# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_511-2
_database_code_depnum_ccdc_archive 'CCDC 2083695'
loop_
_audit_author_name
_audit_author_address
'ZHAOHAO LI'
;Luoyang Normal University
China
;
_audit_update_record             
;
2021-05-14 deposited with the CCDC.	2021-07-30 downloaded from the CCDC.
;
_audit_creation_date             2021-05-14
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H14 N2 O6 S Zn'
_chemical_formula_sum            'C23 H14 N2 O6 S Zn'
_chemical_formula_weight         511.79
_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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   10.146(2)
_cell_length_b                   13.915(2)
_cell_length_c                   14.641(12)
_cell_angle_alpha                90
_cell_angle_beta                 96.29(7)
_cell_angle_gamma                90
_cell_volume                     2054.5(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3644
_cell_measurement_temperature    290.6(3)
_cell_measurement_theta_max      27.2950
_cell_measurement_theta_min      4.0380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.343
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28954
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.839
_diffrn_reflns_theta_min         3.159
_diffrn_ambient_temperature      290.6(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     16.00  56.00   1.00   15.00    --  -13.49  38.00 -90.00   40
  2  ω    -62.00 -36.00   1.00   15.00    --  -13.49-178.00  60.00   26
  3  ω    -14.00  25.00   1.00   15.00    --  -13.49 -99.00-180.00   39
  4  ω     -2.00  78.00   1.00   15.00    --   14.89  57.00   0.00   80
  5  ω    -15.00  85.00   1.00   15.00    --   14.89  19.00 -60.00  100
  6  ω     -2.00  81.00   1.00   15.00    --   14.89  57.00  60.00   83
  7  ω    -17.00  54.00   1.00   15.00    --   14.89 -99.00 120.00   71
  8  ω    -17.00  54.00   1.00   15.00    --   14.89 -99.00-120.00   71
  9  ω    -20.00  54.00   1.00   15.00    --   14.89 -99.00   0.00   74
 10  ω     -4.00  84.00   1.00   15.00    --   14.89  38.00-180.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0386098000
_diffrn_orient_matrix_UB_12      -0.0319238000
_diffrn_orient_matrix_UB_13      0.0238284000
_diffrn_orient_matrix_UB_21      -0.0548359000
_diffrn_orient_matrix_UB_22      0.0082086000
_diffrn_orient_matrix_UB_23      -0.0334610000
_diffrn_orient_matrix_UB_31      0.0200658000
_diffrn_orient_matrix_UB_32      -0.0385231000
_diffrn_orient_matrix_UB_33      -0.0271227000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3949
_reflns_number_total             4674
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.363
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4674
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0360
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0277P)²+1.5619P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0797
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23)
;
_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
Zn1 Zn 0.90664(2) 0.54542(2) 0.29809(2) 0.02658(9) Uani 1 1 d . . . . .
S1 S 1.25329(6) 0.32670(4) 0.24539(4) 0.03038(14) Uani 1 1 d . . . . .
O1 O 1.03656(16) 0.45676(12) 0.26553(12) 0.0347(4) Uani 1 1 d . . . . .
O2 O 0.96428(19) 0.48201(15) 0.11309(13) 0.0528(5) Uani 1 1 d . . . . .
O3 O 1.46953(18) 0.18674(14) 0.28756(12) 0.0453(5) Uani 1 1 d . . . . .
O4 O 1.50420(16) 0.16333(11) 0.14329(12) 0.0346(4) Uani 1 1 d . . . . .
O5 O 0.83880(16) 0.50053(12) 0.41098(12) 0.0383(4) Uani 1 1 d . . . . .
O6 O 0.73072(19) 0.38753(13) 0.32073(13) 0.0452(5) Uani 1 1 d . . . . .
N1 N 0.37990(18) 0.27237(13) 0.50142(13) 0.0277(4) Uani 1 1 d . . . . .
N2 N -0.23334(18) 0.08657(14) 0.28765(14) 0.0308(4) Uani 1 1 d . . . . .
C1 C 1.0427(2) 0.44888(16) 0.17841(17) 0.0294(5) Uani 1 1 d . . . . .
C2 C 1.1593(2) 0.39240(15) 0.15838(15) 0.0259(5) Uani 1 1 d . . . . .
C3 C 1.2012(2) 0.38068(16) 0.07457(16) 0.0288(5) Uani 1 1 d . . . . .
H3 H 1.1646 0.4106 0.0209 0.035 Uiso 1 1 calc R . . . .
C4 C 1.3089(2) 0.31621(16) 0.08089(16) 0.0299(5) Uani 1 1 d . . . . .
H4 H 1.3509 0.2987 0.0301 0.036 Uiso 1 1 calc R . . . .
C5 C 1.3478(2) 0.28061(15) 0.16850(16) 0.0267(5) Uani 1 1 d . . . . .
C6 C 1.4480(2) 0.20554(16) 0.20360(17) 0.0283(5) Uani 1 1 d . . . . .
C7 C 0.7559(2) 0.43129(16) 0.39520(18) 0.0307(5) Uani 1 1 d . . . . .
C8 C 0.6833(2) 0.40637(16) 0.47438(16) 0.0281(5) Uani 1 1 d . . . . .
C9 C 0.7197(2) 0.44401(17) 0.56339(17) 0.0345(6) Uani 1 1 d . . . . .
H9 H 0.7932 0.4840 0.5739 0.041 Uiso 1 1 calc R . . . .
C10 C 0.6484(3) 0.4223(2) 0.63296(18) 0.0426(6) Uani 1 1 d . . . . .
H10 H 0.6728 0.4456 0.6919 0.051 Uiso 1 1 calc R . . . .
C11 C 0.5377(3) 0.36407(19) 0.61432(17) 0.0384(6) Uani 1 1 d . . . . .
H11 H 0.4861 0.3493 0.6611 0.046 Uiso 1 1 calc R . . . .
C12 C 0.5027(2) 0.32724(16) 0.52563(16) 0.0281(5) Uani 1 1 d . . . . .
C13 C 0.5737(2) 0.34624(16) 0.45525(16) 0.0275(5) Uani 1 1 d . . . . .
H13 H 0.5508 0.3207 0.3970 0.033 Uiso 1 1 calc R . . . .
C14 C 0.2652(2) 0.31552(18) 0.51328(17) 0.0344(6) Uani 1 1 d . . . . .
H14 H 0.2660 0.3735 0.5450 0.041 Uiso 1 1 calc R . . . .
C15 C 0.1454(2) 0.27501(18) 0.47902(17) 0.0356(6) Uani 1 1 d . . . . .
H15 H 0.0669 0.3063 0.4880 0.043 Uiso 1 1 calc R . . . .
C16 C 0.1401(2) 0.18838(16) 0.43133(15) 0.0275(5) Uani 1 1 d . . . . .
C17 C 0.2592(2) 0.14264(16) 0.42601(16) 0.0295(5) Uani 1 1 d . . . . .
H17 H 0.2605 0.0822 0.3990 0.035 Uiso 1 1 calc R . . . .
C18 C 0.3780(2) 0.18603(16) 0.46072(16) 0.0292(5) Uani 1 1 d . . . . .
H18 H 0.4576 0.1544 0.4556 0.035 Uiso 1 1 calc R . . . .
C19 C 0.0110(2) 0.15096(16) 0.38288(16) 0.0289(5) Uani 1 1 d . . . . .
C20 C -0.0837(2) 0.21429(17) 0.33904(18) 0.0329(5) Uani 1 1 d . . . . .
H20 H -0.0670 0.2800 0.3406 0.039 Uiso 1 1 calc R . . . .
C21 C -0.2035(2) 0.17964(17) 0.29272(18) 0.0334(5) Uani 1 1 d . . . . .
H21 H -0.2640 0.2236 0.2646 0.040 Uiso 1 1 calc R . . . .
C22 C -0.1424(2) 0.02567(18) 0.33165(19) 0.0395(6) Uani 1 1 d . . . . .
H22 H -0.1622 -0.0396 0.3307 0.047 Uiso 1 1 calc R . . . .
C23 C -0.0202(2) 0.05487(18) 0.37848(19) 0.0376(6) Uani 1 1 d . . . . .
H23 H 0.0388 0.0096 0.4061 0.045 Uiso 1 1 calc R . . . .


_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 O1 1.9037(16) . ?
Zn1 O4 2.0191(17) 2_755 ?
Zn1 O5 1.961(2) . ?
Zn1 N2 2.124(2) 2 ?
S1 C2 1.761(3) . ?
S1 C5 1.684(2) . ?
O1 C1 1.289(3) . ?
O2 C1 1.262(3) . ?
O3 C6 1.252(3) . ?
O4 Zn1 2.0191(17) 2_745 ?
O4 C6 1.249(3) . ?
O5 C7 1.283(3) . ?
O6 C7 1.250(3) . ?
N1 C12 1.471(3) . ?
N1 C14 1.337(3) . ?
N1 C18 1.340(3) . ?
N2 Zn1 2.124(2) 2_545 ?
N2 C21 1.330(3) . ?
N2 C22 1.362(3) . ?
C1 C2 1.476(3) . ?
C2 C3 1.352(3) . ?
C3 C4 1.409(3) . ?
C4 C5 1.391(3) . ?
C5 C6 1.508(3) . ?
C7 C8 1.481(3) . ?
C8 C9 1.415(4) . ?
C8 C13 1.396(3) . ?
C9 C10 1.346(4) . ?
C10 C11 1.387(3) . ?
C11 C12 1.405(4) . ?
C12 C13 1.346(3) . ?
C14 C15 1.383(3) . ?
C15 C16 1.391(3) . ?
C16 C17 1.376(3) . ?
C16 C19 1.512(3) . ?
C17 C18 1.393(3) . ?
C19 C20 1.406(3) . ?
C19 C23 1.374(3) . ?
C20 C21 1.411(3) . ?
C22 C23 1.409(4) . ?

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 Zn1 O4 110.04(7) . 2_755 ?
O1 Zn1 O5 108.74(8) . . ?
O1 Zn1 N2 125.29(8) . 2 ?
O4 Zn1 N2 109.60(8) 2_755 2 ?
O5 Zn1 O4 94.75(8) . 2_755 ?
O5 Zn1 N2 103.87(9) . 2 ?
C5 S1 C2 90.98(12) . . ?
C1 O1 Zn1 114.39(15) . . ?
C6 O4 Zn1 107.43(15) . 2_745 ?
C7 O5 Zn1 111.78(17) . . ?
C14 N1 C12 117.50(19) . . ?
C14 N1 C18 119.3(2) . . ?
C18 N1 C12 122.88(19) . . ?
C21 N2 Zn1 117.65(16) . 2_545 ?
C21 N2 C22 116.2(2) . . ?
C22 N2 Zn1 125.88(16) . 2_545 ?
O1 C1 C2 111.6(2) . . ?
O2 C1 O1 128.6(2) . . ?
O2 C1 C2 119.8(2) . . ?
C1 C2 S1 120.99(18) . . ?
C3 C2 S1 113.24(17) . . ?
C3 C2 C1 125.7(2) . . ?
C2 C3 C4 109.6(2) . . ?
C5 C4 C3 115.3(2) . . ?
C4 C5 S1 110.84(17) . . ?
C4 C5 C6 132.3(2) . . ?
C6 C5 S1 116.62(17) . . ?
O3 C6 C5 121.2(2) . . ?
O4 C6 O3 123.5(2) . . ?
O4 C6 C5 115.3(2) . . ?
O5 C7 C8 114.0(2) . . ?
O6 C7 O5 126.1(2) . . ?
O6 C7 C8 119.8(2) . . ?
C9 C8 C7 122.2(2) . . ?
C13 C8 C7 115.9(2) . . ?
C13 C8 C9 121.9(2) . . ?
C10 C9 C8 120.4(2) . . ?
C9 C10 C11 118.2(2) . . ?
C10 C11 C12 120.8(2) . . ?
C11 C12 N1 122.3(2) . . ?
C13 C12 N1 115.3(2) . . ?
C13 C12 C11 122.3(2) . . ?
C12 C13 C8 116.4(2) . . ?
N1 C14 C15 120.8(2) . . ?
C14 C15 C16 121.3(2) . . ?
C15 C16 C19 121.2(2) . . ?
C17 C16 C15 116.3(2) . . ?
C17 C16 C19 122.4(2) . . ?
C16 C17 C18 120.6(2) . . ?
N1 C18 C17 121.4(2) . . ?
C20 C19 C16 120.8(2) . . ?
C23 C19 C16 122.7(2) . . ?
C23 C19 C20 116.5(2) . . ?
C19 C20 C21 121.0(2) . . ?
N2 C21 C20 122.6(2) . . ?
N2 C22 C23 124.4(2) . . ?
C19 C23 C22 119.3(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.636
_oxdiff_exptl_absorpt_empirical_full_min 0.304
