# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_zhx
_database_code_depnum_ccdc_archive 'CCDC 1439046'
loop_
_audit_author_name
_audit_author_address
'Hua-Xin Zhang'
;Guangxi University
China
;
_audit_update_record             
;
2019-11-25 deposited with the CCDC.	2020-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H30 Cl2 Cu N5 O9'
_chemical_formula_weight         703.00

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'
Cl Cl 0.1484 0.1585 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.993(8)
_cell_length_b                   14.390(8)
_cell_length_c                   16.869(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.997(6)
_cell_angle_gamma                90
_cell_volume                     3137(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    19103
_cell_measurement_theta_min      1.86
_cell_measurement_theta_max      25.03

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_F_000             1448
_exptl_transmission_factor_min   0.831
_exptl_transmission_factor_max   0.895
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.925
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Sheldrick,1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19103
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.864
_diffrn_reflns_theta_max         31.805
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.695
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.695
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.695
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7445
_reflns_number_gt                5662
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1065P)²+0.8597P] 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         7445
_refine_ls_number_parameters     485
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1601
_refine_ls_wR_factor_gt          0.1456
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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
Cu1 Cu 0.76047(2) 0.85568(2) 0.13992(2) 0.03852(13) Uani 1 1 d . . . . .
Cl1 Cl 0.80673(7) 0.43351(5) 0.11476(5) 0.0593(2) Uani 1 1 d . . . . .
N3 N 0.83884(17) 0.97501(15) 0.12637(13) 0.0429(5) Uani 1 1 d . . . . .
N5 N 0.88346(17) 0.77620(15) 0.16096(14) 0.0443(5) Uani 1 1 d . . . . .
N2 N 0.65157(18) 0.76158(15) 0.17284(13) 0.0426(5) Uani 1 1 d . . . . .
N1 N 0.63470(16) 0.94179(14) 0.13924(13) 0.0396(5) Uani 1 1 d . . . . .
C15 C 0.5576(2) 0.79838(19) 0.19499(15) 0.0427(6) Uani 1 1 d . . . . .
N4 N 0.80842(19) 0.78459(17) 0.01770(14) 0.0481(6) Uani 1 1 d . . . . .
C19 C 0.6681(2) 1.03554(19) 0.16275(19) 0.0475(7) Uani 1 1 d . . . . .
C21 C 0.8190(3) 1.1392(2) 0.1165(2) 0.0594(9) Uani 1 1 d . . . . .
C16 C 0.5534(2) 0.9025(2) 0.19709(17) 0.0451(6) Uani 1 1 d . . . . .
C6 C 0.9288(2) 0.72210(19) 0.10264(17) 0.0447(6) Uani 1 1 d . . . . .
C20 C 0.7787(2) 1.05122(19) 0.13321(16) 0.0464(7) Uani 1 1 d . . . . .
C11 C 0.6614(3) 0.6686(2) 0.17190(19) 0.0505(7) Uani 1 1 d . . . . .
C17 C 0.6032(2) 0.9422(2) 0.05651(16) 0.0422(6) Uani 1 1 d . . . . .
C24 C 0.9410(2) 0.9845(2) 0.10647(19) 0.0514(7) Uani 1 1 d . . . . .
C3 C 0.8457(4) 0.6429(3) -0.0933(2) 0.0707(10) Uani 1 1 d . . . . .
C5 C 0.8764(2) 0.71618(19) 0.02848(17) 0.0452(6) Uani 1 1 d . . . . .
C18 C 0.5068(3) 0.9970(3) 0.04386(18) 0.0587(8) Uani 1 1 d . . . . .
C10 C 0.9261(2) 0.7820(2) 0.23033(19) 0.0575(8) Uani 1 1 d . . . . .
O4 O 0.8519(4) 0.3609(3) 0.0738(4) 0.161(2) Uani 1 1 d . . . . .
C22 C 0.9252(3) 1.1472(2) 0.0950(2) 0.0685(10) Uani 1 1 d . . . . .
C13 C 0.4850(3) 0.6476(2) 0.2166(2) 0.0653(10) Uani 1 1 d . . . . .
C9 C 1.0147(3) 0.7335(3) 0.2422(3) 0.0742(11) Uani 1 1 d . . . . .
C12 C 0.5802(3) 0.6105(2) 0.1939(2) 0.0620(9) Uani 1 1 d . . . . .
C14 C 0.4733(2) 0.7432(2) 0.21716(19) 0.0543(7) Uani 1 1 d . . . . .
C1 C 0.7623(3) 0.7821(3) -0.05048(18) 0.0611(8) Uani 1 1 d . . . . .
C23 C 0.9861(3) 1.0700(2) 0.0903(2) 0.0624(9) Uani 1 1 d . . . . .
O3 O 0.8791(3) 0.5019(2) 0.1305(2) 0.1272(16) Uani 1 1 d . . . . .
C4 C 0.8962(3) 0.6443(2) -0.0253(2) 0.0615(8) Uani 1 1 d . . . . .
H4A H 0.9456 0.5990 -0.0107 0.074 Uiso 1 1 calc R U . . .
C8 C 1.0624(3) 0.6802(3) 0.1827(3) 0.0798(12) Uani 1 1 d . . . . .
H8A H 1.1251 0.6503 0.1968 0.096 Uiso 1 1 calc R U . . .
C7 C 1.0196(3) 0.6738(3) 0.1117(3) 0.0681(9) Uani 1 1 d . . . . .
C2 C 0.7788(3) 0.7134(3) -0.1061(2) 0.0728(11) Uani 1 1 d . . . . .
O2 O 0.7370(4) 0.4739(3) 0.0661(3) 0.179(3) Uani 1 1 d . . . . .
Cl2 Cl 0.22746(8) 0.96291(8) 0.19148(7) 0.0811(3) Uani 1 1 d . . . . .
C25 C 0.3321(6) 0.7224(5) 0.0419(4) 0.153(3) Uani 1 1 d . . . . .
H25A H 0.3307 0.6672 0.0738 0.230 Uiso 1 1 calc R U . . .
H25B H 0.3463 0.7753 0.0760 0.230 Uiso 1 1 calc R U . . .
H25C H 0.2663 0.7303 0.0111 0.230 Uiso 1 1 calc R U . . .
O1 O 0.7542(3) 0.4086(4) 0.1875(2) 0.1381(16) Uani 1 1 d . . . . .
O5 O 0.1299(3) 0.9485(3) 0.2301(3) 0.1272(14) Uani 1 1 d . . . . .
C26 C 0.4222(6) 0.7128(4) -0.0178(4) 0.123(2) Uani 1 1 d . . . . .
O9 O 0.4465(6) 0.7706(3) -0.0677(4) 0.200(3) Uani 1 1 d . . . . .
C27 C 0.4832(6) 0.6290(5) -0.0211(5) 0.171(4) Uani 1 1 d . . . . .
H27A H 0.4636 0.5853 0.0176 0.256 Uiso 1 1 calc R U . . .
H27B H 0.4713 0.6023 -0.0734 0.256 Uiso 1 1 calc R U . . .
H27C H 0.5553 0.6439 -0.0097 0.256 Uiso 1 1 calc R U . . .
O6 O 0.2662(5) 1.0472(4) 0.2067(5) 0.222(3) Uani 1 1 d . . . . .
O7 O 0.2169(5) 0.9660(5) 0.1090(3) 0.202(3) Uani 1 1 d . . . . .
O8 O 0.2923(4) 0.8910(4) 0.2046(3) 0.1610(19) Uani 1 1 d . . . . .
H17B H 0.654(2) 0.959(2) 0.0213(18) 0.048(8) Uiso 1 1 d . . . . .
H17A H 0.592(2) 0.880(2) 0.0431(17) 0.042(7) Uiso 1 1 d . . . . .
H11 H 0.714(3) 0.643(2) 0.156(2) 0.055(10) Uiso 1 1 d . . . . .
H10 H 0.890(2) 0.818(2) 0.2743(17) 0.041(7) Uiso 1 1 d . . . . .
H24 H 0.978(2) 0.936(2) 0.1007(18) 0.047(8) Uiso 1 1 d . . . . .
H16B H 0.492(3) 0.928(2) 0.1895(19) 0.055(9) Uiso 1 1 d . . . . .
H16A H 0.564(2) 0.9231(19) 0.2510(17) 0.037(7) Uiso 1 1 d . . . . .
H19A H 0.658(2) 1.039(2) 0.2228(19) 0.044(8) Uiso 1 1 d . . . . .
H14 H 0.412(3) 0.769(2) 0.2330(18) 0.050(8) Uiso 1 1 d . . . . .
H23 H 1.057(3) 1.070(3) 0.072(2) 0.065(10) Uiso 1 1 d . . . . .
H7 H 1.054(3) 0.642(2) 0.067(2) 0.063(11) Uiso 1 1 d . . . . .
H21 H 0.772(3) 1.191(3) 0.122(2) 0.066(10) Uiso 1 1 d . . . . .
H19B H 0.627(3) 1.082(2) 0.1457(19) 0.054(9) Uiso 1 1 d . . . . .
H1 H 0.720(3) 0.837(3) -0.056(2) 0.068(10) Uiso 1 1 d . . . . .
H3 H 0.866(3) 0.602(3) -0.133(3) 0.086(12) Uiso 1 1 d . . . . .
H22 H 0.949(4) 1.211(4) 0.088(3) 0.113(16) Uiso 1 1 d . . . . .
H12 H 0.587(3) 0.553(3) 0.190(2) 0.072(12) Uiso 1 1 d . . . . .
H13 H 0.429(3) 0.615(3) 0.237(2) 0.074(11) Uiso 1 1 d . . . . .
H18B H 0.498(3) 1.058(3) 0.073(2) 0.081(12) Uiso 1 1 d . . . . .
H18A H 0.444(3) 0.969(2) 0.075(2) 0.067(10) Uiso 1 1 d . . . . .
H9 H 1.035(4) 0.737(3) 0.292(3) 0.090(14) Uiso 1 1 d . . . . .
H2 H 0.746(4) 0.711(3) -0.157(3) 0.109(16) 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
Cu1 N5 1.967(2) . ?
Cu1 N3 2.021(2) . ?
Cu1 N1 2.050(2) . ?
Cu1 N2 2.076(2) . ?
Cu1 N4 2.440(3) . ?
Cl1 O2 1.294(4) . ?
Cl1 O3 1.369(3) . ?
Cl1 O4 1.413(4) . ?
Cl1 O1 1.507(4) . ?
N3 C20 1.358(4) . ?
N3 C24 1.409(4) . ?
N5 C10 1.244(4) . ?
N5 C6 1.429(4) . ?
N2 C11 1.344(4) . ?
N2 C15 1.417(4) . ?
N1 C17 1.413(3) . ?
N1 C19 1.459(3) . ?
N1 C16 1.614(4) . ?
C15 C14 1.434(4) . ?
C15 C16 1.500(4) . ?
N4 C1 1.241(4) . ?
N4 C5 1.322(4) . ?
C19 C20 1.585(5) . ?
C21 C20 1.410(4) . ?
C21 C22 1.468(6) . ?
C6 C5 1.363(4) . ?
C6 C7 1.363(4) . ?
C11 C12 1.426(5) . ?
C17 C18 1.476(4) . ?
C24 C23 1.402(5) . ?
C3 C4 1.261(5) . ?
C3 C2 1.339(6) . ?
C5 C4 1.417(4) . ?
C18 C18 1.474(6) 3_675 ?
C10 C9 1.344(5) . ?
C22 C23 1.371(6) . ?
C13 C14 1.383(5) . ?
C13 C12 1.436(6) . ?
C9 C8 1.452(6) . ?
C1 C2 1.394(5) . ?
C8 C7 1.270(5) . ?
Cl2 O6 1.328(5) . ?
Cl2 O8 1.338(4) . ?
Cl2 O7 1.384(6) . ?
Cl2 O5 1.499(4) . ?
C25 C26 1.627(11) . ?
C26 O9 1.249(8) . ?
C26 C27 1.447(9) . ?

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
N5 Cu1 N3 96.03(10) . . ?
N5 Cu1 N1 169.93(9) . . ?
N3 Cu1 N1 84.06(10) . . ?
N5 Cu1 N2 97.82(10) . . ?
N3 Cu1 N2 161.79(10) . . ?
N1 Cu1 N2 80.24(10) . . ?
N5 Cu1 N4 68.55(9) . . ?
N3 Cu1 N4 94.85(9) . . ?
N1 Cu1 N4 121.50(8) . . ?
N2 Cu1 N4 101.19(9) . . ?
O2 Cl1 O3 102.8(3) . . ?
O2 Cl1 O4 108.7(4) . . ?
O3 Cl1 O4 108.3(3) . . ?
O2 Cl1 O1 106.0(4) . . ?
O3 Cl1 O1 111.9(2) . . ?
O4 Cl1 O1 117.9(3) . . ?
C20 N3 C24 120.4(2) . . ?
C20 N3 Cu1 112.04(19) . . ?
C24 N3 Cu1 127.41(19) . . ?
C10 N5 C6 120.6(3) . . ?
C10 N5 Cu1 113.8(2) . . ?
C6 N5 Cu1 125.33(17) . . ?
C11 N2 C15 117.4(3) . . ?
C11 N2 Cu1 125.3(2) . . ?
C15 N2 Cu1 117.21(17) . . ?
C17 N1 C19 108.2(2) . . ?
C17 N1 C16 117.3(2) . . ?
C19 N1 C16 110.8(2) . . ?
C17 N1 Cu1 99.02(16) . . ?
C19 N1 Cu1 110.06(17) . . ?
C16 N1 Cu1 110.91(15) . . ?
N2 C15 C14 124.4(3) . . ?
N2 C15 C16 114.5(2) . . ?
C14 C15 C16 121.1(3) . . ?
C1 N4 C5 110.9(3) . . ?
C1 N4 Cu1 130.9(2) . . ?
C5 N4 Cu1 114.94(18) . . ?
N1 C19 C20 107.4(2) . . ?
C20 C21 C22 119.8(3) . . ?
C15 C16 N1 107.9(2) . . ?
C5 C6 C7 114.5(3) . . ?
C5 C6 N5 117.6(2) . . ?
C7 C6 N5 127.9(3) . . ?
N3 C20 C21 118.7(3) . . ?
N3 C20 C19 117.4(2) . . ?
C21 C20 C19 123.9(3) . . ?
N2 C11 C12 120.5(3) . . ?
N1 C17 C18 107.4(2) . . ?
C23 C24 N3 123.7(3) . . ?
C4 C3 C2 113.7(4) . . ?
N4 C5 C6 110.0(3) . . ?
N4 C5 C4 128.2(3) . . ?
C6 C5 C4 121.7(3) . . ?
C18 C18 C17 100.9(3) 3_675 . ?
N5 C10 C9 113.3(4) . . ?
C23 C22 C21 121.0(3) . . ?
C14 C13 C12 118.1(3) . . ?
C10 C9 C8 126.3(3) . . ?
C11 C12 C13 122.2(3) . . ?
C13 C14 C15 117.5(3) . . ?
N4 C1 C2 123.5(3) . . ?
C22 C23 C24 116.4(3) . . ?
C3 C4 C5 118.8(3) . . ?
C7 C8 C9 120.9(3) . . ?
C8 C7 C6 110.9(4) . . ?
C3 C2 C1 124.9(3) . . ?
O6 Cl2 O8 117.1(4) . . ?
O6 Cl2 O7 99.2(5) . . ?
O8 Cl2 O7 100.7(4) . . ?
O6 Cl2 O5 111.3(4) . . ?
O8 Cl2 O5 111.5(3) . . ?
O7 Cl2 O5 116.2(3) . . ?
O9 C26 C27 110.5(8) . . ?
O9 C26 C25 127.6(7) . . ?
C27 C26 C25 121.8(6) . . ?

_refine_diff_density_max         0.810
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.071

