# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_p151130b
_database_code_depnum_ccdc_archive 'CCDC 1889630'
_audit_update_record             
;
2019-01-09 deposited with the CCDC.	2019-03-07 downloaded from the CCDC.
;
_audit_creation_date             2018-12-06
_audit_creation_method           
;
Olex2 1.2
(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         'C24 H14 O22 S4 Zn4'
_chemical_formula_sum            'C24 H14 O22 S4 Zn4'
_chemical_formula_weight         1044.07
_chemical_melting_point          ?
_chemical_oxdiff_formula         'zn1 c1 o1 s1'
_chemical_oxdiff_usercomment     Zn-1
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'
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           10
_space_group_name_H-M_alt        'P 1 2/m 1'
_space_group_name_Hall           '-P 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'-x, -y, -z'
'x, -y, z'

_cell_length_a                   14.3588(12)
_cell_length_b                   15.763(2)
_cell_length_c                   15.6688(16)
_cell_angle_alpha                90
_cell_angle_beta                 103.497(9)
_cell_angle_gamma                90
_cell_volume                     3448.6(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2914
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.2480
_cell_measurement_theta_min      3.1830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.541
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.005
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1036
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.00
_diffrn_reflns_av_unetI/netI     0.1621
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            6308
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         2.968
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2116
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     38.00  93.00   1.00   52.10    --   18.94 178.00 -90.00   55
  2  ω    -30.00   6.00   1.00   52.10    --   18.94 -57.00 -30.00   36
  3  ω    -40.00  50.00   1.00   52.10    --  -19.25  57.00  60.00   90
  4  ω    -48.00   5.00   1.00   52.10    --  -19.25  77.00 -90.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0498450000
_diffrn_orient_matrix_UB_12      0.0081200000
_diffrn_orient_matrix_UB_13      0.0138761000
_diffrn_orient_matrix_UB_21      -0.0067864000
_diffrn_orient_matrix_UB_22      0.0403458000
_diffrn_orient_matrix_UB_23      -0.0203956000
_diffrn_orient_matrix_UB_31      -0.0070962000
_diffrn_orient_matrix_UB_32      0.0180667000
_diffrn_orient_matrix_UB_33      0.0395200000
_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                2520
_reflns_number_total             6308
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.391
_refine_diff_density_min         -1.197
_refine_diff_density_rms         0.193
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         6308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1874
_refine_ls_R_factor_gt           0.1236
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3601
_refine_ls_wR_factor_ref         0.4000
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: H00A(0.5) H00B(0.5) H2AA(0.5) H2AB(0.5) O1AA(0.5) H1AA(0.5)
 H1AB(0.5) O(0.5)
3.a Rotating group:
 O008(H00A,H00B), O2AA(H2AA,H2AB), O1AA(H1AA,H1AB)
3.b Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00S(H00S), C00U(H00U), C015(H015)
;
_atom_sites_solution_hydrogens   mixed
_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
Zn01 Zn 0.86139(10) 0.0000 -0.13807(10) 0.0345(5) Uani 1 2 d S T P . .
Zn02 Zn 0.63711(14) 0.5000 0.21869(13) 0.0657(8) Uani 1 2 d S T P . .
Zn03 Zn 0.86087(10) 0.5000 0.36267(10) 0.0333(5) Uani 1 2 d S T P . .
Zn04 Zn 0.63756(10) 0.0000 -0.28122(10) 0.0347(5) Uani 1 2 d S T P . .
S005 S 0.74418(19) 0.2656(2) 0.0717(2) 0.0540(9) Uani 1 1 d . . . . .
S006 S 0.74312(18) 0.2412(2) -0.42702(18) 0.0476(8) Uani 1 1 d . . . . .
O007 O 0.7004(7) 0.5000 0.3490(7) 0.053(3) Uani 1 2 d S T P . .
O008 O 1.0096(7) 0.5000 0.3929(10) 0.064(3) Uani 1 2 d S T P . .
H00A H 1.0311 0.4793 0.3495 0.096 Uiso 0.5 1 d GR . . . .
H00B H 1.0328 0.4651 0.4360 0.096 Uiso 0.5 1 d GR . . . .
O009 O 0.8544(5) 0.0958(6) -0.2302(6) 0.063(2) Uani 1 1 d . . . . .
O00A O 0.7096(5) 0.1049(6) -0.3169(5) 0.062(2) Uani 1 1 d . . . . .
O00B O 0.8701(5) 0.4129(5) -0.5382(5) 0.059(2) Uani 1 1 d . . . . .
C00C C 0.7876(8) 0.1276(7) -0.2939(7) 0.041(3) Uani 1 1 d . . . . .
O00E O 0.7201(5) 0.1438(7) -0.0587(6) 0.076(3) Uani 1 1 d . . . . .
O00F O 0.8740(5) 0.0970(5) -0.0414(5) 0.054(2) Uani 1 1 d . . . . .
C00G C 0.9161(7) 0.2883(7) -0.3996(7) 0.049(3) Uani 1 1 d . . . . .
H00G H 0.9738 0.3098 -0.4076 0.059 Uiso 1 1 calc R . . . .
O00H O 0.6994(6) 0.0000 -0.1512(6) 0.047(3) Uani 1 2 d S T P . .
O00I O 0.7189(5) 0.3786(5) -0.5587(5) 0.054(2) Uani 1 1 d . . . . .
O00J O 0.8536(6) 0.4086(6) 0.2669(6) 0.076(3) Uani 1 1 d . . . . .
C00K C 0.8036(6) 0.3687(7) -0.5205(7) 0.037(2) Uani 1 1 d . . . . .
O00L O 0.7072(5) 0.4086(5) 0.1789(5) 0.050(2) Uani 1 1 d . . . . .
C00M C 0.8311(6) 0.3126(7) -0.4501(7) 0.041(3) Uani 1 1 d . . . . .
C00P C 0.8257(7) 0.3206(7) 0.1496(7) 0.047(3) Uani 1 1 d . . . . .
C00Q C 0.8192(8) 0.1936(9) -0.3416(8) 0.064(4) Uani 1 1 d . . . . .
C00S C 0.9123(9) 0.2317(10) -0.3377(9) 0.070(4) Uani 1 1 d . . . . .
H00S H 0.9661 0.2174 -0.2943 0.084 Uiso 1 1 calc R . . . .
C00T C 0.8053(7) 0.1452(8) -0.0257(6) 0.049(3) Uani 1 1 d . . . . .
C00U C 0.9185(8) 0.3001(8) 0.1495(8) 0.054(3) Uani 1 1 d . . . . .
H00U H 0.9714 0.3236 0.1880 0.065 Uiso 1 1 calc R . . . .
C00V C 0.8349(8) 0.2150(8) 0.0397(7) 0.051(3) Uani 1 1 d . . . . .
C010 C 0.8001(8) 0.3869(8) 0.2026(7) 0.045(3) Uani 1 1 d . . . . .
C015 C 0.9250(8) 0.2421(9) 0.0875(9) 0.065(4) Uani 1 1 d . . . . .
H015 H 0.9826 0.2224 0.0777 0.078 Uiso 1 1 calc R . . . .
O2AA O 1.0070(6) 0.0000 -0.1145(6) 0.046(3) Uani 1 2 d S T P . .
H2AA H 1.0825 -0.0538 -0.1049 0.069 Uiso 0.5 1 d GR . . . .
H2AB H 1.0862 0.0183 -0.0496 0.069 Uiso 0.5 1 d GR . . . .
O1AA O 0.5356(10) 0.0935(11) -0.2479(8) 0.058(4) Uani 0.5 1 d . . . . .
H1AA H 0.5498 0.1585 -0.2199 0.088 Uiso 0.5 1 d GR . . . .
H1AB H 0.4566 0.0884 -0.2540 0.088 Uiso 0.5 1 d GR . . . .
O O 0.5238(8) 0.4763(8) 0.1357(8) 0.046(5) Uani 0.5 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
Zn01 O009 2.075(9) 4 ?
Zn01 O009 2.075(9) . ?
Zn01 O00F 2.130(8) 4 ?
Zn01 O00F 2.130(8) . ?
Zn01 O00H 2.287(9) . ?
Zn01 O2AA 2.037(9) . ?
Zn02 O007 2.032(10) . ?
Zn02 O00L 1.942(8) 4_565 ?
Zn02 O00L 1.942(8) . ?
Zn02 O 1.869(12) . ?
Zn02 O 1.869(12) 4_565 ?
Zn03 O007 2.263(10) . ?
Zn03 O008 2.077(9) . ?
Zn03 O00B 2.054(7) 1_556 ?
Zn03 O00B 2.054(7) 4_566 ?
Zn03 O00J 2.066(8) . ?
Zn03 O00J 2.066(8) 4_565 ?
Zn04 O00A 2.095(9) . ?
Zn04 O00A 2.095(9) 4 ?
Zn04 O00H 2.023(9) . ?
Zn04 O1AA 2.224(14) . ?
Zn04 O1AA 2.224(14) 4 ?
S005 C00P 1.716(11) . ?
S005 C00V 1.700(11) . ?
S006 C00M 1.791(10) . ?
S006 C00Q 1.693(12) . ?
O009 C00C 1.313(13) . ?
O00A C00C 1.150(12) . ?
O00B Zn03 2.054(7) 1_554 ?
O00B C00K 1.264(11) . ?
C00C C00Q 1.415(16) . ?
O00E C00T 1.212(11) . ?
O00F C00T 1.313(13) . ?
C00G C00M 1.345(14) . ?
C00G C00S 1.329(16) . ?
O00I C00K 1.235(10) . ?
O00J C010 1.166(12) . ?
C00K C00M 1.397(15) . ?
O00L C010 1.343(13) . ?
C00P C00U 1.372(15) . ?
C00P C010 1.436(16) . ?
C00Q C00S 1.454(17) . ?
C00T C00V 1.496(16) . ?
C00U C015 1.353(17) . ?
C00V C015 1.401(16) . ?
O O 0.75(3) 4_565 ?

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
O009 Zn01 O009 93.4(5) 4 . ?
O009 Zn01 O00F 177.8(3) . 4 ?
O009 Zn01 O00F 87.4(3) . . ?
O009 Zn01 O00F 87.4(3) 4 4 ?
O009 Zn01 O00F 177.8(3) 4 . ?
O009 Zn01 O00H 93.1(3) 4 . ?
O009 Zn01 O00H 93.1(3) . . ?
O00F Zn01 O00F 91.8(5) 4 . ?
O00F Zn01 O00H 88.9(2) . . ?
O00F Zn01 O00H 88.9(2) 4 . ?
O2AA Zn01 O009 90.4(3) . 4 ?
O2AA Zn01 O009 90.4(3) . . ?
O2AA Zn01 O00F 87.6(3) . . ?
O2AA Zn01 O00F 87.6(3) . 4 ?
O2AA Zn01 O00H 174.9(4) . . ?
O00L Zn02 O007 100.3(3) . . ?
O00L Zn02 O007 100.3(3) 4_565 . ?
O00L Zn02 O00L 95.8(4) . 4_565 ?
O Zn02 O007 144.3(5) . . ?
O Zn02 O007 144.3(5) 4_565 . ?
O Zn02 O00L 110.9(4) 4_565 . ?
O Zn02 O00L 93.5(4) 4_565 4_565 ?
O Zn02 O00L 93.5(4) . . ?
O Zn02 O00L 110.9(5) . 4_565 ?
O Zn02 O 23.1(8) 4_565 . ?
O008 Zn03 O007 172.5(5) . . ?
O00B Zn03 O007 87.5(3) 1_556 . ?
O00B Zn03 O007 87.5(3) 4_566 . ?
O00B Zn03 O008 86.9(4) 1_556 . ?
O00B Zn03 O008 86.9(4) 4_566 . ?
O00B Zn03 O00B 83.9(5) 4_566 1_556 ?
O00B Zn03 O00J 177.6(4) 1_556 4_565 ?
O00B Zn03 O00J 93.8(4) 4_566 4_565 ?
O00B Zn03 O00J 177.6(4) 4_566 . ?
O00B Zn03 O00J 93.8(4) 1_556 . ?
O00J Zn03 O007 93.1(3) . . ?
O00J Zn03 O007 93.1(3) 4_565 . ?
O00J Zn03 O008 92.3(4) 4_565 . ?
O00J Zn03 O008 92.3(4) . . ?
O00J Zn03 O00J 88.5(6) . 4_565 ?
O00A Zn04 O00A 104.3(5) 4 . ?
O00A Zn04 O1AA 86.2(5) . . ?
O00A Zn04 O1AA 168.3(5) 4 . ?
O00A Zn04 O1AA 168.3(5) . 4 ?
O00A Zn04 O1AA 86.2(5) 4 4 ?
O00H Zn04 O00A 98.1(3) . . ?
O00H Zn04 O00A 98.1(3) . 4 ?
O00H Zn04 O1AA 85.5(4) . 4 ?
O00H Zn04 O1AA 85.5(4) . . ?
O1AA Zn04 O1AA 83.0(9) 4 . ?
C00V S005 C00P 90.2(5) . . ?
C00Q S006 C00M 94.8(5) . . ?
Zn02 O007 Zn03 107.6(4) . . ?
C00C O009 Zn01 135.7(7) . . ?
C00C O00A Zn04 131.9(8) . . ?
C00K O00B Zn03 128.0(7) . 1_554 ?
O009 C00C C00Q 114.5(10) . . ?
O00A C00C O009 127.2(11) . . ?
O00A C00C C00Q 118.2(11) . . ?
C00T O00F Zn01 127.3(6) . . ?
C00S C00G C00M 115.8(10) . . ?
Zn04 O00H Zn01 106.8(4) . . ?
C010 O00J Zn03 138.0(9) . . ?
O00B C00K C00M 115.7(8) . . ?
O00I C00K O00B 122.2(10) . . ?
O00I C00K C00M 121.9(9) . . ?
C010 O00L Zn02 131.0(7) . . ?
C00G C00M S006 106.8(8) . . ?
C00G C00M C00K 134.0(9) . . ?
C00K C00M S006 118.4(7) . . ?
C00U C00P S005 112.4(9) . . ?
C00U C00P C010 123.6(10) . . ?
C010 C00P S005 123.7(8) . . ?
C00C C00Q S006 121.0(9) . . ?
C00C C00Q C00S 133.4(12) . . ?
C00S C00Q S006 105.5(10) . . ?
C00G C00S C00Q 116.1(11) . . ?
O00E C00T O00F 129.6(11) . . ?
O00E C00T C00V 113.8(10) . . ?
O00F C00T C00V 116.6(9) . . ?
C015 C00U C00P 113.0(11) . . ?
C00T C00V S005 115.6(8) . . ?
C015 C00V S005 112.0(10) . . ?
C015 C00V C00T 132.0(11) . . ?
O00J C010 O00L 125.2(11) . . ?
O00J C010 C00P 120.4(11) . . ?
O00L C010 C00P 113.4(9) . . ?
C00U C015 C00V 112.4(11) . . ?
O O Zn02 78.5(4) 4_565 . ?

_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 2.091
_oxdiff_exptl_absorpt_empirical_full_min 0.455
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 -0.062 0.399 -0.025 1961 676 ' '
_platon_squeeze_details          ?
####################################################################### 
# 
# 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_mo_161128b_0m
_database_code_depnum_ccdc_archive 'CCDC 1889631'
_audit_update_record             
;
2019-01-09 deposited with the CCDC.	2019-03-07 downloaded from the CCDC.
;
_audit_creation_date             2018-12-05
_audit_creation_method           
;
Olex2 1.2
(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 H15 N2 O11 S2 Zn2'
_chemical_formula_sum            'C22 H15 N2 O11 S2 Zn2'
_chemical_formula_weight         678.22
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.1191(10)
_cell_length_b                   11.1367(10)
_cell_length_c                   15.4541(14)
_cell_angle_alpha                87.029(3)
_cell_angle_beta                 86.265(3)
_cell_angle_gamma                84.741(3)
_cell_volume                     1899.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9792
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      3.03
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.415
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0595 before and 0.0525 after correction.
The Ratio of minimum to maximum transmission is 0.8906.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             682
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27064
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.005
_diffrn_reflns_theta_max         25.005
_diffrn_reflns_theta_min         2.906
_diffrn_ambient_temperature      290.08
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6200
_reflns_number_total             6624
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         4.108
_refine_diff_density_min         -1.185
_refine_diff_density_rms         0.174
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         6624
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0874
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0918P)²+23.8315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2294
_refine_ls_wR_factor_ref         0.2310
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C18) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3.a Rotating group:
 O9(H9A,H9B), O11(H11A,H11B)
3.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C25(H25), C29(H29), C31(H31), C37(H37), C38(H38), C40(H40),
 C44(H44), C53(H53), C54(H54), C57(H57)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.87175(7) 0.10424(7) 0.12580(5) 0.0177(2) Uani 1 1 d . . . . .
Zn2 Zn 0.74287(8) 0.19883(8) 0.33424(5) 0.0244(3) Uani 1 1 d . . . . .
S3 S 0.36149(14) 0.12179(18) 0.22840(11) 0.0223(4) Uani 1 1 d . . . . .
S4 S 0.83805(18) 0.60091(14) 0.23220(11) 0.0225(4) Uani 1 1 d . . . . .
O1 O 0.8722(4) 0.0820(4) 0.2659(3) 0.0130(9) Uani 1 1 d . . . . .
O2 O 0.8857(5) 0.9147(4) 0.1166(3) 0.0256(11) Uani 1 1 d . . . . .
O3 O 0.6885(4) 0.1069(6) 0.1228(3) 0.0294(13) Uani 1 1 d . . . . .
O4 O 0.0612(4) 0.0943(5) 0.1170(3) 0.0275(12) Uani 1 1 d . . . . .
O0AA O 0.8036(5) 0.3425(4) 0.2630(3) 0.0278(12) Uani 1 1 d . . . . .
O7 O 0.6117(4) 0.1593(5) 0.2560(3) 0.0285(12) Uani 1 1 d . . . . .
O8 O 0.8639(6) 0.2887(4) 0.1280(4) 0.0337(13) Uani 1 1 d . . . . .
O9 O 0.8873(5) 0.1138(5) -0.0104(3) 0.0268(12) Uani 1 1 d . . . . .
H9A H 0.8199 0.1451 -0.0310 0.040 Uiso 1 1 d GR . . . .
H9B H 0.9038 0.0423 -0.0305 0.040 Uiso 1 1 d GR . . . .
O10 O 0.0996(5) 0.1109(6) 0.2568(3) 0.0343(14) Uani 1 1 d . . . . .
O11 O 0.6078(6) 0.3139(6) 0.3979(4) 0.0433(16) Uani 1 1 d . . . . .
H11A H 0.6397 0.3564 0.4350 0.065 Uiso 1 1 d GR . . . .
H11B H 0.5536 0.2724 0.4264 0.065 Uiso 1 1 d GR . . . .
O12 O 0.8425(6) 0.8586(5) 0.2557(3) 0.0338(14) Uani 1 1 d . . . . .
C14 C 0.8637(7) 0.8380(6) 0.1780(4) 0.0194(14) Uani 1 1 d . . . . .
C15 C 0.8402(6) 0.3616(6) 0.1844(5) 0.0206(15) Uani 1 1 d . . . . .
C16 C 0.8658(6) 0.7103(6) 0.1527(5) 0.0197(14) Uani 1 1 d . . . . .
C17 C 0.8544(6) 0.4903(6) 0.1573(5) 0.0201(14) Uani 1 1 d . . . . .
C18 C 0.4794(6) 0.1199(6) 0.1513(5) 0.0186(14) Uani 1 1 d . U . . .
C19 C 0.1298(6) 0.1038(6) 0.1772(5) 0.0191(14) Uani 1 1 d . . . . .
C20 C 0.6048(6) 0.1295(6) 0.1783(5) 0.0197(14) Uani 1 1 d . . . . .
C21 C 0.2611(6) 0.1085(7) 0.1508(5) 0.0205(14) Uani 1 1 d . . . . .
N22 N 0.7092(6) 0.0517(6) 0.4226(4) 0.0311(15) Uani 1 1 d . . . . .
C23 C 0.8798(8) 0.5373(7) 0.0747(5) 0.0314(18) Uani 1 1 d . . . . .
H23 H 0.8908 0.4913 0.0258 0.038 Uiso 1 1 calc R . . . .
C25 C 0.4425(7) 0.1097(8) 0.0716(5) 0.0313(18) Uani 1 1 d . . . . .
H25 H 0.4949 0.1064 0.0222 0.038 Uiso 1 1 calc R . . . .
C27 C 0.8599(8) 0.1305(9) 0.4989(5) 0.038(2) Uani 1 1 d . . . . .
C29 C 0.8872(8) 0.6645(6) 0.0726(5) 0.0294(18) Uani 1 1 d . . . . .
H29 H 0.9047 0.7109 0.0224 0.035 Uiso 1 1 calc R . . . .
C30 C 0.7736(7) 0.0417(8) 0.4943(5) 0.0299(17) Uani 1 1 d . . . . .
C31 C 0.3159(6) 0.1045(8) 0.0697(5) 0.0289(17) Uani 1 1 d . . . . .
H31 H 0.2755 0.0990 0.0194 0.035 Uiso 1 1 calc R . . . .
C37 C 0.6122(12) -0.1263(12) 0.4687(8) 0.070(4) Uani 1 1 d . . . . .
H37 H 0.5592 -0.1832 0.4585 0.084 Uiso 1 1 calc R . . . .
C38 C 0.9360(9) 0.1318(10) 0.5673(6) 0.047(2) Uani 1 1 d . . . . .
H38 H 0.9338 0.0727 0.6120 0.057 Uiso 1 1 calc R . . . .
C40 C 1.0126(11) 0.2190(12) 0.5686(7) 0.063(3) Uani 1 1 d . . . . .
H40 H 1.0650 0.2178 0.6132 0.076 Uiso 1 1 calc R . . . .
C44 C 0.7571(11) -0.0582(10) 0.5550(6) 0.055(3) Uani 1 1 d . . . . .
H44 H 0.8031 -0.0692 0.6034 0.066 Uiso 1 1 calc R . . . .
C49 C 0.9315(10) 0.3037(10) 0.4386(7) 0.051(3) Uani 1 1 d . . . . .
C53 C 0.6289(9) -0.0301(9) 0.4104(7) 0.047(2) Uani 1 1 d . . . . .
H53 H 0.5840 -0.0210 0.3614 0.056 Uiso 1 1 calc R . . . .
C54 C 0.6760(12) -0.1353(12) 0.5419(8) 0.068(3) Uani 1 1 d . . . . .
H54 H 0.6624 -0.1967 0.5836 0.081 Uiso 1 1 calc R . . . .
C57 C 1.0140(11) 0.3106(11) 0.5039(8) 0.065(3) Uani 1 1 d . . . . .
H57 H 1.0654 0.3720 0.5036 0.078 Uiso 1 1 calc R . . . .
N0AA N 0.8594(6) 0.2177(6) 0.4368(4) 0.0245(13) 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
Zn1 O1 2.167(4) . ?
Zn1 O2 2.113(5) 1_545 ?
Zn1 O3 2.039(5) . ?
Zn1 O4 2.095(5) 1_655 ?
Zn1 O8 2.050(5) . ?
Zn1 O9 2.099(5) . ?
Zn2 O1 2.116(4) . ?
Zn2 O0AA 2.037(5) . ?
Zn2 O7 2.046(5) . ?
Zn2 O11 2.110(6) . ?
Zn2 N22 2.122(6) . ?
Zn2 N0AA 2.141(6) . ?
S3 C18 1.713(6) . ?
S3 C21 1.711(7) . ?
S4 C16 1.718(7) . ?
S4 C17 1.723(7) . ?
O2 Zn1 2.113(5) 1_565 ?
O2 C14 1.270(8) . ?
O3 C20 1.241(9) . ?
O4 Zn1 2.095(5) 1_455 ?
O4 C19 1.255(9) . ?
O0AA C15 1.268(9) . ?
O7 C20 1.271(9) . ?
O8 C15 1.223(9) . ?
O10 C19 1.259(9) . ?
O12 C14 1.238(9) . ?
C14 C16 1.492(9) . ?
C15 C17 1.492(9) . ?
C16 C29 1.361(10) . ?
C17 C23 1.376(10) . ?
C18 C20 1.496(9) . ?
C18 C25 1.338(10) . ?
C19 C21 1.495(9) . ?
C21 C31 1.359(10) . ?
N22 C30 1.353(11) . ?
N22 C53 1.360(12) . ?
C23 C29 1.425(10) . ?
C25 C31 1.417(10) . ?
C27 C30 1.447(13) . ?
C27 C38 1.399(12) . ?
C27 N0AA 1.329(11) . ?
C30 C44 1.435(12) . ?
C37 C53 1.382(14) . ?
C37 C54 1.369(18) . ?
C38 C40 1.351(17) . ?
C40 C57 1.391(17) . ?
C44 C54 1.333(17) . ?
C49 C57 1.417(13) . ?
C49 N0AA 1.307(12) . ?

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 Zn1 O1 90.02(18) 1_545 . ?
O3 Zn1 O1 94.59(18) . . ?
O3 Zn1 O2 89.4(2) . 1_545 ?
O3 Zn1 O4 174.4(2) . 1_655 ?
O3 Zn1 O8 92.1(3) . . ?
O3 Zn1 O9 89.9(2) . . ?
O4 Zn1 O1 90.24(18) 1_655 . ?
O4 Zn1 O2 87.9(2) 1_655 1_545 ?
O4 Zn1 O9 85.1(2) 1_655 . ?
O8 Zn1 O1 92.78(19) . . ?
O8 Zn1 O2 176.7(2) . 1_545 ?
O8 Zn1 O4 90.4(2) . 1_655 ?
O8 Zn1 O9 90.6(2) . . ?
O9 Zn1 O1 174.21(19) . . ?
O9 Zn1 O2 86.4(2) . 1_545 ?
O1 Zn2 N22 88.3(2) . . ?
O1 Zn2 N0AA 93.4(2) . . ?
O0AA Zn2 O1 89.73(19) . . ?
O0AA Zn2 O7 98.6(2) . . ?
O0AA Zn2 O11 90.4(3) . . ?
O0AA Zn2 N22 168.9(3) . . ?
O0AA Zn2 N0AA 93.1(2) . . ?
O7 Zn2 O1 90.52(19) . . ?
O7 Zn2 O11 86.7(2) . . ?
O7 Zn2 N22 92.3(3) . . ?
O7 Zn2 N0AA 167.7(2) . . ?
O11 Zn2 O1 177.2(2) . . ?
O11 Zn2 N22 92.1(3) . . ?
O11 Zn2 N0AA 89.4(2) . . ?
N22 Zn2 N0AA 76.1(3) . . ?
C21 S3 C18 91.1(3) . . ?
C16 S4 C17 91.3(3) . . ?
Zn2 O1 Zn1 114.76(19) . . ?
C14 O2 Zn1 126.1(4) . 1_565 ?
C20 O3 Zn1 132.4(5) . . ?
C19 O4 Zn1 127.4(4) . 1_455 ?
C15 O0AA Zn2 135.1(5) . . ?
C20 O7 Zn2 137.7(4) . . ?
C15 O8 Zn1 134.4(5) . . ?
O2 C14 C16 115.8(6) . . ?
O12 C14 O2 126.6(6) . . ?
O12 C14 C16 117.6(6) . . ?
O0AA C15 C17 115.6(6) . . ?
O8 C15 O0AA 128.5(6) . . ?
O8 C15 C17 115.9(6) . . ?
C14 C16 S4 118.6(5) . . ?
C29 C16 S4 112.5(5) . . ?
C29 C16 C14 128.9(6) . . ?
C15 C17 S4 120.9(5) . . ?
C23 C17 S4 111.7(5) . . ?
C23 C17 C15 127.4(6) . . ?
C20 C18 S3 119.5(5) . . ?
C25 C18 S3 111.9(5) . . ?
C25 C18 C20 128.6(6) . . ?
O4 C19 O10 127.0(6) . . ?
O4 C19 C21 116.2(6) . . ?
O10 C19 C21 116.8(6) . . ?
O3 C20 O7 128.3(6) . . ?
O3 C20 C18 116.5(6) . . ?
O7 C20 C18 115.2(6) . . ?
C19 C21 S3 119.5(5) . . ?
C31 C21 S3 112.3(5) . . ?
C31 C21 C19 128.2(6) . . ?
C30 N22 Zn2 116.0(6) . . ?
C30 N22 C53 120.1(7) . . ?
C53 N22 Zn2 124.0(6) . . ?
C17 C23 C29 112.3(6) . . ?
C18 C25 C31 113.5(6) . . ?
C38 C27 C30 123.1(9) . . ?
N0AA C27 C30 116.7(7) . . ?
N0AA C27 C38 120.1(9) . . ?
C16 C29 C23 112.2(6) . . ?
N22 C30 C27 115.4(7) . . ?
N22 C30 C44 118.3(9) . . ?
C44 C30 C27 126.1(8) . . ?
C21 C31 C25 111.3(7) . . ?
C54 C37 C53 118.0(11) . . ?
C40 C38 C27 120.0(9) . . ?
C38 C40 C57 120.8(9) . . ?
C54 C44 C30 120.0(10) . . ?
N0AA C49 C57 123.7(10) . . ?
N22 C53 C37 121.9(10) . . ?
C44 C54 C37 121.6(10) . . ?
C40 C57 C49 115.2(10) . . ?
C27 N0AA Zn2 115.4(6) . . ?
C49 N0AA Zn2 124.3(6) . . ?
C49 N0AA C27 120.1(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
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 0.500 0.500 0.305 781 119 ' '
_platon_squeeze_details          ?
