Enantioselective synthesis of chiral 3-alkyl-3-nitro-4-chromanones via chiral thiourea-catalysed intramolecular Michael-type cyclization.
Chen, Huiqing; Tang, Jie; Liu, Ting; Yu, Li-Fang; Xing, Dong; Yang, Fan; Organic & biomolecular chemistry 19 (2021) 7403–7408; doi:10.1039/d1ob01296g

data_7158239
_publ_section_title
;
 Enantioselective synthesis of chiral 3-alkyl-3-nitro-4-chromanones via
 chiral thiourea-catalysed intramolecular Michael-type cyclization.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7403
_journal_page_last               7408
_journal_paper_doi               10.1039/d1ob01296g
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H17 F N2 O5'
_chemical_formula_weight         372.34
_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_Hall           'P 4w'
_space_group_name_H-M_alt        'P 41'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2021-07-02 deposited with the CCDC.	2021-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5302(3)
_cell_length_b                   9.5302(3)
_cell_length_c                   19.3236(5)
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      140.093
_cell_measurement_theta_min      9.380
_cell_volume                     1755.06(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16115
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.489
_diffrn_reflns_theta_min         4.640
_exptl_absorpt_coefficient_mu    0.931
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.090
_refine_diff_density_min         -0.098
_refine_diff_density_rms         0.020
_refine_ls_abs_structure_details
; 
 Flack x determined using 1385 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.03(7)
_refine_ls_extinction_coef       0.021(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3121
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0290
_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^)+(0.0335P)^2^+0.1536P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0726
_reflns_Friedel_coverage         0.930
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                2995
_reflns_number_total             3121
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01296g2.cif
_cod_data_source_block           cu_d8v19901_0m
_cod_depositor_comments          'Adding full bibliography for 7158239.cif.'
_cod_original_cell_volume        1755.06(12)
_cod_database_code               7158239
_shelx_estimated_absorpt_t_min   0.836
_shelx_estimated_absorpt_t_max   0.881
_shelxl_version_number           2013-4
_shelx_res_checksum              68665
_shelx_hkl_checksum              54669