# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1561132'
_audit_update_record             
;
2017-07-10 deposited with the CCDC.
2017-08-31 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H36 Cu N4 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         412.03

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   15.357(18)
_cell_length_b                   10.037(11)
_cell_length_c                   15.475(18)
_cell_angle_alpha                90
_cell_angle_beta                 118.482(18)
_cell_angle_gamma                90
_cell_volume                     2097.(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1500
_cell_measurement_theta_min      2.5268
_cell_measurement_theta_max      25.4645
_cell_measurement_temperature    93

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             884

_exptl_absorpt_coefficient_mu    1.067
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      93

_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker Tourbo X-ray Source'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayered conforcal mirror'

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            10600
_diffrn_reflns_av_R_equivalents  0.1447
_diffrn_reflns_av_unetI/netI     0.1569
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       12

_refine_special_details          
;
;

_reflns_number_total             3699
_reflns_number_gt                2420
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1264
_refine_ls_R_factor_gt           0.0744
_refine_ls_wR_factor_gt          0.1703
_refine_ls_wR_factor_ref         0.1838
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_number_reflns         3699
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0692P)²+3.8301P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.089
_refine_diff_density_min         -1.002
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker SMART APEXII ULTRA'
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruker AXS)'
_computing_publication_material  'Generate Report (Bruekr AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.42399(6) 0.73296(6) 0.25845(5) 0.0161(2) Uani d . . . 1 . .
O O1 0.4489(3) 0.8632(3) 0.1790(3) 0.0214(10) Uani d . . . 1 . .
O O2 0.3997(3) 0.6109(3) 0.1468(3) 0.0238(11) Uani d . . . 1 . .
O O3 0.3941(4) 0.6157(4) -0.0005(3) 0.0281(12) Uani d . . . 1 . .
O O4 0.4230(4) 0.8927(4) 0.0253(3) 0.0304(12) Uani d . . . 1 . .
C C1 0.4267(5) 0.8240(5) 0.0923(5) 0.0242(16) Uani d . . . 1 . .
C C2 0.4059(5) 0.6712(6) 0.0761(4) 0.0210(15) Uani d . . . 1 . .
N N2 0.8169(4) 0.7774(5) 0.5934(4) 0.0249(13) Uani d . . . 1 . .
N N1 0.4998(4) 0.8441(4) 0.3817(4) 0.0219(13) Uani d . . . 1 . .
H H1A 0.5153 0.9234 0.3639 0.026 Uiso calc U . R 1 . .
H H1B 0.4588 0.8616 0.4075 0.026 Uiso calc U . R 1 . .
N N3 0.4127(4) 0.5804(4) 0.3350(4) 0.0243(13) Uani d . . . 1 . .
H H3A 0.4627 0.5225 0.3466 0.029 Uiso calc U . R 1 . .
H H3B 0.4236 0.6122 0.3944 0.029 Uiso calc U . R 1 . .
N N4 0.2513(4) 0.7989(5) 0.1933(4) 0.0221(13) Uani d . . . 1 . .
C C3 0.5937(5) 0.7836(5) 0.4612(5) 0.0246(16) Uani d . . . 1 . .
H H3C 0.5779 0.6989 0.4835 0.029 Uiso calc U . R 1 . .
H H3D 0.6234 0.8449 0.5181 0.029 Uiso calc U . R 1 . .
C C4 0.6674(5) 0.7572(6) 0.4248(5) 0.0266(15) Uani d . . . 1 . .
H H4A 0.6814 0.842 0.401 0.032 Uiso calc U . R 1 . .
H H4B 0.6371 0.6955 0.3681 0.032 Uiso calc U . R 1 . .
C C6 0.9062(5) 0.7065(6) 0.6634(5) 0.0322(18) Uani d . . . 1 . .
H H6A 0.9542 0.7058 0.6379 0.039 Uiso calc U . R 1 . .
H H6B 0.8884 0.6128 0.6678 0.039 Uiso calc U . R 1 . .
C C8 0.8359(5) 0.9164(6) 0.5767(6) 0.0312(18) Uani d . . . 1 . .
H H8A 0.8645 0.9637 0.6405 0.037 Uiso calc U . R 1 . .
H H8B 0.7714 0.9589 0.5331 0.037 Uiso calc U . R 1 . .
C C5 0.7655(5) 0.6976(6) 0.5021(5) 0.0309(17) Uani d . . . 1 . .
H H5A 0.7526 0.6075 0.5195 0.037 Uiso calc U . R 1 . .
H H5B 0.8101 0.6875 0.4729 0.037 Uiso calc U . R 1 . .
C C7 0.9555(7) 0.7655(8) 0.7650(6) 0.053(2) Uani d . . . 1 . .
H H7A 0.9799 0.8549 0.7627 0.079 Uiso calc U . R 1 . .
H H7B 1.0111 0.7089 0.8088 0.079 Uiso calc U . R 1 . .
H H7C 0.9075 0.7713 0.7897 0.079 Uiso calc U . R 1 . .
C C9 0.9050(6) 0.9378(8) 0.5315(6) 0.046(2) Uani d . . . 1 . .
H H9A 0.9706 0.9009 0.5756 0.069 Uiso calc U . R 1 . .
H H9B 0.911 1.0333 0.5225 0.069 Uiso calc U . R 1 . .
H H9C 0.8775 0.8927 0.4677 0.069 Uiso calc U . R 1 . .
C C15 0.2179(5) 0.8508(6) 0.0919(5) 0.0258(16) Uani d . . . 1 . .
H H15A 0.2286 0.7804 0.0531 0.031 Uiso calc U . R 1 . .
H H15B 0.2604 0.9273 0.0962 0.031 Uiso calc U . R 1 . .
C C13 0.2406(5) 0.8997(6) 0.2579(5) 0.0283(17) Uani d . . . 1 . .
H H13A 0.2713 0.8646 0.3258 0.034 Uiso calc U . R 1 . .
H H13B 0.1692 0.9135 0.2358 0.034 Uiso calc U . R 1 . .
C C14 0.2882(5) 1.0350(6) 0.2585(5) 0.0317(18) Uani d . . . 1 . .
H H14A 0.3577 1.0216 0.2754 0.048 Uiso calc U . R 1 . .
H H14B 0.2845 1.0937 0.3073 0.048 Uiso calc U . R 1 . .
H H14C 0.2527 1.076 0.1933 0.048 Uiso calc U . R 1 . .
C C10 0.3187(5) 0.5030(6) 0.2923(5) 0.0322(18) Uani d . . . 1 . .
H H10A 0.3249 0.4291 0.3372 0.039 Uiso calc U . R 1 . .
H H10B 0.3065 0.4639 0.2288 0.039 Uiso calc U . R 1 . .
C C12 0.1912(5) 0.6799(6) 0.1863(5) 0.038(2) Uani d . . . 1 . .
H H12A 0.1835 0.6259 0.1296 0.045 Uiso calc U . R 1 . .
H H12B 0.1244 0.7102 0.1721 0.045 Uiso calc U . R 1 . .
C C11 0.2316(6) 0.5905(6) 0.2762(6) 0.0362(19) Uani d . . . 1 . .
H H11A 0.252 0.6473 0.335 0.043 Uiso calc U . R 1 . .
H H11B 0.1773 0.5323 0.271 0.043 Uiso calc U . R 1 . .
C C16 0.1076(5) 0.8964(6) 0.0347(5) 0.0318(18) Uani d . . . 1 . .
H H16A 0.0641 0.8202 0.0257 0.048 Uiso calc U . R 1 . .
H H16B 0.0937 0.9316 -0.0297 0.048 Uiso calc U . R 1 . .
H H16C 0.0955 0.966 0.0722 0.048 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O1 . 1.953(4) ?
Cu1 N3 . 1.994(5) ?
Cu1 O2 . 2.003(4) ?
Cu1 N1 . 2.029(5) ?
Cu1 N4 . 2.436(6) ?
O1 C1 . 1.278(8) ?
O2 C2 . 1.292(8) ?
O3 C2 . 1.244(8) ?
O4 C1 . 1.224(8) ?
C1 C2 . 1.562(8) ?
N2 C6 . 1.465(8) ?
N2 C8 . 1.473(8) ?
N2 C5 . 1.482(8) ?
N1 C3 . 1.507(8) ?
N1 H1A . 0.91 ?
N1 H1B . 0.91 ?
N3 C10 . 1.488(9) ?
N3 H3A . 0.91 ?
N3 H3B . 0.91 ?
N4 C12 . 1.482(8) ?
N4 C13 . 1.486(8) ?
N4 C15 . 1.492(8) ?
C3 C4 . 1.509(10) ?
C3 H3C . 0.99 ?
C3 H3D . 0.99 ?
C4 C5 . 1.529(9) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C6 C7 . 1.503(10) ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C8 C9 . 1.540(12) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
C7 H7C . 0.98 ?
C9 H9A . 0.98 ?
C9 H9B . 0.98 ?
C9 H9C . 0.98 ?
C15 C16 . 1.560(10) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C13 C14 . 1.540(9) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?
C10 C11 . 1.517(10) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C12 C11 . 1.517(9) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cu1 N3 . . 170.6(2) ?
O1 Cu1 O2 . . 82.99(19) ?
N3 Cu1 O2 . . 90.5(2) ?
O1 Cu1 N1 . . 91.6(2) ?
N3 Cu1 N1 . . 92.1(2) ?
O2 Cu1 N1 . . 159.1(2) ?
O1 Cu1 N4 . . 93.37(19) ?
N3 Cu1 N4 . . 94.0(2) ?
O2 Cu1 N4 . . 95.22(18) ?
N1 Cu1 N4 . . 105.3(2) ?
C1 O1 Cu1 . . 114.9(4) ?
C2 O2 Cu1 . . 112.6(3) ?
O4 C1 O1 . . 126.6(5) ?
O4 C1 C2 . . 119.6(6) ?
O1 C1 C2 . . 113.7(5) ?
O3 C2 O2 . . 124.2(6) ?
O3 C2 C1 . . 121.2(6) ?
O2 C2 C1 . . 114.6(5) ?
C6 N2 C8 . . 113.3(5) ?
C6 N2 C5 . . 109.1(5) ?
C8 N2 C5 . . 113.9(5) ?
C3 N1 Cu1 . . 116.3(3) ?
C3 N1 H1A . . 108.2 ?
Cu1 N1 H1A . . 108.2 ?
C3 N1 H1B . . 108.2 ?
Cu1 N1 H1B . . 108.2 ?
H1A N1 H1B . . 107.4 ?
C10 N3 Cu1 . . 118.5(4) ?
C10 N3 H3A . . 107.7 ?
Cu1 N3 H3A . . 107.7 ?
C10 N3 H3B . . 107.7 ?
Cu1 N3 H3B . . 107.7 ?
H3A N3 H3B . . 107.1 ?
C12 N4 C13 . . 109.4(6) ?
C12 N4 C15 . . 108.4(5) ?
C13 N4 C15 . . 112.1(5) ?
C12 N4 Cu1 . . 109.2(4) ?
C13 N4 Cu1 . . 110.8(4) ?
C15 N4 Cu1 . . 106.9(4) ?
N1 C3 C4 . . 111.2(5) ?
N1 C3 H3C . . 109.4 ?
C4 C3 H3C . . 109.4 ?
N1 C3 H3D . . 109.4 ?
C4 C3 H3D . . 109.4 ?
H3C C3 H3D . . 108.0 ?
C3 C4 C5 . . 114.2(6) ?
C3 C4 H4A . . 108.7 ?
C5 C4 H4A . . 108.7 ?
C3 C4 H4B . . 108.7 ?
C5 C4 H4B . . 108.7 ?
H4A C4 H4B . . 107.6 ?
N2 C6 C7 . . 114.1(6) ?
N2 C6 H6A . . 108.7 ?
C7 C6 H6A . . 108.7 ?
N2 C6 H6B . . 108.7 ?
C7 C6 H6B . . 108.7 ?
H6A C6 H6B . . 107.6 ?
N2 C8 C9 . . 116.7(6) ?
N2 C8 H8A . . 108.1 ?
C9 C8 H8A . . 108.1 ?
N2 C8 H8B . . 108.1 ?
C9 C8 H8B . . 108.1 ?
H8A C8 H8B . . 107.3 ?
N2 C5 C4 . . 114.4(5) ?
N2 C5 H5A . . 108.7 ?
C4 C5 H5A . . 108.7 ?
N2 C5 H5B . . 108.7 ?
C4 C5 H5B . . 108.7 ?
H5A C5 H5B . . 107.6 ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
N4 C15 C16 . . 115.8(6) ?
N4 C15 H15A . . 108.3 ?
C16 C15 H15A . . 108.3 ?
N4 C15 H15B . . 108.3 ?
C16 C15 H15B . . 108.3 ?
H15A C15 H15B . . 107.4 ?
N4 C13 C14 . . 113.6(6) ?
N4 C13 H13A . . 108.8 ?
C14 C13 H13A . . 108.8 ?
N4 C13 H13B . . 108.8 ?
C14 C13 H13B . . 108.8 ?
H13A C13 H13B . . 107.7 ?
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 ?
N3 C10 C11 . . 111.3(5) ?
N3 C10 H10A . . 109.4 ?
C11 C10 H10A . . 109.4 ?
N3 C10 H10B . . 109.4 ?
C11 C10 H10B . . 109.4 ?
H10A C10 H10B . . 108.0 ?
N4 C12 C11 . . 116.2(5) ?
N4 C12 H12A . . 108.2 ?
C11 C12 H12A . . 108.2 ?
N4 C12 H12B . . 108.2 ?
C11 C12 H12B . . 108.2 ?
H12A C12 H12B . . 107.4 ?
C10 C11 C12 . . 115.9(7) ?
C10 C11 H11A . . 108.3 ?
C12 C11 H11A . . 108.3 ?
C10 C11 H11B . . 108.3 ?
C12 C11 H11B . . 108.3 ?
H11A C11 H11B . . 107.4 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?

