# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_frit14

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H30 N4 O2 Zn'
_chemical_formula_weight         543.95

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   12.3863(9)
_cell_length_b                   11.7173(8)
_cell_length_c                   17.9207(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.189(3)
_cell_angle_gamma                90.00
_cell_volume                     2590.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4928
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      25.09

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7636
_exptl_absorpt_correction_T_max  0.8911
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            19876
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1360
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         32.10
_reflns_number_total             7734
_reflns_number_gt                5345
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0700P)²+2.2000P] where P=(Fo²+2Fc²)/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         7734
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1394
_refine_ls_wR_factor_gt          0.1303
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002

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 0.32034(2) 0.24979(2) 0.854484(14) 0.01199(9) Uani 1 1 d . . .
O1 O 0.15324(13) 0.23139(13) 0.85397(9) 0.0153(3) Uiso 1 1 d . . .
O2 O 0.35443(14) 0.26401(13) 0.74383(9) 0.0159(3) Uani 1 1 d . . .
N1 N 0.32582(14) 0.07453(17) 0.85410(10) 0.0121(4) Uani 1 1 d . . .
N2 N 0.50638(15) 0.20061(17) 0.87221(10) 0.0131(4) Uani 1 1 d . . .
N3 N 0.31386(15) 0.42542(17) 0.85556(10) 0.0125(4) Uani 1 1 d . . .
N4 N 0.31438(15) 0.29806(17) 0.97961(11) 0.0132(4) Uani 1 1 d . . .
C1 C 0.0045(2) 0.1793(2) 0.92077(17) 0.0279(6) Uani 1 1 d . . .
H1A H -0.0214 0.2533 0.9009 0.042 Uiso 1 1 calc R . .
H1B H 0.0089 0.1809 0.9756 0.042 Uiso 1 1 calc R . .
H1C H -0.0460 0.1192 0.9021 0.042 Uiso 1 1 calc R . .
C2 C 0.11579(19) 0.1551(2) 0.89555(13) 0.0158(5) Uani 1 1 d . . .
C3 C 0.16577(19) 0.0535(2) 0.91785(13) 0.0151(5) Uani 1 1 d . . .
H3A H 0.1317 0.0087 0.9532 0.018 Uiso 1 1 calc R . .
C4 C 0.26324(18) 0.0102(2) 0.89281(13) 0.0136(4) Uani 1 1 d . . .
C5 C 0.29299(19) -0.1110(2) 0.91529(14) 0.0182(5) Uani 1 1 d . . .
H5A H 0.3608 -0.1321 0.8947 0.027 Uiso 1 1 calc R . .
H5B H 0.2351 -0.1628 0.8957 0.027 Uiso 1 1 calc R . .
H5C H 0.3023 -0.1166 0.9701 0.027 Uiso 1 1 calc R . .
C6 C 0.51315(18) 0.10118(19) 0.83234(12) 0.0127(4) Uani 1 1 d . . .
C7 C 0.41708(18) 0.0324(2) 0.82233(12) 0.0132(4) Uani 1 1 d . . .
C8 C 0.41862(19) -0.0636(2) 0.77778(13) 0.0155(5) Uani 1 1 d . . .
H8A H 0.3546 -0.1079 0.7682 0.019 Uiso 1 1 calc R . .
C9 C 0.5144(2) -0.0967(2) 0.74625(13) 0.0169(5) Uani 1 1 d . . .
H9A H 0.5135 -0.1631 0.7157 0.020 Uiso 1 1 calc R . .
C10 C 0.6081(2) -0.0354(2) 0.75873(13) 0.0178(5) Uani 1 1 d . . .
H10A H 0.6722 -0.0606 0.7384 0.021 Uiso 1 1 calc R . .
C11 C 0.60954(19) 0.0660(2) 0.80216(13) 0.0155(5) Uani 1 1 d . . .
C12 C 0.70200(19) 0.1359(2) 0.81798(14) 0.0192(5) Uani 1 1 d . . .
H12A H 0.7688 0.1155 0.7994 0.023 Uiso 1 1 calc R . .
C13 C 0.6953(2) 0.2324(2) 0.85987(15) 0.0196(5) Uani 1 1 d . . .
H13A H 0.7577 0.2784 0.8714 0.024 Uiso 1 1 calc R . .
C14 C 0.59451(19) 0.2642(2) 0.88622(13) 0.0154(5) Uani 1 1 d . . .
C15 C 0.5858(2) 0.3713(2) 0.93086(14) 0.0206(5) Uani 1 1 d . . .
H15A H 0.5114 0.3796 0.9446 0.031 Uiso 1 1 calc R . .
H15B H 0.6044 0.4370 0.9008 0.031 Uiso 1 1 calc R . .
H15C H 0.6358 0.3672 0.9764 0.031 Uiso 1 1 calc R . .
C16 C 0.4891(2) 0.3135(2) 0.66343(15) 0.0236(5) Uani 1 1 d . . .
H16A H 0.4720 0.2361 0.6454 0.035 Uiso 1 1 calc R . .
H16B H 0.5660 0.3180 0.6816 0.035 Uiso 1 1 calc R . .
H16C H 0.4736 0.3680 0.6223 0.035 Uiso 1 1 calc R . .
C17 C 0.42063(19) 0.3421(2) 0.72662(13) 0.0158(5) Uani 1 1 d . . .
C18 C 0.43297(19) 0.4490(2) 0.75941(13) 0.0163(5) Uani 1 1 d . . .
H18A H 0.4851 0.4981 0.7406 0.020 Uiso 1 1 calc R . .
C19 C 0.37561(19) 0.49232(19) 0.81819(12) 0.0143(5) Uani 1 1 d . . .
C20 C 0.3931(2) 0.6176(2) 0.83594(14) 0.0216(5) Uani 1 1 d . . .
H20A H 0.3501 0.6394 0.8770 0.032 Uiso 1 1 calc R . .
H20B H 0.3704 0.6632 0.7914 0.032 Uiso 1 1 calc R . .
H20C H 0.4701 0.6313 0.8509 0.032 Uiso 1 1 calc R . .
C21 C 0.25389(18) 0.39641(19) 0.97792(12) 0.0125(4) Uani 1 1 d . . .
C22 C 0.25228(18) 0.46581(19) 0.91206(13) 0.0131(4) Uani 1 1 d . . .
C23 C 0.18573(19) 0.5605(2) 0.90678(13) 0.0164(5) Uani 1 1 d . . .
H23A H 0.1803 0.6049 0.8622 0.020 Uiso 1 1 calc R . .
C24 C 0.12573(19) 0.5922(2) 0.96674(13) 0.0179(5) Uani 1 1 d . . .
H24A H 0.0807 0.6579 0.9620 0.021 Uiso 1 1 calc R . .
C25 C 0.13107(19) 0.5298(2) 1.03193(14) 0.0167(5) Uani 1 1 d . . .
H25A H 0.0917 0.5535 1.0723 0.020 Uiso 1 1 calc R . .
C26 C 0.19552(18) 0.4301(2) 1.03855(13) 0.0150(5) Uani 1 1 d . . .
C27 C 0.2064(2) 0.3614(2) 1.10351(13) 0.0175(5) Uani 1 1 d . . .
H27A H 0.1691 0.3811 1.1457 0.021 Uiso 1 1 calc R . .
C28 C 0.2705(2) 0.2667(2) 1.10561(14) 0.0188(5) Uani 1 1 d . . .
H28A H 0.2798 0.2216 1.1498 0.023 Uiso 1 1 calc R . .
C29 C 0.32339(19) 0.23572(19) 1.04131(13) 0.0142(5) Uani 1 1 d . . .
C30 C 0.3914(2) 0.1293(2) 1.04299(14) 0.0192(5) Uani 1 1 d . . .
H30A H 0.4221 0.1202 0.9948 0.029 Uiso 1 1 calc R . .
H30B H 0.3461 0.0630 1.0520 0.029 Uiso 1 1 calc R . .
H30C H 0.4502 0.1352 1.0832 0.029 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 N1 2.055(2) . ?
Zn1 N3 2.060(2) . ?
Zn1 O2 2.0711(17) . ?
Zn1 O1 2.0802(17) . ?
Zn1 N4 2.3203(19) . ?
Zn1 N2 2.3686(19) . ?
O1 C2 1.278(3) . ?
O2 C17 1.285(3) . ?
N1 C4 1.322(3) . ?
N1 C7 1.401(3) . ?
N2 C14 1.327(3) . ?
N2 C6 1.373(3) . ?
N3 C19 1.319(3) . ?
N3 C22 1.404(3) . ?
N4 C29 1.321(3) . ?
N4 C21 1.373(3) . ?
C1 C2 1.516(3) . ?
C2 C3 1.384(3) . ?
C3 C4 1.419(3) . ?
C4 C5 1.513(3) . ?
C6 C11 1.416(3) . ?
C6 C7 1.435(3) . ?
C7 C8 1.381(3) . ?
C8 C9 1.413(3) . ?
C9 C10 1.367(3) . ?
C10 C11 1.420(3) . ?
C11 C12 1.415(3) . ?
C12 C13 1.364(4) . ?
C13 C14 1.423(3) . ?
C14 C15 1.497(3) . ?
C16 C17 1.512(3) . ?
C17 C18 1.386(3) . ?
C18 C19 1.417(3) . ?
C19 C20 1.513(3) . ?
C21 C26 1.415(3) . ?
C21 C22 1.432(3) . ?
C22 C23 1.381(3) . ?
C23 C24 1.410(3) . ?
C24 C25 1.375(3) . ?
C25 C26 1.414(3) . ?
C26 C27 1.412(3) . ?
C27 C28 1.363(3) . ?
C28 C29 1.423(3) . ?
C29 C30 1.504(3) . ?

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
N1 Zn1 N3 179.49(8) . . ?
N1 Zn1 O2 93.87(7) . . ?
N3 Zn1 O2 86.57(7) . . ?
N1 Zn1 O1 85.96(7) . . ?
N3 Zn1 O1 93.67(7) . . ?
O2 Zn1 O1 107.04(7) . . ?
N1 Zn1 N4 104.53(7) . . ?
N3 Zn1 N4 75.09(7) . . ?
O2 Zn1 N4 158.87(7) . . ?
O1 Zn1 N4 84.89(7) . . ?
N1 Zn1 N2 74.05(7) . . ?
N3 Zn1 N2 106.27(7) . . ?
O2 Zn1 N2 82.41(7) . . ?
O1 Zn1 N2 158.57(7) . . ?
N4 Zn1 N2 92.60(7) . . ?
C2 O1 Zn1 118.92(15) . . ?
C17 O2 Zn1 118.48(15) . . ?
C4 N1 C7 123.0(2) . . ?
C4 N1 Zn1 123.16(15) . . ?
C7 N1 Zn1 112.44(15) . . ?
C14 N2 C6 119.1(2) . . ?
C14 N2 Zn1 131.50(16) . . ?
C6 N2 Zn1 103.95(14) . . ?
C19 N3 C22 122.9(2) . . ?
C19 N3 Zn1 124.33(16) . . ?
C22 N3 Zn1 111.58(14) . . ?
C29 N4 C21 119.1(2) . . ?
C29 N4 Zn1 131.78(16) . . ?
C21 N4 Zn1 104.37(14) . . ?
O1 C2 C3 126.4(2) . . ?
O1 C2 C1 115.5(2) . . ?
C3 C2 C1 118.0(2) . . ?
C2 C3 C4 126.0(2) . . ?
N1 C4 C3 121.2(2) . . ?
N1 C4 C5 122.3(2) . . ?
C3 C4 C5 116.4(2) . . ?
N2 C6 C11 122.6(2) . . ?
N2 C6 C7 116.9(2) . . ?
C11 C6 C7 120.5(2) . . ?
C8 C7 N1 125.2(2) . . ?
C8 C7 C6 118.4(2) . . ?
N1 C7 C6 116.2(2) . . ?
C7 C8 C9 120.7(2) . . ?
C10 C9 C8 121.4(2) . . ?
C9 C10 C11 119.9(2) . . ?
C12 C11 C6 116.8(2) . . ?
C12 C11 C10 124.3(2) . . ?
C6 C11 C10 118.9(2) . . ?
C13 C12 C11 120.1(2) . . ?
C12 C13 C14 119.9(2) . . ?
N2 C14 C13 121.4(2) . . ?
N2 C14 C15 118.3(2) . . ?
C13 C14 C15 120.3(2) . . ?
O2 C17 C18 126.2(2) . . ?
O2 C17 C16 115.8(2) . . ?
C18 C17 C16 118.0(2) . . ?
C17 C18 C19 126.6(2) . . ?
N3 C19 C18 121.1(2) . . ?
N3 C19 C20 123.2(2) . . ?
C18 C19 C20 115.6(2) . . ?
N4 C21 C26 122.2(2) . . ?
N4 C21 C22 117.5(2) . . ?
C26 C21 C22 120.3(2) . . ?
C23 C22 N3 125.6(2) . . ?
C23 C22 C21 118.5(2) . . ?
N3 C22 C21 115.8(2) . . ?
C22 C23 C24 120.8(2) . . ?
C25 C24 C23 121.3(2) . . ?
C24 C25 C26 119.6(2) . . ?
C25 C26 C27 123.5(2) . . ?
C25 C26 C21 119.3(2) . . ?
C27 C26 C21 117.2(2) . . ?
C28 C27 C26 119.9(2) . . ?
C27 C28 C29 119.7(2) . . ?
N4 C29 C28 121.8(2) . . ?
N4 C29 C30 118.7(2) . . ?
C28 C29 C30 119.5(2) . . ?

_diffrn_measured_fraction_theta_max 0.853
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.698
_refine_diff_density_min         -0.692
_refine_diff_density_rms         0.094
_database_code_depnum_ccdc_archive 'CCDC 1005746'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_pep311m-squ

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C50 H38 N4 O2 Zn, 4(C H2 Cl2)'
_chemical_formula_sum            'C54 H46 Cl8 N4 O2 Zn'
_chemical_formula_weight         1131.92

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

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'
'-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                   18.4261(19)
_cell_length_b                   18.3114(19)
_cell_length_c                   17.7719(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.9120(10)
_cell_angle_gamma                90.00
_cell_volume                     5766.6(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      3.74
_cell_measurement_theta_max      30.22

_exptl_crystal_description       block
_exptl_crystal_colour            orange-red
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2320
_exptl_absorpt_coefficient_mu    0.838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7018
_exptl_absorpt_correction_T_max  0.7872
_exptl_absorpt_process_details   'Sadabs (Bruker)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            38222
_diffrn_reflns_av_R_equivalents  0.1026
_diffrn_reflns_av_sigmaI/netI    0.0663
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.62
_diffrn_reflns_theta_max         30.57
_reflns_number_total             8315
_reflns_number_gt                6383
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          SQUEEZE

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0698P)²+0.0000P] where P=(Fo²+2Fc²)/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         8315
_refine_ls_number_parameters     349
_refine_ls_number_restraints     120
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1294
_refine_ls_wR_factor_gt          0.1246
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.010
_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
C26 C 0.39171(14) 0.79759(13) 0.70259(15) 0.0392(6) Uani 1 1 d . . .
H26A H 0.3836 0.7520 0.6715 0.047 Uiso 1 1 calc R . .
H26B H 0.4300 0.7876 0.7527 0.047 Uiso 1 1 calc R . .
Cl1 Cl 0.30685(3) 0.82321(3) 0.72173(3) 0.03295(13) Uani 1 1 d . . .
Cl2 Cl 0.42624(3) 0.86609(3) 0.65095(3) 0.03820(15) Uani 1 1 d . . .
Cl3 Cl 0.17865(5) 0.12871(4) 0.32632(4) 0.0618(2) Uani 1 1 d DU . .
Cl4 Cl 0.2743(3) 0.1524(2) 0.4813(2) 0.0641(11) Uani 0.34 1 d PDU A 1
C27 C 0.2673(10) 0.1124(15) 0.3914(9) 0.070(5) Uani 0.34 1 d PDU A 1
H27A H 0.2755 0.0591 0.3983 0.084 Uiso 0.34 1 calc PR A 1
H27B H 0.3071 0.1323 0.3694 0.084 Uiso 0.34 1 calc PR A 1
Cl4A Cl 0.24348(17) 0.1960(2) 0.47602(13) 0.0686(8) Uani 0.34 1 d PDU . 2
C27A C 0.2522(6) 0.1334(7) 0.4076(6) 0.055(3) Uani 0.34 1 d PDU A 2
H27C H 0.2983 0.1450 0.3916 0.066 Uiso 0.34 1 calc PR A 2
H27D H 0.2595 0.0845 0.4325 0.066 Uiso 0.34 1 calc PR A 2
Cl4B Cl 0.2978(4) 0.1205(3) 0.4861(3) 0.0893(18) Uani 0.32 1 d PDU A 3
C27B C 0.2684(8) 0.0962(11) 0.3879(6) 0.043(3) Uani 0.32 1 d PDU A 3
H27E H 0.2673 0.0422 0.3854 0.052 Uiso 0.32 1 calc PR A 3
H27F H 0.3080 0.1125 0.3636 0.052 Uiso 0.32 1 calc PR A 3
Zn1 Zn 0.0000 0.105506(15) 0.7500 0.01486(9) Uani 1 2 d S . .
O1 O 0.01484(7) 0.18194(7) 0.84078(7) 0.0180(3) Uani 1 1 d . . .
N1 N 0.11573(9) 0.11634(8) 0.75824(8) 0.0155(3) Uani 1 1 d . . .
N2 N 0.05417(8) 0.02676(8) 0.84374(8) 0.0171(3) Uani 1 1 d . . .
C1 C 0.16033(10) 0.09869(9) 0.83385(9) 0.0164(3) Uani 1 1 d . . .
C2 C 0.23007(10) 0.12880(10) 0.87086(10) 0.0198(4) Uani 1 1 d . . .
H2 H 0.2523 0.1626 0.8433 0.024 Uiso 1 1 calc R . .
C3 C 0.26870(11) 0.11031(11) 0.94848(11) 0.0237(4) Uani 1 1 d . . .
H3 H 0.3163 0.1320 0.9723 0.028 Uiso 1 1 calc R . .
C4 C 0.23865(11) 0.06144(11) 0.99015(10) 0.0243(4) Uani 1 1 d . . .
H4 H 0.2659 0.0483 1.0419 0.029 Uiso 1 1 calc R . .
C5 C 0.16667(11) 0.03077(10) 0.95559(10) 0.0211(4) Uani 1 1 d . . .
C6 C 0.12618(10) 0.05117(10) 0.87833(10) 0.0178(3) Uani 1 1 d . . .
C7 C 0.13135(12) -0.02036(11) 0.99426(11) 0.0263(4) Uani 1 1 d . . .
H7 H 0.1567 -0.0364 1.0456 0.032 Uiso 1 1 calc R . .
C8 C 0.06146(12) -0.04639(11) 0.95805(11) 0.0261(4) Uani 1 1 d . . .
H8 H 0.0383 -0.0814 0.9834 0.031 Uiso 1 1 calc R . .
C9 C 0.02307(11) -0.02092(10) 0.88196(10) 0.0210(4) Uani 1 1 d . . .
C10 C -0.05438(12) -0.04905(11) 0.84234(12) 0.0282(4) Uani 1 1 d . . .
H10A H -0.0700 -0.0314 0.7882 0.042 Uiso 1 1 calc R . .
H10B H -0.0900 -0.0316 0.8703 0.042 Uiso 1 1 calc R . .
H10C H -0.0538 -0.1026 0.8426 0.042 Uiso 1 1 calc R . .
C11 C -0.02589(10) 0.18602(9) 0.88812(9) 0.0160(3) Uani 1 1 d . . .
C12 C 0.01288(10) 0.21458(10) 0.96835(10) 0.0186(3) Uani 1 1 d . . .
C13 C 0.09060(11) 0.20508(10) 0.99627(11) 0.0222(4) Uani 1 1 d . . .
H13 H 0.1175 0.1831 0.9636 0.027 Uiso 1 1 calc R . .
C14 C 0.12933(12) 0.22714(12) 1.07090(11) 0.0292(4) Uani 1 1 d . . .
H14 H 0.1823 0.2196 1.0893 0.035 Uiso 1 1 calc R . .
C15 C 0.09114(13) 0.26017(14) 1.11901(12) 0.0392(6) Uani 1 1 d . . .
H15 H 0.1177 0.2755 1.1702 0.047 Uiso 1 1 calc R . .
C16 C 0.01423(14) 0.27057(16) 1.09189(14) 0.0467(7) Uani 1 1 d . . .
H16 H -0.0121 0.2935 1.1246 0.056 Uiso 1 1 calc R . .
C17 C -0.02532(12) 0.24774(13) 1.01704(12) 0.0346(5) Uani 1 1 d . . .
H17 H -0.0784 0.2548 0.9992 0.042 Uiso 1 1 calc R . .
C18 C 0.14479(10) 0.13300(9) 0.69950(9) 0.0155(3) Uani 1 1 d . . .
C19 C 0.22493(10) 0.11579(10) 0.70106(9) 0.0177(3) Uani 1 1 d . . .
C20 C 0.25390(11) 0.04516(11) 0.71850(11) 0.0241(4) Uani 1 1 d . . .
H20 H 0.2242 0.0084 0.7335 0.029 Uiso 1 1 calc R . .
C21 C 0.32632(13) 0.02911(13) 0.71379(13) 0.0337(5) Uani 1 1 d . . .
H21 H 0.3456 -0.0190 0.7246 0.040 Uiso 1 1 calc R . .
C22 C 0.37079(13) 0.08303(15) 0.69330(13) 0.0376(5) Uani 1 1 d . . .
H22 H 0.4204 0.0717 0.6907 0.045 Uiso 1 1 calc R . .
C23 C 0.34272(12) 0.15294(13) 0.67680(12) 0.0319(5) Uani 1 1 d . . .
H23 H 0.3731 0.1899 0.6633 0.038 Uiso 1 1 calc R . .
C24 C 0.26982(11) 0.16918(11) 0.68003(10) 0.0233(4) Uani 1 1 d . . .
H24 H 0.2504 0.2171 0.6678 0.028 Uiso 1 1 calc R . .
C25 C 0.10134(10) 0.16351(10) 0.62864(9) 0.0177(3) Uani 1 1 d . . .
H25 H 0.1256 0.1694 0.5882 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
C26 Cl1 1.753(2) . ?
C26 Cl2 1.772(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
Cl3 C27A 1.690(10) . ?
Cl3 C27 1.750(13) . ?
Cl3 C27B 1.815(10) . ?
Cl4 C27 1.730(12) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
Cl4A C27A 1.712(9) . ?
C27A H27C 0.9900 . ?
C27A H27D 0.9900 . ?
Cl4B C27B 1.737(9) . ?
C27B H27E 0.9900 . ?
C27B H27F 0.9900 . ?
Zn1 O1 2.0963(12) . ?
Zn1 O1 2.0963(12) 2_556 ?
Zn1 N1 2.1063(15) . ?
Zn1 N1 2.1063(15) 2_556 ?
Zn1 N2 2.2225(14) 2_556 ?
Zn1 N2 2.2225(14) . ?
O1 C11 1.2741(19) . ?
N1 C18 1.333(2) . ?
N1 C1 1.407(2) . ?
N2 C9 1.329(2) . ?
N2 C6 1.375(2) . ?
C1 C2 1.387(2) . ?
C1 C6 1.432(2) . ?
C2 C3 1.409(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.371(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.416(3) . ?
C4 H4 0.9500 . ?
C5 C7 1.420(3) . ?
C5 C6 1.421(2) . ?
C7 C8 1.358(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.422(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.499(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C25 1.402(2) 2_556 ?
C11 C12 1.503(2) . ?
C12 C13 1.392(3) . ?
C12 C17 1.395(3) . ?
C13 C14 1.383(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.394(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C25 1.409(2) . ?
C18 C19 1.503(2) . ?
C19 C24 1.396(3) . ?
C19 C20 1.401(3) . ?
C20 C21 1.391(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.394(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.382(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.392(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C11 1.402(2) 2_556 ?
C25 H25 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
Cl1 C26 Cl2 112.15(12) . . ?
Cl1 C26 H26A 109.2 . . ?
Cl2 C26 H26A 109.2 . . ?
Cl1 C26 H26B 109.2 . . ?
Cl2 C26 H26B 109.2 . . ?
H26A C26 H26B 107.9 . . ?
Cl4 C27 Cl3 111.0(9) . . ?
Cl4 C27 H27A 109.4 . . ?
Cl3 C27 H27A 109.4 . . ?
Cl4 C27 H27B 109.4 . . ?
Cl3 C27 H27B 109.4 . . ?
H27A C27 H27B 108.0 . . ?
Cl3 C27A Cl4A 115.5(6) . . ?
Cl3 C27A H27C 108.4 . . ?
Cl4A C27A H27C 108.4 . . ?
Cl3 C27A H27D 108.4 . . ?
Cl4A C27A H27D 108.4 . . ?
H27C C27A H27D 107.5 . . ?
Cl4B C27B Cl3 120.2(8) . . ?
Cl4B C27B H27E 107.3 . . ?
Cl3 C27B H27E 107.3 . . ?
Cl4B C27B H27F 107.3 . . ?
Cl3 C27B H27F 107.3 . . ?
H27E C27B H27F 106.9 . . ?
O1 Zn1 O1 96.23(7) . 2_556 ?
O1 Zn1 N1 88.14(5) . . ?
O1 Zn1 N1 84.65(5) 2_556 . ?
O1 Zn1 N1 84.65(5) . 2_556 ?
O1 Zn1 N1 88.14(5) 2_556 2_556 ?
N1 Zn1 N1 169.20(8) . 2_556 ?
O1 Zn1 N2 161.28(5) . 2_556 ?
O1 Zn1 N2 85.37(5) 2_556 2_556 ?
N1 Zn1 N2 110.57(5) . 2_556 ?
N1 Zn1 N2 76.76(5) 2_556 2_556 ?
O1 Zn1 N2 85.37(5) . . ?
O1 Zn1 N2 161.28(5) 2_556 . ?
N1 Zn1 N2 76.76(5) . . ?
N1 Zn1 N2 110.57(5) 2_556 . ?
N2 Zn1 N2 99.09(8) 2_556 . ?
C11 O1 Zn1 124.84(11) . . ?
C18 N1 C1 123.07(15) . . ?
C18 N1 Zn1 125.71(12) . . ?
C1 N1 Zn1 111.10(11) . . ?
C9 N2 C6 118.92(15) . . ?
C9 N2 Zn1 129.91(12) . . ?
C6 N2 Zn1 107.71(11) . . ?
C2 C1 N1 125.74(16) . . ?
C2 C1 C6 118.03(15) . . ?
N1 C1 C6 115.89(15) . . ?
C1 C2 C3 121.49(17) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 121.00(18) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.56(16) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C7 123.40(17) . . ?
C4 C5 C6 119.74(16) . . ?
C7 C5 C6 116.86(17) . . ?
N2 C6 C5 122.21(16) . . ?
N2 C6 C1 117.83(15) . . ?
C5 C6 C1 119.95(16) . . ?
C8 C7 C5 120.18(17) . . ?
C8 C7 H7 119.9 . . ?
C5 C7 H7 119.9 . . ?
C7 C8 C9 119.69(17) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
N2 C9 C8 121.99(18) . . ?
N2 C9 C10 118.30(16) . . ?
C8 C9 C10 119.70(17) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C11 C25 124.89(15) . 2_556 ?
O1 C11 C12 115.73(15) . . ?
C25 C11 C12 119.33(15) 2_556 . ?
C13 C12 C17 118.55(17) . . ?
C13 C12 C11 118.02(16) . . ?
C17 C12 C11 123.39(17) . . ?
C14 C13 C12 121.02(18) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 119.43(19) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 120.7(2) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C12 120.1(2) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?
N1 C18 C25 122.61(16) . . ?
N1 C18 C19 122.78(15) . . ?
C25 C18 C19 114.47(14) . . ?
C24 C19 C20 119.20(17) . . ?
C24 C19 C18 119.97(16) . . ?
C20 C19 C18 120.69(16) . . ?
C21 C20 C19 119.69(19) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 120.6(2) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 119.9(2) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 119.9(2) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C23 C24 C19 120.70(19) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?
C11 C25 C18 126.43(16) 2_556 . ?
C11 C25 H25 116.8 2_556 . ?
C18 C25 H25 116.8 . . ?

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
C27A Cl3 C27 Cl4 8(2) . . . . ?
C27B Cl3 C27 Cl4 -135(10) . . . . ?
C27 Cl3 C27A Cl4A 174(5) . . . . ?
C27B Cl3 C27A Cl4A -173.4(18) . . . . ?
Cl4A Cl4A C27A Cl3 -87.8(11) 7_556 . . . ?
C27A Cl3 C27B Cl4B 19.1(10) . . . . ?
C27 Cl3 C27B Cl4B 45(7) . . . . ?
O1 Zn1 O1 C11 121.88(14) 2_556 . . . ?
N1 Zn1 O1 C11 -153.71(14) . . . . ?
N1 Zn1 O1 C11 34.34(13) 2_556 . . . ?
N2 Zn1 O1 C11 27.9(2) 2_556 . . . ?
N2 Zn1 O1 C11 -76.86(14) . . . . ?
O1 Zn1 N1 C18 -125.66(14) . . . . ?
O1 Zn1 N1 C18 -29.23(14) 2_556 . . . ?
N1 Zn1 N1 C18 -77.57(14) 2_556 . . . ?
N2 Zn1 N1 C18 53.78(15) 2_556 . . . ?
N2 Zn1 N1 C18 148.66(15) . . . . ?
O1 Zn1 N1 C1 58.39(11) . . . . ?
O1 Zn1 N1 C1 154.82(11) 2_556 . . . ?
N1 Zn1 N1 C1 106.48(11) 2_556 . . . ?
N2 Zn1 N1 C1 -122.17(11) 2_556 . . . ?
N2 Zn1 N1 C1 -27.29(11) . . . . ?
O1 Zn1 N2 C9 96.06(16) . . . . ?
O1 Zn1 N2 C9 -168.19(15) 2_556 . . . ?
N1 Zn1 N2 C9 -174.76(16) . . . . ?
N1 Zn1 N2 C9 13.55(17) 2_556 . . . ?
N2 Zn1 N2 C9 -65.63(15) 2_556 . . . ?
O1 Zn1 N2 C6 -62.20(11) . . . . ?
O1 Zn1 N2 C6 33.5(2) 2_556 . . . ?
N1 Zn1 N2 C6 26.98(11) . . . . ?
N1 Zn1 N2 C6 -144.71(11) 2_556 . . . ?
N2 Zn1 N2 C6 136.12(12) 2_556 . . . ?
C18 N1 C1 C2 35.0(3) . . . . ?
Zn1 N1 C1 C2 -148.94(15) . . . . ?
C18 N1 C1 C6 -151.89(16) . . . . ?
Zn1 N1 C1 C6 24.18(18) . . . . ?
N1 C1 C2 C3 176.60(17) . . . . ?
C6 C1 C2 C3 3.6(3) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 -2.0(3) . . . . ?
C3 C4 C5 C7 179.78(19) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C9 N2 C6 C5 -4.1(3) . . . . ?
Zn1 N2 C6 C5 156.94(14) . . . . ?
C9 N2 C6 C1 175.87(16) . . . . ?
Zn1 N2 C6 C1 -23.07(18) . . . . ?
C4 C5 C6 N2 -175.76(17) . . . . ?
C7 C5 C6 N2 4.1(3) . . . . ?
C4 C5 C6 C1 4.2(3) . . . . ?
C7 C5 C6 C1 -175.85(17) . . . . ?
C2 C1 C6 N2 174.19(16) . . . . ?
N1 C1 C6 N2 0.5(2) . . . . ?
C2 C1 C6 C5 -5.8(3) . . . . ?
N1 C1 C6 C5 -179.49(15) . . . . ?
C4 C5 C7 C8 178.63(19) . . . . ?
C6 C5 C7 C8 -1.3(3) . . . . ?
C5 C7 C8 C9 -1.5(3) . . . . ?
C6 N2 C9 C8 1.2(3) . . . . ?
Zn1 N2 C9 C8 -155.05(14) . . . . ?
C6 N2 C9 C10 -177.87(16) . . . . ?
Zn1 N2 C9 C10 25.9(2) . . . . ?
C7 C8 C9 N2 1.6(3) . . . . ?
C7 C8 C9 C10 -179.36(19) . . . . ?
Zn1 O1 C11 C25 -27.1(2) . . . 2_556 ?
Zn1 O1 C11 C12 150.31(12) . . . . ?
O1 C11 C12 C13 -26.7(2) . . . . ?
C25 C11 C12 C13 150.91(17) 2_556 . . . ?
O1 C11 C12 C17 155.58(19) . . . . ?
C25 C11 C12 C17 -26.8(3) 2_556 . . . ?
C17 C12 C13 C14 0.7(3) . . . . ?
C11 C12 C13 C14 -177.11(17) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C14 C15 C16 C17 0.5(4) . . . . ?
C15 C16 C17 C12 -0.6(4) . . . . ?
C13 C12 C17 C16 0.0(3) . . . . ?
C11 C12 C17 C16 177.7(2) . . . . ?
C1 N1 C18 C25 -167.92(16) . . . . ?
Zn1 N1 C18 C25 16.6(2) . . . . ?
C1 N1 C18 C19 16.7(3) . . . . ?
Zn1 N1 C18 C19 -158.80(12) . . . . ?
N1 C18 C19 C24 -132.75(18) . . . . ?
C25 C18 C19 C24 51.5(2) . . . . ?
N1 C18 C19 C20 51.5(2) . . . . ?
C25 C18 C19 C20 -124.28(18) . . . . ?
C24 C19 C20 C21 -0.7(3) . . . . ?
C18 C19 C20 C21 175.13(17) . . . . ?
C19 C20 C21 C22 1.2(3) . . . . ?
C20 C21 C22 C23 -0.6(3) . . . . ?
C21 C22 C23 C24 -0.6(3) . . . . ?
C22 C23 C24 C19 1.1(3) . . . . ?
C20 C19 C24 C23 -0.4(3) . . . . ?
C18 C19 C24 C23 -176.28(16) . . . . ?
N1 C18 C25 C11 5.7(3) . . . 2_556 ?
C19 C18 C25 C11 -178.57(17) . . . 2_556 ?

_diffrn_measured_fraction_theta_max 0.937
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.949
_refine_diff_density_min         -1.097
_refine_diff_density_rms         0.080
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 0.000 147 19 ' '
2 0.000 0.500 0.000 147 19 ' '
3 1.000 0.202 0.250 21 0 ' '
4 0.500 0.702 0.250 21 0 ' '
5 0.500 0.000 0.500 147 19 ' '
6 1.000 0.500 0.500 147 19 ' '
7 0.500 0.297 0.750 21 0 ' '
8 1.000 0.797 0.750 21 0 ' '
_platon_squeeze_details          
;
an unidentified solvent molecule was squeezed from final refinements
;
_chemical_properties_physical    Air-sensitive
_database_code_depnum_ccdc_archive 'CCDC 1005747'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_frit15a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H20 F6 N4 O2 Zn'
_chemical_formula_sum            'C28 H20 F6 N4 O2 Zn'
_chemical_formula_weight         623.85

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Cc

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                   10.9999(5)
_cell_length_b                   21.1507(11)
_cell_length_c                   12.5158(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.9640(10)
_cell_angle_gamma                90.00
_cell_volume                     2681.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9941
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      25.36

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1264
_exptl_absorpt_coefficient_mu    0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8417
_exptl_absorpt_correction_T_max  0.8655
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'doubly curved mirror'
_diffrn_measurement_device_type  'Bruker CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16741
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         25.36
_reflns_number_total             4616
_reflns_number_gt                4415
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0219P)²+2.5845P] where P=(Fo²+2Fc²)/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   0.002(8)
_refine_ls_number_reflns         4616
_refine_ls_number_parameters     370
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0273
_refine_ls_wR_factor_ref         0.0635
_refine_ls_wR_factor_gt          0.0623
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.002
_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 0.28560(3) 0.666138(12) 0.31491(3) 0.01638(8) Uani 1 1 d . . .
F1 F 0.1803(5) 0.7419(2) 0.6171(4) 0.0402(5) Uani 0.475(4) 1 d PD A 1
F2 F 0.0819(5) 0.8048(2) 0.4728(4) 0.0402(5) Uani 0.475(4) 1 d PD A 1
F3 F -0.0296(6) 0.7372(3) 0.5291(6) 0.0402(5) Uani 0.475(4) 1 d PD A 1
F1' F 0.1778(5) 0.7659(2) 0.5956(4) 0.0402(5) Uani 0.525(4) 1 d PD A 2
F2' F 0.0115(5) 0.79660(18) 0.4441(4) 0.0402(5) Uani 0.525(4) 1 d PD A 2
F3' F -0.0147(6) 0.7212(2) 0.5492(5) 0.0402(5) Uani 0.525(4) 1 d PD A 2
F4 F 0.62061(17) 0.51847(8) 0.55477(16) 0.0351(4) Uani 1 1 d . . .
F5 F 0.74039(16) 0.54069(8) 0.45906(18) 0.0350(4) Uani 1 1 d . . .
F6 F 0.55217(17) 0.49446(8) 0.37412(16) 0.0338(4) Uani 1 1 d . . .
O1 O 0.22614(17) 0.69482(9) 0.44547(16) 0.0205(4) Uani 1 1 d . . .
O2 O 0.42470(18) 0.59970(9) 0.41105(17) 0.0200(4) Uani 1 1 d . . .
N1 N 0.1198(2) 0.60218(10) 0.2678(2) 0.0177(5) Uani 1 1 d . . .
N2 N 0.2895(2) 0.61856(10) 0.16329(19) 0.0165(5) Uani 1 1 d . . .
N3 N 0.4451(2) 0.73177(10) 0.3598(2) 0.0175(5) Uani 1 1 d . . .
N4 N 0.1895(2) 0.75245(10) 0.22779(19) 0.0177(5) Uani 1 1 d . . .
C1 C 0.0761(3) 0.74529(14) 0.5078(3) 0.0294(7) Uani 1 1 d D . .
C2 C 0.1050(3) 0.69714(12) 0.4297(2) 0.0209(6) Uani 1 1 d . A .
C3 C 0.0000(3) 0.66447(12) 0.3530(3) 0.0212(6) Uani 1 1 d . . .
H3A H -0.0848 0.6740 0.3521 0.025 Uiso 1 1 calc R A .
C4 C 0.0068(3) 0.61710(13) 0.2739(3) 0.0204(6) Uani 1 1 d . A .
C5 C -0.1247(3) 0.58810(14) 0.1977(3) 0.0291(7) Uani 1 1 d . . .
H5A H -0.1203 0.5731 0.1252 0.044 Uiso 1 1 calc R A .
H5B H -0.1944 0.6200 0.1803 0.044 Uiso 1 1 calc R . .
H5C H -0.1443 0.5525 0.2385 0.044 Uiso 1 1 calc R . .
C6 C 0.1344(3) 0.55180(12) 0.2005(2) 0.0191(6) Uani 1 1 d . . .
C7 C 0.0779(3) 0.49260(14) 0.1919(3) 0.0253(6) Uani 1 1 d . . .
H7A H 0.0229 0.4839 0.2327 0.030 Uiso 1 1 calc R . .
C8 C 0.1011(3) 0.44498(14) 0.1231(3) 0.0290(7) Uani 1 1 d . . .
H8A H 0.0600 0.4049 0.1175 0.035 Uiso 1 1 calc R . .
C9 C 0.1811(3) 0.45499(14) 0.0645(3) 0.0256(6) Uani 1 1 d . . .
H9A H 0.1938 0.4225 0.0174 0.031 Uiso 1 1 calc R . .
C10 C 0.2449(3) 0.51388(13) 0.0741(2) 0.0211(6) Uani 1 1 d . . .
C11 C 0.3289(3) 0.52807(14) 0.0168(3) 0.0261(6) Uani 1 1 d . . .
H11A H 0.3427 0.4978 -0.0334 0.031 Uiso 1 1 calc R . .
C12 C 0.3906(3) 0.58527(14) 0.0334(3) 0.0252(6) Uani 1 1 d . . .
H12A H 0.4464 0.5956 -0.0059 0.030 Uiso 1 1 calc R . .
C13 C 0.3699(3) 0.62931(12) 0.1105(3) 0.0215(6) Uani 1 1 d . . .
H13A H 0.4163 0.6683 0.1245 0.026 Uiso 1 1 calc R . .
C14 C 0.2238(2) 0.56168(12) 0.1452(2) 0.0179(5) Uani 1 1 d . . .
C15 C 0.6156(3) 0.53963(13) 0.4520(3) 0.0254(6) Uani 1 1 d . . .
C16 C 0.5429(3) 0.60307(13) 0.4185(2) 0.0206(6) Uani 1 1 d . . .
C17 C 0.6121(3) 0.65319(13) 0.3995(3) 0.0231(6) Uani 1 1 d . . .
H17A H 0.6989 0.6447 0.4045 0.028 Uiso 1 1 calc R . .
C18 C 0.5656(3) 0.71639(13) 0.3732(2) 0.0198(6) Uani 1 1 d . . .
C19 C 0.6643(3) 0.76280(13) 0.3612(3) 0.0266(7) Uani 1 1 d . . .
H19A H 0.6171 0.7977 0.3104 0.040 Uiso 1 1 calc R . .
H19B H 0.7201 0.7412 0.3277 0.040 Uiso 1 1 calc R . .
H19C H 0.7197 0.7795 0.4379 0.040 Uiso 1 1 calc R . .
C20 C 0.4002(3) 0.79491(12) 0.3491(2) 0.0178(6) Uani 1 1 d . . .
C21 C 0.4735(3) 0.84638(14) 0.4092(3) 0.0218(6) Uani 1 1 d . . .
H21A H 0.5627 0.8404 0.4611 0.026 Uiso 1 1 calc R . .
C22 C 0.4177(3) 0.90734(13) 0.3945(3) 0.0225(6) Uani 1 1 d . . .
H22A H 0.4708 0.9421 0.4343 0.027 Uiso 1 1 calc R . .
C23 C 0.2895(3) 0.91729(11) 0.3245(3) 0.0208(5) Uani 1 1 d . . .
H23A H 0.2543 0.9589 0.3141 0.025 Uiso 1 1 calc R . .
C24 C 0.2078(3) 0.86577(12) 0.2668(2) 0.0191(6) Uani 1 1 d . . .
C25 C 0.0709(3) 0.87157(14) 0.1995(3) 0.0222(6) Uani 1 1 d . . .
H25A H 0.0295 0.9118 0.1898 0.027 Uiso 1 1 calc R . .
C26 C -0.0018(3) 0.81947(13) 0.1484(2) 0.0218(6) Uani 1 1 d . . .
H26A H -0.0937 0.8229 0.1029 0.026 Uiso 1 1 calc R . .
C27 C 0.0623(3) 0.76058(13) 0.1647(2) 0.0217(6) Uani 1 1 d . . .
H27A H 0.0113 0.7246 0.1283 0.026 Uiso 1 1 calc R . .
C28 C 0.2636(3) 0.80451(12) 0.2792(2) 0.0167(6) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.0737(19) . ?
Zn1 O2 2.0801(18) . ?
Zn1 N3 2.134(2) . ?
Zn1 N1 2.159(2) . ?
Zn1 N2 2.163(2) . ?
Zn1 N4 2.177(2) . ?
F1 C1 1.402(6) . ?
F2 C1 1.342(5) . ?
F3 C1 1.302(7) . ?
F1' C1 1.300(6) . ?
F2' C1 1.370(5) . ?
F3' C1 1.389(6) . ?
F4 C15 1.342(4) . ?
F5 C15 1.341(3) . ?
F6 C15 1.349(3) . ?
O1 C2 1.270(3) . ?
O2 C16 1.269(3) . ?
N1 C4 1.314(4) . ?
N1 C6 1.405(4) . ?
N2 C13 1.314(4) . ?
N2 C14 1.376(3) . ?
N3 C18 1.311(3) . ?
N3 C20 1.412(3) . ?
N4 C27 1.323(3) . ?
N4 C28 1.372(3) . ?
C1 C2 1.529(4) . ?
C2 C3 1.366(4) . ?
C3 C4 1.430(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.517(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.383(4) . ?
C6 C14 1.422(4) . ?
C7 C8 1.411(4) . ?
C7 H7A 0.9500 . ?
C8 C9 1.364(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.412(4) . ?
C9 H9A 0.9500 . ?
C10 C11 1.406(4) . ?
C10 C14 1.424(4) . ?
C11 C12 1.363(4) . ?
C11 H11A 0.9500 . ?
C12 C13 1.422(4) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C15 C16 1.534(4) . ?
C16 C17 1.378(4) . ?
C17 C18 1.423(4) . ?
C17 H17A 0.9500 . ?
C18 C19 1.514(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.389(4) . ?
C20 C28 1.428(4) . ?
C21 C22 1.409(4) . ?
C21 H21A 0.9500 . ?
C22 C23 1.355(4) . ?
C22 H22A 0.9500 . ?
C23 C24 1.418(4) . ?
C23 H23A 0.9500 . ?
C24 C28 1.416(4) . ?
C24 C25 1.415(4) . ?
C25 C26 1.365(4) . ?
C25 H25A 0.9500 . ?
C26 C27 1.406(4) . ?
C26 H26A 0.9500 . ?
C27 H27A 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
O1 Zn1 O2 97.40(8) . . ?
O1 Zn1 N3 94.70(8) . . ?
O2 Zn1 N3 86.75(8) . . ?
O1 Zn1 N1 84.63(8) . . ?
O2 Zn1 N1 94.99(8) . . ?
N3 Zn1 N1 178.19(9) . . ?
O1 Zn1 N2 161.39(7) . . ?
O2 Zn1 N2 86.06(8) . . ?
N3 Zn1 N2 103.77(9) . . ?
N1 Zn1 N2 76.85(8) . . ?
O1 Zn1 N4 84.76(8) . . ?
O2 Zn1 N4 163.74(7) . . ?
N3 Zn1 N4 77.00(8) . . ?
N1 Zn1 N4 101.26(8) . . ?
N2 Zn1 N4 97.05(8) . . ?
C2 O1 Zn1 121.54(17) . . ?
C16 O2 Zn1 120.40(18) . . ?
C4 N1 C6 123.3(2) . . ?
C4 N1 Zn1 123.44(18) . . ?
C6 N1 Zn1 110.94(17) . . ?
C13 N2 C14 118.8(2) . . ?
C13 N2 Zn1 127.45(18) . . ?
C14 N2 Zn1 111.25(17) . . ?
C18 N3 C20 123.1(2) . . ?
C18 N3 Zn1 124.00(18) . . ?
C20 N3 Zn1 111.66(16) . . ?
C27 N4 C28 118.2(2) . . ?
C27 N4 Zn1 127.00(18) . . ?
C28 N4 Zn1 110.77(16) . . ?
F3 C1 F1' 114.4(5) . . ?
F3 C1 F2' 85.5(3) . . ?
F1' C1 F2' 107.8(3) . . ?
F3 C1 F3' 17.4(3) . . ?
F1' C1 F3' 108.3(4) . . ?
F2' C1 F3' 102.8(3) . . ?
F3 C1 F1 104.4(4) . . ?
F1' C1 F1 24.0(2) . . ?
F2' C1 F1 130.4(3) . . ?
F3' C1 F1 92.9(4) . . ?
F3 C1 F2 110.5(3) . . ?
F1' C1 F2 80.0(3) . . ?
F2' C1 F2 31.5(2) . . ?
F3' C1 F2 126.8(3) . . ?
F1 C1 F2 104.0(3) . . ?
F3 C1 C2 118.0(4) . . ?
F1' C1 C2 116.1(3) . . ?
F2' C1 C2 110.2(3) . . ?
F3' C1 C2 110.7(3) . . ?
F1 C1 C2 107.2(3) . . ?
F2 C1 C2 111.6(3) . . ?
O1 C2 C3 129.6(3) . . ?
O1 C2 C1 113.2(2) . . ?
C3 C2 C1 117.2(2) . . ?
C2 C3 C4 125.6(2) . . ?
C2 C3 H3A 117.2 . . ?
C4 C3 H3A 117.2 . . ?
N1 C4 C3 121.0(2) . . ?
N1 C4 C5 123.9(3) . . ?
C3 C4 C5 115.1(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 N1 125.5(3) . . ?
C7 C6 C14 118.0(3) . . ?
N1 C6 C14 116.3(2) . . ?
C6 C7 C8 120.8(3) . . ?
C6 C7 H7A 119.6 . . ?
C8 C7 H7A 119.6 . . ?
C9 C8 C7 121.7(3) . . ?
C9 C8 H8A 119.2 . . ?
C7 C8 H8A 119.2 . . ?
C8 C9 C10 119.6(3) . . ?
C8 C9 H9A 120.2 . . ?
C10 C9 H9A 120.2 . . ?
C11 C10 C9 123.3(3) . . ?
C11 C10 C14 117.8(3) . . ?
C9 C10 C14 118.9(3) . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11A 120.0 . . ?
C10 C11 H11A 120.0 . . ?
C11 C12 C13 118.9(3) . . ?
C11 C12 H12A 120.6 . . ?
C13 C12 H12A 120.6 . . ?
N2 C13 C12 123.0(2) . . ?
N2 C13 H13A 118.5 . . ?
C12 C13 H13A 118.5 . . ?
N2 C14 C10 121.4(2) . . ?
N2 C14 C6 117.8(2) . . ?
C10 C14 C6 120.8(2) . . ?
F4 C15 F5 106.5(2) . . ?
F4 C15 F6 105.8(2) . . ?
F5 C15 F6 106.7(2) . . ?
F4 C15 C16 112.1(2) . . ?
F5 C15 C16 114.5(2) . . ?
F6 C15 C16 110.7(2) . . ?
O2 C16 C17 130.5(3) . . ?
O2 C16 C15 112.4(2) . . ?
C17 C16 C15 117.1(2) . . ?
C16 C17 C18 126.1(2) . . ?
C16 C17 H17A 116.9 . . ?
C18 C17 H17A 116.9 . . ?
N3 C18 C17 121.1(2) . . ?
N3 C18 C19 123.7(2) . . ?
C17 C18 C19 115.2(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 N3 125.6(3) . . ?
C21 C20 C28 118.1(2) . . ?
N3 C20 C28 116.0(2) . . ?
C20 C21 C22 121.0(3) . . ?
C20 C21 H21A 119.5 . . ?
C22 C21 H21A 119.5 . . ?
C23 C22 C21 121.2(3) . . ?
C23 C22 H22A 119.4 . . ?
C21 C22 H22A 119.4 . . ?
C22 C23 C24 120.2(2) . . ?
C22 C23 H23A 119.9 . . ?
C24 C23 H23A 119.9 . . ?
C28 C24 C25 117.4(2) . . ?
C28 C24 C23 119.0(3) . . ?
C25 C24 C23 123.5(3) . . ?
C26 C25 C24 120.1(3) . . ?
C26 C25 H25A 119.9 . . ?
C24 C25 H25A 119.9 . . ?
C25 C26 C27 118.5(3) . . ?
C25 C26 H26A 120.7 . . ?
C27 C26 H26A 120.7 . . ?
N4 C27 C26 123.8(3) . . ?
N4 C27 H27A 118.1 . . ?
C26 C27 H27A 118.1 . . ?
N4 C28 C24 122.0(2) . . ?
N4 C28 C20 117.7(2) . . ?
C24 C28 C20 120.3(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Zn1 O1 C2 -129.65(19) . . . . ?
N3 Zn1 O1 C2 143.02(19) . . . . ?
N1 Zn1 O1 C2 -35.3(2) . . . . ?
N2 Zn1 O1 C2 -29.9(4) . . . . ?
N4 Zn1 O1 C2 66.6(2) . . . . ?
O1 Zn1 O2 C16 -124.9(2) . . . . ?
N3 Zn1 O2 C16 -30.6(2) . . . . ?
N1 Zn1 O2 C16 149.8(2) . . . . ?
N2 Zn1 O2 C16 73.4(2) . . . . ?
N4 Zn1 O2 C16 -28.3(4) . . . . ?
O1 Zn1 N1 C4 37.2(2) . . . . ?
O2 Zn1 N1 C4 134.2(2) . . . . ?
N3 Zn1 N1 C4 -31(3) . . . . ?
N2 Zn1 N1 C4 -141.0(2) . . . . ?
N4 Zn1 N1 C4 -46.3(2) . . . . ?
O1 Zn1 N1 C6 -159.67(19) . . . . ?
O2 Zn1 N1 C6 -62.68(18) . . . . ?
N3 Zn1 N1 C6 132(3) . . . . ?
N2 Zn1 N1 C6 22.08(18) . . . . ?
N4 Zn1 N1 C6 116.78(18) . . . . ?
O1 Zn1 N2 C13 171.2(2) . . . . ?
O2 Zn1 N2 C13 -87.3(2) . . . . ?
N3 Zn1 N2 C13 -1.6(2) . . . . ?
N1 Zn1 N2 C13 176.7(2) . . . . ?
N4 Zn1 N2 C13 76.7(2) . . . . ?
O1 Zn1 N2 C14 -27.1(3) . . . . ?
O2 Zn1 N2 C14 74.42(17) . . . . ?
N3 Zn1 N2 C14 160.10(16) . . . . ?
N1 Zn1 N2 C14 -21.65(17) . . . . ?
N4 Zn1 N2 C14 -121.62(17) . . . . ?
O1 Zn1 N3 C18 130.8(2) . . . . ?
O2 Zn1 N3 C18 33.7(2) . . . . ?
N1 Zn1 N3 C18 -161(3) . . . . ?
N2 Zn1 N3 C18 -51.5(2) . . . . ?
N4 Zn1 N3 C18 -145.7(2) . . . . ?
O1 Zn1 N3 C20 -61.76(19) . . . . ?
O2 Zn1 N3 C20 -158.92(19) . . . . ?
N1 Zn1 N3 C20 6(3) . . . . ?
N2 Zn1 N3 C20 115.94(18) . . . . ?
N4 Zn1 N3 C20 21.75(18) . . . . ?
O1 Zn1 N4 C27 -82.9(2) . . . . ?
O2 Zn1 N4 C27 178.6(3) . . . . ?
N3 Zn1 N4 C27 -179.0(2) . . . . ?
N1 Zn1 N4 C27 0.6(2) . . . . ?
N2 Zn1 N4 C27 78.5(2) . . . . ?
O1 Zn1 N4 C28 73.79(17) . . . . ?
O2 Zn1 N4 C28 -24.7(4) . . . . ?
N3 Zn1 N4 C28 -22.27(17) . . . . ?
N1 Zn1 N4 C28 157.23(17) . . . . ?
N2 Zn1 N4 C28 -124.84(18) . . . . ?
Zn1 O1 C2 C3 24.9(4) . . . . ?
Zn1 O1 C2 C1 -153.53(18) . . . . ?
F3 C1 C2 O1 -156.7(4) . . . . ?
F1' C1 C2 O1 -15.4(4) . . . . ?
F2' C1 C2 O1 107.6(3) . . . . ?
F3' C1 C2 O1 -139.3(3) . . . . ?
F1 C1 C2 O1 -39.4(4) . . . . ?
F2 C1 C2 O1 73.8(4) . . . . ?
F3 C1 C2 C3 24.7(5) . . . . ?
F1' C1 C2 C3 166.0(4) . . . . ?
F2' C1 C2 C3 -71.1(4) . . . . ?
F3' C1 C2 C3 42.0(4) . . . . ?
F1 C1 C2 C3 142.0(3) . . . . ?
F2 C1 C2 C3 -104.8(4) . . . . ?
O1 C2 C3 C4 2.4(5) . . . . ?
C1 C2 C3 C4 -179.2(3) . . . . ?
C6 N1 C4 C3 173.3(3) . . . . ?
Zn1 N1 C4 C3 -25.6(4) . . . . ?
C6 N1 C4 C5 -8.6(4) . . . . ?
Zn1 N1 C4 C5 152.5(2) . . . . ?
C2 C3 C4 N1 -1.6(5) . . . . ?
C2 C3 C4 C5 -179.9(3) . . . . ?
C4 N1 C6 C7 -42.3(4) . . . . ?
Zn1 N1 C6 C7 154.5(2) . . . . ?
C4 N1 C6 C14 143.2(3) . . . . ?
Zn1 N1 C6 C14 -19.9(3) . . . . ?
N1 C6 C7 C8 -178.9(3) . . . . ?
C14 C6 C7 C8 -4.5(4) . . . . ?
C6 C7 C8 C9 1.1(5) . . . . ?
C7 C8 C9 C10 1.3(5) . . . . ?
C8 C9 C10 C11 179.9(3) . . . . ?
C8 C9 C10 C14 -0.1(4) . . . . ?
C9 C10 C11 C12 -177.8(3) . . . . ?
C14 C10 C11 C12 2.2(4) . . . . ?
C10 C11 C12 C13 1.0(4) . . . . ?
C14 N2 C13 C12 1.2(4) . . . . ?
Zn1 N2 C13 C12 161.7(2) . . . . ?
C11 C12 C13 N2 -2.9(4) . . . . ?
C13 N2 C14 C10 2.3(4) . . . . ?
Zn1 N2 C14 C10 -161.2(2) . . . . ?
C13 N2 C14 C6 -178.2(2) . . . . ?
Zn1 N2 C14 C6 18.3(3) . . . . ?
C11 C10 C14 N2 -4.0(4) . . . . ?
C9 C10 C14 N2 176.1(2) . . . . ?
C11 C10 C14 C6 176.5(3) . . . . ?
C9 C10 C14 C6 -3.4(4) . . . . ?
C7 C6 C14 N2 -173.8(2) . . . . ?
N1 C6 C14 N2 1.1(4) . . . . ?
C7 C6 C14 C10 5.7(4) . . . . ?
N1 C6 C14 C10 -179.4(2) . . . . ?
Zn1 O2 C16 C17 19.9(4) . . . . ?
Zn1 O2 C16 C15 -158.81(18) . . . . ?
F4 C15 C16 O2 -59.6(3) . . . . ?
F5 C15 C16 O2 179.0(2) . . . . ?
F6 C15 C16 O2 58.3(3) . . . . ?
F4 C15 C16 C17 121.5(3) . . . . ?
F5 C15 C16 C17 0.0(4) . . . . ?
F6 C15 C16 C17 -120.6(3) . . . . ?
O2 C16 C17 C18 4.5(5) . . . . ?
C15 C16 C17 C18 -176.8(3) . . . . ?
C20 N3 C18 C17 171.3(3) . . . . ?
Zn1 N3 C18 C17 -22.7(4) . . . . ?
C20 N3 C18 C19 -9.3(4) . . . . ?
Zn1 N3 C18 C19 156.7(2) . . . . ?
C16 C17 C18 N3 -2.9(5) . . . . ?
C16 C17 C18 C19 177.6(3) . . . . ?
C18 N3 C20 C21 -38.0(4) . . . . ?
Zn1 N3 C20 C21 154.5(2) . . . . ?
C18 N3 C20 C28 148.9(3) . . . . ?
Zn1 N3 C20 C28 -18.7(3) . . . . ?
N3 C20 C21 C22 -178.1(3) . . . . ?
C28 C20 C21 C22 -5.0(4) . . . . ?
C20 C21 C22 C23 2.4(5) . . . . ?
C21 C22 C23 C24 1.7(5) . . . . ?
C22 C23 C24 C28 -2.8(4) . . . . ?
C22 C23 C24 C25 175.0(3) . . . . ?
C28 C24 C25 C26 -0.8(4) . . . . ?
C23 C24 C25 C26 -178.6(3) . . . . ?
C24 C25 C26 C27 0.2(4) . . . . ?
C28 N4 C27 C26 -0.8(4) . . . . ?
Zn1 N4 C27 C26 154.4(2) . . . . ?
C25 C26 C27 N4 0.6(4) . . . . ?
C27 N4 C28 C24 0.1(4) . . . . ?
Zn1 N4 C28 C24 -158.8(2) . . . . ?
C27 N4 C28 C20 178.7(2) . . . . ?
Zn1 N4 C28 C20 19.7(3) . . . . ?
C25 C24 C28 N4 0.6(4) . . . . ?
C23 C24 C28 N4 178.6(3) . . . . ?
C25 C24 C28 C20 -177.9(3) . . . . ?
C23 C24 C28 C20 0.0(4) . . . . ?
C21 C20 C28 N4 -174.8(2) . . . . ?
N3 C20 C28 N4 -1.1(4) . . . . ?
C21 C20 C28 C24 3.8(4) . . . . ?
N3 C20 C28 C24 177.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.055
_database_code_depnum_ccdc_archive 'CCDC 1005748'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_frit10

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H32 F6 N4 O2 Zn'
_chemical_formula_weight         708.01

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   13.728(2)
_cell_length_b                   15.472(2)
_cell_length_c                   15.449(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.124(2)
_cell_angle_gamma                90.00
_cell_volume                     3195.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5577
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      24.59

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1456
_exptl_absorpt_coefficient_mu    0.842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.549
_exptl_absorpt_correction_T_max  0.777
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            22551
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_av_sigmaI/netI    0.0646
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         24.78
_reflns_number_total             5445
_reflns_number_gt                4115
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0426P)²+19.2625P] where P=(Fo²+2Fc²)/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         5445
_refine_ls_number_parameters     430
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1605
_refine_ls_wR_factor_gt          0.1469
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001

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 0.38028(5) 0.14251(4) 0.23559(4) 0.01797(18) Uani 1 1 d . . .
F1 F 0.3955(3) 0.0287(2) -0.0447(2) 0.0340(8) Uani 1 1 d . . .
F2 F 0.3527(3) 0.1510(2) -0.1085(2) 0.0367(9) Uani 1 1 d . . .
F3 F 0.5079(3) 0.1203(2) -0.0579(2) 0.0345(8) Uani 1 1 d . . .
F4 F 0.2950(3) 0.0656(2) 0.5337(2) 0.0354(8) Uani 1 1 d . . .
F5 F 0.4508(2) 0.0706(2) 0.5371(2) 0.0354(8) Uani 1 1 d . . .
F6 F 0.3754(3) 0.1833(2) 0.5715(2) 0.0360(9) Uani 1 1 d . . .
O1 O 0.4428(3) 0.2601(2) 0.2104(2) 0.0221(8) Uani 1 1 d . . .
O2 O 0.2406(3) 0.1940(2) 0.2358(2) 0.0214(8) Uani 1 1 d . . .
N2 N 0.3118(3) 0.0173(3) 0.2195(3) 0.0199(10) Uani 1 1 d . . .
N1 N 0.3515(3) 0.1240(3) 0.0977(3) 0.0186(10) Uani 1 1 d . . .
N4 N 0.5332(3) 0.0969(3) 0.2787(3) 0.0219(10) Uani 1 1 d . . .
C1 C 0.2957(4) -0.0353(3) 0.2828(4) 0.0221(12) Uani 1 1 d . . .
H1 H 0.3337 -0.0270 0.3417 0.026 Uiso 1 1 calc R . .
C2 C 0.2257(4) -0.1023(3) 0.2670(4) 0.0235(12) Uani 1 1 d . . .
H2 H 0.2184 -0.1401 0.3136 0.028 Uiso 1 1 calc R . .
C3 C 0.1677(4) -0.1125(4) 0.1828(4) 0.0257(13) Uani 1 1 d . . .
H3 H 0.1193 -0.1573 0.1705 0.031 Uiso 1 1 calc R . .
C4 C 0.1803(4) -0.0560(3) 0.1149(4) 0.0238(12) Uani 1 1 d . . .
C5 C 0.2552(4) 0.0074(3) 0.1356(3) 0.0208(12) Uani 1 1 d . . .
C6 C 0.2725(4) 0.0658(3) 0.0698(4) 0.0214(12) Uani 1 1 d . . .
C7 C 0.4125(4) 0.1526(3) 0.0494(4) 0.0231(12) Uani 1 1 d . . .
C8 C 0.4809(4) 0.2199(3) 0.0751(3) 0.0222(12) Uani 1 1 d . . .
H8 H 0.5243 0.2322 0.0367 0.027 Uiso 1 1 calc R . .
C9 C 0.4921(4) 0.2711(3) 0.1516(4) 0.0217(12) Uani 1 1 d . . .
C10 C 0.5693(4) 0.3447(4) 0.1654(4) 0.0260(13) Uani 1 1 d . . .
C11 C 0.6723(5) 0.3074(5) 0.1672(5) 0.0483(19) Uani 1 1 d . . .
H11A H 0.6711 0.2778 0.1109 0.072 Uiso 1 1 calc R . .
H11B H 0.6904 0.2661 0.2164 0.072 Uiso 1 1 calc R . .
H11C H 0.7216 0.3542 0.1756 0.072 Uiso 1 1 calc R . .
C12 C 0.5408(6) 0.4094(4) 0.0912(4) 0.0453(18) Uani 1 1 d . . .
H12A H 0.5858 0.4593 0.1034 0.068 Uiso 1 1 calc R . .
H12B H 0.4718 0.4285 0.0868 0.068 Uiso 1 1 calc R . .
H12C H 0.5462 0.3825 0.0350 0.068 Uiso 1 1 calc R . .
C13 C 0.5706(5) 0.3906(5) 0.2531(4) 0.0434(18) Uani 1 1 d . . .
H13A H 0.6160 0.4402 0.2595 0.065 Uiso 1 1 calc R . .
H13B H 0.5937 0.3504 0.3025 0.065 Uiso 1 1 calc R . .
H13C H 0.5030 0.4106 0.2536 0.065 Uiso 1 1 calc R . .
C14 C 0.4169(5) 0.1133(4) -0.0398(4) 0.0295(14) Uani 1 1 d . . .
C15 C 0.2072(4) 0.0644(4) -0.0125(4) 0.0246(12) Uani 1 1 d . . .
H15 H 0.2139 0.1059 -0.0561 0.029 Uiso 1 1 calc R . .
C16 C 0.1311(5) 0.0022(4) -0.0321(4) 0.0313(14) Uani 1 1 d . . .
H16 H 0.0867 0.0025 -0.0890 0.038 Uiso 1 1 calc R . .
C17 C 0.1191(4) -0.0588(4) 0.0286(4) 0.0283(13) Uani 1 1 d . . .
H17 H 0.0699 -0.1027 0.0125 0.034 Uiso 1 1 calc R . .
N3 N 0.4112(3) 0.1606(3) 0.3742(3) 0.0210(10) Uani 1 1 d . . .
C19 C 0.5148(4) 0.1668(3) 0.4094(3) 0.0201(12) Uani 1 1 d . . .
C20 C 0.5573(4) 0.2121(3) 0.4863(3) 0.0224(12) Uani 1 1 d . . .
H20 H 0.5154 0.2398 0.5191 0.027 Uiso 1 1 calc R . .
C21 C 0.6623(5) 0.2174(4) 0.5162(4) 0.0285(13) Uani 1 1 d . . .
H21 H 0.6905 0.2478 0.5694 0.034 Uiso 1 1 calc R . .
C22 C 0.7230(4) 0.1792(4) 0.4693(4) 0.0284(14) Uani 1 1 d . . .
H22 H 0.7935 0.1814 0.4908 0.034 Uiso 1 1 calc R . .
C23 C 0.6822(4) 0.1365(4) 0.3891(4) 0.0236(12) Uani 1 1 d . . .
C24 C 0.5769(4) 0.1336(3) 0.3595(3) 0.0241(12) Uani 1 1 d . . .
C25 C 0.5897(4) 0.0618(4) 0.2305(4) 0.0286(13) Uani 1 1 d . . .
H25 H 0.5580 0.0372 0.1749 0.034 Uiso 1 1 calc R . .
C26 C 0.6949(5) 0.0587(4) 0.2566(4) 0.0343(15) Uani 1 1 d . . .
H26 H 0.7331 0.0307 0.2207 0.041 Uiso 1 1 calc R . .
C27 C 0.7402(4) 0.0968(4) 0.3344(4) 0.0291(14) Uani 1 1 d . . .
H27 H 0.8111 0.0970 0.3526 0.035 Uiso 1 1 calc R . .
C28 C 0.3409(4) 0.1461(3) 0.4180(3) 0.0216(12) Uani 1 1 d . . .
C29 C 0.2385(4) 0.1528(3) 0.3820(3) 0.0214(12) Uani 1 1 d . . .
H29 H 0.1951 0.1377 0.4195 0.026 Uiso 1 1 calc R . .
C30 C 0.1935(4) 0.1795(3) 0.2958(4) 0.0225(12) Uani 1 1 d . . .
C31 C 0.0801(4) 0.1917(3) 0.2686(4) 0.0213(12) Uani 1 1 d . . .
C32 C 0.0247(4) 0.1671(4) 0.3403(4) 0.0304(14) Uani 1 1 d . . .
H32A H -0.0471 0.1775 0.3183 0.046 Uiso 1 1 calc R . .
H32B H 0.0497 0.2022 0.3935 0.046 Uiso 1 1 calc R . .
H32C H 0.0360 0.1058 0.3552 0.046 Uiso 1 1 calc R . .
C33 C 0.0595(4) 0.2874(4) 0.2452(4) 0.0271(13) Uani 1 1 d . . .
H33A H 0.0886 0.3027 0.1949 0.041 Uiso 1 1 calc R . .
H33B H 0.0895 0.3232 0.2966 0.041 Uiso 1 1 calc R . .
H33C H -0.0129 0.2973 0.2290 0.041 Uiso 1 1 calc R . .
C34 C 0.0399(4) 0.1361(4) 0.1868(4) 0.0277(13) Uani 1 1 d . . .
H34A H 0.0498 0.0749 0.2028 0.041 Uiso 1 1 calc R . .
H34B H 0.0758 0.1501 0.1405 0.041 Uiso 1 1 calc R . .
H34C H -0.0316 0.1475 0.1645 0.041 Uiso 1 1 calc R . .
C35 C 0.3664(4) 0.1167(4) 0.5148(4) 0.0249(13) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O2 2.077(4) . ?
Zn1 O1 2.086(4) . ?
Zn1 N1 2.096(4) . ?
Zn1 N3 2.105(4) . ?
Zn1 N2 2.144(4) . ?
Zn1 N4 2.172(5) . ?
F1 C14 1.340(6) . ?
F2 C14 1.349(7) . ?
F3 C14 1.344(7) . ?
F4 C35 1.342(6) . ?
F5 C35 1.338(6) . ?
F6 C35 1.339(7) . ?
O1 C9 1.261(6) . ?
O2 C30 1.264(6) . ?
N2 C1 1.329(7) . ?
N2 C5 1.359(7) . ?
N1 C7 1.319(7) . ?
N1 C6 1.400(7) . ?
N4 C25 1.309(7) . ?
N4 C24 1.378(7) . ?
C1 C2 1.397(8) . ?
C2 C3 1.371(8) . ?
C3 C4 1.406(8) . ?
C4 C17 1.407(8) . ?
C4 C5 1.405(8) . ?
C5 C6 1.421(7) . ?
C6 C15 1.379(8) . ?
C7 C8 1.398(8) . ?
C7 C14 1.520(8) . ?
C8 C9 1.402(7) . ?
C9 C10 1.537(7) . ?
C10 C12 1.506(8) . ?
C10 C11 1.521(9) . ?
C10 C13 1.526(8) . ?
C15 C16 1.402(8) . ?
C16 C17 1.366(8) . ?
N3 C28 1.317(7) . ?
N3 C19 1.406(7) . ?
C19 C24 1.372(8) . ?
C19 C20 1.389(7) . ?
C20 C21 1.412(8) . ?
C21 C22 1.358(8) . ?
C22 C23 1.404(8) . ?
C23 C24 1.414(8) . ?
C23 C27 1.424(8) . ?
C25 C26 1.410(8) . ?
C26 C27 1.357(9) . ?
C28 C29 1.394(8) . ?
C28 C35 1.526(7) . ?
C29 C30 1.397(7) . ?
C30 C31 1.530(8) . ?
C31 C34 1.525(7) . ?
C31 C32 1.528(8) . ?
C31 C33 1.534(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Zn1 O1 94.87(14) . . ?
O2 Zn1 N1 95.31(15) . . ?
O1 Zn1 N1 85.41(15) . . ?
O2 Zn1 N3 85.44(15) . . ?
O1 Zn1 N3 94.44(15) . . ?
N1 Zn1 N3 179.24(18) . . ?
O2 Zn1 N2 88.05(15) . . ?
O1 Zn1 N2 162.78(15) . . ?
N1 Zn1 N2 77.42(16) . . ?
N3 Zn1 N2 102.71(17) . . ?
O2 Zn1 N4 162.33(15) . . ?
O1 Zn1 N4 86.04(16) . . ?
N1 Zn1 N4 102.35(16) . . ?
N3 Zn1 N4 76.89(16) . . ?
N2 Zn1 N4 96.30(17) . . ?
C9 O1 Zn1 124.2(3) . . ?
C30 O2 Zn1 124.0(3) . . ?
C1 N2 C5 118.6(5) . . ?
C1 N2 Zn1 127.6(4) . . ?
C5 N2 Zn1 110.7(3) . . ?
C7 N1 C6 126.0(5) . . ?
C7 N1 Zn1 122.1(4) . . ?
C6 N1 Zn1 110.8(3) . . ?
C25 N4 C24 119.6(5) . . ?
C25 N4 Zn1 128.0(4) . . ?
C24 N4 Zn1 109.6(3) . . ?
N2 C1 C2 123.2(5) . . ?
C3 C2 C1 118.6(5) . . ?
C2 C3 C4 119.6(5) . . ?
C17 C4 C5 119.1(5) . . ?
C17 C4 C3 122.7(5) . . ?
C5 C4 C3 118.1(5) . . ?
N2 C5 C4 121.7(5) . . ?
N2 C5 C6 117.3(5) . . ?
C4 C5 C6 120.9(5) . . ?
C15 C6 N1 126.1(5) . . ?
C15 C6 C5 118.1(5) . . ?
N1 C6 C5 115.6(5) . . ?
N1 C7 C8 124.1(5) . . ?
N1 C7 C14 122.7(5) . . ?
C8 C7 C14 113.2(5) . . ?
C7 C8 C9 126.7(5) . . ?
O1 C9 C8 123.9(5) . . ?
O1 C9 C10 117.8(5) . . ?
C8 C9 C10 118.4(5) . . ?
C12 C10 C11 110.3(5) . . ?
C12 C10 C13 108.4(5) . . ?
C11 C10 C13 109.7(5) . . ?
C12 C10 C9 109.6(5) . . ?
C11 C10 C9 109.2(5) . . ?
C13 C10 C9 109.7(5) . . ?
F3 C14 F1 105.6(5) . . ?
F3 C14 F2 105.8(4) . . ?
F1 C14 F2 106.4(5) . . ?
F3 C14 C7 112.7(5) . . ?
F1 C14 C7 112.9(5) . . ?
F2 C14 C7 112.7(5) . . ?
C6 C15 C16 120.4(5) . . ?
C17 C16 C15 121.8(5) . . ?
C16 C17 C4 119.3(5) . . ?
C28 N3 C19 127.4(5) . . ?
C28 N3 Zn1 119.8(4) . . ?
C19 N3 Zn1 110.8(3) . . ?
C24 C19 C20 118.4(5) . . ?
C24 C19 N3 117.3(5) . . ?
C20 C19 N3 123.9(5) . . ?
C19 C20 C21 120.5(5) . . ?
C22 C21 C20 120.3(5) . . ?
C21 C22 C23 120.4(5) . . ?
C22 C23 C24 118.3(5) . . ?
C22 C23 C27 124.2(5) . . ?
C24 C23 C27 117.6(5) . . ?
C19 C24 N4 117.7(5) . . ?
C19 C24 C23 121.8(5) . . ?
N4 C24 C23 120.5(5) . . ?
N4 C25 C26 123.5(6) . . ?
C27 C26 C25 118.1(6) . . ?
C26 C27 C23 120.5(5) . . ?
N3 C28 C29 125.0(5) . . ?
N3 C28 C35 121.5(5) . . ?
C29 C28 C35 113.5(5) . . ?
C30 C29 C28 126.1(5) . . ?
O2 C30 C29 124.2(5) . . ?
O2 C30 C31 115.8(5) . . ?
C29 C30 C31 120.0(5) . . ?
C34 C31 C32 108.3(5) . . ?
C34 C31 C30 108.2(4) . . ?
C32 C31 C30 114.4(5) . . ?
C34 C31 C33 109.7(5) . . ?
C32 C31 C33 108.5(5) . . ?
C30 C31 C33 107.8(4) . . ?
F5 C35 F6 107.2(4) . . ?
F5 C35 F4 105.2(4) . . ?
F6 C35 F4 105.9(4) . . ?
F5 C35 C28 113.8(4) . . ?
F6 C35 C28 112.2(5) . . ?
F4 C35 C28 111.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        24.78
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.112
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.101
_database_code_depnum_ccdc_archive 'CCDC 1005749'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_frit02

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H38 F6 N4 O3 Zn'
_chemical_formula_weight         850.15

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   11.8222(6)
_cell_length_b                   14.4520(8)
_cell_length_c                   23.0665(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.4910(10)
_cell_angle_gamma                90.00
_cell_volume                     3933.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9951
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      25.32

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1752
_exptl_absorpt_coefficient_mu    0.699
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.7484
_exptl_absorpt_correction_T_max  0.8283
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            34376
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         25.37
_reflns_number_total             7227
_reflns_number_gt                6109
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0600P)²+3.1000P] where P=(Fo²+2Fc²)/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         7227
_refine_ls_number_parameters     526
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1139
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.008
_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 0.89076(2) 0.337744(18) 0.171396(11) 0.02683(10) Uani 1 1 d . . .
F1 F 0.55310(12) 0.25517(11) 0.07607(6) 0.0432(4) Uani 1 1 d . . .
F2 F 0.55839(14) 0.11458(12) 0.10683(7) 0.0489(4) Uani 1 1 d . . .
F3 F 0.63125(13) 0.15010(12) 0.02689(7) 0.0456(4) Uani 1 1 d . . .
F4 F 1.12431(13) 0.59419(10) 0.28040(7) 0.0426(4) Uani 1 1 d . . .
F5 F 1.16192(15) 0.56387(11) 0.19266(7) 0.0515(4) Uani 1 1 d . . .
F6 F 1.25409(13) 0.49569(12) 0.26428(8) 0.0518(4) Uani 1 1 d . . .
O2 O 0.88024(14) 0.31646(11) 0.26074(7) 0.0296(4) Uani 1 1 d . . .
O1 O 0.96978(14) 0.21129(11) 0.15748(7) 0.0307(4) Uani 1 1 d . . .
O3 O 0.6017(3) 0.3114(3) -0.09633(14) 0.1025(11) Uani 1 1 d . . .
N1 N 0.74219(16) 0.26542(13) 0.15394(8) 0.0273(4) Uani 1 1 d . . .
N2 N 0.75715(17) 0.44500(13) 0.18181(8) 0.0282(4) Uani 1 1 d . . .
N4 N 0.95428(17) 0.38389(14) 0.08620(8) 0.0308(4) Uani 1 1 d . . .
N3 N 1.04536(16) 0.39699(14) 0.19504(8) 0.0291(4) Uani 1 1 d . . .
C1 C 0.7337(2) 0.20000(16) 0.11347(10) 0.0281(5) Uani 1 1 d . . .
C2 C 0.6192(2) 0.18014(18) 0.08124(11) 0.0355(6) Uani 1 1 d . . .
C3 C 0.8244(2) 0.14886(16) 0.09458(10) 0.0307(5) Uani 1 1 d . . .
H3 H 0.8102 0.1092 0.0632 0.037 Uiso 1 1 calc R . .
C4 C 0.9364(2) 0.15306(16) 0.11969(10) 0.0289(5) Uani 1 1 d . . .
C5 C 1.0236(2) 0.08474(17) 0.10221(10) 0.0332(5) Uani 1 1 d . . .
C6 C 0.9956(3) -0.0004(2) 0.07809(13) 0.0474(7) Uani 1 1 d . . .
H6 H 0.9197 -0.0166 0.0714 0.057 Uiso 1 1 calc R . .
C7 C 1.0799(3) -0.0622(2) 0.06377(15) 0.0597(9) Uani 1 1 d . . .
H7 H 1.0600 -0.1193 0.0476 0.072 Uiso 1 1 calc R . .
C8 C 1.1926(3) -0.0392(2) 0.07354(13) 0.0545(8) Uani 1 1 d . . .
H8 H 1.2488 -0.0806 0.0641 0.065 Uiso 1 1 calc R . .
C9 C 1.2213(3) 0.0456(2) 0.09733(12) 0.0514(8) Uani 1 1 d . . .
H9 H 1.2973 0.0616 0.1036 0.062 Uiso 1 1 calc R . .
C10 C 1.1378(2) 0.1073(2) 0.11205(11) 0.0409(6) Uani 1 1 d . . .
H10 H 1.1581 0.1641 0.1286 0.049 Uiso 1 1 calc R . .
C11 C 0.65470(19) 0.30191(17) 0.18539(9) 0.0279(5) Uani 1 1 d . . .
C12 C 0.6659(2) 0.39753(16) 0.20106(9) 0.0280(5) Uani 1 1 d . . .
C13 C 0.5864(2) 0.43988(18) 0.23625(10) 0.0328(5) Uani 1 1 d . . .
C14 C 0.4993(2) 0.3856(2) 0.25806(11) 0.0378(6) Uani 1 1 d . . .
H14 H 0.4471 0.4124 0.2816 0.045 Uiso 1 1 calc R . .
C15 C 0.4917(2) 0.2940(2) 0.24460(11) 0.0380(6) Uani 1 1 d . . .
H15 H 0.4346 0.2586 0.2596 0.046 Uiso 1 1 calc R . .
C16 C 0.5688(2) 0.25160(18) 0.20831(10) 0.0324(5) Uani 1 1 d . . .
H16 H 0.5616 0.1889 0.1998 0.039 Uiso 1 1 calc R . .
C17 C 0.6012(2) 0.53555(19) 0.24814(11) 0.0385(6) Uani 1 1 d . . .
H17 H 0.5508 0.5663 0.2708 0.046 Uiso 1 1 calc R . .
C18 C 0.6884(2) 0.58200(19) 0.22652(11) 0.0390(6) Uani 1 1 d . . .
H18 H 0.6963 0.6452 0.2333 0.047 Uiso 1 1 calc R . .
C19 C 0.7681(2) 0.53469(17) 0.19344(10) 0.0325(5) Uani 1 1 d . . .
C20 C 0.8651(2) 0.58538(18) 0.16981(11) 0.0388(6) Uani 1 1 d . . .
H20A H 0.9077 0.5439 0.1471 0.058 Uiso 1 1 calc R . .
H20B H 0.9132 0.6094 0.2013 0.058 Uiso 1 1 calc R . .
H20C H 0.8368 0.6356 0.1458 0.058 Uiso 1 1 calc R . .
C21 C 1.0700(2) 0.38011(16) 0.09310(10) 0.0313(5) Uani 1 1 d . . .
C22 C 1.1406(2) 0.36942(18) 0.04594(11) 0.0395(6) Uani 1 1 d . . .
C23 C 1.0849(3) 0.3700(2) -0.01008(12) 0.0492(8) Uani 1 1 d . . .
H23 H 1.1270 0.3646 -0.0427 0.059 Uiso 1 1 calc R . .
C24 C 0.9706(3) 0.3783(2) -0.01667(11) 0.0476(7) Uani 1 1 d . . .
H24 H 0.9350 0.3805 -0.0537 0.057 Uiso 1 1 calc R . .
C25 C 0.9050(2) 0.38350(17) 0.03277(11) 0.0372(6) Uani 1 1 d . . .
C26 C 0.7789(2) 0.3908(2) 0.02552(12) 0.0441(7) Uani 1 1 d . . .
H26A H 0.7481 0.3933 0.0630 0.066 Uiso 1 1 calc R . .
H26B H 0.7491 0.3377 0.0047 0.066 Uiso 1 1 calc R . .
H26C H 0.7586 0.4459 0.0042 0.066 Uiso 1 1 calc R . .
C27 C 1.2583(3) 0.3590(2) 0.05687(13) 0.0467(7) Uani 1 1 d . . .
H27 H 1.3048 0.3518 0.0261 0.056 Uiso 1 1 calc R . .
C28 C 1.3039(3) 0.3593(2) 0.11226(13) 0.0469(7) Uani 1 1 d . . .
H28 H 1.3815 0.3503 0.1191 0.056 Uiso 1 1 calc R . .
C29 C 1.2364(2) 0.37284(19) 0.15949(12) 0.0394(6) Uani 1 1 d . . .
H29 H 1.2699 0.3726 0.1970 0.047 Uiso 1 1 calc R . .
C30 C 1.1209(2) 0.38650(17) 0.15099(10) 0.0315(5) Uani 1 1 d . . .
C31 C 1.0613(2) 0.44815(16) 0.24233(10) 0.0295(5) Uani 1 1 d . . .
C32 C 1.1513(2) 0.52504(19) 0.24461(11) 0.0380(6) Uani 1 1 d . . .
C33 C 0.9975(2) 0.44200(17) 0.29107(10) 0.0311(5) Uani 1 1 d . . .
H33 H 1.0103 0.4859 0.3202 0.037 Uiso 1 1 calc R . .
C34 C 0.9147(2) 0.37370(17) 0.29922(10) 0.0291(5) Uani 1 1 d . . .
C35 C 0.8612(2) 0.36728(17) 0.35628(10) 0.0308(5) Uani 1 1 d . . .
C36 C 0.9152(2) 0.39486(19) 0.40867(11) 0.0389(6) Uani 1 1 d . . .
H36 H 0.9874 0.4204 0.4092 0.047 Uiso 1 1 calc R . .
C37 C 0.8617(3) 0.3845(2) 0.46009(11) 0.0457(7) Uani 1 1 d . . .
H37 H 0.8988 0.4025 0.4950 0.055 Uiso 1 1 calc R . .
C38 C 0.7539(3) 0.34771(19) 0.45993(12) 0.0451(7) Uani 1 1 d . . .
H38 H 0.7181 0.3412 0.4945 0.054 Uiso 1 1 calc R . .
C39 C 0.6995(3) 0.32052(19) 0.40780(12) 0.0411(6) Uani 1 1 d . . .
H39 H 0.6267 0.2959 0.4074 0.049 Uiso 1 1 calc R . .
C40 C 0.7525(2) 0.32976(17) 0.35659(11) 0.0333(6) Uani 1 1 d . . .
H40 H 0.7155 0.3108 0.3219 0.040 Uiso 1 1 calc R . .
C41 C 0.7020(4) 0.2495(3) -0.1717(2) 0.0826(12) Uani 1 1 d . . .
H41A H 0.7723 0.2694 -0.1527 0.124 Uiso 1 1 calc R . .
H41B H 0.7084 0.2498 -0.2130 0.124 Uiso 1 1 calc R . .
H41C H 0.6847 0.1880 -0.1592 0.124 Uiso 1 1 calc R . .
C42 C 0.6096(3) 0.3137(3) -0.15649(18) 0.0731(10) Uani 1 1 d . . .
H42A H 0.6263 0.3760 -0.1689 0.088 Uiso 1 1 calc R . .
H42B H 0.5383 0.2945 -0.1759 0.088 Uiso 1 1 calc R . .
C43 C 0.4949(4) 0.3502(3) -0.0749(2) 0.0966(15) Uani 1 1 d . . .
H43A H 0.4306 0.3248 -0.0977 0.116 Uiso 1 1 calc R . .
H43B H 0.4885 0.3319 -0.0348 0.116 Uiso 1 1 calc R . .
C44 C 0.4920(5) 0.4476(3) -0.0787(2) 0.1055(17) Uani 1 1 d . . .
H44A H 0.4224 0.4700 -0.0645 0.158 Uiso 1 1 calc R . .
H44B H 0.4967 0.4660 -0.1185 0.158 Uiso 1 1 calc R . .
H44C H 0.5549 0.4731 -0.0558 0.158 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 N3 2.061(2) . ?
Zn1 N1 2.0624(19) . ?
Zn1 O1 2.0862(16) . ?
Zn1 O2 2.0949(15) . ?
Zn1 N2 2.2365(19) . ?
Zn1 N4 2.2472(19) . ?
F1 C2 1.337(3) . ?
F2 C2 1.347(3) . ?
F3 C2 1.343(3) . ?
F4 C32 1.347(3) . ?
F5 C32 1.336(3) . ?
F6 C32 1.340(3) . ?
O2 C34 1.263(3) . ?
O1 C4 1.258(3) . ?
O3 C42 1.397(5) . ?
O3 C43 1.493(6) . ?
N1 C1 1.328(3) . ?
N1 C11 1.402(3) . ?
N2 C19 1.328(3) . ?
N2 C12 1.375(3) . ?
N4 C25 1.331(3) . ?
N4 C21 1.369(3) . ?
N3 C31 1.322(3) . ?
N3 C30 1.401(3) . ?
C1 C3 1.394(3) . ?
C1 C2 1.531(3) . ?
C3 C4 1.414(4) . ?
C4 C5 1.500(3) . ?
C5 C6 1.383(4) . ?
C5 C10 1.393(4) . ?
C6 C7 1.393(4) . ?
C7 C8 1.379(5) . ?
C8 C9 1.376(5) . ?
C9 C10 1.389(4) . ?
C11 C16 1.380(3) . ?
C11 C12 1.432(3) . ?
C12 C13 1.417(3) . ?
C13 C14 1.412(4) . ?
C13 C17 1.418(4) . ?
C14 C15 1.361(4) . ?
C15 C16 1.414(3) . ?
C17 C18 1.350(4) . ?
C18 C19 1.424(4) . ?
C19 C20 1.491(4) . ?
C21 C22 1.419(3) . ?
C21 C30 1.434(3) . ?
C22 C27 1.407(4) . ?
C22 C23 1.414(4) . ?
C23 C24 1.356(4) . ?
C24 C25 1.420(4) . ?
C25 C26 1.493(4) . ?
C27 C28 1.356(4) . ?
C28 C29 1.403(4) . ?
C29 C30 1.382(4) . ?
C31 C33 1.395(3) . ?
C31 C32 1.537(3) . ?
C33 C34 1.411(3) . ?
C34 C35 1.497(3) . ?
C35 C36 1.390(4) . ?
C35 C40 1.396(4) . ?
C36 C37 1.385(4) . ?
C37 C38 1.382(4) . ?
C38 C39 1.386(4) . ?
C39 C40 1.377(3) . ?
C41 C42 1.490(5) . ?
C43 C44 1.410(6) . ?

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 173.19(8) . . ?
N3 Zn1 O1 90.37(7) . . ?
N1 Zn1 O1 84.84(7) . . ?
N3 Zn1 O2 84.58(7) . . ?
N1 Zn1 O2 90.96(7) . . ?
O1 Zn1 O2 94.40(6) . . ?
N3 Zn1 N2 107.72(8) . . ?
N1 Zn1 N2 76.91(7) . . ?
O1 Zn1 N2 161.72(7) . . ?
O2 Zn1 N2 84.92(7) . . ?
N3 Zn1 N4 76.70(7) . . ?
N1 Zn1 N4 107.79(7) . . ?
O1 Zn1 N4 87.07(7) . . ?
O2 Zn1 N4 161.24(7) . . ?
N2 Zn1 N4 99.44(7) . . ?
C34 O2 Zn1 124.02(15) . . ?
C4 O1 Zn1 124.64(15) . . ?
C42 O3 C43 115.4(3) . . ?
C1 N1 C11 127.2(2) . . ?
C1 N1 Zn1 121.69(15) . . ?
C11 N1 Zn1 110.77(15) . . ?
C19 N2 C12 119.4(2) . . ?
C19 N2 Zn1 129.56(17) . . ?
C12 N2 Zn1 105.20(14) . . ?
C25 N4 C21 119.1(2) . . ?
C25 N4 Zn1 131.12(18) . . ?
C21 N4 Zn1 105.75(15) . . ?
C31 N3 C30 126.4(2) . . ?
C31 N3 Zn1 122.03(16) . . ?
C30 N3 Zn1 110.93(15) . . ?
N1 C1 C3 124.8(2) . . ?
N1 C1 C2 120.1(2) . . ?
C3 C1 C2 115.0(2) . . ?
F1 C2 F3 105.9(2) . . ?
F1 C2 F2 106.6(2) . . ?
F3 C2 F2 105.8(2) . . ?
F1 C2 C1 112.7(2) . . ?
F3 C2 C1 111.9(2) . . ?
F2 C2 C1 113.5(2) . . ?
C1 C3 C4 124.6(2) . . ?
O1 C4 C3 124.0(2) . . ?
O1 C4 C5 115.8(2) . . ?
C3 C4 C5 120.2(2) . . ?
C6 C5 C10 118.7(2) . . ?
C6 C5 C4 122.8(2) . . ?
C10 C5 C4 118.5(2) . . ?
C5 C6 C7 120.6(3) . . ?
C8 C7 C6 120.3(3) . . ?
C9 C8 C7 119.5(3) . . ?
C8 C9 C10 120.5(3) . . ?
C9 C10 C5 120.4(3) . . ?
C16 C11 N1 125.7(2) . . ?
C16 C11 C12 118.1(2) . . ?
N1 C11 C12 115.7(2) . . ?
N2 C12 C13 122.0(2) . . ?
N2 C12 C11 117.5(2) . . ?
C13 C12 C11 120.5(2) . . ?
C14 C13 C17 123.8(2) . . ?
C14 C13 C12 119.2(2) . . ?
C17 C13 C12 117.0(2) . . ?
C15 C14 C13 119.9(2) . . ?
C14 C15 C16 121.4(2) . . ?
C11 C16 C15 120.9(2) . . ?
C18 C17 C13 120.1(2) . . ?
C17 C18 C19 120.3(2) . . ?
N2 C19 C18 121.1(2) . . ?
N2 C19 C20 118.3(2) . . ?
C18 C19 C20 120.6(2) . . ?
N4 C21 C22 123.1(2) . . ?
N4 C21 C30 117.8(2) . . ?
C22 C21 C30 119.2(2) . . ?
C27 C22 C21 119.7(3) . . ?
C27 C22 C23 124.4(2) . . ?
C21 C22 C23 115.9(3) . . ?
C24 C23 C22 120.6(2) . . ?
C23 C24 C25 120.3(3) . . ?
N4 C25 C24 120.9(3) . . ?
N4 C25 C26 118.8(2) . . ?
C24 C25 C26 120.3(2) . . ?
C28 C27 C22 120.0(2) . . ?
C27 C28 C29 121.3(3) . . ?
C30 C29 C28 120.9(3) . . ?
C29 C30 N3 125.5(2) . . ?
C29 C30 C21 118.6(2) . . ?
N3 C30 C21 115.6(2) . . ?
N3 C31 C33 124.9(2) . . ?
N3 C31 C32 119.8(2) . . ?
C33 C31 C32 115.2(2) . . ?
F5 C32 F6 107.7(2) . . ?
F5 C32 F4 106.1(2) . . ?
F6 C32 F4 105.7(2) . . ?
F5 C32 C31 112.1(2) . . ?
F6 C32 C31 113.2(2) . . ?
F4 C32 C31 111.6(2) . . ?
C31 C33 C34 124.5(2) . . ?
O2 C34 C33 124.2(2) . . ?
O2 C34 C35 116.2(2) . . ?
C33 C34 C35 119.6(2) . . ?
C36 C35 C40 118.7(2) . . ?
C36 C35 C34 123.4(2) . . ?
C40 C35 C34 117.8(2) . . ?
C37 C36 C35 120.3(3) . . ?
C36 C37 C38 120.5(3) . . ?
C37 C38 C39 119.4(2) . . ?
C40 C39 C38 120.3(3) . . ?
C39 C40 C35 120.6(2) . . ?
O3 C42 C41 108.3(4) . . ?
C44 C43 O3 111.9(4) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.783
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 1005750'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_frit17

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H14 F12 N4 O2 Zn'
_chemical_formula_sum            'C28 H14 F12 N4 O2 Zn'
_chemical_formula_weight         731.80

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   10.944(3)
_cell_length_b                   15.110(4)
_cell_length_c                   17.767(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.388(11)
_cell_angle_gamma                90.00
_cell_volume                     2846.0(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8238
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      26.19

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1456
_exptl_absorpt_coefficient_mu    0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7922
_exptl_absorpt_correction_T_max  0.8673
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21545
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         26.34
_reflns_number_total             5767
_reflns_number_gt                4910
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0213P)²+1.9835P] where P=(Fo²+2Fc²)/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         5767
_refine_ls_number_parameters     424
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0651
_refine_ls_wR_factor_gt          0.0614
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.669280(18) 0.363501(13) 0.719201(11) 0.01067(6) Uani 1 1 d . . .
F1 F 0.90438(13) 0.16543(10) 0.63090(7) 0.0407(4) Uani 1 1 d . . .
F2 F 0.86420(12) 0.07325(8) 0.71409(9) 0.0384(3) Uani 1 1 d . . .
F3 F 1.04555(11) 0.13652(8) 0.73599(7) 0.0301(3) Uani 1 1 d . . .
F4 F 1.12903(10) 0.37042(8) 0.89606(7) 0.0280(3) Uani 1 1 d . . .
F5 F 1.02617(11) 0.34085(9) 0.98135(6) 0.0305(3) Uani 1 1 d . . .
F6 F 1.00292(10) 0.46808(8) 0.92238(7) 0.0271(3) Uani 1 1 d . . .
F7 F 0.36110(13) 0.37510(12) 0.84413(8) 0.0527(4) Uani 1 1 d . . .
F8 F 0.31770(14) 0.24100(11) 0.81018(9) 0.0509(4) Uani 1 1 d . . .
F9 F 0.20056(11) 0.34533(11) 0.74983(8) 0.0449(4) Uani 1 1 d . . .
F10 F 0.23865(10) 0.43031(8) 0.51743(7) 0.0260(3) Uani 1 1 d . . .
F11 F 0.29055(11) 0.30837(8) 0.47049(7) 0.0281(3) Uani 1 1 d . . .
F12 F 0.39889(10) 0.42845(8) 0.46841(6) 0.0235(3) Uani 1 1 d . . .
O1 O 0.74998(11) 0.23806(8) 0.71677(7) 0.0145(3) Uani 1 1 d . . .
O2 O 0.52134(11) 0.31277(8) 0.76074(7) 0.0143(3) Uani 1 1 d . . .
N1 N 0.79397(13) 0.37330(10) 0.83268(8) 0.0118(3) Uani 1 1 d . . .
N2 N 0.61867(14) 0.48913(10) 0.75879(8) 0.0136(3) Uani 1 1 d . . .
N3 N 0.54471(13) 0.34538(9) 0.60609(8) 0.0116(3) Uani 1 1 d . . .
N4 N 0.78190(13) 0.40788(10) 0.64387(8) 0.0126(3) Uani 1 1 d . . .
C1 C 0.92199(18) 0.15060(13) 0.70707(11) 0.0202(4) Uani 1 1 d . . .
C2 C 0.86732(16) 0.22657(11) 0.74559(10) 0.0128(4) Uani 1 1 d . . .
C3 C 0.94823(16) 0.27278(12) 0.80491(10) 0.0138(4) Uani 1 1 d . . .
H3A H 1.0350 0.2570 0.8177 0.017 Uiso 1 1 calc R . .
C4 C 0.90991(16) 0.34231(12) 0.84786(10) 0.0127(4) Uani 1 1 d . . .
C5 C 1.01693(17) 0.38117(13) 0.91265(11) 0.0196(4) Uani 1 1 d . . .
C6 C 0.74308(16) 0.43119(12) 0.87970(10) 0.0128(4) Uani 1 1 d . . .
C7 C 0.76451(16) 0.42639(12) 0.95951(10) 0.0148(4) Uani 1 1 d . . .
H7A H 0.8222 0.3838 0.9874 0.018 Uiso 1 1 calc R . .
C8 C 0.70191(17) 0.48386(13) 1.00031(11) 0.0169(4) Uani 1 1 d . . .
H8A H 0.7188 0.4796 1.0553 0.020 Uiso 1 1 calc R . .
C9 C 0.61733(17) 0.54571(12) 0.96210(11) 0.0175(4) Uani 1 1 d . . .
H9A H 0.5790 0.5855 0.9907 0.021 Uiso 1 1 calc R . .
C10 C 0.58709(17) 0.55024(12) 0.87963(11) 0.0159(4) Uani 1 1 d . . .
C11 C 0.49441(18) 0.60772(13) 0.83549(12) 0.0200(4) Uani 1 1 d . . .
H11A H 0.4515 0.6481 0.8609 0.024 Uiso 1 1 calc R . .
C12 C 0.46670(19) 0.60502(13) 0.75591(12) 0.0213(4) Uani 1 1 d . . .
H12A H 0.4053 0.6437 0.7257 0.026 Uiso 1 1 calc R . .
C13 C 0.53070(18) 0.54407(12) 0.71984(11) 0.0179(4) Uani 1 1 d . . .
H13A H 0.5100 0.5420 0.6647 0.021 Uiso 1 1 calc R . .
C14 C 0.64878(16) 0.49182(12) 0.83849(10) 0.0128(4) Uani 1 1 d . . .
C15 C 0.31957(18) 0.32322(16) 0.78243(12) 0.0264(5) Uani 1 1 d . . .
C16 C 0.40750(16) 0.32898(12) 0.72727(11) 0.0153(4) Uani 1 1 d . . .
C17 C 0.35433(17) 0.35181(12) 0.65050(11) 0.0159(4) Uani 1 1 d . . .
H17A H 0.2666 0.3647 0.6360 0.019 Uiso 1 1 calc R . .
C18 C 0.42195(16) 0.35715(11) 0.59238(10) 0.0134(4) Uani 1 1 d . . .
C19 C 0.33807(17) 0.38078(13) 0.51141(11) 0.0175(4) Uani 1 1 d . . .
C20 C 0.61527(16) 0.33594(11) 0.54987(10) 0.0124(4) Uani 1 1 d . . .
C21 C 0.57785(17) 0.28937(12) 0.48101(10) 0.0158(4) Uani 1 1 d . . .
H21A H 0.4976 0.2614 0.4681 0.019 Uiso 1 1 calc R . .
C22 C 0.65720(18) 0.28285(13) 0.42966(11) 0.0190(4) Uani 1 1 d . . .
H22A H 0.6291 0.2514 0.3822 0.023 Uiso 1 1 calc R . .
C23 C 0.77456(18) 0.32137(13) 0.44729(11) 0.0191(4) Uani 1 1 d . . .
H23A H 0.8253 0.3189 0.4110 0.023 Uiso 1 1 calc R . .
C24 C 0.82007(17) 0.36484(12) 0.51953(10) 0.0155(4) Uani 1 1 d . . .
C25 C 0.94208(17) 0.40291(13) 0.54372(11) 0.0192(4) Uani 1 1 d . . .
H25A H 0.9977 0.4008 0.5103 0.023 Uiso 1 1 calc R . .
C26 C 0.97992(17) 0.44264(13) 0.61499(11) 0.0201(4) Uani 1 1 d . . .
H26A H 1.0604 0.4700 0.6309 0.024 Uiso 1 1 calc R . .
C27 C 0.89677(17) 0.44216(12) 0.66436(11) 0.0166(4) Uani 1 1 d . . .
H27A H 0.9245 0.4676 0.7146 0.020 Uiso 1 1 calc R . .
C28 C 0.74082(16) 0.37073(11) 0.57143(10) 0.0119(3) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O2 2.0851(12) . ?
Zn1 O1 2.0961(13) . ?
Zn1 N4 2.1401(15) . ?
Zn1 N1 2.1405(15) . ?
Zn1 N2 2.1445(15) . ?
Zn1 N3 2.1472(15) . ?
F1 C1 1.338(2) . ?
F2 C1 1.349(2) . ?
F3 C1 1.339(2) . ?
F4 C5 1.341(2) . ?
F5 C5 1.345(2) . ?
F6 C5 1.338(2) . ?
F7 C15 1.332(3) . ?
F8 C15 1.339(3) . ?
F9 C15 1.330(2) . ?
F10 C19 1.347(2) . ?
F11 C19 1.345(2) . ?
F12 C19 1.341(2) . ?
O1 C2 1.271(2) . ?
O2 C16 1.264(2) . ?
N1 C4 1.316(2) . ?
N1 C6 1.416(2) . ?
N2 C13 1.328(2) . ?
N2 C14 1.372(2) . ?
N3 C18 1.317(2) . ?
N3 C20 1.413(2) . ?
N4 C27 1.324(2) . ?
N4 C28 1.373(2) . ?
C1 C2 1.532(3) . ?
C2 C3 1.385(3) . ?
C3 C4 1.422(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.540(3) . ?
C6 C7 1.380(3) . ?
C6 C14 1.437(3) . ?
C7 C8 1.413(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.371(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.421(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.415(3) . ?
C10 C14 1.419(2) . ?
C11 C12 1.371(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.404(3) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C15 C16 1.537(3) . ?
C16 C17 1.387(3) . ?
C17 C18 1.414(3) . ?
C17 H17A 0.9500 . ?
C18 C19 1.544(2) . ?
C20 C21 1.382(3) . ?
C20 C28 1.432(2) . ?
C21 C22 1.411(3) . ?
C21 H21A 0.9500 . ?
C22 C23 1.374(3) . ?
C22 H22A 0.9500 . ?
C23 C24 1.417(3) . ?
C23 H23A 0.9500 . ?
C24 C28 1.417(2) . ?
C24 C25 1.419(3) . ?
C25 C26 1.369(3) . ?
C25 H25A 0.9500 . ?
C26 C27 1.412(3) . ?
C26 H26A 0.9500 . ?
C27 H27A 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
O2 Zn1 O1 92.47(5) . . ?
O2 Zn1 N4 162.77(5) . . ?
O1 Zn1 N4 87.67(5) . . ?
O2 Zn1 N1 93.52(5) . . ?
O1 Zn1 N1 84.76(5) . . ?
N4 Zn1 N1 103.65(6) . . ?
O2 Zn1 N2 85.57(5) . . ?
O1 Zn1 N2 162.13(5) . . ?
N4 Zn1 N2 99.41(6) . . ?
N1 Zn1 N2 77.64(6) . . ?
O2 Zn1 N3 85.19(5) . . ?
O1 Zn1 N3 92.19(5) . . ?
N4 Zn1 N3 77.59(6) . . ?
N1 Zn1 N3 176.64(6) . . ?
N2 Zn1 N3 105.32(6) . . ?
C2 O1 Zn1 120.27(11) . . ?
C16 O2 Zn1 121.57(11) . . ?
C4 N1 C6 126.83(15) . . ?
C4 N1 Zn1 121.66(12) . . ?
C6 N1 Zn1 110.27(11) . . ?
C13 N2 C14 118.44(15) . . ?
C13 N2 Zn1 126.53(13) . . ?
C14 N2 Zn1 110.45(11) . . ?
C18 N3 C20 126.48(15) . . ?
C18 N3 Zn1 122.50(12) . . ?
C20 N3 Zn1 110.06(11) . . ?
C27 N4 C28 119.00(15) . . ?
C27 N4 Zn1 127.27(12) . . ?
C28 N4 Zn1 110.65(11) . . ?
F1 C1 F3 107.03(16) . . ?
F1 C1 F2 106.59(16) . . ?
F3 C1 F2 106.19(15) . . ?
F1 C1 C2 110.63(15) . . ?
F3 C1 C2 114.64(15) . . ?
F2 C1 C2 111.32(16) . . ?
O1 C2 C3 128.96(16) . . ?
O1 C2 C1 112.96(15) . . ?
C3 C2 C1 118.09(16) . . ?
C2 C3 C4 124.26(16) . . ?
C2 C3 H3A 117.9 . . ?
C4 C3 H3A 117.9 . . ?
N1 C4 C3 123.43(16) . . ?
N1 C4 C5 122.21(16) . . ?
C3 C4 C5 114.33(15) . . ?
F6 C5 F4 106.72(15) . . ?
F6 C5 F5 108.21(15) . . ?
F4 C5 F5 106.14(15) . . ?
F6 C5 C4 112.35(15) . . ?
F4 C5 C4 110.91(15) . . ?
F5 C5 C4 112.17(16) . . ?
C7 C6 N1 125.62(16) . . ?
C7 C6 C14 118.30(16) . . ?
N1 C6 C14 115.54(15) . . ?
C6 C7 C8 120.97(17) . . ?
C6 C7 H7A 119.5 . . ?
C8 C7 H7A 119.5 . . ?
C9 C8 C7 121.26(17) . . ?
C9 C8 H8A 119.4 . . ?
C7 C8 H8A 119.4 . . ?
C8 C9 C10 119.93(17) . . ?
C8 C9 H9A 120.0 . . ?
C10 C9 H9A 120.0 . . ?
C11 C10 C14 117.61(17) . . ?
C11 C10 C9 123.50(17) . . ?
C14 C10 C9 118.84(17) . . ?
C12 C11 C10 119.84(18) . . ?
C12 C11 H11A 120.1 . . ?
C10 C11 H11A 120.1 . . ?
C11 C12 C13 118.85(18) . . ?
C11 C12 H12A 120.6 . . ?
C13 C12 H12A 120.6 . . ?
N2 C13 C12 123.46(18) . . ?
N2 C13 H13A 118.3 . . ?
C12 C13 H13A 118.3 . . ?
N2 C14 C10 121.79(16) . . ?
N2 C14 C6 117.70(15) . . ?
C10 C14 C6 120.49(16) . . ?
F9 C15 F7 107.91(18) . . ?
F9 C15 F8 106.90(17) . . ?
F7 C15 F8 106.04(18) . . ?
F9 C15 C16 114.12(16) . . ?
F7 C15 C16 110.59(17) . . ?
F8 C15 C16 110.90(18) . . ?
O2 C16 C17 129.38(16) . . ?
O2 C16 C15 112.91(16) . . ?
C17 C16 C15 117.71(16) . . ?
C16 C17 C18 124.36(17) . . ?
C16 C17 H17A 117.8 . . ?
C18 C17 H17A 117.8 . . ?
N3 C18 C17 123.53(16) . . ?
N3 C18 C19 123.15(16) . . ?
C17 C18 C19 113.30(15) . . ?
F11 C19 F12 108.00(15) . . ?
F11 C19 F10 106.47(15) . . ?
F12 C19 F10 105.79(15) . . ?
F11 C19 C18 112.09(15) . . ?
F12 C19 C18 113.00(15) . . ?
F10 C19 C18 111.08(15) . . ?
C21 C20 N3 125.67(16) . . ?
C21 C20 C28 118.51(16) . . ?
N3 C20 C28 115.50(15) . . ?
C20 C21 C22 120.89(17) . . ?
C20 C21 H21A 119.6 . . ?
C22 C21 H21A 119.6 . . ?
C23 C22 C21 120.93(18) . . ?
C23 C22 H22A 119.5 . . ?
C21 C22 H22A 119.5 . . ?
C22 C23 C24 120.08(17) . . ?
C22 C23 H23A 120.0 . . ?
C24 C23 H23A 120.0 . . ?
C28 C24 C25 117.36(17) . . ?
C28 C24 C23 118.95(17) . . ?
C25 C24 C23 123.68(17) . . ?
C26 C25 C24 120.23(17) . . ?
C26 C25 H25A 119.9 . . ?
C24 C25 H25A 119.9 . . ?
C25 C26 C27 118.60(17) . . ?
C25 C26 H26A 120.7 . . ?
C27 C26 H26A 120.7 . . ?
N4 C27 C26 123.06(18) . . ?
N4 C27 H27A 118.5 . . ?
C26 C27 H27A 118.5 . . ?
N4 C28 C24 121.65(16) . . ?
N4 C28 C20 118.02(15) . . ?
C24 C28 C20 120.32(16) . . ?

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
O2 Zn1 O1 C2 -132.35(13) . . . . ?
N4 Zn1 O1 C2 64.90(13) . . . . ?
N1 Zn1 O1 C2 -39.04(13) . . . . ?
N2 Zn1 O1 C2 -49.1(2) . . . . ?
N3 Zn1 O1 C2 142.38(13) . . . . ?
O1 Zn1 O2 C16 -127.16(13) . . . . ?
N4 Zn1 O2 C16 -37.1(2) . . . . ?
N1 Zn1 O2 C16 147.94(14) . . . . ?
N2 Zn1 O2 C16 70.64(14) . . . . ?
N3 Zn1 O2 C16 -35.17(13) . . . . ?
O2 Zn1 N1 C4 131.09(14) . . . . ?
O1 Zn1 N1 C4 38.93(13) . . . . ?
N4 Zn1 N1 C4 -47.39(14) . . . . ?
N2 Zn1 N1 C4 -144.23(14) . . . . ?
N3 Zn1 N1 C4 63.8(10) . . . . ?
O2 Zn1 N1 C6 -60.79(11) . . . . ?
O1 Zn1 N1 C6 -152.95(11) . . . . ?
N4 Zn1 N1 C6 120.73(11) . . . . ?
N2 Zn1 N1 C6 23.89(11) . . . . ?
N3 Zn1 N1 C6 -128.1(9) . . . . ?
O2 Zn1 N2 C13 -85.28(15) . . . . ?
O1 Zn1 N2 C13 -169.57(15) . . . . ?
N4 Zn1 N2 C13 78.09(16) . . . . ?
N1 Zn1 N2 C13 -179.87(16) . . . . ?
N3 Zn1 N2 C13 -1.51(16) . . . . ?
O2 Zn1 N2 C14 70.05(12) . . . . ?
O1 Zn1 N2 C14 -14.2(2) . . . . ?
N4 Zn1 N2 C14 -126.58(12) . . . . ?
N1 Zn1 N2 C14 -24.54(11) . . . . ?
N3 Zn1 N2 C14 153.82(11) . . . . ?
O2 Zn1 N3 C18 35.26(13) . . . . ?
O1 Zn1 N3 C18 127.55(13) . . . . ?
N4 Zn1 N3 C18 -145.32(14) . . . . ?
N1 Zn1 N3 C18 102.7(9) . . . . ?
N2 Zn1 N3 C18 -48.81(14) . . . . ?
O2 Zn1 N3 C20 -155.31(11) . . . . ?
O1 Zn1 N3 C20 -63.01(11) . . . . ?
N4 Zn1 N3 C20 24.12(11) . . . . ?
N1 Zn1 N3 C20 -87.8(9) . . . . ?
N2 Zn1 N3 C20 120.63(11) . . . . ?
O2 Zn1 N4 C27 178.61(15) . . . . ?
O1 Zn1 N4 C27 -90.57(15) . . . . ?
N1 Zn1 N4 C27 -6.53(16) . . . . ?
N2 Zn1 N4 C27 72.93(16) . . . . ?
N3 Zn1 N4 C27 176.68(16) . . . . ?
O2 Zn1 N4 C28 -21.7(2) . . . . ?
O1 Zn1 N4 C28 69.12(11) . . . . ?
N1 Zn1 N4 C28 153.16(11) . . . . ?
N2 Zn1 N4 C28 -127.38(11) . . . . ?
N3 Zn1 N4 C28 -23.63(11) . . . . ?
Zn1 O1 C2 C3 27.5(2) . . . . ?
Zn1 O1 C2 C1 -152.19(12) . . . . ?
F1 C1 C2 O1 58.9(2) . . . . ?
F3 C1 C2 O1 -179.98(15) . . . . ?
F2 C1 C2 O1 -59.4(2) . . . . ?
F1 C1 C2 C3 -120.87(18) . . . . ?
F3 C1 C2 C3 0.3(2) . . . . ?
F2 C1 C2 C3 120.81(18) . . . . ?
O1 C2 C3 C4 2.9(3) . . . . ?
C1 C2 C3 C4 -177.42(17) . . . . ?
C6 N1 C4 C3 168.61(17) . . . . ?
Zn1 N1 C4 C3 -25.3(2) . . . . ?
C6 N1 C4 C5 -13.5(3) . . . . ?
Zn1 N1 C4 C5 152.55(13) . . . . ?
C2 C3 C4 N1 -3.9(3) . . . . ?
C2 C3 C4 C5 178.08(17) . . . . ?
N1 C4 C5 F6 -32.4(2) . . . . ?
C3 C4 C5 F6 145.72(16) . . . . ?
N1 C4 C5 F4 -151.71(17) . . . . ?
C3 C4 C5 F4 26.4(2) . . . . ?
N1 C4 C5 F5 89.8(2) . . . . ?
C3 C4 C5 F5 -92.12(18) . . . . ?
C4 N1 C6 C7 -41.5(3) . . . . ?
Zn1 N1 C6 C7 151.16(15) . . . . ?
C4 N1 C6 C14 147.13(17) . . . . ?
Zn1 N1 C6 C14 -20.22(18) . . . . ?
N1 C6 C7 C8 -175.54(16) . . . . ?
C14 C6 C7 C8 -4.4(3) . . . . ?
C6 C7 C8 C9 0.5(3) . . . . ?
C7 C8 C9 C10 2.8(3) . . . . ?
C8 C9 C10 C11 175.37(18) . . . . ?
C8 C9 C10 C14 -2.0(3) . . . . ?
C14 C10 C11 C12 0.5(3) . . . . ?
C9 C10 C11 C12 -176.90(18) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
C14 N2 C13 C12 0.1(3) . . . . ?
Zn1 N2 C13 C12 153.65(15) . . . . ?
C11 C12 C13 N2 -0.9(3) . . . . ?
C13 N2 C14 C10 1.1(3) . . . . ?
Zn1 N2 C14 C10 -156.45(14) . . . . ?
C13 N2 C14 C6 179.27(16) . . . . ?
Zn1 N2 C14 C6 21.69(19) . . . . ?
C11 C10 C14 N2 -1.4(3) . . . . ?
C9 C10 C14 N2 176.11(16) . . . . ?
C11 C10 C14 C6 -179.48(16) . . . . ?
C9 C10 C14 C6 -2.0(3) . . . . ?
C7 C6 C14 N2 -173.06(16) . . . . ?
N1 C6 C14 N2 -1.0(2) . . . . ?
C7 C6 C14 C10 5.1(3) . . . . ?
N1 C6 C14 C10 177.15(15) . . . . ?
Zn1 O2 C16 C17 24.6(3) . . . . ?
Zn1 O2 C16 C15 -154.26(13) . . . . ?
F9 C15 C16 O2 176.05(18) . . . . ?
F7 C15 C16 O2 54.2(2) . . . . ?
F8 C15 C16 O2 -63.2(2) . . . . ?
F9 C15 C16 C17 -3.0(3) . . . . ?
F7 C15 C16 C17 -124.8(2) . . . . ?
F8 C15 C16 C17 117.83(19) . . . . ?
O2 C16 C17 C18 3.2(3) . . . . ?
C15 C16 C17 C18 -177.96(18) . . . . ?
C20 N3 C18 C17 169.34(17) . . . . ?
Zn1 N3 C18 C17 -23.0(2) . . . . ?
C20 N3 C18 C19 -12.4(3) . . . . ?
Zn1 N3 C18 C19 155.21(13) . . . . ?
C16 C17 C18 N3 -3.7(3) . . . . ?
C16 C17 C18 C19 177.93(17) . . . . ?
N3 C18 C19 F11 91.8(2) . . . . ?
C17 C18 C19 F11 -89.81(19) . . . . ?
N3 C18 C19 F12 -30.5(2) . . . . ?
C17 C18 C19 F12 147.87(16) . . . . ?
N3 C18 C19 F10 -149.24(16) . . . . ?
C17 C18 C19 F10 29.2(2) . . . . ?
C18 N3 C20 C21 -39.2(3) . . . . ?
Zn1 N3 C20 C21 151.85(15) . . . . ?
C18 N3 C20 C28 147.40(17) . . . . ?
Zn1 N3 C20 C28 -21.51(18) . . . . ?
N3 C20 C21 C22 -178.76(17) . . . . ?
C28 C20 C21 C22 -5.6(3) . . . . ?
C20 C21 C22 C23 1.1(3) . . . . ?
C21 C22 C23 C24 3.0(3) . . . . ?
C22 C23 C24 C28 -2.4(3) . . . . ?
C22 C23 C24 C25 177.15(18) . . . . ?
C28 C24 C25 C26 0.6(3) . . . . ?
C23 C24 C25 C26 -178.98(18) . . . . ?
C24 C25 C26 C27 2.1(3) . . . . ?
C28 N4 C27 C26 0.1(3) . . . . ?
Zn1 N4 C27 C26 158.34(14) . . . . ?
C25 C26 C27 N4 -2.5(3) . . . . ?
C27 N4 C28 C24 2.7(2) . . . . ?
Zn1 N4 C28 C24 -158.86(13) . . . . ?
C27 N4 C28 C20 -178.57(16) . . . . ?
Zn1 N4 C28 C20 19.84(18) . . . . ?
C25 C24 C28 N4 -3.1(3) . . . . ?
C23 C24 C28 N4 176.52(16) . . . . ?
C25 C24 C28 C20 178.25(16) . . . . ?
C23 C24 C28 C20 -2.1(3) . . . . ?
C21 C20 C28 N4 -172.62(16) . . . . ?
N3 C20 C28 N4 1.2(2) . . . . ?
C21 C20 C28 C24 6.1(2) . . . . ?
N3 C20 C28 C24 179.97(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.055
_database_code_depnum_ccdc_archive 'CCDC 1005751'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_frit13

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H18 F12 N4 O2 Zn'
_chemical_formula_weight         759.85

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   10.8018(4)
_cell_length_b                   16.7358(7)
_cell_length_c                   16.7518(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.1130(10)
_cell_angle_gamma                90.00
_cell_volume                     2949.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9886
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      26.40

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1520
_exptl_absorpt_coefficient_mu    0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7644
_exptl_absorpt_correction_T_max  0.8333
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            21113
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         26.41
_reflns_number_total             6007
_reflns_number_gt                5354
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0500P)²+3.0000P] where P=(Fo²+2Fc²)/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         6007
_refine_ls_number_parameters     443
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0893
_refine_ls_wR_factor_gt          0.0848
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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 0.391709(19) 0.864933(13) 0.241326(12) 0.01128(8) Uani 1 1 d . . .
F1 F 0.71513(13) 0.64177(8) 0.19305(8) 0.0294(3) Uani 1 1 d . . .
F2 F 0.56288(14) 0.59818(8) 0.24496(9) 0.0328(3) Uani 1 1 d . . .
F3 F 0.69962(14) 0.68088(10) 0.31225(8) 0.0360(3) Uani 1 1 d . . .
F4 F 0.64037(12) 0.83320(8) 0.00630(8) 0.0250(3) Uani 1 1 d . . .
F5 F 0.45103(13) 0.80245(8) -0.05769(7) 0.0258(3) Uani 1 1 d . . .
F6 F 0.49760(12) 0.92381(7) -0.01845(7) 0.0236(3) Uani 1 1 d . . .
F7 F -0.08359(12) 0.78870(9) 0.26861(8) 0.0317(3) Uani 1 1 d . . .
F8 F -0.06390(18) 0.8628(2) 0.17208(16) 0.1165(14) Uani 1 1 d . . .
F9 F -0.01451(18) 0.7396(2) 0.17188(16) 0.1131(13) Uani 1 1 d . . .
F10 F 0.37656(11) 0.92890(8) 0.51188(7) 0.0238(3) Uani 1 1 d . . .
F11 F 0.27375(13) 0.82233(9) 0.52962(7) 0.0311(3) Uani 1 1 d . . .
F12 F 0.17342(12) 0.92833(9) 0.48015(8) 0.0323(3) Uani 1 1 d . . .
O1 O 0.46647(13) 0.75029(8) 0.24365(8) 0.0150(3) Uani 1 1 d . . .
O2 O 0.20456(13) 0.81879(9) 0.21269(8) 0.0165(3) Uani 1 1 d . . .
N1 N 0.39484(15) 0.86322(9) 0.11395(9) 0.0117(3) Uani 1 1 d . . .
N2 N 0.32272(15) 0.98265(10) 0.20166(10) 0.0142(3) Uani 1 1 d . . .
N3 N 0.38037(15) 0.84684(10) 0.36487(9) 0.0130(3) Uani 1 1 d . . .
N4 N 0.58019(15) 0.90525(10) 0.31075(9) 0.0132(3) Uani 1 1 d . . .
C1 C 0.6318(2) 0.66337(13) 0.23723(13) 0.0206(4) Uani 1 1 d . . .
C2 C 0.54521(18) 0.73273(11) 0.20119(11) 0.0141(4) Uani 1 1 d . . .
C3 C 0.56243(18) 0.76626(12) 0.12909(12) 0.0151(4) Uani 1 1 d . . .
H3A H 0.6307 0.7472 0.1072 0.018 Uiso 1 1 calc R . .
C4 C 0.48417(18) 0.82745(11) 0.08598(11) 0.0131(4) Uani 1 1 d . . .
C5 C 0.51728(19) 0.84771(12) 0.00338(12) 0.0173(4) Uani 1 1 d . . .
C6 C 0.30552(18) 0.91834(12) 0.07078(12) 0.0140(4) Uani 1 1 d . . .
C7 C 0.24295(19) 0.91215(13) -0.01057(12) 0.0169(4) Uani 1 1 d . . .
H7A H 0.2576 0.8670 -0.0415 0.020 Uiso 1 1 calc R . .
C8 C 0.15788(19) 0.97188(14) -0.04821(12) 0.0205(4) Uani 1 1 d . . .
H8A H 0.1163 0.9666 -0.1044 0.025 Uiso 1 1 calc R . .
C9 C 0.13420(19) 1.03725(14) -0.00530(13) 0.0215(4) Uani 1 1 d . . .
H9A H 0.0802 1.0785 -0.0323 0.026 Uiso 1 1 calc R . .
C10 C 0.19007(19) 1.04355(12) 0.07941(13) 0.0179(4) Uani 1 1 d . . .
C11 C 0.1673(2) 1.10811(13) 0.12850(14) 0.0221(4) Uani 1 1 d . . .
H11A H 0.1123 1.1503 0.1047 0.026 Uiso 1 1 calc R . .
C12 C 0.2241(2) 1.10999(13) 0.20967(13) 0.0214(4) Uani 1 1 d . . .
H12A H 0.2126 1.1548 0.2421 0.026 Uiso 1 1 calc R . .
C13 C 0.30045(19) 1.04471(12) 0.24561(12) 0.0170(4) Uani 1 1 d . . .
C14 C 0.3577(2) 1.04624(13) 0.33606(13) 0.0258(5) Uani 1 1 d . . .
H14A H 0.4223 1.0042 0.3498 0.039 Uiso 1 1 calc R . .
H14B H 0.2911 1.0371 0.3661 0.039 Uiso 1 1 calc R . .
H14C H 0.3973 1.0984 0.3513 0.039 Uiso 1 1 calc R . .
C15 C 0.27216(17) 0.98221(12) 0.11843(12) 0.0141(4) Uani 1 1 d . . .
C16 C -0.0092(2) 0.80225(18) 0.21829(13) 0.0312(6) Uani 1 1 d . . .
C17 C 0.12876(19) 0.82404(13) 0.25954(12) 0.0173(4) Uani 1 1 d . . .
C18 C 0.15264(19) 0.84680(13) 0.34118(12) 0.0187(4) Uani 1 1 d . . .
H18A H 0.0821 0.8561 0.3650 0.022 Uiso 1 1 calc R . .
C19 C 0.27576(19) 0.85692(12) 0.39076(12) 0.0155(4) Uani 1 1 d . . .
C20 C 0.27662(19) 0.88375(14) 0.47917(13) 0.0210(4) Uani 1 1 d . . .
C21 C 0.50257(18) 0.83680(11) 0.41583(11) 0.0130(4) Uani 1 1 d . . .
C22 C 0.52898(19) 0.79138(12) 0.48665(12) 0.0157(4) Uani 1 1 d . . .
H22A H 0.4617 0.7648 0.5037 0.019 Uiso 1 1 calc R . .
C23 C 0.6544(2) 0.78393(12) 0.53396(12) 0.0182(4) Uani 1 1 d . . .
H23A H 0.6708 0.7522 0.5822 0.022 Uiso 1 1 calc R . .
C24 C 0.75248(19) 0.82217(12) 0.51068(12) 0.0175(4) Uani 1 1 d . . .
H24A H 0.8358 0.8197 0.5446 0.021 Uiso 1 1 calc R . .
C25 C 0.73018(19) 0.86531(11) 0.43638(12) 0.0150(4) Uani 1 1 d . . .
C26 C 0.82737(19) 0.90495(13) 0.40752(13) 0.0189(4) Uani 1 1 d . . .
H26A H 0.9121 0.9049 0.4395 0.023 Uiso 1 1 calc R . .
C27 C 0.79926(19) 0.94305(13) 0.33398(13) 0.0197(4) Uani 1 1 d . . .
H27A H 0.8638 0.9712 0.3154 0.024 Uiso 1 1 calc R . .
C28 C 0.67356(19) 0.94081(12) 0.28497(12) 0.0163(4) Uani 1 1 d . . .
C29 C 0.6458(2) 0.97878(14) 0.20167(13) 0.0226(4) Uani 1 1 d . . .
H29A H 0.5554 0.9725 0.1759 0.034 Uiso 1 1 calc R . .
H29B H 0.6971 0.9529 0.1677 0.034 Uiso 1 1 calc R . .
H29C H 0.6669 1.0358 0.2071 0.034 Uiso 1 1 calc R . .
C30 C 0.60573(18) 0.86995(11) 0.38687(11) 0.0128(4) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.0785(14) . ?
Zn1 O2 2.1150(14) . ?
Zn1 N3 2.1225(16) . ?
Zn1 N1 2.1419(16) . ?
Zn1 N2 2.1573(16) . ?
Zn1 N4 2.2087(16) . ?
F1 C1 1.338(2) . ?
F2 C1 1.343(3) . ?
F3 C1 1.336(3) . ?
F4 C5 1.342(2) . ?
F5 C5 1.342(2) . ?
F6 C5 1.329(2) . ?
F7 C16 1.310(3) . ?
F8 C16 1.329(4) . ?
F9 C16 1.299(3) . ?
F10 C20 1.330(2) . ?
F11 C20 1.336(3) . ?
F12 C20 1.345(3) . ?
O1 C2 1.261(2) . ?
O2 C17 1.259(2) . ?
N1 C4 1.309(2) . ?
N1 C6 1.410(2) . ?
N2 C13 1.326(3) . ?
N2 C15 1.377(2) . ?
N3 C19 1.310(3) . ?
N3 C21 1.410(2) . ?
N4 C28 1.325(3) . ?
N4 C30 1.375(2) . ?
C1 C2 1.526(3) . ?
C2 C3 1.382(3) . ?
C3 C4 1.417(3) . ?
C4 C5 1.543(3) . ?
C6 C7 1.381(3) . ?
C6 C15 1.428(3) . ?
C7 C8 1.407(3) . ?
C8 C9 1.365(3) . ?
C9 C10 1.414(3) . ?
C10 C11 1.413(3) . ?
C10 C15 1.416(3) . ?
C11 C12 1.359(3) . ?
C12 C13 1.418(3) . ?
C13 C14 1.501(3) . ?
C16 C17 1.537(3) . ?
C17 C18 1.386(3) . ?
C18 C19 1.409(3) . ?
C19 C20 1.545(3) . ?
C21 C22 1.383(3) . ?
C21 C30 1.425(3) . ?
C22 C23 1.411(3) . ?
C23 C24 1.368(3) . ?
C24 C25 1.412(3) . ?
C25 C30 1.412(3) . ?
C25 C26 1.416(3) . ?
C26 C27 1.359(3) . ?
C27 C28 1.419(3) . ?
C28 C29 1.500(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O2 90.83(5) . . ?
O1 Zn1 N3 87.61(6) . . ?
O2 Zn1 N3 84.57(6) . . ?
O1 Zn1 N1 84.98(5) . . ?
O2 Zn1 N1 89.97(6) . . ?
N3 Zn1 N1 170.73(6) . . ?
O1 Zn1 N2 162.62(6) . . ?
O2 Zn1 N2 91.03(6) . . ?
N3 Zn1 N2 109.77(6) . . ?
N1 Zn1 N2 77.75(6) . . ?
O1 Zn1 N4 87.96(6) . . ?
O2 Zn1 N4 161.88(6) . . ?
N3 Zn1 N4 77.31(6) . . ?
N1 Zn1 N4 107.92(6) . . ?
N2 Zn1 N4 95.50(6) . . ?
C2 O1 Zn1 120.90(12) . . ?
C17 O2 Zn1 123.81(12) . . ?
C4 N1 C6 126.14(16) . . ?
C4 N1 Zn1 122.83(13) . . ?
C6 N1 Zn1 109.79(12) . . ?
C13 N2 C15 119.08(17) . . ?
C13 N2 Zn1 129.62(13) . . ?
C15 N2 Zn1 109.68(12) . . ?
C19 N3 C21 125.05(16) . . ?
C19 N3 Zn1 123.33(13) . . ?
C21 N3 Zn1 110.74(12) . . ?
C28 N4 C30 119.19(17) . . ?
C28 N4 Zn1 130.13(13) . . ?
C30 N4 Zn1 108.90(12) . . ?
F3 C1 F1 106.57(17) . . ?
F3 C1 F2 106.56(17) . . ?
F1 C1 F2 106.91(18) . . ?
F3 C1 C2 111.19(17) . . ?
F1 C1 C2 114.54(16) . . ?
F2 C1 C2 110.65(17) . . ?
O1 C2 C3 129.79(18) . . ?
O1 C2 C1 112.65(16) . . ?
C3 C2 C1 117.55(17) . . ?
C2 C3 C4 123.77(18) . . ?
N1 C4 C3 123.43(17) . . ?
N1 C4 C5 124.04(17) . . ?
C3 C4 C5 112.52(16) . . ?
F6 C5 F4 106.19(16) . . ?
F6 C5 F5 107.87(16) . . ?
F4 C5 F5 106.16(16) . . ?
F6 C5 C4 113.72(16) . . ?
F4 C5 C4 110.91(16) . . ?
F5 C5 C4 111.57(16) . . ?
C7 C6 N1 125.58(18) . . ?
C7 C6 C15 118.59(18) . . ?
N1 C6 C15 115.65(16) . . ?
C6 C7 C8 120.85(19) . . ?
C9 C8 C7 121.00(19) . . ?
C8 C9 C10 120.00(19) . . ?
C11 C10 C9 123.38(19) . . ?
C11 C10 C15 117.34(19) . . ?
C9 C10 C15 119.28(19) . . ?
C12 C11 C10 120.11(19) . . ?
C11 C12 C13 119.58(19) . . ?
N2 C13 C12 121.93(18) . . ?
N2 C13 C14 119.24(18) . . ?
C12 C13 C14 118.83(18) . . ?
N2 C15 C10 121.77(18) . . ?
N2 C15 C6 118.52(17) . . ?
C10 C15 C6 119.71(18) . . ?
F9 C16 F7 107.1(2) . . ?
F9 C16 F8 108.3(3) . . ?
F7 C16 F8 104.5(2) . . ?
F9 C16 C17 111.6(2) . . ?
F7 C16 C17 115.18(17) . . ?
F8 C16 C17 109.8(2) . . ?
O2 C17 C18 129.22(18) . . ?
O2 C17 C16 113.84(17) . . ?
C18 C17 C16 116.94(18) . . ?
C17 C18 C19 123.64(18) . . ?
N3 C19 C18 123.98(18) . . ?
N3 C19 C20 122.45(17) . . ?
C18 C19 C20 113.54(17) . . ?
F10 C20 F11 108.05(17) . . ?
F10 C20 F12 106.10(18) . . ?
F11 C20 F12 106.32(17) . . ?
F10 C20 C19 112.82(17) . . ?
F11 C20 C19 112.76(18) . . ?
F12 C20 C19 110.37(17) . . ?
C22 C21 N3 124.57(18) . . ?
C22 C21 C30 118.75(17) . . ?
N3 C21 C30 116.39(16) . . ?
C21 C22 C23 121.01(18) . . ?
C24 C23 C22 120.35(18) . . ?
C23 C24 C25 120.16(18) . . ?
C24 C25 C30 119.67(18) . . ?
C24 C25 C26 123.31(18) . . ?
C30 C25 C26 117.02(18) . . ?
C27 C26 C25 119.91(18) . . ?
C26 C27 C28 119.98(19) . . ?
N4 C28 C27 121.51(18) . . ?
N4 C28 C29 119.16(17) . . ?
C27 C28 C29 119.32(18) . . ?
N4 C30 C25 122.14(18) . . ?
N4 C30 C21 118.37(17) . . ?
C25 C30 C21 119.50(17) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.964
_refine_diff_density_min         -0.850
_refine_diff_density_rms         0.071
_database_code_depnum_ccdc_archive 'CCDC 1005752'
