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_7122538
_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            'C20 H21 Cl N2 O4'
_chemical_formula_weight         388.84
_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            16
_cell_length_a                   10.4038(4)
_cell_length_b                   20.5233(6)
_cell_length_c                   37.6117(11)
_cell_measurement_reflns_used    9795
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      43.820
_cell_measurement_theta_min      4.474
_cell_volume                     8030.9(5)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0546
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            43420
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         2.383
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6473
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             3264
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
; 
 Flack x determined using 3104 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     982
_refine_ls_number_reflns         14873
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0494
_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^)+(0.0763P)^2^+0.0643P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1509
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                8904
_reflns_number_total             14873
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc07996j2.cif
_cod_data_source_block           mo_d8v18616_0m
_cod_depositor_comments
'Adding full bibliography for 7122537--7122539.cif.'
_cod_database_code               7122538
_shelx_estimated_absorpt_t_min   0.962
_shelx_estimated_absorpt_t_max   0.974
_shelxl_version_number           2013-4
_shelx_res_checksum              88630
_shelx_hkl_checksum              67974