# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_NPTL
_database_code_depnum_ccdc_archive 'CCDC 2088222'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2021-06-05 deposited with the CCDC.	2022-06-15 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C10 H8 O'
_chemical_formula_moiety         'C10 H8 O'
_chemical_formula_weight         144.17
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
_space_group_IT_number           9
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 +X,-Y,1/2+Z
3 1/2+X,1/2+Y,+Z
4 1/2+X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   32.026(14)
_cell_length_b                   5.919(2)
_cell_length_c                   8.120(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 101.288(9)
_cell_angle_gamma                90.0000
_cell_volume                     1509.5(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1692
_cell_measurement_theta_min      3.50
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    295
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608.00
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.994

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      295
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            6356
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         3.503
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_point_group_measured_fraction_full 0.870
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2958
_reflns_number_gt                2012
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_max     0.716
_reflns_Friedel_fraction_full    0.754

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1512
_refine_ls_wR_factor_gt          0.1286
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2958
_refine_ls_number_parameters     208
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0695P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.14
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0063(15)
_refine_ls_abs_structure_details 
;
 Flack x determined using 702 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.2(10)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC 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_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 0.04387(13) 0.2964(6) 0.2362(4) 0.0857(10) Uani 1 1 d . . . . .
O2 O 0.01296(13) 0.6452(7) 0.4002(5) 0.0948(11) Uani 1 1 d . . . . .
C1 C 0.11064(13) 0.4014(7) 0.4079(4) 0.0532(10) Uani 1 1 d . . . . .
H1 H 0.099127 0.536733 0.436542 0.064 Uiso 1 1 calc R U . . .
C2 C 0.08612(15) 0.2555(7) 0.3029(4) 0.0606(12) Uani 1 1 d . . . . .
C3 C 0.10261(15) 0.0499(7) 0.2562(5) 0.0636(12) Uani 1 1 d . . . . .
H2 H 0.085436 -0.048023 0.182918 0.076 Uiso 1 1 calc R U . . .
C4 C 0.14382(14) -0.0038(5) 0.3193(5) 0.0567(11) Uani 1 1 d . . . . .
H3 H 0.154546 -0.140541 0.289299 0.068 Uiso 1 1 calc R U . . .
C5 C 0.17084(13) 0.1426(6) 0.4293(5) 0.0493(11) Uani 1 1 d . . . . .
C6 C 0.21355(15) 0.0910(7) 0.4966(5) 0.0598(11) Uani 1 1 d . . . . .
H4 H 0.225005 -0.044309 0.467680 0.072 Uiso 1 1 calc R U . . .
C7 C 0.23845(15) 0.2354(8) 0.6032(6) 0.0674(13) Uani 1 1 d . . . . .
H5 H 0.266658 0.198246 0.646932 0.081 Uiso 1 1 calc R U . . .
C8 C 0.22176(15) 0.4390(7) 0.6472(5) 0.0640(11) Uani 1 1 d . . . . .
H6 H 0.238989 0.537203 0.720051 0.077 Uiso 1 1 calc R U . . .
C9 C 0.18061(13) 0.4956(6) 0.5848(5) 0.0550(10) Uani 1 1 d . . . . .
H7 H 0.170069 0.632622 0.615125 0.066 Uiso 1 1 calc R U . . .
C10 C 0.15353(14) 0.3492(5) 0.4742(4) 0.0453(10) Uani 1 1 d . . . . .
C11 C -0.05433(13) 0.5788(7) 0.2283(5) 0.0555(11) Uani 1 1 d . . . . .
H9 H -0.044072 0.441684 0.196801 0.067 Uiso 1 1 calc R U . . .
C12 C -0.02822(14) 0.7165(8) 0.3391(5) 0.0607(12) Uani 1 1 d . . . . .
C13 C -0.04276(15) 0.9220(8) 0.3874(5) 0.0650(12) Uani 1 1 d . . . . .
H10 H -0.024700 1.013771 0.462668 0.078 Uiso 1 1 calc R U . . .
C14 C -0.08333(14) 0.9899(6) 0.3251(5) 0.0584(11) Uani 1 1 d . . . . .
H11 H -0.092757 1.128140 0.358127 0.070 Uiso 1 1 calc R U . . .
C15 C -0.11135(13) 0.8532(6) 0.2108(5) 0.0464(10) Uani 1 1 d . . . . .
C16 C -0.15390(14) 0.9165(7) 0.1448(5) 0.0597(11) Uani 1 1 d . . . . .
H12 H -0.164097 1.053876 0.176001 0.072 Uiso 1 1 calc R U . . .
C17 C -0.18014(16) 0.7797(8) 0.0364(6) 0.0669(13) Uani 1 1 d . . . . .
H13 H -0.208084 0.823470 -0.005577 0.080 Uiso 1 1 calc R U . . .
C18 C -0.16505(16) 0.5720(8) -0.0121(6) 0.0666(12) Uani 1 1 d . . . . .
H14 H -0.183060 0.479190 -0.086747 0.080 Uiso 1 1 calc R U . . .
C19 C -0.12444(13) 0.5058(6) 0.0490(5) 0.0528(10) Uani 1 1 d . . . . .
H15 H -0.114944 0.367782 0.015764 0.063 Uiso 1 1 calc R U . . .
C20 C -0.09636(13) 0.6431(6) 0.1621(5) 0.0468(11) Uani 1 1 d . . . . .
H8 H 0.035(3) 0.436(15) 0.296(13) 0.22(4) Uiso 1 1 d . . . . .
H16 H 0.027(3) 0.711(11) 0.507(11) 0.22(4) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_structure_solution    'SIR2002 (Burla, et al., 2003)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C2 1.377(6) . ?
O1 H8 1.02(8) . ?
O2 C12 1.381(6) . ?
O2 H16 0.97(8) . ?
C1 C2 1.352(5) . ?
C1 C10 1.408(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.408(6) . ?
C3 C4 1.357(6) . ?
C3 H2 0.9300 . ?
C4 C5 1.413(5) . ?
C4 H3 0.9300 . ?
C5 C6 1.404(6) . ?
C5 C10 1.420(4) . ?
C6 C7 1.358(7) . ?
C6 H4 0.9300 . ?
C7 C8 1.393(7) . ?
C7 H5 0.9300 . ?
C8 C9 1.358(6) . ?
C8 H6 0.9300 . ?
C9 C10 1.416(5) . ?
C9 H7 0.9300 . ?
C11 C12 1.371(6) . ?
C11 C20 1.401(6) . ?
C11 H9 0.9300 . ?
C12 C13 1.386(7) . ?
C13 C14 1.359(6) . ?
C13 H10 0.9300 . ?
C14 C15 1.412(6) . ?
C14 H11 0.9300 . ?
C15 C16 1.414(6) . ?
C15 C20 1.417(4) . ?
C16 C17 1.359(6) . ?
C16 H12 0.9300 . ?
C17 C18 1.405(7) . ?
C17 H13 0.9300 . ?
C18 C19 1.356(6) . ?
C18 H14 0.9300 . ?
C19 C20 1.411(5) . ?
C19 H15 0.9300 . ?

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
C2 O1 H8 107(5) . . ?
C12 O2 H16 115(6) . . ?
C2 C1 C10 120.2(3) . . ?
C2 C1 H1 119.9 . . ?
C10 C1 H1 119.9 . . ?
C1 C2 O1 122.7(4) . . ?
C1 C2 C3 121.3(4) . . ?
O1 C2 C3 116.0(4) . . ?
C4 C3 C2 119.3(4) . . ?
C4 C3 H2 120.3 . . ?
C2 C3 H2 120.3 . . ?
C3 C4 C5 121.7(4) . . ?
C3 C4 H3 119.2 . . ?
C5 C4 H3 119.2 . . ?
C6 C5 C4 122.8(4) . . ?
C6 C5 C10 119.1(3) . . ?
C4 C5 C10 118.0(3) . . ?
C7 C6 C5 121.1(4) . . ?
C7 C6 H4 119.4 . . ?
C5 C6 H4 119.4 . . ?
C6 C7 C8 120.1(4) . . ?
C6 C7 H5 120.0 . . ?
C8 C7 H5 120.0 . . ?
C9 C8 C7 120.7(4) . . ?
C9 C8 H6 119.6 . . ?
C7 C8 H6 119.6 . . ?
C8 C9 C10 121.0(4) . . ?
C8 C9 H7 119.5 . . ?
C10 C9 H7 119.5 . . ?
C1 C10 C9 122.6(3) . . ?
C1 C10 C5 119.4(3) . . ?
C9 C10 C5 118.0(4) . . ?
C12 C11 C20 120.5(3) . . ?
C12 C11 H9 119.8 . . ?
C20 C11 H9 119.8 . . ?
C11 C12 O2 118.1(4) . . ?
C11 C12 C13 120.8(4) . . ?
O2 C12 C13 121.1(4) . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 H10 119.9 . . ?
C12 C13 H10 119.9 . . ?
C13 C14 C15 120.9(4) . . ?
C13 C14 H11 119.6 . . ?
C15 C14 H11 119.6 . . ?
C14 C15 C16 122.6(3) . . ?
C14 C15 C20 118.6(3) . . ?
C16 C15 C20 118.7(3) . . ?
C17 C16 C15 121.1(4) . . ?
C17 C16 H12 119.5 . . ?
C15 C16 H12 119.5 . . ?
C16 C17 C18 120.0(4) . . ?
C16 C17 H13 120.0 . . ?
C18 C17 H13 120.0 . . ?
C19 C18 C17 120.5(4) . . ?
C19 C18 H14 119.7 . . ?
C17 C18 H14 119.7 . . ?
C18 C19 C20 121.0(4) . . ?
C18 C19 H15 119.5 . . ?
C20 C19 H15 119.5 . . ?
C11 C20 C19 122.4(4) . . ?
C11 C20 C15 119.0(3) . . ?
C19 C20 C15 118.7(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
C10 C1 C2 O1 179.1(4) . . . . ?
C10 C1 C2 C3 -0.4(6) . . . . ?
C1 C2 C3 C4 0.7(6) . . . . ?
O1 C2 C3 C4 -178.9(4) . . . . ?
C2 C3 C4 C5 -0.8(6) . . . . ?
C3 C4 C5 C6 179.9(3) . . . . ?
C3 C4 C5 C10 0.6(6) . . . . ?
C4 C5 C6 C7 -179.4(4) . . . . ?
C10 C5 C6 C7 -0.1(6) . . . . ?
C5 C6 C7 C8 -0.2(7) . . . . ?
C6 C7 C8 C9 0.1(7) . . . . ?
C7 C8 C9 C10 0.3(6) . . . . ?
C2 C1 C10 C9 -179.9(4) . . . . ?
C2 C1 C10 C5 0.2(5) . . . . ?
C8 C9 C10 C1 179.5(3) . . . . ?
C8 C9 C10 C5 -0.6(6) . . . . ?
C6 C5 C10 C1 -179.6(4) . . . . ?
C4 C5 C10 C1 -0.3(5) . . . . ?
C6 C5 C10 C9 0.6(5) . . . . ?
C4 C5 C10 C9 179.9(4) . . . . ?
C20 C11 C12 O2 -179.8(4) . . . . ?
C20 C11 C12 C13 -0.2(7) . . . . ?
C11 C12 C13 C14 0.0(7) . . . . ?
O2 C12 C13 C14 179.6(4) . . . . ?
C12 C13 C14 C15 0.1(6) . . . . ?
C13 C14 C15 C16 179.2(3) . . . . ?
C13 C14 C15 C20 0.0(6) . . . . ?
C14 C15 C16 C17 -179.3(4) . . . . ?
C20 C15 C16 C17 -0.1(6) . . . . ?
C15 C16 C17 C18 -0.2(6) . . . . ?
C16 C17 C18 C19 0.3(7) . . . . ?
C17 C18 C19 C20 -0.1(7) . . . . ?
C12 C11 C20 C19 -179.4(4) . . . . ?
C12 C11 C20 C15 0.4(6) . . . . ?
C18 C19 C20 C11 179.6(4) . . . . ?
C18 C19 C20 C15 -0.2(6) . . . . ?
C14 C15 C20 C11 -0.3(5) . . . . ?
C16 C15 C20 C11 -179.5(4) . . . . ?
C14 C15 C20 C19 179.5(4) . . . . ?
C16 C15 C20 C19 0.3(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H8 O2 . . . 2.744(6) 1.02(10) 1.73(10) 170(8) no
O2 H16 O1 . . 2_565 2.736(5) 0.97(8) 1.84(8) 152(7) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        2-Naphthol
_exptl_crystal_recrystallization_method Sublimation
####################################################################### 
# 
# 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_DHBA-d3-Form-I
_database_code_depnum_ccdc_archive 'CCDC 2088221'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2021-08-10 deposited with the CCDC.	2022-06-15 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C7 H6 O4'
_chemical_formula_moiety         'C7 H6 O4'
_chemical_formula_weight         154.12
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
_space_group_IT_number           7
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 +X,-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   4.9736(9)
_cell_length_b                   11.826(3)
_cell_length_c                   11.220(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.477(5)
_cell_angle_gamma                90.0000
_cell_volume                     659.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2366
_cell_measurement_theta_min      3.45
_cell_measurement_theta_max      27.49
_cell_measurement_temperature    295
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320.00
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_T_max  0.981

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      295
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            5515
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         3.446
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_point_group_measured_fraction_full 0.914
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2660
_reflns_number_gt                2331
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_max     0.762
_reflns_Friedel_fraction_full    0.836

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1421
_refine_ls_wR_factor_gt          0.1265
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2660
_refine_ls_number_parameters     224
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0797P)²+0.0081P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.19
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.091(16)
_refine_ls_abs_structure_details 
;
 Flack x determined using 841 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.3(10)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC 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_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 0.6035(6) 0.6121(3) 0.4886(3) 0.0458(7) Uani 1 1 d . . . . .
O2 O 0.6972(5) 0.7431(2) 0.3526(2) 0.0466(7) Uani 1 1 d . . . . .
O3 O 1.0893(6) 0.7075(3) 0.2015(3) 0.0528(8) Uani 1 1 d . . . . .
O4 O 1.1963(7) 0.2874(3) 0.4105(3) 0.0566(9) Uani 1 1 d . . . . .
O5 O 0.3106(6) 0.8889(2) 0.4104(2) 0.0457(8) Uani 1 1 d . . . . .
O6 O 0.2170(5) 0.7602(2) 0.5487(2) 0.0445(7) Uani 1 1 d . . . . .
O7 O -0.1720(7) 0.8004(3) 0.7006(3) 0.0624(10) Uani 1 1 d . . . . .
O8 O -0.3063(6) 1.2117(3) 0.4780(3) 0.0610(10) Uani 1 1 d . . . . .
C1 C 0.7398(7) 0.6501(3) 0.3974(3) 0.0350(7) Uani 1 1 d . . . . .
C2 C 0.9483(8) 0.5726(3) 0.3524(3) 0.0339(7) Uani 1 1 d . . . . .
C3 C 1.1092(8) 0.6062(3) 0.2563(3) 0.0389(9) Uani 1 1 d . . . . .
C4 C 1.3055(8) 0.5319(3) 0.2152(3) 0.0432(9) Uani 1 1 d . . . . .
H4 H 1.414878 0.553460 0.152285 0.052 Uiso 1 1 calc R U . . .
C5 C 1.3391(8) 0.4266(4) 0.2668(4) 0.0418(9) Uani 1 1 d . . . . .
H5 H 1.469558 0.377409 0.238391 0.050 Uiso 1 1 calc R U . . .
C6 C 1.1766(8) 0.3944(3) 0.3618(4) 0.0390(9) Uani 1 1 d . . . . .
C7 C 0.9856(7) 0.4667(3) 0.4048(3) 0.0375(8) Uani 1 1 d . . . . .
H6 H 0.880468 0.445135 0.469061 0.045 Uiso 1 1 calc R U . . .
C8 C 0.1720(8) 0.8533(3) 0.5022(3) 0.0362(8) Uani 1 1 d . . . . .
C9 C -0.0337(8) 0.9301(3) 0.5453(3) 0.0348(7) Uani 1 1 d . . . . .
C10 C -0.1963(8) 0.9005(3) 0.6423(4) 0.0393(9) Uani 1 1 d . . . . .
C11 C -0.3896(8) 0.9760(4) 0.6813(3) 0.0461(10) Uani 1 1 d . . . . .
H10 H -0.496319 0.956972 0.745928 0.055 Uiso 1 1 calc R U . . .
C12 C -0.4258(8) 1.0781(3) 0.6261(4) 0.0426(9) Uani 1 1 d . . . . .
H11 H -0.557378 1.127500 0.653084 0.051 Uiso 1 1 calc R U . . .
C13 C -0.2676(8) 1.1082(3) 0.5303(4) 0.0397(9) Uani 1 1 d . . . . .
C14 C -0.0737(8) 1.0347(3) 0.4902(3) 0.0382(8) Uani 1 1 d . . . . .
H12 H 0.031898 1.054961 0.425565 0.046 Uiso 1 1 calc R U . . .
H1 H 0.490(9) 0.668(3) 0.506(4) 0.042(10) Uiso 1 1 d . . . . .
H2 H 0.971(17) 0.766(6) 0.266(7) 0.14(3) Uiso 1 1 d . . . . .
H3 H 1.371(11) 0.264(4) 0.422(5) 0.086(16) Uiso 1 1 d . . . . .
H7 H 0.481(13) 0.829(5) 0.389(5) 0.087(18) Uiso 1 1 d . . . . .
H8 H -0.026(9) 0.768(4) 0.670(4) 0.049(11) Uiso 1 1 d . . . . .
H9 H -0.151(13) 1.235(5) 0.436(7) 0.13(2) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C1 1.311(5) . ?
O1 H1 0.90(4) . ?
O2 C1 1.227(4) . ?
O3 C3 1.351(5) . ?
O3 H2 1.17(8) . ?
O4 C6 1.382(5) . ?
O4 H3 0.92(5) . ?
O5 C8 1.313(5) . ?
O5 H7 1.13(6) . ?
O6 C8 1.238(5) . ?
O7 C10 1.358(5) . ?
O7 H8 0.89(5) . ?
O8 C13 1.371(5) . ?
O8 H9 0.95(7) . ?
C1 C2 1.477(5) . ?
C2 C7 1.395(5) . ?
C2 C3 1.405(6) . ?
C3 C4 1.394(6) . ?
C4 C5 1.384(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.368(6) . ?
C7 H6 0.9300 . ?
C8 C9 1.454(5) . ?
C9 C14 1.396(5) . ?
C9 C10 1.406(6) . ?
C10 C11 1.385(6) . ?
C11 C12 1.368(6) . ?
C11 H10 0.9300 . ?
C12 C13 1.384(6) . ?
C12 H11 0.9300 . ?
C13 C14 1.377(6) . ?
C14 H12 0.9300 . ?

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
C1 O1 H1 104(3) . . ?
C3 O3 H2 106(4) . . ?
C6 O4 H3 113(3) . . ?
C8 O5 H7 111(3) . . ?
C10 O7 H8 105(3) . . ?
C13 O8 H9 111(4) . . ?
O2 C1 O1 122.6(4) . . ?
O2 C1 C2 122.4(3) . . ?
O1 C1 C2 115.0(3) . . ?
C7 C2 C3 120.2(3) . . ?
C7 C2 C1 120.3(3) . . ?
C3 C2 C1 119.5(3) . . ?
O3 C3 C4 117.2(4) . . ?
O3 C3 C2 124.1(4) . . ?
C4 C3 C2 118.7(4) . . ?
C5 C4 C3 120.7(4) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 O4 118.7(4) . . ?
C7 C6 C5 120.5(3) . . ?
O4 C6 C5 120.8(4) . . ?
C6 C7 C2 120.2(4) . . ?
C6 C7 H6 119.9 . . ?
C2 C7 H6 119.9 . . ?
O6 C8 O5 121.5(4) . . ?
O6 C8 C9 122.7(3) . . ?
O5 C8 C9 115.8(3) . . ?
C14 C9 C10 118.8(4) . . ?
C14 C9 C8 120.3(4) . . ?
C10 C9 C8 120.9(3) . . ?
O7 C10 C11 118.0(4) . . ?
O7 C10 C9 122.7(4) . . ?
C11 C10 C9 119.3(4) . . ?
C12 C11 C10 121.0(4) . . ?
C12 C11 H10 119.5 . . ?
C10 C11 H10 119.5 . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H11 119.8 . . ?
C13 C12 H11 119.8 . . ?
O8 C13 C14 121.3(4) . . ?
O8 C13 C12 118.9(4) . . ?
C14 C13 C12 119.7(3) . . ?
C13 C14 C9 120.8(4) . . ?
C13 C14 H12 119.6 . . ?
C9 C14 H12 119.6 . . ?

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
O2 C1 C2 C7 -178.7(4) . . . . ?
O1 C1 C2 C7 1.2(5) . . . . ?
O2 C1 C2 C3 1.3(5) . . . . ?
O1 C1 C2 C3 -178.8(4) . . . . ?
C7 C2 C3 O3 -179.1(4) . . . . ?
C1 C2 C3 O3 0.9(6) . . . . ?
C7 C2 C3 C4 -0.1(5) . . . . ?
C1 C2 C3 C4 179.9(4) . . . . ?
O3 C3 C4 C5 179.8(3) . . . . ?
C2 C3 C4 C5 0.8(6) . . . . ?
C3 C4 C5 C6 -0.5(6) . . . . ?
C4 C5 C6 C7 -0.5(6) . . . . ?
C4 C5 C6 O4 176.4(4) . . . . ?
O4 C6 C7 C2 -175.8(3) . . . . ?
C5 C6 C7 C2 1.2(6) . . . . ?
C3 C2 C7 C6 -0.9(5) . . . . ?
C1 C2 C7 C6 179.1(4) . . . . ?
O6 C8 C9 C14 179.3(4) . . . . ?
O5 C8 C9 C14 -0.3(5) . . . . ?
O6 C8 C9 C10 -1.1(6) . . . . ?
O5 C8 C9 C10 179.4(3) . . . . ?
C14 C9 C10 O7 179.7(4) . . . . ?
C8 C9 C10 O7 0.0(6) . . . . ?
C14 C9 C10 C11 -0.6(6) . . . . ?
C8 C9 C10 C11 179.7(4) . . . . ?
O7 C10 C11 C12 -179.6(4) . . . . ?
C9 C10 C11 C12 0.6(6) . . . . ?
C10 C11 C12 C13 -0.5(6) . . . . ?
C11 C12 C13 O8 -179.1(4) . . . . ?
C11 C12 C13 C14 0.3(6) . . . . ?
O8 C13 C14 C9 179.1(4) . . . . ?
C12 C13 C14 C9 -0.3(6) . . . . ?
C10 C9 C14 C13 0.4(5) . . . . ?
C8 C9 C14 C13 -179.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 O6 . . . 2.690(4) 0.90(4) 1.81(4) 169(4) no
O3 H2 O2 . . . 2.629(4) 1.17(8) 1.70(8) 132(6) no
O4 H3 O8 . . 1_745 2.732(5) 0.92(5) 1.82(6) 168(6) no
O5 H7 O2 . . . 2.667(4) 1.13(6) 1.54(6) 175(5) no
O7 H8 O6 . . . 2.632(4) 0.89(4) 1.83(4) 148(4) no
O8 H9 O4 . . 1_465 2.767(5) 0.95(7) 1.86(7) 159(7) no

#==============================================================================
# start Validation Reply Form
_vrf_PLAT355_DHBA-d3-Form-I      
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O3       - H2       .       1.16 Ang.  
RESPONSE: The refined positions of these hydrogen atoms have large 
ambiguity due to the artifacts of pseudo-inversion symmetry locating on 
the carboxylic acid dimer.
;
_vrf_PLAT111_DHBA-d3-Form-I      
;
PROBLEM: ADDSYM Detects New (Pseudo) Centre of Symmetry .        100 %Fit  
RESPONSE: ...
;
_vrf_PLAT113_DHBA-d3-Form-I      
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group      P21/c Check 
RESPONSE: The existence of pseudo-symmetry is esssential observation for
 ferroelectric compounds.
;
# end Validation Reply Form

# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        '2,5-Dihydroxybenzoic acid-deuterated'
_exptl_crystal_recrystallization_method Sublimation
_exptl_crystal_preparation       ferroelectric
####################################################################### 
# 
# 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_DHBA-Form-I
_database_code_depnum_ccdc_archive 'CCDC 2088220'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2021-08-10 deposited with the CCDC.	2022-06-15 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C7 H6 O4'
_chemical_formula_moiety         'C7 H6 O4'
_chemical_formula_weight         154.12
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
_space_group_IT_number           7
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 +X,-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   4.9705(12)
_cell_length_b                   11.838(3)
_cell_length_c                   11.248(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.405(6)
_cell_angle_gamma                90.0000
_cell_volume                     661.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2020
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.190
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320.00
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_T_max  0.976

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            6426
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_theta_max         27.471
_diffrn_reflns_theta_min         3.442
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_point_group_measured_fraction_full 0.907
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2686
_reflns_number_gt                2279
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_max     0.773
_reflns_Friedel_fraction_full    0.820

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1403
_refine_ls_wR_factor_gt          0.1305
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2686
_refine_ls_number_parameters     224
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0826P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.033(9)
_refine_ls_abs_structure_details 
;
 Flack x determined using 753 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(10)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC 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_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 0.6006(7) 0.6129(2) 0.6600(3) 0.0453(8) Uani 1 1 d . . . . .
O2 O 0.6952(5) 0.7436(2) 0.5236(2) 0.0463(7) Uani 1 1 d . . . . .
O3 O 1.0862(7) 0.7078(3) 0.3722(3) 0.0547(8) Uani 1 1 d . . . . .
O4 O 1.1937(7) 0.2874(2) 0.5814(3) 0.0550(9) Uani 1 1 d . . . . .
O5 O 0.3084(7) 0.8890(2) 0.5819(3) 0.0457(8) Uani 1 1 d . . . . .
O6 O 0.2155(5) 0.7601(2) 0.7199(2) 0.0444(7) Uani 1 1 d . . . . .
O7 O -0.1743(7) 0.8005(3) 0.8719(3) 0.0606(10) Uani 1 1 d . . . . .
O8 O -0.3095(6) 1.2116(3) 0.6489(4) 0.0611(10) Uani 1 1 d . . . . .
C1 C 0.7379(7) 0.6502(3) 0.5689(4) 0.0349(8) Uani 1 1 d . . . . .
C2 C 0.9454(8) 0.5734(3) 0.5233(4) 0.0343(8) Uani 1 1 d . . . . .
C3 C 1.1067(9) 0.6059(3) 0.4274(4) 0.0389(9) Uani 1 1 d . . . . .
C4 C 1.3024(9) 0.5317(4) 0.3856(4) 0.0454(10) Uani 1 1 d . . . . .
H4 H 1.410235 0.552788 0.322104 0.055 Uiso 1 1 calc R U . . .
C5 C 1.3371(8) 0.4274(3) 0.4375(4) 0.0419(10) Uani 1 1 d . . . . .
H5 H 1.468573 0.378523 0.409355 0.050 Uiso 1 1 calc R U . . .
C6 C 1.1750(9) 0.3948(3) 0.5327(4) 0.0378(9) Uani 1 1 d . . . . .
C7 C 0.9845(8) 0.4677(3) 0.5760(3) 0.0368(8) Uani 1 1 d . . . . .
H6 H 0.880818 0.446671 0.640877 0.044 Uiso 1 1 calc R U . . .
C8 C 0.1715(7) 0.8531(3) 0.6735(3) 0.0350(8) Uani 1 1 d . . . . .
C9 C -0.0367(8) 0.9305(3) 0.7158(4) 0.0342(8) Uani 1 1 d . . . . .
C10 C -0.1990(9) 0.9002(3) 0.8127(4) 0.0385(9) Uani 1 1 d . . . . .
C11 C -0.3939(8) 0.9755(4) 0.8527(4) 0.0440(10) Uani 1 1 d . . . . .
H10 H -0.501412 0.956351 0.916942 0.053 Uiso 1 1 calc R U . . .
C12 C -0.4276(9) 1.0788(3) 0.7967(4) 0.0414(10) Uani 1 1 d . . . . .
H11 H -0.558231 1.128622 0.823741 0.050 Uiso 1 1 calc R U . . .
C13 C -0.2694(9) 1.1087(3) 0.7011(4) 0.0408(10) Uani 1 1 d . . . . .
C14 C -0.0747(8) 1.0356(3) 0.6609(4) 0.0377(8) Uani 1 1 d . . . . .
H12 H 0.032152 1.056110 0.596905 0.045 Uiso 1 1 calc R U . . .
H1 H 0.472(9) 0.662(4) 0.679(4) 0.043(11) Uiso 1 1 d . . . . .
H2 H 0.981(17) 0.771(6) 0.438(8) 0.15(3) Uiso 1 1 d . . . . .
H3 H 1.372(11) 0.265(4) 0.584(5) 0.079(15) Uiso 1 1 d . . . . .
H7 H 0.449(14) 0.816(5) 0.564(6) 0.10(2) Uiso 1 1 d . . . . .
H8 H -0.017(10) 0.766(4) 0.836(4) 0.056(12) Uiso 1 1 d . . . . .
H9 H -0.160(14) 1.232(5) 0.616(7) 0.12(2) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_structure_solution    'SIR2002 (Burla, et al., 2003)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C1 1.312(5) . ?
O1 H1 0.89(5) . ?
O2 C1 1.236(5) . ?
O3 C3 1.360(5) . ?
O3 H2 1.18(9) . ?
O4 C6 1.387(5) . ?
O4 H3 0.93(5) . ?
O5 C8 1.309(5) . ?
O5 H7 1.13(7) . ?
O6 C8 1.237(5) . ?
O7 C10 1.361(5) . ?
O7 H8 0.97(5) . ?
O8 C13 1.367(5) . ?
O8 H9 0.86(7) . ?
C1 C2 1.470(5) . ?
C2 C7 1.397(5) . ?
C2 C3 1.403(6) . ?
C3 C4 1.395(6) . ?
C4 C5 1.376(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.374(6) . ?
C7 H6 0.9300 . ?
C8 C9 1.465(5) . ?
C9 C14 1.401(5) . ?
C9 C10 1.407(6) . ?
C10 C11 1.393(6) . ?
C11 C12 1.385(6) . ?
C11 H10 0.9300 . ?
C12 C13 1.382(7) . ?
C12 H11 0.9300 . ?
C13 C14 1.377(6) . ?
C14 H12 0.9300 . ?

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
C1 O1 H1 110(3) . . ?
C3 O3 H2 108(4) . . ?
C6 O4 H3 110(3) . . ?
C8 O5 H7 103(3) . . ?
C10 O7 H8 103(3) . . ?
C13 O8 H9 108(5) . . ?
O2 C1 O1 122.3(4) . . ?
O2 C1 C2 121.9(4) . . ?
O1 C1 C2 115.8(3) . . ?
C7 C2 C3 119.6(4) . . ?
C7 C2 C1 120.1(4) . . ?
C3 C2 C1 120.3(3) . . ?
O3 C3 C4 117.0(4) . . ?
O3 C3 C2 123.6(4) . . ?
C4 C3 C2 119.3(4) . . ?
C5 C4 C3 120.5(4) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.1(4) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 O4 118.7(4) . . ?
C7 C6 C5 120.0(3) . . ?
O4 C6 C5 121.2(4) . . ?
C6 C7 C2 120.4(4) . . ?
C6 C7 H6 119.8 . . ?
C2 C7 H6 119.8 . . ?
O6 C8 O5 122.0(4) . . ?
O6 C8 C9 122.9(4) . . ?
O5 C8 C9 115.2(3) . . ?
C14 C9 C10 119.4(4) . . ?
C14 C9 C8 120.4(4) . . ?
C10 C9 C8 120.2(3) . . ?
O7 C10 C11 117.2(4) . . ?
O7 C10 C9 123.4(4) . . ?
C11 C10 C9 119.4(4) . . ?
C12 C11 C10 120.0(4) . . ?
C12 C11 H10 120.0 . . ?
C10 C11 H10 120.0 . . ?
C13 C12 C11 120.8(4) . . ?
C13 C12 H11 119.6 . . ?
C11 C12 H11 119.6 . . ?
O8 C13 C14 121.3(5) . . ?
O8 C13 C12 118.8(4) . . ?
C14 C13 C12 120.0(3) . . ?
C13 C14 C9 120.4(4) . . ?
C13 C14 H12 119.8 . . ?
C9 C14 H12 119.8 . . ?

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
O2 C1 C2 C7 -179.0(4) . . . . ?
O1 C1 C2 C7 0.6(5) . . . . ?
O2 C1 C2 C3 1.5(6) . . . . ?
O1 C1 C2 C3 -178.9(4) . . . . ?
C7 C2 C3 O3 -178.8(4) . . . . ?
C1 C2 C3 O3 0.7(6) . . . . ?
C7 C2 C3 C4 0.5(6) . . . . ?
C1 C2 C3 C4 -180.0(4) . . . . ?
O3 C3 C4 C5 179.4(4) . . . . ?
C2 C3 C4 C5 0.1(6) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C4 C5 C6 C7 -1.3(6) . . . . ?
C4 C5 C6 O4 175.7(4) . . . . ?
O4 C6 C7 C2 -175.1(4) . . . . ?
C5 C6 C7 C2 2.0(6) . . . . ?
C3 C2 C7 C6 -1.6(6) . . . . ?
C1 C2 C7 C6 178.9(4) . . . . ?
O6 C8 C9 C14 179.0(4) . . . . ?
O5 C8 C9 C14 -1.3(5) . . . . ?
O6 C8 C9 C10 -0.6(6) . . . . ?
O5 C8 C9 C10 179.1(4) . . . . ?
C14 C9 C10 O7 -179.4(4) . . . . ?
C8 C9 C10 O7 0.1(6) . . . . ?
C14 C9 C10 C11 -0.3(6) . . . . ?
C8 C9 C10 C11 179.2(4) . . . . ?
O7 C10 C11 C12 179.5(4) . . . . ?
C9 C10 C11 C12 0.4(6) . . . . ?
C10 C11 C12 C13 -0.1(7) . . . . ?
C11 C12 C13 O8 -179.8(4) . . . . ?
C11 C12 C13 C14 -0.3(7) . . . . ?
O8 C13 C14 C9 179.9(4) . . . . ?
C12 C13 C14 C9 0.4(6) . . . . ?
C10 C9 C14 C13 -0.1(6) . . . . ?
C8 C9 C14 C13 -179.6(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 O6 . . . 2.678(4) 0.89(4) 1.79(4) 179(4) no
O3 H2 O2 . . . 2.628(4) 1.18(8) 1.75(9) 126(6) no
O4 H3 O8 . . 1_745 2.730(5) 0.93(5) 1.85(5) 158(5) no
O5 H7 O2 . . . 2.666(4) 1.13(6) 1.56(7) 163(6) no
O7 H8 O6 . . . 2.637(4) 0.97(5) 1.75(5) 150(4) no
O8 H9 O4 . . 1_465 2.768(5) 0.86(7) 1.92(7) 166(7) no

#==============================================================================
# start Validation Reply Form
_vrf_PLAT355_DHBA-Form-I         
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O3       - H2       .       1.18 Ang.  
RESPONSE: The refined positions of these hydrogen atoms have large 
ambiguity due to the artifacts of pseudo-inversion symmetry locating on 
the carboxylic acid dimer.
;
_vrf_PLAT111_DHBA-Form-I         
;
PROBLEM: ADDSYM Detects New (Pseudo) Centre of Symmetry .        100 %Fit  
RESPONSE: ...
;
_vrf_PLAT113_DHBA-Form-I         
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group      P21/c Check 
RESPONSE: The existence of pseudo-symmetry is essential observation for
 ferroelectric compounds.
;
# end Validation Reply Form

# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        '2,5-Dihydroxybenzoic acid'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
_exptl_crystal_preparation       ferroelectric
