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_7061668
_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 H23 F3 O3'
_chemical_formula_sum            'C33 H23 F3 O3'
_chemical_formula_weight         524.51
_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   geom
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_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-03-02
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  Olex2 1.2-ac2
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_audit_update_record
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2022-02-24 deposited with the CCDC.	2022-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                95.452(6)
_cell_angle_beta                 94.131(5)
_cell_angle_gamma                97.412(5)
_cell_formula_units_Z            4
_cell_length_a                   11.9059(6)
_cell_length_b                   13.1467(9)
_cell_length_c                   16.8474(12)
_cell_measurement_reflns_used    2614
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.8180
_cell_measurement_theta_min      2.0930
_cell_volume                     2593.6(3)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9872
_diffrn_measured_fraction_theta_max 0.9346
_diffrn_measurement_details
;
  1 omega  -97.00  -48.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6362 -178.0000   30.0000 49

  2 omega  -22.00   21.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6362  -99.0000  -90.0000 43

  3 omega   35.00   99.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1362  178.0000  -60.0000 64

  4 omega    2.00   91.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1362   57.0000   60.0000 89

  5 omega  -10.00   86.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1362   19.0000    0.0000 96
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0011451000
_diffrn_orient_matrix_UB_12      0.0358241000
_diffrn_orient_matrix_UB_13      0.0340828000
_diffrn_orient_matrix_UB_21      -0.0194978000
_diffrn_orient_matrix_UB_22      -0.0410011000
_diffrn_orient_matrix_UB_23      0.0222165000
_diffrn_orient_matrix_UB_31      0.0570468000
_diffrn_orient_matrix_UB_32      -0.0053822000
_diffrn_orient_matrix_UB_33      0.0121082000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0842
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            20412
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.57
_diffrn_reflns_theta_min         1.57
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
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_refine_ls_number_parameters     767
_refine_ls_number_reflns         13600
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1758
_refine_ls_R_factor_gt           0.0659
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0792P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.2033
_reflns_number_gt                5830
_reflns_number_total             13600
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2nj02019j2.cif
_cod_data_source_block           exp_1137
_cod_depositor_comments
'Adding full bibliography for 7061667--7061671.cif.'
_cod_database_code               7061668
_reflns_odcompleteness_completeness 98.72
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_reflns_odcompleteness_theta     28.22