Highly diastereoselective annulation of 2-substituted 3-nitro-2H-chromenes with hemicurcuminoids and curcuminoids via a double and triple Michael reaction cascade
Zimnitskiy, Nikolay S.; Barkov, Alexey Yu.; Kochnev, Ivan A.; Kutyashev, Igor B.; Korotaev, Vladislav Yu.; Sosnovskikh, Vyacheslav Ya.; New Journal of Chemistry 46 (2022) 16047–16057; doi:10.1039/D2NJ02019J

data_7061671
_publ_section_title
;
 Highly diastereoselective annulation of 2-substituted
 3-nitro-2H-chromenes with hemicurcuminoids and curcuminoids via a double
 and triple Michael reaction cascade
;
_journal_issue                   33
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16047
_journal_page_last               16057
_journal_paper_doi               10.1039/D2NJ02019J
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C33 H22 Cl2 F3 N3 O3'
_chemical_formula_sum            'C33 H22 Cl2 F3 N3 O3'
_chemical_formula_weight         636.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-02-24 deposited with the CCDC.	2022-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                79.867(8)
_cell_angle_beta                 78.202(7)
_cell_angle_gamma                85.035(7)
_cell_formula_units_Z            2
_cell_length_a                   8.4663(7)
_cell_length_b                   12.6932(12)
_cell_length_c                   13.8600(13)
_cell_measurement_reflns_used    1972
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.9310
_cell_measurement_theta_min      3.5780
_cell_volume                     1433.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     51.00  77.00   1.00   30.00    --   22.52-138.00   1.00   26
  2  \w     18.00  43.00   1.00   30.00    --   22.52-132.00 177.00   25
  3  \w    -86.00 -20.00   1.00   30.00    --  -23.92 132.00-113.00   66
  4  \w    -89.00 -58.00   1.00   30.00    --  -23.92 138.00  63.00   31
  5  \w     -3.00  92.00   1.00   30.00    --   22.52  38.00-180.00   95
  6  \w      1.00  91.00   1.00   30.00    --   22.52  57.00 -90.00   90
  7  \w    -46.00  48.00   1.00   30.00    --   22.52 -38.00   0.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0282104000
_diffrn_orient_matrix_UB_12      -0.0354731000
_diffrn_orient_matrix_UB_13      0.0446660000
_diffrn_orient_matrix_UB_21      0.0144006000
_diffrn_orient_matrix_UB_22      0.0381890000
_diffrn_orient_matrix_UB_23      0.0284953000
_diffrn_orient_matrix_UB_31      -0.0796386000
_diffrn_orient_matrix_UB_32      0.0226825000
_diffrn_orient_matrix_UB_33      0.0003330000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0961
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.848
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13615
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.915
_diffrn_reflns_theta_min         3.479
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       prism
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0046(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     430
_refine_ls_number_reflns         7704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1474
_refine_ls_R_factor_gt           0.0604
_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^)+(0.0581P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1880
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3497
_reflns_number_total             7704
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj02019j2.cif
_cod_data_source_block           exp_1002
_cod_depositor_comments
'Adding full bibliography for 7061667--7061671.cif.'
_cod_database_code               7061671
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.882
_reflns_odcompleteness_completeness 98.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
 C26(H26), C27(H27), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.191
_oxdiff_exptl_absorpt_empirical_full_min 0.850