Stereoselective synthesis of C3-tetrasubstituted oxindoles via copper catalyzed asymmetric propargylation
Wang, Jiao-Mei; Zhao, Yu; Yao, Chang-Sheng; Zhang, Kai; RSC Advances 12 (2022) 26727–26732; doi:10.1039/D2RA04603B

data_7245521
_publ_section_title
;
 Stereoselective synthesis of C3-tetrasubstituted oxindoles via copper
 catalyzed asymmetric propargylation
;
_journal_issue                   41
_journal_name_full               'RSC Advances'
_journal_page_first              26727
_journal_page_last               26732
_journal_paper_doi               10.1039/D2RA04603B
_journal_volume                  12
_journal_year                    2022
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C22 H18 Br N O5'
_chemical_formula_sum            'C22 H18 Br N O5'
_chemical_formula_weight         456.28
_chemical_name_systematic        zk
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-25
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-06-26 deposited with the CCDC.	2022-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.928(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.738(6)
_cell_length_b                   14.001(10)
_cell_length_c                   8.854(6)
_cell_measurement_reflns_used    2796
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.431
_cell_measurement_theta_min      2.447
_cell_volume                     1018.3(12)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0738
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6231
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.878
_diffrn_reflns_theta_min         2.829
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.052
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1057 before and 0.0680 after correction.
The Ratio of minimum to maximum transmission is 0.6705.
The \l/2 correction factor is 0.00150.
;
_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    1.488
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 1110 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.054(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4333
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0473
_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^)+(0.0645P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1297
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    0.867
_reflns_Friedel_fraction_max     0.792
_reflns_number_gt                3144
_reflns_number_total             4333
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra04603b2.cif
_cod_data_source_block           ycs20220328chen_0m
_cod_database_code               7245521
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.684
_shelx_estimated_absorpt_t_min   0.684
_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. Restrained distances
 C21-C20
 1.54 with sigma of 0.02
 C20-C21
 1.54 with sigma of 0.02
3. Rigid bond restraints
 C20, C21
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C1, O1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 O4, C20
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(O4) \\sim Ueq, Uanis(C20) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
5.a Ternary CH refined with riding coordinates:
 C8(H8)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C20(H20A,H20B)
5.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C13(H13), C16(H16), C17(H17), C18(H18)
5.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C21(H21A,H21B,H21C)
5.e :
 C10(H10)
;
_shelx_res_checksum              9642
_olex2_submission_special_instructions 'No special instructions were received'