#------------------------------------------------------------------------------
#$Date: 2020-08-08 02:15:15 +0300 (Sat, 08 Aug 2020) $
#$Revision: 255188 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/86/4038660.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_4038660
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            'C19 H47 P Si4'
_chemical_formula_weight         418.89
_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   mixed
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                106.972(2)
_cell_angle_beta                 91.957(3)
_cell_angle_gamma                109.448(2)
_cell_formula_units_Z            2
_cell_length_a                   8.501(2)
_cell_length_b                   11.132(3)
_cell_length_c                   15.430(4)
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.84
_cell_measurement_theta_min      2.57
_cell_volume                     1302.9(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 0.995
_diffrn_measured_fraction_theta_max 0.993
_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  0.0249
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_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       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13244
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         2.049
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5931
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.068
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5082
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0317
_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)+(0.0370P)²+0.5260P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0833
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4641
_reflns_number_total             5082
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01393_si_003.cif
_cod_data_source_block           fh74aa_CCDC-1991935
_cod_original_cell_volume        1302.8(5)
_cod_database_code               4038660
_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   0.944
_shelx_estimated_absorpt_t_max   0.944
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
Si1 Si 0.17869(5) 0.25681(4) 0.78896(3) 0.02560(11) Uani 1 1 d . . . . .
Si2 Si 0.42060(5) 0.16622(4) 0.89164(3) 0.02493(11) Uani 1 1 d . . . . .
Si3 Si -0.19434(5) -0.24818(4) 0.62198(3) 0.02816(11) Uani 1 1 d . . . . .
Si4 Si 0.01366(5) -0.28982(4) 0.77463(3) 0.02557(11) Uani 1 1 d . . . . .
P1 P 0.14193(7) -0.02061(6) 0.69167(4) 0.01583(19) Uani 0.5773(14) 1 d . . P A
1
C1 C 0.21089(18) 0.10702(13) 0.81318(9) 0.0222(3) Uani 1 1 d . . . . .
C2 C 0.0627(2) 0.04852(14) 0.86511(10) 0.0268(3) Uani 1 1 d . . . . .
H1 H 0.103597 0.012973 0.909486 0.032 Uiso 1 1 calc R U . . .
H2 H 0.024677 0.121374 0.899685 0.032 Uiso 1 1 calc R U . . .
C3 C -0.08532(18) -0.06371(14) 0.79781(10) 0.0237(3) Uani 1 1 d . . . . .
H3 H -0.148528 -0.024283 0.766382 0.028 Uiso 1 1 calc R U . . .
H4 H -0.162917 -0.115347 0.831457 0.028 Uiso 1 1 calc R U . . .
C4 C -0.01970(17) -0.16003(13) 0.72534(9) 0.0211(3) Uani 1 1 d . . . . .
P2 P 0.21601(10) -0.06040(8) 0.72968(5) 0.0155(3) Uani 0.4227(14) 1 d . . P A 2
C5 C 0.3186(3) -0.0774(2) 0.65442(16) 0.0196(5) Uani 0.5773(14) 1 d . . P A 1
H5 H 0.364857 -0.108380 0.700720 0.024 Uiso 0.5773(14) 1 calc R U P A 1
C6 C 0.4548(2) 0.04812(18) 0.63848(12) 0.0351(4) Uani 1 1 d . . . . .
H51 H 0.541(3) 0.010(2) 0.6287(15) 0.057(6) Uiso 1 1 d . . . . .
H49 H 0.492(3) 0.125(2) 0.6927(15) 0.050(6) Uiso 1 1 d . . . . .
C7 C 0.2534(5) -0.1879(4) 0.5616(2) 0.0261(7) Uani 0.5773(14) 1 d . . P A 1
H6 H 0.347052 -0.212523 0.536836 0.039 Uiso 0.5773(14) 1 calc R U P A 1
H7 H 0.203893 -0.155044 0.519274 0.039 Uiso 0.5773(14) 1 calc R U P A 1
H8 H 0.167411 -0.266959 0.569198 0.039 Uiso 0.5773(14) 1 calc R U P A 1
C8 C 0.2564(4) -0.0258(3) 0.6199(2) 0.0200(7) Uani 0.4227(14) 1 d . . P A 2
H9 H 0.195155 0.030755 0.606189 0.024 Uiso 0.4227(14) 1 calc R U P A 2
C9 C 0.2226(7) -0.1570(5) 0.5411(4) 0.0286(11) Uani 0.4227(14) 1 d . . P A 2
H10 H 0.280941 -0.210335 0.559308 0.043 Uiso 0.4227(14) 1 calc R U P A 2
H11 H 0.264229 -0.136006 0.486880 0.043 Uiso 0.4227(14) 1 calc R U P A 2
H12 H 0.101111 -0.208506 0.526952 0.043 Uiso 0.4227(14) 1 calc R U P A 2
C10 C -0.0406(2) 0.21878(19) 0.73485(15) 0.0447(4) Uani 1 1 d . . . . .
H13 H -0.065525 0.148706 0.675088 0.067 Uiso 1 1 calc R U . . .
H14 H -0.049625 0.300441 0.726717 0.067 Uiso 1 1 calc R U . . .
H15 H -0.121304 0.187316 0.774458 0.067 Uiso 1 1 calc R U . . .
C11 C 0.3221(2) 0.32863(15) 0.71304(11) 0.0288(3) Uani 1 1 d . . . . .
H16 H 0.299400 0.405990 0.705482 0.043 Uiso 1 1 calc R U . . .
H17 H 0.302512 0.259923 0.653073 0.043 Uiso 1 1 calc R U . . .
H18 H 0.439612 0.357623 0.740766 0.043 Uiso 1 1 calc R U . . .
C12 C 0.2079(2) 0.39532(16) 0.89957(12) 0.0368(4) Uani 1 1 d . . . . .
H19 H 0.184165 0.469372 0.886919 0.055 Uiso 1 1 calc R U . . .
H20 H 0.324365 0.428039 0.929892 0.055 Uiso 1 1 calc R U . . .
H21 H 0.130423 0.360786 0.939576 0.055 Uiso 1 1 calc R U . . .
C13 C 0.5920(2) 0.31596(16) 0.87924(11) 0.0312(3) Uani 1 1 d . . . . .
H22 H 0.619626 0.294086 0.816757 0.047 Uiso 1 1 calc R U . . .
H23 H 0.692532 0.339730 0.922930 0.047 Uiso 1 1 calc R U . . .
H24 H 0.553362 0.392207 0.891575 0.047 Uiso 1 1 calc R U . . .
C14 C 0.3842(2) 0.21698(18) 1.01422(11) 0.0360(4) Uani 1 1 d . . . . .
H25 H 0.492999 0.261256 1.054355 0.054 Uiso 1 1 calc R U . . .
H26 H 0.317694 0.136875 1.029102 0.054 Uiso 1 1 calc R U . . .
H27 H 0.323045 0.279311 1.023199 0.054 Uiso 1 1 calc R U . . .
C15 C 0.5246(2) 0.03871(18) 0.87802(13) 0.0381(4) Uani 1 1 d . . . . .
H28 H 0.613174 0.068856 0.930219 0.057 Uiso 1 1 calc R U . . .
H29 H 0.574548 0.028594 0.821228 0.057 Uiso 1 1 calc R U . . .
H30 H 0.440527 -0.047956 0.875512 0.057 Uiso 1 1 calc R U . . .
C16 C -0.2014(3) -0.1393(2) 0.55114(12) 0.0434(4) Uani 1 1 d . . . . .
H31 H -0.301365 -0.185559 0.504191 0.065 Uiso 1 1 calc R U . . .
H32 H -0.099788 -0.120768 0.521585 0.065 Uiso 1 1 calc R U . . .
H33 H -0.206908 -0.054352 0.590466 0.065 Uiso 1 1 calc R U . . .
C17 C -0.1875(2) -0.40867(17) 0.54129(12) 0.0418(4) Uani 1 1 d . . . . .
H34 H -0.082798 -0.389518 0.514355 0.063 Uiso 1 1 calc R U . . .
H35 H -0.284294 -0.448501 0.492509 0.063 Uiso 1 1 calc R U . . .
H36 H -0.191709 -0.471809 0.574849 0.063 Uiso 1 1 calc R U . . .
C18 C -0.4059(2) -0.29064(19) 0.66232(13) 0.0415(4) Uani 1 1 d . . . . .
H37 H -0.495005 -0.333086 0.609299 0.062 Uiso 1 1 calc R U . . .
H38 H -0.417766 -0.208159 0.701464 0.062 Uiso 1 1 calc R U . . .
H39 H -0.415197 -0.352838 0.697253 0.062 Uiso 1 1 calc R U . . .
C19 C 0.1480(2) -0.37844(19) 0.71227(14) 0.0419(4) Uani 1 1 d . . . . .
H40 H 0.148805 -0.450237 0.736710 0.063 Uiso 1 1 calc R U . . .
H41 H 0.263364 -0.314259 0.720378 0.063 Uiso 1 1 calc R U . . .
H42 H 0.102543 -0.417424 0.646929 0.063 Uiso 1 1 calc R U . . .
C20 C -0.1914(2) -0.42321(17) 0.77444(13) 0.0400(4) Uani 1 1 d . . . . .
H43 H -0.170453 -0.482900 0.805437 0.060 Uiso 1 1 calc R U . . .
H44 H -0.244561 -0.475617 0.711133 0.060 Uiso 1 1 calc R U . . .
H45 H -0.266335 -0.380827 0.806662 0.060 Uiso 1 1 calc R U . . .
C21 C 0.1046(2) -0.22200(19) 0.89877(12) 0.0399(4) Uani 1 1 d . . . . .
H46 H 0.212077 -0.147379 0.908313 0.060 Uiso 1 1 calc R U . . .
H47 H 0.123425 -0.293372 0.917778 0.060 Uiso 1 1 calc R U . . .
H48 H 0.025931 -0.189732 0.935227 0.060 Uiso 1 1 calc R U . . .
H50 H 0.441(3) 0.075(2) 0.5871(16) 0.057(6) Uiso 1 1 d . . . . .
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 Si1 C10 105.81(8) . . ?
C11 Si1 C12 108.04(8) . . ?
C10 Si1 C12 103.90(9) . . ?
C11 Si1 C1 114.73(7) . . ?
C10 Si1 C1 113.72(7) . . ?
C12 Si1 C1 109.93(7) . . ?
C15 Si2 C14 106.95(8) . . ?
C15 Si2 C13 103.14(8) . . ?
C14 Si2 C13 105.76(8) . . ?
C15 Si2 C1 115.58(8) . . ?
C14 Si2 C1 109.08(7) . . ?
C13 Si2 C1 115.56(7) . . ?
C16 Si3 C17 106.54(9) . . ?
C16 Si3 C18 104.29(9) . . ?
C17 Si3 C18 106.84(9) . . ?
C16 Si3 C4 113.33(8) . . ?
C17 Si3 C4 115.38(7) . . ?
C18 Si3 C4 109.69(7) . . ?
C19 Si4 C21 107.06(9) . . ?
C19 Si4 C20 106.73(9) . . ?
C21 Si4 C20 101.65(8) . . ?
C19 Si4 C4 114.09(7) . . ?
C21 Si4 C4 114.60(7) . . ?
C20 Si4 C4 111.71(7) . . ?
C5 P1 C4 108.20(9) . . ?
C5 P1 C1 109.31(9) . . ?
C4 P1 C1 95.81(6) . . ?
C2 C1 Si1 106.79(10) . . ?
C2 C1 Si2 108.58(10) . . ?
Si1 C1 Si2 109.99(7) . . ?
C2 C1 P1 102.41(9) . . ?
Si1 C1 P1 99.07(7) . . ?
Si2 C1 P1 128.15(8) . . ?
C2 C1 P2 99.61(9) . . ?
Si1 C1 P2 130.54(8) . . ?
Si2 C1 P2 99.72(7) . . ?
C3 C2 C1 110.82(11) . . ?
C2 C3 C4 110.10(12) . . ?
C3 C4 Si4 109.32(10) . . ?
C3 C4 Si3 105.76(10) . . ?
Si4 C4 Si3 109.80(7) . . ?
C3 C4 P1 95.59(9) . . ?
Si4 C4 P1 129.55(8) . . ?
Si3 C4 P1 104.15(7) . . ?
C3 C4 P2 105.78(9) . . ?
Si4 C4 P2 96.16(7) . . ?
Si3 C4 P2 128.92(8) . . ?
C8 P2 C4 110.78(12) . . ?
C8 P2 C1 104.82(11) . . ?
C4 P2 C1 94.54(7) . . ?
C7 C5 C6 107.6(2) . . ?
C7 C5 P1 107.59(19) . . ?
C6 C5 P1 105.14(14) . . ?
C9 C8 C6 105.5(3) . . ?
C9 C8 P2 110.8(3) . . ?
C6 C8 P2 101.11(18) . . ?
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
Si1 C11 1.8690(16) . ?
Si1 C10 1.8743(19) . ?
Si1 C12 1.8792(17) . ?
Si1 C1 1.9120(15) . ?
Si2 C15 1.8748(17) . ?
Si2 C14 1.8775(17) . ?
Si2 C13 1.8778(17) . ?
Si2 C1 1.9190(16) . ?
Si3 C16 1.8671(19) . ?
Si3 C17 1.8766(17) . ?
Si3 C18 1.8778(18) . ?
Si3 C4 1.9143(15) . ?
Si4 C19 1.8642(16) . ?
Si4 C21 1.8716(18) . ?
Si4 C20 1.8754(18) . ?
Si4 C4 1.9094(15) . ?
P1 C5 1.861(2) . ?
P1 C4 1.9146(15) . ?
P1 C1 1.9216(15) . ?
C1 C2 1.5751(19) . ?
C1 P2 1.9471(16) . ?
C2 C3 1.526(2) . ?
C3 C4 1.5660(17) . ?
C4 P2 1.9279(17) . ?
P2 C8 1.862(3) . ?
C5 C7 1.528(4) . ?
C5 C6 1.580(3) . ?
C6 C8 1.584(4) . ?
C8 C9 1.534(6) . ?
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
Si1 C1 C2 C3 92.71(12) . . . . ?
Si2 C1 C2 C3 -148.72(10) . . . . ?
P1 C1 C2 C3 -10.88(14) . . . . ?
P2 C1 C2 C3 -44.98(13) . . . . ?
C1 C2 C3 C4 44.06(16) . . . . ?
C2 C3 C4 Si4 83.83(12) . . . . ?
C2 C3 C4 Si3 -158.01(10) . . . . ?
C2 C3 C4 P1 -51.58(12) . . . . ?
C2 C3 C4 P2 -18.71(14) . . . . ?
C4 P1 C5 C7 71.6(2) . . . . ?
C1 P1 C5 C7 174.83(19) . . . . ?
C4 P1 C5 C6 -173.92(12) . . . . ?
C1 P1 C5 C6 -70.73(15) . . . . ?
C4 P2 C8 C9 -65.7(3) . . . . ?
C1 P2 C8 C9 -166.6(3) . . . . ?
C4 P2 C8 C6 -177.17(13) . . . . ?
C1 P2 C8 C6 82.00(17) . . . . ?
