A three-component iodine-catalyzed oxidative coupling reaction: a heterodifunctionalization of 3-methylindoles.
Zhang, Wei; Xiang, Shiqun; Fan, Weibin; Jin, Jiang; Li, Yinghua; Huang, Deguang; Organic & biomolecular chemistry 19 (2021) 5794–5799; doi:10.1039/d1ob00730k

data_7158113
_publ_section_title
;
 A three-component iodine-catalyzed oxidative coupling reaction: a
 heterodifunctionalization of 3-methylindoles.
;
_journal_issue                   26
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5794
_journal_page_last               5799
_journal_paper_doi               10.1039/d1ob00730k
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C19 H24 N2 O4'
_chemical_formula_sum            'C19 H24 N2 O4'
_chemical_formula_weight         344.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-03-04 deposited with the CCDC.	2021-06-01 downloaded from the CCDC.
;
_cell_angle_alpha                101.921(6)
_cell_angle_beta                 111.131(7)
_cell_angle_gamma                105.454(5)
_cell_formula_units_Z            2
_cell_length_a                   9.9866(6)
_cell_length_b                   10.4170(6)
_cell_length_c                   10.4938(8)
_cell_measurement_reflns_used    3066
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.5240
_cell_measurement_theta_min      4.6390
_cell_volume                     924.18(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.5594
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7446
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.916
_diffrn_reflns_theta_min         4.677
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3569
_refine_ls_number_restraints     221
_refine_ls_restrained_S_all      1.204
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0622
_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^)+(0.0805P)^2^+1.0122P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1606
_refine_ls_wR_factor_ref         0.1732
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2924
_reflns_number_total             3569
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00730k2.cif
_cod_data_source_block           Compound3o
_cod_depositor_comments
'Adding full bibliography for 7158113--7158115.cif.'
_cod_original_cell_volume        924.17(12)
_cod_database_code               7158113
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.815
_shelx_estimated_absorpt_t_max   0.901
_shelx_res_checksum              3519
_shelx_hkl_checksum              92345