Trisubstituted alkenes with a single activator as dipolarophiles in a highly diastereo- and enantioselective [3+2] cycloaddition with vinyl epoxides under Pd-catalysis.
Du, Juan; Jiang, Yang-Jie; Suo, Jia-Jia; Wu, Wen-Qiong; Liu, Xiu-Yan; Chen, Di; Ding, Chang-Hua; Wei, Yin; Hou, Xue-Long; Chemical communications (Cambridge, England) 54 (2018) 13143–13146; doi:10.1039/c8cc07996j

data_7122539
_publ_section_title
;
 Trisubstituted alkenes with a single activator as dipolarophiles in a
 highly diastereo- and enantioselective [3+2] cycloaddition with vinyl
 epoxides under Pd-catalysis.
;
_journal_issue                   93
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              13143
_journal_page_last               13146
_journal_paper_doi               10.1039/c8cc07996j
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H23.4 Br N O2'
_chemical_formula_weight         353.68
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-09-30 deposited with the CCDC.
2018-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            20
_cell_length_a                   10.2614(10)
_cell_length_b                   21.747(2)
_cell_length_c                   40.341(4)
_cell_measurement_reflns_used    3971
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      39.757
_cell_measurement_theta_min      4.389
_cell_volume                     9002.3(15)
_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 0.974
_diffrn_measured_fraction_theta_max 1.000
_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  0.1163
_diffrn_reflns_av_unetI/netI     0.1602
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            50143
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.781
_exptl_absorpt_coefficient_mu    2.287
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             3668
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
; 
 Flack x determined using 2040 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.010(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     964
_refine_ls_number_reflns         15865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.1936
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0540P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1641
_reflns_Friedel_coverage         0.813
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                6133
_reflns_number_total             15865
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc07996j2.cif
_cod_data_source_block           cd17129
_cod_depositor_comments
'Adding full bibliography for 7122537--7122539.cif.'
_cod_original_cell_volume        9002.2(15)
_cod_original_formula_sum        'C17 H23.40 Br N O2'
_cod_database_code               7122539
_shelx_estimated_absorpt_t_min   0.684
_shelx_estimated_absorpt_t_max   0.838
_shelxl_version_number           2013-4
_shelx_res_checksum              5443
_shelx_hkl_checksum              95528