# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_FDC-alpha
_database_code_depnum_ccdc_archive 'CCDC 2082229'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2021-05-07 deposited with the CCDC.	2021-10-06 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C6 H4 O5'
_chemical_formula_moiety         'C6 H4 O5'
_chemical_formula_weight         156.09
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
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,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   6.0486(3)
_cell_length_b                   14.4096(6)
_cell_length_c                   7.3391(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.538(4)
_cell_angle_gamma                90.0000
_cell_volume                     639.03(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3239
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      29.69
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320.00
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_T_max  0.978

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

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_reflns_number            5342
_diffrn_reflns_av_unetI/netI     0.0085
_diffrn_reflns_av_R_equivalents  0.0083
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.827
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1459
_reflns_number_gt                1186
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.0400
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.1228
_refine_ls_wR_factor_gt          0.1170
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         1459
_refine_ls_number_parameters     109
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0809P)²+0.0206P] 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         0.24
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.040(8)

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 0.33589(13) 0.04842(5) 0.18692(12) 0.0585(3) Uani 1 1 d . . . . .
O2 O 0.54344(11) 0.16481(5) 0.29166(10) 0.0486(3) Uani 1 1 d . . . . .
O3 O 0.54071(11) 0.34131(5) 0.28730(10) 0.0487(3) Uani 1 1 d . . . . .
O4 O 0.32201(13) 0.45096(5) 0.18050(13) 0.0596(3) Uani 1 1 d . . . . .
O5 O -0.12212(12) 0.24447(4) 0.01407(12) 0.0464(3) Uani 1 1 d . . . . .
C1 C 0.37420(14) 0.13632(6) 0.21294(13) 0.0378(3) Uani 1 1 d . . . . .
C2 C 0.35654(14) 0.36858(7) 0.20296(13) 0.0394(3) Uani 1 1 d . . . . .
C3 C 0.00281(15) 0.17030(7) 0.06449(13) 0.0428(3) Uani 1 1 d . . . . .
H3 H -0.040112 0.108747 0.048680 0.051 Uiso 1 1 calc R U . . .
C4 C 0.19972(14) 0.19830(6) 0.14146(11) 0.0353(3) Uani 1 1 d . . . . .
C5 C 0.19479(14) 0.29811(6) 0.13849(11) 0.0352(3) Uani 1 1 d . . . . .
C6 C -0.00447(15) 0.32135(7) 0.05946(13) 0.0417(3) Uani 1 1 d . . . . .
H4 H -0.053322 0.381835 0.039331 0.050 Uiso 1 1 calc R U . . .
H1 H 0.4677(19) 0.0108(8) 0.2395(12) 0.085(5) Uiso 1 1 d . . . . .
H2 H 0.549(3) 0.2675(8) 0.293(2) 0.078(5) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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 1.3002(12) . ?
O1 H1 1.025(13) . ?
O2 C1 1.2238(11) . ?
O3 C2 1.3104(11) . ?
O3 H2 1.065(12) . ?
O4 C2 1.2153(12) . ?
O5 C6 1.3504(11) . ?
O5 C3 1.3511(11) . ?
C1 C4 1.4621(12) . ?
C2 C5 1.4734(12) . ?
C3 C4 1.3568(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.4388(14) . ?
C5 C6 1.3562(12) . ?
C6 H4 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 109.2(6) . . ?
C2 O3 H2 110.8(9) . . ?
C6 O5 C3 107.41(9) . . ?
O2 C1 O1 122.41(8) . . ?
O2 C1 C4 122.67(9) . . ?
O1 C1 C4 114.91(8) . . ?
O4 C2 O3 119.62(8) . . ?
O4 C2 C5 121.46(8) . . ?
O3 C2 C5 118.92(8) . . ?
O5 C3 C4 110.42(8) . . ?
O5 C3 H3 124.8 . . ?
C4 C3 H3 124.8 . . ?
C3 C4 C5 105.89(7) . . ?
C3 C4 C1 125.04(8) . . ?
C5 C4 C1 129.07(7) . . ?
C6 C5 C4 105.71(7) . . ?
C6 C5 C2 122.15(8) . . ?
C4 C5 C2 132.14(7) . . ?
O5 C6 C5 110.59(8) . . ?
O5 C6 H4 124.7 . . ?
C5 C6 H4 124.7 . . ?

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
C6 O5 C3 C4 -0.14(13) . . . . ?
O5 C3 C4 C5 0.19(10) . . . . ?
O5 C3 C4 C1 179.43(8) . . . . ?
O2 C1 C4 C3 -175.23(9) . . . . ?
O1 C1 C4 C3 4.63(14) . . . . ?
O2 C1 C4 C5 3.82(14) . . . . ?
O1 C1 C4 C5 -176.32(8) . . . . ?
C3 C4 C5 C6 -0.18(8) . . . . ?
C1 C4 C5 C6 -179.37(9) . . . . ?
C3 C4 C5 C2 179.38(10) . . . . ?
C1 C4 C5 C2 0.19(12) . . . . ?
O4 C2 C5 C6 -3.37(15) . . . . ?
O3 C2 C5 C6 176.20(9) . . . . ?
O4 C2 C5 C4 177.14(9) . . . . ?
O3 C2 C5 C4 -3.30(14) . . . . ?
C3 O5 C6 C5 0.02(13) . . . . ?
C4 C5 C6 O5 0.10(10) . . . . ?
C2 C5 C6 O5 -179.51(8) . . . . ?

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 O4 . . 2_645 2.6500(11) 1.025(11) 1.625(11) 179.0(9) no
O3 H2 O2 . . . 2.5435(10) 1.065(12) 1.481(12) 175.3(15) no
O3 H2 O5 . . 4_666 2.8559(10) 1.065(12) 2.516(16) 97.4(9) no

# start Validation Reply Form
_vrf_PLAT110_FDC-alpha           
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check 
RESPONSE: ...
;
_vrf_PLAT112_FDC-alpha           
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem       c/2        100 %Fit  
RESPONSE: ...
;
_vrf_PLAT113_FDC-alpha           
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group      P21/m Check 
RESPONSE: These sets of pseudo-symmetries are intrinsic observation because 
          this crystal is potentially antiferroelectric.
;
# 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        'Furan-3,4-dicarboxylic acid'
_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_FDC-beta
_database_code_depnum_ccdc_archive 'CCDC 2082230'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2021-05-07 deposited with the CCDC.	2021-10-06 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C6 H4 O5'
_chemical_formula_moiety         'C6 H4 O5'
_chemical_formula_weight         156.09
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c m'
_space_group_name_Hall           '-P 2c 2b'
_space_group_IT_number           57
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,1/2+Z
3 +X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
5 -X,-Y,-Z
6 +X,+Y,-1/2-Z
7 -X,-1/2+Y,+Z
8 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   6.8922(4)
_cell_length_b                   14.3401(7)
_cell_length_c                   6.3738(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     629.95(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1650
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      29.86
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       trapezoid
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.230
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320.00
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.828
_exptl_absorpt_correction_T_max  0.966

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

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_reflns_number            2175
_diffrn_reflns_av_unetI/netI     0.0080
_diffrn_reflns_av_R_equivalents  0.0072
_diffrn_reflns_theta_max         27.466
_diffrn_reflns_theta_min         2.841
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       5
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             775
_reflns_number_gt                684
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.0398
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1090
_refine_ls_wR_factor_gt          0.1056
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         775
_refine_ls_number_parameters     73
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0869P)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          0.001
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 0.32956(15) 0.38323(7) 0.250000 0.0514(3) Uani 1 2 d S T P . .
O2 O 0.54201(14) 0.49857(7) 0.250000 0.0585(4) Uani 1 2 d S T P . .
O3 O 0.54592(14) 0.67610(7) 0.250000 0.0564(4) Uani 1 2 d S T P . .
O4 O 0.33327(14) 0.78843(6) 0.250000 0.0530(3) Uani 1 2 d S T P . .
O5 O -0.09640(15) 0.58446(5) 0.250000 0.0527(4) Uani 1 2 d S T P . .
C1 C 0.37465(18) 0.47149(9) 0.250000 0.0380(3) Uani 1 2 d S T P . .
C2 C 0.36557(17) 0.70508(9) 0.250000 0.0407(4) Uani 1 2 d S T P . .
C3 C 0.02008(18) 0.50870(9) 0.250000 0.0418(4) Uani 1 2 d S T P . .
H3 H -0.023034 0.447249 0.250000 0.050 Uiso 1 2 calc R U P . .
C4 C 0.20921(16) 0.53524(8) 0.250000 0.0342(3) Uani 1 2 d S T P . .
C5 C 0.20828(16) 0.63547(8) 0.250000 0.0374(3) Uani 1 2 d S T P . .
C6 C 0.01941(19) 0.66082(9) 0.250000 0.0486(4) Uani 1 2 d S T P . .
H4 H -0.024860 0.722086 0.250000 0.058 Uiso 1 2 calc R U P . .
H1 H 0.452(3) 0.3483(15) 0.250000 0.071(6) Uiso 1 2 d S . P . .
H2 H 0.550(4) 0.6048(19) 0.250000 0.080(8) Uiso 1 2 d S . P . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_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 1.3033(17) . ?
O1 H1 0.98(2) . ?
O2 C1 1.2170(16) . ?
O3 C2 1.3106(15) . ?
O3 H2 1.02(3) . ?
O4 C2 1.2158(17) . ?
O5 C3 1.3507(16) . ?
O5 C6 1.3551(15) . ?
C1 C4 1.4614(17) . ?
C2 C5 1.4737(17) . ?
C3 C4 1.3579(15) . ?
C3 H3 0.9300 . ?
C4 C5 1.4374(19) . ?
C5 C6 1.3515(15) . ?
C6 H4 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 106.9(11) . . ?
C2 O3 H2 109.9(15) . . ?
C3 O5 C6 107.45(13) . . ?
O2 C1 O1 122.40(12) . . ?
O2 C1 C4 122.67(12) . . ?
O1 C1 C4 114.92(11) . . ?
O4 C2 O3 119.04(11) . . ?
O4 C2 C5 122.09(11) . . ?
O3 C2 C5 118.87(11) . . ?
O5 C3 C4 110.19(12) . . ?
O5 C3 H3 124.9 . . ?
C4 C3 H3 124.9 . . ?
C3 C4 C5 106.02(9) . . ?
C3 C4 C1 125.01(11) . . ?
C5 C4 C1 128.97(9) . . ?
C6 C5 C4 105.86(9) . . ?
C6 C5 C2 121.76(11) . . ?
C4 C5 C2 132.38(9) . . ?
C5 C6 O5 110.48(12) . . ?
C5 C6 H4 124.8 . . ?
O5 C6 H4 124.8 . . ?

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
C6 O5 C3 C4 0.0 . . . . ?
O5 C3 C4 C5 0.0 . . . . ?
O5 C3 C4 C1 180.0 . . . . ?
O2 C1 C4 C3 180.0 . . . . ?
O1 C1 C4 C3 0.0 . . . . ?
O2 C1 C4 C5 0.0 . . . . ?
O1 C1 C4 C5 180.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C1 C4 C5 C6 180.0 . . . . ?
C3 C4 C5 C2 180.0 . . . . ?
C1 C4 C5 C2 0.0 . . . . ?
O4 C2 C5 C6 0.0 . . . . ?
O3 C2 C5 C6 180.0 . . . . ?
O4 C2 C5 C4 180.0 . . . . ?
O3 C2 C5 C4 0.0 . . . . ?
C4 C5 C6 O5 0.0 . . . . ?
C2 C5 C6 O5 180.0 . . . . ?
C3 O5 C6 C5 0.0 . . . . ?

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 O4 . . 4_645 2.6923(14) 0.98(2) 1.71(2) 179(2) no
O3 H2 O2 . . . 2.5459(14) 1.02(3) 1.52(3) 177(2) no
O3 H2 O5 . . 1_655 2.7936(14) 1.02(3) 2.46(3) 98.2(17) 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        'Furan-3,4-dicarboxylic acid'
_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_CPPLA
_database_code_depnum_ccdc_archive 'CCDC 2082232'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2021-05-07 deposited with the CCDC.	2021-10-06 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C9 H5 Cl O2'
_chemical_formula_moiety         'C9 H5 Cl O2'
_chemical_formula_weight         180.59
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.1124(2)
_cell_length_b                   7.3896(2)
_cell_length_c                   17.2936(5)
_cell_angle_alpha                79.979(2)
_cell_angle_beta                 79.262(2)
_cell_angle_gamma                65.828(3)
_cell_volume                     809.84(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5422
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      30.04
_cell_measurement_temperature    295
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368.00
_exptl_absorpt_coefficient_mu    0.419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.851
_exptl_absorpt_correction_T_max  0.939

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

_diffrn_ambient_temperature      295
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_reflns_number            12763
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_av_R_equivalents  0.0126
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.412
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3714
_reflns_number_gt                2405
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.0508
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.1189
_refine_ls_wR_factor_gt          0.1085
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3714
_refine_ls_number_parameters     225
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0532P)²+0.0911P] 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          0.001
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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)
;
Cl Cl 0.1484 0.1585
;
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
Cl1 Cl 0.22466(6) 1.11664(6) 0.93096(2) 0.06677(16) Uani 1 1 d . . . . .
Cl2 Cl 0.72352(7) 0.61436(6) 0.93267(2) 0.06718(16) Uani 1 1 d . . . . .
O1 O 0.2495(2) 0.56483(16) 0.49801(6) 0.0634(3) Uani 1 1 d . . . . .
O2 O 0.2447(2) 0.29580(14) 0.57194(6) 0.0672(3) Uani 1 1 d . . . . .
O3 O 0.7442(2) -0.18949(15) 0.56793(6) 0.0652(3) Uani 1 1 d . . . . .
O4 O 0.7471(2) 0.08643(15) 0.49565(5) 0.0669(3) Uani 1 1 d . . . . .
C1 C 0.2453(2) 0.46201(19) 0.56652(7) 0.0467(3) Uani 1 1 d . . . . .
C2 C 0.2401(2) 0.55362(19) 0.63412(8) 0.0478(3) Uani 1 1 d . . . . .
C3 C 0.2360(2) 0.64357(18) 0.68558(7) 0.0440(3) Uani 1 1 d . . . . .
C4 C 0.23177(19) 0.75712(18) 0.74546(7) 0.0390(3) Uani 1 1 d . . . . .
C5 C 0.2638(2) 0.93410(19) 0.72337(7) 0.0448(3) Uani 1 1 d . . . . .
H2 H 0.286152 0.977967 0.670026 0.054 Uiso 1 1 calc R U . . .
C6 C 0.2626(2) 1.04423(19) 0.78025(8) 0.0476(3) Uani 1 1 d . . . . .
H3 H 0.285092 1.161655 0.765670 0.057 Uiso 1 1 calc R U . . .
C7 C 0.2275(2) 0.97806(19) 0.85895(7) 0.0442(3) Uani 1 1 d . . . . .
C8 C 0.1933(2) 0.8043(2) 0.88227(7) 0.0474(3) Uani 1 1 d . . . . .
H4 H 0.168422 0.762825 0.935731 0.057 Uiso 1 1 calc R U . . .
C9 C 0.1967(2) 0.69321(19) 0.82535(7) 0.0440(3) Uani 1 1 d . . . . .
H5 H 0.175385 0.575243 0.840395 0.053 Uiso 1 1 calc R U . . .
C10 C 0.7447(2) -0.01252(18) 0.55943(8) 0.0469(3) Uani 1 1 d . . . . .
C11 C 0.7417(2) 0.06203(19) 0.63147(8) 0.0481(3) Uani 1 1 d . . . . .
C12 C 0.7375(2) 0.14952(19) 0.68400(7) 0.0446(3) Uani 1 1 d . . . . .
C13 C 0.73288(19) 0.26033(18) 0.74480(7) 0.0399(3) Uani 1 1 d . . . . .
C14 C 0.6978(2) 0.19436(19) 0.82430(7) 0.0451(3) Uani 1 1 d . . . . .
H7 H 0.676908 0.076066 0.838622 0.054 Uiso 1 1 calc R U . . .
C15 C 0.6938(2) 0.3036(2) 0.88212(7) 0.0486(3) Uani 1 1 d . . . . .
H8 H 0.669225 0.260277 0.935392 0.058 Uiso 1 1 calc R U . . .
C16 C 0.7268(2) 0.4780(2) 0.85988(7) 0.0446(3) Uani 1 1 d . . . . .
C17 C 0.7623(2) 0.5462(2) 0.78149(8) 0.0476(3) Uani 1 1 d . . . . .
H9 H 0.784443 0.663925 0.767603 0.057 Uiso 1 1 calc R U . . .
C18 C 0.7645(2) 0.43770(19) 0.72389(7) 0.0460(3) Uani 1 1 d . . . . .
H10 H 0.787146 0.482995 0.670739 0.055 Uiso 1 1 calc R U . . .
H1 H 0.252(3) 0.680(3) 0.5014(10) 0.113(7) Uiso 1 1 d . . . . .
H6 H 0.746(3) -0.226(2) 0.5182(12) 0.108(7) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_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
Cl1 C7 1.7371(13) . ?
Cl2 C16 1.7356(13) . ?
O1 C1 1.2938(16) . ?
O1 H1 0.87(2) . ?
O2 C1 1.2171(15) . ?
O3 C10 1.2917(15) . ?
O3 H6 0.94(2) . ?
O4 C10 1.2141(16) . ?
C1 C2 1.4372(17) . ?
C2 C3 1.1893(18) . ?
C3 C4 1.4309(16) . ?
C4 C9 1.3911(16) . ?
C4 C5 1.3951(17) . ?
C5 C6 1.3781(18) . ?
C5 H2 0.9300 . ?
C6 C7 1.3768(18) . ?
C6 H3 0.9300 . ?
C7 C8 1.3814(18) . ?
C8 C9 1.3787(17) . ?
C8 H4 0.9300 . ?
C9 H5 0.9300 . ?
C10 C11 1.4408(17) . ?
C11 C12 1.1927(18) . ?
C12 C13 1.4288(16) . ?
C13 C14 1.3887(16) . ?
C13 C18 1.3947(17) . ?
C14 C15 1.3799(17) . ?
C14 H7 0.9300 . ?
C15 C16 1.3802(19) . ?
C15 H8 0.9300 . ?
C16 C17 1.3764(18) . ?
C17 C18 1.3773(18) . ?
C17 H9 0.9300 . ?
C18 H10 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 112.0(12) . . ?
C10 O3 H6 109.7(10) . . ?
O2 C1 O1 120.27(13) . . ?
O2 C1 C2 122.69(12) . . ?
O1 C1 C2 117.04(11) . . ?
C3 C2 C1 174.26(13) . . ?
C2 C3 C4 178.03(13) . . ?
C9 C4 C5 119.57(11) . . ?
C9 C4 C3 120.92(11) . . ?
C5 C4 C3 119.51(11) . . ?
C6 C5 C4 120.30(11) . . ?
C6 C5 H2 119.8 . . ?
C4 C5 H2 119.8 . . ?
C7 C6 C5 119.10(12) . . ?
C7 C6 H3 120.5 . . ?
C5 C6 H3 120.5 . . ?
C6 C7 C8 121.67(12) . . ?
C6 C7 Cl1 119.34(10) . . ?
C8 C7 Cl1 118.99(10) . . ?
C9 C8 C7 119.20(12) . . ?
C9 C8 H4 120.4 . . ?
C7 C8 H4 120.4 . . ?
C8 C9 C4 120.16(11) . . ?
C8 C9 H5 119.9 . . ?
C4 C9 H5 119.9 . . ?
O4 C10 O3 123.16(12) . . ?
O4 C10 C11 121.46(11) . . ?
O3 C10 C11 115.38(11) . . ?
C12 C11 C10 170.14(13) . . ?
C11 C12 C13 177.87(13) . . ?
C14 C13 C18 119.45(11) . . ?
C14 C13 C12 121.17(11) . . ?
C18 C13 C12 119.39(11) . . ?
C15 C14 C13 120.28(12) . . ?
C15 C14 H7 119.9 . . ?
C13 C14 H7 119.9 . . ?
C14 C15 C16 119.14(12) . . ?
C14 C15 H8 120.4 . . ?
C16 C15 H8 120.4 . . ?
C17 C16 C15 121.65(12) . . ?
C17 C16 Cl2 119.25(10) . . ?
C15 C16 Cl2 119.10(10) . . ?
C16 C17 C18 119.08(12) . . ?
C16 C17 H9 120.5 . . ?
C18 C17 H9 120.5 . . ?
C17 C18 C13 120.40(11) . . ?
C17 C18 H10 119.8 . . ?
C13 C18 H10 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
C9 C4 C5 C6 0.6(2) . . . . ?
C3 C4 C5 C6 -179.29(12) . . . . ?
C4 C5 C6 C7 -0.6(2) . . . . ?
C5 C6 C7 C8 -0.1(2) . . . . ?
C5 C6 C7 Cl1 -179.76(10) . . . . ?
C6 C7 C8 C9 0.7(2) . . . . ?
Cl1 C7 C8 C9 -179.61(10) . . . . ?
C7 C8 C9 C4 -0.7(2) . . . . ?
C5 C4 C9 C8 0.1(2) . . . . ?
C3 C4 C9 C8 179.92(13) . . . . ?
C18 C13 C14 C15 0.1(2) . . . . ?
C12 C13 C14 C15 -179.98(13) . . . . ?
C13 C14 C15 C16 -0.5(2) . . . . ?
C14 C15 C16 C17 0.4(2) . . . . ?
C14 C15 C16 Cl2 -179.57(10) . . . . ?
C15 C16 C17 C18 0.1(2) . . . . ?
Cl2 C16 C17 C18 -179.91(11) . . . . ?
C16 C17 C18 C13 -0.5(2) . . . . ?
C14 C13 C18 C17 0.4(2) . . . . ?
C12 C13 C18 C17 -179.49(12) . . . . ?

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 O4 . . 2_666 2.6087(19) 0.87(3) 1.74(3) 177.6(18) no
O3 H6 O2 . . 2_656 2.6482(16) 0.94(2) 1.71(2) 178.6(14) no

# start Validation Reply Form
_vrf_PLAT110_CPPLA               
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check 
RESPONSE: ...
;
_vrf_PLAT112_CPPLA               
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem         C        100 %Fit  
RESPONSE: ...
;
_vrf_PLAT113_CPPLA               
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group        P-1 Check 
RESPONSE: These sets of pseudo-symmetries are intrinsic observation because 
          this crystal is antiferroelectric as evidenced by the 
          polarization measurements.         
;
# 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        '3-(4-chlorophenyl)propiolic acid'
_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_FDC-gamma
_database_code_depnum_ccdc_archive 'CCDC 2082231'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2021-05-07 deposited with the CCDC.	2021-10-06 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C6 H4 O5'
_chemical_formula_moiety         'C6 H4 O5'
_chemical_formula_weight         156.09
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.3918(2)
_cell_length_b                   12.7404(3)
_cell_length_c                   14.4174(4)
_cell_angle_alpha                86.877(2)
_cell_angle_beta                 75.177(2)
_cell_angle_gamma                77.696(2)
_cell_volume                     1282.42(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10348
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      29.71
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640.00
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.870
_exptl_absorpt_correction_T_max  0.978

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

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_reflns_number            18152
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.194
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5848
_reflns_number_gt                4737
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.0726
_refine_ls_R_factor_gt           0.0641
_refine_ls_wR_factor_ref         0.1619
_refine_ls_wR_factor_gt          0.1583
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         5848
_refine_ls_number_parameters     429
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0420P)²+1.4016P] 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          0.003
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.29
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 0.6882(3) -0.08506(15) 0.03985(13) 0.0508(5) Uani 1 1 d . . . . .
O2 O 0.6226(3) 0.02046(14) 0.16355(13) 0.0467(5) Uani 1 1 d . . . . .
O3 O 0.4733(3) 0.01383(14) 0.34282(12) 0.0441(5) Uani 1 1 d . . . . .
O4 O 0.3146(3) -0.09114(15) 0.44543(13) 0.0512(5) Uani 1 1 d . . . . .
O5 O 0.4697(3) -0.31390(14) 0.22780(13) 0.0451(5) Uani 1 1 d . . . . .
O6 O 0.1889(3) 0.08852(15) 0.54662(12) 0.0494(5) Uani 1 1 d . . . . .
O7 O 0.0410(3) -0.01945(14) 0.64720(13) 0.0450(5) Uani 1 1 d . . . . .
O8 O -0.1148(3) -0.02260(14) 0.82653(13) 0.0480(5) Uani 1 1 d . . . . .
O9 O -0.1814(3) 0.08188(16) 0.95364(13) 0.0495(5) Uani 1 1 d . . . . .
O10 O 0.0312(3) 0.30999(14) 0.76839(13) 0.0444(5) Uani 1 1 d . . . . .
O11 O 0.7374(3) 0.59358(15) 0.94689(13) 0.0502(5) Uani 1 1 d . . . . .
O12 O 0.6879(3) 0.48514(14) 0.84731(13) 0.0452(5) Uani 1 1 d . . . . .
O13 O 0.7124(3) 0.48032(14) 0.66838(13) 0.0477(5) Uani 1 1 d . . . . .
O14 O 0.7694(3) 0.58450(16) 0.54089(13) 0.0504(5) Uani 1 1 d . . . . .
O15 O 0.8030(3) 0.81338(13) 0.72403(13) 0.0439(5) Uani 1 1 d . . . . .
O16 O 0.7247(3) 0.41742(15) 0.45443(13) 0.0506(5) Uani 1 1 d . . . . .
O17 O 0.7869(3) 0.52323(15) 0.33133(14) 0.0480(5) Uani 1 1 d . . . . .
O18 O 0.8166(3) 0.51817(14) 0.15136(13) 0.0453(5) Uani 1 1 d . . . . .
O19 O 0.7633(4) 0.41339(16) 0.04765(13) 0.0510(6) Uani 1 1 d . . . . .
O20 O 0.6995(3) 0.18984(14) 0.26430(13) 0.0443(5) Uani 1 1 d . . . . .
C1 C 0.6226(4) -0.06986(19) 0.12636(16) 0.0336(5) Uani 1 1 d . . . . .
C2 C 0.4162(4) -0.07046(18) 0.36155(16) 0.0333(5) Uani 1 1 d . . . . .
C3 C 0.5485(4) -0.25185(19) 0.15535(18) 0.0398(6) Uani 1 1 d . . . . .
H3 H 0.597129 -0.273359 0.091623 0.048 Uiso 1 1 calc R U . . .
C4 C 0.5462(3) -0.15443(17) 0.18909(16) 0.0294(5) Uani 1 1 d . . . . .
C5 C 0.4575(3) -0.15621(17) 0.29043(16) 0.0296(5) Uani 1 1 d . . . . .
C6 C 0.4146(4) -0.25451(19) 0.30906(18) 0.0365(5) Uani 1 1 d . . . . .
H4 H 0.355590 -0.277961 0.369192 0.044 Uiso 1 1 calc R U . . .
C7 C 0.0969(4) 0.07139(18) 0.62722(16) 0.0341(5) Uani 1 1 d . . . . .
C8 C -0.1145(4) 0.06262(19) 0.86287(16) 0.0326(5) Uani 1 1 d . . . . .
C9 C 0.0874(4) 0.25165(19) 0.68662(18) 0.0373(5) Uani 1 1 d . . . . .
H7 H 0.144952 0.276409 0.626770 0.045 Uiso 1 1 calc R U . . .
C10 C 0.0484(3) 0.15242(17) 0.70375(16) 0.0290(5) Uani 1 1 d . . . . .
C11 C -0.0403(3) 0.14960(18) 0.80551(16) 0.0300(5) Uani 1 1 d . . . . .
C12 C -0.0458(4) 0.24722(19) 0.83973(18) 0.0393(6) Uani 1 1 d . . . . .
H8 H -0.095617 0.268272 0.903520 0.047 Uiso 1 1 calc R U . . .
C13 C 0.7255(4) 0.57589(18) 0.86662(17) 0.0343(5) Uani 1 1 d . . . . .
C14 C 0.7479(4) 0.56548(19) 0.63163(16) 0.0334(5) Uani 1 1 d . . . . .
C15 C 0.7777(4) 0.75558(19) 0.80631(17) 0.0351(5) Uani 1 1 d . . . . .
H11 H 0.776999 0.780457 0.865894 0.042 Uiso 1 1 calc R U . . .
C16 C 0.7537(3) 0.65650(17) 0.78965(15) 0.0293(5) Uani 1 1 d . . . . .
C17 C 0.7657(3) 0.65321(18) 0.68849(15) 0.0295(5) Uani 1 1 d . . . . .
C18 C 0.7953(4) 0.7503(2) 0.65323(18) 0.0392(6) Uani 1 1 d . . . . .
H12 H 0.808490 0.770891 0.589354 0.047 Uiso 1 1 calc R U . . .
C19 C 0.7482(4) 0.43301(19) 0.36790(17) 0.0344(5) Uani 1 1 d . . . . .
C20 C 0.7799(4) 0.43377(18) 0.13229(16) 0.0335(5) Uani 1 1 d . . . . .
C21 C 0.7044(4) 0.25164(19) 0.33707(18) 0.0392(6) Uani 1 1 d . . . . .
H15 H 0.688607 0.229644 0.400696 0.047 Uiso 1 1 calc R U . . .
C22 C 0.7352(3) 0.34919(17) 0.30468(16) 0.0300(5) Uani 1 1 d . . . . .
C23 C 0.7495(3) 0.34775(17) 0.20262(15) 0.0289(5) Uani 1 1 d . . . . .
C24 C 0.7265(4) 0.24966(19) 0.18333(18) 0.0371(5) Uani 1 1 d . . . . .
H16 H 0.728930 0.226417 0.122907 0.045 Uiso 1 1 calc R U . . .
H1 H 0.571(6) 0.027(3) 0.232(3) 0.096(14) Uiso 1 1 d . . . . .
H2 H 0.263(6) -0.025(4) 0.495(3) 0.123(18) Uiso 1 1 d . . . . .
H5 H -0.033(7) -0.023(4) 0.719(3) 0.112(16) Uiso 1 1 d . . . . .
H6 H -0.224(5) 0.025(3) 0.977(3) 0.078(12) Uiso 1 1 d . . . . .
H9 H 0.694(6) 0.477(3) 0.771(3) 0.102(14) Uiso 1 1 d . . . . .
H10 H 0.756(5) 0.529(3) 0.517(3) 0.077(12) Uiso 1 1 d . . . . .
H13 H 0.804(7) 0.519(4) 0.260(4) 0.113(16) Uiso 1 1 d . . . . .
H14 H 0.762(5) 0.472(3) 0.019(3) 0.069(11) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_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 1.227(3) . ?
O2 C1 1.295(3) . ?
O2 H1 0.97(4) . ?
O3 C2 1.228(3) . ?
O4 C2 1.296(3) . ?
O4 H2 1.07(5) . ?
O5 C6 1.354(3) . ?
O5 C3 1.360(3) . ?
O6 C7 1.221(3) . ?
O7 C7 1.304(3) . ?
O7 H5 1.04(5) . ?
O8 C8 1.231(3) . ?
O9 C8 1.292(3) . ?
O9 H6 0.87(4) . ?
O10 C12 1.351(3) . ?
O10 C9 1.352(3) . ?
O11 C13 1.219(3) . ?
O12 C13 1.305(3) . ?
O12 H9 1.10(5) . ?
O13 C14 1.231(3) . ?
O13 H9 1.45(5) . ?
O14 C14 1.293(3) . ?
O14 H10 0.84(4) . ?
O15 C18 1.352(3) . ?
O15 C15 1.354(3) . ?
O16 C19 1.226(3) . ?
O17 C19 1.295(3) . ?
O17 H13 1.00(5) . ?
O18 C20 1.225(3) . ?
O19 C20 1.302(3) . ?
O19 H14 0.84(4) . ?
O20 C24 1.354(3) . ?
O20 C21 1.358(3) . ?
C1 C4 1.480(3) . ?
C2 C5 1.469(3) . ?
C3 C4 1.353(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.441(3) . ?
C5 C6 1.353(3) . ?
C6 H4 0.9300 . ?
C7 C10 1.475(3) . ?
C8 C11 1.463(3) . ?
C9 C10 1.352(3) . ?
C9 H7 0.9300 . ?
C10 C11 1.448(3) . ?
C11 C12 1.352(3) . ?
C12 H8 0.9300 . ?
C13 C16 1.476(3) . ?
C14 C17 1.468(3) . ?
C15 C16 1.354(3) . ?
C15 H11 0.9300 . ?
C16 C17 1.441(3) . ?
C17 C18 1.352(3) . ?
C18 H12 0.9300 . ?
C19 C22 1.475(3) . ?
C20 C23 1.465(3) . ?
C21 C22 1.348(3) . ?
C21 H15 0.9300 . ?
C22 C23 1.449(3) . ?
C23 C24 1.349(3) . ?
C24 H16 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 O2 H1 116(3) . . ?
C2 O4 H2 115(2) . . ?
C6 O5 C3 107.27(18) . . ?
C7 O7 H5 112(3) . . ?
C8 O9 H6 105(2) . . ?
C12 O10 C9 107.34(19) . . ?
C13 O12 H9 113(2) . . ?
C14 O13 H9 112.9(17) . . ?
C14 O14 H10 106(3) . . ?
C18 O15 C15 107.39(18) . . ?
C19 O17 H13 107(3) . . ?
C20 O19 H14 104(2) . . ?
C24 O20 C21 107.14(18) . . ?
O1 C1 O2 119.8(2) . . ?
O1 C1 C4 120.6(2) . . ?
O2 C1 C4 119.5(2) . . ?
O3 C2 O4 122.9(2) . . ?
O3 C2 C5 122.6(2) . . ?
O4 C2 C5 114.5(2) . . ?
C4 C3 O5 110.4(2) . . ?
C4 C3 H3 124.8 . . ?
O5 C3 H3 124.8 . . ?
C3 C4 C5 105.8(2) . . ?
C3 C4 C1 122.5(2) . . ?
C5 C4 C1 131.7(2) . . ?
C6 C5 C4 106.1(2) . . ?
C6 C5 C2 125.2(2) . . ?
C4 C5 C2 128.6(2) . . ?
C5 C6 O5 110.4(2) . . ?
C5 C6 H4 124.8 . . ?
O5 C6 H4 124.8 . . ?
O6 C7 O7 120.4(2) . . ?
O6 C7 C10 120.8(2) . . ?
O7 C7 C10 118.8(2) . . ?
O8 C8 O9 122.5(2) . . ?
O8 C8 C11 122.0(2) . . ?
O9 C8 C11 115.5(2) . . ?
C10 C9 O10 110.7(2) . . ?
C10 C9 H7 124.6 . . ?
O10 C9 H7 124.6 . . ?
C9 C10 C11 105.5(2) . . ?
C9 C10 C7 122.2(2) . . ?
C11 C10 C7 132.3(2) . . ?
C12 C11 C10 105.8(2) . . ?
C12 C11 C8 125.1(2) . . ?
C10 C11 C8 129.1(2) . . ?
O10 C12 C11 110.6(2) . . ?
O10 C12 H8 124.7 . . ?
C11 C12 H8 124.7 . . ?
O11 C13 O12 120.5(2) . . ?
O11 C13 C16 120.6(2) . . ?
O12 C13 C16 118.9(2) . . ?
O13 C14 O14 122.5(2) . . ?
O13 C14 C17 122.1(2) . . ?
O14 C14 C17 115.5(2) . . ?
C16 C15 O15 110.5(2) . . ?
C16 C15 H11 124.8 . . ?
O15 C15 H11 124.8 . . ?
C15 C16 C17 105.67(19) . . ?
C15 C16 C13 122.1(2) . . ?
C17 C16 C13 132.2(2) . . ?
C18 C17 C16 106.1(2) . . ?
C18 C17 C14 124.9(2) . . ?
C16 C17 C14 129.0(2) . . ?
C17 C18 O15 110.4(2) . . ?
C17 C18 H12 124.8 . . ?
O15 C18 H12 124.8 . . ?
O16 C19 O17 119.9(2) . . ?
O16 C19 C22 120.5(2) . . ?
O17 C19 C22 119.6(2) . . ?
O18 C20 O19 122.6(2) . . ?
O18 C20 C23 123.0(2) . . ?
O19 C20 C23 114.4(2) . . ?
C22 C21 O20 110.9(2) . . ?
C22 C21 H15 124.6 . . ?
O20 C21 H15 124.6 . . ?
C21 C22 C23 105.4(2) . . ?
C21 C22 C19 122.8(2) . . ?
C23 C22 C19 131.8(2) . . ?
C24 C23 C22 106.1(2) . . ?
C24 C23 C20 125.4(2) . . ?
C22 C23 C20 128.5(2) . . ?
C23 C24 O20 110.5(2) . . ?
C23 C24 H16 124.8 . . ?
O20 C24 H16 124.8 . . ?

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
C6 O5 C3 C4 0.5(3) . . . . ?
O5 C3 C4 C5 -0.4(3) . . . . ?
O5 C3 C4 C1 -180.0(2) . . . . ?
O1 C1 C4 C3 1.5(4) . . . . ?
O2 C1 C4 C3 -177.5(3) . . . . ?
O1 C1 C4 C5 -177.8(3) . . . . ?
O2 C1 C4 C5 3.1(4) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C1 C4 C5 C6 179.6(3) . . . . ?
C3 C4 C5 C2 -178.9(3) . . . . ?
C1 C4 C5 C2 0.5(4) . . . . ?
O3 C2 C5 C6 173.3(3) . . . . ?
O4 C2 C5 C6 -6.8(4) . . . . ?
O3 C2 C5 C4 -7.8(4) . . . . ?
O4 C2 C5 C4 172.2(2) . . . . ?
C4 C5 C6 O5 0.1(3) . . . . ?
C2 C5 C6 O5 179.3(2) . . . . ?
C3 O5 C6 C5 -0.4(3) . . . . ?
C12 O10 C9 C10 -0.1(3) . . . . ?
O10 C9 C10 C11 0.1(3) . . . . ?
O10 C9 C10 C7 -179.3(2) . . . . ?
O6 C7 C10 C9 6.1(4) . . . . ?
O7 C7 C10 C9 -174.4(2) . . . . ?
O6 C7 C10 C11 -173.1(3) . . . . ?
O7 C7 C10 C11 6.4(4) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C7 C10 C11 C12 179.2(3) . . . . ?
C9 C10 C11 C8 178.8(3) . . . . ?
C7 C10 C11 C8 -1.9(4) . . . . ?
O8 C8 C11 C12 175.9(3) . . . . ?
O9 C8 C11 C12 -3.3(4) . . . . ?
O8 C8 C11 C10 -2.8(4) . . . . ?
O9 C8 C11 C10 178.0(2) . . . . ?
C9 O10 C12 C11 0.0(3) . . . . ?
C10 C11 C12 O10 0.1(3) . . . . ?
C8 C11 C12 O10 -178.9(2) . . . . ?
C18 O15 C15 C16 -0.1(3) . . . . ?
O15 C15 C16 C17 0.1(3) . . . . ?
O15 C15 C16 C13 179.3(2) . . . . ?
O11 C13 C16 C15 -5.6(4) . . . . ?
O12 C13 C16 C15 174.5(2) . . . . ?
O11 C13 C16 C17 173.3(3) . . . . ?
O12 C13 C16 C17 -6.6(4) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C13 C16 C17 C18 -179.2(3) . . . . ?
C15 C16 C17 C14 -179.4(2) . . . . ?
C13 C16 C17 C14 1.6(4) . . . . ?
O13 C14 C17 C18 -176.7(3) . . . . ?
O14 C14 C17 C18 2.4(4) . . . . ?
O13 C14 C17 C16 2.4(4) . . . . ?
O14 C14 C17 C16 -178.5(2) . . . . ?
C16 C17 C18 O15 0.1(3) . . . . ?
C14 C17 C18 O15 179.4(2) . . . . ?
C15 O15 C18 C17 0.0(3) . . . . ?
C24 O20 C21 C22 -0.4(3) . . . . ?
O20 C21 C22 C23 0.4(3) . . . . ?
O20 C21 C22 C19 -179.7(2) . . . . ?
O16 C19 C22 C21 -2.4(4) . . . . ?
O17 C19 C22 C21 176.8(3) . . . . ?
O16 C19 C22 C23 177.4(3) . . . . ?
O17 C19 C22 C23 -3.4(4) . . . . ?
C21 C22 C23 C24 -0.2(3) . . . . ?
C19 C22 C23 C24 180.0(3) . . . . ?
C21 C22 C23 C20 179.1(3) . . . . ?
C19 C22 C23 C20 -0.8(4) . . . . ?
O18 C20 C23 C24 -173.4(3) . . . . ?
O19 C20 C23 C24 7.0(4) . . . . ?
O18 C20 C23 C22 7.5(4) . . . . ?
O19 C20 C23 C22 -172.1(2) . . . . ?
C22 C23 C24 O20 -0.1(3) . . . . ?
C20 C23 C24 O20 -179.4(2) . . . . ?
C21 O20 C24 C23 0.3(3) . . . . ?

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
O2 H1 O3 . . . 2.542(2) 0.97(4) 1.58(4) 168(5) no
O2 H1 O20 . . . 2.894(3) 0.97(4) 2.57(5) 100(3) no
O4 H2 O6 . . . 2.645(3) 1.07(5) 1.59(5) 167(4) no
O7 H5 O8 . . . 2.549(2) 1.04(5) 1.51(5) 171(5) no
O9 H6 O1 . . 1_456 2.640(3) 0.87(4) 1.78(4) 173(4) no
O14 H10 O16 . . . 2.644(3) 0.84(4) 1.81(4) 174(4) no
O17 H13 O18 . . . 2.551(3) 1.00(5) 1.55(5) 176(4) no
O19 H14 O11 . . 1_554 2.647(3) 0.84(4) 1.81(4) 172(4) no

# start Validation Reply Form
_vrf_PLAT110_FDC-gamma           
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check 
RESPONSE: ...
;
_vrf_PLAT112_FDC-gamma           
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem       a/2        100 %Fit  
RESPONSE: ...
;
_vrf_PLAT113_FDC-gamma           
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group      P21/c Check 
RESPONSE: These sets of pseudo-symmetries are intrinsic observation because 
          this crystal is antiferroelectric as evidenced by the 
          polarization measurements.
;
_vrf_PLAT355_FDC-gamma           
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O4       - H2       .       1.08 Ang.  
RESPONSE: ...
;
_vrf_PLAT772_FDC-gamma           
;
PROBLEM: Suspect O-H Bond in CIF: O13      --H9        ..       1.45 Ang.  
RESPONSE: ...
;
_vrf_PLAT930_FDC-gamma           
;
PROBLEM: FCF-based   Twin Law ( 0 0 1)[-1 0 2] Est.d BASF       0.26 Check 
RESPONSE: ...
;
# 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        'Furan-3,4-dicarboxylic acid'
_exptl_crystal_recrystallization_method Sublimation
