# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2024

####################################################################### 
# 
# 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_RXNV2020-2
_database_code_depnum_ccdc_archive 'CCDC 2026990'
loop_
_audit_author_name
_audit_author_address
'Guillermo Zaragoza Verez'
;Universidade de Santiago de Compostela
Spain
;
_audit_update_record             
;
2020-09-02 deposited with the CCDC.	2024-04-16 downloaded from the CCDC.
;

_audit_creation_date             2020-07-29T10:03:37-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C12 H8 O4'
_chemical_formula_sum            'C12 H8 O4'
_chemical_formula_weight         216.18

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   10.9104(4)
_cell_length_b                   11.1907(4)
_cell_length_c                   15.6859(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1915.17(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8341
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      30.33
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.5
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS-2016/2'
_exptl_absorpt_correction_T_min  0.9002
_exptl_absorpt_correction_T_max  0.9604
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.991

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  'Incoatec multilayer mirror'
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III-14'
_diffrn_measurement_method       'omega and phi'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_number            26513
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.597
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_Friedel_coverage         0
_reflns_number_total             2382
_reflns_number_gt                2015
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'APPEX3v2018.7-2 (BRUKER AXS, 2005)'
_computing_cell_refinement       'APPEX3v2018.7-2 (BRUKER AXS, 2005)'
_computing_data_reduction        'APPEX3v2018.7-2 (BRUKER AXS, 2005)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0428P)²+0.8402P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2382
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0901
_refine_ls_wR_factor_gt          0.0851
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.046

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.65420(10) 0.37821(10) 0.38867(7) 0.0154(2) Uani 1 1 d . . . . .
H1 H 0.6656(13) 0.2966(13) 0.3668(9) 0.018 Uiso 1 1 d . U . . .
C2 C 0.68484(11) 0.40935(11) 0.46787(7) 0.0180(2) Uani 1 1 d . . . . .
H2 H 0.7190(13) 0.3521(14) 0.5089(9) 0.022 Uiso 1 1 d . U . . .
C3 C 0.67008(11) 0.53334(11) 0.49817(7) 0.0183(2) Uani 1 1 d . . . . .
C4 C 0.60272(11) 0.61561(11) 0.44162(8) 0.0176(2) Uani 1 1 d . . . . .
H4 H 0.5840(13) 0.6939(13) 0.4638(9) 0.021 Uiso 1 1 d . U . . .
C5 C 0.56821(11) 0.58272(11) 0.36352(7) 0.0162(2) Uani 1 1 d . . . . .
H5 H 0.5236(13) 0.6350(13) 0.3265(9) 0.019 Uiso 1 1 d . U . . .
C6 C 0.60527(10) 0.46576(10) 0.32538(7) 0.0138(2) Uani 1 1 d . . . . .
C7 C 0.69050(10) 0.47544(10) 0.24373(7) 0.0127(2) Uani 1 1 d . . . . .
H7 H 0.7688(13) 0.4334(12) 0.2492(9) 0.015 Uiso 1 1 d . U . . .
C8 C 0.58703(10) 0.41054(10) 0.19717(7) 0.0138(2) Uani 1 1 d . . . . .
H8 H 0.6062(12) 0.3284(13) 0.1799(9) 0.017 Uiso 1 1 d . U . . .
C9 C 0.52191(10) 0.47579(11) 0.12618(7) 0.0164(2) Uani 1 1 d . . . . .
C10 C 0.54066(11) 0.60572(11) 0.11866(8) 0.0187(3) Uani 1 1 d . . . . .
H10 H 0.4874(14) 0.6468(13) 0.0799(9) 0.022 Uiso 1 1 d . U . . .
C11 C 0.63027(12) 0.66326(11) 0.15939(7) 0.0184(2) Uani 1 1 d . . . . .
H11 H 0.6446(14) 0.7469(14) 0.1514(9) 0.022 Uiso 1 1 d . U . . .
C12 C 0.71670(10) 0.60235(10) 0.21748(7) 0.0153(2) Uani 1 1 d . . . . .
O1 O 0.70971(9) 0.56603(9) 0.56763(6) 0.0274(2) Uani 1 1 d . . . . .
O2 O 0.50841(7) 0.41268(7) 0.27286(5) 0.01674(19) Uani 1 1 d . . . . .
O3 O 0.80541(8) 0.65490(8) 0.24678(6) 0.0228(2) Uani 1 1 d . . . . .
O4 O 0.45288(9) 0.42158(9) 0.07894(6) 0.0269(2) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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
C1 C2 1.3329(16) . ?
C1 C6 1.4935(16) . ?
C1 H1 0.983(14) . ?
C2 C3 1.4755(17) . ?
C2 H2 0.982(15) . ?
C3 O1 1.2279(15) . ?
C3 C4 1.4746(17) . ?
C4 C5 1.3335(17) . ?
C4 H4 0.964(15) . ?
C5 C6 1.4948(16) . ?
C5 H5 0.957(15) . ?
C6 O2 1.4657(13) . ?
C6 C7 1.5864(15) . ?
C7 C12 1.5061(15) . ?
C7 C8 1.5282(15) . ?
C7 H7 0.979(14) . ?
C8 O2 1.4650(13) . ?
C8 C9 1.5092(16) . ?
C8 H8 0.981(14) . ?
C9 O4 1.2183(14) . ?
C9 C10 1.4731(17) . ?
C10 C11 1.3337(18) . ?
C10 H10 0.959(15) . ?
C11 C12 1.4779(17) . ?
C11 H11 0.957(16) . ?
C12 O3 1.2222(14) . ?

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 C1 C6 122.53(11) . . ?
C2 C1 H1 122.5(8) . . ?
C6 C1 H1 115.0(8) . . ?
C1 C2 C3 121.24(11) . . ?
C1 C2 H2 122.4(9) . . ?
C3 C2 H2 116.4(9) . . ?
O1 C3 C4 121.55(11) . . ?
O1 C3 C2 121.83(11) . . ?
C4 C3 C2 116.60(10) . . ?
C5 C4 C3 121.40(11) . . ?
C5 C4 H4 121.5(9) . . ?
C3 C4 H4 117.1(9) . . ?
C4 C5 C6 122.21(11) . . ?
C4 C5 H5 122.2(9) . . ?
C6 C5 H5 115.5(9) . . ?
O2 C6 C1 111.44(9) . . ?
O2 C6 C5 112.63(9) . . ?
C1 C6 C5 113.90(9) . . ?
O2 C6 C7 89.80(8) . . ?
C1 C6 C7 111.83(9) . . ?
C5 C6 C7 114.95(9) . . ?
C12 C7 C8 117.24(9) . . ?
C12 C7 C6 113.35(9) . . ?
C8 C7 C6 85.43(8) . . ?
C12 C7 H7 108.1(8) . . ?
C8 C7 H7 117.3(8) . . ?
C6 C7 H7 114.1(8) . . ?
O2 C8 C9 108.33(9) . . ?
O2 C8 C7 92.14(8) . . ?
C9 C8 C7 118.07(9) . . ?
O2 C8 H8 111.3(8) . . ?
C9 C8 H8 110.5(8) . . ?
C7 C8 H8 114.8(8) . . ?
O4 C9 C10 121.91(11) . . ?
O4 C9 C8 119.93(11) . . ?
C10 C9 C8 118.12(10) . . ?
C11 C10 C9 122.68(11) . . ?
C11 C10 H10 121.1(9) . . ?
C9 C10 H10 116.1(9) . . ?
C10 C11 C12 122.72(11) . . ?
C10 C11 H11 122.0(9) . . ?
C12 C11 H11 115.3(9) . . ?
O3 C12 C11 121.01(11) . . ?
O3 C12 C7 120.08(11) . . ?
C11 C12 C7 118.84(10) . . ?
C8 O2 C6 92.29(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 C1 C2 C3 0.98(18) . . . . ?
C1 C2 C3 O1 -172.18(12) . . . . ?
C1 C2 C3 C4 9.17(17) . . . . ?
O1 C3 C4 C5 174.66(12) . . . . ?
C2 C3 C4 C5 -6.69(17) . . . . ?
C3 C4 C5 C6 -5.85(18) . . . . ?
C2 C1 C6 O2 -141.49(11) . . . . ?
C2 C1 C6 C5 -12.74(16) . . . . ?
C2 C1 C6 C7 119.69(12) . . . . ?
C4 C5 C6 O2 143.37(11) . . . . ?
C4 C5 C6 C1 15.22(16) . . . . ?
C4 C5 C6 C7 -115.68(12) . . . . ?
O2 C6 C7 C12 113.54(10) . . . . ?
C1 C6 C7 C12 -133.36(10) . . . . ?
C5 C6 C7 C12 -1.46(13) . . . . ?
O2 C6 C7 C8 -4.21(8) . . . . ?
C1 C6 C7 C8 108.89(10) . . . . ?
C5 C6 C7 C8 -119.21(10) . . . . ?
C12 C7 C8 O2 -109.75(10) . . . . ?
C6 C7 C8 O2 4.21(8) . . . . ?
C12 C7 C8 C9 2.37(14) . . . . ?
C6 C7 C8 C9 116.33(10) . . . . ?
O2 C8 C9 O4 -88.77(13) . . . . ?
C7 C8 C9 O4 168.45(10) . . . . ?
O2 C8 C9 C10 88.77(12) . . . . ?
C7 C8 C9 C10 -14.02(15) . . . . ?
O4 C9 C10 C11 -168.25(12) . . . . ?
C8 C9 C10 C11 14.27(17) . . . . ?
C9 C10 C11 C12 -1.66(18) . . . . ?
C10 C11 C12 O3 172.24(11) . . . . ?
C10 C11 C12 C7 -10.73(17) . . . . ?
C8 C7 C12 O3 -173.21(10) . . . . ?
C6 C7 C12 O3 89.62(12) . . . . ?
C8 C7 C12 C11 9.73(14) . . . . ?
C6 C7 C12 C11 -87.44(12) . . . . ?
C9 C8 O2 C6 -125.10(9) . . . . ?
C7 C8 O2 C6 -4.55(8) . . . . ?
C1 C6 O2 C8 -109.08(9) . . . . ?
C5 C6 O2 C8 121.48(9) . . . . ?
C7 C6 O2 C8 4.38(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 O3 0.983(14) 2.482(14) 3.3753(14) 151.0(11) 6_755 yes
C8 H8 O3 0.981(14) 2.408(14) 3.1886(14) 136.1(11) 6_755 yes
C11 H11 O1 0.957(16) 2.572(15) 3.4642(15) 155.2(12) 7_575 yes



# END of CIF
####################################################################### 
# 
# 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_RXNV2020-3
_database_code_depnum_ccdc_archive 'CCDC 2026991'
loop_
_audit_author_name
_audit_author_address
'Guillermo Zaragoza Verez'
;Universidade de Santiago de Compostela
Spain
;
_audit_update_record             
;
2020-09-02 deposited with the CCDC.	2024-04-16 downloaded from the CCDC.
;

_audit_creation_date             2020-07-29T08:53:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C20 H12 O4'
_chemical_formula_sum            'C20 H12 O4'
_chemical_formula_weight         316.3

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1365(5)
_cell_length_b                   20.6845(12)
_cell_length_c                   8.5612(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.619(2)
_cell_angle_gamma                90
_cell_volume                     1428.12(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9791
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      28.31
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#


_exptl_crystal_description       plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS-2016/2'
_exptl_absorpt_correction_T_min  0.9362
_exptl_absorpt_correction_T_max  0.9593
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.995

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  'Incoatec multilayer mirror'
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III-14'
_diffrn_measurement_method       'omega and phi'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_number            71755
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.969
_diffrn_reflns_theta_max         28.276
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             3544
_reflns_number_gt                3039
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#


_computing_data_collection       'APPEX3v2018.7-2 (BRUKER AXS, 2005)'
_computing_cell_refinement       'APPEX3v2018.7-2 (BRUKER AXS, 2005)'
_computing_data_reduction        'APPEX3v2018.7-2 (BRUKER AXS, 2005)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0436P)²+0.5980P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3544
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0933
_refine_ls_wR_factor_gt          0.0887
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.044

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.07372(13) 0.43588(5) 0.27899(12) 0.0136(2) Uani 1 1 d . . . . .
C2 C 0.10185(13) 0.49453(5) 0.20584(12) 0.0145(2) Uani 1 1 d . . . . .
C3 C 0.25810(14) 0.50592(5) 0.13767(12) 0.0167(2) Uani 1 1 d . . . . .
C4 C 0.37226(14) 0.45074(6) 0.13608(13) 0.0186(2) Uani 1 1 d . . . . .
H4 H 0.4677(19) 0.4575(7) 0.0800(17) 0.022 Uiso 1 1 d . U . . .
C5 C 0.34478(14) 0.39512(6) 0.20511(13) 0.0171(2) Uani 1 1 d . . . . .
H5 H 0.4210(18) 0.3593(7) 0.2027(17) 0.02 Uiso 1 1 d . U . . .
C6 C 0.20295(13) 0.38356(5) 0.29552(12) 0.0132(2) Uani 1 1 d . . . . .
C7 C 0.25809(13) 0.35889(5) 0.46855(12) 0.0128(2) Uani 1 1 d . . . . .
H7 H 0.1882(17) 0.3780(7) 0.5409(16) 0.015 Uiso 1 1 d . U . . .
C8 C 0.19871(13) 0.29263(5) 0.40739(13) 0.0143(2) Uani 1 1 d . . . . .
H8 H 0.1112(18) 0.2720(7) 0.4608(17) 0.017 Uiso 1 1 d . U . . .
C9 C 0.32928(14) 0.24216(5) 0.38690(13) 0.0152(2) Uani 1 1 d . . . . .
C10 C 0.49864(13) 0.25167(5) 0.47253(12) 0.0144(2) Uani 1 1 d . . . . .
C11 C 0.54983(13) 0.31145(5) 0.54090(12) 0.0141(2) Uani 1 1 d . . . . .
C12 C 0.43762(13) 0.36860(5) 0.53338(12) 0.0138(2) Uani 1 1 d . . . . .
C13 C -0.02128(15) 0.54238(6) 0.19042(13) 0.0182(2) Uani 1 1 d . . . . .
H13 H -0.0008(18) 0.5821(7) 0.1372(18) 0.022 Uiso 1 1 d . U . . .
C14 C -0.16993(15) 0.53174(6) 0.24761(13) 0.0196(2) Uani 1 1 d . . . . .
H14 H -0.2556(19) 0.5633(7) 0.2340(18) 0.024 Uiso 1 1 d . U . . .
C15 C -0.19626(14) 0.47415(6) 0.32515(13) 0.0194(2) Uani 1 1 d . . . . .
H15 H -0.3004(19) 0.4666(7) 0.3651(18) 0.023 Uiso 1 1 d . U . . .
C16 C -0.07574(14) 0.42650(6) 0.33980(13) 0.0172(2) Uani 1 1 d . . . . .
H16 H -0.0948(18) 0.3869(7) 0.3899(17) 0.021 Uiso 1 1 d . U . . .
C17 C 0.71154(14) 0.31853(6) 0.61765(13) 0.0175(2) Uani 1 1 d . . . . .
H17 H 0.7436(18) 0.3608(7) 0.6654(17) 0.021 Uiso 1 1 d . U . . .
C18 C 0.81934(15) 0.26630(6) 0.62843(14) 0.0203(2) Uani 1 1 d . . . . .
H18 H 0.9322(19) 0.2717(7) 0.6827(18) 0.024 Uiso 1 1 d . U . . .
C19 C 0.76865(15) 0.20709(6) 0.56126(14) 0.0202(2) Uani 1 1 d . . . . .
H19 H 0.8423(19) 0.1706(7) 0.5703(18) 0.024 Uiso 1 1 d . U . . .
C20 C 0.60973(15) 0.19979(6) 0.48241(13) 0.0180(2) Uani 1 1 d . . . . .
H20 H 0.5732(18) 0.1589(7) 0.4357(17) 0.022 Uiso 1 1 d . U . . .
O1 O 0.28873(11) 0.55815(4) 0.08115(10) 0.0239(2) Uani 1 1 d . . . . .
O2 O 0.13010(10) 0.31930(4) 0.25492(9) 0.01752(18) Uani 1 1 d . . . . .
O3 O 0.48818(10) 0.42190(4) 0.57567(10) 0.01982(18) Uani 1 1 d . . . . .
O4 O 0.29178(11) 0.19583(4) 0.30182(11) 0.0234(2) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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
C1 C2 1.3979(15) . ?
C1 C16 1.3983(15) . ?
C1 C6 1.5025(14) . ?
C2 C13 1.4021(16) . ?
C2 C3 1.4863(15) . ?
C3 O1 1.2228(14) . ?
C3 C4 1.4728(16) . ?
C4 C5 1.3259(17) . ?
C4 H4 0.975(15) . ?
C5 C6 1.4916(15) . ?
C5 H5 0.968(15) . ?
C6 O2 1.4779(13) . ?
C6 C7 1.5747(14) . ?
C7 C12 1.5057(15) . ?
C7 C8 1.5228(15) . ?
C7 H7 0.978(14) . ?
C8 O2 1.4582(13) . ?
C8 C9 1.5161(15) . ?
C8 H8 0.992(14) . ?
C9 O4 1.2178(14) . ?
C9 C10 1.4857(15) . ?
C10 C20 1.3983(15) . ?
C10 C11 1.4072(15) . ?
C11 C17 1.3982(15) . ?
C11 C12 1.4898(14) . ?
C12 O3 1.2151(13) . ?
C13 C14 1.3814(17) . ?
C13 H13 0.964(15) . ?
C14 C15 1.3940(18) . ?
C14 H14 0.950(15) . ?
C15 C16 1.3842(16) . ?
C15 H15 0.967(15) . ?
C16 H16 0.947(15) . ?
C17 C18 1.3868(16) . ?
C17 H17 0.986(15) . ?
C18 C19 1.3921(18) . ?
C18 H18 0.979(15) . ?
C19 C20 1.3853(17) . ?
C19 H19 0.960(16) . ?
C20 H20 0.966(15) . ?

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 C1 C16 119.29(10) . . ?
C2 C1 C6 120.88(10) . . ?
C16 C1 C6 119.82(10) . . ?
C1 C2 C13 119.83(10) . . ?
C1 C2 C3 120.86(10) . . ?
C13 C2 C3 119.26(10) . . ?
O1 C3 C4 121.27(11) . . ?
O1 C3 C2 121.69(11) . . ?
C4 C3 C2 117.00(10) . . ?
C5 C4 C3 121.64(10) . . ?
C5 C4 H4 122.4(9) . . ?
C3 C4 H4 116.0(9) . . ?
C4 C5 C6 123.93(10) . . ?
C4 C5 H5 120.5(9) . . ?
C6 C5 H5 115.5(9) . . ?
O2 C6 C5 109.63(9) . . ?
O2 C6 C1 111.83(8) . . ?
C5 C6 C1 114.55(9) . . ?
O2 C6 C7 89.15(7) . . ?
C5 C6 C7 113.37(9) . . ?
C1 C6 C7 115.50(9) . . ?
C12 C7 C8 119.66(9) . . ?
C12 C7 C6 116.43(9) . . ?
C8 C7 C6 86.00(8) . . ?
C12 C7 H7 109.2(8) . . ?
C8 C7 H7 113.4(8) . . ?
C6 C7 H7 110.3(8) . . ?
O2 C8 C9 110.36(9) . . ?
O2 C8 C7 91.93(8) . . ?
C9 C8 C7 117.66(9) . . ?
O2 C8 H8 111.2(8) . . ?
C9 C8 H8 108.3(8) . . ?
C7 C8 H8 116.3(8) . . ?
O4 C9 C10 122.80(10) . . ?
O4 C9 C8 119.16(10) . . ?
C10 C9 C8 118.04(9) . . ?
C20 C10 C11 119.72(10) . . ?
C20 C10 C9 118.56(10) . . ?
C11 C10 C9 121.71(10) . . ?
C17 C11 C10 119.71(10) . . ?
C17 C11 C12 118.06(10) . . ?
C10 C11 C12 122.23(10) . . ?
O3 C12 C11 121.72(10) . . ?
O3 C12 C7 120.29(10) . . ?
C11 C12 C7 117.98(9) . . ?
C14 C13 C2 120.16(11) . . ?
C14 C13 H13 121.2(9) . . ?
C2 C13 H13 118.7(9) . . ?
C13 C14 C15 120.14(11) . . ?
C13 C14 H14 120.6(9) . . ?
C15 C14 H14 119.2(9) . . ?
C16 C15 C14 119.98(11) . . ?
C16 C15 H15 119.7(9) . . ?
C14 C15 H15 120.2(9) . . ?
C15 C16 C1 120.54(11) . . ?
C15 C16 H16 120.0(9) . . ?
C1 C16 H16 119.5(9) . . ?
C18 C17 C11 119.81(11) . . ?
C18 C17 H17 122.2(9) . . ?
C11 C17 H17 118.0(8) . . ?
C17 C18 C19 120.51(11) . . ?
C17 C18 H18 119.3(9) . . ?
C19 C18 H18 120.2(9) . . ?
C20 C19 C18 120.23(11) . . ?
C20 C19 H19 119.1(9) . . ?
C18 C19 H19 120.7(9) . . ?
C19 C20 C10 120.00(11) . . ?
C19 C20 H20 120.9(9) . . ?
C10 C20 H20 119.1(9) . . ?
C8 O2 C6 92.05(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
C16 C1 C2 C13 -1.74(16) . . . . ?
C6 C1 C2 C13 179.37(10) . . . . ?
C16 C1 C2 C3 -179.08(10) . . . . ?
C6 C1 C2 C3 2.03(15) . . . . ?
C1 C2 C3 O1 -175.85(10) . . . . ?
C13 C2 C3 O1 6.80(16) . . . . ?
C1 C2 C3 C4 6.23(15) . . . . ?
C13 C2 C3 C4 -171.13(10) . . . . ?
O1 C3 C4 C5 176.03(11) . . . . ?
C2 C3 C4 C5 -6.03(16) . . . . ?
C3 C4 C5 C6 -2.70(18) . . . . ?
C4 C5 C6 O2 137.28(11) . . . . ?
C4 C5 C6 C1 10.62(16) . . . . ?
C4 C5 C6 C7 -124.85(12) . . . . ?
C2 C1 C6 O2 -135.54(10) . . . . ?
C16 C1 C6 O2 45.59(13) . . . . ?
C2 C1 C6 C5 -10.02(14) . . . . ?
C16 C1 C6 C5 171.10(10) . . . . ?
C2 C1 C6 C7 124.48(11) . . . . ?
C16 C1 C6 C7 -54.40(13) . . . . ?
O2 C6 C7 C12 128.10(9) . . . . ?
C5 C6 C7 C12 17.02(13) . . . . ?
C1 C6 C7 C12 -118.02(10) . . . . ?
O2 C6 C7 C8 6.82(7) . . . . ?
C5 C6 C7 C8 -104.26(10) . . . . ?
C1 C6 C7 C8 120.71(9) . . . . ?
C12 C7 C8 O2 -125.18(9) . . . . ?
C6 C7 C8 O2 -6.92(7) . . . . ?
C12 C7 C8 C9 -10.94(14) . . . . ?
C6 C7 C8 C9 107.33(10) . . . . ?
O2 C8 C9 O4 -57.24(13) . . . . ?
C7 C8 C9 O4 -160.84(10) . . . . ?
O2 C8 C9 C10 122.78(10) . . . . ?
C7 C8 C9 C10 19.19(14) . . . . ?
O4 C9 C10 C20 -13.44(16) . . . . ?
C8 C9 C10 C20 166.53(10) . . . . ?
O4 C9 C10 C11 165.51(11) . . . . ?
C8 C9 C10 C11 -14.52(15) . . . . ?
C20 C10 C11 C17 0.23(16) . . . . ?
C9 C10 C11 C17 -178.71(10) . . . . ?
C20 C10 C11 C12 179.59(10) . . . . ?
C9 C10 C11 C12 0.65(16) . . . . ?
C17 C11 C12 O3 8.40(16) . . . . ?
C10 C11 C12 O3 -170.98(10) . . . . ?
C17 C11 C12 C7 -172.68(9) . . . . ?
C10 C11 C12 C7 7.95(15) . . . . ?
C8 C7 C12 O3 176.53(10) . . . . ?
C6 C7 C12 O3 75.38(13) . . . . ?
C8 C7 C12 C11 -2.41(14) . . . . ?
C6 C7 C12 C11 -103.56(11) . . . . ?
C1 C2 C13 C14 0.13(16) . . . . ?
C3 C2 C13 C14 177.51(10) . . . . ?
C2 C13 C14 C15 1.95(17) . . . . ?
C13 C14 C15 C16 -2.41(17) . . . . ?
C14 C15 C16 C1 0.77(17) . . . . ?
C2 C1 C16 C15 1.29(16) . . . . ?
C6 C1 C16 C15 -179.81(10) . . . . ?
C10 C11 C17 C18 -1.20(16) . . . . ?
C12 C11 C17 C18 179.41(10) . . . . ?
C11 C17 C18 C19 1.01(17) . . . . ?
C17 C18 C19 C20 0.18(18) . . . . ?
C18 C19 C20 C10 -1.16(17) . . . . ?
C11 C10 C20 C19 0.95(16) . . . . ?
C9 C10 C20 C19 179.92(10) . . . . ?
C9 C8 O2 C6 -113.17(9) . . . . ?
C7 C8 O2 C6 7.36(8) . . . . ?
C5 C6 O2 C8 107.46(9) . . . . ?
C1 C6 O2 C8 -124.36(9) . . . . ?
C7 C6 O2 C8 -7.11(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4 H4 O1 0.975(15) 2.581(15) 3.5301(15) 164.3(12) 3_665 yes



# END of CIF
