Synthesis of Fluorenones from Benzaldehydes and Aryl Iodides: Dual C-H Functionalizations Using a Transient Directing Group.
Chen, Xiao-Yang; Ozturk, Seyma; Sorensen, Erik J.; Organic letters 19 (2017) 1140–1143; doi:10.1021/acs.orglett.7b00161

data_1545311
_publ_section_title
;
 Synthesis of Fluorenones from Benzaldehydes and Aryl Iodides: Dual C-H
 Functionalizations Using a Transient Directing Group.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1140
_journal_page_last               1143
_journal_paper_doi               10.1021/acs.orglett.7b00161
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C15 H12 O3'
_chemical_formula_weight         240.25
_chemical_name_common            PDJXC1-44
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 93.5525(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8452(3)
_cell_length_b                   3.9073(2)
_cell_length_c                   36.5490(15)
_cell_measurement_reflns_used    9721
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      68.0748
_cell_measurement_theta_min      4.8492
_cell_volume                     1118.20(8)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'Bruker Instrument Service vV6.2.1'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            11842
_diffrn_reflns_theta_full        66.59
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_min         2.42
_diffrn_source_type              'I\mS microfocus source'
_exptl_absorpt_coefficient_mu    0.811
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            'translucent intense orange'
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.299
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.151
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1988
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0321
_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^)+(0.0363P)^2^+0.5566P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0844
_reflns_number_gt                1844
_reflns_number_total             1988
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00161_si_001.cif
_cod_data_source_block           PDJXC1
_cod_depositor_comments          'Adding full bibliography for 1545311.cif.'
_cod_database_code               1545311
_shelx_res_checksum              73990
_shelx_hkl_checksum              82342