#------------------------------------------------------------------------------
#$Date: 2025-09-24 01:47:49 +0300 (Wed, 24 Sep 2025) $
#$Revision: 302230 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/58/1575862.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_1575862
loop_
_publ_author_name
'He, Jun'
'Yang, Zun'
'Lin, Lili'
'Feng, Xiaoming'
_publ_section_title
;
 Enantioselective synthesis of C-C and C-N axially chiral pyrazole-based
 heterobiaryls
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC06841J
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C32 H26 N4 O3)'
_chemical_formula_sum            'C64 H52 N8 O6'
_chemical_formula_weight         1029.13
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2025-06-27 deposited with the CCDC.	2025-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                93.9470(10)
_cell_angle_beta                 96.9580(10)
_cell_angle_gamma                96.7230(10)
_cell_formula_units_Z            1
_cell_length_a                   9.4969(2)
_cell_length_b                   11.5694(3)
_cell_length_c                   12.2031(3)
_cell_measurement_reflns_used    9098
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      80.13
_cell_measurement_theta_min      3.66
_cell_volume                     1317.08(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            44167
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.783
_diffrn_reflns_theta_min         3.662
_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.8424
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, Hexane'
_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
; 
 Flack x determined using 4864 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.09(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     715
_refine_ls_number_reflns         10814
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0281
_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)+(0.0336P)²+0.1675P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0717
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_full    0.953
_reflns_Friedel_fraction_max     0.887
_reflns_number_gt                10546
_reflns_number_total             10814
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc06841j2.cif
_cod_data_source_block           hqw027
_cod_original_cell_volume        1317.07(5)
_cod_database_code               1575862
_shelx_shelxl_version_number     2019/1
_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   0.849
_shelx_estimated_absorpt_t_max   0.956
loop_
_space_group_symop_operation_xyz
'x, y, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.04452(14) 0.32572(13) 0.49868(10) 0.0354(3) Uani 1 1 d . . . . .
O2X O 0.2531(8) 0.339(4) 0.4329(7) 0.080(6) Uani 0.59(7) 1 d D . P A 1
O2Y O 0.2390(16) 0.2888(16) 0.4228(12) 0.041(4) Uani 0.41(7) 1 d D . P A 2
O3A O 0.47194(15) 0.14352(16) 0.20538(14) 0.0503(4) Uani 1 1 d . . . . .
N1A N 0.08926(15) 0.33272(13) 0.20784(11) 0.0277(3) Uani 1 1 d . . . . .
N2A N 0.29678(17) 0.21240(14) 0.03161(12) 0.0309(3) Uani 1 1 d . . . . .
N3A N 0.33309(15) 0.32847(13) 0.02288(12) 0.0272(3) Uani 1 1 d . . . . .
N4A N 0.14083(16) 0.02590(14) 0.27885(13) 0.0325(3) Uani 1 1 d . . . . .
C1A C 0.0074(3) 0.3090(2) 0.68621(17) 0.0500(5) Uani 1 1 d . . . . .
H1AA H 0.052872 0.297226 0.760367 0.075 Uiso 1 1 calc R U . . .
H1AB H -0.070626 0.245787 0.662270 0.075 Uiso 1 1 calc R U . . .
H1AC H -0.031014 0.384064 0.688091 0.075 Uiso 1 1 calc R U . . .
C2A C 0.1154(3) 0.3090(3) 0.60675(17) 0.0544(6) Uani 1 1 d . . . . .
H2AA H 0.194599 0.372789 0.630069 0.065 Uiso 1 1 calc R U . . .
H2AB H 0.155674 0.233852 0.604838 0.065 Uiso 1 1 calc R U . . .
C3A C 0.1234(2) 0.3249(2) 0.41593(15) 0.0375(4) Uani 1 1 d D . . . .
C4A C 0.03627(18) 0.33475(15) 0.30965(14) 0.0274(3) Uani 1 1 d . . . . .
C5A C -0.10782(19) 0.34200(16) 0.29335(14) 0.0288(3) Uani 1 1 d . . . . .
H5AA H -0.168881 0.346183 0.349282 0.035 Uiso 1 1 calc R U . . .
C6A C -0.14895(18) 0.34213(15) 0.17754(14) 0.0275(3) Uani 1 1 d . . . . .
C7A C -0.02464(18) 0.33487(15) 0.12609(14) 0.0262(3) Uani 1 1 d . . . . .
C8A C -0.0292(2) 0.33096(18) 0.01035(15) 0.0324(4) Uani 1 1 d . . . . .
H8AA H 0.054278 0.325219 -0.024328 0.039 Uiso 1 1 calc R U . . .
C9A C -0.1604(2) 0.33580(19) -0.05092(16) 0.0366(4) Uani 1 1 d . . . . .
H9AA H -0.166662 0.333833 -0.129329 0.044 Uiso 1 1 calc R U . . .
C10A C -0.2849(2) 0.34356(19) -0.00059(17) 0.0381(4) Uani 1 1 d . . . . .
H10A H -0.373173 0.346634 -0.045475 0.046 Uiso 1 1 calc R U . . .
C11A C -0.28087(19) 0.34676(17) 0.11246(16) 0.0336(4) Uani 1 1 d . . . . .
H11A H -0.365310 0.351984 0.146072 0.040 Uiso 1 1 calc R U . . .
C21A C 0.24053(18) 0.18794(15) 0.13482(13) 0.0274(3) Uani 1 1 d . . . . .
H21A H 0.143574 0.141428 0.120415 0.033 Uiso 1 1 calc R U . . .
C22A C 0.23382(17) 0.31184(16) 0.18959(14) 0.0276(3) Uani 1 1 d . . . . .
H22A H 0.296739 0.322772 0.262366 0.033 Uiso 1 1 calc R U . . .
C23A C 0.30226(17) 0.38836(16) 0.10844(14) 0.0268(3) Uani 1 1 d . . . . .
C24A C 0.33515(18) 0.51531(16) 0.12356(15) 0.0310(4) Uani 1 1 d . . . . .
C25A C 0.4133(2) 0.57576(17) 0.05112(16) 0.0342(4) Uani 1 1 d . . . . .
H25A H 0.450166 0.533503 -0.006180 0.041 Uiso 1 1 calc R U . . .
C26A C 0.4379(2) 0.69637(19) 0.06162(19) 0.0422(5) Uani 1 1 d . . . . .
H26A H 0.490449 0.736317 0.011102 0.051 Uiso 1 1 calc R U . . .
C27A C 0.3864(2) 0.7592(2) 0.1452(2) 0.0531(6) Uani 1 1 d . . . . .
H27A H 0.401724 0.842118 0.151463 0.064 Uiso 1 1 calc R U . . .
C28A C 0.3134(3) 0.7009(3) 0.2187(3) 0.0705(9) Uani 1 1 d . . . . .
H28A H 0.279542 0.743846 0.277128 0.085 Uiso 1 1 calc R U . . .
C29A C 0.2878(3) 0.5797(2) 0.2091(2) 0.0563(6) Uani 1 1 d . . . . .
H29A H 0.237627 0.540599 0.261384 0.068 Uiso 1 1 calc R U . . .
C31A C 0.34451(19) 0.12711(17) 0.20981(15) 0.0304(3) Uani 1 1 d . . . . .
C32A C 0.28371(18) 0.05297(15) 0.29290(13) 0.0266(3) Uani 1 1 d . . . . .
C33A C 0.37404(19) 0.01633(16) 0.37804(14) 0.0292(3) Uani 1 1 d . . . . .
H33A H 0.474633 0.036924 0.383745 0.035 Uiso 1 1 calc R U . . .
C34A C 0.3146(2) -0.05097(17) 0.45467(15) 0.0338(4) Uani 1 1 d . . . . .
H34A H 0.373122 -0.077421 0.514190 0.041 Uiso 1 1 calc R U . . .
C35A C 0.1680(2) -0.07825(18) 0.44170(17) 0.0375(4) Uani 1 1 d . . . . .
H35A H 0.123391 -0.123239 0.493186 0.045 Uiso 1 1 calc R U . . .
C36A C 0.0860(2) -0.03958(18) 0.35303(18) 0.0379(4) Uani 1 1 d . . . . .
H36A H -0.014642 -0.060833 0.344601 0.045 Uiso 1 1 calc R U . . .
C41A C 0.28779(19) 0.12975(16) -0.05844(14) 0.0288(3) Uani 1 1 d . . . . .
C42A C 0.2552(2) 0.01179(18) -0.04347(16) 0.0375(4) Uani 1 1 d . . . . .
H42A H 0.242303 -0.011551 0.028159 0.045 Uiso 1 1 calc R U . . .
C43A C 0.2413(3) -0.0716(2) -0.13234(19) 0.0453(5) Uani 1 1 d . . . . .
H43A H 0.217744 -0.151706 -0.121388 0.054 Uiso 1 1 calc R U . . .
C44A C 0.2615(3) -0.0395(2) -0.23666(18) 0.0469(5) Uani 1 1 d . . . . .
H44A H 0.251235 -0.096769 -0.297670 0.056 Uiso 1 1 calc R U . . .
C45A C 0.2970(2) 0.0776(2) -0.25116(17) 0.0427(5) Uani 1 1 d . . . . .
H45A H 0.313133 0.100020 -0.322499 0.051 Uiso 1 1 calc R U . . .
C46A C 0.3095(2) 0.16251(18) -0.16371(15) 0.0347(4) Uani 1 1 d . . . . .
H46A H 0.332713 0.242508 -0.175232 0.042 Uiso 1 1 calc R U . . .
O1B O 0.91236(14) 0.65217(13) 1.05513(10) 0.0360(3) Uani 1 1 d . . . . .
O2B O 0.71239(14) 0.63234(14) 0.93308(11) 0.0388(3) Uani 1 1 d . . . . .
O3B O 0.56916(17) 0.90003(16) 0.67443(12) 0.0482(4) Uani 1 1 d . . . . .
N1B N 0.90036(15) 0.64681(13) 0.75725(11) 0.0269(3) Uani 1 1 d . . . . .
N2B N 0.74704(19) 0.79153(14) 0.55265(12) 0.0339(3) Uani 1 1 d . . . . .
N3B N 0.68683(16) 0.67897(13) 0.51957(12) 0.0295(3) Uani 1 1 d . . . . .
N4B N 0.85258(18) 0.90150(16) 0.88875(13) 0.0374(4) Uani 1 1 d . . . . .
C1B C 0.9205(3) 0.6554(2) 1.25127(17) 0.0479(5) Uani 1 1 d . . . . .
H1BA H 0.864442 0.659020 1.313492 0.072 Uiso 1 1 calc R U . . .
H1BB H 0.995604 0.722362 1.260136 0.072 Uiso 1 1 calc R U . . .
H1BC H 0.964240 0.582823 1.249713 0.072 Uiso 1 1 calc R U . . .
C2B C 0.8238(2) 0.6587(2) 1.14423(15) 0.0397(4) Uani 1 1 d . . . . .
H2BA H 0.746809 0.591924 1.134534 0.048 Uiso 1 1 calc R U . . .
H2BB H 0.779448 0.732026 1.144427 0.048 Uiso 1 1 calc R U . . .
C3B C 0.84135(19) 0.63961(16) 0.95259(14) 0.0294(3) Uani 1 1 d . . . . .
C4B C 0.94105(18) 0.63540(15) 0.86935(14) 0.0279(3) Uani 1 1 d . . . . .
C5B C 1.08141(19) 0.61796(17) 0.88647(16) 0.0328(4) Uani 1 1 d . . . . .
H5BA H 1.134170 0.606486 0.955264 0.039 Uiso 1 1 calc R U . . .
C6B C 1.1343(2) 0.62015(17) 0.78199(16) 0.0336(4) Uani 1 1 d . . . . .
C7B C 1.01955(19) 0.63919(15) 0.70312(15) 0.0294(3) Uani 1 1 d . . . . .
C8B C 1.0363(2) 0.64848(18) 0.59125(17) 0.0371(4) Uani 1 1 d . . . . .
H8BA H 0.959069 0.661917 0.538522 0.045 Uiso 1 1 calc R U . . .
C9B C 1.1693(3) 0.6373(2) 0.56121(19) 0.0475(5) Uani 1 1 d . . . . .
H9BA H 1.183447 0.642287 0.485849 0.057 Uiso 1 1 calc R U . . .
C10B C 1.2852(3) 0.6186(3) 0.6386(2) 0.0555(6) Uani 1 1 d . . . . .
H10B H 1.375791 0.612180 0.614770 0.067 Uiso 1 1 calc R U . . .
C11B C 1.2690(2) 0.6097(2) 0.7479(2) 0.0480(5) Uani 1 1 d . . . . .
H11B H 1.347353 0.596708 0.799780 0.058 Uiso 1 1 calc R U . . .
C21B C 0.78533(19) 0.81218(15) 0.67196(13) 0.0280(3) Uani 1 1 d . . . . .
H21B H 0.886320 0.850091 0.691155 0.034 Uiso 1 1 calc R U . . .
C22B C 0.76756(17) 0.68632(15) 0.71036(13) 0.0260(3) Uani 1 1 d . . . . .
H22B H 0.698593 0.682060 0.766150 0.031 Uiso 1 1 calc R U . . .
C23B C 0.69784(18) 0.61686(15) 0.60322(13) 0.0272(3) Uani 1 1 d . . . . .
C24B C 0.65112(18) 0.49104(16) 0.59400(14) 0.0282(3) Uani 1 1 d . . . . .
C25B C 0.6361(2) 0.43228(17) 0.68910(15) 0.0334(4) Uani 1 1 d . . . . .
H25B H 0.654563 0.474210 0.760117 0.040 Uiso 1 1 calc R U . . .
C26B C 0.5940(2) 0.31219(19) 0.67958(17) 0.0390(4) Uani 1 1 d . . . . .
H26B H 0.583102 0.272544 0.744264 0.047 Uiso 1 1 calc R U . . .
C27B C 0.5679(2) 0.25039(18) 0.57679(19) 0.0413(4) Uani 1 1 d . . . . .
H27B H 0.540810 0.168296 0.570859 0.050 Uiso 1 1 calc R U . . .
C28B C 0.5814(2) 0.30833(18) 0.48249(17) 0.0390(4) Uani 1 1 d . . . . .
H28B H 0.562522 0.265829 0.411754 0.047 Uiso 1 1 calc R U . . .
C29B C 0.6222(2) 0.42762(17) 0.49030(15) 0.0329(4) Uani 1 1 d . . . . .
H29B H 0.630623 0.466663 0.424971 0.039 Uiso 1 1 calc R U . . .
C31B C 0.6817(2) 0.88432(16) 0.72459(14) 0.0313(4) Uani 1 1 d . . . . .
C32B C 0.7281(2) 0.93103(16) 0.84275(15) 0.0308(4) Uani 1 1 d . . . . .
C33B C 0.6446(3) 0.99950(19) 0.89838(17) 0.0415(4) Uani 1 1 d . . . . .
H33B H 0.555800 1.017175 0.863104 0.050 Uiso 1 1 calc R U . . .
C34B C 0.6945(3) 1.0415(2) 1.00725(18) 0.0483(5) Uani 1 1 d . . . . .
H34B H 0.640507 1.088944 1.048097 0.058 Uiso 1 1 calc R U . . .
C35B C 0.8235(3) 1.0132(2) 1.05484(16) 0.0449(5) Uani 1 1 d . . . . .
H35B H 0.861175 1.042463 1.128508 0.054 Uiso 1 1 calc R U . . .
C36B C 0.8974(2) 0.9416(2) 0.99371(17) 0.0437(5) Uani 1 1 d . . . . .
H36B H 0.984390 0.919836 1.028276 0.052 Uiso 1 1 calc R U . . .
C41B C 0.74442(19) 0.87795(16) 0.47909(14) 0.0286(3) Uani 1 1 d . . . . .
C42B C 0.68745(18) 0.85164(16) 0.36817(14) 0.0289(3) Uani 1 1 d . . . . .
H42B H 0.647206 0.774169 0.341940 0.035 Uiso 1 1 calc R U . . .
C43B C 0.69009(19) 0.93958(17) 0.29653(15) 0.0323(4) Uani 1 1 d . . . . .
H43B H 0.652079 0.921315 0.220840 0.039 Uiso 1 1 calc R U . . .
C44B C 0.7468(2) 1.05333(17) 0.33274(15) 0.0328(4) Uani 1 1 d . . . . .
H44B H 0.747441 1.112717 0.282714 0.039 Uiso 1 1 calc R U . . .
C45B C 0.8025(2) 1.07918(17) 0.44267(16) 0.0353(4) Uani 1 1 d . . . . .
H45B H 0.841213 1.157134 0.468393 0.042 Uiso 1 1 calc R U . . .
C46B C 0.8027(2) 0.99280(17) 0.51610(15) 0.0345(4) Uani 1 1 d . . . . .
H46B H 0.842307 1.011556 0.591388 0.041 Uiso 1 1 calc R U . . .
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3A O1A C2A 116.58(16) . . ?
C7A N1A C4A 107.75(13) . . ?
C7A N1A C22A 125.80(14) . . ?
C4A N1A C22A 125.69(14) . . ?
N3A N2A C41A 121.98(14) . . ?
N3A N2A C21A 113.16(13) . . ?
C41A N2A C21A 123.66(15) . . ?
C23A N3A N2A 109.80(14) . . ?
C36A N4A C32A 116.41(15) . . ?
O1A C2A C1A 107.89(19) . . ?
O2X C3A O1A 121.5(4) . . ?
O2Y C3A O1A 123.0(5) . . ?
O2X C3A C4A 125.7(6) . . ?
O2Y C3A C4A 123.1(7) . . ?
O1A C3A C4A 111.02(16) . . ?
C5A C4A N1A 109.49(15) . . ?
C5A C4A C3A 126.53(15) . . ?
N1A C4A C3A 123.92(15) . . ?
C4A C5A C6A 107.46(15) . . ?
C11A C6A C7A 119.84(16) . . ?
C11A C6A C5A 133.14(16) . . ?
C7A C6A C5A 107.01(14) . . ?
N1A C7A C8A 130.34(15) . . ?
N1A C7A C6A 108.25(14) . . ?
C8A C7A C6A 121.41(15) . . ?
C9A C8A C7A 117.19(17) . . ?
C8A C9A C10A 121.92(17) . . ?
C11A C10A C9A 121.02(17) . . ?
C10A C11A C6A 118.61(17) . . ?
N2A C21A C31A 111.01(14) . . ?
N2A C21A C22A 102.75(13) . . ?
C31A C21A C22A 108.73(14) . . ?
N1A C22A C23A 115.33(14) . . ?
N1A C22A C21A 113.24(14) . . ?
C23A C22A C21A 101.21(13) . . ?
N3A C23A C24A 121.81(15) . . ?
N3A C23A C22A 112.83(15) . . ?
C24A C23A C22A 125.34(15) . . ?
C29A C24A C25A 118.00(19) . . ?
C29A C24A C23A 121.26(18) . . ?
C25A C24A C23A 120.73(16) . . ?
C26A C25A C24A 120.83(19) . . ?
C27A C26A C25A 120.4(2) . . ?
C28A C27A C26A 119.4(2) . . ?
C27A C28A C29A 120.9(2) . . ?
C28A C29A C24A 120.5(2) . . ?
O3A C31A C32A 121.62(16) . . ?
O3A C31A C21A 120.76(16) . . ?
C32A C31A C21A 117.52(14) . . ?
N4A C32A C33A 123.88(16) . . ?
N4A C32A C31A 116.16(15) . . ?
C33A C32A C31A 119.95(15) . . ?
C34A C33A C32A 118.71(17) . . ?
C35A C34A C33A 117.89(17) . . ?
C34A C35A C36A 119.53(17) . . ?
N4A C36A C35A 123.56(18) . . ?
C42A C41A N2A 119.35(16) . . ?
C42A C41A C46A 119.14(17) . . ?
N2A C41A C46A 121.50(16) . . ?
C43A C42A C41A 120.40(18) . . ?
C44A C43A C42A 120.6(2) . . ?
C43A C44A C45A 119.03(19) . . ?
C46A C45A C44A 121.27(19) . . ?
C45A C46A C41A 119.53(18) . . ?
C3B O1B C2B 115.35(15) . . ?
C7B N1B C4B 107.68(14) . . ?
C7B N1B C22B 125.35(14) . . ?
C4B N1B C22B 125.58(14) . . ?
N3B N2B C41B 120.88(14) . . ?
N3B N2B C21B 113.01(14) . . ?
C41B N2B C21B 125.08(15) . . ?
C23B N3B N2B 109.11(14) . . ?
C36B N4B C32B 117.25(18) . . ?
O1B C2B C1B 106.97(18) . . ?
O2B C3B O1B 123.49(16) . . ?
O2B C3B C4B 125.75(15) . . ?
O1B C3B C4B 110.76(15) . . ?
C5B C4B N1B 109.87(15) . . ?
C5B C4B C3B 127.26(16) . . ?
N1B C4B C3B 122.85(15) . . ?
C4B C5B C6B 107.36(16) . . ?
C11B C6B C7B 119.39(18) . . ?
C11B C6B C5B 133.64(19) . . ?
C7B C6B C5B 106.95(16) . . ?
N1B C7B C8B 130.23(17) . . ?
N1B C7B C6B 108.11(15) . . ?
C8B C7B C6B 121.66(17) . . ?
C9B C8B C7B 117.15(19) . . ?
C8B C9B C10B 122.1(2) . . ?
C11B C10B C9B 120.8(2) . . ?
C10B C11B C6B 118.9(2) . . ?
N2B C21B C31B 111.59(14) . . ?
N2B C21B C22B 102.43(13) . . ?
C31B C21B C22B 109.41(14) . . ?
N1B C22B C23B 113.85(14) . . ?
N1B C22B C21B 114.45(14) . . ?
C23B C22B C21B 100.86(13) . . ?
N3B C23B C24B 122.66(15) . . ?
N3B C23B C22B 113.49(15) . . ?
C24B C23B C22B 123.82(14) . . ?
C25B C24B C29B 119.02(16) . . ?
C25B C24B C23B 120.35(16) . . ?
C29B C24B C23B 120.63(16) . . ?
C26B C25B C24B 119.92(17) . . ?
C27B C26B C25B 120.44(19) . . ?
C26B C27B C28B 119.81(19) . . ?
C29B C28B C27B 120.54(18) . . ?
C28B C29B C24B 120.26(17) . . ?
O3B C31B C32B 122.60(17) . . ?
O3B C31B C21B 121.79(16) . . ?
C32B C31B C21B 115.60(15) . . ?
N4B C32B C33B 123.63(17) . . ?
N4B C32B C31B 115.56(16) . . ?
C33B C32B C31B 120.81(17) . . ?
C32B C33B C34B 118.0(2) . . ?
C35B C34B C33B 118.8(2) . . ?
C34B C35B C36B 118.95(19) . . ?
N4B C36B C35B 123.3(2) . . ?
N2B C41B C42B 121.01(16) . . ?
N2B C41B C46B 119.61(15) . . ?
C42B C41B C46B 119.37(16) . . ?
C43B C42B C41B 119.39(16) . . ?
C44B C43B C42B 121.50(17) . . ?
C45B C44B C43B 118.97(16) . . ?
C44B C45B C46B 120.85(18) . . ?
C45B C46B C41B 119.92(17) . . ?
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
O1A C3A 1.329(2) . ?
O1A C2A 1.442(2) . ?
O2X C3A 1.213(8) . ?
O2Y C3A 1.214(9) . ?
O3A C31A 1.211(2) . ?
N1A C7A 1.383(2) . ?
N1A C4A 1.396(2) . ?
N1A C22A 1.462(2) . ?
N2A N3A 1.362(2) . ?
N2A C41A 1.394(2) . ?
N2A C21A 1.459(2) . ?
N3A C23A 1.295(2) . ?
N4A C36A 1.334(2) . ?
N4A C32A 1.344(2) . ?
C1A C2A 1.495(3) . ?
C3A C4A 1.471(2) . ?
C4A C5A 1.372(2) . ?
C5A C6A 1.420(2) . ?
C6A C11A 1.408(2) . ?
C6A C7A 1.411(2) . ?
C7A C8A 1.405(2) . ?
C8A C9A 1.382(3) . ?
C9A C10A 1.405(3) . ?
C10A C11A 1.373(3) . ?
C21A C31A 1.530(2) . ?
C21A C22A 1.551(2) . ?
C22A C23A 1.526(2) . ?
C23A C24A 1.459(3) . ?
C24A C29A 1.390(3) . ?
C24A C25A 1.394(3) . ?
C25A C26A 1.382(3) . ?
C26A C27A 1.382(3) . ?
C27A C28A 1.365(4) . ?
C28A C29A 1.389(4) . ?
C31A C32A 1.498(2) . ?
C32A C33A 1.387(2) . ?
C33A C34A 1.387(3) . ?
C34A C35A 1.379(3) . ?
C35A C36A 1.386(3) . ?
C41A C42A 1.393(3) . ?
C41A C46A 1.396(2) . ?
C42A C43A 1.384(3) . ?
C43A C44A 1.380(3) . ?
C44A C45A 1.386(3) . ?
C45A C46A 1.384(3) . ?
O1B C3B 1.338(2) . ?
O1B C2B 1.456(2) . ?
O2B C3B 1.211(2) . ?
O3B C31B 1.205(2) . ?
N1B C7B 1.386(2) . ?
N1B C4B 1.395(2) . ?
N1B C22B 1.457(2) . ?
N2B N3B 1.372(2) . ?
N2B C41B 1.389(2) . ?
N2B C21B 1.453(2) . ?
N3B C23B 1.289(2) . ?
N4B C36B 1.333(3) . ?
N4B C32B 1.338(3) . ?
C1B C2B 1.508(3) . ?
C3B C4B 1.472(2) . ?
C4B C5B 1.365(3) . ?
C5B C6B 1.426(3) . ?
C6B C11B 1.408(3) . ?
C6B C7B 1.412(3) . ?
C7B C8B 1.403(3) . ?
C8B C9B 1.375(3) . ?
C9B C10B 1.408(4) . ?
C10B C11B 1.370(4) . ?
C21B C31B 1.533(2) . ?
C21B C22B 1.557(2) . ?
C22B C23B 1.522(2) . ?
C23B C24B 1.464(2) . ?
C24B C25B 1.398(2) . ?
C24B C29B 1.399(2) . ?
C25B C26B 1.393(3) . ?
C26B C27B 1.381(3) . ?
C27B C28B 1.383(3) . ?
C28B C29B 1.383(3) . ?
C31B C32B 1.500(2) . ?
C32B C33B 1.386(3) . ?
C33B C34B 1.390(3) . ?
C34B C35B 1.375(4) . ?
C35B C36B 1.384(3) . ?
C41B C42B 1.395(2) . ?
C41B C46B 1.400(3) . ?
C42B C43B 1.386(2) . ?
C43B C44B 1.383(3) . ?
C44B C45B 1.380(3) . ?
C45B C46B 1.387(3) . ?
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
C41A N2A N3A C23A 165.32(16) . . . . ?
C21A N2A N3A C23A -2.5(2) . . . . ?
C3A O1A C2A C1A -178.2(2) . . . . ?
C2A O1A C3A O2X -18(3) . . . . ?
C2A O1A C3A O2Y 14.9(13) . . . . ?
C2A O1A C3A C4A 176.15(19) . . . . ?
C7A N1A C4A C5A -2.0(2) . . . . ?
C22A N1A C4A C5A -172.43(16) . . . . ?
C7A N1A C4A C3A 175.42(17) . . . . ?
C22A N1A C4A C3A 5.0(3) . . . . ?
O2X C3A C4A C5A -166(3) . . . . ?
O2Y C3A C4A C5A 160.2(12) . . . . ?
O1A C3A C4A C5A -1.1(3) . . . . ?
O2X C3A C4A N1A 17(3) . . . . ?
O2Y C3A C4A N1A -16.8(12) . . . . ?
O1A C3A C4A N1A -178.02(17) . . . . ?
N1A C4A C5A C6A 1.3(2) . . . . ?
C3A C4A C5A C6A -176.05(18) . . . . ?
C4A C5A C6A C11A 179.28(19) . . . . ?
C4A C5A C6A C7A -0.1(2) . . . . ?
C4A N1A C7A C8A -178.06(19) . . . . ?
C22A N1A C7A C8A -7.6(3) . . . . ?
C4A N1A C7A C6A 1.89(19) . . . . ?
C22A N1A C7A C6A 172.34(16) . . . . ?
C11A C6A C7A N1A 179.41(16) . . . . ?
C5A C6A C7A N1A -1.13(19) . . . . ?
C11A C6A C7A C8A -0.6(3) . . . . ?
C5A C6A C7A C8A 178.82(17) . . . . ?
N1A C7A C8A C9A -179.37(18) . . . . ?
C6A C7A C8A C9A 0.7(3) . . . . ?
C7A C8A C9A C10A -0.4(3) . . . . ?
C8A C9A C10A C11A 0.1(3) . . . . ?
C9A C10A C11A C6A 0.0(3) . . . . ?
C7A C6A C11A C10A 0.3(3) . . . . ?
C5A C6A C11A C10A -179.0(2) . . . . ?
N3A N2A C21A C31A -111.33(17) . . . . ?
C41A N2A C21A C31A 81.0(2) . . . . ?
N3A N2A C21A C22A 4.74(18) . . . . ?
C41A N2A C21A C22A -162.89(16) . . . . ?
C7A N1A C22A C23A 51.8(2) . . . . ?
C4A N1A C22A C23A -139.40(17) . . . . ?
C7A N1A C22A C21A -64.1(2) . . . . ?
C4A N1A C22A C21A 104.67(19) . . . . ?
N2A C21A C22A N1A 119.34(15) . . . . ?
C31A C21A C22A N1A -122.95(15) . . . . ?
N2A C21A C22A C23A -4.69(16) . . . . ?
C31A C21A C22A C23A 113.01(14) . . . . ?
N2A N3A C23A C24A 177.41(15) . . . . ?
N2A N3A C23A C22A -1.02(19) . . . . ?
N1A C22A C23A N3A -118.83(16) . . . . ?
C21A C22A C23A N3A 3.77(18) . . . . ?
N1A C22A C23A C24A 62.8(2) . . . . ?
C21A C22A C23A C24A -174.59(15) . . . . ?
N3A C23A C24A C29A 172.9(2) . . . . ?
C22A C23A C24A C29A -8.9(3) . . . . ?
N3A C23A C24A C25A -6.0(3) . . . . ?
C22A C23A C24A C25A 172.18(16) . . . . ?
C29A C24A C25A C26A -2.5(3) . . . . ?
C23A C24A C25A C26A 176.43(17) . . . . ?
C24A C25A C26A C27A 0.7(3) . . . . ?
C25A C26A C27A C28A 1.2(4) . . . . ?
C26A C27A C28A C29A -1.3(5) . . . . ?
C27A C28A C29A C24A -0.6(5) . . . . ?
C25A C24A C29A C28A 2.5(4) . . . . ?
C23A C24A C29A C28A -176.5(2) . . . . ?
N2A C21A C31A O3A 28.5(3) . . . . ?
C22A C21A C31A O3A -83.8(2) . . . . ?
N2A C21A C31A C32A -155.15(15) . . . . ?
C22A C21A C31A C32A 92.53(18) . . . . ?
C36A N4A C32A C33A 0.4(3) . . . . ?
C36A N4A C32A C31A -179.62(17) . . . . ?
O3A C31A C32A N4A -169.81(19) . . . . ?
C21A C31A C32A N4A 13.8(2) . . . . ?
O3A C31A C32A C33A 10.1(3) . . . . ?
C21A C31A C32A C33A -166.22(16) . . . . ?
N4A C32A C33A C34A -0.9(3) . . . . ?
C31A C32A C33A C34A 179.15(16) . . . . ?
C32A C33A C34A C35A 0.2(3) . . . . ?
C33A C34A C35A C36A 0.9(3) . . . . ?
C32A N4A C36A C35A 0.7(3) . . . . ?
C34A C35A C36A N4A -1.4(3) . . . . ?
N3A N2A C41A C42A 177.70(17) . . . . ?
C21A N2A C41A C42A -15.7(3) . . . . ?
N3A N2A C41A C46A -2.9(3) . . . . ?
C21A N2A C41A C46A 163.70(17) . . . . ?
N2A C41A C42A C43A 178.02(19) . . . . ?
C46A C41A C42A C43A -1.4(3) . . . . ?
C41A C42A C43A C44A 0.9(3) . . . . ?
C42A C43A C44A C45A 0.5(4) . . . . ?
C43A C44A C45A C46A -1.4(4) . . . . ?
C44A C45A C46A C41A 0.8(3) . . . . ?
C42A C41A C46A C45A 0.6(3) . . . . ?
N2A C41A C46A C45A -178.86(19) . . . . ?
C41B N2B N3B C23B -177.44(16) . . . . ?
C21B N2B N3B C23B -8.5(2) . . . . ?
C3B O1B C2B C1B 172.17(17) . . . . ?
C2B O1B C3B O2B -1.0(3) . . . . ?
C2B O1B C3B C4B 179.31(15) . . . . ?
C7B N1B C4B C5B -1.5(2) . . . . ?
C22B N1B C4B C5B -168.59(15) . . . . ?
C7B N1B C4B C3B 179.80(16) . . . . ?
C22B N1B C4B C3B 12.7(3) . . . . ?
O2B C3B C4B C5B -164.63(19) . . . . ?
O1B C3B C4B C5B 15.0(3) . . . . ?
O2B C3B C4B N1B 13.8(3) . . . . ?
O1B C3B C4B N1B -166.49(16) . . . . ?
N1B C4B C5B C6B 1.0(2) . . . . ?
C3B C4B C5B C6B 179.65(17) . . . . ?
C4B C5B C6B C11B 178.6(2) . . . . ?
C4B C5B C6B C7B -0.2(2) . . . . ?
C4B N1B C7B C8B -178.02(19) . . . . ?
C22B N1B C7B C8B -10.9(3) . . . . ?
C4B N1B C7B C6B 1.36(19) . . . . ?
C22B N1B C7B C6B 168.50(15) . . . . ?
C11B C6B C7B N1B -179.69(18) . . . . ?
C5B C6B C7B N1B -0.8(2) . . . . ?
C11B C6B C7B C8B -0.2(3) . . . . ?
C5B C6B C7B C8B 178.70(18) . . . . ?
N1B C7B C8B C9B 179.8(2) . . . . ?
C6B C7B C8B C9B 0.5(3) . . . . ?
C7B C8B C9B C10B -0.7(3) . . . . ?
C8B C9B C10B C11B 0.7(4) . . . . ?
C9B C10B C11B C6B -0.4(4) . . . . ?
C7B C6B C11B C10B 0.1(3) . . . . ?
C5B C6B C11B C10B -178.4(2) . . . . ?
N3B N2B C21B C31B -106.06(17) . . . . ?
C41B N2B C21B C31B 62.3(2) . . . . ?
N3B N2B C21B C22B 10.89(19) . . . . ?
C41B N2B C21B C22B 179.28(16) . . . . ?
C7B N1B C22B C23B 56.9(2) . . . . ?
C4B N1B C22B C23B -138.25(16) . . . . ?
C7B N1B C22B C21B -58.4(2) . . . . ?
C4B N1B C22B C21B 106.45(18) . . . . ?
N2B C21B C22B N1B 114.03(15) . . . . ?
C31B C21B C22B N1B -127.47(15) . . . . ?
N2B C21B C22B C23B -8.62(16) . . . . ?
C31B C21B C22B C23B 109.87(15) . . . . ?
N2B N3B C23B C24B -176.41(15) . . . . ?
N2B N3B C23B C22B 1.9(2) . . . . ?
N1B C22B C23B N3B -118.44(16) . . . . ?
C21B C22B C23B N3B 4.63(19) . . . . ?
N1B C22B C23B C24B 59.8(2) . . . . ?
C21B C22B C23B C24B -177.10(16) . . . . ?
N3B C23B C24B C25B -166.05(17) . . . . ?
C22B C23B C24B C25B 15.8(3) . . . . ?
N3B C23B C24B C29B 14.6(3) . . . . ?
C22B C23B C24B C29B -163.55(16) . . . . ?
C29B C24B C25B C26B 0.5(3) . . . . ?
C23B C24B C25B C26B -178.88(17) . . . . ?
C24B C25B C26B C27B 0.5(3) . . . . ?
C25B C26B C27B C28B -1.1(3) . . . . ?
C26B C27B C28B C29B 0.6(3) . . . . ?
C27B C28B C29B C24B 0.4(3) . . . . ?
C25B C24B C29B C28B -0.9(3) . . . . ?
C23B C24B C29B C28B 178.45(17) . . . . ?
N2B C21B C31B O3B 13.4(3) . . . . ?
C22B C21B C31B O3B -99.2(2) . . . . ?
N2B C21B C31B C32B -168.01(15) . . . . ?
C22B C21B C31B C32B 79.36(19) . . . . ?
C36B N4B C32B C33B -0.4(3) . . . . ?
C36B N4B C32B C31B 179.93(18) . . . . ?
O3B C31B C32B N4B 176.85(19) . . . . ?
C21B C31B C32B N4B -1.7(2) . . . . ?
O3B C31B C32B C33B -2.8(3) . . . . ?
C21B C31B C32B C33B 178.67(18) . . . . ?
N4B C32B C33B C34B 1.3(3) . . . . ?
C31B C32B C33B C34B -179.09(19) . . . . ?
C32B C33B C34B C35B -0.2(3) . . . . ?
C33B C34B C35B C36B -1.6(3) . . . . ?
C32B N4B C36B C35B -1.5(3) . . . . ?
C34B C35B C36B N4B 2.6(3) . . . . ?
N3B N2B C41B C42B -3.5(3) . . . . ?
C21B N2B C41B C42B -170.99(17) . . . . ?
N3B N2B C41B C46B 177.99(17) . . . . ?
C21B N2B C41B C46B 10.5(3) . . . . ?
N2B C41B C42B C43B -178.31(17) . . . . ?
C46B C41B C42B C43B 0.3(3) . . . . ?
C41B C42B C43B C44B -0.6(3) . . . . ?
C42B C43B C44B C45B 0.3(3) . . . . ?
C43B C44B C45B C46B 0.4(3) . . . . ?
C44B C45B C46B C41B -0.7(3) . . . . ?
N2B C41B C46B C45B 178.97(17) . . . . ?
C42B C41B C46B C45B 0.4(3) . . . . ?
