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#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/80/4028055.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_4028055
loop_
_publ_author_name
'Yasuhiro Morisaki'
'Ryosuke Kato'
'Yoshiki Chujo'
_publ_contact_author_address
;
Department of Polymer Chemistry, Graduate School of Engineering,
Kyoto University,
;
_publ_contact_author_email       ' ymo_at_chujo.synchem.kyoto-u.ac.jp '
_publ_contact_author_fax         ' +81-75-383-2607 '
_publ_contact_author_name        ' Yasuhiro Morisaki '
_publ_contact_author_phone       ' +81-75-383-2610 '
_publ_section_title
;
 Synthesis of Enantiopure P-Stereogenic Diphosphacrowns using
 P-Stereogenic Secondary Phosphines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2769
_journal_page_last               2774
_journal_paper_doi               10.1021/jo302748x
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C20 H40 B2 O2 P2'
_chemical_formula_sum            'C20 H40 B2 O2 P2'
_chemical_formula_weight         396.08
_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                   10.8850(5)
_cell_length_b                   11.4534(5)
_cell_length_c                   18.6129(9)
_cell_measurement_reflns_used    15778
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      54.90
_cell_measurement_theta_min      6.77
_cell_volume                     2320.48(18)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'Yadokari-XG (Wakita, 2000)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, 2000)'
_computing_publication_material  'Yadokari-XG (Wakita, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'rigaku raxis rapid'
_diffrn_measurement_method       'oscillation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_sigmaI/netI    0.0590
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            21677
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.39
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.9613
_exptl_absorpt_correction_T_min  0.9247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.920
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         5274
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.188
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0554P)²+3.3129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1719
_reflns_number_gt                4149
_reflns_number_total             5274
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302748x_si_002.cif
_cod_data_source_block           no249
_cod_original_sg_symbol_Hall     p_2ac2ab
_cod_database_code               4028055
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
P1 P 0.31699(9) 1.16344(10) 0.92241(5) 0.0251(2) Uani 1 1 d .
C1 C 0.4760(4) 1.1449(4) 0.8929(2) 0.0314(10) Uani 1 1 d .
H1 H 0.4815 1.1710 0.8423 0.038 Uiso 1 1 calc R
H2 H 0.5281 1.1980 0.9218 0.038 Uiso 1 1 calc R
C2 C 0.5298(4) 1.0252(4) 0.8975(2) 0.0303(9) Uani 1 1 d .
H3 H 0.6184 1.0272 0.8857 0.036 Uiso 1 1 calc R
H4 H 0.5200 0.9935 0.9466 0.036 Uiso 1 1 calc R
O1 O 0.4643(2) 0.9539(3) 0.84641(16) 0.0292(6) Uani 1 1 d .
C3 C 0.4921(3) 0.8387(4) 0.8408(2) 0.0260(8) Uani 1 1 d .
C4 C 0.5917(4) 0.7839(4) 0.8722(2) 0.0290(9) Uani 1 1 d .
H5 H 0.6480 0.8276 0.9005 0.035 Uiso 1 1 calc R
C5 C 0.6094(4) 0.6641(4) 0.8621(2) 0.0368(11) Uani 1 1 d .
H6 H 0.6762 0.6258 0.8851 0.044 Uiso 1 1 calc R
C6 C 0.5301(4) 0.6011(5) 0.8190(2) 0.0385(11) Uani 1 1 d .
H7 H 0.5446 0.5203 0.8110 0.046 Uiso 1 1 calc R
C7 C 0.4286(4) 0.6554(4) 0.7870(2) 0.0316(9) Uani 1 1 d .
H8 H 0.3734 0.6118 0.7579 0.038 Uiso 1 1 calc R
C8 C 0.4100(4) 0.7730(4) 0.7983(2) 0.0266(9) Uani 1 1 d .
O2 O 0.3145(3) 0.8377(3) 0.77056(14) 0.0301(6) Uani 1 1 d .
C9 C 0.2090(4) 0.7758(4) 0.7424(2) 0.0306(10) Uani 1 1 d .
H9 H 0.1963 0.7018 0.7688 0.037 Uiso 1 1 calc R
H10 H 0.2207 0.7578 0.6909 0.037 Uiso 1 1 calc R
C10 C 0.0997(4) 0.8564(4) 0.7527(2) 0.0293(9) Uani 1 1 d .
H11 H 0.0286 0.8203 0.7281 0.035 Uiso 1 1 calc R
H12 H 0.1181 0.9302 0.7271 0.035 Uiso 1 1 calc R
P2 P 0.05026(9) 0.89487(10) 0.84428(5) 0.0245(2) Uani 1 1 d .
C11 C 0.1781(4) 0.9617(4) 0.8930(2) 0.0249(8) Uani 1 1 d .
H13 H 0.1538 0.9729 0.9438 0.030 Uiso 1 1 calc R
H14 H 0.2490 0.9076 0.8922 0.030 Uiso 1 1 calc R
C12 C 0.2179(3) 1.0795(3) 0.8617(2) 0.0241(9) Uani 1 1 d .
H15 H 0.1438 1.1262 0.8506 0.029 Uiso 1 1 calc R
H16 H 0.2624 1.0658 0.8160 0.029 Uiso 1 1 calc R
B1 B 0.2970(5) 1.1220(4) 1.0213(2) 0.0294(10) Uani 1 1 d .
H17 H 0.3269 1.0423 1.0289 0.044 Uiso 1 1 calc R
H18 H 0.2099 1.1265 1.0342 0.044 Uiso 1 1 calc R
H19 H 0.3441 1.1762 1.0514 0.044 Uiso 1 1 calc R
C13 C 0.2826(4) 1.3177(4) 0.9015(2) 0.0314(10) Uani 1 1 d .
C14 C 0.2874(4) 1.3420(4) 0.8205(2) 0.0341(10) Uani 1 1 d .
H20 H 0.3710 1.3284 0.8028 0.051 Uiso 1 1 calc R
H21 H 0.2642 1.4234 0.8115 0.051 Uiso 1 1 calc R
H22 H 0.2302 1.2899 0.7956 0.051 Uiso 1 1 calc R
C15 C 0.3729(5) 1.3985(5) 0.9408(3) 0.0474(13) Uani 1 1 d .
H23 H 0.3481 1.4800 0.9337 0.071 Uiso 1 1 calc R
H24 H 0.4558 1.3869 0.9217 0.071 Uiso 1 1 calc R
H25 H 0.3722 1.3804 0.9923 0.071 Uiso 1 1 calc R
C16 C 0.1509(5) 1.3435(5) 0.9289(3) 0.0483(13) Uani 1 1 d .
H26 H 0.0930 1.2892 0.9063 0.072 Uiso 1 1 calc R
H27 H 0.1284 1.4239 0.9164 0.072 Uiso 1 1 calc R
H28 H 0.1481 1.3339 0.9812 0.072 Uiso 1 1 calc R
B2 B -0.0868(4) 1.0010(5) 0.8370(3) 0.0336(11) Uani 1 1 d .
H29 H -0.0685 1.0612 0.8012 0.050 Uiso 1 1 calc R
H30 H -0.1012 1.0379 0.8838 0.050 Uiso 1 1 calc R
H31 H -0.1604 0.9578 0.8225 0.050 Uiso 1 1 calc R
C17 C 0.0165(4) 0.7598(4) 0.8955(2) 0.0267(9) Uani 1 1 d .
C18 C 0.1322(4) 0.6986(4) 0.9238(2) 0.0300(9) Uani 1 1 d .
H32 H 0.1085 0.6279 0.9500 0.045 Uiso 1 1 calc R
H33 H 0.1765 0.7514 0.9561 0.045 Uiso 1 1 calc R
H34 H 0.1853 0.6775 0.8833 0.045 Uiso 1 1 calc R
C19 C -0.0564(4) 0.6750(4) 0.8469(2) 0.0355(10) Uani 1 1 d .
H35 H -0.1297 0.7145 0.8284 0.053 Uiso 1 1 calc R
H36 H -0.0811 0.6064 0.8749 0.053 Uiso 1 1 calc R
H37 H -0.0045 0.6503 0.8066 0.053 Uiso 1 1 calc R
C20 C -0.0651(4) 0.7938(4) 0.9597(2) 0.0320(10) Uani 1 1 d .
H38 H -0.0210 0.8495 0.9903 0.048 Uiso 1 1 calc R
H39 H -0.0851 0.7239 0.9877 0.048 Uiso 1 1 calc R
H40 H -0.1410 0.8298 0.9421 0.048 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'
B B 0.0013 0.0007 '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
C1 P1 C12 108.10(19)
C1 P1 C13 103.9(2)
C12 P1 C13 104.62(19)
C1 P1 B1 111.6(2)
C12 P1 B1 113.33(19)
C13 P1 B1 114.6(2)
C2 C1 P1 117.4(3)
O1 C2 C1 106.8(3)
C3 O1 C2 119.4(3)
O1 C3 C4 125.7(4)
O1 C3 C8 114.8(3)
C4 C3 C8 119.5(4)
C3 C4 C5 119.8(4)
C6 C5 C4 120.3(4)
C5 C6 C7 120.5(5)
C8 C7 C6 119.0(4)
O2 C8 C7 125.4(4)
O2 C8 C3 113.7(3)
C7 C8 C3 120.9(4)
C8 O2 C9 118.2(3)
O2 C9 C10 106.2(3)
C9 C10 P2 119.4(3)
C11 P2 C10 109.67(18)
C11 P2 C17 104.17(18)
C10 P2 C17 109.5(2)
C11 P2 B2 111.1(2)
C10 P2 B2 108.2(2)
C17 P2 B2 114.1(2)
C12 C11 P2 113.3(3)
C11 C12 P1 113.2(3)
C14 C13 C15 109.7(4)
C14 C13 C16 108.6(4)
C15 C13 C16 108.6(4)
C14 C13 P1 112.0(3)
C15 C13 P1 110.3(3)
C16 C13 P1 107.5(3)
C18 C17 C20 108.8(3)
C18 C17 C19 109.6(4)
C20 C17 C19 108.5(3)
C18 C17 P2 113.3(3)
C20 C17 P2 107.6(3)
C19 C17 P2 109.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C1 1.828(4)
P1 C12 1.835(4)
P1 C13 1.847(5)
P1 B1 1.913(5)
C1 C2 1.493(6)
C2 O1 1.442(5)
O1 C3 1.358(5)
C3 C4 1.382(5)
C3 C8 1.411(6)
C4 C5 1.399(7)
C5 C6 1.382(7)
C6 C7 1.401(6)
C7 C8 1.379(6)
C8 O2 1.376(5)
O2 C9 1.448(5)
C9 C10 1.518(6)
C10 P2 1.841(4)
P2 C11 1.828(4)
P2 C17 1.854(4)
P2 B2 1.929(5)
C11 C12 1.533(5)
C13 C14 1.534(6)
C13 C15 1.536(6)
C13 C16 1.550(6)
C17 C18 1.534(6)
C17 C20 1.540(6)
C17 C19 1.546(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139092598
