# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1567430'
_audit_update_record             
;
2017-08-08 deposited with the CCDC.
2017-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H20 Cl2 Cu N6 O9.50'
_chemical_formula_weight         702.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'

_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'
'-y+3/4, x+1/4, z+1/4'
'-x+1/2, -y, z+1/2'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'-x+1, -y+1/2, z+1'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'y-3/4, -x-1/4, -z-1/4'
'x-1/2, y, -z-1/2'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'x, y+1/2, -z'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   20.7098(11)
_cell_length_b                   20.7098(11)
_cell_length_c                   27.0998(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     11623.0(14)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6689
_cell_measurement_theta_min      3.162
_cell_measurement_theta_max      28.691

_exptl_crystal_description       cube
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_F_000             5712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.38
_exptl_absorpt_coefficient_mu    1.001
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  EOS,Gemini
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14288
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.162
_diffrn_reflns_theta_max         28.691
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6689
_reflns_number_gt                3749
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1454P)²+32.7795P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6689
_refine_ls_number_parameters     402
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1496
_refine_ls_R_factor_gt           0.0858
_refine_ls_wR_factor_ref         0.2920
_refine_ls_wR_factor_gt          0.2371
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.25378(3) 0.50590(3) 0.37957(3) 0.0395(3) Uani 1 1 d . . . . .
Cl1 Cl 0.63528(11) 0.35131(10) 0.51752(8) 0.0773(6) Uani 1 1 d . . . . .
Cl2 Cl 0.14572(12) 0.36762(11) 0.48512(8) 0.0851(7) Uani 1 1 d . . . . .
O1 O 0.2558(3) 0.5065(3) 0.45767(19) 0.0644(14) Uani 1 1 d . . . . .
N4 N 0.3466(2) 0.4817(2) 0.38034(16) 0.0404(10) Uani 1 1 d . . . . .
N3 N 0.2164(2) 0.4295(2) 0.34163(17) 0.0473(11) Uani 1 1 d . . . . .
N1 N 0.1611(2) 0.5305(2) 0.38225(16) 0.0414(10) Uani 1 1 d . . . . .
C9 C 0.1512(3) 0.4314(3) 0.3392(2) 0.0528(15) Uani 1 1 d . . . . .
N6 N 0.2912(2) 0.5842(2) 0.34329(17) 0.0465(11) Uani 1 1 d . . . . .
N5 N 0.4803(3) 0.4631(3) 0.3808(2) 0.0711(17) Uani 1 1 d . . . . .
N2 N 0.0279(3) 0.5489(3) 0.3828(2) 0.0712(17) Uani 1 1 d . . . . .
C2 C 0.1749(3) 0.6303(3) 0.4270(2) 0.0503(14) Uani 1 1 d . . . . .
H2 H 0.2193 0.6240 0.4285 0.060 Uiso 1 1 calc R U . . .
C21 C 0.3858(3) 0.5243(3) 0.3610(2) 0.0492(14) Uani 1 1 d . . . . .
C26 C 0.2595(4) 0.6339(3) 0.3236(2) 0.0650(18) Uani 1 1 d . . . . .
H26 H 0.2146 0.6345 0.3252 0.078 Uiso 1 1 calc R U . . .
C8 C 0.1219(3) 0.4883(3) 0.3620(2) 0.0489(14) Uani 1 1 d . . . . .
C7 C 0.0539(3) 0.4979(4) 0.3634(3) 0.0690(19) Uani 1 1 d . . . . .
H7 H 0.0272 0.4664 0.3499 0.083 Uiso 1 1 calc R U . . .
C4 C 0.0807(4) 0.6948(4) 0.4453(3) 0.074(2) Uani 1 1 d . . . . .
H4 H 0.0630 0.7321 0.4588 0.089 Uiso 1 1 calc R U . . .
O7 O 0.1146(5) 0.3520(4) 0.5261(4) 0.176(4) Uani 1 1 d . . . . .
C6 C 0.0683(3) 0.5942(3) 0.4031(2) 0.0563(16) Uani 1 1 d . . . . .
C16 C 0.3607(4) 0.3247(3) 0.4423(2) 0.0618(17) Uani 1 1 d . . . . .
H16 H 0.3348 0.2935 0.4571 0.074 Uiso 1 1 calc R U . . .
C17 C 0.4275(4) 0.3162(4) 0.4399(3) 0.073(2) Uani 1 1 d . . . . .
H17 H 0.4456 0.2785 0.4524 0.088 Uiso 1 1 calc R U . . .
C23 C 0.3895(4) 0.6314(4) 0.3182(3) 0.076(2) Uani 1 1 d . . . . .
H23 H 0.4343 0.6302 0.3163 0.091 Uiso 1 1 calc R U . . .
C14 C 0.3730(3) 0.4264(3) 0.4009(2) 0.0455(13) Uani 1 1 d . . . . .
C1 C 0.1355(3) 0.5845(3) 0.40401(19) 0.0428(13) Uani 1 1 d . . . . .
C18 C 0.4661(4) 0.3607(4) 0.4202(3) 0.072(2) Uani 1 1 d . . . . .
H18 H 0.5105 0.3542 0.4195 0.087 Uiso 1 1 calc R U . . .
C19 C 0.4396(3) 0.4176(3) 0.4004(2) 0.0536(15) Uani 1 1 d . . . . .
C25 C 0.2911(5) 0.6844(4) 0.3010(3) 0.077(2) Uani 1 1 d . . . . .
H25 H 0.2677 0.7182 0.2873 0.093 Uiso 1 1 calc R U . . .
C3 C 0.1477(4) 0.6850(3) 0.4475(2) 0.0627(18) Uani 1 1 d . . . . .
H3 H 0.1739 0.7154 0.4629 0.075 Uiso 1 1 calc R U . . .
C24 C 0.3545(5) 0.6845(4) 0.2988(3) 0.086(3) Uani 1 1 d . . . . .
H24 H 0.3763 0.7191 0.2847 0.103 Uiso 1 1 calc R U . . .
C12 C 0.2165(5) 0.3309(4) 0.2973(3) 0.080(2) Uani 1 1 d . . . . .
H12 H 0.2398 0.2976 0.2829 0.096 Uiso 1 1 calc R U . . .
C13 C 0.2481(4) 0.3810(3) 0.3202(2) 0.0614(17) Uani 1 1 d . . . . .
H13 H 0.2930 0.3812 0.3207 0.074 Uiso 1 1 calc R U . . .
C10 C 0.1169(4) 0.3822(4) 0.3170(3) 0.084(2) Uani 1 1 d . . . . .
H10 H 0.0720 0.3831 0.3159 0.101 Uiso 1 1 calc R U . . .
C20 C 0.4541(3) 0.5141(4) 0.3621(3) 0.0627(17) Uani 1 1 d . . . . .
H20 H 0.4808 0.5456 0.3488 0.075 Uiso 1 1 calc R U . . .
C11 C 0.1519(5) 0.3304(4) 0.2960(3) 0.094(3) Uani 1 1 d . . . . .
H11 H 0.1301 0.2962 0.2813 0.112 Uiso 1 1 calc R U . . .
C5 C 0.0421(3) 0.6514(4) 0.4241(3) 0.068(2) Uani 1 1 d . . . . .
H5 H -0.0022 0.6585 0.4231 0.081 Uiso 1 1 calc R U . . .
C22 C 0.3562(3) 0.5823(3) 0.3398(2) 0.0480(14) Uani 1 1 d . . . . .
C15 C 0.3333(3) 0.3795(3) 0.4226(2) 0.0526(15) Uani 1 1 d . . . . .
H15 H 0.2888 0.3854 0.4237 0.063 Uiso 1 1 calc R U . . .
O6 O 0.2036(5) 0.4021(8) 0.5073(4) 0.238(7) Uani 1 1 d . . . . .
O2 O 0.6613(12) 0.3555(8) 0.4777(5) 0.455(19) Uani 1 1 d . . . . .
O4 O 0.6614(6) 0.3058(5) 0.5482(5) 0.214(5) Uani 1 1 d . . . . .
O5 O 0.5821(12) 0.3302(12) 0.5004(9) 0.376(11) Uiso 1 1 d . . . . .
O9 O 0.1226(6) 0.4160(5) 0.4601(4) 0.202(5) Uani 1 1 d . . . . .
O3 O 0.6237(7) 0.4068(4) 0.5373(3) 0.208(6) Uani 1 1 d . . . . .
O8 O 0.1703(7) 0.3186(6) 0.4577(5) 0.255(7) Uani 1 1 d . . . . .
O10 O 0.0000 0.2500 0.3775(9) 0.38(2) Uiso 1 2 d S . P . .
H55A H 0.240(4) 0.478(5) 0.471(4) 0.10(4) Uiso 1 1 d . . . . .
H55B H 0.285(4) 0.525(4) 0.478(3) 0.08(3) 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
Cu1 N1 1.987(4) . ?
Cu1 N4 1.987(4) . ?
Cu1 N3 2.040(5) . ?
Cu1 N6 2.048(5) . ?
Cu1 O1 2.117(5) . ?
Cl1 O2 1.209(10) . ?
Cl1 O5 1.27(2) . ?
Cl1 O3 1.289(8) . ?
Cl1 O4 1.368(7) . ?
Cl2 O9 1.301(8) . ?
Cl2 O7 1.325(8) . ?
Cl2 O8 1.356(9) . ?
Cl2 O6 1.519(13) . ?
N4 C21 1.309(7) . ?
N4 C14 1.386(7) . ?
N3 C13 1.333(8) . ?
N3 C9 1.353(7) . ?
N1 C8 1.315(7) . ?
N1 C1 1.371(7) . ?
C9 C10 1.378(9) . ?
C9 C8 1.463(9) . ?
N6 C26 1.332(8) . ?
N6 C22 1.349(7) . ?
N5 C20 1.291(9) . ?
N5 C19 1.371(9) . ?
N2 C7 1.297(9) . ?
N2 C6 1.373(9) . ?
C2 C3 1.381(8) . ?
C2 C1 1.398(8) . ?
C21 C20 1.429(8) . ?
C21 C22 1.467(8) . ?
C26 C25 1.379(10) . ?
C8 C7 1.422(9) . ?
C4 C5 1.334(11) . ?
C4 C3 1.404(10) . ?
C6 C1 1.405(8) . ?
C6 C5 1.422(9) . ?
C16 C15 1.377(8) . ?
C16 C17 1.397(10) . ?
C17 C18 1.332(11) . ?
C23 C22 1.361(9) . ?
C23 C24 1.417(11) . ?
C14 C19 1.392(8) . ?
C14 C15 1.402(8) . ?
C18 C19 1.404(9) . ?
C25 C24 1.314(12) . ?
C12 C11 1.338(12) . ?
C12 C13 1.375(10) . ?
C10 C11 1.414(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 Cu1 N4 177.3(2) . . ?
N1 Cu1 N3 81.44(19) . . ?
N4 Cu1 N3 100.16(18) . . ?
N1 Cu1 N6 100.36(18) . . ?
N4 Cu1 N6 80.72(19) . . ?
N3 Cu1 N6 121.1(2) . . ?
N1 Cu1 O1 88.93(19) . . ?
N4 Cu1 O1 88.4(2) . . ?
N3 Cu1 O1 121.0(2) . . ?
N6 Cu1 O1 117.9(2) . . ?
O2 Cl1 O5 94.9(15) . . ?
O2 Cl1 O3 112.9(9) . . ?
O5 Cl1 O3 107.3(13) . . ?
O2 Cl1 O4 114.6(9) . . ?
O5 Cl1 O4 109.1(12) . . ?
O3 Cl1 O4 115.7(8) . . ?
O9 Cl2 O7 116.5(8) . . ?
O9 Cl2 O8 115.4(9) . . ?
O7 Cl2 O8 117.4(7) . . ?
O9 Cl2 O6 97.8(7) . . ?
O7 Cl2 O6 99.6(7) . . ?
O8 Cl2 O6 105.8(9) . . ?
C21 N4 C14 118.3(5) . . ?
C21 N4 Cu1 115.2(4) . . ?
C14 N4 Cu1 126.5(4) . . ?
C13 N3 C9 119.5(5) . . ?
C13 N3 Cu1 128.1(4) . . ?
C9 N3 Cu1 112.4(4) . . ?
C8 N1 C1 118.9(5) . . ?
C8 N1 Cu1 114.3(4) . . ?
C1 N1 Cu1 126.8(4) . . ?
N3 C9 C10 120.9(6) . . ?
N3 C9 C8 114.6(5) . . ?
C10 C9 C8 124.5(6) . . ?
C26 N6 C22 119.1(5) . . ?
C26 N6 Cu1 128.1(4) . . ?
C22 N6 Cu1 112.9(4) . . ?
C20 N5 C19 117.1(6) . . ?
C7 N2 C6 117.7(6) . . ?
C3 C2 C1 119.9(6) . . ?
N4 C21 C20 120.4(6) . . ?
N4 C21 C22 116.7(5) . . ?
C20 C21 C22 122.9(6) . . ?
N6 C26 C25 122.0(7) . . ?
N1 C8 C7 120.5(6) . . ?
N1 C8 C9 117.2(5) . . ?
C7 C8 C9 122.3(6) . . ?
N2 C7 C8 122.4(7) . . ?
C5 C4 C3 120.9(7) . . ?
N2 C6 C1 120.9(6) . . ?
N2 C6 C5 119.8(6) . . ?
C1 C6 C5 119.3(7) . . ?
C15 C16 C17 119.6(7) . . ?
C18 C17 C16 121.7(7) . . ?
C22 C23 C24 118.7(7) . . ?
N4 C14 C19 119.7(6) . . ?
N4 C14 C15 120.7(5) . . ?
C19 C14 C15 119.7(5) . . ?
N1 C1 C2 121.2(5) . . ?
N1 C1 C6 119.5(5) . . ?
C2 C1 C6 119.3(5) . . ?
C17 C18 C19 120.0(7) . . ?
N5 C19 C14 121.5(6) . . ?
N5 C19 C18 119.0(6) . . ?
C14 C19 C18 119.5(7) . . ?
C24 C25 C26 119.8(7) . . ?
C2 C3 C4 120.3(7) . . ?
C25 C24 C23 119.5(7) . . ?
C11 C12 C13 119.6(8) . . ?
N3 C13 C12 122.0(7) . . ?
C9 C10 C11 118.1(7) . . ?
N5 C20 C21 123.0(6) . . ?
C12 C11 C10 119.7(7) . . ?
C4 C5 C6 120.3(7) . . ?
N6 C22 C23 121.0(6) . . ?
N6 C22 C21 114.4(5) . . ?
C23 C22 C21 124.6(6) . . ?
C16 C15 C14 119.5(6) . . ?

_refine_diff_density_max         1.385
_refine_diff_density_min         -0.721
_refine_diff_density_rms         0.109

_shelxl_version_number           2013-4

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

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1567435'
_audit_update_record             
;
2017-08-08 deposited with the CCDC.
2017-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 Cu N2 O7'
_chemical_formula_weight         401.85

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

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

_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                   8.0993(6)
_cell_length_b                   10.3092(6)
_cell_length_c                   11.0759(8)
_cell_angle_alpha                96.292(5)
_cell_angle_beta                 107.070(7)
_cell_angle_gamma                108.306(6)
_cell_volume                     818.32(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3317
_cell_measurement_theta_min      3.213
_cell_measurement_theta_max      26.372

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_F_000             414
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.38
_exptl_absorpt_coefficient_mu    1.376
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  EOS,Gemini
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5194
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.213
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3317
_reflns_number_gt                2824
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0654P)²+0.2399P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3317
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1333
_refine_ls_wR_factor_gt          0.1255
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.05551(5) 0.72449(4) 0.64579(4) 0.02743(17) Uani 1 1 d . . . . .
O1 O 0.2372(3) 0.8652(3) 0.5932(2) 0.0306(6) Uani 1 1 d . . . . .
O2 O 0.2898(3) 0.8289(3) 0.7883(2) 0.0323(6) Uani 1 1 d . . . . .
O3 O 0.5144(3) 0.9889(3) 0.7449(2) 0.0377(6) Uani 1 1 d . . . . .
O4 O -0.0939(4) 0.8458(3) 0.7068(3) 0.0423(7) Uani 1 1 d . . . . .
H6A H -0.1459 0.8076 0.7589 0.063 Uiso 1 1 d R U . . .
H6B H -0.1798 0.8496 0.6400 0.063 Uiso 1 1 d R U . . .
N1 N -0.1674(4) 0.6072(3) 0.4893(3) 0.0260(6) Uani 1 1 d . . . . .
O5 O -0.3339(3) 0.9422(3) 0.5579(3) 0.0437(7) Uani 1 1 d G . . . .
H23A H -0.3888 0.9646 0.6067 0.066 Uiso 1 1 d G U . . .
H23B H -0.3120 1.0035 0.5134 0.066 Uiso 1 1 d G U . . .
O6 O 0.7446(3) 1.0368(4) 0.9911(3) 0.0534(9) Uani 1 1 d G . . . .
H24A H 0.6650 1.0190 0.9157 0.080 Uiso 1 1 d G U . . .
H24B H 0.7086 1.0732 1.0463 0.080 Uiso 1 1 d G U . . .
N2 N -0.0185(4) 0.5524(3) 0.7123(3) 0.0302(7) Uani 1 1 d . . . . .
O7 O 1.1216(4) 1.1830(3) 1.0526(3) 0.0507(8) Uani 1 1 d G . . . .
H25A H 1.1681 1.1292 1.0228 0.076 Uiso 1 1 d G U . . .
H25B H 1.0039 1.1452 1.0221 0.076 Uiso 1 1 d G U . . .
C5 C -0.2403(5) 0.6470(4) 0.3766(3) 0.0275(8) Uani 1 1 d . . . . .
C6 C -0.4027(5) 0.5530(4) 0.2772(4) 0.0330(8) Uani 1 1 d . . . . .
C10 C -0.1739(5) 0.4491(4) 0.6307(3) 0.0279(8) Uani 1 1 d . . . . .
C8 C -0.4215(5) 0.3856(4) 0.4109(4) 0.0351(9) Uani 1 1 d . . . . .
H9 H -0.4812 0.2991 0.4258 0.042 Uiso 1 1 calc R U . . .
C14 C 0.0727(5) 0.5333(4) 0.8267(4) 0.0365(9) Uani 1 1 d . . . . .
H22 H 0.1802 0.6052 0.8820 0.044 Uiso 1 1 calc R U . . .
C3 C -0.2249(5) 0.8211(4) 0.2487(4) 0.0384(9) Uani 1 1 d . . . . .
H14 H -0.1669 0.9104 0.2383 0.046 Uiso 1 1 calc R U . . .
C15 C 0.3557(4) 0.8997(4) 0.7111(3) 0.0267(8) Uani 1 1 d . . . . .
C4 C -0.1522(5) 0.7826(4) 0.3603(4) 0.0328(8) Uani 1 1 d . . . . .
H15 H -0.0454 0.8452 0.4253 0.039 Uiso 1 1 calc R U . . .
C9 C -0.2574(5) 0.4818(4) 0.5051(3) 0.0273(8) Uani 1 1 d . . . . .
C7 C -0.4921(5) 0.4213(4) 0.2970(4) 0.0389(9) Uani 1 1 d . . . . .
H10 H -0.5994 0.3582 0.2327 0.047 Uiso 1 1 calc R U . . .
C12 C -0.1502(6) 0.3044(4) 0.7832(4) 0.0417(10) Uani 1 1 d . . . . .
H20 H -0.1951 0.2207 0.8079 0.050 Uiso 1 1 calc R U . . .
C13 C 0.0107(6) 0.4093(4) 0.8643(4) 0.0402(9) Uani 1 1 d . . . . .
H21 H 0.0768 0.3967 0.9435 0.048 Uiso 1 1 calc R U . . .
C11 C -0.2451(5) 0.3236(4) 0.6648(4) 0.0372(9) Uani 1 1 d . . . . .
H19 H -0.3545 0.2537 0.6092 0.045 Uiso 1 1 calc R U . . .
C1 C -0.4716(6) 0.5980(5) 0.1624(4) 0.0418(10) Uani 1 1 d . . . . .
H12 H -0.5773 0.5373 0.0953 0.050 Uiso 1 1 calc R U . . .
C2 C -0.3838(6) 0.7293(5) 0.1503(4) 0.0450(10) Uani 1 1 d . . . . .
H13 H -0.4308 0.7579 0.0750 0.054 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 O2 1.959(2) . ?
Cu1 N2 1.981(3) . ?
Cu1 O1 1.989(2) . ?
Cu1 N1 2.014(3) . ?
Cu1 O4 2.175(3) . ?
Cu1 C15 2.371(3) . ?
O1 C15 1.304(4) . ?
O2 C15 1.307(4) . ?
O3 C15 1.240(4) . ?
O4 H6A 0.8681 . ?
O4 H6B 0.8682 . ?
N1 C9 1.329(4) . ?
N1 C5 1.381(4) . ?
O5 H23A 0.8500 . ?
O5 H23B 0.8499 . ?
O6 H24A 0.8500 . ?
O6 H24B 0.8499 . ?
N2 C14 1.338(5) . ?
N2 C10 1.347(5) . ?
O7 H25A 0.8502 . ?
O7 H25B 0.8499 . ?
C5 C6 1.413(5) . ?
C5 C4 1.414(5) . ?
C6 C7 1.399(6) . ?
C6 C1 1.420(5) . ?
C10 C11 1.384(5) . ?
C10 C9 1.483(5) . ?
C8 C7 1.366(6) . ?
C8 C9 1.403(5) . ?
C8 H9 0.9300 . ?
C14 C13 1.377(5) . ?
C14 H22 0.9300 . ?
C3 C4 1.363(5) . ?
C3 C2 1.388(6) . ?
C3 H14 0.9300 . ?
C4 H15 0.9300 . ?
C7 H10 0.9300 . ?
C12 C13 1.375(6) . ?
C12 C11 1.383(6) . ?
C12 H20 0.9300 . ?
C13 H21 0.9300 . ?
C11 H19 0.9300 . ?
C1 C2 1.360(6) . ?
C1 H12 0.9300 . ?
C2 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 N2 97.96(11) . . ?
O2 Cu1 O1 66.83(10) . . ?
N2 Cu1 O1 150.85(12) . . ?
O2 Cu1 N1 173.01(10) . . ?
N2 Cu1 N1 81.89(12) . . ?
O1 Cu1 N1 110.16(11) . . ?
O2 Cu1 O4 94.46(11) . . ?
N2 Cu1 O4 103.72(12) . . ?
O1 Cu1 O4 102.21(11) . . ?
N1 Cu1 O4 92.36(11) . . ?
O2 Cu1 C15 33.46(10) . . ?
N2 Cu1 C15 127.17(12) . . ?
O1 Cu1 C15 33.37(10) . . ?
N1 Cu1 C15 143.13(12) . . ?
O4 Cu1 C15 100.30(12) . . ?
C15 O1 Cu1 89.6(2) . . ?
C15 O2 Cu1 90.83(19) . . ?
Cu1 O4 H6A 110.5 . . ?
Cu1 O4 H6B 110.2 . . ?
H6A O4 H6B 108.4 . . ?
C9 N1 C5 118.8(3) . . ?
C9 N1 Cu1 113.5(2) . . ?
C5 N1 Cu1 127.5(2) . . ?
H23A O5 H23B 109.5 . . ?
H24A O6 H24B 109.5 . . ?
C14 N2 C10 120.1(3) . . ?
C14 N2 Cu1 125.6(3) . . ?
C10 N2 Cu1 114.4(2) . . ?
H25A O7 H25B 109.5 . . ?
N1 C5 C6 120.4(3) . . ?
N1 C5 C4 120.0(3) . . ?
C6 C5 C4 119.7(3) . . ?
C7 C6 C5 118.9(4) . . ?
C7 C6 C1 122.6(4) . . ?
C5 C6 C1 118.4(4) . . ?
N2 C10 C11 121.0(3) . . ?
N2 C10 C9 114.7(3) . . ?
C11 C10 C9 124.3(3) . . ?
C7 C8 C9 118.9(4) . . ?
C7 C8 H9 120.6 . . ?
C9 C8 H9 120.6 . . ?
N2 C14 C13 121.4(4) . . ?
N2 C14 H22 119.3 . . ?
C13 C14 H22 119.3 . . ?
C4 C3 C2 121.1(4) . . ?
C4 C3 H14 119.4 . . ?
C2 C3 H14 119.4 . . ?
O3 C15 O1 123.2(3) . . ?
O3 C15 O2 124.1(3) . . ?
O1 C15 O2 112.7(3) . . ?
O3 C15 Cu1 178.5(3) . . ?
O1 C15 Cu1 57.03(17) . . ?
O2 C15 Cu1 55.71(16) . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 H15 120.2 . . ?
C5 C4 H15 120.2 . . ?
N1 C9 C8 123.1(3) . . ?
N1 C9 C10 115.5(3) . . ?
C8 C9 C10 121.4(3) . . ?
C8 C7 C6 119.8(3) . . ?
C8 C7 H10 120.1 . . ?
C6 C7 H10 120.1 . . ?
C13 C12 C11 119.8(4) . . ?
C13 C12 H20 120.1 . . ?
C11 C12 H20 120.1 . . ?
C12 C13 C14 119.1(4) . . ?
C12 C13 H21 120.5 . . ?
C14 C13 H21 120.5 . . ?
C12 C11 C10 118.6(4) . . ?
C12 C11 H19 120.7 . . ?
C10 C11 H19 120.7 . . ?
C2 C1 C6 120.3(4) . . ?
C2 C1 H12 119.8 . . ?
C6 C1 H12 119.8 . . ?
C1 C2 C3 120.8(4) . . ?
C1 C2 H13 119.6 . . ?
C3 C2 H13 119.6 . . ?

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
C9 N1 C5 C6 -3.3(5) . . . . ?
Cu1 N1 C5 C6 -177.6(2) . . . . ?
C9 N1 C5 C4 176.8(3) . . . . ?
Cu1 N1 C5 C4 2.5(5) . . . . ?
N1 C5 C6 C7 2.6(5) . . . . ?
C4 C5 C6 C7 -177.5(3) . . . . ?
N1 C5 C6 C1 -179.3(3) . . . . ?
C4 C5 C6 C1 0.6(5) . . . . ?
C14 N2 C10 C11 2.0(5) . . . . ?
Cu1 N2 C10 C11 -178.6(3) . . . . ?
C14 N2 C10 C9 -177.7(3) . . . . ?
Cu1 N2 C10 C9 1.6(4) . . . . ?
C10 N2 C14 C13 -0.4(6) . . . . ?
Cu1 N2 C14 C13 -179.7(3) . . . . ?
Cu1 O1 C15 O3 178.2(3) . . . . ?
Cu1 O1 C15 O2 -0.9(3) . . . . ?
Cu1 O2 C15 O3 -178.2(3) . . . . ?
Cu1 O2 C15 O1 0.9(3) . . . . ?
C2 C3 C4 C5 -0.2(6) . . . . ?
N1 C5 C4 C3 179.8(3) . . . . ?
C6 C5 C4 C3 0.0(5) . . . . ?
C5 N1 C9 C8 1.8(5) . . . . ?
Cu1 N1 C9 C8 176.8(3) . . . . ?
C5 N1 C9 C10 -177.7(3) . . . . ?
Cu1 N1 C9 C10 -2.7(4) . . . . ?
C7 C8 C9 N1 0.6(6) . . . . ?
C7 C8 C9 C10 -180.0(3) . . . . ?
N2 C10 C9 N1 0.7(5) . . . . ?
C11 C10 C9 N1 -179.0(3) . . . . ?
N2 C10 C9 C8 -178.8(3) . . . . ?
C11 C10 C9 C8 1.5(5) . . . . ?
C9 C8 C7 C6 -1.3(6) . . . . ?
C5 C6 C7 C8 -0.2(6) . . . . ?
C1 C6 C7 C8 -178.2(4) . . . . ?
C11 C12 C13 C14 1.2(6) . . . . ?
N2 C14 C13 C12 -1.2(6) . . . . ?
C13 C12 C11 C10 0.4(6) . . . . ?
N2 C10 C11 C12 -2.0(6) . . . . ?
C9 C10 C11 C12 177.7(3) . . . . ?
C7 C6 C1 C2 177.2(4) . . . . ?
C5 C6 C1 C2 -0.8(6) . . . . ?
C6 C1 C2 C3 0.6(6) . . . . ?
C4 C3 C2 C1 -0.1(7) . . . . ?

_refine_diff_density_max         1.235
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.096

_shelxl_version_number           2013-4

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

data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1567437'
_audit_update_record             
;
2017-08-08 deposited with the CCDC.
2017-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H26 Cl Cu N6 O4'
_chemical_formula_weight         633.56

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'
Cl Cl 0.1484 0.1585 '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                   14.5802(11)
_cell_length_b                   14.7784(8)
_cell_length_c                   14.3077(11)
_cell_angle_alpha                90
_cell_angle_beta                 114.588(9)
_cell_angle_gamma                90
_cell_volume                     2803.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2858
_cell_measurement_theta_min      3.132
_cell_measurement_theta_max      26.370

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_F_000             1304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_exptl_absorpt_coefficient_mu    0.923
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  EOS,Gemini
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6239
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.132
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2858
_reflns_number_gt                2301
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1568P)²+5.2328P] 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         2858
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0757
_refine_ls_wR_factor_ref         0.2349
_refine_ls_wR_factor_gt          0.2196
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.78461(6) 0.2500 0.0518(3) Uani 1 2 d S T P . .
Cl1 Cl 0.5000 0.11777(13) 0.2500 0.0619(5) Uani 1 2 d S T P . .
N3 N 0.5978(3) 0.8245(3) 0.1940(3) 0.0487(9) Uani 1 1 d . . . . .
N1 N 0.6235(3) 0.7123(2) 0.3466(3) 0.0400(7) Uani 1 1 d . . . . .
N2 N 0.8072(3) 0.6220(3) 0.4573(3) 0.0559(10) Uani 1 1 d . . . . .
C1 C 0.6375(3) 0.6617(3) 0.4315(3) 0.0410(9) Uani 1 1 d . . . . .
C8 C 0.7287(3) 0.6154(3) 0.4857(3) 0.0503(11) Uani 1 1 d . . . . .
C2 C 0.5607(3) 0.6564(3) 0.4666(4) 0.0485(10) Uani 1 1 d . . . . .
H2 H 0.5003 0.6870 0.4311 0.058 Uiso 1 1 calc R U . . .
C10 C 0.7010(3) 0.7188(3) 0.3210(3) 0.0425(9) Uani 1 1 d . . . . .
C9 C 0.7919(3) 0.6726(3) 0.3774(4) 0.0529(11) Uani 1 1 d . . . . .
H9 H 0.8441 0.6786 0.3566 0.064 Uiso 1 1 calc R U . . .
C11 C 0.6836(3) 0.7760(3) 0.2292(3) 0.0469(10) Uani 1 1 d . . . . .
C6 C 0.6637(5) 0.5568(3) 0.6039(4) 0.0597(13) Uani 1 1 d . . . . .
C3 C 0.5737(4) 0.6065(3) 0.5529(4) 0.0541(11) Uani 1 1 d . . . . .
C5 C 0.6774(6) 0.4973(4) 0.6948(5) 0.086(2) Uani 1 1 d . . . . .
H5A H 0.6180 0.5004 0.7079 0.129 Uiso 1 1 calc R U . . .
H5B H 0.7346 0.5179 0.7543 0.129 Uiso 1 1 calc R U . . .
H5C H 0.6883 0.4359 0.6799 0.129 Uiso 1 1 calc R U . . .
C7 C 0.7396(4) 0.5627(3) 0.5716(4) 0.0579(13) Uani 1 1 d . . . . .
H7 H 0.7994 0.5314 0.6070 0.070 Uiso 1 1 calc R U . . .
C13 C 0.7231(6) 0.8321(6) 0.0933(5) 0.087(2) Uani 1 1 d . . . . .
H13 H 0.7631 0.8327 0.0569 0.105 Uiso 1 1 calc R U . . .
C15 C 0.5770(4) 0.8777(4) 0.1109(4) 0.0664(14) Uani 1 1 d . . . . .
H15 H 0.5179 0.9116 0.0862 0.080 Uiso 1 1 calc R U . . .
C12 C 0.7490(5) 0.7776(4) 0.1812(5) 0.0713(15) Uani 1 1 d . . . . .
H12 H 0.8081 0.7437 0.2063 0.086 Uiso 1 1 calc R U . . .
C14 C 0.6388(6) 0.8836(5) 0.0623(5) 0.0821(19) Uani 1 1 d . . . . .
H14 H 0.6234 0.9233 0.0073 0.099 Uiso 1 1 calc R U . . .
C4 C 0.4908(5) 0.6071(4) 0.5905(5) 0.0743(16) Uani 1 1 d . . . . .
H4A H 0.5099 0.5693 0.6502 0.111 Uiso 1 1 calc R U . . .
H4B H 0.4295 0.5847 0.5373 0.111 Uiso 1 1 calc R U . . .
H4C H 0.4804 0.6679 0.6079 0.111 Uiso 1 1 calc R U . . .
O1 O 0.4845(13) 0.1895(11) 0.1880(10) 0.273(7) Uani 1 1 d . . . . .
O2 O 0.4234(14) 0.0852(10) 0.247(2) 0.452(17) 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
Cu1 N3 1.994(4) . ?
Cu1 N3 1.994(4) 2_655 ?
Cu1 N1 2.055(3) . ?
Cu1 N1 2.055(3) 2_655 ?
Cl1 O2 1.199(8) 2_655 ?
Cl1 O2 1.199(8) . ?
Cl1 O1 1.340(12) 2_655 ?
Cl1 O1 1.340(12) . ?
N3 C11 1.345(6) . ?
N3 C15 1.350(6) . ?
N1 C10 1.329(6) . ?
N1 C1 1.368(5) . ?
N2 C9 1.305(7) . ?
N2 C8 1.368(6) . ?
C1 C2 1.406(6) . ?
C1 C8 1.407(6) . ?
C8 C7 1.406(7) . ?
C2 C3 1.383(6) . ?
C10 C9 1.409(6) . ?
C10 C11 1.492(7) . ?
C11 C12 1.389(7) . ?
C6 C7 1.368(8) . ?
C6 C3 1.413(8) . ?
C6 C5 1.512(7) . ?
C3 C4 1.514(8) . ?
C13 C14 1.354(11) . ?
C13 C12 1.406(10) . ?
C15 C14 1.350(9) . ?
O1 O1 1.64(3) 2_655 ?

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
N3 Cu1 N3 145.6(2) . 2_655 ?
N3 Cu1 N1 81.45(15) . . ?
N3 Cu1 N1 117.15(15) 2_655 . ?
N3 Cu1 N1 117.15(15) . 2_655 ?
N3 Cu1 N1 81.45(15) 2_655 2_655 ?
N1 Cu1 N1 117.37(18) . 2_655 ?
O2 Cl1 O2 132.6(15) 2_655 . ?
O2 Cl1 O1 113.2(15) 2_655 2_655 ?
O2 Cl1 O1 104.0(10) . 2_655 ?
O2 Cl1 O1 104.0(10) 2_655 . ?
O2 Cl1 O1 113.2(15) . . ?
O1 Cl1 O1 75.5(14) 2_655 . ?
C11 N3 C15 118.2(4) . . ?
C11 N3 Cu1 113.6(3) . . ?
C15 N3 Cu1 126.2(4) . . ?
C10 N1 C1 117.0(3) . . ?
C10 N1 Cu1 112.6(3) . . ?
C1 N1 Cu1 130.3(3) . . ?
C9 N2 C8 116.3(4) . . ?
N1 C1 C2 120.0(4) . . ?
N1 C1 C8 120.9(4) . . ?
C2 C1 C8 119.1(4) . . ?
N2 C8 C7 119.7(4) . . ?
N2 C8 C1 121.1(4) . . ?
C7 C8 C1 119.2(5) . . ?
C3 C2 C1 121.0(4) . . ?
N1 C10 C9 120.8(4) . . ?
N1 C10 C11 115.5(4) . . ?
C9 C10 C11 123.6(4) . . ?
N2 C9 C10 123.8(4) . . ?
N3 C11 C12 121.9(5) . . ?
N3 C11 C10 115.0(4) . . ?
C12 C11 C10 123.0(5) . . ?
C7 C6 C3 120.0(5) . . ?
C7 C6 C5 119.5(5) . . ?
C3 C6 C5 120.5(6) . . ?
C2 C3 C6 119.4(5) . . ?
C2 C3 C4 118.8(5) . . ?
C6 C3 C4 121.8(5) . . ?
C6 C7 C8 121.2(4) . . ?
C14 C13 C12 119.0(5) . . ?
N3 C15 C14 122.6(6) . . ?
C11 C12 C13 117.9(6) . . ?
C15 C14 C13 120.2(6) . . ?
Cl1 O1 O1 52.3(7) . 2_655 ?

_refine_diff_density_max         1.058
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.110

_shelxl_version_number           2013-4

