# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_t
_audit_block_doi                 10.5517/ccdc.csd.cc21hxj0
_database_code_depnum_ccdc_archive 'CCDC 1892132'
loop_
_audit_author_name
_audit_author_address
'Jin-Xiang Chen'
;Southern Medicinal Chemistry
China
;
_audit_update_record             
;
2019-01-21 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H21 Cu N3 O6'
_chemical_formula_weight         547.01

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   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   31.299(3)
_cell_length_b                   11.9822(9)
_cell_length_c                   19.7406(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 122.8270(13)
_cell_angle_gamma                90.00
_cell_volume                     6221.1(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    19649
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      28.96

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            blue
_exptl_crystal_size_max          3.0
_exptl_crystal_size_mid          2.5
_exptl_crystal_size_min          2.5
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2248
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4568
_exptl_absorpt_correction_T_max  0.6838
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      291(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            19649
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         26.37
_reflns_number_total             6316
_reflns_number_gt                5371
_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    'Diamond 3.2f (Crystal Impact GbR, 1997-2010)'
_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)+(0.0818P)²+0.0000P] 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         6316
_refine_ls_number_parameters     334
_refine_ls_number_restraints     94
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1209
_refine_ls_wR_factor_gt          0.1169
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.110
_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 0.243678(8) -0.160781(17) 0.405055(13) 0.01951(10) Uani 1 1 d U . .
O1 O 0.23502(5) -0.04987(11) 0.46902(8) 0.0257(3) Uani 1 1 d U . .
O2 O 0.25364(6) -0.15814(10) 0.57292(10) 0.0312(3) Uani 1 1 d U . .
O3 O 0.23843(6) 0.00146(12) 0.79527(9) 0.0365(3) Uani 1 1 d U . .
O4 O 0.24786(5) 0.18528(11) 0.80894(8) 0.0284(3) Uani 1 1 d U . .
O5 O 0.05966(7) 0.5610(2) 0.61991(14) 0.0851(8) Uani 1 1 d U . .
O6 O 0.14295(8) 0.5699(3) 0.68686(14) 0.0924(9) Uani 1 1 d U . .
N1 N 0.14726(7) 0.36940(13) 0.52299(11) 0.0299(4) Uani 1 1 d U . .
N2 N 0.16703(6) -0.17454(13) 0.32917(11) 0.0278(4) Uani 1 1 d U . .
N3 N -0.17905(6) -0.33390(12) -0.02140(11) 0.0262(4) Uani 1 1 d U . .
C1 C 0.23117(7) 0.02910(15) 0.57506(11) 0.0214(4) Uani 1 1 d U . .
C2 C 0.21731(7) 0.13252(15) 0.53718(12) 0.0236(4) Uani 1 1 d U . .
H2A H 0.2112 0.1404 0.4858 0.028 Uiso 1 1 calc R . .
C3 C 0.21257(7) 0.22412(15) 0.57578(11) 0.0246(4) Uani 1 1 d U . .
C4 C 0.22129(8) 0.21120(16) 0.65228(12) 0.0268(4) Uani 1 1 d U . .
H4A H 0.2193 0.2728 0.6790 0.032 Uiso 1 1 calc R . .
C5 C 0.23303(7) 0.10704(15) 0.68920(11) 0.0242(4) Uani 1 1 d U . .
C6 C 0.23788(7) 0.01578(15) 0.65010(11) 0.0233(4) Uani 1 1 d U . .
H6A H 0.2456 -0.0542 0.6743 0.028 Uiso 1 1 calc R . .
C7 C 0.24023(6) -0.06901(14) 0.53657(11) 0.0199(4) Uani 1 1 d U . .
C8 C 0.24055(7) 0.09493(16) 0.77050(11) 0.0254(4) Uani 1 1 d U . .
C9 C 0.19722(8) 0.33714(15) 0.53558(14) 0.0294(4) Uani 1 1 d U . .
H9A H 0.2228 0.3921 0.5692 0.035 Uiso 1 1 calc R . .
H9B H 0.1943 0.3342 0.4842 0.035 Uiso 1 1 calc R . .
C10 C 0.14616(8) 0.43633(16) 0.57671(13) 0.0302(4) Uani 1 1 d U . .
H10A H 0.1764 0.4656 0.6194 0.036 Uiso 1 1 calc R . .
C11 C 0.10121(8) 0.46209(19) 0.56955(14) 0.0375(5) Uani 1 1 d U . .
C12 C 0.05701(9) 0.4165(2) 0.50500(17) 0.0523(6) Uani 1 1 d U . .
H12A H 0.0259 0.4324 0.4983 0.063 Uiso 1 1 calc R . .
C13 C 0.05895(11) 0.3480(2) 0.4509(2) 0.0621(8) Uani 1 1 d U . .
H13A H 0.0292 0.3178 0.4077 0.074 Uiso 1 1 calc R . .
C14 C 0.10493(10) 0.3246(2) 0.46122(16) 0.0471(6) Uani 1 1 d U . .
H14A H 0.1066 0.2776 0.4253 0.056 Uiso 1 1 calc R . .
C15 C 0.10133(10) 0.5378(2) 0.63132(17) 0.0530(7) Uani 1 1 d U . .
C16 C 0.13428(9) -0.0947(2) 0.31912(17) 0.0503(7) Uani 1 1 d U . .
H16A H 0.1469 -0.0310 0.3510 0.060 Uiso 1 1 calc R . .
C17 C 0.08292(9) -0.1025(2) 0.2639(2) 0.0671(9) Uani 1 1 d U . .
H17A H 0.0617 -0.0451 0.2601 0.081 Uiso 1 1 calc R . .
C18 C 0.06221(9) -0.1936(2) 0.21430(18) 0.0536(7) Uani 1 1 d U . .
C19 C 0.09631(8) -0.2769(2) 0.22510(15) 0.0443(6) Uani 1 1 d U . .
H19A H 0.0846 -0.3414 0.1940 0.053 Uiso 1 1 calc R . .
C20 C 0.14741(8) -0.26382(18) 0.28176(14) 0.0366(5) Uani 1 1 d U . .
H20A H 0.1694 -0.3204 0.2872 0.044 Uiso 1 1 calc R . .
C21 C 0.00595(10) -0.1994(3) 0.1519(3) 0.0866(13) Uani 1 1 d U . .
H21A H -0.0118 -0.1635 0.1738 0.104 Uiso 1 1 calc R . .
H21B H -0.0009 -0.1561 0.1054 0.104 Uiso 1 1 calc R . .
C22 C -0.01582(9) -0.3110(3) 0.1238(2) 0.0667(9) Uani 1 1 d U . .
H22A H -0.0038 -0.3587 0.1705 0.080 Uiso 1 1 calc R . .
H22B H -0.0032 -0.3415 0.0924 0.080 Uiso 1 1 calc R . .
C23 C -0.07288(9) -0.3149(2) 0.07377(18) 0.0470(6) Uani 1 1 d U . .
C24 C -0.10188(9) -0.2564(2) 0.00244(18) 0.0549(7) Uani 1 1 d U . .
H24A H -0.0861 -0.2097 -0.0152 0.066 Uiso 1 1 calc R . .
C25 C -0.15383(8) -0.2668(2) -0.04250(15) 0.0414(5) Uani 1 1 d U . .
H25A H -0.1724 -0.2256 -0.0898 0.050 Uiso 1 1 calc R . .
C26 C -0.15121(8) -0.38874(18) 0.04856(13) 0.0317(4) Uani 1 1 d U . .
H26A H -0.1679 -0.4343 0.0653 0.038 Uiso 1 1 calc R . .
C27 C -0.09930(8) -0.3807(2) 0.09661(14) 0.0407(5) Uani 1 1 d U . .
H27A H -0.0817 -0.4199 0.1450 0.049 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 1.9506(12) . ?
Cu1 O4 1.9930(13) 6 ?
Cu1 N2 2.0322(17) . ?
Cu1 N3 2.0381(17) 8_546 ?
Cu1 O2 2.2056(13) 7_546 ?
O1 C7 1.273(2) . ?
O2 C7 1.227(2) . ?
O2 Cu1 2.2056(13) 7_546 ?
O3 C8 1.238(2) . ?
O4 C8 1.270(2) . ?
O4 Cu1 1.9930(13) 6_556 ?
O5 C15 1.229(3) . ?
O6 C15 1.224(3) . ?
N1 C10 1.345(3) . ?
N1 C14 1.334(3) . ?
N1 C9 1.495(3) . ?
N2 C16 1.336(3) . ?
N2 C20 1.332(3) . ?
N3 C26 1.339(3) . ?
N3 C25 1.341(3) . ?
N3 Cu1 2.0381(17) 8_445 ?
C1 C6 1.388(2) . ?
C1 C2 1.390(3) . ?
C1 C7 1.508(2) . ?
C2 C3 1.389(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.390(3) . ?
C3 C9 1.510(2) . ?
C4 C5 1.390(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.393(3) . ?
C5 C8 1.498(3) . ?
C6 H6A 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.371(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.387(3) . ?
C11 C15 1.518(3) . ?
C12 C13 1.373(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.369(4) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C16 C17 1.371(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.372(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.391(4) . ?
C18 C21 1.507(4) . ?
C19 C20 1.376(3) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?
C21 C22 1.466(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.501(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.383(4) . ?
C23 C27 1.384(4) . ?
C24 C25 1.372(3) . ?
C24 H24A 0.9300 . ?
C25 H25A 0.9300 . ?
C26 C27 1.370(3) . ?
C26 H26A 0.9300 . ?
C27 H27A 0.9300 . ?

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 O4 145.13(6) . 6 ?
O1 Cu1 N2 90.55(6) . . ?
O4 Cu1 N2 86.95(7) 6 . ?
O1 Cu1 N3 95.03(6) . 8_546 ?
O4 Cu1 N3 90.50(6) 6 8_546 ?
N2 Cu1 N3 173.35(6) . 8_546 ?
O1 Cu1 O2 123.12(6) . 7_546 ?
O4 Cu1 O2 91.59(6) 6 7_546 ?
N2 Cu1 O2 88.23(6) . 7_546 ?
N3 Cu1 O2 85.71(6) 8_546 7_546 ?
C7 O1 Cu1 124.84(11) . . ?
C7 O2 Cu1 159.41(14) . 7_546 ?
C8 O4 Cu1 111.10(12) . 6_556 ?
C10 N1 C14 121.58(19) . . ?
C10 N1 C9 119.65(17) . . ?
C14 N1 C9 118.61(18) . . ?
C16 N2 C20 116.51(19) . . ?
C16 N2 Cu1 123.74(15) . . ?
C20 N2 Cu1 119.57(13) . . ?
C26 N3 C25 116.79(18) . . ?
C26 N3 Cu1 125.23(14) . 8_445 ?
C25 N3 Cu1 117.93(15) . 8_445 ?
C6 C1 C2 119.96(16) . . ?
C6 C1 C7 119.16(16) . . ?
C2 C1 C7 120.87(16) . . ?
C3 C2 C1 120.28(17) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C2 C3 C4 119.44(17) . . ?
C2 C3 C9 121.22(17) . . ?
C4 C3 C9 119.34(16) . . ?
C5 C4 C3 120.66(17) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 119.42(17) . . ?
C4 C5 C8 119.48(16) . . ?
C6 C5 C8 121.10(17) . . ?
C1 C6 C5 120.13(17) . . ?
C1 C6 H6A 119.9 . . ?
C5 C6 H6A 119.9 . . ?
O2 C7 O1 125.34(16) . . ?
O2 C7 C1 118.82(16) . . ?
O1 C7 C1 115.78(15) . . ?
O3 C8 O4 124.47(17) . . ?
O3 C8 C5 120.00(17) . . ?
O4 C8 C5 115.51(17) . . ?
N1 C9 C3 108.99(15) . . ?
N1 C9 H9A 109.9 . . ?
C3 C9 H9A 109.9 . . ?
N1 C9 H9B 109.9 . . ?
C3 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
N1 C10 C11 121.1(2) . . ?
N1 C10 H10A 119.5 . . ?
C11 C10 H10A 119.5 . . ?
C10 C11 C12 117.6(2) . . ?
C10 C11 C15 119.7(2) . . ?
C12 C11 C15 122.7(2) . . ?
C11 C12 C13 120.5(2) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C14 C13 C12 119.5(3) . . ?
C14 C13 H13A 120.2 . . ?
C12 C13 H13A 120.2 . . ?
C13 C14 N1 119.7(2) . . ?
C13 C14 H14A 120.1 . . ?
N1 C14 H14A 120.1 . . ?
O6 C15 O5 127.0(3) . . ?
O6 C15 C11 116.4(2) . . ?
O5 C15 C11 116.6(2) . . ?
N2 C16 C17 122.9(2) . . ?
N2 C16 H16A 118.5 . . ?
C17 C16 H16A 118.5 . . ?
C16 C17 C18 121.2(2) . . ?
C16 C17 H17A 119.4 . . ?
C18 C17 H17A 119.4 . . ?
C17 C18 C19 115.8(2) . . ?
C17 C18 C21 120.8(2) . . ?
C19 C18 C21 123.5(2) . . ?
C20 C19 C18 120.0(2) . . ?
C20 C19 H19A 120.0 . . ?
C18 C19 H19A 120.0 . . ?
N2 C20 C19 123.5(2) . . ?
N2 C20 H20A 118.2 . . ?
C19 C20 H20A 118.2 . . ?
C22 C21 C18 116.7(3) . . ?
C22 C21 H21A 108.1 . . ?
C18 C21 H21A 108.1 . . ?
C22 C21 H21B 108.1 . . ?
C18 C21 H21B 108.1 . . ?
H21A C21 H21B 107.3 . . ?
C21 C22 C23 114.9(2) . . ?
C21 C22 H22A 108.5 . . ?
C23 C22 H22A 108.5 . . ?
C21 C22 H22B 108.5 . . ?
C23 C22 H22B 108.5 . . ?
H22A C22 H22B 107.5 . . ?
C24 C23 C27 116.3(2) . . ?
C24 C23 C22 123.0(3) . . ?
C27 C23 C22 120.7(3) . . ?
C23 C24 C25 120.4(2) . . ?
C23 C24 H24A 119.8 . . ?
C25 C24 H24A 119.8 . . ?
N3 C25 C24 123.0(2) . . ?
N3 C25 H25A 118.5 . . ?
C24 C25 H25A 118.5 . . ?
N3 C26 C27 123.0(2) . . ?
N3 C26 H26A 118.5 . . ?
C27 C26 H26A 118.5 . . ?
C26 C27 C23 120.5(2) . . ?
C26 C27 H27A 119.7 . . ?
C23 C27 H27A 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.689
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.166


# 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 0.000 0.000 -0.006 983.9 322.9
2 0.500 0.500 0.755 984.0 322.9
_platon_squeeze_details          
;
;

