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#$Date: 2024-10-06 11:18:33 +0200 (Sun 06 de Oct de 2024) $
#$Revision: 295341 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/01/7160131.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7160131
loop_
_publ_author_name
'Gao, Zhiwei'
'Hou, Zhiguo'
'Gao, Hongyin'
_publ_section_title
;
 Regioselective synthesis of 2-aminophenols from
 N-arylhydroxylamines.
;
_journal_issue                   38
_journal_name_full               'Organic & 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 λ/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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.1003P)²] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.48941(6) 0.67022(4) 0.24988(6) 0.0649(5) Uani 1 1 d . . . . .
O1 O 0.3097(6) 0.7036(3) 0.4785(7) 0.0535(12) Uani 1 1 d . . . . .
O2 O 0.5955(7) 0.8949(3) 0.7114(8) 0.0575(13) Uani 1 1 d . . . . .
H2 H 0.684236 0.879915 0.791780 0.086 Uiso 1 1 calc R U . . .
C1 C 0.4485(7) 0.6954(4) 0.6105(9) 0.0412(13) Uani 1 1 d . . . . .
C4 C 0.4945(10) 0.6357(3) 0.7543(13) 0.0437(12) Uani 1 1 d . . . . .
N1 N 0.5645(6) 0.7402(3) 0.6286(8) 0.0455(12) Uani 1 1 d . . . . .
H1 H 0.658090 0.735528 0.727875 0.055 Uiso 1 1 calc R U . . .
C6 C 0.5395(8) 0.7949(4) 0.4912(12) 0.0467(17) Uani 1 1 d . . . . .
C8 C 0.6513(8) 0.6204(4) 0.8943(11) 0.0512(16) Uani 1 1 d . . . . .
H8 H 0.732370 0.650000 0.905145 0.061 Uiso 1 1 calc R U . . .
C10 C 0.3753(9) 0.5920(5) 0.7455(14) 0.0601(19) Uani 1 1 d . . . . .
H10 H 0.269872 0.602777 0.655723 0.072 Uiso 1 1 calc R U . . .
C12 C 0.4122(12) 0.5326(6) 0.8691(16) 0.072(2) Uani 1 1 d . . . . .
H12 H 0.332076 0.502933 0.860225 0.086 Uiso 1 1 calc R U . . .
C14 C 0.6863(11) 0.5611(5) 1.0174(13) 0.0626(19) Uani 1 1 d . . . . .
H14 H 0.791192 0.550428 1.109654 0.075 Uiso 1 1 calc R U . . .
C7 C 0.5673(14) 0.5179(5) 1.0043(14) 0.070(2) Uani 1 1 d . . . . .
H7 H 0.592156 0.478348 1.087907 0.084 Uiso 1 1 calc R U . . .
C2 C 0.5302(11) 0.9234(4) 0.4008(15) 0.061(2) Uani 1 1 d . . . . .
H2A H 0.541070 0.974141 0.430301 0.073 Uiso 1 1 calc R U . . .
C9 C 0.4880(13) 0.8999(4) 0.2208(15) 0.063(2) Uani 1 1 d . . . . .
H9 H 0.469198 0.936029 0.131088 0.075 Uiso 1 1 calc R U . . .
C5 C 0.4374(16) 0.8036(11) -0.0219(19) 0.084(3) Uani 1 1 d . . . . .
H5A H 0.401473 0.846330 -0.104177 0.126 Uiso 1 1 calc R U . . .
H5B H 0.356531 0.765850 -0.073739 0.126 Uiso 1 1 calc R U . . .
H5C H 0.531686 0.784002 -0.010256 0.126 Uiso 1 1 calc R U . . .
C11 C 0.5010(9) 0.7741(5) 0.3090(11) 0.0538(17) Uani 1 1 d . . . . .
C3 C 0.4727(11) 0.8263(5) 0.1694(15) 0.059(2) Uani 1 1 d . . . . .
C13 C 0.5563(8) 0.8697(5) 0.5368(12) 0.0512(17) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O2 H2 109.5 . . ?
O1 C1 C4 121.4(6) . . ?
O1 C1 N1 121.2(6) . . ?
N1 C1 C4 117.4(6) . . ?
C8 C4 C1 122.9(7) . . ?
C8 C4 C10 118.8(8) . . ?
C10 C4 C1 118.3(8) . . ?
C1 N1 H1 118.4 . . ?
C1 N1 C6 123.1(6) . . ?
C6 N1 H1 118.4 . . ?
C11 C6 N1 121.3(7) . . ?
C13 C6 N1 120.1(7) . . ?
C13 C6 C11 118.6(7) . . ?
C4 C8 H8 120.1 . . ?
C14 C8 C4 119.8(7) . . ?
C14 C8 H8 120.1 . . ?
C4 C10 H10 119.6 . . ?
C12 C10 C4 120.7(8) . . ?
C12 C10 H10 119.6 . . ?
C10 C12 H12 120.2 . . ?
C7 C12 C10 119.6(8) . . ?
C7 C12 H12 120.2 . . ?
C8 C14 H14 119.8 . . ?
C7 C14 C8 120.5(8) . . ?
C7 C14 H14 119.8 . . ?
C12 C7 C14 120.6(8) . . ?
C12 C7 H7 119.7 . . ?
C14 C7 H7 119.7 . . ?
C9 C2 H2A 120.5 . . ?
C9 C2 C13 119.1(8) . . ?
C13 C2 H2A 120.5 . . ?
C2 C9 H9 118.3 . . ?
C3 C9 C2 123.4(8) . . ?
C3 C9 H9 118.3 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
C6 C11 Br1 118.7(6) . . ?
C3 C11 Br1 118.4(6) . . ?
C3 C11 C6 122.9(8) . . ?
C9 C3 C5 121.4(11) . . ?
C9 C3 C11 116.1(9) . . ?
C11 C3 C5 122.4(10) . . ?
O2 C13 C6 122.5(7) . . ?
O2 C13 C2 117.6(8) . . ?
C6 C13 C2 119.9(8) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C11 1.909(9) . ?
O1 C1 1.235(8) . ?
O2 H2 0.8200 . ?
O2 C13 1.369(11) . ?
C1 C4 1.485(11) . ?
C1 N1 1.349(9) . ?
C4 C8 1.392(11) . ?
C4 C10 1.393(12) . ?
N1 H1 0.8600 . ?
N1 C6 1.425(9) . ?
C6 C11 1.407(13) . ?
C6 C13 1.376(14) . ?
C8 H8 0.9300 . ?
C8 C14 1.387(11) . ?
C10 H10 0.9300 . ?
C10 C12 1.386(13) . ?
C12 H12 0.9300 . ?
C12 C7 1.369(16) . ?
C14 H14 0.9300 . ?
C14 C7 1.372(15) . ?
C7 H7 0.9300 . ?
C2 H2A 0.9300 . ?
C2 C9 1.392(15) . ?
C2 C13 1.402(12) . ?
C9 H9 0.9300 . ?
C9 C3 1.366(12) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C5 C3 1.497(17) . ?
C11 C3 1.400(12) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C11 C3 C9 -177.7(7) . . . . ?
Br1 C11 C3 C5 -1.3(13) . . . . ?
O1 C1 C4 C8 173.8(7) . . . . ?
O1 C1 C4 C10 -4.7(12) . . . . ?
O1 C1 N1 C6 -5.6(11) . . . . ?
C1 C4 C8 C14 -176.4(8) . . . . ?
C1 C4 C10 C12 176.1(9) . . . . ?
C1 N1 C6 C11 -66.7(9) . . . . ?
C1 N1 C6 C13 114.8(8) . . . . ?
C4 C1 N1 C6 173.8(7) . . . . ?
C4 C8 C14 C7 -1.0(14) . . . . ?
C4 C10 C12 C7 1.6(17) . . . . ?
N1 C1 C4 C8 -5.6(11) . . . . ?
N1 C1 C4 C10 175.9(7) . . . . ?
N1 C6 C11 Br1 -2.1(9) . . . . ?
N1 C6 C11 C3 178.8(7) . . . . ?
N1 C6 C13 O2 -0.6(9) . . . . ?
N1 C6 C13 C2 -179.5(7) . . . . ?
C6 C11 C3 C9 1.4(13) . . . . ?
C6 C11 C3 C5 177.8(10) . . . . ?
C8 C4 C10 C12 -2.4(15) . . . . ?
C8 C14 C7 C12 0.2(16) . . . . ?
C10 C4 C8 C14 2.1(13) . . . . ?
C10 C12 C7 C14 -0.5(17) . . . . ?
C2 C9 C3 C5 -175.9(10) . . . . ?
C2 C9 C3 C11 0.5(15) . . . . ?
C9 C2 C13 O2 -179.1(7) . . . . ?
C9 C2 C13 C6 -0.2(11) . . . . ?
C11 C6 C13 O2 -179.2(7) . . . . ?
C11 C6 C13 C2 2.0(9) . . . . ?
C13 C6 C11 Br1 176.5(5) . . . . ?
C13 C6 C11 C3 -2.7(11) . . . . ?
C13 C2 C9 C3 -1.1(15) . . . . ?
