#------------------------------------------------------------------------------
#$Date: 2023-09-05 22:05:20 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286028 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/93/1569381.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_1569381
loop_
_publ_author_name
'Löwe, Pawel'
'Wünsche, Marius A'
'Purtscher, Felix R. S.'
'Gamper, Jakob'
'Hofer, Thomas S.'
'Wilm, Lukas F. B.'
'Röthel, Maike B'
'Dielmann, Fabian'
_publ_section_title
;
 Terminal methylene phosphonium ions: precursors for transient
 monosubstituted phosphinocarbenes.
;
_journal_issue                   29
_journal_name_full               'Chemical science'
_journal_page_first              7928
_journal_page_last               7935
_journal_paper_doi               10.1039/d3sc02899b
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C23 H47 I N6 P, I'
_chemical_formula_sum            'C23 H47 I2 N6 P'
_chemical_formula_weight         692.43
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2023-02-23 deposited with the CCDC.	2023-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                106.682(2)
_cell_angle_beta                 106.508(2)
_cell_angle_gamma                103.779(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5526(3)
_cell_length_b                   12.6149(5)
_cell_length_c                   14.1053(5)
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.27
_cell_measurement_theta_min      2.31
_cell_volume                     1463.45(10)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_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  0.0342
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26020
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.325
_diffrn_reflns_theta_min         1.629
_diffrn_source_current           0.59
_diffrn_source_power             0.0295
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.225
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1071 before and 0.0442 after correction.
The Ratio of minimum to maximum transmission is 0.7411.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.574
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.061
_refine_diff_density_max         1.948
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         8672
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0330
_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)+(0.0428P)²+1.4620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0873
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7751
_reflns_number_total             8672
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc02899b2.cif
_cod_data_source_block           p-1_a
_cod_depositor_comments
'Adding full bibliography for 1569380--1569388.cif.'
_cod_original_cell_volume        1463.44(9)
_cod_database_code               1569381
_shelxl_version_number           2013-4
_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_max   0.876
_shelx_estimated_absorpt_t_min   0.362
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: I1B(0.96) I1(0.04)
3.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B), C6(H6A,H6B)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C19(H19A,H19B,H19C), C17(H17A,H17B,H17C), C11(H11A,H11B,
 H11C), C10(H10A,H10B,H10C), C22(H22A,H22B,H22C), C21(H21A,H21B,H21C), C18(H18A,
 H18B,H18C), C15(H15A,H15B,H15C), C23(H23A,H23B,H23C), C9(H9A,H9B,H9C),
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_olex2_submission_original_sample_id PL564
_olex2_submission_special_instructions 'No special instructions were received'
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
I1B I 0.67065(2) 0.22057(2) 0.53614(2) 0.01558(5) Uani 0.96 1 d . . P A 1
I2 I 0.74456(2) 0.15455(2) 0.27594(2) 0.02370(5) Uani 1 1 d . . . . .
P1 P 0.57704(7) 0.25005(5) 0.68684(5) 0.01265(11) Uani 1 1 d . . . . .
N2 N 0.6619(2) 0.56401(17) 0.72961(17) 0.0166(4) Uani 1 1 d . . . . .
N3 N 0.4021(2) 0.48486(18) 0.65065(17) 0.0164(4) Uani 1 1 d . . . . .
N5 N 0.7822(2) 0.11633(18) 0.85195(17) 0.0149(4) Uani 1 1 d . . . . .
N6 N 0.5987(2) 0.16671(18) 0.90277(17) 0.0150(4) Uani 1 1 d . . . . .
N4 N 0.6925(2) 0.25588(17) 0.79462(16) 0.0142(4) Uani 1 1 d . . . . .
N1 N 0.5332(2) 0.36227(18) 0.69680(17) 0.0163(4) Uani 1 1 d . . . . .
C16 C 0.8767(3) 0.0900(2) 0.7861(2) 0.0153(4) Uani 1 1 d . . . . .
C2 C 0.5351(3) 0.4638(2) 0.69225(19) 0.0144(4) Uani 1 1 d . . . . .
C3 C 0.6044(3) 0.6619(2) 0.7268(2) 0.0207(5) Uani 1 1 d . . . . .
H3A H 0.6707 0.7189 0.7078 0.025 Uiso 1 1 calc R U . . .
H3B H 0.6004 0.7039 0.7964 0.025 Uiso 1 1 calc R U . . .
C5 C 0.6891(3) 0.18204(19) 0.84520(19) 0.0134(4) Uani 1 1 d . . . . .
C1 C 0.4116(3) 0.1175(2) 0.6293(2) 0.0198(5) Uani 1 1 d . . . B 1
H1A H 0.3383 0.1156 0.5635 0.030 Uiso 1 1 calc R U . B 1
H1B H 0.3605 0.1149 0.6801 0.030 Uiso 1 1 calc R U . B 1
H1C H 0.4453 0.0492 0.6125 0.030 Uiso 1 1 calc R U . B 1
C20 C 0.5353(3) 0.2522(2) 0.9580(2) 0.0164(4) Uani 1 1 d . . . . .
C19 C 0.7695(3) 0.0033(2) 0.6735(2) 0.0220(5) Uani 1 1 d . . . . .
H19A H 0.7016 -0.0660 0.6771 0.033 Uiso 1 1 calc R U . . .
H19B H 0.8321 -0.0214 0.6331 0.033 Uiso 1 1 calc R U . . .
H19C H 0.7057 0.0414 0.6377 0.033 Uiso 1 1 calc R U . . .
C17 C 0.9777(3) 0.2030(2) 0.7852(2) 0.0191(5) Uani 1 1 d . . . . .
H17A H 0.9110 0.2388 0.7487 0.029 Uiso 1 1 calc R U . . .
H17B H 1.0458 0.1843 0.7474 0.029 Uiso 1 1 calc R U . . .
H17C H 1.0415 0.2584 0.8589 0.029 Uiso 1 1 calc R U . . .
C11 C 0.9163(3) 0.7178(2) 0.8470(2) 0.0271(6) Uani 1 1 d . . . . .
H11A H 0.9295 0.7335 0.7854 0.041 Uiso 1 1 calc R U . . .
H11B H 1.0186 0.7351 0.9008 0.041 Uiso 1 1 calc R U . . .
H11C H 0.8639 0.7680 0.8781 0.041 Uiso 1 1 calc R U . . .
C8 C 0.8177(3) 0.5878(2) 0.8109(2) 0.0181(5) Uani 1 1 d . . . . .
C10 C 0.9010(3) 0.5133(2) 0.7605(2) 0.0238(5) Uani 1 1 d . . . . .
H10A H 0.8450 0.4297 0.7421 0.036 Uiso 1 1 calc R U . . .
H10B H 1.0075 0.5362 0.8114 0.036 Uiso 1 1 calc R U . . .
H10C H 0.9040 0.5260 0.6957 0.036 Uiso 1 1 calc R U . . .
C22 C 0.4248(3) 0.1851(2) 0.9982(2) 0.0227(5) Uani 1 1 d . . . . .
H22A H 0.3488 0.1128 0.9390 0.034 Uiso 1 1 calc R U . . .
H22B H 0.3701 0.2350 1.0267 0.034 Uiso 1 1 calc R U . . .
H22C H 0.4848 0.1647 1.0549 0.034 Uiso 1 1 calc R U . . .
C21 C 0.6706(3) 0.3538(2) 1.0522(2) 0.0241(5) Uani 1 1 d . . . . .
H21A H 0.7252 0.3226 1.1016 0.036 Uiso 1 1 calc R U . . .
H21B H 0.6304 0.4101 1.0896 0.036 Uiso 1 1 calc R U . . .
H21C H 0.7430 0.3937 1.0257 0.036 Uiso 1 1 calc R U . . .
C18 C 0.9855(3) 0.0336(2) 0.8378(2) 0.0221(5) Uani 1 1 d . . . . .
H18A H 1.0524 0.0879 0.9113 0.033 Uiso 1 1 calc R U . . .
H18B H 1.0504 0.0167 0.7968 0.033 Uiso 1 1 calc R U . . .
H18C H 0.9236 -0.0401 0.8385 0.033 Uiso 1 1 calc R U . . .
C4 C 0.4440(3) 0.5999(2) 0.6411(2) 0.0209(5) Uani 1 1 d . . . . .
H4A H 0.3718 0.6414 0.6553 0.025 Uiso 1 1 calc R U . . .
H4B H 0.4456 0.5920 0.5696 0.025 Uiso 1 1 calc R U . . .
C15 C 0.2518(3) 0.3134(2) 0.4804(2) 0.0224(5) Uani 1 1 d . . . . .
H15A H 0.2867 0.3612 0.4422 0.034 Uiso 1 1 calc R U . . .
H15B H 0.1477 0.2551 0.4348 0.034 Uiso 1 1 calc R U . . .
H15C H 0.3246 0.2725 0.4988 0.034 Uiso 1 1 calc R U . . .
C7 C 0.6325(3) 0.0841(2) 0.9525(2) 0.0187(5) Uani 1 1 d . . . . .
H7A H 0.5354 0.0220 0.9391 0.022 Uiso 1 1 calc R U . . .
H7B H 0.6908 0.1256 1.0307 0.022 Uiso 1 1 calc R U . . .
C6 C 0.7308(3) 0.0321(2) 0.8989(2) 0.0207(5) Uani 1 1 d . . . . .
H6A H 0.8207 0.0274 0.9516 0.025 Uiso 1 1 calc R U . . .
H6B H 0.6684 -0.0476 0.8430 0.025 Uiso 1 1 calc R U . . .
C23 C 0.4400(3) 0.2993(3) 0.8847(2) 0.0229(5) Uani 1 1 d . . . . .
H23A H 0.5074 0.3455 0.8591 0.034 Uiso 1 1 calc R U . . .
H23B H 0.3953 0.3497 0.9245 0.034 Uiso 1 1 calc R U . . .
H23C H 0.3558 0.2331 0.8236 0.034 Uiso 1 1 calc R U . . .
C12 C 0.2463(3) 0.3928(2) 0.5822(2) 0.0182(5) Uani 1 1 d . . . . .
C9 C 0.8002(3) 0.5637(2) 0.9073(2) 0.0227(5) Uani 1 1 d . . . . .
H9A H 0.7464 0.6127 0.9383 0.034 Uiso 1 1 calc R U . . .
H9B H 0.9035 0.5828 0.9608 0.034 Uiso 1 1 calc R U . . .
H9C H 0.7395 0.4802 0.8849 0.034 Uiso 1 1 calc R U . . .
C13 C 0.1892(3) 0.3236(3) 0.6446(2) 0.0236(5) Uani 1 1 d . . . . .
H13A H 0.2574 0.2793 0.6624 0.035 Uiso 1 1 calc R U . . .
H13B H 0.0826 0.2685 0.6009 0.035 Uiso 1 1 calc R U . . .
H13C H 0.1910 0.3784 0.7105 0.035 Uiso 1 1 calc R U . . .
C14 C 0.1314(3) 0.4546(3) 0.5512(2) 0.0261(6) Uani 1 1 d . . . . .
H14A H 0.1261 0.5062 0.6160 0.039 Uiso 1 1 calc R U . . .
H14B H 0.0280 0.3954 0.5053 0.039 Uiso 1 1 calc R U . . .
H14C H 0.1663 0.5019 0.5126 0.039 Uiso 1 1 calc R U . . .
I1 I 0.3440(8) 0.0843(5) 0.6338(5) 0.0353(12) Uani 0.04 1 d . . P A 2
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'
I I -0.4742 1.8119 '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'
P P 0.1023 0.0942 '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
N4 P1 I1B 115.67(8) . . ?
N4 P1 C1 109.76(12) . . ?
N4 P1 I1 105.79(16) . . ?
N1 P1 I1B 104.18(8) . . ?
N1 P1 N4 114.02(11) . . ?
N1 P1 C1 113.20(12) . . ?
N1 P1 I1 108.74(17) . . ?
C1 P1 I1B 99.08(10) . . ?
C2 N2 C3 107.6(2) . . ?
C2 N2 C8 125.0(2) . . ?
C3 N2 C8 119.9(2) . . ?
C2 N3 C4 108.8(2) . . ?
C2 N3 C12 125.4(2) . . ?
C4 N3 C12 120.8(2) . . ?
C5 N5 C16 127.7(2) . . ?
C5 N5 C6 109.64(19) . . ?
C6 N5 C16 118.25(19) . . ?
C5 N6 C20 128.43(19) . . ?
C5 N6 C7 109.79(19) . . ?
C7 N6 C20 115.50(19) . . ?
C5 N4 P1 132.41(17) . . ?
C2 N1 P1 159.6(2) . . ?
N5 C16 C19 109.6(2) . . ?
N5 C16 C17 111.04(19) . . ?
N5 C16 C18 107.8(2) . . ?
C19 C16 C17 111.5(2) . . ?
C19 C16 C18 109.1(2) . . ?
C17 C16 C18 107.6(2) . . ?
N3 C2 N2 110.1(2) . . ?
N1 C2 N2 127.6(2) . . ?
N1 C2 N3 122.2(2) . . ?
N2 C3 H3A 111.2 . . ?
N2 C3 H3B 111.2 . . ?
N2 C3 C4 102.71(19) . . ?
H3A C3 H3B 109.1 . . ?
C4 C3 H3A 111.2 . . ?
C4 C3 H3B 111.2 . . ?
N5 C5 N6 110.4(2) . . ?
N4 C5 N5 124.5(2) . . ?
N4 C5 N6 125.0(2) . . ?
P1 C1 H1A 109.5 . . ?
P1 C1 H1B 109.5 . . ?
P1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N6 C20 C22 106.9(2) . . ?
N6 C20 C21 108.7(2) . . ?
N6 C20 C23 113.7(2) . . ?
C21 C20 C22 110.2(2) . . ?
C23 C20 C22 106.8(2) . . ?
C23 C20 C21 110.5(2) . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
N2 C8 C11 108.4(2) . . ?
N2 C8 C10 109.9(2) . . ?
N2 C8 C9 110.6(2) . . ?
C10 C8 C11 107.7(2) . . ?
C9 C8 C11 109.1(2) . . ?
C9 C8 C10 111.0(2) . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C4 C3 101.26(19) . . ?
N3 C4 H4A 111.5 . . ?
N3 C4 H4B 111.5 . . ?
C3 C4 H4A 111.5 . . ?
C3 C4 H4B 111.5 . . ?
H4A C4 H4B 109.3 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
N6 C7 H7A 111.0 . . ?
N6 C7 H7B 111.0 . . ?
N6 C7 C6 103.8(2) . . ?
H7A C7 H7B 109.0 . . ?
C6 C7 H7A 111.0 . . ?
C6 C7 H7B 111.0 . . ?
N5 C6 C7 102.82(19) . . ?
N5 C6 H6A 111.2 . . ?
N5 C6 H6B 111.2 . . ?
C7 C6 H6A 111.2 . . ?
C7 C6 H6B 111.2 . . ?
H6A C6 H6B 109.1 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N3 C12 C15 110.2(2) . . ?
N3 C12 C13 110.4(2) . . ?
N3 C12 C14 108.2(2) . . ?
C15 C12 C13 112.3(2) . . ?
C15 C12 C14 108.3(2) . . ?
C13 C12 C14 107.3(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
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
I1B P1 2.4983(6) . ?
P1 N4 1.574(2) . ?
P1 N1 1.550(2) . ?
P1 C1 1.785(3) . ?
P1 I1 2.413(7) . ?
N2 C2 1.367(3) . ?
N2 C3 1.472(3) . ?
N2 C8 1.496(3) . ?
N3 C2 1.362(3) . ?
N3 C4 1.466(3) . ?
N3 C12 1.487(3) . ?
N5 C16 1.493(3) . ?
N5 C5 1.355(3) . ?
N5 C6 1.465(3) . ?
N6 C5 1.361(3) . ?
N6 C20 1.495(3) . ?
N6 C7 1.461(3) . ?
N4 C5 1.326(3) . ?
N1 C2 1.296(3) . ?
C16 C19 1.521(4) . ?
C16 C17 1.525(3) . ?
C16 C18 1.530(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.501(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C20 C22 1.530(4) . ?
C20 C21 1.528(4) . ?
C20 C23 1.526(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 C8 1.532(3) . ?
C8 C10 1.521(4) . ?
C8 C9 1.521(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 C12 1.520(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C6 1.516(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C12 C13 1.523(4) . ?
C12 C14 1.527(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
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
I1B P1 N4 C5 -109.3(2) . . . . ?
I1B P1 N1 C2 -29.4(6) . . . . ?
P1 N4 C5 N5 107.9(3) . . . . ?
P1 N4 C5 N6 -76.2(3) . . . . ?
P1 N1 C2 N2 -48.2(7) . . . . ?
P1 N1 C2 N3 134.4(5) . . . . ?
N2 C3 C4 N3 29.9(2) . . . . ?
N6 C7 C6 N5 17.4(3) . . . . ?
N4 P1 N1 C2 97.6(6) . . . . ?
N1 P1 N4 C5 129.9(2) . . . . ?
C16 N5 C5 N6 167.8(2) . . . . ?
C16 N5 C5 N4 -15.8(4) . . . . ?
C16 N5 C6 C7 -176.7(2) . . . . ?
C2 N2 C3 C4 -25.1(3) . . . . ?
C2 N2 C8 C11 -168.8(2) . . . . ?
C2 N2 C8 C10 73.7(3) . . . . ?
C2 N2 C8 C9 -49.2(3) . . . . ?
C2 N3 C4 C3 -26.1(3) . . . . ?
C2 N3 C12 C15 -60.5(3) . . . . ?
C2 N3 C12 C13 64.1(3) . . . . ?
C2 N3 C12 C14 -178.7(2) . . . . ?
C3 N2 C2 N3 9.2(3) . . . . ?
C3 N2 C2 N1 -168.3(2) . . . . ?
C3 N2 C8 C11 -22.9(3) . . . . ?
C3 N2 C8 C10 -140.4(2) . . . . ?
C3 N2 C8 C9 96.7(3) . . . . ?
C5 N5 C16 C19 -72.3(3) . . . . ?
C5 N5 C16 C17 51.4(3) . . . . ?
C5 N5 C16 C18 169.1(2) . . . . ?
C5 N5 C6 C7 -18.5(3) . . . . ?
C5 N6 C20 C22 172.9(2) . . . . ?
C5 N6 C20 C21 -68.2(3) . . . . ?
C5 N6 C20 C23 55.3(3) . . . . ?
C5 N6 C7 C6 -11.4(3) . . . . ?
C1 P1 N4 C5 1.7(3) . . . . ?
C1 P1 N1 C2 -135.9(6) . . . . ?
C20 N6 C5 N5 150.3(2) . . . . ?
C20 N6 C5 N4 -26.1(4) . . . . ?
C20 N6 C7 C6 -166.0(2) . . . . ?
C8 N2 C2 N3 158.6(2) . . . . ?
C8 N2 C2 N1 -19.0(4) . . . . ?
C8 N2 C3 C4 -176.3(2) . . . . ?
C4 N3 C2 N2 11.3(3) . . . . ?
C4 N3 C2 N1 -171.0(2) . . . . ?
C4 N3 C12 C15 91.4(3) . . . . ?
C4 N3 C12 C13 -144.0(2) . . . . ?
C4 N3 C12 C14 -26.8(3) . . . . ?
C7 N6 C5 N5 -0.1(3) . . . . ?
C7 N6 C5 N4 -176.5(2) . . . . ?
C7 N6 C20 C22 -38.1(3) . . . . ?
C7 N6 C20 C21 80.8(3) . . . . ?
C7 N6 C20 C23 -155.6(2) . . . . ?
C6 N5 C16 C19 81.4(3) . . . . ?
C6 N5 C16 C17 -154.9(2) . . . . ?
C6 N5 C16 C18 -37.2(3) . . . . ?
C6 N5 C5 N6 12.3(3) . . . . ?
C6 N5 C5 N4 -171.3(2) . . . . ?
C12 N3 C2 N2 166.0(2) . . . . ?
C12 N3 C2 N1 -16.3(4) . . . . ?
C12 N3 C4 C3 177.8(2) . . . . ?
I1 P1 N4 C5 10.5(3) . . . . ?
I1 P1 N1 C2 -144.6(6) . . . . ?
