#------------------------------------------------------------------------------
#$Date: 2025-02-06 04:32:51 +0200 (Thu, 06 Feb 2025) $
#$Revision: 297620 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/99/7249907.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_7249907
loop_
_publ_author_name
'O'Sullivan, Patrick'
'Previtali, Viola'
'Twamley, Brendan'
'Marmion, Celine J.'
'McDonald, Aidan R.'
'Rozas, Isabel'
_publ_section_title
;
 Platinum(ii) complexes of aryl guanidine-like derivatives as potential
 anticancer agents: between coordination and cyclometallation.
;
_journal_issue                   5
_journal_name_full               'RSC advances'
_journal_page_first              3427
_journal_page_last               3438
_journal_paper_doi               10.1039/d5ra00310e
_journal_volume                  15
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C9 H14 Cl N3 O Pt S'
_chemical_formula_sum            'C9 H14 Cl N3 O Pt S'
_chemical_formula_weight         442.83
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-11-22
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-12-19 deposited with the CCDC.	2025-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6799(6)
_cell_length_b                   8.0262(4)
_cell_length_c                   13.2131(7)
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.09
_cell_measurement_theta_min      2.97
_cell_volume                     1238.66(11)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX 4 (Bruker, 2021)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL  (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.258
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0134
_diffrn_reflns_av_unetI/netI     0.0099
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21524
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.044
_diffrn_reflns_theta_min         2.969
_diffrn_source                   'standard sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_type              'Siemens, KFF Mo 2K -90 C'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    11.694
_exptl_absorpt_correction_T_max  0.2935
_exptl_absorpt_correction_T_min  0.2002
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0626 before and 0.0508 after correction.
The Ratio of minimum to maximum transmission is 0.5981.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1594 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.017(2)
_refine_ls_extinction_coef       0.00048(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         3560
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0091
_refine_ls_R_factor_gt           0.0086
_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)+(0.0070P)²+0.7294P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0187
_refine_ls_wR_factor_ref         0.0189
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                3481
_reflns_number_total             3560
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ra00310e2.cif
_cod_data_source_block           tcd152
_cod_database_code               7249907
_shelx_shelxl_version_number     2019/1
_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_max   0.388
_shelx_estimated_absorpt_t_min   0.227
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Me refined with riding coordinates:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), N7(H7), N10(H10)
2.c X=CH2 refined with riding coordinates:
 N9(H9A,H9B)
;
_olex2_exptl_crystal_mounting_method 'mounted in oil on a MiTeGen microloop'
_olex2_submission_original_sample_id pos464a
_olex2_submission_special_instructions 'No special instructions were received'
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'
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 0.4194(2) -0.0793(3) 0.48690(19) 0.0136(4) Uani 1 1 d . . . . .
C2 C 0.4259(2) -0.0315(3) 0.5897(2) 0.0176(5) Uani 1 1 d . . . . .
H2 H 0.371071 0.045659 0.614793 0.021 Uiso 1 1 calc R U . . .
C3 C 0.5083(3) -0.0917(3) 0.6559(2) 0.0200(5) Uani 1 1 d . . . . .
H3 H 0.510171 -0.054065 0.723997 0.024 Uiso 1 1 calc R U . . .
C4 C 0.5881(2) -0.2073(3) 0.6221(2) 0.0199(5) Uani 1 1 d . . . . .
H4 H 0.646956 -0.245637 0.665911 0.024 Uiso 1 1 calc R U . . .
C5 C 0.5806(2) -0.2659(3) 0.5238(2) 0.0163(5) Uani 1 1 d . . . . .
H5 H 0.633045 -0.348160 0.500789 0.020 Uiso 1 1 calc R U . . .
C6 C 0.4963(2) -0.2048(3) 0.45769(19) 0.0134(5) Uani 1 1 d . . . . .
C8 C 0.4093(2) -0.2809(3) 0.29302(19) 0.0138(5) Uani 1 1 d . . . . .
C11 C 0.4268(2) 0.3490(3) 0.4879(2) 0.0221(6) Uani 1 1 d . . . . .
H11A H 0.465549 0.350285 0.422119 0.033 Uiso 1 1 calc R U . . .
H11B H 0.418191 0.463416 0.512642 0.033 Uiso 1 1 calc R U . . .
H11C H 0.472470 0.284530 0.536297 0.033 Uiso 1 1 calc R U . . .
C12 C 0.2199(2) 0.4154(3) 0.4036(3) 0.0223(7) Uani 1 1 d . . . . .
H12A H 0.253271 0.420731 0.335613 0.033 Uiso 1 1 calc R U . . .
H12B H 0.137976 0.390563 0.398435 0.033 Uiso 1 1 calc R U . . .
H12C H 0.230416 0.522799 0.437678 0.033 Uiso 1 1 calc R U . . .
Cl1 Cl 0.15448(5) 0.09614(8) 0.27331(5) 0.01748(12) Uani 1 1 d . . . . .
N7 N 0.49649(18) -0.2785(3) 0.36062(16) 0.0149(4) Uani 1 1 d . . . . .
H7 H 0.560214 -0.328407 0.342044 0.018 Uiso 1 1 calc R U . . .
N9 N 0.4179(2) -0.3910(3) 0.21620(17) 0.0199(5) Uani 1 1 d . . . . .
H9A H 0.362548 -0.399099 0.171332 0.024 Uiso 1 1 calc R U . . .
H9B H 0.478956 -0.454807 0.210996 0.024 Uiso 1 1 calc R U . . .
N10 N 0.32001(19) -0.1844(3) 0.30301(17) 0.0148(4) Uani 1 1 d . . . . .
H10 H 0.259567 -0.211793 0.266909 0.018 Uiso 1 1 calc R U . . .
O1 O 0.23379(19) 0.2564(3) 0.57576(15) 0.0244(4) Uani 1 1 d . . . . .
Pt1 Pt 0.30348(2) 0.01822(2) 0.39021(2) 0.01078(3) Uani 1 1 d . . . . .
S1 S 0.28918(5) 0.25577(8) 0.47463(5) 0.01495(11) 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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pt Pt -1.7033 8.3905 '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 Pt1 122.60(19) . . ?
C6 C1 C2 115.1(2) . . ?
C6 C1 Pt1 122.21(18) . . ?
C1 C2 H2 118.4 . . ?
C3 C2 C1 123.2(3) . . ?
C3 C2 H2 118.4 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.1(3) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 121.9(2) . . ?
C1 C6 N7 123.5(2) . . ?
C5 C6 N7 114.6(2) . . ?
N9 C8 N7 116.7(2) . . ?
N10 C8 N7 121.7(2) . . ?
N10 C8 N9 121.6(2) . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
S1 C11 H11A 109.5 . . ?
S1 C11 H11B 109.5 . . ?
S1 C11 H11C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
S1 C12 H12A 109.5 . . ?
S1 C12 H12B 109.5 . . ?
S1 C12 H12C 109.5 . . ?
C6 N7 H7 116.4 . . ?
C8 N7 C6 127.1(2) . . ?
C8 N7 H7 116.4 . . ?
C8 N9 H9A 120.0 . . ?
C8 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
C8 N10 H10 116.0 . . ?
C8 N10 Pt1 128.08(18) . . ?
Pt1 N10 H10 116.0 . . ?
C1 Pt1 Cl1 172.07(7) . . ?
C1 Pt1 S1 93.76(7) . . ?
N10 Pt1 C1 89.13(10) . . ?
N10 Pt1 Cl1 84.92(7) . . ?
N10 Pt1 S1 174.88(7) . . ?
S1 Pt1 Cl1 92.57(2) . . ?
C11 S1 C12 99.18(13) . . ?
C11 S1 Pt1 110.05(10) . . ?
C12 S1 Pt1 112.82(12) . . ?
O1 S1 C11 107.64(14) . . ?
O1 S1 C12 105.88(15) . . ?
O1 S1 Pt1 119.28(9) . . ?
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 1.414(4) . ?
C1 C6 1.404(4) . ?
C1 Pt1 2.019(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.405(3) . ?
C6 N7 1.413(3) . ?
C8 N7 1.354(3) . ?
C8 N9 1.350(3) . ?
C8 N10 1.306(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 S1 1.782(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 S1 1.783(3) . ?
Cl1 Pt1 2.4095(6) . ?
N7 H7 0.8800 . ?
N9 H9A 0.8800 . ?
N9 H9B 0.8800 . ?
N10 H10 0.8800 . ?
N10 Pt1 2.002(2) . ?
O1 S1 1.485(2) . ?
Pt1 S1 2.2153(6) . ?
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
_geom_hbond_publ_flag
C11 H11A Cl1 0.98 2.99 3.912(3) 158 3 yes
N7 H7 Cl1 0.88 2.58 3.352(2) 147 3_545 yes
N9 H9A O1 0.88 2.10 2.826(3) 139 4_544 yes
N9 H9B Cl1 0.88 2.48 3.303(2) 155 3_545 yes
N10 H10 O1 0.88 2.54 3.104(3) 123 4_544 yes
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 C2 C3 C4 -1.4(4) . . . . ?
C1 C6 N7 C8 -20.7(4) . . . . ?
C2 C1 C6 C5 -6.0(4) . . . . ?
C2 C1 C6 N7 174.7(2) . . . . ?
C2 C3 C4 C5 -2.8(4) . . . . ?
C3 C4 C5 C6 2.4(4) . . . . ?
C4 C5 C6 C1 2.2(4) . . . . ?
C4 C5 C6 N7 -178.4(2) . . . . ?
C5 C6 N7 C8 159.9(3) . . . . ?
C6 C1 C2 C3 5.6(4) . . . . ?
N7 C8 N10 Pt1 16.4(4) . . . . ?
N9 C8 N7 C6 -164.4(2) . . . . ?
N9 C8 N10 Pt1 -165.37(19) . . . . ?
N10 C8 N7 C6 13.9(4) . . . . ?
Pt1 C1 C2 C3 -177.0(2) . . . . ?
Pt1 C1 C6 C5 176.61(19) . . . . ?
Pt1 C1 C6 N7 -2.8(3) . . . . ?
