#------------------------------------------------------------------------------
#$Date: 2024-10-06 09:57:42 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/23/1572363.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_1572363
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            'C27 H20 Cl3 N5 O4'
_chemical_formula_weight         584.83
_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   mixed
_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             2024-05-14T16:08:15-00:00
_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                102.548(5)
_cell_angle_beta                 98.148(4)
_cell_angle_gamma                103.294(5)
_cell_formula_units_Z            2
_cell_length_a                   7.6716(4)
_cell_length_b                   11.4509(7)
_cell_length_c                   15.5455(10)
_cell_measurement_reflns_used    2423
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      61.26
_cell_measurement_theta_min      4.09
_cell_measurement_wavelength     1.54184
_cell_volume                     1270.60(14)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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      -0.014391
_diffrn_orient_matrix_UB_12      0.031993
_diffrn_orient_matrix_UB_13      -0.091568
_diffrn_orient_matrix_UB_21      -0.046958
_diffrn_orient_matrix_UB_22      -0.139153
_diffrn_orient_matrix_UB_23      -0.048418
_diffrn_orient_matrix_UB_31      -0.204872
_diffrn_orient_matrix_UB_32      -0.010071
_diffrn_orient_matrix_UB_33      -0.00398
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0724
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9940
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_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        61.76
_diffrn_reflns_theta_max         61.76
_diffrn_reflns_theta_min         2.973
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.658
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            gold
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     375
_refine_ls_number_reflns         3925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0566
_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)+(0.0581P)²+0.5525P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1444
_reflns_Friedel_coverage         0
_reflns_number_gt                2979
_reflns_number_total             3925
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc04339a2.cif
_cod_data_source_block           2301feaobp_auto
_cod_depositor_comments
'Adding full bibliography for 1572360--1572364.cif.'
_cod_database_code               1572363
_shelx_estimated_absorpt_t_min   0.528
_shelx_estimated_absorpt_t_max   0.867
_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 0.4897(4) 0.7358(3) 0.1207(2) 0.0232(7) Uani 1 1 d . . . . .
C2 C 0.3415(4) 0.6919(3) 0.0471(2) 0.0278(7) Uani 1 1 d . . . . .
H2 H 0.363141 0.686967 -0.012107 0.033 Uiso 1 1 calc R U . . .
C3 C 0.1668(4) 0.6561(3) 0.0598(2) 0.0320(8) Uani 1 1 d . . . . .
H3 H 0.067692 0.625409 0.009515 0.038 Uiso 1 1 calc R U . . .
C4 C 0.1331(4) 0.6645(3) 0.1470(2) 0.0327(8) Uani 1 1 d . . . . .
H4 H 0.012165 0.636683 0.156035 0.039 Uiso 1 1 calc R U . . .
C5 C 0.2753(4) 0.7129(3) 0.2181(2) 0.0298(8) Uani 1 1 d . . . . .
H5 H 0.253172 0.721313 0.277413 0.036 Uiso 1 1 calc R U . . .
C6 C 0.6785(4) 0.7740(3) 0.1158(2) 0.0253(7) Uani 1 1 d . . . . .
C7 C 0.5943(4) 0.8112(3) 0.2833(2) 0.0249(7) Uani 1 1 d . . . . .
C8 C 0.7444(4) 0.7513(3) 0.0299(2) 0.0249(7) Uani 1 1 d . . . . .
C9 C 0.6708(5) 0.6433(3) -0.0394(2) 0.0330(8) Uani 1 1 d . . . . .
H9 H 0.57063 0.580955 -0.033726 0.04 Uiso 1 1 calc R U . . .
C10 C 0.7428(5) 0.6264(4) -0.1165(2) 0.0407(9) Uani 1 1 d . . . . .
H10 H 0.689156 0.553447 -0.164215 0.049 Uiso 1 1 calc R U . . .
C11 C 0.8910(5) 0.7139(4) -0.1249(3) 0.0441(10) Uani 1 1 d . . . . .
H11 H 0.941436 0.700755 -0.177433 0.053 Uiso 1 1 calc R U . . .
C12 C 0.9660(5) 0.8210(4) -0.0565(3) 0.0437(10) Uani 1 1 d . . . . .
H12 H 1.068478 0.881727 -0.06204 0.052 Uiso 1 1 calc R U . . .
C13 C 0.8930(5) 0.8407(4) 0.0200(2) 0.0352(8) Uani 1 1 d . . . . .
H13 H 0.944135 0.915559 0.066252 0.042 Uiso 1 1 calc R U . . .
C14 C 0.6628(4) 0.8789(3) 0.4401(2) 0.0279(8) Uani 1 1 d . . . . .
C15 C 0.7218(4) 0.8109(3) 0.4993(2) 0.0284(7) Uani 1 1 d . . . . .
C16 C 0.6685(5) 0.6800(3) 0.4774(3) 0.0376(9) Uani 1 1 d . . . . .
H16 H 0.586987 0.6345 0.422167 0.045 Uiso 1 1 calc R U . . .
C17 C 0.7332(5) 0.6184(4) 0.5350(3) 0.0440(9) Uani 1 1 d . . . . .
H17 H 0.695777 0.530134 0.519945 0.053 Uiso 1 1 calc R U . . .
C18 C 0.8552(5) 0.6845(4) 0.6169(3) 0.0466(10) Uani 1 1 d . . . . .
H18 H 0.899933 0.640243 0.6562 0.056 Uiso 1 1 calc R U . . .
C19 C 0.9098(5) 0.8111(4) 0.6405(2) 0.0381(9) Uani 1 1 d . . . . .
H19 H 0.991406 0.854873 0.696023 0.046 Uiso 1 1 calc R U . . .
C20 C 0.8442(4) 0.8765(3) 0.5818(2) 0.0292(8) Uani 1 1 d . . . . .
C21 C 0.8392(4) 1.0716(3) 0.5507(2) 0.0275(7) Uani 1 1 d . . . . .
C22 C 0.8997(4) 1.2025(3) 0.5780(2) 0.0325(8) Uani 1 1 d . . . . .
H22 H 0.985878 1.243024 0.632647 0.039 Uiso 1 1 calc R U . . .
C23 C 0.8346(5) 1.2704(4) 0.5260(3) 0.0383(9) Uani 1 1 d . . . . .
H23 H 0.875914 1.358499 0.544727 0.046 Uiso 1 1 calc R U . . .
C24 C 0.7057(5) 1.2116(4) 0.4442(3) 0.0398(9) Uani 1 1 d . . . . .
H24 H 0.659588 1.260217 0.40899 0.048 Uiso 1 1 calc R U . . .
C25 C 0.6484(5) 1.0855(4) 0.4163(2) 0.0349(8) Uani 1 1 d . . . . .
H25 H 0.562721 1.046745 0.361265 0.042 Uiso 1 1 calc R U . . .
C26 C 0.7142(4) 1.0102(3) 0.4680(2) 0.0296(8) Uani 1 1 d . . . . .
N1 N 0.4511(3) 0.7500(2) 0.20554(17) 0.0235(6) Uani 1 1 d . . . . .
N2 N 0.8051(3) 0.8345(3) 0.18880(18) 0.0284(6) Uani 1 1 d . . . . .
N3 N 0.7641(3) 0.8576(3) 0.27083(18) 0.0283(6) Uani 1 1 d . . . . .
N4 N 0.5462(4) 0.8146(3) 0.35983(18) 0.0333(7) Uani 1 1 d . . . . .
N5 N 0.9015(3) 1.0033(3) 0.60314(18) 0.0283(6) Uani 1 1 d . . . . .
H5A H 0.982507 1.04241 0.653124 0.034 Uiso 1 1 calc R U . . .
Cl1A Cl 0.75328(12) 0.47136(8) 0.24807(6) 0.0397(3) Uani 1 1 d . . . . .
O1 O 0.9393(4) 0.5163(3) 0.2931(2) 0.0765(10) Uani 1 1 d . . . . .
O2 O 0.6390(8) 0.4207(5) 0.3030(3) 0.0829(16) Uani 0.922(12) 1 d . . P A 1
O3 O 0.7381(5) 0.3763(5) 0.1696(2) 0.0680(17) Uani 0.922(12) 1 d . . P A 1
O4 O 0.6970(7) 0.5716(4) 0.2262(5) 0.0935(18) Uani 0.922(12) 1 d . . P A 1
O2' O 0.630(6) 0.544(5) 0.256(3) 0.049(13) Uiso 0.078(12) 1 d . . P A 2
O3' O 0.761(5) 0.457(5) 0.156(3) 0.046(13) Uiso 0.078(12) 1 d . . P A 2
O4' O 0.688(5) 0.374(4) 0.278(3) 0.043(12) Uiso 0.078(12) 1 d . . P A 2
C1B C 0.4568(6) 0.1230(4) 0.1699(4) 0.0574(12) Uani 1 1 d . . . . .
H1B1 H 0.556554 0.16593 0.223017 0.069 Uiso 0.581(6) 1 d R U P B .
H1B2 H 0.402248 0.185972 0.150775 0.069 Uiso 0.581(6) 1 d R U P . .
H1B3 H 0.409347 0.135382 0.110906 0.069 Uiso 0.419(6) 1 d R U P . .
H1B4 H 0.486837 0.203606 0.215622 0.069 Uiso 0.419(6) 1 d R U P . .
Cl1B Cl 0.28933(14) 0.01374(10) 0.19833(7) 0.0545(3) Uani 1 1 d . . . . .
Cl2B Cl 0.6472(3) 0.0741(2) 0.1653(2) 0.0683(11) Uani 0.581(6) 1 d . . P B 1
Cl2C Cl 0.5493(7) 0.0447(3) 0.0780(4) 0.106(2) Uani 0.419(6) 1 d . . P B 2
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'
Cl Cl 0.3639 0.7018 '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'
O O 0.0492 0.0322 '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 117.6(3) . . ?
N1 C1 C6 116.5(3) . . ?
C2 C1 C6 125.8(3) . . ?
C3 C2 C1 120.6(3) . . ?
C2 C3 C4 120.2(3) . . ?
C5 C4 C3 119.1(3) . . ?
C4 C5 N1 120.9(3) . . ?
N2 C6 C1 121.0(3) . . ?
N2 C6 C8 115.9(3) . . ?
C1 C6 C8 123.0(3) . . ?
N4 C7 N3 126.0(3) . . ?
N4 C7 N1 115.5(3) . . ?
N3 C7 N1 118.5(3) . . ?
C9 C8 C13 118.5(3) . . ?
C9 C8 C6 123.3(3) . . ?
C13 C8 C6 118.2(3) . . ?
C10 C9 C8 120.3(3) . . ?
C11 C10 C9 120.7(4) . . ?
C10 C11 C12 119.6(3) . . ?
C11 C12 C13 120.4(4) . . ?
C12 C13 C8 120.5(4) . . ?
N4 C14 C26 121.8(3) . . ?
N4 C14 C15 118.6(3) . . ?
C26 C14 C15 119.5(3) . . ?
C16 C15 C20 118.8(3) . . ?
C16 C15 C14 122.3(3) . . ?
C20 C15 C14 118.9(3) . . ?
C17 C16 C15 120.3(3) . . ?
C16 C17 C18 120.5(4) . . ?
C19 C18 C17 120.9(4) . . ?
C18 C19 C20 119.4(3) . . ?
N5 C20 C19 120.2(3) . . ?
N5 C20 C15 119.7(3) . . ?
C19 C20 C15 120.1(3) . . ?
N5 C21 C22 120.1(3) . . ?
N5 C21 C26 119.5(3) . . ?
C22 C21 C26 120.4(3) . . ?
C23 C22 C21 119.9(3) . . ?
C22 C23 C24 120.9(4) . . ?
C25 C24 C23 119.8(4) . . ?
C24 C25 C26 121.3(3) . . ?
C14 C26 C21 119.2(3) . . ?
C14 C26 C25 123.2(3) . . ?
C21 C26 C25 117.6(3) . . ?
C5 N1 C1 121.4(3) . . ?
C5 N1 C7 118.4(3) . . ?
C1 N1 C7 120.1(3) . . ?
C6 N2 N3 121.8(3) . . ?
N2 N3 C7 121.2(3) . . ?
C7 N4 C14 122.5(3) . . ?
C21 N5 C20 123.0(3) . . ?
O4' Cl1A O2' 107(3) . . ?
O4 Cl1A O3 111.1(3) . . ?
O4' Cl1A O3' 120(3) . . ?
O2' Cl1A O3' 100(2) . . ?
O4' Cl1A O1 104.2(16) . . ?
O2' Cl1A O1 122.4(19) . . ?
O4 Cl1A O1 107.9(3) . . ?
O3 Cl1A O1 108.8(2) . . ?
O3' Cl1A O1 104.1(15) . . ?
O4 Cl1A O2 108.9(3) . . ?
O3 Cl1A O2 108.3(3) . . ?
O1 Cl1A O2 111.8(3) . . ?
Cl2B C1B Cl1B 110.3(3) . . ?
Cl1B C1B Cl2C 109.8(3) . . ?
C1B Cl2C Cl2C 136.9(4) . 2_655 ?
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 1.376(4) . ?
C1 C2 1.404(4) . ?
C1 C6 1.431(5) . ?
C2 C3 1.365(5) . ?
C3 C4 1.402(5) . ?
C4 C5 1.354(5) . ?
C5 N1 1.373(4) . ?
C6 N2 1.322(4) . ?
C6 C8 1.485(5) . ?
C7 N4 1.290(4) . ?
C7 N3 1.347(4) . ?
C7 N1 1.435(4) . ?
C8 C9 1.391(5) . ?
C8 C13 1.397(5) . ?
C9 C10 1.385(5) . ?
C10 C11 1.374(6) . ?
C11 C12 1.379(6) . ?
C12 C13 1.383(5) . ?
C14 N4 1.372(4) . ?
C14 C26 1.414(5) . ?
C14 C15 1.419(5) . ?
C15 C16 1.409(5) . ?
C15 C20 1.417(5) . ?
C16 C17 1.363(6) . ?
C17 C18 1.410(6) . ?
C18 C19 1.363(6) . ?
C19 C20 1.410(5) . ?
C20 N5 1.366(5) . ?
C21 N5 1.358(4) . ?
C21 C22 1.410(5) . ?
C21 C26 1.419(5) . ?
C22 C23 1.358(5) . ?
C23 C24 1.420(6) . ?
C24 C25 1.360(6) . ?
C25 C26 1.424(5) . ?
N2 N3 1.342(4) . ?
Cl1A O4' 1.32(4) . ?
Cl1A O2' 1.40(4) . ?
Cl1A O4 1.405(4) . ?
Cl1A O3 1.418(3) . ?
Cl1A O3' 1.42(4) . ?
Cl1A O1 1.419(3) . ?
Cl1A O2 1.424(4) . ?
C1B Cl2B 1.685(5) . ?
C1B Cl1B 1.753(4) . ?
C1B Cl2C 1.836(6) . ?
Cl2C Cl2C 2.356(12) 2_655 ?
