Regio- and stereospecific <i>cis</i>-hydrophenoxylation of ynamides with acidic phenols.
Wang, Ting; Wan, Yuyan; Xu, Mingyao; Wang, Yi; Hong, Xu-Jia; Gao, Hui; Zhou, Zhi; Yi, Wei; Zeng, Zhongyi; Organic & biomolecular chemistry 21 (2023) 3073–3078; doi:10.1039/d3ob00082f

data_7159177
_publ_section_title
;
 Regio- and stereospecific <i>cis</i>-hydrophenoxylation of ynamides with
 acidic phenols.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3073
_journal_page_last               3078
_journal_paper_doi               10.1039/d3ob00082f
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C23 H20 N2 O3 S'
_chemical_formula_sum            'C23 H20 N2 O3 S'
_chemical_formula_weight         404.47
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-21
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-11-05 deposited with the CCDC.	2023-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                83.082(6)
_cell_angle_beta                 68.299(7)
_cell_angle_gamma                63.337(9)
_cell_formula_units_Z            2
_cell_length_a                   9.7863(9)
_cell_length_b                   10.1591(9)
_cell_length_c                   12.6200(8)
_cell_measurement_reflns_used    2998
_cell_measurement_temperature    249.97(10)
_cell_measurement_theta_max      28.7140
_cell_measurement_theta_min      2.2560
_cell_volume                     1040.23(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      249.97(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -54.00  34.00   1.00    1.20    --   12.05 -57.00 -30.00   88
  2  \w    -16.00  77.00   1.00    1.20    --   12.05  77.00-120.00   93
  3  \w    -16.00  85.00   1.00    1.20    --   12.05  57.00 120.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0523071000
_diffrn_orient_matrix_UB_12      -0.0354843000
_diffrn_orient_matrix_UB_13      -0.0548151000
_diffrn_orient_matrix_UB_21      -0.0486187000
_diffrn_orient_matrix_UB_22      0.0596572000
_diffrn_orient_matrix_UB_23      -0.0253501000
_diffrn_orient_matrix_UB_31      0.0493135000
_diffrn_orient_matrix_UB_32      0.0361120000
_diffrn_orient_matrix_UB_33      -0.0047934000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6733
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.247
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3659
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0428
_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^)+(0.0513P)^2^+0.1466P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1109
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2868
_reflns_number_total             3659
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00082f2.cif
_cod_data_source_block           ck
_cod_depositor_comments          'Adding full bibliography for 7159177.cif.'
_cod_original_cell_volume        1040.23(17)
_cod_database_code               7159177
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.975
_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
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12),
 C13(H13), C18(H18), C19(H19), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              74665
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.335
_oxdiff_exptl_absorpt_empirical_full_min 0.594