#------------------------------------------------------------------------------
#$Date: 2023-05-05 05:11:43 +0300 (Fri, 05 May 2023) $
#$Revision: 283293 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/18/7711878.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_7711878
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         'C10 H15 Cl2 In N4 O S'
_chemical_formula_sum            'C10 H15 Cl2 In N4 O S'
_chemical_formula_weight         425.04
_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_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                 100.690(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1554(3)
_cell_length_b                   13.3631(5)
_cell_length_c                   16.2296(6)
_cell_measurement_reflns_used    3537
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.0250
_cell_measurement_theta_min      3.7910
_cell_volume                     1524.92(10)
_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    'ShelXS (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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  94.00   1.00    2.50    --   17.61 178.00-150.00   59
  2  ω     -4.00  86.00   1.00    2.50    --   17.61  57.00 -90.00   90
  3  ω    -20.00  60.00   1.00    2.50    --   17.61 -99.00-180.00   80
  4  ω    -92.00   6.00   1.00    2.50    --  -19.88 -38.00 -30.00   98
  5  ω    -40.00  23.00   1.00    2.50    --  -19.88  57.00 -30.00   63
;
_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      0.0019383000
_diffrn_orient_matrix_UB_12      0.0524277000
_diffrn_orient_matrix_UB_13      0.0068172000
_diffrn_orient_matrix_UB_21      0.0925536000
_diffrn_orient_matrix_UB_22      0.0022905000
_diffrn_orient_matrix_UB_23      -0.0097298000
_diffrn_orient_matrix_UB_31      -0.0400582000
_diffrn_orient_matrix_UB_32      0.0078490000
_diffrn_orient_matrix_UB_33      -0.0428748000
_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  0.0378
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10849
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         3.376
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.034
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59947
_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    1.851
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_preparation       'heated 343k'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2988
_refine_ls_number_restraints     267
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0296
_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)+(0.0255P)²+0.8532P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0656
_refine_ls_wR_factor_ref         0.0702
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2454
_reflns_number_total             2988
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt03374g2.cif
_cod_data_source_block           c1
_cod_depositor_comments
'Adding full bibliography for 7711878--7711882.cif.'
_cod_database_code               7711878
_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   0.792
_shelx_estimated_absorpt_t_min   0.675
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O1-H1
 0.85 with sigma of 0.01
 In1-H1
 2.893498 with sigma of 0.02
3. Rigid bond restraints
 C1, C0AA
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C0AA, C1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
C5 \\sim C4 \\sim C6 \\sim C2 \\sim C9 \\sim C3 \\sim C7 \\sim C8 \\sim C1
\\sim C0AA: within 7A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 7A
5.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C7(H7), C8(H8)
5.c X=CH2 refined with riding coordinates:
 N4(H4A,H4B)
5.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C0AA(H0AA,H0AB,H0AC)
;
_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 1.538
_oxdiff_exptl_absorpt_empirical_full_min 0.730
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
In1 In 0.41978(4) 0.28668(2) 0.70050(2) 0.02919(10) Uani 1 1 d D . . . .
Cl1 Cl 0.74526(14) 0.36174(7) 0.71220(6) 0.0403(2) Uani 1 1 d . . . . .
Cl2 Cl 0.34008(18) 0.35485(9) 0.82537(6) 0.0537(3) Uani 1 1 d . . . . .
S1 S 0.52335(16) 0.11226(7) 0.72850(6) 0.0373(2) Uani 1 1 d . . . . .
N2 N 0.4116(4) 0.2293(2) 0.56948(17) 0.0261(7) Uani 1 1 d . . . . .
N1 N 0.3146(4) 0.4120(2) 0.61077(18) 0.0325(7) Uani 1 1 d . . . . .
N3 N 0.4582(4) 0.1322(2) 0.55432(17) 0.0311(7) Uani 1 1 d . . . . .
N4 N 0.5636(5) -0.0155(2) 0.61306(19) 0.0468(10) Uani 1 1 d . . . . .
H4A H 0.560845 -0.038186 0.563255 0.056 Uiso 1 1 calc R U . . .
H4B H 0.599662 -0.053605 0.655759 0.056 Uiso 1 1 calc R U . . .
O1 O 0.0960(4) 0.2386(3) 0.6685(2) 0.0612(9) Uani 1 1 d D . . . .
H1 H 0.010(3) 0.274(3) 0.683(3) 0.092 Uiso 1 1 d D U . . .
C5 C 0.3099(5) 0.3922(3) 0.5283(2) 0.0307(8) Uani 1 1 d . U . . .
C4 C 0.3606(5) 0.2889(3) 0.5068(2) 0.0312(8) Uani 1 1 d . U . . .
C6 C 0.2597(6) 0.4675(3) 0.4695(2) 0.0371(9) Uani 1 1 d . U . . .
H6 H 0.254056 0.454392 0.412804 0.045 Uiso 1 1 calc R U . . .
C2 C 0.5123(5) 0.0781(3) 0.6240(2) 0.0328(8) Uani 1 1 d . U . . .
C9 C 0.2743(6) 0.5033(3) 0.6349(3) 0.0411(9) Uani 1 1 d . U . . .
H9 H 0.279343 0.515357 0.691691 0.049 Uiso 1 1 calc R U . . .
C3 C 0.3529(7) 0.2583(3) 0.4179(2) 0.0473(11) Uani 1 1 d . U . . .
H3A H 0.467876 0.223558 0.413042 0.071 Uiso 1 1 calc R U . . .
H3B H 0.340071 0.316637 0.382817 0.071 Uiso 1 1 calc R U . . .
H3C H 0.245912 0.214887 0.400559 0.071 Uiso 1 1 calc R U . . .
C7 C 0.2181(6) 0.5619(3) 0.4956(3) 0.0419(9) Uani 1 1 d . U . . .
H7 H 0.185062 0.612663 0.456353 0.050 Uiso 1 1 calc R U . . .
C8 C 0.2252(6) 0.5809(3) 0.5788(3) 0.0440(10) Uani 1 1 d . U . . .
H8 H 0.197874 0.644263 0.597141 0.053 Uiso 1 1 calc R U . . .
C1 C 0.0118(7) 0.1444(4) 0.6391(3) 0.0631(11) Uani 1 1 d . U . . .
H1A H 0.107068 0.092242 0.651748 0.076 Uiso 1 1 calc R U . . .
H1B H -0.089747 0.129123 0.669235 0.076 Uiso 1 1 calc R U . . .
C0AA C -0.0619(9) 0.1435(5) 0.5526(3) 0.0989(18) Uani 1 1 d . U . . .
H0AA H 0.035180 0.163706 0.522491 0.148 Uiso 1 1 calc R U . . .
H0AB H -0.167324 0.188964 0.540584 0.148 Uiso 1 1 calc R U . . .
H0AC H -0.104087 0.077125 0.535755 0.148 Uiso 1 1 calc R 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'
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'
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
Cl2 In1 Cl1 98.50(4) . . ?
Cl2 In1 S1 108.41(4) . . ?
S1 In1 Cl1 96.95(4) . . ?
N2 In1 Cl1 93.93(8) . . ?
N2 In1 Cl2 164.62(8) . . ?
N2 In1 S1 78.83(7) . . ?
N2 In1 N1 72.28(10) . . ?
N2 In1 O1 81.24(11) . . ?
N1 In1 Cl1 86.91(8) . . ?
N1 In1 Cl2 99.29(8) . . ?
N1 In1 S1 151.05(8) . . ?
N1 In1 O1 82.18(12) . . ?
O1 In1 Cl1 168.97(10) . . ?
O1 In1 Cl2 84.92(8) . . ?
O1 In1 S1 91.86(9) . . ?
C2 S1 In1 96.32(13) . . ?
N3 N2 In1 121.8(2) . . ?
C4 N2 In1 119.3(2) . . ?
C4 N2 N3 119.0(3) . . ?
C5 N1 In1 115.9(2) . . ?
C9 N1 In1 123.8(2) . . ?
C9 N1 C5 120.1(3) . . ?
C2 N3 N2 113.6(3) . . ?
H4A N4 H4B 120.0 . . ?
C2 N4 H4A 120.0 . . ?
C2 N4 H4B 120.0 . . ?
In1 O1 H1 121.5(19) . . ?
C1 O1 In1 130.0(3) . . ?
C1 O1 H1 107(2) . . ?
N1 C5 C4 116.7(3) . . ?
N1 C5 C6 119.5(3) . . ?
C6 C5 C4 123.7(3) . . ?
N2 C4 C5 115.7(3) . . ?
N2 C4 C3 123.3(3) . . ?
C5 C4 C3 121.0(3) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.6(4) . . ?
C7 C6 H6 120.2 . . ?
N3 C2 S1 129.4(3) . . ?
N4 C2 S1 114.4(3) . . ?
N4 C2 N3 116.1(3) . . ?
N1 C9 H9 118.7 . . ?
N1 C9 C8 122.5(4) . . ?
C8 C9 H9 118.7 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.2(4) . . ?
C8 C7 H7 119.9 . . ?
C9 C8 H8 121.0 . . ?
C7 C8 C9 118.0(4) . . ?
C7 C8 H8 121.0 . . ?
O1 C1 H1A 108.9 . . ?
O1 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
C0AA C1 O1 113.3(5) . . ?
C0AA C1 H1A 108.9 . . ?
C0AA C1 H1B 108.9 . . ?
C1 C0AA H0AA 109.5 . . ?
C1 C0AA H0AB 109.5 . . ?
C1 C0AA H0AC 109.5 . . ?
H0AA C0AA H0AB 109.5 . . ?
H0AA C0AA H0AC 109.5 . . ?
H0AB C0AA H0AC 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
In1 Cl1 2.5104(10) . ?
In1 Cl2 2.3856(10) . ?
In1 S1 2.4624(10) . ?
In1 N2 2.251(3) . ?
In1 N1 2.255(3) . ?
In1 O1 2.367(3) . ?
S1 C2 1.744(4) . ?
N2 N3 1.373(4) . ?
N2 C4 1.289(4) . ?
N1 C5 1.358(4) . ?
N1 C9 1.329(5) . ?
N3 C2 1.337(4) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 C2 1.326(5) . ?
O1 H1 0.844(10) . ?
O1 C1 1.438(5) . ?
C5 C4 1.486(5) . ?
C5 C6 1.388(5) . ?
C4 C3 1.491(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(5) . ?
C9 H9 0.9300 . ?
C9 C8 1.383(5) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C7 H7 0.9300 . ?
C7 C8 1.366(5) . ?
C8 H8 0.9300 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C0AA 1.405(7) . ?
C0AA H0AA 0.9600 . ?
C0AA H0AB 0.9600 . ?
C0AA H0AC 0.9600 . ?
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 S1 C2 N3 -1.8(4) . . . . ?
In1 S1 C2 N4 179.0(3) . . . . ?
In1 N2 N3 C2 -1.7(4) . . . . ?
In1 N2 C4 C5 -0.3(4) . . . . ?
In1 N2 C4 C3 179.3(3) . . . . ?
In1 N1 C5 C4 4.4(4) . . . . ?
In1 N1 C5 C6 -175.5(3) . . . . ?
In1 N1 C9 C8 174.5(3) . . . . ?
In1 O1 C1 C0AA -101.3(5) . . . . ?
N2 N3 C2 S1 2.5(5) . . . . ?
N2 N3 C2 N4 -178.3(3) . . . . ?
N1 C5 C4 N2 -2.7(5) . . . . ?
N1 C5 C4 C3 177.7(3) . . . . ?
N1 C5 C6 C7 1.1(6) . . . . ?
N1 C9 C8 C7 0.1(6) . . . . ?
N3 N2 C4 C5 179.2(3) . . . . ?
N3 N2 C4 C3 -1.3(5) . . . . ?
C5 N1 C9 C8 0.5(6) . . . . ?
C5 C6 C7 C8 -0.4(6) . . . . ?
C4 N2 N3 C2 178.8(3) . . . . ?
C4 C5 C6 C7 -178.8(4) . . . . ?
C6 C5 C4 N2 177.2(3) . . . . ?
C6 C5 C4 C3 -2.4(6) . . . . ?
C6 C7 C8 C9 -0.2(6) . . . . ?
C9 N1 C5 C4 178.8(3) . . . . ?
C9 N1 C5 C6 -1.1(5) . . . . ?
