#------------------------------------------------------------------------------
#$Date: 2021-10-16 01:59:07 +0300 (Sat, 16 Oct 2021) $
#$Revision: 269973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/85/7708573.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_7708573
loop_
_publ_author_name
'Swaminathan, Srividya'
'Haribabu, Jebiti'
'Mohamed Kasim, Mohamed Subarkhan'
'dasararaju, gayathri'
'Balakrishnan, Nithya'
'Bhuvanesh, Nattamai'
'Echeverria, Cesar'
'Karvembu, R.'
_publ_section_title
;
 Impact of aliphatic acyl and aromatic thioamide substituents on the
 anticancer activity of Ru(II)-p-cymene complexes carrying acylthiourea
 ligands -- In vitro and in vivo studies
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D1DT02611A
_journal_year                    2021
_chemical_formula_moiety         'C16 H24 N2 O S'
_chemical_formula_sum            'C16 H24 N2 O S'
_chemical_formula_weight         292.43
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-09-18 deposited with the CCDC.	2021-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.9433(18)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   34.4780(13)
_cell_length_b                   5.2020(2)
_cell_length_c                   18.8610(9)
_cell_measurement_reflns_used    5959
_cell_measurement_temperature    300
_cell_measurement_theta_max      23.131
_cell_measurement_theta_min      2.364
_cell_volume                     3380.9(2)
_computing_cell_refinement
'SAINT V8.38 Bruker AXS Inc., Madison, WI, USA.'
_computing_data_collection       'APEX 3 (Bruker AXS)'
_computing_data_reduction
'SAINT V8.38 Bruker AXS Inc., Madison, WI, USA.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      300
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10181
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        23.227
_diffrn_reflns_theta_max         23.227
_diffrn_reflns_theta_min         2.161
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1007 before and 0.0532 after correction. The Ratio of minimum to maximum transmission is 0.8875. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.428
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.204
_refine_diff_density_max         0.101
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2410
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0349
_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)+(0.0367P)²+1.4937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0899
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1907
_reflns_number_total             2410
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt02611a2.cif
_cod_data_source_block           svncan
_cod_database_code               7708573
_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_max   0.962
_shelx_estimated_absorpt_t_min   0.923
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B),
 C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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'
'-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 0.45214(2) 0.58892(11) 0.42788(3) 0.0690(2) Uani 1 1 d . . . . .
O1 O 0.52242(4) -0.0280(3) 0.32043(7) 0.0722(4) Uani 1 1 d . . . . .
N1 N 0.45876(4) 0.2608(3) 0.32197(8) 0.0552(4) Uani 1 1 d . . . . .
H1 H 0.472663 0.153708 0.299127 0.066 Uiso 1 1 calc R . . . .
N2 N 0.50763(4) 0.2507(3) 0.40835(8) 0.0554(4) Uani 1 1 d . . . . .
H2 H 0.516641 0.314150 0.447662 0.067 Uiso 1 1 calc R . . . .
C1 C 0.42115(5) 0.3260(4) 0.29286(9) 0.0498(5) Uani 1 1 d . . . . .
C2 C 0.39033(6) 0.1748(4) 0.30919(11) 0.0681(6) Uani 1 1 d . . . . .
H2A H 0.393868 0.034413 0.339255 0.082 Uiso 1 1 calc R . . . .
C3 C 0.35401(6) 0.2313(5) 0.28088(13) 0.0826(7) Uani 1 1 d . . . . .
H3 H 0.333022 0.127786 0.291659 0.099 Uiso 1 1 calc R . . . .
C4 C 0.34856(7) 0.4372(5) 0.23732(12) 0.0774(7) Uani 1 1 d . . . . .
H4 H 0.323887 0.475854 0.218866 0.093 Uiso 1 1 calc R . . . .
C5 C 0.37933(7) 0.5861(4) 0.22088(12) 0.0776(7) Uani 1 1 d . . . . .
H5 H 0.375636 0.726592 0.190900 0.093 Uiso 1 1 calc R . . . .
C6 C 0.41608(6) 0.5311(4) 0.24825(11) 0.0664(6) Uani 1 1 d . . . . .
H6 H 0.437119 0.632467 0.236447 0.080 Uiso 1 1 calc R . . . .
C7 C 0.47323(5) 0.3567(3) 0.38217(9) 0.0499(5) Uani 1 1 d . . . . .
C8 C 0.52938(5) 0.0563(4) 0.37962(11) 0.0554(5) Uani 1 1 d . . . . .
C9 C 0.56251(5) -0.0335(4) 0.42658(10) 0.0596(5) Uani 1 1 d . . . . .
H9A H 0.571121 -0.200181 0.410249 0.071 Uiso 1 1 calc R . . . .
H9B H 0.553621 -0.054222 0.474483 0.071 Uiso 1 1 calc R . . . .
C10 C 0.59649(5) 0.1513(4) 0.42765(10) 0.0598(5) Uani 1 1 d . . . . .
H10A H 0.587215 0.322321 0.438616 0.072 Uiso 1 1 calc R . . . .
H10B H 0.607183 0.156926 0.380765 0.072 Uiso 1 1 calc R . . . .
C11 C 0.62840(6) 0.0783(4) 0.48117(12) 0.0697(6) Uani 1 1 d . . . . .
H11A H 0.616720 0.030053 0.525303 0.084 Uiso 1 1 calc R . . . .
H11B H 0.642018 -0.070808 0.463717 0.084 Uiso 1 1 calc R . . . .
C12 C 0.65735(6) 0.2906(4) 0.49587(13) 0.0778(7) Uani 1 1 d . . . . .
H12A H 0.670302 0.329662 0.452298 0.093 Uiso 1 1 calc R . . . .
H12B H 0.643373 0.443630 0.509587 0.093 Uiso 1 1 calc R . . . .
C13 C 0.68763(6) 0.2311(5) 0.55266(13) 0.0835(7) Uani 1 1 d . . . . .
H13A H 0.674638 0.180328 0.595281 0.100 Uiso 1 1 calc R . . . .
H13B H 0.702772 0.085297 0.537411 0.100 Uiso 1 1 calc R . . . .
C14 C 0.71478(7) 0.4477(5) 0.57086(14) 0.0876(7) Uani 1 1 d . . . . .
H14A H 0.699609 0.594409 0.585360 0.105 Uiso 1 1 calc R . . . .
H14B H 0.728092 0.496547 0.528420 0.105 Uiso 1 1 calc R . . . .
C15 C 0.74467(8) 0.3894(5) 0.62851(16) 0.1053(9) Uani 1 1 d . . . . .
H15A H 0.731421 0.335455 0.670554 0.126 Uiso 1 1 calc R . . . .
H15B H 0.760423 0.246245 0.613407 0.126 Uiso 1 1 calc R . . . .
C16 C 0.77073(10) 0.6081(6) 0.6477(2) 0.1443(14) Uani 1 1 d . . . . .
H16A H 0.784210 0.662384 0.606626 0.216 Uiso 1 1 calc GR . . . .
H16B H 0.789200 0.554673 0.684025 0.216 Uiso 1 1 calc GR . . . .
H16C H 0.755599 0.748309 0.664974 0.216 Uiso 1 1 calc GR . . . .
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
C1 N1 H1 118.3 . . ?
C7 N1 H1 118.3 . . ?
C7 N1 C1 123.37(15) . . ?
C7 N2 H2 115.8 . . ?
C8 N2 H2 115.8 . . ?
C8 N2 C7 128.48(16) . . ?
C2 C1 N1 118.58(17) . . ?
C2 C1 C6 120.31(18) . . ?
C6 C1 N1 121.09(18) . . ?
C1 C2 H2A 120.2 . . ?
C1 C2 C3 119.6(2) . . ?
C3 C2 H2A 120.2 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.7(2) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.2(2) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
N1 C7 S1 124.04(14) . . ?
N1 C7 N2 116.71(16) . . ?
N2 C7 S1 119.24(14) . . ?
O1 C8 N2 122.12(18) . . ?
O1 C8 C9 123.64(18) . . ?
N2 C8 C9 114.22(17) . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C8 C9 C10 112.60(16) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C9 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
C9 C10 C11 113.16(16) . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 C10 113.57(17) . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C11 C12 H12A 108.6 . . ?
C11 C12 H12B 108.6 . . ?
H12A C12 H12B 107.5 . . ?
C13 C12 C11 114.81(19) . . ?
C13 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
C12 C13 H13A 108.5 . . ?
C12 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C14 C13 C12 115.0(2) . . ?
C14 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
C13 C14 H14A 108.5 . . ?
C13 C14 H14B 108.5 . . ?
C13 C14 C15 115.0(2) . . ?
H14A C14 H14B 107.5 . . ?
C15 C14 H14A 108.5 . . ?
C15 C14 H14B 108.5 . . ?
C14 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 C14 114.6(2) . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 C7 1.6653(19) . ?
O1 C8 1.216(2) . ?
N1 H1 0.8600 . ?
N1 C1 1.432(2) . ?
N1 C7 1.322(2) . ?
N2 H2 0.8600 . ?
N2 C7 1.384(2) . ?
N2 C8 1.380(2) . ?
C1 C2 1.366(3) . ?
C1 C6 1.366(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.377(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.359(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.358(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(3) . ?
C6 H6 0.9300 . ?
C8 C9 1.496(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.515(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.516(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.508(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.503(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.497(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.503(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.487(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
_geom_hbond_publ_flag
N1 H1 O1 0.86 1.99 2.6605(19) 134.3 . yes
N1 H1 O1 0.86 2.46 3.164(2) 140.0 2_655 yes
N2 H2 S1 0.86 2.60 3.4453(15) 168.5 5_666 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
O1 C8 C9 C10 101.8(2) . . . . ?
N1 C1 C2 C3 -178.93(19) . . . . ?
N1 C1 C6 C5 179.48(18) . . . . ?
N2 C8 C9 C10 -76.4(2) . . . . ?
C1 N1 C7 S1 -7.0(3) . . . . ?
C1 N1 C7 N2 171.69(16) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C2 C1 C6 C5 1.1(3) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
C7 N1 C1 C2 -92.7(2) . . . . ?
C7 N1 C1 C6 88.9(2) . . . . ?
C7 N2 C8 O1 9.0(3) . . . . ?
C7 N2 C8 C9 -172.78(17) . . . . ?
C8 N2 C7 S1 179.09(15) . . . . ?
C8 N2 C7 N1 0.4(3) . . . . ?
C8 C9 C10 C11 173.53(17) . . . . ?
C9 C10 C11 C12 -165.69(18) . . . . ?
C10 C11 C12 C13 175.66(19) . . . . ?
C11 C12 C13 C14 -176.1(2) . . . . ?
C12 C13 C14 C15 179.1(2) . . . . ?
C13 C14 C15 C16 -178.2(3) . . . . ?
