#------------------------------------------------------------------------------
#$Date: 2023-07-06 00:54:47 +0300 (Thu, 06 Jul 2023) $
#$Revision: 284994 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/18/7131840.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_7131840
loop_
_publ_author_name
'Sahoo, Sipra Sucharita'
'Panda, Pradeepta'
_publ_section_title
;
 Bis(napthobipyrrolyl)methene derived Hexapyrrolic BODIPY as a Single
 Molecule Helicate with Near Infrared Emission
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC02336B
_journal_year                    2023
_chemical_formula_moiety         'C61 H67 B F2 N6 O4, 0.5(C H Cl3), 0.5(C6 H14)'
_chemical_formula_sum            'C64.5 H74.5 B Cl1.5 F2 N6 O4'
_chemical_formula_weight         1099.78
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2023-07-04
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-07-05 deposited with the CCDC.	2023-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.346(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1630(5)
_cell_length_b                   31.5920(8)
_cell_length_c                   13.5347(4)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.2
_cell_measurement_theta_min      2.9
_cell_volume                     5937.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            57010
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.953
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       block
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0032(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     834
_refine_ls_number_reflns         10428
_refine_ls_number_restraints     520
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0694
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1297P)²+1.0257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2036
_refine_ls_wR_factor_ref         0.2329
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6399
_reflns_number_total             10428
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc02336b2.cif
_cod_data_source_block           pkpbodipy
_cod_original_formula_sum        'C64.50 H74.50 B Cl1.50 F2 N6 O4'
_cod_database_code               7131840
_shelx_shelxl_version_number     2018/3
_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_max   0.971
_shelx_estimated_absorpt_t_min   0.958
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C62-Cl1 = C62-Cl2 = C62-Cl3
 1.74 with sigma of 0.02
 Cl1-Cl2 = Cl2-Cl3 = Cl3-Cl1
 2.84 with sigma of 0.02
 C63-C64 = C64-C65 = C65-C66 = C66-C67 = C67-C68
 1.53 with sigma of 0.02
 C48-C49 = C48-C50 = C46-C48
 1.53 with sigma of 0.02
 C48'-C49' = C48'-C50'
 1.53 with sigma of 0.02
 C46-C50 = C46-C49 = C46-C50' = C46-C49'
 2.5 with sigma of 0.02
 C49-C50 = C49'-C50'
 2.5 with sigma of 0.02
 C63-C65 = C64-C66 = C65-C67 = C66-C68
 2.49 with sigma of 0.02
 N1-H1 = N2-H2 = N5-H5 = N6-H6
 0.9 with sigma of 0.02
 O2-C2 = O2'-C2'
 1.46 with sigma of 0.02
 C1-C2 = C1'-C2'
 1.53 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C62 \\sim Cl1 \\sim Cl2 \\sim Cl3 \\sim C63 \\sim C64 \\sim C65 \\sim C66 \\sim
C67 \\sim C68: within 6A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 6A
C46 \\sim C48 \\sim C49 \\sim C50 \\sim C48' \\sim C49' \\sim C50': within 3A
with sigma of 0.02 and sigma for terminal atoms of 0.04 within 3A
N1 \\sim H1: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
within 2A
N2 \\sim H2: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
within 2A
N5 \\sim H5: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
within 2A
N6 \\sim H6: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
within 2A
C1 \\sim C2 \\sim C1' \\sim C2' \\sim O2 \\sim O2': within 2A with sigma of
0.02 and sigma for terminal atoms of 0.04 within 2A
4. Others
 Sof(C1')=Sof(H1'A)=Sof(H1'B)=Sof(H1'C)=Sof(C2')=Sof(H2'A)=Sof(H2'B)=Sof(O2')=
 1-FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(O2)=FVAR(1)
 Sof(C48')=Sof(H48')=Sof(C49')=Sof(H49D)=Sof(H49E)=Sof(H49F)=Sof(C50')=
 Sof(H50D)=Sof(H50E)=Sof(H50F)=1-FVAR(2)
 Sof(C48)=Sof(H48)=Sof(C49)=Sof(H49A)=Sof(H49B)=Sof(H49C)=Sof(C50)=Sof(H50A)=
 Sof(H50B)=Sof(H50C)=FVAR(2)
 Fixed Sof: C62(0.5) H62(0.5) Cl1(0.5) Cl2(0.5) Cl3(0.5) C63(0.5) H63A(0.5)
 H63B(0.5) H63C(0.5) C64(0.5) H64A(0.5) H64B(0.5) C65(0.5) H65A(0.5) H65B(0.5)
 C66(0.5) H66A(0.5) H66B(0.5) C67(0.5) H67A(0.5) H67B(0.5) C68(0.5) H68A(0.5)
 H68B(0.5) H68C(0.5)
5.a Ternary CH refined with riding coordinates:
 C13(H13), C28(H28), C34(H34), C48(H48), C48'(H48'), C62(H62)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C2'(H2'A,H2'B), C10(H10A,H10B), C52(H52A,H52B), C60(H60A,H60B),
 C64(H64A,H64B), C65(H65A,H65B), C66(H66A,H66B), C67(H67A,H67B)
5.c Me refined with riding coordinates:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C),
 C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C35(H35A,H35B,H35C), C36(H36A,H36B,
 H36C), C49(H49A,H49B,H49C), C50(H50A,H50B,H50C), C49'(H49D,H49E,H49F),
 C50'(H50D,H50E,H50F), C57(H57A,H57B,H57C), C58(H58A,H58B,H58C), C61(H61A,H61B,
 H61C)
5.d Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C20(H20), C21(H21), C31(H31), C39(H39), C40(H40),
 C41(H41), C42(H42)
5.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C1'(H1'A,H1'B,H1'C), C63(H63A,H63B,H63C), C68(H68A,H68B,H68C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.18682(18) 0.53300(9) 0.32936(19) 0.0966(8) Uani 1 1 d . . . . .
C1 C 0.1183(9) 0.5215(4) 0.0789(14) 0.141(5) Uani 0.544(17) 1 d D U P A 1
H1A H 0.167915 0.512224 0.044586 0.212 Uiso 0.544(17) 1 calc R U P A 1
H1B H 0.059164 0.525005 0.030936 0.212 Uiso 0.544(17) 1 calc R U P A 1
H1C H 0.109588 0.500691 0.128025 0.212 Uiso 0.544(17) 1 calc R U P A 1
C2 C 0.1461(11) 0.5615(4) 0.1288(11) 0.098(3) Uani 0.544(17) 1 d D U P A 1
H2A H 0.144232 0.583802 0.079086 0.117 Uiso 0.544(17) 1 calc R U P A 1
H2B H 0.101584 0.568874 0.172160 0.117 Uiso 0.544(17) 1 calc R U P A 1
O2 O 0.2427(13) 0.5576(5) 0.1881(19) 0.080(3) Uani 0.544(17) 1 d D U P A 1
C1' C 0.1306(12) 0.5476(8) 0.0343(8) 0.147(6) Uani 0.456(17) 1 d D U P A 2
H1'A H 0.162914 0.573313 0.023097 0.221 Uiso 0.456(17) 1 calc R U P A 2
H1'B H 0.064501 0.549025 0.000205 0.221 Uiso 0.456(17) 1 calc R U P A 2
H1'C H 0.161432 0.524062 0.008729 0.221 Uiso 0.456(17) 1 calc R U P A 2
C2' C 0.1351(12) 0.5420(7) 0.1417(10) 0.099(4) Uani 0.456(17) 1 d D U P A 2
H2'A H 0.109547 0.514395 0.154153 0.118 Uiso 0.456(17) 1 calc R U P A 2
H2'B H 0.096230 0.563403 0.166056 0.118 Uiso 0.456(17) 1 calc R U P A 2
O2' O 0.2345(17) 0.5454(7) 0.195(2) 0.088(4) Uani 0.456(17) 1 d D U P A 2
C3 C 0.2515(3) 0.54429(11) 0.2894(3) 0.0763(9) Uani 1 1 d . . . . .
C4 C 0.3498(2) 0.55067(9) 0.3419(2) 0.0644(8) Uani 1 1 d . . . . .
C5 C 0.4340(2) 0.56313(9) 0.3130(3) 0.0687(8) Uani 1 1 d . . . . .
C6 C 0.4499(3) 0.57213(11) 0.2089(3) 0.0897(11) Uani 1 1 d . . . . .
H6A H 0.515771 0.580148 0.212032 0.135 Uiso 1 1 calc R U . . .
H6B H 0.435649 0.547233 0.168047 0.135 Uiso 1 1 calc R U . . .
H6C H 0.408349 0.594796 0.179917 0.135 Uiso 1 1 calc R U . . .
C7 C 0.6081(3) 0.57745(13) 0.4083(3) 0.1043(13) Uani 1 1 d . . . . .
H7A H 0.618906 0.583900 0.342118 0.156 Uiso 1 1 calc R U . . .
H7B H 0.622725 0.601859 0.450809 0.156 Uiso 1 1 calc R U . . .
H7C H 0.648880 0.554358 0.436124 0.156 Uiso 1 1 calc R U . . .
C8 C 0.5050(2) 0.56533(9) 0.4019(3) 0.0692(8) Uani 1 1 d . . . . .
C9 C 0.4629(2) 0.55407(9) 0.4806(3) 0.0674(8) Uani 1 1 d . . . . .
C10 C 0.5041(2) 0.55016(9) 0.5913(2) 0.0785(10) Uani 1 1 d . . . . .
H10A H 0.572533 0.544537 0.599979 0.094 Uiso 1 1 calc R U . . .
H10B H 0.474680 0.525967 0.617457 0.094 Uiso 1 1 calc R U . . .
C11 C 0.4899(2) 0.58853(8) 0.6527(2) 0.0609(7) Uani 1 1 d . . . . .
C12 C 0.5362(2) 0.60102(9) 0.7480(2) 0.0642(8) Uani 1 1 d . . . . .
C13 C 0.6241(2) 0.58110(11) 0.8124(3) 0.0791(10) Uani 1 1 d . . . . .
H13 H 0.651861 0.602942 0.860894 0.095 Uiso 1 1 calc R U . . .
C14 C 0.7025(3) 0.56927(16) 0.7570(4) 0.1241(16) Uani 1 1 d . . . . .
H14A H 0.716486 0.592986 0.717888 0.186 Uiso 1 1 calc R U . . .
H14B H 0.759403 0.561470 0.804603 0.186 Uiso 1 1 calc R U . . .
H14C H 0.681637 0.545797 0.713018 0.186 Uiso 1 1 calc R U . . .
C15 C 0.6006(3) 0.54498(14) 0.8738(4) 0.1324(19) Uani 1 1 d . . . . .
H15A H 0.550471 0.553212 0.908463 0.199 Uiso 1 1 calc R U . . .
H15B H 0.579138 0.521375 0.830530 0.199 Uiso 1 1 calc R U . . .
H15C H 0.656903 0.537048 0.922115 0.199 Uiso 1 1 calc R U . . .
C16 C 0.4860(2) 0.63859(8) 0.7713(2) 0.0589(7) Uani 1 1 d . . . . .
C17 C 0.4962(2) 0.66544(10) 0.8595(2) 0.0665(8) Uani 1 1 d . . . . .
C18 C 0.5489(3) 0.65383(12) 0.9535(2) 0.0898(11) Uani 1 1 d . . . . .
H18 H 0.582092 0.628270 0.959993 0.108 Uiso 1 1 calc R U . . .
C19 C 0.5532(3) 0.67918(14) 1.0377(3) 0.1085(14) Uani 1 1 d . . . . .
H19 H 0.588066 0.670394 1.099843 0.130 Uiso 1 1 calc R U . . .
C20 C 0.5061(3) 0.71712(13) 1.0293(3) 0.0997(12) Uani 1 1 d . . . . .
H20 H 0.509794 0.734377 1.085623 0.120 Uiso 1 1 calc R U . . .
C21 C 0.4532(3) 0.72991(11) 0.9375(2) 0.0779(9) Uani 1 1 d . . . . .
H21 H 0.420279 0.755537 0.933296 0.093 Uiso 1 1 calc R U . . .
C22 C 0.4476(2) 0.70520(9) 0.8502(2) 0.0614(7) Uani 1 1 d . . . . .
C23 C 0.3883(2) 0.71686(8) 0.7538(2) 0.0562(7) Uani 1 1 d . . . . .
C24 C 0.3412(2) 0.75455(8) 0.7158(2) 0.0572(7) Uani 1 1 d . . . . .
C25 C 0.28931(19) 0.74482(8) 0.6186(2) 0.0555(7) Uani 1 1 d . . . . .
C26 C 0.36545(19) 0.68617(8) 0.6767(2) 0.0512(6) Uani 1 1 d . . . . .
C27 C 0.41549(19) 0.64719(8) 0.6869(2) 0.0556(7) Uani 1 1 d . . . . .
C28 C 0.3488(2) 0.79686(8) 0.7688(2) 0.0675(8) Uani 1 1 d . . . . .
H28 H 0.331841 0.791783 0.834560 0.081 Uiso 1 1 calc R U . . .
C29 C 0.4525(3) 0.81316(11) 0.7905(3) 0.0909(11) Uani 1 1 d . . . . .
H29A H 0.455056 0.840011 0.824109 0.136 Uiso 1 1 calc R U . . .
H29B H 0.493056 0.793286 0.832760 0.136 Uiso 1 1 calc R U . . .
H29C H 0.474580 0.816404 0.728237 0.136 Uiso 1 1 calc R U . . .
C30 C 0.2828(3) 0.83216(9) 0.7194(3) 0.0831(10) Uani 1 1 d . . . . .
H30A H 0.294376 0.857262 0.759976 0.125 Uiso 1 1 calc R U . . .
H30B H 0.295525 0.837854 0.653620 0.125 Uiso 1 1 calc R U . . .
H30C H 0.216905 0.823602 0.713610 0.125 Uiso 1 1 calc R U . . .
C31 C 0.2367(2) 0.76976(8) 0.5430(2) 0.0628(8) Uani 1 1 d . . . . .
H31 H 0.235981 0.798881 0.552893 0.075 Uiso 1 1 calc R U . . .
C32 C 0.1854(2) 0.75356(8) 0.4542(2) 0.0611(7) Uani 1 1 d . . . . .
C33 C 0.1305(2) 0.77415(9) 0.3690(2) 0.0668(8) Uani 1 1 d . . . . .
C34 C 0.1165(2) 0.82187(9) 0.3578(3) 0.0777(9) Uani 1 1 d . . . . .
H34 H 0.065900 0.826075 0.297906 0.093 Uiso 1 1 calc R U . . .
C35 C 0.2042(3) 0.84375(11) 0.3363(4) 0.1169(16) Uani 1 1 d . . . . .
H35A H 0.224988 0.829875 0.281181 0.175 Uiso 1 1 calc R U . . .
H35B H 0.188971 0.872750 0.318873 0.175 Uiso 1 1 calc R U . . .
H35C H 0.254732 0.842621 0.395004 0.175 Uiso 1 1 calc R U . . .
C36 C 0.0799(4) 0.84216(13) 0.4440(4) 0.1348(18) Uani 1 1 d . . . . .
H36A H 0.023936 0.827231 0.455200 0.202 Uiso 1 1 calc R U . . .
H36B H 0.129147 0.841022 0.503839 0.202 Uiso 1 1 calc R U . . .
H36C H 0.063386 0.871151 0.427708 0.202 Uiso 1 1 calc R U . . .
C37 C 0.0864(2) 0.74246(9) 0.3045(2) 0.0633(7) Uani 1 1 d . . . . .
C38 C 0.0248(2) 0.74233(10) 0.2048(2) 0.0694(8) Uani 1 1 d . . . . .
C39 C 0.0214(3) 0.77717(12) 0.1391(3) 0.0833(10) Uani 1 1 d . . . . .
H39 H 0.059791 0.800650 0.159839 0.100 Uiso 1 1 calc R U . . .
C40 C -0.0370(3) 0.77732(15) 0.0458(3) 0.1046(13) Uani 1 1 d . . . . .
H40 H -0.039524 0.800877 0.004186 0.126 Uiso 1 1 calc R U . . .
C41 C -0.0911(4) 0.74256(17) 0.0148(3) 0.1218(16) Uani 1 1 d . . . . .
H41 H -0.131732 0.742679 -0.048237 0.146 Uiso 1 1 calc R U . . .
C42 C -0.0871(3) 0.70696(14) 0.0751(3) 0.1060(13) Uani 1 1 d . . . . .
H42 H -0.124205 0.683477 0.051098 0.127 Uiso 1 1 calc R U . . .
C43 C -0.0287(2) 0.70544(11) 0.1710(2) 0.0745(9) Uani 1 1 d . . . . .
C44 C -0.0165(2) 0.66758(10) 0.2350(2) 0.0677(8) Uani 1 1 d . . . . .
C45 C 0.0567(2) 0.66681(9) 0.3202(2) 0.0592(7) Uani 1 1 d . . . . .
C46 C -0.0660(2) 0.62822(10) 0.2322(2) 0.0724(8) Uani 1 1 d D U . . .
C47 C 0.1101(2) 0.70318(8) 0.3560(2) 0.0575(7) Uani 1 1 d . . . . .
C48 C -0.1581(6) 0.6150(3) 0.1561(11) 0.096(2) Uani 0.787(13) 1 d D U P B 3
H48 H -0.183165 0.641585 0.124162 0.115 Uiso 0.787(13) 1 calc R U P B 3
C49 C -0.2360(4) 0.5994(4) 0.2041(5) 0.152(3) Uani 0.787(13) 1 d D U P B 3
H49A H -0.245103 0.618622 0.256317 0.228 Uiso 0.787(13) 1 calc R U P B 3
H49B H -0.294547 0.597336 0.154630 0.228 Uiso 0.787(13) 1 calc R U P B 3
H49C H -0.219241 0.571926 0.232810 0.228 Uiso 0.787(13) 1 calc R U P B 3
C50 C -0.1311(5) 0.5897(3) 0.0717(6) 0.136(3) Uani 0.787(13) 1 d D U P B 3
H50A H -0.079568 0.603660 0.047992 0.204 Uiso 0.787(13) 1 calc R U P B 3
H50B H -0.110542 0.561930 0.095635 0.204 Uiso 0.787(13) 1 calc R U P B 3
H50C H -0.185848 0.587341 0.017456 0.204 Uiso 0.787(13) 1 calc R U P B 3
C48' C -0.1389(19) 0.6120(11) 0.163(5) 0.102(6) Uani 0.213(13) 1 d D U P B 4
H48' H -0.128110 0.627265 0.103076 0.122 Uiso 0.213(13) 1 calc R U P B 4
C49' C -0.2394(12) 0.6279(11) 0.167(3) 0.134(8) Uani 0.213(13) 1 d D U P B 4
H49D H -0.285398 0.614496 0.114713 0.201 Uiso 0.213(13) 1 calc R U P B 4
H49E H -0.254233 0.621351 0.231298 0.201 Uiso 0.213(13) 1 calc R U P B 4
H49F H -0.242025 0.658045 0.156851 0.201 Uiso 0.213(13) 1 calc R U P B 4
C50' C -0.1391(18) 0.5671(7) 0.124(2) 0.129(8) Uani 0.213(13) 1 d D U P B 4
H50D H -0.197303 0.562070 0.075950 0.193 Uiso 0.213(13) 1 calc R U P B 4
H50E H -0.084573 0.562893 0.093214 0.193 Uiso 0.213(13) 1 calc R U P B 4
H50F H -0.135669 0.547708 0.179707 0.193 Uiso 0.213(13) 1 calc R U P B 4
C51 C -0.0199(2) 0.60499(9) 0.3148(2) 0.0664(8) Uani 1 1 d . . . . .
C52 C -0.0359(2) 0.56143(10) 0.3540(3) 0.0779(9) Uani 1 1 d . . . . .
H52A H -0.104454 0.555568 0.341075 0.093 Uiso 1 1 calc R U . . .
H52B H -0.005711 0.540702 0.317378 0.093 Uiso 1 1 calc R U . . .
C53 C 0.0034(2) 0.55655(9) 0.4640(3) 0.0655(8) Uani 1 1 d . . . . .
C54 C -0.0375(2) 0.56334(10) 0.5457(3) 0.0762(9) Uani 1 1 d . . . . .
C55 C 0.0330(2) 0.55599(10) 0.6338(3) 0.0738(9) Uani 1 1 d . . . . .
C56 C 0.1158(2) 0.54469(9) 0.6008(2) 0.0656(8) Uani 1 1 d . . . . .
C57 C -0.1395(3) 0.57701(17) 0.5425(4) 0.1239(16) Uani 1 1 d . . . . .
H57A H -0.150540 0.579560 0.610009 0.186 Uiso 1 1 calc R U . . .
H57B H -0.150427 0.603876 0.509066 0.186 Uiso 1 1 calc R U . . .
H57C H -0.182736 0.556361 0.506467 0.186 Uiso 1 1 calc R U . . .
C58 C 0.0168(3) 0.56001(15) 0.7394(3) 0.1143(14) Uani 1 1 d . . . . .
H58A H -0.048616 0.568436 0.737948 0.171 Uiso 1 1 calc R U . . .
H58B H 0.028745 0.533247 0.773097 0.171 Uiso 1 1 calc R U . . .
H58C H 0.059727 0.580921 0.774761 0.171 Uiso 1 1 calc R U . . .
C59 C 0.2119(3) 0.53445(11) 0.6508(3) 0.0776(9) Uani 1 1 d . . . . .
C60 C 0.3246(3) 0.53239(19) 0.8051(3) 0.1278(17) Uani 1 1 d . . . . .
H60A H 0.346742 0.504058 0.793809 0.153 Uiso 1 1 calc R U . . .
H60B H 0.366037 0.552398 0.779680 0.153 Uiso 1 1 calc R U . . .
C61 C 0.3312(5) 0.5388(3) 0.9078(4) 0.193(3) Uani 1 1 d . . . . .
H61A H 0.396848 0.535206 0.941997 0.290 Uiso 1 1 calc R U . . .
H61B H 0.310364 0.567026 0.919079 0.290 Uiso 1 1 calc R U . . .
H61C H 0.291096 0.518749 0.933190 0.290 Uiso 1 1 calc R U . . .
B1 B 0.2346(2) 0.67715(9) 0.5134(2) 0.0562(8) Uani 1 1 d . . . . .
N1 N 0.36939(19) 0.54513(8) 0.4440(2) 0.0652(7) Uani 1 1 d D U . . .
N2 N 0.41766(17) 0.61617(7) 0.61748(18) 0.0598(6) Uani 1 1 d D U . . .
N3 N 0.30143(16) 0.70183(6) 0.59736(16) 0.0530(6) Uani 1 1 d . . . . .
N4 N 0.17444(16) 0.70968(6) 0.44321(17) 0.0562(6) Uani 1 1 d . . . . .
N5 N 0.05463(17) 0.62856(7) 0.36621(19) 0.0613(6) Uani 1 1 d D U . . .
N6 N 0.09543(19) 0.54504(8) 0.4985(2) 0.0658(7) Uani 1 1 d D U . . .
O3 O 0.27591(18) 0.52442(9) 0.6072(2) 0.0979(8) Uani 1 1 d . . . . .
O4 O 0.22718(18) 0.53757(9) 0.75116(19) 0.0980(8) Uani 1 1 d . . . . .
F1 F 0.28698(13) 0.65208(5) 0.45909(12) 0.0751(5) Uani 1 1 d . . . . .
F2 F 0.17475(13) 0.65018(5) 0.55488(12) 0.0774(5) Uani 1 1 d . . . . .
H2 H 0.3808(17) 0.6166(9) 0.5581(14) 0.058(7) Uiso 1 1 d D U . . .
H5 H 0.0879(19) 0.6229(10) 0.4299(15) 0.073(7) Uiso 1 1 d D U . . .
H1 H 0.3307(19) 0.5364(9) 0.483(2) 0.065(7) Uiso 1 1 d D U . . .
H6 H 0.133(2) 0.5400(10) 0.458(2) 0.072(8) Uiso 1 1 d D U . . .
C62 C 0.7582(12) 0.7133(4) 0.6923(11) 0.207(5) Uani 0.5 1 d D U P C 1
H62 H 0.801344 0.729698 0.658491 0.249 Uiso 0.5 1 calc R U P C 1
Cl1 Cl 0.8231(3) 0.67387(11) 0.7810(3) 0.1889(15) Uani 0.5 1 d D U P C 1
Cl2 Cl 0.6769(4) 0.68168(16) 0.6078(4) 0.207(2) Uani 0.5 1 d D U P C 1
Cl3 Cl 0.6961(5) 0.74456(18) 0.7613(4) 0.217(3) Uani 0.5 1 d D U P C 1
C63 C 0.7330(15) 0.7913(5) 0.8246(15) 0.281(7) Uani 0.5 1 d D U P D 2
H63A H 0.708142 0.776970 0.876673 0.422 Uiso 0.5 1 calc R U P D 2
H63B H 0.696134 0.816470 0.805183 0.422 Uiso 0.5 1 calc R U P D 2
H63C H 0.799152 0.798720 0.849369 0.422 Uiso 0.5 1 calc R U P D 2
C64 C 0.7260(19) 0.7621(5) 0.7335(16) 0.227(6) Uani 0.5 1 d D U P D 2
H64A H 0.788721 0.759608 0.715463 0.273 Uiso 0.5 1 calc R U P D 2
H64B H 0.681777 0.774108 0.676551 0.273 Uiso 0.5 1 calc R U P D 2
C65 C 0.6884(16) 0.7157(5) 0.7591(15) 0.227(5) Uani 0.5 1 d D U P D 2
H65A H 0.700948 0.709521 0.830654 0.272 Uiso 0.5 1 calc R U P D 2
H65B H 0.621119 0.710889 0.729694 0.272 Uiso 0.5 1 calc R U P D 2
C66 C 0.7608(15) 0.6915(6) 0.6999(15) 0.253(5) Uani 0.5 1 d D U P D 2
H66A H 0.825737 0.702676 0.717379 0.304 Uiso 0.5 1 calc R U P D 2
H66B H 0.761862 0.661253 0.712246 0.304 Uiso 0.5 1 calc R U P D 2
C67 C 0.7126(14) 0.7023(7) 0.5898(14) 0.237(5) Uani 0.5 1 d D U P D 2
H67A H 0.704948 0.732713 0.582334 0.285 Uiso 0.5 1 calc R U P D 2
H67B H 0.753331 0.692719 0.544361 0.285 Uiso 0.5 1 calc R U P D 2
C68 C 0.6200(14) 0.6821(7) 0.5642(17) 0.255(7) Uani 0.5 1 d D U P D 2
H68A H 0.627833 0.651974 0.571523 0.382 Uiso 0.5 1 calc R U P D 2
H68B H 0.590889 0.688661 0.495756 0.382 Uiso 0.5 1 calc R U P D 2
H68C H 0.579412 0.692069 0.608345 0.382 Uiso 0.5 1 calc R U P D 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'
B B 0.0013 0.0007 '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'
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'
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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
O2 C2 C1 108.8(12) . . ?
O2 C2 H2A 109.9 . . ?
O2 C2 H2B 109.9 . . ?
C3 O2 C2 117.1(16) . . ?
H1'A C1' H1'B 109.5 . . ?
H1'A C1' H1'C 109.5 . . ?
H1'B C1' H1'C 109.5 . . ?
C2' C1' H1'A 109.5 . . ?
C2' C1' H1'B 109.5 . . ?
C2' C1' H1'C 109.5 . . ?
C1' C2' H2'A 109.8 . . ?
C1' C2' H2'B 109.8 . . ?
C1' C2' O2' 109.5(16) . . ?
H2'A C2' H2'B 108.2 . . ?
O2' C2' H2'A 109.8 . . ?
O2' C2' H2'B 109.8 . . ?
C3 O2' C2' 118(2) . . ?
O1 C3 O2 126.3(8) . . ?
O1 C3 O2' 117.0(11) . . ?
O1 C3 C4 124.3(3) . . ?
O2 C3 C4 109.1(8) . . ?
O2' C3 C4 118.1(11) . . ?
C5 C4 C3 134.4(3) . . ?
N1 C4 C3 117.6(3) . . ?
N1 C4 C5 107.9(3) . . ?
C4 C5 C6 128.1(3) . . ?
C4 C5 C8 106.4(3) . . ?
C8 C5 C6 125.5(3) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
C5 C8 C7 125.9(3) . . ?
C9 C8 C5 107.8(3) . . ?
C9 C8 C7 126.3(3) . . ?
C8 C9 C10 131.0(3) . . ?
N1 C9 C8 108.4(3) . . ?
N1 C9 C10 120.6(3) . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
C9 C10 C11 114.6(2) . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C12 C11 C10 130.8(3) . . ?
N2 C11 C10 119.8(2) . . ?
N2 C11 C12 109.3(2) . . ?
C11 C12 C13 127.2(3) . . ?
C11 C12 C16 105.9(2) . . ?
C16 C12 C13 126.8(3) . . ?
C12 C13 H13 105.7 . . ?
C14 C13 C12 114.9(3) . . ?
C14 C13 H13 105.7 . . ?
C15 C13 C12 113.1(3) . . ?
C15 C13 H13 105.7 . . ?
C15 C13 C14 110.9(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C12 133.2(3) . . ?
C27 C16 C12 106.6(2) . . ?
C27 C16 C17 120.2(2) . . ?
C18 C17 C16 123.2(3) . . ?
C18 C17 C22 118.4(3) . . ?
C22 C17 C16 118.3(3) . . ?
C17 C18 H18 119.0 . . ?
C19 C18 C17 122.0(3) . . ?
C19 C18 H18 119.0 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.9(3) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.1(3) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.2 . . ?
C20 C21 C22 121.7(3) . . ?
C22 C21 H21 119.2 . . ?
C17 C22 C23 119.1(2) . . ?
C21 C22 C17 117.9(3) . . ?
C21 C22 C23 122.7(3) . . ?
C24 C23 C22 133.6(2) . . ?
C24 C23 C26 106.6(2) . . ?
C26 C23 C22 119.7(2) . . ?
C23 C24 C28 126.1(3) . . ?
C25 C24 C23 106.2(2) . . ?
C25 C24 C28 127.7(2) . . ?
C31 C25 C24 132.1(2) . . ?
C31 C25 N3 117.9(2) . . ?
N3 C25 C24 109.9(2) . . ?
C27 C26 C23 119.2(2) . . ?
N3 C26 C23 110.8(2) . . ?
N3 C26 C27 129.7(2) . . ?
C16 C27 C26 121.1(2) . . ?
N2 C27 C16 108.5(2) . . ?
N2 C27 C26 129.7(2) . . ?
C24 C28 H28 106.2 . . ?
C24 C28 C29 111.4(3) . . ?
C24 C28 C30 117.3(3) . . ?
C29 C28 H28 106.2 . . ?
C30 C28 H28 106.2 . . ?
C30 C28 C29 108.8(3) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C25 C31 H31 118.4 . . ?
C32 C31 C25 123.3(2) . . ?
C32 C31 H31 118.4 . . ?
C31 C32 C33 130.7(3) . . ?
C31 C32 N4 119.3(2) . . ?
N4 C32 C33 109.7(2) . . ?
C32 C33 C34 125.1(3) . . ?
C37 C33 C32 106.7(2) . . ?
C37 C33 C34 128.0(3) . . ?
C33 C34 H34 106.0 . . ?
C35 C34 C33 112.3(3) . . ?
C35 C34 H34 106.0 . . ?
C35 C34 C36 112.2(4) . . ?
C36 C34 C33 113.7(3) . . ?
C36 C34 H34 106.0 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C33 C37 C38 134.1(3) . . ?
C33 C37 C47 106.6(3) . . ?
C47 C37 C38 119.3(3) . . ?
C39 C38 C37 121.5(3) . . ?
C39 C38 C43 119.3(3) . . ?
C43 C38 C37 119.1(3) . . ?
C38 C39 H39 119.2 . . ?
C40 C39 C38 121.7(4) . . ?
C40 C39 H39 119.2 . . ?
C39 C40 H40 120.5 . . ?
C41 C40 C39 119.0(4) . . ?
C41 C40 H40 120.5 . . ?
C40 C41 H41 119.4 . . ?
C40 C41 C42 121.3(4) . . ?
C42 C41 H41 119.4 . . ?
C41 C42 H42 119.2 . . ?
C41 C42 C43 121.6(4) . . ?
C43 C42 H42 119.2 . . ?
C38 C43 C44 119.2(3) . . ?
C42 C43 C38 116.9(3) . . ?
C42 C43 C44 123.8(3) . . ?
C45 C44 C43 119.0(3) . . ?
C45 C44 C46 106.8(3) . . ?
C46 C44 C43 134.2(3) . . ?
C44 C45 C47 122.2(3) . . ?
N5 C45 C44 108.4(3) . . ?
N5 C45 C47 128.7(3) . . ?
C44 C46 C48 126.8(5) . . ?
C48' C46 C44 131(3) . . ?
C48' C46 C51 122(2) . . ?
C51 C46 C44 106.8(3) . . ?
C51 C46 C48 126.3(6) . . ?
C45 C47 C37 118.8(3) . . ?
N4 C47 C37 110.2(2) . . ?
N4 C47 C45 130.2(2) . . ?
C46 C48 H48 104.2 . . ?
C49 C48 C46 113.7(10) . . ?
C49 C48 H48 104.2 . . ?
C49 C48 C50 118.9(7) . . ?
C50 C48 C46 109.9(6) . . ?
C50 C48 H48 104.2 . . ?
C48 C49 H49A 109.5 . . ?
C48 C49 H49B 109.5 . . ?
C48 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C48 C50 H50A 109.5 . . ?
C48 C50 H50B 109.5 . . ?
C48 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C46 C48' H48' 99.5 . . ?
C46 C48' C49' 116(2) . . ?
C46 C48' C50' 123(3) . . ?
C49' C48' H48' 99.5 . . ?
C50' C48' H48' 99.5 . . ?
C50' C48' C49' 112.6(19) . . ?
C48' C49' H49D 109.5 . . ?
C48' C49' H49E 109.5 . . ?
C48' C49' H49F 109.5 . . ?
H49D C49' H49E 109.5 . . ?
H49D C49' H49F 109.5 . . ?
H49E C49' H49F 109.5 . . ?
C48' C50' H50D 109.5 . . ?
C48' C50' H50E 109.5 . . ?
C48' C50' H50F 109.5 . . ?
H50D C50' H50E 109.5 . . ?
H50D C50' H50F 109.5 . . ?
H50E C50' H50F 109.5 . . ?
C46 C51 C52 133.3(3) . . ?
N5 C51 C46 108.4(3) . . ?
N5 C51 C52 118.2(3) . . ?
C51 C52 H52A 109.0 . . ?
C51 C52 H52B 109.0 . . ?
H52A C52 H52B 107.8 . . ?
C53 C52 C51 113.1(3) . . ?
C53 C52 H52A 109.0 . . ?
C53 C52 H52B 109.0 . . ?
C54 C53 C52 131.2(3) . . ?
N6 C53 C52 121.4(3) . . ?
N6 C53 C54 107.4(3) . . ?
C53 C54 C55 108.3(3) . . ?
C53 C54 C57 125.7(4) . . ?
C55 C54 C57 126.0(3) . . ?
C54 C55 C58 125.0(3) . . ?
C56 C55 C54 105.9(3) . . ?
C56 C55 C58 129.1(3) . . ?
C55 C56 C59 133.9(3) . . ?
N6 C56 C55 107.7(3) . . ?
N6 C56 C59 118.4(3) . . ?
C54 C57 H57A 109.5 . . ?
C54 C57 H57B 109.5 . . ?
C54 C57 H57C 109.5 . . ?
H57A C57 H57B 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C55 C58 H58A 109.5 . . ?
C55 C58 H58B 109.5 . . ?
C55 C58 H58C 109.5 . . ?
H58A C58 H58B 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
O3 C59 C56 123.9(3) . . ?
O3 C59 O4 121.6(3) . . ?
O4 C59 C56 114.4(3) . . ?
H60A C60 H60B 108.0 . . ?
C61 C60 H60A 109.4 . . ?
C61 C60 H60B 109.4 . . ?
C61 C60 O4 111.1(5) . . ?
O4 C60 H60A 109.4 . . ?
O4 C60 H60B 109.4 . . ?
C60 C61 H61A 109.5 . . ?
C60 C61 H61B 109.5 . . ?
C60 C61 H61C 109.5 . . ?
H61A C61 H61B 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
N4 B1 N3 107.6(2) . . ?
F1 B1 N3 111.4(2) . . ?
F1 B1 N4 110.0(2) . . ?
F1 B1 F2 107.1(2) . . ?
F2 B1 N3 110.3(2) . . ?
F2 B1 N4 110.5(2) . . ?
C4 N1 H1 129(2) . . ?
C9 N1 C4 109.5(3) . . ?
C9 N1 H1 122(2) . . ?
C11 N2 C27 109.8(2) . . ?
C11 N2 H2 127.6(18) . . ?
C27 N2 H2 122.4(18) . . ?
C25 N3 B1 123.9(2) . . ?
C26 N3 C25 106.3(2) . . ?
C26 N3 B1 128.2(2) . . ?
C32 N4 B1 124.0(2) . . ?
C47 N4 C32 106.5(2) . . ?
C47 N4 B1 129.2(2) . . ?
C45 N5 C51 109.6(2) . . ?
C45 N5 H5 123(2) . . ?
C51 N5 H5 125.1(19) . . ?
C53 N6 C56 110.7(3) . . ?
C53 N6 H6 121(2) . . ?
C56 N6 H6 128(2) . . ?
C59 O4 C60 117.1(3) . . ?
Cl1 C62 H62 112.6 . . ?
Cl2 C62 H62 112.6 . . ?
Cl2 C62 Cl1 102.5(7) . . ?
Cl3 C62 H62 112.6 . . ?
Cl3 C62 Cl1 106.1(8) . . ?
Cl3 C62 Cl2 109.8(10) . . ?
H63A C63 H63B 109.5 . . ?
H63A C63 H63C 109.5 . . ?
H63B C63 H63C 109.5 . . ?
C64 C63 H63A 109.5 . . ?
C64 C63 H63B 109.5 . . ?
C64 C63 H63C 109.5 . . ?
C63 C64 H64A 109.6 . . ?
C63 C64 H64B 109.6 . . ?
C63 C64 C65 110.2(14) . . ?
H64A C64 H64B 108.1 . . ?
C65 C64 H64A 109.6 . . ?
C65 C64 H64B 109.6 . . ?
C64 C65 H65A 113.1 . . ?
C64 C65 H65B 113.1 . . ?
H65A C65 H65B 110.5 . . ?
C66 C65 C64 93.2(12) . . ?
C66 C65 H65A 113.1 . . ?
C66 C65 H65B 113.1 . . ?
C65 C66 H66A 111.8 . . ?
C65 C66 H66B 111.8 . . ?
H66A C66 H66B 109.5 . . ?
C67 C66 C65 99.8(12) . . ?
C67 C66 H66A 111.8 . . ?
C67 C66 H66B 111.8 . . ?
C66 C67 H67A 109.7 . . ?
C66 C67 H67B 109.7 . . ?
H67A C67 H67B 108.2 . . ?
C68 C67 C66 110.0(14) . . ?
C68 C67 H67A 109.7 . . ?
C68 C67 H67B 109.7 . . ?
C67 C68 H68A 109.5 . . ?
C67 C68 H68B 109.5 . . ?
C67 C68 H68C 109.5 . . ?
H68A C68 H68B 109.5 . . ?
H68A C68 H68C 109.5 . . ?
H68B C68 H68C 109.5 . . ?
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 C3 1.206(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.453(14) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 O2 1.449(13) . ?
O2 C3 1.42(2) . ?
C1' H1'A 0.9600 . ?
C1' H1'B 0.9600 . ?
C1' H1'C 0.9600 . ?
C1' C2' 1.454(15) . ?
C2' H2'A 0.9700 . ?
C2' H2'B 0.9700 . ?
C2' O2' 1.454(15) . ?
O2' C3 1.25(3) . ?
C3 C4 1.447(5) . ?
C4 C5 1.384(4) . ?
C4 N1 1.366(4) . ?
C5 C6 1.497(5) . ?
C5 C8 1.410(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C7 C8 1.495(5) . ?
C8 C9 1.366(5) . ?
C9 C10 1.501(4) . ?
C9 N1 1.350(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.506(4) . ?
C11 C12 1.384(4) . ?
C11 N2 1.358(3) . ?
C12 C13 1.509(4) . ?
C12 C16 1.450(4) . ?
C13 H13 0.9800 . ?
C13 C14 1.505(5) . ?
C13 C15 1.488(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.448(4) . ?
C16 C27 1.388(4) . ?
C17 C18 1.391(4) . ?
C17 C22 1.426(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.384(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.365(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.380(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.406(4) . ?
C22 C23 1.453(4) . ?
C23 C24 1.412(4) . ?
C23 C26 1.414(4) . ?
C24 C25 1.409(4) . ?
C24 C28 1.511(4) . ?
C25 C31 1.387(4) . ?
C25 N3 1.406(3) . ?
C26 C27 1.414(4) . ?
C26 N3 1.356(3) . ?
C27 N2 1.362(3) . ?
C28 H28 0.9800 . ?
C28 C29 1.529(5) . ?
C28 C30 1.522(4) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31 0.9300 . ?
C31 C32 1.375(4) . ?
C32 C33 1.416(4) . ?
C32 N4 1.400(3) . ?
C33 C34 1.524(4) . ?
C33 C37 1.392(4) . ?
C34 H34 0.9800 . ?
C34 C35 1.499(5) . ?
C34 C36 1.509(5) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 C38 1.457(4) . ?
C37 C47 1.430(4) . ?
C38 C39 1.409(4) . ?
C38 C43 1.415(4) . ?
C39 H39 0.9300 . ?
C39 C40 1.366(5) . ?
C40 H40 0.9300 . ?
C40 C41 1.358(6) . ?
C41 H41 0.9300 . ?
C41 C42 1.384(6) . ?
C42 H42 0.9300 . ?
C42 C43 1.397(5) . ?
C43 C44 1.466(4) . ?
C44 C45 1.392(4) . ?
C44 C46 1.424(4) . ?
C45 C47 1.408(4) . ?
C45 N5 1.362(3) . ?
C46 C48 1.552(10) . ?
C46 C48' 1.35(4) . ?
C46 C51 1.389(4) . ?
C47 N4 1.358(3) . ?
C48 H48 0.9800 . ?
C48 C49 1.471(11) . ?
C48 C50 1.504(11) . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
C48' H48' 0.9800 . ?
C48' C49' 1.520(19) . ?
C48' C50' 1.51(2) . ?
C49' H49D 0.9600 . ?
C49' H49E 0.9600 . ?
C49' H49F 0.9600 . ?
C50' H50D 0.9600 . ?
C50' H50E 0.9600 . ?
C50' H50F 0.9600 . ?
C51 C52 1.508(4) . ?
C51 N5 1.365(4) . ?
C52 H52A 0.9700 . ?
C52 H52B 0.9700 . ?
C52 C53 1.491(4) . ?
C53 C54 1.363(5) . ?
C53 N6 1.345(4) . ?
C54 C55 1.416(5) . ?
C54 C57 1.500(5) . ?
C55 C56 1.381(4) . ?
C55 C58 1.497(5) . ?
C56 C59 1.433(5) . ?
C56 N6 1.358(4) . ?
C57 H57A 0.9600 . ?
C57 H57B 0.9600 . ?
C57 H57C 0.9600 . ?
C58 H58A 0.9600 . ?
C58 H58B 0.9600 . ?
C58 H58C 0.9600 . ?
C59 O3 1.218(4) . ?
C59 O4 1.336(4) . ?
C60 H60A 0.9700 . ?
C60 H60B 0.9700 . ?
C60 C61 1.390(7) . ?
C60 O4 1.438(5) . ?
C61 H61A 0.9600 . ?
C61 H61B 0.9600 . ?
C61 H61C 0.9600 . ?
B1 N3 1.540(4) . ?
B1 N4 1.538(4) . ?
B1 F1 1.390(4) . ?
B1 F2 1.395(4) . ?
N1 H1 0.878(17) . ?
N2 H2 0.869(17) . ?
N5 H5 0.915(17) . ?
N6 H6 0.851(17) . ?
C62 H62 0.9800 . ?
C62 Cl1 1.845(13) . ?
C62 Cl2 1.765(14) . ?
C62 Cl3 1.716(15) . ?
C63 H63A 0.9600 . ?
C63 H63B 0.9600 . ?
C63 H63C 0.9600 . ?
C63 C64 1.527(16) . ?
C64 H64A 0.9700 . ?
C64 H64B 0.9700 . ?
C64 C65 1.620(17) . ?
C65 H65A 0.9700 . ?
C65 H65B 0.9700 . ?
C65 C66 1.612(17) . ?
C66 H66A 0.9700 . ?
C66 H66B 0.9700 . ?
C66 C67 1.550(16) . ?
C67 H67A 0.9700 . ?
C67 H67B 0.9700 . ?
C67 C68 1.439(16) . ?
C68 H68A 0.9600 . ?
C68 H68B 0.9600 . ?
C68 H68C 0.9600 . ?
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
_geom_hbond_publ_flag
N2 H2 F1 0.869(17) 2.03(2) 2.783(3) 145(2) . yes
N5 H5 N6 0.915(17) 2.62(3) 3.177(3) 120(2) . yes
N5 H5 F2 0.915(17) 2.07(2) 2.859(3) 143(3) . yes
N1 H1 O3 0.878(17) 2.02(2) 2.866(4) 161(3) . yes
N6 H6 O1 0.851(17) 2.05(2) 2.868(4) 162(3) . yes
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
O1 C3 C4 C5 179.9(3) . . . . ?
O1 C3 C4 N1 -2.7(5) . . . . ?
C1 C2 O2 C3 -91(2) . . . . ?
C2 O2 C3 O1 5.8(18) . . . . ?
C2 O2 C3 C4 -168.1(10) . . . . ?
O2 C3 C4 C5 -6.1(10) . . . . ?
O2 C3 C4 N1 171.3(9) . . . . ?
C1' C2' O2' C3 175(2) . . . . ?
C2' O2' C3 O1 13(2) . . . . ?
C2' O2' C3 C4 -175.8(11) . . . . ?
O2' C3 C4 C5 9.2(13) . . . . ?
O2' C3 C4 N1 -173.4(12) . . . . ?
C3 C4 C5 C6 -3.9(5) . . . . ?
C3 C4 C5 C8 176.9(3) . . . . ?
C3 C4 N1 C9 -177.4(2) . . . . ?
C4 C5 C8 C7 179.9(3) . . . . ?
C4 C5 C8 C9 0.4(3) . . . . ?
C5 C4 N1 C9 0.6(3) . . . . ?
C5 C8 C9 C10 178.9(3) . . . . ?
C5 C8 C9 N1 -0.1(3) . . . . ?
C6 C5 C8 C7 0.7(5) . . . . ?
C6 C5 C8 C9 -178.8(3) . . . . ?
C7 C8 C9 C10 -0.6(5) . . . . ?
C7 C8 C9 N1 -179.5(3) . . . . ?
C8 C9 C10 C11 96.2(4) . . . . ?
C8 C9 N1 C4 -0.3(3) . . . . ?
C9 C10 C11 C12 -161.7(3) . . . . ?
C9 C10 C11 N2 22.6(4) . . . . ?
C10 C9 N1 C4 -179.4(2) . . . . ?
C10 C11 C12 C13 8.0(6) . . . . ?
C10 C11 C12 C16 -174.9(3) . . . . ?
C10 C11 N2 C27 177.2(3) . . . . ?
C11 C12 C13 C14 42.9(5) . . . . ?
C11 C12 C13 C15 -85.8(5) . . . . ?
C11 C12 C16 C17 177.0(3) . . . . ?
C11 C12 C16 C27 -2.5(3) . . . . ?
C12 C11 N2 C27 0.7(3) . . . . ?
C12 C16 C17 C18 -14.6(6) . . . . ?
C12 C16 C17 C22 167.3(3) . . . . ?
C12 C16 C27 C26 -167.8(3) . . . . ?
C12 C16 C27 N2 2.9(3) . . . . ?
C13 C12 C16 C17 -5.8(6) . . . . ?
C13 C12 C16 C27 174.7(3) . . . . ?
C16 C12 C13 C14 -133.7(4) . . . . ?
C16 C12 C13 C15 97.6(4) . . . . ?
C16 C17 C18 C19 -176.5(4) . . . . ?
C16 C17 C22 C21 176.2(3) . . . . ?
C16 C17 C22 C23 1.3(4) . . . . ?
C16 C27 N2 C11 -2.3(3) . . . . ?
C17 C16 C27 C26 12.6(4) . . . . ?
C17 C16 C27 N2 -176.7(3) . . . . ?
C17 C18 C19 C20 -1.1(7) . . . . ?
C17 C22 C23 C24 -171.0(3) . . . . ?
C17 C22 C23 C26 11.3(4) . . . . ?
C18 C17 C22 C21 -2.0(5) . . . . ?
C18 C17 C22 C23 -176.8(3) . . . . ?
C18 C19 C20 C21 1.0(7) . . . . ?
C19 C20 C21 C22 -1.5(6) . . . . ?
C20 C21 C22 C17 2.0(5) . . . . ?
C20 C21 C22 C23 176.6(3) . . . . ?
C21 C22 C23 C24 14.4(5) . . . . ?
C21 C22 C23 C26 -163.3(3) . . . . ?
C22 C17 C18 C19 1.6(6) . . . . ?
C22 C23 C24 C25 -176.0(3) . . . . ?
C22 C23 C24 C28 5.9(5) . . . . ?
C22 C23 C26 C27 -12.3(4) . . . . ?
C22 C23 C26 N3 173.4(2) . . . . ?
C23 C24 C25 C31 -173.9(3) . . . . ?
C23 C24 C25 N3 1.6(3) . . . . ?
C23 C24 C28 C29 60.7(4) . . . . ?
C23 C24 C28 C30 -173.0(3) . . . . ?
C23 C26 C27 C16 0.4(4) . . . . ?
C23 C26 C27 N2 -168.2(3) . . . . ?
C23 C26 N3 C25 5.7(3) . . . . ?
C23 C26 N3 B1 -159.9(3) . . . . ?
C24 C23 C26 C27 169.5(2) . . . . ?
C24 C23 C26 N3 -4.8(3) . . . . ?
C24 C25 C31 C32 -175.7(3) . . . . ?
C24 C25 N3 C26 -4.5(3) . . . . ?
C24 C25 N3 B1 161.9(2) . . . . ?
C25 C24 C28 C29 -117.0(3) . . . . ?
C25 C24 C28 C30 9.3(5) . . . . ?
C25 C31 C32 C33 -178.1(3) . . . . ?
C25 C31 C32 N4 8.7(4) . . . . ?
C26 C23 C24 C25 1.9(3) . . . . ?
C26 C23 C24 C28 -176.3(3) . . . . ?
C26 C27 N2 C11 167.4(3) . . . . ?
C27 C16 C17 C18 164.8(3) . . . . ?
C27 C16 C17 C22 -13.3(4) . . . . ?
C27 C26 N3 C25 -167.8(3) . . . . ?
C27 C26 N3 B1 26.6(4) . . . . ?
C28 C24 C25 C31 4.1(5) . . . . ?
C28 C24 C25 N3 179.6(3) . . . . ?
C31 C25 N3 C26 171.7(2) . . . . ?
C31 C25 N3 B1 -21.9(4) . . . . ?
C31 C32 C33 C34 0.2(5) . . . . ?
C31 C32 C33 C37 -174.4(3) . . . . ?
C31 C32 N4 C47 171.2(3) . . . . ?
C31 C32 N4 B1 -14.7(4) . . . . ?
C32 C33 C34 C35 75.4(4) . . . . ?
C32 C33 C34 C36 -53.3(5) . . . . ?
C32 C33 C37 C38 -177.3(3) . . . . ?
C32 C33 C37 C47 4.3(3) . . . . ?
C33 C32 N4 C47 -3.3(3) . . . . ?
C33 C32 N4 B1 170.8(3) . . . . ?
C33 C37 C38 C39 20.3(5) . . . . ?
C33 C37 C38 C43 -163.3(3) . . . . ?
C33 C37 C47 C45 164.4(3) . . . . ?
C33 C37 C47 N4 -6.6(3) . . . . ?
C34 C33 C37 C38 8.3(6) . . . . ?
C34 C33 C37 C47 -170.1(3) . . . . ?
C37 C33 C34 C35 -111.1(4) . . . . ?
C37 C33 C34 C36 120.2(4) . . . . ?
C37 C38 C39 C40 -179.4(3) . . . . ?
C37 C38 C43 C42 179.7(3) . . . . ?
C37 C38 C43 C44 -3.4(5) . . . . ?
C37 C47 N4 C32 6.0(3) . . . . ?
C37 C47 N4 B1 -167.6(3) . . . . ?
C38 C37 C47 C45 -14.3(4) . . . . ?
C38 C37 C47 N4 174.7(2) . . . . ?
C38 C39 C40 C41 -1.7(6) . . . . ?
C38 C43 C44 C45 -9.0(5) . . . . ?
C38 C43 C44 C46 169.9(3) . . . . ?
C39 C38 C43 C42 -3.9(5) . . . . ?
C39 C38 C43 C44 173.1(3) . . . . ?
C39 C40 C41 C42 -1.0(7) . . . . ?
C40 C41 C42 C43 1.2(8) . . . . ?
C41 C42 C43 C38 1.3(6) . . . . ?
C41 C42 C43 C44 -175.5(4) . . . . ?
C42 C43 C44 C45 167.8(3) . . . . ?
C42 C43 C44 C46 -13.4(6) . . . . ?
C43 C38 C39 C40 4.2(5) . . . . ?
C43 C44 C45 C47 9.9(4) . . . . ?
C43 C44 C45 N5 -179.1(3) . . . . ?
C43 C44 C46 C48 -3.8(7) . . . . ?
C43 C44 C46 C48' 5(2) . . . . ?
C43 C44 C46 C51 -179.9(3) . . . . ?
C44 C45 C47 C37 1.7(4) . . . . ?
C44 C45 C47 N4 170.7(3) . . . . ?
C44 C45 N5 C51 -1.9(3) . . . . ?
C44 C46 C48 C49 -127.6(9) . . . . ?
C44 C46 C48 C50 96.2(8) . . . . ?
C44 C46 C48' C49' -80(5) . . . . ?
C44 C46 C48' C50' 134(4) . . . . ?
C44 C46 C51 C52 -179.4(3) . . . . ?
C44 C46 C51 N5 -0.2(4) . . . . ?
C45 C44 C46 C48 175.1(5) . . . . ?
C45 C44 C46 C48' -176(2) . . . . ?
C45 C44 C46 C51 -0.9(4) . . . . ?
C45 C47 N4 C32 -163.6(3) . . . . ?
C45 C47 N4 B1 22.7(5) . . . . ?
C46 C44 C45 C47 -169.2(3) . . . . ?
C46 C44 C45 N5 1.7(3) . . . . ?
C46 C51 C52 C53 -156.5(3) . . . . ?
C46 C51 N5 C45 1.3(3) . . . . ?
C47 C37 C38 C39 -161.4(3) . . . . ?
C47 C37 C38 C43 15.0(4) . . . . ?
C47 C45 N5 C51 168.2(3) . . . . ?
C48 C46 C51 C52 4.5(7) . . . . ?
C48 C46 C51 N5 -176.3(5) . . . . ?
C48' C46 C51 C52 -4(2) . . . . ?
C48' C46 C51 N5 175.4(19) . . . . ?
C51 C46 C48 C49 47.7(10) . . . . ?
C51 C46 C48 C50 -88.5(10) . . . . ?
C51 C46 C48' C49' 106(4) . . . . ?
C51 C46 C48' C50' -41(6) . . . . ?
C51 C52 C53 C54 90.0(4) . . . . ?
C51 C52 C53 N6 -87.2(4) . . . . ?
C52 C51 N5 C45 -179.3(3) . . . . ?
C52 C53 C54 C55 -177.0(3) . . . . ?
C52 C53 C54 C57 2.0(6) . . . . ?
C52 C53 N6 C56 177.0(2) . . . . ?
C53 C54 C55 C56 -0.1(3) . . . . ?
C53 C54 C55 C58 -179.9(3) . . . . ?
C54 C53 N6 C56 -0.8(3) . . . . ?
C54 C55 C56 C59 178.1(3) . . . . ?
C54 C55 C56 N6 -0.4(3) . . . . ?
C55 C56 C59 O3 178.8(3) . . . . ?
C55 C56 C59 O4 -2.5(5) . . . . ?
C55 C56 N6 C53 0.7(3) . . . . ?
C56 C59 O4 C60 -173.2(3) . . . . ?
C57 C54 C55 C56 -179.1(3) . . . . ?
C57 C54 C55 C58 1.1(6) . . . . ?
C58 C55 C56 C59 -2.1(6) . . . . ?
C58 C55 C56 N6 179.4(3) . . . . ?
C59 C56 N6 C53 -178.0(3) . . . . ?
C61 C60 O4 C59 176.5(5) . . . . ?
N1 C4 C5 C6 178.5(3) . . . . ?
N1 C4 C5 C8 -0.6(3) . . . . ?
N1 C9 C10 C11 -85.0(4) . . . . ?
N2 C11 C12 C13 -176.0(3) . . . . ?
N2 C11 C12 C16 1.1(3) . . . . ?
N3 C25 C31 C32 9.0(4) . . . . ?
N3 C26 C27 C16 173.4(3) . . . . ?
N3 C26 C27 N2 4.9(5) . . . . ?
N3 B1 N4 C32 3.2(4) . . . . ?
N3 B1 N4 C47 175.8(2) . . . . ?
N4 C32 C33 C34 173.9(3) . . . . ?
N4 C32 C33 C37 -0.8(3) . . . . ?
N4 B1 N3 C25 15.2(4) . . . . ?
N4 B1 N3 C26 178.5(2) . . . . ?
N5 C45 C47 C37 -167.2(3) . . . . ?
N5 C45 C47 N4 1.7(5) . . . . ?
N5 C51 C52 C53 24.4(4) . . . . ?
N6 C53 C54 C55 0.5(3) . . . . ?
N6 C53 C54 C57 179.6(3) . . . . ?
N6 C56 C59 O3 -2.9(5) . . . . ?
N6 C56 C59 O4 175.8(3) . . . . ?
O3 C59 O4 C60 5.6(5) . . . . ?
F1 B1 N3 C25 135.9(2) . . . . ?
F1 B1 N3 C26 -60.8(4) . . . . ?
F1 B1 N4 C32 -118.3(3) . . . . ?
F1 B1 N4 C47 54.3(4) . . . . ?
F2 B1 N3 C25 -105.4(3) . . . . ?
F2 B1 N3 C26 58.0(4) . . . . ?
F2 B1 N4 C32 123.6(3) . . . . ?
F2 B1 N4 C47 -63.8(4) . . . . ?
C63 C64 C65 C66 -140.4(19) . . . . ?
C64 C65 C66 C67 -71.5(17) . . . . ?
C65 C66 C67 C68 -67(2) . . . . ?
