# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_Ga-DES
_database_code_depnum_ccdc_archive 'CCDC 1944424'
loop_
_audit_author_name
_audit_author_address
'Junbiao Wu'
;northeastern university
China
;
_audit_update_record             
;
2019-07-31 deposited with the CCDC.	2020-10-29 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            'C40 H28 Ga2 N6 O20'
_chemical_formula_weight         1052.12

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'
Ga Ga 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -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                   26.47(5)
_cell_length_b                   10.667(19)
_cell_length_c                   17.28(3)
_cell_angle_alpha                90
_cell_angle_beta                 125.389(18)
_cell_angle_gamma                90
_cell_volume                     3976(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293
_cell_measurement_reflns_used    3690
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_F_000             2128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    1.453
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.703
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Graphite Monochromator'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 13.6612
_diffrn_reflns_number            17943
_diffrn_reflns_av_unetI/netI     0.1063
_diffrn_reflns_av_R_equivalents  0.1313
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.888
_diffrn_reflns_theta_max         27.600
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4593
_reflns_number_gt                2837
_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)+(0.1151P)²+7.0278P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4593
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1349
_refine_ls_R_factor_gt           0.0890
_refine_ls_wR_factor_ref         0.2599
_refine_ls_wR_factor_gt          0.2226
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_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
Ga1 Ga 0.13066(3) 0.73537(7) 0.34810(5) 0.0371(3) Uani 1 1 d . . . . .
O1 O 0.0678(2) 0.6352(5) 0.3452(3) 0.0430(11) Uani 1 1 d . . . . .
O2 O 0.0911(2) 0.8348(5) 0.2316(3) 0.0440(12) Uani 1 1 d . . . . .
O3 O 0.1455(2) 0.6144(5) 0.2796(3) 0.0448(12) Uani 1 1 d . . . . .
O4 O 0.1917(2) 0.6436(4) 0.4733(3) 0.0407(11) Uani 1 1 d . . . . .
O5 O 0.2103(2) 0.8387(4) 0.3967(3) 0.0402(11) Uani 1 1 d . . . . .
O6 O 0.1100(2) 0.8630(5) 0.4055(4) 0.0471(12) Uani 1 1 d . . . . .
O7 O 0.0949(3) 0.8453(5) 0.1055(4) 0.0536(14) Uani 1 1 d . . . . .
O8 O 0.0216(3) 0.6336(5) 0.4207(4) 0.0561(14) Uani 1 1 d . . . . .
O9 O 0.1389(3) 0.6034(5) 0.1438(4) 0.0625(16) Uani 1 1 d . . . . .
O10 O 0.0556(3) 0.8822(5) 0.4662(4) 0.0528(13) Uani 1 1 d . . . . .
N3 N 0.0251(3) 0.2326(7) 0.0730(4) 0.0496(15) Uani 1 1 d . . . . .
N1 N 0.1457(3) 0.2579(6) 0.5102(4) 0.0491(15) Uani 1 1 d . . . . .
H1B H 0.1376 0.2647 0.5515 0.059 Uiso 1 1 calc R U . . .
N2 N 0.2025(3) 0.1940(8) 0.1603(5) 0.0624(19) Uani 1 1 d . . . . .
H2B H 0.2088 0.1864 0.1170 0.075 Uiso 1 1 calc R U . . .
C1 C 0.1814(5) 0.3246(9) 0.2522(6) 0.064(2) Uani 1 1 d . . . . .
H1A H 0.1739 0.4046 0.2647 0.077 Uiso 1 1 calc R U . . .
C2 C 0.2042(4) 0.0964(9) 0.2078(6) 0.060(2) Uani 1 1 d . . . . .
H2A H 0.2120 0.0179 0.1935 0.072 Uiso 1 1 calc R U . . .
C3 C 0.1949(4) 0.1059(7) 0.2786(6) 0.054(2) Uani 1 1 d . . . . .
H3A H 0.1962 0.0338 0.3101 0.065 Uiso 1 1 calc R U . . .
C5 C 0.1907(5) 0.3056(10) 0.1816(7) 0.069(3) Uani 1 1 d . . . . .
H5A H 0.1885 0.3749 0.1471 0.082 Uiso 1 1 calc R U . . .
C6 C 0.1577(4) 0.3617(8) 0.4794(6) 0.055(2) Uani 1 1 d . . . . .
H6A H 0.1571 0.4402 0.5023 0.066 Uiso 1 1 calc R U . . .
C7 C 0.1711(4) 0.3505(7) 0.4132(5) 0.0483(18) Uani 1 1 d . . . . .
H7A H 0.1799 0.4222 0.3925 0.058 Uiso 1 1 calc R U . . .
C8 C 0.1590(4) 0.1292(7) 0.4125(5) 0.0490(18) Uani 1 1 d . . . . .
H8A H 0.1596 0.0493 0.3915 0.059 Uiso 1 1 calc R U . . .
C9 C 0.1461(4) 0.1441(7) 0.4780(5) 0.0501(18) Uani 1 1 d . . . . .
H9A H 0.1374 0.0740 0.5004 0.060 Uiso 1 1 calc R U . . .
C10 C 0.1715(3) 0.2343(7) 0.3768(5) 0.0398(15) Uani 1 1 d . . . . .
C11 C 0.0738(3) 0.8227(7) 0.4276(5) 0.0411(16) Uani 1 1 d . . . . .
C12 C 0.1834(3) 0.2217(7) 0.3041(5) 0.0418(16) Uani 1 1 d . . . . .
C13 C 0.0029(4) 0.3456(7) 0.1672(6) 0.0506(18) Uani 1 1 d . . . . .
H13A H -0.0060 0.4214 0.1835 0.061 Uiso 1 1 calc R U . . .
C14 C 0.0298(4) 0.1252(8) 0.1157(5) 0.0493(18) Uani 1 1 d . . . . .
H14A H 0.0389 0.0510 0.0979 0.059 Uiso 1 1 calc R U . . .
C15 C 0.0133(4) 0.3419(8) 0.0981(6) 0.055(2) Uani 1 1 d . . . . .
H15A H 0.0122 0.4156 0.0685 0.066 Uiso 1 1 calc R U . . .
C16 C 0.0208(3) 0.1256(7) 0.1867(5) 0.0449(16) Uani 1 1 d . . . . .
H16A H 0.0252 0.0509 0.2178 0.054 Uiso 1 1 calc R U . . .
C17 C 0.0056(3) 0.2336(6) 0.2134(5) 0.0382(15) Uani 1 1 d . . . . .
C18 C 0.1303(4) 0.6587(7) 0.1976(5) 0.0453(17) Uani 1 1 d . . . . .
C19 C 0.2553(3) 0.8077(6) 0.4767(5) 0.0367(14) Uani 1 1 d . . . . .
C20 C 0.0518(3) 0.6842(7) 0.3966(5) 0.0417(15) Uani 1 1 d . . . . .
C4 C 0.1034(3) 0.7941(7) 0.1747(5) 0.0418(16) Uani 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
Ga1 O3 1.939(5) . ?
Ga1 O6 1.940(6) . ?
Ga1 O1 1.952(6) . ?
Ga1 O2 1.957(6) . ?
Ga1 O4 2.049(5) . ?
Ga1 O5 2.076(6) . ?
O1 C20 1.296(8) . ?
O2 C4 1.278(9) . ?
O3 C18 1.315(9) . ?
O4 C19 1.257(8) 7_566 ?
O5 C19 1.237(8) . ?
O6 C11 1.292(9) . ?
O7 C4 1.211(9) . ?
O8 C20 1.220(9) . ?
O9 C18 1.229(9) . ?
O10 C11 1.205(9) . ?
N3 C14 1.329(10) . ?
N3 C15 1.343(11) . ?
N1 C9 1.338(10) . ?
N1 C6 1.345(10) . ?
N2 C2 1.310(11) . ?
N2 C5 1.336(12) . ?
C1 C5 1.392(12) . ?
C1 C12 1.398(11) . ?
C2 C3 1.385(11) . ?
C3 C12 1.401(11) . ?
C6 C7 1.383(11) . ?
C7 C10 1.394(10) . ?
C8 C9 1.367(11) . ?
C8 C10 1.408(10) . ?
C10 C12 1.467(10) . ?
C11 C20 1.564(11) . ?
C13 C15 1.372(11) . ?
C13 C17 1.415(10) . ?
C14 C16 1.377(10) . ?
C16 C17 1.385(10) . ?
C17 C17 1.459(14) 2 ?
C18 C4 1.555(11) . ?
C19 O4 1.257(8) 7_566 ?
C19 C19 1.582(13) 7_566 ?

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 Ga1 O6 174.8(2) . . ?
O3 Ga1 O1 95.2(2) . . ?
O6 Ga1 O1 84.8(2) . . ?
O3 Ga1 O2 84.8(3) . . ?
O6 Ga1 O2 90.2(3) . . ?
O1 Ga1 O2 109.2(2) . . ?
O3 Ga1 O4 90.7(2) . . ?
O6 Ga1 O4 94.6(3) . . ?
O1 Ga1 O4 84.6(2) . . ?
O2 Ga1 O4 165.8(2) . . ?
O3 Ga1 O5 94.8(2) . . ?
O6 Ga1 O5 86.7(2) . . ?
O1 Ga1 O5 161.9(2) . . ?
O2 Ga1 O5 86.7(2) . . ?
O4 Ga1 O5 80.3(2) . . ?
C20 O1 Ga1 111.9(4) . . ?
C4 O2 Ga1 112.5(5) . . ?
C18 O3 Ga1 112.0(5) . . ?
C19 O4 Ga1 114.4(4) 7_566 . ?
C19 O5 Ga1 113.9(4) . . ?
C11 O6 Ga1 113.2(5) . . ?
C14 N3 C15 122.2(7) . . ?
C9 N1 C6 121.5(7) . . ?
C2 N2 C5 117.6(8) . . ?
C5 C1 C12 119.2(9) . . ?
N2 C2 C3 122.5(8) . . ?
C2 C3 C12 121.5(8) . . ?
N2 C5 C1 124.0(9) . . ?
N1 C6 C7 119.2(7) . . ?
C6 C7 C10 121.6(7) . . ?
C9 C8 C10 120.3(7) . . ?
N1 C9 C8 121.0(7) . . ?
C7 C10 C8 116.3(7) . . ?
C7 C10 C12 122.1(7) . . ?
C8 C10 C12 121.6(7) . . ?
O10 C11 O6 126.2(7) . . ?
O10 C11 C20 119.9(6) . . ?
O6 C11 C20 113.9(6) . . ?
C1 C12 C3 115.2(8) . . ?
C1 C12 C10 122.0(7) . . ?
C3 C12 C10 122.8(7) . . ?
C15 C13 C17 119.7(8) . . ?
N3 C14 C16 119.0(7) . . ?
N3 C15 C13 120.5(7) . . ?
C14 C16 C17 122.1(7) . . ?
C16 C17 C13 116.4(7) . . ?
C16 C17 C17 122.2(5) . 2 ?
C13 C17 C17 121.3(5) . 2 ?
O9 C18 O3 124.5(7) . . ?
O9 C18 C4 120.7(7) . . ?
O3 C18 C4 114.6(6) . . ?
O5 C19 O4 128.8(6) . 7_566 ?
O5 C19 C19 116.0(7) . 7_566 ?
O4 C19 C19 115.2(7) 7_566 7_566 ?
O8 C20 O1 126.5(7) . . ?
O8 C20 C11 119.3(6) . . ?
O1 C20 C11 114.3(6) . . ?
O7 C4 O2 128.4(7) . . ?
O7 C4 C18 117.8(7) . . ?
O2 C4 C18 113.8(6) . . ?

_refine_diff_density_max         1.406
_refine_diff_density_min         -1.147
_refine_diff_density_rms         0.177

