Electrostatic Control of Regioselectivity in Au(I)-Catalyzed Hydroarylation.
Lau, Vivian M.; Pfalzgraff, William C.; Markland, Thomas E.; Kanan, Matthew W.; Journal of the American Chemical Society 139 (2017) 4035–4041; doi:10.1021/jacs.6b11971

data_4125857
_publ_section_title
;
 Electrostatic Control of Regioselectivity in Au(I)-Catalyzed
 Hydroarylation.
;
_journal_issue                   11
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4035
_journal_page_last               4041
_journal_paper_doi               10.1021/jacs.6b11971
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C19 H16 O2'
_chemical_formula_sum            'C19 H16 O2'
_chemical_formula_weight         276.32
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-01-29
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.923(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1333(6)
_cell_length_b                   9.4398(4)
_cell_length_c                   11.3277(5)
_cell_measurement_reflns_used    7258
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.462
_cell_measurement_theta_min      2.678
_cell_volume                     1374.06(11)
_computing_cell_refinement       'SAINT+ Ver. 8.34A (Bruker-AXS, 2014)'
_computing_data_collection       'APEX2 Ver. 2014.11-0 (Bruker-AXS, 2014)'
_computing_data_reduction        'SAINT+ Ver. 8.34A (Bruker-AXS, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon100'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17958
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_min         2.677
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0772 before and 0.0622 after correction. The Ratio of minimum to maximum transmission is 0.8805. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       needle
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0439
_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^+0.4755P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1098
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2316
_reflns_number_total             3154
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b11971_si_002.cif
_cod_data_source_block           p053
_cod_depositor_comments          'Adding full bibliography for 4125857.cif.'
_cod_database_code               4125857
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.986
_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:
 C4(H4), C5(H5), C7(H7), C15(H15), C16(H16), C3(H3), C10(H10), C11(H11),
 C12(H12), C2(H2)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              76646
_shelx_hkl_checksum              3667
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'