Direct Visible-Light-Excited Asymmetric Lewis Acid Catalysis of Intermolecular [2+2] Photocycloadditions.
Huang, Xiaoqiang; Quinn, Taylor R.; Harms, Klaus; Webster, Richard D.; Zhang, Lilu; Wiest, Olaf; Meggers, Eric; Journal of the American Chemical Society 139 (2017) 9120–9123; doi:10.1021/jacs.7b04363

data_4131340
_publ_section_title
;
 Direct Visible-Light-Excited Asymmetric Lewis Acid Catalysis of
 Intermolecular [2+2] Photocycloadditions.
;
_journal_issue                   27
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9120
_journal_page_last               9123
_journal_paper_doi               10.1021/jacs.7b04363
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H23 Br N2 O'
_chemical_formula_sum            'C24 H23 Br N2 O'
_chemical_formula_weight         435.35
_chemical_name_common            hxqG7
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2276(6)
_cell_length_b                   10.0974(9)
_cell_length_c                   33.032(3)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      25.2416
_cell_measurement_theta_min      2.3641
_cell_volume                     2077.1(3)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'XT V2014/1 (Bruker AXS Inc., 2014)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 7.9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            19907
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.270
_diffrn_reflns_theta_min         2.364
_diffrn_source                   'microfocus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.995
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS 2016/2: 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    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.755
_refine_diff_density_min         -0.830
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
; 
 Flack x determined using 1341 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.004(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3772
_refine_ls_number_restraints     183
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0397
_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^)+(0.0475P)^2^+1.5917P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.0975
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3515
_reflns_number_total             3772
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b04363_si_002.cif
_cod_data_source_block           hxqG7_0m
_cod_database_code               4131340
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.363
_shelx_estimated_absorpt_t_max   0.886
_shelx_res_checksum              37754
_shelx_hkl_checksum              54189