Phosphine-Free Ru-Catalyzed Regio- and Stereoselective Addition of Benzoic Acids to Trifluoromethylated Alkynes toward Facile Access to Trifluoromethyl Group-Substituted (E)-Enol Esters
Liu, Guangyuan; Zhang, Xingxing; Kuang, Guanghua; Lu, Naihao; Fu, Yang; Peng, Yiyuan; Xiao, Qiang; Zhou, Yirong; ACS Omega 5 (2020) 4158–4166; doi:10.1021/acsomega.9b03936

data_4517432
_publ_section_title
;
 Phosphine-Free Ru-Catalyzed Regio- and Stereoselective Addition of
 Benzoic Acids to Trifluoromethylated Alkynes toward Facile Access to
 Trifluoromethyl Group-Substituted (E)-Enol Esters
;
_journal_issue                   8
_journal_name_full               'ACS Omega'
_journal_page_first              4158
_journal_page_last               4166
_journal_paper_doi               10.1021/acsomega.9b03936
_journal_volume                  5
_journal_year                    2020
_chemical_formula_moiety         'C18 H14 F4 O4'
_chemical_formula_sum            'C18 H14 F4 O4'
_chemical_formula_weight         370.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.283(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7445(11)
_cell_length_b                   17.5810(12)
_cell_length_c                   7.2542(6)
_cell_measurement_reflns_used    5688
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.7830
_cell_measurement_theta_min      3.6920
_cell_volume                     1719.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0353
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.886
_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    -33.00  51.00   1.00    5.59    --  -15.92  57.00  30.00   84
  2  \w    -52.00  36.00   1.00    5.59    --   16.85 -37.00-180.00   88
  3  \w      0.00  84.00   1.00    5.59    --   16.85  57.00-180.00   84
  4  \w    -20.00  56.00   1.00    5.59    --   16.85 -99.00  60.00   76
  5  \w    -88.00 -61.00   1.00    5.59    --  -15.92-178.00  30.00   27
  6  \w     35.00  89.00   1.00    5.59    --   16.85 178.00  30.00   54
  7  \w    -10.00  84.00   1.00    5.59    --   16.85  77.00 -60.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0462745000
_diffrn_orient_matrix_UB_12      -0.0161760000
_diffrn_orient_matrix_UB_13      -0.0079554000
_diffrn_orient_matrix_UB_21      -0.0231459000
_diffrn_orient_matrix_UB_22      -0.0359530000
_diffrn_orient_matrix_UB_23      -0.0196606000
_diffrn_orient_matrix_UB_31      -0.0097980000
_diffrn_orient_matrix_UB_32      0.0085762000
_diffrn_orient_matrix_UB_33      -0.0974046000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.886
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            18798
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.465
_diffrn_reflns_theta_min         3.678
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.431
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_preparation       'as synthesized'
_exptl_crystal_recrystallization_method 'slow evaporation from a mixed solvent'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4225
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0571
_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^)+(0.0408P)^2^+0.6196P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1334
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2745
_reflns_number_total             4225
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao9b03936_si_001.cif
_cod_data_source_block           kgh20191009
_cod_depositor_comments
;Adding full bibliography for 4517432.cif.

 Adding full bibliography for 4517432.cif.
;
_cod_database_code               4517432
_shelxl_version_number           2014-1
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.927
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C7(H7), C3(H3), C4(H4), C12(H12), C17(H17), C13(H13), C16(H16), C15(H15)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              83558
_shelx_hkl_checksum              57727
_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 1.683
_oxdiff_exptl_absorpt_empirical_full_min 0.640