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#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/58/1505890.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_1505890
loop_
_publ_author_name
'Du, Da-Ming'
'Fang, Tao'
'Xu, Jiaxi'
'Zhang, Shi-Wei'
_publ_section_title
;
 Structurally well-defined, recoverable C3-symmetric tris(beta-hydroxy
 phosphoramide)-catalyzed enantioselective borane reduction of ketones.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1327
_journal_page_last               1330
_journal_paper_doi               10.1021/ol0600584
_journal_volume                  8
_journal_year                    2006
_chemical_compound_source        synthesis
_chemical_formula_sum            'C51 H54 N3 O4 P'
_chemical_formula_weight         803.94
_chemical_melting_point          533
_chemical_name_common            'tisphosphoramide 1d'
_space_group_IT_number           173
_symmetry_cell_setting           trigonal
_symmetry_Int_Tables_number      173
_symmetry_space_group_name_Hall  'P 6c'
_symmetry_space_group_name_H-M   'P 63'
_atom_sites_solution_hydrogens   'geom or difmap'
_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                120.00
_cell_formula_units_Z            2
_cell_length_a                   16.645(2)
_cell_length_b                   16.645(2)
_cell_length_c                   9.0395(18)
_cell_measurement_reflns_used    12217
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.45
_cell_volume                     2168.9(6)
_computing_cell_refinement       Rapid-AUTO
_computing_data_collection       'Rapid-AUTO (Rigaku,2000)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC,2000)'
_computing_molecular_graphics    'Siemens SHELXTL V4.2,(Sheldrick,1990)'
_computing_publication_material  SHELXL-97,(Sheldrick,1997)
_computing_structure_refinement  SHELXL-97,(Sheldrick,1997)
_computing_structure_solution    SHELXS-97,(Sheldrick,1997)
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku RAXIS RAPID IP'
_diffrn_measurement_method       Ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_sigmaI/netI    0.0630
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12217
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.45
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Rigaku 2000'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
                                  HIGASHI, T. (1995). Abscor-Empirical
                                  Absorption Correction based on Fourier
                                  Series Approximation.
                                  Rigaku Corporation,Tokyo,Japan.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_recrystallization_method 'ethyl acetate-petroleum ether'
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.35(16)
_refine_ls_extinction_coef       0.0200(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.798
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         1371
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.798
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0305
_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)+(0.0290P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0645
_reflns_number_gt                914
_reflns_number_total             1371
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0600584si20060131_041240.cif
_cod_data_source_block           1d
_cod_database_code               1505890
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
P1 P 0.3333 0.6667 0.18267(15) 0.0434(4) Uani 1 3 d S
O1 O 0.23414(15) 0.75436(15) -0.0584(2) 0.0597(7) Uani 1 1 d .
HO1 H 0.2642(19) 0.7207(19) -0.038(4) 0.075(11) Uiso 1 1 d .
O2 O 0.3333 0.6667 0.0165(4) 0.0428(8) Uani 1 3 d S
N1 N 0.25774(14) 0.69312(14) 0.2474(2) 0.0440(6) Uani 1 1 d .
C1 C 0.02634(19) 0.6769(2) 0.1794(4) 0.0627(8) Uani 1 1 d .
H1 H 0.0341 0.7332 0.2129 0.075 Uiso 1 1 calc R
C2 C -0.0548(2) 0.5954(3) 0.2128(4) 0.0780(11) Uani 1 1 d .
H2 H -0.1013 0.5971 0.2675 0.094 Uiso 1 1 calc R
C3 C -0.0661(2) 0.5117(2) 0.1640(4) 0.0793(11) Uani 1 1 d .
H3 H -0.1190 0.4565 0.1898 0.095 Uiso 1 1 calc R
C4 C 0.0006(3) 0.5100(2) 0.0778(5) 0.0740(10) Uani 1 1 d .
H4 H -0.0084 0.4538 0.0415 0.089 Uiso 1 1 calc R
C5 C 0.08110(19) 0.5910(2) 0.0444(4) 0.0598(9) Uani 1 1 d .
H5 H 0.1259 0.5887 -0.0140 0.072 Uiso 1 1 calc R
C6 C 0.09645(18) 0.67589(18) 0.0965(4) 0.0493(7) Uani 1 1 d .
C7 C 0.19073(18) 0.76343(18) 0.0730(4) 0.0472(7) Uani 1 1 d .
C8 C 0.18102(19) 0.8488(2) 0.0412(4) 0.0576(9) Uani 1 1 d .
C9 C 0.1131(2) 0.8390(2) -0.0604(5) 0.0770(10) Uani 1 1 d .
H9 H 0.0733 0.7812 -0.1015 0.092 Uiso 1 1 calc R
C10 C 0.1048(3) 0.9151(3) -0.1002(5) 0.0961(14) Uani 1 1 d .
H10 H 0.0593 0.9078 -0.1674 0.115 Uiso 1 1 calc R
C11 C 0.1633(3) 1.0011(3) -0.0409(6) 0.0982(15) Uani 1 1 d .
H11 H 0.1571 1.0519 -0.0669 0.118 Uiso 1 1 calc R
C12 C 0.2305(3) 1.0113(2) 0.0568(5) 0.0827(12) Uani 1 1 d .
H12 H 0.2701 1.0693 0.0972 0.099 Uiso 1 1 calc R
C13 C 0.2407(2) 0.93631(19) 0.0964(4) 0.0654(9) Uani 1 1 d .
H13 H 0.2880 0.9450 0.1607 0.079 Uiso 1 1 calc R
C14 C 0.25443(18) 0.77794(18) 0.2078(4) 0.0479(8) Uani 1 1 d .
H14 H 0.3175 0.8266 0.1822 0.058 Uiso 1 1 calc R
C15 C 0.2272(2) 0.8057(2) 0.3549(3) 0.0550(8) Uani 1 1 d .
H15A H 0.2806 0.8595 0.3972 0.066 Uiso 1 1 calc R
H15B H 0.1790 0.8211 0.3375 0.066 Uiso 1 1 calc R
C16 C 0.1929(2) 0.7246(2) 0.4585(4) 0.0746(10) Uani 1 1 d .
H16A H 0.2298 0.7427 0.5482 0.089 Uiso 1 1 calc R
H16B H 0.1288 0.7028 0.4851 0.089 Uiso 1 1 calc R
C17 C 0.20097(19) 0.64946(19) 0.3804(3) 0.0562(8) Uani 1 1 d .
H17A H 0.2308 0.6250 0.4436 0.067 Uiso 1 1 calc R
H17B H 0.1401 0.5991 0.3528 0.067 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O2 P1 N1 110.98(9) . .
O2 P1 N1 110.98(9) . 3_565
N1 P1 N1 107.92(9) . 3_565
O2 P1 N1 110.98(9) . 2_665
N1 P1 N1 107.92(9) . 2_665
N1 P1 N1 107.92(9) 3_565 2_665
C7 O1 HO1 110(2) . .
C17 N1 C14 110.2(2) . .
C17 N1 P1 123.25(17) . .
C14 N1 P1 124.70(17) . .
C2 C1 C6 121.1(3) . .
C2 C1 H1 119.4 . .
C6 C1 H1 119.4 . .
C3 C2 C1 119.4(3) . .
C3 C2 H2 120.3 . .
C1 C2 H2 120.3 . .
C4 C3 C2 120.0(3) . .
C4 C3 H3 120.0 . .
C2 C3 H3 120.0 . .
C3 C4 C5 120.5(3) . .
C3 C4 H4 119.8 . .
C5 C4 H4 119.8 . .
C4 C5 C6 121.1(3) . .
C4 C5 H5 119.5 . .
C6 C5 H5 119.5 . .
C5 C6 C1 117.8(3) . .
C5 C6 C7 120.1(3) . .
C1 C6 C7 121.9(3) . .
O1 C7 C6 110.2(2) . .
O1 C7 C8 103.5(2) . .
C6 C7 C8 112.0(2) . .
O1 C7 C14 109.0(2) . .
C6 C7 C14 109.5(2) . .
C8 C7 C14 112.5(2) . .
C13 C8 C9 118.1(3) . .
C13 C8 C7 123.8(3) . .
C9 C8 C7 117.9(3) . .
C10 C9 C8 120.4(3) . .
C10 C9 H9 119.8 . .
C8 C9 H9 119.8 . .
C11 C10 C9 120.5(4) . .
C11 C10 H10 119.7 . .
C9 C10 H10 119.7 . .
C12 C11 C10 119.3(3) . .
C12 C11 H11 120.4 . .
C10 C11 H11 120.4 . .
C11 C12 C13 121.0(4) . .
C11 C12 H12 119.5 . .
C13 C12 H12 119.5 . .
C8 C13 C12 120.6(3) . .
C8 C13 H13 119.7 . .
C12 C13 H13 119.7 . .
N1 C14 C15 103.4(2) . .
N1 C14 C7 112.9(2) . .
C15 C14 C7 116.2(2) . .
N1 C14 H14 108.0 . .
C15 C14 H14 108.0 . .
C7 C14 H14 108.0 . .
C16 C15 C14 107.7(2) . .
C16 C15 H15A 110.2 . .
C14 C15 H15A 110.2 . .
C16 C15 H15B 110.2 . .
C14 C15 H15B 110.2 . .
H15A C15 H15B 108.5 . .
C17 C16 C15 107.7(3) . .
C17 C16 H16A 110.2 . .
C15 C16 H16A 110.2 . .
C17 C16 H16B 110.2 . .
C15 C16 H16B 110.2 . .
H16A C16 H16B 108.5 . .
N1 C17 C16 106.0(2) . .
N1 C17 H17A 110.5 . .
C16 C17 H17A 110.5 . .
N1 C17 H17B 110.5 . .
C16 C17 H17B 110.5 . .
H17A C17 H17B 108.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 O2 1.502(4) .
P1 N1 1.635(2) .
P1 N1 1.635(2) 3_565
P1 N1 1.635(2) 2_665
O1 C7 1.437(3) .
O1 HO1 0.94(3) .
N1 C17 1.476(3) .
N1 C14 1.484(3) .
C1 C2 1.387(4) .
C1 C6 1.394(4) .
C1 H1 0.9300 .
C2 C3 1.382(4) .
C2 H2 0.9300 .
C3 C4 1.368(5) .
C3 H3 0.9300 .
C4 C5 1.377(4) .
C4 H4 0.9300 .
C5 C6 1.387(4) .
C5 H5 0.9300 .
C6 C7 1.531(3) .
C7 C8 1.535(4) .
C7 C14 1.553(4) .
C8 C13 1.383(4) .
C8 C9 1.402(4) .
C9 C10 1.388(4) .
C9 H9 0.9300 .
C10 C11 1.376(5) .
C10 H10 0.9300 .
C11 C12 1.368(5) .
C11 H11 0.9300 .
C12 C13 1.387(4) .
C12 H12 0.9300 .
C13 H13 0.9300 .
C14 C15 1.548(4) .
C14 H14 0.9800 .
C15 C16 1.501(4) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C17 1.500(4) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 HO1 O2 0.94(3) 1.85(3) 2.779(3) 173(3)
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
O2 P1 N1 C17 142.31(18) .
N1 P1 N1 C17 -95.89(16) 3_565
N1 P1 N1 C17 20.5(2) 2_665
O2 P1 N1 C14 -54.5(2) .
N1 P1 N1 C14 67.3(3) 3_565
N1 P1 N1 C14 -176.3(2) 2_665
C6 C1 C2 C3 0.5(5) .
C1 C2 C3 C4 -3.0(5) .
C2 C3 C4 C5 2.9(6) .
C3 C4 C5 C6 -0.3(5) .
C4 C5 C6 C1 -2.2(5) .
C4 C5 C6 C7 173.0(3) .
C2 C1 C6 C5 2.0(5) .
C2 C1 C6 C7 -173.0(3) .
C5 C6 C7 O1 28.4(4) .
C1 C6 C7 O1 -156.6(3) .
C5 C6 C7 C8 143.0(3) .
C1 C6 C7 C8 -42.0(4) .
C5 C6 C7 C14 -91.4(3) .
C1 C6 C7 C14 83.5(3) .
O1 C7 C8 C13 -100.4(3) .
C6 C7 C8 C13 141.0(3) .
C14 C7 C8 C13 17.1(4) .
O1 C7 C8 C9 73.5(3) .
C6 C7 C8 C9 -45.2(4) .
C14 C7 C8 C9 -169.1(3) .
C13 C8 C9 C10 -1.9(5) .
C7 C8 C9 C10 -176.1(3) .
C8 C9 C10 C11 0.2(6) .
C9 C10 C11 C12 0.7(6) .
C10 C11 C12 C13 0.1(6) .
C9 C8 C13 C12 2.8(5) .
C7 C8 C13 C12 176.6(3) .
C11 C12 C13 C8 -1.9(5) .
C17 N1 C14 C15 22.4(3) .
P1 N1 C14 C15 -142.6(2) .
C17 N1 C14 C7 -104.0(3) .
P1 N1 C14 C7 91.0(3) .
O1 C7 C14 N1 -70.8(3) .
C6 C7 C14 N1 49.8(3) .
C8 C7 C14 N1 175.0(2) .
O1 C7 C14 C15 170.0(2) .
C6 C7 C14 C15 -69.5(3) .
C8 C7 C14 C15 55.8(3) .
N1 C14 C15 C16 -14.3(3) .
C7 C14 C15 C16 110.0(3) .
C14 C15 C16 C17 1.6(4) .
C14 N1 C17 C16 -22.0(3) .
P1 N1 C17 C16 143.3(2) .
C15 C16 C17 N1 11.9(3) .
