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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/4/02/52/4025223.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_4025223
loop_
_publ_author_name
'Sampak Samanta'
'Sandun Perera'
'Cong-Gui Zhao'
_publ_contact_author_address
;
    Department of Chemistry,
    The University of Texas,
    One UTSA Circle, San Antonio,
    Texas 78249-0621, USA
;
_publ_contact_author_email
;
Edward.Tiekink@utsa.edu
;
_publ_contact_author_fax         ' 1 210 458 7428 '
_publ_contact_author_name        ' Dr ERT Tiekink '
_publ_contact_author_phone       ' 1 210 458 5469 '
_publ_section_title
;
 Organocatalytic Enantioselective Synthesis of Both Diastereomers of
 α-Hydroxyphosphinates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1101
_journal_page_last               1106
_journal_paper_doi               10.1021/jo9022099
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C18 H22 Br O5 P'
_chemical_formula_sum            'C18 H22 Br O5 P'
_chemical_formula_weight         429.24
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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
_cell_angle_beta                 104.79(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.140(2)
_cell_length_b                   5.7779(12)
_cell_length_c                   16.691(3)
_cell_measurement_reflns_used    2824
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.2
_cell_measurement_theta_min      2.5
_cell_volume                     945.5(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) & DIAMOND (Brandenburg, 2006)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  AFC12Κ/SATURN724
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_av_sigmaI/netI    0.058
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6979
_diffrn_reflns_theta_full        26.5
_diffrn_reflns_theta_max         26.5
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.283
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.37
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.015(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3568
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.048
_refine_ls_R_factor_gt           0.044
_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)+(0.0353P)²+0.386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.091
_refine_ls_wR_factor_ref         0.094
_reflns_number_gt                3382
_reflns_number_total             3568
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9022099_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4025223
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br14 Br 0.57412(4) -0.25929(15) 0.62623(3) 0.04821(16) Uani 1 1 d . . .
P2 P 0.00084(10) 0.0452(2) 0.76819(6) 0.0228(2) Uani 1 1 d . . .
O1 O 0.1397(3) 0.4301(5) 0.76143(18) 0.0293(6) Uani 1 1 d D . .
H1O H 0.098(4) 0.514(7) 0.788(2) 0.044 Uiso 1 1 d D . .
O1W O 0.0072(4) -0.2519(7) 0.97010(18) 0.0583(9) Uani 1 1 d D . .
H1W H 0.002(6) -0.255(9) 0.9191(7) 0.087 Uiso 1 1 d D . .
H2W H 0.009(7) -0.392(3) 0.984(3) 0.087 Uiso 1 1 d D . .
O2 O 0.0088(3) -0.1965(4) 0.80037(15) 0.0291(6) Uani 1 1 d . . .
O3 O 0.4175(3) 0.4060(6) 0.89220(18) 0.0380(7) Uani 1 1 d . . .
O21 O -0.0871(2) 0.2144(5) 0.80840(14) 0.0259(5) Uani 1 1 d . . .
C1 C 0.1642(3) 0.2055(7) 0.7962(2) 0.0220(8) Uani 1 1 d . . .
C2 C 0.2089(4) 0.2109(7) 0.8912(2) 0.0276(8) Uani 1 1 d . . .
H2A H 0.1347 0.2829 0.9113 0.033 Uiso 1 1 calc R . .
H2B H 0.2182 0.0491 0.9114 0.033 Uiso 1 1 calc R . .
C3 C 0.3397(4) 0.3364(6) 0.9309(2) 0.0283(9) Uani 1 1 d . . .
C4 C 0.3666(5) 0.3686(9) 1.0232(3) 0.0445(12) Uani 1 1 d . . .
H4A H 0.3941 0.2205 1.0511 0.067 Uiso 1 1 calc R . .
H4B H 0.2835 0.4240 1.0367 0.067 Uiso 1 1 calc R . .
H4C H 0.4398 0.4822 1.0419 0.067 Uiso 1 1 calc R . .
C11 C 0.2671(4) 0.0904(6) 0.7559(2) 0.0228(8) Uani 1 1 d . . .
C12 C 0.3013(4) 0.1955(7) 0.6892(2) 0.0309(9) Uani 1 1 d . . .
H12 H 0.2608 0.3397 0.6693 0.037 Uiso 1 1 calc R . .
C13 C 0.3937(4) 0.0940(7) 0.6509(2) 0.0296(9) Uani 1 1 d . . .
H13 H 0.4178 0.1684 0.6059 0.035 Uiso 1 1 calc R . .
C14 C 0.4496(4) -0.1171(7) 0.6798(2) 0.0297(9) Uani 1 1 d . . .
C15 C 0.4176(4) -0.2265(7) 0.7454(2) 0.0299(9) Uani 1 1 d . . .
H15 H 0.4573 -0.3718 0.7644 0.036 Uiso 1 1 calc R . .
C16 C 0.3267(4) -0.1221(7) 0.7834(2) 0.0262(8) Uani 1 1 d . . .
H16 H 0.3046 -0.1966 0.8290 0.031 Uiso 1 1 calc R . .
C21 C -0.0698(4) 0.0655(7) 0.6594(2) 0.0249(8) Uani 1 1 d . . .
C22 C -0.0543(4) -0.1151(7) 0.6068(2) 0.0303(9) Uani 1 1 d . . .
H22 H -0.0024 -0.2481 0.6286 0.036 Uiso 1 1 calc R . .
C23 C -0.1158(4) -0.0985(8) 0.5218(3) 0.0336(10) Uani 1 1 d . . .
H23 H -0.1061 -0.2214 0.4859 0.040 Uiso 1 1 calc R . .
C24 C -0.1898(4) 0.0934(7) 0.4901(3) 0.0367(10) Uani 1 1 d . . .
H24 H -0.2318 0.1019 0.4323 0.044 Uiso 1 1 calc R . .
C25 C -0.2041(4) 0.2751(8) 0.5410(2) 0.0389(10) Uani 1 1 d . . .
H25 H -0.2547 0.4085 0.5182 0.047 Uiso 1 1 calc R . .
C26 C -0.1447(4) 0.2630(8) 0.6256(2) 0.0302(8) Uani 1 1 d . . .
H26 H -0.1547 0.3878 0.6606 0.036 Uiso 1 1 calc R . .
C31 C -0.2290(4) 0.1602(8) 0.8061(3) 0.0384(10) Uani 1 1 d . . .
H31A H -0.2337 0.0163 0.8375 0.046 Uiso 1 1 calc R . .
H31B H -0.2827 0.1376 0.7482 0.046 Uiso 1 1 calc R . .
C32 C -0.2844(5) 0.3569(9) 0.8440(3) 0.0504(13) Uani 1 1 d . . .
H32A H -0.3797 0.3257 0.8431 0.076 Uiso 1 1 calc R . .
H32B H -0.2792 0.4983 0.8125 0.076 Uiso 1 1 calc R . .
H32C H -0.2309 0.3771 0.9014 0.076 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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
_geom_angle_publ_flag
O2 P2 O21 114.20(15) . . ?
O2 P2 C21 113.59(17) . . ?
O21 P2 C21 105.60(16) . . ?
O2 P2 C1 114.53(16) . . ?
O21 P2 C1 98.54(15) . . ?
C21 P2 C1 109.05(17) . . ?
C1 O1 H1O 112(3) . . ?
H1W O1W H2W 104.68(18) . . ?
C31 O21 P2 120.9(2) . . ?
O1 C1 C11 106.6(3) . . ?
O1 C1 C2 112.3(3) . . ?
C11 C1 C2 114.1(3) . . ?
O1 C1 P2 107.6(2) . . ?
C11 C1 P2 109.7(2) . . ?
C2 C1 P2 106.3(2) . . ?
C3 C2 C1 117.3(3) . . ?
C3 C2 H2A 108.0 . . ?
C1 C2 H2A 108.0 . . ?
C3 C2 H2B 108.0 . . ?
C1 C2 H2B 108.0 . . ?
H2A C2 H2B 107.2 . . ?
O3 C3 C2 123.1(3) . . ?
O3 C3 C4 122.2(4) . . ?
C2 C3 C4 114.7(4) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C12 C11 C16 118.3(3) . . ?
C12 C11 C1 120.0(3) . . ?
C16 C11 C1 121.7(3) . . ?
C11 C12 C13 121.3(4) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 118.5(4) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C13 C14 C15 121.8(4) . . ?
C13 C14 Br14 118.6(3) . . ?
C15 C14 Br14 119.6(3) . . ?
C14 C15 C16 119.0(4) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C15 C16 C11 121.2(4) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C22 C21 C26 119.3(3) . . ?
C22 C21 P2 120.8(3) . . ?
C26 C21 P2 119.9(3) . . ?
C21 C22 C23 119.5(4) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C24 C23 C22 120.4(4) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 120.7(4) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C24 C25 C26 120.1(4) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 119.9(4) . . ?
C25 C26 H26 120.1 . . ?
C21 C26 H26 120.1 . . ?
O21 C31 C32 107.6(4) . . ?
O21 C31 H31A 110.2 . . ?
C32 C31 H31A 110.2 . . ?
O21 C31 H31B 110.2 . . ?
C32 C31 H31B 110.2 . . ?
H31A C31 H31B 108.5 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br14 C14 1.909(4) . ?
P2 O2 1.491(2) . ?
P2 O21 1.584(3) . ?
P2 C21 1.778(4) . ?
P2 C1 1.850(4) . ?
O1 C1 1.418(5) . ?
O1 H1O 0.8400(10) . ?
O1W H1W 0.8400(10) . ?
O1W H2W 0.8400(11) . ?
O3 C3 1.209(5) . ?
O21 C31 1.464(5) . ?
C1 C11 1.531(5) . ?
C1 C2 1.534(4) . ?
C2 C3 1.508(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.506(5) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C11 C12 1.388(5) . ?
C11 C16 1.393(5) . ?
C12 C13 1.392(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.373(5) . ?
C15 C16 1.383(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C22 1.397(5) . ?
C21 C26 1.407(5) . ?
C22 C23 1.400(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.368(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.382(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.388(5) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.479(6) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 P2 O21 C31 -55.9(3) . . . . ?
C21 P2 O21 C31 69.7(3) . . . . ?
C1 P2 O21 C31 -177.7(3) . . . . ?
O2 P2 C1 O1 -179.9(2) . . . . ?
O21 P2 C1 O1 -58.3(2) . . . . ?
C21 P2 C1 O1 51.5(3) . . . . ?
O2 P2 C1 C11 64.5(3) . . . . ?
O21 P2 C1 C11 -173.9(2) . . . . ?
C21 P2 C1 C11 -64.1(3) . . . . ?
O2 P2 C1 C2 -59.4(3) . . . . ?
O21 P2 C1 C2 62.2(3) . . . . ?
C21 P2 C1 C2 172.1(2) . . . . ?
O1 C1 C2 C3 -61.6(4) . . . . ?
C11 C1 C2 C3 59.9(5) . . . . ?
P2 C1 C2 C3 -179.0(3) . . . . ?
C1 C2 C3 O3 -9.4(6) . . . . ?
C1 C2 C3 C4 170.7(4) . . . . ?
O1 C1 C11 C12 -9.3(4) . . . . ?
C2 C1 C11 C12 -133.8(4) . . . . ?
P2 C1 C11 C12 107.0(3) . . . . ?
O1 C1 C11 C16 171.9(3) . . . . ?
C2 C1 C11 C16 47.4(5) . . . . ?
P2 C1 C11 C16 -71.8(4) . . . . ?
C16 C11 C12 C13 -0.7(5) . . . . ?
C1 C11 C12 C13 -179.5(3) . . . . ?
C11 C12 C13 C14 1.1(6) . . . . ?
C12 C13 C14 C15 -0.8(5) . . . . ?
C12 C13 C14 Br14 179.0(3) . . . . ?
C13 C14 C15 C16 0.1(6) . . . . ?
Br14 C14 C15 C16 -179.7(3) . . . . ?
C14 C15 C16 C11 0.4(6) . . . . ?
C12 C11 C16 C15 -0.1(5) . . . . ?
C1 C11 C16 C15 178.8(3) . . . . ?
O2 P2 C21 C22 -29.9(4) . . . . ?
O21 P2 C21 C22 -155.8(3) . . . . ?
C1 P2 C21 C22 99.1(3) . . . . ?
O2 P2 C21 C26 148.7(3) . . . . ?
O21 P2 C21 C26 22.8(4) . . . . ?
C1 P2 C21 C26 -82.3(3) . . . . ?
C26 C21 C22 C23 -1.3(6) . . . . ?
P2 C21 C22 C23 177.3(3) . . . . ?
C21 C22 C23 C24 0.5(6) . . . . ?
C22 C23 C24 C25 0.6(7) . . . . ?
C23 C24 C25 C26 -0.9(7) . . . . ?
C24 C25 C26 C21 0.1(6) . . . . ?
C22 C21 C26 C25 1.0(6) . . . . ?
P2 C21 C26 C25 -177.6(3) . . . . ?
P2 O21 C31 C32 -176.7(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139078446
