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_7060700
_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         'C27 H21 Br N2 O3'
_chemical_formula_sum            'C27 H21 Br N2 O3'
_chemical_formula_weight         501.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-10-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-16 deposited with the CCDC.	2021-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1785(14)
_cell_length_b                   25.516(4)
_cell_length_c                   12.111(2)
_cell_measurement_reflns_used    9874
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.26
_cell_measurement_theta_min      2.93
_cell_volume                     2527.4(7)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            31059
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.413
_diffrn_reflns_theta_min         2.927
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.656
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1507 before and 0.0791 after correction.
The Ratio of minimum to maximum transmission is 0.5498.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.799
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
;
 Flack x determined using 1367 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.052(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5674
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.1140
_refine_ls_R_factor_gt           0.0776
_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^)+(0.1618P)^2^+0.7219P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2335
_refine_ls_wR_factor_ref         0.2613
_reflns_Friedel_coverage         0.886
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                3876
_reflns_number_total             5674
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj00960e2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7060699--7060700.cif.'
_cod_original_cell_volume        2527.3(7)
_cod_database_code               7060700
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.814
_shelx_estimated_absorpt_t_min   0.682
_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. Uiso/Uaniso restraints and constraints
Uanis(C18) \\sim Ueq, Uanis(C17) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C11(H11), C13(H13), C7(H7), C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C22(H22), C24(H24), C20(H20), C25(H25), C23(H23), C5(H5),
 C2(H2A), C16(H16), C4(H4), C19(H19), C3(H3), C18(H18), C17(H17)
;
_shelx_res_checksum              17768
_olex2_submission_special_instructions 'No special instructions were received'