Discovery of Oxygen α-Nucleophilic Addition to α,β-Unsaturated Amides Catalyzed by Redox-Neutral Organic Photoreductant.
Luan, Zi-Hong; Qu, Jian-Ping; Kang, Yan-Biao; Journal of the American Chemical Society 142 (2020) 20942–20947; doi:10.1021/jacs.0c10707

data_4135387
_publ_section_title
;
 Discovery of Oxygen \a-Nucleophilic Addition to \a,\b-Unsaturated Amides
 Catalyzed by Redox-Neutral Organic Photoreductant.
;
_journal_issue                   50
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              20942
_journal_page_last               20947
_journal_paper_doi               10.1021/jacs.0c10707
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C33 H23 N'
_chemical_formula_sum            'C33 H23 N'
_chemical_formula_weight         433.52
_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_creation_date             2020-10-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.838(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6755(7)
_cell_length_b                   5.2979(3)
_cell_length_c                   31.0800(14)
_cell_measurement_reflns_used    1414
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      67.9400
_cell_measurement_theta_min      5.2240
_cell_volume                     2249.0(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_unetI/netI     0.1095
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            8097
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.235
_diffrn_reflns_theta_min         3.470
_exptl_absorpt_coefficient_mu    0.561
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.00117(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4164
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1346
_refine_ls_R_factor_gt           0.0719
_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^)+(0.0352P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1394
_refine_ls_wR_factor_ref         0.1787
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2178
_reflns_number_total             4164
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c10707_si_005.cif
_cod_data_source_block           lzh-cbz6
_cod_depositor_comments
'Adding full bibliography for 4135385--4135388.cif.'
_cod_original_cell_volume        2249.01(19)
_cod_database_code               4135387
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.916
_shelx_estimated_absorpt_t_min   0.891
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C9(H9), C18(H18), C6(H6), C4(H4), C3(H3), C11(H11),
 C5(H5), C19(H19), C24(H24), C22(H22), C23(H23), C26(H26), C25(H25), C32(H32),
 C30(H30), C28(H28), C31(H31), C29(H29)
2.b Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C)
;
_olex2_submission_special_instructions 'No special instructions were received'