Chelation-Assisted Rhodium-Catalyzed Direct Amidation with Amidobenziodoxolones: C(sp2)–H, C(sp3)–H, and Late-Stage Functionalizations
Hu, Xu-Hong; Yang, Xiao-Fei; Loh, Teck-Peng; ACS Catalysis 6 (2016) 5930–; doi:10.1021/acscatal.6b02015

data_4513933
_publ_section_title
;
 Chelation-Assisted Rhodium-Catalyzed Direct Amidation with
 Amidobenziodoxolones: C(sp2)--H, C(sp3)--H, and Late-Stage
 Functionalizations
;
_journal_issue                   9
_journal_name_full               'ACS Catalysis'
_journal_page_first              5930
_journal_paper_doi               10.1021/acscatal.6b02015
_journal_volume                  6
_journal_year                    2016
_chemical_absolute_configuration abs
_chemical_formula_sum            'C28 H24 Cl3 N3 O7 S'
_chemical_formula_weight         652.91
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                86.937(3)
_cell_angle_beta                 77.911(3)
_cell_angle_gamma                89.004(3)
_cell_formula_units_Z            2
_cell_length_a                   9.8739(10)
_cell_length_b                   10.6233(11)
_cell_length_c                   13.8412(13)
_cell_measurement_reflns_used    2457
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      20.3292
_cell_measurement_theta_min      2.3222
_cell_volume                     1417.6(2)
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XS, VERSION 2013/1'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.1290
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20580
_diffrn_reflns_theta_full        28.40
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         1.51
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'
_exptl_absorpt_coefficient_mu    0.450
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.698
_refine_diff_density_min         -0.814
_refine_ls_abs_structure_details
;

Flack x determined using 2472 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     763
_refine_ls_number_reflns         12775
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1217
_refine_ls_R_factor_gt           0.0710
_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^)+(0.0791P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1508
_refine_ls_wR_factor_ref         0.1851
_reflns_number_gt                8097
_reflns_number_total             12775
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b02015_si_002.cif
_cod_data_source_block           ltp320s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-Scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 4513932--4513933.cif.
;
_cod_database_code               4513933
_shelx_res_checksum              97356
_shelx_hkl_checksum              42894