# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1547879'
_audit_update_record             
;
2017-05-04 deposited with the CCDC.
2017-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H32 Cu N6 O12'
_chemical_formula_weight         708.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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                   7.63550(10)
_cell_length_b                   19.7062(4)
_cell_length_c                   10.2494(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.4360(10)
_cell_angle_gamma                90
_cell_volume                     1516.68(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    10645
_cell_measurement_theta_min      6.69
_cell_measurement_theta_max      71.72

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_F_000             734
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    1.674
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrystalClear, Rigaku MSC, 2005'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IPDS'
_diffrn_measurement_method       'θ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13760
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         7.052
_diffrn_reflns_theta_max         66.972
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             2653
_reflns_number_gt                2338
_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       'CrystalClear, Rigaku MSC, 2005'
_computing_cell_refinement       'CrystalClear, Rigaku MSC, 2005'
_computing_data_reduction        'CrystalClear, Rigaku MSC, 2005'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond ver.3.1'
_computing_publication_material  'publCIF J.Appl.Cryst. 2010, 43, 920'
_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)+(0.0455P)²+0.7495P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2653
_refine_ls_number_parameters     278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0868
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.5000 0.0000 1.0000 0.01786(13) Uani 1 2 d S . P . .
O1 O 0.46239(17) 0.11670(7) 1.03608(13) 0.0197(3) Uani 1 1 d . . . . .
N1 N 0.6204(2) 0.01561(8) 1.18917(15) 0.0188(3) Uani 1 1 d . . . . .
N2 N 0.70859(19) 0.04570(8) 0.94390(15) 0.0188(3) Uani 1 1 d . . . . .
C1 C 0.6441(3) -0.03172(11) 1.2843(2) 0.0246(4) Uani 1 1 d . . . . .
C2 C 0.7303(3) -0.01849(11) 1.4119(2) 0.0287(5) Uani 1 1 d . . . . .
C3 C 0.7975(3) 0.04571(11) 1.4409(2) 0.0294(5) Uani 1 1 d . . . . .
C4 C 0.7751(3) 0.09524(11) 1.34273(19) 0.0247(4) Uani 1 1 d . . . . .
C5 C 0.6839(2) 0.07898(9) 1.21795(17) 0.0179(4) Uani 1 1 d . . . . .
C6 C 0.6431(2) 0.12860(9) 1.10045(17) 0.0171(4) Uani 1 1 d . . . . .
C7 C 0.7576(2) 0.10608(9) 1.00041(17) 0.0188(4) Uani 1 1 d . . . . .
C8 C 0.9028(3) 0.14071(11) 0.9719(2) 0.0252(4) Uani 1 1 d . . . . .
C9 C 0.9999(3) 0.11271(11) 0.8832(2) 0.0303(5) Uani 1 1 d . . . . .
C10 C 0.9487(3) 0.05106(11) 0.8260(2) 0.0280(5) Uani 1 1 d . . . . .
C11 C 0.8021(3) 0.01869(11) 0.85732(19) 0.0234(4) Uani 1 1 d . . . . .
C12 C 0.6699(3) 0.20176(9) 1.14682(19) 0.0215(4) Uani 1 1 d . . . . .
C13 C 0.6039(3) 0.25489(10) 1.0430(2) 0.0255(4) Uani 1 1 d . . . . .
C14 C 0.5687(4) 0.32288(12) 1.0976(3) 0.0384(6) Uani 1 1 d . . . . .
O2 O 0.5807(2) 0.24343(8) 0.92537(14) 0.0391(4) Uani 1 1 d . . . . .
N3 N 0.2137(2) 0.17610(9) 1.27025(17) 0.0306(4) Uani 1 1 d . . . . .
O3 O 0.2670(3) 0.12122(8) 1.31952(16) 0.0486(5) Uani 1 1 d . . . . .
O4 O 0.1186(2) 0.21466(9) 1.32416(18) 0.0491(5) Uani 1 1 d . . . . .
O5 O 0.25392(19) 0.19439(8) 1.16118(15) 0.0338(4) Uani 1 1 d . . . . .
O1W O 0.0519(3) 0.32392(11) 1.0881(2) 0.0589(6) Uani 1 1 d . . . . .
H1O H 0.400(3) 0.1350(12) 1.076(2) 0.035(7) Uiso 1 1 d . . . . .
H1 H 0.601(3) -0.0740(11) 1.261(2) 0.028(6) Uiso 1 1 d . . . . .
H2 H 0.745(3) -0.0505(11) 1.474(2) 0.028(6) Uiso 1 1 d . . . . .
H3 H 0.858(3) 0.0582(10) 1.523(2) 0.028(6) Uiso 1 1 d . . . . .
H4 H 0.821(3) 0.1386(12) 1.362(2) 0.032(6) Uiso 1 1 d . . . . .
H8 H 0.932(3) 0.1826(11) 1.009(2) 0.023(5) Uiso 1 1 d . . . . .
H9 H 1.102(3) 0.1353(12) 0.863(2) 0.043(7) Uiso 1 1 d . . . . .
H10 H 1.007(3) 0.0323(12) 0.764(2) 0.037(6) Uiso 1 1 d . . . . .
H11 H 0.765(3) -0.0237(12) 0.826(2) 0.024(5) Uiso 1 1 d . . . . .
H12A H 0.796(3) 0.2095(11) 1.180(2) 0.028(6) Uiso 1 1 d . . . . .
H12B H 0.604(3) 0.2057(10) 1.218(2) 0.026(5) Uiso 1 1 d . . . . .
H14A H 0.528(4) 0.3558(16) 1.026(3) 0.056(8) Uiso 1 1 d . . . . .
H14B H 0.675(4) 0.3386(14) 1.155(3) 0.057(8) Uiso 1 1 d . . . . .
H14C H 0.490(4) 0.3173(15) 1.154(3) 0.062(9) Uiso 1 1 d . . . . .
H1WA H 0.103(4) 0.2931(17) 1.138(3) 0.063(10) Uiso 1 1 d . . . . .
H1WB H 0.096(5) 0.3151(18) 1.020(4) 0.085(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
Cu N2 2.0026(14) . ?
Cu N2 2.0026(14) 3_657 ?
Cu N1 2.0132(16) 3_657 ?
Cu N1 2.0132(16) . ?
Cu O1 2.3549(13) 3_657 ?
Cu O1 2.3550(13) . ?
O1 C6 1.437(2) . ?
O1 H1O 0.77(3) . ?
N1 C1 1.338(2) . ?
N1 C5 1.353(2) . ?
N2 C11 1.346(2) . ?
N2 C7 1.346(2) . ?
C1 C2 1.378(3) . ?
C1 H1 0.91(2) . ?
C2 C3 1.377(3) . ?
C2 H2 0.89(2) . ?
C3 C4 1.390(3) . ?
C3 H3 0.92(2) . ?
C4 C5 1.379(3) . ?
C4 H4 0.93(2) . ?
C5 C6 1.539(2) . ?
C6 C12 1.520(2) . ?
C6 C7 1.529(2) . ?
C7 C8 1.377(3) . ?
C8 C9 1.387(3) . ?
C8 H8 0.92(2) . ?
C9 C10 1.375(3) . ?
C9 H9 0.95(3) . ?
C10 C11 1.375(3) . ?
C10 H10 0.92(2) . ?
C11 H11 0.92(2) . ?
C12 C13 1.512(3) . ?
C12 H12A 0.98(2) . ?
C12 H12B 0.97(2) . ?
C13 O2 1.208(2) . ?
C13 C14 1.495(3) . ?
C14 H14A 0.98(3) . ?
C14 H14B 0.97(3) . ?
C14 H14C 0.91(3) . ?
N3 O3 1.231(2) . ?
N3 O4 1.247(2) . ?
N3 O5 1.264(2) . ?
O1W H1WA 0.84(3) . ?
O1W H1WB 0.85(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
N2 Cu N2 180.0 . 3_657 ?
N2 Cu N1 92.31(6) . 3_657 ?
N2 Cu N1 87.69(6) 3_657 3_657 ?
N2 Cu N1 87.69(6) . . ?
N2 Cu N1 92.31(6) 3_657 . ?
N1 Cu N1 180.00(8) 3_657 . ?
N2 Cu O1 105.55(5) . 3_657 ?
N2 Cu O1 74.45(5) 3_657 3_657 ?
N1 Cu O1 75.34(5) 3_657 3_657 ?
N1 Cu O1 104.66(5) . 3_657 ?
N2 Cu O1 74.45(5) . . ?
N2 Cu O1 105.56(5) 3_657 . ?
N1 Cu O1 104.66(5) 3_657 . ?
N1 Cu O1 75.34(5) . . ?
O1 Cu O1 180.0 3_657 . ?
C6 O1 Cu 95.58(9) . . ?
C6 O1 H1O 108.1(18) . . ?
Cu O1 H1O 130.1(18) . . ?
C1 N1 C5 119.26(17) . . ?
C1 N1 Cu 124.99(14) . . ?
C5 N1 Cu 115.73(12) . . ?
C11 N2 C7 119.60(16) . . ?
C11 N2 Cu 123.79(13) . . ?
C7 N2 Cu 116.59(11) . . ?
N1 C1 C2 122.6(2) . . ?
N1 C1 H1 116.8(14) . . ?
C2 C1 H1 120.6(14) . . ?
C3 C2 C1 118.28(19) . . ?
C3 C2 H2 120.5(15) . . ?
C1 C2 H2 121.2(15) . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 123.4(13) . . ?
C4 C3 H3 116.8(13) . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 H4 121.4(14) . . ?
C3 C4 H4 119.7(14) . . ?
N1 C5 C4 121.18(17) . . ?
N1 C5 C6 113.73(15) . . ?
C4 C5 C6 125.09(17) . . ?
O1 C6 C12 111.22(15) . . ?
O1 C6 C7 105.24(13) . . ?
C12 C6 C7 115.10(15) . . ?
O1 C6 C5 107.27(14) . . ?
C12 C6 C5 111.19(14) . . ?
C7 C6 C5 106.33(14) . . ?
N2 C7 C8 121.23(17) . . ?
N2 C7 C6 113.39(15) . . ?
C8 C7 C6 125.32(17) . . ?
C7 C8 C9 119.21(19) . . ?
C7 C8 H8 120.2(13) . . ?
C9 C8 H8 120.6(13) . . ?
C10 C9 C8 119.10(18) . . ?
C10 C9 H9 120.1(15) . . ?
C8 C9 H9 120.8(15) . . ?
C9 C10 C11 119.41(19) . . ?
C9 C10 H10 121.0(15) . . ?
C11 C10 H10 119.5(15) . . ?
N2 C11 C10 121.45(19) . . ?
N2 C11 H11 114.7(13) . . ?
C10 C11 H11 123.7(13) . . ?
C13 C12 C6 115.33(16) . . ?
C13 C12 H12A 108.8(13) . . ?
C6 C12 H12A 109.1(13) . . ?
C13 C12 H12B 108.8(13) . . ?
C6 C12 H12B 104.8(13) . . ?
H12A C12 H12B 110.0(18) . . ?
O2 C13 C14 122.5(2) . . ?
O2 C13 C12 122.87(18) . . ?
C14 C13 C12 114.63(18) . . ?
C13 C14 H14A 111.5(17) . . ?
C13 C14 H14B 109.1(17) . . ?
H14A C14 H14B 111(2) . . ?
C13 C14 H14C 108.2(19) . . ?
H14A C14 H14C 113(2) . . ?
H14B C14 H14C 103(2) . . ?
O3 N3 O4 121.96(18) . . ?
O3 N3 O5 119.85(17) . . ?
O4 N3 O5 118.19(18) . . ?
H1WA O1W H1WB 98(3) . . ?

_refine_diff_density_max         0.419
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.051

_shelxl_version_number           2014/6

