# 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 1559839'
_audit_update_record             
;
2017-09-17 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H21 Cu N5 O3'
_chemical_formula_weight         515.02

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'

_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                   14.291(2)
_cell_length_b                   13.296(2)
_cell_length_c                   12.436(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.673(4)
_cell_angle_gamma                90
_cell_volume                     2251.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9976
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      25.83

_exptl_crystal_description       block
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_F_000             1060
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.010
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            73649
_diffrn_reflns_av_unetI/netI     0.1808
_diffrn_reflns_av_R_equivalents  0.2006
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.992
_diffrn_reflns_theta_max         29.803
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5862
_reflns_number_gt                2994
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0535P)²+16.5152P] 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         5862
_refine_ls_number_parameters     320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2352
_refine_ls_R_factor_gt           0.1021
_refine_ls_wR_factor_ref         0.2245
_refine_ls_wR_factor_gt          0.1819
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.5529(5) 0.0011(5) 0.7804(5) 0.0360(16) Uani 1 1 d . . . . .
C2 C 0.5826(5) -0.0521(5) 0.6990(5) 0.0364(15) Uani 1 1 d . . . . .
H2 H 0.648603 -0.063784 0.707492 0.044 Uiso 1 1 calc R U . . .
C3 C 0.5109(5) -0.0857(5) 0.6074(6) 0.0416(17) Uani 1 1 d . . . . .
H3 H 0.528742 -0.121393 0.552318 0.050 Uiso 1 1 calc R U . . .
C4 C 0.4125(6) -0.0689(6) 0.5926(6) 0.050(2) Uani 1 1 d . . . . .
H4 H 0.366633 -0.093476 0.527804 0.060 Uiso 1 1 calc R U . . .
C5 C 0.3799(5) -0.0183(5) 0.6686(6) 0.0425(17) Uani 1 1 d . . . . .
H5 H 0.313336 -0.007948 0.658007 0.051 Uiso 1 1 calc R U . . .
C6 C 0.4500(5) 0.0166(4) 0.7615(5) 0.0293(14) Uani 1 1 d . . . . .
C7 C 0.5383(4) 0.0851(4) 0.9214(5) 0.0220(12) Uani 1 1 d . . . . .
C8 C 0.5710(5) 0.1419(5) 1.0300(5) 0.0326(15) Uani 1 1 d . . . . .
C9 C 0.5070(4) 0.1900(5) 1.0723(5) 0.0299(14) Uani 1 1 d . . . . .
H9 H 0.439687 0.185534 1.036806 0.036 Uiso 1 1 calc R U . . .
C10 C 0.5451(5) 0.2486(5) 1.1740(6) 0.0452(18) Uani 1 1 d . . . . .
H10 H 0.503159 0.282717 1.205727 0.054 Uiso 1 1 calc R U . . .
C11 C 0.6455(5) 0.2524(5) 1.2226(6) 0.0375(16) Uani 1 1 d . . . . .
H11 H 0.674076 0.290559 1.286818 0.045 Uiso 1 1 calc R U . . .
C12 C 0.7014(5) 0.1970(5) 1.1716(5) 0.0369(16) Uani 1 1 d . . . . .
H12 H 0.769192 0.199847 1.203679 0.044 Uiso 1 1 calc R U . . .
C13 C 0.7569(4) -0.1541(5) 1.0494(6) 0.0337(15) Uani 1 1 d . . . . .
C14 C 0.7408(4) -0.2516(5) 1.0819(6) 0.0360(16) Uani 1 1 d . . . . .
H14 H 0.709339 -0.260655 1.136630 0.043 Uiso 1 1 calc R U . . .
C15 C 0.7704(5) -0.3340(5) 1.0348(6) 0.0410(17) Uani 1 1 d . . . . .
H15 H 0.758844 -0.398016 1.058062 0.049 Uiso 1 1 calc R U . . .
C16 C 0.8175(5) -0.3233(5) 0.9525(7) 0.0484(19) Uani 1 1 d . . . . .
H16 H 0.835312 -0.379451 0.918611 0.058 Uiso 1 1 calc R U . . .
C17 C 0.8373(5) -0.2269(5) 0.9222(6) 0.0428(18) Uani 1 1 d . . . . .
H17 H 0.870209 -0.218700 0.868673 0.051 Uiso 1 1 calc R U . . .
C18 C 0.8093(4) -0.1437(5) 0.9697(5) 0.0297(14) Uani 1 1 d . . . . .
C19 C 0.8893(4) -0.0159(4) 0.8968(5) 0.0257(13) Uani 1 1 d . . . . .
C20 C 0.9129(4) 0.0864(4) 0.8768(5) 0.0250(13) Uani 1 1 d . . . . .
C21 C 0.9762(4) 0.1045(4) 0.8100(5) 0.0265(13) Uani 1 1 d . . . . .
C22 C 0.9998(5) 0.2029(5) 0.7950(6) 0.0329(15) Uani 1 1 d . . . . .
H22 H 1.039107 0.215088 0.748954 0.039 Uiso 1 1 calc R U . . .
C23 C 0.9122(4) 0.2674(4) 0.9071(5) 0.0287(14) Uani 1 1 d . . . . .
C24 C 0.8791(4) 0.1701(4) 0.9253(5) 0.0252(13) Uani 1 1 d . . . . .
C25 C 0.8821(5) 0.3568(5) 0.9621(6) 0.0421(17) Uani 1 1 d . . . . .
H25A H 0.840968 0.335294 1.006031 0.063 Uiso 1 1 calc R U . . .
H25B H 0.939551 0.389312 1.010359 0.063 Uiso 1 1 calc R U . . .
H25C H 0.846562 0.403164 0.905081 0.063 Uiso 1 1 calc R U . . .
C26 C 1.0186(4) 0.0211(5) 0.7583(6) 0.0337(15) Uani 1 1 d . . . . .
H26A H 1.061479 0.048889 0.718466 0.040 Uiso 1 1 calc R U . . .
H26B H 1.057262 -0.023223 0.817025 0.040 Uiso 1 1 calc R U . . .
N1 N 0.6047(4) 0.0449(4) 0.8786(4) 0.0358(13) Uani 1 1 d . . . . .
N2 N 0.4454(4) 0.0703(4) 0.8560(4) 0.0343(13) Uani 1 1 d . . . . .
H2A H 0.393010 0.090290 0.869811 0.041 Uiso 1 1 calc R U . . .
N3 N 0.6670(4) 0.1397(4) 1.0802(5) 0.0386(13) Uani 1 1 d . . . . .
N4 N 0.8272(3) -0.0415(4) 0.9483(4) 0.0285(11) Uani 1 1 d . . . . .
N5 N 0.9696(4) 0.2825(4) 0.8425(5) 0.0356(13) Uani 1 1 d . . . . .
O1 O 0.7248(3) -0.0728(3) 1.0900(4) 0.0378(11) Uani 1 1 d . . . . .
O2 O 0.8189(3) 0.1654(3) 0.9861(4) 0.0364(11) Uani 1 1 d . . . . .
O3 O 0.9428(3) -0.0332(3) 0.6832(4) 0.0467(12) Uani 1 1 d . . . . .
H3A H 0.966195 -0.078783 0.655082 0.070 Uiso 1 1 calc R U . . .
Cu1 Cu 0.75052(6) 0.04903(6) 1.01138(7) 0.0350(3) Uani 1 1 d . . . . .
H19 H 0.916(4) -0.068(4) 0.859(4) 0.016(14) 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
C1 N1 1.353(8) . ?
C1 C2 1.401(9) . ?
C1 C6 1.431(9) . ?
C2 C3 1.356(9) . ?
C3 C4 1.381(10) . ?
C4 C5 1.353(10) . ?
C5 C6 1.361(9) . ?
C6 N2 1.393(8) . ?
C7 N1 1.333(7) . ?
C7 N2 1.344(7) . ?
C7 C8 1.492(9) . ?
C8 N3 1.324(8) . ?
C8 C9 1.347(8) . ?
C9 C10 1.443(10) . ?
C10 C11 1.379(10) . ?
C11 C12 1.374(9) . ?
C12 N3 1.332(8) . ?
C13 O1 1.333(8) . ?
C13 C14 1.397(9) . ?
C13 C18 1.419(9) . ?
C14 C15 1.368(9) . ?
C15 C16 1.393(10) . ?
C16 C17 1.389(9) . ?
C17 C18 1.370(9) . ?
C18 N4 1.422(8) . ?
C19 N4 1.289(7) . ?
C19 C20 1.441(8) . ?
C20 C24 1.418(8) . ?
C20 C21 1.421(8) . ?
C21 C22 1.378(8) . ?
C21 C26 1.500(8) . ?
C22 N5 1.346(8) . ?
C23 N5 1.326(8) . ?
C23 C24 1.419(8) . ?
C23 C25 1.497(9) . ?
C24 O2 1.309(7) . ?
C26 O3 1.397(7) . ?
N1 Cu1 2.233(5) . ?
N3 Cu1 2.057(6) . ?
N4 Cu1 1.946(5) . ?
O1 Cu1 1.983(4) . ?
O2 Cu1 1.906(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
N1 C1 C2 131.8(7) . . ?
N1 C1 C6 109.8(6) . . ?
C2 C1 C6 118.4(6) . . ?
C3 C2 C1 117.1(6) . . ?
C2 C3 C4 122.5(7) . . ?
C5 C4 C3 122.7(7) . . ?
C4 C5 C6 116.2(7) . . ?
C5 C6 N2 132.8(6) . . ?
C5 C6 C1 123.0(6) . . ?
N2 C6 C1 104.2(5) . . ?
N1 C7 N2 113.0(5) . . ?
N1 C7 C8 120.0(5) . . ?
N2 C7 C8 127.0(5) . . ?
N3 C8 C9 123.7(6) . . ?
N3 C8 C7 114.2(5) . . ?
C9 C8 C7 122.0(6) . . ?
C8 C9 C10 118.5(6) . . ?
C11 C10 C9 118.0(6) . . ?
C12 C11 C10 116.8(6) . . ?
N3 C12 C11 125.8(6) . . ?
O1 C13 C14 122.5(6) . . ?
O1 C13 C18 120.0(5) . . ?
C14 C13 C18 117.5(6) . . ?
C15 C14 C13 121.2(6) . . ?
C14 C15 C16 121.0(6) . . ?
C17 C16 C15 118.5(7) . . ?
C18 C17 C16 121.2(7) . . ?
C17 C18 C13 120.5(6) . . ?
C17 C18 N4 126.7(6) . . ?
C13 C18 N4 112.7(5) . . ?
N4 C19 C20 124.6(6) . . ?
C24 C20 C21 118.4(5) . . ?
C24 C20 C19 122.6(5) . . ?
C21 C20 C19 118.9(5) . . ?
C22 C21 C20 117.7(5) . . ?
C22 C21 C26 119.7(5) . . ?
C20 C21 C26 122.5(5) . . ?
N5 C22 C21 124.2(6) . . ?
N5 C23 C24 122.1(6) . . ?
N5 C23 C25 118.2(5) . . ?
C24 C23 C25 119.7(5) . . ?
O2 C24 C20 125.2(5) . . ?
O2 C24 C23 116.4(5) . . ?
C20 C24 C23 118.3(5) . . ?
O3 C26 C21 109.6(5) . . ?
C7 N1 C1 105.9(5) . . ?
C7 N1 Cu1 108.2(4) . . ?
C1 N1 Cu1 144.1(5) . . ?
C7 N2 C6 107.1(5) . . ?
C8 N3 C12 116.8(6) . . ?
C8 N3 Cu1 117.8(4) . . ?
C12 N3 Cu1 125.4(5) . . ?
C19 N4 C18 122.4(5) . . ?
C19 N4 Cu1 126.4(4) . . ?
C18 N4 Cu1 111.1(4) . . ?
C23 N5 C22 119.1(5) . . ?
C13 O1 Cu1 109.9(4) . . ?
C24 O2 Cu1 126.5(4) . . ?
O2 Cu1 N4 93.22(19) . . ?
O2 Cu1 O1 157.7(2) . . ?
N4 Cu1 O1 84.52(19) . . ?
O2 Cu1 N3 89.1(2) . . ?
N4 Cu1 N3 177.7(2) . . ?
O1 Cu1 N3 93.2(2) . . ?
O2 Cu1 N1 107.9(2) . . ?
N4 Cu1 N1 101.6(2) . . ?
O1 Cu1 N1 94.2(2) . . ?
N3 Cu1 N1 78.0(2) . . ?

_refine_diff_density_max         2.063
_refine_diff_density_min         -1.130
_refine_diff_density_rms         0.113

