#------------------------------------------------------------------------------
#$Date: 2024-11-09 14:07:10 +0200 (Sat, 09 Nov 2024) $
#$Revision: 295862 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/79/7247938.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_7247938
loop_
_publ_author_name
'Zhong, Jialing'
'Pan, Rihuang'
'Lin, Xufeng'
_publ_section_title
;
 Enantioselective synthesis of α-tetrasubstituted (1-indolizinyl)
 (diaryl)-methanamines via chiral phosphoric acid catalysis
;
_journal_issue                   2
_journal_name_full               'RSC Advances'
_journal_page_first              1106
_journal_page_last               1113
_journal_paper_doi               10.1039/D3RA07636A
_journal_volume                  14
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H19 Cl N2 O3, 1/3(C2 H6 O)'
_chemical_formula_sum            'C28.66667 H21 Cl N2 O3.33333'
_chemical_formula_weight         482.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2brz58
_audit_creation_date             2022-04-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-04-21 deposited with the CCDC.	2023-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 125.773(8)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   24.5506(14)
_cell_length_b                   14.4941(4)
_cell_length_c                   24.9660(13)
_cell_measurement_reflns_used    13715
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.3280
_cell_measurement_theta_min      1.8448
_cell_volume                     7207.8(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -52.00   26.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   96.0000  119.0000 78

#__ type_ start__ end____ width___ exp.time_
  2 omega  -86.00   15.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -38.0000  -60.0000 101

#__ type_ start__ end____ width___ exp.time_
  3 omega  -67.00   44.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808  -77.0000   30.0000 111

#__ type_ start__ end____ width___ exp.time_
  4 omega  -38.00   64.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   38.0000  -60.0000 102

#__ type_ start__ end____ width___ exp.time_
  5 omega  -22.00   90.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   77.0000  -90.0000 112

#__ type_ start__ end____ width___ exp.time_
  6 omega  -22.00   62.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   77.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
  7 omega  -37.00   15.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808  111.0000 -165.0000 52
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0189865000
_diffrn_orient_matrix_UB_12      0.0405707000
_diffrn_orient_matrix_UB_13      0.0156731000
_diffrn_orient_matrix_UB_21      -0.0301182000
_diffrn_orient_matrix_UB_22      0.0255316000
_diffrn_orient_matrix_UB_23      -0.0141207000
_diffrn_orient_matrix_UB_31      0.0002205000
_diffrn_orient_matrix_UB_32      -0.0098974000
_diffrn_orient_matrix_UB_33      0.0279526000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            63847
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.393
_diffrn_reflns_theta_min         1.849
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       needle
_exptl_crystal_F_000             3008
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 4049 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.039(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     951
_refine_ls_number_reflns         17756
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0516
_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)+(0.0593P)²+1.1635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1289
_reflns_Friedel_coverage         0.843
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.848
_reflns_number_gt                11396
_reflns_number_total             17756
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ra07636a2.cif
_cod_data_source_block           220420_zjl220420
_cod_depositor_comments
;

2024-11-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C86 H63 Cl3 N6 O10'
_cod_original_formula_weight         1446.77
_cod_original_formula_moiety         '3(C28 H19 Cl N2 O3), C2 H6 O'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        7207.8(8)
_cod_database_code               7247938
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C h n o cl'
_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   0.912
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C85(H85A,H85B)
2.b Aromatic/amide H refined with riding coordinates:
 N6(H6), N2(H2), C68(H68), C64(H64), C10(H10), C21(H21), C74(H74), N4(H4A),
 C8(H8), C36(H36), C73(H73), C4(H4), C25(H25), C77(H77), C1(H1), C20(H20),
 C35(H35), C76(H76), C29(H29), C3(H3), C7(H7), C63(H63), C60(H60), C26(H26),
 C59(H59), C58(H58), C57(H57), C38(H38), C17(H17), C27(H27), C32(H32), C18(H18),
  C2(H2A), C30(H30), C31(H31), C81(H81), C45(H45), C83(H83), C28(H28), C84(H84),
  C82(H82), C49(H49), C53(H53), C46(H46), C48(H48), C55(H55), C56(H56), C54(H54)
2.c Idealised Me refined as rotating group:
 C70(H70A,H70B,H70C), C14(H14A,H14B,H14C), C86(H86A,H86B,H86C), C42(H42A,H42B,
 H42C)
2.d Idealised tetrahedral OH refined as rotating group:
 O10(H10A)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.61498(7) 0.65506(10) 0.08490(6) 0.0917(4) Uani 1 1 d . . . . .
Cl3 Cl 0.96405(7) 0.28217(9) 0.68523(7) 0.0854(4) Uani 1 1 d . . . . .
Cl2 Cl 0.87055(10) 0.64688(13) 0.45029(9) 0.1287(7) Uani 1 1 d . . . . .
O8 O 0.88827(11) 0.53665(18) 0.81066(11) 0.0530(6) Uani 1 1 d . . . . .
N5 N 0.84490(13) 0.37830(18) 0.93600(12) 0.0403(6) Uani 1 1 d . . . . .
N1 N 0.24774(13) 0.55638(19) 0.04348(12) 0.0422(6) Uani 1 1 d . . . . .
O7 O 0.98122(13) 0.5031(2) 0.90934(13) 0.0706(8) Uani 1 1 d . . . . .
O3 O 0.44614(15) 0.22408(19) 0.16743(14) 0.0721(8) Uani 1 1 d . . . . .
O1 O 0.35802(15) 0.4007(2) -0.02589(13) 0.0710(8) Uani 1 1 d . . . . .
O2 O 0.26155(14) 0.4696(2) -0.10198(12) 0.0766(9) Uani 1 1 d . . . . .
N6 N 0.74574(14) 0.4856(2) 0.72821(13) 0.0513(7) Uani 1 1 d . . . . .
H6 H 0.768312 0.535539 0.736475 0.062 Uiso 1 1 calc R . . . .
N2 N 0.41755(14) 0.3585(2) 0.10881(14) 0.0507(7) Uani 1 1 d . . . . .
H2 H 0.400077 0.333271 0.070870 0.061 Uiso 1 1 calc R . . . .
N3 N 0.53755(16) 0.7497(2) 0.45238(14) 0.0547(8) Uani 1 1 d . . . . .
C67 C 0.87825(15) 0.4388(2) 0.87858(15) 0.0394(7) Uani 1 1 d . . . . .
C69 C 0.92198(16) 0.4943(2) 0.86888(15) 0.0440(7) Uani 1 1 d . . . . .
C12 C 0.34797(16) 0.4959(2) 0.07797(15) 0.0439(7) Uani 1 1 d . . . . .
C66 C 0.81401(15) 0.3990(2) 0.83239(15) 0.0397(7) Uani 1 1 d . . . . .
O9 O 0.64101(16) 0.5483(3) 0.65915(17) 0.0997(11) Uani 1 1 d . . . . .
C68 C 0.89552(16) 0.4244(2) 0.94064(15) 0.0408(7) Uani 1 1 d . . . . .
H68 H 0.935380 0.443031 0.979646 0.049 Uiso 1 1 calc R . . . .
C65 C 0.79326(15) 0.3625(2) 0.86907(15) 0.0412(7) Uani 1 1 d . . . . .
C71 C 0.77760(16) 0.3963(2) 0.75758(15) 0.0452(8) Uani 1 1 d . . . . .
C64 C 0.73397(18) 0.3175(3) 0.85476(19) 0.0526(9) Uani 1 1 d . . . . .
H64 H 0.697799 0.307833 0.811092 0.063 Uiso 1 1 calc R . . . .
O5 O 0.5892(2) 0.4795(2) 0.48750(17) 0.1033(12) Uani 1 1 d . . . . .
C33 C 0.47709(18) 0.7986(3) 0.41153(16) 0.0534(9) Uani 1 1 d . . . . .
C15 C 0.41947(17) 0.4589(2) 0.11721(16) 0.0464(8) Uani 1 1 d . . . . .
C9 C 0.31248(16) 0.5348(2) 0.09952(15) 0.0428(7) Uani 1 1 d . . . . .
C61 C 0.84221(17) 0.3487(2) 0.98806(16) 0.0449(8) Uani 1 1 d . . . . .
C5 C 0.19814(17) 0.6000(2) 0.04638(16) 0.0455(8) Uani 1 1 d . . . . .
C10 C 0.24305(17) 0.5298(2) -0.01110(16) 0.0483(8) Uani 1 1 d . . . . .
H10 H 0.205132 0.536001 -0.054328 0.058 Uiso 1 1 calc R . . . .
C11 C 0.30229(17) 0.4927(2) 0.00721(16) 0.0455(8) Uani 1 1 d . . . . .
C24 C 0.45887(16) 0.4637(3) 0.19272(16) 0.0482(8) Uani 1 1 d . . . . .
C23 C 0.47251(18) 0.3764(3) 0.21825(17) 0.0535(9) Uani 1 1 d . . . . .
C78 C 0.67779(19) 0.4828(3) 0.68696(18) 0.0641(11) Uani 1 1 d . . . . .
C72 C 0.82496(16) 0.3674(2) 0.73883(15) 0.0448(8) Uani 1 1 d . . . . .
C16 C 0.46297(17) 0.5067(3) 0.10005(16) 0.0481(8) Uani 1 1 d . . . . .
C21 C 0.45871(19) 0.6006(3) 0.09005(17) 0.0540(9) Uani 1 1 d . . . . .
H21 H 0.424550 0.633717 0.087002 0.065 Uiso 1 1 calc R . . . .
C13 C 0.31246(19) 0.4497(3) -0.03950(17) 0.0532(9) Uani 1 1 d . . . . .
O6 O 0.79226(19) 0.6989(4) 0.74044(14) 0.1165(15) Uani 1 1 d . . . . .
C37 C 0.60070(18) 0.7922(3) 0.49407(16) 0.0508(8) Uani 1 1 d . . . . .
C74 C 0.8617(2) 0.3791(3) 0.66822(17) 0.0570(9) Uani 1 1 d . . . . .
H74 H 0.858189 0.406385 0.632603 0.068 Uiso 1 1 calc R . . . .
N4 N 0.74669(19) 0.6781(3) 0.63158(15) 0.0780(11) Uani 1 1 d . . . . .
H4A H 0.741193 0.619407 0.631058 0.094 Uiso 1 1 calc R . . . .
C8 C 0.32592(18) 0.5571(3) 0.16213(16) 0.0498(8) Uani 1 1 d . . . . .
H8 H 0.367177 0.541167 0.200638 0.060 Uiso 1 1 calc R . . . .
C36 C 0.6013(2) 0.8896(3) 0.49776(18) 0.0580(9) Uani 1 1 d . . . . .
H36 H 0.641900 0.920268 0.525673 0.070 Uiso 1 1 calc R . . . .
C22 C 0.44480(18) 0.3085(3) 0.16413(18) 0.0549(9) Uani 1 1 d . . . . .
C73 C 0.81897(18) 0.4049(3) 0.68474(16) 0.0503(8) Uani 1 1 d . . . . .
H73 H 0.785582 0.448242 0.658920 0.060 Uiso 1 1 calc R . . . .
C62 C 0.78363(19) 0.3029(2) 0.97135(19) 0.0518(8) Uani 1 1 d . . . . .
C6 C 0.21482(18) 0.6238(2) 0.10844(17) 0.0493(8) Uani 1 1 d . . . . .
C75 C 0.9091(2) 0.3130(3) 0.70489(18) 0.0554(9) Uani 1 1 d . . . . .
C4 C 0.13494(18) 0.6201(3) -0.01075(18) 0.0544(9) Uani 1 1 d . . . . .
H4 H 0.123953 0.603370 -0.051934 0.065 Uiso 1 1 calc R . . . .
O4 O 0.6964(2) 0.5210(2) 0.5531(2) 0.1059(12) Uani 1 1 d . . . . .
C25 C 0.48359(18) 0.5405(3) 0.23371(18) 0.0592(9) Uani 1 1 d . . . . .
H25 H 0.475310 0.599847 0.216448 0.071 Uiso 1 1 calc R . . . .
C80 C 0.71708(18) 0.3332(3) 0.72281(16) 0.0530(9) Uani 1 1 d . . . . .
C43 C 0.7247(2) 0.7298(3) 0.57114(18) 0.0648(11) Uani 1 1 d . . . . .
C34 C 0.48028(19) 0.8951(3) 0.41678(17) 0.0543(9) Uani 1 1 d . . . . .
C77 C 0.87259(19) 0.2994(3) 0.77426(17) 0.0525(9) Uani 1 1 d . . . . .
H77 H 0.876363 0.271789 0.809915 0.063 Uiso 1 1 calc R . . . .
C1 C 0.1664(2) 0.6695(3) 0.1115(2) 0.0611(10) Uani 1 1 d . . . . .
H1 H 0.176371 0.686146 0.152359 0.073 Uiso 1 1 calc R . . . .
C20 C 0.5051(2) 0.6467(3) 0.08444(18) 0.0608(10) Uani 1 1 d . . . . .
H20 H 0.502363 0.710284 0.078323 0.073 Uiso 1 1 calc R . . . .
C35 C 0.5440(2) 0.9389(3) 0.46151(19) 0.0630(10) Uani 1 1 d . . . . .
H35 H 0.545824 1.002810 0.465662 0.076 Uiso 1 1 calc R . . . .
C76 C 0.9146(2) 0.2719(3) 0.75748(18) 0.0622(10) Uani 1 1 d . . . . .
H76 H 0.946360 0.225950 0.781532 0.075 Uiso 1 1 calc R . . . .
C29 C 0.4202(2) 0.9449(3) 0.37785(19) 0.0688(11) Uani 1 1 d . . . . .
H29 H 0.420859 1.008876 0.381215 0.083 Uiso 1 1 calc R . . . .
C41 C 0.6380(3) 0.5420(4) 0.5167(2) 0.0797(14) Uani 1 1 d . . . . .
C3 C 0.0892(2) 0.6649(3) -0.0054(2) 0.0623(10) Uani 1 1 d . . . . .
H3 H 0.046987 0.678772 -0.043460 0.075 Uiso 1 1 calc R . . . .
C44 C 0.7595(2) 0.6991(3) 0.53988(18) 0.0668(11) Uani 1 1 d . . . . .
C7 C 0.2805(2) 0.6002(3) 0.16644(17) 0.0542(9) Uani 1 1 d . . . . .
H7 H 0.291434 0.615333 0.207863 0.065 Uiso 1 1 calc R . . . .
C79 C 0.65953(19) 0.3843(3) 0.68372(17) 0.0643(11) Uani 1 1 d . . . . .
C63 C 0.73016(19) 0.2893(3) 0.9036(2) 0.0582(9) Uani 1 1 d . . . . .
H63 H 0.691327 0.259787 0.892833 0.070 Uiso 1 1 calc R . . . .
O10 O 0.5017(2) 1.1246(3) 0.28716(19) 0.1216(15) Uani 1 1 d . . . . .
H10A H 0.484039 1.151393 0.251725 0.182 Uiso 1 1 calc GR . . . .
C60 C 0.8948(2) 0.3640(3) 1.05361(17) 0.0563(9) Uani 1 1 d . . . . .
H60 H 0.933187 0.395101 1.064437 0.068 Uiso 1 1 calc R . . . .
C26 C 0.5211(2) 0.5256(4) 0.30125(19) 0.0709(12) Uani 1 1 d . . . . .
H26 H 0.537955 0.575872 0.329779 0.085 Uiso 1 1 calc R . . . .
C59 C 0.8895(3) 0.3325(3) 1.1026(2) 0.0727(12) Uani 1 1 d . . . . .
H59 H 0.925136 0.341119 1.146585 0.087 Uiso 1 1 calc R . . . .
C58 C 0.8331(3) 0.2891(3) 1.0876(2) 0.0750(12) Uani 1 1 d . . . . .
H58 H 0.830142 0.269450 1.121261 0.090 Uiso 1 1 calc R . . . .
C57 C 0.7812(2) 0.2745(3) 1.0236(2) 0.0676(11) Uani 1 1 d . . . . .
H57 H 0.742942 0.244710 1.014172 0.081 Uiso 1 1 calc R . . . .
C19 C 0.5545(2) 0.5976(3) 0.08803(19) 0.0643(11) Uani 1 1 d . . . . .
C52 C 0.7539(2) 0.8222(3) 0.6007(2) 0.0741(12) Uani 1 1 d . . . . .
C39 C 0.6128(2) 0.6369(3) 0.49975(19) 0.0664(11) Uani 1 1 d . . . . .
C38 C 0.5456(2) 0.6564(3) 0.45711(19) 0.0629(10) Uani 1 1 d . . . . .
H38 H 0.511195 0.613164 0.435131 0.076 Uiso 1 1 calc R . . . .
C17 C 0.5125(2) 0.4587(3) 0.1009(2) 0.0695(11) Uani 1 1 d . . . . .
H17 H 0.515145 0.394911 0.106000 0.083 Uiso 1 1 calc R . . . .
C27 C 0.5337(3) 0.4373(4) 0.3269(2) 0.0848(14) Uani 1 1 d . . . . .
H27 H 0.558479 0.428995 0.372370 0.102 Uiso 1 1 calc R . . . .
C32 C 0.4168(2) 0.7543(3) 0.3678(2) 0.0703(11) Uani 1 1 d . . . . .
H32 H 0.414997 0.690296 0.364215 0.084 Uiso 1 1 calc R . . . .
C18 C 0.5575(2) 0.5037(4) 0.0942(2) 0.0772(13) Uani 1 1 d . . . . .
H18 H 0.589757 0.470492 0.093921 0.093 Uiso 1 1 calc R . . . .
C2 C 0.1046(2) 0.6899(3) 0.0553(2) 0.0655(11) Uani 1 1 d . . . . .
H2A H 0.073022 0.720592 0.057970 0.079 Uiso 1 1 calc R . . . .
C40 C 0.6483(2) 0.7228(3) 0.52358(17) 0.0599(10) Uani 1 1 d . . . . .
C30 C 0.3609(2) 0.9009(4) 0.3353(2) 0.0809(14) Uani 1 1 d . . . . .
H30 H 0.321416 0.934723 0.309997 0.097 Uiso 1 1 calc R . . . .
C31 C 0.3592(2) 0.8069(4) 0.3294(2) 0.0782(13) Uani 1 1 d . . . . .
H31 H 0.318486 0.777837 0.298989 0.094 Uiso 1 1 calc R . . . .
C81 C 0.7134(2) 0.2388(3) 0.7262(2) 0.0693(11) Uani 1 1 d . . . . .
H81 H 0.752245 0.203416 0.750388 0.083 Uiso 1 1 calc R . . . .
C45 C 0.8231(2) 0.6615(4) 0.5771(2) 0.0867(15) Uani 1 1 d . . . . .
H45 H 0.843330 0.647946 0.621362 0.104 Uiso 1 1 calc R . . . .
C83 C 0.5938(3) 0.2497(6) 0.6561(3) 0.108(2) Uani 1 1 d . . . . .
H83 H 0.552260 0.220808 0.634593 0.130 Uiso 1 1 calc R . . . .
C28 C 0.5102(2) 0.3618(3) 0.2862(2) 0.0742(12) Uani 1 1 d . . . . .
H28 H 0.519166 0.302335 0.303412 0.089 Uiso 1 1 calc R . . . .
C84 C 0.5966(2) 0.3440(5) 0.6500(3) 0.0954(17) Uani 1 1 d . . . . .
H84 H 0.557717 0.378975 0.624167 0.114 Uiso 1 1 calc R . . . .
C70 C 0.9278(2) 0.5920(4) 0.7968(2) 0.0795(13) Uani 1 1 d . . . . .
H70A H 0.901343 0.606942 0.750658 0.119 Uiso 1 1 calc GR . . . .
H70B H 0.966843 0.557964 0.808397 0.119 Uiso 1 1 calc GR . . . .
H70C H 0.941464 0.647879 0.822234 0.119 Uiso 1 1 calc GR . . . .
C50 C 0.7750(2) 0.7261(4) 0.6859(2) 0.0827(14) Uani 1 1 d . . . . .
C82 C 0.6513(3) 0.1977(4) 0.6934(3) 0.0945(17) Uani 1 1 d . . . . .
H82 H 0.648123 0.134219 0.696374 0.113 Uiso 1 1 calc R . . . .
C51 C 0.7836(2) 0.8187(4) 0.6693(2) 0.0878(17) Uani 1 1 d . . . . .
C49 C 0.7301(2) 0.7170(3) 0.4739(2) 0.0733(12) Uani 1 1 d . . . . .
H49 H 0.686593 0.740172 0.447609 0.088 Uiso 1 1 calc R . . . .
C47 C 0.8274(3) 0.6651(3) 0.4849(2) 0.0833(14) Uani 1 1 d . . . . .
C53 C 0.7617(2) 0.9000(4) 0.5727(3) 0.0964(17) Uani 1 1 d . . . . .
H53 H 0.744165 0.901585 0.528072 0.116 Uiso 1 1 calc R . . . .
C46 C 0.8570(3) 0.6436(4) 0.5497(2) 0.0955(17) Uani 1 1 d . . . . .
H46 H 0.899543 0.617281 0.574981 0.115 Uiso 1 1 calc R . . . .
C48 C 0.7642(3) 0.7011(4) 0.4465(2) 0.0847(14) Uani 1 1 d . . . . .
H48 H 0.744379 0.714811 0.402350 0.102 Uiso 1 1 calc R . . . .
C14 C 0.2616(3) 0.4228(5) -0.1528(2) 0.1009(19) Uani 1 1 d . . . . .
H14A H 0.216561 0.419385 -0.192218 0.151 Uiso 1 1 calc GR . . . .
H14B H 0.279116 0.361528 -0.138265 0.151 Uiso 1 1 calc GR . . . .
H14C H 0.289200 0.456142 -0.161811 0.151 Uiso 1 1 calc GR . . . .
C55 C 0.8225(3) 0.9719(7) 0.6813(6) 0.146(4) Uani 1 1 d . . . . .
H55 H 0.843345 1.023678 0.707709 0.175 Uiso 1 1 calc R . . . .
C56 C 0.8171(3) 0.8931(7) 0.7079(4) 0.129(3) Uani 1 1 d . . . . .
H56 H 0.836588 0.890410 0.752961 0.155 Uiso 1 1 calc R . . . .
C85 C 0.4769(4) 1.0396(6) 0.2767(4) 0.134(3) Uani 1 1 d . . . . .
H85A H 0.477811 1.022211 0.314778 0.161 Uiso 1 1 calc R . . . .
H85B H 0.507263 0.998396 0.275489 0.161 Uiso 1 1 calc R . . . .
C54 C 0.7965(3) 0.9748(5) 0.6137(6) 0.140(3) Uani 1 1 d . . . . .
H54 H 0.802705 1.027352 0.596478 0.168 Uiso 1 1 calc R . . . .
C86 C 0.4120(5) 1.0225(7) 0.2202(4) 0.170(4) Uani 1 1 d . . . . .
H86A H 0.411771 1.027007 0.181743 0.256 Uiso 1 1 calc GR . . . .
H86B H 0.381506 1.067075 0.217436 0.256 Uiso 1 1 calc GR . . . .
H86C H 0.398193 0.961629 0.222773 0.256 Uiso 1 1 calc GR . . . .
C42 C 0.6112(4) 0.3845(4) 0.5053(3) 0.132(3) Uani 1 1 d . . . . .
H42A H 0.573247 0.344061 0.480108 0.198 Uiso 1 1 calc GR . . . .
H42B H 0.631765 0.375697 0.551507 0.198 Uiso 1 1 calc GR . . . .
H42C H 0.643170 0.370747 0.496000 0.198 Uiso 1 1 calc GR . . . .
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'
Cl Cl 0.1484 0.1585 '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'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D2RA03750E 2022
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
C69 O8 C70 116.2(3) . . ?
C68 N5 C65 109.1(2) . . ?
C68 N5 C61 127.4(3) . . ?
C65 N5 C61 123.5(3) . . ?
C9 N1 C5 123.7(3) . . ?
C10 N1 C9 108.6(3) . . ?
C10 N1 C5 127.6(3) . . ?
C13 O2 C14 116.3(3) . . ?
C71 N6 H6 122.8 . . ?
C78 N6 H6 122.8 . . ?
C78 N6 C71 114.4(3) . . ?
C15 N2 H2 122.2 . . ?
C22 N2 H2 122.2 . . ?
C22 N2 C15 115.7(3) . . ?
C33 N3 C37 123.7(3) . . ?
C38 N3 C33 127.0(3) . . ?
C38 N3 C37 109.3(3) . . ?
C66 C67 C69 131.2(3) . . ?
C68 C67 C69 120.0(3) . . ?
C68 C67 C66 108.7(3) . . ?
O8 C69 C67 112.6(3) . . ?
O7 C69 O8 123.0(3) . . ?
O7 C69 C67 124.3(3) . . ?
C9 C12 C15 130.1(3) . . ?
C9 C12 C11 106.0(3) . . ?
C11 C12 C15 123.9(3) . . ?
C67 C66 C71 125.5(3) . . ?
C65 C66 C67 106.3(3) . . ?
C65 C66 C71 128.2(3) . . ?
N5 C68 C67 108.6(3) . . ?
N5 C68 H68 125.7 . . ?
C67 C68 H68 125.7 . . ?
N5 C65 C64 116.6(3) . . ?
C66 C65 N5 107.4(3) . . ?
C66 C65 C64 136.0(3) . . ?
N6 C71 C66 110.4(3) . . ?
N6 C71 C72 111.3(3) . . ?
N6 C71 C80 100.9(3) . . ?
C66 C71 C72 111.8(3) . . ?
C80 C71 C66 113.2(3) . . ?
C80 C71 C72 108.8(3) . . ?
C65 C64 H64 119.6 . . ?
C63 C64 C65 120.8(3) . . ?
C63 C64 H64 119.6 . . ?
C41 O5 C42 115.1(5) . . ?
C34 C33 N3 117.2(3) . . ?
C32 C33 N3 121.8(4) . . ?
C32 C33 C34 120.9(4) . . ?
N2 C15 C12 109.2(3) . . ?
N2 C15 C24 99.5(3) . . ?
N2 C15 C16 112.2(3) . . ?
C12 C15 C24 115.8(3) . . ?
C12 C15 C16 113.1(3) . . ?
C16 C15 C24 106.4(3) . . ?
N1 C9 C8 116.1(3) . . ?
C12 C9 N1 107.8(3) . . ?
C12 C9 C8 136.1(3) . . ?
N5 C61 C62 117.5(3) . . ?
C60 C61 N5 121.8(3) . . ?
C60 C61 C62 120.7(3) . . ?
C6 C5 N1 117.8(3) . . ?
C4 C5 N1 121.3(3) . . ?
C4 C5 C6 120.9(3) . . ?
N1 C10 H10 125.4 . . ?
N1 C10 C11 109.3(3) . . ?
C11 C10 H10 125.4 . . ?
C12 C11 C13 128.2(3) . . ?
C10 C11 C12 108.3(3) . . ?
C10 C11 C13 123.3(3) . . ?
C23 C24 C15 109.7(3) . . ?
C23 C24 C25 121.0(3) . . ?
C25 C24 C15 129.1(3) . . ?
C24 C23 C22 109.5(3) . . ?
C24 C23 C28 121.1(4) . . ?
C28 C23 C22 129.4(4) . . ?
N6 C78 C79 105.6(3) . . ?
O9 C78 N6 125.9(5) . . ?
O9 C78 C79 128.5(4) . . ?
C73 C72 C71 121.4(3) . . ?
C73 C72 C77 118.2(3) . . ?
C77 C72 C71 120.3(3) . . ?
C21 C16 C15 120.5(3) . . ?
C21 C16 C17 118.1(3) . . ?
C17 C16 C15 121.1(3) . . ?
C16 C21 H21 119.6 . . ?
C16 C21 C20 120.7(4) . . ?
C20 C21 H21 119.6 . . ?
O1 C13 O2 122.6(3) . . ?
O1 C13 C11 126.4(3) . . ?
O2 C13 C11 111.0(3) . . ?
N3 C37 C36 116.7(3) . . ?
C40 C37 N3 107.3(3) . . ?
C40 C37 C36 135.9(4) . . ?
C73 C74 H74 120.4 . . ?
C75 C74 H74 120.4 . . ?
C75 C74 C73 119.1(3) . . ?
C43 N4 H4A 121.8 . . ?
C50 N4 H4A 121.8 . . ?
C50 N4 C43 116.5(4) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 C9 121.5(3) . . ?
C7 C8 H8 119.3 . . ?
C37 C36 H36 119.4 . . ?
C35 C36 C37 121.2(4) . . ?
C35 C36 H36 119.4 . . ?
O3 C22 N2 125.8(4) . . ?
O3 C22 C23 128.6(3) . . ?
N2 C22 C23 105.6(3) . . ?
C72 C73 C74 121.3(3) . . ?
C72 C73 H73 119.4 . . ?
C74 C73 H73 119.4 . . ?
C61 C62 C63 119.3(3) . . ?
C57 C62 C61 117.0(4) . . ?
C57 C62 C63 123.6(4) . . ?
C5 C6 C1 118.0(3) . . ?
C5 C6 C7 119.1(3) . . ?
C1 C6 C7 122.9(3) . . ?
C74 C75 Cl3 119.2(3) . . ?
C74 C75 C76 120.9(3) . . ?
C76 C75 Cl3 119.9(3) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 C5 119.1(4) . . ?
C3 C4 H4 120.5 . . ?
C24 C25 H25 121.1 . . ?
C26 C25 C24 117.7(4) . . ?
C26 C25 H25 121.1 . . ?
C79 C80 C71 109.8(3) . . ?
C79 C80 C81 120.2(4) . . ?
C81 C80 C71 130.1(4) . . ?
N4 C43 C44 113.3(3) . . ?
N4 C43 C52 99.6(3) . . ?
N4 C43 C40 108.1(3) . . ?
C44 C43 C40 112.6(3) . . ?
C52 C43 C44 105.3(4) . . ?
C52 C43 C40 117.4(3) . . ?
C33 C34 C35 119.4(3) . . ?
C29 C34 C33 118.0(4) . . ?
C29 C34 C35 122.6(4) . . ?
C72 C77 H77 119.5 . . ?
C76 C77 C72 121.0(3) . . ?
C76 C77 H77 119.5 . . ?
C6 C1 H1 119.6 . . ?
C2 C1 C6 120.8(4) . . ?
C2 C1 H1 119.6 . . ?
C21 C20 H20 120.3 . . ?
C19 C20 C21 119.3(4) . . ?
C19 C20 H20 120.3 . . ?
C36 C35 C34 121.6(4) . . ?
C36 C35 H35 119.2 . . ?
C34 C35 H35 119.2 . . ?
C75 C76 C77 119.4(4) . . ?
C75 C76 H76 120.3 . . ?
C77 C76 H76 120.3 . . ?
C34 C29 H29 119.6 . . ?
C30 C29 C34 120.8(5) . . ?
C30 C29 H29 119.6 . . ?
O5 C41 C39 112.9(5) . . ?
O4 C41 O5 122.4(5) . . ?
O4 C41 C39 124.7(5) . . ?
C4 C3 H3 119.4 . . ?
C4 C3 C2 121.1(4) . . ?
C2 C3 H3 119.4 . . ?
C45 C44 C43 121.6(3) . . ?
C45 C44 C49 118.3(4) . . ?
C49 C44 C43 119.8(4) . . ?
C8 C7 C6 121.7(3) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C80 C79 C78 109.1(3) . . ?
C80 C79 C84 121.5(5) . . ?
C84 C79 C78 129.3(5) . . ?
C64 C63 C62 122.2(3) . . ?
C64 C63 H63 118.9 . . ?
C62 C63 H63 118.9 . . ?
C85 O10 H10A 109.5 . . ?
C61 C60 H60 120.5 . . ?
C59 C60 C61 119.1(4) . . ?
C59 C60 H60 120.5 . . ?
C25 C26 H26 119.4 . . ?
C27 C26 C25 121.1(4) . . ?
C27 C26 H26 119.4 . . ?
C60 C59 H59 119.4 . . ?
C58 C59 C60 121.2(4) . . ?
C58 C59 H59 119.4 . . ?
C59 C58 H58 120.0 . . ?
C57 C58 C59 120.1(4) . . ?
C57 C58 H58 120.0 . . ?
C62 C57 H57 119.1 . . ?
C58 C57 C62 121.8(4) . . ?
C58 C57 H57 119.1 . . ?
C20 C19 Cl1 119.7(4) . . ?
C20 C19 C18 121.0(4) . . ?
C18 C19 Cl1 119.3(4) . . ?
C51 C52 C43 108.9(5) . . ?
C53 C52 C43 129.9(5) . . ?
C53 C52 C51 120.7(5) . . ?
C38 C39 C41 122.0(5) . . ?
C38 C39 C40 107.8(4) . . ?
C40 C39 C41 130.1(4) . . ?
N3 C38 C39 108.6(4) . . ?
N3 C38 H38 125.7 . . ?
C39 C38 H38 125.7 . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.2(4) . . ?
C18 C17 H17 119.4 . . ?
C26 C27 H27 119.6 . . ?
C28 C27 C26 120.8(4) . . ?
C28 C27 H27 119.6 . . ?
C33 C32 H32 120.7 . . ?
C33 C32 C31 118.7(5) . . ?
C31 C32 H32 120.7 . . ?
C19 C18 C17 119.4(4) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C1 C2 C3 120.0(4) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C37 C40 C43 129.6(4) . . ?
C37 C40 C39 106.9(4) . . ?
C39 C40 C43 123.5(4) . . ?
C29 C30 H30 119.8 . . ?
C29 C30 C31 120.3(5) . . ?
C31 C30 H30 119.8 . . ?
C32 C31 H31 119.4 . . ?
C30 C31 C32 121.2(5) . . ?
C30 C31 H31 119.4 . . ?
C80 C81 H81 120.5 . . ?
C82 C81 C80 119.0(5) . . ?
C82 C81 H81 120.5 . . ?
C44 C45 H45 119.5 . . ?
C46 C45 C44 121.0(4) . . ?
C46 C45 H45 119.5 . . ?
C84 C83 H83 119.3 . . ?
C82 C83 H83 119.3 . . ?
C82 C83 C84 121.3(5) . . ?
C23 C28 H28 120.9 . . ?
C27 C28 C23 118.3(4) . . ?
C27 C28 H28 120.9 . . ?
C79 C84 H84 121.3 . . ?
C83 C84 C79 117.4(6) . . ?
C83 C84 H84 121.3 . . ?
O8 C70 H70A 109.5 . . ?
O8 C70 H70B 109.5 . . ?
O8 C70 H70C 109.5 . . ?
H70A C70 H70B 109.5 . . ?
H70A C70 H70C 109.5 . . ?
H70B C70 H70C 109.5 . . ?
O6 C50 N4 127.5(6) . . ?
O6 C50 C51 126.6(5) . . ?
N4 C50 C51 105.9(4) . . ?
C81 C82 H82 119.8 . . ?
C83 C82 C81 120.5(6) . . ?
C83 C82 H82 119.8 . . ?
C52 C51 C50 108.6(4) . . ?
C56 C51 C52 120.0(7) . . ?
C56 C51 C50 131.3(6) . . ?
C44 C49 H49 119.5 . . ?
C48 C49 C44 121.1(4) . . ?
C48 C49 H49 119.5 . . ?
C46 C47 Cl2 119.9(4) . . ?
C48 C47 Cl2 118.9(4) . . ?
C48 C47 C46 121.2(4) . . ?
C52 C53 H53 121.2 . . ?
C54 C53 C52 117.7(7) . . ?
C54 C53 H53 121.2 . . ?
C45 C46 H46 120.4 . . ?
C47 C46 C45 119.2(4) . . ?
C47 C46 H46 120.4 . . ?
C49 C48 H48 120.4 . . ?
C47 C48 C49 119.2(4) . . ?
C47 C48 H48 120.4 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C56 C55 H55 120.0 . . ?
C56 C55 C54 120.1(7) . . ?
C54 C55 H55 120.0 . . ?
C51 C56 C55 120.7(8) . . ?
C51 C56 H56 119.7 . . ?
C55 C56 H56 119.7 . . ?
O10 C85 H85A 107.6 . . ?
O10 C85 H85B 107.6 . . ?
O10 C85 C86 118.8(7) . . ?
H85A C85 H85B 107.0 . . ?
C86 C85 H85A 107.6 . . ?
C86 C85 H85B 107.6 . . ?
C53 C54 C55 120.7(8) . . ?
C53 C54 H54 119.6 . . ?
C55 C54 H54 119.6 . . ?
C85 C86 H86A 109.5 . . ?
C85 C86 H86B 109.5 . . ?
C85 C86 H86C 109.5 . . ?
H86A C86 H86B 109.5 . . ?
H86A C86 H86C 109.5 . . ?
H86B C86 H86C 109.5 . . ?
O5 C42 H42A 109.5 . . ?
O5 C42 H42B 109.5 . . ?
O5 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 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
Cl1 C19 1.744(4) . ?
Cl3 C75 1.742(4) . ?
Cl2 C47 1.735(5) . ?
O8 C69 1.330(4) . ?
O8 C70 1.449(5) . ?
N5 C68 1.355(4) . ?
N5 C65 1.405(4) . ?
N5 C61 1.406(4) . ?
N1 C9 1.407(4) . ?
N1 C5 1.411(4) . ?
N1 C10 1.355(4) . ?
O7 C69 1.198(4) . ?
O3 C22 1.226(5) . ?
O1 C13 1.195(4) . ?
O2 C13 1.341(4) . ?
O2 C14 1.439(5) . ?
N6 H6 0.8600 . ?
N6 C71 1.468(4) . ?
N6 C78 1.355(5) . ?
N2 H2 0.8600 . ?
N2 C15 1.468(5) . ?
N2 C22 1.341(5) . ?
N3 C33 1.406(5) . ?
N3 C37 1.407(5) . ?
N3 C38 1.362(5) . ?
C67 C69 1.470(5) . ?
C67 C66 1.422(4) . ?
C67 C68 1.362(4) . ?
C12 C15 1.522(5) . ?
C12 C9 1.384(5) . ?
C12 C11 1.437(4) . ?
C66 C65 1.387(4) . ?
C66 C71 1.529(4) . ?
O9 C78 1.211(5) . ?
C68 H68 0.9300 . ?
C65 C64 1.437(5) . ?
C71 C72 1.544(5) . ?
C71 C80 1.514(5) . ?
C64 H64 0.9300 . ?
C64 C63 1.339(5) . ?
O5 C41 1.328(7) . ?
O5 C42 1.452(6) . ?
C33 C34 1.403(6) . ?
C33 C32 1.380(6) . ?
C15 C24 1.537(5) . ?
C15 C16 1.529(5) . ?
C9 C8 1.433(5) . ?
C61 C62 1.407(5) . ?
C61 C60 1.387(5) . ?
C5 C6 1.395(5) . ?
C5 C4 1.393(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.355(5) . ?
C11 C13 1.466(5) . ?
C24 C23 1.367(5) . ?
C24 C25 1.389(5) . ?
C23 C22 1.477(5) . ?
C23 C28 1.394(5) . ?
C78 C79 1.485(7) . ?
C72 C73 1.381(5) . ?
C72 C77 1.383(5) . ?
C16 C21 1.377(5) . ?
C16 C17 1.390(5) . ?
C21 H21 0.9300 . ?
C21 C20 1.397(5) . ?
O6 C50 1.231(6) . ?
C37 C36 1.414(5) . ?
C37 C40 1.384(5) . ?
C74 H74 0.9300 . ?
C74 C73 1.385(5) . ?
C74 C75 1.365(5) . ?
N4 H4A 0.8600 . ?
N4 C43 1.476(5) . ?
N4 C50 1.305(6) . ?
C8 H8 0.9300 . ?
C8 C7 1.337(5) . ?
C36 H36 0.9300 . ?
C36 C35 1.349(6) . ?
C73 H73 0.9300 . ?
C62 C63 1.424(6) . ?
C62 C57 1.403(5) . ?
C6 C1 1.403(5) . ?
C6 C7 1.443(5) . ?
C75 C76 1.375(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.369(5) . ?
O4 C41 1.205(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.387(5) . ?
C80 C79 1.373(5) . ?
C80 C81 1.377(6) . ?
C43 C44 1.523(6) . ?
C43 C52 1.495(7) . ?
C43 C40 1.527(6) . ?
C34 C35 1.433(6) . ?
C34 C29 1.402(5) . ?
C77 H77 0.9300 . ?
C77 C76 1.379(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.367(6) . ?
C20 H20 0.9300 . ?
C20 C19 1.362(6) . ?
C35 H35 0.9300 . ?
C76 H76 0.9300 . ?
C29 H29 0.9300 . ?
C29 C30 1.358(7) . ?
C41 C39 1.465(6) . ?
C3 H3 0.9300 . ?
C3 C2 1.379(6) . ?
C44 C45 1.379(6) . ?
C44 C49 1.383(5) . ?
C7 H7 0.9300 . ?
C79 C84 1.384(7) . ?
C63 H63 0.9300 . ?
O10 H10A 0.8200 . ?
O10 C85 1.332(8) . ?
C60 H60 0.9300 . ?
C60 C59 1.381(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.384(7) . ?
C59 H59 0.9300 . ?
C59 C58 1.358(7) . ?
C58 H58 0.9300 . ?
C58 C57 1.357(6) . ?
C57 H57 0.9300 . ?
C19 C18 1.368(6) . ?
C52 C51 1.417(7) . ?
C52 C53 1.398(8) . ?
C39 C38 1.373(6) . ?
C39 C40 1.435(6) . ?
C38 H38 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.375(6) . ?
C27 H27 0.9300 . ?
C27 C28 1.370(7) . ?
C32 H32 0.9300 . ?
C32 C31 1.386(7) . ?
C18 H18 0.9300 . ?
C2 H2A 0.9300 . ?
C30 H30 0.9300 . ?
C30 C31 1.367(7) . ?
C31 H31 0.9300 . ?
C81 H81 0.9300 . ?
C81 C82 1.374(7) . ?
C45 H45 0.9300 . ?
C45 C46 1.376(7) . ?
C83 H83 0.9300 . ?
C83 C84 1.381(9) . ?
C83 C82 1.374(9) . ?
C28 H28 0.9300 . ?
C84 H84 0.9300 . ?
C70 H70A 0.9600 . ?
C70 H70B 0.9600 . ?
C70 H70C 0.9600 . ?
C50 C51 1.456(8) . ?
C82 H82 0.9300 . ?
C51 C56 1.357(9) . ?
C49 H49 0.9300 . ?
C49 C48 1.374(6) . ?
C47 C46 1.366(6) . ?
C47 C48 1.364(7) . ?
C53 H53 0.9300 . ?
C53 C54 1.390(10) . ?
C46 H46 0.9300 . ?
C48 H48 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C55 H55 0.9300 . ?
C55 C56 1.367(12) . ?
C55 C54 1.414(12) . ?
C56 H56 0.9300 . ?
C85 H85A 0.9700 . ?
C85 H85B 0.9700 . ?
C85 C86 1.400(10) . ?
C54 H54 0.9300 . ?
C86 H86A 0.9600 . ?
C86 H86B 0.9600 . ?
C86 H86C 0.9600 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
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
Cl1 C19 C18 C17 175.9(3) . . . . ?
Cl3 C75 C76 C77 177.5(3) . . . . ?
Cl2 C47 C46 C45 177.7(5) . . . . ?
Cl2 C47 C48 C49 -179.0(4) . . . . ?
N5 C65 C64 C63 -2.5(5) . . . . ?
N5 C61 C62 C63 -0.5(5) . . . . ?
N5 C61 C62 C57 -179.4(3) . . . . ?
N5 C61 C60 C59 -179.4(3) . . . . ?
N1 C9 C8 C7 -3.4(5) . . . . ?
N1 C5 C6 C1 178.3(3) . . . . ?
N1 C5 C6 C7 -2.1(5) . . . . ?
N1 C5 C4 C3 -178.1(3) . . . . ?
N1 C10 C11 C12 -0.2(4) . . . . ?
N1 C10 C11 C13 174.6(3) . . . . ?
N6 C71 C72 C73 -20.3(4) . . . . ?
N6 C71 C72 C77 163.0(3) . . . . ?
N6 C71 C80 C79 -4.4(4) . . . . ?
N6 C71 C80 C81 176.5(4) . . . . ?
N6 C78 C79 C80 -0.1(4) . . . . ?
N6 C78 C79 C84 178.1(4) . . . . ?
N2 C15 C24 C23 -2.0(3) . . . . ?
N2 C15 C24 C25 173.3(4) . . . . ?
N2 C15 C16 C21 164.9(3) . . . . ?
N2 C15 C16 C17 -21.9(4) . . . . ?
N3 C33 C34 C35 1.5(5) . . . . ?
N3 C33 C34 C29 -178.1(3) . . . . ?
N3 C33 C32 C31 179.6(4) . . . . ?
N3 C37 C36 C35 -1.7(5) . . . . ?
N3 C37 C40 C43 177.6(3) . . . . ?
N3 C37 C40 C39 -0.8(4) . . . . ?
C67 C66 C65 N5 -1.3(3) . . . . ?
C67 C66 C65 C64 176.6(4) . . . . ?
C67 C66 C71 N6 -79.5(4) . . . . ?
C67 C66 C71 C72 45.0(4) . . . . ?
C67 C66 C71 C80 168.3(3) . . . . ?
C69 C67 C66 C65 -173.8(3) . . . . ?
C69 C67 C66 C71 7.7(5) . . . . ?
C69 C67 C68 N5 175.0(3) . . . . ?
C12 C15 C24 C23 114.8(3) . . . . ?
C12 C15 C24 C25 -69.9(5) . . . . ?
C12 C15 C16 C21 40.8(4) . . . . ?
C12 C15 C16 C17 -145.9(3) . . . . ?
C12 C9 C8 C7 176.4(4) . . . . ?
C12 C11 C13 O1 9.2(6) . . . . ?
C12 C11 C13 O2 -173.2(3) . . . . ?
C66 C67 C69 O8 23.1(5) . . . . ?
C66 C67 C69 O7 -159.0(4) . . . . ?
C66 C67 C68 N5 -0.7(4) . . . . ?
C66 C65 C64 C63 179.6(4) . . . . ?
C66 C71 C72 C73 -144.2(3) . . . . ?
C66 C71 C72 C77 39.1(4) . . . . ?
C66 C71 C80 C79 113.5(3) . . . . ?
C66 C71 C80 C81 -65.6(5) . . . . ?
O9 C78 C79 C80 179.7(4) . . . . ?
O9 C78 C79 C84 -2.0(8) . . . . ?
C68 N5 C65 C66 0.9(3) . . . . ?
C68 N5 C65 C64 -177.5(3) . . . . ?
C68 N5 C61 C62 179.1(3) . . . . ?
C68 N5 C61 C60 -0.6(5) . . . . ?
C68 C67 C69 O8 -151.5(3) . . . . ?
C68 C67 C69 O7 26.4(5) . . . . ?
C68 C67 C66 C65 1.3(4) . . . . ?
C68 C67 C66 C71 -177.2(3) . . . . ?
C65 N5 C68 C67 -0.1(3) . . . . ?
C65 N5 C61 C62 -1.6(4) . . . . ?
C65 N5 C61 C60 178.7(3) . . . . ?
C65 C66 C71 N6 102.3(4) . . . . ?
C65 C66 C71 C72 -133.2(3) . . . . ?
C65 C66 C71 C80 -9.9(5) . . . . ?
C65 C64 C63 C62 0.6(6) . . . . ?
C71 N6 C78 O9 177.2(4) . . . . ?
C71 N6 C78 C79 -2.9(4) . . . . ?
C71 C66 C65 N5 177.1(3) . . . . ?
C71 C66 C65 C64 -4.9(6) . . . . ?
C71 C72 C73 C74 179.7(3) . . . . ?
C71 C72 C77 C76 179.1(4) . . . . ?
C71 C80 C79 C78 3.0(4) . . . . ?
C71 C80 C79 C84 -175.5(4) . . . . ?
C71 C80 C81 C82 175.0(4) . . . . ?
O5 C41 C39 C38 -1.0(6) . . . . ?
O5 C41 C39 C40 175.9(4) . . . . ?
C33 N3 C37 C36 4.9(5) . . . . ?
C33 N3 C37 C40 -176.8(3) . . . . ?
C33 N3 C38 C39 176.6(3) . . . . ?
C33 C34 C35 C36 1.5(6) . . . . ?
C33 C34 C29 C30 -1.5(6) . . . . ?
C33 C32 C31 C30 -1.5(7) . . . . ?
C15 N2 C22 O3 177.3(4) . . . . ?
C15 N2 C22 C23 -3.4(4) . . . . ?
C15 C12 C9 N1 -179.1(3) . . . . ?
C15 C12 C9 C8 1.1(6) . . . . ?
C15 C12 C11 C10 178.9(3) . . . . ?
C15 C12 C11 C13 4.5(6) . . . . ?
C15 C24 C23 C22 0.3(4) . . . . ?
C15 C24 C23 C28 177.4(4) . . . . ?
C15 C24 C25 C26 -176.5(4) . . . . ?
C15 C16 C21 C20 170.1(3) . . . . ?
C15 C16 C17 C18 -171.2(4) . . . . ?
C9 N1 C5 C6 0.7(4) . . . . ?
C9 N1 C5 C4 179.7(3) . . . . ?
C9 N1 C10 C11 -0.6(4) . . . . ?
C9 C12 C15 N2 112.2(4) . . . . ?
C9 C12 C15 C24 1.0(5) . . . . ?
C9 C12 C15 C16 -122.1(4) . . . . ?
C9 C12 C11 C10 0.9(4) . . . . ?
C9 C12 C11 C13 -173.5(3) . . . . ?
C9 C8 C7 C6 2.1(6) . . . . ?
C61 N5 C68 C67 179.3(3) . . . . ?
C61 N5 C65 C66 -178.5(3) . . . . ?
C61 N5 C65 C64 3.1(4) . . . . ?
C61 C62 C63 C64 0.9(6) . . . . ?
C61 C62 C57 C58 -0.8(6) . . . . ?
C61 C60 C59 C58 -1.8(6) . . . . ?
C5 N1 C9 C12 -177.8(3) . . . . ?
C5 N1 C9 C8 2.0(4) . . . . ?
C5 N1 C10 C11 178.4(3) . . . . ?
C5 C6 C1 C2 0.1(5) . . . . ?
C5 C6 C7 C8 0.8(5) . . . . ?
C5 C4 C3 C2 -0.3(6) . . . . ?
C10 N1 C9 C12 1.1(4) . . . . ?
C10 N1 C9 C8 -179.0(3) . . . . ?
C10 N1 C5 C6 -178.1(3) . . . . ?
C10 N1 C5 C4 0.9(5) . . . . ?
C10 C11 C13 O1 -164.4(4) . . . . ?
C10 C11 C13 O2 13.2(5) . . . . ?
C11 C12 C15 N2 -65.3(4) . . . . ?
C11 C12 C15 C24 -176.5(3) . . . . ?
C11 C12 C15 C16 60.4(4) . . . . ?
C11 C12 C9 N1 -1.2(3) . . . . ?
C11 C12 C9 C8 179.0(4) . . . . ?
C24 C15 C16 C21 -87.4(4) . . . . ?
C24 C15 C16 C17 85.9(4) . . . . ?
C24 C23 C22 O3 -178.9(4) . . . . ?
C24 C23 C22 N2 1.8(4) . . . . ?
C24 C23 C28 C27 -0.4(6) . . . . ?
C24 C25 C26 C27 0.4(6) . . . . ?
C23 C24 C25 C26 -1.7(5) . . . . ?
C78 N6 C71 C66 -115.4(3) . . . . ?
C78 N6 C71 C72 119.8(3) . . . . ?
C78 N6 C71 C80 4.5(4) . . . . ?
C78 C79 C84 C83 -179.3(4) . . . . ?
C72 C71 C80 C79 -121.5(3) . . . . ?
C72 C71 C80 C81 59.3(5) . . . . ?
C72 C77 C76 C75 0.2(6) . . . . ?
C16 C15 C24 C23 -118.7(3) . . . . ?
C16 C15 C24 C25 56.6(5) . . . . ?
C16 C21 C20 C19 0.9(5) . . . . ?
C16 C17 C18 C19 1.3(7) . . . . ?
C21 C16 C17 C18 2.2(6) . . . . ?
C21 C20 C19 Cl1 -177.1(3) . . . . ?
C21 C20 C19 C18 2.8(6) . . . . ?
O6 C50 C51 C52 -177.2(4) . . . . ?
O6 C50 C51 C56 7.7(9) . . . . ?
C37 N3 C33 C34 -4.7(5) . . . . ?
C37 N3 C33 C32 175.2(3) . . . . ?
C37 N3 C38 C39 -1.5(4) . . . . ?
C37 C36 C35 C34 -1.3(6) . . . . ?
C74 C75 C76 C77 -1.5(6) . . . . ?
N4 C43 C44 C45 -27.9(7) . . . . ?
N4 C43 C44 C49 158.4(4) . . . . ?
N4 C43 C52 C51 -4.0(4) . . . . ?
N4 C43 C52 C53 167.8(5) . . . . ?
N4 C43 C40 C37 123.7(4) . . . . ?
N4 C43 C40 C39 -58.2(5) . . . . ?
N4 C50 C51 C52 4.2(5) . . . . ?
N4 C50 C51 C56 -171.0(5) . . . . ?
C36 C37 C40 C43 -4.5(7) . . . . ?
C36 C37 C40 C39 177.1(4) . . . . ?
C22 N2 C15 C12 -118.3(3) . . . . ?
C22 N2 C15 C24 3.4(4) . . . . ?
C22 N2 C15 C16 115.5(3) . . . . ?
C22 C23 C28 C27 176.1(4) . . . . ?
C73 C72 C77 C76 2.2(5) . . . . ?
C73 C74 C75 Cl3 -178.7(3) . . . . ?
C73 C74 C75 C76 0.3(6) . . . . ?
C62 C61 C60 C59 1.0(5) . . . . ?
C6 C5 C4 C3 0.8(5) . . . . ?
C6 C1 C2 C3 0.4(6) . . . . ?
C75 C74 C73 C72 2.3(6) . . . . ?
C4 C5 C6 C1 -0.7(5) . . . . ?
C4 C5 C6 C7 178.9(3) . . . . ?
C4 C3 C2 C1 -0.3(6) . . . . ?
O4 C41 C39 C38 179.0(4) . . . . ?
O4 C41 C39 C40 -4.2(7) . . . . ?
C25 C24 C23 C22 -175.5(3) . . . . ?
C25 C24 C23 C28 1.7(6) . . . . ?
C25 C26 C27 C28 0.8(7) . . . . ?
C80 C71 C72 C73 90.1(4) . . . . ?
C80 C71 C72 C77 -86.7(4) . . . . ?
C80 C79 C84 C83 -1.2(7) . . . . ?
C80 C81 C82 C83 1.9(7) . . . . ?
C43 N4 C50 O6 173.9(4) . . . . ?
C43 N4 C50 C51 -7.4(5) . . . . ?
C43 C44 C45 C46 -172.6(5) . . . . ?
C43 C44 C49 C48 171.4(5) . . . . ?
C43 C52 C51 C50 0.3(5) . . . . ?
C43 C52 C51 C56 176.1(5) . . . . ?
C43 C52 C53 C54 -174.1(5) . . . . ?
C34 C33 C32 C31 -0.5(6) . . . . ?
C34 C29 C30 C31 -0.5(7) . . . . ?
C77 C72 C73 C74 -3.5(5) . . . . ?
C1 C6 C7 C8 -179.6(4) . . . . ?
C20 C19 C18 C17 -3.9(7) . . . . ?
C35 C34 C29 C30 179.0(4) . . . . ?
C29 C34 C35 C36 -179.0(4) . . . . ?
C29 C30 C31 C32 2.1(7) . . . . ?
C41 C39 C38 N3 178.5(3) . . . . ?
C41 C39 C40 C37 -177.3(4) . . . . ?
C41 C39 C40 C43 4.2(6) . . . . ?
C44 C43 C52 C51 -121.6(4) . . . . ?
C44 C43 C52 C53 50.3(6) . . . . ?
C44 C43 C40 C37 -110.4(5) . . . . ?
C44 C43 C40 C39 67.8(5) . . . . ?
C44 C45 C46 C47 1.1(9) . . . . ?
C44 C49 C48 C47 1.6(8) . . . . ?
C7 C6 C1 C2 -179.5(4) . . . . ?
C79 C80 C81 C82 -4.1(6) . . . . ?
C63 C62 C57 C58 -179.7(4) . . . . ?
C60 C61 C62 C63 179.2(3) . . . . ?
C60 C61 C62 C57 0.3(5) . . . . ?
C60 C59 C58 C57 1.3(7) . . . . ?
C26 C27 C28 C23 -0.8(7) . . . . ?
C59 C58 C57 C62 0.1(7) . . . . ?
C57 C62 C63 C64 179.8(4) . . . . ?
C52 C43 C44 C45 79.9(5) . . . . ?
C52 C43 C44 C49 -93.7(5) . . . . ?
C52 C43 C40 C37 12.1(6) . . . . ?
C52 C43 C40 C39 -169.7(4) . . . . ?
C52 C51 C56 C55 0.2(9) . . . . ?
C52 C53 C54 C55 -0.4(8) . . . . ?
C38 N3 C33 C34 177.4(3) . . . . ?
C38 N3 C33 C32 -2.8(5) . . . . ?
C38 N3 C37 C36 -176.9(3) . . . . ?
C38 N3 C37 C40 1.5(4) . . . . ?
C38 C39 C40 C37 -0.1(4) . . . . ?
C38 C39 C40 C43 -178.6(3) . . . . ?
C17 C16 C21 C20 -3.4(5) . . . . ?
C32 C33 C34 C35 -178.4(3) . . . . ?
C32 C33 C34 C29 2.0(5) . . . . ?
C40 C37 C36 C35 -179.5(4) . . . . ?
C40 C43 C44 C45 -151.0(5) . . . . ?
C40 C43 C44 C49 35.3(6) . . . . ?
C40 C43 C52 C51 112.3(4) . . . . ?
C40 C43 C52 C53 -75.9(6) . . . . ?
C40 C39 C38 N3 1.0(4) . . . . ?
C81 C80 C79 C78 -177.8(3) . . . . ?
C81 C80 C79 C84 3.8(6) . . . . ?
C45 C44 C49 C48 -2.5(8) . . . . ?
C28 C23 C22 O3 4.3(7) . . . . ?
C28 C23 C22 N2 -175.1(4) . . . . ?
C84 C83 C82 C81 0.7(8) . . . . ?
C70 O8 C69 O7 2.7(5) . . . . ?
C70 O8 C69 C67 -179.3(3) . . . . ?
C50 N4 C43 C44 118.7(4) . . . . ?
C50 N4 C43 C52 7.3(5) . . . . ?
C50 N4 C43 C40 -115.8(4) . . . . ?
C50 C51 C56 C55 174.8(6) . . . . ?
C82 C83 C84 C79 -1.1(8) . . . . ?
C51 C52 C53 C54 -3.1(7) . . . . ?
C49 C44 C45 C46 1.1(8) . . . . ?
C53 C52 C51 C50 -172.4(4) . . . . ?
C53 C52 C51 C56 3.3(7) . . . . ?
C46 C47 C48 C49 0.7(8) . . . . ?
C48 C47 C46 C45 -2.0(9) . . . . ?
C14 O2 C13 O1 4.7(6) . . . . ?
C14 O2 C13 C11 -173.0(4) . . . . ?
C56 C55 C54 C53 3.9(10) . . . . ?
C54 C55 C56 C51 -3.7(11) . . . . ?
C42 O5 C41 O4 3.0(7) . . . . ?
C42 O5 C41 C39 -177.0(4) . . . . ?
