Access to Fused Pyrroles from Cyclic 1,3-Dienyl Boronic Esters and Arylnitroso Compounds.
François, Benjamin; Eberlin, Ludovic; Berrée, Fabienne; Whiting, Andrew; Carboni, Bertrand; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03214

data_4038173
_publ_section_title
;
 Access to Fused Pyrroles from Cyclic 1,3-Dienyl Boronic Esters and
 Arylnitroso Compounds.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03214
_journal_year                    2020
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H20 N2 O2 S'
_chemical_formula_sum            'C20 H20 N2 O2 S'
_chemical_formula_weight         352.44
_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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 103.123(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.986(4)
_cell_length_b                   9.394(3)
_cell_length_c                   17.213(7)
_cell_measurement_reflns_used    829
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.3497
_cell_measurement_theta_min      2.9586
_cell_measurement_wavelength     0.710730
_cell_volume                     1730.0(11)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
'PLATON, A.L.Spek, Acta Cryst. 2009, D65, 148-155'
_computing_publication_material
'CRYSCALC (T. Roisnel, local program, ver. 2020)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (G. Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      0.0754486
_diffrn_orient_matrix_UB_12      -0.0244227
_diffrn_orient_matrix_UB_13      0.0425289
_diffrn_orient_matrix_UB_21      0.0498557
_diffrn_orient_matrix_UB_22      -0.0118247
_diffrn_orient_matrix_UB_23      -0.0414924
_diffrn_orient_matrix_UB_31      0.0236276
_diffrn_orient_matrix_UB_32      0.1029386
_diffrn_orient_matrix_UB_33      0.0053239
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1128
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            24935
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.596
_diffrn_reflns_theta_min         2.430
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0486
_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^)+(0.0544P)^2^+1.0504P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2808
_reflns_number_total             3974
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b03214_si_003.cif
_cod_data_source_block           BF3_129x2
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4038173
_shelx_res_checksum              68884
_shelx_hkl_checksum              77239