#------------------------------------------------------------------------------
#$Date: 2019-11-24 08:26:35 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237297 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/45/1554508.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_1554508
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            'C66 H66 Cl N2 O7.33 P2'
_chemical_formula_weight         1101.93
_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   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                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   24.8062(9)
_cell_length_b                   24.8062(9)
_cell_length_c                   30.0418(11)
_cell_measurement_reflns_used    9763
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.20
_cell_measurement_theta_min      3.56
_cell_volume                     16009.5(10)
_computing_cell_refinement       'APEX3 v2016.1-0 (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      100(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0443
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            49333
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        66.594
_diffrn_reflns_theta_max         66.594
_diffrn_reflns_theta_min         2.528
_exptl_absorpt_coefficient_mu    1.268
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_crystal_colour            Dark_red
_exptl_crystal_density_diffrn    1.029
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             5235
_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.285
_exptl_crystal_size_min          0.217
_refine_diff_density_max         1.495
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.200
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         6201
_refine_ls_number_restraints     105
_refine_ls_restrained_S_all      2.018
_refine_ls_R_factor_all          0.1453
_refine_ls_R_factor_gt           0.1377
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4022
_refine_ls_wR_factor_ref         0.4169
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5456
_reflns_number_total             6201
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8qo01122b2.cif
_cod_data_source_block           I122
_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        16009.5(13)
_cod_database_code               1554508
_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. 
;
_computing_bruker_data_scaling   'SADABS V2012/1 (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 0.57570(4) 0.00179(5) 0.13022(3) 0.0463(4) Uani 1 1 d . . . . .
Cl1 Cl 0.3333 0.6667 0.22108(17) 0.0906(14) Uani 0.5 3 d S T P A 1
Cl2 Cl 0.4500(5) 0.5914(6) 0.3182(5) 0.108(3) Uani 0.1667 1 d . . P B 2
Cl3 Cl 0.1296(6) 0.4900(9) 0.0016(4) 0.118(4) Uani 0.1667 1 d . . P C 3
O1 O 0.39322(15) 0.04406(18) 0.08456(9) 0.0618(8) Uani 1 1 d . . . . .
O2 O 0.37820(12) 0.04203(13) -0.06654(8) 0.0501(7) Uani 1 1 d . . . . .
N1 N 0.38311(14) 0.03964(15) 0.00920(10) 0.0475(8) Uani 1 1 d . . . . .
C1 C 0.41111(18) 0.0353(2) 0.04876(12) 0.0492(9) Uani 1 1 d . . . . .
C2 C 0.40121(16) 0.03268(17) -0.03298(11) 0.0433(8) Uani 1 1 d . . . . .
C3 C 0.44761(16) 0.01350(17) -0.03718(11) 0.0440(8) Uani 1 1 d . . . . .
C4 C 0.47668(15) 0.00857(16) 0.00168(11) 0.0420(8) Uani 1 1 d . . . . .
C5 C 0.45971(16) 0.01990(17) 0.04376(11) 0.0458(8) Uani 1 1 d . . . . .
C6 C 0.33228(19) 0.0533(2) 0.01345(13) 0.0521(9) Uani 1 1 d . . . . .
H6A H 0.3267 0.0699 -0.0151 0.062 Uiso 1 1 calc R U . . .
H6B H 0.3429 0.0855 0.0366 0.062 Uiso 1 1 calc R U . . .
C7 C 0.2698(3) -0.0074(3) 0.0264(2) 0.0841(16) Uani 1 1 d . . . . .
H7 H 0.2770 -0.0221 0.0556 0.101 Uiso 1 1 calc R U . D 1
C8 C 0.2509(3) -0.0596(3) -0.0062(3) 0.096(2) Uani 1 1 d . . . . .
H8A H 0.2870 -0.0652 -0.0125 0.115 Uiso 1 1 calc R U . . .
H8B H 0.2380 -0.0490 -0.0345 0.115 Uiso 1 1 calc R U . . .
C9 C 0.1973(5) -0.1203(4) 0.0121(3) 0.135(4) Uani 1 1 d . . . . .
H9A H 0.1767 -0.1495 -0.0125 0.203 Uiso 1 1 calc R U . . .
H9B H 0.1672 -0.1117 0.0270 0.203 Uiso 1 1 calc R U . . .
H9C H 0.2135 -0.1385 0.0335 0.203 Uiso 1 1 calc R U . . .
C10 C 0.2185(4) 0.0081(4) 0.0336(4) 0.075(2) Uani 0.640(11) 1 d D U P E 1
H10A H 0.2143 0.0278 0.0062 0.090 Uiso 0.640(11) 1 calc R U P E 1
H10B H 0.1788 -0.0313 0.0379 0.090 Uiso 0.640(11) 1 calc R U P E 1
C11 C 0.2274(6) 0.0504(6) 0.0723(5) 0.090(2) Uani 0.640(11) 1 d D U P E 1
H11A H 0.2660 0.0907 0.0675 0.107 Uiso 0.640(11) 1 calc R U P E 1
H11B H 0.2329 0.0316 0.0997 0.107 Uiso 0.640(11) 1 calc R U P E 1
C12 C 0.1733(6) 0.0624(6) 0.0791(6) 0.105(3) Uani 0.640(11) 1 d D U P E 1
H12A H 0.1742 0.0905 0.0553 0.125 Uiso 0.640(11) 1 calc R U P E 1
H12B H 0.1335 0.0226 0.0765 0.125 Uiso 0.640(11) 1 calc R U P E 1
C13 C 0.1758(8) 0.0893(8) 0.1208(6) 0.126(4) Uani 0.640(11) 1 d D U P E 1
H13A H 0.1404 0.0963 0.1238 0.189 Uiso 0.640(11) 1 calc R U P E 1
H13B H 0.1741 0.0613 0.1445 0.189 Uiso 0.640(11) 1 calc R U P E 1
H13C H 0.2147 0.1292 0.1233 0.189 Uiso 0.640(11) 1 calc R U P E 1
C10X C 0.2233(8) 0.0279(9) 0.0111(7) 0.087(3) Uani 0.360(11) 1 d D U P E 2
H10C H 0.2471 0.0655 -0.0074 0.105 Uiso 0.360(11) 1 calc R U P E 2
H10D H 0.1845 -0.0019 -0.0045 0.105 Uiso 0.360(11) 1 calc R U P E 2
C11X C 0.2101(11) 0.0438(12) 0.0571(8) 0.094(3) Uani 0.360(11) 1 d D U P E 2
H11C H 0.2479 0.0800 0.0694 0.113 Uiso 0.360(11) 1 calc R U P E 2
H11D H 0.1970 0.0080 0.0775 0.113 Uiso 0.360(11) 1 calc R U P E 2
C12X C 0.1568(10) 0.0596(11) 0.0518(10) 0.108(3) Uani 0.360(11) 1 d D U P E 2
H12C H 0.1561 0.0741 0.0212 0.129 Uiso 0.360(11) 1 calc R U P E 2
H12D H 0.1158 0.0229 0.0585 0.129 Uiso 0.360(11) 1 calc R U P E 2
C13X C 0.1717(13) 0.1075(12) 0.0830(11) 0.123(4) Uani 0.360(11) 1 d D U P E 2
H13D H 0.1402 0.1203 0.0818 0.184 Uiso 0.360(11) 1 calc R U P E 2
H13E H 0.1726 0.0923 0.1129 0.184 Uiso 0.360(11) 1 calc R U P E 2
H13F H 0.2126 0.1431 0.0759 0.184 Uiso 0.360(11) 1 calc R U P E 2
C14 C 0.49049(17) 0.01672(18) 0.08170(12) 0.0471(8) Uani 1 1 d . . . . .
H14 H 0.4798 0.0259 0.1099 0.057 Uiso 1 1 calc R U . . .
C15 C 0.53644(16) 0.00046(17) 0.07904(11) 0.0449(8) Uani 1 1 d . . . . .
C16 C 0.55284(18) -0.0741(2) 0.15189(13) 0.0545(10) Uani 1 1 d . . . . .
C17 C 0.5160(2) -0.1271(2) 0.12791(17) 0.0643(11) Uani 1 1 d . . . . .
H17 H 0.5074 -0.1244 0.0974 0.077 Uiso 1 1 calc R U . . .
C18 C 0.4911(3) -0.1854(3) 0.1486(3) 0.0844(17) Uani 1 1 d . . . . .
H18 H 0.4650 -0.2223 0.1324 0.101 Uiso 1 1 calc R U . . .
C19 C 0.5050(3) -0.1886(3) 0.1934(2) 0.088(2) Uani 1 1 d . . . . .
H19 H 0.4870 -0.2277 0.2080 0.105 Uiso 1 1 calc R U . . .
C20 C 0.5438(3) -0.1361(4) 0.2157(2) 0.0856(19) Uani 1 1 d . . . . .
H20 H 0.5550 -0.1392 0.2454 0.103 Uiso 1 1 calc R U . . .
C21 C 0.5676(3) -0.0779(3) 0.19655(15) 0.0706(13) Uani 1 1 d . . . . .
H21 H 0.5935 -0.0413 0.2132 0.085 Uiso 1 1 calc R U . . .
C22 C 0.65826(17) 0.0534(2) 0.12540(12) 0.0532(10) Uani 1 1 d . . . . .
C23 C 0.6995(2) 0.0412(3) 0.14942(16) 0.0668(12) Uani 1 1 d . . . . .
H23 H 0.6848 0.0057 0.1681 0.080 Uiso 1 1 calc R U . . .
C24 C 0.7633(3) 0.0835(4) 0.1449(2) 0.0884(19) Uani 1 1 d . . . . .
H24 H 0.7924 0.0761 0.1603 0.106 Uiso 1 1 calc R U . . .
C25 C 0.7838(2) 0.1336(4) 0.1194(2) 0.103(3) Uani 1 1 d . . . . .
H25 H 0.8274 0.1616 0.1175 0.124 Uiso 1 1 calc R U . . .
C26 C 0.7437(3) 0.1465(3) 0.0954(2) 0.093(2) Uani 1 1 d . . . . .
H26 H 0.7595 0.1826 0.0772 0.112 Uiso 1 1 calc R U . . .
C27 C 0.6791(2) 0.1049(3) 0.09854(16) 0.0696(13) Uani 1 1 d . . . . .
H27 H 0.6505 0.1124 0.0825 0.084 Uiso 1 1 calc R U . . .
C28 C 0.54800(18) 0.0362(2) 0.17120(11) 0.0536(10) Uani 1 1 d . . . . .
C29 C 0.5809(2) 0.0997(2) 0.17943(15) 0.0631(11) Uani 1 1 d . . . . .
H29 H 0.6204 0.1252 0.1661 0.076 Uiso 1 1 calc R U . . .
C30 C 0.5550(3) 0.1255(3) 0.2076(2) 0.0813(15) Uani 1 1 d . . . . .
H30 H 0.5776 0.1688 0.2140 0.098 Uiso 1 1 calc R U . . .
C31 C 0.4973(3) 0.0891(3) 0.22630(17) 0.0784(15) Uani 1 1 d . . . . .
H31 H 0.4795 0.1074 0.2446 0.094 Uiso 1 1 calc R U . . .
C32 C 0.4655(2) 0.0264(3) 0.21858(14) 0.0707(14) Uani 1 1 d . . . . .
H32 H 0.4261 0.0013 0.2322 0.085 Uiso 1 1 calc R U . . .
C33 C 0.4901(2) -0.0010(3) 0.19097(12) 0.0604(11) Uani 1 1 d . . . . .
H33 H 0.4676 -0.0446 0.1857 0.072 Uiso 1 1 calc R U . . .
O1W O 0.1695(5) 0.6287(4) 0.0150(3) 0.091(2) Uiso 0.5 1 d . . P F 1
O4W O 0.2819(8) 0.4878(8) 0.3305(6) 0.135(4) Uiso 0.5 1 d . . P G 2
O2W O 0.4767(9) 0.6660(9) 0.4336(7) 0.158(6) Uiso 0.5 1 d . . P . .
O3W O 0.0000 0.0000 0.1267(12) 0.160(10) Uiso 0.5 3 d S . P . .
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'
Cl Cl 0.3639 0.7018 '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'
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 C22 115.2(2) . .
C16 P1 C15 113.82(19) . .
C22 P1 C15 110.82(17) . .
C16 P1 C28 104.5(2) . .
C22 P1 C28 106.51(19) . .
C15 P1 C28 104.94(18) . .
C2 N1 C1 124.1(3) . .
C2 N1 C6 118.6(3) . .
C1 N1 C6 117.3(3) . .
O1 C1 N1 119.5(4) . .
O1 C1 C5 124.3(3) . .
N1 C1 C5 116.2(3) . .
O2 C2 N1 121.0(3) . .
O2 C2 C3 120.4(3) . .
N1 C2 C3 118.7(3) . .
C4 C3 C15 119.9(3) . 10_655
C4 C3 C2 118.6(3) . .
C15 C3 C2 121.5(3) 10_655 .
C5 C4 C3 120.7(4) . .
C5 C4 C4 119.6(4) . 10_655
C3 C4 C4 119.7(4) . 10_655
C14 C5 C4 119.8(4) . .
C14 C5 C1 118.9(3) . .
C4 C5 C1 121.3(3) . .
N1 C6 C7 110.4(4) . .
N1 C6 H6A 109.6 . .
C7 C6 H6A 109.6 . .
N1 C6 H6B 109.6 . .
C7 C6 H6B 109.6 . .
H6A C6 H6B 108.1 . .
C8 C7 C10 111.9(7) . .
C8 C7 C6 113.4(5) . .
C10 C7 C6 110.0(6) . .
C8 C7 C10X 104.6(9) . .
C6 C7 C10X 92.0(7) . .
C8 C7 H7 107.0 . .
C10 C7 H7 107.0 . .
C6 C7 H7 107.0 . .
C7 C8 C9 111.0(7) . .
C7 C8 H8A 109.4 . .
C9 C8 H8A 109.4 . .
C7 C8 H8B 109.4 . .
C9 C8 H8B 109.4 . .
H8A C8 H8B 108.0 . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C11 C10 C7 115.9(8) . .
C11 C10 H10A 108.3 . .
C7 C10 H10A 108.3 . .
C11 C10 H10B 108.3 . .
C7 C10 H10B 108.3 . .
H10A C10 H10B 107.4 . .
C10 C11 C12 113.7(11) . .
C10 C11 H11A 108.8 . .
C12 C11 H11A 108.8 . .
C10 C11 H11B 108.8 . .
C12 C11 H11B 108.8 . .
H11A C11 H11B 107.7 . .
C13 C12 C11 112.1(14) . .
C13 C12 H12A 109.2 . .
C11 C12 H12A 109.2 . .
C13 C12 H12B 109.2 . .
C11 C12 H12B 109.2 . .
H12A C12 H12B 107.9 . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C11X C10X C7 99.6(14) . .
C11X C10X H10C 111.8 . .
C7 C10X H10C 111.8 . .
C11X C10X H10D 111.8 . .
C7 C10X H10D 111.8 . .
H10C C10X H10D 109.6 . .
C10X C11X C12X 107.0(17) . .
C10X C11X H11C 110.3 . .
C12X C11X H11C 110.3 . .
C10X C11X H11D 110.3 . .
C12X C11X H11D 110.3 . .
H11C C11X H11D 108.6 . .
C13X C12X C11X 104(2) . .
C13X C12X H12C 110.9 . .
C11X C12X H12C 110.9 . .
C13X C12X H12D 110.9 . .
C11X C12X H12D 110.9 . .
H12C C12X H12D 108.9 . .
C12X C13X H13D 109.5 . .
C12X C13X H13E 109.5 . .
H13D C13X H13E 109.5 . .
C12X C13X H13F 109.5 . .
H13D C13X H13F 109.5 . .
H13E C13X H13F 109.5 . .
C15 C14 C5 121.4(3) . .
C15 C14 H14 119.3 . .
C5 C14 H14 119.3 . .
C14 C15 C3 119.6(3) . 10_655
C14 C15 P1 117.2(3) . .
C3 C15 P1 123.1(3) 10_655 .
C17 C16 C21 120.4(5) . .
C17 C16 P1 121.7(3) . .
C21 C16 P1 117.5(4) . .
C16 C17 C18 119.7(5) . .
C16 C17 H17 120.2 . .
C18 C17 H17 120.2 . .
C19 C18 C17 119.4(6) . .
C19 C18 H18 120.3 . .
C17 C18 H18 120.3 . .
C20 C19 C18 120.0(5) . .
C20 C19 H19 120.0 . .
C18 C19 H19 120.0 . .
C19 C20 C21 121.8(6) . .
C19 C20 H20 119.1 . .
C21 C20 H20 119.1 . .
C20 C21 C16 118.6(6) . .
C20 C21 H21 120.7 . .
C16 C21 H21 120.7 . .
C27 C22 C23 121.8(4) . .
C27 C22 P1 118.2(3) . .
C23 C22 P1 120.0(4) . .
C24 C23 C22 117.5(6) . .
C24 C23 H23 121.2 . .
C22 C23 H23 121.2 . .
C25 C24 C23 121.2(6) . .
C25 C24 H24 119.4 . .
C23 C24 H24 119.4 . .
C24 C25 C26 122.2(5) . .
C24 C25 H25 118.9 . .
C26 C25 H25 118.9 . .
C25 C26 C27 118.6(6) . .
C25 C26 H26 120.7 . .
C27 C26 H26 120.7 . .
C22 C27 C26 118.7(6) . .
C22 C27 H27 120.7 . .
C26 C27 H27 120.7 . .
C29 C28 C33 120.1(4) . .
C29 C28 P1 120.6(3) . .
C33 C28 P1 119.0(4) . .
C28 C29 C30 119.0(5) . .
C28 C29 H29 120.5 . .
C30 C29 H29 120.5 . .
C31 C30 C29 120.8(6) . .
C31 C30 H30 119.6 . .
C29 C30 H30 119.6 . .
C32 C31 C30 119.9(5) . .
C32 C31 H31 120.1 . .
C30 C31 H31 120.1 . .
C31 C32 C33 120.8(5) . .
C31 C32 H32 119.6 . .
C33 C32 H32 119.6 . .
C32 C33 C28 119.2(5) . .
C32 C33 H33 120.4 . .
C28 C33 H33 120.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C16 1.794(4) .
P1 C22 1.798(4) .
P1 C15 1.812(3) .
P1 C28 1.817(4) .
O1 C1 1.224(5) .
O2 C2 1.236(4) .
N1 C2 1.384(5) .
N1 C1 1.407(5) .
N1 C6 1.466(5) .
C1 C5 1.443(6) .
C2 C3 1.454(5) .
C3 C4 1.409(5) .
C3 C15 1.412(5) 10_655
C4 C5 1.405(5) .
C4 C4 1.422(8) 10_655
C5 C14 1.396(5) .
C6 C7 1.578(7) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.499(10) .
C7 C10 1.518(10) .
C7 C10X 1.820(19) .
C7 H7 1.0000 .
C8 C9 1.528(9) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 C11 1.505(15) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.527(14) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.41(2) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C10X C11X 1.52(2) .
C10X H10C 0.9900 .
C10X H10D 0.9900 .
C11X C12X 1.56(2) .
C11X H11C 0.9900 .
C11X H11D 0.9900 .
C12X C13X 1.41(3) .
C12X H12C 0.9900 .
C12X H12D 0.9900 .
C13X H13D 0.9800 .
C13X H13E 0.9800 .
C13X H13F 0.9800 .
C14 C15 1.389(6) .
C14 H14 0.9500 .
C15 C3 1.412(5) 10_655
C16 C17 1.373(7) .
C16 C21 1.407(6) .
C17 C18 1.401(7) .
C17 H17 0.9500 .
C18 C19 1.400(11) .
C18 H18 0.9500 .
C19 C20 1.349(11) .
C19 H19 0.9500 .
C20 C21 1.381(9) .
C20 H20 0.9500 .
C21 H21 0.9500 .
C22 C27 1.377(7) .
C22 C23 1.403(6) .
C23 C24 1.401(8) .
C23 H23 0.9500 .
C24 C25 1.325(12) .
C24 H24 0.9500 .
C25 C26 1.391(12) .
C25 H25 0.9500 .
C26 C27 1.410(7) .
C26 H26 0.9500 .
C27 H27 0.9500 .
C28 C29 1.387(7) .
C28 C33 1.394(6) .
C29 C30 1.397(8) .
C29 H29 0.9500 .
C30 C31 1.374(10) .
C30 H30 0.9500 .
C31 C32 1.366(10) .
C31 H31 0.9500 .
C32 C33 1.393(8) .
C32 H32 0.9500 .
C33 H33 0.9500 .
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 O1 177.7(4) . .
C6 N1 C1 O1 -1.3(6) . .
C2 N1 C1 C5 -2.8(5) . .
C6 N1 C1 C5 178.1(3) . .
C1 N1 C2 O2 -174.0(3) . .
C6 N1 C2 O2 5.0(5) . .
C1 N1 C2 C3 6.5(5) . .
C6 N1 C2 C3 -174.4(3) . .
O2 C2 C3 C4 174.5(3) . .
N1 C2 C3 C4 -6.0(5) . .
O2 C2 C3 C15 -5.8(5) . 10_655
N1 C2 C3 C15 173.6(3) . 10_655
C15 C3 C4 C5 -177.5(3) 10_655 .
C2 C3 C4 C5 2.1(5) . .
C15 C3 C4 C4 1.9(6) 10_655 10_655
C2 C3 C4 C4 -178.4(4) . 10_655
C3 C4 C5 C14 -177.9(3) . .
C4 C4 C5 C14 2.6(6) 10_655 .
C3 C4 C5 C1 1.6(5) . .
C4 C4 C5 C1 -177.8(4) 10_655 .
O1 C1 C5 C14 -2.4(6) . .
N1 C1 C5 C14 178.1(3) . .
O1 C1 C5 C4 178.0(4) . .
N1 C1 C5 C4 -1.4(5) . .
C2 N1 C6 C7 101.5(4) . .
C1 N1 C6 C7 -79.4(5) . .
N1 C6 C7 C8 -57.4(7) . .
N1 C6 C7 C10 176.4(6) . .
N1 C6 C7 C10X -164.3(7) . .
C10 C7 C8 C9 -65.2(10) . .
C6 C7 C8 C9 169.7(7) . .
C10X C7 C8 C9 -91.5(10) . .
C8 C7 C10 C11 167.9(8) . .
C6 C7 C10 C11 -65.1(10) . .
C7 C10 C11 C12 -177.8(9) . .
C10 C11 C12 C13 166.0(12) . .
C8 C7 C10X C11X 143.1(13) . .
C6 C7 C10X C11X -102.1(14) . .
C7 C10X C11X C12X -166.2(15) . .
C10X C11X C12X C13X -144(2) . .
C4 C5 C14 C15 -2.2(6) . .
C1 C5 C14 C15 178.2(4) . .
C5 C14 C15 C3 -0.3(6) . 10_655
C5 C14 C15 P1 177.0(3) . .
C16 P1 C15 C14 106.0(3) . .
C22 P1 C15 C14 -122.3(3) . .
C28 P1 C15 C14 -7.7(3) . .
C16 P1 C15 C3 -76.9(3) . 10_655
C22 P1 C15 C3 54.9(4) . 10_655
C28 P1 C15 C3 169.5(3) . 10_655
C22 P1 C16 C17 -120.6(4) . .
C15 P1 C16 C17 9.0(4) . .
C28 P1 C16 C17 122.9(4) . .
C22 P1 C16 C21 66.9(4) . .
C15 P1 C16 C21 -163.5(3) . .
C28 P1 C16 C21 -49.6(4) . .
C21 C16 C17 C18 2.4(7) . .
P1 C16 C17 C18 -169.8(4) . .
C16 C17 C18 C19 -1.0(8) . .
C17 C18 C19 C20 -2.3(9) . .
C18 C19 C20 C21 4.2(9) . .
C19 C20 C21 C16 -2.7(8) . .
C17 C16 C21 C20 -0.7(7) . .
P1 C16 C21 C20 171.9(4) . .
C16 P1 C22 C27 162.8(4) . .
C15 P1 C22 C27 31.7(4) . .
C28 P1 C22 C27 -81.9(4) . .
C16 P1 C22 C23 -18.6(4) . .
C15 P1 C22 C23 -149.6(4) . .
C28 P1 C22 C23 96.8(4) . .
C27 C22 C23 C24 -0.5(7) . .
P1 C22 C23 C24 -179.1(4) . .
C22 C23 C24 C25 1.1(9) . .
C23 C24 C25 C26 -1.1(11) . .
C24 C25 C26 C27 0.4(11) . .
C23 C22 C27 C26 -0.1(8) . .
P1 C22 C27 C26 178.5(5) . .
C25 C26 C27 C22 0.2(9) . .
C16 P1 C28 C29 146.8(3) . .
C22 P1 C28 C29 24.4(4) . .
C15 P1 C28 C29 -93.2(3) . .
C16 P1 C28 C33 -39.7(4) . .
C22 P1 C28 C33 -162.1(3) . .
C15 P1 C28 C33 80.3(3) . .
C33 C28 C29 C30 -0.1(6) . .
P1 C28 C29 C30 173.3(4) . .
C28 C29 C30 C31 -1.4(8) . .
C29 C30 C31 C32 2.3(8) . .
C30 C31 C32 C33 -1.7(8) . .
C31 C32 C33 C28 0.2(7) . .
C29 C28 C33 C32 0.7(6) . .
P1 C28 C33 C32 -172.8(3) . .
