NickelII-catalyzed asymmetric photoenolization/Mannich reaction of (2-alkylphenyl) ketones
Yang, Liangkun; Li, Wang-Yuren; Hou, Liuzhen; Zhan, Tangyu; Cao, Weidi; Liu, Xiaohua; Feng, Xiaoming; Chemical Science 13 (2022) 8576–8582; doi:10.1039/D2SC02721F

data_1567157
_publ_section_title
;
 NickelII-catalyzed asymmetric photoenolization/Mannich reaction of
 (2-alkylphenyl) ketones
;
_journal_issue                   29
_journal_name_full               'Chemical Science'
_journal_page_first              8576
_journal_page_last               8582
_journal_paper_doi               10.1039/D2SC02721F
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H25 N O4 S'
_chemical_formula_sum            'C30 H25 N O4 S'
_chemical_formula_weight         495.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2022-05-11 deposited with the CCDC.	2022-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.6145(2)
_cell_length_b                   18.9746(4)
_cell_length_c                   26.9615(6)
_cell_measurement_reflns_used    9218
_cell_measurement_temperature    175(2)
_cell_measurement_theta_max      80.19
_cell_measurement_theta_min      2.85
_cell_volume                     4918.62(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      175(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            32840
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.527
_diffrn_reflns_theta_min         2.848
_exptl_absorpt_coefficient_mu    1.476
_exptl_absorpt_correction_T_max  0.9700
_exptl_absorpt_correction_T_min  0.5923
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       flake
_exptl_crystal_F_000             2080
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, PE'
_exptl_crystal_size_max          0.426
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
; 
 Flack x determined using 4228 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.030(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     651
_refine_ls_number_reflns         10276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0319
_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^)+(0.0398P)^2^+0.7264P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0812
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.931
_reflns_number_gt                9982
_reflns_number_total             10276
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc02721f2.cif
_cod_data_source_block           way020
_cod_depositor_comments
;
Adding full bibliography for 1567156--1567157.cif.

2025-06-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C60 H50 N2 O8 S2'
_cod_original_formula_weight         991.14
_cod_original_formula_moiety         '2(C30 H25 N O4 S)'
_cod_original_formula_units_Z            4
_cod_database_code               1567157
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.572
_shelx_estimated_absorpt_t_max   0.874
_shelx_res_checksum              47391
_shelx_hkl_checksum              14782