#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/18/4501820.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_4501820
loop_
_publ_author_name
'Raatikainen, Kari'
'Rissanen, Kari'
_publ_section_title
;
 Modulation of N···I
 and+N−H···Cl−···I
 Halogen Bonding: Folding, Inclusion, and Self-Assembly of Tri- and
 Tetraamino Piperazine Cyclophanes
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3638
_journal_paper_doi               10.1021/cg100516t
_journal_volume                  10
_journal_year                    2010
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C36 H51 N9, C6 F4 I2, 4(C H4 O)'
_chemical_formula_sum            'C46 H67 F4 I2 N9 O4'
_chemical_formula_weight         1139.89
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-03-09T10:40:36-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 103.455(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.9697(4)
_cell_length_b                   26.6758(9)
_cell_length_c                   10.5487(3)
_cell_measurement_reflns_used    15915
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.91
_cell_measurement_wavelength     0.71073
_cell_volume                     5191.5(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.340591E-1
_diffrn_orient_matrix_UB_12      -0.251442E-1
_diffrn_orient_matrix_UB_13      -0.231035E-1
_diffrn_orient_matrix_UB_21      -0.287975E-1
_diffrn_orient_matrix_UB_22      0
_diffrn_orient_matrix_UB_23      -0.923627E-1
_diffrn_orient_matrix_UB_31      0.30801E-1
_diffrn_orient_matrix_UB_32      0.278039E-1
_diffrn_orient_matrix_UB_33      -0.208934E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4589
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         3.02
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    1.275
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2320
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.49(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     615
_refine_ls_number_reflns         4589
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+16.9322P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0496
_refine_ls_wR_factor_ref         0.0506
_reflns_number_gt                4415
_reflns_number_total             4589
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg100516t_si_001.cif
_cod_data_source_block           1-F4DIB
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4501820
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.3597(4) 0.7114(3) 0.0943(7) 0.0350(17) Uani 1 1 d .
C2 C 0.3542(4) 0.6924(3) -0.0285(8) 0.0386(18) Uani 1 1 d .
H2 H 0.3834 0.706 -0.0821 0.046 Uiso 1 1 calc R
C3 C 0.3063(4) 0.6534(3) -0.0758(7) 0.0394(19) Uani 1 1 d .
H3 H 0.3013 0.6411 -0.1619 0.047 Uiso 1 1 calc R
C4 C 0.2667(4) 0.6332(3) 0.0048(8) 0.0335(18) Uani 1 1 d .
H4 H 0.2336 0.6069 -0.028 0.04 Uiso 1 1 calc R
C5 C 0.2724(4) 0.6494(3) 0.1325(7) 0.0274(17) Uani 1 1 d .
C6 C 0.3188(4) 0.6900(3) 0.1769(7) 0.0286(17) Uani 1 1 d .
C7 C 0.2315(4) 0.6233(3) 0.2180(8) 0.0282(17) Uani 1 1 d .
H7A H 0.2226 0.6476 0.2835 0.034 Uiso 1 1 calc R
H7B H 0.1838 0.6131 0.1639 0.034 Uiso 1 1 calc R
N8 N 0.2673(4) 0.5782(3) 0.2879(6) 0.0259(15) Uani 1 1 d .
C9 C 0.2831(5) 0.5398(3) 0.1996(9) 0.028(2) Uani 1 1 d .
H9A H 0.3148 0.5541 0.1464 0.034 Uiso 1 1 calc R
H9B H 0.2374 0.5289 0.1397 0.034 Uiso 1 1 calc R
C10 C 0.3202(4) 0.4948(3) 0.2745(6) 0.0280(15) Uani 1 1 d .
H10A H 0.2883 0.4796 0.326 0.034 Uiso 1 1 calc R
H10B H 0.3306 0.4693 0.2133 0.034 Uiso 1 1 calc R
N11 N 0.3875(3) 0.5117(2) 0.3610(5) 0.0267(12) Uani 1 1 d .
C12 C 0.3698(4) 0.5465(3) 0.4552(7) 0.0310(19) Uani 1 1 d .
H12A H 0.4146 0.5563 0.5192 0.037 Uiso 1 1 calc R
H12B H 0.337 0.53 0.5029 0.037 Uiso 1 1 calc R
C13 C 0.3339(4) 0.5922(3) 0.3873(7) 0.0285(17) Uani 1 1 d .
H13A H 0.3209 0.6152 0.452 0.034 Uiso 1 1 calc R
H13B H 0.3679 0.6099 0.3445 0.034 Uiso 1 1 calc R
C14 C 0.4335(3) 0.4692(2) 0.4197(6) 0.0312(13) Uani 1 1 d .
H14A H 0.4027 0.4432 0.4464 0.037 Uiso 1 1 calc R
H14B H 0.4686 0.4809 0.499 0.037 Uiso 1 1 calc R
C15 C 0.4743(3) 0.4464(2) 0.3277(5) 0.0274(12) Uani 1 1 d .
C16 C 0.4677(3) 0.3960(2) 0.2963(6) 0.0386(14) Uani 1 1 d .
H16 H 0.4344 0.376 0.3291 0.046 Uiso 1 1 calc R
C17 C 0.5087(3) 0.3738(2) 0.2172(6) 0.0410(14) Uani 1 1 d .
H17 H 0.5032 0.3392 0.1954 0.049 Uiso 1 1 calc R
C18 C 0.5574(3) 0.4031(2) 0.1716(6) 0.0337(13) Uani 1 1 d .
H18 H 0.5867 0.388 0.1203 0.04 Uiso 1 1 calc R
C19 C 0.5649(3) 0.4538(2) 0.1981(5) 0.0249(11) Uani 1 1 d .
C20 C 0.5220(3) 0.47649(19) 0.2757(4) 0.0254(12) Uani 1 1 d .
C21 C 0.6135(3) 0.4848(2) 0.1320(6) 0.0300(12) Uani 1 1 d .
H21A H 0.6457 0.4618 0.0979 0.036 Uiso 1 1 calc R
H21B H 0.5827 0.5025 0.0566 0.036 Uiso 1 1 calc R
N22 N 0.6584(3) 0.5219(2) 0.2172(5) 0.0247(12) Uani 1 1 d .
C23 C 0.7179(4) 0.4994(2) 0.3107(6) 0.0226(13) Uani 1 1 d .
H23A H 0.7511 0.4828 0.264 0.027 Uiso 1 1 calc R
H23B H 0.6989 0.4735 0.3613 0.027 Uiso 1 1 calc R
C24 C 0.7590(5) 0.5384(3) 0.4024(9) 0.0265(19) Uani 1 1 d .
H24A H 0.7268 0.5528 0.4545 0.032 Uiso 1 1 calc R
H24B H 0.8005 0.5223 0.4632 0.032 Uiso 1 1 calc R
N25 N 0.7857(3) 0.5787(2) 0.3304(6) 0.0215(13) Uani 1 1 d .
C26 C 0.7259(4) 0.6000(3) 0.2311(7) 0.0272(17) Uani 1 1 d .
H26A H 0.7451 0.6254 0.1796 0.033 Uiso 1 1 calc R
H26B H 0.6912 0.6168 0.2742 0.033 Uiso 1 1 calc R
C27 C 0.6866(4) 0.5587(3) 0.1400(6) 0.0261(14) Uani 1 1 d .
H27A H 0.6463 0.5734 0.0735 0.031 Uiso 1 1 calc R
H27B H 0.7206 0.5424 0.0946 0.031 Uiso 1 1 calc R
C28 C 0.8267(4) 0.6171(3) 0.4190(7) 0.0261(16) Uani 1 1 d .
H28A H 0.8405 0.6442 0.3655 0.031 Uiso 1 1 calc R
H28B H 0.872 0.6016 0.4695 0.031 Uiso 1 1 calc R
C29 C 0.7866(4) 0.6407(3) 0.5155(7) 0.0249(16) Uani 1 1 d .
C30 C 0.7968(4) 0.6182(2) 0.6357(6) 0.0246(15) Uani 1 1 d .
H30 H 0.8296 0.5909 0.6565 0.03 Uiso 1 1 calc R
C31 C 0.7597(4) 0.6350(2) 0.7285(7) 0.0344(16) Uani 1 1 d .
H31 H 0.7664 0.6193 0.8113 0.041 Uiso 1 1 calc R
C32 C 0.7134(4) 0.6751(3) 0.6951(7) 0.0385(18) Uani 1 1 d .
H32 H 0.6878 0.6868 0.7566 0.046 Uiso 1 1 calc R
C33 C 0.7026(4) 0.6989(3) 0.5771(7) 0.0326(17) Uani 1 1 d .
C34 C 0.7410(4) 0.6832(3) 0.4849(7) 0.0298(17) Uani 1 1 d .
C35 C 0.6545(4) 0.7453(3) 0.5562(7) 0.0432(17) Uani 1 1 d .
H35A H 0.6265 0.7462 0.6245 0.052 Uiso 1 1 calc R
H35B H 0.6858 0.7754 0.5672 0.052 Uiso 1 1 calc R
N36 N 0.6034(3) 0.74766(19) 0.4273(6) 0.0337(13) Uani 1 1 d .
C37 C 0.5575(4) 0.7923(2) 0.4204(8) 0.051(2) Uani 1 1 d .
H37A H 0.5885 0.8226 0.4351 0.061 Uiso 1 1 calc R
H37B H 0.5306 0.7907 0.4903 0.061 Uiso 1 1 calc R
C38 C 0.5049(4) 0.7963(2) 0.2914(8) 0.049(2) Uani 1 1 d .
H38A H 0.4741 0.8263 0.2908 0.059 Uiso 1 1 calc R
H38B H 0.5318 0.8004 0.2221 0.059 Uiso 1 1 calc R
N39 N 0.4589(3) 0.7516(2) 0.2642(6) 0.0345(13) Uani 1 1 d .
C40 C 0.5059(4) 0.7074(3) 0.2695(7) 0.0346(18) Uani 1 1 d .
H40A H 0.5342 0.7104 0.2019 0.041 Uiso 1 1 calc R
H40B H 0.4757 0.6768 0.2511 0.041 Uiso 1 1 calc R
C41 C 0.5564(4) 0.7031(3) 0.4006(7) 0.0320(17) Uani 1 1 d .
H41A H 0.5282 0.6999 0.4682 0.038 Uiso 1 1 calc R
H41B H 0.5866 0.6726 0.4038 0.038 Uiso 1 1 calc R
C42 C 0.4080(4) 0.7563(2) 0.1372(7) 0.0396(16) Uani 1 1 d .
H42A H 0.4361 0.7628 0.0706 0.048 Uiso 1 1 calc R
H42B H 0.3769 0.7859 0.1395 0.048 Uiso 1 1 calc R
N43 N 0.3233(4) 0.7115(3) 0.2976(7) 0.0391(16) Uani 1 1 d D
H43A H 0.361(3) 0.730(2) 0.331(6) 0.05 Uiso 1 1 d D
H43B H 0.299(3) 0.699(3) 0.349(6) 0.05 Uiso 1 1 d D
N44 N 0.5268(6) 0.52675(15) 0.3019(9) 0.0331(10) Uani 1 1 d D
H44A H 0.561(3) 0.541(3) 0.275(7) 0.05 Uiso 1 1 d D
H44B H 0.491(3) 0.544(3) 0.318(7) 0.05 Uiso 1 1 d D
N45 N 0.7327(4) 0.7071(3) 0.3677(7) 0.0336(14) Uani 1 1 d D
H45A H 0.759(4) 0.710(3) 0.312(6) 0.05 Uiso 1 1 d D
H45B H 0.705(3) 0.7328(18) 0.349(7) 0.05 Uiso 1 1 d D
I46 I 0.162416(16) 0.543056(17) 0.40771(2) 0.02960(12) Uani 1 1 d .
C47 C 0.0825(5) 0.5174(3) 0.5007(8) 0.0297(18) Uani 1 1 d .
C48 C 0.0607(5) 0.4683(3) 0.4961(8) 0.033(2) Uani 1 1 d .
F49 F 0.0918(3) 0.43428(18) 0.4284(5) 0.0387(11) Uani 1 1 d .
C50 C 0.0077(6) 0.4509(3) 0.5558(9) 0.028(2) Uani 1 1 d .
F51 F -0.0100(3) 0.4020(2) 0.5438(6) 0.0476(14) Uani 1 1 d .
C52 C -0.0244(4) 0.4827(3) 0.6256(7) 0.0253(17) Uani 1 1 d .
I53 I -0.107016(16) 0.457777(16) 0.71638(2) 0.02795(12) Uani 1 1 d .
C54 C -0.0038(4) 0.5328(3) 0.6364(8) 0.0256(18) Uani 1 1 d .
F55 F -0.0335(3) 0.56530(19) 0.7021(5) 0.0393(12) Uani 1 1 d .
C56 C 0.0487(5) 0.5494(3) 0.5738(10) 0.032(2) Uani 1 1 d .
F57 F 0.0674(3) 0.59792(18) 0.5849(5) 0.0415(13) Uani 1 1 d .
O58 O 0.6120(3) 0.72621(18) 0.9163(5) 0.0569(13) Uani 1 1 d D
H58 H 0.648(3) 0.745(2) 0.938(7) 0.05 Uiso 1 1 d D
C59 C 0.6230(4) 0.6823(3) 0.9952(7) 0.0603(19) Uani 1 1 d .
H59A H 0.6603 0.6614 0.9712 0.09 Uiso 1 1 calc R
H59B H 0.5775 0.6634 0.9817 0.09 Uiso 1 1 calc R
H59C H 0.6387 0.6919 1.0872 0.09 Uiso 1 1 calc R
O60 O 0.4833(3) 0.77140(19) 0.7960(5) 0.0634(14) Uani 1 1 d .
H60 H 0.5146 0.7511 0.8353 0.095 Uiso 1 1 calc R
C61 C 0.5079(4) 0.8206(3) 0.8255(11) 0.075(3) Uani 1 1 d .
H61A H 0.4688 0.8443 0.7897 0.112 Uiso 1 1 calc R
H61B H 0.5493 0.8272 0.7871 0.112 Uiso 1 1 calc R
H61C H 0.5228 0.8247 0.9203 0.112 Uiso 1 1 calc R
O62 O 0.8426(3) 0.7248(2) 0.1539(6) 0.0574(16) Uani 1 1 d .
H62 H 0.8822 0.7281 0.2088 0.086 Uiso 1 1 calc R
C63 C 0.8524(5) 0.6927(4) 0.0510(8) 0.050(2) Uani 1 1 d .
H63A H 0.8079 0.6922 -0.0185 0.076 Uiso 1 1 calc R
H63B H 0.8633 0.6586 0.0848 0.076 Uiso 1 1 calc R
H63C H 0.8926 0.7051 0.016 0.076 Uiso 1 1 calc R
O64 O 0.7316(3) 0.7852(2) 0.0171(6) 0.0553(15) Uani 1 1 d .
H64 H 0.7667 0.7696 0.0635 0.083 Uiso 1 1 calc R
C65 C 0.7043(7) 0.8198(5) 0.0953(10) 0.075(3) Uani 1 1 d .
H65A H 0.6959 0.8026 0.1725 0.113 Uiso 1 1 calc R
H65B H 0.6585 0.8338 0.0451 0.113 Uiso 1 1 calc R
H65C H 0.7395 0.8468 0.1225 0.113 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 0 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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_3
C2 C1 C6 120.0(7) .
C2 C1 C42 118.9(7) .
C6 C1 C42 121.1(7) .
C1 C2 C3 120.9(7) .
C1 C2 H2 119.6 .
C3 C2 H2 119.6 .
C4 C3 C2 118.5(7) .
C4 C3 H3 120.7 .
C2 C3 H3 120.7 .
C3 C4 C5 123.2(7) .
C3 C4 H4 118.4 .
C5 C4 H4 118.4 .
C4 C5 C6 117.5(7) .
C4 C5 C7 120.4(7) .
C6 C5 C7 122.1(7) .
N43 C6 C5 121.8(7) .
N43 C6 C1 118.4(7) .
C5 C6 C1 119.8(7) .
N8 C7 C5 115.8(7) .
N8 C7 H7A 108.3 .
C5 C7 H7A 108.3 .
N8 C7 H7B 108.3 .
C5 C7 H7B 108.3 .
H7A C7 H7B 107.4 .
C9 N8 C13 111.0(7) .
C9 N8 C7 112.8(6) .
C13 N8 C7 111.1(6) .
C9 N8 I46 109.3(5) .
C13 N8 I46 110.3(5) .
C7 N8 I46 102.0(5) .
N8 C9 C10 111.2(7) .
N8 C9 H9A 109.4 .
C10 C9 H9A 109.4 .
N8 C9 H9B 109.4 .
C10 C9 H9B 109.4 .
H9A C9 H9B 108 .
N11 C10 C9 108.3(6) .
N11 C10 H10A 110 .
C9 C10 H10A 110 .
N11 C10 H10B 110 .
C9 C10 H10B 110 .
H10A C10 H10B 108.4 .
C12 N11 C10 108.4(5) .
C12 N11 C14 114.3(5) .
C10 N11 C14 111.8(5) .
N11 C12 C13 110.2(6) .
N11 C12 H12A 109.6 .
C13 C12 H12A 109.6 .
N11 C12 H12B 109.6 .
C13 C12 H12B 109.6 .
H12A C12 H12B 108.1 .
N8 C13 C12 110.5(6) .
N8 C13 H13A 109.5 .
C12 C13 H13A 109.5 .
N8 C13 H13B 109.5 .
C12 C13 H13B 109.5 .
H13A C13 H13B 108.1 .
N11 C14 C15 112.4(5) .
N11 C14 H14A 109.1 .
C15 C14 H14A 109.1 .
N11 C14 H14B 109.1 .
C15 C14 H14B 109.1 .
H14A C14 H14B 107.8 .
C16 C15 C20 119.4(5) .
C16 C15 C14 121.0(5) .
C20 C15 C14 119.6(5) .
C15 C16 C17 121.4(5) .
C15 C16 H16 119.3 .
C17 C16 H16 119.3 .
C18 C17 C16 118.6(5) .
C18 C17 H17 120.7 .
C16 C17 H17 120.7 .
C17 C18 C19 122.0(5) .
C17 C18 H18 119 .
C19 C18 H18 119 .
C18 C19 C20 119.3(5) .
C18 C19 C21 118.9(5) .
C20 C19 C21 121.5(5) .
N44 C20 C15 119.8(6) .
N44 C20 C19 121.0(6) .
C15 C20 C19 119.2(5) .
N22 C21 C19 114.3(5) .
N22 C21 H21A 108.7 .
C19 C21 H21A 108.7 .
N22 C21 H21B 108.7 .
C19 C21 H21B 108.7 .
H21A C21 H21B 107.6 .
C23 N22 C27 109.3(5) .
C23 N22 C21 112.8(5) .
C27 N22 C21 110.4(5) .
N22 C23 C24 110.8(5) .
N22 C23 H23A 109.5 .
C24 C23 H23A 109.5 .
N22 C23 H23B 109.5 .
C24 C23 H23B 109.5 .
H23A C23 H23B 108.1 .
N25 C24 C23 111.2(7) .
N25 C24 H24A 109.4 .
C23 C24 H24A 109.4 .
N25 C24 H24B 109.4 .
C23 C24 H24B 109.4 .
H24A C24 H24B 108 .
C26 N25 C24 110.4(6) .
C26 N25 C28 112.9(6) .
C24 N25 C28 111.9(6) .
N25 C26 C27 110.6(6) .
N25 C26 H26A 109.5 .
C27 C26 H26A 109.5 .
N25 C26 H26B 109.5 .
C27 C26 H26B 109.5 .
H26A C26 H26B 108.1 .
N22 C27 C26 108.8(6) .
N22 C27 H27A 109.9 .
C26 C27 H27A 109.9 .
N22 C27 H27B 109.9 .
C26 C27 H27B 109.9 .
H27A C27 H27B 108.3 .
N25 C28 C29 115.7(7) .
N25 C28 H28A 108.4 .
C29 C28 H28A 108.4 .
N25 C28 H28B 108.4 .
C29 C28 H28B 108.4 .
H28A C28 H28B 107.4 .
C30 C29 C34 120.4(7) .
C30 C29 C28 116.5(6) .
C34 C29 C28 123.1(7) .
C29 C30 C31 121.2(6) .
C29 C30 H30 119.4 .
C31 C30 H30 119.4 .
C32 C31 C30 117.5(7) .
C32 C31 H31 121.2 .
C30 C31 H31 121.2 .
C33 C32 C31 123.0(7) .
C33 C32 H32 118.5 .
C31 C32 H32 118.5 .
C32 C33 C34 119.9(7) .
C32 C33 C35 117.8(7) .
C34 C33 C35 122.0(7) .
N45 C34 C33 121.2(7) .
N45 C34 C29 121.0(7) .
C33 C34 C29 117.8(7) .
N36 C35 C33 114.3(6) .
N36 C35 H35A 108.7 .
C33 C35 H35A 108.7 .
N36 C35 H35B 108.7 .
C33 C35 H35B 108.7 .
H35A C35 H35B 107.6 .
C37 N36 C41 108.7(5) .
C37 N36 C35 109.6(5) .
C41 N36 C35 112.3(5) .
N36 C37 C38 111.4(6) .
N36 C37 H37A 109.3 .
C38 C37 H37A 109.3 .
N36 C37 H37B 109.3 .
C38 C37 H37B 109.3 .
H37A C37 H37B 108 .
N39 C38 C37 111.2(6) .
N39 C38 H38A 109.4 .
C37 C38 H38A 109.4 .
N39 C38 H38B 109.4 .
C37 C38 H38B 109.4 .
H38A C38 H38B 108 .
C42 N39 C38 110.2(5) .
C42 N39 C40 111.6(5) .
C38 N39 C40 108.4(5) .
N39 C40 C41 110.4(6) .
N39 C40 H40A 109.6 .
C41 C40 H40A 109.6 .
N39 C40 H40B 109.6 .
C41 C40 H40B 109.6 .
H40A C40 H40B 108.1 .
N36 C41 C40 110.1(7) .
N36 C41 H41A 109.6 .
C40 C41 H41A 109.6 .
N36 C41 H41B 109.6 .
C40 C41 H41B 109.6 .
H41A C41 H41B 108.2 .
N39 C42 C1 115.6(5) .
N39 C42 H42A 108.4 .
C1 C42 H42A 108.4 .
N39 C42 H42B 108.4 .
C1 C42 H42B 108.4 .
H42A C42 H42B 107.4 .
C6 N43 H43A 118(5) .
C6 N43 H43B 119(5) .
H43A N43 H43B 119(7) .
C20 N44 H44A 114(6) .
C20 N44 H44B 122(6) .
H44A N44 H44B 121(5) .
C34 N45 H45A 134(6) .
C34 N45 H45B 121(5) .
H45A N45 H45B 101(7) .
C47 I46 N8 179.1(3) .
C48 C47 C56 115.4(8) .
C48 C47 I46 122.6(7) .
C56 C47 I46 122.0(6) .
F49 C48 C47 119.3(9) .
F49 C48 C50 117.4(8) .
C47 C48 C50 123.3(8) .
F51 C50 C52 121.6(9) .
F51 C50 C48 118.3(8) .
C52 C50 C48 120.1(8) .
C50 C52 C54 119.6(8) .
C50 C52 I53 121.3(6) .
C54 C52 I53 119.1(6) .
C52 I53 N25 177.6(3) 2_465
F55 C54 C52 122.0(8) .
F55 C54 C56 118.8(8) .
C52 C54 C56 119.1(8) .
F57 C56 C54 118.1(8) .
F57 C56 C47 119.3(9) .
C54 C56 C47 122.5(8) .
C59 O58 H58 110(5) .
O58 C59 H59A 109.5 .
O58 C59 H59B 109.5 .
H59A C59 H59B 109.5 .
O58 C59 H59C 109.5 .
H59A C59 H59C 109.5 .
H59B C59 H59C 109.5 .
C61 O60 H60 109.5 .
O60 C61 H61A 109.5 .
O60 C61 H61B 109.5 .
H61A C61 H61B 109.5 .
O60 C61 H61C 109.5 .
H61A C61 H61C 109.5 .
H61B C61 H61C 109.5 .
C63 O62 H62 109.5 .
O62 C63 H63A 109.5 .
O62 C63 H63B 109.5 .
H63A C63 H63B 109.5 .
O62 C63 H63C 109.5 .
H63A C63 H63C 109.5 .
H63B C63 H63C 109.5 .
C65 O64 H64 109.5 .
O64 C65 H65A 109.5 .
O64 C65 H65B 109.5 .
H65A C65 H65B 109.5 .
O64 C65 H65C 109.5 .
H65A C65 H65C 109.5 .
H65B C65 H65C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.372(10) .
C1 C6 1.415(11) .
C1 C42 1.511(10) .
C2 C3 1.395(11) .
C2 H2 0.95 .
C3 C4 1.369(12) .
C3 H3 0.95 .
C4 C5 1.395(10) .
C4 H4 0.95 .
C5 C6 1.406(11) .
C5 C7 1.491(12) .
C6 N43 1.382(9) .
C7 N8 1.490(10) .
C7 H7A 0.99 .
C7 H7B 0.99 .
N8 C9 1.463(11) .
N8 C13 1.489(9) .
N8 I46 2.758(7) .
C9 C10 1.516(10) .
C9 H9A 0.99 .
C9 H9B 0.99 .
C10 N11 1.457(7) .
C10 H10A 0.99 .
C10 H10B 0.99 .
N11 C12 1.455(8) .
N11 C14 1.477(8) .
C12 C13 1.494(11) .
C12 H12A 0.99 .
C12 H12B 0.99 .
C13 H13A 0.99 .
C13 H13B 0.99 .
C14 C15 1.504(8) .
C14 H14A 0.99 .
C14 H14B 0.99 .
C15 C16 1.384(8) .
C15 C20 1.412(7) .
C16 C17 1.399(8) .
C16 H16 0.95 .
C17 C18 1.379(8) .
C17 H17 0.95 .
C18 C19 1.382(8) .
C18 H18 0.95 .
C19 C20 1.417(7) .
C19 C21 1.523(7) .
C20 N44 1.368(7) .
C21 N22 1.468(7) .
C21 H21A 0.99 .
C21 H21B 0.99 .
N22 C23 1.446(7) .
N22 C27 1.454(8) .
C23 C24 1.508(10) .
C23 H23A 0.99 .
C23 H23B 0.99 .
C24 N25 1.474(11) .
C24 H24A 0.99 .
C24 H24B 0.99 .
N25 C26 1.467(9) .
N25 C28 1.479(9) .
C26 C27 1.536(10) .
C26 H26A 0.99 .
C26 H26B 0.99 .
C27 H27A 0.99 .
C27 H27B 0.99 .
C28 C29 1.540(11) .
C28 H28A 0.99 .
C28 H28B 0.99 .
C29 C30 1.374(10) .
C29 C34 1.418(11) .
C30 C31 1.406(10) .
C30 H30 0.95 .
C31 C32 1.377(10) .
C31 H31 0.95 .
C32 C33 1.368(11) .
C32 H32 0.95 .
C33 C34 1.407(11) .
C33 C35 1.522(10) .
C34 N45 1.368(9) .
C35 N36 1.477(8) .
C35 H35A 0.99 .
C35 H35B 0.99 .
N36 C37 1.467(8) .
N36 C41 1.473(9) .
C37 C38 1.492(11) .
C37 H37A 0.99 .
C37 H37B 0.99 .
C38 N39 1.466(8) .
C38 H38A 0.99 .
C38 H38B 0.99 .
N39 C42 1.463(8) .
N39 C40 1.471(9) .
C40 C41 1.493(9) .
C40 H40A 0.99 .
C40 H40B 0.99 .
C41 H41A 0.99 .
C41 H41B 0.99 .
C42 H42A 0.99 .
C42 H42B 0.99 .
N43 H43A 0.873(16) .
N43 H43B 0.86(2) .
N44 H44A 0.86(2) .
N44 H44B 0.86(2) .
N45 H45A 0.86(2) .
N45 H45B 0.86(2) .
I46 C47 2.103(8) .
C47 C48 1.370(12) .
C47 C56 1.401(13) .
C48 F49 1.370(10) .
C48 C50 1.386(14) .
C50 F51 1.344(10) .
C50 C52 1.357(13) .
C52 C54 1.388(11) .
C52 I53 2.125(8) .
I53 N25 2.770(7) 2_465
C54 F55 1.317(10) .
C54 C56 1.389(13) .
C56 F57 1.341(10) .
O58 C59 1.423(8) .
O58 H58 0.84(2) .
C59 H59A 0.98 .
C59 H59B 0.98 .
C59 H59C 0.98 .
O60 C61 1.404(8) .
O60 H60 0.84 .
C61 H61A 0.98 .
C61 H61B 0.98 .
C61 H61C 0.98 .
O62 C63 1.430(10) .
O62 H62 0.84 .
C63 H63A 0.98 .
C63 H63B 0.98 .
C63 H63C 0.98 .
O64 C65 1.413(12) .
O64 H64 0.84 .
C65 H65A 0.98 .
C65 H65B 0.98 .
C65 H65C 0.98 .
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
N43 H43A N39 0.873(16) 2.21(5) 2.882(9) 134(6) .
N43 H43B O64 0.86(2) 2.45(4) 3.204(10) 147(6) 4_465
N44 H44A N22 0.86(2) 2.14(6) 2.843(12) 138(8) .
N44 H44B N11 0.86(2) 2.28(7) 2.880(12) 127(7) .
N45 H45B N36 0.86(2) 2.30(6) 2.881(9) 125(6) .
N45 H45A O62 0.86(2) 2.59(3) 3.440(10) 175(8) .
O58 H58 O64 0.84(2) 1.93(3) 2.764(8) 170(7) 1_556
O60 H60 O58 0.84 1.96 2.754(7) 157 .
O62 H62 O60 0.84 1.92 2.742(8) 164.2 4_564
O64 H64 O62 0.84 1.94 2.774(7) 171.4 .
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
C6 C1 C2 C3 2.8(11)
C42 C1 C2 C3 -175.3(6)
C1 C2 C3 C4 -2.3(11)
C2 C3 C4 C5 -0.8(11)
C3 C4 C5 C6 3.2(11)
C3 C4 C5 C7 -175.6(7)
C4 C5 C6 N43 174.2(7)
C7 C5 C6 N43 -7.1(11)
C4 C5 C6 C1 -2.5(10)
C7 C5 C6 C1 176.2(7)
C2 C1 C6 N43 -177.2(7)
C42 C1 C6 N43 1.0(10)
C2 C1 C6 C5 -0.3(10)
C42 C1 C6 C5 177.8(6)
C4 C5 C7 N8 85.1(9)
C6 C5 C7 N8 -93.7(8)
C5 C7 N8 C9 -58.0(9)
C5 C7 N8 C13 67.4(9)
C5 C7 N8 I46 -175.1(5)
C13 N8 C9 C10 53.9(9)
C7 N8 C9 C10 179.4(6)
I46 N8 C9 C10 -67.9(7)
N8 C9 C10 N11 -59.5(9)
C9 C10 N11 C12 63.6(7)
C9 C10 N11 C14 -169.5(6)
C10 N11 C12 C13 -63.8(7)
C14 N11 C12 C13 170.7(6)
C9 N8 C13 C12 -52.7(9)
C7 N8 C13 C12 -179.1(7)
I46 N8 C13 C12 68.6(7)
N11 C12 C13 N8 57.8(8)
C12 N11 C14 C15 -157.3(5)
C10 N11 C14 C15 79.1(6)
N11 C14 C15 C16 -123.5(6)
N11 C14 C15 C20 58.6(7)
C20 C15 C16 C17 1.9(8)
C14 C15 C16 C17 -176.0(5)
C15 C16 C17 C18 0.8(9)
C16 C17 C18 C19 -2.1(9)
C17 C18 C19 C20 0.7(8)
C17 C18 C19 C21 -173.2(5)
C16 C15 C20 N44 177.4(6)
C14 C15 C20 N44 -4.7(8)
C16 C15 C20 C19 -3.3(7)
C14 C15 C20 C19 174.6(5)
C18 C19 C20 N44 -178.6(6)
C21 C19 C20 N44 -4.9(9)
C18 C19 C20 C15 2.1(7)
C21 C19 C20 C15 175.8(5)
C18 C19 C21 N22 -139.0(5)
C20 C19 C21 N22 47.2(7)
C19 C21 N22 C23 73.6(6)
C19 C21 N22 C27 -163.8(5)
C27 N22 C23 C24 61.1(8)
C21 N22 C23 C24 -175.7(6)
N22 C23 C24 N25 -56.9(9)
C23 C24 N25 C26 53.9(9)
C23 C24 N25 C28 -179.5(6)
C24 N25 C26 C27 -55.3(8)
C28 N25 C26 C27 178.6(6)
C23 N22 C27 C26 -61.7(7)
C21 N22 C27 C26 173.7(5)
N25 C26 C27 N22 59.5(8)
C26 N25 C28 C29 70.8(8)
C24 N25 C28 C29 -54.5(9)
N25 C28 C29 C30 92.1(8)
N25 C28 C29 C34 -87.7(9)
C34 C29 C30 C31 3.3(11)
C28 C29 C30 C31 -176.4(7)
C29 C30 C31 C32 -0.7(11)
C30 C31 C32 C33 -0.2(11)
C31 C32 C33 C34 -1.5(11)
C31 C32 C33 C35 -175.2(6)
C32 C33 C34 N45 -178.2(7)
C35 C33 C34 N45 -4.8(11)
C32 C33 C34 C29 4.0(11)
C35 C33 C34 C29 177.5(6)
C30 C29 C34 N45 177.3(7)
C28 C29 C34 N45 -2.9(11)
C30 C29 C34 C33 -5.0(11)
C28 C29 C34 C33 174.8(7)
C32 C33 C35 N36 -137.4(7)
C34 C33 C35 N36 49.1(9)
C33 C35 N36 C37 177.1(6)
C33 C35 N36 C41 56.2(8)
C41 N36 C37 C38 -57.0(8)
C35 N36 C37 C38 179.9(6)
N36 C37 C38 N39 57.7(8)
C37 C38 N39 C42 -179.8(6)
C37 C38 N39 C40 -57.4(8)
C42 N39 C40 C41 -179.1(5)
C38 N39 C40 C41 59.4(8)
C37 N36 C41 C40 58.6(7)
C35 N36 C41 C40 -180.0(5)
N39 C40 C41 N36 -61.1(6)
C38 N39 C42 C1 177.1(6)
C40 N39 C42 C1 56.6(8)
C2 C1 C42 N39 -130.5(7)
C6 C1 C42 N39 51.3(9)
C56 C47 C48 F49 -179.0(8)
I46 C47 C48 F49 -0.2(12)
C56 C47 C48 C50 1.7(12)
I46 C47 C48 C50 -179.4(7)
F49 C48 C50 F51 -0.1(13)
C47 C48 C50 F51 179.2(8)
F49 C48 C50 C52 179.2(8)
C47 C48 C50 C52 -1.5(14)
F51 C50 C52 C54 179.4(8)
C48 C50 C52 C54 0.2(12)
F51 C50 C52 I53 -1.7(12)
C48 C50 C52 I53 179.1(7)
C50 C52 C54 F55 179.5(8)
I53 C52 C54 F55 0.6(10)
C50 C52 C54 C56 0.8(10)
I53 C52 C54 C56 -178.1(6)
F55 C54 C56 F57 0.9(12)
C52 C54 C56 F57 179.6(8)
F55 C54 C56 C47 -179.3(8)
C52 C54 C56 C47 -0.5(13)
C48 C47 C56 F57 179.1(8)
I46 C47 C56 F57 0.3(12)
C48 C47 C56 C54 -0.7(13)
I46 C47 C56 C54 -179.5(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139144776
