Alkenylation of phosphacoumarins via aerobic oxidative Heck reactions and their synthetic application to fluorescent benzophosphacoumarins.
Kim, Cheol-Eui; Son, Jeong-Yu; Shin, Seohyun; Seo, Boram; Lee, Phil Ho; Organic letters 17 (2015) 908–911; doi:10.1021/acs.orglett.5b00020

data_1554755
_publ_section_title
;
 Alkenylation of phosphacoumarins via aerobic oxidative Heck reactions and
 their synthetic application to fluorescent benzophosphacoumarins.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              908
_journal_page_last               911
_journal_paper_doi               10.1021/acs.orglett.5b00020
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C22 H25 O5 P'
_chemical_formula_weight         400.39
_chemical_name_common            KCE2
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                89.1605(15)
_cell_angle_beta                 82.9814(16)
_cell_angle_gamma                69.4905(14)
_cell_formula_units_Z            2
_cell_length_a                   7.8931(2)
_cell_length_b                   9.4542(2)
_cell_length_c                   14.3399(4)
_cell_measurement_reflns_used    7415
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      25.1080
_cell_measurement_theta_min      2.3011
_cell_volume                     994.29(4)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25892
_diffrn_reflns_theta_full        28.56
_diffrn_reflns_theta_max         28.56
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.337
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         5054
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0635
_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^)+(0.1045P)^2^+0.1514P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1755
_refine_ls_wR_factor_ref         0.2068
_reflns_number_gt                2940
_reflns_number_total             5054
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b00020_si_001.cif
_cod_data_source_block           I
_cod_database_code               1554755