Facile Synthesis of 9H-Pyrrolo[1,2-a]indoles Via Brønsted Acid Catalyzed Cascade Reaction
xu, kunhua; chen, wenming; lin, jin; chen, guifang; wang, biao; Xu, Tian; Chemical Communications  (2019) –; doi:10.1039/C9CC07228D

data_7124464
_publ_section_title
;
 Facile Synthesis of 9H-Pyrrolo[1,2-a]indoles Via Br\/onsted Acid
 Catalyzed Cascade Reaction
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC07228D
_journal_year                    2019
_chemical_formula_moiety         'C25 H21 N O'
_chemical_formula_sum            'C25 H21 N O'
_chemical_formula_weight         351.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-31 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   10.580(4)
_cell_length_b                   23.646(9)
_cell_length_c                   30.450(11)
_cell_measurement_reflns_used    6513
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      23.42
_cell_measurement_theta_min      2.21
_cell_volume                     7618(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            44129
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.574
_diffrn_reflns_theta_min         2.645
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.0876 before and 0.0441 after correction. The Ratio of minimum to maximum transmission is 0.8957. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       block
_exptl_crystal_F_000             2976
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.00136(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     492
_refine_ls_number_reflns         8778
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1143
_refine_ls_R_factor_gt           0.0516
_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^)+(0.0501P)^2^+1.9308P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1336
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4958
_reflns_number_total             8778
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07228d2.cif
_cod_data_source_block           190702xt232_0m
_cod_database_code               7124464
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C28(H28)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C34(H34),
  C36(H36), C37(H37), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42),
 C43(H43), C44(H44), C45(H45), C46(H46), C49(H49), C50(H50)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C47(H47A,H47B,H47C), C48(H48A,H48B,
 H48C)
;
_shelx_res_checksum              81006
_olex2_submission_special_instructions 'No special instructions were received'