# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_11_sq
_database_code_depnum_ccdc_archive 'CCDC 2024524'
loop_
_audit_author_name
_audit_author_address
'zhaohao li'
;luoyang normal university
China
;
_audit_update_record             
;
2020-09-18 deposited with the CCDC.	2020-12-15 downloaded from the CCDC.
;
_audit_creation_date             2019-10-25
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H13 N3 O6 S Zn'
_chemical_formula_sum            'C22 H15 N3 O9 S Zn'
_chemical_formula_weight         562.80
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.6890(10)
_cell_length_b                   19.055(3)
_cell_length_c                   16.139(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.027(4)
_cell_angle_gamma                90
_cell_volume                     2363.0(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2950
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.18
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   0.797
_shelx_estimated_absorpt_T_min   0.797
_exptl_absorpt_coefficient_mu    1.186
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15591
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.454
_diffrn_reflns_theta_min         1.654
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3338
_reflns_number_total             4369
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.733
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         4369
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²+0.6888P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0956
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Sof(C18B)=Sof(C19B)=Sof(H19B)=Sof(C20B)=Sof(H20B)=Sof(N3B)=Sof(C22B)=
 Sof(H22B)=Sof(C21B)=Sof(H21B)=1-FVAR(1)
 Sof(C18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=Sof(N3A)=Sof(C22A)=
 Sof(H22A)=Sof(C21A)=Sof(H21A)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C16(H16),
 C17(H17), C19A(H19A), C20A(H20A), C22A(H22A), C21A(H21A), C19B(H19B),
 C20B(H20B), C22B(H22B), C21B(H21B)
3.b Fitted hexagon refined as free rotating group:
 C18A(C19A,C20A,N3A,C22A,C21A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.1908(4) 0.31136(16) 0.98334(19) 0.0356(7) Uani 1 1 d . . . . .
C2 C 0.1809(4) 0.25708(15) 1.04949(19) 0.0341(7) Uani 1 1 d . . . . .
C3 C 0.2342(5) 0.18907(17) 1.0462(2) 0.0476(9) Uani 1 1 d . . . . .
H3 H 0.2870 0.1693 1.0008 0.057 Uiso 1 1 calc R . . . .
C4 C 0.2008(5) 0.15220(17) 1.1191(2) 0.0485(9) Uani 1 1 d . . . . .
H4 H 0.2291 0.1052 1.1270 0.058 Uiso 1 1 calc R . . . .
C5 C 0.1232(4) 0.19178(15) 1.17685(19) 0.0356(7) Uani 1 1 d . . . . .
C6 C 0.0660(4) 0.17109(16) 1.2599(2) 0.0398(8) Uani 1 1 d . . . . .
C7 C 0.7410(4) 0.4675(2) 0.8874(2) 0.0488(9) Uani 1 1 d . . . . .
C8 C 0.5659(4) 0.50430(16) 0.89021(18) 0.0320(7) Uani 1 1 d . . . . .
C9 C 0.4183(4) 0.46479(15) 0.89433(17) 0.0305(7) Uani 1 1 d . . . . .
H9 H 0.4290 0.4162 0.8918 0.037 Uiso 1 1 calc R . . . .
C10 C 0.2437(4) 0.56242(13) 0.90549(17) 0.0283(6) Uani 1 1 d . . . . .
H10 H 0.1348 0.5826 0.9117 0.034 Uiso 1 1 calc R . . . .
C11 C 0.3870(4) 0.60477(14) 0.90023(19) 0.0323(7) Uani 1 1 d . . . . .
C12 C 0.5513(4) 0.57643(16) 0.89252(19) 0.0378(7) Uani 1 1 d . . . . .
H12 H 0.6487 0.6051 0.8890 0.045 Uiso 1 1 calc R . . . .
C13 C 0.3096(4) 0.71221(16) 0.9695(2) 0.0427(8) Uani 1 1 d . . . . .
H13 H 0.2868 0.6860 1.0165 0.051 Uiso 1 1 calc R . . . .
C14 C 0.2868(5) 0.78384(16) 0.9697(2) 0.0475(9) Uani 1 1 d . . . . .
H14 H 0.2483 0.8059 1.0171 0.057 Uiso 1 1 calc R . . . .
C15 C 0.3207(5) 0.82328(17) 0.9001(2) 0.0495(9) Uani 1 1 d . . . . .
C16 C 0.3769(5) 0.78844(18) 0.8305(2) 0.0563(10) Uani 1 1 d . . . . .
H16 H 0.3994 0.8135 0.7826 0.068 Uiso 1 1 calc R . . . .
C17 C 0.3994(5) 0.71690(18) 0.8323(2) 0.0515(9) Uani 1 1 d . . . . .
H17 H 0.4386 0.6937 0.7858 0.062 Uiso 1 1 calc R . . . .
C18A C 0.315(2) 0.9002(4) 0.9031(6) 0.059(8) Uani 0.485(8) 1 d . . P A 1
C19A C 0.3546(14) 0.9375(3) 0.9754(5) 0.072(3) Uani 0.485(8) 1 d G . P A 1
H19A H 0.3784 0.9137 1.0248 0.086 Uiso 0.485(8) 1 calc R . P A 1
C20A C 0.3589(14) 1.0104(3) 0.9737(5) 0.090(4) Uani 0.485(8) 1 d G . P A 1
H20A H 0.3855 1.0354 1.0220 0.109 Uiso 0.485(8) 1 calc R . P A 1
N3A N 0.3234(17) 1.0460(4) 0.8999(6) 0.097(5) Uani 0.485(8) 1 d G . P A 1
C22A C 0.2836(19) 1.0087(7) 0.8277(5) 0.088(6) Uani 0.485(8) 1 d G . P A 1
H22A H 0.2598 1.0326 0.7783 0.106 Uiso 0.485(8) 1 calc R . P A 1
C21A C 0.279(2) 0.9358(7) 0.8293(5) 0.068(4) Uani 0.485(8) 1 d G . P A 1
H21A H 0.2527 0.9109 0.7810 0.082 Uiso 0.485(8) 1 calc R . P A 1
C18B C 0.288(3) 0.9021(6) 0.8966(9) 0.066(7) Uani 0.515(8) 1 d . . P A 2
C19B C 0.1817(17) 0.9329(4) 0.9532(8) 0.094(4) Uani 0.515(8) 1 d . . P A 2
H19B H 0.1262 0.9054 0.9919 0.113 Uiso 0.515(8) 1 calc R . P A 2
C20B C 0.158(2) 1.0052(5) 0.9523(9) 0.132(6) Uani 0.515(8) 1 d . . P A 2
H20B H 0.0939 1.0246 0.9943 0.158 Uiso 0.515(8) 1 calc R . P A 2
N3B N 0.217(4) 1.0468(6) 0.8987(9) 0.152(9) Uani 0.515(8) 1 d . . P A 2
C22B C 0.311(4) 1.0173(9) 0.8477(11) 0.148(12) Uani 0.515(8) 1 d . . P A 2
H22B H 0.3621 1.0467 0.8098 0.178 Uiso 0.515(8) 1 calc R . P A 2
C21B C 0.349(3) 0.9445(7) 0.8396(9) 0.096(7) Uani 0.515(8) 1 d . . P A 2
H21B H 0.4139 0.9276 0.7964 0.115 Uiso 0.515(8) 1 calc R . P A 2
N1 N 0.2583(3) 0.49221(11) 0.90180(14) 0.0282(5) Uani 1 1 d . . . . .
N2 N 0.3647(3) 0.68046(13) 0.90118(17) 0.0380(6) Uani 1 1 d . . . . .
O1 O 0.0805(3) 0.36113(10) 0.98782(13) 0.0380(5) Uani 1 1 d . . . . .
O2 O 0.3026(3) 0.30610(12) 0.93115(16) 0.0543(6) Uani 1 1 d . . . . .
O3 O -0.0129(4) 0.21285(13) 1.30266(16) 0.0631(7) Uani 1 1 d . . . . .
O4 O 0.1024(3) 0.10771(10) 1.28001(13) 0.0407(5) Uani 1 1 d . . . . .
O5 O 0.7432(4) 0.40280(16) 0.8878(2) 0.0830(10) Uani 1 1 d . . . . .
O6 O 0.8718(3) 0.50399(15) 0.8857(2) 0.0776(10) Uani 1 1 d . . . . .
S1 S 0.08934(11) 0.27605(4) 1.14186(5) 0.0389(2) Uani 1 1 d . . . . .
Zn1 Zn 0.04897(4) 0.42073(2) 0.89091(2) 0.02779(12) 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
C1 C2 1.490(4) . ?
C1 O1 1.276(4) . ?
C1 O2 1.229(4) . ?
C2 C3 1.361(4) . ?
C2 S1 1.709(3) . ?
C3 C4 1.401(5) . ?
C4 C5 1.354(5) . ?
C5 C6 1.479(4) . ?
C5 S1 1.719(3) . ?
C6 O3 1.228(4) . ?
C6 O4 1.279(4) . ?
C7 C8 1.520(4) . ?
C7 O5 1.234(5) . ?
C7 O6 1.223(4) . ?
C7 Zn1 2.529(3) 1_655 ?
C8 C9 1.365(4) . ?
C8 C12 1.380(4) . ?
C9 N1 1.346(3) . ?
C10 C11 1.371(4) . ?
C10 N1 1.344(3) . ?
C11 C12 1.383(4) . ?
C11 N2 1.453(4) . ?
C13 C14 1.376(4) . ?
C13 N2 1.340(4) . ?
C14 C15 1.384(5) . ?
C15 C16 1.387(5) . ?
C15 C18A 1.468(8) . ?
C15 C18B 1.523(12) . ?
C16 C17 1.374(4) . ?
C17 N2 1.346(4) . ?
C18A C19A 1.3900 . ?
C18A C21A 1.3900 . ?
C19A C20A 1.3900 . ?
C20A N3A 1.3900 . ?
N3A C22A 1.3900 . ?
C22A C21A 1.3900 . ?
C18B C19B 1.378(19) . ?
C18B C21B 1.322(15) . ?
C19B C20B 1.389(12) . ?
C20B N3B 1.269(18) . ?
N3B C22B 1.24(3) . ?
C22B C21B 1.426(17) . ?
N1 Zn1 2.111(2) . ?
O1 Zn1 1.941(2) . ?
O4 Zn1 1.928(2) 4_566 ?
O5 Zn1 2.375(3) 1_655 ?
O6 Zn1 2.091(3) 1_655 ?
Zn1 C7 2.529(3) 1_455 ?
Zn1 O4 1.928(2) 4_565 ?
Zn1 O5 2.375(3) 1_455 ?
Zn1 O6 2.091(3) 1_455 ?

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 C1 C2 115.1(3) . . ?
O2 C1 C2 119.3(3) . . ?
O2 C1 O1 125.6(3) . . ?
C1 C2 S1 120.7(2) . . ?
C3 C2 C1 127.6(3) . . ?
C3 C2 S1 111.7(2) . . ?
C2 C3 C4 112.3(3) . . ?
C5 C4 C3 113.4(3) . . ?
C4 C5 C6 128.9(3) . . ?
C4 C5 S1 111.1(2) . . ?
C6 C5 S1 120.0(2) . . ?
O3 C6 C5 120.3(3) . . ?
O3 C6 O4 125.3(3) . . ?
O4 C6 C5 114.3(3) . . ?
C8 C7 Zn1 172.6(3) . 1_655 ?
O5 C7 C8 118.2(3) . . ?
O5 C7 Zn1 68.6(2) . 1_655 ?
O6 C7 C8 118.0(4) . . ?
O6 C7 O5 123.8(3) . . ?
O6 C7 Zn1 55.32(19) . 1_655 ?
C9 C8 C7 119.1(3) . . ?
C9 C8 C12 118.7(3) . . ?
C12 C8 C7 122.2(3) . . ?
N1 C9 C8 123.6(3) . . ?
N1 C10 C11 121.0(3) . . ?
C10 C11 C12 121.0(3) . . ?
C10 C11 N2 119.2(3) . . ?
C12 C11 N2 119.8(3) . . ?
C8 C12 C11 117.8(3) . . ?
N2 C13 C14 119.6(3) . . ?
C13 C14 C15 120.6(3) . . ?
C14 C15 C16 118.1(3) . . ?
C14 C15 C18A 120.6(5) . . ?
C14 C15 C18B 122.0(6) . . ?
C16 C15 C18A 121.0(6) . . ?
C16 C15 C18B 119.8(6) . . ?
C17 C16 C15 120.0(4) . . ?
N2 C17 C16 120.0(3) . . ?
C19A C18A C15 122.2(7) . . ?
C19A C18A C21A 120.0 . . ?
C21A C18A C15 117.7(7) . . ?
C20A C19A C18A 120.0 . . ?
N3A C20A C19A 120.0 . . ?
C20A N3A C22A 120.0 . . ?
C21A C22A N3A 120.0 . . ?
C22A C21A C18A 120.0 . . ?
C19B C18B C15 119.8(11) . . ?
C21B C18B C15 124.4(12) . . ?
C21B C18B C19B 115.7(11) . . ?
C18B C19B C20B 119.7(12) . . ?
N3B C20B C19B 125.3(14) . . ?
C22B N3B C20B 113.3(12) . . ?
N3B C22B C21B 128.8(17) . . ?
C18B C21B C22B 116.8(14) . . ?
C9 N1 Zn1 116.02(18) . . ?
C10 N1 C9 117.9(2) . . ?
C10 N1 Zn1 125.54(19) . . ?
C13 N2 C11 119.9(3) . . ?
C13 N2 C17 121.7(3) . . ?
C17 N2 C11 118.5(3) . . ?
C1 O1 Zn1 116.97(19) . . ?
C6 O4 Zn1 116.7(2) . 4_566 ?
C7 O5 Zn1 82.5(2) . 1_655 ?
C7 O6 Zn1 95.9(2) . 1_655 ?
C2 S1 C5 91.53(15) . . ?
N1 Zn1 C7 119.00(11) . 1_455 ?
N1 Zn1 O5 147.78(9) . 1_455 ?
O1 Zn1 C7 108.33(11) . 1_455 ?
O1 Zn1 N1 103.72(9) . . ?
O1 Zn1 O5 91.64(9) . 1_455 ?
O1 Zn1 O6 122.63(11) . 1_455 ?
O4 Zn1 C7 107.98(10) 4_565 1_455 ?
O4 Zn1 N1 94.11(9) 4_565 . ?
O4 Zn1 O1 123.97(9) 4_565 . ?
O4 Zn1 O5 100.55(11) 4_565 1_455 ?
O4 Zn1 O6 109.61(11) 4_565 1_455 ?
O5 Zn1 C7 28.92(11) 1_455 1_455 ?
O6 Zn1 C7 28.76(12) 1_455 1_455 ?
O6 Zn1 N1 90.43(10) 1_455 . ?
O6 Zn1 O5 57.67(10) 1_455 1_455 ?

_platon_squeeze_details          ?
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
_platon_squeeze_void_content
1 0.002 0.879 0.178 100 28 ' '
2 -0.002 0.379 0.322 99 28 ' '
3 0.002 0.621 0.678 100 29 ' '
4 -0.002 0.121 0.822 100 29 ' '

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
