#------------------------------------------------------------------------------
#$Date: 2018-01-06 04:17:32 +0200 (Sat, 06 Jan 2018) $
#$Revision: 204849 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/30/4033038.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_4033038
loop_
_publ_author_name
'Liu, Li-Juan'
'Wang, Wei-Min'
'Yao, Lan'
'Meng, Fan-Jie'
'Sun, Yong-Ming'
'Xu, Hao'
'Xu, Zhong-Yuan'
'Li, Qiang'
'Zhao, Chang-Qiu'
'Han, Li-Biao'
_publ_section_title
;
 Reinvestigation of the Substitutions Reaction of Stereogenic Phosphoryl
 Compounds: Stereochemistry, Mechanism, and Applications.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11990
_journal_page_last               12002
_journal_paper_doi               10.1021/acs.joc.7b01326
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration s
_chemical_formula_sum            'C23 H31 N0 O2 P'
_chemical_formula_weight         370.45
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7278(6)
_cell_length_b                   17.5633(19)
_cell_length_c                   21.791(2)
_cell_measurement_reflns_used    1055
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.246
_cell_measurement_theta_min      2.979
_cell_volume                     2192.2(4)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.1094
_diffrn_reflns_av_sigmaI/netI    0.1475
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11172
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.9931
_exptl_absorpt_correction_T_min  0.9467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.669
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.669
_refine_ls_R_factor_all          0.1436
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1079P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1655
_reflns_number_gt                1722
_reflns_number_total             3844
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b01326_si_002.cif
_cod_data_source_block           100602a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4033038--4033039.cif.
;
_cod_original_sg_symbol_H-M      'P2(1)2(1)2(1) '
_cod_database_code               4033038
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
P1 P 0.5101(2) 0.88212(6) 0.03209(5) 0.0517(3) Uani 1 1 d .
O1 O 0.5819(5) 0.96954(14) 0.02642(14) 0.0538(8) Uani 1 1 d .
O2 O 0.2609(5) 0.86655(15) 0.01950(15) 0.0598(9) Uani 1 1 d .
C1 C 0.2426(13) 1.1072(3) -0.0743(2) 0.0877(18) Uani 1 1 d .
H1 H 0.0853 1.0870 -0.0675 0.105 Uiso 1 1 calc R
C2 C 0.4183(10) 1.0466(3) -0.0547(2) 0.0730(17) Uani 1 1 d .
H2A H 0.3907 1.0007 -0.0783 0.088 Uiso 1 1 calc R
H2B H 0.5745 1.0644 -0.0641 0.088 Uiso 1 1 calc R
C3 C 0.4058(9) 1.0276(2) 0.0120(2) 0.0556(13) Uani 1 1 d .
H3 H 0.2504 1.0073 0.0213 0.067 Uiso 1 1 calc R
C4 C 0.4509(9) 1.0976(2) 0.0523(2) 0.0568(14) Uani 1 1 d .
H4 H 0.6029 1.1182 0.0401 0.068 Uiso 1 1 calc R
C5 C 0.2673(11) 1.1570(3) 0.0346(3) 0.0838(17) Uani 1 1 d .
H5A H 0.1134 1.1374 0.0443 0.101 Uiso 1 1 calc R
H5B H 0.2918 1.2027 0.0587 0.101 Uiso 1 1 calc R
C6 C 0.2758(13) 1.1771(3) -0.0322(3) 0.0920(19) Uani 1 1 d .
H6A H 0.4252 1.2006 -0.0412 0.110 Uiso 1 1 calc R
H6B H 0.1546 1.2141 -0.0410 0.110 Uiso 1 1 calc R
C7 C 0.2651(18) 1.1275(4) -0.1411(3) 0.141(3) Uani 1 1 d .
H7A H 0.4122 1.1523 -0.1479 0.212 Uiso 1 1 calc R
H7B H 0.1404 1.1611 -0.1525 0.212 Uiso 1 1 calc R
H7C H 0.2571 1.0820 -0.1654 0.212 Uiso 1 1 calc R
C8 C 0.4665(12) 1.0799(3) 0.1213(2) 0.0775(16) Uani 1 1 d .
H8 H 0.5899 1.0418 0.1264 0.093 Uiso 1 1 calc R
C9 C 0.5430(15) 1.1508(3) 0.1573(2) 0.120(3) Uani 1 1 d .
H9A H 0.4128 1.1847 0.1617 0.180 Uiso 1 1 calc R
H9B H 0.6663 1.1761 0.1355 0.180 Uiso 1 1 calc R
H9C H 0.5979 1.1358 0.1971 0.180 Uiso 1 1 calc R
C10 C 0.2474(16) 1.0463(4) 0.1478(3) 0.133(3) Uani 1 1 d .
H10A H 0.2657 1.0400 0.1913 0.199 Uiso 1 1 calc R
H10B H 0.2183 0.9976 0.1293 0.199 Uiso 1 1 calc R
H10C H 0.1183 1.0797 0.1398 0.199 Uiso 1 1 calc R
C11 C 0.5917(9) 0.8564(2) 0.1089(2) 0.0526(13) Uani 1 1 d .
C12 C 0.7992(10) 0.8805(3) 0.1354(3) 0.0763(15) Uani 1 1 d .
H12 H 0.9034 0.9097 0.1126 0.092 Uiso 1 1 calc R
C13 C 0.8522(12) 0.8617(4) 0.1950(3) 0.0912(19) Uani 1 1 d .
H13 H 0.9907 0.8787 0.2126 0.109 Uiso 1 1 calc R
C14 C 0.7011(14) 0.8179(4) 0.2286(3) 0.097(2) Uani 1 1 d .
H14 H 0.7367 0.8054 0.2690 0.116 Uiso 1 1 calc R
C15 C 0.4973(15) 0.7924(3) 0.2026(3) 0.0944(18) Uani 1 1 d .
H15 H 0.3963 0.7617 0.2251 0.113 Uiso 1 1 calc R
C16 C 0.4425(10) 0.8121(3) 0.1434(2) 0.0734(17) Uani 1 1 d .
H16 H 0.3029 0.7953 0.1263 0.088 Uiso 1 1 calc R
C17 C 0.7100(9) 0.8351(2) -0.0192(2) 0.0597(13) Uani 1 1 d .
H17A H 0.8685 0.8432 -0.0049 0.072 Uiso 1 1 calc R
H17B H 0.6797 0.7808 -0.0186 0.072 Uiso 1 1 calc R
C18 C 0.6881(9) 0.8640(3) -0.0837(2) 0.0559(13) Uani 1 1 d .
C19 C 0.8537(10) 0.9113(3) -0.1088(3) 0.0754(16) Uani 1 1 d .
H19 H 0.9852 0.9238 -0.0858 0.090 Uiso 1 1 calc R
C20 C 0.8295(13) 0.9408(4) -0.1671(3) 0.101(2) Uani 1 1 d .
H20 H 0.9433 0.9730 -0.1831 0.121 Uiso 1 1 calc R
C21 C 0.6371(15) 0.9225(4) -0.2014(3) 0.105(2) Uani 1 1 d .
H21 H 0.6183 0.9432 -0.2403 0.126 Uiso 1 1 calc R
C22 C 0.4727(13) 0.8737(4) -0.1785(3) 0.0901(18) Uani 1 1 d .
H22 H 0.3441 0.8606 -0.2023 0.108 Uiso 1 1 calc R
C23 C 0.4962(11) 0.8441(3) -0.1204(2) 0.0721(14) Uani 1 1 d .
H23 H 0.3842 0.8106 -0.1053 0.087 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'
N N 0.0061 0.0033 '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
O2 P1 O1 114.37(17)
O2 P1 C11 112.2(2)
O1 P1 C11 104.29(19)
O2 P1 C17 114.5(2)
O1 P1 C17 103.27(19)
C11 P1 C17 107.3(2)
C3 O1 P1 120.5(3)
C7 C1 C2 112.3(6)
C7 C1 C6 112.1(5)
C2 C1 C6 107.9(4)
C3 C2 C1 113.4(5)
O1 C3 C2 109.3(4)
O1 C3 C4 108.5(4)
C2 C3 C4 111.8(4)
C5 C4 C3 106.6(4)
C5 C4 C8 115.2(4)
C3 C4 C8 114.1(4)
C6 C5 C4 112.6(5)
C5 C6 C1 112.7(4)
C10 C8 C9 111.2(5)
C10 C8 C4 114.0(5)
C9 C8 C4 110.6(4)
C12 C11 C16 118.5(5)
C12 C11 P1 122.3(4)
C16 C11 P1 119.2(4)
C13 C12 C11 120.6(5)
C12 C13 C14 120.0(6)
C13 C14 C15 120.0(6)
C16 C15 C14 120.0(6)
C15 C16 C11 120.9(6)
C18 C17 P1 111.9(3)
C19 C18 C23 117.7(5)
C19 C18 C17 121.3(5)
C23 C18 C17 121.0(5)
C20 C19 C18 121.6(6)
C19 C20 C21 119.7(7)
C20 C21 C22 120.1(7)
C23 C22 C21 120.4(6)
C22 C23 C18 120.4(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O2 1.479(3)
P1 O1 1.594(3)
P1 C11 1.796(5)
P1 C17 1.800(5)
O1 C3 1.469(5)
C1 C7 1.503(8)
C1 C2 1.526(7)
C1 C6 1.544(7)
C2 C3 1.492(6)
C3 C4 1.533(6)
C4 C5 1.531(6)
C4 C8 1.537(6)
C5 C6 1.497(7)
C8 C10 1.502(9)
C8 C9 1.535(7)
C11 C12 1.387(6)
C11 C16 1.379(6)
C12 C13 1.375(7)
C13 C14 1.370(8)
C14 C15 1.373(9)
C15 C16 1.372(7)
C17 C18 1.500(6)
C18 C19 1.375(6)
C18 C23 1.403(7)
C19 C20 1.380(7)
C20 C21 1.370(9)
C21 C22 1.368(8)
C22 C23 1.376(7)
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
O2 P1 O1 C3 2.1(4)
C11 P1 O1 C3 -120.8(3)
C17 P1 O1 C3 127.1(3)
C7 C1 C2 C3 177.8(5)
C6 C1 C2 C3 53.7(7)
P1 O1 C3 C2 -99.6(4)
P1 O1 C3 C4 138.3(3)
C1 C2 C3 O1 -179.5(4)
C1 C2 C3 C4 -59.3(6)
O1 C3 C4 C5 178.7(4)
C2 C3 C4 C5 58.0(5)
O1 C3 C4 C8 -53.1(6)
C2 C3 C4 C8 -173.7(5)
C3 C4 C5 C6 -57.8(6)
C8 C4 C5 C6 174.6(5)
C4 C5 C6 C1 57.7(7)
C7 C1 C6 C5 -176.8(6)
C2 C1 C6 C5 -52.6(7)
C5 C4 C8 C10 62.5(6)
C3 C4 C8 C10 -61.2(6)
C5 C4 C8 C9 -63.6(7)
C3 C4 C8 C9 172.7(5)
O2 P1 C11 C12 -165.8(4)
O1 P1 C11 C12 -41.4(4)
C17 P1 C11 C12 67.7(4)
O2 P1 C11 C16 13.4(4)
O1 P1 C11 C16 137.7(4)
C17 P1 C11 C16 -113.1(4)
C16 C11 C12 C13 -1.2(8)
P1 C11 C12 C13 177.9(4)
C11 C12 C13 C14 1.0(9)
C12 C13 C14 C15 0.3(10)
C13 C14 C15 C16 -1.3(10)
C14 C15 C16 C11 1.0(9)
C12 C11 C16 C15 0.2(7)
P1 C11 C16 C15 -179.0(4)
O2 P1 C17 C18 65.8(4)
O1 P1 C17 C18 -59.2(4)
C11 P1 C17 C18 -169.0(3)
P1 C17 C18 C19 105.7(5)
P1 C17 C18 C23 -73.7(5)
C23 C18 C19 C20 2.3(7)
C17 C18 C19 C20 -177.1(5)
C18 C19 C20 C21 -0.4(9)
C19 C20 C21 C22 -1.6(10)
C20 C21 C22 C23 1.5(10)
C21 C22 C23 C18 0.6(8)
C19 C18 C23 C22 -2.4(7)
C17 C18 C23 C22 177.0(4)
