Unified synthesis of mono/bis-arylated phenols via Rh(III)-catalyzed dehydrogenative coupling.
Wu, Qian; Chen, Ying; Yan, Dingyuan; Zhang, Muyue; Lu, Yi; Sun, Wei-Yin; Zhao, Jing; Chemical science 8 (2017) 169–173; doi:10.1039/c6sc03169b

data_1543893
_publ_section_title
;
 Unified synthesis of mono/bis-arylated phenols via Rh(III)-catalyzed
 dehydrogenative coupling.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              169
_journal_page_last               173
_journal_paper_doi               10.1039/c6sc03169b
_journal_volume                  8
_journal_year                    2017
_chemical_formula_moiety         'C15 H12 N2 O2 S'
_chemical_formula_sum            'C15 H12 N2 O2 S'
_chemical_formula_weight         284.33
_chemical_name_common            chenying
_chemical_name_systematic        cy-P3-NHAc-thiazole
_chemical_properties_physical    'Hygroscopic, Heat-sensitive'
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-11-24 deposited with the CCDC.
2016-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.7941(7)
_cell_length_b                   15.333(2)
_cell_length_c                   17.698(3)
_cell_measurement_reflns_used    6071
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.565
_cell_measurement_theta_min      3.455
_cell_volume                     1300.9(3)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IP'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_av_unetI/netI     0.0909
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7897
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         3.516
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_size_max          0.186
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 524 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2850
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0567
_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^)+(0.0578P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1374
_reflns_Friedel_coverage         0.626
_reflns_Friedel_fraction_full    0.933
_reflns_Friedel_fraction_max     0.898
_reflns_number_gt                1950
_reflns_number_total             2850
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc03169b2.cif
_cod_data_source_block           A
_cod_depositor_comments
;
 Adding full bibliography for 1543891--1543894.cif.

2019-03-14
Z value and formula fixed from absurd original values
                 miguel
;
_cod_original_cell_volume        1301.0(3)
_cod_original_formula_sum        'C3.53 H2.82 N0.47 O0.47 S0.24'
_cod_original_formula_units_Z    17
_cod_original_formula_weight     66.90
_cod_database_code               1543893
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.955
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              27435