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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/7/15/96/7159667.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_7159667
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         'C30 H27 O3 P'
_chemical_formula_sum            'C30 H27 O3 P'
_chemical_formula_weight         466.48
_chemical_melting_point          492
_chemical_name_systematic
'2-(1-(2-hydroxyphenyl)-1-(p-tolyl)ethyl)-4-(p-tolyl)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   mixed
_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                 107.119(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.552(6)
_cell_length_b                   18.511(4)
_cell_length_c                   11.652(3)
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    135(2)
_cell_measurement_theta_max      32.39
_cell_measurement_theta_min      2.45
_cell_volume                     2381.3(15)
_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      135(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.985
_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  0.1026
_diffrn_reflns_av_unetI/netI     0.0792
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            77457
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.000
_diffrn_reflns_theta_min         2.134
_diffrn_source                   'I\mS DIAMOND'
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.7302
_exptl_absorpt_correction_T_min  0.6824
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       formless
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         8158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.1151
_refine_ls_R_factor_gt           0.0574
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0430P)²+1.7996P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1483
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5495
_reflns_number_total             8158
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01718d2.cif
_cod_data_source_block           shelx_CCDC3
_cod_depositor_comments
'Adding full bibliography for 7159664--7159669.cif.'
_cod_original_cell_volume        2381.2(14)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7159667
_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 0.70212(16) 0.35099(11) 0.58511(16) 0.0280(4) Uani 1 1 d . . . . .
H3 H 0.775169 0.359123 0.644016 0.034 Uiso 1 1 calc R U . . .
C4 C 0.69739(16) 0.36114(10) 0.46840(16) 0.0254(3) Uani 1 1 d . . . . .
C4A C 0.58543(16) 0.34807(10) 0.36933(16) 0.0258(3) Uani 1 1 d . . . . .
C5 C 0.58444(18) 0.34876(11) 0.24885(17) 0.0317(4) Uani 1 1 d . . . . .
H5 H 0.655956 0.358332 0.230387 0.038 Uiso 1 1 calc R U . . .
C6 C 0.4794(2) 0.33551(12) 0.15646(18) 0.0388(5) Uani 1 1 d . . . . .
H6 H 0.480661 0.336880 0.077044 0.047 Uiso 1 1 calc R U . . .
C7 C 0.3724(2) 0.32018(12) 0.18286(19) 0.0394(5) Uani 1 1 d . . . . .
H7 H 0.301816 0.311390 0.120959 0.047 Uiso 1 1 calc R U . . .
C8 C 0.37028(18) 0.31794(12) 0.30079(18) 0.0347(4) Uani 1 1 d . . . . .
H8 H 0.298808 0.307401 0.318710 0.042 Uiso 1 1 calc R U . . .
C8A C 0.47625(17) 0.33163(11) 0.39225(16) 0.0285(4) Uani 1 1 d . . . . .
C9 C 0.54308(15) 0.39437(10) 0.72495(15) 0.0229(3) Uani 1 1 d . . . . .
C10 C 0.51766(17) 0.46460(11) 0.64978(17) 0.0305(4) Uani 1 1 d . . . . .
H10A H 0.442509 0.459902 0.587072 0.046 Uiso 1 1 calc R U . . .
H10B H 0.582153 0.472965 0.614962 0.046 Uiso 1 1 calc R U . . .
H10C H 0.512531 0.504520 0.700651 0.046 Uiso 1 1 calc R U . . .
C11 C 0.65815(15) 0.40027(10) 0.83349(15) 0.0238(3) Uani 1 1 d . . . . .
C12 C 0.69086(18) 0.34657(11) 0.92295(17) 0.0315(4) Uani 1 1 d . . . . .
C13 C 0.7937(2) 0.35577(14) 1.02131(19) 0.0424(5) Uani 1 1 d . . . . .
H13 H 0.812518 0.321028 1.081634 0.051 Uiso 1 1 calc R U . . .
C14 C 0.86730(19) 0.41469(15) 1.03087(19) 0.0435(5) Uani 1 1 d . . . . .
H14 H 0.935837 0.419562 1.096628 0.052 Uiso 1 1 calc R U . . .
C15 C 0.83934(18) 0.46688(13) 0.94246(18) 0.0372(5) Uani 1 1 d . . . . .
H15 H 0.889693 0.506701 0.947543 0.045 Uiso 1 1 calc R U . . .
C16 C 0.73523(17) 0.45958(11) 0.84553(16) 0.0283(4) Uani 1 1 d . . . . .
H16 H 0.716542 0.495397 0.786986 0.034 Uiso 1 1 calc R U . . .
C17 C 0.43006(16) 0.37910(10) 0.76557(16) 0.0253(3) Uani 1 1 d . . . . .
C18 C 0.3412(2) 0.32975(12) 0.7095(2) 0.0405(5) Uani 1 1 d . . . . .
H18 H 0.351673 0.301230 0.647646 0.049 Uiso 1 1 calc R U . . .
C19 C 0.2361(2) 0.32214(13) 0.7444(2) 0.0416(5) Uani 1 1 d . . . . .
H19 H 0.178487 0.288019 0.706386 0.050 Uiso 1 1 calc R U . . .
C20 C 0.21627(17) 0.36443(11) 0.83449(19) 0.0333(4) Uani 1 1 d . . . . .
C21 C 0.30429(18) 0.41475(13) 0.88943(18) 0.0355(4) Uani 1 1 d . . . . .
H21 H 0.292599 0.444126 0.949814 0.043 Uiso 1 1 calc R U . . .
C22 C 0.40970(17) 0.42199(12) 0.85570(16) 0.0307(4) Uani 1 1 d . . . . .
H22 H 0.467383 0.456013 0.894001 0.037 Uiso 1 1 calc R U . . .
C23 C 0.1008(2) 0.35667(14) 0.8700(2) 0.0450(6) Uani 1 1 d . . . . .
H23A H 0.120370 0.341987 0.952542 0.067 Uiso 1 1 calc R U . . .
H23B H 0.049699 0.320943 0.820111 0.067 Uiso 1 1 calc R U . . .
H23C H 0.059080 0.402164 0.859891 0.067 Uiso 1 1 calc R U . . .
C24 C 0.80842(16) 0.38463(10) 0.43870(15) 0.0255(3) Uani 1 1 d . . . . .
C25 C 0.91561(17) 0.34587(11) 0.48175(18) 0.0309(4) Uani 1 1 d . . . . .
H25 H 0.917501 0.304962 0.528597 0.037 Uiso 1 1 calc R U . . .
C26 C 1.01982(17) 0.36782(11) 0.45530(18) 0.0327(4) Uani 1 1 d . . . . .
H26 H 1.090521 0.340924 0.483577 0.039 Uiso 1 1 calc R U . . .
C27 C 1.01995(17) 0.42912(11) 0.38748(17) 0.0308(4) Uani 1 1 d . . . . .
C28 C 0.91342(18) 0.46841(11) 0.34657(17) 0.0323(4) Uani 1 1 d . . . . .
H28 H 0.912328 0.510122 0.301772 0.039 Uiso 1 1 calc R U . . .
C29 C 0.80868(18) 0.44647(11) 0.37140(17) 0.0307(4) Uani 1 1 d . . . . .
H29 H 0.738032 0.473367 0.342787 0.037 Uiso 1 1 calc R U . . .
C30 C 1.1330(2) 0.45127(14) 0.3569(2) 0.0426(5) Uani 1 1 d . . . . .
H30A H 1.140685 0.422925 0.290558 0.064 Uiso 1 1 calc R U . . .
H30B H 1.202408 0.443497 0.425249 0.064 Uiso 1 1 calc R U . . .
H30C H 1.127875 0.501502 0.335507 0.064 Uiso 1 1 calc R U . . .
O1 O 0.46672(12) 0.32869(9) 0.50786(12) 0.0384(4) Uani 1 1 d . . . . .
O2 O 0.58613(13) 0.25119(8) 0.68751(14) 0.0380(3) Uani 1 1 d . . . . .
O12 O 0.62463(15) 0.28562(9) 0.92152(16) 0.0423(4) Uani 1 1 d . . . . .
P2 P 0.57626(4) 0.32311(3) 0.63011(4) 0.02811(12) Uani 1 1 d . . . . .
H12 H 0.594(3) 0.2701(17) 0.844(3) 0.068(10) Uiso 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'
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 123.04(14) . . ?
C4 C3 H3 118.5 . . ?
P2 C3 H3 118.5 . . ?
C3 C4 C4A 121.83(16) . . ?
C3 C4 C24 119.34(16) . . ?
C4A C4 C24 118.82(15) . . ?
C8A C4A C5 116.87(17) . . ?
C8A C4A C4 121.19(16) . . ?
C5 C4A C4 121.89(16) . . ?
C6 C5 C4A 121.59(19) . . ?
C6 C5 H5 119.2 . . ?
C4A C5 H5 119.2 . . ?
C5 C6 C7 119.79(19) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 120.25(19) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C8A 119.20(19) . . ?
C7 C8 H8 120.4 . . ?
C8A C8 H8 120.4 . . ?
O1 C8A C8 115.77(17) . . ?
O1 C8A C4A 121.95(16) . . ?
C8 C8A C4A 122.28(18) . . ?
C17 C9 C11 111.36(14) . . ?
C17 C9 C10 106.95(14) . . ?
C11 C9 C10 112.23(15) . . ?
C17 C9 P2 113.57(12) . . ?
C11 C9 P2 105.20(12) . . ?
C10 C9 P2 107.59(12) . . ?
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 117.18(17) . . ?
C16 C11 C9 120.52(16) . . ?
C12 C11 C9 122.29(16) . . ?
O12 C12 C13 116.77(19) . . ?
O12 C12 C11 123.27(18) . . ?
C13 C12 C11 119.93(19) . . ?
C14 C13 C12 121.5(2) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 119.6(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 119.6(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C11 122.09(19) . . ?
C15 C16 H16 119.0 . . ?
C11 C16 H16 119.0 . . ?
C18 C17 C22 117.75(17) . . ?
C18 C17 C9 123.63(16) . . ?
C22 C17 C9 118.32(16) . . ?
C17 C18 C19 121.1(2) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 121.1(2) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C20 C21 117.88(17) . . ?
C19 C20 C23 120.7(2) . . ?
C21 C20 C23 121.45(19) . . ?
C20 C21 C22 121.15(19) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C17 C22 C21 120.99(19) . . ?
C17 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C29 C24 C25 118.66(17) . . ?
C29 C24 C4 121.17(17) . . ?
C25 C24 C4 120.14(17) . . ?
C26 C25 C24 120.47(18) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C27 C26 C25 120.91(18) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C26 C27 C28 118.45(17) . . ?
C26 C27 C30 120.31(19) . . ?
C28 C27 C30 121.23(19) . . ?
C29 C28 C27 121.03(19) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C28 C29 C24 120.47(18) . . ?
C28 C29 H29 119.8 . . ?
C24 C29 H29 119.8 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C8A O1 P2 126.72(12) . . ?
C12 O12 H12 109(2) . . ?
O2 P2 O1 113.24(9) . . ?
O2 P2 C3 115.96(9) . . ?
O1 P2 C3 102.77(9) . . ?
O2 P2 C9 112.16(8) . . ?
O1 P2 C9 103.80(8) . . ?
C3 P2 C9 107.82(9) . . ?
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 1.358(2) . ?
C3 P2 1.7616(19) . ?
C3 H3 0.9300 . ?
C4 C4A 1.478(3) . ?
C4 C24 1.488(2) . ?
C4A C8A 1.397(3) . ?
C4A C5 1.401(2) . ?
C5 C6 1.386(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.389(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.382(3) . ?
C7 H7 0.9300 . ?
C8 C8A 1.389(3) . ?
C8 H8 0.9300 . ?
C8A O1 1.384(2) . ?
C9 C17 1.540(2) . ?
C9 C11 1.545(3) . ?
C9 C10 1.547(3) . ?
C9 P2 1.8325(18) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C16 1.394(3) . ?
C11 C12 1.409(3) . ?
C12 O12 1.361(3) . ?
C12 C13 1.397(3) . ?
C13 C14 1.367(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.393(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.386(3) . ?
C17 C22 1.391(3) . ?
C18 C19 1.396(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.381(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.388(3) . ?
C20 C23 1.516(3) . ?
C21 C22 1.392(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C29 1.388(3) . ?
C24 C25 1.391(3) . ?
C25 C26 1.388(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.383(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.388(3) . ?
C27 C30 1.508(3) . ?
C28 C29 1.385(3) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
O1 P2 1.6061(16) . ?
O2 P2 1.4792(16) . ?
O12 H12 0.91(3) . ?
