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_1568422
_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            'C27 H24 F3 N3 O2 S'
_chemical_formula_weight         511.55
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc2cmsjb
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4828(3)
_cell_length_b                   18.3087(7)
_cell_length_c                   18.4701(7)
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.60
_cell_measurement_theta_min      2.21
_cell_volume                     2530.41(17)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.934
_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  0.0301
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            43297
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.461
_diffrn_reflns_theta_min         2.205
_diffrn_source                   'micro source 3.0'
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G. M., sadabs (2015). Acta Cryst. C71, 3-8.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       needle
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.352
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.128
_exptl_transmission_factor_max   0.7464
_exptl_transmission_factor_min   0.6706
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
; 
 Flack x determined using 2685 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.004(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         8307
_refine_ls_number_restraints     804
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0616P)^2^+0.1908P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1096
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.882
_reflns_number_gt                6880
_reflns_number_total             8307
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc07021a2.cif
_cod_data_source_block           hkl_a
_cod_depositor_comments
'Adding full bibliography for 1568422--1568423.cif.'
_cod_database_code               1568422
_publcif_datablock.id            {e007c1c8-273a-4d2f-a8c1-4d929db8c2cb}
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.939
_shelx_estimated_absorpt_t_max   0.977
_shelx_res_checksum              27542
_publcif_funding_html
;
;