Synthesis of Tetrahydropyridine Derivatives through a Reaction of 1,6-Enynes, Sulfur Dioxide, and Aryldiazonium Tetrafluoroborates.
An, Yuanyuan; Wu, Jie; Organic letters 19 (2017) 6028–6031; doi:10.1021/acs.orglett.7b03195

data_1547783
_publ_section_title
;
 Synthesis of Tetrahydropyridine Derivatives through a Reaction of
 1,6-Enynes, Sulfur Dioxide, and Aryldiazonium Tetrafluoroborates.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              6028
_journal_page_last               6031
_journal_paper_doi               10.1021/acs.orglett.7b03195
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C27 H29 N3 O4 S2'
_chemical_formula_weight         523.65
_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
_cell_angle_alpha                90
_cell_angle_beta                 95.755(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.9678(18)
_cell_length_b                   10.943(3)
_cell_length_c                   15.044(4)
_cell_measurement_reflns_used    1336
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      21.28
_cell_measurement_theta_min      2.31
_cell_volume                     1305.1(6)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.986
_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  0.0517
_diffrn_reflns_av_unetI/netI     0.0910
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8419
_diffrn_reflns_point_group_measured_fraction_full 0.755
_diffrn_reflns_point_group_measured_fraction_max 0.741
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.406
_diffrn_reflns_theta_min         2.305
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
; 
 Flack x determined using 727 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4402
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0493P)^2^+0.3935P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1281
_reflns_Friedel_coverage         0.428
_reflns_Friedel_fraction_full    0.489
_reflns_Friedel_fraction_max     0.469
_reflns_number_gt                3143
_reflns_number_total             4402
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b03195_si_002.cif
_cod_data_source_block           mo_71012a
_cod_depositor_comments
'Adding full bibliography for 1547782--1547783.cif.'
_cod_original_cell_volume        1305.1(5)
_cod_database_code               1547783
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.931
_shelx_estimated_absorpt_t_max   0.990
_shelx_res_checksum              48235
_shelx_hkl_checksum              12090