# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_160414f4
_database_code_depnum_ccdc_archive 'CCDC 1851893'
_audit_update_record             
;
2018-08-02 deposited with the CCDC.
2018-09-13 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C2 H6 Cu3 O8'
_chemical_formula_moiety         'C2 H6 Cu3 O8'
_chemical_formula_weight         348.70
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   7.0572(7)
_cell_length_b                   9.1203(7)
_cell_length_c                   5.7992(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 105.878(4)
_cell_angle_gamma                90.0000
_cell_volume                     359.02(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    970
_cell_measurement_theta_min      3.70
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    290
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    3.225
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             338.00
_exptl_absorpt_coefficient_mu    8.817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku, ????)'
_exptl_absorpt_correction_T_min  0.138
_exptl_absorpt_correction_T_max  0.414

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      290
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_reflns_number            2569
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         3.742
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       6
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             809
_reflns_number_gt                670
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.0974
_refine_ls_wR_factor_gt          0.0962
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         809
_refine_ls_number_parameters     69
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0507P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         1.01
_refine_diff_density_min         -1.88
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cu Cu 0.3201 1.2651
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 1.00969(8) 0.66132(5) 0.97092(9) 0.0091(2) Uani 1 1 d . . . . .
Cu2 Cu 1.0000 1.0000 1.0000 0.0075(2) Uani 1 2 d S . P . .
O3 O 1.1368(5) 0.8265(3) 1.1544(6) 0.0097(7) Uani 1 1 d . . . . .
O4 O 0.5368(5) 0.6621(3) 0.7037(6) 0.0195(8) Uani 1 1 d . . . . .
O5 O 0.8803(5) 0.4927(3) 0.7831(6) 0.0095(7) Uani 1 1 d . . . . .
O6 O 0.7981(5) 0.8088(3) 0.7951(6) 0.0133(7) Uani 1 1 d . . . . .
C7 C 0.6166(7) 0.7836(4) 0.7281(7) 0.0131(9) Uani 1 1 d . . . . .
H7 H 0.5320 0.8664 0.6927 0.016 Uiso 1 1 calc R U . . .
H3 H 1.247(9) 0.831(6) 1.171(11) 0.04(2) Uiso 1 1 d . . . . .
H5 H 0.771(8) 0.509(5) 0.729(9) 0.020(17) Uiso 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 0.0144(4) 0.0035(3) 0.0084(3) -0.00032(17) 0.0016(3) -0.00052(19)
Cu2 0.0113(5) 0.0039(4) 0.0076(4) 0.0011(2) 0.0033(3) 0.0014(3)
O3 0.0089(18) 0.0072(14) 0.0133(18) -0.0004(10) 0.0033(14) 0.0003(12)
O4 0.0148(19) 0.0191(17) 0.024(2) -0.0017(12) 0.0041(15) -0.0022(13)
O5 0.0105(18) 0.0071(14) 0.0102(16) 0.0016(10) 0.0016(13) 0.0024(12)
O6 0.0084(17) 0.0097(14) 0.0204(19) 0.0009(12) 0.0018(14) -0.0013(12)
C7 0.015(2) 0.015(2) 0.009(2) -0.0004(16) 0.0041(18) 0.0032(18)

#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 O3 1.919(3) . ?
Cu1 O5 1.960(3) . ?
Cu1 O5 2.001(3) 3_767 ?
Cu1 O6 2.061(3) . ?
Cu1 O3 2.256(3) 4_575 ?
Cu1 Cu1 2.9693(9) 3_767 ?
Cu2 O3 1.941(3) 3_777 ?
Cu2 O3 1.941(3) . ?
Cu2 O5 2.043(3) 4_576 ?
Cu2 O5 2.043(3) 2_756 ?
Cu2 O6 2.357(3) . ?
Cu2 O6 2.357(3) 3_777 ?
O3 Cu1 2.256(3) 4_576 ?
O3 H3 0.75(6) . ?
O4 C7 1.233(5) . ?
O5 Cu1 2.001(3) 3_767 ?
O5 Cu2 2.043(3) 2_746 ?
O5 H5 0.76(5) . ?
O6 C7 1.254(6) . ?
C7 H7 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
O3 Cu1 O5 179.87(14) . . ?
O3 Cu1 O5 97.15(14) . 3_767 ?
O5 Cu1 O5 82.89(15) . 3_767 ?
O3 Cu1 O6 85.85(13) . . ?
O5 Cu1 O6 94.18(13) . . ?
O5 Cu1 O6 153.95(14) 3_767 . ?
O3 Cu1 O3 100.53(12) . 4_575 ?
O5 Cu1 O3 79.35(11) . 4_575 ?
O5 Cu1 O3 116.84(12) 3_767 4_575 ?
O6 Cu1 O3 87.75(12) . 4_575 ?
O3 Cu1 Cu1 138.06(10) . 3_767 ?
O5 Cu1 Cu1 41.98(9) . 3_767 ?
O5 Cu1 Cu1 40.91(9) 3_767 3_767 ?
O6 Cu1 Cu1 130.81(9) . 3_767 ?
O3 Cu1 Cu1 100.51(7) 4_575 3_767 ?
O3 Cu2 O3 180.0 3_777 . ?
O3 Cu2 O5 94.67(13) 3_777 4_576 ?
O3 Cu2 O5 85.33(13) . 4_576 ?
O3 Cu2 O5 85.33(13) 3_777 2_756 ?
O3 Cu2 O5 94.67(13) . 2_756 ?
O5 Cu2 O5 180.0 4_576 2_756 ?
O3 Cu2 O6 102.40(13) 3_777 . ?
O3 Cu2 O6 77.60(13) . . ?
O5 Cu2 O6 95.94(12) 4_576 . ?
O5 Cu2 O6 84.06(11) 2_756 . ?
O3 Cu2 O6 77.60(13) 3_777 3_777 ?
O3 Cu2 O6 102.40(13) . 3_777 ?
O5 Cu2 O6 84.06(12) 4_576 3_777 ?
O5 Cu2 O6 95.94(12) 2_756 3_777 ?
O6 Cu2 O6 180.00(15) . 3_777 ?
Cu1 O3 Cu2 106.63(17) . . ?
Cu1 O3 Cu1 105.08(14) . 4_576 ?
Cu2 O3 Cu1 94.40(12) . 4_576 ?
Cu1 O3 H3 115(4) . . ?
Cu2 O3 H3 112(4) . . ?
Cu1 O3 H3 121(5) 4_576 . ?
Cu1 O5 Cu1 97.11(15) . 3_767 ?
Cu1 O5 Cu2 100.89(13) . 2_746 ?
Cu1 O5 Cu2 115.50(15) 3_767 2_746 ?
Cu1 O5 H5 110(4) . . ?
Cu1 O5 H5 125(4) 3_767 . ?
Cu2 O5 H5 105(4) 2_746 . ?
C7 O6 Cu1 125.0(3) . . ?
C7 O6 Cu2 135.8(3) . . ?
Cu1 O6 Cu2 88.69(12) . . ?
O4 C7 O6 126.6(4) . . ?
O4 C7 H7 116.7 . . ?
O6 C7 H7 116.7 . . ?

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 O6 C7 O4 -18.0(6) . . . . ?
Cu2 O6 C7 O4 -150.9(3) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H3 O4 . . 4_676 2.760(5) 0.75(6) 2.01(7) 178(6) no
O5 H5 O4 . . . 2.804(5) 0.76(5) 2.14(5) 146(5) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelx_res_file                  
;

    shelxl.res created by SHELXL-2014/7

TITL 160414f4
CELL  0.71075 7.05720 9.12030 5.79920 90.00000 105.87800 90.00000
ZERR  2 0.00070 0.00070 0.00050 0.00000 0.00400 0.00000
LATT 1
SYMM    -X, .50+Y, .50-Z
SFAC C H CU O
UNIT 4 12 6 16
L.S. 30
FMAP 2
PLAN 25
WPDB -2
HTAB
BOND $H
CONF
LIST 4
TEMP -100.0
ACTA
SIZE 0.400 0.300 0.100
WGHT    0.050700
FVAR       1.99520
CU1   3    1.009686    0.661323    0.970918    11.00000    0.01441    0.00353 =
         0.00839   -0.00032    0.00164   -0.00052
CU2   3    1.000000    1.000000    1.000000    10.50000    0.01130    0.00391 =
         0.00763    0.00112    0.00335    0.00139
O3    4    1.136825    0.826458    1.154385    11.00000    0.00893    0.00715 =
         0.01327   -0.00036    0.00335    0.00027
O4    4    0.536808    0.662102    0.703741    11.00000    0.01481    0.01913 =
         0.02379   -0.00167    0.00411   -0.00216
O5    4    0.880290    0.492727    0.783131    11.00000    0.01055    0.00713 =
         0.01020    0.00159    0.00159    0.00237
O6    4    0.798114    0.808843    0.795055    11.00000    0.00839    0.00968 =
         0.02041    0.00089    0.00179   -0.00127
C7    1    0.616595    0.783599    0.728144    11.00000    0.01513    0.01509 =
         0.00944   -0.00038    0.00412    0.00323
AFIX  43
H7    2    0.531975    0.866435    0.692659    11.00000   -1.20000
AFIX   0
H3    2    1.246556    0.831002    1.171121    11.00000    0.03600
H5    2    0.770810    0.508839    0.729485    11.00000    0.01996
HKLF 4

REM  160414f4
REM R1 =  0.0398 for     670 Fo > 4sig(Fo)  and  0.0436 for all     809 data
REM     69 parameters refined using      0 restraints

END

WGHT      0.0507      0.0000

REM Instructions for potential hydrogen bonds
EQIV $1 x+1, -y+3/2, z+1/2
HTAB O3 O4_$1
HTAB O5 O4

REM Highest difference peak  1.010,  deepest hole -1.879,  1-sigma level  0.351
Q1    1   1.1719  1.0358  1.1692  11.00000  0.05    1.01
Q2    1   0.8383  0.6973  0.8239  11.00000  0.05    0.96
Q3    1   1.1560  0.6637  1.1681  11.00000  0.05    0.92
Q4    1   0.8401  0.6458  0.8208  11.00000  0.05    0.83
Q5    1   1.0000  0.5000  1.0000  10.50000  0.05    0.81
Q6    1   1.0252  0.8273  0.9701  11.00000  0.05    0.78
Q7    1   0.9817  0.8322  0.9904  11.00000  0.05    0.74
Q8    1   0.7733  0.3335  0.6776  11.00000  0.05    0.71
Q9    1   1.2347  1.0028  1.3144  11.00000  0.05    0.67
Q10   1   0.7623  0.6487  0.6817  11.00000  0.05    0.61
Q11   1   0.9184  0.5657  1.0586  11.00000  0.05    0.61
Q12   1   0.9417  0.8173  1.2063  11.00000  0.05    0.60
Q13   1   0.7296  0.5962  0.7519  11.00000  0.05    0.59
Q14   1   0.6427  0.7978  0.6491  11.00000  0.05    0.54
Q15   1   0.7331  0.7420  0.7892  11.00000  0.05    0.53
Q16   1   0.8306  0.6679  0.9983  11.00000  0.05    0.52
Q17   1   0.9337  0.5861  0.6540  11.00000  0.05    0.49
Q18   1   1.3135  0.8460  0.9655  11.00000  0.05    0.48
Q19   1   1.0274  0.7844  1.1490  11.00000  0.05    0.46
Q20   1   1.0279  0.8690  1.1360  11.00000  0.05    0.46
Q21   1   0.9705  0.4433  0.8341  11.00000  0.05    0.46
Q22   1   0.6746  0.9814  0.5322  11.00000  0.05    0.46
Q23   1   0.8020  0.5004  0.9694  11.00000  0.05    0.46
Q24   1   0.7982  0.5607  0.5336  11.00000  0.05    0.45
Q25   1   1.2019  0.8514  1.0090  11.00000  0.05    0.45
;

_shelx_res_checksum              50074
####################################################################### 
# 
# 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_170731f5
_database_code_depnum_ccdc_archive 'CCDC 1859854'
_audit_update_record             
;
2018-08-02 deposited with the CCDC.
2018-09-13 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C H2 Cu O3'
_chemical_formula_moiety         'C H2 Cu O3'
_chemical_formula_weight         125.57
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
_space_group_IT_number           11
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,+Z
#------------------------------------------------------------------------------
_cell_length_a                   3.2574(12)
_cell_length_b                   5.9387(14)
_cell_length_c                   7.246(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 101.805(9)
_cell_angle_gamma                90.0000
_cell_volume                     137.21(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    570
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    130
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            'light blue'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    3.039
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             122.00
_exptl_absorpt_coefficient_mu    7.712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.159
_exptl_absorpt_correction_T_max  0.214

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      130
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            1340
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_min         4.476
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             342
_reflns_number_gt                312
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0755
_refine_ls_wR_factor_gt          0.0740
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         342
_refine_ls_number_parameters     30
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0404P)²+0.2157P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.45
_refine_diff_density_min         -1.14
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cu Cu 0.3201 1.2651
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.5000 0.5000 0.5000 0.0100(2) Uani 1 2 d S . P . .
O2 O 0.1060(9) 0.7500 0.4409(4) 0.0114(6) Uani 1 2 d DS T P . .
O3 O 0.4246(7) 0.4397(5) 0.2293(3) 0.0149(5) Uani 1 1 d . . . . .
C4 C 0.4161(13) 0.2500 0.1517(6) 0.0140(9) Uani 1 2 d S T P . .
H4 H 0.4019 0.2500 0.0222 0.017 Uiso 1 2 calc R U P . .
H2 H 0.048(17) 0.7500 0.317(3) 0.017 Uiso 1 2 d DS U P . .

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 0.0107(3) 0.0080(4) 0.0114(4) -0.00024(16) 0.0024(2) 0.00137(15)
O2 0.0102(14) 0.0116(14) 0.0120(15) 0.000 0.0013(12) 0.000
O3 0.0179(11) 0.0147(11) 0.0121(11) -0.0004(10) 0.0034(9) 0.0020(10)
C4 0.015(2) 0.016(2) 0.011(2) 0.000 0.0040(17) 0.000

#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.9518(19) . ?
Cu1 O2 1.9518(19) 3_666 ?
Cu1 O3 1.960(2) 3_666 ?
Cu1 O3 1.960(2) . ?
Cu1 Cu1 2.9694(7) 2_646 ?
Cu1 Cu1 2.9694(7) 2_656 ?
O2 Cu1 1.9518(19) 2_656 ?
O2 H2 0.88(2) . ?
O3 C4 1.257(3) . ?
C4 O3 1.257(3) 4_565 ?
C4 H4 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 O2 180.0 . 3_666 ?
O2 Cu1 O3 91.31(12) . 3_666 ?
O2 Cu1 O3 88.69(12) 3_666 3_666 ?
O2 Cu1 O3 88.69(12) . . ?
O2 Cu1 O3 91.31(12) 3_666 . ?
O3 Cu1 O3 180.0 3_666 . ?
O2 Cu1 Cu1 139.52(7) . 2_646 ?
O2 Cu1 Cu1 40.48(7) 3_666 2_646 ?
O3 Cu1 Cu1 100.54(8) 3_666 2_646 ?
O3 Cu1 Cu1 79.46(8) . 2_646 ?
O2 Cu1 Cu1 40.48(7) . 2_656 ?
O2 Cu1 Cu1 139.52(7) 3_666 2_656 ?
O3 Cu1 Cu1 79.46(8) 3_666 2_656 ?
O3 Cu1 Cu1 100.54(8) . 2_656 ?
Cu1 Cu1 Cu1 180.0 2_646 2_656 ?
Cu1 O2 Cu1 99.04(13) 2_656 . ?
Cu1 O2 H2 103(2) 2_656 . ?
Cu1 O2 H2 103(2) . . ?
C4 O3 Cu1 126.8(3) . . ?
O3 C4 O3 127.4(4) . 4_565 ?
O3 C4 H4 116.3 . . ?
O3 C4 H4 116.3 4_565 . ?

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 O3 C4 O3 5.4(7) . . . 4_565 ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2 O3 . . 4_575 2.734(4) 0.88(2) 2.37(3) 105(2) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelx_res_file                  
;

    shelxl.res created by SHELXL-2014/7


TITL 170731f5
CELL  0.71075 3.25740 5.93870 7.24600 90.000 101.805 90.000
ZERR  2 0.00120 0.00140 0.00300 0.000 0.009 0.000
LATT 1
SYMM    -X, 1/2+Y,    -Z
SFAC C H CU O
UNIT 2 4 2 6
L.S. 20
FMAP 2
PLAN -25
WPDB -2
REM HTAB
BOND $H
CONF
LIST 4
TEMP 20.0
ACTA
SIZE 0.200 0.200 0.200
DFIX 0.9000 0.0200 O2 H2
HTAB
WGHT    0.040400    0.215700
FVAR       1.42417
CU1   3    0.500000    0.500000    0.500000    10.50000    0.01074    0.00797 =
         0.01138   -0.00024    0.00238    0.00137
O2    4    0.106046    0.750000    0.440855    10.50000    0.01016    0.01158 =
         0.01198    0.00000    0.00129    0.00000
O3    4    0.424621    0.439667    0.229268    11.00000    0.01793    0.01471 =
         0.01208   -0.00041    0.00341    0.00197
C4    1    0.416123    0.250000    0.151708    10.50000    0.01548    0.01557 =
         0.01143    0.00000    0.00399    0.00000
AFIX  43
H4    2    0.401934    0.249999    0.022209    10.50000   -1.20000
AFIX   0
H2    2    0.048454    0.750000    0.316787    10.50000   -1.20000
HKLF 4

REM  170731f5
REM R1 =  0.0296 for     312 Fo > 4sig(Fo)  and  0.0319 for all     342 data
REM     30 parameters refined using      1 restraints

END

WGHT      0.0404      0.2154

REM No hydrogen bonds found for HTAB generation

REM Highest difference peak  0.450,  deepest hole -1.143,  1-sigma level  0.156
Q1    1   0.8191  0.2500  0.5993  10.50000  0.05    0.45
Q2    1   0.3975  0.5346  0.2288  11.00000  0.05    0.41
Q3    1   0.9460  0.5859  0.6599  11.00000  0.05    0.37
Q4    1   0.3227  0.1443  0.3953  11.00000  0.05    0.36
Q5    1   0.9914  0.2500  0.5925  10.50000  0.05    0.35
Q6    1   0.4942  0.5412  0.6633  11.00000  0.05    0.34
Q7    1   0.1839  0.5033  0.6208  11.00000  0.05    0.33
Q8    1   0.7537  0.2500  0.4617  10.50000  0.05    0.32
Q9    1   0.8208  0.1810  0.4685  11.00000  0.05    0.32
Q10   1   0.4978  0.1712  0.5035  11.00000  0.05    0.31
Q11   1  -0.0762  0.2500  0.0818  10.50000  0.05    0.30
Q12   1   0.5345  0.2500 -0.0259  10.50000  0.05    0.30
Q13   1   0.7316  0.2500  0.3219  10.50000  0.05    0.29
Q14   1   0.5904  0.2500 -0.1412  10.50000  0.05    0.29
Q15   1   0.2856  0.6113  0.3619  11.00000  0.05    0.28
Q16   1   0.2028  0.2500  0.4335  10.50000  0.05    0.28
Q17   1   0.9647  0.6326  0.3166  11.00000  0.05    0.28
Q18   1   0.5413  0.5978  0.8359  11.00000  0.05    0.28
Q19   1   0.6947  0.5750  0.7671  11.00000  0.05    0.27
Q20   1   0.3188  0.2500  0.5400  10.50000  0.05    0.26
Q21   1  -0.1175  0.8668  0.1585  11.00000  0.05    0.26
Q22   1   0.2090  0.6386  0.0963  11.00000  0.05    0.25
Q23   1   0.0684  0.5244  0.1156  11.00000  0.05    0.25
Q24   1  -0.0195  0.2500 -0.1221  10.50000  0.05    0.24
Q25   1   0.9372  0.4981  0.4992  11.00000  0.05    0.24
;

_shelx_res_checksum              90037
