# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1982845'
loop_
_audit_author_name
_audit_author_address
Alamgir
;Beijing University of Technology
China
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2021-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H26 N4 O7 Zn'
_chemical_formula_weight         547.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 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, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   9.9904(6)
_cell_length_b                   6.0482(5)
_cell_length_c                   21.616(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.289(8)
_cell_angle_gamma                90
_cell_volume                     1280.86(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6828
_cell_measurement_theta_min      4.171
_cell_measurement_theta_max      65.026

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.762
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6828
_diffrn_reflns_av_unetI/netI     0.0825
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.171
_diffrn_reflns_theta_max         65.026
_diffrn_reflns_theta_full        65.026
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2187
_reflns_number_gt                1541
_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       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0903P)²+1.0016P] 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         2187
_refine_ls_number_parameters     164
_refine_ls_number_restraints     142
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0711
_refine_ls_wR_factor_ref         0.1948
_refine_ls_wR_factor_gt          0.1710
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.039
_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
C1 C 0.7608(5) 1.2492(10) 0.7530(2) 0.0323(12) Uani 1 1 d . U . . .
C2 C 0.8912(5) 1.3630(9) 0.7502(2) 0.0328(12) Uani 1 1 d . U . . .
C3 C 0.9295(5) 1.5767(9) 0.7502(3) 0.0401(13) Uani 1 1 d . U . . .
H3 H 0.873936 1.699946 0.750357 0.048 Uiso 1 1 calc R U . . .
C4 C 0.5514(6) 1.0066(11) 0.6267(3) 0.0493(15) Uani 1 1 d . U . . .
H4 H 0.600839 1.137424 0.628141 0.059 Uiso 1 1 calc R U . . .
C5 C 0.5504(7) 0.8602(12) 0.5767(3) 0.0605(18) Uani 1 1 d . U . . .
H5 H 0.599756 0.893406 0.545588 0.073 Uiso 1 1 calc R U . . .
C6 C 0.4764(7) 0.6661(11) 0.5733(3) 0.0541(16) Uani 1 1 d . U . . .
C7 C 0.4070(6) 0.6260(10) 0.6205(3) 0.0499(15) Uani 1 1 d . U . . .
H7 H 0.355332 0.497747 0.619937 0.060 Uiso 1 1 calc R U . . .
C8 C 0.4133(6) 0.7743(10) 0.6687(3) 0.0447(14) Uani 1 1 d . U . . .
H8 H 0.366351 0.741816 0.700767 0.054 Uiso 1 1 calc R U . . .
C9 C 0.4659(7) 0.4991(14) 0.5205(3) 0.0672(19) Uani 1 1 d . U . . .
H9 H 0.402401 0.385884 0.519300 0.081 Uiso 1 1 calc R U . . .
C10 C 0.9581(11) 0.9205(16) 0.6125(4) 0.118(4) Uani 1 1 d . U . . .
H10A H 0.867104 0.948364 0.618763 0.176 Uiso 1 1 calc R U . . .
H10B H 0.958062 0.791899 0.586452 0.176 Uiso 1 1 calc R U . . .
H10C H 1.017317 0.895881 0.652574 0.176 Uiso 1 1 calc R U . . .
C11 C 0.9169(15) 1.291(2) 0.5699(5) 0.163(5) Uani 1 1 d . U . . .
H11A H 0.832823 1.257912 0.583202 0.244 Uiso 1 1 calc R U . . .
H11B H 0.958998 1.417159 0.592622 0.244 Uiso 1 1 calc R U . . .
H11C H 0.898581 1.321958 0.525510 0.244 Uiso 1 1 calc R U . . .
C12 C 1.1347(13) 1.117(3) 0.5668(6) 0.163(5) Uani 1 1 d . U . . .
H12 H 1.192048 1.005462 0.586235 0.195 Uiso 1 1 calc R U . . .
N1 N 0.4832(4) 0.9631(8) 0.67220(19) 0.0361(11) Uani 1 1 d . U . . .
N2 N 1.0056(10) 1.1071(14) 0.5823(3) 0.101(2) Uani 1 1 d . U . . .
O1 O 0.6553(3) 1.3669(6) 0.74782(17) 0.0375(9) Uani 1 1 d . U . . .
O2 O 0.7605(4) 1.0453(7) 0.7578(2) 0.0513(11) Uani 1 1 d . U . . .
O3 O 1.000000 1.2262(8) 0.750000 0.0328(12) Uani 1 2 d S TU P . .
O4 O 1.1869(10) 1.228(2) 0.5363(5) 0.250(7) Uani 1 1 d . U . . .
Zn1 Zn 0.500000 1.16352(16) 0.750000 0.0319(4) Uani 1 2 d S TU 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
C1 O2 1.237(7) . ?
C1 O1 1.258(6) . ?
C1 C2 1.486(7) . ?
C2 C3 1.348(7) . ?
C2 O3 1.367(6) . ?
C3 C3 1.409(10) 2_756 ?
C3 H3 0.9300 . ?
C4 N1 1.328(7) . ?
C4 C5 1.395(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.364(9) . ?
C6 C9 1.512(9) . ?
C7 C8 1.367(8) . ?
C7 H7 0.9300 . ?
C8 N1 1.333(7) . ?
C8 H8 0.9300 . ?
C9 C9 1.221(12) 3_666 ?
C9 H9 0.9300 . ?
C10 N2 1.431(11) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 N2 1.414(13) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O4 1.136(13) . ?
C12 N2 1.396(14) . ?
C12 H12 0.9300 . ?
N1 Zn1 2.053(4) . ?
O1 Zn1 1.988(3) . ?

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
O2 C1 O1 123.8(5) . . ?
O2 C1 C2 118.8(5) . . ?
O1 C1 C2 117.4(5) . . ?
C3 C2 O3 110.8(4) . . ?
C3 C2 C1 134.1(5) . . ?
O3 C2 C1 115.1(4) . . ?
C2 C3 C3 106.5(3) . 2_756 ?
C2 C3 H3 126.7 . . ?
C3 C3 H3 126.7 2_756 . ?
N1 C4 C5 121.4(6) . . ?
N1 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 120.2(6) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C7 C6 C5 117.2(6) . . ?
C7 C6 C9 118.4(6) . . ?
C5 C6 C9 124.4(6) . . ?
C6 C7 C8 120.0(6) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
N1 C8 C7 123.4(6) . . ?
N1 C8 H8 118.3 . . ?
C7 C8 H8 118.3 . . ?
C9 C9 C6 125.2(11) 3_666 . ?
C9 C9 H9 117.4 3_666 . ?
C6 C9 H9 117.4 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 N2 135.7(17) . . ?
O4 C12 H12 112.1 . . ?
N2 C12 H12 112.1 . . ?
C4 N1 C8 117.9(5) . . ?
C4 N1 Zn1 121.2(4) . . ?
C8 N1 Zn1 120.6(4) . . ?
C12 N2 C11 119.7(11) . . ?
C12 N2 C10 123.2(12) . . ?
C11 N2 C10 117.1(10) . . ?
C1 O1 Zn1 106.9(3) . . ?
C2 O3 C2 105.5(5) . 2_756 ?
O1 Zn1 O1 103.5(2) 2_656 . ?
O1 Zn1 N1 116.48(16) 2_656 . ?
O1 Zn1 N1 106.55(16) . . ?
O1 Zn1 N1 106.55(16) 2_656 2_656 ?
O1 Zn1 N1 116.48(16) . 2_656 ?
N1 Zn1 N1 107.6(3) . 2_656 ?

_refine_diff_density_max         0.813
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.095

