#------------------------------------------------------------------------------
#$Date: 2022-03-02 05:20:08 +0200 (Wed, 02 Mar 2022) $
#$Revision: 273207 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/64/1566458.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1566458
loop_
_publ_author_name
'Ruth, Paul Niklas'
'Herbst-Irmer, Regine'
'Stalke, Dietmar'
_publ_section_title
;
 Hirshfeld atom refinement based on projector augmented wave densities
 with periodic boundary conditions
;
_journal_issue                   2
_journal_name_full               IUCrJ
_journal_page_first              286
_journal_page_last               297
_journal_paper_doi               10.1107/S2052252522001385
_journal_volume                  9
_journal_year                    2022
_chemical_formula_moiety         'C9 H8 N O, C4 H3 O4'
_chemical_formula_sum            'C13 H11 N O5'
_chemical_formula_weight         261.2363
_chemical_name_common            '8-hydroxyquinolinium hydrogen maleate'
_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'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           'xHARPY 0.1'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.33860(10)
_cell_length_b                   9.9878(2)
_cell_length_c                   22.3493(4)
_cell_measurement_reflns_used    100369
_cell_measurement_temperature    15(2)
_cell_measurement_theta_max      26.19
_cell_measurement_theta_min      0.91
_cell_volume                     1191.68(4)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_publication_material  'xHARPY 0.1'
_computing_structure_refinement  'xHARPY 0.1'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      15(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  IPDSC-Q
_diffrn_measurement_method       'phi or omega oscillation scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.35307
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            80044
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        12.23
_diffrn_reflns_theta_max         24.239
_diffrn_reflns_theta_min         0.905
_diffrn_source                   SPring-8
_exptl_absorpt_coefficient_mu    0.038
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.119
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.4473
_refine_diff_density_min         -0.4692
_refine_diff_density_rms         0.0673
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.5
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         15641
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.0
_refine_ls_shift/su_mean         0.0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/[σ²(Fo²)]
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0398
_refine_ls_wR_factor_ref         0.0407
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_full    1.0
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                12928
_reflns_number_total             15641
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            fc5060.cif
_cod_data_source_block           HMa-8HQ_xHARPy_PBE
_cod_database_code               1566458
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
O5 O 1.67646(4) 0.21643(3) 0.541815(9) 0.01435(4) Uani 1.0 1
H5 H 1.7217(14) 0.1723(7) 0.5056(3) 0.0320(18) Uani 1.0 1
N1 N 1.52242(4) 0.29948(3) 0.649895(10) 0.00978(4) Uani 1.0 1
H4 H 1.4301(12) 0.3331(7) 0.6114(3) 0.0270(16) Uani 1.0 1
C5 C 1.71228(5) 0.20834(3) 0.646389(11) 0.00963(4) Uani 1.0 1
C6 C 1.79202(5) 0.16234(3) 0.589300(11) 0.01119(4) Uani 1.0 1
C7 C 1.98004(6) 0.06754(3) 0.586770(13) 0.01521(5) Uani 1.0 1
H6 H 2.0423(11) 0.0333(5) 0.5428(2) 0.0275(14) Uani 1.0 1
C8 C 2.09169(7) 0.01805(4) 0.639828(14) 0.01681(5) Uani 1.0 1
H7 H 2.2351(12) -0.0581(6) 0.6352(3) 0.0387(17) Uani 1.0 1
C9 C 2.02035(6) 0.06446(3) 0.695314(13) 0.01478(5) Uani 1.0 1
H8 H 2.1115(13) 0.0266(6) 0.7353(3) 0.0355(16) Uani 1.0 1
C10 C 1.82754(5) 0.16178(3) 0.699624(12) 0.01072(4) Uani 1.0 1
C11 C 1.74122(6) 0.21444(3) 0.754727(11) 0.01168(4) Uani 1.0 1
H9 H 1.8256(11) 0.1812(6) 0.7964(2) 0.0336(16) Uani 1.0 1
C12 C 1.55044(6) 0.30735(3) 0.755709(12) 0.01164(4) Uani 1.0 1
H10 H 1.4777(11) 0.3462(5) 0.7979(2) 0.0302(14) Uani 1.0 1
C13 C 1.44213(5) 0.34828(3) 0.701766(12) 0.01083(4) Uani 1.0 1
H11 H 1.2873(10) 0.4173(5) 0.6987(2) 0.0252(14) Uani 1.0 1
O1 O 0.64276(5) 0.62232(2) 0.647771(10) 0.01475(4) Uani 1.0 1
H1 H 0.8017(15) 0.5627(7) 0.6433(3) 0.029(2) Uani 1.0 1
O2 O 1.01586(4) 0.48361(2) 0.634414(9) 0.01274(4) Uani 1.0 1
O3 O 0.41196(5) 0.75682(2) 0.592025(10) 0.01726(4) Uani 1.0 1
O4 O 1.25526(4) 0.41263(2) 0.559773(9) 0.01220(4) Uani 1.0 1
C1 C 0.58575(6) 0.67795(3) 0.596472(12) 0.01149(4) Uani 1.0 1
C2 C 0.73566(6) 0.64414(3) 0.541927(12) 0.01113(4) Uani 1.0 1
H2 H 0.6658(11) 0.6959(6) 0.5025(2) 0.0282(15) Uani 1.0 1
C3 C 0.93453(6) 0.56298(3) 0.534625(11) 0.01083(4) Uani 1.0 1
H3 H 1.0113(11) 0.5576(6) 0.4898(2) 0.0271(14) Uani 1.0 1
C4 C 1.07526(5) 0.48124(3) 0.579638(11) 0.00966(4) Uani 1.0 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C -0.0005 0.0003 'HAR in xHARPy 0.1'
H H 0.0000 0.0000 'HAR in xHARPy 0.1'
N N -0.0002 0.0007 'HAR in xHARPy 0.1'
O O 0.0004 0.0013 'HAR in xHARPy 0.1'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 O5 H5 111.7(4)
C13 N1 C5 122.31(2)
C13 N1 H4 116.6(3)
C5 N1 H4 121.1(3)
N1 C5 C10 119.53(2)
N1 C5 C6 119.32(2)
C10 C5 C6 121.15(2)
O5 C6 C7 125.32(2)
O5 C6 C5 116.25(2)
C7 C6 C5 118.43(2)
C6 C7 C8 120.72(3)
C6 C7 H6 118.2(3)
C8 C7 H6 121.1(3)
C9 C8 C7 121.33(3)
C9 C8 H7 121.2(3)
C7 C8 H7 117.5(3)
C8 C9 C10 119.48(3)
C8 C9 H8 120.0(3)
C10 C9 H8 120.5(3)
C11 C10 C5 117.82(2)
C11 C10 C9 123.33(3)
C5 C10 C9 118.85(2)
C12 C11 C10 120.30(2)
C12 C11 H9 119.9(3)
C10 C11 H9 119.8(3)
C11 C12 C13 119.26(3)
C11 C12 H10 121.1(3)
C13 C12 H10 119.6(3)
N1 C13 C12 120.78(3)
N1 C13 H11 115.2(3)
C12 C13 H11 124.0(3)
C1 O1 H1 110.4(3)
C4 O2 H1 110.6(2)
O3 C1 O1 121.43(3)
O3 C1 C2 119.04(3)
O1 C1 C2 119.53(3)
C3 C2 C1 131.03(3)
C3 C2 H2 117.3(3)
C1 C2 H2 111.7(3)
C2 C3 C4 129.99(2)
C2 C3 H3 116.1(3)
C4 C3 H3 113.8(3)
O4 C4 O2 122.82(2)
O4 C4 C3 116.23(2)
O2 C4 C3 120.94(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O5 C6 1.3412(3)
O5 H5 0.952(6)
N1 C13 1.3286(3)
N1 C5 1.3646(4)
N1 H4 1.046(6)
C5 C10 1.4179(4)
C5 C6 1.4213(4)
C6 C7 1.3811(4)
C7 C8 1.4162(4)
C7 H6 1.093(5)
C8 C9 1.3776(4)
C8 H7 1.084(6)
C9 C10 1.4190(4)
C9 H8 1.086(5)
C10 C11 1.4162(4)
C11 C12 1.3780(4)
C11 H9 1.087(5)
C12 C13 1.3982(4)
C12 H10 1.091(5)
C13 H11 1.079(5)
O1 C1 1.3099(3)
O1 H1 1.041(9)
O2 C4 1.2648(3)
O2 H1 1.404(9)
O3 C1 1.2211(4)
O4 C4 1.2610(4)
C1 C2 1.4969(4)
C2 C3 1.3457(4)
C2 H2 1.087(5)
C3 C4 1.4977(4)
C3 H3 1.084(5)
