#------------------------------------------------------------------------------
#$Date: 2023-10-04 01:52:32 +0300 (Wed, 04 Oct 2023) $
#$Revision: 286642 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/40/7714095.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_7714095
loop_
_publ_author_name
'Siewert, Jan-Erik'
'Schumann, André'
'Wellnitz, Tim'
'Dankert, Fabian'
'Hering-Junghans, Christian'
_publ_section_title
;
 Triphosphiranes as Phosphinidene-Transfer Agents -- Synthesis of Regular
 and Chelating NHC Phosphinidene Adducts
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT02690F
_journal_year                    2023
_chemical_formula_moiety         'C22 H35 N2 P'
_chemical_formula_sum            'C22 H35 N2 P'
_chemical_formula_weight         358.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-09-21 deposited with the CCDC.	2023-09-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.2653(7)
_cell_length_b                   9.5140(2)
_cell_length_c                   15.0351(4)
_cell_measurement_reflns_used    9885
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      66.58
_cell_measurement_theta_min      2.92
_cell_volume                     4329.27(18)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3v2020.1 (Farrugia, 2020)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         microfocus
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34196
_diffrn_reflns_point_group_measured_fraction_full 0.930
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        65.979
_diffrn_reflns_theta_max         65.979
_diffrn_reflns_theta_min         2.920
_exptl_absorpt_coefficient_mu    1.151
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_correction_T_min  0.778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.100
_exptl_crystal_description       prism
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 2758 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.042(8)
_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     497
_refine_ls_number_reflns         7020
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0326
_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)+(0.0541P)²+0.2906P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0844
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_full    0.854
_reflns_Friedel_fraction_max     0.854
_reflns_number_gt                6730
_reflns_number_total             7020
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt02690f2.cif
_cod_data_source_block           ax1806_TipPIMe4_cmpd2c
_cod_database_code               7714095
_shelx_shelxl_version_number     2018/3
_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   0.778
_shelx_estimated_absorpt_t_max   0.945
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, 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
P1 P 0.89655(2) 0.68947(6) 0.85158(5) 0.03462(16) Uani 1 1 d . . . . .
N1 N 0.93707(6) 0.41255(19) 0.85954(15) 0.0292(4) Uani 1 1 d . . . . .
N2 N 0.86602(6) 0.4237(2) 0.87757(13) 0.0273(4) Uani 1 1 d . . . . .
C1 C 0.95413(7) 0.7575(2) 0.84859(19) 0.0287(5) Uani 1 1 d . . . . .
C2 C 0.97195(8) 0.8058(2) 0.76700(17) 0.0282(5) Uani 1 1 d . . . . .
C3 C 1.01348(8) 0.8692(2) 0.76646(17) 0.0278(5) Uani 1 1 d . . . . .
H3 H 1.025027 0.901991 0.711493 0.033 Uiso 1 1 calc R U . . .
C4 C 1.03861(7) 0.8863(2) 0.84264(17) 0.0261(4) Uani 1 1 d . . . . .
C5 C 1.02075(8) 0.8397(3) 0.92253(18) 0.0313(5) Uani 1 1 d . . . . .
H5 H 1.037410 0.850712 0.975626 0.038 Uiso 1 1 calc R U . . .
C6 C 0.97905(8) 0.7770(2) 0.92716(18) 0.0307(5) Uani 1 1 d . . . . .
C7 C 0.94667(8) 0.7915(3) 0.6801(2) 0.0376(6) Uani 1 1 d . . . . .
H7 H 0.926170 0.709760 0.687024 0.045 Uiso 1 1 calc R U . . .
C8 C 0.97612(11) 0.7605(4) 0.5998(2) 0.0508(7) Uani 1 1 d . . . . .
H8A H 0.994423 0.842890 0.586713 0.076 Uiso 1 1 calc R U . . .
H8B H 0.957598 0.738718 0.548123 0.076 Uiso 1 1 calc R U . . .
H8C H 0.995203 0.679931 0.613049 0.076 Uiso 1 1 calc R U . . .
C9 C 0.91814(11) 0.9207(4) 0.6627(2) 0.0581(8) Uani 1 1 d . . . . .
H9A H 0.898573 0.936727 0.713655 0.087 Uiso 1 1 calc R U . . .
H9B H 0.900333 0.905441 0.609133 0.087 Uiso 1 1 calc R U . . .
H9C H 0.937165 1.002921 0.654158 0.087 Uiso 1 1 calc R U . . .
C10 C 1.08355(7) 0.9578(2) 0.83666(17) 0.0301(5) Uani 1 1 d . . . . .
H10 H 1.094832 0.942567 0.774899 0.036 Uiso 1 1 calc R U . . .
C11 C 1.07874(9) 1.1160(3) 0.8497(3) 0.0511(8) Uani 1 1 d . . . . .
H11A H 1.057394 1.153024 0.806642 0.077 Uiso 1 1 calc R U . . .
H11B H 1.107438 1.161445 0.840599 0.077 Uiso 1 1 calc R U . . .
H11C H 1.068290 1.135092 0.910178 0.077 Uiso 1 1 calc R U . . .
C12 C 1.11767(9) 0.8974(4) 0.8999(3) 0.0549(8) Uani 1 1 d . . . . .
H12A H 1.108351 0.914328 0.961441 0.082 Uiso 1 1 calc R U . . .
H12B H 1.146268 0.942772 0.889472 0.082 Uiso 1 1 calc R U . . .
H12C H 1.120434 0.796008 0.889803 0.082 Uiso 1 1 calc R U . . .
C13A C 0.9590(8) 0.7359(19) 1.0208(11) 0.032(4) Uani 0.50(6) 1 d D U P A 1
H13A H 0.935041 0.665313 1.010689 0.039 Uiso 0.50(6) 1 calc R U P A 1
C14A C 0.9391(8) 0.861(3) 1.0617(18) 0.053(4) Uani 0.50(6) 1 d D . P A 1
H14A H 0.917093 0.900832 1.021072 0.079 Uiso 0.50(6) 1 calc R U P A 1
H14B H 0.924708 0.834190 1.117592 0.079 Uiso 0.50(6) 1 calc R U P A 1
H14C H 0.962122 0.930601 1.073597 0.079 Uiso 0.50(6) 1 calc R U P A 1
C15A C 0.9943(6) 0.668(3) 1.0827(19) 0.070(5) Uani 0.50(6) 1 d D . P A 1
H15A H 1.006899 0.585164 1.053544 0.105 Uiso 0.50(6) 1 calc R U P A 1
H15B H 1.017753 0.736318 1.094818 0.105 Uiso 0.50(6) 1 calc R U P A 1
H15C H 0.980339 0.639908 1.138814 0.105 Uiso 0.50(6) 1 calc R U P A 1
C13B C 0.9647(9) 0.730(2) 1.0126(14) 0.046(6) Uani 0.50(6) 1 d D U P A 2
H13B H 0.937104 0.674680 1.003012 0.055 Uiso 0.50(6) 1 calc R U P A 2
C14B C 0.9958(9) 0.638(4) 1.061(2) 0.089(8) Uani 0.50(6) 1 d D . P A 2
H14D H 0.983058 0.612272 1.118341 0.133 Uiso 0.50(6) 1 calc R U P A 2
H14E H 1.001276 0.553475 1.025604 0.133 Uiso 0.50(6) 1 calc R U P A 2
H14F H 1.023700 0.688472 1.070265 0.133 Uiso 0.50(6) 1 calc R U P A 2
C15B C 0.9520(13) 0.857(3) 1.075(2) 0.068(6) Uani 0.50(6) 1 d D . P A 2
H15D H 0.942343 0.821017 1.132716 0.102 Uiso 0.50(6) 1 calc R U P A 2
H15E H 0.977786 0.918009 1.082992 0.102 Uiso 0.50(6) 1 calc R U P A 2
H15F H 0.927976 0.910969 1.047551 0.102 Uiso 0.50(6) 1 calc R U P A 2
C16 C 0.90261(7) 0.5051(2) 0.86392(15) 0.0251(4) Uani 1 1 d . . . . .
C17 C 0.92147(8) 0.2745(2) 0.86872(17) 0.0325(5) Uani 1 1 d . . . . .
C18 C 0.87762(8) 0.2814(2) 0.87938(16) 0.0314(5) Uani 1 1 d . . . . .
C19 C 0.98214(8) 0.4463(3) 0.8339(3) 0.0492(8) Uani 1 1 d . . . . .
H19A H 0.981841 0.500401 0.778423 0.074 Uiso 1 1 calc R U . . .
H19B H 0.998843 0.359182 0.825035 0.074 Uiso 1 1 calc R U . . .
H19C H 0.996113 0.502090 0.880907 0.074 Uiso 1 1 calc R U . . .
C20 C 0.82198(7) 0.4813(3) 0.88614(19) 0.0364(6) Uani 1 1 d . . . . .
H20A H 0.820892 0.544420 0.937600 0.055 Uiso 1 1 calc R U . . .
H20B H 0.800749 0.404620 0.894477 0.055 Uiso 1 1 calc R U . . .
H20C H 0.814457 0.533831 0.832164 0.055 Uiso 1 1 calc R U . . .
C21 C 0.95170(11) 0.1509(3) 0.8675(3) 0.0510(7) Uani 1 1 d . . . . .
H21A H 0.934746 0.065155 0.879362 0.077 Uiso 1 1 calc R U . . .
H21B H 0.974414 0.162495 0.913410 0.077 Uiso 1 1 calc R U . . .
H21C H 0.965825 0.143740 0.809057 0.077 Uiso 1 1 calc R U . . .
C22 C 0.84390(10) 0.1678(3) 0.8917(2) 0.0424(6) Uani 1 1 d . . . . .
H22A H 0.858666 0.076130 0.892837 0.064 Uiso 1 1 calc R U . . .
H22B H 0.822768 0.170325 0.842291 0.064 Uiso 1 1 calc R U . . .
H22C H 0.828188 0.182551 0.947887 0.064 Uiso 1 1 calc R U . . .
P2 P 0.80535(2) 0.15642(6) 0.64818(4) 0.03089(14) Uani 1 1 d . . . . .
N3 N 0.79227(6) 0.3123(2) 0.48532(13) 0.0270(4) Uani 1 1 d . . . . .
N4 N 0.84809(6) 0.3738(2) 0.56691(14) 0.0273(4) Uani 1 1 d . . . . .
C23 C 0.74784(7) 0.0951(2) 0.63256(14) 0.0257(4) Uani 1 1 d . . . . .
C24 C 0.74046(7) -0.0502(2) 0.62160(15) 0.0260(4) Uani 1 1 d . . . . .
C25 C 0.69735(8) -0.1033(2) 0.62309(15) 0.0269(5) Uani 1 1 d . . . . .
H25 H 0.693025 -0.201769 0.617244 0.032 Uiso 1 1 calc R U . . .
C26 C 0.66075(7) -0.0171(2) 0.63281(15) 0.0273(5) Uani 1 1 d . . . . .
C27 C 0.66841(7) 0.1271(2) 0.64069(17) 0.0294(5) Uani 1 1 d . . . . .
H27 H 0.643787 0.188611 0.645027 0.035 Uiso 1 1 calc R U . . .
C28 C 0.71050(7) 0.1838(2) 0.64243(16) 0.0280(5) Uani 1 1 d . . . . .
C29 C 0.77843(8) -0.1534(3) 0.60713(18) 0.0317(5) Uani 1 1 d . . . . .
H29 H 0.806194 -0.097091 0.601605 0.038 Uiso 1 1 calc R U . . .
C30 C 0.77269(14) -0.2348(5) 0.5214(3) 0.0801(14) Uani 1 1 d . . . . .
H30A H 0.800129 -0.284920 0.507512 0.120 Uiso 1 1 calc R U . . .
H30B H 0.765681 -0.169559 0.472985 0.120 Uiso 1 1 calc R U . . .
H30C H 0.748562 -0.302632 0.528224 0.120 Uiso 1 1 calc R U . . .
C31 C 0.78427(13) -0.2519(5) 0.6842(3) 0.0739(12) Uani 1 1 d . . . . .
H31A H 0.757173 -0.306701 0.692680 0.111 Uiso 1 1 calc R U . . .
H31B H 0.790482 -0.197683 0.738229 0.111 Uiso 1 1 calc R U . . .
H31C H 0.808980 -0.315709 0.672161 0.111 Uiso 1 1 calc R U . . .
C32 C 0.61358(7) -0.0721(3) 0.63727(18) 0.0333(5) Uani 1 1 d . . . . .
H32 H 0.595990 -0.021141 0.591103 0.040 Uiso 1 1 calc R U . . .
C33 C 0.60941(9) -0.2290(3) 0.6186(2) 0.0408(6) Uani 1 1 d . . . . .
H33A H 0.622274 -0.250139 0.560259 0.061 Uiso 1 1 calc R U . . .
H33B H 0.578141 -0.255702 0.618779 0.061 Uiso 1 1 calc R U . . .
H33C H 0.625144 -0.281984 0.664614 0.061 Uiso 1 1 calc R U . . .
C34 C 0.59302(9) -0.0391(3) 0.7280(2) 0.0464(7) Uani 1 1 d . . . . .
H34A H 0.609775 -0.087043 0.774769 0.070 Uiso 1 1 calc R U . . .
H34B H 0.562302 -0.071632 0.728918 0.070 Uiso 1 1 calc R U . . .
H34C H 0.593818 0.062614 0.738307 0.070 Uiso 1 1 calc R U . . .
C35 C 0.71538(8) 0.3419(2) 0.6600(2) 0.0344(5) Uani 1 1 d . . . . .
H35 H 0.745061 0.371467 0.637497 0.041 Uiso 1 1 calc R U . . .
C36 C 0.71433(12) 0.3689(3) 0.7595(2) 0.0523(8) Uani 1 1 d . . . . .
H36A H 0.718025 0.469635 0.770742 0.078 Uiso 1 1 calc R U . . .
H36B H 0.738367 0.316834 0.788170 0.078 Uiso 1 1 calc R U . . .
H36C H 0.685939 0.337514 0.783701 0.078 Uiso 1 1 calc R U . . .
C37 C 0.68088(14) 0.4303(3) 0.6126(3) 0.0690(11) Uani 1 1 d . . . . .
H37A H 0.651724 0.411579 0.638387 0.104 Uiso 1 1 calc R U . . .
H37B H 0.680574 0.406360 0.549248 0.104 Uiso 1 1 calc R U . . .
H37C H 0.688067 0.530145 0.619722 0.104 Uiso 1 1 calc R U . . .
C38 C 0.81346(7) 0.2823(2) 0.56323(15) 0.0256(4) Uani 1 1 d . . . . .
C39 C 0.81343(8) 0.4234(2) 0.44158(17) 0.0290(5) Uani 1 1 d . . . . .
C40 C 0.84833(8) 0.4601(2) 0.49189(18) 0.0296(5) Uani 1 1 d . . . . .
C41 C 0.75883(9) 0.2248(3) 0.44360(18) 0.0396(6) Uani 1 1 d . . . . .
H41A H 0.764622 0.125881 0.457521 0.059 Uiso 1 1 calc R U . . .
H41B H 0.759725 0.238387 0.379010 0.059 Uiso 1 1 calc R U . . .
H41C H 0.729598 0.251166 0.466108 0.059 Uiso 1 1 calc R U . . .
C42 C 0.87840(8) 0.3805(3) 0.6411(2) 0.0402(6) Uani 1 1 d . . . . .
H42A H 0.861668 0.389589 0.696656 0.060 Uiso 1 1 calc R U . . .
H42B H 0.897879 0.462078 0.634109 0.060 Uiso 1 1 calc R U . . .
H42C H 0.896196 0.294540 0.642978 0.060 Uiso 1 1 calc R U . . .
C43 C 0.79568(9) 0.4839(3) 0.3577(2) 0.0435(6) Uani 1 1 d . . . . .
H43A H 0.813632 0.565061 0.340172 0.065 Uiso 1 1 calc R U . . .
H43B H 0.765056 0.513980 0.367063 0.065 Uiso 1 1 calc R U . . .
H43C H 0.796652 0.412735 0.310674 0.065 Uiso 1 1 calc R U . . .
C44 C 0.88262(10) 0.5702(3) 0.4783(2) 0.0442(6) Uani 1 1 d . . . . .
H44A H 0.877017 0.619359 0.422201 0.066 Uiso 1 1 calc R U . . .
H44B H 0.911870 0.526104 0.476285 0.066 Uiso 1 1 calc R U . . .
H44C H 0.881545 0.637481 0.527628 0.066 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'
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
_geom_angle_publ_flag
C16 P1 C1 104.47(9) . . ?
C16 N1 C17 109.98(18) . . ?
C16 N1 C19 125.9(2) . . ?
C17 N1 C19 123.3(2) . . ?
C16 N2 C18 110.37(19) . . ?
C16 N2 C20 123.0(2) . . ?
C18 N2 C20 126.6(2) . . ?
C6 C1 C2 118.54(19) . . ?
C6 C1 P1 121.70(19) . . ?
C2 C1 P1 119.38(18) . . ?
C3 C2 C1 119.3(2) . . ?
C3 C2 C7 119.2(2) . . ?
C1 C2 C7 121.6(2) . . ?
C4 C3 C2 122.8(2) . . ?
C4 C3 H3 118.6 . . ?
C2 C3 H3 118.6 . . ?
C3 C4 C5 117.6(2) . . ?
C3 C4 C10 119.6(2) . . ?
C5 C4 C10 122.7(2) . . ?
C4 C5 C6 122.0(2) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C1 119.7(2) . . ?
C5 C6 C13B 116.9(8) . . ?
C1 C6 C13B 123.3(8) . . ?
C5 C6 C13A 119.7(7) . . ?
C1 C6 C13A 120.4(7) . . ?
C2 C7 C9 111.1(2) . . ?
C2 C7 C8 113.7(2) . . ?
C9 C7 C8 110.5(3) . . ?
C2 C7 H7 107.0 . . ?
C9 C7 H7 107.0 . . ?
C8 C7 H7 107.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C12 C10 C4 113.7(2) . . ?
C12 C10 C11 111.0(3) . . ?
C4 C10 C11 110.35(18) . . ?
C12 C10 H10 107.2 . . ?
C4 C10 H10 107.2 . . ?
C11 C10 H10 107.2 . . ?
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 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14A C13A C15A 111.5(14) . . ?
C14A C13A C6 109.3(14) . . ?
C15A C13A C6 111.8(17) . . ?
C14A C13A H13A 108.0 . . ?
C15A C13A H13A 108.0 . . ?
C6 C13A H13A 108.0 . . ?
C13A C14A H14A 109.5 . . ?
C13A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C13A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C13A C15A H15A 109.5 . . ?
C13A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C13A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C6 C13B C14B 116(2) . . ?
C6 C13B C15B 111.9(17) . . ?
C14B C13B C15B 108.6(16) . . ?
C6 C13B H13B 106.8 . . ?
C14B C13B H13B 106.8 . . ?
C15B C13B H13B 106.8 . . ?
C13B C14B H14D 109.5 . . ?
C13B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C13B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C13B C15B H15D 109.5 . . ?
C13B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C13B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
N1 C16 N2 105.08(18) . . ?
N1 C16 P1 135.33(16) . . ?
N2 C16 P1 119.51(16) . . ?
C18 C17 N1 107.5(2) . . ?
C18 C17 C21 130.4(2) . . ?
N1 C17 C21 122.1(2) . . ?
C17 C18 N2 107.1(2) . . ?
C17 C18 C22 130.9(2) . . ?
N2 C18 C22 122.0(2) . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C38 P2 C23 104.62(10) . . ?
C38 N3 C39 110.23(19) . . ?
C38 N3 C41 125.3(2) . . ?
C39 N3 C41 123.3(2) . . ?
C38 N4 C40 110.31(19) . . ?
C38 N4 C42 123.2(2) . . ?
C40 N4 C42 126.5(2) . . ?
C24 C23 C28 118.0(2) . . ?
C24 C23 P2 118.21(16) . . ?
C28 C23 P2 123.28(17) . . ?
C25 C24 C23 120.0(2) . . ?
C25 C24 C29 118.1(2) . . ?
C23 C24 C29 121.9(2) . . ?
C26 C25 C24 122.2(2) . . ?
C26 C25 H25 118.9 . . ?
C24 C25 H25 118.9 . . ?
C25 C26 C27 117.2(2) . . ?
C25 C26 C32 123.5(2) . . ?
C27 C26 C32 119.3(2) . . ?
C28 C27 C26 122.5(2) . . ?
C28 C27 H27 118.7 . . ?
C26 C27 H27 118.7 . . ?
C27 C28 C23 120.0(2) . . ?
C27 C28 C35 118.3(2) . . ?
C23 C28 C35 121.6(2) . . ?
C31 C29 C30 110.6(3) . . ?
C31 C29 C24 112.3(2) . . ?
C30 C29 C24 111.3(2) . . ?
C31 C29 H29 107.4 . . ?
C30 C29 H29 107.4 . . ?
C24 C29 H29 107.4 . . ?
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 . . ?
C26 C32 C33 113.9(2) . . ?
C26 C32 C34 110.5(2) . . ?
C33 C32 C34 109.4(2) . . ?
C26 C32 H32 107.6 . . ?
C33 C32 H32 107.6 . . ?
C34 C32 H32 107.6 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C37 C35 C36 110.7(3) . . ?
C37 C35 C28 113.4(2) . . ?
C36 C35 C28 109.4(2) . . ?
C37 C35 H35 107.7 . . ?
C36 C35 H35 107.7 . . ?
C28 C35 H35 107.7 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N4 C38 N3 105.20(19) . . ?
N4 C38 P2 120.66(17) . . ?
N3 C38 P2 134.11(17) . . ?
C40 C39 N3 106.9(2) . . ?
C40 C39 C43 131.3(2) . . ?
N3 C39 C43 121.7(2) . . ?
C39 C40 N4 107.3(2) . . ?
C39 C40 C44 130.8(3) . . ?
N4 C40 C44 121.9(2) . . ?
N3 C41 H41A 109.5 . . ?
N3 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
N3 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
N4 C42 H42A 109.5 . . ?
N4 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
N4 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C39 C43 H43A 109.5 . . ?
C39 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C39 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C40 C44 H44A 109.5 . . ?
C40 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C40 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 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
P1 C16 1.773(2) . ?
P1 C1 1.859(2) . ?
N1 C16 1.367(3) . ?
N1 C17 1.402(3) . ?
N1 C19 1.453(3) . ?
N2 C16 1.367(3) . ?
N2 C18 1.399(3) . ?
N2 C20 1.447(3) . ?
C1 C6 1.414(4) . ?
C1 C2 1.417(4) . ?
C2 C3 1.394(3) . ?
C2 C7 1.520(4) . ?
C3 C4 1.384(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(4) . ?
C4 C10 1.523(3) . ?
C5 C6 1.398(3) . ?
C5 H5 0.9500 . ?
C6 C13B 1.43(2) . ?
C6 C13A 1.582(19) . ?
C7 C9 1.525(4) . ?
C7 C8 1.530(4) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C12 1.517(4) . ?
C10 C11 1.524(3) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13A C14A 1.47(3) . ?
C13A C15A 1.56(2) . ?
C13A H13A 1.0000 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
C13B C14B 1.48(3) . ?
C13B C15B 1.57(3) . ?
C13B H13B 1.0000 . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
C17 C18 1.338(4) . ?
C17 C21 1.490(4) . ?
C18 C22 1.498(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
P2 C38 1.768(2) . ?
P2 C23 1.850(2) . ?
N3 C38 1.366(3) . ?
N3 C39 1.400(3) . ?
N3 C41 1.452(3) . ?
N4 C38 1.364(3) . ?
N4 C40 1.395(3) . ?
N4 C42 1.446(3) . ?
C23 C24 1.410(3) . ?
C23 C28 1.418(3) . ?
C24 C25 1.400(3) . ?
C24 C29 1.527(3) . ?
C25 C26 1.386(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.397(3) . ?
C26 C32 1.522(3) . ?
C27 C28 1.384(3) . ?
C27 H27 0.9500 . ?
C28 C35 1.535(3) . ?
C29 C31 1.501(4) . ?
C29 C30 1.514(5) . ?
C29 H29 1.0000 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C33 1.524(4) . ?
C32 C34 1.532(4) . ?
C32 H32 1.0000 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C37 1.518(4) . ?
C35 C36 1.518(5) . ?
C35 H35 1.0000 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C39 C40 1.345(4) . ?
C39 C43 1.487(4) . ?
C40 C44 1.488(3) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 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
C16 P1 C1 C6 -79.9(2) . . . . ?
C16 P1 C1 C2 107.20(18) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
P1 C1 C2 C3 173.84(16) . . . . ?
C6 C1 C2 C7 -178.6(2) . . . . ?
P1 C1 C2 C7 -5.5(3) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C7 C2 C3 C4 180.0(2) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C2 C3 C4 C10 -179.5(2) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C10 C4 C5 C6 178.6(2) . . . . ?
C4 C5 C6 C1 1.1(4) . . . . ?
C4 C5 C6 C13B 178.6(11) . . . . ?
C4 C5 C6 C13A -175.6(9) . . . . ?
C2 C1 C6 C5 -1.5(3) . . . . ?
P1 C1 C6 C5 -174.47(17) . . . . ?
C2 C1 C6 C13B -178.9(12) . . . . ?
P1 C1 C6 C13B 8.1(12) . . . . ?
C2 C1 C6 C13A 175.1(9) . . . . ?
P1 C1 C6 C13A 2.2(10) . . . . ?
C3 C2 C7 C9 -88.9(3) . . . . ?
C1 C2 C7 C9 90.4(3) . . . . ?
C3 C2 C7 C8 36.5(3) . . . . ?
C1 C2 C7 C8 -144.2(2) . . . . ?
C3 C4 C10 C12 -144.7(3) . . . . ?
C5 C4 C10 C12 37.0(3) . . . . ?
C3 C4 C10 C11 89.9(3) . . . . ?
C5 C4 C10 C11 -88.5(3) . . . . ?
C5 C6 C13A C14A 81.8(14) . . . . ?
C1 C6 C13A C14A -94.9(13) . . . . ?
C5 C6 C13A C15A -42.2(17) . . . . ?
C1 C6 C13A C15A 141.1(14) . . . . ?
C5 C6 C13B C14B -52(2) . . . . ?
C1 C6 C13B C14B 125(2) . . . . ?
C5 C6 C13B C15B 73(2) . . . . ?
C1 C6 C13B C15B -109.8(17) . . . . ?
C17 N1 C16 N2 1.2(3) . . . . ?
C19 N1 C16 N2 171.2(3) . . . . ?
C17 N1 C16 P1 -175.6(2) . . . . ?
C19 N1 C16 P1 -5.6(4) . . . . ?
C18 N2 C16 N1 -1.5(3) . . . . ?
C20 N2 C16 N1 -180.0(2) . . . . ?
C18 N2 C16 P1 175.92(17) . . . . ?
C20 N2 C16 P1 -2.6(3) . . . . ?
C1 P1 C16 N1 -10.2(3) . . . . ?
C1 P1 C16 N2 173.35(19) . . . . ?
C16 N1 C17 C18 -0.4(3) . . . . ?
C19 N1 C17 C18 -170.7(3) . . . . ?
C16 N1 C17 C21 -179.3(3) . . . . ?
C19 N1 C17 C21 10.3(4) . . . . ?
N1 C17 C18 N2 -0.5(3) . . . . ?
C21 C17 C18 N2 178.3(3) . . . . ?
N1 C17 C18 C22 179.6(3) . . . . ?
C21 C17 C18 C22 -1.6(5) . . . . ?
C16 N2 C18 C17 1.3(3) . . . . ?
C20 N2 C18 C17 179.7(2) . . . . ?
C16 N2 C18 C22 -178.9(2) . . . . ?
C20 N2 C18 C22 -0.4(4) . . . . ?
C38 P2 C23 C24 124.44(17) . . . . ?
C38 P2 C23 C28 -64.0(2) . . . . ?
C28 C23 C24 C25 -1.7(3) . . . . ?
P2 C23 C24 C25 170.34(18) . . . . ?
C28 C23 C24 C29 177.8(2) . . . . ?
P2 C23 C24 C29 -10.2(3) . . . . ?
C23 C24 C25 C26 1.7(3) . . . . ?
C29 C24 C25 C26 -177.8(2) . . . . ?
C24 C25 C26 C27 0.4(3) . . . . ?
C24 C25 C26 C32 -178.2(2) . . . . ?
C25 C26 C27 C28 -2.5(4) . . . . ?
C32 C26 C27 C28 176.2(2) . . . . ?
C26 C27 C28 C23 2.5(4) . . . . ?
C26 C27 C28 C35 -174.4(2) . . . . ?
C24 C23 C28 C27 -0.3(3) . . . . ?
P2 C23 C28 C27 -171.93(18) . . . . ?
C24 C23 C28 C35 176.5(2) . . . . ?
P2 C23 C28 C35 4.9(3) . . . . ?
C25 C24 C29 C31 -67.9(4) . . . . ?
C23 C24 C29 C31 112.7(3) . . . . ?
C25 C24 C29 C30 56.8(4) . . . . ?
C23 C24 C29 C30 -122.7(3) . . . . ?
C25 C26 C32 C33 -7.2(3) . . . . ?
C27 C26 C32 C33 174.2(2) . . . . ?
C25 C26 C32 C34 116.4(3) . . . . ?
C27 C26 C32 C34 -62.2(3) . . . . ?
C27 C28 C35 C37 -40.5(4) . . . . ?
C23 C28 C35 C37 142.6(3) . . . . ?
C27 C28 C35 C36 83.6(3) . . . . ?
C23 C28 C35 C36 -93.3(3) . . . . ?
C40 N4 C38 N3 0.1(2) . . . . ?
C42 N4 C38 N3 177.8(2) . . . . ?
C40 N4 C38 P2 178.47(16) . . . . ?
C42 N4 C38 P2 -3.8(3) . . . . ?
C39 N3 C38 N4 -0.8(2) . . . . ?
C41 N3 C38 N4 166.9(2) . . . . ?
C39 N3 C38 P2 -178.86(19) . . . . ?
C41 N3 C38 P2 -11.1(4) . . . . ?
C23 P2 C38 N4 164.07(18) . . . . ?
C23 P2 C38 N3 -18.1(3) . . . . ?
C38 N3 C39 C40 1.2(3) . . . . ?
C41 N3 C39 C40 -166.8(2) . . . . ?
C38 N3 C39 C43 -176.1(2) . . . . ?
C41 N3 C39 C43 15.9(4) . . . . ?
N3 C39 C40 N4 -1.1(3) . . . . ?
C43 C39 C40 N4 175.8(3) . . . . ?
N3 C39 C40 C44 179.6(3) . . . . ?
C43 C39 C40 C44 -3.5(5) . . . . ?
C38 N4 C40 C39 0.7(3) . . . . ?
C42 N4 C40 C39 -177.0(2) . . . . ?
C38 N4 C40 C44 -179.9(2) . . . . ?
C42 N4 C40 C44 2.4(4) . . . . ?
