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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vk34l
_database_code_depnum_ccdc_archive 'CCDC 1023487'
_audit_update_record             
;
2015-06-10 deposited with the CCDC.
2016-03-24 downloaded from the CCDC.
;
_audit_creation_date             2015-04-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '0.24(C21 H17 N5 O4)'
_chemical_formula_sum            'C4.94 H4 N1.18 O0.94'
_chemical_formula_weight         94.92
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   10.4435(12)
_cell_length_b                   23.687(3)
_cell_length_c                   7.6810(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.110(3)
_cell_angle_gamma                90.00
_cell_volume                     1842.8(4)
_cell_formula_units_Z            17
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (sheldrick, 2003)'
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1493
_diffrn_reflns_av_unetI/netI     0.0705
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            82092
_diffrn_reflns_theta_full        28.42
_diffrn_reflns_theta_max         28.42
_diffrn_reflns_theta_min         2.65
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2588
_reflns_number_total             4604
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4604
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1335
_refine_ls_R_factor_gt           0.0596
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0394P)²+1.1572P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1277
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N4(H4), N2(H2), C15(H15), C10(H10), C2(H2A), C4(H4B), C7(H7), C19(H19),
 C3(H3), C12(H12), C1(H1A), C18(H18), C11(H11), C20(H20), C21(H21)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.49514(15) 0.65068(6) 0.3839(2) 0.0321(4) Uani 1 d . . .
H1 H 0.5407 0.6755 0.3549 0.048 Uiso 1 calc . . GR
O3 O 0.83226(16) 1.01242(6) 0.0210(2) 0.0383(4) Uani 1 d . . .
N3 N 0.77559(18) 0.87316(7) 0.1507(2) 0.0243(4) Uani 1 d . . .
N5 N 0.5815(2) 0.99923(7) -0.1685(2) 0.0283(5) Uani 1 d . . .
N4 N 0.65013(19) 0.95732(7) -0.0623(2) 0.0266(4) Uani 1 d . . .
H4 H 0.6132 0.9255 -0.0512 0.032 Uiso 1 calc . . R
O4 O 0.56446(18) 1.09777(7) -0.3280(2) 0.0432(5) Uani 1 d . . .
H4A H 0.6016 1.0718 -0.2648 0.065 Uiso 1 calc . . GR
O2 O 0.81099(17) 0.73793(7) 0.3561(3) 0.0441(5) Uani 1 d . . .
N1 N 0.54488(18) 0.74768(7) 0.2555(2) 0.0259(4) Uani 1 d . . .
N2 N 0.62930(18) 0.78842(7) 0.2237(3) 0.0272(5) Uani 1 d . . .
H2 H 0.5987 0.8190 0.1687 0.033 Uiso 1 calc . . R
C13 C 0.8477(2) 0.91766(9) 0.1254(3) 0.0262(5) Uani 1 d . . .
C16 C 0.3881(2) 1.02902(9) -0.3818(3) 0.0290(6) Uani 1 d . . .
C8 C 0.7605(2) 0.78026(9) 0.2789(3) 0.0292(5) Uani 1 d . . .
C15 C 0.4658(2) 0.98744(9) -0.2624(3) 0.0298(6) Uani 1 d . . .
H15 H 0.4309 0.9517 -0.2541 0.036 Uiso 1 calc . . R
C10 C 0.9756(2) 0.82907(10) 0.3108(3) 0.0331(6) Uani 1 d . . .
H10 H 1.0167 0.7979 0.3743 0.040 Uiso 1 calc . . R
C2 C 0.1005(2) 0.69497(11) 0.2516(3) 0.0380(6) Uani 1 d . . .
H2A H 0.0114 0.7045 0.2238 0.046 Uiso 1 calc . . R
C14 C 0.7772(2) 0.96716(9) 0.0245(3) 0.0282(5) Uani 1 d . . .
C4 C 0.2739(2) 0.62928(9) 0.3725(3) 0.0308(6) Uani 1 d . . .
H4B H 0.3008 0.5948 0.4269 0.037 Uiso 1 calc . . R
C7 C 0.4208(2) 0.76007(9) 0.2215(3) 0.0270(5) Uani 1 d . . .
H7 H 0.3918 0.7954 0.1753 0.032 Uiso 1 calc . . R
C9 C 0.8406(2) 0.82989(9) 0.2437(3) 0.0258(5) Uani 1 d . . .
C19 C 0.2355(3) 1.10580(11) -0.6193(3) 0.0428(7) Uani 1 d . . .
H19 H 0.1845 1.1315 -0.6984 0.051 Uiso 1 calc . . R
C17 C 0.4396(3) 1.08174(9) -0.4128(3) 0.0321(6) Uani 1 d . . .
C5 C 0.3662(2) 0.66600(9) 0.3339(3) 0.0263(5) Uani 1 d . . .
C6 C 0.3267(2) 0.71888(9) 0.2553(3) 0.0257(5) Uani 1 d . . .
C3 C 0.1428(2) 0.64366(10) 0.3308(3) 0.0337(6) Uani 1 d . . .
H3 H 0.0813 0.6185 0.3561 0.040 Uiso 1 calc . . R
C12 C 0.9836(2) 0.92031(10) 0.1880(3) 0.0337(6) Uani 1 d . . .
H12 H 1.0300 0.9520 0.1666 0.040 Uiso 1 calc . . R
C1 C 0.1936(2) 0.73205(10) 0.2141(3) 0.0340(6) Uani 1 d . . .
H1A H 0.1658 0.7665 0.1601 0.041 Uiso 1 calc . . R
C18 C 0.3630(3) 1.11922(10) -0.5339(3) 0.0393(7) Uani 1 d . . .
H18 H 0.3984 1.1536 -0.5571 0.047 Uiso 1 calc . . R
C11 C 1.0488(2) 0.87508(10) 0.2824(3) 0.0369(6) Uani 1 d . . .
H11 H 1.1401 0.8756 0.3260 0.044 Uiso 1 calc . . R
C20 C 0.1821(3) 1.05450(11) -0.5889(3) 0.0431(7) Uani 1 d . . .
H20 H 0.0953 1.0457 -0.6464 0.052 Uiso 1 calc . . R
C21 C 0.2584(3) 1.01647(10) -0.4730(3) 0.0369(6) Uani 1 d . . .
H21 H 0.2228 0.9816 -0.4549 0.044 Uiso 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
O1 C5 1.357(3) . ?
O3 C14 1.220(2) . ?
N3 C13 1.337(3) . ?
N3 C9 1.336(3) . ?
N5 N4 1.371(2) . ?
N5 C15 1.278(3) . ?
N4 C14 1.352(3) . ?
O4 C17 1.362(3) . ?
O2 C8 1.218(3) . ?
N1 N2 1.369(2) . ?
N1 C7 1.291(3) . ?
N2 C8 1.346(3) . ?
C13 C14 1.496(3) . ?
C13 C12 1.385(3) . ?
C16 C15 1.452(3) . ?
C16 C17 1.403(3) . ?
C16 C21 1.396(3) . ?
C8 C9 1.505(3) . ?
C10 C9 1.378(3) . ?
C10 C11 1.379(3) . ?
C2 C3 1.383(3) . ?
C2 C1 1.392(3) . ?
C4 C5 1.383(3) . ?
C4 C3 1.371(3) . ?
C7 C6 1.453(3) . ?
C19 C18 1.370(4) . ?
C19 C20 1.380(4) . ?
C17 C18 1.389(3) . ?
C5 C6 1.408(3) . ?
C6 C1 1.384(3) . ?
C12 C11 1.377(3) . ?
C20 C21 1.376(3) . ?

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
C9 N3 C13 116.85(19) . . ?
C15 N5 N4 117.56(19) . . ?
C14 N4 N5 118.45(18) . . ?
C7 N1 N2 117.49(18) . . ?
C8 N2 N1 119.53(18) . . ?
N3 C13 C14 118.0(2) . . ?
N3 C13 C12 123.5(2) . . ?
C12 C13 C14 118.5(2) . . ?
C17 C16 C15 122.2(2) . . ?
C21 C16 C15 119.8(2) . . ?
C21 C16 C17 118.0(2) . . ?
O2 C8 N2 124.0(2) . . ?
O2 C8 C9 122.5(2) . . ?
N2 C8 C9 113.52(19) . . ?
N5 C15 C16 121.0(2) . . ?
C9 C10 C11 119.1(2) . . ?
C3 C2 C1 118.8(2) . . ?
O3 C14 N4 123.5(2) . . ?
O3 C14 C13 121.7(2) . . ?
N4 C14 C13 114.85(18) . . ?
C3 C4 C5 120.1(2) . . ?
N1 C7 C6 120.0(2) . . ?
N3 C9 C8 117.6(2) . . ?
N3 C9 C10 123.4(2) . . ?
C10 C9 C8 119.0(2) . . ?
C18 C19 C20 120.6(2) . . ?
O4 C17 C16 122.0(2) . . ?
O4 C17 C18 118.0(2) . . ?
C18 C17 C16 120.0(2) . . ?
O1 C5 C4 117.83(19) . . ?
O1 C5 C6 121.72(19) . . ?
C4 C5 C6 120.3(2) . . ?
C5 C6 C7 122.3(2) . . ?
C1 C6 C7 119.6(2) . . ?
C1 C6 C5 118.1(2) . . ?
C4 C3 C2 121.0(2) . . ?
C11 C12 C13 118.7(2) . . ?
C6 C1 C2 121.6(2) . . ?
C19 C18 C17 120.4(2) . . ?
C12 C11 C10 118.4(2) . . ?
C21 C20 C19 119.4(3) . . ?
C20 C21 C16 121.5(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vb11
_database_code_depnum_ccdc_archive 'CCDC 1023488'
_audit_update_record             
;
2015-06-10 deposited with the CCDC.
2016-03-24 downloaded from the CCDC.
;
_audit_creation_date             2015-04-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H22 Cu3 N8 O12, 3(C3 H7 N O)'
_chemical_formula_sum            'C33 H43 Cu3 N11 O15'
_chemical_formula_weight         1024.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.9275(4)
_cell_length_b                   14.7056(8)
_cell_length_c                   16.2494(9)
_cell_angle_alpha                94.018(2)
_cell_angle_beta                 97.183(2)
_cell_angle_gamma                103.840(2)
_cell_volume                     2044.00(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    1.629
_exptl_absorpt_correction_T_max  0.521
_exptl_absorpt_correction_T_min  0.462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (sheldrick, 2003)'
_exptl_crystal_colour            'clear greenish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1050
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            68074
_diffrn_reflns_theta_full        28.58
_diffrn_reflns_theta_max         28.58
_diffrn_reflns_theta_min         2.38
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                9325
_reflns_number_total             10373
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         2.006
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     575
_refine_ls_number_reflns         10373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0301
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0420P)²+2.4730P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0825
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C17(H17), C19(H19), C25(H25), C11(H11), C10(H10), C31(H31),
 C20(H20), C18(H18), C15(H15), C28(H28), C7(H7), C2(H2), C1(H1), C4(H4), C3(H3),
  C22(H22)
2.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C33(H33A,H33B,H33C), C30(H30A,H30B,H30C), C27(H27A,H27B,
 H27C), C29(H29A,H29B,H29C), C32(H32A,H32B,H32C), C23(H23A,H23B,H23C), C24(H24A,
 H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cu1 Cu 0.26639(2) 0.243937(15) 0.238345(13) 0.01147(6) Uani 1 d . . .
Cu2 Cu 0.01864(2) 0.436354(15) 0.066173(13) 0.01147(6) Uani 1 d . . .
Cu3 Cu 0.38911(2) 0.042248(15) 0.446633(13) 0.01220(6) Uani 1 d . . .
O4 O 0.12282(15) 0.48753(9) -0.02490(8) 0.0141(2) Uani 1 d . . .
O3 O -0.05842(15) 0.38912(9) 0.16693(8) 0.0151(3) Uani 1 d . . .
O6 O 0.35915(16) 0.18841(9) 0.14567(8) 0.0157(3) Uani 1 d . . .
O9 O 0.50481(16) 0.33207(10) 0.26993(9) 0.0202(3) Uani 1 d . . .
O2 O 0.22311(15) 0.10916(10) 0.45054(8) 0.0160(3) Uani 1 d . . .
O7 O 0.11985(18) 0.10328(11) 0.12327(10) 0.0263(3) Uani 1 d . . .
N3 N 0.10069(17) 0.25074(11) 0.30379(9) 0.0122(3) Uani 1 d . . .
O14 O 0.1873(2) 0.58203(13) 0.21830(13) 0.0420(5) Uani 1 d . . .
N7 N 0.2546(2) 0.11699(12) 0.10640(10) 0.0192(3) Uani 1 d . . .
O8 O 0.2938(2) 0.06540(11) 0.05438(10) 0.0310(4) Uani 1 d . . .
O13 O 0.3831(2) 0.77320(12) 0.47154(11) 0.0324(4) Uani 1 d . . .
N5 N 0.18073(17) 0.37443(10) 0.10169(9) 0.0114(3) Uani 1 d . . .
N2 N 0.29952(18) 0.15425(11) 0.32604(9) 0.0129(3) Uani 1 d . . .
O15 O 0.2378(2) 0.88683(14) 0.24545(11) 0.0386(4) Uani 1 d . . .
N9 N 0.1355(2) 0.55197(13) 0.34927(13) 0.0270(4) Uani 1 d . . .
N6 N 0.5198(2) 0.38690(12) 0.33615(11) 0.0201(3) Uani 1 d . . .
N1 N 0.40848(18) 0.10219(11) 0.34487(9) 0.0128(3) Uani 1 d . . .
C16 C 0.3250(2) 0.40301(12) -0.01354(11) 0.0126(3) Uani 1 d . . .
O10 O 0.4036(2) 0.38471(14) 0.37228(13) 0.0408(5) Uani 1 d . . .
C12 C -0.1215(2) 0.30737(13) 0.32298(11) 0.0143(3) Uani 1 d . . .
H12 H -0.1927 0.3413 0.3050 0.017 Uiso 1 calc . . R
N10 N 0.5471(2) 0.72051(14) 0.39584(12) 0.0285(4) Uani 1 d . . .
C21 C 0.2405(2) 0.46066(12) -0.05549(11) 0.0125(3) Uani 1 d . . .
O11 O 0.64903(19) 0.43871(12) 0.36470(12) 0.0344(4) Uani 1 d . . .
N11 N 0.0143(2) 0.84194(13) 0.15284(12) 0.0247(4) Uani 1 d . . .
C17 C 0.4490(2) 0.37905(13) -0.04830(12) 0.0148(3) Uani 1 d . . .
H17 H 0.5043 0.3415 -0.0203 0.018 Uiso 1 calc . . R
C19 C 0.4078(2) 0.46624(14) -0.16283(12) 0.0177(4) Uani 1 d . . .
H19 H 0.4348 0.4877 -0.2128 0.021 Uiso 1 calc . . R
C13 C -0.0005(2) 0.30049(12) 0.27894(11) 0.0123(3) Uani 1 d . . .
C25 C 0.1549(3) 0.89480(15) 0.18162(14) 0.0242(4) Uani 1 d . . .
H25 H 0.1953 0.9431 0.1504 0.029 Uiso 1 calc . . R
C11 C -0.1324(2) 0.26152(13) 0.39523(11) 0.0151(3) Uani 1 d . . .
H11 H -0.2112 0.2655 0.4267 0.018 Uiso 1 calc . . R
C10 C -0.0258(2) 0.20985(13) 0.42053(11) 0.0140(3) Uani 1 d . . .
H10 H -0.0320 0.1792 0.4686 0.017 Uiso 1 calc . . R
C31 C 0.4846(3) 0.73089(19) 0.46316(17) 0.0374(6) Uani 1 d . . .
H31 H 0.5202 0.7037 0.5093 0.045 Uiso 1 calc . . R
C8 C 0.2106(2) 0.15201(12) 0.38562(11) 0.0130(3) Uani 1 d . . .
C20 C 0.2857(2) 0.49151(13) -0.13043(12) 0.0165(4) Uani 1 d . . .
H20 H 0.2326 0.5297 -0.1589 0.020 Uiso 1 calc . . R
C14 C 0.0326(2) 0.34434(12) 0.20156(11) 0.0126(3) Uani 1 d . . .
C26 C -0.0554(4) 0.7627(2) 0.19623(19) 0.0496(8) Uani 1 d . . .
H26A H -0.0568 0.7049 0.1645 0.074 Uiso 1 calc . . GR
H26B H -0.1601 0.7645 0.2026 0.074 Uiso 1 calc . . GR
H26C H 0.0049 0.7665 0.2502 0.074 Uiso 1 calc . . GR
C18 C 0.4912(2) 0.40930(13) -0.12235(12) 0.0169(4) Uani 1 d . . .
H18 H 0.5728 0.3923 -0.1446 0.020 Uiso 1 calc . . R
C33 C 0.4988(4) 0.7646(2) 0.32068(17) 0.0415(6) Uani 1 d . . .
H33A H 0.4195 0.7959 0.3317 0.062 Uiso 1 calc . . GR
H33B H 0.4584 0.7167 0.2746 0.062 Uiso 1 calc . . GR
H33C H 0.5872 0.8094 0.3072 0.062 Uiso 1 calc . . GR
C9 C 0.0898(2) 0.20557(12) 0.37174(11) 0.0125(3) Uani 1 d . . .
C15 C 0.2964(2) 0.36607(12) 0.06451(11) 0.0132(3) Uani 1 d . . .
H15 H 0.3657 0.3344 0.0894 0.016 Uiso 1 calc . . R
C30 C -0.0026(3) 0.5879(2) 0.34216(19) 0.0426(6) Uani 1 d . . .
H30A H 0.0189 0.6468 0.3763 0.064 Uiso 1 calc . . GR
H30B H -0.0864 0.5435 0.3604 0.064 Uiso 1 calc . . GR
H30C H -0.0319 0.5971 0.2851 0.064 Uiso 1 calc . . GR
C27 C -0.0687(3) 0.8563(2) 0.07465(17) 0.0398(6) Uani 1 d . . .
H27A H -0.0096 0.9107 0.0533 0.060 Uiso 1 calc . . GR
H27B H -0.1685 0.8658 0.0833 0.060 Uiso 1 calc . . GR
H27C H -0.0831 0.8020 0.0353 0.060 Uiso 1 calc . . GR
C28 C 0.2174(3) 0.55377(16) 0.28548(17) 0.0336(5) Uani 1 d . . .
H28 H 0.3064 0.5311 0.2934 0.040 Uiso 1 calc . . R
C29 C 0.1841(3) 0.52169(18) 0.42825(16) 0.0359(5) Uani 1 d . . .
H29A H 0.2027 0.5730 0.4712 0.054 Uiso 1 calc . . GR
H29B H 0.2783 0.5016 0.4259 0.054 Uiso 1 calc . . GR
H29C H 0.1038 0.4703 0.4404 0.054 Uiso 1 calc . . GR
C32 C 0.6751(4) 0.6788(3) 0.3909(3) 0.0693(11) Uani 1 d . . .
H32A H 0.7680 0.7271 0.3891 0.104 Uiso 1 calc . . GR
H32B H 0.6536 0.6356 0.3413 0.104 Uiso 1 calc . . GR
H32C H 0.6896 0.6456 0.4389 0.104 Uiso 1 calc . . GR
N4 N 0.16104(18) 0.33152(11) 0.17451(9) 0.0125(3) Uani 1 d . . .
C7 C 0.5094(2) 0.10078(13) 0.29523(11) 0.0132(3) Uani 1 d . . .
H7 H 0.5028 0.1329 0.2482 0.016 Uiso 1 calc . . R
O1 O 0.57740(15) -0.00188(9) 0.44006(8) 0.0139(2) Uani 1 d . . .
C5 C 0.6660(2) 0.00691(12) 0.37895(11) 0.0126(3) Uani 1 d . . .
C6 C 0.6323(2) 0.05271(12) 0.30761(11) 0.0128(3) Uani 1 d . . .
C2 C 0.8551(2) 0.01902(14) 0.25022(12) 0.0175(4) Uani 1 d . . .
H2 H 0.9161 0.0218 0.2076 0.021 Uiso 1 calc . . R
C1 C 0.7286(2) 0.05761(13) 0.24478(11) 0.0157(3) Uani 1 d . . .
H1 H 0.7059 0.0879 0.1982 0.019 Uiso 1 calc . . R
C4 C 0.7980(2) -0.02992(14) 0.38427(12) 0.0178(4) Uani 1 d . . .
H4 H 0.8244 -0.0587 0.4312 0.021 Uiso 1 calc . . R
C3 C 0.8894(2) -0.02430(14) 0.32113(12) 0.0187(4) Uani 1 d . . .
H3 H 0.9753 -0.0500 0.3262 0.022 Uiso 1 calc . . R
O12 O 0.22148(19) -0.10151(11) 0.40992(11) 0.0244(3) Uani 1 d . . .
O5 O -0.1139(2) 0.30472(12) -0.01778(12) 0.0360(4) Uani 1 d . . .
N8 N -0.3352(2) 0.18846(13) -0.04297(11) 0.0240(4) Uani 1 d . . .
C22 C -0.2329(2) 0.26247(15) -0.06345(14) 0.0224(4) Uani 1 d . . .
H22 H -0.2536 0.2830 -0.1155 0.027 Uiso 1 calc . . R
C23 C -0.3095(3) 0.1541(2) 0.03829(15) 0.0368(6) Uani 1 d . . .
H23A H -0.2138 0.1921 0.0695 0.055 Uiso 1 calc . . GR
H23B H -0.3033 0.0899 0.0309 0.055 Uiso 1 calc . . GR
H23C H -0.3945 0.1579 0.0681 0.055 Uiso 1 calc . . GR
C24 C -0.4718(3) 0.1375(2) -0.09975(16) 0.0374(6) Uani 1 d . . .
H24A H -0.4763 0.1667 -0.1507 0.056 Uiso 1 calc . . GR
H24B H -0.5635 0.1383 -0.0748 0.056 Uiso 1 calc . . GR
H24C H -0.4664 0.0736 -0.1115 0.056 Uiso 1 calc . . GR
H12A H 0.214(4) -0.105(2) 0.360(2) 0.045(9) Uiso 1 d . . .
H12B H 0.269(4) -0.136(2) 0.429(2) 0.042(9) Uiso 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
Cu1 O6 2.0207(13) . ?
Cu1 O9 2.1880(14) . ?
Cu1 N3 1.9438(15) . ?
Cu1 N2 2.0499(15) . ?
Cu1 N4 2.0352(15) . ?
Cu2 Cu2 2.9871(4) 2_565 ?
Cu2 O4 1.9460(13) . ?
Cu2 O4 1.9665(12) 2_565 ?
Cu2 O3 1.9618(13) . ?
Cu2 N5 1.9369(15) . ?
Cu2 O5 2.2670(16) . ?
Cu3 Cu3 3.0153(4) 2_656 ?
Cu3 O2 1.9701(13) . ?
Cu3 N1 1.9350(15) . ?
Cu3 O1 1.9532(12) . ?
Cu3 O1 1.9830(12) 2_656 ?
Cu3 O12 2.2696(16) . ?
O4 Cu2 1.9665(12) 2_565 ?
O4 C21 1.344(2) . ?
O3 C14 1.267(2) . ?
O6 N7 1.292(2) . ?
O9 N6 1.271(2) . ?
O2 C8 1.273(2) . ?
O7 N7 1.240(2) . ?
N3 C13 1.334(2) . ?
N3 C9 1.330(2) . ?
O14 C28 1.217(3) . ?
N7 O8 1.234(2) . ?
O13 C31 1.231(3) . ?
N5 C15 1.286(2) . ?
N5 N4 1.3904(19) . ?
N2 N1 1.393(2) . ?
N2 C8 1.324(2) . ?
O15 C25 1.227(3) . ?
N9 C30 1.448(3) . ?
N9 C28 1.340(3) . ?
N9 C29 1.438(3) . ?
N6 O10 1.250(2) . ?
N6 O11 1.234(2) . ?
N1 C7 1.285(2) . ?
C16 C21 1.418(2) . ?
C16 C17 1.409(2) . ?
C16 C15 1.442(2) . ?
C12 C13 1.387(2) . ?
C12 C11 1.397(2) . ?
N10 C31 1.304(3) . ?
N10 C33 1.486(3) . ?
N10 C32 1.428(4) . ?
C21 C20 1.402(2) . ?
N11 C25 1.316(3) . ?
N11 C26 1.456(3) . ?
N11 C27 1.444(3) . ?
C17 C18 1.377(3) . ?
C19 C20 1.383(3) . ?
C19 C18 1.393(3) . ?
C13 C14 1.483(2) . ?
C11 C10 1.394(2) . ?
C10 C9 1.388(2) . ?
C8 C9 1.484(2) . ?
C14 N4 1.327(2) . ?
C7 C6 1.442(2) . ?
O1 Cu3 1.9830(12) 2_656 ?
O1 C5 1.339(2) . ?
C5 C6 1.417(2) . ?
C5 C4 1.406(2) . ?
C6 C1 1.410(2) . ?
C2 C1 1.377(3) . ?
C2 C3 1.391(3) . ?
C4 C3 1.384(3) . ?
O5 C22 1.220(3) . ?
N8 C22 1.334(3) . ?
N8 C23 1.457(3) . ?
N8 C24 1.444(3) . ?

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
O6 Cu1 O9 82.15(5) . . ?
O6 Cu1 N2 99.09(6) . . ?
O6 Cu1 N4 99.81(6) . . ?
N3 Cu1 O6 154.12(6) . . ?
N3 Cu1 O9 123.60(6) . . ?
N3 Cu1 N2 78.64(6) . . ?
N3 Cu1 N4 79.22(6) . . ?
N2 Cu1 O9 93.18(6) . . ?
N4 Cu1 O9 100.94(6) . . ?
N4 Cu1 N2 157.75(6) . . ?
O4 Cu2 Cu2 39.98(4) 2_565 2_565 ?
O4 Cu2 Cu2 40.48(4) . 2_565 ?
O4 Cu2 O4 80.46(6) . 2_565 ?
O4 Cu2 O3 172.29(6) . . ?
O4 Cu2 O5 94.17(6) 2_565 . ?
O4 Cu2 O5 91.09(7) . . ?
O3 Cu2 Cu2 144.58(4) . 2_565 ?
O3 Cu2 O4 104.91(5) . 2_565 ?
O3 Cu2 O5 93.99(7) . . ?
N5 Cu2 Cu2 133.02(4) . 2_565 ?
N5 Cu2 O4 92.67(6) . . ?
N5 Cu2 O4 172.00(6) . 2_565 ?
N5 Cu2 O3 81.55(6) . . ?
N5 Cu2 O5 90.02(6) . . ?
O5 Cu2 Cu2 93.45(5) . 2_565 ?
O2 Cu3 Cu3 143.28(4) . 2_656 ?
O2 Cu3 O1 104.47(5) . 2_656 ?
O2 Cu3 O12 94.43(6) . . ?
N1 Cu3 Cu3 131.50(5) . 2_656 ?
N1 Cu3 O2 81.25(6) . . ?
N1 Cu3 O1 92.29(6) . . ?
N1 Cu3 O1 165.52(6) . 2_656 ?
N1 Cu3 O12 106.36(7) . . ?
O1 Cu3 Cu3 40.36(4) . 2_656 ?
O1 Cu3 Cu3 39.64(4) 2_656 2_656 ?
O1 Cu3 O2 169.63(6) . . ?
O1 Cu3 O1 80.00(6) . 2_656 ?
O1 Cu3 O12 95.17(6) . . ?
O1 Cu3 O12 86.66(6) 2_656 . ?
O12 Cu3 Cu3 91.15(4) . 2_656 ?
Cu2 O4 Cu2 99.54(6) . 2_565 ?
C21 O4 Cu2 126.36(11) . . ?
C21 O4 Cu2 133.08(11) . 2_565 ?
C14 O3 Cu2 109.54(11) . . ?
N7 O6 Cu1 108.17(11) . . ?
N6 O9 Cu1 111.26(11) . . ?
C8 O2 Cu3 109.67(11) . . ?
C13 N3 Cu1 118.92(12) . . ?
C9 N3 Cu1 119.61(12) . . ?
C9 N3 C13 121.46(15) . . ?
O7 N7 O6 118.30(16) . . ?
O8 N7 O6 118.50(17) . . ?
O8 N7 O7 123.19(18) . . ?
C15 N5 Cu2 127.82(12) . . ?
C15 N5 N4 118.41(15) . . ?
N4 N5 Cu2 113.71(11) . . ?
N1 N2 Cu1 134.87(11) . . ?
C8 N2 Cu1 114.79(12) . . ?
C8 N2 N1 109.76(14) . . ?
C28 N9 C30 119.8(2) . . ?
C28 N9 C29 122.8(2) . . ?
C29 N9 C30 117.2(2) . . ?
O10 N6 O9 118.86(17) . . ?
O11 N6 O9 119.59(17) . . ?
O11 N6 O10 121.52(19) . . ?
N2 N1 Cu3 114.07(11) . . ?
C7 N1 Cu3 128.07(12) . . ?
C7 N1 N2 117.85(15) . . ?
C21 C16 C15 125.33(16) . . ?
C17 C16 C21 119.37(16) . . ?
C17 C16 C15 115.30(16) . . ?
C13 C12 C11 117.63(16) . . ?
C31 N10 C33 119.6(2) . . ?
C31 N10 C32 124.6(3) . . ?
C32 N10 C33 115.4(3) . . ?
O4 C21 C16 122.34(16) . . ?
O4 C21 C20 119.98(16) . . ?
C20 C21 C16 117.67(16) . . ?
C25 N11 C26 120.3(2) . . ?
C25 N11 C27 121.0(2) . . ?
C27 N11 C26 118.5(2) . . ?
C18 C17 C16 122.23(17) . . ?
C20 C19 C18 121.47(17) . . ?
N3 C13 C12 121.39(16) . . ?
N3 C13 C14 112.44(15) . . ?
C12 C13 C14 126.17(16) . . ?
O15 C25 N11 126.6(2) . . ?
C10 C11 C12 120.39(16) . . ?
C9 C10 C11 117.95(16) . . ?
O13 C31 N10 126.3(3) . . ?
O2 C8 N2 125.17(16) . . ?
O2 C8 C9 120.59(16) . . ?
N2 C8 C9 114.24(15) . . ?
C19 C20 C21 121.34(17) . . ?
O3 C14 C13 120.27(16) . . ?
O3 C14 N4 125.54(16) . . ?
N4 C14 C13 114.19(15) . . ?
C17 C18 C19 117.92(17) . . ?
N3 C9 C10 121.16(16) . . ?
N3 C9 C8 112.21(15) . . ?
C10 C9 C8 126.62(16) . . ?
N5 C15 C16 123.77(16) . . ?
O14 C28 N9 126.6(2) . . ?
N5 N4 Cu1 134.94(11) . . ?
C14 N4 Cu1 114.92(12) . . ?
C14 N4 N5 109.66(14) . . ?
N1 C7 C6 124.40(16) . . ?
Cu3 O1 Cu3 100.00(6) . 2_656 ?
C5 O1 Cu3 127.64(11) . . ?
C5 O1 Cu3 131.75(11) . 2_656 ?
O1 C5 C6 122.39(16) . . ?
O1 C5 C4 120.01(16) . . ?
C4 C5 C6 117.60(16) . . ?
C5 C6 C7 124.86(16) . . ?
C1 C6 C7 115.66(16) . . ?
C1 C6 C5 119.39(16) . . ?
C1 C2 C3 118.24(17) . . ?
C2 C1 C6 122.10(17) . . ?
C3 C4 C5 121.42(17) . . ?
C4 C3 C2 121.22(17) . . ?
C22 O5 Cu2 148.33(16) . . ?
C22 N8 C23 120.3(2) . . ?
C22 N8 C24 122.4(2) . . ?
C24 N8 C23 117.2(2) . . ?
O5 C22 N8 123.8(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vb37
_database_code_depnum_ccdc_archive 'CCDC 1404685'
_audit_update_record             
;
2015-06-03 deposited with the CCDC.
2016-03-24 downloaded from the CCDC.
;
_audit_creation_date             2015-04-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4959)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C27 H27 Cl2 Cu3 N7 O6'
_chemical_formula_sum            'C27 H27 Cl2 Cu3 N7 O6'
_chemical_formula_weight         807.08
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   10.2012(5)
_cell_length_b                   12.0131(6)
_cell_length_c                   14.1568(6)
_cell_angle_alpha                82.402(2)
_cell_angle_beta                 82.701(2)
_cell_angle_gamma                78.506(2)
_cell_volume                     1676.09(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    2.095
_exptl_absorpt_correction_T_max  0.533
_exptl_absorpt_correction_T_min  0.475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (sheldrick, 2003)'
_exptl_crystal_colour            'clear greenish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             814
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            63591
_diffrn_reflns_theta_full        28.38
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         2.39
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                7486
_reflns_number_total             8370
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         2.713
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.139
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         8370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0837P)²+5.0345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1487
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C20(H20), C15(H15), C5(H5), C10(H10), C3(H3), C2(H2), C11(H11),
 C4(H4), C17(H17), C12(H12), C19(H19), C18(H18), C22(H22), C25(H25)
2.b Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C26(H26A,H26B,H26C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cu1 Cu 1.00934(4) 0.50336(3) 0.24930(3) 0.01848(11) Uani 1 d . . .
Cu2 Cu 0.94591(4) 0.68306(3) -0.07239(3) 0.01940(11) Uani 1 d . . .
Cu3 Cu 0.95090(4) 0.32212(4) 0.57312(3) 0.02294(12) Uani 1 d . . .
Cl2 Cl 0.83483(8) 0.38340(7) 0.71920(5) 0.02246(17) Uani 1 d . . .
Cl1 Cl 0.82999(8) 0.65847(7) -0.19695(5) 0.02150(16) Uani 1 d . . .
O1 O 1.1043(2) 0.6926(2) -0.15665(17) 0.0259(5) Uani 1 d . . .
O2 O 0.7938(2) 0.6606(2) 0.02636(17) 0.0230(5) Uani 1 d . . .
O3 O 0.7978(2) 0.3941(2) 0.49896(17) 0.0243(5) Uani 1 d . . .
O4 O 1.1101(3) 0.2577(2) 0.63068(19) 0.0306(6) Uani 1 d . . .
N2 N 0.9680(3) 0.5836(2) 0.11831(19) 0.0185(5) Uani 1 d . . .
O6 O 0.8900(3) 0.8737(2) -0.0781(2) 0.0380(7) Uani 1 d . . .
O5 O 0.8837(3) 0.1586(2) 0.5884(2) 0.0379(7) Uani 1 d . . .
N3 N 0.8135(3) 0.5296(2) 0.26289(19) 0.0179(5) Uani 1 d . . .
C16 C 1.2745(3) 0.3016(3) 0.4998(2) 0.0225(6) Uani 1 d . . .
C7 C 1.1756(3) 0.5995(3) 0.0385(2) 0.0202(6) Uani 1 d . . .
H7 H 1.2112 0.5621 0.0940 0.024 Uiso 1 calc . . R
N4 N 0.9706(3) 0.4324(2) 0.38520(19) 0.0179(5) Uani 1 d . . .
C6 C 1.2663(3) 0.6350(3) -0.0409(2) 0.0218(6) Uani 1 d . . .
C9 C 0.7468(3) 0.5828(3) 0.1892(2) 0.0183(6) Uani 1 d . . .
N1 N 1.0473(3) 0.6170(2) 0.03615(18) 0.0182(5) Uani 1 d . . .
C21 C 1.2348(4) 0.2524(3) 0.5933(3) 0.0231(7) Uani 1 d . . .
N5 N 1.0518(3) 0.3739(2) 0.45382(19) 0.0177(5) Uani 1 d . . .
C14 C 0.8419(3) 0.4359(3) 0.4169(2) 0.0183(6) Uani 1 d . . .
C8 C 0.8383(3) 0.6127(3) 0.1041(2) 0.0173(6) Uani 1 d . . .
C20 C 1.3384(4) 0.1956(4) 0.6492(3) 0.0345(9) Uani 1 d . . .
H20 H 1.3155 0.1617 0.7105 0.041 Uiso 1 calc . . R
C15 C 1.1809(3) 0.3620(3) 0.4344(2) 0.0204(6) Uani 1 d . . .
H15 H 1.2148 0.3942 0.3752 0.024 Uiso 1 calc . . R
N7 N 0.9519(5) 1.0458(3) -0.1223(3) 0.0445(9) Uani 1 d . . .
N6 N 0.9339(5) -0.0343(3) 0.6248(3) 0.0456(10) Uani 1 d . . .
C5 C 1.4012(4) 0.6238(4) -0.0232(3) 0.0337(8) Uani 1 d . . .
H5 H 1.4263 0.5928 0.0370 0.040 Uiso 1 calc . . R
C10 C 0.6075(4) 0.6033(3) 0.1968(3) 0.0266(7) Uani 1 d . . .
H10 H 0.5613 0.6401 0.1455 0.032 Uiso 1 calc . . R
C13 C 0.7479(3) 0.4946(3) 0.3462(2) 0.0193(6) Uani 1 d . . .
C3 C 1.4580(4) 0.7032(4) -0.1829(3) 0.0372(9) Uani 1 d . . .
H3 H 1.5215 0.7270 -0.2303 0.045 Uiso 1 calc . . R
C2 C 1.3280(4) 0.7137(3) -0.2026(3) 0.0303(8) Uani 1 d . . .
H2 H 1.3055 0.7434 -0.2637 0.036 Uiso 1 calc . . R
C11 C 0.5384(4) 0.5673(4) 0.2832(3) 0.0298(8) Uani 1 d . . .
H11 H 0.4448 0.5805 0.2902 0.036 Uiso 1 calc . . R
C1 C 1.2266(3) 0.6806(3) -0.1325(2) 0.0214(6) Uani 1 d . . .
C4 C 1.4970(4) 0.6573(5) -0.0924(3) 0.0427(11) Uani 1 d . . .
H4 H 1.5857 0.6497 -0.0794 0.051 Uiso 1 calc . . R
C17 C 1.4122(4) 0.2936(4) 0.4674(3) 0.0327(8) Uani 1 d . . .
H17 H 1.4368 0.3265 0.4061 0.039 Uiso 1 calc . . R
C12 C 0.6089(4) 0.5117(3) 0.3591(3) 0.0261(7) Uani 1 d . . .
H12 H 0.5639 0.4867 0.4169 0.031 Uiso 1 calc . . R
C19 C 1.4725(4) 0.1888(4) 0.6159(3) 0.0424(10) Uani 1 d . . .
H19 H 1.5380 0.1509 0.6549 0.051 Uiso 1 calc . . R
C18 C 1.5116(4) 0.2384(4) 0.5237(3) 0.0416(10) Uani 1 d . . .
H18 H 1.6020 0.2342 0.5013 0.050 Uiso 1 calc . . R
C22 C 0.9603(5) 0.0697(3) 0.6139(3) 0.0359(9) Uani 1 d . . .
H22 H 1.0453 0.0768 0.6267 0.043 Uiso 1 calc . . R
C25 C 0.9736(5) 0.9344(4) -0.1086(3) 0.0356(9) Uani 1 d . . .
H25 H 1.0614 0.8970 -0.1235 0.043 Uiso 1 calc . . R
C27 C 0.8189(9) 1.1105(6) -0.1052(8) 0.101(3) Uani 1 d . . .
H27A H 0.7568 1.0773 -0.1330 0.151 Uiso 1 calc . . GR
H27B H 0.8167 1.1879 -0.1336 0.151 Uiso 1 calc . . GR
H27C H 0.7940 1.1097 -0.0374 0.151 Uiso 1 calc . . GR
C26 C 1.0590(7) 1.1103(5) -0.1542(4) 0.0560(14) Uani 1 d . . .
H26A H 1.0681 1.1551 -0.1048 0.084 Uiso 1 calc . . GR
H26B H 1.0374 1.1600 -0.2112 0.084 Uiso 1 calc . . GR
H26C H 1.1420 1.0584 -0.1675 0.084 Uiso 1 calc . . GR
C23 C 0.8048(8) -0.0541(6) 0.6082(8) 0.094(3) Uani 1 d . . .
H23A H 0.7480 0.0176 0.5903 0.141 Uiso 1 calc . . GR
H23B H 0.7643 -0.0910 0.6656 0.141 Uiso 1 calc . . GR
H23C H 0.8159 -0.1020 0.5575 0.141 Uiso 1 calc . . GR
C24 C 1.0343(7) -0.1341(4) 0.6503(4) 0.0616(16) Uani 1 d . . .
H24A H 1.0590 -0.1785 0.5971 0.092 Uiso 1 calc . . GR
H24B H 0.9980 -0.1796 0.7045 0.092 Uiso 1 calc . . GR
H24C H 1.1123 -0.1102 0.6663 0.092 Uiso 1 calc . . GR


_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 Cl2 2.4040(9) 2_766 ?
Cu1 Cl1 2.4120(9) 2_765 ?
Cu1 N2 2.027(3) . ?
Cu1 N3 1.948(3) . ?
Cu1 N4 2.023(3) . ?
Cu2 Cl1 2.3242(9) . ?
Cu2 O1 1.896(2) . ?
Cu2 O2 1.987(2) . ?
Cu2 O6 2.240(3) . ?
Cu2 N1 1.953(3) . ?
Cu3 Cl2 2.3777(9) . ?
Cu3 O3 1.982(2) . ?
Cu3 O4 1.890(3) . ?
Cu3 O5 2.183(3) . ?
Cu3 N5 1.958(3) . ?
Cl2 Cu1 2.4040(9) 2_766 ?
Cl1 Cu1 2.4120(9) 2_765 ?
O1 C1 1.311(4) . ?
O2 C8 1.266(4) . ?
O3 C14 1.267(4) . ?
O4 C21 1.307(4) . ?
N2 N1 1.391(4) . ?
N2 C8 1.333(4) . ?
O6 C25 1.231(5) . ?
O5 C22 1.232(5) . ?
N3 C9 1.338(4) . ?
N3 C13 1.341(4) . ?
C16 C21 1.420(5) . ?
C16 C15 1.438(5) . ?
C16 C17 1.410(5) . ?
C7 C6 1.437(4) . ?
C7 N1 1.288(4) . ?
N4 N5 1.384(4) . ?
N4 C14 1.327(4) . ?
C6 C5 1.407(5) . ?
C6 C1 1.415(5) . ?
C9 C8 1.479(4) . ?
C9 C10 1.385(5) . ?
C21 C20 1.411(5) . ?
N5 C15 1.294(4) . ?
C14 C13 1.485(4) . ?
C20 C19 1.380(6) . ?
N7 C25 1.304(6) . ?
N7 C27 1.431(9) . ?
N7 C26 1.456(7) . ?
N6 C22 1.315(5) . ?
N6 C23 1.437(8) . ?
N6 C24 1.452(7) . ?
C5 C4 1.373(6) . ?
C10 C11 1.394(5) . ?
C13 C12 1.383(5) . ?
C3 C2 1.367(6) . ?
C3 C4 1.400(6) . ?
C2 C1 1.419(5) . ?
C11 C12 1.390(5) . ?
C17 C18 1.378(6) . ?
C19 C18 1.405(6) . ?

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
Cl2 Cu1 Cl1 98.39(3) 2_766 2_765 ?
N2 Cu1 Cl2 97.90(8) . 2_766 ?
N2 Cu1 Cl1 97.96(8) . 2_765 ?
N3 Cu1 Cl2 131.85(8) . 2_766 ?
N3 Cu1 Cl1 129.76(8) . 2_765 ?
N3 Cu1 N2 78.51(11) . . ?
N3 Cu1 N4 78.79(11) . . ?
N4 Cu1 Cl2 97.62(8) . 2_766 ?
N4 Cu1 Cl1 96.07(8) . 2_765 ?
N4 Cu1 N2 157.29(11) . . ?
O1 Cu2 Cl1 91.64(8) . . ?
O1 Cu2 O2 173.22(10) . . ?
O1 Cu2 O6 91.74(12) . . ?
O1 Cu2 N1 92.75(11) . . ?
O2 Cu2 Cl1 93.11(7) . . ?
O2 Cu2 O6 92.35(11) . . ?
O6 Cu2 Cl1 98.35(9) . . ?
N1 Cu2 Cl1 149.47(9) . . ?
N1 Cu2 O2 80.71(10) . . ?
N1 Cu2 O6 111.69(12) . . ?
O3 Cu3 Cl2 92.89(8) . . ?
O3 Cu3 O5 90.23(11) . . ?
O4 Cu3 Cl2 92.75(9) . . ?
O4 Cu3 O3 173.25(11) . . ?
O4 Cu3 O5 92.87(12) . . ?
O4 Cu3 N5 92.25(11) . . ?
O5 Cu3 Cl2 96.11(9) . . ?
N5 Cu3 Cl2 143.00(8) . . ?
N5 Cu3 O3 81.01(10) . . ?
N5 Cu3 O5 120.21(12) . . ?
Cu3 Cl2 Cu1 97.23(3) . 2_766 ?
Cu2 Cl1 Cu1 95.43(3) . 2_765 ?
C1 O1 Cu2 126.6(2) . . ?
C8 O2 Cu2 110.0(2) . . ?
C14 O3 Cu3 109.6(2) . . ?
C21 O4 Cu3 128.5(2) . . ?
N1 N2 Cu1 133.7(2) . . ?
C8 N2 Cu1 116.3(2) . . ?
C8 N2 N1 110.0(3) . . ?
C25 O6 Cu2 120.7(3) . . ?
C22 O5 Cu3 120.0(3) . . ?
C9 N3 Cu1 119.5(2) . . ?
C9 N3 C13 121.1(3) . . ?
C13 N3 Cu1 119.3(2) . . ?
C21 C16 C15 123.5(3) . . ?
C17 C16 C21 119.9(3) . . ?
C17 C16 C15 116.6(3) . . ?
N1 C7 C6 122.9(3) . . ?
N5 N4 Cu1 133.3(2) . . ?
C14 N4 Cu1 116.2(2) . . ?
C14 N4 N5 110.4(3) . . ?
C5 C6 C7 116.3(3) . . ?
C5 C6 C1 119.9(3) . . ?
C1 C6 C7 123.8(3) . . ?
N3 C9 C8 112.3(3) . . ?
N3 C9 C10 121.0(3) . . ?
C10 C9 C8 126.8(3) . . ?
N2 N1 Cu2 114.0(2) . . ?
C7 N1 Cu2 127.6(2) . . ?
C7 N1 N2 118.3(3) . . ?
O4 C21 C16 124.5(3) . . ?
O4 C21 C20 118.5(3) . . ?
C20 C21 C16 117.0(3) . . ?
N4 N5 Cu3 113.5(2) . . ?
C15 N5 Cu3 127.9(2) . . ?
C15 N5 N4 118.6(3) . . ?
O3 C14 N4 125.5(3) . . ?
O3 C14 C13 120.8(3) . . ?
N4 C14 C13 113.8(3) . . ?
O2 C8 N2 125.1(3) . . ?
O2 C8 C9 121.5(3) . . ?
N2 C8 C9 113.4(3) . . ?
C19 C20 C21 122.0(4) . . ?
N5 C15 C16 123.3(3) . . ?
C25 N7 C27 120.5(5) . . ?
C25 N7 C26 122.7(5) . . ?
C27 N7 C26 116.8(5) . . ?
C22 N6 C23 121.0(5) . . ?
C22 N6 C24 122.0(5) . . ?
C23 N6 C24 117.0(5) . . ?
C4 C5 C6 121.9(4) . . ?
C9 C10 C11 118.3(3) . . ?
N3 C13 C14 111.9(3) . . ?
N3 C13 C12 121.3(3) . . ?
C12 C13 C14 126.8(3) . . ?
C2 C3 C4 121.1(4) . . ?
C3 C2 C1 121.9(4) . . ?
C12 C11 C10 120.1(3) . . ?
O1 C1 C6 124.7(3) . . ?
O1 C1 C2 118.5(3) . . ?
C6 C1 C2 116.8(3) . . ?
C5 C4 C3 118.4(4) . . ?
C18 C17 C16 122.0(4) . . ?
C13 C12 C11 118.2(3) . . ?
C20 C19 C18 120.9(4) . . ?
C17 C18 C19 118.2(4) . . ?
O5 C22 N6 126.5(5) . . ?
O6 C25 N7 126.8(5) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.500 0.000 -0.404 261.4 43.2 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vb34c
_database_code_depnum_ccdc_archive 'CCDC 1404686'
_audit_update_record             
;
2015-06-03 deposited with the CCDC.
2016-03-24 downloaded from the CCDC.
;
_audit_creation_date             2015-04-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H21 Cu3 N10 O15, N O3'
_chemical_formula_sum            'C19 H21 Cu3 N11 O18'
_chemical_formula_weight         882.09
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.3863(4)
_cell_length_b                   13.2194(7)
_cell_length_c                   30.5186(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.022(2)
_cell_angle_gamma                90.00
_cell_volume                     2975.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    2.228
_exptl_absorpt_correction_T_max  0.513
_exptl_absorpt_correction_T_min  0.357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (sheldrick, 2003)'
_exptl_crystal_colour            'clear greenish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.969
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1772
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1229
_diffrn_reflns_av_unetI/netI     0.0680
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            87331
_diffrn_reflns_theta_full        28.46
_diffrn_reflns_theta_max         28.46
_diffrn_reflns_theta_min         2.53
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                5174
_reflns_number_total             7477
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.039
_refine_diff_density_min         -0.829
_refine_diff_density_rms         0.138
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     484
_refine_ls_number_reflns         7477
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0682
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0280P)²+16.0431P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1332
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 O16-Cu2
 2.313 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O14) = Uanis(O18) = Uanis(O19) = Uanis(O13)
4. Others
 Sof(O13)=Sof(O14)=1-FVAR(1)
 Sof(O19)=Sof(O18)=FVAR(1)
5.a Rotating group:
 O12(H12B), O11(H11A,H11B), O10(H10B)
5.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C2(H2), C3(H3), C9(H9), C17(H17), C4(H4), C18(H18), C5(H5),
 C19(H19), C6(H6), C16(H16), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
H12A H 1.105(8) 0.093(5) 0.319(2) 0.03(2) Uiso 1 d . . .
H10A H 0.138(9) 0.249(5) 0.584(2) 0.05(2) Uiso 1 d . . .
C12 C 0.6984(6) 0.0675(4) 0.53319(16) 0.0186(10) Uani 1 d . . .
C13 C 0.6303(7) 0.1288(4) 0.56931(16) 0.0203(10) Uani 1 d . . .
C15 C 0.5050(6) 0.3993(4) 0.64821(16) 0.0194(10) Uani 1 d . . .
C1 C 0.9696(7) 0.4383(4) 0.36195(17) 0.0224(11) Uani 1 d . . .
C11 C 0.7035(6) -0.0367(4) 0.53258(17) 0.0220(11) Uani 1 d . . .
H11 H 0.6668 -0.0747 0.5562 0.026 Uiso 1 calc . . R
C7 C 0.8674(7) 0.1494(4) 0.43029(17) 0.0229(11) Uani 1 d . . .
C8 C 0.8118(7) 0.0783(4) 0.46414(16) 0.0217(11) Uani 1 d . . .
C2 C 0.9815(7) 0.5401(4) 0.35254(18) 0.0274(12) Uani 1 d . . .
H2 H 0.9448 0.5883 0.3724 0.033 Uiso 1 calc . . R
C14 C 0.5751(7) 0.3703(4) 0.60638(17) 0.0214(11) Uani 1 d . . .
C3 C 1.0498(7) 0.5693(4) 0.31255(18) 0.0307(13) Uani 1 d . . .
H3 H 1.0600 0.6374 0.3054 0.037 Uiso 1 calc . . R
C9 C 0.8182(7) -0.0253(4) 0.46045(18) 0.0254(11) Uani 1 d . . .
H9 H 0.8569 -0.0556 0.4351 0.030 Uiso 1 calc . . R
C17 C 0.4281(8) 0.5169(4) 0.70365(18) 0.0316(13) Uani 1 d . . .
H17 H 0.4187 0.5828 0.7140 0.038 Uiso 1 calc . . R
C4 C 1.1016(7) 0.4959(4) 0.28402(18) 0.0301(12) Uani 1 d . . .
H4 H 1.1448 0.5139 0.2570 0.036 Uiso 1 calc . . R
C18 C 0.3787(7) 0.4368(4) 0.72904(18) 0.0311(13) Uani 1 d . . .
H18 H 0.3366 0.4480 0.7568 0.037 Uiso 1 calc . . R
C5 C 1.0893(7) 0.3951(4) 0.29550(17) 0.0275(12) Uani 1 d . . .
H5 H 1.1268 0.3459 0.2761 0.033 Uiso 1 calc . . R
C19 C 0.3920(7) 0.3398(4) 0.71302(17) 0.0271(12) Uani 1 d . . .
H19 H 0.3574 0.2859 0.7303 0.033 Uiso 1 calc . . R
C6 C 0.8932(7) 0.3982(4) 0.40167(16) 0.0219(11) Uani 1 d . . .
H6 H 0.8474 0.4397 0.4231 0.026 Uiso 1 calc . . R
C16 C 0.4920(7) 0.4989(4) 0.66257(17) 0.0256(11) Uani 1 d . . .
H16 H 0.5256 0.5522 0.6449 0.031 Uiso 1 calc . . R
C10 C 0.7660(7) -0.0830(4) 0.49508(17) 0.0243(11) Uani 1 d . . .
H10 H 0.7723 -0.1532 0.4935 0.029 Uiso 1 calc . . R
N4 N 0.7525(5) 0.1243(3) 0.50005(13) 0.0192(9) Uani 1 d . . .
N3 N 0.8358(6) 0.2473(3) 0.43882(13) 0.0215(9) Uani 1 d . . .
N6 N 0.5795(5) 0.2759(3) 0.59963(13) 0.0194(8) Uani 1 d . . .
N5 N 0.6436(5) 0.2288(3) 0.56332(13) 0.0192(8) Uani 1 d . . .
N2 N 0.8944(5) 0.3024(3) 0.40463(13) 0.0203(9) Uani 1 d A . .
N7 N 0.4526(6) 0.3208(3) 0.67375(13) 0.0227(9) Uani 1 d . . .
N10 N 0.5841(7) 0.1805(4) 0.3126(2) 0.0446(14) Uani 1 d . . .
N9 N 0.3965(6) 0.3106(4) 0.43343(16) 0.0312(11) Uani 1 d . . .
N1 N 1.0255(5) 0.3664(3) 0.33350(14) 0.0231(9) Uani 1 d A . .
N8 N 1.1242(6) 0.3718(3) 0.52404(14) 0.0227(9) Uani 1 d . . .
O19 O 0.7307(16) 0.2267(11) 0.3080(5) 0.0603(15) Uani 0.444(7) d A 1 .
O13 O 0.7530(13) 0.1688(9) 0.3134(4) 0.0603(15) Uani 0.556(7) d A 2 .
O18 O 0.5288(14) 0.2593(10) 0.3235(4) 0.0603(15) Uani 0.444(7) d A 1 .
O14 O 0.4560(11) 0.2339(8) 0.2906(3) 0.0603(15) Uani 0.556(7) d A 2 .
O9 O 0.6755(6) 0.4128(3) 0.50408(14) 0.0262(9) Uani 1 d . . .
O12 O 1.1299(5) 0.1474(3) 0.31679(13) 0.0264(8) Uani 1 d A . .
H12B H 1.2431 0.1520 0.3233 0.040 Uiso 1 d . . GR
O2 O 0.5647(5) 0.0851(3) 0.60171(11) 0.0256(8) Uani 1 d . . .
O1 O 0.9409(5) 0.1152(3) 0.39705(12) 0.0280(8) Uani 1 d A . .
O6 O 0.4367(5) 0.2596(3) 0.46694(13) 0.0354(9) Uani 1 d . . .
O5 O 1.2452(5) 0.3992(3) 0.55066(13) 0.0345(9) Uani 1 d . . .
O11 O 0.3567(5) 0.0928(3) 0.68233(12) 0.0295(9) Uani 1 d . . .
H11A H 0.4057 0.0347 0.6807 0.044 Uiso 1 d . . GR
H11B H 0.2441 0.0883 0.6748 0.044 Uiso 1 d . . GR
O4 O 1.1013(5) 0.4144(3) 0.48784(12) 0.0314(9) Uani 1 d . . .
O8 O 0.4523(6) 0.4013(3) 0.43176(14) 0.0414(10) Uani 1 d . . .
O3 O 1.0227(5) 0.2994(3) 0.53390(13) 0.0344(9) Uani 1 d . . .
O10 O 0.1899(5) 0.2067(3) 0.60902(13) 0.0328(9) Uani 1 d . . .
H10B H 0.1111 0.2069 0.6285 0.049 Uiso 1 d . . GR
O7 O 0.3042(7) 0.2754(4) 0.40277(18) 0.0682(16) Uani 1 d . . .
O20 O 0.5072(9) 0.1034(4) 0.3198(2) 0.0820(19) Uani 1 d A . .
Cu1 Cu 0.73627(8) 0.27037(5) 0.502163(19) 0.01924(15) Uani 1 d . . .
Cu3 Cu 0.99922(9) 0.22721(5) 0.35772(2) 0.02402(16) Uani 1 d . . .
Cu2 Cu 0.47281(8) 0.18766(5) 0.64251(2) 0.02284(16) Uani 1 d . . D
N11 N 0.8740(6) 0.1191(4) 0.67871(15) 0.0287(10) Uani 1 d . . .
O17 O 0.9037(6) 0.2011(3) 0.66123(18) 0.0550(14) Uani 1 d . . .
O16 O 0.7260(5) 0.1038(4) 0.69448(14) 0.0447(11) Uani 1 d . . D
O15 O 0.9925(5) 0.0507(3) 0.67910(16) 0.0420(11) Uani 1 d . . .
H14 H 0.608(6) 0.416(4) 0.5865(16) 0.013(13) Uiso 1 d . . .
H9A H 0.736(7) 0.459(4) 0.5044(17) 0.014(15) Uiso 1 d . . .
H9B H 0.611(8) 0.417(4) 0.4840(19) 0.021(17) Uiso 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
C12 C13 1.478(7) . ?
C12 C11 1.379(7) . ?
C12 N4 1.338(6) . ?
C13 N5 1.338(6) . ?
C13 O2 1.264(6) . ?
C15 C14 1.454(7) . ?
C15 C16 1.392(7) . ?
C15 N7 1.366(6) . ?
C1 C2 1.380(7) . ?
C1 C6 1.463(7) . ?
C1 N1 1.365(6) . ?
C11 C10 1.398(7) . ?
C7 C8 1.470(7) . ?
C7 N3 1.343(6) . ?
C7 O1 1.260(6) . ?
C8 C9 1.375(7) . ?
C8 N4 1.347(6) . ?
C2 C3 1.400(8) . ?
C14 N6 1.266(6) . ?
C3 C4 1.371(8) . ?
C9 C10 1.375(7) . ?
C17 C18 1.372(8) . ?
C17 C16 1.383(7) . ?
C4 C5 1.382(8) . ?
C18 C19 1.378(8) . ?
C5 N1 1.330(6) . ?
C19 N7 1.325(6) . ?
C6 N2 1.270(6) . ?
N4 Cu1 1.936(4) . ?
N3 N2 1.362(5) . ?
N3 Cu1 2.126(4) . ?
N6 N5 1.376(5) . ?
N6 Cu2 1.950(4) . ?
N5 Cu1 2.095(4) . ?
N2 Cu3 1.937(4) . ?
N7 Cu2 2.011(4) . ?
N10 O19 1.257(14) . ?
N10 O13 1.256(11) . ?
N10 O18 1.173(13) . ?
N10 O14 1.333(11) . ?
N10 O20 1.194(7) . ?
N9 O6 1.248(6) . ?
N9 O8 1.269(6) . ?
N9 O7 1.220(6) . ?
N1 Cu3 1.997(4) . ?
N8 O5 1.230(5) . ?
N8 O4 1.243(5) . ?
N8 O3 1.262(5) . ?
O19 O18 1.646(16) . ?
O19 Cu3 2.433(13) . ?
O13 Cu3 2.339(10) . ?
O9 Cu1 1.937(4) . ?
O12 Cu3 1.932(4) . ?
O2 Cu2 1.984(3) . ?
O1 Cu3 1.968(4) . ?
O6 Cu1 2.413(4) . ?
O11 Cu2 1.973(3) . ?
O3 Cu1 2.312(4) . ?
O10 Cu2 2.291(4) . ?
N11 O17 1.233(6) . ?
N11 O16 1.234(5) . ?
N11 O15 1.257(6) . ?

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
C11 C12 C13 124.7(4) . . ?
N4 C12 C13 112.5(4) . . ?
N4 C12 C11 122.8(4) . . ?
N5 C13 C12 114.2(4) . . ?
O2 C13 C12 119.5(4) . . ?
O2 C13 N5 126.3(5) . . ?
C16 C15 C14 124.0(5) . . ?
N7 C15 C14 115.2(4) . . ?
N7 C15 C16 120.8(5) . . ?
C2 C1 C6 123.9(5) . . ?
N1 C1 C2 121.4(5) . . ?
N1 C1 C6 114.7(4) . . ?
C12 C11 C10 117.3(5) . . ?
N3 C7 C8 114.9(4) . . ?
O1 C7 C8 119.0(5) . . ?
O1 C7 N3 126.1(4) . . ?
C9 C8 C7 124.5(5) . . ?
N4 C8 C7 113.5(4) . . ?
N4 C8 C9 122.0(5) . . ?
C1 C2 C3 118.7(5) . . ?
N6 C14 C15 114.6(5) . . ?
C4 C3 C2 118.9(5) . . ?
C10 C9 C8 118.5(5) . . ?
C18 C17 C16 119.5(5) . . ?
C3 C4 C5 119.8(5) . . ?
C17 C18 C19 119.4(5) . . ?
N1 C5 C4 121.8(5) . . ?
N7 C19 C18 122.1(5) . . ?
N2 C6 C1 114.7(4) . . ?
C17 C16 C15 118.7(5) . . ?
C9 C10 C11 120.3(5) . . ?
C12 N4 C8 119.0(4) . . ?
C12 N4 Cu1 120.9(3) . . ?
C8 N4 Cu1 120.1(3) . . ?
C7 N3 N2 107.5(4) . . ?
C7 N3 Cu1 112.7(3) . . ?
N2 N3 Cu1 139.4(3) . . ?
C14 N6 N5 126.1(4) . . ?
C14 N6 Cu2 117.8(3) . . ?
N5 N6 Cu2 116.0(3) . . ?
C13 N5 N6 107.8(4) . . ?
C13 N5 Cu1 114.2(3) . . ?
N6 N5 Cu1 137.8(3) . . ?
C6 N2 N3 125.9(4) . . ?
C6 N2 Cu3 117.4(3) . . ?
N3 N2 Cu3 116.6(3) . . ?
C15 N7 Cu2 111.4(3) . . ?
C19 N7 C15 119.4(4) . . ?
C19 N7 Cu2 129.2(4) . . ?
O19 N10 O14 106.2(9) . . ?
O13 N10 O19 37.1(7) . . ?
O13 N10 O14 138.9(9) . . ?
O18 N10 O19 85.2(9) . . ?
O18 N10 O13 117.7(9) . . ?
O18 N10 O14 54.9(7) . . ?
O18 N10 O20 122.0(7) . . ?
O20 N10 O19 148.9(9) . . ?
O20 N10 O13 111.9(8) . . ?
O20 N10 O14 102.3(6) . . ?
O6 N9 O8 118.7(5) . . ?
O7 N9 O6 121.4(5) . . ?
O7 N9 O8 119.9(5) . . ?
C1 N1 Cu3 111.6(3) . . ?
C5 N1 C1 119.3(4) . . ?
C5 N1 Cu3 129.1(4) . . ?
O5 N8 O4 120.9(4) . . ?
O5 N8 O3 119.1(4) . . ?
O4 N8 O3 120.0(4) . . ?
N10 O19 O18 45.3(6) . . ?
N10 O19 Cu3 127.5(10) . . ?
O18 O19 Cu3 122.7(8) . . ?
N10 O13 Cu3 135.4(7) . . ?
N10 O18 O19 49.6(7) . . ?
C13 O2 Cu2 109.7(3) . . ?
C7 O1 Cu3 109.8(3) . . ?
N9 O6 Cu1 120.4(3) . . ?
N8 O3 Cu1 124.6(3) . . ?
N4 Cu1 N3 78.55(16) . . ?
N4 Cu1 N5 77.98(16) . . ?
N4 Cu1 O9 170.15(19) . . ?
N4 Cu1 O6 89.03(15) . . ?
N4 Cu1 O3 97.03(15) . . ?
N3 Cu1 O6 86.52(15) . . ?
N3 Cu1 O3 92.99(16) . . ?
N5 Cu1 N3 156.52(16) . . ?
N5 Cu1 O6 92.65(15) . . ?
N5 Cu1 O3 90.29(15) . . ?
O9 Cu1 N3 105.00(16) . . ?
O9 Cu1 N5 98.10(16) . . ?
O9 Cu1 O6 82.09(17) . . ?
O9 Cu1 O3 91.99(18) . . ?
O3 Cu1 O6 173.71(13) . . ?
N2 Cu3 N1 81.44(17) . . ?
N2 Cu3 O19 96.8(3) . . ?
N2 Cu3 O13 105.5(3) . . ?
N2 Cu3 O1 80.00(16) . . ?
N1 Cu3 O19 82.2(4) . . ?
N1 Cu3 O13 100.3(3) . . ?
O13 Cu3 O19 19.1(3) . . ?
O12 Cu3 N2 172.15(18) . . ?
O12 Cu3 N1 101.69(18) . . ?
O12 Cu3 O19 90.8(3) . . ?
O12 Cu3 O13 81.1(3) . . ?
O12 Cu3 O1 96.67(17) . . ?
O1 Cu3 N1 161.44(16) . . ?
O1 Cu3 O19 100.4(4) . . ?
O1 Cu3 O13 85.1(3) . . ?
N6 Cu2 N7 80.65(17) . . ?
N6 Cu2 O2 79.84(15) . . ?
N6 Cu2 O11 175.87(17) . . ?
N6 Cu2 O10 91.51(16) . . ?
N7 Cu2 O10 91.52(16) . . ?
O2 Cu2 N7 158.71(16) . . ?
O2 Cu2 O10 97.42(15) . . ?
O11 Cu2 N7 102.62(17) . . ?
O11 Cu2 O2 97.28(15) . . ?
O11 Cu2 O10 85.90(15) . . ?
O17 N11 O16 119.6(5) . . ?
O17 N11 O15 119.8(4) . . ?
O16 N11 O15 120.6(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
