Vicinal stereocenters <i>via</i> asymmetric allylic alkylation and Cope rearrangement: a straightforward route to functionally and stereochemically rich heterocycles.
Nilova, Aleksandra; Mannchen, Michael D.; Noel, Abdias N.; Semenova, Evgeniya; Grenning, Alexander J.; Chemical science 14 (2023) 2755–2762; doi:10.1039/d2sc07021a

data_1568423
_publ_section_title
;
 Vicinal stereocenters <i>via</i> asymmetric allylic alkylation and Cope
 rearrangement: a straightforward route to functionally and
 stereochemically rich heterocycles.
;
_journal_issue                   10
_journal_name_full               'Chemical science'
_journal_page_first              2755
_journal_page_last               2762
_journal_paper_doi               10.1039/d2sc07021a
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H24 Cl N O4 S'
_chemical_formula_weight         445.94
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-07-30 deposited with the CCDC.	2023-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.4170(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.1508(4)
_cell_length_b                   6.3344(2)
_cell_length_c                   15.0399(5)
_cell_measurement_reflns_used    8580
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.44
_cell_measurement_theta_min      2.48
_cell_volume                     1048.01(6)
_computing_cell_refinement       'Bruker APEX3 (Bruker, 2019)'
_computing_data_collection       'Bruker APEX3 (Bruker, 2019)'
_computing_data_reduction        'Bruker Apex3 SAINT (Bruker, 2019)'
_computing_molecular_graphics    'XP in SHELXTL-plus, Bruker 2019'
_computing_publication_material  'SHELXL2015, Sheldrick, G. M. 2019'
_computing_structure_refinement  'SHELXL2015, Sheldrick G. M. 2019'
_computing_structure_solution    'SHELXL2015, Sheldrick G. M. 2019'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'D8 Venture with PHOTON III'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22288
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.747
_diffrn_reflns_theta_min         1.851
_diffrn_source                   'micro source 3.0'
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G. M., sadabs (2015). Acta Cryst. C71, 3-8.'
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       plate
_exptl_crystal_F_000             468
_exptl_transmission_factor_max   0.5657
_exptl_transmission_factor_min   0.4626
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
; 
 Flack x determined using 2424 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         6791
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0345
_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^)+(0.0389P)^2^+0.1045P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0849
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.834
_reflns_number_gt                6055
_reflns_number_total             6791
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc07021a2.cif
_cod_data_source_block           lova3
_cod_depositor_comments
'Adding full bibliography for 1568422--1568423.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1568423
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              32398