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_1551890
_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            'C33 H26 O2 S'
_chemical_formula_weight         486.60
_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_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 97.4465(18)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   29.4752(19)
_cell_length_b                   8.8183(6)
_cell_length_c                   37.823(2)
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.23
_cell_volume                     9748.1(10)
_computing_cell_refinement       'Bruker APEX2 v2014.9-0'
_computing_data_collection       'Bruker APEX2 v2014.9-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    Sir2011
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            90192
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.470
_diffrn_reflns_theta_min         0.697
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_current           0.6
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Bruker APEX DUO'
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             4096
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details
;
 Flack x determined using 9909 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2593
_refine_ls_number_reflns         34785
_refine_ls_number_restraints     213
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0862
_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^)+(0.0001P)^2^+54.0936P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1829
_refine_ls_wR_factor_ref         0.1935
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_full    0.936
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                26903
_reflns_number_total             34785
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            nchem.2748-s3.cif
_cod_data_source_block           mo_BUZ320-b_0m
_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 'Monoclinic' was changed to
'monoclinic' 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        9748.0(11)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1551890
_shelx_estimated_absorpt_t_min   0.960
_shelx_estimated_absorpt_t_max   0.995
_shelxl_version_number           2014-3
_shelx_res_checksum              11983
_shelx_hkl_checksum              20225