#------------------------------------------------------------------------------
#$Date: 2022-03-02 05:20:08 +0200 (Wed, 02 Mar 2022) $
#$Revision: 273207 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/64/1566452.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_1566452
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_absolute_configuration unk
_chemical_formula_moiety         'C9 H8 N O, C4 H3 O4'
_chemical_formula_sum            'C13 H11 N O5'
_chemical_formula_weight         261.236
_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'
_symmetry_Int_Tables_number      19
_audit_creation_date             2021-08-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.3386(1)
_cell_length_b                   9.9878(2)
_cell_length_c                   22.3493(4)
_cell_measurement_reflns_used    100369
_cell_measurement_temperature    15.15
_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_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)'
_diffrn_ambient_temperature      15
_diffrn_measured_fraction_theta_full 0.9984
_diffrn_measured_fraction_theta_max 0.9972
_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 0.9984
_diffrn_reflns_Laue_measured_fraction_max 0.9972
_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 0.9991
_diffrn_reflns_point_group_measured_fraction_max 0.9962
_diffrn_reflns_theta_full        12.2303
_diffrn_reflns_theta_max         24.24
_diffrn_reflns_theta_min         0.91
_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             543.904
_exptl_crystal_size_max          0.119
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.4668
_refine_diff_density_min         -0.4164
_refine_diff_density_rms         0.0672
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.6(13)
_refine_ls_d_res_high            0.4300
_refine_ls_d_res_low             11.1746
_refine_ls_goodness_of_fit_ref   1.5080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     271
_refine_ls_number_reflns         15641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.5080
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0400
_refine_ls_wR_factor_ref         0.0409
_reflns_Friedel_coverage         0.995
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              23
_reflns_limit_k_min              -23
_reflns_limit_l_max              51
_reflns_limit_l_min              -51
_reflns_number_gt                12933
_reflns_number_total             15641
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            fc5060.cif
_cod_data_source_block           HMa-8HQ_NoSpherA2_PBE_ORCA
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               1566452
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All N(H) groups, All O(H) groups
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,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_refinement_flags_posn
O5 O 1.67648(4) 0.21640(3) 0.541804(9) 0.01420(4) Uani 1.000000 .
H5 H 1.7217(14) 0.1734(7) 0.5060(3) 0.0370(18) Uani 1.000000 .
N1 N 1.52244(4) 0.29948(3) 0.649900(10) 0.00977(4) Uani 1.000000 .
H4 H 1.4304(12) 0.3330(6) 0.6115(3) 0.0239(15) Uani 1.000000 .
C5 C 1.71231(5) 0.20834(3) 0.646386(11) 0.00971(4) Uani 1.000000 .
C6 C 1.79203(5) 0.16234(3) 0.589297(11) 0.01128(4) Uani 1.000000 .
C7 C 1.98006(6) 0.06755(3) 0.586763(13) 0.01528(5) Uani 1.000000 .
H6 H 2.0427(11) 0.0334(5) 0.5433(2) 0.0277(13) Uani 1.000000 .
C8 C 2.09170(7) 0.01802(4) 0.639828(14) 0.01687(5) Uani 1.000000 .
H7 H 2.2340(12) -0.0574(6) 0.6355(3) 0.0397(16) Uani 1.000000 .
C9 C 2.02035(6) 0.06445(3) 0.695316(13) 0.01484(5) Uani 1.000000 .
H8 H 2.1114(12) 0.0266(6) 0.7352(3) 0.0347(16) Uani 1.000000 .
C10 C 1.82753(5) 0.16177(3) 0.699628(12) 0.01079(4) Uani 1.000000 .
C11 C 1.74122(6) 0.21443(3) 0.754733(12) 0.01177(4) Uani 1.000000 .
H9 H 1.8260(11) 0.1816(6) 0.7961(2) 0.0335(15) Uani 1.000000 .
C12 C 1.55046(6) 0.30735(3) 0.755713(12) 0.01172(4) Uani 1.000000 .
H10 H 1.4790(11) 0.3467(5) 0.7976(2) 0.0306(14) Uani 1.000000 .
C13 C 1.44213(5) 0.34828(3) 0.701768(12) 0.01090(4) Uani 1.000000 .
H11 H 1.2861(10) 0.4175(5) 0.6986(2) 0.0228(13) Uani 1.000000 .
O1 O 0.64278(5) 0.62232(2) 0.647777(10) 0.01460(4) Uani 1.000000 .
H1 H 0.8018(15) 0.5626(7) 0.6434(3) 0.028(2) Uani 1.000000 .
O2 O 1.01586(4) 0.48359(2) 0.634421(9) 0.01260(4) Uani 1.000000 .
O3 O 0.41198(5) 0.75682(2) 0.592026(10) 0.01710(4) Uani 1.000000 .
O4 O 1.25527(4) 0.41260(2) 0.559787(9) 0.01204(4) Uani 1.000000 .
C1 C 0.58577(6) 0.67796(3) 0.596471(12) 0.01158(4) Uani 1.000000 .
C2 C 0.73567(6) 0.64414(3) 0.541920(12) 0.01121(4) Uani 1.000000 .
H2 H 0.6654(11) 0.6956(6) 0.5030(2) 0.0287(14) Uani 1.000000 .
C3 C 0.93452(6) 0.56298(3) 0.534621(11) 0.01091(4) Uani 1.000000 .
H3 H 1.0109(11) 0.5570(6) 0.4900(2) 0.0269(14) Uani 1.000000 .
C4 C 1.07524(5) 0.48124(3) 0.579638(11) 0.00975(4) Uani 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H -0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C' custom
C -0.00050 0.00030 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C' custom
O 0.00040 0.00130 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C' custom
N -0.00020 0.00070 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C' custom
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
C6 O5 H5 111.8(4) . . ?
C5 N1 H4 121.1(3) . . ?
C13 N1 H4 116.6(3) . . ?
C13 N1 C5 122.32(2) . . ?
C6 C5 N1 119.32(2) . . ?
C10 C5 N1 119.52(2) . . ?
C10 C5 C6 121.15(2) . . ?
C5 C6 O5 116.27(3) . . ?
C7 C6 O5 125.30(2) . . ?
C7 C6 C5 118.43(2) . . ?
H6 C7 C6 118.5(3) . . ?
C8 C7 C6 120.72(3) . . ?
C8 C7 H6 120.8(3) . . ?
H7 C8 C7 117.9(3) . . ?
C9 C8 C7 121.31(3) . . ?
C9 C8 H7 120.8(3) . . ?
H8 C9 C8 119.9(3) . . ?
C10 C9 C8 119.49(3) . . ?
C10 C9 H8 120.6(3) . . ?
C9 C10 C5 118.84(2) . . ?
C11 C10 C5 117.82(3) . . ?
C11 C10 C9 123.33(3) . . ?
H9 C11 C10 119.7(3) . . ?
C12 C11 C10 120.29(2) . . ?
C12 C11 H9 120.0(3) . . ?
H10 C12 C11 121.2(3) . . ?
C13 C12 C11 119.26(3) . . ?
C13 C12 H10 119.5(3) . . ?
C12 C13 N1 120.77(3) . . ?
H11 C13 N1 115.2(3) . . ?
H11 C13 C12 124.0(3) . . ?
C1 O1 H1 110.5(3) . . ?
O2 H1 O1 177.1(5) . . ?
C4 O2 H1 110.7(2) . . ?
O3 C1 O1 121.42(3) . . ?
C2 C1 O1 119.53(3) . . ?
C2 C1 O3 119.04(3) . . ?
H2 C2 C1 111.3(3) . . ?
C3 C2 C1 131.03(3) . . ?
C3 C2 H2 117.7(3) . . ?
H3 C3 C2 116.3(3) . . ?
C4 C3 C2 129.99(2) . . ?
C4 C3 H3 113.6(3) . . ?
O4 C4 O2 122.79(3) . . ?
C3 C4 O2 120.96(3) . . ?
C3 C4 O4 116.25(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
O5 H5 0.939(6) . ?
O5 C6 1.3412(3) . ?
N1 H4 1.044(6) . ?
N1 C5 1.3646(4) . ?
N1 C13 1.3286(3) . ?
C5 C6 1.4213(4) . ?
C5 C10 1.4180(4) . ?
C6 C7 1.3810(4) . ?
C7 H6 1.082(5) . ?
C7 C8 1.4165(4) . ?
C8 H7 1.074(6) . ?
C8 C9 1.3777(4) . ?
C9 H8 1.083(5) . ?
C9 C10 1.4190(4) . ?
C10 C11 1.4162(4) . ?
C11 H9 1.081(5) . ?
C11 C12 1.3780(4) . ?
C12 H10 1.084(5) . ?
C12 C13 1.3982(4) . ?
C13 H11 1.085(5) . ?
O1 H1 1.042(8) . ?
O1 C1 1.3101(3) . ?
H1 O2 1.403(9) . ?
O2 C4 1.2649(3) . ?
O3 C1 1.2211(4) . ?
O4 C4 1.2612(4) . ?
C1 C2 1.4969(4) . ?
C2 H2 1.078(5) . ?
C2 C3 1.3456(4) . ?
C3 H3 1.079(5) . ?
C3 C4 1.4977(4) . ?
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
O5 C6 C5 N1 1.95(3) . . . . ?
O5 C6 C5 C10 -177.69(3) . . . . ?
O5 C6 C7 C8 179.28(3) . . . . ?
N1 C5 C6 C7 -178.36(3) . . . . ?
N1 C5 C10 C9 178.41(3) . . . . ?
N1 C5 C10 C11 -0.95(3) . . . . ?
N1 C13 C12 C11 -0.55(4) . . . . ?
C5 C6 C7 C8 -0.38(4) . . . . ?
C5 C10 C9 C8 0.26(4) . . . . ?
C5 C10 C11 C12 0.31(3) . . . . ?
C6 C7 C8 C9 -1.31(4) . . . . ?
C7 C8 C9 C10 1.35(4) . . . . ?
C8 C9 C10 C11 179.59(3) . . . . ?
C9 C10 C11 C12 -179.02(3) . . . . ?
C10 C11 C12 C13 0.43(4) . . . . ?
O1 C1 C2 C3 -1.00(4) . . . . ?
O2 C4 C3 C2 -1.46(4) . . . . ?
O3 C1 C2 C3 179.22(3) . . . . ?
O4 C4 C3 C2 179.38(3) . . . . ?
C1 C2 C3 C4 -1.41(4) . . . . ?
