Pd(0)-catalysed asymmetric reductive Heck-type cyclization of (Z)-1-iodo-1,6-diene: enantioselective synthesis of quaternary tetrahydropyridines
Hou, Longlei; Yuan, Yuejie; Tong, Xiaofeng; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB00762K

data_7155576
_publ_section_title
;
 Pd(0)-catalysed asymmetric reductive Heck-type cyclization of
 (Z)-1-iodo-1,6-diene: enantioselective synthesis of quaternary
 tetrahydropyridines
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB00762K
_journal_year                    2017
_chemical_formula_sum            'C27 H28 Br N O3 S'
_chemical_formula_weight         526.47
_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_block_doi                 10.5517/ccdc.csd.cc1nq31j
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-03-28 deposited with the CCDC.
2017-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.286(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.2079(18)
_cell_length_b                   10.4253(16)
_cell_length_c                   11.4032(19)
_cell_measurement_reflns_used    5243
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.52
_cell_volume                     1203.7(3)
_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 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0512
_diffrn_reflns_av_unetI/netI     0.0829
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8311
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.003
_diffrn_reflns_theta_max         25.003
_diffrn_reflns_theta_min         2.657
_exptl_absorpt_coefficient_mu    1.824
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details
;
 Flack x determined using 1511 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.092(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4132
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0343P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.0978
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_full    0.941
_reflns_Friedel_fraction_max     0.941
_reflns_number_gt                3752
_reflns_number_total             4132
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00762k2.cif
_cod_data_source_block           20170314cz_0m_b
_cod_database_code               7155576
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.648
_shelx_estimated_absorpt_t_max   0.690
_shelx_res_checksum              2238