Selective Hydration of Asymmetric Internal Aryl Alkynes without Directing Groups to α-Aryl Ketones over Cu-based catalyst
Mei, Qingqing; Liu, Huizhen; Hou, Minqiang; Liu, Hangyu; Han, Buxing; New J. Chem. 41 (2017) 6290–6295; doi:10.1039/C7NJ00486A

data_7056251
_publ_section_title
;
 Selective Hydration of Asymmetric Internal Aryl Alkynes without Directing
 Groups to \a-Aryl Ketones over Cu-based catalyst
;
_journal_issue                   14
_journal_name_full               'New J. Chem.'
_journal_page_first              6290
_journal_page_last               6295
_journal_paper_doi               10.1039/C7NJ00486A
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety         'C14 H11 F O2'
_chemical_formula_sum            'C14 H11 F O2'
_chemical_formula_weight         230.23
_chemical_name_systematic
1-(4-hydroxyphenyl)ethan-2-(4-fluorophenyl)-1-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/cc1k95bc
_audit_creation_date             2015-09-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-11-25 deposited with the CCDC.
2017-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.287(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.940(2)
_cell_length_b                   16.998(5)
_cell_length_c                   8.091(2)
_cell_measurement_reflns_used    3919
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4801
_cell_measurement_theta_min      1.1980
_cell_volume                     1092.0(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 270.0000
                 XTD: 40.0380
              2theta: -19.9252
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 40.0380
              2theta: -19.9252
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0535
_diffrn_orient_matrix_UB_12      0.1041
_diffrn_orient_matrix_UB_13      -0.0466
_diffrn_orient_matrix_UB_21      -0.0531
_diffrn_orient_matrix_UB_22      -0.0210
_diffrn_orient_matrix_UB_23      0.0141
_diffrn_orient_matrix_UB_31      0.0079
_diffrn_orient_matrix_UB_32      0.0544
_diffrn_orient_matrix_UB_33      0.1107
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9507
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         2.788
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8292
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       rod
_exptl_crystal_F_000             480
_exptl_crystal_recrystallization_method 'Vapour Deposition'
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2501
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0458P)^2^+0.4451P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1178
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2401
_reflns_number_total             2501
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7nj00486a2.cif
_cod_data_source_block           mx4150
_cod_database_code               7056251
_shelxl_version_number           2013-4
_diffrn_number_total             2596
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C13(H13), C14(H14)
;
_shelx_res_checksum              27454
_olex2_submission_special_instructions 'No special instructions were received'