Regioselective synthesis of 2-aminophenols from <i>N</i>-arylhydroxylamines.
Gao, Zhiwei; Hou, Zhiguo; Gao, Hongyin; Organic & biomolecular chemistry 22 (2024) 7801–7805; doi:10.1039/d4ob01281j

data_7160131
_publ_section_title
;
 Regioselective synthesis of 2-aminophenols from
 <i>N</i>-arylhydroxylamines.
;
_journal_issue                   38
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7801
_journal_page_last               7805
_journal_paper_doi               10.1039/d4ob01281j
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C14 H12 Br N O2'
_chemical_formula_sum            'C14 H12 Br N O2'
_chemical_formula_weight         306.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-11-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-11-29 deposited with the CCDC.	2024-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 122.348(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9951(10)
_cell_length_b                   17.872(2)
_cell_length_c                   8.3591(9)
_cell_measurement_reflns_used    4292
_cell_measurement_temperature    298
_cell_measurement_theta_max      68.755
_cell_measurement_theta_min      4.949
_cell_volume                     1261.5(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8VENTURE PHOTON III'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0892
_diffrn_reflns_av_unetI/netI     0.0792
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5234
_diffrn_reflns_point_group_measured_fraction_full 0.633
_diffrn_reflns_point_group_measured_fraction_max 0.633
_diffrn_reflns_theta_full        66.493
_diffrn_reflns_theta_max         66.493
_diffrn_reflns_theta_min         4.949
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    4.391
_exptl_absorpt_correction_T_max  0.1665
_exptl_absorpt_correction_T_min  0.0467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1431 before and 0.0791 after correction.
The Ratio of minimum to maximum transmission is 0.2805.
The \l/2 correction factor is Not present.
;
_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    1.612
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.957
_refine_diff_density_min         -0.887
_refine_diff_density_rms         0.314
_refine_ls_abs_structure_details
;
 Flack x determined using 269 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(4)
_refine_ls_extinction_coef       0.0106(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1409
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.174
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0656
_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^)+(0.1003P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1415
_reflns_Friedel_coverage         0.268
_reflns_Friedel_fraction_full    0.269
_reflns_Friedel_fraction_max     0.269
_reflns_number_gt                1385
_reflns_number_total             1409
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01281j2.cif
_cod_data_source_block           cu_231107a_0m
_cod_depositor_comments          'Adding full bibliography for 7160131.cif.'
_cod_database_code               7160131
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.621
_shelx_estimated_absorpt_t_min   0.505
_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:
 N1(H1), C8(H8), C10(H10), C12(H12), C14(H14), C7(H7), C2(H2A), C9(H9)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              80519
_olex2_submission_special_instructions 'No special instructions were received'