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_4514619
_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_absolute_configuration ad
_chemical_compound_source        synthetic
_chemical_formula_moiety         'C24 H35 I1 O1'
_chemical_formula_sum            'C24 H35 I O'
_chemical_formula_weight         466.45
_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_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2018-09-13
_audit_creation_method           CRYSTALS_ver_14.61_build_6236
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.30332(4)
_cell_length_b                   11.85008(9)
_cell_length_c                   28.71209(18)
_cell_measurement_reflns_used    27068
_cell_measurement_temperature    100
_cell_measurement_theta_max      36
_cell_measurement_theta_min      2
_cell_volume                     2144.65(3)
_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 0.955
_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  0.0577
_diffrn_reflns_av_sigmaI/netI    0.0848
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            46658
_diffrn_reflns_theta_full        32.119
_diffrn_reflns_theta_max         36.089
_diffrn_reflns_theta_min         1.802
_diffrn_source                   Synchrotron
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.503
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         2.06
_refine_diff_density_min         -1.18
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 4318 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   -0.036(8)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         10425
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.0007857
_refine_ls_shift/su_mean         0.0000423
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.44P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0967
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.0967
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              48
_reflns_limit_l_min              0
_reflns_number_gt                9448
_reflns_number_total             10443
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.01
_oxford_diffrn_Wilson_scale      0.14
_oxford_refine_ls_r_factor_ref   0.0402
_oxford_refine_ls_scale          2.813(16)
_oxford_reflns_number_all        10425
_oxford_structure_analysis_title 105eaa18
_cod_data_source_file            cs9b03190_si_002.cif
_cod_data_source_block           87
_cod_depositor_comments
;
The following automatic conversions were performed:

'_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_cell_volume        2144.64(3)
_cod_original_formula_sum        'C24 H35 I1 O1'
_cod_database_code               4514619
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_hooft_y                  -0.041(7)
_oxford_bijvoet_difference       -0.036(8)
_oxford_refined_flack_x          -0.028(14)