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_1554944
_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_moiety         'C24 H24 Cl N O'
_chemical_formula_sum            'C24 H24 Cl N O'
_chemical_formula_weight         377.89
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2014-09-10
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874,
 SHELXL-2014,
 and manual edit
;
_cell_angle_alpha                90
_cell_angle_beta                 92.829(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0241(5)
_cell_length_b                   10.8634(4)
_cell_length_c                   15.0306(6)
_cell_measurement_reflns_used    9646
_cell_measurement_temperature    100
_cell_measurement_theta_max      40.72
_cell_measurement_theta_min      2.22
_cell_volume                     1960.94(13)
_computing_cell_refinement       'SAINT V8.34A (Bruker-AXS, 2007)'
_computing_data_collection       'APEX2 2014.5-0 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT V8.34A (Bruker-AXS, 2007)'
_computing_molecular_graphics    'DIAMOND 3 (Crystal Impact, 1999)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'XT-2014/3 (Sheldrick, 2012)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker KAPPA APEX II ccd'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            140172
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         41.861
_diffrn_reflns_theta_min         2.119
_diffrn_source                   'sealed tube'
_diffrn_source_current           30
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0572 before and 0.0537 after correction.
The Ratio of minimum to maximum transmission is 0.9335.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.797
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         13399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0630P)^2^+0.2572P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1120
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10632
_reflns_number_total             13399
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b00743_si_004.cif
_cod_data_source_block           a14340
_cod_database_code               1554944
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.921
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'