Nitrile stabilized synthesis of pyrrolidine and piperidine derivatives <i>via</i> tandem alkynyl aza-Prins-Ritter reactions.
Shit, Sudip; Choudhury, Chinmayee; Saikia, Anil K.; Organic & biomolecular chemistry 22 (2024) 568–578; doi:10.1039/d3ob01764h

data_7159716
_publ_section_title
;
 Nitrile stabilized synthesis of pyrrolidine and piperidine derivatives
 <i>via</i> tandem alkynyl aza-Prins-Ritter reactions.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              568
_journal_page_last               578
_journal_paper_doi               10.1039/d3ob01764h
_journal_volume                  22
_journal_year                    2024
_chemical_formula_sum            'C29 H29 N3 O3 S'
_chemical_formula_weight         499.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-08-07 deposited with the CCDC.	2023-12-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.847(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.290(2)
_cell_length_b                   11.2327(11)
_cell_length_c                   22.560(2)
_cell_measurement_reflns_used    9960
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      22.50
_cell_measurement_theta_min      2.23
_cell_volume                     5345.7(9)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0942
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            123310
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.865
_diffrn_reflns_theta_max         24.865
_diffrn_reflns_theta_min         1.561
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_description       P2(1)/n'
_exptl_crystal_F_000             2112
_refine_diff_density_max         1.384
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.0021(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     662
_refine_ls_number_reflns         9209
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.0701
_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^)+(0.0926P)^2^+5.4443P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1815
_refine_ls_wR_factor_ref         0.2074
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5599
_reflns_number_total             9209
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01764h3.cif
_cod_data_source_block           D_29_D_0m_a
_cod_depositor_comments          'Adding full bibliography for 7159716.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7159716
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              97033