# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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#######################################################################

data_exp_26199_sqd
_database_code_depnum_ccdc_archive 'CCDC 2035078'
loop_
_audit_author_name
_audit_author_address
'Tian-Fu Liu'
;College of Chemistry and Materials Science, Fujian Normal University,
China
;
_audit_update_record             
;
2020-10-02 deposited with the CCDC.	2021-02-01 downloaded from the CCDC.
;
_audit_creation_date             2020-08-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H15 N7 O6'
_chemical_formula_sum            'C27 H12 N7 O6'
_chemical_formula_weight         530.44
_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'
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'

_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                   7.5193(4)
_cell_length_b                   19.0692(9)
_cell_length_c                   20.4491(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.627(4)
_cell_angle_gamma                90
_cell_volume                     2890.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2435
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      71.7590
_cell_measurement_theta_min      4.6090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1084
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11613
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.040
_diffrn_reflns_theta_min         4.386
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3361
_reflns_number_total             5643
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.344
_refine_diff_density_min         -0.756
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         5643
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1442
_refine_ls_R_factor_gt           0.1032
_refine_ls_restrained_S_all      1.137
_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)+(0.1440P)²+4.1679P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3024
_refine_ls_wR_factor_ref         0.3276
_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. Uiso/Uaniso restraints and constraints
Uanis(O00U) = Uanis(O00B) = Uanis(C014)
Uanis(O00L) = Uanis(C013) = Uanis(O012)
Uanis(O002) = Uanis(C010) = Uanis(O001)
3.a Aromatic/amide H refined with riding coordinates:
 C00I(H00I), C00M(H00M), C00N(H00N), C00O(H00O), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00T(H00T), C00V(H00V), C00W(H00W), C00Y(H00Y), C011(H011)
3.b Idealised tetrahedral OH refined as rotating group:
 O001(H001), O00B(H00B), O012(H012)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O001 O 1.0144(4) 0.32424(16) 0.90829(14) 0.0352(5) Uani 1 1 d . . . . .
H001 H 1.068762 0.330813 0.946014 0.053 Uiso 1 1 calc GR . . . .
O002 O 1.0043(4) 0.44144(16) 0.90868(14) 0.0352(5) Uani 1 1 d . . . . .
N003 N 0.2831(4) 0.37818(16) 0.51312(14) 0.0217(7) Uani 1 1 d . . . . .
N004 N 0.2886(4) 0.50174(15) 0.51186(14) 0.0224(7) Uani 1 1 d . . . . .
N005 N 0.4628(4) 0.44192(16) 0.59812(14) 0.0227(7) Uani 1 1 d . . . . .
N006 N 0.4614(4) 0.31564(16) 0.59986(14) 0.0219(7) Uani 1 1 d . . . . .
N007 N 0.2811(4) 0.25458(16) 0.51576(14) 0.0229(7) Uani 1 1 d . . . . .
N008 N 0.1016(4) 0.43841(16) 0.42617(15) 0.0235(7) Uani 1 1 d . . . . .
N009 N 0.0945(4) 0.31682(16) 0.42862(15) 0.0253(7) Uani 1 1 d . . . . .
C00A C 0.3468(4) 0.44172(19) 0.54098(17) 0.0207(7) Uani 1 1 d . . . . .
O00B O -0.2445(6) 0.0009(2) 0.2926(2) 0.0638(8) Uani 1 1 d . . . . .
H00B H -0.275873 -0.039094 0.281364 0.096 Uiso 1 1 calc GR . . . .
C00C C 0.3435(5) 0.31492(19) 0.54284(17) 0.0226(8) Uani 1 1 d . . . . .
C00D C 0.5116(5) 0.37904(19) 0.62504(17) 0.0212(7) Uani 1 1 d . . . . .
C00E C 0.1583(5) 0.37787(19) 0.45416(17) 0.0216(7) Uani 1 1 d . . . . .
C00F C 0.1681(5) 0.49711(19) 0.45558(17) 0.0226(8) Uani 1 1 d . . . . .
C00G C 0.6299(5) 0.3798(2) 0.69034(18) 0.0245(8) Uani 1 1 d . . . . .
C00H C 0.1556(5) 0.25855(19) 0.45997(17) 0.0229(8) Uani 1 1 d . . . . .
C00I C 0.1592(5) 0.6280(2) 0.4532(2) 0.0284(8) Uani 1 1 d . . . . .
H00I H 0.245400 0.628921 0.491508 0.034 Uiso 1 1 calc R . . . .
C00J C 0.0977(5) 0.56393(19) 0.42512(18) 0.0242(8) Uani 1 1 d . . . . .
C00K C 0.0771(5) 0.1918(2) 0.43278(18) 0.0252(8) Uani 1 1 d . . . . .
O00L O -0.2343(6) 0.7531(2) 0.2846(2) 0.0654(8) Uani 1 1 d . . . . .
C00M C -0.0323(5) 0.5626(2) 0.36748(18) 0.0250(8) Uani 1 1 d . . . . .
H00M H -0.072640 0.519916 0.348494 0.030 Uiso 1 1 calc R . . . .
C00N C 0.6934(5) 0.3172(2) 0.72097(18) 0.0252(8) Uani 1 1 d . . . . .
H00N H 0.661402 0.274686 0.699919 0.030 Uiso 1 1 calc R . . . .
C00O C 0.6794(5) 0.4436(2) 0.72151(19) 0.0269(8) Uani 1 1 d . . . . .
H00O H 0.638167 0.485478 0.701147 0.032 Uiso 1 1 calc R . . . .
C00P C 0.8517(5) 0.3813(2) 0.81405(18) 0.0265(8) Uani 1 1 d . . . . .
C00Q C -0.1012(5) 0.6254(2) 0.33855(19) 0.0300(9) Uani 1 1 d . . . . .
H00Q H -0.188822 0.624632 0.300627 0.036 Uiso 1 1 calc R . . . .
C00R C 0.0919(5) 0.6904(2) 0.4239(2) 0.0292(9) Uani 1 1 d . . . . .
H00R H 0.133506 0.733091 0.442348 0.035 Uiso 1 1 calc R . . . .
C00S C -0.0478(6) 0.1924(2) 0.37369(19) 0.0309(9) Uani 1 1 d . . . . .
H00S H -0.082207 0.234529 0.352431 0.037 Uiso 1 1 calc R . . . .
C00T C 0.8044(5) 0.3177(2) 0.78297(19) 0.0280(8) Uani 1 1 d . . . . .
H00T H 0.846296 0.275839 0.803225 0.034 Uiso 1 1 calc R . . . .
O00U O -0.0988(6) -0.0561(2) 0.3816(2) 0.0638(8) Uani 1 1 d . . . . .
C00V C 0.1275(6) 0.1280(2) 0.4639(2) 0.0301(9) Uani 1 1 d . . . . .
H00V H 0.210785 0.127533 0.502991 0.036 Uiso 1 1 calc R . . . .
C00W C 0.7909(5) 0.4443(2) 0.78340(18) 0.0281(8) Uani 1 1 d . . . . .
H00W H 0.824668 0.486787 0.804205 0.034 Uiso 1 1 calc R . . . .
C00X C -0.0387(5) 0.6888(2) 0.3665(2) 0.0311(9) Uani 1 1 d . . . . .
C00Y C -0.1196(6) 0.1295(2) 0.3472(2) 0.0338(9) Uani 1 1 d . . . . .
H00Y H -0.203274 0.129835 0.308124 0.041 Uiso 1 1 calc R . . . .
C00Z C -0.0684(6) 0.0663(2) 0.3781(2) 0.0340(9) Uani 1 1 d . . . . .
C010 C 0.9652(6) 0.3825(2) 0.8818(2) 0.0352(5) Uani 1 1 d . . . . .
C011 C 0.0558(6) 0.0660(2) 0.4375(2) 0.0365(10) Uani 1 1 d . . . . .
H011 H 0.089331 0.023924 0.459031 0.044 Uiso 1 1 calc R . . . .
O012 O -0.0573(6) 0.8114(2) 0.3655(2) 0.0654(8) Uani 1 1 d . . . . .
H012 H -0.117557 0.844518 0.348464 0.098 Uiso 1 1 calc GR . . . .
C013 C -0.1127(9) 0.7560(3) 0.3366(3) 0.0654(8) Uani 1 1 d . . . . .
C014 C -0.1426(9) -0.0007(3) 0.3485(3) 0.0638(8) 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
O001 H001 0.8200 . ?
O001 C010 1.264(5) . ?
O002 C010 1.264(5) . ?
N003 C00A 1.390(4) . ?
N003 C00C 1.392(4) . ?
N003 C00E 1.398(4) . ?
N004 C00A 1.330(4) . ?
N004 C00F 1.343(5) . ?
N005 C00A 1.336(5) . ?
N005 C00D 1.345(5) . ?
N006 C00C 1.342(5) . ?
N006 C00D 1.343(5) . ?
N007 C00C 1.328(5) . ?
N007 C00H 1.356(5) . ?
N008 C00E 1.327(5) . ?
N008 C00F 1.328(5) . ?
N009 C00E 1.332(5) . ?
N009 C00H 1.326(5) . ?
O00B H00B 0.8200 . ?
O00B C014 1.265(7) . ?
C00D C00G 1.476(5) . ?
C00F C00J 1.477(5) . ?
C00G C00N 1.395(5) . ?
C00G C00O 1.394(5) . ?
C00H C00K 1.473(5) . ?
C00I H00I 0.9300 . ?
C00I C00J 1.395(5) . ?
C00I C00R 1.389(5) . ?
C00J C00M 1.400(5) . ?
C00K C00S 1.401(6) . ?
C00K C00V 1.394(5) . ?
O00L C013 1.283(8) . ?
C00M H00M 0.9300 . ?
C00M C00Q 1.397(5) . ?
C00N H00N 0.9300 . ?
C00N C00T 1.397(5) . ?
C00O H00O 0.9300 . ?
C00O C00W 1.397(5) . ?
C00P C00T 1.387(6) . ?
C00P C00W 1.397(5) . ?
C00P C010 1.500(5) . ?
C00Q H00Q 0.9300 . ?
C00Q C00X 1.386(6) . ?
C00R H00R 0.9300 . ?
C00R C00X 1.399(6) . ?
C00S H00S 0.9300 . ?
C00S C00Y 1.387(5) . ?
C00T H00T 0.9300 . ?
O00U C014 1.269(7) . ?
C00V H00V 0.9300 . ?
C00V C011 1.371(5) . ?
C00W H00W 0.9300 . ?
C00X C013 1.486(7) . ?
C00Y H00Y 0.9300 . ?
C00Y C00Z 1.386(6) . ?
C00Z C011 1.403(6) . ?
C00Z C014 1.482(6) . ?
C011 H011 0.9300 . ?
O012 H012 0.8200 . ?
O012 C013 1.248(8) . ?

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
C010 O001 H001 109.5 . . ?
C00A N003 C00C 120.8(3) . . ?
C00A N003 C00E 119.5(3) . . ?
C00C N003 C00E 119.7(3) . . ?
C00A N004 C00F 116.8(3) . . ?
C00A N005 C00D 116.7(3) . . ?
C00C N006 C00D 116.4(3) . . ?
C00C N007 C00H 116.8(3) . . ?
C00F N008 C00E 117.9(3) . . ?
C00H N009 C00E 118.0(3) . . ?
N004 C00A N003 120.1(3) . . ?
N004 C00A N005 120.5(3) . . ?
N005 C00A N003 119.4(3) . . ?
C014 O00B H00B 109.5 . . ?
N006 C00C N003 119.4(3) . . ?
N007 C00C N003 120.1(3) . . ?
N007 C00C N006 120.5(3) . . ?
N005 C00D C00G 116.3(3) . . ?
N006 C00D N005 127.3(3) . . ?
N006 C00D C00G 116.4(3) . . ?
N008 C00E N003 119.3(3) . . ?
N008 C00E N009 121.5(3) . . ?
N009 C00E N003 119.2(3) . . ?
N004 C00F C00J 116.6(3) . . ?
N008 C00F N004 126.3(3) . . ?
N008 C00F C00J 117.1(3) . . ?
C00N C00G C00D 120.5(3) . . ?
C00O C00G C00D 119.8(3) . . ?
C00O C00G C00N 119.8(3) . . ?
N007 C00H C00K 116.6(3) . . ?
N009 C00H N007 126.1(3) . . ?
N009 C00H C00K 117.2(3) . . ?
C00J C00I H00I 120.0 . . ?
C00R C00I H00I 120.0 . . ?
C00R C00I C00J 120.0(4) . . ?
C00I C00J C00F 120.7(3) . . ?
C00I C00J C00M 119.9(3) . . ?
C00M C00J C00F 119.3(3) . . ?
C00S C00K C00H 119.1(3) . . ?
C00V C00K C00H 121.4(3) . . ?
C00V C00K C00S 119.5(4) . . ?
C00J C00M H00M 120.1 . . ?
C00Q C00M C00J 119.9(4) . . ?
C00Q C00M H00M 120.1 . . ?
C00G C00N H00N 119.7 . . ?
C00G C00N C00T 120.6(4) . . ?
C00T C00N H00N 119.7 . . ?
C00G C00O H00O 120.1 . . ?
C00G C00O C00W 119.8(4) . . ?
C00W C00O H00O 120.1 . . ?
C00T C00P C00W 120.4(3) . . ?
C00T C00P C010 120.0(4) . . ?
C00W C00P C010 119.6(4) . . ?
C00M C00Q H00Q 120.1 . . ?
C00X C00Q C00M 119.9(3) . . ?
C00X C00Q H00Q 120.1 . . ?
C00I C00R H00R 120.1 . . ?
C00I C00R C00X 119.9(4) . . ?
C00X C00R H00R 120.1 . . ?
C00K C00S H00S 120.3 . . ?
C00Y C00S C00K 119.4(4) . . ?
C00Y C00S H00S 120.3 . . ?
C00N C00T H00T 120.3 . . ?
C00P C00T C00N 119.4(4) . . ?
C00P C00T H00T 120.3 . . ?
C00K C00V H00V 119.6 . . ?
C011 C00V C00K 120.9(4) . . ?
C011 C00V H00V 119.6 . . ?
C00O C00W H00W 120.0 . . ?
C00P C00W C00O 120.0(4) . . ?
C00P C00W H00W 120.0 . . ?
C00Q C00X C00R 120.4(4) . . ?
C00Q C00X C013 120.4(4) . . ?
C00R C00X C013 119.2(5) . . ?
C00S C00Y H00Y 119.6 . . ?
C00Z C00Y C00S 120.8(4) . . ?
C00Z C00Y H00Y 119.6 . . ?
C00Y C00Z C011 119.5(4) . . ?
C00Y C00Z C014 120.4(4) . . ?
C011 C00Z C014 120.1(5) . . ?
O001 C010 O002 124.4(4) . . ?
O001 C010 C00P 117.6(4) . . ?
O002 C010 C00P 118.1(4) . . ?
C00V C011 C00Z 119.9(4) . . ?
C00V C011 H011 120.1 . . ?
C00Z C011 H011 120.1 . . ?
C013 O012 H012 109.5 . . ?
O00L C013 C00X 118.0(6) . . ?
O012 C013 O00L 124.4(5) . . ?
O012 C013 C00X 117.6(6) . . ?
O00B C014 O00U 124.4(5) . . ?
O00B C014 C00Z 118.6(5) . . ?
O00U C014 C00Z 117.0(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# SQUEEZE RESULTS (Version =  21116)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.175 0.127 0.730 191 50 ' '
2 0.142 0.373 0.230 191 50 ' '
3 -0.080 0.627 0.770 192 50 ' '
4 0.154 0.873 0.270 192 50 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?
