# 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_DPNDI

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H12 N4 O4, 2(C5 H9 N O)'
_chemical_formula_sum            'C34 H30 N6 O6'
_chemical_formula_weight         618.64

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'

_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                   21.341(5)
_cell_length_b                   6.9041(14)
_cell_length_c                   21.272(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.30(3)
_cell_angle_gamma                90.00
_cell_volume                     3050.2(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       monoclinic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9215
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'RAPID-AUTO; Rigaku, 1998'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14511
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         27.44
_reflns_number_total             3468
_reflns_number_gt                2189
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Inc., 1998)'
_computing_cell_refinement       'RAPID-AUTO (Rigaku Inc., 1998)'
_computing_data_reduction        'RAPID-AUTO (Rigaku Inc., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2004)'
_computing_publication_material  'SHELXL97 and publCIF (Westrip, 2010)'

_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)+(0.0905P)²+1.2626P] 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     SHELXL
_refine_ls_extinction_coef       0.0031(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3468
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1797
_refine_ls_wR_factor_gt          0.1600
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.22867(9) 0.2861(2) 0.11992(8) 0.0718(6) Uani 1 1 d . . .
O2 O 0.36779(7) 0.7805(2) 0.18707(6) 0.0563(4) Uani 1 1 d . . .
N1 N 0.29818(8) 0.5333(2) 0.15350(7) 0.0424(4) Uani 1 1 d . . .
N2 N 0.35098(11) 0.2435(3) 0.33280(9) 0.0657(6) Uani 1 1 d . . .
C1 C 0.33316(10) 0.9709(3) 0.06593(9) 0.0455(5) Uani 1 1 d . . .
H1 H 0.3644 1.0304 0.0978 0.055 Uiso 1 1 calc R . .
C2 C 0.30666(9) 0.7992(3) 0.07906(8) 0.0379(4) Uani 1 1 d . . .
C3 C 0.25956(9) 0.7067(2) 0.03086(8) 0.0362(4) Uani 1 1 d . . .
C4 C 0.23158(9) 0.5292(3) 0.04264(9) 0.0397(4) Uani 1 1 d . . .
C5 C 0.18613(10) 0.4419(3) -0.00496(9) 0.0469(5) Uani 1 1 d . . .
H5 H 0.1680 0.3246 0.0031 0.056 Uiso 1 1 calc R . .
C6 C 0.32737(10) 0.7089(3) 0.14394(9) 0.0411(5) Uani 1 1 d . . .
C7 C 0.25115(10) 0.4369(3) 0.10687(9) 0.0462(5) Uani 1 1 d . . .
C8 C 0.31820(10) 0.4385(3) 0.21566(9) 0.0432(5) Uani 1 1 d . . .
C9 C 0.30093(11) 0.5119(3) 0.26929(9) 0.0490(5) Uani 1 1 d . . .
H9 H 0.2779 0.6270 0.2673 0.059 Uiso 1 1 calc R . .
C10 C 0.31891(12) 0.4092(3) 0.32635(10) 0.0566(6) Uani 1 1 d . . .
H10 H 0.3077 0.4599 0.3627 0.068 Uiso 1 1 calc R . .
C11 C 0.36738(15) 0.1782(4) 0.28025(12) 0.0736(8) Uani 1 1 d . . .
H11 H 0.3901 0.0623 0.2834 0.088 Uiso 1 1 calc R . .
C12 C 0.35291(12) 0.2710(3) 0.22101(11) 0.0612(6) Uani 1 1 d . . .
H12 H 0.3665 0.2206 0.1858 0.073 Uiso 1 1 calc R . .
O3 O 0.09054(11) -0.1097(4) 0.42524(11) 0.1056(8) Uani 1 1 d . . .
N3 N 0.03954(12) 0.1624(4) 0.44351(13) 0.0887(8) Uani 1 1 d . . .
C13 C -0.0116(2) 0.2928(6) 0.4096(3) 0.1248(16) Uani 1 1 d . . .
H13A H 0.0023 0.4269 0.4134 0.150 Uiso 1 1 calc R . .
H13B H -0.0503 0.2796 0.4259 0.150 Uiso 1 1 calc R . .
C14 C -0.0224(2) 0.2216(8) 0.3402(3) 0.1403(17) Uani 1 1 d . . .
H14A H -0.0681 0.2131 0.3206 0.168 Uiso 1 1 calc R . .
H14B H -0.0028 0.3098 0.3149 0.168 Uiso 1 1 calc R . .
C15 C 0.00662(16) 0.0357(5) 0.34262(15) 0.0933(10) Uani 1 1 d . . .
H15A H 0.0309 0.0239 0.3094 0.112 Uiso 1 1 calc R . .
H15B H -0.0259 -0.0650 0.3361 0.112 Uiso 1 1 calc R . .
C16 C 0.05103(13) 0.0188(4) 0.40933(14) 0.0715(7) Uani 1 1 d . . .
C17 C 0.0706(2) 0.1792(8) 0.51101(16) 0.152(2) Uani 1 1 d . . .
H17A H 0.0557 0.2941 0.5284 0.228 Uiso 1 1 calc R . .
H17B H 0.1164 0.1869 0.5158 0.228 Uiso 1 1 calc R . .
H17C H 0.0605 0.0679 0.5338 0.228 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
O1 C7 1.205(2) . ?
O2 C6 1.211(2) . ?
N1 C6 1.399(2) . ?
N1 C7 1.406(3) . ?
N1 C8 1.449(2) . ?
N2 C10 1.324(3) . ?
N2 C11 1.325(3) . ?
C1 C2 1.369(3) . ?
C1 C5 1.403(3) 7_565 ?
C1 H1 0.9300 . ?
C2 C3 1.413(2) . ?
C2 C6 1.486(3) . ?
C3 C4 1.411(2) . ?
C3 C3 1.414(3) 7_565 ?
C4 C5 1.370(3) . ?
C4 C7 1.478(3) . ?
C5 C1 1.403(3) 7_565 ?
C5 H5 0.9300 . ?
C8 C12 1.364(3) . ?
C8 C9 1.374(3) . ?
C9 C10 1.382(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.384(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
O3 C16 1.217(3) . ?
N3 C16 1.286(4) . ?
N3 C17 1.441(4) . ?
N3 C13 1.470(5) . ?
C13 C14 1.522(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.420(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.519(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C6 N1 C7 125.26(15) . . ?
C6 N1 C8 118.47(15) . . ?
C7 N1 C8 116.26(15) . . ?
C10 N2 C11 115.92(19) . . ?
C2 C1 C5 120.87(18) . 7_565 ?
C2 C1 H1 119.6 . . ?
C5 C1 H1 119.6 7_565 . ?
C1 C2 C3 120.10(17) . . ?
C1 C2 C6 120.26(16) . . ?
C3 C2 C6 119.63(16) . . ?
C4 C3 C2 121.56(16) . . ?
C4 C3 C3 119.2(2) . 7_565 ?
C2 C3 C3 119.2(2) . 7_565 ?
C5 C4 C3 120.50(17) . . ?
C5 C4 C7 119.68(17) . . ?
C3 C4 C7 119.83(16) . . ?
C4 C5 C1 120.09(18) . 7_565 ?
C4 C5 H5 120.0 . . ?
C1 C5 H5 120.0 7_565 . ?
O2 C6 N1 120.47(17) . . ?
O2 C6 C2 122.69(18) . . ?
N1 C6 C2 116.83(16) . . ?
O1 C7 N1 120.27(18) . . ?
O1 C7 C4 122.84(18) . . ?
N1 C7 C4 116.89(16) . . ?
C12 C8 C9 119.21(18) . . ?
C12 C8 N1 119.99(17) . . ?
C9 C8 N1 120.77(17) . . ?
C8 C9 C10 117.80(19) . . ?
C8 C9 H9 121.1 . . ?
C10 C9 H9 121.1 . . ?
N2 C10 C9 124.56(19) . . ?
N2 C10 H10 117.7 . . ?
C9 C10 H10 117.7 . . ?
N2 C11 C12 124.3(2) . . ?
N2 C11 H11 117.8 . . ?
C12 C11 H11 117.8 . . ?
C8 C12 C11 118.1(2) . . ?
C8 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
C16 N3 C17 121.4(4) . . ?
C16 N3 C13 114.3(3) . . ?
C17 N3 C13 124.0(4) . . ?
N3 C13 C14 102.0(3) . . ?
N3 C13 H13A 111.4 . . ?
C14 C13 H13A 111.4 . . ?
N3 C13 H13B 111.4 . . ?
C14 C13 H13B 111.4 . . ?
H13A C13 H13B 109.2 . . ?
C15 C14 C13 106.8(3) . . ?
C15 C14 H14A 110.4 . . ?
C13 C14 H14A 110.4 . . ?
C15 C14 H14B 110.4 . . ?
C13 C14 H14B 110.4 . . ?
H14A C14 H14B 108.6 . . ?
C14 C15 C16 106.0(3) . . ?
C14 C15 H15A 110.5 . . ?
C16 C15 H15A 110.5 . . ?
C14 C15 H15B 110.5 . . ?
C16 C15 H15B 110.5 . . ?
H15A C15 H15B 108.7 . . ?
O3 C16 N3 127.9(3) . . ?
O3 C16 C15 124.0(3) . . ?
N3 C16 C15 108.0(3) . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 C3 0.4(3) 7_565 . . . ?
C5 C1 C2 C6 -179.75(18) 7_565 . . . ?
C1 C2 C3 C4 179.59(17) . . . . ?
C6 C2 C3 C4 -0.2(3) . . . . ?
C1 C2 C3 C3 0.2(3) . . . 7_565 ?
C6 C2 C3 C3 -179.6(2) . . . 7_565 ?
C2 C3 C4 C5 -179.78(18) . . . . ?
C3 C3 C4 C5 -0.4(3) 7_565 . . . ?
C2 C3 C4 C7 0.5(3) . . . . ?
C3 C3 C4 C7 179.9(2) 7_565 . . . ?
C3 C4 C5 C1 -0.2(3) . . . 7_565 ?
C7 C4 C5 C1 179.45(18) . . . 7_565 ?
C7 N1 C6 O2 -179.62(19) . . . . ?
C8 N1 C6 O2 -1.0(3) . . . . ?
C7 N1 C6 C2 -0.1(3) . . . . ?
C8 N1 C6 C2 178.57(16) . . . . ?
C1 C2 C6 O2 -0.3(3) . . . . ?
C3 C2 C6 O2 179.53(18) . . . . ?
C1 C2 C6 N1 -179.82(17) . . . . ?
C3 C2 C6 N1 0.0(3) . . . . ?
C6 N1 C7 O1 -179.7(2) . . . . ?
C8 N1 C7 O1 1.6(3) . . . . ?
C6 N1 C7 C4 0.4(3) . . . . ?
C8 N1 C7 C4 -178.31(16) . . . . ?
C5 C4 C7 O1 -0.2(3) . . . . ?
C3 C4 C7 O1 179.5(2) . . . . ?
C5 C4 C7 N1 179.73(18) . . . . ?
C3 C4 C7 N1 -0.6(3) . . . . ?
C6 N1 C8 C12 -109.7(2) . . . . ?
C7 N1 C8 C12 69.1(3) . . . . ?
C6 N1 C8 C9 72.3(3) . . . . ?
C7 N1 C8 C9 -108.9(2) . . . . ?
C12 C8 C9 C10 -1.1(3) . . . . ?
N1 C8 C9 C10 176.87(19) . . . . ?
C11 N2 C10 C9 1.5(4) . . . . ?
C8 C9 C10 N2 -0.8(4) . . . . ?
C10 N2 C11 C12 -0.3(4) . . . . ?
C9 C8 C12 C11 2.2(4) . . . . ?
N1 C8 C12 C11 -175.8(2) . . . . ?
N2 C11 C12 C8 -1.6(4) . . . . ?
C16 N3 C13 C14 -10.5(4) . . . . ?
C17 N3 C13 C14 175.4(3) . . . . ?
N3 C13 C14 C15 16.2(5) . . . . ?
C13 C14 C15 C16 -16.2(5) . . . . ?
C17 N3 C16 O3 -5.8(5) . . . . ?
C13 N3 C16 O3 179.9(3) . . . . ?
C17 N3 C16 C15 175.2(3) . . . . ?
C13 N3 C16 C15 0.9(3) . . . . ?
C14 C15 C16 O3 -169.1(3) . . . . ?
C14 C15 C16 N3 10.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.062
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_database_code_depnum_ccdc_archive 'CCDC 1028277'
#######################################################################
#
#                 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_p4mmm

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H1.45 F0.75 N O Si0.13 Zn0.13'
_chemical_formula_sum            'C6 H1.45 F0.75 N O Si0.13 Zn0.13'
_chemical_formula_weight         129.47

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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'
O O 0.0106 0.0060 '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           tetragonal
_symmetry_space_group_name_H-M   P4/mmm
_symmetry_space_group_name_Hall  '-P 4 2'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x, z'
'-x, -y, z'
'y, -x, z'
'x, -y, -z'
'-x, y, -z'
'y, x, -z'
'-y, -x, -z'
'-x, -y, -z'
'y, -x, -z'
'x, y, -z'
'-y, x, -z'
'-x, y, z'
'x, -y, z'
'-y, -x, z'
'y, x, z'

_cell_length_a                   19.702(4)
_cell_length_b                   19.702(4)
_cell_length_c                   7.4311(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2884.6(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             518
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8125
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24189
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0183
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.59
_diffrn_reflns_theta_max         27.56
_reflns_number_total             1968
_reflns_number_gt                1960
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2004)'
_computing_publication_material  'SHELXL97 and publCIF (Westrip, 2010)'

_refine_special_details          SQUEEZE
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 -0.002 -0.002 -0.027 1978 221 ' '
_platon_squeeze_details          
;
;

_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)+(0.1393P)²+1.4985P] 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         1968
_refine_ls_number_parameters     83
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0641
_refine_ls_wR_factor_ref         0.2038
_refine_ls_wR_factor_gt          0.2035
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.010
_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 0.5000 0.5000 0.5000 0.0213(3) Uani 1 16 d S . .
Si1 Si 0.5000 0.5000 0.0000 0.0266(4) Uani 1 16 d S . .
F1 F 0.44041(8) 0.44041(8) 0.0000 0.0438(6) Uani 1 4 d S . .
F2 F 0.5000 0.5000 0.2296(4) 0.0311(7) Uani 1 8 d S . .
O1 O 0.38566(18) 0.17849(13) 0.5000 0.0919(12) Uani 1 2 d S A .
N1 N 0.5000 0.39066(15) 0.5000 0.0334(7) Uani 1 4 d S . .
N2 N 0.5000 0.17776(15) 0.5000 0.0476(9) Uani 1 4 d S . .
C1A C 0.5000 0.288(3) 0.352(9) 0.050(17) Uani 0.23(6) 2 d SP A 1
H1A H 0.5000 0.2653 0.2387 0.060 Uiso 0.23(6) 2 calc SPR A 1
C2A C 0.5000 0.361(5) 0.355(11) 0.048(16) Uani 0.23(6) 2 d SP A 1
H2A H 0.5000 0.3858 0.2452 0.058 Uiso 0.23(6) 2 calc SPR A 1
C1B C 0.5226(14) 0.2854(7) 0.347(2) 0.047(5) Uani 0.39(3) 1 d P . 2
C2B C 0.5182(19) 0.3529(15) 0.352(3) 0.047(5) Uani 0.39(3) 1 d P . 2
C3 C 0.5000 0.2511(2) 0.5000 0.0532(12) Uani 1 4 d S . .
C4 C 0.4373(2) 0.14602(18) 0.5000 0.0675(12) Uani 1 2 d S . .
C5 C 0.4387(2) 0.07031(17) 0.5000 0.0654(11) Uani 1 2 d S A .
C6 C 0.5000 0.0357(2) 0.5000 0.0529(12) Uani 1 4 d S . .
C7 C 0.3777(3) 0.03536(18) 0.5000 0.0883(18) Uani 1 2 d S . .
H7 H 0.3360 0.0595 0.5000 0.106 Uiso 1 2 calc SR A .


_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 F2 2.009(3) . ?
Zn1 F2 2.009(3) 9_666 ?
Zn1 N1 2.154(3) 10_566 ?
Zn1 N1 2.154(3) 9_666 ?
Zn1 N1 2.154(3) . ?
Zn1 N1 2.154(3) 2_655 ?
Si1 F1 1.660(2) 9_665 ?
Si1 F1 1.660(2) 10_565 ?
Si1 F1 1.660(2) . ?
Si1 F1 1.660(2) 2_655 ?
Si1 F2 1.706(3) 9_665 ?
Si1 F2 1.706(3) . ?
O1 C4 1.202(5) . ?
N1 C2A 1.23(9) . ?
N1 C2A 1.23(9) 11_556 ?
N1 C2B 1.37(2) 13_655 ?
N1 C2B 1.37(2) . ?
N1 C2B 1.37(2) 6_656 ?
N1 C2B 1.37(2) 11_556 ?
N2 C4 1.384(5) . ?
N2 C4 1.384(5) 13_655 ?
N2 C3 1.445(5) . ?
C1A C3 1.32(6) . ?
C1A C2A 1.44(12) . ?
C1A H1A 0.9500 . ?
C2A H2A 0.9500 . ?
C1B C1B 0.89(6) 13_655 ?
C1B C2B 1.33(3) . ?
C1B C3 1.396(15) . ?
C1B C2B 1.55(4) 13_655 ?
C2B C2B 0.72(8) 13_655 ?
C2B C1B 1.55(4) 13_655 ?
C3 C1A 1.32(6) 11_556 ?
C3 C1B 1.396(15) 6_656 ?
C3 C1B 1.396(15) 11_556 ?
C3 C1B 1.396(15) 13_655 ?
C4 C5 1.492(5) . ?
C5 C7 1.386(6) . ?
C5 C6 1.386(5) . ?
C6 C5 1.386(5) 13_655 ?
C6 C6 1.407(8) 9_656 ?
C7 C7 1.393(7) 5_556 ?
C7 H7 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
F2 Zn1 F2 180.000(1) . 9_666 ?
F2 Zn1 N1 90.000(1) . 10_566 ?
F2 Zn1 N1 90.000(1) 9_666 10_566 ?
F2 Zn1 N1 90.0 . 9_666 ?
F2 Zn1 N1 90.0 9_666 9_666 ?
N1 Zn1 N1 90.0 10_566 9_666 ?
F2 Zn1 N1 90.0 . . ?
F2 Zn1 N1 90.0 9_666 . ?
N1 Zn1 N1 90.0 10_566 . ?
N1 Zn1 N1 180.000(1) 9_666 . ?
F2 Zn1 N1 90.000(1) . 2_655 ?
F2 Zn1 N1 90.000(1) 9_666 2_655 ?
N1 Zn1 N1 180.0 10_566 2_655 ?
N1 Zn1 N1 90.0 9_666 2_655 ?
N1 Zn1 N1 90.0 . 2_655 ?
F1 Si1 F1 90.0 9_665 10_565 ?
F1 Si1 F1 180.0 9_665 . ?
F1 Si1 F1 90.0 10_565 . ?
F1 Si1 F1 90.0 9_665 2_655 ?
F1 Si1 F1 180.00(8) 10_565 2_655 ?
F1 Si1 F1 90.0 . 2_655 ?
F1 Si1 F2 90.0 9_665 9_665 ?
F1 Si1 F2 90.0 10_565 9_665 ?
F1 Si1 F2 90.0 . 9_665 ?
F1 Si1 F2 90.0 2_655 9_665 ?
F1 Si1 F2 90.0 9_665 . ?
F1 Si1 F2 90.0 10_565 . ?
F1 Si1 F2 90.0 . . ?
F1 Si1 F2 90.0 2_655 . ?
F2 Si1 F2 180.0 9_665 . ?
Si1 F2 Zn1 180.0 . . ?
C2A N1 C2A 123(9) . 11_556 ?
C2A N1 C2B 16.1(15) . 13_655 ?
C2A N1 C2B 116(3) 11_556 13_655 ?
C2A N1 C2B 16.1(15) . . ?
C2A N1 C2B 116(3) 11_556 . ?
C2B N1 C2B 30(3) 13_655 . ?
C2A N1 C2B 116(3) . 6_656 ?
C2A N1 C2B 16.1(16) 11_556 6_656 ?
C2B N1 C2B 106.1(18) 13_655 6_656 ?
C2B N1 C2B 114(3) . 6_656 ?
C2A N1 C2B 116(3) . 11_556 ?
C2A N1 C2B 16.1(15) 11_556 11_556 ?
C2B N1 C2B 114(3) 13_655 11_556 ?
C2B N1 C2B 106.1(18) . 11_556 ?
C2B N1 C2B 30(3) 6_656 11_556 ?
C2A N1 Zn1 119(4) . . ?
C2A N1 Zn1 119(4) 11_556 . ?
C2B N1 Zn1 122.8(13) 13_655 . ?
C2B N1 Zn1 122.8(13) . . ?
C2B N1 Zn1 122.8(13) 6_656 . ?
C2B N1 Zn1 122.8(13) 11_556 . ?
C4 N2 C4 126.3(4) . 13_655 ?
C4 N2 C3 116.87(19) . . ?
C4 N2 C3 116.86(19) 13_655 . ?
C3 C1A C2A 122(6) . . ?
C3 C1A H1A 118.8 . . ?
C2A C1A H1A 118.8 . . ?
N1 C2A C1A 119(7) . . ?
N1 C2A H2A 120.3 . . ?
C1A C2A H2A 120.3 . . ?
C1B C1B C2B 86(2) 13_655 . ?
C1B C1B C3 71.4(12) 13_655 . ?
C2B C1B C3 115.9(14) . . ?
C1B C1B C2B 58.9(15) 13_655 13_655 ?
C2B C1B C2B 27(3) . 13_655 ?
C3 C1B C2B 103.2(15) . 13_655 ?
C2B C2B C1B 94(2) 13_655 . ?
C2B C2B N1 74.9(17) 13_655 . ?
C1B C2B N1 126(2) . . ?
C2B C2B C1B 58.9(15) 13_655 13_655 ?
C1B C2B C1B 35(2) . 13_655 ?
N1 C2B C1B 110(2) . 13_655 ?
C1A C3 C1A 113(6) 11_556 . ?
C1A C3 C1B 18.7(10) 11_556 6_656 ?
C1A C3 C1B 115(2) . 6_656 ?
C1A C3 C1B 18.7(10) 11_556 11_556 ?
C1A C3 C1B 115(2) . 11_556 ?
C1B C3 C1B 37(2) 6_656 11_556 ?
C1A C3 C1B 115(2) 11_556 13_655 ?
C1A C3 C1B 18.7(10) . 13_655 ?
C1B C3 C1B 109.2(18) 6_656 13_655 ?
C1B C3 C1B 122.1(12) 11_556 13_655 ?
C1A C3 C1B 115(2) 11_556 . ?
C1A C3 C1B 18.7(10) . . ?
C1B C3 C1B 122.1(12) 6_656 . ?
C1B C3 C1B 109.2(18) 11_556 . ?
C1B C3 C1B 37(2) 13_655 . ?
C1A C3 N2 123(3) 11_556 . ?
C1A C3 N2 123(3) . . ?
C1B C3 N2 118.9(6) 6_656 . ?
C1B C3 N2 118.9(6) 11_556 . ?
C1B C3 N2 118.9(6) 13_655 . ?
C1B C3 N2 118.9(6) . . ?
O1 C4 N2 121.0(3) . . ?
O1 C4 C5 123.2(4) . . ?
N2 C4 C5 115.8(4) . . ?
C7 C5 C6 120.7(3) . . ?
C7 C5 C4 118.7(4) . . ?
C6 C5 C4 120.5(4) . . ?
C5 C6 C5 121.1(4) 13_655 . ?
C5 C6 C6 119.5(2) 13_655 9_656 ?
C5 C6 C6 119.5(2) . 9_656 ?
C5 C7 C7 119.8(2) . 5_556 ?
C5 C7 H7 120.1 . . ?
C7 C7 H7 120.1 5_556 . ?

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
F1 Si1 F2 Zn1 0(100) 9_665 . . . ?
F1 Si1 F2 Zn1 -90(100) 10_565 . . . ?
F1 Si1 F2 Zn1 180(100) . . . . ?
F1 Si1 F2 Zn1 90(100) 2_655 . . . ?
F2 Si1 F2 Zn1 0(100) 9_665 . . . ?
F2 Zn1 F2 Si1 0(100) 9_666 . . . ?
N1 Zn1 F2 Si1 135(100) 10_566 . . . ?
N1 Zn1 F2 Si1 45(100) 9_666 . . . ?
N1 Zn1 F2 Si1 -135(100) . . . . ?
N1 Zn1 F2 Si1 -45(100) 2_655 . . . ?
F2 Zn1 N1 C2A 0.00(2) . . . . ?
F2 Zn1 N1 C2A 180.00(2) 9_666 . . . ?
N1 Zn1 N1 C2A 90.00(2) 10_566 . . . ?
N1 Zn1 N1 C2A 90(100) 9_666 . . . ?
N1 Zn1 N1 C2A -90.00(2) 2_655 . . . ?
F2 Zn1 N1 C2A 180.00(3) . . . 11_556 ?
F2 Zn1 N1 C2A 0.00(3) 9_666 . . 11_556 ?
N1 Zn1 N1 C2A -90.00(2) 10_566 . . 11_556 ?
N1 Zn1 N1 C2A -90(100) 9_666 . . 11_556 ?
N1 Zn1 N1 C2A 90.00(2) 2_655 . . 11_556 ?
F2 Zn1 N1 C2B -18.1(19) . . . 13_655 ?
F2 Zn1 N1 C2B 161.9(19) 9_666 . . 13_655 ?
N1 Zn1 N1 C2B 71.9(19) 10_566 . . 13_655 ?
N1 Zn1 N1 C2B 72(100) 9_666 . . 13_655 ?
N1 Zn1 N1 C2B -108.1(19) 2_655 . . 13_655 ?
F2 Zn1 N1 C2B 18.1(19) . . . . ?
F2 Zn1 N1 C2B -161.9(19) 9_666 . . . ?
N1 Zn1 N1 C2B 108.1(19) 10_566 . . . ?
N1 Zn1 N1 C2B 108(100) 9_666 . . . ?
N1 Zn1 N1 C2B -71.9(19) 2_655 . . . ?
F2 Zn1 N1 C2B -161.9(19) . . . 6_656 ?
F2 Zn1 N1 C2B 18.1(19) 9_666 . . 6_656 ?
N1 Zn1 N1 C2B -71.9(19) 10_566 . . 6_656 ?
N1 Zn1 N1 C2B -72(100) 9_666 . . 6_656 ?
N1 Zn1 N1 C2B 108.1(19) 2_655 . . 6_656 ?
F2 Zn1 N1 C2B 161.9(19) . . . 11_556 ?
F2 Zn1 N1 C2B -18.1(19) 9_666 . . 11_556 ?
N1 Zn1 N1 C2B -108.1(19) 10_566 . . 11_556 ?
N1 Zn1 N1 C2B -108(100) 9_666 . . 11_556 ?
N1 Zn1 N1 C2B 71.9(19) 2_655 . . 11_556 ?
C2A N1 C2A C1A 0.00(3) 11_556 . . . ?
C2B N1 C2A C1A -70(19) 13_655 . . . ?
C2B N1 C2A C1A 70(19) . . . . ?
C2B N1 C2A C1A -16.9(16) 6_656 . . . ?
C2B N1 C2A C1A 16.9(16) 11_556 . . . ?
Zn1 N1 C2A C1A 180.000(14) . . . . ?
C3 C1A C2A N1 0.00(2) . . . . ?
C1B C1B C2B C2B 0.0 13_655 . . 13_655 ?
C3 C1B C2B C2B -67(2) . . . 13_655 ?
C1B C1B C2B N1 74(3) 13_655 . . . ?
C3 C1B C2B N1 7(5) . . . . ?
C2B C1B C2B N1 74(3) 13_655 . . . ?
C3 C1B C2B C1B -67(2) . . . 13_655 ?
C2B C1B C2B C1B 0.0 13_655 . . 13_655 ?
C2A N1 C2B C2B -21(20) . . . 13_655 ?
C2A N1 C2B C2B 97.7(9) 11_556 . . 13_655 ?
C2B N1 C2B C2B 80.0(9) 6_656 . . 13_655 ?
C2B N1 C2B C2B 111(3) 11_556 . . 13_655 ?
Zn1 N1 C2B C2B -100.0(9) . . . 13_655 ?
C2A N1 C2B C1B -104(22) . . . . ?
C2A N1 C2B C1B 14(4) 11_556 . . . ?
C2B N1 C2B C1B -84(3) 13_655 . . . ?
C2B N1 C2B C1B -4(3) 6_656 . . . ?
C2B N1 C2B C1B 27(6) 11_556 . . . ?
Zn1 N1 C2B C1B 176(3) . . . . ?
C2A N1 C2B C1B -68(20) . . . 13_655 ?
C2A N1 C2B C1B 50(2) 11_556 . . 13_655 ?
C2B N1 C2B C1B -47.8(19) 13_655 . . 13_655 ?
C2B N1 C2B C1B 32.2(12) 6_656 . . 13_655 ?
C2B N1 C2B C1B 63(4) 11_556 . . 13_655 ?
Zn1 N1 C2B C1B -147.8(12) . . . 13_655 ?
C2A C1A C3 C1A 0.00(3) . . . 11_556 ?
C2A C1A C3 C1B 20.5(15) . . . 6_656 ?
C2A C1A C3 C1B -20.5(15) . . . 11_556 ?
C2A C1A C3 C1B 98(10) . . . 13_655 ?
C2A C1A C3 C1B -98(10) . . . . ?
C2A C1A C3 N2 180.000(16) . . . . ?
C1B C1B C3 C1A -98.8(13) 13_655 . . 11_556 ?
C2B C1B C3 C1A -23(4) . . . 11_556 ?
C2B C1B C3 C1A -48(3) 13_655 . . 11_556 ?
C1B C1B C3 C1A -8(11) 13_655 . . . ?
C2B C1B C3 C1A 68(10) . . . . ?
C2B C1B C3 C1A 42(10) 13_655 . . . ?
C1B C1B C3 C1B -79.3(8) 13_655 . . 6_656 ?
C2B C1B C3 C1B -3(2) . . . 6_656 ?
C2B C1B C3 C1B -28.9(12) 13_655 . . 6_656 ?
C1B C1B C3 C1B -118.2(14) 13_655 . . 11_556 ?
C2B C1B C3 C1B -42(4) . . . 11_556 ?
C2B C1B C3 C1B -68(3) 13_655 . . 11_556 ?
C2B C1B C3 C1B 76(3) . . . 13_655 ?
C2B C1B C3 C1B 50.4(18) 13_655 . . 13_655 ?
C1B C1B C3 N2 100.7(8) 13_655 . . . ?
C2B C1B C3 N2 177(2) . . . . ?
C2B C1B C3 N2 151.1(12) 13_655 . . . ?
C4 N2 C3 C1A 90.000(17) . . . 11_556 ?
C4 N2 C3 C1A -90.000(17) 13_655 . . 11_556 ?
C4 N2 C3 C1A -90.000(18) . . . . ?
C4 N2 C3 C1A 90.000(18) 13_655 . . . ?
C4 N2 C3 C1B 68.7(14) . . . 6_656 ?
C4 N2 C3 C1B -111.3(14) 13_655 . . 6_656 ?
C4 N2 C3 C1B 111.3(14) . . . 11_556 ?
C4 N2 C3 C1B -68.7(14) 13_655 . . 11_556 ?
C4 N2 C3 C1B -68.7(14) . . . 13_655 ?
C4 N2 C3 C1B 111.3(14) 13_655 . . 13_655 ?
C4 N2 C3 C1B -111.3(14) . . . . ?
C4 N2 C3 C1B 68.7(14) 13_655 . . . ?
C4 N2 C4 O1 180.0 13_655 . . . ?
C3 N2 C4 O1 0.0 . . . . ?
C4 N2 C4 C5 0.0 13_655 . . . ?
C3 N2 C4 C5 180.0 . . . . ?
O1 C4 C5 C7 0.0 . . . . ?
N2 C4 C5 C7 180.0 . . . . ?
O1 C4 C5 C6 180.0 . . . . ?
N2 C4 C5 C6 0.0 . . . . ?
C7 C5 C6 C5 180.0 . . . 13_655 ?
C4 C5 C6 C5 0.0 . . . 13_655 ?
C7 C5 C6 C6 0.0 . . . 9_656 ?
C4 C5 C6 C6 180.0 . . . 9_656 ?
C6 C5 C7 C7 0.0 . . . 5_556 ?
C4 C5 C7 C7 180.0 . . . 5_556 ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.498
_refine_diff_density_min         -1.114
_refine_diff_density_rms         0.081
_chemical_properties_physical    Light-sensitive
_database_code_depnum_ccdc_archive 'CCDC 1025385'
#######################################################################
#
#                 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_p4mmm

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H3 F0.75 N O Si0.13 Zn0.13, 0.205(I)'
_chemical_formula_sum            'C6 H3 F0.75 I0.20 N O Si0.13 Zn0.13'
_chemical_formula_weight         157.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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'
I I -0.4742 1.8119 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   P4/mmm
_symmetry_space_group_name_Hall  '-P 4 2'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x, z'
'-x, -y, z'
'y, -x, z'
'x, -y, -z'
'-x, y, -z'
'y, x, -z'
'-y, -x, -z'
'-x, -y, -z'
'y, -x, -z'
'x, y, -z'
'-y, x, -z'
'-x, y, z'
'x, -y, z'
'-y, -x, z'
'y, x, z'

_cell_length_a                   19.739(3)
_cell_length_b                   19.739(3)
_cell_length_c                   7.4768(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2913.2(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.716
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             617
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8348
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24611
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         27.52
_reflns_number_total             1984
_reflns_number_gt                1961
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2004)'
_computing_publication_material  'SHELXL97 and publCIF (Westrip, 2010)'

_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. 
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.500 -0.139 1797 195 ' '
_platon_squeeze_details          
;
;

_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)+(0.2477P)²+2.3190P] 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         1984
_refine_ls_number_parameters     72
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.1088
_refine_ls_wR_factor_ref         0.3465
_refine_ls_wR_factor_gt          0.3423
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_restrained_S_all      1.186
_refine_ls_shift/su_max          0.010
_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 0.0000 0.0000 0.0000 0.0193(5) Uani 1 16 d S . .
I1 I 0.3577(2) 0.0000 -0.5000 0.297(9) Uani 0.205(3) 4 d SP . .
I2 I 0.5000 0.0000 -0.5000 0.205(5) Uani 0.410(6) 8 d SP . .
Si1 Si 0.0000 0.0000 0.5000 0.0279(8) Uani 1 16 d S . .
F1 F 0.0000 0.0000 0.2715(6) 0.0313(12) Uani 1 8 d S . .
F2 F 0.05982(15) 0.05982(15) 0.5000 0.0408(11) Uani 1 4 d S . .
O1 O 0.3217(2) 0.1149(3) 0.0000 0.0864(19) Uani 1 2 d S . .
N1 N 0.1096(3) 0.0000 0.0000 0.0333(12) Uani 1 4 d S . .
N2 N 0.3226(3) 0.0000 0.0000 0.0530(18) Uani 1 4 d S . .
C1 C 0.1445(3) 0.0000 -0.1462(7) 0.102(4) Uani 1 2 d S . .
H1 H 0.1205 0.0000 -0.2563 0.122 Uiso 1 2 calc SR . .
C2 C 0.2141(3) 0.0000 -0.1528(8) 0.110(5) Uani 1 2 d S . .
H2 H 0.2369 0.0000 -0.2646 0.132 Uiso 1 2 calc SR . .
C3 C 0.2491(3) 0.0000 0.0000 0.050(2) Uani 1 4 d S . .
C4 C 0.3546(3) 0.0625(4) 0.0000 0.0616(18) Uani 1 2 d S . .
C5 C 0.4297(3) 0.0628(4) 0.0000 0.0557(16) Uani 1 2 d S . .
C6 C 0.4643(3) 0.0000 0.0000 0.0467(18) Uani 1 4 d S . .
C7 C 0.4642(3) 0.1211(4) 0.0000 0.073(2) Uani 1 2 d S . .
H7 H 0.4404 0.1629 0.0000 0.088 Uiso 1 2 calc SR . .


_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 F1 2.030(5) . ?
Zn1 F1 2.030(5) 9 ?
Zn1 N1 2.163(5) 10 ?
Zn1 N1 2.163(5) 2 ?
Zn1 N1 2.163(5) 9 ?
Zn1 N1 2.163(5) . ?
I1 I2 2.809(4) . ?
I2 I1 2.809(4) 9_654 ?
Si1 F2 1.670(4) . ?
Si1 F2 1.670(4) 9_556 ?
Si1 F2 1.670(4) 10_556 ?
Si1 F2 1.670(4) 2 ?
Si1 F1 1.708(5) 9_556 ?
Si1 F1 1.708(5) . ?
O1 C4 1.223(9) . ?
N1 C1 1.292(6) 11 ?
N1 C1 1.292(6) . ?
N2 C4 1.386(8) . ?
N2 C4 1.386(8) 5 ?
N2 C3 1.451(9) . ?
C1 C2 1.374(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.335(7) . ?
C2 H2 0.9500 . ?
C3 C2 1.335(7) 11 ?
C4 C5 1.483(8) . ?
C5 C7 1.338(10) . ?
C5 C6 1.414(8) . ?
C6 C6 1.411(13) 9_655 ?
C6 C5 1.414(8) 5 ?
C7 C7 1.412(11) 13_655 ?
C7 H7 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
F1 Zn1 F1 180.0 . 9 ?
F1 Zn1 N1 90.0 . 10 ?
F1 Zn1 N1 90.0 9 10 ?
F1 Zn1 N1 90.0 . 2 ?
F1 Zn1 N1 90.0 9 2 ?
N1 Zn1 N1 180.0 10 2 ?
F1 Zn1 N1 90.0 . 9 ?
F1 Zn1 N1 90.0 9 9 ?
N1 Zn1 N1 90.0 10 9 ?
N1 Zn1 N1 90.0 2 9 ?
F1 Zn1 N1 90.0 . . ?
F1 Zn1 N1 90.0 9 . ?
N1 Zn1 N1 90.0 10 . ?
N1 Zn1 N1 90.0 2 . ?
N1 Zn1 N1 180.0 9 . ?
I1 I2 I1 180.0 9_654 . ?
F2 Si1 F2 180.0(3) . 9_556 ?
F2 Si1 F2 90.0 . 10_556 ?
F2 Si1 F2 90.0 9_556 10_556 ?
F2 Si1 F2 90.0 . 2 ?
F2 Si1 F2 90.0 9_556 2 ?
F2 Si1 F2 180.00(15) 10_556 2 ?
F2 Si1 F1 90.0 . 9_556 ?
F2 Si1 F1 90.0 9_556 9_556 ?
F2 Si1 F1 90.0 10_556 9_556 ?
F2 Si1 F1 90.0 2 9_556 ?
F2 Si1 F1 90.0 . . ?
F2 Si1 F1 90.0 9_556 . ?
F2 Si1 F1 90.0 10_556 . ?
F2 Si1 F1 90.0 2 . ?
F1 Si1 F1 180.0 9_556 . ?
Si1 F1 Zn1 180.0 . . ?
C1 N1 C1 115.5(6) 11 . ?
C1 N1 Zn1 122.2(3) 11 . ?
C1 N1 Zn1 122.2(3) . . ?
C4 N2 C4 125.7(7) . 5 ?
C4 N2 C3 117.2(3) . . ?
C4 N2 C3 117.2(3) 5 . ?
N1 C1 C2 124.3(5) . . ?
N1 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?
C3 C2 C1 119.1(5) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C2 117.7(7) 11 . ?
C2 C3 N2 121.2(4) 11 . ?
C2 C3 N2 121.2(4) . . ?
O1 C4 N2 120.7(6) . . ?
O1 C4 C5 121.9(7) . . ?
N2 C4 C5 117.4(6) . . ?
C7 C5 C6 120.6(6) . . ?
C7 C5 C4 120.8(6) . . ?
C6 C5 C4 118.6(6) . . ?
C6 C6 C5 118.8(4) 9_655 5 ?
C6 C6 C5 118.8(4) 9_655 . ?
C5 C6 C5 122.4(7) 5 . ?
C5 C7 C7 120.6(4) . 13_655 ?
C5 C7 H7 119.7 . . ?
C7 C7 H7 119.7 13_655 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F2 Si1 F1 Zn1 0(100) . . . . ?
F2 Si1 F1 Zn1 0.0 9_556 . . . ?
F2 Si1 F1 Zn1 0(100) 10_556 . . . ?
F2 Si1 F1 Zn1 0(100) 2 . . . ?
F1 Si1 F1 Zn1 0.0 9_556 . . . ?
F1 Zn1 F1 Si1 0.0 9 . . . ?
N1 Zn1 F1 Si1 0.0 10 . . . ?
N1 Zn1 F1 Si1 0.0 2 . . . ?
N1 Zn1 F1 Si1 0.0 9 . . . ?
N1 Zn1 F1 Si1 0.0 . . . . ?
F1 Zn1 N1 C1 0.0 . . . 11 ?
F1 Zn1 N1 C1 180.0 9 . . 11 ?
N1 Zn1 N1 C1 -90.0 10 . . 11 ?
N1 Zn1 N1 C1 90.0 2 . . 11 ?
N1 Zn1 N1 C1 0.0 9 . . 11 ?
F1 Zn1 N1 C1 180.0 . . . . ?
F1 Zn1 N1 C1 0.0 9 . . . ?
N1 Zn1 N1 C1 90.0 10 . . . ?
N1 Zn1 N1 C1 -90.0 2 . . . ?
N1 Zn1 N1 C1 0.0 9 . . . ?
C1 N1 C1 C2 0.0 11 . . . ?
Zn1 N1 C1 C2 180.0 . . . . ?
N1 C1 C2 C3 0.0 . . . . ?
C1 C2 C3 C2 0.0 . . . 11 ?
C1 C2 C3 N2 180.0 . . . . ?
C4 N2 C3 C2 -90.0 . . . 11 ?
C4 N2 C3 C2 90.0 5 . . 11 ?
C4 N2 C3 C2 90.0 . . . . ?
C4 N2 C3 C2 -90.0 5 . . . ?
C4 N2 C4 O1 180.0 5 . . . ?
C3 N2 C4 O1 0.0 . . . . ?
C4 N2 C4 C5 0.0 5 . . . ?
C3 N2 C4 C5 180.0 . . . . ?
O1 C4 C5 C7 0.0 . . . . ?
N2 C4 C5 C7 180.0 . . . . ?
O1 C4 C5 C6 180.0 . . . . ?
N2 C4 C5 C6 0.0 . . . . ?
C7 C5 C6 C6 0.0 . . . 9_655 ?
C4 C5 C6 C6 180.0 . . . 9_655 ?
C7 C5 C6 C5 180.0 . . . 5 ?
C4 C5 C6 C5 0.0 . . . 5 ?
C6 C5 C7 C7 0.0 . . . 13_655 ?
C4 C5 C7 C7 180.0 . . . 13_655 ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         2.043
_refine_diff_density_min         -1.407
_refine_diff_density_rms         0.183
_database_code_depnum_ccdc_archive 'CCDC 1025386'
