Metal-Free and Regioselective Synthesis of Substituted and Fused Chromenopyrrole Scaffolds via Divergent Reactivity of α-Azido Ketone in Water.
Dhanasekar, Elumalai; Kannan, Tharanikkarasu; Venkatesan, Ragavan; Perumal, Paramasivam Thirumalai; Kamalraja, Jayabal; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00978

data_4038598
_publ_section_title
;
 Metal-Free and Regioselective Synthesis of Substituted and Fused
 Chromenopyrrole Scaffolds via Divergent Reactivity of \a-Azido Ketone in
 Water.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00978
_journal_year                    2020
_chemical_formula_moiety         'C34 H29 Br2 N3 O5 S2'
_chemical_formula_sum            'C34 H29 Br2 N3 O5 S2'
_chemical_formula_weight         783.54
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                70.9079(14)
_cell_angle_beta                 72.8568(15)
_cell_angle_gamma                81.4490(16)
_cell_formula_units_Z            2
_cell_length_a                   11.6878(4)
_cell_length_b                   12.5438(4)
_cell_length_c                   13.3312(4)
_cell_measurement_reflns_used    4773
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.25
_cell_measurement_theta_min      2.44
_cell_volume                     1761.95(10)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0424
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25573
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.721
_exptl_absorpt_coefficient_mu    2.463
_exptl_absorpt_correction_T_max  0.666
_exptl_absorpt_correction_T_min  0.578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_description       Block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.807
_refine_diff_density_min         -0.829
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         6171
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0531
_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^)+(0.0621P)^2^+1.9178P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1477
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3824
_reflns_number_total             6171
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00978_si_002.cif
_cod_data_source_block           101j
_cod_database_code               4038598
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.578
_shelx_estimated_absorpt_t_max   0.666
_shelx_res_checksum              80515
_shelx_hkl_checksum              75215