New 8-hydroxy quinoline-polycyclic aromatic hydrocarbon (PAH) conjugates and their sulfonated derivatives: effects of sulfonation and PAH size on their structural, supramolecular and cytotoxic properties
Sehlangia, Suman; Dogra, Surbhi; Mondal, Prosenjit; Pradeep, Chullikkattil P.; CrystEngComm 26 (2024) 2361–2372; doi:10.1039/D4CE00105B

data_7248390
_publ_section_title
;
 New 8-hydroxy quinoline-polycyclic aromatic hydrocarbon (PAH) conjugates
 and their sulfonated derivatives: effects of sulfonation and PAH size on
 their structural, supramolecular and cytotoxic properties
;
_journal_issue                   18
_journal_name_full               CrystEngComm
_journal_page_first              2361
_journal_page_last               2372
_journal_paper_doi               10.1039/D4CE00105B
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C37 H28 N2 O3 S'
_chemical_formula_sum            'C37 H28 N2 O3 S'
_chemical_formula_weight         580.712
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     direct
_audit_creation_date             2021-04-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2024-01-16 deposited with the CCDC.	2024-04-05 downloaded from the CCDC.
;
_cell_angle_alpha                103.279(5)
_cell_angle_beta                 103.085(5)
_cell_angle_gamma                96.474(5)
_cell_formula_units_Z            2
_cell_length_a                   10.5913(7)
_cell_length_b                   11.8069(7)
_cell_length_c                   12.2854(7)
_cell_measurement_reflns_used    3361
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.7430
_cell_measurement_theta_min      3.8970
_cell_volume                     1434.23(16)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9886
_diffrn_measured_fraction_theta_max 0.9886
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -14.00  58.00   1.00    1.00    --   25.57  70.00 -52.00   72
  2  \w      8.00 109.00   1.00    1.00    --   25.57  77.00  30.00  101
  3  \w     89.00 132.00   1.00    2.00    --   66.78  61.00  60.00   43
  4  \w    108.00 146.00   1.00    2.00    --   66.78 111.00 120.00   38
  5  \w     98.00 178.00   1.00    7.50    --  108.00 138.00  90.00   80
  6  \w     76.00 149.00   1.00    2.00    --   66.78  77.00  90.00   73
  7  \w    116.00 176.00   1.00    7.50    --  108.00 -11.00 120.00   60
  8  \w    115.00 177.00   1.00    7.50    --  108.00 -21.00   0.00   62
  9  \w     99.00 153.00   1.00    7.50    --  108.00 -43.00 120.00   54
 10  \w     87.00 113.00   1.00    7.50    --  108.00-104.00 120.00   26
 11  \w     72.00 143.00   1.00    7.50    --  108.00 -89.00  30.00   71
 12  \w     57.00  97.00   1.00    1.00    --   25.57-178.00 -60.00   40
 13  \w     14.00 114.00   1.00    2.00    --   66.78-111.00 -60.00  100
 14  \w     59.00 136.00   1.00    7.50    --  108.00 -83.00-172.70   77
 15  \w     57.00 105.00   1.00    7.50    --  108.00 -98.00-173.17   48
 16  \w     31.00 146.00   1.00    7.50    --  108.00 -54.00-180.00  115
 17  \w     68.00 128.00   1.00    7.50    --  108.00  43.00  30.00   60
 18  \w     55.00 102.00   1.00    1.00    --   25.57  57.00 150.00   47
 19  \w     41.00  80.00   1.00    2.00    --   66.78  61.00  60.00   39
 20  \w     32.00  72.00   1.00    2.00    --   66.78  77.00  90.00   40
 21  \w     32.00 142.00   1.00    2.00    --   66.78  61.00 150.00  110
 22  \w     57.00 150.00   1.00    2.00    --   66.78 178.00 -30.00   93
 23  \w     34.00 144.00   1.00    2.00    --   66.78  45.00-150.00  110
 24  \w     33.00 143.00   1.00    7.50    --  108.00 -54.00   0.00  110
 25  \w     47.00  73.00   1.00    7.50    --  108.00-104.00 120.00   26
 26  \w     27.00 113.00   1.00    7.50    --  108.00-104.00  30.00   86
 27  \w     31.00  65.00   1.00    7.50    --  108.00 -89.00  30.00   34
 28  \w     31.00  77.00   1.00    7.50    --  108.00 -43.00 120.00   46
 29  \w     32.00 106.00   1.00    7.50    --  108.00 -11.00 120.00   74
 30  \w     23.00 107.00   1.00    7.50    --  108.00 -21.00   0.00   84
 31  \w     27.00  52.00   1.00    7.50    --  108.00 -83.00-172.70   25
 32  \w      9.00  52.00   1.00    1.00    --   25.57  57.00 150.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1115610000
_diffrn_orient_matrix_UB_12      -0.0615406000
_diffrn_orient_matrix_UB_13      0.0501539000
_diffrn_orient_matrix_UB_21      0.0659143000
_diffrn_orient_matrix_UB_22      0.1161139000
_diffrn_orient_matrix_UB_23      0.0928552000
_diffrn_orient_matrix_UB_31      -0.0787682000
_diffrn_orient_matrix_UB_32      -0.0355419000
_diffrn_orient_matrix_UB_33      0.0817032000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.9886
_diffrn_reflns_Laue_measured_fraction_max 0.9886
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8716
_diffrn_reflns_point_group_measured_fraction_full 0.9886
_diffrn_reflns_point_group_measured_fraction_max 0.9886
_diffrn_reflns_theta_full        66.8459
_diffrn_reflns_theta_max         66.85
_diffrn_reflns_theta_min         3.91
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.335
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             610.468
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.2341
_refine_diff_density_min         -0.3936
_refine_diff_density_rms         0.0509
_refine_ls_d_res_high            0.8385
_refine_ls_d_res_low             11.3164
_refine_ls_goodness_of_fit_ref   1.0575
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    52
_refine_ls_number_parameters     390
_refine_ls_number_reflns         5036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0575
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0567P)^2^+0.2048P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1172
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              13
_reflns_limit_k_min              -14
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                4152
_reflns_number_total             5036
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ce00105b2.cif
_cod_data_source_block           SY_278_Rt_Cu
_cod_depositor_comments
'Adding full bibliography for 7248386--7248390.cif.'
_cod_original_cell_volume        1434.23(17)
_cod_database_code               7248390
_chemical_oxdiff_formula         'C74  H56  N4  O6  S2  '
_reflns_odcompleteness_completeness 98.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C10(H10), C24(H24), C33(H33), C34(H34), C2(H2), C32(H32), C19(H19),
 C7(H7), C14(H14), C3(H3), C23(H23), C5(H5), C27(H27), C21(H21), C22(H22),
 C29(H29), C6(H6), C17(H17), C15(H15), C28(H28), C16(H16)
2.b Idealised Me refined as rotating group:
 C36(H36a,H36b,H36c), C37(H37a,H37b,H37c)
;
_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 1.302
_oxdiff_exptl_absorpt_empirical_full_min 0.823