# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_kw25
_database_code_depnum_ccdc_archive 'CCDC 1044116'
_audit_update_record             
;
2015-01-16 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 Cu2 O12,2 H2 O'
_chemical_formula_sum            'C10 H14 Cu2 O14'
_chemical_formula_weight         485.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5120(10)
_cell_length_b                   6.9010(10)
_cell_length_c                   9.328(2)
_cell_angle_alpha                95.448(10)
_cell_angle_beta                 108.706(8)
_cell_angle_gamma                108.090(8)
_cell_volume                     368.51(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    240(2)
_cell_measurement_reflns_used    32
_cell_measurement_theta_min      10.0
_cell_measurement_theta_max      12.5

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.187
_exptl_crystal_F_000             244
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    2.968
_shelx_estimated_absorpt_T_min   0.307
_shelx_estimated_absorpt_T_max   0.890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.588
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_process_details   SHELXTL
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      240(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Stoe-Siemens four-circle diffractometer'
_diffrn_measurement_method       'ω/θ scans with on-line profile fitting'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2592
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.361
_diffrn_reflns_theta_max         25.002
_diffrn_reflns_theta_full        25.002
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1296
_reflns_number_gt                1249
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Stoe DIF4'
_computing_cell_refinement       'Stoe DIF4'
_computing_data_reduction        'local programs'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  SHELXL-2014/7
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0399P)²+0.4199P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_extinction_coef       0.016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1296
_refine_ls_number_parameters     137
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_ref         0.0700
_refine_ls_wR_factor_gt          0.0688
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Cu Cu 0.00502(5) 0.26574(4) 0.13393(3) 0.01161(17) Uani 1 1 d . . . . .
C1 C 0.3626(4) 0.8823(4) 0.3489(3) 0.0104(5) Uani 1 1 d . . . . .
C2 C 0.5903(4) 1.0185(4) 0.3827(3) 0.0100(5) Uani 1 1 d . . . . .
C3 C 0.7242(4) 1.1352(4) 0.5326(3) 0.0117(5) Uani 1 1 d . . . . .
H3 H 0.8762 1.2278 0.5544 0.014 Uiso 1 1 calc R U . . .
C4 C 0.1982(4) 0.7654(4) 0.1868(3) 0.0114(5) Uani 1 1 d . . . . .
C5 C 0.7089(4) 1.0327(4) 0.2664(3) 0.0117(5) Uani 1 1 d . . . . .
O1 O 0.0371(3) 0.5999(3) 0.16939(19) 0.0146(4) Uani 1 1 d . . . . .
O2 O 0.2297(3) 0.8515(3) 0.0761(2) 0.0165(4) Uani 1 1 d . . . . .
O3 O 0.7477(3) 0.8788(3) 0.2199(2) 0.0198(4) Uani 1 1 d . . . . .
O4 O 0.7741(3) 1.2106(3) 0.2321(2) 0.0148(4) Uani 1 1 d . . . . .
O5 O 0.2489(3) 0.3179(3) 0.3382(2) 0.0181(4) Uani 1 1 d D . . . .
H5A H 0.243(5) 0.361(5) 0.423(2) 0.027 Uiso 1 1 d D U . . .
H5B H 0.382(3) 0.385(4) 0.342(3) 0.027 Uiso 1 1 d D U . . .
O6 O 0.2657(4) 0.2776(4) 0.0646(2) 0.0295(5) Uani 1 1 d D . . . .
H6A H 0.243(7) 0.287(6) -0.0265(19) 0.044 Uiso 1 1 d D U . . .
H6B H 0.320(7) 0.184(5) 0.083(4) 0.044 Uiso 1 1 d D U . . .
O7 O 0.6921(3) 0.5450(3) 0.3652(2) 0.0180(4) Uani 1 1 d D . . . .
H7A H 0.723(6) 0.451(3) 0.324(3) 0.027 Uiso 1 1 d D U . . .
H7B H 0.711(6) 0.643(3) 0.319(3) 0.027 Uiso 1 1 d D U . . .


_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
Cu O1 2.2319(17) . ?
Cu O2 1.9592(18) 2_565 ?
Cu O4 1.9589(18) 1_445 ?
Cu O5 1.9636(18) . ?
Cu O6 1.984(2) . ?
C1 C2 1.400(3) . ?
C1 C3 1.393(3) 2_676 ?
C1 C4 1.509(3) . ?
C2 C3 1.390(3) . ?
C2 C5 1.514(3) . ?
C3 C1 1.393(3) 2_676 ?
C3 H3 0.940 . ?
C4 O1 1.242(3) . ?
C4 O2 1.280(3) . ?
C5 O3 1.238(3) . ?
C5 O4 1.276(3) . ?
O2 Cu 1.9592(18) 2_565 ?
O4 Cu 1.9590(18) 1_665 ?
O5 H5A 0.837(10) . ?
O5 H5B 0.836(10) . ?
O6 H6A 0.827(10) . ?
O6 H6B 0.835(10) . ?
O7 H7A 0.829(10) . ?
O7 H7B 0.833(10) . ?

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 Cu O2 102.39(7) . 2_565 ?
O1 Cu O4 88.40(7) . 1_445 ?
O1 Cu O5 91.22(7) . . ?
O1 Cu O6 101.58(9) . . ?
O2 Cu O4 93.62(8) 2_565 1_445 ?
O2 Cu O5 166.19(8) 2_565 . ?
O2 Cu O6 93.15(8) 2_565 . ?
O4 Cu O5 89.02(8) 1_445 . ?
O4 Cu O6 166.45(9) 1_445 . ?
O5 Cu O6 81.70(8) . . ?
C2 C1 C3 119.0(2) . 2_676 ?
C2 C1 C4 123.1(2) . . ?
C3 C1 C4 117.7(2) 2_676 . ?
C1 C2 C3 119.7(2) . . ?
C1 C2 C5 123.0(2) . . ?
C3 C2 C5 117.1(2) . . ?
C1 C3 C2 121.3(2) 2_676 . ?
C1 C3 H3 119.3 2_676 . ?
C2 C3 H3 119.3 . . ?
C1 C4 O1 119.0(2) . . ?
C1 C4 O2 116.5(2) . . ?
O1 C4 O2 124.4(2) . . ?
C2 C5 O3 118.7(2) . . ?
C2 C5 O4 116.0(2) . . ?
O3 C5 O4 125.2(2) . . ?
Cu O1 C4 132.93(16) . . ?
Cu O2 C4 119.01(16) 2_565 . ?
Cu O4 C5 117.99(16) 1_665 . ?
Cu O5 H5A 125(2) . . ?
Cu O5 H5B 113(2) . . ?
H5A O5 H5B 106.7(16) . . ?
Cu O6 H6A 116(3) . . ?
Cu O6 H6B 115(3) . . ?
H6A O6 H6B 108.9(17) . . ?
H7A O7 H7B 108.6(17) . . ?

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
C3 C1 C2 C3 -0.8(4) 2_676 . . . ?
C3 C1 C2 C5 173.7(2) 2_676 . . . ?
C4 C1 C2 C3 174.1(2) . . . . ?
C4 C1 C2 C5 -11.4(4) . . . . ?
C1 C2 C3 C1 0.8(4) . . . 2_676 ?
C5 C2 C3 C1 -174.0(2) . . . 2_676 ?
C2 C1 C4 O1 155.1(2) . . . . ?
C2 C1 C4 O2 -28.2(3) . . . . ?
C3 C1 C4 O1 -29.9(3) 2_676 . . . ?
C3 C1 C4 O2 146.8(2) 2_676 . . . ?
C1 C2 C5 O3 -64.6(3) . . . . ?
C1 C2 C5 O4 119.8(3) . . . . ?
C3 C2 C5 O3 110.1(3) . . . . ?
C3 C2 C5 O4 -65.6(3) . . . . ?
C1 C4 O1 Cu -92.2(2) . . . . ?
O2 C4 O1 Cu 91.3(3) . . . . ?
C1 C4 O2 Cu -170.09(16) . . . 2_565 ?
O1 C4 O2 Cu 6.4(3) . . . 2_565 ?
C2 C5 O4 Cu 162.22(16) . . . 1_665 ?
O3 C5 O4 Cu -13.1(3) . . . 1_665 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5A O7 0.837(10) 1.884(14) 2.701(3) 165(3) 2_666
O5 H5B O7 0.836(10) 1.904(11) 2.739(3) 176(3) .
O6 H6A O1 0.827(10) 2.29(3) 2.827(3) 123(3) 2_565
O6 H6A O3 0.827(10) 2.07(3) 2.732(3) 137(3) 2_665
O6 H6B O2 0.835(10) 2.17(3) 2.891(3) 144(4) 1_545
O7 H7A O4 0.829(10) 1.966(10) 2.793(3) 175(3) 1_545
O7 H7B O3 0.833(10) 1.937(10) 2.768(3) 176(3) .

_refine_diff_density_max         0.459
_refine_diff_density_min         -0.697
_refine_diff_density_rms         0.094

_exptl_crystal_recrystallization_method 
'Obtained direct from slow diffusion synthesis'
####################################################################### 
# 
# 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_wc57
_database_code_depnum_ccdc_archive 'CCDC 1044117'
_audit_update_record             
;
2015-01-16 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H14 Cu2 O14,4 H2 O'
_chemical_formula_sum            'C10 H22 Cu2 O18'
_chemical_formula_weight         557.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.1518(8)
_cell_length_b                   18.1413(11)
_cell_length_c                   9.5816(6)
_cell_angle_alpha                90
_cell_angle_beta                 113.503(2)
_cell_angle_gamma                90
_cell_volume                     1937.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    6591
_cell_measurement_theta_min      2.318
_cell_measurement_theta_max      28.133

_exptl_crystal_description       Block
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.911
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.287
_shelx_estimated_absorpt_T_min   0.645
_shelx_estimated_absorpt_T_max   0.658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.640
_exptl_absorpt_correction_T_max  0.660
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker SMART 1K CCD diffractometer'
_diffrn_measurement_method       'narrow-frame ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7999
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.145
_diffrn_reflns_theta_max         28.179
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2253
_reflns_number_gt                2063
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  SHELXL-2014/7
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0285P)²+2.8396P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2253
_refine_ls_number_parameters     166
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0235
_refine_ls_wR_factor_ref         0.0608
_refine_ls_wR_factor_gt          0.0593
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Cu Cu 0.22001(2) 0.55931(2) 0.33081(2) 0.01032(8) Uani 1 1 d . . . . .
C1 C 0.44016(15) 0.71960(9) 0.24300(19) 0.0112(3) Uani 1 1 d . . . . .
C2 C 0.38191(15) 0.78628(9) 0.23552(19) 0.0113(3) Uani 1 1 d . . . . .
H2 H 0.3011 0.7862 0.2261 0.014 Uiso 1 1 calc R U . . .
C3 C 0.43980(14) 0.85345(9) 0.24163(18) 0.0098(3) Uani 1 1 d . . . . .
C4 C 0.37234(15) 0.64845(9) 0.2286(2) 0.0131(3) Uani 1 1 d . . . . .
C5 C 0.36641(15) 0.92225(9) 0.22504(19) 0.0097(3) Uani 1 1 d . . . . .
O1 O 0.37017(13) 0.60314(7) 0.13036(17) 0.0231(3) Uani 1 1 d . . . . .
O2 O 0.32068(12) 0.64135(7) 0.32001(15) 0.0164(3) Uani 1 1 d . . . . .
O3 O 0.29707(11) 0.92515(7) 0.29231(15) 0.0145(3) Uani 1 1 d . . . . .
O4 O 0.37426(11) 0.97418(6) 0.13968(14) 0.0114(2) Uani 1 1 d . . . . .
O5 O 0.34838(12) 0.53638(7) 0.52782(16) 0.0179(3) Uani 1 1 d D . . . .
H5A H 0.3523(19) 0.4945(7) 0.564(3) 0.027 Uiso 1 1 d D U . . .
H5B H 0.4162(12) 0.5547(11) 0.557(3) 0.027 Uiso 1 1 d D U . . .
O6 O 0.10433(12) 0.57889(8) 0.12393(15) 0.0181(3) Uani 1 1 d D . . . .
H6A H 0.1067(19) 0.5594(12) 0.0470(19) 0.027 Uiso 1 1 d D U . . .
H6B H 0.0341(11) 0.5906(14) 0.107(2) 0.027 Uiso 1 1 d D U . . .
O7 O 0.11551(12) 0.63051(7) 0.42583(14) 0.0145(3) Uani 1 1 d D . . . .
H7A H 0.1516(19) 0.6223(11) 0.5185(12) 0.022 Uiso 1 1 d D U . . .
H7B H 0.114(2) 0.6766(6) 0.414(2) 0.022 Uiso 1 1 d D U . . .
O8 O 0.55669(13) 0.61173(9) 0.61276(18) 0.0244(3) Uani 1 1 d D . . . .
H8A H 0.6191(15) 0.5988(15) 0.6851(18) 0.037 Uiso 1 1 d D U . . .
H8B H 0.571(2) 0.6158(16) 0.5353(17) 0.037 Uiso 1 1 d D U . . .
O9 O 0.12325(18) 0.77701(9) 0.4006(2) 0.0422(5) Uani 1 1 d D . . . .
H9A H 0.156(2) 0.7936(17) 0.4900(16) 0.063 Uiso 1 1 d D U . . .
H9B H 0.0594(18) 0.8007(17) 0.358(3) 0.063 Uiso 1 1 d D U . . .


_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
Cu O2 1.9553(12) . ?
Cu O4 2.0090(12) 4_545 ?
Cu O5 1.9548(13) . ?
Cu O6 1.9517(13) . ?
Cu O7 2.2432(13) . ?
C1 C1 1.406(3) 2_655 ?
C1 C2 1.389(2) . ?
C1 C4 1.508(2) . ?
C2 H2 0.950 . ?
C2 C3 1.397(2) . ?
C3 C3 1.407(3) 2_655 ?
C3 C5 1.505(2) . ?
C4 O1 1.242(2) . ?
C4 O2 1.271(2) . ?
C5 O3 1.250(2) . ?
C5 O4 1.276(2) . ?
O4 Cu 2.0090(12) 4 ?
O5 H5A 0.828(9) . ?
O5 H5B 0.827(9) . ?
O6 H6A 0.828(9) . ?
O6 H6B 0.829(9) . ?
O7 H7A 0.832(9) . ?
O7 H7B 0.843(9) . ?
O8 H8A 0.832(10) . ?
O8 H8B 0.832(9) . ?
O9 H9A 0.843(10) . ?
O9 H9B 0.838(10) . ?

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 Cu O4 175.22(5) . 4_545 ?
O2 Cu O5 86.44(6) . . ?
O2 Cu O6 91.15(6) . . ?
O2 Cu O7 92.90(5) . . ?
O4 Cu O5 88.90(5) 4_545 . ?
O4 Cu O6 93.60(6) 4_545 . ?
O4 Cu O7 86.48(5) 4_545 . ?
O5 Cu O6 173.57(6) . . ?
O5 Cu O7 95.36(5) . . ?
O6 Cu O7 90.71(5) . . ?
C1 C1 C2 119.43(10) 2_655 . ?
C1 C1 C4 121.03(9) 2_655 . ?
C2 C1 C4 119.48(15) . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.33(15) . . ?
H2 C2 C3 119.3 . . ?
C2 C3 C3 119.23(10) . 2_655 ?
C2 C3 C5 116.86(14) . . ?
C3 C3 C5 123.88(9) 2_655 . ?
C1 C4 O1 118.78(16) . . ?
C1 C4 O2 115.20(15) . . ?
O1 C4 O2 126.01(16) . . ?
C3 C5 O3 118.26(15) . . ?
C3 C5 O4 119.16(15) . . ?
O3 C5 O4 122.54(15) . . ?
Cu O2 C4 127.22(12) . . ?
Cu O4 C5 106.55(10) 4 . ?
Cu O5 H5A 119.3(15) . . ?
Cu O5 H5B 123.0(16) . . ?
H5A O5 H5B 110.1(15) . . ?
Cu O6 H6A 124.0(16) . . ?
Cu O6 H6B 121.2(16) . . ?
H6A O6 H6B 109.2(15) . . ?
Cu O7 H7A 100.8(16) . . ?
Cu O7 H7B 120.2(16) . . ?
H7A O7 H7B 107.1(14) . . ?
H8A O8 H8B 108.6(15) . . ?
H9A O9 H9B 106.7(16) . . ?

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
C1 C1 C2 C3 0.0(3) 2_655 . . . ?
C4 C1 C2 C3 -177.16(16) . . . . ?
C1 C2 C3 C3 -1.1(3) . . . 2_655 ?
C1 C2 C3 C5 177.16(15) . . . . ?
C1 C1 C4 O1 -51.5(3) 2_655 . . . ?
C1 C1 C4 O2 129.3(2) 2_655 . . . ?
C2 C1 C4 O1 125.59(19) . . . . ?
C2 C1 C4 O2 -53.6(2) . . . . ?
C2 C3 C5 O3 41.6(2) . . . . ?
C2 C3 C5 O4 -136.21(17) . . . . ?
C3 C3 C5 O3 -140.2(2) 2_655 . . . ?
C3 C3 C5 O4 42.0(3) 2_655 . . . ?
C1 C4 O2 Cu 177.49(11) . . . . ?
O1 C4 O2 Cu -1.6(3) . . . . ?
C3 C5 O4 Cu -173.10(12) . . . 4 ?
O3 C5 O4 Cu 9.19(19) . . . 4 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5A O1 0.828(9) 1.866(10) 2.6897(19) 173(2) 6_566
O5 H5B O8 0.827(9) 1.883(9) 2.701(2) 170(2) .
O6 H6A O4 0.828(9) 1.989(10) 2.8103(18) 172(2) 7_565
O6 H6B O7 0.829(9) 1.865(10) 2.6880(19) 172(3) 2
O7 H7A O3 0.832(9) 1.874(10) 2.6746(18) 161(2) 7_566
O7 H7B O9 0.843(9) 1.833(10) 2.674(2) 175(2) .
O8 H8A O3 0.832(10) 2.037(14) 2.816(2) 156(2) 8_566
O8 H8B O1 0.832(9) 1.995(12) 2.809(2) 166(3) 2_655
O9 H9A O2 0.843(10) 2.093(15) 2.893(2) 158(3) 7_566
O9 H9B O8 0.838(10) 2.22(2) 2.941(2) 145(2) 7_566

_refine_diff_density_max         0.519
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.072

_exptl_crystal_recrystallization_method 
'Obtained direct from slow diffusion synthesis'
####################################################################### 
# 
# 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_wc59
_database_code_depnum_ccdc_archive 'CCDC 1044118'
_audit_update_record             
;
2015-01-16 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 Cu O11,3 H2 O'
_chemical_formula_sum            'C10 H16 Cu O14'
_chemical_formula_weight         423.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.7846(4)
_cell_length_b                   10.9535(6)
_cell_length_c                   10.6835(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.810(2)
_cell_angle_gamma                90
_cell_volume                     793.55(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    6245
_cell_measurement_theta_min      2.664
_cell_measurement_theta_max      28.149

_exptl_crystal_description       Block
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_F_000             434
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.452
_shelx_estimated_absorpt_T_min   0.581
_shelx_estimated_absorpt_T_max   0.760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.580
_exptl_absorpt_correction_T_max  0.760
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART 1K CCD diffractometer'
_diffrn_measurement_method       'narrow-frame ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6540
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.859
_diffrn_reflns_theta_max         28.321
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3467
_reflns_number_gt                3379
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.992
_reflns_Friedel_fraction_max     0.936
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  SHELXL-2014/7
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0260P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.257(10)
_chemical_absolute_configuration .
_refine_ls_number_reflns         3467
_refine_ls_number_parameters     269
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0199
_refine_ls_R_factor_gt           0.0191
_refine_ls_wR_factor_ref         0.0488
_refine_ls_wR_factor_gt          0.0484
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Cu Cu 0.76183(5) 0.48926(2) 0.30815(4) 0.01561(8) Uani 1 1 d . . . . .
C1 C 0.7077(3) 0.8636(2) 0.2370(2) 0.0134(4) Uani 1 1 d . . . . .
C2 C 0.8577(3) 0.9305(2) 0.1811(2) 0.0132(4) Uani 1 1 d . . . . .
C3 C 0.8430(3) 1.0573(2) 0.1714(2) 0.0146(4) Uani 1 1 d . . . . .
H3 H 0.9441 1.1021 0.1326 0.018 Uiso 1 1 calc R U . . .
C4 C 0.6813(3) 1.1185(2) 0.2182(2) 0.0140(5) Uani 1 1 d . . . . .
C5 C 0.5331(3) 1.0519(2) 0.2758(2) 0.0135(4) Uani 1 1 d . . . . .
C6 C 0.5469(3) 0.9250(2) 0.2849(2) 0.0145(4) Uani 1 1 d . . . . .
H6 H 0.4460 0.8803 0.3241 0.017 Uiso 1 1 calc R U . . .
C7 C 0.7007(3) 0.7255(2) 0.2335(2) 0.0144(5) Uani 1 1 d . . . . .
C8 C 1.0337(3) 0.8664(2) 0.1317(2) 0.0157(4) Uani 1 1 d . . . . .
C9 C 0.6762(3) 1.2560(2) 0.2060(2) 0.0152(5) Uani 1 1 d . . . . .
C10 C 0.3608(3) 1.1166(2) 0.3287(2) 0.0157(4) Uani 1 1 d . . . . .
O1 O 0.6303(3) 0.67768(16) 0.13688(19) 0.0248(4) Uani 1 1 d . . . . .
O2 O 0.7600(3) 0.66650(14) 0.33000(17) 0.0181(4) Uani 1 1 d . . . . .
O3 O 1.0644(3) 0.75791(17) 0.1466(2) 0.0274(4) Uani 1 1 d . . . . .
O4 O 1.1519(3) 0.93993(16) 0.07205(18) 0.0221(4) Uani 1 1 d . . . . .
H4 H 1.245(5) 0.909(3) 0.048(3) 0.033 Uiso 1 1 d . U . . .
O5 O 0.5948(3) 1.30471(17) 0.11443(18) 0.0239(4) Uani 1 1 d . . . . .
O6 O 0.7698(3) 1.31239(14) 0.2955(2) 0.0186(4) Uani 1 1 d . . . . .
O7 O 0.3445(3) 1.22747(16) 0.3277(2) 0.0289(4) Uani 1 1 d . . . . .
O8 O 0.2284(3) 1.04273(17) 0.37434(19) 0.0221(4) Uani 1 1 d . . . . .
H8 H 0.144(6) 1.075(4) 0.400(3) 0.033 Uiso 1 1 d . U . . .
O9 O 0.9171(5) 0.48837(18) 0.4943(3) 0.0393(6) Uani 1 1 d D . . . .
H9A H 0.952(7) 0.5544(16) 0.528(4) 0.059 Uiso 1 1 d D U . . .
H9B H 0.971(6) 0.4326(19) 0.537(3) 0.059 Uiso 1 1 d D U . . .
O10 O 0.9907(4) 0.50110(16) 0.1973(3) 0.0265(5) Uani 1 1 d D . . . .
H10A H 1.022(6) 0.4396(16) 0.155(3) 0.040 Uiso 1 1 d D U . . .
H10B H 1.001(6) 0.5609(16) 0.150(2) 0.040 Uiso 1 1 d D U . . .
O11 O 0.4933(3) 0.4750(2) 0.3754(3) 0.0300(6) Uani 1 1 d D . . . .
H11A H 0.406(4) 0.529(2) 0.375(4) 0.045 Uiso 1 1 d D U . . .
H11B H 0.436(5) 0.4098(17) 0.357(4) 0.045 Uiso 1 1 d D U . . .
O12 O 1.1268(3) 0.29584(18) 0.08627(18) 0.0260(4) Uani 1 1 d D . . . .
H12A H 1.163(4) 0.293(3) 0.0122(13) 0.039 Uiso 1 1 d D U . . .
H12B H 1.228(3) 0.291(3) 0.132(2) 0.039 Uiso 1 1 d D U . . .
O13 O 0.2803(3) 0.68048(18) 0.37682(19) 0.0280(4) Uani 1 1 d D . . . .
H13A H 0.192(4) 0.687(3) 0.320(2) 0.042 Uiso 1 1 d D U . . .
H13B H 0.227(4) 0.693(3) 0.4453(16) 0.042 Uiso 1 1 d D U . . .
O14 O 1.4483(3) 0.82649(15) -0.02735(17) 0.0169(3) Uani 1 1 d D . . . .
H14A H 1.503(4) 0.779(2) 0.022(2) 0.025 Uiso 1 1 d D U . . .
H14B H 1.401(4) 0.791(2) -0.0887(19) 0.025 Uiso 1 1 d D U . . .


_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
Cu O2 1.9555(16) . ?
Cu O6 1.9430(15) 1_545 ?
Cu O9 2.220(3) . ?
Cu O10 1.986(2) . ?
Cu O11 1.985(2) . ?
C1 C2 1.403(3) . ?
C1 C6 1.393(3) . ?
C1 C7 1.513(3) . ?
C2 C3 1.396(3) . ?
C2 C8 1.495(3) . ?
C3 H3 0.950 . ?
C3 C4 1.392(3) . ?
C4 C5 1.401(3) . ?
C4 C9 1.512(3) . ?
C5 C6 1.396(3) . ?
C5 C10 1.493(3) . ?
C6 H6 0.950 . ?
C7 O1 1.240(3) . ?
C7 O2 1.271(3) . ?
C8 O3 1.216(3) . ?
C8 O4 1.315(3) . ?
C9 O5 1.230(3) . ?
C9 O6 1.288(3) . ?
C10 O7 1.219(3) . ?
C10 O8 1.315(3) . ?
O4 H4 0.77(4) . ?
O6 Cu 1.9430(15) 1_565 ?
O8 H8 0.73(4) . ?
O9 H9A 0.842(14) . ?
O9 H9B 0.839(14) . ?
O10 H10A 0.845(14) . ?
O10 H10B 0.833(14) . ?
O11 H11A 0.839(14) . ?
O11 H11B 0.834(14) . ?
O12 H12A 0.837(13) . ?
O12 H12B 0.835(13) . ?
O13 H13A 0.837(13) . ?
O13 H13B 0.838(13) . ?
O14 H14A 0.823(13) . ?
O14 H14B 0.821(13) . ?

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 Cu O6 176.91(11) . 1_545 ?
O2 Cu O9 84.38(8) . . ?
O2 Cu O10 90.82(8) . . ?
O2 Cu O11 91.46(9) . . ?
O6 Cu O9 92.55(9) 1_545 . ?
O6 Cu O10 89.98(8) 1_545 . ?
O6 Cu O11 88.55(10) 1_545 . ?
O9 Cu O10 100.16(12) . . ?
O9 Cu O11 95.19(12) . . ?
O10 Cu O11 164.64(10) . . ?
C2 C1 C6 119.4(2) . . ?
C2 C1 C7 122.3(2) . . ?
C6 C1 C7 117.87(19) . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 C8 120.2(2) . . ?
C3 C2 C8 119.8(2) . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(2) . . ?
H3 C3 C4 119.7 . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 C9 117.7(2) . . ?
C5 C4 C9 122.8(2) . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 C10 120.0(2) . . ?
C6 C5 C10 119.9(2) . . ?
C1 C6 C5 120.5(2) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C1 C7 O1 117.0(2) . . ?
C1 C7 O2 118.6(2) . . ?
O1 C7 O2 124.4(2) . . ?
C2 C8 O3 123.2(2) . . ?
C2 C8 O4 112.9(2) . . ?
O3 C8 O4 123.9(2) . . ?
C4 C9 O5 120.6(2) . . ?
C4 C9 O6 113.9(2) . . ?
O5 C9 O6 125.5(2) . . ?
C5 C10 O7 122.8(2) . . ?
C5 C10 O8 113.6(2) . . ?
O7 C10 O8 123.6(2) . . ?
Cu O2 C7 114.26(16) . . ?
C8 O4 H4 114(3) . . ?
Cu O6 C9 121.02(17) 1_565 . ?
C10 O8 H8 113(3) . . ?
Cu O9 H9A 120(2) . . ?
Cu O9 H9B 132(2) . . ?
H9A O9 H9B 106(2) . . ?
Cu O10 H10A 119(2) . . ?
Cu O10 H10B 120(2) . . ?
H10A O10 H10B 106(2) . . ?
Cu O11 H11A 127(3) . . ?
Cu O11 H11B 114(3) . . ?
H11A O11 H11B 106(2) . . ?
H12A O12 H12B 107(2) . . ?
H13A O13 H13B 107(2) . . ?
H14A O14 H14B 112(2) . . ?

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
C6 C1 C2 C3 -1.4(3) . . . . ?
C6 C1 C2 C8 178.6(2) . . . . ?
C7 C1 C2 C3 171.0(2) . . . . ?
C7 C1 C2 C8 -9.0(3) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C8 C2 C3 C4 -179.3(2) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C2 C3 C4 C9 179.21(19) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C3 C4 C5 C10 178.8(2) . . . . ?
C9 C4 C5 C6 -179.5(2) . . . . ?
C9 C4 C5 C10 -0.1(3) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C7 C1 C6 C5 -171.7(2) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C10 C5 C6 C1 -179.5(2) . . . . ?
C2 C1 C7 O1 -81.5(3) . . . . ?
C2 C1 C7 O2 100.8(3) . . . . ?
C6 C1 C7 O1 90.9(3) . . . . ?
C6 C1 C7 O2 -86.7(3) . . . . ?
C1 C2 C8 O3 -6.6(4) . . . . ?
C1 C2 C8 O4 174.1(2) . . . . ?
C3 C2 C8 O3 173.4(2) . . . . ?
C3 C2 C8 O4 -5.9(3) . . . . ?
C3 C4 C9 O5 92.0(3) . . . . ?
C3 C4 C9 O6 -85.3(3) . . . . ?
C5 C4 C9 O5 -89.2(3) . . . . ?
C5 C4 C9 O6 93.6(3) . . . . ?
C4 C5 C10 O7 -2.4(4) . . . . ?
C4 C5 C10 O8 176.8(2) . . . . ?
C6 C5 C10 O7 177.1(2) . . . . ?
C6 C5 C10 O8 -3.7(3) . . . . ?
C1 C7 O2 Cu -175.52(15) . . . . ?
O1 C7 O2 Cu 7.0(3) . . . . ?
C4 C9 O6 Cu -174.01(15) . . . 1_565 ?
O5 C9 O6 Cu 8.9(3) . . . 1_565 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O14 0.77(4) 1.86(4) 2.618(2) 173(4) .
O8 H8 O14 0.73(4) 1.90(4) 2.625(3) 173(4) 2_375
O9 H9A O5 0.842(14) 2.025(17) 2.853(3) 168(4) 2_575
O9 H9B O1 0.839(14) 1.922(16) 2.754(3) 171(4) 2_565
O10 H10A O12 0.845(14) 1.883(15) 2.718(3) 169(4) .
O10 H10B O3 0.833(14) 2.201(19) 2.911(3) 143(3) .
O11 H11A O13 0.839(14) 1.864(15) 2.675(3) 162(3) .
O11 H11B O7 0.834(14) 2.112(14) 2.932(3) 168(3) 1_545
O12 H12A O2 0.837(13) 2.120(16) 2.939(3) 166(4) 2_564
O12 H12B O5 0.835(13) 2.50(2) 3.181(3) 139(3) 1_645
O12 H12B O7 0.835(13) 2.32(2) 3.026(3) 143(3) 1_645
O13 H13A O3 0.837(13) 2.169(19) 2.948(3) 155(3) 1_455
O13 H13B O5 0.838(13) 2.043(15) 2.873(3) 171(4) 2_475
O14 H14A O1 0.823(13) 1.846(13) 2.669(3) 178(3) 1_655
O14 H14B O6 0.821(13) 1.878(16) 2.687(3) 168(3) 2_574

_refine_diff_density_max         0.409
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.058

_exptl_crystal_recrystallization_method 
'Obtained direct from slow diffusion synthesis'
####################################################################### 
# 
# 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_kw23
_database_code_depnum_ccdc_archive 'CCDC 1044119'
_audit_update_record             
;
2015-01-16 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H2 O8 Cu K2,4 H2 O'
_chemical_formula_sum            'C10 H10 Cu K2 O12'
_chemical_formula_weight         463.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7391(15)
_cell_length_b                   10.6004(19)
_cell_length_c                   10.6159(19)
_cell_angle_alpha                112.867(10)
_cell_angle_beta                 90.411(13)
_cell_angle_gamma                104.192(10)
_cell_volume                     772.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    32
_cell_measurement_theta_min      10.0
_cell_measurement_theta_max      12.5

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.994
_exptl_crystal_F_000             466
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    2.016
_shelx_estimated_absorpt_T_min   0.378
_shelx_estimated_absorpt_T_max   0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.62
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_process_details   SHELXTL
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Stoe-Siemens four-circle diffractometer'
_diffrn_measurement_method       'ω/θ scans with on-line profile fitting'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5452
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.096
_diffrn_reflns_theta_max         24.982
_diffrn_reflns_theta_full        24.982
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2726
_reflns_number_gt                2383
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Stoe DIF4'
_computing_cell_refinement       'Stoe DIF4'
_computing_data_reduction        'local programs'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  SHELXL-2014/7
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_refine_special_details          
'No H atoms found on water O12, possibly partial occupany/disordered'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0457P)²+0.7234P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2726
_refine_ls_number_parameters     253
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0837
_refine_ls_wR_factor_gt          0.0789
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Cu Cu 0.50268(4) 0.23363(3) 0.76455(3) 0.01668(12) Uani 1 1 d . . . . .
K1 K 0.82029(10) 0.19096(7) 0.49184(7) 0.03570(18) Uani 1 1 d . . . . .
K2 K 0.80028(11) 0.51691(8) 0.14863(7) 0.0412(2) Uani 1 1 d . . . . .
C1 C 0.3343(3) 0.2414(3) 0.3963(2) 0.0170(5) Uani 1 1 d . . . . .
C2 C 0.3886(3) 0.1380(3) 0.2879(3) 0.0168(5) Uani 1 1 d . . . . .
C3 C 0.4133(4) 0.1544(3) 0.1651(3) 0.0203(5) Uani 1 1 d . . . . .
H3 H 0.4512 0.0864 0.0934 0.024 Uiso 1 1 calc R U . . .
C4 C 0.3826(4) 0.2701(3) 0.1475(3) 0.0182(5) Uani 1 1 d . . . . .
C5 C 0.3275(4) 0.3735(3) 0.2553(3) 0.0177(5) Uani 1 1 d . . . . .
C6 C 0.3035(4) 0.3577(3) 0.3789(3) 0.0187(5) Uani 1 1 d . . . . .
H6 H 0.2663 0.4260 0.4508 0.022 Uiso 1 1 calc R U . . .
C7 C 0.3227(4) 0.2355(3) 0.5358(3) 0.0200(5) Uani 1 1 d . . . . .
C8 C 0.4038(4) 0.0008(3) 0.2930(2) 0.0190(5) Uani 1 1 d . . . . .
C9 C 0.3981(4) 0.2730(3) 0.0071(3) 0.0191(5) Uani 1 1 d . . . . .
C10 C 0.3091(4) 0.5083(3) 0.2463(3) 0.0216(6) Uani 1 1 d . . . . .
O1 O 0.2030(3) 0.2735(2) 0.6053(2) 0.0303(5) Uani 1 1 d . . . . .
O2 O 0.4480(3) 0.1924(2) 0.57214(18) 0.0271(4) Uani 1 1 d . . . . .
O3 O 0.2667(3) -0.0833(2) 0.3040(2) 0.0299(5) Uani 1 1 d . . . . .
O4 O 0.5536(3) -0.02732(19) 0.27529(19) 0.0222(4) Uani 1 1 d . . . . .
O5 O 0.5481(3) 0.2678(2) -0.03986(18) 0.0238(4) Uani 1 1 d . . . . .
O6 O 0.2663(3) 0.2726(2) -0.0597(2) 0.0318(5) Uani 1 1 d . . . . .
O7 O 0.4337(3) 0.5628(2) 0.1894(2) 0.0284(5) Uani 1 1 d . . . . .
O8 O 0.1861(3) 0.5593(2) 0.2976(2) 0.0316(5) Uani 1 1 d . . . . .
O9 O 0.8641(4) 0.3601(4) 0.3236(4) 0.0687(9) Uani 1 1 d DG . . . .
H9A H 0.963(4) 0.422(4) 0.341(5) 0.103 Uiso 1 1 d D U . . .
H9B H 0.866(7) 0.294(4) 0.248(3) 0.103 Uiso 1 1 d D U . . .
O10 O 0.9477(4) -0.0132(4) 0.3075(4) 0.0856(12) Uani 1 1 d DG . . . .
H10A H 0.946(8) 0.021(7) 0.247(6) 0.128 Uiso 1 1 d D U . . .
H10B H 1.048(4) -0.032(7) 0.306(6) 0.128 Uiso 1 1 d D U . . .
O11 O 0.9407(5) 0.3187(4) -0.0308(5) 0.0994(15) Uani 1 1 d DG . . . .
H11A H 1.046(4) 0.309(8) -0.039(7) 0.149 Uiso 1 1 d D U . . .
H11B H 0.897(9) 0.267(7) 0.014(8) 0.149 Uiso 1 1 d D U . . .
O12 O 0.8887(10) 0.0893(8) 0.1143(7) 0.186(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu O2 1.9354(18) . ?
Cu O4 1.9907(18) 2_656 ?
Cu O5 1.9771(18) 1_556 ?
Cu O7 1.9476(19) 2_666 ?
K1 O1 2.975(2) 1_655 ?
K1 O2 3.013(2) . ?
K1 O3 2.832(2) 2_656 ?
K1 O4 2.890(2) . ?
K1 O8 2.734(2) 2_666 ?
K1 O9 2.952(3) . ?
K1 O10 2.696(3) . ?
K2 O1 2.698(2) 2_666 ?
K2 O5 2.846(2) . ?
K2 O6 2.885(2) 2_665 ?
K2 O7 3.001(2) . ?
K2 O8 3.216(2) 1_655 ?
K2 O9 3.041(4) . ?
K2 O11 2.695(4) . ?
K2 O11 2.939(5) 2_765 ?
C1 C2 1.398(3) . ?
C1 C6 1.390(4) . ?
C1 C7 1.509(3) . ?
C2 C3 1.389(4) . ?
C2 C8 1.510(3) . ?
C3 H3 0.930 . ?
C3 C4 1.384(4) . ?
C4 C5 1.398(4) . ?
C4 C9 1.509(3) . ?
C5 C6 1.395(4) . ?
C5 C10 1.509(3) . ?
C6 H6 0.930 . ?
C7 O1 1.235(3) . ?
C7 O2 1.283(3) . ?
C8 O3 1.246(3) . ?
C8 O4 1.264(3) . ?
C9 O5 1.271(3) . ?
C9 O6 1.237(3) . ?
C10 O7 1.279(3) . ?
C10 O8 1.235(3) . ?
O1 K1 2.975(2) 1_455 ?
O1 K2 2.698(2) 2_666 ?
O3 K1 2.832(2) 2_656 ?
O4 Cu 1.9906(18) 2_656 ?
O5 Cu 1.9771(18) 1_554 ?
O6 K2 2.885(2) 2_665 ?
O7 Cu 1.9477(19) 2_666 ?
O8 K1 2.734(2) 2_666 ?
O8 K2 3.216(2) 1_455 ?
O9 H9A 0.842(10) . ?
O9 H9B 0.837(10) . ?
O10 H10A 0.847(10) . ?
O10 H10B 0.845(10) . ?
O11 K2 2.939(5) 2_765 ?
O11 H11A 0.850(10) . ?
O11 H11B 0.863(10) . ?

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 Cu O4 91.27(8) . 2_656 ?
O2 Cu O5 177.13(8) . 1_556 ?
O2 Cu O7 91.03(8) . 2_666 ?
O4 Cu O5 86.56(8) 2_656 1_556 ?
O4 Cu O7 177.28(8) 2_656 2_666 ?
O5 Cu O7 91.19(8) 1_556 2_666 ?
O1 K1 O2 143.23(6) 1_655 . ?
O1 K1 O3 87.65(6) 1_655 2_656 ?
O1 K1 O4 142.84(6) 1_655 . ?
O1 K1 O8 83.62(7) 1_655 2_666 ?
O1 K1 O9 97.52(8) 1_655 . ?
O1 K1 O10 77.46(9) 1_655 . ?
O2 K1 O3 66.66(6) . 2_656 ?
O2 K1 O4 69.36(6) . . ?
O2 K1 O8 67.78(6) . 2_666 ?
O2 K1 O9 101.86(8) . . ?
O2 K1 O10 131.60(8) . . ?
O3 K1 O4 96.74(6) 2_656 . ?
O3 K1 O8 82.19(6) 2_656 2_666 ?
O3 K1 O9 164.83(8) 2_656 . ?
O3 K1 O10 101.99(11) 2_656 . ?
O4 K1 O8 133.54(6) . 2_666 ?
O4 K1 O9 87.77(8) . . ?
O4 K1 O10 65.51(8) . . ?
O8 K1 O9 84.21(9) 2_666 . ?
O8 K1 O10 160.37(9) 2_666 . ?
O9 K1 O10 93.07(12) . . ?
O1 K2 O5 136.33(7) 2_666 . ?
O1 K2 O6 79.96(6) 2_666 2_665 ?
O1 K2 O7 68.11(6) 2_666 . ?
O1 K2 O8 79.68(6) 2_666 1_655 ?
O1 K2 O9 83.39(8) 2_666 . ?
O1 K2 O11 153.73(10) 2_666 . ?
O1 K2 O11 99.12(9) 2_666 2_765 ?
O5 K2 O6 100.66(6) . 2_665 ?
O5 K2 O7 72.49(6) . . ?
O5 K2 O8 130.92(6) . 1_655 ?
O5 K2 O9 90.79(8) . . ?
O5 K2 O11 64.20(9) . . ?
O5 K2 O11 117.00(9) . 2_765 ?
O6 K2 O7 65.89(6) 2_665 . ?
O6 K2 O8 121.05(6) 2_665 1_655 ?
O6 K2 O9 163.33(8) 2_665 . ?
O6 K2 O11 116.16(12) 2_665 . ?
O6 K2 O11 54.77(8) 2_665 2_765 ?
O7 K2 O8 145.61(6) . 1_655 ?
O7 K2 O9 106.92(7) . . ?
O7 K2 O11 136.34(9) . . ?
O7 K2 O11 120.65(8) . 2_765 ?
O8 K2 O9 55.92(7) 1_655 . ?
O8 K2 O11 74.21(9) 1_655 . ?
O8 K2 O11 75.01(9) 1_655 2_765 ?
O9 K2 O11 79.69(13) . . ?
O9 K2 O11 129.74(10) . 2_765 ?
O11 K2 O11 77.06(14) . 2_765 ?
C2 C1 C6 119.5(2) . . ?
C2 C1 C7 121.3(2) . . ?
C6 C1 C7 119.0(2) . . ?
C1 C2 C3 119.4(2) . . ?
C1 C2 C8 122.5(2) . . ?
C3 C2 C8 117.8(2) . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.1(2) . . ?
H3 C3 C4 119.4 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 C9 117.5(2) . . ?
C5 C4 C9 122.6(2) . . ?
C4 C5 C6 119.2(2) . . ?
C4 C5 C10 121.9(2) . . ?
C6 C5 C10 118.7(2) . . ?
C1 C6 C5 120.9(2) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C1 C7 O1 120.3(2) . . ?
C1 C7 O2 113.8(2) . . ?
O1 C7 O2 125.9(2) . . ?
C2 C8 O3 119.0(2) . . ?
C2 C8 O4 117.5(2) . . ?
O3 C8 O4 123.3(2) . . ?
C4 C9 O5 116.6(2) . . ?
C4 C9 O6 120.2(2) . . ?
O5 C9 O6 123.0(2) . . ?
C5 C10 O7 114.0(2) . . ?
C5 C10 O8 119.8(2) . . ?
O7 C10 O8 126.1(2) . . ?
K1 O1 K2 100.21(7) 1_455 2_666 ?
K1 O1 C7 123.81(17) 1_455 . ?
K2 O1 C7 134.21(19) 2_666 . ?
Cu O2 K1 97.07(8) . . ?
Cu O2 C7 119.53(16) . . ?
K1 O2 C7 133.23(16) . . ?
K1 O3 C8 132.00(18) 2_656 . ?
Cu O4 K1 124.16(8) 2_656 . ?
Cu O4 C8 104.03(16) 2_656 . ?
K1 O4 C8 108.90(15) . . ?
Cu O5 K2 121.61(8) 1_554 . ?
Cu O5 C9 104.89(16) 1_554 . ?
K2 O5 C9 105.08(15) . . ?
K2 O6 C9 131.14(18) 2_665 . ?
Cu O7 K2 98.46(8) 2_666 . ?
Cu O7 C10 119.92(17) 2_666 . ?
K2 O7 C10 129.24(17) . . ?
K1 O8 K2 93.78(6) 2_666 1_455 ?
K1 O8 C10 133.05(19) 2_666 . ?
K2 O8 C10 128.21(18) 1_455 . ?
K1 O9 K2 164.59(12) . . ?
K1 O9 H9A 115(4) . . ?
K1 O9 H9B 97(4) . . ?
K2 O9 H9A 79(4) . . ?
K2 O9 H9B 84(4) . . ?
H9A O9 H9B 107.0(17) . . ?
K1 O10 H10A 92(5) . . ?
K1 O10 H10B 132(5) . . ?
H10A O10 H10B 105.6(17) . . ?
K2 O11 K2 102.94(14) . 2_765 ?
K2 O11 H11A 134(5) . . ?
K2 O11 H11A 59(4) 2_765 . ?
K2 O11 H11B 86(5) . . ?
K2 O11 H11B 161(5) 2_765 . ?
H11A O11 H11B 103.2(16) . . ?

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
C6 C1 C2 C3 0.9(4) . . . . ?
C6 C1 C2 C8 -172.7(3) . . . . ?
C7 C1 C2 C3 -174.1(3) . . . . ?
C7 C1 C2 C8 12.3(4) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C8 C2 C3 C4 173.0(3) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C2 C3 C4 C9 -175.1(3) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C3 C4 C5 C10 174.1(3) . . . . ?
C9 C4 C5 C6 175.2(2) . . . . ?
C9 C4 C5 C10 -10.4(4) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
C7 C1 C6 C5 174.5(2) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C10 C5 C6 C1 -174.3(2) . . . . ?
C2 C1 C7 O1 -144.2(3) . . . . ?
C2 C1 C7 O2 37.5(3) . . . . ?
C6 C1 C7 O1 40.8(4) . . . . ?
C6 C1 C7 O2 -137.5(3) . . . . ?
C1 C2 C8 O3 61.7(4) . . . . ?
C1 C2 C8 O4 -123.5(3) . . . . ?
C3 C2 C8 O3 -112.0(3) . . . . ?
C3 C2 C8 O4 62.7(3) . . . . ?
C3 C4 C9 O5 -58.3(3) . . . . ?
C3 C4 C9 O6 117.9(3) . . . . ?
C5 C4 C9 O5 126.1(3) . . . . ?
C5 C4 C9 O6 -57.7(4) . . . . ?
C4 C5 C10 O7 -40.1(4) . . . . ?
C4 C5 C10 O8 143.2(3) . . . . ?
C6 C5 C10 O7 134.3(3) . . . . ?
C6 C5 C10 O8 -42.4(4) . . . . ?
C1 C7 O1 K1 44.8(3) . . . 1_455 ?
C1 C7 O1 K2 -116.8(2) . . . 2_666 ?
O2 C7 O1 K1 -137.1(2) . . . 1_455 ?
O2 C7 O1 K2 61.3(4) . . . 2_666 ?
C1 C7 O2 Cu 160.45(17) . . . . ?
C1 C7 O2 K1 23.9(3) . . . . ?
O1 C7 O2 Cu -17.8(4) . . . . ?
O1 C7 O2 K1 -154.4(2) . . . . ?
C2 C8 O3 K1 -119.2(2) . . . 2_656 ?
O4 C8 O3 K1 66.4(3) . . . 2_656 ?
C2 C8 O4 Cu -164.06(18) . . . 2_656 ?
C2 C8 O4 K1 61.7(2) . . . . ?
O3 C8 O4 Cu 10.5(3) . . . 2_656 ?
O3 C8 O4 K1 -123.7(2) . . . . ?
C4 C9 O5 Cu 168.62(17) . . . 1_554 ?
C4 C9 O5 K2 -62.1(2) . . . . ?
O6 C9 O5 Cu -7.4(3) . . . 1_554 ?
O6 C9 O5 K2 121.9(2) . . . . ?
C4 C9 O6 K2 115.3(2) . . . 2_665 ?
O5 C9 O6 K2 -68.7(3) . . . 2_665 ?
C5 C10 O7 Cu -153.55(18) . . . 2_666 ?
C5 C10 O7 K2 -20.0(3) . . . . ?
O8 C10 O7 Cu 23.0(4) . . . 2_666 ?
O8 C10 O7 K2 156.5(2) . . . . ?
C5 C10 O8 K1 116.0(2) . . . 2_666 ?
C5 C10 O8 K2 -95.7(3) . . . 1_455 ?
O7 C10 O8 K1 -60.3(4) . . . 2_666 ?
O7 C10 O8 K2 88.0(3) . . . 1_455 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O9 H9A O8 0.842(10) 2.15(3) 2.938(4) 156(5) 1_655
O9 H9B O12 0.837(10) 2.14(3) 2.921(8) 156(6) .
O10 H10A O12 0.847(10) 1.915(16) 2.750(9) 168(6) .
O10 H10B O3 0.845(10) 1.899(11) 2.744(4) 177(6) 1_655
O11 H11A O6 0.850(10) 1.832(13) 2.680(4) 175(7) 1_655
O11 H11B O12 0.863(10) 2.49(3) 3.299(9) 156(6) .

_refine_diff_density_max         0.717
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.077

_exptl_crystal_recrystallization_method 
'Obtained direct from slow diffusion synthesis'
####################################################################### 
# 
# 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_wc37
_database_code_depnum_ccdc_archive 'CCDC 1044120'
_audit_update_record             
;
2015-01-16 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H2 Cu Na2 O8,4 H2 O'
_chemical_formula_sum            'C10 H10 Cu Na2 O12'
_chemical_formula_weight         431.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.8940(5)
_cell_length_b                   16.3377(11)
_cell_length_c                   12.9381(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.666(2)
_cell_angle_gamma                90
_cell_volume                     1436.56(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    6028
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      28.54

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.996
_exptl_crystal_F_000             868
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.649
_shelx_estimated_absorpt_T_min   0.558
_shelx_estimated_absorpt_T_max   0.852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker SMART 1K diffractometer'
_diffrn_measurement_method       'narrow-frame ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6058
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.493
_diffrn_reflns_theta_max         28.543
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1732
_reflns_number_gt                1710
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  SHELXL-2014/7
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL and local programs'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0258P)²+1.6844P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1732
_refine_ls_number_parameters     130
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0208
_refine_ls_R_factor_gt           0.0205
_refine_ls_wR_factor_ref         0.0565
_refine_ls_wR_factor_gt          0.0564
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_restrained_S_all      1.157
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Cu Cu 0.5000 0.51222(2) 0.7500 0.00760(8) Uani 1 2 d S T P . .
Na Na 0.82351(8) 0.40012(3) 0.63321(4) 0.01423(13) Uani 1 1 d . . . . .
C1 C 0.70390(19) 0.67631(8) 0.54458(10) 0.0094(2) Uani 1 1 d . . . . .
C2 C 0.72402(18) 0.67889(7) 0.43951(10) 0.0091(2) Uani 1 1 d . . . . .
C3 C 0.76957(19) 0.75261(8) 0.39555(10) 0.0105(2) Uani 1 1 d . . . . .
H3 H 0.7827 0.7545 0.3237 0.013 Uiso 1 1 calc R U . . .
C4 C 0.6727(2) 0.59790(8) 0.60006(10) 0.0101(2) Uani 1 1 d . . . . .
C5 C 0.69376(19) 0.60605(7) 0.36820(10) 0.0092(2) Uani 1 1 d . . . . .
O1 O 0.78567(16) 0.54037(6) 0.59587(9) 0.0176(2) Uani 1 1 d . . . . .
O2 O 0.53142(15) 0.59977(6) 0.65290(8) 0.0127(2) Uani 1 1 d . . . . .
O3 O 0.82406(15) 0.58551(6) 0.31828(8) 0.0133(2) Uani 1 1 d . . . . .
O4 O 0.52703(14) 0.57080(6) 0.36032(8) 0.01179(19) Uani 1 1 d . . . . .
O5 O 0.86811(16) 0.39613(7) 0.45692(9) 0.0189(2) Uani 1 1 d D . . . .
H5A H 0.7640(18) 0.4152(13) 0.4253(17) 0.037(6) Uiso 1 1 d D . . . .
H5B H 0.962(2) 0.4206(14) 0.4393(19) 0.045(7) Uiso 1 1 d D . . . .
O6 O 0.77637(18) 0.25673(7) 0.63646(10) 0.0225(2) Uani 1 1 d D . . . .
H6A H 0.869(3) 0.2232(13) 0.651(2) 0.058(9) Uiso 1 1 d D . . . .
H6B H 0.682(3) 0.2302(14) 0.602(2) 0.060(9) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu O2 1.9397(10) . ?
Cu O2 1.9397(10) 2_656 ?
Cu O4 1.9551(9) 5_666 ?
Cu O4 1.9551(9) 6_566 ?
Na O1 2.3472(11) . ?
Na O5 2.3531(13) . ?
Na O6 2.3665(13) . ?
Na O3 2.4053(11) 6_566 ?
Na O3 2.4166(12) 5_766 ?
Na O4 2.4780(11) 5_666 ?
Na H5A 2.66(2) . ?
C1 C2 1.3901(18) . ?
C1 C3 1.3908(17) 7_666 ?
C1 C4 1.5016(17) . ?
C2 C3 1.3903(17) . ?
C2 C5 1.4988(17) . ?
C3 C1 1.3908(17) 7_666 ?
C3 H3 0.9500 . ?
C4 O1 1.2277(17) . ?
C4 O2 1.2808(17) . ?
C5 O3 1.2375(16) . ?
C5 O4 1.2743(16) . ?
O3 Na 2.4052(11) 6_565 ?
O3 Na 2.4166(12) 5_766 ?
O4 Cu 1.9551(9) 5_666 ?
O4 Na 2.4780(11) 5_666 ?
O5 H5A 0.826(9) . ?
O5 H5B 0.825(9) . ?
O6 H6A 0.840(10) . ?
O6 H6B 0.841(10) . ?

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 Cu O2 84.98(6) . 2_656 ?
O2 Cu O4 92.64(4) . 5_666 ?
O2 Cu O4 167.72(4) 2_656 5_666 ?
O2 Cu O4 167.72(4) . 6_566 ?
O2 Cu O4 92.64(4) 2_656 6_566 ?
O4 Cu O4 92.14(6) 5_666 6_566 ?
O1 Na O5 81.70(4) . . ?
O1 Na O6 163.58(5) . . ?
O5 Na O6 91.74(4) . . ?
O1 Na O3 95.23(4) . 6_566 ?
O5 Na O3 171.51(5) . 6_566 ?
O6 Na O3 93.22(4) . 6_566 ?
O1 Na O3 91.76(4) . 5_766 ?
O5 Na O3 88.00(4) . 5_766 ?
O6 Na O3 103.10(4) . 5_766 ?
O3 Na O3 84.18(4) 6_566 5_766 ?
O1 Na O4 75.20(4) . 5_666 ?
O5 Na O4 108.96(4) . 5_666 ?
O6 Na O4 92.96(4) . 5_666 ?
O3 Na O4 77.66(4) 6_566 5_666 ?
O3 Na O4 156.39(4) 5_766 5_666 ?
O1 Na H5A 73.1(5) . . ?
O5 Na H5A 17.6(3) . . ?
O6 Na H5A 96.4(5) . . ?
O3 Na H5A 166.1(4) 6_566 . ?
O3 Na H5A 103.4(3) 5_766 . ?
O4 Na H5A 91.8(3) 5_666 . ?
C2 C1 C3 119.60(12) . 7_666 ?
C2 C1 C4 122.62(11) . . ?
C3 C1 C4 117.53(12) 7_666 . ?
C1 C2 C3 119.52(12) . . ?
C1 C2 C5 123.47(11) . . ?
C3 C2 C5 116.98(11) . . ?
C2 C3 C1 120.87(12) . 7_666 ?
C2 C3 H3 119.6 . . ?
C1 C3 H3 119.6 7_666 . ?
O1 C4 O2 125.93(12) . . ?
O1 C4 C1 119.28(12) . . ?
O2 C4 C1 114.69(11) . . ?
O3 C5 O4 124.04(12) . . ?
O3 C5 C2 119.89(12) . . ?
O4 C5 C2 116.01(11) . . ?
C4 O1 Na 141.96(9) . . ?
C4 O2 Cu 120.38(9) . . ?
C5 O3 Na 127.82(9) . 6_565 ?
C5 O3 Na 128.64(9) . 5_766 ?
Na O3 Na 94.73(4) 6_565 5_766 ?
C5 O4 Cu 110.24(8) . 5_666 ?
C5 O4 Na 141.48(8) . 5_666 ?
Cu O4 Na 100.59(4) 5_666 5_666 ?
Na O5 H5A 103.0(16) . . ?
Na O5 H5B 119.4(18) . . ?
H5A O5 H5B 109.7(15) . . ?
Na O6 H6A 123.2(18) . . ?
Na O6 H6B 126.6(18) . . ?
H6A O6 H6B 105.7(15) . . ?

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
C3 C1 C2 C3 -0.3(2) 7_666 . . . ?
C4 C1 C2 C3 -174.44(12) . . . . ?
C3 C1 C2 C5 -178.55(12) 7_666 . . . ?
C4 C1 C2 C5 7.3(2) . . . . ?
C1 C2 C3 C1 0.3(2) . . . 7_666 ?
C5 C2 C3 C1 178.67(12) . . . 7_666 ?
C2 C1 C4 O1 52.03(19) . . . . ?
C3 C1 C4 O1 -122.24(14) 7_666 . . . ?
C2 C1 C4 O2 -131.38(13) . . . . ?
C3 C1 C4 O2 54.35(16) 7_666 . . . ?
C1 C2 C5 O3 -126.26(14) . . . . ?
C3 C2 C5 O3 55.43(17) . . . . ?
C1 C2 C5 O4 56.47(17) . . . . ?
C3 C2 C5 O4 -121.84(13) . . . . ?
O2 C4 O1 Na 15.6(2) . . . . ?
C1 C4 O1 Na -168.25(11) . . . . ?
O1 C4 O2 Cu 7.84(19) . . . . ?
C1 C4 O2 Cu -168.49(8) . . . . ?
O4 C5 O3 Na 69.48(16) . . . 6_565 ?
C2 C5 O3 Na -107.56(12) . . . 6_565 ?
O4 C5 O3 Na -151.57(10) . . . 5_766 ?
C2 C5 O3 Na 31.39(17) . . . 5_766 ?
O3 C5 O4 Cu -5.20(16) . . . 5_666 ?
C2 C5 O4 Cu 171.94(8) . . . 5_666 ?
O3 C5 O4 Na -146.24(11) . . . 5_666 ?
C2 C5 O4 Na 30.90(19) . . . 5_666 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5A O2 0.826(9) 2.130(13) 2.8802(15) 151(2) 5_666
O5 H5B O1 0.825(9) 1.976(10) 2.7905(15) 169(2) 5_766
O6 H6A O2 0.840(10) 2.303(14) 3.0963(15) 158(2) 3_545
O6 H6B O5 0.841(10) 2.21(2) 2.8782(16) 137(2) 7_656

_refine_diff_density_max         0.431
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.071

_exptl_crystal_recrystallization_method 
'Obtained direct from slow diffusion synthesis'
####################################################################### 
# 
# 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_wc1
_database_code_depnum_ccdc_archive 'CCDC 1044121'
_audit_update_record             
;
2015-01-16 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '4 C6 H16 N +,C24 H16 Cu2 O18 4-'
_chemical_formula_sum            'C48 H80 Cu2 N4 O18'
_chemical_formula_weight         1128.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.3114(10)
_cell_length_b                   11.5464(10)
_cell_length_c                   11.7074(11)
_cell_angle_alpha                80.130(2)
_cell_angle_beta                 66.441(2)
_cell_angle_gamma                71.052(2)
_cell_volume                     1324.1(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    4477
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      28.71

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_F_000             598
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.878
_shelx_estimated_absorpt_T_min   0.720
_shelx_estimated_absorpt_T_max   0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.720
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART CCD diffractometer'
_diffrn_measurement_method       'narrow-frame ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7999
_diffrn_reflns_av_unetI/netI     0.1036
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.867
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             4562
_reflns_number_gt                3103
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'local programs'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  SHELXL-2014/7
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL and local programs'
_refine_special_details          
'Disorder resolved in one cation and coordinated ethanol'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1174P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4562
_refine_ls_number_parameters     362
_refine_ls_number_restraints     512
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.0735
_refine_ls_wR_factor_ref         0.1927
_refine_ls_wR_factor_gt          0.1753
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.980
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Cu Cu 0.37128(7) 0.78960(6) 0.63060(6) 0.0179(2) Uani 1 1 d . U . . .
C1 C 0.6217(5) 0.5632(5) 0.6089(5) 0.0171(11) Uani 1 1 d . U . . .
C2 C 0.6571(5) 0.6183(4) 0.4883(5) 0.0159(11) Uani 1 1 d . U . . .
C3 C 0.7229(5) 0.5431(5) 0.3864(5) 0.0169(12) Uani 1 1 d . U . . .
H3 H 0.7521 0.5801 0.3048 0.020 Uiso 1 1 calc R U . . .
C4 C 0.7474(5) 0.4164(5) 0.3995(5) 0.0167(11) Uani 1 1 d . U . . .
C5 C 0.7096(5) 0.3627(4) 0.5203(5) 0.0164(11) Uani 1 1 d . U . . .
C6 C 0.6518(6) 0.4365(5) 0.6214(5) 0.0186(12) Uani 1 1 d . U . . .
H6 H 0.6318 0.3985 0.7029 0.022 Uiso 1 1 calc R U . . .
C7 C 0.5630(5) 0.6307(5) 0.7300(5) 0.0169(11) Uani 1 1 d . U . . .
C8 C 0.6402(6) 0.7561(5) 0.4552(5) 0.0185(12) Uani 1 1 d . U . . .
C9 C 0.8232(6) 0.3477(5) 0.2792(5) 0.0187(12) Uani 1 1 d . U . . .
C10 C 0.7376(6) 0.2256(5) 0.5503(5) 0.0183(12) Uani 1 1 d . U . . .
O1 O 0.6094(4) 0.5830(3) 0.8115(4) 0.0310(10) Uani 1 1 d . U . . .
O2 O 0.4682(4) 0.7293(3) 0.7430(3) 0.0209(9) Uani 1 1 d . U . . .
O3 O 0.7396(4) 0.7851(3) 0.3770(4) 0.0274(10) Uani 1 1 d . U . . .
O4 O 0.5272(4) 0.8312(3) 0.5067(4) 0.0236(9) Uani 1 1 d . U . . .
O5 O 0.9294(4) 0.3691(4) 0.2089(4) 0.0295(10) Uani 1 1 d . U . . .
O6 O 0.7720(4) 0.2758(3) 0.2545(3) 0.0214(9) Uani 1 1 d . U . . .
O7 O 0.7729(4) 0.1843(3) 0.6407(4) 0.0294(10) Uani 1 1 d . U . . .
O8 O 0.7213(4) 0.1578(3) 0.4862(3) 0.0237(9) Uani 1 1 d . U . . .
O9 O 0.2787(4) 0.9777(3) 0.7133(4) 0.0291(10) Uani 1 1 d D U . . .
H9 H 0.281(7) 1.043(3) 0.670(5) 0.044 Uiso 1 1 d D U . . .
C11 C 0.1579(8) 1.0063(6) 0.8158(7) 0.057(2) Uani 1 1 d D U . . .
H11A H 0.1453 1.0850 0.8481 0.068 Uiso 0.606(14) 1 calc R U P A 1
H11B H 0.1611 0.9417 0.8830 0.068 Uiso 0.606(14) 1 calc R U P A 1
H11C H 0.1378 0.9291 0.8581 0.068 Uiso 0.394(14) 1 calc R U P A 2
H11D H 0.0845 1.0530 0.7858 0.068 Uiso 0.394(14) 1 calc R U P A 2
C12 C 0.0458(14) 1.0157(12) 0.7806(15) 0.077(4) Uani 0.606(14) 1 d D U P A 1
H12A H -0.0382 1.0357 0.8534 0.116 Uiso 0.606(14) 1 calc R U P A 1
H12B H 0.0420 1.0804 0.7148 0.116 Uiso 0.606(14) 1 calc R U P A 1
H12C H 0.0578 0.9373 0.7497 0.116 Uiso 0.606(14) 1 calc R U P A 1
C12X C 0.160(2) 1.0773(19) 0.9052(18) 0.074(6) Uani 0.394(14) 1 d D U P A 2
H12D H 0.0727 1.0944 0.9746 0.110 Uiso 0.394(14) 1 calc R U P A 2
H12E H 0.2309 1.0309 0.9370 0.110 Uiso 0.394(14) 1 calc R U P A 2
H12F H 0.1775 1.1548 0.8646 0.110 Uiso 0.394(14) 1 calc R U P A 2
N1 N 0.8030(5) 0.4069(4) 0.8869(4) 0.0237(11) Uani 1 1 d . U . . .
H1 H 0.7288 0.4652 0.8623 0.028 Uiso 1 1 calc R U . . .
C13 C 0.9168(6) 0.3541(6) 0.7713(5) 0.0315(14) Uani 1 1 d . U . . .
H13A H 0.8927 0.2934 0.7407 0.038 Uiso 1 1 calc R U . . .
H13B H 0.9975 0.3105 0.7918 0.038 Uiso 1 1 calc R U . . .
C14 C 0.9498(7) 0.4517(6) 0.6687(6) 0.0404(17) Uani 1 1 d . U . . .
H14A H 0.8694 0.4967 0.6498 0.061 Uiso 1 1 calc R U . . .
H14B H 1.0214 0.4128 0.5936 0.061 Uiso 1 1 calc R U . . .
H14C H 0.9799 0.5087 0.6964 0.061 Uiso 1 1 calc R U . . .
C15 C 0.7495(8) 0.3062(7) 0.9738(6) 0.0477(19) Uani 1 1 d . U . . .
H15A H 0.8267 0.2355 0.9766 0.057 Uiso 1 1 calc R U . . .
H15B H 0.6995 0.3368 1.0591 0.057 Uiso 1 1 calc R U . . .
C16 C 0.6622(8) 0.2644(7) 0.9383(7) 0.052(2) Uani 1 1 d . U . . .
H16A H 0.5821 0.3323 0.9411 0.078 Uiso 1 1 calc R U . . .
H16B H 0.6352 0.1973 0.9961 0.078 Uiso 1 1 calc R U . . .
H16C H 0.7102 0.2352 0.8534 0.078 Uiso 1 1 calc R U . . .
C17 C 0.8451(7) 0.4753(6) 0.9534(6) 0.0344(15) Uani 1 1 d . U . . .
H17A H 0.8970 0.5284 0.8924 0.041 Uiso 1 1 calc R U . . .
H17B H 0.9047 0.4163 0.9933 0.041 Uiso 1 1 calc R U . . .
C18 C 0.7249(9) 0.5540(8) 1.0526(8) 0.070(3) Uani 1 1 d . U . . .
H18A H 0.6673 0.6144 1.0131 0.104 Uiso 1 1 calc R U . . .
H18B H 0.7567 0.5966 1.0952 0.104 Uiso 1 1 calc R U . . .
H18C H 0.6734 0.5017 1.1135 0.104 Uiso 1 1 calc R U . . .
N2 N 0.7130(7) -0.0383(5) 0.7023(5) 0.0531(16) Uani 1 1 d D U . . .
H2 H 0.7406 0.0381 0.6661 0.064 Uiso 1 1 calc R U . . .
C19 C 0.5626(9) -0.0078(8) 0.7263(8) 0.070(2) Uani 1 1 d D U . . .
H19A H 0.5505 0.0101 0.6452 0.084 Uiso 1 1 calc R U . . .
H19B H 0.5311 -0.0806 0.7667 0.084 Uiso 1 1 calc R U . . .
C20 C 0.4778(10) 0.0982(9) 0.8061(9) 0.080(3) Uani 1 1 d D U . . .
H20A H 0.4770 0.0761 0.8910 0.121 Uiso 1 1 calc R U . . .
H20B H 0.3857 0.1201 0.8079 0.121 Uiso 1 1 calc R U . . .
H20C H 0.5145 0.1682 0.7720 0.121 Uiso 1 1 calc R U . . .
C21 C 0.7779(10) -0.1251(7) 0.6035(8) 0.074(2) Uani 1 1 d D U . . .
H21A H 0.7523 -0.2022 0.6342 0.088 Uiso 0.780(14) 1 calc R U P B 1
H21B H 0.7501 -0.0902 0.5317 0.088 Uiso 0.780(14) 1 calc R U P B 1
H21C H 0.8115 -0.0768 0.5251 0.088 Uiso 0.220(14) 1 calc R U P B 2
H21D H 0.7048 -0.1505 0.5981 0.088 Uiso 0.220(14) 1 calc R U P B 2
C22 C 0.9205(10) -0.1484(10) 0.5665(9) 0.059(3) Uani 0.780(14) 1 d D U P B 1
H22A H 0.9676 -0.2067 0.4998 0.088 Uiso 0.780(14) 1 calc R U P B 1
H22B H 0.9446 -0.0715 0.5362 0.088 Uiso 0.780(14) 1 calc R U P B 1
H22C H 0.9468 -0.1830 0.6382 0.088 Uiso 0.780(14) 1 calc R U P B 1
C22X C 0.891(3) -0.241(2) 0.597(3) 0.047(7) Uani 0.220(14) 1 d D U P B 2
H22D H 0.9157 -0.2828 0.5211 0.071 Uiso 0.220(14) 1 calc R U P B 2
H22E H 0.9688 -0.2212 0.5965 0.071 Uiso 0.220(14) 1 calc R U P B 2
H22F H 0.8609 -0.2958 0.6703 0.071 Uiso 0.220(14) 1 calc R U P B 2
C23 C 0.7469(10) -0.0765(7) 0.8165(7) 0.062(2) Uani 1 1 d D U . . .
H23A H 0.7006 -0.0083 0.8741 0.074 Uiso 0.648(14) 1 calc R U P C 1
H23B H 0.8449 -0.0923 0.7927 0.074 Uiso 0.648(14) 1 calc R U P C 1
H23C H 0.7440 -0.1624 0.8395 0.074 Uiso 0.352(14) 1 calc R U P C 2
H23D H 0.6741 -0.0259 0.8848 0.074 Uiso 0.352(14) 1 calc R U P C 2
C24 C 0.7067(15) -0.1911(10) 0.8845(11) 0.061(4) Uani 0.648(14) 1 d D U P C 1
H24A H 0.7312 -0.2118 0.9584 0.091 Uiso 0.648(14) 1 calc R U P C 1
H24B H 0.6094 -0.1755 0.9102 0.091 Uiso 0.648(14) 1 calc R U P C 1
H24C H 0.7538 -0.2595 0.8287 0.091 Uiso 0.648(14) 1 calc R U P C 1
C24X C 0.880(2) -0.069(2) 0.814(2) 0.069(5) Uani 0.352(14) 1 d D U P C 2
H24D H 0.8872 -0.0974 0.8955 0.104 Uiso 0.352(14) 1 calc R U P C 2
H24E H 0.9547 -0.1217 0.7497 0.104 Uiso 0.352(14) 1 calc R U P C 2
H24F H 0.8843 0.0156 0.7952 0.104 Uiso 0.352(14) 1 calc R U P C 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu O2 1.940(4) . ?
Cu O4 1.927(4) . ?
Cu O6 1.926(4) 2_666 ?
Cu O8 1.945(4) 2_666 ?
Cu O9 2.278(4) . ?
C1 C2 1.402(7) . ?
C1 C6 1.386(7) . ?
C1 C7 1.533(7) . ?
C2 C3 1.399(7) . ?
C2 C8 1.539(7) . ?
C3 H3 0.950 . ?
C3 C4 1.391(7) . ?
C4 C5 1.398(7) . ?
C4 C9 1.524(7) . ?
C5 C6 1.386(7) . ?
C5 C10 1.517(7) . ?
C6 H6 0.950 . ?
C7 O1 1.233(6) . ?
C7 O2 1.267(6) . ?
C8 O3 1.238(6) . ?
C8 O4 1.262(6) . ?
C9 O5 1.231(6) . ?
C9 O6 1.279(6) . ?
C10 O7 1.244(6) . ?
C10 O8 1.271(6) . ?
O6 Cu 1.926(4) 2_666 ?
O8 Cu 1.945(4) 2_666 ?
O9 H9 0.836(10) . ?
O9 C11 1.395(8) . ?
C11 H11A 0.990 . ?
C11 H11B 0.990 . ?
C11 H11C 0.990 . ?
C11 H11D 0.990 . ?
C11 C12 1.450(14) . ?
C11 C12X 1.448(16) . ?
C12 H12A 0.980 . ?
C12 H12B 0.980 . ?
C12 H12C 0.980 . ?
C12X H12D 0.980 . ?
C12X H12E 0.980 . ?
C12X H12F 0.980 . ?
N1 H1 1.000 . ?
N1 C13 1.497(7) . ?
N1 C15 1.520(8) . ?
N1 C17 1.485(7) . ?
C13 H13A 0.990 . ?
C13 H13B 0.990 . ?
C13 C14 1.518(8) . ?
C14 H14A 0.980 . ?
C14 H14B 0.980 . ?
C14 H14C 0.980 . ?
C15 H15A 0.990 . ?
C15 H15B 0.990 . ?
C15 C16 1.445(10) . ?
C16 H16A 0.980 . ?
C16 H16B 0.980 . ?
C16 H16C 0.980 . ?
C17 H17A 0.990 . ?
C17 H17B 0.990 . ?
C17 C18 1.523(9) . ?
C18 H18A 0.980 . ?
C18 H18B 0.980 . ?
C18 H18C 0.980 . ?
N2 H2 1.000 . ?
N2 C19 1.537(9) . ?
N2 C21 1.457(8) . ?
N2 C23 1.491(8) . ?
C19 H19A 0.990 . ?
C19 H19B 0.990 . ?
C19 C20 1.484(11) . ?
C20 H20A 0.980 . ?
C20 H20B 0.980 . ?
C20 H20C 0.980 . ?
C21 H21A 0.990 . ?
C21 H21B 0.990 . ?
C21 H21C 0.990 . ?
C21 H21D 0.990 . ?
C21 C22 1.436(11) . ?
C21 C22X 1.512(15) . ?
C22 H22A 0.980 . ?
C22 H22B 0.980 . ?
C22 H22C 0.980 . ?
C22X H22D 0.980 . ?
C22X H22E 0.980 . ?
C22X H22F 0.980 . ?
C23 H23A 0.990 . ?
C23 H23B 0.990 . ?
C23 H23C 0.990 . ?
C23 H23D 0.990 . ?
C23 C24 1.527(10) . ?
C23 C24X 1.525(14) . ?
C24 H24A 0.980 . ?
C24 H24B 0.980 . ?
C24 H24C 0.980 . ?
C24X H24D 0.980 . ?
C24X H24E 0.980 . ?
C24X H24F 0.980 . ?

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 Cu O4 89.42(16) . . ?
O2 Cu O6 89.67(16) . 2_666 ?
O2 Cu O8 177.11(15) . 2_666 ?
O2 Cu O9 91.64(15) . . ?
O4 Cu O6 171.63(15) . 2_666 ?
O4 Cu O8 90.12(17) . 2_666 ?
O4 Cu O9 93.89(15) . . ?
O6 Cu O8 90.37(16) 2_666 2_666 ?
O6 Cu O9 94.46(15) 2_666 . ?
O8 Cu O9 91.23(15) 2_666 . ?
C2 C1 C6 118.3(5) . . ?
C2 C1 C7 125.2(5) . . ?
C6 C1 C7 116.2(5) . . ?
C1 C2 C3 118.6(5) . . ?
C1 C2 C8 126.1(4) . . ?
C3 C2 C8 115.1(5) . . ?
C2 C3 H3 118.6 . . ?
C2 C3 C4 122.7(5) . . ?
H3 C3 C4 118.6 . . ?
C3 C4 C5 118.0(5) . . ?
C3 C4 C9 116.1(5) . . ?
C5 C4 C9 125.8(5) . . ?
C4 C5 C6 119.3(5) . . ?
C4 C5 C10 124.3(4) . . ?
C6 C5 C10 116.2(5) . . ?
C1 C6 C5 122.9(5) . . ?
C1 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
C1 C7 O1 117.2(4) . . ?
C1 C7 O2 119.2(5) . . ?
O1 C7 O2 123.6(5) . . ?
C2 C8 O3 116.7(5) . . ?
C2 C8 O4 118.8(5) . . ?
O3 C8 O4 124.5(5) . . ?
C4 C9 O5 116.9(5) . . ?
C4 C9 O6 119.3(5) . . ?
O5 C9 O6 123.8(5) . . ?
C5 C10 O7 117.5(4) . . ?
C5 C10 O8 120.1(5) . . ?
O7 C10 O8 122.3(5) . . ?
Cu O2 C7 124.1(3) . . ?
Cu O4 C8 125.6(3) . . ?
Cu O6 C9 126.8(4) 2_666 . ?
Cu O8 C10 127.2(3) 2_666 . ?
Cu O9 H9 124(5) . . ?
Cu O9 C11 122.4(4) . . ?
H9 O9 C11 105(5) . . ?
O9 C11 H11A 109.6 . . ?
O9 C11 H11B 109.6 . . ?
O9 C11 H11C 108.9 . . ?
O9 C11 H11D 108.9 . . ?
O9 C11 C12 110.5(8) . . ?
O9 C11 C12X 113.3(10) . . ?
H11A C11 H11B 108.1 . . ?
H11A C11 C12 109.6 . . ?
H11B C11 C12 109.6 . . ?
H11C C11 H11D 107.7 . . ?
H11C C11 C12X 108.9 . . ?
H11D C11 C12X 108.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C12X H12D 109.5 . . ?
C11 C12X H12E 109.5 . . ?
C11 C12X H12F 109.5 . . ?
H12D C12X H12E 109.5 . . ?
H12D C12X H12F 109.5 . . ?
H12E C12X H12F 109.5 . . ?
H1 N1 C13 108.4 . . ?
H1 N1 C15 108.4 . . ?
H1 N1 C17 108.4 . . ?
C13 N1 C15 110.5(5) . . ?
C13 N1 C17 111.4(5) . . ?
C15 N1 C17 109.7(5) . . ?
N1 C13 H13A 109.2 . . ?
N1 C13 H13B 109.2 . . ?
N1 C13 C14 112.2(5) . . ?
H13A C13 H13B 107.9 . . ?
H13A C13 C14 109.2 . . ?
H13B C13 C14 109.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 108.7 . . ?
N1 C15 H15B 108.7 . . ?
N1 C15 C16 114.2(6) . . ?
H15A C15 H15B 107.6 . . ?
H15A C15 C16 108.7 . . ?
H15B C15 C16 108.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 109.2 . . ?
N1 C17 H17B 109.2 . . ?
N1 C17 C18 111.9(6) . . ?
H17A C17 H17B 107.9 . . ?
H17A C17 C18 109.2 . . ?
H17B C17 C18 109.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
H2 N2 C19 107.0 . . ?
H2 N2 C21 107.0 . . ?
H2 N2 C23 107.0 . . ?
C19 N2 C21 103.9(6) . . ?
C19 N2 C23 114.5(6) . . ?
C21 N2 C23 116.9(6) . . ?
N2 C19 H19A 108.8 . . ?
N2 C19 H19B 108.8 . . ?
N2 C19 C20 113.6(6) . . ?
H19A C19 H19B 107.7 . . ?
H19A C19 C20 108.8 . . ?
H19B C19 C20 108.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 H21A 110.3 . . ?
N2 C21 H21B 110.3 . . ?
N2 C21 H21C 105.8 . . ?
N2 C21 H21D 105.8 . . ?
N2 C21 C22 107.2(8) . . ?
N2 C21 C22X 126.1(13) . . ?
H21A C21 H21B 108.5 . . ?
H21A C21 C22 110.3 . . ?
H21B C21 C22 110.3 . . ?
H21C C21 H21D 106.2 . . ?
H21C C21 C22X 105.8 . . ?
H21D C21 C22X 105.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C22X H22D 109.5 . . ?
C21 C22X H22E 109.5 . . ?
C21 C22X H22F 109.5 . . ?
H22D C22X H22E 109.5 . . ?
H22D C22X H22F 109.5 . . ?
H22E C22X H22F 109.5 . . ?
N2 C23 H23A 109.0 . . ?
N2 C23 H23B 109.0 . . ?
N2 C23 H23C 107.5 . . ?
N2 C23 H23D 107.5 . . ?
N2 C23 C24 113.0(7) . . ?
N2 C23 C24X 119.5(10) . . ?
H23A C23 H23B 107.8 . . ?
H23A C23 C24 109.0 . . ?
H23B C23 C24 109.0 . . ?
H23C C23 H23D 107.0 . . ?
H23C C23 C24X 107.5 . . ?
H23D C23 C24X 107.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C24X H24D 109.5 . . ?
C23 C24X H24E 109.5 . . ?
C23 C24X H24F 109.5 . . ?
H24D C24X H24E 109.5 . . ?
H24D C24X H24F 109.5 . . ?
H24E C24X H24F 109.5 . . ?

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
C6 C1 C2 C3 -1.0(8) . . . . ?
C6 C1 C2 C8 -176.1(5) . . . . ?
C7 C1 C2 C3 173.2(5) . . . . ?
C7 C1 C2 C8 -1.9(9) . . . . ?
C1 C2 C3 C4 4.0(8) . . . . ?
C8 C2 C3 C4 179.6(5) . . . . ?
C2 C3 C4 C5 -3.0(8) . . . . ?
C2 C3 C4 C9 -178.6(5) . . . . ?
C3 C4 C5 C6 -0.9(8) . . . . ?
C3 C4 C5 C10 -175.8(5) . . . . ?
C9 C4 C5 C6 174.1(5) . . . . ?
C9 C4 C5 C10 -0.7(9) . . . . ?
C4 C5 C6 C1 4.0(8) . . . . ?
C10 C5 C6 C1 179.2(5) . . . . ?
C2 C1 C6 C5 -3.0(8) . . . . ?
C7 C1 C6 C5 -177.7(5) . . . . ?
C2 C1 C7 O1 -135.8(6) . . . . ?
C2 C1 C7 O2 46.2(8) . . . . ?
C6 C1 C7 O1 38.4(7) . . . . ?
C6 C1 C7 O2 -139.6(5) . . . . ?
C1 C2 C8 O3 130.4(6) . . . . ?
C1 C2 C8 O4 -50.8(8) . . . . ?
C3 C2 C8 O3 -44.9(7) . . . . ?
C3 C2 C8 O4 133.9(5) . . . . ?
C3 C4 C9 O5 51.8(7) . . . . ?
C3 C4 C9 O6 -125.7(5) . . . . ?
C5 C4 C9 O5 -123.3(6) . . . . ?
C5 C4 C9 O6 59.2(8) . . . . ?
C4 C5 C10 O7 139.7(6) . . . . ?
C4 C5 C10 O8 -42.3(8) . . . . ?
C6 C5 C10 O7 -35.3(7) . . . . ?
C6 C5 C10 O8 142.7(5) . . . . ?
C1 C7 O2 Cu 10.0(7) . . . . ?
O1 C7 O2 Cu -167.8(4) . . . . ?
C2 C8 O4 Cu 2.3(7) . . . . ?
O3 C8 O4 Cu -178.9(4) . . . . ?
C4 C9 O6 Cu -16.3(7) . . . 2_666 ?
O5 C9 O6 Cu 166.4(4) . . . 2_666 ?
C5 C10 O8 Cu -13.2(7) . . . 2_666 ?
O7 C10 O8 Cu 164.7(4) . . . 2_666 ?
Cu O9 C11 C12 -71.3(9) . . . . ?
Cu O9 C11 C12X 138.2(11) . . . . ?
C15 N1 C13 C14 165.5(5) . . . . ?
C17 N1 C13 C14 -72.3(7) . . . . ?
C13 N1 C15 C16 -78.5(8) . . . . ?
C17 N1 C15 C16 158.4(6) . . . . ?
C13 N1 C17 C18 166.5(6) . . . . ?
C15 N1 C17 C18 -70.8(7) . . . . ?
C21 N2 C19 C20 -168.4(7) . . . . ?
C23 N2 C19 C20 63.0(8) . . . . ?
C19 N2 C21 C22 174.1(7) . . . . ?
C19 N2 C21 C22X -136.7(19) . . . . ?
C23 N2 C21 C22 -58.8(10) . . . . ?
C23 N2 C21 C22X -10(2) . . . . ?
C19 N2 C23 C24 60.0(10) . . . . ?
C19 N2 C23 C24X -160.4(11) . . . . ?
C21 N2 C23 C24 -61.7(11) . . . . ?
C21 N2 C23 C24X 77.9(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O9 H9 O3 0.836(10) 1.93(2) 2.734(5) 162(6) 2_676
N1 H1 O1 1.00 1.79 2.784(6) 173 .
N2 H2 O7 1.00 1.79 2.773(7) 166 .
N2 H2 O8 1.00 2.36 3.085(6) 129 .

_refine_diff_density_max         1.303
_refine_diff_density_min         -1.320
_refine_diff_density_rms         0.136

_exptl_crystal_recrystallization_method 
'Obtained direct from slow diffusion synthesis'
####################################################################### 
# 
# 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_wc5
_database_code_depnum_ccdc_archive 'CCDC 1044122'
_audit_update_record             
;
2015-01-16 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '4 C6 H16 N +,C22 H12 Cu2 O18 4-,2 C H4 O'
_chemical_formula_sum            'C48 H84 Cu2 N4 O20'
_chemical_formula_weight         1164.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.5053(11)
_cell_length_b                   11.5543(11)
_cell_length_c                   12.0160(11)
_cell_angle_alpha                78.671(2)
_cell_angle_beta                 64.251(2)
_cell_angle_gamma                71.747(2)
_cell_volume                     1362.9(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    8941
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      29.11

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_F_000             618
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.858
_shelx_estimated_absorpt_T_min   0.684
_shelx_estimated_absorpt_T_max   0.821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.680
_exptl_absorpt_correction_T_max  0.820
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART CCD diffractometer'
_diffrn_measurement_method       'narrow-frame ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11335
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_av_R_equivalents  0.0142
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.886
_diffrn_reflns_theta_max         29.126
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             6487
_reflns_number_gt                5709
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'local programs'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  SHELXL-2014/7
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL and local programs'
_refine_special_details          'Disorder resolved in one cation'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0694P)²+2.2682P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_extinction_coef       0.0043(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6487
_refine_ls_number_parameters     364
_refine_ls_number_restraints     214
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1368
_refine_ls_wR_factor_gt          0.1342
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Cu Cu 0.36682(3) 0.78665(3) 0.62699(3) 0.01855(11) Uani 1 1 d . . . . .
C1 C 0.6162(2) 0.5673(2) 0.6064(2) 0.0187(5) Uani 1 1 d . . . . .
C2 C 0.6558(2) 0.6229(2) 0.4853(2) 0.0180(5) Uani 1 1 d . . . . .
C3 C 0.7240(3) 0.5488(2) 0.3857(2) 0.0198(5) Uani 1 1 d . . . . .
H3 H 0.7562 0.5861 0.3041 0.024 Uiso 1 1 calc R U . . .
C4 C 0.7467(2) 0.4216(2) 0.4016(2) 0.0197(5) Uani 1 1 d . . . . .
C5 C 0.7052(2) 0.3666(2) 0.5224(2) 0.0196(5) Uani 1 1 d . . . . .
C6 C 0.6439(3) 0.4404(2) 0.6219(2) 0.0202(5) Uani 1 1 d . . . . .
H6 H 0.6200 0.4026 0.7036 0.024 Uiso 1 1 calc R U . . .
C7 C 0.5556(3) 0.6346(2) 0.7231(2) 0.0207(5) Uani 1 1 d . . . . .
C8 C 0.6391(3) 0.7598(2) 0.4538(2) 0.0202(5) Uani 1 1 d . . . . .
C9 C 0.8271(3) 0.3541(2) 0.2835(2) 0.0243(5) Uani 1 1 d . . . . .
C10 C 0.7290(3) 0.2302(2) 0.5546(3) 0.0225(5) Uani 1 1 d . . . . .
O1 O 0.6028(2) 0.59158(18) 0.80265(19) 0.0299(4) Uani 1 1 d . . . . .
O2 O 0.45870(19) 0.72901(17) 0.73796(17) 0.0244(4) Uani 1 1 d . . . . .
O3 O 0.7392(2) 0.79261(17) 0.37657(19) 0.0288(4) Uani 1 1 d . . . . .
O4 O 0.52467(19) 0.83307(16) 0.50341(18) 0.0255(4) Uani 1 1 d . . . . .
O5 O 0.9357(2) 0.3759(2) 0.2151(2) 0.0450(6) Uani 1 1 d . . . . .
O6 O 0.7776(2) 0.28336(17) 0.25813(17) 0.0257(4) Uani 1 1 d . . . . .
O7 O 0.7548(2) 0.18893(17) 0.6477(2) 0.0335(5) Uani 1 1 d . . . . .
O8 O 0.7195(2) 0.16253(16) 0.48927(19) 0.0258(4) Uani 1 1 d . . . . .
O9 O 0.2576(2) 0.97159(17) 0.70646(19) 0.0297(4) Uani 1 1 d D . . . .
H9 H 0.283(4) 1.035(2) 0.672(3) 0.045 Uiso 1 1 d D U . . .
C11 C 0.1150(4) 1.0000(3) 0.7580(5) 0.0648(14) Uani 1 1 d . . . . .
H11A H 0.0782 1.0815 0.7895 0.097 Uiso 1 1 calc R U . . .
H11B H 0.0846 0.9985 0.6939 0.097 Uiso 1 1 calc R U . . .
H11C H 0.0845 0.9395 0.8261 0.097 Uiso 1 1 calc R U . . .
N1 N 0.7776(3) 0.4005(2) 0.8710(2) 0.0314(5) Uani 1 1 d . . . . .
H1 H 0.7207 0.4689 0.8371 0.038 Uiso 1 1 calc R U . . .
C12 C 0.8997(3) 0.3473(3) 0.7600(3) 0.0382(7) Uani 1 1 d . . . . .
H12A H 0.9718 0.2989 0.7872 0.046 Uiso 1 1 calc R U . . .
H12B H 0.8780 0.2916 0.7233 0.046 Uiso 1 1 calc R U . . .
C13 C 0.9485(4) 0.4454(4) 0.6633(3) 0.0439(8) Uani 1 1 d . . . . .
H13A H 1.0275 0.4078 0.5929 0.066 Uiso 1 1 calc R U . . .
H13B H 0.8779 0.4926 0.6351 0.066 Uiso 1 1 calc R U . . .
H13C H 0.9717 0.4999 0.6989 0.066 Uiso 1 1 calc R U . . .
C14 C 0.8108(4) 0.4567(4) 0.9515(4) 0.0454(8) Uani 1 1 d . . . . .
H14A H 0.8637 0.5153 0.8998 0.054 Uiso 1 1 calc R U . . .
H14B H 0.8672 0.3918 0.9874 0.054 Uiso 1 1 calc R U . . .
C15 C 0.6895(4) 0.5223(4) 1.0555(3) 0.0496(9) Uani 1 1 d . . . . .
H15A H 0.7180 0.5570 1.1047 0.074 Uiso 1 1 calc R U . . .
H15B H 0.6341 0.5881 1.0208 0.074 Uiso 1 1 calc R U . . .
H15C H 0.6376 0.4645 1.1085 0.074 Uiso 1 1 calc R U . . .
C16 C 0.6950(4) 0.3070(3) 0.9380(3) 0.0417(8) Uani 1 1 d . . . . .
H16A H 0.6114 0.3468 1.0050 0.050 Uiso 1 1 calc R U . . .
H16B H 0.6703 0.2822 0.8787 0.050 Uiso 1 1 calc R U . . .
C17 C 0.7658(4) 0.1951(3) 0.9927(4) 0.0531(10) Uani 1 1 d . . . . .
H17A H 0.7074 0.1398 1.0338 0.080 Uiso 1 1 calc R U . . .
H17B H 0.8476 0.1538 0.9268 0.080 Uiso 1 1 calc R U . . .
H17C H 0.7886 0.2185 1.0533 0.080 Uiso 1 1 calc R U . . .
N2 N 0.7031(4) -0.0393(3) 0.6991(3) 0.0497(8) Uani 1 1 d D U . . .
H2 H 0.7343 0.0368 0.6647 0.060 Uiso 0.843(7) 1 calc R U P A 1
H2X H 0.6938 0.0499 0.6747 0.060 Uiso 0.157(7) 1 calc R U P A 2
C18 C 0.7324(6) -0.0840(4) 0.8118(4) 0.0451(11) Uani 0.843(7) 1 d D U P A 1
H18A H 0.6976 -0.0159 0.8660 0.054 Uiso 0.843(7) 1 calc R U P A 1
H18B H 0.8303 -0.1126 0.7871 0.054 Uiso 0.843(7) 1 calc R U P A 1
C19 C 0.6670(16) -0.1907(10) 0.8848(11) 0.155(5) Uani 0.843(7) 1 d D U P A 1
H19A H 0.6876 -0.2185 0.9582 0.232 Uiso 0.843(7) 1 calc R U P A 1
H19B H 0.5700 -0.1619 0.9104 0.232 Uiso 0.843(7) 1 calc R U P A 1
H19C H 0.7025 -0.2585 0.8315 0.232 Uiso 0.843(7) 1 calc R U P A 1
C20 C 0.5505(6) -0.0047(4) 0.7213(5) 0.0473(12) Uani 0.843(7) 1 d D U P A 1
H20A H 0.5436 0.0194 0.6403 0.057 Uiso 0.843(7) 1 calc R U P A 1
H20B H 0.5163 -0.0783 0.7568 0.057 Uiso 0.843(7) 1 calc R U P A 1
C21 C 0.4641(6) 0.0954(6) 0.8046(6) 0.0705(16) Uani 0.843(7) 1 d D U P A 1
H21A H 0.3718 0.1112 0.8134 0.106 Uiso 0.843(7) 1 calc R U P A 1
H21B H 0.4681 0.0717 0.8860 0.106 Uiso 0.843(7) 1 calc R U P A 1
H21C H 0.4954 0.1695 0.7693 0.106 Uiso 0.843(7) 1 calc R U P A 1
C22 C 0.7764(5) -0.1257(4) 0.6010(5) 0.0522(12) Uani 0.843(7) 1 d D U P A 1
H22A H 0.7568 -0.0898 0.5272 0.063 Uiso 0.843(7) 1 calc R U P A 1
H22B H 0.7468 -0.2021 0.6304 0.063 Uiso 0.843(7) 1 calc R U P A 1
C23 C 0.9240(6) -0.1538(6) 0.5669(7) 0.0749(17) Uani 0.843(7) 1 d D U P A 1
H23A H 0.9719 -0.2113 0.5015 0.112 Uiso 0.843(7) 1 calc R U P A 1
H23B H 0.9532 -0.0782 0.5369 0.112 Uiso 0.843(7) 1 calc R U P A 1
H23C H 0.9432 -0.1903 0.6398 0.112 Uiso 0.843(7) 1 calc R U P A 1
C18X C 0.670(2) -0.0555(16) 0.8438(13) 0.035(5) Uiso 0.157(7) 1 d D U P A 2
H18C H 0.7275 -0.0220 0.8631 0.042 Uiso 0.157(7) 1 calc R U P A 2
H18D H 0.5748 -0.0158 0.8926 0.042 Uiso 0.157(7) 1 calc R U P A 2
C19X C 0.6996(17) -0.1959(14) 0.8681(17) 0.015(4) Uiso 0.157(7) 1 d D U P A 2
H19D H 0.6824 -0.2177 0.9559 0.022 Uiso 0.157(7) 1 calc R U P A 2
H19E H 0.6421 -0.2264 0.8465 0.022 Uiso 0.157(7) 1 calc R U P A 2
H19F H 0.7935 -0.2326 0.8173 0.022 Uiso 0.157(7) 1 calc R U P A 2
C20X C 0.597(2) -0.070(3) 0.683(3) 0.075(8) Uiso 0.157(7) 1 d D U P A 2
H20C H 0.5925 -0.1554 0.7118 0.090 Uiso 0.157(7) 1 calc R U P A 2
H20D H 0.6050 -0.0538 0.5958 0.090 Uiso 0.157(7) 1 calc R U P A 2
C21X C 0.479(2) 0.023(2) 0.769(2) 0.044(6) Uiso 0.157(7) 1 d D U P A 2
H21D H 0.3953 0.0168 0.7706 0.066 Uiso 0.157(7) 1 calc R U P A 2
H21E H 0.4775 0.0054 0.8526 0.066 Uiso 0.157(7) 1 calc R U P A 2
H21F H 0.4898 0.1057 0.7381 0.066 Uiso 0.157(7) 1 calc R U P A 2
C22X C 0.8447(18) -0.106(2) 0.614(3) 0.071(8) Uiso 0.157(7) 1 d D U P A 2
H22C H 0.8610 -0.0614 0.5312 0.085 Uiso 0.157(7) 1 calc R U P A 2
H22D H 0.9056 -0.0885 0.6431 0.085 Uiso 0.157(7) 1 calc R U P A 2
C23X C 0.897(2) -0.2403(16) 0.590(2) 0.037(5) Uiso 0.157(7) 1 d D U P A 2
H23D H 0.9911 -0.2569 0.5317 0.055 Uiso 0.157(7) 1 calc R U P A 2
H23E H 0.8898 -0.2892 0.6683 0.055 Uiso 0.157(7) 1 calc R U P A 2
H23F H 0.8447 -0.2617 0.5551 0.055 Uiso 0.157(7) 1 calc R U P A 2
O10 O 1.1098(6) 0.2988(7) -0.0223(8) 0.175(3) Uani 1 1 d . . . . .
H10 H 1.0577 0.3217 0.0489 0.262 Uiso 1 1 d R U . . .
C24 C 1.0988(10) 0.1906(8) -0.0216(9) 0.130(3) Uani 1 1 d . . . . .
H24A H 1.1432 0.1646 -0.1064 0.194 Uiso 1 1 calc R U . . .
H24B H 1.0041 0.1920 0.0117 0.194 Uiso 1 1 calc R U . . .
H24C H 1.1408 0.1332 0.0303 0.194 Uiso 1 1 calc R U . . .


_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
Cu O2 1.9426(19) . ?
Cu O4 1.9352(19) . ?
Cu O6 1.9320(19) 2_666 ?
Cu O8 1.9497(19) 2_666 ?
Cu O9 2.2658(19) . ?
C1 C2 1.406(3) . ?
C1 C6 1.392(3) . ?
C1 C7 1.515(3) . ?
C2 C3 1.395(3) . ?
C2 C8 1.523(3) . ?
C3 H3 0.950 . ?
C3 C4 1.399(3) . ?
C4 C5 1.402(4) . ?
C4 C9 1.524(3) . ?
C5 C6 1.395(3) . ?
C5 C10 1.513(3) . ?
C6 H6 0.950 . ?
C7 O1 1.246(3) . ?
C7 O2 1.267(3) . ?
C8 O3 1.240(3) . ?
C8 O4 1.274(3) . ?
C9 O5 1.234(4) . ?
C9 O6 1.275(3) . ?
C10 O7 1.248(3) . ?
C10 O8 1.268(3) . ?
O6 Cu 1.9319(19) 2_666 ?
O8 Cu 1.9497(19) 2_666 ?
O9 H9 0.835(10) . ?
O9 C11 1.429(4) . ?
C11 H11A 0.980 . ?
C11 H11B 0.980 . ?
C11 H11C 0.980 . ?
N1 H1 1.000 . ?
N1 C12 1.511(4) . ?
N1 C14 1.493(4) . ?
N1 C16 1.534(4) . ?
C12 H12A 0.990 . ?
C12 H12B 0.990 . ?
C12 C13 1.505(5) . ?
C13 H13A 0.980 . ?
C13 H13B 0.980 . ?
C13 H13C 0.980 . ?
C14 H14A 0.990 . ?
C14 H14B 0.990 . ?
C14 C15 1.510(5) . ?
C15 H15A 0.980 . ?
C15 H15B 0.980 . ?
C15 H15C 0.980 . ?
C16 H16A 0.990 . ?
C16 H16B 0.990 . ?
C16 C17 1.496(5) . ?
C17 H17A 0.980 . ?
C17 H17B 0.980 . ?
C17 H17C 0.980 . ?
N2 H2 1.000 . ?
N2 H2X 1.000 . ?
N2 C18 1.492(5) . ?
N2 C20 1.583(6) . ?
N2 C22 1.472(5) . ?
N2 C18X 1.593(13) . ?
N2 C20X 1.472(14) . ?
N2 C22X 1.539(13) . ?
C18 H18A 0.990 . ?
C18 H18B 0.990 . ?
C18 C19 1.561(8) . ?
C19 H19A 0.980 . ?
C19 H19B 0.980 . ?
C19 H19C 0.980 . ?
C20 H20A 0.990 . ?
C20 H20B 0.990 . ?
C20 C21 1.482(8) . ?
C21 H21A 0.980 . ?
C21 H21B 0.980 . ?
C21 H21C 0.980 . ?
C22 H22A 0.990 . ?
C22 H22B 0.990 . ?
C22 C23 1.503(7) . ?
C23 H23A 0.980 . ?
C23 H23B 0.980 . ?
C23 H23C 0.980 . ?
C18X H18C 0.990 . ?
C18X H18D 0.990 . ?
C18X C19X 1.545(14) . ?
C19X H19D 0.980 . ?
C19X H19E 0.980 . ?
C19X H19F 0.980 . ?
C20X H20C 0.990 . ?
C20X H20D 0.990 . ?
C20X C21X 1.538(16) . ?
C21X H21D 0.980 . ?
C21X H21E 0.980 . ?
C21X H21F 0.980 . ?
C22X H22C 0.990 . ?
C22X H22D 0.990 . ?
C22X C23X 1.519(15) . ?
C23X H23D 0.980 . ?
C23X H23E 0.980 . ?
C23X H23F 0.980 . ?
O10 H10 0.840 . ?
O10 C24 1.293(9) . ?
C24 H24A 0.980 . ?
C24 H24B 0.980 . ?
C24 H24C 0.980 . ?

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 Cu O4 88.69(9) . . ?
O2 Cu O6 90.31(9) . 2_666 ?
O2 Cu O8 177.12(8) . 2_666 ?
O2 Cu O9 94.74(8) . . ?
O4 Cu O6 171.61(8) . 2_666 ?
O4 Cu O8 90.42(9) . 2_666 ?
O4 Cu O9 96.67(8) . . ?
O6 Cu O8 90.18(9) 2_666 2_666 ?
O6 Cu O9 91.71(8) 2_666 . ?
O8 Cu O9 88.08(8) 2_666 . ?
C2 C1 C6 118.5(2) . . ?
C2 C1 C7 124.8(2) . . ?
C6 C1 C7 116.5(2) . . ?
C1 C2 C3 118.8(2) . . ?
C1 C2 C8 124.5(2) . . ?
C3 C2 C8 116.5(2) . . ?
C2 C3 H3 118.8 . . ?
C2 C3 C4 122.4(2) . . ?
H3 C3 C4 118.8 . . ?
C3 C4 C5 118.6(2) . . ?
C3 C4 C9 115.7(2) . . ?
C5 C4 C9 125.5(2) . . ?
C4 C5 C6 118.8(2) . . ?
C4 C5 C10 124.8(2) . . ?
C6 C5 C10 116.3(2) . . ?
C1 C6 C5 122.7(2) . . ?
C1 C6 H6 118.6 . . ?
C5 C6 H6 118.6 . . ?
C1 C7 O1 117.3(2) . . ?
C1 C7 O2 120.1(2) . . ?
O1 C7 O2 122.6(2) . . ?
C2 C8 O3 116.7(2) . . ?
C2 C8 O4 119.3(2) . . ?
O3 C8 O4 123.9(2) . . ?
C4 C9 O5 116.9(2) . . ?
C4 C9 O6 119.3(2) . . ?
O5 C9 O6 123.8(2) . . ?
C5 C10 O7 117.7(2) . . ?
C5 C10 O8 119.9(2) . . ?
O7 C10 O8 122.4(2) . . ?
Cu O2 C7 123.90(17) . . ?
Cu O4 C8 125.36(16) . . ?
Cu O6 C9 126.39(17) 2_666 . ?
Cu O8 C10 127.29(17) 2_666 . ?
Cu O9 H9 123(3) . . ?
Cu O9 C11 116.2(2) . . ?
H9 O9 C11 110(3) . . ?
O9 C11 H11A 109.5 . . ?
O9 C11 H11B 109.5 . . ?
O9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
H1 N1 C12 106.0 . . ?
H1 N1 C14 106.0 . . ?
H1 N1 C16 106.0 . . ?
C12 N1 C14 112.3(3) . . ?
C12 N1 C16 110.5(2) . . ?
C14 N1 C16 115.2(3) . . ?
N1 C12 H12A 109.3 . . ?
N1 C12 H12B 109.3 . . ?
N1 C12 C13 111.7(3) . . ?
H12A C12 H12B 107.9 . . ?
H12A C12 C13 109.3 . . ?
H12B C12 C13 109.3 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 H14A 108.9 . . ?
N1 C14 H14B 108.9 . . ?
N1 C14 C15 113.5(3) . . ?
H14A C14 H14B 107.7 . . ?
H14A C14 C15 108.9 . . ?
H14B C14 C15 108.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16A 108.8 . . ?
N1 C16 H16B 108.8 . . ?
N1 C16 C17 113.9(3) . . ?
H16A C16 H16B 107.7 . . ?
H16A C16 C17 108.8 . . ?
H16B C16 C17 108.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
H2 N2 C18 106.8 . . ?
H2 N2 C20 106.8 . . ?
H2 N2 C22 106.8 . . ?
H2X N2 C18X 106.3 . . ?
H2X N2 C20X 106.3 . . ?
H2X N2 C22X 106.3 . . ?
C18 N2 C20 115.7(4) . . ?
C18 N2 C22 113.1(3) . . ?
C20 N2 C22 107.2(3) . . ?
C18X N2 C20X 107.3(14) . . ?
C18X N2 C22X 116.4(15) . . ?
C20X N2 C22X 113.4(14) . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
N2 C18 C19 110.9(5) . . ?
H18A C18 H18B 108.1 . . ?
H18A C18 C19 109.5 . . ?
H18B C18 C19 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 H20A 108.6 . . ?
N2 C20 H20B 108.6 . . ?
N2 C20 C21 114.6(4) . . ?
H20A C20 H20B 107.6 . . ?
H20A C20 C21 108.6 . . ?
H20B C20 C21 108.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C22 H22A 109.6 . . ?
N2 C22 H22B 109.6 . . ?
N2 C22 C23 110.1(4) . . ?
H22A C22 H22B 108.2 . . ?
H22A C22 C23 109.6 . . ?
H22B C22 C23 109.6 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C18X H18C 111.4 . . ?
N2 C18X H18D 111.4 . . ?
N2 C18X C19X 101.8(12) . . ?
H18C C18X H18D 109.3 . . ?
H18C C18X C19X 111.4 . . ?
H18D C18X C19X 111.4 . . ?
C18X C19X H19D 109.5 . . ?
C18X C19X H19E 109.5 . . ?
C18X C19X H19F 109.5 . . ?
H19D C19X H19E 109.5 . . ?
H19D C19X H19F 109.5 . . ?
H19E C19X H19F 109.5 . . ?
N2 C20X H20C 112.4 . . ?
N2 C20X H20D 112.4 . . ?
N2 C20X C21X 96.6(14) . . ?
H20C C20X H20D 110.0 . . ?
H20C C20X C21X 112.4 . . ?
H20D C20X C21X 112.4 . . ?
C20X C21X H21D 109.5 . . ?
C20X C21X H21E 109.5 . . ?
C20X C21X H21F 109.5 . . ?
H21D C21X H21E 109.5 . . ?
H21D C21X H21F 109.5 . . ?
H21E C21X H21F 109.5 . . ?
N2 C22X H22C 105.5 . . ?
N2 C22X H22D 105.5 . . ?
N2 C22X C23X 127.2(17) . . ?
H22C C22X H22D 106.1 . . ?
H22C C22X C23X 105.5 . . ?
H22D C22X C23X 105.5 . . ?
C22X C23X H23D 109.5 . . ?
C22X C23X H23E 109.5 . . ?
C22X C23X H23F 109.5 . . ?
H23D C23X H23E 109.5 . . ?
H23D C23X H23F 109.5 . . ?
H23E C23X H23F 109.5 . . ?
H10 O10 C24 105.1 . . ?
O10 C24 H24A 109.5 . . ?
O10 C24 H24B 109.5 . . ?
O10 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
C6 C1 C2 C3 -1.6(4) . . . . ?
C6 C1 C2 C8 -176.6(2) . . . . ?
C7 C1 C2 C3 172.9(2) . . . . ?
C7 C1 C2 C8 -2.1(4) . . . . ?
C1 C2 C3 C4 4.3(4) . . . . ?
C8 C2 C3 C4 179.7(2) . . . . ?
C2 C3 C4 C5 -3.3(4) . . . . ?
C2 C3 C4 C9 -177.8(2) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C3 C4 C5 C10 -176.7(2) . . . . ?
C9 C4 C5 C6 173.5(2) . . . . ?
C9 C4 C5 C10 -2.7(4) . . . . ?
C2 C1 C6 C5 -2.1(4) . . . . ?
C7 C1 C6 C5 -177.0(2) . . . . ?
C4 C5 C6 C1 3.2(4) . . . . ?
C10 C5 C6 C1 179.7(2) . . . . ?
C2 C1 C7 O1 -132.1(3) . . . . ?
C2 C1 C7 O2 49.5(4) . . . . ?
C6 C1 C7 O1 42.4(3) . . . . ?
C6 C1 C7 O2 -136.0(3) . . . . ?
C1 C2 C8 O3 129.9(3) . . . . ?
C1 C2 C8 O4 -52.6(4) . . . . ?
C3 C2 C8 O3 -45.2(3) . . . . ?
C3 C2 C8 O4 132.2(3) . . . . ?
C3 C4 C9 O5 53.0(4) . . . . ?
C3 C4 C9 O6 -124.1(3) . . . . ?
C5 C4 C9 O5 -121.2(3) . . . . ?
C5 C4 C9 O6 61.8(4) . . . . ?
C4 C5 C10 O7 142.8(3) . . . . ?
C4 C5 C10 O8 -38.7(4) . . . . ?
C6 C5 C10 O7 -33.6(4) . . . . ?
C6 C5 C10 O8 145.0(3) . . . . ?
C1 C7 O2 Cu 6.8(3) . . . . ?
O1 C7 O2 Cu -171.5(2) . . . . ?
C2 C8 O4 Cu 4.2(3) . . . . ?
O3 C8 O4 Cu -178.5(2) . . . . ?
C4 C9 O6 Cu -19.1(4) . . . 2_666 ?
O5 C9 O6 Cu 164.1(2) . . . 2_666 ?
C5 C10 O8 Cu -17.2(4) . . . 2_666 ?
O7 C10 O8 Cu 161.3(2) . . . 2_666 ?
C14 N1 C12 C13 -75.0(4) . . . . ?
C16 N1 C12 C13 154.9(3) . . . . ?
C12 N1 C14 C15 173.8(3) . . . . ?
C16 N1 C14 C15 -58.5(4) . . . . ?
C12 N1 C16 C17 64.1(4) . . . . ?
C14 N1 C16 C17 -64.5(4) . . . . ?
C20 N2 C18 C19 52.2(8) . . . . ?
C22 N2 C18 C19 -72.0(9) . . . . ?
C18 N2 C20 C21 61.2(5) . . . . ?
C22 N2 C20 C21 -171.6(4) . . . . ?
C18 N2 C22 C23 -56.4(5) . . . . ?
C20 N2 C22 C23 174.9(4) . . . . ?
C20X N2 C18X C19X 71.6(19) . . . . ?
C22X N2 C18X C19X -56.7(19) . . . . ?
C18X N2 C20X C21X 56(2) . . . . ?
C22X N2 C20X C21X -173.7(19) . . . . ?
C18X N2 C22X C23X 78(3) . . . . ?
C20X N2 C22X C23X -47(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O9 H9 O3 0.835(10) 1.934(19) 2.717(3) 156(4) 2_676
O10 H10 O5 0.84 1.96 2.803(8) 180 .
N1 H1 O1 1.00 1.75 2.745(3) 171 .
N2 H2 O7 1.00 1.81 2.778(3) 163 .
N2 H2X O7 1.00 1.87 2.778(3) 150 .

_refine_diff_density_max         1.108
_refine_diff_density_min         -0.902
_refine_diff_density_rms         0.088

_exptl_crystal_recrystallization_method 
'Obtained direct from slow diffusion synthesis'
####################################################################### 
# 
# 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_wc19
_database_code_depnum_ccdc_archive 'CCDC 1044123'
_audit_update_record             
;
2015-01-16 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'2 N H4 +,Cu N4 H12 2+, 2 C10 H11 Cu N3 O8 2-,2H2 O'
_chemical_formula_sum            'C20 H46 Cu3 N12 O18'
_chemical_formula_weight         933.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.2343(7)
_cell_length_b                   19.5788(16)
_cell_length_c                   10.9336(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.371(2)
_cell_angle_gamma                90
_cell_volume                     1733.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    4625
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      28.59

_exptl_crystal_description       Block
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.788
_exptl_crystal_F_000             962
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.917
_shelx_estimated_absorpt_T_min   0.626
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.630
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker SMART 1K CCD diffractometer'
_diffrn_measurement_method       'narrow-frame ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11979
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.080
_diffrn_reflns_theta_max         28.667
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.885
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             3952
_reflns_number_gt                3125
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'local programs'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  SHELXL-2014/7
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0360P)²+3.5743P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3952
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0904
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.83314(5) 0.45250(2) 0.89782(4) 0.01185(11) Uani 1 1 d . . . . .
Cu2 Cu 0.5000 0.5000 0.5000 0.01365(14) Uani 1 2 d S . P . .
C1 C 0.8395(4) 0.66351(16) 1.0096(3) 0.0094(6) Uani 1 1 d . . . . .
C2 C 0.7750(4) 0.68894(16) 1.1110(3) 0.0100(6) Uani 1 1 d . . . . .
C3 C 0.8240(4) 0.75331(17) 1.1570(3) 0.0112(6) Uani 1 1 d . . . . .
H3 H 0.7758 0.7720 1.2223 0.013 Uiso 1 1 calc R U . . .
C4 C 0.9423(4) 0.79108(16) 1.1097(3) 0.0105(6) Uani 1 1 d . . . . .
C5 C 1.0156(4) 0.76329(16) 1.0157(3) 0.0103(6) Uani 1 1 d . . . . .
C6 C 0.9604(4) 0.70035(16) 0.9644(3) 0.0117(6) Uani 1 1 d . . . . .
H6 H 1.0062 0.6824 0.8974 0.014 Uiso 1 1 calc R U . . .
C7 C 0.7812(4) 0.59822(17) 0.9446(3) 0.0109(6) Uani 1 1 d . . . . .
C8 C 0.6659(4) 0.64542(17) 1.1778(3) 0.0116(6) Uani 1 1 d . . . . .
C9 C 0.9959(4) 0.86051(16) 1.1651(3) 0.0106(6) Uani 1 1 d . . . . .
C10 C 1.1592(4) 0.79754(17) 0.9718(3) 0.0133(7) Uani 1 1 d . . . . .
O1 O 0.6383(3) 0.59621(12) 0.8820(2) 0.0165(5) Uani 1 1 d . . . . .
O2 O 0.8864(3) 0.55000(11) 0.9523(2) 0.0110(5) Uani 1 1 d . . . . .
O3 O 0.5903(3) 0.67395(12) 1.2537(2) 0.0173(5) Uani 1 1 d . . . . .
O4 O 0.6609(3) 0.58208(12) 1.1559(2) 0.0196(6) Uani 1 1 d . . . . .
O5 O 0.8844(3) 0.90389(12) 1.1621(2) 0.0187(5) Uani 1 1 d . . . . .
O6 O 1.1460(3) 0.86896(12) 1.2108(2) 0.0175(5) Uani 1 1 d . . . . .
O7 O 1.1364(3) 0.85293(13) 0.9162(2) 0.0233(6) Uani 1 1 d . . . . .
O8 O 1.2942(3) 0.76500(14) 0.9959(3) 0.0231(6) Uani 1 1 d . . . . .
N1 N 0.7057(4) 0.44458(17) 1.0385(3) 0.0152(6) Uani 1 1 d . . . . .
H1A H 0.761(5) 0.422(2) 1.101(4) 0.023 Uiso 1 1 d . U . . .
H1B H 0.687(5) 0.485(2) 1.068(4) 0.023 Uiso 1 1 d . U . . .
H1C H 0.620(6) 0.427(2) 1.020(4) 0.023 Uiso 1 1 d . U . . .
N2 N 0.7626(4) 0.35864(16) 0.8355(3) 0.0163(6) Uani 1 1 d . . . . .
H2A H 0.669(6) 0.361(2) 0.796(4) 0.025 Uiso 1 1 d . U . . .
H2B H 0.753(5) 0.325(2) 0.897(4) 0.025 Uiso 1 1 d . U . . .
H2C H 0.814(5) 0.342(2) 0.783(4) 0.025 Uiso 1 1 d . U . . .
N3 N 0.9735(4) 0.46379(15) 0.7697(3) 0.0126(6) Uani 1 1 d . . . . .
H3A H 0.944(5) 0.434(2) 0.711(4) 0.019 Uiso 1 1 d . U . . .
H3B H 0.959(5) 0.506(2) 0.747(4) 0.019 Uiso 1 1 d . U . . .
H3C H 1.070(6) 0.454(2) 0.803(4) 0.019 Uiso 1 1 d . U . . .
N4 N 0.7369(4) 0.48656(18) 0.4760(3) 0.0193(7) Uani 1 1 d . . . . .
H4A H 0.769(6) 0.447(3) 0.499(4) 0.029 Uiso 1 1 d . U . . .
H4B H 0.803(6) 0.519(2) 0.513(4) 0.029 Uiso 1 1 d . U . . .
H4C H 0.749(6) 0.489(2) 0.405(5) 0.029 Uiso 1 1 d . U . . .
N5 N 0.5438(4) 0.60261(17) 0.5061(3) 0.0177(7) Uani 1 1 d . . . . .
H5A H 0.460(6) 0.621(2) 0.523(4) 0.027 Uiso 1 1 d . U . . .
H5B H 0.621(6) 0.611(2) 0.560(4) 0.027 Uiso 1 1 d . U . . .
H5C H 0.572(5) 0.617(2) 0.436(4) 0.027 Uiso 1 1 d . U . . .
N6 N 0.4291(4) 0.79176(17) 1.3051(3) 0.0181(7) Uani 1 1 d . . . . .
H6A H 0.503(6) 0.824(2) 1.331(4) 0.027 Uiso 1 1 d . U . . .
H6B H 0.397(5) 0.772(2) 1.375(4) 0.027 Uiso 1 1 d . U . . .
H6C H 0.471(6) 0.761(2) 1.277(4) 0.027 Uiso 1 1 d . U . . .
H6D H 0.346(6) 0.807(2) 1.261(4) 0.027 Uiso 1 1 d . U . . .
O9 O 0.5715(3) 0.48664(14) 0.7313(2) 0.0164(5) Uani 1 1 d . . . . .
H9A H 0.507(6) 0.464(2) 0.754(4) 0.025 Uiso 1 1 d . U . . .
H9B H 0.584(6) 0.524(2) 0.763(4) 0.025 Uiso 1 1 d . U . . .


_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 2.024(2) . ?
Cu1 N1 2.018(3) . ?
Cu1 N2 2.009(3) . ?
Cu1 N3 1.982(3) . ?
Cu2 N4 2.031(3) . ?
Cu2 N4 2.031(3) 3_666 ?
Cu2 N5 2.040(3) . ?
Cu2 N5 2.040(3) 3_666 ?
C1 C2 1.404(5) . ?
C1 C6 1.389(5) . ?
C1 C7 1.499(4) . ?
C2 C3 1.390(5) . ?
C2 C8 1.518(5) . ?
C3 H3 0.950 . ?
C3 C4 1.395(5) . ?
C4 C5 1.393(5) . ?
C4 C9 1.521(4) . ?
C5 C6 1.396(4) . ?
C5 C10 1.510(5) . ?
C6 H6 0.950 . ?
C7 O1 1.250(4) . ?
C7 O2 1.274(4) . ?
C8 O3 1.254(4) . ?
C8 O4 1.262(4) . ?
C9 O5 1.247(4) . ?
C9 O6 1.258(4) . ?
C10 O7 1.241(4) . ?
C10 O8 1.267(4) . ?
N1 H1A 0.87(5) . ?
N1 H1B 0.88(5) . ?
N1 H1C 0.78(5) . ?
N2 H2A 0.81(5) . ?
N2 H2B 0.95(5) . ?
N2 H2C 0.85(5) . ?
N3 H3A 0.87(4) . ?
N3 H3B 0.86(4) . ?
N3 H3C 0.84(4) . ?
N4 H4A 0.85(5) . ?
N4 H4B 0.89(5) . ?
N4 H4C 0.80(5) . ?
N5 H5A 0.83(5) . ?
N5 H5B 0.80(5) . ?
N5 H5C 0.88(5) . ?
N6 H6A 0.89(5) . ?
N6 H6B 0.93(5) . ?
N6 H6C 0.78(5) . ?
N6 H6D 0.82(5) . ?
O9 H9A 0.77(5) . ?
O9 H9B 0.80(5) . ?

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 N1 87.88(12) . . ?
O2 Cu1 N2 175.24(11) . . ?
O2 Cu1 N3 88.84(11) . . ?
N1 Cu1 N2 91.71(14) . . ?
N1 Cu1 N3 175.21(13) . . ?
N2 Cu1 N3 91.85(14) . . ?
N4 Cu2 N4 180.00(3) . 3_666 ?
N4 Cu2 N5 87.90(14) . . ?
N4 Cu2 N5 92.10(14) 3_666 . ?
N4 Cu2 N5 92.10(14) . 3_666 ?
N4 Cu2 N5 87.90(14) 3_666 3_666 ?
N5 Cu2 N5 180.00(18) . 3_666 ?
C2 C1 C6 119.6(3) . . ?
C2 C1 C7 122.8(3) . . ?
C6 C1 C7 117.6(3) . . ?
C1 C2 C3 118.8(3) . . ?
C1 C2 C8 121.5(3) . . ?
C3 C2 C8 119.5(3) . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.5(3) . . ?
H3 C3 C4 119.2 . . ?
C3 C4 C5 119.4(3) . . ?
C3 C4 C9 119.9(3) . . ?
C5 C4 C9 120.7(3) . . ?
C4 C5 C6 119.2(3) . . ?
C4 C5 C10 121.9(3) . . ?
C6 C5 C10 118.8(3) . . ?
C1 C6 C5 121.2(3) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C1 C7 O1 118.4(3) . . ?
C1 C7 O2 116.4(3) . . ?
O1 C7 O2 125.1(3) . . ?
C2 C8 O3 118.4(3) . . ?
C2 C8 O4 117.5(3) . . ?
O3 C8 O4 124.0(3) . . ?
C4 C9 O5 116.0(3) . . ?
C4 C9 O6 118.0(3) . . ?
O5 C9 O6 125.9(3) . . ?
C5 C10 O7 119.0(3) . . ?
C5 C10 O8 114.8(3) . . ?
O7 C10 O8 126.2(3) . . ?
Cu1 O2 C7 124.8(2) . . ?
Cu1 N1 H1A 112(3) . . ?
Cu1 N1 H1B 111(3) . . ?
Cu1 N1 H1C 114(3) . . ?
H1A N1 H1B 106(4) . . ?
H1A N1 H1C 107(4) . . ?
H1B N1 H1C 107(4) . . ?
Cu1 N2 H2A 109(3) . . ?
Cu1 N2 H2B 116(3) . . ?
Cu1 N2 H2C 116(3) . . ?
H2A N2 H2B 102(4) . . ?
H2A N2 H2C 102(4) . . ?
H2B N2 H2C 110(4) . . ?
Cu1 N3 H3A 109(3) . . ?
Cu1 N3 H3B 104(3) . . ?
Cu1 N3 H3C 107(3) . . ?
H3A N3 H3B 115(4) . . ?
H3A N3 H3C 106(4) . . ?
H3B N3 H3C 114(4) . . ?
Cu2 N4 H4A 109(3) . . ?
Cu2 N4 H4B 112(3) . . ?
Cu2 N4 H4C 114(3) . . ?
H4A N4 H4B 113(4) . . ?
H4A N4 H4C 105(5) . . ?
H4B N4 H4C 103(4) . . ?
Cu2 N5 H5A 107(3) . . ?
Cu2 N5 H5B 110(3) . . ?
Cu2 N5 H5C 111(3) . . ?
H5A N5 H5B 109(4) . . ?
H5A N5 H5C 114(4) . . ?
H5B N5 H5C 106(4) . . ?
H6A N6 H6B 108(4) . . ?
H6A N6 H6C 110(4) . . ?
H6A N6 H6D 113(4) . . ?
H6B N6 H6C 103(4) . . ?
H6B N6 H6D 107(4) . . ?
H6C N6 H6D 114(5) . . ?
H9A O9 H9B 116(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
C6 C1 C2 C3 5.3(4) . . . . ?
C6 C1 C2 C8 -169.2(3) . . . . ?
C7 C1 C2 C3 -173.3(3) . . . . ?
C7 C1 C2 C8 12.2(5) . . . . ?
C1 C2 C3 C4 -3.8(5) . . . . ?
C8 C2 C3 C4 170.8(3) . . . . ?
C2 C3 C4 C5 -1.2(5) . . . . ?
C2 C3 C4 C9 -178.3(3) . . . . ?
C3 C4 C5 C6 4.7(5) . . . . ?
C3 C4 C5 C10 -172.2(3) . . . . ?
C9 C4 C5 C6 -178.2(3) . . . . ?
C9 C4 C5 C10 4.9(5) . . . . ?
C2 C1 C6 C5 -1.9(5) . . . . ?
C7 C1 C6 C5 176.8(3) . . . . ?
C4 C5 C6 C1 -3.2(5) . . . . ?
C10 C5 C6 C1 173.8(3) . . . . ?
C2 C1 C7 O1 68.8(4) . . . . ?
C2 C1 C7 O2 -115.1(3) . . . . ?
C6 C1 C7 O1 -109.9(4) . . . . ?
C6 C1 C7 O2 66.3(4) . . . . ?
C1 C2 C8 O3 -168.5(3) . . . . ?
C1 C2 C8 O4 13.5(4) . . . . ?
C3 C2 C8 O3 17.1(4) . . . . ?
C3 C2 C8 O4 -160.9(3) . . . . ?
C3 C4 C9 O5 -58.5(4) . . . . ?
C3 C4 C9 O6 120.7(3) . . . . ?
C5 C4 C9 O5 124.5(3) . . . . ?
C5 C4 C9 O6 -56.4(4) . . . . ?
C4 C5 C10 O7 -67.5(4) . . . . ?
C4 C5 C10 O8 113.1(4) . . . . ?
C6 C5 C10 O7 115.6(4) . . . . ?
C6 C5 C10 O8 -63.8(4) . . . . ?
C1 C7 O2 Cu1 169.8(2) . . . . ?
O1 C7 O2 Cu1 -14.3(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O6 0.87(5) 2.31(5) 3.161(4) 166(4) 2_747
N1 H1B O4 0.88(5) 2.16(5) 3.034(4) 174(4) .
N1 H1C O1 0.78(5) 2.59(5) 3.210(4) 138(4) 3_667
N2 H2A O3 0.81(5) 2.21(5) 2.963(4) 154(4) 3_667
N2 H2A O9 0.81(5) 2.65(4) 3.067(4) 114(4) .
N2 H2B O8 0.95(5) 2.19(5) 3.128(4) 167(4) 3_767
N2 H2C O7 0.85(5) 2.29(5) 3.017(4) 144(4) 2_746
N3 H3A O7 0.87(4) 2.13(4) 3.000(4) 173(4) 2_746
N3 H3B O5 0.86(4) 2.04(4) 2.885(4) 166(4) 4_575
N3 H3C O2 0.84(4) 2.64(4) 3.063(4) 113(3) 3_767
N3 H3C O4 0.84(4) 2.29(5) 3.107(4) 166(4) 3_767
N4 H4A O7 0.85(5) 2.14(5) 2.980(4) 171(4) 2_746
N4 H4B O5 0.89(5) 2.23(5) 3.054(4) 154(4) 4_575
N5 H5A O8 0.83(5) 2.60(5) 3.297(4) 142(4) 4_475
N5 H5B O5 0.80(5) 2.27(5) 3.011(4) 154(4) 4_575
N5 H5C O3 0.88(5) 2.31(5) 3.177(4) 166(4) 1_554
N6 H6A O1 0.89(5) 1.94(5) 2.822(4) 171(4) 4_576
N6 H6B O8 0.93(5) 1.85(5) 2.767(5) 170(4) 4_476
N6 H6C O3 0.78(5) 2.01(5) 2.769(4) 164(5) .
N6 H6D O6 0.82(5) 2.05(5) 2.814(4) 157(4) 1_455
O9 H9A O4 0.77(5) 2.04(5) 2.800(4) 168(5) 3_667
O9 H9B O1 0.80(5) 1.92(5) 2.701(4) 162(4) .

_refine_diff_density_max         0.650
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.108

_exptl_crystal_recrystallization_method 
'Obtained direct from slow diffusion synthesis'
####################################################################### 
# 
# 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_wc48
_database_code_depnum_ccdc_archive 'CCDC 1044124'
_audit_update_record             
;
2015-01-16 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H26 Cu2 N4 O10,4 H2 O'
_chemical_formula_sum            'C30 H34 Cu2 N4 O14'
_chemical_formula_weight         801.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9464(9)
_cell_length_b                   11.1622(11)
_cell_length_c                   17.4780(17)
_cell_angle_alpha                82.360(2)
_cell_angle_beta                 81.293(2)
_cell_angle_gamma                82.365(2)
_cell_volume                     1698.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    4519
_cell_measurement_theta_min      2.313
_cell_measurement_theta_max      28.407

_exptl_crystal_description       Block
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.326
_shelx_estimated_absorpt_T_min   0.777
_shelx_estimated_absorpt_T_max   0.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.780
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker SMART 1K CCD diffractometer'
_diffrn_measurement_method       'narrow-frame ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12220
_diffrn_reflns_av_unetI/netI     0.1621
_diffrn_reflns_av_R_equivalents  0.0873
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.853
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             5926
_reflns_number_gt                3285
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'local programs'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  SHELXL-2014/7
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_extinction_coef       0.0032(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5926
_refine_ls_number_parameters     488
_refine_ls_number_restraints     438
_refine_ls_R_factor_all          0.1394
_refine_ls_R_factor_gt           0.0638
_refine_ls_wR_factor_ref         0.1489
_refine_ls_wR_factor_gt          0.1210
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.28804(10) 0.71317(8) 0.27010(5) 0.0114(3) Uani 1 1 d . U . . .
Cu2 Cu 0.74348(10) 0.30428(8) 0.26723(5) 0.0089(3) Uani 1 1 d . U . . .
C1 C 0.4934(8) 0.5468(6) 0.0714(4) 0.0069(15) Uani 1 1 d . U . . .
C2 C 0.5425(8) 0.4233(6) 0.0653(4) 0.0077(14) Uani 1 1 d . U . . .
C3 C 0.5470(7) 0.3784(6) -0.0058(4) 0.0085(15) Uani 1 1 d . U . . .
H3 H 0.5785 0.2944 -0.0095 0.010 Uiso 1 1 calc R U . . .
C4 C 0.4815(8) 0.6065(6) 0.1460(4) 0.0081(15) Uani 1 1 d . U . . .
C5 C 0.5978(8) 0.3354(6) 0.1313(4) 0.0084(15) Uani 1 1 d . U . . .
O1 O 0.5837(6) 0.6652(4) 0.1527(3) 0.0141(12) Uani 1 1 d . U . . .
O2 O 0.3555(5) 0.5999(4) 0.1912(3) 0.0104(11) Uani 1 1 d . U . . .
O3 O 0.6298(6) 0.2269(4) 0.1230(3) 0.0216(13) Uani 1 1 d . U . . .
O4 O 0.6053(5) 0.3832(4) 0.1933(3) 0.0111(11) Uani 1 1 d . U . . .
C6 C 0.0350(8) 0.9300(6) 0.4368(4) 0.0063(14) Uani 1 1 d . U . . .
C7 C -0.0302(8) 1.0510(6) 0.4251(4) 0.0080(15) Uani 1 1 d . U . . .
C8 C -0.0617(7) 1.1189(6) 0.4880(4) 0.0066(15) Uani 1 1 d . U . . .
H8 H -0.1030 1.2018 0.4796 0.008 Uiso 1 1 calc R U . . .
C9 C 0.0697(9) 0.8445(6) 0.3739(4) 0.0106(15) Uani 1 1 d . U . . .
C10 C -0.0655(8) 1.1090(6) 0.3454(4) 0.0094(15) Uani 1 1 d . U . . .
O5 O -0.0319(6) 0.7851(4) 0.3643(3) 0.0133(12) Uani 1 1 d . U . . .
O6 O 0.2088(6) 0.8327(4) 0.3432(3) 0.0161(12) Uani 1 1 d . U . . .
O7 O -0.0413(6) 1.0454(4) 0.2913(3) 0.0171(12) Uani 1 1 d . U . . .
O8 O -0.1210(5) 1.2204(4) 0.3412(3) 0.0117(11) Uani 1 1 d . U . . .
N1 N 0.2830(7) 0.8476(5) 0.1822(3) 0.0132(14) Uani 1 1 d . U . . .
C11 C 0.1917(9) 0.8484(8) 0.1290(5) 0.027(2) Uani 1 1 d . U . . .
H11 H 0.1221 0.7893 0.1363 0.032 Uiso 1 1 calc R U . . .
C12 C 0.1948(11) 0.9337(8) 0.0626(5) 0.035(2) Uani 1 1 d . U . . .
H12 H 0.1302 0.9309 0.0246 0.043 Uiso 1 1 calc R U . . .
C13 C 0.2910(11) 1.0202(8) 0.0530(5) 0.035(2) Uani 1 1 d . U . . .
H13 H 0.2936 1.0799 0.0088 0.042 Uiso 1 1 calc R U . . .
C14 C 0.3842(10) 1.0201(7) 0.1082(5) 0.030(2) Uani 1 1 d . U . . .
H14 H 0.4526 1.0798 0.1025 0.036 Uiso 1 1 calc R U . . .
C15 C 0.3788(9) 0.9338(7) 0.1718(5) 0.0207(18) Uani 1 1 d . U . . .
H15 H 0.4445 0.9347 0.2096 0.025 Uiso 1 1 calc R U . . .
N2 N 0.2515(7) 0.5747(5) 0.3519(3) 0.0131(14) Uani 1 1 d . U . . .
C16 C 0.1846(9) 0.4803(7) 0.3374(5) 0.0186(18) Uani 1 1 d . U . . .
H16 H 0.1683 0.4751 0.2855 0.022 Uiso 1 1 calc R U . . .
C17 C 0.1384(9) 0.3903(7) 0.3960(5) 0.024(2) Uani 1 1 d . U . . .
H17 H 0.0874 0.3267 0.3846 0.029 Uiso 1 1 calc R U . . .
C18 C 0.1681(10) 0.3947(8) 0.4716(5) 0.027(2) Uani 1 1 d . U . . .
H18 H 0.1398 0.3334 0.5124 0.033 Uiso 1 1 calc R U . . .
C19 C 0.2388(9) 0.4892(7) 0.4857(5) 0.0231(19) Uani 1 1 d . U . . .
H19 H 0.2599 0.4952 0.5366 0.028 Uiso 1 1 calc R U . . .
C20 C 0.2790(9) 0.5756(7) 0.4248(4) 0.0170(17) Uani 1 1 d . U . . .
H20 H 0.3295 0.6400 0.4353 0.020 Uiso 1 1 calc R U . . .
N3 N 0.9191(7) 0.3546(5) 0.1879(3) 0.0117(14) Uani 1 1 d . U . . .
C21 C 1.0522(9) 0.2861(7) 0.1751(5) 0.0211(19) Uani 1 1 d . U . . .
H21 H 1.0663 0.2087 0.2048 0.025 Uiso 1 1 calc R U . . .
C22 C 1.1697(9) 0.3227(7) 0.1208(5) 0.027(2) Uani 1 1 d . U . . .
H22 H 1.2619 0.2702 0.1122 0.032 Uiso 1 1 calc R U . . .
C23 C 1.1531(9) 0.4361(7) 0.0788(4) 0.0189(18) Uani 1 1 d . U . . .
H23 H 1.2332 0.4639 0.0413 0.023 Uiso 1 1 calc R U . . .
C24 C 1.0167(8) 0.5076(7) 0.0929(4) 0.0152(17) Uani 1 1 d . U . . .
H24 H 1.0006 0.5862 0.0650 0.018 Uiso 1 1 calc R U . . .
C25 C 0.9043(8) 0.4646(6) 0.1476(4) 0.0119(16) Uani 1 1 d . U . . .
H25 H 0.8112 0.5155 0.1573 0.014 Uiso 1 1 calc R U . . .
N4 N 0.5711(7) 0.2304(5) 0.3371(3) 0.0152(14) Uani 1 1 d . U . . .
C26 C 0.4724(8) 0.1710(7) 0.3117(5) 0.0194(18) Uani 1 1 d . U . . .
H26 H 0.4741 0.1738 0.2570 0.023 Uiso 1 1 calc R U . . .
C27 C 0.3676(9) 0.1054(8) 0.3600(5) 0.028(2) Uani 1 1 d . U . . .
H27 H 0.3000 0.0635 0.3393 0.034 Uiso 1 1 calc R U . . .
C28 C 0.3643(9) 0.1028(7) 0.4388(5) 0.0264(19) Uani 1 1 d . U . . .
H28 H 0.2942 0.0578 0.4737 0.032 Uiso 1 1 calc R U . . .
C29 C 0.4615(9) 0.1649(8) 0.4675(5) 0.029(2) Uani 1 1 d . U . . .
H29 H 0.4598 0.1638 0.5220 0.035 Uiso 1 1 calc R U . . .
C30 C 0.5621(9) 0.2291(8) 0.4152(4) 0.0222(19) Uani 1 1 d . U . . .
H30 H 0.6277 0.2742 0.4348 0.027 Uiso 1 1 calc R U . . .
O9 O 0.5283(6) 0.7067(5) 0.3023(3) 0.0200(13) Uani 1 1 d D U . . .
H9A H 0.552(8) 0.715(6) 0.2538(8) 0.030 Uiso 1 1 d D U . . .
H9B H 0.557(8) 0.766(4) 0.319(3) 0.030 Uiso 1 1 d D U . . .
O10 O 0.7262(6) 0.4790(4) 0.3251(3) 0.0169(12) Uani 1 1 d D U . . .
H10A H 0.794(5) 0.525(5) 0.311(4) 0.025 Uiso 1 1 d D U . . .
H10B H 0.643(3) 0.519(5) 0.316(4) 0.025 Uiso 1 1 d D U . . .
O11 O 0.9357(8) 0.6411(5) 0.2561(3) 0.0321(15) Uani 1 1 d D . . . .
H11A H 0.962(10) 0.691(5) 0.282(4) 0.048 Uiso 1 1 d D U . . .
H11B H 0.905(10) 0.680(5) 0.216(3) 0.048 Uiso 1 1 d D U . . .
O12 O 0.7684(7) 1.0131(5) 0.1895(4) 0.0309(16) Uani 1 1 d D . . . .
H12A H 0.736(9) 1.076(4) 0.162(4) 0.046 Uiso 1 1 d D U . . .
H12B H 0.821(8) 1.037(6) 0.220(4) 0.046 Uiso 1 1 d D U . . .
O13 O 0.8371(6) 0.7964(5) 0.1209(4) 0.0283(15) Uani 1 1 d D . . . .
H13A H 0.750(4) 0.778(6) 0.119(5) 0.042 Uiso 1 1 d D U . . .
H13B H 0.826(7) 0.856(5) 0.146(4) 0.042 Uiso 1 1 d D U . . .
O14 O 0.6715(6) 0.8856(5) 0.3447(3) 0.0252(14) Uani 1 1 d D . . . .
H14A H 0.753(4) 0.842(5) 0.353(5) 0.038 Uiso 1 1 d D U . . .
H14B H 0.696(7) 0.948(4) 0.316(4) 0.038 Uiso 1 1 d D U . . .


_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 1.968(5) . ?
Cu1 O6 1.960(5) . ?
Cu1 N1 2.002(6) . ?
Cu1 N2 1.986(6) . ?
Cu1 O9 2.293(6) . ?
Cu2 O4 1.966(5) . ?
Cu2 O8 1.968(5) 1_645 ?
Cu2 N3 2.019(6) . ?
Cu2 N4 2.012(6) . ?
Cu2 O10 2.290(5) . ?
C1 C2 1.403(9) . ?
C1 C3 1.391(9) 2_665 ?
C1 C4 1.525(9) . ?
C2 C3 1.393(9) . ?
C2 C5 1.510(9) . ?
C3 C1 1.391(9) 2_665 ?
C3 H3 0.950 . ?
C4 O1 1.221(8) . ?
C4 O2 1.280(8) . ?
C5 O3 1.230(8) . ?
C5 O4 1.284(8) . ?
C6 C7 1.400(9) . ?
C6 C8 1.397(9) 2_576 ?
C6 C9 1.521(9) . ?
C7 C8 1.391(9) . ?
C7 C10 1.517(9) . ?
C8 C6 1.397(9) 2_576 ?
C8 H8 0.950 . ?
C9 O5 1.237(8) . ?
C9 O6 1.275(8) . ?
C10 O7 1.233(8) . ?
C10 O8 1.273(8) . ?
O8 Cu2 1.967(5) 1_465 ?
N1 C11 1.325(9) . ?
N1 C15 1.348(9) . ?
C11 H11 0.950 . ?
C11 C12 1.400(11) . ?
C12 H12 0.950 . ?
C12 C13 1.355(12) . ?
C13 H13 0.950 . ?
C13 C14 1.367(11) . ?
C14 H14 0.950 . ?
C14 C15 1.370(10) . ?
C15 H15 0.950 . ?
N2 C16 1.348(9) . ?
N2 C20 1.335(9) . ?
C16 H16 0.950 . ?
C16 C17 1.392(10) . ?
C17 H17 0.950 . ?
C17 C18 1.395(10) . ?
C18 H18 0.950 . ?
C18 C19 1.367(11) . ?
C19 H19 0.950 . ?
C19 C20 1.377(10) . ?
C20 H20 0.950 . ?
N3 C21 1.333(9) . ?
N3 C25 1.332(9) . ?
C21 H21 0.950 . ?
C21 C22 1.372(10) . ?
C22 H22 0.950 . ?
C22 C23 1.379(10) . ?
C23 H23 0.950 . ?
C23 C24 1.375(10) . ?
C24 H24 0.950 . ?
C24 C25 1.368(10) . ?
C25 H25 0.950 . ?
N4 C26 1.330(9) . ?
N4 C30 1.353(9) . ?
C26 H26 0.950 . ?
C26 C27 1.381(10) . ?
C27 H27 0.950 . ?
C27 C28 1.369(11) . ?
C28 H28 0.950 . ?
C28 C29 1.368(12) . ?
C29 H29 0.950 . ?
C29 C30 1.381(10) . ?
C30 H30 0.950 . ?
O9 H9A 0.837(10) . ?
O9 H9B 0.839(10) . ?
O10 H10A 0.839(10) . ?
O10 H10B 0.839(10) . ?
O11 H11A 0.838(10) . ?
O11 H11B 0.838(10) . ?
O12 H12A 0.842(10) . ?
O12 H12B 0.841(10) . ?
O13 H13A 0.841(10) . ?
O13 H13B 0.838(10) . ?
O14 H14A 0.841(10) . ?
O14 H14B 0.841(10) . ?

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 O6 175.4(2) . . ?
O2 Cu1 N1 87.4(2) . . ?
O2 Cu1 N2 90.6(2) . . ?
O2 Cu1 O9 92.95(19) . . ?
O6 Cu1 N1 89.2(2) . . ?
O6 Cu1 N2 92.1(2) . . ?
O6 Cu1 O9 90.9(2) . . ?
N1 Cu1 N2 168.2(3) . . ?
N1 Cu1 O9 102.8(2) . . ?
N2 Cu1 O9 88.9(2) . . ?
O4 Cu2 O8 178.2(2) . 1_645 ?
O4 Cu2 N3 88.1(2) . . ?
O4 Cu2 N4 91.2(2) . . ?
O4 Cu2 O10 91.44(19) . . ?
O8 Cu2 N3 92.9(2) 1_645 . ?
O8 Cu2 N4 87.5(2) 1_645 . ?
O8 Cu2 O10 90.09(19) 1_645 . ?
N3 Cu2 N4 170.7(3) . . ?
N3 Cu2 O10 92.0(2) . . ?
N4 Cu2 O10 97.2(2) . . ?
C2 C1 C3 118.9(6) . 2_665 ?
C2 C1 C4 124.3(6) . . ?
C3 C1 C4 116.7(6) 2_665 . ?
C1 C2 C3 119.3(6) . . ?
C1 C2 C5 123.5(6) . . ?
C3 C2 C5 117.1(6) . . ?
C1 C3 C2 121.7(7) 2_665 . ?
C1 C3 H3 119.1 2_665 . ?
C2 C3 H3 119.1 . . ?
C1 C4 O1 117.7(6) . . ?
C1 C4 O2 115.0(6) . . ?
O1 C4 O2 126.9(7) . . ?
C2 C5 O3 119.6(6) . . ?
C2 C5 O4 115.0(6) . . ?
O3 C5 O4 125.4(6) . . ?
Cu1 O2 C4 121.2(4) . . ?
Cu2 O4 C5 120.3(4) . . ?
C7 C6 C8 118.5(6) . 2_576 ?
C7 C6 C9 124.3(6) . . ?
C8 C6 C9 117.0(6) 2_576 . ?
C6 C7 C8 119.0(6) . . ?
C6 C7 C10 121.3(6) . . ?
C8 C7 C10 119.8(6) . . ?
C6 C8 C7 122.5(6) 2_576 . ?
C6 C8 H8 118.7 2_576 . ?
C7 C8 H8 118.7 . . ?
C6 C9 O5 118.1(6) . . ?
C6 C9 O6 114.2(6) . . ?
O5 C9 O6 127.2(7) . . ?
C7 C10 O7 118.3(6) . . ?
C7 C10 O8 115.8(6) . . ?
O7 C10 O8 125.9(7) . . ?
Cu1 O6 C9 122.1(5) . . ?
Cu2 O8 C10 126.4(4) 1_465 . ?
Cu1 N1 C11 119.9(5) . . ?
Cu1 N1 C15 121.7(5) . . ?
C11 N1 C15 118.2(7) . . ?
N1 C11 H11 119.0 . . ?
N1 C11 C12 122.0(8) . . ?
H11 C11 C12 119.0 . . ?
C11 C12 H12 120.4 . . ?
C11 C12 C13 119.3(8) . . ?
H12 C12 C13 120.4 . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.7(8) . . ?
H13 C13 C14 120.6 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.0(8) . . ?
H14 C14 C15 120.0 . . ?
N1 C15 C14 121.8(8) . . ?
N1 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
Cu1 N2 C16 120.7(5) . . ?
Cu1 N2 C20 122.0(5) . . ?
C16 N2 C20 117.0(7) . . ?
N2 C16 H16 118.9 . . ?
N2 C16 C17 122.1(7) . . ?
H16 C16 C17 118.9 . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.1(8) . . ?
H17 C17 C18 120.4 . . ?
C17 C18 H18 120.8 . . ?
C17 C18 C19 118.5(8) . . ?
H18 C18 C19 120.8 . . ?
C18 C19 H19 120.6 . . ?
C18 C19 C20 118.9(8) . . ?
H19 C19 C20 120.6 . . ?
N2 C20 C19 124.3(8) . . ?
N2 C20 H20 117.9 . . ?
C19 C20 H20 117.9 . . ?
Cu2 N3 C21 123.9(5) . . ?
Cu2 N3 C25 118.5(5) . . ?
C21 N3 C25 117.5(7) . . ?
N3 C21 H21 118.7 . . ?
N3 C21 C22 122.7(7) . . ?
H21 C21 C22 118.7 . . ?
C21 C22 H22 120.2 . . ?
C21 C22 C23 119.5(8) . . ?
H22 C22 C23 120.2 . . ?
C22 C23 H23 121.1 . . ?
C22 C23 C24 117.8(7) . . ?
H23 C23 C24 121.1 . . ?
C23 C24 H24 120.3 . . ?
C23 C24 C25 119.4(7) . . ?
H24 C24 C25 120.3 . . ?
N3 C25 C24 123.1(7) . . ?
N3 C25 H25 118.4 . . ?
C24 C25 H25 118.4 . . ?
Cu2 N4 C26 123.6(5) . . ?
Cu2 N4 C30 119.2(5) . . ?
C26 N4 C30 116.8(7) . . ?
N4 C26 H26 118.0 . . ?
N4 C26 C27 124.0(8) . . ?
H26 C26 C27 118.0 . . ?
C26 C27 H27 121.1 . . ?
C26 C27 C28 117.8(8) . . ?
H27 C27 C28 121.1 . . ?
C27 C28 H28 119.9 . . ?
C27 C28 C29 120.2(8) . . ?
H28 C28 C29 119.9 . . ?
C28 C29 H29 120.8 . . ?
C28 C29 C30 118.4(8) . . ?
H29 C29 C30 120.8 . . ?
N4 C30 C29 122.7(8) . . ?
N4 C30 H30 118.6 . . ?
C29 C30 H30 118.6 . . ?
Cu1 O9 H9A 82(5) . . ?
Cu1 O9 H9B 122(5) . . ?
H9A O9 H9B 107.4(18) . . ?
Cu2 O10 H10A 119(5) . . ?
Cu2 O10 H10B 106(5) . . ?
H10A O10 H10B 107.5(18) . . ?
H11A O11 H11B 107.6(18) . . ?
H12A O12 H12B 106.4(18) . . ?
H13A O13 H13B 107.2(18) . . ?
H14A O14 H14B 106.6(18) . . ?

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
C3 C1 C2 C3 -1.1(11) 2_665 . . . ?
C3 C1 C2 C5 176.3(6) 2_665 . . . ?
C4 C1 C2 C3 179.2(6) . . . . ?
C4 C1 C2 C5 -3.4(11) . . . . ?
C1 C2 C3 C1 1.2(11) . . . 2_665 ?
C5 C2 C3 C1 -176.4(6) . . . 2_665 ?
C2 C1 C4 O1 100.6(8) . . . . ?
C2 C1 C4 O2 -86.6(8) . . . . ?
C3 C1 C4 O1 -79.0(8) 2_665 . . . ?
C3 C1 C4 O2 93.7(7) 2_665 . . . ?
C1 C2 C5 O3 175.4(7) . . . . ?
C1 C2 C5 O4 -3.7(10) . . . . ?
C3 C2 C5 O3 -7.2(10) . . . . ?
C3 C2 C5 O4 173.7(6) . . . . ?
C1 C4 O2 Cu1 -159.3(4) . . . . ?
O1 C4 O2 Cu1 12.6(10) . . . . ?
C2 C5 O4 Cu2 -156.0(4) . . . . ?
O3 C5 O4 Cu2 24.9(10) . . . . ?
C8 C6 C7 C8 1.9(11) 2_576 . . . ?
C8 C6 C7 C10 -178.7(6) 2_576 . . . ?
C9 C6 C7 C8 177.7(6) . . . . ?
C9 C6 C7 C10 -2.9(11) . . . . ?
C6 C7 C8 C6 -2.0(11) . . . 2_576 ?
C10 C7 C8 C6 178.6(6) . . . 2_576 ?
C7 C6 C9 O5 -87.8(9) . . . . ?
C7 C6 C9 O6 99.9(8) . . . . ?
C8 C6 C9 O5 88.0(8) 2_576 . . . ?
C8 C6 C9 O6 -84.2(8) 2_576 . . . ?
C6 C7 C10 O7 3.0(10) . . . . ?
C6 C7 C10 O8 -178.3(6) . . . . ?
C8 C7 C10 O7 -177.5(7) . . . . ?
C8 C7 C10 O8 1.2(10) . . . . ?
C6 C9 O6 Cu1 172.5(4) . . . . ?
O5 C9 O6 Cu1 1.1(10) . . . . ?
C7 C10 O8 Cu2 -152.1(5) . . . 1_465 ?
O7 C10 O8 Cu2 26.5(11) . . . 1_465 ?
Cu1 N1 C11 C12 -173.8(7) . . . . ?
C15 N1 C11 C12 1.4(12) . . . . ?
N1 C11 C12 C13 -1.8(14) . . . . ?
C11 C12 C13 C14 1.1(14) . . . . ?
C12 C13 C14 C15 -0.2(14) . . . . ?
Cu1 N1 C15 C14 174.6(6) . . . . ?
C11 N1 C15 C14 -0.4(11) . . . . ?
C13 C14 C15 N1 -0.2(13) . . . . ?
Cu1 N2 C16 C17 -171.0(6) . . . . ?
C20 N2 C16 C17 3.2(11) . . . . ?
N2 C16 C17 C18 -2.8(12) . . . . ?
C16 C17 C18 C19 1.4(12) . . . . ?
C17 C18 C19 C20 -0.5(12) . . . . ?
Cu1 N2 C20 C19 171.8(6) . . . . ?
C16 N2 C20 C19 -2.3(11) . . . . ?
C18 C19 C20 N2 1.0(12) . . . . ?
Cu2 N3 C21 C22 -179.9(6) . . . . ?
C25 N3 C21 C22 -2.5(11) . . . . ?
N3 C21 C22 C23 1.9(13) . . . . ?
C21 C22 C23 C24 -0.7(12) . . . . ?
C22 C23 C24 C25 0.2(11) . . . . ?
Cu2 N3 C25 C24 179.6(5) . . . . ?
C21 N3 C25 C24 2.0(10) . . . . ?
C23 C24 C25 N3 -0.9(11) . . . . ?
Cu2 N4 C26 C27 170.4(6) . . . . ?
C30 N4 C26 C27 -2.7(11) . . . . ?
N4 C26 C27 C28 0.8(12) . . . . ?
C26 C27 C28 C29 0.7(12) . . . . ?
C27 C28 C29 C30 -0.2(12) . . . . ?
Cu2 N4 C30 C29 -170.2(6) . . . . ?
C26 N4 C30 C29 3.2(11) . . . . ?
C28 C29 C30 N4 -1.9(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O9 H9A O1 0.837(10) 1.89(3) 2.678(7) 155(6) .
O9 H9B O14 0.839(10) 1.93(2) 2.746(8) 165(7) .
O10 H10A O11 0.839(10) 1.98(2) 2.806(8) 167(7) .
O10 H10B O9 0.839(10) 2.21(4) 2.916(7) 142(6) .
O11 H11A O5 0.838(10) 1.90(3) 2.709(7) 161(8) 1_655
O11 H11B O13 0.838(10) 2.082(17) 2.916(9) 173(7) .
O12 H12A O3 0.842(10) 1.92(3) 2.738(7) 165(9) 1_565
O12 H12B O7 0.841(10) 1.91(2) 2.729(7) 165(7) 1_655
O13 H13A O1 0.841(10) 2.04(4) 2.807(7) 151(8) .
O13 H13B O12 0.838(10) 1.97(2) 2.796(8) 168(8) .
O14 H14A O5 0.841(10) 1.98(2) 2.793(7) 163(6) 1_655
O14 H14B O7 0.841(10) 2.67(5) 3.272(7) 130(5) 1_655
O14 H14B O12 0.841(10) 2.25(5) 2.954(8) 141(7) .

_refine_diff_density_max         0.754
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.142

_exptl_crystal_recrystallization_method 
'Obtained direct from slow diffusion synthesis'
####################################################################### 
# 
# 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_jmh3
_database_code_depnum_ccdc_archive 'CCDC 1044125'
_audit_update_record             
;
2015-01-16 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H34 Cu2 N4 O11'
_chemical_formula_sum            'C33 H34 Cu2 N4 O11'
_chemical_formula_weight         789.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7980(3)
_cell_length_b                   10.6480(4)
_cell_length_c                   19.1470(8)
_cell_angle_alpha                94.840(3)
_cell_angle_beta                 90.453(3)
_cell_angle_gamma                110.355(4)
_cell_volume                     1674.37(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7450
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      29.44

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_F_000             812
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.337
_shelx_estimated_absorpt_T_min   0.731
_shelx_estimated_absorpt_T_max   0.776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_T_max  0.79
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube with Enhance optics'
_diffrn_measurement_device_type  
'Oxford Diffraction Gemini A Ultra diffractomer'
_diffrn_measurement_method       'thick-slice ω scans'
_diffrn_detector_area_resol_mean 10.3968
_diffrn_reflns_number            13658
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.820
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             6640
_reflns_number_gt                4652
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  SHELXL-2014/7
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL and local programs'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0515P)²+0.5893P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6640
_refine_ls_number_parameters     472
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1039
_refine_ls_wR_factor_gt          0.0963
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.39681(5) 0.47379(4) 0.21811(2) 0.01463(12) Uani 1 1 d . . . . .
Cu2 Cu 0.5000 1.0000 0.0000 0.01935(16) Uani 1 2 d S . P . .
Cu3 Cu 1.0000 1.0000 0.5000 0.01349(14) Uani 1 2 d S . P . .
C1 C 0.1129(4) 0.5134(3) 0.05452(16) 0.0125(7) Uani 1 1 d . . . . .
C2 C 0.1475(4) 0.6072(3) 0.00472(16) 0.0124(7) Uani 1 1 d . . . . .
C3 C 0.0346(4) 0.5931(3) -0.04888(16) 0.0128(7) Uani 1 1 d . . . . .
H3 H 0.0583 0.6574 -0.0825 0.015 Uiso 1 1 calc R U . . .
C4 C 0.2260(4) 0.5332(3) 0.11720(17) 0.0145(7) Uani 1 1 d . . . . .
C5 C 0.3104(4) 0.7175(3) 0.00520(17) 0.0160(8) Uani 1 1 d . . . . .
O1 O 0.2650(3) 0.6404(2) 0.15486(12) 0.0201(6) Uani 1 1 d . . . . .
O2 O 0.2702(3) 0.4340(2) 0.12847(11) 0.0173(5) Uani 1 1 d . . . . .
O3 O 0.4331(3) 0.6852(2) 0.00251(13) 0.0223(6) Uani 1 1 d . . . . .
O4 O 0.3087(3) 0.8376(2) 0.00601(12) 0.0202(6) Uani 1 1 d . . . . .
C6 C 0.5081(4) 0.5355(3) 0.43083(16) 0.0101(7) Uani 1 1 d . . . . .
C7 C 0.6311(4) 0.6088(3) 0.48067(16) 0.0109(7) Uani 1 1 d . . . . .
C8 C 0.6197(4) 0.5717(3) 0.54912(16) 0.0112(7) Uani 1 1 d . . . . .
H8 H 0.7026 0.6220 0.5830 0.013 Uiso 1 1 calc R U . . .
C9 C 0.5004(4) 0.5749(3) 0.35753(16) 0.0128(7) Uani 1 1 d . . . . .
C10 C 0.7774(4) 0.7235(3) 0.46053(17) 0.0124(7) Uani 1 1 d . . . . .
O5 O 0.4900(3) 0.6842(2) 0.34764(12) 0.0204(6) Uani 1 1 d . . . . .
O6 O 0.4979(3) 0.4811(2) 0.30986(11) 0.0155(5) Uani 1 1 d . . . . .
O7 O 0.8296(3) 0.7153(2) 0.40084(12) 0.0178(5) Uani 1 1 d . . . . .
O8 O 0.8352(3) 0.8208(2) 0.50809(11) 0.0137(5) Uani 1 1 d . . . . .
N1 N 0.1853(3) 0.4259(3) 0.26872(14) 0.0184(7) Uani 1 1 d . . . . .
C11 C 0.1217(4) 0.5196(4) 0.29140(18) 0.0201(8) Uani 1 1 d . . . . .
H11A H 0.1707 0.6090 0.2791 0.024 Uiso 1 1 calc R U . . .
C12 C -0.0140(5) 0.4883(5) 0.3324(2) 0.0375(11) Uani 1 1 d . . . . .
H12 H -0.0563 0.5559 0.3485 0.045 Uiso 1 1 calc R U . . .
C13 C -0.0858(5) 0.3590(6) 0.3492(2) 0.0449(13) Uani 1 1 d . . . . .
H13 H -0.1799 0.3353 0.3764 0.054 Uiso 1 1 calc R U . . .
C14 C -0.0202(5) 0.2636(5) 0.3264(2) 0.0438(12) Uani 1 1 d . . . . .
H34 H -0.0673 0.1737 0.3383 0.053 Uiso 1 1 calc R U . . .
C15 C 0.1139(5) 0.2997(4) 0.2861(2) 0.0296(9) Uani 1 1 d . . . . .
H35 H 0.1577 0.2331 0.2700 0.036 Uiso 1 1 calc R U . . .
N2 N 0.6129(3) 0.5680(3) 0.17598(14) 0.0183(6) Uani 1 1 d . . . . .
C16 C 0.7507(4) 0.6214(4) 0.21576(19) 0.0262(9) Uani 1 1 d . . . . .
H36 H 0.7464 0.6111 0.2646 0.031 Uiso 1 1 calc R U . . .
C17 C 0.8972(4) 0.6898(4) 0.1890(2) 0.0285(9) Uani 1 1 d . . . . .
H37 H 0.9925 0.7238 0.2186 0.034 Uiso 1 1 calc R U . . .
C18 C 0.9049(5) 0.7089(4) 0.1186(2) 0.0285(9) Uani 1 1 d . . . . .
H38 H 1.0047 0.7577 0.0989 0.034 Uiso 1 1 calc R U . . .
C19 C 0.7649(5) 0.6558(4) 0.0777(2) 0.0256(9) Uani 1 1 d . . . . .
H39 H 0.7662 0.6674 0.0290 0.031 Uiso 1 1 calc R U . . .
C20 C 0.6233(4) 0.5859(4) 0.10741(18) 0.0201(8) Uani 1 1 d . . . . .
H20 H 0.5277 0.5482 0.0781 0.024 Uiso 1 1 calc R U . . .
N3 N 0.5962(3) 0.9811(3) 0.09453(15) 0.0188(6) Uani 1 1 d . . . . .
C21 C 0.5014(5) 0.9082(3) 0.14230(19) 0.0240(9) Uani 1 1 d . . . . .
H21 H 0.3877 0.8704 0.1324 0.029 Uiso 1 1 calc R U . . .
C22 C 0.5622(5) 0.8859(4) 0.2052(2) 0.0293(9) Uani 1 1 d . . . . .
H22 H 0.4917 0.8325 0.2372 0.035 Uiso 1 1 calc R U . . .
C23 C 0.7258(5) 0.9423(4) 0.2206(2) 0.0306(10) Uani 1 1 d . . . . .
H23 H 0.7706 0.9293 0.2636 0.037 Uiso 1 1 calc R U . . .
C24 C 0.8242(5) 1.0185(4) 0.1723(2) 0.0308(10) Uani 1 1 d . . . . .
H24 H 0.9378 1.0589 0.1817 0.037 Uiso 1 1 calc R U . . .
C25 C 0.7563(4) 1.0353(4) 0.11049(19) 0.0234(8) Uani 1 1 d . . . . .
H25 H 0.8253 1.0874 0.0777 0.028 Uiso 1 1 calc R U . . .
N4 N 0.8181(3) 1.0670(3) 0.47746(14) 0.0143(6) Uani 1 1 d . . . . .
C26 C 0.7013(4) 0.9998(4) 0.42802(18) 0.0180(8) Uani 1 1 d . . . . .
H26 H 0.7063 0.9201 0.4034 0.022 Uiso 1 1 calc R U . . .
C27 C 0.5748(4) 1.0422(4) 0.41174(19) 0.0224(8) Uani 1 1 d . . . . .
H27 H 0.4974 0.9945 0.3752 0.027 Uiso 1 1 calc R U . . .
C28 C 0.5620(4) 1.1538(4) 0.4488(2) 0.0260(9) Uani 1 1 d . . . . .
H28 H 0.4740 1.1829 0.4393 0.031 Uiso 1 1 calc R U . . .
C29 C 0.6794(4) 1.2232(4) 0.5002(2) 0.0255(9) Uani 1 1 d . . . . .
H29 H 0.6733 1.3008 0.5266 0.031 Uiso 1 1 calc R U . . .
C30 C 0.8058(4) 1.1780(4) 0.51239(18) 0.0197(8) Uani 1 1 d . . . . .
H30 H 0.8876 1.2274 0.5469 0.024 Uiso 1 1 calc R U . . .
O9 O 0.4124(3) 0.2568(3) 0.20193(13) 0.0312(7) Uani 1 1 d D . . . .
H9 H 0.389(5) 0.219(4) 0.1608(10) 0.047 Uiso 1 1 d D U . . .
C31 C 0.5554(7) 0.2414(5) 0.2302(3) 0.0617(17) Uani 1 1 d . . . . .
H31A H 0.5339 0.1462 0.2359 0.093 Uiso 1 1 calc R U . . .
H31B H 0.5860 0.2939 0.2759 0.093 Uiso 1 1 calc R U . . .
H31C H 0.6442 0.2734 0.1982 0.093 Uiso 1 1 calc R U . . .
O10 O 1.0131(3) 0.9579(3) 0.36899(14) 0.0281(6) Uani 1 1 d D . . . .
H10 H 0.952(4) 0.8794(19) 0.374(2) 0.042 Uiso 1 1 d D U . . .
C32 C 1.1553(5) 0.9772(4) 0.3318(2) 0.0335(10) Uani 1 1 d . . . . .
H32A H 1.1959 0.9041 0.3387 0.034(12) Uiso 1 1 calc R . . . .
H32B H 1.2377 1.0634 0.3491 0.053(14) Uiso 1 1 calc R . . . .
H32C H 1.1314 0.9775 0.2818 0.047(13) Uiso 1 1 calc R . . . .
O11 O 0.3504(3) 1.1345(3) 0.06634(13) 0.0247(6) Uani 1 1 d D . . . .
H11 H 0.405(4) 1.199(3) 0.0440(19) 0.037 Uiso 1 1 d D U . . .
C33 C 0.1815(4) 1.1049(4) 0.0573(2) 0.0324(10) Uani 1 1 d . . . . .
H33A H 0.1522 1.1779 0.0812 0.046(13) Uiso 1 1 calc R . . . .
H33B H 0.1230 1.0204 0.0773 0.050(14) Uiso 1 1 calc R . . . .
H33C H 0.1523 1.0960 0.0072 0.056(14) Uiso 1 1 calc R . . . .


_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 1.971(2) . ?
Cu1 O6 1.946(2) . ?
Cu1 N1 2.028(3) . ?
Cu1 N2 2.026(3) . ?
Cu1 O9 2.357(3) . ?
Cu2 O4 1.961(2) . ?
Cu2 O4 1.961(2) 2_675 ?
Cu2 N3 2.047(3) . ?
Cu2 N3 2.047(3) 2_675 ?
Cu3 O8 1.973(2) . ?
Cu3 O8 1.973(2) 2_776 ?
Cu3 N4 2.023(3) . ?
Cu3 N4 2.023(3) 2_776 ?
C1 C2 1.398(4) . ?
C1 C3 1.391(4) 2_565 ?
C1 C4 1.505(4) . ?
C2 C3 1.384(4) . ?
C2 C5 1.503(4) . ?
C3 C1 1.391(4) 2_565 ?
C3 H3 0.950 . ?
C4 O1 1.235(4) . ?
C4 O2 1.279(4) . ?
C5 O3 1.241(4) . ?
C5 O4 1.283(4) . ?
C6 C7 1.401(4) . ?
C6 C8 1.379(4) 2_666 ?
C6 C9 1.506(4) . ?
C7 C8 1.395(4) . ?
C7 C10 1.513(4) . ?
C8 C6 1.379(4) 2_666 ?
C8 H8 0.950 . ?
C9 O5 1.229(4) . ?
C9 O6 1.289(4) . ?
C10 O7 1.243(4) . ?
C10 O8 1.276(4) . ?
N1 C11 1.347(5) . ?
N1 C15 1.343(5) . ?
C11 H11A 0.950 . ?
C11 C12 1.392(5) . ?
C12 H12 0.950 . ?
C12 C13 1.368(7) . ?
C13 H13 0.950 . ?
C13 C14 1.376(7) . ?
C14 H34 0.950 . ?
C14 C15 1.372(6) . ?
C15 H35 0.950 . ?
N2 C16 1.344(4) . ?
N2 C20 1.342(4) . ?
C16 H36 0.950 . ?
C16 C17 1.369(5) . ?
C17 H37 0.950 . ?
C17 C18 1.379(5) . ?
C18 H38 0.950 . ?
C18 C19 1.369(5) . ?
C19 H39 0.950 . ?
C19 C20 1.366(5) . ?
C20 H20 0.950 . ?
N3 C21 1.348(4) . ?
N3 C25 1.344(4) . ?
C21 H21 0.950 . ?
C21 C22 1.385(5) . ?
C22 H22 0.950 . ?
C22 C23 1.371(6) . ?
C23 H23 0.950 . ?
C23 C24 1.384(6) . ?
C24 H24 0.950 . ?
C24 C25 1.374(5) . ?
C25 H25 0.950 . ?
N4 C26 1.350(4) . ?
N4 C30 1.346(4) . ?
C26 H26 0.950 . ?
C26 C27 1.380(5) . ?
C27 H27 0.950 . ?
C27 C28 1.371(5) . ?
C28 H28 0.950 . ?
C28 C29 1.383(5) . ?
C29 H29 0.950 . ?
C29 C30 1.382(5) . ?
C30 H30 0.950 . ?
O9 H9 0.842(10) . ?
O9 C31 1.432(5) . ?
C31 H31A 0.980 . ?
C31 H31B 0.980 . ?
C31 H31C 0.980 . ?
O10 H10 0.835(10) . ?
O10 C32 1.404(5) . ?
C32 H32A 0.980 . ?
C32 H32B 0.980 . ?
C32 H32C 0.980 . ?
O11 H11 0.841(10) . ?
O11 C33 1.413(5) . ?
C33 H33A 0.980 . ?
C33 H33B 0.980 . ?
C33 H33C 0.980 . ?

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 O6 169.89(10) . . ?
O2 Cu1 N1 88.60(10) . . ?
O2 Cu1 N2 95.07(10) . . ?
O2 Cu1 O9 88.33(9) . . ?
O6 Cu1 N1 85.60(10) . . ?
O6 Cu1 N2 92.53(10) . . ?
O6 Cu1 O9 84.32(9) . . ?
N1 Cu1 N2 166.01(12) . . ?
N1 Cu1 O9 98.16(11) . . ?
N2 Cu1 O9 95.44(11) . . ?
O4 Cu2 O4 180.0 . 2_675 ?
O4 Cu2 N3 92.69(10) . . ?
O4 Cu2 N3 87.31(10) . 2_675 ?
O4 Cu2 N3 92.69(10) 2_675 2_675 ?
O4 Cu2 N3 87.31(10) 2_675 . ?
N3 Cu2 N3 180.00(7) . 2_675 ?
O8 Cu3 O8 180.0 . 2_776 ?
O8 Cu3 N4 88.44(10) . . ?
O8 Cu3 N4 88.44(10) 2_776 2_776 ?
O8 Cu3 N4 91.56(10) . 2_776 ?
O8 Cu3 N4 91.56(10) 2_776 . ?
N4 Cu3 N4 180.0 . 2_776 ?
C2 C1 C3 119.1(3) . 2_565 ?
C2 C1 C4 120.8(3) . . ?
C3 C1 C4 119.8(3) 2_565 . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 C5 121.0(3) . . ?
C3 C2 C5 119.2(3) . . ?
C1 C3 C2 121.3(3) 2_565 . ?
C1 C3 H3 119.4 2_565 . ?
C2 C3 H3 119.4 . . ?
C1 C4 O1 118.6(3) . . ?
C1 C4 O2 116.5(3) . . ?
O1 C4 O2 124.9(3) . . ?
C2 C5 O3 118.1(3) . . ?
C2 C5 O4 116.0(3) . . ?
O3 C5 O4 125.8(3) . . ?
Cu1 O2 C4 109.6(2) . . ?
Cu2 O4 C5 125.3(2) . . ?
C7 C6 C8 118.9(3) . 2_666 ?
C7 C6 C9 123.1(3) . . ?
C8 C6 C9 117.7(3) 2_666 . ?
C6 C7 C8 118.9(3) . . ?
C6 C7 C10 120.9(3) . . ?
C8 C7 C10 120.1(3) . . ?
C6 C8 C7 122.1(3) 2_666 . ?
C6 C8 H8 118.9 2_666 . ?
C7 C8 H8 118.9 . . ?
C6 C9 O5 120.7(3) . . ?
C6 C9 O6 112.9(3) . . ?
O5 C9 O6 126.3(3) . . ?
C7 C10 O7 118.5(3) . . ?
C7 C10 O8 115.2(3) . . ?
O7 C10 O8 126.3(3) . . ?
Cu1 O6 C9 119.4(2) . . ?
Cu3 O8 C10 128.6(2) . . ?
Cu1 N1 C11 121.9(2) . . ?
Cu1 N1 C15 119.3(3) . . ?
C11 N1 C15 118.5(3) . . ?
N1 C11 H11A 119.3 . . ?
N1 C11 C12 121.5(4) . . ?
H11A C11 C12 119.3 . . ?
C11 C12 H12 120.4 . . ?
C11 C12 C13 119.2(4) . . ?
H12 C12 C13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.3(4) . . ?
H13 C13 C14 120.4 . . ?
C13 C14 H34 120.4 . . ?
C13 C14 C15 119.3(4) . . ?
H34 C14 C15 120.4 . . ?
N1 C15 C14 122.3(4) . . ?
N1 C15 H35 118.8 . . ?
C14 C15 H35 118.8 . . ?
Cu1 N2 C16 121.7(2) . . ?
Cu1 N2 C20 121.3(2) . . ?
C16 N2 C20 116.9(3) . . ?
N2 C16 H36 118.6 . . ?
N2 C16 C17 122.9(3) . . ?
H36 C16 C17 118.6 . . ?
C16 C17 H37 120.3 . . ?
C16 C17 C18 119.3(3) . . ?
H37 C17 C18 120.3 . . ?
C17 C18 H38 120.9 . . ?
C17 C18 C19 118.2(4) . . ?
H38 C18 C19 120.9 . . ?
C18 C19 H39 120.2 . . ?
C18 C19 C20 119.5(4) . . ?
H39 C19 C20 120.2 . . ?
N2 C20 C19 123.1(3) . . ?
N2 C20 H20 118.4 . . ?
C19 C20 H20 118.4 . . ?
Cu2 N3 C21 120.9(2) . . ?
Cu2 N3 C25 121.9(2) . . ?
C21 N3 C25 117.2(3) . . ?
N3 C21 H21 118.5 . . ?
N3 C21 C22 123.0(3) . . ?
H21 C21 C22 118.5 . . ?
C21 C22 H22 120.5 . . ?
C21 C22 C23 119.0(4) . . ?
H22 C22 C23 120.5 . . ?
C22 C23 H23 120.7 . . ?
C22 C23 C24 118.5(3) . . ?
H23 C23 C24 120.7 . . ?
C23 C24 H24 120.2 . . ?
C23 C24 C25 119.5(4) . . ?
H24 C24 C25 120.2 . . ?
N3 C25 C24 122.8(4) . . ?
N3 C25 H25 118.6 . . ?
C24 C25 H25 118.6 . . ?
Cu3 N4 C26 121.2(2) . . ?
Cu3 N4 C30 121.5(2) . . ?
C26 N4 C30 117.3(3) . . ?
N4 C26 H26 118.7 . . ?
N4 C26 C27 122.7(3) . . ?
H26 C26 C27 118.7 . . ?
C26 C27 H27 120.3 . . ?
C26 C27 C28 119.4(3) . . ?
H27 C27 C28 120.3 . . ?
C27 C28 H28 120.6 . . ?
C27 C28 C29 118.8(3) . . ?
H28 C28 C29 120.6 . . ?
C28 C29 H29 120.5 . . ?
C28 C29 C30 118.9(4) . . ?
H29 C29 C30 120.5 . . ?
N4 C30 C29 122.9(3) . . ?
N4 C30 H30 118.6 . . ?
C29 C30 H30 118.6 . . ?
Cu1 O9 H9 115(3) . . ?
Cu1 O9 C31 116.5(2) . . ?
H9 O9 C31 111(3) . . ?
O9 C31 H31A 109.5 . . ?
O9 C31 H31B 109.5 . . ?
O9 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
H10 O10 C32 119(3) . . ?
O10 C32 H32A 109.5 . . ?
O10 C32 H32B 109.5 . . ?
O10 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
H11 O11 C33 112(3) . . ?
O11 C33 H33A 109.5 . . ?
O11 C33 H33B 109.5 . . ?
O11 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

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
C3 C1 C2 C3 0.3(5) 2_565 . . . ?
C3 C1 C2 C5 -175.0(3) 2_565 . . . ?
C4 C1 C2 C3 -174.1(3) . . . . ?
C4 C1 C2 C5 10.6(5) . . . . ?
C1 C2 C3 C1 -0.3(5) . . . 2_565 ?
C5 C2 C3 C1 175.1(3) . . . 2_565 ?
C2 C1 C4 O1 53.6(4) . . . . ?
C2 C1 C4 O2 -128.7(3) . . . . ?
C3 C1 C4 O1 -120.8(3) 2_565 . . . ?
C3 C1 C4 O2 57.0(4) 2_565 . . . ?
C1 C2 C5 O3 55.6(4) . . . . ?
C1 C2 C5 O4 -126.7(3) . . . . ?
C3 C2 C5 O3 -119.7(4) . . . . ?
C3 C2 C5 O4 58.0(4) . . . . ?
C1 C4 O2 Cu1 -173.7(2) . . . . ?
O1 C4 O2 Cu1 3.9(4) . . . . ?
C2 C5 O4 Cu2 -175.4(2) . . . . ?
O3 C5 O4 Cu2 2.2(5) . . . . ?
C8 C6 C7 C8 -0.6(5) 2_666 . . . ?
C8 C6 C7 C10 177.4(3) 2_666 . . . ?
C9 C6 C7 C8 174.0(3) . . . . ?
C9 C6 C7 C10 -8.1(5) . . . . ?
C6 C7 C8 C6 0.6(5) . . . 2_666 ?
C10 C7 C8 C6 -177.4(3) . . . 2_666 ?
C7 C6 C9 O5 -60.1(5) . . . . ?
C7 C6 C9 O6 123.1(3) . . . . ?
C8 C6 C9 O5 114.4(3) 2_666 . . . ?
C8 C6 C9 O6 -62.3(4) 2_666 . . . ?
C6 C7 C10 O7 -33.7(4) . . . . ?
C6 C7 C10 O8 146.3(3) . . . . ?
C8 C7 C10 O7 144.2(3) . . . . ?
C8 C7 C10 O8 -35.8(4) . . . . ?
C6 C9 O6 Cu1 153.4(2) . . . . ?
O5 C9 O6 Cu1 -23.2(4) . . . . ?
C7 C10 O8 Cu3 -169.47(19) . . . . ?
O7 C10 O8 Cu3 10.5(5) . . . . ?
Cu1 N1 C11 C12 -173.1(3) . . . . ?
C15 N1 C11 C12 0.5(5) . . . . ?
N1 C11 C12 C13 -0.9(6) . . . . ?
C11 C12 C13 C14 1.3(6) . . . . ?
C12 C13 C14 C15 -1.2(6) . . . . ?
Cu1 N1 C15 C14 173.4(3) . . . . ?
C11 N1 C15 C14 -0.4(5) . . . . ?
C13 C14 C15 N1 0.8(6) . . . . ?
Cu1 N2 C16 C17 -177.5(3) . . . . ?
C20 N2 C16 C17 -0.8(6) . . . . ?
N2 C16 C17 C18 1.8(6) . . . . ?
C16 C17 C18 C19 -1.3(6) . . . . ?
C17 C18 C19 C20 -0.1(6) . . . . ?
Cu1 N2 C20 C19 176.0(3) . . . . ?
C16 N2 C20 C19 -0.7(5) . . . . ?
C18 C19 C20 N2 1.2(6) . . . . ?
Cu2 N3 C21 C22 176.1(3) . . . . ?
C25 N3 C21 C22 -1.1(5) . . . . ?
N3 C21 C22 C23 1.3(6) . . . . ?
C21 C22 C23 C24 -0.6(6) . . . . ?
C22 C23 C24 C25 -0.2(6) . . . . ?
Cu2 N3 C25 C24 -176.9(3) . . . . ?
C21 N3 C25 C24 0.3(5) . . . . ?
C23 C24 C25 N3 0.4(6) . . . . ?
Cu3 N4 C26 C27 179.5(3) . . . . ?
C30 N4 C26 C27 1.3(5) . . . . ?
N4 C26 C27 C28 -2.7(5) . . . . ?
C26 C27 C28 C29 1.9(5) . . . . ?
C27 C28 C29 C30 0.1(5) . . . . ?
Cu3 N4 C30 C29 -177.3(3) . . . . ?
C26 N4 C30 C29 0.8(5) . . . . ?
C28 C29 C30 N4 -1.6(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O9 H9 O11 0.842(10) 1.924(11) 2.765(4) 176(5) 1_545
O10 H10 O7 0.835(10) 1.826(13) 2.651(3) 169(4) .
O11 H11 O3 0.841(10) 1.825(16) 2.641(3) 163(4) 2_675

_refine_diff_density_max         0.554
_refine_diff_density_min         -0.836
_refine_diff_density_rms         0.091



_exptl_crystal_recrystallization_method 
'Obtained direct from slow diffusion synthesis'
