# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1856122'
loop_
_audit_author_name
_audit_author_address
'Junwei Ye'
;Dalian University of Technology
China
;
_audit_update_record             
;
2018-07-16 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 Cu O9'
_chemical_formula_weight         325.72

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/C  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.8432(5)
_cell_length_b                   18.8678(13)
_cell_length_c                   10.6835(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 126.782(4)
_cell_angle_gamma                90.00
_cell_volume                     1104.80(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3380
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      32.64

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            BLUE
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.958
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             660
_exptl_absorpt_coefficient_mu    2.021
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6216
_exptl_absorpt_correction_T_max  0.6880
_exptl_absorpt_process_details   'Higashi (1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 'Bruker SMART CCD area'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            6897
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         32.64
_reflns_number_total             3380
_reflns_number_gt                2631
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0750P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3380
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.1193
_refine_ls_wR_factor_gt          0.1020
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu -0.11072(5) -0.226386(14) 0.17921(3) 0.01973(11) Uani 1 1 d . . .
O1 O 0.2590(3) -0.18918(9) 0.5195(2) 0.0292(4) Uani 1 1 d . . .
O2 O -0.0069(3) -0.13788(8) 0.28935(19) 0.0267(4) Uani 1 1 d . . .
O3 O -0.0454(4) 0.12658(10) 0.2331(2) 0.0366(5) Uani 1 1 d . . .
O4 O 0.2120(3) 0.18884(8) 0.44616(19) 0.0247(4) Uani 1 1 d . . .
O5 O 0.7488(4) 0.08430(10) 0.9515(2) 0.0340(4) Uani 1 1 d . . .
H5 H 0.8397 0.0950 1.0460 0.041 Uiso 1 1 d R . .
O6 O 0.7277(4) -0.02927(11) 0.9941(2) 0.0489(6) Uani 1 1 d . . .
O7 O 0.1361(4) -0.21106(10) 0.1402(3) 0.0421(5) Uani 1 1 d . . .
H7A H 0.1659 -0.1686 0.1219 0.051 Uiso 1 1 d R . .
H7B H 0.1600 -0.2493 0.1068 0.051 Uiso 1 1 d R . .
O8 O -0.3086(4) -0.25255(12) 0.2516(2) 0.0398(5) Uani 1 1 d . . .
H8A H -0.2547 -0.2433 0.3467 0.048 Uiso 1 1 d R . .
H8B H -0.4359 -0.2784 0.1866 0.048 Uiso 1 1 d R . .
O9 O -0.4168(3) -0.17080(10) -0.0401(2) 0.0352(4) Uani 1 1 d . . .
H9A H -0.5636 -0.1842 -0.0769 0.042 Uiso 1 1 d R . .
H9B H -0.3624 -0.1264 -0.0165 0.042 Uiso 1 1 d R . .
C1 C 0.2456(4) -0.06270(11) 0.5038(2) 0.0169(4) Uani 1 1 d . . .
C2 C 0.1493(4) -0.00261(11) 0.4089(3) 0.0183(4) Uani 1 1 d . . .
H2 H 0.0352 -0.0076 0.3013 0.022 Uiso 1 1 calc R . .
C3 C 0.2231(4) 0.06452(11) 0.4745(2) 0.0166(4) Uani 1 1 d . . .
C4 C 0.3936(4) 0.07170(11) 0.6365(2) 0.0188(4) Uani 1 1 d . . .
H4 H 0.4425 0.1166 0.6809 0.023 Uiso 1 1 calc R . .
C5 C 0.4895(4) 0.01223(12) 0.7310(2) 0.0193(4) Uani 1 1 d . . .
C6 C 0.4157(4) -0.05515(12) 0.6642(3) 0.0204(4) Uani 1 1 d . . .
H6 H 0.4809 -0.0951 0.7275 0.024 Uiso 1 1 calc R . .
C7 C 0.1630(4) -0.13559(11) 0.4345(3) 0.0179(4) Uani 1 1 d . . .
C8 C 0.1206(4) 0.13034(12) 0.3745(3) 0.0195(4) Uani 1 1 d . . .
C9 C 0.6648(5) 0.01896(12) 0.9035(3) 0.0249(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.02402(19) 0.01247(15) 0.01597(16) -0.00316(9) 0.00836(14) -0.00224(10)
O1 0.0307(10) 0.0151(8) 0.0299(9) 0.0047(7) 0.0118(8) -0.0010(7)
O2 0.0333(10) 0.0155(8) 0.0191(8) -0.0055(6) 0.0091(7) -0.0028(7)
O3 0.0456(11) 0.0221(9) 0.0148(8) 0.0018(7) 0.0034(8) 0.0022(8)
O4 0.0307(9) 0.0118(7) 0.0177(7) 0.0017(6) 0.0070(7) -0.0003(6)
O5 0.0456(11) 0.0215(9) 0.0149(8) -0.0041(7) 0.0075(8) -0.0079(8)
O6 0.0683(16) 0.0234(10) 0.0179(9) 0.0058(8) 0.0059(10) -0.0040(10)
O7 0.0547(13) 0.0253(9) 0.0668(16) -0.0140(10) 0.0473(13) -0.0116(10)
O8 0.0434(12) 0.0478(12) 0.0311(10) -0.0144(10) 0.0239(10) -0.0206(10)
O9 0.0336(10) 0.0243(9) 0.0288(9) 0.0047(8) 0.0085(8) 0.0011(8)
C1 0.0191(10) 0.0127(9) 0.0162(9) -0.0002(7) 0.0091(8) -0.0005(8)
C2 0.0210(11) 0.0137(9) 0.0150(9) -0.0019(8) 0.0081(9) -0.0015(8)
C3 0.0198(10) 0.0107(9) 0.0155(9) 0.0011(7) 0.0086(8) 0.0009(7)
C4 0.0210(11) 0.0138(9) 0.0149(9) -0.0019(8) 0.0073(8) -0.0026(8)
C5 0.0191(11) 0.0167(10) 0.0138(9) -0.0007(8) 0.0055(9) 0.0001(8)
C6 0.0244(11) 0.0140(9) 0.0185(10) 0.0014(8) 0.0106(9) 0.0019(8)
C7 0.0216(11) 0.0110(9) 0.0204(10) -0.0022(8) 0.0121(9) -0.0022(8)
C8 0.0222(11) 0.0156(10) 0.0138(9) -0.0001(8) 0.0071(8) 0.0016(8)
C9 0.0293(13) 0.0170(10) 0.0155(10) -0.0011(8) 0.0065(10) -0.0007(9)

_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 1.9176(16) . ?
Cu1 O4 1.9289(16) 2_545 ?
Cu1 O8 1.982(2) . ?
Cu1 O7 1.988(2) . ?
Cu1 O9 2.2584(17) . ?
O1 C7 1.250(3) . ?
O2 C7 1.265(3) . ?
O3 C8 1.234(3) . ?
O4 C8 1.274(3) . ?
O4 Cu1 1.9289(16) 2 ?
O5 C9 1.327(3) . ?
O5 H5 0.8340 . ?
O6 C9 1.205(3) . ?
O7 H7A 0.8769 . ?
O7 H7B 0.8632 . ?
O8 H8A 0.8666 . ?
O8 H8B 0.8686 . ?
O9 H9A 0.8686 . ?
O9 H9B 0.8904 . ?
C1 C6 1.387(3) . ?
C1 C2 1.395(3) . ?
C1 C7 1.502(3) . ?
C2 C3 1.388(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.399(3) . ?
C3 C8 1.509(3) . ?
C4 C5 1.384(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(3) . ?
C5 C9 1.485(3) . ?
C6 H6 0.9300 . ?

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 O4 174.43(7) . 2_545 ?
O2 Cu1 O8 93.79(8) . . ?
O4 Cu1 O8 91.08(8) 2_545 . ?
O2 Cu1 O7 87.30(8) . . ?
O4 Cu1 O7 88.42(8) 2_545 . ?
O8 Cu1 O7 169.26(9) . . ?
O2 Cu1 O9 90.28(7) . . ?
O4 Cu1 O9 86.57(7) 2_545 . ?
O8 Cu1 O9 95.43(8) . . ?
O7 Cu1 O9 95.25(9) . . ?
C7 O2 Cu1 120.87(15) . . ?
C8 O4 Cu1 117.28(14) . 2 ?
C9 O5 H5 122.0 . . ?
Cu1 O7 H7A 121.3 . . ?
Cu1 O7 H7B 111.1 . . ?
H7A O7 H7B 123.0 . . ?
Cu1 O8 H8A 119.8 . . ?
Cu1 O8 H8B 114.9 . . ?
H8A O8 H8B 124.8 . . ?
Cu1 O9 H9A 115.9 . . ?
Cu1 O9 H9B 99.9 . . ?
H9A O9 H9B 125.1 . . ?
C6 C1 C2 119.7(2) . . ?
C6 C1 C7 119.50(19) . . ?
C2 C1 C7 120.76(19) . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.64(19) . . ?
C2 C3 C8 121.30(19) . . ?
C4 C3 C8 119.06(18) . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 C9 120.9(2) . . ?
C6 C5 C9 119.24(19) . . ?
C1 C6 C5 120.3(2) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
O1 C7 O2 124.1(2) . . ?
O1 C7 C1 120.24(19) . . ?
O2 C7 C1 115.70(18) . . ?
O3 C8 O4 123.1(2) . . ?
O3 C8 C3 121.1(2) . . ?
O4 C8 C3 115.78(18) . . ?
O6 C9 O5 121.9(2) . . ?
O6 C9 C5 124.6(2) . . ?
O5 C9 C5 113.57(19) . . ?

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
O5 H5 O3 0.83 1.76 2.569(2) 164.0 1_656
O7 H7A O5 0.88 2.01 2.867(3) 166.2 3_656
O7 H7B O1 0.86 1.85 2.685(3) 161.6 4
O8 H8A O4 0.87 2.29 3.123(3) 160.2 3_556
O8 H8A O9 0.87 2.63 3.092(3) 114.4 4_556
O8 H8B O1 0.87 1.86 2.707(3) 164.6 4_455
O9 H9A O3 0.87 2.40 3.067(3) 133.5 3_455
O9 H9B O6 0.89 1.91 2.795(3) 169.4 1_454

_diffrn_measured_fraction_theta_max 0.835
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.908
_refine_diff_density_rms         0.109
