#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/45/1554504.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_1554504
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_sum            'C68 H68 Cl6 N4 O10 P2'
_chemical_formula_weight         1375.90
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2018-10-04 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   25.2081(12)
_cell_length_b                   25.2081(12)
_cell_length_c                   30.1100(16)
_cell_measurement_reflns_used    9796
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      66.65
_cell_measurement_theta_min      2.50
_cell_volume                     16570.0(14)
_computing_cell_refinement       'APEX3 v2018.1-0 (Bruker AXS)'
_computing_data_collection       'APEX3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT--(Sheldrick 2015)'
_diffrn_ambient_temperature      101(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            45452
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         2.500
_exptl_absorpt_coefficient_mu    2.992
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             6444
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.122
_refine_diff_density_max         1.136
_refine_diff_density_min         -0.981
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     480
_refine_ls_number_reflns         6508
_refine_ls_number_restraints     248
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0656
_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)+(0.1217P)²+95.1428P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1913
_refine_ls_wR_factor_ref         0.1949
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6020
_reflns_number_total             6508
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8qo01122b2.cif
_cod_data_source_block           i568
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_crystal_density_meas' value 'Not Measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        16570.0(18)
_cod_database_code               1554504
_shelx_shelxl_version_number     2017/1
_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. 
;
_computing_bruker_data_scaling   'SADABS V2018/1 (Bruker AXS Inc.)'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
P1 P 0.09373(3) 0.33269(3) 0.46406(2) 0.01778(18) Uani 1 1 d . . . . .
O4 O 0.12172(11) 0.19341(11) 0.29653(7) 0.0359(5) Uani 1 1 d . . . . .
O5 O 0.10840(13) 0.19677(17) 0.36650(8) 0.0573(8) Uani 1 1 d . . . . .
N1 N 0.31686(10) 0.35802(10) 0.34390(7) 0.0186(5) Uani 1 1 d . . . . .
N2 N 0.14251(12) 0.20114(13) 0.33516(9) 0.0322(6) Uani 1 1 d . . . . .
O1 O 0.30454(9) 0.34920(10) 0.41891(6) 0.0260(4) Uani 1 1 d . . . . .
O2 O 0.32803(8) 0.36967(9) 0.26894(6) 0.0215(4) Uani 1 1 d . . . . .
O3 O 0.19743(10) 0.21769(11) 0.34198(8) 0.0356(5) Uani 1 1 d . . . . .
C1 C 0.29490(12) 0.35727(12) 0.30144(8) 0.0179(5) Uani 1 1 d . . . . .
C2 C 0.28316(12) 0.34933(13) 0.38277(9) 0.0204(5) Uani 1 1 d . . . . .
C3 C 0.19667(12) 0.33839(12) 0.33494(8) 0.0174(5) Uani 1 1 d . . . . .
C4 C 0.22168(12) 0.34241(12) 0.37747(8) 0.0180(5) Uani 1 1 d . . . . .
C5 C 0.18933(12) 0.34009(12) 0.41481(8) 0.0195(5) Uani 1 1 d . . . . .
H5 H 0.207458 0.344290 0.443205 0.023 Uiso 1 1 calc R U . . .
C6 C 0.12978(12) 0.33161(12) 0.41190(8) 0.0180(5) Uani 1 1 d . . . . .
C7 C 0.10285(12) 0.32403(12) 0.37011(8) 0.0177(5) Uani 1 1 d . . . . .
C8 C 0.38086(12) 0.37214(13) 0.34900(9) 0.0217(6) Uani 1 1 d D . . . .
H8A H 0.3981(14) 0.3992(13) 0.3749(7) 0.026 Uiso 1 1 d D U . . .
H8B H 0.4044(13) 0.4016(12) 0.3256(8) 0.026 Uiso 1 1 d D U . . .
C9 C 0.3853(2) 0.3141(2) 0.3602(2) 0.0292(10) Uani 0.662(5) 1 d D U P A 1
H9 H 0.362244 0.296039 0.388325 0.035 Uiso 0.662(5) 1 calc R U P A 1
C10 C 0.3566(2) 0.2657(2) 0.32372(17) 0.0339(11) Uani 0.662(5) 1 d D U P A 1
H10A H 0.316191 0.260517 0.315821 0.041 Uiso 0.662(5) 1 calc R U P A 1
H10B H 0.382889 0.280520 0.296948 0.041 Uiso 0.662(5) 1 calc R U P A 1
C11 C 0.3483(4) 0.2035(3) 0.3369(3) 0.0441(18) Uani 0.662(5) 1 d D U P A 1
H11A H 0.329278 0.174579 0.312351 0.066 Uiso 0.662(5) 1 calc R U P A 1
H11B H 0.321899 0.188218 0.363202 0.066 Uiso 0.662(5) 1 calc R U P A 1
H11C H 0.388293 0.207903 0.343718 0.066 Uiso 0.662(5) 1 calc R U P A 1
C12 C 0.4530(2) 0.3338(3) 0.3683(2) 0.0361(11) Uani 0.662(5) 1 d D U P A 1
H12A H 0.456452 0.296505 0.370692 0.043 Uiso 0.662(5) 1 calc R U P A 1
H12B H 0.476958 0.356958 0.342024 0.043 Uiso 0.662(5) 1 calc R U P A 1
C13 C 0.4817(3) 0.3725(3) 0.4090(2) 0.0426(14) Uani 0.662(5) 1 d D U P A 1
H13A H 0.455597 0.351594 0.435050 0.051 Uiso 0.662(5) 1 calc R U P A 1
H13B H 0.482880 0.412111 0.405258 0.051 Uiso 0.662(5) 1 calc R U P A 1
C14 C 0.5460(3) 0.3850(4) 0.4182(3) 0.0567(16) Uani 0.662(5) 1 d D U P A 1
H14A H 0.545314 0.345435 0.420141 0.068 Uiso 0.662(5) 1 calc R U P A 1
H14B H 0.572769 0.408242 0.393010 0.068 Uiso 0.662(5) 1 calc R U P A 1
C15 C 0.5731(4) 0.4206(4) 0.4606(3) 0.071(2) Uani 0.662(5) 1 d D U P A 1
H15A H 0.602542 0.409930 0.472862 0.107 Uiso 0.662(5) 1 calc R U P A 1
H15B H 0.540257 0.410334 0.482243 0.107 Uiso 0.662(5) 1 calc R U P A 1
H15C H 0.593896 0.464589 0.454228 0.107 Uiso 0.662(5) 1 calc R U P A 1
C9X C 0.3927(4) 0.3209(4) 0.3361(4) 0.0259(17) Uani 0.338(5) 1 d D U P A 2
H9X H 0.382331 0.311350 0.303930 0.031 Uiso 0.338(5) 1 calc R U P A 2
C10X C 0.3522(4) 0.2632(4) 0.3629(3) 0.0268(17) Uani 0.338(5) 1 d D U P A 2
H10C H 0.308790 0.251638 0.358591 0.032 Uiso 0.338(5) 1 calc R U P A 2
H10D H 0.361850 0.272205 0.394873 0.032 Uiso 0.338(5) 1 calc R U P A 2
C11X C 0.3602(8) 0.2088(6) 0.3501(5) 0.039(3) Uani 0.338(5) 1 d D U P A 2
H11D H 0.362416 0.206855 0.317672 0.058 Uiso 0.338(5) 1 calc R U P A 2
H11E H 0.325192 0.170769 0.361060 0.058 Uiso 0.338(5) 1 calc R U P A 2
H11F H 0.398015 0.213968 0.363265 0.058 Uiso 0.338(5) 1 calc R U P A 2
C12X C 0.4614(4) 0.3443(5) 0.3419(4) 0.038(2) Uani 0.338(5) 1 d D U P A 2
H12C H 0.469890 0.312022 0.331667 0.045 Uiso 0.338(5) 1 calc R U P A 2
H12D H 0.484281 0.380258 0.322246 0.045 Uiso 0.338(5) 1 calc R U P A 2
C13X C 0.4862(6) 0.3627(8) 0.3889(5) 0.055(3) Uani 0.338(5) 1 d D U P A 2
H13C H 0.462593 0.327510 0.409044 0.066 Uiso 0.338(5) 1 calc R U P A 2
H13D H 0.479831 0.396585 0.398886 0.066 Uiso 0.338(5) 1 calc R U P A 2
C14X C 0.5542(6) 0.3831(9) 0.3928(6) 0.076(3) Uani 0.338(5) 1 d D U P A 2
H14C H 0.576005 0.408807 0.366819 0.091 Uiso 0.338(5) 1 calc R U P A 2
H14D H 0.558897 0.346438 0.392019 0.091 Uiso 0.338(5) 1 calc R U P A 2
C15X C 0.5844(9) 0.4195(10) 0.4354(7) 0.088(4) Uani 0.338(5) 1 d D U P A 2
H15D H 0.627999 0.432047 0.435368 0.133 Uiso 0.338(5) 1 calc R U P A 2
H15E H 0.564547 0.393635 0.461389 0.133 Uiso 0.338(5) 1 calc R U P A 2
H15F H 0.579882 0.455860 0.436590 0.133 Uiso 0.338(5) 1 calc R U P A 2
C16 C 0.04119(13) 0.25621(13) 0.48202(9) 0.0220(6) Uani 1 1 d . . . . .
C17 C 0.02107(13) 0.20679(14) 0.45328(10) 0.0269(6) Uani 1 1 d . . . . .
H17 H 0.033393 0.213241 0.423018 0.032 Uiso 1 1 calc R U . . .
C18 C -0.01703(15) 0.14807(15) 0.46896(12) 0.0356(7) Uani 1 1 d . . . . .
H18 H -0.031742 0.114138 0.449295 0.043 Uiso 1 1 calc R U . . .
C19 C -0.03370(16) 0.13881(17) 0.51334(14) 0.0434(9) Uani 1 1 d . . . . .
H19 H -0.059227 0.098307 0.524007 0.052 Uiso 1 1 calc R U . . .
C20 C -0.01370(17) 0.18773(18) 0.54239(12) 0.0422(9) Uani 1 1 d . . . . .
H20 H -0.025635 0.180834 0.572719 0.051 Uiso 1 1 calc R U . . .
C21 C 0.02384(15) 0.24683(16) 0.52691(10) 0.0320(7) Uani 1 1 d . . . . .
H21 H 0.037720 0.280714 0.546539 0.038 Uiso 1 1 calc R U . . .
C22 C 0.15563(13) 0.36499(14) 0.50400(9) 0.0234(6) Uani 1 1 d . . . . .
C23 C 0.17320(16) 0.32746(16) 0.52604(9) 0.0309(7) Uani 1 1 d . . . . .
H23 H 0.149405 0.284222 0.522972 0.037 Uiso 1 1 calc R U . . .
C24 C 0.22503(18) 0.3530(2) 0.55227(11) 0.0422(9) Uani 1 1 d . . . . .
H24 H 0.237058 0.327264 0.566840 0.051 Uiso 1 1 calc R U . . .
C25 C 0.25920(18) 0.4151(2) 0.55745(13) 0.0492(10) Uani 1 1 d . . . . .
H25 H 0.295051 0.432388 0.575330 0.059 Uiso 1 1 calc R U . . .
C26 C 0.24167(18) 0.4526(2) 0.53677(15) 0.0517(10) Uani 1 1 d . . . . .
H26 H 0.265112 0.495698 0.540877 0.062 Uiso 1 1 calc R U . . .
C27 C 0.19001(15) 0.42791(16) 0.50999(12) 0.0366(7) Uani 1 1 d . . . . .
H27 H 0.178187 0.454033 0.495761 0.044 Uiso 1 1 calc R U . . .
C28 C 0.06298(13) 0.38323(13) 0.46143(8) 0.0207(5) Uani 1 1 d . . . . .
C29 C 0.01168(14) 0.37077(14) 0.48649(9) 0.0256(6) Uani 1 1 d . . . . .
H29 H -0.007296 0.335536 0.504965 0.031 Uiso 1 1 calc R U . . .
C30 C -0.01139(16) 0.41021(16) 0.48421(11) 0.0350(7) Uani 1 1 d . . . . .
H30 H -0.046406 0.402082 0.501221 0.042 Uiso 1 1 calc R U . . .
C31 C 0.01637(18) 0.46161(17) 0.45719(12) 0.0404(8) Uani 1 1 d . . . . .
H31 H -0.000037 0.488244 0.455392 0.048 Uiso 1 1 calc R U . . .
C32 C 0.06817(17) 0.47423(15) 0.43271(11) 0.0364(7) Uani 1 1 d . . . . .
H32 H 0.087414 0.509870 0.414651 0.044 Uiso 1 1 calc R U . . .
C33 C 0.09179(14) 0.43533(14) 0.43449(10) 0.0279(6) Uani 1 1 d . . . . .
H33 H 0.127061 0.443790 0.417681 0.033 Uiso 1 1 calc R U . . .
C1S C 0.35218(19) 0.53751(18) 0.36731(17) 0.0551(11) Uani 1 1 d . . . . .
H1S H 0.309730 0.526953 0.358580 0.066 Uiso 1 1 calc R U . . .
Cl1 Cl 0.38628(6) 0.51876(6) 0.32318(5) 0.0776(4) Uani 1 1 d . . . . .
Cl2 Cl 0.34864(6) 0.49481(5) 0.41513(5) 0.0769(4) Uani 1 1 d . . . . .
Cl3 Cl 0.39546(6) 0.61606(5) 0.37823(5) 0.0735(4) 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 0.0181 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'
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
C16 P1 C28 115.34(13) . .
C16 P1 C22 106.92(13) . .
C28 P1 C22 106.94(13) . .
C16 P1 C6 110.50(13) . .
C28 P1 C6 111.61(12) . .
C22 P1 C6 104.81(12) . .
C1 N1 C2 124.2(2) . .
C1 N1 C8 118.6(2) . .
C2 N1 C8 117.1(2) . .
O5 N2 O3 120.5(3) . .
O5 N2 O4 118.3(3) . .
O3 N2 O4 120.9(3) . .
O2 C1 N1 121.1(2) . .
O2 C1 C7 120.6(2) . 16
N1 C1 C7 118.3(2) . 16
O1 C2 N1 121.0(2) . .
O1 C2 C4 122.4(2) . .
N1 C2 C4 116.6(2) . .
C3 C3 C7 120.9(3) 16 16
C3 C3 C4 118.5(3) 16 .
C7 C3 C4 120.6(2) 16 .
C5 C4 C3 120.4(2) . .
C5 C4 C2 118.8(2) . .
C3 C4 C2 120.8(2) . .
C4 C5 C6 121.4(2) . .
C4 C5 H5 119.3 . .
C6 C5 H5 119.3 . .
C7 C6 C5 119.0(2) . .
C7 C6 P1 124.5(2) . .
C5 C6 P1 116.45(19) . .
C6 C7 C3 119.7(2) . 16
C6 C7 C1 121.4(2) . 16
C3 C7 C1 118.9(2) 16 16
N1 C8 C9X 115.2(4) . .
N1 C8 C9 112.3(3) . .
N1 C8 H8A 107(2) . .
C9X C8 H8A 126(2) . .
C9 C8 H8A 105(2) . .
N1 C8 H8B 106(2) . .
C9X C8 H8B 99(2) . .
C9 C8 H8B 124(2) . .
H8A C8 H8B 99(3) . .
C10 C9 C12 112.3(4) . .
C10 C9 C8 111.5(4) . .
C12 C9 C8 108.6(4) . .
C10 C9 H9 108.1 . .
C12 C9 H9 108.1 . .
C8 C9 H9 108.1 . .
C11 C10 C9 113.6(5) . .
C11 C10 H10A 108.9 . .
C9 C10 H10A 108.9 . .
C11 C10 H10B 108.9 . .
C9 C10 H10B 108.9 . .
H10A C10 H10B 107.7 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C13 C12 C9 115.8(5) . .
C13 C12 H12A 108.3 . .
C9 C12 H12A 108.3 . .
C13 C12 H12B 108.3 . .
C9 C12 H12B 108.3 . .
H12A C12 H12B 107.4 . .
C12 C13 C14 113.7(6) . .
C12 C13 H13A 108.8 . .
C14 C13 H13A 108.8 . .
C12 C13 H13B 108.8 . .
C14 C13 H13B 108.8 . .
H13A C13 H13B 107.7 . .
C15 C14 C13 113.3(6) . .
C15 C14 H14A 108.9 . .
C13 C14 H14A 108.9 . .
C15 C14 H14B 108.9 . .
C13 C14 H14B 108.9 . .
H14A C14 H14B 107.7 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C8 C9X C10X 110.7(7) . .
C8 C9X C12X 107.9(7) . .
C10X C9X C12X 113.3(7) . .
C8 C9X H9X 108.3 . .
C10X C9X H9X 108.3 . .
C12X C9X H9X 108.3 . .
C9X C10X C11X 113.2(9) . .
C9X C10X H10C 108.9 . .
C11X C10X H10C 108.9 . .
C9X C10X H10D 108.9 . .
C11X C10X H10D 108.9 . .
H10C C10X H10D 107.8 . .
C10X C11X H11D 109.5 . .
C10X C11X H11E 109.5 . .
H11D C11X H11E 109.5 . .
C10X C11X H11F 109.5 . .
H11D C11X H11F 109.5 . .
H11E C11X H11F 109.5 . .
C13X C12X C9X 115.9(10) . .
C13X C12X H12C 108.3 . .
C9X C12X H12C 108.3 . .
C13X C12X H12D 108.3 . .
C9X C12X H12D 108.3 . .
H12C C12X H12D 107.4 . .
C12X C13X C14X 113.2(12) . .
C12X C13X H13C 108.9 . .
C14X C13X H13C 108.9 . .
C12X C13X H13D 108.9 . .
C14X C13X H13D 108.9 . .
H13C C13X H13D 107.7 . .
C13X C14X C15X 113.8(14) . .
C13X C14X H14C 108.8 . .
C15X C14X H14C 108.8 . .
C13X C14X H14D 108.8 . .
C15X C14X H14D 108.8 . .
H14C C14X H14D 107.7 . .
C14X C15X H15D 109.5 . .
C14X C15X H15E 109.5 . .
H15D C15X H15E 109.5 . .
C14X C15X H15F 109.5 . .
H15D C15X H15F 109.5 . .
H15E C15X H15F 109.5 . .
C17 C16 C21 120.4(3) . .
C17 C16 P1 121.3(2) . .
C21 C16 P1 118.2(2) . .
C18 C17 C16 119.6(3) . .
C18 C17 H17 120.2 . .
C16 C17 H17 120.2 . .
C17 C18 C19 120.0(3) . .
C17 C18 H18 120.0 . .
C19 C18 H18 120.0 . .
C20 C19 C18 121.0(3) . .
C20 C19 H19 119.5 . .
C18 C19 H19 119.5 . .
C19 C20 C21 119.6(3) . .
C19 C20 H20 120.2 . .
C21 C20 H20 120.2 . .
C20 C21 C16 119.5(3) . .
C20 C21 H21 120.2 . .
C16 C21 H21 120.2 . .
C27 C22 C23 119.0(3) . .
C27 C22 P1 120.4(2) . .
C23 C22 P1 120.3(2) . .
C24 C23 C22 120.2(3) . .
C24 C23 H23 119.9 . .
C22 C23 H23 119.9 . .
C25 C24 C23 120.5(3) . .
C25 C24 H24 119.8 . .
C23 C24 H24 119.8 . .
C24 C25 C26 120.0(3) . .
C24 C25 H25 120.0 . .
C26 C25 H25 120.0 . .
C25 C26 C27 120.4(4) . .
C25 C26 H26 119.8 . .
C27 C26 H26 119.8 . .
C26 C27 C22 119.9(3) . .
C26 C27 H27 120.0 . .
C22 C27 H27 120.0 . .
C29 C28 C33 121.0(3) . .
C29 C28 P1 119.9(2) . .
C33 C28 P1 119.1(2) . .
C30 C29 C28 119.3(3) . .
C30 C29 H29 120.4 . .
C28 C29 H29 120.4 . .
C29 C30 C31 120.3(3) . .
C29 C30 H30 119.9 . .
C31 C30 H30 119.9 . .
C30 C31 C32 120.1(3) . .
C30 C31 H31 119.9 . .
C32 C31 H31 119.9 . .
C33 C32 C31 120.4(3) . .
C33 C32 H32 119.8 . .
C31 C32 H32 119.8 . .
C32 C33 C28 118.9(3) . .
C32 C33 H33 120.5 . .
C28 C33 H33 120.5 . .
Cl3 C1S Cl1 109.4(2) . .
Cl3 C1S Cl2 110.4(3) . .
Cl1 C1S Cl2 109.3(2) . .
Cl3 C1S H1S 109.2 . .
Cl1 C1S H1S 109.2 . .
Cl2 C1S H1S 109.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C16 1.792(3) .
P1 C28 1.794(3) .
P1 C22 1.809(3) .
P1 C6 1.822(3) .
O4 N2 1.250(3) .
O5 N2 1.244(4) .
N1 C1 1.390(3) .
N1 C2 1.398(3) .
N1 C8 1.476(3) .
N2 O3 1.247(4) .
O1 C2 1.215(3) .
O2 C1 1.221(3) .
C1 C7 1.482(4) 16
C2 C4 1.479(4) .
C3 C3 1.406(5) 16
C3 C7 1.408(4) 16
C3 C4 1.409(4) .
C4 C5 1.373(4) .
C5 C6 1.409(4) .
C5 H5 0.9500 .
C6 C7 1.397(4) .
C8 C9X 1.516(9) .
C8 C9 1.560(5) .
C8 H8A 0.983(10) .
C8 H8B 0.979(10) .
C9 C10 1.527(7) .
C9 C12 1.539(6) .
C9 H9 1.0000 .
C10 C11 1.525(8) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 C13 1.507(7) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.514(7) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.513(9) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C9X C10X 1.527(10) .
C9X C12X 1.533(10) .
C9X H9X 1.0000 .
C10X C11X 1.531(12) .
C10X H10C 0.9900 .
C10X H10D 0.9900 .
C11X H11D 0.9800 .
C11X H11E 0.9800 .
C11X H11F 0.9800 .
C12X C13X 1.524(12) .
C12X H12C 0.9900 .
C12X H12D 0.9900 .
C13X C14X 1.528(13) .
C13X H13C 0.9900 .
C13X H13D 0.9900 .
C14X C15X 1.537(14) .
C14X H14C 0.9900 .
C14X H14D 0.9900 .
C15X H15D 0.9800 .
C15X H15E 0.9800 .
C15X H15F 0.9800 .
C16 C17 1.388(4) .
C16 C21 1.404(4) .
C17 C18 1.384(4) .
C17 H17 0.9500 .
C18 C19 1.385(5) .
C18 H18 0.9500 .
C19 C20 1.385(6) .
C19 H19 0.9500 .
C20 C21 1.386(5) .
C20 H20 0.9500 .
C21 H21 0.9500 .
C22 C27 1.387(5) .
C22 C23 1.397(4) .
C23 C24 1.380(5) .
C23 H23 0.9500 .
C24 C25 1.367(6) .
C24 H24 0.9500 .
C25 C26 1.376(6) .
C25 H25 0.9500 .
C26 C27 1.387(5) .
C26 H26 0.9500 .
C27 H27 0.9500 .
C28 C29 1.391(4) .
C28 C33 1.399(4) .
C29 C30 1.382(4) .
C29 H29 0.9500 .
C30 C31 1.387(5) .
C30 H30 0.9500 .
C31 C32 1.391(5) .
C31 H31 0.9500 .
C32 C33 1.379(4) .
C32 H32 0.9500 .
C33 H33 0.9500 .
C1S Cl3 1.749(4) .
C1S Cl1 1.770(5) .
C1S Cl2 1.773(5) .
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
C2 N1 C1 O2 174.5(2) . .
C8 N1 C1 O2 -2.0(4) . .
C2 N1 C1 C7 -3.9(4) . 16
C8 N1 C1 C7 179.6(2) . 16
C1 N1 C2 O1 178.4(3) . .
C8 N1 C2 O1 -5.0(4) . .
C1 N1 C2 C4 -3.5(4) . .
C8 N1 C2 C4 173.1(2) . .
C3 C3 C4 C5 -3.8(5) 16 .
C7 C3 C4 C5 178.0(2) 16 .
C3 C3 C4 C2 176.4(3) 16 .
C7 C3 C4 C2 -1.8(4) 16 .
O1 C2 C4 C5 4.7(4) . .
N1 C2 C4 C5 -173.4(2) . .
O1 C2 C4 C3 -175.4(3) . .
N1 C2 C4 C3 6.5(4) . .
C3 C4 C5 C6 2.2(4) . .
C2 C4 C5 C6 -178.0(2) . .
C4 C5 C6 C7 1.5(4) . .
C4 C5 C6 P1 -177.5(2) . .
C16 P1 C6 C7 81.0(3) . .
C28 P1 C6 C7 -48.8(3) . .
C22 P1 C6 C7 -164.2(2) . .
C16 P1 C6 C5 -100.1(2) . .
C28 P1 C6 C5 130.2(2) . .
C22 P1 C6 C5 14.8(2) . .
C5 C6 C7 C3 -3.4(4) . 16
P1 C6 C7 C3 175.5(2) . 16
C5 C6 C7 C1 174.4(2) . 16
P1 C6 C7 C1 -6.6(4) . 16
C1 N1 C8 C9X -75.1(5) . .
C2 N1 C8 C9X 108.2(5) . .
C1 N1 C8 C9 -105.6(3) . .
C2 N1 C8 C9 77.6(4) . .
N1 C8 C9 C10 60.0(5) . .
N1 C8 C9 C12 -175.8(4) . .
C12 C9 C10 C11 69.3(7) . .
C8 C9 C10 C11 -168.5(5) . .
C10 C9 C12 C13 -169.3(5) . .
C8 C9 C12 C13 66.9(6) . .
C9 C12 C13 C14 173.8(6) . .
C12 C13 C14 C15 -176.5(6) . .
N1 C8 C9X C10X -57.5(8) . .
N1 C8 C9X C12X 178.0(6) . .
C8 C9X C10X C11X 177.7(8) . .
C12X C9X C10X C11X -61.0(12) . .
C8 C9X C12X C13X 61.7(12) . .
C10X C9X C12X C13X -61.2(13) . .
C9X C12X C13X C14X 177.6(12) . .
C12X C13X C14X C15X 162.6(15) . .
C28 P1 C16 C17 112.4(2) . .
C22 P1 C16 C17 -128.9(2) . .
C6 P1 C16 C17 -15.4(3) . .
C28 P1 C16 C21 -71.8(3) . .
C22 P1 C16 C21 46.9(3) . .
C6 P1 C16 C21 160.5(2) . .
C21 C16 C17 C18 0.9(4) . .
P1 C16 C17 C18 176.7(2) . .
C16 C17 C18 C19 -1.5(4) . .
C17 C18 C19 C20 1.2(5) . .
C18 C19 C20 C21 -0.4(5) . .
C19 C20 C21 C16 -0.2(5) . .
C17 C16 C21 C20 -0.1(4) . .
P1 C16 C21 C20 -176.0(2) . .
C16 P1 C22 C27 -154.8(2) . .
C28 P1 C22 C27 -30.8(3) . .
C6 P1 C22 C27 87.8(3) . .
C16 P1 C22 C23 31.4(3) . .
C28 P1 C22 C23 155.4(2) . .
C6 P1 C22 C23 -86.0(2) . .
C27 C22 C23 C24 -1.9(4) . .
P1 C22 C23 C24 172.0(2) . .
C22 C23 C24 C25 0.9(5) . .
C23 C24 C25 C26 0.6(6) . .
C24 C25 C26 C27 -1.1(6) . .
C25 C26 C27 C22 0.1(6) . .
C23 C22 C27 C26 1.4(5) . .
P1 C22 C27 C26 -172.5(3) . .
C16 P1 C28 C29 22.4(3) . .
C22 P1 C28 C29 -96.3(2) . .
C6 P1 C28 C29 149.6(2) . .
C16 P1 C28 C33 -158.5(2) . .
C22 P1 C28 C33 82.8(3) . .
C6 P1 C28 C33 -31.3(3) . .
C33 C28 C29 C30 0.8(5) . .
P1 C28 C29 C30 179.8(2) . .
C28 C29 C30 C31 0.0(5) . .
C29 C30 C31 C32 -0.9(6) . .
C30 C31 C32 C33 1.1(6) . .
C31 C32 C33 C28 -0.3(5) . .
C29 C28 C33 C32 -0.6(5) . .
P1 C28 C33 C32 -179.7(3) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168304502
