#------------------------------------------------------------------------------
#$Date: 2024-07-05 18:34:17 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/83/7248388.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7248388
loop_
_publ_author_name
'Sehlangia, Suman'
'Dogra, Surbhi'
'Mondal, Prosenjit'
'Pradeep, Chullikkattil P.'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00 -24.00   1.00   19.20    --   26.84 -57.00-120.00   26
  2  ω    -11.00  65.00   1.00   19.20    --   26.84 -57.00-120.00   76
  3  ω      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       'ω 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/[σ²(Fo²)+(0.0308P)²+0.6229P] where P=(Fo²+2Fc²)/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
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,z+1/2
3 -x+1/2,y,z+1/2
4 x+1/2,-y,z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
O1 O 0.85447(17) 0.6397(4) 0.74667(18) 0.0685(8) Uani 1.000000 .
H1 H 0.822(2) 0.720(3) 0.7229(19) 0.1028(12) Uiso 1.000000 GR
N1 N 0.75386(15) 0.6143(4) 0.60162(18) 0.0418(6) Uani 1.000000 .
C12 C 0.53275(18) 0.9749(5) 0.4431(2) 0.0400(7) Uani 1.000000 .
C9 C 0.80534(18) 0.4539(5) 0.6176(2) 0.0395(7) Uani 1.000000 .
C4 C 0.80897(18) 0.2795(5) 0.5625(2) 0.0399(7) Uani 1.000000 .
C8 C 0.8574(2) 0.4659(5) 0.6961(2) 0.0491(8) Uani 1.000000 .
C2 C 0.70805(18) 0.4440(5) 0.4664(2) 0.0431(7) Uani 1.000000 .
H2 H 0.67545(18) 0.4460(5) 0.4137(2) 0.0517(9) Uiso 1.000000 R
C1 C 0.70487(18) 0.6096(5) 0.5280(2) 0.0405(7) Uani 1.000000 .
C10 C 0.6472(2) 0.7795(5) 0.5178(2) 0.0500(9) Uani 1.000000 .
H10 H 0.6497(2) 0.8794(5) 0.5625(2) 0.0600(10) Uiso 1.000000 R
C11 C 0.59198(18) 0.8066(5) 0.4522(2) 0.0433(7) Uani 1.000000 .
H11 H 0.59040(18) 0.7084(5) 0.4067(2) 0.0519(9) Uiso 1.000000 R
C3 C 0.7583(2) 0.2824(5) 0.4837(2) 0.0465(8) Uani 1.000000 .
H3 H 0.7594(2) 0.1736(5) 0.4434(2) 0.0558(10) Uiso 1.000000 R
C15 C 0.4209(2) 1.3028(5) 0.4277(3) 0.0573(10) Uani 1.000000 .
H15 H 0.3849(2) 1.4129(5) 0.4223(3) 0.0688(12) Uiso 1.000000 R
C13 C 0.5387(2) 1.1440(5) 0.4975(3) 0.0496(8) Uani 1.000000 .
H13 H 0.5812(2) 1.1496(5) 0.5410(3) 0.0595(10) Uiso 1.000000 R
C21 C 0.46563(18) 0.9656(5) 0.3777(2) 0.0423(8) Uani 1.000000 .
C14 C 0.4832(2) 1.3087(5) 0.4902(3) 0.0572(10) Uani 1.000000 .
H14 H 0.4894(2) 1.4207(5) 0.5280(3) 0.0686(12) Uiso 1.000000 R
C7 C 0.9083(2) 0.3101(6) 0.7194(3) 0.0599(10) Uani 1.000000 .
H7 H 0.9418(2) 0.3188(6) 0.7712(3) 0.0719(12) Uiso 1.000000 R
C16 C 0.4092(2) 1.1337(5) 0.3703(2) 0.0508(9) Uani 1.000000 .
C20 C 0.4500(2) 0.7959(6) 0.3208(2) 0.0512(9) Uani 1.000000 .
H20 H 0.4855(2) 0.6845(6) 0.3240(2) 0.0615(10) Uiso 1.000000 R
C5 C 0.8625(2) 0.1189(5) 0.5888(3) 0.0536(9) Uani 1.000000 .
H5 H 0.8648(2) 0.0016(5) 0.5539(3) 0.0643(11) Uiso 1.000000 R
C6 C 0.9103(2) 0.1358(6) 0.6651(3) 0.0635(10) Uani 1.000000 .
H6 H 0.9452(2) 0.0292(6) 0.6816(3) 0.0762(12) Uiso 1.000000 R
C19 C 0.3842(2) 0.7927(7) 0.2615(3) 0.0637(10) Uani 1.000000 .
H19 H 0.3757(2) 0.6799(7) 0.2247(3) 0.0765(13) Uiso 1.000000 R
C17 C 0.3423(2) 1.1230(7) 0.3076(3) 0.0676(12) Uani 1.000000 .
H17 H 0.3063(2) 1.2329(7) 0.3019(3) 0.0811(14) Uiso 1.000000 R
C18 C 0.3293(3) 0.9573(7) 0.2555(3) 0.0734(12) Uani 1.000000 .
H18 H 0.2839(3) 0.9525(7) 0.2158(3) 0.0881(14) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 H1 109.5 . . ?
C1 N1 C9 118.3(3) . . ?
C13 C12 C11 121.3(3) . . ?
C21 C12 C11 120.5(3) . . ?
C21 C12 C13 118.2(3) . . ?
C4 C9 N1 124.3(3) . . ?
C8 C9 N1 116.6(3) . . ?
C8 C9 C4 119.1(3) . . ?
C3 C4 C9 115.8(3) . . ?
C5 C4 C9 118.8(3) . . ?
C5 C4 C3 125.4(3) . . ?
C9 C8 O1 117.8(3) . . ?
C7 C8 O1 121.5(3) . . ?
C7 C8 C9 120.8(3) . . ?
C1 C2 H2 119.73(17) . . ?
C3 C2 H2 119.7(2) . . ?
C3 C2 C1 120.5(3) . . ?
C2 C1 N1 120.8(3) . . ?
C10 C1 N1 115.7(3) . . ?
C10 C1 C2 123.4(3) . . ?
H10 C10 C1 116.54(19) . . ?
C11 C10 C1 126.9(3) . . ?
C11 C10 H10 116.5(2) . . ?
C10 C11 C12 126.9(3) . . ?
H11 C11 C12 116.55(18) . . ?
H11 C11 C10 116.5(2) . . ?
C2 C3 C4 120.1(3) . . ?
H3 C3 C4 119.94(19) . . ?
H3 C3 C2 119.9(2) . . ?
C14 C15 H15 119.2(2) . . ?
C16 C15 H15 119.2(2) . . ?
C16 C15 C14 121.6(3) . . ?
H13 C13 C12 118.64(19) . . ?
C14 C13 C12 122.7(3) . . ?
C14 C13 H13 118.6(2) . . ?
C16 C21 C12 118.9(3) . . ?
C20 C21 C12 123.8(3) . . ?
C20 C21 C16 117.3(3) . . ?
C13 C14 C15 119.5(3) . . ?
H14 C14 C15 120.3(2) . . ?
H14 C14 C13 120.3(2) . . ?
H7 C7 C8 120.1(2) . . ?
C6 C7 C8 119.7(3) . . ?
C6 C7 H7 120.1(2) . . ?
C21 C16 C15 119.1(3) . . ?
C17 C16 C15 121.9(3) . . ?
C17 C16 C21 119.0(4) . . ?
H20 C20 C21 119.28(18) . . ?
C19 C20 C21 121.4(3) . . ?
C19 C20 H20 119.3(3) . . ?
H5 C5 C4 120.0(2) . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 120.0(2) . . ?
C5 C6 C7 121.5(3) . . ?
H6 C6 C7 119.2(2) . . ?
H6 C6 C5 119.2(2) . . ?
H19 C19 C20 119.7(3) . . ?
C18 C19 C20 120.7(4) . . ?
C18 C19 H19 119.7(3) . . ?
H17 C17 C16 119.1(2) . . ?
C18 C17 C16 121.7(4) . . ?
C18 C17 H17 119.1(2) . . ?
C17 C18 C19 119.9(4) . . ?
H18 C18 C19 120.1(3) . . ?
H18 C18 C17 120.1(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C8 1.367(4) . ?
N1 C9 1.361(4) . ?
N1 C1 1.332(4) . ?
C12 C11 1.465(4) . ?
C12 C13 1.376(5) . ?
C12 C21 1.438(4) . ?
C9 C4 1.408(4) . ?
C9 C8 1.420(4) . ?
C4 C3 1.409(5) . ?
C4 C5 1.415(4) . ?
C8 C7 1.355(4) . ?
C2 H2 0.9300 . ?
C2 C1 1.420(4) . ?
C2 C3 1.359(4) . ?
C1 C10 1.459(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.316(4) . ?
C11 H11 0.9300 . ?
C3 H3 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.352(5) . ?
C15 C16 1.410(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.406(4) . ?
C21 C16 1.434(4) . ?
C21 C20 1.419(5) . ?
C14 H14 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.399(5) . ?
C16 C17 1.410(5) . ?
C20 H20 0.9300 . ?
C20 C19 1.363(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.357(5) . ?
C6 H6 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.399(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.351(6) . ?
C18 H18 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C8 C9 N1 -2.8(4) . . . . ?
O1 C8 C9 C4 178.0(3) . . . . ?
O1 C8 C7 C6 -179.1(4) . . . . ?
N1 C9 C4 C3 3.6(4) . . . . ?
N1 C9 C4 C5 -177.1(3) . . . . ?
N1 C9 C8 C7 177.5(3) . . . . ?
N1 C1 C2 C3 3.1(4) . . . . ?
N1 C1 C10 C11 -178.7(3) . . . . ?
C12 C11 C10 C1 178.5(3) . . . . ?
C12 C13 C14 C15 0.3(4) . . . . ?
C12 C21 C16 C15 -0.3(3) . . . . ?
C12 C21 C16 C17 -178.7(3) . . . . ?
C12 C21 C20 C19 178.3(3) . . . . ?
C9 C4 C3 C2 -2.1(3) . . . . ?
C9 C4 C5 C6 -1.2(4) . . . . ?
C9 C8 C7 C6 0.6(4) . . . . ?
C4 C3 C2 C1 -1.0(4) . . . . ?
C4 C5 C6 C7 0.0(4) . . . . ?
C8 C7 C6 C5 0.3(4) . . . . ?
C2 C1 C10 C11 -0.9(4) . . . . ?
C15 C16 C21 C20 178.1(3) . . . . ?
C15 C16 C17 C18 -177.2(4) . . . . ?
C21 C16 C17 C18 1.2(4) . . . . ?
C21 C20 C19 C18 -0.5(4) . . . . ?
C16 C17 C18 C19 -1.6(5) . . . . ?
C20 C19 C18 C17 1.3(5) . . . . ?
