Experimental and computational studies on H<sub>2</sub>O-promoted, Rh-catalyzed transient-ligand-free ortho-C(sp<sup>2</sup>)-H amidation of benzaldehydes with dioxazolones.
Ding, Jun; Jiang, Wei; Bai, He-Yuan; Ding, Tong-Mei; Gao, Dafang; Bao, Xiaoguang; Zhang, Shu-Yu; Chemical communications (Cambridge, England) 54 (2018) 8889–8892; doi:10.1039/c8cc04904a

data_7121994
_publ_section_title
;
 Experimental and computational studies on H<sub>2</sub>O-promoted,
 Rh-catalyzed transient-ligand-free ortho-C(sp<sup>2</sup>)-H amidation of
 benzaldehydes with dioxazolones.
;
_journal_issue                   64
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8889
_journal_page_last               8892
_journal_paper_doi               10.1039/c8cc04904a
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H10 Br N O2'
_chemical_formula_sum            'C14 H10 Br N O2'
_chemical_formula_weight         304.13
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-01-26 deposited with the CCDC.
2018-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   13.3741(4)
_cell_length_c                   26.3417(7)
_cell_measurement_reflns_used    5072
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.56
_cell_measurement_theta_min      3.36
_cell_volume                     1366.45(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            6591
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        66.568
_diffrn_reflns_theta_max         66.568
_diffrn_reflns_theta_min         3.355
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    4.053
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_description       block
_exptl_crystal_F_000             1258
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         2.609
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.237
_refine_ls_abs_structure_details
;
 Flack x determined using 841 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2395
_refine_ls_number_restraints     44
_refine_ls_restrained_S_all      1.170
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0613
_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^)+(0.1375P)^2^+2.0362P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2012
_refine_ls_wR_factor_ref         0.2048
_reflns_Friedel_coverage         0.627
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                2255
_reflns_number_total             2395
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc04904a2.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 7121994--7121995.cif.'
_cod_database_code               7121994
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              505