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_7248388
_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_absolute_configuration unk
_chemical_formula_moiety         'C21 H15 N O'
_chemical_formula_sum            'C21 H15 N O'
_chemical_formula_weight         297.359
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_Int_Tables_number      29
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.9480(6)
_cell_length_b                   6.6074(3)
_cell_length_c                   14.6479(6)
_cell_measurement_reflns_used    1149
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.4880
_cell_measurement_theta_min      2.7740
_cell_volume                     1543.52(11)
_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 0.9886
_diffrn_measured_fraction_theta_max 0.8884
_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    -50.00 -24.00   1.00   19.20    --   26.84 -57.00-120.00   26
  2  \w    -11.00  65.00   1.00   19.20    --   26.84 -57.00-120.00   76
  3  \w      4.00  58.00   1.00   19.20    --   26.84 -57.00   0.00   54
;
_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      -0.0834363000
_diffrn_orient_matrix_UB_12      -0.0278993000
_diffrn_orient_matrix_UB_13      -0.0003231000
_diffrn_orient_matrix_UB_21      0.0598607000
_diffrn_orient_matrix_UB_22      -0.0308976000
_diffrn_orient_matrix_UB_23      0.0220339000
_diffrn_orient_matrix_UB_31      -0.0310789000
_diffrn_orient_matrix_UB_32      0.0156084000
_diffrn_orient_matrix_UB_33      0.0431694000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.9886
_diffrn_reflns_Laue_measured_fraction_max 0.8884
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3419
_diffrn_reflns_point_group_measured_fraction_full 0.7362
_diffrn_reflns_point_group_measured_fraction_max 0.6452
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.55
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       orthorhombic
_exptl_crystal_F_000             624.268
_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.093
_refine_diff_density_max         0.1386
_refine_diff_density_min         -0.1544
_refine_diff_density_rms         0.0387
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -1(3)
_refine_ls_d_res_high            0.7499
_refine_ls_d_res_low             7.9740
_refine_ls_goodness_of_fit_ref   1.0901
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2471
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0901
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0308P)^2^+0.6229P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1198
_reflns_Friedel_coverage         0.382
_reflns_limit_h_max              20
_reflns_limit_h_min              -20
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              13
_reflns_limit_l_min              -18
_reflns_number_gt                2023
_reflns_number_total             2471
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ce00105b2.cif
_cod_data_source_block           RDS_11M_Rt_Mo
_cod_depositor_comments
'Adding full bibliography for 7248386--7248390.cif.'
_cod_original_sg_symbol_Hall     ' P 2c -2ac'
_cod_database_code               7248388
_chemical_oxdiff_formula         'c h n o Co'
_reflns_odcompleteness_completeness 98.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C2(H2), C10(H10), C11(H11), C3(H3), C15(H15), C13(H13), C14(H14), C7(H7),
 C20(H20), C5(H5), C6(H6), C19(H19), C17(H17), C18(H18)
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 1.171
_oxdiff_exptl_absorpt_empirical_full_min 0.909