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#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/45/1554506.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_1554506
loop_
_publ_author_name
'Ng, Chee Koon'
'Tam, Teck Lip Dexter'
'Wei, Fengxia'
'Lu, Xuefeng'
'Wu, Jishan'
_publ_section_title
;
 Anion--π and anion--π-radical interactions in
 bis(triphenylphosphonium)-naphthalene diimide salts
;
_journal_issue                   1
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              110
_journal_paper_doi               10.1039/C8QO01122B
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C34 H34 Br Cl3 N O2 P'
_chemical_formula_sum            'C34 H34 Br Cl3 N O2 P'
_chemical_formula_weight         705.85
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-10-04 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.084(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9670(6)
_cell_length_b                   15.8648(10)
_cell_length_c                   20.3172(11)
_cell_measurement_reflns_used    3273
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.436
_cell_measurement_theta_min      3.583
_cell_volume                     3413.2(3)
_computing_cell_refinement
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_collection       'APEX3 v2016.9.0'
_computing_data_reduction        'Saint, APEX v2014.11.0.'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX3 v2016.9.0'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT, Acta Cryst., Sect. A 2015, A71, 3-8.'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from θ/2θ scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24969
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.436
_diffrn_reflns_theta_min         3.583
_exptl_absorpt_coefficient_mu    4.484
_exptl_absorpt_correction_T_max  0.573
_exptl_absorpt_correction_T_min  0.486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       'prism frag'
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.140
_refine_diff_density_max         1.233
_refine_diff_density_min         -0.643
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         6662
_refine_ls_number_restraints     220
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0630
_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)+(0.0771P)²+13.2757P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.1801
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5263
_reflns_number_total             6662
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8qo01122b2.cif
_cod_data_source_block           h398
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1554506
_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   0.486
_shelx_estimated_absorpt_t_max   0.573
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Br1 Br 0.22821(5) 0.35501(4) 0.48590(3) 0.04283(18) Uani 1 1 d . . . . .
P1 P 0.47974(10) 0.62564(6) 0.68629(5) 0.0241(2) Uani 1 1 d . . . . .
N1 N 0.4468(3) 0.7182(2) 0.47072(16) 0.0232(7) Uani 1 1 d . . . . .
O1 O 0.4868(3) 0.73772(17) 0.58546(14) 0.0291(6) Uani 1 1 d . . . . .
O2 O 0.4283(3) 0.69664(17) 0.35792(14) 0.0297(6) Uani 1 1 d . . . . .
C1 C 0.4752(4) 0.6890(2) 0.5377(2) 0.0239(8) Uani 1 1 d . . . . .
C2 C 0.4875(4) 0.5972(2) 0.54941(19) 0.0231(8) Uani 1 1 d . . . . .
C3 C 0.4991(4) 0.5634(2) 0.61406(19) 0.0224(8) Uani 1 1 d . . . . .
C4 C 0.5180(4) 0.4757(2) 0.62400(19) 0.0241(8) Uani 1 1 d . . . . .
H4 H 0.5254 0.4524 0.6680 0.029 Uiso 1 1 calc R U . . .
C5 C 0.5259(4) 0.4236(2) 0.5715(2) 0.0237(8) Uani 1 1 d . . . . .
C6 C 0.5091(4) 0.4564(2) 0.50514(19) 0.0225(8) Uani 1 1 d . . . . .
C7 C 0.4491(4) 0.6674(3) 0.41508(19) 0.0246(8) Uani 1 1 d . . . . .
C8A C 0.4330(8) 0.8094(6) 0.4616(9) 0.0303(11) Uani 0.668(5) 1 d D U P A 1
H8A1 H 0.4366 0.8240 0.4147 0.036 Uiso 0.668(5) 1 calc R U P A 1
H8A2 H 0.5049 0.8376 0.4937 0.036 Uiso 0.668(5) 1 calc R U P A 1
C9A C 0.3102(5) 0.8430(4) 0.4732(3) 0.0338(10) Uani 0.668(5) 1 d D U P A 1
H9A H 0.3057 0.8247 0.5196 0.041 Uiso 0.668(5) 1 calc R U P A 1
C12A C 0.3156(7) 0.9404(4) 0.4726(4) 0.0389(12) Uani 0.668(5) 1 d D U P A 1
H12A H 0.3939 0.9588 0.5060 0.047 Uiso 0.668(5) 1 calc R U P A 1
H12B H 0.3210 0.9591 0.4270 0.047 Uiso 0.668(5) 1 calc R U P A 1
C13A C 0.2048(9) 0.9840(5) 0.4891(4) 0.0481(13) Uani 0.668(5) 1 d D U P A 1
H13A H 0.1866 0.9563 0.5291 0.058 Uiso 0.668(5) 1 calc R U P A 1
H13B H 0.1295 0.9771 0.4501 0.058 Uiso 0.668(5) 1 calc R U P A 1
C14A C 0.2282(9) 1.0820(5) 0.5048(5) 0.0544(14) Uani 0.668(5) 1 d D U P A 1
H14A H 0.3066 1.0895 0.5417 0.065 Uiso 0.668(5) 1 calc R U P A 1
H14B H 0.2393 1.1110 0.4636 0.065 Uiso 0.668(5) 1 calc R U P A 1
C15A C 0.1192(9) 1.1210(5) 0.5260(5) 0.0609(17) Uani 0.668(5) 1 d D U P A 1
H15A H 0.0404 1.1088 0.4915 0.091 Uiso 0.668(5) 1 calc R U P A 1
H15B H 0.1313 1.1821 0.5303 0.091 Uiso 0.668(5) 1 calc R U P A 1
H15C H 0.1149 1.0974 0.5699 0.091 Uiso 0.668(5) 1 calc R U P A 1
C10A C 0.1951(7) 0.8078(5) 0.4216(3) 0.0396(12) Uani 0.668(5) 1 d D U P A 1
H10A H 0.1189 0.8238 0.4361 0.048 Uiso 0.668(5) 1 calc R U P A 1
H10B H 0.2007 0.7455 0.4229 0.048 Uiso 0.668(5) 1 calc R U P A 1
C11A C 0.1774(8) 0.8362(5) 0.3481(3) 0.0429(13) Uani 0.668(5) 1 d D U P A 1
H11A H 0.1656 0.8975 0.3453 0.064 Uiso 0.668(5) 1 calc R U P A 1
H11B H 0.1029 0.8085 0.3190 0.064 Uiso 0.668(5) 1 calc R U P A 1
H11C H 0.2522 0.8210 0.3329 0.064 Uiso 0.668(5) 1 calc R U P A 1
C8B C 0.4168(14) 0.8112(11) 0.4578(19) 0.0327(17) Uani 0.332(5) 1 d D U P A 2
H8B1 H 0.4658 0.8337 0.4271 0.039 Uiso 0.332(5) 1 calc R U P A 2
H8B2 H 0.4427 0.8423 0.5015 0.039 Uiso 0.332(5) 1 calc R U P A 2
C9B C 0.2767(12) 0.8254(6) 0.4258(6) 0.0375(13) Uani 0.332(5) 1 d D U P A 2
H9B H 0.2546 0.7974 0.3801 0.045 Uiso 0.332(5) 1 calc R U P A 2
C12B C 0.2547(15) 0.9213(6) 0.4142(5) 0.0408(13) Uani 0.332(5) 1 d D U P A 2
H12C H 0.3156 0.9428 0.3898 0.049 Uiso 0.332(5) 1 calc R U P A 2
H12D H 0.1688 0.9300 0.3843 0.049 Uiso 0.332(5) 1 calc R U P A 2
C13B C 0.2681(18) 0.9726(7) 0.4781(6) 0.0470(15) Uani 0.332(5) 1 d D U P A 2
H13C H 0.3588 0.9759 0.5026 0.056 Uiso 0.332(5) 1 calc R U P A 2
H13D H 0.2241 0.9430 0.5082 0.056 Uiso 0.332(5) 1 calc R U P A 2
C14B C 0.2133(19) 1.0659(8) 0.4650(7) 0.0536(17) Uani 0.332(5) 1 d D U P A 2
H14C H 0.2564 1.0962 0.4348 0.064 Uiso 0.332(5) 1 calc R U P A 2
H14D H 0.1220 1.0635 0.4418 0.064 Uiso 0.332(5) 1 calc R U P A 2
C15B C 0.2327(19) 1.1131(8) 0.5313(8) 0.0539(19) Uani 0.332(5) 1 d D U P A 2
H15D H 0.1766 1.0900 0.5573 0.081 Uiso 0.332(5) 1 calc R U P A 2
H15E H 0.2133 1.1729 0.5219 0.081 Uiso 0.332(5) 1 calc R U P A 2
H15F H 0.3207 1.1071 0.5578 0.081 Uiso 0.332(5) 1 calc R U P A 2
C10B C 0.1944(11) 0.7868(9) 0.4677(8) 0.044(4) Uani 0.332(5) 1 d D . P A 2
H10C H 0.2094 0.7252 0.4708 0.053 Uiso 0.332(5) 1 calc R U P A 2
H10D H 0.2208 0.8099 0.5145 0.053 Uiso 0.332(5) 1 calc R U P A 2
C11B C 0.0536(12) 0.8024(12) 0.4392(10) 0.061(5) Uani 0.332(5) 1 d D . P A 2
H11D H 0.0339 0.8607 0.4486 0.092 Uiso 0.332(5) 1 calc R U P A 2
H11E H 0.0060 0.7638 0.4608 0.092 Uiso 0.332(5) 1 calc R U P A 2
H11F H 0.0303 0.7928 0.3898 0.092 Uiso 0.332(5) 1 calc R U P A 2
C16 C 0.3306(4) 0.6801(3) 0.6617(2) 0.0294(9) Uani 1 1 d . . . . .
C17 C 0.2335(4) 0.6464(3) 0.6101(2) 0.0373(10) Uani 1 1 d . . . . .
H17 H 0.2466 0.5961 0.5875 0.045 Uiso 1 1 calc R U . . .
C18 C 0.1181(5) 0.6865(4) 0.5921(3) 0.0524(14) Uani 1 1 d . . . . .
H18 H 0.0521 0.6641 0.5564 0.063 Uiso 1 1 calc R U . . .
C19 C 0.0976(5) 0.7588(4) 0.6254(3) 0.0539(14) Uani 1 1 d . . . . .
H19 H 0.0177 0.7860 0.6127 0.065 Uiso 1 1 calc R U . . .
C20 C 0.1929(6) 0.7914(4) 0.6769(3) 0.0509(14) Uani 1 1 d . . . . .
H20 H 0.1778 0.8407 0.7000 0.061 Uiso 1 1 calc R U . . .
C21 C 0.3115(5) 0.7531(3) 0.6957(2) 0.0351(10) Uani 1 1 d . . . . .
H21 H 0.3776 0.7763 0.7310 0.042 Uiso 1 1 calc R U . . .
C22 C 0.6178(4) 0.6868(3) 0.7242(2) 0.0294(9) Uani 1 1 d . . . . .
C23 C 0.6279(4) 0.7224(3) 0.7886(2) 0.0338(10) Uani 1 1 d . . . . .
H23 H 0.5609 0.7168 0.8100 0.041 Uiso 1 1 calc R U . . .
C24 C 0.7366(5) 0.7657(3) 0.8208(3) 0.0442(12) Uani 1 1 d . . . . .
H24 H 0.7439 0.7908 0.8641 0.053 Uiso 1 1 calc R U . . .
C25 C 0.8346(5) 0.7725(4) 0.7899(3) 0.0506(13) Uani 1 1 d . . . . .
H25 H 0.9092 0.8020 0.8123 0.061 Uiso 1 1 calc R U . . .
C26 C 0.8252(5) 0.7368(3) 0.7267(3) 0.0429(11) Uani 1 1 d . . . . .
H26 H 0.8934 0.7417 0.7061 0.052 Uiso 1 1 calc R U . . .
C27 C 0.7158(4) 0.6934(3) 0.6928(2) 0.0337(10) Uani 1 1 d . . . . .
H27 H 0.7087 0.6690 0.6493 0.040 Uiso 1 1 calc R U . . .
C28 C 0.4657(5) 0.5492(3) 0.7498(2) 0.0310(10) Uani 1 1 d . . . . .
C29 C 0.3467(5) 0.5169(3) 0.7485(2) 0.0399(11) Uani 1 1 d . . . . .
H29 H 0.2732 0.5395 0.7180 0.048 Uiso 1 1 calc R U . . .
C30 C 0.3368(7) 0.4515(3) 0.7924(3) 0.0559(15) Uani 1 1 d . . . . .
H30 H 0.2559 0.4297 0.7920 0.067 Uiso 1 1 calc R U . . .
C31 C 0.4412(7) 0.4184(3) 0.8356(3) 0.0570(16) Uani 1 1 d . . . . .
H31 H 0.4329 0.3732 0.8648 0.068 Uiso 1 1 calc R U . . .
C32 C 0.5596(7) 0.4498(3) 0.8377(3) 0.0558(17) Uani 1 1 d . . . . .
H32 H 0.6323 0.4266 0.8685 0.067 Uiso 1 1 calc R U . . .
C33 C 0.5723(5) 0.5162(3) 0.7943(2) 0.0414(11) Uani 1 1 d . . . . .
H33 H 0.6534 0.5382 0.7955 0.050 Uiso 1 1 calc R U . . .
Cl1S Cl 0.16206(14) 0.59102(10) 0.34745(9) 0.0644(4) Uani 1 1 d . . . . .
Cl2S Cl -0.00771(15) 0.45532(11) 0.29272(8) 0.0634(4) Uani 1 1 d . . . . .
Cl3S Cl -0.04230(13) 0.55080(8) 0.40954(7) 0.0511(3) Uani 1 1 d . . . . .
C1S C 0.0670(6) 0.5091(4) 0.3680(3) 0.0524(13) Uani 1 1 d . . . . .
H1S H 0.1233 0.4686 0.3996 0.063 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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
C22 P1 C16 117.6(2) . .
C22 P1 C28 106.0(2) . .
C16 P1 C28 106.3(2) . .
C22 P1 C3 112.05(19) . .
C16 P1 C3 108.84(19) . .
C28 P1 C3 105.08(18) . .
C1 N1 C7 123.5(3) . .
C1 N1 C8A 116.3(7) . .
C7 N1 C8A 119.5(7) . .
C1 N1 C8B 118.3(14) . .
C7 N1 C8B 118.1(14) . .
O1 C1 N1 121.0(3) . .
O1 C1 C2 120.6(3) . .
N1 C1 C2 118.3(3) . .
C3 C2 C6 119.7(3) . 3_666
C3 C2 C1 120.9(3) . .
C6 C2 C1 119.3(3) 3_666 .
C2 C3 C4 119.2(3) . .
C2 C3 P1 123.3(3) . .
C4 C3 P1 117.4(3) . .
C5 C4 C3 121.3(4) . .
C5 C4 H4 119.4 . .
C3 C4 H4 119.4 . .
C4 C5 C6 120.2(4) . .
C4 C5 C7 119.4(3) . 3_666
C6 C5 C7 120.4(3) . 3_666
C2 C6 C6 120.7(4) 3_666 3_666
C2 C6 C5 120.5(3) 3_666 .
C6 C6 C5 118.8(4) 3_666 .
O2 C7 N1 121.0(4) . .
O2 C7 C5 121.9(4) . 3_666
N1 C7 C5 117.1(3) . 3_666
N1 C8A C9A 113.2(7) . .
N1 C8A H8A1 108.9 . .
C9A C8A H8A1 108.9 . .
N1 C8A H8A2 108.9 . .
C9A C8A H8A2 108.9 . .
H8A1 C8A H8A2 107.8 . .
C10A C9A C8A 112.0(8) . .
C10A C9A C12A 112.9(5) . .
C8A C9A C12A 108.1(5) . .
C10A C9A H9A 107.9 . .
C8A C9A H9A 107.9 . .
C12A C9A H9A 107.9 . .
C13A C12A C9A 115.0(5) . .
C13A C12A H12A 108.5 . .
C9A C12A H12A 108.5 . .
C13A C12A H12B 108.5 . .
C9A C12A H12B 108.5 . .
H12A C12A H12B 107.5 . .
C12A C13A C14A 113.2(7) . .
C12A C13A H13A 108.9 . .
C14A C13A H13A 108.9 . .
C12A C13A H13B 108.9 . .
C14A C13A H13B 108.9 . .
H13A C13A H13B 107.7 . .
C15A C14A C13A 111.1(7) . .
C15A C14A H14A 109.4 . .
C13A C14A H14A 109.4 . .
C15A C14A H14B 109.4 . .
C13A C14A H14B 109.4 . .
H14A C14A H14B 108.0 . .
C14A C15A H15A 109.5 . .
C14A C15A H15B 109.5 . .
H15A C15A H15B 109.5 . .
C14A C15A H15C 109.5 . .
H15A C15A H15C 109.5 . .
H15B C15A H15C 109.5 . .
C9A C10A C11A 116.0(6) . .
C9A C10A H10A 108.3 . .
C11A C10A H10A 108.3 . .
C9A C10A H10B 108.3 . .
C11A C10A H10B 108.3 . .
H10A C10A H10B 107.4 . .
C10A C11A H11A 109.5 . .
C10A C11A H11B 109.5 . .
H11A C11A H11B 109.5 . .
C10A C11A H11C 109.5 . .
H11A C11A H11C 109.5 . .
H11B C11A H11C 109.5 . .
N1 C8B C9B 111.6(12) . .
N1 C8B H8B1 109.3 . .
C9B C8B H8B1 109.3 . .
N1 C8B H8B2 109.3 . .
C9B C8B H8B2 109.3 . .
H8B1 C8B H8B2 108.0 . .
C10B C9B C8B 112.4(16) . .
C10B C9B C12B 112.9(10) . .
C8B C9B C12B 108.1(5) . .
C10B C9B H9B 107.7 . .
C8B C9B H9B 107.7 . .
C12B C9B H9B 107.7 . .
C13B C12B C9B 115.0(7) . .
C13B C12B H12C 108.5 . .
C9B C12B H12C 108.5 . .
C13B C12B H12D 108.5 . .
C9B C12B H12D 108.5 . .
H12C C12B H12D 107.5 . .
C12B C13B C14B 114.2(7) . .
C12B C13B H13C 108.7 . .
C14B C13B H13C 108.7 . .
C12B C13B H13D 108.7 . .
C14B C13B H13D 108.7 . .
H13C C13B H13D 107.6 . .
C15B C14B C13B 110.6(8) . .
C15B C14B H14C 109.5 . .
C13B C14B H14C 109.5 . .
C15B C14B H14D 109.5 . .
C13B C14B H14D 109.5 . .
H14C C14B H14D 108.1 . .
C14B C15B H15D 109.5 . .
C14B C15B H15E 109.5 . .
H15D C15B H15E 109.5 . .
C14B C15B H15F 109.5 . .
H15D C15B H15F 109.5 . .
H15E C15B H15F 109.5 . .
C11B C10B C9B 114.3(14) . .
C11B C10B H10C 108.7 . .
C9B C10B H10C 108.7 . .
C11B C10B H10D 108.7 . .
C9B C10B H10D 108.7 . .
H10C C10B H10D 107.6 . .
C10B C11B H11D 109.5 . .
C10B C11B H11E 109.5 . .
H11D C11B H11E 109.5 . .
C10B C11B H11F 109.5 . .
H11D C11B H11F 109.5 . .
H11E C11B H11F 109.5 . .
C17 C16 C21 120.6(4) . .
C17 C16 P1 119.1(3) . .
C21 C16 P1 120.3(4) . .
C18 C17 C16 119.5(5) . .
C18 C17 H17 120.2 . .
C16 C17 H17 120.2 . .
C17 C18 C19 120.6(5) . .
C17 C18 H18 119.7 . .
C19 C18 H18 119.7 . .
C20 C19 C18 119.9(5) . .
C20 C19 H19 120.1 . .
C18 C19 H19 120.1 . .
C19 C20 C21 121.1(5) . .
C19 C20 H20 119.5 . .
C21 C20 H20 119.5 . .
C16 C21 C20 118.4(5) . .
C16 C21 H21 120.8 . .
C20 C21 H21 120.8 . .
C27 C22 C23 121.0(4) . .
C27 C22 P1 120.7(3) . .
C23 C22 P1 118.1(3) . .
C24 C23 C22 119.3(4) . .
C24 C23 H23 120.4 . .
C22 C23 H23 120.4 . .
C25 C24 C23 120.1(4) . .
C25 C24 H24 120.0 . .
C23 C24 H24 120.0 . .
C26 C25 C24 120.7(5) . .
C26 C25 H25 119.7 . .
C24 C25 H25 119.7 . .
C25 C26 C27 120.4(5) . .
C25 C26 H26 119.8 . .
C27 C26 H26 119.8 . .
C22 C27 C26 118.6(4) . .
C22 C27 H27 120.7 . .
C26 C27 H27 120.7 . .
C33 C28 C29 120.1(4) . .
C33 C28 P1 120.4(4) . .
C29 C28 P1 119.1(3) . .
C30 C29 C28 119.4(5) . .
C30 C29 H29 120.3 . .
C28 C29 H29 120.3 . .
C31 C30 C29 120.7(6) . .
C31 C30 H30 119.7 . .
C29 C30 H30 119.7 . .
C30 C31 C32 120.7(5) . .
C30 C31 H31 119.7 . .
C32 C31 H31 119.7 . .
C31 C32 C33 119.8(5) . .
C31 C32 H32 120.1 . .
C33 C32 H32 120.1 . .
C28 C33 C32 119.4(6) . .
C28 C33 H33 120.3 . .
C32 C33 H33 120.3 . .
Cl2S C1S Cl3S 112.2(3) . .
Cl2S C1S Cl1S 108.6(3) . .
Cl3S C1S Cl1S 110.5(3) . .
Cl2S C1S H1S 108.5 . .
Cl3S C1S H1S 108.5 . .
Cl1S C1S H1S 108.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C22 1.794(5) .
P1 C16 1.801(4) .
P1 C28 1.806(4) .
P1 C3 1.826(4) .
N1 C1 1.393(5) .
N1 C7 1.394(5) .
N1 C8A 1.462(9) .
N1 C8B 1.519(16) .
O1 C1 1.222(5) .
O2 C7 1.216(5) .
C1 C2 1.475(5) .
C2 C3 1.393(5) .
C2 C6 1.405(5) 3_666
C3 C4 1.414(5) .
C4 C5 1.370(5) .
C4 H4 0.9500 .
C5 C6 1.412(5) .
C5 C7 1.481(5) 3_666
C6 C2 1.405(5) 3_666
C6 C6 1.407(8) 3_666
C7 C5 1.481(5) 3_666
C8A C9A 1.522(5) .
C8A H8A1 0.9900 .
C8A H8A2 0.9900 .
C9A C10A 1.522(5) .
C9A C12A 1.546(8) .
C9A H9A 1.0000 .
C12A C13A 1.510(9) .
C12A H12A 0.9900 .
C12A H12B 0.9900 .
C13A C14A 1.595(11) .
C13A H13A 0.9900 .
C13A H13B 0.9900 .
C14A C15A 1.505(11) .
C14A H14A 0.9900 .
C14A H14B 0.9900 .
C15A H15A 0.9800 .
C15A H15B 0.9800 .
C15A H15C 0.9800 .
C10A C11A 1.522(5) .
C10A H10A 0.9900 .
C10A H10B 0.9900 .
C11A H11A 0.9800 .
C11A H11B 0.9800 .
C11A H11C 0.9800 .
C8B C9B 1.522(6) .
C8B H8B1 0.9900 .
C8B H8B2 0.9900 .
C9B C10B 1.521(6) .
C9B C12B 1.547(9) .
C9B H9B 1.0000 .
C12B C13B 1.507(10) .
C12B H12C 0.9900 .
C12B H12D 0.9900 .
C13B C14B 1.594(11) .
C13B H13C 0.9900 .
C13B H13D 0.9900 .
C14B C15B 1.507(11) .
C14B H14C 0.9900 .
C14B H14D 0.9900 .
C15B H15D 0.9800 .
C15B H15E 0.9800 .
C15B H15F 0.9800 .
C10B C11B 1.521(6) .
C10B H10C 0.9900 .
C10B H10D 0.9900 .
C11B H11D 0.9800 .
C11B H11E 0.9800 .
C11B H11F 0.9800 .
C16 C17 1.392(7) .
C16 C21 1.393(6) .
C17 C18 1.378(7) .
C17 H17 0.9500 .
C18 C19 1.380(9) .
C18 H18 0.9500 .
C19 C20 1.373(9) .
C19 H19 0.9500 .
C20 C21 1.396(7) .
C20 H20 0.9500 .
C21 H21 0.9500 .
C22 C27 1.389(6) .
C22 C23 1.404(6) .
C23 C24 1.383(7) .
C23 H23 0.9500 .
C24 C25 1.383(8) .
C24 H24 0.9500 .
C25 C26 1.382(7) .
C25 H25 0.9500 .
C26 C27 1.399(7) .
C26 H26 0.9500 .
C27 H27 0.9500 .
C28 C33 1.381(7) .
C28 C29 1.395(7) .
C29 C30 1.391(7) .
C29 H29 0.9500 .
C30 C31 1.354(9) .
C30 H30 0.9500 .
C31 C32 1.381(10) .
C31 H31 0.9500 .
C32 C33 1.404(8) .
C32 H32 0.9500 .
C33 H33 0.9500 .
Cl1S C1S 1.783(6) .
Cl2S C1S 1.757(6) .
Cl3S C1S 1.764(6) .
C1S H1S 1.0000 .
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_4
C7 N1 C1 O1 171.1(4) . .
C8A N1 C1 O1 0.4(6) . .
C8B N1 C1 O1 -6.4(9) . .
C7 N1 C1 C2 -10.6(6) . .
C8A N1 C1 C2 178.7(5) . .
C8B N1 C1 C2 171.9(8) . .
O1 C1 C2 C3 6.9(6) . .
N1 C1 C2 C3 -171.5(4) . .
O1 C1 C2 C6 -171.4(4) . 3_666
N1 C1 C2 C6 10.3(6) . 3_666
C6 C2 C3 C4 1.9(6) 3_666 .
C1 C2 C3 C4 -176.3(4) . .
C6 C2 C3 P1 -173.5(3) 3_666 .
C1 C2 C3 P1 8.3(5) . .
C22 P1 C3 C2 -78.9(4) . .
C16 P1 C3 C2 52.9(4) . .
C28 P1 C3 C2 166.4(4) . .
C22 P1 C3 C4 105.7(3) . .
C16 P1 C3 C4 -122.5(3) . .
C28 P1 C3 C4 -9.0(4) . .
C2 C3 C4 C5 0.4(6) . .
P1 C3 C4 C5 176.1(3) . .
C3 C4 C5 C6 -3.1(6) . .
C3 C4 C5 C7 177.6(4) . 3_666
C4 C5 C6 C2 -177.7(4) . 3_666
C7 C5 C6 C2 1.7(6) 3_666 3_666
C4 C5 C6 C6 3.3(7) . 3_666
C7 C5 C6 C6 -177.3(5) 3_666 3_666
C1 N1 C7 O2 -177.1(4) . .
C8A N1 C7 O2 -6.7(7) . .
C8B N1 C7 O2 0.4(9) . .
C1 N1 C7 C5 4.6(6) . 3_666
C8A N1 C7 C5 175.0(5) . 3_666
C8B N1 C7 C5 -177.9(8) . 3_666
C1 N1 C8A C9A -74.0(11) . .
C7 N1 C8A C9A 114.9(11) . .
N1 C8A C9A C10A -63.3(12) . .
N1 C8A C9A C12A 171.7(8) . .
C10A C9A C12A C13A 60.3(8) . .
C8A C9A C12A C13A -175.3(9) . .
C9A C12A C13A C14A 166.7(7) . .
C12A C13A C14A C15A -175.7(8) . .
C8A C9A C10A C11A -67.5(9) . .
C12A C9A C10A C11A 54.8(8) . .
C1 N1 C8B C9B -107(2) . .
C7 N1 C8B C9B 76(2) . .
N1 C8B C9B C10B 55(3) . .
N1 C8B C9B C12B -179.8(16) . .
C10B C9B C12B C13B 54.0(18) . .
C8B C9B C12B C13B -71(2) . .
C9B C12B C13B C14B -165.8(14) . .
C12B C13B C14B C15B -179.0(16) . .
C8B C9B C10B C11B 177.7(15) . .
C12B C9B C10B C11B 55.1(17) . .
C22 P1 C16 C17 154.7(3) . .
C28 P1 C16 C17 -86.7(4) . .
C3 P1 C16 C17 26.0(4) . .
C22 P1 C16 C21 -27.8(4) . .
C28 P1 C16 C21 90.7(4) . .
C3 P1 C16 C21 -156.6(3) . .
C21 C16 C17 C18 1.0(7) . .
P1 C16 C17 C18 178.4(4) . .
C16 C17 C18 C19 -1.0(8) . .
C17 C18 C19 C20 0.1(9) . .
C18 C19 C20 C21 0.9(8) . .
C17 C16 C21 C20 0.0(7) . .
P1 C16 C21 C20 -177.4(4) . .
C19 C20 C21 C16 -0.9(8) . .
C16 P1 C22 C27 -117.7(4) . .
C28 P1 C22 C27 123.6(4) . .
C3 P1 C22 C27 9.5(4) . .
C16 P1 C22 C23 66.9(4) . .
C28 P1 C22 C23 -51.7(4) . .
C3 P1 C22 C23 -165.8(3) . .
C27 C22 C23 C24 1.0(7) . .
P1 C22 C23 C24 176.3(4) . .
C22 C23 C24 C25 -1.0(7) . .
C23 C24 C25 C26 0.4(8) . .
C24 C25 C26 C27 0.3(9) . .
C23 C22 C27 C26 -0.3(7) . .
P1 C22 C27 C26 -175.5(4) . .
C25 C26 C27 C22 -0.3(8) . .
C22 P1 C28 C33 -33.4(4) . .
C16 P1 C28 C33 -159.3(3) . .
C3 P1 C28 C33 85.4(4) . .
C22 P1 C28 C29 153.6(3) . .
C16 P1 C28 C29 27.7(4) . .
C3 P1 C28 C29 -87.6(4) . .
C33 C28 C29 C30 0.0(7) . .
P1 C28 C29 C30 173.0(4) . .
C28 C29 C30 C31 -0.6(8) . .
C29 C30 C31 C32 0.9(8) . .
C30 C31 C32 C33 -0.5(8) . .
C29 C28 C33 C32 0.4(6) . .
P1 C28 C33 C32 -172.6(3) . .
C31 C32 C33 C28 -0.2(7) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168304504
