# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_compound_3
_database_code_depnum_ccdc_archive 'CCDC 1448143'
_audit_update_record             
;
2016-01-18 deposited with the CCDC.
2016-02-23 downloaded from the CCDC.
;
_audit_creation_date             2016-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H16 F6 N4 O6 S2 Zn'
_chemical_formula_sum            'C22 H16 F6 N4 O6 S2 Zn'
_chemical_formula_weight         675.88
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H16 F6 N4 O6 S2 Zn1'
_chemical_oxdiff_usercomment     "James's C101-B1"
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'
F F 0.0171 0.0103 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   9.92044(14)
_cell_length_b                   14.02733(18)
_cell_length_c                   18.6185(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.5148(13)
_cell_angle_gamma                90
_cell_volume                     2538.75(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8909
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      32.0180
_cell_measurement_theta_min      3.6490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.224
_exptl_absorpt_correction_T_max  0.871
_exptl_absorpt_correction_T_min  0.780
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.2637
_exptl_crystal_size_mid          0.2049
_exptl_crystal_size_min          0.1378
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16102
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         32.163
_diffrn_reflns_theta_min         3.652
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -46.00   47.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       24.8712  -37.0000  -90.0000 93

#__ type_ start__ end____ width___ exp.time_
  2 omega  -47.00   63.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       24.8712  -19.0000    0.0000 110

#__ type_ start__ end____ width___ exp.time_
  3 omega   -4.00   94.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       24.8712   77.0000 -120.0000 98

#__ type_ start__ end____ width___ exp.time_
  4 omega   35.00   99.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       24.8712  178.0000  -90.0000 64

#__ type_ start__ end____ width___ exp.time_
  5 omega    6.00   59.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       24.8712   57.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
  6 omega    6.00   93.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       24.8712   57.0000   60.0000 87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0647743000
_diffrn_orient_matrix_UB_12      -0.0206085000
_diffrn_orient_matrix_UB_13      0.0013114000
_diffrn_orient_matrix_UB_21      0.0293274000
_diffrn_orient_matrix_UB_22      -0.0230901000
_diffrn_orient_matrix_UB_23      0.0333469000
_diffrn_orient_matrix_UB_31      -0.0164052000
_diffrn_orient_matrix_UB_32      0.0399864000
_diffrn_orient_matrix_UB_33      0.0199405000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3763
_reflns_number_total             4183
_reflns_odcompleteness_completeness 99.71
_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, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         4183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0274
_refine_ls_restrained_S_all      1.054
_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)+(0.0276P)²+3.0392P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0665
_refine_ls_wR_factor_ref         0.0691
_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:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.74197(15) 0.19262(10) 0.28906(8) 0.0206(3) Uani 1 1 d . . . . .
H1 H 0.7543 0.2038 0.2405 0.025 Uiso 1 1 calc R . . . .
C2 C 0.83270(15) 0.13249(10) 0.33380(9) 0.0246(3) Uani 1 1 d . . . . .
H2 H 0.9063 0.1030 0.3165 0.029 Uiso 1 1 calc R . . . .
C3 C 0.81364(15) 0.11638(10) 0.40413(9) 0.0240(3) Uani 1 1 d . . . . .
H3 H 0.8747 0.0758 0.4362 0.029 Uiso 1 1 calc R . . . .
C4 C 0.70489(15) 0.15968(9) 0.42777(8) 0.0205(3) Uani 1 1 d . . . . .
H4 H 0.6898 0.1488 0.4759 0.025 Uiso 1 1 calc R . . . .
C5 C 0.61826(13) 0.21932(9) 0.37994(7) 0.0155(2) Uani 1 1 d . . . . .
C6 C 0.50083(13) 0.27052(9) 0.40040(7) 0.0151(2) Uani 1 1 d . . . . .
C7 C 0.47140(15) 0.26593(10) 0.47008(7) 0.0201(3) Uani 1 1 d . . . . .
H7 H 0.5232 0.2253 0.5062 0.024 Uiso 1 1 calc R . . . .
C8 C 0.36606(16) 0.32097(11) 0.48647(8) 0.0234(3) Uani 1 1 d . . . . .
H8 H 0.3469 0.3205 0.5345 0.028 Uiso 1 1 calc R . . . .
C9 C 0.28916(15) 0.37647(11) 0.43231(8) 0.0228(3) Uani 1 1 d . . . . .
H9 H 0.2153 0.4142 0.4421 0.027 Uiso 1 1 calc R . . . .
C10 C 0.32147(14) 0.37622(10) 0.36341(8) 0.0191(2) Uani 1 1 d . . . . .
H10 H 0.2674 0.4135 0.3258 0.023 Uiso 1 1 calc R . . . .
C11 C 0.11600(16) 0.47455(12) 0.13567(9) 0.0273(3) Uani 1 1 d . . . . .
F1 F 0.08894(12) 0.38175(9) 0.13313(8) 0.0528(3) Uani 1 1 d . . . . .
F2 F 0.04357(11) 0.51265(9) 0.07498(6) 0.0458(3) Uani 1 1 d . . . . .
F3 F 0.07058(11) 0.51191(10) 0.19135(6) 0.0442(3) Uani 1 1 d . . . . .
N1 N 0.63782(11) 0.23544(8) 0.31168(6) 0.0157(2) Uani 1 1 d . . . . .
N2 N 0.42621(11) 0.32529(8) 0.34784(6) 0.0148(2) Uani 1 1 d . . . . .
O1 O 0.35807(10) 0.44924(7) 0.21115(5) 0.01921(19) Uani 1 1 d . . . . .
O2 O 0.32846(12) 0.45167(8) 0.07814(6) 0.0269(2) Uani 1 1 d . . . . .
O3 O 0.30994(12) 0.59783(7) 0.14562(6) 0.0250(2) Uani 1 1 d . . . . .
S1 S 0.29877(3) 0.49619(2) 0.14259(2) 0.01517(7) Uani 1 1 d . . . . .
Zn1 Zn 0.5000 0.33290(2) 0.2500 0.01282(6) Uani 1 2 d S T 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 H1 0.9500 . ?
C1 C2 1.384(2) . ?
C1 N1 1.3340(17) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3878(18) . ?
C5 C6 1.4816(18) . ?
C5 N1 1.3425(16) . ?
C6 C7 1.3871(17) . ?
C6 N2 1.3440(16) . ?
C7 H7 0.9500 . ?
C7 C8 1.381(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.378(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.3830(19) . ?
C10 H10 0.9500 . ?
C10 N2 1.3395(17) . ?
C11 F1 1.328(2) . ?
C11 F2 1.3246(18) . ?
C11 F3 1.3186(19) . ?
C11 S1 1.8174(16) . ?
N1 Zn1 2.1048(11) . ?
N2 Zn1 2.0972(11) . ?
O1 S1 1.4523(10) . ?
O1 Zn1 2.1823(9) . ?
O2 S1 1.4345(10) . ?
O3 S1 1.4304(11) . ?
Zn1 N1 2.1047(11) 2_655 ?
Zn1 N2 2.0972(11) 2_655 ?
Zn1 O1 2.1823(10) 2_655 ?

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
C2 C1 H1 118.8 . . ?
N1 C1 H1 118.8 . . ?
N1 C1 C2 122.40(13) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.40(13) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.57(13) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.85(13) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 123.04(12) . . ?
N1 C5 C4 121.40(13) . . ?
N1 C5 C6 115.55(11) . . ?
C7 C6 C5 122.75(12) . . ?
N2 C6 C5 115.92(11) . . ?
N2 C6 C7 121.29(12) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.36(13) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.14(13) . . ?
C9 C8 H8 120.4 . . ?
C8 C9 H9 120.6 . . ?
C8 C9 C10 118.72(13) . . ?
C10 C9 H9 120.6 . . ?
C9 C10 H10 118.8 . . ?
N2 C10 C9 122.37(13) . . ?
N2 C10 H10 118.8 . . ?
F1 C11 S1 110.97(11) . . ?
F2 C11 F1 107.08(14) . . ?
F2 C11 S1 110.90(12) . . ?
F3 C11 F1 108.62(15) . . ?
F3 C11 F2 107.34(13) . . ?
F3 C11 S1 111.75(11) . . ?
C1 N1 C5 119.37(12) . . ?
C1 N1 Zn1 125.44(9) . . ?
C5 N1 Zn1 115.15(9) . . ?
C6 N2 Zn1 115.11(9) . . ?
C10 N2 C6 119.06(11) . . ?
C10 N2 Zn1 125.53(9) . . ?
S1 O1 Zn1 138.75(6) . . ?
O1 S1 C11 102.12(7) . . ?
O2 S1 C11 103.68(7) . . ?
O2 S1 O1 115.02(6) . . ?
O3 S1 C11 103.75(7) . . ?
O3 S1 O1 113.75(6) . . ?
O3 S1 O2 116.09(7) . . ?
N1 Zn1 N1 98.99(6) 2_655 . ?
N1 Zn1 O1 166.51(4) 2_655 2_655 ?
N1 Zn1 O1 166.51(4) . . ?
N1 Zn1 O1 89.94(4) 2_655 . ?
N1 Zn1 O1 89.94(4) . 2_655 ?
N2 Zn1 N1 78.13(4) 2_655 2_655 ?
N2 Zn1 N1 98.02(4) . 2_655 ?
N2 Zn1 N1 98.02(4) 2_655 . ?
N2 Zn1 N1 78.13(4) . . ?
N2 Zn1 N2 174.16(6) 2_655 . ?
N2 Zn1 O1 90.69(4) . . ?
N2 Zn1 O1 90.69(4) 2_655 2_655 ?
N2 Zn1 O1 93.68(4) 2_655 . ?
N2 Zn1 O1 93.68(4) . 2_655 ?
O1 Zn1 O1 83.20(5) . 2_655 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.5(2) . . . . ?
C2 C1 N1 C5 -0.8(2) . . . . ?
C2 C1 N1 Zn1 176.95(11) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C3 C4 C5 C6 -178.72(12) . . . . ?
C3 C4 C5 N1 0.1(2) . . . . ?
C4 C5 C6 C7 2.7(2) . . . . ?
C4 C5 C6 N2 -179.72(12) . . . . ?
C4 C5 N1 C1 0.59(19) . . . . ?
C4 C5 N1 Zn1 -177.38(10) . . . . ?
C5 C6 C7 C8 175.45(12) . . . . ?
C5 C6 N2 C10 -177.67(11) . . . . ?
C5 C6 N2 Zn1 -3.61(14) . . . . ?
C6 C5 N1 C1 179.53(12) . . . . ?
C6 C5 N1 Zn1 1.56(14) . . . . ?
C6 C7 C8 C9 2.5(2) . . . . ?
C7 C6 N2 C10 -0.03(18) . . . . ?
C7 C6 N2 Zn1 174.03(10) . . . . ?
C7 C8 C9 C10 -0.9(2) . . . . ?
C8 C9 C10 N2 -1.2(2) . . . . ?
C9 C10 N2 C6 1.7(2) . . . . ?
C9 C10 N2 Zn1 -171.73(10) . . . . ?
F1 C11 S1 O1 -60.84(13) . . . . ?
F1 C11 S1 O2 58.99(13) . . . . ?
F1 C11 S1 O3 -179.31(12) . . . . ?
F2 C11 S1 O1 -179.73(11) . . . . ?
F2 C11 S1 O2 -59.89(13) . . . . ?
F2 C11 S1 O3 61.81(13) . . . . ?
F3 C11 S1 O1 60.55(13) . . . . ?
F3 C11 S1 O2 -179.61(12) . . . . ?
F3 C11 S1 O3 -57.91(13) . . . . ?
N1 C1 C2 C3 0.3(2) . . . . ?
N1 C5 C6 C7 -176.23(12) . . . . ?
N1 C5 C6 N2 1.37(16) . . . . ?
N2 C6 C7 C8 -2.03(19) . . . . ?
Zn1 O1 S1 C11 118.67(10) . . . . ?
Zn1 O1 S1 O2 7.12(13) . . . . ?
Zn1 O1 S1 O3 -130.23(9) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 1 0.0418 0.0003 0.0006 1.0001 0.0013 0.0333 0.0200
2 -5 -1 0.1379 2.0006 -4.9989 -0.9996 -0.0279 0.1408 -0.2526
-2 5 1 0.1379 -2.0006 4.9989 0.9996 0.0279 -0.1408 0.2526
0 -1 -5 0.1043 -0.0017 -1.0027 -5.0006 0.0142 -0.1437 -0.1398
-1 2 -5 0.1033 -1.0022 1.9963 -5.0009 0.0172 -0.2423 -0.0035
-5 -5 2 0.1106 -5.0009 -4.9971 2.0002 0.4295 0.0354 -0.0779
5 5 -2 0.0943 5.0009 4.9971 -2.0002 -0.4295 -0.0354 0.0779
-3 3 5 0.0960 -2.9995 3.0020 5.0002 0.1390 0.0095 0.2690
3 -3 -5 0.0960 2.9995 -3.0020 -5.0002 -0.1390 -0.0095 -0.2690
1 1 -5 0.0913 0.9986 0.9966 -5.0007 -0.0918 -0.1605 -0.0762
0 5 -1 0.1426 -0.0006 4.9977 -1.0005 -0.1043 -0.1488 0.1799
1 -1 -5 0.0945 0.9987 -1.0027 -5.0005 -0.0506 -0.1143 -0.1562
-1 -3 5 0.1051 -0.9985 -2.9959 5.0008 0.1330 0.2067 -0.0037
1 -1 5 0.0503 1.0022 -0.9966 5.0008 -0.0378 0.2192 0.0434
-2 5 -4 0.1253 -2.0024 4.9959 -4.0011 0.0215 -0.3075 0.1528
0 0 -1 0.0960 -0.0003 -0.0006 -1.0001 -0.0013 -0.0333 -0.0200
-5 5 -1 0.1082 -5.0024 4.9977 -1.0009 0.2197 -0.2955 0.2619
-3 0 -5 0.1157 -3.0028 -0.0030 -5.0009 0.1880 -0.2548 -0.0506
-1 -2 -5 0.1123 -1.0020 -2.0023 -5.0006 0.0996 -0.1499 -0.1633
5 -5 2 0.0810 5.0028 -4.9971 2.0011 -0.2184 0.3288 -0.2420

_olex2_date_sample_data_collection 1409219341.36
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_description       plate
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_compound_4
_database_code_depnum_ccdc_archive 'CCDC 1448144'
_audit_update_record             
;
2016-01-18 deposited with the CCDC.
2016-02-23 downloaded from the CCDC.
;
_audit_creation_date             2016-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C26 H16 F6 N4 O6 S2 Zn'
_chemical_formula_sum            'C26 H16 F6 N4 O6 S2 Zn'
_chemical_formula_weight         723.92
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H16 F6 N4 O6 S2 Zn1'
_chemical_oxdiff_usercomment     'James C101-B3'
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'
F F 0.0171 0.0103 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   9.75476(12)
_cell_length_b                   14.26536(17)
_cell_length_c                   19.5942(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.2384(11)
_cell_angle_gamma                90
_cell_volume                     2715.24(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6506
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      31.9100
_cell_measurement_theta_min      3.8750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.151
_exptl_absorpt_correction_T_max  0.898
_exptl_absorpt_correction_T_min  0.846
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.2088
_exptl_crystal_size_mid          0.1305
_exptl_crystal_size_min          0.1221
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12898
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         32.080
_diffrn_reflns_theta_min         3.402
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -4.00   94.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       24.7780   77.0000 -150.0000 98

#__ type_ start__ end____ width___ exp.time_
  2 omega   -2.00   93.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       24.7780   73.0000  102.0000 95

#__ type_ start__ end____ width___ exp.time_
  3 omega   35.00   99.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       24.7780  178.0000 -120.0000 64

#__ type_ start__ end____ width___ exp.time_
  4 omega  -44.00   53.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       24.7780  -77.0000   90.0000 97

#__ type_ start__ end____ width___ exp.time_
  5 omega   34.00   59.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       24.7780 -178.0000    0.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0296920000
_diffrn_orient_matrix_UB_12      -0.0301645000
_diffrn_orient_matrix_UB_13      0.0233733000
_diffrn_orient_matrix_UB_21      -0.0219415000
_diffrn_orient_matrix_UB_22      0.0395247000
_diffrn_orient_matrix_UB_23      0.0180890000
_diffrn_orient_matrix_UB_31      -0.0629991000
_diffrn_orient_matrix_UB_32      0.0004374000
_diffrn_orient_matrix_UB_33      -0.0211614000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3895
_reflns_number_total             4395
_reflns_odcompleteness_completeness 99.69
_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, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         4395
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0271
_refine_ls_restrained_S_all      1.051
_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)+(0.0329P)²+2.2802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0689
_refine_ls_wR_factor_ref         0.0722
_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:
 C1(H1), C2(H2), C3(H3), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.23762(15) 0.21337(9) 0.28432(7) 0.0213(3) Uani 1 1 d . . . . .
H1 H 0.2613 0.2227 0.2388 0.026 Uiso 1 1 calc R . . . .
C2 C 0.31872(16) 0.15249(10) 0.32755(8) 0.0260(3) Uani 1 1 d . . . . .
H2 H 0.3958 0.1214 0.3116 0.031 Uiso 1 1 calc R . . . .
C3 C 0.28458(16) 0.13883(9) 0.39313(8) 0.0251(3) Uani 1 1 d . . . . .
H3 H 0.3391 0.0987 0.4233 0.030 Uiso 1 1 calc R . . . .
C4 C 0.16887(15) 0.18416(9) 0.41574(7) 0.0199(3) Uani 1 1 d . . . . .
C5 C 0.09413(13) 0.24374(9) 0.36900(6) 0.0156(2) Uani 1 1 d . . . . .
C6 C -0.02262(13) 0.29459(9) 0.38981(6) 0.0153(2) Uani 1 1 d . . . . .
C7 C -0.05773(14) 0.28673(9) 0.45741(6) 0.0182(2) Uani 1 1 d . . . . .
C8 C 0.02001(16) 0.22438(10) 0.50380(7) 0.0236(3) Uani 1 1 d . . . . .
H8 H -0.0047 0.2178 0.5493 0.028 Uiso 1 1 calc R . . . .
C9 C 0.12752(16) 0.17502(10) 0.48385(7) 0.0244(3) Uani 1 1 d . . . . .
H9 H 0.1765 0.1337 0.5153 0.029 Uiso 1 1 calc R . . . .
C10 C -0.16677(16) 0.34267(10) 0.47658(7) 0.0223(3) Uani 1 1 d . . . . .
H10 H -0.1913 0.3416 0.5224 0.027 Uiso 1 1 calc R . . . .
C11 C -0.23730(16) 0.39883(10) 0.42851(7) 0.0226(3) Uani 1 1 d . . . . .
H11 H -0.3123 0.4360 0.4405 0.027 Uiso 1 1 calc R . . . .
C12 C -0.19742(14) 0.40076(9) 0.36172(7) 0.0189(2) Uani 1 1 d . . . . .
H12 H -0.2477 0.4391 0.3286 0.023 Uiso 1 1 calc R . . . .
C13 C -0.37271(15) 0.49574(11) 0.14606(8) 0.0241(3) Uani 1 1 d . . . . .
F1 F -0.40213(11) 0.40510(8) 0.15350(6) 0.0411(3) Uani 1 1 d . . . . .
F2 F -0.43500(10) 0.52293(8) 0.08597(5) 0.0367(2) Uani 1 1 d . . . . .
F3 F -0.42742(11) 0.54391(9) 0.19469(6) 0.0432(3) Uani 1 1 d . . . . .
N1 N 0.12929(12) 0.25829(8) 0.30452(5) 0.0163(2) Uani 1 1 d . . . . .
N2 N -0.09211(11) 0.35113(7) 0.34284(5) 0.0149(2) Uani 1 1 d . . . . .
O1 O -0.13741(10) 0.47239(7) 0.21387(5) 0.02013(19) Uani 1 1 d . . . . .
O2 O -0.15031(11) 0.46501(7) 0.08885(5) 0.0224(2) Uani 1 1 d . . . . .
O3 O -0.17417(12) 0.61458(7) 0.14702(5) 0.0240(2) Uani 1 1 d . . . . .
S1 S -0.18743(3) 0.51437(2) 0.14835(2) 0.01482(7) Uani 1 1 d . . . . .
Zn1 Zn 0.0000 0.35805(2) 0.2500 0.01376(6) Uani 1 2 d S T 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 H1 0.9500 . ?
C1 C2 1.405(2) . ?
C1 N1 1.3269(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.370(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.407(2) . ?
C4 C5 1.4038(17) . ?
C4 C9 1.435(2) . ?
C5 C6 1.4403(18) . ?
C5 N1 1.3549(16) . ?
C6 C7 1.4025(17) . ?
C6 N2 1.3575(16) . ?
C7 C8 1.4376(19) . ?
C7 C10 1.408(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.350(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.373(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.3992(19) . ?
C12 H12 0.9500 . ?
C12 N2 1.3277(17) . ?
C13 F1 1.3354(18) . ?
C13 F2 1.3325(17) . ?
C13 F3 1.3258(18) . ?
C13 S1 1.8233(15) . ?
N1 Zn1 2.1239(11) . ?
N2 Zn1 2.1036(11) . ?
O1 S1 1.4595(9) . ?
O1 Zn1 2.1875(9) . ?
O2 S1 1.4365(10) . ?
O3 S1 1.4359(10) . ?
Zn1 N1 2.1239(11) 2 ?
Zn1 N2 2.1036(11) 2 ?
Zn1 O1 2.1875(9) 2 ?

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
C2 C1 H1 118.7 . . ?
N1 C1 H1 118.7 . . ?
N1 C1 C2 122.57(14) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.78(14) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.03(13) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C9 123.55(13) . . ?
C5 C4 C3 117.17(13) . . ?
C5 C4 C9 119.24(13) . . ?
C4 C5 C6 119.81(12) . . ?
N1 C5 C4 122.71(12) . . ?
N1 C5 C6 117.44(11) . . ?
C7 C6 C5 119.65(11) . . ?
N2 C6 C5 117.78(11) . . ?
N2 C6 C7 122.54(12) . . ?
C6 C7 C8 119.11(13) . . ?
C6 C7 C10 117.53(12) . . ?
C10 C7 C8 123.35(12) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.22(13) . . ?
C9 C8 H8 119.4 . . ?
C4 C9 H9 119.5 . . ?
C8 C9 C4 120.90(13) . . ?
C8 C9 H9 119.5 . . ?
C7 C10 H10 120.3 . . ?
C11 C10 C7 119.43(12) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.24(13) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 118.7 . . ?
N2 C12 C11 122.57(13) . . ?
N2 C12 H12 118.7 . . ?
F1 C13 S1 111.15(10) . . ?
F2 C13 F1 107.04(12) . . ?
F2 C13 S1 110.51(11) . . ?
F3 C13 F1 108.59(13) . . ?
F3 C13 F2 107.66(13) . . ?
F3 C13 S1 111.71(11) . . ?
C1 N1 C5 118.72(12) . . ?
C1 N1 Zn1 128.76(9) . . ?
C5 N1 Zn1 112.48(8) . . ?
C6 N2 Zn1 112.82(8) . . ?
C12 N2 C6 118.63(11) . . ?
C12 N2 Zn1 128.20(9) . . ?
S1 O1 Zn1 137.42(6) . . ?
O1 S1 C13 102.29(6) . . ?
O2 S1 C13 103.38(7) . . ?
O2 S1 O1 115.09(6) . . ?
O3 S1 C13 103.61(7) . . ?
O3 S1 O1 113.65(6) . . ?
O3 S1 O2 116.32(6) . . ?
N1 Zn1 N1 95.86(6) 2 . ?
N1 Zn1 O1 91.07(4) . 2 ?
N1 Zn1 O1 168.69(4) 2 2 ?
N1 Zn1 O1 91.07(4) 2 . ?
N1 Zn1 O1 168.69(4) . . ?
N2 Zn1 N1 79.31(4) 2 2 ?
N2 Zn1 N1 79.31(4) . . ?
N2 Zn1 N1 97.05(4) . 2 ?
N2 Zn1 N1 97.05(4) 2 . ?
N2 Zn1 N2 174.62(6) 2 . ?
N2 Zn1 O1 91.00(4) 2 2 ?
N2 Zn1 O1 93.01(4) . 2 ?
N2 Zn1 O1 91.00(4) . . ?
N2 Zn1 O1 93.01(4) 2 . ?
O1 Zn1 O1 83.57(5) . 2 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 1.0(2) . . . . ?
C2 C1 N1 C5 -1.1(2) . . . . ?
C2 C1 N1 Zn1 176.43(10) . . . . ?
C2 C3 C4 C5 -1.1(2) . . . . ?
C2 C3 C4 C9 -178.83(13) . . . . ?
C3 C4 C5 C6 -177.92(12) . . . . ?
C3 C4 C5 N1 0.08(19) . . . . ?
C3 C4 C9 C8 176.23(13) . . . . ?
C4 C5 C6 C7 2.27(18) . . . . ?
C4 C5 C6 N2 -179.77(11) . . . . ?
C4 C5 N1 C1 1.00(18) . . . . ?
C4 C5 N1 Zn1 -176.91(9) . . . . ?
C5 C4 C9 C8 -1.5(2) . . . . ?
C5 C6 C7 C8 -2.90(18) . . . . ?
C5 C6 C7 C10 175.75(11) . . . . ?
C5 C6 N2 C12 -177.96(11) . . . . ?
C5 C6 N2 Zn1 -4.25(14) . . . . ?
C6 C5 N1 C1 179.05(11) . . . . ?
C6 C5 N1 Zn1 1.14(14) . . . . ?
C6 C7 C8 C9 1.39(19) . . . . ?
C6 C7 C10 C11 2.75(19) . . . . ?
C7 C6 N2 C12 -0.07(18) . . . . ?
C7 C6 N2 Zn1 173.65(9) . . . . ?
C7 C8 C9 C4 0.8(2) . . . . ?
C7 C10 C11 C12 -1.3(2) . . . . ?
C8 C7 C10 C11 -178.67(13) . . . . ?
C9 C4 C5 C6 -0.09(18) . . . . ?
C9 C4 C5 N1 177.91(12) . . . . ?
C10 C7 C8 C9 -177.17(13) . . . . ?
C10 C11 C12 N2 -1.0(2) . . . . ?
C11 C12 N2 C6 1.65(19) . . . . ?
C11 C12 N2 Zn1 -170.98(10) . . . . ?
F1 C13 S1 O1 -55.81(12) . . . . ?
F1 C13 S1 O2 64.06(12) . . . . ?
F1 C13 S1 O3 -174.17(10) . . . . ?
F2 C13 S1 O1 -174.50(10) . . . . ?
F2 C13 S1 O2 -54.64(12) . . . . ?
F2 C13 S1 O3 67.13(12) . . . . ?
F3 C13 S1 O1 65.66(12) . . . . ?
F3 C13 S1 O2 -174.47(11) . . . . ?
F3 C13 S1 O3 -52.70(12) . . . . ?
N1 C1 C2 C3 0.1(2) . . . . ?
N1 C5 C6 C7 -175.84(11) . . . . ?
N1 C5 C6 N2 2.12(17) . . . . ?
N2 C6 C7 C8 179.24(11) . . . . ?
N2 C6 C7 C10 -2.11(18) . . . . ?
Zn1 O1 S1 C13 118.88(10) . . . . ?
Zn1 O1 S1 O2 7.57(12) . . . . ?
Zn1 O1 S1 O3 -130.12(9) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 -1 28 0.0509 0.0000 -1.0000 28.0000 0.6846 0.4670 -0.5930
-14 0 2 0.0755 -14.0000 0.0000 2.0000 0.4624 0.3434 0.8397
-2 1 -27 0.0638 -2.0000 1.0000 -27.0000 -0.6019 -0.4050 0.6978
10 -10 12 0.0697 10.0000 -10.0000 12.0000 0.2852 -0.3976 -0.8883
9 11 12 0.0746 9.0000 11.0000 12.0000 -0.3186 0.4544 -0.8161
-6 -16 -9 0.1065 -6.0000 -16.0000 -9.0000 0.4504 -0.6635 0.5614
12 10 -2 0.0626 12.0000 10.0000 -2.0000 -0.7047 0.0958 -0.7093
-9 -14 12 0.0871 -9.0000 -14.0000 12.0000 0.9700 -0.1388 0.3069
-6 -7 24 0.0647 -6.0000 -7.0000 24.0000 0.9503 0.2891 -0.1329
-13 -6 9 0.0783 -13.0000 -6.0000 9.0000 0.7773 0.2109 0.6259
9 7 -20 0.0746 9.0000 7.0000 -20.0000 -0.9458 -0.2826 -0.1407
8 -7 -22 0.0837 8.0000 -7.0000 -22.0000 -0.5406 -0.8502 -0.0415
-11 7 14 0.0653 -11.0000 7.0000 14.0000 0.4427 0.7713 0.3998
-11 11 4 0.0604 -11.0000 11.0000 4.0000 0.0883 0.7485 0.6132
12 -10 -1 0.0674 12.0000 -10.0000 -1.0000 -0.0780 -0.6766 -0.7392
-10 13 -5 0.0500 -10.0000 13.0000 -5.0000 -0.2121 0.6428 0.7415

_olex2_date_sample_data_collection 1409666177.15
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_description       block
####################################################################### 
# 
# 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_compound_5
_database_code_depnum_ccdc_archive 'CCDC 1448145'
_audit_update_record             
;
2016-01-18 deposited with the CCDC.
2016-02-23 downloaded from the CCDC.
;
_audit_creation_date             2014-09-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H32 F3 N8 O3 S Zn, C F3 O3 S'
_chemical_formula_sum            'C24 H32 F6 N8 O6 S2 Zn'
_chemical_formula_weight         772.06
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 H32 F6 N8 O6 S2 Zn1'
_chemical_oxdiff_usercomment     'James C101-B2'
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'
F F 0.0171 0.0103 '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           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   8.3731(3)
_cell_length_b                   8.6907(3)
_cell_length_c                   11.7281(5)
_cell_angle_alpha                68.851(3)
_cell_angle_beta                 81.968(3)
_cell_angle_gamma                82.401(3)
_cell_volume                     785.04(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    7999
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      31.9730
_cell_measurement_theta_min      3.7120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.004
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.848
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.2125
_exptl_crystal_size_mid          0.1858
_exptl_crystal_size_min          0.0806
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14482
_diffrn_reflns_point_group_measured_fraction_full 0.888
_diffrn_reflns_point_group_measured_fraction_max 0.766
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         32.092
_diffrn_reflns_theta_min         3.258
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    6.00   93.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       24.8712   57.0000  -60.0000 87

#__ type_ start__ end____ width___ exp.time_
  2 omega    6.00   93.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       24.8712   57.0000 -120.0000 87

#__ type_ start__ end____ width___ exp.time_
  3 omega   -4.00   94.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       24.8712   77.0000   30.0000 98

#__ type_ start__ end____ width___ exp.time_
  4 omega  -20.00   65.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       24.8712  -99.0000  150.0000 85

#__ type_ start__ end____ width___ exp.time_
  5 omega  -44.00   54.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       24.8712  -77.0000  -90.0000 98

#__ type_ start__ end____ width___ exp.time_
  6 omega   -4.00   94.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       24.8712   77.0000  -60.0000 98

#__ type_ start__ end____ width___ exp.time_
  7 omega -100.00  -55.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -25.4962  178.0000  -30.0000 45

#__ type_ start__ end____ width___ exp.time_
  8 omega  -63.00   47.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -25.4962   19.0000 -120.0000 110

#__ type_ start__ end____ width___ exp.time_
  9 omega    2.00   35.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       24.8712   37.0000 -180.0000 33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0381285000
_diffrn_orient_matrix_UB_12      -0.0273436000
_diffrn_orient_matrix_UB_13      -0.0387238000
_diffrn_orient_matrix_UB_21      -0.0764525000
_diffrn_orient_matrix_UB_22      0.0128411000
_diffrn_orient_matrix_UB_23      0.0314495000
_diffrn_orient_matrix_UB_31      -0.0088418000
_diffrn_orient_matrix_UB_32      0.0824988000
_diffrn_orient_matrix_UB_33      -0.0419349000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.660
_reflns_Friedel_fraction_full    0.778
_reflns_Friedel_fraction_max     0.609
_reflns_number_gt                7971
_reflns_number_total             8455
_reflns_odcompleteness_completeness 99.81
_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, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 
;
 Flack x determined using 2928 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.037(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     432
_refine_ls_number_reflns         8455
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0304
_refine_ls_restrained_S_all      0.966
_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)+(0.0094P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0525
_refine_ls_wR_factor_ref         0.0539
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C14(H14), C20(H20)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C11(H11A,H11B,H11C),
 C12(H12A,H12B,H12C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C22(H22A,H22B,
 H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.3740(4) 0.8479(4) 0.2347(2) 0.0266(7) Uani 1 1 d . . . . .
H1A H 0.4902 0.8160 0.2236 0.040 Uiso 1 1 calc GR . . . .
H1B H 0.3500 0.9628 0.1815 0.040 Uiso 1 1 calc GR . . . .
H1C H 0.3132 0.7750 0.2131 0.040 Uiso 1 1 calc GR . . . .
C2 C 0.3260(3) 0.8322(3) 0.3656(2) 0.0171(5) Uani 1 1 d . . . . .
C3 C 0.2201(4) 0.9373(3) 0.4131(3) 0.0206(6) Uani 1 1 d . . . . .
H3 H 0.1596 1.0353 0.3672 0.025 Uiso 1 1 calc R . . . .
C4 C 0.2198(3) 0.8729(3) 0.5383(3) 0.0180(6) Uani 1 1 d . . . . .
C5 C 0.1338(4) 0.9330(4) 0.6364(3) 0.0257(7) Uani 1 1 d . . . . .
H5A H 0.0806 0.8421 0.7007 0.038 Uiso 1 1 calc GR . . . .
H5B H 0.0523 1.0238 0.6011 0.038 Uiso 1 1 calc GR . . . .
H5C H 0.2119 0.9727 0.6720 0.038 Uiso 1 1 calc GR . . . .
C6 C 0.3645(3) 0.6129(3) 0.6803(2) 0.0141(6) Uani 1 1 d . . . . .
H6A H 0.2938 0.6370 0.7480 0.017 Uiso 1 1 calc R . . . .
H6B H 0.3470 0.5004 0.6845 0.017 Uiso 1 1 calc R . . . .
C7 C 0.4909(4) 0.6915(4) 0.8848(2) 0.0188(6) Uani 1 1 d . . . . .
H7A H 0.4193 0.7912 0.8482 0.028 Uiso 1 1 calc GR . . . .
H7B H 0.5599 0.7130 0.9373 0.028 Uiso 1 1 calc GR . . . .
H7C H 0.4256 0.6000 0.9341 0.028 Uiso 1 1 calc GR . . . .
C8 C 0.5942(3) 0.6463(3) 0.7854(2) 0.0139(5) Uani 1 1 d . . . . .
C9 C 0.7598(3) 0.6224(3) 0.7638(2) 0.0151(5) Uani 1 1 d . . . . .
H9 H 0.8382 0.6343 0.8106 0.018 Uiso 1 1 calc R . . . .
C10 C 0.7900(3) 0.5773(3) 0.6596(2) 0.0139(5) Uani 1 1 d . . . . .
C11 C 0.9491(3) 0.5328(4) 0.5989(3) 0.0203(6) Uani 1 1 d . . . . .
H11A H 0.9369 0.4471 0.5655 0.030 Uiso 1 1 calc GR . . . .
H11B H 1.0288 0.4910 0.6592 0.030 Uiso 1 1 calc GR . . . .
H11C H 0.9860 0.6313 0.5320 0.030 Uiso 1 1 calc GR . . . .
C12 C 0.2475(3) 0.3924(4) 0.3941(3) 0.0209(6) Uani 1 1 d . . . . .
H12A H 0.2673 0.3582 0.4805 0.031 Uiso 1 1 calc GR . . . .
H12B H 0.1760 0.3180 0.3848 0.031 Uiso 1 1 calc GR . . . .
H12C H 0.1962 0.5060 0.3671 0.031 Uiso 1 1 calc GR . . . .
C13 C 0.4050(3) 0.3848(3) 0.3174(2) 0.0155(5) Uani 1 1 d . . . . .
C14 C 0.4372(3) 0.3337(3) 0.2157(2) 0.0157(5) Uani 1 1 d . . . . .
H14 H 0.3623 0.2951 0.1807 0.019 Uiso 1 1 calc R . . . .
C15 C 0.5981(3) 0.3505(3) 0.1765(2) 0.0141(5) Uani 1 1 d . . . . .
C16 C 0.7003(3) 0.3097(4) 0.0744(2) 0.0189(6) Uani 1 1 d . . . . .
H16A H 0.7673 0.4008 0.0277 0.028 Uiso 1 1 calc GR . . . .
H16B H 0.6304 0.2937 0.0200 0.028 Uiso 1 1 calc GR . . . .
H16C H 0.7703 0.2078 0.1087 0.028 Uiso 1 1 calc GR . . . .
C17 C 0.8221(3) 0.4298(3) 0.2649(2) 0.0135(5) Uani 1 1 d . . . . .
H17A H 0.8952 0.4006 0.2003 0.016 Uiso 1 1 calc R . . . .
H17B H 0.8528 0.3524 0.3457 0.016 Uiso 1 1 calc R . . . .
C18 C 1.0408(4) 0.6718(4) 0.0682(3) 0.0343(9) Uani 1 1 d . . . . .
H18A H 0.9746 0.6287 0.0259 0.052 Uiso 1 1 calc GR . . . .
H18B H 1.1302 0.5891 0.1004 0.052 Uiso 1 1 calc GR . . . .
H18C H 1.0845 0.7736 0.0104 0.052 Uiso 1 1 calc GR . . . .
C19 C 0.9384(3) 0.7085(3) 0.1722(2) 0.0183(6) Uani 1 1 d . . . . .
C20 C 0.9210(4) 0.8439(4) 0.2074(3) 0.0209(6) Uani 1 1 d . . . . .
H20 H 0.9739 0.9426 0.1681 0.025 Uiso 1 1 calc R . . . .
C21 C 0.8105(3) 0.8094(3) 0.3122(2) 0.0153(5) Uani 1 1 d . . . . .
C22 C 0.7472(4) 0.9211(3) 0.3834(3) 0.0208(6) Uani 1 1 d . . . . .
H22A H 0.6327 0.9061 0.4121 0.031 Uiso 1 1 calc GR . . . .
H22B H 0.7584 1.0366 0.3304 0.031 Uiso 1 1 calc GR . . . .
H22C H 0.8091 0.8937 0.4542 0.031 Uiso 1 1 calc GR . . . .
C23 C 0.6703(3) 0.1036(4) 0.7749(3) 0.0183(6) Uani 1 1 d . . . . .
F1 F 0.7809(2) -0.0259(2) 0.80180(15) 0.0251(4) Uani 1 1 d . . . . .
F2 F 0.5423(2) 0.0615(2) 0.85741(15) 0.0274(4) Uani 1 1 d . . . . .
F3 F 0.7277(2) 0.2287(2) 0.78938(16) 0.0321(5) Uani 1 1 d . . . . .
N1 N 0.3860(3) 0.7053(3) 0.45833(19) 0.0152(5) Uani 1 1 d . . . . .
N2 N 0.3202(3) 0.7326(3) 0.56343(19) 0.0132(4) Uani 1 1 d . . . . .
N3 N 0.5315(3) 0.6172(3) 0.6960(2) 0.0122(5) Uani 1 1 d . . . . .
N4 N 0.6510(3) 0.5736(3) 0.61748(19) 0.0125(4) Uani 1 1 d . . . . .
N5 N 0.5385(3) 0.4314(3) 0.3409(2) 0.0137(5) Uani 1 1 d . . . . .
N6 N 0.6573(3) 0.4111(3) 0.25278(19) 0.0124(5) Uani 1 1 d . . . . .
N7 N 0.8426(3) 0.5971(3) 0.25426(19) 0.0137(4) Uani 1 1 d . . . . .
N8 N 0.7640(3) 0.6577(3) 0.34221(19) 0.0140(4) Uani 1 1 d . . . . .
O1 O 0.5026(2) 0.3052(2) 0.60368(16) 0.0160(4) Uani 1 1 d . . . . .
O2 O 0.7677(2) 0.1954(3) 0.54453(18) 0.0271(5) Uani 1 1 d . . . . .
O3 O 0.5443(3) 0.0166(2) 0.62015(17) 0.0227(5) Uani 1 1 d . . . . .
S1 S 0.61586(8) 0.15751(8) 0.61880(6) 0.01446(13) Uani 1 1 d . . . . .
Zn1 Zn 0.58143(3) 0.53414(3) 0.46794(2) 0.01212(7) Uani 1 1 d . . . . .
C24 C 0.1481(3) 0.1560(4) 0.9067(2) 0.0180(6) Uani 1 1 d . . . . .
F4 F -0.0068(2) 0.1262(2) 0.92011(16) 0.0296(4) Uani 1 1 d . . . . .
F5 F 0.1992(2) 0.2033(2) 0.78666(14) 0.0267(4) Uani 1 1 d . . . . .
F6 F 0.2315(2) 0.0130(2) 0.96222(15) 0.0232(4) Uani 1 1 d . . . . .
O4 O 0.1085(2) 0.2447(3) 1.09630(17) 0.0210(4) Uani 1 1 d . . . . .
O5 O 0.0808(2) 0.4571(2) 0.89510(17) 0.0211(4) Uani 1 1 d . . . . .
O6 O 0.3468(2) 0.3238(2) 0.95149(17) 0.0197(4) Uani 1 1 d . . . . .
S2 S 0.17440(8) 0.31343(8) 0.96957(6) 0.01346(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
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.492(4) . ?
C2 C3 1.395(4) . ?
C2 N1 1.339(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.370(4) . ?
C4 C5 1.489(4) . ?
C4 N2 1.349(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 N2 1.452(3) . ?
C6 N3 1.442(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 C8 1.490(4) . ?
C8 C9 1.376(4) . ?
C8 N3 1.349(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.394(4) . ?
C10 C11 1.493(4) . ?
C10 N4 1.334(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 C13 1.497(4) . ?
C13 C14 1.397(4) . ?
C13 N5 1.333(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.370(4) . ?
C15 C16 1.493(3) . ?
C15 N6 1.363(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 N6 1.443(4) . ?
C17 N7 1.445(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 C19 1.496(4) . ?
C19 C20 1.366(4) . ?
C19 N7 1.351(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.394(4) . ?
C21 C22 1.499(4) . ?
C21 N8 1.332(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 F1 1.332(3) . ?
C23 F2 1.333(3) . ?
C23 F3 1.318(3) . ?
C23 S1 1.827(3) . ?
N1 N2 1.366(3) . ?
N1 Zn1 2.047(2) . ?
N3 N4 1.374(3) . ?
N4 Zn1 2.075(2) . ?
N5 N6 1.374(3) . ?
N5 Zn1 2.083(2) . ?
N7 N8 1.373(3) . ?
N8 Zn1 2.080(2) . ?
O1 S1 1.4629(18) . ?
O1 Zn1 2.1671(18) . ?
O2 S1 1.442(2) . ?
O3 S1 1.427(2) . ?
C24 F4 1.333(3) . ?
C24 F5 1.339(3) . ?
C24 F6 1.331(3) . ?
C24 S2 1.821(3) . ?
O4 S2 1.4449(19) . ?
O5 S2 1.4428(19) . ?
O6 S2 1.440(2) . ?

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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 129.0(3) . . ?
N1 C2 C1 121.7(2) . . ?
N1 C2 C3 109.2(2) . . ?
C2 C3 H3 126.4 . . ?
C4 C3 C2 107.2(2) . . ?
C4 C3 H3 126.4 . . ?
C3 C4 C5 131.4(3) . . ?
N2 C4 C3 106.3(2) . . ?
N2 C4 C5 122.4(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
H6A C6 H6B 108.0 . . ?
N2 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
N3 C6 H6A 109.3 . . ?
N3 C6 H6B 109.3 . . ?
N3 C6 N2 111.5(2) . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
C9 C8 C7 131.1(2) . . ?
N3 C8 C7 122.5(2) . . ?
N3 C8 C9 106.4(2) . . ?
C8 C9 H9 126.8 . . ?
C8 C9 C10 106.5(2) . . ?
C10 C9 H9 126.8 . . ?
C9 C10 C11 128.5(2) . . ?
N4 C10 C9 110.3(2) . . ?
N4 C10 C11 121.2(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
C14 C13 C12 128.3(3) . . ?
N5 C13 C12 121.2(2) . . ?
N5 C13 C14 110.5(2) . . ?
C13 C14 H14 126.8 . . ?
C15 C14 C13 106.5(2) . . ?
C15 C14 H14 126.8 . . ?
C14 C15 C16 130.2(3) . . ?
N6 C15 C14 106.6(2) . . ?
N6 C15 C16 123.2(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
H17A C17 H17B 107.9 . . ?
N6 C17 H17A 109.3 . . ?
N6 C17 H17B 109.3 . . ?
N6 C17 N7 111.7(2) . . ?
N7 C17 H17A 109.3 . . ?
N7 C17 H17B 109.3 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
C20 C19 C18 131.6(3) . . ?
N7 C19 C18 121.7(3) . . ?
N7 C19 C20 106.8(2) . . ?
C19 C20 H20 126.6 . . ?
C19 C20 C21 106.8(3) . . ?
C21 C20 H20 126.6 . . ?
C20 C21 C22 127.3(3) . . ?
N8 C21 C20 109.9(2) . . ?
N8 C21 C22 122.8(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
F1 C23 F2 106.9(2) . . ?
F1 C23 S1 110.74(19) . . ?
F2 C23 S1 111.2(2) . . ?
F3 C23 F1 108.8(2) . . ?
F3 C23 F2 107.6(2) . . ?
F3 C23 S1 111.43(19) . . ?
C2 N1 N2 106.0(2) . . ?
C2 N1 Zn1 133.19(18) . . ?
N2 N1 Zn1 118.51(15) . . ?
C4 N2 C6 130.5(2) . . ?
C4 N2 N1 111.3(2) . . ?
N1 N2 C6 118.2(2) . . ?
C8 N3 C6 129.5(2) . . ?
C8 N3 N4 111.4(2) . . ?
N4 N3 C6 118.9(2) . . ?
C10 N4 N3 105.3(2) . . ?
C10 N4 Zn1 136.76(18) . . ?
N3 N4 Zn1 117.80(17) . . ?
C13 N5 N6 105.5(2) . . ?
C13 N5 Zn1 132.60(18) . . ?
N6 N5 Zn1 121.70(18) . . ?
C15 N6 C17 130.0(2) . . ?
C15 N6 N5 110.9(2) . . ?
N5 N6 C17 118.2(2) . . ?
C19 N7 C17 130.0(2) . . ?
C19 N7 N8 110.8(2) . . ?
N8 N7 C17 119.1(2) . . ?
C21 N8 N7 105.8(2) . . ?
C21 N8 Zn1 132.12(17) . . ?
N7 N8 Zn1 121.05(16) . . ?
S1 O1 Zn1 116.25(11) . . ?
O1 S1 C23 102.93(12) . . ?
O2 S1 C23 103.03(13) . . ?
O2 S1 O1 112.15(12) . . ?
O3 S1 C23 104.92(12) . . ?
O3 S1 O1 114.21(12) . . ?
O3 S1 O2 117.46(13) . . ?
N1 Zn1 N4 91.12(9) . . ?
N1 Zn1 N5 101.73(9) . . ?
N1 Zn1 N8 106.26(9) . . ?
N1 Zn1 O1 105.37(8) . . ?
N4 Zn1 N5 164.84(8) . . ?
N4 Zn1 N8 95.63(9) . . ?
N4 Zn1 O1 84.29(8) . . ?
N5 Zn1 O1 84.55(8) . . ?
N8 Zn1 N5 88.54(9) . . ?
N8 Zn1 O1 148.37(7) . . ?
F4 C24 F5 107.9(2) . . ?
F4 C24 S2 111.4(2) . . ?
F5 C24 S2 111.06(19) . . ?
F6 C24 F4 107.3(2) . . ?
F6 C24 F5 107.4(2) . . ?
F6 C24 S2 111.62(19) . . ?
O4 S2 C24 103.27(13) . . ?
O5 S2 C24 102.73(13) . . ?
O5 S2 O4 114.92(12) . . ?
O6 S2 C24 103.44(12) . . ?
O6 S2 O4 114.90(12) . . ?
O6 S2 O5 115.13(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -178.1(3) . . . . ?
C1 C2 N1 N2 178.4(3) . . . . ?
C1 C2 N1 Zn1 16.6(4) . . . . ?
C2 C3 C4 C5 178.4(3) . . . . ?
C2 C3 C4 N2 -1.0(3) . . . . ?
C2 N1 N2 C4 0.4(3) . . . . ?
C2 N1 N2 C6 -180.0(2) . . . . ?
C3 C2 N1 N2 -1.1(3) . . . . ?
C3 C2 N1 Zn1 -162.9(2) . . . . ?
C3 C4 N2 C6 -179.1(3) . . . . ?
C3 C4 N2 N1 0.4(3) . . . . ?
C5 C4 N2 C6 1.4(4) . . . . ?
C5 C4 N2 N1 -179.1(3) . . . . ?
C6 N3 N4 C10 -175.5(2) . . . . ?
C6 N3 N4 Zn1 7.7(3) . . . . ?
C7 C8 C9 C10 178.3(3) . . . . ?
C7 C8 N3 C6 -3.9(4) . . . . ?
C7 C8 N3 N4 -178.4(2) . . . . ?
C8 C9 C10 C11 -178.2(3) . . . . ?
C8 C9 C10 N4 0.3(3) . . . . ?
C8 N3 N4 C10 -0.3(3) . . . . ?
C8 N3 N4 Zn1 -177.14(16) . . . . ?
C9 C8 N3 C6 175.0(3) . . . . ?
C9 C8 N3 N4 0.5(3) . . . . ?
C9 C10 N4 N3 0.0(3) . . . . ?
C9 C10 N4 Zn1 175.89(19) . . . . ?
C11 C10 N4 N3 178.6(2) . . . . ?
C11 C10 N4 Zn1 -5.5(4) . . . . ?
C12 C13 C14 C15 179.4(3) . . . . ?
C12 C13 N5 N6 -179.0(2) . . . . ?
C12 C13 N5 Zn1 -3.9(4) . . . . ?
C13 C14 C15 C16 177.8(3) . . . . ?
C13 C14 C15 N6 -0.5(3) . . . . ?
C13 N5 N6 C15 -0.8(3) . . . . ?
C13 N5 N6 C17 -171.4(2) . . . . ?
C14 C13 N5 N6 0.4(3) . . . . ?
C14 C13 N5 Zn1 175.54(18) . . . . ?
C14 C15 N6 C17 170.0(2) . . . . ?
C14 C15 N6 N5 0.9(3) . . . . ?
C16 C15 N6 C17 -8.5(4) . . . . ?
C16 C15 N6 N5 -177.7(2) . . . . ?
C17 N7 N8 C21 177.3(2) . . . . ?
C17 N7 N8 Zn1 -12.9(3) . . . . ?
C18 C19 C20 C21 -179.2(3) . . . . ?
C18 C19 N7 C17 2.9(5) . . . . ?
C18 C19 N7 N8 178.5(3) . . . . ?
C19 C20 C21 C22 -178.0(3) . . . . ?
C19 C20 C21 N8 1.3(3) . . . . ?
C19 N7 N8 C21 1.0(3) . . . . ?
C19 N7 N8 Zn1 170.91(18) . . . . ?
C20 C19 N7 C17 -175.9(3) . . . . ?
C20 C19 N7 N8 -0.3(3) . . . . ?
C20 C21 N8 N7 -1.4(3) . . . . ?
C20 C21 N8 Zn1 -169.68(19) . . . . ?
C22 C21 N8 N7 177.9(2) . . . . ?
C22 C21 N8 Zn1 9.6(4) . . . . ?
F1 C23 S1 O1 -176.87(19) . . . . ?
F1 C23 S1 O2 -60.1(2) . . . . ?
F1 C23 S1 O3 63.4(2) . . . . ?
F2 C23 S1 O1 64.4(2) . . . . ?
F2 C23 S1 O2 -178.88(19) . . . . ?
F2 C23 S1 O3 -55.4(2) . . . . ?
F3 C23 S1 O1 -55.6(2) . . . . ?
F3 C23 S1 O2 61.1(2) . . . . ?
F3 C23 S1 O3 -175.4(2) . . . . ?
N1 C2 C3 C4 1.4(3) . . . . ?
N2 C6 N3 C8 121.6(3) . . . . ?
N2 C6 N3 N4 -64.3(3) . . . . ?
N3 C6 N2 C4 -111.4(3) . . . . ?
N3 C6 N2 N1 69.1(3) . . . . ?
N3 C8 C9 C10 -0.5(3) . . . . ?
N5 C13 C14 C15 0.1(3) . . . . ?
N6 C17 N7 C19 -119.5(3) . . . . ?
N6 C17 N7 N8 65.2(3) . . . . ?
N7 C17 N6 C15 126.7(3) . . . . ?
N7 C17 N6 N5 -64.8(3) . . . . ?
N7 C19 C20 C21 -0.6(3) . . . . ?
Zn1 N1 N2 C4 165.43(18) . . . . ?
Zn1 N1 N2 C6 -15.0(3) . . . . ?
Zn1 N5 N6 C15 -176.57(16) . . . . ?
Zn1 N5 N6 C17 12.8(3) . . . . ?
Zn1 O1 S1 C23 114.30(13) . . . . ?
Zn1 O1 S1 O2 4.22(16) . . . . ?
Zn1 O1 S1 O3 -132.57(12) . . . . ?
F4 C24 S2 O4 57.7(2) . . . . ?
F4 C24 S2 O5 -62.1(2) . . . . ?
F4 C24 S2 O6 177.77(19) . . . . ?
F5 C24 S2 O4 178.03(19) . . . . ?
F5 C24 S2 O5 58.2(2) . . . . ?
F5 C24 S2 O6 -61.9(2) . . . . ?
F6 C24 S2 O4 -62.2(2) . . . . ?
F6 C24 S2 O5 177.99(19) . . . . ?
F6 C24 S2 O6 57.9(2) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2 2 3 0.0378 2.0000 2.0000 3.0000 -0.2471 -0.0329 0.0215
1 -3 1 0.0892 1.0000 -3.0000 1.0000 0.0052 -0.0835 -0.2983
-1 3 -1 0.0892 -1.0000 3.0000 -1.0000 -0.0052 0.0835 0.2983
1 1 -2 0.0777 1.0000 1.0000 -2.0000 0.0120 -0.1265 0.1575
-3 2 2 0.0871 -3.0000 2.0000 2.0000 -0.0177 0.3179 0.1077
-1 0 1 0.1002 -1.0000 -0.0000 1.0000 -0.0006 0.1079 -0.0331
5 -3 -4 0.0913 5.0000 -3.0000 -4.0000 0.0463 -0.5466 -0.1240
-3 -2 -4 0.0230 -3.0000 -2.0000 -4.0000 0.3240 0.0779 0.0293

_olex2_submission_special_instructions 'No special instructions were received'


###END
_exptl_crystal_description       plate
