The Synthesis of Phosphaisocoumarins by Cu(I)-Catalyzed Intramolecular Cyclization of o-Ethynylphenylphosphonic Acid Monoesters
Ai-Yun Peng; Yi-Xiang Ding; Journal of the American Chemical Society 125 (2003) 15006–15007; doi:10.1021/ja038627f

data_4114471
_publ_section_title
;
 The Synthesis of Phosphaisocoumarins by Cu(I)-Catalyzed Intramolecular
 Cyclization of o-Ethynylphenylphosphonic Acid Monoesters
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15006
_journal_page_last               15007
_journal_paper_doi               10.1021/ja038627f
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C17 H17 O4 P'
_chemical_formula_weight         316.28
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.093(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4487(11)
_cell_length_b                   7.6652(8)
_cell_length_c                   19.423(2)
_cell_measurement_reflns_used    2196
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      50.060
_cell_measurement_theta_min      4.860
_cell_volume                     1526.5(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_sigmaI/netI    0.0628
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9000
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61043
_exptl_absorpt_correction_type   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.557
_exptl_crystal_size_mid          0.523
_exptl_crystal_size_min          0.119
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3560
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.894
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0399P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0942
_reflns_number_gt                2373
_reflns_number_total             3560
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja038627fsi20030920_012435.cif
_cod_data_source_block           cd23100
_cod_database_code               4114471