Direct access to benzo[b]fluorenes via a gold-catalysed A3-coupling strategy
Lustosa, Danilo M.; Cieslik, Patrick; Hartmann, Deborah; Bruckhoff, Tim; Rudolph, Matthias; Rominger, Frank; Hashmi, A. Stephen K.; Organic Chemistry Frontiers 6 (2019) 1655–; doi:10.1039/C9QO00260J

data_1554808
_publ_section_title
;
 Direct access to benzo[b]fluorenes via a gold-catalysed A3-coupling
 strategy
;
_journal_issue                   10
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1655
_journal_paper_doi               10.1039/C9QO00260J
_journal_volume                  6
_journal_year                    2019
_chemical_formula_sum            'C27 H23 N O'
_chemical_formula_weight         377.46
_chemical_name_common            '6a in manuscript'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-02-06 deposited with the CCDC.	2019-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.856(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7344(4)
_cell_length_b                   18.9552(12)
_cell_length_c                   15.1244(8)
_cell_measurement_reflns_used    12988
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.62
_cell_measurement_theta_min      3.74
_cell_volume                     1930.4(2)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 0.921
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measurement_device_type  'STOE Stadivari'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 0.921
_diffrn_reflns_Laue_measured_fraction_max 0.868
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7422
_diffrn_reflns_point_group_measured_fraction_full 0.695
_diffrn_reflns_point_group_measured_fraction_max 0.641
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.952
_diffrn_reflns_theta_min         3.739
_diffrn_source                   'Genix3D Cu HF'
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_T_max  1.580
_exptl_absorpt_correction_T_min  0.600
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       'flat needle'
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details
; 
 Flack x determined using 1024 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.578
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         5177
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.578
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0799
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2324
_refine_ls_wR_factor_ref         0.2432
_reflns_Friedel_coverage         0.433
_reflns_Friedel_fraction_full    0.453
_reflns_Friedel_fraction_max     0.400
_reflns_number_gt                4053
_reflns_number_total             5177
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00260j2.cif
_cod_data_source_block           dml3
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1554808
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.926
_shelx_estimated_absorpt_t_max   0.988
_exptl_absorpt_special_details   'STOE X-AREA Laue Analyzer'
_shelx_res_checksum              17618
_shelx_hkl_checksum              29550