#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:18:11 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178777 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/31/4103165.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_4103165
loop_
_publ_author_name
'Jonathan J. Gammon'
'Viktoria H. Gessner'
'Greg R. Barker'
'Johan Granander'
'Adrian C. Whitwood'
'Carsten Strohmann'
'Peter O'Brien'
'Brian Kelly'
_publ_contact_author_address
;
Anorganische Chemie
Technische Universitaet Dortmund
Otto-Hahn-Strasse 6
44227 Dortmund
Germany
;
_publ_contact_author_email       carsten.strohmann@tu-dortmund.de
_publ_contact_author_fax         '0049 231 755-3807'
_publ_contact_author_name        'Carsten Strohmann'
_publ_contact_author_phone       '0049 231 755-7062'
_publ_section_title
;
 Synthesis of P-Stereogenic Compounds via Kinetic Deprotonation and
 Dynamic Thermodynamic Resolution of Phosphine Sulfides: Opposite Sense of
 Induction Using (-)-Sparteine
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13922
_journal_page_last               13927
_journal_paper_doi               10.1021/ja1060966
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H25 O P S'
_chemical_formula_weight         332.42
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2009-09-10T13:15:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5667(6)
_cell_length_b                   15.2297(14)
_cell_length_c                   18.5936(18)
_cell_measurement_temperature    173(2)
_cell_volume                     1859.5(3)
_computing_cell_refinement       'SAINTPLUS 6.02 (Bruker AXS, 1999)'
_computing_data_collection       'SMART 5.622 (Bruker AXS, 2001)'
_computing_data_reduction        'SAINTPLUS 6.02 (Bruker AXS, 1999)'
_computing_molecular_graphics    'Ortep-3 V1.073 (Farrugia, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-90 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker APEX-CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            28850
_diffrn_reflns_theta_full        27
_diffrn_reflns_theta_max         27
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.26
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_correction_T_min  0.9065
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Sadabs 2.01 (Bruker AXS, 1999)'
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         4066
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0570P)²+0.1963P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.094
_reflns_number_gt                3858
_reflns_number_total             4066
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1060966_si_001.cif
_cod_data_source_block           peter3
_cod_database_code               4103165
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
H1O H 0.039(4) 0.1913(19) 0.2470(16) 0.061(9) Uiso 1 1 d .
O1 O 0.0896(2) 0.17687(11) 0.28222(8) 0.0396(3) Uani 1 1 d .
C1 C 0.3642(3) 0.21716(13) 0.06951(10) 0.0352(4) Uani 1 1 d .
H1A H 0.5099 0.2299 0.0739 0.053 Uiso 1 1 calc R
H1B H 0.3174 0.2332 0.0212 0.053 Uiso 1 1 calc R
H1C H 0.3407 0.1544 0.0775 0.053 Uiso 1 1 calc R
C2 C 0.2707(3) 0.39706(11) 0.11533(10) 0.0345(4) Uani 1 1 d .
C3 C 0.1418(4) 0.45226(15) 0.16769(13) 0.0540(6) Uani 1 1 d .
H3A H 0.183 0.4394 0.2172 0.081 Uiso 1 1 calc R
H3B H -0.0025 0.4378 0.1614 0.081 Uiso 1 1 calc R
H3C H 0.163 0.5148 0.1577 0.081 Uiso 1 1 calc R
C4 C 0.1997(4) 0.41594(14) 0.03798(12) 0.0503(6) Uani 1 1 d .
H4A H 0.2204 0.4782 0.027 0.075 Uiso 1 1 calc R
H4B H 0.0548 0.4015 0.0334 0.075 Uiso 1 1 calc R
H4C H 0.2787 0.3801 0.0043 0.075 Uiso 1 1 calc R
C5 C 0.4963(3) 0.41898(15) 0.12418(15) 0.0552(6) Uani 1 1 d .
H5A H 0.5193 0.4807 0.1116 0.083 Uiso 1 1 calc R
H5B H 0.5772 0.3813 0.0924 0.083 Uiso 1 1 calc R
H5C H 0.5371 0.409 0.1742 0.083 Uiso 1 1 calc R
C6 C 0.3519(3) 0.26110(11) 0.22201(9) 0.0267(4) Uani 1 1 d .
H6A H 0.5007 0.2613 0.2133 0.032 Uiso 1 1 calc R
H6B H 0.3213 0.3118 0.2535 0.032 Uiso 1 1 calc R
C7 C 0.2994(3) 0.17626(12) 0.26422(9) 0.0281(4) Uani 1 1 d .
C8 C 0.4141(3) 0.17554(12) 0.33668(9) 0.0296(4) Uani 1 1 d .
C9 C 0.6145(3) 0.20347(13) 0.34300(10) 0.0366(4) Uani 1 1 d .
H9 H 0.6844 0.2247 0.3018 0.044 Uiso 1 1 calc R
C10 C 0.7142(4) 0.20066(14) 0.40901(11) 0.0464(5) Uani 1 1 d .
H10 H 0.8516 0.2196 0.4128 0.056 Uiso 1 1 calc R
C11 C 0.6125(4) 0.17023(16) 0.46909(11) 0.0512(6) Uani 1 1 d .
H11 H 0.6792 0.1689 0.5144 0.061 Uiso 1 1 calc R
C12 C 0.4155(4) 0.14204(15) 0.46320(11) 0.0493(6) Uani 1 1 d .
H12 H 0.3466 0.1207 0.5046 0.059 Uiso 1 1 calc R
C13 C 0.3147(4) 0.14417(13) 0.39743(10) 0.0379(5) Uani 1 1 d .
H13 H 0.178 0.1242 0.3941 0.046 Uiso 1 1 calc R
C14 C 0.3556(3) 0.09390(11) 0.22055(9) 0.0285(4) Uani 1 1 d .
C15 C 0.5521(3) 0.08079(12) 0.19540(10) 0.0331(4) Uani 1 1 d .
H15 H 0.6551 0.1224 0.2065 0.04 Uiso 1 1 calc R
C16 C 0.6005(4) 0.00732(14) 0.15401(11) 0.0421(5) Uani 1 1 d .
H16 H 0.7349 0 0.1361 0.051 Uiso 1 1 calc R
C17 C 0.4543(4) -0.05440(14) 0.13917(13) 0.0513(6) Uani 1 1 d .
H17 H 0.487 -0.1047 0.1113 0.062 Uiso 1 1 calc R
C18 C 0.2622(5) -0.04290(16) 0.16467(13) 0.0576(7) Uani 1 1 d .
H18 H 0.1614 -0.086 0.1548 0.069 Uiso 1 1 calc R
C19 C 0.2102(4) 0.03096(14) 0.20501(12) 0.0440(5) Uani 1 1 d .
H19 H 0.0747 0.0381 0.2219 0.053 Uiso 1 1 calc R
P P 0.22502(6) 0.27990(3) 0.13558(2) 0.02435(11) Uani 1 1 d .
S S -0.06672(7) 0.24813(4) 0.13480(3) 0.04220(14) Uani 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 0 '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'
O O 0.0106 0.006 '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
C5 C2 C4 110.7(2)
C5 C2 C3 110.21(19)
C4 C2 C3 108.82(18)
C5 C2 P 110.27(14)
C4 C2 P 108.77(13)
C3 C2 P 108.02(15)
C7 C6 P 118.22(12)
O1 C7 C14 111.26(15)
O1 C7 C8 105.55(14)
C14 C7 C8 109.75(14)
O1 C7 C6 109.27(15)
C14 C7 C6 111.03(13)
C8 C7 C6 109.83(14)
C9 C8 C13 118.82(17)
C9 C8 C7 122.29(16)
C13 C8 C7 118.88(17)
C8 C9 C10 120.7(2)
C11 C10 C9 119.7(2)
C12 C11 C10 119.9(2)
C11 C12 C13 120.9(2)
C8 C13 C12 119.9(2)
C19 C14 C15 118.15(18)
C19 C14 C7 120.65(17)
C15 C14 C7 121.20(16)
C14 C15 C16 120.90(19)
C17 C16 C15 120.1(2)
C18 C17 C16 119.4(2)
C17 C18 C19 121.3(2)
C14 C19 C18 120.2(2)
C1 P C6 106.50(9)
C1 P C2 106.88(10)
C6 P C2 104.81(8)
C1 P S 110.87(7)
C6 P S 114.14(6)
C2 P S 113.09(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.418(2)
C1 P 1.8046(18)
C2 C5 1.528(3)
C2 C4 1.539(3)
C2 C3 1.540(3)
C2 P 1.8481(18)
C6 C7 1.551(2)
C6 P 1.8329(17)
C7 C14 1.539(3)
C7 C8 1.543(2)
C8 C9 1.388(3)
C8 C13 1.389(3)
C9 C10 1.392(3)
C10 C11 1.382(3)
C11 C12 1.367(4)
C12 C13 1.391(3)
C14 C19 1.383(3)
C14 C15 1.387(3)
C15 C16 1.395(3)
C16 C17 1.371(3)
C17 C18 1.359(4)
C18 C19 1.394(3)
P S 1.9760(6)
