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_7061667
_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         'C32 H25 N O5'
_chemical_formula_sum            'C32 H25 N O5'
_chemical_formula_weight         503.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-09-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2022-02-24 deposited with the CCDC.	2022-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.431(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4214(10)
_cell_length_b                   12.2255(9)
_cell_length_c                   14.5032(10)
_cell_measurement_reflns_used    2796
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.3950
_cell_measurement_theta_min      3.8290
_cell_volume                     2545.6(3)
_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    'SHELXS  (Sheldrick, 2008)'
_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 0.994
_diffrn_measured_fraction_theta_max 0.861
_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     66.00  92.00   1.00   50.00    --   22.36-144.00  41.00   26
  2  \w    -48.00  48.00   1.00   50.00    --   22.36 -23.00  65.00   96
  3  \w    -96.00 -39.00   1.00   50.00    --  -24.08-178.00 -90.00   57
  4  \w     33.00  59.00   1.00   50.00    --   21.89 -23.00  64.00   26
  5  \w     46.00  97.00   1.00   50.00    --   21.89 178.00  30.00   51
  6  \w    -90.00 -38.00   1.00   50.00    --  -23.61 -57.00-150.00   52
;
_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      -0.0047413000
_diffrn_orient_matrix_UB_12      -0.0520225000
_diffrn_orient_matrix_UB_13      -0.0216840000
_diffrn_orient_matrix_UB_21      -0.0393527000
_diffrn_orient_matrix_UB_22      0.0191323000
_diffrn_orient_matrix_UB_23      -0.0283920000
_diffrn_orient_matrix_UB_31      0.0294405000
_diffrn_orient_matrix_UB_32      0.0173172000
_diffrn_orient_matrix_UB_33      -0.0336971000
_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  0.0448
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16553
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.971
_diffrn_reflns_theta_min         3.620
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74008
_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    1.314
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         6968
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1294
_refine_ls_R_factor_gt           0.0605
_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^)+(0.1000P)^2^+0.0800P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1544
_refine_ls_wR_factor_ref         0.2183
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3480
_reflns_number_total             6968
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj02019j2.cif
_cod_data_source_block           exp_852
_cod_depositor_comments
'Adding full bibliography for 7061667--7061671.cif.'
_cod_database_code               7061667
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.958
_reflns_odcompleteness_completeness 99.47
_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:
 C6(H6), C9(H9), C8(H8), C7(H7), C21(H21), C19(H19), C18(H18), C17(H17),
 C27(H27), C20(H20), C33(H33), C32(H32), C31(H31), C26(H26), C29(H29), C23(H23),
  C24(H24), C30(H30), C25(H25)
;
_shelx_res_checksum              96657
_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 1.217
_oxdiff_exptl_absorpt_empirical_full_min 0.904