Visible Light Photocatalytic Asymmetric Synthesis of Pyrrolo[1,2-a]indoles via Intermolecular [3+2] Cycloaddition
Casado-Sanchez, Antonio; Domingo-Legarda, Pablo; Cabrera, Silvia; Aleman, Jose; Chemical Communications  (2019) –; doi:10.1039/C9CC05838A

data_7124064
_publ_section_title
;
 Visible Light Photocatalytic Asymmetric Synthesis of
 Pyrrolo[1,2-a]indoles via Intermolecular [3+2] Cycloaddition
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC05838A
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H23 Br N2 O5'
_chemical_formula_weight         463.32
_chemical_name_common            ACS-953.T9_150K
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2019-07-09 deposited with the CCDC.    2019-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.8079(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.4515(7)
_cell_length_b                   6.59020(10)
_cell_length_c                   16.4904(5)
_cell_measurement_reflns_used    5572
_cell_measurement_temperature    150.(2)
_cell_measurement_theta_max      22.8293
_cell_measurement_theta_min      2.6718
_cell_volume                     2000.89(10)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18040
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.37
_exptl_absorpt_coefficient_mu    2.091
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.256
_refine_ls_abs_structure_details
;

Flack x determined using 1400 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3650
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0266
_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^)+(0.0121P)^2^+3.7850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0496
_refine_ls_wR_factor_ref         0.0622
_reflns_number_gt                3296
_reflns_number_total             3650
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc05838a2.cif
_cod_data_source_block           02721PabloDomingo
_cod_database_code               7124064
_shelx_res_checksum              44857