#------------------------------------------------------------------------------
#$Date: 2020-12-06 10:47:19 +0200 (Sun, 06 Dec 2020) $
#$Revision: 259597 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/16/7241697.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_7241697
loop_
_publ_author_name
'Liu, Hong-Yan'
'Chen, Yu'
'Hao, Li-Qiang'
'Wang, Guo-Dong'
'Li, Hong-Shuang'
'Xia, Cheng-Cai'
_publ_section_title
;
 The synthesis of
 N,N′-disulfanediyl-bis(N′-((E)-benzylidene)acetohydrazide)
 from (E)-N′-benzylideneacetohydrazide and S8
;
_journal_issue                   67
_journal_name_full               'RSC Advances'
_journal_page_first              41041
_journal_page_last               41046
_journal_paper_doi               10.1039/D0RA08441G
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C22 H26 N4 O2 S2'
_chemical_formula_sum            'C22 H26 N4 O2 S2'
_chemical_formula_weight         442.59
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-06-06 deposited with the CCDC.	2020-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                99.224(8)
_cell_angle_beta                 106.772(7)
_cell_angle_gamma                111.122(7)
_cell_formula_units_Z            2
_cell_length_a                   10.094(5)
_cell_length_b                   11.277(5)
_cell_length_c                   11.815(5)
_cell_measurement_reflns_used    3252
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.13
_cell_measurement_theta_min      2.32
_cell_volume                     1147.4(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0192
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6883
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         1.885
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0475
_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)+(0.0715P)²+0.5393P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1429
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3421
_reflns_number_total             4258
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra08441g2.cif
_cod_data_source_block           1
_cod_database_code               7241697
_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   0.948
_shelx_estimated_absorpt_t_max   0.970
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
S1 S 1.23835(8) 0.67381(7) 1.04692(6) 0.0657(2) Uani 1 1 d . . . . .
S2 S 1.18744(8) 0.81695(6) 1.12481(5) 0.0614(2) Uani 1 1 d . . . . .
O1 O 1.5362(2) 0.8496(3) 1.0606(2) 0.1018(8) Uani 1 1 d . . . . .
O2 O 0.9385(3) 0.64184(19) 1.17586(17) 0.0768(6) Uani 1 1 d . . . . .
N1 N 1.1880(2) 0.6901(2) 0.81013(18) 0.0531(5) Uani 1 1 d . . . . .
N2 N 1.2905(2) 0.7208(2) 0.93039(19) 0.0605(5) Uani 1 1 d . . . . .
N3 N 0.9317(2) 0.79881(19) 0.94557(17) 0.0507(5) Uani 1 1 d . . . . .
N4 N 0.9961(2) 0.7640(2) 1.04835(17) 0.0532(5) Uani 1 1 d . . . . .
C1 C 1.0481(3) 0.6152(2) 0.7810(2) 0.0484(5) Uani 1 1 d . . . . .
H1 H 1.0152 0.5791 0.8388 0.058 Uiso 1 1 calc R U . . .
C2 C 0.9376(3) 0.5852(2) 0.6571(2) 0.0461(5) Uani 1 1 d . . . . .
C3 C 0.9808(3) 0.6382(3) 0.5683(2) 0.0582(6) Uani 1 1 d . . . . .
H3 H 1.0835 0.6919 0.5865 0.070 Uiso 1 1 calc R U . . .
C4 C 0.8737(3) 0.6123(3) 0.4543(2) 0.0610(6) Uani 1 1 d . . . . .
H4 H 0.9053 0.6484 0.3960 0.073 Uiso 1 1 calc R U . . .
C5 C 0.7196(3) 0.5336(2) 0.4239(2) 0.0525(6) Uani 1 1 d . . . . .
C6 C 0.6774(3) 0.4782(2) 0.5108(2) 0.0609(6) Uani 1 1 d . . . . .
H6 H 0.5750 0.4227 0.4917 0.073 Uiso 1 1 calc R U . . .
C7 C 0.7853(3) 0.5039(2) 0.6264(2) 0.0578(6) Uani 1 1 d . . . . .
H7 H 0.7543 0.4656 0.6839 0.069 Uiso 1 1 calc R U . . .
C8 C 0.6037(3) 0.5148(3) 0.3011(2) 0.0656(7) Uani 1 1 d . . . . .
H8A H 0.6349 0.4858 0.2355 0.079 Uiso 1 1 calc R U . . .
H8B H 0.5053 0.4455 0.2890 0.079 Uiso 1 1 calc R U . . .
C9 C 0.5862(3) 0.6402(3) 0.2922(3) 0.0740(8) Uani 1 1 d . . . . .
H9A H 0.5114 0.6237 0.2126 0.111 Uiso 1 1 calc R U . . .
H9B H 0.5533 0.6684 0.3559 0.111 Uiso 1 1 calc R U . . .
H9C H 0.6828 0.7087 0.3023 0.111 Uiso 1 1 calc R U . . .
C10 C 1.4422(3) 0.8097(3) 0.9569(3) 0.0721(8) Uani 1 1 d . . . . .
C11 C 1.4777(4) 0.8491(3) 0.8513(3) 0.0900(10) Uani 1 1 d . . . . .
H11A H 1.3866 0.8059 0.7775 0.135 Uiso 1 1 calc R U . . .
H11B H 1.5149 0.9439 0.8682 0.135 Uiso 1 1 calc R U . . .
H11C H 1.5547 0.8230 0.8398 0.135 Uiso 1 1 calc R U . . .
C12 C 1.0173(3) 0.8730(2) 0.9015(2) 0.0487(5) Uani 1 1 d . . . . .
H12 H 1.1231 0.9046 0.9379 0.058 Uiso 1 1 calc R U . . .
C13 C 0.9493(3) 0.9088(2) 0.79317(19) 0.0442(5) Uani 1 1 d . . . . .
C14 C 1.0436(3) 1.0003(2) 0.7523(2) 0.0520(5) Uani 1 1 d . . . . .
H14 H 1.1495 1.0364 0.7924 0.062 Uiso 1 1 calc R U . . .
C15 C 0.9801(3) 1.0379(2) 0.6519(2) 0.0555(6) Uani 1 1 d . . . . .
H15 H 1.0447 1.0995 0.6254 0.067 Uiso 1 1 calc R U . . .
C16 C 0.8243(3) 0.9866(2) 0.5903(2) 0.0524(6) Uani 1 1 d . . . . .
C17 C 0.7311(3) 0.8928(3) 0.6297(2) 0.0599(6) Uani 1 1 d . . . . .
H17 H 0.6253 0.8551 0.5881 0.072 Uiso 1 1 calc R U . . .
C18 C 0.7923(3) 0.8545(2) 0.7295(2) 0.0557(6) Uani 1 1 d . . . . .
H18 H 0.7274 0.7913 0.7545 0.067 Uiso 1 1 calc R U . . .
C19 C 0.7551(4) 1.0325(3) 0.4847(3) 0.0699(7) Uani 1 1 d . . . . .
H19A H 0.8285 1.0652 0.4464 0.084 Uiso 1 1 calc R U . . .
H19B H 0.6651 0.9574 0.4229 0.084 Uiso 1 1 calc R U . . .
C20 C 0.7107(4) 1.1403(3) 0.5265(3) 0.0761(8) Uani 1 1 d . . . . .
H20A H 0.6674 1.1665 0.4567 0.114 Uiso 1 1 calc R U . . .
H20B H 0.6365 1.1078 0.5630 0.114 Uiso 1 1 calc R U . . .
H20C H 0.7999 1.2156 0.5865 0.114 Uiso 1 1 calc R U . . .
C21 C 0.8922(3) 0.6799(2) 1.0898(2) 0.0586(6) Uani 1 1 d . . . . .
C22 C 0.7266(3) 0.6424(3) 1.0222(3) 0.0748(8) Uani 1 1 d . . . . .
H22A H 0.7157 0.6838 0.9572 0.112 Uiso 1 1 calc R U . . .
H22B H 0.6725 0.5475 0.9872 0.112 Uiso 1 1 calc R U . . .
H22C H 0.6851 0.6720 1.0786 0.112 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
N2 S1 S2 106.04(8) . . ?
N4 S2 S1 105.31(8) . . ?
C1 N1 N2 119.2(2) . . ?
N1 N2 C10 115.6(2) . . ?
N1 N2 S1 124.35(17) . . ?
C10 N2 S1 119.6(2) . . ?
C12 N3 N4 119.8(2) . . ?
N3 N4 C21 115.9(2) . . ?
N3 N4 S2 124.66(16) . . ?
C21 N4 S2 119.46(16) . . ?
N1 C1 C2 120.3(2) . . ?
N1 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C7 C2 C3 118.2(2) . . ?
C7 C2 C1 119.9(2) . . ?
C3 C2 C1 122.0(2) . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 121.5(2) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 117.8(2) . . ?
C6 C5 C8 122.0(2) . . ?
C4 C5 C8 120.1(2) . . ?
C5 C6 C7 120.9(2) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C2 C7 C6 120.9(2) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C9 C8 C5 112.3(2) . . ?
C9 C8 H8A 109.1 . . ?
C5 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C5 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 N2 120.2(3) . . ?
O1 C10 C11 123.3(3) . . ?
N2 C10 C11 116.4(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C13 119.7(2) . . ?
N3 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C18 C13 C14 118.5(2) . . ?
C18 C13 C12 122.0(2) . . ?
C14 C13 C12 119.5(2) . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 121.7(2) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C17 118.0(2) . . ?
C15 C16 C19 121.6(2) . . ?
C17 C16 C19 120.4(2) . . ?
C18 C17 C16 121.1(2) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C13 120.8(2) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
C20 C19 C16 112.2(2) . . ?
C20 C19 H19A 109.2 . . ?
C16 C19 H19A 109.2 . . ?
C20 C19 H19B 109.2 . . ?
C16 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C21 N4 120.0(3) . . ?
O2 C21 C22 123.4(3) . . ?
N4 C21 C22 116.6(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 N2 1.704(2) . ?
S1 S2 2.0276(11) . ?
S2 N4 1.701(2) . ?
O1 C10 1.204(4) . ?
O2 C21 1.203(3) . ?
N1 C1 1.262(3) . ?
N1 N2 1.394(3) . ?
N2 C10 1.402(4) . ?
N3 C12 1.263(3) . ?
N3 N4 1.390(2) . ?
N4 C21 1.402(3) . ?
C1 C2 1.459(3) . ?
C1 H1 0.9300 . ?
C2 C7 1.375(3) . ?
C2 C3 1.387(3) . ?
C3 C4 1.369(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(3) . ?
C5 C8 1.504(3) . ?
C6 C7 1.387(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.503(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.484(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.460(3) . ?
C12 H12 0.9300 . ?
C13 C18 1.385(3) . ?
C13 C14 1.386(3) . ?
C14 C15 1.385(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(3) . ?
C16 C19 1.509(3) . ?
C17 C18 1.376(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.500(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.491(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C22 H22B S1 0.96 2.95 3.695(3) 135.3 2_767
C22 H22A N3 0.96 2.16 2.679(4) 112.8 .
C11 H11B O1 0.96 2.62 3.456(5) 145.2 2_877
C11 H11A N1 0.96 2.14 2.669(4) 113.0 .
C11 H11A N1 0.96 2.14 2.669(4) 113.0 .
C11 H11B O1 0.96 2.62 3.456(5) 145.2 2_877
C22 H22A N3 0.96 2.16 2.679(4) 112.8 .
C22 H22B S1 0.96 2.95 3.695(3) 135.3 2_767
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
C1 N1 N2 C10 -177.0(2) . . . . ?
C1 N1 N2 S1 -5.0(3) . . . . ?
S2 S1 N2 N1 -86.80(18) . . . . ?
S2 S1 N2 C10 84.88(19) . . . . ?
C12 N3 N4 C21 -179.18(19) . . . . ?
C12 N3 N4 S2 1.4(3) . . . . ?
S1 S2 N4 N3 -93.25(17) . . . . ?
S1 S2 N4 C21 87.32(17) . . . . ?
N2 N1 C1 C2 177.88(18) . . . . ?
N1 C1 C2 C7 -179.8(2) . . . . ?
N1 C1 C2 C3 -0.9(3) . . . . ?
C7 C2 C3 C4 1.4(4) . . . . ?
C1 C2 C3 C4 -177.5(2) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 C6 -2.0(4) . . . . ?
C3 C4 C5 C8 175.7(2) . . . . ?
C4 C5 C6 C7 1.9(4) . . . . ?
C8 C5 C6 C7 -175.8(2) . . . . ?
C3 C2 C7 C6 -1.5(4) . . . . ?
C1 C2 C7 C6 177.4(2) . . . . ?
C5 C6 C7 C2 -0.2(4) . . . . ?
C6 C5 C8 C9 108.9(3) . . . . ?
C4 C5 C8 C9 -68.7(3) . . . . ?
N1 N2 C10 O1 174.6(2) . . . . ?
S1 N2 C10 O1 2.2(3) . . . . ?
N1 N2 C10 C11 -5.8(3) . . . . ?
S1 N2 C10 C11 -178.2(2) . . . . ?
N4 N3 C12 C13 179.66(18) . . . . ?
N3 C12 C13 C18 -5.9(3) . . . . ?
N3 C12 C13 C14 173.8(2) . . . . ?
C18 C13 C14 C15 1.6(3) . . . . ?
C12 C13 C14 C15 -178.1(2) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
C14 C15 C16 C17 -1.6(4) . . . . ?
C14 C15 C16 C19 177.1(2) . . . . ?
C15 C16 C17 C18 1.7(4) . . . . ?
C19 C16 C17 C18 -177.0(2) . . . . ?
C16 C17 C18 C13 -0.1(4) . . . . ?
C14 C13 C18 C17 -1.5(4) . . . . ?
C12 C13 C18 C17 178.2(2) . . . . ?
C15 C16 C19 C20 -95.2(3) . . . . ?
C17 C16 C19 C20 83.4(3) . . . . ?
N3 N4 C21 O2 177.7(2) . . . . ?
S2 N4 C21 O2 -2.8(3) . . . . ?
N3 N4 C21 C22 -2.3(3) . . . . ?
S2 N4 C21 C22 177.21(18) . . . . ?
