#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/18/4501821.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_4501821
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_compound_source        'synthesis as described'
_chemical_formula_moiety         'C36 H54 N9, 6(C6 F4 I2), 3(C2 H6 O), 3(Cl)'
_chemical_formula_sum            'C78 H72 Cl3 F24 I12 N9 O3'
_chemical_formula_weight         3268.6
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-03-08T13:12:18-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 91.9240(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.0024(2)
_cell_length_b                   28.0603(4)
_cell_length_c                   23.8472(3)
_cell_measurement_reflns_used    22683
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407
_cell_measurement_wavelength     0.71073
_cell_volume                     10033.3(2)
_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)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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      0.495344E-1
_diffrn_orient_matrix_UB_12      -0.10737E-2
_diffrn_orient_matrix_UB_13      -0.270044E-1
_diffrn_orient_matrix_UB_21      -0.158337E-1
_diffrn_orient_matrix_UB_22      0.328664E-1
_diffrn_orient_matrix_UB_23      -0.131299E-1
_diffrn_orient_matrix_UB_31      0.417573E-1
_diffrn_orient_matrix_UB_32      0.137362E-1
_diffrn_orient_matrix_UB_33      0.29305E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            70361
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         1.63
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    3.877
_exptl_absorpt_correction_T_max  0.4313
_exptl_absorpt_correction_T_min  0.3326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.164
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             6120
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         4.325
_refine_diff_density_min         -3.291
_refine_diff_density_rms         0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1168
_refine_ls_number_reflns         22959
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0589
_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)+(0.0643P)²+122.4400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1442
_refine_ls_wR_factor_ref         0.163
_reflns_number_gt                16885
_reflns_number_total             22959
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg100516t_si_001.cif
_cod_data_source_block           1-HCl-F4DIB
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4501821
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.8559(5) 0.2441(3) 0.2668(3) 0.0230(16) Uani 1 1 d .
C2 C 0.9002(6) 0.2017(3) 0.2719(3) 0.0307(19) Uani 1 1 d .
H2 H 0.9099 0.1834 0.2391 0.037 Uiso 1 1 calc R
C3 C 0.9313(5) 0.1844(3) 0.3231(3) 0.0289(18) Uani 1 1 d .
H3 H 0.9591 0.154 0.326 0.035 Uiso 1 1 calc R
C4 C 0.9211(5) 0.2125(3) 0.3702(3) 0.0252(17) Uani 1 1 d .
H4 H 0.9459 0.2019 0.4052 0.03 Uiso 1 1 calc R
C5 C 0.8756(5) 0.2558(3) 0.3679(3) 0.0223(16) Uani 1 1 d .
C6 C 0.8411(5) 0.2721(3) 0.3157(3) 0.0221(16) Uani 1 1 d .
C7 C 0.8668(5) 0.2845(3) 0.4205(3) 0.0228(16) Uani 1 1 d D
H7A H 0.8379 0.3153 0.4108 0.027 Uiso 1 1 calc R
H7B H 0.9272 0.2916 0.4365 0.027 Uiso 1 1 calc R
N8 N 0.8133(4) 0.2599(2) 0.4647(3) 0.0203(13) Uani 1 1 d .
H8 H 0.848(3) 0.2352(13) 0.4787(17) 0.024 Uiso 1 1 d D
C9 C 0.7969(5) 0.2948(3) 0.5111(3) 0.0239(16) Uani 1 1 d D
H9A H 0.7655 0.3231 0.4953 0.029 Uiso 1 1 calc R
H9B H 0.8547 0.3055 0.5278 0.029 Uiso 1 1 calc R
C10 C 0.7412(5) 0.2726(3) 0.5564(3) 0.0250(17) Uani 1 1 d .
H10A H 0.7743 0.2458 0.5742 0.03 Uiso 1 1 calc R
H10B H 0.7299 0.2967 0.5858 0.03 Uiso 1 1 calc R
N11 N 0.6558(4) 0.2553(2) 0.5324(3) 0.0225(14) Uani 1 1 d .
C12 C 0.6741(5) 0.2186(3) 0.4908(3) 0.0235(16) Uani 1 1 d .
H12A H 0.6172 0.2051 0.4758 0.028 Uiso 1 1 calc R
H12B H 0.7089 0.1925 0.5089 0.028 Uiso 1 1 calc R
C13 C 0.7259(5) 0.2395(3) 0.4434(3) 0.0229(16) Uani 1 1 d D
H13A H 0.7372 0.2143 0.4154 0.027 Uiso 1 1 calc R
H13B H 0.6901 0.2649 0.4246 0.027 Uiso 1 1 calc R
C14 C 0.6040(5) 0.2365(3) 0.5790(3) 0.0251(17) Uani 1 1 d .
H14A H 0.5941 0.2626 0.606 0.03 Uiso 1 1 calc R
H14B H 0.6397 0.2116 0.5988 0.03 Uiso 1 1 calc R
C15 C 0.5146(5) 0.2156(3) 0.5611(3) 0.0223(16) Uani 1 1 d .
C16 C 0.4919(5) 0.1707(3) 0.5818(3) 0.0256(17) Uani 1 1 d .
H16 H 0.5351 0.1533 0.6034 0.031 Uiso 1 1 calc R
C17 C 0.4081(6) 0.1508(3) 0.5718(3) 0.0290(18) Uani 1 1 d .
H17 H 0.3944 0.12 0.5855 0.035 Uiso 1 1 calc R
C18 C 0.3454(5) 0.1769(3) 0.5415(3) 0.0247(16) Uani 1 1 d .
H18 H 0.2874 0.1639 0.5353 0.03 Uiso 1 1 calc R
C19 C 0.3646(5) 0.2217(3) 0.5198(3) 0.0219(15) Uani 1 1 d .
C20 C 0.4514(5) 0.2417(3) 0.5283(3) 0.0240(16) Uani 1 1 d .
C21 C 0.2922(5) 0.2484(3) 0.4883(3) 0.0239(16) Uani 1 1 d .
H21A H 0.3157 0.2798 0.477 0.029 Uiso 1 1 calc R
H21B H 0.2425 0.2543 0.5138 0.029 Uiso 1 1 calc R
N22 N 0.2561(4) 0.2227(2) 0.4367(2) 0.0204(13) Uani 1 1 d D
H22 H 0.2281 0.195 0.4482 0.025 Uiso 1 1 calc RD
C23 C 0.1872(5) 0.2538(3) 0.4075(3) 0.0259(17) Uani 1 1 d .
H23A H 0.2139 0.285 0.3982 0.031 Uiso 1 1 calc R
H23B H 0.1371 0.2595 0.4326 0.031 Uiso 1 1 calc R
C24 C 0.1532(5) 0.2294(3) 0.3542(3) 0.0260(17) Uani 1 1 d .
H24A H 0.1244 0.1988 0.3636 0.031 Uiso 1 1 calc R
H24B H 0.1081 0.2498 0.3347 0.031 Uiso 1 1 calc R
N25 N 0.2277(4) 0.2206(3) 0.3173(3) 0.0250(14) Uani 1 1 d .
C26 C 0.2895(5) 0.1864(3) 0.3455(3) 0.0216(15) Uani 1 1 d .
H26A H 0.3378 0.1779 0.3201 0.026 Uiso 1 1 calc R
H26B H 0.2571 0.157 0.3551 0.026 Uiso 1 1 calc R
C27 C 0.3280(5) 0.2090(3) 0.3976(3) 0.0249(17) Uani 1 1 d .
H27A H 0.3623 0.2377 0.3875 0.03 Uiso 1 1 calc R
H27B H 0.3695 0.1864 0.4167 0.03 Uiso 1 1 calc R
C28 C 0.1969(5) 0.2032(3) 0.2621(3) 0.0262(17) Uani 1 1 d .
H28A H 0.1524 0.2259 0.2459 0.031 Uiso 1 1 calc R
H28B H 0.1668 0.1721 0.2666 0.031 Uiso 1 1 calc R
C29 C 0.2723(5) 0.1975(3) 0.2214(3) 0.0233(16) Uani 1 1 d .
C30 C 0.2805(6) 0.1541(3) 0.1942(3) 0.0273(18) Uani 1 1 d .
H30 H 0.2411 0.1288 0.2028 0.033 Uiso 1 1 calc R
C31 C 0.3438(5) 0.1468(3) 0.1553(3) 0.0282(18) Uani 1 1 d .
H31 H 0.3489 0.1168 0.1371 0.034 Uiso 1 1 calc R
C32 C 0.3998(5) 0.1838(3) 0.1429(3) 0.0261(17) Uani 1 1 d .
H32 H 0.4431 0.1793 0.1152 0.031 Uiso 1 1 calc R
C33 C 0.3949(5) 0.2279(3) 0.1701(3) 0.0223(16) Uani 1 1 d .
C34 C 0.3322(5) 0.2343(3) 0.2119(3) 0.0216(16) Uani 1 1 d .
C35 C 0.4556(5) 0.2675(3) 0.1523(3) 0.0242(16) Uani 1 1 d .
H35A H 0.4466 0.2954 0.1768 0.029 Uiso 1 1 calc R
H35B H 0.4383 0.277 0.1134 0.029 Uiso 1 1 calc R
N36 N 0.5536(4) 0.2546(2) 0.1545(3) 0.0196(13) Uani 1 1 d D
H36 H 0.565(6) 0.234(2) 0.126(3) 0.023 Uiso 1 1 d D
C37 C 0.6082(5) 0.2976(3) 0.1408(3) 0.0211(15) Uani 1 1 d .
H37A H 0.5936 0.324 0.1665 0.025 Uiso 1 1 calc R
H37B H 0.5932 0.308 0.1019 0.025 Uiso 1 1 calc R
C38 C 0.7071(5) 0.2865(3) 0.1463(3) 0.0239(16) Uani 1 1 d .
H38A H 0.7227 0.262 0.1185 0.029 Uiso 1 1 calc R
H38B H 0.7419 0.3157 0.1387 0.029 Uiso 1 1 calc R
N39 N 0.7299(4) 0.2692(2) 0.2031(3) 0.0223(14) Uani 1 1 d .
C40 C 0.6819(5) 0.2244(3) 0.2119(3) 0.0272(17) Uani 1 1 d .
H40A H 0.6999 0.2108 0.2489 0.033 Uiso 1 1 calc R
H40B H 0.6973 0.2011 0.1826 0.033 Uiso 1 1 calc R
C41 C 0.5821(5) 0.2332(3) 0.2095(3) 0.0228(16) Uani 1 1 d .
H41A H 0.5502 0.2028 0.2149 0.027 Uiso 1 1 calc R
H41B H 0.5663 0.2551 0.2403 0.027 Uiso 1 1 calc R
C42 C 0.8275(5) 0.2634(3) 0.2097(3) 0.0272(17) Uani 1 1 d .
H42A H 0.8565 0.2947 0.2041 0.033 Uiso 1 1 calc R
H42B H 0.8482 0.2414 0.1804 0.033 Uiso 1 1 calc R
N43 N 0.7968(5) 0.3150(3) 0.3092(3) 0.0311(16) Uani 1 1 d .
H43A H 0.7675 0.3214 0.3412 0.047 Uiso 1 1 d R
H43B H 0.7566 0.3127 0.2799 0.047 Uiso 1 1 d R
N44 N 0.4733(5) 0.2857(2) 0.5084(3) 0.0302(16) Uani 1 1 d .
H44B H 0.4472 0.2897 0.4737 0.045 Uiso 1 1 d R
H44C H 0.5336 0.2875 0.5059 0.045 Uiso 1 1 d R
N45 N 0.3259(5) 0.2772(3) 0.2414(3) 0.0281(15) Uani 1 1 d .
H45B H 0.3816 0.2887 0.2495 0.042 Uiso 1 1 d R
H45C H 0.2972 0.272 0.2738 0.042 Uiso 1 1 d R
I46 I 0.45729(6) -0.14483(3) 0.15080(4) 0.0608(2) Uani 1 1 d .
C47 C 0.4763(7) -0.0768(4) 0.1197(5) 0.048(3) Uani 1 1 d .
C48 C 0.5546(7) -0.0636(4) 0.0978(5) 0.051(3) Uani 1 1 d .
F49 F 0.6217(5) -0.0950(3) 0.0955(4) 0.080(2) Uani 1 1 d .
C50 C 0.5685(7) -0.0175(4) 0.0776(5) 0.054(3) Uani 1 1 d .
F51 F 0.6462(5) -0.0070(3) 0.0551(4) 0.080(2) Uani 1 1 d .
C52 C 0.5009(7) 0.0153(4) 0.0779(5) 0.047(3) Uani 1 1 d .
I53 I 0.52246(5) 0.08617(3) 0.05307(3) 0.04849(18) Uani 1 1 d .
C54 C 0.4211(7) 0.0022(4) 0.0988(7) 0.062(4) Uani 1 1 d .
F55 F 0.3545(5) 0.0330(3) 0.1017(5) 0.104(4) Uani 1 1 d .
C56 C 0.4088(8) -0.0427(4) 0.1205(7) 0.065(4) Uani 1 1 d .
F57 F 0.3294(6) -0.0534(3) 0.1412(6) 0.115(4) Uani 1 1 d .
I58 I 0.52388(5) -0.06898(2) 0.29322(3) 0.04769(17) Uani 1 1 d .
C59 C 0.5348(6) 0.0035(3) 0.3108(4) 0.034(2) Uani 1 1 d .
C60 C 0.5036(7) 0.0360(4) 0.2720(4) 0.044(2) Uani 1 1 d .
F61 F 0.4659(6) 0.0224(3) 0.2238(3) 0.079(3) Uani 1 1 d .
C62 C 0.5128(7) 0.0848(4) 0.2818(4) 0.041(2) Uani 1 1 d .
F63 F 0.4826(6) 0.1152(2) 0.2435(3) 0.071(2) Uani 1 1 d .
C64 C 0.5514(6) 0.1019(3) 0.3318(4) 0.0310(19) Uani 1 1 d .
I65 I 0.55765(4) 0.17485(2) 0.34686(2) 0.02933(13) Uani 1 1 d .
C66 C 0.5833(6) 0.0679(3) 0.3705(4) 0.0333(19) Uani 1 1 d .
F67 F 0.6227(5) 0.0828(2) 0.4178(2) 0.0540(17) Uani 1 1 d .
C68 C 0.5743(6) 0.0201(4) 0.3596(4) 0.035(2) Uani 1 1 d .
F69 F 0.6044(5) -0.0108(2) 0.3993(3) 0.0545(16) Uani 1 1 d .
I70 I 0.24581(4) 0.36710(2) 0.19443(3) 0.03565(14) Uani 1 1 d .
C71 C 0.2121(6) 0.4309(3) 0.1531(4) 0.0321(19) Uani 1 1 d .
C72 C 0.1859(6) 0.4307(3) 0.0966(4) 0.0318(19) Uani 1 1 d .
F73 F 0.1818(4) 0.38892(19) 0.0686(2) 0.0434(13) Uani 1 1 d .
C74 C 0.1632(6) 0.4717(3) 0.0687(4) 0.033(2) Uani 1 1 d .
F75 F 0.1377(5) 0.4683(2) 0.0148(2) 0.0509(16) Uani 1 1 d .
C76 C 0.1657(6) 0.5153(3) 0.0956(4) 0.0321(19) Uani 1 1 d .
I77 I 0.13253(4) 0.57635(2) 0.04994(3) 0.03735(14) Uani 1 1 d .
C78 C 0.1930(6) 0.5161(3) 0.1514(4) 0.0330(19) Uani 1 1 d .
F79 F 0.1965(4) 0.5575(2) 0.1795(2) 0.0467(14) Uani 1 1 d .
C80 C 0.2154(7) 0.4748(4) 0.1798(4) 0.036(2) Uani 1 1 d .
F81 F 0.2417(5) 0.4775(2) 0.2342(2) 0.0549(17) Uani 1 1 d .
I82 I 0.66347(4) 0.42116(2) 0.08024(2) 0.02736(12) Uani 1 1 d .
C83 C 0.6976(6) 0.4632(3) 0.1499(4) 0.0301(18) Uani 1 1 d .
C84 C 0.6941(6) 0.5126(3) 0.1479(4) 0.034(2) Uani 1 1 d .
F85 F 0.6651(4) 0.5338(2) 0.1004(2) 0.0498(15) Uani 1 1 d .
C86 C 0.7170(7) 0.5407(3) 0.1932(4) 0.040(2) Uani 1 1 d .
F87 F 0.7113(5) 0.5879(2) 0.1879(3) 0.0578(17) Uani 1 1 d .
C88 C 0.7447(6) 0.5203(4) 0.2426(4) 0.044(2) Uani 1 1 d .
I89 I 0.78073(6) 0.56237(3) 0.31228(3) 0.0641(2) Uani 1 1 d .
C90 C 0.7490(7) 0.4712(4) 0.2463(4) 0.038(2) Uani 1 1 d .
F91 F 0.7759(4) 0.4494(3) 0.2940(2) 0.0551(16) Uani 1 1 d .
C92 C 0.7259(6) 0.4431(3) 0.2006(4) 0.0294(18) Uani 1 1 d .
F93 F 0.7336(4) 0.39561(19) 0.2051(2) 0.0387(12) Uani 1 1 d .
I94 I 0.52689(4) 0.38030(2) 0.27861(2) 0.02957(13) Uani 1 1 d .
C95 C 0.4988(5) 0.4394(3) 0.2272(4) 0.0278(17) Uani 1 1 d .
C96 C 0.4645(5) 0.4327(3) 0.1729(3) 0.0226(16) Uani 1 1 d .
F97 F 0.4558(3) 0.38861(17) 0.15204(19) 0.0305(11) Uani 1 1 d .
C98 C 0.4406(5) 0.4710(3) 0.1394(3) 0.0263(17) Uani 1 1 d .
F99 F 0.4077(4) 0.46199(18) 0.0873(2) 0.0331(11) Uani 1 1 d .
C100 C 0.4510(5) 0.5171(3) 0.1579(3) 0.0258(17) Uani 1 1 d .
I101 I 0.41826(4) 0.574147(19) 0.10396(2) 0.02729(12) Uani 1 1 d .
C102 C 0.4856(6) 0.5244(3) 0.2117(3) 0.0297(18) Uani 1 1 d .
F103 F 0.4997(4) 0.56807(18) 0.2317(2) 0.0414(13) Uani 1 1 d .
C104 C 0.5102(6) 0.4863(3) 0.2453(3) 0.0298(18) Uani 1 1 d .
F105 F 0.5454(4) 0.4942(2) 0.2971(2) 0.0411(13) Uani 1 1 d .
I106 I 0.74446(4) 0.64306(2) 0.43544(3) 0.04028(15) Uani 1 1 d .
C107 C 0.6217(6) 0.6106(4) 0.4155(4) 0.036(2) Uani 1 1 d .
C108 C 0.6057(6) 0.5629(3) 0.4292(4) 0.035(2) Uani 1 1 d .
F109 F 0.6684(4) 0.5375(2) 0.4579(3) 0.0505(16) Uani 1 1 d .
C110 C 0.5274(6) 0.5418(3) 0.4131(4) 0.037(2) Uani 1 1 d .
F111 F 0.5142(4) 0.4956(2) 0.4287(3) 0.0522(16) Uani 1 1 d .
C112 C 0.4620(6) 0.5656(3) 0.3831(4) 0.039(2) Uani 1 1 d .
I113 I 0.34542(5) 0.53201(3) 0.35661(4) 0.0555(2) Uani 1 1 d .
C114 C 0.4782(7) 0.6124(4) 0.3697(4) 0.040(2) Uani 1 1 d .
F115 F 0.4172(4) 0.6378(2) 0.3404(3) 0.0589(18) Uani 1 1 d .
C116 C 0.5565(7) 0.6344(4) 0.3857(4) 0.038(2) Uani 1 1 d .
F117 F 0.5676(4) 0.6799(2) 0.3709(2) 0.0476(15) Uani 1 1 d .
Cl1 Cl 0.54271(15) 0.28904(8) 0.35364(9) 0.0352(5) Uani 1 1 d .
Cl2 Cl 0.57170(14) 0.19973(8) 0.03978(8) 0.0300(4) Uani 1 1 d .
Cl3 Cl 0.11314(12) 0.15667(7) 0.48459(8) 0.0253(4) Uani 1 1 d .
O1A O 0.9226(4) 0.1922(2) 0.5169(2) 0.0258(12) Uani 1 1 d U
H1A H 0.9664 0.1905 0.496 0.039 Uiso 1 1 calc R
C2A C 0.8931(6) 0.1448(3) 0.5305(3) 0.0276(17) Uani 1 1 d U
H2A1 H 0.8471 0.1469 0.5592 0.033 Uiso 1 1 calc R
H2A2 H 0.9441 0.1265 0.5468 0.033 Uiso 1 1 calc R
C3A C 0.8550(7) 0.1185(3) 0.4803(4) 0.037(2) Uani 1 1 d U
H3A1 H 0.8357 0.0867 0.4917 0.056 Uiso 1 1 calc R
H3A2 H 0.9007 0.1156 0.4521 0.056 Uiso 1 1 calc R
H3A3 H 0.8038 0.1362 0.4643 0.056 Uiso 1 1 calc R
O1B O 0.6911(4) 0.3591(2) 0.4064(3) 0.0392(15) Uani 1 1 d U
H1B H 0.6448 0.3435 0.398 0.059 Uiso 1 1 calc R
C2B C 0.6667(7) 0.4058(4) 0.4254(4) 0.044(2) Uani 1 1 d DU
H2B1 H 0.6174 0.4181 0.4008 0.053 Uiso 1 1 calc R
H2B2 H 0.7183 0.4275 0.4216 0.053 Uiso 1 1 calc R
C3B C 0.6384(15) 0.4069(6) 0.4843(5) 0.118(8) Uani 1 1 d DU
H3B1 H 0.6234 0.4397 0.4947 0.177 Uiso 1 1 calc R
H3B2 H 0.6872 0.3953 0.5091 0.177 Uiso 1 1 calc R
H3B3 H 0.586 0.3865 0.4882 0.177 Uiso 1 1 calc R
O1C O 0.3645(7) 0.3267(4) 0.3971(6) 0.107(4) Uani 1 1 d U
H1C H 0.4094 0.3235 0.3773 0.161 Uiso 1 1 calc R
C2C C 0.3310(9) 0.3742(5) 0.3916(7) 0.075(4) Uani 1 1 d DU
H2C1 H 0.2699 0.3769 0.4058 0.09 Uiso 1 1 calc R
H2C2 H 0.3309 0.3851 0.3521 0.09 Uiso 1 1 calc R
C3C C 0.3947(12) 0.4005(7) 0.4264(7) 0.102(5) Uani 1 1 d DU
H3C1 H 0.3786 0.4343 0.4263 0.154 Uiso 1 1 calc R
H3C2 H 0.4545 0.3967 0.4115 0.154 Uiso 1 1 calc R
H3C3 H 0.3944 0.3882 0.4648 0.154 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'
O O 0.0106 0.006 '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'
Cl Cl 0.1484 0.1585 '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'
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 119.6(7) .
C2 C1 C42 120.9(7) .
C6 C1 C42 119.4(7) .
C1 C2 C3 122.2(8) .
C1 C2 H2 118.9 .
C3 C2 H2 118.9 .
C2 C3 C4 118.4(8) .
C2 C3 H3 120.8 .
C4 C3 H3 120.8 .
C3 C4 C5 122.1(7) .
C3 C4 H4 118.9 .
C5 C4 H4 118.9 .
C4 C5 C6 118.8(7) .
C4 C5 C7 119.5(7) .
C6 C5 C7 121.6(7) .
N43 C6 C5 122.8(7) .
N43 C6 C1 118.4(7) .
C5 C6 C1 118.8(7) .
C5 C7 N8 113.5(6) .
C5 C7 H7A 108.9 .
N8 C7 H7A 108.9 .
C5 C7 H7B 108.9 .
N8 C7 H7B 108.9 .
H7A C7 H7B 107.7 .
C13 N8 C9 109.5(6) .
C13 N8 C7 114.5(6) .
C9 N8 C7 108.5(6) .
C13 N8 H8 108(3) .
C9 N8 H8 109(3) .
C7 N8 H8 107(3) .
N8 C9 C10 111.3(6) .
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 110.5(6) .
N11 C10 H10A 109.6 .
C9 C10 H10A 109.6 .
N11 C10 H10B 109.6 .
C9 C10 H10B 109.6 .
H10A C10 H10B 108.1 .
C12 N11 C10 108.5(6) .
C12 N11 C14 112.0(6) .
C10 N11 C14 107.4(6) .
N11 C12 C13 110.3(7) .
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 111.0(6) .
N8 C13 H13A 109.4 .
C12 C13 H13A 109.4 .
N8 C13 H13B 109.4 .
C12 C13 H13B 109.4 .
H13A C13 H13B 108 .
N11 C14 C15 114.3(6) .
N11 C14 H14A 108.7 .
C15 C14 H14A 108.7 .
N11 C14 H14B 108.7 .
C15 C14 H14B 108.7 .
H14A C14 H14B 107.6 .
C16 C15 C20 119.7(7) .
C16 C15 C14 118.3(7) .
C20 C15 C14 121.7(7) .
C17 C16 C15 122.0(7) .
C17 C16 H16 119 .
C15 C16 H16 119 .
C18 C17 C16 118.4(8) .
C18 C17 H17 120.8 .
C16 C17 H17 120.8 .
C17 C18 C19 121.9(7) .
C17 C18 H18 119.1 .
C19 C18 H18 119.1 .
C18 C19 C20 120.1(7) .
C18 C19 C21 118.8(7) .
C20 C19 C21 121.1(7) .
N44 C20 C15 119.7(7) .
N44 C20 C19 122.4(7) .
C15 C20 C19 117.8(7) .
C19 C21 N22 113.7(6) .
C19 C21 H21A 108.8 .
N22 C21 H21A 108.8 .
C19 C21 H21B 108.8 .
N22 C21 H21B 108.8 .
H21A C21 H21B 107.7 .
C27 N22 C23 111.0(6) .
C27 N22 C21 112.6(6) .
C23 N22 C21 108.8(6) .
C27 N22 H22 108.1 .
C23 N22 H22 108.1 .
C21 N22 H22 108.1 .
N22 C23 C24 109.4(7) .
N22 C23 H23A 109.8 .
C24 C23 H23A 109.8 .
N22 C23 H23B 109.8 .
C24 C23 H23B 109.8 .
H23A C23 H23B 108.2 .
N25 C24 C23 109.7(6) .
N25 C24 H24A 109.7 .
C23 C24 H24A 109.7 .
N25 C24 H24B 109.7 .
C23 C24 H24B 109.7 .
H24A C24 H24B 108.2 .
C28 N25 C24 111.8(6) .
C28 N25 C26 111.6(7) .
C24 N25 C26 108.4(6) .
N25 C26 C27 108.9(7) .
N25 C26 H26A 109.9 .
C27 C26 H26A 109.9 .
N25 C26 H26B 109.9 .
C27 C26 H26B 109.9 .
H26A C26 H26B 108.3 .
C26 C27 N22 111.1(6) .
C26 C27 H27A 109.4 .
N22 C27 H27A 109.4 .
C26 C27 H27B 109.4 .
N22 C27 H27B 109.4 .
H27A C27 H27B 108 .
N25 C28 C29 112.9(6) .
N25 C28 H28A 109 .
C29 C28 H28A 109 .
N25 C28 H28B 109 .
C29 C28 H28B 109 .
H28A C28 H28B 107.8 .
C30 C29 C34 120.5(8) .
C30 C29 C28 118.1(7) .
C34 C29 C28 121.4(7) .
C31 C30 C29 121.6(8) .
C31 C30 H30 119.2 .
C29 C30 H30 119.2 .
C30 C31 C32 118.5(8) .
C30 C31 H31 120.8 .
C32 C31 H31 120.8 .
C31 C32 C33 121.8(8) .
C31 C32 H32 119.1 .
C33 C32 H32 119.1 .
C32 C33 C34 119.2(7) .
C32 C33 C35 118.7(7) .
C34 C33 C35 122.1(7) .
C29 C34 N45 120.1(7) .
C29 C34 C33 118.2(7) .
N45 C34 C33 121.6(7) .
C33 C35 N36 114.1(6) .
C33 C35 H35A 108.7 .
N36 C35 H35A 108.7 .
C33 C35 H35B 108.7 .
N36 C35 H35B 108.7 .
H35A C35 H35B 107.6 .
C41 N36 C37 111.8(6) .
C41 N36 C35 112.1(6) .
C37 N36 C35 109.6(6) .
C41 N36 H36 110(6) .
C37 N36 H36 103(6) .
C35 N36 H36 109(5) .
N36 C37 C38 110.8(6) .
N36 C37 H37A 109.5 .
C38 C37 H37A 109.5 .
N36 C37 H37B 109.5 .
C38 C37 H37B 109.5 .
H37A C37 H37B 108.1 .
N39 C38 C37 110.2(6) .
N39 C38 H38A 109.6 .
C37 C38 H38A 109.6 .
N39 C38 H38B 109.6 .
C37 C38 H38B 109.6 .
H38A C38 H38B 108.1 .
C40 N39 C38 108.4(6) .
C40 N39 C42 112.4(6) .
C38 N39 C42 109.5(6) .
N39 C40 C41 110.0(7) .
N39 C40 H40A 109.7 .
C41 C40 H40A 109.7 .
N39 C40 H40B 109.7 .
C41 C40 H40B 109.7 .
H40A C40 H40B 108.2 .
N36 C41 C40 110.6(6) .
N36 C41 H41A 109.5 .
C40 C41 H41A 109.5 .
N36 C41 H41B 109.5 .
C40 C41 H41B 109.5 .
H41A C41 H41B 108.1 .
N39 C42 C1 112.6(6) .
N39 C42 H42A 109.1 .
C1 C42 H42A 109.1 .
N39 C42 H42B 109.1 .
C1 C42 H42B 109.1 .
H42A C42 H42B 107.8 .
C6 N43 H43A 108.9 .
C6 N43 H43B 109.2 .
H43A N43 H43B 109.5 .
C20 N44 H44B 108.9 .
C20 N44 H44C 108.9 .
H44B N44 H44C 109.5 .
C34 N45 I70 124.7(5) .
C34 N45 H45B 109.5 .
I70 N45 H45B 97.8 .
C34 N45 H45C 109.3 .
I70 N45 H45C 105 .
H45B N45 H45C 109.5 .
C48 C47 C56 117.3(11) .
C48 C47 I46 121.4(8) .
C56 C47 I46 121.3(9) .
F49 C48 C47 120.0(11) .
F49 C48 C50 118.2(10) .
C47 C48 C50 121.8(10) .
F51 C50 C52 120.8(11) .
F51 C50 C48 119.0(10) .
C52 C50 C48 120.0(10) .
C54 C52 C50 118.8(11) .
C54 C52 I53 120.2(8) .
C50 C52 I53 120.8(8) .
C52 I53 Cl2 168.7(3) .
F55 C54 C52 121.1(11) .
F55 C54 C56 117.9(11) .
C52 C54 C56 121.0(11) .
F57 C56 C54 118.4(11) .
F57 C56 C47 120.5(12) .
C54 C56 C47 121.1(11) .
C68 C59 C60 118.5(9) .
C68 C59 I58 122.1(7) .
C60 C59 I58 119.3(7) .
F61 C60 C59 121.7(9) .
F61 C60 C62 117.8(9) .
C59 C60 C62 120.5(9) .
F63 C62 C64 119.5(9) .
F63 C62 C60 119.2(8) .
C64 C62 C60 121.2(8) .
C62 C64 C66 116.9(9) .
C62 C64 I65 120.1(7) .
C66 C64 I65 123.0(7) .
C64 I65 Cl1 170.5(2) .
F67 C66 C68 120.7(8) .
F67 C66 C64 118.5(8) .
C68 C66 C64 120.7(8) .
F69 C68 C59 120.2(9) .
F69 C68 C66 117.7(8) .
C59 C68 C66 122.1(8) .
C71 I70 N45 169.1(3) .
C80 C71 C72 116.8(8) .
C80 C71 I70 122.6(7) .
C72 C71 I70 120.6(7) .
F73 C72 C74 119.0(8) .
F73 C72 C71 119.2(8) .
C74 C72 C71 121.8(8) .
F75 C74 C72 118.0(8) .
F75 C74 C76 120.9(8) .
C72 C74 C76 121.1(8) .
C78 C76 C74 117.6(8) .
C78 C76 I77 123.4(7) .
C74 C76 I77 118.9(7) .
F79 C78 C80 118.6(8) .
F79 C78 C76 119.9(8) .
C80 C78 C76 121.4(8) .
F81 C80 C78 119.0(8) .
F81 C80 C71 119.8(9) .
C78 C80 C71 121.2(8) .
C83 I82 Cl3 171.8(3) 4_665
C92 C83 C84 116.5(8) .
C92 C83 I82 121.6(7) .
C84 C83 I82 121.9(7) .
F85 C84 C86 118.4(9) .
F85 C84 C83 119.1(8) .
C86 C84 C83 122.5(9) .
F87 C86 C88 121.1(9) .
F87 C86 C84 118.8(9) .
C88 C86 C84 120.1(9) .
C86 C88 C90 119.1(9) .
C86 C88 I89 120.8(8) .
C90 C88 I89 120.1(8) .
F91 C90 C92 118.1(9) .
F91 C90 C88 121.3(9) .
C92 C90 C88 120.6(9) .
F93 C92 C90 119.0(8) .
F93 C92 C83 119.8(8) .
C90 C92 C83 121.2(9) .
C95 I94 Cl1 172.6(2) .
C96 C95 C104 116.9(7) .
C96 C95 I94 120.0(6) .
C104 C95 I94 123.1(6) .
F97 C96 C98 118.9(7) .
F97 C96 C95 119.9(7) .
C98 C96 C95 121.2(7) .
F99 C98 C100 120.5(7) .
F99 C98 C96 118.1(7) .
C100 C98 C96 121.4(7) .
C98 C100 C102 118.3(8) .
C98 C100 I101 119.9(6) .
C102 C100 I101 121.8(6) .
C100 I101 Cl3 173.8(2) 2
F103 C102 C104 117.9(7) .
F103 C102 C100 121.4(8) .
C104 C102 C100 120.6(8) .
F105 C104 C102 119.8(8) .
F105 C104 C95 118.6(8) .
C102 C104 C95 121.6(7) .
C107 I106 Cl2 175.6(3) 2_655
C116 C107 C108 117.7(9) .
C116 C107 I106 121.0(7) .
C108 C107 I106 121.3(7) .
F109 C108 C110 119.8(9) .
F109 C108 C107 120.0(9) .
C110 C108 C107 120.2(9) .
C108 C110 F111 117.8(9) .
C108 C110 C112 122.3(9) .
F111 C110 C112 119.9(8) .
C110 C112 C114 117.3(9) .
C110 C112 I113 121.5(7) .
C114 C112 I113 121.2(7) .
F115 C114 C116 118.0(9) .
F115 C114 C112 120.5(9) .
C116 C114 C112 121.5(9) .
F117 C116 C107 120.8(9) .
F117 C116 C114 118.1(9) .
C107 C116 C114 121.1(9) .
I94 Cl1 I65 142.25(8) .
C2A O1A H1A 109.5 .
O1A C2A C3A 112.7(7) .
O1A C2A H2A1 109.1 .
C3A C2A H2A1 109.1 .
O1A C2A H2A2 109.1 .
C3A C2A H2A2 109.1 .
H2A1 C2A H2A2 107.8 .
C2A C3A H3A1 109.5 .
C2A C3A H3A2 109.5 .
H3A1 C3A H3A2 109.5 .
C2A C3A H3A3 109.5 .
H3A1 C3A H3A3 109.5 .
H3A2 C3A H3A3 109.5 .
C2B O1B H1B 109.5 .
O1B C2B C3B 113.7(10) .
O1B C2B H2B1 108.8 .
C3B C2B H2B1 108.8 .
O1B C2B H2B2 108.8 .
C3B C2B H2B2 108.8 .
H2B1 C2B H2B2 107.7 .
C2B C3B H3B1 109.5 .
C2B C3B H3B2 109.5 .
H3B1 C3B H3B2 109.5 .
C2B C3B H3B3 109.5 .
H3B1 C3B H3B3 109.5 .
H3B2 C3B H3B3 109.5 .
C2C O1C H1C 109.5 .
O1C C2C C3C 101.5(14) .
O1C C2C H2C1 111.5 .
C3C C2C H2C1 111.5 .
O1C C2C H2C2 111.5 .
C3C C2C H2C2 111.5 .
H2C1 C2C H2C2 109.3 .
C2C C3C H3C1 109.5 .
C2C C3C H3C2 109.5 .
H3C1 C3C H3C2 109.5 .
C2C C3C H3C3 109.5 .
H3C1 C3C H3C3 109.5 .
H3C2 C3C H3C3 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 1.367(12) .
C1 C6 1.429(11) .
C1 C42 1.512(11) .
C2 C3 1.381(11) .
C2 H2 0.95 .
C3 C4 1.384(12) .
C3 H3 0.95 .
C4 C5 1.394(11) .
C4 H4 0.95 .
C5 C6 1.409(10) .
C5 C7 1.501(11) .
C6 N43 1.381(10) .
C7 N8 1.515(9) .
C7 H7A 0.99 .
C7 H7B 0.99 .
N8 C13 1.504(9) .
N8 C9 1.504(10) .
N8 H8 0.92(3) .
C9 C10 1.523(11) .
C9 H9A 0.99 .
C9 H9B 0.99 .
C10 N11 1.468(9) .
C10 H10A 0.99 .
C10 H10B 0.99 .
N11 C12 1.462(10) .
N11 C14 1.476(10) .
C12 C13 1.512(11) .
C12 H12A 0.99 .
C12 H12B 0.99 .
C13 H13A 0.99 .
C13 H13B 0.99 .
C14 C15 1.512(10) .
C14 H14A 0.99 .
C14 H14B 0.99 .
C15 C16 1.398(11) .
C15 C20 1.415(11) .
C16 C17 1.389(11) .
C16 H16 0.95 .
C17 C18 1.375(11) .
C17 H17 0.95 .
C18 C19 1.394(11) .
C18 H18 0.95 .
C19 C20 1.426(11) .
C19 C21 1.500(10) .
C20 N44 1.367(11) .
C21 N22 1.511(10) .
C21 H21A 0.99 .
C21 H21B 0.99 .
N22 C27 1.499(10) .
N22 C23 1.505(9) .
N22 H22 0.93 .
C23 C24 1.518(11) .
C23 H23A 0.99 .
C23 H23B 0.99 .
C24 N25 1.467(10) .
C24 H24A 0.99 .
C24 H24B 0.99 .
N25 C28 1.464(10) .
N25 C26 1.478(10) .
C26 C27 1.493(11) .
C26 H26A 0.99 .
C26 H26B 0.99 .
C27 H27A 0.99 .
C27 H27B 0.99 .
C28 C29 1.524(11) .
C28 H28A 0.99 .
C28 H28B 0.99 .
C29 C30 1.387(12) .
C29 C34 1.394(11) .
C30 C31 1.365(12) .
C30 H30 0.95 .
C31 C32 1.374(12) .
C31 H31 0.95 .
C32 C33 1.400(12) .
C32 H32 0.95 .
C33 C34 1.405(11) .
C33 C35 1.506(11) .
C34 N45 1.399(10) .
C35 N36 1.514(9) .
C35 H35A 0.99 .
C35 H35B 0.99 .
N36 C41 1.492(9) .
N36 C37 1.501(10) .
N36 H36 0.91(2) .
C37 C38 1.517(10) .
C37 H37A 0.99 .
C37 H37B 0.99 .
C38 N39 1.469(10) .
C38 H38A 0.99 .
C38 H38B 0.99 .
N39 C40 1.468(10) .
N39 C42 1.477(10) .
C40 C41 1.517(11) .
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 0.9101 .
N43 H43B 0.9101 .
N44 H44B 0.9101 .
N44 H44C 0.9103 .
N45 I70 2.995(7) .
N45 H45B 0.9103 .
N45 H45C 0.9101 .
I46 C47 2.071(11) .
C47 C48 1.354(16) .
C47 C56 1.392(16) .
C48 F49 1.340(12) .
C48 C50 1.400(16) .
C50 F51 1.332(13) .
C50 C52 1.369(15) .
C52 C54 1.363(15) .
C52 I53 2.104(11) .
I53 Cl2 3.289(2) .
C54 F55 1.326(13) .
C54 C56 1.377(18) .
C56 F57 1.340(13) .
I58 C59 2.083(9) .
C59 C68 1.368(13) .
C59 C60 1.370(13) .
C60 F61 1.319(11) .
C60 C62 1.396(14) .
C62 F63 1.319(11) .
C62 C64 1.393(13) .
C64 C66 1.401(12) .
C64 I65 2.080(9) .
I65 Cl1 3.216(2) .
C66 F67 1.323(11) .
C66 C68 1.372(13) .
C68 F69 1.350(10) .
I70 C71 2.096(9) .
C71 C80 1.387(13) .
C71 C72 1.391(13) .
C72 F73 1.349(10) .
C72 C74 1.365(13) .
C74 F75 1.332(10) .
C74 C76 1.383(12) .
C76 C78 1.378(13) .
C76 I77 2.081(9) .
C78 F79 1.343(10) .
C78 C80 1.377(13) .
C80 F81 1.346(10) .
I82 C83 2.087(8) .
I82 Cl3 3.229(2) 4_665
C83 C92 1.387(12) .
C83 C84 1.387(13) .
C84 F85 1.339(11) .
C84 C86 1.373(13) .
C86 F87 1.334(11) .
C86 C88 1.362(15) .
C88 C90 1.382(15) .
C88 I89 2.095(10) .
C90 F91 1.340(11) .
C90 C92 1.381(12) .
C92 F93 1.342(10) .
I94 C95 2.095(8) .
I94 Cl1 3.128(2) .
C95 C96 1.390(11) .
C95 C104 1.395(12) .
C96 F97 1.340(9) .
C96 C98 1.379(11) .
C98 F99 1.344(9) .
C98 C100 1.374(12) .
C100 C102 1.383(12) .
C100 I101 2.102(8) .
I101 Cl3 3.159(2) 2
C102 F103 1.328(10) .
C102 C104 1.380(12) .
C104 F105 1.344(9) .
I106 C107 2.095(9) .
I106 Cl2 3.221(2) 2_655
C107 C116 1.364(14) .
C107 C108 1.401(14) .
C108 F109 1.348(11) .
C108 C110 1.358(13) .
C110 F111 1.365(11) .
C110 C112 1.368(13) .
C112 C114 1.375(14) .
C112 I113 2.067(10) .
C114 F115 1.338(11) .
C114 C116 1.370(14) .
C116 F117 1.337(11) .
O1A C2A 1.442(10) .
O1A H1A 0.84 .
C2A C3A 1.503(12) .
C2A H2A1 0.99 .
C2A H2A2 0.99 .
C3A H3A1 0.98 .
C3A H3A2 0.98 .
C3A H3A3 0.98 .
O1B C2B 1.438(11) .
O1B H1B 0.84 .
C2B C3B 1.482(13) .
C2B H2B1 0.99 .
C2B H2B2 0.99 .
C3B H3B1 0.98 .
C3B H3B2 0.98 .
C3B H3B3 0.98 .
O1C C2C 1.428(15) .
O1C H1C 0.84 .
C2C C3C 1.447(15) .
C2C H2C1 0.99 .
C2C H2C2 0.99 .
C3C H3C1 0.98 .
C3C H3C2 0.98 .
C3C H3C3 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
N8 H8 O1A 0.92(3) 1.86(3) 2.775(8) 170(4) .
N22 H22 Cl3 0.93 2.23 3.084(7) 151.7 .
N36 H36 Cl2 0.91(2) 2.28(3) 3.158(7) 163(8) .
N43 H43A O1B 0.91 2.23 3.108(10) 162.1 .
N43 H43B N39 0.91 2.23 2.982(9) 140.1 .
N44 H44B O1C 0.91 2.41 3.278(14) 159.6 .
N44 H44C N11 0.91 2.12 2.906(9) 143.9 .
N45 H45C N25 0.91 2.08 2.856(10) 142.8 .
O1A H1A Cl3 0.84 2.42 3.148(6) 145.2 1_655
O1B H1B Cl1 0.84 2.39 3.197(7) 162.4 .
O1C H1C Cl1 0.84 2.31 3.087(10) 154.1 .
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 0.2(13)
C42 C1 C2 C3 176.4(8)
C1 C2 C3 C4 -3.4(13)
C2 C3 C4 C5 4.3(13)
C3 C4 C5 C6 -1.8(12)
C3 C4 C5 C7 180.0(7)
C4 C5 C6 N43 -178.6(7)
C7 C5 C6 N43 -0.5(12)
C4 C5 C6 C1 -1.5(11)
C7 C5 C6 C1 176.7(7)
C2 C1 C6 N43 179.6(8)
C42 C1 C6 N43 3.4(11)
C2 C1 C6 C5 2.3(11)
C42 C1 C6 C5 -173.9(7)
C4 C5 C7 N8 -63.8(9)
C6 C5 C7 N8 118.0(8)
C5 C7 N8 C13 -48.5(9)
C5 C7 N8 C9 -171.1(6)
C13 N8 C9 C10 52.9(8)
C7 N8 C9 C10 178.5(6)
N8 C9 C10 N11 -57.6(9)
C9 C10 N11 C12 61.4(8)
C9 C10 N11 C14 -177.4(7)
C10 N11 C12 C13 -62.6(8)
C14 N11 C12 C13 179.1(6)
C9 N8 C13 C12 -54.0(8)
C7 N8 C13 C12 -176.1(6)
N11 C12 C13 N8 59.8(8)
C12 N11 C14 C15 -59.1(9)
C10 N11 C14 C15 -178.1(7)
N11 C14 C15 C16 131.7(8)
N11 C14 C15 C20 -53.8(10)
C20 C15 C16 C17 -0.8(12)
C14 C15 C16 C17 173.9(8)
C15 C16 C17 C18 -1.5(13)
C16 C17 C18 C19 1.6(12)
C17 C18 C19 C20 0.4(12)
C17 C18 C19 C21 -178.6(7)
C16 C15 C20 N44 179.5(7)
C14 C15 C20 N44 5.1(12)
C16 C15 C20 C19 2.7(11)
C14 C15 C20 C19 -171.7(7)
C18 C19 C20 N44 -179.3(8)
C21 C19 C20 N44 -0.3(12)
C18 C19 C20 C15 -2.6(11)
C21 C19 C20 C15 176.4(7)
C18 C19 C21 N22 -60.6(9)
C20 C19 C21 N22 120.4(8)
C19 C21 N22 C27 -54.1(9)
C19 C21 N22 C23 -177.6(6)
C27 N22 C23 C24 53.1(8)
C21 N22 C23 C24 177.6(6)
N22 C23 C24 N25 -58.9(8)
C23 C24 N25 C28 -172.0(7)
C23 C24 N25 C26 64.6(8)
C28 N25 C26 C27 172.3(6)
C24 N25 C26 C27 -64.2(8)
N25 C26 C27 N22 59.1(8)
C23 N22 C27 C26 -54.2(9)
C21 N22 C27 C26 -176.5(6)
C24 N25 C28 C29 175.5(7)
C26 N25 C28 C29 -62.9(9)
N25 C28 C29 C30 127.8(8)
N25 C28 C29 C34 -51.5(10)
C34 C29 C30 C31 -3.6(12)
C28 C29 C30 C31 177.1(7)
C29 C30 C31 C32 -0.4(12)
C30 C31 C32 C33 1.6(12)
C31 C32 C33 C34 1.3(11)
C31 C32 C33 C35 -177.1(7)
C30 C29 C34 N45 -177.1(7)
C28 C29 C34 N45 2.2(11)
C30 C29 C34 C33 6.4(11)
C28 C29 C34 C33 -174.3(7)
C32 C33 C34 C29 -5.2(10)
C35 C33 C34 C29 173.1(7)
C32 C33 C34 N45 178.3(7)
C35 C33 C34 N45 -3.4(11)
C32 C33 C35 N36 -55.0(9)
C34 C33 C35 N36 126.6(7)
C33 C35 N36 C41 -50.4(9)
C33 C35 N36 C37 -175.2(6)
C41 N36 C37 C38 51.4(8)
C35 N36 C37 C38 176.3(6)
N36 C37 C38 N39 -56.9(8)
C37 C38 N39 C40 63.0(8)
C37 C38 N39 C42 -174.1(7)
C38 N39 C40 C41 -63.6(8)
C42 N39 C40 C41 175.2(6)
C37 N36 C41 C40 -52.0(8)
C35 N36 C41 C40 -175.5(7)
N39 C40 C41 N36 58.3(8)
C40 N39 C42 C1 -57.7(9)
C38 N39 C42 C1 -178.2(7)
C2 C1 C42 N39 119.1(8)
C6 C1 C42 N39 -64.8(10)
C29 C34 N45 I70 -101.9(7)
C33 C34 N45 I70 74.5(8)
C56 C47 C48 F49 -179.5(12)
I46 C47 C48 F49 0.4(16)
C56 C47 C48 C50 1.3(19)
I46 C47 C48 C50 -178.8(9)
F49 C48 C50 F51 2.5(18)
C47 C48 C50 F51 -178.2(12)
F49 C48 C50 C52 178.4(11)
C47 C48 C50 C52 -2(2)
F51 C50 C52 C54 176.8(12)
C48 C50 C52 C54 0.9(19)
F51 C50 C52 I53 -8.4(17)
C48 C50 C52 I53 175.7(9)
C54 C52 I53 Cl2 92.1(18)
C50 C52 I53 Cl2 -82.7(18)
C50 C52 C54 F55 177.8(13)
I53 C52 C54 F55 3.0(19)
C50 C52 C54 C56 1(2)
I53 C52 C54 C56 -173.5(11)
F55 C54 C56 F57 3(2)
C52 C54 C56 F57 179.1(13)
F55 C54 C56 C47 -179.0(13)
C52 C54 C56 C47 -2(2)
C48 C47 C56 F57 179.6(13)
I46 C47 C56 F57 -0.3(19)
C48 C47 C56 C54 1(2)
I46 C47 C56 C54 -178.8(11)
C68 C59 C60 F61 179.0(10)
I58 C59 C60 F61 0.7(15)
C68 C59 C60 C62 0.5(16)
I58 C59 C60 C62 -177.8(8)
F61 C60 C62 F63 1.0(17)
C59 C60 C62 F63 179.6(10)
F61 C60 C62 C64 179.7(10)
C59 C60 C62 C64 -1.8(17)
F63 C62 C64 C66 -179.1(9)
C60 C62 C64 C66 2.3(15)
F63 C62 C64 I65 2.0(14)
C60 C62 C64 I65 -176.6(8)
C62 C64 C66 F67 178.1(9)
I65 C64 C66 F67 -3.0(12)
C62 C64 C66 C68 -1.6(14)
I65 C64 C66 C68 177.2(7)
C60 C59 C68 F69 178.8(9)
I58 C59 C68 F69 -2.9(12)
C60 C59 C68 C66 0.1(14)
I58 C59 C68 C66 178.4(7)
F67 C66 C68 F69 2.0(13)
C64 C66 C68 F69 -178.3(8)
F67 C66 C68 C59 -179.3(9)
C64 C66 C68 C59 0.4(14)
C34 N45 I70 C71 -74.2(17)
N45 I70 C71 C80 -104.8(16)
N45 I70 C71 C72 74.5(17)
C80 C71 C72 F73 179.8(8)
I70 C71 C72 F73 0.5(11)
C80 C71 C72 C74 -0.9(13)
I70 C71 C72 C74 179.7(7)
F73 C72 C74 F75 0.1(13)
C71 C72 C74 F75 -179.1(8)
F73 C72 C74 C76 179.6(8)
C71 C72 C74 C76 0.3(14)
F75 C74 C76 C78 -179.8(8)
C72 C74 C76 C78 0.8(14)
F75 C74 C76 I77 -1.7(12)
C72 C74 C76 I77 178.9(7)
C74 C76 C78 F79 -179.9(8)
I77 C76 C78 F79 2.2(12)
C74 C76 C78 C80 -1.2(14)
I77 C76 C78 C80 -179.2(7)
F79 C78 C80 F81 -1.4(14)
C76 C78 C80 F81 180.0(9)
F79 C78 C80 C71 179.2(8)
C76 C78 C80 C71 0.6(15)
C72 C71 C80 F81 -178.9(8)
I70 C71 C80 F81 0.4(13)
C72 C71 C80 C78 0.5(14)
I70 C71 C80 C78 179.8(7)
C92 C83 C84 F85 -178.3(8)
I82 C83 C84 F85 2.2(12)
C92 C83 C84 C86 -0.1(14)
I82 C83 C84 C86 -179.5(7)
F85 C84 C86 F87 -1.3(14)
C83 C84 C86 F87 -179.6(8)
F85 C84 C86 C88 178.4(9)
C83 C84 C86 C88 0.1(15)
F87 C86 C88 C90 179.6(9)
C84 C86 C88 C90 -0.1(15)
F87 C86 C88 I89 -0.7(13)
C84 C86 C88 I89 179.6(7)
C86 C88 C90 F91 179.9(9)
I89 C88 C90 F91 0.1(13)
C86 C88 C90 C92 0.1(15)
I89 C88 C90 C92 -179.6(7)
F91 C90 C92 F93 -1.8(13)
C88 C90 C92 F93 177.9(8)
F91 C90 C92 C83 -179.9(8)
C88 C90 C92 C83 -0.1(14)
C84 C83 C92 F93 -177.9(8)
I82 C83 C92 F93 1.5(11)
C84 C83 C92 C90 0.1(13)
I82 C83 C92 C90 179.5(7)
C104 C95 C96 F97 176.9(7)
I94 C95 C96 F97 -5.1(10)
C104 C95 C96 C98 -1.8(12)
I94 C95 C96 C98 176.2(6)
F97 C96 C98 F99 1.5(11)
C95 C96 C98 F99 -179.8(7)
F97 C96 C98 C100 -177.7(7)
C95 C96 C98 C100 1.0(13)
F99 C98 C100 C102 -179.7(7)
C96 C98 C100 C102 -0.6(13)
F99 C98 C100 I101 -1.5(11)
C96 C98 C100 I101 177.6(6)
C98 C100 C102 F103 178.1(8)
I101 C100 C102 F103 0.0(12)
C98 C100 C102 C104 1.0(13)
I101 C100 C102 C104 -177.2(6)
F103 C102 C104 F105 1.4(13)
C100 C102 C104 F105 178.6(8)
F103 C102 C104 C95 -179.1(8)
C100 C102 C104 C95 -1.9(14)
C96 C95 C104 F105 -178.2(7)
I94 C95 C104 F105 3.8(11)
C96 C95 C104 C102 2.2(13)
I94 C95 C104 C102 -175.7(7)
C116 C107 C108 F109 179.0(8)
I106 C107 C108 F109 2.7(12)
C116 C107 C108 C110 -0.1(14)
I106 C107 C108 C110 -176.3(7)
F109 C108 C110 F111 2.4(14)
C107 C108 C110 F111 -178.5(8)
F109 C108 C110 C112 -178.9(9)
C107 C108 C110 C112 0.2(15)
C108 C110 C112 C114 -0.1(15)
F111 C110 C112 C114 178.6(9)
C108 C110 C112 I113 177.7(7)
F111 C110 C112 I113 -3.6(13)
C110 C112 C114 F115 180.0(9)
I113 C112 C114 F115 2.1(14)
C110 C112 C114 C116 -0.1(15)
I113 C112 C114 C116 -177.9(8)
C108 C107 C116 F117 -179.6(8)
I106 C107 C116 F117 -3.4(12)
C108 C107 C116 C114 -0.1(14)
I106 C107 C116 C114 176.1(7)
F115 C114 C116 F117 -0.3(14)
C112 C114 C116 F117 179.8(9)
F115 C114 C116 C107 -179.8(9)
C112 C114 C116 C107 0.2(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139144777
