Visible-light excitation of iminium ions enables the enantioselective catalytic beta-alkylation of enals
Mattia Silvi; Charlie Verrier; Yannick P. Rey; Luca Buzzetti; Paolo Melchiorre; Nature Chemistry 9 (2017) 868–873; doi:10.1038/nchem.2748

data_1551891
_publ_section_title
;
 Visible-light excitation of iminium ions enables the enantioselective
 catalytic beta-alkylation of enals
;
_journal_name_full               'Nature Chemistry'
_journal_page_first              868
_journal_page_last               873
_journal_paper_doi               10.1038/nchem.2748
_journal_volume                  9
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C42 H46 B F18 N O2 Si'
_chemical_formula_weight         977.70
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6934(3)
_cell_length_b                   17.4932(4)
_cell_length_c                   24.2485(6)
_cell_measurement_reflns_used    22003
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      30.0090
_cell_measurement_theta_min      2.0610
_cell_volume                     4536.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.37f (Rigaku OD, 2015)'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_data_reduction        'CrysAlisPro 1.171.38.37f (Rigaku OD, 2015)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    Sir2011
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            59593
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.066
_diffrn_reflns_theta_min         2.044
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_current           24
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       block
_exptl_crystal_F_000             2008
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.778
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Flack x determined using 3674 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.579
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     965
_refine_ls_number_reflns         13385
_refine_ls_number_restraints     792
_refine_ls_restrained_S_all      1.673
_refine_ls_R_factor_all          0.1037
_refine_ls_R_factor_gt           0.0783
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2159
_refine_ls_wR_factor_ref         0.2302
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.891
_reflns_number_gt                9718
_reflns_number_total             13385
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            nchem.2748-s4.cif
_cod_data_source_block           CV_iminiumYCF
_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 built-in table derived
from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the built-in table derived from
the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        4535.98(19)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1551891
_shelx_estimated_absorpt_t_min   0.938
_shelx_estimated_absorpt_t_max   0.976
_shelxl_version_number           2014-3
_shelx_res_checksum              26529
_shelx_hkl_checksum              76171