# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_x15169
_database_code_depnum_ccdc_archive 'CCDC 1418455'
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2014). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2015-08-12 deposited with the CCDC.
2016-03-10 downloaded from the CCDC.
;

_audit_creation_method           'SHELXL-2014/7 and CIFFIX'

_shelx_SHELXL_version_number     2014/7

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H F8 N S'
_chemical_formula_sum            'C12 H F8 N S'
_chemical_formula_weight         343.20

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'
S S 0.3331 0.5567 '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                   3.7431(2)
_cell_length_b                   14.0603(8)
_cell_length_c                   21.1275(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.387(3)
_cell_angle_gamma                90
_cell_volume                     1109.98(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    7141
_cell_measurement_theta_min      3.78
_cell_measurement_theta_max      68.14

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.054
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    3.678
_shelx_estimated_absorpt_T_min   0.527
_shelx_estimated_absorpt_T_max   0.898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.611
_exptl_absorpt_correction_T_max  0.915
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by x-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the x-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;

_exptl_special_details           
; 
The crystal was mounted using polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
The crystals underwent a destructive phase transition when cooled to 90K. 
Visual inspection of crystal integrity and diffraction quality vs temperature 
established a safe temperature for data collection of -93° C. 
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus rotating anode'
_diffrn_measurement_device_type  'Bruker X8 Proteum diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 5.6
_diffrn_reflns_number            12956
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.778
_diffrn_reflns_theta_max         68.253
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.984

_reflns_number_total             2007
_reflns_number_gt                1770
_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-AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker-AXS, 2006)'
_computing_data_reduction        'APEX2 (Bruker-AXS, 2006)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'

_refine_special_details          
; 
Refinement progress was checked using Platon (Spek, 2009) and by 
an R-tensor (Parkin, 2000). The final model was further checked 
with the IUCr utility checkCIF. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0368P)²+1.6697P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2007
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1033
_refine_ls_wR_factor_gt          0.1003
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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
N1 N 0.5956(8) 0.24681(18) 0.64750(12) 0.0348(6) Uani 1 1 d . . . . .
H1N H 0.532(9) 0.202(3) 0.6661(17) 0.042 Uiso 1 1 d . U . . .
S1 S 0.85853(17) 0.42090(5) 0.57399(3) 0.02754(19) Uani 1 1 d . . . . .
C1 C 0.5895(7) 0.3336(2) 0.67923(13) 0.0266(6) Uani 1 1 d . . . . .
C2 C 0.4764(8) 0.3368(2) 0.74038(13) 0.0298(6) Uani 1 1 d . . . . .
C3 C 0.4760(8) 0.4208(2) 0.77435(13) 0.0320(6) Uani 1 1 d . . . . .
C4 C 0.5875(8) 0.5033(2) 0.74653(14) 0.0310(6) Uani 1 1 d . . . . .
C5 C 0.6973(7) 0.5012(2) 0.68544(13) 0.0272(6) Uani 1 1 d . . . . .
C6 C 0.7010(7) 0.41734(19) 0.65093(13) 0.0247(6) Uani 1 1 d . . . . .
C7 C 0.6567(7) 0.31606(19) 0.54336(12) 0.0240(6) Uani 1 1 d . . . . .
C8 C 0.6108(7) 0.3062(2) 0.47822(13) 0.0259(6) Uani 1 1 d . . . . .
C9 C 0.4682(7) 0.2250(2) 0.45027(13) 0.0289(6) Uani 1 1 d . . . . .
C10 C 0.3674(8) 0.1514(2) 0.48810(14) 0.0302(6) Uani 1 1 d . . . . .
C11 C 0.4070(7) 0.1606(2) 0.55311(13) 0.0283(6) Uani 1 1 d . . . . .
C12 C 0.5527(7) 0.24143(19) 0.58151(12) 0.0260(6) Uani 1 1 d . . . . .
F1 F 0.3632(5) 0.25634(13) 0.76715(8) 0.0429(5) Uani 1 1 d . . . . .
F2 F 0.3631(5) 0.42233(14) 0.83298(8) 0.0442(5) Uani 1 1 d . . . . .
F3 F 0.5888(6) 0.58515(13) 0.77922(9) 0.0465(5) Uani 1 1 d . . . . .
F4 F 0.8132(5) 0.58172(12) 0.65992(8) 0.0398(4) Uani 1 1 d . . . . .
F5 F 0.7160(5) 0.37690(12) 0.44094(8) 0.0371(4) Uani 1 1 d . . . . .
F6 F 0.4262(5) 0.21836(13) 0.38700(8) 0.0443(5) Uani 1 1 d . . . . .
F7 F 0.2266(5) 0.07219(12) 0.46235(9) 0.0429(5) Uani 1 1 d . . . . .
F8 F 0.3021(5) 0.08941(12) 0.59007(8) 0.0428(5) 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
N1 C1 1.393(4) . ?
N1 C12 1.396(4) . ?
N1 H1N 0.79(4) . ?
S1 C7 1.762(3) . ?
S1 C6 1.762(3) . ?
C1 C2 1.384(4) . ?
C1 C6 1.395(4) . ?
C2 F1 1.344(3) . ?
C2 C3 1.383(4) . ?
C3 F2 1.332(3) . ?
C3 C4 1.376(4) . ?
C4 F3 1.342(3) . ?
C4 C5 1.378(4) . ?
C5 F4 1.337(3) . ?
C5 C6 1.387(4) . ?
C7 C8 1.384(4) . ?
C7 C12 1.393(4) . ?
C8 F5 1.342(3) . ?
C8 C9 1.378(4) . ?
C9 F6 1.340(3) . ?
C9 C10 1.374(4) . ?
C10 F7 1.334(3) . ?
C10 C11 1.379(4) . ?
C11 F8 1.342(3) . ?
C11 C12 1.382(4) . ?

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
C1 N1 C12 121.6(2) . . ?
C1 N1 H1N 117(3) . . ?
C12 N1 H1N 116(3) . . ?
C7 S1 C6 98.94(12) . . ?
C2 C1 N1 119.5(3) . . ?
C2 C1 C6 119.3(3) . . ?
N1 C1 C6 121.3(3) . . ?
F1 C2 C3 119.4(2) . . ?
F1 C2 C1 119.2(2) . . ?
C3 C2 C1 121.4(3) . . ?
F2 C3 C4 120.3(3) . . ?
F2 C3 C2 120.4(3) . . ?
C4 C3 C2 119.3(3) . . ?
F3 C4 C3 119.6(3) . . ?
F3 C4 C5 120.5(3) . . ?
C3 C4 C5 119.8(3) . . ?
F4 C5 C4 118.8(2) . . ?
F4 C5 C6 119.6(3) . . ?
C4 C5 C6 121.6(3) . . ?
C5 C6 C1 118.7(3) . . ?
C5 C6 S1 118.4(2) . . ?
C1 C6 S1 123.0(2) . . ?
C8 C7 C12 118.5(2) . . ?
C8 C7 S1 118.3(2) . . ?
C12 C7 S1 123.1(2) . . ?
F5 C8 C9 118.8(2) . . ?
F5 C8 C7 119.1(2) . . ?
C9 C8 C7 122.1(2) . . ?
F6 C9 C10 120.5(3) . . ?
F6 C9 C8 120.3(3) . . ?
C10 C9 C8 119.2(3) . . ?
F7 C10 C9 120.5(3) . . ?
F7 C10 C11 120.1(3) . . ?
C9 C10 C11 119.5(3) . . ?
F8 C11 C10 119.5(2) . . ?
F8 C11 C12 118.8(2) . . ?
C10 C11 C12 121.7(3) . . ?
C11 C12 C7 119.0(2) . . ?
C11 C12 N1 119.8(2) . . ?
C7 C12 N1 121.2(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N1 C1 C2 151.7(3) . . . . ?
C12 N1 C1 C6 -29.4(4) . . . . ?
N1 C1 C2 F1 -2.2(4) . . . . ?
C6 C1 C2 F1 178.9(2) . . . . ?
N1 C1 C2 C3 178.1(3) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
F1 C2 C3 F2 -0.3(4) . . . . ?
C1 C2 C3 F2 179.4(3) . . . . ?
F1 C2 C3 C4 -179.1(3) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
F2 C3 C4 F3 1.3(4) . . . . ?
C2 C3 C4 F3 -179.8(3) . . . . ?
F2 C3 C4 C5 -178.8(3) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
F3 C4 C5 F4 1.6(4) . . . . ?
C3 C4 C5 F4 -178.3(2) . . . . ?
F3 C4 C5 C6 179.5(2) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
F4 C5 C6 C1 178.0(2) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
F4 C5 C6 S1 -0.3(3) . . . . ?
C4 C5 C6 S1 -178.1(2) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
N1 C1 C6 C5 -178.4(2) . . . . ?
C2 C1 C6 S1 178.7(2) . . . . ?
N1 C1 C6 S1 -0.3(4) . . . . ?
C7 S1 C6 C5 -159.3(2) . . . . ?
C7 S1 C6 C1 22.5(2) . . . . ?
C6 S1 C7 C8 159.1(2) . . . . ?
C6 S1 C7 C12 -23.2(2) . . . . ?
C12 C7 C8 F5 -178.8(2) . . . . ?
S1 C7 C8 F5 -1.0(3) . . . . ?
C12 C7 C8 C9 -0.4(4) . . . . ?
S1 C7 C8 C9 177.4(2) . . . . ?
F5 C8 C9 F6 -2.0(4) . . . . ?
C7 C8 C9 F6 179.6(2) . . . . ?
F5 C8 C9 C10 178.5(2) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
F6 C9 C10 F7 0.1(4) . . . . ?
C8 C9 C10 F7 179.6(3) . . . . ?
F6 C9 C10 C11 -178.8(2) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
F7 C10 C11 F8 -0.2(4) . . . . ?
C9 C10 C11 F8 178.7(2) . . . . ?
F7 C10 C11 C12 179.8(2) . . . . ?
C9 C10 C11 C12 -1.3(4) . . . . ?
F8 C11 C12 C7 -179.0(2) . . . . ?
C10 C11 C12 C7 1.0(4) . . . . ?
F8 C11 C12 N1 1.5(4) . . . . ?
C10 C11 C12 N1 -178.5(3) . . . . ?
C8 C7 C12 C11 -0.2(4) . . . . ?
S1 C7 C12 C11 -177.9(2) . . . . ?
C8 C7 C12 N1 179.4(2) . . . . ?
S1 C7 C12 N1 1.7(4) . . . . ?
C1 N1 C12 C11 -151.8(3) . . . . ?
C1 N1 C12 C7 28.6(4) . . . . ?

_refine_diff_density_max         0.248
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.061



####################################################################### 
# 
# 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_x15312
_database_code_depnum_ccdc_archive 'CCDC 1418456'
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2014). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2015-08-12 deposited with the CCDC.
2016-03-10 downloaded from the CCDC.
;

_audit_creation_method           'SHELXL-2014/7 and CIFFIX'

_shelx_SHELXL_version_number     2014/7

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H5 F8 N S'
_chemical_formula_sum            'C14 H5 F8 N S'
_chemical_formula_weight         371.25

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'
S S 0.3331 0.5567 '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                   15.9072(11)
_cell_length_b                   5.9576(4)
_cell_length_c                   16.081(1)
_cell_angle_alpha                90
_cell_angle_beta                 115.262(3)
_cell_angle_gamma                90
_cell_volume                     1378.23(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    8511
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      67.94

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.789
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    3.015
_shelx_estimated_absorpt_T_min   0.557
_shelx_estimated_absorpt_T_max   0.773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.695
_exptl_absorpt_correction_T_max  0.889
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by x-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the x-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;

_exptl_special_details           
; 
The crystal was mounted using polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
The crystals degraded visibly when cooled to 90K. Visual inspection of crystal 
integrity and diffraction quality vs temperature established a safe temperature 
for data collection of -23° C. 
;

_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus rotating anode'
_diffrn_measurement_device_type  'Bruker X8 Proteum diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 5.6
_diffrn_reflns_number            15924
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.272
_diffrn_reflns_theta_max         68.343
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.989

_reflns_number_total             2484
_reflns_number_gt                2064
_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-AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker-AXS, 2006)'
_computing_data_reduction        'APEX2 (Bruker-AXS, 2006)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'

_refine_special_details          
; 
Refinement progress was checked using Platon (Spek, 2009) and by 
an R-tensor (Parkin, 2000). The final model was further checked 
with the IUCr utility checkCIF. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0506P)²+0.8010P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2484
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1158
_refine_ls_wR_factor_gt          0.1085
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
S1 S 0.62810(5) 0.77154(11) 0.44492(5) 0.0612(2) Uani 1 1 d . . . . .
N1 N 0.73188(13) 0.3186(3) 0.48972(13) 0.0476(5) Uani 1 1 d . . . . .
C1 C 0.68836(15) 0.3829(4) 0.54599(15) 0.0429(5) Uani 1 1 d . . . . .
C2 C 0.69347(16) 0.2458(4) 0.61783(16) 0.0465(5) Uani 1 1 d . . . . .
C3 C 0.65443(17) 0.3045(4) 0.67633(16) 0.0500(6) Uani 1 1 d . . . . .
C4 C 0.60646(16) 0.5040(5) 0.66277(17) 0.0524(6) Uani 1 1 d . . . . .
C5 C 0.59653(16) 0.6363(4) 0.58945(18) 0.0500(6) Uani 1 1 d . . . . .
C6 C 0.63745(16) 0.5816(4) 0.53203(16) 0.0460(5) Uani 1 1 d . . . . .
C7 C 0.63794(17) 0.5784(4) 0.36672(17) 0.0484(6) Uani 1 1 d . . . . .
C8 C 0.59516(17) 0.6282(5) 0.27428(18) 0.0543(6) Uani 1 1 d . . . . .
C9 C 0.60156(18) 0.4885(5) 0.20959(17) 0.0589(7) Uani 1 1 d . . . . .
C10 C 0.65015(19) 0.2921(5) 0.23762(18) 0.0569(7) Uani 1 1 d . . . . .
C11 C 0.69232(17) 0.2387(4) 0.32976(18) 0.0513(6) Uani 1 1 d . . . . .
C12 C 0.68824(16) 0.3795(4) 0.39632(16) 0.0459(5) Uani 1 1 d . . . . .
C13 C 0.83355(18) 0.2893(6) 0.5325(2) 0.0700(8) Uani 1 1 d . . . . .
H13A H 0.8518 0.1991 0.4919 0.084 Uiso 1 1 calc R U . . .
H13B H 0.8524 0.2082 0.5907 0.084 Uiso 1 1 calc R U . . .
C14 C 0.8823(3) 0.5112(10) 0.5501(3) 0.129(2) Uani 1 1 d . . . . .
H14A H 0.8580 0.5992 0.4940 0.194 Uiso 1 1 calc R U . . .
H14B H 0.9484 0.4872 0.5701 0.194 Uiso 1 1 calc R U . . .
H14C H 0.8721 0.5909 0.5975 0.194 Uiso 1 1 calc R U . . .
F1 F 0.73786(11) 0.0472(2) 0.6325(1) 0.0590(4) Uani 1 1 d . . . . .
F2 F 0.66276(12) 0.1692(3) 0.7457(1) 0.0676(4) Uani 1 1 d . . . . .
F3 F 0.57014(11) 0.5660(3) 0.72058(11) 0.0694(5) Uani 1 1 d . . . . .
F4 F 0.54791(11) 0.8284(3) 0.57628(11) 0.0663(4) Uani 1 1 d . . . . .
F5 F 0.54669(12) 0.8208(3) 0.24664(11) 0.0719(5) Uani 1 1 d . . . . .
F6 F 0.55954(13) 0.5399(4) 0.11989(11) 0.0818(6) Uani 1 1 d . . . . .
F7 F 0.65674(13) 0.1513(3) 0.17586(11) 0.0771(5) Uani 1 1 d . . . . .
F8 F 0.73770(11) 0.0420(3) 0.35303(11) 0.0625(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C6 1.757(2) . ?
S1 C7 1.760(3) . ?
N1 C1 1.407(3) . ?
N1 C12 1.407(3) . ?
N1 C13 1.473(3) . ?
C1 C2 1.389(3) . ?
C1 C6 1.398(3) . ?
C2 F1 1.346(3) . ?
C2 C3 1.375(4) . ?
C3 F2 1.336(3) . ?
C3 C4 1.379(4) . ?
C4 F3 1.339(3) . ?
C4 C5 1.370(4) . ?
C5 F4 1.346(3) . ?
C5 C6 1.377(4) . ?
C7 C8 1.377(4) . ?
C7 C12 1.395(3) . ?
C8 F5 1.348(3) . ?
C8 C9 1.370(4) . ?
C9 F6 1.341(3) . ?
C9 C10 1.368(4) . ?
C10 F7 1.338(3) . ?
C10 C11 1.378(4) . ?
C11 F8 1.343(3) . ?
C11 C12 1.383(4) . ?
C13 C14 1.498(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 S1 C7 98.37(12) . . ?
C1 N1 C12 117.54(19) . . ?
C1 N1 C13 118.4(2) . . ?
C12 N1 C13 118.2(2) . . ?
C2 C1 C6 117.1(2) . . ?
C2 C1 N1 120.3(2) . . ?
C6 C1 N1 122.5(2) . . ?
F1 C2 C3 117.4(2) . . ?
F1 C2 C1 120.2(2) . . ?
C3 C2 C1 122.4(2) . . ?
F2 C3 C2 120.3(2) . . ?
F2 C3 C4 120.2(2) . . ?
C2 C3 C4 119.5(2) . . ?
F3 C4 C5 120.9(2) . . ?
F3 C4 C3 120.1(2) . . ?
C5 C4 C3 119.0(2) . . ?
F4 C5 C4 118.2(2) . . ?
F4 C5 C6 120.0(2) . . ?
C4 C5 C6 121.8(2) . . ?
C5 C6 C1 120.0(2) . . ?
C5 C6 S1 118.61(19) . . ?
C1 C6 S1 121.32(19) . . ?
C8 C7 C12 119.9(2) . . ?
C8 C7 S1 118.5(2) . . ?
C12 C7 S1 121.64(19) . . ?
F5 C8 C9 119.0(2) . . ?
F5 C8 C7 119.3(2) . . ?
C9 C8 C7 121.8(3) . . ?
F6 C9 C10 120.1(3) . . ?
F6 C9 C8 120.9(3) . . ?
C10 C9 C8 118.9(2) . . ?
F7 C10 C9 120.3(2) . . ?
F7 C10 C11 119.8(3) . . ?
C9 C10 C11 119.9(2) . . ?
F8 C11 C10 117.3(2) . . ?
F8 C11 C12 120.7(2) . . ?
C10 C11 C12 122.0(2) . . ?
C11 C12 C7 117.4(2) . . ?
C11 C12 N1 120.3(2) . . ?
C7 C12 N1 122.2(2) . . ?
N1 C13 C14 111.1(3) . . ?
N1 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
N1 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C12 N1 C1 C2 145.9(2) . . . . ?
C13 N1 C1 C2 -61.6(3) . . . . ?
C12 N1 C1 C6 -33.0(3) . . . . ?
C13 N1 C1 C6 119.5(3) . . . . ?
C6 C1 C2 F1 177.02(19) . . . . ?
N1 C1 C2 F1 -1.9(3) . . . . ?
C6 C1 C2 C3 -3.0(3) . . . . ?
N1 C1 C2 C3 178.0(2) . . . . ?
F1 C2 C3 F2 1.3(3) . . . . ?
C1 C2 C3 F2 -178.6(2) . . . . ?
F1 C2 C3 C4 -178.6(2) . . . . ?
C1 C2 C3 C4 1.5(4) . . . . ?
F2 C3 C4 F3 1.8(3) . . . . ?
C2 C3 C4 F3 -178.3(2) . . . . ?
F2 C3 C4 C5 -178.0(2) . . . . ?
C2 C3 C4 C5 1.9(3) . . . . ?
F3 C4 C5 F4 -1.1(3) . . . . ?
C3 C4 C5 F4 178.7(2) . . . . ?
F3 C4 C5 C6 176.5(2) . . . . ?
C3 C4 C5 C6 -3.6(4) . . . . ?
F4 C5 C6 C1 179.6(2) . . . . ?
C4 C5 C6 C1 2.1(4) . . . . ?
F4 C5 C6 S1 2.2(3) . . . . ?
C4 C5 C6 S1 -175.36(19) . . . . ?
C2 C1 C6 C5 1.3(3) . . . . ?
N1 C1 C6 C5 -179.8(2) . . . . ?
C2 C1 C6 S1 178.60(17) . . . . ?
N1 C1 C6 S1 -2.5(3) . . . . ?
C7 S1 C6 C5 -153.3(2) . . . . ?
C7 S1 C6 C1 29.3(2) . . . . ?
C6 S1 C7 C8 151.5(2) . . . . ?
C6 S1 C7 C12 -29.0(2) . . . . ?
C12 C7 C8 F5 179.9(2) . . . . ?
S1 C7 C8 F5 -0.6(3) . . . . ?
C12 C7 C8 C9 -1.0(4) . . . . ?
S1 C7 C8 C9 178.5(2) . . . . ?
F5 C8 C9 F6 -0.8(4) . . . . ?
C7 C8 C9 F6 -179.9(2) . . . . ?
F5 C8 C9 C10 -179.5(2) . . . . ?
C7 C8 C9 C10 1.4(4) . . . . ?
F6 C9 C10 F7 0.6(4) . . . . ?
C8 C9 C10 F7 179.3(2) . . . . ?
F6 C9 C10 C11 -179.3(2) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
F7 C10 C11 F8 -0.9(4) . . . . ?
C9 C10 C11 F8 178.9(2) . . . . ?
F7 C10 C11 C12 179.4(2) . . . . ?
C9 C10 C11 C12 -0.7(4) . . . . ?
F8 C11 C12 C7 -178.5(2) . . . . ?
C10 C11 C12 C7 1.2(4) . . . . ?
F8 C11 C12 N1 0.1(3) . . . . ?
C10 C11 C12 N1 179.7(2) . . . . ?
C8 C7 C12 C11 -0.3(3) . . . . ?
S1 C7 C12 C11 -179.75(18) . . . . ?
C8 C7 C12 N1 -178.8(2) . . . . ?
S1 C7 C12 N1 1.7(3) . . . . ?
C1 N1 C12 C11 -145.1(2) . . . . ?
C13 N1 C12 C11 62.3(3) . . . . ?
C1 N1 C12 C7 33.4(3) . . . . ?
C13 N1 C12 C7 -119.2(3) . . . . ?
C1 N1 C13 C14 -77.7(3) . . . . ?
C12 N1 C13 C14 74.7(3) . . . . ?

_refine_diff_density_max         0.439
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.046



