Stereospecific assembly of tetrahydroquinolines via tandem ring-opening/oxidative cyclization of donor-acceptor cyclopropanes with N-alkyl anilines
Punniyamurthy, Tharmalingam; Das, Bijay Ketan; Pradhan, Sourav; Chemical Communications  (2019) –; doi:10.1039/C9CC04042K

data_7123646
_publ_section_title
;
 Stereospecific assembly of tetrahydroquinolines via tandem
 ring-opening/oxidative cyclization of donor-acceptor cyclopropanes with
 N-alkyl anilines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC04042K
_journal_year                    2019
_chemical_absolute_configuration s
_chemical_formula_moiety         'C26 H24 Cl N O4'
_chemical_formula_sum            'C26 H24 Cl N O4'
_chemical_formula_weight         449.91
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-03-13 deposited with the CCDC.    2019-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.984(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.5583(10)
_cell_length_b                   9.7573(7)
_cell_length_c                   11.7032(11)
_cell_measurement_reflns_used    1114
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.7960
_cell_measurement_theta_min      3.0830
_cell_volume                     1153.09(19)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.874
_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  0.0649
_diffrn_reflns_av_unetI/netI     0.1023
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4827
_diffrn_reflns_point_group_measured_fraction_full 0.738
_diffrn_reflns_point_group_measured_fraction_max 0.615
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.845
_diffrn_reflns_theta_min         2.288
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76856
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.12(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3728
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0713
_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^)+(0.0718P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1584
_refine_ls_wR_factor_ref         0.1989
_reflns_Friedel_coverage         0.333
_reflns_Friedel_fraction_full    0.441
_reflns_Friedel_fraction_max     0.326
_reflns_number_gt                2194
_reflns_number_total             3728
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc04042k2.cif
_cod_data_source_block           exp_6163
_cod_database_code               7123646
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              83745