#------------------------------------------------------------------------------
#$Date: 2020-07-14 02:17:28 +0300 (Tue, 14 Jul 2020) $
#$Revision: 254251 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/85/4038576.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_4038576
loop_
_publ_author_name
'Kuwabara, Kazuma'
'Maekawa, Yuuki'
'Minoura, Mao'
'Maruyama, Toshifumi'
'Murai, Toshiaki'
_publ_section_title
;
 Chemo- and Stereoselective Alcoholysis of Binaphthyl Phosphonothioates:
 Straightforward Access to both Stereoisomers of Biologically Relevant
 P-Stereogenic Phosphonothioates.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00687
_journal_year                    2020
_chemical_formula_sum            'C14 H25 O7 P S'
_chemical_formula_weight         368.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'SHELXT-2014 (Sheldrick 2014)'
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9034(17)
_cell_length_b                   11.952(2)
_cell_length_c                   16.993(3)
_cell_measurement_reflns_used    178
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      10.11
_cell_measurement_theta_min      2.22
_cell_volume                     1808.3(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker APEX3'
_computing_publication_material  'Bruker APEX3'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Dectris PILATUS-CdTe'
_diffrn_measurement_method       'Phi scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.4118
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            41908
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        14.305
_diffrn_reflns_theta_max         15.505
_diffrn_reflns_theta_min         1.207
_diffrn_source                   'BL02B1 SPring-8'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.744
_exptl_absorpt_correction_T_min  0.464
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.010
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1762 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_coef       0.077(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         4143
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0247
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0376P)²+0.4268P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0659
_refine_ls_wR_factor_ref         0.0660
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4117
_reflns_number_total             4143
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00687_si_002.cif
_cod_data_source_block           191201_06_TM01_0m_a
_cod_database_code               4038576
_shelx_shelxl_version_number     2014/7
_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   0.999
_shelx_estimated_absorpt_t_max   0.999
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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
P1 P -0.00165(5) 0.55813(4) 0.60236(2) 0.01874(11) Uani 1 1 d . . . . .
S1 S -0.05764(6) 0.57021(5) 0.49322(3) 0.03163(13) Uani 1 1 d . . . . .
O1 O -0.09530(15) 0.63277(11) 0.66148(8) 0.0245(3) Uani 1 1 d . . . . .
O2 O 0.16480(13) 0.59959(10) 0.62124(7) 0.0183(2) Uani 1 1 d . . . . .
C1 C -0.0255(2) 0.42356(14) 0.64647(10) 0.0226(3) Uani 1 1 d . . . . .
H1A H 0.0260 0.4219 0.6974 0.034 Uiso 1 1 calc R U . . .
H1B H 0.0172 0.3661 0.6119 0.034 Uiso 1 1 calc R U . . .
H1C H -0.1328 0.4089 0.6542 0.034 Uiso 1 1 calc R U . . .
C2 C -0.1060(3) 0.75105(17) 0.64777(15) 0.0384(5) Uani 1 1 d . . . . .
H2A H -0.0049 0.7829 0.6434 0.058 Uiso 1 1 calc R U . . .
H2B H -0.1590 0.7865 0.6917 0.058 Uiso 1 1 calc R U . . .
H2C H -0.1614 0.7646 0.5988 0.058 Uiso 1 1 calc R U . . .
C3 C 0.28528(18) 0.59678(13) 0.56448(10) 0.0182(3) Uani 1 1 d . . . . .
H3A H 0.3447 0.6666 0.5679 0.022 Uiso 1 1 calc R U . . .
H3B H 0.2434 0.5911 0.5107 0.022 Uiso 1 1 calc R U . . .
C4 C 0.38476(18) 0.49763(12) 0.58092(9) 0.0154(3) Uani 1 1 d . . . . .
H4A H 0.4183 0.4998 0.6371 0.018 Uiso 1 1 calc R U . . .
O3 O 0.29530(13) 0.39996(9) 0.56816(7) 0.0162(2) Uani 1 1 d . . . . .
C5 C 0.36191(18) 0.30303(13) 0.59853(9) 0.0164(3) Uani 1 1 d . . . . .
H5A H 0.3092 0.2356 0.5772 0.020 Uiso 1 1 calc R U . . .
C6 C 0.53124(18) 0.29359(12) 0.58195(9) 0.0159(3) Uani 1 1 d . . . . .
H6A H 0.5568 0.2155 0.5656 0.019 Uiso 1 1 calc R U . . .
C7 C 0.58764(18) 0.37614(13) 0.52100(9) 0.0163(3) Uani 1 1 d . . . . .
H7A H 0.6999 0.3792 0.5215 0.020 Uiso 1 1 calc R U . . .
C8 C 0.52142(19) 0.49494(13) 0.52744(10) 0.0179(3) Uani 1 1 d . . . . .
H8A H 0.5994 0.5487 0.5465 0.022 Uiso 1 1 calc R U . . .
O4 O 0.35218(13) 0.30324(10) 0.68212(7) 0.0190(2) Uani 1 1 d . . . . .
C9 C 0.4975(2) 0.28098(13) 0.71405(9) 0.0178(3) Uani 1 1 d . . . . .
O5 O 0.60027(13) 0.31877(10) 0.65547(7) 0.0187(2) Uani 1 1 d . . . . .
C10 C 0.5211(2) 0.34947(16) 0.78732(11) 0.0285(4) Uani 1 1 d . . . . .
H10A H 0.5084 0.4290 0.7749 0.043 Uiso 1 1 calc R U . . .
H10B H 0.6228 0.3367 0.8075 0.043 Uiso 1 1 calc R U . . .
H10C H 0.4475 0.3274 0.8273 0.043 Uiso 1 1 calc R U . . .
C11 C 0.5147(2) 0.15638(14) 0.72884(10) 0.0224(3) Uani 1 1 d . . . . .
H11A H 0.4363 0.1313 0.7652 0.034 Uiso 1 1 calc R U . . .
H11B H 0.6136 0.1416 0.7519 0.034 Uiso 1 1 calc R U . . .
H11C H 0.5053 0.1158 0.6790 0.034 Uiso 1 1 calc R U . . .
O6 O 0.53516(14) 0.33635(9) 0.44704(7) 0.0192(3) Uani 1 1 d . . . . .
C12 C 0.51127(18) 0.43102(13) 0.39724(9) 0.0189(3) Uani 1 1 d . . . . .
O7 O 0.47755(17) 0.52170(11) 0.44912(7) 0.0272(3) Uani 1 1 d . . . . .
C13 C 0.3757(2) 0.40741(19) 0.34695(13) 0.0342(5) Uani 1 1 d . . . . .
H13A H 0.2899 0.3892 0.3808 0.051 Uiso 1 1 calc R U . . .
H13B H 0.3969 0.3440 0.3121 0.051 Uiso 1 1 calc R U . . .
H13C H 0.3519 0.4736 0.3153 0.051 Uiso 1 1 calc R U . . .
C14 C 0.65126(19) 0.45760(15) 0.35077(10) 0.0204(3) Uani 1 1 d . . . . .
H14A H 0.6341 0.5247 0.3188 0.031 Uiso 1 1 calc R U . . .
H14B H 0.6756 0.3944 0.3163 0.031 Uiso 1 1 calc R U . . .
H14C H 0.7350 0.4709 0.3870 0.031 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 -0.0001 0.0005 '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 0.0017 0.0018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.0346 0.0307 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.0441 0.0406 '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
O1 P1 O2 100.77(7) . . ?
O1 P1 C1 100.29(8) . . ?
O2 P1 C1 107.79(8) . . ?
O1 P1 S1 115.66(6) . . ?
O2 P1 S1 114.26(5) . . ?
C1 P1 S1 116.15(6) . . ?
C2 O1 P1 119.17(13) . . ?
C3 O2 P1 123.30(10) . . ?
P1 C1 H1A 109.5 . . ?
P1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
P1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 H2A 109.5 . . ?
O1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
O1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O2 C3 C4 109.37(13) . . ?
O2 C3 H3A 109.8 . . ?
C4 C3 H3A 109.8 . . ?
O2 C3 H3B 109.8 . . ?
C4 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
O3 C4 C3 106.66(13) . . ?
O3 C4 C8 109.78(12) . . ?
C3 C4 C8 112.14(13) . . ?
O3 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C8 C4 H4A 109.4 . . ?
C5 O3 C4 112.56(12) . . ?
O3 C5 O4 109.92(13) . . ?
O3 C5 C6 114.11(13) . . ?
O4 C5 C6 104.04(12) . . ?
O3 C5 H5A 109.5 . . ?
O4 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
O5 C6 C7 108.59(13) . . ?
O5 C6 C5 104.28(12) . . ?
C7 C6 C5 113.71(13) . . ?
O5 C6 H6A 110.0 . . ?
C7 C6 H6A 110.0 . . ?
C5 C6 H6A 110.0 . . ?
O6 C7 C6 106.09(12) . . ?
O6 C7 C8 104.19(12) . . ?
C6 C7 C8 115.10(13) . . ?
O6 C7 H7A 110.4 . . ?
C6 C7 H7A 110.4 . . ?
C8 C7 H7A 110.4 . . ?
O7 C8 C4 109.56(14) . . ?
O7 C8 C7 104.21(12) . . ?
C4 C8 C7 111.62(12) . . ?
O7 C8 H8A 110.4 . . ?
C4 C8 H8A 110.4 . . ?
C7 C8 H8A 110.4 . . ?
C5 O4 C9 108.89(12) . . ?
O5 C9 O4 104.90(12) . . ?
O5 C9 C10 108.42(14) . . ?
O4 C9 C10 109.85(15) . . ?
O5 C9 C11 111.21(14) . . ?
O4 C9 C11 109.69(13) . . ?
C10 C9 C11 112.49(14) . . ?
C6 O5 C9 105.59(12) . . ?
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 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 . . ?
C7 O6 C12 107.90(12) . . ?
O6 C12 O7 105.45(12) . . ?
O6 C12 C13 107.88(14) . . ?
O7 C12 C13 108.90(15) . . ?
O6 C12 C14 110.71(13) . . ?
O7 C12 C14 109.68(13) . . ?
C13 C12 C14 113.86(14) . . ?
C8 O7 C12 110.42(12) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
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 O1 1.5813(13) . ?
P1 O2 1.5952(13) . ?
P1 C1 1.7870(17) . ?
P1 S1 1.9260(7) . ?
O1 C2 1.436(2) . ?
O2 C3 1.4430(19) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.506(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O3 1.4297(18) . ?
C4 C8 1.519(2) . ?
C4 H4A 1.0000 . ?
O3 C5 1.4001(18) . ?
C5 O4 1.4232(19) . ?
C5 C6 1.538(2) . ?
C5 H5A 1.0000 . ?
C6 O5 1.4246(19) . ?
C6 C7 1.516(2) . ?
C6 H6A 1.0000 . ?
C7 O6 1.4226(19) . ?
C7 C8 1.541(2) . ?
C7 H7A 1.0000 . ?
C8 O7 1.423(2) . ?
C8 H8A 1.0000 . ?
O4 C9 1.428(2) . ?
C9 O5 1.425(2) . ?
C9 C10 1.505(2) . ?
C9 C11 1.518(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
O6 C12 1.4289(18) . ?
C12 O7 1.429(2) . ?
C12 C13 1.506(2) . ?
C12 C14 1.509(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
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
O2 P1 O1 C2 69.34(17) . . . . ?
C1 P1 O1 C2 179.87(16) . . . . ?
S1 P1 O1 C2 -54.39(17) . . . . ?
O1 P1 O2 C3 -152.33(12) . . . . ?
C1 P1 O2 C3 103.07(13) . . . . ?
S1 P1 O2 C3 -27.64(13) . . . . ?
P1 O2 C3 C4 -101.50(14) . . . . ?
O2 C3 C4 O3 64.51(16) . . . . ?
O2 C3 C4 C8 -175.29(13) . . . . ?
C3 C4 O3 C5 -166.12(13) . . . . ?
C8 C4 O3 C5 72.17(16) . . . . ?
C4 O3 C5 O4 73.29(16) . . . . ?
C4 O3 C5 C6 -43.12(17) . . . . ?
O3 C5 C6 O5 105.10(14) . . . . ?
O4 C5 C6 O5 -14.67(15) . . . . ?
O3 C5 C6 C7 -13.01(18) . . . . ?
O4 C5 C6 C7 -132.79(13) . . . . ?
O5 C6 C7 O6 170.71(12) . . . . ?
C5 C6 C7 O6 -73.69(16) . . . . ?
O5 C6 C7 C8 -74.65(17) . . . . ?
C5 C6 C7 C8 40.95(19) . . . . ?
O3 C4 C8 O7 75.33(15) . . . . ?
C3 C4 C8 O7 -43.04(18) . . . . ?
O3 C4 C8 C7 -39.57(18) . . . . ?
C3 C4 C8 C7 -157.94(13) . . . . ?
O6 C7 C8 O7 -16.49(16) . . . . ?
C6 C7 C8 O7 -132.23(14) . . . . ?
O6 C7 C8 C4 101.66(15) . . . . ?
C6 C7 C8 C4 -14.1(2) . . . . ?
O3 C5 O4 C9 -129.66(13) . . . . ?
C6 C5 O4 C9 -7.08(16) . . . . ?
C5 O4 C9 O5 26.42(15) . . . . ?
C5 O4 C9 C10 142.76(13) . . . . ?
C5 O4 C9 C11 -93.11(15) . . . . ?
C7 C6 O5 C9 152.56(13) . . . . ?
C5 C6 O5 C9 30.99(15) . . . . ?
O4 C9 O5 C6 -35.92(15) . . . . ?
C10 C9 O5 C6 -153.23(14) . . . . ?
C11 C9 O5 C6 82.59(16) . . . . ?
C6 C7 O6 C12 149.21(13) . . . . ?
C8 C7 O6 C12 27.32(15) . . . . ?
C7 O6 C12 O7 -27.78(16) . . . . ?
C7 O6 C12 C13 -144.03(15) . . . . ?
C7 O6 C12 C14 90.77(15) . . . . ?
C4 C8 O7 C12 -119.63(14) . . . . ?
C7 C8 O7 C12 -0.08(17) . . . . ?
O6 C12 O7 C8 16.64(18) . . . . ?
C13 C12 O7 C8 132.20(15) . . . . ?
C14 C12 O7 C8 -102.60(15) . . . . ?
