C29 C32 1.398(6) . ?
C30 H30A 0.9500 . ?
C31 C32 1.403(7) . ?
C32 H32A 0.9500 . ?
C33 C36 1.387(7) . ?
C34 H34A 0.9500 . ?
C35 C36 1.407(6) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
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
C2 N1 C1 N12 -173.1(4) . . . . ?
C2 N1 C1 C4 1.7(6) . . . . ?
C15 N12 C1 N1 -169.6(4) . . . . ?
C20 N12 C1 N1 20.0(6) . . . . ?
C15 N12 C1 C4 15.6(7) . . . . ?
C20 N12 C1 C4 -154.7(5) . . . . ?
C1 N1 C2 N2 1.2(7) . . . . ?
C3 N2 C2 N1 -0.9(7) . . . . ?
C2 N2 C3 C4 -2.2(6) . . . . ?
C2 N2 C3 N9 172.9(4) . . . . ?
C5 N9 C3 N2 158.7(4) . . . . ?
C17 N9 C3 N2 -39.3(6) . . . . ?
C5 N9 C3 C4 -26.2(7) . . . . ?
C17 N9 C3 C4 135.8(5) . . . . ?
N2 C3 C4 C1 4.8(6) . . . . ?
N9 C3 C4 C1 -170.0(4) . . . . ?
N1 C1 C4 C3 -4.5(6) . . . . ?
N12 C1 C4 C3 169.8(4) . . . . ?
C6 N3 C5 N9 174.7(4) . . . . ?
C6 N3 C5 C8 -0.6(6) . . . . ?
C3 N9 C5 N3 136.3(4) . . . . ?
C17 N9 C5 N3 -25.5(6) . . . . ?
C3 N9 C5 C8 -48.6(7) . . . . ?
C17 N9 C5 C8 149.6(5) . . . . ?
C5 N3 C6 N4 5.9(7) . . . . ?
C7 N4 C6 N3 -3.7(7) . . . . ?
C6 N4 C7 C8 -3.9(6) . . . . ?
C6 N4 C7 N10 -179.1(4) . . . . ?
C9 N10 C7 N4 -131.1(4) . . . . ?
C18 N10 C7 N4 56.8(6) . . . . ?
C9 N10 C7 C8 53.7(6) . . . . ?
C18 N10 C7 C8 -118.5(5) . . . . ?
N4 C7 C8 C5 8.5(6) . . . . ?
N10 C7 C8 C5 -176.5(4) . . . . ?
N4 C7 C8 Br1 -162.9(3) . . . . ?
N10 C7 C8 Br1 12.1(6) . . . . ?
N3 C5 C8 C7 -6.0(6) . . . . ?
N9 C5 C8 C7 179.0(4) . . . . ?
N3 C5 C8 Br1 165.1(3) . . . . ?
N9 C5 C8 Br1 -9.8(6) . . . . ?
C10 N5 C9 N10 -174.2(4) . . . . ?
C10 N5 C9 C12 0.3(6) . . . . ?
C7 N10 C9 N5 -149.7(4) . . . . ?
C18 N10 C9 N5 22.4(6) . . . . ?
C7 N10 C9 C12 36.1(6) . . . . ?
C18 N10 C9 C12 -151.8(4) . . . . ?
C11 N6 C10 N5 2.9(7) . . . . ?
C9 N5 C10 N6 -3.9(7) . . . . ?
C10 N6 C11 C12 1.7(6) . . . . ?
C10 N6 C11 N11 176.4(4) . . . . ?
C13 N11 C11 N6 142.4(4) . . . . ?
C19 N11 C11 N6 -43.6(6) . . . . ?
C13 N11 C11 C12 -43.0(6) . . . . ?
C19 N11 C11 C12 131.0(5) . . . . ?
N6 C11 C12 C9 -4.9(6) . . . . ?
N11 C11 C12 C9 -179.2(4) . . . . ?
N6 C11 C12 Br2 162.0(3) . . . . ?
N11 C11 C12 Br2 -12.4(6) . . . . ?
N5 C9 C12 C11 3.8(6) . . . . ?
N10 C9 C12 C11 177.7(4) . . . . ?
N5 C9 C12 Br2 -163.1(3) . . . . ?
N10 C9 C12 Br2 10.9(6) . . . . ?
C14 N7 C13 N11 -179.5(4) . . . . ?
C14 N7 C13 C16 6.2(7) . . . . ?
C11 N11 C13 N7 140.8(4) . . . . ?
C19 N11 C13 N7 -33.1(6) . . . . ?
C11 N11 C13 C16 -45.1(6) . . . . ?
C19 N11 C13 C16 141.0(5) . . . . ?
C15 N8 C14 N7 -5.7(8) . . . . ?
C13 N7 C14 N8 1.7(8) . . . . ?
C14 N8 C15 C16 1.6(7) . . . . ?
C14 N8 C15 N12 -171.6(4) . . . . ?
C1 N12 C15 N8 -124.6(5) . . . . ?
C20 N12 C15 N8 45.9(6) . . . . ?
C1 N12 C15 C16 62.1(6) . . . . ?
C20 N12 C15 C16 -127.4(5) . . . . ?
N8 C15 C16 C13 5.5(7) . . . . ?
N12 C15 C16 C13 178.4(4) . . . . ?
N8 C15 C16 Br3 -165.3(4) . . . . ?
N12 C15 C16 Br3 7.6(6) . . . . ?
N7 C13 C16 C15 -9.6(7) . . . . ?
N11 C13 C16 C15 176.4(4) . . . . ?
N7 C13 C16 Br3 161.2(4) . . . . ?
N11 C13 C16 Br3 -12.8(6) . . . . ?
C22 N13 C21 C24 0.1(7) . . . . ?
C22 N13 C21 N24 174.6(5) . . . . ?
C35 N24 C21 N13 151.2(4) . . . . ?
C40 N24 C21 N13 -48.6(6) . . . . ?
C35 N24 C21 C24 -34.3(7) . . . . ?
C40 N24 C21 C24 126.0(5) . . . . ?
C21 N13 C22 N14 -1.2(9) . . . . ?
C23 N14 C22 N13 1.1(9) . . . . ?
C22 N14 C23 N21 -174.7(5) . . . . ?
C22 N14 C23 C24 0.0(7) . . . . ?
C25 N21 C23 N14 -167.8(5) . . . . ?
C37 N21 C23 N14 16.8(8) . . . . ?
C25 N21 C23 C24 17.6(7) . . . . ?
C37 N21 C23 C24 -157.8(6) . . . . ?
N13 C21 C24 C23 0.9(7) . . . . ?
N24 C21 C24 C23 -173.3(4) . . . . ?
N13 C21 C24 Br5' 146.9(4) . . . . ?
N24 C21 C24 Br5' -27.2(6) . . . . ?
N14 C23 C24 C21 -0.9(7) . . . . ?
N21 C23 C24 C21 173.4(4) . . . . ?
N14 C23 C24 Br5' -145.3(4) . . . . ?
N21 C23 C24 Br5' 29.1(6) . . . . ?
C26 N15 C25 C28 -0.3(7) . . . . ?
C26 N15 C25 N21 -175.2(4) . . . . ?
C23 N21 C25 N15 -124.0(5) . . . . ?
C37 N21 C25 N15 51.4(8) . . . . ?
C23 N21 C25 C28 61.1(7) . . . . ?
C37 N21 C25 C28 -123.4(6) . . . . ?
C27 N16 C26 N15 2.2(8) . . . . ?
C25 N15 C26 N16 -3.1(8) . . . . ?
C26 N16 C27 N22 178.4(4) . . . . ?
C26 N16 C27 C28 2.1(7) . . . . ?
C29 N22 C27 N16 141.4(5) . . . . ?
C38 N22 C27 N16 -47.2(6) . . . . ?
C29 N22 C27 C28 -42.4(7) . . . . ?
C38 N22 C27 C28 129.0(5) . . . . ?
N15 C25 C28 C27 4.1(7) . . . . ?
N21 C25 C28 C27 178.7(4) . . . . ?
N15 C25 C28 Br4 -168.7(4) . . . . ?
N21 C25 C28 Br4 5.9(6) . . . . ?
N16 C27 C28 C25 -5.0(7) . . . . ?
N22 C27 C28 C25 178.9(4) . . . . ?
N16 C27 C28 Br4 167.7(4) . . . . ?
N22 C27 C28 Br4 -8.4(6) . . . . ?
C30 N17 C29 N22 178.0(4) . . . . ?
C30 N17 C29 C32 3.2(7) . . . . ?
C27 N22 C29 N17 142.1(5) . . . . ?
C38 N22 C29 N17 -29.2(6) . . . . ?
C27 N22 C29 C32 -43.3(7) . . . . ?
C38 N22 C29 C32 145.5(5) . . . . ?
C31 N18 C30 N17 -4.0(8) . . . . ?
C29 N17 C30 N18 2.4(8) . . . . ?
C30 N18 C31 N23 -175.4(5) . . . . ?
C30 N18 C31 C32 0.0(7) . . . . ?
C33 N23 C31 N18 -155.6(5) . . . . ?
C39 N23 C31 N18 16.1(7) . . . . ?
C33 N23 C31 C32 29.2(7) . . . . ?
C39 N23 C31 C32 -159.1(5) . . . . ?
N17 C29 C32 C31 -6.8(7) . . . . ?
N22 C29 C32 C31 178.8(4) . . . . ?
N17 C29 C32 Br5 162.7(4) . . . . ?
N22 C29 C32 Br5 -11.7(6) . . . . ?
N18 C31 C32 C29 5.1(7) . . . . ?
N23 C31 C32 C29 180.0(4) . . . . ?
N18 C31 C32 Br5 -164.1(4) . . . . ?
N23 C31 C32 Br5 10.8(7) . . . . ?
C34 N19 C33 C36 -5.3(7) . . . . ?
C34 N19 C33 N23 179.4(4) . . . . ?
C31 N23 C33 N19 -125.5(5) . . . . ?
C39 N23 C33 N19 62.5(6) . . . . ?
C31 N23 C33 C36 59.2(7) . . . . ?
C39 N23 C33 C36 -112.8(6) . . . . ?
C33 N19 C34 N20 -2.1(8) . . . . ?
C35 N20 C34 N19 4.9(8) . . . . ?
C34 N20 C35 N24 174.1(4) . . . . ?
C34 N20 C35 C36 -0.3(7) . . . . ?
C21 N24 C35 N20 139.3(5) . . . . ?
C40 N24 C35 N20 -20.8(6) . . . . ?
C21 N24 C35 C36 -46.5(7) . . . . ?
C40 N24 C35 C36 153.3(5) . . . . ?
N19 C33 C36 C35 9.3(7) . . . . ?
N23 C33 C36 C35 -175.7(4) . . . . ?
N19 C33 C36 Br6 -164.8(4) . . . . ?
N23 C33 C36 Br6 10.2(6) . . . . ?
N20 C35 C36 C33 -6.1(7) . . . . ?
N24 C35 C36 C33 179.9(4) . . . . ?
N20 C35 C36 Br6 167.8(3) . . . . ?
N24 C35 C36 Br6 -6.2(7) . . . . ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.500 210 28 ' '
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139091398
