#------------------------------------------------------------------------------
#$Date: 2020-06-16 04:24:09 +0300 (Tue, 16 Jun 2020) $
#$Revision: 253165 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/07/7240722.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_7240722
loop_
_publ_author_name
'Malaspina, Lorraine Andrade'
'Hoser, Anna A.'
'Edwards, Alison'
'Woinska, Magdalena'
'Turner, Michael J.'
'Price, Jason R.'
'Sugimoto, Kunihisa'
'Nishibori, Eiji'
'Burgi, Hans-Beat'
'Jayatilaka, Dylan'
'Grabowsky, Simon'
_publ_section_title
;
 Hydrogen atoms in bridging positions from quantum crystallographic
 refinements: Influence of hydrogen atom displacement parameters on
 geometry and electron density
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00378F
_journal_year                    2020
_chemical_absolute_configuration syn
_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_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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     dual
_audit_creation_date             2019-04-29T17:55:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-03-10 deposited with the CCDC.	2020-06-15 downloaded from the CCDC.
;
_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_measurement_wavelength     0.35307
_cell_volume                     1191.68(4)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction
'CrystalClear (Rigaku/MSC Inc., 2006), SORTAV (Blessing, 1995)'
_computing_structure_refinement
'Tonto 18.12.17 github v. 2b3dd9c (Capelli, 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      15(2)
_diffrn_detector                 'SPring-8 BL02B1 Curved Imaging Plate'
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'quarter Χ-circle diffractometer'
_diffrn_measurement_device_type  IPDSC-Q
_diffrn_measurement_method       'phi or omega oscillation scans'
_diffrn_orient_matrix_type       fs_process
_diffrn_orient_matrix_UB_11      0.183986
_diffrn_orient_matrix_UB_12      0.006502
_diffrn_orient_matrix_UB_13      0.007879
_diffrn_orient_matrix_UB_21      -0.024343
_diffrn_orient_matrix_UB_22      0.091336
_diffrn_orient_matrix_UB_23      0.017382
_diffrn_orient_matrix_UB_31      -0.025364
_diffrn_orient_matrix_UB_32      -0.040496
_diffrn_orient_matrix_UB_33      0.04047
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_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
_diffrn_standards_number         0
_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         0.3144
_refine_diff_density_min         -0.2951
_refine_diff_density_rms         0.0473
_refine_ls_abs_structure_details
;
 Flack x determined using 4959 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.6975
_refine_ls_goodness_of_fit_gt    1.6975
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_constraints    66
_refine_ls_number_parameters     205
_refine_ls_number_reflns         12569
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.0057
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.0207
_refine_ls_wR_factor_gt          0.0207
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                12569
_reflns_number_total             15641
_reflns_threshold_expression     'F>0 & F/u(F)>4.0 & |F_calc|>10^-3'
_cod_data_source_file            d0ce00378f2.cif
_cod_data_source_block           8HQ_HAR_neutron
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_Hall     'p 2ac 2ab'
_cod_original_sg_symbol_H-M      'p 21 21 21'
_cod_database_code               7240722
_shelx_estimated_absorpt_t_min   0.995
_shelx_estimated_absorpt_t_max   0.997
_refine_ls_coordinate_system     cartesian
_refine_ls_svd_threshold         0.1E-02
loop_
_symmetry_equiv_pos_as_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_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_disorder_group
C1 0.58580(6) 0.67792(3) 0.596512(13) 0.01173(12) Uani 1 0
C2 0.73554(6) 0.64408(3) 0.541921(13) 0.01136(11) Uani 1 0
C3 0.93464(6) 0.56292(3) 0.534640(13) 0.01113(12) Uani 1 0
C4 1.07532(6) 0.48126(3) 0.579637(12) 0.00992(11) Uani 1 0
C6 0.79190(6) 0.16236(3) 0.589282(13) 0.01156(12) Uani 1 0
C7 0.98022(7) 0.06751(4) 0.586769(14) 0.01547(14) Uani 1 0
C8 1.09172(7) 0.01802(4) 0.639815(15) 0.01711(14) Uani 1 0
C9 1.02023(7) 0.06442(4) 0.695349(15) 0.01510(14) Uani 1 0
C10 0.82756(6) 0.16175(3) 0.699636(13) 0.01096(11) Uani 1 0
C5 0.71218(6) 0.20837(3) 0.646393(13) 0.00992(11) Uani 1 0
C13 0.44209(6) 0.34827(3) 0.701760(13) 0.01113(11) Uani 1 0
C12 0.55043(6) 0.30736(3) 0.755731(13) 0.01186(12) Uani 1 0
C11 0.74137(7) 0.21442(3) 0.754731(13) 0.01202(11) Uani 1 0
N1 0.52240(5) 0.29949(3) 0.649870(11) 0.00981(10) Uani 1 0
O5 0.67659(5) 0.21631(3) 0.541753(10) 0.01416(10) Uani 1 0
O4 1.25526(5) 0.41266(2) 0.559762(10) 0.01202(9) Uani 1 0
O2 1.01598(5) 0.48365(3) 0.634425(10) 0.01266(10) Uani 1 0
O3 0.41184(5) 0.75672(3) 0.592038(11) 0.01713(11) Uani 1 0
O1 0.64305(5) 0.62230(3) 0.647781(10) 0.01462(10) Uani 1 0
H8 1.1135(12) 0.0272(6) 0.7357(2) 0.02506667 Uani 1 0
H7 1.2380(12) -0.0595(6) 0.6357(3) 0.02656667 Uani 1 0
H6 1.0472(11) 0.0323(6) 0.5441(2) 0.0256 Uani 1 0
H5 0.7293(14) 0.1681(7) 0.5043(3) 0.0214 Uani 1 0
H4 0.4283(13) 0.3356(7) 0.6102(3) 0.0187 Uani 1 0
H9 0.8265(11) 0.1795(6) 0.7960(2) 0.0235333 Uani 1 0
H10 0.4785(11) 0.3467(5) 0.7977(2) 0.0225333 Uani 1 0
H11 0.2822(11) 0.4165(5) 0.6986(3) 0.0222333 Uani 1 0
H1 0.8089(16) 0.5610(8) 0.6438(3) 0.0190333 Uani 1 0
H2 0.6690(11) 0.6980(6) 0.5018(2) 0.0231 Uani 1 0
H3 1.0136(12) 0.5580(6) 0.4897(2) 0.0215667 Uani 1 0
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'
H H 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'
N N 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'
O O 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'
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
O4 C4 O2 122.82(3) . . . yes
O3 C1 O1 121.49(3) . . . yes
O5 C6 C7 125.25(3) . . . yes
O5 C6 C5 116.36(3) . . . yes
O4 C4 C3 116.21(3) . . . yes
O2 C4 C3 120.96(3) . . . yes
O3 C1 C2 118.99(3) . . . yes
O1 C1 C2 119.51(3) . . . yes
N1 C5 C6 119.28(3) . . . yes
N1 C5 C10 119.59(3) . . . yes
N1 C13 C12 120.80(3) . . . yes
N1 C13 H11 115.0(3) . . . yes
C1 O1 H1 111.1(4) . . . yes
C6 O5 H5 109.8(4) . . . yes
C5 N1 C13 122.27(3) . . . yes
C5 N1 H4 121.4(3) . . . yes
C13 N1 H4 116.3(3) . . . yes
C1 C2 C3 130.98(3) . . . yes
C2 C3 C4 130.00(3) . . . yes
C6 C7 C8 120.73(3) . . . yes
C6 C5 C10 121.13(3) . . . yes
C7 C6 C5 118.40(3) . . . yes
C7 C8 C9 121.34(3) . . . yes
C8 C9 C10 119.46(3) . . . yes
C9 C10 C5 118.89(3) . . . yes
C9 C10 C11 123.30(3) . . . yes
C10 C11 C12 120.30(3) . . . yes
C5 C10 C11 117.80(3) . . . yes
C13 C12 C11 119.23(3) . . . yes
C1 C2 H2 112.3(3) . . . yes
C2 C3 H3 116.3(3) . . . yes
C3 C2 H2 116.7(3) . . . yes
C4 C3 H3 113.6(3) . . . yes
C6 C7 H6 120.0(3) . . . yes
C7 C8 H7 118.2(3) . . . yes
C8 C7 H6 119.2(3) . . . yes
C8 C9 H8 120.1(3) . . . yes
C9 C8 H7 120.5(3) . . . yes
C10 C9 H8 120.4(3) . . . yes
C10 C11 H9 118.9(3) . . . yes
C13 C12 H10 119.5(3) . . . yes
C12 C13 H11 124.1(3) . . . yes
C12 C11 H9 120.8(3) . . . yes
C11 C12 H10 121.3(3) . . . yes
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
O5 C6 1.3407(4) . . yes
O4 C4 1.2608(4) . . yes
O2 C4 1.2650(4) . . yes
O3 C1 1.2215(4) . . yes
O1 C1 1.3095(4) . . yes
O5 H5 1.006(6) . . yes
O1 H1 1.080(9) . . yes
N1 C5 1.3641(4) . . yes
N1 C13 1.3289(4) . . yes
N1 H4 1.082(6) . . yes
C1 C2 1.4973(4) . . yes
C2 C3 1.3466(5) . . yes
C3 C4 1.4968(4) . . yes
C6 C7 1.3826(5) . . yes
C6 C5 1.4218(4) . . yes
C7 C8 1.4157(5) . . yes
C8 C9 1.3787(5) . . yes
C9 C10 1.4185(5) . . yes
C10 C5 1.4185(4) . . yes
C10 C11 1.4159(4) . . yes
C13 C12 1.3987(4) . . yes
C12 C11 1.3789(5) . . yes
C2 H2 1.104(5) . . yes
C3 H3 1.090(5) . . yes
C7 H6 1.078(5) . . yes
C8 H7 1.104(6) . . yes
C9 H8 1.096(5) . . yes
C13 H11 1.095(5) . . yes
C12 H10 1.086(5) . . yes
C11 H9 1.085(5) . . yes
