#------------------------------------------------------------------------------
#$Date: 2016-03-23 14:48:36 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179307 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/04/4320417.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_4320417
loop_
_publ_author_name
'Jun Ho Shin'
'Brian M. Bridgewater'
'David G. Churchill'
'Gerard Parkin'
_publ_section_title
;
 Synthesis and Structural Characterization of PhP[(C5Me4)2], a Monodentate
 Chiral Phosphine Derived from Intramolecular C-C Coupling of
 Tetramethylcyclopentadienyl Groups: An Evaluation of Steric and
 Electronic Properties
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5626
_journal_page_last               5635
_journal_paper_doi               10.1021/ic010443j
_journal_volume                  40
_journal_year                    2001
_chemical_formula_sum            'C12 H17 P S'
_chemical_formula_weight         224.29
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                75.803(4)
_cell_angle_beta                 84.522(3)
_cell_angle_gamma                83.910(4)
_cell_formula_units_Z            2
_cell_length_a                   7.1664(13)
_cell_length_b                   9.0998(16)
_cell_length_c                   10.080(2)
_cell_measurement_temperature    233(2)
_cell_volume                     632.0(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      233(2)
_diffrn_measured_fraction_theta_full 0.869
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0632
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4383
_diffrn_reflns_theta_full        28.24
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.345
_exptl_absorpt_correction_T_max  0.9342
_exptl_absorpt_correction_T_min  0.9342
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(13)
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3357
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.456
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0496P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1050
_reflns_number_gt                2487
_reflns_number_total             3357
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic010443j_07.cif
_cod_data_source_block           ds10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        632.1(2)
_cod_database_code               4320417
loop_
_symmetry_equiv_pos_as_xyz
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P -0.29601(16) -0.10347(12) 1.77282(13) 0.0373(3) Uani 1 1 d . . .
S1 S -0.3578(2) 0.10415(14) 1.66831(16) 0.0600(5) Uani 1 1 d . . .
C1 C -0.5527(9) -0.0441(8) 1.9863(8) 0.091(2) Uani 1 1 d . . .
H1A H -0.5087 0.0565 1.9696 0.136 Uiso 1 1 calc R . .
H1B H -0.5947 -0.0778 2.0824 0.136 Uiso 1 1 calc R . .
H1C H -0.6565 -0.0404 1.9301 0.136 Uiso 1 1 calc R . .
C2 C -0.3954(7) -0.1531(6) 1.9504(5) 0.0484(13) Uani 1 1 d . . .
H2A H -0.4455 -0.2537 1.9659 0.058 Uiso 1 1 calc R . .
C3 C -0.2242(9) -0.1738(8) 2.0347(6) 0.0753(19) Uani 1 1 d . . .
H3A H -0.1955 -0.0753 2.0470 0.090 Uiso 1 1 calc R . .
H3B H -0.2501 -0.2407 2.1255 0.090 Uiso 1 1 calc R . .
C4 C -0.0593(9) -0.2432(8) 1.9591(6) 0.0661(16) Uani 1 1 d . . .
H4A H -0.0778 -0.3488 1.9606 0.079 Uiso 1 1 calc R . .
H4B H 0.0574 -0.2420 2.0021 0.079 Uiso 1 1 calc R . .
C5 C -0.0493(7) -0.1476(6) 1.8129(5) 0.0499(14) Uani 1 1 d . . .
H5A H 0.0008 -0.0508 1.8142 0.060 Uiso 1 1 calc R . .
C6 C 0.0785(8) -0.2183(7) 1.7111(7) 0.0716(18) Uani 1 1 d . . .
H6A H 0.0460 -0.3209 1.7181 0.107 Uiso 1 1 calc R . .
H6B H 0.2085 -0.2215 1.7318 0.107 Uiso 1 1 calc R . .
H6C H 0.0623 -0.1576 1.6187 0.107 Uiso 1 1 calc R . .
C21 C -0.3530(6) -0.2473(5) 1.6895(5) 0.0365(11) Uani 1 1 d . . .
C22 C -0.3664(6) -0.3968(5) 1.7579(5) 0.0434(12) Uani 1 1 d . . .
H22A H -0.3511 -0.4262 1.8526 0.052 Uiso 1 1 calc R . .
C23 C -0.4020(7) -0.5047(6) 1.6903(6) 0.0535(14) Uani 1 1 d . . .
H23A H -0.4145 -0.6059 1.7389 0.064 Uiso 1 1 calc R . .
C24 C -0.4188(7) -0.4621(7) 1.5509(6) 0.0545(15) Uani 1 1 d . . .
H24A H -0.4399 -0.5353 1.5038 0.065 Uiso 1 1 calc R . .
C25 C -0.4051(8) -0.3145(7) 1.4805(7) 0.0554(13) Uani 1 1 d . . .
H25A H -0.4179 -0.2869 1.3855 0.066 Uiso 1 1 calc R . .
C26 C -0.3724(6) -0.2053(6) 1.5478(5) 0.0442(13) Uani 1 1 d . . .
H26A H -0.3633 -0.1039 1.4989 0.053 Uiso 1 1 calc R . .
P2 P 0.24603(15) 0.39712(14) 1.25603(12) 0.0379(3) Uani 1 1 d . . .
S2 S 0.47999(18) 0.49312(17) 1.19260(14) 0.0571(4) Uani 1 1 d . . .
C11 C 0.2872(10) 0.0749(7) 1.3416(7) 0.085(2) Uani 1 1 d . . .
H11A H 0.1689 0.0656 1.3062 0.127 Uiso 1 1 calc R . .
H11B H 0.3131 -0.0111 1.4180 0.127 Uiso 1 1 calc R . .
H11C H 0.3877 0.0764 1.2697 0.127 Uiso 1 1 calc R . .
C12 C 0.2748(7) 0.2202(6) 1.3893(5) 0.0477(14) Uani 1 1 d . . .
H12A H 0.3947 0.2216 1.4301 0.057 Uiso 1 1 calc R . .
C13 C 0.1161(9) 0.2373(8) 1.4997(6) 0.075(2) Uani 1 1 d . . .
H13A H -0.0004 0.2046 1.4771 0.090 Uiso 1 1 calc R . .
H13B H 0.1498 0.1741 1.5892 0.090 Uiso 1 1 calc R . .
C14 C 0.0885(8) 0.4026(8) 1.5045(6) 0.0699(18) Uani 1 1 d . . .
H14A H 0.1955 0.4299 1.5444 0.084 Uiso 1 1 calc R . .
H14B H -0.0262 0.4210 1.5613 0.084 Uiso 1 1 calc R . .
C15 C 0.0727(7) 0.4987(7) 1.3574(5) 0.0500(14) Uani 1 1 d . . .
H15A H -0.0544 0.4919 1.3296 0.060 Uiso 1 1 calc R . .
C16 C 0.1011(8) 0.6652(7) 1.3399(6) 0.0677(18) Uani 1 1 d . . .
H16A H 0.2266 0.6745 1.3638 0.102 Uiso 1 1 calc R . .
H16B H 0.0087 0.7087 1.3995 0.102 Uiso 1 1 calc R . .
H16C H 0.0862 0.7191 1.2453 0.102 Uiso 1 1 calc R . .
C31 C 0.1315(7) 0.3560(5) 1.1181(5) 0.0379(11) Uani 1 1 d . . .
C32 C -0.0501(7) 0.3130(6) 1.1352(5) 0.0503(13) Uani 1 1 d . . .
H32A H -0.1199 0.3091 1.2197 0.060 Uiso 1 1 calc R . .
C33 C -0.1301(8) 0.2757(6) 1.0306(7) 0.0601(16) Uani 1 1 d . . .
H33A H -0.2548 0.2487 1.0432 0.072 Uiso 1 1 calc R . .
C34 C -0.0285(9) 0.2778(6) 0.9073(6) 0.0589(17) Uani 1 1 d . . .
H34A H -0.0817 0.2500 0.8363 0.071 Uiso 1 1 calc R . .
C35 C 0.1508(8) 0.3206(7) 0.8898(6) 0.0595(16) Uani 1 1 d . . .
H35A H 0.2201 0.3228 0.8054 0.071 Uiso 1 1 calc R . .
C36 C 0.2327(7) 0.3608(6) 0.9926(5) 0.0477(13) Uani 1 1 d . . .
H36A H 0.3558 0.3912 0.9781 0.057 Uiso 1 1 calc R . .
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
C21 P1 C2 107.5(2) . . ?
C21 P1 C5 106.9(2) . . ?
C2 P1 C5 96.1(2) . . ?
C21 P1 S1 113.28(17) . . ?
C2 P1 S1 116.69(18) . . ?
C5 P1 S1 114.76(17) . . ?
C1 C2 C3 115.0(5) . . ?
C1 C2 P1 115.0(4) . . ?
C3 C2 P1 103.8(4) . . ?
C4 C3 C2 108.3(5) . . ?
C3 C4 C5 106.7(5) . . ?
C4 C5 C6 115.0(5) . . ?
C4 C5 P1 104.0(4) . . ?
C6 C5 P1 115.5(4) . . ?
C22 C21 C26 118.8(4) . . ?
C22 C21 P1 122.8(4) . . ?
C26 C21 P1 118.3(3) . . ?
C21 C22 C23 121.4(5) . . ?
C24 C23 C22 119.1(5) . . ?
C25 C24 C23 120.7(5) . . ?
C24 C25 C26 120.6(6) . . ?
C25 C26 C21 119.4(5) . . ?
C31 P2 C12 107.7(2) . . ?
C31 P2 C15 109.2(2) . . ?
C12 P2 C15 96.4(3) . . ?
C31 P2 S2 112.74(18) . . ?
C12 P2 S2 113.78(18) . . ?
C15 P2 S2 115.7(2) . . ?
C11 C12 C13 115.6(5) . . ?
C11 C12 P2 116.1(4) . . ?
C13 C12 P2 104.3(4) . . ?
C14 C13 C12 108.0(5) . . ?
C13 C14 C15 108.2(5) . . ?
C16 C15 C14 114.1(5) . . ?
C16 C15 P2 114.6(4) . . ?
C14 C15 P2 103.1(4) . . ?
C32 C31 C36 118.8(4) . . ?
C32 C31 P2 122.3(4) . . ?
C36 C31 P2 118.9(4) . . ?
C33 C32 C31 120.9(5) . . ?
C32 C33 C34 120.2(5) . . ?
C35 C34 C33 119.0(5) . . ?
C34 C35 C36 121.7(6) . . ?
C35 C36 C31 119.3(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 C21 1.817(5) . ?
P1 C2 1.828(5) . ?
P1 C5 1.832(5) . ?
P1 S1 1.9521(17) . ?
C1 C2 1.499(7) . ?
C2 C3 1.528(7) . ?
C3 C4 1.510(8) . ?
C4 C5 1.517(8) . ?
C5 C6 1.524(7) . ?
C21 C22 1.375(6) . ?
C21 C26 1.402(6) . ?
C22 C23 1.382(7) . ?
C23 C24 1.376(7) . ?
C24 C25 1.365(8) . ?
C25 C26 1.383(7) . ?
P2 C31 1.813(5) . ?
P2 C12 1.833(5) . ?
P2 C15 1.849(5) . ?
P2 S2 1.9532(17) . ?
C11 C12 1.506(8) . ?
C12 C13 1.537(8) . ?
C13 C14 1.508(9) . ?
C14 C15 1.534(8) . ?
C15 C16 1.516(8) . ?
C31 C32 1.381(6) . ?
C31 C36 1.390(6) . ?
C32 C33 1.375(7) . ?
C33 C34 1.376(8) . ?
C34 C35 1.365(8) . ?
C35 C36 1.379(7) . ?
