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#$Date: 2025-08-22 11:56:18 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301860 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/60/7126001.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_7126001
loop_
_publ_author_name
'Li, Xingjun'
'Wang, Jiang'
'Xie, Xiong'
'Dai, Wenhao'
'Han, Xu'
'Chen, Kaixian'
'Liu, Hong'
_publ_section_title
;
 Ir(iii)-Catalyzed direct C-H functionalization of N-phenylacetamide with
 α-diazo quinones: a novel strategy for producing
 2-hydroxy-2'-amino-1,2'-biaryl scaffolds.
;
_journal_issue                   23
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3441
_journal_page_last               3444
_journal_paper_doi               10.1039/c9cc08297b
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C18 H14 Br N O2'
_chemical_formula_sum            'C18 H14 Br N O2'
_chemical_formula_weight         356.21
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc248w4g
_audit_creation_date             2019-12-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-30 deposited with the CCDC.	2020-02-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.3242(3)
_cell_length_b                   12.6129(3)
_cell_length_c                   28.2407(8)
_cell_measurement_reflns_used    6203
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.055
_cell_measurement_theta_min      2.841
_cell_volume                     2965.06(15)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            32027
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.841
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.779
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0912 before and 0.0599 after correction. The Ratio of minimum to maximum transmission is 0.8035. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3030
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0354
_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/[σ²(Fo²)+(0.0274P)²+4.1331P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0689
_refine_ls_wR_factor_ref         0.0810
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2230
_reflns_number_total             3030
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc08297b2.cif
_cod_data_source_block           220191300_0m
_cod_depositor_comments
'Adding full bibliography for 7125998--7126001.cif.'
_cod_database_code               7126001
_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   0.808
_shelx_estimated_absorpt_t_min   0.665
_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(H1A), C16(H16), C13(H13), C15(H15), C9(H9), C10(H10), C5(H5), C2(H2),
 C4(H4), C3(H3)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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 0.31984(4) 0.89019(2) 0.21217(2) 0.03085(11) Uani 1 1 d . . . . .
O1 O 0.5266(3) 0.79763(15) 0.38150(7) 0.0248(5) Uani 1 1 d . . . . .
H1 H 0.545500 0.862820 0.379090 0.037 Uiso 1 1 calc GR . . . .
O2 O 0.9285(3) 0.50916(15) 0.36668(8) 0.0282(5) Uani 1 1 d . . . . .
N1 N 0.7446(3) 0.63309(18) 0.38759(8) 0.0208(5) Uani 1 1 d . . . . .
H1A H 0.727571 0.701427 0.391363 0.025 Uiso 1 1 calc R . . . .
C7 C 0.6143(3) 0.5629(2) 0.39750(10) 0.0201(6) Uani 1 1 d . . . . .
C16 C 0.3748(3) 0.6161(2) 0.29155(10) 0.0228(6) Uani 1 1 d . . . . .
H16 H 0.356089 0.542389 0.287414 0.027 Uiso 1 1 calc R . . . .
C14 C 0.3625(3) 0.7917(2) 0.26175(11) 0.0239(7) Uani 1 1 d . . . . .
C12 C 0.4646(3) 0.7605(2) 0.33941(10) 0.0215(6) Uani 1 1 d . . . . .
C17 C 0.8914(4) 0.6029(2) 0.37295(10) 0.0209(6) Uani 1 1 d . . . . .
C11 C 0.4421(3) 0.6509(2) 0.33418(10) 0.0198(6) Uani 1 1 d . . . . .
C6 C 0.6321(3) 0.4870(2) 0.43442(10) 0.0218(6) Uani 1 1 d . . . . .
C8 C 0.4729(3) 0.5725(2) 0.37264(10) 0.0207(6) Uani 1 1 d . . . . .
C13 C 0.4254(3) 0.8305(2) 0.30329(10) 0.0226(7) Uani 1 1 d . . . . .
H13 H 0.441896 0.904498 0.307244 0.027 Uiso 1 1 calc R . . . .
C15 C 0.3343(4) 0.6844(2) 0.25520(11) 0.0254(7) Uani 1 1 d . . . . .
H15 H 0.288656 0.658569 0.226606 0.030 Uiso 1 1 calc R . . . .
C9 C 0.3454(4) 0.5007(2) 0.38334(11) 0.0244(7) Uani 1 1 d . . . . .
H9 H 0.248043 0.505155 0.365915 0.029 Uiso 1 1 calc R . . . .
C1 C 0.5022(4) 0.4176(2) 0.44487(11) 0.0237(7) Uani 1 1 d . . . . .
C10 C 0.3598(4) 0.4263(2) 0.41778(11) 0.0258(7) Uani 1 1 d . . . . .
H10 H 0.272930 0.379378 0.423796 0.031 Uiso 1 1 calc R . . . .
C18 C 1.0113(4) 0.6901(2) 0.36545(11) 0.0284(7) Uani 1 1 d . . . . .
H18A H 1.097004 0.684241 0.389105 0.043 Uiso 1 1 calc GR . . . .
H18B H 0.957825 0.758894 0.368696 0.043 Uiso 1 1 calc GR . . . .
H18C H 1.057510 0.683983 0.333646 0.043 Uiso 1 1 calc GR . . . .
C5 C 0.7723(4) 0.4800(2) 0.46318(11) 0.0279(7) Uani 1 1 d . . . . .
H5 H 0.860342 0.526073 0.457344 0.034 Uiso 1 1 calc R . . . .
C2 C 0.5166(4) 0.3442(2) 0.48225(12) 0.0295(7) Uani 1 1 d . . . . .
H2 H 0.429888 0.297630 0.488959 0.035 Uiso 1 1 calc R . . . .
C4 C 0.7813(4) 0.4075(3) 0.49911(12) 0.0325(8) Uani 1 1 d . . . . .
H4 H 0.876232 0.403465 0.517708 0.039 Uiso 1 1 calc R . . . .
C3 C 0.6526(4) 0.3390(2) 0.50894(12) 0.0329(8) Uani 1 1 d . . . . .
H3 H 0.660423 0.289216 0.534086 0.039 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C12 O1 H1 109.5 . . ?
C7 N1 H1A 117.4 . . ?
C17 N1 H1A 117.4 . . ?
C17 N1 C7 125.1(2) . . ?
C6 C7 N1 118.8(3) . . ?
C8 C7 N1 119.7(3) . . ?
C8 C7 C6 121.5(3) . . ?
C11 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
C15 C16 C11 122.8(3) . . ?
C13 C14 Br1 117.8(2) . . ?
C13 C14 C15 121.7(3) . . ?
C15 C14 Br1 120.5(2) . . ?
O1 C12 C11 118.4(3) . . ?
O1 C12 C13 120.3(2) . . ?
C13 C12 C11 121.2(3) . . ?
O2 C17 N1 122.8(3) . . ?
O2 C17 C18 121.0(3) . . ?
N1 C17 C18 116.2(2) . . ?
C16 C11 C12 117.0(3) . . ?
C16 C11 C8 119.2(2) . . ?
C12 C11 C8 123.7(3) . . ?
C7 C6 C5 123.0(3) . . ?
C1 C6 C7 119.1(3) . . ?
C1 C6 C5 117.8(3) . . ?
C7 C8 C11 125.3(3) . . ?
C7 C8 C9 118.2(3) . . ?
C9 C8 C11 116.6(3) . . ?
C14 C13 C12 119.3(3) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C16 C15 C14 117.9(3) . . ?
C16 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.7(3) . . ?
C10 C9 H9 119.2 . . ?
C10 C1 C6 118.5(3) . . ?
C2 C1 C6 119.7(3) . . ?
C2 C1 C10 121.8(3) . . ?
C9 C10 C1 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C1 C10 H10 119.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(3) . . ?
C3 C2 H2 119.4 . . ?
C5 C4 H4 119.5 . . ?
C5 C4 C3 121.1(3) . . ?
C3 C4 H4 119.5 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
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 C14 1.905(3) . ?
O1 H1 0.8400 . ?
O1 C12 1.378(3) . ?
O2 C17 1.235(3) . ?
N1 H1A 0.8800 . ?
N1 C7 1.428(4) . ?
N1 C17 1.344(4) . ?
C7 C6 1.423(4) . ?
C7 C8 1.376(4) . ?
C16 H16 0.9500 . ?
C16 C11 1.399(4) . ?
C16 C15 1.381(4) . ?
C14 C13 1.375(4) . ?
C14 C15 1.386(4) . ?
C12 C11 1.402(4) . ?
C12 C13 1.388(4) . ?
C17 C18 1.500(4) . ?
C11 C8 1.492(4) . ?
C6 C1 1.422(4) . ?
C6 C5 1.424(4) . ?
C8 C9 1.427(4) . ?
C13 H13 0.9500 . ?
C15 H15 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.357(4) . ?
C1 C10 1.415(4) . ?
C1 C2 1.409(4) . ?
C10 H10 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C5 H5 0.9500 . ?
C5 C4 1.368(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.362(5) . ?
C4 H4 0.9500 . ?
C4 C3 1.404(5) . ?
C3 H3 0.9500 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168351733
