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

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

data_cl058
_database_code_depnum_ccdc_archive 'CCDC 1566611'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            HL30a
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H16 N2 O3'
_chemical_formula_sum            'C13 H16 N2 O3'
_chemical_formula_weight         248.28

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/a'
_space_group_name_Hall           '-P 2yab'

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

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

_cell_length_a                   7.339(5)
_cell_length_b                   14.815(5)
_cell_length_c                   11.777(5)
_cell_angle_alpha                90.000
_cell_angle_beta                 97.495(5)
_cell_angle_gamma                90.000
_cell_volume                     1269.5(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    3261
_cell_measurement_theta_min      1.74
_cell_measurement_theta_max      25.81

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.124
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.076
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            7264
_diffrn_reflns_av_unetI/netI     0.1192
_diffrn_reflns_av_R_equivalents  0.1123
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.744
_diffrn_reflns_theta_max         28.028
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             2852
_reflns_number_gt                1329
_reflns_threshold_expression     'I > 2σ(I)'

_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0927P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2852
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1440
_refine_ls_R_factor_gt           0.0757
_refine_ls_wR_factor_ref         0.2103
_refine_ls_wR_factor_gt          0.1826
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_restrained_S_all      0.921
_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
C1 C -0.1026(5) 0.3906(2) 0.0140(3) 0.0476(9) Uani 1 1 d . . . . .
H1 H -0.0978 0.4384 -0.0392 0.057 Uiso 1 1 calc R U . . .
C2 C -0.1766(5) 0.3092(2) -0.0260(3) 0.0476(9) Uani 1 1 d . . . . .
H2A H -0.2226 0.3017 -0.1047 0.057 Uiso 1 1 calc R U . . .
C3 C -0.1826(4) 0.2390(2) 0.0500(3) 0.0475(9) Uani 1 1 d . . . . .
H3 H -0.2324 0.1822 0.0246 0.057 Uiso 1 1 calc R U . . .
C4 C -0.1145(4) 0.2527(2) 0.1643(3) 0.0425(8) Uani 1 1 d . . . . .
H4 H -0.1167 0.2056 0.2188 0.051 Uiso 1 1 calc R U . . .
C5 C -0.0431(4) 0.3368(2) 0.1969(3) 0.0398(8) Uani 1 1 d . . . . .
C6 C 0.0328(4) 0.3520(2) 0.3204(3) 0.0418(8) Uani 1 1 d . . . . .
H6A H -0.0640 0.3389 0.3693 0.050 Uiso 1 1 calc R U . . .
H6B H 0.1359 0.3097 0.3421 0.050 Uiso 1 1 calc R U . . .
C7 C 0.1862(4) 0.4706(2) 0.4388(3) 0.0391(8) Uani 1 1 d . . . . .
H7 H 0.2000 0.4276 0.4991 0.047 Uiso 1 1 calc R U . . .
C8 C 0.2628(4) 0.5553(2) 0.4641(3) 0.0409(8) Uani 1 1 d . . . . .
C9 C 0.2502(5) 0.6241(2) 0.3755(3) 0.0451(8) Uani 1 1 d . . . . .
C10 C 0.3429(6) 0.7148(2) 0.3954(4) 0.0568(10) Uani 1 1 d . . . . .
H10A H 0.3123 0.7528 0.3275 0.085 Uiso 1 1 calc R U . . .
H10B H 0.4763 0.7064 0.4100 0.085 Uiso 1 1 calc R U . . .
H10C H 0.3001 0.7441 0.4617 0.085 Uiso 1 1 calc R U . . .
C11 C 0.3627(4) 0.5707(2) 0.5780(3) 0.0444(8) Uani 1 1 d . . . . .
C12 C 0.4346(5) 0.5117(2) 0.7665(3) 0.0477(9) Uani 1 1 d . . . . .
H12A H 0.3933 0.5676 0.8016 0.057 Uiso 1 1 calc R U . . .
H12B H 0.5693 0.5150 0.7664 0.057 Uiso 1 1 calc R U . . .
C13 C 0.3853(5) 0.4304(3) 0.8323(4) 0.0566(10) Uani 1 1 d . . . . .
H13A H 0.2514 0.4268 0.8294 0.085 Uiso 1 1 calc R U . . .
H13B H 0.4417 0.4355 0.9121 0.085 Uiso 1 1 calc R U . . .
H13C H 0.4306 0.3758 0.7982 0.085 Uiso 1 1 calc R U . . .
N1 N -0.0372(4) 0.40562(19) 0.1240(3) 0.0450(7) Uani 1 1 d . . . . .
N2 N 0.0972(3) 0.44378(17) 0.3410(3) 0.0412(7) Uani 1 1 d . . . . .
H2 H 0.0755 0.4833 0.2851 0.049 Uiso 1 1 calc R U . . .
O1 O 0.1621(3) 0.60965(16) 0.2798(2) 0.0533(7) Uani 1 1 d . . . . .
O2 O 0.4536(3) 0.63723(15) 0.6083(2) 0.0513(7) Uani 1 1 d . . . . .
O3 O 0.3421(3) 0.50165(15) 0.6503(2) 0.0465(6) 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
C1 N1 1.340(5) . ?
C1 C2 1.380(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.377(5) . ?
C2 H2A 0.9500 . ?
C3 C4 1.388(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(5) . ?
C4 H4 0.9500 . ?
C5 N1 1.337(4) . ?
C5 C6 1.505(5) . ?
C6 N2 1.449(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.310(4) . ?
C7 C8 1.390(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.453(5) . ?
C8 C11 1.461(5) . ?
C9 O1 1.243(4) . ?
C9 C10 1.510(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O2 1.217(4) . ?
C11 O3 1.353(4) . ?
C12 O3 1.453(4) . ?
C12 C13 1.501(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N2 H2 0.8800 . ?

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
N1 C1 C2 123.5(3) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C3 C2 C1 118.8(4) . . ?
C3 C2 H2A 120.6 . . ?
C1 C2 H2A 120.6 . . ?
C2 C3 C4 118.8(3) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 118.4(3) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
N1 C5 C4 123.4(3) . . ?
N1 C5 C6 117.9(3) . . ?
C4 C5 C6 118.7(3) . . ?
N2 C6 C5 111.9(3) . . ?
N2 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N2 C7 C8 127.1(3) . . ?
N2 C7 H7 116.5 . . ?
C8 C7 H7 116.5 . . ?
C7 C8 C9 119.6(3) . . ?
C7 C8 C11 118.6(3) . . ?
C9 C8 C11 121.8(3) . . ?
O1 C9 C8 120.5(3) . . ?
O1 C9 C10 117.7(3) . . ?
C8 C9 C10 121.9(3) . . ?
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 . . ?
O2 C11 O3 122.0(3) . . ?
O2 C11 C8 125.9(3) . . ?
O3 C11 C8 112.1(3) . . ?
O3 C12 C13 106.8(3) . . ?
O3 C12 H12A 110.4 . . ?
C13 C12 H12A 110.4 . . ?
O3 C12 H12B 110.4 . . ?
C13 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 N1 C1 117.1(3) . . ?
C7 N2 C6 123.1(3) . . ?
C7 N2 H2 118.4 . . ?
C6 N2 H2 118.4 . . ?
C11 O3 C12 116.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.7(5) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C3 C4 C5 N1 0.3(5) . . . . ?
C3 C4 C5 C6 -179.4(3) . . . . ?
N1 C5 C6 N2 1.9(4) . . . . ?
C4 C5 C6 N2 -178.4(3) . . . . ?
N2 C7 C8 C9 -1.1(5) . . . . ?
N2 C7 C8 C11 -177.9(3) . . . . ?
C7 C8 C9 O1 4.4(5) . . . . ?
C11 C8 C9 O1 -179.0(3) . . . . ?
C7 C8 C9 C10 -175.4(3) . . . . ?
C11 C8 C9 C10 1.2(5) . . . . ?
C7 C8 C11 O2 171.3(3) . . . . ?
C9 C8 C11 O2 -5.3(5) . . . . ?
C7 C8 C11 O3 -9.4(4) . . . . ?
C9 C8 C11 O3 173.9(3) . . . . ?
C4 C5 N1 C1 -0.7(5) . . . . ?
C6 C5 N1 C1 178.9(3) . . . . ?
C2 C1 N1 C5 0.9(5) . . . . ?
C8 C7 N2 C6 175.7(3) . . . . ?
C5 C6 N2 C7 -172.7(3) . . . . ?
O2 C11 O3 C12 0.2(4) . . . . ?
C8 C11 O3 C12 -179.1(3) . . . . ?
C13 C12 O3 C11 177.1(3) . . . . ?

_refine_diff_density_max         0.353
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.072

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_cl064
_database_code_depnum_ccdc_archive 'CCDC 1566614'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;
_chemical_name_common            HL30i
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 N2 O3'
_chemical_formula_sum            'C24 H28 N4 O6'
_chemical_formula_weight         468.50

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   25.029(5)
_cell_length_b                   4.211(5)
_cell_length_c                   28.823(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 129.016(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2360(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    5344
_cell_measurement_theta_min      1.70
_cell_measurement_theta_max      28.08

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.111
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.099
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            7104
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         1.702
_diffrn_reflns_theta_max         28.046
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2682
_reflns_number_gt                1680
_reflns_threshold_expression     'I > 2σ(I)'

_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1327P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2682
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_ref         0.2176
_refine_ls_wR_factor_gt          0.1646
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
C1 C 0.74728(15) 0.6758(7) 0.30643(11) 0.0495(7) Uani 1 1 d . . . . .
H1 H 0.7792 0.8033 0.3072 0.059 Uiso 1 1 calc R U . . .
C2 C 0.68297(16) 0.6408(7) 0.25303(10) 0.0534(7) Uani 1 1 d . . . . .
H2 H 0.6704 0.7428 0.2180 0.064 Uiso 1 1 calc R U . . .
C3 C 0.63715(15) 0.4544(8) 0.25149(11) 0.0548(8) Uani 1 1 d . . . . .
H3 H 0.5922 0.4204 0.2150 0.066 Uiso 1 1 calc R U . . .
C4 C 0.65711(13) 0.3150(7) 0.30410(10) 0.0481(7) Uani 1 1 d . . . . .
H4 H 0.6259 0.1876 0.3042 0.058 Uiso 1 1 calc R U . . .
C5 C 0.72326(12) 0.3657(6) 0.35608(9) 0.0376(6) Uani 1 1 d . . . . .
C6 C 0.74886(13) 0.2065(7) 0.41381(9) 0.0421(6) Uani 1 1 d . . . . .
H6A H 0.7087 0.1459 0.4110 0.051 Uiso 1 1 calc R U . . .
H6B H 0.7733 0.0089 0.4185 0.051 Uiso 1 1 calc R U . . .
C7 C 0.86135(12) 0.3892(6) 0.49876(9) 0.0382(6) Uani 1 1 d . . . . .
H7 H 0.8784 0.2595 0.4837 0.046 Uiso 1 1 calc R U . . .
C8 C 0.91035(12) 0.5447(6) 0.55240(9) 0.0379(6) Uani 1 1 d . . . . .
C9 C 0.88896(13) 0.7331(6) 0.58032(9) 0.0403(6) Uani 1 1 d . . . . .
C10 C 0.94021(14) 0.8562(8) 0.64335(11) 0.0516(7) Uani 1 1 d . . . . .
H10A H 0.9156 0.9569 0.6557 0.077 Uiso 1 1 calc R U . . .
H10B H 0.9704 1.0122 0.6450 0.077 Uiso 1 1 calc R U . . .
H10C H 0.9679 0.6792 0.6703 0.077 Uiso 1 1 calc R U . . .
C11 C 0.98306(13) 0.4954(7) 0.58115(10) 0.0415(6) Uani 1 1 d . . . . .
C12 C 1.06216(14) 0.2478(9) 0.57372(11) 0.0554(8) Uani 1 1 d . . . . .
H12A H 1.0864 0.4472 0.5806 0.083 Uiso 1 1 calc R U . . .
H12B H 1.0632 0.1133 0.5465 0.083 Uiso 1 1 calc R U . . .
H12C H 1.0847 0.1371 0.6118 0.083 Uiso 1 1 calc R U . . .
N1 N 0.76866(11) 0.5430(5) 0.35787(8) 0.0427(5) Uani 1 1 d . . . . .
N2 N 0.79461(10) 0.4010(5) 0.46672(8) 0.0378(5) Uani 1 1 d . . . . .
H2A H 0.7767 0.5312 0.4775 0.045 Uiso 1 1 calc R U . . .
O1 O 0.82696(9) 0.7906(5) 0.55323(7) 0.0433(5) Uani 1 1 d . . . . .
O2 O 1.03201(9) 0.5960(5) 0.62934(8) 0.0561(6) Uani 1 1 d . . . . .
O3 O 0.99185(9) 0.3153(5) 0.54756(7) 0.0507(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
C1 N1 1.341(3) . ?
C1 C2 1.365(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.367(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.333(3) . ?
C5 C6 1.512(3) . ?
C6 N2 1.452(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.305(3) . ?
C7 C8 1.391(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.451(3) . ?
C8 C11 1.464(3) . ?
C9 O1 1.245(3) . ?
C9 C10 1.510(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O2 1.211(3) . ?
C11 O3 1.352(3) . ?
C12 O3 1.441(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N2 H2A 0.8800 . ?

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
N1 C1 C2 124.6(3) . . ?
N1 C1 H1 117.7 . . ?
C2 C1 H1 117.7 . . ?
C1 C2 C3 117.9(2) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C2 C3 C4 119.2(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 118.6(3) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
N1 C5 C4 122.6(2) . . ?
N1 C5 C6 116.4(2) . . ?
C4 C5 C6 120.9(2) . . ?
N2 C6 C5 114.4(2) . . ?
N2 C6 H6A 108.7 . . ?
C5 C6 H6A 108.7 . . ?
N2 C6 H6B 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
N2 C7 C8 127.5(2) . . ?
N2 C7 H7 116.2 . . ?
C8 C7 H7 116.3 . . ?
C7 C8 C9 119.9(2) . . ?
C7 C8 C11 118.3(2) . . ?
C9 C8 C11 121.7(2) . . ?
O1 C9 C8 120.5(2) . . ?
O1 C9 C10 117.9(2) . . ?
C8 C9 C10 121.6(2) . . ?
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 . . ?
O2 C11 O3 120.9(2) . . ?
O2 C11 C8 126.8(2) . . ?
O3 C11 C8 112.3(2) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 N1 C1 117.0(2) . . ?
C7 N2 C6 122.2(2) . . ?
C7 N2 H2A 118.9 . . ?
C6 N2 H2A 118.9 . . ?
C11 O3 C12 115.6(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.8(4) . . . . ?
C1 C2 C3 C4 1.4(4) . . . . ?
C2 C3 C4 C5 -1.1(4) . . . . ?
C3 C4 C5 N1 0.1(4) . . . . ?
C3 C4 C5 C6 -176.8(2) . . . . ?
N1 C5 C6 N2 39.4(3) . . . . ?
C4 C5 C6 N2 -143.5(2) . . . . ?
N2 C7 C8 C9 3.6(4) . . . . ?
N2 C7 C8 C11 179.6(2) . . . . ?
C7 C8 C9 O1 -9.2(3) . . . . ?
C11 C8 C9 O1 174.9(2) . . . . ?
C7 C8 C9 C10 168.7(2) . . . . ?
C11 C8 C9 C10 -7.2(4) . . . . ?
C7 C8 C11 O2 -175.1(3) . . . . ?
C9 C8 C11 O2 0.8(4) . . . . ?
C7 C8 C11 O3 4.5(3) . . . . ?
C9 C8 C11 O3 -179.5(2) . . . . ?
C4 C5 N1 C1 0.5(4) . . . . ?
C6 C5 N1 C1 177.6(2) . . . . ?
C2 C1 N1 C5 -0.2(4) . . . . ?
C8 C7 N2 C6 -174.8(2) . . . . ?
C5 C6 N2 C7 -93.1(3) . . . . ?
O2 C11 O3 C12 1.5(4) . . . . ?
C8 C11 O3 C12 -178.2(2) . . . . ?

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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_cl091
_database_code_depnum_ccdc_archive 'CCDC 1566637'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '[CuL30i(SCN)]2'
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H26 Cu2 N6 O6 S2'
_chemical_formula_sum            'C26 H26 Cu2 N6 O6 S2'
_chemical_formula_weight         709.73

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'

_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                   12.3364(8)
_cell_length_b                   13.4022(11)
_cell_length_c                   8.6223(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.437(5)
_cell_angle_gamma                90
_cell_volume                     1413.57(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    4006
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      27.48

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_F_000             724
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.051
_exptl_absorpt_coefficient_mu    1.705
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            8831
_diffrn_reflns_av_unetI/netI     0.1170
_diffrn_reflns_av_R_equivalents  0.0997
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         1.665
_diffrn_reflns_theta_max         28.501
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3338
_reflns_number_gt                1756
_reflns_threshold_expression     'I > 2σ(I)'

_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0624P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3338
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1428
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   0.857
_refine_ls_restrained_S_all      0.857
_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
C1 C 0.1146(4) 0.0838(4) -0.4134(5) 0.0297(11) Uani 1 1 d . . . . .
H1 H 0.0933 0.1363 -0.3537 0.036 Uiso 1 1 calc R U . . .
C2 C 0.0870(4) 0.0868(4) -0.5742(5) 0.0322(11) Uani 1 1 d . . . . .
H2 H 0.0482 0.1403 -0.6224 0.039 Uiso 1 1 calc R U . . .
C3 C 0.1188(4) 0.0080(5) -0.6606(5) 0.0372(12) Uani 1 1 d . . . . .
H3 H 0.1004 0.0078 -0.7687 0.045 Uiso 1 1 calc R U . . .
C4 C 0.1779(4) -0.0708(5) -0.5884(5) 0.0346(12) Uani 1 1 d . . . . .
H4 H 0.1994 -0.1241 -0.6463 0.042 Uiso 1 1 calc R U . . .
C5 C 0.2042(4) -0.0678(4) -0.4257(5) 0.0301(11) Uani 1 1 d . . . . .
C6 C 0.2654(4) -0.1512(4) -0.3344(6) 0.0368(12) Uani 1 1 d . . . . .
H6A H 0.2172 -0.2075 -0.3256 0.044 Uiso 1 1 calc R U . . .
H6B H 0.3260 -0.1733 -0.3870 0.044 Uiso 1 1 calc R U . . .
C7 C 0.3943(4) -0.1503(4) -0.1045(5) 0.0305(11) Uani 1 1 d . . . . .
H7 H 0.4273 -0.2016 -0.1540 0.037 Uiso 1 1 calc R U . . .
C8 C 0.4456(4) -0.1214(4) 0.0452(5) 0.0272(10) Uani 1 1 d . . . . .
C9 C 0.3987(4) -0.0501(4) 0.1379(5) 0.0288(11) Uani 1 1 d . . . . .
C10 C 0.4482(4) -0.0280(4) 0.3032(5) 0.0367(13) Uani 1 1 d . . . . .
H10A H 0.5137 0.0106 0.3018 0.055 Uiso 1 1 calc R U . . .
H10B H 0.4656 -0.0895 0.3579 0.055 Uiso 1 1 calc R U . . .
H10C H 0.3969 0.0091 0.3552 0.055 Uiso 1 1 calc R U . . .
C11 C 0.5530(4) -0.1646(4) 0.0998(5) 0.0294(11) Uani 1 1 d . . . . .
C12 C 0.6772(4) -0.2939(5) 0.0608(7) 0.0442(14) Uani 1 1 d . . . . .
H12A H 0.7298 -0.2477 0.0295 0.066 Uiso 1 1 calc R U . . .
H12B H 0.6803 -0.3551 0.0038 0.066 Uiso 1 1 calc R U . . .
H12C H 0.6933 -0.3069 0.1708 0.066 Uiso 1 1 calc R U . . .
C13 C 0.0430(4) 0.1290(4) -0.0130(5) 0.0304(10) Uani 1 1 d . . . . .
Cu1 Cu 0.22593(5) -0.00082(5) -0.11308(6) 0.03185(19) Uani 1 1 d . . . . .
N1 N 0.1708(3) 0.0081(3) -0.3410(4) 0.0307(9) Uani 1 1 d . . . . .
N2 N 0.3056(3) -0.1122(3) -0.1796(4) 0.0316(10) Uani 1 1 d . . . . .
N13 N 0.1216(4) 0.0942(3) -0.0494(4) 0.0350(10) Uani 1 1 d . . . . .
O1 O 0.3112(3) -0.0029(3) 0.0930(3) 0.0344(8) Uani 1 1 d . . . . .
O2 O 0.6241(3) -0.1283(3) 0.1945(4) 0.0363(8) Uani 1 1 d . . . . .
O3 O 0.5691(3) -0.2516(3) 0.0281(4) 0.0405(9) Uani 1 1 d . . . . .
S13 S -0.06773(11) 0.17811(12) 0.04109(16) 0.0397(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.337(6) . ?
C1 C2 1.385(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.378(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.399(6) . ?
C4 H4 0.9300 . ?
C5 N1 1.347(6) . ?
C5 C6 1.511(7) . ?
C6 N2 1.459(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N2 1.302(6) . ?
C7 C8 1.416(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.417(7) . ?
C8 C11 1.466(6) . ?
C9 O1 1.267(5) . ?
C9 C10 1.506(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 O2 1.220(6) . ?
C11 O3 1.347(6) . ?
C12 O3 1.442(6) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N13 1.155(6) . ?
C13 S13 1.638(5) . ?
Cu1 N2 1.916(4) . ?
Cu1 N13 1.940(4) . ?
Cu1 O1 1.945(3) . ?
Cu1 N1 1.998(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
N1 C1 C2 122.3(5) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C3 C2 C1 118.0(5) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 120.8(4) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 118.0(5) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
N1 C5 C4 121.2(5) . . ?
N1 C5 C6 116.3(4) . . ?
C4 C5 C6 122.4(5) . . ?
N2 C6 C5 107.4(4) . . ?
N2 C6 H6A 110.2 . . ?
C5 C6 H6A 110.2 . . ?
N2 C6 H6B 110.2 . . ?
C5 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
N2 C7 C8 126.4(5) . . ?
N2 C7 H7 116.8 . . ?
C8 C7 H7 116.8 . . ?
C7 C8 C9 122.1(4) . . ?
C7 C8 C11 117.6(4) . . ?
C9 C8 C11 120.2(4) . . ?
O1 C9 C8 123.9(4) . . ?
O1 C9 C10 114.6(4) . . ?
C8 C9 C10 121.4(4) . . ?
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 . . ?
O2 C11 O3 121.1(4) . . ?
O2 C11 C8 126.8(5) . . ?
O3 C11 C8 112.1(4) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N13 C13 S13 179.2(4) . . ?
N2 Cu1 N13 168.92(19) . . ?
N2 Cu1 O1 91.39(15) . . ?
N13 Cu1 O1 92.94(16) . . ?
N2 Cu1 N1 82.80(17) . . ?
N13 Cu1 N1 94.90(17) . . ?
O1 Cu1 N1 167.04(14) . . ?
C1 N1 C5 119.8(4) . . ?
C1 N1 Cu1 126.5(3) . . ?
C5 N1 Cu1 113.5(3) . . ?
C7 N2 C6 118.6(4) . . ?
C7 N2 Cu1 126.0(3) . . ?
C6 N2 Cu1 115.2(3) . . ?
C13 N13 Cu1 162.3(5) . . ?
C9 O1 Cu1 128.7(3) . . ?
C11 O3 C12 116.0(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
N1 C1 C2 C3 0.3(7) . . . . ?
C1 C2 C3 C4 -0.9(7) . . . . ?
C2 C3 C4 C5 -0.1(7) . . . . ?
C3 C4 C5 N1 1.7(7) . . . . ?
C3 C4 C5 C6 178.1(5) . . . . ?
N1 C5 C6 N2 -19.3(6) . . . . ?
C4 C5 C6 N2 164.1(5) . . . . ?
N2 C7 C8 C9 5.3(8) . . . . ?
N2 C7 C8 C11 -172.0(5) . . . . ?
C7 C8 C9 O1 -3.7(8) . . . . ?
C11 C8 C9 O1 173.5(5) . . . . ?
C7 C8 C9 C10 173.6(5) . . . . ?
C11 C8 C9 C10 -9.3(7) . . . . ?
C7 C8 C11 O2 154.3(5) . . . . ?
C9 C8 C11 O2 -23.0(7) . . . . ?
C7 C8 C11 O3 -23.3(6) . . . . ?
C9 C8 C11 O3 159.4(4) . . . . ?
C2 C1 N1 C5 1.2(7) . . . . ?
C2 C1 N1 Cu1 174.9(3) . . . . ?
C4 C5 N1 C1 -2.2(7) . . . . ?
C6 C5 N1 C1 -178.9(4) . . . . ?
C4 C5 N1 Cu1 -176.7(4) . . . . ?
C6 C5 N1 Cu1 6.6(5) . . . . ?
C8 C7 N2 C6 179.3(5) . . . . ?
C8 C7 N2 Cu1 4.3(8) . . . . ?
C5 C6 N2 C7 -151.6(5) . . . . ?
C5 C6 N2 Cu1 23.9(5) . . . . ?
C8 C9 O1 Cu1 -7.4(7) . . . . ?
C10 C9 O1 Cu1 175.2(3) . . . . ?
O2 C11 O3 C12 -4.7(7) . . . . ?
C8 C11 O3 C12 173.0(4) . . . . ?

_refine_diff_density_max         0.615
_refine_diff_density_min         -0.661
_refine_diff_density_rms         0.113

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_cl107
_database_code_depnum_ccdc_archive 'CCDC 1566612'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;
_chemical_name_common            HL30d
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H13 N3 O2'
_chemical_formula_sum            'C12 H13 N3 O2'
_chemical_formula_weight         231.25

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

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

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

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

_cell_length_a                   6.0280(4)
_cell_length_b                   9.2207(6)
_cell_length_c                   11.3737(7)
_cell_angle_alpha                74.653(5)
_cell_angle_beta                 75.243(5)
_cell_angle_gamma                87.728(5)
_cell_volume                     589.26(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    5045
_cell_measurement_theta_min      1.92
_cell_measurement_theta_max      28.42

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             244
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.266
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.137
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            6744
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.919
_diffrn_reflns_theta_max         28.395
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             2762
_reflns_number_gt                2075
_reflns_threshold_expression     'I > 2σ(I)'

_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0680P)²+0.0156P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2762
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1172
_refine_ls_wR_factor_gt          0.1119
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
C1 C 0.0623(3) -0.07400(17) 0.32595(16) 0.0396(4) Uani 1 1 d . . . . .
H1 H -0.0498 -0.1350 0.3147 0.047 Uiso 1 1 calc R U . . .
C2 C 0.2599(3) -0.14038(17) 0.34986(15) 0.0373(3) Uani 1 1 d . . . . .
H2 H 0.2824 -0.2445 0.3565 0.045 Uiso 1 1 calc R U . . .
C3 C 0.4239(3) -0.05171(19) 0.36389(16) 0.0406(4) Uani 1 1 d . . . . .
H3 H 0.5627 -0.0937 0.3807 0.049 Uiso 1 1 calc R U . . .
C4 C 0.3847(2) 0.09953(17) 0.35321(14) 0.0338(3) Uani 1 1 d . . . . .
H4 H 0.4973 0.1633 0.3608 0.041 Uiso 1 1 calc R U . . .
C5 C 0.1791(2) 0.15637(15) 0.33133(11) 0.0237(3) Uani 1 1 d . . . . .
C6 C 0.1148(2) 0.31850(15) 0.32060(12) 0.0261(3) Uani 1 1 d . . . . .
H6A H 0.0660 0.3584 0.2416 0.031 Uiso 1 1 calc R U . . .
H6B H -0.0182 0.3223 0.3917 0.031 Uiso 1 1 calc R U . . .
C7 C 0.4528(2) 0.48210(14) 0.21693(12) 0.0252(3) Uani 1 1 d . . . . .
H7 H 0.4290 0.4719 0.1401 0.030 Uiso 1 1 calc R U . . .
C8 C 0.6446(2) 0.56504(14) 0.20853(12) 0.0248(3) Uani 1 1 d . . . . .
C12 C 0.6968(2) 0.58406(14) 0.31868(12) 0.0236(3) Uani 1 1 d . . . . .
C9 C 0.7963(2) 0.62970(15) 0.08449(12) 0.0267(3) Uani 1 1 d . . . . .
C10 C 1.1410(3) 0.77063(17) -0.02709(13) 0.0349(3) Uani 1 1 d . . . . .
H10A H 1.0631 0.8261 -0.0917 0.042 Uiso 1 1 calc R U . . .
H10B H 1.2296 0.6894 -0.0578 0.042 Uiso 1 1 calc R U . . .
C11 C 1.2976(3) 0.87524(18) -0.00256(15) 0.0385(3) Uani 1 1 d . . . . .
H11A H 1.2097 0.9586 0.0225 0.058 Uiso 1 1 calc R U . . .
H11B H 1.4192 0.9150 -0.0794 0.058 Uiso 1 1 calc R U . . .
H11C H 1.3663 0.8205 0.0652 0.058 Uiso 1 1 calc R U . . .
N1 N 0.01793(19) 0.07106(14) 0.31755(12) 0.0333(3) Uani 1 1 d . . . . .
N2 N 0.30001(18) 0.41590(12) 0.32098(10) 0.0268(2) Uani 1 1 d . . . . .
H2A H 0.3095 0.4306 0.3929 0.032 Uiso 1 1 calc R U . . .
N3 N 0.7316(2) 0.59551(14) 0.41019(11) 0.0310(3) Uani 1 1 d . . . . .
O1 O 0.76777(17) 0.61523(12) -0.01386(9) 0.0363(3) Uani 1 1 d . . . . .
O2 O 0.97292(16) 0.70758(11) 0.09161(8) 0.0292(2) 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
C1 N1 1.337(2) . ?
C1 C2 1.373(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.373(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3812(18) . ?
C4 H4 0.9500 . ?
C5 N1 1.3383(16) . ?
C5 C6 1.5106(19) . ?
C6 N2 1.4621(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.3147(17) . ?
C7 C8 1.3802(17) . ?
C7 H7 0.9500 . ?
C8 C12 1.4216(16) . ?
C8 C9 1.4571(18) . ?
C12 N3 1.1444(17) . ?
C9 O1 1.2154(15) . ?
C9 O2 1.3384(15) . ?
C10 O2 1.4566(16) . ?
C10 C11 1.4994(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N2 H2A 0.8800 . ?

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
N1 C1 C2 124.11(14) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C3 C2 C1 117.99(14) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 119.18(13) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 118.97(13) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 122.39(13) . . ?
N1 C5 C6 113.80(11) . . ?
C4 C5 C6 123.81(12) . . ?
N2 C6 C5 114.01(10) . . ?
N2 C6 H6A 108.8 . . ?
C5 C6 H6A 108.8 . . ?
N2 C6 H6B 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.6 . . ?
N2 C7 C8 126.31(11) . . ?
N2 C7 H7 116.8 . . ?
C8 C7 H7 116.8 . . ?
C7 C8 C12 120.86(11) . . ?
C7 C8 C9 118.66(11) . . ?
C12 C8 C9 120.46(11) . . ?
N3 C12 C8 177.24(13) . . ?
O1 C9 O2 123.69(12) . . ?
O1 C9 C8 124.65(11) . . ?
O2 C9 C8 111.66(10) . . ?
O2 C10 C11 107.23(11) . . ?
O2 C10 H10A 110.3 . . ?
C11 C10 H10A 110.3 . . ?
O2 C10 H10B 110.3 . . ?
C11 C10 H10B 110.3 . . ?
H10A C10 H10B 108.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 N1 C5 117.34(12) . . ?
C7 N2 C6 121.89(11) . . ?
C7 N2 H2A 119.1 . . ?
C6 N2 H2A 119.1 . . ?
C9 O2 C10 115.88(10) . . ?

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
N1 C1 C2 C3 -1.2(2) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C2 C3 C4 C5 1.3(2) . . . . ?
C3 C4 C5 N1 -1.4(2) . . . . ?
C3 C4 C5 C6 178.70(14) . . . . ?
N1 C5 C6 N2 -173.30(11) . . . . ?
C4 C5 C6 N2 6.65(18) . . . . ?
N2 C7 C8 C12 1.2(2) . . . . ?
N2 C7 C8 C9 179.63(12) . . . . ?
C7 C8 C9 O1 -0.6(2) . . . . ?
C12 C8 C9 O1 177.85(13) . . . . ?
C7 C8 C9 O2 179.53(12) . . . . ?
C12 C8 C9 O2 -2.05(17) . . . . ?
C2 C1 N1 C5 1.2(2) . . . . ?
C4 C5 N1 C1 0.1(2) . . . . ?
C6 C5 N1 C1 -179.95(13) . . . . ?
C8 C7 N2 C6 -173.99(12) . . . . ?
C5 C6 N2 C7 86.96(15) . . . . ?
O1 C9 O2 C10 -2.8(2) . . . . ?
C8 C9 O2 C10 177.09(11) . . . . ?
C11 C10 O2 C9 169.83(12) . . . . ?

_refine_diff_density_max         0.280
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_cl100
_database_code_depnum_ccdc_archive 'CCDC 1566623'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '[CuL30aCl]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H30 Cl2 Cu2 N4 O6'
_chemical_formula_sum            'C26 H30 Cl2 Cu2 N4 O6'
_chemical_formula_weight         692.54

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                   7.3859(5)
_cell_length_b                   9.1298(7)
_cell_length_c                   10.3252(7)
_cell_angle_alpha                94.110(6)
_cell_angle_beta                 96.016(6)
_cell_angle_gamma                105.895(6)
_cell_volume                     662.26(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    5999
_cell_measurement_theta_min      2.00
_cell_measurement_theta_max      28.40

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.736
_exptl_crystal_F_000             354
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.093
_exptl_absorpt_coefficient_mu    1.858
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            6277
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_av_R_equivalents  0.0820
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.994
_diffrn_reflns_theta_max         28.497
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             3054
_reflns_number_gt                2501
_reflns_threshold_expression     'I > 2σ(I)'


_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1157P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3054
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1742
_refine_ls_wR_factor_gt          0.1635
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
C1 C 0.4204(6) 0.2756(5) 0.6644(4) 0.0314(8) Uani 1 1 d . . . . .
H1 H 0.4765 0.2086 0.7096 0.038 Uiso 1 1 calc R U . . .
C2 C 0.4546(6) 0.4243(5) 0.7186(4) 0.0336(9) Uani 1 1 d . . . . .
H2 H 0.5319 0.4589 0.8005 0.040 Uiso 1 1 calc R U . . .
C3 C 0.3749(6) 0.5228(5) 0.6523(4) 0.0342(9) Uani 1 1 d . . . . .
H3 H 0.3981 0.6262 0.6877 0.041 Uiso 1 1 calc R U . . .
C4 C 0.2614(6) 0.4692(5) 0.5344(4) 0.0323(8) Uani 1 1 d . . . . .
H4 H 0.2049 0.5350 0.4878 0.039 Uiso 1 1 calc R U . . .
C5 C 0.2309(6) 0.3179(5) 0.4848(4) 0.0289(8) Uani 1 1 d . . . . .
C6 C 0.1101(6) 0.2519(5) 0.3563(4) 0.0311(8) Uani 1 1 d . . . . .
H6A H -0.0205 0.2593 0.3601 0.037 Uiso 1 1 calc R U . . .
H6B H 0.1627 0.3109 0.2853 0.037 Uiso 1 1 calc R U . . .
C7 C -0.0068(6) 0.0159(5) 0.2256(4) 0.0306(8) Uani 1 1 d . . . . .
H7 H -0.0795 0.0702 0.1778 0.037 Uiso 1 1 calc R U . . .
C8 C -0.0326(6) -0.1394(5) 0.1767(4) 0.0301(8) Uani 1 1 d . . . . .
C9 C 0.0659(6) -0.2315(5) 0.2404(4) 0.0289(8) Uani 1 1 d . . . . .
C10 C 0.0436(6) -0.3947(5) 0.1887(4) 0.0348(9) Uani 1 1 d . . . . .
H10A H 0.1175 -0.4404 0.2498 0.052 Uiso 1 1 calc R U . . .
H10B H 0.0893 -0.3969 0.1031 0.052 Uiso 1 1 calc R U . . .
H10C H -0.0907 -0.4530 0.1797 0.052 Uiso 1 1 calc R U . . .
C11 C -0.1691(6) -0.2012(5) 0.0583(4) 0.0324(8) Uani 1 1 d . . . . .
C12 C -0.4247(6) -0.1548(5) -0.0801(4) 0.0359(9) Uani 1 1 d . . . . .
H12A H -0.3804 -0.2133 -0.1484 0.043 Uiso 1 1 calc R U . . .
H12B H -0.4476 -0.0633 -0.1171 0.043 Uiso 1 1 calc R U . . .
C13 C -0.6071(7) -0.2528(6) -0.0425(4) 0.0396(10) Uani 1 1 d . . . . .
H13A H -0.5893 -0.3502 -0.0181 0.059 Uiso 1 1 calc R U . . .
H13B H -0.7076 -0.2726 -0.1169 0.059 Uiso 1 1 calc R U . . .
H13C H -0.6432 -0.1995 0.0321 0.059 Uiso 1 1 calc R U . . .
N1 N 0.3092(5) 0.2218(4) 0.5486(3) 0.0291(7) Uani 1 1 d . . . . .
N2 N 0.1057(5) 0.0915(4) 0.3286(3) 0.0308(7) Uani 1 1 d . . . . .
O1 O 0.1791(4) -0.1851(4) 0.3477(3) 0.0348(6) Uani 1 1 d . . . . .
O2 O -0.1906(5) -0.3199(4) -0.0097(3) 0.0440(8) Uani 1 1 d . . . . .
O3 O -0.2796(4) -0.1069(4) 0.0322(3) 0.0360(7) Uani 1 1 d . . . . .
Cl1 Cl 0.38040(14) -0.09275(12) 0.62234(9) 0.0316(2) Uani 1 1 d . . . . .
Cu1 Cu 0.25790(7) 0.01183(6) 0.45234(4) 0.0292(2) 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
C1 N1 1.354(5) . ?
C1 C2 1.376(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.385(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(6) . ?
C4 H4 0.9500 . ?
C5 N1 1.348(5) . ?
C5 C6 1.504(6) . ?
C6 N2 1.463(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.302(5) . ?
C7 C8 1.426(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.408(5) . ?
C8 C11 1.470(6) . ?
C9 O1 1.284(5) . ?
C9 C10 1.504(6) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O2 1.211(6) . ?
C11 O3 1.360(5) . ?
C12 O3 1.448(5) . ?
C12 C13 1.505(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N1 Cu1 2.015(4) . ?
N2 Cu1 1.924(3) . ?
O1 Cu1 1.938(3) . ?
Cl1 Cu1 2.2785(9) . ?

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
N1 C1 C2 122.0(4) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C1 C2 C3 119.2(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 119.3(4) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 119.0(4) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.9(4) . . ?
N1 C5 C6 116.2(4) . . ?
C4 C5 C6 122.0(3) . . ?
N2 C6 C5 109.7(3) . . ?
N2 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 127.0(4) . . ?
N2 C7 H7 116.5 . . ?
C8 C7 H7 116.5 . . ?
C9 C8 C7 121.5(4) . . ?
C9 C8 C11 121.1(4) . . ?
C7 C8 C11 117.4(4) . . ?
O1 C9 C8 123.3(4) . . ?
O1 C9 C10 114.5(4) . . ?
C8 C9 C10 122.2(4) . . ?
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 . . ?
O2 C11 O3 121.5(4) . . ?
O2 C11 C8 127.7(4) . . ?
O3 C11 C8 110.8(4) . . ?
O3 C12 C13 110.9(3) . . ?
O3 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 N1 C1 118.6(4) . . ?
C5 N1 Cu1 114.7(3) . . ?
C1 N1 Cu1 126.6(3) . . ?
C7 N2 C6 116.4(3) . . ?
C7 N2 Cu1 126.8(3) . . ?
C6 N2 Cu1 116.7(3) . . ?
C9 O1 Cu1 130.9(3) . . ?
C11 O3 C12 117.2(4) . . ?
N2 Cu1 O1 90.36(14) . . ?
N2 Cu1 N1 82.52(14) . . ?
O1 Cu1 N1 172.41(12) . . ?
N2 Cu1 Cl1 167.34(11) . . ?
O1 Cu1 Cl1 90.67(9) . . ?
N1 Cu1 Cl1 95.70(9) . . ?

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
N1 C1 C2 C3 -0.8(6) . . . . ?
C1 C2 C3 C4 0.8(6) . . . . ?
C2 C3 C4 C5 -0.4(6) . . . . ?
C3 C4 C5 N1 -0.1(6) . . . . ?
C3 C4 C5 C6 -179.5(4) . . . . ?
N1 C5 C6 N2 -0.2(5) . . . . ?
C4 C5 C6 N2 179.3(3) . . . . ?
N2 C7 C8 C9 0.8(6) . . . . ?
N2 C7 C8 C11 179.6(4) . . . . ?
C7 C8 C9 O1 2.5(6) . . . . ?
C11 C8 C9 O1 -176.3(4) . . . . ?
C7 C8 C9 C10 -178.7(4) . . . . ?
C11 C8 C9 C10 2.5(6) . . . . ?
C9 C8 C11 O2 -13.5(7) . . . . ?
C7 C8 C11 O2 167.7(4) . . . . ?
C9 C8 C11 O3 165.1(4) . . . . ?
C7 C8 C11 O3 -13.7(5) . . . . ?
C4 C5 N1 C1 0.1(6) . . . . ?
C6 C5 N1 C1 179.5(3) . . . . ?
C4 C5 N1 Cu1 -176.4(3) . . . . ?
C6 C5 N1 Cu1 3.1(4) . . . . ?
C2 C1 N1 C5 0.3(6) . . . . ?
C2 C1 N1 Cu1 176.3(3) . . . . ?
C8 C7 N2 C6 178.4(4) . . . . ?
C8 C7 N2 Cu1 -4.5(6) . . . . ?
C5 C6 N2 C7 174.4(3) . . . . ?
C5 C6 N2 Cu1 -3.0(4) . . . . ?
C8 C9 O1 Cu1 -1.8(6) . . . . ?
C10 C9 O1 Cu1 179.3(3) . . . . ?
O2 C11 O3 C12 0.2(6) . . . . ?
C8 C11 O3 C12 -178.5(4) . . . . ?
C13 C12 O3 C11 88.7(4) . . . . ?

_refine_diff_density_max         1.343
_refine_diff_density_min         -1.727
_refine_diff_density_rms         0.147

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_cl094
_database_code_depnum_ccdc_archive 'CCDC 1566627'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '[CuL30iCl]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H26 Cl2 Cu2 N4 O6'
_chemical_formula_sum            'C24 H26 Cl2 Cu2 N4 O6'
_chemical_formula_weight         664.46

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                   7.5941(5)
_cell_length_b                   9.0685(6)
_cell_length_c                   10.0399(6)
_cell_angle_alpha                90.393(5)
_cell_angle_beta                 96.377(5)
_cell_angle_gamma                110.150(5)
_cell_volume                     644.33(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    5836
_cell_measurement_theta_min      2.05
_cell_measurement_theta_max      28.44

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_F_000             338
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.082
_exptl_absorpt_coefficient_mu    1.906
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            7133
_diffrn_reflns_av_unetI/netI     0.0715
_diffrn_reflns_av_R_equivalents  0.0786
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.043
_diffrn_reflns_theta_max         28.488
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             3031
_reflns_number_gt                2347
_reflns_threshold_expression     'I > 2σ(I)'


_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0725P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3031
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1218
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_restrained_S_all      0.942
_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
C1 C 0.5781(5) 0.2359(4) -0.1640(3) 0.0359(7) Uani 1 1 d . . . . .
H1 H 0.5201 0.3032 -0.2074 0.043 Uiso 1 1 calc R U . . .
C2 C 0.5500(5) 0.0918(4) -0.2243(3) 0.0384(7) Uani 1 1 d . . . . .
H2 H 0.4742 0.0601 -0.3084 0.046 Uiso 1 1 calc R U . . .
C3 C 0.6339(5) -0.0069(4) -0.1607(3) 0.0381(7) Uani 1 1 d . . . . .
H3 H 0.6169 -0.1065 -0.2015 0.046 Uiso 1 1 calc R U . . .
C4 C 0.7421(5) 0.0404(4) -0.0381(3) 0.0373(7) Uani 1 1 d . . . . .
H4 H 0.7995 -0.0261 0.0073 0.045 Uiso 1 1 calc R U . . .
C5 C 0.7655(5) 0.1881(4) 0.0178(3) 0.0323(6) Uani 1 1 d . . . . .
C6 C 0.8770(5) 0.2452(4) 0.1522(3) 0.0378(7) Uani 1 1 d . . . . .
H6A H 0.8147 0.1773 0.2225 0.045 Uiso 1 1 calc R U . . .
H6B H 1.0055 0.2407 0.1528 0.045 Uiso 1 1 calc R U . . .
C7 C 1.0105(5) 0.4852(4) 0.2802(3) 0.0344(7) Uani 1 1 d . . . . .
H7 H 1.0899 0.4342 0.3235 0.041 Uiso 1 1 calc R U . . .
C8 C 1.0355(5) 0.6387(4) 0.3310(3) 0.0358(7) Uani 1 1 d . . . . .
C9 C 0.9247(5) 0.7248(4) 0.2750(3) 0.0382(7) Uani 1 1 d . . . . .
C10 C 0.9385(6) 0.8828(4) 0.3328(4) 0.0477(9) Uani 1 1 d . . . . .
H10A H 0.8565 0.9252 0.2750 0.072 Uiso 1 1 calc R U . . .
H10B H 1.0695 0.9551 0.3383 0.072 Uiso 1 1 calc R U . . .
H10C H 0.8986 0.8709 0.4229 0.072 Uiso 1 1 calc R U . . .
C11 C 1.1853(5) 0.7057(4) 0.4432(3) 0.0387(7) Uani 1 1 d . . . . .
C12 C 1.4557(7) 0.6838(5) 0.5659(4) 0.0558(11) Uani 1 1 d . . . . .
H12A H 1.5355 0.7911 0.5494 0.084 Uiso 1 1 calc R U . . .
H12B H 1.5321 0.6157 0.5720 0.084 Uiso 1 1 calc R U . . .
H12C H 1.4020 0.6839 0.6502 0.084 Uiso 1 1 calc R U . . .
N1 N 0.6853(4) 0.2845(3) -0.0451(3) 0.0317(5) Uani 1 1 d . . . . .
N2 N 0.8890(4) 0.4083(3) 0.1799(3) 0.0336(6) Uani 1 1 d . . . . .
O1 O 0.8055(4) 0.6778(3) 0.1699(2) 0.0404(5) Uani 1 1 d . . . . .
O2 O 1.2063(4) 0.8194(3) 0.5156(3) 0.0499(7) Uani 1 1 d . . . . .
O3 O 1.3055(4) 0.6260(3) 0.4575(2) 0.0435(6) Uani 1 1 d . . . . .
Cl1 Cl 0.63354(12) 0.61022(9) -0.11869(8) 0.0359(2) Uani 1 1 d . . . . .
Cu1 Cu 0.73464(6) 0.48844(4) 0.05665(4) 0.03314(15) 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
C1 N1 1.346(4) . ?
C1 C2 1.375(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.387(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(4) . ?
C4 H4 0.9500 . ?
C5 N1 1.350(4) . ?
C5 C6 1.497(4) . ?
C6 N2 1.472(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.302(4) . ?
C7 C8 1.421(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.410(5) . ?
C8 C11 1.470(5) . ?
C9 O1 1.277(4) . ?
C9 C10 1.508(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O2 1.212(4) . ?
C11 O3 1.343(4) . ?
C12 O3 1.437(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N1 Cu1 2.004(3) . ?
N2 Cu1 1.926(3) . ?
O1 Cu1 1.932(2) . ?
Cl1 Cu1 2.2845(8) . ?

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
N1 C1 C2 121.9(3) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C1 C2 C3 119.1(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 118.5(3) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 121.7(3) . . ?
N1 C5 C6 117.0(3) . . ?
C4 C5 C6 121.3(3) . . ?
N2 C6 C5 109.0(3) . . ?
N2 C6 H6A 109.9 . . ?
C5 C6 H6A 109.9 . . ?
N2 C6 H6B 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
N2 C7 C8 126.0(3) . . ?
N2 C7 H7 117.0 . . ?
C8 C7 H7 117.0 . . ?
C9 C8 C7 121.8(3) . . ?
C9 C8 C11 121.2(3) . . ?
C7 C8 C11 117.1(3) . . ?
O1 C9 C8 123.4(3) . . ?
O1 C9 C10 113.7(3) . . ?
C8 C9 C10 122.9(3) . . ?
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 . . ?
O2 C11 O3 121.6(3) . . ?
O2 C11 C8 126.8(3) . . ?
O3 C11 C8 111.6(3) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 N1 C5 119.1(3) . . ?
C1 N1 Cu1 126.5(2) . . ?
C5 N1 Cu1 114.4(2) . . ?
C7 N2 C6 116.5(3) . . ?
C7 N2 Cu1 127.1(2) . . ?
C6 N2 Cu1 116.3(2) . . ?
C9 O1 Cu1 130.8(2) . . ?
C11 O3 C12 115.0(3) . . ?
N2 Cu1 O1 90.01(10) . . ?
N2 Cu1 N1 82.71(10) . . ?
O1 Cu1 N1 172.67(10) . . ?
N2 Cu1 Cl1 162.75(9) . . ?
O1 Cu1 Cl1 90.71(7) . . ?
N1 Cu1 Cl1 96.00(8) . . ?

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
N1 C1 C2 C3 0.3(5) . . . . ?
C1 C2 C3 C4 0.6(5) . . . . ?
C2 C3 C4 C5 -0.7(5) . . . . ?
C3 C4 C5 N1 0.0(5) . . . . ?
C3 C4 C5 C6 178.4(3) . . . . ?
N1 C5 C6 N2 -5.7(4) . . . . ?
C4 C5 C6 N2 175.8(3) . . . . ?
N2 C7 C8 C9 0.4(6) . . . . ?
N2 C7 C8 C11 -178.3(3) . . . . ?
C7 C8 C9 O1 -5.4(6) . . . . ?
C11 C8 C9 O1 173.2(3) . . . . ?
C7 C8 C9 C10 175.5(3) . . . . ?
C11 C8 C9 C10 -5.9(5) . . . . ?
C9 C8 C11 O2 15.9(6) . . . . ?
C7 C8 C11 O2 -165.4(4) . . . . ?
C9 C8 C11 O3 -163.1(3) . . . . ?
C7 C8 C11 O3 15.6(4) . . . . ?
C2 C1 N1 C5 -1.0(5) . . . . ?
C2 C1 N1 Cu1 -178.7(3) . . . . ?
C4 C5 N1 C1 0.8(5) . . . . ?
C6 C5 N1 C1 -177.7(3) . . . . ?
C4 C5 N1 Cu1 178.8(3) . . . . ?
C6 C5 N1 Cu1 0.3(4) . . . . ?
C8 C7 N2 C6 -174.9(3) . . . . ?
C8 C7 N2 Cu1 9.4(5) . . . . ?
C5 C6 N2 C7 -167.3(3) . . . . ?
C5 C6 N2 Cu1 8.9(4) . . . . ?
C8 C9 O1 Cu1 0.2(5) . . . . ?
C10 C9 O1 Cu1 179.4(3) . . . . ?
O2 C11 O3 C12 1.4(5) . . . . ?
C8 C11 O3 C12 -179.6(3) . . . . ?

_refine_diff_density_max         0.801
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.106

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_cl077
_database_code_depnum_ccdc_archive 'CCDC 1566624'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            '[CuL30bCl]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H26 Cl2 Cu2 N4 O4'
_chemical_formula_sum            'C24 H26 Cl2 Cu2 N4 O4'
_chemical_formula_weight         632.46

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                   7.6352(5)
_cell_length_b                   9.0924(6)
_cell_length_c                   9.5031(6)
_cell_angle_alpha                91.652(5)
_cell_angle_beta                 98.150(5)
_cell_angle_gamma                107.858(5)
_cell_volume                     619.77(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    5807
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      28.08

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_F_000             322
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.124
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.043
_exptl_absorpt_coefficient_mu    1.971
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            6376
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_av_R_equivalents  0.0792
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.171
_diffrn_reflns_theta_max         28.048
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             2769
_reflns_number_gt                2197
_reflns_threshold_expression     'I > 2σ(I)'


_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0720P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2769
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1175
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_restrained_S_all      0.962
_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
C1 C 0.5406(5) 0.2199(4) 0.8174(4) 0.0243(7) Uani 1 1 d . . . . .
H1 H 0.4767 0.2867 0.7758 0.029 Uiso 1 1 calc R U . . .
C2 C 0.5019(5) 0.0737(4) 0.7530(4) 0.0260(7) Uani 1 1 d . . . . .
H2 H 0.4138 0.0401 0.6680 0.031 Uiso 1 1 calc R U . . .
C3 C 0.5938(5) -0.0230(4) 0.8146(4) 0.0279(7) Uani 1 1 d . . . . .
H3 H 0.5693 -0.1247 0.7724 0.034 Uiso 1 1 calc R U . . .
C4 C 0.7226(5) 0.0285(4) 0.9386(4) 0.0258(7) Uani 1 1 d . . . . .
H4 H 0.7866 -0.0370 0.9823 0.031 Uiso 1 1 calc R U . . .
C5 C 0.7554(5) 0.1778(4) 0.9972(3) 0.0218(6) Uani 1 1 d . . . . .
C6 C 0.8912(5) 0.2413(4) 1.1309(4) 0.0242(7) Uani 1 1 d . . . . .
H6A H 0.8499 0.1789 1.2108 0.029 Uiso 1 1 calc R U . . .
H6B H 1.0154 0.2353 1.1184 0.029 Uiso 1 1 calc R U . . .
C7 C 1.0241(5) 0.4775(4) 1.2740(3) 0.0218(6) Uani 1 1 d . . . . .
H7 H 1.1007 0.4231 1.3210 0.026 Uiso 1 1 calc R U . . .
C8 C 1.0529(5) 0.6299(4) 1.3305(3) 0.0227(7) Uani 1 1 d . . . . .
C9 C 0.9500(5) 0.7223(4) 1.2669(4) 0.0225(6) Uani 1 1 d . . . . .
C10 C 0.9703(6) 0.8824(4) 1.3273(4) 0.0318(8) Uani 1 1 d . . . . .
H10A H 0.9129 0.9359 1.2554 0.048 Uiso 1 1 calc R U . . .
H10B H 1.1028 0.9407 1.3544 0.048 Uiso 1 1 calc R U . . .
H10C H 0.9083 0.8750 1.4116 0.048 Uiso 1 1 calc R U . . .
C11 C 1.1936(5) 0.6876(4) 1.4598(4) 0.0258(7) Uani 1 1 d . . . . .
C12 C 1.3348(6) 0.6033(5) 1.5005(4) 0.0327(8) Uani 1 1 d . . . . .
H12A H 1.4430 0.6725 1.5640 0.049 Uiso 1 1 calc R U . . .
H12B H 1.3749 0.5715 1.4143 0.049 Uiso 1 1 calc R U . . .
H12C H 1.2777 0.5114 1.5495 0.049 Uiso 1 1 calc R U . . .
N1 N 0.6661(4) 0.2724(3) 0.9375(3) 0.0205(5) Uani 1 1 d . . . . .
N2 N 0.9035(4) 0.4038(3) 1.1641(3) 0.0212(6) Uani 1 1 d . . . . .
O1 O 0.8325(3) 0.6789(3) 1.1513(3) 0.0253(5) Uani 1 1 d . . . . .
O2 O 1.2026(4) 0.8010(3) 1.5361(3) 0.0364(6) Uani 1 1 d . . . . .
Cl1 Cl 0.60406(11) 0.59412(9) 0.85902(8) 0.02295(19) Uani 1 1 d . . . . .
Cu1 Cu 0.73667(6) 0.48240(4) 1.03982(4) 0.02076(15) 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
C1 N1 1.352(4) . ?
C1 C2 1.375(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.379(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(4) . ?
C4 H4 0.9500 . ?
C5 N1 1.344(4) . ?
C5 C6 1.497(4) . ?
C6 N2 1.473(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.302(4) . ?
C7 C8 1.412(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.410(5) . ?
C8 C11 1.478(4) . ?
C9 O1 1.283(4) . ?
C9 C10 1.504(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O2 1.222(4) . ?
C11 C12 1.518(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N1 Cu1 1.998(3) . ?
N2 Cu1 1.926(3) . ?
O1 Cu1 1.928(2) . ?
Cl1 Cu1 2.2907(8) . ?

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
N1 C1 C2 122.5(3) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C1 C2 C3 118.4(3) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
N1 C5 C4 121.8(3) . . ?
N1 C5 C6 116.6(3) . . ?
C4 C5 C6 121.6(3) . . ?
N2 C6 C5 109.6(3) . . ?
N2 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 126.8(3) . . ?
N2 C7 H7 116.6 . . ?
C8 C7 H7 116.6 . . ?
C9 C8 C7 121.3(3) . . ?
C9 C8 C11 121.5(3) . . ?
C7 C8 C11 117.2(3) . . ?
O1 C9 C8 123.3(3) . . ?
O1 C9 C10 113.7(3) . . ?
C8 C9 C10 123.0(3) . . ?
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 . . ?
O2 C11 C8 123.1(3) . . ?
O2 C11 C12 118.0(3) . . ?
C8 C11 C12 118.9(3) . . ?
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 . . ?
C5 N1 C1 118.8(3) . . ?
C5 N1 Cu1 114.8(2) . . ?
C1 N1 Cu1 126.4(2) . . ?
C7 N2 C6 116.8(3) . . ?
C7 N2 Cu1 127.4(2) . . ?
C6 N2 Cu1 115.9(2) . . ?
C9 O1 Cu1 131.1(2) . . ?
N2 Cu1 O1 89.75(10) . . ?
N2 Cu1 N1 83.01(11) . . ?
O1 Cu1 N1 172.54(10) . . ?
N2 Cu1 Cl1 164.65(9) . . ?
O1 Cu1 Cl1 90.42(7) . . ?
N1 Cu1 Cl1 96.08(8) . . ?

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
N1 C1 C2 C3 0.6(6) . . . . ?
C1 C2 C3 C4 -0.2(6) . . . . ?
C2 C3 C4 C5 -0.2(6) . . . . ?
C3 C4 C5 N1 0.2(5) . . . . ?
C3 C4 C5 C6 179.7(3) . . . . ?
N1 C5 C6 N2 -3.1(4) . . . . ?
C4 C5 C6 N2 177.5(3) . . . . ?
N2 C7 C8 C9 -1.5(6) . . . . ?
N2 C7 C8 C11 177.8(3) . . . . ?
C7 C8 C9 O1 -3.8(6) . . . . ?
C11 C8 C9 O1 176.9(3) . . . . ?
C7 C8 C9 C10 177.2(3) . . . . ?
C11 C8 C9 C10 -2.0(5) . . . . ?
C9 C8 C11 O2 16.0(6) . . . . ?
C7 C8 C11 O2 -163.3(4) . . . . ?
C9 C8 C11 C12 -163.7(4) . . . . ?
C7 C8 C11 C12 17.0(5) . . . . ?
C4 C5 N1 C1 0.1(5) . . . . ?
C6 C5 N1 C1 -179.3(3) . . . . ?
C4 C5 N1 Cu1 -179.7(3) . . . . ?
C6 C5 N1 Cu1 0.8(4) . . . . ?
C2 C1 N1 C5 -0.6(5) . . . . ?
C2 C1 N1 Cu1 179.3(3) . . . . ?
C8 C7 N2 C6 -176.2(3) . . . . ?
C8 C7 N2 Cu1 3.3(5) . . . . ?
C5 C6 N2 C7 -176.5(3) . . . . ?
C5 C6 N2 Cu1 4.0(4) . . . . ?
C8 C9 O1 Cu1 7.3(5) . . . . ?
C10 C9 O1 Cu1 -173.6(2) . . . . ?

_refine_diff_density_max         0.835
_refine_diff_density_min         -0.960
_refine_diff_density_rms         0.119

####################################################################### 
# 
# 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_cl114
_database_code_depnum_ccdc_archive 'CCDC 1566625'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;


# start Validation Reply Form
_vrf_RINTA01_cl114               
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: Crystal of low quality, will only be discussed as motif.
;
_vrf_PLAT020_cl114               
;
PROBLEM: The value of Rint is greater than 0.12 .........      0.294 Report
RESPONSE: Crystal of low quality, will only be discussed as motif.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;
_chemical_name_common            '[CuL30cCl]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 Cl Cu N2 O4'
_chemical_formula_sum            'C14 H17 Cl Cu N2 O4'
_chemical_formula_weight         376.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   10.9871(5)
_cell_length_b                   20.1512(12)
_cell_length_c                   13.9510(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.232(3)
_cell_angle_gamma                90
_cell_volume                     3080.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    10686
_cell_measurement_theta_min      1.78
_cell_measurement_theta_max      28.59

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_F_000             1544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.094
_exptl_absorpt_coefficient_mu    1.610
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            18260
_diffrn_reflns_av_unetI/netI     0.1956
_diffrn_reflns_av_R_equivalents  0.2943
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.779
_diffrn_reflns_theta_max         28.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             7232
_reflns_number_gt                4234
_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1730P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7232
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0711
_refine_ls_wR_factor_ref         0.2785
_refine_ls_wR_factor_gt          0.1847
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_restrained_S_all      0.956
_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
C11 C 0.2296(6) 0.2543(4) -0.1522(5) 0.0259(14) Uani 1 1 d . . . . .
H11 H 0.1671 0.2823 -0.1314 0.031 Uiso 1 1 calc R U . . .
C12 C 0.2792(6) 0.2690(4) -0.2376(5) 0.0261(15) Uani 1 1 d . . . . .
H12 H 0.2527 0.3070 -0.2736 0.031 Uiso 1 1 calc R U . . .
C13 C 0.3680(6) 0.2277(4) -0.2701(5) 0.0271(15) Uani 1 1 d . . . . .
H13 H 0.4038 0.2371 -0.3286 0.032 Uiso 1 1 calc R U . . .
C14 C 0.4038(5) 0.1728(4) -0.2162(5) 0.0217(13) Uani 1 1 d . . . . .
H14 H 0.4632 0.1430 -0.2375 0.026 Uiso 1 1 calc R U . . .
C15 C 0.3507(5) 0.1618(3) -0.1293(5) 0.0183(12) Uani 1 1 d . . . . .
C16 C 0.3884(6) 0.1046(4) -0.0654(4) 0.0229(14) Uani 1 1 d . . . . .
H16A H 0.3816 0.0629 -0.1028 0.028 Uiso 1 1 calc R U . . .
H16B H 0.4746 0.1102 -0.0409 0.028 Uiso 1 1 calc R U . . .
C17 C 0.3316(5) 0.0528(3) 0.0768(4) 0.0185(12) Uani 1 1 d . . . . .
H17 H 0.3914 0.0211 0.0618 0.022 Uiso 1 1 calc R U . . .
C18 C 0.2752(5) 0.0425(3) 0.1630(4) 0.0164(12) Uani 1 1 d . . . . .
C19 C 0.1820(5) 0.0850(3) 0.1906(4) 0.0150(11) Uani 1 1 d . . . . .
C20 C 0.0287(6) 0.1130(4) 0.2953(5) 0.0240(14) Uani 1 1 d . . . . .
H20A H -0.0408 0.1114 0.2460 0.029 Uiso 1 1 calc R U . . .
H20B H 0.0579 0.1594 0.3014 0.029 Uiso 1 1 calc R U . . .
C21 C -0.0097(6) 0.0878(4) 0.3910(6) 0.0338(17) Uani 1 1 d . . . . .
H21A H -0.0357 0.0414 0.3843 0.051 Uiso 1 1 calc R U . . .
H21B H -0.0776 0.1148 0.4112 0.051 Uiso 1 1 calc R U . . .
H21C H 0.0594 0.0910 0.4395 0.051 Uiso 1 1 calc R U . . .
C22 C 0.3177(5) -0.0186(3) 0.2146(4) 0.0181(12) Uani 1 1 d . . . . .
C23 C 0.3167(6) -0.0843(3) 0.3540(5) 0.0218(13) Uani 1 1 d . . . . .
H23A H 0.4040 -0.0802 0.3762 0.026 Uiso 1 1 calc R U . . .
H23B H 0.3063 -0.1240 0.3123 0.026 Uiso 1 1 calc R U . . .
C24 C 0.2390(6) -0.0904(4) 0.4395(5) 0.0312(16) Uani 1 1 d . . . . .
H24A H 0.2405 -0.0483 0.4748 0.047 Uiso 1 1 calc R U . . .
H24B H 0.2716 -0.1258 0.4821 0.047 Uiso 1 1 calc R U . . .
H24C H 0.1547 -0.1010 0.4166 0.047 Uiso 1 1 calc R U . . .
C31 C 0.2756(5) 0.2555(3) 0.3093(5) 0.0230(14) Uani 1 1 d . . . . .
H31 H 0.2854 0.2796 0.2518 0.028 Uiso 1 1 calc R U . . .
C32 C 0.1987(6) 0.2808(4) 0.3728(5) 0.0238(14) Uani 1 1 d . . . . .
H32 H 0.1558 0.3211 0.3598 0.029 Uiso 1 1 calc R U . . .
C33 C 0.1856(6) 0.2456(4) 0.4568(5) 0.0254(14) Uani 1 1 d . . . . .
H33 H 0.1313 0.2611 0.5017 0.030 Uiso 1 1 calc R U . . .
C34 C 0.2510(5) 0.1884(4) 0.4753(5) 0.0224(13) Uani 1 1 d . . . . .
H34 H 0.2443 0.1646 0.5334 0.027 Uiso 1 1 calc R U . . .
C35 C 0.3275(5) 0.1660(3) 0.4065(5) 0.0184(12) Uani 1 1 d . . . . .
C36 C 0.4029(5) 0.1043(3) 0.4223(4) 0.0194(12) Uani 1 1 d . . . . .
H36A H 0.4529 0.1075 0.4841 0.023 Uiso 1 1 calc R U . . .
H36B H 0.3487 0.0652 0.4251 0.023 Uiso 1 1 calc R U . . .
C37 C 0.5611(5) 0.0474(3) 0.3509(4) 0.0177(12) Uani 1 1 d . . . . .
H37 H 0.5585 0.0200 0.4061 0.021 Uiso 1 1 calc R U . . .
C38 C 0.6498(5) 0.0312(4) 0.2847(4) 0.0194(13) Uani 1 1 d . . . . .
C39 C 0.6555(5) 0.0677(3) 0.1983(4) 0.0161(11) Uani 1 1 d . . . . .
C40 C 0.7576(6) 0.0929(4) 0.0568(5) 0.0248(14) Uani 1 1 d . . . . .
H40A H 0.7602 0.1408 0.0726 0.030 Uiso 1 1 calc R U . . .
H40B H 0.6879 0.0847 0.0092 0.030 Uiso 1 1 calc R U . . .
C41 C 0.8757(6) 0.0713(4) 0.0175(5) 0.0314(17) Uani 1 1 d . . . . .
H41A H 0.9439 0.0811 0.0647 0.047 Uiso 1 1 calc R U . . .
H41B H 0.8871 0.0954 -0.0423 0.047 Uiso 1 1 calc R U . . .
H41C H 0.8729 0.0235 0.0045 0.047 Uiso 1 1 calc R U . . .
C42 C 0.7274(5) -0.0242(3) 0.3184(5) 0.0215(13) Uani 1 1 d . . . . .
C43 C 0.8933(5) -0.0954(4) 0.2889(5) 0.0247(14) Uani 1 1 d . . . . .
H43A H 0.8472 -0.1374 0.2933 0.030 Uiso 1 1 calc R U . . .
H43B H 0.9344 -0.0855 0.3529 0.030 Uiso 1 1 calc R U . . .
C44 C 0.9859(6) -0.1015(4) 0.2149(6) 0.0312(16) Uani 1 1 d . . . . .
H44A H 0.9443 -0.1132 0.1526 0.047 Uiso 1 1 calc R U . . .
H44B H 1.0452 -0.1361 0.2346 0.047 Uiso 1 1 calc R U . . .
H44C H 1.0283 -0.0590 0.2093 0.047 Uiso 1 1 calc R U . . .
Cl1 Cl 0.06735(15) 0.25699(9) 0.03496(13) 0.0293(4) Uani 1 1 d . . . . .
Cl2 Cl 0.43444(13) 0.23471(8) 0.12224(11) 0.0225(4) Uani 1 1 d . . . . .
Cu1 Cu 0.20451(6) 0.17635(4) 0.02884(5) 0.0169(2) Uani 1 1 d . . . . .
Cu2 Cu 0.45860(6) 0.15941(4) 0.23927(5) 0.0158(2) Uani 1 1 d . . . . .
N11 N 0.2653(4) 0.2022(3) -0.0969(4) 0.0195(11) Uani 1 1 d . . . . .
N12 N 0.3109(4) 0.1007(3) 0.0158(4) 0.0172(10) Uani 1 1 d . . . . .
N31 N 0.3382(4) 0.1986(3) 0.3235(4) 0.0155(10) Uani 1 1 d . . . . .
N32 N 0.4832(4) 0.0965(3) 0.3425(4) 0.0182(11) Uani 1 1 d . . . . .
O11 O 0.1479(4) 0.1369(2) 0.1468(3) 0.0202(9) Uani 1 1 d . . . . .
O12 O 0.1263(4) 0.0697(2) 0.2690(3) 0.0209(10) Uani 1 1 d . . . . .
O13 O 0.3875(4) -0.0580(2) 0.1817(3) 0.0236(10) Uani 1 1 d . . . . .
O14 O 0.2760(4) -0.0259(2) 0.3022(3) 0.0196(9) Uani 1 1 d . . . . .
O31 O 0.5844(4) 0.1142(2) 0.1706(3) 0.0191(9) Uani 1 1 d . . . . .
O32 O 0.7458(4) 0.0533(3) 0.1434(3) 0.0249(11) Uani 1 1 d . . . . .
O33 O 0.7165(5) -0.0544(3) 0.3932(4) 0.0318(12) Uani 1 1 d . . . . .
O34 O 0.8122(4) -0.0421(3) 0.2585(3) 0.0247(11) 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
C11 N11 1.344(9) . ?
C11 C12 1.379(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(10) . ?
C13 H13 0.9500 . ?
C14 C15 1.401(8) . ?
C14 H14 0.9500 . ?
C15 N11 1.345(8) . ?
C15 C16 1.495(9) . ?
C16 N12 1.468(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 N12 1.297(8) . ?
C17 C18 1.408(8) . ?
C17 H17 0.9500 . ?
C18 C19 1.411(8) . ?
C18 C22 1.484(9) . ?
C19 O11 1.254(8) . ?
C19 O12 1.328(7) . ?
C20 O12 1.450(7) . ?
C20 C21 1.518(9) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 O13 1.217(8) . ?
C22 O14 1.344(7) . ?
C23 O14 1.436(8) . ?
C23 C24 1.523(9) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C31 N31 1.344(8) . ?
C31 C32 1.366(8) . ?
C31 H31 0.9500 . ?
C32 C33 1.387(10) . ?
C32 H32 0.9500 . ?
C33 C34 1.372(10) . ?
C33 H33 0.9500 . ?
C34 C35 1.396(9) . ?
C34 H34 0.9500 . ?
C35 N31 1.345(8) . ?
C35 C36 1.501(9) . ?
C36 N32 1.479(7) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 N32 1.308(8) . ?
C37 C38 1.429(8) . ?
C37 H37 0.9500 . ?
C38 C39 1.418(9) . ?
C38 C42 1.462(9) . ?
C39 O31 1.261(8) . ?
C39 O32 1.330(7) . ?
C40 O32 1.462(8) . ?
C40 C41 1.510(8) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 O33 1.221(8) . ?
C42 O34 1.346(7) . ?
C43 O34 1.439(8) . ?
C43 C44 1.508(9) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
Cl1 Cu1 2.2221(16) . ?
Cl2 Cu2 2.2304(17) . ?
Cu1 N12 1.938(5) . ?
Cu1 O11 1.970(4) . ?
Cu1 N11 1.992(5) . ?
Cu2 N32 1.923(5) . ?
Cu2 O31 1.964(4) . ?
Cu2 N31 1.996(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N11 C11 C12 123.1(6) . . ?
N11 C11 H11 118.4 . . ?
C12 C11 H11 118.4 . . ?
C11 C12 C13 119.2(7) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C14 C13 C12 118.9(6) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 118.6(6) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
N11 C15 C14 122.7(6) . . ?
N11 C15 C16 115.8(5) . . ?
C14 C15 C16 121.5(6) . . ?
N12 C16 C15 110.5(5) . . ?
N12 C16 H16A 109.5 . . ?
C15 C16 H16A 109.5 . . ?
N12 C16 H16B 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
N12 C17 C18 127.1(6) . . ?
N12 C17 H17 116.4 . . ?
C18 C17 H17 116.4 . . ?
C17 C18 C19 121.2(6) . . ?
C17 C18 C22 113.2(5) . . ?
C19 C18 C22 125.5(5) . . ?
O11 C19 O12 117.1(5) . . ?
O11 C19 C18 124.8(5) . . ?
O12 C19 C18 118.2(5) . . ?
O12 C20 C21 106.3(6) . . ?
O12 C20 H20A 110.5 . . ?
C21 C20 H20A 110.5 . . ?
O12 C20 H20B 110.5 . . ?
C21 C20 H20B 110.5 . . ?
H20A C20 H20B 108.7 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O13 C22 O14 122.7(6) . . ?
O13 C22 C18 122.8(5) . . ?
O14 C22 C18 114.5(5) . . ?
O14 C23 C24 106.8(5) . . ?
O14 C23 H23A 110.4 . . ?
C24 C23 H23A 110.4 . . ?
O14 C23 H23B 110.4 . . ?
C24 C23 H23B 110.4 . . ?
H23A C23 H23B 108.6 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N31 C31 C32 123.8(7) . . ?
N31 C31 H31 118.1 . . ?
C32 C31 H31 118.1 . . ?
C31 C32 C33 117.7(6) . . ?
C31 C32 H32 121.2 . . ?
C33 C32 H32 121.2 . . ?
C34 C33 C32 120.2(6) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C33 C34 C35 118.4(6) . . ?
C33 C34 H34 120.8 . . ?
C35 C34 H34 120.8 . . ?
N31 C35 C34 121.9(6) . . ?
N31 C35 C36 116.7(5) . . ?
C34 C35 C36 121.4(6) . . ?
N32 C36 C35 109.3(5) . . ?
N32 C36 H36A 109.8 . . ?
C35 C36 H36A 109.8 . . ?
N32 C36 H36B 109.8 . . ?
C35 C36 H36B 109.8 . . ?
H36A C36 H36B 108.3 . . ?
N32 C37 C38 126.0(6) . . ?
N32 C37 H37 117.0 . . ?
C38 C37 H37 117.0 . . ?
C39 C38 C37 120.4(6) . . ?
C39 C38 C42 127.5(5) . . ?
C37 C38 C42 112.1(6) . . ?
O31 C39 O32 117.2(6) . . ?
O31 C39 C38 125.5(5) . . ?
O32 C39 C38 117.3(6) . . ?
O32 C40 C41 105.9(6) . . ?
O32 C40 H40A 110.6 . . ?
C41 C40 H40A 110.6 . . ?
O32 C40 H40B 110.6 . . ?
C41 C40 H40B 110.6 . . ?
H40A C40 H40B 108.7 . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
O33 C42 O34 120.9(6) . . ?
O33 C42 C38 124.3(6) . . ?
O34 C42 C38 114.7(6) . . ?
O34 C43 C44 107.0(5) . . ?
O34 C43 H43A 110.3 . . ?
C44 C43 H43A 110.3 . . ?
O34 C43 H43B 110.3 . . ?
C44 C43 H43B 110.3 . . ?
H43A C43 H43B 108.6 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
N12 Cu1 O11 89.5(2) . . ?
N12 Cu1 N11 83.0(2) . . ?
O11 Cu1 N11 171.3(2) . . ?
N12 Cu1 Cl1 173.94(17) . . ?
O11 Cu1 Cl1 90.37(14) . . ?
N11 Cu1 Cl1 96.60(17) . . ?
N32 Cu2 O31 89.7(2) . . ?
N32 Cu2 N31 83.3(2) . . ?
O31 Cu2 N31 172.8(2) . . ?
N32 Cu2 Cl2 178.08(18) . . ?
O31 Cu2 Cl2 90.51(14) . . ?
N31 Cu2 Cl2 96.50(16) . . ?
C11 N11 C15 117.5(5) . . ?
C11 N11 Cu1 127.3(4) . . ?
C15 N11 Cu1 115.1(4) . . ?
C17 N12 C16 117.6(5) . . ?
C17 N12 Cu1 127.0(4) . . ?
C16 N12 Cu1 114.7(4) . . ?
C31 N31 C35 117.9(5) . . ?
C31 N31 Cu2 127.2(4) . . ?
C35 N31 Cu2 114.6(4) . . ?
C37 N32 C36 115.9(5) . . ?
C37 N32 Cu2 128.4(4) . . ?
C36 N32 Cu2 115.8(4) . . ?
C19 O11 Cu1 130.0(4) . . ?
C19 O12 C20 117.6(5) . . ?
C22 O14 C23 115.6(5) . . ?
C39 O31 Cu2 129.6(4) . . ?
C39 O32 C40 118.2(5) . . ?
C42 O34 C43 117.2(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N11 C11 C12 C13 1.7(12) . . . . ?
C11 C12 C13 C14 0.3(12) . . . . ?
C12 C13 C14 C15 -1.5(11) . . . . ?
C13 C14 C15 N11 0.8(10) . . . . ?
C13 C14 C15 C16 -177.7(6) . . . . ?
N11 C15 C16 N12 6.9(8) . . . . ?
C14 C15 C16 N12 -174.5(6) . . . . ?
N12 C17 C18 C19 2.4(10) . . . . ?
N12 C17 C18 C22 178.2(6) . . . . ?
C17 C18 C19 O11 -5.5(10) . . . . ?
C22 C18 C19 O11 179.2(6) . . . . ?
C17 C18 C19 O12 175.1(6) . . . . ?
C22 C18 C19 O12 -0.2(9) . . . . ?
C17 C18 C22 O13 -5.1(9) . . . . ?
C19 C18 C22 O13 170.5(6) . . . . ?
C17 C18 C22 O14 172.8(5) . . . . ?
C19 C18 C22 O14 -11.5(9) . . . . ?
N31 C31 C32 C33 0.4(11) . . . . ?
C31 C32 C33 C34 1.7(10) . . . . ?
C32 C33 C34 C35 -1.7(10) . . . . ?
C33 C34 C35 N31 -0.3(10) . . . . ?
C33 C34 C35 C36 179.3(6) . . . . ?
N31 C35 C36 N32 5.0(8) . . . . ?
C34 C35 C36 N32 -174.6(6) . . . . ?
N32 C37 C38 C39 -3.0(10) . . . . ?
N32 C37 C38 C42 176.6(6) . . . . ?
C37 C38 C39 O31 -2.5(10) . . . . ?
C42 C38 C39 O31 178.0(6) . . . . ?
C37 C38 C39 O32 175.2(6) . . . . ?
C42 C38 C39 O32 -4.4(10) . . . . ?
C39 C38 C42 O33 -178.7(7) . . . . ?
C37 C38 C42 O33 1.7(10) . . . . ?
C39 C38 C42 O34 -1.0(10) . . . . ?
C37 C38 C42 O34 179.4(6) . . . . ?
C12 C11 N11 C15 -2.4(11) . . . . ?
C12 C11 N11 Cu1 178.5(6) . . . . ?
C14 C15 N11 C11 1.1(10) . . . . ?
C16 C15 N11 C11 179.7(6) . . . . ?
C14 C15 N11 Cu1 -179.6(5) . . . . ?
C16 C15 N11 Cu1 -1.1(7) . . . . ?
C18 C17 N12 C16 174.9(6) . . . . ?
C18 C17 N12 Cu1 4.8(10) . . . . ?
C15 C16 N12 C17 179.0(6) . . . . ?
C15 C16 N12 Cu1 -9.7(7) . . . . ?
C32 C31 N31 C35 -2.4(10) . . . . ?
C32 C31 N31 Cu2 -176.8(5) . . . . ?
C34 C35 N31 C31 2.3(9) . . . . ?
C36 C35 N31 C31 -177.3(6) . . . . ?
C34 C35 N31 Cu2 177.4(5) . . . . ?
C36 C35 N31 Cu2 -2.2(7) . . . . ?
C38 C37 N32 C36 -178.2(6) . . . . ?
C38 C37 N32 Cu2 2.3(10) . . . . ?
C35 C36 N32 C37 174.8(6) . . . . ?
C35 C36 N32 Cu2 -5.7(7) . . . . ?
O12 C19 O11 Cu1 -179.3(4) . . . . ?
C18 C19 O11 Cu1 1.2(9) . . . . ?
O11 C19 O12 C20 1.9(8) . . . . ?
C18 C19 O12 C20 -178.6(6) . . . . ?
C21 C20 O12 C19 -174.9(6) . . . . ?
O13 C22 O14 C23 -1.6(9) . . . . ?
C18 C22 O14 C23 -179.5(5) . . . . ?
C24 C23 O14 C22 -168.1(6) . . . . ?
O32 C39 O31 Cu2 -169.3(4) . . . . ?
C38 C39 O31 Cu2 8.3(9) . . . . ?
O31 C39 O32 C40 1.3(9) . . . . ?
C38 C39 O32 C40 -176.5(6) . . . . ?
C41 C40 O32 C39 172.7(6) . . . . ?
O33 C42 O34 C43 -3.6(10) . . . . ?
C38 C42 O34 C43 178.5(6) . . . . ?
C44 C43 O34 C42 -174.7(6) . . . . ?

_refine_diff_density_max         1.511
_refine_diff_density_min         -1.948
_refine_diff_density_rms         0.257

####################################################################### 
# 
# 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_cl116
_database_code_depnum_ccdc_archive 'CCDC 1566620'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;
_chemical_name_common            '[CuL30bNO3]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H15 Cu N3 O6, H2 O'
_chemical_formula_sum            'C12 H17 Cu N3 O7'
_chemical_formula_weight         378.82

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'

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

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

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

_cell_length_a                   8.7846(4)
_cell_length_b                   18.8515(6)
_cell_length_c                   9.0280(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.363(3)
_cell_angle_gamma                90
_cell_volume                     1475.14(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    15949
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      27.65

_exptl_crystal_description       hexagon
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_F_000             780
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.145
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.096
_exptl_absorpt_coefficient_mu    1.523
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            17951
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.161
_diffrn_reflns_theta_max         28.501
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3572
_reflns_number_gt                3105
_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²+0.1748P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3572
_refine_ls_number_parameters     224
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0663
_refine_ls_wR_factor_gt          0.0639
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.031
_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
C1 C 0.73830(19) 0.19473(9) 0.46339(17) 0.0220(3) Uani 1 1 d . . . . .
H1 H 0.6661 0.2140 0.3838 0.026 Uiso 1 1 calc R U . . .
C2 C 0.8383(2) 0.24004(9) 0.55126(18) 0.0252(3) Uani 1 1 d . . . . .
H2 H 0.8346 0.2897 0.5333 0.030 Uiso 1 1 calc R U . . .
C3 C 0.9444(2) 0.21146(9) 0.66648(17) 0.0230(3) Uani 1 1 d . . . . .
H3 H 1.0144 0.2415 0.7288 0.028 Uiso 1 1 calc R U . . .
C4 C 0.94734(18) 0.13922(9) 0.68977(16) 0.0205(3) Uani 1 1 d . . . . .
H4 H 1.0201 0.1188 0.7673 0.025 Uiso 1 1 calc R U . . .
C5 C 0.84218(17) 0.09671(8) 0.59801(15) 0.0165(3) Uani 1 1 d . . . . .
C6 C 0.83718(18) 0.01772(8) 0.62002(16) 0.0194(3) Uani 1 1 d . . . . .
H6A H 0.9413 -0.0026 0.6211 0.023 Uiso 1 1 calc R U . . .
H6B H 0.8045 0.0070 0.7175 0.023 Uiso 1 1 calc R U . . .
C7 C 0.71706(17) -0.08272(8) 0.49265(15) 0.0165(3) Uani 1 1 d . . . . .
H7 H 0.7804 -0.1083 0.5699 0.020 Uiso 1 1 calc R U . . .
C8 C 0.61919(17) -0.12385(8) 0.38276(15) 0.0161(3) Uani 1 1 d . . . . .
C9 C 0.52019(17) -0.09055(8) 0.26179(15) 0.0163(3) Uani 1 1 d . . . . .
C10 C 0.41895(19) -0.13118(9) 0.14145(17) 0.0215(3) Uani 1 1 d . . . . .
H10A H 0.3694 -0.0982 0.0644 0.032 Uiso 1 1 calc R U . . .
H10B H 0.3396 -0.1565 0.1853 0.032 Uiso 1 1 calc R U . . .
H10C H 0.4815 -0.1654 0.0959 0.032 Uiso 1 1 calc R U . . .
C11 C 0.62278(18) -0.20074(8) 0.40175(16) 0.0174(3) Uani 1 1 d . . . . .
C12 C 0.7360(2) -0.23375(9) 0.52694(18) 0.0227(3) Uani 1 1 d . . . . .
H12A H 0.7060 -0.2219 0.6239 0.034 Uiso 1 1 calc R U . . .
H12B H 0.8398 -0.2154 0.5236 0.034 Uiso 1 1 calc R U . . .
H12C H 0.7357 -0.2854 0.5144 0.034 Uiso 1 1 calc R U . . .
N1 N 0.73955(15) 0.12415(7) 0.48656(13) 0.0168(2) Uani 1 1 d . . . . .
N2 N 0.72827(15) -0.01402(7) 0.49778(13) 0.0164(2) Uani 1 1 d . . . . .
N11 N 0.90322(15) 0.08242(7) 0.15689(14) 0.0195(3) Uani 1 1 d . . . . .
O1 O 0.50931(13) -0.02357(6) 0.24634(11) 0.0193(2) Uani 1 1 d . . . . .
O2 O 0.53382(15) -0.24117(6) 0.32088(13) 0.0261(3) Uani 1 1 d . . . . .
O11 O 0.79361(15) 0.04312(7) 0.18200(13) 0.0276(3) Uani 1 1 d . . . . .
O12 O 0.97080(15) 0.12169(6) 0.25691(13) 0.0278(3) Uani 1 1 d . . . . .
O13 O 0.94105(14) 0.08078(7) 0.02945(13) 0.0282(3) Uani 1 1 d . . . . .
O21 O 0.47360(14) 0.11610(6) 0.23447(13) 0.0216(2) Uani 1 1 d D . . . .
O31 O 0.25690(16) 0.07546(7) 0.01360(14) 0.0247(3) Uani 1 1 d . . . . .
Cu1 Cu 0.62093(2) 0.05207(2) 0.35620(2) 0.01486(7) Uani 1 1 d . . . . .
H21A H 0.411(2) 0.1010(14) 0.172(2) 0.045(7) Uiso 1 1 d D . . . .
H21B H 0.482(3) 0.1560(14) 0.210(3) 0.038(6) Uiso 1 1 d . . . . .
H31A H 0.175(3) 0.0808(13) 0.024(2) 0.030(6) Uiso 1 1 d . . . . .
H31B H 0.253(3) 0.0360(17) -0.024(3) 0.051(8) Uiso 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
C1 N1 1.347(2) . ?
C1 C2 1.380(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.388(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(2) . ?
C4 H4 0.9500 . ?
C5 N1 1.3408(18) . ?
C5 C6 1.504(2) . ?
C6 N2 1.4655(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.299(2) . ?
C7 C8 1.431(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.4262(19) . ?
C8 C11 1.459(2) . ?
C9 O1 1.2723(19) . ?
C9 C10 1.498(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O2 1.2405(19) . ?
C11 C12 1.513(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N1 Cu1 1.9796(12) . ?
N2 Cu1 1.9191(12) . ?
N11 O12 1.2416(18) . ?
N11 O13 1.2488(17) . ?
N11 O11 1.2644(18) . ?
O1 Cu1 1.9136(11) . ?
O11 Cu1 2.3620(12) . ?
O21 Cu1 1.9691(11) . ?
O21 H21A 0.778(17) . ?
O21 H21B 0.79(3) . ?
O31 H31A 0.75(3) . ?
O31 H31B 0.81(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.28(14) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C1 C2 C3 118.53(15) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 119.48(14) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 118.99(14) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.68(14) . . ?
N1 C5 C6 116.79(12) . . ?
C4 C5 C6 121.53(13) . . ?
N2 C6 C5 109.53(11) . . ?
N2 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
N2 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 126.76(13) . . ?
N2 C7 H7 116.6 . . ?
C8 C7 H7 116.6 . . ?
C9 C8 C7 121.02(14) . . ?
C9 C8 C11 121.73(13) . . ?
C7 C8 C11 117.24(13) . . ?
O1 C9 C8 123.11(13) . . ?
O1 C9 C10 113.76(12) . . ?
C8 C9 C10 123.13(14) . . ?
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 . . ?
O2 C11 C8 122.79(14) . . ?
O2 C11 C12 117.49(13) . . ?
C8 C11 C12 119.70(13) . . ?
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 . . ?
C5 N1 C1 119.04(13) . . ?
C5 N1 Cu1 113.94(10) . . ?
C1 N1 Cu1 126.56(10) . . ?
C7 N2 C6 118.06(12) . . ?
C7 N2 Cu1 126.67(10) . . ?
C6 N2 Cu1 115.23(10) . . ?
O12 N11 O13 121.16(14) . . ?
O12 N11 O11 120.47(13) . . ?
O13 N11 O11 118.37(13) . . ?
C9 O1 Cu1 131.28(9) . . ?
N11 O11 Cu1 131.90(10) . . ?
Cu1 O21 H21A 120(2) . . ?
Cu1 O21 H21B 131.1(18) . . ?
H21A O21 H21B 103(3) . . ?
H31A O31 H31B 101(3) . . ?
O1 Cu1 N2 90.94(5) . . ?
O1 Cu1 O21 86.14(5) . . ?
N2 Cu1 O21 167.65(5) . . ?
O1 Cu1 N1 174.53(5) . . ?
N2 Cu1 N1 84.01(5) . . ?
O21 Cu1 N1 98.37(5) . . ?
O1 Cu1 O11 86.11(4) . . ?
N2 Cu1 O11 95.62(5) . . ?
O21 Cu1 O11 96.15(5) . . ?
N1 Cu1 O11 96.43(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.6(3) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C3 C4 C5 N1 0.8(2) . . . . ?
C3 C4 C5 C6 -178.57(14) . . . . ?
N1 C5 C6 N2 6.96(18) . . . . ?
C4 C5 C6 N2 -173.59(13) . . . . ?
N2 C7 C8 C9 0.3(2) . . . . ?
N2 C7 C8 C11 -178.40(14) . . . . ?
C7 C8 C9 O1 -2.0(2) . . . . ?
C11 C8 C9 O1 176.62(14) . . . . ?
C7 C8 C9 C10 178.19(14) . . . . ?
C11 C8 C9 C10 -3.2(2) . . . . ?
C9 C8 C11 O2 -4.9(2) . . . . ?
C7 C8 C11 O2 173.82(14) . . . . ?
C9 C8 C11 C12 176.67(13) . . . . ?
C7 C8 C11 C12 -4.6(2) . . . . ?
C4 C5 N1 C1 -0.2(2) . . . . ?
C6 C5 N1 C1 179.29(14) . . . . ?
C4 C5 N1 Cu1 172.61(11) . . . . ?
C6 C5 N1 Cu1 -7.94(16) . . . . ?
C2 C1 N1 C5 -0.6(2) . . . . ?
C2 C1 N1 Cu1 -172.33(12) . . . . ?
C8 C7 N2 C6 -179.54(14) . . . . ?
C8 C7 N2 Cu1 -1.9(2) . . . . ?
C5 C6 N2 C7 175.24(13) . . . . ?
C5 C6 N2 Cu1 -2.69(15) . . . . ?
C8 C9 O1 Cu1 5.5(2) . . . . ?
C10 C9 O1 Cu1 -174.70(10) . . . . ?
O12 N11 O11 Cu1 24.8(2) . . . . ?
O13 N11 O11 Cu1 -155.06(11) . . . . ?

_refine_diff_density_max         0.369
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.080

####################################################################### 
# 
# 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_cl118
_database_code_depnum_ccdc_archive 'CCDC 1566621'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;
_chemical_name_common            '[CuL30dNO3]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 Cu N3 O3, N O3, H2 O'
_chemical_formula_sum            'C12 H16 Cu N4 O7'
_chemical_formula_weight         391.83

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                   9.0597(6)
_cell_length_b                   14.5372(7)
_cell_length_c                   11.8354(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.232(5)
_cell_angle_gamma                90
_cell_volume                     1552.26(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    8319
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      28.52

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_F_000             804
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.083
_exptl_absorpt_coefficient_mu    1.452
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;??
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            11415
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.225
_diffrn_reflns_theta_max         28.533
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3688
_reflns_number_gt                2876
_reflns_threshold_expression     'I > 2σ(I)'

_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0305P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3688
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0605
_refine_ls_wR_factor_gt          0.0578
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_restrained_S_all      0.906
_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
C1 C 0.2223(2) -0.11827(13) 0.50565(16) 0.0212(4) Uani 1 1 d . . . . .
H1 H 0.1759 -0.1648 0.5462 0.025 Uiso 1 1 calc R U . . .
C2 C 0.3064(2) -0.14371(14) 0.41928(18) 0.0252(4) Uani 1 1 d . . . . .
H2 H 0.3169 -0.2067 0.4003 0.030 Uiso 1 1 calc R U . . .
C3 C 0.3751(2) -0.07608(15) 0.36071(18) 0.0282(4) Uani 1 1 d . . . . .
H3 H 0.4353 -0.0921 0.3021 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3549(2) 0.01496(15) 0.38867(17) 0.0276(4) Uani 1 1 d . . . . .
H4 H 0.3996 0.0625 0.3485 0.033 Uiso 1 1 calc R U . . .
C5 C 0.26831(19) 0.03638(12) 0.47615(15) 0.0186(4) Uani 1 1 d . . . . .
C6 C 0.2458(2) 0.13376(12) 0.51319(17) 0.0206(4) Uani 1 1 d . . . . .
H6A H 0.3427 0.1616 0.5394 0.025 Uiso 1 1 calc R U . . .
H6B H 0.2011 0.1704 0.4483 0.025 Uiso 1 1 calc R U . . .
C7 C 0.10692(18) 0.21495(12) 0.63979(15) 0.0170(3) Uani 1 1 d . . . . .
H7 H 0.1336 0.2677 0.5989 0.020 Uiso 1 1 calc R U . . .
C8 C 0.02427(18) 0.22889(12) 0.73457(16) 0.0174(4) Uani 1 1 d . . . . .
C9 C -0.01571(18) 0.15647(12) 0.80684(16) 0.0174(4) Uani 1 1 d . . . . .
C10 C -0.1263(2) 0.11427(13) 0.97572(17) 0.0253(4) Uani 1 1 d . . . . .
H10A H -0.1501 0.1448 1.0466 0.030 Uiso 1 1 calc R U . . .
H10B H -0.0407 0.0730 0.9947 0.030 Uiso 1 1 calc R U . . .
C11 C -0.2566(3) 0.05809(17) 0.9298(2) 0.0388(6) Uani 1 1 d . . . . .
H11A H -0.3410 0.0988 0.9090 0.058 Uiso 1 1 calc R U . . .
H11B H -0.2828 0.0144 0.9878 0.058 Uiso 1 1 calc R U . . .
H11C H -0.2313 0.0243 0.8625 0.058 Uiso 1 1 calc R U . . .
C12 C 0.01086(19) -0.17969(12) 0.73679(15) 0.0174(4) Uani 1 1 d . . . . .
N1 N 0.20400(15) -0.02962(10) 0.53438(13) 0.0173(3) Uani 1 1 d . . . . .
N2 N 0.14849(15) 0.13545(10) 0.60520(13) 0.0168(3) Uani 1 1 d . . . . .
N3 N 0.03740(16) -0.10552(10) 0.71328(14) 0.0205(3) Uani 1 1 d . . . . .
N21 N 0.50770(17) 0.30291(11) 0.72245(15) 0.0236(3) Uani 1 1 d . . . . .
O1 O 0.00961(13) 0.07317(8) 0.79296(11) 0.0196(3) Uani 1 1 d . . . . .
O2 O -0.08484(14) 0.18428(8) 0.89553(11) 0.0215(3) Uani 1 1 d . . . . .
O21 O 0.6047(2) 0.29394(17) 0.79882(17) 0.0634(6) Uani 1 1 d . . . . .
O22 O 0.53063(18) 0.34958(10) 0.63563(13) 0.0339(3) Uani 1 1 d . . . . .
O23 O 0.38883(19) 0.26507(16) 0.72914(18) 0.0619(6) Uani 1 1 d . . . . .
O31 O 0.32650(15) 0.01037(12) 0.77808(13) 0.0234(3) Uani 1 1 d . . . . .
O32 O 0.3425(2) 0.15612(11) 0.92617(17) 0.0324(3) Uani 1 1 d . . . . .
Cu1 Cu 0.11390(2) 0.01643(2) 0.67140(2) 0.01537(6) Uani 1 1 d . . . . .
H31A H 0.336(3) 0.043(2) 0.828(3) 0.041(8) Uiso 1 1 d . . . . .
H31B H 0.358(3) -0.032(2) 0.807(3) 0.049(9) Uiso 1 1 d . . . . .
H32A H 0.391(3) 0.160(2) 0.985(3) 0.054(9) Uiso 1 1 d . . . . .
H32B H 0.376(3) 0.190(2) 0.883(3) 0.054(9) Uiso 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
C1 N1 1.347(2) . ?
C1 C2 1.380(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(2) . ?
C4 H4 0.9500 . ?
C5 N1 1.345(2) . ?
C5 C6 1.501(2) . ?
C6 N2 1.463(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.293(2) . ?
C7 C8 1.419(2) . ?
C7 H7 0.9500 . ?
C8 C12 1.415(2) 2_556 ?
C8 C9 1.424(2) . ?
C9 O1 1.246(2) . ?
C9 O2 1.333(2) . ?
C10 O2 1.464(2) . ?
C10 C11 1.496(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N3 1.145(2) . ?
C12 C8 1.415(2) 2_546 ?
N1 Cu1 1.9964(15) . ?
N2 Cu1 1.9366(14) . ?
N3 Cu1 1.9828(15) . ?
N21 O21 1.209(2) . ?
N21 O23 1.218(2) . ?
N21 O22 1.264(2) . ?
O1 Cu1 1.9726(13) . ?
O31 Cu1 2.2064(14) . ?
O31 H31A 0.76(3) . ?
O31 H31B 0.75(3) . ?
O32 H32A 0.79(3) . ?
O32 H32B 0.79(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.18(18) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C1 C2 C3 119.00(18) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 119.05(18) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 119.32(18) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 121.48(17) . . ?
N1 C5 C6 116.52(15) . . ?
C4 C5 C6 121.98(16) . . ?
N2 C6 C5 109.89(14) . . ?
N2 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 124.59(16) . . ?
N2 C7 H7 117.7 . . ?
C8 C7 H7 117.7 . . ?
C12 C8 C7 118.04(15) 2_556 . ?
C12 C8 C9 118.38(15) 2_556 . ?
C7 C8 C9 123.42(15) . . ?
O1 C9 O2 120.25(16) . . ?
O1 C9 C8 125.40(16) . . ?
O2 C9 C8 114.35(15) . . ?
O2 C10 C11 112.62(17) . . ?
O2 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
O2 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C8 179.13(19) . 2_546 ?
C5 N1 C1 118.95(16) . . ?
C5 N1 Cu1 113.92(12) . . ?
C1 N1 Cu1 126.50(12) . . ?
C7 N2 C6 117.60(15) . . ?
C7 N2 Cu1 127.42(13) . . ?
C6 N2 Cu1 114.64(11) . . ?
C12 N3 Cu1 171.49(14) . . ?
O21 N21 O23 119.3(2) . . ?
O21 N21 O22 120.23(18) . . ?
O23 N21 O22 120.46(18) . . ?
C9 O1 Cu1 127.49(12) . . ?
C9 O2 C10 117.80(14) . . ?
Cu1 O31 H31A 117(2) . . ?
Cu1 O31 H31B 125(2) . . ?
H31A O31 H31B 99(3) . . ?
H32A O32 H32B 108(3) . . ?
N2 Cu1 O1 91.57(6) . . ?
N2 Cu1 N3 166.67(7) . . ?
O1 Cu1 N3 89.42(6) . . ?
N2 Cu1 N1 82.98(6) . . ?
O1 Cu1 N1 172.39(6) . . ?
N3 Cu1 N1 94.67(6) . . ?
N2 Cu1 O31 95.86(6) . . ?
O1 Cu1 O31 92.90(6) . . ?
N3 Cu1 O31 97.36(6) . . ?
N1 Cu1 O31 92.94(6) . . ?

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
N1 C1 C2 C3 0.5(3) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 N1 0.1(3) . . . . ?
C3 C4 C5 C6 178.04(19) . . . . ?
N1 C5 C6 N2 -2.8(2) . . . . ?
C4 C5 C6 N2 179.16(17) . . . . ?
N2 C7 C8 C12 178.93(17) . . . 2_556 ?
N2 C7 C8 C9 3.6(3) . . . . ?
C12 C8 C9 O1 -179.13(17) 2_556 . . . ?
C7 C8 C9 O1 -3.8(3) . . . . ?
C12 C8 C9 O2 0.5(2) 2_556 . . . ?
C7 C8 C9 O2 175.79(16) . . . . ?
C4 C5 N1 C1 -1.1(3) . . . . ?
C6 C5 N1 C1 -179.10(16) . . . . ?
C4 C5 N1 Cu1 170.42(15) . . . . ?
C6 C5 N1 Cu1 -7.6(2) . . . . ?
C2 C1 N1 C5 0.8(3) . . . . ?
C2 C1 N1 Cu1 -169.56(14) . . . . ?
C8 C7 N2 C6 -173.93(16) . . . . ?
C8 C7 N2 Cu1 -0.9(3) . . . . ?
C5 C6 N2 C7 -173.77(16) . . . . ?
C5 C6 N2 Cu1 12.34(19) . . . . ?
O2 C9 O1 Cu1 -178.30(11) . . . . ?
C8 C9 O1 Cu1 1.3(3) . . . . ?
O1 C9 O2 C10 1.2(2) . . . . ?
C8 C9 O2 C10 -178.43(15) . . . . ?
C11 C10 O2 C9 -74.4(2) . . . . ?

_refine_diff_density_max         0.394
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_cl070
_database_code_depnum_ccdc_archive 'CCDC 1566626'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT915_cl070               
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         28 %     
RESPONSE: low quality data
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014/7

_chemical_name_systematic        
;
?
;
_chemical_name_common            '[CuL30fCl]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H17 Cl Cu N2 O3'
_chemical_formula_sum            'C18 H17 Cl Cu N2 O3'
_chemical_formula_weight         408.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 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'

_cell_length_a                   12.9059(7)
_cell_length_b                   18.9389(13)
_cell_length_c                   7.6909(4)
_cell_angle_alpha                90
_cell_angle_beta                 115.017(4)
_cell_angle_gamma                90
_cell_volume                     1703.47(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    7730
_cell_measurement_theta_min      2.05
_cell_measurement_theta_max      28.22

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_F_000             836
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.142
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.459
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            5729
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.047
_diffrn_reflns_theta_max         28.084
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.603
_diffrn_reflns_point_group_measured_fraction_full 0.659
_reflns_number_total             2498
_reflns_number_gt                2368
_reflns_threshold_expression     'I > 2σ(I)'

_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0320P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.010(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2498
_refine_ls_number_parameters     226
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0240
_refine_ls_wR_factor_ref         0.0552
_refine_ls_wR_factor_gt          0.0544
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.033
_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
C1 C -0.0101(3) 0.1463(2) 0.2613(5) 0.0257(7) Uani 1 1 d . . . . .
H1 H -0.0563 0.1122 0.1713 0.031 Uiso 1 1 calc R U . . .
C2 C -0.0357(3) 0.21729(19) 0.2237(5) 0.0298(7) Uani 1 1 d . . . . .
H2 H -0.0986 0.2318 0.1096 0.036 Uiso 1 1 calc R U . . .
C3 C 0.0318(3) 0.26661(17) 0.3548(5) 0.0284(7) Uani 1 1 d . . . . .
H3 H 0.0153 0.3155 0.3325 0.034 Uiso 1 1 calc R U . . .
C4 C 0.1232(4) 0.24427(15) 0.5184(6) 0.0260(7) Uani 1 1 d . . . . .
H4 H 0.1714 0.2775 0.6089 0.031 Uiso 1 1 calc R U . . .
C5 C 0.1439(3) 0.17223(16) 0.5488(4) 0.0214(7) Uani 1 1 d . . . . .
C6 C 0.2368(3) 0.14462(17) 0.7281(6) 0.0280(8) Uani 1 1 d . . . . .
H6A H 0.3082 0.1711 0.7564 0.034 Uiso 1 1 calc R U . . .
H6B H 0.2158 0.1513 0.8368 0.034 Uiso 1 1 calc R U . . .
C7 C 0.3482(3) 0.04173(16) 0.8295(4) 0.0194(6) Uani 1 1 d . . . . .
H7 H 0.4029 0.0731 0.9171 0.023 Uiso 1 1 calc R U . . .
C8 C 0.3778(3) -0.03191(15) 0.8484(5) 0.0192(6) Uani 1 1 d . . . . .
C9 C 0.3012(3) -0.08231(15) 0.7266(5) 0.0187(6) Uani 1 1 d . . . . .
C10 C 0.3273(3) -0.16013(15) 0.7316(4) 0.0192(6) Uani 1 1 d . . . . .
C11 C 0.2355(3) -0.20650(16) 0.6892(5) 0.0219(6) Uani 1 1 d . . . . .
H11 H 0.1623 -0.1883 0.6667 0.026 Uiso 1 1 calc R U . . .
C12 C 0.2503(3) -0.27902(16) 0.6797(5) 0.0264(7) Uani 1 1 d . . . . .
H12 H 0.1876 -0.3101 0.6528 0.032 Uiso 1 1 calc R U . . .
C13 C 0.3561(3) -0.30576(18) 0.7095(5) 0.0283(7) Uani 1 1 d . . . . .
H13 H 0.3666 -0.3552 0.7045 0.034 Uiso 1 1 calc R U . . .
C14 C 0.4465(3) -0.26016(17) 0.7467(5) 0.0274(7) Uani 1 1 d . . . . .
H14 H 0.5189 -0.2786 0.7652 0.033 Uiso 1 1 calc R U . . .
C15 C 0.4332(3) -0.18757(17) 0.7574(5) 0.0231(7) Uani 1 1 d . . . . .
H15 H 0.4960 -0.1568 0.7822 0.028 Uiso 1 1 calc R U . . .
C16 C 0.4853(3) -0.05075(17) 1.0126(5) 0.0210(6) Uani 1 1 d . . . . .
C17 C 0.6698(3) -0.00823(19) 1.2260(5) 0.0270(7) Uani 1 1 d . . . . .
H17A H 0.7162 -0.0419 1.1905 0.032 Uiso 1 1 calc R U . . .
H17B H 0.6579 -0.0282 1.3352 0.032 Uiso 1 1 calc R U . . .
C18 C 0.7297(3) 0.0619(2) 1.2806(6) 0.0350(8) Uani 1 1 d . . . . .
H18A H 0.7359 0.0827 1.1687 0.053 Uiso 1 1 calc R U . . .
H18B H 0.8064 0.0551 1.3835 0.053 Uiso 1 1 calc R U . . .
H18C H 0.6859 0.0936 1.3250 0.053 Uiso 1 1 calc R U . . .
Cl1 Cl 0.00423(6) -0.02642(4) 0.22668(10) 0.02319(16) Uani 1 1 d . . . . .
Cu1 Cu 0.12938(3) 0.02330(2) 0.50171(3) 0.01771(9) Uani 1 1 d . . . . .
N1 N 0.0786(2) 0.12427(13) 0.4222(4) 0.0194(5) Uani 1 1 d . . . . .
N2 N 0.2553(2) 0.06956(13) 0.7064(4) 0.0184(5) Uani 1 1 d . . . . .
O1 O 0.20319(19) -0.06710(11) 0.5957(3) 0.0219(5) Uani 1 1 d . . . . .
O2 O 0.5077(2) -0.10594(12) 1.0981(3) 0.0315(6) Uani 1 1 d . . . . .
O3 O 0.5611(2) 0.00385(12) 1.0647(3) 0.0248(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
C1 N1 1.348(4) . ?
C1 C2 1.386(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.380(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(4) . ?
C4 H4 0.9500 . ?
C5 N1 1.338(4) . ?
C5 C6 1.488(5) . ?
C6 N2 1.463(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.285(4) . ?
C7 C8 1.437(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.408(4) . ?
C8 C16 1.471(4) . ?
C9 O1 1.273(4) . ?
C9 C10 1.509(4) . ?
C10 C15 1.395(4) . ?
C10 C11 1.399(4) . ?
C11 C12 1.393(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 O2 1.203(4) . ?
C16 O3 1.363(4) . ?
C17 O3 1.445(4) . ?
C17 C18 1.505(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
Cl1 Cu1 2.2539(7) . ?
Cu1 N2 1.930(3) . ?
Cu1 O1 1.944(2) . ?
Cu1 N1 2.030(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
N1 C1 C2 121.8(3) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.8(3) . . ?
N1 C5 C6 116.7(3) . . ?
C4 C5 C6 121.5(3) . . ?
N2 C6 C5 110.0(3) . . ?
N2 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 126.7(3) . . ?
N2 C7 H7 116.6 . . ?
C8 C7 H7 116.6 . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 C16 123.3(3) . . ?
C7 C8 C16 115.8(3) . . ?
O1 C9 C8 123.8(3) . . ?
O1 C9 C10 112.2(3) . . ?
C8 C9 C10 124.0(3) . . ?
C15 C10 C11 118.8(3) . . ?
C15 C10 C9 124.2(3) . . ?
C11 C10 C9 116.7(3) . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 121.0(3) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C10 119.8(3) . . ?
C14 C15 H15 120.1 . . ?
C10 C15 H15 120.1 . . ?
O2 C16 O3 121.5(3) . . ?
O2 C16 C8 127.0(3) . . ?
O3 C16 C8 111.5(3) . . ?
O3 C17 C18 107.3(3) . . ?
O3 C17 H17A 110.3 . . ?
C18 C17 H17A 110.3 . . ?
O3 C17 H17B 110.3 . . ?
C18 C17 H17B 110.3 . . ?
H17A C17 H17B 108.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 Cu1 O1 89.16(10) . . ?
N2 Cu1 N1 82.60(10) . . ?
O1 Cu1 N1 170.63(10) . . ?
N2 Cu1 Cl1 167.78(8) . . ?
O1 Cu1 Cl1 91.43(7) . . ?
N1 Cu1 Cl1 95.68(8) . . ?
C5 N1 C1 119.2(3) . . ?
C5 N1 Cu1 113.4(2) . . ?
C1 N1 Cu1 127.5(2) . . ?
C7 N2 C6 117.5(3) . . ?
C7 N2 Cu1 128.0(2) . . ?
C6 N2 Cu1 114.4(2) . . ?
C9 O1 Cu1 131.32(19) . . ?
C16 O3 C17 116.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.1(5) . . . . ?
C1 C2 C3 C4 0.6(5) . . . . ?
C2 C3 C4 C5 -1.2(6) . . . . ?
C3 C4 C5 N1 1.2(6) . . . . ?
C3 C4 C5 C6 -176.2(4) . . . . ?
N1 C5 C6 N2 14.3(5) . . . . ?
C4 C5 C6 N2 -168.2(3) . . . . ?
N2 C7 C8 C9 -1.0(5) . . . . ?
N2 C7 C8 C16 -174.7(3) . . . . ?
C7 C8 C9 O1 -0.3(5) . . . . ?
C16 C8 C9 O1 173.0(3) . . . . ?
C7 C8 C9 C10 177.5(3) . . . . ?
C16 C8 C9 C10 -9.2(5) . . . . ?
O1 C9 C10 C15 138.2(3) . . . . ?
C8 C9 C10 C15 -39.9(5) . . . . ?
O1 C9 C10 C11 -35.6(4) . . . . ?
C8 C9 C10 C11 146.4(3) . . . . ?
C15 C10 C11 C12 2.3(5) . . . . ?
C9 C10 C11 C12 176.4(3) . . . . ?
C10 C11 C12 C13 -0.9(5) . . . . ?
C11 C12 C13 C14 -0.7(5) . . . . ?
C12 C13 C14 C15 0.9(6) . . . . ?
C13 C14 C15 C10 0.4(5) . . . . ?
C11 C10 C15 C14 -2.0(5) . . . . ?
C9 C10 C15 C14 -175.6(3) . . . . ?
C9 C8 C16 O2 -22.6(5) . . . . ?
C7 C8 C16 O2 150.9(3) . . . . ?
C9 C8 C16 O3 158.5(3) . . . . ?
C7 C8 C16 O3 -27.9(4) . . . . ?
C4 C5 N1 C1 -0.4(5) . . . . ?
C6 C5 N1 C1 177.0(3) . . . . ?
C4 C5 N1 Cu1 179.3(3) . . . . ?
C6 C5 N1 Cu1 -3.2(4) . . . . ?
C2 C1 N1 C5 -0.2(5) . . . . ?
C2 C1 N1 Cu1 -179.9(3) . . . . ?
C8 C7 N2 C6 172.5(3) . . . . ?
C8 C7 N2 Cu1 -2.9(5) . . . . ?
C5 C6 N2 C7 164.7(3) . . . . ?
C5 C6 N2 Cu1 -19.2(4) . . . . ?
C8 C9 O1 Cu1 5.5(5) . . . . ?
C10 C9 O1 Cu1 -172.5(2) . . . . ?
O2 C16 O3 C17 0.5(5) . . . . ?
C8 C16 O3 C17 179.5(3) . . . . ?
C18 C17 O3 C16 -169.5(3) . . . . ?

_refine_diff_density_max         0.333
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_cl112
_database_code_depnum_ccdc_archive 'CCDC 1566640'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;
_chemical_name_common            '[CuL30b]2SO4'
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H30 Cu2 N4 O9 S, C H4 O'
_chemical_formula_sum            'C26 H34 Cu2 N4 O10 S'
_chemical_formula_weight         721.71

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'
S S 0.1246 0.1234 '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                   12.7600(18)
_cell_length_b                   16.897(3)
_cell_length_c                   13.781(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.639(11)
_cell_angle_gamma                90
_cell_volume                     2899.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    9449
_cell_measurement_theta_min      1.76
_cell_measurement_theta_max      26.00

_exptl_crystal_description       block
_exptl_crystal_colour            'blue green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.114
_exptl_absorpt_coefficient_mu    1.603
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            19204
_diffrn_reflns_av_unetI/netI     0.0794
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.935
_diffrn_reflns_theta_max         28.561
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             6861
_reflns_number_gt                4686
_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0561P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6861
_refine_ls_number_parameters     390
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1117
_refine_ls_wR_factor_gt          0.1030
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_restrained_S_all      0.909
_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
C11 C -0.2622(3) 0.0474(2) 0.6324(3) 0.0249(8) Uani 1 1 d . . . . .
H11 H -0.2534 0.1032 0.6305 0.030 Uiso 1 1 calc R U . . .
C12 C -0.3597(3) 0.0169(3) 0.6393(3) 0.0317(9) Uani 1 1 d . . . . .
H12 H -0.4184 0.0511 0.6407 0.038 Uiso 1 1 calc R U . . .
C13 C -0.3721(3) -0.0644(3) 0.6440(3) 0.0363(10) Uani 1 1 d . . . . .
H13 H -0.4394 -0.0862 0.6488 0.044 Uiso 1 1 calc R U . . .
C14 C -0.2861(3) -0.1134(2) 0.6418(3) 0.0295(9) Uani 1 1 d . . . . .
H14 H -0.2924 -0.1692 0.6468 0.035 Uiso 1 1 calc R U . . .
C15 C -0.1898(3) -0.0789(2) 0.6320(3) 0.0219(7) Uani 1 1 d . . . . .
C16 C -0.0964(3) -0.1280(2) 0.6197(3) 0.0257(8) Uani 1 1 d . . . . .
H16A H -0.0781 -0.1665 0.6750 0.031 Uiso 1 1 calc R U . . .
H16B H -0.1153 -0.1579 0.5565 0.031 Uiso 1 1 calc R U . . .
C17 C 0.0851(3) -0.1115(2) 0.6135(3) 0.0232(7) Uani 1 1 d . . . . .
H17 H 0.0837 -0.1677 0.6099 0.028 Uiso 1 1 calc R U . . .
C18 C 0.1849(3) -0.0742(2) 0.6123(3) 0.0252(8) Uani 1 1 d . . . . .
C19 C 0.1948(3) 0.0085(2) 0.6156(3) 0.0232(8) Uani 1 1 d . . . . .
C20 C 0.2976(3) 0.0510(3) 0.6124(3) 0.0292(9) Uani 1 1 d . . . . .
H20A H 0.2832 0.1078 0.6023 0.044 Uiso 1 1 calc R U . . .
H20B H 0.3269 0.0302 0.5575 0.044 Uiso 1 1 calc R U . . .
H20C H 0.3497 0.0429 0.6753 0.044 Uiso 1 1 calc R U . . .
C21 C 0.2774(4) -0.1265(3) 0.6088(3) 0.0349(10) Uani 1 1 d . . . . .
C22 C 0.2557(4) -0.2133(3) 0.5890(5) 0.068(2) Uani 1 1 d . . . . .
H22A H 0.3194 -0.2384 0.5735 0.102 Uiso 1 1 calc R U . . .
H22B H 0.1946 -0.2196 0.5325 0.102 Uiso 1 1 calc R U . . .
H22C H 0.2392 -0.2383 0.6480 0.102 Uiso 1 1 calc R U . . .
C31 C -0.0665(3) 0.1061(2) 0.8502(3) 0.0209(7) Uani 1 1 d . . . . .
H31 H -0.0775 0.1610 0.8372 0.025 Uiso 1 1 calc R U . . .
C32 C -0.1489(3) 0.0616(2) 0.8724(3) 0.0237(8) Uani 1 1 d . . . . .
H32 H -0.2157 0.0854 0.8750 0.028 Uiso 1 1 calc R U . . .
C33 C -0.1318(3) -0.0189(2) 0.8909(3) 0.0273(8) Uani 1 1 d . . . . .
H33 H -0.1874 -0.0509 0.9057 0.033 Uiso 1 1 calc R U . . .
C34 C -0.0346(3) -0.0518(2) 0.8876(3) 0.0254(8) Uani 1 1 d . . . . .
H34 H -0.0221 -0.1067 0.8996 0.031 Uiso 1 1 calc R U . . .
C35 C 0.0458(3) -0.0031(2) 0.8665(2) 0.0194(7) Uani 1 1 d . . . . .
C36 C 0.1565(3) -0.0340(2) 0.8661(3) 0.0231(7) Uani 1 1 d . . . . .
H36A H 0.1853 -0.0631 0.9286 0.028 Uiso 1 1 calc R U . . .
H36B H 0.1527 -0.0712 0.8098 0.028 Uiso 1 1 calc R U . . .
C37 C 0.3291(3) 0.0190(2) 0.8693(3) 0.0263(8) Uani 1 1 d . . . . .
H37 H 0.3523 -0.0338 0.8851 0.032 Uiso 1 1 calc R U . . .
C38 C 0.4100(3) 0.0759(3) 0.8620(3) 0.0280(8) Uani 1 1 d . . . . .
C39 C 0.3841(3) 0.1544(2) 0.8318(3) 0.0267(8) Uani 1 1 d . . . . .
C40 C 0.4669(3) 0.2136(3) 0.8163(4) 0.0434(11) Uani 1 1 d . . . . .
H40A H 0.4354 0.2487 0.7610 0.065 Uiso 1 1 calc R U . . .
H40B H 0.5285 0.1857 0.8008 0.065 Uiso 1 1 calc R U . . .
H40C H 0.4905 0.2449 0.8770 0.065 Uiso 1 1 calc R U . . .
C41 C 0.5225(3) 0.0471(3) 0.8826(3) 0.0397(11) Uani 1 1 d . . . . .
C42 C 0.5417(4) -0.0400(3) 0.8709(3) 0.0451(12) Uani 1 1 d . . . . .
H42A H 0.6105 -0.0476 0.8516 0.068 Uiso 1 1 calc R U . . .
H42B H 0.4836 -0.0620 0.8195 0.068 Uiso 1 1 calc R U . . .
H42C H 0.5434 -0.0670 0.9342 0.068 Uiso 1 1 calc R U . . .
C61 C 0.2735(4) 0.2141(3) 1.0459(3) 0.0362(9) Uani 1 1 d . . . . .
H61A H 0.3336 0.1825 1.0333 0.054 Uiso 1 1 calc R U . . .
H61B H 0.2691 0.2084 1.1156 0.054 Uiso 1 1 calc R U . . .
H61C H 0.2851 0.2699 1.0318 0.054 Uiso 1 1 calc R U . . .
C71 C 0.3623(8) -0.2142(6) 0.8679(6) 0.116(4) Uani 1 1 d . . . . .
H71A H 0.3205 -0.1717 0.8896 0.174 Uiso 1 1 calc R U . . .
H71B H 0.4034 -0.1929 0.8215 0.174 Uiso 1 1 calc R U . . .
H71C H 0.4118 -0.2368 0.9258 0.174 Uiso 1 1 calc R U . . .
N11 N -0.1781(2) -0.00029(18) 0.6283(2) 0.0199(6) Uani 1 1 d . . . . .
N12 N -0.0038(2) -0.07678(17) 0.6190(2) 0.0200(6) Uani 1 1 d . . . . .
N31 N 0.0292(2) 0.07388(17) 0.8466(2) 0.0189(6) Uani 1 1 d . . . . .
N32 N 0.2278(2) 0.03245(18) 0.8564(2) 0.0203(6) Uani 1 1 d . . . . .
O11 O 0.11648(19) 0.05605(15) 0.61985(18) 0.0215(5) Uani 1 1 d . . . . .
O12 O 0.3684(3) -0.1022(2) 0.6217(3) 0.0547(10) Uani 1 1 d . . . . .
O31 O 0.28914(19) 0.18175(16) 0.81164(19) 0.0242(5) Uani 1 1 d . . . . .
O32 O 0.6000(2) 0.0904(3) 0.9081(3) 0.0587(11) Uani 1 1 d . . . . .
O51 O -0.06905(19) 0.14328(14) 0.63197(19) 0.0200(5) Uani 1 1 d . . . . .
O52 O 0.0778(2) 0.21563(14) 0.7371(2) 0.0244(5) Uani 1 1 d . . . . .
O53 O -0.0900(2) 0.27777(16) 0.6735(2) 0.0330(7) Uani 1 1 d . . . . .
O54 O 0.0244(3) 0.24428(19) 0.5624(2) 0.0377(7) Uani 1 1 d . . . . .
O60 O 0.1762(2) 0.18754(17) 0.9833(2) 0.0291(6) Uani 1 1 d . . . . .
H60 H 0.1238 0.2059 1.0039 0.035 Uiso 1 1 calc R U . . .
O70 O 0.2962(4) -0.2703(3) 0.8228(4) 0.0836(15) Uani 1 1 d . . . . .
H70 H 0.2344 -0.2624 0.8327 0.125 Uiso 1 1 calc R U . . .
S50 S -0.01332(6) 0.22133(5) 0.65019(6) 0.01602(17) Uani 1 1 d . . . . .
Cu1 Cu -0.02950(3) 0.03385(2) 0.62310(3) 0.01575(10) Uani 1 1 d . . . . .
Cu2 Cu 0.15594(3) 0.13130(2) 0.81959(3) 0.01737(11) 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
C11 N11 1.354(5) . ?
C11 C12 1.369(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(5) . ?
C14 H14 0.9500 . ?
C15 N11 1.339(5) . ?
C15 C16 1.491(5) . ?
C16 N12 1.466(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 N12 1.295(4) . ?
C17 C18 1.424(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.402(5) . ?
C18 C21 1.484(5) . ?
C19 O11 1.294(4) . ?
C19 C20 1.505(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 O12 1.208(6) . ?
C21 C22 1.505(7) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C31 N31 1.347(4) . ?
C31 C32 1.380(5) . ?
C31 H31 0.9500 . ?
C32 C33 1.392(6) . ?
C32 H32 0.9500 . ?
C33 C34 1.369(6) . ?
C33 H33 0.9500 . ?
C34 C35 1.394(5) . ?
C34 H34 0.9500 . ?
C35 N31 1.337(4) . ?
C35 C36 1.506(5) . ?
C36 N32 1.470(5) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 N32 1.285(5) . ?
C37 C38 1.431(6) . ?
C37 H37 0.9500 . ?
C38 C39 1.407(6) . ?
C38 C41 1.482(5) . ?
C39 O31 1.270(4) . ?
C39 C40 1.504(6) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 O32 1.219(6) . ?
C41 C42 1.506(7) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C61 O60 1.421(5) . ?
C61 H61A 0.9800 . ?
C61 H61B 0.9800 . ?
C61 H61C 0.9800 . ?
C71 O70 1.328(8) . ?
C71 H71A 0.9800 . ?
C71 H71B 0.9800 . ?
C71 H71C 0.9800 . ?
N11 Cu1 1.998(3) . ?
N12 Cu1 1.901(3) . ?
N31 Cu2 1.990(3) . ?
N32 Cu2 1.919(3) . ?
O11 Cu1 1.910(2) . ?
O31 Cu2 1.926(2) . ?
O51 S50 1.493(2) . ?
O51 Cu1 1.927(2) . ?
O52 S50 1.478(3) . ?
O52 Cu2 1.955(3) . ?
O53 S50 1.452(3) . ?
O54 S50 1.449(3) . ?
O60 Cu2 2.410(3) . ?
O60 H60 0.8400 . ?
O70 H70 0.8400 . ?

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
N11 C11 C12 121.3(4) . . ?
N11 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C13 119.5(4) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 119.6(4) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 118.2(4) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
N11 C15 C14 121.8(4) . . ?
N11 C15 C16 116.6(3) . . ?
C14 C15 C16 121.5(3) . . ?
N12 C16 C15 109.8(3) . . ?
N12 C16 H16A 109.7 . . ?
C15 C16 H16A 109.7 . . ?
N12 C16 H16B 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
N12 C17 C18 126.6(3) . . ?
N12 C17 H17 116.7 . . ?
C18 C17 H17 116.7 . . ?
C19 C18 C17 121.1(3) . . ?
C19 C18 C21 121.9(4) . . ?
C17 C18 C21 117.1(4) . . ?
O11 C19 C18 123.7(3) . . ?
O11 C19 C20 113.1(3) . . ?
C18 C19 C20 123.2(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O12 C21 C18 122.5(4) . . ?
O12 C21 C22 119.4(4) . . ?
C18 C21 C22 118.1(4) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N31 C31 C32 121.9(3) . . ?
N31 C31 H31 119.0 . . ?
C32 C31 H31 119.0 . . ?
C31 C32 C33 118.4(3) . . ?
C31 C32 H32 120.8 . . ?
C33 C32 H32 120.8 . . ?
C34 C33 C32 119.8(3) . . ?
C34 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
C33 C34 C35 118.7(3) . . ?
C33 C34 H34 120.6 . . ?
C35 C34 H34 120.6 . . ?
N31 C35 C34 121.7(3) . . ?
N31 C35 C36 116.4(3) . . ?
C34 C35 C36 122.0(3) . . ?
N32 C36 C35 109.5(3) . . ?
N32 C36 H36A 109.8 . . ?
C35 C36 H36A 109.8 . . ?
N32 C36 H36B 109.8 . . ?
C35 C36 H36B 109.8 . . ?
H36A C36 H36B 108.2 . . ?
N32 C37 C38 126.2(4) . . ?
N32 C37 H37 116.9 . . ?
C38 C37 H37 116.9 . . ?
C39 C38 C37 121.8(3) . . ?
C39 C38 C41 121.4(4) . . ?
C37 C38 C41 116.7(4) . . ?
O31 C39 C38 124.0(4) . . ?
O31 C39 C40 113.1(4) . . ?
C38 C39 C40 122.8(4) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
O32 C41 C38 123.3(5) . . ?
O32 C41 C42 118.4(4) . . ?
C38 C41 C42 118.3(4) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
O60 C61 H61A 109.5 . . ?
O60 C61 H61B 109.5 . . ?
H61A C61 H61B 109.5 . . ?
O60 C61 H61C 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
O70 C71 H71A 109.5 . . ?
O70 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
O70 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
C15 N11 C11 119.5(3) . . ?
C15 N11 Cu1 113.8(2) . . ?
C11 N11 Cu1 126.7(3) . . ?
C17 N12 C16 116.8(3) . . ?
C17 N12 Cu1 127.4(3) . . ?
C16 N12 Cu1 115.8(2) . . ?
C35 N31 C31 119.4(3) . . ?
C35 N31 Cu2 114.4(2) . . ?
C31 N31 Cu2 126.2(2) . . ?
C37 N32 C36 118.4(3) . . ?
C37 N32 Cu2 126.7(3) . . ?
C36 N32 Cu2 114.8(2) . . ?
C19 O11 Cu1 130.3(2) . . ?
C39 O31 Cu2 129.6(3) . . ?
S50 O51 Cu1 137.41(15) . . ?
S50 O52 Cu2 136.82(16) . . ?
C61 O60 Cu2 126.4(2) . . ?
C61 O60 H60 109.5 . . ?
Cu2 O60 H60 122.0 . . ?
C71 O70 H70 109.5 . . ?
O54 S50 O53 111.82(19) . . ?
O54 S50 O52 110.36(17) . . ?
O53 S50 O52 108.20(16) . . ?
O54 S50 O51 109.20(16) . . ?
O53 S50 O51 107.34(15) . . ?
O52 S50 O51 109.87(14) . . ?
N12 Cu1 O11 90.98(12) . . ?
N12 Cu1 O51 173.97(11) . . ?
O11 Cu1 O51 94.78(10) . . ?
N12 Cu1 N11 83.58(13) . . ?
O11 Cu1 N11 174.49(12) . . ?
O51 Cu1 N11 90.63(11) . . ?
N32 Cu2 O31 91.35(12) . . ?
N32 Cu2 O52 160.29(12) . . ?
O31 Cu2 O52 89.36(11) . . ?
N32 Cu2 N31 83.52(12) . . ?
O31 Cu2 N31 171.92(12) . . ?
O52 Cu2 N31 97.58(11) . . ?
N32 Cu2 O60 98.54(11) . . ?
O31 Cu2 O60 87.90(10) . . ?
O52 Cu2 O60 101.17(10) . . ?
N31 Cu2 O60 86.69(10) . . ?

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
N11 C11 C12 C13 1.2(6) . . . . ?
C11 C12 C13 C14 0.0(6) . . . . ?
C12 C13 C14 C15 -1.7(6) . . . . ?
C13 C14 C15 N11 2.4(6) . . . . ?
C13 C14 C15 C16 -174.3(4) . . . . ?
N11 C15 C16 N12 7.5(5) . . . . ?
C14 C15 C16 N12 -175.6(3) . . . . ?
N12 C17 C18 C19 -1.1(6) . . . . ?
N12 C17 C18 C21 178.1(4) . . . . ?
C17 C18 C19 O11 -0.1(6) . . . . ?
C21 C18 C19 O11 -179.2(3) . . . . ?
C17 C18 C19 C20 -178.7(3) . . . . ?
C21 C18 C19 C20 2.2(6) . . . . ?
C19 C18 C21 O12 9.9(6) . . . . ?
C17 C18 C21 O12 -169.3(4) . . . . ?
C19 C18 C21 C22 -170.4(4) . . . . ?
C17 C18 C21 C22 10.4(6) . . . . ?
N31 C31 C32 C33 -0.3(5) . . . . ?
C31 C32 C33 C34 0.6(5) . . . . ?
C32 C33 C34 C35 0.5(5) . . . . ?
C33 C34 C35 N31 -2.0(5) . . . . ?
C33 C34 C35 C36 177.2(3) . . . . ?
N31 C35 C36 N32 7.7(4) . . . . ?
C34 C35 C36 N32 -171.5(3) . . . . ?
N32 C37 C38 C39 -4.8(6) . . . . ?
N32 C37 C38 C41 178.4(4) . . . . ?
C37 C38 C39 O31 2.1(6) . . . . ?
C41 C38 C39 O31 178.8(3) . . . . ?
C37 C38 C39 C40 -175.3(4) . . . . ?
C41 C38 C39 C40 1.3(6) . . . . ?
C39 C38 C41 O32 25.7(6) . . . . ?
C37 C38 C41 O32 -157.5(4) . . . . ?
C39 C38 C41 C42 -153.9(4) . . . . ?
C37 C38 C41 C42 22.8(5) . . . . ?
C14 C15 N11 C11 -1.2(5) . . . . ?
C16 C15 N11 C11 175.6(3) . . . . ?
C14 C15 N11 Cu1 176.2(3) . . . . ?
C16 C15 N11 Cu1 -6.9(4) . . . . ?
C12 C11 N11 C15 -0.6(5) . . . . ?
C12 C11 N11 Cu1 -177.7(3) . . . . ?
C18 C17 N12 C16 -179.7(3) . . . . ?
C18 C17 N12 Cu1 2.1(5) . . . . ?
C15 C16 N12 C17 176.9(3) . . . . ?
C15 C16 N12 Cu1 -4.7(4) . . . . ?
C34 C35 N31 C31 2.3(5) . . . . ?
C36 C35 N31 C31 -177.0(3) . . . . ?
C34 C35 N31 Cu2 179.6(3) . . . . ?
C36 C35 N31 Cu2 0.4(4) . . . . ?
C32 C31 N31 C35 -1.1(5) . . . . ?
C32 C31 N31 Cu2 -178.1(3) . . . . ?
C38 C37 N32 C36 179.5(3) . . . . ?
C38 C37 N32 Cu2 2.2(5) . . . . ?
C35 C36 N32 C37 169.9(3) . . . . ?
C35 C36 N32 Cu2 -12.5(3) . . . . ?
C18 C19 O11 Cu1 0.1(5) . . . . ?
C20 C19 O11 Cu1 178.8(2) . . . . ?
C38 C39 O31 Cu2 2.7(5) . . . . ?
C40 C39 O31 Cu2 -179.6(3) . . . . ?
Cu2 O52 S50 O54 -108.8(3) . . . . ?
Cu2 O52 S50 O53 128.6(2) . . . . ?
Cu2 O52 S50 O51 11.7(3) . . . . ?
Cu1 O51 S50 O54 73.9(3) . . . . ?
Cu1 O51 S50 O53 -164.7(2) . . . . ?
Cu1 O51 S50 O52 -47.3(3) . . . . ?

_refine_diff_density_max         1.433
_refine_diff_density_min         -0.839
_refine_diff_density_rms         0.110

####################################################################### 
# 
# 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_cl098
_database_code_depnum_ccdc_archive 'CCDC 1566638'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_date             2017-08-03
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;
_chemical_name_common            '[CuL30aN3]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H30 Cu2 N10 O6'
_chemical_formula_sum            'C26 H30 Cu2 N10 O6'
_chemical_formula_weight         705.68

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'
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                   20.5772(11)
_cell_length_b                   19.5249(15)
_cell_length_c                   7.1596(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.083(4)
_cell_angle_gamma                90
_cell_volume                     2869.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    7370
_cell_measurement_theta_min      1.99
_cell_measurement_theta_max      28.36

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_F_000             1448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.145
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.068
_exptl_absorpt_coefficient_mu    1.543
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            9743
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.439
_diffrn_reflns_theta_max         28.441
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3420
_reflns_number_gt                2680
_reflns_threshold_expression     'I > 2σ(I)'

_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0282P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3420
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0609
_refine_ls_wR_factor_gt          0.0577
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_restrained_S_all      0.937
_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
C1 C 0.37387(8) 0.16253(10) 0.1394(2) 0.0200(4) Uani 1 1 d . . . . .
H1 H 0.3861 0.2064 0.0962 0.024 Uiso 1 1 calc R U . . .
C2 C 0.41648(9) 0.10803(10) 0.1274(2) 0.0213(4) Uani 1 1 d . . . . .
H2 H 0.4579 0.1144 0.0792 0.026 Uiso 1 1 calc R U . . .
C3 C 0.39748(9) 0.04416(10) 0.1871(2) 0.0220(4) Uani 1 1 d . . . . .
H3 H 0.4256 0.0059 0.1777 0.026 Uiso 1 1 calc R U . . .
C4 C 0.33737(9) 0.03599(10) 0.2607(2) 0.0203(4) Uani 1 1 d . . . . .
H4 H 0.3238 -0.0076 0.3025 0.024 Uiso 1 1 calc R U . . .
C5 C 0.29757(8) 0.09312(10) 0.2717(2) 0.0177(3) Uani 1 1 d . . . . .
C6 C 0.23295(9) 0.08891(10) 0.3567(3) 0.0229(4) Uani 1 1 d . . . . .
H6A H 0.2050 0.0545 0.2886 0.028 Uiso 1 1 calc R U . . .
H6B H 0.2396 0.0744 0.4892 0.028 Uiso 1 1 calc R U . . .
C7 C 0.14375(8) 0.16197(10) 0.4103(2) 0.0190(4) Uani 1 1 d . . . . .
H7 H 0.1253 0.1219 0.4597 0.023 Uiso 1 1 calc R U . . .
C8 C 0.10625(8) 0.22362(10) 0.4133(2) 0.0181(3) Uani 1 1 d . . . . .
C9 C 0.13064(8) 0.28734(10) 0.3591(2) 0.0188(4) Uani 1 1 d . . . . .
C10 C 0.09291(9) 0.35299(10) 0.3621(3) 0.0231(4) Uani 1 1 d . . . . .
H10A H 0.1202 0.3909 0.3234 0.035 Uiso 1 1 calc R U . . .
H10B H 0.0800 0.3615 0.4892 0.035 Uiso 1 1 calc R U . . .
H10C H 0.0539 0.3495 0.2758 0.035 Uiso 1 1 calc R U . . .
C11 C 0.03869(8) 0.21832(10) 0.4681(2) 0.0210(4) Uani 1 1 d . . . . .
C12 C -0.04813(9) 0.14287(12) 0.5257(3) 0.0277(4) Uani 1 1 d . . . . .
H12A H -0.0775 0.1718 0.4432 0.033 Uiso 1 1 calc R U . . .
H12B H -0.0535 0.1557 0.6574 0.033 Uiso 1 1 calc R U . . .
C13 C -0.06382(12) 0.06828(14) 0.4945(5) 0.0583(8) Uani 1 1 d . . . . .
H13A H -0.0552 0.0555 0.3662 0.087 Uiso 1 1 calc R U . . .
H13B H -0.1099 0.0602 0.5140 0.087 Uiso 1 1 calc R U . . .
H13C H -0.0366 0.0405 0.5832 0.087 Uiso 1 1 calc R U . . .
N1 N 0.31536(7) 0.15485(8) 0.21103(19) 0.0173(3) Uani 1 1 d . . . . .
N2 N 0.20100(7) 0.15621(8) 0.3457(2) 0.0184(3) Uani 1 1 d . . . . .
N3 N 0.29939(7) 0.29866(8) 0.1080(2) 0.0212(3) Uani 1 1 d . . . . .
N4 N 0.28889(7) 0.35817(9) 0.1372(2) 0.0208(3) Uani 1 1 d . . . . .
N5 N 0.27991(9) 0.41578(9) 0.1590(3) 0.0327(4) Uani 1 1 d . . . . .
O1 O 0.18725(6) 0.29514(7) 0.29898(18) 0.0229(3) Uani 1 1 d . . . . .
O2 O 0.00236(6) 0.26551(8) 0.49512(19) 0.0303(3) Uani 1 1 d . . . . .
O3 O 0.01912(6) 0.15232(8) 0.48168(19) 0.0253(3) Uani 1 1 d . . . . .
Cu1 Cu 0.24857(2) 0.22787(2) 0.23011(3) 0.01755(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
C1 N1 1.350(2) . ?
C1 C2 1.385(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.384(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.341(2) . ?
C5 C6 1.503(2) . ?
C6 N2 1.469(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.301(2) . ?
C7 C8 1.431(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.407(3) . ?
C8 C11 1.475(2) . ?
C9 O1 1.279(2) . ?
C9 C10 1.500(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O2 1.211(2) . ?
C11 O3 1.355(2) . ?
C12 O3 1.453(2) . ?
C12 C13 1.505(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N1 Cu1 1.9917(15) . ?
N2 Cu1 1.9278(16) . ?
N3 N4 1.203(2) . ?
N3 Cu1 1.9743(16) . ?
N4 N5 1.152(2) . ?
O1 Cu1 1.9102(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 121.57(18) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C3 C2 C1 118.64(17) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 120.00(18) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 118.31(18) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C4 121.83(16) . . ?
N1 C5 C6 116.75(16) . . ?
C4 C5 C6 121.40(17) . . ?
N2 C6 C5 109.57(15) . . ?
N2 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
N2 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 125.52(18) . . ?
N2 C7 H7 117.2 . . ?
C8 C7 H7 117.2 . . ?
C9 C8 C7 122.46(16) . . ?
C9 C8 C11 119.81(16) . . ?
C7 C8 C11 117.68(17) . . ?
O1 C9 C8 123.33(16) . . ?
O1 C9 C10 112.84(16) . . ?
C8 C9 C10 123.83(16) . . ?
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 . . ?
O2 C11 O3 121.48(16) . . ?
O2 C11 C8 126.40(19) . . ?
O3 C11 C8 112.09(16) . . ?
O3 C12 C13 106.77(17) . . ?
O3 C12 H12A 110.4 . . ?
C13 C12 H12A 110.4 . . ?
O3 C12 H12B 110.4 . . ?
C13 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 N1 C1 119.63(16) . . ?
C5 N1 Cu1 114.55(12) . . ?
C1 N1 Cu1 125.79(13) . . ?
C7 N2 C6 118.14(16) . . ?
C7 N2 Cu1 126.18(14) . . ?
C6 N2 Cu1 115.67(11) . . ?
N4 N3 Cu1 119.47(12) . . ?
N5 N4 N3 177.4(2) . . ?
C9 O1 Cu1 129.72(12) . . ?
C11 O3 C12 115.38(15) . . ?
O1 Cu1 N2 91.33(6) . . ?
O1 Cu1 N3 90.77(6) . . ?
N2 Cu1 N3 177.88(7) . . ?
O1 Cu1 N1 168.99(6) . . ?
N2 Cu1 N1 83.33(6) . . ?
N3 Cu1 N1 94.64(6) . . ?

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
N1 C1 C2 C3 1.4(3) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 N1 1.0(3) . . . . ?
C3 C4 C5 C6 -177.56(16) . . . . ?
N1 C5 C6 N2 2.6(2) . . . . ?
C4 C5 C6 N2 -178.71(16) . . . . ?
N2 C7 C8 C9 -5.6(3) . . . . ?
N2 C7 C8 C11 171.81(16) . . . . ?
C7 C8 C9 O1 1.7(3) . . . . ?
C11 C8 C9 O1 -175.62(15) . . . . ?
C7 C8 C9 C10 -179.41(15) . . . . ?
C11 C8 C9 C10 3.3(2) . . . . ?
C9 C8 C11 O2 -10.0(3) . . . . ?
C7 C8 C11 O2 172.56(17) . . . . ?
C9 C8 C11 O3 168.31(14) . . . . ?
C7 C8 C11 O3 -9.1(2) . . . . ?
C4 C5 N1 C1 -1.0(2) . . . . ?
C6 C5 N1 C1 177.66(15) . . . . ?
C4 C5 N1 Cu1 177.20(13) . . . . ?
C6 C5 N1 Cu1 -4.2(2) . . . . ?
C2 C1 N1 C5 -0.2(3) . . . . ?
C2 C1 N1 Cu1 -178.20(13) . . . . ?
C8 C7 N2 C6 179.05(16) . . . . ?
C8 C7 N2 Cu1 -2.3(3) . . . . ?
C5 C6 N2 C7 178.94(15) . . . . ?
C5 C6 N2 Cu1 0.16(19) . . . . ?
C8 C9 O1 Cu1 10.1(2) . . . . ?
C10 C9 O1 Cu1 -168.95(11) . . . . ?
O2 C11 O3 C12 1.5(2) . . . . ?
C8 C11 O3 C12 -176.92(14) . . . . ?
C13 C12 O3 C11 168.39(19) . . . . ?

_refine_diff_density_max         0.316
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_cl108
_database_code_depnum_ccdc_archive 'CCDC 1566622'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;
_chemical_name_common            '[CuL30fNO3]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H34 Cu2 N6 O12'
_chemical_formula_sum            'C36 H34 Cu2 N6 O12'
_chemical_formula_weight         869.76

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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   10.2653(4)
_cell_length_b                   8.8823(4)
_cell_length_c                   20.2634(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.713(3)
_cell_angle_gamma                90
_cell_volume                     1830.89(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    9119
_cell_measurement_theta_min      2.03
_cell_measurement_theta_max      28.45

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_F_000             892
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.163
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.134
_exptl_absorpt_coefficient_mu    1.235
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            13069
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.028
_diffrn_reflns_theta_max         28.489
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             4324
_reflns_number_gt                3240
_reflns_threshold_expression     'I > 2σ(I)'


_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0356P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4324
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0726
_refine_ls_wR_factor_gt          0.0687
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_restrained_S_all      0.913
_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 0.07238(2) 0.32960(3) 0.48341(2) 0.02698(8) Uani 1 1 d . . . . .
O3 O 0.48538(13) 0.24615(18) 0.35096(7) 0.0327(3) Uani 1 1 d . . . . .
O2 O 0.56782(14) 0.14667(19) 0.44920(8) 0.0397(4) Uani 1 1 d . . . . .
O11 O -0.08160(13) 0.45231(17) 0.44622(7) 0.0299(3) Uani 1 1 d . . . . .
O12 O -0.07520(16) 0.3502(2) 0.34879(8) 0.0445(4) Uani 1 1 d . . . . .
O1 O 0.17735(13) 0.43524(16) 0.42773(7) 0.0311(3) Uani 1 1 d . . . . .
C15 C 0.25311(19) 0.5744(2) 0.31620(10) 0.0281(4) Uani 1 1 d . . . . .
H15 H 0.1645 0.5408 0.3096 0.034 Uiso 1 1 calc R U . . .
N1 N -0.02857(16) 0.20357(18) 0.53894(8) 0.0266(4) Uani 1 1 d . . . . .
O13 O -0.17661(19) 0.5604(2) 0.35719(9) 0.0566(5) Uani 1 1 d . . . . .
N2 N 0.21555(15) 0.20249(19) 0.51816(8) 0.0266(4) Uani 1 1 d . . . . .
C10 C 0.34142(18) 0.5127(2) 0.36770(10) 0.0267(4) Uani 1 1 d . . . . .
C8 C 0.36378(18) 0.2760(2) 0.44044(9) 0.0257(4) Uani 1 1 d . . . . .
C9 C 0.29136(18) 0.4007(2) 0.41305(9) 0.0261(4) Uani 1 1 d . . . . .
C16 C 0.48287(18) 0.2185(2) 0.41541(10) 0.0287(4) Uani 1 1 d . . . . .
C2 C -0.2189(2) 0.1214(3) 0.58422(11) 0.0336(5) Uani 1 1 d . . . . .
H2 H -0.3106 0.1298 0.5860 0.040 Uiso 1 1 calc R U . . .
N11 N -0.11184(16) 0.4541(2) 0.38123(9) 0.0317(4) Uani 1 1 d . . . . .
C11 C 0.4695(2) 0.5662(3) 0.37773(12) 0.0358(5) Uani 1 1 d . . . . .
H11 H 0.5300 0.5275 0.4133 0.043 Uiso 1 1 calc R U . . .
C5 C 0.04452(19) 0.1020(2) 0.57710(9) 0.0270(4) Uani 1 1 d . . . . .
C1 C -0.1585(2) 0.2126(2) 0.54283(10) 0.0299(4) Uani 1 1 d . . . . .
H1 H -0.2099 0.2844 0.5161 0.036 Uiso 1 1 calc R U . . .
C4 C -0.0107(2) 0.0060(2) 0.61917(10) 0.0325(5) Uani 1 1 d . . . . .
H4 H 0.0419 -0.0666 0.6449 0.039 Uiso 1 1 calc R U . . .
C7 C 0.32529(18) 0.1897(2) 0.49341(9) 0.0266(4) Uani 1 1 d . . . . .
H7 H 0.3855 0.1155 0.5126 0.032 Uiso 1 1 calc R U . . .
C17 C 0.6051(2) 0.2040(3) 0.32445(12) 0.0419(6) Uani 1 1 d . . . . .
H17A H 0.6071 0.0940 0.3168 0.050 Uiso 1 1 calc R U . . .
H17B H 0.6833 0.2321 0.3561 0.050 Uiso 1 1 calc R U . . .
C13 C 0.4226(2) 0.7337(3) 0.28450(13) 0.0421(5) Uani 1 1 d . . . . .
H13 H 0.4513 0.8076 0.2558 0.050 Uiso 1 1 calc R U . . .
C6 C 0.18908(19) 0.1025(2) 0.57188(10) 0.0295(4) Uani 1 1 d . . . . .
H6A H 0.2387 0.1369 0.6145 0.035 Uiso 1 1 calc R U . . .
H6B H 0.2184 -0.0009 0.5630 0.035 Uiso 1 1 calc R U . . .
C3 C -0.1437(2) 0.0166(3) 0.62346(11) 0.0361(5) Uani 1 1 d . . . . .
H3 H -0.1832 -0.0469 0.6529 0.043 Uiso 1 1 calc R U . . .
C12 C 0.5093(2) 0.6753(3) 0.33626(14) 0.0443(6) Uani 1 1 d . . . . .
H12 H 0.5974 0.7106 0.3434 0.053 Uiso 1 1 calc R U . . .
C14 C 0.2935(2) 0.6838(3) 0.27484(11) 0.0354(5) Uani 1 1 d . . . . .
H14 H 0.2329 0.7247 0.2399 0.042 Uiso 1 1 calc R U . . .
C18 C 0.6050(3) 0.2868(4) 0.26011(13) 0.0527(7) Uani 1 1 d . . . . .
H18A H 0.5281 0.2566 0.2289 0.079 Uiso 1 1 calc R U . . .
H18B H 0.6853 0.2626 0.2410 0.079 Uiso 1 1 calc R U . . .
H18C H 0.6015 0.3954 0.2682 0.079 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9080(15) . ?
Cu1 N2 1.9112(15) . ?
Cu1 N1 1.9764(17) . ?
Cu1 O11 1.9835(13) . ?
Cu1 O11 2.3997(15) 3_566 ?
O3 C16 1.332(2) . ?
O3 C17 1.455(2) . ?
O2 C16 1.215(2) . ?
O11 N11 1.312(2) . ?
O11 Cu1 2.3998(15) 3_566 ?
O12 N11 1.221(2) . ?
O1 C9 1.283(2) . ?
C15 C14 1.383(3) . ?
C15 C10 1.399(3) . ?
C15 H15 0.9500 . ?
N1 C5 1.349(2) . ?
N1 C1 1.349(3) . ?
O13 N11 1.219(2) . ?
N2 C7 1.298(3) . ?
N2 C6 1.459(3) . ?
C10 C11 1.387(3) . ?
C10 C9 1.492(3) . ?
C8 C9 1.406(3) . ?
C8 C7 1.418(3) . ?
C8 C16 1.476(3) . ?
C2 C1 1.372(3) . ?
C2 C3 1.389(3) . ?
C2 H2 0.9500 . ?
C11 C12 1.380(3) . ?
C11 H11 0.9500 . ?
C5 C4 1.380(3) . ?
C5 C6 1.502(3) . ?
C1 H1 0.9500 . ?
C4 C3 1.383(3) . ?
C4 H4 0.9500 . ?
C7 H7 0.9500 . ?
C17 C18 1.497(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C13 C12 1.383(3) . ?
C13 C14 1.386(3) . ?
C13 H13 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C3 H3 0.9500 . ?
C12 H12 0.9500 . ?
C14 H14 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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 N2 92.35(6) . . ?
O1 Cu1 N1 174.90(6) . . ?
N2 Cu1 N1 83.78(7) . . ?
O1 Cu1 O11 89.41(6) . . ?
N2 Cu1 O11 177.12(7) . . ?
N1 Cu1 O11 94.33(6) . . ?
O1 Cu1 O11 88.51(6) . 3_566 ?
N2 Cu1 O11 106.91(6) . 3_566 ?
N1 Cu1 O11 95.78(6) . 3_566 ?
O11 Cu1 O11 75.41(6) . 3_566 ?
C16 O3 C17 116.29(15) . . ?
N11 O11 Cu1 117.20(11) . . ?
N11 O11 Cu1 124.89(12) . 3_566 ?
Cu1 O11 Cu1 104.59(6) . 3_566 ?
C9 O1 Cu1 128.66(13) . . ?
C14 C15 C10 120.70(19) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C5 N1 C1 118.96(18) . . ?
C5 N1 Cu1 114.30(13) . . ?
C1 N1 Cu1 126.72(13) . . ?
C7 N2 C6 119.55(16) . . ?
C7 N2 Cu1 125.01(14) . . ?
C6 N2 Cu1 115.07(12) . . ?
C11 C10 C15 118.8(2) . . ?
C11 C10 C9 122.43(17) . . ?
C15 C10 C9 118.59(17) . . ?
C9 C8 C7 122.58(17) . . ?
C9 C8 C16 123.73(18) . . ?
C7 C8 C16 113.64(16) . . ?
O1 C9 C8 123.18(19) . . ?
O1 C9 C10 112.57(16) . . ?
C8 C9 C10 124.12(17) . . ?
O2 C16 O3 122.84(19) . . ?
O2 C16 C8 123.57(19) . . ?
O3 C16 C8 113.51(15) . . ?
C1 C2 C3 118.9(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
O13 N11 O12 124.16(18) . . ?
O13 N11 O11 116.96(17) . . ?
O12 N11 O11 118.88(16) . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
N1 C5 C4 121.62(18) . . ?
N1 C5 C6 115.87(18) . . ?
C4 C5 C6 122.49(18) . . ?
N1 C1 C2 122.13(19) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C5 C4 C3 119.17(19) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N2 C7 C8 126.13(17) . . ?
N2 C7 H7 116.9 . . ?
C8 C7 H7 116.9 . . ?
O3 C17 C18 107.03(18) . . ?
O3 C17 H17A 110.3 . . ?
C18 C17 H17A 110.3 . . ?
O3 C17 H17B 110.3 . . ?
C18 C17 H17B 110.3 . . ?
H17A C17 H17B 108.6 . . ?
C12 C13 C14 119.5(2) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
N2 C6 C5 109.83(15) . . ?
N2 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C4 C3 C2 119.2(2) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C11 C12 C13 120.8(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C15 C10 C11 1.7(3) . . . . ?
C14 C15 C10 C9 176.94(18) . . . . ?
Cu1 O1 C9 C8 -3.8(3) . . . . ?
Cu1 O1 C9 C10 -179.94(12) . . . . ?
C7 C8 C9 O1 -8.9(3) . . . . ?
C16 C8 C9 O1 168.42(18) . . . . ?
C7 C8 C9 C10 166.79(18) . . . . ?
C16 C8 C9 C10 -15.9(3) . . . . ?
C11 C10 C9 O1 135.4(2) . . . . ?
C15 C10 C9 O1 -39.6(3) . . . . ?
C11 C10 C9 C8 -40.7(3) . . . . ?
C15 C10 C9 C8 144.3(2) . . . . ?
C17 O3 C16 O2 -8.4(3) . . . . ?
C17 O3 C16 C8 174.88(18) . . . . ?
C9 C8 C16 O2 155.5(2) . . . . ?
C7 C8 C16 O2 -27.0(3) . . . . ?
C9 C8 C16 O3 -27.8(3) . . . . ?
C7 C8 C16 O3 149.77(18) . . . . ?
Cu1 O11 N11 O13 -157.96(16) . . . . ?
Cu1 O11 N11 O13 -23.2(2) 3_566 . . . ?
Cu1 O11 N11 O12 22.7(2) . . . . ?
Cu1 O11 N11 O12 157.40(14) 3_566 . . . ?
C15 C10 C11 C12 -1.8(3) . . . . ?
C9 C10 C11 C12 -176.8(2) . . . . ?
C1 N1 C5 C4 0.9(3) . . . . ?
Cu1 N1 C5 C4 179.50(15) . . . . ?
C1 N1 C5 C6 -177.86(17) . . . . ?
Cu1 N1 C5 C6 0.7(2) . . . . ?
C5 N1 C1 C2 -0.2(3) . . . . ?
Cu1 N1 C1 C2 -178.58(15) . . . . ?
C3 C2 C1 N1 0.1(3) . . . . ?
N1 C5 C4 C3 -1.5(3) . . . . ?
C6 C5 C4 C3 177.14(19) . . . . ?
C6 N2 C7 C8 178.59(19) . . . . ?
Cu1 N2 C7 C8 5.9(3) . . . . ?
C9 C8 C7 N2 7.7(3) . . . . ?
C16 C8 C7 N2 -169.85(19) . . . . ?
C16 O3 C17 C18 -162.3(2) . . . . ?
C7 N2 C6 C5 -161.61(17) . . . . ?
Cu1 N2 C6 C5 11.7(2) . . . . ?
N1 C5 C6 N2 -7.9(2) . . . . ?
C4 C5 C6 N2 173.35(18) . . . . ?
C5 C4 C3 C2 1.4(3) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C14 C13 C12 C11 1.1(4) . . . . ?
C10 C15 C14 C13 -0.3(3) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?

_refine_diff_density_max         0.286
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_cl061
_database_code_depnum_ccdc_archive 'CCDC 1566615'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;
_chemical_name_common            '[CuL30aOAc]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H36 Cu2 N4 O10'
_chemical_formula_sum            'C30 H36 Cu2 N4 O10'
_chemical_formula_weight         739.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   7.5927(5)
_cell_length_b                   23.9283(12)
_cell_length_c                   8.5927(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.078(5)
_cell_angle_gamma                90
_cell_volume                     1558.87(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    7388
_cell_measurement_theta_min      1.70
_cell_measurement_theta_max      27.98

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_F_000             764
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.097
_exptl_absorpt_coefficient_mu    1.428
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            9798
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.702
_diffrn_reflns_theta_max         28.079
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             3530
_reflns_number_gt                2653
_reflns_threshold_expression     'I > 2σ(I)'


_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0253P)²] 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         3530
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0652
_refine_ls_wR_factor_gt          0.0618
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_restrained_S_all      0.909
_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
C1 C 0.9238(3) 1.11686(9) 0.1590(2) 0.0219(5) Uani 1 1 d . . . . .
H1 H 1.0112 1.1170 0.0839 0.026 Uiso 1 1 calc R U . . .
C2 C 0.8395(3) 1.16603(9) 0.1907(2) 0.0231(5) Uani 1 1 d . . . . .
H2 H 0.8681 1.1996 0.1388 0.028 Uiso 1 1 calc R U . . .
C3 C 0.7116(3) 1.16549(10) 0.3004(3) 0.0249(5) Uani 1 1 d . . . . .
H3 H 0.6525 1.1990 0.3258 0.030 Uiso 1 1 calc R U . . .
C4 C 0.6712(3) 1.11597(9) 0.3720(2) 0.0208(5) Uani 1 1 d . . . . .
H4 H 0.5822 1.1148 0.4454 0.025 Uiso 1 1 calc R U . . .
C5 C 0.7622(3) 1.06787(9) 0.3354(2) 0.0165(4) Uani 1 1 d . . . . .
C6 C 0.7239(3) 1.01250(9) 0.4077(2) 0.0186(4) Uani 1 1 d . . . . .
H6A H 0.7368 1.0156 0.5227 0.022 Uiso 1 1 calc R U . . .
H6B H 0.6009 1.0013 0.3789 0.022 Uiso 1 1 calc R U . . .
C7 C 0.8381(3) 0.92071(9) 0.4147(2) 0.0177(4) Uani 1 1 d . . . . .
H7 H 0.7544 0.9154 0.4917 0.021 Uiso 1 1 calc R U . . .
C8 C 0.9430(3) 0.87342(9) 0.3778(2) 0.0167(4) Uani 1 1 d . . . . .
C9 C 1.0813(3) 0.87735(9) 0.2734(2) 0.0177(4) Uani 1 1 d . . . . .
C10 C 1.1983(4) 0.82867(10) 0.2380(3) 0.0258(5) Uani 1 1 d . . . . .
H10A H 1.2880 0.8408 0.1673 0.039 Uiso 1 1 calc R U . . .
H10B H 1.1269 0.7988 0.1885 0.039 Uiso 1 1 calc R U . . .
H10C H 1.2562 0.8147 0.3350 0.039 Uiso 1 1 calc R U . . .
C11 C 0.9112(3) 0.82129(9) 0.4610(2) 0.0196(5) Uani 1 1 d . . . . .
C12 C 0.7376(4) 0.78029(10) 0.6540(2) 0.0251(5) Uani 1 1 d . . . . .
H12A H 0.6640 0.7947 0.7368 0.030 Uiso 1 1 calc R U . . .
H12B H 0.8540 0.7700 0.7032 0.030 Uiso 1 1 calc R U . . .
C13 C 0.6518(4) 0.72892(11) 0.5834(3) 0.0347(6) Uani 1 1 d . . . . .
H13A H 0.5416 0.7394 0.5262 0.052 Uiso 1 1 calc R U . . .
H13B H 0.6264 0.7024 0.6663 0.052 Uiso 1 1 calc R U . . .
H13C H 0.7315 0.7114 0.5118 0.052 Uiso 1 1 calc R U . . .
C14 C 1.3003(3) 1.04429(9) 0.1068(2) 0.0181(4) Uani 1 1 d . . . . .
C15 C 1.4236(3) 1.07137(11) -0.0030(3) 0.0265(5) Uani 1 1 d . . . . .
H15A H 1.4108 1.1121 0.0019 0.040 Uiso 1 1 calc R U . . .
H15B H 1.3945 1.0585 -0.1096 0.040 Uiso 1 1 calc R U . . .
H15C H 1.5455 1.0610 0.0275 0.040 Uiso 1 1 calc R U . . .
N1 N 0.8866(2) 1.06836(7) 0.23077(18) 0.0161(4) Uani 1 1 d . . . . .
N2 N 0.8459(2) 0.96990(7) 0.35387(18) 0.0162(4) Uani 1 1 d . . . . .
O1 O 1.1168(2) 0.92189(7) 0.20178(16) 0.0213(3) Uani 1 1 d . . . . .
O2 O 1.0016(2) 0.77940(7) 0.46385(16) 0.0249(4) Uani 1 1 d . . . . .
O3 O 0.7615(2) 0.82397(7) 0.54143(17) 0.0240(4) Uani 1 1 d . . . . .
O4 O 1.1590(2) 1.02249(6) 0.04323(15) 0.0181(3) Uani 1 1 d . . . . .
O5 O 1.3346(2) 1.04428(7) 0.24827(16) 0.0262(4) Uani 1 1 d . . . . .
Cu1 Cu 0.99921(4) 0.99395(2) 0.19553(3) 0.01599(8) 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
C1 N1 1.351(3) . ?
C1 C2 1.373(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.338(3) . ?
C5 C6 1.499(3) . ?
C6 N2 1.469(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.290(3) . ?
C7 C8 1.429(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.420(3) . ?
C8 C11 1.464(3) . ?
C9 O1 1.267(3) . ?
C9 C10 1.506(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O2 1.215(3) . ?
C11 O3 1.363(3) . ?
C12 O3 1.442(3) . ?
C12 C13 1.504(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 O5 1.230(2) . ?
C14 O4 1.288(3) . ?
C14 C15 1.510(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N1 Cu1 2.0050(18) . ?
N2 Cu1 1.9256(18) . ?
O1 Cu1 1.9414(16) . ?
O4 Cu1 1.9547(15) . ?
O4 Cu1 2.3541(13) 3_775 ?
Cu1 O4 2.3541(13) 3_775 ?

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
N1 C1 C2 122.3(2) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 118.4(2) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 119.4(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 119.2(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 121.5(2) . . ?
N1 C5 C6 116.50(19) . . ?
C4 C5 C6 122.0(2) . . ?
N2 C6 C5 110.06(18) . . ?
N2 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
N2 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 126.4(2) . . ?
N2 C7 H7 116.8 . . ?
C8 C7 H7 116.8 . . ?
C9 C8 C7 121.8(2) . . ?
C9 C8 C11 120.8(2) . . ?
C7 C8 C11 117.2(2) . . ?
O1 C9 C8 123.1(2) . . ?
O1 C9 C10 114.1(2) . . ?
C8 C9 C10 122.7(2) . . ?
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 . . ?
O2 C11 O3 120.9(2) . . ?
O2 C11 C8 127.2(2) . . ?
O3 C11 C8 111.8(2) . . ?
O3 C12 C13 112.91(18) . . ?
O3 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
O3 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 O4 123.1(2) . . ?
O5 C14 C15 120.8(2) . . ?
O4 C14 C15 116.06(17) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 N1 C1 119.1(2) . . ?
C5 N1 Cu1 114.55(14) . . ?
C1 N1 Cu1 126.35(16) . . ?
C7 N2 C6 117.52(19) . . ?
C7 N2 Cu1 126.97(16) . . ?
C6 N2 Cu1 115.50(13) . . ?
C9 O1 Cu1 130.62(15) . . ?
C11 O3 C12 116.39(18) . . ?
C14 O4 Cu1 112.99(12) . . ?
C14 O4 Cu1 144.26(13) . 3_775 ?
Cu1 O4 Cu1 102.65(6) . 3_775 ?
N2 Cu1 O1 90.55(7) . . ?
N2 Cu1 O4 176.33(7) . . ?
O1 Cu1 O4 91.59(7) . . ?
N2 Cu1 N1 83.10(7) . . ?
O1 Cu1 N1 169.67(6) . . ?
O4 Cu1 N1 94.35(7) . . ?
N2 Cu1 O4 105.44(6) . 3_775 ?
O1 Cu1 O4 95.05(6) . 3_775 ?
O4 Cu1 O4 77.35(6) . 3_775 ?
N1 Cu1 O4 94.49(6) . 3_775 ?

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
N1 C1 C2 C3 -0.1(3) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C3 C4 C5 N1 -0.9(3) . . . . ?
C3 C4 C5 C6 -179.43(19) . . . . ?
N1 C5 C6 N2 4.3(2) . . . . ?
C4 C5 C6 N2 -177.06(17) . . . . ?
N2 C7 C8 C9 4.8(3) . . . . ?
N2 C7 C8 C11 -179.65(19) . . . . ?
C7 C8 C9 O1 -2.8(3) . . . . ?
C11 C8 C9 O1 -178.19(18) . . . . ?
C7 C8 C9 C10 177.39(19) . . . . ?
C11 C8 C9 C10 2.0(3) . . . . ?
C9 C8 C11 O2 7.3(3) . . . . ?
C7 C8 C11 O2 -168.3(2) . . . . ?
C9 C8 C11 O3 -173.13(17) . . . . ?
C7 C8 C11 O3 11.3(3) . . . . ?
C4 C5 N1 C1 -0.2(3) . . . . ?
C6 C5 N1 C1 178.42(18) . . . . ?
C4 C5 N1 Cu1 -179.57(15) . . . . ?
C6 C5 N1 Cu1 -0.9(2) . . . . ?
C2 C1 N1 C5 0.7(3) . . . . ?
C2 C1 N1 Cu1 180.00(15) . . . . ?
C8 C7 N2 C6 179.30(18) . . . . ?
C8 C7 N2 Cu1 0.4(3) . . . . ?
C5 C6 N2 C7 175.07(17) . . . . ?
C5 C6 N2 Cu1 -5.9(2) . . . . ?
C8 C9 O1 Cu1 -4.2(3) . . . . ?
C10 C9 O1 Cu1 175.61(14) . . . . ?
O2 C11 O3 C12 12.8(3) . . . . ?
C8 C11 O3 C12 -166.79(17) . . . . ?
C13 C12 O3 C11 -85.8(3) . . . . ?
O5 C14 O4 Cu1 3.7(3) . . . . ?
C15 C14 O4 Cu1 -175.33(16) . . . . ?
O5 C14 O4 Cu1 179.20(16) . . . 3_775 ?
C15 C14 O4 Cu1 0.2(4) . . . 3_775 ?

_refine_diff_density_max         0.390
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_cl096
_database_code_depnum_ccdc_archive 'CCDC 1566636'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;
_chemical_name_common            '[CuL30bSCN]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 Cu N3 O3 S'
_chemical_formula_sum            'C14 H17 Cu N3 O3 S'
_chemical_formula_weight         370.90

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'
S S 0.1246 0.1234 '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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   9.8474(5)
_cell_length_b                   15.5449(6)
_cell_length_c                   10.2348(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.590(4)
_cell_angle_gamma                90
_cell_volume                     1565.11(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    11360
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      28.46

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_F_000             764
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.067
_exptl_absorpt_coefficient_mu    1.544
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;??
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            9229
_diffrn_reflns_av_unetI/netI     0.0817
_diffrn_reflns_av_R_equivalents  0.1146
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.384
_diffrn_reflns_theta_max         28.419
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3689
_reflns_number_gt                3020
_reflns_threshold_expression     'I > 2σ(I)'


_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1356P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3689
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0659
_refine_ls_wR_factor_ref         0.2042
_refine_ls_wR_factor_gt          0.1957
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
C1 C -0.0678(4) 0.2391(2) 0.8694(4) 0.0328(8) Uani 1 1 d . . . . .
H1 H -0.1551 0.2283 0.8293 0.039 Uiso 1 1 calc R U . . .
C2 C -0.0338(5) 0.3220(3) 0.9052(4) 0.0400(10) Uani 1 1 d . . . . .
H2 H -0.0958 0.3681 0.8890 0.048 Uiso 1 1 calc R U . . .
C3 C 0.0942(5) 0.3368(2) 0.9658(4) 0.0372(9) Uani 1 1 d . . . . .
H3 H 0.1206 0.3935 0.9909 0.045 Uiso 1 1 calc R U . . .
C4 C 0.1822(5) 0.2688(2) 0.9891(4) 0.0343(8) Uani 1 1 d . . . . .
H4 H 0.2688 0.2777 1.0314 0.041 Uiso 1 1 calc R U . . .
C5 C 0.1409(4) 0.1866(2) 0.9489(3) 0.0282(7) Uani 1 1 d . . . . .
C6 C 0.2317(4) 0.1092(2) 0.9665(4) 0.0314(8) Uani 1 1 d . . . . .
H6A H 0.3188 0.1198 0.9247 0.038 Uiso 1 1 calc R U . . .
H6B H 0.2515 0.0988 1.0608 0.038 Uiso 1 1 calc R U . . .
C7 C 0.2358(4) -0.0376(2) 0.9083(3) 0.0238(7) Uani 1 1 d . . . . .
H7 H 0.3246 -0.0354 0.9486 0.029 Uiso 1 1 calc R U . . .
C8 C 0.1921(4) -0.1187(2) 0.8544(3) 0.0236(7) Uani 1 1 d . . . . .
C9 C 0.0612(4) -0.1286(2) 0.7926(3) 0.0261(7) Uani 1 1 d . . . . .
C10 C 0.0126(4) -0.2117(2) 0.7320(4) 0.0341(8) Uani 1 1 d . . . . .
H10A H -0.0831 -0.2061 0.7025 0.051 Uiso 1 1 calc R U . . .
H10B H 0.0219 -0.2580 0.7968 0.051 Uiso 1 1 calc R U . . .
H10C H 0.0672 -0.2254 0.6570 0.051 Uiso 1 1 calc R U . . .
C11 C 0.2877(4) -0.1902(2) 0.8683(3) 0.0260(7) Uani 1 1 d . . . . .
C12 C 0.4272(4) -0.1746(3) 0.9302(4) 0.0334(8) Uani 1 1 d . . . . .
H12A H 0.4195 -0.1607 1.0229 0.050 Uiso 1 1 calc R U . . .
H12B H 0.4702 -0.1265 0.8860 0.050 Uiso 1 1 calc R U . . .
H12C H 0.4827 -0.2265 0.9218 0.050 Uiso 1 1 calc R U . . .
C13 C -0.3187(4) 0.0543(2) 0.7642(4) 0.0272(7) Uani 1 1 d . . . . .
C22 C 0.1623(5) 0.0363(3) 0.5538(4) 0.0360(9) Uani 1 1 d . . . . .
H22A H 0.2520 0.0319 0.5988 0.054 Uiso 1 1 calc R U . . .
H22B H 0.1725 0.0579 0.4648 0.054 Uiso 1 1 calc R U . . .
H22C H 0.1194 -0.0205 0.5499 0.054 Uiso 1 1 calc R U . . .
N1 N 0.0190(3) 0.17269(19) 0.8895(3) 0.0274(6) Uani 1 1 d . . . . .
N2 N 0.1650(3) 0.0335(2) 0.9073(3) 0.0275(6) Uani 1 1 d . . . . .
N13 N -0.2022(4) 0.0684(2) 0.7746(4) 0.0345(7) Uani 1 1 d . . . . .
O1 O -0.0257(3) -0.06839(17) 0.7809(3) 0.0291(5) Uani 1 1 d . . . . .
O2 O 0.2589(3) -0.26435(17) 0.8313(3) 0.0363(6) Uani 1 1 d . . . . .
O21 O 0.0795(3) 0.09417(17) 0.6234(3) 0.0316(6) Uani 1 1 d . . . . .
H21 H 0.1233 0.1395 0.6406 0.038 Uiso 1 1 calc R U . . .
S13 S -0.48165(11) 0.03681(7) 0.74946(10) 0.0342(3) Uani 1 1 d . . . . .
Cu1 Cu -0.01068(5) 0.05270(3) 0.82340(4) 0.0262(2) 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
C1 N1 1.350(5) . ?
C1 C2 1.378(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.399(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(5) . ?
C4 H4 0.9500 . ?
C5 N1 1.339(5) . ?
C5 C6 1.505(5) . ?
C6 N2 1.465(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.307(5) . ?
C7 C8 1.434(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.419(5) . ?
C8 C11 1.459(5) . ?
C9 O1 1.270(4) . ?
C9 C10 1.502(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O2 1.242(4) . ?
C11 C12 1.507(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N13 1.168(6) . ?
C13 S13 1.628(4) . ?
C22 O21 1.426(5) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
N1 Cu1 2.001(3) . ?
N2 Cu1 1.920(3) . ?
N13 Cu1 1.944(4) . ?
O1 Cu1 1.936(3) . ?
O21 Cu1 2.358(3) . ?
O21 H21 0.8400 . ?

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
N1 C1 C2 122.0(4) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C1 C2 C3 118.4(4) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 119.7(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 118.6(4) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 121.6(4) . . ?
N1 C5 C6 116.2(3) . . ?
C4 C5 C6 122.2(4) . . ?
N2 C6 C5 109.9(3) . . ?
N2 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 126.1(3) . . ?
N2 C7 H7 116.9 . . ?
C8 C7 H7 116.9 . . ?
C9 C8 C7 121.2(3) . . ?
C9 C8 C11 122.0(3) . . ?
C7 C8 C11 116.8(3) . . ?
O1 C9 C8 123.8(3) . . ?
O1 C9 C10 113.2(3) . . ?
C8 C9 C10 122.9(3) . . ?
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 . . ?
O2 C11 C8 122.7(3) . . ?
O2 C11 C12 117.9(3) . . ?
C8 C11 C12 119.4(3) . . ?
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 . . ?
N13 C13 S13 178.8(3) . . ?
O21 C22 H22A 109.5 . . ?
O21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C5 N1 C1 119.7(3) . . ?
C5 N1 Cu1 114.7(2) . . ?
C1 N1 Cu1 125.4(3) . . ?
C7 N2 C6 116.6(3) . . ?
C7 N2 Cu1 127.2(3) . . ?
C6 N2 Cu1 116.0(3) . . ?
C13 N13 Cu1 159.5(3) . . ?
C9 O1 Cu1 130.6(2) . . ?
C22 O21 Cu1 120.5(2) . . ?
C22 O21 H21 109.5 . . ?
Cu1 O21 H21 104.9 . . ?
N2 Cu1 O1 90.45(13) . . ?
N2 Cu1 N13 168.09(14) . . ?
O1 Cu1 N13 90.06(13) . . ?
N2 Cu1 N1 83.04(14) . . ?
O1 Cu1 N1 172.19(12) . . ?
N13 Cu1 N1 95.43(14) . . ?
N2 Cu1 O21 93.65(12) . . ?
O1 Cu1 O21 95.66(10) . . ?
N13 Cu1 O21 98.14(13) . . ?
N1 Cu1 O21 89.07(11) . . ?

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
N1 C1 C2 C3 -0.9(6) . . . . ?
C1 C2 C3 C4 -0.5(6) . . . . ?
C2 C3 C4 C5 1.0(6) . . . . ?
C3 C4 C5 N1 -0.3(5) . . . . ?
C3 C4 C5 C6 178.1(3) . . . . ?
N1 C5 C6 N2 2.3(5) . . . . ?
C4 C5 C6 N2 -176.1(3) . . . . ?
N2 C7 C8 C9 -0.2(5) . . . . ?
N2 C7 C8 C11 -179.2(3) . . . . ?
C7 C8 C9 O1 -0.4(5) . . . . ?
C11 C8 C9 O1 178.6(3) . . . . ?
C7 C8 C9 C10 178.5(3) . . . . ?
C11 C8 C9 C10 -2.5(5) . . . . ?
C9 C8 C11 O2 -2.7(5) . . . . ?
C7 C8 C11 O2 176.4(3) . . . . ?
C9 C8 C11 C12 177.6(3) . . . . ?
C7 C8 C11 C12 -3.4(5) . . . . ?
C4 C5 N1 C1 -1.1(5) . . . . ?
C6 C5 N1 C1 -179.5(3) . . . . ?
C4 C5 N1 Cu1 173.7(3) . . . . ?
C6 C5 N1 Cu1 -4.7(4) . . . . ?
C2 C1 N1 C5 1.7(5) . . . . ?
C2 C1 N1 Cu1 -172.5(3) . . . . ?
C8 C7 N2 C6 -178.9(3) . . . . ?
C8 C7 N2 Cu1 -4.9(5) . . . . ?
C5 C6 N2 C7 176.0(3) . . . . ?
C5 C6 N2 Cu1 1.3(4) . . . . ?
C8 C9 O1 Cu1 6.2(5) . . . . ?
C10 C9 O1 Cu1 -172.8(2) . . . . ?

_refine_diff_density_max         1.351
_refine_diff_density_min         -1.284
_refine_diff_density_rms         0.146

####################################################################### 
# 
# 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_cl125
_database_code_depnum_ccdc_archive 'CCDC 1566617'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;


# start Validation Reply Form
_vrf_PLAT306_cl125               
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......        O21 Check 
RESPONSE: Refinement not stable upon adding H-atoms
;
_vrf_PLAT430_cl125               
;
PROBLEM: Short Inter D...A Contact  O3     ..  O27     ..       2.76 Ang.  
RESPONSE: Refinement not stable upon adding H-atoms
;
_vrf_PLAT975_cl125               
;
PROBLEM: Check Calcd Residual Density  1.05A From     O25       1.62 eA-3  
RESPONSE: Refinement not stable upon adding H-atoms
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;
_chemical_name_common            '[CuL30dOAc]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 Cu N3 O4, 7(H2O)'
_chemical_formula_sum            'C14 H29 Cu N3 O11'
_chemical_formula_weight         478.94

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 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                   6.8193(4)
_cell_length_b                   11.6812(6)
_cell_length_c                   28.7206(16)
_cell_angle_alpha                90
_cell_angle_beta                 95.047(4)
_cell_angle_gamma                90
_cell_volume                     2278.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    16445
_cell_measurement_theta_min      1.49
_cell_measurement_theta_max      26.02

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             948
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.132
_exptl_absorpt_coefficient_mu    1.012
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            25851
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_av_R_equivalents  0.0791
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         1.424
_diffrn_reflns_theta_max         28.515
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             5514
_reflns_number_gt                3886
_reflns_threshold_expression     'I > 2σ(I)'


_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1072P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5514
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1665
_refine_ls_wR_factor_gt          0.1517
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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
C1 C 0.7826(5) 0.4594(3) 0.23176(12) 0.0243(7) Uani 1 1 d . . . . .
H1 H 0.7472 0.4900 0.2605 0.029 Uiso 1 1 calc R U . . .
C2 C 0.8186(5) 0.5341(3) 0.19605(13) 0.0269(7) Uani 1 1 d . . . . .
H2 H 0.8086 0.6145 0.2001 0.032 Uiso 1 1 calc R U . . .
C3 C 0.8696(5) 0.4887(3) 0.15426(13) 0.0282(7) Uani 1 1 d . . . . .
H3 H 0.8948 0.5379 0.1291 0.034 Uiso 1 1 calc R U . . .
C4 C 0.8835(5) 0.3708(3) 0.14931(12) 0.0278(7) Uani 1 1 d . . . . .
H4 H 0.9193 0.3382 0.1210 0.033 Uiso 1 1 calc R U . . .
C5 C 0.8443(5) 0.3019(3) 0.18642(12) 0.0239(6) Uani 1 1 d . . . . .
C6 C 0.8565(6) 0.1733(3) 0.18391(13) 0.0324(8) Uani 1 1 d . . . . .
H6A H 0.7737 0.1453 0.1562 0.039 Uiso 1 1 calc R U . . .
H6B H 0.9941 0.1498 0.1808 0.039 Uiso 1 1 calc R U . . .
C7 C 0.7585(5) 0.0133(3) 0.22741(12) 0.0235(6) Uani 1 1 d . . . . .
H7 H 0.7770 -0.0292 0.1999 0.028 Uiso 1 1 calc R U . . .
C8 C 0.7007(5) -0.0474(3) 0.26617(12) 0.0243(7) Uani 1 1 d . . . . .
C9 C 0.6756(5) 0.0045(3) 0.31000(12) 0.0231(6) Uani 1 1 d . . . . .
C10 C 0.6251(6) -0.0196(3) 0.39006(12) 0.0306(7) Uani 1 1 d . . . . .
H10A H 0.5113 0.0331 0.3900 0.037 Uiso 1 1 calc R U . . .
H10B H 0.7466 0.0237 0.3998 0.037 Uiso 1 1 calc R U . . .
C11 C 0.6011(7) -0.1182(4) 0.42278(15) 0.0447(10) Uani 1 1 d . . . . .
H11A H 0.4697 -0.1516 0.4163 0.067 Uiso 1 1 calc R U . . .
H11B H 0.6168 -0.0908 0.4551 0.067 Uiso 1 1 calc R U . . .
H11C H 0.7011 -0.1764 0.4183 0.067 Uiso 1 1 calc R U . . .
C12 C 0.6699(5) -0.1670(3) 0.26157(13) 0.0275(7) Uani 1 1 d . . . . .
C13 C 0.8726(5) 0.3439(3) 0.34988(12) 0.0285(7) Uani 1 1 d . . . . .
C14 C 0.8785(7) 0.4046(5) 0.39617(17) 0.0556(14) Uani 1 1 d . . . . .
H14A H 0.8715 0.3482 0.4212 0.083 Uiso 1 1 calc R U . . .
H14B H 0.7664 0.4571 0.3961 0.083 Uiso 1 1 calc R U . . .
H14C H 1.0015 0.4480 0.4013 0.083 Uiso 1 1 calc R U . . .
Cu1 Cu 0.73852(6) 0.22988(3) 0.27465(2) 0.02095(14) Uani 1 1 d . . . . .
N1 N 0.7960(4) 0.3459(2) 0.22720(9) 0.0222(5) Uani 1 1 d . . . . .
N2 N 0.7887(4) 0.1234(2) 0.22620(9) 0.0243(6) Uani 1 1 d . . . . .
N3 N 0.6405(5) -0.2637(3) 0.25752(13) 0.0373(8) Uani 1 1 d . . . . .
O1 O 0.6898(3) 0.10872(19) 0.31890(8) 0.0242(5) Uani 1 1 d . . . . .
O2 O 0.6365(3) -0.0685(2) 0.34373(8) 0.0267(5) Uani 1 1 d . . . . .
O3 O 0.7050(3) 0.3374(2) 0.32583(8) 0.0257(5) Uani 1 1 d . . . . .
O4 O 1.0255(4) 0.3029(2) 0.33590(9) 0.0314(5) Uani 1 1 d . . . . .
O21 O 0.0398(5) 0.6820(3) 0.44369(13) 0.0518(8) Uani 1 1 d . . . . .
O22 O 0.8645(4) 0.5619(3) 0.04413(10) 0.0402(7) Uani 1 1 d . . . . .
O23 O 0.6965(5) 0.6109(3) 0.48372(11) 0.0442(7) Uani 1 1 d . . . . .
O24 O 0.4400(4) 0.2147(2) 0.46072(10) 0.0382(6) Uani 1 1 d . . . . .
O25 O 0.3529(5) 0.5319(3) 0.43516(14) 0.0610(10) Uani 1 1 d . . . . .
O26 O 0.8127(4) 0.1475(3) 0.49814(11) 0.0426(7) Uani 1 1 d . . . . .
O27 O 0.3866(4) 0.3407(2) 0.37907(8) 0.0287(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
C1 N1 1.337(4) . ?
C1 C2 1.384(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.384(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(5) . ?
C4 H4 0.9500 . ?
C5 N1 1.346(4) . ?
C5 C6 1.507(5) . ?
C6 N2 1.459(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.303(5) . ?
C7 C8 1.405(5) . ?
C7 H7 0.9500 . ?
C8 C12 1.417(5) . ?
C8 C9 1.421(5) . ?
C9 O1 1.246(4) . ?
C9 O2 1.335(4) . ?
C10 O2 1.457(4) . ?
C10 C11 1.504(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N3 1.152(5) . ?
C13 O4 1.245(4) . ?
C13 O3 1.284(4) . ?
C13 C14 1.504(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
Cu1 N2 1.920(3) . ?
Cu1 O1 1.950(2) . ?
Cu1 O3 1.962(2) . ?
Cu1 N1 1.985(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.3(3) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C3 C2 C1 118.4(3) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 118.7(3) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
N1 C5 C4 121.9(3) . . ?
N1 C5 C6 116.2(3) . . ?
C4 C5 C6 122.0(3) . . ?
N2 C6 C5 109.6(3) . . ?
N2 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 125.1(3) . . ?
N2 C7 H7 117.4 . . ?
C8 C7 H7 117.4 . . ?
C7 C8 C12 118.2(3) . . ?
C7 C8 C9 123.4(3) . . ?
C12 C8 C9 118.3(3) . . ?
O1 C9 O2 119.5(3) . . ?
O1 C9 C8 125.8(3) . . ?
O2 C9 C8 114.7(3) . . ?
O2 C10 C11 106.7(3) . . ?
O2 C10 H10A 110.4 . . ?
C11 C10 H10A 110.4 . . ?
O2 C10 H10B 110.4 . . ?
C11 C10 H10B 110.4 . . ?
H10A C10 H10B 108.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C8 178.5(4) . . ?
O4 C13 O3 122.3(3) . . ?
O4 C13 C14 120.5(3) . . ?
O3 C13 C14 117.2(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 Cu1 O1 93.07(11) . . ?
N2 Cu1 O3 176.29(11) . . ?
O1 Cu1 O3 86.49(10) . . ?
N2 Cu1 N1 83.47(12) . . ?
O1 Cu1 N1 176.39(10) . . ?
O3 Cu1 N1 96.90(11) . . ?
C1 N1 C5 119.2(3) . . ?
C1 N1 Cu1 126.2(2) . . ?
C5 N1 Cu1 114.5(2) . . ?
C7 N2 C6 118.6(3) . . ?
C7 N2 Cu1 125.5(2) . . ?
C6 N2 Cu1 115.7(2) . . ?
C9 O1 Cu1 126.2(2) . . ?
C9 O2 C10 116.3(3) . . ?
C13 O3 Cu1 106.5(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.2(5) . . . . ?
C1 C2 C3 C4 -0.1(5) . . . . ?
C2 C3 C4 C5 0.5(5) . . . . ?
C3 C4 C5 N1 -1.0(5) . . . . ?
C3 C4 C5 C6 -179.9(3) . . . . ?
N1 C5 C6 N2 6.7(4) . . . . ?
C4 C5 C6 N2 -174.4(3) . . . . ?
N2 C7 C8 C12 178.7(3) . . . . ?
N2 C7 C8 C9 -2.7(5) . . . . ?
C7 C8 C9 O1 4.4(5) . . . . ?
C12 C8 C9 O1 -177.0(3) . . . . ?
C7 C8 C9 O2 -174.6(3) . . . . ?
C12 C8 C9 O2 4.1(4) . . . . ?
C2 C1 N1 C5 -0.7(5) . . . . ?
C2 C1 N1 Cu1 -177.5(2) . . . . ?
C4 C5 N1 C1 1.1(5) . . . . ?
C6 C5 N1 C1 -180.0(3) . . . . ?
C4 C5 N1 Cu1 178.3(3) . . . . ?
C6 C5 N1 Cu1 -2.8(4) . . . . ?
C8 C7 N2 C6 177.4(3) . . . . ?
C8 C7 N2 Cu1 -6.0(5) . . . . ?
C5 C6 N2 C7 169.2(3) . . . . ?
C5 C6 N2 Cu1 -7.7(4) . . . . ?
O2 C9 O1 Cu1 -178.2(2) . . . . ?
C8 C9 O1 Cu1 2.9(5) . . . . ?
O1 C9 O2 C10 -3.6(4) . . . . ?
C8 C9 O2 C10 175.4(3) . . . . ?
C11 C10 O2 C9 -174.3(3) . . . . ?
O4 C13 O3 Cu1 11.1(4) . . . . ?
C14 C13 O3 Cu1 -169.4(3) . . . . ?

_refine_diff_density_max         1.609
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.138

####################################################################### 
# 
# 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_cl123
_database_code_depnum_ccdc_archive 'CCDC 1566616'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;


# start Validation Reply Form
_vrf_PLAT934_cl123               
;
PROBLEM: Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          6 Check 
RESPONSE: Crystal of low quality
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;
_chemical_name_common            '[CuL30cOAc]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H40 Cu2 N4 O12, 2(H2 O)'
_chemical_formula_sum            'C32 H44 Cu2 N4 O14'
_chemical_formula_weight         835.78

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

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

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

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

_cell_length_a                   8.8660(6)
_cell_length_b                   8.8511(6)
_cell_length_c                   12.7620(8)
_cell_angle_alpha                94.241(5)
_cell_angle_beta                 104.942(5)
_cell_angle_gamma                108.277(5)
_cell_volume                     905.63(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    9512
_cell_measurement_theta_min      1.68
_cell_measurement_theta_max      26.61

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_F_000             434
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.169
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.247
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            10553
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.676
_diffrn_reflns_theta_max         28.601
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             4267
_reflns_number_gt                3604
_reflns_threshold_expression     'I > 2σ(I)'


_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0612P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4267
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.1040
_refine_ls_wR_factor_gt          0.0867
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.140
_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
C1 C 0.5640(3) 0.2467(3) 0.32765(18) 0.0188(4) Uani 1 1 d . . . . .
H1 H 0.6403 0.3544 0.3461 0.023 Uiso 1 1 calc R U . . .
C2 C 0.5538(3) 0.1500(3) 0.23402(19) 0.0215(5) Uani 1 1 d . . . . .
H2 H 0.6216 0.1902 0.1885 0.026 Uiso 1 1 calc R U . . .
C3 C 0.4421(3) -0.0072(3) 0.20825(19) 0.0213(5) Uani 1 1 d . . . . .
H3 H 0.4332 -0.0764 0.1447 0.026 Uiso 1 1 calc R U . . .
C4 C 0.3436(3) -0.0630(3) 0.27527(18) 0.0188(4) Uani 1 1 d . . . . .
H4 H 0.2664 -0.1702 0.2583 0.023 Uiso 1 1 calc R U . . .
C5 C 0.3601(3) 0.0412(3) 0.36804(17) 0.0150(4) Uani 1 1 d . . . . .
C6 C 0.2551(3) -0.0096(3) 0.44354(18) 0.0176(4) Uani 1 1 d . . . . .
H6A H 0.1371 -0.0292 0.4041 0.021 Uiso 1 1 calc R U . . .
H6B H 0.2639 -0.1112 0.4675 0.021 Uiso 1 1 calc R U . . .
C7 C 0.2411(3) 0.0879(3) 0.61675(17) 0.0145(4) Uani 1 1 d . . . . .
H7 H 0.1552 -0.0139 0.6042 0.017 Uiso 1 1 calc R U . . .
C8 C 0.2770(3) 0.1897(3) 0.71691(17) 0.0164(4) Uani 1 1 d . . . . .
C9 C 0.4175(3) 0.3360(3) 0.74861(17) 0.0160(4) Uani 1 1 d . . . . .
C10 C 0.6209(3) 0.5407(3) 0.89372(18) 0.0208(5) Uani 1 1 d . . . . .
H10A H 0.6225 0.6057 0.9609 0.025 Uiso 1 1 calc R U . . .
H10B H 0.6321 0.6113 0.8374 0.025 Uiso 1 1 calc R U . . .
C11 C 0.7641(4) 0.4795(3) 0.9196(2) 0.0338(6) Uani 1 1 d . . . . .
H11A H 0.7434 0.3957 0.9654 0.051 Uiso 1 1 calc R U . . .
H11B H 0.8667 0.5688 0.9592 0.051 Uiso 1 1 calc R U . . .
H11C H 0.7758 0.4340 0.8510 0.051 Uiso 1 1 calc R U . . .
C12 C 0.1775(3) 0.1349(3) 0.79120(18) 0.0173(4) Uani 1 1 d . . . . .
C13 C 0.0003(4) -0.0961(3) 0.8388(2) 0.0264(5) Uani 1 1 d . . . . .
H13A H -0.0852 -0.2012 0.8002 0.032 Uiso 1 1 calc R U . . .
H13B H -0.0572 -0.0232 0.8576 0.032 Uiso 1 1 calc R U . . .
C14 C 0.1111(4) -0.1195(4) 0.9420(2) 0.0355(7) Uani 1 1 d . . . . .
H14A H 0.1699 -0.1896 0.9232 0.053 Uiso 1 1 calc R U . . .
H14B H 0.0437 -0.1696 0.9885 0.053 Uiso 1 1 calc R U . . .
H14C H 0.1921 -0.0146 0.9820 0.053 Uiso 1 1 calc R U . . .
C21 C 0.8075(3) 0.5119(3) 0.57705(17) 0.0159(4) Uani 1 1 d . . . . .
C22 C 0.9444(3) 0.6577(3) 0.5679(2) 0.0223(5) Uani 1 1 d . . . . .
H22A H 1.0492 0.6668 0.6219 0.034 Uiso 1 1 calc R U . . .
H22B H 0.9172 0.7549 0.5821 0.034 Uiso 1 1 calc R U . . .
H22C H 0.9558 0.6464 0.4936 0.034 Uiso 1 1 calc R U . . .
N1 N 0.4687(2) 0.1925(2) 0.39374(15) 0.0154(4) Uani 1 1 d . . . . .
N2 N 0.3122(2) 0.1174(2) 0.53937(14) 0.0147(4) Uani 1 1 d . . . . .
O1 O 0.5028(2) 0.39710(19) 0.68798(12) 0.0176(3) Uani 1 1 d . . . . .
O2 O 0.4631(2) 0.4061(2) 0.85303(13) 0.0212(4) Uani 1 1 d . . . . .
O3 O 0.1631(2) 0.2185(2) 0.86502(14) 0.0221(4) Uani 1 1 d . . . . .
O4 O 0.0968(2) -0.0276(2) 0.76716(14) 0.0236(4) Uani 1 1 d . . . . .
O21 O 0.6579(2) 0.50775(18) 0.53106(12) 0.0158(3) Uani 1 1 d . . . . .
O22 O 0.8364(2) 0.4017(2) 0.62347(15) 0.0243(4) Uani 1 1 d . . . . .
O31 O 1.1560(3) 0.5247(3) 0.7843(2) 0.0362(5) Uani 1 1 d . . . . .
Cu1 Cu 0.47975(3) 0.31535(3) 0.53591(2) 0.01314(10) Uani 1 1 d . . . . .
H31A H 1.067(6) 0.485(6) 0.749(4) 0.054(13) Uiso 1 1 d . . . . .
H31B H 1.170(6) 0.459(6) 0.816(4) 0.058(14) Uiso 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
C1 N1 1.352(3) . ?
C1 C2 1.383(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.388(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.338(3) . ?
C5 C6 1.504(3) . ?
C6 N2 1.462(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.303(3) . ?
C7 C8 1.410(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.430(3) . ?
C8 C12 1.464(3) . ?
C9 O1 1.253(3) . ?
C9 O2 1.329(3) . ?
C10 O2 1.461(3) . ?
C10 C11 1.503(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O3 1.213(3) . ?
C12 O4 1.360(3) . ?
C13 O4 1.447(3) . ?
C13 C14 1.498(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C21 O22 1.238(3) . ?
C21 O21 1.292(3) . ?
C21 C22 1.505(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
N1 Cu1 2.0085(18) . ?
N2 Cu1 1.9211(19) . ?
O1 Cu1 1.9563(15) . ?
O21 Cu1 1.9438(16) . ?
O21 Cu1 2.3518(16) 2_666 ?
O31 H31A 0.75(5) . ?
O31 H31B 0.75(5) . ?
Cu1 O21 2.3518(16) 2_666 ?

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
N1 C1 C2 122.0(2) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C1 C2 C3 118.4(2) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 118.7(2) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 121.7(2) . . ?
N1 C5 C6 116.58(18) . . ?
C4 C5 C6 121.7(2) . . ?
N2 C6 C5 109.39(18) . . ?
N2 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
N2 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 127.4(2) . . ?
N2 C7 H7 116.3 . . ?
C8 C7 H7 116.3 . . ?
C7 C8 C9 119.9(2) . . ?
C7 C8 C12 118.6(2) . . ?
C9 C8 C12 121.23(19) . . ?
O1 C9 O2 118.8(2) . . ?
O1 C9 C8 125.45(19) . . ?
O2 C9 C8 115.7(2) . . ?
O2 C10 C11 110.5(2) . . ?
O2 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
O2 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 O4 121.9(2) . . ?
O3 C12 C8 126.6(2) . . ?
O4 C12 C8 111.41(19) . . ?
O4 C13 C14 110.3(2) . . ?
O4 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
O4 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O22 C21 O21 122.3(2) . . ?
O22 C21 C22 122.2(2) . . ?
O21 C21 C22 115.5(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C5 N1 C1 119.44(19) . . ?
C5 N1 Cu1 114.42(15) . . ?
C1 N1 Cu1 126.07(16) . . ?
C7 N2 C6 117.18(19) . . ?
C7 N2 Cu1 126.38(15) . . ?
C6 N2 Cu1 116.39(14) . . ?
C9 O1 Cu1 128.80(14) . . ?
C9 O2 C10 117.53(18) . . ?
C12 O4 C13 116.13(18) . . ?
C21 O21 Cu1 116.07(14) . . ?
C21 O21 Cu1 138.86(14) . 2_666 ?
Cu1 O21 Cu1 104.06(7) . 2_666 ?
H31A O31 H31B 102(5) . . ?
N2 Cu1 O21 176.39(8) . . ?
N2 Cu1 O1 90.70(7) . . ?
O21 Cu1 O1 90.92(7) . . ?
N2 Cu1 N1 82.78(8) . . ?
O21 Cu1 N1 95.03(7) . . ?
O1 Cu1 N1 167.67(7) . . ?
N2 Cu1 O21 107.23(7) . 2_666 ?
O21 Cu1 O21 75.94(7) . 2_666 ?
O1 Cu1 O21 91.51(6) . 2_666 ?
N1 Cu1 O21 100.39(7) . 2_666 ?

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
N1 C1 C2 C3 -0.1(4) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 N1 -0.3(3) . . . . ?
C3 C4 C5 C6 178.8(2) . . . . ?
N1 C5 C6 N2 -7.0(3) . . . . ?
C4 C5 C6 N2 173.8(2) . . . . ?
N2 C7 C8 C9 -7.8(4) . . . . ?
N2 C7 C8 C12 177.9(2) . . . . ?
C7 C8 C9 O1 10.7(4) . . . . ?
C12 C8 C9 O1 -175.1(2) . . . . ?
C7 C8 C9 O2 -166.0(2) . . . . ?
C12 C8 C9 O2 8.1(3) . . . . ?
C7 C8 C12 O3 -160.7(2) . . . . ?
C9 C8 C12 O3 25.1(4) . . . . ?
C7 C8 C12 O4 18.4(3) . . . . ?
C9 C8 C12 O4 -155.8(2) . . . . ?
C4 C5 N1 C1 0.7(3) . . . . ?
C6 C5 N1 C1 -178.5(2) . . . . ?
C4 C5 N1 Cu1 -176.53(17) . . . . ?
C6 C5 N1 Cu1 4.3(3) . . . . ?
C2 C1 N1 C5 -0.4(3) . . . . ?
C2 C1 N1 Cu1 176.39(17) . . . . ?
C8 C7 N2 C6 178.7(2) . . . . ?
C8 C7 N2 Cu1 -3.8(3) . . . . ?
C5 C6 N2 C7 -175.61(19) . . . . ?
C5 C6 N2 Cu1 6.7(2) . . . . ?
O2 C9 O1 Cu1 174.80(15) . . . . ?
C8 C9 O1 Cu1 -1.8(3) . . . . ?
O1 C9 O2 C10 -6.6(3) . . . . ?
C8 C9 O2 C10 170.4(2) . . . . ?
C11 C10 O2 C9 -79.0(3) . . . . ?
O3 C12 O4 C13 -3.5(3) . . . . ?
C8 C12 O4 C13 177.3(2) . . . . ?
C14 C13 O4 C12 -81.0(3) . . . . ?
O22 C21 O21 Cu1 -1.3(3) . . . . ?
C22 C21 O21 Cu1 177.09(15) . . . . ?
O22 C21 O21 Cu1 164.82(16) . . . 2_666 ?
C22 C21 O21 Cu1 -16.8(3) . . . 2_666 ?

_refine_diff_density_max         0.541
_refine_diff_density_min         -0.771
_refine_diff_density_rms         0.103

####################################################################### 
# 
# 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_cl109
_database_code_depnum_ccdc_archive 'CCDC 1566634'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;


# start Validation Reply Form
_vrf_RFACR01_cl109               
;
PROBLEM: The value of the weighted R factor is > 0.35
RESPONSE: Crystal of low quality. Will only be discussed as motif.
;
_vrf_RINTA01_cl109               
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: Crystal of low quality. Will only be discussed as motif.
;
_vrf_PLAT971_cl109               
;
PROBLEM: Check Calcd Residual Density  0.92A From      I1       5.01 eA-3  
RESPONSE: Crystal of low quality. Will only be discussed as motif.
;
_vrf_PLAT972_cl109               
;
PROBLEM: Check Calcd Residual Density  0.85A From      I1      -3.97 eA-3  
RESPONSE: Crystal of low quality. Will only be discussed as motif.
;
_vrf_PLAT020_cl109               
;
PROBLEM: The value of Rint is greater than 0.12 .........      0.215 Report
RESPONSE: Crystal of low quality. Will only be discussed as motif.
;
_vrf_PLAT084_cl109               
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.36 Report
RESPONSE: Crystal of low quality. Will only be discussed as motif.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;
_chemical_name_common            '[CuL30fI]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H34 Cu2 I2 N4 O6'
_chemical_formula_sum            'C36 H34 Cu2 I2 N4 O6'
_chemical_formula_weight         999.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   10.3415(7)
_cell_length_b                   9.2060(4)
_cell_length_c                   19.3186(14)
_cell_angle_alpha                90
_cell_angle_beta                 98.818(5)
_cell_angle_gamma                90
_cell_volume                     1817.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    15019
_cell_measurement_theta_min      2.12
_cell_measurement_theta_max      28.50

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.826
_exptl_crystal_F_000             980
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    2.919
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            13816
_diffrn_reflns_av_unetI/netI     0.1235
_diffrn_reflns_av_R_equivalents  0.2146
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.111
_diffrn_reflns_theta_max         28.591
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             4329
_reflns_number_gt                3384
_reflns_threshold_expression     'I > 2σ(I)'


_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4329
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1413
_refine_ls_R_factor_gt           0.1270
_refine_ls_wR_factor_ref         0.3631
_refine_ls_wR_factor_gt          0.3393
_refine_ls_goodness_of_fit_ref   1.372
_refine_ls_restrained_S_all      1.372
_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
C1 C 0.6509(10) 0.2176(10) 0.9561(6) 0.035(2) Uani 1 1 d . . . . .
H1 H 0.7010 0.2910 0.9824 0.043 Uiso 1 1 calc R U . . .
C2 C 0.7120(9) 0.1212(11) 0.9160(6) 0.030(2) Uani 1 1 d . . . . .
H2 H 0.8029 0.1305 0.9142 0.036 Uiso 1 1 calc R U . . .
C3 C 0.6402(11) 0.0112(11) 0.8786(6) 0.035(2) Uani 1 1 d . . . . .
H3 H 0.6802 -0.0548 0.8506 0.042 Uiso 1 1 calc R U . . .
C4 C 0.5079(11) 0.0013(10) 0.8838(6) 0.037(2) Uani 1 1 d . . . . .
H4 H 0.4564 -0.0745 0.8602 0.045 Uiso 1 1 calc R U . . .
C5 C 0.4504(10) 0.1028(10) 0.9235(6) 0.030(2) Uani 1 1 d . . . . .
C6 C 0.3069(11) 0.1013(10) 0.9238(6) 0.034(2) Uani 1 1 d . . . . .
H6A H 0.2782 0.0017 0.9335 0.041 Uiso 1 1 calc R U . . .
H6B H 0.2606 0.1315 0.8774 0.041 Uiso 1 1 calc R U . . .
C7 C 0.1664(9) 0.1881(9) 1.0044(6) 0.031(2) Uani 1 1 d . . . . .
H7 H 0.1079 0.1141 0.9848 0.037 Uiso 1 1 calc R U . . .
C8 C 0.1272(9) 0.2723(9) 1.0590(6) 0.030(2) Uani 1 1 d . . . . .
C9 C 0.1946(9) 0.4018(10) 1.0822(6) 0.0292(19) Uani 1 1 d . . . . .
C10 C 0.1398(9) 0.5090(9) 1.1296(5) 0.0258(18) Uani 1 1 d . . . . .
C11 C 0.2294(11) 0.5794(10) 1.1823(6) 0.033(2) Uani 1 1 d . . . . .
H11 H 0.3193 0.5532 1.1891 0.040 Uiso 1 1 calc R U . . .
C12 C 0.1866(11) 0.6842(10) 1.2230(6) 0.036(2) Uani 1 1 d . . . . .
H12 H 0.2476 0.7330 1.2569 0.043 Uiso 1 1 calc R U . . .
C13 C 0.0559(12) 0.7204(11) 1.2157(7) 0.041(3) Uani 1 1 d . . . . .
H13 H 0.0273 0.7929 1.2449 0.050 Uiso 1 1 calc R U . . .
C14 C -0.0351(11) 0.6503(12) 1.1652(8) 0.046(3) Uani 1 1 d . . . . .
H14 H -0.1252 0.6748 1.1608 0.055 Uiso 1 1 calc R U . . .
C15 C 0.0059(10) 0.5456(11) 1.1218(7) 0.034(2) Uani 1 1 d . . . . .
H15 H -0.0554 0.4992 1.0871 0.041 Uiso 1 1 calc R U . . .
C16 C 0.0164(10) 0.2091(10) 1.0887(7) 0.037(2) Uani 1 1 d . . . . .
C17 C -0.0919(10) 0.1780(10) 1.1857(6) 0.035(2) Uani 1 1 d . . . . .
H17A H -0.0809 0.0722 1.1939 0.042 Uiso 1 1 calc R U . . .
H17B H -0.1746 0.1945 1.1534 0.042 Uiso 1 1 calc R U . . .
C18 C -0.0940(12) 0.2581(12) 1.2550(7) 0.042(2) Uani 1 1 d . . . . .
H18A H -0.0432 0.2033 1.2933 0.063 Uiso 1 1 calc R U . . .
H18B H -0.1846 0.2675 1.2636 0.063 Uiso 1 1 calc R U . . .
H18C H -0.0557 0.3550 1.2523 0.063 Uiso 1 1 calc R U . . .
Cu1 Cu 0.41745(11) 0.33342(11) 1.01530(7) 0.0306(4) Uani 1 1 d . . . . .
I1 I 0.61241(6) 0.43413(6) 1.10612(4) 0.0356(4) Uani 1 1 d . . . . .
N1 N 0.5217(8) 0.2080(8) 0.9582(5) 0.0266(16) Uani 1 1 d . . . . .
N2 N 0.2745(7) 0.2024(8) 0.9786(5) 0.0278(17) Uani 1 1 d . . . . .
O1 O 0.3013(8) 0.4422(7) 1.0648(5) 0.0361(18) Uani 1 1 d . . . . .
O2 O -0.0648(7) 0.1299(9) 1.0553(5) 0.0408(19) Uani 1 1 d . . . . .
O3 O 0.0185(7) 0.2365(8) 1.1561(4) 0.0329(15) 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
C1 N1 1.346(13) . ?
C1 C2 1.392(14) . ?
C1 H1 0.9500 . ?
C2 C3 1.391(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.399(16) . ?
C4 H4 0.9500 . ?
C5 N1 1.333(12) . ?
C5 C6 1.484(15) . ?
C6 N2 1.486(13) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.298(12) . ?
C7 C8 1.417(14) . ?
C7 H7 0.9500 . ?
C8 C9 1.419(12) . ?
C8 C16 1.478(14) . ?
C9 O1 1.258(13) . ?
C9 C10 1.512(13) . ?
C10 C15 1.411(14) . ?
C10 C11 1.424(13) . ?
C11 C12 1.360(15) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.404(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(17) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 O2 1.219(12) . ?
C16 O3 1.323(15) . ?
C17 O3 1.456(12) . ?
C17 C18 1.532(16) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
Cu1 O1 1.927(8) . ?
Cu1 N2 1.955(8) . ?
Cu1 N1 2.020(8) . ?
Cu1 I1 2.6303(14) . ?

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
N1 C1 C2 120.8(9) . . ?
N1 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 120.1(9) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 117.7(9) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C3 C4 C5 120.1(9) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 120.8(10) . . ?
N1 C5 C6 118.7(9) . . ?
C4 C5 C6 120.4(9) . . ?
C5 C6 N2 109.4(8) . . ?
C5 C6 H6A 109.8 . . ?
N2 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
N2 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 126.2(9) . . ?
N2 C7 H7 116.9 . . ?
C8 C7 H7 116.9 . . ?
C7 C8 C9 120.9(9) . . ?
C7 C8 C16 113.6(8) . . ?
C9 C8 C16 125.5(10) . . ?
O1 C9 C8 124.8(9) . . ?
O1 C9 C10 113.2(8) . . ?
C8 C9 C10 121.9(9) . . ?
C15 C10 C11 119.2(9) . . ?
C15 C10 C9 122.9(9) . . ?
C11 C10 C9 117.9(9) . . ?
C12 C11 C10 120.2(10) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.9(10) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C14 120.1(10) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 120.4(10) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C10 119.2(10) . . ?
C14 C15 H15 120.4 . . ?
C10 C15 H15 120.4 . . ?
O2 C16 O3 122.7(10) . . ?
O2 C16 C8 122.8(12) . . ?
O3 C16 C8 114.2(8) . . ?
O3 C17 C18 106.4(8) . . ?
O3 C17 H17A 110.5 . . ?
C18 C17 H17A 110.5 . . ?
O3 C17 H17B 110.5 . . ?
C18 C17 H17B 110.5 . . ?
H17A C17 H17B 108.6 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 Cu1 N2 90.3(3) . . ?
O1 Cu1 N1 173.7(3) . . ?
N2 Cu1 N1 83.5(3) . . ?
O1 Cu1 I1 87.6(2) . . ?
N2 Cu1 I1 156.8(3) . . ?
N1 Cu1 I1 98.5(2) . . ?
C5 N1 C1 120.5(9) . . ?
C5 N1 Cu1 112.9(7) . . ?
C1 N1 Cu1 126.4(7) . . ?
C7 N2 C6 120.8(8) . . ?
C7 N2 Cu1 124.9(7) . . ?
C6 N2 Cu1 113.8(6) . . ?
C9 O1 Cu1 128.2(6) . . ?
C16 O3 C17 114.9(8) . . ?

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
N1 C1 C2 C3 -1.5(16) . . . . ?
C1 C2 C3 C4 -0.7(15) . . . . ?
C2 C3 C4 C5 2.2(16) . . . . ?
C3 C4 C5 N1 -1.6(15) . . . . ?
C3 C4 C5 C6 174.3(10) . . . . ?
N1 C5 C6 N2 -13.5(12) . . . . ?
C4 C5 C6 N2 170.6(9) . . . . ?
N2 C7 C8 C9 12.2(16) . . . . ?
N2 C7 C8 C16 -165.9(10) . . . . ?
C7 C8 C9 O1 -10.1(16) . . . . ?
C16 C8 C9 O1 167.7(10) . . . . ?
C7 C8 C9 C10 167.6(9) . . . . ?
C16 C8 C9 C10 -14.6(15) . . . . ?
O1 C9 C10 C15 138.0(10) . . . . ?
C8 C9 C10 C15 -40.0(15) . . . . ?
O1 C9 C10 C11 -39.4(13) . . . . ?
C8 C9 C10 C11 142.6(10) . . . . ?
C15 C10 C11 C12 -2.2(15) . . . . ?
C9 C10 C11 C12 175.3(9) . . . . ?
C10 C11 C12 C13 2.3(16) . . . . ?
C11 C12 C13 C14 -0.8(18) . . . . ?
C12 C13 C14 C15 -0.8(19) . . . . ?
C13 C14 C15 C10 0.9(18) . . . . ?
C11 C10 C15 C14 0.6(15) . . . . ?
C9 C10 C15 C14 -176.8(10) . . . . ?
C7 C8 C16 O2 -27.0(14) . . . . ?
C9 C8 C16 O2 155.0(10) . . . . ?
C7 C8 C16 O3 148.0(9) . . . . ?
C9 C8 C16 O3 -30.0(14) . . . . ?
C4 C5 N1 C1 -0.7(14) . . . . ?
C6 C5 N1 C1 -176.6(9) . . . . ?
C4 C5 N1 Cu1 -177.0(7) . . . . ?
C6 C5 N1 Cu1 7.1(11) . . . . ?
C2 C1 N1 C5 2.2(15) . . . . ?
C2 C1 N1 Cu1 178.0(7) . . . . ?
C8 C7 N2 C6 176.7(9) . . . . ?
C8 C7 N2 Cu1 5.9(15) . . . . ?
C5 C6 N2 C7 -158.2(9) . . . . ?
C5 C6 N2 Cu1 13.5(10) . . . . ?
C8 C9 O1 Cu1 -10.4(16) . . . . ?
C10 C9 O1 Cu1 171.7(7) . . . . ?
O2 C16 O3 C17 -6.5(13) . . . . ?
C8 C16 O3 C17 178.5(8) . . . . ?
C18 C17 O3 C16 -163.1(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 I1 0.95 2.99 3.589(11) 122.1 .
C1 H1 O1 0.95 2.62 3.206(11) 120.4 3_667
C6 H6A O2 0.99 2.56 3.358(12) 138.0 3_557
C7 H7 O2 0.95 2.40 3.260(11) 151.3 3_557
C17 H17B I1 0.99 3.15 3.979(11) 142.0 1_455
C18 H18A I1 0.98 3.29 4.036(12) 133.9 2_547

_refine_diff_density_max         5.023
_refine_diff_density_min         -3.877
_refine_diff_density_rms         0.430

####################################################################### 
# 
# 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_cl117
_database_code_depnum_ccdc_archive 'CCDC 1566619'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;
_chemical_name_common            '[CuL30aNO3]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H30 Cu2 N6 O12'
_chemical_formula_sum            'C26 H30 Cu2 N6 O12'
_chemical_formula_weight         745.64

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                   12.7796(5)
_cell_length_b                   13.8977(8)
_cell_length_c                   16.9969(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.798(3)
_cell_angle_gamma                90
_cell_volume                     2904.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    10957
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      26.62

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_F_000             1528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.118
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.088
_exptl_absorpt_coefficient_mu    1.540
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;??
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            9232
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.211
_diffrn_reflns_theta_max         28.459
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3429
_reflns_number_gt                2893
_reflns_threshold_expression     'I > 2σ(I)'

_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3429
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0766
_refine_ls_wR_factor_gt          0.0670
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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
C1 C -0.23095(14) 0.11596(13) 0.12595(11) 0.0194(3) Uani 1 1 d . . . . .
H1 H -0.2096 0.1129 0.1840 0.023 Uiso 1 1 calc R U . . .
C2 C -0.34035(15) 0.11983(14) 0.08552(11) 0.0217(4) Uani 1 1 d . . . . .
H2 H -0.3935 0.1191 0.1152 0.026 Uiso 1 1 calc R U . . .
C3 C -0.37134(15) 0.12476(14) 0.00062(11) 0.0222(4) Uani 1 1 d . . . . .
H3 H -0.4461 0.1269 -0.0287 0.027 Uiso 1 1 calc R U . . .
C4 C -0.29221(14) 0.12646(13) -0.04045(11) 0.0191(3) Uani 1 1 d . . . . .
H4 H -0.3117 0.1303 -0.0984 0.023 Uiso 1 1 calc R U . . .
C5 C -0.18369(14) 0.12252(12) 0.00386(10) 0.0149(3) Uani 1 1 d . . . . .
C6 C -0.09347(14) 0.12501(12) -0.03720(10) 0.0163(3) Uani 1 1 d . . . . .
H6A H -0.0993 0.0686 -0.0737 0.020 Uiso 1 1 calc R U . . .
H6B H -0.0996 0.1840 -0.0709 0.020 Uiso 1 1 calc R U . . .
C7 C 0.09846(14) 0.12916(11) -0.00114(10) 0.0144(3) Uani 1 1 d . . . . .
H7 H 0.0877 0.1370 -0.0583 0.017 Uiso 1 1 calc R U . . .
C8 C 0.20814(14) 0.12453(12) 0.04799(10) 0.0156(3) Uani 1 1 d . . . . .
C9 C 0.23434(14) 0.11293(12) 0.13322(11) 0.0179(3) Uani 1 1 d . . . . .
C10 C 0.35008(16) 0.10228(17) 0.18498(12) 0.0285(4) Uani 1 1 d . . . . .
H10A H 0.3504 0.0870 0.2413 0.043 Uiso 1 1 calc R U . . .
H10B H 0.3894 0.1626 0.1842 0.043 Uiso 1 1 calc R U . . .
H10C H 0.3857 0.0503 0.1631 0.043 Uiso 1 1 calc R U . . .
C11 C 0.29389(14) 0.13015(12) 0.00478(10) 0.0168(3) Uani 1 1 d . . . . .
C12 C 0.32474(15) 0.13563(14) -0.12714(11) 0.0210(4) Uani 1 1 d . . . . .
H12A H 0.3783 0.0825 -0.1184 0.025 Uiso 1 1 calc R U . . .
H12B H 0.3644 0.1973 -0.1138 0.025 Uiso 1 1 calc R U . . .
C13 C 0.25476(18) 0.13612(18) -0.21440(12) 0.0309(5) Uani 1 1 d . . . . .
H13A H 0.2207 0.0729 -0.2280 0.046 Uiso 1 1 calc R U . . .
H13B H 0.3000 0.1504 -0.2512 0.046 Uiso 1 1 calc R U . . .
H13C H 0.1982 0.1854 -0.2207 0.046 Uiso 1 1 calc R U . . .
N1 N -0.15341(12) 0.11641(10) 0.08567(8) 0.0148(3) Uani 1 1 d . . . . .
N2 N 0.01174(12) 0.12374(10) 0.02450(8) 0.0153(3) Uani 1 1 d . . . . .
N11 N 0.0000 -0.02728(16) 0.2500 0.0185(4) Uani 1 2 d S T P . .
N21 N 0.0000 0.31056(16) 0.2500 0.0213(4) Uani 1 2 d S T P . .
O1 O 0.16265(10) 0.10883(9) 0.17316(7) 0.0202(3) Uani 1 1 d . . . . .
O2 O 0.39033(11) 0.14130(11) 0.03493(8) 0.0253(3) Uani 1 1 d . . . . .
O3 O 0.25070(10) 0.12214(10) -0.07672(8) 0.0208(3) Uani 1 1 d . . . . .
O11 O 0.0000 0.06850(12) 0.2500 0.0183(3) Uani 1 2 d S T P . .
O12 O 0.00113(11) -0.06638(10) 0.18629(7) 0.0249(3) Uani 1 1 d . . . . .
O21 O -0.02344(12) 0.26686(10) 0.18344(8) 0.0276(3) Uani 1 1 d . . . . .
O22 O 0.0000 0.39964(14) 0.2500 0.0324(5) Uani 1 2 d S T P . .
Cu1 Cu 0.00650(2) 0.11532(2) 0.13570(2) 0.01463(8) 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
C1 N1 1.349(2) . ?
C1 C2 1.381(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.390(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(2) . ?
C4 H4 0.9500 . ?
C5 N1 1.341(2) . ?
C5 C6 1.502(2) . ?
C6 N2 1.463(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.299(2) . ?
C7 C8 1.424(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.404(2) . ?
C8 C11 1.478(2) . ?
C9 O1 1.281(2) . ?
C9 C10 1.508(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O2 1.209(2) . ?
C11 O3 1.349(2) . ?
C12 O3 1.451(2) . ?
C12 C13 1.509(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N1 Cu1 1.9883(14) . ?
N2 Cu1 1.9130(14) . ?
N11 O12 1.2152(16) . ?
N11 O12 1.2152(16) 2 ?
N11 O11 1.331(3) . ?
N21 O22 1.238(3) . ?
N21 O21 1.2465(17) 2 ?
N21 O21 1.2465(17) . ?
O1 Cu1 1.9245(13) . ?
O11 Cu1 2.0718(6) . ?
O11 Cu1 2.0718(6) 2 ?
O21 Cu1 2.3258(14) . ?

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
N1 C1 C2 122.09(16) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C1 C2 C3 118.83(17) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 119.10(17) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 119.19(16) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 121.95(15) . . ?
N1 C5 C6 116.24(15) . . ?
C4 C5 C6 121.81(15) . . ?
N2 C6 C5 109.79(13) . . ?
N2 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 126.44(15) . . ?
N2 C7 H7 116.8 . . ?
C8 C7 H7 116.8 . . ?
C9 C8 C7 122.02(15) . . ?
C9 C8 C11 121.19(15) . . ?
C7 C8 C11 116.78(14) . . ?
O1 C9 C8 123.19(16) . . ?
O1 C9 C10 114.56(15) . . ?
C8 C9 C10 122.24(16) . . ?
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 . . ?
O2 C11 O3 122.05(15) . . ?
O2 C11 C8 127.17(16) . . ?
O3 C11 C8 110.77(14) . . ?
O3 C12 C13 105.88(15) . . ?
O3 C12 H12A 110.6 . . ?
C13 C12 H12A 110.6 . . ?
O3 C12 H12B 110.6 . . ?
C13 C12 H12B 110.6 . . ?
H12A C12 H12B 108.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 N1 C1 118.83(15) . . ?
C5 N1 Cu1 114.64(11) . . ?
C1 N1 Cu1 126.46(12) . . ?
C7 N2 C6 117.42(14) . . ?
C7 N2 Cu1 126.70(12) . . ?
C6 N2 Cu1 115.88(11) . . ?
O12 N11 O12 126.9(2) . 2 ?
O12 N11 O11 116.56(12) . . ?
O12 N11 O11 116.56(12) 2 . ?
O22 N21 O21 119.15(11) . 2 ?
O22 N21 O21 119.16(11) . . ?
O21 N21 O21 121.7(2) 2 . ?
C9 O1 Cu1 130.48(12) . . ?
C11 O3 C12 116.45(14) . . ?
N11 O11 Cu1 108.30(5) . . ?
N11 O11 Cu1 108.30(5) . 2 ?
Cu1 O11 Cu1 143.39(9) . 2 ?
N21 O21 Cu1 137.40(13) . . ?
N2 Cu1 O1 91.01(6) . . ?
N2 Cu1 N1 83.42(6) . . ?
O1 Cu1 N1 173.86(5) . . ?
N2 Cu1 O11 165.20(6) . . ?
O1 Cu1 O11 88.72(4) . . ?
N1 Cu1 O11 96.00(4) . . ?
N2 Cu1 O21 110.04(5) . . ?
O1 Cu1 O21 100.44(5) . . ?
N1 Cu1 O21 83.96(5) . . ?
O11 Cu1 O21 84.54(6) . . ?

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
N1 C1 C2 C3 -0.3(3) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 N1 0.5(3) . . . . ?
C3 C4 C5 C6 -179.43(16) . . . . ?
N1 C5 C6 N2 -2.2(2) . . . . ?
C4 C5 C6 N2 177.73(15) . . . . ?
N2 C7 C8 C9 0.1(3) . . . . ?
N2 C7 C8 C11 178.65(15) . . . . ?
C7 C8 C9 O1 -2.3(3) . . . . ?
C11 C8 C9 O1 179.18(16) . . . . ?
C7 C8 C9 C10 176.42(17) . . . . ?
C11 C8 C9 C10 -2.1(3) . . . . ?
C9 C8 C11 O2 -12.8(3) . . . . ?
C7 C8 C11 O2 168.61(17) . . . . ?
C9 C8 C11 O3 167.90(15) . . . . ?
C7 C8 C11 O3 -10.7(2) . . . . ?
C4 C5 N1 C1 -1.3(2) . . . . ?
C6 C5 N1 C1 178.62(15) . . . . ?
C4 C5 N1 Cu1 -178.41(13) . . . . ?
C6 C5 N1 Cu1 1.50(18) . . . . ?
C2 C1 N1 C5 1.2(3) . . . . ?
C2 C1 N1 Cu1 177.94(13) . . . . ?
C8 C7 N2 C6 -176.81(15) . . . . ?
C8 C7 N2 Cu1 3.8(2) . . . . ?
C5 C6 N2 C7 -177.55(14) . . . . ?
C5 C6 N2 Cu1 1.91(17) . . . . ?
C8 C9 O1 Cu1 0.5(3) . . . . ?
C10 C9 O1 Cu1 -178.34(13) . . . . ?
O2 C11 O3 C12 -5.0(2) . . . . ?
C8 C11 O3 C12 174.34(14) . . . . ?
C13 C12 O3 C11 -172.77(16) . . . . ?
O12 N11 O11 Cu1 -1.60(7) . . . . ?
O12 N11 O11 Cu1 178.41(7) 2 . . . ?
O12 N11 O11 Cu1 178.40(7) . . . 2 ?
O12 N11 O11 Cu1 -1.59(7) 2 . . 2 ?
O22 N21 O21 Cu1 157.70(10) . . . . ?
O21 N21 O21 Cu1 -22.30(10) 2 . . . ?

_refine_diff_density_max         0.830
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.091

####################################################################### 
# 
# 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_cl128
_database_code_depnum_ccdc_archive 'CCDC 1566635'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;
_chemical_name_common            '[CuL30aSCN]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 Cu N3 O3 S'
_chemical_formula_sum            'C14 H15 Cu N3 O3 S'
_chemical_formula_weight         368.89

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'
S S 0.1246 0.1234 '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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   5.9027(5)
_cell_length_b                   16.4411(12)
_cell_length_c                   15.7542(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.344(6)
_cell_angle_gamma                90
_cell_volume                     1512.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    5708
_cell_measurement_theta_min      1.82
_cell_measurement_theta_max      28.49

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_F_000             756
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.112
_exptl_crystal_size_mid          0.051
_exptl_crystal_size_min          0.045
_exptl_absorpt_coefficient_mu    1.597
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            8001
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.800
_diffrn_reflns_theta_max         28.519
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3520
_reflns_number_gt                2615
_reflns_threshold_expression     'I > 2σ(I)'


_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0233P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3520
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0632
_refine_ls_wR_factor_gt          0.0590
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_restrained_S_all      0.894
_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
C1 C 0.3073(4) 0.20742(16) 0.66983(14) 0.0222(5) Uani 1 1 d . . . . .
H1 H 0.1693 0.2353 0.6493 0.027 Uiso 1 1 calc R U . . .
C2 C 0.3847(4) 0.20796(17) 0.75667(15) 0.0266(5) Uani 1 1 d . . . . .
H2 H 0.3018 0.2356 0.7953 0.032 Uiso 1 1 calc R U . . .
C3 C 0.5868(4) 0.16717(17) 0.78638(14) 0.0263(5) Uani 1 1 d . . . . .
H3 H 0.6451 0.1668 0.8458 0.032 Uiso 1 1 calc R U . . .
C4 C 0.7017(4) 0.12718(16) 0.72844(14) 0.0223(5) Uani 1 1 d . . . . .
H4 H 0.8403 0.0990 0.7475 0.027 Uiso 1 1 calc R U . . .
C5 C 0.6126(3) 0.12866(15) 0.64207(13) 0.0181(4) Uani 1 1 d . . . . .
C6 C 0.7274(3) 0.08542(15) 0.57542(13) 0.0186(5) Uani 1 1 d . . . . .
H6A H 0.8859 0.1057 0.5774 0.022 Uiso 1 1 calc R U . . .
H6B H 0.7343 0.0263 0.5877 0.022 Uiso 1 1 calc R U . . .
C7 C 0.6801(3) 0.07081(15) 0.42420(14) 0.0181(5) Uani 1 1 d . . . . .
H7 H 0.8180 0.0404 0.4359 0.022 Uiso 1 1 calc R U . . .
C8 C 0.5859(3) 0.07958(15) 0.33648(13) 0.0183(5) Uani 1 1 d . . . . .
C9 C 0.3765(3) 0.11971(15) 0.31038(14) 0.0196(5) Uani 1 1 d . . . . .
C10 C 0.2636(4) 0.12646(19) 0.21850(15) 0.0291(6) Uani 1 1 d . . . . .
H10A H 0.1028 0.1420 0.2171 0.044 Uiso 1 1 calc R U . . .
H10B H 0.2720 0.0739 0.1898 0.044 Uiso 1 1 calc R U . . .
H10C H 0.3425 0.1679 0.1889 0.044 Uiso 1 1 calc R U . . .
C11 C 0.7182(3) 0.03666(15) 0.27789(14) 0.0199(5) Uani 1 1 d . . . . .
C12 C 0.7628(4) 0.01071(17) 0.13231(14) 0.0250(5) Uani 1 1 d . . . . .
H12A H 0.6817 -0.0420 0.1240 0.030 Uiso 1 1 calc R U . . .
H12B H 0.9276 0.0001 0.1510 0.030 Uiso 1 1 calc R U . . .
C13 C 0.7288(4) 0.05943(18) 0.05064(15) 0.0301(6) Uani 1 1 d . . . . .
H13A H 0.5659 0.0722 0.0350 0.045 Uiso 1 1 calc R U . . .
H13B H 0.7817 0.0278 0.0046 0.045 Uiso 1 1 calc R U . . .
H13C H 0.8166 0.1101 0.0592 0.045 Uiso 1 1 calc R U . . .
C21 C -0.1202(3) 0.26357(15) 0.47809(13) 0.0184(5) Uani 1 1 d . . . . .
N1 N 0.4193(3) 0.16895(13) 0.61302(11) 0.0176(4) Uani 1 1 d . . . . .
N2 N 0.5985(3) 0.09969(12) 0.48986(11) 0.0165(4) Uani 1 1 d . . . . .
N21 N 0.0558(3) 0.23074(13) 0.48410(12) 0.0216(4) Uani 1 1 d . . . . .
O1 O 0.2623(2) 0.15358(11) 0.36332(10) 0.0238(4) Uani 1 1 d . . . . .
O2 O 0.8621(3) -0.01504(12) 0.30123(10) 0.0289(4) Uani 1 1 d . . . . .
O3 O 0.6686(3) 0.05971(11) 0.19562(10) 0.0241(4) Uani 1 1 d . . . . .
S21 S -0.36600(9) 0.30997(4) 0.47018(4) 0.02479(14) Uani 1 1 d . . . . .
Cu1 Cu 0.33946(4) 0.17064(2) 0.48527(2) 0.01741(8) 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
C1 N1 1.345(3) . ?
C1 C2 1.378(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.341(3) . ?
C5 C6 1.508(3) . ?
C6 N2 1.467(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.293(3) . ?
C7 C8 1.420(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.409(3) . ?
C8 C11 1.473(3) . ?
C9 O1 1.274(3) . ?
C9 C10 1.507(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O2 1.220(3) . ?
C11 O3 1.341(3) . ?
C12 O3 1.454(3) . ?
C12 C13 1.504(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C21 N21 1.163(3) . ?
C21 S21 1.628(2) . ?
N1 Cu1 1.9995(17) . ?
N2 Cu1 1.9161(18) . ?
N21 Cu1 1.9419(19) . ?
O1 Cu1 1.9296(15) . ?

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
N1 C1 C2 122.6(2) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C1 C2 C3 118.4(2) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 119.2(2) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 119.2(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 121.8(2) . . ?
N1 C5 C6 116.18(18) . . ?
C4 C5 C6 122.05(19) . . ?
N2 C6 C5 109.82(17) . . ?
N2 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 127.0(2) . . ?
N2 C7 H7 116.5 . . ?
C8 C7 H7 116.5 . . ?
C9 C8 C7 122.32(19) . . ?
C9 C8 C11 124.34(19) . . ?
C7 C8 C11 113.14(18) . . ?
O1 C9 C8 122.60(19) . . ?
O1 C9 C10 113.24(18) . . ?
C8 C9 C10 124.2(2) . . ?
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 . . ?
O2 C11 O3 122.2(2) . . ?
O2 C11 C8 123.7(2) . . ?
O3 C11 C8 114.14(19) . . ?
O3 C12 C13 106.0(2) . . ?
O3 C12 H12A 110.5 . . ?
C13 C12 H12A 110.5 . . ?
O3 C12 H12B 110.5 . . ?
C13 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N21 C21 S21 179.6(2) . . ?
C5 N1 C1 118.76(18) . . ?
C5 N1 Cu1 114.52(14) . . ?
C1 N1 Cu1 126.60(15) . . ?
C7 N2 C6 118.20(17) . . ?
C7 N2 Cu1 125.53(15) . . ?
C6 N2 Cu1 115.88(13) . . ?
C21 N21 Cu1 175.03(19) . . ?
C9 O1 Cu1 130.14(14) . . ?
C11 O3 C12 117.04(18) . . ?
N2 Cu1 O1 91.19(7) . . ?
N2 Cu1 N21 172.88(9) . . ?
O1 Cu1 N21 89.20(7) . . ?
N2 Cu1 N1 83.30(7) . . ?
O1 Cu1 N1 170.84(8) . . ?
N21 Cu1 N1 95.37(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.1(4) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 N1 1.0(4) . . . . ?
C3 C4 C5 C6 -179.2(2) . . . . ?
N1 C5 C6 N2 1.5(3) . . . . ?
C4 C5 C6 N2 -178.3(2) . . . . ?
N2 C7 C8 C9 -3.1(4) . . . . ?
N2 C7 C8 C11 -178.1(2) . . . . ?
C7 C8 C9 O1 2.9(4) . . . . ?
C11 C8 C9 O1 177.2(2) . . . . ?
C7 C8 C9 C10 -176.5(2) . . . . ?
C11 C8 C9 C10 -2.1(4) . . . . ?
C9 C8 C11 O2 -159.7(2) . . . . ?
C7 C8 C11 O2 15.1(3) . . . . ?
C9 C8 C11 O3 20.8(3) . . . . ?
C7 C8 C11 O3 -164.4(2) . . . . ?
C4 C5 N1 C1 -1.4(3) . . . . ?
C6 C5 N1 C1 178.8(2) . . . . ?
C4 C5 N1 Cu1 174.82(18) . . . . ?
C6 C5 N1 Cu1 -5.0(3) . . . . ?
C2 C1 N1 C5 0.8(4) . . . . ?
C2 C1 N1 Cu1 -174.89(19) . . . . ?
C8 C7 N2 C6 -178.2(2) . . . . ?
C8 C7 N2 Cu1 -5.7(3) . . . . ?
C5 C6 N2 C7 176.1(2) . . . . ?
C5 C6 N2 Cu1 2.9(2) . . . . ?
C8 C9 O1 Cu1 6.5(3) . . . . ?
C10 C9 O1 Cu1 -174.12(17) . . . . ?
O2 C11 O3 C12 10.8(3) . . . . ?
C8 C11 O3 C12 -169.76(19) . . . . ?
C13 C12 O3 C11 -167.30(19) . . . . ?

_refine_diff_density_max         0.377
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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_cl099
_database_code_depnum_ccdc_archive 'CCDC 1566633'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;
_chemical_name_common            '[CuL30aI]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H30 Cu2 I2 N4 O6'
_chemical_formula_sum            'C13 H15 Cu I N2 O3'
_chemical_formula_weight         437.71

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'
I I -0.4742 1.8119 '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                   7.8179(3)
_cell_length_b                   14.6683(6)
_cell_length_c                   13.0905(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.391(3)
_cell_angle_gamma                90
_cell_volume                     1499.85(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    8349
_cell_measurement_theta_min      2.08
_cell_measurement_theta_max      27.62

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.938
_exptl_crystal_F_000             852
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.101
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.063
_exptl_absorpt_coefficient_mu    3.522
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            9126
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.086
_diffrn_reflns_theta_max         28.465
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             3516
_reflns_number_gt                2940
_reflns_threshold_expression     'I > 2σ(I)'


_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0209P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3516
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0205
_refine_ls_wR_factor_ref         0.0468
_refine_ls_wR_factor_gt          0.0458
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_restrained_S_all      0.936
_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
C1 C 0.6476(3) 0.36402(18) 0.33048(19) 0.0248(5) Uani 1 1 d . . . . .
H1 H 0.5881 0.4148 0.3013 0.030 Uiso 1 1 calc R U . . .
C2 C 0.6365(3) 0.28141(19) 0.2809(2) 0.0275(6) Uani 1 1 d . . . . .
H2 H 0.5725 0.2759 0.2179 0.033 Uiso 1 1 calc R U . . .
C3 C 0.7196(3) 0.20630(19) 0.3239(2) 0.0253(5) Uani 1 1 d . . . . .
H3 H 0.7104 0.1481 0.2922 0.030 Uiso 1 1 calc R U . . .
C4 C 0.8163(3) 0.21782(17) 0.41384(19) 0.0227(5) Uani 1 1 d . . . . .
H4 H 0.8766 0.1679 0.4443 0.027 Uiso 1 1 calc R U . . .
C5 C 0.8239(3) 0.30353(16) 0.45894(17) 0.0178(5) Uani 1 1 d . . . . .
C6 C 0.9278(3) 0.31923(17) 0.55632(18) 0.0225(5) Uani 1 1 d . . . . .
H6A H 0.8947 0.2745 0.6085 0.027 Uiso 1 1 calc R U . . .
H6B H 1.0508 0.3107 0.5440 0.027 Uiso 1 1 calc R U . . .
C7 C 0.9711(3) 0.43346(16) 0.68151(18) 0.0176(4) Uani 1 1 d . . . . .
H7 H 1.0402 0.3883 0.7150 0.021 Uiso 1 1 calc R U . . .
C8 C 0.9566(3) 0.51849(16) 0.73239(17) 0.0185(5) Uani 1 1 d . . . . .
C9 C 0.8580(3) 0.59057(16) 0.68927(18) 0.0201(5) Uani 1 1 d . . . . .
C10 C 0.8402(4) 0.68153(18) 0.7409(2) 0.0285(6) Uani 1 1 d . . . . .
H10A H 0.7604 0.7199 0.7002 0.043 Uiso 1 1 calc R U . . .
H10B H 0.9523 0.7114 0.7469 0.043 Uiso 1 1 calc R U . . .
H10C H 0.7962 0.6726 0.8092 0.043 Uiso 1 1 calc R U . . .
C11 C 1.0560(3) 0.53106(17) 0.82874(19) 0.0229(5) Uani 1 1 d . . . . .
C12 C 1.2489(4) 0.4611(2) 0.9497(2) 0.0319(6) Uani 1 1 d . . . . .
H12A H 1.1857 0.4804 1.0100 0.038 Uiso 1 1 calc R U . . .
H12B H 1.3383 0.5070 0.9370 0.038 Uiso 1 1 calc R U . . .
C13 C 1.3283(4) 0.3699(2) 0.9681(2) 0.0383(7) Uani 1 1 d . . . . .
H13A H 1.2399 0.3262 0.9864 0.057 Uiso 1 1 calc R U . . .
H13B H 1.4150 0.3742 1.0242 0.057 Uiso 1 1 calc R U . . .
H13C H 1.3823 0.3493 0.9060 0.057 Uiso 1 1 calc R U . . .
N1 N 0.7396(3) 0.37553(14) 0.41891(15) 0.0190(4) Uani 1 1 d . . . . .
N2 N 0.8990(2) 0.41143(13) 0.59341(15) 0.0185(4) Uani 1 1 d . . . . .
O1 O 0.7763(2) 0.58522(12) 0.60334(13) 0.0252(4) Uani 1 1 d . . . . .
O2 O 1.0724(3) 0.60075(14) 0.87705(15) 0.0385(5) Uani 1 1 d . . . . .
O3 O 1.1329(2) 0.45267(12) 0.86111(13) 0.0258(4) Uani 1 1 d . . . . .
Cu1 Cu 0.74666(4) 0.48585(2) 0.50892(2) 0.01866(7) Uani 1 1 d . . . . .
I1 I 0.58207(2) 0.59839(2) 0.38453(2) 0.02191(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
C1 N1 1.348(3) . ?
C1 C2 1.376(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.387(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.340(3) . ?
C5 C6 1.500(3) . ?
C6 N2 1.458(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.303(3) . ?
C7 C8 1.421(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.412(3) . ?
C8 C11 1.465(3) . ?
C9 O1 1.272(3) . ?
C9 C10 1.505(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O2 1.206(3) . ?
C11 O3 1.357(3) . ?
C12 O3 1.447(3) . ?
C12 C13 1.490(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N1 Cu1 2.001(2) . ?
N2 Cu1 1.9298(19) . ?
O1 Cu1 1.9189(17) . ?
Cu1 I1 2.6186(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.4(2) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 119.3(2) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 118.6(2) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 119.0(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 122.4(2) . . ?
N1 C5 C6 116.8(2) . . ?
C4 C5 C6 120.8(2) . . ?
N2 C6 C5 109.87(19) . . ?
N2 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 126.3(2) . . ?
N2 C7 H7 116.8 . . ?
C8 C7 H7 116.8 . . ?
C9 C8 C7 121.5(2) . . ?
C9 C8 C11 120.7(2) . . ?
C7 C8 C11 117.6(2) . . ?
O1 C9 C8 123.5(2) . . ?
O1 C9 C10 113.5(2) . . ?
C8 C9 C10 122.9(2) . . ?
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 . . ?
O2 C11 O3 121.2(2) . . ?
O2 C11 C8 126.8(2) . . ?
O3 C11 C8 112.0(2) . . ?
O3 C12 C13 107.2(2) . . ?
O3 C12 H12A 110.3 . . ?
C13 C12 H12A 110.3 . . ?
O3 C12 H12B 110.3 . . ?
C13 C12 H12B 110.3 . . ?
H12A C12 H12B 108.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 N1 C1 118.3(2) . . ?
C5 N1 Cu1 113.96(15) . . ?
C1 N1 Cu1 127.41(17) . . ?
C7 N2 C6 117.25(19) . . ?
C7 N2 Cu1 126.93(17) . . ?
C6 N2 Cu1 115.73(14) . . ?
C9 O1 Cu1 131.22(16) . . ?
C11 O3 C12 115.6(2) . . ?
O1 Cu1 N2 90.31(8) . . ?
O1 Cu1 N1 173.28(8) . . ?
N2 Cu1 N1 83.18(8) . . ?
O1 Cu1 I1 87.98(5) . . ?
N2 Cu1 I1 171.32(6) . . ?
N1 Cu1 I1 98.22(6) . . ?

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
N1 C1 C2 C3 1.4(4) . . . . ?
C1 C2 C3 C4 -2.3(4) . . . . ?
C2 C3 C4 C5 1.3(4) . . . . ?
C3 C4 C5 N1 0.6(4) . . . . ?
C3 C4 C5 C6 -179.8(2) . . . . ?
N1 C5 C6 N2 6.0(3) . . . . ?
C4 C5 C6 N2 -173.6(2) . . . . ?
N2 C7 C8 C9 -0.3(4) . . . . ?
N2 C7 C8 C11 -176.7(2) . . . . ?
C7 C8 C9 O1 -0.1(4) . . . . ?
C11 C8 C9 O1 176.2(2) . . . . ?
C7 C8 C9 C10 -179.8(2) . . . . ?
C11 C8 C9 C10 -3.6(4) . . . . ?
C9 C8 C11 O2 -4.0(4) . . . . ?
C7 C8 C11 O2 172.4(3) . . . . ?
C9 C8 C11 O3 176.0(2) . . . . ?
C7 C8 C11 O3 -7.6(3) . . . . ?
C4 C5 N1 C1 -1.5(4) . . . . ?
C6 C5 N1 C1 178.9(2) . . . . ?
C4 C5 N1 Cu1 171.99(19) . . . . ?
C6 C5 N1 Cu1 -7.6(3) . . . . ?
C2 C1 N1 C5 0.5(4) . . . . ?
C2 C1 N1 Cu1 -172.0(2) . . . . ?
C8 C7 N2 C6 -178.5(2) . . . . ?
C8 C7 N2 Cu1 -2.1(4) . . . . ?
C5 C6 N2 C7 175.3(2) . . . . ?
C5 C6 N2 Cu1 -1.5(3) . . . . ?
C8 C9 O1 Cu1 3.1(4) . . . . ?
C10 C9 O1 Cu1 -177.15(18) . . . . ?
O2 C11 O3 C12 -6.6(4) . . . . ?
C8 C11 O3 C12 173.5(2) . . . . ?
C13 C12 O3 C11 -176.1(2) . . . . ?

_refine_diff_density_max         0.502
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.091

####################################################################### 
# 
# 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_cl083
_database_code_depnum_ccdc_archive 'CCDC 1566618'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;
_chemical_name_common            '[CuL30iOAc]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H32 Cu2 N4 O10, 4(H2 O)'
_chemical_formula_sum            'C28 H40 Cu2 N4 O14'
_chemical_formula_weight         783.72

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   8.7017(4)
_cell_length_b                   18.0339(11)
_cell_length_c                   21.7086(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3406.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    5354
_cell_measurement_theta_min      1.88
_cell_measurement_theta_max      28.46

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_F_000             1624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.048
_exptl_absorpt_coefficient_mu    1.320
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;??
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            17827
_diffrn_reflns_av_unetI/netI     0.1058
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.876
_diffrn_reflns_theta_max         28.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4130
_reflns_number_gt                1910
_reflns_threshold_expression     'I > 2σ(I)'

_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0125P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4130
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0624
_refine_ls_wR_factor_gt          0.0531
_refine_ls_goodness_of_fit_ref   0.728
_refine_ls_restrained_S_all      0.728
_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
C1 C 0.1366(3) 0.1228(2) -0.08689(14) 0.0273(8) Uani 1 1 d . . . . .
H1 H 0.0631 0.0904 -0.1049 0.033 Uiso 1 1 calc R U . . .
C2 C 0.1534(4) 0.1928(2) -0.11079(16) 0.0328(8) Uani 1 1 d . . . . .
H2 H 0.0925 0.2085 -0.1447 0.039 Uiso 1 1 calc R U . . .
C3 C 0.2594(4) 0.2400(2) -0.08498(14) 0.0314(8) Uani 1 1 d . . . . .
H3 H 0.2727 0.2887 -0.1008 0.038 Uiso 1 1 calc R U . . .
C4 C 0.3466(4) 0.21556(19) -0.03572(14) 0.0275(7) Uani 1 1 d . . . . .
H4 H 0.4203 0.2473 -0.0171 0.033 Uiso 1 1 calc R U . . .
C5 C 0.3250(3) 0.14426(17) -0.01395(12) 0.0216(6) Uani 1 1 d . . . . .
C6 C 0.4157(3) 0.11401(19) 0.03951(14) 0.0239(7) Uani 1 1 d . . . . .
H6A H 0.5266 0.1141 0.0294 0.029 Uiso 1 1 calc R U . . .
H6B H 0.3998 0.1456 0.0762 0.029 Uiso 1 1 calc R U . . .
C7 C 0.4353(3) 0.0037(2) 0.09704(11) 0.0209(6) Uani 1 1 d . . . . .
H7 H 0.5139 0.0302 0.1179 0.025 Uiso 1 1 calc R U . . .
C8 C 0.4061(3) -0.06992(18) 0.11735(13) 0.0197(6) Uani 1 1 d . . . . .
C9 C 0.2975(3) -0.11629(17) 0.08859(12) 0.0203(6) Uani 1 1 d . . . . .
C10 C 0.2697(4) -0.19460(19) 0.10827(15) 0.0284(7) Uani 1 1 d . . . . .
H10A H 0.2190 -0.1949 0.1486 0.043 Uiso 1 1 calc R U . . .
H10B H 0.3681 -0.2208 0.1112 0.043 Uiso 1 1 calc R U . . .
H10C H 0.2039 -0.2194 0.0780 0.043 Uiso 1 1 calc R U . . .
C11 C 0.4960(4) -0.09685(17) 0.17028(12) 0.0257(6) Uani 1 1 d . . . . .
C12 C 0.6810(5) -0.0636(3) 0.24573(17) 0.0508(11) Uani 1 1 d . . . . .
H12A H 0.6161 -0.0720 0.2819 0.076 Uiso 1 1 calc R U . . .
H12B H 0.7540 -0.0235 0.2544 0.076 Uiso 1 1 calc R U . . .
H12C H 0.7375 -0.1091 0.2359 0.076 Uiso 1 1 calc R U . . .
C13 C 0.0846(3) -0.06997(18) -0.09894(13) 0.0216(6) Uani 1 1 d . . . . .
C14 C -0.0355(3) -0.0990(2) -0.14256(15) 0.0383(10) Uani 1 1 d . . . . .
H14A H 0.0107 -0.1072 -0.1832 0.057 Uiso 1 1 calc R U . . .
H14B H -0.1190 -0.0628 -0.1462 0.057 Uiso 1 1 calc R U . . .
H14C H -0.0765 -0.1459 -0.1268 0.057 Uiso 1 1 calc R U . . .
Cu1 Cu 0.19932(3) 0.00060(3) 0.00324(2) 0.01812(7) Uani 1 1 d . . . . .
N1 N 0.2205(3) 0.09846(16) -0.03882(11) 0.0208(6) Uani 1 1 d . . . . .
N2 N 0.3649(3) 0.03812(15) 0.05267(10) 0.0184(5) Uani 1 1 d . . . . .
O1 O 0.2150(2) -0.09542(13) 0.04313(9) 0.0229(5) Uani 1 1 d . . . . .
O2 O 0.4915(3) -0.15771(13) 0.19282(10) 0.0397(5) Uani 1 1 d . . . . .
O3 O 0.5858(3) -0.04304(15) 0.19399(11) 0.0396(6) Uani 1 1 d . . . . .
O4 O 0.03619(19) -0.03522(12) -0.05114(8) 0.0198(5) Uani 1 1 d . . . . .
O5 O 0.2229(2) -0.07875(13) -0.11047(9) 0.0257(5) Uani 1 1 d . . . . .
O21 O -0.0584(3) 0.27727(18) -0.22596(12) 0.0314(6) Uani 1 1 d . . . . .
O31 O 0.2904(3) -0.13869(16) -0.22632(11) 0.0338(6) Uani 1 1 d . . . . .
H21A H -0.041(4) 0.249(3) -0.249(2) 0.038(14) Uiso 1 1 d . . . . .
H21B H -0.121(5) 0.303(3) -0.2401(19) 0.044(14) Uiso 1 1 d . . . . .
H31A H 0.365(4) -0.156(2) -0.2259(16) 0.030(12) Uiso 1 1 d . . . . .
H31B H 0.274(4) -0.119(2) -0.1941(19) 0.043(12) Uiso 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
C1 N1 1.347(4) . ?
C1 C2 1.373(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.374(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(4) . ?
C4 H4 0.9500 . ?
C5 N1 1.342(4) . ?
C5 C6 1.505(4) . ?
C6 N2 1.466(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.300(4) . ?
C7 C8 1.421(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.408(4) . ?
C8 C11 1.472(4) . ?
C9 O1 1.277(3) . ?
C9 C10 1.495(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O2 1.202(3) . ?
C11 O3 1.348(4) . ?
C12 O3 1.444(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 O5 1.239(3) . ?
C13 O4 1.283(3) . ?
C13 C14 1.504(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
Cu1 N2 1.920(2) . ?
Cu1 O1 1.941(2) . ?
Cu1 O4 1.9560(18) . ?
Cu1 N1 1.995(3) . ?
Cu1 O4 2.3814(17) 5 ?
O4 Cu1 2.3813(17) 5 ?
O21 H21A 0.73(4) . ?
O21 H21B 0.77(4) . ?
O31 H31A 0.72(4) . ?
O31 H31B 0.80(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
N1 C1 C2 122.3(3) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 119.1(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 119.1(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 119.1(3) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 121.8(3) . . ?
N1 C5 C6 116.2(3) . . ?
C4 C5 C6 121.9(3) . . ?
N2 C6 C5 109.3(2) . . ?
N2 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
N2 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
N2 C7 C8 126.3(3) . . ?
N2 C7 H7 116.9 . . ?
C8 C7 H7 116.9 . . ?
C9 C8 C7 122.5(3) . . ?
C9 C8 C11 120.5(3) . . ?
C7 C8 C11 117.1(3) . . ?
O1 C9 C8 123.0(3) . . ?
O1 C9 C10 114.1(3) . . ?
C8 C9 C10 122.9(3) . . ?
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 . . ?
O2 C11 O3 121.4(3) . . ?
O2 C11 C8 127.0(3) . . ?
O3 C11 C8 111.6(3) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 C13 O4 123.0(3) . . ?
O5 C13 C14 120.2(3) . . ?
O4 C13 C14 116.8(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 Cu1 O1 90.70(10) . . ?
N2 Cu1 O4 176.81(10) . . ?
O1 Cu1 O4 91.47(9) . . ?
N2 Cu1 N1 82.80(11) . . ?
O1 Cu1 N1 170.63(8) . . ?
O4 Cu1 N1 94.77(10) . . ?
N2 Cu1 O4 108.03(8) . 5 ?
O1 Cu1 O4 95.72(8) . 5 ?
O4 Cu1 O4 74.07(8) . 5 ?
N1 Cu1 O4 92.73(9) . 5 ?
C5 N1 C1 118.6(3) . . ?
C5 N1 Cu1 115.02(19) . . ?
C1 N1 Cu1 126.3(2) . . ?
C7 N2 C6 116.7(3) . . ?
C7 N2 Cu1 126.8(2) . . ?
C6 N2 Cu1 116.49(18) . . ?
C9 O1 Cu1 130.3(2) . . ?
C11 O3 C12 116.4(3) . . ?
C13 O4 Cu1 114.27(17) . . ?
C13 O4 Cu1 139.79(17) . 5 ?
Cu1 O4 Cu1 105.93(8) . 5 ?
H21A O21 H21B 107(4) . . ?
H31A O31 H31B 110(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
N1 C1 C2 C3 0.0(5) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
C3 C4 C5 N1 -0.8(4) . . . . ?
C3 C4 C5 C6 -179.9(3) . . . . ?
N1 C5 C6 N2 -0.5(3) . . . . ?
C4 C5 C6 N2 178.7(3) . . . . ?
N2 C7 C8 C9 2.9(4) . . . . ?
N2 C7 C8 C11 -177.6(3) . . . . ?
C7 C8 C9 O1 -1.5(4) . . . . ?
C11 C8 C9 O1 179.0(3) . . . . ?
C7 C8 C9 C10 177.9(3) . . . . ?
C11 C8 C9 C10 -1.6(4) . . . . ?
C9 C8 C11 O2 2.1(5) . . . . ?
C7 C8 C11 O2 -177.4(3) . . . . ?
C9 C8 C11 O3 -175.8(3) . . . . ?
C7 C8 C11 O3 4.7(4) . . . . ?
C4 C5 N1 C1 1.0(4) . . . . ?
C6 C5 N1 C1 -179.9(3) . . . . ?
C4 C5 N1 Cu1 -176.2(2) . . . . ?
C6 C5 N1 Cu1 3.0(3) . . . . ?
C2 C1 N1 C5 -0.6(4) . . . . ?
C2 C1 N1 Cu1 176.2(2) . . . . ?
C8 C7 N2 C6 -179.5(3) . . . . ?
C8 C7 N2 Cu1 1.4(4) . . . . ?
C5 C6 N2 C7 178.5(2) . . . . ?
C5 C6 N2 Cu1 -2.4(3) . . . . ?
C8 C9 O1 Cu1 -4.0(4) . . . . ?
C10 C9 O1 Cu1 176.54(19) . . . . ?
O2 C11 O3 C12 2.9(5) . . . . ?
C8 C11 O3 C12 -179.2(3) . . . . ?
O5 C13 O4 Cu1 -1.5(4) . . . . ?
C14 C13 O4 Cu1 179.9(2) . . . . ?
O5 C13 O4 Cu1 -179.6(2) . . . 5 ?
C14 C13 O4 Cu1 1.9(5) . . . 5 ?

_refine_diff_density_max         0.359
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.071

####################################################################### 
# 
# 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_cl101
_database_code_depnum_ccdc_archive 'CCDC 1566639'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;


# start Validation Reply Form
_vrf_PLAT306_cl101               
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......        O71 Check 
RESPONSE: Refinement not stable after adding H-atoms.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;
_chemical_name_common            '[CuL30bN3]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H26 Cu2 N10 O4, 2(H2O)'
_chemical_formula_sum            'C24 H30 Cu2 N10 O6'
_chemical_formula_weight         681.66

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

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

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

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

_cell_length_a                   7.3993(4)
_cell_length_b                   9.3862(5)
_cell_length_c                   10.6959(5)
_cell_angle_alpha                105.369(4)
_cell_angle_beta                 99.166(4)
_cell_angle_gamma                97.860(4)
_cell_volume                     694.52(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    8571
_cell_measurement_theta_min      2.02
_cell_measurement_theta_max      26.62

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_F_000             350
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.098
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.059
_exptl_absorpt_coefficient_mu    1.590
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            7901
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.017
_diffrn_reflns_theta_max         28.428
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3289
_reflns_number_gt                2967
_reflns_threshold_expression     'I > 2σ(I)'


_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0395P)²+0.2007P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3289
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0686
_refine_ls_wR_factor_gt          0.0672
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
C1 C 0.5041(2) 0.75915(19) 0.23014(16) 0.0182(3) Uani 1 1 d . . . . .
H1 H 0.4548 0.7149 0.2908 0.022 Uiso 1 1 calc R U . . .
C2 C 0.4464(2) 0.6876(2) 0.09603(17) 0.0219(3) Uani 1 1 d . . . . .
H2 H 0.3612 0.5943 0.0648 0.026 Uiso 1 1 calc R U . . .
C3 C 0.5155(2) 0.7546(2) 0.00743(17) 0.0226(4) Uani 1 1 d . . . . .
H3 H 0.4758 0.7089 -0.0854 0.027 Uiso 1 1 calc R U . . .
C4 C 0.6427(2) 0.8884(2) 0.05608(16) 0.0206(3) Uani 1 1 d . . . . .
H4 H 0.6919 0.9356 -0.0028 0.025 Uiso 1 1 calc R U . . .
C5 C 0.6976(2) 0.95288(19) 0.19200(16) 0.0157(3) Uani 1 1 d . . . . .
C6 C 0.8417(2) 1.0951(2) 0.25134(16) 0.0195(3) Uani 1 1 d . . . . .
H6A H 0.9606 1.0792 0.2235 0.023 Uiso 1 1 calc R U . . .
H6B H 0.7995 1.1771 0.2193 0.023 Uiso 1 1 calc R U . . .
C7 C 0.9974(2) 1.25391(18) 0.46365(16) 0.0156(3) Uani 1 1 d . . . . .
H7 H 1.0687 1.3016 0.4145 0.019 Uiso 1 1 calc R U . . .
C8 C 1.0408(2) 1.31767(18) 0.60362(16) 0.0158(3) Uani 1 1 d . . . . .
C9 C 0.9593(2) 1.24606(19) 0.68839(16) 0.0161(3) Uani 1 1 d . . . . .
C10 C 1.0143(3) 1.3044(2) 0.83737(16) 0.0225(3) Uani 1 1 d . . . . .
H10A H 0.9500 1.3872 0.8695 0.034 Uiso 1 1 calc R U . . .
H10B H 1.1493 1.3407 0.8638 0.034 Uiso 1 1 calc R U . . .
H10C H 0.9793 1.2232 0.8756 0.034 Uiso 1 1 calc R U . . .
C11 C 1.1742(2) 1.46095(19) 0.65798(17) 0.0190(3) Uani 1 1 d . . . . .
C12 C 1.3141(2) 1.5015(2) 0.57845(19) 0.0235(4) Uani 1 1 d . . . . .
H12A H 1.2520 1.5345 0.5060 0.035 Uiso 1 1 calc R U . . .
H12B H 1.3673 1.4132 0.5417 0.035 Uiso 1 1 calc R U . . .
H12C H 1.4139 1.5830 0.6360 0.035 Uiso 1 1 calc R U . . .
N1 N 0.62815(19) 0.89002(16) 0.27779(13) 0.0150(3) Uani 1 1 d . . . . .
N2 N 0.87047(19) 1.13719(16) 0.39591(13) 0.0154(3) Uani 1 1 d . . . . .
N3 N 0.56549(19) 0.86706(16) 0.53549(13) 0.0165(3) Uani 1 1 d . . . . .
N4 N 0.62008(19) 0.85705(16) 0.64414(14) 0.0164(3) Uani 1 1 d . . . . .
N5 N 0.6673(2) 0.8432(2) 0.74759(15) 0.0275(3) Uani 1 1 d . . . . .
O1 O 0.84112(17) 1.12360(14) 0.64585(11) 0.0185(2) Uani 1 1 d . . . . .
O2 O 1.1759(2) 1.54975(15) 0.76575(13) 0.0270(3) Uani 1 1 d . . . . .
O71 O 0.7958(3) 1.5743(3) 0.7985(3) 0.0748(7) Uani 1 1 d . . . . .
Cu1 Cu 0.71578(3) 1.01076(2) 0.46768(2) 0.01348(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
C1 N1 1.350(2) . ?
C1 C2 1.381(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.392(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(2) . ?
C4 H4 0.9500 . ?
C5 N1 1.345(2) . ?
C5 C6 1.506(2) . ?
C6 N2 1.463(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.299(2) . ?
C7 C8 1.422(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.423(2) . ?
C8 C11 1.470(2) . ?
C9 O1 1.270(2) . ?
C9 C10 1.508(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O2 1.227(2) . ?
C11 C12 1.512(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N1 Cu1 1.9973(14) . ?
N2 Cu1 1.9233(13) . ?
N3 N4 1.200(2) . ?
N3 Cu1 1.9867(14) . ?
N4 N5 1.153(2) . ?
O1 Cu1 1.9266(12) . ?

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
N1 C1 C2 122.06(15) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C1 C2 C3 118.78(16) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 119.18(16) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 119.13(16) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 121.82(15) . . ?
N1 C5 C6 116.47(14) . . ?
C4 C5 C6 121.69(15) . . ?
N2 C6 C5 109.67(13) . . ?
N2 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 126.77(15) . . ?
N2 C7 H7 116.6 . . ?
C8 C7 H7 116.6 . . ?
C7 C8 C9 121.63(14) . . ?
C7 C8 C11 117.38(14) . . ?
C9 C8 C11 120.99(15) . . ?
O1 C9 C8 123.21(15) . . ?
O1 C9 C10 113.96(14) . . ?
C8 C9 C10 122.74(15) . . ?
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 . . ?
O2 C11 C8 122.42(16) . . ?
O2 C11 C12 118.50(16) . . ?
C8 C11 C12 119.08(15) . . ?
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 . . ?
C5 N1 C1 119.00(14) . . ?
C5 N1 Cu1 114.35(11) . . ?
C1 N1 Cu1 126.59(11) . . ?
C7 N2 C6 117.90(14) . . ?
C7 N2 Cu1 126.12(11) . . ?
C6 N2 Cu1 115.98(11) . . ?
N4 N3 Cu1 119.47(11) . . ?
N5 N4 N3 177.56(17) . . ?
C9 O1 Cu1 130.27(11) . . ?
N2 Cu1 O1 91.22(5) . . ?
N2 Cu1 N3 175.52(6) . . ?
O1 Cu1 N3 90.56(5) . . ?
N2 Cu1 N1 83.21(6) . . ?
O1 Cu1 N1 170.48(5) . . ?
N3 Cu1 N1 94.46(6) . . ?

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
N1 C1 C2 C3 -1.5(3) . . . . ?
C1 C2 C3 C4 1.5(3) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 N1 -1.1(3) . . . . ?
C3 C4 C5 C6 177.35(16) . . . . ?
N1 C5 C6 N2 -1.9(2) . . . . ?
C4 C5 C6 N2 179.55(16) . . . . ?
N2 C7 C8 C9 7.6(3) . . . . ?
N2 C7 C8 C11 -172.63(16) . . . . ?
C7 C8 C9 O1 -1.4(3) . . . . ?
C11 C8 C9 O1 178.80(15) . . . . ?
C7 C8 C9 C10 174.87(16) . . . . ?
C11 C8 C9 C10 -4.9(3) . . . . ?
C7 C8 C11 O2 154.96(17) . . . . ?
C9 C8 C11 O2 -25.2(3) . . . . ?
C7 C8 C11 C12 -24.8(2) . . . . ?
C9 C8 C11 C12 155.06(16) . . . . ?
C4 C5 N1 C1 1.2(2) . . . . ?
C6 C5 N1 C1 -177.35(15) . . . . ?
C4 C5 N1 Cu1 -176.13(13) . . . . ?
C6 C5 N1 Cu1 5.32(19) . . . . ?
C2 C1 N1 C5 0.1(3) . . . . ?
C2 C1 N1 Cu1 177.10(13) . . . . ?
C8 C7 N2 C6 176.68(16) . . . . ?
C8 C7 N2 Cu1 -4.1(3) . . . . ?
C5 C6 N2 C7 176.76(15) . . . . ?
C5 C6 N2 Cu1 -2.57(18) . . . . ?
C8 C9 O1 Cu1 -7.8(2) . . . . ?
C10 C9 O1 Cu1 175.65(12) . . . . ?

_refine_diff_density_max         0.418
_refine_diff_density_min         -0.692
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_cl068
_database_code_depnum_ccdc_archive 'CCDC 1566613'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;
_chemical_name_common            HL30f
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 N2 O3'
_chemical_formula_sum            'C18 H18 N2 O3'
_chemical_formula_weight         310.34

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'

_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                   5.5863(5)
_cell_length_b                   11.6567(11)
_cell_length_c                   13.2094(12)
_cell_angle_alpha                71.808(7)
_cell_angle_beta                 79.534(7)
_cell_angle_gamma                77.545(7)
_cell_volume                     791.86(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    4536
_cell_measurement_theta_min      1.64
_cell_measurement_theta_max      28.08

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.145
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            6984
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.866
_diffrn_reflns_theta_max         28.064
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             3448
_reflns_number_gt                2285
_reflns_threshold_expression     'I > 2σ(I)'


_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0779P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3448
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1397
_refine_ls_wR_factor_gt          0.1255
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_restrained_S_all      0.965
_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
C1 C 0.1520(4) 0.92546(19) 1.12045(18) 0.0335(5) Uani 1 1 d . . . . .
H1 H -0.0082 0.9702 1.1072 0.040 Uiso 1 1 calc R U . . .
C2 C 0.2267(4) 0.9090(2) 1.21902(19) 0.0384(5) Uani 1 1 d . . . . .
H2B H 0.1194 0.9405 1.2723 0.046 Uiso 1 1 calc R U . . .
C3 C 0.4598(5) 0.8460(2) 1.23799(19) 0.0403(5) Uani 1 1 d . . . . .
H3 H 0.5181 0.8345 1.3043 0.048 Uiso 1 1 calc R U . . .
C4 C 0.6086(4) 0.79941(19) 1.15858(18) 0.0324(5) Uani 1 1 d . . . . .
H4 H 0.7699 0.7549 1.1698 0.039 Uiso 1 1 calc R U . . .
C5 C 0.5173(3) 0.81901(17) 1.06281(15) 0.0247(4) Uani 1 1 d . . . . .
C6 C 0.6730(4) 0.77043(19) 0.97337(16) 0.0291(4) Uani 1 1 d . . . . .
H6A H 0.7371 0.8389 0.9166 0.035 Uiso 1 1 calc R U . . .
H6B H 0.8163 0.7102 1.0022 0.035 Uiso 1 1 calc R U . . .
C7 C 0.4183(3) 0.77152(17) 0.84245(15) 0.0257(4) Uani 1 1 d . . . . .
H7 H 0.4341 0.8552 0.8113 0.031 Uiso 1 1 calc R U . . .
C8 C 0.2747(3) 0.72552(17) 0.79353(15) 0.0247(4) Uani 1 1 d . . . . .
C9 C 0.2435(3) 0.59891(17) 0.83424(14) 0.0229(4) Uani 1 1 d . . . . .
C10 C 0.1391(3) 0.53772(16) 0.77168(14) 0.0225(4) Uani 1 1 d . . . . .
C11 C -0.0659(3) 0.48277(17) 0.81835(15) 0.0257(4) Uani 1 1 d . . . . .
H11 H -0.1421 0.4868 0.8879 0.031 Uiso 1 1 calc R U . . .
C12 C -0.1602(4) 0.42186(18) 0.76361(17) 0.0287(4) Uani 1 1 d . . . . .
H12 H -0.3050 0.3872 0.7943 0.034 Uiso 1 1 calc R U . . .
C13 C -0.0429(4) 0.41154(19) 0.66378(17) 0.0309(4) Uani 1 1 d . . . . .
H13 H -0.1062 0.3688 0.6268 0.037 Uiso 1 1 calc R U . . .
C14 C 0.1647(4) 0.46329(19) 0.61860(16) 0.0302(4) Uani 1 1 d . . . . .
H14 H 0.2464 0.4547 0.5510 0.036 Uiso 1 1 calc R U . . .
C15 C 0.2553(4) 0.52771(18) 0.67093(15) 0.0266(4) Uani 1 1 d . . . . .
H15 H 0.3962 0.5651 0.6385 0.032 Uiso 1 1 calc R U . . .
C16 C 0.1597(4) 0.81651(17) 0.70321(15) 0.0263(4) Uani 1 1 d . . . . .
C17 C -0.1341(5) 0.8603(2) 0.5802(2) 0.0435(6) Uani 1 1 d . . . . .
H17A H -0.0063 0.8982 0.5253 0.052 Uiso 1 1 calc R U . . .
H17B H -0.2599 0.9264 0.5998 0.052 Uiso 1 1 calc R U . . .
C18 C -0.2508(5) 0.7852(2) 0.5372(2) 0.0466(6) Uani 1 1 d . . . . .
H18A H -0.1269 0.7171 0.5221 0.070 Uiso 1 1 calc R U . . .
H18B H -0.3178 0.8362 0.4708 0.070 Uiso 1 1 calc R U . . .
H18C H -0.3848 0.7527 0.5903 0.070 Uiso 1 1 calc R U . . .
N1 N 0.2929(3) 0.88191(15) 1.04241(14) 0.0291(4) Uani 1 1 d . . . . .
N2 N 0.5341(3) 0.71255(15) 0.92666(13) 0.0264(4) Uani 1 1 d . . . . .
H2A H 0.5272 0.6342 0.9561 0.032 Uiso 1 1 calc R U . . .
O1 O 0.3130(3) 0.53301(12) 0.92155(11) 0.0284(3) Uani 1 1 d . . . . .
O2 O 0.2159(3) 0.91713(13) 0.65946(12) 0.0339(4) Uani 1 1 d . . . . .
O3 O -0.0230(3) 0.78003(13) 0.67455(13) 0.0372(4) 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
C1 N1 1.341(3) . ?
C1 C2 1.383(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.374(3) . ?
C2 H2B 0.9500 . ?
C3 C4 1.390(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.336(2) . ?
C5 C6 1.518(3) . ?
C6 N2 1.448(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.312(3) . ?
C7 C8 1.392(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.442(3) . ?
C8 C16 1.468(3) . ?
C9 O1 1.246(2) . ?
C9 C10 1.502(3) . ?
C10 C11 1.384(3) . ?
C10 C15 1.399(2) . ?
C11 C12 1.387(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.375(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 O2 1.216(2) . ?
C16 O3 1.339(2) . ?
C17 O3 1.455(3) . ?
C17 C18 1.485(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N2 H2A 0.8800 . ?

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
N1 C1 C2 123.8(2) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 H2B 120.8 . . ?
C1 C2 H2B 120.8 . . ?
C2 C3 C4 118.9(2) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 123.08(19) . . ?
N1 C5 C6 116.11(17) . . ?
C4 C5 C6 120.81(18) . . ?
N2 C6 C5 112.23(16) . . ?
N2 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N2 C7 C8 127.46(18) . . ?
N2 C7 H7 116.3 . . ?
C8 C7 H7 116.3 . . ?
C7 C8 C9 120.17(17) . . ?
C7 C8 C16 114.37(17) . . ?
C9 C8 C16 125.44(17) . . ?
O1 C9 C8 121.29(17) . . ?
O1 C9 C10 116.47(16) . . ?
C8 C9 C10 122.17(16) . . ?
C11 C10 C15 119.62(17) . . ?
C11 C10 C9 118.99(16) . . ?
C15 C10 C9 121.22(16) . . ?
C10 C11 C12 119.99(18) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 120.07(18) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 119.96(19) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.39(18) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 119.90(18) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
O2 C16 O3 122.05(18) . . ?
O2 C16 C8 124.53(19) . . ?
O3 C16 C8 113.38(16) . . ?
O3 C17 C18 107.96(19) . . ?
O3 C17 H17A 110.1 . . ?
C18 C17 H17A 110.1 . . ?
O3 C17 H17B 110.1 . . ?
C18 C17 H17B 110.1 . . ?
H17A C17 H17B 108.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C5 N1 C1 117.10(18) . . ?
C7 N2 C6 123.01(17) . . ?
C7 N2 H2A 118.5 . . ?
C6 N2 H2A 118.5 . . ?
C16 O3 C17 117.10(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 1.0(4) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 N1 0.7(3) . . . . ?
C3 C4 C5 C6 179.76(19) . . . . ?
N1 C5 C6 N2 -45.9(2) . . . . ?
C4 C5 C6 N2 135.01(19) . . . . ?
N2 C7 C8 C9 -1.0(3) . . . . ?
N2 C7 C8 C16 177.30(18) . . . . ?
C7 C8 C9 O1 10.3(3) . . . . ?
C16 C8 C9 O1 -167.84(17) . . . . ?
C7 C8 C9 C10 -166.39(16) . . . . ?
C16 C8 C9 C10 15.5(3) . . . . ?
O1 C9 C10 C11 59.1(2) . . . . ?
C8 C9 C10 C11 -124.03(19) . . . . ?
O1 C9 C10 C15 -116.2(2) . . . . ?
C8 C9 C10 C15 60.6(2) . . . . ?
C15 C10 C11 C12 -2.2(3) . . . . ?
C9 C10 C11 C12 -177.66(17) . . . . ?
C10 C11 C12 C13 2.7(3) . . . . ?
C11 C12 C13 C14 -0.9(3) . . . . ?
C12 C13 C14 C15 -1.2(3) . . . . ?
C13 C14 C15 C10 1.6(3) . . . . ?
C11 C10 C15 C14 0.1(3) . . . . ?
C9 C10 C15 C14 175.41(18) . . . . ?
C7 C8 C16 O2 13.5(3) . . . . ?
C9 C8 C16 O2 -168.32(18) . . . . ?
C7 C8 C16 O3 -164.39(16) . . . . ?
C9 C8 C16 O3 13.8(3) . . . . ?
C4 C5 N1 C1 -1.0(3) . . . . ?
C6 C5 N1 C1 179.86(18) . . . . ?
C2 C1 N1 C5 0.2(3) . . . . ?
C8 C7 N2 C6 -178.00(18) . . . . ?
C5 C6 N2 C7 92.4(2) . . . . ?
O2 C16 O3 C17 6.9(3) . . . . ?
C8 C16 O3 C17 -175.19(19) . . . . ?
C18 C17 O3 C16 157.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O1 0.88 2.04 2.673(2) 127.6 .

_refine_diff_density_max         0.397
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_cl126
_database_code_depnum_ccdc_archive 'CCDC 1566641'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;


# start Validation Reply Form
_vrf_DIFMN02_cl126               
;
PROBLEM: The minimum difference density is < -0.1*ZMAX*1.00
RESPONSE: Crystal of very low quality, partly dried. 
Will only be discussed as motif.
;
_vrf_RFACR01_cl126               
;
PROBLEM: The value of the weighted R factor is > 0.35
RESPONSE: Crystal of very low quality, partly dried. 
Will only be discussed as motif.
;
_vrf_RINTA01_cl126               
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: Crystal of very low quality, partly dried. 
Will only be discussed as motif.
;
_vrf_PLAT020_cl126               
;
PROBLEM: The value of Rint is greater than 0.12 .........      0.216 Report
RESPONSE: Crystal of very low quality, partly dried. 
Will only be discussed as motif.
;
_vrf_PLAT084_cl126               
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.37 Report
RESPONSE: Crystal of very low quality, partly dried. 
Will only be discussed as motif.
;
_vrf_PLAT098_cl126               
;
PROBLEM: Large Reported Min.  (Negative) Residual Density      -3.48 eA-3  
RESPONSE: Crystal of very low quality, partly dried. 
Will only be discussed as motif.
;
_vrf_PLAT306_cl126               
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......        O71 Check 
RESPONSE: Addition of H-atoms leads to unstable refinement. 
;
_vrf_PLAT430_cl126               
;
PROBLEM: Short Inter D...A Contact  O53    ..  O71     ..       2.79 Ang.  
RESPONSE: missing H-atoms on O71
;
_vrf_PLAT972_cl126               
;
PROBLEM: Check Calcd Residual Density  0.85A From     Cu1      -3.19 eA-3  
RESPONSE: Crystal of very low quality, partly dried. 
Will only be discussed as motif.
;
_vrf_PLAT973_cl126               
;
PROBLEM: Check Calcd Positive Residual Density on     Cu1       1.96 eA-3  
RESPONSE: Crystal of very low quality, partly dried. 
Will only be discussed as motif.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;
_chemical_name_common            '[CuL30c]2SO4'
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H34 Cu2 N4 O12 S, C H4 O, H2O'
_chemical_formula_sum            'C29 H40 Cu2 N4 O14 S'
_chemical_formula_weight         827.81

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   6.7842(6)
_cell_length_b                   15.8946(15)
_cell_length_c                   15.9754(18)
_cell_angle_alpha                93.458(9)
_cell_angle_beta                 96.606(8)
_cell_angle_gamma                97.754(8)
_cell_volume                     1690.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    11131
_cell_measurement_theta_min      1.76
_cell_measurement_theta_max      28.26

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_F_000             852
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.086
_exptl_absorpt_coefficient_mu    1.394
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            19376
_diffrn_reflns_av_unetI/netI     0.1729
_diffrn_reflns_av_R_equivalents  0.2163
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.755
_diffrn_reflns_theta_max         28.528
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             7952
_reflns_number_gt                4466
_reflns_threshold_expression     'I > 2σ(I)'


_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       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7952
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1789
_refine_ls_R_factor_gt           0.1353
_refine_ls_wR_factor_ref         0.3733
_refine_ls_wR_factor_gt          0.3285
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_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
C1 C 0.3180(11) 0.0608(5) -0.0765(6) 0.0406(18) Uani 1 1 d . . . . .
H1 H 0.3485 0.1211 -0.0702 0.049 Uiso 1 1 calc R U . . .
C2 C 0.3288(12) 0.0183(6) -0.1531(6) 0.0432(18) Uani 1 1 d . . . . .
H2 H 0.3693 0.0489 -0.1990 0.052 Uiso 1 1 calc R U . . .
C3 C 0.2804(13) -0.0686(6) -0.1624(6) 0.046(2) Uani 1 1 d . . . . .
H3 H 0.2862 -0.0983 -0.2152 0.056 Uiso 1 1 calc R U . . .
C4 C 0.2239(12) -0.1128(5) -0.0965(6) 0.045(2) Uani 1 1 d . . . . .
H4 H 0.1895 -0.1730 -0.1031 0.054 Uiso 1 1 calc R U . . .
C5 C 0.2178(12) -0.0676(5) -0.0189(6) 0.0410(18) Uani 1 1 d . . . . .
C6 C 0.1617(12) -0.1100(5) 0.0582(6) 0.0408(18) Uani 1 1 d . . . . .
H6A H 0.0237 -0.1412 0.0464 0.049 Uiso 1 1 calc R U . . .
H6B H 0.2539 -0.1516 0.0729 0.049 Uiso 1 1 calc R U . . .
C7 C 0.1503(11) -0.0748(5) 0.2031(6) 0.0381(18) Uani 1 1 d . . . . .
H7 H 0.1226 -0.1348 0.2047 0.046 Uiso 1 1 calc R U . . .
C8 C 0.1627(11) -0.0250(5) 0.2816(6) 0.0404(18) Uani 1 1 d . . . . .
C9 C 0.2068(11) 0.0661(5) 0.2830(6) 0.0402(18) Uani 1 1 d . . . . .
C10 C 0.2506(15) 0.2021(5) 0.3592(7) 0.049(2) Uani 1 1 d . . . . .
H10A H 0.1943 0.2280 0.4074 0.059 Uiso 1 1 calc R U . . .
H10B H 0.1883 0.2227 0.3066 0.059 Uiso 1 1 calc R U . . .
C11 C 0.4714(15) 0.2286(6) 0.3687(7) 0.055(2) Uani 1 1 d . . . . .
H11A H 0.5270 0.2268 0.4278 0.083 Uiso 1 1 calc R U . . .
H11B H 0.5004 0.2867 0.3515 0.083 Uiso 1 1 calc R U . . .
H11C H 0.5324 0.1898 0.3329 0.083 Uiso 1 1 calc R U . . .
C12 C 0.1259(12) -0.0757(5) 0.3537(6) 0.0431(19) Uani 1 1 d . . . . .
C13 C 0.1588(13) -0.0845(6) 0.5015(6) 0.049(2) Uani 1 1 d . . . . .
H13A H 0.2048 -0.1407 0.4937 0.059 Uiso 1 1 calc R U . . .
H13B H 0.0138 -0.0939 0.5072 0.059 Uiso 1 1 calc R U . . .
C14 C 0.2751(15) -0.0343(7) 0.5795(7) 0.056(2) Uani 1 1 d . . . . .
H14A H 0.4188 -0.0277 0.5742 0.084 Uiso 1 1 calc R U . . .
H14B H 0.2496 -0.0647 0.6296 0.084 Uiso 1 1 calc R U . . .
H14C H 0.2322 0.0220 0.5851 0.084 Uiso 1 1 calc R U . . .
C21 C 0.1345(11) 0.3393(5) -0.1418(6) 0.0414(18) Uani 1 1 d . . . . .
H21 H 0.1543 0.2903 -0.1125 0.050 Uiso 1 1 calc R U . . .
C22 C 0.0659(12) 0.3307(6) -0.2265(7) 0.047(2) Uani 1 1 d . . . . .
H22 H 0.0392 0.2759 -0.2561 0.056 Uiso 1 1 calc R U . . .
C23 C 0.0355(13) 0.4034(6) -0.2692(6) 0.0465(19) Uani 1 1 d . . . . .
H23 H -0.0129 0.3983 -0.3277 0.056 Uiso 1 1 calc R U . . .
C24 C 0.0774(12) 0.4835(5) -0.2242(6) 0.0440(19) Uani 1 1 d . . . . .
H24 H 0.0587 0.5336 -0.2517 0.053 Uiso 1 1 calc R U . . .
C25 C 0.1460(11) 0.4881(5) -0.1396(6) 0.0378(17) Uani 1 1 d . . . . .
C26 C 0.2007(13) 0.5714(5) -0.0876(6) 0.045(2) Uani 1 1 d . . . . .
H26A H 0.3102 0.6069 -0.1106 0.054 Uiso 1 1 calc R U . . .
H26B H 0.0834 0.6025 -0.0899 0.054 Uiso 1 1 calc R U . . .
C27 C 0.3164(12) 0.6223(5) 0.0559(6) 0.0416(19) Uani 1 1 d . . . . .
H27 H 0.3115 0.6765 0.0343 0.050 Uiso 1 1 calc R U . . .
C28 C 0.3756(12) 0.6219(5) 0.1414(6) 0.0421(18) Uani 1 1 d . . . . .
C29 C 0.3856(11) 0.5417(5) 0.1796(6) 0.0387(18) Uani 1 1 d . . . . .
C30 C 0.4350(14) 0.4626(6) 0.3001(7) 0.050(2) Uani 1 1 d . . . . .
H30A H 0.5425 0.4332 0.2801 0.060 Uiso 1 1 calc R U . . .
H30B H 0.3050 0.4254 0.2848 0.060 Uiso 1 1 calc R U . . .
C31 C 0.4753(18) 0.4844(7) 0.3953(7) 0.064(3) Uani 1 1 d . . . . .
H31A H 0.5990 0.5249 0.4087 0.096 Uiso 1 1 calc R U . . .
H31B H 0.4899 0.4324 0.4239 0.096 Uiso 1 1 calc R U . . .
H31C H 0.3630 0.5099 0.4144 0.096 Uiso 1 1 calc R U . . .
C32 C 0.4325(12) 0.7064(6) 0.1880(7) 0.046(2) Uani 1 1 d . . . . .
C33 C 0.5354(14) 0.7875(5) 0.3168(6) 0.046(2) Uani 1 1 d . . . . .
H33A H 0.4323 0.8256 0.3073 0.056 Uiso 1 1 calc R U . . .
H33B H 0.6604 0.8144 0.2972 0.056 Uiso 1 1 calc R U . . .
C34 C 0.571(2) 0.7732(7) 0.4069(8) 0.072(3) Uani 1 1 d . . . . .
H34A H 0.4524 0.7394 0.4236 0.108 Uiso 1 1 calc R U . . .
H34B H 0.5987 0.8282 0.4403 0.108 Uiso 1 1 calc R U . . .
H34C H 0.6868 0.7425 0.4168 0.108 Uiso 1 1 calc R U . . .
C61 C 0.042(2) 0.6239(8) 0.5259(9) 0.074(3) Uani 1 1 d . . . . .
H61A H -0.0858 0.6453 0.5112 0.111 Uiso 1 1 calc R U . . .
H61B H 0.0526 0.5765 0.4853 0.111 Uiso 1 1 calc R U . . .
H61C H 0.1530 0.6696 0.5241 0.111 Uiso 1 1 calc R U . . .
N1 N 0.2643(10) 0.0179(4) -0.0098(5) 0.0406(15) Uani 1 1 d . . . . .
N2 N 0.1733(10) -0.0462(4) 0.1291(5) 0.0432(17) Uani 1 1 d . . . . .
N21 N 0.1743(10) 0.4178(4) -0.0997(5) 0.0388(15) Uani 1 1 d . . . . .
N22 N 0.2662(10) 0.5558(4) 0.0012(5) 0.0402(15) Uani 1 1 d . . . . .
O1 O 0.2412(9) 0.1071(4) 0.2209(4) 0.0454(14) Uani 1 1 d . . . . .
O2 O 0.2034(9) 0.1089(4) 0.3562(4) 0.0463(14) Uani 1 1 d . . . . .
O3 O 0.0455(10) -0.1490(4) 0.3460(4) 0.0504(15) Uani 1 1 d . . . . .
O4 O 0.1947(9) -0.0351(4) 0.4301(4) 0.0443(13) Uani 1 1 d . . . . .
O21 O 0.3562(8) 0.4702(3) 0.1385(4) 0.0428(13) Uani 1 1 d . . . . .
O22 O 0.4312(9) 0.5444(4) 0.2631(4) 0.0434(13) Uani 1 1 d . . . . .
O23 O 0.4458(10) 0.7734(4) 0.1514(4) 0.0500(15) Uani 1 1 d . . . . .
O24 O 0.4675(9) 0.7056(4) 0.2711(4) 0.0444(14) Uani 1 1 d . . . . .
O52 O 0.2731(10) 0.1796(4) 0.0645(4) 0.0478(15) Uani 1 1 d . . . . .
O53 O 0.4716(9) 0.2842(4) 0.1661(5) 0.0510(15) Uani 1 1 d . . . . .
O54 O 0.1176(9) 0.2828(4) 0.1417(5) 0.0506(16) Uani 1 1 d . . . . .
O55 O 0.3185(9) 0.3236(3) 0.0318(4) 0.0451(14) Uani 1 1 d . . . . .
O62 O 0.0486(16) 0.5962(6) 0.6056(6) 0.089(3) Uani 1 1 d . . . . .
H62 H 0.0833 0.6380 0.6414 0.134 Uiso 1 1 calc R U . . .
O71 O 0.8478(10) 0.2857(5) 0.2582(5) 0.065(2) Uani 1 1 d . . . . .
Cu1 Cu 0.24097(14) 0.06891(6) 0.10507(7) 0.0393(3) Uani 1 1 d . . . . .
Cu2 Cu 0.28015(14) 0.43960(6) 0.02144(7) 0.0388(3) Uani 1 1 d . . . . .
S51 S 0.2957(3) 0.26889(11) 0.10567(14) 0.0382(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
C1 N1 1.357(11) . ?
C1 C2 1.376(13) . ?
C1 H1 0.9500 . ?
C2 C3 1.371(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.363(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.404(13) . ?
C4 H4 0.9500 . ?
C5 N1 1.349(10) . ?
C5 C6 1.501(12) . ?
C6 N2 1.462(11) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.311(12) . ?
C7 C8 1.430(12) . ?
C7 H7 0.9500 . ?
C8 C9 1.437(11) . ?
C8 C12 1.469(13) . ?
C9 O1 1.246(11) . ?
C9 O2 1.321(11) . ?
C10 O2 1.470(10) . ?
C10 C11 1.489(13) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O3 1.211(10) . ?
C12 O4 1.348(11) . ?
C13 O4 1.448(11) . ?
C13 C14 1.515(14) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C21 N21 1.359(10) . ?
C21 C22 1.373(14) . ?
C21 H21 0.9500 . ?
C22 C23 1.402(13) . ?
C22 H22 0.9500 . ?
C23 C24 1.401(13) . ?
C23 H23 0.9500 . ?
C24 C25 1.372(13) . ?
C24 H24 0.9500 . ?
C25 N21 1.344(10) . ?
C25 C26 1.499(12) . ?
C26 N22 1.483(12) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 N22 1.312(11) . ?
C27 C28 1.380(13) . ?
C27 H27 0.9500 . ?
C28 C29 1.453(11) . ?
C28 C32 1.476(12) . ?
C29 O21 1.258(10) . ?
C29 O22 1.330(11) . ?
C30 O22 1.462(10) . ?
C30 C31 1.524(15) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 O23 1.244(11) . ?
C32 O24 1.323(12) . ?
C33 O24 1.445(10) . ?
C33 C34 1.468(15) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C61 O62 1.370(16) . ?
C61 H61A 0.9800 . ?
C61 H61B 0.9800 . ?
C61 H61C 0.9800 . ?
N1 Cu1 1.993(8) . ?
N2 Cu1 1.898(7) . ?
N21 Cu2 1.978(8) . ?
N22 Cu2 1.907(6) . ?
O1 Cu1 1.913(7) . ?
O21 Cu2 1.898(7) . ?
O52 S51 1.509(6) . ?
O52 Cu1 1.905(6) . ?
O53 S51 1.430(7) . ?
O54 S51 1.434(6) . ?
O55 S51 1.517(6) . ?
O55 Cu2 1.911(5) . ?
O62 H62 0.8400 . ?

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
N1 C1 C2 121.1(7) . . ?
N1 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C3 C2 C1 119.2(8) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C4 C3 C2 120.7(9) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 118.6(8) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 120.7(8) . . ?
N1 C5 C6 116.2(8) . . ?
C4 C5 C6 123.1(7) . . ?
N2 C6 C5 109.9(7) . . ?
N2 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 126.8(7) . . ?
N2 C7 H7 116.6 . . ?
C8 C7 H7 116.6 . . ?
C7 C8 C9 119.0(8) . . ?
C7 C8 C12 114.0(7) . . ?
C9 C8 C12 127.1(8) . . ?
O1 C9 O2 118.2(7) . . ?
O1 C9 C8 125.6(8) . . ?
O2 C9 C8 116.2(8) . . ?
O2 C10 C11 110.4(7) . . ?
O2 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
O2 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 O4 121.8(9) . . ?
O3 C12 C8 123.3(9) . . ?
O4 C12 C8 114.8(7) . . ?
O4 C13 C14 107.2(8) . . ?
O4 C13 H13A 110.3 . . ?
C14 C13 H13A 110.3 . . ?
O4 C13 H13B 110.3 . . ?
C14 C13 H13B 110.3 . . ?
H13A C13 H13B 108.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N21 C21 C22 120.2(8) . . ?
N21 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C23 119.6(8) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C24 C23 C22 119.0(9) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C25 C24 C23 118.8(8) . . ?
C25 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?
N21 C25 C24 121.4(8) . . ?
N21 C25 C26 116.4(8) . . ?
C24 C25 C26 122.1(8) . . ?
N22 C26 C25 109.6(7) . . ?
N22 C26 H26A 109.8 . . ?
C25 C26 H26A 109.8 . . ?
N22 C26 H26B 109.8 . . ?
C25 C26 H26B 109.8 . . ?
H26A C26 H26B 108.2 . . ?
N22 C27 C28 126.8(8) . . ?
N22 C27 H27 116.6 . . ?
C28 C27 H27 116.6 . . ?
C27 C28 C29 120.1(8) . . ?
C27 C28 C32 115.8(8) . . ?
C29 C28 C32 124.1(9) . . ?
O21 C29 O22 118.2(7) . . ?
O21 C29 C28 124.0(8) . . ?
O22 C29 C28 117.8(7) . . ?
O22 C30 C31 105.2(8) . . ?
O22 C30 H30A 110.7 . . ?
C31 C30 H30A 110.7 . . ?
O22 C30 H30B 110.7 . . ?
C31 C30 H30B 110.7 . . ?
H30A C30 H30B 108.8 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O23 C32 O24 122.6(8) . . ?
O23 C32 C28 122.1(9) . . ?
O24 C32 C28 115.3(8) . . ?
O24 C33 C34 107.5(8) . . ?
O24 C33 H33A 110.2 . . ?
C34 C33 H33A 110.2 . . ?
O24 C33 H33B 110.2 . . ?
C34 C33 H33B 110.2 . . ?
H33A C33 H33B 108.5 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O62 C61 H61A 109.5 . . ?
O62 C61 H61B 109.5 . . ?
H61A C61 H61B 109.5 . . ?
O62 C61 H61C 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
C5 N1 C1 119.6(8) . . ?
C5 N1 Cu1 113.9(6) . . ?
C1 N1 Cu1 126.4(6) . . ?
C7 N2 C6 116.6(7) . . ?
C7 N2 Cu1 127.1(6) . . ?
C6 N2 Cu1 116.0(6) . . ?
C25 N21 C21 121.0(8) . . ?
C25 N21 Cu2 114.6(6) . . ?
C21 N21 Cu2 124.4(6) . . ?
C27 N22 C26 117.5(7) . . ?
C27 N22 Cu2 127.2(7) . . ?
C26 N22 Cu2 115.2(5) . . ?
C9 O1 Cu1 130.3(6) . . ?
C9 O2 C10 117.1(7) . . ?
C12 O4 C13 115.2(7) . . ?
C29 O21 Cu2 130.9(6) . . ?
C29 O22 C30 116.6(7) . . ?
C32 O24 C33 115.6(7) . . ?
S51 O52 Cu1 134.3(5) . . ?
S51 O55 Cu2 129.9(4) . . ?
C61 O62 H62 109.5 . . ?
N2 Cu1 O52 169.9(3) . . ?
N2 Cu1 O1 91.2(3) . . ?
O52 Cu1 O1 95.8(3) . . ?
N2 Cu1 N1 83.8(3) . . ?
O52 Cu1 N1 89.9(3) . . ?
O1 Cu1 N1 172.3(3) . . ?
O21 Cu2 N22 90.6(3) . . ?
O21 Cu2 O55 93.2(3) . . ?
N22 Cu2 O55 172.8(3) . . ?
O21 Cu2 N21 172.5(2) . . ?
N22 Cu2 N21 84.1(3) . . ?
O55 Cu2 N21 92.7(3) . . ?
O53 S51 O54 112.8(4) . . ?
O53 S51 O52 109.8(4) . . ?
O54 S51 O52 110.5(4) . . ?
O53 S51 O55 111.0(4) . . ?
O54 S51 O55 109.5(4) . . ?
O52 S51 O55 102.9(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
N1 C1 C2 C3 1.4(12) . . . . ?
C1 C2 C3 C4 -0.6(12) . . . . ?
C2 C3 C4 C5 -0.5(12) . . . . ?
C3 C4 C5 N1 0.8(12) . . . . ?
C3 C4 C5 C6 -178.8(7) . . . . ?
N1 C5 C6 N2 -0.8(9) . . . . ?
C4 C5 C6 N2 178.9(7) . . . . ?
N2 C7 C8 C9 -0.8(12) . . . . ?
N2 C7 C8 C12 178.9(7) . . . . ?
C7 C8 C9 O1 -1.9(12) . . . . ?
C12 C8 C9 O1 178.5(7) . . . . ?
C7 C8 C9 O2 175.8(7) . . . . ?
C12 C8 C9 O2 -3.9(11) . . . . ?
C7 C8 C12 O3 -17.2(11) . . . . ?
C9 C8 C12 O3 162.4(8) . . . . ?
C7 C8 C12 O4 160.7(6) . . . . ?
C9 C8 C12 O4 -19.6(11) . . . . ?
N21 C21 C22 C23 -0.5(12) . . . . ?
C21 C22 C23 C24 0.5(13) . . . . ?
C22 C23 C24 C25 -0.3(12) . . . . ?
C23 C24 C25 N21 0.3(12) . . . . ?
C23 C24 C25 C26 178.0(8) . . . . ?
N21 C25 C26 N22 -3.2(10) . . . . ?
C24 C25 C26 N22 179.1(7) . . . . ?
N22 C27 C28 C29 -0.5(13) . . . . ?
N22 C27 C28 C32 177.4(8) . . . . ?
C27 C28 C29 O21 5.1(12) . . . . ?
C32 C28 C29 O21 -172.7(7) . . . . ?
C27 C28 C29 O22 -175.8(7) . . . . ?
C32 C28 C29 O22 6.4(12) . . . . ?
C27 C28 C32 O23 -7.0(12) . . . . ?
C29 C28 C32 O23 170.8(8) . . . . ?
C27 C28 C32 O24 172.8(7) . . . . ?
C29 C28 C32 O24 -9.3(12) . . . . ?
C4 C5 N1 C1 -0.1(11) . . . . ?
C6 C5 N1 C1 179.5(7) . . . . ?
C4 C5 N1 Cu1 179.0(6) . . . . ?
C6 C5 N1 Cu1 -1.4(8) . . . . ?
C2 C1 N1 C5 -1.0(11) . . . . ?
C2 C1 N1 Cu1 -180.0(6) . . . . ?
C8 C7 N2 C6 177.6(7) . . . . ?
C8 C7 N2 Cu1 3.0(11) . . . . ?
C5 C6 N2 C7 -172.5(6) . . . . ?
C5 C6 N2 Cu1 2.7(8) . . . . ?
C24 C25 N21 C21 -0.4(11) . . . . ?
C26 C25 N21 C21 -178.2(7) . . . . ?
C24 C25 N21 Cu2 178.6(6) . . . . ?
C26 C25 N21 Cu2 0.8(9) . . . . ?
C22 C21 N21 C25 0.5(12) . . . . ?
C22 C21 N21 Cu2 -178.4(6) . . . . ?
C28 C27 N22 C26 178.0(7) . . . . ?
C28 C27 N22 Cu2 -5.4(12) . . . . ?
C25 C26 N22 C27 -178.8(7) . . . . ?
C25 C26 N22 Cu2 4.2(8) . . . . ?
O2 C9 O1 Cu1 -175.4(5) . . . . ?
C8 C9 O1 Cu1 2.2(12) . . . . ?
O1 C9 O2 C10 -2.9(11) . . . . ?
C8 C9 O2 C10 179.3(7) . . . . ?
C11 C10 O2 C9 -81.0(10) . . . . ?
O3 C12 O4 C13 -2.1(11) . . . . ?
C8 C12 O4 C13 179.9(6) . . . . ?
C14 C13 O4 C12 170.9(7) . . . . ?
O22 C29 O21 Cu2 177.5(5) . . . . ?
C28 C29 O21 Cu2 -3.4(12) . . . . ?
O21 C29 O22 C30 -2.4(10) . . . . ?
C28 C29 O22 C30 178.5(7) . . . . ?
C31 C30 O22 C29 -176.0(7) . . . . ?
O23 C32 O24 C33 -3.9(11) . . . . ?
C28 C32 O24 C33 176.3(7) . . . . ?
C34 C33 O24 C32 -178.4(8) . . . . ?
C7 N2 Cu1 O52 -136.2(15) . . . . ?
C6 N2 Cu1 O52 49.1(18) . . . . ?
C7 N2 Cu1 O1 -2.2(7) . . . . ?
C6 N2 Cu1 O1 -176.9(5) . . . . ?
C7 N2 Cu1 N1 171.9(7) . . . . ?
C6 N2 Cu1 N1 -2.8(5) . . . . ?
C29 O21 Cu2 N22 -1.2(7) . . . . ?
C29 O21 Cu2 O55 172.6(7) . . . . ?
Cu1 O52 S51 O53 60.6(6) . . . . ?
Cu1 O52 S51 O54 -64.4(6) . . . . ?
Cu1 O52 S51 O55 178.8(5) . . . . ?
Cu2 O55 S51 O53 -82.2(6) . . . . ?
Cu2 O55 S51 O54 42.9(6) . . . . ?
Cu2 O55 S51 O52 160.4(5) . . . . ?

_refine_diff_density_max         1.773
_refine_diff_density_min         -3.484
_refine_diff_density_rms         0.261

