# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_cu_zhiwang01_0m
_database_code_depnum_ccdc_archive 'CCDC 2021369'
loop_
_audit_author_name
_audit_author_address
'Angel Ugrinov'
;North Dakota State University
United States of America
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2020-10-26 downloaded from the CCDC.
;
_audit_creation_date             2020-06-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H8 O4'
_chemical_formula_sum            'C9 H8 O4'
_chemical_formula_weight         180.15
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.6967(2)
_cell_length_b                   5.7405(2)
_cell_length_c                   20.7844(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.953(3)
_cell_angle_gamma                90
_cell_volume                     796.02(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2632
_cell_measurement_temperature    107.0
_cell_measurement_theta_max      66.582
_cell_measurement_theta_min      4.270
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    1.020
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0576 before and 0.0460 after correction.
The Ratio of minimum to maximum transmission is 0.8997.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       chunk
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.057
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8004
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.652
_diffrn_reflns_theta_max         66.652
_diffrn_reflns_theta_min         4.270
_diffrn_ambient_temperature      107.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           0.64
_diffrn_source_power             0.0286848
_diffrn_source_voltage           44.82
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1212
_reflns_number_total             1408
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1408
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0496P)²+0.3108P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0906
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00A(H00A), C00B(H00B), C00D(H00D)
2.b Idealised tetrahedral OH refined as rotating group:
 O001(H001), O002(H002), O004(H004)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.78855(15) 0.30740(18) 0.51322(5) 0.0192(3) Uani 1 1 d . . . . .
H1 H 0.889008 0.323734 0.492073 0.029 Uiso 1 1 calc R U . . .
O4 O -0.19782(15) 0.27177(18) 0.73734(5) 0.0204(3) Uani 1 1 d . . . . .
H7 H -0.212676 0.391190 0.759793 0.031 Uiso 1 1 calc R U . . .
O2 O 0.89269(15) 0.65397(18) 0.55200(5) 0.0207(3) Uani 1 1 d . . . . .
O3 O -0.14970(15) -0.04241(18) 0.65039(5) 0.0207(3) Uani 1 1 d . . . . .
H6 H -0.124839 -0.132569 0.620270 0.031 Uiso 1 1 calc R U . . .
C6 C -0.0085(2) 0.1285(3) 0.65653(6) 0.0163(3) Uani 1 1 d . . . . .
C4 C 0.2946(2) 0.3214(3) 0.62912(6) 0.0165(3) Uani 1 1 d . . . . .
C7 C -0.0371(2) 0.3012(3) 0.70225(7) 0.0158(3) Uani 1 1 d . . . . .
C9 C 0.2620(2) 0.4946(3) 0.67435(7) 0.0180(3) Uani 1 1 d . . . . .
H9 H 0.353111 0.621144 0.680142 0.022 Uiso 1 1 calc R U . . .
C3 C 0.4668(2) 0.3231(3) 0.59059(6) 0.0172(3) Uani 1 1 d . . . . .
H3 H 0.482579 0.193203 0.563168 0.021 Uiso 1 1 calc R U . . .
C5 C 0.1570(2) 0.1381(3) 0.62087(7) 0.0165(3) Uani 1 1 d . . . . .
H5 H 0.177180 0.018673 0.590451 0.020 Uiso 1 1 calc R U . . .
C8 C 0.0984(2) 0.4841(3) 0.71087(7) 0.0178(3) Uani 1 1 d . . . . .
H8 H 0.078924 0.602090 0.741769 0.021 Uiso 1 1 calc R U . . .
C1 C 0.7721(2) 0.4893(3) 0.55066(7) 0.0171(3) Uani 1 1 d . . . . .
C2 C 0.6038(2) 0.4918(3) 0.59064(7) 0.0188(3) Uani 1 1 d . . . . .
H2 H 0.590876 0.621367 0.618416 0.023 Uiso 1 1 calc R U . . .


_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 H1 0.8400 . ?
O1 C1 1.3126(18) . ?
O4 H7 0.8400 . ?
O4 C7 1.3620(17) . ?
O2 C1 1.2419(18) . ?
O3 H6 0.8400 . ?
O3 C6 1.3610(17) . ?
C6 C7 1.397(2) . ?
C6 C5 1.387(2) . ?
C4 C9 1.398(2) . ?
C4 C3 1.4595(19) . ?
C4 C5 1.400(2) . ?
C7 C8 1.389(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.387(2) . ?
C3 H3 0.9500 . ?
C3 C2 1.334(2) . ?
C5 H5 0.9500 . ?
C8 H8 0.9500 . ?
C1 C2 1.4569(19) . ?
C2 H2 0.9500 . ?

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 109.5 . . ?
C7 O4 H7 109.5 . . ?
C6 O3 H6 109.5 . . ?
O3 C6 C7 116.13(12) . . ?
O3 C6 C5 124.00(13) . . ?
C5 C6 C7 119.88(13) . . ?
C9 C4 C3 122.74(13) . . ?
C9 C4 C5 118.51(13) . . ?
C5 C4 C3 118.74(13) . . ?
O4 C7 C6 115.92(13) . . ?
O4 C7 C8 124.20(13) . . ?
C8 C7 C6 119.85(13) . . ?
C4 C9 H9 119.5 . . ?
C8 C9 C4 120.93(13) . . ?
C8 C9 H9 119.5 . . ?
C4 C3 H3 117.3 . . ?
C2 C3 C4 125.48(13) . . ?
C2 C3 H3 117.3 . . ?
C6 C5 C4 120.83(13) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 119.99(13) . . ?
C9 C8 H8 120.0 . . ?
O1 C1 C2 117.03(13) . . ?
O2 C1 O1 122.08(12) . . ?
O2 C1 C2 120.88(13) . . ?
C3 C2 C1 123.94(13) . . ?
C3 C2 H2 118.0 . . ?
C1 C2 H2 118.0 . . ?

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
O1 C1 C2 C3 -0.8(2) . . . . ?
O4 C7 C8 C9 177.60(13) . . . . ?
O2 C1 C2 C3 178.63(14) . . . . ?
O3 C6 C7 O4 2.95(18) . . . . ?
O3 C6 C7 C8 -178.98(12) . . . . ?
O3 C6 C5 C4 179.04(12) . . . . ?
C6 C7 C8 C9 -0.3(2) . . . . ?
C4 C9 C8 C7 -0.7(2) . . . . ?
C4 C3 C2 C1 -178.94(13) . . . . ?
C7 C6 C5 C4 -1.2(2) . . . . ?
C9 C4 C3 C2 -4.3(2) . . . . ?
C9 C4 C5 C6 0.2(2) . . . . ?
C3 C4 C9 C8 -178.78(13) . . . . ?
C3 C4 C5 C6 179.79(13) . . . . ?
C5 C6 C7 O4 -176.79(12) . . . . ?
C5 C6 C7 C8 1.3(2) . . . . ?
C5 C4 C9 C8 0.8(2) . . . . ?
C5 C4 C3 C2 176.18(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cu_zhiwang02_0m
_database_code_depnum_ccdc_archive 'CCDC 2021371'
loop_
_audit_author_name
_audit_author_address
'Angel Ugrinov'
;North Dakota State University
United States of America
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2020-10-26 downloaded from the CCDC.
;
_audit_creation_date             2020-06-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H10 O4'
_chemical_formula_sum            'C10 H10 O4'
_chemical_formula_weight         194.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.2043(3)
_cell_length_b                   11.5780(4)
_cell_length_c                   11.3815(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.771(3)
_cell_angle_gamma                90
_cell_volume                     913.61(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3197
_cell_measurement_temperature    107.24
_cell_measurement_theta_max      66.347
_cell_measurement_theta_min      5.560
_shelx_estimated_absorpt_T_max   0.923
_shelx_estimated_absorpt_T_min   0.866
_exptl_absorpt_coefficient_mu    0.929
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0862 before and 0.0613 after correction.
The Ratio of minimum to maximum transmission is 0.8506.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.088
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8341
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        66.752
_diffrn_reflns_theta_max         66.752
_diffrn_reflns_theta_min         5.560
_diffrn_ambient_temperature      107.24
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           0.64
_diffrn_source_power             0.0286976
_diffrn_source_voltage           44.84
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1297
_reflns_number_total             1597
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1597
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0591P)²+0.6684P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1311
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C008(H008), C009(H009), C00C(H00C), C00D(H00D)
2.b Idealised Me refined as rotating group:
 C00E(H00A,H00B,H00E)
2.c Idealised tetrahedral OH refined as rotating group:
 O002(H002), O004(H004)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.1529(2) 0.24575(13) 0.47971(13) 0.0234(4) Uani 1 1 d . . . . .
O3 O 0.3983(2) 0.87508(13) 0.43039(13) 0.0230(4) Uani 1 1 d . . . . .
H6 H 0.389538 0.846328 0.361334 0.035 Uiso 1 1 calc R U . . .
O2 O 0.1173(2) 0.27073(13) 0.28006(14) 0.0254(4) Uani 1 1 d . . . . .
O4 O 0.4514(3) 0.93353(13) 0.66787(14) 0.0272(4) Uani 1 1 d . . . . .
H7 H 0.471745 0.971287 0.609592 0.041 Uiso 1 1 calc R U . . .
C4 C 0.2967(3) 0.59592(19) 0.55832(19) 0.0189(5) Uani 1 1 d . . . . .
C5 C 0.3200(3) 0.67833(19) 0.4730(2) 0.0187(5) Uani 1 1 d . . . . .
H5 H 0.299144 0.656990 0.389845 0.022 Uiso 1 1 calc R U . . .
C6 C 0.3729(3) 0.78972(19) 0.50893(19) 0.0184(5) Uani 1 1 d . . . . .
C3 C 0.2435(3) 0.47648(19) 0.52433(19) 0.0196(5) Uani 1 1 d . . . . .
H3 H 0.235650 0.425608 0.588294 0.024 Uiso 1 1 calc R U . . .
C2 C 0.2047(3) 0.43159(19) 0.4122(2) 0.0206(5) Uani 1 1 d . . . . .
H2 H 0.210472 0.481532 0.347058 0.025 Uiso 1 1 calc R U . . .
C7 C 0.4031(3) 0.82245(19) 0.6312(2) 0.0201(5) Uani 1 1 d . . . . .
C1 C 0.1541(3) 0.31120(19) 0.38314(19) 0.0197(5) Uani 1 1 d . . . . .
C9 C 0.3272(3) 0.6297(2) 0.6796(2) 0.0225(5) Uani 1 1 d . . . . .
H9 H 0.311703 0.574888 0.738347 0.027 Uiso 1 1 calc R U . . .
C8 C 0.3799(3) 0.7420(2) 0.7158(2) 0.0232(5) Uani 1 1 d . . . . .
H8 H 0.399985 0.763714 0.798838 0.028 Uiso 1 1 calc R U . . .
C10 C 0.1044(4) 0.12586(19) 0.4538(2) 0.0267(6) Uani 1 1 d . . . . .
H10C H -0.024596 0.120169 0.396937 0.040 Uiso 1 1 calc R U . . .
H10B H 0.106137 0.085590 0.529843 0.040 Uiso 1 1 calc R U . . .
H10A H 0.198789 0.090353 0.417091 0.040 Uiso 1 1 calc R U . . .


_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 1.337(3) . ?
O1 C10 1.442(3) . ?
O3 H6 0.8400 . ?
O3 C6 1.378(3) . ?
O2 C1 1.224(3) . ?
O4 H7 0.8400 . ?
O4 C7 1.367(3) . ?
C4 C5 1.403(3) . ?
C4 C3 1.459(3) . ?
C4 C9 1.394(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.375(3) . ?
C6 C7 1.402(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.335(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.456(3) . ?
C7 C8 1.382(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.385(3) . ?
C8 H8 0.9500 . ?
C10 H10C 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10A 0.9800 . ?

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 C10 115.65(17) . . ?
C6 O3 H6 109.5 . . ?
C7 O4 H7 109.5 . . ?
C5 C4 C3 122.2(2) . . ?
C9 C4 C5 118.6(2) . . ?
C9 C4 C3 119.2(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.7 . . ?
O3 C6 C7 116.00(19) . . ?
C5 C6 O3 123.71(19) . . ?
C5 C6 C7 120.3(2) . . ?
C4 C3 H3 116.8 . . ?
C2 C3 C4 126.4(2) . . ?
C2 C3 H3 116.8 . . ?
C3 C2 H2 117.8 . . ?
C3 C2 C1 124.3(2) . . ?
C1 C2 H2 117.8 . . ?
O4 C7 C6 121.0(2) . . ?
O4 C7 C8 119.38(19) . . ?
C8 C7 C6 119.6(2) . . ?
O1 C1 C2 114.39(19) . . ?
O2 C1 O1 121.5(2) . . ?
O2 C1 C2 124.1(2) . . ?
C4 C9 H9 119.5 . . ?
C8 C9 C4 121.0(2) . . ?
C8 C9 H9 119.5 . . ?
C7 C8 C9 120.0(2) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
O1 C10 H10C 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10A 109.5 . . ?
H10C C10 H10B 109.5 . . ?
H10C C10 H10A 109.5 . . ?
H10B C10 H10A 109.5 . . ?

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
O3 C6 C7 O4 1.1(3) . . . . ?
O3 C6 C7 C8 179.8(2) . . . . ?
O4 C7 C8 C9 178.7(2) . . . . ?
C4 C5 C6 O3 -179.94(19) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
C4 C3 C2 C1 179.3(2) . . . . ?
C4 C9 C8 C7 -0.1(4) . . . . ?
C5 C4 C3 C2 -2.4(4) . . . . ?
C5 C4 C9 C8 -0.1(3) . . . . ?
C5 C6 C7 O4 -178.5(2) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C3 C4 C5 C6 -179.1(2) . . . . ?
C3 C4 C9 C8 179.3(2) . . . . ?
C3 C2 C1 O1 -1.4(3) . . . . ?
C3 C2 C1 O2 179.4(2) . . . . ?
C9 C4 C5 C6 0.4(3) . . . . ?
C9 C4 C3 C2 178.2(2) . . . . ?
C10 O1 C1 O2 -0.4(3) . . . . ?
C10 O1 C1 C2 -179.65(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_wan20_01
_database_code_depnum_ccdc_archive 'CCDC 2021374'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2020-10-26 downloaded from the CCDC.
;
_audit_creation_date             2020-07-22
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            CBDA10coEA
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 O8, 2(C4 H8 O2)'
_chemical_formula_sum            'C26 H32 O12'
_chemical_formula_weight         536.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 H32 O12 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.38820(10)
_cell_length_b                   8.4135(2)
_cell_length_c                   14.8002(4)
_cell_angle_alpha                77.600(2)
_cell_angle_beta                 80.086(2)
_cell_angle_gamma                88.273(2)
_cell_volume                     645.49(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    8140
_cell_measurement_temperature    100.00(13)
_cell_measurement_theta_max      77.2950
_cell_measurement_theta_min      5.3590
_shelx_estimated_absorpt_T_max   0.888
_shelx_estimated_absorpt_T_min   0.814
_exptl_absorpt_coefficient_mu    0.931
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.456
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             284
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -9 0.0928
3 -1 -5 0.1033
3 0 3 0.0668
-3 1 3 0.1007
0 1 10 0.0954
-3 0 -5 0.0619
0 1 -8 0.0712
0 -5 -2 0.0613
0 -4 4 0.0636
0 5 -1 0.0692
-1 2 -7 0.0688
-2 4 -3 0.0758
2 -5 1 0.0657
2 -4 5 0.0644
-2 2 -7 0.0622
-3 3 -4 0.0681
3 -3 2 0.0677
-3 -1 -7 0.0676
-3 -3 -4 0.0644
-1 0 8 0.0913
3 3 3 0.0758
-2 -5 -3 0.0622
2 4 0 0.0655
1 1 -8 0.0789
-2 -5 -2 0.0581
0 0 9 0.0822
-3 1 -5 0.0544

_exptl_crystal_recrystallization_method 
'Slow evaporation from a mixture of methanol and acetic acid at room temperature'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.131
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.1423 -1.4566 -9.3730 0.0385 0.1656 0.9854
2.7273 -1.0428 -4.5809 0.1987 0.8324 0.5174
3.4262 0.1037 3.4549 0.2213 0.9225 -0.3164
-3.0604 0.8518 3.0666 -0.2166 -0.9063 -0.3630
0.2854 1.4313 9.5555 -0.0102 -0.0472 -0.9988
-3.3179 -0.2828 -4.5336 -0.2106 -0.8774 0.4311
-0.2720 1.4520 -8.4668 0.4931 -0.1171 0.8621
-0.3209 -5.4456 -1.7465 -0.9481 0.2273 0.2225
-0.0265 -4.2479 4.2304 -0.8900 0.2127 -0.4033
0.2186 5.2376 -0.5693 0.9724 -0.2328 0.0180
-1.3792 2.2278 -7.3644 0.4984 -0.4714 0.7276
-1.5981 4.2037 -3.0651 0.7005 -0.6636 0.2628
1.5639 -4.6186 1.2965 -0.7237 0.6859 -0.0764
1.5788 -3.6838 4.6095 -0.6565 0.6216 -0.4274
-2.2503 1.5037 -7.0029 0.2797 -0.6723 0.6853
-2.6561 2.6849 -3.8985 0.3595 -0.8655 0.3487
2.6984 -3.2275 1.5620 -0.3813 0.9189 -0.1014
-2.9047 -0.6499 -6.6399 -0.1748 -0.7328 0.6576
-3.0062 -2.6956 -4.2664 -0.6216 -0.6565 0.4274
-1.3861 -0.1540 7.7999 -0.3900 -0.4102 -0.8244
3.1205 2.6053 2.6988 0.6636 0.7005 -0.2627
-1.9636 -4.5920 -3.2665 -0.8970 -0.2667 0.3525
1.9352 4.4038 0.0653 0.9585 0.2845 -0.0195
0.7577 1.4203 -7.8479 0.5611 0.1656 0.8110
-1.6774 -4.8646 -2.2104 -0.9522 -0.1773 0.2489
-0.0268 0.0100 9.2379 -0.2824 -0.0514 -0.9579
-3.0922 1.1547 -4.7000 0.0715 -0.8956 0.4391

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11740
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.852
_diffrn_reflns_theta_min         3.102
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00 123.00   0.50    0.05    --   47.70  22.00 -87.00  174
  2  ω     96.00 178.00   0.50    0.21    --  107.75  22.00 -87.00  164
  3  ω     95.00 178.00   0.50    0.21    --  107.75  30.00-120.00  166
  4  ω     95.00 178.00   0.50    0.21    --  107.75  45.00 -30.00  166
  5  ω     95.00 178.00   0.50    0.21    --  107.75 125.00 -30.00  166
  6  ω     95.00 170.00   0.50    0.21    --  107.75  30.00  60.00  150
  7  ω     94.00 178.00   0.50    0.21    --  107.75  15.00-180.00  168
  8  ω     34.00  95.00   0.50    0.05    --   47.70-125.00  30.00  122
  9  ω     35.00 112.00   0.50    0.21    --  107.75-125.00  90.00  154
 10  ω     35.00 106.00   0.50    0.21    --  107.75 -94.00  30.00  142
 11  ω     35.00  73.00   0.50    0.21    --  107.75 -61.00-120.00   76
 12  ω     35.00 106.00   0.50    0.21    --  107.75 -94.00-180.00  142
 13  ω     35.00  73.00   0.50    0.21    --  107.75 -61.00 -90.00   76
 14  ω     35.00 106.00   0.50    0.21    --  107.75 -94.00 -30.00  142
 15  ω     35.00  73.00   0.50    0.21    --  107.75 -61.00  60.00   76
 16  ω     35.00 105.00   0.50    0.21    --  107.75 -95.00 147.00  140
 17  ω     35.00 112.00   0.50    0.21    --  107.75-125.00 150.00  154
 18  ω     35.00 112.00   0.50    0.21    --  107.75-125.00 -30.00  154
 19  ω     35.00  73.00   0.50    0.21    --  107.75 -61.00 -60.00   76
 20  ω     35.00 106.00   0.50    0.21    --  107.75 -94.00 -90.00  142
 21  ω    -27.00  31.00   0.50    0.05    --   47.70 -22.00 106.00  116
 22  ω     25.00 120.00   0.50    0.05    --   47.70  77.00 150.00  190
 23  ω    -24.00  28.00   0.50    0.05    --  -47.70  19.00  30.00  104
 24  ω    -27.00  28.00   0.50    0.05    --  -47.70  22.00 -87.00  110
 25  ω    -49.00 -14.00   0.50    0.21    --  -86.25  45.00 -90.00   70
 26  ω    -49.00 -14.00   0.50    0.21    --  -86.25  45.00-180.00   70
 27  ω    -49.00 -14.00   0.50    0.21    --  -86.25  45.00   0.00   70
 28  ω    -69.00 -13.00   0.50    0.21    --  -86.25  61.00  60.00  112
 29  ω   -119.00 -25.00   0.50    0.05    --  -47.70 -77.00 -90.00  188
 30  ω   -119.00 -73.00   0.50    0.05    --  -47.70-125.00  30.00   92
 31  ω   -119.00 -33.00   0.50    0.05    --  -47.70 -57.00 -60.00  172
 32  ω   -122.00 -35.00   0.50    0.05    --  -47.70 -22.00 106.00  174
 33  ω   -121.00 -34.00   0.50    0.05    --  -47.70 -38.00  60.00  174
 34  ω   -119.00 -73.00   0.50    0.05    --  -47.70-125.00-120.00   92
 35  ω   -119.00 -25.00   0.50    0.05    --  -47.70 -77.00-150.00  188
 36  ω   -119.00 -25.00   0.50    0.05    --  -47.70 -77.00  30.00  188
 37  ω   -119.00 -33.00   0.50    0.05    --  -47.70 -57.00  60.00  172
 38  ω   -119.00 -25.00   0.50    0.05    --  -47.70 -77.00 -30.00  188
 39  ω   -159.00 -73.00   0.50    0.21    --  -86.25-125.00  60.00  172
 40  ω   -162.00 -74.00   0.50    0.21    --  -86.25 -22.00 106.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0899269000
_diffrn_orient_matrix_UB_12      0.1785812000
_diffrn_orient_matrix_UB_13      -0.0304981000
_diffrn_orient_matrix_UB_21      0.2756955000
_diffrn_orient_matrix_UB_22      -0.0564723000
_diffrn_orient_matrix_UB_23      -0.0047088000
_diffrn_orient_matrix_UB_31      0.0124199000
_diffrn_orient_matrix_UB_32      -0.0083495000
_diffrn_orient_matrix_UB_33      -0.1036499000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2413
_reflns_number_total             2628
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2628
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0479P)²+0.1760P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.0982
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C9(H9)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C13(H13A,H13B,H13C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.80477(17) 0.16536(10) 0.45175(6) 0.0266(2) Uani 1 1 d . . . . .
H1 H 0.837477 0.066487 0.453946 0.040 Uiso 1 1 calc R U . . .
O2 O 1.09111(17) 0.14203(10) 0.54702(6) 0.0244(2) Uani 1 1 d . . . . .
O3 O 0.83096(18) 0.43601(12) 0.91356(6) 0.0308(2) Uani 1 1 d . . . . .
H6 H 0.720341 0.458582 0.956249 0.046 Uiso 1 1 calc R U . . .
O4 O 0.40306(17) 0.61424(11) 0.90164(6) 0.0261(2) Uani 1 1 d . . . . .
H7 H 0.281202 0.674739 0.889162 0.039 Uiso 1 1 calc R U . . .
O5 O 0.67853(18) -0.02305(12) 0.85883(7) 0.0312(2) Uani 1 1 d . . . . .
O6 O 1.02883(17) -0.17119(11) 0.85927(7) 0.0301(2) Uani 1 1 d . . . . .
C2 C 0.8751(2) 0.39513(13) 0.51040(8) 0.0187(2) Uani 1 1 d . . . . .
H2 H 0.688728 0.408652 0.526152 0.022 Uiso 1 1 calc R U . . .
C3 C 1.0106(2) 0.46794(13) 0.57671(8) 0.0185(2) Uani 1 1 d . . . . .
H3 H 1.147103 0.393144 0.597620 0.022 Uiso 1 1 calc R U . . .
C1 C 0.9366(2) 0.22160(14) 0.50502(8) 0.0199(2) Uani 1 1 d . . . . .
C4 C 0.8465(2) 0.51287(14) 0.66062(8) 0.0186(2) Uani 1 1 d . . . . .
C5 C 0.9093(2) 0.45721(14) 0.74943(8) 0.0204(2) Uani 1 1 d . . . . .
H5 H 1.057153 0.394411 0.755894 0.024 Uiso 1 1 calc R U . . .
C6 C 0.7583(2) 0.49235(14) 0.82870(8) 0.0215(3) Uani 1 1 d . . . . .
C7 C 0.5403(2) 0.58386(14) 0.81994(8) 0.0205(2) Uani 1 1 d . . . . .
C8 C 0.4760(2) 0.64032(14) 0.73213(8) 0.0206(2) Uani 1 1 d . . . . .
H8 H 0.327999 0.703117 0.725872 0.025 Uiso 1 1 calc R U . . .
C9 C 0.6287(2) 0.60497(14) 0.65275(8) 0.0202(2) Uani 1 1 d . . . . .
H9 H 0.583666 0.644127 0.592629 0.024 Uiso 1 1 calc R U . . .
C10 C 0.7576(3) -0.16302(19) 1.00592(10) 0.0363(3) Uani 1 1 d . . . . .
H10B H 0.877272 -0.239176 1.034742 0.054 Uiso 1 1 calc R U . . .
H10A H 0.589658 -0.213195 1.020900 0.054 Uiso 1 1 calc R U . . .
H10C H 0.752194 -0.063327 1.030358 0.054 Uiso 1 1 calc R U . . .
C11 C 0.8397(2) -0.12239(16) 0.90182(9) 0.0266(3) Uani 1 1 d . . . . .
C12 C 0.7341(2) 0.02148(17) 0.75704(9) 0.0292(3) Uani 1 1 d . . . . .
H12A H 0.764824 -0.077006 0.730328 0.035 Uiso 1 1 calc R U . . .
H12B H 0.885593 0.092242 0.736166 0.035 Uiso 1 1 calc R U . . .
C13 C 0.5069(3) 0.1109(2) 0.72576(11) 0.0378(3) Uani 1 1 d . . . . .
H13A H 0.531963 0.138716 0.657023 0.057 Uiso 1 1 calc R U . . .
H13B H 0.483932 0.210832 0.750135 0.057 Uiso 1 1 calc R U . . .
H13C H 0.357050 0.041466 0.749785 0.057 Uiso 1 1 calc R U . . .


_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 H1 0.8400 . ?
O1 C1 1.3129(15) . ?
O2 C1 1.2220(14) . ?
O3 H6 0.8400 . ?
O3 C6 1.3629(14) . ?
O4 H7 0.8400 . ?
O4 C7 1.3739(14) . ?
O5 C11 1.3327(16) . ?
O5 C12 1.4521(16) . ?
O6 C11 1.2117(16) . ?
C2 H2 1.0000 . ?
C2 C3 1.5500(15) . ?
C2 C3 1.5812(15) 2_766 ?
C2 C1 1.5031(15) . ?
C3 H3 1.0000 . ?
C3 C4 1.5067(15) . ?
C4 C5 1.3932(16) . ?
C4 C9 1.3946(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3896(16) . ?
C6 C7 1.3947(17) . ?
C7 C8 1.3837(16) . ?
C8 H8 0.9500 . ?
C8 C9 1.3957(16) . ?
C9 H9 0.9500 . ?
C10 H10B 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10C 0.9800 . ?
C10 C11 1.4949(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5062(19) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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 109.5 . . ?
C6 O3 H6 109.5 . . ?
C7 O4 H7 109.5 . . ?
C11 O5 C12 117.06(10) . . ?
C3 C2 H2 110.2 . . ?
C3 C2 H2 110.2 2_766 . ?
C3 C2 C3 91.36(8) . 2_766 ?
C1 C2 H2 110.2 . . ?
C1 C2 C3 117.25(9) . 2_766 ?
C1 C2 C3 116.21(9) . . ?
C2 C3 C2 88.64(8) . 2_766 ?
C2 C3 H3 109.8 2_766 . ?
C2 C3 H3 109.8 . . ?
C4 C3 C2 120.34(9) . 2_766 ?
C4 C3 C2 116.63(9) . . ?
C4 C3 H3 109.8 . . ?
O1 C1 C2 112.80(10) . . ?
O2 C1 O1 124.17(11) . . ?
O2 C1 C2 123.02(10) . . ?
C5 C4 C3 119.28(10) . . ?
C5 C4 C9 118.61(10) . . ?
C9 C4 C3 122.08(10) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.85(11) . . ?
C6 C5 H5 119.6 . . ?
O3 C6 C5 118.15(10) . . ?
O3 C6 C7 121.88(11) . . ?
C5 C6 C7 119.97(11) . . ?
O4 C7 C6 116.23(10) . . ?
O4 C7 C8 123.96(11) . . ?
C8 C7 C6 119.80(11) . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 119.97(11) . . ?
C9 C8 H8 120.0 . . ?
C4 C9 C8 120.80(10) . . ?
C4 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
H10B C10 H10A 109.5 . . ?
H10B C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10C 109.5 . . ?
O5 C11 C10 111.89(11) . . ?
O6 C11 O5 122.41(12) . . ?
O6 C11 C10 125.70(12) . . ?
O5 C12 H12A 110.4 . . ?
O5 C12 H12B 110.4 . . ?
O5 C12 C13 106.44(11) . . ?
H12A C12 H12B 108.6 . . ?
C13 C12 H12A 110.4 . . ?
C13 C12 H12B 110.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
O1 H1 O2 0.84 1.79 2.6267(12) 177.4 2_756 yes
O3 H6 O4 0.84 2.28 2.7228(12) 113.6 . yes
O3 H6 O4 0.84 2.06 2.7564(12) 140.4 2_667 yes
O4 H7 O6 0.84 1.89 2.7291(12) 174.3 1_465 yes

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
O3 C6 C7 O4 0.11(18) . . . . ?
O3 C6 C7 C8 179.12(11) . . . . ?
O4 C7 C8 C9 179.22(11) . . . . ?
C2 C3 C4 C5 -125.35(12) 2_766 . . . ?
C2 C3 C4 C5 129.41(11) . . . . ?
C2 C3 C4 C9 56.51(16) 2_766 . . . ?
C2 C3 C4 C9 -48.73(15) . . . . ?
C3 C2 C3 C2 0.000(1) 2_766 . . 2_766 ?
C3 C2 C3 C4 123.59(11) 2_766 . . . ?
C3 C2 C1 O1 -77.13(13) 2_766 . . . ?
C3 C2 C1 O1 176.41(10) . . . . ?
C3 C2 C1 O2 103.69(13) 2_766 . . . ?
C3 C2 C1 O2 -2.76(16) . . . . ?
C3 C4 C5 C6 -178.15(10) . . . . ?
C3 C4 C9 C8 177.93(10) . . . . ?
C1 C2 C3 C2 121.48(11) . . . 2_766 ?
C1 C2 C3 C4 -114.93(11) . . . . ?
C4 C5 C6 O3 -179.31(11) . . . . ?
C4 C5 C6 C7 0.28(18) . . . . ?
C5 C4 C9 C8 -0.22(17) . . . . ?
C5 C6 C7 O4 -179.46(10) . . . . ?
C5 C6 C7 C8 -0.45(18) . . . . ?
C6 C7 C8 C9 0.29(18) . . . . ?
C7 C8 C9 C4 0.05(18) . . . . ?
C9 C4 C5 C6 0.06(17) . . . . ?
C11 O5 C12 C13 171.38(12) . . . . ?
C12 O5 C11 O6 1.96(19) . . . . ?
C12 O5 C11 C10 -178.21(12) . . . . ?

loop_
_audit_author_email
zhihan.wang@enmu.edu
daniel.unruh@ttu.edu
_olex2_date_sample_data_collection 2020-07-21
_olex2_date_sample_submission    2020-07-21
_olex2_exptl_crystal_mounting_method 'MiTeGen 50 micron loop'
_olex2_submission_original_sample_id CBDAS1
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.653
_oxdiff_exptl_absorpt_empirical_full_min 0.728
_vrf_PLAT911_wan20_01            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report
RESPONSE: These inconsistent reflections were omitted during the integration.
;
####################################################################### 
# 
# 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_cu_zhiwang03_0m
_database_code_depnum_ccdc_archive 'CCDC 2021372'
loop_
_audit_author_name
_audit_author_address
'Angel Ugrinov'
;North Dakota State University
United States of America
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2020-10-26 downloaded from the CCDC.
;
_audit_creation_date             2020-06-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            CBDE-10
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 O8'
_chemical_formula_sum            'C20 H20 O8'
_chemical_formula_weight         388.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.841(3)
_cell_length_b                   10.807(3)
_cell_length_c                   9.978(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.64(2)
_cell_angle_gamma                90
_cell_volume                     879.9(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2427
_cell_measurement_temperature    107.02
_cell_measurement_theta_max      66.356
_cell_measurement_theta_min      6.311
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.868
_exptl_absorpt_coefficient_mu    0.964
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1617 before and 0.0808 after correction.
The Ratio of minimum to maximum transmission is 0.6343.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.151
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.077
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1206
_diffrn_reflns_av_unetI/netI     0.0941
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6758
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        66.890
_diffrn_reflns_theta_max         66.890
_diffrn_reflns_theta_min         5.421
_diffrn_ambient_temperature      107.02
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           0.64
_diffrn_source_power             0.0286976
_diffrn_source_voltage           44.84
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                925
_reflns_number_total             1519
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1519
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1418
_refine_ls_R_factor_gt           0.0919
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0467P)²+5.1438P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2103
_refine_ls_wR_factor_ref         0.2311
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00A(H00A), C00D(H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C009(H009), C00B(H00B)
2.c Idealised Me refined as rotating group:
 C00E(H00C,H00E,H00F)
2.d Idealised tetrahedral OH refined as rotating group:
 O001(H001), O004(H004)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O4 O 0.4708(5) 0.2359(3) 0.7118(5) 0.0297(11) Uani 1 1 d . . . . .
H7 H 0.408094 0.283004 0.733442 0.045 Uiso 1 1 calc R U . . .
O1 O 0.8940(5) 0.5291(4) 0.1519(5) 0.0324(11) Uani 1 1 d . . . . .
O2 O 0.8169(5) 0.6793(4) 0.2674(5) 0.0317(11) Uani 1 1 d . . . . .
O3 O 0.4957(5) 0.4831(4) 0.7619(5) 0.0348(11) Uani 1 1 d . . . . .
H6 H 0.511309 0.559858 0.770128 0.052 Uiso 1 1 calc R U . . .
C7 C 0.5738(6) 0.3059(5) 0.6672(6) 0.0241(13) Uani 1 1 d . . . . .
C5 C 0.6905(7) 0.5008(5) 0.6449(6) 0.0244(13) Uani 1 1 d . . . . .
H5 H 0.698834 0.587826 0.659692 0.029 Uiso 1 1 calc R U . . .
C6 C 0.5889(7) 0.4328(5) 0.6931(7) 0.0258(14) Uani 1 1 d . . . . .
C4 C 0.7803(7) 0.4437(5) 0.5753(7) 0.0274(14) Uani 1 1 d . . . . .
C8 C 0.6621(7) 0.2473(5) 0.5996(7) 0.0278(14) Uani 1 1 d . . . . .
H8 H 0.653017 0.160375 0.584643 0.033 Uiso 1 1 calc R U . . .
C3 C 0.8901(7) 0.5228(5) 0.5250(7) 0.0264(14) Uani 1 1 d . . . . .
H3 H 0.852879 0.610891 0.515753 0.032 Uiso 1 1 calc R U . . .
C9 C 0.7650(7) 0.3162(5) 0.5531(7) 0.0285(14) Uani 1 1 d . . . . .
H9 H 0.825862 0.275902 0.505452 0.034 Uiso 1 1 calc R U . . .
C1 C 0.8683(7) 0.5753(5) 0.2649(7) 0.0287(15) Uani 1 1 d . . . . .
C2 C 0.9170(7) 0.4837(6) 0.3874(7) 0.0296(15) Uani 1 1 d . . . . .
H2 H 0.869753 0.399948 0.352997 0.036 Uiso 1 1 calc R U . . .
C10 C 0.8673(9) 0.6146(7) 0.0324(8) 0.0443(19) Uani 1 1 d . . . . .
H10B H 0.870327 0.569245 -0.051510 0.066 Uiso 1 1 calc R U . . .
H10A H 0.953362 0.677849 0.062110 0.066 Uiso 1 1 calc R U . . .
H10C H 0.760096 0.654432 0.006208 0.066 Uiso 1 1 calc R U . . .


_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
O4 H7 0.8400 . ?
O4 C7 1.383(7) . ?
O1 C1 1.330(7) . ?
O1 C10 1.454(8) . ?
O2 C1 1.215(7) . ?
O3 H6 0.8400 . ?
O3 C6 1.371(7) . ?
C7 C6 1.392(8) . ?
C7 C8 1.367(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(8) . ?
C5 C4 1.385(8) . ?
C4 C3 1.516(8) . ?
C4 C9 1.395(8) . ?
C8 H8 0.9500 . ?
C8 C9 1.386(8) . ?
C3 H3 1.0000 . ?
C3 C2 1.591(8) 3_766 ?
C3 C2 1.540(8) . ?
C9 H9 0.9500 . ?
C1 C2 1.502(9) . ?
C2 H2 1.0000 . ?
C10 H10B 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10C 0.9800 . ?

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
C7 O4 H7 109.5 . . ?
C1 O1 C10 115.4(5) . . ?
C6 O3 H6 109.5 . . ?
O4 C7 C6 120.5(5) . . ?
C8 C7 O4 118.5(5) . . ?
C8 C7 C6 121.0(5) . . ?
C6 C5 H5 119.6 . . ?
C6 C5 C4 120.8(5) . . ?
C4 C5 H5 119.6 . . ?
O3 C6 C7 116.8(5) . . ?
O3 C6 C5 124.0(5) . . ?
C5 C6 C7 119.2(5) . . ?
C5 C4 C3 118.6(5) . . ?
C5 C4 C9 118.7(6) . . ?
C9 C4 C3 122.7(6) . . ?
C7 C8 H8 120.4 . . ?
C7 C8 C9 119.3(5) . . ?
C9 C8 H8 120.4 . . ?
C4 C3 H3 109.7 . . ?
C4 C3 C2 118.8(5) . 3_766 ?
C4 C3 C2 118.6(5) . . ?
C2 C3 H3 109.7 . . ?
C2 C3 H3 109.7 3_766 . ?
C2 C3 C2 88.7(5) . 3_766 ?
C4 C9 H9 119.5 . . ?
C8 C9 C4 120.9(6) . . ?
C8 C9 H9 119.5 . . ?
O1 C1 C2 110.7(5) . . ?
O2 C1 O1 123.5(6) . . ?
O2 C1 C2 125.8(6) . . ?
C3 C2 C3 91.3(5) . 3_766 ?
C3 C2 H2 111.5 3_766 . ?
C3 C2 H2 111.5 . . ?
C1 C2 C3 116.8(5) . . ?
C1 C2 C3 112.8(5) . 3_766 ?
C1 C2 H2 111.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10B C10 H10A 109.5 . . ?
H10B C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?

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
O4 C7 C6 O3 -0.9(8) . . . . ?
O4 C7 C6 C5 -178.8(5) . . . . ?
O4 C7 C8 C9 179.5(5) . . . . ?
O1 C1 C2 C3 -178.5(5) . . . . ?
O1 C1 C2 C3 77.7(6) . . . 3_766 ?
O2 C1 C2 C3 -100.2(7) . . . 3_766 ?
O2 C1 C2 C3 3.6(9) . . . . ?
C7 C8 C9 C4 0.5(9) . . . . ?
C5 C4 C3 C2 -148.2(6) . . . . ?
C5 C4 C3 C2 106.1(7) . . . 3_766 ?
C5 C4 C9 C8 0.0(9) . . . . ?
C6 C7 C8 C9 -1.6(9) . . . . ?
C6 C5 C4 C3 -179.9(5) . . . . ?
C6 C5 C4 C9 0.7(9) . . . . ?
C4 C5 C6 O3 -179.6(6) . . . . ?
C4 C5 C6 C7 -1.8(9) . . . . ?
C4 C3 C2 C3 -122.4(6) . . . 3_766 ?
C4 C3 C2 C1 121.2(6) . . . . ?
C8 C7 C6 O3 -179.8(5) . . . . ?
C8 C7 C6 C5 2.3(9) . . . . ?
C3 C4 C9 C8 -179.4(6) . . . . ?
C9 C4 C3 C2 31.2(9) . . . . ?
C9 C4 C3 C2 -74.5(8) . . . 3_766 ?
C2 C3 C2 C3 0.000(2) 3_766 . . 3_766 ?
C2 C3 C2 C1 -116.4(6) 3_766 . . . ?
C10 O1 C1 O2 4.1(8) . . . . ?
C10 O1 C1 C2 -173.9(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
