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#$Date: 2024-03-04 22:39:24 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290251 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/96/7159669.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_7159669
loop_
_publ_author_name
'Tatarinov, Dmitry A.'
'Mikulenkova, Elina A.'
'Litvinov, Igor A.'
'Khayarov, Khasan R.'
'Mironov, Vladimir F.'
_publ_section_title
;
 Divergent synthesis of benzoxaphospholenes and phosphacoumarins via the
 reaction of 2-alkenylphenols with phosphorus(iii/v) chlorides
;
_journal_issue                   8
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              1629
_journal_page_last               1633
_journal_paper_doi               10.1039/D3OB01718D
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C28 H21 Cl2 O3 P'
_chemical_formula_sum            'C28 H21 Cl2 O3 P'
_chemical_formula_weight         507.32
_chemical_melting_point          508
_chemical_name_systematic
'4-(4-chlorophenyl)-2-(1-(4-chlorophenyl)-1-(2-hydroxyphenyl)ethyl)benzo[e][1,2]oxaphosphinine 2-oxide '
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-10-07 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.346(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4101(5)
_cell_length_b                   18.7328(7)
_cell_length_c                   11.6060(4)
_cell_measurement_reflns_used    9754
_cell_measurement_temperature    162(2)
_cell_measurement_theta_max      30.19
_cell_measurement_theta_min      2.17
_cell_volume                     2354.62(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      162(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0863
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            90603
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         2.145
_diffrn_source                   'I\mS DIAMOND'
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5708
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_description       plate
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         6826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.1251
_refine_ls_R_factor_gt           0.1086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0061P)²+12.2724P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2217
_refine_ls_wR_factor_ref         0.2281
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5442
_reflns_number_total             6826
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01718d2.cif
_cod_data_source_block           shelx_CCDC5
_cod_depositor_comments
'Adding full bibliography for 7159664--7159669.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7159669
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C3 C 0.7077(4) 0.6467(2) 0.5865(4) 0.0361(9) Uani 1 1 d . . . . .
H3 H 0.783668 0.637489 0.648217 0.043 Uiso 1 1 calc R U . . .
C4 C 0.7014(4) 0.6378(2) 0.4692(4) 0.0330(9) Uani 1 1 d . . . . .
C4A C 0.5882(4) 0.6503(2) 0.3675(4) 0.0336(9) Uani 1 1 d . . . . .
C5 C 0.5864(4) 0.6491(3) 0.2470(5) 0.0408(10) Uani 1 1 d . . . . .
H5 H 0.660643 0.639123 0.229527 0.049 Uiso 1 1 calc R U . . .
C6 C 0.4801(5) 0.6618(3) 0.1525(5) 0.0487(12) Uani 1 1 d . . . . .
H6 H 0.481186 0.660881 0.071040 0.058 Uiso 1 1 calc R U . . .
C7 C 0.3711(5) 0.6762(3) 0.1776(5) 0.0528(14) Uani 1 1 d . . . . .
H7 H 0.297088 0.684133 0.112691 0.063 Uiso 1 1 calc R U . . .
C8 C 0.3694(4) 0.6788(3) 0.2936(5) 0.0460(12) Uani 1 1 d . . . . .
H8 H 0.294603 0.689114 0.309891 0.055 Uiso 1 1 calc R U . . .
C8A C 0.4772(4) 0.6665(2) 0.3887(5) 0.0377(10) Uani 1 1 d . . . . .
C9 C 0.5434(4) 0.6051(2) 0.7237(4) 0.0301(8) Uani 1 1 d . . . . .
C10 C 0.5160(4) 0.5360(3) 0.6477(4) 0.0376(10) Uani 1 1 d . . . . .
H10A H 0.508512 0.495981 0.699360 0.056 Uiso 1 1 calc R U . . .
H10B H 0.583542 0.526521 0.614496 0.056 Uiso 1 1 calc R U . . .
H10C H 0.438569 0.541487 0.580976 0.056 Uiso 1 1 calc R U . . .
C11 C 0.6596(4) 0.5984(2) 0.8351(4) 0.0321(9) Uani 1 1 d . . . . .
C12 C 0.6957(5) 0.6519(3) 0.9241(5) 0.0444(12) Uani 1 1 d . . . . .
C13 C 0.8013(5) 0.6422(4) 1.0239(5) 0.0578(16) Uani 1 1 d . . . . .
H13 H 0.824244 0.678255 1.084446 0.069 Uiso 1 1 calc R U . . .
C14 C 0.8722(5) 0.5826(4) 1.0370(6) 0.0649(18) Uani 1 1 d . . . . .
H14 H 0.943508 0.577134 1.105842 0.078 Uiso 1 1 calc R U . . .
C15 C 0.8395(5) 0.5302(3) 0.9493(5) 0.0524(14) Uani 1 1 d . . . . .
H15 H 0.889440 0.488797 0.956538 0.063 Uiso 1 1 calc R U . . .
C16 C 0.7347(4) 0.5379(3) 0.8516(4) 0.0381(10) Uani 1 1 d . . . . .
H16 H 0.712310 0.500755 0.792989 0.046 Uiso 1 1 calc R U . . .
C17 C 0.4290(4) 0.6206(2) 0.7620(4) 0.0331(9) Uani 1 1 d . . . . .
C18 C 0.3419(5) 0.6722(3) 0.7083(6) 0.0544(15) Uani 1 1 d . . . . .
H18 H 0.354851 0.702202 0.647327 0.065 Uiso 1 1 calc R U . . .
C19 C 0.2362(5) 0.6811(3) 0.7417(6) 0.0580(15) Uani 1 1 d . . . . .
H19 H 0.178346 0.717525 0.705793 0.070 Uiso 1 1 calc R U . . .
C20 C 0.2166(4) 0.6362(3) 0.8276(5) 0.0469(12) Uani 1 1 d . . . . .
C21 C 0.2996(5) 0.5839(3) 0.8811(5) 0.0493(13) Uani 1 1 d . . . . .
H21 H 0.285025 0.553405 0.940570 0.059 Uiso 1 1 calc R U . . .
C22 C 0.4059(4) 0.5760(3) 0.8475(4) 0.0395(10) Uani 1 1 d . . . . .
H22 H 0.463356 0.539388 0.883711 0.047 Uiso 1 1 calc R U . . .
C23 C 0.8150(4) 0.6150(2) 0.4412(4) 0.0324(9) Uani 1 1 d . . . . .
C24 C 0.9210(4) 0.6560(3) 0.4798(5) 0.0425(11) Uani 1 1 d . . . . .
H24 H 0.921485 0.698697 0.524152 0.051 Uiso 1 1 calc R U . . .
C25 C 1.0266(4) 0.6351(3) 0.4539(5) 0.0442(12) Uani 1 1 d . . . . .
H25 H 1.099000 0.663676 0.479169 0.053 Uiso 1 1 calc R U . . .
C26 C 1.0258(4) 0.5732(3) 0.3922(5) 0.0389(10) Uani 1 1 d . . . . .
C27 C 0.9227(4) 0.5304(3) 0.3526(5) 0.0410(11) Uani 1 1 d . . . . .
H27 H 0.923577 0.487679 0.308887 0.049 Uiso 1 1 calc R U . . .
C28 C 0.8174(4) 0.5520(3) 0.3789(5) 0.0396(10) Uani 1 1 d . . . . .
H28 H 0.745463 0.523068 0.353721 0.048 Uiso 1 1 calc R U . . .
Cl20 Cl 0.08254(13) 0.64589(9) 0.86779(17) 0.0666(5) Uani 1 1 d . . . . .
Cl26 Cl 1.15839(13) 0.54732(9) 0.35923(16) 0.0616(4) Uani 1 1 d . . . . .
O1 O 0.4676(3) 0.6697(2) 0.5047(4) 0.0519(10) Uani 1 1 d . . . . .
O2 O 0.5894(3) 0.74571(18) 0.6870(4) 0.0510(10) Uani 1 1 d . . . . .
O12 O 0.6312(4) 0.7130(2) 0.9201(4) 0.0634(12) Uani 1 1 d . . . . .
H12 H 0.593567 0.723538 0.847517 0.095 Uiso 1 1 calc R U . . .
P2 P 0.57902(10) 0.67492(7) 0.62893(13) 0.0379(3) Uani 1 1 d . . . . .
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C4 C3 P2 122.1(3) . . ?
C4 C3 H3 119.0 . . ?
P2 C3 H3 119.0 . . ?
C3 C4 C4A 123.0(4) . . ?
C3 C4 C23 118.7(4) . . ?
C4A C4 C23 118.3(4) . . ?
C5 C4A C8A 116.9(4) . . ?
C5 C4A C4 122.4(4) . . ?
C8A C4A C4 120.6(4) . . ?
C6 C5 C4A 121.9(5) . . ?
C6 C5 H5 119.1 . . ?
C4A C5 H5 119.1 . . ?
C5 C6 C7 119.3(5) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C8 C7 C6 120.6(5) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C8A 119.9(5) . . ?
C7 C8 H8 120.1 . . ?
C8A C8 H8 120.1 . . ?
O1 C8A C8 116.4(4) . . ?
O1 C8A C4A 122.2(4) . . ?
C8 C8A C4A 121.4(5) . . ?
C17 C9 C11 111.0(4) . . ?
C17 C9 C10 106.6(3) . . ?
C11 C9 C10 112.2(4) . . ?
C17 C9 P2 114.1(3) . . ?
C11 C9 P2 105.5(3) . . ?
C10 C9 P2 107.4(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 117.0(4) . . ?
C16 C11 C9 120.6(4) . . ?
C12 C11 C9 122.4(4) . . ?
O12 C12 C13 117.2(5) . . ?
O12 C12 C11 123.3(5) . . ?
C13 C12 C11 119.6(5) . . ?
C14 C13 C12 121.9(5) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 119.3(6) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 119.8(5) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C11 122.4(5) . . ?
C15 C16 H16 118.8 . . ?
C11 C16 H16 118.8 . . ?
C22 C17 C18 118.2(4) . . ?
C22 C17 C9 117.7(4) . . ?
C18 C17 C9 123.8(4) . . ?
C17 C18 C19 121.3(5) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C20 C19 C18 118.9(5) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C21 C20 C19 121.3(5) . . ?
C21 C20 Cl20 119.6(4) . . ?
C19 C20 Cl20 119.1(4) . . ?
C20 C21 C22 119.2(5) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C17 C22 C21 121.0(5) . . ?
C17 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C24 C23 C28 118.8(4) . . ?
C24 C23 C4 120.1(4) . . ?
C28 C23 C4 121.0(4) . . ?
C23 C24 C25 120.2(5) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C26 C25 C24 119.5(4) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C25 C26 C27 122.4(4) . . ?
C25 C26 Cl26 119.3(4) . . ?
C27 C26 Cl26 118.3(4) . . ?
C26 C27 C28 117.6(5) . . ?
C26 C27 H27 121.2 . . ?
C28 C27 H27 121.2 . . ?
C23 C28 C27 121.4(4) . . ?
C23 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
C8A O1 P2 126.6(3) . . ?
C12 O12 H12 109.5 . . ?
O2 P2 O1 113.2(2) . . ?
O2 P2 C3 116.2(2) . . ?
O1 P2 C3 103.0(2) . . ?
O2 P2 C9 111.6(2) . . ?
O1 P2 C9 103.5(2) . . ?
C3 P2 C9 108.3(2) . . ?
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
C3 C4 1.350(7) . ?
C3 P2 1.770(4) . ?
C3 H3 0.9500 . ?
C4 C4A 1.468(6) . ?
C4 C23 1.495(6) . ?
C4A C5 1.393(7) . ?
C4A C8A 1.397(6) . ?
C5 C6 1.376(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.389(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.353(8) . ?
C7 H7 0.9500 . ?
C8 C8A 1.390(6) . ?
C8 H8 0.9500 . ?
C8A O1 1.386(6) . ?
C9 C17 1.534(5) . ?
C9 C11 1.538(6) . ?
C9 C10 1.543(6) . ?
C9 P2 1.834(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.397(6) . ?
C11 C12 1.404(6) . ?
C12 O12 1.353(6) . ?
C12 C13 1.396(8) . ?
C13 C14 1.359(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.373(7) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.385(7) . ?
C17 C18 1.386(7) . ?
C18 C19 1.388(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.376(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.368(8) . ?
C20 Cl20 1.743(5) . ?
C21 C22 1.395(6) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.383(6) . ?
C23 C28 1.389(6) . ?
C24 C25 1.387(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.361(7) . ?
C25 H25 0.9500 . ?
C26 C27 1.377(7) . ?
C26 Cl26 1.742(4) . ?
C27 C28 1.390(6) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
O1 P2 1.597(4) . ?
O2 P2 1.475(4) . ?
O12 H12 0.8400 . ?
