# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_20201225-dw1_sq
_database_code_depnum_ccdc_archive 'CCDC 2164832'
loop_
_audit_author_name
_audit_author_address
'wen dai'
;Xiamen University
China
;
_audit_update_record             
;
2023-08-25 deposited with the CCDC.	2023-12-21 downloaded from the CCDC.
;
_audit_creation_date             2023-08-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.17(C120 H72 Cu6 N24 O42), 2(O)'
_chemical_formula_sum            'C20 H18 Cu N4 O9'
_chemical_formula_weight         521.92
_chemical_absolute_configuration ?
_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'
Cu Cu -1.9646 0.5888 '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      hexagonal
_space_group_IT_number           179
_space_group_name_H-M_alt        'P 65 2 2'
_space_group_name_Hall           'P 65 2 (0 0 1)'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'
'y, -x+y, z+1/6'
'x-y, x, z+5/6'
'y, x, -z+2/3'
'x-y, -y, -z'
'-x, -x+y, -z+1/3'
'-y, -x, -z+1/6'
'-x+y, y, -z+1/2'
'x, x-y, -z+5/6'

_cell_length_a                   18.8181(8)
_cell_length_b                   18.8181(8)
_cell_length_c                   23.6351(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7248.4(7)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    6960
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.3430
_cell_measurement_theta_min      4.6100
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.886
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    0.717
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1602
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            18325
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.733
_diffrn_reflns_theta_min         3.294
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5148
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -32.00  -2.00   1.00   20.23    --  -40.45 125.00 -60.00   30
  2  ω    -65.00  29.00   1.00   20.23    --  -40.45  38.00-120.00   94
  3  ω    132.00 172.00   1.00   20.23    --  103.24 125.00   0.00   40
  4  ω    109.00 165.00   1.00   20.23    --  103.24 112.00-107.00   56
  5  ω     75.00 175.00   1.00   20.23    --  103.24  61.00-180.00  100
  6  ω    142.00 173.00   1.00   20.23    --  103.24 126.00 -97.00   31
  7  ω    127.00 155.00   1.00   20.23    --  103.24  45.00 150.00   28
  8  ω     94.00 129.00   1.00   20.23    --  103.24 125.00   0.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0712045000
_diffrn_orient_matrix_UB_12      -0.0122527000
_diffrn_orient_matrix_UB_13      -0.0197531000
_diffrn_orient_matrix_UB_21      0.0620133000
_diffrn_orient_matrix_UB_22      0.0889134000
_diffrn_orient_matrix_UB_23      0.0169861000
_diffrn_orient_matrix_UB_31      0.0058988000
_diffrn_orient_matrix_UB_32      -0.0292946000
_diffrn_orient_matrix_UB_33      0.0597830000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3860
_reflns_number_total             4728
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.14(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         4728
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0527
_refine_ls_restrained_S_all      1.065
_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)+(0.0984P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1527
_refine_special_details          
'Refined as a 2-component inversion twin.,SQUEEZE'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.86(6)
 0.14(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
3. Uiso/Uaniso restraints and constraints
C8 \\sim C3 \\sim C6 \\sim C9 \\sim C7 \\sim C11 \\sim C2 \\sim C10 \\sim C4
\\sim C5 \\sim C1: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
Uanis(O1) = Uanis(O2) = Uanis(O3)
Uanis(N1) = Uanis(N2)
4.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C2(H2), C10(H10), C4(H4), C5(H5), C1(H1A)
;
_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
Cu1 Cu 1.21881(3) 0.78119(3) 0.5833 0.0450(3) Uani 1 2 d S T P . .
O2 O 0.8560(2) 0.5567(2) 0.80654(12) 0.0618(5) Uani 1 1 d . . . . .
O4 O 1.14645(16) 0.85355(16) 0.5833 0.0701(13) Uani 1 2 d S T P . .
O3 O 1.0393(2) 0.6595(2) 0.85011(12) 0.0618(5) Uani 1 1 d . . . . .
N2 N 1.1495(2) 0.7088(2) 0.64586(12) 0.0478(6) Uani 1 1 d . . . . .
O1 O 0.7573(2) 0.4268(2) 0.81511(11) 0.0618(5) Uani 1 1 d . . . . .
N1 N 1.0209(2) 0.5620(2) 0.78409(12) 0.0478(6) Uani 1 1 d . . . . .
H1 H 0.9991 0.5089 0.7785 0.057 Uiso 1 1 calc R . . . .
C8 C 0.9584(2) 0.5187(3) 0.87603(13) 0.0457(9) Uani 1 1 d . U . . .
C3 C 1.0652(3) 0.6136(3) 0.73893(14) 0.0486(10) Uani 1 1 d . U . . .
C6 C 1.0082(3) 0.5857(3) 0.83549(16) 0.0512(10) Uani 1 1 d . U . . .
C9 C 0.8733(2) 0.4741(3) 0.87461(14) 0.0461(9) Uani 1 1 d . U . . .
C7 C 1.0012(3) 0.50059(17) 0.9167 0.0529(15) Uani 1 2 d S TU P . .
H7 H 1.0595 0.5297 0.9167 0.063 Uiso 1 2 calc RS T P . .
C11 C 0.8258(3) 0.4879(3) 0.82945(17) 0.0517(10) Uani 1 1 d . U . . .
C2 C 1.0826(3) 0.6947(4) 0.73471(17) 0.0640(13) Uani 1 1 d . U . . .
H2 H 1.0673 0.7192 0.7639 0.077 Uiso 1 1 calc R . . . .
C10 C 0.8318(3) 0.41591(16) 0.9167 0.0450(12) Uani 1 2 d S TU P . .
H10 H 0.7735 0.3868 0.9167 0.054 Uiso 1 2 calc RS T P . .
C4 C 1.0926(3) 0.5828(3) 0.69643(15) 0.0510(10) Uani 1 1 d . U . . .
H4 H 1.0834 0.5285 0.6988 0.061 Uiso 1 1 calc R . . . .
C5 C 1.1332(3) 0.6315(3) 0.65052(16) 0.0476(9) Uani 1 1 d . U . . .
H5 H 1.1504 0.6091 0.6211 0.057 Uiso 1 1 calc R . . . .
C1 C 1.1231(4) 0.7386(3) 0.68642(19) 0.0704(14) Uani 1 1 d . U . . .
H1A H 1.1323 0.7928 0.6823 0.085 Uiso 1 1 calc R . . . .
O01 O 0.9473(4) 0.3952(4) 0.7624(3) 0.1235(18) Uiso 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
Cu1 O2 1.982(3) 9_766 ?
Cu1 O2 1.982(3) 6_654 ?
Cu1 O4 2.359(5) . ?
Cu1 N2 1.991(3) 10_776 ?
Cu1 N2 1.991(3) . ?
O2 Cu1 1.982(3) 5_565 ?
O2 C11 1.247(6) . ?
O3 C6 1.257(6) . ?
N2 C5 1.333(6) . ?
N2 C1 1.326(6) . ?
O1 C11 1.272(5) . ?
N1 H1 0.8800 . ?
N1 C3 1.403(5) . ?
N1 C6 1.356(5) . ?
C8 C6 1.484(5) . ?
C8 C9 1.388(6) . ?
C8 C7 1.401(5) . ?
C3 C2 1.396(7) . ?
C3 C4 1.381(6) . ?
C9 C11 1.496(5) . ?
C9 C10 1.393(5) . ?
C7 C8 1.401(5) 12_556 ?
C7 H7 0.9500 . ?
C2 H2 0.9500 . ?
C2 C1 1.391(6) . ?
C10 C9 1.393(5) 12_556 ?
C10 H10 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.379(5) . ?
C5 H5 0.9500 . ?
C1 H1A 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
O2 Cu1 O2 174.6(2) 9_766 6_654 ?
O2 Cu1 O4 92.69(11) 6_654 . ?
O2 Cu1 O4 92.69(11) 9_766 . ?
O2 Cu1 N2 90.31(14) 9_766 . ?
O2 Cu1 N2 90.32(14) 6_654 10_776 ?
O2 Cu1 N2 89.55(13) 6_654 . ?
O2 Cu1 N2 89.55(13) 9_766 10_776 ?
N2 Cu1 O4 91.43(12) 10_776 . ?
N2 Cu1 O4 91.43(12) . . ?
N2 Cu1 N2 177.1(2) 10_776 . ?
C11 O2 Cu1 112.4(3) . 5_565 ?
C5 N2 Cu1 121.5(3) . . ?
C1 N2 Cu1 120.2(3) . . ?
C1 N2 C5 118.1(4) . . ?
C3 N1 H1 116.7 . . ?
C6 N1 H1 116.7 . . ?
C6 N1 C3 126.5(4) . . ?
C9 C8 C6 123.1(3) . . ?
C9 C8 C7 119.9(4) . . ?
C7 C8 C6 116.9(4) . . ?
C2 C3 N1 123.0(4) . . ?
C4 C3 N1 118.7(4) . . ?
C4 C3 C2 118.3(4) . . ?
O3 C6 N1 123.3(4) . . ?
O3 C6 C8 120.5(4) . . ?
N1 C6 C8 116.1(4) . . ?
C8 C9 C11 121.4(4) . . ?
C8 C9 C10 118.8(4) . . ?
C10 C9 C11 119.8(4) . . ?
C8 C7 C8 120.3(5) 12_556 . ?
C8 C7 H7 119.9 12_556 . ?
C8 C7 H7 119.9 . . ?
O2 C11 O1 123.5(4) . . ?
O2 C11 C9 119.3(4) . . ?
O1 C11 C9 117.2(4) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 C3 117.8(5) . . ?
C1 C2 H2 121.1 . . ?
C9 C10 C9 121.9(5) 12_556 . ?
C9 C10 H10 119.0 12_556 . ?
C9 C10 H10 119.0 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.6(4) . . ?
C5 C4 H4 120.2 . . ?
N2 C5 C4 122.5(4) . . ?
N2 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
N2 C1 C2 123.5(5) . . ?
N2 C1 H1A 118.2 . . ?
C2 C1 H1A 118.2 . . ?

_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 2.282
_oxdiff_exptl_absorpt_empirical_full_min 0.390
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.86(6)
2 0.14(6)

_exptl_crystal_recrystallization_method 'solvothermal reaction'
