#------------------------------------------------------------------------------
#$Date: 2019-11-17 11:47:45 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229689 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/79/7047997.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_7047997
loop_
_publ_author_name
'Pape, Veronika F. S.'
'May, Nóra V'
'Gál, G Tamás'
'Szatmári, István'
'Szeri, Flóra'
'Fülöp, Ferenc'
'Szakács, Gergely'
'Enyedy, Éva A'
_publ_section_title
;
 Impact of copper and iron binding properties on the anticancer activity
 of 8-hydroxyquinoline derived Mannich bases.
;
_journal_issue                   47
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              17032
_journal_page_last               17045
_journal_paper_doi               10.1039/c8dt03088j
_journal_volume                  47
_journal_year                    2018
_chemical_formula_moiety         'C15 H18 N2 O'
_chemical_formula_sum            'C15 H18 N2 O'
_chemical_formula_weight         242.31
_chemical_name_systematic        7-(piperidin-1-ylmethyl)quinolin-8-ol
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-09-18 deposited with the CCDC.
2018-11-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9362(7)
_cell_length_b                   11.4735(10)
_cell_length_c                   12.7458(11)
_cell_measurement_reflns_used    24530
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      3.20
_cell_volume                     1306.82(19)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_molecular_graphics    'Mercury (Macrae, 2006)'
_computing_publication_material  'Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Sir2014 (Burla, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
 scan:  N=1,PHI=0.0,CHI=40.0,OMEGA=20.0,200.0,5.0,COUPLE=0.00                  
 scan:  N=2,PHI=180.0,CHI=40.0,OMEGA=20.0,200.0,5.0,COUPLE=0.00                
 scan:  N=3,PHI=0.0,CHI=0.0,OMEGA=20.0,200.0,5.0,COUPLE=0.00                   
 scan:  N=4,PHI=90.0,CHI=0.0,OMEGA=20.0,200.0,5.0,COUPLE=0.00                  
 Orientation Matrix:
    UB11 -0.0633 UB12 -0.0285 UB13 -0.0594
    UB21  0.0213 UB22  0.0734 UB23 -0.0396
    UB31  0.0898 UB32 -0.0375 UB33 -0.0325
    Matrix type: 'd*Trek'
;
_diffrn_measurement_device       RAXIS-RAPID
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_detector       RX
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            41004
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.397
_diffrn_reflns_theta_min         3.197
_diffrn_source_current           40.0000
_diffrn_source_power             2.0000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9629
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
 T.Higashi, Numerical Absorption Correction, NUMABS, 2002
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       Chunk
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 775 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2956
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0895P)²+0.0073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1493
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2309
_reflns_number_total             2956
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8dt03088j2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Numerical' changed to
'numerical' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7047997--7048001.cif.
;
_cod_database_code               7047997
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.977
_shelx_estimated_absorpt_t_max   0.981
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.8570(2) 0.81438(17) 0.32001(14) 0.0633(5) Uani 1 1 d . .
C7 C 0.7215(3) 0.7990(2) 0.48149(18) 0.0561(6) Uani 1 1 d . .
N10 N 0.6900(2) 0.62856(18) 0.36243(17) 0.0599(6) Uani 1 1 d . .
N1 N 0.9062(3) 1.0459(2) 0.35370(17) 0.0652(6) Uani 1 1 d . .
C8A C 0.8222(2) 0.9858(2) 0.42484(18) 0.0530(6) Uani 1 1 d . .
C8 C 0.7989(3) 0.8638(2) 0.40897(17) 0.0528(6) Uani 1 1 d . .
C4A C 0.7583(3) 1.0393(2) 0.51473(19) 0.0585(6) Uani 1 1 d . .
C6 C 0.6585(3) 0.8549(3) 0.56959(19) 0.0658(7) Uani 1 1 d . .
H6 H 0.6043 0.8106 0.6175 0.079 Uiso 1 1 calc R U
C9 C 0.7147(3) 0.6671(2) 0.4713(2) 0.0697(8) Uani 1 1 d . .
H9A H 0.8078 0.6340 0.4968 0.084 Uiso 1 1 calc R U
H9B H 0.6344 0.6377 0.5151 0.092(10) Uiso 1 1 calc R .
C5 C 0.6741(3) 0.9720(3) 0.5870(2) 0.0670(7) Uani 1 1 d . .
H5 H 0.6303 1.0068 0.6453 0.080 Uiso 1 1 calc R U
C2 C 0.9277(4) 1.1583(3) 0.3726(2) 0.0775(8) Uani 1 1 d . .
H2 H 0.9838 1.2004 0.3243 0.093 Uiso 1 1 calc R U
C11 C 0.5366(3) 0.6540(2) 0.3300(2) 0.0601(6) Uani 1 1 d . .
H11A H 0.5179 0.7369 0.3373 0.072 Uiso 1 1 calc R U
H11B H 0.4675 0.6131 0.3758 0.072 Uiso 1 1 calc R U
C13 C 0.5403(4) 0.4890(3) 0.2030(3) 0.0837(9) Uani 1 1 d . .
H13B H 0.4684 0.4433 0.2424 0.100 Uiso 1 1 calc R U
H13A H 0.5309 0.4688 0.1295 0.100 Uiso 1 1 calc R U
C4 C 0.7866(3) 1.1591(2) 0.5301(2) 0.0728(8) Uani 1 1 d . .
H4 H 0.7468 1.1975 0.5880 0.087 Uiso 1 1 calc R U
C15 C 0.7200(4) 0.5026(3) 0.3515(3) 0.0877(10) Uani 1 1 d . .
H15A H 0.6542 0.4595 0.3980 0.105 Uiso 1 1 calc R U
H15B H 0.8224 0.4866 0.3722 0.105 Uiso 1 1 calc R U
C12 C 0.5083(4) 0.6179(3) 0.2179(2) 0.0761(9) Uani 1 1 d . .
H12B H 0.5718 0.6631 0.1714 0.091 Uiso 1 1 calc R U
H12A H 0.4049 0.6339 0.1997 0.091 Uiso 1 1 calc R U
C3 C 0.8722(4) 1.2181(3) 0.4599(3) 0.0807(9) Uani 1 1 d . .
H3 H 0.8934 1.2967 0.4697 0.097 Uiso 1 1 calc R U
C14 C 0.6960(4) 0.4619(3) 0.2404(4) 0.1014(12) Uani 1 1 d . .
H14A H 0.7681 0.4997 0.1948 0.122 Uiso 1 1 calc R U
H14B H 0.7128 0.3785 0.2366 0.122 Uiso 1 1 calc R U
H1O H 0.804(6) 0.737(4) 0.326(4) 0.124(14) Uiso 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 O1 H1O 97(3)
C8 C7 C6 119.4(2)
C8 C7 C9 120.1(2)
C6 C7 C9 120.3(2)
C11 N10 C9 110.3(2)
C11 N10 C15 109.8(2)
C9 N10 C15 110.8(2)
C2 N1 C8A 116.8(2)
N1 C8A C4A 122.7(2)
N1 C8A C8 118.8(2)
C4A C8A C8 118.6(2)
O1 C8 C7 121.6(2)
O1 C8 C8A 117.8(2)
C7 C8 C8A 120.6(2)
C4 C4A C5 122.4(3)
C4 C4A C8A 117.4(2)
C5 C4A C8A 120.2(2)
C5 C6 C7 122.3(2)
C5 C6 H6 118.8
C7 C6 H6 118.8
N10 C9 C7 112.7(2)
N10 C9 H9A 109.1
C7 C9 H9A 109.1
N10 C9 H9B 109.1
C7 C9 H9B 109.1
H9A C9 H9B 107.8
C6 C5 C4A 118.9(2)
C6 C5 H5 120.6
C4A C5 H5 120.6
N1 C2 C3 124.8(3)
N1 C2 H2 117.6
C3 C2 H2 117.6
N10 C11 C12 111.7(2)
N10 C11 H11A 109.3
C12 C11 H11A 109.3
N10 C11 H11B 109.3
C12 C11 H11B 109.3
H11A C11 H11B 107.9
C14 C13 C12 109.7(3)
C14 C13 H13B 109.7
C12 C13 H13B 109.7
C14 C13 H13A 109.7
C12 C13 H13A 109.7
H13B C13 H13A 108.2
C3 C4 C4A 119.7(3)
C3 C4 H4 120.1
C4A C4 H4 120.1
N10 C15 C14 111.5(3)
N10 C15 H15A 109.3
C14 C15 H15A 109.3
N10 C15 H15B 109.3
C14 C15 H15B 109.3
H15A C15 H15B 108.0
C11 C12 C13 110.7(3)
C11 C12 H12B 109.5
C13 C12 H12B 109.5
C11 C12 H12A 109.5
C13 C12 H12A 109.5
H12B C12 H12A 108.1
C4 C3 C2 118.6(3)
C4 C3 H3 120.7
C2 C3 H3 120.7
C13 C14 C15 111.4(3)
C13 C14 H14A 109.3
C15 C14 H14A 109.3
C13 C14 H14B 109.3
C15 C14 H14B 109.3
H14A C14 H14B 108.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.370(3)
O1 H1O 1.01(5)
C7 C8 1.373(3)
C7 C6 1.411(4)
C7 C9 1.520(4)
N10 C11 1.461(3)
N10 C9 1.473(3)
N10 C15 1.477(4)
N1 C2 1.326(4)
N1 C8A 1.364(3)
C8A C4A 1.420(3)
C8A C8 1.430(3)
C4A C4 1.412(4)
C4A C5 1.418(4)
C6 C5 1.369(4)
C6 H6 0.9300
C9 H9A 0.9700
C9 H9B 0.9700
C5 H5 0.9300
C2 C3 1.398(4)
C2 H2 0.9300
C11 C12 1.510(4)
C11 H11A 0.9700
C11 H11B 0.9700
C13 C14 1.503(5)
C13 C12 1.518(5)
C13 H13B 0.9700
C13 H13A 0.9700
C4 C3 1.357(4)
C4 H4 0.9300
C15 C14 1.506(6)
C15 H15A 0.9700
C15 H15B 0.9700
C12 H12B 0.9700
C12 H12A 0.9700
C3 H3 0.9300
C14 H14A 0.9700
C14 H14B 0.9700
