Asymmetric Synthesis of Chromanone Lactones via Vinylogous Conjugate Addition of Butenolide to 2-Ester Chromones
Li, Yi; Xin, Shuang; Weng, Rui; Liu, Xiaohua; Feng, Xiaoming; Chemical Science  (2022) –; doi:10.1039/D2SC02541H

data_1567230
_publ_section_title
;
 Asymmetric Synthesis of Chromanone Lactones via Vinylogous Conjugate
 Addition of Butenolide to 2-Ester Chromones
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC02541H
_journal_year                    2022
_chemical_absolute_configuration syn
_chemical_formula_sum            'C42 H74 Cl3 F0 N4 O8 S0 Sc'
_chemical_formula_weight         914.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc23q7gk
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-10-07 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2602(4)
_cell_length_b                   14.2440(5)
_cell_length_c                   25.4714(7)
_cell_measurement_reflns_used    9768
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.64
_cell_volume                     4811.0(3)
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            41155
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.306
_diffrn_reflns_theta_min         2.217
_exptl_absorpt_coefficient_mu    0.371
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1960
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.569
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 4532 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         11917
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.9209P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0913
_reflns_Friedel_coverage         0.817
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                10924
_reflns_number_total             11917
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc02541h2.cif
_cod_data_source_block           mo_20181208CFZ_ScPiPr2_0m_a
_cod_database_code               1567230
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              21079