Carbon-Carbon Bond Formation by Reaction of Rhodium Azavinylcarbenes with Secondary Amides: Access to Indigo Analogues from Isatins.
Meng, Jiang; Jia, Renmeng; Leng, Jiaying; Wen, Min; Yu, Xingxin; Deng, Wei-Ping; Organic letters 19 (2017) 4520–4523; doi:10.1021/acs.orglett.7b02096

data_1547058
_publ_section_title
;
 Carbon-Carbon Bond Formation by Reaction of Rhodium Azavinylcarbenes with
 Secondary Amides: Access to Indigo Analogues from Isatins.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4520
_journal_page_last               4523
_journal_paper_doi               10.1021/acs.orglett.7b02096
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C24 H18 Cl4 N2 O4 S'
_chemical_formula_weight         572.26
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
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_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
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_cell_angle_beta                 101.576(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   11.6242(12)
_cell_length_c                   18.662(2)
_cell_measurement_reflns_used    2964
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      47.395
_cell_measurement_theta_min      4.869
_cell_volume                     2614.5(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
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_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
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_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14740
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_min         1.690
_exptl_absorpt_coefficient_mu    0.566
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
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_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4872
_refine_ls_number_restraints     44
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0572
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0783P)^2^+1.0793P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1468
_refine_ls_wR_factor_ref         0.1636
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3428
_reflns_number_total             4872
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02096_si_002.cif
_cod_data_source_block           cd16580
_cod_original_cell_volume        2614.4(5)
_cod_database_code               1547058
_shelx_estimated_absorpt_t_min   0.895
_shelx_estimated_absorpt_t_max   0.940
_shelxl_version_number           2013-4
_shelx_res_checksum              90768
_shelx_hkl_checksum              76201