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#$Date: 2024-02-16 04:33:29 +0200 (Fri, 16 Feb 2024) $
#$Revision: 289842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/81/7248179.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_7248179
loop_
_publ_author_name
'Zuo, Youpeng'
'Liu, Meijun'
'Du, Jun'
'Zhang, Tianren'
'Wang, Xiaoqing'
'Wang, Cong'
_publ_section_title
;
 Ir(iii)/Ag(i)-catalyzed directly C--H amidation of arenes with OH-free
 hydroxyamides as amidating agents
;
_journal_issue                   9
_journal_name_full               'RSC Advances'
_journal_page_first              5975
_journal_page_last               5980
_journal_paper_doi               10.1039/D4RA00517A
_journal_volume                  14
_journal_year                    2024
_chemical_formula_sum            'C20 H15 N3 O'
_chemical_formula_weight         313.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2023-12-18 deposited with the CCDC.	2024-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.728(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0992(4)
_cell_length_b                   20.6903(11)
_cell_length_c                   9.9276(6)
_cell_measurement_reflns_used    9659
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      2.95
_cell_volume                     1545.42(15)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0086
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            61845
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.625
_diffrn_reflns_theta_min         2.958
_exptl_absorpt_coefficient_mu    0.086
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3540
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0505
_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)+(0.0458P)²+0.6533P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1225
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3175
_reflns_number_total             3540
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra00517a2.cif
_cod_data_source_block           Mp
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7248179
_shelx_shelxl_version_number     2018/1
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 0.0949(2) 0.15222(7) 0.35325(16) 0.0431(3) Uani 1 1 d . . . . .
H1 H 0.009008 0.153495 0.259990 0.052 Uiso 1 1 calc R U . . .
C2 C 0.0908(2) 0.19705(9) 0.4560(2) 0.0556(4) Uani 1 1 d . . . . .
H2 H 0.000566 0.227728 0.431995 0.067 Uiso 1 1 calc R U . . .
C3 C 0.2200(3) 0.19625(9) 0.59351(19) 0.0579(4) Uani 1 1 d . . . . .
H3 H 0.217494 0.226542 0.661922 0.069 Uiso 1 1 calc R U . . .
C4 C 0.3525(2) 0.15062(8) 0.62921(16) 0.0528(4) Uani 1 1 d . . . . .
H4 H 0.440811 0.150749 0.721411 0.063 Uiso 1 1 calc R U . . .
C5 C 0.3558(2) 0.10441(7) 0.52924(15) 0.0410(3) Uani 1 1 d . . . . .
H5 H 0.443538 0.072762 0.555228 0.049 Uiso 1 1 calc R U . . .
C6 C 0.22690(17) 0.10559(6) 0.38960(14) 0.0338(3) Uani 1 1 d . . . . .
C7 C 0.23750(17) 0.05394(6) 0.28696(13) 0.0323(3) Uani 1 1 d . . . . .
C8 C 0.19882(16) 0.03888(6) 0.02829(13) 0.0307(3) Uani 1 1 d . . . . .
C9 C 0.28138(18) -0.02001(6) 0.04103(14) 0.0354(3) Uani 1 1 d . . . . .
H9 H 0.326717 -0.040009 0.131268 0.042 Uiso 1 1 calc R U . . .
C10 C 0.29905(17) -0.05100(6) -0.08012(14) 0.0340(3) Uani 1 1 d . . . . .
C11 C 0.3882(2) -0.11083(7) -0.06788(17) 0.0443(3) Uani 1 1 d . . . . .
H11 H 0.431841 -0.131808 0.021262 0.053 Uiso 1 1 calc R U . . .
C12 C 0.4113(2) -0.13820(8) -0.18464(18) 0.0475(4) Uani 1 1 d . . . . .
H12 H 0.471319 -0.177320 -0.174247 0.057 Uiso 1 1 calc R U . . .
C13 C 0.3450(2) -0.10762(8) -0.32040(18) 0.0482(4) Uani 1 1 d . . . . .
H13 H 0.361676 -0.126583 -0.399334 0.058 Uiso 1 1 calc R U . . .
C14 C 0.2562(2) -0.05038(7) -0.33757(16) 0.0440(3) Uani 1 1 d . . . . .
H14 H 0.211921 -0.030716 -0.428215 0.053 Uiso 1 1 calc R U . . .
C15 C 0.23116(17) -0.02068(6) -0.21783(14) 0.0344(3) Uani 1 1 d . . . . .
C16 C 0.14393(18) 0.03932(6) -0.22965(14) 0.0356(3) Uani 1 1 d . . . . .
H16 H 0.097305 0.059557 -0.319547 0.043 Uiso 1 1 calc R U . . .
C17 C 0.12644(16) 0.06835(6) -0.11198(13) 0.0317(3) Uani 1 1 d . . . . .
C18 C -0.1169(2) 0.14325(8) -0.24813(17) 0.0487(4) Uani 1 1 d . . . . .
H18 H -0.180106 0.116180 -0.324655 0.058 Uiso 1 1 calc R U . . .
C19 C -0.1562(2) 0.20609(8) -0.23119(19) 0.0556(4) Uani 1 1 d . . . . .
H19 H -0.249717 0.230617 -0.293158 0.067 Uiso 1 1 calc R U . . .
C20 C -0.0269(3) 0.22537(8) -0.10206(18) 0.0547(4) Uani 1 1 d . . . . .
H20 H -0.021403 0.266386 -0.062294 0.066 Uiso 1 1 calc R U . . .
N1 N 0.18506(15) 0.07320(5) 0.14613(11) 0.0351(3) Uani 1 1 d . . . . .
H1A H 0.137726 0.110952 0.126804 0.042 Uiso 1 1 calc R U . . .
N2 N 0.0888(2) 0.17852(6) -0.04126(14) 0.0509(3) Uani 1 1 d . . . . .
N3 N 0.03027(16) 0.12761(5) -0.13351(12) 0.0361(3) Uani 1 1 d . . . . .
O1 O 0.29182(15) -0.00008(5) 0.33024(11) 0.0448(3) 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 0.0033 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'
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
C6 C1 C2 120.01(14) . . ?
C3 C2 C1 120.24(15) . . ?
C4 C3 C2 119.86(15) . . ?
C3 C4 C5 120.65(15) . . ?
C4 C5 C6 119.65(14) . . ?
C1 C6 C5 119.55(13) . . ?
C1 C6 C7 123.49(12) . . ?
C5 C6 C7 116.94(12) . . ?
O1 C7 N1 124.38(12) . . ?
O1 C7 C6 121.14(11) . . ?
N1 C7 C6 114.47(11) . . ?
C9 C8 N1 123.83(11) . . ?
C9 C8 C17 118.53(11) . . ?
N1 C8 C17 117.62(11) . . ?
C8 C9 C10 121.50(12) . . ?
C11 C10 C9 122.13(12) . . ?
C11 C10 C15 118.25(12) . . ?
C9 C10 C15 119.58(12) . . ?
C12 C11 C10 121.09(14) . . ?
C11 C12 C13 120.32(14) . . ?
C14 C13 C12 120.57(14) . . ?
C13 C14 C15 120.28(14) . . ?
C16 C15 C10 118.23(12) . . ?
C16 C15 C14 122.28(12) . . ?
C10 C15 C14 119.47(13) . . ?
C17 C16 C15 121.50(12) . . ?
C16 C17 N3 118.26(11) . . ?
C16 C17 C8 120.63(12) . . ?
N3 C17 C8 121.09(11) . . ?
N3 C18 C19 107.38(14) . . ?
C18 C19 C20 105.00(14) . . ?
N2 C20 C19 112.10(14) . . ?
C7 N1 C8 127.96(11) . . ?
C20 N2 N3 104.36(13) . . ?
C18 N3 N2 111.17(12) . . ?
C18 N3 C17 126.63(12) . . ?
N2 N3 C17 122.01(11) . . ?
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
C1 C6 1.3851(19) . ?
C1 C2 1.388(2) . ?
C2 C3 1.379(3) . ?
C3 C4 1.373(3) . ?
C4 C5 1.386(2) . ?
C5 C6 1.3929(19) . ?
C6 C7 1.5009(18) . ?
C7 O1 1.2196(16) . ?
C7 N1 1.3617(16) . ?
C8 C9 1.3731(18) . ?
C8 N1 1.4076(16) . ?
C8 C17 1.4318(17) . ?
C9 C10 1.4162(18) . ?
C10 C11 1.4155(19) . ?
C10 C15 1.4173(18) . ?
C11 C12 1.364(2) . ?
C12 C13 1.403(2) . ?
C13 C14 1.363(2) . ?
C14 C15 1.4180(19) . ?
C15 C16 1.4115(19) . ?
C16 C17 1.3668(18) . ?
C17 N3 1.4256(16) . ?
C18 N3 1.3478(18) . ?
C18 C19 1.363(2) . ?
C19 C20 1.380(2) . ?
C20 N2 1.328(2) . ?
N2 N3 1.3608(16) . ?
