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#$Date: 2021-06-05 22:27:38 +0300 (Sat, 05 Jun 2021) $
#$Revision: 266160 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/80/7158019.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_7158019
loop_
_publ_author_name
'Zhuang, Shi-Yi'
'Tang, Yong-Xing'
'Chen, Xiang-Long'
'Wu, Yan-Dong'
'Wu, An-Xin'
_publ_section_title
;
 I₂-DMSO mediated oxidative amidation of methyl ketones with
 anthranils for the synthesis of α-ketoamides.
;
_journal_issue                   19
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4258
_journal_page_last               4262
_journal_paper_doi               10.1039/d1ob00468a
_journal_volume                  19
_journal_year                    2021
_chemical_formula_sum            'C15 H10 I N O3'
_chemical_formula_weight         379.14
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-08-30 deposited with the CCDC.	2021-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.7449(12)
_cell_length_b                   16.862(3)
_cell_length_c                   21.490(3)
_cell_measurement_reflns_used    4626
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      23.03
_cell_measurement_theta_min      2.60
_cell_volume                     2806.5(8)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            27931
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.659
_diffrn_reflns_theta_min         1.895
_exptl_absorpt_coefficient_mu    2.288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_description       Block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.809
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         4317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0594P)²+1.8952P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1349
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2430
_reflns_number_total             4317
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00468a2.cif
_cod_data_source_block           1_a
_cod_depositor_comments          'Adding full bibliography for 7158019.cif.'
_cod_original_cell_volume        2806.3(7)
_cod_database_code               7158019
_shelx_shelxl_version_number     2014/7
_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_min   0.633
_shelx_estimated_absorpt_t_max   0.684
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
C1 C 0.1055(5) 0.5855(2) 0.67895(16) 0.0557(9) Uani 1 1 d . . . . .
H1 H 0.1924 0.5708 0.7065 0.067 Uiso 1 1 calc R U . . .
C2 C -0.0325(5) 0.6303(2) 0.69946(18) 0.0617(9) Uani 1 1 d . . . . .
H2 H -0.0375 0.6463 0.7408 0.074 Uiso 1 1 calc R U . . .
C3 C -0.1630(6) 0.6515(3) 0.6591(2) 0.0707(11) Uani 1 1 d . . . . .
H3 H -0.2550 0.6821 0.6732 0.085 Uiso 1 1 calc R U . . .
C4 C -0.1571(6) 0.6273(3) 0.5980(2) 0.0750(11) Uani 1 1 d . . . . .
H4 H -0.2466 0.6404 0.5710 0.090 Uiso 1 1 calc R U . . .
C5 C -0.0194(5) 0.5841(2) 0.57689(17) 0.0627(10) Uani 1 1 d . . . . .
H5 H -0.0151 0.5691 0.5353 0.075 Uiso 1 1 calc R U . . .
C6 C 0.1138(5) 0.5623(2) 0.61658(15) 0.0509(8) Uani 1 1 d . . . . .
C7 C 0.2553(5) 0.5133(2) 0.58993(17) 0.0560(9) Uani 1 1 d . . . . .
C8 C 0.4205(5) 0.4932(2) 0.62668(16) 0.0560(8) Uani 1 1 d . . . . .
C9 C 0.6807(5) 0.41124(19) 0.61239(14) 0.0470(7) Uani 1 1 d . . . . .
C10 C 0.7654(5) 0.4315(2) 0.66700(15) 0.0542(9) Uani 1 1 d . . . . .
H10 H 0.7179 0.4694 0.6934 0.065 Uiso 1 1 calc R U . . .
C11 C 0.9197(5) 0.3957(2) 0.68229(16) 0.0565(9) Uani 1 1 d . . . . .
H11 H 0.9742 0.4091 0.7194 0.068 Uiso 1 1 calc R U . . .
C12 C 0.9946(5) 0.3402(2) 0.64353(17) 0.0523(8) Uani 1 1 d . . . . .
C13 C 0.9119(5) 0.3205(2) 0.58911(16) 0.0570(9) Uani 1 1 d . . . . .
H13 H 0.9621 0.2835 0.5626 0.068 Uiso 1 1 calc R U . . .
C14 C 0.7556(5) 0.3544(2) 0.57289(16) 0.0512(8) Uani 1 1 d . . . . .
C15 C 0.6764(7) 0.3270(3) 0.51473(19) 0.0730(11) Uani 1 1 d . . . . .
H15 H 0.7391 0.2903 0.4916 0.088 Uiso 1 1 calc R U . . .
I1 I 1.22842(4) 0.28482(2) 0.66641(2) 0.07336(15) Uani 1 1 d . . . . .
N1 N 0.5242(4) 0.44557(16) 0.59442(13) 0.0526(7) Uani 1 1 d . . . . .
H1A H 0.4902 0.4343 0.5574 0.063 Uiso 1 1 calc R U . . .
O1 O 0.2466(4) 0.4881(3) 0.53725(15) 0.0893(11) Uani 1 1 d . . . . .
O2 O 0.4492(5) 0.5181(3) 0.67824(14) 0.1035(13) Uani 1 1 d . . . . .
O3 O 0.5399(4) 0.3468(2) 0.49382(14) 0.0858(10) 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'
I I -0.4742 1.8119 '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
C2 C1 C6 119.6(4) . . ?
C2 C1 H1 120.2 . . ?
C6 C1 H1 120.2 . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 120.0(4) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 121.1(4) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 118.8(4) . . ?
C5 C6 C7 117.3(3) . . ?
C1 C6 C7 124.0(3) . . ?
O1 C7 C6 121.0(3) . . ?
O1 C7 C8 116.6(3) . . ?
C6 C7 C8 122.4(3) . . ?
O2 C8 N1 125.3(4) . . ?
O2 C8 C7 123.2(3) . . ?
N1 C8 C7 111.5(3) . . ?
C10 C9 N1 122.8(3) . . ?
C10 C9 C14 118.9(3) . . ?
N1 C9 C14 118.3(3) . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 121.2(3) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 118.8(4) . . ?
C13 C12 I1 119.6(3) . . ?
C11 C12 I1 121.6(3) . . ?
C12 C13 C14 121.5(3) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C9 119.4(3) . . ?
C13 C14 C15 116.7(3) . . ?
C9 C14 C15 123.9(4) . . ?
O3 C15 C14 127.0(4) . . ?
O3 C15 H15 116.5 . . ?
C14 C15 H15 116.5 . . ?
C8 N1 C9 129.0(3) . . ?
C8 N1 H1A 115.5 . . ?
C9 N1 H1A 115.5 . . ?
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 C2 1.382(5) . ?
C1 C6 1.397(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.379(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.487(5) . ?
C7 O1 1.211(4) . ?
C7 C8 1.542(5) . ?
C8 O2 1.205(4) . ?
C8 N1 1.331(4) . ?
C9 C10 1.387(5) . ?
C9 N1 1.398(5) . ?
C9 C14 1.405(5) . ?
C10 C11 1.379(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(5) . ?
C12 I1 2.096(4) . ?
C13 C14 1.383(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.467(5) . ?
C15 O3 1.197(5) . ?
C15 H15 0.9300 . ?
N1 H1A 0.8600 . ?
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
C6 C1 C2 C3 0.8(6) . . . . ?
C1 C2 C3 C4 0.6(7) . . . . ?
C2 C3 C4 C5 -1.7(7) . . . . ?
C3 C4 C5 C6 1.5(7) . . . . ?
C4 C5 C6 C1 -0.1(6) . . . . ?
C4 C5 C6 C7 178.2(4) . . . . ?
C2 C1 C6 C5 -1.0(5) . . . . ?
C2 C1 C6 C7 -179.2(4) . . . . ?
C5 C6 C7 O1 -6.1(6) . . . . ?
C1 C6 C7 O1 172.1(4) . . . . ?
C5 C6 C7 C8 172.8(3) . . . . ?
C1 C6 C7 C8 -9.0(6) . . . . ?
O1 C7 C8 O2 176.1(5) . . . . ?
C6 C7 C8 O2 -2.8(6) . . . . ?
O1 C7 C8 N1 -4.2(5) . . . . ?
C6 C7 C8 N1 176.9(3) . . . . ?
N1 C9 C10 C11 -179.9(3) . . . . ?
C14 C9 C10 C11 -0.6(5) . . . . ?
C9 C10 C11 C12 1.1(6) . . . . ?
C10 C11 C12 C13 -0.5(5) . . . . ?
C10 C11 C12 I1 -179.7(3) . . . . ?
C11 C12 C13 C14 -0.5(5) . . . . ?
I1 C12 C13 C14 178.6(3) . . . . ?
C12 C13 C14 C9 0.9(5) . . . . ?
C12 C13 C14 C15 -178.1(4) . . . . ?
C10 C9 C14 C13 -0.4(5) . . . . ?
N1 C9 C14 C13 179.0(3) . . . . ?
C10 C9 C14 C15 178.6(4) . . . . ?
N1 C9 C14 C15 -2.1(5) . . . . ?
C13 C14 C15 O3 177.2(5) . . . . ?
C9 C14 C15 O3 -1.8(7) . . . . ?
O2 C8 N1 C9 3.0(7) . . . . ?
C7 C8 N1 C9 -176.7(3) . . . . ?
C10 C9 N1 C8 -8.9(6) . . . . ?
C14 C9 N1 C8 171.8(4) . . . . ?
