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#$Date: 2025-08-19 22:30:04 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301811 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/00/36/4003624.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_4003624
loop_
_publ_author_name
'Stolte, Matthias'
'Schembri, Tim'
'Süß, Jasmin'
'Schmidt, David'
'Krause, Ana-Maria'
'Vysotsky, Myroslav O.'
'Würthner, Frank'
_publ_section_title
;
 1-Mono- and 1,7-Disubstituted Perylene Bisimide Dyes with Voluminous
 Groups at Bay Positions: In Search for Highly Effective Solid-State
 Fluorescence Materials
;
_journal_name_full               'Chemistry of Materials'
_journal_paper_doi               10.1021/acs.chemmater.0c02115
_journal_year                    2020
_chemical_formula_moiety         'C102 H82 N2 O6, 2 (C H2 Cl2)'
_chemical_formula_sum            'C104 H86 Cl4 N2 O6'
_chemical_formula_weight         1601.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 104.3990(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   19.1734(7)
_cell_length_b                   11.1174(4)
_cell_length_c                   19.4307(8)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.58
_cell_measurement_theta_min      2.19
_cell_volume                     4011.7(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            49788
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.052
_diffrn_reflns_theta_min         1.335
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker-SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       plate
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.154
_refine_diff_density_min         -1.056
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         7924
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0554
_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)+(0.0695P)²+5.5694P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1538
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5999
_reflns_number_total             7924
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cm0c02115_si_005.cif
_cod_data_source_block           JSBA05_fertig
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4003624
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.32581(10) 0.36034(17) 0.20175(9) 0.0284(4) Uani 1 1 d . . . . .
O2 O 0.53152(10) 0.56019(16) 0.19668(9) 0.0255(4) Uani 1 1 d . . . . .
O3 O 0.66038(8) 0.63637(14) 0.44941(8) 0.0143(3) Uani 1 1 d . . . . .
N1 N 0.43164(11) 0.45022(18) 0.19773(10) 0.0188(4) Uani 1 1 d . . . . .
C1 C 0.49364(13) 0.5142(2) 0.23113(12) 0.0177(5) Uani 1 1 d . . . . .
C2 C 0.51244(12) 0.52004(19) 0.30961(11) 0.0135(4) Uani 1 1 d . . . . .
C3 C 0.57613(12) 0.57212(19) 0.34343(11) 0.0144(5) Uani 1 1 d . . . . .
H3 H 0.6077 0.6010 0.3164 0.017 Uiso 1 1 calc R U . . .
C4 C 0.59563(11) 0.58351(19) 0.41739(11) 0.0125(4) Uani 1 1 d . . . . .
C5 C 0.55094(11) 0.54123(18) 0.46036(11) 0.0116(4) Uani 1 1 d . . . . .
C6 C 0.48334(11) 0.48889(18) 0.42433(11) 0.0110(4) Uani 1 1 d . . . . .
C7 C 0.43117(11) 0.44943(18) 0.46165(11) 0.0115(4) Uani 1 1 d . . . . .
C8 C 0.36527(12) 0.4062(2) 0.42181(12) 0.0171(5) Uani 1 1 d . . . . .
H8 H 0.3296 0.3845 0.4459 0.021 Uiso 1 1 calc R U . . .
C9 C 0.34933(12) 0.3936(2) 0.34820(12) 0.0184(5) Uani 1 1 d . . . . .
H9 H 0.3041 0.3617 0.3233 0.022 Uiso 1 1 calc R U . . .
C10 C 0.39869(12) 0.42693(19) 0.31173(11) 0.0144(5) Uani 1 1 d . . . . .
C11 C 0.38143(13) 0.4093(2) 0.23383(12) 0.0193(5) Uani 1 1 d . . . . .
C12 C 0.46492(12) 0.47723(18) 0.34883(11) 0.0124(4) Uani 1 1 d . . . . .
C21A C 0.4105(3) 0.4191(5) 0.1195(4) 0.0170(13) Uani 0.604(3) 1 d D . P A 1
H21A H 0.3664 0.3677 0.1113 0.020 Uiso 0.604(3) 1 calc R U P A 1
C22A C 0.4689(3) 0.3450(4) 0.0980(2) 0.0237(8) Uani 0.604(3) 1 d D . P A 1
H22A H 0.4789 0.2712 0.1273 0.028 Uiso 0.604(3) 1 calc R U P A 1
H22B H 0.5140 0.3923 0.1062 0.028 Uiso 0.604(3) 1 calc R U P A 1
C23A C 0.4435(4) 0.3110(8) 0.0190(4) 0.0246(17) Uani 0.604(3) 1 d D . P A 1
H23A H 0.4832 0.2704 0.0040 0.029 Uiso 0.604(3) 1 calc R U P A 1
H23B H 0.4028 0.2538 0.0125 0.029 Uiso 0.604(3) 1 calc R U P A 1
C24A C 0.4198(3) 0.4207(4) -0.0273(2) 0.0310(8) Uani 0.604(3) 1 d D . P A 1
H24A H 0.4623 0.4719 -0.0263 0.037 Uiso 0.604(3) 1 calc R U P A 1
H24B H 0.3998 0.3943 -0.0770 0.037 Uiso 0.604(3) 1 calc R U P A 1
C25A C 0.3637(11) 0.4942(12) -0.0035(5) 0.0322(11) Uani 0.604(3) 1 d D . P A 1
H25A H 0.3190 0.4464 -0.0097 0.039 Uiso 0.604(3) 1 calc R U P A 1
H25B H 0.3523 0.5671 -0.0335 0.039 Uiso 0.604(3) 1 calc R U P A 1
C26A C 0.3905(3) 0.5314(6) 0.0746(4) 0.0280(15) Uani 0.604(3) 1 d D . P A 1
H26A H 0.4329 0.5846 0.0807 0.034 Uiso 0.604(3) 1 calc R U P A 1
H26B H 0.3522 0.5760 0.0898 0.034 Uiso 0.604(3) 1 calc R U P A 1
C21B C 0.4271(6) 0.4476(9) 0.1192(7) 0.0170(13) Uani 0.396(3) 1 d D . P A 2
H21B H 0.4715 0.4863 0.1113 0.020 Uiso 0.396(3) 1 calc R U P A 2
C22B C 0.4263(4) 0.3170(6) 0.0959(3) 0.0237(8) Uani 0.396(3) 1 d D . P A 2
H22C H 0.3848 0.2749 0.1068 0.028 Uiso 0.396(3) 1 calc R U P A 2
H22D H 0.4709 0.2766 0.1223 0.028 Uiso 0.396(3) 1 calc R U P A 2
C23B C 0.4207(7) 0.3101(13) 0.0162(6) 0.0246(17) Uani 0.396(3) 1 d D . P A 2
H23C H 0.4663 0.3391 0.0068 0.029 Uiso 0.396(3) 1 calc R U P A 2
H23D H 0.4140 0.2252 0.0006 0.029 Uiso 0.396(3) 1 calc R U P A 2
C24B C 0.3593(4) 0.3839(6) -0.0264(3) 0.0310(8) Uani 0.396(3) 1 d D . P A 2
H24C H 0.3133 0.3465 -0.0234 0.037 Uiso 0.396(3) 1 calc R U P A 2
H24D H 0.3611 0.3832 -0.0769 0.037 Uiso 0.396(3) 1 calc R U P A 2
C25B C 0.3609(18) 0.5127(19) -0.0012(8) 0.0322(11) Uani 0.396(3) 1 d D . P A 2
H25C H 0.3177 0.5555 -0.0287 0.039 Uiso 0.396(3) 1 calc R U P A 2
H25D H 0.4039 0.5536 -0.0096 0.039 Uiso 0.396(3) 1 calc R U P A 2
C26B C 0.3630(5) 0.5178(11) 0.0784(6) 0.0280(15) Uani 0.396(3) 1 d D . P A 2
H26C H 0.3667 0.6024 0.0948 0.034 Uiso 0.396(3) 1 calc R U P A 2
H26D H 0.3182 0.4830 0.0865 0.034 Uiso 0.396(3) 1 calc R U P A 2
C31 C 0.69808(11) 0.6999(2) 0.40722(11) 0.0134(4) Uani 1 1 d . . . . .
C32 C 0.67571(12) 0.8158(2) 0.38426(11) 0.0146(5) Uani 1 1 d . . . . .
C33 C 0.71640(12) 0.8768(2) 0.34521(12) 0.0161(5) Uani 1 1 d . . . . .
H33 H 0.7019 0.9552 0.3279 0.019 Uiso 1 1 calc R U . . .
C34 C 0.77750(12) 0.8267(2) 0.33088(11) 0.0158(5) Uani 1 1 d . . . . .
C35 C 0.79868(12) 0.7120(2) 0.35639(11) 0.0160(5) Uani 1 1 d . . . . .
H35 H 0.8404 0.6771 0.3467 0.019 Uiso 1 1 calc R U . . .
C36 C 0.76001(12) 0.6471(2) 0.39591(11) 0.0150(5) Uani 1 1 d . . . . .
C37 C 0.82216(13) 0.8986(2) 0.29174(13) 0.0224(5) Uani 1 1 d . . . . .
H37A H 0.8397 0.8456 0.2594 0.034 Uiso 1 1 calc R U . . .
H37B H 0.8632 0.9344 0.3260 0.034 Uiso 1 1 calc R U . . .
H37C H 0.7926 0.9625 0.2644 0.034 Uiso 1 1 calc R U . . .
C38 C 0.61012(12) 0.8712(2) 0.40334(12) 0.0170(5) Uani 1 1 d . . . . .
H38 H 0.5689 0.8152 0.3850 0.020 Uiso 1 1 calc R U . . .
C39 C 0.78384(12) 0.5252(2) 0.42975(12) 0.0179(5) Uani 1 1 d . . . . .
H39 H 0.7411 0.4708 0.4165 0.021 Uiso 1 1 calc R U . . .
C41 C 0.58957(12) 0.9916(2) 0.36587(13) 0.0175(5) Uani 1 1 d . . . . .
C42 C 0.62263(15) 1.0982(2) 0.39328(15) 0.0295(6) Uani 1 1 d . . . . .
H42 H 0.6580 1.0974 0.4373 0.035 Uiso 1 1 calc R U . . .
C43 C 0.60471(16) 1.2057(2) 0.35733(16) 0.0330(6) Uani 1 1 d . . . . .
H43 H 0.6273 1.2783 0.3770 0.040 Uiso 1 1 calc R U . . .
C44 C 0.55384(14) 1.2076(2) 0.29278(14) 0.0255(6) Uani 1 1 d . . . . .
H44 H 0.5412 1.2815 0.2683 0.031 Uiso 1 1 calc R U . . .
C45 C 0.52167(14) 1.1022(2) 0.26422(13) 0.0239(5) Uani 1 1 d . . . . .
H45 H 0.4872 1.1030 0.2196 0.029 Uiso 1 1 calc R U . . .
C46 C 0.53968(13) 0.9944(2) 0.30084(13) 0.0201(5) Uani 1 1 d . . . . .
H46 H 0.5174 0.9218 0.2809 0.024 Uiso 1 1 calc R U . . .
C51 C 0.61905(13) 0.8813(2) 0.48345(13) 0.0217(5) Uani 1 1 d . . . . .
C52 C 0.55822(16) 0.8726(3) 0.50970(15) 0.0320(6) Uani 1 1 d . . . . .
H52 H 0.5125 0.8590 0.4779 0.038 Uiso 1 1 calc R U . . .
C53 C 0.56339(19) 0.8833(3) 0.58135(17) 0.0430(8) Uani 1 1 d . . . . .
H53 H 0.5215 0.8758 0.5988 0.052 Uiso 1 1 calc R U . . .
C54 C 0.6293(2) 0.9050(3) 0.62801(16) 0.0460(9) Uani 1 1 d . . . . .
H54 H 0.6325 0.9139 0.6773 0.055 Uiso 1 1 calc R U . . .
C55 C 0.69055(19) 0.9138(3) 0.60284(15) 0.0408(7) Uani 1 1 d . . . . .
H55 H 0.7360 0.9284 0.6349 0.049 Uiso 1 1 calc R U . . .
C56 C 0.68546(15) 0.9012(2) 0.53054(14) 0.0291(6) Uani 1 1 d . . . . .
H56 H 0.7276 0.9061 0.5133 0.035 Uiso 1 1 calc R U . . .
C61 C 0.84384(13) 0.4653(2) 0.40300(12) 0.0188(5) Uani 1 1 d . . . . .
C62 C 0.82883(14) 0.3657(2) 0.35887(12) 0.0229(5) Uani 1 1 d . . . . .
H62 H 0.7809 0.3363 0.3445 0.028 Uiso 1 1 calc R U . . .
C63 C 0.88315(15) 0.3083(2) 0.33548(13) 0.0286(6) Uani 1 1 d . . . . .
H63 H 0.8721 0.2406 0.3049 0.034 Uiso 1 1 calc R U . . .
C64 C 0.95306(15) 0.3496(3) 0.35653(13) 0.0300(6) Uani 1 1 d . . . . .
H64 H 0.9904 0.3096 0.3413 0.036 Uiso 1 1 calc R U . . .
C65 C 0.96856(14) 0.4497(3) 0.40001(13) 0.0269(6) Uani 1 1 d . . . . .
H65 H 1.0165 0.4792 0.4139 0.032 Uiso 1 1 calc R U . . .
C66 C 0.91462(13) 0.5070(2) 0.42348(13) 0.0221(5) Uani 1 1 d . . . . .
H66 H 0.9259 0.5751 0.4537 0.027 Uiso 1 1 calc R U . . .
C71 C 0.80495(12) 0.5327(2) 0.51115(13) 0.0188(5) Uani 1 1 d . . . . .
C72 C 0.80179(14) 0.4287(2) 0.55013(14) 0.0255(6) Uani 1 1 d . . . . .
H72 H 0.7855 0.3558 0.5259 0.031 Uiso 1 1 calc R U . . .
C73 C 0.82219(15) 0.4299(3) 0.62422(14) 0.0313(6) Uani 1 1 d . . . . .
H73 H 0.8207 0.3579 0.6501 0.038 Uiso 1 1 calc R U . . .
C74 C 0.84453(14) 0.5361(3) 0.65983(14) 0.0304(6) Uani 1 1 d . . . . .
H74 H 0.8577 0.5378 0.7103 0.036 Uiso 1 1 calc R U . . .
C75 C 0.84759(14) 0.6397(3) 0.62154(14) 0.0279(6) Uani 1 1 d . . . . .
H75 H 0.8630 0.7128 0.6459 0.033 Uiso 1 1 calc R U . . .
C76 C 0.82840(13) 0.6380(2) 0.54809(13) 0.0217(5) Uani 1 1 d . . . . .
H76 H 0.8313 0.7099 0.5225 0.026 Uiso 1 1 calc R U . . .
Cl1A Cl 0.40033(5) 0.76647(8) 0.31467(4) 0.0481(3) Uani 0.8981(12) 1 d G . P B 1
Cl2A Cl 0.36394(5) 0.75192(8) 0.45243(4) 0.0482(2) Uani 0.8981(12) 1 d G . P B 1
C81A C 0.33322(13) 0.7357(7) 0.35970(5) 0.0417(8) Uani 0.8981(12) 1 d G . P B 1
H81A H 0.3157 0.6434 0.3484 0.050 Uiso 0.8981(12) 1 d G U P B 1
H82A H 0.2893 0.7985 0.3410 0.050 Uiso 0.8981(12) 1 d G U P B 1
Cl1B Cl 0.3047(4) 0.6846(7) 0.2618(4) 0.0481(3) Uani 0.1019(12) 1 d G . P B 2
Cl2B Cl 0.4155(4) 0.7859(7) 0.3796(4) 0.0482(2) Uani 0.1019(12) 1 d G . P B 2
C81B C 0.3271(14) 0.730(6) 0.3514(12) 0.0417(8) Uani 0.1019(12) 1 d G . P B 2
H81B H 0.3225 0.6523 0.3838 0.050 Uiso 0.1019(12) 1 d G U P B 2
H82B H 0.2903 0.8009 0.3575 0.050 Uiso 0.1019(12) 1 d G U P B 2
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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O3 C31 119.15(16) . . ?
C1 N1 C11 122.92(19) . . ?
C1 N1 C21B 108.0(4) . . ?
C11 N1 C21B 128.8(4) . . ?
C1 N1 C21A 124.6(3) . . ?
C11 N1 C21A 112.5(3) . . ?
O2 C1 N1 120.9(2) . . ?
O2 C1 C2 121.6(2) . . ?
N1 C1 C2 117.51(19) . . ?
C3 C2 C12 120.3(2) . . ?
C3 C2 C1 118.4(2) . . ?
C12 C2 C1 121.3(2) . . ?
C2 C3 C4 120.8(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
O3 C4 C3 118.98(18) . . ?
O3 C4 C5 119.06(19) . . ?
C3 C4 C5 122.0(2) . . ?
C4 C5 C6 116.91(19) . . ?
C4 C5 C7 124.3(2) . 3_666 ?
C6 C5 C7 118.81(19) . 3_666 ?
C12 C6 C5 120.07(19) . . ?
C12 C6 C7 117.65(19) . . ?
C5 C6 C7 122.25(19) . . ?
C8 C7 C6 118.18(19) . . ?
C8 C7 C5 122.92(19) . 3_666 ?
C6 C7 C5 118.88(19) . 3_666 ?
C7 C8 C9 122.8(2) . . ?
C7 C8 H8 118.6 . . ?
C9 C8 H8 118.6 . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C12 119.6(2) . . ?
C9 C10 C11 119.1(2) . . ?
C12 C10 C11 121.3(2) . . ?
O1 C11 N1 120.7(2) . . ?
O1 C11 C10 121.7(2) . . ?
N1 C11 C10 117.5(2) . . ?
C2 C12 C10 118.6(2) . . ?
C2 C12 C6 119.9(2) . . ?
C10 C12 C6 121.51(19) . . ?
N1 C21A C26A 110.9(5) . . ?
N1 C21A C22A 111.4(5) . . ?
C26A C21A C22A 112.6(5) . . ?
N1 C21A H21A 107.2 . . ?
C26A C21A H21A 107.2 . . ?
C22A C21A H21A 107.2 . . ?
C21A C22A C23A 109.4(5) . . ?
C21A C22A H22A 109.8 . . ?
C23A C22A H22A 109.8 . . ?
C21A C22A H22B 109.8 . . ?
C23A C22A H22B 109.8 . . ?
H22A C22A H22B 108.2 . . ?
C24A C23A C22A 111.7(6) . . ?
C24A C23A H23A 109.3 . . ?
C22A C23A H23A 109.3 . . ?
C24A C23A H23B 109.3 . . ?
C22A C23A H23B 109.3 . . ?
H23A C23A H23B 107.9 . . ?
C25A C24A C23A 112.5(6) . . ?
C25A C24A H24A 109.1 . . ?
C23A C24A H24A 109.1 . . ?
C25A C24A H24B 109.1 . . ?
C23A C24A H24B 109.1 . . ?
H24A C24A H24B 107.8 . . ?
C24A C25A C26A 111.2(10) . . ?
C24A C25A H25A 109.4 . . ?
C26A C25A H25A 109.4 . . ?
C24A C25A H25B 109.4 . . ?
C26A C25A H25B 109.4 . . ?
H25A C25A H25B 108.0 . . ?
C21A C26A C25A 108.8(7) . . ?
C21A C26A H26A 109.9 . . ?
C25A C26A H26A 109.9 . . ?
C21A C26A H26B 109.9 . . ?
C25A C26A H26B 109.9 . . ?
H26A C26A H26B 108.3 . . ?
C26B C21B N1 111.0(9) . . ?
C26B C21B C22B 113.1(9) . . ?
N1 C21B C22B 108.3(7) . . ?
C26B C21B H21B 108.1 . . ?
N1 C21B H21B 108.1 . . ?
C22B C21B H21B 108.1 . . ?
C21B C22B C23B 110.1(8) . . ?
C21B C22B H22C 109.6 . . ?
C23B C22B H22C 109.6 . . ?
C21B C22B H22D 109.6 . . ?
C23B C22B H22D 109.6 . . ?
H22C C22B H22D 108.2 . . ?
C24B C23B C22B 112.3(8) . . ?
C24B C23B H23C 109.2 . . ?
C22B C23B H23C 109.2 . . ?
C24B C23B H23D 109.2 . . ?
C22B C23B H23D 109.2 . . ?
H23C C23B H23D 107.9 . . ?
C23B C24B C25B 112.8(11) . . ?
C23B C24B H24C 109.0 . . ?
C25B C24B H24C 109.0 . . ?
C23B C24B H24D 109.0 . . ?
C25B C24B H24D 109.0 . . ?
H24C C24B H24D 107.8 . . ?
C24B C25B C26B 110.7(15) . . ?
C24B C25B H25C 109.5 . . ?
C26B C25B H25C 109.5 . . ?
C24B C25B H25D 109.5 . . ?
C26B C25B H25D 109.5 . . ?
H25C C25B H25D 108.1 . . ?
C21B C26B C25B 109.0(11) . . ?
C21B C26B H26C 109.9 . . ?
C25B C26B H26C 109.9 . . ?
C21B C26B H26D 109.9 . . ?
C25B C26B H26D 109.9 . . ?
H26C C26B H26D 108.3 . . ?
C36 C31 C32 123.1(2) . . ?
C36 C31 O3 117.49(19) . . ?
C32 C31 O3 119.15(19) . . ?
C33 C32 C31 117.0(2) . . ?
C33 C32 C38 122.9(2) . . ?
C31 C32 C38 120.06(19) . . ?
C34 C33 C32 122.0(2) . . ?
C34 C33 H33 119.0 . . ?
C32 C33 H33 119.0 . . ?
C33 C34 C35 118.9(2) . . ?
C33 C34 C37 120.1(2) . . ?
C35 C34 C37 120.9(2) . . ?
C34 C35 C36 121.5(2) . . ?
C34 C35 H35 119.2 . . ?
C36 C35 H35 119.2 . . ?
C31 C36 C35 117.4(2) . . ?
C31 C36 C39 118.89(19) . . ?
C35 C36 C39 123.6(2) . . ?
C34 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C34 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C32 C38 C51 112.76(18) . . ?
C32 C38 C41 111.59(18) . . ?
C51 C38 C41 111.80(19) . . ?
C32 C38 H38 106.7 . . ?
C51 C38 H38 106.7 . . ?
C41 C38 H38 106.7 . . ?
C36 C39 C61 114.24(19) . . ?
C36 C39 C71 111.73(19) . . ?
C61 C39 C71 110.27(18) . . ?
C36 C39 H39 106.7 . . ?
C61 C39 H39 106.7 . . ?
C71 C39 H39 106.7 . . ?
C46 C41 C42 118.6(2) . . ?
C46 C41 C38 119.5(2) . . ?
C42 C41 C38 121.8(2) . . ?
C43 C42 C41 120.8(2) . . ?
C43 C42 H42 119.6 . . ?
C41 C42 H42 119.6 . . ?
C42 C43 C44 120.1(2) . . ?
C42 C43 H43 120.0 . . ?
C44 C43 H43 120.0 . . ?
C45 C44 C43 119.8(2) . . ?
C45 C44 H44 120.1 . . ?
C43 C44 H44 120.1 . . ?
C44 C45 C46 119.9(2) . . ?
C44 C45 H45 120.1 . . ?
C46 C45 H45 120.1 . . ?
C41 C46 C45 120.9(2) . . ?
C41 C46 H46 119.6 . . ?
C45 C46 H46 119.6 . . ?
C52 C51 C56 119.1(2) . . ?
C52 C51 C38 118.5(2) . . ?
C56 C51 C38 122.4(2) . . ?
C53 C52 C51 120.7(3) . . ?
C53 C52 H52 119.7 . . ?
C51 C52 H52 119.7 . . ?
C52 C53 C54 120.2(3) . . ?
C52 C53 H53 119.9 . . ?
C54 C53 H53 119.9 . . ?
C53 C54 C55 119.9(3) . . ?
C53 C54 H54 120.0 . . ?
C55 C54 H54 120.0 . . ?
C54 C55 C56 119.8(3) . . ?
C54 C55 H55 120.1 . . ?
C56 C55 H55 120.1 . . ?
C51 C56 C55 120.3(3) . . ?
C51 C56 H56 119.9 . . ?
C55 C56 H56 119.9 . . ?
C62 C61 C66 118.6(2) . . ?
C62 C61 C39 120.0(2) . . ?
C66 C61 C39 121.3(2) . . ?
C61 C62 C63 120.8(2) . . ?
C61 C62 H62 119.6 . . ?
C63 C62 H62 119.6 . . ?
C64 C63 C62 120.2(3) . . ?
C64 C63 H63 119.9 . . ?
C62 C63 H63 119.9 . . ?
C63 C64 C65 119.6(2) . . ?
C63 C64 H64 120.2 . . ?
C65 C64 H64 120.2 . . ?
C64 C65 C66 120.4(3) . . ?
C64 C65 H65 119.8 . . ?
C66 C65 H65 119.8 . . ?
C65 C66 C61 120.4(2) . . ?
C65 C66 H66 119.8 . . ?
C61 C66 H66 119.8 . . ?
C76 C71 C72 118.1(2) . . ?
C76 C71 C39 123.2(2) . . ?
C72 C71 C39 118.7(2) . . ?
C71 C72 C73 121.0(3) . . ?
C71 C72 H72 119.5 . . ?
C73 C72 H72 119.5 . . ?
C74 C73 C72 119.9(2) . . ?
C74 C73 H73 120.1 . . ?
C72 C73 H73 120.1 . . ?
C75 C74 C73 119.5(2) . . ?
C75 C74 H74 120.3 . . ?
C73 C74 H74 120.3 . . ?
C74 C75 C76 120.6(3) . . ?
C74 C75 H75 119.7 . . ?
C76 C75 H75 119.7 . . ?
C75 C76 C71 120.9(2) . . ?
C75 C76 H76 119.5 . . ?
C71 C76 H76 119.5 . . ?
Cl2A C81A Cl1A 112.9 . . ?
Cl2A C81A H81A 108.1 . . ?
Cl1A C81A H81A 108.1 . . ?
Cl2A C81A H82A 108.1 . . ?
Cl1A C81A H82A 108.1 . . ?
H81A C81A H82A 111.4 . . ?
Cl1B C81B Cl2B 112.9 . . ?
Cl1B C81B H81B 108.1 . . ?
Cl2B C81B H81B 108.1 . . ?
Cl1B C81B H82B 108.1 . . ?
Cl2B C81B H82B 108.1 . . ?
H81B C81B H82B 111.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.221(3) . ?
O2 C1 1.216(3) . ?
O3 C4 1.375(3) . ?
O3 C31 1.410(2) . ?
N1 C1 1.399(3) . ?
N1 C11 1.401(3) . ?
N1 C21B 1.507(13) . ?
N1 C21A 1.513(8) . ?
C1 C2 1.478(3) . ?
C2 C3 1.364(3) . ?
C2 C12 1.408(3) . ?
C3 C4 1.398(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.417(3) . ?
C5 C6 1.434(3) . ?
C5 C7 1.472(3) 3_666 ?
C6 C12 1.427(3) . ?
C6 C7 1.442(3) . ?
C7 C8 1.393(3) . ?
C7 C5 1.472(3) 3_666 ?
C8 C9 1.393(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.367(3) . ?
C9 H9 0.9500 . ?
C10 C12 1.411(3) . ?
C10 C11 1.480(3) . ?
C21A C26A 1.516(7) . ?
C21A C22A 1.531(7) . ?
C21A H21A 1.0000 . ?
C22A C23A 1.538(7) . ?
C22A H22A 0.9900 . ?
C22A H22B 0.9900 . ?
C23A C24A 1.517(9) . ?
C23A H23A 0.9900 . ?
C23A H23B 0.9900 . ?
C24A C25A 1.511(13) . ?
C24A H24A 0.9900 . ?
C24A H24B 0.9900 . ?
C25A C26A 1.533(9) . ?
C25A H25A 0.9900 . ?
C25A H25B 0.9900 . ?
C26A H26A 0.9900 . ?
C26A H26B 0.9900 . ?
C21B C26B 1.504(11) . ?
C21B C22B 1.520(11) . ?
C21B H21B 1.0000 . ?
C22B C23B 1.528(11) . ?
C22B H22C 0.9900 . ?
C22B H22D 0.9900 . ?
C23B C24B 1.503(11) . ?
C23B H23C 0.9900 . ?
C23B H23D 0.9900 . ?
C24B C25B 1.511(18) . ?
C24B H24C 0.9900 . ?
C24B H24D 0.9900 . ?
C25B C26B 1.538(14) . ?
C25B H25C 0.9900 . ?
C25B H25D 0.9900 . ?
C26B H26C 0.9900 . ?
C26B H26D 0.9900 . ?
C31 C36 1.390(3) . ?
C31 C32 1.396(3) . ?
C32 C33 1.392(3) . ?
C32 C38 1.526(3) . ?
C33 C34 1.387(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.392(3) . ?
C34 C37 1.508(3) . ?
C35 C36 1.394(3) . ?
C35 H35 0.9500 . ?
C36 C39 1.525(3) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 C51 1.527(3) . ?
C38 C41 1.528(3) . ?
C38 H38 1.0000 . ?
C39 C61 1.528(3) . ?
C39 C71 1.534(3) . ?
C39 H39 1.0000 . ?
C41 C46 1.383(3) . ?
C41 C42 1.386(3) . ?
C42 C43 1.384(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.384(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.375(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.393(3) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C51 C52 1.388(4) . ?
C51 C56 1.388(4) . ?
C52 C53 1.376(4) . ?
C52 H52 0.9500 . ?
C53 C54 1.381(5) . ?
C53 H53 0.9500 . ?
C54 C55 1.384(5) . ?
C54 H54 0.9500 . ?
C55 C56 1.391(4) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
C61 C62 1.387(3) . ?
C61 C66 1.395(3) . ?
C62 C63 1.391(4) . ?
C62 H62 0.9500 . ?
C63 C64 1.379(4) . ?
C63 H63 0.9500 . ?
C64 C65 1.384(4) . ?
C64 H64 0.9500 . ?
C65 C66 1.385(3) . ?
C65 H65 0.9500 . ?
C66 H66 0.9500 . ?
C71 C76 1.388(4) . ?
C71 C72 1.392(3) . ?
C72 C73 1.395(4) . ?
C72 H72 0.9500 . ?
C73 C74 1.381(4) . ?
C73 H73 0.9500 . ?
C74 C75 1.380(4) . ?
C74 H74 0.9500 . ?
C75 C76 1.383(4) . ?
C75 H75 0.9500 . ?
C76 H76 0.9500 . ?
Cl1A C81A 1.7602 . ?
Cl2A C81A 1.7601 . ?
C81A H81A 1.0846 . ?
C81A H82A 1.0845 . ?
Cl1B C81B 1.7601 . ?
Cl2B C81B 1.7601 . ?
C81B H81B 1.0847 . ?
C81B H82B 1.0845 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 C1 O2 -171.4(2) . . . . ?
C21B N1 C1 O2 2.8(5) . . . . ?
C21A N1 C1 O2 7.6(4) . . . . ?
C11 N1 C1 C2 10.6(3) . . . . ?
C21B N1 C1 C2 -175.2(5) . . . . ?
C21A N1 C1 C2 -170.4(3) . . . . ?
O2 C1 C2 C3 -4.0(3) . . . . ?
N1 C1 C2 C3 173.89(19) . . . . ?
O2 C1 C2 C12 173.6(2) . . . . ?
N1 C1 C2 C12 -8.5(3) . . . . ?
C12 C2 C3 C4 0.3(3) . . . . ?
C1 C2 C3 C4 177.96(19) . . . . ?
C31 O3 C4 C3 13.3(3) . . . . ?
C31 O3 C4 C5 -167.27(18) . . . . ?
C2 C3 C4 O3 179.88(19) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
O3 C4 C5 C6 178.84(17) . . . . ?
C3 C4 C5 C6 -1.7(3) . . . . ?
O3 C4 C5 C7 0.4(3) . . . 3_666 ?
C3 C4 C5 C7 179.84(19) . . . 3_666 ?
C4 C5 C6 C12 2.3(3) . . . . ?
C7 C5 C6 C12 -179.20(18) 3_666 . . . ?
C4 C5 C6 C7 -176.05(19) . . . . ?
C7 C5 C6 C7 2.5(3) 3_666 . . . ?
C12 C6 C7 C8 -2.1(3) . . . . ?
C5 C6 C7 C8 176.3(2) . . . . ?
C12 C6 C7 C5 179.15(18) . . . 3_666 ?
C5 C6 C7 C5 -2.5(3) . . . 3_666 ?
C6 C7 C8 C9 3.6(3) . . . . ?
C5 C7 C8 C9 -177.7(2) 3_666 . . . ?
C7 C8 C9 C10 -1.7(4) . . . . ?
C8 C9 C10 C12 -1.8(3) . . . . ?
C8 C9 C10 C11 178.2(2) . . . . ?
C1 N1 C11 O1 175.4(2) . . . . ?
C21B N1 C11 O1 2.5(6) . . . . ?
C21A N1 C11 O1 -3.7(4) . . . . ?
C1 N1 C11 C10 -5.0(3) . . . . ?
C21B N1 C11 C10 -177.9(5) . . . . ?
C21A N1 C11 C10 175.9(3) . . . . ?
C9 C10 C11 O1 -3.7(3) . . . . ?
C12 C10 C11 O1 176.3(2) . . . . ?
C9 C10 C11 N1 176.7(2) . . . . ?
C12 C10 C11 N1 -3.3(3) . . . . ?
C3 C2 C12 C10 178.3(2) . . . . ?
C1 C2 C12 C10 0.7(3) . . . . ?
C3 C2 C12 C6 0.3(3) . . . . ?
C1 C2 C12 C6 -177.30(19) . . . . ?
C9 C10 C12 C2 -174.8(2) . . . . ?
C11 C10 C12 C2 5.2(3) . . . . ?
C9 C10 C12 C6 3.1(3) . . . . ?
C11 C10 C12 C6 -176.80(19) . . . . ?
C5 C6 C12 C2 -1.6(3) . . . . ?
C7 C6 C12 C2 176.78(19) . . . . ?
C5 C6 C12 C10 -179.56(19) . . . . ?
C7 C6 C12 C10 -1.2(3) . . . . ?
C1 N1 C21A C26A -67.9(5) . . . . ?
C11 N1 C21A C26A 111.2(4) . . . . ?
C1 N1 C21A C22A 58.4(5) . . . . ?
C11 N1 C21A C22A -122.6(3) . . . . ?
N1 C21A C22A C23A 177.5(5) . . . . ?
C26A C21A C22A C23A -57.2(7) . . . . ?
C21A C22A C23A C24A 53.2(6) . . . . ?
C22A C23A C24A C25A -53.8(10) . . . . ?
C23A C24A C25A C26A 55.6(15) . . . . ?
N1 C21A C26A C25A -175.5(9) . . . . ?
C22A C21A C26A C25A 58.9(11) . . . . ?
C24A C25A C26A C21A -56.9(15) . . . . ?
C1 N1 C21B C26B -113.8(7) . . . . ?
C11 N1 C21B C26B 59.9(9) . . . . ?
C1 N1 C21B C22B 121.5(6) . . . . ?
C11 N1 C21B C22B -64.8(9) . . . . ?
C26B C21B C22B C23B 55.8(12) . . . . ?
N1 C21B C22B C23B 179.3(7) . . . . ?
C21B C22B C23B C24B -51.7(13) . . . . ?
C22B C23B C24B C25B 53.0(17) . . . . ?
C23B C24B C25B C26B -55(2) . . . . ?
N1 C21B C26B C25B 179.8(14) . . . . ?
C22B C21B C26B C25B -58.2(17) . . . . ?
C24B C25B C26B C21B 57(2) . . . . ?
C4 O3 C31 C36 -107.6(2) . . . . ?
C4 O3 C31 C32 78.0(3) . . . . ?
C36 C31 C32 C33 3.3(3) . . . . ?
O3 C31 C32 C33 177.43(19) . . . . ?
C36 C31 C32 C38 -175.6(2) . . . . ?
O3 C31 C32 C38 -1.5(3) . . . . ?
C31 C32 C33 C34 -1.5(3) . . . . ?
C38 C32 C33 C34 177.4(2) . . . . ?
C32 C33 C34 C35 0.0(3) . . . . ?
C32 C33 C34 C37 -176.7(2) . . . . ?
C33 C34 C35 C36 -0.1(3) . . . . ?
C37 C34 C35 C36 176.5(2) . . . . ?
C32 C31 C36 C35 -3.5(3) . . . . ?
O3 C31 C36 C35 -177.68(19) . . . . ?
C32 C31 C36 C39 173.7(2) . . . . ?
O3 C31 C36 C39 -0.4(3) . . . . ?
C34 C35 C36 C31 1.8(3) . . . . ?
C34 C35 C36 C39 -175.3(2) . . . . ?
C33 C32 C38 C51 -118.8(2) . . . . ?
C31 C32 C38 C51 60.0(3) . . . . ?
C33 C32 C38 C41 8.0(3) . . . . ?
C31 C32 C38 C41 -173.2(2) . . . . ?
C31 C36 C39 C61 169.3(2) . . . . ?
C35 C36 C39 C61 -13.7(3) . . . . ?
C31 C36 C39 C71 -64.7(3) . . . . ?
C35 C36 C39 C71 112.4(2) . . . . ?
C32 C38 C41 C46 92.2(2) . . . . ?
C51 C38 C41 C46 -140.5(2) . . . . ?
C32 C38 C41 C42 -84.1(3) . . . . ?
C51 C38 C41 C42 43.2(3) . . . . ?
C46 C41 C42 C43 1.7(4) . . . . ?
C38 C41 C42 C43 178.0(2) . . . . ?
C41 C42 C43 C44 -0.8(4) . . . . ?
C42 C43 C44 C45 -0.6(4) . . . . ?
C43 C44 C45 C46 0.9(4) . . . . ?
C42 C41 C46 C45 -1.4(4) . . . . ?
C38 C41 C46 C45 -177.8(2) . . . . ?
C44 C45 C46 C41 0.1(4) . . . . ?
C32 C38 C51 C52 -149.1(2) . . . . ?
C41 C38 C51 C52 84.3(3) . . . . ?
C32 C38 C51 C56 32.2(3) . . . . ?
C41 C38 C51 C56 -94.5(3) . . . . ?
C56 C51 C52 C53 0.0(4) . . . . ?
C38 C51 C52 C53 -178.8(2) . . . . ?
C51 C52 C53 C54 1.1(4) . . . . ?
C52 C53 C54 C55 -1.2(5) . . . . ?
C53 C54 C55 C56 0.2(5) . . . . ?
C52 C51 C56 C55 -0.9(4) . . . . ?
C38 C51 C56 C55 177.8(2) . . . . ?
C54 C55 C56 C51 0.8(4) . . . . ?
C36 C39 C61 C62 -108.0(2) . . . . ?
C71 C39 C61 C62 125.2(2) . . . . ?
C36 C39 C61 C66 73.7(3) . . . . ?
C71 C39 C61 C66 -53.1(3) . . . . ?
C66 C61 C62 C63 0.0(3) . . . . ?
C39 C61 C62 C63 -178.4(2) . . . . ?
C61 C62 C63 C64 0.5(4) . . . . ?
C62 C63 C64 C65 -1.1(4) . . . . ?
C63 C64 C65 C66 1.2(4) . . . . ?
C64 C65 C66 C61 -0.7(4) . . . . ?
C62 C61 C66 C65 0.0(3) . . . . ?
C39 C61 C66 C65 178.4(2) . . . . ?
C36 C39 C71 C76 -25.0(3) . . . . ?
C61 C39 C71 C76 103.2(2) . . . . ?
C36 C39 C71 C72 156.2(2) . . . . ?
C61 C39 C71 C72 -75.6(3) . . . . ?
C76 C71 C72 C73 -0.5(4) . . . . ?
C39 C71 C72 C73 178.3(2) . . . . ?
C71 C72 C73 C74 1.3(4) . . . . ?
C72 C73 C74 C75 -1.1(4) . . . . ?
C73 C74 C75 C76 0.1(4) . . . . ?
C74 C75 C76 C71 0.7(4) . . . . ?
C72 C71 C76 C75 -0.5(3) . . . . ?
C39 C71 C76 C75 -179.2(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168327480
