# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Wen-Xiong Zhang'
_publ_contact_author_email       'WX ZHANG@PKU.EDU.CN'

_publ_section_title              
;
Zn(OTf)2-catalyzed addition of amines to carbodiimides:
efficient synthesis of guanidines and unpredicted formation of Zn-N amido
species
;
loop_
_publ_author_name
'Wen-Xiong Zhang.'
'Jie Guang.'
'Dongzhen Li.'
'Yang Wang.'
'Zhenfeng Xi.'

# Attachment '22.cif'

data_22
_database_code_depnum_ccdc_archive 'CCDC 741355'
#TrackingRef '22.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H28 N3, C F3 O3 S'
_chemical_formula_sum            'C17 H28 F3 N3 O3 S'
_chemical_formula_weight         411.48

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   16.419(3)
_cell_length_b                   12.458(3)
_cell_length_c                   10.520(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2151.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    573
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9435
_exptl_absorpt_correction_T_max  0.9749
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16883
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4604
_reflns_number_gt                4315
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0375P)^2^+0.6163P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_number_reflns         4604
_refine_ls_number_parameters     244
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.0977
_refine_ls_wR_factor_gt          0.0945
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.12695(3) 0.20439(4) 0.50146(6) 0.03428(13) Uani 1 1 d . . .
F1 F 0.08073(12) 0.33631(14) 0.32183(17) 0.0665(5) Uani 1 1 d . . .
F2 F 0.06907(9) 0.40069(11) 0.51011(19) 0.0586(4) Uani 1 1 d . . .
F3 F 0.18766(10) 0.38692(12) 0.4239(2) 0.0678(5) Uani 1 1 d . . .
O1 O 0.04446(8) 0.16702(12) 0.51641(17) 0.0387(4) Uani 1 1 d . . .
O2 O 0.17238(9) 0.14895(13) 0.40420(18) 0.0428(4) Uani 1 1 d . . .
O3 O 0.16993(10) 0.22249(15) 0.61845(18) 0.0466(4) Uani 1 1 d . . .
N1 N 0.18733(11) 0.93204(15) 0.31185(18) 0.0333(4) Uani 1 1 d . . .
H1 H 0.1654 0.9944 0.3313 0.040 Uiso 1 1 d R . .
N2 N 0.05904(11) 0.89597(15) 0.22783(19) 0.0356(4) Uani 1 1 d . . .
H2 H 0.0371 0.8627 0.1624 0.043 Uiso 1 1 d R . .
N3 N 0.16566(11) 0.77782(15) 0.19463(19) 0.0343(4) Uani 1 1 d . . .
H3 H 0.2184 0.7671 0.2017 0.041 Uiso 1 1 d R . .
C1 C 0.26834(13) 0.90211(17) 0.3495(2) 0.0342(5) Uani 1 1 d . . .
C2 C 0.28125(14) 0.82765(19) 0.4450(2) 0.0388(5) Uani 1 1 d . . .
C3 C 0.36266(17) 0.8073(2) 0.4793(3) 0.0527(7) Uani 1 1 d . . .
H3A H 0.3739 0.7564 0.5442 0.063 Uiso 1 1 calc R . .
C4 C 0.42647(16) 0.8595(3) 0.4207(3) 0.0568(8) Uani 1 1 d . . .
H4A H 0.4808 0.8440 0.4457 0.068 Uiso 1 1 calc R . .
C5 C 0.41240(16) 0.9338(3) 0.3264(3) 0.0543(7) Uani 1 1 d . . .
H5A H 0.4565 0.9696 0.2863 0.065 Uiso 1 1 calc R . .
C6 C 0.33265(15) 0.9555(2) 0.2907(3) 0.0436(6) Uani 1 1 d . . .
H6A H 0.3219 1.0069 0.2261 0.052 Uiso 1 1 calc R . .
C7 C 0.13680(13) 0.86838(17) 0.2430(2) 0.0307(4) Uani 1 1 d . . .
C8 C 0.01898(13) 0.98940(18) 0.2864(2) 0.0343(5) Uani 1 1 d . . .
H8A H 0.0498 1.0095 0.3649 0.041 Uiso 1 1 calc R . .
C9 C 0.02008(18) 1.0842(2) 0.1960(3) 0.0510(7) Uani 1 1 d . . .
H9A H 0.0765 1.1020 0.1743 0.077 Uiso 1 1 calc R . .
H9B H -0.0057 1.1462 0.2369 0.077 Uiso 1 1 calc R . .
H9C H -0.0098 1.0657 0.1184 0.077 Uiso 1 1 calc R . .
C10 C -0.06713(15) 0.9583(2) 0.3243(3) 0.0471(6) Uani 1 1 d . . .
H10A H -0.0652 0.8972 0.3828 0.071 Uiso 1 1 calc R . .
H10B H -0.0981 0.9385 0.2483 0.071 Uiso 1 1 calc R . .
H10C H -0.0936 1.0193 0.3664 0.071 Uiso 1 1 calc R . .
C11 C 0.11817(14) 0.69885(17) 0.1207(2) 0.0353(5) Uani 1 1 d . . .
H11A H 0.0595 0.7058 0.1449 0.042 Uiso 1 1 calc R . .
C12 C 0.12614(15) 0.7209(2) -0.0208(2) 0.0434(6) Uani 1 1 d . . .
H12A H 0.1078 0.7941 -0.0390 0.065 Uiso 1 1 calc R . .
H12B H 0.0925 0.6697 -0.0682 0.065 Uiso 1 1 calc R . .
H12C H 0.1832 0.7130 -0.0464 0.065 Uiso 1 1 calc R . .
C13 C 0.14642(18) 0.5867(2) 0.1541(3) 0.0534(7) Uani 1 1 d . . .
H13A H 0.1400 0.5748 0.2456 0.080 Uiso 1 1 calc R . .
H13B H 0.2039 0.5785 0.1308 0.080 Uiso 1 1 calc R . .
H13C H 0.1137 0.5341 0.1073 0.080 Uiso 1 1 calc R . .
C14 C 0.21306(17) 0.7704(2) 0.5132(3) 0.0530(6) Uani 1 1 d . . .
H14A H 0.1612 0.7895 0.4689 0.064 Uiso 1 1 calc R . .
C15 C 0.2050(2) 0.8062(4) 0.6502(4) 0.0896(13) Uani 1 1 d . . .
H15A H 0.1976 0.8842 0.6532 0.134 Uiso 1 1 calc R . .
H15B H 0.2544 0.7866 0.6972 0.134 Uiso 1 1 calc R . .
H15C H 0.1578 0.7710 0.6890 0.134 Uiso 1 1 calc R . .
C16 C 0.2230(2) 0.6471(3) 0.5047(5) 0.0868(11) Uani 1 1 d . . .
H16A H 0.1778 0.6122 0.5494 0.130 Uiso 1 1 calc R . .
H16B H 0.2746 0.6259 0.5440 0.130 Uiso 1 1 calc R . .
H16C H 0.2227 0.6251 0.4153 0.130 Uiso 1 1 calc R . .
C17 C 0.11595(16) 0.3388(2) 0.4356(3) 0.0450(6) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0291(2) 0.0299(2) 0.0438(3) -0.0044(3) 0.0032(3) -0.00242(19)
F1 0.0939(14) 0.0517(10) 0.0537(11) 0.0099(8) -0.0019(9) 0.0031(9)
F2 0.0605(9) 0.0390(7) 0.0762(11) -0.0084(9) 0.0078(10) 0.0123(6)
F3 0.0631(10) 0.0401(8) 0.1002(14) 0.0045(9) 0.0213(10) -0.0143(7)
O1 0.0273(7) 0.0422(8) 0.0466(10) -0.0021(8) 0.0056(8) -0.0041(6)
O2 0.0333(8) 0.0369(9) 0.0583(12) -0.0130(8) 0.0109(8) -0.0034(7)
O3 0.0367(9) 0.0520(11) 0.0511(11) -0.0071(9) -0.0064(8) -0.0077(8)
N1 0.0348(10) 0.0270(9) 0.0379(10) -0.0037(8) -0.0081(8) 0.0042(7)
N2 0.0340(10) 0.0346(10) 0.0381(11) -0.0094(8) -0.0065(8) 0.0031(8)
N3 0.0292(9) 0.0327(9) 0.0411(11) -0.0072(8) -0.0040(8) 0.0038(7)
C1 0.0366(12) 0.0296(11) 0.0365(13) -0.0067(9) -0.0056(10) 0.0019(9)
C2 0.0388(13) 0.0350(11) 0.0425(13) -0.0064(10) -0.0104(10) 0.0028(9)
C3 0.0544(16) 0.0407(13) 0.063(2) -0.0057(13) -0.0233(14) 0.0107(11)
C4 0.0379(14) 0.0581(16) 0.074(2) -0.0223(16) -0.0122(14) 0.0104(12)
C5 0.0391(14) 0.0637(18) 0.0601(18) -0.0188(16) 0.0000(12) -0.0060(13)
C6 0.0417(13) 0.0445(14) 0.0445(14) -0.0030(11) -0.0025(11) -0.0058(10)
C7 0.0363(11) 0.0281(10) 0.0277(11) -0.0015(8) -0.0034(9) 0.0013(8)
C8 0.0333(12) 0.0300(11) 0.0398(13) -0.0032(9) -0.0005(10) 0.0022(9)
C9 0.0560(16) 0.0369(13) 0.0602(18) 0.0062(12) 0.0061(14) 0.0045(12)
C10 0.0422(14) 0.0448(14) 0.0544(16) -0.0093(12) 0.0121(12) -0.0032(11)
C11 0.0376(12) 0.0294(11) 0.0389(13) -0.0077(9) -0.0021(10) -0.0012(9)
C12 0.0342(12) 0.0565(15) 0.0395(16) -0.0096(11) -0.0021(10) 0.0018(10)
C13 0.0607(17) 0.0327(13) 0.067(2) -0.0029(13) -0.0081(14) -0.0007(12)
C14 0.0564(16) 0.0588(16) 0.0438(15) 0.0151(15) -0.0106(14) -0.0055(12)
C15 0.072(2) 0.133(4) 0.064(2) -0.006(2) 0.0080(18) -0.009(2)
C16 0.118(3) 0.0572(19) 0.086(3) 0.023(2) -0.001(3) -0.0171(18)
C17 0.0463(15) 0.0343(12) 0.0544(17) -0.0023(12) 0.0076(12) -0.0001(10)

_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 O3 1.4365(19) . ?
S1 O1 1.4409(15) . ?
S1 O2 1.4422(18) . ?
S1 C17 1.821(3) . ?
F1 C17 1.329(3) . ?
F2 C17 1.342(3) . ?
F3 C17 1.327(3) . ?
N1 C7 1.357(3) . ?
N1 C1 1.437(3) . ?
N1 H1 0.8800 . ?
N2 C7 1.332(3) . ?
N2 C8 1.472(3) . ?
N2 H2 0.8801 . ?
N3 C7 1.325(3) . ?
N3 C11 1.477(3) . ?
N3 H3 0.8801 . ?
C1 C2 1.384(3) . ?
C1 C6 1.393(3) . ?
C2 C3 1.407(3) . ?
C2 C14 1.509(4) . ?
C3 C4 1.379(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.376(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.389(4) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C8 C9 1.516(3) . ?
C8 C10 1.519(3) . ?
C8 H8A 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C13 1.514(3) . ?
C11 C12 1.520(4) . ?
C11 H11A 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.515(5) . ?
C14 C16 1.547(4) . ?
C14 H14A 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
O3 S1 O1 114.77(11) . . ?
O3 S1 O2 115.40(11) . . ?
O1 S1 O2 114.13(10) . . ?
O3 S1 C17 103.32(12) . . ?
O1 S1 C17 104.20(11) . . ?
O2 S1 C17 102.80(12) . . ?
C7 N1 C1 124.14(18) . . ?
C7 N1 H1 112.9 . . ?
C1 N1 H1 122.9 . . ?
C7 N2 C8 125.61(18) . . ?
C7 N2 H2 111.3 . . ?
C8 N2 H2 121.1 . . ?
C7 N3 C11 125.48(19) . . ?
C7 N3 H3 116.7 . . ?
C11 N3 H3 117.6 . . ?
C2 C1 C6 121.8(2) . . ?
C2 C1 N1 121.1(2) . . ?
C6 C1 N1 117.1(2) . . ?
C1 C2 C3 116.9(2) . . ?
C1 C2 C14 123.3(2) . . ?
C3 C2 C14 119.9(2) . . ?
C4 C3 C2 121.5(3) . . ?
C4 C3 H3A 119.3 . . ?
C2 C3 H3A 119.3 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C4 C5 C6 119.0(3) . . ?
C4 C5 H5A 120.5 . . ?
C6 C5 H5A 120.5 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 H6A 119.9 . . ?
C1 C6 H6A 119.9 . . ?
N3 C7 N2 121.11(19) . . ?
N3 C7 N1 118.93(19) . . ?
N2 C7 N1 119.94(19) . . ?
N2 C8 C9 110.4(2) . . ?
N2 C8 C10 108.92(19) . . ?
C9 C8 C10 112.0(2) . . ?
N2 C8 H8A 108.5 . . ?
C9 C8 H8A 108.5 . . ?
C10 C8 H8A 108.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 C13 109.4(2) . . ?
N3 C11 C12 110.49(19) . . ?
C13 C11 C12 111.5(2) . . ?
N3 C11 H11A 108.5 . . ?
C13 C11 H11A 108.5 . . ?
C12 C11 H11A 108.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 C14 C15 112.2(3) . . ?
C2 C14 C16 111.4(3) . . ?
C15 C14 C16 110.9(3) . . ?
C2 C14 H14A 107.4 . . ?
C15 C14 H14A 107.4 . . ?
C16 C14 H14A 107.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F3 C17 F1 108.2(2) . . ?
F3 C17 F2 107.7(2) . . ?
F1 C17 F2 106.8(2) . . ?
F3 C17 S1 111.27(18) . . ?
F1 C17 S1 111.37(18) . . ?
F2 C17 S1 111.27(18) . . ?

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
C7 N1 C1 C2 -73.6(3) . . . . ?
C7 N1 C1 C6 109.8(3) . . . . ?
C6 C1 C2 C3 -0.7(4) . . . . ?
N1 C1 C2 C3 -177.1(2) . . . . ?
C6 C1 C2 C14 178.4(2) . . . . ?
N1 C1 C2 C14 2.0(4) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C14 C2 C3 C4 -178.8(3) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C2 C1 C6 C5 0.8(4) . . . . ?
N1 C1 C6 C5 177.3(2) . . . . ?
C11 N3 C7 N2 0.1(4) . . . . ?
C11 N3 C7 N1 178.3(2) . . . . ?
C8 N2 C7 N3 174.4(2) . . . . ?
C8 N2 C7 N1 -3.8(3) . . . . ?
C1 N1 C7 N3 -7.8(3) . . . . ?
C1 N1 C7 N2 170.4(2) . . . . ?
C7 N2 C8 C9 94.7(3) . . . . ?
C7 N2 C8 C10 -142.0(2) . . . . ?
C7 N3 C11 C13 -143.1(2) . . . . ?
C7 N3 C11 C12 93.8(3) . . . . ?
C1 C2 C14 C15 -110.6(3) . . . . ?
C3 C2 C14 C15 68.4(4) . . . . ?
C1 C2 C14 C16 124.4(3) . . . . ?
C3 C2 C14 C16 -56.6(4) . . . . ?
O3 S1 C17 F3 55.7(2) . . . . ?
O1 S1 C17 F3 175.98(19) . . . . ?
O2 S1 C17 F3 -64.7(2) . . . . ?
O3 S1 C17 F1 176.57(18) . . . . ?
O1 S1 C17 F1 -63.2(2) . . . . ?
O2 S1 C17 F1 56.2(2) . . . . ?
O3 S1 C17 F2 -64.3(2) . . . . ?
O1 S1 C17 F2 55.9(2) . . . . ?
O2 S1 C17 F2 175.27(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.88 2.08 2.882(2) 151.9 1_565
N2 H2 O1 0.88 2.07 2.907(2) 158.1 2_564
N3 H3 O3 0.88 2.11 2.899(3) 149.5 4_554

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.037

# Attachment '20.cif'

data_20
_database_code_depnum_ccdc_archive 'CCDC 741356'
#TrackingRef '20.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H68 F12 N4 O14 S4 Zn2'
_chemical_formula_weight         1412.04

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   I4(1)/a

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   35.199(5)
_cell_length_b                   35.199(5)
_cell_length_c                   11.268(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     13960(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    867
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             5824
_exptl_absorpt_coefficient_mu    0.894
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7450
_exptl_absorpt_correction_T_max  0.9160
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            62839
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.16
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6130
_reflns_number_gt                5821
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1300P)^2^+37.5071P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6130
_refine_ls_number_parameters     391
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0644
_refine_ls_wR_factor_ref         0.1999
_refine_ls_wR_factor_gt          0.1956
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.036775(12) 0.424787(12) 1.01376(4) 0.0330(2) Uani 1 1 d . . .
S1 S -0.00141(3) 0.37015(3) 1.21418(9) 0.0388(3) Uani 1 1 d . . .
S2 S 0.04291(3) 0.51397(3) 0.90279(9) 0.0341(3) Uani 1 1 d . . .
F1 F -0.01693(11) 0.30625(11) 1.3177(4) 0.0874(12) Uani 1 1 d . . .
F2 F 0.04192(10) 0.32169(11) 1.3228(4) 0.0863(12) Uani 1 1 d . . .
F3 F 0.01743(10) 0.30099(9) 1.1605(4) 0.0784(10) Uani 1 1 d . . .
F4 F 0.05985(10) 0.52031(12) 0.6791(3) 0.0794(10) Uani 1 1 d . . .
F5 F 0.08372(10) 0.56367(9) 0.7902(4) 0.0768(10) Uani 1 1 d . . .
F6 F 0.10721(8) 0.50754(9) 0.7905(3) 0.0649(8) Uani 1 1 d . . .
O1 O 0.03076(8) 0.38040(9) 1.1388(3) 0.0414(7) Uani 1 1 d . . .
O2 O -0.03643(9) 0.36641(9) 1.1492(3) 0.0457(7) Uani 1 1 d . . .
O3 O -0.00282(12) 0.39043(11) 1.3227(3) 0.0648(10) Uani 1 1 d . . .
O4 O 0.04054(8) 0.47288(8) 0.8905(2) 0.0372(6) Uani 1 1 d . . .
O5 O 0.00799(8) 0.53353(8) 0.8757(3) 0.0397(7) Uani 1 1 d . . .
O6 O 0.06173(8) 0.52644(8) 1.0095(3) 0.0420(7) Uani 1 1 d . . .
O7 O 0.07728(8) 0.39724(8) 0.9177(2) 0.0397(7) Uani 1 1 d . . .
N1 N -0.01310(9) 0.40690(9) 0.9301(3) 0.0350(7) Uani 1 1 d . . .
H1A H -0.0275 0.3940 0.9851 0.042 Uiso 1 1 calc R . .
H1B H -0.0266 0.4282 0.9086 0.042 Uiso 1 1 calc R . .
N2 N 0.07042(10) 0.45295(10) 1.1409(3) 0.0386(8) Uani 1 1 d . . .
H2A H 0.0677 0.4786 1.1284 0.046 Uiso 1 1 calc R . .
H2B H 0.0603 0.4478 1.2144 0.046 Uiso 1 1 calc R . .
C1 C -0.00965(11) 0.38320(12) 0.8271(3) 0.0353(9) Uani 1 1 d . . .
C2 C -0.01406(15) 0.39820(14) 0.7111(4) 0.0500(12) Uani 1 1 d . . .
C3 C -0.00896(18) 0.37342(17) 0.6171(4) 0.0643(15) Uani 1 1 d . . .
H3A H -0.0116 0.3827 0.5383 0.077 Uiso 1 1 calc R . .
C4 C -0.00013(18) 0.33527(17) 0.6346(5) 0.0668(15) Uani 1 1 d . . .
H4A H 0.0032 0.3189 0.5683 0.080 Uiso 1 1 calc R . .
C5 C 0.00372(16) 0.32132(15) 0.7472(5) 0.0563(13) Uani 1 1 d . . .
H5A H 0.0095 0.2952 0.7592 0.068 Uiso 1 1 calc R . .
C6 C -0.00086(13) 0.34512(13) 0.8429(4) 0.0435(10) Uani 1 1 d . . .
H6A H 0.0020 0.3353 0.9209 0.052 Uiso 1 1 calc R . .
C7 C -0.02517(18) 0.43939(15) 0.6916(4) 0.0633(16) Uani 1 1 d . . .
H7A H -0.0171 0.4535 0.7643 0.076 Uiso 1 1 calc R . .
C8 C -0.0686(2) 0.44401(19) 0.6830(8) 0.096(3) Uani 1 1 d . . .
H8A H -0.0805 0.4329 0.7535 0.115 Uiso 1 1 calc R . .
H8B H -0.0779 0.4310 0.6118 0.115 Uiso 1 1 calc R . .
H8C H -0.0749 0.4711 0.6782 0.115 Uiso 1 1 calc R . .
C9 C -0.0034(3) 0.4574(2) 0.5863(7) 0.107(3) Uani 1 1 d . . .
H9A H -0.0112 0.4840 0.5769 0.129 Uiso 1 1 calc R . .
H9B H -0.0091 0.4434 0.5134 0.129 Uiso 1 1 calc R . .
H9C H 0.0240 0.4563 0.6019 0.129 Uiso 1 1 calc R . .
C10 C 0.11041(13) 0.44502(13) 1.1467(4) 0.0439(10) Uani 1 1 d . . .
C11 C 0.12612(16) 0.42175(14) 1.2350(5) 0.0567(13) Uani 1 1 d . B .
C12 C 0.16578(18) 0.41613(19) 1.2283(7) 0.079(2) Uani 1 1 d . . .
H12A H 0.1777 0.3999 1.2843 0.095 Uiso 1 1 calc R . .
C13 C 0.18755(19) 0.4334(2) 1.1433(8) 0.090(2) Uani 1 1 d . . .
H13A H 0.2143 0.4299 1.1443 0.108 Uiso 1 1 calc R . .
C14 C 0.17197(16) 0.4555(2) 1.0580(7) 0.085(2) Uani 1 1 d . . .
H14A H 0.1874 0.4661 0.9974 0.102 Uiso 1 1 calc R . .
C15 C 0.13360(14) 0.46233(18) 1.0601(5) 0.0631(14) Uani 1 1 d . . .
H15A H 0.1226 0.4788 1.0029 0.076 Uiso 1 1 calc R . .
C16 C 0.10318(18) 0.40432(18) 1.3304(6) 0.0749(19) Uani 1 1 d D . .
H16A H 0.0773 0.3993 1.2974 0.090 Uiso 1 1 calc R A 1
C17 C 0.0987(3) 0.4327(3) 1.4341(7) 0.115(3) Uani 1 1 d . B .
H17A H 0.0900 0.4572 1.4033 0.138 Uiso 1 1 calc R . .
H17B H 0.1232 0.4360 1.4739 0.138 Uiso 1 1 calc R . .
H17C H 0.0801 0.4228 1.4909 0.138 Uiso 1 1 calc R . .
C18 C 0.1219(5) 0.3650(3) 1.357(2) 0.083(5) Uani 0.62(4) 1 d PDU B 1
H18A H 0.1243 0.3505 1.2836 0.100 Uiso 0.62(4) 1 calc PR B 1
H18B H 0.1059 0.3509 1.4134 0.100 Uiso 0.62(4) 1 calc PR B 1
H18C H 0.1471 0.3689 1.3921 0.100 Uiso 0.62(4) 1 calc PR B 1
C18' C 0.1103(8) 0.3688(6) 1.407(3) 0.074(7) Uani 0.38(4) 1 d PDU B 2
H18D H 0.0900 0.3664 1.4657 0.111 Uiso 0.38(4) 1 calc PR B 2
H18E H 0.1348 0.3711 1.4469 0.111 Uiso 0.38(4) 1 calc PR B 2
H18F H 0.1104 0.3462 1.3556 0.111 Uiso 0.38(4) 1 calc PR B 2
C19 C 0.01135(15) 0.32213(16) 1.2557(5) 0.0573(13) Uani 1 1 d . . .
C20 C 0.07506(13) 0.52712(13) 0.7827(5) 0.0478(11) Uani 1 1 d . . .
C21 C 0.09710(15) 0.36282(14) 0.9571(4) 0.0492(11) Uani 1 1 d . . .
H21A H 0.0788 0.3428 0.9797 0.059 Uiso 1 1 calc R . .
H21B H 0.1138 0.3683 1.0257 0.059 Uiso 1 1 calc R . .
C22 C 0.1198(2) 0.3510(2) 0.8524(5) 0.092(2) Uani 1 1 d . . .
H22A H 0.1470 0.3563 0.8668 0.110 Uiso 1 1 calc R . .
H22B H 0.1168 0.3234 0.8388 0.110 Uiso 1 1 calc R . .
C23 C 0.1075(2) 0.3710(2) 0.7532(6) 0.091(2) Uani 1 1 d . . .
H23A H 0.0898 0.3552 0.7060 0.109 Uiso 1 1 calc R . .
H23B H 0.1295 0.3778 0.7024 0.109 Uiso 1 1 calc R . .
C24 C 0.08803(15) 0.40602(15) 0.7956(4) 0.0531(12) Uani 1 1 d . . .
H24A H 0.1054 0.4282 0.7927 0.064 Uiso 1 1 calc R . .
H24B H 0.0653 0.4116 0.7467 0.064 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Zn1 0.0345(3) 0.0356(3) 0.0288(3) 0.00321(17) -0.00212(17) -0.00154(17)
S1 0.0450(6) 0.0434(6) 0.0279(5) 0.0072(4) 0.0022(4) 0.0003(4)
S2 0.0325(5) 0.0344(5) 0.0354(5) 0.0064(4) 0.0010(4) -0.0003(4)
F1 0.082(2) 0.084(2) 0.096(3) 0.055(2) 0.014(2) -0.0125(19)
F2 0.075(2) 0.083(2) 0.101(3) 0.047(2) -0.030(2) 0.0070(18)
F3 0.081(2) 0.0460(17) 0.108(3) -0.0015(18) 0.015(2) 0.0055(15)
F4 0.074(2) 0.118(3) 0.0456(18) 0.0183(18) 0.0110(16) -0.009(2)
F5 0.072(2) 0.0473(17) 0.111(3) 0.0236(17) 0.0302(19) -0.0094(15)
F6 0.0462(16) 0.0621(18) 0.086(2) 0.0154(16) 0.0253(15) 0.0111(13)
O1 0.0407(16) 0.0493(17) 0.0342(15) 0.0129(13) -0.0024(12) -0.0053(13)
O2 0.0402(16) 0.0555(19) 0.0415(17) 0.0135(14) 0.0001(13) -0.0017(13)
O3 0.087(3) 0.075(2) 0.0326(17) -0.0053(16) 0.0022(17) 0.006(2)
O4 0.0480(16) 0.0311(14) 0.0323(14) 0.0037(11) 0.0005(12) -0.0032(12)
O5 0.0367(15) 0.0417(16) 0.0406(16) 0.0048(12) -0.0022(12) 0.0044(12)
O6 0.0405(16) 0.0395(16) 0.0460(17) -0.0002(13) -0.0097(13) -0.0019(13)
O7 0.0455(16) 0.0409(16) 0.0327(14) 0.0061(12) 0.0048(12) 0.0056(12)
N1 0.0372(17) 0.0356(17) 0.0320(17) 0.0071(14) -0.0007(14) -0.0015(14)
N2 0.0375(18) 0.0434(19) 0.0348(18) 0.0017(15) -0.0031(14) 0.0054(14)
C1 0.037(2) 0.043(2) 0.0264(19) 0.0033(16) -0.0030(16) -0.0104(17)
C2 0.063(3) 0.059(3) 0.028(2) 0.011(2) -0.009(2) -0.014(2)
C3 0.093(4) 0.075(4) 0.025(2) 0.003(2) -0.005(2) -0.025(3)
C4 0.085(4) 0.071(4) 0.045(3) -0.025(3) 0.002(3) -0.011(3)
C5 0.062(3) 0.051(3) 0.056(3) -0.013(2) -0.001(2) -0.002(2)
C6 0.050(3) 0.044(2) 0.037(2) 0.0010(18) -0.0041(19) -0.0072(19)
C7 0.099(4) 0.056(3) 0.035(2) 0.021(2) -0.023(3) -0.025(3)
C8 0.091(5) 0.056(4) 0.142(7) 0.012(4) -0.047(5) -0.003(3)
C9 0.149(8) 0.096(5) 0.078(5) 0.044(4) 0.005(5) -0.033(5)
C10 0.040(2) 0.045(2) 0.047(2) -0.0029(19) -0.0131(19) 0.0014(18)
C11 0.068(3) 0.042(3) 0.060(3) -0.002(2) -0.029(3) 0.005(2)
C12 0.057(4) 0.074(4) 0.105(5) -0.001(4) -0.040(4) 0.015(3)
C13 0.047(3) 0.103(5) 0.121(6) -0.013(5) -0.018(4) 0.022(3)
C14 0.038(3) 0.111(5) 0.107(5) 0.014(4) -0.008(3) -0.003(3)
C15 0.041(3) 0.081(4) 0.067(3) 0.004(3) -0.005(2) -0.003(2)
C16 0.073(4) 0.078(4) 0.073(4) 0.033(3) -0.042(3) -0.017(3)
C17 0.130(8) 0.133(8) 0.082(5) 0.029(5) -0.006(5) -0.012(6)
C18 0.084(8) 0.080(7) 0.086(9) 0.040(6) -0.010(7) -0.006(5)
C18' 0.073(10) 0.087(9) 0.062(9) 0.019(7) -0.006(7) 0.001(7)
C19 0.056(3) 0.057(3) 0.059(3) 0.025(3) 0.002(2) -0.006(2)
C20 0.046(2) 0.043(2) 0.054(3) 0.014(2) 0.010(2) -0.0014(19)
C21 0.060(3) 0.046(3) 0.041(2) 0.006(2) -0.001(2) 0.018(2)
C22 0.125(6) 0.095(5) 0.055(3) 0.019(3) 0.019(4) 0.072(4)
C23 0.127(6) 0.089(5) 0.057(4) 0.011(3) 0.037(4) 0.051(4)
C24 0.064(3) 0.058(3) 0.038(2) 0.014(2) 0.013(2) 0.010(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 O7 2.036(3) . ?
Zn1 N1 2.090(3) . ?
Zn1 N2 2.106(3) . ?
Zn1 O1 2.115(3) . ?
Zn1 O4 2.194(3) . ?
Zn1 O5 2.487(3) 9_567 ?
S1 O3 1.417(4) . ?
S1 O2 1.440(3) . ?
S1 O1 1.460(3) . ?
S1 C19 1.810(5) . ?
S2 O6 1.441(3) . ?
S2 O5 1.442(3) . ?
S2 O4 1.455(3) . ?
S2 C20 1.824(5) . ?
F1 C19 1.338(6) . ?
F2 C19 1.315(6) . ?
F3 C19 1.323(7) . ?
F4 C20 1.306(6) . ?
F5 C20 1.325(6) . ?
F6 C20 1.328(5) . ?
O5 Zn1 2.487(3) 9_567 ?
O7 C24 1.460(5) . ?
O7 C21 1.467(5) . ?
N1 C1 1.434(5) . ?
N1 H1A 0.9200 . ?
N1 H1B 0.9200 . ?
N2 C10 1.436(5) . ?
N2 H2A 0.9200 . ?
N2 H2B 0.9200 . ?
C1 C6 1.387(6) . ?
C1 C2 1.419(6) . ?
C2 C3 1.384(7) . ?
C2 C7 1.518(7) . ?
C3 C4 1.392(9) . ?
C3 H3A 0.9500 . ?
C4 C5 1.367(8) . ?
C4 H4A 0.9500 . ?
C5 C6 1.375(7) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.539(9) . ?
C7 C9 1.549(8) . ?
C7 H7A 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.402(6) . ?
C10 C15 1.411(7) . ?
C11 C12 1.412(8) . ?
C11 C16 1.477(9) . ?
C12 C13 1.370(11) . ?
C12 H12A 0.9500 . ?
C13 C14 1.351(10) . ?
C13 H13A 0.9500 . ?
C14 C15 1.372(8) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 C18' 1.537(12) . ?
C16 C17 1.546(11) . ?
C16 C18 1.563(11) . ?
C16 H16A 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18' H18D 0.9800 . ?
C18' H18E 0.9800 . ?
C18' H18F 0.9800 . ?
C21 C22 1.484(7) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.389(8) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.490(8) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

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
O7 Zn1 N1 101.82(13) . . ?
O7 Zn1 N2 101.06(13) . . ?
N1 Zn1 N2 157.06(14) . . ?
O7 Zn1 O1 94.16(12) . . ?
N1 Zn1 O1 89.67(12) . . ?
N2 Zn1 O1 87.17(13) . . ?
O7 Zn1 O4 89.35(11) . . ?
N1 Zn1 O4 89.86(12) . . ?
N2 Zn1 O4 91.91(12) . . ?
O1 Zn1 O4 176.48(12) . . ?
O7 Zn1 O5 172.24(11) . 9_567 ?
N1 Zn1 O5 82.62(12) . 9_567 ?
N2 Zn1 O5 74.81(12) . 9_567 ?
O1 Zn1 O5 92.21(11) . 9_567 ?
O4 Zn1 O5 84.27(10) . 9_567 ?
O3 S1 O2 117.1(2) . . ?
O3 S1 O1 113.9(2) . . ?
O2 S1 O1 112.99(18) . . ?
O3 S1 C19 104.8(3) . . ?
O2 S1 C19 105.0(2) . . ?
O1 S1 C19 100.9(2) . . ?
O6 S2 O5 115.03(18) . . ?
O6 S2 O4 114.10(17) . . ?
O5 S2 O4 113.93(18) . . ?
O6 S2 C20 104.9(2) . . ?
O5 S2 C20 104.5(2) . . ?
O4 S2 C20 102.6(2) . . ?
S1 O1 Zn1 130.35(19) . . ?
S2 O4 Zn1 135.26(17) . . ?
S2 O5 Zn1 135.70(18) . 9_567 ?
C24 O7 C21 109.7(3) . . ?
C24 O7 Zn1 125.6(3) . . ?
C21 O7 Zn1 124.4(2) . . ?
C1 N1 Zn1 118.0(3) . . ?
C1 N1 H1A 107.8 . . ?
Zn1 N1 H1A 107.8 . . ?
C1 N1 H1B 107.8 . . ?
Zn1 N1 H1B 107.8 . . ?
H1A N1 H1B 107.1 . . ?
C10 N2 Zn1 119.4(3) . . ?
C10 N2 H2A 107.5 . . ?
Zn1 N2 H2A 107.5 . . ?
C10 N2 H2B 107.5 . . ?
Zn1 N2 H2B 107.5 . . ?
H2A N2 H2B 107.0 . . ?
C6 C1 C2 120.1(4) . . ?
C6 C1 N1 118.5(4) . . ?
C2 C1 N1 121.3(4) . . ?
C3 C2 C1 117.2(5) . . ?
C3 C2 C7 121.7(4) . . ?
C1 C2 C7 121.1(4) . . ?
C2 C3 C4 121.9(5) . . ?
C2 C3 H3A 119.1 . . ?
C4 C3 H3A 119.1 . . ?
C5 C4 C3 120.0(5) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C4 C5 C6 119.8(5) . . ?
C4 C5 H5A 120.1 . . ?
C6 C5 H5A 120.1 . . ?
C5 C6 C1 121.0(4) . . ?
C5 C6 H6A 119.5 . . ?
C1 C6 H6A 119.5 . . ?
C2 C7 C8 111.4(4) . . ?
C2 C7 C9 112.0(6) . . ?
C8 C7 C9 113.6(6) . . ?
C2 C7 H7A 106.4 . . ?
C8 C7 H7A 106.4 . . ?
C9 C7 H7A 106.4 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 121.0(5) . . ?
C11 C10 N2 122.2(5) . . ?
C15 C10 N2 116.8(4) . . ?
C10 C11 C12 115.7(6) . . ?
C10 C11 C16 122.9(5) . . ?
C12 C11 C16 121.4(5) . . ?
C13 C12 C11 121.9(6) . . ?
C13 C12 H12A 119.1 . . ?
C11 C12 H12A 119.1 . . ?
C14 C13 C12 121.7(6) . . ?
C14 C13 H13A 119.1 . . ?
C12 C13 H13A 119.1 . . ?
C13 C14 C15 119.2(7) . . ?
C13 C14 H14A 120.4 . . ?
C15 C14 H14A 120.4 . . ?
C14 C15 C10 120.4(6) . . ?
C14 C15 H15A 119.8 . . ?
C10 C15 H15A 119.8 . . ?
C11 C16 C18' 131.0(15) . . ?
C11 C16 C17 109.7(5) . . ?
C18' C16 C17 96.9(14) . . ?
C11 C16 C18 106.2(11) . . ?
C18' C16 C18 26.1(8) . . ?
C17 C16 C18 117.9(10) . . ?
C11 C16 H16A 107.5 . . ?
C18' C16 H16A 102.3 . . ?
C17 C16 H16A 107.5 . . ?
C18 C16 H16A 107.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
C16 C18' H18D 109.5 . . ?
C16 C18' H18E 109.5 . . ?
H18D C18' H18E 109.5 . . ?
C16 C18' H18F 109.5 . . ?
H18D C18' H18F 109.5 . . ?
H18E C18' H18F 109.5 . . ?
F2 C19 F3 109.1(5) . . ?
F2 C19 F1 107.7(4) . . ?
F3 C19 F1 108.0(5) . . ?
F2 C19 S1 111.3(4) . . ?
F3 C19 S1 110.8(3) . . ?
F1 C19 S1 109.9(4) . . ?
F4 C20 F5 109.2(4) . . ?
F4 C20 F6 108.3(4) . . ?
F5 C20 F6 107.7(4) . . ?
F4 C20 S2 111.2(3) . . ?
F5 C20 S2 110.0(4) . . ?
F6 C20 S2 110.3(3) . . ?
O7 C21 C22 104.3(4) . . ?
O7 C21 H21A 110.9 . . ?
C22 C21 H21A 110.9 . . ?
O7 C21 H21B 110.9 . . ?
C22 C21 H21B 110.9 . . ?
H21A C21 H21B 108.9 . . ?
C23 C22 C21 109.3(5) . . ?
C23 C22 H22A 109.8 . . ?
C21 C22 H22A 109.8 . . ?
C23 C22 H22B 109.8 . . ?
C21 C22 H22B 109.8 . . ?
H22A C22 H22B 108.3 . . ?
C22 C23 C24 107.7(5) . . ?
C22 C23 H23A 110.2 . . ?
C24 C23 H23A 110.2 . . ?
C22 C23 H23B 110.2 . . ?
C24 C23 H23B 110.2 . . ?
H23A C23 H23B 108.5 . . ?
O7 C24 C23 104.3(4) . . ?
O7 C24 H24A 110.9 . . ?
C23 C24 H24A 110.9 . . ?
O7 C24 H24B 110.9 . . ?
C23 C24 H24B 110.9 . . ?
H24A C24 H24B 108.9 . . ?

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
O3 S1 O1 Zn1 -85.5(3) . . . . ?
O2 S1 O1 Zn1 51.3(3) . . . . ?
C19 S1 O1 Zn1 162.8(3) . . . . ?
O7 Zn1 O1 S1 -154.7(2) . . . . ?
N1 Zn1 O1 S1 -52.9(3) . . . . ?
N2 Zn1 O1 S1 104.4(3) . . . . ?
O4 Zn1 O1 S1 29(2) . . . . ?
O5 Zn1 O1 S1 29.7(2) 9_567 . . . ?
O6 S2 O4 Zn1 30.2(3) . . . . ?
O5 S2 O4 Zn1 -104.7(3) . . . . ?
C20 S2 O4 Zn1 143.0(3) . . . . ?
O7 Zn1 O4 S2 -134.3(3) . . . . ?
N1 Zn1 O4 S2 123.9(3) . . . . ?
N2 Zn1 O4 S2 -33.3(3) . . . . ?
O1 Zn1 O4 S2 42(2) . . . . ?
O5 Zn1 O4 S2 41.3(2) 9_567 . . . ?
O6 S2 O5 Zn1 -15.7(3) . . . 9_567 ?
O4 S2 O5 Zn1 118.7(2) . . . 9_567 ?
C20 S2 O5 Zn1 -130.1(3) . . . 9_567 ?
N1 Zn1 O7 C24 70.7(4) . . . . ?
N2 Zn1 O7 C24 -110.8(4) . . . . ?
O1 Zn1 O7 C24 161.2(4) . . . . ?
O4 Zn1 O7 C24 -19.0(4) . . . . ?
O5 Zn1 O7 C24 -53.6(10) 9_567 . . . ?
N1 Zn1 O7 C21 -102.3(3) . . . . ?
N2 Zn1 O7 C21 76.2(4) . . . . ?
O1 Zn1 O7 C21 -11.7(3) . . . . ?
O4 Zn1 O7 C21 168.0(3) . . . . ?
O5 Zn1 O7 C21 133.4(7) 9_567 . . . ?
O7 Zn1 N1 C1 -3.7(3) . . . . ?
N2 Zn1 N1 C1 -179.8(3) . . . . ?
O1 Zn1 N1 C1 -97.8(3) . . . . ?
O4 Zn1 N1 C1 85.7(3) . . . . ?
O5 Zn1 N1 C1 169.9(3) 9_567 . . . ?
O7 Zn1 N2 C10 -7.1(3) . . . . ?
N1 Zn1 N2 C10 169.0(3) . . . . ?
O1 Zn1 N2 C10 86.6(3) . . . . ?
O4 Zn1 N2 C10 -96.8(3) . . . . ?
O5 Zn1 N2 C10 179.6(3) 9_567 . . . ?
Zn1 N1 C1 C6 76.7(4) . . . . ?
Zn1 N1 C1 C2 -101.6(4) . . . . ?
C6 C1 C2 C3 -0.5(7) . . . . ?
N1 C1 C2 C3 177.9(4) . . . . ?
C6 C1 C2 C7 177.6(4) . . . . ?
N1 C1 C2 C7 -4.1(7) . . . . ?
C1 C2 C3 C4 0.4(8) . . . . ?
C7 C2 C3 C4 -177.6(5) . . . . ?
C2 C3 C4 C5 0.0(9) . . . . ?
C3 C4 C5 C6 -0.5(9) . . . . ?
C4 C5 C6 C1 0.5(8) . . . . ?
C2 C1 C6 C5 0.0(7) . . . . ?
N1 C1 C6 C5 -178.4(4) . . . . ?
C3 C2 C7 C8 86.8(7) . . . . ?
C1 C2 C7 C8 -91.2(6) . . . . ?
C3 C2 C7 C9 -41.7(8) . . . . ?
C1 C2 C7 C9 140.3(5) . . . . ?
Zn1 N2 C10 C11 -103.2(4) . . . . ?
Zn1 N2 C10 C15 77.9(5) . . . . ?
C15 C10 C11 C12 -2.0(7) . . . . ?
N2 C10 C11 C12 179.1(5) . . . . ?
C15 C10 C11 C16 177.4(5) . . . . ?
N2 C10 C11 C16 -1.5(8) . . . . ?
C10 C11 C12 C13 2.3(9) . . . . ?
C16 C11 C12 C13 -177.2(7) . . . . ?
C11 C12 C13 C14 -3.1(12) . . . . ?
C12 C13 C14 C15 3.4(12) . . . . ?
C13 C14 C15 C10 -3.1(11) . . . . ?
C11 C10 C15 C14 2.5(9) . . . . ?
N2 C10 C15 C14 -178.5(6) . . . . ?
C10 C11 C16 C18' 156.0(13) . . . . ?
C12 C11 C16 C18' -24.6(15) . . . . ?
C10 C11 C16 C17 -85.4(7) . . . . ?
C12 C11 C16 C17 94.0(7) . . . . ?
C10 C11 C16 C18 146.2(8) . . . . ?
C12 C11 C16 C18 -34.4(9) . . . . ?
O3 S1 C19 F2 -52.0(5) . . . . ?
O2 S1 C19 F2 -176.0(4) . . . . ?
O1 S1 C19 F2 66.5(4) . . . . ?
O3 S1 C19 F3 -173.6(4) . . . . ?
O2 S1 C19 F3 62.5(4) . . . . ?
O1 S1 C19 F3 -55.1(4) . . . . ?
O3 S1 C19 F1 67.1(5) . . . . ?
O2 S1 C19 F1 -56.8(4) . . . . ?
O1 S1 C19 F1 -174.4(4) . . . . ?
O6 S2 C20 F4 -174.5(3) . . . . ?
O5 S2 C20 F4 -53.1(4) . . . . ?
O4 S2 C20 F4 66.0(4) . . . . ?
O6 S2 C20 F5 -53.3(4) . . . . ?
O5 S2 C20 F5 68.1(4) . . . . ?
O4 S2 C20 F5 -172.8(3) . . . . ?
O6 S2 C20 F6 65.3(4) . . . . ?
O5 S2 C20 F6 -173.3(3) . . . . ?
O4 S2 C20 F6 -54.1(4) . . . . ?
C24 O7 C21 C22 -0.8(6) . . . . ?
Zn1 O7 C21 C22 173.1(4) . . . . ?
O7 C21 C22 C23 -13.1(9) . . . . ?
C21 C22 C23 C24 21.8(10) . . . . ?
C21 O7 C24 C23 13.1(6) . . . . ?
Zn1 O7 C24 C23 -160.7(4) . . . . ?
C22 C23 C24 O7 -21.4(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.649
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.186

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.250 0.000 0.491 560 274 ' '
2 0.250 0.500 0.509 560 276 ' '
3 0.750 0.000 0.009 560 276 ' '
4 0.750 0.500 0.991 560 274 ' '