# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_sk-4_12_12
_database_code_depnum_ccdc_archive 'CCDC 1010924'
_audit_update_record             
;
2014-06-28 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H42 Cu2 N10 O18'
_chemical_formula_weight         933.82

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   c2/c

loop_
_symmetry_equiv_pos_as_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                   15.3483(9)
_cell_length_b                   12.7358(8)
_cell_length_c                   19.0760(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.446(4)
_cell_angle_gamma                90.00
_cell_volume                     3725.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    90
_cell_measurement_theta_min      3
_cell_measurement_theta_max      30

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1928
_exptl_absorpt_coefficient_mu    1.234
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7682
_exptl_absorpt_correction_T_max  0.9129
_exptl_absorpt_process_details   SADABAS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26925
_diffrn_reflns_av_R_equivalents  0.0811
_diffrn_reflns_av_sigmaI/netI    0.0674
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         27.09
_reflns_number_total             4116
_reflns_number_gt                2247
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SMART APEX II'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1245P)²+13.0985P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4079
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1406
_refine_ls_R_factor_gt           0.0756
_refine_ls_wR_factor_ref         0.2470
_refine_ls_wR_factor_gt          0.1962
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.055
_refine_ls_shift/su_mean         0.003

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.7425(3) 0.0698(4) 0.3335(2) 0.0607(12) Uani 1 1 d . . .
Cu2 Cu 0.85017(5) -0.01494(7) 0.34924(4) 0.0535(3) Uani 1 1 d . . .
O5 O 0.6335(4) 0.1281(6) 0.3895(3) 0.0989(19) Uani 1 1 d . . .
O4 O 0.7102(4) -0.0005(5) 0.4325(3) 0.0808(16) Uani 1 1 d . . .
O6 O 0.9304(4) 0.0258(5) 0.2443(3) 0.0887(19) Uani 1 1 d . . .
O7 O 1.0000 0.1729(5) 0.2500 0.0613(17) Uani 1 2 d S . .
O1 O 0.9550(3) 0.2950(4) 0.4223(2) 0.0692(13) Uani 1 1 d . . .
N4 N 0.6937(4) 0.0657(5) 0.3870(3) 0.0634(15) Uani 1 1 d . . .
O8 O 1.5000 -0.1082(9) 0.2500 0.141(4) Uani 1 2 d S . .
N2 N 0.8050(3) -0.1395(5) 0.2890(2) 0.0559(14) Uani 1 1 d . . .
N5 N 1.0000 0.0750(7) 0.2500 0.0548(19) Uani 1 2 d S . .
C8 C 1.0188(4) -0.0753(5) 0.4055(3) 0.0506(15) Uani 1 1 d . . .
H8 H 1.0610 -0.1267 0.4142 0.061 Uiso 1 1 calc R . .
C1 C 1.0409(4) 0.0299(6) 0.4250(3) 0.0500(15) Uani 1 1 d . . .
N6 N 1.5000 -0.0136(12) 0.2500 0.156(9) Uani 1 2 d S . .
C14 C 0.7319(5) -0.1947(7) 0.3231(4) 0.071(2) Uani 1 1 d . . .
H14A H 0.7548 -0.2260 0.3665 0.085 Uiso 1 1 calc R . .
H14B H 0.6890 -0.1427 0.3354 0.085 Uiso 1 1 calc R . .
C7 C 0.9769(7) 0.3984(6) 0.4464(5) 0.096(3) Uani 1 1 d . . .
H7A H 0.9296 0.4453 0.4347 0.145 Uiso 1 1 calc R . .
H7B H 1.0285 0.4219 0.4243 0.145 Uiso 1 1 calc R . .
H7C H 0.9875 0.3973 0.4964 0.145 Uiso 1 1 calc R . .
C12 C 0.7257(5) -0.1770(7) 0.1758(4) 0.081(2) Uani 1 1 d . . .
H12A H 0.7672 -0.2303 0.1630 0.097 Uiso 1 1 calc R . .
H12B H 0.7026 -0.1444 0.1330 0.097 Uiso 1 1 calc R . .
C2 C 1.1269(4) 0.0477(6) 0.4530(3) 0.0564(17) Uani 1 1 d . . .
H2 H 1.1651 -0.0084 0.4599 0.068 Uiso 1 1 calc R . .
C6 C 0.9839(4) 0.1145(5) 0.4156(3) 0.0498(15) Uani 1 1 d . . .
O9 O 1.5612(8) 0.0338(7) 0.2238(7) 0.190(5) Uani 1 1 d . . .
C10 C 0.8822(4) -0.2095(6) 0.2830(3) 0.0617(18) Uani 1 1 d . . .
H10A H 0.9199 -0.1824 0.2477 0.074 Uiso 1 1 calc R . .
H10B H 0.8633 -0.2794 0.2690 0.074 Uiso 1 1 calc R . .
C4 C 1.0984(5) 0.2312(6) 0.4604(3) 0.0611(19) Uani 1 1 d . . .
H4 H 1.1179 0.2983 0.4721 0.073 Uiso 1 1 calc R . .
C5 C 1.0142(4) 0.2173(5) 0.4338(3) 0.0543(16) Uani 1 1 d . . .
N3 N 0.6524(4) -0.2280(6) 0.2131(3) 0.0773(19) Uani 1 1 d . . .
H3BN H 0.6283 -0.2792 0.1862 0.093 Uiso 1 1 calc R . .
H3AN H 0.6110 -0.1802 0.2215 0.093 Uiso 1 1 calc R . .
C11 C 0.7696(5) -0.0990(7) 0.2188(4) 0.077(2) Uani 1 1 d . . .
H11A H 0.7293 -0.0421 0.2270 0.092 Uiso 1 1 calc R . .
H11B H 0.8176 -0.0704 0.1933 0.092 Uiso 1 1 calc R . .
C9 C 0.9320(4) -0.2142(5) 0.3542(3) 0.0590(17) Uani 1 1 d . . .
H9A H 0.8986 -0.2522 0.3880 0.071 Uiso 1 1 calc R . .
H9B H 0.9876 -0.2492 0.3498 0.071 Uiso 1 1 calc R . .
C13 C 0.6889(5) -0.2743(7) 0.2826(4) 0.080(2) Uani 1 1 d . . .
H13A H 0.6417 -0.3037 0.3087 0.096 Uiso 1 1 calc R . .
H13B H 0.7296 -0.3303 0.2732 0.096 Uiso 1 1 calc R . .
C3 C 1.1536(4) 0.1473(6) 0.4697(3) 0.0627(19) Uani 1 1 d . . .
H3A H 1.2101 0.1584 0.4877 0.075 Uiso 1 1 calc R . .
N1 N 0.9454(3) -0.1049(4) 0.3768(2) 0.0530(13) Uani 1 1 d . . .
O2 O 0.9019(3) 0.1069(4) 0.3900(2) 0.0563(11) Uani 1 1 d . . .
O10 O 0.8134(17) 0.1984(19) 0.5092(16) 0.455(18) 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
O3 N4 1.292(7) . ?
O3 Cu2 1.986(5) . ?
Cu2 O2 1.894(4) . ?
Cu2 N1 1.913(6) . ?
Cu2 N2 2.062(5) . ?
O5 N4 1.221(8) . ?
O4 N4 1.230(8) . ?
O6 N5 1.239(7) . ?
O7 N5 1.247(10) . ?
O1 C5 1.354(8) . ?
O1 C7 1.430(9) . ?
O8 N6 1.205(16) . ?
N2 C10 1.491(9) . ?
N2 C14 1.496(7) . ?
N2 C11 1.514(9) . ?
N5 O6 1.239(7) 2_755 ?
C8 N1 1.289(7) . ?
C8 C1 1.428(9) . ?
C8 H8 0.9300 . ?
C1 C6 1.394(9) . ?
C1 C2 1.420(8) . ?
N6 O9 1.240(11) . ?
N6 O9 1.240(11) 2_855 ?
C14 C13 1.420(10) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C12 C11 1.438(10) . ?
C12 N3 1.503(9) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C2 C3 1.367(10) . ?
C2 H2 0.9300 . ?
C6 O2 1.334(7) . ?
C6 C5 1.428(9) . ?
C10 C9 1.531(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C4 C3 1.370(10) . ?
C4 C5 1.379(9) . ?
C4 H4 0.9300 . ?
N3 C13 1.535(9) . ?
N3 H3BN 0.9000 . ?
N3 H3AN 0.9000 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C9 N1 1.468(9) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C3 H3A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 O3 Cu2 111.4(4) . . ?
O2 Cu2 N1 94.4(2) . . ?
O2 Cu2 O3 87.04(19) . . ?
N1 Cu2 O3 171.17(19) . . ?
O2 Cu2 N2 169.78(18) . . ?
N1 Cu2 N2 85.8(2) . . ?
O3 Cu2 N2 94.4(2) . . ?
C5 O1 C7 118.2(6) . . ?
O5 N4 O4 123.5(6) . . ?
O5 N4 O3 118.1(6) . . ?
O4 N4 O3 118.4(6) . . ?
C10 N2 C14 111.4(6) . . ?
C10 N2 C11 113.1(5) . . ?
C14 N2 C11 107.3(5) . . ?
C10 N2 Cu2 104.7(3) . . ?
C14 N2 Cu2 111.1(4) . . ?
C11 N2 Cu2 109.3(5) . . ?
O6 N5 O6 119.3(10) 2_755 . ?
O6 N5 O7 120.4(5) 2_755 . ?
O6 N5 O7 120.4(5) . . ?
N1 C8 C1 125.4(6) . . ?
N1 C8 H8 117.3 . . ?
C1 C8 H8 117.3 . . ?
C6 C1 C2 119.5(6) . . ?
C6 C1 C8 123.4(5) . . ?
C2 C1 C8 117.0(6) . . ?
O8 N6 O9 119.1(9) . . ?
O8 N6 O9 119.1(9) . 2_855 ?
O9 N6 O9 121.7(18) . 2_855 ?
C13 C14 N2 116.1(6) . . ?
C13 C14 H14A 108.3 . . ?
N2 C14 H14A 108.3 . . ?
C13 C14 H14B 108.3 . . ?
N2 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C11 C12 N3 111.7(6) . . ?
C11 C12 H12A 109.3 . . ?
N3 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
N3 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C3 C2 C1 120.0(7) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
O2 C6 C1 124.6(6) . . ?
O2 C6 C5 116.6(6) . . ?
C1 C6 C5 118.8(6) . . ?
N2 C10 C9 108.9(5) . . ?
N2 C10 H10A 109.9 . . ?
C9 C10 H10A 109.9 . . ?
N2 C10 H10B 109.9 . . ?
C9 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C3 C4 C5 120.9(7) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
O1 C5 C4 125.3(6) . . ?
O1 C5 C6 114.9(6) . . ?
C4 C5 C6 119.8(7) . . ?
C12 N3 C13 108.8(6) . . ?
C12 N3 H3BN 109.9 . . ?
C13 N3 H3BN 109.9 . . ?
C12 N3 H3AN 109.9 . . ?
C13 N3 H3AN 109.9 . . ?
H3BN N3 H3AN 108.3 . . ?
C12 C11 N2 114.3(7) . . ?
C12 C11 H11A 108.7 . . ?
N2 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
N2 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
N1 C9 C10 106.3(6) . . ?
N1 C9 H9A 110.5 . . ?
C10 C9 H9A 110.5 . . ?
N1 C9 H9B 110.5 . . ?
C10 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
C14 C13 N3 109.8(7) . . ?
C14 C13 H13A 109.7 . . ?
N3 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
N3 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C2 C3 C4 121.0(6) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C8 N1 C9 120.7(6) . . ?
C8 N1 Cu2 125.8(5) . . ?
C9 N1 Cu2 113.1(4) . . ?
C6 O2 Cu2 125.6(4) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.09
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.113
_refine_diff_density_min         -0.884
_refine_diff_density_rms         0.110
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_f
_audit_block_doi                 10.5517/cc12xyhf
_database_code_depnum_ccdc_archive 'CCDC 1010925'
_audit_update_record             
;
2015-05-16 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H47 Cu2 N10 O16.50'
_chemical_formula_weight         950.86

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           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                   15.2074(4)
_cell_length_b                   12.6983(3)
_cell_length_c                   20.2333(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.6930(10)
_cell_angle_gamma                90
_cell_volume                     3905.51(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    120
_cell_measurement_theta_min      2
_cell_measurement_theta_max      27.2

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_F_000             1972
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.176
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8715
_exptl_absorpt_correction_T_max  0.9544
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30906
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.014
_diffrn_reflns_theta_max         27.203
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4348
_reflns_number_gt                3525
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0883P)²+7.9546P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4348
_refine_ls_number_parameters     302
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1570
_refine_ls_wR_factor_gt          0.1461
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.85057(2) 0.97385(3) 0.35027(2) 0.04044(16) Uani 1 1 d . . . . .
N2 N 0.6609(2) 0.7482(3) 0.22326(18) 0.0656(9) Uani 1 1 d . . . . .
H2 H 0.6075 0.7459 0.2081 0.079 Uiso 1 1 calc R U . . .
N3 N 0.94876(18) 0.8892(2) 0.37928(14) 0.0433(6) Uani 1 1 d . . . . .
C7 C 1.0195(2) 0.9230(3) 0.40733(17) 0.0445(7) Uani 1 1 d . . . . .
H7 H 1.0627 0.8735 0.4181 0.053 Uiso 1 1 calc R U . . .
O1 O 0.89894(14) 1.10188(18) 0.38485(12) 0.0438(5) Uani 1 1 d . . . . .
O2 O 0.94646(17) 1.29545(18) 0.41406(13) 0.0529(6) Uani 1 1 d . . . . .
C11 C 1.0891(3) 1.2351(3) 0.45671(18) 0.0540(9) Uani 1 1 d . . . . .
H11 H 1.1067 1.3034 0.4672 0.065 Uiso 1 1 calc R U . . .
O3 O 0.74033(15) 1.0530(2) 0.33175(13) 0.0499(6) Uani 1 1 d . . . . .
O5 O 0.6267(2) 1.1047(3) 0.38433(18) 0.0809(10) Uani 1 1 d . . . . .
O4 O 0.7110(2) 0.9826(2) 0.42580(15) 0.0669(8) Uani 1 1 d . . . . .
O6 O 0.9296(3) 1.0118(3) 0.24666(17) 0.0885(12) Uani 1 1 d . . . . .
O7 O 1.0000 1.1571(3) 0.2500 0.0674(11) Uani 1 2 d S T P . .
N1 N 0.80829(19) 0.8444(2) 0.29676(15) 0.0494(7) Uani 1 1 d . . . . .
C14 C 1.0383(2) 1.0313(3) 0.42379(16) 0.0415(7) Uani 1 1 d . . . . .
C15 C 0.9784(2) 1.1138(2) 0.41126(15) 0.0373(6) Uani 1 1 d . . . . .
N4 N 0.6905(2) 1.0473(2) 0.38276(17) 0.0511(7) Uani 1 1 d . . . . .
N5 N 1.0000 1.0607(4) 0.2500 0.0572(11) Uani 1 2 d S T P . .
C1 C 0.7746(3) 0.8817(3) 0.2297(2) 0.0584(9) Uani 1 1 d . . . . .
H1A H 0.7305 0.9358 0.2357 0.070 Uiso 1 1 calc R U . . .
H1B H 0.8229 0.9132 0.2063 0.070 Uiso 1 1 calc R U . . .
C2 C 0.7359(3) 0.7963(4) 0.1887(2) 0.0618(10) Uani 1 1 d . . . . .
H2A H 0.7801 0.7432 0.1807 0.074 Uiso 1 1 calc R U . . .
H2B H 0.7155 0.8244 0.1464 0.074 Uiso 1 1 calc R U . . .
C3 C 0.6925(3) 0.7041(3) 0.2889(2) 0.0663(11) Uani 1 1 d . . . . .
H3A H 0.6434 0.6743 0.3120 0.080 Uiso 1 1 calc R U . . .
H3B H 0.7352 0.6487 0.2819 0.080 Uiso 1 1 calc R U . . .
C4 C 0.7335(3) 0.7902(3) 0.32907(19) 0.0549(9) Uani 1 1 d . . . . .
H4A H 0.7546 0.7611 0.3709 0.066 Uiso 1 1 calc R U . . .
H4B H 0.6888 0.8421 0.3385 0.066 Uiso 1 1 calc R U . . .
C5 C 0.8883(3) 0.7778(3) 0.2940(2) 0.0590(10) Uani 1 1 d . . . . .
H5A H 0.9262 0.8042 0.2600 0.071 Uiso 1 1 calc R U . . .
H5B H 0.8717 0.7062 0.2825 0.071 Uiso 1 1 calc R U . . .
C6 C 0.9381(3) 0.7784(3) 0.3607(2) 0.0567(9) Uani 1 1 d . . . . .
H6A H 0.9050 0.7410 0.3936 0.068 Uiso 1 1 calc R U . . .
H6B H 0.9951 0.7448 0.3571 0.068 Uiso 1 1 calc R U . . .
C10 C 1.0064(2) 1.2180(3) 0.42841(16) 0.0435(7) Uani 1 1 d . . . . .
C9 C 0.9680(3) 1.3998(3) 0.4366(3) 0.0728(12) Uani 1 1 d . . . . .
H9A H 1.0213 1.4237 0.4162 0.087 Uiso 1 1 calc R U . . .
H9B H 0.9783 1.3994 0.4842 0.087 Uiso 1 1 calc R U . . .
C8 C 0.8942(4) 1.4725(3) 0.4192(3) 0.0874(17) Uani 1 1 d . . . . .
H8A H 0.9086 1.5422 0.4342 0.131 Uiso 1 1 calc R U . . .
H8B H 0.8418 1.4489 0.4399 0.131 Uiso 1 1 calc R U . . .
H8C H 0.8847 1.4732 0.3720 0.131 Uiso 1 1 calc R U . . .
C12 C 1.1456(2) 1.1526(3) 0.46950(19) 0.0570(9) Uani 1 1 d . . . . .
H12 H 1.2006 1.1655 0.4892 0.068 Uiso 1 1 calc R U . . .
C13 C 1.1219(2) 1.0519(3) 0.45357(19) 0.0517(8) Uani 1 1 d . . . . .
H13 H 1.1607 0.9967 0.4623 0.062 Uiso 1 1 calc R U . . .
N6 N 1.5000 0.9667(5) 0.2500 0.0733(15) Uani 1 2 d S T P . .
O12 O 1.5626(10) 0.9108(14) 0.2643(8) 0.094(6) Uani 0.25 1 d . . P . .
O8 O 1.4309(6) 1.0120(6) 0.2605(5) 0.087(2) Uani 0.5 1 d . . P . .
O9 O 1.5000 0.8707(8) 0.2500 0.095(4) Uani 0.5 2 d S T P . .
O11 O 1.5000 1.0547(12) 0.2500 0.25(2) Uani 0.5 2 d S T P . .
C102 C 0.7500 0.7500 0.0000 0.051(3) Uani 0.5 2 d DS . P . .
O100 O 0.7053(7) 0.6937(8) -0.0061(5) 0.108(3) Uani 0.5 1 d . . P . .
C101 C 0.752(3) 0.755(3) 0.0587(5) 0.186(19) Uani 0.25 1 d D . P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.909(2) . ?
Cu1 N3 1.918(3) . ?
Cu1 O3 1.981(2) . ?
Cu1 N1 2.061(3) . ?
N2 C2 1.486(5) . ?
N2 C3 1.506(6) . ?
N2 H2 0.8600 . ?
N3 C7 1.276(4) . ?
N3 C6 1.464(4) . ?
C7 C14 1.441(5) . ?
C7 H7 0.9300 . ?
O1 C15 1.315(4) . ?
O2 C10 1.366(4) . ?
O2 C9 1.437(5) . ?
C11 C12 1.375(6) . ?
C11 C10 1.384(5) . ?
C11 H11 0.9300 . ?
O3 N4 1.300(4) . ?
O5 N4 1.214(4) . ?
O4 N4 1.231(4) . ?
O6 N5 1.238(4) . ?
O7 N5 1.225(6) . ?
N1 C5 1.484(5) . ?
N1 C4 1.496(4) . ?
N1 C1 1.513(5) . ?
C14 C15 1.407(5) . ?
C14 C13 1.414(5) . ?
C15 C10 1.430(4) . ?
N5 O6 1.238(4) 2_755 ?
C1 C2 1.477(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.489(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.530(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C9 C8 1.487(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C12 C13 1.365(6) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
N6 O11 1.117(15) . ?
N6 O12 1.215(11) . ?
N6 O12 1.216(11) 2_855 ?
N6 O9 1.220(11) . ?
N6 O8 1.222(9) . ?
N6 O8 1.222(9) 2_855 ?
O12 O9 1.110(18) . ?
O12 O8 1.38(2) 2_855 ?
O8 O11 1.207(9) . ?
O8 O12 1.38(2) 2_855 ?
O9 O12 1.110(18) 2_855 ?
O11 O8 1.207(9) 2_855 ?
C102 O100 0.992(11) . ?
C102 O100 0.992(11) 7_665 ?
C102 C101 1.189(10) . ?
C102 C101 1.189(10) 7_665 ?
O100 C101 1.42(3) 7_665 ?
O100 C101 1.66(3) . ?
C101 O100 1.42(3) 7_665 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N3 94.42(10) . . ?
O1 Cu1 O3 87.23(10) . . ?
N3 Cu1 O3 171.59(11) . . ?
O1 Cu1 N1 169.39(11) . . ?
N3 Cu1 N1 86.66(12) . . ?
O3 Cu1 N1 93.24(12) . . ?
C2 N2 C3 109.8(3) . . ?
C2 N2 H2 125.1 . . ?
C3 N2 H2 125.1 . . ?
C7 N3 C6 121.5(3) . . ?
C7 N3 Cu1 125.9(2) . . ?
C6 N3 Cu1 112.4(2) . . ?
N3 C7 C14 125.6(3) . . ?
N3 C7 H7 117.2 . . ?
C14 C7 H7 117.2 . . ?
C15 O1 Cu1 125.9(2) . . ?
C10 O2 C9 116.9(3) . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
N4 O3 Cu1 109.4(2) . . ?
C5 N1 C4 112.9(3) . . ?
C5 N1 C1 113.6(3) . . ?
C4 N1 C1 107.2(3) . . ?
C5 N1 Cu1 103.4(2) . . ?
C4 N1 Cu1 111.5(2) . . ?
C1 N1 Cu1 108.3(2) . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 C7 123.1(3) . . ?
C13 C14 C7 116.4(3) . . ?
O1 C15 C14 124.7(3) . . ?
O1 C15 C10 117.9(3) . . ?
C14 C15 C10 117.3(3) . . ?
O5 N4 O4 124.6(4) . . ?
O5 N4 O3 118.2(3) . . ?
O4 N4 O3 117.2(3) . . ?
O7 N5 O6 120.1(3) . . ?
O7 N5 O6 120.1(3) . 2_755 ?
O6 N5 O6 119.8(6) . 2_755 ?
C2 C1 N1 113.1(3) . . ?
C2 C1 H1A 109.0 . . ?
N1 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
N1 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
C1 C2 N2 109.7(3) . . ?
C1 C2 H2A 109.7 . . ?
N2 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
N2 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C4 C3 N2 109.0(4) . . ?
C4 C3 H3A 109.9 . . ?
N2 C3 H3A 109.9 . . ?
C4 C3 H3B 109.9 . . ?
N2 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
C3 C4 N1 114.2(3) . . ?
C3 C4 H4A 108.7 . . ?
N1 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
N1 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
N1 C5 C6 110.4(3) . . ?
N1 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
N1 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
N3 C6 C5 106.2(3) . . ?
N3 C6 H6A 110.5 . . ?
C5 C6 H6A 110.5 . . ?
N3 C6 H6B 110.5 . . ?
C5 C6 H6B 110.5 . . ?
H6A C6 H6B 108.7 . . ?
O2 C10 C11 124.6(3) . . ?
O2 C10 C15 115.0(3) . . ?
C11 C10 C15 120.4(3) . . ?
O2 C9 C8 109.5(4) . . ?
O2 C9 H9A 109.8 . . ?
C8 C9 H9A 109.8 . . ?
O2 C9 H9B 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.1(4) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
O11 N6 O12 125.7(10) . . ?
O11 N6 O12 125.7(10) . 2_855 ?
O12 N6 O12 108.5(19) . 2_855 ?
O11 N6 O9 180.0 . . ?
O12 N6 O9 54.3(10) . . ?
O12 N6 O9 54.3(10) 2_855 . ?
O11 N6 O8 61.9(5) . . ?
O12 N6 O8 154.8(10) . . ?
O12 N6 O8 69.2(11) 2_855 . ?
O9 N6 O8 118.1(5) . . ?
O11 N6 O8 61.9(5) . 2_855 ?
O12 N6 O8 69.2(11) . 2_855 ?
O12 N6 O8 154.8(10) 2_855 2_855 ?
O9 N6 O8 118.1(5) . 2_855 ?
O8 N6 O8 123.9(9) . 2_855 ?
O9 O12 N6 63.1(8) . . ?
O9 O12 O8 113.7(11) . 2_855 ?
N6 O12 O8 55.6(8) . 2_855 ?
O11 O8 N6 54.8(9) . . ?
O11 O8 O12 106.3(11) . 2_855 ?
N6 O8 O12 55.2(7) . 2_855 ?
O12 O9 O12 125.4(18) . 2_855 ?
O12 O9 N6 62.7(9) . . ?
O12 O9 N6 62.7(9) 2_855 . ?
N6 O11 O8 63.3(8) . 2_855 ?
N6 O11 O8 63.3(8) . . ?
O8 O11 O8 126.6(15) 2_855 . ?
O100 C102 O100 180.0 . 7_665 ?
O100 C102 C101 99(2) . . ?
O100 C102 C101 81(2) 7_665 . ?
O100 C102 C101 81(2) . 7_665 ?
O100 C102 C101 99(2) 7_665 7_665 ?
C101 C102 C101 180.0 . 7_665 ?
C102 O100 C101 55.5(14) . 7_665 ?
C102 O100 C101 44.9(13) . . ?
C101 O100 C101 100.5(8) 7_665 . ?
C102 C101 O100 43.4(10) . 7_665 ?
C102 C101 O100 36.1(10) . . ?
O100 C101 O100 79.5(8) 7_665 . ?

_refine_diff_density_max         0.833
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.083

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_f1
_database_code_depnum_ccdc_archive 'CCDC 1010926'
_audit_update_record             
;
2014-06-28 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H25 Cu N5 O8'
_chemical_formula_weight         478.95

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                   23.3712(6)
_cell_length_b                   6.5538(2)
_cell_length_c                   12.8896(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.7490(10)
_cell_angle_gamma                90
_cell_volume                     1974.13(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    296
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      51.03

_exptl_crystal_description       Block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_F_000             996
_exptl_transmission_factor_min   0.6001
_exptl_transmission_factor_max   0.7458
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.163
_shelx_estimated_absorpt_T_min   0.653
_shelx_estimated_absorpt_T_max   0.801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24756
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.615
_diffrn_reflns_theta_max         29.171
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5305
_reflns_number_gt                4114
_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 Smart'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Platon (Spek, 2008)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.0403P)²+0.6694P] 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         5305
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0877
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.24283(2) 0.67208(3) 0.34142(2) 0.01981(8) Uani 1 1 d . . . . .
O1 O 0.28837(5) 0.9016(2) 0.31759(10) 0.0232(3) Uani 1 1 d . . . . .
C2 C 0.33308(7) 0.9578(3) 0.37348(14) 0.0188(4) Uani 1 1 d . . . . .
C3 C 0.35900(8) 1.1444(3) 0.34490(14) 0.0201(4) Uani 1 1 d . . . . .
H3 H 0.3434 1.2203 0.2884 0.024 Uiso 1 1 calc R U . . .
C4 C 0.40654(8) 1.2183(3) 0.39760(15) 0.0224(4) Uani 1 1 d . . . . .
C5 C 0.42977(8) 1.1086(3) 0.48100(16) 0.0270(4) Uani 1 1 d . . . . .
H5 H 0.4622 1.1591 0.5179 0.032 Uiso 1 1 calc R U . . .
C6 C 0.40530(8) 0.9280(3) 0.50888(15) 0.0259(4) Uani 1 1 d . . . . .
H6 H 0.4219 0.8543 0.5652 0.031 Uiso 1 1 calc R U . . .
C7 C 0.35650(8) 0.8448(3) 0.45825(14) 0.0198(4) Uani 1 1 d . . . . .
O8 O 0.43399(6) 1.3955(2) 0.37683(11) 0.0265(3) Uani 1 1 d . . . . .
C9 C 0.42011(8) 1.5046(3) 0.28373(15) 0.0257(4) Uani 1 1 d . . . . .
H9A H 0.3809 1.5611 0.2869 0.031 Uiso 1 1 calc R U . . .
H9B H 0.4225 1.4136 0.2226 0.031 Uiso 1 1 calc R U . . .
C10 C 0.46365(9) 1.6740(3) 0.27711(17) 0.0287(4) Uani 1 1 d . . . . .
H10A H 0.4612 1.7607 0.3388 0.034 Uiso 1 1 calc R U . . .
H10B H 0.4559 1.7561 0.2149 0.034 Uiso 1 1 calc R U . . .
H10C H 0.5021 1.6152 0.2733 0.034 Uiso 1 1 calc R U . . .
C11 C 0.33265(8) 0.6552(3) 0.49784(14) 0.0205(4) Uani 1 1 d . . . . .
C12 C 0.36346(8) 0.5466(3) 0.58541(15) 0.0277(4) Uani 1 1 d . . . . .
H12A H 0.3526 0.6076 0.6517 0.033 Uiso 1 1 calc R U . . .
H12B H 0.4049 0.5599 0.5765 0.033 Uiso 1 1 calc R U . . .
H12C H 0.3529 0.4019 0.5848 0.033 Uiso 1 1 calc R U . . .
N13 N 0.28469(6) 0.5814(2) 0.46202(12) 0.0212(3) Uani 1 1 d . . . . .
C14 C 0.25720(8) 0.4044(3) 0.51134(16) 0.0267(4) Uani 1 1 d . . . . .
H14A H 0.2672 0.4000 0.5862 0.032 Uiso 1 1 calc R U . . .
H14B H 0.2704 0.2762 0.4788 0.032 Uiso 1 1 calc R U . . .
C15 C 0.19340(8) 0.4272(3) 0.49668(15) 0.0252(4) Uani 1 1 d . . . . .
H15A H 0.1741 0.2993 0.5173 0.030 Uiso 1 1 calc R U . . .
H15B H 0.1793 0.5387 0.5414 0.030 Uiso 1 1 calc R U . . .
N16 N 0.17940(6) 0.4741(2) 0.38548(12) 0.0217(3) Uani 1 1 d . . . . .
C17 C 0.12325(8) 0.5791(3) 0.37559(17) 0.0284(4) Uani 1 1 d . . . . .
H17A H 0.1184 0.6294 0.3036 0.034 Uiso 1 1 calc R U . . .
H17B H 0.1231 0.6990 0.4223 0.034 Uiso 1 1 calc R U . . .
C18 C 0.07293(9) 0.4428(4) 0.40164(18) 0.0349(5) Uani 1 1 d . . . . .
H18A H 0.0755 0.4000 0.4752 0.042 Uiso 1 1 calc R U . . .
H18B H 0.0366 0.5182 0.3910 0.042 Uiso 1 1 calc R U . . .
N19 N 0.07411(8) 0.2596(3) 0.33259(18) 0.0389(5) Uani 1 1 d . . . . .
H19A H 0.0686(11) 0.306(4) 0.269(2) 0.044(8) Uiso 1 1 d . . . . .
H19B H 0.0443(13) 0.187(5) 0.347(2) 0.067(10) Uiso 1 1 d . . . . .
C20 C 0.12895(9) 0.1458(3) 0.34271(18) 0.0338(5) Uani 1 1 d . . . . .
H20A H 0.1290 0.0297 0.2936 0.041 Uiso 1 1 calc R U . . .
H20B H 0.1331 0.0907 0.4139 0.041 Uiso 1 1 calc R U . . .
C21 C 0.17846(9) 0.2865(3) 0.31991(16) 0.0272(4) Uani 1 1 d . . . . .
H21A H 0.2147 0.2110 0.3310 0.033 Uiso 1 1 calc R U . . .
H21B H 0.1764 0.3271 0.2460 0.033 Uiso 1 1 calc R U . . .
O22 O 0.20296(6) 0.7176(2) 0.20281(11) 0.0261(3) Uani 1 1 d . . . . .
O23 O 0.27011(6) 0.4974(2) 0.17289(12) 0.0360(4) Uani 1 1 d . . . . .
N24 N 0.22841(7) 0.5953(3) 0.13874(13) 0.0267(4) Uani 1 1 d . . . . .
O25 O 0.2118(7) 0.571(4) 0.0483(10) 0.028(2) Uani 0.71(12) 1 d . . P A 1
O25A O 0.205(2) 0.609(9) 0.053(2) 0.040(6) Uani 0.29(12) 1 d . . P A 2
N100 N 0.05462(8) -0.0049(3) 0.60167(15) 0.0381(5) Uani 1 1 d . . . . .
O101 O 0.02454(9) -0.0403(4) 0.67836(14) 0.0814(9) Uani 1 1 d . . . . .
O102 O 0.05204(9) -0.1124(4) 0.52491(17) 0.0683(6) Uani 1 1 d . . . . .
O103 O 0.08733(7) 0.1435(3) 0.60779(13) 0.0472(5) 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 O1 1.8706(13) . ?
Cu N13 1.9201(16) . ?
Cu O22 2.0264(14) . ?
Cu N16 2.0556(15) . ?
O1 C2 1.314(2) . ?
C2 C3 1.416(3) . ?
C2 C7 1.424(3) . ?
C3 C4 1.382(3) . ?
C3 H3 0.9500 . ?
C4 O8 1.355(2) . ?
C4 C5 1.397(3) . ?
C5 C6 1.365(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.416(3) . ?
C6 H6 0.9500 . ?
C7 C11 1.457(3) . ?
O8 C9 1.430(2) . ?
C9 C10 1.509(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 N13 1.300(2) . ?
C11 C12 1.509(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N13 C14 1.474(2) . ?
C14 C15 1.508(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 N16 1.498(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
N16 C17 1.486(2) . ?
N16 C21 1.492(2) . ?
C17 C18 1.518(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 N19 1.495(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N19 C20 1.487(3) . ?
N19 H19A 0.88(3) . ?
N19 H19B 0.87(3) . ?
C20 C21 1.511(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
O22 N24 1.301(2) . ?
O23 N24 1.243(2) . ?
N24 O25 1.234(13) . ?
N24 O25A 1.23(3) . ?
N100 O102 1.216(3) . ?
N100 O103 1.239(2) . ?
N100 O101 1.242(2) . ?

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 N13 95.56(6) . . ?
O1 Cu O22 89.59(6) . . ?
N13 Cu O22 169.41(6) . . ?
O1 Cu N16 165.22(6) . . ?
N13 Cu N16 86.72(6) . . ?
O22 Cu N16 90.66(6) . . ?
C2 O1 Cu 125.83(12) . . ?
O1 C2 C3 116.05(16) . . ?
O1 C2 C7 124.74(17) . . ?
C3 C2 C7 119.20(17) . . ?
C4 C3 C2 121.23(18) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
O8 C4 C3 125.63(18) . . ?
O8 C4 C5 114.38(17) . . ?
C3 C4 C5 119.98(18) . . ?
C6 C5 C4 119.27(18) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C7 123.41(18) . . ?
C5 C6 H6 118.3 . . ?
C7 C6 H6 118.3 . . ?
C6 C7 C2 116.90(17) . . ?
C6 C7 C11 118.48(17) . . ?
C2 C7 C11 124.59(16) . . ?
C4 O8 C9 119.41(15) . . ?
O8 C9 C10 105.62(16) . . ?
O8 C9 H9A 110.6 . . ?
C10 C9 H9A 110.6 . . ?
O8 C9 H9B 110.6 . . ?
C10 C9 H9B 110.6 . . ?
H9A C9 H9B 108.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N13 C11 C7 121.67(17) . . ?
N13 C11 C12 119.41(17) . . ?
C7 C11 C12 118.88(16) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 N13 C14 121.22(16) . . ?
C11 N13 Cu 126.89(13) . . ?
C14 N13 Cu 111.85(12) . . ?
N13 C14 C15 107.68(16) . . ?
N13 C14 H14A 110.2 . . ?
C15 C14 H14A 110.2 . . ?
N13 C14 H14B 110.2 . . ?
C15 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
N16 C15 C14 110.09(15) . . ?
N16 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
N16 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.2 . . ?
C17 N16 C21 109.06(16) . . ?
C17 N16 C15 111.03(15) . . ?
C21 N16 C15 111.98(15) . . ?
C17 N16 Cu 108.88(12) . . ?
C21 N16 Cu 111.65(11) . . ?
C15 N16 Cu 104.16(11) . . ?
N16 C17 C18 113.25(17) . . ?
N16 C17 H17A 108.9 . . ?
C18 C17 H17A 108.9 . . ?
N16 C17 H17B 108.9 . . ?
C18 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
N19 C18 C17 108.69(18) . . ?
N19 C18 H18A 110.0 . . ?
C17 C18 H18A 110.0 . . ?
N19 C18 H18B 110.0 . . ?
C17 C18 H18B 110.0 . . ?
H18A C18 H18B 108.3 . . ?
C20 N19 C18 111.92(18) . . ?
C20 N19 H19A 111.8(17) . . ?
C18 N19 H19A 105.6(18) . . ?
C20 N19 H19B 114(2) . . ?
C18 N19 H19B 107(2) . . ?
H19A N19 H19B 106(3) . . ?
N19 C20 C21 109.76(18) . . ?
N19 C20 H20A 109.7 . . ?
C21 C20 H20A 109.7 . . ?
N19 C20 H20B 109.7 . . ?
C21 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
N16 C21 C20 113.47(16) . . ?
N16 C21 H21A 108.9 . . ?
C20 C21 H21A 108.9 . . ?
N16 C21 H21B 108.9 . . ?
C20 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
N24 O22 Cu 105.08(11) . . ?
O25 N24 O23 120.2(12) . . ?
O25A N24 O23 134(3) . . ?
O25 N24 O22 122.6(12) . . ?
O25A N24 O22 109(3) . . ?
O23 N24 O22 117.17(17) . . ?
O102 N100 O103 122.1(2) . . ?
O102 N100 O101 121.1(2) . . ?
O103 N100 O101 116.8(2) . . ?

_refine_diff_density_max         0.545
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.067

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_twin5
_database_code_depnum_ccdc_archive 'CCDC 1010927'
_audit_update_record             
;
2014-06-28 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 Cl Cu N5 O7'
_chemical_formula_weight         469.34

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'
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'

_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                   22.6374(13)
_cell_length_b                   6.6010(4)
_cell_length_c                   12.4456(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.759(2)
_cell_angle_gamma                90
_cell_volume                     1842.71(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    179(2)
_cell_measurement_reflns_used    268
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      50.90

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_F_000             964
_exptl_transmission_factor_min   0.6743
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.380
_shelx_estimated_absorpt_T_min   0.874
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      179(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3871
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.724
_diffrn_reflns_theta_max         27.554
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             3871
_reflns_number_gt                3487
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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 Smart'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Platon (Spek, 2008)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 Refined as a 2-component 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)+(0.0254P)²+2.2420P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3871
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.0839
_refine_ls_wR_factor_gt          0.0792
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_restrained_S_all      1.202
_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 0.24786(2) 0.32097(6) 0.26120(4) 0.01681(10) Uani 1 1 d . . . . .
Cl Cl -0.00615(4) -0.2560(2) 0.37437(9) 0.0357(2) Uani 1 1 d . . . . .
O1 O 0.20436(12) 0.0898(4) 0.21587(19) 0.0213(6) Uani 1 1 d . . . . .
C2 C 0.15759(16) 0.0225(5) 0.2570(3) 0.0187(7) Uani 1 1 d . . . . .
C3 C 0.13303(17) -0.1635(6) 0.2156(3) 0.0220(8) Uani 1 1 d . . . . .
H3 H 0.1517 -0.2320 0.1621 0.026 Uiso 1 1 calc R U . . .
C4 C 0.08369(15) -0.2488(7) 0.2493(3) 0.0254(7) Uani 1 1 d . . . . .
H4 H 0.0680 -0.3725 0.2187 0.030 Uiso 1 1 calc R U . . .
C5 C 0.05682(17) -0.1506(6) 0.3295(3) 0.0249(9) Uani 1 1 d . . . . .
C6 C 0.07959(16) 0.0277(6) 0.3738(3) 0.0223(8) Uani 1 1 d . . . . .
H6 H 0.0611 0.0902 0.4294 0.027 Uiso 1 1 calc R U . . .
C7 C 0.12966(16) 0.1206(5) 0.3390(3) 0.0181(7) Uani 1 1 d . . . . .
C8 C 0.15137(16) 0.3103(5) 0.3916(3) 0.0179(7) Uani 1 1 d . . . . .
C9 C 0.11503(17) 0.4055(6) 0.4712(3) 0.0248(8) Uani 1 1 d . . . . .
H9A H 0.1250 0.5497 0.4792 0.030 Uiso 1 1 calc R U . . .
H9B H 0.1240 0.3380 0.5416 0.030 Uiso 1 1 calc R U . . .
H9C H 0.0725 0.3907 0.4444 0.030 Uiso 1 1 calc R U . . .
N10 N 0.20064(14) 0.3933(4) 0.3723(2) 0.0158(6) Uani 1 1 d . . . . .
C11 C 0.22572(17) 0.5722(6) 0.4341(3) 0.0219(8) Uani 1 1 d . . . . .
H11A H 0.2140 0.5709 0.5079 0.026 Uiso 1 1 calc R U . . .
H11B H 0.2104 0.6982 0.3972 0.026 Uiso 1 1 calc R U . . .
C12 C 0.29291(17) 0.5634(6) 0.4406(3) 0.0210(8) Uani 1 1 d . . . . .
H12A H 0.3103 0.6940 0.4682 0.025 Uiso 1 1 calc R U . . .
H12B H 0.3087 0.4554 0.4917 0.025 Uiso 1 1 calc R U . . .
N13 N 0.31041(13) 0.5215(4) 0.3310(2) 0.0173(6) Uani 1 1 d . . . . .
C14 C 0.36938(16) 0.4178(6) 0.3404(3) 0.0218(8) Uani 1 1 d . . . . .
H14A H 0.3760 0.3681 0.2680 0.026 Uiso 1 1 calc R U . . .
H14B H 0.3686 0.2986 0.3885 0.026 Uiso 1 1 calc R U . . .
C15 C 0.42084(17) 0.5523(6) 0.3846(3) 0.0271(9) Uani 1 1 d . . . . .
H15A H 0.4166 0.5946 0.4595 0.033 Uiso 1 1 calc R U . . .
H15B H 0.4588 0.4773 0.3865 0.033 Uiso 1 1 calc R U . . .
N16 N 0.42140(13) 0.7341(6) 0.3138(3) 0.0283(7) Uani 1 1 d . . . . .
H16A H 0.4546 0.8243 0.3433 0.034 Uiso 1 1 calc R U . . .
H16B H 0.4283 0.6913 0.2403 0.034 Uiso 1 1 calc R U . . .
C17 C 0.36421(17) 0.8470(6) 0.3066(3) 0.0258(9) Uani 1 1 d . . . . .
H17A H 0.3651 0.9636 0.2568 0.031 Uiso 1 1 calc R U . . .
H17B H 0.3588 0.9000 0.3791 0.031 Uiso 1 1 calc R U . . .
C18 C 0.31266(17) 0.7094(5) 0.2655(3) 0.0216(8) Uani 1 1 d . . . . .
H18A H 0.2749 0.7849 0.2658 0.026 Uiso 1 1 calc R U . . .
H18B H 0.3158 0.6715 0.1895 0.026 Uiso 1 1 calc R U . . .
O19 O 0.29176(11) 0.2940(3) 0.1314(2) 0.0222(6) Uani 1 1 d . . . . .
O20 O 0.21963(13) 0.5021(4) 0.0806(2) 0.0310(7) Uani 1 1 d . . . . .
O22 O 0.28348(14) 0.4293(4) -0.0297(2) 0.0324(7) Uani 1 1 d . . . . .
N21 N 0.26445(14) 0.4118(5) 0.0582(2) 0.0219(7) Uani 1 1 d . . . . .
N100 N 0.55674(15) 0.9856(6) 0.4160(3) 0.0327(8) Uani 1 1 d . . . . .
O101 O 0.55349(17) 0.8842(6) 0.4972(3) 0.0594(11) Uani 1 1 d . . . . .
O102 O 0.59063(14) 1.1340(5) 0.4177(2) 0.0385(8) Uani 1 1 d . . . . .
O103 O 0.52605(16) 0.9439(7) 0.3284(3) 0.0734(14) 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 O1 1.862(3) . ?
Cu N10 1.919(3) . ?
Cu O19 2.016(3) . ?
Cu N13 2.044(3) . ?
Cl C5 1.744(4) . ?
O1 C2 1.314(4) . ?
C2 C3 1.416(5) . ?
C2 C7 1.426(5) . ?
C3 C4 1.366(5) . ?
C4 C5 1.397(5) . ?
C5 C6 1.371(5) . ?
C6 C7 1.407(5) . ?
C7 C8 1.467(5) . ?
C8 N10 1.294(4) . ?
C8 C9 1.507(5) . ?
N10 C11 1.480(4) . ?
C11 C12 1.513(5) . ?
C12 N13 1.497(5) . ?
N13 C18 1.489(4) . ?
N13 C14 1.491(5) . ?
C14 C15 1.508(5) . ?
C15 N16 1.490(5) . ?
N16 C17 1.486(5) . ?
C17 C18 1.512(5) . ?
O19 N21 1.290(4) . ?
O20 N21 1.240(4) . ?
O22 N21 1.234(4) . ?
N100 O101 1.223(5) . ?
N100 O103 1.242(5) . ?
N100 O102 1.242(4) . ?

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 N10 95.68(11) . . ?
O1 Cu O19 89.00(10) . . ?
N10 Cu O19 169.26(12) . . ?
O1 Cu N13 165.25(12) . . ?
N10 Cu N13 87.37(12) . . ?
O19 Cu N13 90.54(11) . . ?
C2 O1 Cu 125.4(2) . . ?
O1 C2 C3 116.7(3) . . ?
O1 C2 C7 125.7(3) . . ?
C3 C2 C7 117.6(3) . . ?
C4 C3 C2 122.9(4) . . ?
C3 C4 C5 118.7(4) . . ?
C6 C5 C4 120.6(4) . . ?
C6 C5 Cl 119.5(3) . . ?
C4 C5 Cl 119.8(3) . . ?
C5 C6 C7 121.7(3) . . ?
C6 C7 C2 118.4(3) . . ?
C6 C7 C8 118.0(3) . . ?
C2 C7 C8 123.5(3) . . ?
N10 C8 C7 121.6(3) . . ?
N10 C8 C9 120.4(3) . . ?
C7 C8 C9 118.0(3) . . ?
C8 N10 C11 121.4(3) . . ?
C8 N10 Cu 127.4(2) . . ?
C11 N10 Cu 111.2(2) . . ?
N10 C11 C12 108.0(3) . . ?
N13 C12 C11 110.3(3) . . ?
C18 N13 C14 109.2(3) . . ?
C18 N13 C12 112.2(3) . . ?
C14 N13 C12 110.9(3) . . ?
C18 N13 Cu 112.3(2) . . ?
C14 N13 Cu 107.3(2) . . ?
C12 N13 Cu 104.7(2) . . ?
N13 C14 C15 113.5(3) . . ?
N16 C15 C14 109.0(3) . . ?
C17 N16 C15 111.3(3) . . ?
N16 C17 C18 110.2(3) . . ?
N13 C18 C17 113.4(3) . . ?
N21 O19 Cu 105.77(19) . . ?
O22 N21 O20 123.3(3) . . ?
O22 N21 O19 119.4(3) . . ?
O20 N21 O19 117.3(3) . . ?
O101 N100 O103 121.0(4) . . ?
O101 N100 O102 121.5(4) . . ?
O103 N100 O102 117.4(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N10 Cu O1 C2 0.0(3) . . . . ?
O19 Cu O1 C2 -170.3(3) . . . . ?
N13 Cu O1 C2 101.4(5) . . . . ?
Cu O1 C2 C3 -176.1(2) . . . . ?
Cu O1 C2 C7 4.0(5) . . . . ?
O1 C2 C3 C4 -178.5(4) . . . . ?
C7 C2 C3 C4 1.3(5) . . . . ?
C2 C3 C4 C5 -1.3(6) . . . . ?
C3 C4 C5 C6 -0.1(6) . . . . ?
C3 C4 C5 Cl -179.9(3) . . . . ?
C4 C5 C6 C7 1.4(6) . . . . ?
Cl C5 C6 C7 -178.9(3) . . . . ?
C5 C6 C7 C2 -1.3(5) . . . . ?
C5 C6 C7 C8 -179.4(3) . . . . ?
O1 C2 C7 C6 179.8(3) . . . . ?
C3 C2 C7 C6 -0.1(5) . . . . ?
O1 C2 C7 C8 -2.2(6) . . . . ?
C3 C2 C7 C8 178.0(3) . . . . ?
C6 C7 C8 N10 172.6(3) . . . . ?
C2 C7 C8 N10 -5.4(5) . . . . ?
C6 C7 C8 C9 -6.3(5) . . . . ?
C2 C7 C8 C9 175.6(3) . . . . ?
C7 C8 N10 C11 -173.3(3) . . . . ?
C9 C8 N10 C11 5.6(5) . . . . ?
C7 C8 N10 Cu 10.4(5) . . . . ?
C9 C8 N10 Cu -170.7(3) . . . . ?
C8 N10 C11 C12 149.3(3) . . . . ?
Cu N10 C11 C12 -33.8(4) . . . . ?
N10 C11 C12 N13 47.9(4) . . . . ?
C11 C12 N13 C18 84.5(4) . . . . ?
C11 C12 N13 C14 -153.0(3) . . . . ?
C11 C12 N13 Cu -37.6(3) . . . . ?
C18 N13 C14 C15 54.4(4) . . . . ?
C12 N13 C14 C15 -69.7(4) . . . . ?
Cu N13 C14 C15 176.5(2) . . . . ?
N13 C14 C15 N16 -57.4(4) . . . . ?
C14 C15 N16 C17 57.9(4) . . . . ?
C15 N16 C17 C18 -57.0(4) . . . . ?
C14 N13 C18 C17 -52.8(4) . . . . ?
C12 N13 C18 C17 70.6(4) . . . . ?
Cu N13 C18 C17 -171.8(2) . . . . ?
N16 C17 C18 N13 55.0(4) . . . . ?
Cu O19 N21 O22 177.8(2) . . . . ?
Cu O19 N21 O20 -2.5(3) . . . . ?

_refine_diff_density_max         0.812
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.098

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_f
_database_code_depnum_ccdc_archive 'CCDC 1010928'
_audit_update_record             
;
2014-06-28 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H18 Cl Cu N5 O7'
_chemical_formula_weight         455.31

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'
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'

_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                   22.0294(6)
_cell_length_b                   6.6638(2)
_cell_length_c                   12.1691(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.658(2)
_cell_angle_gamma                90
_cell_volume                     1766.06(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    244
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      51.20

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_F_000             932
_exptl_transmission_factor_min   0.5787
_exptl_transmission_factor_max   0.7461
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.437
_shelx_estimated_absorpt_T_min   0.597
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16648
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.870
_diffrn_reflns_theta_max         30.541
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5396
_reflns_number_gt                4483
_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 Smart'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Platon (Spek, 2008)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.0358P)²+1.1348P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5396
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0843
_refine_ls_wR_factor_gt          0.0797
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.26417(2) 0.66324(3) 0.25848(2) 0.01703(6) Uani 1 1 d . . . . .
Cl Cl 0.49673(3) 1.30962(10) 0.09943(5) 0.04427(15) Uani 1 1 d . . . . .
O1 O 0.31308(6) 0.8836(2) 0.31378(11) 0.0242(3) Uani 1 1 d . . . . .
C2 C 0.35556(8) 0.9679(3) 0.26436(14) 0.0200(3) Uani 1 1 d . . . . .
C3 C 0.37716(8) 0.8891(3) 0.16850(14) 0.0199(3) Uani 1 1 d . . . . .
C4 C 0.42137(8) 0.9969(3) 0.11960(16) 0.0255(4) Uani 1 1 d . . . . .
H4 H 0.4355 0.9452 0.0552 0.031 Uiso 1 1 calc R U . . .
C5 C 0.44408(9) 1.1747(3) 0.16392(16) 0.0263(4) Uani 1 1 d . . . . .
C6 C 0.42497(9) 1.2527(3) 0.25945(16) 0.0264(4) Uani 1 1 d . . . . .
H6 H 0.4418 1.3749 0.2907 0.032 Uiso 1 1 calc R U . . .
C7 C 0.38154(9) 1.1511(3) 0.30810(16) 0.0240(4) Uani 1 1 d . . . . .
H7 H 0.3686 1.2054 0.3729 0.029 Uiso 1 1 calc R U . . .
C8 C 0.35435(8) 0.7063(3) 0.11416(15) 0.0209(3) Uani 1 1 d . . . . .
H8 H 0.3725 0.6629 0.0522 0.025 Uiso 1 1 calc R U . . .
N9 N 0.31121(7) 0.5973(2) 0.14330(12) 0.0187(3) Uani 1 1 d . . . . .
C10 C 0.28802(8) 0.4203(3) 0.07919(15) 0.0209(3) Uani 1 1 d . . . . .
H10A H 0.3041 0.2965 0.1181 0.025 Uiso 1 1 calc R U . . .
H10B H 0.3013 0.4228 0.0050 0.025 Uiso 1 1 calc R U . . .
C11 C 0.21821(8) 0.4251(3) 0.06744(14) 0.0195(3) Uani 1 1 d . . . . .
H11A H 0.2019 0.5299 0.0132 0.023 Uiso 1 1 calc R U . . .
H11B H 0.2013 0.2941 0.0394 0.023 Uiso 1 1 calc R U . . .
N12 N 0.19880(6) 0.4690(2) 0.17815(12) 0.0173(3) Uani 1 1 d . . . . .
C13 C 0.13880(8) 0.5762(3) 0.16498(15) 0.0215(3) Uani 1 1 d . . . . .
H13A H 0.1409 0.6936 0.1159 0.026 Uiso 1 1 calc R U . . .
H13B H 0.1318 0.6268 0.2385 0.026 Uiso 1 1 calc R U . . .
C14 C 0.08487(8) 0.4465(3) 0.11691(16) 0.0260(4) Uani 1 1 d . . . . .
H14A H 0.0463 0.5242 0.1124 0.031 Uiso 1 1 calc R U . . .
H14B H 0.0897 0.4026 0.0410 0.031 Uiso 1 1 calc R U . . .
N15 N 0.08240(7) 0.2681(3) 0.19026(14) 0.0269(3) Uani 1 1 d . . . . .
H15A H 0.0757 0.3131 0.2650 0.032 Uiso 1 1 calc R U . . .
H15B H 0.0474 0.1818 0.1594 0.032 Uiso 1 1 calc R U . . .
C16 C 0.14029(8) 0.1499(3) 0.19993(16) 0.0233(4) Uani 1 1 d . . . . .
H16A H 0.1457 0.0968 0.1261 0.028 Uiso 1 1 calc R U . . .
H16B H 0.1380 0.0347 0.2505 0.028 Uiso 1 1 calc R U . . .
C17 C 0.19470(8) 0.2818(3) 0.24476(14) 0.0201(3) Uani 1 1 d . . . . .
H17A H 0.1915 0.3194 0.3224 0.024 Uiso 1 1 calc R U . . .
H17B H 0.2330 0.2035 0.2457 0.024 Uiso 1 1 calc R U . . .
O18 O 0.28569(6) 0.4814(2) 0.43958(11) 0.0280(3) Uani 1 1 d . . . . .
O19 O 0.21517(6) 0.70152(19) 0.38414(10) 0.0219(3) Uani 1 1 d . . . . .
N20 N 0.24210(7) 0.5848(2) 0.46141(12) 0.0214(3) Uani 1 1 d . . . . .
O21 O 0.22333(7) 0.5796(2) 0.55182(11) 0.0297(3) Uani 1 1 d . . . . .
N100 N 0.05913(8) 0.5272(3) 0.42003(15) 0.0317(4) Uani 1 1 d . . . . .
O101 O 0.09455(7) 0.3810(2) 0.42293(12) 0.0344(3) Uani 1 1 d . . . . .
O102 O 0.05472(9) 0.6245(3) 0.50422(17) 0.0549(5) Uani 1 1 d . . . . .
O103 O 0.02833(9) 0.5716(4) 0.32869(15) 0.0678(7) 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 O1 1.8844(13) . ?
Cu N9 1.9154(14) . ?
Cu O19 2.0164(12) . ?
Cu N12 2.0691(14) . ?
Cl C5 1.7444(18) . ?
O1 C2 1.313(2) . ?
C2 C7 1.418(3) . ?
C2 C3 1.425(2) . ?
C3 C4 1.412(2) . ?
C3 C8 1.440(3) . ?
C4 C5 1.366(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(3) . ?
C6 C7 1.376(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 N9 1.287(2) . ?
C8 H8 0.9500 . ?
N9 C10 1.463(2) . ?
C10 C11 1.523(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N12 1.502(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N12 C13 1.490(2) . ?
N12 C17 1.498(2) . ?
C13 C14 1.513(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N15 1.493(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
N15 C16 1.488(2) . ?
N15 H15A 0.9900 . ?
N15 H15B 0.9900 . ?
C16 C17 1.520(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
O18 N20 1.243(2) . ?
O19 N20 1.294(2) . ?
N20 O21 1.2326(19) . ?
N100 O102 1.228(2) . ?
N100 O101 1.245(2) . ?
N100 O103 1.248(2) . ?

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 N9 95.55(6) . . ?
O1 Cu O19 88.46(5) . . ?
N9 Cu O19 173.92(6) . . ?
O1 Cu N12 167.43(6) . . ?
N9 Cu N12 85.73(6) . . ?
O19 Cu N12 91.35(5) . . ?
C2 O1 Cu 125.37(11) . . ?
O1 C2 C7 118.18(16) . . ?
O1 C2 C3 124.48(16) . . ?
C7 C2 C3 117.34(16) . . ?
C4 C3 C2 119.61(17) . . ?
C4 C3 C8 116.88(16) . . ?
C2 C3 C8 123.46(16) . . ?
C5 C4 C3 120.68(18) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.91(17) . . ?
C4 C5 Cl 119.90(15) . . ?
C6 C5 Cl 119.18(15) . . ?
C7 C6 C5 119.46(18) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C2 121.97(17) . . ?
C6 C7 H7 119.0 . . ?
C2 C7 H7 119.0 . . ?
N9 C8 C3 124.87(16) . . ?
N9 C8 H8 117.6 . . ?
C3 C8 H8 117.6 . . ?
C8 N9 C10 121.39(15) . . ?
C8 N9 Cu 125.12(13) . . ?
C10 N9 Cu 113.02(11) . . ?
N9 C10 C11 107.42(14) . . ?
N9 C10 H10A 110.2 . . ?
C11 C10 H10A 110.2 . . ?
N9 C10 H10B 110.2 . . ?
C11 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
N12 C11 C10 109.85(14) . . ?
N12 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
N12 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C13 N12 C17 109.44(13) . . ?
C13 N12 C11 111.38(13) . . ?
C17 N12 C11 111.82(13) . . ?
C13 N12 Cu 107.10(10) . . ?
C17 N12 Cu 111.09(10) . . ?
C11 N12 Cu 105.88(10) . . ?
N12 C13 C14 113.59(15) . . ?
N12 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
N12 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
N15 C14 C13 108.71(15) . . ?
N15 C14 H14A 109.9 . . ?
C13 C14 H14A 109.9 . . ?
N15 C14 H14B 109.9 . . ?
C13 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
C16 N15 C14 111.16(14) . . ?
C16 N15 H15A 109.4 . . ?
C14 N15 H15A 109.4 . . ?
C16 N15 H15B 109.4 . . ?
C14 N15 H15B 109.4 . . ?
H15A N15 H15B 108.0 . . ?
N15 C16 C17 110.04(15) . . ?
N15 C16 H16A 109.7 . . ?
C17 C16 H16A 109.7 . . ?
N15 C16 H16B 109.7 . . ?
C17 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
N12 C17 C16 113.32(14) . . ?
N12 C17 H17A 108.9 . . ?
C16 C17 H17A 108.9 . . ?
N12 C17 H17B 108.9 . . ?
C16 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
N20 O19 Cu 103.65(10) . . ?
O21 N20 O18 123.30(16) . . ?
O21 N20 O19 119.14(16) . . ?
O18 N20 O19 117.55(14) . . ?
O102 N100 O101 121.13(19) . . ?
O102 N100 O103 121.2(2) . . ?
O101 N100 O103 117.71(19) . . ?

_refine_diff_density_max         0.475
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.071

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_f
_database_code_depnum_ccdc_archive 'CCDC 1010929'
_audit_update_record             
;
2014-06-28 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H56 Cl4 Cu2 N6 O25'
_chemical_formula_weight         1169.68

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'
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'

_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                   9.1817(4)
_cell_length_b                   11.7822(5)
_cell_length_c                   22.0042(10)
_cell_angle_alpha                86.723(2)
_cell_angle_beta                 89.312(2)
_cell_angle_gamma                83.934(2)
_cell_volume                     2363.19(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    312
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      51.70

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   0.6495
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.217
_shelx_estimated_absorpt_T_min   0.776
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33459
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.854
_diffrn_reflns_theta_max         29.197
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             12608
_reflns_number_gt                8436
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0590P)²+1.5291P] 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         12608
_refine_ls_number_parameters     729
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1329
_refine_ls_wR_factor_gt          0.1168
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.027
_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 0.92011(4) 0.41732(3) 0.27257(2) 0.03345(10) Uani 1 1 d . . . . .
Cu2 Cu 0.94411(4) 0.16648(3) 0.21921(2) 0.03577(10) Uani 1 1 d . . . . .
O1 O 1.0513(2) 0.30197(15) 0.22972(8) 0.0349(4) Uani 1 1 d . . . . .
C2 C 1.1576(4) 0.3264(2) 0.19071(13) 0.0371(7) Uani 1 1 d . . . . .
C3 C 1.2147(4) 0.2447(3) 0.14938(13) 0.0434(7) Uani 1 1 d . . . . .
C4 C 1.3320(4) 0.2653(3) 0.11178(15) 0.0540(9) Uani 1 1 d . . . . .
H4 H 1.3707 0.2084 0.0853 0.065 Uiso 1 1 calc R U . . .
C5 C 1.3938(5) 0.3674(3) 0.11209(17) 0.0583(10) Uani 1 1 d . . . . .
H5 H 1.4746 0.3803 0.0862 0.070 Uiso 1 1 calc R U . . .
C6 C 1.3380(4) 0.4492(3) 0.14984(16) 0.0531(9) Uani 1 1 d . . . . .
H6 H 1.3794 0.5198 0.1494 0.064 Uiso 1 1 calc R U . . .
C7 C 1.2207(4) 0.4310(3) 0.18935(14) 0.0420(7) Uani 1 1 d . . . . .
O8 O 1.1476(3) 0.14628(18) 0.15138(9) 0.0480(6) Uani 1 1 d . . . . .
C9 C 1.1849(5) 0.0664(3) 0.10437(17) 0.0656(11) Uani 1 1 d . . . . .
H9A H 1.1552 -0.0095 0.1177 0.079 Uiso 1 1 calc R U . A 1
H9B H 1.2922 0.0582 0.0976 0.079 Uiso 1 1 calc R U . A 1
C10A C 1.1088(9) 0.1084(7) 0.0461(3) 0.081(3) Uani 0.594(8) 1 d . . P B 1
H10A H 1.0067 0.1359 0.0548 0.097 Uiso 0.594(8) 1 calc R U P B 1
H10B H 1.1118 0.0456 0.0185 0.097 Uiso 0.594(8) 1 calc R U P B 1
H10C H 1.1583 0.1709 0.0268 0.097 Uiso 0.594(8) 1 calc R U P B 1
C10B C 1.1048(9) -0.0289(8) 0.1063(4) 0.052(3) Uani 0.406(8) 1 d . . P B 2
H10D H 1.1220 -0.0728 0.1452 0.063 Uiso 0.406(8) 1 calc R U P B 2
H10E H 1.1364 -0.0772 0.0728 0.063 Uiso 0.406(8) 1 calc R U P B 2
H10F H 1.0002 -0.0031 0.1022 0.063 Uiso 0.406(8) 1 calc R U P B 2
C11 C 1.1713(4) 0.5229(2) 0.22782(14) 0.0418(7) Uani 1 1 d . . . . .
H11 H 1.2269 0.5867 0.2264 0.050 Uiso 1 1 calc R U . . .
N12 N 1.0615(3) 0.52699(19) 0.26317(11) 0.0372(6) Uani 1 1 d . . . . .
C13 C 1.0291(4) 0.6250(2) 0.30092(16) 0.0476(8) Uani 1 1 d . . . . .
H13A H 1.0648 0.6941 0.2807 0.057 Uiso 1 1 calc R U . . .
H13B H 1.0780 0.6098 0.3408 0.057 Uiso 1 1 calc R U . . .
C14 C 0.8658(4) 0.6429(2) 0.30951(16) 0.0448(8) Uani 1 1 d . . . . .
H14A H 0.8406 0.7002 0.3401 0.054 Uiso 1 1 calc R U . . .
H14B H 0.8184 0.6715 0.2706 0.054 Uiso 1 1 calc R U . . .
N15 N 0.8123(3) 0.53104(18) 0.33051(11) 0.0346(5) Uani 1 1 d . . . . .
C16 C 0.6489(3) 0.5372(3) 0.32592(15) 0.0425(7) Uani 1 1 d . . . . .
H16A H 0.6183 0.4598 0.3349 0.051 Uiso 1 1 calc R U . . .
H16B H 0.6197 0.5616 0.2836 0.051 Uiso 1 1 calc R U . . .
C17 C 0.5691(4) 0.6187(3) 0.36882(16) 0.0476(8) Uani 1 1 d . . . . .
H17A H 0.5919 0.6977 0.3580 0.057 Uiso 1 1 calc R U . . .
H17B H 0.4621 0.6168 0.3650 0.057 Uiso 1 1 calc R U . . .
N18 N 0.6150(3) 0.5853(2) 0.43297(12) 0.0433(6) Uani 1 1 d . . . . .
H18A H 0.5680 0.6425 0.4603 0.052 Uiso 1 1 calc R U . . .
H18B H 0.5806 0.5105 0.4452 0.052 Uiso 1 1 calc R U . . .
C19 C 0.7770(3) 0.5774(2) 0.44042(14) 0.0394(7) Uani 1 1 d . . . . .
H19A H 0.8034 0.5485 0.4824 0.047 Uiso 1 1 calc R U . . .
H19B H 0.8107 0.6542 0.4336 0.047 Uiso 1 1 calc R U . . .
C20 C 0.8513(3) 0.4975(2) 0.39536(13) 0.0352(6) Uani 1 1 d . . . . .
H20A H 0.9587 0.4952 0.3999 0.042 Uiso 1 1 calc R U . . .
H20B H 0.8241 0.4194 0.4053 0.042 Uiso 1 1 calc R U . . .
O21 O 0.8344(3) 0.25475(19) 0.15538(10) 0.0506(6) Uani 1 1 d . . . . .
C22 C 0.7666(4) 0.2110(3) 0.11114(14) 0.0480(8) Uani 1 1 d . . . . .
C23 C 0.7369(5) 0.2800(4) 0.05657(16) 0.0653(11) Uani 1 1 d . . . . .
C24 C 0.6693(5) 0.2373(5) 0.00812(16) 0.0740(13) Uani 1 1 d . . . . .
H24 H 0.6514 0.2838 -0.0283 0.089 Uiso 1 1 calc R U . . .
C25 C 0.6276(4) 0.1276(5) 0.01225(18) 0.0735(14) Uani 1 1 d . . . . .
H25 H 0.5822 0.0991 -0.0215 0.088 Uiso 1 1 calc R U . . .
C26 C 0.6507(4) 0.0613(4) 0.06357(18) 0.0633(11) Uani 1 1 d . . . . .
H26 H 0.6184 -0.0128 0.0662 0.076 Uiso 1 1 calc R U . . .
C27 C 0.7229(4) 0.1003(3) 0.11436(15) 0.0470(8) Uani 1 1 d . . . . .
O28 O 0.7748(4) 0.3879(3) 0.05973(14) 0.1008(13) Uani 1 1 d . . . . .
C29A C 0.7165(17) 0.4896(11) 0.0171(4) 0.079(4) Uani 0.526(16) 1 d . . P C 1
H29A H 0.7625 0.4814 -0.0235 0.095 Uiso 0.526(16) 1 calc R U P C 1
H29B H 0.6095 0.4894 0.0124 0.095 Uiso 0.526(16) 1 calc R U P C 1
C30A C 0.748(2) 0.6029(12) 0.0411(6) 0.120(6) Uani 0.526(16) 1 d . . P C 1
H30A H 0.6764 0.6246 0.0729 0.144 Uiso 0.526(16) 1 calc R U P C 1
H30B H 0.7407 0.6619 0.0077 0.144 Uiso 0.526(16) 1 calc R U P C 1
H30C H 0.8468 0.5952 0.0581 0.144 Uiso 0.526(16) 1 calc R U P C 1
C29B C 0.8010(19) 0.4338(13) -0.0038(6) 0.085(4) Uani 0.474(16) 1 d . . P C 2
H29C H 0.8716 0.3815 -0.0259 0.102 Uiso 0.474(16) 1 calc R U P C 2
H29D H 0.7088 0.4488 -0.0271 0.102 Uiso 0.474(16) 1 calc R U P C 2
C30B C 0.863(2) 0.5413(14) 0.0084(8) 0.125(8) Uani 0.474(16) 1 d . . P C 2
H30D H 0.7949 0.5874 0.0341 0.150 Uiso 0.474(16) 1 calc R U P C 2
H30E H 0.8783 0.5843 -0.0301 0.150 Uiso 0.474(16) 1 calc R U P C 2
H30F H 0.9568 0.5233 0.0294 0.150 Uiso 0.474(16) 1 calc R U P C 2
C31 C 0.7471(4) 0.0246(3) 0.16762(16) 0.0487(8) Uani 1 1 d . . . . .
H31 H 0.7003 -0.0437 0.1695 0.058 Uiso 1 1 calc R U . . .
N32 N 0.8271(3) 0.0419(2) 0.21284(12) 0.0409(6) Uani 1 1 d . . . . .
C33 C 0.8437(4) -0.0399(3) 0.26487(18) 0.0546(9) Uani 1 1 d . . . . .
H33A H 0.8123 -0.1141 0.2543 0.065 Uiso 1 1 calc R U . . .
H33B H 0.7831 -0.0115 0.2994 0.065 Uiso 1 1 calc R U . . .
C34 C 1.0046(4) -0.0540(2) 0.28180(16) 0.0445(8) Uani 1 1 d . . . . .
H34A H 1.0189 -0.1016 0.3203 0.053 Uiso 1 1 calc R U . . .
H34B H 1.0630 -0.0930 0.2495 0.053 Uiso 1 1 calc R U . . .
N35 N 1.0546(3) 0.06112(18) 0.28932(10) 0.0341(5) Uani 1 1 d . . . . .
C36 C 1.0163(4) 0.1031(3) 0.35064(13) 0.0442(8) Uani 1 1 d . . . . .
H36A H 0.9094 0.1027 0.3571 0.053 Uiso 1 1 calc R U . . .
H36B H 1.0390 0.1833 0.3515 0.053 Uiso 1 1 calc R U . . .
C37 C 1.0958(4) 0.0334(3) 0.40302(15) 0.0511(9) Uani 1 1 d . . . . .
H37A H 1.0713 0.0704 0.4416 0.061 Uiso 1 1 calc R U . . .
H37B H 1.0627 -0.0440 0.4064 0.061 Uiso 1 1 calc R U . . .
N38 N 1.2575(3) 0.0238(2) 0.39317(12) 0.0503(7) Uani 1 1 d . . . . .
H38A H 1.3054 -0.0301 0.4248 0.060 Uiso 1 1 calc R U . . .
H38B H 1.2927 0.0995 0.3977 0.060 Uiso 1 1 calc R U . . .
C39 C 1.3010(4) -0.0165(3) 0.33188(14) 0.0472(8) Uani 1 1 d . . . . .
H39A H 1.2809 -0.0970 0.3295 0.057 Uiso 1 1 calc R U . . .
H39B H 1.4073 -0.0129 0.3256 0.057 Uiso 1 1 calc R U . . .
C40 C 1.2168(4) 0.0570(3) 0.28251(14) 0.0417(7) Uani 1 1 d . . . . .
H40A H 1.2450 0.1357 0.2828 0.050 Uiso 1 1 calc R U . . .
H40B H 1.2456 0.0270 0.2425 0.050 Uiso 1 1 calc R U . . .
O41 O 0.7956(2) 0.29237(16) 0.28918(10) 0.0346(5) Uani 1 1 d . . . . .
H41A H 0.713(4) 0.299(3) 0.2677(15) 0.042 Uiso 1 1 d . U . . .
H41B H 0.771(4) 0.282(3) 0.3231(16) 0.042 Uiso 1 1 d . U . . .
O42 O 0.7882(4) 0.4753(2) 0.18978(13) 0.0623(8) Uani 1 1 d . . . . .
H42A H 0.739(5) 0.516(4) 0.180(2) 0.075 Uiso 1 1 d . U . . .
H42B H 0.795(5) 0.434(4) 0.164(2) 0.075 Uiso 1 1 d . U . . .
Cl10 Cl 0.19814(9) 0.70596(6) 0.46043(4) 0.04329(19) Uani 1 1 d . . . . .
O101 O 0.3301(3) 0.64420(19) 0.48608(12) 0.0519(6) Uani 1 1 d . . . . .
O102 O 0.1520(4) 0.7987(2) 0.49700(15) 0.0919(11) Uani 1 1 d . . . . .
O103 O 0.0885(3) 0.6308(2) 0.45917(13) 0.0662(7) Uani 1 1 d . . . . .
O104 O 0.2268(3) 0.7483(3) 0.39961(13) 0.0767(8) Uani 1 1 d . . . . .
Cl20 Cl 1.32237(9) 0.35259(7) 0.38199(4) 0.0476(2) Uani 1 1 d . . . . .
O201 O 1.3982(3) 0.3945(2) 0.43120(11) 0.0604(7) Uani 1 1 d . . . . .
O202 O 1.3506(4) 0.4201(3) 0.32757(13) 0.0835(9) Uani 1 1 d . . . . .
O203 O 1.3825(3) 0.2369(2) 0.37191(15) 0.0739(9) Uani 1 1 d . . . . .
O204 O 1.1702(3) 0.3537(2) 0.39354(15) 0.0751(8) Uani 1 1 d . . . . .
Cl30 Cl 0.33436(10) 1.08944(6) 0.56022(4) 0.0526(2) Uani 0.538(11) 1 d . . P D
1
O301 O 0.2227(4) 1.1338(3) 0.60034(17) 0.1042(13) Uani 0.538(11) 1 d . . P D 1
O302 O 0.295(2) 1.0009(9) 0.5250(6) 0.114(5) Uani 0.538(11) 1 d . . P D 1
O303 O 0.4444(11) 1.0548(17) 0.5920(5) 0.176(8) Uani 0.538(11) 1 d . . P D 1
O304 O 0.3519(10) 1.1799(4) 0.5109(4) 0.096(4) Uani 0.538(11) 1 d . . P D 1
Cl31 Cl 0.33436(10) 1.08944(6) 0.56022(4) 0.0526(2) Uani 0.462(11) 1 d . . P D
2
O305 O 0.2227(4) 1.1338(3) 0.60034(17) 0.1042(13) Uani 0.462(11) 1 d . . P D 2
O306 O 0.4112(14) 0.9867(6) 0.5926(8) 0.138(6) Uani 0.462(11) 1 d . . P D 2
O307 O 0.4551(8) 1.1617(5) 0.5547(4) 0.063(3) Uani 0.462(11) 1 d . . P D 2
O308 O 0.2731(19) 1.0566(18) 0.5129(7) 0.137(8) Uani 0.462(11) 1 d . . P D 2
Cl40 Cl 1.45697(13) 0.78018(10) 0.19247(5) 0.0699(3) Uani 0.574(7) 1 d . . P E
1
O401 O 1.3084(8) 0.7807(6) 0.2098(5) 0.118(4) Uani 0.574(7) 1 d . . P E 1
O402 O 1.5508(8) 0.8110(6) 0.2408(3) 0.098(3) Uani 0.574(7) 1 d . . P E 1
O403 O 1.5215(8) 0.6596(5) 0.1847(4) 0.115(3) Uani 0.574(7) 1 d . . P E 1
O404 O 1.4828(8) 0.8389(8) 0.1397(3) 0.110(3) Uani 0.574(7) 1 d . . P E 1
Cl41 Cl 1.45697(13) 0.78018(10) 0.19247(5) 0.0699(3) Uani 0.426(7) 1 d . . P E
2
O405 O 1.4478(9) 0.9020(7) 0.1955(6) 0.116(5) Uani 0.426(7) 1 d . . P E 2
O406 O 1.428(2) 0.7241(11) 0.2399(5) 0.161(7) Uani 0.426(7) 1 d . . P E 2
O407 O 1.566(4) 0.7461(16) 0.1679(15) 0.42(3) Uani 0.426(7) 1 d . . P E 2
O408 O 1.366(4) 0.7474(16) 0.1500(9) 0.320(18) Uani 0.426(7) 1 d . . P E 2
O100 O 0.6932(3) 0.2254(2) 0.39291(12) 0.0568(6) Uani 1 1 d D . . . .
H10G H 0.736(4) 0.205(3) 0.4252(10) 0.068 Uiso 1 1 d D U . . .
H10H H 0.6044(14) 0.220(4) 0.3955(19) 0.068 Uiso 1 1 d D U . . .
O200 O 0.5386(3) 0.2639(3) 0.24436(12) 0.0699(8) Uani 1 1 d . . . . .
O300 O 1.0589(17) -0.2181(13) 0.0998(7) 0.214(6) Uani 0.5 1 d . . P . .
O400 O 0.8153(13) 0.6918(8) 0.1481(5) 0.153(4) Uani 0.5 1 d . . P . .


_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 N12 1.928(2) . ?
Cu1 O41 1.973(2) . ?
Cu1 O1 1.990(2) . ?
Cu1 N15 2.070(2) . ?
Cu1 O42 2.233(3) . ?
Cu2 N32 1.921(2) . ?
Cu2 O21 1.927(2) . ?
Cu2 O1 1.9875(18) . ?
Cu2 N35 2.122(2) . ?
Cu2 O8 2.378(2) . ?
O1 C2 1.336(4) . ?
C2 C7 1.415(4) . ?
C2 C3 1.418(4) . ?
C3 O8 1.368(4) . ?
C3 C4 1.384(5) . ?
C4 C5 1.384(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.363(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.403(5) . ?
C6 H6 0.9500 . ?
C7 C11 1.444(4) . ?
O8 C9 1.451(4) . ?
C9 C10B 1.404(9) . ?
C9 C10A 1.501(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
C11 N12 1.264(4) . ?
C11 H11 0.9500 . ?
N12 C13 1.464(4) . ?
C13 C14 1.502(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N15 1.501(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
N15 C20 1.496(4) . ?
N15 C16 1.498(4) . ?
C16 C17 1.513(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 N18 1.497(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
N18 C19 1.490(4) . ?
N18 H18A 0.9900 . ?
N18 H18B 0.9900 . ?
C19 C20 1.513(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
O21 C22 1.319(4) . ?
C22 C27 1.403(5) . ?
C22 C23 1.423(5) . ?
C23 O28 1.359(5) . ?
C23 C24 1.385(5) . ?
C24 C25 1.384(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.342(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.429(4) . ?
C26 H26 0.9500 . ?
C27 C31 1.436(5) . ?
O28 C29B 1.495(11) . ?
O28 C29A 1.533(11) . ?
C29A C30A 1.519(16) . ?
C29A H29A 0.9900 . ?
C29A H29B 0.9900 . ?
C30A H30A 0.9800 . ?
C30A H30B 0.9800 . ?
C30A H30C 0.9800 . ?
C29B C30B 1.481(17) . ?
C29B H29C 0.9900 . ?
C29B H29D 0.9900 . ?
C30B H30D 0.9800 . ?
C30B H30E 0.9800 . ?
C30B H30F 0.9800 . ?
C31 N32 1.282(4) . ?
C31 H31 0.9500 . ?
N32 C33 1.453(4) . ?
C33 C34 1.517(5) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 N35 1.496(3) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
N35 C36 1.489(4) . ?
N35 C40 1.491(4) . ?
C36 C37 1.524(4) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 N38 1.491(5) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
N38 C39 1.491(4) . ?
N38 H38A 0.9900 . ?
N38 H38B 0.9900 . ?
C39 C40 1.516(4) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
O41 H41A 0.89(4) . ?
O41 H41B 0.78(3) . ?
O42 H42A 0.65(5) . ?
O42 H42B 0.76(4) . ?
Cl10 O103 1.411(3) . ?
Cl10 O102 1.420(3) . ?
Cl10 O104 1.432(3) . ?
Cl10 O101 1.449(2) . ?
Cl20 O204 1.416(3) . ?
Cl20 O201 1.433(2) . ?
Cl20 O202 1.436(3) . ?
Cl20 O203 1.444(3) . ?
Cl30 O303 1.254(8) . ?
Cl30 O302 1.414(12) . ?
Cl30 O301 1.422(3) . ?
Cl30 O304 1.497(6) . ?
Cl31 O308 1.287(12) . ?
Cl31 O305 1.422(3) . ?
Cl31 O307 1.467(6) . ?
Cl31 O306 1.484(10) . ?
Cl40 O404 1.348(6) . ?
Cl40 O401 1.412(6) . ?
Cl40 O402 1.462(6) . ?
Cl40 O403 1.498(6) . ?
Cl41 O407 1.179(19) . ?
Cl41 O406 1.244(10) . ?
Cl41 O408 1.362(12) . ?
Cl41 O405 1.435(9) . ?
O100 H10G 0.828(10) . ?
O100 H10H 0.825(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
N12 Cu1 O41 172.15(10) . . ?
N12 Cu1 O1 91.35(9) . . ?
O41 Cu1 O1 85.24(8) . . ?
N12 Cu1 N15 85.24(10) . . ?
O41 Cu1 N15 96.80(9) . . ?
O1 Cu1 N15 169.04(9) . . ?
N12 Cu1 O42 97.38(11) . . ?
O41 Cu1 O42 89.92(11) . . ?
O1 Cu1 O42 94.08(10) . . ?
N15 Cu1 O42 96.69(11) . . ?
N32 Cu2 O21 91.24(10) . . ?
N32 Cu2 O1 175.16(10) . . ?
O21 Cu2 O1 87.77(9) . . ?
N32 Cu2 N35 84.96(10) . . ?
O21 Cu2 N35 176.17(9) . . ?
O1 Cu2 N35 95.97(8) . . ?
N32 Cu2 O8 110.08(9) . . ?
O21 Cu2 O8 88.57(10) . . ?
O1 Cu2 O8 74.63(8) . . ?
N35 Cu2 O8 93.19(9) . . ?
C2 O1 Cu2 120.19(16) . . ?
C2 O1 Cu1 124.83(16) . . ?
Cu2 O1 Cu1 108.46(10) . . ?
O1 C2 C7 122.8(3) . . ?
O1 C2 C3 120.0(3) . . ?
C7 C2 C3 117.2(3) . . ?
O8 C3 C4 124.3(3) . . ?
O8 C3 C2 114.9(3) . . ?
C4 C3 C2 120.7(3) . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C7 121.2(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C2 120.2(3) . . ?
C6 C7 C11 116.6(3) . . ?
C2 C7 C11 123.2(3) . . ?
C3 O8 C9 117.8(3) . . ?
C3 O8 Cu2 108.73(18) . . ?
C9 O8 Cu2 131.3(2) . . ?
C10B C9 O8 115.2(5) . . ?
O8 C9 C10A 110.2(4) . . ?
O8 C9 H9A 109.6 . . ?
C10A C9 H9A 109.6 . . ?
O8 C9 H9B 109.6 . . ?
C10A C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C9 C10A H10A 109.5 . . ?
C9 C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
C9 C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C9 C10B H10D 109.5 . . ?
C9 C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
C9 C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
N12 C11 C7 126.4(3) . . ?
N12 C11 H11 116.8 . . ?
C7 C11 H11 116.8 . . ?
C11 N12 C13 119.7(2) . . ?
C11 N12 Cu1 127.0(2) . . ?
C13 N12 Cu1 113.2(2) . . ?
N12 C13 C14 107.6(2) . . ?
N12 C13 H13A 110.2 . . ?
C14 C13 H13A 110.2 . . ?
N12 C13 H13B 110.2 . . ?
C14 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?
N15 C14 C13 108.8(2) . . ?
N15 C14 H14A 109.9 . . ?
C13 C14 H14A 109.9 . . ?
N15 C14 H14B 109.9 . . ?
C13 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
C20 N15 C16 107.2(2) . . ?
C20 N15 C14 112.3(2) . . ?
C16 N15 C14 110.9(2) . . ?
C20 N15 Cu1 110.72(17) . . ?
C16 N15 Cu1 112.94(17) . . ?
C14 N15 Cu1 102.93(18) . . ?
N15 C16 C17 113.3(2) . . ?
N15 C16 H16A 108.9 . . ?
C17 C16 H16A 108.9 . . ?
N15 C16 H16B 108.9 . . ?
C17 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
N18 C17 C16 109.8(3) . . ?
N18 C17 H17A 109.7 . . ?
C16 C17 H17A 109.7 . . ?
N18 C17 H17B 109.7 . . ?
C16 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C19 N18 C17 112.2(2) . . ?
C19 N18 H18A 109.2 . . ?
C17 N18 H18A 109.2 . . ?
C19 N18 H18B 109.2 . . ?
C17 N18 H18B 109.2 . . ?
H18A N18 H18B 107.9 . . ?
N18 C19 C20 109.8(2) . . ?
N18 C19 H19A 109.7 . . ?
C20 C19 H19A 109.7 . . ?
N18 C19 H19B 109.7 . . ?
C20 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
N15 C20 C19 113.7(2) . . ?
N15 C20 H20A 108.8 . . ?
C19 C20 H20A 108.8 . . ?
N15 C20 H20B 108.8 . . ?
C19 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C22 O21 Cu2 124.8(2) . . ?
O21 C22 C27 124.0(3) . . ?
O21 C22 C23 118.1(3) . . ?
C27 C22 C23 117.9(3) . . ?
O28 C23 C24 126.3(4) . . ?
O28 C23 C22 113.1(3) . . ?
C24 C23 C22 120.5(4) . . ?
C23 C24 C25 120.6(4) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C26 C25 C24 120.5(4) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C27 121.1(4) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
C22 C27 C26 119.4(4) . . ?
C22 C27 C31 122.0(3) . . ?
C26 C27 C31 118.6(3) . . ?
C23 O28 C29B 107.8(6) . . ?
C23 O28 C29A 124.4(5) . . ?
C30A C29A O28 112.0(7) . . ?
C30A C29A H29A 109.2 . . ?
O28 C29A H29A 109.2 . . ?
C30A C29A H29B 109.2 . . ?
O28 C29A H29B 109.2 . . ?
H29A C29A H29B 107.9 . . ?
C29A C30A H30A 109.5 . . ?
C29A C30A H30B 109.5 . . ?
H30A C30A H30B 109.5 . . ?
C29A C30A H30C 109.5 . . ?
H30A C30A H30C 109.5 . . ?
H30B C30A H30C 109.5 . . ?
C30B C29B O28 100.7(9) . . ?
C30B C29B H29C 111.6 . . ?
O28 C29B H29C 111.6 . . ?
C30B C29B H29D 111.6 . . ?
O28 C29B H29D 111.6 . . ?
H29C C29B H29D 109.4 . . ?
C29B C30B H30D 109.5 . . ?
C29B C30B H30E 109.5 . . ?
H30D C30B H30E 109.5 . . ?
C29B C30B H30F 109.5 . . ?
H30D C30B H30F 109.5 . . ?
H30E C30B H30F 109.5 . . ?
N32 C31 C27 125.1(3) . . ?
N32 C31 H31 117.4 . . ?
C27 C31 H31 117.4 . . ?
C31 N32 C33 120.8(3) . . ?
C31 N32 Cu2 126.5(2) . . ?
C33 N32 Cu2 112.6(2) . . ?
N32 C33 C34 107.1(3) . . ?
N32 C33 H33A 110.3 . . ?
C34 C33 H33A 110.3 . . ?
N32 C33 H33B 110.3 . . ?
C34 C33 H33B 110.3 . . ?
H33A C33 H33B 108.5 . . ?
N35 C34 C33 109.3(2) . . ?
N35 C34 H34A 109.8 . . ?
C33 C34 H34A 109.8 . . ?
N35 C34 H34B 109.8 . . ?
C33 C34 H34B 109.8 . . ?
H34A C34 H34B 108.3 . . ?
C36 N35 C40 107.2(2) . . ?
C36 N35 C34 111.7(2) . . ?
C40 N35 C34 110.9(2) . . ?
C36 N35 Cu2 111.67(18) . . ?
C40 N35 Cu2 111.74(17) . . ?
C34 N35 Cu2 103.83(18) . . ?
N35 C36 C37 114.4(3) . . ?
N35 C36 H36A 108.7 . . ?
C37 C36 H36A 108.7 . . ?
N35 C36 H36B 108.7 . . ?
C37 C36 H36B 108.7 . . ?
H36A C36 H36B 107.6 . . ?
N38 C37 C36 110.9(3) . . ?
N38 C37 H37A 109.5 . . ?
C36 C37 H37A 109.5 . . ?
N38 C37 H37B 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 108.0 . . ?
C37 N38 C39 112.4(3) . . ?
C37 N38 H38A 109.1 . . ?
C39 N38 H38A 109.1 . . ?
C37 N38 H38B 109.1 . . ?
C39 N38 H38B 109.1 . . ?
H38A N38 H38B 107.8 . . ?
N38 C39 C40 110.5(3) . . ?
N38 C39 H39A 109.6 . . ?
C40 C39 H39A 109.6 . . ?
N38 C39 H39B 109.6 . . ?
C40 C39 H39B 109.6 . . ?
H39A C39 H39B 108.1 . . ?
N35 C40 C39 113.8(2) . . ?
N35 C40 H40A 108.8 . . ?
C39 C40 H40A 108.8 . . ?
N35 C40 H40B 108.8 . . ?
C39 C40 H40B 108.8 . . ?
H40A C40 H40B 107.7 . . ?
Cu1 O41 H41A 115(2) . . ?
Cu1 O41 H41B 116(3) . . ?
H41A O41 H41B 105(3) . . ?
Cu1 O42 H42A 141(5) . . ?
Cu1 O42 H42B 115(4) . . ?
H42A O42 H42B 104(6) . . ?
O103 Cl10 O102 110.2(2) . . ?
O103 Cl10 O104 109.18(18) . . ?
O102 Cl10 O104 109.7(2) . . ?
O103 Cl10 O101 108.90(15) . . ?
O102 Cl10 O101 109.04(16) . . ?
O104 Cl10 O101 109.73(17) . . ?
O204 Cl20 O201 112.35(18) . . ?
O204 Cl20 O202 111.4(2) . . ?
O201 Cl20 O202 108.22(17) . . ?
O204 Cl20 O203 108.79(17) . . ?
O201 Cl20 O203 109.34(17) . . ?
O202 Cl20 O203 106.6(2) . . ?
O303 Cl30 O302 110.2(10) . . ?
O303 Cl30 O301 107.3(5) . . ?
O302 Cl30 O301 114.7(8) . . ?
O303 Cl30 O304 117.6(9) . . ?
O302 Cl30 O304 99.9(5) . . ?
O301 Cl30 O304 107.4(3) . . ?
O308 Cl31 O305 108.4(8) . . ?
O308 Cl31 O307 121.4(9) . . ?
O305 Cl31 O307 111.9(3) . . ?
O308 Cl31 O306 107.8(10) . . ?
O305 Cl31 O306 106.5(7) . . ?
O307 Cl31 O306 99.6(5) . . ?
O404 Cl40 O401 115.7(6) . . ?
O404 Cl40 O402 110.7(4) . . ?
O401 Cl40 O402 113.6(5) . . ?
O404 Cl40 O403 106.0(6) . . ?
O401 Cl40 O403 109.4(4) . . ?
O402 Cl40 O403 99.9(4) . . ?
O407 Cl41 O406 114.9(18) . . ?
O407 Cl41 O408 96(2) . . ?
O406 Cl41 O408 104.4(10) . . ?
O407 Cl41 O405 110.2(8) . . ?
O406 Cl41 O405 117.0(9) . . ?
O408 Cl41 O405 112.5(11) . . ?
H10G O100 H10H 112(4) . . ?

_refine_diff_density_max         0.775
_refine_diff_density_min         -0.801
_refine_diff_density_rms         0.076

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_sk_73
_database_code_depnum_ccdc_archive 'CCDC 1401268'
_audit_update_record             
;
2015-05-16 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H21 Cu N5 O8, C H4 O'
_chemical_formula_sum            'C15 H25 Cu N5 O9'
_chemical_formula_weight         482.95

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   12.0035(5)
_cell_length_b                   9.5610(4)
_cell_length_c                   18.1151(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.715(3)
_cell_angle_gamma                90.00
_cell_volume                     2001.28(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1004
_exptl_absorpt_coefficient_mu    1.151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_T_max  0.891
_exptl_absorpt_process_details   SADABAS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18964
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_sigmaI/netI    0.0673
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         27.31
_reflns_number_total             4521
_reflns_number_gt                2859
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SMART APEX II'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0654P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4521
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1307
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_restrained_S_all      0.965
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.007

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.19784(3) 0.73704(4) -0.01178(2) 0.03484(16) Uani 1 1 d . . .
O1 O 0.20404(19) 0.5309(2) -0.00084(13) 0.0439(6) Uani 1 1 d . . .
O2 O 0.2941(3) 0.3592(3) -0.0341(2) 0.0998(12) Uani 1 1 d . . .
O3 O 0.3002(2) 0.5605(3) -0.08450(16) 0.0679(8) Uani 1 1 d . . .
O4 O 0.3465(2) 0.7457(2) 0.06146(14) 0.0445(6) Uani 1 1 d . . .
O5 O 0.71643(19) 0.9305(3) 0.18877(14) 0.0594(8) Uani 1 1 d . . .
O6 O 0.1694(2) 0.8978(3) 0.15220(16) 0.0636(8) Uani 1 1 d . . .
O7 O 0.1538(3) 0.7182(3) 0.21631(16) 0.0835(10) Uani 1 1 d . . .
O8 O 0.1054(2) 0.7045(3) 0.09423(14) 0.0614(8) Uani 1 1 d . . .
O9 O -0.3812(2) 0.4472(3) -0.17648(14) 0.0548(7) Uani 1 1 d . . .
H9 H -0.3626 0.3949 -0.1393 0.082 Uiso 1 1 calc R . .
N1 N 0.2685(3) 0.4816(4) -0.04049(19) 0.0540(9) Uani 1 1 d . . .
N2 N 0.1911(2) 0.9342(3) -0.02924(14) 0.0355(6) Uani 1 1 d . . .
N3 N 0.0429(2) 0.7295(3) -0.10162(14) 0.0333(6) Uani 1 1 d . . .
N4 N -0.1746(2) 0.5918(3) -0.18138(15) 0.0450(8) Uani 1 1 d . . .
H4A H -0.2425 0.5931 -0.2179 0.054 Uiso 1 1 calc R . .
H4B H -0.1690 0.5092 -0.1568 0.054 Uiso 1 1 calc R . .
N5 N 0.1425(2) 0.7740(4) 0.15378(17) 0.0434(8) Uani 1 1 d . . .
C1 C 0.0852(3) 0.9817(4) -0.08463(18) 0.0391(8) Uani 1 1 d . . .
H1A H 0.1003 1.0659 -0.1103 0.047 Uiso 1 1 calc R . .
H1B H 0.0261 1.0024 -0.0588 0.047 Uiso 1 1 calc R . .
C2 C 0.0458(3) 0.8666(4) -0.14152(18) 0.0390(8) Uani 1 1 d . . .
H2A H -0.0308 0.8879 -0.1740 0.047 Uiso 1 1 calc R . .
H2B H 0.0980 0.8595 -0.1739 0.047 Uiso 1 1 calc R . .
C3 C 0.0353(3) 0.6105(4) -0.15600(18) 0.0409(9) Uani 1 1 d . . .
H3A H 0.0456 0.5236 -0.1273 0.049 Uiso 1 1 calc R . .
H3B H 0.0979 0.6182 -0.1801 0.049 Uiso 1 1 calc R . .
C4 C -0.0784(3) 0.6046(4) -0.21781(18) 0.0426(9) Uani 1 1 d . . .
H4C H -0.0882 0.6889 -0.2487 0.051 Uiso 1 1 calc R . .
H4D H -0.0787 0.5250 -0.2511 0.051 Uiso 1 1 calc R . .
C5 C -0.1731(3) 0.7064(4) -0.12616(19) 0.0417(9) Uani 1 1 d . . .
H5A H -0.2322 0.6896 -0.0998 0.050 Uiso 1 1 calc R . .
H5B H -0.1907 0.7942 -0.1536 0.050 Uiso 1 1 calc R . .
C6 C -0.0568(3) 0.7165(4) -0.06843(18) 0.0382(8) Uani 1 1 d . . .
H6A H -0.0573 0.7970 -0.0359 0.046 Uiso 1 1 calc R . .
H6B H -0.0457 0.6340 -0.0361 0.046 Uiso 1 1 calc R . .
C7 C 0.2713(3) 1.0230(4) 0.00083(18) 0.0385(8) Uani 1 1 d . . .
H7 H 0.2569 1.1163 -0.0130 0.046 Uiso 1 1 calc R . .
C8 C 0.3801(3) 0.9913(4) 0.05334(17) 0.0347(8) Uani 1 1 d . . .
C9 C 0.4144(3) 0.8548(4) 0.07886(18) 0.0360(8) Uani 1 1 d . . .
C10 C 0.5283(3) 0.8337(4) 0.12490(18) 0.0412(9) Uani 1 1 d . . .
H10 H 0.5528 0.7440 0.1415 0.049 Uiso 1 1 calc R . .
C11 C 0.6035(3) 0.9443(4) 0.14556(18) 0.0440(9) Uani 1 1 d . . .
C12 C 0.5693(3) 1.0806(4) 0.12224(19) 0.0469(9) Uani 1 1 d . . .
H12 H 0.6199 1.1552 0.1377 0.056 Uiso 1 1 calc R . .
C13 C 0.4608(3) 1.1020(4) 0.07658(19) 0.0435(9) Uani 1 1 d . . .
H13 H 0.4385 1.1924 0.0599 0.052 Uiso 1 1 calc R . .
C14 C 0.7579(3) 0.7955(5) 0.2116(2) 0.0665(13) Uani 1 1 d . . .
H14A H 0.7175 0.7581 0.2462 0.100 Uiso 1 1 calc R . .
H14B H 0.8392 0.7999 0.2368 0.100 Uiso 1 1 calc R . .
H14C H 0.7453 0.7363 0.1673 0.100 Uiso 1 1 calc R . .
C15 C -0.4699(3) 0.5366(5) -0.1686(2) 0.0678(12) Uani 1 1 d . . .
H15A H -0.4639 0.5501 -0.1151 0.102 Uiso 1 1 calc R . .
H15B H -0.5436 0.4957 -0.1933 0.102 Uiso 1 1 calc R . .
H15C H -0.4629 0.6252 -0.1919 0.102 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 N2 1.909(3) . ?
Cu1 O4 1.915(2) . ?
Cu1 O1 1.980(2) . ?
Cu1 N3 2.115(2) . ?
O1 N1 1.280(4) . ?
O2 N1 1.207(4) . ?
O3 N1 1.231(4) . ?
O4 C9 1.309(4) . ?
O5 C11 1.376(4) . ?
O5 C14 1.404(5) . ?
O6 N5 1.230(4) . ?
O7 N5 1.226(4) . ?
O8 N5 1.242(4) . ?
O9 C15 1.402(4) . ?
O9 H9 0.8200 . ?
N2 C7 1.289(4) . ?
N2 C1 1.462(4) . ?
N3 C6 1.484(4) . ?
N3 C2 1.501(4) . ?
N3 C3 1.492(4) . ?
N4 C5 1.481(4) . ?
N4 C4 1.482(4) . ?
N4 H4A 0.9000 . ?
N4 H4B 0.9000 . ?
C1 C2 1.495(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.514(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4C 0.9700 . ?
C4 H4D 0.9700 . ?
C5 C6 1.503(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.424(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.409(5) . ?
C8 C13 1.419(4) . ?
C9 C10 1.409(4) . ?
C10 C11 1.375(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.397(5) . ?
C12 C13 1.356(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
N2 Cu1 O4 93.56(10) . . ?
N2 Cu1 O1 176.28(10) . . ?
O4 Cu1 O1 88.33(9) . . ?
N2 Cu1 N3 85.24(11) . . ?
O4 Cu1 N3 174.02(10) . . ?
O1 Cu1 N3 92.56(10) . . ?
N1 O1 Cu1 108.8(2) . . ?
C9 O4 Cu1 127.2(2) . . ?
C11 O5 C14 118.1(3) . . ?
C15 O9 H9 109.5 . . ?
O2 N1 O3 122.7(4) . . ?
O2 N1 O1 118.8(4) . . ?
O3 N1 O1 118.5(3) . . ?
C7 N2 C1 119.7(3) . . ?
C7 N2 Cu1 126.0(2) . . ?
C1 N2 Cu1 114.3(2) . . ?
C6 N3 C2 113.3(3) . . ?
C6 N3 C3 106.9(2) . . ?
C2 N3 C3 110.7(3) . . ?
C6 N3 Cu1 109.21(19) . . ?
C2 N3 Cu1 102.17(18) . . ?
C3 N3 Cu1 114.72(19) . . ?
C5 N4 C4 111.8(3) . . ?
C5 N4 H4A 109.3 . . ?
C4 N4 H4A 109.3 . . ?
C5 N4 H4B 109.3 . . ?
C4 N4 H4B 109.3 . . ?
H4A N4 H4B 107.9 . . ?
O7 N5 O6 118.5(3) . . ?
O7 N5 O8 119.6(4) . . ?
O6 N5 O8 122.0(3) . . ?
N2 C1 C2 107.3(3) . . ?
N2 C1 H1A 110.3 . . ?
C2 C1 H1A 110.3 . . ?
N2 C1 H1B 110.2 . . ?
C2 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
N3 C2 C1 110.8(3) . . ?
N3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
N3 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
N3 C3 C4 113.5(3) . . ?
N3 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
N3 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
N4 C4 C3 109.2(2) . . ?
N4 C4 H4C 109.8 . . ?
C3 C4 H4C 109.8 . . ?
N4 C4 H4D 109.8 . . ?
C3 C4 H4D 109.8 . . ?
H4C C4 H4D 108.3 . . ?
N4 C5 C6 110.9(3) . . ?
N4 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
N4 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.0 . . ?
N3 C6 C5 115.0(3) . . ?
N3 C6 H6A 108.5 . . ?
C5 C6 H6A 108.5 . . ?
N3 C6 H6B 108.5 . . ?
C5 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
N2 C7 C8 125.9(3) . . ?
N2 C7 H7 117.0 . . ?
C8 C7 H7 117.0 . . ?
C9 C8 C7 123.3(3) . . ?
C9 C8 C13 118.6(3) . . ?
C7 C8 C13 117.9(3) . . ?
O4 C9 C10 118.0(3) . . ?
O4 C9 C8 123.5(3) . . ?
C10 C9 C8 118.5(3) . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 O5 123.7(4) . . ?
C10 C11 C12 121.1(3) . . ?
O5 C11 C12 115.2(3) . . ?
C13 C12 C11 118.7(3) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C8 122.3(3) . . ?
C12 C13 H13 118.9 . . ?
C8 C13 H13 118.9 . . ?
O5 C14 H14A 109.5 . . ?
O5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O9 C15 H15A 109.5 . . ?
O9 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O9 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.31
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.074
_atom_sites_special_details      
;
The structure was solved using Patterson Methods, followed by a Tangent Expansion (ShelXS). RE = 0.5, Nqual =  -0, Ralpha = 0.087
;
