Selective synthesis of pyrrolo[1,2-a]azepines or 4,6-dicarbonyl indoles via tandem reactions of alkynones with pyrrole derivatives
Zhao, Yu-Lei; Yuan, Yang; Xu, Murong; Zheng, Zhong; Zhang, Runhua; LI, Yanzhong; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01516J

data_7155762
_publ_section_title
;
 Selective synthesis of pyrrolo[1,2-a]azepines or 4,6-dicarbonyl indoles
 via tandem reactions of alkynones with pyrrole derivatives
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01516J
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C29 H19 Cl2 N O2'
_chemical_formula_weight         484.35
_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_creation_method           SHELXL-2013
_audit_update_record
;
2017-01-17 deposited with the CCDC.
2017-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.572(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.413(4)
_cell_length_b                   8.3862(13)
_cell_length_c                   12.2342(18)
_cell_measurement_reflns_used    1297
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      39.025
_cell_measurement_theta_min      5.150
_cell_volume                     2444.5(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7073
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_min         1.898
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
; 
 Flack x determined using 995 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.09(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4266
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0555
_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^)+(0.0830P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1364
_refine_ls_wR_factor_ref         0.1542
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.874
_reflns_Friedel_fraction_max     0.871
_reflns_number_gt                2919
_reflns_number_total             4266
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01516j2.cif
_cod_data_source_block           cd16445
_cod_database_code               7155762
_shelx_estimated_absorpt_t_min   0.944
_shelx_estimated_absorpt_t_max   0.966
_shelxl_version_number           2013-4
_shelx_res_checksum
'13328 &#x00EF;&#x00BB;&#x00BF;#######################################################################'