# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc20hqw4
_database_code_depnum_ccdc_archive 'CCDC 1862166'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/jacs.9b04173 2019
loop_
_audit_author_name
_audit_author_address
'farzane rouhani' 'Tarbiat modares university'
_audit_update_record             
;
2018-08-15 deposited with the CCDC.	2019-07-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H15 N2 O5 Zn'
_chemical_formula_weight         440.72

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           73
_space_group_name_H-M_alt        'I b c a'
_space_group_name_Hall           '-I 2b 2c'

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

_cell_length_a                   17.6350(15)
_cell_length_b                   22.345(2)
_cell_length_c                   22.944(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     9041.2(14)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9676
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      30.88

_exptl_crystal_description       block
_exptl_crystal_colour            orange-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_F_000             3600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.34
_exptl_absorpt_coefficient_mu    1.117
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6892
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7394
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.775
_diffrn_reflns_theta_max         31.691
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7394
_reflns_number_gt                5268
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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-2016/6 (Sheldrick, 2016)'
_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)+(0.0440P)²+21.3378P] 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         7394
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1323
_refine_ls_wR_factor_gt          0.1080
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.001

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
Zn1 Zn 0.05591(2) 0.00521(2) 0.04800(2) 0.03414(8) Uani 1 1 d . . . . .
O5 O -0.29695(13) 0.22130(10) 0.17206(9) 0.0638(6) Uani 1 1 d . . . . .
N2 N 0.39928(12) 0.02595(14) 0.19401(10) 0.0591(7) Uani 1 1 d . . . . .
H2B H 0.404604 0.006968 0.163702 0.071 Uiso 1 1 calc R U . . .
O3 O -0.02669(12) 0.05296(10) 0.08994(9) 0.0578(5) Uani 1 1 d . . . . .
C3 C 0.06196(14) 0.16809(11) -0.13204(11) 0.0420(5) Uani 1 1 d . . . . .
H3 H 0.017573 0.152224 -0.147534 0.050 Uiso 1 1 calc R U . . .
C13 C -0.14388(16) 0.10402(11) 0.09531(11) 0.0438(5) Uani 1 1 d . . . . .
C4 C 0.15687(15) 0.16988(11) -0.05701(11) 0.0436(5) Uani 1 1 d . . . . .
H4 H 0.175648 0.155619 -0.021765 0.052 Uiso 1 1 calc R U . . .
O4 O 0.10726(13) -0.04479(10) -0.01561(9) 0.0619(5) Uani 1 1 d . . . . .
C1 C 0.05237(13) 0.09453(10) -0.04936(10) 0.0356(4) Uani 1 1 d . . . . .
N1 N 0.14238(11) 0.00874(9) 0.10603(9) 0.0385(4) Uani 1 1 d . . . . .
O2 O 0.07898(10) 0.07889(8) -0.00099(8) 0.0453(4) Uani 1 1 d . . . . .
C7 C 0.16644(16) 0.23595(12) -0.13864(11) 0.0472(6) Uani 1 1 d . . . . .
O1 O 0.00274(11) -0.07043(8) 0.07503(8) 0.0501(5) Uani 1 1 d . . . . .
C19 C 0.26522(12) 0.00965(11) 0.18367(10) 0.0367(5) Uani 1 1 d . . . . .
C2 C 0.09016(13) 0.14595(10) -0.07958(10) 0.0369(5) Uani 1 1 d . . . . .
C20 C 0.33238(13) 0.00848(12) 0.22128(10) 0.0394(5) Uani 1 1 d . . . . .
C5 C 0.09952(16) 0.21365(12) -0.16141(11) 0.0475(6) Uani 1 1 d . . . . .
H5 H 0.079930 0.228971 -0.195961 0.057 Uiso 1 1 calc R U . . .
C8 C -0.24612(17) 0.18264(12) 0.14475(11) 0.0479(6) Uani 1 1 d . . . . .
C15 C 0.14838(13) -0.03200(10) 0.14881(10) 0.0360(4) Uani 1 1 d . . . . .
H15 H 0.110859 -0.061034 0.152236 0.043 Uiso 1 1 calc R U . . .
C14 C -0.08857(17) 0.06404(12) 0.06473(12) 0.0486(6) Uani 1 1 d . . . . .
C17 C 0.20791(13) -0.03261(10) 0.18797(10) 0.0360(4) Uani 1 1 d . . . . .
H17 H 0.209539 -0.061389 0.217223 0.043 Uiso 1 1 calc R U . . .
C18 C 0.25915(17) 0.05061(15) 0.13872(13) 0.0594(8) Uani 1 1 d . . . . .
H18 H 0.296331 0.079685 0.133801 0.071 Uiso 1 1 calc R U . . .
C11 C -0.12518(15) 0.13528(12) 0.14532(12) 0.0466(6) Uani 1 1 d . . . . .
H11 H -0.077794 0.129749 0.162263 0.056 Uiso 1 1 calc R U . . .
C6 C 0.19557(16) 0.21447(13) -0.08618(12) 0.0500(6) Uani 1 1 d . . . . .
H6 H 0.240393 0.229951 -0.071058 0.060 Uiso 1 1 calc R U . . .
C12 C -0.21553(19) 0.11163(14) 0.07200(13) 0.0584(7) Uani 1 1 d . . . . .
H12 H -0.229435 0.089727 0.039231 0.070 Uiso 1 1 calc R U . . .
C9 C -0.17615(17) 0.17471(12) 0.17044(12) 0.0484(6) Uani 1 1 d . . . . .
H9 H -0.163393 0.195525 0.204144 0.058 Uiso 1 1 calc R U . . .
C10 C -0.26673(19) 0.15090(15) 0.09624(14) 0.0608(8) Uani 1 1 d . . . . .
H10 H -0.314595 0.155800 0.079906 0.073 Uiso 1 1 calc R U . . .
C16 C 0.19808(18) 0.04847(15) 0.10115(14) 0.0622(9) Uani 1 1 d . . . . .
H16 H 0.195814 0.076183 0.070954 0.075 Uiso 1 1 calc R U . . .
C21 C 0.46644(19) 0.0261(3) 0.22958(15) 0.0998(18) Uani 1 1 d . . . . .
H21A H 0.468741 0.062974 0.251767 0.120 Uiso 1 1 calc R U . . .
H21B H 0.510946 0.024196 0.204812 0.120 Uiso 1 1 calc R U . . .


_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
Zn1 N1 2.0259(19) . ?
Zn1 O1 2.0300(17) . ?
Zn1 O2 2.0346(16) . ?
Zn1 O3 2.046(2) . ?
Zn1 O4 2.049(2) . ?
Zn1 Zn1 2.9657(5) 9 ?
O5 C7 1.385(3) 7_454 ?
O5 C8 1.394(3) . ?
N2 C20 1.391(3) . ?
N2 C21 1.438(4) . ?
N2 H2B 0.8200 . ?
O3 C14 1.260(4) . ?
C3 C5 1.389(3) . ?
C3 C2 1.393(3) . ?
C3 H3 0.9300 . ?
C13 C12 1.382(4) . ?
C13 C11 1.383(4) . ?
C13 C14 1.497(4) . ?
C4 C6 1.381(3) . ?
C4 C2 1.392(3) . ?
C4 H4 0.9300 . ?
O4 C14 1.250(4) 9 ?
C1 O2 1.255(3) . ?
C1 O1 1.257(3) 9 ?
C1 C2 1.498(3) . ?
N1 C16 1.329(3) . ?
N1 C15 1.343(3) . ?
C7 C5 1.383(4) . ?
C7 C6 1.394(4) . ?
C19 C18 1.383(4) . ?
C19 C17 1.387(3) . ?
C19 C20 1.466(3) . ?
C20 C20 1.371(5) 3 ?
C5 H5 0.9300 . ?
C8 C10 1.369(4) . ?
C8 C9 1.379(4) . ?
C15 C17 1.382(3) . ?
C15 H15 0.9300 . ?
C17 H17 0.9300 . ?
C18 C16 1.380(4) . ?
C18 H18 0.9300 . ?
C11 C9 1.384(4) . ?
C11 H11 0.9300 . ?
C6 H6 0.9300 . ?
C12 C10 1.377(4) . ?
C12 H12 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C16 H16 0.9300 . ?
C21 C21 1.495(10) 3 ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?

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
N1 Zn1 O1 100.33(7) . . ?
N1 Zn1 O2 100.43(7) . . ?
O1 Zn1 O2 159.22(7) . . ?
N1 Zn1 O3 101.92(9) . . ?
O1 Zn1 O3 87.80(9) . . ?
O2 Zn1 O3 88.86(8) . . ?
N1 Zn1 O4 99.01(9) . . ?
O1 Zn1 O4 88.15(9) . . ?
O2 Zn1 O4 87.67(9) . . ?
O3 Zn1 O4 159.06(9) . . ?
N1 Zn1 Zn1 172.61(6) . 9 ?
O1 Zn1 Zn1 81.63(5) . 9 ?
O2 Zn1 Zn1 77.65(5) . 9 ?
O3 Zn1 Zn1 85.23(6) . 9 ?
O4 Zn1 Zn1 73.86(7) . 9 ?
C7 O5 C8 118.6(2) 7_454 . ?
C20 N2 C21 116.3(2) . . ?
C20 N2 H2B 109.5 . . ?
C21 N2 H2B 112.8 . . ?
C14 O3 Zn1 120.22(19) . . ?
C5 C3 C2 120.6(2) . . ?
C5 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C12 C13 C11 118.5(3) . . ?
C12 C13 C14 119.2(3) . . ?
C11 C13 C14 122.3(3) . . ?
C6 C4 C2 121.0(2) . . ?
C6 C4 H4 119.5 . . ?
C2 C4 H4 119.5 . . ?
C14 O4 Zn1 135.5(2) 9 . ?
O2 C1 O1 125.7(2) . 9 ?
O2 C1 C2 117.2(2) . . ?
O1 C1 C2 117.1(2) 9 . ?
C16 N1 C15 117.1(2) . . ?
C16 N1 Zn1 121.81(17) . . ?
C15 N1 Zn1 120.88(16) . . ?
C1 O2 Zn1 129.73(16) . . ?
C5 C7 O5 115.9(2) . 7_554 ?
C5 C7 C6 121.1(2) . . ?
O5 C7 C6 122.9(2) 7_554 . ?
C1 O1 Zn1 124.77(15) 9 . ?
C18 C19 C17 116.6(2) . . ?
C18 C19 C20 120.9(2) . . ?
C17 C19 C20 122.3(2) . . ?
C4 C2 C3 119.1(2) . . ?
C4 C2 C1 119.9(2) . . ?
C3 C2 C1 120.9(2) . . ?
C20 C20 N2 120.64(14) 3 . ?
C20 C20 C19 124.81(14) 3 . ?
N2 C20 C19 114.5(2) . . ?
C7 C5 C3 119.2(2) . . ?
C7 C5 H5 120.4 . . ?
C3 C5 H5 120.4 . . ?
C10 C8 C9 121.2(3) . . ?
C10 C8 O5 121.1(3) . . ?
C9 C8 O5 117.6(3) . . ?
N1 C15 C17 122.8(2) . . ?
N1 C15 H15 118.6 . . ?
C17 C15 H15 118.6 . . ?
O4 C14 O3 125.1(3) 9 . ?
O4 C14 C13 117.1(3) 9 . ?
O3 C14 C13 117.8(3) . . ?
C15 C17 C19 120.0(2) . . ?
C15 C17 H17 120.0 . . ?
C19 C17 H17 120.0 . . ?
C16 C18 C19 120.2(2) . . ?
C16 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C13 C11 C9 120.8(3) . . ?
C13 C11 H11 119.6 . . ?
C9 C11 H11 119.6 . . ?
C4 C6 C7 119.0(2) . . ?
C4 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C10 C12 C13 121.4(3) . . ?
C10 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C8 C9 C11 119.0(3) . . ?
C8 C9 H9 120.5 . . ?
C11 C9 H9 120.5 . . ?
C8 C10 C12 119.0(3) . . ?
C8 C10 H10 120.5 . . ?
C12 C10 H10 120.5 . . ?
N1 C16 C18 123.2(2) . . ?
N1 C16 H16 118.4 . . ?
C18 C16 H16 118.4 . . ?
N2 C21 C21 110.7(3) . 3 ?
N2 C21 H21A 109.5 . . ?
C21 C21 H21A 109.5 3 . ?
N2 C21 H21B 109.5 . . ?
C21 C21 H21B 109.5 3 . ?
H21A C21 H21B 108.1 . . ?

_refine_diff_density_max         0.935
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.071




