# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_20170327d23_0m
_database_code_depnum_ccdc_archive 'CCDC 1916820'
loop_
_audit_author_name
_audit_author_address
'Jun Zhang'
;Anhui Jianzhu University
China
;
_audit_update_record             
;
2019-05-17 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;
_audit_creation_date             2019-05-16
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H12 Cu2 O16, 4(Cl), 7(H2 O)'
_chemical_formula_sum            'C20 H26 Cl4 Cu2 O23'
_chemical_formula_weight         903.31
_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 0.0030 0.0020 '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'
Cl Cl 0.1480 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3200 1.2650 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7389(11)
_cell_length_b                   10.6086(15)
_cell_length_c                   10.6178(15)
_cell_angle_alpha                112.829(2)
_cell_angle_beta                 90.455(2)
_cell_angle_gamma                104.055(2)
_cell_volume                     774.27(19)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1698
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.334
_cell_measurement_theta_min      2.731
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.817
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.937
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6047
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.098
_diffrn_reflns_theta_min         2.095
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 7.9
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2402
_reflns_number_total             3068
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.761
_refine_diff_density_min         -0.638
_refine_diff_density_rms         0.144
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3068
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0574
_refine_ls_restrained_S_all      1.064
_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)+(0.0881P)²+2.5507P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.1677
_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. Others
 Fixed Sof: O12(0.5) H12A(0.5) H12B(0.5)
3.a Riding coordinates:
 O5(H5), O2(H2), O4(H4), O8(H8), O9(H9A,H9B), O10(H10A,H10B), O11(H11A,H11B),
 O12(H12A,H12B)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5A), C10(H10)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.49709(9) 0.76597(7) 0.23510(6) 0.0196(2) Uani 1 1 d . . . . .
O5 O 0.4536(6) 0.7322(4) 1.0402(4) 0.0274(9) Uani 1 1 d . . . . .
H5 H 0.369020 0.698594 0.983268 0.041 Uiso 1 1 d R . . . .
O3 O 0.4464(5) 1.0276(4) 0.7251(4) 0.0270(9) Uani 1 1 d . . . . .
O7 O 0.5660(6) 0.4364(4) 0.8100(4) 0.0314(10) Uani 1 1 d . . . . .
O2 O 0.7981(6) 0.7275(5) 0.3962(4) 0.0358(11) Uani 1 1 d . . . . .
H2 H 0.758040 0.682641 0.314943 0.054 Uiso 1 1 d R . . . .
O4 O 0.7338(6) 1.0831(4) 0.6952(5) 0.0346(10) Uani 1 1 d . . . . .
H4 H 0.767527 1.168628 0.687529 0.7(4) Uiso 1 1 d R . . . .
O1 O 0.5512(6) 0.8059(4) 0.4278(4) 0.0297(10) Uani 1 1 d . . . . .
O6 O 0.7332(6) 0.7269(5) 1.0593(4) 0.0356(10) Uani 1 1 d . . . . .
O8 O 0.8128(6) 0.4398(5) 0.7020(5) 0.0373(11) Uani 1 1 d . . . . .
H8 H 0.906260 0.502941 0.719687 0.056 Uiso 1 1 d R . . . .
C1 C 0.6763(8) 0.7647(5) 0.4645(6) 0.0216(12) Uani 1 1 d . . . . .
C7 C 0.6009(8) 0.7266(5) 0.9929(6) 0.0224(12) Uani 1 1 d . . . . .
C5 C 0.5867(8) 0.8449(6) 0.8346(6) 0.0234(12) Uani 1 1 d . . . . .
H5A H 0.546811 0.911825 0.905860 0.028 Uiso 1 1 calc R . . . .
C10 C 0.6957(8) 0.6433(6) 0.6209(5) 0.0213(11) Uani 1 1 d . . . . .
H10 H 0.732064 0.574903 0.548544 0.026 Uiso 1 1 calc R . . . .
C6 C 0.6194(7) 0.7308(6) 0.8525(5) 0.0194(11) Uani 1 1 d . . . . .
C9 C 0.6907(8) 0.4922(6) 0.7532(6) 0.0260(12) Uani 1 1 d . . . . .
C4 C 0.5959(7) 0.9983(6) 0.7070(5) 0.0214(11) Uani 1 1 d . . . . .
C2 C 0.6659(7) 0.7588(6) 0.6037(5) 0.0195(11) Uani 1 1 d . . . . .
C3 C 0.6119(7) 0.8627(5) 0.7120(5) 0.0192(11) Uani 1 1 d . . . . .
C8 C 0.6727(7) 0.6263(6) 0.7443(6) 0.0217(11) Uani 1 1 d . . . . .
Cl1 Cl 0.1802(2) 0.80935(16) 0.50827(16) 0.0343(4) Uani 1 1 d . . . . .
Cl2 Cl 0.2002(2) 0.48323(17) 0.85194(17) 0.0396(4) Uani 1 1 d . . . . .
O9 O 0.1336(8) 0.6433(7) 0.6786(7) 0.080(2) Uani 1 1 d . . . . .
H9A H 0.167446 0.637602 0.756869 0.120 Uiso 1 1 d R . . . .
H9B H 0.236856 0.686792 0.668729 0.120 Uiso 1 1 d R . . . .
O10 O 1.0535(8) 1.0147(7) 0.6923(9) 0.099(3) Uani 1 1 d . . . . .
H10A H 0.951088 1.025964 0.678418 0.148 Uiso 1 1 d R . . . .
H10B H 1.045848 0.964264 0.738698 0.148 Uiso 1 1 d R . . . .
O11 O 1.0625(9) 0.6862(9) 1.0284(9) 0.128(4) Uani 1 1 d . . . . .
H11A H 0.983197 0.711740 1.059555 0.192 Uiso 1 1 d R . . . .
H11B H 1.007337 0.595640 0.976846 0.192 Uiso 1 1 d R . . . .
O12 O 1.109(2) 0.9150(17) 0.8880(17) 0.111(6) Uani 0.5 1 d . . P . .
H12A H 1.049354 0.828870 0.860794 0.166 Uiso 0.5 1 d R . P . .
H12B H 1.074864 0.949240 0.967154 0.166 Uiso 0.5 1 d R . P . .


_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 O5 1.969(4) 1_554 ?
Cu1 O3 1.995(4) 2_676 ?
Cu1 O7 1.941(4) 2_666 ?
Cu1 O4 2.607(4) 2_676 ?
Cu1 O1 1.941(4) . ?
Cu1 O6 2.611(5) 1_554 ?
Cu1 C7 2.606(5) 1_554 ?
Cu1 C4 2.615(5) 2_676 ?
O5 H5 0.7967 . ?
O5 C7 1.254(7) . ?
O3 C4 1.267(7) . ?
O7 C9 1.286(7) . ?
O2 H2 0.8200 . ?
O2 C1 1.240(7) . ?
O4 H4 0.9168 . ?
O4 C4 1.260(7) . ?
O1 C1 1.270(7) . ?
O6 C7 1.237(7) . ?
O8 H8 0.8200 . ?
O8 C9 1.235(7) . ?
C1 C2 1.506(7) . ?
C7 C6 1.516(7) . ?
C5 H5A 0.9300 . ?
C5 C6 1.376(7) . ?
C5 C3 1.394(7) . ?
C10 H10 0.9300 . ?
C10 C2 1.378(7) . ?
C10 C8 1.398(8) . ?
C6 C8 1.400(8) . ?
C9 C8 1.501(7) . ?
C4 C3 1.495(7) . ?
C2 C3 1.400(7) . ?
O9 H9A 0.8981 . ?
O9 H9B 0.8498 . ?
O10 H10A 0.8498 . ?
O10 H10B 0.8502 . ?
O11 H11A 0.7577 . ?
O11 H11B 0.8909 . ?
O12 H12A 0.8484 . ?
O12 H12B 0.8498 . ?

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
O5 Cu1 O3 86.54(17) 1_554 2_676 ?
O5 Cu1 O4 91.88(16) 1_554 2_676 ?
O5 Cu1 O6 54.93(15) 1_554 1_554 ?
O5 Cu1 C7 27.59(17) 1_554 1_554 ?
O5 Cu1 C4 86.67(16) 1_554 2_676 ?
O3 Cu1 O4 55.71(15) 2_676 2_676 ?
O3 Cu1 O6 91.87(15) 2_676 1_554 ?
O3 Cu1 C7 87.50(16) 2_676 1_554 ?
O3 Cu1 C4 27.99(17) 2_676 2_676 ?
O7 Cu1 O5 91.41(17) 2_666 1_554 ?
O7 Cu1 O3 177.45(18) 2_666 2_676 ?
O7 Cu1 O4 122.93(16) 2_666 2_676 ?
O7 Cu1 O1 90.50(17) 2_666 . ?
O7 Cu1 O6 88.17(16) 2_666 1_554 ?
O7 Cu1 C7 91.37(16) 2_666 1_554 ?
O7 Cu1 C4 150.42(19) 2_666 2_676 ?
O4 Cu1 O6 136.78(14) 2_676 1_554 ?
O4 Cu1 C4 27.92(15) 2_676 2_676 ?
O1 Cu1 O5 177.15(18) . 1_554 ?
O1 Cu1 O3 91.61(17) . 2_676 ?
O1 Cu1 O4 88.86(15) . 2_676 ?
O1 Cu1 O6 123.04(16) . 1_554 ?
O1 Cu1 C7 150.23(19) . 1_554 ?
O1 Cu1 C4 92.71(16) . 2_676 ?
O6 Cu1 C4 114.13(16) 1_554 2_676 ?
C7 Cu1 O4 114.58(16) 1_554 2_676 ?
C7 Cu1 O6 27.43(16) 1_554 1_554 ?
C7 Cu1 C4 100.05(16) 1_554 2_676 ?
Cu1 O5 H5 136.1 1_556 . ?
C7 O5 Cu1 105.8(4) . 1_556 ?
C7 O5 H5 114.4 . . ?
C4 O3 Cu1 104.3(3) . 2_676 ?
C9 O7 Cu1 120.6(4) . 2_666 ?
C1 O2 H2 109.5 . . ?
Cu1 O4 H4 65.1 2_676 . ?
C4 O4 Cu1 76.4(3) . 2_676 ?
C4 O4 H4 140.1 . . ?
C1 O1 Cu1 119.9(4) . . ?
C7 O6 Cu1 76.1(3) . 1_556 ?
C9 O8 H8 109.4 . . ?
O2 C1 O1 126.4(5) . . ?
O2 C1 C2 119.5(5) . . ?
O1 C1 C2 114.1(5) . . ?
O5 C7 Cu1 46.7(3) . 1_556 ?
O5 C7 C6 117.8(5) . . ?
O6 C7 Cu1 76.5(3) . 1_556 ?
O6 C7 O5 122.9(5) . . ?
O6 C7 C6 119.2(5) . . ?
C6 C7 Cu1 161.7(4) . 1_556 ?
C6 C5 H5A 119.2 . . ?
C6 C5 C3 121.6(5) . . ?
C3 C5 H5A 119.2 . . ?
C2 C10 H10 119.2 . . ?
C2 C10 C8 121.6(5) . . ?
C8 C10 H10 119.2 . . ?
C5 C6 C7 117.5(5) . . ?
C5 C6 C8 119.9(5) . . ?
C8 C6 C7 122.5(5) . . ?
O7 C9 C8 114.7(5) . . ?
O8 C9 O7 124.8(5) . . ?
O8 C9 C8 120.4(5) . . ?
O3 C4 Cu1 47.7(3) . 2_676 ?
O3 C4 C3 118.1(5) . . ?
O4 C4 Cu1 75.7(3) . 2_676 ?
O4 C4 O3 122.7(5) . . ?
O4 C4 C3 119.0(5) . . ?
C3 C4 Cu1 160.7(4) . 2_676 ?
C10 C2 C1 119.2(5) . . ?
C10 C2 C3 119.7(5) . . ?
C3 C2 C1 120.8(5) . . ?
C5 C3 C4 118.1(5) . . ?
C5 C3 C2 118.7(5) . . ?
C2 C3 C4 122.9(5) . . ?
C10 C8 C6 118.5(5) . . ?
C10 C8 C9 119.3(5) . . ?
C6 C8 C9 122.0(5) . . ?
H9A O9 H9B 96.0 . . ?
H10A O10 H10B 109.5 . . ?
H11A O11 H11B 99.8 . . ?
H12A O12 H12B 100.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5 H5 Cl2 0.80 2.22 2.854(4) 137.1 . yes
O2 H2 Cl2 0.82 2.05 2.717(5) 138.2 2_666 yes
O4 H4 Cl1 0.92 2.21 2.824(5) 123.8 2_676 yes
O10 H10A O4 0.85 1.91 2.739(7) 165.5 . yes
O10 H10B O12 0.85 1.95 2.75(2) 156.5 . yes
O11 H11A O6 0.76 1.98 2.688(8) 155.6 . yes

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 O5 C7 O6 7.2(6) 1_556 . . . ?
Cu1 O5 C7 C6 -168.0(4) 1_556 . . . ?
Cu1 O3 C4 O4 -10.7(6) 2_676 . . . ?
Cu1 O3 C4 C3 164.0(4) 2_676 . . . ?
Cu1 O7 C9 O8 -22.6(8) 2_666 . . . ?
Cu1 O7 C9 C8 153.6(4) 2_666 . . . ?
Cu1 O4 C4 O3 8.1(5) 2_676 . . . ?
Cu1 O4 C4 C3 -166.5(5) 2_676 . . . ?
Cu1 O1 C1 O2 17.2(8) . . . . ?
Cu1 O1 C1 C2 -161.0(4) . . . . ?
Cu1 O6 C7 O5 -5.4(5) 1_556 . . . ?
Cu1 O6 C7 C6 169.8(5) 1_556 . . . ?
Cu1 C7 C6 C5 28.0(15) 1_556 . . . ?
Cu1 C7 C6 C8 -153.9(10) 1_556 . . . ?
Cu1 C4 C3 C5 -24.1(15) 2_676 . . . ?
Cu1 C4 C3 C2 161.6(9) 2_676 . . . ?
O5 C7 C6 C5 56.7(7) . . . . ?
O5 C7 C6 C8 -125.2(6) . . . . ?
O3 C4 C3 C5 -62.2(7) . . . . ?
O3 C4 C3 C2 123.5(6) . . . . ?
O7 C9 C8 C10 -133.9(6) . . . . ?
O7 C9 C8 C6 40.9(8) . . . . ?
O2 C1 C2 C10 -42.0(8) . . . . ?
O2 C1 C2 C3 143.4(6) . . . . ?
O4 C4 C3 C5 112.7(6) . . . . ?
O4 C4 C3 C2 -61.6(8) . . . . ?
O1 C1 C2 C10 136.3(6) . . . . ?
O1 C1 C2 C3 -38.3(7) . . . . ?
O6 C7 C6 C5 -118.8(6) . . . . ?
O6 C7 C6 C8 59.3(8) . . . . ?
O8 C9 C8 C10 42.5(9) . . . . ?
O8 C9 C8 C6 -142.6(6) . . . . ?
C1 C2 C3 C5 173.5(5) . . . . ?
C1 C2 C3 C4 -12.2(8) . . . . ?
C7 C6 C8 C10 -176.5(5) . . . . ?
C7 C6 C8 C9 8.7(9) . . . . ?
C5 C6 C8 C10 1.6(8) . . . . ?
C5 C6 C8 C9 -173.2(5) . . . . ?
C10 C2 C3 C5 -1.1(8) . . . . ?
C10 C2 C3 C4 173.2(5) . . . . ?
C6 C5 C3 C4 -172.4(5) . . . . ?
C6 C5 C3 C2 2.2(9) . . . . ?
C2 C10 C8 C6 -0.5(9) . . . . ?
C2 C10 C8 C9 174.5(5) . . . . ?
C3 C5 C6 C7 175.7(5) . . . . ?
C3 C5 C6 C8 -2.5(9) . . . . ?
C8 C10 C2 C1 -174.4(5) . . . . ?
C8 C10 C2 C3 0.2(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_HNNU-1beta
_database_code_depnum_ccdc_archive 'CCDC 2132955'
loop_
_audit_author_name
_audit_author_address
'Jun Zhang'
;Anhui Jianzhu University
China
;
_audit_update_record             
;
2022-01-07 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;
_audit_creation_date             2021-10-29
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C20 H8 Cu2 O16, Br, 2(Br0.5 H1.5 O0.75), 3.5(H2 O), 2(H3 O)'
_chemical_formula_sum            'C20 H24 Br2 Cu2 O23'
_chemical_formula_weight         919.29
_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'
Br Br -0.2901 2.4595 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6566(4)
_cell_length_b                   10.5717(5)
_cell_length_c                   10.5825(5)
_cell_angle_alpha                67.116(2)
_cell_angle_beta                 89.982(2)
_cell_angle_gamma                75.517(2)
_cell_volume                     759.56(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2109
_cell_measurement_temperature    101.0
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      2.764
_shelx_estimated_absorpt_T_max   0.637
_shelx_estimated_absorpt_T_min   0.524
_exptl_absorpt_coefficient_mu    4.128
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 12623 reflections, Rint = 0.0582
 (8306 with I > 3sig(I), Rint = 0.0520)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    2.010
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0856
_diffrn_reflns_av_unetI/netI     0.0773
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3109
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.407
_diffrn_reflns_theta_min         2.101
_diffrn_ambient_temperature      101.0
_diffrn_detector                 'Bruker D8 Venture with photon2 CMOS detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture with photon2 CMOS detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    .
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2463
_reflns_number_total             3109
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 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         1.518
_refine_diff_density_min         -1.077
_refine_diff_density_rms         0.235
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3109
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1087
_refine_ls_R_factor_gt           0.0807
_refine_ls_restrained_S_all      1.084
_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)+(0.0615P)²+15.7689P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1862
_refine_ls_wR_factor_ref         0.2049
_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, All O(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C8) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3. Others
 Fixed Sof: Br2(0.5) Br1(0.5) H8(0.5) H3(0.5) H2(0.5) H6(0.5) O9(0.75)
 H9A(0.75) H9B(0.75) O13(0.5) H13A(0.5) H13B(0.5) O10(0.25) H10A(0.25)
 H10B(0.25)
4.a Riding coordinates:
 O3(H3), O11(H11A,H11B), O12(H12A,H12B,H12C), O9(H9A,H9B), O13(H13A,H13B),
 O10(H10A,H10B)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7)
4.c Idealised tetrahedral OH refined as rotating group:
 O8(H8), O2(H2), O6(H6)
;
_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 1.00260(14) 0.76701(10) 0.76408(9) 0.0121(3) Uani 1 1 d . . . . .
Br2 Br 0.3200(3) 0.8074(2) 0.48935(19) 0.0265(4) Uani 0.5 1 d . . P . .
Br1 Br 0.3004(3) 0.4840(2) 0.1506(2) 0.0312(5) Uani 0.5 1 d . . P . .
O4 O 1.0589(8) 1.0272(6) 0.2742(6) 0.0162(12) Uani 1 1 d . . . . .
O7 O 0.9344(8) 0.4366(6) 0.1912(6) 0.0156(12) Uani 1 1 d . . . . .
O5 O 1.0499(8) 0.7316(6) -0.0401(5) 0.0170(12) Uani 1 1 d . . . . .
O8 O 0.6822(8) 0.4402(6) 0.2989(6) 0.0194(13) Uani 1 1 d . . . . .
H8 H 0.596968 0.464173 0.237091 0.029 Uiso 0.5 1 calc GR . P . .
O3 O 0.7680(8) 1.0850(6) 0.3048(6) 0.0187(12) Uani 1 1 d . . . . .
H3 H 0.738477 1.046677 0.381041 0.028 Uiso 0.5 1 d R . P . .
O1 O 0.9483(8) 0.8086(6) 0.5716(5) 0.0155(12) Uani 1 1 d . . . . .
O2 O 0.6987(8) 0.7302(6) 0.6057(6) 0.0187(12) Uani 1 1 d . . . . .
H2 H 0.730367 0.709883 0.688813 0.028 Uiso 0.5 1 calc GR . P . .
O6 O 0.7674(9) 0.7224(7) -0.0576(6) 0.0235(14) Uani 1 1 d . . . . .
H6 H 0.707226 0.673721 -0.002042 0.035 Uiso 0.5 1 calc GR . P . .
O11 O 0.6362(10) 0.3561(9) 0.6835(9) 0.0417(19) Uani 1 1 d . . . A 3
H11A H 0.677951 0.339258 0.613465 0.063 Uiso 1 1 d R . . A 3
H11B H 0.632721 0.276298 0.750025 0.063 Uiso 1 1 d R . . A 3
O12 O 0.4499(11) 1.0165(8) 0.3116(9) 0.054(3) Uani 1 1 d . . . . .
H12A H 0.464638 0.930308 0.373550 0.081 Uiso 1 1 d R . . . .
H12B H 0.339248 1.041368 0.273360 0.081 Uiso 1 1 d R . . . .
H12C H 0.543288 1.055958 0.292940 0.081 Uiso 1 1 d R . . . .
C4 C 0.9159(11) 0.8454(8) 0.1656(8) 0.0136(16) Uani 1 1 d . . . . .
H4 H 0.957153 0.914169 0.092619 0.016 Uiso 1 1 calc R . . . .
C1 C 0.8216(11) 0.7660(8) 0.5349(8) 0.0137(16) Uani 1 1 d . . . . .
C3 C 0.8903(11) 0.8614(8) 0.2884(8) 0.0118(15) Uani 1 1 d . . . . .
C8 C 0.9082(11) 0.9985(8) 0.2933(7) 0.0127(15) Uani 1 1 d . U . . .
C10 C 0.8059(12) 0.4924(9) 0.2474(8) 0.0163(17) Uani 1 1 d . . . . .
C9 C 0.8987(11) 0.7263(8) 0.0067(8) 0.0142(16) Uani 1 1 d . . . . .
C5 C 0.8820(11) 0.7301(8) 0.1473(8) 0.0128(15) Uani 1 1 d . . . . .
C2 C 0.8340(11) 0.7590(8) 0.3980(8) 0.0143(16) Uani 1 1 d . . . . .
C7 C 0.8003(11) 0.6424(8) 0.3805(8) 0.0139(16) Uani 1 1 d . . . . .
H7 H 0.760281 0.573201 0.453908 0.017 Uiso 1 1 calc R . . . .
C6 C 0.8250(12) 0.6269(8) 0.2557(8) 0.0149(16) Uani 1 1 d . . . . .
O9 O 0.4450(12) 0.6757(10) 0.9614(10) 0.034(2) Uani 0.75 1 d . . P B 1
H9A H 0.364599 0.649853 1.016800 0.052 Uiso 0.75 1 d R . P B 1
H9B H 0.396199 0.759193 0.896060 0.052 Uiso 0.75 1 d R . P B 1
O13 O 0.390(2) 0.9223(15) 0.1106(16) 0.039(4) Uani 0.5 1 d . . P . .
H13A H 0.405908 1.003067 0.053625 0.058 Uiso 0.5 1 d R . P . .
H13B H 0.343298 0.932877 0.181965 0.058 Uiso 0.5 1 d R . P . .
O10 O 0.409(4) 0.738(3) 0.042(3) 0.041(8) Uani 0.25 1 d . . P C 2
H10A H 0.374813 0.692620 0.121896 0.062 Uiso 0.25 1 d R . P C 2
H10B H 0.488973 0.779490 0.053186 0.062 Uiso 0.25 1 d R . P C 2


_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 O4 1.980(5) 2_776 ?
Cu1 O7 1.944(5) 2_766 ?
Cu1 O5 1.973(5) 1_556 ?
Cu1 O1 1.931(5) . ?
O4 C8 1.261(10) . ?
O7 C10 1.285(10) . ?
O5 C9 1.265(10) . ?
O8 H8 0.8400 . ?
O8 C10 1.236(10) . ?
O3 H3 0.8112 . ?
O3 C8 1.265(10) . ?
O1 C1 1.285(10) . ?
O2 H2 0.8400 . ?
O2 C1 1.243(9) . ?
O6 H6 0.8400 . ?
O6 C9 1.232(10) . ?
O11 H11A 0.8702 . ?
O11 H11B 0.8699 . ?
O12 H12A 0.8701 . ?
O12 H12B 0.8699 . ?
O12 H12C 0.8994 . ?
C4 H4 0.9500 . ?
C4 C3 1.382(10) . ?
C4 C5 1.390(11) . ?
C1 C2 1.481(10) . ?
C3 C8 1.510(10) . ?
C3 C2 1.400(10) . ?
C10 C6 1.501(11) . ?
C9 C5 1.509(10) . ?
C5 C6 1.400(10) . ?
C2 C7 1.399(10) . ?
C7 H7 0.9500 . ?
C7 C6 1.400(11) . ?
O9 H9A 0.8701 . ?
O9 H9B 0.8701 . ?
O13 H13A 0.8702 . ?
O13 H13B 0.8699 . ?
O10 H10A 0.8703 . ?
O10 H10B 0.8695 . ?

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
O7 Cu1 O4 177.9(2) 2_766 2_776 ?
O7 Cu1 O5 91.2(2) 2_766 1_556 ?
O5 Cu1 O4 86.6(2) 1_556 2_776 ?
O1 Cu1 O4 91.4(2) . 2_776 ?
O1 Cu1 O7 90.7(2) . 2_766 ?
O1 Cu1 O5 177.6(3) . 1_556 ?
C8 O4 Cu1 103.3(5) . 2_776 ?
C10 O7 Cu1 120.0(5) . 2_766 ?
C9 O5 Cu1 104.2(5) . 1_554 ?
C10 O8 H8 109.5 . . ?
C8 O3 H3 106.7 . . ?
C1 O1 Cu1 119.7(5) . . ?
C1 O2 H2 109.5 . . ?
C9 O6 H6 109.5 . . ?
H11A O11 H11B 109.5 . . ?
H12A O12 H12B 104.5 . . ?
H12A O12 H12C 121.0 . . ?
H12B O12 H12C 134.0 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.9(7) . . ?
C5 C4 H4 119.6 . . ?
O1 C1 C2 114.1(7) . . ?
O2 C1 O1 124.9(7) . . ?
O2 C1 C2 121.0(7) . . ?
C4 C3 C8 117.3(7) . . ?
C4 C3 C2 120.2(7) . . ?
C2 C3 C8 122.3(6) . . ?
O4 C8 O3 122.6(7) . . ?
O4 C8 C3 118.5(7) . . ?
O3 C8 C3 118.6(7) . . ?
O7 C10 C6 113.5(7) . . ?
O8 C10 O7 125.6(8) . . ?
O8 C10 C6 120.8(7) . . ?
O5 C9 C5 116.4(7) . . ?
O6 C9 O5 123.6(7) . . ?
O6 C9 C5 120.0(7) . . ?
C4 C5 C9 117.7(7) . . ?
C4 C5 C6 119.7(7) . . ?
C6 C5 C9 122.5(7) . . ?
C3 C2 C1 121.5(7) . . ?
C7 C2 C1 119.2(7) . . ?
C7 C2 C3 119.2(7) . . ?
C2 C7 H7 119.7 . . ?
C2 C7 C6 120.5(7) . . ?
C6 C7 H7 119.7 . . ?
C5 C6 C10 122.0(7) . . ?
C7 C6 C10 118.3(7) . . ?
C7 C6 C5 119.5(7) . . ?
H9A O9 H9B 109.4 . . ?
H13A O13 H13B 109.5 . . ?
H10A O10 H10B 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O8 H8 Br1 0.84 2.38 3.159(6) 155.1 . yes
O3 H3 Br2 0.81 2.40 2.834(6) 114.5 2_676 yes
O2 H2 Br1 0.84 2.16 2.689(6) 120.6 2_666 yes
O6 H6 O9 0.84 2.04 2.628(11) 126.7 1_554 yes
O6 H6 O10 0.84 2.32 2.93(3) 130.1 . yes
O11 H11A Br2 0.87 2.21 2.935(8) 140.5 2_666 yes
O11 H11B O13 0.87 2.10 2.960(17) 172.2 2_666 yes
O12 H12A Br2 0.87 1.97 2.698(7) 139.8 . yes
O12 H12B O4 0.87 2.19 2.989(10) 152.7 1_455 yes
O12 H12B O6 0.87 2.58 3.090(10) 118.3 2_675 yes
O12 H12C O3 0.90 1.83 2.703(10) 161.5 . yes
O9 H9A Br1 0.87 1.95 2.703(9) 143.4 1_556 yes
O9 H9A O5 0.87 2.34 2.932(10) 125.7 1_456 yes
O9 H9B O3 0.87 2.25 3.065(11) 156.2 2_676 yes
O13 H13A O13 0.87 2.37 3.06(3) 136.7 2_675 yes
O13 H13B O12 0.87 2.15 2.756(19) 126.0 . yes
O10 H10A Br1 0.87 2.32 2.82(3) 116.3 . yes
O10 H10B O6 0.87 2.49 2.93(3) 112.2 . yes
O10 H10B O13 0.87 1.83 2.30(4) 111.8 . yes

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_HNNU-1gama
_database_code_depnum_ccdc_archive 'CCDC 2132956'
loop_
_audit_author_name
_audit_author_address
'Jun Zhang'
;Anhui Jianzhu University
China
;
_audit_update_record             
;
2022-01-07 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;
_audit_creation_date             2021-10-29
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H8 Cu2 O16, 2(I), 5(H2 O), 2(H3 O)'
_chemical_formula_sum            'C20 H24 Cu2 I2 O23'
_chemical_formula_weight         1013.27
_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'
I I -0.4742 1.8119 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6629(6)
_cell_length_b                   10.5730(9)
_cell_length_c                   10.5855(9)
_cell_angle_alpha                67.176(3)
_cell_angle_beta                 89.856(3)
_cell_angle_gamma                75.429(3)
_cell_volume                     760.70(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3877
_cell_measurement_temperature    101.0
_cell_measurement_theta_max      29.038
_cell_measurement_theta_min      2.340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.525
_exptl_absorpt_correction_T_max  0.0309
_exptl_absorpt_correction_T_min  0.0108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0880 before and 0.0556 after correction.
The Ratio of minimum to maximum transmission is 0.3495.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    2.212
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.2077
_diffrn_reflns_Laue_measured_fraction_full 0.921
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5427
_diffrn_reflns_point_group_measured_fraction_full 0.921
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.340
_diffrn_ambient_temperature      101.0
_diffrn_detector                 'Bruker D8 Venture with photon2 CMOS detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS detector'
_diffrn_measured_fraction_theta_full 0.921
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture with photon2 CMOS detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    .
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1409
_reflns_number_total             2611
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 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 (Sheldrick, 2015)'
_refine_diff_density_max         1.310
_refine_diff_density_min         -1.204
_refine_diff_density_rms         0.213
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2611
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1361
_refine_ls_R_factor_gt           0.0967
_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)+(0.0130P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2243
_refine_ls_wR_factor_ref         0.2498
_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, All O(H,H,H) groups
2. Restrained distances
 C9-C5
 1.48 with sigma of 0.01
3. Others
 Fixed Sof: I2(0.5) I1(0.5) H8(0.5) H6(0.5) H2(0.5) H3(0.5) O10(0.5) H10A(0.5)
 H10B(0.5)
4.a Riding coordinates:
 O8(H8), O6(H6), O2(H2), O3(H3), O12(H12A,H12B), O9(H9A,H9B), O11(H11A,H11B,
 H11C), O10(H10A,H10B)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.00226(19) 0.76723(16) 0.76385(15) 0.0155(4) Uani 1 1 d . . . . .
I2 I -0.3215(3) 0.1930(3) 0.5102(3) 0.0640(9) Uani 0.5 1 d . . P . .
I1 I -0.2999(4) 0.5159(3) 0.8493(3) 0.0702(9) Uani 0.5 1 d . . P . .
O8 O 0.2994(11) 0.2685(9) 0.3957(9) 0.021(2) Uani 1 1 d . . . . .
H8 H 0.322270 0.247142 0.328305 0.031 Uiso 0.5 1 d R . P . .
O7 O 0.0499(11) 0.1903(9) 0.4293(9) 0.021(2) Uani 1 1 d . . . . .
O5 O -0.0590(10) -0.0257(9) 0.7255(9) 0.0184(19) Uani 1 1 d . . . . .
O6 O 0.2320(11) -0.0843(9) 0.6943(9) 0.023(2) Uani 1 1 d . . . . .
H6 H 0.262864 -0.065507 0.617169 0.035 Uiso 0.5 1 d R . P . .
O1 O 0.0662(11) 0.5635(9) 0.8099(9) 0.021(2) Uani 1 1 d . . . . .
O4 O -0.0512(11) 0.2675(10) 1.0403(9) 0.022(2) Uani 1 1 d . . . . .
O2 O 0.3188(11) 0.5593(9) 0.7012(9) 0.025(2) Uani 1 1 d . . . . .
H2 H 0.389841 0.537792 0.785337 0.037 Uiso 0.5 1 d R . P . .
O3 O 0.2327(12) 0.2805(10) 1.0559(9) 0.025(2) Uani 1 1 d . . . . .
H3 H 0.326673 0.219592 1.054929 0.038 Uiso 0.5 1 d R . P . .
O12 O -0.3653(12) 0.3541(11) 0.6840(12) 0.041(3) Uani 1 1 d . . . . .
H12A H -0.443747 0.433020 0.675740 0.062 Uiso 1 1 d R . . . .
H12B H -0.290437 0.329510 0.636610 0.062 Uiso 1 1 d R . . . .
O9 O 0.5549(12) -0.0213(12) 0.6867(12) 0.050(3) Uani 1 1 d . . . . .
H9A H 0.490776 0.052095 0.628750 0.075 Uiso 1 1 d R . . . .
H9B H 0.571226 -0.000975 0.757190 0.075 Uiso 1 1 d R . . . .
C10 C 0.1803(17) 0.2335(13) 0.4646(13) 0.021(3) Uani 1 1 d . . . . .
C4 C 0.0863(16) 0.1563(13) 0.8339(13) 0.018(3) Uani 1 1 d . . . . .
H4 H 0.043666 0.088551 0.906850 0.022 Uiso 1 1 calc R . . . .
C1 C 0.1930(18) 0.5078(14) 0.7527(14) 0.025(3) Uani 1 1 d . . . . .
C9 C 0.0927(17) 0.0023(12) 0.7095(12) 0.020(3) Uani 1 1 d D . . . .
C3 C 0.1192(16) 0.2682(13) 0.8518(12) 0.018(3) Uani 1 1 d . . . . .
C6 C 0.1686(15) 0.2413(13) 0.6031(13) 0.019(3) Uani 1 1 d . . . . .
C5 C 0.1126(14) 0.1376(11) 0.7133(12) 0.015(3) Uani 1 1 d D . . . .
C8 C 0.1001(19) 0.2743(13) 0.9901(13) 0.024(3) Uani 1 1 d . . . . .
C7 C 0.1975(15) 0.3574(14) 0.6204(13) 0.018(3) Uani 1 1 d . . . . .
H7 H 0.233734 0.428224 0.546195 0.022 Uiso 1 1 calc R . . . .
O11 O 0.5590(15) 0.3194(16) 1.0278(15) 0.088(6) Uani 1 1 d . . . . .
H11A H 0.676098 0.285632 1.047067 0.132 Uiso 1 1 d R . . . .
H11B H 0.482778 0.385582 0.974518 0.132 Uiso 1 1 d R . . . .
H11C H 0.526018 0.299822 1.109977 0.132 Uiso 1 1 d R . . . .
C2 C 0.1746(15) 0.3727(13) 0.7442(14) 0.020(3) Uani 1 1 d . . . . .
O10 O 0.609(2) 0.078(2) 0.8843(19) 0.028(4) Uani 0.5 1 d . . P . .
H10A H 0.602346 -0.008725 0.906646 0.042 Uiso 0.5 1 d R . P . .
H10B H 0.588126 0.117335 0.950536 0.042 Uiso 0.5 1 d R . P . .


_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 O7 1.934(9) 2_566 ?
Cu1 O5 1.993(8) 1_565 ?
Cu1 O1 1.943(9) . ?
Cu1 O4 1.979(9) 2_567 ?
O8 H8 0.8344 . ?
O8 C10 1.208(15) . ?
O7 C10 1.308(15) . ?
O5 C9 1.266(13) . ?
O6 H6 0.8116 . ?
O6 C9 1.275(14) . ?
O1 C1 1.282(16) . ?
O4 C8 1.281(15) . ?
O2 H2 0.9616 . ?
O2 C1 1.247(15) . ?
O3 H3 0.8400 . ?
O3 C8 1.263(16) . ?
O12 H12A 0.8699 . ?
O12 H12B 0.8200 . ?
O9 H9A 0.8123 . ?
O9 H9B 0.8700 . ?
C10 C6 1.501(17) . ?
C4 H4 0.9500 . ?
C4 C3 1.351(18) . ?
C4 C5 1.373(17) . ?
C1 C2 1.507(18) . ?
C9 C5 1.491(9) . ?
C3 C8 1.495(17) . ?
C3 C2 1.399(16) . ?
C6 C5 1.410(15) . ?
C6 C7 1.378(17) . ?
C7 H7 0.9500 . ?
C7 C2 1.386(18) . ?
O11 H11A 0.8701 . ?
O11 H11B 0.7995 . ?
O11 H11C 0.8651 . ?
O10 H10A 0.8703 . ?
O10 H10B 0.9388 . ?

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
O7 Cu1 O5 91.2(4) 2_566 1_565 ?
O7 Cu1 O1 91.5(4) 2_566 . ?
O7 Cu1 O4 177.6(4) 2_566 2_567 ?
O1 Cu1 O5 177.3(4) . 1_565 ?
O1 Cu1 O4 90.9(4) . 2_567 ?
O4 Cu1 O5 86.5(4) 2_567 1_565 ?
C10 O8 H8 121.1 . . ?
C10 O7 Cu1 118.2(8) . 2_566 ?
C9 O5 Cu1 103.4(7) . 1_545 ?
C9 O6 H6 117.4 . . ?
C1 O1 Cu1 120.0(8) . . ?
C8 O4 Cu1 105.0(8) . 2_567 ?
C1 O2 H2 98.3 . . ?
C8 O3 H3 109.6 . . ?
H12A O12 H12B 135.8 . . ?
H9A O9 H9B 105.0 . . ?
O8 C10 O7 126.0(12) . . ?
O8 C10 C6 120.5(11) . . ?
O7 C10 C6 113.5(11) . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.9(10) . . ?
C5 C4 H4 119.1 . . ?
O1 C1 C2 114.0(11) . . ?
O2 C1 O1 125.6(13) . . ?
O2 C1 C2 120.3(12) . . ?
O5 C9 O6 121.7(10) . . ?
O5 C9 C5 119.7(10) . . ?
O6 C9 C5 118.5(10) . . ?
C4 C3 C8 118.3(10) . . ?
C4 C3 C2 120.3(11) . . ?
C2 C3 C8 121.4(11) . . ?
C5 C6 C10 120.8(10) . . ?
C7 C6 C10 119.9(11) . . ?
C7 C6 C5 119.0(11) . . ?
C4 C5 C9 117.6(10) . . ?
C4 C5 C6 119.0(10) . . ?
C6 C5 C9 123.3(10) . . ?
O4 C8 C3 117.8(11) . . ?
O3 C8 O4 121.9(12) . . ?
O3 C8 C3 120.2(12) . . ?
C6 C7 H7 119.4 . . ?
C6 C7 C2 121.2(11) . . ?
C2 C7 H7 119.4 . . ?
H11A O11 H11B 141.8 . . ?
H11A O11 H11C 100.3 . . ?
H11B O11 H11C 108.7 . . ?
C3 C2 C1 122.6(12) . . ?
C7 C2 C1 118.6(11) . . ?
C7 C2 C3 118.6(11) . . ?
H10A O10 H10B 118.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O8 H8 O9 0.83 2.40 3.023(15) 131.7 2_656 yes
O6 H6 O7 0.81 2.75 3.148(12) 112.3 . yes
O3 H3 O9 0.84 2.70 3.093(14) 110.0 2_657 yes
O12 H12A O2 0.87 2.05 2.874(13) 156.8 1_455 yes
O9 H9B O10 0.87 1.90 2.75(2) 168.8 . yes
O11 H11A O4 0.87 2.05 2.892(13) 161.4 1_655 yes
O11 H11C O6 0.87 2.67 3.122(15) 113.4 2_657 yes
O10 H10A O10 0.87 2.72 3.13(4) 110.1 2_657 yes

_olex2_submission_special_instructions 'No special instructions were received'
