# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_2c
_database_code_depnum_ccdc_archive 'CCDC 1503999'
_audit_update_record             
;
2016-09-12 deposited with the CCDC.
2017-01-16 downloaded from the CCDC.
;
_audit_creation_date             2016-09-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H22 N4 O6 Zn'
_chemical_formula_sum            'C10 H22 N4 O6 Zn'
_chemical_formula_weight         359.68
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Zn O6 N3 C10'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.998(5)
_cell_length_b                   8.7997(4)
_cell_length_c                   23.691(8)
_cell_angle_alpha                90
_cell_angle_beta                 148.87(8)
_cell_angle_gamma                90
_cell_volume                     1616(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6229
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.4165
_cell_measurement_theta_min      2.7416
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.550
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            13150
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_min         2.747
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -45.00   46.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.5593   38.0000 -180.0000 91

#__ type_ start__ end____ width___ exp.time_
  2 omega  -99.00  -62.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.5593 -178.0000   90.0000 37

#__ type_ start__ end____ width___ exp.time_
  3 omega  -90.00  -35.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.5593 -178.0000 -120.0000 55

#__ type_ start__ end____ width___ exp.time_
  4 omega  -69.00   27.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.5593   19.0000  120.0000 96

#__ type_ start__ end____ width___ exp.time_
  5 omega   26.00   95.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531   57.0000  120.0000 69

#__ type_ start__ end____ width___ exp.time_
  6 omega   28.00   83.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531   57.0000  -60.0000 55

#__ type_ start__ end____ width___ exp.time_
  7 omega   68.00   95.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531   57.0000  150.0000 27
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0837934000
_diffrn_orient_matrix_UB_12      0.0313360000
_diffrn_orient_matrix_UB_13      0.0424842000
_diffrn_orient_matrix_UB_21      0.0221468000
_diffrn_orient_matrix_UB_22      -0.0588876000
_diffrn_orient_matrix_UB_23      -0.0071303000
_diffrn_orient_matrix_UB_31      -0.0292324000
_diffrn_orient_matrix_UB_32      0.0452793000
_diffrn_orient_matrix_UB_33      -0.0386899000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3332
_reflns_number_total             3720
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_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 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3720
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0226
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0326P)²+0.6435P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0600
_refine_ls_wR_factor_ref         0.0629
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2A(H2AC,H2AD), C2(H2C,H2D)
2.b X=CH2 refined with riding coordinates:
 N2A(H2AA,H2AB), N2(H2A,H2B)
2.c Idealised Me refined as rotating group:
 C5A(H5AA,H5AB,H5AC), C3(H3A,H3B,H3C), C3A(H3AA,H3AB,H3AC), C5(H5A,H5B,H5C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O1A(H1A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.08474(2) 0.25542(2) 0.93232(2) 0.01232(6) Uani 1 1 d . . . . .
O1 O -0.17646(12) 0.14271(12) 0.70903(8) 0.0198(2) Uani 1 1 d . . . . .
H1 H -0.2287 0.2149 0.6964 0.030 Uiso 1 1 calc GR . . . .
O1A O 0.33514(13) 0.14176(11) 1.15219(7) 0.0175(2) Uani 1 1 d . . . . .
H1A H 0.3886 0.2126 1.1651 0.026 Uiso 1 1 calc GR . . . .
O2 O -0.25938(14) 0.40539(12) 0.71596(9) 0.0228(2) Uani 1 1 d . . . . .
O3A O 0.23034(13) 0.42101(11) 0.98336(8) 0.0189(2) Uani 1 1 d . . . . .
N1A N 0.18917(14) 0.10013(13) 1.04004(9) 0.0134(2) Uani 1 1 d . . . . .
N2A N 0.22366(15) -0.12894(13) 1.10578(9) 0.0177(2) Uani 1 1 d . . . . .
H2AA H 0.3174 -0.0963 1.1737 0.021 Uiso 1 1 calc R . . . .
H2AB H 0.1855 -0.2215 1.0915 0.021 Uiso 1 1 calc R . . . .
O2A O 0.46455(14) 0.36047(13) 1.15946(8) 0.0287(3) Uani 1 1 d . . . . .
O3 O -0.09559(13) 0.35358(11) 0.87958(8) 0.0185(2) Uani 1 1 d . . . . .
N2 N 0.02570(16) 0.02116(14) 0.74526(10) 0.0202(3) Uani 1 1 d . . . . .
H2A H -0.0871 0.0175 0.6801 0.024 Uiso 1 1 calc R . . . .
H2B H 0.0931 -0.0214 0.7564 0.024 Uiso 1 1 calc R . . . .
C4A C 0.38694(18) 0.44122(16) 1.08283(11) 0.0174(3) Uani 1 1 d . . . . .
C4 C -0.22293(18) 0.42001(15) 0.78657(12) 0.0170(3) Uani 1 1 d . . . . .
C1 C 0.09446(18) 0.09129(15) 0.82708(11) 0.0145(3) Uani 1 1 d . . . . .
C1A C 0.13938(17) -0.03807(15) 1.02444(10) 0.0133(3) Uani 1 1 d . . . . .
N1 N 0.00403(14) 0.15649(13) 0.81710(9) 0.0142(2) Uani 1 1 d . . . . .
C2A C -0.01986(17) -0.09851(15) 0.90964(11) 0.0154(3) Uani 1 1 d . . . . .
H2AC H -0.0804 -0.0138 0.8578 0.018 Uiso 1 1 calc R . . . .
H2AD H -0.0985 -0.1408 0.8959 0.018 Uiso 1 1 calc R . . . .
C2 C 0.28789(18) 0.09632(17) 0.93667(11) 0.0187(3) Uani 1 1 d . . . . .
H2C H 0.3349 -0.0069 0.9560 0.022 Uiso 1 1 calc R . . . .
H2D H 0.3201 0.1286 0.9927 0.022 Uiso 1 1 calc R . . . .
C5A C 0.4818(2) 0.57126(19) 1.10668(13) 0.0291(4) Uani 1 1 d . . . . .
H5AA H 0.5692 0.5310 1.1281 0.044 Uiso 1 1 calc GR . . . .
H5AB H 0.5380 0.6330 1.1662 0.044 Uiso 1 1 calc GR . . . .
H5AC H 0.3999 0.6342 1.0412 0.044 Uiso 1 1 calc GR . . . .
C3 C 0.3682(2) 0.2057(2) 0.93741(13) 0.0251(3) Uani 1 1 d . . . . .
H3A H 0.3472 0.1680 0.8877 0.038 Uiso 1 1 calc GR . . . .
H3B H 0.4927 0.2126 1.0115 0.038 Uiso 1 1 calc GR . . . .
H3C H 0.3161 0.3065 0.9134 0.038 Uiso 1 1 calc GR . . . .
C3A C 0.0217(2) -0.22211(18) 0.88871(14) 0.0255(3) Uani 1 1 d . . . . .
H3AA H -0.0853 -0.2563 0.8127 0.038 Uiso 1 1 calc GR . . . .
H3AB H 0.0771 -0.3082 0.9377 0.038 Uiso 1 1 calc GR . . . .
H3AC H 0.0997 -0.1809 0.9023 0.038 Uiso 1 1 calc GR . . . .
C5 C -0.3305(2) 0.52204(18) 0.76533(14) 0.0263(3) Uani 1 1 d . . . . .
H5A H -0.2630 0.6118 0.8125 0.039 Uiso 1 1 calc GR . . . .
H5B H -0.3644 0.4667 0.7811 0.039 Uiso 1 1 calc GR . . . .
H5C H -0.4339 0.5539 0.6887 0.039 Uiso 1 1 calc GR . . . .


_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 O3A 1.9579(15) . ?
Zn1 N1A 1.9975(19) . ?
Zn1 O3 1.9587(18) . ?
Zn1 N1 2.0043(18) . ?
O1 H1 0.8400 . ?
O1 N1 1.425(4) . ?
O1A H1A 0.8400 . ?
O1A N1A 1.424(3) . ?
O2 C4 1.2441(19) . ?
O3A C4A 1.275(4) . ?
N1A C1A 1.3042(18) . ?
N2A H2AA 0.8800 . ?
N2A H2AB 0.8800 . ?
N2A C1A 1.334(2) . ?
O2A C4A 1.240(2) . ?
O3 C4 1.281(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C1 1.334(2) . ?
C4A C5A 1.509(2) . ?
C4 C5 1.507(2) . ?
C1 N1 1.2945(18) . ?
C1 C2 1.505(4) . ?
C1A C2A 1.504(4) . ?
C2A H2AC 0.9900 . ?
C2A H2AD 0.9900 . ?
C2A C3A 1.531(2) . ?
C2 H2C 0.9900 . ?
C2 H2D 0.9900 . ?
C2 C3 1.530(2) . ?
C5A H5AA 0.9800 . ?
C5A H5AB 0.9800 . ?
C5A H5AC 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C3A H3AA 0.9800 . ?
C3A H3AB 0.9800 . ?
C3A H3AC 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?

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
O3A Zn1 N1A 118.68(14) . . ?
O3A Zn1 O3 105.47(7) . . ?
O3A Zn1 N1 102.61(8) . . ?
N1A Zn1 N1 109.98(8) . . ?
O3 Zn1 N1A 105.14(9) . . ?
O3 Zn1 N1 115.36(15) . . ?
N1 O1 H1 109.5 . . ?
N1A O1A H1A 109.5 . . ?
C4A O3A Zn1 124.15(10) . . ?
O1A N1A Zn1 118.65(11) . . ?
C1A N1A Zn1 130.04(13) . . ?
C1A N1A O1A 111.19(11) . . ?
H2AA N2A H2AB 120.0 . . ?
C1A N2A H2AA 120.0 . . ?
C1A N2A H2AB 120.0 . . ?
C4 O3 Zn1 120.67(12) . . ?
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
O3A C4A C5A 116.91(13) . . ?
O2A C4A O3A 124.15(16) . . ?
O2A C4A C5A 118.94(18) . . ?
O2 C4 O3 123.91(14) . . ?
O2 C4 C5 119.98(17) . . ?
O3 C4 C5 116.10(14) . . ?
N2 C1 C2 118.13(16) . . ?
N1 C1 N2 123.63(18) . . ?
N1 C1 C2 118.24(13) . . ?
N1A C1A N2A 123.01(16) . . ?
N1A C1A C2A 118.67(12) . . ?
N2A C1A C2A 118.32(16) . . ?
O1 N1 Zn1 119.17(12) . . ?
C1 N1 Zn1 128.82(15) . . ?
C1 N1 O1 111.85(12) . . ?
C1A C2A H2AC 109.1 . . ?
C1A C2A H2AD 109.1 . . ?
C1A C2A C3A 112.34(14) . . ?
H2AC C2A H2AD 107.9 . . ?
C3A C2A H2AC 109.1 . . ?
C3A C2A H2AD 109.1 . . ?
C1 C2 H2C 109.2 . . ?
C1 C2 H2D 109.2 . . ?
C1 C2 C3 111.98(12) . . ?
H2C C2 H2D 107.9 . . ?
C3 C2 H2C 109.2 . . ?
C3 C2 H2D 109.2 . . ?
C4A C5A H5AA 109.5 . . ?
C4A C5A H5AB 109.5 . . ?
C4A C5A H5AC 109.5 . . ?
H5AA C5A H5AB 109.5 . . ?
H5AA C5A H5AC 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2A C3A H3AA 109.5 . . ?
C2A C3A H3AB 109.5 . . ?
C2A C3A H3AC 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
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 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 1504000'
_audit_update_record             
;
2016-09-12 deposited with the CCDC.
2017-01-16 downloaded from the CCDC.
;
_audit_creation_date             2016-09-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 Cl2 N4 O6 Zn'
_chemical_formula_sum            'C18 H20 Cl2 N4 O6 Zn'
_chemical_formula_weight         524.65
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Zn Cl2 N4 C18'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   32.7550(17)
_cell_length_b                   10.5714(5)
_cell_length_c                   13.5063(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.305(4)
_cell_angle_gamma                90
_cell_volume                     4386.2(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5486
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.0849
_cell_measurement_theta_min      2.7289
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.406
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18244
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.735
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -91.00  -65.00   1.0000    8.1200
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -57.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -98.00  -32.00   1.0000    8.1200
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  178.0000  -30.0000 66

#__ type_ start__ end____ width___ exp.time_
  3 omega  -60.00   51.00   1.0000    8.1200
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   19.0000   30.0000 111

#__ type_ start__ end____ width___ exp.time_
  4 omega   -5.00   36.00   1.0000    8.1200
omega____ theta____ kappa____ phi______ frames
    -       23.3616 -106.0000  163.0000 41

#__ type_ start__ end____ width___ exp.time_
  5 omega   -7.00   93.00   1.0000    8.1200
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000 -120.0000 100

#__ type_ start__ end____ width___ exp.time_
  6 omega  -25.00    3.00   1.0000    8.1200
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000  120.0000 28

#__ type_ start__ end____ width___ exp.time_
  7 omega   36.00   65.00   1.0000    8.1200
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000  120.0000 29

#__ type_ start__ end____ width___ exp.time_
  8 omega   26.00   51.00   1.0000    8.1200
omega____ theta____ kappa____ phi______ frames
    -       23.3616 -106.0000  -16.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0165245000
_diffrn_orient_matrix_UB_12      0.0084588000
_diffrn_orient_matrix_UB_13      0.0384835000
_diffrn_orient_matrix_UB_21      0.0676275000
_diffrn_orient_matrix_UB_22      -0.0024905000
_diffrn_orient_matrix_UB_23      0.0228535000
_diffrn_orient_matrix_UB_31      0.0136878000
_diffrn_orient_matrix_UB_32      0.0552969000
_diffrn_orient_matrix_UB_33      0.0113675000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4459
_reflns_number_total             5042
_reflns_odcompleteness_completeness 99.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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         1.535
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         5042
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.080
_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)+(0.0406P)²+16.9329P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1039
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C4A(H4A), C6A(H6A), C6(H6), C4(H4), C7(H7), C5A(H5A), C5(H5)
2.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N2A(H2AA,H2AB)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C9A(H9AA,H9AB,H9AC)
2.d Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 0.11677(2) 0.87537(3) 0.20081(2) 0.01368(9) Uani 1 1 d . . . . .
Cl1 Cl 0.17401(2) 0.67890(7) 0.47816(6) 0.02231(16) Uani 1 1 d . . . . .
Cl1A Cl 0.13109(3) 0.61001(7) -0.06474(6) 0.02966(18) Uani 1 1 d . . . . .
O3 O 0.07827(6) 0.8541(2) 0.05448(15) 0.0203(4) Uani 1 1 d . . . . .
O1A O 0.21164(6) 0.80430(18) 0.26413(16) 0.0192(4) Uani 1 1 d . . . . .
H1A H 0.2121 0.8818 0.2666 0.029 Uiso 1 1 calc GR . . . .
O3A O 0.13109(6) 1.05595(18) 0.19820(15) 0.0177(4) Uani 1 1 d . . . . .
O2 O 0.01407(6) 0.8198(2) 0.07269(16) 0.0270(5) Uani 1 1 d . . . . .
O1 O 0.04605(6) 0.7920(2) 0.27983(15) 0.0232(5) Uani 1 1 d . . . . .
H1 H 0.0338 0.7974 0.2158 0.035 Uiso 1 1 calc GR . . . .
O2A O 0.20385(6) 1.04859(18) 0.27170(16) 0.0191(4) Uani 1 1 d . . . . .
N2 N 0.08051(7) 0.8574(2) 0.47343(18) 0.0168(5) Uani 1 1 d . . . . .
H2A H 0.0548 0.8255 0.4500 0.020 Uiso 1 1 calc R . . . .
H2B H 0.0920 0.8779 0.5389 0.020 Uiso 1 1 calc R . . . .
N1A N 0.16833(7) 0.7623(2) 0.21438(17) 0.0144(4) Uani 1 1 d . . . . .
N1 N 0.08815(7) 0.8473(2) 0.30849(18) 0.0167(5) Uani 1 1 d . . . . .
N2A N 0.20290(8) 0.5836(2) 0.1796(2) 0.0251(6) Uani 1 1 d . . . . .
H2AA H 0.2284 0.6157 0.2091 0.030 Uiso 1 1 calc R . . . .
H2AB H 0.2002 0.5091 0.1525 0.030 Uiso 1 1 calc R . . . .
C8 C 0.03720(9) 0.8386(3) 0.0182(2) 0.0172(5) Uani 1 1 d . . . . .
C7A C 0.10152(9) 0.5498(3) 0.1944(2) 0.0219(6) Uani 1 1 d . . . . .
H7A H 0.1114 0.5748 0.2648 0.026 Uiso 1 1 calc R . . . .
C3 C 0.18320(9) 0.8424(3) 0.4923(2) 0.0157(5) Uani 1 1 d . . . . .
C8A C 0.16882(9) 1.1072(3) 0.2351(2) 0.0158(5) Uani 1 1 d . . . . .
C4A C 0.06999(10) 0.4780(3) -0.0165(2) 0.0268(7) Uani 1 1 d . . . . .
H4A H 0.0594 0.4551 -0.0873 0.032 Uiso 1 1 calc R . . . .
C3A C 0.10701(10) 0.5519(3) 0.0227(2) 0.0214(6) Uani 1 1 d . . . . .
C1A C 0.16741(9) 0.6497(3) 0.1758(2) 0.0161(5) Uani 1 1 d . . . . .
C6A C 0.06402(10) 0.4773(3) 0.1556(3) 0.0275(7) Uani 1 1 d . . . . .
H6A H 0.0489 0.4543 0.1997 0.033 Uiso 1 1 calc R . . . .
C1 C 0.10263(8) 0.8751(2) 0.4081(2) 0.0141(5) Uani 1 1 d . . . . .
C6 C 0.19775(9) 1.1008(3) 0.5150(2) 0.0202(6) Uani 1 1 d . . . . .
H6 H 0.2028 1.1875 0.5221 0.024 Uiso 1 1 calc R . . . .
C4 C 0.22534(9) 0.8870(3) 0.5422(2) 0.0210(6) Uani 1 1 d . . . . .
H4 H 0.2484 0.8308 0.5685 0.025 Uiso 1 1 calc R . . . .
C9 C 0.01644(10) 0.8430(3) -0.1013(2) 0.0277(7) Uani 1 1 d . . . . .
H9A H 0.0202 0.9258 -0.1261 0.042 Uiso 1 1 calc GR . . . .
H9B H -0.0141 0.8246 -0.1215 0.042 Uiso 1 1 calc GR . . . .
H9C H 0.0300 0.7815 -0.1320 0.042 Uiso 1 1 calc GR . . . .
C7 C 0.15567(9) 1.0549(3) 0.4671(2) 0.0168(5) Uani 1 1 d . . . . .
H7 H 0.1325 1.1111 0.4435 0.020 Uiso 1 1 calc R . . . .
C2 C 0.14805(8) 0.9253(3) 0.4544(2) 0.0139(5) Uani 1 1 d . . . . .
C5A C 0.04906(10) 0.4389(3) 0.0508(3) 0.0280(7) Uani 1 1 d . . . . .
H5A H 0.0248 0.3866 0.0258 0.034 Uiso 1 1 calc R . . . .
C2A C 0.12442(9) 0.5854(3) 0.1296(2) 0.0167(5) Uani 1 1 d . . . . .
C9A C 0.16989(10) 1.2502(3) 0.2340(2) 0.0239(6) Uani 1 1 d . . . . .
H9AA H 0.1461 1.2811 0.1747 0.036 Uiso 1 1 calc GR . . . .
H9AB H 0.1969 1.2782 0.2283 0.036 Uiso 1 1 calc GR . . . .
H9AC H 0.1674 1.2822 0.2981 0.036 Uiso 1 1 calc GR . . . .
C5 C 0.23233(9) 1.0157(3) 0.5522(2) 0.0216(6) Uani 1 1 d . . . . .
H5 H 0.2605 1.0463 0.5842 0.026 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O3 1.9538(19) . ?
Zn1 O3A 1.969(2) . ?
Zn1 N1A 2.025(2) . ?
Zn1 N1 2.007(2) . ?
Cl1 C3 1.754(3) . ?
Cl1A C3A 1.744(3) . ?
O3 C8 1.272(3) . ?
O1A H1A 0.8200 . ?
O1A N1A 1.414(3) . ?
O3A C8A 1.282(3) . ?
O2 C8 1.242(4) . ?
O1 H1 0.8200 . ?
O1 N1 1.422(3) . ?
O2A C8A 1.245(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C1 1.335(4) . ?
N1A C1A 1.296(4) . ?
N1 C1 1.296(3) . ?
N2A H2AA 0.8600 . ?
N2A H2AB 0.8600 . ?
N2A C1A 1.342(4) . ?
C8 C9 1.519(4) . ?
C7A H7A 0.9300 . ?
C7A C6A 1.387(4) . ?
C7A C2A 1.388(4) . ?
C3 C4 1.391(4) . ?
C3 C2 1.395(4) . ?
C8A C9A 1.512(4) . ?
C4A H4A 0.9300 . ?
C4A C3A 1.384(4) . ?
C4A C5A 1.377(5) . ?
C3A C2A 1.401(4) . ?
C1A C2A 1.492(4) . ?
C6A H6A 0.9300 . ?
C6A C5A 1.388(5) . ?
C1 C2 1.497(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.391(4) . ?
C6 C5 1.397(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C7 H7 0.9300 . ?
C7 C2 1.392(4) . ?
C5A H5A 0.9300 . ?
C9A H9AA 0.9600 . ?
C9A H9AB 0.9600 . ?
C9A H9AC 0.9600 . ?
C5 H5 0.9300 . ?

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
O3 Zn1 O3A 99.65(8) . . ?
O3 Zn1 N1A 104.42(9) . . ?
O3 Zn1 N1 114.59(9) . . ?
O3A Zn1 N1A 112.18(8) . . ?
O3A Zn1 N1 109.28(9) . . ?
N1 Zn1 N1A 115.59(9) . . ?
C8 O3 Zn1 129.02(19) . . ?
N1A O1A H1A 109.5 . . ?
C8A O3A Zn1 127.35(18) . . ?
N1 O1 H1 109.5 . . ?
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
O1A N1A Zn1 121.71(16) . . ?
C1A N1A Zn1 127.13(18) . . ?
C1A N1A O1A 111.0(2) . . ?
O1 N1 Zn1 121.07(16) . . ?
C1 N1 Zn1 128.64(18) . . ?
C1 N1 O1 110.3(2) . . ?
H2AA N2A H2AB 120.0 . . ?
C1A N2A H2AA 120.0 . . ?
C1A N2A H2AB 120.0 . . ?
O3 C8 C9 115.4(3) . . ?
O2 C8 O3 125.0(3) . . ?
O2 C8 C9 119.6(3) . . ?
C6A C7A H7A 119.6 . . ?
C6A C7A C2A 120.8(3) . . ?
C2A C7A H7A 119.6 . . ?
C4 C3 Cl1 119.4(2) . . ?
C4 C3 C2 121.2(3) . . ?
C2 C3 Cl1 119.4(2) . . ?
O3A C8A C9A 116.2(2) . . ?
O2A C8A O3A 125.1(2) . . ?
O2A C8A C9A 118.7(2) . . ?
C3A C4A H4A 120.4 . . ?
C5A C4A H4A 120.4 . . ?
C5A C4A C3A 119.2(3) . . ?
C4A C3A Cl1A 118.8(2) . . ?
C4A C3A C2A 121.8(3) . . ?
C2A C3A Cl1A 119.4(2) . . ?
N1A C1A N2A 124.4(3) . . ?
N1A C1A C2A 118.3(2) . . ?
N2A C1A C2A 117.3(2) . . ?
C7A C6A H6A 120.0 . . ?
C7A C6A C5A 120.0(3) . . ?
C5A C6A H6A 120.0 . . ?
N2 C1 C2 117.6(2) . . ?
N1 C1 N2 124.6(2) . . ?
N1 C1 C2 117.8(2) . . ?
C7 C6 H6 120.3 . . ?
C7 C6 C5 119.4(3) . . ?
C5 C6 H6 120.3 . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4 120.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C2 120.5(3) . . ?
C2 C7 H7 119.8 . . ?
C3 C2 C1 120.3(2) . . ?
C7 C2 C3 118.9(2) . . ?
C7 C2 C1 120.7(2) . . ?
C4A C5A C6A 120.3(3) . . ?
C4A C5A H5A 119.8 . . ?
C6A C5A H5A 119.8 . . ?
C7A C2A C3A 117.7(3) . . ?
C7A C2A C1A 119.9(2) . . ?
C3A C2A C1A 122.3(3) . . ?
C8A C9A H9AA 109.5 . . ?
C8A C9A H9AB 109.5 . . ?
C8A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?

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
Zn1 O3 C8 O2 -8.6(4) . . . . ?
Zn1 O3 C8 C9 172.0(2) . . . . ?
Zn1 O3A C8A O2A 6.5(4) . . . . ?
Zn1 O3A C8A C9A -173.03(18) . . . . ?
Zn1 N1A C1A N2A 173.9(2) . . . . ?
Zn1 N1A C1A C2A -9.9(4) . . . . ?
Zn1 N1 C1 N2 177.2(2) . . . . ?
Zn1 N1 C1 C2 -5.6(4) . . . . ?
Cl1 C3 C4 C5 179.5(2) . . . . ?
Cl1 C3 C2 C1 3.7(3) . . . . ?
Cl1 C3 C2 C7 179.3(2) . . . . ?
Cl1A C3A C2A C7A 172.6(2) . . . . ?
Cl1A C3A C2A C1A -11.4(4) . . . . ?
O1A N1A C1A N2A -2.1(4) . . . . ?
O1A N1A C1A C2A 174.1(2) . . . . ?
O1 N1 C1 N2 -1.8(4) . . . . ?
O1 N1 C1 C2 175.4(2) . . . . ?
N2 C1 C2 C3 90.3(3) . . . . ?
N2 C1 C2 C7 -85.1(3) . . . . ?
N1A C1A C2A C7A -67.0(4) . . . . ?
N1A C1A C2A C3A 117.0(3) . . . . ?
N1 C1 C2 C3 -87.1(3) . . . . ?
N1 C1 C2 C7 97.5(3) . . . . ?
N2A C1A C2A C7A 109.5(3) . . . . ?
N2A C1A C2A C3A -66.5(4) . . . . ?
C7A C6A C5A C4A -3.4(5) . . . . ?
C3 C4 C5 C6 1.3(4) . . . . ?
C4A C3A C2A C7A -4.5(4) . . . . ?
C4A C3A C2A C1A 171.5(3) . . . . ?
C3A C4A C5A C6A 2.4(5) . . . . ?
C6A C7A C2A C3A 3.6(4) . . . . ?
C6A C7A C2A C1A -172.5(3) . . . . ?
C6 C7 C2 C3 1.3(4) . . . . ?
C6 C7 C2 C1 176.8(2) . . . . ?
C4 C3 C2 C1 -175.5(3) . . . . ?
C4 C3 C2 C7 0.1(4) . . . . ?
C7 C6 C5 C4 0.0(4) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
C5A C4A C3A Cl1A -175.6(2) . . . . ?
C5A C4A C3A C2A 1.6(5) . . . . ?
C2A C7A C6A C5A 0.3(5) . . . . ?
C5 C6 C7 C2 -1.3(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_4b_OTf2
_database_code_depnum_ccdc_archive 'CCDC 1504001'
_audit_update_record             
;
2016-09-12 deposited with the CCDC.
2017-01-16 downloaded from the CCDC.
;
_audit_creation_date             2016-09-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H32 Cl2 N8 O3 Zn, 2(C F3 O3 S)'
_chemical_formula_sum            'C24 H32 Cl2 F6 N8 O9 S2 Zn'
_chemical_formula_weight         890.96
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Zn S F3 C22 H21 N O3'
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'
Cl Cl 0.1484 0.1585 '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           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                   8.7052(5)
_cell_length_b                   12.9506(6)
_cell_length_c                   17.0474(7)
_cell_angle_alpha                108.023(4)
_cell_angle_beta                 90.814(4)
_cell_angle_gamma                95.484(4)
_cell_volume                     1817.27(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6106
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.9120
_cell_measurement_theta_min      3.1740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.027
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16514
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.616
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -99.00  -72.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.4031  178.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -77.00  -36.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.4031  119.0000   66.0000 41

#__ type_ start__ end____ width___ exp.time_
  3 omega   35.00   92.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4968  178.0000  -90.0000 57

#__ type_ start__ end____ width___ exp.time_
  4 omega   -7.00   78.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4968 -119.0000  -18.0000 85

#__ type_ start__ end____ width___ exp.time_
  5 omega    5.00   91.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4968   77.0000 -120.0000 86

#__ type_ start__ end____ width___ exp.time_
  6 omega   10.00   97.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4968   38.0000  150.0000 87

#__ type_ start__ end____ width___ exp.time_
  7 omega    5.00   96.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4968   38.0000   60.0000 91
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0256047000
_diffrn_orient_matrix_UB_12      0.0352617000
_diffrn_orient_matrix_UB_13      0.0398010000
_diffrn_orient_matrix_UB_21      -0.0248913000
_diffrn_orient_matrix_UB_22      -0.0415946000
_diffrn_orient_matrix_UB_23      0.0173752000
_diffrn_orient_matrix_UB_31      0.0737519000
_diffrn_orient_matrix_UB_32      -0.0195155000
_diffrn_orient_matrix_UB_33      -0.0057031000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6629
_reflns_number_total             8351
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.98
_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 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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         2.589
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         8351
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0509
_refine_ls_restrained_S_all      1.045
_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)+(0.0519P)²+4.4074P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1342
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H3AA,H3AB,H3AC} of C3A, {H4A,H4B,H4C} of C4, All C(H,H)
  groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups, {H12A,H12B,H12C} of C12, {H4AA,H4AB,H4AC} of C4A, {H3B,H3C,
  H3D} of C3
2. Restrained distances
 O2-H2
 0.85 with sigma of 0.01
 C11-H2
 1.897194 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
3.b Aromatic/amide H refined with riding coordinates:
 N3(H3), N3A(H3A), C8(H8), C9(H9), C10(H10), C7A(H7A), C7(H7), C10A(H10A),
 C9A(H9A), C8A(H8A)
3.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N2A(H2AA,H2AB)
3.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C3A(H3AA,H3AB,H3AC), C3(H3B,H3C,H3D), C4A(H4AA,H4AB,H4AC),
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 0.48136(4) 0.72133(3) 0.15761(2) 0.02416(11) Uani 1 1 d . . . . .
S2 S 0.99154(9) 0.81942(6) 0.53595(5) 0.01947(16) Uani 1 1 d . . . . .
Cl1 Cl 0.17148(10) 0.91872(7) 0.11345(5) 0.02780(18) Uani 1 1 d . . . . .
S1 S 0.36871(10) 0.68397(7) -0.05636(5) 0.02550(18) Uani 1 1 d . . . . .
Cl1A Cl 0.42164(11) 0.84668(10) 0.46357(6) 0.0416(2) Uani 1 1 d . . . . .
O4 O 0.4464(3) 0.7889(2) -0.05249(15) 0.0275(5) Uani 1 1 d . . . . .
N3 N 0.3760(3) 0.5913(2) 0.17754(17) 0.0210(5) Uani 1 1 d . . . . .
H3 H 0.4074 0.5270 0.1530 0.025 Uiso 1 1 calc R . . . .
O3 O 0.3294(3) 0.6709(2) 0.02272(15) 0.0317(6) Uani 1 1 d . . . . .
F3 F 0.0954(3) 0.5848(2) -0.11548(17) 0.0533(7) Uani 1 1 d . . . . .
O7 O 1.1277(3) 0.8694(2) 0.58770(15) 0.0301(5) Uani 1 1 d . . . . .
O6 O 1.0149(3) 0.76663(19) 0.45002(14) 0.0275(5) Uani 1 1 d . . . . .
O1 O 0.2051(3) 0.69587(17) 0.26026(13) 0.0206(4) Uani 1 1 d . . . . .
F7 F 0.7969(3) 0.6505(2) 0.53408(16) 0.0580(8) Uani 1 1 d . . . . .
N2 N 0.1366(3) 0.8903(2) 0.33552(17) 0.0240(6) Uani 1 1 d . . . . .
H2A H 0.0898 0.8339 0.3473 0.029 Uiso 1 1 calc R . . . .
H2B H 0.1134 0.9566 0.3614 0.029 Uiso 1 1 calc R . . . .
F5 F 0.0972(3) 0.75784(19) -0.06218(15) 0.0399(5) Uani 1 1 d . . . . .
N3A N 0.5756(3) 0.8427(2) 0.12256(16) 0.0196(5) Uani 1 1 d . . . . .
H3A H 0.5422 0.8516 0.0764 0.023 Uiso 1 1 calc R . . . .
N4A N 0.7768(3) 0.9868(2) 0.14787(16) 0.0221(6) Uani 1 1 d . . . . .
N1 N 0.2882(3) 0.7826(2) 0.23566(16) 0.0200(5) Uani 1 1 d . . . . .
F6 F 0.8968(3) 0.7426(2) 0.65419(14) 0.0486(6) Uani 1 1 d . . . . .
C4 C 0.2313(4) 0.4066(3) 0.2148(2) 0.0288(7) Uani 1 1 d . . . . .
H4A H 0.2355 0.3868 0.1546 0.035 Uiso 1 1 calc GR . . . .
H4B H 0.1559 0.3549 0.2292 0.035 Uiso 1 1 calc GR . . . .
H4C H 0.3334 0.4041 0.2387 0.035 Uiso 1 1 calc GR . . . .
O8 O 0.8632(3) 0.8861(2) 0.55066(14) 0.0293(5) Uani 1 1 d . . . . .
F8 F 1.0328(4) 0.6372(2) 0.56545(19) 0.0616(8) Uani 1 1 d . . . . .
N4 N 0.1851(3) 0.5168(2) 0.24756(17) 0.0225(6) Uani 1 1 d . . . . .
N1A N 0.6471(3) 0.8101(2) 0.25887(17) 0.0243(6) Uani 1 1 d . . . . .
O1A O 0.7258(3) 0.90467(18) 0.24370(13) 0.0215(5) Uani 1 1 d . . . . .
C2 C 0.2621(3) 0.5981(2) 0.22568(18) 0.0182(6) Uani 1 1 d . . . . .
F4 F 0.1935(3) 0.6932(2) -0.18048(14) 0.0473(6) Uani 1 1 d . . . . .
C3A C 0.8795(4) 1.0695(3) 0.2099(2) 0.0269(7) Uani 1 1 d . . . . .
H3AA H 0.9588 1.1025 0.1821 0.032 Uiso 1 1 calc GR . . . .
H3AB H 0.9293 1.0350 0.2458 0.032 Uiso 1 1 calc GR . . . .
H3AC H 0.8192 1.1262 0.2431 0.032 Uiso 1 1 calc GR . . . .
C2A C 0.6867(3) 0.9097(3) 0.16721(18) 0.0181(6) Uani 1 1 d . . . . .
C8 C 0.4773(4) 1.1631(3) 0.2433(2) 0.0281(7) Uani 1 1 d . . . . .
H8 H 0.5304 1.2270 0.2362 0.034 Uiso 1 1 calc R . . . .
C9 C 0.5032(4) 1.1367(3) 0.3153(2) 0.0290(7) Uani 1 1 d . . . . .
H9 H 0.5740 1.1827 0.3575 0.035 Uiso 1 1 calc R . . . .
C6 C 0.2979(4) 1.0026(3) 0.19213(19) 0.0203(6) Uani 1 1 d . . . . .
C10 C 0.4260(4) 1.0438(3) 0.3255(2) 0.0252(7) Uani 1 1 d . . . . .
H10 H 0.4436 1.0268 0.3751 0.030 Uiso 1 1 calc R . . . .
O5 O 0.4282(4) 0.5905(2) -0.11275(18) 0.0447(7) Uani 1 1 d . . . . .
C5 C 0.3223(4) 0.9743(2) 0.26407(19) 0.0190(6) Uani 1 1 d . . . . .
C6A C 0.4984(4) 0.7258(4) 0.4169(2) 0.0350(9) Uani 1 1 d . . . . .
C1A C 0.6719(4) 0.8193(3) 0.3367(2) 0.0229(7) Uani 1 1 d . . . . .
O2 O 0.6455(4) 0.6117(2) 0.0841(2) 0.0474(8) Uani 1 1 d D . . . .
H2 H 0.636(4) 0.5473(19) 0.088(3) 0.071 Uiso 1 1 d DR . . . .
C7A C 0.4424(5) 0.6314(4) 0.4368(2) 0.0460(12) Uani 1 1 d . . . . .
H7A H 0.3659 0.6350 0.4765 0.055 Uiso 1 1 calc R . . . .
C1 C 0.2428(3) 0.8751(3) 0.27838(18) 0.0187(6) Uani 1 1 d . . . . .
C13 C 0.1795(5) 0.6807(3) -0.1055(2) 0.0327(8) Uani 1 1 d . . . . .
C14 C 0.9256(5) 0.7063(3) 0.5739(2) 0.0340(8) Uani 1 1 d . . . . .
C7 C 0.3739(4) 1.0959(3) 0.1818(2) 0.0255(7) Uani 1 1 d . . . . .
H7 H 0.3554 1.1139 0.1327 0.031 Uiso 1 1 calc R . . . .
N2A N 0.7473(3) 0.9041(2) 0.39345(17) 0.0271(6) Uani 1 1 d . . . . .
H2AA H 0.7860 0.9613 0.3799 0.033 Uiso 1 1 calc R . . . .
H2AB H 0.7587 0.9033 0.4446 0.033 Uiso 1 1 calc R . . . .
C3 C 0.0739(4) 0.5358(3) 0.3125(2) 0.0314(8) Uani 1 1 d . . . . .
H3B H -0.0200 0.4854 0.2929 0.047 Uiso 1 1 calc GR . . . .
H3C H 0.0479 0.6112 0.3266 0.047 Uiso 1 1 calc GR . . . .
H3D H 0.1190 0.5237 0.3615 0.047 Uiso 1 1 calc GR . . . .
C5A C 0.6097(4) 0.7220(3) 0.3597(2) 0.0280(7) Uani 1 1 d . . . . .
C10A C 0.6660(5) 0.6195(3) 0.3198(3) 0.0416(10) Uani 1 1 d . . . . .
H10A H 0.7416 0.6144 0.2795 0.050 Uiso 1 1 calc R . . . .
C4A C 0.7535(4) 1.0000(3) 0.0663(2) 0.0279(7) Uani 1 1 d . . . . .
H4AA H 0.6615 1.0378 0.0657 0.042 Uiso 1 1 calc GR . . . .
H4AB H 0.7396 0.9280 0.0243 0.042 Uiso 1 1 calc GR . . . .
H4AC H 0.8439 1.0430 0.0545 0.042 Uiso 1 1 calc GR . . . .
C9A C 0.6102(6) 0.5275(4) 0.3400(3) 0.0458(11) Uani 1 1 d . . . . .
H9A H 0.6480 0.4593 0.3138 0.055 Uiso 1 1 calc R . . . .
C8A C 0.4998(6) 0.5350(4) 0.3982(3) 0.0496(12) Uani 1 1 d . . . . .
H8A H 0.4627 0.4714 0.4117 0.059 Uiso 1 1 calc R . . . .
C11 C 0.7879(5) 0.6301(4) 0.0477(3) 0.0526(12) Uani 1 1 d D . . . .
H11A H 0.7776 0.6856 0.0196 0.063 Uiso 1 1 calc R . . . .
H11B H 0.8083 0.5615 0.0052 0.063 Uiso 1 1 calc R . . . .
C12 C 0.9255(6) 0.6683(4) 0.1095(3) 0.0534(12) Uani 1 1 d . . . . .
H12A H 1.0200 0.6754 0.0801 0.080 Uiso 1 1 calc GR . . . .
H12B H 0.9349 0.6149 0.1388 0.080 Uiso 1 1 calc GR . . . .
H12C H 0.9103 0.7392 0.1492 0.080 Uiso 1 1 calc GR . . . .


_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 N3 1.965(3) . ?
Zn1 N3A 1.961(3) . ?
Zn1 N1 2.212(3) . ?
Zn1 N1A 2.183(3) . ?
Zn1 O2 2.228(3) . ?
S2 O7 1.440(2) . ?
S2 O6 1.439(2) . ?
S2 O8 1.454(2) . ?
S2 C14 1.825(4) . ?
Cl1 C6 1.737(3) . ?
S1 O4 1.441(2) . ?
S1 O3 1.451(3) . ?
S1 O5 1.439(3) . ?
S1 C13 1.828(4) . ?
Cl1A C6A 1.724(5) . ?
N3 H3 0.8800 . ?
N3 C2 1.288(4) . ?
F3 C13 1.342(4) . ?
O1 N1 1.451(3) . ?
O1 C2 1.366(4) . ?
F7 C14 1.326(4) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C1 1.336(4) . ?
F5 C13 1.324(5) . ?
N3A H3A 0.8800 . ?
N3A C2A 1.296(4) . ?
N4A C3A 1.468(4) . ?
N4A C2A 1.335(4) . ?
N4A C4A 1.466(4) . ?
N1 C1 1.296(4) . ?
F6 C14 1.338(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 N4 1.460(4) . ?
F8 C14 1.333(5) . ?
N4 C2 1.346(4) . ?
N4 C3 1.459(4) . ?
N1A O1A 1.442(3) . ?
N1A C1A 1.309(4) . ?
O1A C2A 1.366(4) . ?
F4 C13 1.343(4) . ?
C3A H3AA 0.9800 . ?
C3A H3AB 0.9800 . ?
C3A H3AC 0.9800 . ?
C8 H8 0.9500 . ?
C8 C9 1.394(5) . ?
C8 C7 1.388(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.382(5) . ?
C6 C5 1.403(4) . ?
C6 C7 1.382(5) . ?
C10 H10 0.9500 . ?
C10 C5 1.398(5) . ?
C5 C1 1.490(4) . ?
C6A C7A 1.412(6) . ?
C6A C5A 1.378(5) . ?
C1A N2A 1.327(4) . ?
C1A C5A 1.488(5) . ?
O2 H2 0.855(10) . ?
O2 C11 1.427(5) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.365(7) . ?
C7 H7 0.9500 . ?
N2A H2AA 0.8800 . ?
N2A H2AB 0.8800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C3 H3D 0.9800 . ?
C5A C10A 1.428(6) . ?
C10A H10A 0.9500 . ?
C10A C9A 1.387(6) . ?
C4A H4AA 0.9800 . ?
C4A H4AB 0.9800 . ?
C4A H4AC 0.9800 . ?
C9A H9A 0.9500 . ?
C9A C8A 1.379(7) . ?
C8A H8A 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.522(7) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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
N3 Zn1 N1 75.44(10) . . ?
N3 Zn1 N1A 111.10(11) . . ?
N3 Zn1 O2 86.94(11) . . ?
N3A Zn1 N3 172.40(11) . . ?
N3A Zn1 N1 106.99(10) . . ?
N3A Zn1 N1A 76.28(10) . . ?
N3A Zn1 O2 90.53(11) . . ?
N1 Zn1 O2 162.37(10) . . ?
N1A Zn1 N1 90.29(10) . . ?
N1A Zn1 O2 95.90(12) . . ?
O7 S2 O8 113.94(15) . . ?
O7 S2 C14 102.99(16) . . ?
O6 S2 O7 116.57(15) . . ?
O6 S2 O8 114.10(15) . . ?
O6 S2 C14 103.50(16) . . ?
O8 S2 C14 103.43(17) . . ?
O4 S1 O3 115.27(15) . . ?
O4 S1 C13 104.18(16) . . ?
O3 S1 C13 102.75(17) . . ?
O5 S1 O4 116.06(17) . . ?
O5 S1 O3 114.30(17) . . ?
O5 S1 C13 101.56(18) . . ?
Zn1 N3 H3 119.3 . . ?
C2 N3 Zn1 121.5(2) . . ?
C2 N3 H3 119.3 . . ?
C2 O1 N1 111.7(2) . . ?
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
Zn1 N3A H3A 119.9 . . ?
C2A N3A Zn1 120.2(2) . . ?
C2A N3A H3A 119.9 . . ?
C2A N4A C3A 121.8(3) . . ?
C2A N4A C4A 118.6(3) . . ?
C4A N4A C3A 118.8(3) . . ?
O1 N1 Zn1 110.85(17) . . ?
C1 N1 Zn1 138.8(2) . . ?
C1 N1 O1 108.8(2) . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N4 C4 H4A 109.5 . . ?
N4 C4 H4B 109.5 . . ?
N4 C4 H4C 109.5 . . ?
C2 N4 C4 118.9(3) . . ?
C2 N4 C3 122.9(3) . . ?
C3 N4 C4 117.5(3) . . ?
O1A N1A Zn1 111.08(17) . . ?
C1A N1A Zn1 138.3(2) . . ?
C1A N1A O1A 108.2(3) . . ?
C2A O1A N1A 111.8(2) . . ?
N3 C2 O1 120.3(3) . . ?
N3 C2 N4 127.5(3) . . ?
N4 C2 O1 112.2(3) . . ?
N4A C3A H3AA 109.5 . . ?
N4A C3A H3AB 109.5 . . ?
N4A C3A H3AC 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
N3A C2A N4A 128.1(3) . . ?
N3A C2A O1A 120.0(3) . . ?
N4A C2A O1A 111.8(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 119.9(3) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C5 C6 Cl1 119.9(2) . . ?
C7 C6 Cl1 118.8(2) . . ?
C7 C6 C5 121.4(3) . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C5 121.0(3) . . ?
C5 C10 H10 119.5 . . ?
C6 C5 C1 123.4(3) . . ?
C10 C5 C6 118.0(3) . . ?
C10 C5 C1 118.6(3) . . ?
C7A C6A Cl1A 118.9(3) . . ?
C5A C6A Cl1A 119.9(3) . . ?
C5A C6A C7A 121.2(4) . . ?
N1A C1A N2A 126.1(3) . . ?
N1A C1A C5A 114.1(3) . . ?
N2A C1A C5A 119.7(3) . . ?
Zn1 O2 H2 114(2) . . ?
C11 O2 Zn1 133.8(3) . . ?
C11 O2 H2 109.6(19) . . ?
C6A C7A H7A 120.5 . . ?
C8A C7A C6A 119.0(4) . . ?
C8A C7A H7A 120.5 . . ?
N2 C1 C5 117.2(3) . . ?
N1 C1 N2 126.6(3) . . ?
N1 C1 C5 116.1(3) . . ?
F3 C13 S1 110.6(3) . . ?
F3 C13 F4 107.6(3) . . ?
F5 C13 S1 113.1(2) . . ?
F5 C13 F3 106.8(3) . . ?
F5 C13 F4 107.2(3) . . ?
F4 C13 S1 111.2(3) . . ?
F7 C14 S2 112.0(3) . . ?
F7 C14 F6 107.4(3) . . ?
F7 C14 F8 108.0(3) . . ?
F6 C14 S2 110.9(3) . . ?
F8 C14 S2 110.9(3) . . ?
F8 C14 F6 107.4(3) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 C8 119.7(3) . . ?
C6 C7 H7 120.1 . . ?
C1A N2A H2AA 120.0 . . ?
C1A N2A H2AB 120.0 . . ?
H2AA N2A H2AB 120.0 . . ?
N4 C3 H3B 109.5 . . ?
N4 C3 H3C 109.5 . . ?
N4 C3 H3D 109.5 . . ?
H3B C3 H3C 109.5 . . ?
H3B C3 H3D 109.5 . . ?
H3C C3 H3D 109.5 . . ?
C6A C5A C1A 123.0(4) . . ?
C6A C5A C10A 118.3(4) . . ?
C10A C5A C1A 118.6(3) . . ?
C5A C10A H10A 120.0 . . ?
C9A C10A C5A 119.9(4) . . ?
C9A C10A H10A 120.0 . . ?
N4A C4A H4AA 109.5 . . ?
N4A C4A H4AB 109.5 . . ?
N4A C4A H4AC 109.5 . . ?
H4AA C4A H4AB 109.5 . . ?
H4AA C4A H4AC 109.5 . . ?
H4AB C4A H4AC 109.5 . . ?
C10A C9A H9A 120.0 . . ?
C8A C9A C10A 119.9(5) . . ?
C8A C9A H9A 120.0 . . ?
C7A C8A C9A 121.6(4) . . ?
C7A C8A H8A 119.2 . . ?
C9A C8A H8A 119.2 . . ?
O2 C11 H11A 108.8 . . ?
O2 C11 H11B 108.8 . . ?
O2 C11 C12 113.7(4) . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_4c_OTf2
_database_code_depnum_ccdc_archive 'CCDC 1504002'
_audit_update_record             
;
2016-09-12 deposited with the CCDC.
2017-01-16 downloaded from the CCDC.
;
_audit_creation_date             2016-09-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H28 N8 O2 Zn, 2(C F3 O3 S)'
_chemical_formula_sum            'C14 H28 F6 N8 O8 S2 Zn'
_chemical_formula_weight         679.93
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Zn C20 S O3'
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   16.8415(3)
_cell_length_b                   20.4363(4)
_cell_length_c                   16.1946(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5573.83(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    18157
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.0990
_cell_measurement_theta_min      2.9460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.124
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2784
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            53585
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.649
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -41.00   43.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.4031   57.0000 -150.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega  -51.00   42.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.4031   38.0000   60.0000 93

#__ type_ start__ end____ width___ exp.time_
  3 omega   -8.00   18.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968  -99.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -12.00   67.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968  -99.0000  -90.0000 79

#__ type_ start__ end____ width___ exp.time_
  5 omega    2.00   93.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968   77.0000   90.0000 91

#__ type_ start__ end____ width___ exp.time_
  6 omega   36.00   68.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968  -99.0000   30.0000 32

#__ type_ start__ end____ width___ exp.time_
  7 omega   28.00   94.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968   57.0000  -90.0000 66

#__ type_ start__ end____ width___ exp.time_
  8 omega  -42.00  -11.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968  -57.0000 -120.0000 31
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0025460000
_diffrn_orient_matrix_UB_12      0.0339023000
_diffrn_orient_matrix_UB_13      0.0090199000
_diffrn_orient_matrix_UB_21      -0.0161837000
_diffrn_orient_matrix_UB_22      0.0074471000
_diffrn_orient_matrix_UB_23      -0.0393331000
_diffrn_orient_matrix_UB_31      -0.0387787000
_diffrn_orient_matrix_UB_32      -0.0008532000
_diffrn_orient_matrix_UB_33      0.0170333000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                11402
_reflns_number_total             12565
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_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 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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         1.272
_refine_diff_density_min         -1.113
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 
;
 Flack x determined using 4847 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     721
_refine_ls_number_reflns         12565
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.046
_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)+(0.0457P)²+7.9853P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1023
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C9-F12 \\sim C9-F10 \\sim C9-F11
 with sigma of 0.002
 S4-C10 \\sim S4-C9
 with sigma of 0.002
 C10-F8 \\sim C10-F7 \\sim C10-F9
 with sigma of 0.002
3. Uiso/Uaniso restraints and constraints
Uanis(C10) = Uanis(S4) = Uanis(F8) = Uanis(F7) = Uanis(F9) = Uanis(C9) =
Uanis(F10) = Uanis(F11) = Uanis(F12)
Uanis(C5C) = Uanis(C7C) = Uanis(C1C)
4. Rigid body (RIGU) restrains
 C8C, C7C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.008
 C6C, C5C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.008
5. Others
 Sof(F12)=Sof(C9)=Sof(F11)=Sof(F10)=Sof(O11)=1-FVAR(1)
 Sof(F9)=Sof(O10)=Sof(F8)=Sof(F7)=Sof(C10)=FVAR(1)
 Sof(C6C)=Sof(H6CA)=Sof(H6CB)=Sof(H6CC)=Sof(C5C)=Sof(H5CA)=Sof(H5CB)=1-FVAR(2)
 Sof(C7C)=Sof(H7CA)=Sof(H7CB)=Sof(C8C)=Sof(H8CA)=Sof(H8CB)=Sof(H8CC)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C5A(H5AA,H5AB), C5(H5A,H5B), C5B(H5BA,H5BB), C7C(H7CA,H7CB), C5C(H5CA,H5CB)
6.b Aromatic/amide H refined with riding coordinates:
 N3A(H3A), N3B(H3B), N3(H3), N3C(H3C)
6.c X=CH2 refined with riding coordinates:
 N2A(H2AA,H2AB), N2(H2A,H2B), N2C(H2CA,H2CB), N2B(H2BA,H2BB)
6.d Idealised Me refined as rotating group:
 C3C(H3CA,H3CB,H3CC), C4A(H4AA,H4AB,H4AC), C3B(H3BA,H3BB,H3BC), C4B(H4BA,H4BB,
 H4BC), C4(H4A,H4B,H4C), C4C(H4CA,H4CB,H4CC), C3A(H3AA,H3AB,H3AC), C6A(H6AA,
 H6AB,H6AC), C3(H3D,H3E,H3F), C6(H6A,H6B,H6C), C6B(H6BA,H6BB,H6BC), C8C(H8CA,
 H8CB,H8CC), C6C(H6CA,H6CB,H6CC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 0.77026(3) 0.94092(3) 0.69490(4) 0.01920(12) Uani 1 1 d . . . . .
Zn1B Zn 0.76138(3) 0.41954(3) 0.68561(4) 0.02366(14) Uani 1 1 d . . . . .
S1 S 0.66611(7) 1.02038(6) 0.86830(7) 0.0205(2) Uani 1 1 d . . . . .
S2 S 0.67706(7) 0.54063(6) 0.85327(7) 0.0191(2) Uani 1 1 d . . . . .
S3 S 0.60699(7) 0.81576(6) 0.72658(8) 0.0223(3) Uani 1 1 d . . . . .
S4 S 0.59322(9) 0.30390(7) 0.75486(11) 0.0350(3) Uani 1 1 d D . . . .
O3 O 0.7316(2) 0.98293(19) 0.8348(2) 0.0233(8) Uani 1 1 d . . . . .
O1A O 0.92835(19) 0.91962(16) 0.7687(2) 0.0174(7) Uani 1 1 d . . . . .
F6 F 0.7521(2) 0.59342(17) 0.9789(2) 0.0373(9) Uani 1 1 d . . . . .
O1B O 0.9156(2) 0.41471(16) 0.7704(2) 0.0194(7) Uani 1 1 d . . . . .
O1 O 0.7097(2) 0.95360(17) 0.5261(2) 0.0198(7) Uani 1 1 d . . . . .
F14 F 0.5492(2) 0.70195(17) 0.6801(2) 0.0417(9) Uani 1 1 d . . . . .
F4 F 0.6710(2) 0.65843(16) 0.9181(2) 0.0323(8) Uani 1 1 d . . . . .
O6 O 0.7431(2) 0.49813(17) 0.8341(2) 0.0200(7) Uani 1 1 d . . . . .
O13 O 0.6562(2) 0.78382(18) 0.7874(2) 0.0284(8) Uani 1 1 d . . . . .
N3A N 0.8113(2) 0.8633(2) 0.7530(2) 0.0179(8) Uani 1 1 d . . . . .
H3A H 0.7826 0.8288 0.7589 0.021 Uiso 1 1 calc R . . . .
O1C O 0.6910(2) 0.42873(16) 0.52190(19) 0.0185(7) Uani 1 1 d . . . . .
O2 O 0.6090(2) 1.04196(19) 0.8074(2) 0.0268(8) Uani 1 1 d . . . . .
O14 O 0.6459(2) 0.8667(2) 0.6803(3) 0.0393(10) Uani 1 1 d . . . . .
N3B N 0.8007(2) 0.3538(2) 0.7621(3) 0.0200(8) Uani 1 1 d . . . . .
H3B H 0.7727 0.3201 0.7747 0.024 Uiso 1 1 calc R . . . .
N1A N 0.8851(2) 0.97072(19) 0.7260(2) 0.0180(8) Uani 1 1 d . . . . .
N3 N 0.6945(2) 1.0043(2) 0.6513(2) 0.0181(8) Uani 1 1 d . . . . .
H3 H 0.6794 1.0378 0.6794 0.022 Uiso 1 1 calc R . . . .
N3C N 0.6908(2) 0.4869(2) 0.6429(2) 0.0183(8) Uani 1 1 d . . . . .
H3C H 0.6791 0.5211 0.6714 0.022 Uiso 1 1 calc R . . . .
O7 O 0.6226(2) 0.5159(2) 0.9140(3) 0.0333(9) Uani 1 1 d . . . . .
F5 F 0.7822(2) 0.63517(19) 0.8607(3) 0.0451(9) Uani 1 1 d . . . . .
N4C N 0.6048(2) 0.5111(2) 0.5319(2) 0.0202(8) Uani 1 1 d . . . . .
O5 O 0.6403(2) 0.5702(2) 0.7819(2) 0.0308(9) Uani 1 1 d . . . . .
N4A N 0.9203(3) 0.8199(2) 0.8257(3) 0.0217(9) Uani 1 1 d . . . . .
O4 O 0.6319(3) 0.9942(2) 0.9429(2) 0.0365(10) Uani 1 1 d . . . . .
N4B N 0.9068(3) 0.3242(2) 0.8487(3) 0.0213(9) Uani 1 1 d . . . . .
O12 O 0.5278(2) 0.8307(2) 0.7537(3) 0.0369(10) Uani 1 1 d . . . . .
N1B N 0.8769(2) 0.4531(2) 0.7064(3) 0.0231(9) Uani 1 1 d . . . . .
N1 N 0.7754(2) 0.9220(2) 0.5672(3) 0.0191(8) Uani 1 1 d . . . . .
F15 F 0.5528(3) 0.7734(3) 0.5843(2) 0.0627(14) Uani 1 1 d . . . . .
F3 F 0.7647(2) 1.0862(2) 0.9612(3) 0.0532(12) Uani 1 1 d . . . . .
N4 N 0.6019(2) 1.0160(2) 0.5416(3) 0.0205(8) Uani 1 1 d . . . . .
O9 O 0.6402(3) 0.28174(19) 0.8226(3) 0.0376(10) Uani 1 1 d . . . . .
F2 F 0.6591(2) 1.1388(2) 0.9287(3) 0.0562(13) Uani 1 1 d . . . . .
N2A N 1.0052(2) 1.0256(2) 0.7455(3) 0.0227(9) Uani 1 1 d . . . . .
H2AA H 1.0265 0.9924 0.7697 0.027 Uiso 1 1 calc R . . . .
H2AB H 1.0321 1.0609 0.7388 0.027 Uiso 1 1 calc R . . . .
O8 O 0.6201(2) 0.36410(18) 0.7176(3) 0.0309(9) Uani 1 1 d . . . . .
N1C N 0.7465(3) 0.3875(2) 0.5647(3) 0.0275(10) Uani 1 1 d . . . . .
N2 N 0.7896(3) 0.8771(2) 0.4355(3) 0.0254(10) Uani 1 1 d . . . . .
H2A H 0.7503 0.8991 0.4162 0.030 Uiso 1 1 calc R . . . .
H2B H 0.8156 0.8509 0.4040 0.030 Uiso 1 1 calc R . . . .
C2A C 0.8824(3) 0.8657(2) 0.7821(3) 0.0146(9) Uani 1 1 d . . . . .
C2C C 0.6624(3) 0.4777(2) 0.5702(3) 0.0145(9) Uani 1 1 d . . . . .
N2C N 0.7723(3) 0.3528(2) 0.4310(3) 0.0230(9) Uani 1 1 d . . . . .
H2CA H 0.7394 0.3804 0.4101 0.028 Uiso 1 1 calc R . . . .
H2CB H 0.7984 0.3268 0.3993 0.028 Uiso 1 1 calc R . . . .
C1A C 0.9305(3) 1.0221(2) 0.7186(3) 0.0169(9) Uani 1 1 d . . . . .
F13 F 0.6601(2) 0.7275(3) 0.6227(3) 0.0629(14) Uani 1 1 d . . . . .
C1 C 0.8104(3) 0.8838(2) 0.5143(3) 0.0175(9) Uani 1 1 d . . . . .
C8 C 0.7231(3) 0.6110(3) 0.9050(3) 0.0245(11) Uani 1 1 d . . . . .
N2B N 0.9724(3) 0.5298(2) 0.7470(3) 0.0295(10) Uani 1 1 d . . . . .
H2BA H 0.9921 0.5043 0.7840 0.035 Uiso 1 1 calc R . . . .
H2BB H 0.9920 0.5682 0.7397 0.035 Uiso 1 1 calc R . . . .
C2 C 0.6685(3) 0.9930(2) 0.5777(3) 0.0151(9) Uani 1 1 d . . . . .
C2B C 0.8714(3) 0.3627(2) 0.7937(3) 0.0163(9) Uani 1 1 d . . . . .
F9 F 0.6055(3) 0.1809(2) 0.7014(4) 0.0350(3) Uani 0.613(4) 1 d D . P A 1
C11 C 0.5919(3) 0.7511(3) 0.6494(3) 0.0332(13) Uani 1 1 d . . . . .
F1 F 0.7500(3) 1.1247(2) 0.8384(3) 0.0617(12) Uani 1 1 d . . . . .
C5A C 0.8949(3) 1.0808(3) 0.6774(3) 0.0248(11) Uani 1 1 d . . . . .
H5AA H 0.8998 1.1183 0.7136 0.030 Uiso 1 1 calc R . . . .
H5AB H 0.8387 1.0730 0.6681 0.030 Uiso 1 1 calc R . . . .
C7 C 0.7124(4) 1.0971(3) 0.9010(4) 0.0330(13) Uani 1 1 d . . . . .
C1B C 0.9115(3) 0.5097(2) 0.7011(3) 0.0240(10) Uani 1 1 d . . . . .
C1C C 0.7828(3) 0.3505(3) 0.5115(3) 0.0260(10) Uani 1 1 d . . . . .
C3C C 0.5794(3) 0.4965(3) 0.4481(3) 0.0290(12) Uani 1 1 d . . . . .
H3CA H 0.6139 0.5181 0.4096 0.044 Uiso 1 1 calc GR . . . .
H3CB H 0.5260 0.5116 0.4402 0.044 Uiso 1 1 calc GR . . . .
H3CC H 0.5815 0.4501 0.4391 0.044 Uiso 1 1 calc GR . . . .
C4A C 0.8809(3) 0.7575(2) 0.8430(4) 0.0255(11) Uani 1 1 d . . . . .
H4AA H 0.8475 0.7621 0.8906 0.038 Uiso 1 1 calc GR . . . .
H4AB H 0.9202 0.7244 0.8534 0.038 Uiso 1 1 calc GR . . . .
H4AC H 0.8492 0.7449 0.7963 0.038 Uiso 1 1 calc GR . . . .
C5 C 0.8770(3) 0.8426(3) 0.5469(3) 0.0220(10) Uani 1 1 d . . . . .
H5A H 0.8954 0.8607 0.5989 0.026 Uiso 1 1 calc R . . . .
H5B H 0.9210 0.8437 0.5083 0.026 Uiso 1 1 calc R . . . .
C3B C 0.9853(3) 0.3378(3) 0.8830(4) 0.0279(12) Uani 1 1 d . . . . .
H3BA H 1.0099 0.3725 0.8523 0.042 Uiso 1 1 calc GR . . . .
H3BB H 1.0176 0.2992 0.8794 0.042 Uiso 1 1 calc GR . . . .
H3BC H 0.9802 0.3506 0.9398 0.042 Uiso 1 1 calc GR . . . .
C4B C 0.8663(3) 0.2651(3) 0.8772(4) 0.0274(11) Uani 1 1 d . . . . .
H4BA H 0.8173 0.2768 0.9035 0.041 Uiso 1 1 calc GR . . . .
H4BB H 0.8996 0.2424 0.9159 0.041 Uiso 1 1 calc GR . . . .
H4BC H 0.8556 0.2371 0.8309 0.041 Uiso 1 1 calc GR . . . .
C4 C 0.5551(3) 1.0666(3) 0.5813(4) 0.0286(12) Uani 1 1 d . . . . .
H4A H 0.5604 1.0629 0.6401 0.043 Uiso 1 1 calc GR . . . .
H4B H 0.5004 1.0617 0.5661 0.043 Uiso 1 1 calc GR . . . .
H4C H 0.5738 1.1088 0.5638 0.043 Uiso 1 1 calc GR . . . .
C5B C 0.8785(4) 0.5548(3) 0.6349(4) 0.0380(15) Uani 1 1 d . . . . .
H5BA H 0.9219 0.5701 0.6006 0.046 Uiso 1 1 calc R . . . .
H5BB H 0.8427 0.5300 0.5999 0.046 Uiso 1 1 calc R . . . .
O10 O 0.5103(11) 0.2932(9) 0.7512(8) 0.048(4) Uani 0.613(4) 1 d . . P A 1
C4C C 0.5728(4) 0.5702(3) 0.5697(4) 0.0313(13) Uani 1 1 d . . . . .
H4CA H 0.5210 0.5612 0.5917 0.047 Uiso 1 1 calc GR . . . .
H4CB H 0.5690 0.6041 0.5289 0.047 Uiso 1 1 calc GR . . . .
H4CC H 0.6074 0.5842 0.6135 0.047 Uiso 1 1 calc GR . . . .
C3A C 0.9978(3) 0.8300(2) 0.8645(4) 0.0254(11) Uani 1 1 d . . . . .
H3AA H 1.0195 0.8711 0.8467 0.038 Uiso 1 1 calc GR . . . .
H3AB H 1.0330 0.7952 0.8489 0.038 Uiso 1 1 calc GR . . . .
H3AC H 0.9917 0.8303 0.9235 0.038 Uiso 1 1 calc GR . . . .
C6A C 0.9351(4) 1.0959(3) 0.5949(3) 0.0338(13) Uani 1 1 d . . . . .
H6AA H 0.9250 1.0610 0.5567 0.051 Uiso 1 1 calc GR . . . .
H6AB H 0.9913 1.1002 0.6032 0.051 Uiso 1 1 calc GR . . . .
H6AC H 0.9143 1.1361 0.5731 0.051 Uiso 1 1 calc GR . . . .
C3 C 0.5843(3) 1.0049(3) 0.4545(3) 0.0330(13) Uani 1 1 d . . . . .
H3D H 0.6030 1.0414 0.4226 0.049 Uiso 1 1 calc GR . . . .
H3E H 0.5280 1.0003 0.4472 0.049 Uiso 1 1 calc GR . . . .
H3F H 0.6104 0.9657 0.4363 0.049 Uiso 1 1 calc GR . . . .
F8 F 0.6018(4) 0.2507(3) 0.6002(3) 0.0350(3) Uani 0.613(4) 1 d D . P A 1
C6 C 0.8513(4) 0.7720(3) 0.5601(5) 0.0413(16) Uani 1 1 d . . . . .
H6A H 0.8355 0.7533 0.5083 0.062 Uiso 1 1 calc GR . . . .
H6B H 0.8074 0.7708 0.5979 0.062 Uiso 1 1 calc GR . . . .
H6C H 0.8948 0.7474 0.5825 0.062 Uiso 1 1 calc GR . . . .
C7C C 0.8515(11) 0.3093(8) 0.5424(9) 0.0260(10) Uani 0.46(2) 1 d . U P B 1
H7CA H 0.8657 0.3246 0.5971 0.031 Uiso 0.46(2) 1 calc R . P B 1
H7CB H 0.8332 0.2646 0.5479 0.031 Uiso 0.46(2) 1 calc R . P B 1
F7 F 0.7061(3) 0.2403(3) 0.6688(4) 0.0350(3) Uani 0.613(4) 1 d D . P A 1
C6B C 0.8354(4) 0.6122(3) 0.6687(4) 0.0454(16) Uani 1 1 d . . . . .
H6BA H 0.8148 0.6380 0.6240 0.068 Uiso 1 1 calc GR . . . .
H6BB H 0.8712 0.6383 0.7010 0.068 Uiso 1 1 calc GR . . . .
H6BC H 0.7924 0.5975 0.7028 0.068 Uiso 1 1 calc GR . . . .
C10 C 0.6260(3) 0.2429(3) 0.6795(4) 0.0350(3) Uani 0.613(4) 1 d D . P A 1
C8C C 0.9259(10) 0.3090(11) 0.4898(10) 0.035(4) Uani 0.46(2) 1 d . U P B 1
H8CA H 0.9145 0.2890 0.4375 0.052 Uiso 0.46(2) 1 calc GR . P B 1
H8CB H 0.9668 0.2847 0.5175 0.052 Uiso 0.46(2) 1 calc GR . P B 1
H8CC H 0.9435 0.3532 0.4812 0.052 Uiso 0.46(2) 1 calc GR . P B 1
F12 F 0.5609(5) 0.1902(4) 0.7055(6) 0.0350(3) Uani 0.387(4) 1 d D . P A 2
C9 C 0.5921(5) 0.2413(4) 0.6743(4) 0.0350(3) Uani 0.387(4) 1 d D . P A 2
F11 F 0.5616(6) 0.2666(4) 0.6098(6) 0.0350(3) Uani 0.387(4) 1 d D . P A 2
F10 F 0.6651(6) 0.2329(4) 0.6568(6) 0.0350(3) Uani 0.387(4) 1 d D . P A 2
O11 O 0.5095(17) 0.3075(14) 0.7860(15) 0.055(7) Uani 0.387(4) 1 d . . P A 2
C6C C 0.9135(10) 0.3004(10) 0.532(2) 0.075(8) Uani 0.54(2) 1 d . U P B 2
H6CA H 0.9203 0.3107 0.4742 0.112 Uiso 0.54(2) 1 calc GR . P B 2
H6CB H 0.9403 0.2601 0.5440 0.112 Uiso 0.54(2) 1 calc GR . P B 2
H6CC H 0.9353 0.3349 0.5647 0.112 Uiso 0.54(2) 1 calc GR . P B 2
C5C C 0.8272(9) 0.2932(7) 0.5500(8) 0.0260(10) Uani 0.54(2) 1 d . U P B 2
H5CA H 0.8188 0.2928 0.6093 0.031 Uiso 0.54(2) 1 calc R . P B 2
H5CB H 0.8076 0.2523 0.5275 0.031 Uiso 0.54(2) 1 calc R . P B 2


_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 N3A 1.970(4) . ?
Zn1 N1A 2.089(4) . ?
Zn1 N3 1.950(4) . ?
Zn1 N1 2.105(4) . ?
Zn1B N3B 1.944(4) . ?
Zn1B N3C 1.945(4) . ?
Zn1B N1B 2.090(4) . ?
Zn1B N1C 2.079(4) . ?
S1 O3 1.448(4) . ?
S1 O2 1.448(4) . ?
S1 O4 1.441(4) . ?
S1 C7 1.829(6) . ?
S2 O6 1.445(4) . ?
S2 O7 1.437(4) . ?
S2 O5 1.444(4) . ?
S2 C8 1.837(5) . ?
S3 O13 1.444(4) . ?
S3 O14 1.441(4) . ?
S3 O12 1.437(4) . ?
S3 C11 1.837(6) . ?
S4 O9 1.426(4) . ?
S4 O8 1.443(4) . ?
S4 O10 1.415(19) . ?
S4 C10 1.829(8) . ?
S4 C9 1.827(8) . ?
S4 O11 1.50(3) . ?
O1A N1A 1.449(5) . ?
O1A C2A 1.363(5) . ?
F6 C8 1.341(6) . ?
O1B N1B 1.453(5) . ?
O1B C2B 1.351(6) . ?
O1 N1 1.444(5) . ?
O1 C2 1.352(6) . ?
F14 C11 1.332(7) . ?
F4 C8 1.325(6) . ?
N3A H3A 0.8600 . ?
N3A C2A 1.288(6) . ?
O1C N1C 1.438(5) . ?
O1C C2C 1.358(5) . ?
N3B H3B 0.8600 . ?
N3B C2B 1.308(6) . ?
N1A C1A 1.305(6) . ?
N3 H3 0.8600 . ?
N3 C2 1.291(6) . ?
N3C H3C 0.8600 . ?
N3C C2C 1.285(6) . ?
F5 C8 1.322(7) . ?
N4C C2C 1.338(6) . ?
N4C C3C 1.454(6) . ?
N4C C4C 1.458(7) . ?
N4A C2A 1.336(6) . ?
N4A C4A 1.465(6) . ?
N4A C3A 1.464(6) . ?
N4B C2B 1.330(6) . ?
N4B C3B 1.461(7) . ?
N4B C4B 1.462(6) . ?
N1B C1B 1.299(7) . ?
N1 C1 1.301(6) . ?
F15 C11 1.325(7) . ?
F3 C7 1.331(7) . ?
N4 C2 1.349(6) . ?
N4 C4 1.451(7) . ?
N4 C3 1.460(7) . ?
F2 C7 1.318(7) . ?
N2A H2AA 0.8600 . ?
N2A H2AB 0.8600 . ?
N2A C1A 1.333(6) . ?
N1C C1C 1.300(7) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C1 1.329(6) . ?
N2C H2CA 0.8600 . ?
N2C H2CB 0.8600 . ?
N2C C1C 1.317(7) . ?
C1A C5A 1.497(7) . ?
F13 C11 1.318(7) . ?
C1 C5 1.499(7) . ?
N2B H2BA 0.8600 . ?
N2B H2BB 0.8600 . ?
N2B C1B 1.331(7) . ?
F9 C10 1.359(5) . ?
F1 C7 1.322(8) . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C5A C6A 1.530(8) . ?
C1B C5B 1.519(7) . ?
C1C C7C 1.515(15) . ?
C1C C5C 1.522(12) . ?
C3C H3CA 0.9600 . ?
C3C H3CB 0.9600 . ?
C3C H3CC 0.9600 . ?
C4A H4AA 0.9600 . ?
C4A H4AB 0.9600 . ?
C4A H4AC 0.9600 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.520(8) . ?
C3B H3BA 0.9600 . ?
C3B H3BB 0.9600 . ?
C3B H3BC 0.9600 . ?
C4B H4BA 0.9600 . ?
C4B H4BB 0.9600 . ?
C4B H4BC 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5B H5BA 0.9700 . ?
C5B H5BB 0.9700 . ?
C5B C6B 1.484(9) . ?
C4C H4CA 0.9600 . ?
C4C H4CB 0.9600 . ?
C4C H4CC 0.9600 . ?
C3A H3AA 0.9600 . ?
C3A H3AB 0.9600 . ?
C3A H3AC 0.9600 . ?
C6A H6AA 0.9600 . ?
C6A H6AB 0.9600 . ?
C6A H6AC 0.9600 . ?
C3 H3D 0.9600 . ?
C3 H3E 0.9600 . ?
C3 H3F 0.9600 . ?
F8 C10 1.357(5) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7C H7CA 0.9700 . ?
C7C H7CB 0.9700 . ?
C7C C8C 1.51(2) . ?
F7 C10 1.361(5) . ?
C6B H6BA 0.9600 . ?
C6B H6BB 0.9600 . ?
C6B H6BC 0.9600 . ?
C8C H8CA 0.9600 . ?
C8C H8CB 0.9600 . ?
C8C H8CC 0.9600 . ?
F12 C9 1.274(6) . ?
C9 F11 1.274(6) . ?
C9 F10 1.274(6) . ?
C6C H6CA 0.9600 . ?
C6C H6CB 0.9600 . ?
C6C H6CC 0.9600 . ?
C6C C5C 1.49(2) . ?
C5C H5CA 0.9700 . ?
C5C H5CB 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3A Zn1 N1A 78.15(16) . . ?
N3A Zn1 N1 107.86(16) . . ?
N1A Zn1 N1 104.61(16) . . ?
N3 Zn1 N3A 159.62(17) . . ?
N3 Zn1 N1A 119.93(16) . . ?
N3 Zn1 N1 78.11(16) . . ?
N3B Zn1B N3C 157.46(17) . . ?
N3B Zn1B N1B 78.84(17) . . ?
N3B Zn1B N1C 115.03(18) . . ?
N3C Zn1B N1B 113.23(17) . . ?
N3C Zn1B N1C 79.33(17) . . ?
N1C Zn1B N1B 111.52(18) . . ?
O3 S1 C7 103.7(3) . . ?
O2 S1 O3 114.3(2) . . ?
O2 S1 C7 102.7(3) . . ?
O4 S1 O3 115.0(2) . . ?
O4 S1 O2 114.7(3) . . ?
O4 S1 C7 104.2(3) . . ?
O6 S2 C8 104.1(2) . . ?
O7 S2 O6 115.3(2) . . ?
O7 S2 O5 114.9(3) . . ?
O7 S2 C8 103.5(2) . . ?
O5 S2 O6 114.2(2) . . ?
O5 S2 C8 102.6(2) . . ?
O13 S3 C11 102.6(3) . . ?
O14 S3 O13 114.9(2) . . ?
O14 S3 C11 103.3(3) . . ?
O12 S3 O13 114.9(3) . . ?
O12 S3 O14 115.3(3) . . ?
O12 S3 C11 103.4(2) . . ?
O9 S4 O8 114.7(2) . . ?
O9 S4 C10 97.4(3) . . ?
O9 S4 C9 109.4(3) . . ?
O9 S4 O11 106.2(11) . . ?
O8 S4 C10 102.0(2) . . ?
O8 S4 C9 107.5(3) . . ?
O8 S4 O11 113.1(11) . . ?
O10 S4 O9 122.1(7) . . ?
O10 S4 O8 115.0(8) . . ?
O10 S4 C10 99.5(6) . . ?
O11 S4 C9 105.4(10) . . ?
C2A O1A N1A 111.9(3) . . ?
C2B O1B N1B 112.2(3) . . ?
C2 O1 N1 112.0(3) . . ?
Zn1 N3A H3A 121.0 . . ?
C2A N3A Zn1 118.0(3) . . ?
C2A N3A H3A 121.0 . . ?
C2C O1C N1C 112.6(3) . . ?
Zn1B N3B H3B 121.2 . . ?
C2B N3B Zn1B 117.6(3) . . ?
C2B N3B H3B 121.2 . . ?
O1A N1A Zn1 111.7(3) . . ?
C1A N1A Zn1 139.0(3) . . ?
C1A N1A O1A 109.2(4) . . ?
Zn1 N3 H3 122.0 . . ?
C2 N3 Zn1 115.9(3) . . ?
C2 N3 H3 122.0 . . ?
Zn1B N3C H3C 121.6 . . ?
C2C N3C Zn1B 116.7(3) . . ?
C2C N3C H3C 121.6 . . ?
C2C N4C C3C 122.8(4) . . ?
C2C N4C C4C 119.7(4) . . ?
C3C N4C C4C 117.0(4) . . ?
C2A N4A C4A 119.8(4) . . ?
C2A N4A C3A 123.6(4) . . ?
C3A N4A C4A 116.4(4) . . ?
C2B N4B C3B 123.2(4) . . ?
C2B N4B C4B 119.5(4) . . ?
C3B N4B C4B 117.3(4) . . ?
O1B N1B Zn1B 110.8(3) . . ?
C1B N1B Zn1B 134.4(3) . . ?
C1B N1B O1B 109.1(4) . . ?
O1 N1 Zn1 109.8(3) . . ?
C1 N1 Zn1 140.9(3) . . ?
C1 N1 O1 108.2(4) . . ?
C2 N4 C4 120.5(4) . . ?
C2 N4 C3 122.2(4) . . ?
C4 N4 C3 115.4(4) . . ?
H2AA N2A H2AB 120.0 . . ?
C1A N2A H2AA 120.0 . . ?
C1A N2A H2AB 120.0 . . ?
O1C N1C Zn1B 110.3(3) . . ?
C1C N1C Zn1B 138.7(4) . . ?
C1C N1C O1C 109.1(4) . . ?
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
N3A C2A O1A 120.1(4) . . ?
N3A C2A N4A 127.6(4) . . ?
N4A C2A O1A 112.4(4) . . ?
N3C C2C O1C 120.3(4) . . ?
N3C C2C N4C 128.4(4) . . ?
N4C C2C O1C 111.4(4) . . ?
H2CA N2C H2CB 120.0 . . ?
C1C N2C H2CA 120.0 . . ?
C1C N2C H2CB 120.0 . . ?
N1A C1A N2A 124.4(4) . . ?
N1A C1A C5A 116.7(4) . . ?
N2A C1A C5A 118.8(4) . . ?
N1 C1 N2 125.0(5) . . ?
N1 C1 C5 116.3(4) . . ?
N2 C1 C5 118.6(4) . . ?
F6 C8 S2 110.5(4) . . ?
F4 C8 S2 111.4(4) . . ?
F4 C8 F6 107.2(4) . . ?
F5 C8 S2 111.3(4) . . ?
F5 C8 F6 108.1(5) . . ?
F5 C8 F4 108.2(5) . . ?
H2BA N2B H2BB 120.0 . . ?
C1B N2B H2BA 120.0 . . ?
C1B N2B H2BB 120.0 . . ?
N3 C2 O1 120.2(4) . . ?
N3 C2 N4 128.3(4) . . ?
N4 C2 O1 111.5(4) . . ?
N3B C2B O1B 120.0(4) . . ?
N3B C2B N4B 126.0(5) . . ?
N4B C2B O1B 114.0(4) . . ?
F14 C11 S3 111.3(4) . . ?
F15 C11 S3 111.2(5) . . ?
F15 C11 F14 106.7(5) . . ?
F13 C11 S3 111.4(4) . . ?
F13 C11 F14 108.5(6) . . ?
F13 C11 F15 107.4(5) . . ?
C1A C5A H5AA 109.2 . . ?
C1A C5A H5AB 109.2 . . ?
C1A C5A C6A 111.9(4) . . ?
H5AA C5A H5AB 107.9 . . ?
C6A C5A H5AA 109.2 . . ?
C6A C5A H5AB 109.2 . . ?
F3 C7 S1 110.6(4) . . ?
F2 C7 S1 111.3(4) . . ?
F2 C7 F3 108.0(5) . . ?
F2 C7 F1 108.1(6) . . ?
F1 C7 S1 110.4(4) . . ?
F1 C7 F3 108.5(5) . . ?
N1B C1B N2B 125.7(5) . . ?
N1B C1B C5B 115.0(5) . . ?
N2B C1B C5B 119.3(5) . . ?
N1C C1C N2C 124.9(5) . . ?
N1C C1C C7C 117.6(7) . . ?
N1C C1C C5C 114.0(6) . . ?
N2C C1C C7C 116.7(7) . . ?
N2C C1C C5C 120.0(6) . . ?
N4C C3C H3CA 109.5 . . ?
N4C C3C H3CB 109.5 . . ?
N4C C3C H3CC 109.5 . . ?
H3CA C3C H3CB 109.5 . . ?
H3CA C3C H3CC 109.5 . . ?
H3CB C3C H3CC 109.5 . . ?
N4A C4A H4AA 109.5 . . ?
N4A C4A H4AB 109.5 . . ?
N4A C4A H4AC 109.5 . . ?
H4AA C4A H4AB 109.5 . . ?
H4AA C4A H4AC 109.5 . . ?
H4AB C4A H4AC 109.5 . . ?
C1 C5 H5A 109.3 . . ?
C1 C5 H5B 109.3 . . ?
C1 C5 C6 111.7(4) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
N4B C3B H3BA 109.5 . . ?
N4B C3B H3BB 109.5 . . ?
N4B C3B H3BC 109.5 . . ?
H3BA C3B H3BB 109.5 . . ?
H3BA C3B H3BC 109.5 . . ?
H3BB C3B H3BC 109.5 . . ?
N4B C4B H4BA 109.5 . . ?
N4B C4B H4BB 109.5 . . ?
N4B C4B H4BC 109.5 . . ?
H4BA C4B H4BB 109.5 . . ?
H4BA C4B H4BC 109.5 . . ?
H4BB C4B H4BC 109.5 . . ?
N4 C4 H4A 109.5 . . ?
N4 C4 H4B 109.5 . . ?
N4 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1B C5B H5BA 108.9 . . ?
C1B C5B H5BB 108.9 . . ?
H5BA C5B H5BB 107.7 . . ?
C6B C5B C1B 113.4(6) . . ?
C6B C5B H5BA 108.9 . . ?
C6B C5B H5BB 108.9 . . ?
N4C C4C H4CA 109.5 . . ?
N4C C4C H4CB 109.5 . . ?
N4C C4C H4CC 109.5 . . ?
H4CA C4C H4CB 109.5 . . ?
H4CA C4C H4CC 109.5 . . ?
H4CB C4C H4CC 109.5 . . ?
N4A C3A H3AA 109.5 . . ?
N4A C3A H3AB 109.5 . . ?
N4A C3A H3AC 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
C5A C6A H6AA 109.5 . . ?
C5A C6A H6AB 109.5 . . ?
C5A C6A H6AC 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
N4 C3 H3D 109.5 . . ?
N4 C3 H3E 109.5 . . ?
N4 C3 H3F 109.5 . . ?
H3D C3 H3E 109.5 . . ?
H3D C3 H3F 109.5 . . ?
H3E C3 H3F 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1C C7C H7CA 108.1 . . ?
C1C C7C H7CB 108.1 . . ?
H7CA C7C H7CB 107.3 . . ?
C8C C7C C1C 116.6(12) . . ?
C8C C7C H7CA 108.1 . . ?
C8C C7C H7CB 108.1 . . ?
C5B C6B H6BA 109.5 . . ?
C5B C6B H6BB 109.5 . . ?
C5B C6B H6BC 109.5 . . ?
H6BA C6B H6BB 109.5 . . ?
H6BA C6B H6BC 109.5 . . ?
H6BB C6B H6BC 109.5 . . ?
F9 C10 S4 112.6(5) . . ?
F9 C10 F7 104.4(5) . . ?
F8 C10 S4 117.5(5) . . ?
F8 C10 F9 106.3(6) . . ?
F8 C10 F7 100.4(6) . . ?
F7 C10 S4 114.2(4) . . ?
C7C C8C H8CA 109.5 . . ?
C7C C8C H8CB 109.5 . . ?
C7C C8C H8CC 109.5 . . ?
H8CA C8C H8CB 109.5 . . ?
H8CA C8C H8CC 109.5 . . ?
H8CB C8C H8CC 109.5 . . ?
F12 C9 S4 107.2(6) . . ?
F11 C9 S4 107.8(6) . . ?
F11 C9 F12 119.4(8) . . ?
F11 C9 F10 105.1(8) . . ?
F10 C9 S4 104.1(6) . . ?
F10 C9 F12 112.0(8) . . ?
H6CA C6C H6CB 109.5 . . ?
H6CA C6C H6CC 109.5 . . ?
H6CB C6C H6CC 109.5 . . ?
C5C C6C H6CA 109.5 . . ?
C5C C6C H6CB 109.5 . . ?
C5C C6C H6CC 109.5 . . ?
C1C C5C H5CA 109.9 . . ?
C1C C5C H5CB 109.9 . . ?
C6C C5C C1C 108.8(12) . . ?
C6C C5C H5CA 109.9 . . ?
C6C C5C H5CB 109.9 . . ?
H5CA C5C H5CB 108.3 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_5d_OTf
_database_code_depnum_ccdc_archive 'CCDC 1504003'
_audit_update_record             
;
2016-09-12 deposited with the CCDC.
2017-01-16 downloaded from the CCDC.
;
_audit_creation_date             2016-09-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C F3 O3 S, C8 H19 N4 O'
_chemical_formula_sum            'C9 H19 F3 N4 O4 S'
_chemical_formula_weight         336.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'zn1 s2 f6 c16 H22 O6 n8'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.8893(13)
_cell_length_b                   18.4419(14)
_cell_length_c                   7.2746(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.177(11)
_cell_angle_gamma                90
_cell_volume                     1553.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1856
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.0670
_cell_measurement_theta_min      3.1890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7523
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.824
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -96.00  -40.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.5643 -178.0000  -60.0000 56

#__ type_ start__ end____ width___ exp.time_
  2 omega  -88.00    1.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.5643  -57.0000  120.0000 89

#__ type_ start__ end____ width___ exp.time_
  3 omega  -89.00  -45.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.5643 -178.0000 -150.0000 44

#__ type_ start__ end____ width___ exp.time_
  4 omega   12.00   58.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       21.5018  -19.0000  120.0000 46

#__ type_ start__ end____ width___ exp.time_
  5 omega  -24.00    1.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.5643  -99.0000  -90.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0434001000
_diffrn_orient_matrix_UB_12      -0.0251394000
_diffrn_orient_matrix_UB_13      -0.0101683000
_diffrn_orient_matrix_UB_21      -0.0402615000
_diffrn_orient_matrix_UB_22      -0.0178745000
_diffrn_orient_matrix_UB_23      -0.0726744000
_diffrn_orient_matrix_UB_31      0.0160003000
_diffrn_orient_matrix_UB_32      0.0229035000
_diffrn_orient_matrix_UB_33      -0.0681494000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2644
_reflns_number_total             3561
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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         0.458
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3561
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.055
_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)+(0.0539P)²+0.2474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1229
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a X=CH2 refined with riding coordinates:
 N3(H3A,H3B), N2(H2A,H2B)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C3(H3C,H3D,H3E), C7(H7A,H7B,H7C), C6(H6A,H6B,H6C), C8(H8A,
 H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
S1 S 0.18557(5) 0.56824(3) 0.47581(8) 0.02410(16) Uani 1 1 d . . . . .
F1 F 0.40664(11) 0.59817(8) 0.54956(19) 0.0346(3) Uani 1 1 d . . . . .
O2 O 0.20463(15) 0.51472(9) 0.3416(2) 0.0370(4) Uani 1 1 d . . . . .
F3 F 0.29886(12) 0.68557(8) 0.6057(2) 0.0398(4) Uani 1 1 d . . . . .
F2 F 0.30434(12) 0.65956(9) 0.3194(2) 0.0429(4) Uani 1 1 d . . . . .
O4 O 0.08490(14) 0.61295(9) 0.4119(3) 0.0367(4) Uani 1 1 d . . . . .
O1 O 0.11762(12) 0.25575(8) 0.7551(2) 0.0235(3) Uani 1 1 d . . . . .
O3 O 0.20339(15) 0.54282(9) 0.6673(2) 0.0359(4) Uani 1 1 d . . . . .
N4 N 0.00764(15) 0.16078(9) 0.6316(3) 0.0217(4) Uani 1 1 d . . . . .
N1 N 0.23798(16) 0.27415(10) 0.8520(3) 0.0247(4) Uani 1 1 d . . . . .
N3 N 0.18936(16) 0.14112(10) 0.8214(3) 0.0251(4) Uani 1 1 d . . . . .
H3A H 0.1815 0.0938 0.8094 0.030 Uiso 1 1 calc R . . . .
H3B H 0.2534 0.1596 0.8903 0.030 Uiso 1 1 calc R . . . .
N2 N 0.16728(16) 0.39100(10) 0.7666(3) 0.0255(4) Uani 1 1 d . . . . .
H2A H 0.0966 0.3755 0.7190 0.031 Uiso 1 1 calc R . . . .
H2B H 0.1831 0.4376 0.7649 0.031 Uiso 1 1 calc R . . . .
C9 C 0.30530(19) 0.63108(13) 0.4879(3) 0.0260(5) Uani 1 1 d . . . . .
C2 C 0.10529(18) 0.18419(11) 0.7362(3) 0.0199(4) Uani 1 1 d . . . . .
C1 C 0.25064(18) 0.34373(11) 0.8414(3) 0.0200(4) Uani 1 1 d . . . . .
C5 C 0.37364(18) 0.37193(12) 0.9149(3) 0.0224(5) Uani 1 1 d . . . . .
C4 C -0.0109(2) 0.08289(11) 0.5992(3) 0.0248(5) Uani 1 1 d . . . . .
H4A H -0.0144 0.0591 0.7182 0.037 Uiso 1 1 calc GR . . . .
H4B H 0.0531 0.0625 0.5516 0.037 Uiso 1 1 calc GR . . . .
H4C H -0.0836 0.0750 0.5063 0.037 Uiso 1 1 calc GR . . . .
C3 C -0.0876(2) 0.20884(13) 0.5450(4) 0.0328(6) Uani 1 1 d . . . . .
H3C H -0.0655 0.2593 0.5771 0.049 Uiso 1 1 calc GR . . . .
H3D H -0.1561 0.1966 0.5922 0.049 Uiso 1 1 calc GR . . . .
H3E H -0.1050 0.2028 0.4075 0.049 Uiso 1 1 calc GR . . . .
C7 C 0.4203(2) 0.39345(13) 0.7415(3) 0.0273(5) Uani 1 1 d . . . . .
H7A H 0.3711 0.4312 0.6701 0.041 Uiso 1 1 calc GR . . . .
H7B H 0.4203 0.3509 0.6608 0.041 Uiso 1 1 calc GR . . . .
H7C H 0.4994 0.4119 0.7834 0.041 Uiso 1 1 calc GR . . . .
C6 C 0.3737(2) 0.43840(12) 1.0415(3) 0.0277(5) Uani 1 1 d . . . . .
H6A H 0.3388 0.4255 1.1468 0.042 Uiso 1 1 calc GR . . . .
H6B H 0.3291 0.4775 0.9677 0.042 Uiso 1 1 calc GR . . . .
H6C H 0.4534 0.4547 1.0909 0.042 Uiso 1 1 calc GR . . . .
C8 C 0.4521(2) 0.31358(13) 1.0263(3) 0.0320(6) Uani 1 1 d . . . . .
H8A H 0.4552 0.2718 0.9443 0.048 Uiso 1 1 calc GR . . . .
H8B H 0.4213 0.2982 1.1342 0.048 Uiso 1 1 calc GR . . . .
H8C H 0.5300 0.3333 1.0719 0.048 Uiso 1 1 calc GR . . . .


_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
S1 O2 1.4419(17) . ?
S1 O4 1.4405(17) . ?
S1 O3 1.4387(17) . ?
S1 C9 1.822(2) . ?
F1 C9 1.332(2) . ?
F3 C9 1.334(3) . ?
F2 C9 1.331(3) . ?
O1 N1 1.483(2) . ?
O1 C2 1.331(3) . ?
N4 C2 1.308(3) . ?
N4 C4 1.464(3) . ?
N4 C3 1.463(3) . ?
N1 C1 1.296(3) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N3 C2 1.316(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C1 1.339(3) . ?
C1 C5 1.529(3) . ?
C5 C7 1.542(3) . ?
C5 C6 1.533(3) . ?
C5 C8 1.530(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C3 H3C 0.9800 . ?
C3 H3D 0.9800 . ?
C3 H3E 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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 S1 C9 103.09(10) . . ?
O4 S1 O2 114.86(11) . . ?
O4 S1 C9 103.53(10) . . ?
O3 S1 O2 114.91(11) . . ?
O3 S1 O4 115.29(11) . . ?
O3 S1 C9 102.68(11) . . ?
C2 O1 N1 110.33(16) . . ?
C2 N4 C4 119.88(18) . . ?
C2 N4 C3 123.23(18) . . ?
C3 N4 C4 116.88(17) . . ?
C1 N1 O1 108.10(17) . . ?
H3A N3 H3B 120.0 . . ?
C2 N3 H3A 120.0 . . ?
C2 N3 H3B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
F1 C9 S1 111.29(16) . . ?
F1 C9 F3 107.86(18) . . ?
F3 C9 S1 110.57(15) . . ?
F2 C9 S1 111.34(16) . . ?
F2 C9 F1 107.88(17) . . ?
F2 C9 F3 107.75(19) . . ?
N4 C2 O1 116.70(19) . . ?
N4 C2 N3 123.6(2) . . ?
N3 C2 O1 119.72(19) . . ?
N1 C1 N2 125.7(2) . . ?
N1 C1 C5 115.51(19) . . ?
N2 C1 C5 118.75(18) . . ?
C1 C5 C7 107.19(17) . . ?
C1 C5 C6 110.59(17) . . ?
C6 C5 C7 109.55(18) . . ?
C8 C5 C1 111.41(18) . . ?
C8 C5 C7 108.94(18) . . ?
C8 C5 C6 109.11(18) . . ?
N4 C4 H4A 109.5 . . ?
N4 C4 H4B 109.5 . . ?
N4 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N4 C3 H3C 109.5 . . ?
N4 C3 H3D 109.5 . . ?
N4 C3 H3E 109.5 . . ?
H3C C3 H3D 109.5 . . ?
H3C C3 H3E 109.5 . . ?
H3D C3 H3E 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_5a_OTf
_database_code_depnum_ccdc_archive 'CCDC 1504004'
_audit_update_record             
;
2016-10-12 deposited with the CCDC.
2017-01-16 downloaded from the CCDC.
;
_audit_creation_date             2016-10-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C F3 O3 S, C10 H15 N4 O'
_chemical_formula_sum            'C11 H15 F3 N4 O4 S'
_chemical_formula_weight         356.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Zn C22 H28 N8 O8 F6 S2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   16.7859(5)
_cell_length_b                   8.3599(2)
_cell_length_c                   21.9907(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.745(2)
_cell_angle_gamma                90
_cell_volume                     3085.67(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8632
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.5690
_cell_measurement_theta_min      4.0250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.429
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1226
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21892
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.503
_diffrn_reflns_theta_min         4.021
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -93.00  -41.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -38.0000  150.0000 52

#__ type_ start__ end____ width___ exp.time_
  2 omega  -50.00   32.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000    0.0000 82

#__ type_ start__ end____ width___ exp.time_
  3 omega  -40.00   25.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -90.0000 65

#__ type_ start__ end____ width___ exp.time_
  4 omega  -86.00   41.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   19.0000 -150.0000 127

#__ type_ start__ end____ width___ exp.time_
  5 omega   23.00   78.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000   60.0000 55

#__ type_ start__ end____ width___ exp.time_
  6 omega   71.00  127.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787 -178.0000  -60.0000 56

#__ type_ start__ end____ width___ exp.time_
  7 omega   20.00   59.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000  -30.0000 39

#__ type_ start__ end____ width___ exp.time_
  8 omega   40.00   66.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -64.0000   61.8738 26

#__ type_ start__ end____ width___ exp.time_
  9 omega  110.00  177.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -10.0000    3.4901 67

#__ type_ start__ end____ width___ exp.time_
 10 omega   45.00  119.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -122.0000   69.4356 74

#__ type_ start__ end____ width___ exp.time_
 11 omega   90.00  117.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -79.0000  -38.8604 27

#__ type_ start__ end____ width___ exp.time_
 12 omega   31.00   56.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega   45.00   98.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
 14 omega   35.00   78.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -90.0000 43

#__ type_ start__ end____ width___ exp.time_
 15 omega   50.00   76.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -79.0000  -38.8604 26

#__ type_ start__ end____ width___ exp.time_
 16 omega  114.00  141.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -10.0000  147.9364 27

#__ type_ start__ end____ width___ exp.time_
 17 omega   28.00   86.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -10.0000    3.4901 58

#__ type_ start__ end____ width___ exp.time_
 18 omega   59.00   94.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000    0.0000 35

#__ type_ start__ end____ width___ exp.time_
 19 omega   36.00   62.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   48.00   74.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega  107.00  146.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  150.0000 39

#__ type_ start__ end____ width___ exp.time_
 22 omega   73.00  107.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 34

#__ type_ start__ end____ width___ exp.time_
 23 omega   79.00  115.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   90.0000 36

#__ type_ start__ end____ width___ exp.time_
 24 omega  108.00  144.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   60.0000 36

#__ type_ start__ end____ width___ exp.time_
 25 omega   48.00   89.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 41

#__ type_ start__ end____ width___ exp.time_
 26 omega   63.00  105.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  150.0000 42

#__ type_ start__ end____ width___ exp.time_
 27 omega   99.00  125.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 28 omega   89.00  128.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -120.0000 39

#__ type_ start__ end____ width___ exp.time_
 29 omega   39.00   89.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 50

#__ type_ start__ end____ width___ exp.time_
 30 omega   93.00  126.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  150.0000 33

#__ type_ start__ end____ width___ exp.time_
 31 omega   74.00  110.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -113.0000  143.0000 36

#__ type_ start__ end____ width___ exp.time_
 32 omega   65.00  100.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -10.0000  147.9364 35

#__ type_ start__ end____ width___ exp.time_
 33 omega   45.00   93.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 48

#__ type_ start__ end____ width___ exp.time_
 34 omega  122.00  147.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 35 omega  109.00  175.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000    0.0000 66

#__ type_ start__ end____ width___ exp.time_
 36 omega   36.00   90.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
 37 omega   90.00  115.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 38 omega  125.00  150.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 39 omega   92.00  124.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
 40 omega  139.00  177.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -180.0000 38

#__ type_ start__ end____ width___ exp.time_
 41 omega   55.00   81.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 42 omega   35.00  107.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -60.0000 72

#__ type_ start__ end____ width___ exp.time_
 43 omega   76.00  115.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
 44 omega   80.00  121.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  150.0000 41

#__ type_ start__ end____ width___ exp.time_
 45 omega  135.00  167.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  150.0000 32

#__ type_ start__ end____ width___ exp.time_
 46 omega  104.00  131.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 47 omega  152.00  178.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 48 omega   89.00  114.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 49 omega   97.00  123.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 50 omega  150.00  175.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 51 omega   49.00   99.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   30.0000 50

#__ type_ start__ end____ width___ exp.time_
 52 omega   60.00  104.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -180.0000 44

#__ type_ start__ end____ width___ exp.time_
 53 omega   39.00   64.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 54 omega   57.00   83.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 55 omega   43.00   98.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 55

#__ type_ start__ end____ width___ exp.time_
 56 omega   37.00   63.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 57 omega   82.00  107.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 58 omega   49.00   81.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -150.0000 32

#__ type_ start__ end____ width___ exp.time_
 59 omega   69.00   94.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 60 omega  123.00  173.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000   60.0000 50

#__ type_ start__ end____ width___ exp.time_
 61 omega  108.00  135.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 62 omega  153.00  178.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 63 omega   74.00   99.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -64.0000   61.8738 25

#__ type_ start__ end____ width___ exp.time_
 64 omega   35.00   86.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -26.0000  106.6766 51
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0221222000
_diffrn_orient_matrix_UB_12      0.1784040000
_diffrn_orient_matrix_UB_13      0.0050859000
_diffrn_orient_matrix_UB_21      0.0771199000
_diffrn_orient_matrix_UB_22      0.0308962000
_diffrn_orient_matrix_UB_23      0.0368645000
_diffrn_orient_matrix_UB_31      0.0445170000
_diffrn_orient_matrix_UB_32      0.0344643000
_diffrn_orient_matrix_UB_33      -0.0593819000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2818
_reflns_number_total             3225
_reflns_odcompleteness_completeness 94.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_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 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0569
_refine_ls_restrained_S_all      1.032
_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)+(0.0676P)²+4.6861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1223
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C6(H6), C7(H7), C10(H10)
2.b X=CH2 refined with riding coordinates:
 N3(H3A,H3B), N2(H2A,H2B)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C3(H3C,H3D,H3E)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
S1 S 0.51772(3) 0.14877(5) 0.58693(2) 0.01466(14) Uani 1 1 d . . . . .
O1 O 0.67766(8) 0.45819(17) 0.48075(6) 0.0179(3) Uani 1 1 d . . . . .
F3 F 0.54947(8) 0.27652(19) 0.69285(6) 0.0315(3) Uani 1 1 d . . . . .
C11 C 0.48935(12) 0.2685(2) 0.65286(9) 0.0186(4) Uani 1 1 d . . . . .
F2 F 0.47128(10) 0.41738(17) 0.63608(7) 0.0362(3) Uani 1 1 d . . . . .
C5 C 0.66988(12) 0.2302(2) 0.34075(8) 0.0161(4) Uani 1 1 d . . . . .
C9 C 0.76397(14) 0.1177(3) 0.27081(10) 0.0236(4) Uani 1 1 d . . . . .
H9 H 0.8172 0.0915 0.2607 0.028 Uiso 1 1 calc R . . . .
C8 C 0.70216(15) 0.0824(3) 0.23020(9) 0.0242(4) Uani 1 1 d . . . . .
H8 H 0.7132 0.0302 0.1929 0.029 Uiso 1 1 calc R . . . .
C6 C 0.60791(13) 0.1974(3) 0.29944(9) 0.0215(4) Uani 1 1 d . . . . .
H6 H 0.5547 0.2257 0.3090 0.026 Uiso 1 1 calc R . . . .
N1 N 0.70691(10) 0.3979(2) 0.42228(7) 0.0173(3) Uani 1 1 d . . . . .
N4 N 0.71161(10) 0.6067(2) 0.56172(7) 0.0179(3) Uani 1 1 d . . . . .
N3 N 0.81048(10) 0.5104(2) 0.49803(7) 0.0181(3) Uani 1 1 d . . . . .
H3A H 0.8483 0.5553 0.5203 0.022 Uiso 1 1 calc R . . . .
H3B H 0.8229 0.4552 0.4654 0.022 Uiso 1 1 calc R . . . .
C2 C 0.73543(12) 0.5260(2) 0.51351(8) 0.0150(4) Uani 1 1 d . . . . .
C1 C 0.65168(12) 0.3028(2) 0.40091(8) 0.0155(4) Uani 1 1 d . . . . .
C4 C 0.76996(13) 0.6751(3) 0.60444(9) 0.0228(4) Uani 1 1 d . . . . .
H4A H 0.8144 0.6002 0.6101 0.034 Uiso 1 1 calc GR . . . .
H4B H 0.7445 0.6944 0.6436 0.034 Uiso 1 1 calc GR . . . .
H4C H 0.7900 0.7763 0.5882 0.034 Uiso 1 1 calc GR . . . .
C3 C 0.62707(13) 0.6272(3) 0.57599(10) 0.0230(4) Uani 1 1 d . . . . .
H3C H 0.5944 0.5963 0.5407 0.035 Uiso 1 1 calc GR . . . .
H3D H 0.6168 0.7395 0.5861 0.035 Uiso 1 1 calc GR . . . .
H3E H 0.6136 0.5595 0.6108 0.035 Uiso 1 1 calc GR . . . .
C7 C 0.62448(14) 0.1232(3) 0.24424(9) 0.0251(5) Uani 1 1 d . . . . .
H7 H 0.5825 0.1006 0.2162 0.030 Uiso 1 1 calc R . . . .
C10 C 0.74814(12) 0.1914(2) 0.32622(9) 0.0194(4) Uani 1 1 d . . . . .
H10 H 0.7904 0.2150 0.3539 0.023 Uiso 1 1 calc R . . . .
O2 O 0.45037(9) 0.1646(2) 0.54562(7) 0.0243(3) Uani 1 1 d . . . . .
F1 F 0.42662(8) 0.20658(18) 0.68024(5) 0.0293(3) Uani 1 1 d . . . . .
O3 O 0.52910(9) -0.01020(18) 0.61177(7) 0.0233(3) Uani 1 1 d . . . . .
O4 O 0.58953(9) 0.22550(18) 0.56635(6) 0.0206(3) Uani 1 1 d . . . . .
N2 N 0.58211(10) 0.2677(2) 0.42715(7) 0.0177(3) Uani 1 1 d . . . . .
H2A H 0.5701 0.3106 0.4624 0.021 Uiso 1 1 calc R . . . .
H2B H 0.5485 0.2018 0.4091 0.021 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C11 1.830(2) . ?
S1 O2 1.4471(14) . ?
S1 O3 1.4486(15) . ?
S1 O4 1.4435(15) . ?
O1 N1 1.471(2) . ?
O1 C2 1.328(2) . ?
F3 C11 1.332(2) . ?
C11 F2 1.332(3) . ?
C11 F1 1.325(2) . ?
C5 C6 1.399(3) . ?
C5 C1 1.491(3) . ?
C5 C10 1.394(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.392(3) . ?
C9 C10 1.394(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.387(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.394(3) . ?
N1 C1 1.304(3) . ?
N4 C2 1.323(3) . ?
N4 C4 1.464(2) . ?
N4 C3 1.467(3) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N3 C2 1.316(3) . ?
C1 N2 1.342(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C3 H3C 0.9800 . ?
C3 H3D 0.9800 . ?
C3 H3E 0.9800 . ?
C7 H7 0.9500 . ?
C10 H10 0.9500 . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?

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 S1 C11 103.78(9) . . ?
O2 S1 O3 114.75(9) . . ?
O3 S1 C11 103.73(9) . . ?
O4 S1 C11 103.44(9) . . ?
O4 S1 O2 114.28(9) . . ?
O4 S1 O3 114.80(9) . . ?
C2 O1 N1 111.76(14) . . ?
F3 C11 S1 110.38(14) . . ?
F3 C11 F2 107.68(17) . . ?
F2 C11 S1 110.62(14) . . ?
F1 C11 S1 111.29(14) . . ?
F1 C11 F3 108.63(16) . . ?
F1 C11 F2 108.13(17) . . ?
C6 C5 C1 119.78(18) . . ?
C10 C5 C6 120.03(18) . . ?
C10 C5 C1 120.17(17) . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 C9 120.00(19) . . ?
C7 C8 H8 120.0 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.8(2) . . ?
C7 C6 H6 120.1 . . ?
C1 N1 O1 106.26(15) . . ?
C2 N4 C4 120.43(17) . . ?
C2 N4 C3 122.28(17) . . ?
C4 N4 C3 117.25(16) . . ?
H3A N3 H3B 120.0 . . ?
C2 N3 H3A 120.0 . . ?
C2 N3 H3B 120.0 . . ?
N4 C2 O1 115.23(17) . . ?
N3 C2 O1 120.85(17) . . ?
N3 C2 N4 123.92(17) . . ?
N1 C1 C5 114.53(17) . . ?
N1 C1 N2 126.66(17) . . ?
N2 C1 C5 118.81(17) . . ?
N4 C4 H4A 109.5 . . ?
N4 C4 H4B 109.5 . . ?
N4 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N4 C3 H3C 109.5 . . ?
N4 C3 H3D 109.5 . . ?
N4 C3 H3E 109.5 . . ?
H3C C3 H3D 109.5 . . ?
H3C C3 H3E 109.5 . . ?
H3D C3 H3E 109.5 . . ?
C8 C7 C6 120.14(19) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C5 C10 H10 120.2 . . ?
C9 C10 C5 119.60(18) . . ?
C9 C10 H10 120.2 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

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
O1 N1 C1 C5 179.30(14) . . . . ?
O1 N1 C1 N2 0.1(3) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C9 C8 C7 C6 -1.0(3) . . . . ?
C8 C9 C10 C5 -0.2(3) . . . . ?
C6 C5 C1 N1 -147.52(19) . . . . ?
C6 C5 C1 N2 31.7(3) . . . . ?
C6 C5 C10 C9 -1.0(3) . . . . ?
N1 O1 C2 N4 169.01(15) . . . . ?
N1 O1 C2 N3 -11.4(2) . . . . ?
C2 O1 N1 C1 165.39(16) . . . . ?
C1 C5 C6 C7 -177.26(18) . . . . ?
C1 C5 C10 C9 177.47(18) . . . . ?
C4 N4 C2 O1 174.63(17) . . . . ?
C4 N4 C2 N3 -4.9(3) . . . . ?
C3 N4 C2 O1 -3.2(3) . . . . ?
C3 N4 C2 N3 177.25(18) . . . . ?
C10 C5 C6 C7 1.2(3) . . . . ?
C10 C5 C1 N1 34.0(3) . . . . ?
C10 C5 C1 N2 -146.73(19) . . . . ?
C10 C9 C8 C7 1.3(3) . . . . ?
O2 S1 C11 F3 -174.44(14) . . . . ?
O2 S1 C11 F2 -55.37(17) . . . . ?
O2 S1 C11 F1 64.86(16) . . . . ?
O3 S1 C11 F3 65.31(16) . . . . ?
O3 S1 C11 F2 -175.62(14) . . . . ?
O3 S1 C11 F1 -55.39(16) . . . . ?
O4 S1 C11 F3 -54.84(16) . . . . ?
O4 S1 C11 F2 64.23(16) . . . . ?
O4 S1 C11 F1 -175.54(14) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 1504005'
_audit_update_record             
;
2016-09-12 deposited with the CCDC.
2017-01-16 downloaded from the CCDC.
;
_audit_creation_date             2016-09-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H22 N4 O6 Zn'
_chemical_formula_sum            'C18 H22 N4 O6 Zn'
_chemical_formula_weight         455.76
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Zn N4 O6 C18 H18'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.955(2)
_cell_length_b                   17.5685(11)
_cell_length_c                   15.782(3)
_cell_angle_alpha                90
_cell_angle_beta                 139.46(4)
_cell_angle_gamma                90
_cell_volume                     2154.3(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11136
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.2832
_cell_measurement_theta_min      2.6062
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.180
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            37536
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.611
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -61.00  -35.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4081 -178.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -90.00   -2.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4081  -57.0000  -30.0000 88

#__ type_ start__ end____ width___ exp.time_
  3 omega  -55.00   51.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4081   19.0000  150.0000 106

#__ type_ start__ end____ width___ exp.time_
  4 omega   32.00   70.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3456 -178.0000  -60.0000 38

#__ type_ start__ end____ width___ exp.time_
  5 omega   21.00   62.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3456  -99.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
  6 omega   -7.00   20.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3456   77.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
  7 omega   62.00   92.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3456   77.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
  8 omega    0.00   37.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3456   77.0000 -150.0000 37

#__ type_ start__ end____ width___ exp.time_
  9 omega    8.00   53.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3456  -99.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 10 omega    3.00   38.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4081   77.0000 -150.0000 35

#__ type_ start__ end____ width___ exp.time_
 11 omega  -73.00   -1.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4081  -57.0000 -150.0000 72

#__ type_ start__ end____ width___ exp.time_
 12 omega  -83.00  -21.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4081  -57.0000   60.0000 62

#__ type_ start__ end____ width___ exp.time_
 13 omega  -87.00   44.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4081    0.0000   60.0000 131

#__ type_ start__ end____ width___ exp.time_
 14 omega  -52.00  -14.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4081   77.0000 -150.0000 38

#__ type_ start__ end____ width___ exp.time_
 15 omega    0.00   58.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3456   77.0000  120.0000 58

#__ type_ start__ end____ width___ exp.time_
 16 omega    7.00   65.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3456  -99.0000    0.0000 58
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0739782000
_diffrn_orient_matrix_UB_12      0.0097946000
_diffrn_orient_matrix_UB_13      -0.0185482000
_diffrn_orient_matrix_UB_21      0.0243598000
_diffrn_orient_matrix_UB_22      -0.0266340000
_diffrn_orient_matrix_UB_23      0.0455857000
_diffrn_orient_matrix_UB_31      0.0477137000
_diffrn_orient_matrix_UB_32      0.0287146000
_diffrn_orient_matrix_UB_33      0.0485754000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4210
_reflns_number_total             4962
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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         0.424
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4962
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0299
_refine_ls_restrained_S_all      1.059
_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)+(0.0291P)²+1.4642P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0748
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C3(H3), C3A(H3A), C7(H7), C4(H4), C6A(H6A), C5A(H5A), C4A(H4A),
 C6(H6), C5(H5)
2.b X=CH2 refined with riding coordinates:
 N2A(H2AA,H2AB), N2(H2A,H2B)
2.c Idealised Me refined as rotating group:
 C9A(H9AA,H9AB,H9AC), C9(H9A,H9B,H9C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 0.43507(2) 0.24817(2) 0.61627(2) 0.01330(7) Uani 1 1 d . . . . .
O3A O 0.27890(15) 0.16996(7) 0.57252(12) 0.0189(3) Uani 1 1 d . . . . .
O3 O 0.35882(16) 0.32672(7) 0.65362(12) 0.0187(3) Uani 1 1 d . . . . .
O1A O 0.72495(16) 0.16940(7) 0.86833(12) 0.0235(3) Uani 1 1 d . . . . .
H1A H 0.6433 0.1382 0.8251 0.035 Uiso 1 1 calc GR . . . .
O2 O 0.2215(2) 0.40940(8) 0.49111(14) 0.0302(3) Uani 1 1 d . . . . .
O1 O 0.20460(18) 0.31260(9) 0.35706(12) 0.0296(3) Uani 1 1 d . . . . .
H1 H 0.2040 0.3458 0.3950 0.044 Uiso 1 1 calc GR . . . .
O2A O 0.46290(17) 0.07649(8) 0.70879(14) 0.0326(3) Uani 1 1 d . . . . .
N1A N 0.68126(18) 0.22746(8) 0.78435(14) 0.0163(3) Uani 1 1 d . . . . .
N1 N 0.35311(19) 0.26606(9) 0.45137(14) 0.0185(3) Uani 1 1 d . . . . .
C2A C 0.7956(2) 0.32750(11) 0.76402(16) 0.0203(4) Uani 1 1 d . . . . .
C2 C 0.5425(2) 0.18265(10) 0.48309(16) 0.0192(4) Uani 1 1 d . . . . .
N2A N 0.9775(2) 0.24351(9) 0.95207(16) 0.0251(4) Uani 1 1 d . . . . .
H2AA H 0.9931 0.2055 0.9965 0.030 Uiso 1 1 calc R . . . .
H2AB H 1.0667 0.2688 0.9837 0.030 Uiso 1 1 calc R . . . .
N2 N 0.3161(2) 0.25529(10) 0.28495(16) 0.0296(4) Uani 1 1 d . . . . .
H2A H 0.2298 0.2878 0.2360 0.035 Uiso 1 1 calc R . . . .
H2B H 0.3492 0.2347 0.2559 0.035 Uiso 1 1 calc R . . . .
C7A C 0.6921(2) 0.38877(11) 0.72684(19) 0.0289(4) Uani 1 1 d . . . . .
H7A H 0.6349 0.3892 0.7471 0.035 Uiso 1 1 calc R . . . .
C1A C 0.8183(2) 0.26278(10) 0.83632(17) 0.0170(3) Uani 1 1 d . . . . .
C8A C 0.3145(2) 0.10217(10) 0.61680(17) 0.0199(4) Uani 1 1 d . . . . .
C8 C 0.2762(2) 0.38909(10) 0.59272(17) 0.0191(4) Uani 1 1 d . . . . .
C3 C 0.6695(2) 0.19255(12) 0.49408(18) 0.0251(4) Uani 1 1 d . . . . .
H3 H 0.6609 0.2336 0.4502 0.030 Uiso 1 1 calc R . . . .
C3A C 0.8818(3) 0.32641(13) 0.73614(19) 0.0324(5) Uani 1 1 d . . . . .
H3A H 0.9548 0.2851 0.7635 0.039 Uiso 1 1 calc R . . . .
C1 C 0.3970(2) 0.23720(10) 0.40393(17) 0.0184(4) Uani 1 1 d . . . . .
C9A C 0.1625(3) 0.05189(12) 0.5500(2) 0.0319(5) Uani 1 1 d . . . . .
H9AA H 0.1154 0.0663 0.5782 0.048 Uiso 1 1 calc GR . . . .
H9AB H 0.1997 -0.0014 0.5731 0.048 Uiso 1 1 calc GR . . . .
H9AC H 0.0737 0.0581 0.4553 0.048 Uiso 1 1 calc GR . . . .
C7 C 0.5543(3) 0.12158(11) 0.5454(2) 0.0312(5) Uani 1 1 d . . . . .
H7 H 0.4672 0.1134 0.5366 0.037 Uiso 1 1 calc R . . . .
C9 C 0.2472(3) 0.43910(11) 0.6523(2) 0.0300(4) Uani 1 1 d . . . . .
H9A H 0.2079 0.4079 0.6774 0.045 Uiso 1 1 calc GR . . . .
H9B H 0.1597 0.4774 0.5886 0.045 Uiso 1 1 calc GR . . . .
H9C H 0.3552 0.4645 0.7297 0.045 Uiso 1 1 calc GR . . . .
C4 C 0.8074(3) 0.14278(14) 0.5687(2) 0.0361(5) Uani 1 1 d . . . . .
H4 H 0.8929 0.1496 0.5755 0.043 Uiso 1 1 calc R . . . .
C6A C 0.6725(3) 0.44948(14) 0.6597(2) 0.0471(7) Uani 1 1 d . . . . .
H6A H 0.6029 0.4918 0.6347 0.057 Uiso 1 1 calc R . . . .
C5A C 0.7553(3) 0.44762(17) 0.6297(2) 0.0577(9) Uani 1 1 d . . . . .
H5A H 0.7405 0.4886 0.5825 0.069 Uiso 1 1 calc R . . . .
C4A C 0.8585(3) 0.38728(18) 0.6673(2) 0.0516(8) Uani 1 1 d . . . . .
H4A H 0.9147 0.3870 0.6461 0.062 Uiso 1 1 calc R . . . .
C6 C 0.6947(4) 0.07236(14) 0.6211(2) 0.0467(7) Uani 1 1 d . . . . .
H6 H 0.7038 0.0309 0.6648 0.056 Uiso 1 1 calc R . . . .
C5 C 0.8206(3) 0.08333(15) 0.6329(2) 0.0451(6) Uani 1 1 d . . . . .
H5 H 0.9164 0.0499 0.6855 0.054 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O3A 1.9725(13) . ?
Zn1 O3 1.9747(12) . ?
Zn1 N1A 1.991(2) . ?
Zn1 N1 1.9890(17) . ?
O3A C8A 1.279(2) . ?
O3 C8 1.287(2) . ?
O1A H1A 0.8400 . ?
O1A N1A 1.4206(18) . ?
O2 C8 1.238(2) . ?
O1 H1 0.8400 . ?
O1 N1 1.421(2) . ?
O2A C8A 1.242(2) . ?
N1A C1A 1.303(2) . ?
N1 C1 1.300(2) . ?
C2A C7A 1.389(3) . ?
C2A C1A 1.483(2) . ?
C2A C3A 1.395(3) . ?
C2 C3 1.401(3) . ?
C2 C1 1.484(3) . ?
C2 C7 1.389(3) . ?
N2A H2AA 0.8800 . ?
N2A H2AB 0.8800 . ?
N2A C1A 1.338(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C1 1.342(2) . ?
C7A H7A 0.9500 . ?
C7A C6A 1.392(3) . ?
C8A C9A 1.511(3) . ?
C8 C9 1.508(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(3) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.394(3) . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
C7 H7 0.9500 . ?
C7 C6 1.395(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C4 H4 0.9500 . ?
C4 C5 1.379(4) . ?
C6A H6A 0.9500 . ?
C6A C5A 1.386(4) . ?
C5A H5A 0.9500 . ?
C5A C4A 1.373(4) . ?
C4A H4A 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.381(4) . ?
C5 H5 0.9500 . ?

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
O3A Zn1 O3 93.58(5) . . ?
O3A Zn1 N1A 112.75(6) . . ?
O3A Zn1 N1 104.95(7) . . ?
O3 Zn1 N1A 106.28(6) . . ?
O3 Zn1 N1 113.58(6) . . ?
N1 Zn1 N1A 122.11(7) . . ?
C8A O3A Zn1 128.59(12) . . ?
C8 O3 Zn1 129.67(11) . . ?
N1A O1A H1A 109.5 . . ?
N1 O1 H1 109.5 . . ?
O1A N1A Zn1 119.82(11) . . ?
C1A N1A Zn1 129.04(12) . . ?
C1A N1A O1A 111.07(15) . . ?
O1 N1 Zn1 116.25(11) . . ?
C1 N1 Zn1 132.76(13) . . ?
C1 N1 O1 110.55(14) . . ?
C7A C2A C1A 120.17(17) . . ?
C7A C2A C3A 120.78(19) . . ?
C3A C2A C1A 119.04(18) . . ?
C3 C2 C1 119.35(17) . . ?
C7 C2 C3 119.43(18) . . ?
C7 C2 C1 121.21(17) . . ?
H2AA N2A H2AB 120.0 . . ?
C1A N2A H2AA 120.0 . . ?
C1A N2A H2AB 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
C2A C7A H7A 120.1 . . ?
C2A C7A C6A 119.7(2) . . ?
C6A C7A H7A 120.1 . . ?
N1A C1A C2A 118.26(16) . . ?
N1A C1A N2A 122.86(17) . . ?
N2A C1A C2A 118.88(16) . . ?
O3A C8A C9A 116.01(17) . . ?
O2A C8A O3A 124.31(17) . . ?
O2A C8A C9A 119.68(17) . . ?
O3 C8 C9 116.10(16) . . ?
O2 C8 O3 124.25(17) . . ?
O2 C8 C9 119.65(17) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.9 . . ?
C2A C3A H3A 120.7 . . ?
C4A C3A C2A 118.6(2) . . ?
C4A C3A H3A 120.7 . . ?
N1 C1 C2 119.66(16) . . ?
N1 C1 N2 122.39(17) . . ?
N2 C1 C2 117.94(16) . . ?
C8A C9A H9AA 109.5 . . ?
C8A C9A H9AB 109.5 . . ?
C8A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C2 C7 H7 120.2 . . ?
C2 C7 C6 119.6(2) . . ?
C6 C7 H7 120.2 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C7A C6A H6A 120.3 . . ?
C5A C6A C7A 119.4(3) . . ?
C5A C6A H6A 120.3 . . ?
C6A C5A H5A 119.6 . . ?
C4A C5A C6A 120.8(2) . . ?
C4A C5A H5A 119.6 . . ?
C3A C4A H4A 119.6 . . ?
C5A C4A C3A 120.7(2) . . ?
C5A C4A H4A 119.6 . . ?
C7 C6 H6 119.7 . . ?
C5 C6 C7 120.5(2) . . ?
C5 C6 H6 119.7 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_3a_OTf4
_database_code_depnum_ccdc_archive 'CCDC 1504006'
_audit_update_record             
;
2017-01-09 deposited with the CCDC.
2017-01-16 downloaded from the CCDC.
;
_audit_creation_date             2017-01-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C16 H25 N4 O7 Zn1.5), 4(C F3 O3 S)'
_chemical_formula_sum            'C36 H50 F12 N8 O26 S4 Zn3'
_chemical_formula_weight         1563.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c12 h9 n3 o3 s1 f3 zn1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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                   9.9101(6)
_cell_length_b                   17.0394(9)
_cell_length_c                   18.2463(6)
_cell_angle_alpha                74.733(4)
_cell_angle_beta                 89.846(4)
_cell_angle_gamma                82.485(5)
_cell_volume                     2945.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5447
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.2150
_cell_measurement_theta_min      5.0300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.890
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0918
_diffrn_reflns_av_unetI/netI     0.0936
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32356
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.499
_diffrn_reflns_theta_min         3.171
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -51.00   27.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   77.0000   60.0000 78

#__ type_ start__ end____ width___ exp.time_
  2 omega  -41.00   22.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -120.0000 63

#__ type_ start__ end____ width___ exp.time_
  3 omega  -34.00   32.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -60.0000 66

#__ type_ start__ end____ width___ exp.time_
  4 omega  -49.00   36.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000    0.0000 85

#__ type_ start__ end____ width___ exp.time_
  5 omega   82.00  127.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  -30.0000 45

#__ type_ start__ end____ width___ exp.time_
  6 omega   11.00   64.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787   57.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
  7 omega   96.00  129.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787 -178.0000  150.0000 33

#__ type_ start__ end____ width___ exp.time_
  8 omega   53.00   90.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -30.0000 37

#__ type_ start__ end____ width___ exp.time_
  9 omega   36.00   66.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 30

#__ type_ start__ end____ width___ exp.time_
 10 omega   53.00   92.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -21.0000   79.8107 39

#__ type_ start__ end____ width___ exp.time_
 11 omega   35.00   88.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
 12 omega   92.00  119.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 13 omega  102.00  172.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   90.0000 70

#__ type_ start__ end____ width___ exp.time_
 14 omega   83.00  177.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   30.0000 94

#__ type_ start__ end____ width___ exp.time_
 15 omega  117.00  152.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
 16 omega   54.00   79.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 17 omega   75.00  104.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  150.0000 29

#__ type_ start__ end____ width___ exp.time_
 18 omega  152.00  178.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   67.00  101.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -150.0000 34

#__ type_ start__ end____ width___ exp.time_
 20 omega   84.00  115.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
 21 omega  126.00  163.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  120.0000 37

#__ type_ start__ end____ width___ exp.time_
 22 omega   72.00  115.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  150.0000 43

#__ type_ start__ end____ width___ exp.time_
 23 omega   68.00  129.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -90.0000 61

#__ type_ start__ end____ width___ exp.time_
 24 omega   43.00   70.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 25 omega   59.00   84.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 26 omega  120.00  178.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
 27 omega  106.00  132.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 28 omega   51.00   78.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 29 omega   48.00  106.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 58

#__ type_ start__ end____ width___ exp.time_
 30 omega   88.00  148.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000    0.0000 60

#__ type_ start__ end____ width___ exp.time_
 31 omega   41.00  143.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000    0.0000 102

#__ type_ start__ end____ width___ exp.time_
 32 omega  111.00  149.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -120.0000 38

#__ type_ start__ end____ width___ exp.time_
 33 omega   81.00  108.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 34 omega   58.00  128.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -120.0000 70

#__ type_ start__ end____ width___ exp.time_
 35 omega   34.00   59.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 36 omega   61.00   88.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 37 omega   87.00  112.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 38 omega   67.00  115.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   90.0000 48

#__ type_ start__ end____ width___ exp.time_
 39 omega  112.00  175.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -120.0000 63

#__ type_ start__ end____ width___ exp.time_
 40 omega   78.00  105.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 41 omega   89.00  144.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -60.0000 55

#__ type_ start__ end____ width___ exp.time_
 42 omega   31.00   65.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  120.0000 34

#__ type_ start__ end____ width___ exp.time_
 43 omega   41.00   66.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1186772000
_diffrn_orient_matrix_UB_12      0.0601600000
_diffrn_orient_matrix_UB_13      0.0166618000
_diffrn_orient_matrix_UB_21      -0.0586662000
_diffrn_orient_matrix_UB_22      -0.0721933000
_diffrn_orient_matrix_UB_23      0.0542336000
_diffrn_orient_matrix_UB_31      0.0841852000
_diffrn_orient_matrix_UB_32      0.0107269000
_diffrn_orient_matrix_UB_33      0.0667042000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7579
_reflns_number_total             11567
_reflns_odcompleteness_completeness 92.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_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 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.664
_refine_diff_density_min         -1.034
_refine_diff_density_rms         0.156
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     813
_refine_ls_number_reflns         11567
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1152
_refine_ls_R_factor_gt           0.0793
_refine_ls_restrained_S_all      1.020
_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)+(0.1329P)²+5.3109P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2065
_refine_ls_wR_factor_ref         0.2495
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Rotating group:
 O5(H5A,H5B), O4B(H4BA,H4BB), O4(H4A,H4B), O5B(H5BA,H5BB), O6(H6A,H6B),
 O6B(H6BA,H6BB)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N1A(H1A), N1B(H1B), N1C(H1C), C3(H3), C3A(H3A), C7B(H7B), C7C(H7C),
 C4(H4), C4A(H4AA), C6B(H6BC), C6C(H6C), C5(H5), C5A(H5AA), C5B(H5BC), C5C(H5C),
  C6(H6), C6A(H6AA), C4B(H4BC), C4C(H4C), C7(H7), C7A(H7A), C3B(H3B), C3C(H3C)
2.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N2A(H2AA,H2AB), N2B(H2BA,H2BB), N2C(H2CA,H2CB)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C9B(H9BA,H9BB,H9BC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Zn1A Zn 0.0000 0.5000 0.0000 0.0239(2) Uani 1 2 d S T P . .
Zn1C Zn 0.5000 0.5000 0.5000 0.0227(2) Uani 1 2 d S T P . .
Zn1 Zn -0.00351(7) 0.50308(5) 0.17232(4) 0.0248(2) Uani 1 1 d . . . . .
Zn1B Zn 0.49649(7) 0.50533(5) 0.32554(4) 0.0248(2) Uani 1 1 d . . . . .
S4 S 0.73131(17) 0.28262(10) 0.18690(11) 0.0398(4) Uani 1 1 d . . . . .
S1 S 0.13597(18) 0.73410(11) 0.29396(12) 0.0436(4) Uani 1 1 d . . . . .
S2 S 0.6475(2) 0.73486(12) 0.10454(16) 0.0575(6) Uani 1 1 d . . . . .
S3 S 0.23999(19) 0.28257(11) 0.40918(12) 0.0458(4) Uani 1 1 d . . . . .
F10 F 0.6057(6) 0.1682(3) 0.2720(3) 0.0624(14) Uani 1 1 d . . . . .
F11 F 0.7095(6) 0.1340(3) 0.1800(3) 0.0632(14) Uani 1 1 d . . . . .
F12 F 0.8208(7) 0.1410(4) 0.2786(4) 0.0806(19) Uani 1 1 d . . . . .
F1 F 0.0042(7) 0.8489(4) 0.1841(4) 0.0773(17) Uani 1 1 d . . . . .
F2 F 0.0752(7) 0.8910(3) 0.2761(3) 0.0692(15) Uani 1 1 d . . . . .
F3 F 0.2160(7) 0.8594(4) 0.1959(4) 0.0739(17) Uani 1 1 d . . . . .
F4 F 0.5719(6) 0.8882(3) 0.0327(3) 0.0696(15) Uani 1 1 d . . . . .
F5 F 0.5147(7) 0.8567(4) 0.1482(4) 0.0784(17) Uani 1 1 d . . . . .
F6 F 0.7229(7) 0.8692(4) 0.1230(4) 0.0774(17) Uani 1 1 d . . . . .
F7 F 0.1329(6) 0.1555(3) 0.3933(3) 0.0645(15) Uani 1 1 d . . . . .
F9 F 0.3488(7) 0.1400(4) 0.3989(5) 0.096(2) Uani 1 1 d . . . . .
F8 F 0.2355(7) 0.1370(3) 0.4996(3) 0.0702(17) Uani 1 1 d . . . . .
O1 O 0.0354(4) 0.5786(3) 0.0658(2) 0.0271(8) Uani 1 1 d . . . . .
O1A O 0.0648(4) 0.4255(3) 0.1049(2) 0.0296(9) Uani 1 1 d . . . . .
O1B O 0.5322(4) 0.5799(3) 0.3962(2) 0.0275(8) Uani 1 1 d . . . . .
O1C O 0.5687(5) 0.4275(3) 0.4304(2) 0.0302(9) Uani 1 1 d . . . . .
O2 O -0.2113(4) 0.5057(3) 0.0271(2) 0.0281(8) Uani 1 1 d . . . . .
O2B O 0.2904(4) 0.5028(3) 0.4709(2) 0.0289(9) Uani 1 1 d . . . . .
O3 O -0.2079(4) 0.5071(3) 0.1494(2) 0.0280(8) Uani 1 1 d . . . . .
O3B O 0.2927(4) 0.5033(3) 0.3479(2) 0.0263(8) Uani 1 1 d . . . . .
O5 O 0.1934(5) 0.4963(4) 0.2146(3) 0.0452(13) Uani 1 1 d . . . . .
H5A H 0.2219 0.5461 0.2044 0.068 Uiso 1 1 d GR . . . .
H5B H 0.2561 0.4644 0.1948 0.068 Uiso 1 1 d GR . . . .
O4B O 0.6898(5) 0.5104(5) 0.2838(3) 0.0599(18) Uani 1 1 d . . . . .
H4BA H 0.7206 0.4670 0.2623 0.090 Uiso 1 1 d GR . . . .
H4BB H 0.7604 0.5074 0.3200 0.090 Uiso 1 1 d GR . . . .
O4 O -0.0350(5) 0.4046(3) 0.2672(2) 0.0380(10) Uani 1 1 d . . . . .
H4A H 0.0430 0.3733 0.2859 0.057 Uiso 1 1 d GR . . . .
H4B H -0.0891 0.3718 0.2548 0.057 Uiso 1 1 d GR . . . .
O5B O 0.4290(7) 0.6028(3) 0.2314(3) 0.0498(14) Uani 1 1 d . . . . .
H5BA H 0.4909 0.6390 0.2162 0.075 Uiso 1 1 d GR . . . .
H5BB H 0.3515 0.6337 0.2408 0.075 Uiso 1 1 d GR . . . .
O6 O -0.0556(7) 0.5988(3) 0.2213(3) 0.0446(12) Uani 1 1 d . . . . .
H6A H -0.1392 0.6254 0.2060 0.067 Uiso 1 1 d GR . . . .
H6B H 0.0018 0.6364 0.2096 0.067 Uiso 1 1 d GR . . . .
O6B O 0.4762(5) 0.4079(3) 0.2764(3) 0.0378(10) Uani 1 1 d . . . . .
H6BA H 0.4222 0.3759 0.3026 0.057 Uiso 1 1 d GR . . . .
H6BB H 0.5549 0.3795 0.2758 0.057 Uiso 1 1 d GR . . . .
O18 O 0.7276(8) 0.3212(4) 0.2467(4) 0.0658(17) Uani 1 1 d . . . . .
O17 O 0.8527(5) 0.2810(4) 0.1463(3) 0.0494(13) Uani 1 1 d . . . . .
O16 O 0.6120(6) 0.3079(4) 0.1339(4) 0.0598(15) Uani 1 1 d . . . . .
O7 O 0.0106(6) 0.7242(4) 0.3347(4) 0.0591(15) Uani 1 1 d . . . . .
O8 O 0.1607(7) 0.6860(4) 0.2412(4) 0.0586(15) Uani 1 1 d . . . . .
O9 O 0.2492(6) 0.7326(4) 0.3425(4) 0.0532(14) Uani 1 1 d . . . . .
O10 O 0.5200(7) 0.7181(6) 0.0819(10) 0.146(6) Uani 1 1 d . . . . .
O12 O 0.7535(6) 0.7306(4) 0.0527(3) 0.0534(14) Uani 1 1 d . . . . .
O11 O 0.6893(11) 0.6948(5) 0.1817(5) 0.110(4) Uani 1 1 d . . . . .
O15 O 0.1178(7) 0.3064(5) 0.4419(8) 0.123(5) Uani 1 1 d . . . . .
O13 O 0.2512(16) 0.3127(6) 0.3315(5) 0.145(6) Uani 1 1 d . . . . .
O14 O 0.3544(7) 0.2891(4) 0.4549(4) 0.0605(16) Uani 1 1 d . . . . .
N1 N 0.0228(5) 0.6618(3) 0.0454(3) 0.0261(10) Uani 1 1 d . . . . .
H1 H -0.0581 0.6909 0.0423 0.031 Uiso 1 1 calc R . . . .
N1A N 0.0966(5) 0.3434(3) 0.1271(3) 0.0252(9) Uani 1 1 d . . . . .
H1A H 0.0318 0.3118 0.1379 0.030 Uiso 1 1 calc R . . . .
N1B N 0.5194(5) 0.6626(3) 0.3775(3) 0.0275(10) Uani 1 1 d . . . . .
H1B H 0.4380 0.6914 0.3679 0.033 Uiso 1 1 calc R . . . .
N1C N 0.6029(5) 0.3456(3) 0.4474(3) 0.0271(10) Uani 1 1 d . . . . .
H1C H 0.5391 0.3135 0.4514 0.032 Uiso 1 1 calc R . . . .
N2 N 0.2499(7) 0.6519(5) 0.0355(6) 0.075(3) Uani 1 1 d . . . . .
H2A H 0.2536 0.5981 0.0486 0.090 Uiso 1 1 calc R . . . .
H2B H 0.3252 0.6744 0.0258 0.090 Uiso 1 1 calc R . . . .
N2A N 0.3203(5) 0.3587(3) 0.1127(3) 0.0347(11) Uani 1 1 d . . . . .
H2AA H 0.2980 0.4123 0.0962 0.042 Uiso 1 1 calc R . . . .
H2AB H 0.4064 0.3371 0.1161 0.042 Uiso 1 1 calc R . . . .
N2B N 0.7475(7) 0.6547(4) 0.3849(5) 0.062(2) Uani 1 1 d . . . . .
H2BA H 0.7539 0.6009 0.3946 0.074 Uiso 1 1 calc R . . . .
H2BB H 0.8217 0.6784 0.3826 0.074 Uiso 1 1 calc R . . . .
N2C N 0.8259(5) 0.3631(4) 0.4540(3) 0.0358(12) Uani 1 1 d . . . . .
H2CA H 0.8021 0.4165 0.4444 0.043 Uiso 1 1 calc R . . . .
H2CB H 0.9124 0.3424 0.4610 0.043 Uiso 1 1 calc R . . . .
C1 C 0.1314(7) 0.6987(4) 0.0303(4) 0.0348(13) Uani 1 1 d . . . . .
C1A C 0.2241(6) 0.3107(4) 0.1324(3) 0.0287(12) Uani 1 1 d . . . . .
C1B C 0.6263(6) 0.6999(4) 0.3737(4) 0.0310(12) Uani 1 1 d . . . . .
C1C C 0.7311(6) 0.3138(4) 0.4580(3) 0.0289(12) Uani 1 1 d . . . . .
C2 C 0.1202(6) 0.7888(4) 0.0047(4) 0.0336(13) Uani 1 1 d . . . . .
C2A C 0.2562(7) 0.2209(4) 0.1592(4) 0.0345(13) Uani 1 1 d . . . . .
C2B C 0.6111(7) 0.7907(4) 0.3556(4) 0.0328(13) Uani 1 1 d . . . . .
C2C C 0.7681(6) 0.2249(4) 0.4740(3) 0.0312(12) Uani 1 1 d . . . . .
C3 C 0.0068(7) 0.8351(4) -0.0391(4) 0.0365(14) Uani 1 1 d . . . . .
H3 H -0.0669 0.8087 -0.0492 0.044 Uiso 1 1 calc R . . . .
C3A C 0.1791(8) 0.1742(5) 0.2143(4) 0.0395(15) Uani 1 1 d . . . . .
H3A H 0.1079 0.2010 0.2376 0.047 Uiso 1 1 calc R . . . .
C7B C 0.4999(8) 0.8341(4) 0.3804(4) 0.0388(14) Uani 1 1 d . . . . .
H7B H 0.4316 0.8058 0.4082 0.047 Uiso 1 1 calc R . . . .
C7C C 0.6920(7) 0.1771(5) 0.4429(4) 0.0396(15) Uani 1 1 d . . . . .
H7C H 0.6164 0.2028 0.4094 0.048 Uiso 1 1 calc R . . . .
C4 C 0.0017(8) 0.9188(5) -0.0674(4) 0.0429(16) Uani 1 1 d . . . . .
H4 H -0.0755 0.9499 -0.0970 0.052 Uiso 1 1 calc R . . . .
C4A C 0.2053(9) 0.0902(5) 0.2349(5) 0.0488(18) Uani 1 1 d . . . . .
H4AA H 0.1509 0.0595 0.2717 0.059 Uiso 1 1 calc R . . . .
C6B C 0.4888(8) 0.9182(5) 0.3647(4) 0.0430(16) Uani 1 1 d . . . . .
H6BC H 0.4127 0.9478 0.3820 0.052 Uiso 1 1 calc R . . . .
C6C C 0.7253(9) 0.0940(5) 0.4603(5) 0.0495(18) Uani 1 1 d . . . . .
H6C H 0.6740 0.0627 0.4376 0.059 Uiso 1 1 calc R . . . .
C5 C 0.1085(9) 0.9574(5) -0.0529(4) 0.0449(16) Uani 1 1 d . . . . .
H5 H 0.1056 1.0151 -0.0727 0.054 Uiso 1 1 calc R . . . .
C5A C 0.3097(9) 0.0493(5) 0.2029(5) 0.0500(19) Uani 1 1 d . . . . .
H5AA H 0.3269 -0.0090 0.2171 0.060 Uiso 1 1 calc R . . . .
C5B C 0.5869(9) 0.9601(5) 0.3242(5) 0.0489(18) Uani 1 1 d . . . . .
H5BC H 0.5784 1.0182 0.3138 0.059 Uiso 1 1 calc R . . . .
C5C C 0.8334(8) 0.0543(5) 0.5108(5) 0.0481(18) Uani 1 1 d . . . . .
H5C H 0.8552 -0.0038 0.5232 0.058 Uiso 1 1 calc R . . . .
C6 C 0.2197(10) 0.9117(6) -0.0094(6) 0.058(2) Uani 1 1 d . . . . .
H6 H 0.2931 0.9383 0.0008 0.070 Uiso 1 1 calc R . . . .
C6A C 0.3880(9) 0.0949(5) 0.1500(5) 0.0503(19) Uani 1 1 d . . . . .
H6AA H 0.4607 0.0673 0.1283 0.060 Uiso 1 1 calc R . . . .
C4B C 0.6956(10) 0.9184(5) 0.2992(6) 0.058(2) Uani 1 1 d . . . . .
H4BC H 0.7626 0.9475 0.2709 0.070 Uiso 1 1 calc R . . . .
C4C C 0.9085(8) 0.1007(5) 0.5427(5) 0.0442(16) Uani 1 1 d . . . . .
H4C H 0.9824 0.0743 0.5772 0.053 Uiso 1 1 calc R . . . .
C7 C 0.2256(9) 0.8287(5) 0.0190(6) 0.056(2) Uani 1 1 d . . . . .
H7 H 0.3028 0.7982 0.0490 0.067 Uiso 1 1 calc R . . . .
C7A C 0.3635(7) 0.1801(5) 0.1274(4) 0.0398(15) Uani 1 1 d . . . . .
H7A H 0.4189 0.2104 0.0909 0.048 Uiso 1 1 calc R . . . .
C3B C 0.7095(8) 0.8339(5) 0.3145(6) 0.0526(19) Uani 1 1 d . . . . .
H3B H 0.7861 0.8051 0.2971 0.063 Uiso 1 1 calc R . . . .
C3C C 0.8765(7) 0.1854(4) 0.5245(4) 0.0377(14) Uani 1 1 d . . . . .
H3C H 0.9287 0.2167 0.5466 0.045 Uiso 1 1 calc R . . . .
C8 C -0.2691(6) 0.5091(4) 0.0873(3) 0.0251(11) Uani 1 1 d . . . . .
C8B C 0.2320(6) 0.5048(3) 0.4089(3) 0.0234(11) Uani 1 1 d . . . . .
C9 C -0.4219(6) 0.5165(4) 0.0870(3) 0.0317(13) Uani 1 1 d . . . . .
H9A H -0.4525 0.5057 0.1394 0.048 Uiso 1 1 calc GR . . . .
H9B H -0.4524 0.4766 0.0628 0.048 Uiso 1 1 calc GR . . . .
H9C H -0.4605 0.5722 0.0586 0.048 Uiso 1 1 calc GR . . . .
C9B C 0.0795(6) 0.5093(4) 0.4070(4) 0.0328(13) Uani 1 1 d . . . . .
H9BA H 0.0384 0.5634 0.4111 0.049 Uiso 1 1 calc GR . . . .
H9BB H 0.0519 0.4667 0.4496 0.049 Uiso 1 1 calc GR . . . .
H9BC H 0.0489 0.5007 0.3590 0.049 Uiso 1 1 calc GR . . . .
C11 C 0.1074(10) 0.8404(5) 0.2333(5) 0.053(2) Uani 1 1 d . . . . .
C12 C 0.6124(9) 0.8437(5) 0.1023(5) 0.053(2) Uani 1 1 d . . . . .
C13 C 0.2425(8) 0.1720(5) 0.4266(4) 0.0448(16) Uani 1 1 d . . . . .
C14 C 0.7177(8) 0.1754(4) 0.2305(5) 0.0443(16) 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
Zn1A Zn1A 0.0000 2_565 ?
Zn1A Zn1 3.1584(7) 2_565 ?
Zn1A O1 2.080(4) . ?
Zn1A O1 2.080(4) 2_565 ?
Zn1A O1A 2.049(4) . ?
Zn1A O1A 2.049(4) 2_565 ?
Zn1A O2 2.146(4) . ?
Zn1A O2 2.146(4) 2_565 ?
Zn1C O1B 2.072(4) 2_666 ?
Zn1C O1B 2.072(4) . ?
Zn1C O1C 2.050(4) 2_666 ?
Zn1C O1C 2.049(4) . ?
Zn1C O2B 2.137(4) 2_666 ?
Zn1C O2B 2.137(4) . ?
Zn1 O1 2.096(4) . ?
Zn1 O1A 2.083(4) . ?
Zn1 O3 2.058(4) . ?
Zn1 O5 2.078(4) . ?
Zn1 O4 2.124(5) . ?
Zn1 O6 2.066(5) . ?
Zn1B O1B 2.094(4) . ?
Zn1B O1C 2.087(4) . ?
Zn1B O3B 2.062(4) . ?
Zn1B O4B 2.063(5) . ?
Zn1B O5B 2.091(5) . ?
Zn1B O6B 2.115(5) . ?
S4 O18 1.413(7) . ?
S4 O17 1.412(6) . ?
S4 O16 1.474(6) . ?
S4 C14 1.813(7) . ?
S1 O7 1.452(7) . ?
S1 O8 1.422(7) . ?
S1 O9 1.425(6) . ?
S1 C11 1.843(8) . ?
S2 O10 1.417(9) . ?
S2 O12 1.420(6) . ?
S2 O11 1.430(9) . ?
S2 C12 1.831(9) . ?
S3 O15 1.408(9) . ?
S3 O13 1.384(9) . ?
S3 O14 1.443(6) . ?
S3 C13 1.823(8) . ?
F10 C14 1.342(10) . ?
F11 C14 1.309(9) . ?
F12 C14 1.318(10) . ?
F1 C11 1.330(11) . ?
F2 C11 1.319(10) . ?
F3 C11 1.305(11) . ?
F4 C12 1.329(11) . ?
F5 C12 1.312(12) . ?
F6 C12 1.321(10) . ?
F7 C13 1.343(10) . ?
F9 C13 1.287(11) . ?
F8 C13 1.313(9) . ?
O1 Zn1A 2.080(4) 2_565 ?
O1 N1 1.357(7) . ?
O1A Zn1A 2.049(4) 2_565 ?
O1A N1A 1.345(7) . ?
O1B N1B 1.348(7) . ?
O1C N1C 1.344(7) . ?
O2 Zn1A 2.146(4) 2_565 ?
O2 C8 1.249(7) . ?
O2B C8B 1.262(7) . ?
O3 C8 1.278(7) . ?
O3B C8B 1.268(7) . ?
O5 H5A 0.9034 . ?
O5 H5B 0.9073 . ?
O4B H4BA 0.9414 . ?
O4B H4BB 0.9507 . ?
O4 H4A 0.8928 . ?
O4 H4B 0.8933 . ?
O5B H5BA 0.9168 . ?
O5B H5BB 0.9149 . ?
O6 H6A 0.8970 . ?
O6 H6B 0.8962 . ?
O6B H6BA 0.8655 . ?
O6B H6BB 0.8645 . ?
N1 H1 0.8800 . ?
N1 C1 1.309(9) . ?
N1A H1A 0.8800 . ?
N1A C1A 1.306(8) . ?
N1B H1B 0.8800 . ?
N1B C1B 1.298(8) . ?
N1C H1C 0.8800 . ?
N1C C1C 1.309(8) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C1 1.319(10) . ?
N2A H2AA 0.8800 . ?
N2A H2AB 0.8800 . ?
N2A C1A 1.325(8) . ?
N2B H2BA 0.8800 . ?
N2B H2BB 0.8800 . ?
N2B C1B 1.325(9) . ?
N2C H2CA 0.8800 . ?
N2C H2CB 0.8800 . ?
N2C C1C 1.330(8) . ?
C1 C2 1.471(10) . ?
C1A C2A 1.470(10) . ?
C1B C2B 1.481(9) . ?
C1C C2C 1.462(9) . ?
C2 C3 1.402(9) . ?
C2 C7 1.379(10) . ?
C2A C3A 1.400(10) . ?
C2A C7A 1.402(10) . ?
C2B C7B 1.389(10) . ?
C2B C3B 1.396(11) . ?
C2C C7C 1.401(9) . ?
C2C C3C 1.394(10) . ?
C3 H3 0.9500 . ?
C3 C4 1.376(11) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.370(11) . ?
C7B H7B 0.9500 . ?
C7B C6B 1.375(11) . ?
C7C H7C 0.9500 . ?
C7C C6C 1.362(11) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(11) . ?
C4A H4AA 0.9500 . ?
C4A C5A 1.386(13) . ?
C6B H6BC 0.9500 . ?
C6B C5B 1.379(12) . ?
C6C H6C 0.9500 . ?
C6C C5C 1.394(12) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(12) . ?
C5A H5AA 0.9500 . ?
C5A C6A 1.377(13) . ?
C5B H5BC 0.9500 . ?
C5B C4B 1.358(14) . ?
C5C H5C 0.9500 . ?
C5C C4C 1.384(12) . ?
C6 H6 0.9500 . ?
C6 C7 1.365(13) . ?
C6A H6AA 0.9500 . ?
C6A C7A 1.390(11) . ?
C4B H4BC 0.9500 . ?
C4B C3B 1.381(12) . ?
C4C H4C 0.9500 . ?
C4C C3C 1.387(10) . ?
C7 H7 0.9500 . ?
C7A H7A 0.9500 . ?
C3B H3B 0.9500 . ?
C3C H3C 0.9500 . ?
C8 C9 1.502(8) . ?
C8B C9B 1.503(8) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C9B H9BA 0.9800 . ?
C9B H9BB 0.9800 . ?
C9B H9BC 0.9800 . ?

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
Zn1A Zn1A Zn1 0(10) 2_565 2_565 ?
Zn1A Zn1A O1 0(10) 2_565 2_565 ?
Zn1A Zn1A O1 0(10) 2_565 . ?
Zn1A Zn1A O1A 0(10) 2_565 2_565 ?
Zn1A Zn1A O1A 0(10) 2_565 . ?
Zn1A Zn1A O2 0(10) 2_565 2_565 ?
Zn1A Zn1A O2 0(10) 2_565 . ?
O1 Zn1A Zn1 138.96(11) . 2_565 ?
O1 Zn1A Zn1 41.04(11) 2_565 2_565 ?
O1 Zn1A O1 180.0 . 2_565 ?
O1 Zn1A O2 87.76(16) . 2_565 ?
O1 Zn1A O2 87.76(16) 2_565 . ?
O1 Zn1A O2 92.24(16) 2_565 2_565 ?
O1 Zn1A O2 92.24(16) . . ?
O1A Zn1A Zn1 139.46(12) . 2_565 ?
O1A Zn1A Zn1 40.54(12) 2_565 2_565 ?
O1A Zn1A O1 105.71(17) . 2_565 ?
O1A Zn1A O1 74.29(17) 2_565 2_565 ?
O1A Zn1A O1 74.29(17) . . ?
O1A Zn1A O1 105.71(17) 2_565 . ?
O1A Zn1A O1A 180.0 . 2_565 ?
O1A Zn1A O2 86.17(16) . 2_565 ?
O1A Zn1A O2 93.83(16) 2_565 2_565 ?
O1A Zn1A O2 86.17(16) 2_565 . ?
O1A Zn1A O2 93.83(16) . . ?
O2 Zn1A Zn1 104.40(10) . 2_565 ?
O2 Zn1A Zn1 75.60(10) 2_565 2_565 ?
O2 Zn1A O2 180.0 . 2_565 ?
O1B Zn1C O1B 180.0 2_666 . ?
O1B Zn1C O2B 87.89(16) 2_666 . ?
O1B Zn1C O2B 92.11(16) . . ?
O1B Zn1C O2B 87.89(16) . 2_666 ?
O1B Zn1C O2B 92.11(16) 2_666 2_666 ?
O1C Zn1C O1B 74.05(17) . . ?
O1C Zn1C O1B 74.05(17) 2_666 2_666 ?
O1C Zn1C O1B 105.95(17) . 2_666 ?
O1C Zn1C O1B 105.95(17) 2_666 . ?
O1C Zn1C O1C 180.00(14) . 2_666 ?
O1C Zn1C O2B 86.13(17) . 2_666 ?
O1C Zn1C O2B 86.13(17) 2_666 . ?
O1C Zn1C O2B 93.87(17) 2_666 2_666 ?
O1C Zn1C O2B 93.87(17) . . ?
O2B Zn1C O2B 180.0 2_666 . ?
O1 Zn1 O4 166.69(17) . . ?
O1A Zn1 O1 73.29(16) . . ?
O1A Zn1 O4 93.54(17) . . ?
O3 Zn1 O1 95.11(16) . . ?
O3 Zn1 O1A 96.19(17) . . ?
O3 Zn1 O5 170.22(17) . . ?
O3 Zn1 O4 84.19(18) . . ?
O3 Zn1 O6 87.6(2) . . ?
O5 Zn1 O1 93.47(19) . . ?
O5 Zn1 O1A 90.8(2) . . ?
O5 Zn1 O4 88.5(2) . . ?
O6 Zn1 O1 94.92(18) . . ?
O6 Zn1 O1A 167.86(19) . . ?
O6 Zn1 O5 87.0(2) . . ?
O6 Zn1 O4 98.33(19) . . ?
O1B Zn1B O6B 166.81(17) . . ?
O1C Zn1B O1B 72.83(16) . . ?
O1C Zn1B O5B 167.98(18) . . ?
O1C Zn1B O6B 93.98(17) . . ?
O3B Zn1B O1B 95.98(16) . . ?
O3B Zn1B O1C 95.87(17) . . ?
O3B Zn1B O4B 170.09(18) . . ?
O3B Zn1B O5B 85.2(2) . . ?
O3B Zn1B O6B 85.13(19) . . ?
O4B Zn1B O1B 91.2(2) . . ?
O4B Zn1B O1C 92.8(2) . . ?
O4B Zn1B O5B 87.4(3) . . ?
O4B Zn1B O6B 89.4(2) . . ?
O5B Zn1B O1B 95.15(18) . . ?
O5B Zn1B O6B 98.04(19) . . ?
O18 S4 O16 115.0(4) . . ?
O18 S4 C14 106.3(4) . . ?
O17 S4 O18 116.8(4) . . ?
O17 S4 O16 110.4(4) . . ?
O17 S4 C14 104.4(4) . . ?
O16 S4 C14 102.3(4) . . ?
O7 S1 C11 104.2(4) . . ?
O8 S1 O7 114.9(4) . . ?
O8 S1 O9 115.3(4) . . ?
O8 S1 C11 103.7(4) . . ?
O9 S1 O7 112.6(4) . . ?
O9 S1 C11 104.4(4) . . ?
O10 S2 O12 115.4(7) . . ?
O10 S2 O11 114.8(8) . . ?
O10 S2 C12 102.6(4) . . ?
O12 S2 O11 113.2(5) . . ?
O12 S2 C12 104.8(4) . . ?
O11 S2 C12 104.2(5) . . ?
O15 S3 O14 109.6(6) . . ?
O15 S3 C13 102.8(4) . . ?
O13 S3 O15 118.0(9) . . ?
O13 S3 O14 115.3(6) . . ?
O13 S3 C13 106.0(5) . . ?
O14 S3 C13 103.2(4) . . ?
Zn1A O1 Zn1A 0.0 2_565 . ?
Zn1A O1 Zn1 98.28(17) 2_565 . ?
Zn1A O1 Zn1 98.28(17) . . ?
N1 O1 Zn1A 128.8(3) . 2_565 ?
N1 O1 Zn1A 128.8(3) . . ?
N1 O1 Zn1 126.7(3) . . ?
Zn1A O1A Zn1A 0.0 2_565 . ?
Zn1A O1A Zn1 99.71(18) 2_565 . ?
Zn1A O1A Zn1 99.71(18) . . ?
N1A O1A Zn1A 129.3(3) . 2_565 ?
N1A O1A Zn1A 129.3(3) . . ?
N1A O1A Zn1 127.3(3) . . ?
Zn1C O1B Zn1B 98.71(17) . . ?
N1B O1B Zn1C 128.4(3) . . ?
N1B O1B Zn1B 127.4(3) . . ?
Zn1C O1C Zn1B 99.66(18) . . ?
N1C O1C Zn1C 129.3(3) . . ?
N1C O1C Zn1B 126.9(3) . . ?
Zn1A O2 Zn1A 0.0 2_565 . ?
C8 O2 Zn1A 130.9(4) . 2_565 ?
C8 O2 Zn1A 130.9(4) . . ?
C8B O2B Zn1C 131.3(4) . . ?
C8 O3 Zn1 129.5(4) . . ?
C8B O3B Zn1B 129.2(4) . . ?
Zn1 O5 H5A 111.9 . . ?
Zn1 O5 H5B 113.4 . . ?
H5A O5 H5B 105.9 . . ?
Zn1B O4B H4BA 113.6 . . ?
Zn1B O4B H4BB 115.9 . . ?
H4BA O4B H4BB 103.0 . . ?
Zn1 O4 H4A 111.9 . . ?
Zn1 O4 H4B 111.5 . . ?
H4A O4 H4B 106.9 . . ?
Zn1B O5B H5BA 113.5 . . ?
Zn1B O5B H5BB 112.1 . . ?
H5BA O5B H5BB 105.4 . . ?
Zn1 O6 H6A 112.0 . . ?
Zn1 O6 H6B 112.2 . . ?
H6A O6 H6B 106.6 . . ?
Zn1B O6B H6BA 110.2 . . ?
Zn1B O6B H6BB 109.7 . . ?
H6BA O6B H6BB 108.7 . . ?
O1 N1 H1 120.1 . . ?
C1 N1 O1 119.8(5) . . ?
C1 N1 H1 120.1 . . ?
O1A N1A H1A 120.2 . . ?
C1A N1A O1A 119.7(5) . . ?
C1A N1A H1A 120.2 . . ?
O1B N1B H1B 119.8 . . ?
C1B N1B O1B 120.4(5) . . ?
C1B N1B H1B 119.8 . . ?
O1C N1C H1C 120.0 . . ?
C1C N1C O1C 119.9(5) . . ?
C1C N1C H1C 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
H2AA N2A H2AB 120.0 . . ?
C1A N2A H2AA 120.0 . . ?
C1A N2A H2AB 120.0 . . ?
H2BA N2B H2BB 120.0 . . ?
C1B N2B H2BA 120.0 . . ?
C1B N2B H2BB 120.0 . . ?
H2CA N2C H2CB 120.0 . . ?
C1C N2C H2CA 120.0 . . ?
C1C N2C H2CB 120.0 . . ?
N1 C1 N2 117.3(6) . . ?
N1 C1 C2 120.9(6) . . ?
N2 C1 C2 121.6(6) . . ?
N1A C1A N2A 119.5(6) . . ?
N1A C1A C2A 118.5(6) . . ?
N2A C1A C2A 122.0(6) . . ?
N1B C1B N2B 118.1(6) . . ?
N1B C1B C2B 120.2(6) . . ?
N2B C1B C2B 121.7(6) . . ?
N1C C1C N2C 119.2(6) . . ?
N1C C1C C2C 119.8(6) . . ?
N2C C1C C2C 121.0(6) . . ?
C3 C2 C1 120.8(6) . . ?
C7 C2 C1 120.4(6) . . ?
C7 C2 C3 118.7(7) . . ?
C3A C2A C1A 121.6(6) . . ?
C3A C2A C7A 118.7(7) . . ?
C7A C2A C1A 119.7(6) . . ?
C7B C2B C1B 120.5(6) . . ?
C7B C2B C3B 118.9(7) . . ?
C3B C2B C1B 120.6(6) . . ?
C7C C2C C1C 121.3(6) . . ?
C3C C2C C1C 120.1(6) . . ?
C3C C2C C7C 118.6(6) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(7) . . ?
C4 C3 H3 119.8 . . ?
C2A C3A H3A 119.7 . . ?
C4A C3A C2A 120.6(7) . . ?
C4A C3A H3A 119.7 . . ?
C2B C7B H7B 120.1 . . ?
C6B C7B C2B 119.9(7) . . ?
C6B C7B H7B 120.1 . . ?
C2C C7C H7C 119.7 . . ?
C6C C7C C2C 120.6(7) . . ?
C6C C7C H7C 119.7 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0(7) . . ?
C5 C4 H4 120.0 . . ?
C3A C4A H4AA 119.4 . . ?
C3A C4A C5A 121.1(8) . . ?
C5A C4A H4AA 119.4 . . ?
C7B C6B H6BC 119.7 . . ?
C7B C6B C5B 120.6(7) . . ?
C5B C6B H6BC 119.7 . . ?
C7C C6C H6C 119.5 . . ?
C7C C6C C5C 121.1(7) . . ?
C5C C6C H6C 119.5 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.5(7) . . ?
C6 C5 H5 120.3 . . ?
C4A C5A H5AA 120.7 . . ?
C6A C5A C4A 118.6(7) . . ?
C6A C5A H5AA 120.7 . . ?
C6B C5B H5BC 120.0 . . ?
C4B C5B C6B 120.1(7) . . ?
C4B C5B H5BC 120.0 . . ?
C6C C5C H5C 120.5 . . ?
C4C C5C C6C 118.9(7) . . ?
C4C C5C H5C 120.5 . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 120.9(8) . . ?
C7 C6 H6 119.5 . . ?
C5A C6A H6AA 119.1 . . ?
C5A C6A C7A 121.8(8) . . ?
C7A C6A H6AA 119.1 . . ?
C5B C4B H4BC 119.8 . . ?
C5B C4B C3B 120.4(8) . . ?
C3B C4B H4BC 119.8 . . ?
C5C C4C H4C 119.8 . . ?
C5C C4C C3C 120.4(7) . . ?
C3C C4C H4C 119.8 . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.5(8) . . ?
C6 C7 H7 119.8 . . ?
C2A C7A H7A 120.4 . . ?
C6A C7A C2A 119.2(8) . . ?
C6A C7A H7A 120.4 . . ?
C2B C3B H3B 119.9 . . ?
C4B C3B C2B 120.1(8) . . ?
C4B C3B H3B 119.9 . . ?
C2C C3C H3C 119.8 . . ?
C4C C3C C2C 120.4(7) . . ?
C4C C3C H3C 119.8 . . ?
O2 C8 O3 124.8(5) . . ?
O2 C8 C9 118.0(5) . . ?
O3 C8 C9 117.3(5) . . ?
O2B C8B O3B 124.7(5) . . ?
O2B C8B C9B 117.8(5) . . ?
O3B C8B C9B 117.5(5) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8B C9B H9BA 109.5 . . ?
C8B C9B H9BB 109.5 . . ?
C8B C9B H9BC 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
F1 C11 S1 109.9(6) . . ?
F2 C11 S1 109.2(6) . . ?
F2 C11 F1 108.2(8) . . ?
F3 C11 S1 110.9(6) . . ?
F3 C11 F1 109.1(8) . . ?
F3 C11 F2 109.5(7) . . ?
F4 C12 S2 110.2(7) . . ?
F5 C12 S2 111.4(6) . . ?
F5 C12 F4 107.3(7) . . ?
F5 C12 F6 108.6(8) . . ?
F6 C12 S2 110.2(6) . . ?
F6 C12 F4 109.1(7) . . ?
F7 C13 S3 110.4(5) . . ?
F9 C13 S3 110.9(6) . . ?
F9 C13 F7 107.5(8) . . ?
F9 C13 F8 111.0(8) . . ?
F8 C13 S3 110.9(6) . . ?
F8 C13 F7 106.0(7) . . ?
F10 C14 S4 110.5(5) . . ?
F11 C14 S4 112.1(6) . . ?
F11 C14 F10 107.4(6) . . ?
F11 C14 F12 110.0(7) . . ?
F12 C14 S4 111.0(6) . . ?
F12 C14 F10 105.6(7) . . ?

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
Zn1A O1 N1 C1 -101.4(6) 2_565 . . . ?
Zn1A O1 N1 C1 -101.4(6) . . . . ?
Zn1A O1A N1A C1A 99.7(5) . . . . ?
Zn1A O1A N1A C1A 99.7(5) 2_565 . . . ?
Zn1A O2 C8 O3 -2.4(9) 2_565 . . . ?
Zn1A O2 C8 O3 -2.4(9) . . . . ?
Zn1A O2 C8 C9 177.2(4) 2_565 . . . ?
Zn1A O2 C8 C9 177.2(4) . . . . ?
Zn1C O1B N1B C1B 101.4(6) . . . . ?
Zn1C O1C N1C C1C -99.7(6) . . . . ?
Zn1C O2B C8B O3B 1.9(9) . . . . ?
Zn1C O2B C8B C9B -178.0(4) . . . . ?
Zn1 O1 N1 C1 112.6(5) . . . . ?
Zn1 O1A N1A C1A -106.4(5) . . . . ?
Zn1 O3 C8 O2 3.0(9) . . . . ?
Zn1 O3 C8 C9 -176.7(4) . . . . ?
Zn1B O1B N1B C1B -110.7(5) . . . . ?
Zn1B O1C N1C C1C 107.6(5) . . . . ?
Zn1B O3B C8B O2B -4.5(9) . . . . ?
Zn1B O3B C8B C9B 175.4(4) . . . . ?
O1 N1 C1 N2 0.4(10) . . . . ?
O1 N1 C1 C2 177.2(5) . . . . ?
O1A N1A C1A N2A -2.9(8) . . . . ?
O1A N1A C1A C2A 178.0(5) . . . . ?
O1B N1B C1B N2B 3.3(9) . . . . ?
O1B N1B C1B C2B -178.0(5) . . . . ?
O1C N1C C1C N2C 2.1(8) . . . . ?
O1C N1C C1C C2C -178.1(5) . . . . ?
O18 S4 C14 F10 55.4(7) . . . . ?
O18 S4 C14 F11 175.2(6) . . . . ?
O18 S4 C14 F12 -61.4(8) . . . . ?
O17 S4 C14 F10 179.4(5) . . . . ?
O17 S4 C14 F11 -60.8(7) . . . . ?
O17 S4 C14 F12 62.6(7) . . . . ?
O16 S4 C14 F10 -65.6(6) . . . . ?
O16 S4 C14 F11 54.2(7) . . . . ?
O16 S4 C14 F12 177.7(7) . . . . ?
O7 S1 C11 F1 -62.7(7) . . . . ?
O7 S1 C11 F2 55.8(8) . . . . ?
O7 S1 C11 F3 176.6(6) . . . . ?
O8 S1 C11 F1 57.9(7) . . . . ?
O8 S1 C11 F2 176.4(6) . . . . ?
O8 S1 C11 F3 -62.8(7) . . . . ?
O9 S1 C11 F1 178.9(6) . . . . ?
O9 S1 C11 F2 -62.6(7) . . . . ?
O9 S1 C11 F3 58.2(7) . . . . ?
O10 S2 C12 F4 -60.0(9) . . . . ?
O10 S2 C12 F5 58.9(10) . . . . ?
O10 S2 C12 F6 179.5(9) . . . . ?
O12 S2 C12 F4 60.9(7) . . . . ?
O12 S2 C12 F5 179.8(6) . . . . ?
O12 S2 C12 F6 -59.6(8) . . . . ?
O11 S2 C12 F4 -179.9(7) . . . . ?
O11 S2 C12 F5 -61.0(8) . . . . ?
O11 S2 C12 F6 59.6(9) . . . . ?
O15 S3 C13 F7 60.1(8) . . . . ?
O15 S3 C13 F9 179.1(9) . . . . ?
O15 S3 C13 F8 -57.0(9) . . . . ?
O13 S3 C13 F7 -64.3(9) . . . . ?
O13 S3 C13 F9 54.7(10) . . . . ?
O13 S3 C13 F8 178.6(9) . . . . ?
O14 S3 C13 F7 174.1(6) . . . . ?
O14 S3 C13 F9 -66.9(8) . . . . ?
O14 S3 C13 F8 56.9(7) . . . . ?
N1 C1 C2 C3 -31.9(10) . . . . ?
N1 C1 C2 C7 152.6(8) . . . . ?
N1A C1A C2A C3A -34.8(8) . . . . ?
N1A C1A C2A C7A 143.0(6) . . . . ?
N1B C1B C2B C7B 34.0(9) . . . . ?
N1B C1B C2B C3B -147.1(7) . . . . ?
N1C C1C C2C C7C 32.8(9) . . . . ?
N1C C1C C2C C3C -143.6(6) . . . . ?
N2 C1 C2 C3 144.8(8) . . . . ?
N2 C1 C2 C7 -30.8(12) . . . . ?
N2A C1A C2A C3A 146.0(6) . . . . ?
N2A C1A C2A C7A -36.2(9) . . . . ?
N2B C1B C2B C7B -147.3(8) . . . . ?
N2B C1B C2B C3B 31.6(11) . . . . ?
N2C C1C C2C C7C -147.4(7) . . . . ?
N2C C1C C2C C3C 36.3(9) . . . . ?
C1 C2 C3 C4 -175.3(7) . . . . ?
C1 C2 C7 C6 175.2(9) . . . . ?
C1A C2A C3A C4A 175.7(6) . . . . ?
C1A C2A C7A C6A -176.3(6) . . . . ?
C1B C2B C7B C6B 178.5(6) . . . . ?
C1B C2B C3B C4B -178.8(8) . . . . ?
C1C C2C C7C C6C -178.0(7) . . . . ?
C1C C2C C3C C4C 177.1(6) . . . . ?
C2 C3 C4 C5 0.1(11) . . . . ?
C2A C3A C4A C5A 1.1(11) . . . . ?
C2B C7B C6B C5B 0.3(11) . . . . ?
C2C C7C C6C C5C 1.7(13) . . . . ?
C3 C2 C7 C6 -0.5(14) . . . . ?
C3 C4 C5 C6 -0.4(12) . . . . ?
C3A C2A C7A C6A 1.6(10) . . . . ?
C3A C4A C5A C6A 0.5(12) . . . . ?
C7B C2B C3B C4B 0.1(13) . . . . ?
C7B C6B C5B C4B 0.2(12) . . . . ?
C7C C2C C3C C4C 0.7(10) . . . . ?
C7C C6C C5C C4C -0.9(13) . . . . ?
C4 C5 C6 C7 0.3(14) . . . . ?
C4A C5A C6A C7A -0.9(12) . . . . ?
C6B C5B C4B C3B -0.5(14) . . . . ?
C6C C5C C4C C3C 0.0(12) . . . . ?
C5 C6 C7 C2 0.2(16) . . . . ?
C5A C6A C7A C2A -0.1(11) . . . . ?
C5B C4B C3B C2B 0.4(15) . . . . ?
C5C C4C C3C C2C 0.1(11) . . . . ?
C7 C2 C3 C4 0.4(11) . . . . ?
C7A C2A C3A C4A -2.1(10) . . . . ?
C3B C2B C7B C6B -0.4(11) . . . . ?
C3C C2C C7C C6C -1.6(11) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
