# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_171207_fpt_o
_database_code_depnum_ccdc_archive 'CCDC 1839025'
_audit_update_record             
;
2018-04-23 deposited with the CCDC.
2018-05-31 downloaded from the CCDC.
;
_audit_creation_date             2017-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 F2 O2 S2'
_chemical_formula_sum            'C16 H12 F2 O2 S2'
_chemical_formula_weight         338.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   5.5646(6)
_cell_length_b                   6.9441(8)
_cell_length_c                   18.902(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.039(12)
_cell_angle_gamma                90
_cell_volume                     723.22(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1412
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.2899
_cell_measurement_theta_min      3.1227
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.871
_exptl_absorpt_coefficient_mu    0.394
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4341
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_min         3.129
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -43.00   32.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   82.0000  162.0000 75

#__ type_ start__ end____ width___ exp.time_
  2 omega  -89.00   19.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -77.0000   30.0000 108

#__ type_ start__ end____ width___ exp.time_
  3 omega  -12.00   83.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   38.0000  -30.0000 95
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0849732000
_diffrn_orient_matrix_UB_12      -0.0762612000
_diffrn_orient_matrix_UB_13      -0.0066228000
_diffrn_orient_matrix_UB_21      -0.0512797000
_diffrn_orient_matrix_UB_22      0.0451494000
_diffrn_orient_matrix_UB_23      -0.0322472000
_diffrn_orient_matrix_UB_31      0.0820705000
_diffrn_orient_matrix_UB_32      -0.0507383000
_diffrn_orient_matrix_UB_33      -0.0187424000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1052
_reflns_number_total             1326
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0449
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0454P)²+0.6891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1151
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.87928(14) 0.36755(12) 0.69599(4) 0.0361(3) Uani 1 1 d . . . . .
F1 F 0.7303(3) 0.1706(2) 0.47265(8) 0.0288(4) Uani 1 1 d . . . . .
O1 O 0.3882(3) 0.3033(3) 0.37282(9) 0.0241(5) Uani 1 1 d . . . . .
C1 C 1.1403(6) 0.2406(4) 0.71533(17) 0.0365(8) Uani 1 1 d . . . . .
H1 H 1.211257 0.208324 0.762493 0.044 Uiso 1 1 calc R . . . .
C2 C 1.2358(5) 0.1906(4) 0.65633(17) 0.0349(7) Uani 1 1 d . . . . .
H2 H 1.382931 0.120332 0.657869 0.042 Uiso 1 1 calc R . . . .
C3 C 1.0969(5) 0.2523(4) 0.59171(14) 0.0214(6) Uani 1 1 d . . . . .
H3 H 1.139058 0.229242 0.545452 0.026 Uiso 1 1 calc R . . . .
C4 C 0.8880(5) 0.3523(4) 0.60527(14) 0.0232(6) Uani 1 1 d . . . . .
C5 C 0.6911(5) 0.4285(4) 0.55247(14) 0.0208(6) Uani 1 1 d . . . . .
C6 C 0.6201(5) 0.3379(4) 0.48725(14) 0.0216(6) Uani 1 1 d . . . . .
C7 C 0.4381(5) 0.4038(4) 0.43583(13) 0.0209(6) Uani 1 1 d . . . . .
C8 C 0.1991(6) 0.1629(4) 0.37483(16) 0.0352(7) Uani 1 1 d . . . . .
H8A H 0.167357 0.097109 0.328593 0.053 Uiso 1 1 calc GR . . . .
H8B H 0.050853 0.227400 0.384818 0.053 Uiso 1 1 calc GR . . . .
H8C H 0.250283 0.068422 0.412459 0.053 Uiso 1 1 calc GR . . . .


_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 C1 1.695(3) . ?
S1 C4 1.726(3) . ?
F1 C6 1.360(3) . ?
O1 C7 1.375(3) . ?
O1 C8 1.439(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.346(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.417(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.408(4) . ?
C4 C5 1.474(4) . ?
C5 C6 1.391(4) . ?
C5 C7 1.402(4) 3_666 ?
C6 C7 1.380(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C4 92.29(14) . . ?
C7 O1 C8 112.4(2) . . ?
S1 C1 H1 123.8 . . ?
C2 C1 S1 112.4(2) . . ?
C2 C1 H1 123.8 . . ?
C1 C2 H2 123.1 . . ?
C1 C2 C3 113.9(3) . . ?
C3 C2 H2 123.1 . . ?
C2 C3 H3 124.5 . . ?
C4 C3 C2 110.9(3) . . ?
C4 C3 H3 124.5 . . ?
C3 C4 S1 110.48(19) . . ?
C3 C4 C5 127.5(2) . . ?
C5 C4 S1 122.0(2) . . ?
C6 C5 C4 122.0(2) . . ?
C6 C5 C7 115.3(2) . 3_666 ?
C7 C5 C4 122.7(2) 3_666 . ?
F1 C6 C5 119.1(2) . . ?
F1 C6 C7 116.6(2) . . ?
C7 C6 C5 124.3(2) . . ?
O1 C7 C5 120.8(2) . 3_666 ?
O1 C7 C6 118.8(2) . . ?
C6 C7 C5 120.4(2) . 3_666 ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
