How To Achieve High Regioselectivity in Barrier-less Nucleophilic Addition to p-Benzynes Generated via Bergman Cyclization of Unsymmetrical Cyclic Azaenediyne?
Das, Eshani; Basak, Shyam; Anoop, Anakuthil; Chand, Santanu; Basak, Amit; The Journal of organic chemistry 84 (2019) 2911–2921; doi:10.1021/acs.joc.9b00060

data_4033692
_publ_section_title
;
 How To Achieve High Regioselectivity in Barrier-less Nucleophilic
 Addition to p-Benzynes Generated via Bergman Cyclization of Unsymmetrical
 Cyclic Azaenediyne?
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2911
_journal_page_last               2921
_journal_paper_doi               10.1021/acs.joc.9b00060
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C21 H19 N O3 S'
_chemical_formula_weight         365.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90.00
_cell_angle_beta                 94.59(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.580(2)
_cell_length_b                   6.697(2)
_cell_length_c                   14.995(3)
_cell_measurement_reflns_used    2772
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.574
_cell_measurement_theta_min      2.348
_cell_volume                     858.9(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  empirical
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11098
_diffrn_reflns_point_group_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.445
_diffrn_reflns_theta_min         2.381
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       needle
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 949 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3232
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0450P)^2^+0.1923P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0993
_reflns_Friedel_coverage         0.682
_reflns_Friedel_fraction_full    0.846
_reflns_Friedel_fraction_max     0.810
_reflns_number_gt                2772
_reflns_number_total             3232
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00060_si_003.cif
_cod_data_source_block           ab_ed_177
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4033692
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              38236
_shelx_hkl_checksum              90972