Enantioselective crossed intramolecular [2+2] photocycloaddition reactions mediated by a chiral chelating Lewis acid
Rigotti, Thomas; Schwinger, Daniel P.; Graßl, Raphaela; Jandl, Christian; Bach, Thorsten; Chemical Science 13 (2022) 2378–2384; doi:10.1039/D2SC00113F

data_1566247
_publ_section_title
;
 Enantioselective crossed intramolecular [2+2] photocycloaddition
 reactions mediated by a chiral chelating Lewis acid
;
_journal_issue                   8
_journal_name_full               'Chemical Science'
_journal_page_first              2378
_journal_page_last               2384
_journal_paper_doi               10.1039/D2SC00113F
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_compound_source        'see text'
_chemical_formula_moiety         '2(C15 H17 N3 O5 S)'
_chemical_formula_sum            'C15 H17 N3 O5 S'
_chemical_formula_weight         351.38
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2021-12-22 deposited with the CCDC.	2022-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.951(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5937(6)
_cell_length_b                   22.424(2)
_cell_length_c                   10.7128(11)
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.1651
_cell_measurement_theta_min      2.6430
_cell_volume                     1568.7(3)
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_collection       'APEX III Control Software (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011), enCIFer (Allen, 2014)'
_computing_structure_refinement
'SHELXL (Sheldrick, 2018), SHELXLE (Huebschle, 2011)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 ' Bruker Photon-100 CMOS '
_diffrn_detector_area_resol_mean 16
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       ' \k-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker D8 Venture '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_radiation_monochromator  'Helios optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'TXS rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            54792
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         26.73
_diffrn_reflns_theta_min         2.64
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2, Bruker, 2016'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.207
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.606
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.017(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         6656
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0300
_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^)+(0.0417P)^2^+0.6965P] WHERE P=(FO^2^+2FC^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0796
_reflns_number_gt                6512
_reflns_number_total             6656
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            d2sc00113f2.cif
_cod_data_source_block           compound_7
_cod_depositor_comments          'Adding full bibliography for 1566247.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1566247
_shelx_res_checksum              30204
_shelx_hkl_checksum              6556