Copper-Catalyzed Radical 1,4-Difunctionalization of 1,3-Enynes with Alkyl Diacyl Peroxides and N-Fluorobenzenesulfonimide.
Zhu, Xiaotao; Deng, Weili; Chiou, Mong-Feng; Ye, Changqing; Jian, Wujun; Zeng, Yuehua; Jiao, Yihang; Ge, Liang; Li, Yajun; Zhang, Xinhao; Bao, Hongli; Journal of the American Chemical Society 141 (2019) 548–559; doi:10.1021/jacs.8b11499

data_4133592
_publ_section_title
;
 Copper-Catalyzed Radical 1,4-Difunctionalization of 1,3-Enynes with Alkyl
 Diacyl Peroxides and N-Fluorobenzenesulfonimide.
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              548
_journal_page_last               559
_journal_paper_doi               10.1021/jacs.8b11499
_journal_volume                  141
_journal_year                    2019
_chemical_formula_sum            'C27 H24 N2 O4 S2'
_chemical_formula_weight         504.60
_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
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.66(2)
_cell_length_b                   10.256(12)
_cell_length_c                   25.26(3)
_cell_measurement_reflns_used    7141
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.4231
_cell_measurement_theta_min      2.6147
_cell_volume                     5352(10)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 91.8000
_diffrn_measured_fraction_theta_max 26.4231
_diffrn_measurement_device_type  'Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1148
_diffrn_reflns_av_unetI/netI     0.3365
_diffrn_reflns_Laue_measured_fraction_full 0.929
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            13706
_diffrn_reflns_point_group_measured_fraction_full 0.548
_diffrn_reflns_point_group_measured_fraction_max 0.531
_diffrn_reflns_theta_full        26.4231
_diffrn_reflns_theta_max         26.440
_diffrn_reflns_theta_min         2.742
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       Prism
_exptl_crystal_F_000             2112
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.815
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.33(17)
_refine_ls_extinction_coef       0.019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   0.908
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     632
_refine_ls_number_reflns         5843
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      0.911
_refine_ls_R_factor_all          0.1353
_refine_ls_R_factor_gt           0.0942
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1647P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2296
_refine_ls_wR_factor_ref         0.2934
_reflns_Friedel_coverage         0.136
_reflns_Friedel_fraction_full    0.147
_reflns_Friedel_fraction_max     0.130
_reflns_number_gt                2408
_reflns_number_total             5843
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b11499_si_007.cif
_cod_data_source_block           38b
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 

2020-08-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        5351(11)
_cod_original_formula_sum        'C54 H48 N4 O8 S4'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     1009.20
_cod_database_code               4133592
_shelx_shelxl_version_number     2017/1
_shelx_res_checksum              31259
_shelx_hkl_checksum              18095