Rhodium-catalyzed highly diastereoselective intramolecular [4 + 2] cycloaddition of 1,3-disubstituted allene-1,3-dienes
Han, Yulin; Ma, Shengming; Organic Chemistry Frontiers 5 (2018) 2680–; doi:10.1039/C8QO00650D

data_1554375
_publ_section_title
;
 Rhodium-catalyzed highly diastereoselective intramolecular [4 + 2]
 cycloaddition of 1,3-disubstituted allene-1,3-dienes
;
_journal_issue                   18
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2680
_journal_paper_doi               10.1039/C8QO00650D
_journal_volume                  5
_journal_year                    2018
_chemical_formula_sum            'C18 H23 N O2 S'
_chemical_formula_weight         317.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-06-13 deposited with the CCDC.
2018-07-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.747(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6868(14)
_cell_length_b                   20.200(3)
_cell_length_c                   8.0112(10)
_cell_measurement_reflns_used    2189
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.042
_cell_measurement_theta_min      4.384
_cell_volume                     1693.2(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.999
_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  0.0374
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
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_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9268
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.998
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_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       prismatic
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_refine_diff_density_max         0.272
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2981
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0661P)^2^+0.4888P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1316
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2365
_reflns_number_total             2981
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00650d2.cif
_cod_data_source_block           cd17234
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1554375
_shelx_estimated_absorpt_t_min   0.961
_shelx_estimated_absorpt_t_max   0.975
_shelxl_version_number           2013-4
_shelx_res_checksum              20421
_shelx_hkl_checksum              35074