# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_hq
_database_code_depnum_ccdc_archive 'CCDC 1584152'
_audit_update_record             
;
2017-11-06 deposited with the CCDC.
2017-12-22 downloaded from the CCDC.
;

_publ_contact_name               'Fedyanin, Ivan V.'
_publ_contact_email              octy@xrlab.ineos.ac.ru

_audit_creation_method           'Modified SHELXL output'
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        8-hydroxyquinoline
_chemical_name_common            quinoline-8-ol
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H7 N O'
_chemical_formula_sum            'C9 H7 N O'
_chemical_formula_weight         145.16

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   24.9340(4)
_cell_length_b                   28.5658(4)
_cell_length_c                   3.77780(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2690.77(9)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6533
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      60.65

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'ο scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            75800
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_limit_h_min       -60
_diffrn_reflns_limit_h_max       60
_diffrn_reflns_limit_k_min       -67
_diffrn_reflns_limit_k_max       69
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.168
_diffrn_reflns_theta_max         59.997
_diffrn_reflns_theta_full        59.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             9760
_reflns_number_gt                8743
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_max     0.912
_reflns_Friedel_fraction_full    0.912

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          'IAM refinement'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0546P)²+0.2500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3546 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         9760
_refine_ls_number_parameters     104
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0831
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.06661(2) -0.03254(2) 0.15004(12) 0.01554(5) Uani 1 1 d . . . . .
H1 H 0.0335(6) -0.0261(5) 0.248(5) 0.031(3) Uiso 1 1 d . . . . .
N1 N 0.03313(2) 0.05031(2) 0.45785(10) 0.01142(4) Uani 1 1 d . . . . .
C2 C 0.01829(2) 0.08964(2) 0.61462(12) 0.01249(5) Uani 1 1 d . . . . .
H2 H -0.0185 0.0934 0.6739 0.015 Uiso 1 1 calc R U . . .
C3 C 0.05408(2) 0.12628(2) 0.69874(13) 0.01333(5) Uani 1 1 d . . . . .
H3 H 0.0415 0.1540 0.8104 0.016 Uiso 1 1 calc R U . . .
C4 C 0.10746(2) 0.12127(2) 0.61654(12) 0.01278(5) Uani 1 1 d . . . . .
H4 H 0.1322 0.1456 0.6693 0.015 Uiso 1 1 calc R U . . .
C4A C 0.12524(2) 0.07953(2) 0.45254(10) 0.01064(4) Uani 1 1 d . . . . .
C5 C 0.17952(2) 0.07188(2) 0.35696(12) 0.01289(5) Uani 1 1 d . . . . .
H5 H 0.2059 0.0951 0.4052 0.015 Uiso 1 1 calc R U . . .
C6 C 0.19377(2) 0.03069(2) 0.19387(12) 0.01353(5) Uani 1 1 d . . . . .
H6 H 0.2301 0.0258 0.1269 0.016 Uiso 1 1 calc R U . . .
C7 C 0.15542(2) -0.00453(2) 0.12408(12) 0.01312(5) Uani 1 1 d . . . . .
H7 H 0.1662 -0.0328 0.0124 0.016 Uiso 1 1 calc R U . . .
C8 C 0.10236(2) 0.00178(2) 0.21683(11) 0.01135(4) Uani 1 1 d . . . . .
C8A C 0.08615(2) 0.04463(2) 0.37969(10) 0.01001(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C8 1.3488(5) . ?
O1 H1 0.922(15) . ?
N1 C2 1.3228(5) . ?
N1 C8A 1.3643(4) . ?
C2 C3 1.4118(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.3743(5) . ?
C3 H3 0.9500 . ?
C4 C4A 1.4150(5) . ?
C4 H4 0.9500 . ?
C4A C5 1.4177(5) . ?
C4A C8A 1.4212(5) . ?
C5 C6 1.3749(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.4130(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.3803(5) . ?
C7 H7 0.9500 . ?
C8 C8A 1.4282(5) . ?

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 111.8(9) . . ?
C2 N1 C8A 117.98(3) . . ?
N1 C2 C3 123.61(3) . . ?
N1 C2 H2 118.2 . . ?
C3 C2 H2 118.2 . . ?
C4 C3 C2 118.96(3) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C4A 119.35(3) . . ?
C3 C4 H4 120.3 . . ?
C4A C4 H4 120.3 . . ?
C4 C4A C5 122.71(3) . . ?
C4 C4A C8A 117.46(3) . . ?
C5 C4A C8A 119.82(3) . . ?
C6 C5 C4A 119.52(3) . . ?
C6 C5 H5 120.2 . . ?
C4A C5 H5 120.2 . . ?
C5 C6 C7 121.20(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 120.55(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
O1 C8 C7 119.41(3) . . ?
O1 C8 C8A 121.09(3) . . ?
C7 C8 C8A 119.51(3) . . ?
N1 C8A C4A 122.63(3) . . ?
N1 C8A C8 118.00(3) . . ?
C4A C8A C8 119.37(3) . . ?

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
C8A N1 C2 C3 1.29(6) . . . . ?
N1 C2 C3 C4 -0.33(7) . . . . ?
C2 C3 C4 C4A -0.44(7) . . . . ?
C3 C4 C4A C5 179.46(4) . . . . ?
C3 C4 C4A C8A 0.23(6) . . . . ?
C4 C4A C5 C6 -179.11(4) . . . . ?
C8A C4A C5 C6 0.10(6) . . . . ?
C4A C5 C6 C7 -0.92(7) . . . . ?
C5 C6 C7 C8 0.38(7) . . . . ?
C6 C7 C8 O1 -179.44(4) . . . . ?
C6 C7 C8 C8A 0.97(6) . . . . ?
C2 N1 C8A C4A -1.50(6) . . . . ?
C2 N1 C8A C8 178.78(4) . . . . ?
C4 C4A C8A N1 0.75(6) . . . . ?
C5 C4A C8A N1 -178.49(4) . . . . ?
C4 C4A C8A C8 -179.52(4) . . . . ?
C5 C4A C8A C8 1.23(6) . . . . ?
O1 C8 C8A N1 -1.60(6) . . . . ?
C7 C8 C8A N1 177.98(4) . . . . ?
O1 C8 C8A C4A 178.66(4) . . . . ?
C7 C8 C8A C4A -1.76(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.922(15) 1.968(15) 2.7920(5) 147.9(12) 2

_refine_diff_density_max         0.591
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.072


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_hq-mm
_database_code_depnum_ccdc_archive 'CCDC 1584153'
_audit_update_record             
;
2017-11-06 deposited with the CCDC.
2017-12-22 downloaded from the CCDC.
;

_audit_creation_date             '06-Jun-06 T15:16:19-00:00'
_audit_creation_method           'Modified XDCIF output'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------# 
#                   CHEMICAL INFORMATION                                     # 
#----------------------------------------------------------------------------# 

_chemical_formula_moiety         'C9 H7 N O'
_chemical_formula_sum            'C9 H7 N O'
_chemical_formula_weight         145.16

#----------------------------------------------------------------------------# 
#                   UNIT CELL INFORMATION                                    # 
#----------------------------------------------------------------------------# 

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +x,+y,+z
2 -x,-y,+z
3 1/4+x,1/4-y,1/4+z
4 1/4-x,1/4+y,1/4+z
5 1/2+x,1/2+y,+z
6 1/2-x,1/2-y,+z
7 3/4+x,3/4-y,1/4+z
8 3/4-x,3/4+y,1/4+z
9 1/2+x,+y,1/2+z
10 1/2-x,-y,1/2+z
11 3/4+x,1/4-y,3/4+z
12 3/4-x,1/4+y,3/4+z
13 +x,1/2+y,1/2+z
14 -x,1/2-y,1/2+z
15 1/4+x,3/4-y,3/4+z
16 1/4-x,3/4+y,3/4+z

_cell_length_a                   24.9340(4)
_cell_length_b                   28.5658(4)
_cell_length_c                   3.77780(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2690.77(9)
_cell_formula_units_Z            16
_cell_measurement_temperature    100
_cell_measurement_reflns_used    6533
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      60.65

#----------------------------------------------------------------------------# 
#                   CRYSTAL INFORMATION                                      # 
#----------------------------------------------------------------------------# 

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_F_000             1216

#----------------------------------------------------------------------------# 
#                   ABSORPTION CORRECTION                                    # 
#----------------------------------------------------------------------------# 

_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_T_max  0.864

#----------------------------------------------------------------------------# 
#                   DATA COLLECTION                                          # 
#----------------------------------------------------------------------------# 

_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_ambient_temperature      100
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector                 'Bruker APEX II CCD area detector'
_diffrn_measurement_device       'Bruker APEX II'
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_number            75800
_diffrn_reflns_limit_h_min       -60
_diffrn_reflns_limit_h_max       60
_diffrn_reflns_limit_k_min       -67
_diffrn_reflns_limit_k_max       69
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.168
_diffrn_reflns_theta_max         59.997
_diffrn_reflns_theta_full        59.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             5843
_reflns_number_gt                4966
_reflns_threshold_expression     F>3σ(F)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_structure_refinement  'Volkov et al, (2006)'
_computing_molecular_graphics    'Volkov et al, (2006)'
_computing_publication_material  'Volkov et al, (2006)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          'Multipole refinement'
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
        calc w1 = [Fo*sqrt(w2) + sqrt(Fo²w2² + sqrt(w2²))]²
        where
     calc w2 = q/[s²(Fo²) + (0.01 P)² + 0.01 P + 0.00 + 0.00 sin(th)]
     where P = (0.3333 Fo² + 0.6667 Fc²)
           q = 1.0
;
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4966
_refine_ls_number_parameters     1
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.02
_refine_ls_R_factor_gt           0.014
_refine_ls_wR_factor_ref         0.012
_refine_ls_goodness_of_fit_ref   1.285
_refine_ls_shift/su_max          0

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.096
_refine_diff_density_rms         0.022

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_occupancy
_atom_site_symmetry_multiplicity
O(1) O 0.066547(5) -0.032501(4) 0.1504(8) 0.016 1 16
N(1) N 0.033157(5) 0.050333(4) 0.4586(8) 0.011 1 16
C(2) C 0.018267(6) 0.089633(5) 0.6151(8) 0.012 1 16
C(3) C 0.054070(6) 0.126280(5) 0.6993(8) 0.013 1 16
C(4) C 0.107466(6) 0.121281(5) 0.6174(8) 0.013 1 16
C(4A) C 0.125249(5) 0.079505(5) 0.4533(8) 0.011 1 16
C(5) C 0.179524(6) 0.071893(5) 0.3578(8) 0.013 1 16
C(6) C 0.193810(6) 0.030678(5) 0.1945(8) 0.013 1 16
C(7) C 0.155440(6) -0.004545(5) 0.1248(8) 0.013 1 16
C(8) C 0.102347(6) 0.001770(5) 0.2176(8) 0.011 1 16
C(8A) C 0.086144(5) 0.044625(4) 0.3806(8) 0.01 1 16
H(1) H 0.031049 -0.025606 0.254867 0.027 1 16
H(2) H -0.023629 0.093964 0.682172 0.029 1 16
H(3) H 0.039698 0.157848 0.826016 0.031 1 16
H(4) H 0.135649 0.148996 0.6767 0.031 1 16
H(5) H 0.209543 0.09829 0.411992 0.031 1 16
H(6) H 0.235125 0.025151 0.117546 0.031 1 16
H(7) H 0.167731 -0.0367 -0.003019 0.03 1 16



#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
O(1) 6.1034(15) 0 -0.084(6) 0.015(9) -0.025(4) -0.037(4) 0.029(3) -0.016(4)
0.004(4) -0.044(4) 0.046(6) -0.020(5) -0.002(7) -0.061(9) -0.003(7) -0.013(9)
0.001(5) 0 0 0 0 0 0 0 0 0 1.003123 0.985(15) 0.985(15) 0.985(15) 0.985(15)
0.985(15)
N(1) 5.20(2) 0 0.007(6) -0.012(10) -0.111(5) 0.126(4) 0.013(4) -0.012(4)
0.114(4) -0.012(4) -0.088(6) -0.005(6) -0.008(7) 0.087(8) 0.010(8) -0.026(9)
-0.004(6) 0 0 0 0 0 0 0 0 0 1.001262 0.984(9) 0.984(9) 0.984(9) 0.984(9)
0.984(9)
C(2) 3.98(2) 0 0.041(8) 0.020(14) -0.009(7) 0.115(6) -0.005(5) 0.012(6)
0.176(6) -0.017(6) 0.240(9) -0.016(8) 0.013(10) -0.221(11) 0.017(11) 0.021(11)
0.013(9) 0 0 0 0 0 0 0 0 0 1.019097 0.974(7) 0.974(7) 0.974(7) 0.974(7)
0.974(7)
C(3) 4.06(2) 0 0.029(8) 0.023(13) 0.041(7) 0.124(6) 0.004(5) -0.002(6) 0.155(6)
-0.027(6) 0.211(10) -0.011(8) 0.002(12) -0.193(9) 0.006(9) 0.017(11) 0.001(8) 0
0 0 0 0 0 0 0 0 1.018636 0.989(8) 0.989(8) 0.989(8) 0.989(8) 0.989(8)
C(4) 4.02(2) 0 0.023(7) 0.030(13) -0.002(8) 0.099(6) -0.014(5) -0.017(6)
0.179(5) -0.007(6) 0.223(10) -0.000(8) 0.000(7) -0.123(11) 0.011(9) -0.021(8)
0.013(12) 0 0 0 0 0 0 0 0 0 1.015322 0.998(9) 0.998(9) 0.998(9) 0.998(9)
0.998(9)
C(4A) 4.09(2) 0 -0.005(8) 0.014(13) -0.025(7) 0.090(6) 0.004(5) -0.015(6)
0.187(6) 0.015(6) 0.233(9) -0.020(8) 0.014(9) -0.162(10) 0.007(11) -0.016(11)
0.009(8) 0 0 0 0 0 0 0 0 0 1.016075 0.981(8) 0.981(8) 0.981(8) 0.981(8)
0.981(8)
C(5) 4.05(2) 0 0.011(7) 0.024(14) 0.047(9) 0.125(6) 0.007(6) -0.025(6) 0.131(5)
0.010(6) 0.246(11) -0.018(8) 0.005(8) -0.155(11) 0.001(8) -0.020(8) 0.013(12) 0
0 0 0 0 0 0 0 0 1.017058 0.978(9) 0.978(9) 0.978(9) 0.978(9) 0.978(9)
C(6) 3.98(2) 0 0.025(9) 0.023(13) 0.040(7) 0.106(6) -0.046(6) 0.006(6) 0.176(6)
0.007(6) 0.238(8) 0.006(8) 0.035(10) -0.135(10) -0.002(10) -0.066(12) 0.014(8)
0 0 0 0 0 0 0 0 0 1.014679 0.980(8) 0.980(8) 0.980(8) 0.980(8) 0.980(8)
C(7) 4.03(2) 0 0.000(9) 0.026(13) 0.024(8) 0.077(5) -0.016(6) 0.000(6) 0.133(6)
0.005(6) 0.196(10) -0.005(8) 0.016(11) -0.165(9) 0.008(9) -0.056(11) 0.010(7) 0
0 0 0 0 0 0 0 0 1.018042 0.992(10) 0.992(10) 0.992(10) 0.992(10) 0.992(10)
C(8) 4.11(2) 0 0.033(8) -0.015(12) -0.049(7) 0.078(6) -0.029(5) 0.022(6)
0.209(6) 0.017(6) 0.324(8) -0.012(9) -0.016(10) -0.146(9) -0.002(10) 0.015(12)
-0.005(8) 0 0 0 0 0 0 0 0 0 1.010683 0.978(7) 0.978(7) 0.978(7) 0.978(7)
0.978(7)
C(8A) 4.14(2) 0 0.030(8) 0.003(14) -0.011(7) 0.089(5) -0.003(5) 0.005(6)
0.158(6) 0.026(6) 0.268(10) 0.045(8) 0.006(12) -0.183(9) -0.001(9) -0.049(13)
0.017(8) 0 0 0 0 0 0 0 0 0 1.01127 0.971(7) 0.971(7) 0.971(7) 0.971(7) 0.971(7)
H(1) 0.775(8) 0 0 0 0.270(7) 0.223(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
1.2 1.2 1.2 1.2 1.2 1.2
H(2) 0.909(8) 0 0 0 0.145(6) 0.107(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
1.2 1.2 1.2 1.2 1.2 1.2
H(3) 0.889(8) 0 0 0 0.151(7) 0.081(10) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
1.2 1.2 1.2 1.2 1.2 1.2
H(4) 0.907(8) 0 0 0 0.153(7) 0.101(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
1.2 1.2 1.2 1.2 1.2 1.2
H(5) 0.939(8) 0 0 0 0.144(7) 0.106(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
1.2 1.2 1.2 1.2 1.2 1.2
H(6) 0.927(8) 0 0 0 0.144(7) 0.107(10) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
1.2 1.2 1.2 1.2 1.2 1.2
H(7) 0.902(8) 0 0 0 0.155(7) 0.065(10) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
1.2 1.2 1.2 1.2 1.2 1.2

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
O(1) C(8) Z O(1) H(1) X
N(1) C(4) Z N(1) C(2) X
C(2) C(3) Z C(2) N(1) X
C(3) C(4) Z C(3) C(2) X
C(4) C(4A) Z C(4) C(3) X
C(4A) C(8A) Z C(4A) C(4) X
C(5) C(6) Z C(5) C(4A) X
C(6) C(7) Z C(6) C(5) X
C(7) C(8) Z C(7) C(6) X
C(8) O(1) Z C(8) C(7) X
C(8A) N(1) Z C(8A) C(4A) X
H(1) O(1) Z H(1) C(8) X
H(2) C(2) Z H(2) N(1) X
H(3) C(3) Z H(3) C(4) X
H(4) C(4) Z H(4) C(3) X
H(5) C(5) Z H(5) C(6) X
H(6) C(6) Z H(6) C(5) X
H(7) C(7) Z H(7) C(8) X


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(1) C(8) 1.34897(18) 1_555 1_555 yes
O(1) H(1) 0.9890(12) 1_555 1_555 yes
N(1) C(2) 1.3220(2) 1_555 1_555 yes
N(1) C(8A) 1.36346(18) 1_555 1_555 yes
C(2) C(3) 1.4121(2) 1_555 1_555 yes
C(2) H(2) 1.0820(7) 1_555 1_555 yes
C(3) C(4) 1.3743(2) 1_555 1_555 yes
C(3) H(3) 1.0820(13) 1_555 1_555 yes
C(4) C(4A) 1.4161(2) 1_555 1_555 yes
C(4) H(4) 1.0820(6) 1_555 1_555 yes
C(4A) C(5) 1.4173(2) 1_555 1_555 yes
C(4A) C(8A) 1.42084(18) 1_555 1_555 yes
C(5) C(6) 1.3761(2) 1_555 1_555 yes
C(5) H(5) 1.0820(6) 1_555 1_555 yes
C(6) C(7) 1.4132(2) 1_555 1_555 yes
C(6) H(6) 1.0820(8) 1_555 1_555 yes
C(7) C(8) 1.3813(2) 1_555 1_555 yes
C(7) H(7) 1.0820(13) 1_555 1_555 yes
C(8) C(8A) 1.42868(19) 1_555 1_555 yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(8) O(1) H(1) 111.87(6) 1_555 1_555 1_555 yes
C(2) N(1) C(8A) 118.059(12) 1_555 1_555 1_555 yes
N(1) C(2) C(3) 123.554(14) 1_555 1_555 1_555 yes
N(1) C(2) H(2) 118.22(6) 1_555 1_555 1_555 yes
C(3) C(2) H(2) 118.22(6) 1_555 1_555 1_555 yes
C(2) C(3) C(4) 118.995(13) 1_555 1_555 1_555 yes
C(2) C(3) H(3) 120.538(14) 1_555 1_555 1_555 yes
C(4) C(3) H(3) 120.467(14) 1_555 1_555 1_555 yes
C(3) C(4) C(4A) 119.307(13) 1_555 1_555 1_555 yes
C(3) C(4) H(4) 120.43(6) 1_555 1_555 1_555 yes
C(4A) C(4) H(4) 120.26(6) 1_555 1_555 1_555 yes
C(4) C(4A) C(5) 122.661(13) 1_555 1_555 1_555 yes
C(4) C(4A) C(8A) 117.431(12) 1_555 1_555 1_555 yes
C(5) C(4A) C(8A) 119.904(13) 1_555 1_555 1_555 yes
C(4A) C(5) C(6) 119.503(13) 1_555 1_555 1_555 yes
C(4A) C(5) H(5) 120.37(6) 1_555 1_555 1_555 yes
C(6) C(5) H(5) 120.13(7) 1_555 1_555 1_555 yes
C(5) C(6) C(7) 121.164(14) 1_555 1_555 1_555 yes
C(5) C(6) H(6) 119.46(6) 1_555 1_555 1_555 yes
C(7) C(6) H(6) 119.38(6) 1_555 1_555 1_555 yes
C(6) C(7) C(8) 120.566(13) 1_555 1_555 1_555 yes
C(6) C(7) H(7) 119.727(15) 1_555 1_555 1_555 yes
C(8) C(7) H(7) 119.708(15) 1_555 1_555 1_555 yes
O(1) C(8) C(7) 119.447(13) 1_555 1_555 1_555 yes
O(1) C(8) C(8A) 121.057(12) 1_555 1_555 1_555 yes
C(7) C(8) C(8A) 119.494(13) 1_555 1_555 1_555 yes
N(1) C(8A) C(4A) 122.638(12) 1_555 1_555 1_555 yes
N(1) C(8A) C(8) 118.014(12) 1_555 1_555 1_555 yes
C(4A) C(8A) C(8) 119.346(12) 1_555 1_555 1_555 yes
_chemical_name_systematic        8-hydroxyquinoline
_chemical_name_common            quinoline-8-ol
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
