#------------------------------------------------------------------------------
#$Date: 2025-08-21 23:26:11 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301853 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/20/7102073.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_7102073
loop_
_publ_author_name
'Bond, Andrew D'
'Jørgensen, Wendie H'
'Pløger, Jane M'
_publ_section_title
;
 Hydrogen-bonded cubanes and ladder fragments by analogy with the
 inorganic solid state.
;
_journal_issue                   31
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3273
_journal_page_last               3275
_journal_paper_doi               10.1039/b706422e
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H18 N +, Br -, 0.25(C H Cl3)'
_chemical_formula_sum            'C19.25 H18.25 Br Cl0.75 N'
_chemical_formula_weight         370.10
_space_group_IT_number           143
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 3'
_symmetry_space_group_name_H-M   'P 3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            8
_cell_length_a                   14.3387(3)
_cell_length_b                   14.3387(3)
_cell_length_c                   20.4479(8)
_cell_measurement_reflns_used    7442
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      25.39
_cell_measurement_theta_min      2.58
_cell_volume                     3640.82(18)
_computing_cell_refinement       'SAINT v.7.06a (Bruker, 2003)'
_computing_data_collection       'APEX2 v.1.0-22 (Bruker Nonius, 2004)'
_computing_data_reduction        'SAINT v.7.06a'
_computing_molecular_graphics    'SHELXTL v.6.10'
_computing_publication_material  'SHELXTL v.6.10'
_computing_structure_refinement  'SHELXTL v.6.10'
_computing_structure_solution    'SHELXTL v.6.10 (Sheldrick, 2000)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker-Nonius X8APEX-II CCD'
_diffrn_measurement_method       'thin-slice ω and φ scans'
_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  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            58037
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         3.84
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.364
_exptl_absorpt_correction_T_max  0.798
_exptl_absorpt_correction_T_min  0.618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.10 (Sheldrick, 2003)
Ratio of minimum to maximum apparent transmission: 0.775824
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1508
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.805
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.116
_refine_ls_abs_structure_details 'Flack (1983), 4565 Friedel pairs'
_refine_ls_abs_structure_Flack   0.081(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     529
_refine_ls_number_reflns         9521
_refine_ls_number_restraints     331
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0630
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0967P)²+13.2783P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1778
_refine_ls_wR_factor_ref         0.1833
_reflns_number_gt                8176
_reflns_number_total             9521
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b706422e.txt
_cod_data_source_block           2
_cod_database_code               7102073
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, 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
Br1 Br 0.0000 0.0000 0.96958(6) 0.0351(3) Uani 1 3 d S
Br2 Br 0.00737(8) 0.19714(7) 0.77444(4) 0.0512(3) Uani 1 1 d .
Br3 Br 0.3333 0.6667 0.18148(6) 0.0320(3) Uani 1 3 d S
Br4 Br 0.15967(6) 0.69986(6) 0.37209(4) 0.03731(19) Uani 1 1 d .
N1 N 0.0000 0.0000 0.6816(5) 0.033(2) Uani 1 3 d S
H1A H 0.0006 0.0601 0.6964 0.049 Uiso 1 1 d R
C11 C 0.0000 0.0000 0.6076(6) 0.033(3) Uani 1 3 d SU
C12 C 0.1005(7) 0.1013(7) 0.5847(4) 0.0391(18) Uani 1 1 d U
C13 C 0.0981(8) 0.1621(8) 0.5307(5) 0.053(2) Uani 1 1 d U
H13 H 0.0312 0.1424 0.5105 0.064 Uiso 1 1 calc R
C14 C 0.1883(9) 0.2466(10) 0.5076(6) 0.067(3) Uani 1 1 d U
H14A H 0.1831 0.2846 0.4710 0.081 Uiso 1 1 calc R
C15 C 0.2899(9) 0.2812(8) 0.5352(5) 0.060(3) Uani 1 1 d U
H15A H 0.3533 0.3414 0.5186 0.072 Uiso 1 1 calc R
C16 C 0.2923(8) 0.2227(9) 0.5879(5) 0.061(3) Uani 1 1 d U
H16A H 0.3593 0.2434 0.6084 0.073 Uiso 1 1 calc R
C17 C 0.2014(7) 0.1359(8) 0.6115(5) 0.050(2) Uani 1 1 d U
H17A H 0.2075 0.0976 0.6476 0.060 Uiso 1 1 calc R
N2 N 0.1874(5) 0.1816(5) 0.8676(4) 0.0445(16) Uani 1 1 d .
H2A H 0.1521 0.1363 0.9014 0.067 Uiso 1 1 calc R
H2B H 0.1987 0.1446 0.8353 0.067 Uiso 1 1 calc R
H2C H 0.1469 0.2092 0.8517 0.067 Uiso 1 1 calc R
C21 C 0.2948(6) 0.2727(7) 0.8914(4) 0.0443(19) Uani 1 1 d U
C22 C 0.3524(8) 0.3482(9) 0.8330(5) 0.059(2) Uani 1 1 d U
C23 C 0.4386(8) 0.4396(8) 0.8419(5) 0.063(3) Uani 1 1 d U
H23A H 0.4600 0.4620 0.8857 0.075 Uiso 1 1 calc R
C24 C 0.5035(12) 0.5090(11) 0.7917(7) 0.090(4) Uani 1 1 d U
H24A H 0.5717 0.5697 0.8015 0.108 Uiso 1 1 calc R
C25 C 0.4678(12) 0.4880(11) 0.7299(7) 0.085(4) Uani 1 1 d U
H25A H 0.5064 0.5371 0.6957 0.102 Uiso 1 1 calc R
C26 C 0.3741(12) 0.3936(11) 0.7174(7) 0.087(4) Uani 1 1 d U
H26A H 0.3487 0.3765 0.6737 0.104 Uiso 1 1 calc R
C27 C 0.3136(10) 0.3201(11) 0.7690(6) 0.073(3) Uani 1 1 d U
H27A H 0.2493 0.2545 0.7600 0.088 Uiso 1 1 calc R
C28 C 0.3473(8) 0.2157(7) 0.9208(4) 0.052(2) Uani 1 1 d U
C29 C 0.4395(10) 0.2272(10) 0.8912(7) 0.079(3) Uani 1 1 d U
H29A H 0.4659 0.2660 0.8515 0.095 Uiso 1 1 calc R
C210 C 0.4933(12) 0.1781(12) 0.9232(9) 0.096(4) Uani 1 1 d U
H21A H 0.5602 0.1901 0.9064 0.115 Uiso 1 1 calc R
C211 C 0.4492(11) 0.1125(11) 0.9791(7) 0.083(4) Uani 1 1 d U
H21B H 0.4851 0.0790 0.9986 0.100 Uiso 1 1 calc R
C212 C 0.3547(9) 0.0974(9) 1.0048(6) 0.067(3) Uani 1 1 d U
H21C H 0.3213 0.0504 1.0408 0.081 Uiso 1 1 calc R
C213 C 0.3097(7) 0.1534(8) 0.9765(5) 0.055(2) Uani 1 1 d U
H21D H 0.2480 0.1485 0.9970 0.066 Uiso 1 1 calc R
C214 C 0.2757(7) 0.3413(6) 0.9400(4) 0.0439(19) Uani 1 1 d U
C215 C 0.1938(8) 0.3652(7) 0.9299(5) 0.052(2) Uani 1 1 d U
H21E H 0.1432 0.3294 0.8959 0.063 Uiso 1 1 calc R
C216 C 0.1837(8) 0.4429(9) 0.9699(5) 0.064(3) Uani 1 1 d U
H21F H 0.1280 0.4595 0.9630 0.077 Uiso 1 1 calc R
C217 C 0.2607(8) 0.4921(8) 1.0191(5) 0.057(2) Uani 1 1 d U
H21H H 0.2587 0.5449 1.0462 0.068 Uiso 1 1 calc R
C218 C 0.3368(8) 0.4663(7) 1.0288(4) 0.054(2) Uani 1 1 d U
H21I H 0.3885 0.5027 1.0622 0.065 Uiso 1 1 calc R
C219 C 0.3440(7) 0.3873(6) 0.9917(4) 0.0407(17) Uani 1 1 d U
H21G H 0.3955 0.3664 1.0024 0.049 Uiso 1 1 calc R
N3 N 0.5043(5) 0.6357(5) 0.2783(4) 0.0337(13) Uani 1 1 d .
H3A H 0.5363 0.6959 0.3037 0.050 Uiso 1 1 calc R
H3B H 0.4523 0.5802 0.3018 0.050 Uiso 1 1 calc R
H3C H 0.4741 0.6482 0.2427 0.050 Uiso 1 1 calc R
C31 C 0.5866(5) 0.6076(5) 0.2566(4) 0.0309(15) Uani 1 1 d DU
C32 C 0.6487(4) 0.5972(6) 0.3140(4) 0.0409(17) Uani 1 1 d DU
C33 C 0.6726(8) 0.5129(10) 0.3149(7) 0.088(4) Uani 1 1 d DU
H33A H 0.6513 0.4609 0.2809 0.105 Uiso 1 1 calc R
C34 C 0.7275(10) 0.5121(13) 0.3673(8) 0.120(6) Uani 1 1 d DU
H34A H 0.7458 0.4570 0.3697 0.144 Uiso 1 1 calc R
C35 C 0.7598(8) 0.5838(12) 0.4178(6) 0.106(5) Uani 1 1 d DU
H35A H 0.7979 0.5767 0.4537 0.128 Uiso 1 1 calc R
C36 C 0.7393(7) 0.6579(8) 0.4168(5) 0.062(3) Uani 1 1 d DU
H36A H 0.7627 0.7085 0.4517 0.075 Uiso 1 1 calc R
C37 C 0.6829(7) 0.6671(8) 0.3655(4) 0.059(2) Uani 1 1 d DU
H37A H 0.6671 0.7241 0.3658 0.071 Uiso 1 1 calc R
C38 C 0.5338(6) 0.5081(6) 0.2128(4) 0.0348(17) Uani 1 1 d U
C39 C 0.5840(8) 0.4907(8) 0.1598(6) 0.065(3) Uani 1 1 d U
H39A H 0.6525 0.5471 0.1460 0.077 Uiso 1 1 calc R
C310 C 0.5385(10) 0.3964(9) 0.1277(6) 0.070(3) Uani 1 1 d U
H31A H 0.5788 0.3857 0.0947 0.085 Uiso 1 1 calc R
C311 C 0.4371(9) 0.3161(7) 0.1406(5) 0.056(2) Uani 1 1 d U
H31B H 0.4061 0.2488 0.1185 0.067 Uiso 1 1 calc R
C312 C 0.3812(8) 0.3377(8) 0.1879(6) 0.064(3) Uani 1 1 d U
H31C H 0.3071 0.2878 0.1951 0.077 Uiso 1 1 calc R
C313 C 0.4316(7) 0.4302(8) 0.2244(5) 0.058(2) Uani 1 1 d U
H31D H 0.3930 0.4397 0.2590 0.070 Uiso 1 1 calc R
C314 C 0.6731(6) 0.7039(6) 0.2141(4) 0.0330(16) Uani 1 1 d U
C315 C 0.6435(7) 0.7562(7) 0.1684(4) 0.047(2) Uani 1 1 d U
H31E H 0.5699 0.7368 0.1644 0.057 Uiso 1 1 calc R
C316 C 0.7173(8) 0.8336(9) 0.1298(5) 0.061(2) Uani 1 1 d U
H31F H 0.6942 0.8684 0.0997 0.073 Uiso 1 1 calc R
C317 C 0.8236(7) 0.8646(6) 0.1320(4) 0.0424(19) Uani 1 1 d U
H31G H 0.8740 0.9182 0.1033 0.051 Uiso 1 1 calc R
C318 C 0.8558(6) 0.8142(7) 0.1782(4) 0.0449(19) Uani 1 1 d U
H31H H 0.9294 0.8338 0.1816 0.054 Uiso 1 1 calc R
C319 C 0.7806(6) 0.7365(7) 0.2185(4) 0.0420(18) Uani 1 1 d U
H31I H 0.8037 0.7044 0.2505 0.050 Uiso 1 1 calc R
N4 N 0.3333 0.6667 0.4625(6) 0.036(3) Uani 1 3 d S
H4A H 0.2718 0.6631 0.4477 0.054 Uiso 1 1 d R
C41 C 0.3333 0.6667 0.5353(7) 0.040(3) Uani 1 3 d SU
C42 C 0.2334(7) 0.5621(7) 0.5582(4) 0.0423(19) Uani 1 1 d U
C43 C 0.2390(9) 0.4999(9) 0.6064(5) 0.063(3) Uani 1 1 d U
H43A H 0.3068 0.5182 0.6251 0.075 Uiso 1 1 calc R
C44 C 0.1448(10) 0.4084(9) 0.6289(6) 0.074(3) Uani 1 1 d U
H44A H 0.1476 0.3659 0.6637 0.089 Uiso 1 1 calc R
C45 C 0.0524(11) 0.3832(11) 0.6004(7) 0.081(4) Uani 1 1 d U
H45A H -0.0105 0.3221 0.6167 0.097 Uiso 1 1 calc R
C46 C 0.0391(10) 0.4387(10) 0.5481(6) 0.076(3) Uani 1 1 d U
H46A H -0.0285 0.4166 0.5279 0.092 Uiso 1 1 calc R
C47 C 0.1355(9) 0.5304(9) 0.5285(6) 0.065(3) Uani 1 1 d U
H47A H 0.1331 0.5724 0.4933 0.078 Uiso 1 1 calc R
Cl1 Cl 0.0172(3) 0.8922(3) 0.3382(2) 0.1007(11) Uani 1 1 d D
Cl2 Cl 0.2713(5) 0.7395(6) 0.7776(3) 0.162(2) Uani 1 1 d D
C100 C 0.0000 1.0000 0.3099(11) 0.101(7) Uani 1 3 d SDU
H10A H 0.0000 1.0000 0.2610 0.121 Uiso 1 3 d SR
C101 C 0.3333 0.6667 0.8112(14) 0.229(12) Uani 1 3 d SDU
H10B H 0.3333 0.6667 0.8601 0.275 Uiso 1 3 calc SR
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C11 N1 H1A 109.5 . .
N1 C11 C12 107.9(5) . .
N1 C11 C12 107.9(5) . 3
C12 C11 C12 111.0(5) . 3
N1 C11 C12 107.9(5) . 2
C12 C11 C12 111.0(5) . 2
C12 C11 C12 111.0(5) 3 2
C17 C12 C13 115.4(8) . .
C17 C12 C11 122.7(8) . .
C13 C12 C11 121.7(8) . .
C14 C13 C12 121.5(10) . .
C14 C13 H13 119.2 . .
C12 C13 H13 119.2 . .
C13 C14 C15 122.6(10) . .
C13 C14 H14A 118.7 . .
C15 C14 H14A 118.7 . .
C16 C15 C14 116.0(9) . .
C16 C15 H15A 122.0 . .
C14 C15 H15A 122.0 . .
C17 C16 C15 122.0(10) . .
C17 C16 H16A 119.0 . .
C15 C16 H16A 119.0 . .
C16 C17 C12 122.4(9) . .
C16 C17 H17A 118.8 . .
C12 C17 H17A 118.8 . .
C21 N2 H2A 109.5 . .
C21 N2 H2B 109.5 . .
H2A N2 H2B 109.5 . .
C21 N2 H2C 109.5 . .
H2A N2 H2C 109.5 . .
H2B N2 H2C 109.5 . .
C28 C21 C214 113.4(7) . .
C28 C21 N2 103.4(7) . .
C214 C21 N2 109.5(7) . .
C28 C21 C22 117.3(8) . .
C214 C21 C22 105.0(7) . .
N2 C21 C22 108.2(7) . .
C23 C22 C27 117.7(10) . .
C23 C22 C21 120.6(9) . .
C27 C22 C21 121.7(9) . .
C22 C23 C24 125.1(12) . .
C22 C23 H23A 117.4 . .
C24 C23 H23A 117.4 . .
C25 C24 C23 119.0(13) . .
C25 C24 H24A 120.5 . .
C23 C24 H24A 120.5 . .
C24 C25 C26 118.3(13) . .
C24 C25 H25A 120.9 . .
C26 C25 H25A 120.9 . .
C25 C26 C27 121.3(13) . .
C25 C26 H26A 119.3 . .
C27 C26 H26A 119.3 . .
C22 C27 C26 118.0(12) . .
C22 C27 H27A 121.0 . .
C26 C27 H27A 121.0 . .
C213 C28 C29 118.6(10) . .
C213 C28 C21 123.3(8) . .
C29 C28 C21 118.2(9) . .
C28 C29 C210 117.2(12) . .
C28 C29 H29A 121.4 . .
C210 C29 H29A 121.4 . .
C211 C210 C29 121.5(12) . .
C211 C210 H21A 119.2 . .
C29 C210 H21A 119.2 . .
C212 C211 C210 119.7(11) . .
C212 C211 H21B 120.1 . .
C210 C211 H21B 120.1 . .
C211 C212 C213 117.4(11) . .
C211 C212 H21C 121.3 . .
C213 C212 H21C 121.3 . .
C28 C213 C212 125.2(10) . .
C28 C213 H21D 117.4 . .
C212 C213 H21D 117.4 . .
C219 C214 C215 119.0(8) . .
C219 C214 C21 120.1(8) . .
C215 C214 C21 120.7(7) . .
C214 C215 C216 121.9(8) . .
C214 C215 H21E 119.1 . .
C216 C215 H21E 119.1 . .
C217 C216 C215 116.0(9) . .
C217 C216 H21F 122.0 . .
C215 C216 H21F 122.0 . .
C218 C217 C216 121.1(9) . .
C218 C217 H21H 119.4 . .
C216 C217 H21H 119.4 . .
C217 C218 C219 122.9(9) . .
C217 C218 H21I 118.5 . .
C219 C218 H21I 118.5 . .
C214 C219 C218 118.7(8) . .
C214 C219 H21G 120.6 . .
C218 C219 H21G 120.6 . .
C31 N3 H3A 109.5 . .
C31 N3 H3B 109.5 . .
H3A N3 H3B 109.5 . .
C31 N3 H3C 109.5 . .
H3A N3 H3C 109.5 . .
H3B N3 H3C 109.5 . .
N3 C31 C32 112.1(6) . .
N3 C31 C38 109.7(6) . .
C32 C31 C38 113.7(6) . .
N3 C31 C314 108.0(5) . .
C32 C31 C314 105.5(4) . .
C38 C31 C314 107.5(6) . .
C37 C32 C33 117.8(9) . .
C37 C32 C31 122.4(7) . .
C33 C32 C31 119.8(9) . .
C34 C33 C32 114.5(13) . .
C34 C33 H33A 122.8 . .
C32 C33 H33A 122.8 . .
C33 C34 C35 125.6(14) . .
C33 C34 H34A 117.2 . .
C35 C34 H34A 117.2 . .
C36 C35 C34 119.9(12) . .
C36 C35 H35A 120.1 . .
C34 C35 H35A 120.1 . .
C35 C36 C37 120.0(11) . .
C35 C36 H36A 120.0 . .
C37 C36 H36A 120.0 . .
C32 C37 C36 122.2(9) . .
C32 C37 H37A 118.9 . .
C36 C37 H37A 118.9 . .
C313 C38 C39 115.8(8) . .
C313 C38 C31 119.9(7) . .
C39 C38 C31 124.4(8) . .
C310 C39 C38 121.8(9) . .
C310 C39 H39A 119.1 . .
C38 C39 H39A 119.1 . .
C39 C310 C311 122.4(9) . .
C39 C310 H31A 118.8 . .
C311 C310 H31A 118.8 . .
C310 C311 C312 116.1(8) . .
C310 C311 H31B 121.9 . .
C312 C311 H31B 121.9 . .
C313 C312 C311 120.8(10) . .
C313 C312 H31C 119.6 . .
C311 C312 H31C 119.6 . .
C38 C313 C312 122.4(9) . .
C38 C313 H31D 118.8 . .
C312 C313 H31D 118.8 . .
C319 C314 C315 117.0(7) . .
C319 C314 C31 121.3(7) . .
C315 C314 C31 121.6(7) . .
C316 C315 C314 120.9(8) . .
C316 C315 H31E 119.5 . .
C314 C315 H31E 119.5 . .
C315 C316 C317 122.9(9) . .
C315 C316 H31F 118.6 . .
C317 C316 H31F 118.6 . .
C316 C317 C318 117.3(8) . .
C316 C317 H31G 121.3 . .
C318 C317 H31G 121.3 . .
C319 C318 C317 119.8(7) . .
C319 C318 H31H 120.1 . .
C317 C318 H31H 120.1 . .
C314 C319 C318 122.0(8) . .
C314 C319 H31I 119.0 . .
C318 C319 H31I 119.0 . .
C41 N4 H4A 109.5 . .
N4 C41 C42 107.7(6) . 3_565
N4 C41 C42 107.7(6) . .
C42 C41 C42 111.1(6) 3_565 .
N4 C41 C42 107.7(6) . 2_665
C42 C41 C42 111.1(6) 3_565 2_665
C42 C41 C42 111.1(6) . 2_665
C43 C42 C47 119.2(9) . .
C43 C42 C41 121.9(9) . .
C47 C42 C41 118.9(8) . .
C42 C43 C44 120.2(10) . .
C42 C43 H43A 119.9 . .
C44 C43 H43A 119.9 . .
C45 C44 C43 118.3(12) . .
C45 C44 H44A 120.9 . .
C43 C44 H44A 120.9 . .
C44 C45 C46 125.7(13) . .
C44 C45 H45A 117.1 . .
C46 C45 H45A 117.1 . .
C45 C46 C47 113.5(12) . .
C45 C46 H46A 123.2 . .
C47 C46 H46A 123.2 . .
C42 C47 C46 122.8(11) . .
C42 C47 H47A 118.6 . .
C46 C47 H47A 118.6 . .
Cl1 C100 Cl1 110.0(7) 2_675 3_465
Cl1 C100 Cl1 110.0(7) 2_675 .
Cl1 C100 Cl1 110.0(7) 3_465 .
Cl1 C100 H10A 109.0 2_675 .
Cl1 C100 H10A 109.0 3_465 .
Cl1 C100 H10A 109.0 . .
Cl2 C101 Cl2 106.5(10) 2_665 3_565
Cl2 C101 Cl2 106.5(10) 2_665 .
Cl2 C101 Cl2 106.5(10) 3_565 .
Cl2 C101 H10B 112.3 2_665 .
Cl2 C101 H10B 112.3 3_565 .
Cl2 C101 H10B 112.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C11 1.513(16) .
N1 H1A 0.910 .
C11 C12 1.521(9) .
C11 C12 1.521(9) 3
C11 C12 1.521(9) 2
C12 C17 1.387(13) .
C12 C13 1.416(12) .
C13 C14 1.341(14) .
C13 H13 0.950 .
C14 C15 1.401(16) .
C14 H14A 0.950 .
C15 C16 1.376(15) .
C15 H15A 0.950 .
C16 C17 1.363(14) .
C16 H16A 0.950 .
C17 H17A 0.950 .
N2 C21 1.518(10) .
N2 H2A 0.910 .
N2 H2B 0.910 .
N2 H2C 0.910 .
C21 C28 1.487(14) .
C21 C214 1.516(12) .
C21 C22 1.544(13) .
C22 C23 1.288(14) .
C22 C27 1.400(15) .
C23 C24 1.409(15) .
C23 H23A 0.950 .
C24 C25 1.339(18) .
C24 H24A 0.950 .
C25 C26 1.373(19) .
C25 H25A 0.950 .
C26 C27 1.436(17) .
C26 H26A 0.950 .
C27 H27A 0.950 .
C28 C213 1.379(14) .
C28 C29 1.386(15) .
C29 C210 1.436(18) .
C29 H29A 0.950 .
C210 C211 1.41(2) .
C210 H21A 0.950 .
C211 C212 1.366(17) .
C211 H21B 0.950 .
C212 C213 1.384(14) .
C212 H21C 0.950 .
C213 H21D 0.950 .
C214 C219 1.367(11) .
C214 C215 1.393(13) .
C215 C216 1.446(14) .
C215 H21E 0.950 .
C216 C217 1.398(14) .
C216 H21F 0.950 .
C217 C218 1.331(14) .
C217 H21H 0.950 .
C218 C219 1.410(12) .
C218 H21I 0.950 .
C219 H21G 0.950 .
N3 C31 1.494(9) .
N3 H3A 0.910 .
N3 H3B 0.910 .
N3 H3C 0.910 .
C31 C32 1.524(10) .
C31 C38 1.527(10) .
C31 C314 1.577(10) .
C32 C37 1.365(13) .
C32 C33 1.413(14) .
C33 C34 1.334(18) .
C33 H33A 0.950 .
C34 C35 1.36(2) .
C34 H34A 0.950 .
C35 C36 1.236(18) .
C35 H35A 0.950 .
C36 C37 1.372(14) .
C36 H36A 0.950 .
C37 H37A 0.950 .
C38 C313 1.347(12) .
C38 C39 1.391(13) .
C39 C310 1.343(15) .
C39 H39A 0.950 .
C310 C311 1.355(15) .
C310 H31A 0.950 .
C311 C312 1.387(14) .
C311 H31B 0.950 .
C312 C313 1.370(13) .
C312 H31C 0.950 .
C313 H31D 0.950 .
C314 C319 1.372(11) .
C314 C315 1.391(11) .
C315 C316 1.342(13) .
C315 H31E 0.950 .
C316 C317 1.359(13) .
C316 H31F 0.950 .
C317 C318 1.399(12) .
C317 H31G 0.950 .
C318 C319 1.372(11) .
C318 H31H 0.950 .
C319 H31I 0.950 .
N4 C41 1.488(18) .
N4 H4A 0.910 .
C41 C42 1.541(9) 3_565
C41 C42 1.541(9) .
C41 C42 1.541(9) 2_665
C42 C43 1.358(13) .
C42 C47 1.382(14) .
C43 C44 1.409(16) .
C43 H43A 0.950 .
C44 C45 1.323(18) .
C44 H44A 0.950 .
C45 C46 1.401(19) .
C45 H45A 0.950 .
C46 C47 1.408(15) .
C46 H46A 0.950 .
C47 H47A 0.950 .
Cl1 C100 1.780(7) .
Cl2 C101 1.811(10) .
C100 Cl1 1.780(7) 2_675
C100 Cl1 1.780(7) 3_465
C100 H10A 1.000 .
C101 Cl2 1.811(10) 2_665
C101 Cl2 1.811(10) 3_565
C101 H10B 1.000 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Br2 0.91 2.49 3.363(6) 159.6 .
N2 H2A Br1 0.91 2.50 3.369(7) 159.7 .
N2 H2C Br2 0.91 2.49 3.304(8) 149.6 .
N2 H2B Br2 0.91 2.46 3.326(8) 159.8 3
N3 H3C Br3 0.91 2.50 3.349(7) 155.6 .
N3 H3C Br3 0.91 2.50 3.349(7) 155.6 2_665
N3 H3C Br3 0.91 2.50 3.349(7) 155.6 3_565
N4 H4A Br4 0.91 2.47 3.321(6) 155.9 .
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
N1 C11 C12 C17 45.5(8) .
C12 C11 C12 C17 -72.5(13) 3
C12 C11 C12 C17 163.6(8) 2
N1 C11 C12 C13 -139.7(7) .
C12 C11 C12 C13 102.2(7) 3
C12 C11 C12 C13 -21.6(12) 2
C17 C12 C13 C14 0.3(14) .
C11 C12 C13 C14 -174.9(9) .
C12 C13 C14 C15 -0.7(17) .
C13 C14 C15 C16 0.3(17) .
C14 C15 C16 C17 0.4(17) .
C15 C16 C17 C12 -0.8(17) .
C13 C12 C17 C16 0.4(14) .
C11 C12 C17 C16 175.5(9) .
C28 C21 C22 C23 -73.0(12) .
C214 C21 C22 C23 53.8(12) .
N2 C21 C22 C23 170.6(10) .
C28 C21 C22 C27 106.7(11) .
C214 C21 C22 C27 -126.4(11) .
N2 C21 C22 C27 -9.6(14) .
C27 C22 C23 C24 -7.0(18) .
C21 C22 C23 C24 172.8(11) .
C22 C23 C24 C25 10(2) .
C23 C24 C25 C26 -6(2) .
C24 C25 C26 C27 2(2) .
C23 C22 C27 C26 1.7(17) .
C21 C22 C27 C26 -178.0(11) .
C25 C26 C27 C22 1(2) .
C214 C21 C28 C213 51.6(11) .
N2 C21 C28 C213 -66.8(10) .
C22 C21 C28 C213 174.2(9) .
C214 C21 C28 C29 -127.5(9) .
N2 C21 C28 C29 114.1(10) .
C22 C21 C28 C29 -4.9(12) .
C213 C28 C29 C210 -3.7(17) .
C21 C28 C29 C210 175.5(11) .
C28 C29 C210 C211 6(2) .
C29 C210 C211 C212 -2(2) .
C210 C211 C212 C213 -3.7(19) .
C29 C28 C213 C212 -2.2(16) .
C21 C28 C213 C212 178.7(9) .
C211 C212 C213 C28 6.0(17) .
C28 C21 C214 C219 30.4(11) .
N2 C21 C214 C219 145.3(8) .
C22 C21 C214 C219 -98.8(9) .
C28 C21 C214 C215 -154.6(8) .
N2 C21 C214 C215 -39.7(11) .
C22 C21 C214 C215 76.2(10) .
C219 C214 C215 C216 4.4(14) .
C21 C214 C215 C216 -170.7(9) .
C214 C215 C216 C217 -0.2(15) .
C215 C216 C217 C218 -1.3(15) .
C216 C217 C218 C219 -1.3(16) .
C215 C214 C219 C218 -6.9(12) .
C21 C214 C219 C218 168.2(8) .
C217 C218 C219 C214 5.6(14) .
N3 C31 C32 C37 -41.4(6) .
C38 C31 C32 C37 -166.5(6) .
C314 C31 C32 C37 75.9(6) .
N3 C31 C32 C33 138.7(6) .
C38 C31 C32 C33 13.5(6) .
C314 C31 C32 C33 -104.0(6) .
C37 C32 C33 C34 -0.2(4) .
C31 C32 C33 C34 179.7(3) .
C32 C33 C34 C35 0.5(6) .
C33 C34 C35 C36 -0.9(9) .
C34 C35 C36 C37 1.0(8) .
C33 C32 C37 C36 0.4(6) .
C31 C32 C37 C36 -179.6(4) .
C35 C36 C37 C32 -0.8(8) .
N3 C31 C38 C313 -34.2(10) .
C32 C31 C38 C313 92.2(8) .
C314 C31 C38 C313 -151.4(8) .
N3 C31 C38 C39 145.5(8) .
C32 C31 C38 C39 -88.1(9) .
C314 C31 C38 C39 28.3(10) .
C313 C38 C39 C310 -8.2(16) .
C31 C38 C39 C310 172.1(10) .
C38 C39 C310 C311 6.3(19) .
C39 C310 C311 C312 1.8(18) .
C310 C311 C312 C313 -7.6(17) .
C39 C38 C313 C312 2.3(15) .
C31 C38 C313 C312 -178.0(9) .
C311 C312 C313 C38 5.6(18) .
N3 C31 C314 C319 141.2(7) .
C32 C31 C314 C319 21.1(9) .
C38 C31 C314 C319 -100.6(8) .
N3 C31 C314 C315 -41.8(10) .
C32 C31 C314 C315 -161.9(7) .
C38 C31 C314 C315 76.4(9) .
C319 C314 C315 C316 1.2(13) .
C31 C314 C315 C316 -176.0(8) .
C314 C315 C316 C317 1.0(16) .
C315 C316 C317 C318 -1.8(15) .
C316 C317 C318 C319 0.5(13) .
C315 C314 C319 C318 -2.5(12) .
C31 C314 C319 C318 174.6(7) .
C317 C318 C319 C314 1.7(13) .
N4 C41 C42 C43 134.3(9) .
C42 C41 C42 C43 -107.9(8) 3_565
C42 C41 C42 C43 16.5(14) 2_665
N4 C41 C42 C47 -45.2(9) .
C42 C41 C42 C47 72.6(14) 3_565
C42 C41 C42 C47 -163.0(9) 2_665
C47 C42 C43 C44 -4.4(17) .
C41 C42 C43 C44 176.1(10) .
C42 C43 C44 C45 2.3(19) .
C43 C44 C45 C46 1(2) .
C44 C45 C46 C47 -2(2) .
C43 C42 C47 C46 3.3(18) .
C41 C42 C47 C46 -177.1(11) .
C45 C46 C47 C42 -0.1(19) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139180044
