Photoredox-enabled 1,2-dialkylation of α-substituted acrylates via Ireland–Claisen rearrangement
Kleinmans, Roman; Will, Leon E.; Schwarz, J. Luca; Glorius, Frank; Chemical Science 12 (2021) 2816–2822; doi:10.1039/D0SC06385A

data_1560016
_publ_section_title
;
 Photoredox-enabled 1,2-dialkylation of \a-substituted acrylates via
 Ireland--Claisen rearrangement
;
_journal_issue                   8
_journal_name_full               'Chemical Science'
_journal_page_first              2816
_journal_page_last               2822
_journal_paper_doi               10.1039/D0SC06385A
_journal_volume                  12
_journal_year                    2021
_chemical_formula_sum            'C12 H21 N O2 S'
_chemical_formula_weight         243.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           'APEX3 v2019.1-0'
_audit_update_record
;
2020-09-22 deposited with the CCDC.	2021-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                65.837(3)
_cell_angle_beta                 82.374(3)
_cell_angle_gamma                88.124(4)
_cell_formula_units_Z            2
_cell_length_a                   6.3005(3)
_cell_length_b                   10.5228(5)
_cell_length_c                   10.9791(5)
_cell_measurement_reflns_used    1477
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.0528
_cell_measurement_theta_min      4.4522
_cell_volume                     658.07(6)
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_collection       'APEX3 v2019.1-0'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON III Diffractometer'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0927
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9493
_diffrn_reflns_theta_full        66.63
_diffrn_reflns_theta_max         66.63
_diffrn_reflns_theta_min         4.45
_diffrn_source                   'Cu Ims'
_diffrn_source_type              'micro focus tube'
_exptl_absorpt_coefficient_mu    2.080
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   'Numerical Mu From Formula'
_exptl_absorpt_process_details
;
SADABS-2016/2 Bruker AXS area detector scaling and absorption correction.
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.198
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         2315
_refine_ls_number_restraints     281
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1147
_refine_ls_R_factor_gt           0.0643
_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^)+(0.1007P)^2^+0.1263P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1657
_refine_ls_wR_factor_ref         0.2026
_reflns_number_gt                1318
_reflns_number_total             2315
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc06385a2.cif
_cod_data_source_block           glo9874
_cod_depositor_comments
'Adding full bibliography for 1560015--1560017.cif.'
_cod_database_code               1560016
_shelx_res_checksum              46517