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_7248389
_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         'C27 H17 N O'
_chemical_formula_sum            'C27 H17 N O'
_chemical_formula_weight         371.442
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_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                90
_cell_angle_beta                 107.494(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5838(15)
_cell_length_b                   6.6875(6)
_cell_length_c                   18.8389(19)
_cell_measurement_reflns_used    1539
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.3570
_cell_measurement_theta_min      4.9090
_cell_volume                     1872.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_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 0.9859
_diffrn_measured_fraction_theta_max 0.9859
_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     57.00 118.00   1.00    1.00    --   25.57 178.00  30.00   61
  2  \w    -16.00 108.00   1.00    1.00    --   25.57  77.00   0.00  124
  3  \w     35.00 133.00   1.00    3.50    --   66.78  61.00   0.00   98
  4  \w    103.00 148.00   1.00    3.50    --   66.78 111.00-180.00   45
  5  \w    -13.00  76.00   1.00    3.50    --   66.78 -45.00-150.00   89
  6  \w     75.00 148.00   1.00    3.50    --   66.78 178.00 120.00   73
  7  \w     77.00 147.00   1.00    3.50    --   66.78 178.00 -90.00   70
  8  \w     28.00  99.00   1.00   10.00    --  108.00-104.00-180.00   71
  9  \w    100.00 134.00   1.00   10.00    --  108.00 138.00-150.00   34
 10  \w     98.00 124.00   1.00   10.00    --  108.00 -57.00-165.00   26
 11  \w     45.00  71.00   1.00   10.00    --  108.00 -57.00-165.00   26
 12  \w    109.00 137.00   1.00   10.00    --  108.00 -65.00-120.00   28
 13  \w     95.00 177.00   1.00   10.00    --  108.00 138.00-120.00   82
 14  \w     24.00 110.00   1.00   10.00    --  108.00-104.00-120.00   86
 15  \w     25.00  56.00   1.00   10.00    --  108.00 -11.00 120.00   31
 16  \w     36.00 107.00   1.00   10.00    --  108.00 -65.00-120.00   71
 17  \w     84.00 111.00   1.00   10.00    --  108.00 -11.00 120.00   27
 18  \w    128.00 178.00   1.00   10.00    --  108.00 -11.00 120.00   50
 19  \w     68.00 165.00   1.00   10.00    --  108.00  54.00   0.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0701482000
_diffrn_orient_matrix_UB_12      0.0135281000
_diffrn_orient_matrix_UB_13      -0.0425751000
_diffrn_orient_matrix_UB_21      -0.0591406000
_diffrn_orient_matrix_UB_22      0.1546947000
_diffrn_orient_matrix_UB_23      -0.0533883000
_diffrn_orient_matrix_UB_31      0.0480949000
_diffrn_orient_matrix_UB_32      0.1703778000
_diffrn_orient_matrix_UB_33      0.0517941000
_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  0.0200
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.9859
_diffrn_reflns_Laue_measured_fraction_max 0.9859
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5854
_diffrn_reflns_point_group_measured_fraction_full 0.9859
_diffrn_reflns_point_group_measured_fraction_max 0.9859
_diffrn_reflns_theta_full        66.8890
_diffrn_reflns_theta_max         66.89
_diffrn_reflns_theta_min         4.92
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.623
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.566
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             778.300
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.111
_refine_diff_density_max         0.1510
_refine_diff_density_min         -0.1675
_refine_diff_density_rms         0.0393
_refine_ls_d_res_high            0.8382
_refine_ls_d_res_low             8.9838
_refine_ls_goodness_of_fit_ref   1.0493
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0493
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0647P)^2^+0.1382P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1357
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -18
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              -11
_reflns_number_gt                2325
_reflns_number_total             3275
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ce00105b2.cif
_cod_data_source_block           SY_Pyrene_Rt_Cu
_cod_depositor_comments
'Adding full bibliography for 7248386--7248390.cif.'
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               7248389
_chemical_oxdiff_formula         'C108  H68  N4  O4  '
_reflns_odcompleteness_completeness 98.14
_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 O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C2(H2), C13(H13), C24(H24), C23(H23), C3(H3), C14(H14),
 C21(H21), C19(H19), C20(H20), C17(H17), C5(H5), C16(H16), C6(H6), C7(H7)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 1.331
_oxdiff_exptl_absorpt_empirical_full_min 0.870