Visible-light photoredox-catalyzed three-component radical alkyl-acylation of [1.1.1]propellane.
Liu, Lanqin; Guo, Shengkun; Chen, Chengjun; Shen, Xiaoyu; Chen, Xiaoyun; Yu, Huaguang; Han, Ying; Sun, Qiu; Zhu, Shaoqun; Hou, Hong; Organic & biomolecular chemistry 22 (2024) 9192–9196; doi:10.1039/d4ob01549e

data_7160189
_publ_section_title
;
 Visible-light photoredox-catalyzed three-component radical
 alkyl-acylation of [1.1.1]propellane.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9192
_journal_page_last               9196
_journal_paper_doi               10.1039/d4ob01549e
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C17 H22 O S'
_chemical_formula_sum            'C17 H22 O S'
_chemical_formula_weight         274.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2hpq75
_audit_creation_date             2023-12-16
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-12-16 deposited with the CCDC.	2024-10-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.669(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4888(10)
_cell_length_b                   17.779(3)
_cell_length_c                   13.5432(19)
_cell_measurement_reflns_used    7089
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      24.535
_cell_measurement_theta_min      2.291
_cell_volume                     1530.1(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23519
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.512
_diffrn_reflns_theta_min         2.291
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1329 before and 0.0458 after correction.
The Ratio of minimum to maximum transmission is 0.9347.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3512
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1067
_refine_ls_R_factor_gt           0.0587
_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^)+(0.0727P)^2^+0.6262P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1666
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2144
_reflns_number_total             3512
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01549e2.cif
_cod_data_source_block           gsk123
_cod_depositor_comments          'Adding full bibliography for 7160189.cif.'
_cod_database_code               7160189
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B),
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              93494
_shelx_hkl_checksum              65366
_olex2_submission_special_instructions 'No special instructions were received'