#------------------------------------------------------------------------------
#$Date: 2020-08-06 16:44:01 +0200 (Thu 06 de Aug de 2020) $
#$Revision: 255095 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/75/7157546.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_7157546
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'
_chemical_formula_sum            'C20 H16 Cl N3 O2'
_chemical_formula_weight         365.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/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                 117.06(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.174(2)
_cell_length_b                   12.709(3)
_cell_length_c                   12.335(3)
_cell_measurement_reflns_used    2425
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.22
_cell_measurement_theta_min      2.22
_cell_volume                     1699.5(8)
_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 0.999
_diffrn_measured_fraction_theta_max 0.988
_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  0.0232
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14513
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.000
_diffrn_reflns_theta_min         1.878
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_exptl_transmission_factor_max   0.955
_exptl_transmission_factor_min   0.930
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         4465
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0353
_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)+(0.0452P)²+0.7490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0943
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3927
_reflns_number_total             4465
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            d0ob00811g2.cif
_cod_data_source_block           a_a
_cod_depositor_comments
'Adding full bibliography for 7157546--7157547.cif.'
_cod_original_cell_volume        1699.6(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7157546
_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   0.910
_shelx_estimated_absorpt_t_max   0.955
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.61557(11) 0.14344(10) 0.99056(11) 0.0215(2) Uani 1 1 d . . . . .
H1A H 0.660885 0.107708 1.065586 0.026 Uiso 1 1 calc R U . . .
C2 C 0.52073(11) 0.09262(9) 0.89453(10) 0.0188(2) Uani 1 1 d . . . . .
H2A H 0.503446 0.021215 0.903762 0.023 Uiso 1 1 calc R U . . .
C3 C 0.44979(10) 0.14361(9) 0.78443(10) 0.0158(2) Uani 1 1 d . . . . .
C4 C 0.47665(10) 0.24933(9) 0.77569(10) 0.0165(2) Uani 1 1 d . . . . .
C5 C 0.57499(11) 0.29941(9) 0.86964(11) 0.0202(2) Uani 1 1 d . . . . .
H5A H 0.594684 0.370027 0.860098 0.024 Uiso 1 1 calc R U . . .
C6 C 0.64449(11) 0.24630(10) 0.97743(11) 0.0222(2) Uani 1 1 d . . . . .
H6A H 0.711850 0.280422 1.042181 0.027 Uiso 1 1 calc R U . . .
C7 C 0.34891(10) 0.08606(8) 0.68421(10) 0.0156(2) Uani 1 1 d . . . . .
C8 C 0.26141(11) 0.03313(9) 0.70764(11) 0.0190(2) Uani 1 1 d . . . . .
H8A H 0.266156 0.037066 0.786564 0.023 Uiso 1 1 calc R U . . .
C9 C 0.16798(12) -0.02491(10) 0.61818(12) 0.0229(2) Uani 1 1 d . . . . .
H9A H 0.108951 -0.060294 0.635392 0.027 Uiso 1 1 calc R U . . .
C10 C 0.16141(12) -0.03088(10) 0.50335(11) 0.0234(2) Uani 1 1 d . . . . .
H10A H 0.097109 -0.070152 0.441297 0.028 Uiso 1 1 calc R U . . .
C11 C 0.24747(11) 0.01972(9) 0.47833(11) 0.0203(2) Uani 1 1 d . . . . .
H11A H 0.242255 0.014393 0.399301 0.024 Uiso 1 1 calc R U . . .
C12 C 0.34216(11) 0.07869(9) 0.56761(10) 0.0171(2) Uani 1 1 d . . . . .
N13 N 0.42536(11) 0.13266(8) 0.53910(10) 0.0217(2) Uani 1 1 d . . . . .
H13B H 0.4193(15) 0.1160(13) 0.4673(15) 0.025(4) Uiso 1 1 d . . . . .
H13A H 0.5039(17) 0.1286(14) 0.5988(16) 0.033(4) Uiso 1 1 d . . . . .
C14 C 0.34085(11) 0.39502(9) 0.68079(10) 0.0167(2) Uani 1 1 d . . . . .
N15 N 0.39741(9) 0.30856(7) 0.67138(9) 0.01721(19) Uani 1 1 d . . . . .
H15 H 0.3780(16) 0.2823(14) 0.5997(16) 0.029(4) Uiso 1 1 d . . . . .
C16 C 0.24710(10) 0.43877(9) 0.55713(10) 0.0164(2) Uani 1 1 d . . . . .
O17 O 0.35638(9) 0.43868(7) 0.77547(8) 0.02310(19) Uani 1 1 d . . . . .
N18 N 0.18744(9) 0.52098(8) 0.57456(9) 0.0176(2) Uani 1 1 d . . . . .
H18 H 0.2102(15) 0.5362(12) 0.6485(16) 0.023(4) Uiso 1 1 d . . . . .
C19 C 0.09769(10) 0.58615(9) 0.48930(10) 0.0169(2) Uani 1 1 d . . . . .
C20 C 0.05359(12) 0.66963(9) 0.53204(11) 0.0209(2) Uani 1 1 d . . . . .
C21 C -0.03571(12) 0.73739(10) 0.45355(12) 0.0247(3) Uani 1 1 d . . . . .
H21A H -0.065415 0.793033 0.484513 0.030 Uiso 1 1 calc R U . . .
C22 C -0.08148(12) 0.72352(10) 0.32945(12) 0.0246(3) Uani 1 1 d . . . . .
H22A H -0.142432 0.770019 0.274401 0.030 Uiso 1 1 calc R U . . .
C23 C -0.03814(11) 0.64166(10) 0.28584(11) 0.0223(2) Uani 1 1 d . . . . .
H23A H -0.069449 0.632679 0.200451 0.027 Uiso 1 1 calc R U . . .
C24 C 0.04996(11) 0.57252(9) 0.36413(11) 0.0193(2) Uani 1 1 d . . . . .
H24A H 0.077772 0.515979 0.332567 0.023 Uiso 1 1 calc R U . . .
O25 O 0.23328(8) 0.40072(7) 0.46133(8) 0.02170(18) Uani 1 1 d . . . . .
Cl26 Cl 0.11255(4) 0.68855(3) 0.68770(3) 0.03354(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'
Cl Cl 0.1484 0.1585 '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'
H H 0.0000 0.0000 '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 119.98(11) . . ?
C2 C1 H1A 120.0 . . ?
C6 C1 H1A 120.0 . . ?
C1 C2 C3 121.58(11) . . ?
C1 C2 H2A 119.2 . . ?
C3 C2 H2A 119.2 . . ?
C2 C3 C4 117.31(10) . . ?
C2 C3 C7 119.67(10) . . ?
C4 C3 C7 123.00(10) . . ?
C5 C4 C3 121.35(10) . . ?
C5 C4 N15 119.07(10) . . ?
C3 C4 N15 119.47(10) . . ?
C6 C5 C4 119.84(11) . . ?
C6 C5 H5A 120.1 . . ?
C4 C5 H5A 120.1 . . ?
C1 C6 C5 119.78(11) . . ?
C1 C6 H6A 120.1 . . ?
C5 C6 H6A 120.1 . . ?
C8 C7 C12 118.97(11) . . ?
C8 C7 C3 119.10(10) . . ?
C12 C7 C3 121.84(10) . . ?
C9 C8 C7 121.30(11) . . ?
C9 C8 H8A 119.3 . . ?
C7 C8 H8A 119.3 . . ?
C8 C9 C10 119.30(11) . . ?
C8 C9 H9A 120.4 . . ?
C10 C9 H9A 120.4 . . ?
C11 C10 C9 120.50(12) . . ?
C11 C10 H10A 119.8 . . ?
C9 C10 H10A 119.8 . . ?
C10 C11 C12 120.85(11) . . ?
C10 C11 H11A 119.6 . . ?
C12 C11 H11A 119.6 . . ?
N13 C12 C11 119.94(10) . . ?
N13 C12 C7 120.94(11) . . ?
C11 C12 C7 119.07(11) . . ?
C12 N13 H13B 113.4(11) . . ?
C12 N13 H13A 112.8(11) . . ?
H13B N13 H13A 112.3(15) . . ?
O17 C14 N15 126.51(11) . . ?
O17 C14 C16 120.33(10) . . ?
N15 C14 C16 113.16(10) . . ?
C14 N15 C4 121.56(10) . . ?
C14 N15 H15 119.5(11) . . ?
C4 N15 H15 118.3(11) . . ?
O25 C16 N18 128.22(11) . . ?
O25 C16 C14 122.24(10) . . ?
N18 C16 C14 109.53(10) . . ?
C16 N18 C19 129.54(10) . . ?
C16 N18 H18 114.5(11) . . ?
C19 N18 H18 115.9(11) . . ?
C24 C19 N18 123.51(11) . . ?
C24 C19 C20 118.39(11) . . ?
N18 C19 C20 118.10(10) . . ?
C21 C20 C19 121.66(12) . . ?
C21 C20 Cl26 119.19(10) . . ?
C19 C20 Cl26 119.14(9) . . ?
C20 C21 C22 119.33(12) . . ?
C20 C21 H21A 120.3 . . ?
C22 C21 H21A 120.3 . . ?
C23 C22 C21 119.64(12) . . ?
C23 C22 H22A 120.2 . . ?
C21 C22 H22A 120.2 . . ?
C22 C23 C24 121.26(12) . . ?
C22 C23 H23A 119.4 . . ?
C24 C23 H23A 119.4 . . ?
C23 C24 C19 119.71(11) . . ?
C23 C24 H24A 120.1 . . ?
C19 C24 H24A 120.1 . . ?
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 1.3817(18) . ?
C1 C6 1.3823(18) . ?
C1 H1A 0.9500 . ?
C2 C3 1.3939(16) . ?
C2 H2A 0.9500 . ?
C3 C4 1.3985(16) . ?
C3 C7 1.4799(16) . ?
C4 C5 1.3852(17) . ?
C4 N15 1.4226(15) . ?
C5 C6 1.3842(17) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.3967(16) . ?
C7 C12 1.4059(15) . ?
C8 C9 1.3833(18) . ?
C8 H8A 0.9500 . ?
C9 C10 1.3840(18) . ?
C9 H9A 0.9500 . ?
C10 C11 1.3788(18) . ?
C10 H10A 0.9500 . ?
C11 C12 1.3958(17) . ?
C11 H11A 0.9500 . ?
C12 N13 1.3944(15) . ?
N13 H13B 0.881(17) . ?
N13 H13A 0.905(18) . ?
C14 O17 1.2275(14) . ?
C14 N15 1.3296(15) . ?
C14 C16 1.5344(16) . ?
N15 H15 0.871(18) . ?
C16 O25 1.2157(14) . ?
C16 N18 1.3444(15) . ?
N18 C19 1.3930(15) . ?
N18 H18 0.846(17) . ?
C19 C24 1.3912(16) . ?
C19 C20 1.3961(16) . ?
C20 C21 1.3796(18) . ?
C20 Cl26 1.7337(14) . ?
C21 C22 1.3815(19) . ?
C21 H21A 0.9500 . ?
C22 C23 1.3814(19) . ?
C22 H22A 0.9500 . ?
C23 C24 1.3829(17) . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9500 . ?
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
C11 H11A O17 0.95 2.56 3.3641(16) 142.6 4_565
N13 H13B O17 0.881(17) 2.240(17) 3.1012(15) 165.7(14) 4_565
N15 H15 N13 0.871(18) 2.214(18) 2.8776(15) 132.8(15) .
N18 H18 O17 0.846(17) 2.150(16) 2.6131(16) 114.2(13) .
N18 H18 Cl26 0.846(17) 2.433(16) 2.9106(11) 116.5(13) .
