Chiral Brønsted acid-catalyzed intermolecular hydrophenoxylation of ynamides with biaryl phenols <i>via</i> sequential desymmetrization/kinetic resolution.
Yu, Yu; Chen, Min; Organic & biomolecular chemistry 23 (2025) 5318–5322; doi:10.1039/d5ob00503e

data_7160531
_publ_section_title
;
 Chiral Br&#xf8;nsted acid-catalyzed intermolecular hydrophenoxylation of
 ynamides with biaryl phenols <i>via</i> sequential
 desymmetrization/kinetic resolution.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5318
_journal_page_last               5322
_journal_paper_doi               10.1039/d5ob00503e
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C32 H26 Br N O5 S'
_chemical_formula_sum            'C32 H26 Br N O5 S'
_chemical_formula_weight         616.51
_chemical_name_systematic        yy-1
_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   geom
_audit_creation_date             2025-01-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-01-20 deposited with the CCDC.	2025-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3191(6)
_cell_length_b                   21.290(2)
_cell_length_c                   21.290(2)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.28
_cell_measurement_theta_min      2.55
_cell_volume                     2864.2(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0819
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            161499
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         65.585
_diffrn_reflns_theta_min         2.554
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.963
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 - Bruker AXS'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_preparation       'slow evaporation in DCM'
_exptl_crystal_recrystallization_method 'by slow evaporation in DCM'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 2816 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.026(7)
_refine_ls_extinction_coef       0.00163(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         7491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0322P)^2^+1.2710P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0734
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                6888
_reflns_number_total             7491
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00503e2.cif
_cod_data_source_block           t
_cod_depositor_comments          'Adding full bibliography for 7160531.cif.'
_cod_original_cell_volume        2864.1(5)
_cod_database_code               7160531
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.828
_shelx_estimated_absorpt_t_min   0.650
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C13(H13), C14(H14), C15(H15), C17(H17), C19(H19), C20(H20),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28), C29(H29),
  C30(H30), C31(H31), C32(H32)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_olex2_submission_original_sample_id T
_olex2_submission_special_instructions 'No special instructions were received'