# 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 1544808'
_audit_update_record             
;
2017-04-19 deposited with the CCDC.
2017-05-19 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            Cu(14-TMC)(NO3)2
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H32 Cu N6 O6'
_chemical_formula_iupac          ?
_chemical_formula_weight         443.99

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   7.9917(4)
_cell_length_b                   15.0923(8)
_cell_length_c                   8.3426(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.381(2)
_cell_angle_gamma                90
_cell_volume                     965.38(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9883
_cell_measurement_theta_min      2.8808
_cell_measurement_theta_max      28.1945
_cell_measurement_temperature    173.(2)

_exptl_crystal_description       CUBIC
_exptl_crystal_colour            'clear light purple'
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             470

_exptl_absorpt_coefficient_mu    1.175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/3 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.87

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173.(2)

_diffrn_source                   'Sealed tube'
_diffrn_source_type              'Sealed tube'

_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  TRIUMPH

_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '/f and /w scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            39083
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_full        28.34
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;
;

_reflns_number_total             2395
_reflns_number_gt                2060
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0977
_refine_ls_goodness_of_fit_ref   0.801
_refine_ls_restrained_S_all      0.801
_refine_ls_number_reflns         2395
_refine_ls_number_parameters     126
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.1247P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.494
_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 APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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 0.5 0 0.5 0.01243(11) Uani d . P S 1 . .
O O1 0.40194(18) 0.80690(8) 0.81760(17) 0.0317(3) Uani d . . . 1 . .
O O2 0.34613(17) 0.93939(8) 0.71539(16) 0.0293(3) Uani d . . . 1 . .
O O3 0.19108(16) 0.88327(9) 0.86470(16) 0.0300(3) Uani d . . . 1 . .
N N1 0.50304(16) 0.12564(8) 0.60399(16) 0.0143(3) Uani d . . . 1 . .
N N2 0.25429(16) 0.03071(9) 0.34583(16) 0.0145(3) Uani d . . . 1 . .
N N3 0.31265(17) 0.87600(9) 0.79904(16) 0.0177(3) Uani d . . . 1 . .
C C1 0.3307(2) -0.17446(10) 0.3847(2) 0.0178(3) Uani d . . . 1 . .
H H1A 0.3187 -0.1819 0.4988 0.021 Uiso calc U . R 1 . .
H H1B 0.3388 -0.2343 0.3389 0.021 Uiso calc U . R 1 . .
C C2 0.1673(2) -0.12927(10) 0.2769(2) 0.0207(3) Uani d . . . 1 . .
H H2A 0.1815 -0.1196 0.164 0.025 Uiso calc U . R 1 . .
H H2B 0.067 -0.1697 0.265 0.025 Uiso calc U . R 1 . .
C C3 0.12483(19) -0.04102(10) 0.3439(2) 0.0185(3) Uani d . . . 1 . .
H H3A 0.0088 -0.0212 0.2749 0.022 Uiso calc U . R 1 . .
H H3B 0.1173 -0.0499 0.4593 0.022 Uiso calc U . R 1 . .
C C4 0.2456(2) 0.05512(11) 0.17038(19) 0.0199(3) Uani d . . . 1 . .
H H4A 0.128 0.0761 0.1128 0.03 Uiso calc U . R 1 . .
H H4B 0.2731 0.0031 0.1122 0.03 Uiso calc U . R 1 . .
H H4C 0.3302 0.1022 0.1709 0.03 Uiso calc U . R 1 . .
C C5 0.2039(2) 0.11051(10) 0.4275(2) 0.0174(3) Uani d . . . 1 . .
H H5A 0.1676 0.0925 0.5268 0.021 Uiso calc U . R 1 . .
H H5B 0.1046 0.141 0.3487 0.021 Uiso calc U . R 1 . .
C C6 0.35858(19) 0.17227(10) 0.4791(2) 0.0175(3) Uani d . . . 1 . .
H H6A 0.3969 0.1892 0.3803 0.021 Uiso calc U . R 1 . .
H H6B 0.326 0.2268 0.5289 0.021 Uiso calc U . R 1 . .
C C7 0.4662(2) 0.13018(11) 0.76964(19) 0.0206(3) Uani d . . . 1 . .
H H7A 0.4564 0.1923 0.7999 0.031 Uiso calc U . R 1 . .
H H7B 0.5615 0.1019 0.8546 0.031 Uiso calc U . R 1 . .
H H7C 0.3566 0.0993 0.7631 0.031 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 N2 3_656 2.0737(13) ?
Cu1 N2 . 2.0738(13) ?
Cu1 N1 . 2.0825(12) ?
Cu1 N1 3_656 2.0825(12) ?
O1 N3 . 1.2484(18) ?
O2 N3 . 1.2567(17) ?
O3 N3 . 1.2474(18) ?
N1 C7 . 1.4935(19) ?
N1 C6 . 1.4951(19) ?
N1 C1 3_656 1.4987(18) ?
N2 C4 . 1.4918(19) ?
N2 C5 . 1.4937(19) ?
N2 C3 . 1.4945(19) ?
C1 N1 3_656 1.4987(18) ?
C1 C2 . 1.522(2) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C2 C3 . 1.520(2) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C4 H4C . 0.98 ?
C5 C6 . 1.510(2) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
C7 H7C . 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
N2 Cu1 N2 3_656 . 180.0 ?
N2 Cu1 N1 3_656 . 92.72(5) ?
N2 Cu1 N1 . . 87.28(5) ?
N2 Cu1 N1 3_656 3_656 87.28(5) ?
N2 Cu1 N1 . 3_656 92.72(5) ?
N1 Cu1 N1 . 3_656 180.00(3) ?
C7 N1 C6 . . 107.96(11) ?
C7 N1 C1 . 3_656 108.76(12) ?
C6 N1 C1 . 3_656 108.01(12) ?
C7 N1 Cu1 . . 116.43(9) ?
C6 N1 Cu1 . . 102.84(9) ?
C1 N1 Cu1 3_656 . 112.33(9) ?
C4 N2 C5 . . 107.74(12) ?
C4 N2 C3 . . 109.16(12) ?
C5 N2 C3 . . 108.30(11) ?
C4 N2 Cu1 . . 115.94(9) ?
C5 N2 Cu1 . . 103.12(9) ?
C3 N2 Cu1 . . 112.10(10) ?
O3 N3 O1 . . 120.51(13) ?
O3 N3 O2 . . 119.41(14) ?
O1 N3 O2 . . 120.07(13) ?
N1 C1 C2 3_656 . 114.49(12) ?
N1 C1 H1A 3_656 . 108.6 ?
C2 C1 H1A . . 108.6 ?
N1 C1 H1B 3_656 . 108.6 ?
C2 C1 H1B . . 108.6 ?
H1A C1 H1B . . 107.6 ?
C3 C2 C1 . . 114.75(13) ?
C3 C2 H2A . . 108.6 ?
C1 C2 H2A . . 108.6 ?
C3 C2 H2B . . 108.6 ?
C1 C2 H2B . . 108.6 ?
H2A C2 H2B . . 107.6 ?
N2 C3 C2 . . 114.39(13) ?
N2 C3 H3A . . 108.7 ?
C2 C3 H3A . . 108.7 ?
N2 C3 H3B . . 108.7 ?
C2 C3 H3B . . 108.7 ?
H3A C3 H3B . . 107.6 ?
N2 C4 H4A . . 109.5 ?
N2 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
N2 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
N2 C5 C6 . . 108.87(11) ?
N2 C5 H5A . . 109.9 ?
C6 C5 H5A . . 109.9 ?
N2 C5 H5B . . 109.9 ?
C6 C5 H5B . . 109.9 ?
H5A C5 H5B . . 108.3 ?
N1 C6 C5 . . 108.48(12) ?
N1 C6 H6A . . 110.0 ?
C5 C6 H6A . . 110.0 ?
N1 C6 H6B . . 110.0 ?
C5 C6 H6B . . 110.0 ?
H6A C6 H6B . . 108.4 ?
N1 C7 H7A . . 109.5 ?
N1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
N1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 3_656 . . . -65.58(18) ?
C4 N2 C3 C2 . . . . 67.67(16) ?
C5 N2 C3 C2 . . . . -175.30(13) ?
Cu1 N2 C3 C2 . . . . -62.19(15) ?
C1 C2 C3 N2 . . . . 66.45(18) ?
C4 N2 C5 C6 . . . . -79.54(14) ?
C3 N2 C5 C6 . . . . 162.51(13) ?
Cu1 N2 C5 C6 . . . . 43.57(13) ?
C7 N1 C6 C5 . . . . -79.48(14) ?
C1 N1 C6 C5 3_656 . . . 163.08(11) ?
Cu1 N1 C6 C5 . . . . 44.15(12) ?
N2 C5 C6 N1 . . . . -62.21(16) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C7 H7C O2 1_545 0.98 2.44 3.029(2) 117.9 ?
C7 H7B O3 3_667 0.98 2.61 3.484(2) 148.0 ?
C6 H6B O3 2_546 0.99 2.54 3.505(2) 165.2 ?
C6 H6A O1 3_666 0.99 2.61 3.544(2) 157.3 ?
C5 H5B O3 3_566 0.99 2.55 3.402(2) 143.9 ?
C4 H4C O2 3_666 0.98 2.57 3.131(2) 116.4 ?
C4 H4C O1 3_666 0.98 2.52 3.481(2) 166.3 ?
C3 H3B O2 1_545 0.99 2.39 3.119(2) 129.5 ?
C2 H2B O1 4_565 0.99 2.56 3.494(2) 157.5 ?
C2 H2A O3 1_544 0.99 2.52 3.502(2) 171.2 ?
C1 H1A N3 1_545 0.99 2.67 3.582(2) 154.0 ?
C1 H1A O2 1_545 0.99 2.54 3.223(2) 126.2 ?
C1 H1A O1 1_545 0.99 2.56 3.506(2) 160.1 ?
C7 H7C O2 1_545 0.98 2.44 3.029(2) 117.9 ?
C7 H7B O3 3_667 0.98 2.61 3.484(2) 148.0 ?
C6 H6B O3 2_546 0.99 2.54 3.505(2) 165.2 ?
C6 H6A O1 3_666 0.99 2.61 3.544(2) 157.3 ?
C5 H5B O3 3_566 0.99 2.55 3.402(2) 143.9 ?
C4 H4C O2 3_666 0.98 2.57 3.131(2) 116.4 ?
C4 H4C O1 3_666 0.98 2.52 3.481(2) 166.3 ?
C3 H3B O2 1_545 0.99 2.39 3.119(2) 129.5 ?
C2 H2B O1 4_565 0.99 2.56 3.494(2) 157.5 ?
C2 H2A O3 1_544 0.99 2.52 3.502(2) 171.2 ?
C1 H1A N3 1_545 0.99 2.67 3.582(2) 154.0 ?
C1 H1A O2 1_545 0.99 2.54 3.223(2) 126.2 ?
C1 H1A O1 1_545 0.99 2.56 3.506(2) 160.1 ?
C7 H7C O2 1_545 0.98 2.44 3.029(2) 117.9 ?
C7 H7B O3 3_667 0.98 2.61 3.484(2) 148.0 ?
C6 H6B O3 2_546 0.99 2.54 3.505(2) 165.2 ?
C6 H6A O1 3_666 0.99 2.61 3.544(2) 157.3 ?
C5 H5B O3 3_566 0.99 2.55 3.402(2) 143.9 ?
C4 H4C O2 3_666 0.98 2.57 3.131(2) 116.4 ?
C4 H4C O1 3_666 0.98 2.52 3.481(2) 166.3 ?
C3 H3B O2 1_545 0.99 2.39 3.119(2) 129.5 ?
C2 H2A O3 1_544 0.99 2.52 3.502(2) 171.2 ?
C2 H2B O1 4_565 0.99 2.56 3.494(2) 157.5 ?
C1 H1A N3 1_545 0.99 2.67 3.582(2) 154.0 ?
C1 H1A O2 1_545 0.99 2.54 3.223(2) 126.2 ?
C1 H1A O1 1_545 0.99 2.56 3.506(2) 160.1 ?
C1 H1A O1 1_545 0.99 2.56 3.506(2) 160.1 ?
C1 H1A O2 1_545 0.99 2.54 3.223(2) 126.2 ?
C1 H1A N3 1_545 0.99 2.67 3.582(2) 154.0 ?
C2 H2B O1 4_565 0.99 2.56 3.494(2) 157.5 ?
C2 H2A O3 1_544 0.99 2.52 3.502(2) 171.2 ?
C3 H3B O2 1_545 0.99 2.39 3.119(2) 129.5 ?
C4 H4C O1 3_666 0.98 2.52 3.481(2) 166.3 ?
C4 H4C O2 3_666 0.98 2.57 3.131(2) 116.4 ?
C5 H5B O3 3_566 0.99 2.55 3.402(2) 143.9 ?
C6 H6A O1 3_666 0.99 2.61 3.544(2) 157.3 ?
C6 H6B O3 2_546 0.99 2.54 3.505(2) 165.2 ?
C7 H7B O3 3_667 0.98 2.61 3.484(2) 148.0 ?
C7 H7C O2 1_545 0.98 2.44 3.029(2) 117.9 ?

