#------------------------------------------------------------------------------
#$Date: 2020-10-06 12:58:10 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257717 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/96/7059649.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_7059649
loop_
_publ_author_name
'Fernandes, Tiago A.'
'André, Vânia'
'Arol, Aliaksandr S.'
'França, Ângela'
'Mikhalyonok, Sergei'
'Cerca, Nuno'
'Kirillov, Alexander M.'
_publ_section_title
;
 New silver (thio)semicarbazide derivatives: synthesis, structural
 features, and antimicrobial activity
;
_journal_issue                   26
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10924
_journal_page_last               10932
_journal_paper_doi               10.1039/D0NJ02013C
_journal_volume                  44
_journal_year                    2020
_chemical_formula_sum            'C14 H12 N4 O2 S'
_chemical_formula_weight         300.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-04-22 deposited with the CCDC.	2020-05-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.932(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.187(3)
_cell_length_b                   34.222(10)
_cell_length_c                   4.7335(14)
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.510
_cell_measurement_theta_min      2.936
_cell_volume                     1415.9(8)
_computing_cell_refinement       'BRUKER SMART (Bruker, 2014)'
_computing_data_collection       'BRUKER SMART (Bruker, 2014)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2014)'
_computing_molecular_graphics    'Mercury 4.1.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            9969
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.510
_diffrn_reflns_theta_min         2.936
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker,2014)'
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2864
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1330
_refine_ls_R_factor_gt           0.0572
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0622P)²+0.3088P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1592
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1432
_reflns_number_total             2864
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj02013c2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7059649--7059651.cif.

 Adding full bibliography for 7059649--7059651.cif.
;
_cod_original_cell_volume        1415.9(7)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C14 H12 N4 O2 S1'
_cod_database_code               7059649
_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   0.958
_shelx_estimated_absorpt_t_max   0.991
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.8747(4) 0.30081(10) 0.0385(7) 0.0583(9) Uani 1 1 d . . . . .
C2 C 0.7427(4) 0.28926(11) 0.0928(8) 0.0664(10) Uani 1 1 d . . . . .
H2 H 0.7021 0.2645 0.0375 0.080 Uiso 1 1 calc R U . . .
C3 C 0.6723(4) 0.31475(10) 0.2293(8) 0.0646(10) Uani 1 1 d . . . . .
H3 H 0.5834 0.3070 0.2685 0.078 Uiso 1 1 calc R U . . .
C4 C 0.7301(3) 0.35207(9) 0.3117(6) 0.0512(8) Uani 1 1 d . . . . .
C5 C 0.8646(4) 0.36251(10) 0.2544(7) 0.0588(9) Uani 1 1 d . . . . .
H5 H 0.9068 0.3871 0.3110 0.071 Uiso 1 1 calc R U . . .
C6 C 0.9360(4) 0.33701(10) 0.1153(8) 0.0642(10) Uani 1 1 d . . . . .
H6 H 1.0249 0.3444 0.0743 0.077 Uiso 1 1 calc R U . . .
C7 C 0.6487(3) 0.37945(9) 0.4518(7) 0.0508(8) Uani 1 1 d . . . . .
C8 C 0.6936(4) 0.42133(10) 0.4926(7) 0.0563(8) Uani 1 1 d D . . . .
C14 C 0.3361(4) 0.37292(11) 0.7309(7) 0.0567(9) Uani 1 1 d . . . . .
N1 N 0.9483(4) 0.27361(10) -0.1116(8) 0.0767(10) Uani 1 1 d . . . . .
N2 N 0.5375(3) 0.36420(7) 0.5274(6) 0.0550(7) Uani 1 1 d . . . . .
N3 N 0.4559(3) 0.38756(8) 0.6547(6) 0.0575(7) Uani 1 1 d . . . . .
N4 N 0.3118(4) 0.33518(10) 0.6870(8) 0.0777(11) Uani 1 1 d . . . . .
O1 O 1.0560(3) 0.28460(8) -0.1872(7) 0.1047(11) Uani 1 1 d . . . . .
O2 O 0.8957(4) 0.24074(10) -0.1617(8) 0.1141(12) Uani 1 1 d . . . . .
S1 S 0.23157(11) 0.40195(3) 0.8721(2) 0.0773(4) Uani 1 1 d . . . . .
C11 C 0.7814(5) 0.50014(14) 0.5669(14) 0.0974(15) Uani 1 1 d . . . . .
H11 H 0.8225 0.5252 0.5919 0.117 Uiso 1 1 calc R U . A 1
C13 C 0.8370(6) 0.42844(13) 0.6669(11) 0.0584(12) Uani 0.7 1 d . . P B 2
H13 H 0.9040 0.4085 0.7563 0.070 Uiso 0.7 1 calc R U P B 2
C9 C 0.5935(7) 0.44721(13) 0.3486(14) 0.0758(17) Uani 0.7 1 d . . P B 2
H9 H 0.4972 0.4398 0.2271 0.091 Uiso 0.7 1 calc R U P B 2
C12 C 0.8781(6) 0.46721(14) 0.7041(15) 0.0808(17) Uani 0.7 1 d . . P B 2
H12 H 0.9760 0.4729 0.8276 0.097 Uiso 0.7 1 calc R U P B 2
C10 C 0.6362(8) 0.48594(15) 0.3837(19) 0.111(3) Uani 0.7 1 d . . P B 2
H10 H 0.5652 0.5043 0.2803 0.133 Uiso 0.7 1 calc R U P B 2
C12A C 0.7864(12) 0.4860(3) 0.807(2) 0.043(2) Uani 0.3 1 d . . P B 1
H12A H 0.8148 0.4998 0.9849 0.051 Uiso 0.3 1 calc R U P B 1
C13A C 0.7441(11) 0.4465(3) 0.780(2) 0.042(2) Uani 0.3 1 d D . P B 1
H13A H 0.7466 0.4338 0.9550 0.051 Uiso 0.3 1 calc R U P B 1
C10A C 0.7389(14) 0.4913(3) 0.304(3) 0.048(3) Uani 0.3 1 d . . P B 1
H10A H 0.7357 0.5086 0.1505 0.058 Uiso 0.3 1 calc R U P B 1
C9A C 0.6960(12) 0.4524(3) 0.262(2) 0.045(2) Uani 0.3 1 d . . P B 1
H9A H 0.6641 0.4440 0.0657 0.053 Uiso 0.3 1 calc R U P B 1
H1N H 0.360(4) 0.3239(9) 0.592(7) 0.053 Uiso 1 1 d . U . . .
H2N H 0.247(4) 0.3248(9) 0.742(7) 0.053 Uiso 1 1 d . U . . .
H3N H 0.464(3) 0.4129(8) 0.670(7) 0.053 Uiso 1 1 d . 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
C6 C1 C2 121.9(3) . . ?
C6 C1 N1 119.7(3) . . ?
C2 C1 N1 118.4(3) . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 117.8(3) . . ?
C5 C4 C7 121.8(3) . . ?
C3 C4 C7 120.4(3) . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C1 C6 C5 119.0(3) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
N2 C7 C4 114.9(3) . . ?
N2 C7 C8 124.4(3) . . ?
C4 C7 C8 120.7(2) . . ?
C9 C8 C13 126.6(4) . . ?
C9 C8 C7 117.6(3) . . ?
C13 C8 C7 115.7(3) . . ?
C7 C8 C9A 129.9(5) . . ?
C7 C8 C13A 130.0(4) . . ?
C9A C8 C13A 100.0(5) . . ?
N4 C14 N3 115.6(3) . . ?
N4 C14 S1 124.1(2) . . ?
N3 C14 S1 120.3(3) . . ?
O1 N1 O2 122.7(3) . . ?
O1 N1 C1 119.3(3) . . ?
O2 N1 C1 118.0(3) . . ?
C7 N2 N3 118.5(3) . . ?
C14 N3 N2 120.4(3) . . ?
C14 N3 H3N 114(2) . . ?
N2 N3 H3N 125(2) . . ?
C14 N4 H1N 117(2) . . ?
C14 N4 H2N 119(2) . . ?
H1N N4 H2N 123(3) . . ?
C12A C11 C10A 139.3(8) . . ?
C10 C11 C12 109.5(4) . . ?
C12A C11 H11 110.4 . . ?
C10A C11 H11 110.4 . . ?
C8 C13 C12 115.6(4) . . ?
C8 C13 H13 122.2 . . ?
C12 C13 H13 122.2 . . ?
C8 C9 C10 117.4(5) . . ?
C8 C9 H9 121.3 . . ?
C10 C9 H9 121.3 . . ?
C13 C12 C11 125.7(5) . . ?
C13 C12 H12 117.2 . . ?
C11 C12 H12 117.2 . . ?
C9 C10 C11 125.2(5) . . ?
C9 C10 H10 117.4 . . ?
C11 C10 H10 117.4 . . ?
C11 C12A C13A 111.5(8) . . ?
C11 C12A H12A 124.3 . . ?
C13A C12A H12A 124.3 . . ?
C12A C13A C8 127.8(8) . . ?
C12A C13A H13A 116.1 . . ?
C8 C13A H13A 116.1 . . ?
C11 C10A C9A 111.8(9) . . ?
C11 C10A H10A 124.1 . . ?
C9A C10A H10A 124.1 . . ?
C10A C9A C8 129.2(9) . . ?
C10A C9A H9A 115.4 . . ?
C8 C9A H9A 115.4 . . ?
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 C6 1.363(4) . ?
C1 C2 1.373(4) . ?
C1 N1 1.457(4) . ?
C2 C3 1.361(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(4) . ?
C4 C7 1.477(4) . ?
C5 C6 1.375(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N2 1.292(3) . ?
C7 C8 1.487(4) . ?
C8 C9 1.307(6) . ?
C8 C13 1.344(5) . ?
C8 C9A 1.529(9) . ?
C8 C13A 1.555(9) . ?
C14 N4 1.316(5) . ?
C14 N3 1.356(4) . ?
C14 S1 1.658(3) . ?
N1 O1 1.211(3) . ?
N1 O2 1.218(4) . ?
N2 N3 1.357(3) . ?
N3 H3N 0.87(3) . ?
N4 H1N 0.82(3) . ?
N4 H2N 0.80(3) . ?
C11 C12A 1.222(11) . ?
C11 C10A 1.222(12) . ?
C11 C10 1.434(7) . ?
C11 C12 1.458(7) . ?
C11 H11 0.9300 . ?
C13 C12 1.376(6) . ?
C13 H13 0.9300 . ?
C9 C10 1.378(7) . ?
C9 H9 0.9300 . ?
C12 H12 0.9300 . ?
C10 H10 0.9300 . ?
C12A C13A 1.404(12) . ?
C12A H12A 0.9300 . ?
C13A H13A 0.9300 . ?
C10A C9A 1.386(14) . ?
C10A H10A 0.9300 . ?
C9A H9A 0.9300 . ?
