#------------------------------------------------------------------------------
#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/41/4034124.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_4034124
loop_
_publ_author_name
'Zhang, Yu'
'Nie, Shao-Zhen'
'Ye, Jing-Jing'
'Wang, Ji-Ping'
'Zhou, Meng-Meng'
'Zhao, Chang-Qiu'
'Li, Qiang'
_publ_section_title
;
 Functional Phosphine Derivatives Having Stationary and Flexible
 Chiralities: Their Preparation and Chirality Controlling.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8423
_journal_page_last               8439
_journal_paper_doi               10.1021/acs.joc.9b00346
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration R
_chemical_formula_sum            'C24 H36 B O P'
_chemical_formula_weight         382.31
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_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                   9.0034(7)
_cell_length_b                   15.0541(13)
_cell_length_c                   17.4228(14)
_cell_measurement_reflns_used    2609
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.241
_cell_measurement_theta_min      2.338
_cell_volume                     2361.5(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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  0.0548
_diffrn_reflns_av_sigmaI/netI    0.0635
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11928
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.9594
_exptl_absorpt_correction_T_min  0.9452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.075
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4171
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0483
_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)+(0.0452P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1093
_reflns_number_gt                2723
_reflns_number_total             4171
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b00346_si_006.cif
_cod_data_source_block           180522f
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P2(1)2(1)2(1) '
_cod_database_code               4034124
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 0.43120(8) 0.66631(5) 0.22559(4) 0.0465(2) Uani 1 1 d .
O1 O 0.2057(3) 0.60198(17) 0.44528(12) 0.0892(9) Uani 1 1 d .
B1 B 0.5208(4) 0.5827(3) 0.1582(2) 0.0729(13) Uani 1 1 d .
H1A H 0.5015 0.5236 0.1764 0.109 Uiso 1 1 calc R
H1B H 0.6261 0.5927 0.1566 0.109 Uiso 1 1 calc R
H1C H 0.4800 0.5896 0.1077 0.109 Uiso 1 1 calc R
C1 C 0.2346(3) 0.63960(17) 0.23814(15) 0.0440(7) Uani 1 1 d .
C2 C 0.1718(4) 0.5883(2) 0.18076(18) 0.0594(9) Uani 1 1 d .
H2 H 0.2280 0.5751 0.1374 0.071 Uiso 1 1 calc R
C3 C 0.0291(4) 0.5560(2) 0.1856(2) 0.0703(10) Uani 1 1 d .
H3 H -0.0102 0.5218 0.1460 0.084 Uiso 1 1 calc R
C4 C -0.0543(4) 0.5747(3) 0.2491(2) 0.0749(11) Uani 1 1 d .
H4 H -0.1501 0.5522 0.2537 0.090 Uiso 1 1 calc R
C5 C 0.0044(4) 0.6268(3) 0.3058(2) 0.0715(11) Uani 1 1 d .
H5 H -0.0531 0.6388 0.3489 0.086 Uiso 1 1 calc R
C6 C 0.1468(3) 0.6626(2) 0.30161(16) 0.0498(7) Uani 1 1 d .
C7 C 0.1966(3) 0.7246(2) 0.36375(17) 0.0534(8) Uani 1 1 d .
C8 C 0.2225(4) 0.6919(3) 0.43713(19) 0.0712(10) Uani 1 1 d .
C9 C 0.2678(5) 0.7482(3) 0.4953(2) 0.0978(15) Uani 1 1 d .
H9 H 0.2862 0.7261 0.5442 0.117 Uiso 1 1 calc R
C10 C 0.2853(5) 0.8366(3) 0.4802(2) 0.1092(15) Uani 1 1 d .
H10 H 0.3166 0.8744 0.5192 0.131 Uiso 1 1 calc R
C11 C 0.2575(4) 0.8711(3) 0.4082(2) 0.0872(12) Uani 1 1 d .
H11 H 0.2691 0.9314 0.3985 0.105 Uiso 1 1 calc R
C12 C 0.2119(3) 0.8136(2) 0.35082(18) 0.0590(9) Uani 1 1 d .
H12 H 0.1912 0.8362 0.3023 0.071 Uiso 1 1 calc R
C13 C 0.2182(6) 0.5642(3) 0.5194(2) 0.1271(19) Uani 1 1 d .
H13A H 0.3152 0.5763 0.5398 0.191 Uiso 1 1 calc R
H13B H 0.2036 0.5011 0.5162 0.191 Uiso 1 1 calc R
H13C H 0.1442 0.5896 0.5525 0.191 Uiso 1 1 calc R
C14 C 0.4450(3) 0.78259(18) 0.19139(16) 0.0451(7) Uani 1 1 d .
H14 H 0.4332 0.8219 0.2358 0.054 Uiso 1 1 calc R
C15 C 0.5953(3) 0.8036(2) 0.15352(18) 0.0547(8) Uani 1 1 d .
H15 H 0.6030 0.7653 0.1082 0.066 Uiso 1 1 calc R
C16 C 0.5915(4) 0.9000(2) 0.1239(2) 0.0791(11) Uani 1 1 d .
H16A H 0.5814 0.9401 0.1672 0.095 Uiso 1 1 calc R
H16B H 0.6848 0.9133 0.0985 0.095 Uiso 1 1 calc R
C17 C 0.4650(4) 0.9157(3) 0.0684(2) 0.0825(11) Uani 1 1 d .
H17A H 0.4662 0.9773 0.0521 0.099 Uiso 1 1 calc R
H17B H 0.4791 0.8788 0.0234 0.099 Uiso 1 1 calc R
C18 C 0.3173(4) 0.8950(2) 0.1036(2) 0.0724(10) Uani 1 1 d .
H18 H 0.3023 0.9360 0.1467 0.087 Uiso 1 1 calc R
C19 C 0.3179(4) 0.8011(2) 0.13562(18) 0.0596(9) Uani 1 1 d .
H19A H 0.3243 0.7595 0.0932 0.072 Uiso 1 1 calc R
H19B H 0.2244 0.7905 0.1618 0.072 Uiso 1 1 calc R
C20 C 0.7327(4) 0.7856(2) 0.2024(2) 0.0699(10) Uani 1 1 d .
H20 H 0.7240 0.7246 0.2215 0.084 Uiso 1 1 calc R
C21 C 0.8746(4) 0.7900(3) 0.1547(3) 0.1276(19) Uani 1 1 d .
H21A H 0.8614 0.7568 0.1082 0.191 Uiso 1 1 calc R
H21B H 0.9554 0.7652 0.1835 0.191 Uiso 1 1 calc R
H21C H 0.8963 0.8508 0.1424 0.191 Uiso 1 1 calc R
C22 C 0.7451(4) 0.8464(3) 0.2730(2) 0.1081(14) Uani 1 1 d .
H22A H 0.7673 0.9058 0.2566 0.162 Uiso 1 1 calc R
H22B H 0.8231 0.8252 0.3058 0.162 Uiso 1 1 calc R
H22C H 0.6528 0.8460 0.3005 0.162 Uiso 1 1 calc R
C23 C 0.1892(5) 0.9085(3) 0.0472(2) 0.1210(18) Uani 1 1 d .
H23A H 0.1930 0.9678 0.0270 0.181 Uiso 1 1 calc R
H23B H 0.0965 0.8997 0.0733 0.181 Uiso 1 1 calc R
H23C H 0.1978 0.8666 0.0060 0.181 Uiso 1 1 calc R
C24 C 0.5150(3) 0.6580(2) 0.31979(16) 0.0613(9) Uani 1 1 d .
H24A H 0.4951 0.7113 0.3483 0.092 Uiso 1 1 calc R
H24B H 0.6204 0.6505 0.3145 0.092 Uiso 1 1 calc R
H24C H 0.4741 0.6079 0.3465 0.092 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'
B B 0.0013 0.0007 '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
C24 P1 C1 106.26(14)
C24 P1 C14 109.18(15)
C1 P1 C14 108.13(13)
C24 P1 B1 109.69(18)
C1 P1 B1 109.83(14)
C14 P1 B1 113.48(17)
C8 O1 C13 118.9(3)
C2 C1 C6 118.5(3)
C2 C1 P1 115.6(2)
C6 C1 P1 125.8(2)
C3 C2 C1 122.3(3)
C4 C3 C2 119.3(3)
C3 C4 C5 119.4(3)
C4 C5 C6 122.7(3)
C5 C6 C1 117.6(3)
C5 C6 C7 118.6(3)
C1 C6 C7 123.7(3)
C12 C7 C8 118.8(3)
C12 C7 C6 121.5(3)
C8 C7 C6 119.6(3)
O1 C8 C9 124.2(3)
O1 C8 C7 115.3(3)
C9 C8 C7 120.4(4)
C10 C9 C8 119.3(4)
C9 C10 C11 121.4(4)
C10 C11 C12 118.4(4)
C7 C12 C11 121.6(3)
C19 C14 C15 110.4(2)
C19 C14 P1 109.06(19)
C15 C14 P1 113.1(2)
C20 C15 C14 115.9(2)
C20 C15 C16 111.8(3)
C14 C15 C16 108.6(3)
C17 C16 C15 112.2(3)
C18 C17 C16 112.0(3)
C17 C18 C19 109.9(3)
C17 C18 C23 112.3(3)
C19 C18 C23 111.2(3)
C18 C19 C14 113.9(3)
C21 C20 C15 111.6(3)
C21 C20 C22 110.4(3)
C15 C20 C22 113.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C24 1.811(3)
P1 C1 1.829(3)
P1 C14 1.853(3)
P1 B1 1.900(4)
O1 C8 1.370(4)
O1 C13 1.416(4)
C1 C2 1.384(4)
C1 C6 1.403(3)
C2 C3 1.376(4)
C3 C4 1.366(4)
C4 C5 1.368(4)
C5 C6 1.393(4)
C6 C7 1.498(4)
C7 C12 1.365(4)
C7 C8 1.390(4)
C8 C9 1.382(5)
C9 C10 1.366(6)
C10 C11 1.379(5)
C11 C12 1.385(4)
C14 C19 1.527(4)
C14 C15 1.538(4)
C15 C20 1.526(4)
C15 C16 1.540(4)
C16 C17 1.513(4)
C17 C18 1.497(4)
C18 C19 1.520(4)
C18 C23 1.528(5)
C20 C21 1.525(5)
C20 C22 1.537(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168328072
