#------------------------------------------------------------------------------
#$Date: 2021-06-05 22:26:55 +0300 (Sat, 05 Jun 2021) $
#$Revision: 266156 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/79/7157992.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_7157992
loop_
_publ_author_name
'Wei, Yueting'
'Liu, Ping'
'Liu, Yali'
'He, Jing'
'Li, Xuezhen'
'Li, Shiwu'
'Zhao, Jixing'
_publ_section_title
;
 NIS-promoted three-component reaction of 3-oxo-3-arylpropanenitriles with
 arylsulfonyl hydrazides.
;
_journal_issue                   17
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3932
_journal_page_last               3939
_journal_paper_doi               10.1039/d1ob00438g
_journal_volume                  19
_journal_year                    2021
_chemical_formula_sum            'C21 H17 N3 O2 S2'
_chemical_formula_weight         407.49
_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-2018/3
_audit_update_record
;
2020-10-05 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.402(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.019(2)
_cell_length_b                   19.073(2)
_cell_length_c                   10.6129(11)
_cell_measurement_reflns_used    6877
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.78
_cell_measurement_theta_min      2.37
_cell_volume                     3832.7(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0925
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18537
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.371
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.799
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3577
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0773
_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)+(0.0850P)²+12.4343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1814
_refine_ls_wR_factor_ref         0.1997
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2701
_reflns_number_total             3577
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00438g1.cif
_cod_data_source_block           11_a
_cod_depositor_comments
'Adding full bibliography for 7157992--7157994.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7157992
_shelx_shelxl_version_number     2018/3
_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   0.923
_shelx_estimated_absorpt_t_max   0.934
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 0.90207(6) 0.44683(5) 0.28399(9) 0.0431(3) Uani 1 1 d . . . . .
O1 O 0.93130(16) 0.51147(14) 0.3323(3) 0.0486(7) Uani 1 1 d . . . . .
N1 N 0.8001(2) 0.5383(2) 0.4325(4) 0.0513(9) Uani 1 1 d D . . . .
H1B H 0.8456(7) 0.544(3) 0.438(5) 0.059(15) Uiso 1 1 d D . . . .
H1A H 0.772(2) 0.553(3) 0.487(4) 0.061(15) Uiso 1 1 d D . . . .
C1 C 0.9059(2) 0.3848(2) 0.4060(4) 0.0409(9) Uani 1 1 d . . . . .
S2 S 0.63759(6) 0.47869(6) 0.41711(11) 0.0519(3) Uani 1 1 d . . . . .
O2 O 0.92204(16) 0.41759(16) 0.1697(3) 0.0507(8) Uani 1 1 d . . . . .
N2 N 0.81442(19) 0.46096(17) 0.2591(3) 0.0435(8) Uani 1 1 d . . . . .
C2 C 0.8835(2) 0.3167(2) 0.3775(4) 0.0481(10) Uani 1 1 d . . . . .
H2 H 0.871444 0.302615 0.292342 0.058 Uiso 1 1 calc R U . . .
N3 N 0.77621(19) 0.40954(17) 0.1881(3) 0.0444(8) Uani 1 1 d . . . . .
C3 C 0.8792(3) 0.2699(2) 0.4764(4) 0.0521(11) Uani 1 1 d . . . . .
H3A H 0.863928 0.223154 0.459067 0.063 Uiso 1 1 calc R U . . .
C4 C 0.8971(2) 0.2908(2) 0.6005(4) 0.0491(11) Uani 1 1 d . . . . .
H4 H 0.893568 0.258417 0.667628 0.059 Uiso 1 1 calc R U . . .
C5 C 0.9200(2) 0.3582(2) 0.6269(4) 0.0474(10) Uani 1 1 d . . . . .
H5 H 0.932489 0.371943 0.712083 0.057 Uiso 1 1 calc R U . . .
C6 C 0.9248(2) 0.4062(2) 0.5294(4) 0.0469(10) Uani 1 1 d . . . . .
H6 H 0.940723 0.452747 0.546975 0.056 Uiso 1 1 calc R U . . .
C7 C 0.7741(2) 0.4901(2) 0.3482(4) 0.0447(10) Uani 1 1 d . . . . .
C9 C 0.7132(2) 0.4091(2) 0.2295(4) 0.0428(9) Uani 1 1 d . . . . .
C8 C 0.7082(2) 0.4593(2) 0.3301(4) 0.0435(10) Uani 1 1 d . . . . .
C10 C 0.6607(2) 0.3595(2) 0.1703(4) 0.0445(10) Uani 1 1 d . . . . .
C11 C 0.6855(3) 0.2959(2) 0.1259(4) 0.0494(11) Uani 1 1 d . . . . .
H11 H 0.734343 0.284945 0.138760 0.059 Uiso 1 1 calc R U . . .
C12 C 0.6389(3) 0.2487(2) 0.0633(4) 0.0565(12) Uani 1 1 d . . . . .
H12 H 0.656257 0.206084 0.031832 0.068 Uiso 1 1 calc R U . . .
C13 C 0.5680(3) 0.2633(3) 0.0465(4) 0.0602(13) Uani 1 1 d . . . . .
H13 H 0.536277 0.230623 0.004232 0.072 Uiso 1 1 calc R U . . .
C14 C 0.5428(3) 0.3261(3) 0.0916(5) 0.0627(13) Uani 1 1 d . . . . .
H14 H 0.493729 0.336481 0.080142 0.075 Uiso 1 1 calc R U . . .
C15 C 0.5895(3) 0.3734(3) 0.1534(4) 0.0549(11) Uani 1 1 d . . . . .
H15 H 0.572045 0.416058 0.184468 0.066 Uiso 1 1 calc R U . . .
C16 C 0.6531(2) 0.4254(2) 0.5547(4) 0.0433(9) Uani 1 1 d . . . . .
C17 C 0.5966(3) 0.4174(2) 0.6275(4) 0.0486(10) Uani 1 1 d . . . . .
H17 H 0.552207 0.438118 0.601182 0.058 Uiso 1 1 calc R U . . .
C18 C 0.6054(3) 0.3792(2) 0.7386(4) 0.0560(12) Uani 1 1 d . . . . .
H18 H 0.566862 0.373162 0.788277 0.067 Uiso 1 1 calc R U . . .
C19 C 0.6697(3) 0.3500(2) 0.7770(4) 0.0547(12) Uani 1 1 d . . . . .
H19 H 0.675630 0.324630 0.854278 0.066 Uiso 1 1 calc R U . . .
C20 C 0.7256(3) 0.3571(2) 0.7050(4) 0.0489(10) Uani 1 1 d . . . . .
H20 H 0.769688 0.335941 0.731932 0.059 Uiso 1 1 calc R U . . .
C21 C 0.7179(2) 0.3954(2) 0.5923(4) 0.0456(10) Uani 1 1 d . . . . .
H21 H 0.756433 0.400789 0.542351 0.055 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 0.0033 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'
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
O2 S1 O1 121.33(18) . . ?
O2 S1 N2 105.62(17) . . ?
O1 S1 N2 105.32(18) . . ?
O2 S1 C1 111.75(19) . . ?
O1 S1 C1 109.30(18) . . ?
N2 S1 C1 101.30(18) . . ?
C7 N1 H1B 116(3) . . ?
C7 N1 H1A 116(3) . . ?
H1B N1 H1A 126(5) . . ?
C6 C1 C2 121.9(4) . . ?
C6 C1 S1 119.2(3) . . ?
C2 C1 S1 118.7(3) . . ?
C8 S2 C16 103.7(2) . . ?
C7 N2 N3 110.8(3) . . ?
C7 N2 S1 124.0(3) . . ?
N3 N2 S1 115.4(3) . . ?
C3 C2 C1 118.4(4) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C9 N3 N2 105.6(3) . . ?
C2 C3 C4 120.5(4) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C5 C4 C3 120.4(4) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.3(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.6(4) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
N1 C7 C8 131.0(4) . . ?
N1 C7 N2 122.3(4) . . ?
C8 C7 N2 106.7(4) . . ?
N3 C9 C8 111.6(4) . . ?
N3 C9 C10 117.7(4) . . ?
C8 C9 C10 130.8(4) . . ?
C7 C8 C9 105.3(4) . . ?
C7 C8 S2 124.8(3) . . ?
C9 C8 S2 129.8(3) . . ?
C15 C10 C11 118.7(4) . . ?
C15 C10 C9 123.5(4) . . ?
C11 C10 C9 117.7(4) . . ?
C12 C11 C10 120.3(5) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 120.4(5) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.7(5) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 119.7(5) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C10 C15 C14 121.1(5) . . ?
C10 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C21 C16 C17 120.6(4) . . ?
C21 C16 S2 123.1(3) . . ?
C17 C16 S2 116.2(3) . . ?
C18 C17 C16 119.6(4) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C19 C18 C17 120.1(4) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 120.7(4) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C21 120.2(4) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C16 C21 C20 118.8(4) . . ?
C16 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
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 1.419(3) . ?
S1 O1 1.428(3) . ?
S1 N2 1.685(4) . ?
S1 C1 1.751(4) . ?
N1 C7 1.344(6) . ?
N1 H1B 0.869(10) . ?
N1 H1A 0.869(10) . ?
C1 C6 1.387(6) . ?
C1 C2 1.391(6) . ?
S2 C8 1.740(4) . ?
S2 C16 1.781(4) . ?
N2 C7 1.389(5) . ?
N2 N3 1.398(5) . ?
C2 C3 1.386(6) . ?
C2 H2 0.9500 . ?
N3 C9 1.315(5) . ?
C3 C4 1.387(6) . ?
C3 H3A 0.9500 . ?
C4 C5 1.377(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.380(6) . ?
C9 C8 1.444(6) . ?
C9 C10 1.471(6) . ?
C10 C15 1.375(6) . ?
C10 C11 1.399(6) . ?
C11 C12 1.387(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.372(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(7) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.382(6) . ?
C16 C17 1.389(6) . ?
C17 C18 1.382(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.369(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.374(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.398(6) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
