# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_d1429_a
_database_code_depnum_ccdc_archive 'CCDC 1422277'
_audit_update_record             
;
2015-09-03 deposited with the CCDC.
2015-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013

# start Validation Reply Form
_vrf_PLAT019_d1429_a             
;
PROBLEM: _diffrn_measured_fraction_theta_full/_max < 1.0      0.971 Why ? 
RESPONSE:  98.1\% of the data were collected to the required resolution.
The standard uncertainties of the geometric parameters and the good
R values indicate the structure is of very good precision.


;
# end Validation Reply Form


_chemical_name_systematic        
'bis(3,5-difluorophenoxy) silicon phthalocyanine'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H22 F4 N8 O2 Si'
_chemical_formula_sum            'C44 H22 F4 N8 O2 Si'
_chemical_formula_weight         798.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   8.4484(6)
_cell_length_b                   13.6023(9)
_cell_length_c                   15.2391(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.453(3)
_cell_angle_gamma                90
_cell_volume                     1736.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    147(2)
_cell_measurement_reflns_used    6440
_cell_measurement_theta_min      4.37
_cell_measurement_theta_max      66.32

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.258
_shelx_estimated_absorpt_T_min   0.769
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6983
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      147(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker ImuS'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11884
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.373
_diffrn_reflns_theta_max         66.519
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.953
_reflns_number_total             2992
_reflns_number_gt                2721
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+0.7593P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2992
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0792
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.5000 0.5000 0.5000 0.01604(14) Uani 1 2 d S . P . .
F1 F 0.66635(13) 0.72637(7) 0.20686(6) 0.0392(3) Uani 1 1 d . . . . .
F2 F 0.32304(12) 0.46817(7) 0.10455(6) 0.0394(2) Uani 1 1 d . . . . .
O1 O 0.56568(11) 0.46969(7) 0.40064(6) 0.0195(2) Uani 1 1 d . . . . .
N1 N 0.31801(13) 0.41629(8) 0.46910(7) 0.0184(2) Uani 1 1 d . . . . .
N2 N 0.12281(13) 0.53383(9) 0.40241(8) 0.0214(3) Uani 1 1 d . . . . .
N3 N 0.37832(13) 0.61014(8) 0.45235(7) 0.0176(2) Uani 1 1 d . . . . .
N4 N 0.57007(13) 0.74250(8) 0.48538(7) 0.0202(3) Uani 1 1 d . . . . .
C1 C 0.16904(16) 0.44489(10) 0.42925(9) 0.0191(3) Uani 1 1 d . . . . .
C2 C 0.22103(16) 0.60952(10) 0.41359(9) 0.0193(3) Uani 1 1 d . . . . .
C3 C 0.17140(16) 0.70810(11) 0.38739(9) 0.0213(3) Uani 1 1 d . . . . .
C4 C 0.02791(18) 0.74538(12) 0.34491(10) 0.0265(3) Uani 1 1 d . . . . .
H4A H -0.0599 0.7035 0.3261 0.032 Uiso 1 1 calc R U . . .
C5 C 0.01841(19) 0.84592(12) 0.33120(10) 0.0309(4) Uani 1 1 d . . . . .
H5A H -0.0778 0.8735 0.3022 0.037 Uiso 1 1 calc R U . . .
C6 C 0.14758(19) 0.90791(12) 0.35916(10) 0.0299(3) Uani 1 1 d . . . . .
H6A H 0.1369 0.9767 0.3492 0.036 Uiso 1 1 calc R U . . .
C7 C 0.29018(18) 0.87104(11) 0.40101(10) 0.0258(3) Uani 1 1 d . . . . .
H7A H 0.3778 0.9130 0.4201 0.031 Uiso 1 1 calc R U . . .
C8 C 0.30020(17) 0.76952(11) 0.41415(9) 0.0211(3) Uani 1 1 d . . . . .
C9 C 0.42841(16) 0.70706(10) 0.45400(9) 0.0185(3) Uani 1 1 d . . . . .
C10 C 0.68718(16) 0.68432(10) 0.51982(9) 0.0186(3) Uani 1 1 d . . . . .
C11 C 0.84560(16) 0.72065(11) 0.55171(9) 0.0203(3) Uani 1 1 d . . . . .
C12 C 0.91100(18) 0.81491(11) 0.55463(10) 0.0258(3) Uani 1 1 d . . . . .
H12A H 0.8499 0.8704 0.5327 0.031 Uiso 1 1 calc R U . . .
C13 C 1.06922(19) 0.82379(12) 0.59107(11) 0.0304(4) Uani 1 1 d . . . . .
H13A H 1.1175 0.8870 0.5949 0.037 Uiso 1 1 calc R U . . .
C14 C 1.15982(18) 0.74186(12) 0.62240(10) 0.0299(4) Uani 1 1 d . . . . .
H14A H 1.2682 0.7508 0.6467 0.036 Uiso 1 1 calc R U . . .
C15 C 1.09529(17) 0.64829(11) 0.61884(10) 0.0255(3) Uani 1 1 d . . . . .
H15A H 1.1568 0.5926 0.6398 0.031 Uiso 1 1 calc R U . . .
C16 C 0.93555(16) 0.63971(11) 0.58293(9) 0.0208(3) Uani 1 1 d . . . . .
C17 C 0.53896(16) 0.51373(10) 0.32087(9) 0.0185(3) Uani 1 1 d . . . . .
C18 C 0.61717(17) 0.60096(11) 0.30482(9) 0.0227(3) Uani 1 1 d . . . . .
H18A H 0.6865 0.6323 0.3505 0.027 Uiso 1 1 calc R U . . .
C19 C 0.59119(18) 0.64028(11) 0.22125(10) 0.0251(3) Uani 1 1 d . . . . .
C20 C 0.49481(18) 0.59853(11) 0.15163(10) 0.0268(3) Uani 1 1 d . . . . .
H20A H 0.4809 0.6268 0.0941 0.032 Uiso 1 1 calc R U . . .
C21 C 0.41979(18) 0.51275(11) 0.17113(10) 0.0256(3) Uani 1 1 d . . . . .
C22 C 0.43817(16) 0.46873(11) 0.25300(9) 0.0223(3) Uani 1 1 d . . . . .
H22A H 0.3838 0.4095 0.2630 0.027 Uiso 1 1 calc R U . . .


_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
Si1 O1 1.7287(9) 3_666 ?
Si1 O1 1.7287(9) . ?
Si1 N3 1.9066(11) 3_666 ?
Si1 N3 1.9066(11) . ?
Si1 N1 1.9220(11) 3_666 ?
Si1 N1 1.9221(11) . ?
F1 C19 1.3634(17) . ?
F2 C21 1.3602(17) . ?
O1 C17 1.3477(16) . ?
N1 C10 1.3803(18) 3_666 ?
N1 C1 1.3806(18) . ?
N2 C2 1.3194(18) . ?
N2 C1 1.3198(19) . ?
N3 C2 1.3824(18) . ?
N3 C9 1.3839(18) . ?
N4 C9 1.3210(18) . ?
N4 C10 1.3213(18) . ?
C1 C16 1.4481(19) 3_666 ?
C2 C3 1.446(2) . ?
C3 C8 1.390(2) . ?
C3 C4 1.394(2) . ?
C4 C5 1.384(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.401(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.382(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.396(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.447(2) . ?
C10 N1 1.3803(18) 3_666 ?
C10 C11 1.4501(19) . ?
C11 C16 1.386(2) . ?
C11 C12 1.395(2) . ?
C12 C13 1.385(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.400(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.383(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.394(2) . ?
C15 H15A 0.9500 . ?
C16 C1 1.4481(19) 3_666 ?
C17 C22 1.393(2) . ?
C17 C18 1.395(2) . ?
C18 C19 1.372(2) . ?
C18 H18A 0.9500 . ?
C19 C20 1.374(2) . ?
C20 C21 1.379(2) . ?
C20 H20A 0.9500 . ?
C21 C22 1.374(2) . ?
C22 H22A 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 Si1 O1 180.0 3_666 . ?
O1 Si1 N3 94.14(4) 3_666 3_666 ?
O1 Si1 N3 85.86(4) . 3_666 ?
O1 Si1 N3 85.86(4) 3_666 . ?
O1 Si1 N3 94.14(4) . . ?
N3 Si1 N3 180.0 3_666 . ?
O1 Si1 N1 88.94(4) 3_666 3_666 ?
O1 Si1 N1 91.06(4) . 3_666 ?
N3 Si1 N1 89.86(5) 3_666 3_666 ?
N3 Si1 N1 90.14(5) . 3_666 ?
O1 Si1 N1 91.06(4) 3_666 . ?
O1 Si1 N1 88.94(4) . . ?
N3 Si1 N1 90.14(5) 3_666 . ?
N3 Si1 N1 89.86(5) . . ?
N1 Si1 N1 180.0 3_666 . ?
C17 O1 Si1 130.46(8) . . ?
C10 N1 C1 106.96(11) 3_666 . ?
C10 N1 Si1 126.48(9) 3_666 . ?
C1 N1 Si1 126.54(9) . . ?
C2 N2 C1 121.29(12) . . ?
C2 N3 C9 106.76(11) . . ?
C2 N3 Si1 126.79(9) . . ?
C9 N3 Si1 126.38(9) . . ?
C9 N4 C10 121.45(12) . . ?
N2 C1 N1 127.65(12) . . ?
N2 C1 C16 122.52(13) . 3_666 ?
N1 C1 C16 109.80(12) . 3_666 ?
N2 C2 N3 127.84(13) . . ?
N2 C2 C3 122.21(12) . . ?
N3 C2 C3 109.92(12) . . ?
C8 C3 C4 121.20(14) . . ?
C8 C3 C2 106.77(12) . . ?
C4 C3 C2 132.02(14) . . ?
C5 C4 C3 117.35(15) . . ?
C5 C4 H4A 121.3 . . ?
C3 C4 H4A 121.3 . . ?
C4 C5 C6 121.41(15) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C7 C6 C5 121.32(14) . . ?
C7 C6 H6A 119.3 . . ?
C5 C6 H6A 119.3 . . ?
C6 C7 C8 117.26(15) . . ?
C6 C7 H7A 121.4 . . ?
C8 C7 H7A 121.4 . . ?
C3 C8 C7 121.44(14) . . ?
C3 C8 C9 106.56(12) . . ?
C7 C8 C9 132.00(14) . . ?
N4 C9 N3 127.94(13) . . ?
N4 C9 C8 122.11(13) . . ?
N3 C9 C8 109.95(12) . . ?
N4 C10 N1 127.47(12) . 3_666 ?
N4 C10 C11 122.69(13) . . ?
N1 C10 C11 109.84(12) 3_666 . ?
C16 C11 C12 121.46(13) . . ?
C16 C11 C10 106.59(12) . . ?
C12 C11 C10 131.96(14) . . ?
C13 C12 C11 116.80(14) . . ?
C13 C12 H12A 121.6 . . ?
C11 C12 H12A 121.6 . . ?
C12 C13 C14 121.59(14) . . ?
C12 C13 H13A 119.2 . . ?
C14 C13 H13A 119.2 . . ?
C15 C14 C13 121.59(14) . . ?
C15 C14 H14A 119.2 . . ?
C13 C14 H14A 119.2 . . ?
C14 C15 C16 116.69(14) . . ?
C14 C15 H15A 121.7 . . ?
C16 C15 H15A 121.7 . . ?
C11 C16 C15 121.87(13) . . ?
C11 C16 C1 106.79(12) . 3_666 ?
C15 C16 C1 131.34(14) . 3_666 ?
O1 C17 C22 119.28(13) . . ?
O1 C17 C18 120.56(12) . . ?
C22 C17 C18 120.08(13) . . ?
C19 C18 C17 118.15(13) . . ?
C19 C18 H18A 120.9 . . ?
C17 C18 H18A 120.9 . . ?
F1 C19 C18 117.53(13) . . ?
F1 C19 C20 118.20(13) . . ?
C18 C19 C20 124.26(14) . . ?
C19 C20 C21 115.24(13) . . ?
C19 C20 H20A 122.4 . . ?
C21 C20 H20A 122.4 . . ?
F2 C21 C22 117.98(14) . . ?
F2 C21 C20 117.72(13) . . ?
C22 C21 C20 124.29(14) . . ?
C21 C22 C17 117.95(14) . . ?
C21 C22 H22A 121.0 . . ?
C17 C22 H22A 121.0 . . ?

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.043

_shelxl_version_number           2013-4




####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_d1459_a
_database_code_depnum_ccdc_archive 'CCDC 1422278'
_audit_update_record             
;
2015-09-03 deposited with the CCDC.
2015-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013

# start Validation Reply Form
_vrf_PLAT019_d1459_a             
;
PROBLEM: _diffrn_measured_fraction_theta_full/_max < 1.0      0.973 Why ? 
RESPONSE:  Using CuKalpha radiation with the geometry of this 
diffractomter it is difficult to acheive 100% of the data to 66.505
degrees in theta. However, 96.7% of the data were collected to this
resolution and the precision of the structure is quite good as reflected
in the standard uncertainties on the geometric parameters and the 
values for the R-indicies as these crystal were very small and poorly
diffracting. 
;
# end Validation Reply Form

_chemical_name_systematic        
'bis(2,4,6-trifluorophenoxy) silicon phthalocyanine'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H20 F6 N8 O2 Si'
_chemical_formula_sum            'C44 H20 F6 N8 O2 Si'
_chemical_formula_weight         834.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   9.6397(13)
_cell_length_b                   19.771(3)
_cell_length_c                   10.0445(10)
_cell_angle_alpha                90
_cell_angle_beta                 118.661(8)
_cell_angle_gamma                90
_cell_volume                     1679.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    147(2)
_cell_measurement_reflns_used    1205
_cell_measurement_theta_min      4.47
_cell_measurement_theta_max      63.33

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.419
_shelx_estimated_absorpt_T_min   0.883
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5941
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      147(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9308
_diffrn_reflns_av_unetI/netI     0.0753
_diffrn_reflns_av_R_equivalents  0.0817
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.473
_diffrn_reflns_theta_max         66.292
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.941
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.941
_reflns_number_total             2847
_reflns_number_gt                1988
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0831P)²+2.0568P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0035(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2847
_refine_ls_number_parameters     278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.1755
_refine_ls_wR_factor_gt          0.1583
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.5000 0.5000 0.5000 0.0266(4) Uani 1 2 d S . P . .
F1 F 0.5058(3) 0.31649(15) 0.5612(3) 0.0542(8) Uani 1 1 d . . . . .
F2 F 0.2346(4) 0.26740(15) 0.8328(3) 0.0586(9) Uani 1 1 d . . . . .
F3 F 0.1593(3) 0.47552(14) 0.5849(3) 0.0454(7) Uani 1 1 d . . . . .
O1 O 0.3609(3) 0.43901(15) 0.4762(3) 0.0281(7) Uani 1 1 d . . . . .
N1 N 0.3490(4) 0.53268(18) 0.3055(3) 0.0268(8) Uani 1 1 d . . . . .
N2 N 0.4104(4) 0.46384(19) 0.1408(3) 0.0297(8) Uani 1 1 d . . . . .
N3 N 0.5844(4) 0.44020(18) 0.4067(3) 0.0283(8) Uani 1 1 d . . . . .
N4 N 0.8019(4) 0.38841(18) 0.6273(3) 0.0294(8) Uani 1 1 d . . . . .
C1 C 0.3276(5) 0.5096(2) 0.1662(4) 0.0279(10) Uani 1 1 d . . . . .
C2 C 0.5292(5) 0.4323(2) 0.2528(4) 0.0287(10) Uani 1 1 d . . . . .
C3 C 0.6211(5) 0.3811(2) 0.2274(4) 0.0284(10) Uani 1 1 d . . . . .
C4 C 0.6078(5) 0.3545(2) 0.0928(5) 0.0336(10) Uani 1 1 d . . . . .
H4A H 0.5297 0.3702 -0.0037 0.040 Uiso 1 1 calc R U . . .
C5 C 0.7126(5) 0.3049(2) 0.1066(5) 0.0363(11) Uani 1 1 d . . . . .
H5A H 0.7059 0.2851 0.0174 0.044 Uiso 1 1 calc R U . . .
C6 C 0.8298(5) 0.2823(2) 0.2486(5) 0.0344(10) Uani 1 1 d . . . . .
H6A H 0.9014 0.2481 0.2537 0.041 Uiso 1 1 calc R U . . .
C7 C 0.8431(5) 0.3091(2) 0.3820(5) 0.0345(10) Uani 1 1 d . . . . .
H7A H 0.9218 0.2938 0.4786 0.041 Uiso 1 1 calc R U . . .
C8 C 0.7361(5) 0.3591(2) 0.3678(4) 0.0293(10) Uani 1 1 d . . . . .
C9 C 0.7104(5) 0.3971(2) 0.4795(4) 0.0284(9) Uani 1 1 d . . . . .
C10 C 0.7717(5) 0.4215(2) 0.7257(4) 0.0290(10) Uani 1 1 d . . . . .
C11 C 0.8690(5) 0.4131(2) 0.8875(4) 0.0287(9) Uani 1 1 d . . . . .
C12 C 1.0030(5) 0.3753(2) 0.9761(4) 0.0315(10) Uani 1 1 d . . . . .
H12A H 1.0460 0.3454 0.9315 0.038 Uiso 1 1 calc R U . . .
C13 C 1.0723(5) 0.3827(2) 1.1326(4) 0.0351(11) Uani 1 1 d . . . . .
H13A H 1.1652 0.3578 1.1962 0.042 Uiso 1 1 calc R U . . .
C14 C 1.0064(5) 0.4268(2) 1.1987(4) 0.0352(11) Uani 1 1 d . . . . .
H14A H 1.0556 0.4305 1.3060 0.042 Uiso 1 1 calc R U . . .
C15 C 0.8747(5) 0.4638(2) 1.1123(4) 0.0325(10) Uani 1 1 d . . . . .
H15A H 0.8304 0.4931 1.1570 0.039 Uiso 1 1 calc R U . . .
C16 C 0.8073(5) 0.4572(2) 0.9559(4) 0.0282(9) Uani 1 1 d . . . . .
C17 C 0.4054(5) 0.3349(2) 0.6151(5) 0.0384(11) Uani 1 1 d . . . . .
C18 C 0.3758(6) 0.2895(3) 0.7009(5) 0.0450(12) Uani 1 1 d . . . . .
H18A H 0.4251 0.2464 0.7260 0.054 Uiso 1 1 calc R U . . .
C19 C 0.2690(6) 0.3103(3) 0.7497(5) 0.0416(12) Uani 1 1 d . . . . .
C20 C 0.1971(6) 0.3718(2) 0.7128(5) 0.0390(11) Uani 1 1 d . . . . .
H20A H 0.1241 0.3849 0.7463 0.047 Uiso 1 1 calc R U . . .
C21 C 0.2333(5) 0.4148(2) 0.6254(4) 0.0334(10) Uani 1 1 d . . . . .
C22 C 0.3389(5) 0.3985(2) 0.5736(4) 0.0302(10) 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
Si1 O1 1.733(3) . ?
Si1 O1 1.733(3) 3_666 ?
Si1 N1 1.904(3) 3_666 ?
Si1 N1 1.904(3) . ?
Si1 N3 1.915(3) . ?
Si1 N3 1.916(3) 3_666 ?
F1 C17 1.366(5) . ?
F2 C19 1.338(5) . ?
F3 C21 1.356(5) . ?
O1 C22 1.356(5) . ?
N1 C10 1.386(5) 3_666 ?
N1 C1 1.390(5) . ?
N2 C1 1.310(5) . ?
N2 C2 1.316(5) . ?
N3 C9 1.372(5) . ?
N3 C2 1.382(5) . ?
N4 C9 1.325(5) . ?
N4 C10 1.330(5) . ?
C1 C16 1.448(6) 3_666 ?
C2 C3 1.445(6) . ?
C3 C8 1.381(6) . ?
C3 C4 1.399(5) . ?
C4 C5 1.367(6) . ?
C4 H4A 0.9500 . ?
C5 C6 1.402(6) . ?
C5 H5A 0.9500 . ?
C6 C7 1.388(6) . ?
C6 H6A 0.9500 . ?
C7 C8 1.387(6) . ?
C7 H7A 0.9500 . ?
C8 C9 1.466(6) . ?
C10 N1 1.386(5) 3_666 ?
C10 C11 1.444(5) . ?
C11 C12 1.383(6) . ?
C11 C16 1.405(6) . ?
C12 C13 1.390(6) . ?
C12 H12A 0.9500 . ?
C13 C14 1.417(6) . ?
C13 H13A 0.9500 . ?
C14 C15 1.358(6) . ?
C14 H14A 0.9500 . ?
C15 C16 1.389(5) . ?
C15 H15A 0.9500 . ?
C16 C1 1.448(6) 3_666 ?
C17 C18 1.364(7) . ?
C17 C22 1.383(6) . ?
C18 C19 1.397(7) . ?
C18 H18A 0.9500 . ?
C19 C20 1.361(7) . ?
C20 C21 1.381(6) . ?
C20 H20A 0.9500 . ?
C21 C22 1.385(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
O1 Si1 O1 180.0 . 3_666 ?
O1 Si1 N1 93.75(13) . 3_666 ?
O1 Si1 N1 86.25(13) 3_666 3_666 ?
O1 Si1 N1 86.25(13) . . ?
O1 Si1 N1 93.75(13) 3_666 . ?
N1 Si1 N1 180.0 3_666 . ?
O1 Si1 N3 89.16(14) . . ?
O1 Si1 N3 90.84(14) 3_666 . ?
N1 Si1 N3 89.84(14) 3_666 . ?
N1 Si1 N3 90.16(13) . . ?
O1 Si1 N3 90.84(14) . 3_666 ?
O1 Si1 N3 89.16(14) 3_666 3_666 ?
N1 Si1 N3 90.16(13) 3_666 3_666 ?
N1 Si1 N3 89.84(14) . 3_666 ?
N3 Si1 N3 180.0 . 3_666 ?
C22 O1 Si1 133.6(2) . . ?
C10 N1 C1 106.5(3) 3_666 . ?
C10 N1 Si1 126.8(2) 3_666 . ?
C1 N1 Si1 126.4(3) . . ?
C1 N2 C2 121.5(3) . . ?
C9 N3 C2 107.0(3) . . ?
C9 N3 Si1 126.7(3) . . ?
C2 N3 Si1 126.3(3) . . ?
C9 N4 C10 120.2(4) . . ?
N2 C1 N1 127.8(4) . . ?
N2 C1 C16 122.1(3) . 3_666 ?
N1 C1 C16 110.1(4) . 3_666 ?
N2 C2 N3 127.8(4) . . ?
N2 C2 C3 122.5(3) . . ?
N3 C2 C3 109.7(3) . . ?
C8 C3 C4 121.7(4) . . ?
C8 C3 C2 107.4(3) . . ?
C4 C3 C2 130.9(4) . . ?
C5 C4 C3 116.9(4) . . ?
C5 C4 H4A 121.6 . . ?
C3 C4 H4A 121.6 . . ?
C4 C5 C6 121.8(4) . . ?
C4 C5 H5A 119.1 . . ?
C6 C5 H5A 119.1 . . ?
C7 C6 C5 121.2(4) . . ?
C7 C6 H6A 119.4 . . ?
C5 C6 H6A 119.4 . . ?
C8 C7 C6 116.9(4) . . ?
C8 C7 H7A 121.5 . . ?
C6 C7 H7A 121.5 . . ?
C3 C8 C7 121.5(4) . . ?
C3 C8 C9 105.8(4) . . ?
C7 C8 C9 132.6(4) . . ?
N4 C9 N3 128.4(4) . . ?
N4 C9 C8 121.6(4) . . ?
N3 C9 C8 110.0(3) . . ?
N4 C10 N1 127.8(3) . 3_666 ?
N4 C10 C11 121.6(4) . . ?
N1 C10 C11 110.6(3) 3_666 . ?
C12 C11 C16 120.2(4) . . ?
C12 C11 C10 133.5(4) . . ?
C16 C11 C10 106.2(4) . . ?
C11 C12 C13 117.7(4) . . ?
C11 C12 H12A 121.1 . . ?
C13 C12 H12A 121.1 . . ?
C12 C13 C14 120.9(4) . . ?
C12 C13 H13A 119.6 . . ?
C14 C13 H13A 119.6 . . ?
C15 C14 C13 121.6(4) . . ?
C15 C14 H14A 119.2 . . ?
C13 C14 H14A 119.2 . . ?
C14 C15 C16 117.3(4) . . ?
C14 C15 H15A 121.4 . . ?
C16 C15 H15A 121.4 . . ?
C15 C16 C11 122.2(4) . . ?
C15 C16 C1 131.1(4) . 3_666 ?
C11 C16 C1 106.6(3) . 3_666 ?
C18 C17 F1 118.6(4) . . ?
C18 C17 C22 125.5(4) . . ?
F1 C17 C22 115.9(4) . . ?
C17 C18 C19 116.2(5) . . ?
C17 C18 H18A 121.9 . . ?
C19 C18 H18A 121.9 . . ?
F2 C19 C20 119.3(4) . . ?
F2 C19 C18 118.6(4) . . ?
C20 C19 C18 122.1(4) . . ?
C19 C20 C21 118.1(4) . . ?
C19 C20 H20A 120.9 . . ?
C21 C20 H20A 120.9 . . ?
F3 C21 C20 118.6(4) . . ?
F3 C21 C22 117.9(4) . . ?
C20 C21 C22 123.5(4) . . ?
O1 C22 C17 123.0(4) . . ?
O1 C22 C21 122.1(4) . . ?
C17 C22 C21 114.6(4) . . ?

_refine_diff_density_max         0.440
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.082

_shelxl_version_number           2013-4




####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_d1416
_database_code_depnum_ccdc_archive 'CCDC 1422279'
_audit_update_record             
;
2015-09-03 deposited with the CCDC.
2015-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013

# start Validation Reply Form
_vrf_PLAT019_d1416               
;
PROBLEM: Check _diffrn_measured_fraction_theta_full/_max       0.974       
RESPONSE: 97.5% of the data were measured to the required thata max. 
For CuKalpha radiation and the geometry of this type of diffractomer 
we feel this is acceptable. The good precision of the structure is 
reflected in the R-factors and the standard unceratinties of the 
geometric parameters.
;
# end Validation Reply Form

_chemical_name_systematic        
'bis(3,4,5-trifluorophenoxy) silicon phthalocyanine'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H20 F6 N8 O2 Si'
_chemical_formula_sum            'C44 H20 F6 N8 O2 Si'
_chemical_formula_weight         834.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_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                   10.2098(6)
_cell_length_b                   17.6974(13)
_cell_length_c                   10.7963(7)
_cell_angle_alpha                90
_cell_angle_beta                 117.669(3)
_cell_angle_gamma                90
_cell_volume                     1727.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    147(2)
_cell_measurement_reflns_used    5231
_cell_measurement_theta_min      4.93
_cell_measurement_theta_max      66.42

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.380
_shelx_estimated_absorpt_T_min   0.922
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6872
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS (Sheldrick, 19960'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      147(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_diffrn_measurement_device_type  'Bruker KAPPA APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11544
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.930
_diffrn_reflns_theta_max         66.546
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.950
_reflns_number_total             2962
_reflns_number_gt                2622
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0426P)²+0.8938P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2962
_refine_ls_number_parameters     277
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0850
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.5000 0.5000 0.5000 0.01532(15) Uani 1 2 d S . P . .
F1 F 0.32741(13) 0.57861(6) -0.08255(10) 0.0387(3) Uani 1 1 d . . . . .
F2 F 0.17951(12) 0.70866(7) -0.09689(11) 0.0402(3) Uani 1 1 d . . . . .
F3 F 0.20173(11) 0.77100(6) 0.13886(11) 0.0352(3) Uani 1 1 d . . . . .
O1 O 0.52465(11) 0.57590(6) 0.41141(11) 0.0189(3) Uani 1 1 d . . . . .
N1 N 0.68657(13) 0.46164(8) 0.52718(13) 0.0172(3) Uani 1 1 d . . . . .
N2 N 0.60848(14) 0.38231(8) 0.32185(14) 0.0192(3) Uani 1 1 d . . . . .
N3 N 0.40044(14) 0.44262(8) 0.33202(13) 0.0167(3) Uani 1 1 d . . . . .
N4 N 0.14464(14) 0.47735(8) 0.25579(13) 0.0199(3) Uani 1 1 d . . . . .
C1 C 0.82441(16) 0.47911(9) 0.63523(16) 0.0175(3) Uani 1 1 d . . . . .
C2 C 0.93790(17) 0.44273(9) 0.61209(17) 0.0192(3) Uani 1 1 d . . . . .
C3 C 1.09186(17) 0.44474(10) 0.68779(18) 0.0232(4) Uani 1 1 d . . . . .
H3A H 1.1410 0.4719 0.7732 0.028 Uiso 1 1 calc R U . . .
C4 C 1.16926(18) 0.40537(10) 0.63249(19) 0.0262(4) Uani 1 1 d . . . . .
H4A H 1.2742 0.4047 0.6819 0.031 Uiso 1 1 calc R U . . .
C5 C 1.09758(18) 0.36645(10) 0.50591(18) 0.0252(4) Uani 1 1 d . . . . .
H5A H 1.1550 0.3410 0.4704 0.030 Uiso 1 1 calc R U . . .
C6 C 0.94486(18) 0.36404(10) 0.43089(18) 0.0229(4) Uani 1 1 d . . . . .
H6A H 0.8960 0.3374 0.3449 0.027 Uiso 1 1 calc R U . . .
C7 C 0.86631(17) 0.40249(9) 0.48762(16) 0.0189(3) Uani 1 1 d . . . . .
C8 C 0.70972(17) 0.41429(9) 0.43760(16) 0.0178(3) Uani 1 1 d . . . . .
C9 C 0.46608(17) 0.39584(9) 0.27476(16) 0.0176(3) Uani 1 1 d . . . . .
C10 C 0.35523(17) 0.36338(9) 0.14521(17) 0.0198(3) Uani 1 1 d . . . . .
C11 C 0.36425(19) 0.31291(10) 0.05091(17) 0.0236(4) Uani 1 1 d . . . . .
H11A H 0.4566 0.2929 0.0651 0.028 Uiso 1 1 calc R U . . .
C12 C 0.23352(19) 0.29288(10) -0.06454(18) 0.0263(4) Uani 1 1 d . . . . .
H12A H 0.2361 0.2584 -0.1308 0.032 Uiso 1 1 calc R U . . .
C13 C 0.09750(19) 0.32255(10) -0.08558(18) 0.0260(4) Uani 1 1 d . . . . .
H13A H 0.0096 0.3075 -0.1656 0.031 Uiso 1 1 calc R U . . .
C14 C 0.08832(18) 0.37324(10) 0.00741(17) 0.0244(4) Uani 1 1 d . . . . .
H14A H -0.0038 0.3939 -0.0076 0.029 Uiso 1 1 calc R U . . .
C15 C 0.22013(17) 0.39284(9) 0.12435(16) 0.0196(3) Uani 1 1 d . . . . .
C16 C 0.25061(17) 0.44155(9) 0.24189(16) 0.0182(3) Uani 1 1 d . . . . .
C17 C 0.43476(16) 0.60643(9) 0.28505(16) 0.0181(3) Uani 1 1 d . . . . .
C18 C 0.42468(18) 0.57481(10) 0.16233(17) 0.0219(4) Uani 1 1 d . . . . .
H18A H 0.4769 0.5297 0.1660 0.026 Uiso 1 1 calc R U . . .
C19 C 0.33865(19) 0.60939(10) 0.03638(17) 0.0253(4) Uani 1 1 d . . . . .
C20 C 0.26319(18) 0.67521(10) 0.02717(17) 0.0261(4) Uani 1 1 d . . . . .
C21 C 0.27554(18) 0.70590(10) 0.14935(18) 0.0238(4) Uani 1 1 d . . . . .
C22 C 0.35885(17) 0.67327(10) 0.27791(17) 0.0215(4) Uani 1 1 d . . . . .
H22A H 0.3647 0.6957 0.3603 0.026 Uiso 1 1 calc R U . . .


_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
Si1 O1 1.7337(11) 3_666 ?
Si1 O1 1.7337(11) . ?
Si1 N3 1.9083(13) . ?
Si1 N3 1.9083(13) 3_666 ?
Si1 N1 1.9121(13) . ?
Si1 N1 1.9121(13) 3_666 ?
F1 C19 1.3497(19) . ?
F2 C20 1.3460(19) . ?
F3 C21 1.352(2) . ?
O1 C17 1.3538(19) . ?
N1 C8 1.381(2) . ?
N1 C1 1.3828(19) . ?
N2 C9 1.320(2) . ?
N2 C8 1.323(2) . ?
N3 C9 1.379(2) . ?
N3 C16 1.380(2) . ?
N4 C1 1.316(2) 3_666 ?
N4 C16 1.321(2) . ?
C1 N4 1.316(2) 3_666 ?
C1 C2 1.445(2) . ?
C2 C7 1.391(2) . ?
C2 C3 1.395(2) . ?
C3 C4 1.380(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.396(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.384(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.392(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.445(2) . ?
C9 C10 1.448(2) . ?
C10 C11 1.389(2) . ?
C10 C15 1.392(2) . ?
C11 C12 1.384(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.401(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.382(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.396(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.443(2) . ?
C17 C22 1.397(2) . ?
C17 C18 1.397(2) . ?
C18 C19 1.373(2) . ?
C18 H18A 0.9500 . ?
C19 C20 1.375(3) . ?
C20 C21 1.377(2) . ?
C21 C22 1.374(2) . ?
C22 H22A 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 Si1 O1 180.0 3_666 . ?
O1 Si1 N3 87.84(5) 3_666 . ?
O1 Si1 N3 92.16(5) . . ?
O1 Si1 N3 92.17(5) 3_666 3_666 ?
O1 Si1 N3 87.83(5) . 3_666 ?
N3 Si1 N3 180.0 . 3_666 ?
O1 Si1 N1 91.70(5) 3_666 . ?
O1 Si1 N1 88.29(5) . . ?
N3 Si1 N1 90.57(5) . . ?
N3 Si1 N1 89.43(5) 3_666 . ?
O1 Si1 N1 88.30(5) 3_666 3_666 ?
O1 Si1 N1 91.70(5) . 3_666 ?
N3 Si1 N1 89.43(5) . 3_666 ?
N3 Si1 N1 90.57(5) 3_666 3_666 ?
N1 Si1 N1 180.0 . 3_666 ?
C17 O1 Si1 131.37(10) . . ?
C8 N1 C1 106.76(12) . . ?
C8 N1 Si1 126.19(10) . . ?
C1 N1 Si1 126.95(11) . . ?
C9 N2 C8 121.58(14) . . ?
C9 N3 C16 106.62(13) . . ?
C9 N3 Si1 126.18(10) . . ?
C16 N3 Si1 127.17(11) . . ?
C1 N4 C16 120.86(13) 3_666 . ?
N4 C1 N1 127.79(14) 3_666 . ?
N4 C1 C2 122.44(14) 3_666 . ?
N1 C1 C2 109.77(14) . . ?
C7 C2 C3 121.51(15) . . ?
C7 C2 C1 106.93(13) . . ?
C3 C2 C1 131.53(16) . . ?
C4 C3 C2 116.70(16) . . ?
C4 C3 H3A 121.6 . . ?
C2 C3 H3A 121.6 . . ?
C3 C4 C5 121.83(15) . . ?
C3 C4 H4A 119.1 . . ?
C5 C4 H4A 119.1 . . ?
C6 C5 C4 121.60(15) . . ?
C6 C5 H5A 119.2 . . ?
C4 C5 H5A 119.2 . . ?
C5 C6 C7 116.75(16) . . ?
C5 C6 H6A 121.6 . . ?
C7 C6 H6A 121.6 . . ?
C2 C7 C6 121.58(15) . . ?
C2 C7 C8 106.31(14) . . ?
C6 C7 C8 132.03(15) . . ?
N2 C8 N1 127.48(14) . . ?
N2 C8 C7 122.31(14) . . ?
N1 C8 C7 110.21(13) . . ?
N2 C9 N3 127.87(14) . . ?
N2 C9 C10 121.79(14) . . ?
N3 C9 C10 110.29(13) . . ?
C11 C10 C15 121.35(15) . . ?
C11 C10 C9 132.45(15) . . ?
C15 C10 C9 106.20(14) . . ?
C12 C11 C10 117.41(16) . . ?
C12 C11 H11A 121.3 . . ?
C10 C11 H11A 121.3 . . ?
C11 C12 C13 121.25(16) . . ?
C11 C12 H12A 119.4 . . ?
C13 C12 H12A 119.4 . . ?
C14 C13 C12 121.47(15) . . ?
C14 C13 H13A 119.3 . . ?
C12 C13 H13A 119.3 . . ?
C13 C14 C15 117.16(16) . . ?
C13 C14 H14A 121.4 . . ?
C15 C14 H14A 121.4 . . ?
C10 C15 C14 121.35(15) . . ?
C10 C15 C16 106.78(14) . . ?
C14 C15 C16 131.87(15) . . ?
N4 C16 N3 127.69(14) . . ?
N4 C16 C15 122.19(14) . . ?
N3 C16 C15 110.11(13) . . ?
O1 C17 C22 119.53(14) . . ?
O1 C17 C18 120.84(15) . . ?
C22 C17 C18 119.49(15) . . ?
C19 C18 C17 119.47(16) . . ?
C19 C18 H18A 120.3 . . ?
C17 C18 H18A 120.3 . . ?
F1 C19 C18 119.66(16) . . ?
F1 C19 C20 118.43(15) . . ?
C18 C19 C20 121.91(16) . . ?
F2 C20 C19 121.34(16) . . ?
F2 C20 C21 120.88(16) . . ?
C19 C20 C21 117.78(15) . . ?
F3 C21 C22 120.15(15) . . ?
F3 C21 C20 117.14(15) . . ?
C22 C21 C20 122.71(16) . . ?
C21 C22 C17 118.64(15) . . ?
C21 C22 H22A 120.7 . . ?
C17 C22 H22A 120.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 Si1 O1 C17 38.98(14) . . . . ?
N3 Si1 O1 C17 -141.02(14) 3_666 . . . ?
N1 Si1 O1 C17 129.48(14) . . . . ?
N1 Si1 O1 C17 -50.52(14) 3_666 . . . ?
C8 N1 C1 N4 179.94(16) . . . 3_666 ?
Si1 N1 C1 N4 3.3(2) . . . 3_666 ?
C8 N1 C1 C2 0.93(17) . . . . ?
Si1 N1 C1 C2 -175.69(11) . . . . ?
N4 C1 C2 C7 -179.21(15) 3_666 . . . ?
N1 C1 C2 C7 -0.13(18) . . . . ?
N4 C1 C2 C3 -1.3(3) 3_666 . . . ?
N1 C1 C2 C3 177.77(17) . . . . ?
C7 C2 C3 C4 0.5(2) . . . . ?
C1 C2 C3 C4 -177.16(17) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C3 C2 C7 C6 -1.7(2) . . . . ?
C1 C2 C7 C6 176.42(15) . . . . ?
C3 C2 C7 C8 -178.83(15) . . . . ?
C1 C2 C7 C8 -0.68(17) . . . . ?
C5 C6 C7 C2 1.4(2) . . . . ?
C5 C6 C7 C8 177.60(17) . . . . ?
C9 N2 C8 N1 2.9(3) . . . . ?
C9 N2 C8 C7 -177.47(15) . . . . ?
C1 N1 C8 N2 178.34(16) . . . . ?
Si1 N1 C8 N2 -5.0(2) . . . . ?
C1 N1 C8 C7 -1.37(17) . . . . ?
Si1 N1 C8 C7 175.28(10) . . . . ?
C2 C7 C8 N2 -178.44(15) . . . . ?
C6 C7 C8 N2 4.9(3) . . . . ?
C2 C7 C8 N1 1.29(18) . . . . ?
C6 C7 C8 N1 -175.38(17) . . . . ?
C8 N2 C9 N3 0.4(3) . . . . ?
C8 N2 C9 C10 177.49(15) . . . . ?
C16 N3 C9 N2 176.76(16) . . . . ?
Si1 N3 C9 N2 -1.3(2) . . . . ?
C16 N3 C9 C10 -0.57(17) . . . . ?
Si1 N3 C9 C10 -178.58(11) . . . . ?
N2 C9 C10 C11 3.6(3) . . . . ?
N3 C9 C10 C11 -178.88(17) . . . . ?
N2 C9 C10 C15 -176.61(15) . . . . ?
N3 C9 C10 C15 0.90(18) . . . . ?
C15 C10 C11 C12 -0.2(3) . . . . ?
C9 C10 C11 C12 179.59(17) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
C11 C10 C15 C14 -0.4(3) . . . . ?
C9 C10 C15 C14 179.80(15) . . . . ?
C11 C10 C15 C16 178.97(15) . . . . ?
C9 C10 C15 C16 -0.84(18) . . . . ?
C13 C14 C15 C10 0.9(3) . . . . ?
C13 C14 C15 C16 -178.27(17) . . . . ?
C1 N4 C16 N3 0.5(3) 3_666 . . . ?
C1 N4 C16 C15 179.38(15) 3_666 . . . ?
C9 N3 C16 N4 178.98(16) . . . . ?
Si1 N3 C16 N4 -3.0(2) . . . . ?
C9 N3 C16 C15 0.03(18) . . . . ?
Si1 N3 C16 C15 178.01(11) . . . . ?
C10 C15 C16 N4 -178.49(15) . . . . ?
C14 C15 C16 N4 0.8(3) . . . . ?
C10 C15 C16 N3 0.53(18) . . . . ?
C14 C15 C16 N3 179.80(17) . . . . ?
Si1 O1 C17 C22 102.55(16) . . . . ?
Si1 O1 C17 C18 -81.82(18) . . . . ?
O1 C17 C18 C19 -176.52(14) . . . . ?
C22 C17 C18 C19 -0.9(2) . . . . ?
C17 C18 C19 F1 -179.33(14) . . . . ?
C17 C18 C19 C20 1.0(3) . . . . ?
F1 C19 C20 F2 0.1(2) . . . . ?
C18 C19 C20 F2 179.84(15) . . . . ?
F1 C19 C20 C21 179.91(15) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
F2 C20 C21 F3 -0.8(2) . . . . ?
C19 C20 C21 F3 179.45(15) . . . . ?
F2 C20 C21 C22 179.50(15) . . . . ?
C19 C20 C21 C22 -0.3(3) . . . . ?
F3 C21 C22 C17 -179.40(14) . . . . ?
C20 C21 C22 C17 0.3(3) . . . . ?
O1 C17 C22 C21 175.95(14) . . . . ?
C18 C17 C22 C21 0.3(2) . . . . ?

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4




####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_d1419
_database_code_depnum_ccdc_archive 'CCDC 1422280'
_audit_update_record             
;
2015-09-03 deposited with the CCDC.
2015-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013

# start Validation Reply Form
_vrf_PLAT019_d1419               
;
PROBLEM: _diffrn_measured_fraction_theta_full/_max < 1.0      0.977 Why ? 
RESPONSE:  96.7% of the data were measured to the required thata max. 
For CuKalpha radiation, the geometry of this type of diffractomer 
and the space group, we feel this is acceptable. The good precision of the 
structure is  reflected in the R-factors and the standard unceratinties of 
the geometric parameters.
;
# end Validation Reply Form

_chemical_name_systematic        
'bis(2,3,4,6-tetrafluorophenoxy) silicon phthalocyanine'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H18 F8 N8 O2 Si'
_chemical_formula_sum            'C44 H18 F8 N8 O2 Si'
_chemical_formula_weight         870.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4175(8)
_cell_length_b                   10.1685(9)
_cell_length_c                   11.5194(10)
_cell_angle_alpha                72.562(3)
_cell_angle_beta                 69.559(3)
_cell_angle_gamma                81.366(3)
_cell_volume                     880.30(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    147(2)
_cell_measurement_reflns_used    9282
_cell_measurement_theta_min      4.25
_cell_measurement_theta_max      66.47

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.025
_exptl_absorpt_coefficient_mu    1.467
_shelx_estimated_absorpt_T_min   0.558
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6617
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      147(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker Imus with multi-layer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11039
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.250
_diffrn_reflns_theta_max         66.464
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.945
_reflns_number_total             2991
_reflns_number_gt                2906
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0432P)²+0.4555P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2991
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0825
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.5000 0.5000 0.5000 0.01274(14) Uani 1 2 d S . P . .
F1 F 0.43456(11) 0.12782(8) 0.67923(8) 0.0264(2) Uani 1 1 d . . . . .
F2 F 0.65487(15) -0.08960(9) 0.67115(9) 0.0414(3) Uani 1 1 d . . . . .
F3 F 0.91265(13) 0.09959(10) 0.22619(9) 0.0410(3) Uani 1 1 d . . . . .
F4 F 0.69736(11) 0.32043(8) 0.23491(8) 0.0255(2) Uani 1 1 d . . . . .
O1 O 0.46376(11) 0.35097(9) 0.46573(9) 0.0163(2) Uani 1 1 d . . . . .
N1 N 0.13266(14) 0.64963(11) 0.45316(11) 0.0158(2) Uani 1 1 d . . . . .
N2 N 0.26848(14) 0.50368(11) 0.60531(11) 0.0148(2) Uani 1 1 d . . . . .
N3 N 0.29088(14) 0.36957(11) 0.81304(11) 0.0169(3) Uani 1 1 d . . . . .
N4 N 0.56447(14) 0.39055(11) 0.64454(11) 0.0144(2) Uani 1 1 d . . . . .
C1 C 0.13181(17) 0.57427(13) 0.56886(13) 0.0149(3) Uani 1 1 d . . . . .
C2 C -0.02021(17) 0.55940(14) 0.67903(13) 0.0158(3) Uani 1 1 d . . . . .
C3 C -0.18642(17) 0.61250(14) 0.69142(14) 0.0181(3) Uani 1 1 d . . . . .
H3A H -0.2182 0.6659 0.6190 0.022 Uiso 1 1 calc R U . . .
C4 C -0.30259(18) 0.58361(15) 0.81410(14) 0.0214(3) Uani 1 1 d . . . . .
H4A H -0.4167 0.6187 0.8265 0.026 Uiso 1 1 calc R U . . .
C5 C -0.25546(18) 0.50334(15) 0.92090(14) 0.0218(3) Uani 1 1 d . . . . .
H5A H -0.3381 0.4868 1.0040 0.026 Uiso 1 1 calc R U . . .
C6 C -0.09160(18) 0.44785(15) 0.90789(13) 0.0194(3) Uani 1 1 d . . . . .
H6A H -0.0606 0.3917 0.9798 0.023 Uiso 1 1 calc R U . . .
C7 C 0.02580(17) 0.47812(14) 0.78442(13) 0.0168(3) Uani 1 1 d . . . . .
C8 C 0.20551(17) 0.44357(13) 0.73668(13) 0.0155(3) Uani 1 1 d . . . . .
C9 C 0.45629(17) 0.34569(13) 0.76916(12) 0.0153(3) Uani 1 1 d . . . . .
C10 C 0.55069(17) 0.26112(13) 0.85097(13) 0.0167(3) Uani 1 1 d . . . . .
C11 C 0.50017(19) 0.19362(15) 0.98148(13) 0.0209(3) Uani 1 1 d . . . . .
H11A H 0.3852 0.1984 1.0345 0.025 Uiso 1 1 calc R U . . .
C12 C 0.6247(2) 0.11918(16) 1.03077(14) 0.0267(3) Uani 1 1 d . . . . .
H12A H 0.5950 0.0724 1.1197 0.032 Uiso 1 1 calc R U . . .
C13 C 0.7941(2) 0.11143(17) 0.95196(15) 0.0290(4) Uani 1 1 d . . . . .
H13A H 0.8763 0.0589 0.9888 0.035 Uiso 1 1 calc R U . . .
C14 C 0.84475(19) 0.17816(15) 0.82214(14) 0.0224(3) Uani 1 1 d . . . . .
H14A H 0.9596 0.1727 0.7691 0.027 Uiso 1 1 calc R U . . .
C15 C 0.71923(18) 0.25384(14) 0.77283(13) 0.0169(3) Uani 1 1 d . . . . .
C16 C 0.72514(17) 0.33558(13) 0.64500(13) 0.0149(3) Uani 1 1 d . . . . .
C17 C 0.56835(17) 0.23776(14) 0.45979(13) 0.0170(3) Uani 1 1 d . . . . .
C18 C 0.55823(19) 0.12573(15) 0.56749(14) 0.0206(3) Uani 1 1 d . . . . .
C19 C 0.6700(2) 0.01239(15) 0.56191(15) 0.0273(3) Uani 1 1 d . . . . .
C20 C 0.7940(2) 0.00034(16) 0.44918(16) 0.0308(4) Uani 1 1 d . . . . .
H20A H 0.8723 -0.0772 0.4464 0.037 Uiso 1 1 calc R U . . .
C21 C 0.7984(2) 0.10660(16) 0.34064(15) 0.0265(3) Uani 1 1 d . . . . .
C22 C 0.68861(18) 0.22151(14) 0.34486(13) 0.0200(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
Si1 O1 1.7683(9) . ?
Si1 O1 1.7683(9) 2_666 ?
Si1 N2 1.9039(11) 2_666 ?
Si1 N2 1.9039(11) . ?
Si1 N4 1.9091(11) . ?
Si1 N4 1.9092(11) 2_666 ?
F1 C18 1.3472(17) . ?
F2 C19 1.3493(17) . ?
F3 C21 1.3486(18) . ?
F4 C22 1.3472(16) . ?
O1 C17 1.3438(16) . ?
N1 C16 1.3193(18) 2_666 ?
N1 C1 1.3215(18) . ?
N2 C1 1.3870(17) . ?
N2 C8 1.3883(17) . ?
N3 C9 1.3166(18) . ?
N3 C8 1.3187(18) . ?
N4 C9 1.3846(17) . ?
N4 C16 1.3849(17) . ?
C1 C2 1.4421(19) . ?
C2 C7 1.3921(19) . ?
C2 C3 1.396(2) . ?
C3 C4 1.383(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.407(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.384(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.393(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.4454(19) . ?
C9 C10 1.4461(19) . ?
C10 C11 1.391(2) . ?
C10 C15 1.395(2) . ?
C11 C12 1.384(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.403(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.383(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.394(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.4455(19) . ?
C16 N1 1.3193(18) 2_666 ?
C17 C22 1.396(2) . ?
C17 C18 1.397(2) . ?
C18 C19 1.377(2) . ?
C19 C20 1.378(2) . ?
C20 C21 1.379(2) . ?
C20 H20A 0.9500 . ?
C21 C22 1.378(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Si1 O1 180.0 . 2_666 ?
O1 Si1 N2 91.44(4) . 2_666 ?
O1 Si1 N2 88.56(4) 2_666 2_666 ?
O1 Si1 N2 88.56(4) . . ?
O1 Si1 N2 91.44(4) 2_666 . ?
N2 Si1 N2 180.0 2_666 . ?
O1 Si1 N4 91.45(4) . . ?
O1 Si1 N4 88.55(4) 2_666 . ?
N2 Si1 N4 89.37(5) 2_666 . ?
N2 Si1 N4 90.63(5) . . ?
O1 Si1 N4 88.55(4) . 2_666 ?
O1 Si1 N4 91.45(4) 2_666 2_666 ?
N2 Si1 N4 90.63(5) 2_666 2_666 ?
N2 Si1 N4 89.37(5) . 2_666 ?
N4 Si1 N4 180.00(6) . 2_666 ?
C17 O1 Si1 126.36(8) . . ?
C16 N1 C1 120.66(12) 2_666 . ?
C1 N2 C8 106.40(11) . . ?
C1 N2 Si1 127.23(9) . . ?
C8 N2 Si1 126.23(9) . . ?
C9 N3 C8 121.46(12) . . ?
C9 N4 C16 106.67(11) . . ?
C9 N4 Si1 126.03(9) . . ?
C16 N4 Si1 127.24(9) . . ?
N1 C1 N2 127.71(12) . . ?
N1 C1 C2 122.12(12) . . ?
N2 C1 C2 110.14(11) . . ?
C7 C2 C3 121.75(13) . . ?
C7 C2 C1 106.79(12) . . ?
C3 C2 C1 131.45(13) . . ?
C4 C3 C2 116.81(13) . . ?
C4 C3 H3A 121.6 . . ?
C2 C3 H3A 121.6 . . ?
C3 C4 C5 121.43(13) . . ?
C3 C4 H4A 119.3 . . ?
C5 C4 H4A 119.3 . . ?
C6 C5 C4 121.64(13) . . ?
C6 C5 H5A 119.2 . . ?
C4 C5 H5A 119.2 . . ?
C5 C6 C7 116.89(13) . . ?
C5 C6 H6A 121.6 . . ?
C7 C6 H6A 121.6 . . ?
C2 C7 C6 121.46(13) . . ?
C2 C7 C8 106.63(12) . . ?
C6 C7 C8 131.88(13) . . ?
N3 C8 N2 127.67(12) . . ?
N3 C8 C7 122.24(12) . . ?
N2 C8 C7 110.04(11) . . ?
N3 C9 N4 127.96(12) . . ?
N3 C9 C10 122.03(12) . . ?
N4 C9 C10 109.99(11) . . ?
C11 C10 C15 121.62(13) . . ?
C11 C10 C9 131.70(13) . . ?
C15 C10 C9 106.68(12) . . ?
C12 C11 C10 117.07(14) . . ?
C12 C11 H11A 121.5 . . ?
C10 C11 H11A 121.5 . . ?
C11 C12 C13 121.27(14) . . ?
C11 C12 H12A 119.4 . . ?
C13 C12 H12A 119.4 . . ?
C14 C13 C12 121.82(14) . . ?
C14 C13 H13A 119.1 . . ?
C12 C13 H13A 119.1 . . ?
C13 C14 C15 116.82(14) . . ?
C13 C14 H14A 121.6 . . ?
C15 C14 H14A 121.6 . . ?
C14 C15 C10 121.40(13) . . ?
C14 C15 C16 132.04(13) . . ?
C10 C15 C16 106.55(12) . . ?
N1 C16 N4 127.67(12) 2_666 . ?
N1 C16 C15 122.22(12) 2_666 . ?
N4 C16 C15 110.10(11) . . ?
O1 C17 C22 122.36(12) . . ?
O1 C17 C18 121.98(12) . . ?
C22 C17 C18 115.60(13) . . ?
F1 C18 C19 119.12(13) . . ?
F1 C18 C17 119.20(12) . . ?
C19 C18 C17 121.67(13) . . ?
F2 C19 C18 117.99(14) . . ?
F2 C19 C20 119.88(14) . . ?
C18 C19 C20 122.13(14) . . ?
C19 C20 C21 116.61(14) . . ?
C19 C20 H20A 121.7 . . ?
C21 C20 H20A 121.7 . . ?
F3 C21 C22 118.20(14) . . ?
F3 C21 C20 119.84(14) . . ?
C22 C21 C20 121.96(14) . . ?
F4 C22 C21 119.00(13) . . ?
F4 C22 C17 119.21(12) . . ?
C21 C22 C17 121.79(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Si1 O1 C17 41.71(11) 2_666 . . . ?
N2 Si1 O1 C17 -138.29(11) . . . . ?
N4 Si1 O1 C17 -47.70(11) . . . . ?
N4 Si1 O1 C17 132.30(11) 2_666 . . . ?
C16 N1 C1 N2 0.4(2) 2_666 . . . ?
C16 N1 C1 C2 178.03(12) 2_666 . . . ?
C8 N2 C1 N1 178.25(13) . . . . ?
Si1 N2 C1 N1 2.4(2) . . . . ?
C8 N2 C1 C2 0.34(14) . . . . ?
Si1 N2 C1 C2 -175.48(9) . . . . ?
N1 C1 C2 C7 -177.96(12) . . . . ?
N2 C1 C2 C7 0.08(15) . . . . ?
N1 C1 C2 C3 0.7(2) . . . . ?
N2 C1 C2 C3 178.73(13) . . . . ?
C7 C2 C3 C4 1.7(2) . . . . ?
C1 C2 C3 C4 -176.80(13) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
C4 C5 C6 C7 1.6(2) . . . . ?
C3 C2 C7 C6 -1.1(2) . . . . ?
C1 C2 C7 C6 177.69(12) . . . . ?
C3 C2 C7 C8 -179.26(12) . . . . ?
C1 C2 C7 C8 -0.45(14) . . . . ?
C5 C6 C7 C2 -0.6(2) . . . . ?
C5 C6 C7 C8 177.06(14) . . . . ?
C9 N3 C8 N2 1.1(2) . . . . ?
C9 N3 C8 C7 -176.05(12) . . . . ?
C1 N2 C8 N3 -178.09(13) . . . . ?
Si1 N2 C8 N3 -2.2(2) . . . . ?
C1 N2 C8 C7 -0.63(14) . . . . ?
Si1 N2 C8 C7 175.24(9) . . . . ?
C2 C7 C8 N3 178.31(12) . . . . ?
C6 C7 C8 N3 0.4(2) . . . . ?
C2 C7 C8 N2 0.69(15) . . . . ?
C6 C7 C8 N2 -177.19(14) . . . . ?
C8 N3 C9 N4 0.4(2) . . . . ?
C8 N3 C9 C10 -178.00(12) . . . . ?
C16 N4 C9 N3 -178.06(13) . . . . ?
Si1 N4 C9 N3 -0.6(2) . . . . ?
C16 N4 C9 C10 0.47(14) . . . . ?
Si1 N4 C9 C10 177.90(9) . . . . ?
N3 C9 C10 C11 -1.6(2) . . . . ?
N4 C9 C10 C11 179.79(14) . . . . ?
N3 C9 C10 C15 177.88(12) . . . . ?
N4 C9 C10 C15 -0.77(15) . . . . ?
C15 C10 C11 C12 0.3(2) . . . . ?
C9 C10 C11 C12 179.64(14) . . . . ?
C10 C11 C12 C13 -0.5(2) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C13 C14 C15 C10 -0.3(2) . . . . ?
C13 C14 C15 C16 179.62(14) . . . . ?
C11 C10 C15 C14 0.1(2) . . . . ?
C9 C10 C15 C14 -179.37(13) . . . . ?
C11 C10 C15 C16 -179.76(12) . . . . ?
C9 C10 C15 C16 0.72(15) . . . . ?
C9 N4 C16 N1 179.39(13) . . . 2_666 ?
Si1 N4 C16 N1 2.0(2) . . . 2_666 ?
C9 N4 C16 C15 -0.01(14) . . . . ?
Si1 N4 C16 C15 -177.39(9) . . . . ?
C14 C15 C16 N1 0.2(2) . . . 2_666 ?
C10 C15 C16 N1 -179.91(12) . . . 2_666 ?
C14 C15 C16 N4 179.64(14) . . . . ?
C10 C15 C16 N4 -0.46(15) . . . . ?
Si1 O1 C17 C22 -92.75(14) . . . . ?
Si1 O1 C17 C18 90.31(15) . . . . ?
O1 C17 C18 F1 3.5(2) . . . . ?
C22 C17 C18 F1 -173.64(12) . . . . ?
O1 C17 C18 C19 -177.40(13) . . . . ?
C22 C17 C18 C19 5.5(2) . . . . ?
F1 C18 C19 F2 -2.9(2) . . . . ?
C17 C18 C19 F2 178.03(13) . . . . ?
F1 C18 C19 C20 176.58(14) . . . . ?
C17 C18 C19 C20 -2.5(2) . . . . ?
F2 C19 C20 C21 178.00(14) . . . . ?
C18 C19 C20 C21 -1.4(2) . . . . ?
C19 C20 C21 F3 -177.83(14) . . . . ?
C19 C20 C21 C22 2.2(2) . . . . ?
F3 C21 C22 F4 1.3(2) . . . . ?
C20 C21 C22 F4 -178.72(14) . . . . ?
F3 C21 C22 C17 -178.99(13) . . . . ?
C20 C21 C22 C17 1.0(2) . . . . ?
O1 C17 C22 F4 -2.1(2) . . . . ?
C18 C17 C22 F4 174.99(12) . . . . ?
O1 C17 C22 C21 178.15(13) . . . . ?
C18 C17 C22 C21 -4.7(2) . . . . ?

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.058

_shelxl_version_number           2013-4




