# 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_ic16335
_database_code_depnum_ccdc_archive 'CCDC 1026818'
_audit_update_record             
;
2014-09-29 deposited with the CCDC.
2015-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ' 5,6-difluorobenzo-2,1,3-thiadiazole'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H6 F2 N2 S3'
_chemical_formula_weight         336.39

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   15.7727(9)
_cell_length_b                   4.8184(3)
_cell_length_c                   17.7825(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.765(5)
_cell_angle_gamma                90.00
_cell_volume                     1306.83(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1191
_cell_measurement_theta_min      5.1390
_cell_measurement_theta_max      70.3050

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    5.361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73034
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Gemini A'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4717
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0582
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         5.14
_diffrn_reflns_theta_max         67.97
_reflns_number_total             2375
_reflns_number_gt                1680
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_cell_refinement       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_data_reduction        
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2375
_refine_ls_number_parameters     228
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0641
_refine_ls_wR_factor_ref         0.1914
_refine_ls_wR_factor_gt          0.1775
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.18129(14) 0.5101(5) 0.32442(9) 0.0519(6) Uani 0.850(7) 1 d PU A 1
C3 C 0.0652(10) 0.527(4) 0.3993(10) 0.054(3) Uani 0.850(7) 1 d PU A 1
H3 H 0.0321 0.4922 0.4361 0.065 Uiso 0.850(7) 1 calc PR A 1
S2 S 0.4255(5) -0.599(2) 0.6158(5) 0.0502(19) Uani 0.305(7) 1 d PU A 1
C12 C 0.3083(16) -0.583(5) 0.6849(13) 0.049(3) Uani 0.305(7) 1 d PU A 1
H12 H 0.2564 -0.5346 0.6995 0.058 Uiso 0.305(7) 1 calc PR A 1
S1' S 0.0460(14) 0.513(7) 0.4103(15) 0.055(4) Uani 0.150(7) 1 d PU A 2
C3' C 0.167(4) 0.498(13) 0.343(3) 0.054(4) Uani 0.150(7) 1 d PU A 2
H3' H 0.2197 0.4500 0.3296 0.065 Uiso 0.150(7) 1 calc PR A 2
S2' S 0.28466(16) -0.5644(6) 0.70086(13) 0.0508(7) Uani 0.695(7) 1 d PU A 2
C12' C 0.4020(10) -0.606(4) 0.6261(10) 0.051(3) Uani 0.695(7) 1 d PU A 2
H12' H 0.4354 -0.5801 0.5891 0.062 Uiso 0.695(7) 1 calc PR A 2
S3 S 0.39715(9) -0.0719(4) 0.41306(8) 0.0679(5) Uani 1 1 d . . .
F1 F 0.08636(19) 0.1741(8) 0.53201(18) 0.0694(9) Uani 1 1 d . A .
F2 F 0.16416(19) -0.1898(8) 0.62629(17) 0.0639(9) Uani 1 1 d . . .
N1 N 0.3115(3) 0.1204(10) 0.3964(2) 0.0516(10) Uani 1 1 d . A .
N2 N 0.3888(2) -0.2421(10) 0.4889(2) 0.0502(10) Uani 1 1 d . . .
C1 C 0.0966(4) 0.7269(12) 0.2957(3) 0.0618(14) Uani 1 1 d . . .
H1 H 0.0902 0.8456 0.2519 0.074 Uiso 1 1 calc R A 1
C2 C 0.0383(3) 0.7212(12) 0.3387(3) 0.0571(12) Uani 1 1 d . A .
H2 H -0.0132 0.8313 0.3297 0.068 Uiso 1 1 calc R B 1
C4 C 0.1427(3) 0.3905(10) 0.4016(2) 0.0429(10) Uani 1 1 d . . .
C5 C 0.1890(3) 0.1810(10) 0.4560(2) 0.0405(9) Uani 1 1 d . A .
C6 C 0.2702(3) 0.0582(10) 0.4508(2) 0.0393(9) Uani 1 1 d . . .
C7 C 0.3151(3) -0.1531(10) 0.5046(2) 0.0393(9) Uani 1 1 d . A .
C8 C 0.2812(3) -0.2483(10) 0.5683(2) 0.0387(9) Uani 1 1 d . . .
C9 C 0.2048(3) -0.1247(10) 0.5708(2) 0.0441(10) Uani 1 1 d . A .
C10 C 0.1607(3) 0.0821(10) 0.5174(2) 0.0443(10) Uani 1 1 d . . .
C11 C 0.3259(3) -0.4613(10) 0.6234(2) 0.0423(10) Uani 1 1 d . A .
C13 C 0.3670(3) -0.7897(11) 0.7303(3) 0.0536(12) Uani 1 1 d . . .
H13 H 0.3637 -0.8884 0.7757 0.064 Uiso 1 1 calc R A 1
C14 C 0.4269(3) -0.7994(11) 0.6890(3) 0.0529(11) Uani 1 1 d . A .
H14 H 0.4729 -0.9315 0.7036 0.063 Uiso 1 1 calc R C 1

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0650(11) 0.0516(9) 0.0374(9) 0.0082(7) 0.0096(6) 0.0059(7)
C3 0.062(6) 0.055(4) 0.046(5) 0.003(4) 0.013(4) 0.007(5)
S2 0.064(4) 0.049(3) 0.036(3) 0.006(2) 0.011(3) 0.013(3)
C12 0.066(6) 0.050(5) 0.032(6) -0.005(5) 0.016(5) 0.006(6)
S1' 0.056(7) 0.056(5) 0.052(7) 0.008(5) 0.011(5) 0.012(6)
C3' 0.060(7) 0.055(6) 0.046(7) 0.005(6) 0.011(6) 0.009(6)
S2' 0.0677(14) 0.0520(12) 0.0355(10) 0.0067(8) 0.0181(7) 0.0069(10)
C12' 0.068(6) 0.055(4) 0.032(4) 0.000(3) 0.015(4) 0.001(5)
S3 0.0641(8) 0.0933(12) 0.0550(7) 0.0241(7) 0.0313(6) 0.0229(7)
F1 0.0664(17) 0.086(2) 0.0650(17) 0.0190(17) 0.0342(14) 0.0319(18)
F2 0.0695(16) 0.077(2) 0.0549(15) 0.0213(15) 0.0333(13) 0.0198(16)
N1 0.056(2) 0.060(3) 0.0391(18) 0.0084(18) 0.0132(16) 0.008(2)
N2 0.050(2) 0.063(3) 0.0404(18) 0.0092(17) 0.0156(15) 0.0160(19)
C1 0.086(3) 0.048(3) 0.041(2) -0.003(2) -0.004(2) 0.001(3)
C2 0.061(3) 0.053(3) 0.049(2) -0.003(2) -0.003(2) 0.008(2)
C4 0.049(2) 0.041(2) 0.0335(18) -0.0041(17) 0.0025(16) 0.001(2)
C5 0.047(2) 0.038(2) 0.0329(18) -0.0071(17) 0.0040(16) -0.0004(18)
C6 0.049(2) 0.041(2) 0.0267(17) -0.0034(16) 0.0073(15) -0.0030(19)
C7 0.046(2) 0.041(2) 0.0305(18) -0.0017(17) 0.0085(15) 0.0005(18)
C8 0.047(2) 0.040(2) 0.0283(17) -0.0034(16) 0.0073(15) -0.0023(18)
C9 0.052(2) 0.047(3) 0.0361(19) -0.0024(18) 0.0159(17) -0.005(2)
C10 0.046(2) 0.049(3) 0.040(2) -0.0048(19) 0.0135(17) 0.002(2)
C11 0.054(2) 0.042(2) 0.0297(18) -0.0038(17) 0.0079(16) -0.002(2)
C13 0.073(3) 0.048(3) 0.037(2) 0.001(2) 0.008(2) -0.001(2)
C14 0.066(3) 0.044(3) 0.046(2) -0.001(2) 0.010(2) 0.004(2)

_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 1.670(6) . ?
S1 C4 1.735(5) . ?
C3 C4 1.380(17) . ?
C3 C2 1.408(19) . ?
S2 C14 1.619(11) . ?
S2 C11 1.742(9) . ?
C12 C11 1.33(3) . ?
C12 C13 1.45(3) . ?
S1' C2 1.60(3) . ?
S1' C4 1.68(2) . ?
C3' C4 1.31(6) . ?
C3' C1 1.64(6) . ?
S2' C13 1.671(6) . ?
S2' C11 1.739(5) . ?
C12' C11 1.380(18) . ?
C12' C14 1.431(19) . ?
S3 N1 1.602(4) . ?
S3 N2 1.612(4) . ?
F1 C10 1.339(5) . ?
F2 C9 1.344(5) . ?
N1 C6 1.331(6) . ?
N2 C7 1.334(6) . ?
C1 C2 1.337(8) . ?
C4 C5 1.458(6) . ?
C5 C10 1.368(7) . ?
C5 C6 1.435(6) . ?
C6 C7 1.452(6) . ?
C7 C8 1.444(6) . ?
C8 C9 1.355(6) . ?
C8 C11 1.469(6) . ?
C9 C10 1.428(7) . ?
C13 C14 1.336(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C4 92.0(3) . . ?
C4 C3 C2 115.5(10) . . ?
C14 S2 C11 89.5(5) . . ?
C11 C12 C13 121.4(17) . . ?
C2 S1' C4 91.9(11) . . ?
C4 C3' C1 112(4) . . ?
C13 S2' C11 90.9(3) . . ?
C11 C12' C14 114.8(10) . . ?
N1 S3 N2 101.8(2) . . ?
C6 N1 S3 106.3(3) . . ?
C7 N2 S3 105.9(3) . . ?
C2 C1 C3' 100(2) . . ?
C2 C1 S1 115.1(4) . . ?
C3' C1 S1 15.6(19) . . ?
C1 C2 C3 109.6(7) . . ?
C1 C2 S1' 123.0(9) . . ?
C3 C2 S1' 13.7(12) . . ?
C3' C4 C3 103(3) . . ?
C3' C4 C5 127(3) . . ?
C3 C4 C5 129.8(8) . . ?
C3' C4 S1' 113(3) . . ?
C3 C4 S1' 10.3(15) . . ?
C5 C4 S1' 119.7(9) . . ?
C3' C4 S1 5(3) . . ?
C3 C4 S1 107.7(7) . . ?
C5 C4 S1 122.5(3) . . ?
S1' C4 S1 117.7(9) . . ?
C10 C5 C6 112.7(4) . . ?
C10 C5 C4 124.1(4) . . ?
C6 C5 C4 123.2(4) . . ?
N1 C6 C5 124.4(4) . . ?
N1 C6 C7 113.0(4) . . ?
C5 C6 C7 122.7(4) . . ?
N2 C7 C8 125.4(4) . . ?
N2 C7 C6 113.0(4) . . ?
C8 C7 C6 121.6(4) . . ?
C9 C8 C7 113.3(4) . . ?
C9 C8 C11 124.4(4) . . ?
C7 C8 C11 122.3(4) . . ?
F2 C9 C8 121.1(4) . . ?
F2 C9 C10 114.1(4) . . ?
C8 C9 C10 124.8(4) . . ?
F1 C10 C5 121.3(4) . . ?
F1 C10 C9 113.9(4) . . ?
C5 C10 C9 124.8(4) . . ?
C12 C11 C12' 96.2(12) . . ?
C12 C11 C8 133.7(11) . . ?
C12' C11 C8 130.0(8) . . ?
C12 C11 S2' 12.9(11) . . ?
C12' C11 S2' 109.0(7) . . ?
C8 C11 S2' 121.0(3) . . ?
C12 C11 S2 106.1(11) . . ?
C12' C11 S2 10.2(9) . . ?
C8 C11 S2 120.2(4) . . ?
S2' C11 S2 118.7(4) . . ?
C14 C13 C12 99.1(10) . . ?
C14 C13 S2' 116.9(4) . . ?
C12 C13 S2' 17.9(9) . . ?
C13 C14 C12' 108.4(7) . . ?
C13 C14 S2 123.7(5) . . ?
C12' C14 S2 15.7(7) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        67.97
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.723
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.087
