#------------------------------------------------------------------------------
#$Date: 2020-07-06 06:47:19 +0300 (Mon, 06 Jul 2020) $
#$Revision: 253982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/75/7157537.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_7157537
loop_
_publ_author_name
'Jiang, Shuai-Shuai'
'Xiao, Yu-Ting'
'Wu, Yan-Chen'
'Luo, Shu-Zheng'
'Song, Ren-Jie'
'Li, Jin-Heng'
_publ_section_title
;
 Manganese(iii)-promoted tandem phosphinoylation/cyclization of
 2-arylindoles/2-arylbenzimidazoles with disubstituted phosphine oxides.
;
_journal_issue                   25
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4843
_journal_page_last               4847
_journal_paper_doi               10.1039/d0ob00877j
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         C33H37Cl3NO2P
_chemical_formula_sum            'C33 H37 Cl3 N O2 P'
_chemical_formula_weight         616.95
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-03-02 deposited with the CCDC.	2020-06-08 downloaded from the CCDC.
;
_cell_angle_alpha                109.078(3)
_cell_angle_beta                 94.549(3)
_cell_angle_gamma                91.826(3)
_cell_formula_units_Z            2
_cell_length_a                   10.546(3)
_cell_length_b                   12.611(3)
_cell_length_c                   12.642(3)
_cell_measurement_reflns_used    4517
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.45
_cell_measurement_theta_min      2.37
_cell_volume                     1581.0(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12286
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.463
_exptl_absorpt_coefficient_mu    0.371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.6596
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.740
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         5854
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0540
_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)+(0.0701P)²+0.9594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1524
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4594
_reflns_number_total             5854
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00877j2.cif
_cod_data_source_block           A
_cod_depositor_comments          'Adding full bibliography for 7157537.cif.'
_cod_database_code               7157537
_shelx_shelxl_version_number     2014/7
_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   0.936
_shelx_estimated_absorpt_t_max   0.946
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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
C1 C 0.4156(3) 0.3202(2) -0.2500(3) 0.0597(7) Uani 1 1 d . . . . .
H1 H 0.4512 0.3060 -0.3179 0.072 Uiso 1 1 calc R U . . .
C2 C 0.2862(3) 0.3301(3) -0.2443(3) 0.0688(9) Uani 1 1 d . . . . .
H2 H 0.2341 0.3231 -0.3094 0.083 Uiso 1 1 calc R U . . .
C3 C 0.2324(3) 0.3501(2) -0.1442(3) 0.0679(9) Uani 1 1 d . . . . .
H3 H 0.1447 0.3556 -0.1437 0.082 Uiso 1 1 calc R U . . .
C4 C 0.3048(2) 0.3623(2) -0.0449(3) 0.0573(7) Uani 1 1 d . . . . .
H4 H 0.2682 0.3760 0.0225 0.069 Uiso 1 1 calc R U . . .
C5 C 0.4348(2) 0.35295(19) -0.0502(2) 0.0451(6) Uani 1 1 d . . . . .
C6 C 0.4917(2) 0.3323(2) -0.1501(2) 0.0466(6) Uani 1 1 d . . . . .
C7 C 0.6270(2) 0.3237(2) -0.1266(2) 0.0449(6) Uani 1 1 d . . . . .
C8 C 0.6489(2) 0.34053(19) -0.0148(2) 0.0403(5) Uani 1 1 d . . . . .
C9 C 0.7181(3) 0.2992(2) -0.2134(2) 0.0488(6) Uani 1 1 d . . . . .
C10 C 0.7944(3) 0.2087(2) -0.2303(3) 0.0616(7) Uani 1 1 d . . . . .
H10 H 0.7886 0.1628 -0.1862 0.074 Uiso 1 1 calc R U . . .
C11 C 0.8788(3) 0.1861(3) -0.3114(3) 0.0772(9) Uani 1 1 d . . . . .
H11 H 0.9309 0.1262 -0.3207 0.093 Uiso 1 1 calc R U . . .
C12 C 0.8858(4) 0.2519(3) -0.3785(3) 0.0805(10) Uani 1 1 d . . . . .
H12 H 0.9422 0.2360 -0.4339 0.097 Uiso 1 1 calc R U . . .
C13 C 0.8108(3) 0.3403(3) -0.3644(3) 0.0732(9) Uani 1 1 d . . . . .
H13 H 0.8158 0.3845 -0.4103 0.088 Uiso 1 1 calc R U . . .
C14 C 0.7266(3) 0.3648(2) -0.2818(2) 0.0580(7) Uani 1 1 d . . . . .
H14 H 0.6758 0.4256 -0.2724 0.070 Uiso 1 1 calc R U . . .
C15 C 0.7645(2) 0.36019(19) 0.0622(2) 0.0416(5) Uani 1 1 d . . . . .
C16 C 0.8824(2) 0.3840(2) 0.0288(2) 0.0523(6) Uani 1 1 d . . . . .
H16 H 0.8888 0.3803 -0.0452 0.063 Uiso 1 1 calc R U . . .
C17 C 0.9888(3) 0.4126(3) 0.1044(3) 0.0626(8) Uani 1 1 d . . . . .
H17 H 1.0669 0.4276 0.0812 0.075 Uiso 1 1 calc R U . . .
C18 C 0.9805(3) 0.4193(2) 0.2142(3) 0.0630(8) Uani 1 1 d . . . . .
H18 H 1.0527 0.4396 0.2654 0.076 Uiso 1 1 calc R U . . .
C19 C 0.8654(3) 0.3959(2) 0.2484(2) 0.0541(7) Uani 1 1 d . . . . .
H19 H 0.8604 0.4005 0.3229 0.065 Uiso 1 1 calc R U . . .
C20 C 0.7562(2) 0.36518(19) 0.1729(2) 0.0417(5) Uani 1 1 d . . . . .
C21 C 0.6293(2) 0.33698(19) 0.2110(2) 0.0410(5) Uani 1 1 d . . . . .
C22 C 0.5165(2) 0.3667(2) 0.1442(2) 0.0449(6) Uani 1 1 d . . . . .
C23 C 0.6181(3) 0.3990(2) 0.3358(2) 0.0571(7) Uani 1 1 d . . . . .
H23A H 0.6772 0.3709 0.3805 0.086 Uiso 1 1 calc R U . . .
H23B H 0.5329 0.3869 0.3530 0.086 Uiso 1 1 calc R U . . .
H23C H 0.6371 0.4780 0.3521 0.086 Uiso 1 1 calc R U . . .
C24 C 0.6027(2) 0.20679(18) 0.1813(2) 0.0385(5) Uani 1 1 d . . . . .
H24A H 0.6015 0.1732 0.1004 0.046 Uiso 1 1 calc R U . . .
H24B H 0.5175 0.1946 0.2005 0.046 Uiso 1 1 calc R U . . .
C25 C 0.7743(2) 0.0219(2) 0.1241(2) 0.0511(6) Uani 1 1 d . . . . .
C26 C 0.8438(3) 0.0887(3) 0.0624(3) 0.0733(9) Uani 1 1 d . . . . .
H26A H 0.8876 0.0384 0.0044 0.110 Uiso 1 1 calc R U . . .
H26B H 0.9044 0.1429 0.1146 0.110 Uiso 1 1 calc R U . . .
H26C H 0.7832 0.1268 0.0294 0.110 Uiso 1 1 calc R U . . .
C27 C 0.6741(3) -0.0600(3) 0.0413(3) 0.0781(10) Uani 1 1 d . . . . .
H27A H 0.6090 -0.0187 0.0180 0.117 Uiso 1 1 calc R U . . .
H27B H 0.6369 -0.1083 0.0770 0.117 Uiso 1 1 calc R U . . .
H27C H 0.7135 -0.1045 -0.0232 0.117 Uiso 1 1 calc R U . . .
C28 C 0.8728(3) -0.0447(3) 0.1674(3) 0.0820(10) Uani 1 1 d . . . . .
H28A H 0.8303 -0.0940 0.1991 0.123 Uiso 1 1 calc R U . . .
H28B H 0.9322 0.0064 0.2240 0.123 Uiso 1 1 calc R U . . .
H28C H 0.9177 -0.0883 0.1062 0.123 Uiso 1 1 calc R U . . .
C29 C 0.6059(3) 0.0637(2) 0.3237(2) 0.0545(7) Uani 1 1 d . . . . .
C30 C 0.4909(3) -0.0100(3) 0.2532(3) 0.0776(10) Uani 1 1 d . . . . .
H30A H 0.5197 -0.0777 0.2024 0.116 Uiso 1 1 calc R U . . .
H30B H 0.4455 0.0302 0.2110 0.116 Uiso 1 1 calc R U . . .
H30C H 0.4354 -0.0288 0.3019 0.116 Uiso 1 1 calc R U . . .
C31 C 0.6872(4) -0.0043(3) 0.3813(3) 0.0874(11) Uani 1 1 d . . . . .
H31A H 0.7639 0.0395 0.4185 0.131 Uiso 1 1 calc R U . . .
H31B H 0.7087 -0.0723 0.3259 0.131 Uiso 1 1 calc R U . . .
H31C H 0.6400 -0.0226 0.4356 0.131 Uiso 1 1 calc R U . . .
C32 C 0.5571(3) 0.1613(3) 0.4158(3) 0.0719(9) Uani 1 1 d . . . . .
H32A H 0.5133 0.1327 0.4654 0.108 Uiso 1 1 calc R U . . .
H32B H 0.4997 0.2014 0.3823 0.108 Uiso 1 1 calc R U . . .
H32C H 0.6278 0.2112 0.4576 0.108 Uiso 1 1 calc R U . . .
C33 C 0.1155(3) 0.2338(3) 0.3686(3) 0.0687(8) Uani 1 1 d . . . . .
H33 H 0.0250 0.2200 0.3411 0.082 Uiso 1 1 calc R U . . .
Cl1 Cl 0.20168(13) 0.22411(18) 0.25576(13) 0.1630(8) Uani 1 1 d . . . . .
Cl2 Cl 0.15733(11) 0.13233(9) 0.42878(11) 0.1051(4) Uani 1 1 d . . . . .
Cl3 Cl 0.13643(16) 0.36623(9) 0.46955(10) 0.1282(5) Uani 1 1 d . . . . .
N1 N 0.53208(18) 0.35676(16) 0.03392(17) 0.0419(5) Uani 1 1 d . . . . .
O1 O 0.41473(18) 0.38804(18) 0.18144(18) 0.0661(6) Uani 1 1 d . . . . .
O2 O 0.81728(16) 0.19617(14) 0.32386(15) 0.0501(4) Uani 1 1 d . . . . .
P1 P 0.71022(6) 0.12692(5) 0.24556(5) 0.04012(18) Uani 1 1 d . . . . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 117.9(3) . . ?
C2 C1 H1 121.0 . . ?
C6 C1 H1 121.0 . . ?
C3 C2 C1 121.5(3) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C4 C3 C2 121.9(3) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 116.8(3) . . ?
C3 C4 H4 121.6 . . ?
C5 C4 H4 121.6 . . ?
C4 C5 C6 122.6(3) . . ?
C4 C5 N1 130.4(3) . . ?
C6 C5 N1 106.9(2) . . ?
C5 C6 C1 119.3(2) . . ?
C5 C6 C7 108.3(2) . . ?
C1 C6 C7 132.3(3) . . ?
C8 C7 C6 107.2(2) . . ?
C8 C7 C9 129.1(2) . . ?
C6 C7 C9 123.7(2) . . ?
C7 C8 N1 109.1(2) . . ?
C7 C8 C15 133.4(2) . . ?
N1 C8 C15 116.8(2) . . ?
C14 C9 C10 118.5(3) . . ?
C14 C9 C7 120.5(2) . . ?
C10 C9 C7 121.1(2) . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C9 C14 C13 120.2(3) . . ?
C9 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C20 C15 C16 119.3(2) . . ?
C20 C15 C8 119.8(2) . . ?
C16 C15 C8 120.7(2) . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 120.3(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C19 119.9(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C20 120.9(3) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C15 C20 C19 119.1(2) . . ?
C15 C20 C21 120.4(2) . . ?
C19 C20 C21 120.6(2) . . ?
C20 C21 C23 112.8(2) . . ?
C20 C21 C22 111.42(19) . . ?
C23 C21 C22 107.5(2) . . ?
C20 C21 C24 111.82(19) . . ?
C23 C21 C24 111.13(19) . . ?
C22 C21 C24 101.62(18) . . ?
O1 C22 N1 120.8(2) . . ?
O1 C22 C21 122.4(2) . . ?
N1 C22 C21 116.5(2) . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 P1 119.85(16) . . ?
C21 C24 H24A 107.4 . . ?
P1 C24 H24A 107.4 . . ?
C21 C24 H24B 107.4 . . ?
P1 C24 H24B 107.4 . . ?
H24A C24 H24B 106.9 . . ?
C27 C25 C26 108.9(3) . . ?
C27 C25 C28 109.1(3) . . ?
C26 C25 C28 107.7(3) . . ?
C27 C25 P1 114.9(2) . . ?
C26 C25 P1 106.48(18) . . ?
C28 C25 P1 109.4(2) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C32 C29 C30 108.4(3) . . ?
C32 C29 C31 107.7(3) . . ?
C30 C29 C31 109.8(3) . . ?
C32 C29 P1 106.64(18) . . ?
C30 C29 P1 115.3(2) . . ?
C31 C29 P1 108.7(2) . . ?
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 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
Cl1 C33 Cl3 111.8(2) . . ?
Cl1 C33 Cl2 110.69(19) . . ?
Cl3 C33 Cl2 109.83(18) . . ?
Cl1 C33 H33 108.1 . . ?
Cl3 C33 H33 108.1 . . ?
Cl2 C33 H33 108.1 . . ?
C22 N1 C5 126.4(2) . . ?
C22 N1 C8 125.0(2) . . ?
C5 N1 C8 108.5(2) . . ?
O2 P1 C24 114.51(10) . . ?
O2 P1 C29 109.61(12) . . ?
C24 P1 C29 104.66(12) . . ?
O2 P1 C25 109.72(11) . . ?
C24 P1 C25 104.53(12) . . ?
C29 P1 C25 113.78(13) . . ?
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 1.379(4) . ?
C1 C6 1.403(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.379(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(4) . ?
C5 N1 1.406(3) . ?
C6 C7 1.449(4) . ?
C7 C8 1.358(3) . ?
C7 C9 1.479(4) . ?
C8 N1 1.412(3) . ?
C8 C15 1.459(3) . ?
C9 C14 1.385(4) . ?
C9 C10 1.385(4) . ?
C10 C11 1.376(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.361(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.388(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.391(4) . ?
C15 C16 1.399(3) . ?
C16 C17 1.371(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.376(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.393(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.527(3) . ?
C21 C23 1.531(4) . ?
C21 C22 1.532(3) . ?
C21 C24 1.570(3) . ?
C22 O1 1.209(3) . ?
C22 N1 1.382(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 P1 1.849(2) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C27 1.525(4) . ?
C25 C26 1.529(4) . ?
C25 C28 1.534(4) . ?
C25 P1 1.860(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C32 1.527(4) . ?
C29 C30 1.531(4) . ?
C29 C31 1.536(4) . ?
C29 P1 1.859(3) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 Cl1 1.725(3) . ?
C33 Cl3 1.733(4) . ?
C33 Cl2 1.740(4) . ?
C33 H33 0.9800 . ?
O2 P1 1.4873(17) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C33 H33 O2 0.98 2.19 3.144(4) 165.7 1_455
C4 H4 O1 0.93 2.40 2.911(4) 114.8 .
C33 H33 O2 0.98 2.19 3.144(4) 165.7 1_455
C4 H4 O1 0.93 2.40 2.911(4) 114.8 .
C4 H4 O1 0.93 2.40 2.911(4) 114.8 .
C33 H33 O2 0.98 2.19 3.144(4) 165.7 1_455
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
C6 C1 C2 C3 -0.6(4) . . . . ?
C1 C2 C3 C4 0.6(5) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C3 C4 C5 N1 -177.3(2) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
N1 C5 C6 C1 177.8(2) . . . . ?
C4 C5 C6 C7 -178.0(2) . . . . ?
N1 C5 C6 C7 -0.2(3) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
C2 C1 C6 C7 177.8(3) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C1 C6 C7 C8 -178.5(3) . . . . ?
C5 C6 C7 C9 178.4(2) . . . . ?
C1 C6 C7 C9 0.8(4) . . . . ?
C6 C7 C8 N1 1.5(3) . . . . ?
C9 C7 C8 N1 -177.7(2) . . . . ?
C6 C7 C8 C15 -168.4(2) . . . . ?
C9 C7 C8 C15 12.5(4) . . . . ?
C8 C7 C9 C14 -126.5(3) . . . . ?
C6 C7 C9 C14 54.5(4) . . . . ?
C8 C7 C9 C10 55.2(4) . . . . ?
C6 C7 C9 C10 -123.8(3) . . . . ?
C14 C9 C10 C11 1.4(4) . . . . ?
C7 C9 C10 C11 179.8(3) . . . . ?
C9 C10 C11 C12 -1.5(5) . . . . ?
C10 C11 C12 C13 0.7(5) . . . . ?
C11 C12 C13 C14 0.1(5) . . . . ?
C10 C9 C14 C13 -0.5(4) . . . . ?
C7 C9 C14 C13 -178.9(3) . . . . ?
C12 C13 C14 C9 -0.2(5) . . . . ?
C7 C8 C15 C20 -174.5(2) . . . . ?
N1 C8 C15 C20 16.2(3) . . . . ?
C7 C8 C15 C16 11.2(4) . . . . ?
N1 C8 C15 C16 -158.1(2) . . . . ?
C20 C15 C16 C17 -0.4(4) . . . . ?
C8 C15 C16 C17 173.9(2) . . . . ?
C15 C16 C17 C18 -0.6(4) . . . . ?
C16 C17 C18 C19 0.8(5) . . . . ?
C17 C18 C19 C20 0.0(4) . . . . ?
C16 C15 C20 C19 1.2(3) . . . . ?
C8 C15 C20 C19 -173.2(2) . . . . ?
C16 C15 C20 C21 -178.6(2) . . . . ?
C8 C15 C20 C21 7.0(3) . . . . ?
C18 C19 C20 C15 -1.0(4) . . . . ?
C18 C19 C20 C21 178.8(2) . . . . ?
C15 C20 C21 C23 -151.5(2) . . . . ?
C19 C20 C21 C23 28.7(3) . . . . ?
C15 C20 C21 C22 -30.5(3) . . . . ?
C19 C20 C21 C22 149.7(2) . . . . ?
C15 C20 C21 C24 82.4(3) . . . . ?
C19 C20 C21 C24 -97.4(3) . . . . ?
C20 C21 C22 O1 -154.4(2) . . . . ?
C23 C21 C22 O1 -30.4(3) . . . . ?
C24 C21 C22 O1 86.4(3) . . . . ?
C20 C21 C22 N1 32.1(3) . . . . ?
C23 C21 C22 N1 156.1(2) . . . . ?
C24 C21 C22 N1 -87.1(2) . . . . ?
C20 C21 C24 P1 63.2(2) . . . . ?
C23 C21 C24 P1 -63.8(3) . . . . ?
C22 C21 C24 P1 -177.84(16) . . . . ?
O1 C22 N1 C5 -9.9(4) . . . . ?
C21 C22 N1 C5 163.8(2) . . . . ?
O1 C22 N1 C8 175.0(2) . . . . ?
C21 C22 N1 C8 -11.4(3) . . . . ?
C4 C5 N1 C22 2.9(4) . . . . ?
C6 C5 N1 C22 -174.6(2) . . . . ?
C4 C5 N1 C8 178.7(2) . . . . ?
C6 C5 N1 C8 1.2(2) . . . . ?
C7 C8 N1 C22 174.2(2) . . . . ?
C15 C8 N1 C22 -14.0(3) . . . . ?
C7 C8 N1 C5 -1.7(3) . . . . ?
C15 C8 N1 C5 170.08(19) . . . . ?
C21 C24 P1 O2 0.3(2) . . . . ?
C21 C24 P1 C29 120.32(19) . . . . ?
C21 C24 P1 C25 -119.79(19) . . . . ?
C32 C29 P1 O2 59.5(2) . . . . ?
C30 C29 P1 O2 179.9(2) . . . . ?
C31 C29 P1 O2 -56.3(3) . . . . ?
C32 C29 P1 C24 -63.8(2) . . . . ?
C30 C29 P1 C24 56.6(3) . . . . ?
C31 C29 P1 C24 -179.6(2) . . . . ?
C32 C29 P1 C25 -177.25(19) . . . . ?
C30 C29 P1 C25 -56.9(3) . . . . ?
C31 C29 P1 C25 66.9(3) . . . . ?
C27 C25 P1 O2 176.0(2) . . . . ?
C26 C25 P1 O2 -63.3(2) . . . . ?
C28 C25 P1 O2 52.8(2) . . . . ?
C27 C25 P1 C24 -60.8(2) . . . . ?
C26 C25 P1 C24 59.9(2) . . . . ?
C28 C25 P1 C24 176.1(2) . . . . ?
C27 C25 P1 C29 52.8(3) . . . . ?
C26 C25 P1 C29 173.5(2) . . . . ?
C28 C25 P1 C29 -70.4(2) . . . . ?
