#------------------------------------------------------------------------------
#$Date: 2020-08-08 02:15:15 +0300 (Sat, 08 Aug 2020) $
#$Revision: 255188 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/86/4038661.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_4038661
loop_
_publ_author_name
'Hirakawa, Fumiya'
'Nakagawa, Hiroshi'
'Honda, Shunya'
'Ishida, Shintaro'
'Iwamoto, Takeaki'
_publ_section_title
;
 Trialkylphosphines Having a Bulky Phosphacyclopentane Backbone:
 Structural and Redox Properties Depending on the Exocyclic Alkyl Groups
 and EPR Observation of a Persistent Trialkylphosphine Radical Cation.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01393
_journal_year                    2020
_chemical_formula_sum            'C20 H49 P Si4'
_chemical_formula_weight         432.92
_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
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                109.976(3)
_cell_angle_beta                 92.190(4)
_cell_angle_gamma                108.632(4)
_cell_formula_units_Z            2
_cell_length_a                   8.365(2)
_cell_length_b                   11.304(3)
_cell_length_c                   16.179(4)
_cell_measurement_reflns_used    2432
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.92
_cell_measurement_theta_min      2.68
_cell_volume                     1343.7(6)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6564
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         1.358
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5093
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.070
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.728
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0532
_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)+(0.0550P)²+1.7265P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1334
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3817
_reflns_number_total             4860
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01393_si_003.cif
_cod_data_source_block           fh30aa_CCDC-1991936
_cod_database_code               4038661
_shelx_shelxl_version_number     2018/1
_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.
;
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.972
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
P1 P 0.69819(10) -0.08450(6) 0.23150(5) 0.0132(2) Uani 1 1 d . . . . .
C1 C 0.7041(4) 0.0848(3) 0.31486(18) 0.0150(7) Uani 1 1 d . . . . .
C2 C 0.5579(4) 0.0313(3) 0.36555(19) 0.0196(7) Uani 1 1 d . . . . .
H1 H 0.602875 -0.000463 0.408117 0.023 Uiso 1 1 calc R U . . .
H2 H 0.520089 0.105627 0.399985 0.023 Uiso 1 1 calc R U . . .
C3 C 0.4056(4) -0.0838(3) 0.30040(19) 0.0180(7) Uani 1 1 d . . . . .
H3 H 0.341825 -0.047565 0.268581 0.022 Uiso 1 1 calc R U . . .
H4 H 0.327230 -0.128866 0.333707 0.022 Uiso 1 1 calc R U . . .
C4 C 0.4677(4) -0.1885(3) 0.23124(18) 0.0141(7) Uani 1 1 d . . . . .
Si1 Si 0.65714(12) 0.22580(7) 0.28900(6) 0.0185(2) Uani 1 1 d . . . . .
C5 C 0.6605(5) 0.3605(3) 0.3979(2) 0.0313(9) Uani 1 1 d . . . . .
H5 H 0.774149 0.397911 0.434328 0.047 Uiso 1 1 calc R U . . .
H6 H 0.574811 0.321397 0.429938 0.047 Uiso 1 1 calc R U . . .
H7 H 0.634193 0.432263 0.385991 0.047 Uiso 1 1 calc R U . . .
C6 C 0.8146(4) 0.3181(3) 0.2318(2) 0.0251(8) Uani 1 1 d . . . . .
H8 H 0.875981 0.410840 0.273157 0.038 Uiso 1 1 calc R U . . .
H9 H 0.753099 0.318977 0.179327 0.038 Uiso 1 1 calc R U . . .
H10 H 0.896483 0.272602 0.213174 0.038 Uiso 1 1 calc R U . . .
C7 C 0.4368(5) 0.1746(3) 0.2259(2) 0.0290(9) Uani 1 1 d . . . . .
H11 H 0.427245 0.249354 0.210899 0.044 Uiso 1 1 calc R U . . .
H12 H 0.351158 0.151760 0.263014 0.044 Uiso 1 1 calc R U . . .
H13 H 0.417176 0.096178 0.171008 0.044 Uiso 1 1 calc R U . . .
Si2 Si 0.91908(11) 0.16199(7) 0.39617(5) 0.0176(2) Uani 1 1 d . . . . .
C8 C 0.8802(5) 0.2183(3) 0.5145(2) 0.0309(9) Uani 1 1 d . . . . .
H14 H 0.818012 0.139439 0.528117 0.046 Uiso 1 1 calc R U . . .
H15 H 0.812169 0.276492 0.522211 0.046 Uiso 1 1 calc R U . . .
H16 H 0.989959 0.268306 0.554880 0.046 Uiso 1 1 calc R U . . .
C9 C 1.0795(4) 0.3126(3) 0.3838(2) 0.0280(8) Uani 1 1 d . . . . .
H17 H 1.185286 0.343248 0.425714 0.042 Uiso 1 1 calc R U . . .
H18 H 1.032917 0.385122 0.396674 0.042 Uiso 1 1 calc R U . . .
H19 H 1.103817 0.288014 0.322726 0.042 Uiso 1 1 calc R U . . .
C10 C 1.0396(4) 0.0456(3) 0.3852(2) 0.0236(8) Uani 1 1 d . . . . .
H20 H 1.069621 0.018978 0.325294 0.035 Uiso 1 1 calc R U . . .
H21 H 0.968190 -0.034610 0.394792 0.035 Uiso 1 1 calc R U . . .
H22 H 1.144208 0.091307 0.429702 0.035 Uiso 1 1 calc R U . . .
Si3 Si 0.50264(11) -0.31378(7) 0.28019(5) 0.0163(2) Uani 1 1 d . . . . .
C11 C 0.6290(5) -0.4105(3) 0.2132(2) 0.0269(8) Uani 1 1 d . . . . .
H23 H 0.619466 -0.487861 0.229717 0.040 Uiso 1 1 calc R U . . .
H24 H 0.749370 -0.352024 0.225180 0.040 Uiso 1 1 calc R U . . .
H25 H 0.584316 -0.442123 0.149574 0.040 Uiso 1 1 calc R U . . .
C12 C 0.3013(4) -0.4405(3) 0.2885(2) 0.0251(8) Uani 1 1 d . . . . .
H26 H 0.235976 -0.497545 0.228647 0.038 Uiso 1 1 calc R U . . .
H27 H 0.232288 -0.393706 0.324345 0.038 Uiso 1 1 calc R U . . .
H28 H 0.330400 -0.496535 0.316932 0.038 Uiso 1 1 calc R U . . .
C13 C 0.6158(5) -0.2325(3) 0.3991(2) 0.0288(9) Uani 1 1 d . . . . .
H29 H 0.638152 -0.300446 0.417757 0.043 Uiso 1 1 calc R U . . .
H30 H 0.543878 -0.193131 0.437693 0.043 Uiso 1 1 calc R U . . .
H31 H 0.724477 -0.161714 0.403867 0.043 Uiso 1 1 calc R U . . .
Si4 Si 0.27979(11) -0.29136(7) 0.13395(5) 0.0166(2) Uani 1 1 d . . . . .
C14 C 0.0781(4) -0.3190(3) 0.1833(2) 0.0241(8) Uani 1 1 d . . . . .
H32 H 0.055807 -0.234503 0.205918 0.036 Uiso 1 1 calc R U . . .
H33 H 0.090897 -0.349101 0.232417 0.036 Uiso 1 1 calc R U . . .
H34 H -0.017756 -0.387671 0.137408 0.036 Uiso 1 1 calc R U . . .
C15 C 0.2398(5) -0.2156(3) 0.0523(2) 0.0266(8) Uani 1 1 d . . . . .
H35 H 0.122643 -0.264491 0.019538 0.040 Uiso 1 1 calc R U . . .
H36 H 0.320818 -0.221694 0.010249 0.040 Uiso 1 1 calc R U . . .
H37 H 0.254893 -0.120855 0.084414 0.040 Uiso 1 1 calc R U . . .
C16 C 0.2809(5) -0.4614(3) 0.0613(2) 0.0266(8) Uani 1 1 d . . . . .
H38 H 0.177711 -0.508434 0.015806 0.040 Uiso 1 1 calc R U . . .
H39 H 0.283291 -0.514270 0.098020 0.040 Uiso 1 1 calc R U . . .
H40 H 0.382388 -0.449969 0.032196 0.040 Uiso 1 1 calc R U . . .
C17 C 0.7502(4) -0.0729(3) 0.12120(19) 0.0166(7) Uani 1 1 d . . . . .
C18 C 0.7169(5) -0.2178(3) 0.0569(2) 0.0229(8) Uani 1 1 d . . . . .
H41 H 0.593550 -0.268559 0.042436 0.034 Uiso 1 1 calc R U . . .
H42 H 0.773990 -0.260884 0.085254 0.034 Uiso 1 1 calc R U . . .
H43 H 0.761930 -0.216183 0.002123 0.034 Uiso 1 1 calc R U . . .
C19 C 0.6599(5) -0.0079(3) 0.0762(2) 0.0233(8) Uani 1 1 d . . . . .
H44 H 0.697454 0.088875 0.111249 0.035 Uiso 1 1 calc R U . . .
H45 H 0.535911 -0.048529 0.072136 0.035 Uiso 1 1 calc R U . . .
H46 H 0.688084 -0.022279 0.016098 0.035 Uiso 1 1 calc R U . . .
C20 C 0.9430(4) 0.0043(3) 0.1395(2) 0.0221(7) Uani 1 1 d . . . . .
H47 H 0.981662 0.009338 0.083947 0.033 Uiso 1 1 calc R U . . .
H48 H 1.002578 -0.042505 0.162803 0.033 Uiso 1 1 calc R U . . .
H49 H 0.968442 0.095440 0.183404 0.033 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 0.0033 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'
Si Si 0.0817 0.0704 '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
C17 P1 C4 116.13(12) . . ?
C17 P1 C1 111.33(12) . . ?
C4 P1 C1 98.02(13) . . ?
C2 C1 P1 98.58(17) . . ?
C2 C1 Si1 105.71(19) . . ?
P1 C1 Si1 127.49(15) . . ?
C2 C1 Si2 107.69(18) . . ?
P1 C1 Si2 106.64(14) . . ?
Si1 C1 Si2 108.99(13) . . ?
C3 C2 C1 111.1(2) . . ?
C2 C3 C4 110.4(3) . . ?
C3 C4 P1 103.00(18) . . ?
C3 C4 Si4 105.47(19) . . ?
P1 C4 Si4 129.76(16) . . ?
C3 C4 Si3 110.6(2) . . ?
P1 C4 Si3 101.08(13) . . ?
Si4 C4 Si3 106.33(13) . . ?
C7 Si1 C6 107.40(16) . . ?
C7 Si1 C5 103.41(16) . . ?
C6 Si1 C5 104.46(16) . . ?
C7 Si1 C1 114.83(13) . . ?
C6 Si1 C1 117.09(15) . . ?
C5 Si1 C1 108.30(14) . . ?
C10 Si2 C8 107.01(15) . . ?
C10 Si2 C9 103.30(16) . . ?
C8 Si2 C9 106.49(16) . . ?
C10 Si2 C1 114.72(12) . . ?
C8 Si2 C1 109.94(16) . . ?
C9 Si2 C1 114.73(13) . . ?
C11 Si3 C12 106.90(15) . . ?
C11 Si3 C13 107.32(16) . . ?
C12 Si3 C13 101.53(16) . . ?
C11 Si3 C4 111.59(14) . . ?
C12 Si3 C4 114.76(14) . . ?
C13 Si3 C4 113.95(13) . . ?
C15 Si4 C14 102.79(15) . . ?
C15 Si4 C16 103.82(15) . . ?
C14 Si4 C16 107.59(15) . . ?
C15 Si4 C4 119.09(13) . . ?
C14 Si4 C4 107.26(14) . . ?
C16 Si4 C4 115.17(13) . . ?
C19 C17 C20 109.2(2) . . ?
C19 C17 C18 108.7(2) . . ?
C20 C17 C18 107.9(3) . . ?
C19 C17 P1 120.0(2) . . ?
C20 C17 P1 104.50(19) . . ?
C18 C17 P1 106.1(2) . . ?
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 C17 1.891(3) . ?
P1 C4 1.910(3) . ?
P1 C1 1.912(3) . ?
C1 C2 1.574(5) . ?
C1 Si1 1.927(3) . ?
C1 Si2 1.939(3) . ?
C2 C3 1.526(4) . ?
C3 C4 1.567(4) . ?
C4 Si4 1.921(3) . ?
C4 Si3 1.932(3) . ?
Si1 C7 1.883(3) . ?
Si1 C6 1.886(4) . ?
Si1 C5 1.887(3) . ?
Si2 C10 1.865(3) . ?
Si2 C8 1.877(3) . ?
Si2 C9 1.879(4) . ?
Si3 C11 1.872(3) . ?
Si3 C12 1.875(4) . ?
Si3 C13 1.882(3) . ?
Si4 C15 1.875(3) . ?
Si4 C14 1.876(4) . ?
Si4 C16 1.883(3) . ?
C17 C19 1.523(4) . ?
C17 C20 1.529(5) . ?
C17 C18 1.537(4) . ?
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
P1 C1 C2 C3 -42.8(2) . . . . ?
Si1 C1 C2 C3 90.2(2) . . . . ?
Si2 C1 C2 C3 -153.41(18) . . . . ?
C1 C2 C3 C4 46.8(3) . . . . ?
C2 C3 C4 P1 -23.7(3) . . . . ?
C2 C3 C4 Si4 -161.9(2) . . . . ?
C2 C3 C4 Si3 83.6(3) . . . . ?
C4 P1 C17 C19 62.1(2) . . . . ?
C1 P1 C17 C19 -48.9(3) . . . . ?
C4 P1 C17 C20 -175.19(16) . . . . ?
C1 P1 C17 C20 73.8(2) . . . . ?
C4 P1 C17 C18 -61.3(2) . . . . ?
C1 P1 C17 C18 -172.33(19) . . . . ?
