#------------------------------------------------------------------------------
#$Date: 2020-12-19 05:06:01 +0200 (Sat, 19 Dec 2020) $
#$Revision: 259981 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/60/7706059.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_7706059
loop_
_publ_author_name
'Li, Shanhe'
'Khan, Muhammad Hamid'
'Wang, Xiaojun'
'Cai, Meiling'
'Zhang, Juzheng'
'Jiang, Ming'
'Zhang, Zhenlei'
'Wen, Xiao-An'
'Liang, Hong'
'Yang, Feng'
_publ_section_title
;
 Synthesis of a series of novel In(III) 2,6-diacetylpyridine
 bis(thiosemicarbazide) complexes: structure, anticancer function and
 mechanism.
;
_journal_issue                   47
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              17207
_journal_page_last               17220
_journal_paper_doi               10.1039/d0dt02266g
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C13 H18 Cl2 In N7 S2, C H4 O'
_chemical_formula_sum            'C14 H22 Cl2 In N7 O S2'
_chemical_formula_weight         554.22
_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   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-10-27 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.058(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.820(7)
_cell_length_b                   13.440(8)
_cell_length_c                   15.215(9)
_cell_measurement_reflns_used    5471
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.08
_cell_measurement_theta_min      2.44
_cell_volume                     2179(2)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19953
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.006
_diffrn_reflns_theta_max         25.006
_diffrn_reflns_theta_min         1.912
_exptl_absorpt_coefficient_mu    1.541
_exptl_absorpt_correction_T_max  0.857
_exptl_absorpt_correction_T_min  0.698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 1998)'
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.048
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3821
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0428
_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)+(0.0754P)²+3.3246P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1284
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3011
_reflns_number_total             3821
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt02266g2.cif
_cod_data_source_block           AAAA
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7706059
_shelx_shelxl_version_number     2014/7
_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   0.655
_shelx_estimated_absorpt_t_max   0.861
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 0.81590(3) 0.04978(3) 0.20538(2) 0.03398(16) Uani 1 1 d . U . . .
Cl1 Cl 1.02537(14) 0.02859(11) 0.14872(11) 0.0486(4) Uani 1 1 d . . . . .
S1 S 0.84995(16) -0.11299(11) 0.29464(10) 0.0474(4) Uani 1 1 d . . . . .
S2 S 0.94157(17) 0.11078(11) 0.36143(11) 0.0524(4) Uani 1 1 d . U . . .
Cl2 Cl 0.61003(14) 0.09467(12) 0.24577(10) 0.0503(4) Uani 1 1 d . . . . .
N6 N 0.8941(5) 0.2825(3) 0.2722(3) 0.0438(12) Uani 1 1 d . . . . .
H6 H 0.9541 0.3210 0.2573 0.053 Uiso 1 1 d R U . . .
N2 N 0.7168(4) -0.1730(3) 0.1320(3) 0.0383(11) Uani 1 1 d . . . . .
C5 C 0.6855(5) 0.0529(4) 0.0005(4) 0.0388(12) Uani 1 1 d . . . . .
C4 C 0.6787(5) -0.0525(4) 0.0245(4) 0.0396(13) Uani 1 1 d . . . . .
N7 N 0.9968(5) 0.2941(4) 0.4147(3) 0.0529(13) Uani 1 1 d . . . . .
H7 H 1.0520 0.3319 0.3930 0.063 Uiso 1 1 d R U . . .
C9 C 0.7440(5) 0.2141(4) 0.0483(4) 0.0413(13) Uani 1 1 d . . . . .
C12 C 0.9454(5) 0.2345(4) 0.3472(4) 0.0424(13) Uani 1 1 d . . . . .
C3 C 0.6221(6) -0.1282(5) -0.0429(4) 0.0568(17) Uani 1 1 d . . . . .
H3A H 0.5344 -0.1143 -0.0613 0.085 Uiso 1 1 calc R U . . .
H3B H 0.6321 -0.1934 -0.0168 0.085 Uiso 1 1 calc R U . . .
H3C H 0.6635 -0.1254 -0.0938 0.085 Uiso 1 1 calc R U . . .
N3 N 0.7237(4) -0.0751(3) 0.1075(3) 0.0373(10) Uani 1 1 d . . . . .
N5 N 0.8436(4) 0.2307(3) 0.1970(3) 0.0379(11) Uani 1 1 d . . . . .
C7 C 0.6398(7) 0.1889(5) -0.1018(4) 0.0597(18) Uani 1 1 d . . . . .
H7A H 0.6060 0.2135 -0.1580 0.072 Uiso 1 1 calc R U . . .
C6 C 0.6354(6) 0.0876(5) -0.0846(4) 0.0548(16) Uani 1 1 d . . . . .
H6A H 0.5996 0.0436 -0.1291 0.066 Uiso 1 1 calc R U . . .
C11 C 0.8056(7) 0.3893(5) 0.1130(5) 0.0605(18) Uani 1 1 d . . . . .
H11A H 0.8581 0.4053 0.0703 0.091 Uiso 1 1 calc R U . . .
H11B H 0.8386 0.4202 0.1692 0.091 Uiso 1 1 calc R U . . .
H11C H 0.7221 0.4134 0.0920 0.091 Uiso 1 1 calc R U . . .
C1 C 0.7034(7) -0.3673(5) 0.1810(5) 0.0655(19) Uani 1 1 d . . . . .
H1A H 0.7533 -0.3818 0.1362 0.098 Uiso 1 1 calc R U . . .
H1B H 0.6220 -0.3445 0.1527 0.098 Uiso 1 1 calc R U . . .
H1C H 0.6944 -0.4265 0.2147 0.098 Uiso 1 1 calc R U . . .
C8 C 0.6944(6) 0.2530(5) -0.0352(4) 0.0517(16) Uani 1 1 d . . . . .
H8 H 0.6980 0.3210 -0.0459 0.062 Uiso 1 1 calc R U . . .
C13 C 1.0622(7) 0.2575(6) 0.5004(4) 0.0636(18) Uani 1 1 d . . . . .
H13A H 1.1460 0.2382 0.4950 0.095 Uiso 1 1 calc R U . . .
H13B H 1.0183 0.2010 0.5183 0.095 Uiso 1 1 calc R U . . .
H13C H 1.0656 0.3091 0.5444 0.095 Uiso 1 1 calc R U . . .
C10 C 0.8023(5) 0.2781(4) 0.1250(4) 0.0410(13) Uani 1 1 d . . . . .
C2 C 0.7712(5) -0.1930(4) 0.2138(4) 0.0399(13) Uani 1 1 d . . . . .
N4 N 0.7394(4) 0.1155(3) 0.0647(3) 0.0368(10) Uani 1 1 d . . . . .
N1 N 0.7650(5) -0.2900(3) 0.2407(4) 0.0532(13) Uani 1 1 d . . . . .
H1E H 0.8439 -0.3100 0.2582 0.064 Uiso 1 1 d R U . . .
O1 O 0.4940(16) 0.3774(15) 0.1584(12) 0.289(10) Uani 1 1 d D . . . .
H1 H 0.4770 0.4252 0.1955 0.434 Uiso 1 1 d R U . . .
C14 C 0.430(2) 0.4212(17) 0.0768(11) 0.250(13) Uani 1 1 d D . . . .
H14A H 0.4520 0.4904 0.0755 0.375 Uiso 1 1 calc R U . . .
H14B H 0.3414 0.4146 0.0734 0.375 Uiso 1 1 calc R U . . .
H14C H 0.4555 0.3878 0.0270 0.375 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
N4 In1 N3 69.20(16) . . ?
N4 In1 N5 66.66(15) . . ?
N3 In1 N5 135.81(16) . . ?
N4 In1 Cl2 86.85(11) . . ?
N3 In1 Cl2 91.76(12) . . ?
N5 In1 Cl2 83.98(11) . . ?
N4 In1 S1 143.54(12) . . ?
N3 In1 S1 74.47(12) . . ?
N5 In1 S1 149.72(12) . . ?
Cl2 In1 S1 97.36(6) . . ?
N4 In1 Cl1 85.81(11) . . ?
N3 In1 Cl1 90.56(12) . . ?
N5 In1 Cl1 88.27(11) . . ?
Cl2 In1 Cl1 170.96(5) . . ?
S1 In1 Cl1 91.69(6) . . ?
N4 In1 S2 138.56(12) . . ?
N3 In1 S2 152.10(12) . . ?
N5 In1 S2 72.08(11) . . ?
Cl2 In1 S2 92.58(6) . . ?
S1 In1 S2 77.64(6) . . ?
Cl1 In1 S2 89.44(7) . . ?
C2 S1 In1 98.35(19) . . ?
C12 S2 In1 102.2(2) . . ?
C12 N6 N5 120.7(4) . . ?
C12 N6 H6 106.5 . . ?
N5 N6 H6 106.6 . . ?
C2 N2 N3 114.8(4) . . ?
N4 C5 C6 121.1(5) . . ?
N4 C5 C4 117.2(5) . . ?
C6 C5 C4 121.7(5) . . ?
N3 C4 C5 116.0(5) . . ?
N3 C4 C3 122.9(5) . . ?
C5 C4 C3 121.1(5) . . ?
C12 N7 C13 123.6(6) . . ?
C12 N7 H7 105.8 . . ?
C13 N7 H7 105.8 . . ?
N4 C9 C8 121.2(6) . . ?
N4 C9 C10 116.3(5) . . ?
C8 C9 C10 122.5(5) . . ?
N6 C12 N7 114.7(5) . . ?
N6 C12 S2 124.7(4) . . ?
N7 C12 S2 120.6(5) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 N3 N2 117.2(4) . . ?
C4 N3 In1 119.5(4) . . ?
N2 N3 In1 123.3(3) . . ?
C10 N5 N6 119.4(5) . . ?
C10 N5 In1 120.7(4) . . ?
N6 N5 In1 119.7(3) . . ?
C8 C7 C6 119.8(6) . . ?
C8 C7 H7A 120.1 . . ?
C6 C7 H7A 120.1 . . ?
C7 C6 C5 118.8(6) . . ?
C7 C6 H6A 120.6 . . ?
C5 C6 H6A 120.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C8 C9 118.8(6) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
N7 C13 H13A 109.5 . . ?
N7 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N7 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N5 C10 C9 114.7(5) . . ?
N5 C10 C11 125.9(6) . . ?
C9 C10 C11 119.4(5) . . ?
N2 C2 N1 116.3(5) . . ?
N2 C2 S1 128.9(4) . . ?
N1 C2 S1 114.8(4) . . ?
C5 N4 C9 120.3(5) . . ?
C5 N4 In1 118.1(3) . . ?
C9 N4 In1 121.6(4) . . ?
C2 N1 C1 122.0(6) . . ?
C2 N1 H1E 106.3 . . ?
C1 N1 H1E 106.3 . . ?
C14 O1 H1 97.5 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 N4 2.330(5) . ?
In1 N3 2.348(5) . ?
In1 N5 2.455(5) . ?
In1 Cl2 2.486(2) . ?
In1 S1 2.5673(19) . ?
In1 Cl1 2.578(2) . ?
In1 S2 2.652(2) . ?
S1 C2 1.741(6) . ?
S2 C12 1.678(6) . ?
N6 C12 1.344(7) . ?
N6 N5 1.369(6) . ?
N6 H6 0.8900 . ?
N2 C2 1.307(7) . ?
N2 N3 1.374(6) . ?
C5 N4 1.343(7) . ?
C5 C6 1.393(8) . ?
C5 C4 1.468(8) . ?
C4 N3 1.307(7) . ?
C4 C3 1.497(8) . ?
N7 C12 1.344(7) . ?
N7 C13 1.456(8) . ?
N7 H7 0.8900 . ?
C9 N4 1.351(7) . ?
C9 C8 1.392(8) . ?
C9 C10 1.498(8) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
N5 C10 1.278(7) . ?
C7 C8 1.383(10) . ?
C7 C6 1.389(10) . ?
C7 H7A 0.9300 . ?
C6 H6A 0.9300 . ?
C11 C10 1.507(8) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C1 N1 1.463(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C8 H8 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C2 N1 1.372(7) . ?
N1 H1E 0.8900 . ?
O1 C14 1.436(10) . ?
O1 H1 0.8948 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
N6 H6 S1 0.89 2.55 3.415(5) 164.8 2_755
N7 H7 Cl1 0.89 2.81 3.292(6) 115.3 2_755
N7 H7 N2 0.89 2.60 3.327(7) 140.0 2_755
C3 H3A Cl2 0.96 2.98 3.651(7) 128.5 3_655
C13 H13C Cl1 0.96 2.78 3.719(8) 167.3 4_566
N1 H1E Cl1 0.89 2.83 3.548(5) 138.6 2_745
O1 H1 Cl2 0.89 2.68 3.535(18) 160.7 2_655
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
N4 C5 C4 N3 1.4(8) . . . . ?
C6 C5 C4 N3 -176.8(5) . . . . ?
N4 C5 C4 C3 -179.1(5) . . . . ?
C6 C5 C4 C3 2.6(9) . . . . ?
N5 N6 C12 N7 177.0(5) . . . . ?
N5 N6 C12 S2 -6.2(8) . . . . ?
C13 N7 C12 N6 -177.1(5) . . . . ?
C13 N7 C12 S2 6.0(8) . . . . ?
In1 S2 C12 N6 0.0(5) . . . . ?
In1 S2 C12 N7 176.6(4) . . . . ?
C5 C4 N3 N2 179.1(4) . . . . ?
C3 C4 N3 N2 -0.4(8) . . . . ?
C5 C4 N3 In1 -2.5(7) . . . . ?
C3 C4 N3 In1 178.1(4) . . . . ?
C2 N2 N3 C4 175.2(5) . . . . ?
C2 N2 N3 In1 -3.1(6) . . . . ?
C12 N6 N5 C10 -175.8(5) . . . . ?
C12 N6 N5 In1 9.7(6) . . . . ?
C8 C7 C6 C5 0.6(10) . . . . ?
N4 C5 C6 C7 -1.2(9) . . . . ?
C4 C5 C6 C7 177.0(6) . . . . ?
C6 C7 C8 C9 -0.1(10) . . . . ?
N4 C9 C8 C7 0.0(9) . . . . ?
C10 C9 C8 C7 -178.5(6) . . . . ?
N6 N5 C10 C9 -177.4(4) . . . . ?
In1 N5 C10 C9 -3.0(6) . . . . ?
N6 N5 C10 C11 1.2(9) . . . . ?
In1 N5 C10 C11 175.7(5) . . . . ?
N4 C9 C10 N5 1.5(7) . . . . ?
C8 C9 C10 N5 -179.9(5) . . . . ?
N4 C9 C10 C11 -177.2(5) . . . . ?
C8 C9 C10 C11 1.3(9) . . . . ?
N3 N2 C2 N1 179.4(5) . . . . ?
N3 N2 C2 S1 0.2(8) . . . . ?
In1 S1 C2 N2 2.2(6) . . . . ?
In1 S1 C2 N1 -177.0(4) . . . . ?
C6 C5 N4 C9 1.1(8) . . . . ?
C4 C5 N4 C9 -177.2(5) . . . . ?
C6 C5 N4 In1 178.6(4) . . . . ?
C4 C5 N4 In1 0.3(6) . . . . ?
C8 C9 N4 C5 -0.5(8) . . . . ?
C10 C9 N4 C5 178.1(5) . . . . ?
C8 C9 N4 In1 -177.9(4) . . . . ?
C10 C9 N4 In1 0.7(6) . . . . ?
N2 C2 N1 C1 1.3(9) . . . . ?
S1 C2 N1 C1 -179.4(5) . . . . ?
