#------------------------------------------------------------------------------
#$Date: 2024-10-06 09:57:42 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/23/1572361.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_1572361
loop_
_publ_author_name
'Kaya, Busra'
'Smith, Henry'
'Chen, Yanbing'
'Azad, Mahan Gholam'
'M Russell, Tiffany'
'Richardson, Vera'
'Bernhardt, Paul V.'
'Dharmasivam, Mahendiran'
'Richardson, Des R.'
_publ_section_title
;
 Targeting lysosomes by design: novel N-acridine thiosemicarbazones
 that enable direct detection of intracellular drug localization and
 overcome P-glycoprotein (Pgp)-mediated resistance.
;
_journal_issue                   37
_journal_name_full               'Chemical science'
_journal_page_first              15109
_journal_page_last               15124
_journal_paper_doi               10.1039/d4sc04339a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_sum            'C20 H16 N6 S'
_chemical_formula_weight         372.45
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_date             2022-07-20T14:11:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2024-05-14 deposited with the CCDC.	2024-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                109.261(5)
_cell_angle_beta                 101.174(4)
_cell_angle_gamma                101.954(4)
_cell_formula_units_Z            2
_cell_length_a                   8.8060(5)
_cell_length_b                   9.4077(5)
_cell_length_c                   11.8916(6)
_cell_measurement_reflns_used    3929
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      61.42
_cell_measurement_theta_min      4.11
_cell_measurement_wavelength     1.54184
_cell_volume                     872.43(9)
_computing_cell_refinement       'CrysalisPro (Agilent Technologies,     )'
_computing_data_collection       'CrysalisPro (Agilent Technologies,     )'
_computing_data_reduction        'CrysalisPro (Agilent Technologies,     )'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      190(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.02
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type
'Agilent Technologies Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.049425
_diffrn_orient_matrix_UB_12      0.150071
_diffrn_orient_matrix_UB_13      -0.026463
_diffrn_orient_matrix_UB_21      -0.153574
_diffrn_orient_matrix_UB_22      0.040734
_diffrn_orient_matrix_UB_23      0.02632
_diffrn_orient_matrix_UB_31      0.093546
_diffrn_orient_matrix_UB_32      0.093427
_diffrn_orient_matrix_UB_33      0.138164
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5869
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_reduction_process
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        61.596
_diffrn_reflns_theta_max         61.596
_diffrn_reflns_theta_min         4.107
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.792
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0775P)²+0.1919P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0
_reflns_number_gt                2490
_reflns_number_total             2684
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc04339a2.cif
_cod_data_source_block           2248aoap2
_cod_depositor_comments
'Adding full bibliography for 1572360--1572364.cif.'
_cod_database_code               1572361
_shelx_estimated_absorpt_t_min   0.534
_shelx_estimated_absorpt_t_max   0.775
_shelx_shelxl_version_number     2018/1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C -0.1597(2) -0.0363(2) 0.11528(16) 0.0273(4) Uani 1 1 d . . . . .
C2 C -0.0586(2) -0.0369(2) 0.22096(18) 0.0327(5) Uani 1 1 d . . . . .
H2 H 0.032686 0.052118 0.269228 0.039 Uiso 1 1 calc R U . . .
N6 N -0.0852(2) -0.1574(2) 0.25669(17) 0.0432(5) Uani 1 1 d . . . . .
C3 C -0.2152(3) -0.2786(3) 0.1855(2) 0.0447(5) Uani 1 1 d . . . . .
H3 H -0.23829 -0.368001 0.20681 0.054 Uiso 1 1 calc R U . . .
C4 C -0.3166(3) -0.2785(2) 0.0823(2) 0.0454(6) Uani 1 1 d . . . . .
H4 H -0.408483 -0.367449 0.035319 0.054 Uiso 1 1 calc R U . . .
C5 C -0.1301(2) 0.0957(2) 0.07272(16) 0.0264(4) Uani 1 1 d . . . . .
C6 C -0.2438(3) 0.0827(3) -0.0434(2) 0.0463(6) Uani 1 1 d . . . . .
H6A H -0.309222 0.154833 -0.022296 0.069 Uiso 1 1 calc R U . . .
H6B H -0.315029 -0.025526 -0.086986 0.069 Uiso 1 1 calc R U . . .
H6C H -0.181878 0.110397 -0.097188 0.069 Uiso 1 1 calc R U . . .
C7 C 0.1647(2) 0.4624(2) 0.17702(16) 0.0247(4) Uani 1 1 d . . . . .
C8 C 0.3912(2) 0.5638(2) 0.36535(15) 0.0220(4) Uani 1 1 d . . . . .
C9 C 0.5347(2) 0.5238(2) 0.36026(16) 0.0239(4) Uani 1 1 d . . . . .
C10 C 0.5424(2) 0.3846(2) 0.26851(17) 0.0288(4) Uani 1 1 d . . . . .
H10 H 0.446395 0.313081 0.207024 0.035 Uiso 1 1 calc R U . . .
C11 C 0.6865(3) 0.3535(3) 0.26855(19) 0.0362(5) Uani 1 1 d . . . . .
H11 H 0.690221 0.259985 0.207489 0.043 Uiso 1 1 calc R U . . .
C12 C 0.8309(3) 0.4593(3) 0.3587(2) 0.0380(5) Uani 1 1 d . . . . .
H12 H 0.930695 0.436141 0.357137 0.046 Uiso 1 1 calc R U . . .
C13 C 0.8291(2) 0.5934(2) 0.44734(18) 0.0327(4) Uani 1 1 d . . . . .
H13 H 0.927469 0.663273 0.506828 0.039 Uiso 1 1 calc R U . . .
C14 C 0.6806(2) 0.6303(2) 0.45195(16) 0.0257(4) Uani 1 1 d . . . . .
C15 C 0.5460(2) 0.8029(2) 0.54229(16) 0.0253(4) Uani 1 1 d . . . . .
C16 C 0.5519(2) 0.9495(2) 0.63330(17) 0.0334(5) Uani 1 1 d . . . . .
H16 H 0.651842 1.015204 0.692788 0.04 Uiso 1 1 calc R U . . .
C17 C 0.4165(3) 0.9957(2) 0.63566(18) 0.0374(5) Uani 1 1 d . . . . .
H17 H 0.422642 1.093256 0.697229 0.045 Uiso 1 1 calc R U . . .
C18 C 0.2656(3) 0.9007(2) 0.54767(19) 0.0363(5) Uani 1 1 d . . . . .
H18 H 0.17217 0.935903 0.550024 0.044 Uiso 1 1 calc R U . . .
C19 C 0.2538(2) 0.7595(2) 0.45992(18) 0.0292(4) Uani 1 1 d . . . . .
H19 H 0.151939 0.696249 0.40201 0.035 Uiso 1 1 calc R U . . .
C20 C 0.3930(2) 0.7058(2) 0.45413(16) 0.0243(4) Uani 1 1 d . . . . .
N1 N -0.2915(2) -0.15863(19) 0.04533(16) 0.0387(4) Uani 1 1 d . . . . .
N2 N -0.00479(17) 0.21362(17) 0.14064(13) 0.0253(4) Uani 1 1 d . . . . .
N3 N 0.03026(18) 0.33884(17) 0.10552(14) 0.0279(4) Uani 1 1 d . . . . .
H3A H -0.032417 0.339511 0.038485 0.034 Uiso 1 1 calc R U . . .
N4 N 0.24224(17) 0.45277(17) 0.28176(13) 0.0238(3) Uani 1 1 d . . . . .
H4A H 0.198865 0.373318 0.300151 0.029 Uiso 1 1 calc R U . . .
N5 N 0.68545(18) 0.76423(18) 0.54286(14) 0.0287(4) Uani 1 1 d . . . . .
S1 S 0.22485(6) 0.61118(5) 0.13373(4) 0.0352(2) 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
N1 C1 C2 120.77(17) . . ?
N1 C1 C5 116.03(16) . . ?
C2 C1 C5 123.20(16) . . ?
N6 C2 C1 122.48(18) . . ?
C2 N6 C3 115.99(18) . . ?
N6 C3 C4 122.08(19) . . ?
N1 C4 C3 122.61(19) . . ?
N2 C5 C1 115.94(16) . . ?
N2 C5 C6 125.21(17) . . ?
C1 C5 C6 118.85(15) . . ?
N4 C7 N3 114.89(15) . . ?
N4 C7 S1 123.84(13) . . ?
N3 C7 S1 121.27(13) . . ?
C20 C8 C9 120.63(15) . . ?
C20 C8 N4 120.94(15) . . ?
C9 C8 N4 118.36(15) . . ?
C8 C9 C10 123.49(16) . . ?
C8 C9 C14 117.46(16) . . ?
C10 C9 C14 119.04(16) . . ?
C11 C10 C9 120.37(18) . . ?
C10 C11 C12 120.59(19) . . ?
C13 C12 C11 120.97(18) . . ?
C12 C13 C14 120.53(18) . . ?
N5 C14 C13 118.09(16) . . ?
N5 C14 C9 123.42(16) . . ?
C13 C14 C9 118.50(17) . . ?
N5 C15 C16 118.11(16) . . ?
N5 C15 C20 123.56(16) . . ?
C16 C15 C20 118.32(17) . . ?
C17 C16 C15 120.69(18) . . ?
C16 C17 C18 121.04(18) . . ?
C19 C18 C17 120.36(19) . . ?
C18 C19 C20 120.57(17) . . ?
C8 C20 C19 123.88(16) . . ?
C8 C20 C15 117.10(16) . . ?
C19 C20 C15 119.01(16) . . ?
C4 N1 C1 116.05(17) . . ?
C5 N2 N3 118.78(15) . . ?
C7 N3 N2 118.42(14) . . ?
C7 N4 C8 123.91(14) . . ?
C14 N5 C15 117.68(15) . . ?
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
C1 N1 1.344(2) . ?
C1 C2 1.395(3) . ?
C1 C5 1.482(2) . ?
C2 N6 1.329(3) . ?
N6 C3 1.332(3) . ?
C3 C4 1.371(3) . ?
C4 N1 1.333(3) . ?
C5 N2 1.287(2) . ?
C5 C6 1.492(3) . ?
C7 N4 1.340(2) . ?
C7 N3 1.365(2) . ?
C7 S1 1.6672(18) . ?
C8 C20 1.397(3) . ?
C8 C9 1.398(3) . ?
C8 N4 1.429(2) . ?
C9 C10 1.426(3) . ?
C9 C14 1.431(3) . ?
C10 C11 1.359(3) . ?
C11 C12 1.414(3) . ?
C12 C13 1.357(3) . ?
C13 C14 1.427(3) . ?
C14 N5 1.349(2) . ?
C15 N5 1.350(2) . ?
C15 C16 1.428(3) . ?
C15 C20 1.435(3) . ?
C16 C17 1.353(3) . ?
C17 C18 1.418(3) . ?
C18 C19 1.360(3) . ?
C19 C20 1.424(3) . ?
N2 N3 1.372(2) . ?
