A General Route to Bicyclo[1.1.1]pentanes through Photoredox Catalysis
Nugent, Jeremy; Arroniz, Carlos; Shire, Bethany R.; Sterling, Alistair J.; Pickford, Helena D.; Wong, Marie L. J.; Mansfield, Steven J.; Caputo, Dimitri F. J.; Owen, Benjamin; Mousseau, James J.; Duarte, Fernanda; Anderson, Edward A.; ACS Catalysis 9 (2019) 9568–; doi:10.1021/acscatal.9b03190

data_4514618
_publ_section_title
;
 A General Route to Bicyclo[1.1.1]pentanes through Photoredox Catalysis
;
_journal_issue                   10
_journal_name_full               'ACS Catalysis'
_journal_page_first              9568
_journal_paper_doi               10.1021/acscatal.9b03190
_journal_volume                  9
_journal_year                    2019
_chemical_compound_source        synthetic
_chemical_formula_moiety         'C20 H26 I1 N1 O2 S1'
_chemical_formula_sum            'C20 H26 I N O2 S'
_chemical_formula_weight         471.40
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2019-03-21
_audit_creation_method           CRYSTALS_ver_14.61_build_6236
_cell_angle_alpha                90
_cell_angle_beta                 91.862(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2416(7)
_cell_length_b                   20.4922(11)
_cell_length_c                   7.9382(4)
_cell_measurement_reflns_used    5100
_cell_measurement_temperature    100
_cell_measurement_theta_max      24
_cell_measurement_theta_min      2
_cell_volume                     1990.30(19)
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_collection       'Diamond GDA'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Pilatus 2M'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device
'Pilatus 2M detector on Crystal Logic diffractometer'
_diffrn_measurement_device_type  'Photon counting area detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  Synchrotron
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.68890
_diffrn_reflns_av_R_equivalents  0.172
_diffrn_reflns_av_sigmaI/netI    0.434
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            28866
_diffrn_reflns_theta_full        25.584
_diffrn_reflns_theta_max         25.584
_diffrn_reflns_theta_min         1.613
_diffrn_source                   Synchrotron
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.727
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.49
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.085
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.005
_refine_diff_density_max         3.00
_refine_diff_density_min         -1.52
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9900
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4070
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1421
_refine_ls_R_factor_gt           0.0861
_refine_ls_shift/su_max          0.0002202
_refine_ls_shift/su_mean         0.0000137
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.03P)^2^ +10.94P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2630
_refine_ls_wR_factor_gt          0.2199
_refine_ls_wR_factor_ref         0.2630
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              25
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                2314
_reflns_number_total             4086
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.26
_oxford_diffrn_Wilson_scale      1.85
_oxford_refine_ls_r_factor_ref   0.1421
_oxford_refine_ls_scale          0.835(6)
_oxford_reflns_number_all        4070
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 026eaa18
_cod_data_source_file            cs9b03190_si_002.cif
_cod_data_source_block           77
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Other' changed to 'other'
according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C20 H26 I1 N1 O2 S1'
_cod_database_code               4514618