# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_ZNZ7811
_database_code_depnum_ccdc_archive 'CCDC 1965075'
loop_
_audit_author_name
_audit_author_address
'Yi-Chen Tao'
;Soochow University
China
;
_audit_update_record             
;
2019-11-12 deposited with the CCDC.	2020-07-21 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H8 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         240.20

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   6.0211(4)
_cell_length_b                   5.2723(4)
_cell_length_c                   15.6347(12)
_cell_angle_alpha                90
_cell_angle_beta                 94.048(4)
_cell_angle_gamma                90
_cell_volume                     495.09(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    203
_cell_measurement_theta_min      14.7331
_cell_measurement_theta_max      51.8649
_cell_measurement_temperature    193.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             248

_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.88

_exptl_special_details           
;
;

_diffrn_ambient_temperature      193.(2)

_diffrn_source                   MetalJet
_diffrn_source_type              'Liquid Metal source'

_diffrn_radiation_type           ' Ga K\a'
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'

_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            4085
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_theta_min         4.93
_diffrn_reflns_theta_max         52.99
_diffrn_reflns_theta_full        52.99
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             870
_reflns_number_gt                761
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1361
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_number_reflns         870
_refine_ls_number_parameters     85
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0922P)²+0.1157P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.243
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.38A (Bruker Nano, Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker Nano, Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 946)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 1.31876(18) 0.1445(2) 0.51951(7) 0.0336(6) Uani d . . . 1 . .
O O2 0.49491(17) 0.6891(2) 0.61506(7) 0.0331(6) Uani d . . . 1 . .
H H2A 0.51097 0.788833 0.574068 0.05 Uiso calc U . R 1 . .
C C1 0.6688(2) 0.3471(3) 0.68786(10) 0.0297(6) Uani d . . . 1 . .
H H1 0.556419 0.351809 0.727537 0.036 Uiso calc U . R 1 . .
C C2 0.6632(2) 0.5211(3) 0.62044(10) 0.0271(6) Uani d . . . 1 . .
C C3 0.8299(2) 0.5125(3) 0.56120(9) 0.0246(6) Uani d . . . 1 . .
C C4 1.1740(2) 0.3088(3) 0.51016(10) 0.0252(6) Uani d . . . 1 . .
C C5 0.9973(2) 0.3265(3) 0.57218(10) 0.0243(6) Uani d . . . 1 . .
C C6 1.0009(2) 0.1563(3) 0.63936(10) 0.0283(6) Uani d . . . 1 . .
H H3 1.114825 0.031694 0.646089 0.034 Uiso calc U . R 1 . .
C C7 0.8351(3) 0.1694(3) 0.69731(10) 0.0311(6) Uani d . . . 1 . .
H H2 0.837503 0.053697 0.743939 0.037 Uiso calc U . R 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0317(8) 0.0349(8) 0.0349(8) 0.0123(5) 0.0077(5) 0.0047(5)
O2 0.0288(8) 0.0378(8) 0.0338(8) 0.0085(5) 0.0103(5) 0.0035(5)
C1 0.0268(9) 0.0365(10) 0.0265(10) -0.0028(6) 0.0069(6) 0.0003(7)
C2 0.0233(9) 0.0298(10) 0.0284(9) -0.0001(6) 0.0026(6) -0.0050(7)
C3 0.0229(9) 0.0269(9) 0.0242(9) 0.0000(6) 0.0021(6) -0.0023(7)
C4 0.0233(8) 0.0251(9) 0.0270(10) 0.0016(6) 0.0006(6) -0.0029(6)
C5 0.0236(9) 0.0256(9) 0.0236(9) -0.0009(6) 0.0010(6) -0.0018(6)
C6 0.0263(9) 0.0287(10) 0.0297(10) 0.0022(6) 0.0010(6) 0.0009(6)
C7 0.0324(10) 0.0333(10) 0.0277(10) -0.0032(6) 0.0034(7) 0.0043(7)

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 . 1.2301(18) ?
O2 C2 . 1.3438(18) ?
O2 H2A . 0.84 ?
C1 C7 . 1.371(2) ?
C1 C2 . 1.396(2) ?
C1 H1 . 0.95 ?
C2 C3 . 1.413(2) ?
C3 C5 . 1.408(2) ?
C3 C4 3_766 1.459(2) ?
C4 C5 . 1.492(2) ?
C5 C6 . 1.380(2) ?
C6 C7 . 1.397(2) ?
C6 H3 . 0.95 ?
C7 H2 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O2 H2A . . 109.5 ?
C7 C1 C2 . . 120.57(14) ?
C7 C1 H1 . . 119.7 ?
C2 C1 H1 . . 119.7 ?
O2 C2 C1 . . 117.25(13) ?
O2 C2 C3 . . 123.19(14) ?
C1 C2 C3 . . 119.55(14) ?
C5 C3 C2 . . 118.54(14) ?
C5 C3 C4 . 3_766 121.03(13) ?
C2 C3 C4 . 3_766 120.43(14) ?
O1 C4 C3 . 3_766 121.22(14) ?
O1 C4 C5 . . 119.89(14) ?
C3 C4 C5 3_766 . 118.89(13) ?
C6 C5 C3 . . 121.21(14) ?
C6 C5 C4 . . 118.71(14) ?
C3 C5 C4 . . 120.08(14) ?
C5 C6 C7 . . 119.19(14) ?
C5 C6 H3 . . 120.4 ?
C7 C6 H3 . . 120.4 ?
C1 C7 C6 . . 120.93(14) ?
C1 C7 H2 . . 119.5 ?
C6 C7 H2 . . 119.5 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 C1 C2 O2 . . . . 179.77(14) ?
C7 C1 C2 C3 . . . . 0.4(2) ?
O2 C2 C3 C5 . . . . -179.18(13) ?
C1 C2 C3 C5 . . . . 0.1(2) ?
O2 C2 C3 C4 . . . 3_766 0.1(2) ?
C1 C2 C3 C4 . . . 3_766 179.45(13) ?
C2 C3 C5 C6 . . . . -0.4(2) ?
C4 C3 C5 C6 3_766 . . . -179.67(13) ?
C2 C3 C5 C4 . . . . 179.04(13) ?
C4 C3 C5 C4 3_766 . . . -0.3(2) ?
O1 C4 C5 C6 . . . . 0.1(2) ?
C3 C4 C5 C6 3_766 . . . 179.68(13) ?
O1 C4 C5 C3 . . . . -179.32(14) ?
C3 C4 C5 C3 3_766 . . . 0.3(2) ?
C3 C5 C6 C7 . . . . 0.0(2) ?
C4 C5 C6 C7 . . . . -179.37(13) ?
C2 C1 C7 C6 . . . . -0.8(2) ?
C5 C6 C7 C1 . . . . 0.5(2) ?

_shelx_res_file                  
;

TITL ZNZ7811_0m_a.res in P2(1)/c
    ZNZ7811_0m.res
    created by SHELXL-2018/3 at 17:28:11 on 27-May-2019
CELL 1.34139 6.0211 5.2723 15.6347 90.000 94.048 90.000
ZERR 2.00 0.0004 0.0004 0.0012 0.000 0.004 0.000
LATT 1
SYMM -x, y+1/2, -z+1/2
SFAC C H O
UNIT 28 16 8
OMIT 1 0 8
OMIT 2 2 5
OMIT 1 0 2
LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
TEMP -80.160
ACTA
L.S. 4
FMAP 2
size 0.2 0.2 0.2
PLAN -1 0 0.00
HTAB
BOND $H
CONF
WGHT    0.092200    0.115700
SWAT    0.123874    0.5374
FVAR       1.51902
O1    3    1.318764    0.144548    0.519511    11.00000    0.03169    0.03495 =
         0.03491    0.00472    0.00765    0.01227
O2    3    0.494911    0.689059    0.615062    11.00000    0.02880    0.03784 =
         0.03382    0.00353    0.01027    0.00849
AFIX 147
H2A   2    0.510970    0.788833    0.574068    11.00000   -1.50000
AFIX   0
C1    1    0.668795    0.347113    0.687862    11.00000    0.02675    0.03652 =
         0.02654    0.00032    0.00687   -0.00280
AFIX  43
H1    2    0.556419    0.351809    0.727537    11.00000   -1.20000
AFIX   0
C2    1    0.663229    0.521146    0.620435    11.00000    0.02332    0.02975 =
         0.02843   -0.00500    0.00256   -0.00013
C3    1    0.829860    0.512501    0.561204    11.00000    0.02287    0.02690 =
         0.02420   -0.00234    0.00207    0.00002
C4    1    1.174011    0.308827    0.510159    11.00000    0.02334    0.02506 =
         0.02697   -0.00292    0.00064    0.00163
C5    1    0.997318    0.326454    0.572183    11.00000    0.02356    0.02560 =
         0.02364   -0.00184    0.00100   -0.00091
C6    1    1.000930    0.156261    0.639360    11.00000    0.02629    0.02873 =
         0.02970    0.00090    0.00096    0.00217
AFIX  43
H3    2    1.114825    0.031694    0.646089    11.00000   -1.20000
AFIX   0
C7    1    0.835087    0.169439    0.697314    11.00000    0.03240    0.03330 =
         0.02769    0.00432    0.00341   -0.00316
AFIX  43
H2    2    0.837503    0.053697    0.743939    11.00000   -1.20000

AFIX   0
HKLF 4 1 1 0 0 0 1 0 0 0 1




REM  ZNZ7811_0m_a.res in P2(1)/c
REM wR2 = 0.136103, GooF = S = 1.05015, Restrained GooF = 1.05015 for all data
REM R1 = 0.040806 for 761 Fo > 4sig(Fo) and 0.046528 for all 870 data
REM 85 parameters refined using 0 restraints

END

WGHT      0.0736      0.1534

REM Instructions for potential hydrogen bonds
EQIV $2 x-1, y+1, z
HTAB O2 O1_$2
EQIV $1 -x+2, -y+1, -z+1
HTAB O2 O1_$1
EQIV $3 -x+1, y-1/2, -z+3/2
HTAB C1 O2_$3

REM Highest difference peak  0.209,  deepest hole -0.243,  1-sigma level  0.051
Q1    1   1.0780  0.3329  0.5432  11.00000  0.05    0.21
;
_shelx_res_checksum              3510
