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_7061670
_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         'C31 H25 Cl F3 N O9, C7 H8'
_chemical_formula_sum            'C38 H33 Cl F3 N O9'
_chemical_formula_weight         740.13
_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_primary     iterative
_audit_creation_date             2021-05-12
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2022-02-24 deposited with the CCDC.	2022-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                73.898(8)
_cell_angle_beta                 86.642(8)
_cell_angle_gamma                83.762(8)
_cell_formula_units_Z            2
_cell_length_a                   8.9834(10)
_cell_length_b                   11.4504(11)
_cell_length_c                   19.4781(18)
_cell_measurement_reflns_used    2467
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      22.2150
_cell_measurement_theta_min      2.4240
_cell_volume                     1912.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_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
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9555
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9879
_diffrn_measured_fraction_theta_max 0.8398
_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    -39.00  43.00   1.00  100.00    --   17.44 -77.00 -30.00   82
  2  \w    -25.00  34.00   1.00  100.00    --   17.44 -57.00  60.00   59
  3  \w     -9.00  32.00   1.00  100.00    --   17.44  77.00  60.00   41
  4  \w     -7.00  39.00   1.00  100.00    --   17.44  77.00-180.00   46
  5  \w    -50.00  33.00   1.00  100.00    --   17.44 -57.00-150.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0312072000
_diffrn_orient_matrix_UB_12      -0.0325444000
_diffrn_orient_matrix_UB_13      -0.0208854000
_diffrn_orient_matrix_UB_21      -0.0050037000
_diffrn_orient_matrix_UB_22      -0.0505097000
_diffrn_orient_matrix_UB_23      0.0306026000
_diffrn_orient_matrix_UB_31      -0.0729064000
_diffrn_orient_matrix_UB_32      0.0241996000
_diffrn_orient_matrix_UB_33      0.0080703000
_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  0.0383
_diffrn_reflns_av_unetI/netI     0.1106
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13790
_diffrn_reflns_theta_full        26.000000
_diffrn_reflns_theta_max         29.12
_diffrn_reflns_theta_min         1.86
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.98a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.2850
_exptl_crystal_description       block
_exptl_crystal_F_000             768.8016
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.572067
_refine_diff_density_min         -0.685039
_refine_diff_density_rms         0.123057
_refine_ls_d_res_high            0.730259
_refine_ls_d_res_low             8.926233
_refine_ls_goodness_of_fit_ref   1.043143
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     491
_refine_ls_number_reflns         8637
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.040845
_refine_ls_R_factor_all          0.177662
_refine_ls_R_factor_gt           0.073808
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0843P)^2^+0.0222P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.225982
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                3589
_reflns_number_total             8637
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2nj02019j2.cif
_cod_data_source_block           exp_1204
_cod_depositor_comments
'Adding full bibliography for 7061667--7061671.cif.'
_cod_database_code               7061670
_reflns_odcompleteness_completeness 98.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.060
_oxdiff_exptl_absorpt_empirical_full_min 0.958