New anthrahydrazone derivatives and their cisplatin-like complexes: Synthesis, antitumor activity and structure-activity relationship
Liu, Rui-Xue; Wu, Ying-Shu; Liu, Yan-Cheng; Luo, Ru-Yi; Yang, Li-Dong; Tang, Meng-Ting; Chen, Zhen-Feng; Liang, Hong; New Journal of Chemistry 43 (2019) 18685–18694; doi:10.1039/C9NJ02965F

data_7058961
_publ_section_title
;
 New anthrahydrazone derivatives and their cisplatin-like complexes:
 Synthesis, antitumor activity and structure-activity relationship
;
_journal_issue                   47
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              18685
_journal_page_last               18694
_journal_paper_doi               10.1039/C9NJ02965F
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C19 H14 Cl2 N4 Pt, C2 H6 O S'
_chemical_formula_sum            'C21 H20 Cl2 N4 O Pt S'
_chemical_formula_weight         642.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-05-28
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2019-06-06 deposited with the CCDC.	2019-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                102.199(3)
_cell_angle_beta                 103.963(3)
_cell_angle_gamma                98.146(3)
_cell_formula_units_Z            2
_cell_length_a                   9.1092(3)
_cell_length_b                   9.8959(4)
_cell_length_c                   13.2673(5)
_cell_measurement_reflns_used    5802
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4580
_cell_measurement_theta_min      3.4640
_cell_volume                     1110.77(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_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 0.998
_diffrn_measurement_details
;
  1 omega  -95.00  -35.00   1.0000    2.5250
omega____ theta____ kappa____ phi______ frames
    -      -18.7075 -178.0000   60.0000 60

  2 omega  -40.00   50.00   1.0000    2.5250
omega____ theta____ kappa____ phi______ frames
    -      -18.7075   57.0000    0.0000 90

  3 omega  -11.00   89.00   1.0000    2.5250
omega____ theta____ kappa____ phi______ frames
    -       19.0200   77.0000   90.0000 100

  4 omega  -20.00   61.00   1.0000    2.5250
omega____ theta____ kappa____ phi______ frames
    -       19.0200  -99.0000 -180.0000 81

  5 omega  -11.00   89.00   1.0000    2.5250
omega____ theta____ kappa____ phi______ frames
    -       19.0200   77.0000   60.0000 100

  6 omega   -2.00   88.00   1.0000    2.5250
omega____ theta____ kappa____ phi______ frames
    -       19.0200   57.0000  -30.0000 90

  7 omega   -2.00   88.00   1.0000    2.5250
omega____ theta____ kappa____ phi______ frames
    -       19.0200   57.0000 -120.0000 90

  8 omega  -95.00  -63.00   1.0000    2.5250
omega____ theta____ kappa____ phi______ frames
    -      -18.7075 -178.0000  150.0000 32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0297190000
_diffrn_orient_matrix_UB_12      0.0423509000
_diffrn_orient_matrix_UB_13      0.0372970000
_diffrn_orient_matrix_UB_21      -0.0006669000
_diffrn_orient_matrix_UB_22      -0.0526036000
_diffrn_orient_matrix_UB_23      0.0289261000
_diffrn_orient_matrix_UB_31      0.0763527000
_diffrn_orient_matrix_UB_32      0.0323428000
_diffrn_orient_matrix_UB_33      0.0319104000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1181
_diffrn_reflns_av_unetI/netI     0.0964
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13462
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.339
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    6.672
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.921
_exptl_crystal_description       block
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_refine_diff_density_max         2.564
_refine_diff_density_min         -1.557
_refine_diff_density_rms         0.206
_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     273
_refine_ls_number_reflns         4556
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0489
_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/[\s^2^(Fo^2^)+(0.0514P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1285
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3955
_reflns_number_total             4556
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj02965f2.cif
_cod_data_source_block           lrx-298pt
_cod_original_cell_volume        1110.76(8)
_cod_database_code               7058961
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.502
_shelx_estimated_absorpt_t_min   0.171
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C1(H1), C2(H2), C3(H3a), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11),
 C13(H13), C15(H15), C16(H16), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C20(H20a,H20b,H20c), C21(H21a,H21b,H21c)
;
_olex2_submission_special_instructions 'No special instructions were received'