Rapid umpolung Michael addition of isatin N,N′-cyclic azomethine imine 1,3-dipoles with chalcones
Yue, Guizhou; Jiang, Dan; Dou, Zhengjie; Li, Sicheng; Feng, Juhua; Zhang, Li; Chen, Huabao; Yang, Chunping; Yin, Zhongqiong; Song, Xu; Liang, Xiaoxia; Wang, Xianxiang; Lu, Cuifen; New Journal of Chemistry 45 (2021) 11712–11718; doi:10.1039/D1NJ00960E

data_7060699
_publ_section_title
;
 Rapid umpolung Michael addition of isatin N,N&#x2032;-cyclic azomethine
 imine 1,3-dipoles with chalcones
;
_journal_issue                   26
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              11712
_journal_page_last               11718
_journal_paper_doi               10.1039/D1NJ00960E
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C26 H20 Br N3 O3'
_chemical_formula_sum            'C26 H20 Br N3 O3'
_chemical_formula_weight         502.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-11-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-28 deposited with the CCDC.	2021-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.378(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6861(14)
_cell_length_b                   21.538(3)
_cell_length_c                   13.065(2)
_cell_measurement_reflns_used    9902
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.165
_cell_measurement_theta_min      3.124
_cell_volume                     2305.8(6)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            48525
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.613
_diffrn_reflns_theta_min         3.124
_exptl_absorpt_coefficient_mu    1.816
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0876 before and 0.0511 after correction.
The Ratio of minimum to maximum transmission is 0.7009.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.624
_refine_diff_density_min         -1.607
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0547
_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^)+(0.0559P)^2^+3.5708P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1412
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4007
_reflns_number_total             5330
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj00960e2.cif
_cod_data_source_block           222
_cod_depositor_comments
'Adding full bibliography for 7060699--7060700.cif.'
_cod_database_code               7060699
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.812
_shelx_estimated_absorpt_t_min   0.670
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N1(H1), C17(H17), C24(H24), C11(H11), C14(H14), C19(H19), C16(H16),
 C6(H6), C2(H2), C25(H25), C15(H15), C18(H18), C12(H12), C13(H13), C3(H3A),
 C5(H5)
;
_shelx_res_checksum              81355
_olex2_submission_special_instructions 'No special instructions were received'