#------------------------------------------------------------------------------
#$Date: 2020-08-13 02:15:25 +0300 (Thu, 13 Aug 2020) $
#$Revision: 255267 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/86/4038681.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_4038681
loop_
_publ_author_name
'Mądry, Tomasz'
'Czapik, Agnieszka'
'Kwit, Marcin'
_publ_section_title
;
 Point-to-Axial Chirality Transmission: A Highly Sensitive Triaryl
 Chirality Probe for Stereochemical Assignments of Amines
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00734
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C38 H44 N2'
_chemical_formula_sum            'C38 H44 N2'
_chemical_formula_weight         528.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 100.593(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.8901(3)
_cell_length_b                   11.4265(5)
_cell_length_c                   13.5336(5)
_cell_measurement_reflns_used    10560
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      76.1440
_cell_measurement_theta_min      3.8050
_cell_volume                     1503.36(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 10.5357
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21977
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.076
_diffrn_reflns_theta_min         4.548
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.504
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_description       plate
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 2273 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     485
_refine_ls_number_reflns         5675
_refine_ls_number_restraints     433
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0552
_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)+(0.1130P)²+0.1234P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1665
_refine_ls_wR_factor_ref         0.1707
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                5267
_reflns_number_total             5675
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00734_si_003.cif
_cod_data_source_block           6b
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4038681
_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_min   0.884
_shelx_estimated_absorpt_t_max   0.966
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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
C1 C 0.9979(3) 0.5141(3) 0.4225(2) 0.0525(7) Uani 1 1 d . . . . .
C2 C 1.0639(3) 0.6160(4) 0.4538(2) 0.0568(8) Uani 1 1 d . . . . .
H2 H 1.022431 0.667896 0.494275 0.068 Uiso 1 1 calc R U . . .
C3 C 1.1910(3) 0.6473(4) 0.4288(3) 0.0632(9) Uani 1 1 d . . . . .
H3 H 1.235147 0.718224 0.453150 0.076 Uiso 1 1 calc R U . . .
C4 C 1.2505(3) 0.5733(4) 0.3683(3) 0.0655(10) Uani 1 1 d . . . . .
H4 H 1.334795 0.594814 0.348991 0.079 Uiso 1 1 calc R U . . .
C5 C 1.2498(3) 0.3872(4) 0.2763(3) 0.0654(9) Uani 1 1 d . . . . .
H5 H 1.332960 0.409042 0.255516 0.079 Uiso 1 1 calc R U . . .
C6 C 1.1934(3) 0.2810(4) 0.2493(3) 0.0660(10) Uani 1 1 d . . . . .
H6 H 1.236534 0.229209 0.209753 0.079 Uiso 1 1 calc R U . . .
C7 C 1.0698(3) 0.2481(4) 0.2803(2) 0.0599(8) Uani 1 1 d . . . . .
H7 H 1.031785 0.172840 0.263072 0.072 Uiso 1 1 calc R U . . .
C8 C 1.0046(3) 0.3224(3) 0.3345(2) 0.0532(7) Uani 1 1 d . . . . .
H8 H 0.920828 0.298932 0.353533 0.064 Uiso 1 1 calc R U . . .
C9 C 1.0605(3) 0.4351(3) 0.3632(2) 0.0513(7) Uani 1 1 d . . . . .
C10 C 1.1872(3) 0.4661(4) 0.3348(2) 0.0546(8) Uani 1 1 d . . . . .
C11 C 0.4956(3) 0.4084(3) 0.5699(2) 0.0543(8) Uani 1 1 d . . . . .
C12 C 0.4303(3) 0.3054(4) 0.5374(2) 0.0594(8) Uani 1 1 d . . . . .
H12 H 0.472729 0.254579 0.496709 0.071 Uiso 1 1 calc R U . . .
C13 C 0.3042(3) 0.2722(4) 0.5616(3) 0.0614(9) Uani 1 1 d . . . . .
H13 H 0.261748 0.200763 0.536916 0.074 Uiso 1 1 calc R U . . .
C14 C 0.2423(3) 0.3442(4) 0.6216(3) 0.0629(9) Uani 1 1 d . . . . .
H14 H 0.157410 0.321845 0.639345 0.076 Uiso 1 1 calc R U . . .
C15 C 0.2414(3) 0.5283(4) 0.7174(3) 0.0633(9) Uani 1 1 d . . . . .
H15 H 0.157587 0.505575 0.736697 0.076 Uiso 1 1 calc R U . . .
C16 C 0.2987(4) 0.6334(4) 0.7479(3) 0.0674(10) Uani 1 1 d . . . . .
H16 H 0.255121 0.683506 0.788515 0.081 Uiso 1 1 calc R U . . .
C17 C 0.4229(3) 0.6679(4) 0.7193(2) 0.0590(8) Uani 1 1 d . . . . .
H17 H 0.461432 0.742072 0.740068 0.071 Uiso 1 1 calc R U . . .
C18 C 0.4886(3) 0.5969(3) 0.6624(2) 0.0563(8) Uani 1 1 d . . . . .
H18 H 0.572543 0.621637 0.644391 0.068 Uiso 1 1 calc R U . . .
C19 C 0.4315(3) 0.4850(3) 0.6296(2) 0.0543(8) Uani 1 1 d . . . . .
C20 C 0.3051(3) 0.4525(4) 0.6572(2) 0.0552(8) Uani 1 1 d . . . . .
C21 C 0.8665(3) 0.4852(3) 0.4571(2) 0.0514(7) Uani 1 1 d . . . . .
C22 C 0.7390(3) 0.4730(3) 0.3913(2) 0.0529(8) Uani 1 1 d . . . . .
C23 C 0.6231(3) 0.4503(3) 0.4330(2) 0.0531(8) Uani 1 1 d . . . . .
H23 H 0.537017 0.441818 0.389004 0.064 Uiso 1 1 calc R U . . .
C24 C 0.6271(3) 0.4393(3) 0.5359(2) 0.0523(7) Uani 1 1 d . . . . .
C25 C 0.7545(3) 0.4509(3) 0.6015(2) 0.0524(7) Uani 1 1 d . . . . .
C26 C 0.8707(3) 0.4745(3) 0.5600(2) 0.0540(8) Uani 1 1 d . . . . .
H26 H 0.956597 0.483703 0.604008 0.065 Uiso 1 1 calc R U . . .
C27 C 0.7246(3) 0.4908(4) 0.2789(2) 0.0565(8) Uani 1 1 d . . . . .
H27A H 0.758049 0.421694 0.249338 0.068 Uiso 0.637(6) 1 d R U P A 1
H27B H 0.780499 0.556784 0.266008 0.068 Uiso 0.637(6) 1 d R U P A 1
H27C H 0.720379 0.414984 0.246118 0.068 Uiso 0.363(6) 1 d R U P A 2
H27D H 0.805039 0.531574 0.264988 0.068 Uiso 0.363(6) 1 d R U P A 2
C33 C 0.7686(3) 0.4311(4) 0.7134(2) 0.0580(9) Uani 1 1 d . . . . .
H33A H 0.697864 0.377229 0.725895 0.070 Uiso 0.363(6) 1 d R U P A 1
H33B H 0.755774 0.504559 0.746385 0.070 Uiso 0.363(6) 1 d R U P A 1
H33C H 0.690004 0.387499 0.727185 0.070 Uiso 0.637(6) 1 d R U P A 2
H33D H 0.771684 0.505639 0.748015 0.070 Uiso 0.637(6) 1 d R U P A 2
N1 N 0.5786(11) 0.5139(10) 0.2305(8) 0.063(2) Uani 0.637(6) 1 d . . P A 1
H1 H 0.512170 0.528117 0.261702 0.075 Uiso 0.637(6) 1 d R U P A 1
N2A N 0.9047(9) 0.3999(9) 0.7567(6) 0.0393(19) Uani 0.363(6) 1 d . U P A 2
H2A H 0.927534 0.346805 0.717894 0.047 Uiso 0.363(6) 1 d R U P A 2
C28 C 0.5600(7) 0.5342(9) 0.1227(6) 0.0561(18) Uani 0.637(6) 1 d . . P A 1
H28 H 0.607399 0.469270 0.093112 0.067 Uiso 0.637(6) 1 calc R U P A 1
C29 C 0.6205(6) 0.6482(8) 0.0944(5) 0.0783(18) Uani 0.637(6) 1 d . . P A 1
H29 H 0.718628 0.649861 0.129739 0.094 Uiso 0.637(6) 1 calc R U P A 1
C30 C 0.6219(7) 0.6552(10) -0.0182(5) 0.096(3) Uani 0.637(6) 1 d . . P A 1
H30A H 0.675450 0.589844 -0.037792 0.143 Uiso 0.637(6) 1 calc R U P A 1
H30B H 0.663786 0.729356 -0.033196 0.143 Uiso 0.637(6) 1 calc R U P A 1
H30C H 0.527420 0.651075 -0.055892 0.143 Uiso 0.637(6) 1 calc R U P A 1
C31 C 0.5504(19) 0.7574(12) 0.1291(10) 0.108(4) Uani 0.637(6) 1 d . . P A 1
H31A H 0.455615 0.762392 0.092130 0.162 Uiso 0.637(6) 1 calc R U P A 1
H31B H 0.601174 0.827622 0.115830 0.162 Uiso 0.637(6) 1 calc R U P A 1
H31C H 0.550029 0.751650 0.201256 0.162 Uiso 0.637(6) 1 calc R U P A 1
C32 C 0.4045(5) 0.5245(8) 0.0794(4) 0.0761(18) Uani 0.637(6) 1 d . . P A 1
H32A H 0.373096 0.444724 0.089199 0.114 Uiso 0.637(6) 1 calc R U P A 1
H32B H 0.388102 0.542707 0.007414 0.114 Uiso 0.637(6) 1 calc R U P A 1
H32C H 0.353746 0.579943 0.114088 0.114 Uiso 0.637(6) 1 calc R U P A 1
C34A C 0.9126(14) 0.3528(12) 0.8619(11) 0.056(3) Uani 0.363(6) 1 d . U P A 2
H34A H 0.822552 0.314826 0.865409 0.067 Uiso 0.363(6) 1 calc R U P A 2
C35A C 0.9381(18) 0.4461(19) 0.9414(13) 0.063(4) Uani 0.363(6) 1 d . . P A 2
H35A H 0.876186 0.513577 0.917685 0.076 Uiso 0.363(6) 1 calc R U P A 2
C36A C 0.908(2) 0.4073(19) 1.0408(14) 0.083(5) Uani 0.363(6) 1 d . . P A 2
H36A H 0.916754 0.474019 1.087040 0.124 Uiso 0.363(6) 1 calc R U P A 2
H36B H 0.972755 0.345904 1.068793 0.124 Uiso 0.363(6) 1 calc R U P A 2
H36C H 0.813680 0.376616 1.031506 0.124 Uiso 0.363(6) 1 calc R U P A 2
C37A C 1.0825(19) 0.489(2) 0.9551(17) 0.079(5) Uani 0.363(6) 1 d . . P A 2
H37A H 1.102933 0.513280 0.890059 0.119 Uiso 0.363(6) 1 calc R U P A 2
H37B H 1.145317 0.425777 0.982918 0.119 Uiso 0.363(6) 1 calc R U P A 2
H37C H 1.094274 0.555481 1.001477 0.119 Uiso 0.363(6) 1 calc R U P A 2
C38A C 1.0259(14) 0.2547(12) 0.8751(10) 0.062(3) Uani 0.363(6) 1 d . U P A 2
H38A H 1.109707 0.285560 0.855730 0.075 Uiso 0.363(6) 1 calc R U P A 2
H38B H 0.992390 0.187723 0.832382 0.093 Uiso 0.363(6) 1 calc R U P A 2
H38C H 1.046194 0.229738 0.945585 0.093 Uiso 0.363(6) 1 calc R U P A 2
N1A N 0.604(2) 0.554(2) 0.2386(16) 0.062(4) Uani 0.363(6) 1 d . . P A 2
H1A H 0.567877 0.595948 0.279764 0.075 Uiso 0.363(6) 1 d R U P A 2
N2 N 0.8980(6) 0.3611(6) 0.7522(4) 0.0499(13) Uani 0.637(6) 1 d . U P A 1
H2B H 0.890(6) 0.300(6) 0.720(5) 0.060 Uiso 0.637(6) 1 d . U P A 1
C28A C 0.5899(16) 0.5793(15) 0.1281(12) 0.058(3) Uani 0.363(6) 1 d . . P A 2
H28A H 0.680242 0.603676 0.111624 0.069 Uiso 0.363(6) 1 calc R U P A 2
C29A C 0.4802(12) 0.6710(12) 0.0922(7) 0.073(3) Uani 0.363(6) 1 d . . P A 2
H29A H 0.391258 0.645990 0.110734 0.088 Uiso 0.363(6) 1 calc R U P A 2
C30A C 0.462(2) 0.6820(14) -0.0208(9) 0.110(6) Uani 0.363(6) 1 d . . P A 2
H30D H 0.551625 0.695557 -0.039857 0.164 Uiso 0.363(6) 1 calc R U P A 2
H30E H 0.400729 0.747973 -0.043539 0.164 Uiso 0.363(6) 1 calc R U P A 2
H30F H 0.421708 0.609746 -0.052358 0.164 Uiso 0.363(6) 1 calc R U P A 2
C31A C 0.525(2) 0.786(2) 0.143(2) 0.083(5) Uani 0.363(6) 1 d . . P A 2
H31D H 0.543680 0.774858 0.215669 0.124 Uiso 0.363(6) 1 calc R U P A 2
H31E H 0.450930 0.843538 0.124586 0.124 Uiso 0.363(6) 1 calc R U P A 2
H31F H 0.607797 0.813447 0.120359 0.124 Uiso 0.363(6) 1 calc R U P A 2
C32A C 0.5418(12) 0.4595(12) 0.0757(7) 0.069(3) Uani 0.363(6) 1 d . . P A 2
H32D H 0.451981 0.437992 0.091005 0.103 Uiso 0.363(6) 1 calc R U P A 2
H32E H 0.609120 0.398512 0.100696 0.103 Uiso 0.363(6) 1 calc R U P A 2
H32F H 0.534456 0.467466 0.002820 0.103 Uiso 0.363(6) 1 calc R U P A 2
C34 C 0.9028(6) 0.3074(8) 0.8492(5) 0.0579(15) Uani 0.637(6) 1 d . . P A 1
H34 H 0.813578 0.265480 0.846967 0.069 Uiso 0.637(6) 1 calc R U P A 1
C35 C 0.9160(12) 0.3960(11) 0.9338(8) 0.076(3) Uani 0.637(6) 1 d . . P A 1
H35 H 0.843145 0.456525 0.913557 0.092 Uiso 0.637(6) 1 calc R U P A 1
C36 C 0.8905(13) 0.3404(15) 1.0328(7) 0.105(4) Uani 0.637(6) 1 d . . P A 1
H36D H 0.969871 0.292185 1.061923 0.157 Uiso 0.637(6) 1 calc R U P A 1
H36E H 0.807907 0.291329 1.019032 0.157 Uiso 0.637(6) 1 calc R U P A 1
H36F H 0.877626 0.402305 1.080315 0.157 Uiso 0.637(6) 1 calc R U P A 1
C37 C 1.052(2) 0.458(2) 0.9506(15) 0.129(6) Uani 0.637(6) 1 d . . P A 1
H37D H 1.123596 0.405541 0.985865 0.193 Uiso 0.637(6) 1 calc R U P A 1
H37E H 1.046979 0.528080 0.991381 0.193 Uiso 0.637(6) 1 calc R U P A 1
H37F H 1.074719 0.480393 0.885724 0.193 Uiso 0.637(6) 1 calc R U P A 1
C38 C 1.0148(10) 0.2153(9) 0.8602(7) 0.077(2) Uani 0.637(6) 1 d . U P A 1
H38D H 1.031383 0.184722 0.929002 0.116 Uiso 0.637(6) 1 calc R U P A 1
H38E H 1.099563 0.250377 0.845905 0.116 Uiso 0.637(6) 1 calc R U P A 1
H38F H 0.985819 0.151359 0.812799 0.116 Uiso 0.637(6) 1 calc R U P A 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
C2 C1 C9 119.0(3) . . ?
C2 C1 C21 119.0(3) . . ?
C9 C1 C21 121.9(3) . . ?
C1 C2 C3 122.7(3) . . ?
C1 C2 H2 118.6 . . ?
C3 C2 H2 118.6 . . ?
C4 C3 C2 118.9(4) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C10 120.5(3) . . ?
C3 C4 H4 119.7 . . ?
C10 C4 H4 119.7 . . ?
C6 C5 C10 121.3(3) . . ?
C6 C5 H5 119.3 . . ?
C10 C5 H5 119.3 . . ?
C5 C6 C7 119.5(4) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 121.0(4) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 120.8(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C1 119.3(3) . . ?
C10 C9 C8 117.9(3) . . ?
C1 C9 C8 122.7(3) . . ?
C4 C10 C5 121.2(3) . . ?
C4 C10 C9 119.4(3) . . ?
C5 C10 C9 119.3(4) . . ?
C12 C11 C19 118.6(3) . . ?
C12 C11 C24 119.1(3) . . ?
C19 C11 C24 122.3(3) . . ?
C11 C12 C13 122.9(4) . . ?
C11 C12 H12 118.5 . . ?
C13 C12 H12 118.5 . . ?
C14 C13 C12 119.2(4) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C20 120.3(3) . . ?
C13 C14 H14 119.9 . . ?
C20 C14 H14 119.9 . . ?
C16 C15 C20 120.7(3) . . ?
C16 C15 H15 119.6 . . ?
C20 C15 H15 119.6 . . ?
C15 C16 C17 120.0(4) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 121.2(4) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 120.3(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C11 C19 C20 119.8(4) . . ?
C11 C19 C18 122.3(3) . . ?
C20 C19 C18 117.9(3) . . ?
C15 C20 C19 119.9(4) . . ?
C15 C20 C14 120.8(3) . . ?
C19 C20 C14 119.2(3) . . ?
C26 C21 C22 118.8(3) . . ?
C26 C21 C1 117.7(2) . . ?
C22 C21 C1 123.4(3) . . ?
C23 C22 C21 118.0(3) . . ?
C23 C22 C27 120.0(3) . . ?
C21 C22 C27 122.0(3) . . ?
C24 C23 C22 123.3(3) . . ?
C24 C23 H23 118.4 . . ?
C22 C23 H23 118.4 . . ?
C23 C24 C25 118.7(3) . . ?
C23 C24 C11 117.5(3) . . ?
C25 C24 C11 123.6(3) . . ?
C26 C25 C24 118.1(3) . . ?
C26 C25 C33 120.1(3) . . ?
C24 C25 C33 121.7(3) . . ?
C21 C26 C25 123.1(3) . . ?
C21 C26 H26 118.5 . . ?
C25 C26 H26 118.5 . . ?
N1A C27 C22 111.8(9) . . ?
N1 C27 C22 111.6(5) . . ?
N1 C27 H27A 109.8 . . ?
C22 C27 H27A 109.2 . . ?
N1 C27 H27B 108.7 . . ?
C22 C27 H27B 109.4 . . ?
H27A C27 H27B 108.1 . . ?
N1A C27 H27C 108.6 . . ?
C22 C27 H27C 109.1 . . ?
N1A C27 H27D 110.0 . . ?
C22 C27 H27D 109.2 . . ?
H27C C27 H27D 108.0 . . ?
N2A C33 C25 111.1(4) . . ?
C25 C33 N2 110.0(3) . . ?
C25 C33 H33A 109.4 . . ?
N2 C33 H33A 101.2 . . ?
C25 C33 H33B 109.6 . . ?
N2 C33 H33B 118.0 . . ?
H33A C33 H33B 108.0 . . ?
N2A C33 H33C 121.9 . . ?
C25 C33 H33C 109.9 . . ?
N2A C33 H33D 94.5 . . ?
C25 C33 H33D 109.9 . . ?
H33C C33 H33D 108.2 . . ?
C28 N1 C27 113.7(8) . . ?
C28 N1 H1 119.7 . . ?
C27 N1 H1 125.6 . . ?
C33 N2A C34A 111.2(8) . . ?
C33 N2A H2A 105.2 . . ?
C34A N2A H2A 110.5 . . ?
N1 C28 C29 114.1(7) . . ?
N1 C28 C32 107.6(7) . . ?
C29 C28 C32 112.2(6) . . ?
N1 C28 H28 107.5 . . ?
C29 C28 H28 107.5 . . ?
C32 C28 H28 107.5 . . ?
C28 C29 C30 112.0(7) . . ?
C28 C29 C31 113.5(8) . . ?
C30 C29 C31 110.3(8) . . ?
C28 C29 H29 106.8 . . ?
C30 C29 H29 106.8 . . ?
C31 C29 H29 106.8 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C28 C32 H32A 109.5 . . ?
C28 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C28 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C35A C34A N2A 113.3(13) . . ?
C35A C34A C38A 113.7(13) . . ?
N2A C34A C38A 105.9(10) . . ?
C35A C34A H34A 107.9 . . ?
N2A C34A H34A 107.9 . . ?
C38A C34A H34A 107.9 . . ?
C37A C35A C36A 109.4(15) . . ?
C37A C35A C34A 110.6(14) . . ?
C36A C35A C34A 113.5(17) . . ?
C37A C35A H35A 107.7 . . ?
C36A C35A H35A 107.7 . . ?
C34A C35A H35A 107.7 . . ?
C35A C36A H36A 109.5 . . ?
C35A C36A H36B 109.5 . . ?
H36A C36A H36B 109.5 . . ?
C35A C36A H36C 109.5 . . ?
H36A C36A H36C 109.5 . . ?
H36B C36A H36C 109.5 . . ?
C35A C37A H37A 109.5 . . ?
C35A C37A H37B 109.5 . . ?
H37A C37A H37B 109.5 . . ?
C35A C37A H37C 109.5 . . ?
H37A C37A H37C 109.5 . . ?
H37B C37A H37C 109.5 . . ?
C34A C38A H38A 109.5 . . ?
C34A C38A H38B 109.5 . . ?
H38A C38A H38B 109.5 . . ?
C34A C38A H38C 109.5 . . ?
H38A C38A H38C 109.5 . . ?
H38B C38A H38C 109.5 . . ?
C27 N1A C28A 113.5(17) . . ?
C27 N1A H1A 117.2 . . ?
C28A N1A H1A 124.3 . . ?
C34 N2 C33 115.1(5) . . ?
C34 N2 H2B 96(4) . . ?
C33 N2 H2B 106(4) . . ?
N1A C28A C29A 112.3(15) . . ?
N1A C28A C32A 104.4(12) . . ?
C29A C28A C32A 108.4(11) . . ?
N1A C28A H28A 110.5 . . ?
C29A C28A H28A 110.5 . . ?
C32A C28A H28A 110.5 . . ?
C31A C29A C30A 110.9(16) . . ?
C31A C29A C28A 108.9(12) . . ?
C30A C29A C28A 109.0(11) . . ?
C31A C29A H29A 109.3 . . ?
C30A C29A H29A 109.3 . . ?
C28A C29A H29A 109.3 . . ?
C29A C30A H30D 109.5 . . ?
C29A C30A H30E 109.5 . . ?
H30D C30A H30E 109.5 . . ?
C29A C30A H30F 109.5 . . ?
H30D C30A H30F 109.5 . . ?
H30E C30A H30F 109.5 . . ?
C29A C31A H31D 109.5 . . ?
C29A C31A H31E 109.5 . . ?
H31D C31A H31E 109.5 . . ?
C29A C31A H31F 109.5 . . ?
H31D C31A H31F 109.5 . . ?
H31E C31A H31F 109.5 . . ?
C28A C32A H32D 109.5 . . ?
C28A C32A H32E 109.5 . . ?
H32D C32A H32E 109.5 . . ?
C28A C32A H32F 109.5 . . ?
H32D C32A H32F 109.5 . . ?
H32E C32A H32F 109.5 . . ?
N2 C34 C38 106.6(6) . . ?
N2 C34 C35 112.8(8) . . ?
C38 C34 C35 115.4(6) . . ?
N2 C34 H34 107.2 . . ?
C38 C34 H34 107.2 . . ?
C35 C34 H34 107.2 . . ?
C37 C35 C34 112.3(10) . . ?
C37 C35 C36 110.3(12) . . ?
C34 C35 C36 112.0(10) . . ?
C37 C35 H35 107.3 . . ?
C34 C35 H35 107.3 . . ?
C36 C35 H35 107.3 . . ?
C35 C36 H36D 109.5 . . ?
C35 C36 H36E 109.5 . . ?
H36D C36 H36E 109.5 . . ?
C35 C36 H36F 109.5 . . ?
H36D C36 H36F 109.5 . . ?
H36E C36 H36F 109.5 . . ?
C35 C37 H37D 109.5 . . ?
C35 C37 H37E 109.5 . . ?
H37D C37 H37E 109.5 . . ?
C35 C37 H37F 109.5 . . ?
H37D C37 H37F 109.5 . . ?
H37E C37 H37F 109.5 . . ?
C34 C38 H38D 109.5 . . ?
C34 C38 H38E 109.5 . . ?
H38D C38 H38E 109.5 . . ?
C34 C38 H38F 109.5 . . ?
H38D C38 H38F 109.5 . . ?
H38E C38 H38F 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
C1 C2 1.364(5) . ?
C1 C9 1.422(5) . ?
C1 C21 1.497(4) . ?
C2 C3 1.406(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(6) . ?
C3 H3 0.9500 . ?
C4 C10 1.412(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.358(7) . ?
C5 C10 1.416(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.415(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.359(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.427(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.422(4) . ?
C11 C12 1.375(5) . ?
C11 C19 1.416(5) . ?
C11 C24 1.500(4) . ?
C12 C13 1.399(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.376(6) . ?
C13 H13 0.9500 . ?
C14 C20 1.428(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.359(6) . ?
C15 C20 1.415(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.411(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.363(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.435(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.418(4) . ?
C21 C26 1.391(4) . ?
C21 C22 1.411(4) . ?
C22 C23 1.392(4) . ?
C22 C27 1.515(4) . ?
C23 C24 1.391(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.408(4) . ?
C25 C26 1.395(4) . ?
C25 C33 1.512(4) . ?
C26 H26 0.9500 . ?
C27 N1A 1.41(2) . ?
C27 N1 1.495(11) . ?
C27 H27A 0.9698 . ?
C27 H27B 0.9699 . ?
C27 H27C 0.9700 . ?
C27 H27D 0.9700 . ?
C33 N2A 1.411(9) . ?
C33 N2 1.519(7) . ?
C33 H33A 0.9698 . ?
C33 H33B 0.9703 . ?
C33 H33C 0.9699 . ?
C33 H33D 0.9701 . ?
N1 C28 1.454(14) . ?
N1 H1 0.8601 . ?
N2A C34A 1.510(18) . ?
N2A H2A 0.8598 . ?
C28 C29 1.511(11) . ?
C28 C32 1.546(8) . ?
C28 H28 1.0000 . ?
C29 C30 1.529(8) . ?
C29 C31 1.542(17) . ?
C29 H29 1.0000 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C34A C35A 1.50(2) . ?
C34A C38A 1.572(18) . ?
C34A H34A 1.0000 . ?
C35A C37A 1.49(2) . ?
C35A C36A 1.50(2) . ?
C35A H35A 1.0000 . ?
C36A H36A 0.9800 . ?
C36A H36B 0.9800 . ?
C36A H36C 0.9800 . ?
C37A H37A 0.9800 . ?
C37A H37B 0.9800 . ?
C37A H37C 0.9800 . ?
C38A H38A 0.9800 . ?
C38A H38B 0.9800 . ?
C38A H38C 0.9800 . ?
N1A C28A 1.50(3) . ?
N1A H1A 0.8600 . ?
N2 C34 1.441(8) . ?
N2 H2B 0.82(7) . ?
C28A C29A 1.52(2) . ?
C28A C32A 1.574(18) . ?
C28A H28A 1.0000 . ?
C29A C31A 1.51(3) . ?
C29A C30A 1.512(16) . ?
C29A H29A 1.0000 . ?
C30A H30D 0.9800 . ?
C30A H30E 0.9800 . ?
C30A H30F 0.9800 . ?
C31A H31D 0.9800 . ?
C31A H31E 0.9800 . ?
C31A H31F 0.9800 . ?
C32A H32D 0.9800 . ?
C32A H32E 0.9800 . ?
C32A H32F 0.9800 . ?
C34 C38 1.515(11) . ?
C34 C35 1.516(13) . ?
C34 H34 1.0000 . ?
C35 C37 1.500(15) . ?
C35 C36 1.546(15) . ?
C35 H35 1.0000 . ?
C36 H36D 0.9800 . ?
C36 H36E 0.9800 . ?
C36 H36F 0.9800 . ?
C37 H37D 0.9800 . ?
C37 H37E 0.9800 . ?
C37 H37F 0.9800 . ?
C38 H38D 0.9800 . ?
C38 H38E 0.9800 . ?
C38 H38F 0.9800 . ?
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
C9 C1 C2 C3 1.0(5) . . . . ?
C21 C1 C2 C3 176.9(3) . . . . ?
C1 C2 C3 C4 1.3(5) . . . . ?
C2 C3 C4 C10 -2.1(5) . . . . ?
C10 C5 C6 C7 -0.2(5) . . . . ?
C5 C6 C7 C8 1.8(5) . . . . ?
C6 C7 C8 C9 -1.2(5) . . . . ?
C2 C1 C9 C10 -2.5(4) . . . . ?
C21 C1 C9 C10 -178.3(3) . . . . ?
C2 C1 C9 C8 174.4(3) . . . . ?
C21 C1 C9 C8 -1.4(4) . . . . ?
C7 C8 C9 C10 -1.1(4) . . . . ?
C7 C8 C9 C1 -178.0(3) . . . . ?
C3 C4 C10 C5 -177.3(3) . . . . ?
C3 C4 C10 C9 0.6(5) . . . . ?
C6 C5 C10 C4 175.9(3) . . . . ?
C6 C5 C10 C9 -2.0(5) . . . . ?
C1 C9 C10 C4 1.7(4) . . . . ?
C8 C9 C10 C4 -175.3(3) . . . . ?
C1 C9 C10 C5 179.7(3) . . . . ?
C8 C9 C10 C5 2.6(4) . . . . ?
C19 C11 C12 C13 -0.8(5) . . . . ?
C24 C11 C12 C13 -177.0(3) . . . . ?
C11 C12 C13 C14 -0.8(5) . . . . ?
C12 C13 C14 C20 1.1(5) . . . . ?
C20 C15 C16 C17 0.2(5) . . . . ?
C15 C16 C17 C18 -1.0(5) . . . . ?
C16 C17 C18 C19 0.5(5) . . . . ?
C12 C11 C19 C20 2.2(4) . . . . ?
C24 C11 C19 C20 178.2(3) . . . . ?
C12 C11 C19 C18 -176.7(3) . . . . ?
C24 C11 C19 C18 -0.6(4) . . . . ?
C17 C18 C19 C11 179.7(3) . . . . ?
C17 C18 C19 C20 0.8(4) . . . . ?
C16 C15 C20 C19 1.1(5) . . . . ?
C16 C15 C20 C14 -177.4(3) . . . . ?
C11 C19 C20 C15 179.5(3) . . . . ?
C18 C19 C20 C15 -1.6(4) . . . . ?
C11 C19 C20 C14 -1.9(4) . . . . ?
C18 C19 C20 C14 177.0(3) . . . . ?
C13 C14 C20 C15 178.9(3) . . . . ?
C13 C14 C20 C19 0.3(5) . . . . ?
C2 C1 C21 C26 -60.0(4) . . . . ?
C9 C1 C21 C26 115.8(4) . . . . ?
C2 C1 C21 C22 117.3(4) . . . . ?
C9 C1 C21 C22 -66.9(5) . . . . ?
C26 C21 C22 C23 -0.3(5) . . . . ?
C1 C21 C22 C23 -177.6(3) . . . . ?
C26 C21 C22 C27 176.2(4) . . . . ?
C1 C21 C22 C27 -1.1(6) . . . . ?
C21 C22 C23 C24 0.2(6) . . . . ?
C27 C22 C23 C24 -176.4(4) . . . . ?
C22 C23 C24 C25 -0.5(6) . . . . ?
C22 C23 C24 C11 -176.8(4) . . . . ?
C12 C11 C24 C23 59.5(5) . . . . ?
C19 C11 C24 C23 -116.5(4) . . . . ?
C12 C11 C24 C25 -116.6(4) . . . . ?
C19 C11 C24 C25 67.3(5) . . . . ?
C23 C24 C25 C26 0.9(5) . . . . ?
C11 C24 C25 C26 177.0(4) . . . . ?
C23 C24 C25 C33 -175.3(4) . . . . ?
C11 C24 C25 C33 0.8(6) . . . . ?
C22 C21 C26 C25 0.8(6) . . . . ?
C1 C21 C26 C25 178.2(4) . . . . ?
C24 C25 C26 C21 -1.0(6) . . . . ?
C33 C25 C26 C21 175.2(4) . . . . ?
C23 C22 C27 N1A 38.3(9) . . . . ?
C21 C22 C27 N1A -138.2(8) . . . . ?
C23 C22 C27 N1 16.0(7) . . . . ?
C21 C22 C27 N1 -160.5(5) . . . . ?
C26 C25 C33 N2A -20.3(7) . . . . ?
C24 C25 C33 N2A 155.7(6) . . . . ?
C26 C25 C33 N2 -38.7(6) . . . . ?
C24 C25 C33 N2 137.4(4) . . . . ?
C22 C27 N1 C28 178.6(7) . . . . ?
C25 C33 N2A C34A -166.7(7) . . . . ?
C27 N1 C28 C29 -69.2(10) . . . . ?
C27 N1 C28 C32 165.5(7) . . . . ?
N1 C28 C29 C30 169.5(7) . . . . ?
C32 C28 C29 C30 -67.7(8) . . . . ?
N1 C28 C29 C31 -64.7(10) . . . . ?
C32 C28 C29 C31 58.1(9) . . . . ?
C33 N2A C34A C35A -89.8(13) . . . . ?
C33 N2A C34A C38A 144.9(9) . . . . ?
N2A C34A C35A C37A -72.7(19) . . . . ?
C38A C34A C35A C37A 48(2) . . . . ?
N2A C34A C35A C36A 164.0(14) . . . . ?
C38A C34A C35A C36A -75.0(18) . . . . ?
C22 C27 N1A C28A 176.9(10) . . . . ?
C25 C33 N2 C34 -162.6(5) . . . . ?
C27 N1A C28A C29A -166.3(12) . . . . ?
C27 N1A C28A C32A 76.4(14) . . . . ?
N1A C28A C29A C31A 64.6(18) . . . . ?
C32A C28A C29A C31A 179.5(14) . . . . ?
N1A C28A C29A C30A -174.2(13) . . . . ?
C32A C28A C29A C30A -59.4(15) . . . . ?
C33 N2 C34 C38 163.7(6) . . . . ?
C33 N2 C34 C35 -68.6(8) . . . . ?
N2 C34 C35 C37 -67.2(14) . . . . ?
C38 C34 C35 C37 55.7(15) . . . . ?
N2 C34 C35 C36 168.0(8) . . . . ?
C38 C34 C35 C36 -69.0(11) . . . . ?
