Synthesis of substituted dihydrobenzofurans via tandem S(N)Ar/5-exo-trig cyclization.
Koy, Maximilian; Engle, Keary M.; Henling, Lawrence M.; Takase, Michael K.; Grubbs, Robert H.; Organic letters 17 (2015) 1986–1989; doi:10.1021/acs.orglett.5b00743

data_1554941
_publ_section_title
;
 Synthesis of substituted dihydrobenzofurans via tandem S(N)Ar/5-exo-trig
 cyclization.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1986
_journal_page_last               1989
_journal_paper_doi               10.1021/acs.orglett.5b00743
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C39 H30 Cl N O'
_chemical_formula_weight         564.09
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 110.0396(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7817(5)
_cell_length_b                   10.4931(3)
_cell_length_c                   20.1054(7)
_cell_measurement_reflns_used    9423
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      34.19
_cell_measurement_theta_min      2.43
_cell_volume                     2929.66(17)
_computing_cell_refinement       'SAINT v8.34A (Bruker-AXS, 2007)'
_computing_data_collection       'APEX2 v2014.7-1 (Bruker-AXS, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker-AXS, 2007)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_diffrn_ambient_temperature      160(2)
_diffrn_detector_area_resol_mean 10.24
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            118977
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.503
_diffrn_reflns_theta_min         2.449
_diffrn_source                   'I\mS HB micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.7196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/3 (Sheldrick, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.694
_refine_diff_density_min         -0.577
_refine_diff_density_rms         0.176
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         8923
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0745P)^2^+1.3587P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1495
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7125
_reflns_number_total             8923
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b00743_si_003.cif
_cod_data_source_block           P14056
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1554941
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.968
_shelxl_version_number           2014/6
_shelx_res_checksum              21796
_shelx_hkl_checksum              31805