Organocatalytic atroposelective fluorooxindole addition to coumarin Michael acceptors
Bouda, Maria; Hana, Grace E.; Xhili, Dea; Sripada, Archita; Bertke, Jeffery A.; Wolf, Christian; Chemical Communications 61 (2025) 7883–7886; doi:10.1039/D5CC01166C

data_7134477
_publ_section_title
;
 Organocatalytic atroposelective fluorooxindole addition to coumarin
 Michael acceptors
;
_journal_issue                   43
_journal_name_full               'Chemical Communications'
_journal_page_first              7883
_journal_page_last               7886
_journal_paper_doi               10.1039/D5CC01166C
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H10 Cl F N2 O5'
_chemical_formula_sum            'C18 H10 Cl F N2 O5'
_chemical_formula_weight         388.73
_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     intrinsic
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2025-02-21 deposited with the CCDC.	2025-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.6830(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7610(2)
_cell_length_b                   10.0249(2)
_cell_length_c                   17.7207(4)
_cell_measurement_reflns_used    9289
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.46
_cell_measurement_theta_min      2.78
_cell_volume                     1677.40(6)
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_collection       'APEX4 V2016.5-0 (Bruker, 2016)'
_computing_data_reduction
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_molecular_graphics    'SHELXLE v932 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Quest/Photon 3'
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            73034
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.536
_diffrn_reflns_theta_min         2.714
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  0.98870
_exptl_absorpt_correction_T_min  0.95979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.314
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.107
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 4459 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.018(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         10217
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0521P)^2^+0.3044P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0863
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                9793
_reflns_number_total             10217
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01166c2.cif
_cod_data_source_block           B25039_a
_cod_depositor_comments
'Adding full bibliography for 7134475--7134477.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7134477
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.919
_shelx_estimated_absorpt_t_max   0.971
_shelx_res_checksum              57413
_shelx_hkl_checksum              15060