# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_pp
_database_code_depnum_ccdc_archive 'CCDC 1471464'
_audit_update_record             
;
2016-03-30 deposited with the CCDC.
2017-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H11 Cu N O4'
_chemical_formula_weight         380.83

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           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   18.9711(9)
_cell_length_b                   18.9711(9)
_cell_length_c                   44.954(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     14011.3(11)
_cell_formula_units_Z            18
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.812
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3474
_exptl_absorpt_coefficient_mu    0.714
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30455
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_theta_min         1.32
_diffrn_reflns_theta_max         25.33
_reflns_number_total             5645
_reflns_number_gt                4546
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1440P)²+33.0456P] 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         5645
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.2315
_refine_ls_wR_factor_gt          0.2127
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_restrained_S_all      1.184
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.52224(3) 0.47781(3) 0.025067(9) 0.0284(2) Uani 1 1 d . . .
N1 N 0.5411(2) 0.4593(2) 0.07178(7) 0.0410(8) Uani 1 1 d . . .
O1 O 0.5548(2) 0.5916(2) 0.03439(6) 0.0536(9) Uani 1 1 d . . .
O2 O 0.4084(2) 0.4453(2) 0.03440(6) 0.0529(9) Uani 1 1 d . . .
O3 O 0.62842(18) 0.5152(2) 0.00669(6) 0.0460(8) Uani 1 1 d . . .
O4 O 0.4849(2) 0.37158(18) 0.00674(6) 0.0467(8) Uani 1 1 d . . .
C1 C 0.5974(3) 0.5228(3) 0.08710(9) 0.0507(12) Uani 1 1 d . . .
H1 H 0.6429 0.5620 0.0770 0.061 Uiso 1 1 calc R . .
C2 C 0.5916(3) 0.5336(3) 0.11736(10) 0.0591(13) Uani 1 1 d . . .
H2 H 0.6324 0.5789 0.1271 0.071 Uiso 1 1 calc R . .
C3 C 0.5241(3) 0.4757(3) 0.13285(11) 0.0564(14) Uani 1 1 d . . .
C4 C 0.4664(3) 0.4082(3) 0.11733(10) 0.0592(14) Uani 1 1 d . . .
H4 H 0.4210 0.3673 0.1270 0.071 Uiso 1 1 calc R . .
C5 C 0.4774(3) 0.4027(3) 0.08703(9) 0.0507(12) Uani 1 1 d . . .
H5 H 0.4384 0.3572 0.0768 0.061 Uiso 1 1 calc R . .
C6 C 0.5115(4) 0.4888(4) 0.16457(11) 0.0686(16) Uani 1 1 d . . .
C11 C 0.6403(3) 0.5437(3) -0.01925(9) 0.0383(9) Uani 1 1 d . . .
C12 C 0.7190(3) 0.5640(3) -0.03386(9) 0.0453(11) Uani 1 1 d . . .
C13 C 0.7748(3) 0.5497(3) -0.01951(9) 0.0399(9) Uani 1 1 d . . .
H13 H 0.7651 0.5302 -0.0001 0.048 Uiso 1 1 calc R . .
C14 C 0.7344(3) 0.5947(4) -0.06297(10) 0.0554(13) Uani 1 1 d . . .
H14 H 0.6971 0.6053 -0.0725 0.067 Uiso 1 1 calc R . .
C15 C 0.4563(3) 0.3600(3) -0.01923(9) 0.0391(9) Uani 1 1 d . . .
C16 C 0.4360(3) 0.2811(3) -0.03382(9) 0.0438(10) Uani 1 1 d . . .
C17 C 0.4053(4) 0.2657(3) -0.06294(10) 0.0549(13) Uani 1 1 d . . .
H17 H 0.3946 0.3029 -0.0724 0.066 Uiso 1 1 calc R . .
C18 C 0.8047(3) 0.6093(4) -0.07770(11) 0.0600(15) Uani 1 1 d . . .
C19 C 0.8196(3) 0.6392(4) -0.10902(11) 0.0647(16) Uani 1 1 d . . .
C7A C 0.5385(11) 0.5655(9) 0.1747(3) 0.095(5) Uani 0.50 1 d P . .
C8A C 0.4348(9) 0.4615(11) 0.1748(3) 0.096(6) Uani 0.50 1 d P . .
C7B C 0.5791(7) 0.5288(9) 0.1842(2) 0.073(4) Uani 0.50 1 d P . .
C8B C 0.4707(9) 0.4204(7) 0.1843(2) 0.072(4) Uani 0.50 1 d P . .
C9A C 0.5647(7) 0.5407(8) 0.2138(2) 0.067(3) Uani 0.50 1 d P . .
C9B C 0.7533(8) 0.6105(12) -0.1285(2) 0.092(5) Uani 0.50 1 d P . .
C10A C 0.8976(8) 0.6904(10) -0.1196(2) 0.069(3) Uani 0.50 1 d P . .
C10B C 0.8569(10) 0.6099(13) -0.1285(2) 0.096(6) Uani 0.50 1 d P . .


_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 O3 1.953(3) . ?
Cu1 O4 1.953(3) . ?
Cu1 O1 1.971(3) . ?
Cu1 O2 1.971(3) . ?
Cu1 N1 2.188(3) . ?
Cu1 Cu1 2.6853(8) 10_665 ?
N1 C1 1.333(6) . ?
N1 C5 1.336(6) . ?
O1 C15 1.244(5) 10_665 ?
O2 C11 1.247(5) 10_665 ?
O3 C11 1.257(5) . ?
O4 C15 1.260(5) . ?
C1 C2 1.388(6) . ?
C2 C3 1.387(7) . ?
C3 C4 1.387(7) . ?
C3 C6 1.487(7) . ?
C4 C5 1.390(6) . ?
C6 C8A 1.356(16) . ?
C6 C7A 1.357(16) . ?
C6 C7B 1.423(12) . ?
C6 C8B 1.437(12) . ?
C11 O2 1.247(5) 10_665 ?
C11 C12 1.495(6) . ?
C12 C13 1.379(6) . ?
C12 C14 1.402(6) . ?
C13 C16 1.378(6) 3_665 ?
C14 C18 1.387(7) . ?
C15 O1 1.244(5) 10_665 ?
C15 C16 1.497(6) . ?
C16 C13 1.379(6) 2_655 ?
C16 C17 1.403(6) . ?
C17 C18 1.388(7) 2_655 ?
C18 C17 1.388(7) 3_665 ?
C18 C19 1.491(7) . ?
C19 C10A 1.385(14) . ?
C19 C9A 1.393(13) 8_654 ?
C19 C9B 1.399(13) . ?
C19 C10B 1.404(13) . ?
C7A C7B 1.34(2) . ?
C7A C9B 1.439(15) 6_565 ?
C7A C9A 1.95(2) . ?
C7A C8A 1.97(2) . ?
C8A C8B 1.34(2) . ?
C8A C10B 1.438(15) 6_565 ?
C8A C10A 1.94(2) 6_565 ?
C7B C9A 1.397(14) . ?
C7B C9B 1.98(2) 6_565 ?
C8B C10A 1.397(14) 6_565 ?
C8B C10B 1.99(2) 6_565 ?
C9A C9B 1.38(2) 6_565 ?
C9A C19 1.394(13) 6_565 ?
C9A C10A 1.993(17) 6_565 ?
C9B C9A 1.38(2) 8_654 ?
C9B C7A 1.439(15) 8_654 ?
C9B C10B 1.971(18) . ?
C9B C7B 1.98(2) 8_654 ?
C10A C10B 1.38(2) . ?
C10A C8B 1.397(14) 8_654 ?
C10A C8A 1.94(2) 8_654 ?
C10A C9A 1.993(17) 8_654 ?
C10B C8A 1.438(15) 8_654 ?
C10B C8B 1.99(2) 8_654 ?

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
O3 Cu1 O4 88.39(15) . . ?
O3 Cu1 O1 89.47(16) . . ?
O4 Cu1 O1 166.75(12) . . ?
O3 Cu1 O2 166.66(12) . . ?
O4 Cu1 O2 89.53(16) . . ?
O1 Cu1 O2 89.54(17) . . ?
O3 Cu1 N1 104.03(13) . . ?
O4 Cu1 N1 104.09(13) . . ?
O1 Cu1 N1 89.11(13) . . ?
O2 Cu1 N1 89.25(13) . . ?
O3 Cu1 Cu1 87.70(8) . 10_665 ?
O4 Cu1 Cu1 87.77(8) . 10_665 ?
O1 Cu1 Cu1 79.08(8) . 10_665 ?
O2 Cu1 Cu1 79.05(8) . 10_665 ?
N1 Cu1 Cu1 163.35(10) . 10_665 ?
C1 N1 C5 117.0(4) . . ?
C1 N1 Cu1 118.2(3) . . ?
C5 N1 Cu1 117.8(3) . . ?
C15 O1 Cu1 128.1(3) 10_665 . ?
C11 O2 Cu1 128.2(3) 10_665 . ?
C11 O3 Cu1 118.6(3) . . ?
C15 O4 Cu1 118.3(3) . . ?
N1 C1 C2 123.5(5) . . ?
C3 C2 C1 119.0(5) . . ?
C2 C3 C4 117.9(4) . . ?
C2 C3 C6 120.8(5) . . ?
C4 C3 C6 121.2(5) . . ?
C3 C4 C5 118.9(5) . . ?
N1 C5 C4 123.5(5) . . ?
C8A C6 C7A 93.1(11) . . ?
C8A C6 C7B 120.1(8) . . ?
C7A C6 C7B 57.6(9) . . ?
C8A C6 C8B 57.1(9) . . ?
C7A C6 C8B 120.4(7) . . ?
C7B C6 C8B 91.9(9) . . ?
C8A C6 C3 119.5(7) . . ?
C7A C6 C3 119.6(7) . . ?
C7B C6 C3 120.4(7) . . ?
C8B C6 C3 119.9(6) . . ?
O2 C11 O3 126.2(4) 10_665 . ?
O2 C11 C12 116.5(4) 10_665 . ?
O3 C11 C12 117.3(3) . . ?
C13 C12 C14 119.8(4) . . ?
C13 C12 C11 120.7(4) . . ?
C14 C12 C11 119.4(4) . . ?
C12 C13 C16 120.4(4) . 3_665 ?
C18 C14 C12 120.6(4) . . ?
O1 C15 O4 126.6(4) 10_665 . ?
O1 C15 C16 116.4(4) 10_665 . ?
O4 C15 C16 117.0(3) . . ?
C13 C16 C17 119.7(4) 2_655 . ?
C13 C16 C15 120.9(4) 2_655 . ?
C17 C16 C15 119.3(4) . . ?
C18 C17 C16 120.6(4) 2_655 . ?
C14 C18 C17 118.9(4) . 3_665 ?
C14 C18 C19 120.5(4) . . ?
C17 C18 C19 120.6(4) 3_665 . ?
C10A C19 C9A 91.7(9) . 8_654 ?
C10A C19 C9B 119.7(7) . . ?
C9A C19 C9B 59.1(9) 8_654 . ?
C10A C19 C10B 59.4(9) . . ?
C9A C19 C10B 119.9(7) 8_654 . ?
C9B C19 C10B 89.4(10) . . ?
C10A C19 C18 121.5(6) . . ?
C9A C19 C18 121.5(6) 8_654 . ?
C9B C19 C18 118.7(7) . . ?
C10B C19 C18 118.5(7) . . ?
C7B C7A C6 63.7(10) . . ?
C7B C7A C9B 90.9(13) . 6_565 ?
C6 C7A C9B 121.1(11) . 6_565 ?
C7B C7A C9A 45.9(8) . . ?
C6 C7A C9A 92.8(10) . . ?
C9B C7A C9A 45.0(9) 6_565 . ?
C7B C7A C8A 91.4(11) . . ?
C6 C7A C8A 43.4(7) . . ?
C9B C7A C8A 89.9(9) 6_565 . ?
C9A C7A C8A 90.2(8) . . ?
C8B C8A C6 64.5(10) . . ?
C8B C8A C10B 91.5(14) . 6_565 ?
C6 C8A C10B 121.6(11) . 6_565 ?
C8B C8A C10A 46.1(8) . 6_565 ?
C6 C8A C10A 93.1(11) . 6_565 ?
C10B C8A C10A 45.4(9) 6_565 6_565 ?
C8B C8A C7A 92.3(11) . . ?
C6 C8A C7A 43.4(7) . . ?
C10B C8A C7A 90.1(9) 6_565 . ?
C10A C8A C7A 90.5(8) 6_565 . ?
C7A C7B C9A 90.6(12) . . ?
C7A C7B C6 58.7(8) . . ?
C9A C7B C6 118.6(10) . . ?
C7A C7B C9B 46.6(8) . 6_565 ?
C9A C7B C9B 44.0(8) . 6_565 ?
C6 C7B C9B 89.7(9) . 6_565 ?
C8A C8B C10A 90.3(12) . 6_565 ?
C8A C8B C6 58.4(8) . . ?
C10A C8B C6 117.7(10) 6_565 . ?
C8A C8B C10B 46.3(8) . 6_565 ?
C10A C8B C10B 44.0(8) 6_565 6_565 ?
C6 C8B C10B 89.4(9) . 6_565 ?
C9B C9A C19 60.6(8) 6_565 6_565 ?
C9B C9A C7B 91.1(11) 6_565 . ?
C19 C9A C7B 121.6(10) 6_565 . ?
C9B C9A C7A 47.6(8) 6_565 . ?
C19 C9A C7A 92.3(9) 6_565 . ?
C7B C9A C7A 43.5(8) . . ?
C9B C9A C10A 89.2(9) 6_565 6_565 ?
C19 C9A C10A 44.0(6) 6_565 6_565 ?
C7B C9A C10A 91.0(8) . 6_565 ?
C7A C9A C10A 89.5(7) . 6_565 ?
C9A C9B C19 60.3(9) 8_654 . ?
C9A C9B C7A 87.4(14) 8_654 8_654 ?
C19 C9B C7A 118.5(12) . 8_654 ?
C9A C9B C10B 90.9(10) 8_654 . ?
C19 C9B C10B 45.4(6) . . ?
C7A C9B C10B 90.1(9) 8_654 . ?
C9A C9B C7B 44.8(8) 8_654 8_654 ?
C19 C9B C7B 90.5(10) . 8_654 ?
C7A C9B C7B 42.6(9) 8_654 8_654 ?
C10B C9B C7B 91.3(8) . 8_654 ?
C10B C10A C19 61.0(8) . . ?
C10B C10A C8B 91.3(11) . 8_654 ?
C19 C10A C8B 122.4(10) . 8_654 ?
C10B C10A C8A 47.8(8) . 8_654 ?
C19 C10A C8A 92.7(9) . 8_654 ?
C8B C10A C8A 43.6(8) 8_654 8_654 ?
C10B C10A C9A 89.8(9) . 8_654 ?
C19 C10A C9A 44.3(6) . 8_654 ?
C8B C10A C9A 91.6(8) 8_654 8_654 ?
C8A C10A C9A 89.8(7) 8_654 8_654 ?
C10A C10B C19 59.6(9) . . ?
C10A C10B C8A 86.8(14) . 8_654 ?
C19 C10B C8A 117.9(12) . 8_654 ?
C10A C10B C9B 90.0(10) . . ?
C19 C10B C9B 45.2(6) . . ?
C8A C10B C9B 89.9(9) 8_654 . ?
C10A C10B C8B 44.6(8) . 8_654 ?
C19 C10B C8B 90.2(10) . 8_654 ?
C8A C10B C8B 42.2(9) 8_654 8_654 ?
C9B C10B C8B 91.2(8) . 8_654 ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.33
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         2.212
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.203
