#------------------------------------------------------------------------------
#$Date: 2023-02-15 14:11:53 +0200 (Wed, 15 Feb 2023) $
#$Revision: 280922 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/84/1568402.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_1568402
loop_
_publ_author_name
'Silvia Gutiérrez-Tarriño'
'Javier Espino'
'Francisco Luna-Giles'
'Ana B. Rodríguez'
'Jos'e A. Pariente'
'Emilio Viñuelas-Zahínos'
_publ_section_title
;
 Synthesis, Characterization and Antiproliferative Evaluation of Pt(II)
 and Pd(II) Complexes with a Thiazine-Pyridine Derivative Ligand
;
_journal_name_full               Pharmaceuticals
_journal_page_first              395
_journal_paper_doi               10.3390/ph14050395
_journal_volume                  14
_journal_year                    2021
_chemical_formula_moiety         'C9 H12 N3 S, Cl, 2(H2 O)'
_chemical_formula_sum            'C9 H16 Cl N3 O2 S'
_chemical_formula_weight         265.76
_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   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                96.00
_cell_angle_beta                 97.83
_cell_angle_gamma                101.18
_cell_formula_units_Z            2
_cell_length_a                   6.968
_cell_length_b                   9.577
_cell_length_c                   9.593
_cell_measurement_reflns_used    9843
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      36.405
_cell_measurement_theta_min      2.86
_cell_volume                     616.489
_computing_cell_refinement       'BRUKER APEX2'
_computing_data_collection       'BRUKER APEX2'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            57032
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.568
_diffrn_reflns_theta_min         2.163
_exptl_absorpt_coefficient_mu    0.470
_exptl_absorpt_correction_T_max  0.888
_exptl_absorpt_correction_T_min  0.830
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       plate
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.590
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.622
_refine_diff_density_min         -1.210
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         6033
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0422
_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)+(0.0528P)²+0.6803P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1295
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5254
_reflns_number_total             6033
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            PyTzHCl.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        616.5
_cod_database_code               1568402
_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   0.769
_shelx_estimated_absorpt_t_max   0.950
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
Cl1 Cl 0.21871(5) 0.77980(3) 0.91931(3) 0.01864(7) Uani 1 1 d . . . . .
S1 S 0.16855(6) 0.15915(4) 0.66057(4) 0.01469(9) Uani 0.8193(15) 1 d . . P A 1
S1A S 0.2209(9) 0.4143(6) 0.9061(6) 0.01469(9) Uani 0.1807(15) 1 d . . P A 2
O1W O 0.39165(18) 0.03500(13) 0.16873(12) 0.0250(2) Uani 1 1 d D . . . .
N1 N 0.23210(19) 0.44188(13) 0.76420(13) 0.0133(2) Uani 0.8193(15) 1 d . . P A 1
H1 H 0.2512 0.5322 0.7490 0.016 Uiso 0.8193(15) 1 calc R U P A 1
N2 N 0.2232(2) 0.37763(14) 0.52264(13) 0.0147(2) Uani 0.8193(15) 1 d . . P A 1
H2 H 0.2085 0.3051 0.4550 0.018 Uiso 0.8193(15) 1 calc R U P A 1
N3 N 0.2850(2) 0.62798(17) 0.58027(17) 0.0166(2) Uani 0.8193(15) 1 d . . P A 1
C1 C 0.2111(2) 0.34388(18) 0.65527(16) 0.0122(2) Uani 0.8193(15) 1 d . . P A 1
C4 C 0.1429(2) 0.14972(17) 0.84436(17) 0.0167(2) Uani 0.8193(15) 1 d . . P A 1
H4A H 0.0031 0.1474 0.8554 0.020 Uiso 0.8193(15) 1 calc R U P A 1
H4B H 0.1765 0.0595 0.8718 0.020 Uiso 0.8193(15) 1 calc R U P A 1
C3 C 0.2754(2) 0.27612(17) 0.94284(16) 0.0163(2) Uani 0.8193(15) 1 d . . P A 1
H3A H 0.2564 0.2671 1.0422 0.020 Uiso 0.8193(15) 1 calc R U P A 1
H3B H 0.4159 0.2765 0.9359 0.020 Uiso 0.8193(15) 1 calc R U P A 1
C2 C 0.2264(12) 0.4133(7) 0.9035(7) 0.0302(7) Uani 0.8193(15) 1 d . . P A 1
H2A H 0.0915 0.4155 0.9240 0.036 Uiso 0.8193(15) 1 calc R U P A 1
H2B H 0.3188 0.4933 0.9674 0.036 Uiso 0.8193(15) 1 calc R U P A 1
C5 C 0.2565(2) 0.51515(17) 0.48105(18) 0.0133(2) Uani 0.8193(15) 1 d . . P A 1
N1A N 0.2068(10) 0.3032(7) 0.6213(8) 0.0133(2) Uani 0.1807(15) 1 d . . P A 2
H1A H 0.2518 0.3153 0.5411 0.016 Uiso 0.1807(15) 1 calc R U P A 2
N2A N 0.2590(9) 0.5520(6) 0.6825(6) 0.0130(9) Uani 0.1807(15) 1 d . . P A 2
H2A3 H 0.2744 0.6206 0.7542 0.016 Uiso 0.1807(15) 1 calc R U P A 2
N3A N 0.2442(12) 0.4950(8) 0.4338(8) 0.0166(2) Uani 0.1807(15) 1 d . . P A 2
C5A C 0.2682(12) 0.5921(9) 0.5454(9) 0.0133(2) Uani 0.1807(15) 1 d . . P A 2
C1A C 0.2265 0.4087 0.7109 0.0122(2) Uani 0.1807(15) 1 d . . P A 2
C4A C 0.1712 0.2159 0.9003 0.035(2) Uani 0.1807(15) 1 d . . P A 2
H4A1 H 0.2194 0.1931 0.9954 0.042 Uiso 0.1807(15) 1 calc R U P A 2
H4A2 H 0.0260 0.1788 0.8801 0.042 Uiso 0.1807(15) 1 calc R U P A 2
C3A C 0.2628 0.1393 0.7945 0.0281(16) Uani 0.1807(15) 1 d . . P A 2
H3A1 H 0.2605 0.0387 0.8111 0.034 Uiso 0.1807(15) 1 calc R U P A 2
H3A2 H 0.4006 0.1892 0.7922 0.034 Uiso 0.1807(15) 1 calc R U P A 2
C2A C 0.1055 0.1490 0.6436 0.0302(7) Uani 0.1807(15) 1 d . . P A 2
H2A1 H 0.1101 0.0756 0.5641 0.036 Uiso 0.1807(15) 1 calc R U P A 2
H2A2 H -0.0329 0.1427 0.6602 0.036 Uiso 0.1807(15) 1 calc R U P A 2
O2W O 0.1312(2) 0.16372(13) 0.30218(13) 0.0279(2) Uani 1 1 d D . . . .
C9 C 0.3148(2) 0.75703(15) 0.53955(15) 0.0207(2) Uani 1 1 d . . . . .
H9 H 0.3338 0.8377 0.6104 0.025 Uiso 1 1 calc R U . A 1
C7 C 0.2896(2) 0.66540(17) 0.29550(15) 0.0209(2) Uani 1 1 d . . . . .
H7 H 0.2915 0.6793 0.1990 0.025 Uiso 1 1 calc R U . . .
C8 C 0.3204(2) 0.78267(15) 0.40085(15) 0.0198(2) Uani 1 1 d . . . . .
H8 H 0.3447 0.8780 0.3780 0.024 Uiso 1 1 calc R U . . .
C6 C 0.2562(2) 0.52799(16) 0.33341(16) 0.0218(2) Uani 1 1 d . . . . .
H6 H 0.2339 0.4455 0.2643 0.026 Uiso 1 1 calc R U . A 1
H4W H 0.220(3) 0.123(3) 0.251(2) 0.069(11) Uiso 1 1 d D . . . .
H3W H 0.027(3) 0.174(4) 0.231(2) 0.065(10) Uiso 1 1 d D . . . .
H1W H 0.499(3) 0.096(3) 0.138(3) 0.062(10) Uiso 1 1 d D . . . .
H2W H 0.336(4) -0.037(2) 0.0890(17) 0.056(9) Uiso 1 1 d 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'
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'
S S 0.1246 0.1234 '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'
O O 0.0106 0.0060 '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
C1 S1 C4 101.63(7) . .
C4A S1A C1A 94.3(2) . .
C1 N1 C2 124.4(3) . .
C1 N2 C5 127.29(14) . .
C9 N3 C5 117.80(14) . .
N1 C1 N2 122.04(14) . .
N1 C1 S1 125.48(11) . .
N2 C1 S1 112.48(12) . .
C3 C4 S1 112.24(10) . .
C2 C3 C4 110.0(3) . .
N1 C2 C3 118.4(5) . .
N3 C5 N2 118.39(14) . .
N3 C5 C6 122.87(14) . .
N2 C5 C6 118.74(15) . .
C1A N1A C2A 122.9(5) . .
C1A N2A C5A 123.8(5) . .
C6 N3A C5A 119.5(7) . .
N3A C5A N2A 121.1(7) . .
N3A C5A C9 123.8(6) . .
N2A C5A C9 115.1(6) . .
N3A C5A C6 26.6(4) . .
N2A C5A C6 147.7(6) . .
C9 C5A C6 97.2(4) . .
N1A C1A N2A 124.7(4) . .
N1A C1A S1A 128.4(3) . .
N2A C1A S1A 106.8(3) . .
C3A C4A S1A 115.2(2) . .
C4A C3A C2A 99.3 . .
N1A C2A C3A 96.6(3) . .
N3 C9 C8 124.46(14) . .
C8 C9 C5A 109.7(3) . .
C6 C7 C8 119.03(12) . .
C9 C8 C7 118.40(12) . .
N3A C6 C7 129.5(4) . .
C7 C6 C5 117.42(13) . .
N3A C6 C5A 33.9(5) . .
C7 C6 C5A 95.6(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.7435(16) .
S1 C4 1.8059(16) .
S1A C4A 1.857(5) .
S1A C1A 1.873(6) .
N1 C1 1.302(2) .
N1 C2 1.396(7) .
N2 C1 1.3547(19) .
N2 C5 1.401(2) .
N3 C9 1.322(2) .
N3 C5 1.328(2) .
C4 C3 1.516(2) .
C3 C2 1.493(7) .
C5 C6 1.434(2) .
N1A C1A 1.229(8) .
N1A C2A 1.558(7) .
N2A C1A 1.408(5) .
N2A C5A 1.415(9) .
N3A C6 1.054(8) .
N3A C5A 1.312(12) .
C5A C9 1.558(9) .
C5A C6 2.047(8) .
C4A C3A 1.4760 .
C3A C2A 1.7147 .
C9 C8 1.3824(19) .
C7 C6 1.387(2) .
C7 C8 1.392(2) .
