Regio- and Diastereoselective Indium-Catalyzed Conia-Ene Reaction of <i>ortho</i>-Alkynyl Diketopiperazines to Access Fused Diketopiperazinoindolines.
Tejeneki, Hossein Zahedian; Nikbakht, Ali; Balalaie, Saeed; Rominger, Frank; The Journal of organic chemistry 85 (2020) 8544–8552; doi:10.1021/acs.joc.0c00895

data_4038520
_publ_section_title
;
 Regio- and Diastereoselective Indium-Catalyzed Conia-Ene Reaction of
 <i>ortho</i>-Alkynyl Diketopiperazines to Access Fused
 Diketopiperazinoindolines.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8544
_journal_page_last               8552
_journal_paper_doi               10.1021/acs.joc.0c00895
_journal_volume                  85
_journal_year                    2020
_chemical_formula_sum            'C31 H27 Br N2 O2'
_chemical_formula_weight         539.45
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5188(10)
_cell_length_b                   21.4989(13)
_cell_length_c                   7.5658(5)
_cell_measurement_reflns_used    5723
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      66.25
_cell_measurement_theta_min      3.51
_cell_volume                     2524.2(3)
_computing_cell_refinement       'X-Area Recipe 1.33.0.0 (STOE, 2015)'
_computing_data_collection       'X-Area Pilatus3_SV 1.31.144.0 (STOE, 2018)'
_computing_data_reduction        'X-Area Integrate 1.73.0.0 (STOE, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'STOE Stadivari'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0999
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            8845
_diffrn_reflns_point_group_measured_fraction_full 0.891
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_theta_full        67.035
_diffrn_reflns_theta_max         67.035
_diffrn_reflns_theta_min         3.512
_diffrn_source                   'Genix3D Cu HF'
_exptl_absorpt_coefficient_mu    2.465
_exptl_absorpt_correction_T_max  1.621
_exptl_absorpt_correction_T_min  0.708
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       needle
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.162
_exptl_crystal_size_mid          0.044
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
; 
 Flack x determined using 624 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.46(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     578
_refine_ls_number_reflns         4003
_refine_ls_number_restraints     1962
_refine_ls_restrained_S_all      0.812
_refine_ls_R_factor_all          0.1195
_refine_ls_R_factor_gt           0.0583
_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^)+(0.0720P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1477
_reflns_Friedel_coverage         0.595
_reflns_Friedel_fraction_full    0.780
_reflns_Friedel_fraction_max     0.779
_reflns_number_gt                2340
_reflns_number_total             4003
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00895_si_002.cif
_cod_data_source_block           sba164
_cod_depositor_comments
'Adding full bibliography for 4038519--4038520.cif.'
_cod_database_code               4038520
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.691
_shelx_estimated_absorpt_t_max   0.934
_exptl_absorpt_special_details   'X-Area LANA 1.70.0.0 (STOE, 2017)'
_shelx_res_checksum              22001
_shelx_hkl_checksum              91421