Dual Role of Acetanilides: Traceless Removal of a Directing Group through Deacetylation/Diazotation and Palladium-Catalyzed C-C-Coupling Reactions.
Schmidt, Bernd; Elizarov, Nelli; Schilde, Uwe; Kelling, Alexandra; The Journal of organic chemistry 80 (2015) 4223–4234; doi:10.1021/acs.joc.5b00272

data_4036151
_publ_section_title
;
 Dual Role of Acetanilides: Traceless Removal of a Directing Group through
 Deacetylation/Diazotation and Palladium-Catalyzed C-C-Coupling Reactions.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4223
_journal_page_last               4234
_journal_paper_doi               10.1021/acs.joc.5b00272
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C16 H12 N2 O'
_chemical_formula_sum            'C16 H12 N2 O'
_chemical_formula_weight         248.28
_chemical_melting_point          488
_chemical_name_systematic
;
 8-Phenyl-3a,8-dihydro-3H-pyrazolo[5,1-a]isoindol-2-ol
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 109.568(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7196(7)
_cell_length_b                   5.8118(2)
_cell_length_c                   15.2737(6)
_cell_measurement_reflns_used    12642
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      29.10
_cell_measurement_theta_min      1.66
_cell_volume                     1231.16(9)
_computing_cell_refinement       'X-AREA (Stoe, 2004)'
_computing_data_collection       'X-AREA (Stoe, 2004)'
_computing_data_reduction        'X-RED (Stoe, 2004)'
_computing_molecular_graphics
;
 DIAMOND (Brandenburg, 2014)
 ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_structure_refinement  'SHELXL-2013/2 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_diffrn_ambient_temperature      210(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
 360 frames, exposure time per frame = 5 min
;
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       '\w scan, 1.0 \%'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15108
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         1.663
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_correction_T_min  0.9710
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'X-RED (Stoe, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0159(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0332
_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^)+(0.0536P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0822
_reflns_number_gt                1588
_reflns_number_total             2169
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00272_si_002.cif
_cod_data_source_block           n1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4036151