#------------------------------------------------------------------------------
#$Date: 2015-10-09 10:55:22 +0300 (Fri, 09 Oct 2015) $
#$Revision: 161211 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/63/7036350.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_7036350
loop_
_publ_author_name
'Chang, Ting-Wei'
'Ho, Pei-Yun'
'Mao, Kuo-Chung'
'Hong, Fung-E'
_publ_section_title
;
 Developing five-membered heterocycle substituted phosphinous acids as
 ligands for palladium-catalyzed Suzuki-Miyaura and Catellani reactions.
;
_journal_issue                   39
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              17129
_journal_page_last               17142
_journal_paper_doi               10.1039/c5dt02611c
_journal_volume                  44
_journal_year                    2015
_chemical_formula_sum            'C12 H15 O P S'
_chemical_formula_weight         238.27
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_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_method           SHELXL-97
_audit_update_record
;
2015-05-22 deposited with the CCDC.
2015-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2832(2)
_cell_length_b                   11.2563(2)
_cell_length_c                   11.6948(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1222.04(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.946
_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  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16313
_diffrn_reflns_theta_full        29.24
_diffrn_reflns_theta_max         29.24
_diffrn_reflns_theta_min         2.84
_exptl_absorpt_coefficient_mu    0.367
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.46(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         3046
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.131
_refine_ls_shift/su_mean         0.018
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0471P)²+0.5218P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0881
_reflns_number_gt                2910
_reflns_number_total             3046
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5dt02611c2.cif
_cod_data_source_block           hong276m
_cod_depositor_comments
'Adding full bibliography for 7036349--7036358.cif.'
_cod_database_code               7036350
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
P P 0.23586(5) 0.10792(4) 0.09430(4) 0.02449(12) Uani 1 1 d .
H13A H 0.1980 0.0852 0.0192 0.029 Uiso 1 1 calc R
S S 0.38640(5) 0.33337(5) 0.17830(4) 0.02961(12) Uani 1 1 d .
C8 C 0.25480(19) 0.26627(16) 0.09334(15) 0.0236(3) Uani 1 1 d .
C6 C 0.22366(19) 0.46700(17) 0.05058(15) 0.0236(4) Uani 1 1 d .
C7 C 0.1768(2) 0.34677(17) 0.03061(16) 0.0253(4) Uani 1 1 d .
H7A H 0.1024 0.3262 -0.0189 0.030 Uiso 1 1 calc R
C9 C 0.0998(2) 0.06739(17) 0.19885(17) 0.0271(4) Uani 1 1 d .
C3 C 0.3479(2) 0.68336(18) 0.10977(19) 0.0332(4) Uani 1 1 d .
H3A H 0.3883 0.7565 0.1284 0.040 Uiso 1 1 calc R
C2 C 0.4001(2) 0.58192(19) 0.16087(18) 0.0321(4) Uani 1 1 d .
H2A H 0.4743 0.5853 0.2142 0.039 Uiso 1 1 calc R
O O 0.37555(16) 0.04566(14) 0.10827(14) 0.0382(4) Uani 1 1 d .
C5 C 0.1725(2) 0.57294(17) 0.00039(16) 0.0272(4) Uani 1 1 d .
H5A H 0.0973 0.5710 -0.0522 0.033 Uiso 1 1 calc R
C4 C 0.2350(2) 0.67858(18) 0.03021(18) 0.0323(4) Uani 1 1 d .
H4A H 0.2019 0.7486 -0.0029 0.039 Uiso 1 1 calc R
C11 C -0.0384(2) 0.13557(18) 0.1762(2) 0.0329(4) Uani 1 1 d .
H11A H -0.1094 0.1139 0.2321 0.049 Uiso 1 1 calc R
H11B H -0.0733 0.1167 0.1011 0.049 Uiso 1 1 calc R
H11C H -0.0197 0.2193 0.1811 0.049 Uiso 1 1 calc R
C1 C 0.3373(2) 0.47312(18) 0.12965(16) 0.0252(4) Uani 1 1 d .
C10 C 0.1570(3) 0.0963(3) 0.3179(2) 0.0584(8) Uani 1 1 d .
H10A H 0.0861 0.0752 0.3741 0.088 Uiso 1 1 calc R
H10B H 0.1770 0.1798 0.3230 0.088 Uiso 1 1 calc R
H10C H 0.2438 0.0522 0.3316 0.088 Uiso 1 1 calc R
C12 C 0.0691(3) -0.0651(2) 0.1831(3) 0.0666(10) Uani 1 1 d .
H12A H -0.0023 -0.0900 0.2375 0.100 Uiso 1 1 calc R
H12B H 0.1562 -0.1094 0.1951 0.100 Uiso 1 1 calc R
H12C H 0.0343 -0.0790 0.1070 0.100 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'
O O 0.0106 0.0060 '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
O P C8 112.65(9)
O P C9 114.54(9)
C8 P C9 108.81(9)
O P H13A 106.8
C8 P H13A 106.8
C9 P H13A 106.8
C1 S C8 91.24(9)
C7 C8 S 112.82(14)
C7 C8 P 127.48(15)
S C8 P 119.70(11)
C1 C6 C5 119.04(17)
C1 C6 C7 112.32(17)
C5 C6 C7 128.64(17)
C8 C7 C6 111.96(17)
C8 C7 H7A 124.0
C6 C7 H7A 124.0
C10 C9 C11 110.20(19)
C10 C9 C12 112.5(2)
C11 C9 C12 108.37(19)
C10 C9 P 108.58(15)
C11 C9 P 110.07(14)
C12 C9 P 107.06(15)
C2 C3 C4 121.28(19)
C2 C3 H3A 119.4
C4 C3 H3A 119.4
C3 C2 C1 117.65(18)
C3 C2 H2A 121.2
C1 C2 H2A 121.2
C4 C5 C6 119.03(18)
C4 C5 H5A 120.5
C6 C5 H5A 120.5
C5 C4 C3 121.29(19)
C5 C4 H4A 119.4
C3 C4 H4A 119.4
C9 C11 H11A 109.5
C9 C11 H11B 109.5
H11A C11 H11B 109.5
C9 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C6 C1 C2 121.71(18)
C6 C1 S 111.66(14)
C2 C1 S 126.63(15)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C9 C12 H12A 109.5
C9 C12 H12B 109.5
H12A C12 H12B 109.5
C9 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P O 1.4830(15)
P C8 1.7911(19)
P C9 1.8164(19)
P H13A 0.9800
S C1 1.734(2)
S C8 1.7465(18)
C8 C7 1.373(3)
C6 C1 1.404(3)
C6 C5 1.412(3)
C6 C7 1.441(3)
C7 H7A 0.9300
C9 C10 1.525(3)
C9 C11 1.518(3)
C9 C12 1.529(3)
C3 C2 1.377(3)
C3 C4 1.403(3)
C3 H3A 0.9300
C2 C1 1.405(3)
C2 H2A 0.9300
C5 C4 1.368(3)
C5 H5A 0.9300
C4 H4A 0.9300
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
