#------------------------------------------------------------------------------
#$Date: 2023-05-05 05:11:43 +0300 (Fri, 05 May 2023) $
#$Revision: 283293 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/18/7711882.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_7711882
loop_
_publ_author_name
'Jiang, Ming'
'Zhang, Juzheng'
'Xu, Shihang'
'Li, Yanping'
'Li, Wenjuan'
'Liang, Hong'
'Yang, Feng'
_publ_section_title
;
 Designing a multitarget In(III) compound to overcome the resistance of
 lung cancer cells to cisplatin.
;
_journal_issue                   2
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              269
_journal_page_last               280
_journal_paper_doi               10.1039/d2dt03374g
_journal_volume                  52
_journal_year                    2023
_chemical_formula_moiety         'C12 H15 Cl2 In N4 S'
_chemical_formula_sum            'C12 H15 Cl2 In N4 S'
_chemical_formula_weight         433.06
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-11-09
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-13 deposited with the CCDC.	2022-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.635(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5919(4)
_cell_length_b                   12.4526(6)
_cell_length_c                   15.0859(10)
_cell_measurement_reflns_used    1234
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.0340
_cell_measurement_theta_min      3.9580
_cell_volume                     1613.96(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00  50.00   1.00    7.50    --  -19.80  77.00 -90.00  100
  2  ω    -50.00  50.00   1.00    7.50    --  -19.80  77.00   0.00  100
  3  ω    -90.00 -65.00   1.00    7.50    --  -19.80 -77.00 -90.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0214759000
_diffrn_orient_matrix_UB_12      -0.0413377000
_diffrn_orient_matrix_UB_13      0.0298197000
_diffrn_orient_matrix_UB_21      -0.0137368000
_diffrn_orient_matrix_UB_22      0.0389054000
_diffrn_orient_matrix_UB_23      0.0333295000
_diffrn_orient_matrix_UB_31      -0.0785079000
_diffrn_orient_matrix_UB_32      0.0045223000
_diffrn_orient_matrix_UB_33      -0.0145898000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.1019
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6556
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         3.540
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.919
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.782
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
_exptl_crystal_preparation       'heated 343 k'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.639
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.867
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3150
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.867
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0430
_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)+(0.0053P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0515
_refine_ls_wR_factor_ref         0.0605
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1916
_reflns_number_total             3150
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt03374g2.cif
_cod_data_source_block           c4
_cod_depositor_comments
'Adding full bibliography for 7711878--7711882.cif.'
_cod_original_cell_volume        1613.95(15)
_cod_database_code               7711882
_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   0.788
_shelx_estimated_absorpt_t_min   0.667
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C0AA(H0AA,H0AB), C1AA(H1AA,H1AB), C5(H5A,H5B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C10(H10), C19(H19)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.302
_oxdiff_exptl_absorpt_empirical_full_min 0.896
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
In1 In 0.35765(4) 0.40168(3) 0.14392(3) 0.03590(12) Uani 1 1 d . . . . .
S2 S 0.19308(15) 0.52962(11) 0.05844(10) 0.0410(4) Uani 1 1 d . . . . .
Cl3 Cl 0.26724(16) 0.22959(11) 0.09914(11) 0.0567(5) Uani 1 1 d . . . . .
Cl5 Cl 0.28172(16) 0.42426(12) 0.29469(10) 0.0558(4) Uani 1 1 d . . . . .
C2 C 0.8606(5) 0.3992(5) 0.2120(4) 0.0459(16) Uani 1 1 d . . . . .
H2 H 0.934572 0.453566 0.215729 0.055 Uiso 1 1 calc R U . . .
C3 C 0.7125(5) 0.4216(4) 0.1810(3) 0.0317(13) Uani 1 1 d . . . . .
N4 N 0.5224(4) 0.5376(3) 0.1223(3) 0.0349(12) Uani 1 1 d . . . . .
C7 C 0.6388(6) 0.2444(4) 0.2038(4) 0.0450(16) Uani 1 1 d . . . . .
H7 H 0.562195 0.191632 0.201797 0.054 Uiso 1 1 calc R U . . .
N8 N 0.6030(4) 0.3439(3) 0.1780(3) 0.0355(12) Uani 1 1 d . . . . .
C9 C 0.6642(6) 0.5293(4) 0.1499(4) 0.0348(14) Uani 1 1 d . . . . .
C10 C 0.7862(6) 0.2176(4) 0.2333(4) 0.0494(17) Uani 1 1 d . . . . .
H10 H 0.809156 0.147522 0.250246 0.059 Uiso 1 1 calc R U . . .
N12 N 0.4722(5) 0.6353(3) 0.0923(3) 0.0417(13) Uani 1 1 d . . . . .
C15 C 0.3240(6) 0.6378(4) 0.0653(4) 0.0348(14) Uani 1 1 d . . . . .
C19 C 0.8988(6) 0.2959(5) 0.2374(4) 0.0520(17) Uani 1 1 d . . . . .
H19 H 0.999120 0.279582 0.256912 0.062 Uiso 1 1 calc R U . . .
C21 C 0.7751(5) 0.6211(4) 0.1516(4) 0.0482(17) Uani 1 1 d . . . . .
H21A H 0.800789 0.638880 0.211943 0.072 Uiso 1 1 calc R U . . .
H21B H 0.727986 0.682094 0.123125 0.072 Uiso 1 1 calc R U . . .
H21C H 0.868160 0.601588 0.120830 0.072 Uiso 1 1 calc R U . . .
C0AA C 0.1105(6) 0.7575(4) 0.0127(4) 0.0511(17) Uani 1 1 d . . . . .
H0AA H 0.037235 0.733471 0.056947 0.061 Uiso 1 1 calc R U . . .
H0AB H 0.085721 0.722941 -0.043325 0.061 Uiso 1 1 calc R U . . .
C1AA C 0.3650(6) 0.8313(4) 0.0478(4) 0.0507(17) Uani 1 1 d . . . . .
H1AA H 0.454535 0.827731 0.009247 0.061 Uiso 1 1 calc R U . . .
H1AB H 0.401036 0.842276 0.108254 0.061 Uiso 1 1 calc R U . . .
C5 C 0.2586(8) 0.9186(5) 0.0198(5) 0.091(3) Uani 1 1 d . . . . .
H5A H 0.254341 0.972929 0.065804 0.109 Uiso 1 1 calc R U . . .
H5B H 0.297311 0.952085 -0.033682 0.109 Uiso 1 1 calc R U . . .
C6 C 0.1069(7) 0.8768(5) 0.0036(6) 0.091(3) Uani 1 1 d . . . . .
H6A H 0.072140 0.896199 -0.055662 0.109 Uiso 1 1 calc R U . . .
H6B H 0.034426 0.906997 0.045679 0.109 Uiso 1 1 calc R U . . .
N0AA N 0.2721(5) 0.7338(3) 0.0407(3) 0.0404(12) 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
In In -0.7276 1.3100 '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'
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
Cl3 In1 S2 104.41(5) . . ?
Cl3 In1 Cl5 106.56(6) . . ?
Cl5 In1 S2 105.01(5) . . ?
N4 In1 S2 78.24(11) . . ?
N4 In1 Cl3 148.03(12) . . ?
N4 In1 Cl5 103.30(12) . . ?
N4 In1 N8 71.70(15) . . ?
N8 In1 S2 147.08(11) . . ?
N8 In1 Cl3 94.48(11) . . ?
N8 In1 Cl5 94.82(12) . . ?
C15 S2 In1 95.80(19) . . ?
C3 C2 H2 120.1 . . ?
C3 C2 C19 119.9(5) . . ?
C19 C2 H2 120.1 . . ?
C2 C3 C9 123.1(5) . . ?
N8 C3 C2 120.4(5) . . ?
N8 C3 C9 116.5(4) . . ?
C9 N4 In1 119.4(4) . . ?
C9 N4 N12 118.2(4) . . ?
N12 N4 In1 121.7(3) . . ?
N8 C7 H7 119.1 . . ?
N8 C7 C10 121.8(5) . . ?
C10 C7 H7 119.1 . . ?
C3 N8 In1 115.1(3) . . ?
C7 N8 In1 124.6(4) . . ?
C7 N8 C3 119.9(4) . . ?
C3 C9 C21 120.9(4) . . ?
N4 C9 C3 115.9(4) . . ?
N4 C9 C21 123.2(5) . . ?
C7 C10 H10 120.4 . . ?
C19 C10 C7 119.1(5) . . ?
C19 C10 H10 120.4 . . ?
C15 N12 N4 114.8(4) . . ?
N12 C15 S2 127.5(4) . . ?
N0AA C15 S2 117.5(4) . . ?
N0AA C15 N12 115.1(5) . . ?
C2 C19 H19 120.6 . . ?
C10 C19 C2 118.9(5) . . ?
C10 C19 H19 120.6 . . ?
C9 C21 H21A 109.5 . . ?
C9 C21 H21B 109.5 . . ?
C9 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
H0AA C0AA H0AB 109.0 . . ?
C6 C0AA H0AA 110.9 . . ?
C6 C0AA H0AB 110.9 . . ?
N0AA C0AA H0AA 110.9 . . ?
N0AA C0AA H0AB 110.9 . . ?
N0AA C0AA C6 104.1(5) . . ?
H1AA C1AA H1AB 108.9 . . ?
C5 C1AA H1AA 110.8 . . ?
C5 C1AA H1AB 110.8 . . ?
N0AA C1AA H1AA 110.8 . . ?
N0AA C1AA H1AB 110.8 . . ?
N0AA C1AA C5 104.8(4) . . ?
C1AA C5 H5A 109.7 . . ?
C1AA C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 C1AA 110.0(5) . . ?
C6 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
C0AA C6 H6A 109.8 . . ?
C0AA C6 H6B 109.8 . . ?
C5 C6 C0AA 109.3(5) . . ?
C5 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
C15 N0AA C0AA 124.9(5) . . ?
C15 N0AA C1AA 123.2(4) . . ?
C1AA N0AA C0AA 111.6(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
In1 S2 2.4819(14) . ?
In1 Cl3 2.3749(14) . ?
In1 Cl5 2.3899(15) . ?
In1 N4 2.233(4) . ?
In1 N8 2.281(4) . ?
S2 C15 1.757(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(6) . ?
C2 C19 1.381(7) . ?
C3 N8 1.350(5) . ?
C3 C9 1.478(6) . ?
N4 C9 1.288(5) . ?
N4 N12 1.366(5) . ?
C7 H7 0.9300 . ?
C7 N8 1.334(6) . ?
C7 C10 1.379(6) . ?
C9 C21 1.489(6) . ?
C10 H10 0.9300 . ?
C10 C19 1.374(7) . ?
N12 C15 1.333(6) . ?
C15 N0AA 1.328(6) . ?
C19 H19 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C0AA H0AA 0.9700 . ?
C0AA H0AB 0.9700 . ?
C0AA C6 1.492(7) . ?
C0AA N0AA 1.476(6) . ?
C1AA H1AA 0.9700 . ?
C1AA H1AB 0.9700 . ?
C1AA C5 1.479(6) . ?
C1AA N0AA 1.457(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.423(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
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
In1 S2 C15 N12 12.0(5) . . . . ?
In1 S2 C15 N0AA -168.3(4) . . . . ?
In1 N4 C9 C3 9.8(7) . . . . ?
In1 N4 C9 C21 -169.9(4) . . . . ?
In1 N4 N12 C15 -9.3(6) . . . . ?
S2 C15 N0AA C0AA 3.5(8) . . . . ?
S2 C15 N0AA C1AA 176.3(4) . . . . ?
C2 C3 N8 In1 171.6(4) . . . . ?
C2 C3 N8 C7 -1.1(8) . . . . ?
C2 C3 C9 N4 179.5(5) . . . . ?
C2 C3 C9 C21 -0.7(8) . . . . ?
C3 C2 C19 C10 -1.7(9) . . . . ?
N4 N12 C15 S2 -3.8(8) . . . . ?
N4 N12 C15 N0AA 176.5(5) . . . . ?
C7 C10 C19 C2 0.2(10) . . . . ?
N8 C3 C9 N4 -0.6(8) . . . . ?
N8 C3 C9 C21 179.1(5) . . . . ?
N8 C7 C10 C19 0.9(10) . . . . ?
C9 C3 N8 In1 -8.3(6) . . . . ?
C9 C3 N8 C7 179.1(5) . . . . ?
C9 N4 N12 C15 -179.7(5) . . . . ?
C10 C7 N8 In1 -172.3(4) . . . . ?
C10 C7 N8 C3 -0.4(9) . . . . ?
N12 N4 C9 C3 -179.6(4) . . . . ?
N12 N4 C9 C21 0.6(8) . . . . ?
N12 C15 N0AA C0AA -176.7(5) . . . . ?
N12 C15 N0AA C1AA -3.9(8) . . . . ?
C19 C2 C3 N8 2.1(9) . . . . ?
C19 C2 C3 C9 -178.0(5) . . . . ?
C1AA C5 C6 C0AA -5.0(10) . . . . ?
C5 C1AA N0AA C15 -175.8(6) . . . . ?
C5 C1AA N0AA C0AA -2.2(7) . . . . ?
C6 C0AA N0AA C15 172.9(6) . . . . ?
C6 C0AA N0AA C1AA -0.7(7) . . . . ?
N0AA C0AA C6 C5 3.4(9) . . . . ?
N0AA C1AA C5 C6 4.4(9) . . . . ?
