# Supplementary Information (SI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 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_z_sq
_database_code_depnum_ccdc_archive 'CCDC 2358377'
loop_
_audit_author_name
_audit_author_address
'Wang Yubo'
;Zhejiang University
China
;
_audit_update_record             
;
2024-05-27 deposited with the CCDC.	2024-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H10 N0 O8'
_chemical_formula_weight         354.26

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'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.824(2)
_cell_length_b                   14.235(4)
_cell_length_c                   14.278(3)
_cell_angle_alpha                70.00(3)
_cell_angle_beta                 88.62(2)
_cell_angle_gamma                76.31(2)
_cell_volume                     1263.8(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    215(2)
_cell_measurement_reflns_used    1273
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      58.47

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.931
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.642
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5060
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      215(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14348
_diffrn_reflns_av_unetI/netI     0.2087
_diffrn_reflns_av_R_equivalents  0.1904
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.300
_diffrn_reflns_theta_max         58.918
_diffrn_reflns_theta_full        58.918
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3600
_reflns_number_gt                1617
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0241P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3600
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1400
_refine_ls_R_factor_gt           0.0768
_refine_ls_wR_factor_ref         0.2451
_refine_ls_wR_factor_gt          0.1997
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_restrained_S_all      0.961
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O8 O 0.2040(5) 0.5309(2) 0.0557(2) 0.0615(10) Uani 1 1 d . . . . .
O7 O 0.3572(5) 0.3799(3) 0.0401(2) 0.0665(11) Uani 1 1 d . . . . .
H7A H 0.326062 0.414460 -0.019766 0.100 Uiso 1 1 calc R U . . .
O6 O 0.6509(5) 0.0830(2) 0.3363(2) 0.0657(11) Uani 1 1 d . . . . .
O5 O 0.6342(5) 0.0985(2) 0.4852(2) 0.0554(9) Uani 1 1 d . . . . .
H5A H 0.705193 0.038655 0.501553 0.083 Uiso 1 1 calc R U . . .
O1 O -0.1261(6) 0.8949(3) 0.4160(3) 0.0710(11) Uani 1 1 d . . . . .
H1A H -0.197811 0.954557 0.399385 0.106 Uiso 1 1 calc R U . . .
O2 O -0.1445(5) 0.9104(2) 0.5664(2) 0.0530(9) Uani 1 1 d . . . . .
O4 O 0.2886(5) 0.4593(2) 0.8459(2) 0.0604(10) Uani 1 1 d . . . . .
O3 O 0.1392(5) 0.6113(2) 0.8617(2) 0.0545(9) Uani 1 1 d . . . . .
H3A H 0.168378 0.576921 0.921774 0.082 Uiso 1 1 calc R U . . .
C4 C 0.3009(7) 0.4359(3) 0.0920(3) 0.0434(11) Uani 1 1 d . . . . .
C8 C 0.2174(6) 0.5414(3) 0.6414(3) 0.0370(10) Uani 1 1 d . . . . .
H8A H 0.285067 0.471603 0.670774 0.044 Uiso 1 1 calc R U . . .
C17 C 0.3432(6) 0.3905(3) 0.2030(3) 0.0409(11) Uani 1 1 d . . . . .
C16 C 0.4405(6) 0.2865(3) 0.2443(3) 0.0414(11) Uani 1 1 d . . . . .
H16A H 0.475519 0.245527 0.204096 0.050 Uiso 1 1 calc R U . . .
C15 C 0.4845(6) 0.2451(3) 0.3477(3) 0.0373(10) Uani 1 1 d . . . . .
C14 C 0.4294(6) 0.3040(3) 0.4070(3) 0.0357(10) Uani 1 1 d . . . . .
H14A H 0.456779 0.274226 0.476551 0.043 Uiso 1 1 calc R U . . .
C13 C 0.3318(6) 0.4091(3) 0.3636(3) 0.0428(11) Uani 1 1 d . . . . .
C18 C 0.2911(6) 0.4517(3) 0.2601(3) 0.0385(10) Uani 1 1 d . . . . .
H18A H 0.228239 0.522110 0.229797 0.046 Uiso 1 1 calc R U . . .
C12 C 0.2824(6) 0.4722(3) 0.4243(3) 0.0402(11) Uani 1 1 d . . . . .
C11 C 0.2369(6) 0.5235(3) 0.4762(3) 0.0366(10) Uani 1 1 d . . . . .
C9 C 0.1785(6) 0.5851(3) 0.5364(3) 0.0386(10) Uani 1 1 d . . . . .
C10 C 0.0814(6) 0.6921(3) 0.4939(3) 0.0411(11) Uani 1 1 d . . . . .
H10A H 0.058678 0.723666 0.424254 0.049 Uiso 1 1 calc R U . . .
C5 C 0.0215(6) 0.7489(3) 0.5547(3) 0.0420(11) Uani 1 1 d . . . . .
C6 C 0.0624(6) 0.7062(3) 0.6567(3) 0.0400(10) Uani 1 1 d . . . . .
H6A H 0.027568 0.747394 0.696729 0.048 Uiso 1 1 calc R U . . .
C7 C 0.1571(6) 0.6000(3) 0.7007(3) 0.0383(10) Uani 1 1 d . . . . .
C2 C 0.1975(7) 0.5547(4) 0.8104(3) 0.0439(11) Uani 1 1 d . . . . .
C1 C -0.0880(7) 0.8598(3) 0.5088(3) 0.0460(11) Uani 1 1 d . . . . .
C3 C 0.5960(6) 0.1342(3) 0.3920(3) 0.0448(11) Uani 1 1 d . . . . .


_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
O8 C4 1.284(5) . ?
O7 C4 1.257(5) . ?
O7 H7A 0.8300 . ?
O6 C3 1.248(5) . ?
O5 C3 1.260(5) . ?
O5 H5A 0.8300 . ?
O1 C1 1.255(6) . ?
O1 H1A 0.8300 . ?
O2 C1 1.267(5) . ?
O4 C2 1.277(5) . ?
O3 C2 1.258(5) . ?
O3 H3A 0.8300 . ?
C4 C17 1.499(6) . ?
C8 C7 1.373(6) . ?
C8 C9 1.417(6) . ?
C8 H8A 0.9400 . ?
C17 C18 1.369(6) . ?
C17 C16 1.391(6) . ?
C16 C15 1.400(6) . ?
C16 H16A 0.9400 . ?
C15 C14 1.373(6) . ?
C15 C3 1.497(6) . ?
C14 C13 1.407(6) . ?
C14 H14A 0.9400 . ?
C13 C18 1.399(6) . ?
C13 C12 1.431(6) . ?
C18 H18A 0.9400 . ?
C12 C11 1.195(5) . ?
C11 C9 1.415(6) . ?
C9 C10 1.427(6) . ?
C10 C5 1.371(6) . ?
C10 H10A 0.9400 . ?
C5 C6 1.379(6) . ?
C5 C1 1.496(6) . ?
C6 C7 1.416(6) . ?
C6 H6A 0.9400 . ?
C7 C2 1.480(6) . ?

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
C4 O7 H7A 109.5 . . ?
C3 O5 H5A 109.5 . . ?
C1 O1 H1A 109.5 . . ?
C2 O3 H3A 109.5 . . ?
O7 C4 O8 123.7(4) . . ?
O7 C4 C17 119.3(4) . . ?
O8 C4 C17 117.1(4) . . ?
C7 C8 C9 120.6(4) . . ?
C7 C8 H8A 119.7 . . ?
C9 C8 H8A 119.7 . . ?
C18 C17 C16 122.1(4) . . ?
C18 C17 C4 119.9(4) . . ?
C16 C17 C4 117.9(4) . . ?
C17 C16 C15 117.7(4) . . ?
C17 C16 H16A 121.1 . . ?
C15 C16 H16A 121.1 . . ?
C14 C15 C16 121.4(4) . . ?
C14 C15 C3 120.7(4) . . ?
C16 C15 C3 117.9(4) . . ?
C15 C14 C13 119.9(4) . . ?
C15 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
C18 C13 C14 119.1(4) . . ?
C18 C13 C12 120.6(4) . . ?
C14 C13 C12 120.2(4) . . ?
C17 C18 C13 119.7(4) . . ?
C17 C18 H18A 120.2 . . ?
C13 C18 H18A 120.2 . . ?
C11 C12 C13 178.1(4) . . ?
C12 C11 C9 178.6(4) . . ?
C11 C9 C8 120.2(4) . . ?
C11 C9 C10 121.5(4) . . ?
C8 C9 C10 118.3(4) . . ?
C5 C10 C9 120.0(4) . . ?
C5 C10 H10A 120.0 . . ?
C9 C10 H10A 120.0 . . ?
C10 C5 C6 121.4(4) . . ?
C10 C5 C1 119.0(4) . . ?
C6 C5 C1 119.6(4) . . ?
C5 C6 C7 119.6(4) . . ?
C5 C6 H6A 120.2 . . ?
C7 C6 H6A 120.2 . . ?
C8 C7 C6 120.0(4) . . ?
C8 C7 C2 120.8(4) . . ?
C6 C7 C2 119.2(4) . . ?
O3 C2 O4 124.8(4) . . ?
O3 C2 C7 118.6(4) . . ?
O4 C2 C7 116.6(4) . . ?
O1 C1 O2 124.5(4) . . ?
O1 C1 C5 117.5(4) . . ?
O2 C1 C5 118.0(4) . . ?
O6 C3 O5 123.4(4) . . ?
O6 C3 C15 119.7(4) . . ?
O5 C3 C15 116.9(4) . . ?

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
O7 C4 C17 C18 177.0(4) . . . . ?
O8 C4 C17 C18 -4.4(7) . . . . ?
O7 C4 C17 C16 -1.3(7) . . . . ?
O8 C4 C17 C16 177.3(4) . . . . ?
C18 C17 C16 C15 0.1(7) . . . . ?
C4 C17 C16 C15 178.3(4) . . . . ?
C17 C16 C15 C14 1.6(6) . . . . ?
C17 C16 C15 C3 -177.8(4) . . . . ?
C16 C15 C14 C13 -1.9(6) . . . . ?
C3 C15 C14 C13 177.5(4) . . . . ?
C15 C14 C13 C18 0.5(6) . . . . ?
C15 C14 C13 C12 -177.1(4) . . . . ?
C16 C17 C18 C13 -1.5(7) . . . . ?
C4 C17 C18 C13 -179.7(4) . . . . ?
C14 C13 C18 C17 1.2(7) . . . . ?
C12 C13 C18 C17 178.7(4) . . . . ?
C7 C8 C9 C11 -178.5(4) . . . . ?
C7 C8 C9 C10 2.1(6) . . . . ?
C11 C9 C10 C5 178.1(4) . . . . ?
C8 C9 C10 C5 -2.5(6) . . . . ?
C9 C10 C5 C6 3.5(7) . . . . ?
C9 C10 C5 C1 -177.3(4) . . . . ?
C10 C5 C6 C7 -4.0(7) . . . . ?
C1 C5 C6 C7 176.9(4) . . . . ?
C9 C8 C7 C6 -2.6(6) . . . . ?
C9 C8 C7 C2 -180.0(4) . . . . ?
C5 C6 C7 C8 3.5(6) . . . . ?
C5 C6 C7 C2 -179.1(4) . . . . ?
C8 C7 C2 O3 -179.9(4) . . . . ?
C6 C7 C2 O3 2.7(6) . . . . ?
C8 C7 C2 O4 -0.5(6) . . . . ?
C6 C7 C2 O4 -178.0(4) . . . . ?
C10 C5 C1 O1 2.4(7) . . . . ?
C6 C5 C1 O1 -178.4(4) . . . . ?
C10 C5 C1 O2 179.0(4) . . . . ?
C6 C5 C1 O2 -1.8(7) . . . . ?
C14 C15 C3 O6 -177.5(4) . . . . ?
C16 C15 C3 O6 1.8(6) . . . . ?
C14 C15 C3 O5 0.6(6) . . . . ?
C16 C15 C3 O5 179.9(4) . . . . ?

_refine_diff_density_max         0.329
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.054




####################################################################### 
# 
# 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_z_sq_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2358378'
loop_
_audit_author_name
_audit_author_address
'Wang Yubo'
;Zhejiang University
China
;
_audit_update_record             
;
2024-05-27 deposited with the CCDC.	2024-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H10 N0 O8'
_chemical_formula_weight         354.26

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'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'I 2/m'
_space_group_name_Hall           '-I 2y'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   3.6464(3)
_cell_length_b                   16.4377(14)
_cell_length_c                   20.954(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.582(6)
_cell_angle_gamma                90
_cell_volume                     1255.47(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    5016
_cell_measurement_theta_min      3.42
_cell_measurement_theta_max      68.31

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.937
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.646
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5763
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5349
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.418
_diffrn_reflns_theta_max         68.278
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1198
_reflns_number_gt                1080
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1341P)²+0.5534P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1198
_refine_ls_number_parameters     64
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0697
_refine_ls_wR_factor_ref         0.1957
_refine_ls_wR_factor_gt          0.1915
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.4942(4) 0.21632(8) 0.18238(6) 0.0472(5) Uani 1 1 d . . . . .
H1B H 0.578790 0.256877 0.202233 0.071 Uiso 1 1 calc R U . . .
O2 O 0.7704(4) 0.14981(8) 0.26326(6) 0.0445(5) Uani 1 1 d . . . . .
C4 C 0.2387(6) 0.000000 0.08853(11) 0.0305(6) Uani 1 2 d S T P . .
C6 C 0.5939(5) 0.15066(10) 0.21172(9) 0.0345(5) Uani 1 1 d . . . . .
C2 C 0.4887(4) 0.07303(9) 0.17989(8) 0.0316(5) Uani 1 1 d . . . . .
C1 C 0.5711(6) 0.000000 0.21049(11) 0.0316(6) Uani 1 2 d S T P . .
H1A H 0.682777 0.000002 0.251986 0.038 Uiso 1 2 calc R U P . .
C5 C 0.0711(6) 0.000000 0.02631(11) 0.0322(6) Uani 1 2 d S T P . .
C3 C 0.3240(5) 0.07333(10) 0.11926(8) 0.0329(5) Uani 1 1 d . . . . .
H3A H 0.269126 0.123532 0.098663 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 C6 1.290(2) . ?
O1 H1B 0.8400 . ?
O2 C6 1.242(2) . ?
C4 C3 1.397(2) 6 ?
C4 C3 1.398(2) . ?
C4 C5 1.425(3) . ?
C6 C2 1.485(2) . ?
C2 C1 1.3898(19) . ?
C2 C3 1.390(2) . ?
C1 H1A 0.9500 . ?
C5 C5 1.206(5) 5 ?
C3 H3A 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
C6 O1 H1B 109.5 . . ?
C3 C4 C3 119.2(2) 6 . ?
C3 C4 C5 120.40(10) 6 . ?
C3 C4 C5 120.40(10) . . ?
O2 C6 O1 123.81(15) . . ?
O2 C6 C2 120.13(14) . . ?
O1 C6 C2 116.05(16) . . ?
C1 C2 C3 120.47(15) . . ?
C1 C2 C6 119.02(16) . . ?
C3 C2 C6 120.46(15) . . ?
C2 C1 C2 119.5(2) . 6 ?
C2 C1 H1A 120.3 . . ?
C2 C1 H1A 120.3 6 . ?
C5 C5 C4 179.9(3) 5 . ?
C2 C3 C4 120.19(15) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C6 C2 C1 3.9(3) . . . . ?
O1 C6 C2 C1 -176.72(17) . . . . ?
O2 C6 C2 C3 -173.50(16) . . . . ?
O1 C6 C2 C3 5.9(3) . . . . ?
C3 C2 C1 C2 0.3(3) . . . 6 ?
C6 C2 C1 C2 -177.13(13) . . . 6 ?
C1 C2 C3 C4 0.1(3) . . . . ?
C6 C2 C3 C4 177.49(16) . . . . ?
C3 C4 C3 C2 -0.5(3) 6 . . . ?
C5 C4 C3 C2 -179.77(17) . . . . ?

_refine_diff_density_max         0.482
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.078




