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_7061669
_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         'C27 H20 F3 N O5'
_chemical_formula_sum            'C27 H20 F3 N O5'
_chemical_formula_weight         495.44
_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     direct
_audit_creation_date             2020-09-22
_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                87.355(5)
_cell_angle_beta                 85.247(5)
_cell_angle_gamma                88.238(5)
_cell_formula_units_Z            4
_cell_length_a                   9.7920(6)
_cell_length_b                   12.2767(8)
_cell_length_c                   19.2845(12)
_cell_measurement_reflns_used    3470
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.7300
_cell_measurement_theta_min      3.6530
_cell_volume                     2307.0(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 0.992
_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    -10.00  63.00   1.00   60.00    --   22.21-101.00 161.00   73
  2  \w    -67.00  23.00   1.00   60.00    --  -23.92 101.00 -95.00   90
  3  \w      1.00  91.00   1.00   60.00    --   22.21  57.00 150.00   90
  4  \w     -2.00  92.00   1.00   60.00    --   22.21  38.00 -90.00   94
  5  \w    -92.00   4.00   1.00   60.00    --  -23.92 -77.00   0.00   96
;
_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      -0.0334647000
_diffrn_orient_matrix_UB_12      0.0194106000
_diffrn_orient_matrix_UB_13      -0.0295764000
_diffrn_orient_matrix_UB_21      0.0645052000
_diffrn_orient_matrix_UB_22      0.0061857000
_diffrn_orient_matrix_UB_23      -0.0191739000
_diffrn_orient_matrix_UB_31      -0.0025259000
_diffrn_orient_matrix_UB_32      -0.0541537000
_diffrn_orient_matrix_UB_33      -0.0110635000
_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  0.0522
_diffrn_reflns_av_unetI/netI     0.0946
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            22870
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.762
_diffrn_reflns_theta_min         3.526
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58475
_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    1.426
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     724
_refine_ls_number_reflns         12399
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1528
_refine_ls_R_factor_gt           0.0635
_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^)+(0.0670P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1968
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5586
_reflns_number_total             12399
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj02019j2.cif
_cod_data_source_block           exp_875
_cod_depositor_comments
'Adding full bibliography for 7061667--7061671.cif.'
_cod_database_code               7061669
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.947
_reflns_odcompleteness_completeness 98.93
_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. Restrained distances
 F1B-C1A
 1.34 with sigma of 0.02
 C1A-F3B
 1.34 with sigma of 0.02
 C1A-F3A
 1.34 with sigma of 0.02
 C1A-F1A
 1.34 with sigma of 0.02
 C1A-F2A
 1.34 with sigma of 0.02
 C1A-F2B
 1.34 with sigma of 0.02
3. Others
 Fixed Sof: F1A(0.7) F3A(0.7) F2A(0.7) F3B(0.3) F1B(0.3) F2B(0.3)
4.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C7(H7), C23(H23), C27(H27), C8(H8), C26(H26), C24(H24),
 C17(H17), C19(H19), C25(H25), C20(H20), C18(H18), C21(H21), C6A(H6A),
 C23A(H23A), C27A(H27A), C9A(H9A), C17A(H17A), C21A(H21A), C26A(H26A), C8A(H8A),
  C7A(H7A), C20A(H20A), C25A(H25A), C24A(H24A), C18A(H18A), C19A(H19A)
;
_shelx_res_checksum              67545
_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 1.292
_oxdiff_exptl_absorpt_empirical_full_min 0.771