#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:00:49 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180327 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/41/7154152.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_7154152
loop_
_publ_author_name
'Sun, Yong-Ming'
'Xin, Nana'
'Xu, Zhong-Yuan'
'Liu, Li-Juan'
'Meng, Fan-Jie'
'Zhang, He'
'Fu, Bao-Ci'
'Liang, Qiu-Ju'
'Zheng, Hong-Xing'
'Sun, Li-Jun'
'Zhao, Chang-Qiu'
'Han, Li-Biao'
_publ_section_title
;
 Addition of optically pure H-phosphinate to ketones: selectivity,
 stereochemistry and mechanism.
;
_journal_issue                   46
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9457
_journal_paper_doi               10.1039/c4ob01574f
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C25 H30 N0 O4 P'
_chemical_formula_weight         425.46
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 92.5340(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.436(13)
_cell_length_b                   5.7781(7)
_cell_length_c                   15.9687(16)
_cell_measurement_temperature    298(2)
_cell_volume                     1146.3(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.1238
_diffrn_reflns_av_sigmaI/netI    0.1382
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5868
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.97
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.9825
_exptl_absorpt_correction_T_min  0.9392
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             454
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.033
_refine_diff_density_min         -0.990
_refine_diff_density_rms         0.187
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         3683
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.1811
_refine_ls_R_factor_gt           0.1367
_refine_ls_shift/su_max          0.100
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3229
_refine_ls_wR_factor_ref         0.3557
_reflns_number_gt                2107
_reflns_number_total             3683
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob01574f2.cif
_cod_data_source_block           121201b
_cod_depositor_comments
'Adding full bibliography for 7154151--7154157.cif.'
_cod_database_code               7154152
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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 0.18598(18) 0.1980(4) 0.79796(15) 0.0442(7) Uani 1 1 d .
O3 O 0.0644(5) 0.5741(12) 0.7778(4) 0.0499(17) Uani 1 1 d U
H3 H 0.0016 0.6157 0.7710 0.075 Uiso 1 1 calc R
O2 O 0.1944(6) -0.0499(11) 0.7747(4) 0.0565(18) Uani 1 1 d U
O4 O 0.2866(5) 0.3465(12) 0.7806(4) 0.0479(17) Uani 1 1 d U
C11 C 0.1653(6) 0.2246(17) 0.9068(5) 0.040(2) Uani 1 1 d .
C12 C 0.1142(7) 0.0493(19) 0.9482(6) 0.047(2) Uani 1 1 d .
H12 H 0.0926 -0.0822 0.9183 0.057 Uiso 1 1 calc R
C19 C 0.1006(9) 0.3678(17) 0.6487(6) 0.053(3) Uani 1 1 d .
C17 C 0.0777(7) 0.3494(17) 0.7398(5) 0.043(2) Uani 1 1 d .
C5 C 0.3953(8) 0.2642(19) 0.7948(7) 0.051(3) Uani 1 1 d .
H5 H 0.393(7) 0.10(2) 0.809(6) 0.061 Uiso 1 1 calc .
C15 C 0.1763(7) 0.437(2) 1.0365(6) 0.052(3) Uani 1 1 d .
H15 H 0.2001 0.5647 1.0676 0.062 Uiso 1 1 calc R
C3 C 0.4034(12) 0.165(2) 0.6397(8) 0.079(4) Uani 1 1 d .
H3A H 0.326(9) 0.20(3) 0.636(7) 0.094 Uiso 1 1 calc .
C16 C 0.1918(7) 0.4273(18) 0.9524(6) 0.044(2) Uani 1 1 d .
H16 H 0.2198 0.5545 0.9251 0.052 Uiso 1 1 calc R
C18 C -0.0268(9) 0.223(2) 0.7536(6) 0.061(3) Uani 1 1 d .
H18A H -0.0844 0.2963 0.7215 0.092 Uiso 1 1 calc R
H18B H -0.0419 0.2276 0.8120 0.092 Uiso 1 1 calc R
H18C H -0.0204 0.0648 0.7360 0.092 Uiso 1 1 calc R
C13 C 0.0943(7) 0.062(2) 1.0304(6) 0.053(3) Uani 1 1 d .
H13 H 0.0601 -0.0600 1.0563 0.063 Uiso 1 1 calc R
C4 C 0.4561(11) 0.2890(19) 0.7167(8) 0.073(4) Uani 1 1 d .
H4 H 0.454(9) 0.45(3) 0.703(7) 0.088 Uiso 1 1 calc .
C20 C 0.1578(10) 0.560(2) 0.6178(6) 0.063(3) Uani 1 1 d .
H20 H 0.1762 0.6813 0.6538 0.076 Uiso 1 1 calc R
C21 C 0.1861(10) 0.569(2) 0.5375(7) 0.068(3) Uani 1 1 d .
H21 H 0.2195 0.7022 0.5185 0.082 Uiso 1 1 calc R
C6 C 0.4477(7) 0.395(2) 0.8689(7) 0.063(3) Uani 1 1 d .
H6A H 0.4405 0.5596 0.8585 0.076 Uiso 1 1 calc R
H6B H 0.4090 0.3592 0.9187 0.076 Uiso 1 1 calc R
O1 O 0.1990(7) 0.4201(16) 0.4038(5) 0.083(2) Uani 1 1 d U
C9 C 0.5762(10) 0.230(3) 0.7367(9) 0.094(5) Uani 1 1 d .
H9A H 0.5825 0.0677 0.7510 0.113 Uiso 1 1 calc R
H9B H 0.6167 0.2570 0.6870 0.113 Uiso 1 1 calc R
C23 C 0.1104(9) 0.201(2) 0.5126(6) 0.068(3) Uani 1 1 d .
H23 H 0.0913 0.0804 0.4763 0.081 Uiso 1 1 calc R
C24 C 0.0832(9) 0.192(2) 0.5932(6) 0.065(3) Uani 1 1 d .
H24 H 0.0507 0.0578 0.6119 0.078 Uiso 1 1 calc R
C8 C 0.6243(9) 0.373(3) 0.8078(11) 0.097(5) Uani 1 1 d .
C22 C 0.1675(11) 0.392(2) 0.4836(6) 0.070(3) Uani 1 1 d .
C7 C 0.5597(10) 0.342(3) 0.8849(10) 0.084(4) Uani 1 1 d .
H7 H 0.564(10) 0.18(3) 0.900(8) 0.101 Uiso 1 1 calc .
C25 C 0.1861(15) 0.227(4) 0.3495(7) 0.120(6) Uani 1 1 d .
H25A H 0.1112 0.1877 0.3431 0.180 Uiso 1 1 calc R
H25B H 0.2255 0.0975 0.3729 0.180 Uiso 1 1 calc R
H25C H 0.2130 0.2647 0.2958 0.180 Uiso 1 1 calc R
C14 C 0.1241(8) 0.253(2) 1.0758(6) 0.059(3) Uani 1 1 d .
H14 H 0.1100 0.2624 1.1325 0.071 Uiso 1 1 calc R
C1 C 0.4520(16) 0.242(3) 0.5624(9) 0.152(9) Uani 1 1 d .
H1A H 0.4041 0.2078 0.5152 0.228 Uiso 1 1 calc R
H1B H 0.5191 0.1629 0.5562 0.228 Uiso 1 1 calc R
H1C H 0.4646 0.4059 0.5650 0.228 Uiso 1 1 calc R
C10 C 0.6086(11) 0.482(3) 0.9608(10) 0.111(6) Uani 1 1 d .
C2 C 0.4167(13) -0.098(2) 0.6482(9) 0.093(4) Uani 1 1 d .
H2A H 0.4918 -0.1349 0.6552 0.140 Uiso 1 1 calc R
H2B H 0.3870 -0.1717 0.5986 0.140 Uiso 1 1 calc R
H2C H 0.3796 -0.1507 0.6960 0.140 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'
N N 0.0061 0.0033 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 P1 O4 115.0(4)
O2 P1 C11 110.1(4)
O4 P1 C11 106.2(4)
O2 P1 C17 113.2(4)
O4 P1 C17 103.1(4)
C11 P1 C17 108.8(4)
C5 O4 P1 123.2(7)
C12 C11 C16 117.6(8)
C12 C11 P1 119.7(7)
C16 C11 P1 122.5(7)
C13 C12 C11 122.3(10)
C24 C19 C20 115.2(9)
C24 C19 C17 123.3(9)
C20 C19 C17 120.8(8)
O3 C17 C19 112.0(8)
O3 C17 C18 104.9(7)
C19 C17 C18 112.1(7)
O3 C17 P1 108.2(6)
C19 C17 P1 111.1(7)
C18 C17 P1 108.2(7)
O4 C5 C4 110.0(10)
O4 C5 C6 108.9(8)
C4 C5 C6 112.7(9)
C16 C15 C14 119.7(10)
C1 C3 C2 109.1(12)
C1 C3 C4 110.8(13)
C2 C3 C4 110.4(12)
C15 C16 C11 120.2(9)
C12 C13 C14 120.3(10)
C5 C4 C3 114.1(10)
C5 C4 C9 109.0(11)
C3 C4 C9 115.7(10)
C21 C20 C19 121.4(10)
C20 C21 C22 122.0(11)
C7 C6 C5 114.2(10)
C22 O1 C25 116.7(10)
C8 C9 C4 112.5(11)
C24 C23 C22 119.9(10)
C23 C24 C19 123.8(11)
C9 C8 C7 110.0(11)
C21 C22 O1 117.2(11)
C21 C22 C23 117.5(9)
O1 C22 C23 125.1(10)
C6 C7 C8 112.0(13)
C6 C7 C10 111.6(11)
C8 C7 C10 111.6(12)
C13 C14 C15 119.6(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O2 1.485(7)
P1 O4 1.552(7)
P1 C11 1.774(8)
P1 C17 1.825(10)
O3 C17 1.446(11)
O4 C5 1.441(13)
C11 C12 1.380(13)
C11 C16 1.410(13)
C12 C13 1.349(12)
C19 C24 1.360(14)
C19 C20 1.417(15)
C19 C17 1.498(13)
C17 C18 1.516(13)
C5 C4 1.494(14)
C5 C6 1.525(15)
C15 C16 1.367(12)
C15 C14 1.406(15)
C3 C1 1.468(16)
C3 C2 1.533(17)
C3 C4 1.54(2)
C13 C14 1.365(15)
C4 C9 1.551(19)
C20 C21 1.346(14)
C21 C22 1.351(16)
C6 C7 1.438(17)
O1 C22 1.359(11)
O1 C25 1.418(18)
C9 C8 1.51(2)
C23 C24 1.345(13)
C23 C22 1.403(17)
C8 C7 1.510(19)
C7 C10 1.56(2)
