Visible-light induced metal-free intramolecular reductive cyclisations of ketones with alkynes and allenes.
Tang, Nana; Zachmann, Raphael J.; Xie, Hui; Zheng, Jun; Breit, Bernhard; Chemical communications (Cambridge, England) 59 (2023) 2122–2125; doi:10.1039/d2cc06972e

data_7131214
_publ_section_title
;
 Visible-light induced metal-free intramolecular reductive cyclisations of
 ketones with alkynes and allenes.
;
_journal_issue                   15
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2122
_journal_page_last               2125
_journal_paper_doi               10.1039/d2cc06972e
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H21 N O3 S'
_chemical_formula_sum            'C19 H21 N O3 S'
_chemical_formula_weight         343.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method
;
FinalCif V104 by Daniel Kratzert, Freiburg 2022,
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2022-04-21 deposited with the CCDC.	2023-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.050(4)
_cell_length_b                   16.600(3)
_cell_length_c                   10.280(2)
_cell_measurement_reflns_used    9835
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.3845
_cell_measurement_theta_min      2.5425
_cell_volume                     3421.5(11)
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_collection
'Bruker BIS V6.2.15 Patch 4/2021-03-15 && APEX4 2021.10-0'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            228692
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.552
_diffrn_reflns_theta_min         1.593
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction:
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    1.333
_exptl_crystal_description       plate
_exptl_crystal_F_000             1456
_exptl_crystal_recrystallization_method
'Crystals were obtained at room temperature by slow diffusionof pentane into a solution of the compound dissolved indichloromethane by the aid of layering.'
_exptl_crystal_size_max          0.338
_exptl_crystal_size_mid          0.301
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 4455 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.297(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         10470
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0463P)^2^+1.1945P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0889
_reflns_Friedel_coverage         0.901
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                9869
_reflns_number_total             10470
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06972e2.cif
_cod_data_source_block           Breit_TN_343_a
_cod_depositor_comments
'Adding full bibliography for 7131213--7131214.cif.'
_cod_original_cell_volume        3421.4(11)
_cod_database_code               7131214
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.934
_shelx_estimated_absorpt_t_max   0.989
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_shelx_res_checksum              92666
_shelx_hkl_checksum              79615