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_7248387
_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         'C39 H28 N2 O3 S'
_chemical_formula_sum            'C39 H28 N2 O3 S'
_chemical_formula_weight         604.73
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_primary     direct
_audit_creation_date             2020-08-15
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled Nov  7 2012 10:34:12, GUI svn.r4372)
;
_audit_update_record
;
2024-01-16 deposited with the CCDC.	2024-04-05 downloaded from the CCDC.
;
_cell_angle_alpha                74.204(7)
_cell_angle_beta                 74.975(6)
_cell_angle_gamma                86.981(5)
_cell_formula_units_Z            2
_cell_length_a                   8.0458(5)
_cell_length_b                   13.1703(9)
_cell_length_c                   14.8309(13)
_cell_measurement_reflns_used    3099
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.0220
_cell_measurement_theta_min      3.1860
_cell_volume                     1460.2(2)
_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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_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 0.9753
_diffrn_measured_fraction_theta_max 0.9787
_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    -42.00  62.00   1.00    1.00    --   25.69 -57.00  60.00  104
  2  \w     17.00  99.00   1.00    1.00    --   25.69  57.00-150.00   82
  3  \w    -47.00  38.00   1.00    1.00    --   25.69 -57.00 -60.00   85
  4  \w     35.00 103.00   1.00   15.00    --   66.85  63.00  90.00   68
  5  \w     -6.00 100.00   1.00   15.00    --   66.85 -63.00-120.00  106
  6  \w     61.00 141.00   1.00   15.00    --   66.85 178.00-120.00   80
  7  \w    118.00 143.00   1.00   15.00    --   66.85  63.00  90.00   25
  8  \w    101.00 140.00   1.00   15.00    --   66.85 111.00 -60.00   39
  9  \w    105.00 150.00   1.00   15.00    --   66.85 111.00 150.00   45
 10  \w    -19.00 152.00   1.00   15.00    --   66.85   0.00  60.00  171
 11  \w     12.00 109.00   1.00   15.00    --   66.85-111.00-120.00   97
 12  \w     78.00 131.00   1.00   40.00    --  108.00  65.00 150.00   53
 13  \w     25.00 113.00   1.00   40.00    --  108.00-104.00  90.00   88
 14  \w    150.00 177.00   1.00   40.00    --  108.00  65.00 150.00   27
 15  \w    115.00 158.00   1.00   40.00    --  108.00  65.00  90.00   43
 16  \w     75.00 101.00   1.00   40.00    --  108.00-104.00-180.00   26
 17  \w     23.00  49.00   1.00   40.00    --  108.00-104.00-180.00   26
 18  \w    130.00 173.00   1.00   40.00    --  108.00 104.00  90.00   43
 19  \w     34.00  85.00   1.00   40.00    --  108.00 -89.00  30.00   51
 20  \w    118.00 163.00   1.00   40.00    --  108.00  43.00-120.00   45
 21  \w    106.00 132.00   1.00   40.00    --  108.00 -89.00  30.00   26
 22  \w     41.00 124.00   1.00   40.00    --  108.00 -65.00  90.00   83
 23  \w     74.00 173.00   1.00   40.00    --  108.00  54.00 120.00   99
 24  \w     76.00 102.00   1.00   40.00    --  108.00  43.00-120.00   26
 25  \w     88.00 165.00   1.00   40.00    --  108.00 138.00 120.00   77
 26  \w     96.00 170.00   1.00   40.00    --  108.00 138.00   0.00   74
 27  \w     86.00 159.00   1.00   40.00    --  108.00 138.00  30.00   73
 28  \w     79.00 168.00   1.00   40.00    --  108.00  65.00-180.00   89
 29  \w     87.00 123.00   1.00   40.00    --  108.00-130.00 -12.07   36
 30  \w     76.00 136.00   1.00   40.00    --  108.00  77.00-150.00   60
 31  \w    145.00 177.00   1.00   40.00    --  108.00  77.00-150.00   32
 32  \w     36.00  84.00   1.00   40.00    --  108.00-130.00 -12.07   48
;
_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      -0.1044435000
_diffrn_orient_matrix_UB_12      -0.0226884000
_diffrn_orient_matrix_UB_13      0.1065470000
_diffrn_orient_matrix_UB_21      0.1379035000
_diffrn_orient_matrix_UB_22      0.0591266000
_diffrn_orient_matrix_UB_23      0.0225020000
_diffrn_orient_matrix_UB_31      -0.0969165000
_diffrn_orient_matrix_UB_32      0.1037895000
_diffrn_orient_matrix_UB_33      -0.0245881000
_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  0.0602
_diffrn_reflns_av_unetI/netI     0.0789
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8600
_diffrn_reflns_theta_full        66.9150
_diffrn_reflns_theta_max         66.91
_diffrn_reflns_theta_min         4.05
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.336
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.692
_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    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             722.000
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.3956
_refine_diff_density_min         -0.4025
_refine_diff_density_rms         0.0948
_refine_ls_d_res_high            0.8380
_refine_ls_d_res_low             10.9020
_refine_ls_goodness_of_fit_ref   0.9788
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    52
_refine_ls_number_parameters     407
_refine_ls_number_reflns         4393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9788
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0554
_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^)+(0.0581P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1360
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                3374
_reflns_number_total             4393
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ce00105b2.cif
_cod_data_source_block           RDS_14_Rt_Cu
_cod_depositor_comments
'Adding full bibliography for 7248386--7248390.cif.'
_cod_original_cell_volume        1460.25(19)
_cod_database_code               7248387
_chemical_oxdiff_formula         'C78 H56 N4 O6 S2 '
_reflns_odcompleteness_completeness 97.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H13 of C13, H21 of C21, H23 of C23, H6 of C6, H7 of C7, H10 of C10, H31 of
  C31, H30 of C30, H34 of C34, H24 of C24, H29 of C29, H36 of C36, H35 of C35,
  H14 of C14, H11 of C11, H2 of C2, H20 of C20, H5 of C5, H16 of C16, H17 of
  C17, H19 of C19, H3 of C3
 At 1.5 times of:
  {H38a,H38b,H38c} of C38, {H39a,H39b,H39c} of C39
2.a Aromatic/amide H refined with riding coordinates:
 C36(H36), C29(H29), C24(H24), C34(H34), C30(H30), C31(H31), C10(H10), C7(H7),
 C6(H6), C23(H23), C21(H21), C13(H13), C35(H35), C14(H14), C11(H11), C2(H2),
 C20(H20), C5(H5), C16(H16), C17(H17), C19(H19), C3(H3)
2.b Idealised Me refined as rotating group:
 C38(H38a,H38b,H38c), C39(H39a,H39b,H39c)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.331
_oxdiff_exptl_absorpt_empirical_full_min 0.248