Regio- and Stereoselective Pd-Catalyzed Direct Arylation of Unactivated sp(3) C(3)-H Bonds of Tetrahydrofuran and 1,4-Benzodioxane Systems.
Parella, Ramarao; Babu, Srinivasarao Arulananda; The Journal of organic chemistry 80 (2015) 2339–2355; doi:10.1021/acs.joc.5b00025

data_4030752
_publ_section_title
;
 Regio- and Stereoselective Pd-Catalyzed Direct Arylation of Unactivated
 sp(3) C(3)-H Bonds of Tetrahydrofuran and 1,4-Benzodioxane Systems.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2339
_journal_page_last               2355
_journal_paper_doi               10.1021/acs.joc.5b00025
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C22 H16 N2 O3 S'
_chemical_formula_sum            'C22 H16 N2 O3 S'
_chemical_formula_weight         388.43
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-10-01T20:34:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
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_cell_angle_beta                 99.083(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_c                   16.808(3)
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_cell_measurement_temperature    298
_cell_measurement_theta_max      24.56
_cell_measurement_theta_min      2.45
_cell_volume                     1833.4(5)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
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_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
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_diffrn_reflns_limit_k_min       -10
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_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21545
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         1.828
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0679 before and 0.0582 after correction.
        The Ratio of minimum to maximum transmission is 0.9222.
        The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
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_exptl_crystal_size_mid          0.2
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_refine_ls_extinction_coef       0.008(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3353
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0813
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1814P)^2^+1.5432P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2587
_refine_ls_wR_factor_ref         0.2827
_reflns_number_gt                2546
_reflns_number_total             3353
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00025_si_004.cif
_cod_data_source_block           sci225_pr2036b2_0m
_cod_original_cell_volume        1833.5(5)
_cod_database_code               4030752