#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/60/4036090.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_4036090
loop_
_publ_author_name
'Royakkers, Jeroen'
'Minotto, Alessandro'
'Congrave, Daniel G.'
'Zeng, Weixuan'
'Patel, Adil'
'Bond, Andrew D.'
'Bučar, Dejan-Krešimir'
'Cacialli, Franco'
'Bronstein, Hugo'
_publ_section_title
;
 Doubly Encapsulated Perylene Diimides: Effect of Molecular Encapsulation
 on Photophysical Properties.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02597
_journal_year                    2019
_chemical_formula_moiety         'C120 H162 N2 O12, 2(C H Cl3)'
_chemical_formula_sum            'C122 H164 Cl6 N2 O12'
_chemical_formula_weight         2063.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                91.916(3)
_cell_angle_beta                 92.930(3)
_cell_angle_gamma                101.564(3)
_cell_formula_units_Z            1
_cell_length_a                   9.9083(4)
_cell_length_b                   15.1863(6)
_cell_length_c                   19.2030(8)
_cell_measurement_reflns_used    3319
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      54.20
_cell_measurement_theta_min      2.31
_cell_volume                     2824.3(2)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1152
_diffrn_reflns_av_unetI/netI     0.1174
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21609
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        54.423
_diffrn_reflns_theta_max         54.423
_diffrn_reflns_theta_min         2.306
_diffrn_source                   'Incoatec I\mS Cu microsource'
_exptl_absorpt_coefficient_mu    1.859
_exptl_absorpt_correction_T_max  0.7507
_exptl_absorpt_correction_T_min  0.5777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       lath
_exptl_crystal_F_000             1108
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_refine_diff_density_max         1.567
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.158
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     640
_refine_ls_number_reflns         6916
_refine_ls_number_restraints     439
_refine_ls_restrained_S_all      2.179
_refine_ls_R_factor_all          0.2857
_refine_ls_R_factor_gt           0.1955
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4227
_refine_ls_wR_factor_ref         0.4526
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3626
_reflns_number_total             6916
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b02597_si_001.cif
_cod_data_source_block           PDI_Encap
_cod_database_code               4036090
_cambridge_user_name             'Jeroen Royakkers'
_cambridge_user_crsid            jr748
_cambridge_supervisor_name       'Hugo Bronstein'
_cambridge_supervisor_crsid      hab60
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             JR434
_cambridge_data_id               HB_B2_0003
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.562
_shelx_estimated_absorpt_t_max   0.982
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3674(10) 0.1022(6) 0.2543(5) 0.071(3) Uani 1 1 d . . . .
O2 O 0.3978(9) 0.3344(6) 0.4093(4) 0.065(3) Uani 1 1 d . . . .
O3 O 0.0178(7) -0.0674(6) 0.2185(3) 0.052(2) Uani 1 1 d D . . .
O4 O 0.4380(6) -0.0620(6) 0.3382(4) 0.053(2) Uani 1 1 d D . . .
O5 O 0.0440(8) 0.3558(6) 0.4535(5) 0.063(2) Uani 1 1 d D . . .
O6 O 0.4251(9) 0.3016(9) 0.5883(5) 0.096(4) Uani 1 1 d D . . .
N1 N 0.3799(7) 0.2183(6) 0.3328(5) 0.042(2) Uani 1 1 d . . . .
C1 C 0.3297(11) 0.1272(8) 0.3093(6) 0.045(3) Uani 1 1 d . U . .
C2 C 0.3471(10) 0.2562(9) 0.3939(6) 0.048(3) Uani 1 1 d . U . .
C3 C 0.2330(9) 0.0711(7) 0.3542(5) 0.035(3) Uani 1 1 d . U . .
C4 C 0.2435(10) 0.1992(8) 0.4371(6) 0.041(3) Uani 1 1 d . U . .
C5 C 0.1845(9) -0.0199(8) 0.3350(5) 0.036(3) Uani 1 1 d . U . .
C6 C 0.1915(9) 0.1085(7) 0.4155(5) 0.030(2) Uani 1 1 d . U . .
C7 C 0.1982(9) 0.2367(8) 0.4964(6) 0.042(3) Uani 1 1 d . U . .
C8 C 0.0899(10) -0.0705(8) 0.3758(5) 0.039(3) Uani 1 1 d . U . .
H8A H 0.054253 -0.131662 0.361569 0.047 Uiso 1 1 calc R U . .
C9 C 0.0960(8) 0.0556(7) 0.4573(5) 0.030(2) Uani 1 1 d . U . .
C10 C 0.1061(9) 0.1817(8) 0.5355(6) 0.041(3) Uani 1 1 d . U . .
H10A H 0.076579 0.207551 0.576366 0.049 Uiso 1 1 calc R U . .
C11 C 0.0438(8) -0.0366(7) 0.4369(5) 0.030(2) Uani 1 1 d . U . .
C12 C 0.0537(9) 0.0913(7) 0.5193(5) 0.036(3) Uani 1 1 d . U . .
C13 C 0.2280(10) -0.0686(7) 0.2737(5) 0.039(3) Uani 1 1 d . U . .
C14 C 0.1449(10) -0.0927(8) 0.2165(6) 0.041(3) Uani 1 1 d . U . .
C15 C 0.1859(12) -0.1379(9) 0.1608(7) 0.061(4) Uani 1 1 d . U . .
H15A H 0.125507 -0.154534 0.120357 0.073 Uiso 1 1 calc R U . .
C16 C 0.3125(12) -0.1586(9) 0.1637(7) 0.060(3) Uani 1 1 d . U . .
H16A H 0.339316 -0.190418 0.125054 0.072 Uiso 1 1 calc R U . .
C17 C 0.4045(13) -0.1348(9) 0.2213(7) 0.059(3) Uani 1 1 d . U . .
H17A H 0.494178 -0.148151 0.221979 0.071 Uiso 1 1 calc R U . .
C18 C 0.3616(11) -0.0912(8) 0.2775(6) 0.048(3) Uani 1 1 d . U . .
C19 C 0.2382(11) 0.3351(9) 0.5202(7) 0.053(3) Uani 1 1 d . U . .
C20 C 0.1632(13) 0.3896(9) 0.4968(7) 0.062(4) Uani 1 1 d . U . .
C21 C 0.1980(18) 0.4858(13) 0.5149(10) 0.103(6) Uani 1 1 d . U . .
H21A H 0.145229 0.527595 0.498674 0.124 Uiso 1 1 calc R U . .
C22 C 0.3203(14) 0.5101(10) 0.5597(8) 0.076(4) Uani 1 1 d . U . .
H22A H 0.351059 0.572002 0.572961 0.091 Uiso 1 1 calc R U . .
C23 C 0.3929(16) 0.4543(12) 0.5839(9) 0.091(5) Uani 1 1 d . U . .
H23A H 0.470630 0.475580 0.615407 0.109 Uiso 1 1 calc R U . .
C24 C 0.3572(14) 0.3637(10) 0.5638(7) 0.064(4) Uani 1 1 d . U . .
C25 C -0.0764(9) -0.0832(8) 0.1572(5) 0.060(3) Uani 1 1 d D U . .
H25A H -0.098177 -0.147971 0.142937 0.072 Uiso 1 1 calc R U . .
H25B H -0.035088 -0.048891 0.117958 0.072 Uiso 1 1 calc R U . .
C26 C -0.2057(9) -0.0520(6) 0.1772(6) 0.056(3) Uani 1 1 d D U . .
H26A H -0.280990 -0.076653 0.141748 0.067 Uiso 1 1 calc R U . .
H26B H -0.233174 -0.077572 0.222362 0.067 Uiso 1 1 calc R U . .
C27 C -0.1923(10) 0.0486(6) 0.1838(5) 0.059(3) Uani 1 1 d D U . .
H27A H -0.285971 0.062029 0.184669 0.071 Uiso 1 1 calc R U . .
H27B H -0.150042 0.075173 0.141742 0.071 Uiso 1 1 calc R U . .
C28 C -0.1067(10) 0.0945(6) 0.2483(5) 0.053(3) Uani 1 1 d D U . .
H28A H -0.007529 0.098381 0.241092 0.064 Uiso 1 1 calc R U . .
H28B H -0.130149 0.057760 0.289255 0.064 Uiso 1 1 calc R U . .
C29 C -0.1330(11) 0.1892(6) 0.2630(6) 0.065(4) Uani 1 1 d D U . .
H29A H -0.230117 0.184547 0.275039 0.078 Uiso 1 1 calc R U . .
H29B H -0.119743 0.223558 0.220112 0.078 Uiso 1 1 calc R U . .
C30 C -0.0373(11) 0.2409(6) 0.3227(6) 0.059(3) Uani 1 1 d D U . .
H30A H 0.059622 0.250943 0.309407 0.070 Uiso 1 1 calc R U . .
H30B H -0.044945 0.205187 0.365057 0.070 Uiso 1 1 calc R U . .
C31 C -0.0780(13) 0.3326(7) 0.3384(7) 0.087(5) Uani 1 1 d D U . .
H31A H -0.089453 0.362380 0.294030 0.104 Uiso 1 1 calc R U . .
H31B H -0.167625 0.322264 0.360482 0.104 Uiso 1 1 calc R U . .
C32 C 0.0305(14) 0.3946(7) 0.3867(5) 0.081(4) Uani 1 1 d D U . .
H32A H 0.120475 0.404839 0.364990 0.097 Uiso 1 1 calc R U . .
H32B H 0.003508 0.453571 0.393313 0.097 Uiso 1 1 calc R U . .
C33 C 0.5847(8) -0.0502(8) 0.3347(6) 0.066(4) Uani 1 1 d D U . .
H33A H 0.616967 -0.011034 0.296208 0.079 Uiso 1 1 calc R U . .
H33B H 0.611491 -0.108999 0.326732 0.079 Uiso 1 1 calc R U . .
C34 C 0.6469(11) -0.0064(7) 0.4053(6) 0.066(4) Uani 1 1 d D U . .
H34A H 0.614961 -0.046992 0.442953 0.079 Uiso 1 1 calc R U . .
H34B H 0.748766 0.002860 0.405931 0.079 Uiso 1 1 calc R U . .
C35 C 0.6051(12) 0.0843(7) 0.4187(5) 0.067(4) Uani 1 1 d D U . .
H35A H 0.622682 0.121332 0.377408 0.080 Uiso 1 1 calc R U . .
H35B H 0.505175 0.074231 0.426252 0.080 Uiso 1 1 calc R U . .
C36 C 0.6865(11) 0.1340(7) 0.4824(6) 0.062(4) Uani 1 1 d D U . .
H36A H 0.687958 0.091136 0.520049 0.074 Uiso 1 1 calc R U . .
H36B H 0.783004 0.156233 0.470360 0.074 Uiso 1 1 calc R U . .
C37 C 0.6285(12) 0.2126(8) 0.5095(7) 0.078(4) Uani 1 1 d D U . .
H37A H 0.536412 0.190499 0.527328 0.094 Uiso 1 1 calc R U . .
H37B H 0.618007 0.253140 0.471113 0.094 Uiso 1 1 calc R U . .
C38 C 0.7271(12) 0.2648(9) 0.5687(7) 0.097(5) Uani 1 1 d D U . .
H38A H 0.734433 0.224629 0.607694 0.116 Uiso 1 1 calc R U . .
H38B H 0.820267 0.284098 0.551233 0.116 Uiso 1 1 calc R U . .
C39 C 0.6759(15) 0.3467(8) 0.5952(8) 0.127(7) Uani 1 1 d D U . .
H39A H 0.654479 0.381833 0.555065 0.152 Uiso 1 1 calc R U . .
H39B H 0.749688 0.385430 0.625470 0.152 Uiso 1 1 calc R U . .
C40 C 0.5476(10) 0.3201(11) 0.6362(6) 0.093(5) Uani 1 1 d D U . .
H40A H 0.553510 0.265938 0.662527 0.112 Uiso 1 1 calc R U . .
H40B H 0.541270 0.369516 0.670062 0.112 Uiso 1 1 calc R U . .
C41 C 0.4828(12) 0.2713(8) 0.2916(6) 0.064(4) Uani 1 1 d D U . .
H41A H 0.539547 0.230711 0.272148 0.077 Uiso 1 1 calc R U . .
H41B H 0.544531 0.316110 0.323508 0.077 Uiso 1 1 calc R U . .
C42 C 0.4303(14) 0.3216(12) 0.2310(8) 0.136(8) Uani 1 1 d D U . .
H42A H 0.378295 0.276301 0.195234 0.164 Uiso 1 1 calc R U . .
C43 C 0.5565(18) 0.3777(10) 0.1972(9) 0.151(8) Uani 1 1 d D U . .
H43A H 0.527345 0.425428 0.169777 0.181 Uiso 1 1 calc R U . .
H43B H 0.626230 0.406769 0.234031 0.181 Uiso 1 1 calc R U . .
C44 C 0.6196(15) 0.3156(10) 0.1492(9) 0.117(6) Uani 1 1 d D U . .
H44A H 0.553266 0.291716 0.109459 0.140 Uiso 1 1 calc R U . .
H44B H 0.639149 0.264104 0.175409 0.140 Uiso 1 1 calc R U . .
C45 C 0.7543(18) 0.3685(12) 0.1217(11) 0.156(9) Uani 1 1 d D U . .
H45A H 0.736696 0.423934 0.100360 0.188 Uiso 1 1 calc R U . .
H45B H 0.824200 0.386432 0.160969 0.188 Uiso 1 1 calc R U . .
C46 C 0.8092(19) 0.3111(12) 0.0676(12) 0.167(10) Uani 1 1 d D U . .
H46A H 0.732487 0.279947 0.034993 0.201 Uiso 1 1 calc R U . .
H46B H 0.850525 0.264975 0.091071 0.201 Uiso 1 1 calc R U . .
C47 C 0.919(2) 0.3715(15) 0.0267(14) 0.258(18) Uani 1 1 d D U . .
H47A H 0.874570 0.391403 -0.015708 0.309 Uiso 1 1 calc R U . .
H47B H 0.962455 0.425657 0.055994 0.309 Uiso 1 1 calc R U . .
C48 C 1.028(2) 0.3194(13) 0.0062(16) 0.196(12) Uani 1 1 d D U . .
H48A H 0.988832 0.273093 -0.030776 0.235 Uiso 1 1 calc R U . .
H48B H 1.058042 0.288552 0.047108 0.235 Uiso 1 1 calc R U . .
C49 C 1.1541(19) 0.3835(13) -0.0206(16) 0.186(11) Uani 1 1 d D U . .
H49A H 1.122206 0.426271 -0.052264 0.223 Uiso 1 1 calc R U . .
H49B H 1.208855 0.418663 0.019331 0.223 Uiso 1 1 calc R U . .
C50 C 1.2435(18) 0.3305(15) -0.0591(14) 0.197(12) Uani 1 1 d D U . .
H50A H 1.203744 0.315354 -0.107388 0.236 Uiso 1 1 calc R U . .
H50B H 1.244132 0.273469 -0.035680 0.236 Uiso 1 1 calc R U . .
C51 C 1.3923(19) 0.3840(17) -0.061(2) 0.257(18) Uani 1 1 d D U . .
H51A H 1.432002 0.400974 -0.013104 0.308 Uiso 1 1 calc R U . .
H51B H 1.393147 0.439696 -0.086609 0.308 Uiso 1 1 calc R U . .
C52 C 1.478(2) 0.325(2) -0.0984(19) 0.256(17) Uani 1 1 d D U . .
H52A H 1.573705 0.358030 -0.100095 0.384 Uiso 1 1 calc R U . .
H52B H 1.477623 0.269878 -0.072761 0.384 Uiso 1 1 calc R U . .
H52C H 1.438889 0.308479 -0.146038 0.384 Uiso 1 1 calc R U . .
C53 C 0.337(3) 0.3821(19) 0.2536(11) 0.239(16) Uani 1 1 d D U . .
H53A H 0.389116 0.428954 0.287270 0.286 Uiso 1 1 calc R U . .
H53B H 0.260273 0.346298 0.278172 0.286 Uiso 1 1 calc R U . .
C54 C 0.275(3) 0.4285(16) 0.1926(12) 0.207(13) Uani 1 1 d D U . .
H54A H 0.336276 0.433233 0.153162 0.248 Uiso 1 1 calc R U A 2
H54B H 0.183564 0.392567 0.176112 0.248 Uiso 1 1 calc R U A 2
C55 C 0.261(3) 0.5225(13) 0.218(2) 0.41(4) Uani 1 1 d D U B 2
H55A H 0.256915 0.523351 0.269789 0.494 Uiso 1 1 calc R U B 2
H55B H 0.343883 0.566323 0.207072 0.494 Uiso 1 1 calc R U B 2
C56 C 0.135(3) 0.553(2) 0.1876(14) 0.35(3) Uani 1 1 d D U . .
H56A H 0.095383 0.513081 0.146566 0.415 Uiso 1 1 calc R U B 2
H56B H 0.162372 0.614785 0.171533 0.415 Uiso 1 1 calc R U B 2
C57 C 0.024(4) 0.5510(17) 0.241(3) 0.53(5) Uani 1 1 d D U . .
H57A H 0.052532 0.524011 0.283647 0.642 Uiso 1 1 calc R U . .
H57B H -0.063616 0.512495 0.221113 0.642 Uiso 1 1 calc R U . .
C58 C -0.002(2) 0.6452(16) 0.259(2) 0.35(3) Uani 1 1 d D U . .
H58A H -0.000465 0.680283 0.216483 0.417 Uiso 1 1 calc R U . .
H58B H 0.072223 0.677264 0.292715 0.417 Uiso 1 1 calc R U . .
C59 C -0.143(3) 0.6367(17) 0.2913(14) 0.200(12) Uani 1 1 d D U . .
H59A H -0.200756 0.576967 0.277567 0.239 Uiso 1 1 calc R U . .
H59B H -0.129106 0.640744 0.342811 0.239 Uiso 1 1 calc R U . .
C60 C -0.2179(19) 0.7102(13) 0.2676(9) 0.111(6) Uani 1 1 d D U . .
H60A H -0.306934 0.702680 0.288994 0.166 Uiso 1 1 calc R U . .
H60B H -0.161649 0.769331 0.281831 0.166 Uiso 1 1 calc R U . .
H60C H -0.233258 0.705590 0.216625 0.166 Uiso 1 1 calc R U . .
C1S C 0.2852(12) 0.0506(9) 0.0772(9) 0.182(11) Uani 1 1 d D U . .
H1S H 0.287056 0.018098 0.121563 0.218 Uiso 1 1 calc R U . .
Cl1 Cl 0.1783(10) 0.1260(7) 0.0853(6) 0.260(5) Uani 1 1 d D . . .
Cl2 Cl 0.2234(14) -0.0271(7) 0.0098(4) 0.340(9) Uani 1 1 d D . . .
Cl3 Cl 0.4491(9) 0.1051(9) 0.0637(7) 0.344(8) Uani 1 1 d D . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_3
C14 O3 C25 119.5(7) .
C18 O4 C33 115.8(8) .
C20 O5 C32 118.3(9) .
C24 O6 C40 125.4(13) .
C2 N1 C1 124.7(9) .
C2 N1 C41 118.5(10) .
C1 N1 C41 116.6(9) .
O1 C1 N1 117.9(10) .
O1 C1 C3 125.5(11) .
N1 C1 C3 116.6(9) .
O2 C2 N1 119.0(10) .
O2 C2 C4 123.1(11) .
N1 C2 C4 117.8(11) .
C5 C3 C6 120.5(9) .
C5 C3 C1 119.0(9) .
C6 C3 C1 120.5(10) .
C7 C4 C6 121.0(9) .
C7 C4 C2 120.0(10) .
C6 C4 C2 119.0(10) .
C8 C5 C3 118.3(9) .
C8 C5 C13 116.3(10) .
C3 C5 C13 125.4(9) .
C3 C6 C4 121.3(9) .
C3 C6 C9 120.5(9) .
C4 C6 C9 118.2(9) .
C10 C7 C4 118.2(10) .
C10 C7 C19 116.9(10) .
C4 C7 C19 124.8(10) .
C5 C8 C11 123.6(11) .
C5 C8 H8A 118.2 .
C11 C8 H8A 118.2 .
C12 C9 C6 121.6(9) .
C12 C9 C11 119.3(9) .
C6 C9 C11 119.1(9) .
C7 C10 C12 124.4(10) .
C7 C10 H10A 117.8 .
C12 C10 H10A 117.8 .
C8 C11 C9 117.9(9) .
C8 C11 C12 123.2(10) 2_556
C9 C11 C12 118.9(9) 2_556
C10 C12 C9 116.5(9) .
C10 C12 C11 121.7(9) 2_556
C9 C12 C11 121.8(9) 2_556
C14 C13 C18 119.5(10) .
C14 C13 C5 121.8(9) .
C18 C13 C5 118.8(10) .
C13 C14 C15 121.1(10) .
C13 C14 O3 114.6(9) .
C15 C14 O3 124.3(10) .
C16 C15 C14 119.7(12) .
C16 C15 H15A 120.1 .
C14 C15 H15A 120.1 .
C15 C16 C17 122.1(12) .
C15 C16 H16A 119.0 .
C17 C16 H16A 119.0 .
C18 C17 C16 117.9(11) .
C18 C17 H17A 121.1 .
C16 C17 H17A 121.1 .
O4 C18 C17 126.1(10) .
O4 C18 C13 114.2(9) .
C17 C18 C13 119.7(11) .
C20 C19 C24 122.9(13) .
C20 C19 C7 118.3(11) .
C24 C19 C7 118.8(13) .
C19 C20 O5 119.7(11) .
C19 C20 C21 121.7(14) .
O5 C20 C21 118.6(14) .
C22 C21 C20 112.4(16) .
C22 C21 H21A 123.8 .
C20 C21 H21A 123.8 .
C23 C22 C21 125.2(16) .
C23 C22 H22A 117.4 .
C21 C22 H22A 117.4 .
C22 C23 C24 120.1(16) .
C22 C23 H23A 119.9 .
C24 C23 H23A 119.9 .
O6 C24 C23 123.4(14) .
O6 C24 C19 118.7(12) .
C23 C24 C19 117.7(16) .
O3 C25 C26 106.4(8) .
O3 C25 H25A 110.4 .
C26 C25 H25A 110.4 .
O3 C25 H25B 110.4 .
C26 C25 H25B 110.4 .
H25A C25 H25B 108.6 .
C27 C26 C25 115.0(7) .
C27 C26 H26A 108.5 .
C25 C26 H26A 108.5 .
C27 C26 H26B 108.5 .
C25 C26 H26B 108.5 .
H26A C26 H26B 107.5 .
C26 C27 C28 115.1(7) .
C26 C27 H27A 108.5 .
C28 C27 H27A 108.5 .
C26 C27 H27B 108.5 .
C28 C27 H27B 108.5 .
H27A C27 H27B 107.5 .
C27 C28 C29 111.6(7) .
C27 C28 H28A 109.3 .
C29 C28 H28A 109.3 .
C27 C28 H28B 109.3 .
C29 C28 H28B 109.3 .
H28A C28 H28B 108.0 .
C28 C29 C30 112.8(7) .
C28 C29 H29A 109.0 .
C30 C29 H29A 109.0 .
C28 C29 H29B 109.0 .
C30 C29 H29B 109.0 .
H29A C29 H29B 107.8 .
C29 C30 C31 109.7(7) .
C29 C30 H30A 109.7 .
C31 C30 H30A 109.7 .
C29 C30 H30B 109.7 .
C31 C30 H30B 109.7 .
H30A C30 H30B 108.2 .
C32 C31 C30 111.9(8) .
C32 C31 H31A 109.2 .
C30 C31 H31A 109.2 .
C32 C31 H31B 109.2 .
C30 C31 H31B 109.2 .
H31A C31 H31B 107.9 .
O5 C32 C31 110.8(10) .
O5 C32 H32A 109.5 .
C31 C32 H32A 109.5 .
O5 C32 H32B 109.5 .
C31 C32 H32B 109.5 .
H32A C32 H32B 108.1 .
O4 C33 C34 105.9(8) .
O4 C33 H33A 110.6 .
C34 C33 H33A 110.6 .
O4 C33 H33B 110.6 .
C34 C33 H33B 110.6 .
H33A C33 H33B 108.7 .
C35 C34 C33 111.2(7) .
C35 C34 H34A 109.4 .
C33 C34 H34A 109.4 .
C35 C34 H34B 109.4 .
C33 C34 H34B 109.4 .
H34A C34 H34B 108.0 .
C36 C35 C34 110.4(7) .
C36 C35 H35A 109.6 .
C34 C35 H35A 109.6 .
C36 C35 H35B 109.6 .
C34 C35 H35B 109.6 .
H35A C35 H35B 108.1 .
C37 C36 C35 113.6(7) .
C37 C36 H36A 108.9 .
C35 C36 H36A 108.9 .
C37 C36 H36B 108.9 .
C35 C36 H36B 108.9 .
H36A C36 H36B 107.7 .
C36 C37 C38 109.5(7) .
C36 C37 H37A 109.8 .
C38 C37 H37A 109.8 .
C36 C37 H37B 109.8 .
C38 C37 H37B 109.8 .
H37A C37 H37B 108.2 .
C39 C38 C37 111.2(8) .
C39 C38 H38A 109.4 .
C37 C38 H38A 109.4 .
C39 C38 H38B 109.4 .
C37 C38 H38B 109.4 .
H38A C38 H38B 108.0 .
C38 C39 C40 111.5(9) .
C38 C39 H39A 109.3 .
C40 C39 H39A 109.3 .
C38 C39 H39B 109.3 .
C40 C39 H39B 109.3 .
H39A C39 H39B 108.0 .
O6 C40 C39 109.6(11) .
O6 C40 H40A 109.7 .
C39 C40 H40A 109.7 .
O6 C40 H40B 109.7 .
C39 C40 H40B 109.7 .
H40A C40 H40B 108.2 .
N1 C41 C42 117.3(9) .
N1 C41 H41A 108.0 .
C42 C41 H41A 108.0 .
N1 C41 H41B 108.0 .
C42 C41 H41B 108.0 .
H41A C41 H41B 107.2 .
C53 C42 C41 112.9(9) .
C53 C42 C43 109.7(16) .
C41 C42 C43 108.6(8) .
C53 C42 H42A 108.5 .
C41 C42 H42A 108.5 .
C43 C42 H42A 108.5 .
C44 C43 C42 109.4(9) .
C44 C43 H43A 109.8 .
C42 C43 H43A 109.8 .
C44 C43 H43B 109.8 .
C42 C43 H43B 109.8 .
H43A C43 H43B 108.2 .
C43 C44 C45 109.8(9) .
C43 C44 H44A 109.7 .
C45 C44 H44A 109.7 .
C43 C44 H44B 109.7 .
C45 C44 H44B 109.7 .
H44A C44 H44B 108.2 .
C46 C45 C44 110.4(9) .
C46 C45 H45A 109.6 .
C44 C45 H45A 109.6 .
C46 C45 H45B 109.6 .
C44 C45 H45B 109.6 .
H45A C45 H45B 108.1 .
C45 C46 C47 109.5(9) .
C45 C46 H46A 109.8 .
C47 C46 H46A 109.8 .
C45 C46 H46B 109.8 .
C47 C46 H46B 109.8 .
H46A C46 H46B 108.2 .
C48 C47 C46 109.7(10) .
C48 C47 H47A 109.7 .
C46 C47 H47A 109.7 .
C48 C47 H47B 109.7 .
C46 C47 H47B 109.7 .
H47A C47 H47B 108.2 .
C47 C48 C49 110.5(9) .
C47 C48 H48A 109.6 .
C49 C48 H48A 109.6 .
C47 C48 H48B 109.6 .
C49 C48 H48B 109.6 .
H48A C48 H48B 108.1 .
C50 C49 C48 110.2(9) .
C50 C49 H49A 109.6 .
C48 C49 H49A 109.6 .
C50 C49 H49B 109.6 .
C48 C49 H49B 109.6 .
H49A C49 H49B 108.1 .
C49 C50 C51 111.5(10) .
C49 C50 H50A 109.3 .
C51 C50 H50A 109.3 .
C49 C50 H50B 109.3 .
C51 C50 H50B 109.3 .
H50A C50 H50B 108.0 .
C50 C51 C52 108.6(10) .
C50 C51 H51A 110.0 .
C52 C51 H51A 110.0 .
C50 C51 H51B 110.0 .
C52 C51 H51B 110.0 .
H51A C51 H51B 108.3 .
C51 C52 H52A 109.5 .
C51 C52 H52B 109.5 .
H52A C52 H52B 109.5 .
C51 C52 H52C 109.5 .
H52A C52 H52C 109.5 .
H52B C52 H52C 109.5 .
C42 C53 C54 113.6(10) .
C42 C53 H53A 108.8 .
C54 C53 H53A 108.8 .
C42 C53 H53B 108.8 .
C54 C53 H53B 108.8 .
H53A C53 H53B 107.7 .
C55 C54 C53 108.7(10) .
C55 C54 H54A 109.9 .
C53 C54 H54A 109.9 .
C55 C54 H54B 109.9 .
C53 C54 H54B 109.9 .
H54A C54 H54B 108.3 .
C56 C55 C54 114.6(11) .
C56 C55 H55A 108.6 .
C54 C55 H55A 108.6 .
C56 C55 H55B 108.6 .
C54 C55 H55B 108.6 .
H55A C55 H55B 107.6 .
C55 C56 C57 112.0(11) .
C55 C56 H56A 109.2 .
C57 C56 H56A 109.2 .
C55 C56 H56B 109.2 .
C57 C56 H56B 109.2 .
H56A C56 H56B 107.9 .
C56 C57 C58 112.4(11) .
C56 C57 H57A 109.1 .
C58 C57 H57A 109.1 .
C56 C57 H57B 109.1 .
C58 C57 H57B 109.1 .
H57A C57 H57B 107.8 .
C57 C58 C59 109.4(10) .
C57 C58 H58A 109.8 .
C59 C58 H58A 109.8 .
C57 C58 H58B 109.8 .
C59 C58 H58B 109.8 .
H58A C58 H58B 108.2 .
C60 C59 C58 111.7(10) .
C60 C59 H59A 109.3 .
C58 C59 H59A 109.3 .
C60 C59 H59B 109.3 .
C58 C59 H59B 109.3 .
H59A C59 H59B 107.9 .
C59 C60 H60A 109.5 .
C59 C60 H60B 109.5 .
H60A C60 H60B 109.5 .
C59 C60 H60C 109.5 .
H60A C60 H60C 109.5 .
H60B C60 H60C 109.5 .
Cl3 C1S Cl1 110.6(8) .
Cl3 C1S Cl2 110.4(8) .
Cl1 C1S Cl2 110.2(8) .
Cl3 C1S H1S 108.5 .
Cl1 C1S H1S 108.5 .
Cl2 C1S H1S 108.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.213(13) .
O2 C2 1.212(14) .
O3 C14 1.390(12) .
O3 C25 1.446(8) .
O4 C18 1.367(14) .
O4 C33 1.433(8) .
O5 C20 1.406(15) .
O5 C32 1.441(9) .
O6 C24 1.346(18) .
O6 C40 1.460(9) .
N1 C2 1.374(15) .
N1 C1 1.422(15) .
N1 C41 1.452(13) .
C1 C3 1.480(15) .
C2 C4 1.506(16) .
C3 C5 1.400(15) .
C3 C6 1.405(14) .
C4 C7 1.390(15) .
C4 C6 1.411(15) .
C5 C8 1.382(14) .
C5 C13 1.496(15) .
C6 C9 1.414(14) .
C7 C10 1.379(15) .
C7 C19 1.515(17) .
C8 C11 1.401(14) .
C8 H8A 0.9500 .
C9 C12 1.409(14) .
C9 C11 1.427(14) .
C10 C12 1.386(15) .
C10 H10A 0.9500 .
C11 C12 1.462(14) 2_556
C13 C14 1.334(15) .
C13 C18 1.431(15) .
C14 C15 1.374(16) .
C15 C16 1.352(17) .
C15 H15A 0.9500 .
C16 C17 1.387(18) .
C16 H16A 0.9500 .
C17 C18 1.377(17) .
C17 H17A 0.9500 .
C19 C20 1.295(18) .
C19 C24 1.397(19) .
C20 C21 1.46(2) .
C21 C22 1.43(2) .
C21 H21A 0.9500 .
C22 C23 1.30(2) .
C22 H22A 0.9500 .
C23 C24 1.39(2) .
C23 H23A 0.9500 .
C25 C26 1.516(8) .
C25 H25A 0.9900 .
C25 H25B 0.9900 .
C26 C27 1.507(8) .
C26 H26A 0.9900 .
C26 H26B 0.9900 .
C27 C28 1.529(8) .
C27 H27A 0.9900 .
C27 H27B 0.9900 .
C28 C29 1.532(8) .
C28 H28A 0.9900 .
C28 H28B 0.9900 .
C29 C30 1.537(8) .
C29 H29A 0.9900 .
C29 H29B 0.9900 .
C30 C31 1.550(8) .
C30 H30A 0.9900 .
C30 H30B 0.9900 .
C31 C32 1.528(9) .
C31 H31A 0.9900 .
C31 H31B 0.9900 .
C32 H32A 0.9900 .
C32 H32B 0.9900 .
C33 C34 1.533(9) .
C33 H33A 0.9900 .
C33 H33B 0.9900 .
C34 C35 1.533(8) .
C34 H34A 0.9900 .
C34 H34B 0.9900 .
C35 C36 1.519(8) .
C35 H35A 0.9900 .
C35 H35B 0.9900 .
C36 C37 1.514(8) .
C36 H36A 0.9900 .
C36 H36B 0.9900 .
C37 C38 1.547(9) .
C37 H37A 0.9900 .
C37 H37B 0.9900 .
C38 C39 1.516(9) .
C38 H38A 0.9900 .
C38 H38B 0.9900 .
C39 C40 1.523(9) .
C39 H39A 0.9900 .
C39 H39B 0.9900 .
C40 H40A 0.9900 .
C40 H40B 0.9900 .
C41 C42 1.539(9) .
C41 H41A 0.9900 .
C41 H41B 0.9900 .
C42 C53 1.499(10) .
C42 C43 1.550(9) .
C42 H42A 1.0000 .
C43 C44 1.538(9) .
C43 H43A 0.9900 .
C43 H43B 0.9900 .
C44 C45 1.542(9) .
C44 H44A 0.9900 .
C44 H44B 0.9900 .
C45 C46 1.524(10) .
C45 H45A 0.9900 .
C45 H45B 0.9900 .
C46 C47 1.540(10) .
C46 H46A 0.9900 .
C46 H46B 0.9900 .
C47 C48 1.526(10) .
C47 H47A 0.9900 .
C47 H47B 0.9900 .
C48 C49 1.541(10) .
C48 H48A 0.9900 .
C48 H48B 0.9900 .
C49 C50 1.515(10) .
C49 H49A 0.9900 .
C49 H49B 0.9900 .
C50 C51 1.537(10) .
C50 H50A 0.9900 .
C50 H50B 0.9900 .
C51 C52 1.543(10) .
C51 H51A 0.9900 .
C51 H51B 0.9900 .
C52 H52A 0.9800 .
C52 H52B 0.9800 .
C52 H52C 0.9800 .
C53 C54 1.549(10) .
C53 H53A 0.9900 .
C53 H53B 0.9900 .
C54 C55 1.531(10) .
C54 H54A 0.9900 .
C54 H54B 0.9900 .
C55 C56 1.514(10) .
C55 H55A 0.9900 .
C55 H55B 0.9900 .
C56 C57 1.531(10) .
C56 H56A 0.9900 .
C56 H56B 0.9900 .
C57 C58 1.534(10) .
C57 H57A 0.9900 .
C57 H57B 0.9900 .
C58 C59 1.542(10) .
C58 H58A 0.9900 .
C58 H58B 0.9900 .
C59 C60 1.529(10) .
C59 H59A 0.9900 .
C59 H59B 0.9900 .
C60 H60A 0.9800 .
C60 H60B 0.9800 .
C60 H60C 0.9800 .
C1S Cl3 1.705(10) .
C1S Cl1 1.717(10) .
C1S Cl2 1.723(10) .
C1S H1S 1.0000 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168329733
