# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1568167'
_audit_update_record             
;
2017-08-10 deposited with the CCDC.
2018-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H21 Cu N4 O5, H O'
_chemical_formula_sum            'C29 H22 Cu N4 O6'
_chemical_formula_weight         586.05

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   13.2955(11)
_cell_length_b                   17.6522(15)
_cell_length_c                   15.7208(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.201(2)
_cell_angle_gamma                90.00
_cell_volume                     3642.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9958
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      28.10

_exptl_crystal_description       rod
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.069
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1204
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7669
_exptl_absorpt_correction_T_max  0.8726
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(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 ApexII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            45620
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         27.10
_reflns_number_total             8026
_reflns_number_gt                5710
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'ApexII (Bruker, 2011)'
_computing_cell_refinement       'ApexII (Bruker, 2011)'
_computing_data_reduction        'ApexII (Bruker, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_refine_special_details          
; 

 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0983P)²+0.7737P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7998
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1764
_refine_ls_wR_factor_gt          0.1690
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.136
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.50901(3) 0.774919(16) 0.60517(2) 0.03202(15) Uani 1 1 d . . .
O1W O 0.42487(19) 0.88477(12) 0.55469(17) 0.0545(6) Uani 1 1 d . . .
O1 O 0.60397(16) 0.83716(10) 0.68182(13) 0.0367(5) Uani 1 1 d . . .
O2 O 0.69231(19) 0.73686(10) 0.73763(13) 0.0408(6) Uani 1 1 d . . .
O3 O 0.90832(19) 0.77880(9) 1.02283(12) 0.0394(6) Uani 1 1 d . . .
O4 O 1.0031(2) 0.88344(11) 1.03775(13) 0.0590(8) Uani 1 1 d . . .
O5 O 0.8944(3) 0.7104(2) 0.7334(2) 0.0926(10) Uani 1 1 d . . .
H5 H 0.9071 0.6706 0.7117 0.111 Uiso 1 1 d R . .
N1 N 0.8938(2) 1.07064(12) 0.74225(14) 0.0353(6) Uani 1 1 d . . .
N2 N 1.2395(6) 1.0634(3) 0.4438(5) 0.152(4) Uani 1 1 d . . .
N3 N 0.4243(2) 0.75708(13) 0.70072(15) 0.0345(6) Uani 1 1 d . . .
N4 N 0.1034(2) 0.72677(13) 1.01625(16) 0.0377(6) Uani 1 1 d . . .
C1 C 0.8626(3) 0.87656(14) 0.92312(17) 0.0403(8) Uani 1 1 d . . .
C2 C 0.7993(3) 0.82974(14) 0.86808(16) 0.0372(8) Uani 1 1 d . . .
H2 H 0.7958 0.7773 0.8809 0.045 Uiso 1 1 calc R . .
C3 C 0.7410(3) 0.85850(14) 0.79451(17) 0.0352(7) Uani 1 1 d . . .
C4 C 0.7464(3) 0.93485(14) 0.77509(17) 0.0363(7) Uani 1 1 d . . .
H4 H 0.7061 0.9547 0.7247 0.044 Uiso 1 1 calc R . .
C5 C 0.8106(3) 0.98218(14) 0.82950(17) 0.0372(7) Uani 1 1 d . . .
C6 C 0.8673(3) 0.95357(14) 0.90291(17) 0.0429(9) Uani 1 1 d . . .
H6 H 0.9103 0.9863 0.9405 0.051 Uiso 1 1 calc R . .
C7 C 0.9306(3) 0.84568(15) 1.00058(17) 0.0459(9) Uani 1 1 d . . .
C8 C 0.6751(3) 0.80642(14) 0.73407(18) 0.0346(7) Uani 1 1 d . . .
C9 C 0.8205(3) 1.06408(14) 0.80420(18) 0.0395(8) Uani 1 1 d . . .
H9A H 0.7532 1.0838 0.7774 0.047 Uiso 1 1 calc R . .
H9B H 0.8448 1.0948 0.8562 0.047 Uiso 1 1 calc R . .
C10 C 0.8665(3) 1.10206(16) 0.66471(18) 0.0440(8) Uani 1 1 d . . .
H10 H 0.8002 1.1230 0.6498 0.053 Uiso 1 1 calc R . .
C11 C 0.9326(3) 1.10466(17) 0.6063(2) 0.0554(11) Uani 1 1 d . . .
H11 H 0.9118 1.1275 0.5516 0.067 Uiso 1 1 calc R . .
C12 C 1.0291(3) 1.07447(16) 0.6261(2) 0.0508(10) Uani 1 1 d . . .
C13 C 1.0562(3) 1.0437(2) 0.7080(3) 0.0626(11) Uani 1 1 d . . .
H13 H 1.1225 1.0235 0.7254 0.075 Uiso 1 1 calc R . .
C14 C 0.9867(3) 1.0429(2) 0.7633(2) 0.0552(10) Uani 1 1 d . . .
H14 H 1.0060 1.0216 0.8190 0.066 Uiso 1 1 calc R . .
C15 C 1.1015(4) 1.07225(18) 0.5629(3) 0.0690(13) Uani 1 1 d . . .
C16 C 1.0730(4) 1.0927(2) 0.4785(3) 0.0834(16) Uani 1 1 d . . .
H16 H 1.0064 1.1111 0.4579 0.100 Uiso 1 1 calc R . .
C17 C 1.1473(6) 1.0852(3) 0.4223(4) 0.103(2) Uani 1 1 d . . .
H17 H 1.1260 1.0977 0.3634 0.124 Uiso 1 1 calc R . .
C18 C 1.2632(7) 1.0453(3) 0.5238(8) 0.194(6) Uani 1 1 d . . .
H18 H 1.3308 1.0279 0.5416 0.233 Uiso 1 1 calc R . .
C19 C 1.2025(5) 1.0483(3) 0.5858(5) 0.133(3) Uani 1 1 d . . .
H19 H 1.2283 1.0343 0.6436 0.160 Uiso 1 1 calc R . .
C20 C 0.4332(3) 0.8008(2) 0.7698(2) 0.0702(14) Uani 1 1 d . . .
H20 H 0.4846 0.8387 0.7760 0.084 Uiso 1 1 calc R . .
C21 C 0.3737(3) 0.7953(2) 0.8332(2) 0.0593(11) Uani 1 1 d . . .
H21 H 0.3848 0.8282 0.8815 0.071 Uiso 1 1 calc R . .
C22 C 0.2982(2) 0.74205(16) 0.82622(17) 0.0332(7) Uani 1 1 d . . .
C23 C 0.2856(3) 0.6984(2) 0.75304(19) 0.0481(9) Uani 1 1 d . . .
H23 H 0.2325 0.6620 0.7437 0.058 Uiso 1 1 calc R . .
C24 C 0.3498(3) 0.70715(18) 0.69299(19) 0.0407(8) Uani 1 1 d . . .
H24 H 0.3397 0.6755 0.6435 0.049 Uiso 1 1 calc R . .
C25 C 0.2307(2) 0.73561(16) 0.89183(18) 0.0347(7) Uani 1 1 d . . .
C26 C 0.2638(3) 0.75666(18) 0.97619(18) 0.0383(7) Uani 1 1 d . . .
H26 H 0.3311 0.7751 0.9929 0.046 Uiso 1 1 calc R . .
C27 C 0.1993(3) 0.75097(18) 1.03607(18) 0.0387(8) Uani 1 1 d . . .
H27 H 0.2241 0.7648 1.0940 0.046 Uiso 1 1 calc R . .
C28 C 0.0701(3) 0.7072(2) 0.9345(2) 0.0548(10) Uani 1 1 d . . .
H28 H 0.0016 0.6906 0.9194 0.066 Uiso 1 1 calc R . .
C29 C 0.1307(3) 0.7101(2) 0.8710(2) 0.0527(10) Uani 1 1 d . . .
H29 H 0.1045 0.6948 0.8138 0.063 Uiso 1 1 calc R . .


_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
Cu1 O1 1.941(2) . ?
Cu1 O3 1.953(2) 4_575 ?
Cu1 N4 2.022(2) 4_675 ?
Cu1 N3 2.041(2) . ?
Cu1 O1W 2.315(2) . ?
O1 C8 1.271(4) . ?
O2 C8 1.248(3) . ?
O3 C7 1.280(3) . ?
O3 Cu1 1.953(2) 4_676 ?
O4 C7 1.239(4) . ?
O5 H5 0.8112 . ?
N1 C14 1.322(5) . ?
N1 C10 1.335(4) . ?
N1 C9 1.487(4) . ?
N2 C17 1.277(10) . ?
N2 C18 1.287(13) . ?
N3 C24 1.317(4) . ?
N3 C20 1.322(4) . ?
N4 C28 1.336(4) . ?
N4 C27 1.334(4) . ?
N4 Cu1 2.022(2) 4_576 ?
C1 C6 1.400(4) . ?
C1 C2 1.381(4) . ?
C1 C7 1.498(5) . ?
C2 C3 1.382(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(3) . ?
C3 C8 1.500(4) . ?
C4 C5 1.388(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.370(4) . ?
C5 C9 1.511(3) . ?
C6 H6 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.370(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(5) . ?
C12 C15 1.490(5) . ?
C13 C14 1.365(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.370(6) . ?
C15 C19 1.399(8) . ?
C16 C17 1.432(7) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.363(9) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.371(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.366(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.372(4) . ?
C22 C25 1.475(3) . ?
C23 C24 1.378(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C29 1.393(5) . ?
C25 C26 1.380(4) . ?
C26 C27 1.374(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.380(4) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?

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
O1 Cu1 O3 174.56(9) . 4_575 ?
O1 Cu1 N4 91.36(10) . 4_675 ?
O3 Cu1 N4 88.28(10) 4_575 4_675 ?
O1 Cu1 N3 90.65(9) . . ?
O3 Cu1 N3 90.70(9) 4_575 . ?
N4 Cu1 N3 169.38(10) 4_675 . ?
O1 Cu1 O1W 88.24(9) . . ?
O3 Cu1 O1W 86.39(9) 4_575 . ?
N4 Cu1 O1W 95.43(9) 4_675 . ?
N3 Cu1 O1W 95.06(10) . . ?
C8 O1 Cu1 120.17(16) . . ?
C7 O3 Cu1 117.7(2) . 4_676 ?
C14 N1 C10 119.2(3) . . ?
C14 N1 C9 119.4(2) . . ?
C10 N1 C9 121.3(3) . . ?
C17 N2 C18 114.0(5) . . ?
C24 N3 C20 115.7(2) . . ?
C24 N3 Cu1 122.07(17) . . ?
C20 N3 Cu1 121.8(2) . . ?
C28 N4 C27 117.7(2) . . ?
C28 N4 Cu1 121.0(2) . 4_576 ?
C27 N4 Cu1 121.27(19) . 4_576 ?
C6 C1 C2 118.9(3) . . ?
C6 C1 C7 119.7(3) . . ?
C2 C1 C7 121.3(2) . . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 C8 119.9(2) . . ?
C4 C3 C8 120.1(3) . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C6 C5 C4 119.9(2) . . ?
C6 C5 C9 121.0(3) . . ?
C4 C5 C9 119.0(3) . . ?
C5 C6 C1 120.7(3) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
O4 C7 O3 124.3(3) . . ?
O4 C7 C1 120.7(2) . . ?
O3 C7 C1 115.0(3) . . ?
O2 C8 O1 124.1(3) . . ?
O2 C8 C3 119.4(3) . . ?
O1 C8 C3 116.5(2) . . ?
N1 C9 C5 109.9(2) . . ?
N1 C9 H9A 109.7 . . ?
C5 C9 H9A 109.7 . . ?
N1 C9 H9B 109.7 . . ?
C5 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
N1 C10 C11 121.1(3) . . ?
N1 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C12 120.6(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 117.0(3) . . ?
C13 C12 C15 120.5(4) . . ?
C11 C12 C15 122.5(3) . . ?
C12 C13 C14 119.5(4) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
N1 C14 C13 122.6(3) . . ?
N1 C14 H14 118.7 . . ?
C13 C14 H14 118.7 . . ?
C16 C15 C19 115.8(4) . . ?
C16 C15 C12 122.1(5) . . ?
C19 C15 C12 122.2(4) . . ?
C15 C16 C17 117.5(6) . . ?
C15 C16 H16 121.2 . . ?
C17 C16 H16 121.2 . . ?
N2 C17 C16 126.3(6) . . ?
N2 C17 H17 116.8 . . ?
C16 C17 H17 116.8 . . ?
N2 C18 C19 127.6(9) . . ?
N2 C18 H18 116.2 . . ?
C19 C18 H18 116.2 . . ?
C18 C19 C15 118.7(7) . . ?
C18 C19 H19 120.6 . . ?
C15 C19 H19 120.6 . . ?
N3 C20 C21 124.7(3) . . ?
N3 C20 H20 117.7 . . ?
C21 C20 H20 117.7 . . ?
C22 C21 C20 119.5(3) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 116.2(2) . . ?
C21 C22 C25 121.2(2) . . ?
C23 C22 C25 122.5(3) . . ?
C24 C23 C22 120.4(3) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
N3 C24 C23 123.4(2) . . ?
N3 C24 H24 118.3 . . ?
C23 C24 H24 118.3 . . ?
C29 C25 C26 117.3(2) . . ?
C29 C25 C22 121.7(3) . . ?
C26 C25 C22 121.0(3) . . ?
C27 C26 C25 120.1(3) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
N4 C27 C26 122.8(3) . . ?
N4 C27 H27 118.6 . . ?
C26 C27 H27 118.6 . . ?
N4 C28 C29 123.0(3) . . ?
N4 C28 H28 118.5 . . ?
C29 C28 H28 118.5 . . ?
C28 C29 C25 119.2(3) . . ?
C28 C29 H29 120.4 . . ?
C25 C29 H29 120.4 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.10
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.770
_refine_diff_density_rms         0.074

# SQUEEZE RESULTS (APPEND TO CIF)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 -0.119 0.570 0.381 1329.3 447.3
_platon_squeeze_details          
;
;
