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#$Date: 2024-12-06 22:37:42 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296689 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160244.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_7160244
loop_
_publ_author_name
'Chen, Xue'
'Fang, Shi-Jie'
'Zhou, Quan'
'Huang, Wei'
'Liu, Qiu-Lan'
'Wang, Lei'
_publ_section_title
;
 Cu(II)-catalyzed synthesis of N-sulfonated
 quinolin-2(1H)-one-3-carboxamides.
;
_journal_issue                   47
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9209
_journal_page_last               9213
_journal_paper_doi               10.1039/d4ob01071j
_journal_volume                  22
_journal_year                    2024
_chemical_formula_sum            'C17 H13 N2 O4 S'
_chemical_formula_weight         341.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2024-04-22 deposited with the CCDC.	2024-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.269(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.643(6)
_cell_length_b                   5.4637(13)
_cell_length_c                   28.909(6)
_cell_measurement_reflns_used    2032
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.11
_cell_measurement_theta_min      3.13
_cell_volume                     3173.5(14)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0349
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7564
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.749
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       block
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2792
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0622P)²+1.8581P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1304
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2005
_reflns_number_total             2792
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01071j2.cif
_cod_data_source_block           1_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7160243--7160244.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7160244
_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   0.943
_shelx_estimated_absorpt_t_max   0.964
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'
'-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
S1 S 0.25130(4) 1.01837(14) 0.13161(3) 0.0544(3) Uani 1 1 d . U . . .
O4 O 0.24678(8) 0.5168(3) 0.02902(6) 0.0454(5) Uani 1 1 d . . . . .
O3 O 0.12096(10) 1.0611(4) 0.05833(7) 0.0630(6) Uani 1 1 d . . . . .
O1 O 0.31354(9) 0.8992(5) 0.15025(8) 0.0756(7) Uani 1 1 d . U . . .
O2 O 0.25045(12) 1.2701(4) 0.11968(7) 0.0750(7) Uani 1 1 d . . . . .
N2 N 0.16573(9) 0.3690(4) -0.02988(7) 0.0386(5) Uani 1 1 d . . . . .
N1 N 0.21786(11) 0.8573(5) 0.08433(8) 0.0557(6) Uani 1 1 d . . . . .
H1 H 0.2408 0.7348 0.0783 0.067 Uiso 1 1 calc R U . . .
C10 C 0.18769(12) 0.5295(5) 0.00580(8) 0.0374(6) Uani 1 1 d . . . . .
C11 C 0.10112(11) 0.3606(5) -0.05763(8) 0.0373(6) Uani 1 1 d . . . . .
C16 C 0.05507(12) 0.5347(5) -0.04980(9) 0.0401(6) Uani 1 1 d . . . . .
C17 C 0.07730(13) 0.7089(5) -0.01298(9) 0.0436(7) Uani 1 1 d . . . . .
H17 H 0.0474 0.8267 -0.0075 0.052 Uiso 1 1 calc R U . . .
C9 C 0.13995(12) 0.7108(5) 0.01438(8) 0.0376(6) Uani 1 1 d . . . . .
C5 C 0.19943(12) 0.9764(5) 0.17137(8) 0.0427(6) Uani 1 1 d . . . . .
C12 C 0.08296(13) 0.1802(5) -0.09186(9) 0.0467(7) Uani 1 1 d . . . . .
H12 H 0.1139 0.0655 -0.0968 0.056 Uiso 1 1 calc R U . . .
C6 C 0.15346(14) 1.1520(5) 0.17550(10) 0.0520(7) Uani 1 1 d . . . . .
H6 H 0.1464 1.2861 0.1551 0.062 Uiso 1 1 calc R U . . .
C8 C 0.15781(14) 0.8948(5) 0.05330(9) 0.0467(7) Uani 1 1 d . . . . .
C4 C 0.20917(14) 0.7743(5) 0.20084(10) 0.0527(7) Uani 1 1 d . . . . .
H4 H 0.2396 0.6538 0.1975 0.063 Uiso 1 1 calc R U . . .
C15 C -0.01036(13) 0.5248(6) -0.07796(10) 0.0532(7) Uani 1 1 d . . . . .
H15 H -0.0416 0.6401 -0.0737 0.064 Uiso 1 1 calc R U . . .
C14 C -0.02790(13) 0.3466(6) -0.11143(10) 0.0578(8) Uani 1 1 d . . . . .
H14 H -0.0712 0.3403 -0.1298 0.069 Uiso 1 1 calc R U . . .
C13 C 0.01864(14) 0.1732(6) -0.11834(10) 0.0557(8) Uani 1 1 d . . . . .
H13 H 0.0059 0.0516 -0.1411 0.067 Uiso 1 1 calc R U . . .
C2 C 0.12809(15) 0.9309(7) 0.24102(10) 0.0612(9) Uani 1 1 d . . . . .
C7 C 0.11795(15) 1.1266(6) 0.21028(11) 0.0619(8) Uani 1 1 d . . . . .
H7 H 0.0865 1.2443 0.2130 0.074 Uiso 1 1 calc R U . . .
C3 C 0.17318(15) 0.7545(6) 0.23518(10) 0.0614(8) Uani 1 1 d . . . . .
H3 H 0.1794 0.6183 0.2550 0.074 Uiso 1 1 calc R U . . .
C1 C 0.09290(18) 0.9133(10) 0.28119(12) 0.1024(15) Uani 1 1 d . . . . .
H1A H 0.1247 0.9295 0.3110 0.154 Uiso 1 1 calc R U . . .
H1B H 0.0711 0.7575 0.2800 0.154 Uiso 1 1 calc R U . . .
H1C H 0.0605 1.0418 0.2782 0.154 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 '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
O2 S1 O1 119.56(15) . . ?
O2 S1 N1 109.79(14) . . ?
O1 S1 N1 103.87(13) . . ?
O2 S1 C5 108.09(13) . . ?
O1 S1 C5 108.89(13) . . ?
N1 S1 C5 105.81(12) . . ?
C10 N2 C11 124.8(2) . . ?
C8 N1 S1 127.7(2) . . ?
C8 N1 H1 116.2 . . ?
S1 N1 H1 116.2 . . ?
O4 C10 N2 119.2(2) . . ?
O4 C10 C9 124.0(2) . . ?
N2 C10 C9 116.7(2) . . ?
C12 C11 N2 120.1(2) . . ?
C12 C11 C16 121.1(2) . . ?
N2 C11 C16 118.8(2) . . ?
C11 C16 C15 118.5(2) . . ?
C11 C16 C17 117.5(2) . . ?
C15 C16 C17 124.0(2) . . ?
C9 C17 C16 122.9(2) . . ?
C9 C17 H17 118.5 . . ?
C16 C17 H17 118.5 . . ?
C17 C9 C10 119.2(2) . . ?
C17 C9 C8 119.0(2) . . ?
C10 C9 C8 121.8(2) . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 S1 120.2(2) . . ?
C4 C5 S1 118.9(2) . . ?
C13 C12 C11 119.1(2) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C5 C6 C7 119.1(3) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
O3 C8 N1 122.1(3) . . ?
O3 C8 C9 122.8(2) . . ?
N1 C8 C9 115.1(2) . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C14 C15 C16 120.1(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C12 C13 C14 120.7(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C7 C2 C3 118.2(3) . . ?
C7 C2 C1 121.2(4) . . ?
C3 C2 C1 120.6(3) . . ?
C2 C7 C6 121.4(3) . . ?
C2 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C4 C3 C2 121.7(3) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
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
S1 O2 1.417(2) . ?
S1 O1 1.431(2) . ?
S1 N1 1.639(2) . ?
S1 C5 1.756(3) . ?
O4 C10 1.252(3) . ?
O3 C8 1.215(3) . ?
N2 C10 1.350(3) . ?
N2 C11 1.391(3) . ?
N1 C8 1.368(3) . ?
N1 H1 0.8600 . ?
C10 C9 1.458(3) . ?
C11 C12 1.386(4) . ?
C11 C16 1.399(3) . ?
C16 C15 1.409(3) . ?
C16 C17 1.423(4) . ?
C17 C9 1.352(3) . ?
C17 H17 0.9300 . ?
C9 C8 1.491(4) . ?
C5 C6 1.374(4) . ?
C5 C4 1.381(4) . ?
C12 C13 1.372(4) . ?
C12 H12 0.9300 . ?
C6 C7 1.381(4) . ?
C6 H6 0.9300 . ?
C4 C3 1.374(4) . ?
C4 H4 0.9300 . ?
C15 C14 1.362(4) . ?
C15 H15 0.9300 . ?
C14 C13 1.396(4) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
C2 C7 1.375(5) . ?
C2 C3 1.377(5) . ?
C2 C1 1.508(4) . ?
C7 H7 0.9300 . ?
C3 H3 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O4 0.86 1.88 2.610(3) 141.3 .
N1 H1 O4 0.86 1.88 2.610(3) 141.3 .
N1 H1 O4 0.86 1.88 2.610(3) 141.3 .
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
O2 S1 N1 C8 -50.8(3) . . . . ?
O1 S1 N1 C8 -179.8(2) . . . . ?
C5 S1 N1 C8 65.6(3) . . . . ?
C11 N2 C10 O4 178.7(2) . . . . ?
C11 N2 C10 C9 -2.0(3) . . . . ?
C10 N2 C11 C12 -176.8(2) . . . . ?
C10 N2 C11 C16 2.3(4) . . . . ?
C12 C11 C16 C15 -0.7(4) . . . . ?
N2 C11 C16 C15 -179.8(2) . . . . ?
C12 C11 C16 C17 178.1(2) . . . . ?
N2 C11 C16 C17 -1.0(3) . . . . ?
C11 C16 C17 C9 -0.5(4) . . . . ?
C15 C16 C17 C9 178.3(2) . . . . ?
C16 C17 C9 C10 0.8(4) . . . . ?
C16 C17 C9 C8 -177.7(2) . . . . ?
O4 C10 C9 C17 179.7(2) . . . . ?
N2 C10 C9 C17 0.3(3) . . . . ?
O4 C10 C9 C8 -1.8(4) . . . . ?
N2 C10 C9 C8 178.8(2) . . . . ?
O2 S1 C5 C6 17.7(3) . . . . ?
O1 S1 C5 C6 149.0(2) . . . . ?
N1 S1 C5 C6 -99.9(2) . . . . ?
O2 S1 C5 C4 -157.4(2) . . . . ?
O1 S1 C5 C4 -26.1(3) . . . . ?
N1 S1 C5 C4 85.1(2) . . . . ?
N2 C11 C12 C13 179.0(2) . . . . ?
C16 C11 C12 C13 -0.1(4) . . . . ?
C4 C5 C6 C7 1.4(4) . . . . ?
S1 C5 C6 C7 -173.6(2) . . . . ?
S1 N1 C8 O3 -0.5(4) . . . . ?
S1 N1 C8 C9 -177.94(19) . . . . ?
C17 C9 C8 O3 -8.5(4) . . . . ?
C10 C9 C8 O3 173.0(3) . . . . ?
C17 C9 C8 N1 169.0(2) . . . . ?
C10 C9 C8 N1 -9.5(4) . . . . ?
C6 C5 C4 C3 -1.5(4) . . . . ?
S1 C5 C4 C3 173.5(2) . . . . ?
C11 C16 C15 C14 0.9(4) . . . . ?
C17 C16 C15 C14 -177.8(3) . . . . ?
C16 C15 C14 C13 -0.3(4) . . . . ?
C11 C12 C13 C14 0.7(4) . . . . ?
C15 C14 C13 C12 -0.5(5) . . . . ?
C3 C2 C7 C6 -2.3(4) . . . . ?
C1 C2 C7 C6 175.5(3) . . . . ?
C5 C6 C7 C2 0.6(4) . . . . ?
C5 C4 C3 C2 -0.3(4) . . . . ?
C7 C2 C3 C4 2.2(4) . . . . ?
C1 C2 C3 C4 -175.6(3) . . . . ?
