Phosphine-Mediated Iterative Arene Homologation Using Allenes.
Zhang, Kui; Cai, Lingchao; Jiang, Xing; Garcia-Garibay, Miguel A; Kwon, Ohyun; Journal of the American Chemical Society 137 (2015) 11258–11261; doi:10.1021/jacs.5b07403

data_4124608
_publ_section_title
;
 Phosphine-Mediated Iterative Arene Homologation Using Allenes.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11258
_journal_page_last               11261
_journal_paper_doi               10.1021/jacs.5b07403
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C20 H17 N O5'
_chemical_formula_sum            'C20 H17 N O5'
_chemical_formula_weight         351.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 100.248(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   5.4689(2)
_cell_length_c                   24.7977(9)
_cell_measurement_reflns_used    4843
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.12
_cell_measurement_theta_min      3.62
_cell_volume                     1612.41(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
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_computing_publication_material  'Bruker SHELXTL'
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_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
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_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            15302
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.199
_diffrn_reflns_theta_min         3.622
_diffrn_source                   'I\mS micro--focus source'
_exptl_absorpt_coefficient_mu    0.869
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.54
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3122
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0640P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1028
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2558
_reflns_number_total             3122
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b07403_si_002.cif
_cod_data_source_block           cu_kw1404s_a
_cod_database_code               4124608
_shelxl_version_number           2014-3
_shelx_res_checksum              92385
_shelx_hkl_checksum              76370