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#$Date: 2024-03-04 21:47:46 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290081 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/26/7132678.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_7132678
loop_
_publ_author_name
'Yu, Jiulong'
'Wu, Jinyu'
'Zhu, Yu'
'Xiong, Dong'
'Yang, Lin'
'Li, Jun'
'Zheng, Jianfeng'
_publ_section_title
;
 Chiral phosphoric acid-catalyzed enantioselective [5+1] cycloaddition
 reaction of C,N-cyclic azomethine imines with isocyanides.
;
_journal_issue                   19
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2637
_journal_page_last               2640
_journal_paper_doi               10.1039/d3cc05890e
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H22 Cl2 N4 O'
_chemical_formula_sum            'C27 H22 Cl2 N4 O'
_chemical_formula_weight         489.38
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-06-21 deposited with the CCDC.	2024-02-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.6860(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1692(2)
_cell_length_b                   9.7507(2)
_cell_length_c                   23.6934(5)
_cell_measurement_reflns_used    9779
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      3.81
_cell_volume                     2300.67(8)
_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 0.995
_diffrn_measured_fraction_theta_max 0.996
_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  0.0561
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            42371
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.248
_diffrn_reflns_theta_min         3.810
_exptl_absorpt_coefficient_mu    2.767
_exptl_absorpt_correction_T_max  0.9310
_exptl_absorpt_correction_T_min  0.4124
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.549
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.101
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
; 
 Flack x determined using 3256 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.048(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     621
_refine_ls_number_reflns         8210
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0329
_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)+(0.0345P)²+0.4919P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0759
_refine_ls_wR_factor_ref         0.0783
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    0.953
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                7704
_reflns_number_total             8210
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc05890e2.cif
_cod_data_source_block           zjf020
_cod_depositor_comments
'Adding full bibliography for 7132675--7132678.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7132678
_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   0.312
_shelx_estimated_absorpt_t_max   0.767
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
O1A O 0.34858(18) 0.3229(2) 0.40919(8) 0.0252(4) Uani 1 1 d . . . . .
N1A N -0.0773(3) 0.5756(3) 0.45708(11) 0.0371(7) Uani 1 1 d D . . . .
H1NA H -0.119(5) 0.627(5) 0.479(2) 0.072(16) Uiso 1 1 d D . . . .
N2A N 0.2121(2) 0.1823(3) 0.44960(9) 0.0227(5) Uani 1 1 d . . . . .
N3A N 0.5600(2) 0.2172(2) 0.48285(9) 0.0215(4) Uani 1 1 d . . . . .
N4A N 0.5814(2) 0.3232(3) 0.44633(9) 0.0221(5) Uani 1 1 d . . . . .
C1A C 0.1140(3) 0.1829(3) 0.39463(11) 0.0265(6) Uani 1 1 d . . . . .
H1AA H 0.107704 0.089634 0.377760 0.032 Uiso 1 1 calc R U . . .
H1AB H 0.145354 0.245781 0.367318 0.032 Uiso 1 1 calc R U . . .
C2A C -0.0244(3) 0.2281(4) 0.40264(12) 0.0309(7) Uani 1 1 d . . . . .
H2AA H -0.090965 0.204822 0.367336 0.037 Uiso 1 1 calc R U . . .
H2AB H -0.047904 0.175266 0.434885 0.037 Uiso 1 1 calc R U . . .
C3A C -0.0356(3) 0.3775(4) 0.41473(12) 0.0279(6) Uani 1 1 d . . . . .
C4A C -0.0689(3) 0.4358(4) 0.46229(13) 0.0352(8) Uani 1 1 d . . . . .
H4A H -0.084351 0.385924 0.494773 0.042 Uiso 1 1 calc R U . . .
C5A C -0.0253(3) 0.4895(3) 0.37631(11) 0.0250(6) Uani 1 1 d . . . . .
C6A C -0.0523(3) 0.6119(4) 0.40387(12) 0.0291(6) Uani 1 1 d . . . . .
C7A C -0.0543(3) 0.7403(4) 0.37781(13) 0.0334(7) Uani 1 1 d . . . . .
H7A H -0.071477 0.821888 0.396978 0.040 Uiso 1 1 calc R U . . .
C8A C -0.0300(3) 0.7421(3) 0.32259(14) 0.0315(6) Uani 1 1 d . . . . .
C9A C -0.0053(3) 0.6237(3) 0.29331(12) 0.0294(6) Uani 1 1 d . . . . .
H9A H 0.009163 0.629953 0.255018 0.035 Uiso 1 1 calc R U . . .
Cl1A Cl -0.03230(10) 0.89901(10) 0.28706(4) 0.0498(2) Uani 1 1 d . . . . .
Cl2A Cl 0.52030(10) 0.80768(9) 0.24050(3) 0.0458(2) Uani 1 1 d . . . . .
C10A C -0.0020(3) 0.4972(3) 0.32005(12) 0.0262(6) Uani 1 1 d . . . . .
H10A H 0.015839 0.416458 0.300485 0.031 Uiso 1 1 calc R U . . .
C11A C 0.3225(3) 0.2429(3) 0.45334(11) 0.0202(5) Uani 1 1 d . . . . .
C12A C 0.4360(3) 0.2312(3) 0.50524(11) 0.0217(5) Uani 1 1 d . . . . .
H12A H 0.422938 0.143095 0.525003 0.026 Uiso 1 1 calc R U . . .
C13A C 0.4435(3) 0.3453(3) 0.54993(11) 0.0210(5) Uani 1 1 d . . . . .
C14A C 0.3271(3) 0.4024(3) 0.56292(12) 0.0270(6) Uani 1 1 d . . . . .
H14A H 0.241801 0.377016 0.540919 0.032 Uiso 1 1 calc R U . . .
C15A C 0.3349(3) 0.4957(4) 0.60757(13) 0.0334(7) Uani 1 1 d . . . . .
H15A H 0.255244 0.533922 0.616107 0.040 Uiso 1 1 calc R U . . .
C16A C 0.4590(3) 0.5333(3) 0.63975(13) 0.0319(6) Uani 1 1 d . . . . .
H16A H 0.464595 0.596493 0.670669 0.038 Uiso 1 1 calc R U . . .
C17A C 0.5744(3) 0.4786(3) 0.62671(12) 0.0284(6) Uani 1 1 d . . . . .
H17A H 0.659284 0.505798 0.648598 0.034 Uiso 1 1 calc R U . . .
C18A C 0.5691(3) 0.3843(3) 0.58211(11) 0.0236(5) Uani 1 1 d . . . . .
C19A C 0.6981(3) 0.3280(3) 0.56856(12) 0.0270(6) Uani 1 1 d . . . . .
H19A H 0.759894 0.303816 0.605127 0.032 Uiso 1 1 calc R U . . .
H19B H 0.741761 0.400591 0.549598 0.032 Uiso 1 1 calc R U . . .
C20A C 0.6769(3) 0.2024(3) 0.52981(11) 0.0243(5) Uani 1 1 d . . . . .
H20A H 0.757858 0.187272 0.513418 0.029 Uiso 1 1 calc R U . . .
H20B H 0.664673 0.120834 0.553107 0.029 Uiso 1 1 calc R U . . .
C21A C 0.4789(3) 0.3691(3) 0.41179(11) 0.0212(5) Uani 1 1 d . . . . .
C22A C 0.4872(3) 0.4746(3) 0.36846(11) 0.0212(5) Uani 1 1 d . . . . .
C23A C 0.3737(3) 0.5476(3) 0.34153(11) 0.0239(6) Uani 1 1 d . . . . .
H23A H 0.288444 0.525450 0.349609 0.029 Uiso 1 1 calc R U . . .
C24A C 0.3844(3) 0.6521(3) 0.30315(11) 0.0268(6) Uani 1 1 d . . . . .
H24A H 0.307589 0.704010 0.286020 0.032 Uiso 1 1 calc R U . . .
C25A C 0.5081(3) 0.6798(3) 0.29007(11) 0.0299(6) Uani 1 1 d . . . . .
C26A C 0.6214(3) 0.6068(4) 0.31520(12) 0.0347(7) Uani 1 1 d . . . . .
H26A H 0.705461 0.626563 0.305393 0.042 Uiso 1 1 calc R U . . .
C27A C 0.6115(3) 0.5048(3) 0.35473(12) 0.0302(6) Uani 1 1 d . . . . .
H27A H 0.689303 0.455289 0.372591 0.036 Uiso 1 1 calc R U . . .
O1B O 0.43491(18) 0.6914(2) 0.09225(7) 0.0242(4) Uani 1 1 d . . . . .
N1B N -0.0356(3) 0.4293(4) 0.04218(11) 0.0384(7) Uani 1 1 d D . . . .
H1NB H -0.095(4) 0.377(4) 0.0194(16) 0.051(12) Uiso 1 1 d D . . . .
N2B N 0.2563(2) 0.8275(2) 0.05190(9) 0.0221(4) Uani 1 1 d . . . . .
N3B N 0.6297(2) 0.6876(2) 0.05306(9) 0.0213(4) Uani 1 1 d . . . . .
N4B N 0.5733(2) 0.7946(2) 0.01732(9) 0.0210(4) Uani 1 1 d . . . . .
C1B C 0.2113(3) 0.8234(3) 0.10728(11) 0.0271(6) Uani 1 1 d . . . . .
H1BA H 0.219803 0.916011 0.124742 0.032 Uiso 1 1 calc R U . . .
H1BB H 0.269891 0.760409 0.133992 0.032 Uiso 1 1 calc R U . . .
C2B C 0.0659(3) 0.7755(3) 0.09954(13) 0.0312(7) Uani 1 1 d . . . . .
H2BA H 0.033593 0.795502 0.135374 0.037 Uiso 1 1 calc R U . . .
H2BB H 0.010399 0.829511 0.068132 0.037 Uiso 1 1 calc R U . . .
C3B C 0.0449(3) 0.6277(4) 0.08599(12) 0.0293(7) Uani 1 1 d . . . . .
C4B C -0.0333(3) 0.5694(4) 0.03816(13) 0.0365(8) Uani 1 1 d . . . . .
H4B H -0.080163 0.619935 0.006043 0.044 Uiso 1 1 calc R U . . .
C5B C 0.0934(3) 0.5139(3) 0.12290(12) 0.0261(6) Uani 1 1 d . . . . .
C6B C 0.0404(3) 0.3912(4) 0.09468(12) 0.0302(7) Uani 1 1 d . . . . .
C7B C 0.0646(3) 0.2630(4) 0.12024(14) 0.0336(7) Uani 1 1 d . . . . .
H7B H 0.029847 0.181585 0.100754 0.040 Uiso 1 1 calc R U . . .
C8B C 0.1416(3) 0.2597(3) 0.17521(13) 0.0321(7) Uani 1 1 d . . . . .
C9B C 0.1954(3) 0.3780(4) 0.20491(12) 0.0298(6) Uani 1 1 d . . . . .
H9B H 0.247616 0.370994 0.242874 0.036 Uiso 1 1 calc R U . . .
Cl1B Cl 0.17246(11) 0.10256(10) 0.21073(4) 0.0536(2) Uani 1 1 d . . . . .
Cl2B Cl 0.75425(9) 0.19838(9) 0.25847(3) 0.04161(19) Uani 1 1 d . . . . .
C10B C 0.1721(3) 0.5040(3) 0.17882(12) 0.0278(6) Uani 1 1 d . . . . .
H10B H 0.209144 0.584263 0.198563 0.033 Uiso 1 1 calc R U . . .
C11B C 0.3650(3) 0.7698(3) 0.04791(11) 0.0192(5) Uani 1 1 d . . . . .
C12B C 0.4275(2) 0.7819(3) -0.00412(11) 0.0196(5) Uani 1 1 d . . . . .
H12B H 0.395633 0.870257 -0.023623 0.023 Uiso 1 1 calc R U . . .
C13B C 0.3905(3) 0.6679(3) -0.04871(11) 0.0200(5) Uani 1 1 d . . . . .
C14B C 0.2624(3) 0.6108(3) -0.06029(11) 0.0248(6) Uani 1 1 d . . . . .
H14B H 0.199532 0.636228 -0.037464 0.030 Uiso 1 1 calc R U . . .
C15B C 0.2255(3) 0.5172(3) -0.10482(13) 0.0297(6) Uani 1 1 d . . . . .
H15B H 0.137777 0.478835 -0.112389 0.036 Uiso 1 1 calc R U . . .
C16B C 0.3167(3) 0.4800(3) -0.13814(12) 0.0301(6) Uani 1 1 d . . . . .
H16B H 0.291478 0.416863 -0.168982 0.036 Uiso 1 1 calc R U . . .
C17B C 0.4448(3) 0.5349(3) -0.12644(12) 0.0270(6) Uani 1 1 d . . . . .
H17B H 0.507343 0.507665 -0.149120 0.032 Uiso 1 1 calc R U . . .
C18B C 0.4839(3) 0.6293(3) -0.08200(11) 0.0215(5) Uani 1 1 d . . . . .
C19B C 0.6262(3) 0.6844(3) -0.06975(12) 0.0266(6) Uani 1 1 d . . . . .
H19C H 0.651632 0.708604 -0.106691 0.032 Uiso 1 1 calc R U . . .
H19D H 0.687951 0.611355 -0.051349 0.032 Uiso 1 1 calc R U . . .
C20B C 0.6437(3) 0.8099(3) -0.03076(11) 0.0248(5) Uani 1 1 d . . . . .
H20C H 0.740533 0.824813 -0.015170 0.030 Uiso 1 1 calc R U . . .
H20D H 0.608582 0.891670 -0.053715 0.030 Uiso 1 1 calc R U . . .
C21B C 0.5612(3) 0.6431(3) 0.08866(11) 0.0201(5) Uani 1 1 d . . . . .
C22B C 0.6089(3) 0.5368(3) 0.13161(11) 0.0206(5) Uani 1 1 d . . . . .
C23B C 0.5228(3) 0.4769(3) 0.16338(12) 0.0259(6) Uani 1 1 d . . . . .
H23B H 0.432631 0.507884 0.158288 0.031 Uiso 1 1 calc R U . . .
C24B C 0.5674(3) 0.3728(3) 0.20233(12) 0.0289(6) Uani 1 1 d . . . . .
H24B H 0.507888 0.331419 0.223485 0.035 Uiso 1 1 calc R U . . .
C25B C 0.6988(3) 0.3300(3) 0.21003(11) 0.0278(6) Uani 1 1 d . . . . .
C26B C 0.7867(3) 0.3883(4) 0.17959(12) 0.0314(7) Uani 1 1 d . . . . .
H26B H 0.877087 0.357534 0.185434 0.038 Uiso 1 1 calc R U . . .
C27B C 0.7421(3) 0.4923(3) 0.14033(12) 0.0280(6) Uani 1 1 d . . . . .
H27B H 0.802183 0.533296 0.119387 0.034 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'
Cl Cl 0.3639 0.7018 '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
C11A O1A C21A 118.7(2) . . ?
C4A N1A C6A 108.5(3) . . ?
C11A N2A C1A 119.8(2) . . ?
N4A N3A C20A 109.9(2) . . ?
N4A N3A C12A 114.1(2) . . ?
C20A N3A C12A 111.1(2) . . ?
C21A N4A N3A 116.8(2) . . ?
N2A C1A C2A 111.7(2) . . ?
C3A C2A C1A 114.5(2) . . ?
C4A C3A C5A 105.6(3) . . ?
C4A C3A C2A 127.3(3) . . ?
C5A C3A C2A 126.9(3) . . ?
C3A C4A N1A 111.2(3) . . ?
C10A C5A C6A 118.6(3) . . ?
C10A C5A C3A 133.7(3) . . ?
C6A C5A C3A 107.6(2) . . ?
N1A C6A C7A 130.2(3) . . ?
N1A C6A C5A 107.1(3) . . ?
C7A C6A C5A 122.7(2) . . ?
C8A C7A C6A 116.2(3) . . ?
C7A C8A C9A 123.1(3) . . ?
C7A C8A Cl1A 118.8(3) . . ?
C9A C8A Cl1A 118.2(2) . . ?
C10A C9A C8A 120.0(3) . . ?
C9A C10A C5A 119.4(3) . . ?
N2A C11A O1A 121.4(2) . . ?
N2A C11A C12A 123.1(2) . . ?
O1A C11A C12A 115.5(2) . . ?
N3A C12A C11A 106.4(2) . . ?
N3A C12A C13A 113.1(2) . . ?
C11A C12A C13A 115.6(2) . . ?
C14A C13A C18A 119.4(3) . . ?
C14A C13A C12A 121.2(2) . . ?
C18A C13A C12A 119.1(2) . . ?
C15A C14A C13A 120.6(3) . . ?
C16A C15A C14A 120.0(3) . . ?
C17A C16A C15A 119.7(3) . . ?
C16A C17A C18A 121.4(3) . . ?
C17A C18A C13A 118.9(3) . . ?
C17A C18A C19A 119.8(3) . . ?
C13A C18A C19A 121.3(3) . . ?
C18A C19A C20A 113.4(2) . . ?
N3A C20A C19A 112.0(2) . . ?
N4A C21A O1A 124.5(2) . . ?
N4A C21A C22A 122.8(2) . . ?
O1A C21A C22A 112.7(2) . . ?
C23A C22A C27A 119.2(3) . . ?
C23A C22A C21A 121.2(2) . . ?
C27A C22A C21A 119.5(2) . . ?
C24A C23A C22A 120.6(3) . . ?
C25A C24A C23A 119.2(3) . . ?
C24A C25A C26A 121.3(3) . . ?
C24A C25A Cl2A 119.1(2) . . ?
C26A C25A Cl2A 119.6(2) . . ?
C25A C26A C27A 119.6(3) . . ?
C26A C27A C22A 120.1(3) . . ?
C11B O1B C21B 118.9(2) . . ?
C4B N1B C6B 108.5(3) . . ?
C11B N2B C1B 119.3(2) . . ?
C21B N3B N4B 116.4(2) . . ?
N3B N4B C20B 110.0(2) . . ?
N3B N4B C12B 114.1(2) . . ?
C20B N4B C12B 110.83(19) . . ?
N2B C1B C2B 111.7(2) . . ?
C3B C2B C1B 114.7(2) . . ?
C4B C3B C5B 104.6(3) . . ?
C4B C3B C2B 128.1(3) . . ?
C5B C3B C2B 127.0(3) . . ?
C3B C4B N1B 111.9(3) . . ?
C10B C5B C6B 118.3(3) . . ?
C10B C5B C3B 133.4(3) . . ?
C6B C5B C3B 108.2(2) . . ?
N1B C6B C7B 130.9(3) . . ?
N1B C6B C5B 106.7(3) . . ?
C7B C6B C5B 122.3(3) . . ?
C8B C7B C6B 116.7(3) . . ?
C7B C8B C9B 123.0(3) . . ?
C7B C8B Cl1B 119.2(3) . . ?
C9B C8B Cl1B 117.8(2) . . ?
C10B C9B C8B 119.7(3) . . ?
C9B C10B C5B 119.9(3) . . ?
N2B C11B O1B 121.1(2) . . ?
N2B C11B C12B 123.3(2) . . ?
O1B C11B C12B 115.6(2) . . ?
N4B C12B C11B 106.7(2) . . ?
N4B C12B C13B 112.9(2) . . ?
C11B C12B C13B 115.1(2) . . ?
C14B C13B C18B 119.7(3) . . ?
C14B C13B C12B 121.1(2) . . ?
C18B C13B C12B 119.0(2) . . ?
C15B C14B C13B 120.7(3) . . ?
C16B C15B C14B 119.8(3) . . ?
C15B C16B C17B 119.8(3) . . ?
C16B C17B C18B 121.3(3) . . ?
C17B C18B C13B 118.7(2) . . ?
C17B C18B C19B 119.6(2) . . ?
C13B C18B C19B 121.8(2) . . ?
C18B C19B C20B 113.0(2) . . ?
N4B C20B C19B 111.9(2) . . ?
N3B C21B O1B 124.2(2) . . ?
N3B C21B C22B 123.5(2) . . ?
O1B C21B C22B 112.2(2) . . ?
C23B C22B C27B 119.1(3) . . ?
C23B C22B C21B 121.1(2) . . ?
C27B C22B C21B 119.8(2) . . ?
C24B C23B C22B 120.7(3) . . ?
C25B C24B C23B 119.2(3) . . ?
C24B C25B C26B 121.3(3) . . ?
C24B C25B Cl2B 119.2(2) . . ?
C26B C25B Cl2B 119.5(2) . . ?
C25B C26B C27B 119.5(3) . . ?
C26B C27B C22B 120.1(3) . . ?
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 C11A 1.373(3) . ?
O1A C21A 1.389(3) . ?
N1A C4A 1.370(5) . ?
N1A C6A 1.382(4) . ?
N2A C11A 1.256(4) . ?
N2A C1A 1.472(3) . ?
N3A N4A 1.393(3) . ?
N3A C20A 1.462(3) . ?
N3A C12A 1.470(3) . ?
N4A C21A 1.269(4) . ?
C1A C2A 1.523(4) . ?
C2A C3A 1.494(5) . ?
C3A C4A 1.365(4) . ?
C3A C5A 1.439(4) . ?
C5A C10A 1.402(4) . ?
C5A C6A 1.414(5) . ?
C6A C7A 1.394(5) . ?
C7A C8A 1.380(5) . ?
C8A C9A 1.395(5) . ?
C8A Cl1A 1.744(3) . ?
C9A C10A 1.384(5) . ?
Cl2A C25A 1.734(3) . ?
C11A C12A 1.511(4) . ?
C12A C13A 1.527(4) . ?
C13A C14A 1.397(4) . ?
C13A C18A 1.401(4) . ?
C14A C15A 1.385(4) . ?
C15A C16A 1.385(5) . ?
C16A C17A 1.380(5) . ?
C17A C18A 1.393(4) . ?
C18A C19A 1.516(4) . ?
C19A C20A 1.520(4) . ?
C21A C22A 1.468(4) . ?
C22A C23A 1.396(4) . ?
C22A C27A 1.399(4) . ?
C23A C24A 1.384(4) . ?
C24A C25A 1.382(4) . ?
C25A C26A 1.383(5) . ?
C26A C27A 1.384(4) . ?
O1B C11B 1.375(3) . ?
O1B C21B 1.386(3) . ?
N1B C4B 1.370(5) . ?
N1B C6B 1.376(4) . ?
N2B C11B 1.261(4) . ?
N2B C1B 1.475(3) . ?
N3B C21B 1.274(4) . ?
N3B N4B 1.392(3) . ?
N4B C20B 1.470(3) . ?
N4B C12B 1.472(3) . ?
C1B C2B 1.525(4) . ?
C2B C3B 1.482(5) . ?
C3B C4B 1.369(4) . ?
C3B C5B 1.438(4) . ?
C5B C10B 1.406(4) . ?
C5B C6B 1.423(4) . ?
C6B C7B 1.389(5) . ?
C7B C8B 1.377(5) . ?
C8B C9B 1.403(5) . ?
C8B Cl1B 1.746(3) . ?
C9B C10B 1.374(5) . ?
Cl2B C25B 1.737(3) . ?
C11B C12B 1.501(3) . ?
C12B C13B 1.527(4) . ?
C13B C14B 1.392(4) . ?
C13B C18B 1.403(4) . ?
C14B C15B 1.388(4) . ?
C15B C16B 1.383(4) . ?
C16B C17B 1.383(4) . ?
C17B C18B 1.395(4) . ?
C18B C19B 1.516(4) . ?
C19B C20B 1.522(4) . ?
C21B C22B 1.465(4) . ?
C22B C23B 1.392(4) . ?
C22B C27B 1.397(4) . ?
C23B C24B 1.385(4) . ?
C24B C25B 1.377(4) . ?
C25B C26B 1.380(4) . ?
C26B C27B 1.389(4) . ?
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
C20A N3A N4A C21A -164.2(2) . . . . ?
C12A N3A N4A C21A -38.6(3) . . . . ?
C11A N2A C1A C2A -128.9(3) . . . . ?
N2A C1A C2A C3A 72.5(3) . . . . ?
C1A C2A C3A C4A -120.0(3) . . . . ?
C1A C2A C3A C5A 66.0(4) . . . . ?
C5A C3A C4A N1A -1.3(3) . . . . ?
C2A C3A C4A N1A -176.3(3) . . . . ?
C6A N1A C4A C3A 1.6(4) . . . . ?
C4A C3A C5A C10A -175.7(3) . . . . ?
C2A C3A C5A C10A -0.7(5) . . . . ?
C4A C3A C5A C6A 0.6(3) . . . . ?
C2A C3A C5A C6A 175.6(3) . . . . ?
C4A N1A C6A C7A 177.2(3) . . . . ?
C4A N1A C6A C5A -1.1(3) . . . . ?
C10A C5A C6A N1A 177.3(3) . . . . ?
C3A C5A C6A N1A 0.3(3) . . . . ?
C10A C5A C6A C7A -1.2(4) . . . . ?
C3A C5A C6A C7A -178.2(3) . . . . ?
N1A C6A C7A C8A -177.3(3) . . . . ?
C5A C6A C7A C8A 0.8(4) . . . . ?
C6A C7A C8A C9A 0.4(4) . . . . ?
C6A C7A C8A Cl1A 179.5(2) . . . . ?
C7A C8A C9A C10A -1.2(4) . . . . ?
Cl1A C8A C9A C10A 179.7(2) . . . . ?
C8A C9A C10A C5A 0.8(4) . . . . ?
C6A C5A C10A C9A 0.4(4) . . . . ?
C3A C5A C10A C9A 176.4(3) . . . . ?
C1A N2A C11A O1A 7.3(4) . . . . ?
C1A N2A C11A C12A -171.3(3) . . . . ?
C21A O1A C11A N2A -169.7(3) . . . . ?
C21A O1A C11A C12A 9.0(3) . . . . ?
N4A N3A C12A C11A 56.2(3) . . . . ?
C20A N3A C12A C11A -178.9(2) . . . . ?
N4A N3A C12A C13A -71.8(3) . . . . ?
C20A N3A C12A C13A 53.1(3) . . . . ?
N2A C11A C12A N3A 137.9(3) . . . . ?
O1A C11A C12A N3A -40.8(3) . . . . ?
N2A C11A C12A C13A -95.6(3) . . . . ?
O1A C11A C12A C13A 85.7(3) . . . . ?
N3A C12A C13A C14A 160.1(2) . . . . ?
C11A C12A C13A C14A 37.1(3) . . . . ?
N3A C12A C13A C18A -25.8(3) . . . . ?
C11A C12A C13A C18A -148.8(2) . . . . ?
C18A C13A C14A C15A -0.7(4) . . . . ?
C12A C13A C14A C15A 173.4(3) . . . . ?
C13A C14A C15A C16A 0.1(5) . . . . ?
C14A C15A C16A C17A 0.7(5) . . . . ?
C15A C16A C17A C18A -0.9(5) . . . . ?
C16A C17A C18A C13A 0.3(4) . . . . ?
C16A C17A C18A C19A 179.2(3) . . . . ?
C14A C13A C18A C17A 0.5(4) . . . . ?
C12A C13A C18A C17A -173.7(2) . . . . ?
C14A C13A C18A C19A -178.3(3) . . . . ?
C12A C13A C18A C19A 7.5(4) . . . . ?
C17A C18A C19A C20A 165.7(3) . . . . ?
C13A C18A C19A C20A -15.5(4) . . . . ?
N4A N3A C20A C19A 64.8(3) . . . . ?
C12A N3A C20A C19A -62.5(3) . . . . ?
C18A C19A C20A N3A 42.4(3) . . . . ?
N3A N4A C21A O1A 1.6(4) . . . . ?
N3A N4A C21A C22A -176.2(2) . . . . ?
C11A O1A C21A N4A 13.6(4) . . . . ?
C11A O1A C21A C22A -168.5(2) . . . . ?
N4A C21A C22A C23A -163.4(3) . . . . ?
O1A C21A C22A C23A 18.6(4) . . . . ?
N4A C21A C22A C27A 15.2(4) . . . . ?
O1A C21A C22A C27A -162.8(3) . . . . ?
C27A C22A C23A C24A -2.2(4) . . . . ?
C21A C22A C23A C24A 176.4(3) . . . . ?
C22A C23A C24A C25A 2.5(4) . . . . ?
C23A C24A C25A C26A -1.0(4) . . . . ?
C23A C24A C25A Cl2A 178.3(2) . . . . ?
C24A C25A C26A C27A -0.7(5) . . . . ?
Cl2A C25A C26A C27A -180.0(2) . . . . ?
C25A C26A C27A C22A 1.0(5) . . . . ?
C23A C22A C27A C26A 0.5(4) . . . . ?
C21A C22A C27A C26A -178.1(3) . . . . ?
C21B N3B N4B C20B -164.9(2) . . . . ?
C21B N3B N4B C12B -39.6(3) . . . . ?
C11B N2B C1B C2B -129.6(3) . . . . ?
N2B C1B C2B C3B 71.8(3) . . . . ?
C1B C2B C3B C4B -119.7(3) . . . . ?
C1B C2B C3B C5B 66.2(4) . . . . ?
C5B C3B C4B N1B -0.7(3) . . . . ?
C2B C3B C4B N1B -175.9(3) . . . . ?
C6B N1B C4B C3B 1.4(4) . . . . ?
C4B C3B C5B C10B -176.5(3) . . . . ?
C2B C3B C5B C10B -1.2(5) . . . . ?
C4B C3B C5B C6B -0.2(3) . . . . ?
C2B C3B C5B C6B 175.1(3) . . . . ?
C4B N1B C6B C7B 176.8(3) . . . . ?
C4B N1B C6B C5B -1.4(3) . . . . ?
C10B C5B C6B N1B 177.9(2) . . . . ?
C3B C5B C6B N1B 0.9(3) . . . . ?
C10B C5B C6B C7B -0.5(4) . . . . ?
C3B C5B C6B C7B -177.5(3) . . . . ?
N1B C6B C7B C8B -177.0(3) . . . . ?
C5B C6B C7B C8B 1.0(4) . . . . ?
C6B C7B C8B C9B -0.6(4) . . . . ?
C6B C7B C8B Cl1B 178.3(2) . . . . ?
C7B C8B C9B C10B -0.3(4) . . . . ?
Cl1B C8B C9B C10B -179.2(2) . . . . ?
C8B C9B C10B C5B 0.7(4) . . . . ?
C6B C5B C10B C9B -0.4(4) . . . . ?
C3B C5B C10B C9B 175.7(3) . . . . ?
C1B N2B C11B O1B 6.8(4) . . . . ?
C1B N2B C11B C12B -172.6(2) . . . . ?
C21B O1B C11B N2B -172.6(2) . . . . ?
C21B O1B C11B C12B 6.8(3) . . . . ?
N3B N4B C12B C11B 56.3(3) . . . . ?
C20B N4B C12B C11B -178.9(2) . . . . ?
N3B N4B C12B C13B -71.2(3) . . . . ?
C20B N4B C12B C13B 53.6(3) . . . . ?
N2B C11B C12B N4B 140.3(3) . . . . ?
O1B C11B C12B N4B -39.2(3) . . . . ?
N2B C11B C12B C13B -93.5(3) . . . . ?
O1B C11B C12B C13B 87.0(3) . . . . ?
N4B C12B C13B C14B 159.3(2) . . . . ?
C11B C12B C13B C14B 36.4(3) . . . . ?
N4B C12B C13B C18B -26.5(3) . . . . ?
C11B C12B C13B C18B -149.4(2) . . . . ?
C18B C13B C14B C15B -0.7(4) . . . . ?
C12B C13B C14B C15B 173.5(3) . . . . ?
C13B C14B C15B C16B 0.0(5) . . . . ?
C14B C15B C16B C17B 0.8(5) . . . . ?
C15B C16B C17B C18B -1.0(5) . . . . ?
C16B C17B C18B C13B 0.3(4) . . . . ?
C16B C17B C18B C19B 178.6(3) . . . . ?
C14B C13B C18B C17B 0.5(4) . . . . ?
C12B C13B C18B C17B -173.8(2) . . . . ?
C14B C13B C18B C19B -177.7(3) . . . . ?
C12B C13B C18B C19B 8.0(4) . . . . ?
C17B C18B C19B C20B 166.0(2) . . . . ?
C13B C18B C19B C20B -15.8(4) . . . . ?
N3B N4B C20B C19B 64.3(3) . . . . ?
C12B N4B C20B C19B -62.9(3) . . . . ?
C18B C19B C20B N4B 42.6(3) . . . . ?
N4B N3B C21B O1B 2.1(4) . . . . ?
N4B N3B C21B C22B -176.3(2) . . . . ?
C11B O1B C21B N3B 14.7(4) . . . . ?
C11B O1B C21B C22B -166.7(2) . . . . ?
N3B C21B C22B C23B -170.0(3) . . . . ?
O1B C21B C22B C23B 11.4(4) . . . . ?
N3B C21B C22B C27B 8.8(4) . . . . ?
O1B C21B C22B C27B -169.8(2) . . . . ?
C27B C22B C23B C24B -1.3(4) . . . . ?
C21B C22B C23B C24B 177.5(3) . . . . ?
C22B C23B C24B C25B 0.9(4) . . . . ?
C23B C24B C25B C26B -0.3(5) . . . . ?
C23B C24B C25B Cl2B -179.5(2) . . . . ?
C24B C25B C26B C27B 0.0(5) . . . . ?
Cl2B C25B C26B C27B 179.2(2) . . . . ?
C25B C26B C27B C22B -0.4(5) . . . . ?
C23B C22B C27B C26B 1.0(4) . . . . ?
C21B C22B C27B C26B -177.8(3) . . . . ?
