# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_160706f9
_database_code_depnum_ccdc_archive 'CCDC 1493335'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2016-10-03 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C4 H6 Cu O6'
_chemical_formula_moiety         'C4 H6 Cu O6'
_chemical_formula_weight         213.63
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   5.1849(14)
_cell_length_b                   7.2517(16)
_cell_length_c                   8.875(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 100.857(5)
_cell_angle_gamma                90.0000
_cell_volume                     327.72(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1371
_cell_measurement_theta_min      4.00
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    2.165
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             214.00
_exptl_absorpt_coefficient_mu    3.311
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  1.000
_exptl_absorpt_correction_T_max  1.000

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

_diffrn_ambient_temperature      173
_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            2886
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_theta_max         27.414
_diffrn_reflns_theta_min         4.677
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             719
_reflns_number_gt                632
_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          0.0234
_refine_ls_R_factor_gt           0.0213
_refine_ls_wR_factor_ref         0.0607
_refine_ls_wR_factor_gt          0.0596
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         719
_refine_ls_number_parameters     56
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0364P)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          0.000
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.57
_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 0.01453(15) Uani 1 2 d S . P . .
O1 O 0.5616(2) 0.35425(16) 0.32861(14) 0.0173(3) Uani 1 1 d . . . . .
O2 O 0.2656(2) 0.29462(16) 0.52756(14) 0.0173(3) Uani 1 1 d . . . . .
O3 O 0.3764(2) 0.14046(16) 0.16572(15) 0.0205(3) Uani 1 1 d . . . . .
C4 C 0.3915(3) 0.2301(2) 0.2868(2) 0.0146(4) Uani 1 1 d . . . . .
C5 C 0.1958(4) 0.1901(3) 0.3896(2) 0.0209(4) Uani 1 1 d . . . . .
H5A H 0.0167 0.2240 0.3365 0.025 Uiso 1 1 calc R U . . .
H5B H 0.1973 0.0569 0.4141 0.025 Uiso 1 1 calc R U . . .
H6 H 0.119(6) 0.311(4) 0.576(3) 0.060(9) 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 0.0138(2) 0.0164(2) 0.0154(2) -0.00323(9) 0.00794(14) -0.00287(9)
O1 0.0152(6) 0.0194(7) 0.0194(7) -0.0032(5) 0.0087(5) -0.0028(4)
O2 0.0167(6) 0.0215(7) 0.0158(7) -0.0031(5) 0.0088(5) -0.0037(5)
O3 0.0172(7) 0.0273(7) 0.0192(8) -0.0071(5) 0.0091(5) -0.0051(5)
C4 0.0119(8) 0.0173(9) 0.0154(10) 0.0007(7) 0.0051(6) 0.0027(6)
C5 0.0197(9) 0.0258(10) 0.0201(11) -0.0078(7) 0.0109(7) -0.0071(7)

#==============================================================================
_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 (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 O1 1.9276(12) 3_666 ?
Cu1 O1 1.9276(12) . ?
Cu1 O2 1.9666(12) . ?
Cu1 O2 1.9666(12) 3_666 ?
Cu1 O3 2.4347(13) 4_666 ?
Cu1 O3 2.4347(13) 2 ?
O1 C4 1.266(2) . ?
O2 C5 1.427(2) . ?
O2 H6 0.95(3) . ?
O3 C4 1.245(2) . ?
O3 Cu1 2.4347(13) 2_545 ?
C4 C5 1.515(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?

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
O1 Cu1 O1 180.00(6) 3_666 . ?
O1 Cu1 O2 96.83(5) 3_666 . ?
O1 Cu1 O2 83.17(5) . . ?
O1 Cu1 O2 83.17(5) 3_666 3_666 ?
O1 Cu1 O2 96.83(5) . 3_666 ?
O2 Cu1 O2 180.0 . 3_666 ?
O1 Cu1 O3 89.18(5) 3_666 4_666 ?
O1 Cu1 O3 90.82(5) . 4_666 ?
O2 Cu1 O3 92.97(5) . 4_666 ?
O2 Cu1 O3 87.03(5) 3_666 4_666 ?
O1 Cu1 O3 90.82(5) 3_666 2 ?
O1 Cu1 O3 89.18(5) . 2 ?
O2 Cu1 O3 87.03(5) . 2 ?
O2 Cu1 O3 92.97(5) 3_666 2 ?
O3 Cu1 O3 180.0 4_666 2 ?
C4 O1 Cu1 114.30(10) . . ?
C5 O2 Cu1 110.98(11) . . ?
C5 O2 H6 110.9(18) . . ?
Cu1 O2 H6 121.9(16) . . ?
C4 O3 Cu1 130.72(11) . 2_545 ?
O3 C4 O1 123.45(15) . . ?
O3 C4 C5 118.67(15) . . ?
O1 C4 C5 117.88(15) . . ?
O2 C5 C4 108.98(14) . . ?
O2 C5 H5A 109.9 . . ?
C4 C5 H5A 109.9 . . ?
O2 C5 H5B 109.9 . . ?
C4 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?

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 O1 -150.40(13) 2_545 . . . ?
Cu1 O3 C4 C5 29.2(2) 2_545 . . . ?
Cu1 O1 C4 O3 169.28(13) . . . . ?
Cu1 O1 C4 C5 -10.36(19) . . . . ?
Cu1 O2 C5 C4 18.79(17) . . . . ?
O3 C4 C5 O2 174.29(15) . . . . ?
O1 C4 C5 O2 -6.1(2) . . . . ?

#==============================================================================
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_566 2.594(2) 0.95(3) 1.65(3) 174(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 160706f9
CELL  0.71075 5.18490 7.25170 8.87500 90.00000 100.85700 90.00000
ZERR  2 0.00140 0.00160 0.00300 0.00000 0.00500 0.00000
LATT 1
SYMM .50-X, .50+Y, .50-Z
SFAC C H CU O
UNIT 8 12 2 12
L.S. 20
FMAP 2
PLAN 25
WPDB -2
HTAB
BOND $H
CONF
LIST 4
TEMP -100.0
ACTA
SIZE 0.200 0.200 0.200
WGHT    0.036400
FVAR       1.43550
CU1   3    0.500000    0.500000    0.500000    10.50000    0.01380    0.01636 =
         0.01544   -0.00323    0.00794   -0.00287
O1    4    0.561580    0.354254    0.328608    11.00000    0.01516    0.01939 =
         0.01939   -0.00318    0.00874   -0.00285
O2    4    0.265567    0.294619    0.527563    11.00000    0.01673    0.02153 =
         0.01580   -0.00313    0.00877   -0.00367
O3    4    0.376377    0.140457    0.165717    11.00000    0.01723    0.02727 =
         0.01921   -0.00708    0.00908   -0.00508
C4    1    0.391463    0.230065    0.286768    11.00000    0.01193    0.01732 =
         0.01543    0.00068    0.00508    0.00271
C5    1    0.195844    0.190128    0.389649    11.00000    0.01974    0.02581 =
         0.02010   -0.00785    0.01094   -0.00714
AFIX  23
H5A   2    0.016715    0.223966    0.336534    11.00000   -1.20000
H5B   2    0.197307    0.056882    0.414077    11.00000   -1.20000
AFIX   0
H6    2    0.118518    0.311169    0.575563    11.00000    0.05999
HKLF 4

REM  160706f9
REM R1 =  0.0213 for     632 Fo > 4sig(Fo)  and  0.0234 for all     719 data
REM     56 parameters refined using      0 restraints

END

WGHT      0.0359      0.0000

REM Instructions for potential hydrogen bonds
EQIV $1 x-1, y, z
HTAB C5 O1_$1
EQIV $2 x-1/2, -y+1/2, z+1/2
HTAB O2 O1_$2
HTAB O2 O3_$2

REM Highest difference peak  0.345,  deepest hole -0.572,  1-sigma level  0.080
Q1    1   0.3791  0.5043  0.3912  11.00000  0.05    0.35
Q2    1   0.3389  0.3482  0.5226  11.00000  0.05    0.33
Q3    1   0.4082  0.1354  0.1346  11.00000  0.05    0.28
Q4    1   0.3048  0.1962  0.3318  11.00000  0.05    0.27
Q5    1   0.7344  0.2971  0.4749  11.00000  0.05    0.26
Q6    1   0.6422  0.3726  0.4361  11.00000  0.05    0.24
Q7    1   0.2029  0.3181  0.5534  11.00000  0.05    0.22
Q8    1   0.2454  0.2661  0.4726  11.00000  0.05    0.22
Q9    1   0.4330  0.3420  0.6677  11.00000  0.05    0.21
Q10   1   0.3279  0.2952  0.1080  11.00000  0.05    0.20
Q11   1   0.2197  0.1406  0.0601  11.00000  0.05    0.20
Q12   1   0.1110  0.3701  0.3325  11.00000  0.05    0.19
Q13   1   0.1133  0.2757  0.2215  11.00000  0.05    0.17
Q14   1   0.1264  0.1930  0.3698  11.00000  0.05    0.16
Q15   1   0.3186  0.2081  0.2040  11.00000  0.05    0.15
Q16   1  -0.1315  0.3590  0.4364  11.00000  0.05    0.15
Q17   1   0.2813  0.0256  0.2029  11.00000  0.05    0.15
Q18   1   0.4184  0.1626  0.2592  11.00000  0.05    0.15
Q19   1   0.1827 -0.0060  0.2222  11.00000  0.05    0.14
Q20   1   0.7003  0.5068  0.3114  11.00000  0.05    0.14
Q21   1   0.1255  0.2829  0.0601  11.00000  0.05    0.14
Q22   1   0.4946  0.4594  0.2391  11.00000  0.05    0.14
Q23   1  -0.0445  0.3169  0.2938  11.00000  0.05    0.13
Q24   1   0.4772  0.5048  0.2565  11.00000  0.05    0.13
Q25   1   0.4604  0.3741  0.2725  11.00000  0.05    0.12
;

_shelx_res_checksum              46008
####################################################################### 
# 
# 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_160707f1
_database_code_depnum_ccdc_archive 'CCDC 1493336'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2016-10-03 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C4 H6 Cu O6'
_chemical_formula_moiety         'C4 H6 Cu O6'
_chemical_formula_weight         213.63
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   5.0794(5)
_cell_length_b                   8.6924(8)
_cell_length_c                   7.7046(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 107.338(3)
_cell_angle_gamma                90.0000
_cell_volume                     324.72(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1365
_cell_measurement_theta_min      4.70
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    230
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.007
_exptl_crystal_density_diffrn    2.185
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             214.00
_exptl_absorpt_coefficient_mu    3.341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.412
_exptl_absorpt_correction_T_max  0.513

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

_diffrn_ambient_temperature      230
_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            2952
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_theta_max         27.469
_diffrn_reflns_theta_min         4.690
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             720
_reflns_number_gt                668
_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          0.0243
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0676
_refine_ls_wR_factor_gt          0.0667
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         720
_refine_ls_number_parameters     56
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0344P)²+0.0985P] 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         0.42
_refine_diff_density_min         -0.48
_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 0.01753(17) Uani 1 2 d S . P . .
O2 O 0.5484(3) 0.66205(14) 0.34247(19) 0.0210(3) Uani 1 1 d . . . . .
O3 O 0.4107(3) 0.89665(15) 0.24420(19) 0.0222(3) Uani 1 1 d . . . . .
O4 O 0.2579(3) 0.64674(15) 0.5633(2) 0.0215(3) Uani 1 1 d . . . . .
C5 C 0.4083(4) 0.7827(2) 0.3426(2) 0.0168(4) Uani 1 1 d . . . . .
C6 C 0.2325(4) 0.7899(2) 0.4704(3) 0.0207(4) Uani 1 1 d . . . . .
H6A H 0.2959 0.8748 0.5588 0.025 Uiso 1 1 calc R U . . .
H6B H 0.0374 0.8089 0.4009 0.025 Uiso 1 1 calc R U . . .
H4 H 0.159(6) 0.632(3) 0.605(3) 0.025(7) 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 0.0229(3) 0.0140(3) 0.0213(3) 0.00231(10) 0.01513(18) 0.00217(10)
O2 0.0265(8) 0.0179(7) 0.0249(8) 0.0031(5) 0.0172(6) 0.0029(5)
O3 0.0267(8) 0.0201(7) 0.0245(7) 0.0072(5) 0.0151(6) 0.0043(5)
O4 0.0277(9) 0.0185(7) 0.0269(8) 0.0049(5) 0.0211(7) 0.0043(6)
C5 0.0166(9) 0.0195(9) 0.0152(9) -0.0007(7) 0.0059(7) -0.0017(7)
C6 0.0252(11) 0.0195(9) 0.0226(10) 0.0060(7) 0.0150(8) 0.0051(8)

#==============================================================================
_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 (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 O2 1.9225(12) 3_666 ?
Cu1 O2 1.9225(12) . ?
Cu1 O4 1.9326(13) . ?
Cu1 O4 1.9326(13) 3_666 ?
O2 C5 1.267(2) . ?
O3 C5 1.250(2) . ?
O4 C6 1.422(2) . ?
O4 H4 0.69(2) . ?
C5 C6 1.515(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?

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 O4 96.52(6) 3_666 . ?
O2 Cu1 O4 83.48(6) . . ?
O2 Cu1 O4 83.48(6) 3_666 3_666 ?
O2 Cu1 O4 96.52(6) . 3_666 ?
O4 Cu1 O4 180.00(7) . 3_666 ?
C5 O2 Cu1 115.35(12) . . ?
C6 O4 Cu1 114.82(11) . . ?
C6 O4 H4 115(2) . . ?
Cu1 O4 H4 128(2) . . ?
O3 C5 O2 123.28(17) . . ?
O3 C5 C6 118.36(16) . . ?
O2 C5 C6 118.35(16) . . ?
O4 C6 C5 107.93(15) . . ?
O4 C6 H6A 110.1 . . ?
C5 C6 H6A 110.1 . . ?
O4 C6 H6B 110.1 . . ?
C5 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O2 C5 O3 -177.99(14) . . . . ?
Cu1 O2 C5 C6 3.0(2) . . . . ?
Cu1 O4 C6 C5 0.7(2) . . . . ?
O3 C5 C6 O4 178.49(16) . . . . ?
O2 C5 C6 O4 -2.4(2) . . . . ?

#==============================================================================
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
O4 H4 O3 . . 4_576 2.581(2) 0.69(3) 1.90(3) 174(3) 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 160707f1
CELL  0.71075 5.07940 8.69240 7.70460 90.00000 107.33800 90.00000
ZERR  2 0.00050 0.00080 0.00080 0.00000 0.00300 0.00000
LATT 1
SYMM .50-X, .50+Y, .50-Z
SFAC C H CU O
UNIT 8 12 2 12
L.S. 20
FMAP 2
PLAN 25
WPDB -2
HTAB
BOND $H
CONF
LIST 4
TEMP -100.0
ACTA
SIZE 0.200 0.200 0.200
WGHT    0.034400    0.098500
FVAR       1.31492
CU1   3    0.500000    0.500000    0.500000    10.50000    0.02289    0.01402 =
         0.02126    0.00231    0.01513    0.00217
O2    4    0.548446    0.662053    0.342466    11.00000    0.02652    0.01789 =
         0.02489    0.00314    0.01719    0.00294
O3    4    0.410665    0.896648    0.244204    11.00000    0.02674    0.02013 =
         0.02446    0.00721    0.01507    0.00429
O4    4    0.257860    0.646741    0.563281    11.00000    0.02769    0.01852 =
         0.02688    0.00495    0.02111    0.00429
C5    1    0.408326    0.782652    0.342568    11.00000    0.01662    0.01946 =
         0.01516   -0.00071    0.00593   -0.00169
C6    1    0.232483    0.789933    0.470420    11.00000    0.02523    0.01949 =
         0.02262    0.00597    0.01495    0.00513
AFIX  23
H6A   2    0.295885    0.874774    0.558752    11.00000   -1.20000
H6B   2    0.037356    0.808882    0.400859    11.00000   -1.20000
AFIX   0
H4    2    0.158528    0.632366    0.605403    11.00000    0.02456
HKLF 4

REM  160707f1
REM R1 =  0.0228 for     668 Fo > 4sig(Fo)  and  0.0243 for all     720 data
REM     56 parameters refined using      0 restraints

END

WGHT      0.0318      0.1228

REM Instructions for potential hydrogen bonds
EQIV $1 x-1/2, -y+3/2, z-1/2
HTAB C6 O4_$1
EQIV $2 x-1/2, -y+3/2, z+1/2
HTAB O4 O3_$2

REM Highest difference peak  0.422,  deepest hole -0.481,  1-sigma level  0.077
Q1    1   0.3224  0.7821  0.4054  11.00000  0.05    0.42
Q2    1   0.5379  0.6033  0.3774  11.00000  0.05    0.26
Q3    1   0.0602  0.6393  0.6666  11.00000  0.05    0.25
Q4    1   0.3716  0.9482  0.2358  11.00000  0.05    0.23
Q5    1   0.4616  0.7066  0.3399  11.00000  0.05    0.22
Q6    1   0.4969  0.3849  0.4996  11.00000  0.05    0.22
Q7    1   0.2429  0.5118  0.4491  11.00000  0.05    0.22
Q8    1   0.4625  0.5981  0.6209  11.00000  0.05    0.21
Q9    1   0.3570  0.6219  0.5088  11.00000  0.05    0.21
Q10   1   0.3664  0.4929  0.5564  11.00000  0.05    0.20
Q11   1   0.4298  0.8779  0.6042  11.00000  0.05    0.20
Q12   1   0.2116  0.6535  0.5862  11.00000  0.05    0.19
Q13   1   0.3603  0.5945  0.5501  11.00000  0.05    0.19
Q14   1  -0.0257  0.7680  0.2619  11.00000  0.05    0.18
Q15   1   0.7845  0.6498  0.4238  11.00000  0.05    0.18
Q16   1   0.3689  0.8498  0.2278  11.00000  0.05    0.18
Q17   1   0.5936  0.6550  0.3082  11.00000  0.05    0.18
Q18   1   0.2600  0.4806  0.7594  11.00000  0.05    0.18
Q19   1   0.4647  0.6783  0.6655  11.00000  0.05    0.17
Q20   1   0.5931  0.8826  0.7534  11.00000  0.05    0.17
Q21   1   0.1727  0.4946  0.5399  11.00000  0.05    0.17
Q22   1  -0.0022  0.6538  0.2807  11.00000  0.05    0.16
Q23   1   0.5895  0.7945  0.6634  11.00000  0.05    0.15
Q24   1   0.5945  0.7054  0.3543  11.00000  0.05    0.15
Q25   1   0.1360  0.7931  0.1126  11.00000  0.05    0.15
;

_shelx_res_checksum              38249
####################################################################### 
# 
# 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_13120501
_database_code_depnum_ccdc_archive 'CCDC 1493337'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2016-10-03 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C4 H6 Cu O6'
_chemical_formula_moiety         'C4 H6 Cu O6'
_chemical_formula_weight         213.63
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   5.201(4)
_cell_length_b                   7.356(5)
_cell_length_c                   8.839(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 101.169(7)
_cell_angle_gamma                90.0000
_cell_volume                     331.8(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    823
_cell_measurement_theta_min      3.60
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    290
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    2.138
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             214.00
_exptl_absorpt_coefficient_mu    3.270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.388
_exptl_absorpt_correction_T_max  0.520

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

_diffrn_ambient_temperature      290
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.706
_diffrn_reflns_number            2376
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# 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).
;
_reflns_number_total             739
_reflns_number_gt                603
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0268
_refine_ls_wR_factor_ref         0.0694
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         739
_refine_ls_number_parameters     64
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0392P)²+0.0000P] 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         0.480
_refine_diff_density_min         -0.470
_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
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Cu Cu 0.3201 1.2651
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.0000 0.0000 0.02239(18) Uani 1.0 2 d . . .
O2 O -0.0579(4) -0.1445(3) 0.1720(2) 0.0250(5) Uani 1.0 4 d . . .
O3 O 0.2359(4) -0.2000(3) -0.0274(2) 0.0252(5) Uani 1.0 4 d . . .
O4 O 0.1249(4) -0.3579(3) 0.3338(2) 0.0307(5) Uani 1.0 4 d . . .
C5 C 0.1102(5) -0.2670(4) 0.2129(3) 0.0226(6) Uani 1.0 4 d . . .
C6 C 0.3042(7) -0.3060(5) 0.1092(4) 0.0312(7) Uani 1.0 4 d . . .
H7 H 0.378(6) -0.183(5) -0.071(4) 0.046(10) Uiso 1.0 4 d . . .
H8 H 0.302(7) -0.446(5) 0.086(5) 0.041(10) Uiso 1.0 4 d . . .
H9 H 0.458(8) -0.266(6) 0.162(5) 0.053(12) Uiso 1.0 4 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_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cu1 0.0234(3) 0.0274(3) 0.0194(3) 0.00415(18) 0.0118(2) 0.00446(18)
O2 0.0240(10) 0.0310(11) 0.0229(10) 0.0047(8) 0.0119(8) 0.0052(8)
O3 0.0262(10) 0.0333(11) 0.0201(10) 0.0065(8) 0.0141(8) 0.0056(8)
O4 0.0285(11) 0.0424(13) 0.0249(11) 0.0085(9) 0.0142(9) 0.0118(9)
C5 0.0197(13) 0.0310(14) 0.0189(14) -0.0031(11) 0.0085(11) 0.0000(11)
C6 0.0324(17) 0.0389(18) 0.0271(16) 0.0113(14) 0.0174(14) 0.0118(13)

#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

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

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Cu1 O2 1.926(2) yes . .
Cu1 O2 1.926(2) yes . 3_555
Cu1 O3 1.961(2) yes . .
Cu1 O3 1.961(2) yes . 3_555
O2 C5 1.258(3) yes . .
O3 C6 1.423(4) yes . .
O4 C5 1.251(4) yes . .
C5 C6 1.516(5) yes . .
O3 H7 0.91(4) no . .
C6 H8 1.05(4) no . .
C6 H9 0.89(4) no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
O2 Cu1 O2 180.00(11) yes . . 3_555
O2 Cu1 O3 83.13(9) yes . . .
O2 Cu1 O3 96.87(9) yes . . 3_555
O2 Cu1 O3 96.87(9) yes 3_555 . .
O2 Cu1 O3 83.13(9) yes 3_555 . 3_555
O3 Cu1 O3 180.00(11) yes . . 3_555
Cu1 O2 C5 114.54(18) yes . . .
Cu1 O3 C6 111.45(18) yes . . .
O2 C5 O4 123.5(3) yes . . .
O2 C5 C6 118.0(3) yes . . .
O4 C5 C6 118.5(3) yes . . .
O3 C6 C5 108.9(3) yes . . .
Cu1 O3 H7 122(3) no . . .
C6 O3 H7 110(2) no . . .
O3 C6 H8 112(2) no . . .
O3 C6 H9 108(3) no . . .
C5 C6 H8 109(3) no . . .
C5 C6 H9 105(3) no . . .
H8 C6 H9 113(3) no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O2 Cu1 O3 C6 -18.40(11) no . . . .
O3 Cu1 O2 C5 15.87(12) no . . . .
O2 Cu1 O3 C6 -161.60(11) no . . 3_555 3_555
O3 Cu1 O2 C5 -164.13(12) no 3_555 . . .
O2 Cu1 O3 C6 161.60(11) no 3_555 . . .
O3 Cu1 O2 C5 164.13(12) no . . 3_555 3_555
O2 Cu1 O3 C6 18.40(11) no 3_555 . 3_555 3_555
O3 Cu1 O2 C5 -15.87(12) no 3_555 . 3_555 3_555
Cu1 O2 C5 O4 170.28(17) no . . . .
Cu1 O2 C5 C6 -9.9(3) no . . . .
Cu1 O3 C6 C5 17.4(3) no . . . .
O2 C5 C6 O3 -5.3(4) no . . . .
O4 C5 C6 O3 174.5(2) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Cu1 C5 2.703(3) no . 3_555
Cu1 C6 2.812(4) no . 3_555
O3 O4 3.548(4) no . .
Cu1 O4 2.439(2) no . 2_555
Cu1 O4 2.439(2) no . 4_444
Cu1 C5 3.391(3) no . 2_555
Cu1 C5 3.391(3) no . 4_444
O2 O3 3.259(4) no . 4_445
O2 O4 3.093(4) no . 2_555
O2 O4 3.123(3) no . 4_444
O2 C6 3.466(5) no . 1_455
O2 C6 3.270(4) no . 2_555
O3 O2 3.259(4) no . 4_544
O3 O4 3.050(4) no . 2_555
O3 O4 3.206(4) no . 4_444
O3 O4 2.597(3) no . 4_544
O3 C5 3.295(4) no . 4_544
O3 C6 3.545(4) no . 4_444
O4 Cu1 2.439(2) no . 2_545
O4 O2 3.093(4) no . 2_545
O4 O2 3.123(3) no . 4_545
O4 O3 3.050(4) no . 2_545
O4 O3 2.597(3) no . 4_445
O4 O3 3.206(4) no . 4_545
O4 C5 3.368(4) no . 2_545
O4 C6 3.344(5) no . 2_545
O4 C6 3.426(5) no . 4_445
C5 Cu1 3.391(3) no . 2_545
C5 O3 3.295(4) no . 4_445
C5 O4 3.368(4) no . 2_555
C6 O2 3.466(5) no . 1_655
C6 O2 3.270(4) no . 2_545
C6 O3 3.545(4) no . 4_545
C6 O4 3.344(5) no . 2_555
C6 O4 3.426(5) no . 4_544
Cu1 H7 2.56(4) no . 3_555
Cu1 H9 3.20(4) no . .
Cu1 H9 3.20(4) no . 3_555
O2 H7 3.43(4) no . .
O2 H7 2.96(4) no . 3_555
O2 H8 3.09(4) no . .
O2 H9 2.84(4) no . .
O4 H8 2.62(4) no . .
O4 H9 2.60(4) no . .
C5 H7 3.16(4) no . .
H7 H8 2.46(5) no . .
H7 H9 2.11(5) no . .
Cu1 H7 3.44(4) no . 1_455
Cu1 H7 3.44(4) no . 3_655
Cu1 H9 3.42(4) no . 2_555
Cu1 H9 3.42(4) no . 4_444
O2 H7 3.29(3) no . 1_455
O2 H7 2.68(4) no . 4_445
O2 H8 2.72(4) no . 2_555
O2 H9 2.66(4) no . 1_455
O2 H9 3.14(4) no . 2_555
O3 H7 3.47(4) no . 3_655
O3 H9 2.86(4) no . 4_444
O4 H7 3.18(4) no . 2_545
O4 H7 1.69(4) no . 4_445
O4 H8 3.12(4) no . 2_555
O4 H9 3.57(4) no . 1_455
O4 H9 3.04(4) no . 2_545
O4 H9 3.31(4) no . 4_445
C5 H7 2.48(4) no . 4_445
C5 H8 2.94(4) no . 2_555
C5 H9 3.34(4) no . 1_455
C6 H8 3.44(4) no . 3_645
H7 Cu1 3.44(4) no . 1_655
H7 O2 3.29(3) no . 1_655
H7 O2 2.68(4) no . 4_544
H7 O3 3.47(4) no . 3_655
H7 O4 3.18(4) no . 2_555
H7 O4 1.69(4) no . 4_544
H7 C5 2.48(4) no . 4_544
H7 H7 3.13(5) no . 3_655
H7 H8 3.21(5) no . 3_645
H7 H9 3.54(6) no . 3_655
H7 H9 2.92(5) no . 4_444
H8 O2 2.72(4) no . 2_545
H8 O4 3.12(4) no . 2_545
H8 C5 2.94(4) no . 2_545
H8 C6 3.44(4) no . 3_645
H8 H7 3.21(5) no . 3_645
H8 H8 3.31(5) no . 3_545
H8 H8 2.89(6) no . 3_645
H8 H9 3.44(6) no . 3_645
H9 Cu1 3.42(4) no . 2_545
H9 O2 2.66(4) no . 1_655
H9 O2 3.14(4) no . 2_545
H9 O3 2.86(4) no . 4_545
H9 O4 3.57(4) no . 1_655
H9 O4 3.04(4) no . 2_555
H9 O4 3.31(4) no . 4_544
H9 C5 3.34(4) no . 1_655
H9 H7 3.54(6) no . 3_655
H9 H7 2.92(5) no . 4_545
H9 H8 3.44(6) no . 3_645

#==============================================================================
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 H7 O4 . . 4_544 2.597(3) 0.909 1.69(4) 175(3) no

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

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_130821
_database_code_depnum_ccdc_archive 'CCDC 1493338'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2016-10-03 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C4 H6 Cu O6'
_chemical_formula_moiety         'C4 H6 Cu O6'
_chemical_formula_weight         213.63
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   5.113(4)
_cell_length_b                   8.672(6)
_cell_length_c                   7.753(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 106.996(10)
_cell_angle_gamma                90.0000
_cell_volume                     328.8(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1020
_cell_measurement_theta_min      3.60
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    290
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    2.158
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             214.00
_exptl_absorpt_coefficient_mu    3.300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.345
_exptl_absorpt_correction_T_max  0.517

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

_diffrn_ambient_temperature      290
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.706
_diffrn_reflns_number            2333
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# 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).
;
_reflns_number_total             755
_reflns_number_gt                628
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0724
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         755
_refine_ls_number_parameters     64
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0375P)²+0.0000P] 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         0.330
_refine_diff_density_min         -0.640
_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
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Cu Cu 0.3201 1.2651
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.0000 0.0000 0.02343(18) Uani 1.0 2 d . . .
O2 O 0.0471(4) 0.1612(2) -0.1579(3) 0.0272(5) Uani 1.0 4 d . . .
O3 O -0.2420(4) 0.1477(2) 0.0624(3) 0.0279(5) Uani 1.0 4 d . . .
O4 O -0.0916(4) 0.3950(2) -0.2582(3) 0.0292(5) Uani 1.0 4 d . . .
C5 C -0.0937(5) 0.2821(3) -0.1595(4) 0.0217(6) Uani 1.0 4 d . . .
C6 C -0.2692(6) 0.2898(3) -0.0320(4) 0.0270(6) Uani 1.0 4 d . . .
H7 H -0.208(5) 0.371(3) 0.045(4) 0.018(7) Uiso 1.0 4 d . . .
H8 H -0.451(8) 0.316(4) -0.091(5) 0.056(11) Uiso 1.0 4 d . . .
H9 H -0.343(6) 0.132(3) 0.106(4) 0.023(9) Uiso 1.0 4 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_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cu1 0.0315(3) 0.0185(3) 0.0297(3) 0.00302(16) 0.0238(3) 0.00326(17)
O2 0.0359(10) 0.0230(9) 0.0331(11) 0.0046(8) 0.0264(9) 0.0054(8)
O3 0.0363(12) 0.0252(10) 0.0342(13) 0.0056(8) 0.0292(10) 0.0072(8)
O4 0.0354(10) 0.0282(10) 0.0321(11) 0.0071(8) 0.0223(9) 0.0108(8)
C5 0.0216(12) 0.0263(13) 0.0202(14) -0.0013(10) 0.0108(10) 0.0004(11)
C6 0.0332(15) 0.0256(14) 0.0308(16) 0.0062(12) 0.0229(13) 0.0066(12)

#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

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

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Cu1 O2 1.919(2) yes . .
Cu1 O2 1.919(2) yes . 3_555
Cu1 O3 1.938(3) yes . .
Cu1 O3 1.938(3) yes . 3_555
O2 C5 1.270(4) yes . .
O3 C6 1.420(4) yes . .
O4 C5 1.244(4) yes . .
C5 C6 1.519(5) yes . .
O3 H9 0.70(4) no . .
C6 H7 0.91(3) no . .
C6 H8 0.94(4) no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
O2 Cu1 O2 180.00(11) yes . . 3_555
O2 Cu1 O3 83.47(10) yes . . .
O2 Cu1 O3 96.53(10) yes . . 3_555
O2 Cu1 O3 96.53(10) yes 3_555 . .
O2 Cu1 O3 83.47(10) yes 3_555 . 3_555
O3 Cu1 O3 180.00(12) yes . . 3_555
Cu1 O2 C5 115.54(19) yes . . .
Cu1 O3 C6 114.7(2) yes . . .
O2 C5 O4 123.3(3) yes . . .
O2 C5 C6 118.1(3) yes . . .
O4 C5 C6 118.6(3) yes . . .
O3 C6 C5 108.1(3) yes . . .
Cu1 O3 H9 127(2) no . . .
C6 O3 H9 116(2) no . . .
O3 C6 H7 111.5(16) no . . .
O3 C6 H8 113(2) no . . .
C5 C6 H7 107.8(19) no . . .
C5 C6 H8 113(3) no . . .
H7 C6 H8 104(3) no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O2 Cu1 O3 C6 0.94(11) no . . . .
O3 Cu1 O2 C5 -2.25(11) no . . . .
O2 Cu1 O3 C6 179.06(11) no . . 3_555 3_555
O3 Cu1 O2 C5 177.75(11) no 3_555 . . .
O2 Cu1 O3 C6 -179.06(11) no 3_555 . . .
O3 Cu1 O2 C5 -177.75(11) no . . 3_555 3_555
O2 Cu1 O3 C6 -0.94(11) no 3_555 . 3_555 3_555
O3 Cu1 O2 C5 2.25(11) no 3_555 . 3_555 3_555
Cu1 O2 C5 O4 -177.98(15) no . . . .
Cu1 O2 C5 C6 3.1(3) no . . . .
Cu1 O3 C6 C5 0.3(3) no . . . .
O2 C5 C6 O3 -2.2(3) no . . . .
O4 C5 C6 O3 178.83(18) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Cu1 C5 2.720(3) no . 3_555
Cu1 C6 2.842(4) no . 3_555
O3 O4 3.533(4) no . .
Cu1 O4 2.533(2) no . 2_444
Cu1 O4 2.533(2) no . 4_555
Cu1 C5 3.413(3) no . 2_444
Cu1 C5 3.413(3) no . 4_555
O2 O3 3.538(4) no . 1_655
O2 O3 3.159(4) no . 4_554
O2 O4 3.208(3) no . 2_444
O2 O4 3.148(3) no . 4_555
O2 C6 3.524(5) no . 1_655
O2 C6 3.326(5) no . 4_554
O3 O2 3.538(4) no . 1_455
O3 O2 3.159(4) no . 4_455
O3 O4 3.149(3) no . 2_444
O3 O4 2.593(4) no . 4_455
O3 O4 3.229(4) no . 4_555
O3 C5 3.243(4) no . 4_455
O3 C5 3.439(4) no . 4_555
O3 C6 3.403(4) no . 4_555
O4 Cu1 2.533(2) no . 2_454
O4 O2 3.208(3) no . 2_454
O4 O2 3.148(3) no . 4_454
O4 O3 3.149(3) no . 2_454
O4 O3 3.229(4) no . 4_454
O4 O3 2.593(4) no . 4_554
O4 C6 3.441(5) no . 4_554
C5 Cu1 3.413(3) no . 2_454
C5 O3 3.439(4) no . 4_454
C5 O3 3.243(4) no . 4_554
C6 O2 3.524(5) no . 1_455
C6 O2 3.326(5) no . 4_455
C6 O3 3.403(4) no . 4_454
C6 O4 3.441(5) no . 4_455
Cu1 H7 3.44(3) no . .
Cu1 H7 3.44(3) no . 3_555
Cu1 H8 3.52(4) no . .
Cu1 H8 3.52(4) no . 3_555
Cu1 H9 2.43(4) no . 3_555
O2 H7 2.95(3) no . .
O2 H8 3.05(4) no . .
O2 H9 3.25(4) no . .
O2 H9 2.93(3) no . 3_555
O4 H7 2.60(3) no . .
O4 H8 2.63(4) no . .
C5 H9 3.01(4) no . .
H7 H9 2.27(4) no . .
H8 H9 2.16(5) no . .
Cu1 H8 3.49(4) no . 2_444
Cu1 H8 3.49(4) no . 4_555
Cu1 H9 3.42(3) no . 1_655
Cu1 H9 3.42(3) no . 3_455
O2 H7 2.94(3) no . 4_554
O2 H8 2.80(4) no . 1_655
O2 H8 3.53(4) no . 2_444
O2 H8 3.37(4) no . 4_554
O2 H9 3.20(3) no . 1_655
O2 H9 2.74(3) no . 4_554
O3 H8 2.68(4) no . 4_555
O3 H9 3.24(3) no . 3_455
O4 H7 2.78(3) no . 3_565
O4 H8 3.22(4) no . 1_655
O4 H8 3.41(4) no . 4_554
O4 H9 3.33(3) no . 2_454
O4 H9 1.89(4) no . 4_554
C5 H7 3.38(3) no . 3_565
C5 H7 3.56(3) no . 4_454
C5 H8 3.18(4) no . 1_655
C5 H9 2.62(4) no . 4_554
C6 H8 3.45(4) no . 4_555
C6 H9 3.48(3) no . 4_454
H7 O2 2.94(3) no . 4_455
H7 O4 2.78(3) no . 3_565
H7 C5 3.38(3) no . 3_565
H7 C5 3.56(3) no . 4_555
H7 H7 3.31(4) no . 3_565
H7 H8 3.30(5) no . 3_465
H7 H8 3.18(4) no . 4_555
H7 H9 3.49(4) no . 2_455
H8 Cu1 3.49(4) no . 2_454
H8 O2 2.80(4) no . 1_455
H8 O2 3.53(4) no . 2_454
H8 O2 3.37(4) no . 4_455
H8 O3 2.68(4) no . 4_454
H8 O4 3.22(4) no . 1_455
H8 O4 3.41(4) no . 4_455
H8 C5 3.18(4) no . 1_455
H8 C6 3.45(4) no . 4_454
H8 H7 3.30(5) no . 3_465
H8 H7 3.18(4) no . 4_454
H8 H8 3.59(5) no . 3_465
H8 H9 2.64(4) no . 4_454
H9 Cu1 3.42(3) no . 1_455
H9 O2 3.20(3) no . 1_455
H9 O2 2.74(3) no . 4_455
H9 O3 3.24(3) no . 3_455
H9 O4 3.33(3) no . 2_444
H9 O4 1.89(4) no . 4_455
H9 C5 2.62(4) no . 4_455
H9 C6 3.48(3) no . 4_555
H9 H7 3.49(4) no . 2_445
H9 H8 2.64(4) no . 4_555
H9 H9 3.00(4) no . 3_455

#==============================================================================
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 H9 O4 . . 4_455 2.593(4) 0.704 1.89(4) 174(3) no

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

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_13110101
_database_code_depnum_ccdc_archive 'CCDC 1507357'
_audit_update_record             
;
2016-09-29 deposited with the CCDC.
2016-10-03 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C4 H6 Cu O6'
_chemical_formula_moiety         'C4 H6 Cu O6'
_chemical_formula_weight         213.63
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   5.101(3)
_cell_length_b                   8.673(5)
_cell_length_c                   7.747(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 106.933(7)
_cell_angle_gamma                90.0000
_cell_volume                     327.9(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    867
_cell_measurement_theta_min      3.60
_cell_measurement_theta_max      27.40
_cell_measurement_temperature    290
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    2.164
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             214.00
_exptl_absorpt_coefficient_mu    3.309
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku, ????)'
_exptl_absorpt_correction_T_min  0.414
_exptl_absorpt_correction_T_max  0.516

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

_diffrn_ambient_temperature      290
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_reflns_number            2384
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         3.616
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             752
_reflns_number_gt                629
_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          0.0378
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0717
_refine_ls_wR_factor_gt          0.0665
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         754
_refine_ls_number_parameters     56
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0326P)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          0.000
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.36
_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 0.02493(18) Uani 1 2 d S . P . .
O2 O 0.4520(4) 0.6611(2) 0.6579(3) 0.0279(5) Uani 1 1 d . . . . .
O3 O 0.9104(4) 0.3950(2) 0.7421(3) 0.0312(5) Uani 1 1 d . . . . .
O4 O 0.7412(4) 0.6476(2) 0.4376(3) 0.0293(5) Uani 1 1 d . . . . .
C5 C 0.5922(5) 0.7811(3) 0.6592(3) 0.0227(6) Uani 1 1 d . . . . .
C6 C 0.7685(6) 0.7893(3) 0.5324(4) 0.0286(6) Uani 1 1 d . . . . .
H6A H 0.7080 0.8758 0.4465 0.034 Uiso 1 1 calc R U . . .
H6B H 0.9625 0.8066 0.6016 0.034 Uiso 1 1 calc R U . . .
H4 H 0.832(7) 0.637(4) 0.390(5) 0.042(11) 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 0.0315(3) 0.0202(3) 0.0317(3) -0.00317(19) 0.0228(2) -0.00309(19)
O2 0.0340(10) 0.0240(11) 0.0352(10) -0.0035(8) 0.0251(9) -0.0041(8)
O3 0.0348(11) 0.0311(12) 0.0354(11) 0.0108(9) 0.0224(9) 0.0081(9)
O4 0.0376(12) 0.0261(12) 0.0359(11) -0.0065(9) 0.0291(10) -0.0059(9)
C5 0.0221(13) 0.0266(16) 0.0216(12) 0.0017(11) 0.0098(10) 0.0020(11)
C6 0.0330(15) 0.0287(16) 0.0323(14) -0.0072(12) 0.0223(13) -0.0069(12)

#==============================================================================
_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 (Sheldrick, 2014)'
_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 O2 1.919(2) 3_666 ?
Cu1 O2 1.919(2) . ?
Cu1 O4 1.932(2) . ?
Cu1 O4 1.932(2) 3_666 ?
O2 C5 1.262(3) . ?
O3 C5 1.251(3) 2_646 ?
O4 C6 1.418(3) . ?
O4 H4 0.68(3) . ?
C5 O3 1.251(3) 2_656 ?
C5 C6 1.515(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?

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 180.00(11) 3_666 . ?
O2 Cu1 O4 96.55(9) 3_666 . ?
O2 Cu1 O4 83.45(9) . . ?
O2 Cu1 O4 83.45(9) 3_666 3_666 ?
O2 Cu1 O4 96.55(9) . 3_666 ?
O4 Cu1 O4 180.00(9) . 3_666 ?
C5 O2 Cu1 115.39(17) . . ?
C6 O4 Cu1 114.74(16) . . ?
C6 O4 H4 115(3) . . ?
Cu1 O4 H4 129(3) . . ?
O3 C5 O2 123.3(2) 2_656 . ?
O3 C5 C6 118.2(2) 2_656 . ?
O2 C5 C6 118.4(2) . . ?
O4 C6 C5 107.9(2) . . ?
O4 C6 H6A 110.1 . . ?
C5 C6 H6A 110.1 . . ?
O4 C6 H6B 110.1 . . ?
C5 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O2 C5 O3 -178.2(2) . . . 2_656 ?
Cu1 O2 C5 C6 3.1(3) . . . . ?
Cu1 O4 C6 C5 0.0(3) . . . . ?
O3 C5 C6 O4 179.2(2) 2_656 . . . ?
O2 C5 C6 O4 -2.0(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
O4 H4 O3 . . 3_766 2.583(4) 0.68(4) 1.91(4) 180(4) 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 13110101
CELL  0.71075 5.10100 8.67300 7.74700 90.00000 106.93300 90.00000
ZERR  2 0.00300 0.00500 0.00500 0.00000 0.00700 0.00000
LATT 1
SYMM .50-X, .50+Y, .50-Z
SFAC C H CU O
UNIT 8 12 2 12
L.S. 20
FMAP 2
PLAN 25
WPDB -2
HTAB
BOND $H
CONF
LIST 4
TEMP -100.0
ACTA
SIZE 0.200 0.200 0.300
WGHT    0.032600
FVAR       2.24923
CU1   3    0.500000    0.500000    0.500000    10.50000    0.03150    0.02024 =
         0.03167   -0.00317    0.02275   -0.00309
O2    4    0.452005    0.661064    0.657907    11.00000    0.03404    0.02395 =
         0.03524   -0.00352    0.02515   -0.00405
O3    4    0.910380    0.394992    0.742105    11.00000    0.03485    0.03110 =
         0.03538    0.01080    0.02242    0.00811
O4    4    0.741169    0.647622    0.437571    11.00000    0.03756    0.02608 =
         0.03589   -0.00648    0.02914   -0.00585
C5    1    0.592203    0.781129    0.659234    11.00000    0.02207    0.02664 =
         0.02155    0.00166    0.00976    0.00197
C6    1    0.768498    0.789345    0.532365    11.00000    0.03302    0.02870 =
         0.03225   -0.00724    0.02227   -0.00692
AFIX  23
H6A   2    0.708012    0.875769    0.446485    11.00000   -1.20000
H6B   2    0.962468    0.806622    0.601626    11.00000   -1.20000
AFIX   0
H4    2    0.832293    0.636641    0.390181    11.00000    0.04190
HKLF 4

REM  13110101
REM R1 =  0.0281 for     629 Fo > 4sig(Fo)  and  0.0378 for all     754 data
REM     56 parameters refined using      0 restraints

END

WGHT      0.0326      0.0000

REM Instructions for potential hydrogen bonds
EQIV $1 x+1/2, -y+3/2, z+1/2
HTAB C6 O4_$1
EQIV $2 -x+2, -y+1, -z+1
HTAB O4 O3_$2

REM Highest difference peak  0.365,  deepest hole -0.359,  1-sigma level  0.078
Q1    1   0.6568  0.7848  0.5922  11.00000  0.05    0.36
Q2    1   0.8989  0.3673  0.6516  11.00000  0.05    0.29
Q3    1   0.5150  0.7082  0.6578  11.00000  0.05    0.28
Q4    1   0.8075  0.4152  0.7492  11.00000  0.05    0.27
Q5    1   0.8876  0.6164  0.7212  11.00000  0.05    0.27
Q6    1   0.8843  0.8664  0.5406  11.00000  0.05    0.26
Q7    1   0.5052  0.6458  0.2992  11.00000  0.05    0.25
Q8    1   0.4342  0.6243  0.5750  11.00000  0.05    0.25
Q9    1   0.8175  0.4995  0.6658  11.00000  0.05    0.25
Q10   1   0.4250  0.7895  0.3363  11.00000  0.05    0.24
Q11   1   0.2504  0.6414  0.5762  11.00000  0.05    0.24
Q12   1   0.7871  0.6508  0.4164  11.00000  0.05    0.23
Q13   1   0.5845  0.8744  0.3736  11.00000  0.05    0.23
Q14   1   1.0415  0.7740  0.6953  11.00000  0.05    0.22
Q15   1   0.4052  0.6387  0.7104  11.00000  0.05    0.22
Q16   1   0.5334  0.6446  0.7307  11.00000  0.05    0.22
Q17   1   0.9670  0.6935  0.6338  11.00000  0.05    0.21
Q18   1   0.5327  0.8131  0.6322  11.00000  0.05    0.20
Q19   1   0.8141  0.6556  0.5144  11.00000  0.05    0.20
Q20   1   0.4741  0.4924  0.6167  11.00000  0.05    0.19
Q21   1   0.8978  0.5023  0.8809  11.00000  0.05    0.19
Q22   1   0.6638  0.7969  0.7221  11.00000  0.05    0.18
Q23   1   1.2160  0.7935  0.4875  11.00000  0.05    0.18
Q24   1   0.6363  0.6184  0.4565  11.00000  0.05    0.18
Q25   1   0.9092  0.6404  0.3344  11.00000  0.05    0.17
;

_shelx_res_checksum              16282
####################################################################### 
# 
# 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_13110501
_database_code_depnum_ccdc_archive 'CCDC 1507358'
_audit_update_record             
;
2016-09-29 deposited with the CCDC.
2016-10-03 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C4 H6 Cu O6'
_chemical_formula_moiety         'C4 H6 Cu O6'
_chemical_formula_weight         213.63
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   5.110(6)
_cell_length_b                   8.6803(10)
_cell_length_c                   7.748(9)
_cell_angle_alpha                90.0000
_cell_angle_beta                 106.730(15)
_cell_angle_gamma                90.0000
_cell_volume                     329.1(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    920
_cell_measurement_theta_min      3.60
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    290
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    2.156
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             214.00
_exptl_absorpt_coefficient_mu    3.297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku, ????)'
_exptl_absorpt_correction_T_min  0.467
_exptl_absorpt_correction_T_max  0.719

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

_diffrn_ambient_temperature      290
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_reflns_number            2361
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         3.612
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             750
_reflns_number_gt                601
_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          0.0367
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0654
_refine_ls_wR_factor_gt          0.0612
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         750
_refine_ls_number_parameters     56
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0329P)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          0.000
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.43
_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 0.02441(17) Uani 1 2 d S . P . .
O2 O 0.5476(4) 0.6609(2) 0.3422(2) 0.0276(4) Uani 1 1 d . . . . .
O3 O 0.2581(4) 0.6479(2) 0.5620(3) 0.0290(5) Uani 1 1 d . . . . .
O4 O 0.4093(4) 0.8952(2) 0.2421(2) 0.0301(5) Uani 1 1 d . . . . .
C5 C 0.4074(5) 0.7819(3) 0.3411(3) 0.0221(5) Uani 1 1 d . . . . .
C6 C 0.2312(6) 0.7901(3) 0.4674(3) 0.0283(6) Uani 1 1 d . . . . .
H6A H 0.2911 0.8764 0.5533 0.034 Uiso 1 1 calc R U . . .
H6B H 0.0379 0.8074 0.3982 0.034 Uiso 1 1 calc R U . . .
H3 H 0.165(6) 0.641(4) 0.609(4) 0.035(10) 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 0.0318(3) 0.0197(3) 0.0311(3) 0.00337(18) 0.0240(2) 0.00332(18)
O2 0.0358(10) 0.0231(10) 0.0343(10) 0.0038(8) 0.0266(9) 0.0038(8)
O3 0.0375(11) 0.0255(10) 0.0369(12) 0.0062(8) 0.0314(10) 0.0061(9)
O4 0.0357(11) 0.0290(11) 0.0341(11) 0.0119(8) 0.0233(8) 0.0078(8)
C5 0.0227(12) 0.0265(14) 0.0207(12) -0.0006(10) 0.0119(10) -0.0007(10)
C6 0.0336(14) 0.0276(14) 0.0323(15) 0.0080(11) 0.0233(12) 0.0075(11)

#==============================================================================
_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 (Sheldrick, 2014)'
_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 O2 1.917(2) . ?
Cu1 O2 1.918(2) 3_666 ?
Cu1 O3 1.936(2) 3_666 ?
Cu1 O3 1.936(2) . ?
O2 C5 1.270(3) . ?
O3 C6 1.422(3) . ?
O3 H3 0.68(3) . ?
O4 C5 1.249(3) . ?
C5 C6 1.510(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?

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 180.00(11) . 3_666 ?
O2 Cu1 O3 96.74(9) . 3_666 ?
O2 Cu1 O3 83.26(9) 3_666 3_666 ?
O2 Cu1 O3 83.26(9) . . ?
O2 Cu1 O3 96.74(9) 3_666 . ?
O3 Cu1 O3 180.0 3_666 . ?
C5 O2 Cu1 115.57(16) . . ?
C6 O3 Cu1 114.92(16) . . ?
C6 O3 H3 112(3) . . ?
Cu1 O3 H3 132(3) . . ?
O4 C5 O2 123.4(2) . . ?
O4 C5 C6 118.2(2) . . ?
O2 C5 C6 118.4(2) . . ?
O3 C6 C5 107.8(2) . . ?
O3 C6 H6A 110.1 . . ?
C5 C6 H6A 110.1 . . ?
O3 C6 H6B 110.1 . . ?
C5 C6 H6B 110.1 . . ?
H6A C6 H6B 108.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O2 C5 O4 -177.91(19) . . . . ?
Cu1 O2 C5 C6 2.7(3) . . . . ?
Cu1 O3 C6 C5 0.1(3) . . . . ?
O4 C5 C6 O3 178.8(2) . . . . ?
O2 C5 C6 O3 -1.8(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_576 2.587(4) 0.68(4) 1.91(4) 175(4) 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 13110501
CELL  0.71075 5.11000 8.68030 7.74800 90.00000 106.73000 90.00000
ZERR  2 0.00600 0.00100 0.00900 0.00000 0.01500 0.00000
LATT 1
SYMM .50-X, .50+Y, .50-Z
SFAC C H CU O
UNIT 8 12 2 12
L.S. 20
FMAP 2
PLAN 25
WPDB -2
HTAB
BOND $H
CONF
LIST 4
TEMP -100.0
ACTA
SIZE 0.100 0.100 0.500
WGHT    0.032900
FVAR       3.05457
CU1   3    0.500000    0.500000    0.500000    10.50000    0.03177    0.01970 =
         0.03113    0.00337    0.02399    0.00332
O2    4    0.547624    0.660898    0.342163    11.00000    0.03579    0.02312 =
         0.03429    0.00375    0.02660    0.00375
O3    4    0.258082    0.647900    0.562037    11.00000    0.03747    0.02553 =
         0.03687    0.00622    0.03136    0.00607
O4    4    0.409336    0.895237    0.242100    11.00000    0.03566    0.02899 =
         0.03406    0.01185    0.02327    0.00778
C5    1    0.407404    0.781916    0.341088    11.00000    0.02269    0.02649 =
         0.02073   -0.00060    0.01193   -0.00068
C6    1    0.231157    0.790110    0.467359    11.00000    0.03358    0.02761 =
         0.03230    0.00802    0.02327    0.00746
AFIX  23
H6A   2    0.291119    0.876363    0.553271    11.00000   -1.20000
H6B   2    0.037929    0.807430    0.398192    11.00000   -1.20000
AFIX   0
H3    2    0.164880    0.641437    0.608778    11.00000    0.03527
HKLF 4

REM  13110501
REM R1 =  0.0264 for     601 Fo > 4sig(Fo)  and  0.0367 for all     750 data
REM     56 parameters refined using      0 restraints

END

WGHT      0.0329      0.0000

REM Instructions for potential hydrogen bonds
EQIV $1 x-1/2, -y+3/2, z-1/2
HTAB C6 O3_$1
EQIV $2 x-1/2, -y+3/2, z+1/2
HTAB O3 O4_$2

REM Highest difference peak  0.320,  deepest hole -0.426,  1-sigma level  0.086
Q1    1   0.1212  0.8619  0.4704  11.00000  0.05    0.32
Q2    1   0.3312  0.7898  0.4001  11.00000  0.05    0.32
Q3    1   0.7391  0.6465  0.4249  11.00000  0.05    0.31
Q4    1   0.5796  0.8901  0.7421  11.00000  0.05    0.28
Q5    1   0.4707  0.6693  0.6508  11.00000  0.05    0.27
Q6    1   0.5552  0.6479  0.2889  11.00000  0.05    0.23
Q7    1   0.4447  0.9971  0.3963  11.00000  0.05    0.23
Q8    1   0.3582  0.8463  0.1426  11.00000  0.05    0.23
Q9    1   0.3318  0.9371  0.2433  11.00000  0.05    0.23
Q10   1   0.5348  0.6409  0.4130  11.00000  0.05    0.23
Q11   1   0.4935  0.9073  0.3124  11.00000  0.05    0.23
Q12   1  -0.2177  0.7861  0.5288  11.00000  0.05    0.23
Q13   1   0.4005  0.8337  0.2556  11.00000  0.05    0.23
Q14   1   0.4883  1.0152  0.5673  11.00000  0.05    0.22
Q15   1   0.0510  0.9652  0.5967  11.00000  0.05    0.22
Q16   1   0.4159  1.0389  0.5282  11.00000  0.05    0.22
Q17   1   0.4673  0.7097  0.3137  11.00000  0.05    0.21
Q18   1   0.0781  0.6246  0.6573  11.00000  0.05    0.21
Q19   1  -0.0354  0.9273  0.4334  11.00000  0.05    0.20
Q20   1   0.0351  0.9489  0.3410  11.00000  0.05    0.20
Q21   1   0.2441  0.6536  0.6061  11.00000  0.05    0.19
Q22   1   0.4543  0.8956  0.6019  11.00000  0.05    0.19
Q23   1   0.5993  0.7840  0.6626  11.00000  0.05    0.18
Q24   1   0.5147  1.0031  0.3395  11.00000  0.05    0.18
Q25   1   0.0413  0.7369  0.3759  11.00000  0.05    0.17
;

_shelx_res_checksum              25125
####################################################################### 
# 
# 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_13093001
_database_code_depnum_ccdc_archive 'CCDC 1507359'
_audit_update_record             
;
2016-09-29 deposited with the CCDC.
2016-10-03 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C4 H6 Cu O6'
_chemical_formula_moiety         'C4 H6 Cu O6'
_chemical_formula_weight         213.63
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   5.108(2)
_cell_length_b                   8.677(3)
_cell_length_c                   7.755(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 106.812(4)
_cell_angle_gamma                90.0000
_cell_volume                     329.0(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    769
_cell_measurement_theta_min      3.60
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    290
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    2.156
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             214.00
_exptl_absorpt_coefficient_mu    3.297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku, ????)'
_exptl_absorpt_correction_T_min  0.381
_exptl_absorpt_correction_T_max  0.517

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

_diffrn_ambient_temperature      290
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_reflns_number            2343
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_min         3.612
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             748
_reflns_number_gt                627
_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          0.0312
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0683
_refine_ls_wR_factor_gt          0.0673
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         747
_refine_ls_number_parameters     56
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0362P)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          0.000
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.65
_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 0.02347(17) Uani 1 2 d S . P . .
O2 O 0.5472(4) 0.3391(2) 0.3418(3) 0.0266(4) Uani 1 1 d . . . . .
O3 O 0.2580(4) 0.3524(2) 0.5622(3) 0.0279(5) Uani 1 1 d . . . . .
O4 O 0.4096(4) 0.10484(19) 0.2416(3) 0.0293(4) Uani 1 1 d . . . . .
C5 C 0.4073(5) 0.2180(3) 0.3406(3) 0.0212(5) Uani 1 1 d . . . . .
C6 C 0.2319(6) 0.2102(3) 0.4678(4) 0.0274(6) Uani 1 1 d . . . . .
H6A H 0.0384 0.1924 0.3991 0.033 Uiso 1 1 calc R U . . .
H6B H 0.2928 0.1241 0.5539 0.033 Uiso 1 1 calc R U . . .
H3 H 0.161(7) 0.364(3) 0.611(4) 0.038(10) 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 0.0292(3) 0.0186(3) 0.0307(3) -0.00347(18) 0.0213(2) -0.00320(17)
O2 0.0324(10) 0.0227(9) 0.0337(11) -0.0053(8) 0.0238(9) -0.0048(8)
O3 0.0349(11) 0.0254(10) 0.0343(11) -0.0063(8) 0.0275(10) -0.0060(8)
O4 0.0334(10) 0.0277(10) 0.0338(11) -0.0114(8) 0.0208(9) -0.0065(8)
C5 0.0195(12) 0.0253(13) 0.0205(13) 0.0007(10) 0.0086(10) 0.0025(10)
C6 0.0311(14) 0.0265(13) 0.0317(15) -0.0080(11) 0.0205(12) -0.0080(11)

#==============================================================================
_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 (Sheldrick, 2014)'
_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 O2 1.9193(17) . ?
Cu1 O2 1.9193(17) 3_666 ?
Cu1 O3 1.9356(18) . ?
Cu1 O3 1.9357(18) 3_666 ?
O2 C5 1.270(3) . ?
O3 C6 1.421(3) . ?
O3 H3 0.71(3) . ?
O4 C5 1.248(3) . ?
C5 C6 1.514(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?

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 180.00(10) . 3_666 ?
O2 Cu1 O3 83.42(8) . . ?
O2 Cu1 O3 96.58(8) 3_666 . ?
O2 Cu1 O3 96.59(8) . 3_666 ?
O2 Cu1 O3 83.42(8) 3_666 3_666 ?
O3 Cu1 O3 180.0 . 3_666 ?
C5 O2 Cu1 115.63(15) . . ?
C6 O3 Cu1 114.70(15) . . ?
C6 O3 H3 115(3) . . ?
Cu1 O3 H3 129(2) . . ?
O4 C5 O2 123.4(2) . . ?
O4 C5 C6 118.6(2) . . ?
O2 C5 C6 118.0(2) . . ?
O3 C6 C5 108.17(19) . . ?
O3 C6 H6A 110.1 . . ?
C5 C6 H6A 110.1 . . ?
O3 C6 H6B 110.1 . . ?
C5 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O2 C5 O4 178.03(19) . . . . ?
Cu1 O2 C5 C6 -2.8(3) . . . . ?
Cu1 O3 C6 C5 -0.4(3) . . . . ?
O4 C5 C6 O3 -178.7(2) . . . . ?
O2 C5 C6 O3 2.1(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_566 2.583(3) 0.71(4) 1.87(4) 179(3) 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 13093001
CELL  0.71075 5.10800 8.67700 7.75500 90.00000 106.81200 90.00000
ZERR  2 0.00200 0.00300 0.00300 0.00000 0.00400 0.00000
LATT 1
SYMM .50-X, .50+Y, .50-Z
SFAC C H CU O
UNIT 8 12 2 12
L.S. 20
FMAP 2
PLAN 25
WPDB -2
HTAB
BOND $H
CONF
LIST 4
TEMP -100.0
ACTA
SIZE 0.200 0.200 0.700
WGHT    0.036200
FVAR       3.93371
CU1   3    0.500000    0.500000    0.500000    10.50000    0.02917    0.01858 =
         0.03066   -0.00347    0.02132   -0.00320
O2    4    0.547197    0.339120    0.341770    11.00000    0.03241    0.02265 =
         0.03373   -0.00533    0.02384   -0.00476
O3    4    0.258023    0.352356    0.562216    11.00000    0.03491    0.02535 =
         0.03433   -0.00633    0.02746   -0.00598
O4    4    0.409605    0.104839    0.241613    11.00000    0.03339    0.02772 =
         0.03382   -0.01137    0.02082   -0.00654
C5    1    0.407336    0.217954    0.340566    11.00000    0.01948    0.02535 =
         0.02048    0.00066    0.00863    0.00246
C6    1    0.231865    0.210175    0.467827    11.00000    0.03106    0.02648 =
         0.03174   -0.00797    0.02054   -0.00799
AFIX  23
H6A   2    0.038358    0.192391    0.399110    11.00000   -1.20000
H6B   2    0.292828    0.124115    0.553922    11.00000   -1.20000
AFIX   0
H3    2    0.161338    0.364050    0.610969    11.00000    0.03846
HKLF 4

REM  13093001
REM R1 =  0.0265 for     627 Fo > 4sig(Fo)  and  0.0312 for all     747 data
REM     56 parameters refined using      0 restraints

END

WGHT      0.0359      0.0000

REM Instructions for potential hydrogen bonds
EQIV $1 x-1/2, -y+1/2, z-1/2
HTAB C6 O3_$1
EQIV $2 x-1/2, -y+1/2, z+1/2
HTAB O3 O4_$2

REM Highest difference peak  0.295,  deepest hole -0.646,  1-sigma level  0.105
Q1    1  -0.1744  0.1436  0.4114  11.00000  0.05    0.29
Q2    1   0.3479  0.2043  0.4159  11.00000  0.05    0.28
Q3    1   0.0243  0.1015  0.4464  11.00000  0.05    0.28
Q4    1   0.3449  0.0573  0.2439  11.00000  0.05    0.28
Q5    1   0.6271  0.0826  0.4285  11.00000  0.05    0.25
Q6    1  -0.0965  0.0757  0.3372  11.00000  0.05    0.23
Q7    1  -0.0427  0.2388  0.2964  11.00000  0.05    0.22
Q8    1  -0.0250 -0.0011  0.3739  11.00000  0.05    0.22
Q9    1   0.5327  0.4857  0.2428  11.00000  0.05    0.21
Q10   1  -0.2153  0.2708  0.2930  11.00000  0.05    0.20
Q11   1   0.4143  0.1136  0.5956  11.00000  0.05    0.20
Q12   1   0.7561  0.2203  0.5305  11.00000  0.05    0.20
Q13   1   0.0756  0.2547  0.2858  11.00000  0.05    0.19
Q14   1   0.2904 -0.0041  0.5915  11.00000  0.05    0.18
Q15   1   0.4673  0.3232  0.6869  11.00000  0.05    0.18
Q16   1   0.7939  0.3419  0.4568  11.00000  0.05    0.18
Q17   1   0.6038  0.3432  0.3004  11.00000  0.05    0.18
Q18   1   0.2543 -0.0034  0.1477  11.00000  0.05    0.17
Q19   1   0.1658 -0.0773  0.4737  11.00000  0.05    0.17
Q20   1   0.5479  0.2715  0.3615  11.00000  0.05    0.16
Q21   1  -0.0052  0.1543  0.5217  11.00000  0.05    0.16
Q22   1   0.5132 -0.0011  0.3669  11.00000  0.05    0.15
Q23   1   0.5161  0.2162  0.6422  11.00000  0.05    0.15
Q24   1   0.5032  0.4050  0.3625  11.00000  0.05    0.15
Q25   1   0.0668  0.0607  0.2370  11.00000  0.05    0.15
;

_shelx_res_checksum              93818
