Asymmetric catalytic [1,3]- or [3,3]-sigmatropic rearrangement of 3-allyloxy-4<i>H</i>-chromenones and their analogues.
Li, Yi; Ning, Lichao; Tang, Qi; Lan, Kexin; Yang, Bingqian; Lin, Qianchi; Feng, Xiaoming; Liu, Xiaohua; Chemical science 15 (2024) 11005–11012; doi:10.1039/d4sc02201g

data_1571942
_publ_section_title
;
 Asymmetric catalytic [1,3]- or [3,3]-sigmatropic rearrangement of
 3-allyloxy-4<i>H</i>-chromenones and their analogues.
;
_journal_issue                   28
_journal_name_full               'Chemical science'
_journal_page_first              11005
_journal_page_last               11012
_journal_paper_doi               10.1039/d4sc02201g
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H24 N2 O'
_chemical_formula_sum            'C31 H24 N2 O'
_chemical_formula_weight         440.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2022-08-31 deposited with the CCDC.	2024-06-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.1520(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.0335(2)
_cell_length_b                   6.21300(10)
_cell_length_c                   16.2341(3)
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.31
_cell_measurement_theta_min      2.88
_cell_volume                     1146.55(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13857
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.305
_diffrn_reflns_theta_min         2.881
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       rod
_exptl_crystal_F_000             464
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
_exptl_crystal_size_max          0.754
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.108
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
; 
 Flack x determined using 1643 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.15(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4041
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0316
_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^)+(0.0431P)^2^+0.1237P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0790
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                3903
_reflns_number_total             4041
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02201g1.cif
_cod_data_source_block           lii022
_cod_depositor_comments          'Adding full bibliography for 1571942.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1571942
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.659
_shelx_estimated_absorpt_t_max   0.938
_shelx_res_checksum              2032
_shelx_hkl_checksum              52129