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_1560017
_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            'C22 H26 O2'
_chemical_formula_weight         322.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_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                90
_cell_angle_beta                 99.927(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5885(4)
_cell_length_b                   8.3629(3)
_cell_length_c                   20.6387(7)
_cell_measurement_reflns_used    6556
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.5678
_cell_measurement_theta_min      4.4183
_cell_volume                     1800.21(11)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.1045
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26566
_diffrn_reflns_theta_full        66.70
_diffrn_reflns_theta_max         66.70
_diffrn_reflns_theta_min         4.42
_diffrn_source                   'Cu Ims'
_diffrn_source_type              'micro focus tube'
_exptl_absorpt_coefficient_mu    0.578
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_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    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.077
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.214
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3174
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0481P)^2^+0.7326P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1201
_reflns_number_gt                2277
_reflns_number_total             3174
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc06385a2.cif
_cod_data_source_block           glo9876
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1560015--1560017.cif.
;
_cod_database_code               1560017
_shelx_res_checksum              61594