Palladium-Catalyzed Coupling of Allenylphosphonates, Phenylallenes, and Allenyl Esters: Remarkable Salt Effect and Routes to Novel Benzofurans and Isocoumarins
Manab Chakravarty; K. C. Kumara Swamy; Journal of Organic Chemistry 71 (2006) 9128–9138; doi:10.1021/jo061525y

data_4022107
_publ_section_title
;
 Palladium-Catalyzed Coupling of Allenylphosphonates, Phenylallenes,
 and Allenyl Esters: Remarkable Salt Effect and Routes to Novel
 Benzofurans and Isocoumarins
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9128
_journal_page_last               9138
_journal_paper_doi               10.1021/jo061525y
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C14 H19 O3 P'
_chemical_formula_weight         266.26
_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                 104.7450(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5521(5)
_cell_length_b                   17.6566(10)
_cell_length_c                   10.9664(7)
_cell_measurement_reflns_used    5397
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.17
_cell_measurement_theta_min      2.24
_cell_volume                     1414.15(15)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      273(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0164
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13364
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.9481
_exptl_absorpt_correction_T_min  0.9218
_exptl_absorpt_correction_type   'empirical sadabs'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2475
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0478
_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^)+(0.0558P)^2^+0.6488P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1228
_reflns_number_gt                2232
_reflns_number_total             2475
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061525ysi20060722_122107_05.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4022107