Divergent synthesis of benzoxaphospholenes and phosphacoumarins via the reaction of 2-alkenylphenols with phosphorus(iii/v) chlorides
Tatarinov, Dmitry A.; Mikulenkova, Elina A.; Litvinov, Igor A.; Khayarov, Khasan R.; Mironov, Vladimir F.; Organic & Biomolecular Chemistry 22 (2024) 1629–1633; doi:10.1039/D3OB01718D

data_7159664
_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 &amp; 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         'C14 H10 Cl O3 P'
_chemical_formula_sum            'C14 H10 Cl O3 P'
_chemical_formula_weight         292.64
_chemical_melting_point          426
_chemical_name_systematic
'2-hydroxy-4-methylbenzo[e][1,2]oxaphosphinine 2-oxide '
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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                 91.716(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.5378(3)
_cell_length_b                   10.6153(7)
_cell_length_c                   13.1018(9)
_cell_measurement_reflns_used    9447
_cell_measurement_temperature    164(2)
_cell_measurement_theta_max      34.16
_cell_measurement_theta_min      2.47
_cell_volume                     630.83(7)
_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      164(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            38061
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.996
_diffrn_reflns_theta_min         2.470
_diffrn_source                   'I\mS DIAMOND'
_exptl_absorpt_coefficient_mu    0.429
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.7034
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details
;
 Flack x determined using 2042 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.023(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         4383
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0278
_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/[\s^2^(Fo^2^)+(0.0570P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0712
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4325
_reflns_number_total             4383
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01718d2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7159664--7159669.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7159664
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              89501