#------------------------------------------------------------------------------
#$Date: 2020-08-08 02:15:15 +0300 (Sat, 08 Aug 2020) $
#$Revision: 255188 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/86/4038658.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_4038658
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            'C17 H43 P Si4'
_chemical_formula_weight         390.84
_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                105.432(2)
_cell_angle_beta                 100.772(2)
_cell_angle_gamma                112.646(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1062(15)
_cell_length_b                   11.3846(18)
_cell_length_c                   13.688(2)
_cell_measurement_reflns_used    4906
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      2.45
_cell_volume                     1193.8(3)
_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 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0232
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5633
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.089
_exptl_absorpt_coefficient_mu    0.314
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3660
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.087
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.793
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         4097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0377
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1301
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3746
_reflns_number_total             4097
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01393_si_003.cif
_cod_data_source_block           fh28aa_CCDC-1991933
_cod_database_code               4038658
_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   0.885
_shelx_estimated_absorpt_t_max   0.940
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
Si2 Si 0.38487(5) 0.49305(4) 0.68004(4) 0.01891(16) Uani 1 1 d . . . . .
Si4 Si 0.36112(5) 0.06162(4) 0.70456(4) 0.02053(17) Uani 1 1 d . . . . .
Si3 Si 0.15058(5) 0.08221(4) 0.86143(4) 0.02207(17) Uani 1 1 d . . . . .
P1 P 0.15068(5) 0.20975(3) 0.67274(3) 0.01791(16) Uani 1 1 d . . . . .
Si1 Si 0.09398(5) 0.47669(4) 0.77367(4) 0.01936(16) Uani 1 1 d . . . . .
C1 C 0.24549(18) 0.40083(13) 0.75313(12) 0.0158(3) Uani 1 1 d . . . . .
C4 C 0.26738(18) 0.16842(14) 0.77799(13) 0.0172(3) Uani 1 1 d . . . . .
C2 C 0.35372(18) 0.42232(14) 0.86539(12) 0.0170(3) Uani 1 1 d . . . . .
H1 H 0.451446 0.514826 0.896970 0.020 Uiso 1 1 calc R U . . .
H2 H 0.285400 0.415628 0.913969 0.020 Uiso 1 1 calc R U . . .
C3 C 0.41552(17) 0.31270(13) 0.85380(12) 0.0165(3) Uani 1 1 d . . . . .
H3 H 0.457985 0.310720 0.925109 0.020 Uiso 1 1 calc R U . . .
H4 H 0.509049 0.335679 0.823728 0.020 Uiso 1 1 calc R U . . .
C17 C 0.4570(2) 0.13224(17) 0.61034(15) 0.0321(4) Uani 1 1 d . . . . .
H5 H 0.488053 0.067561 0.567337 0.048 Uiso 1 1 calc R U . . .
H6 H 0.557729 0.220188 0.651475 0.048 Uiso 1 1 calc R U . . .
H7 H 0.375476 0.145948 0.562897 0.048 Uiso 1 1 calc R U . . .
C11 C 0.60288(19) 0.51191(16) 0.72145(14) 0.0238(4) Uani 1 1 d . . . . .
H8 H 0.599782 0.422124 0.692596 0.036 Uiso 1 1 calc R U . . .
H9 H 0.648988 0.548576 0.799846 0.036 Uiso 1 1 calc R U . . .
H10 H 0.674142 0.574911 0.693601 0.036 Uiso 1 1 calc R U . . .
C8 C -0.0220(2) 0.47620(19) 0.64500(15) 0.0308(4) Uani 1 1 d . . . . .
H11 H -0.096394 0.381348 0.595414 0.046 Uiso 1 1 calc R U . . .
H12 H 0.058895 0.522621 0.612887 0.046 Uiso 1 1 calc R U . . .
H13 H -0.089234 0.524376 0.659432 0.046 Uiso 1 1 calc R U . . .
C6 C -0.0683(2) 0.39545(18) 0.83351(15) 0.0303(4) Uani 1 1 d . . . . .
H14 H -0.013745 0.386856 0.898246 0.045 Uiso 1 1 calc R U . . .
H15 H -0.152020 0.304280 0.781458 0.045 Uiso 1 1 calc R U . . .
H16 H -0.123841 0.452739 0.852108 0.045 Uiso 1 1 calc R U . . .
C16 C 0.5389(2) 0.05926(17) 0.79817(15) 0.0313(4) Uani 1 1 d . . . . .
H17 H 0.493416 -0.000454 0.836378 0.047 Uiso 1 1 calc R U . . .
H18 H 0.615305 0.152518 0.849990 0.047 Uiso 1 1 calc R U . . .
H19 H 0.600439 0.024498 0.756916 0.047 Uiso 1 1 calc R U . . .
C10 C 0.2882(2) 0.40313(19) 0.53090(14) 0.0339(5) Uani 1 1 d . . . . .
H20 H 0.339898 0.465727 0.496198 0.051 Uiso 1 1 calc R U . . .
H21 H 0.167016 0.374185 0.510399 0.051 Uiso 1 1 calc R U . . .
H22 H 0.307203 0.322472 0.508124 0.051 Uiso 1 1 calc R U . . .
C14 C 0.2902(2) 0.0403(2) 0.94990(17) 0.0394(5) Uani 1 1 d . . . . .
H23 H 0.404741 0.116277 0.979466 0.059 Uiso 1 1 calc R U . . .
H24 H 0.291557 -0.043497 0.907910 0.059 Uiso 1 1 calc R U . . .
H25 H 0.247491 0.026244 1.008608 0.059 Uiso 1 1 calc R U . . .
C5 C -0.0719(2) 0.12704(17) 0.66343(15) 0.0302(4) Uani 1 1 d . . . . .
H26 H -0.120903 0.028134 0.623419 0.045 Uiso 1 1 calc R U . . .
H27 H -0.132936 0.165519 0.626257 0.045 Uiso 1 1 calc R U . . .
H28 H -0.080458 0.143367 0.735665 0.045 Uiso 1 1 calc R U . . .
C15 C 0.1972(2) -0.11929(15) 0.62283(15) 0.0316(4) Uani 1 1 d . . . . .
H29 H 0.245930 -0.168083 0.580212 0.047 Uiso 1 1 calc R U . . .
H30 H 0.102745 -0.119154 0.574906 0.047 Uiso 1 1 calc R U . . .
H31 H 0.156984 -0.165356 0.670593 0.047 Uiso 1 1 calc R U . . .
C12 C 0.0959(2) 0.19573(18) 0.95834(15) 0.0351(5) Uani 1 1 d . . . . .
H32 H 0.039567 0.146241 0.999874 0.053 Uiso 1 1 calc R U . . .
H33 H 0.020498 0.222137 0.918830 0.053 Uiso 1 1 calc R U . . .
H34 H 0.198854 0.278185 1.007004 0.053 Uiso 1 1 calc R U . . .
C13 C -0.0490(2) -0.08285(18) 0.78202(17) 0.0381(5) Uani 1 1 d . . . . .
H35 H -0.055867 -0.112977 0.706518 0.057 Uiso 1 1 calc R U . . .
H36 H -0.146392 -0.067809 0.788264 0.057 Uiso 1 1 calc R U . . .
H37 H -0.048447 -0.153488 0.810035 0.057 Uiso 1 1 calc R U . . .
C7 C 0.2129(2) 0.65519(17) 0.87837(17) 0.0376(5) Uani 1 1 d . . . . .
H38 H 0.136295 0.695821 0.885379 0.056 Uiso 1 1 calc R U . . .
H39 H 0.303909 0.711256 0.857091 0.056 Uiso 1 1 calc R U . . .
H40 H 0.260659 0.651571 0.947233 0.056 Uiso 1 1 calc R U . . .
C9 C 0.4307(2) 0.67734(17) 0.7101(2) 0.0407(5) Uani 1 1 d . . . . .
H41 H 0.494083 0.731135 0.786405 0.061 Uiso 1 1 calc R U . . .
H42 H 0.324602 0.682618 0.692599 0.061 Uiso 1 1 calc R U . . .
H43 H 0.497277 0.714171 0.667060 0.061 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
C11 Si2 C10 109.11(8) . . ?
C11 Si2 C9 100.85(8) . . ?
C10 Si2 C9 106.48(10) . . ?
C11 Si2 C1 112.95(7) . . ?
C10 Si2 C1 111.48(7) . . ?
C9 Si2 C1 115.25(8) . . ?
C15 Si4 C17 106.70(9) . . ?
C15 Si4 C16 108.83(8) . . ?
C17 Si4 C16 104.05(9) . . ?
C15 Si4 C4 111.50(8) . . ?
C17 Si4 C4 112.51(7) . . ?
C16 Si4 C4 112.80(8) . . ?
C12 Si3 C14 103.49(10) . . ?
C12 Si3 C13 107.02(9) . . ?
C14 Si3 C13 106.56(9) . . ?
C12 Si3 C4 113.77(7) . . ?
C14 Si3 C4 109.84(8) . . ?
C13 Si3 C4 115.28(8) . . ?
C5 P1 C4 105.97(7) . . ?
C5 P1 C1 109.05(8) . . ?
C4 P1 C1 96.39(6) . . ?
C6 Si1 C8 106.76(8) . . ?
C6 Si1 C7 100.22(9) . . ?
C8 Si1 C7 110.91(9) . . ?
C6 Si1 C1 117.21(7) . . ?
C8 Si1 C1 111.46(8) . . ?
C7 Si1 C1 109.73(8) . . ?
C2 C1 P1 104.74(9) . . ?
C2 C1 Si1 108.35(11) . . ?
P1 C1 Si1 117.66(7) . . ?
C2 C1 Si2 111.24(10) . . ?
P1 C1 Si2 106.45(8) . . ?
Si1 C1 Si2 108.37(6) . . ?
C3 C4 P1 102.80(8) . . ?
C3 C4 Si3 109.29(11) . . ?
P1 C4 Si3 119.15(8) . . ?
C3 C4 Si4 108.08(10) . . ?
P1 C4 Si4 105.82(8) . . ?
Si3 C4 Si4 110.98(7) . . ?
C3 C2 C1 109.80(12) . . ?
C2 C3 C4 109.83(11) . . ?
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
Si2 C11 1.8694(16) . ?
Si2 C10 1.8742(19) . ?
Si2 C9 1.8834(17) . ?
Si2 C1 1.9292(16) . ?
Si4 C15 1.8719(16) . ?
Si4 C17 1.8720(19) . ?
Si4 C16 1.8812(17) . ?
Si4 C4 1.9201(17) . ?
Si3 C12 1.873(2) . ?
Si3 C14 1.8737(17) . ?
Si3 C13 1.8869(18) . ?
Si3 C4 1.9094(16) . ?
P1 C5 1.8387(17) . ?
P1 C4 1.8973(15) . ?
P1 C1 1.9008(15) . ?
Si1 C6 1.8740(18) . ?
Si1 C8 1.8742(17) . ?
Si1 C7 1.8792(18) . ?
Si1 C1 1.9135(16) . ?
C1 C2 1.5622(19) . ?
C4 C3 1.5678(19) . ?
C2 C3 1.5389(19) . ?
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
C5 P1 C4 C3 -129.68(11) . . . . ?
C1 P1 C4 C3 -17.73(11) . . . . ?
C5 P1 C4 Si3 -8.70(11) . . . . ?
C1 P1 C4 Si3 103.24(9) . . . . ?
C5 P1 C4 Si4 117.05(8) . . . . ?
C1 P1 C4 Si4 -131.00(7) . . . . ?
P1 C1 C2 C3 28.23(14) . . . . ?
Si1 C1 C2 C3 154.60(10) . . . . ?
Si2 C1 C2 C3 -86.38(12) . . . . ?
C1 C2 C3 C4 -44.76(16) . . . . ?
P1 C4 C3 C2 37.42(14) . . . . ?
Si3 C4 C3 C2 -90.08(12) . . . . ?
Si4 C4 C3 C2 149.03(11) . . . . ?
