# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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. 
# 
#######################################################################

data_w_sq
_database_code_depnum_ccdc_archive 'CCDC 2003702'
loop_
_audit_author_name
_audit_author_address
'yan yang tian'
;Xian Polytechnic University
China
;
_audit_update_record             
;
2020-05-13 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;
_audit_creation_date             2017-06-14
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.13(C184 H112 Cu16 O96)'
_chemical_formula_sum            'C23 H14 Cu2 O12'
_chemical_formula_weight         609.42
_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 0.0033 0.0016 '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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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      tetragonal
_space_group_IT_number           141
_space_group_name_H-M_alt        'I 41/a m d'
_space_group_name_Hall           '-I 4bd 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+1/4, x+3/4, z+1/4'
'y+1/4, -x+1/4, z+3/4'
'-x+1/2, y, -z+1/2'
'x, -y, -z'
'y+1/4, x+3/4, -z+1/4'
'-y+1/4, -x+1/4, -z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+3/4, x+5/4, z+3/4'
'y+3/4, -x+3/4, z+5/4'
'-x+1, y+1/2, -z+1'
'x+1/2, -y+1/2, -z+1/2'
'y+3/4, x+5/4, -z+3/4'
'-y+3/4, -x+3/4, -z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-1/4, -x-3/4, -z-1/4'
'-y-1/4, x-1/4, -z-3/4'
'x-1/2, -y, z-1/2'
'-x, y, z'
'-y-1/4, -x-3/4, z-1/4'
'y-1/4, x-1/4, z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y+1/4, -x-1/4, -z+1/4'
'-y+1/4, x+1/4, -z-1/4'
'x, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
'-y+1/4, -x-1/4, z+1/4'
'y+1/4, x+1/4, z-1/4'

_cell_length_a                   28.727(2)
_cell_length_b                   28.727(2)
_cell_length_c                   14.5895(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     12040(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4166
_cell_measurement_temperature    293
_cell_measurement_theta_max      24.834
_cell_measurement_theta_min      2.545
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.672
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2448
_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  0.0968
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            30342
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.678
_diffrn_reflns_theta_max         25.678
_diffrn_reflns_theta_min         1.418
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1827
_reflns_number_total             2987
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.18C (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.18C (?, 2016)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.859
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.133
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         2987
_refine_ls_number_restraints     145
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0737
_refine_ls_restrained_S_all      1.106
_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)+(0.1656P)²+10.3168P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2280
_refine_ls_wR_factor_ref         0.2673
_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, All O(H,H) groups
2. Restrained distances
 C11-C8
 1.4 with sigma of 0.02
 O4-C11
 1.2 with sigma of 0.02
 C11-C9
 2.5 with sigma of 0.02
 C11-O3
 1.2 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C9) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C7) \\sim
Ueq, Uanis(C10) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of
0.02
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: O3(0.25) H3(0.25) O4(0.25) C5(0.5) C3(0.5) H3A(0.5) C4(0.5)
 H4(0.5) C8(0.5) H8(0.25) C9(0.25) H9(0.25) C10(0.25) H10(0.25) C11(0.25)
 C6(0.5) H6(0.5) C7(0.5)
6.a Riding coordinates:
 O3(H3), O5(H5A,H5B), C4(H4), C6(H6)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C8(H8), C9(H9), C10(H10)
;
_atom_sites_solution_hydrogens   mixed
_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
Cu1 Cu 0.27136(2) 0.750000 0.16966(7) 0.0530(4) Uani 1 2 d S TU P . .
O3 O 0.3150(10) 0.8605(10) 0.621(3) 0.215(17) Uani 0.25 1 d D U . A 1
H3 H 0.314936 0.884289 0.654360 0.323 Uiso 0.25 1 d R . . A 1
O2 O 0.27454(11) 0.79799(11) 0.3609(3) 0.0622(11) Uani 1 1 d . U . . .
O1 O 0.31164(11) 0.79733(11) 0.2255(3) 0.0650(11) Uani 1 1 d . U . . .
O4 O 0.3718(12) 0.8341(9) 0.701(2) 0.170(12) Uani 0.25 1 d D U . A 1
O5 O 0.3042(3) 0.750000 0.0376(5) 0.108(2) Uani 1 2 d S TU P . .
H5A H 0.333423 0.750000 0.028238 0.162 Uiso 1 2 d RS T P . .
H5B H 0.289973 0.750000 -0.013502 0.162 Uiso 1 2 d RS T P . .
C5 C 0.3645(3) 0.8365(3) 0.4215(8) 0.058(3) Uani 0.5 1 d . U . B -1
C3 C 0.3550(5) 0.8825(4) 0.2888(10) 0.083(4) Uani 0.5 1 d . U . B -1
H3A H 0.344122 0.884735 0.228924 0.100 Uiso 0.5 1 calc R . . B -1
C4 C 0.3836(4) 0.9157(3) 0.3216(9) 0.068(3) Uani 0.5 1 d . U . B -1
H4 H 0.388777 0.942697 0.287974 0.081 Uiso 0.5 1 d R . . B -1
C8 C 0.3550(5) 0.7910(5) 0.5745(10) 0.092(4) Uani 0.5 1 d D U . . .
H8 H 0.357300 0.817740 0.610023 0.110 Uiso 0.25 1 calc R . . C 2
C9 C 0.3467(9) 0.750000 0.6095(18) 0.118(6) Uani 0.5 2 d DS TU P . .
H9 H 0.333070 0.750000 0.667305 0.142 Uiso 0.5 2 calc RS T P . .
C1 C 0.30578(18) 0.81060(16) 0.3077(5) 0.0601(14) Uani 1 1 d . U . . .
C2 C 0.34130(18) 0.84418(17) 0.3433(5) 0.0639(16) Uani 1 1 d . U . . .
C10 C 0.3661(4) 0.750000 0.4316(10) 0.047(3) Uani 0.5 2 d S TU P . .
H10 H 0.374288 0.749999 0.369960 0.057 Uiso 0.5 2 calc RS T P A .
C11 C 0.3459(11) 0.8322(6) 0.636(2) 0.120(8) Uani 0.25 1 d D U . A 1
C6 C 0.3965(3) 0.8701(3) 0.4560(9) 0.057(3) Uani 0.5 1 d . U . B -1
H6 H 0.410529 0.865388 0.512652 0.068 Uiso 0.5 1 d R . . B -1
C7 C 0.3601(3) 0.7914(3) 0.4764(8) 0.061(2) Uani 0.5 1 d . U . B .


_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
Cu1 Cu1 2.646(2) 25_565 ?
Cu1 O2 1.959(3) 5 ?
Cu1 O2 1.959(3) 25_565 ?
Cu1 O1 1.962(3) . ?
Cu1 O1 1.962(3) 29_565 ?
Cu1 O5 2.146(8) . ?
O3 H3 0.8347 . ?
O3 C11 1.223(18) . ?
O2 C1 1.241(7) . ?
O1 C1 1.269(8) . ?
O4 C11 1.203(18) . ?
O5 H5A 0.8501 . ?
O5 H5B 0.8503 . ?
C5 C2 1.341(12) . ?
C5 C6 1.424(13) . ?
C5 C7 1.528(14) . ?
C3 H3A 0.9300 . ?
C3 C4 1.346(15) . ?
C3 C2 1.413(14) . ?
C4 H4 0.9301 . ?
C4 C2 1.411(13) 8_665 ?
C8 H8 0.9300 . ?
C8 C9 1.305(16) . ?
C8 C11 1.507(16) . ?
C8 C7 1.438(17) . ?
C9 H9 0.9300 . ?
C1 C2 1.497(7) . ?
C2 C6 1.349(12) 8_665 ?
C10 H10 0.9300 . ?
C10 C7 1.368(13) . ?
C10 C7 1.368(12) 29_565 ?
C6 H6 0.9292 . ?

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
O2 Cu1 Cu1 83.66(14) 5 25_565 ?
O2 Cu1 Cu1 83.66(14) 25_565 25_565 ?
O2 Cu1 O2 89.44(18) 25_565 5 ?
O2 Cu1 O1 90.21(14) 25_565 29_565 ?
O2 Cu1 O1 90.21(14) 5 . ?
O2 Cu1 O1 168.22(18) 25_565 . ?
O2 Cu1 O1 168.22(18) 5 29_565 ?
O2 Cu1 O5 95.3(2) 5 . ?
O2 Cu1 O5 95.3(2) 25_565 . ?
O1 Cu1 Cu1 84.60(14) 29_565 25_565 ?
O1 Cu1 Cu1 84.60(14) . 25_565 ?
O1 Cu1 O1 87.7(2) . 29_565 ?
O1 Cu1 O5 96.5(2) . . ?
O1 Cu1 O5 96.5(2) 29_565 . ?
O5 Cu1 Cu1 178.5(2) . 25_565 ?
C11 O3 H3 116.5 . . ?
C1 O2 Cu1 123.3(4) . 25_565 ?
C1 O1 Cu1 121.5(4) . . ?
Cu1 O5 H5A 125.3 . . ?
Cu1 O5 H5B 125.1 . . ?
H5A O5 H5B 109.5 . . ?
C2 C5 C6 120.7(9) . . ?
C2 C5 C7 123.0(8) . . ?
C6 C5 C7 116.3(9) . . ?
C4 C3 H3A 119.3 . . ?
C4 C3 C2 121.4(12) . . ?
C2 C3 H3A 119.3 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C2 119.2(10) . 8_665 ?
C2 C4 H4 120.6 8_665 . ?
C9 C8 H8 122.7 . . ?
C9 C8 C11 116.5(17) . . ?
C9 C8 C7 114.6(16) . . ?
C7 C8 H8 122.7 . . ?
C7 C8 C11 127.0(17) . . ?
C8 C9 C8 129(2) 29_565 . ?
C8 C9 H9 115.6 . . ?
C8 C9 H9 115.6 29_565 . ?
O2 C1 O1 126.8(5) . . ?
O2 C1 C2 117.6(6) . . ?
O1 C1 C2 115.5(6) . . ?
C5 C2 C3 117.9(7) . . ?
C5 C2 C1 121.9(6) . . ?
C5 C2 C6 94.4(7) . 8_665 ?
C3 C2 C1 119.7(7) . . ?
C6 C2 C3 46.8(7) 8_665 . ?
C6 C2 C1 120.2(7) 8_665 . ?
C7 C10 H10 119.6 . . ?
C7 C10 H10 119.6 29_565 . ?
C7 C10 C7 120.8(15) 29_565 . ?
O3 C11 C8 123(3) . . ?
O4 C11 O3 124(3) . . ?
O4 C11 C8 113(2) . . ?
C5 C6 H6 119.7 . . ?
C8 C7 C5 122.5(10) . . ?
C10 C7 C5 118.4(11) . . ?
C10 C7 C8 118.8(11) . . ?

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
Cu1 O2 C1 O1 4.5(7) 25_565 . . . ?
Cu1 O2 C1 C2 -174.1(3) 25_565 . . . ?
Cu1 O1 C1 O2 -3.0(7) . . . . ?
Cu1 O1 C1 C2 175.5(3) . . . . ?
O2 C1 C2 C5 51.7(9) . . . . ?
O2 C1 C2 C3 -135.8(9) . . . . ?
O2 C1 C2 C6 169.6(6) . . . 8_665 ?
O1 C1 C2 C5 -127.0(8) . . . . ?
O1 C1 C2 C3 45.5(10) . . . . ?
O1 C1 C2 C6 -9.1(8) . . . 8_665 ?
C4 C3 C2 C5 -13.4(18) . . . . ?
C4 C3 C2 C1 173.8(11) . . . . ?
C4 C3 C2 C6 -81.2(14) . . . 8_665 ?
C9 C8 C11 O3 -113(4) . . . . ?
C9 C8 C11 O4 66(4) . . . . ?
C9 C8 C7 C5 173.1(16) . . . . ?
C9 C8 C7 C10 -14(2) . . . . ?
C2 C5 C7 C8 -135.4(12) . . . . ?
C2 C5 C7 C10 51.4(14) . . . . ?
C2 C3 C4 C2 10(2) . . . 8_665 ?
C11 C8 C9 C8 -174(2) . . . 29_565 ?
C11 C8 C7 C5 10(3) . . . . ?
C11 C8 C7 C10 -177.0(19) . . . . ?
C6 C5 C2 C3 10.5(14) . . . . ?
C6 C5 C2 C1 -176.9(8) . . . . ?
C6 C5 C2 C6 53.1(10) . . . 8_665 ?
C6 C5 C7 C8 46.8(15) . . . . ?
C6 C5 C7 C10 -126.3(11) . . . . ?
C7 C5 C2 C3 -167.2(11) . . . . ?
C7 C5 C2 C1 5.4(14) . . . . ?
C7 C5 C2 C6 -124.6(10) . . . 8_665 ?
C7 C8 C9 C8 21(4) . . . 29_565 ?
C7 C8 C11 O3 50(5) . . . . ?
C7 C8 C11 O4 -131(3) . . . . ?
C7 C10 C7 C5 -176.6(7) 29_565 . . . ?
C7 C10 C7 C8 10.0(19) 29_565 . . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
