A Copper-Catalyzed Tandem Reaction for the Construction of Coumarin Fused 9H-Pyrrolo[1,2-a]indoles
Jin, Shao-Jing; Guo, Jiao-Mei; Zhu, Yan-Shuo; Wang, Qi-Lin; Bu, Zhanwei; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB02307C

data_7155904
_publ_section_title
;
 A Copper-Catalyzed Tandem Reaction for the Construction of Coumarin Fused
 9H-Pyrrolo[1,2-a]indoles
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB02307C
_journal_year                    2017
_chemical_formula_moiety         'C25 H16 F N O2'
_chemical_formula_sum            'C25 H16 F N O2'
_chemical_formula_weight         381.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-07-25 deposited with the CCDC.
2017-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.219(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.9398(17)
_cell_length_b                   10.9448(10)
_cell_length_c                   16.3541(14)
_cell_measurement_reflns_used    5512
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.86
_cell_measurement_theta_min      2.42
_cell_volume                     3554.3(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19608
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.131
_diffrn_reflns_theta_min         2.051
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.320
_exptl_transmission_factor_max   0.4939
_exptl_transmission_factor_min   0.4368
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         5309
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0535
_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^)+(0.0545P)^2^+6.6731P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1380
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4120
_reflns_number_total             5309
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02307c2.cif
_cod_data_source_block           mo_hd_wql19_0m
_cod_database_code               7155904
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.957
_shelx_estimated_absorpt_t_max   0.969
_shelx_res_checksum              35035