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_7248386
_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         'C33 H26 N2 O3 S'
_chemical_formula_sum            'C33 H26 N2 O3 S'
_chemical_formula_weight         530.65
_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'
_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                90
_cell_angle_beta                 93.154(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4377(3)
_cell_length_b                   14.7657(4)
_cell_length_c                   23.7592(7)
_cell_measurement_reflns_used    3347
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.7950
_cell_measurement_theta_min      3.5230
_cell_volume                     2605.35(15)
_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 0.9843
_diffrn_measured_fraction_theta_max 0.9892
_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     -4.00  60.00   1.00    1.00    --   25.57  57.00 -30.00   64
  2  \w     62.00  94.00   1.00    1.00    --   25.57  57.00 -30.00   32
  3  \w     61.00 139.00   1.00    1.00    --   66.78  61.00 -30.00   78
  4  \w    100.00 146.00   1.00    1.00    --   66.78 111.00-120.00   46
  5  \w    113.00 178.00   1.00    2.00    --  108.00 138.00   0.00   65
  6  \w    119.00 162.00   1.00    2.00    --  108.00 138.00  60.00   43
  7  \w     87.00 112.00   1.00    2.00    --  108.00 138.00  60.00   25
  8  \w     75.00 160.00   1.00    2.00    --  108.00  65.00   0.00   85
  9  \w     78.00 142.00   1.00    1.00    --   66.78  61.00  60.00   64
 10  \w     75.00 165.00   1.00    2.00    --  108.00  54.00  60.00   90
 11  \w     76.00 175.00   1.00    2.00    --  108.00  65.00  30.00   99
 12  \w     64.00 108.00   1.00    2.00    --  108.00-104.00 150.00   44
 13  \w     65.00 126.00   1.00    2.00    --  108.00-135.00 158.00   61
 14  \w     84.00 112.00   1.00    1.00    --   66.78-111.00 -30.00   28
 15  \w     33.00 142.00   1.00    2.00    --  108.00 -65.00 -30.00  109
 16  \w     50.00 101.00   1.00    1.00    --   25.57  57.00  60.00   51
 17  \w     36.00  74.00   1.00    1.00    --   66.78  61.00  60.00   38
 18  \w      9.00  48.00   1.00    1.00    --   25.57  57.00  60.00   39
 19  \w     23.00  51.00   1.00    2.00    --  108.00-104.00 150.00   28
 20  \w     29.00  55.00   1.00    2.00    --  108.00-135.00 158.00   26
 21  \w     17.00  49.00   1.00    1.00    --   66.78-111.00 -30.00   32
 22  \w     12.00  85.00   1.00    1.00    --   66.78-111.00-120.00   73
;
_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      0.0368634000
_diffrn_orient_matrix_UB_12      -0.1023284000
_diffrn_orient_matrix_UB_13      0.0057799000
_diffrn_orient_matrix_UB_21      -0.1871393000
_diffrn_orient_matrix_UB_22      -0.0203102000
_diffrn_orient_matrix_UB_23      -0.0282397000
_diffrn_orient_matrix_UB_31      0.0815608000
_diffrn_orient_matrix_UB_32      -0.0003359000
_diffrn_orient_matrix_UB_33      -0.0582001000
_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  0.0194
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8875
_diffrn_reflns_theta_full        66.7792
_diffrn_reflns_theta_max         66.78
_diffrn_reflns_theta_min         3.53
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.414
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.397
_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    1.353
_exptl_crystal_description       block
_exptl_crystal_F_000             1268.000
_exptl_crystal_size_max          0.329
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.138
_refine_diff_density_max         0.2190
_refine_diff_density_min         -0.4061
_refine_diff_density_rms         0.0520
_refine_ls_d_res_high            0.8389
_refine_ls_d_res_low             12.5359
_refine_ls_goodness_of_fit_ref   1.0803
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0803
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0561P)^2^+0.6988P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1190
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              -7
_reflns_number_gt                3729
_reflns_number_total             4575
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ce00105b2.cif
_cod_data_source_block           RDS_09_Rt_Cu
_cod_depositor_comments
'Adding full bibliography for 7248386--7248390.cif.'
_cod_original_cell_volume        2605.36(14)
_cod_database_code               7248386
_chemical_oxdiff_formula         'C132 H104 N8 O12 S4 '
_reflns_odcompleteness_completeness 98.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H17 of C17, H16 of C16, H19 of C19, H20 of C20, H23 of C23, H25 of C25, H11
  of C11, H28 of C28, H14 of C14, H10 of C10, H30 of C30, H29 of C29, H2 of C2,
  H7 of C7, H24 of C24, H21 of C21, H3 of C3, H6 of C6, H5 of C5, H15 of C15
 At 1.5 times of:
  {H33a,H33b,H33c} of C33, {H32a,H32b,H32c} of C32
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C25(H25), C23(H23), C28(H28), C14(H14), C10(H10), C30(H30),
 C29(H29), C2(H2), C7(H7), C24(H24), C21(H21), C3(H3), C6(H6), C5(H5), C15(H15),
  C17(H17), C16(H16), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C33(H33a,H33b,H33c), C32(H32a,H32b,H32c)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.278
_oxdiff_exptl_absorpt_empirical_full_min 0.869