# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1474805'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2016-12-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H32 Cl2 Cu3 N4 O12'
_chemical_formula_sum            'C32 H32 Cl2 Cu3 N4 O12'
_chemical_formula_weight         926.17

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/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                   12.979(4)
_cell_length_b                   8.793(2)
_cell_length_c                   16.272(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.842(8)
_cell_angle_gamma                90
_cell_volume                     1723.6(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3048
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_F_000             938
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    2.060
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.628
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex-II CCD'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19960
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.726
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_full        25.025
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3048
_reflns_number_gt                2693
_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       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXT (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  PLATON
_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)+(0.0686P)²+1.8124P] 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         3048
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.1208
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_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 0.5756(3) 0.2005(5) 0.4897(3) 0.0493(9) Uani 1 1 d . . . . .
C2 C 0.6266(4) 0.2898(5) 0.5721(3) 0.0601(11) Uani 1 1 d . . . . .
H2A H 0.672545 0.223336 0.619000 0.072 Uiso 1 1 calc R U . . .
H2B H 0.568388 0.330316 0.589802 0.072 Uiso 1 1 calc R U . . .
C3 C 0.6975(4) 0.4212(5) 0.5606(3) 0.0604(11) Uani 1 1 d . . . . .
H3A H 0.656924 0.474681 0.505983 0.072 Uiso 1 1 calc R U . . .
H3B H 0.712145 0.492392 0.609216 0.072 Uiso 1 1 calc R U . . .
C4 C 0.8876(3) 0.4517(4) 0.5943(2) 0.0436(9) Uani 1 1 d . . . . .
H4 H 0.873863 0.541014 0.619135 0.052 Uiso 1 1 calc R U . . .
C5 C 1.0003(3) 0.4304(4) 0.6016(2) 0.0384(8) Uani 1 1 d . . . . .
C6 C 0.9219(4) -0.5418(4) 0.3528(2) 0.0450(9) Uani 1 1 d . . . . .
H6 H 0.945455 -0.624255 0.328553 0.054 Uiso 1 1 calc R U . . .
C7 C 0.8129(4) -0.5333(4) 0.3429(2) 0.0454(9) Uani 1 1 d . . . . .
C8 C 0.7299(4) -0.6535(5) 0.2922(3) 0.0664(13) Uani 1 1 d . . . . .
H8A H 0.657972 -0.628413 0.292306 0.100 Uiso 1 1 calc R U . . .
H8B H 0.726538 -0.657550 0.232298 0.100 Uiso 1 1 calc R U . . .
H8C H 0.752649 -0.750725 0.319878 0.100 Uiso 1 1 calc R U . . .
C9 C 0.7792(3) -0.4089(4) 0.3809(2) 0.0416(8) Uani 1 1 d . . . . .
H9 H 0.704853 -0.400667 0.373439 0.050 Uiso 1 1 calc R U . . .
C10 C 0.8530(3) -0.2974(4) 0.4293(2) 0.0358(7) Uani 1 1 d . . . . .
C11 C 1.0356(3) 0.3076(4) 0.5625(2) 0.0347(7) Uani 1 1 d . . . . .
C12 C 0.8126(3) -0.1762(4) 0.4762(3) 0.0440(8) Uani 1 1 d . . . . .
H12A H 0.732419 -0.181917 0.456400 0.053 Uiso 1 1 calc R U . . .
H12B H 0.843062 -0.196083 0.539341 0.053 Uiso 1 1 calc R U . . .
C13 C 0.6009(3) 0.0562(5) 0.3791(3) 0.0497(9) Uani 1 1 d . . . . .
H13 H 0.648351 0.013490 0.354473 0.060 Uiso 1 1 calc R U . . .
C14 C 0.4886(4) 0.0349(7) 0.3371(3) 0.0663(12) Uani 1 1 d . . . . .
H14 H 0.460988 -0.024353 0.286188 0.080 Uiso 1 1 calc R U . . .
C15 C 0.4169(4) 0.1029(7) 0.3714(4) 0.0723(14) Uani 1 1 d . . . . .
H15 H 0.340434 0.093247 0.342985 0.087 Uiso 1 1 calc R U . . .
C16 C 0.4611(4) 0.1835(6) 0.4472(4) 0.0645(13) Uani 1 1 d . . . . .
H16 H 0.414136 0.228586 0.471461 0.077 Uiso 1 1 calc R U . . .
N1 N 0.6447(3) 0.1361(4) 0.4543(2) 0.0441(7) Uani 1 1 d . . . . .
N2 N 0.8032(3) 0.3655(3) 0.5585(2) 0.0433(7) Uani 1 1 d . . . . .
O1 O 0.8434(2) -0.0261(3) 0.46043(16) 0.0380(5) Uani 1 1 d . . . . .
O2 O 1.0097(3) -0.0700(5) 0.6744(3) 0.0867(12) Uani 1 1 d . . . . .
O3 O 0.8473(4) 0.0535(5) 0.6585(3) 0.0964(13) Uani 1 1 d . . . . .
O4 O 0.8738(4) -0.1916(4) 0.7127(3) 0.0889(12) Uani 1 1 d . . . . .
O5 O 0.9790(4) 0.0045(5) 0.8016(3) 0.0944(13) Uani 1 1 d . . . . .
O8 O 0.9617(2) 0.2039(3) 0.51608(16) 0.0383(5) Uani 1 1 d . . . . .
Cl1 Cl 0.92646(9) -0.04945(13) 0.71444(7) 0.0571(3) Uani 1 1 d . . . . .
Cu1 Cu 0.80930(3) 0.16639(5) 0.50606(3) 0.03782(17) Uani 1 1 d . . . . .
Cu2 Cu 1.000000 0.000000 0.500000 0.03792(19) Uani 1 2 d S . P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.357(5) . ?
C1 C16 1.395(7) . ?
C1 C2 1.481(6) . ?
C2 C3 1.531(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N2 1.470(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N2 1.280(5) . ?
C4 C5 1.436(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.404(5) 3_756 ?
C5 C11 1.412(5) . ?
C6 C7 1.365(6) . ?
C6 H6 0.9300 . ?
C7 C9 1.404(5) . ?
C7 C8 1.515(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.391(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.405(5) 3_756 ?
C10 C12 1.513(5) . ?
C11 O8 1.335(4) . ?
C12 O1 1.429(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N1 1.340(5) . ?
C13 C14 1.373(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.386(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.351(8) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
N1 Cu1 2.001(3) . ?
N2 Cu1 1.962(3) . ?
O1 Cu2 1.903(2) . ?
O1 Cu1 1.964(2) . ?
O2 Cl1 1.466(4) . ?
O3 Cl1 1.417(4) . ?
O4 Cl1 1.419(4) . ?
O5 Cl1 1.408(4) . ?
O8 Cu2 1.904(2) . ?
O8 Cu1 1.952(2) . ?
Cu1 Cu2 2.9082(7) . ?

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 C16 119.7(4) . . ?
N1 C1 C2 117.6(4) . . ?
C16 C1 C2 122.7(4) . . ?
C1 C2 C3 112.1(4) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
N2 C3 C2 111.1(3) . . ?
N2 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
N2 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
N2 C4 C5 129.3(3) . . ?
N2 C4 H4 115.4 . . ?
C5 C4 H4 115.4 . . ?
C6 C5 C11 118.8(3) 3_756 . ?
C6 C5 C4 117.6(3) 3_756 . ?
C11 C5 C4 123.6(3) . . ?
C7 C6 C5 122.3(3) . 3_756 ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 3_756 . ?
C6 C7 C9 118.0(3) . . ?
C6 C7 C8 121.4(4) . . ?
C9 C7 C8 120.6(4) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C7 122.5(4) . . ?
C10 C9 H9 118.8 . . ?
C7 C9 H9 118.8 . . ?
C9 C10 C11 118.4(3) . 3_756 ?
C9 C10 C12 119.2(3) . . ?
C11 C10 C12 122.3(3) 3_756 . ?
O8 C11 C10 120.4(3) . 3_756 ?
O8 C11 C5 119.5(3) . . ?
C10 C11 C5 120.0(3) 3_756 . ?
O1 C12 C10 112.8(3) . . ?
O1 C12 H12A 109.0 . . ?
C10 C12 H12A 109.0 . . ?
O1 C12 H12B 109.0 . . ?
C10 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
N1 C13 C14 122.5(4) . . ?
N1 C13 H13 118.7 . . ?
C14 C13 H13 118.7 . . ?
C13 C14 C15 119.2(5) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C16 C15 C14 118.2(4) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
C15 C16 C1 121.4(4) . . ?
C15 C16 H16 119.3 . . ?
C1 C16 H16 119.3 . . ?
C13 N1 C1 118.9(4) . . ?
C13 N1 Cu1 118.6(2) . . ?
C1 N1 Cu1 122.4(3) . . ?
C4 N2 C3 116.1(3) . . ?
C4 N2 Cu1 124.1(3) . . ?
C3 N2 Cu1 119.8(3) . . ?
C12 O1 Cu2 112.7(2) . . ?
C12 O1 Cu1 127.6(2) . . ?
Cu2 O1 Cu1 97.52(10) . . ?
C11 O8 Cu2 123.5(2) . . ?
C11 O8 Cu1 130.9(2) . . ?
Cu2 O8 Cu1 97.91(11) . . ?
O5 Cl1 O3 113.3(3) . . ?
O5 Cl1 O4 111.5(3) . . ?
O3 Cl1 O4 108.7(3) . . ?
O5 Cl1 O2 109.2(2) . . ?
O3 Cl1 O2 105.8(3) . . ?
O4 Cl1 O2 108.1(3) . . ?
O8 Cu1 N2 90.93(12) . . ?
O8 Cu1 O1 79.22(10) . . ?
N2 Cu1 O1 169.94(12) . . ?
O8 Cu1 N1 161.40(12) . . ?
N2 Cu1 N1 95.32(13) . . ?
O1 Cu1 N1 94.69(12) . . ?
O8 Cu1 Cu2 40.43(7) . . ?
N2 Cu1 Cu2 129.49(10) . . ?
O1 Cu1 Cu2 40.45(7) . . ?
N1 Cu1 Cu2 135.02(9) . . ?
O1 Cu2 O1 180.0 . 3_756 ?
O1 Cu2 O8 98.06(10) . 3_756 ?
O1 Cu2 O8 81.94(10) 3_756 3_756 ?
O1 Cu2 O8 81.94(10) . . ?
O1 Cu2 O8 98.06(10) 3_756 . ?
O8 Cu2 O8 180.00(14) 3_756 . ?
O1 Cu2 Cu1 42.03(7) . . ?
O1 Cu2 Cu1 137.97(7) 3_756 . ?
O8 Cu2 Cu1 138.34(7) 3_756 . ?
O8 Cu2 Cu1 41.66(7) . . ?
O1 Cu2 Cu1 137.97(7) . 3_756 ?
O1 Cu2 Cu1 42.03(7) 3_756 3_756 ?
O8 Cu2 Cu1 41.66(7) 3_756 3_756 ?
O8 Cu2 Cu1 138.34(7) . 3_756 ?
Cu1 Cu2 Cu1 180.0 . 3_756 ?

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 58.2(5) . . . . ?
C16 C1 C2 C3 -120.4(4) . . . . ?
C1 C2 C3 N2 -74.7(5) . . . . ?
N2 C4 C5 C6 -178.0(4) . . . 3_756 ?
N2 C4 C5 C11 4.7(6) . . . . ?
C5 C6 C7 C9 -0.7(5) 3_756 . . . ?
C5 C6 C7 C8 179.0(4) 3_756 . . . ?
C6 C7 C9 C10 -1.4(5) . . . . ?
C8 C7 C9 C10 178.8(4) . . . . ?
C7 C9 C10 C11 2.4(5) . . . 3_756 ?
C7 C9 C10 C12 -173.6(3) . . . . ?
C6 C5 C11 O8 -177.4(3) 3_756 . . . ?
C4 C5 C11 O8 -0.2(5) . . . . ?
C6 C5 C11 C10 0.9(5) 3_756 . . 3_756 ?
C4 C5 C11 C10 178.1(3) . . . 3_756 ?
C9 C10 C12 O1 -132.1(3) . . . . ?
C11 C10 C12 O1 52.1(5) 3_756 . . . ?
N1 C13 C14 C15 2.4(7) . . . . ?
C13 C14 C15 C16 -2.3(8) . . . . ?
C14 C15 C16 C1 0.9(8) . . . . ?
N1 C1 C16 C15 0.6(7) . . . . ?
C2 C1 C16 C15 179.1(5) . . . . ?
C14 C13 N1 C1 -1.0(6) . . . . ?
C14 C13 N1 Cu1 -177.3(4) . . . . ?
C16 C1 N1 C13 -0.5(6) . . . . ?
C2 C1 N1 C13 -179.2(4) . . . . ?
C16 C1 N1 Cu1 175.7(3) . . . . ?
C2 C1 N1 Cu1 -3.0(5) . . . . ?
C5 C4 N2 C3 -179.1(4) . . . . ?
C5 C4 N2 Cu1 2.9(6) . . . . ?
C2 C3 N2 C4 -144.7(4) . . . . ?
C2 C3 N2 Cu1 33.4(5) . . . . ?
C10 C12 O1 Cu2 -60.4(4) . . . . ?
C10 C12 O1 Cu1 179.5(2) . . . . ?
C10 C11 O8 Cu2 27.3(4) 3_756 . . . ?
C5 C11 O8 Cu2 -154.4(2) . . . . ?
C10 C11 O8 Cu1 169.6(2) 3_756 . . . ?
C5 C11 O8 Cu1 -12.0(5) . . . . ?

_refine_diff_density_max         1.049
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.153

