#------------------------------------------------------------------------------
#$Date: 2020-08-06 16:44:01 +0200 (Thu 06 de Aug de 2020) $
#$Revision: 255095 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/75/7157547.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_7157547
loop_
_publ_author_name
'Tikhonova, Tatyana A.'
'Ilment, Nikita V.'
'Lyssenko, Konstantin A.'
'Zavarzin, Igor V.'
'Volkova, Yulia A.'
_publ_section_title
;
 Sulfur-mediated synthesis of unsymmetrically substituted N-aryl
 oxalamides by the cascade thioamidation/cyclocondensation and hydrolysis
 reaction.
;
_journal_issue                   26
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5050
_journal_page_last               5060
_journal_paper_doi               10.1039/d0ob00811g
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C20 H16 Cl N3 O2 , S O C2 H6'
_chemical_formula_sum            'C22 H19 Cl N3 O3 S'
_chemical_formula_weight         440.91
_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   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-07-21 deposited with the CCDC.	2020-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.604(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   35.957(3)
_cell_length_b                   6.1171(5)
_cell_length_c                   19.5083(15)
_cell_measurement_reflns_used    2360
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.2
_cell_volume                     4262.4(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector''
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            24783
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.996
_diffrn_reflns_theta_min         2.102
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.747
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       block
_exptl_crystal_F_000             1832
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.140
_exptl_transmission_factor_max   0.958
_exptl_transmission_factor_min   0.880
_refine_diff_density_max         1.034
_refine_diff_density_min         -0.807
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         5675
_refine_ls_number_restraints     138
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0668
_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)+(0.1140P)²+7.3396P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1951
_refine_ls_wR_factor_ref         0.2045
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4770
_reflns_number_total             5675
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            d0ob00811g2.cif
_cod_data_source_block           a_a_sq
_cod_depositor_comments
'Adding full bibliography for 7157546--7157547.cif.'
_cod_original_cell_volume        4262.5(6)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7157547
_shelx_shelxl_version_number     2016/6
_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   0.880
_shelx_estimated_absorpt_t_max   0.958
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
C1 C 0.3427(2) -0.6204(18) 0.6653(7) 0.0357(14) Uani 0.479(3) 1 d G U P A 1
H1A H 0.343769 -0.748407 0.693056 0.043 Uiso 0.479(3) 1 calc R U P A 1
C2 C 0.37489(18) -0.4988(19) 0.6603(5) 0.0359(13) Uani 0.479(3) 1 d G U P A 1
H2A H 0.398038 -0.543725 0.684677 0.043 Uiso 0.479(3) 1 calc R U P A 1
C3 C 0.3733(3) -0.3116(19) 0.6198(6) 0.0258(13) Uani 0.479(3) 1 d G U P A 1
C4 C 0.3394(4) -0.246(3) 0.5841(8) 0.0222(10) Uani 0.479(3) 1 d G U P A 1
C5 C 0.3072(3) -0.367(3) 0.5891(9) 0.0257(7) Uani 0.479(3) 1 d G U P A 1
H5A H 0.284026 -0.322542 0.564779 0.031 Uiso 0.479(3) 1 calc R U P A 1
C6 C 0.3088(2) -0.555(3) 0.6297(9) 0.0298(9) Uani 0.479(3) 1 d G . P A 1
H6A H 0.286762 -0.637813 0.633106 0.036 Uiso 0.479(3) 1 calc R U P A 1
C7 C 0.40840(14) -0.1796(9) 0.6168(3) 0.0420(11) Uani 0.479(3) 1 d G U P A 1
C8 C 0.42651(16) -0.1950(10) 0.5578(3) 0.0545(12) Uani 0.479(3) 1 d G U P A 1
H8A H 0.417635 -0.294187 0.522121 0.065 Uiso 0.479(3) 1 calc R U P A 1
C9 C 0.45760(14) -0.0653(10) 0.5509(2) 0.0740(15) Uani 0.479(3) 1 d G U P A 1
H9A H 0.469977 -0.075806 0.510534 0.089 Uiso 0.479(3) 1 calc R U P A 1
C10 C 0.47059(11) 0.0798(9) 0.6031(3) 0.0685(16) Uani 0.479(3) 1 d G U P A 1
H10A H 0.491837 0.168461 0.598349 0.082 Uiso 0.479(3) 1 calc R U P A 1
C11 C 0.45248(11) 0.0952(7) 0.6621(3) 0.0642(13) Uani 0.479(3) 1 d G U P A 1
H11A H 0.461356 0.194349 0.697751 0.077 Uiso 0.479(3) 1 calc R U P A 1
C12 C 0.42139(11) -0.0345(8) 0.6690(2) 0.0448(10) Uani 0.479(3) 1 d G U P A 1
N13 N 0.40821(17) -0.0337(13) 0.7282(3) 0.0720(13) Uani 0.479(3) 1 d . . P A 1
H13D H 0.418931 0.047075 0.762243 0.086 Uiso 0.479(3) 1 calc R U P A 1
H13E H 0.388548 -0.113979 0.734367 0.086 Uiso 0.479(3) 1 calc R U P A 1
C14 C 0.32673(5) 0.2515(3) 0.47383(10) 0.0241(4) Uani 1 1 d . . . . .
N15 N 0.29991(4) 0.3735(3) 0.43902(8) 0.0235(3) Uani 1 1 d . . . . .
H15A H 0.276617 0.334159 0.442075 0.028 Uiso 1 1 calc R U . . .
C16 C 0.31070(5) 0.0623(3) 0.51402(9) 0.0216(3) Uani 1 1 d . . . . .
O17 O 0.27703(4) 0.0356(2) 0.51417(8) 0.0290(3) Uani 1 1 d . . . . .
N18 N 0.33866(4) -0.0576(3) 0.54635(9) 0.0251(3) Uani 1 1 d . . . . .
H18N H 0.358661 -0.008814 0.540282 0.035(7) Uiso 1 1 d R . . A .
C19 C 0.30515(5) 0.5588(3) 0.39795(9) 0.0224(4) Uani 1 1 d . . . . .
C20 C 0.33954(6) 0.6602(4) 0.39705(13) 0.0367(5) Uani 1 1 d . . . . .
H20A H 0.360984 0.603168 0.424181 0.044 Uiso 1 1 calc R U . . .
C21 C 0.34288(6) 0.8450(4) 0.35666(13) 0.0366(5) Uani 1 1 d . . . . .
H21A H 0.366473 0.914784 0.356525 0.044 Uiso 1 1 calc R U . . .
C22 C 0.31190(6) 0.9264(3) 0.31693(10) 0.0267(4) Uani 1 1 d . . . . .
C23 C 0.27729(6) 0.8262(4) 0.31646(11) 0.0300(4) Uani 1 1 d . . . . .
H23A H 0.256022 0.882823 0.288731 0.036 Uiso 1 1 calc R U . . .
C24 C 0.27405(5) 0.6419(3) 0.35700(10) 0.0266(4) Uani 1 1 d . . . . .
H24A H 0.250449 0.571978 0.356784 0.032 Uiso 1 1 calc R U . . .
Cl25 Cl 0.31642(2) 1.15875(9) 0.26696(3) 0.03571(16) Uani 1 1 d . . . . .
O26 O 0.36063(4) 0.2761(3) 0.47596(9) 0.0381(4) Uani 1 1 d . . . . .
C1' C 0.3323(2) -0.6259(16) 0.6679(6) 0.0357(14) Uani 0.521(3) 1 d G U P A 2
H1'A H 0.331423 -0.754578 0.694930 0.043 Uiso 0.521(3) 1 calc R U P A 2
C2' C 0.36527(17) -0.5056(17) 0.6708(4) 0.0359(13) Uani 0.521(3) 1 d G U P A 2
H2'A H 0.386870 -0.552053 0.699734 0.043 Uiso 0.521(3) 1 calc R U P A 2
C3' C 0.3666(2) -0.3173(17) 0.6312(5) 0.0258(13) Uani 0.521(3) 1 d G U P A 2
C4' C 0.3350(3) -0.249(2) 0.5888(7) 0.0222(10) Uani 0.521(3) 1 d G U P A 2
C5' C 0.3021(3) -0.370(3) 0.5860(8) 0.0257(7) Uani 0.521(3) 1 d G U P A 2
H5'A H 0.280461 -0.323224 0.556995 0.031 Uiso 0.521(3) 1 calc R U P A 2
C6' C 0.3007(2) -0.558(2) 0.6255(8) 0.0298(9) Uani 0.521(3) 1 d G U P A 2
H6'A H 0.278218 -0.640162 0.623559 0.036 Uiso 0.521(3) 1 calc R U P A 2
C7' C 0.40279(12) -0.1853(9) 0.6349(2) 0.0420(11) Uani 0.521(3) 1 d G U P A 2
C8' C 0.41241(12) -0.0708(9) 0.6960(2) 0.0545(12) Uani 0.521(3) 1 d G U P A 2
H8'A H 0.396935 -0.079393 0.732181 0.065 Uiso 0.521(3) 1 calc R U P A 2
C9' C 0.44468(13) 0.0561(9) 0.7040(2) 0.0740(15) Uani 0.521(3) 1 d G U P A 2
H9'A H 0.451256 0.134335 0.745661 0.089 Uiso 0.521(3) 1 calc R U P A 2
C10' C 0.46733(10) 0.0686(8) 0.6509(3) 0.0685(16) Uani 0.521(3) 1 d G U P A 2
H10B H 0.489380 0.155390 0.656419 0.082 Uiso 0.521(3) 1 calc R U P A 2
C11' C 0.45770(10) -0.0458(8) 0.5899(2) 0.0642(13) Uani 0.521(3) 1 d G U P A 2
H11B H 0.473181 -0.037280 0.553697 0.077 Uiso 0.521(3) 1 calc R U P A 2
C12' C 0.42544(12) -0.1728(8) 0.5819(2) 0.0448(10) Uani 0.521(3) 1 d G U P A 2
N13' N 0.41522(15) -0.3009(12) 0.5202(3) 0.0720(13) Uani 0.521(3) 1 d . . P A 2
H13A H 0.429585 -0.299675 0.486634 0.086 Uiso 0.521(3) 1 calc R U P A 2
H13C H 0.394650 -0.380063 0.516343 0.086 Uiso 0.521(3) 1 calc R U P A 2
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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 120.0 . . ?
C2 C1 H1A 120.0 . . ?
C6 C1 H1A 120.0 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 C7 121.1(8) . . ?
C2 C3 C7 118.9(8) . . ?
N18 C4 C5 121.6(9) . . ?
N18 C4 C3 118.4(9) . . ?
C5 C4 C3 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6A 120.0 . . ?
C1 C6 H6A 120.0 . . ?
C8 C7 C12 120.0 . . ?
C8 C7 C3 118.0(5) . . ?
C12 C7 C3 121.8(5) . . ?
C9 C8 C7 120.0 . . ?
C9 C8 H8A 120.0 . . ?
C7 C8 H8A 120.0 . . ?
C8 C9 C10 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C10 C9 H9A 120.0 . . ?
C9 C10 C11 120.0 . . ?
C9 C10 H10A 120.0 . . ?
C11 C10 H10A 120.0 . . ?
C10 C11 C12 120.0 . . ?
C10 C11 H11A 120.0 . . ?
C12 C11 H11A 120.0 . . ?
N13 C12 C11 117.6(4) . . ?
N13 C12 C7 121.9(4) . . ?
C11 C12 C7 120.0 . . ?
C12 N13 H13D 120.0 . . ?
C12 N13 H13E 120.0 . . ?
H13D N13 H13E 120.0 . . ?
O26 C14 N15 127.18(18) . . ?
O26 C14 C16 120.15(17) . . ?
N15 C14 C16 112.67(16) . . ?
C14 N15 C19 126.77(16) . . ?
C14 N15 H15A 116.6 . . ?
C19 N15 H15A 116.6 . . ?
O17 C16 N18 127.94(18) . . ?
O17 C16 C14 121.88(17) . . ?
N18 C16 C14 110.18(15) . . ?
C4 N18 C16 133.0(6) . . ?
C16 N18 C4' 126.7(5) . . ?
C4 N18 H18N 115.6 . . ?
C16 N18 H18N 111.3 . . ?
C4' N18 H18N 121.9 . . ?
C20 C19 C24 119.20(18) . . ?
C20 C19 N15 122.94(17) . . ?
C24 C19 N15 117.85(17) . . ?
C19 C20 C21 120.4(2) . . ?
C19 C20 H20A 119.8 . . ?
C21 C20 H20A 119.8 . . ?
C22 C21 C20 119.8(2) . . ?
C22 C21 H21A 120.1 . . ?
C20 C21 H21A 120.1 . . ?
C21 C22 C23 120.79(19) . . ?
C21 C22 Cl25 119.29(16) . . ?
C23 C22 Cl25 119.92(16) . . ?
C22 C23 C24 119.27(19) . . ?
C22 C23 H23A 120.4 . . ?
C24 C23 H23A 120.4 . . ?
C23 C24 C19 120.54(18) . . ?
C23 C24 H24A 119.7 . . ?
C19 C24 H24A 119.7 . . ?
C2' C1' C6' 120.0 . . ?
C2' C1' H1'A 120.0 . . ?
C6' C1' H1'A 120.0 . . ?
C1' C2' C3' 120.0 . . ?
C1' C2' H2'A 120.0 . . ?
C3' C2' H2'A 120.0 . . ?
C4' C3' C2' 120.0 . . ?
C4' C3' C7' 120.3(7) . . ?
C2' C3' C7' 119.7(7) . . ?
C5' C4' C3' 120.0 . . ?
C5' C4' N18 122.6(8) . . ?
C3' C4' N18 117.4(8) . . ?
C4' C5' C6' 120.0 . . ?
C4' C5' H5'A 120.0 . . ?
C6' C5' H5'A 120.0 . . ?
C5' C6' C1' 120.0 . . ?
C5' C6' H6'A 120.0 . . ?
C1' C6' H6'A 120.0 . . ?
C8' C7' C12' 120.0 . . ?
C8' C7' C3' 115.7(5) . . ?
C12' C7' C3' 124.3(5) . . ?
C9' C8' C7' 120.0 . . ?
C9' C8' H8'A 120.0 . . ?
C7' C8' H8'A 120.0 . . ?
C10' C9' C8' 120.0 . . ?
C10' C9' H9'A 120.0 . . ?
C8' C9' H9'A 120.0 . . ?
C9' C10' C11' 120.0 . . ?
C9' C10' H10B 120.0 . . ?
C11' C10' H10B 120.0 . . ?
C12' C11' C10' 120.0 . . ?
C12' C11' H11B 120.0 . . ?
C10' C11' H11B 120.0 . . ?
C11' C12' C7' 120.0 . . ?
C11' C12' N13' 121.6(3) . . ?
C7' C12' N13' 118.3(3) . . ?
C12' N13' H13A 120.0 . . ?
C12' N13' H13C 120.0 . . ?
H13A N13' H13C 120.0 . . ?
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 1.3900 . ?
C1 C6 1.3900 . ?
C1 H1A 0.9500 . ?
C2 C3 1.3900 . ?
C2 H2A 0.9500 . ?
C3 C4 1.3900 . ?
C3 C7 1.506(9) . ?
C4 N18 1.366(11) . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.3900 . ?
C7 C12 1.3900 . ?
C8 C9 1.3900 . ?
C8 H8A 0.9500 . ?
C9 C10 1.3900 . ?
C9 H9A 0.9500 . ?
C10 C11 1.3900 . ?
C10 H10A 0.9500 . ?
C11 C12 1.3900 . ?
C11 H11A 0.9500 . ?
C12 N13 1.299(7) . ?
N13 H13D 0.8800 . ?
N13 H13E 0.8800 . ?
C14 O26 1.224(2) . ?
C14 N15 1.341(2) . ?
C14 C16 1.546(3) . ?
N15 C19 1.413(2) . ?
N15 H15A 0.8800 . ?
C16 O17 1.222(2) . ?
C16 N18 1.342(2) . ?
N18 C4' 1.451(10) . ?
N18 H18N 0.8000 . ?
C19 C20 1.386(3) . ?
C19 C24 1.393(3) . ?
C20 C21 1.391(3) . ?
C20 H20A 0.9500 . ?
C21 C22 1.375(3) . ?
C21 H21A 0.9500 . ?
C22 C23 1.387(3) . ?
C22 Cl25 1.741(2) . ?
C23 C24 1.389(3) . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9500 . ?
C1' C2' 1.3900 . ?
C1' C6' 1.3900 . ?
C1' H1'A 0.9500 . ?
C2' C3' 1.3900 . ?
C2' H2'A 0.9500 . ?
C3' C4' 1.3900 . ?
C3' C7' 1.526(8) . ?
C4' C5' 1.3900 . ?
C5' C6' 1.3900 . ?
C5' H5'A 0.9500 . ?
C6' H6'A 0.9500 . ?
C7' C8' 1.3900 . ?
C7' C12' 1.3900 . ?
C8' C9' 1.3900 . ?
C8' H8'A 0.9500 . ?
C9' C10' 1.3900 . ?
C9' H9'A 0.9500 . ?
C10' C11' 1.3900 . ?
C10' H10B 0.9500 . ?
C11' C12' 1.3900 . ?
C11' H11B 0.9500 . ?
C12' N13' 1.448(7) . ?
N13' H13A 0.8800 . ?
N13' H13C 0.8800 . ?
