Ligand-Enabled, Copper-Promoted Regio- and Chemoselective Hydroxylation of Arenes, Aryl Halides, and Aryl Methyl Ethers.
Singh, Bijaya Kumar; Jana, Ranjan; The Journal of organic chemistry 81 (2016) 831–841; doi:10.1021/acs.joc.5b02302

data_4031900
_publ_section_title
;
 Ligand-Enabled, Copper-Promoted Regio- and Chemoselective Hydroxylation
 of Arenes, Aryl Halides, and Aryl Methyl Ethers.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              831
_journal_page_last               841
_journal_paper_doi               10.1021/acs.joc.5b02302
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C17 H14 N2 O2'
_chemical_formula_sum            'C17 H14 N2 O2'
_chemical_formula_weight         278.30
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2015-08-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.145(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1498(8)
_cell_length_b                   12.4223(14)
_cell_length_c                   15.9220(17)
_cell_measurement_reflns_used    5864
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.87
_cell_measurement_theta_min      2.61
_cell_volume                     1387.5(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16533
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.387
_diffrn_reflns_theta_min         2.095
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1147 before and 0.0585 after correction.
The Ratio of minimum to maximum transmission is 0.8741.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       needle
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0582P)^2^+0.2336P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1293
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2291
_reflns_number_total             3130
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02302_si_002.cif
_cod_data_source_block           rj_bs261_oct14_0m_a
_cod_database_code               4031900
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2A), C2(H2B), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13),
 C15(H15)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              53037
_shelx_hkl_checksum              39656
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'