# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_F-radical
_audit_block_doi                 10.5517/cc147cg6
_database_code_depnum_ccdc_archive 'CCDC 1049767'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/cg501013x 2014
_audit_update_record             
;
2015-02-16 deposited with the CCDC.
2016-08-05 downloaded from the CCDC.
;
_audit_creation_method           MoPro12
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C7 F5 N2 S2'
_chemical_formula_sum            'C7 F5 N2 S2'
_chemical_formula_weight         271.204
_chemical_absolute_configuration -

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
N N 0.0061 0.0033 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
F F 0.0171 0.0103 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
S S 0.1246 0.1234 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z+1/2'
_cell_length_a                   17.9880(9)
_cell_length_b                   10.6195(5)
_cell_length_c                   10.8053(5)
_cell_angle_alpha                90.
_cell_angle_beta                 123.369(2)
_cell_angle_gamma                90.
_cell_volume                     1723.80(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    90
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.199
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.091
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1064
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_absorpt_correction_T_min  0.710
_exptl_absorpt_correction_T_max  0.753
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      90
_diffrn_detector                 'APEX-II CCD'
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'TXS rotating anode'
_diffrn_reflns_number            116368
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_sigmaI/netI    0.00704
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         48.88
_reflns_number_total             7900
_reflns_number_gt                7900
_reflns_threshold_expression     >3.0sigma(I)
_computing_cell_refinement       'SAINT V8.27B integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refinement of F¹ against reflections.
 The threshold expression of F² > 2sigma(F²) is
 used for calculating R-factors(gt) 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 F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    undef
# refall refxyz hetero heteroxyz constr 

_refine_ls_extinction_method     none
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         7900
_refine_ls_number_parameters     442
_refine_ls_number_restraints     0
# R-factors: R(F)  &  wR2(I) 
_refine_ls_R_factor_all          0.0100
## R_factor_all computed for  I/sigmaI >   3.00
_refine_ls_R_factor_gt           0.0100
_refine_ls_wR_factor_ref         0.0114
_refine_ls_wR_factor_gt          0.0114
_refine_ls_goodness_of_fit_ref   1.984
_refine_ls_restrained_S_all      0.000
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        48.88
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_diff_density_rms         ?
###  to get diff_density_max min & rms : 
###  run MoPro  : WRIT FOUR   to create FOURier file 
### run VMoPro : FOUR  FastFourierTransform  
### to get a 3D grid (Xplor format) on whole unit-cell
###  To get max min rms statistics
###  run VMoPro: GRID STAT   or 
###  open 3D xplor grid with MoProViewer 

loop_
_atom_site_type_symbol
_atom_site_label
_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_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.390281(7) 0.590004(9) 0.070847(11) 0.011565(2) Uani 1 d . . . .
S S2 0.407785(7) 0.586958(9) 0.279025(11) 0.011416(2) Uani 1 d . . . .
F F1 0.451209(19) 0.20793(3) 0.03393(3) 0.014292(15) Uani 1 d . . . .
F F2 0.43959(2) -0.04256(3) 0.04083(3) 0.016759(16) Uani 1 d . . . .
F F3 0.35368(3) -0.15092(3) 0.15525(5) 0.01999(2) Uani 1 d . . . .
F F4 0.28042(2) -0.00529(3) 0.26757(3) 0.015782(16) Uani 1 d . . . .
F F5 0.29057(2) 0.24485(3) 0.26411(4) 0.015913(17) Uani 1 d . . . .
N N1 0.378761(10) 0.437335(18) 0.04770(2) 0.011807(9) Uani 1 d . . . .
N N2 0.401060(10) 0.433981(18) 0.28379(2) 0.011457(9) Uani 1 d . . . .
C C1 0.385219(10) 0.376647(15) 0.161516(15) 0.009765(8) Uani 1 d . . . .
C C2 0.373063(10) 0.237928(14) 0.151821(14) 0.009625(7) Uani 1 d . . . .
C C3 0.407543(10) 0.160095(16) 0.090471(15) 0.010302(8) Uani 1 d . . . .
C C4 0.401733(11) 0.029756(15) 0.092343(17) 0.011760(9) Uani 1 d . . . .
C C5 0.358801(11) -0.026099(16) 0.152525(17) 0.012649(9) Uani 1 d . . . .
C C6 0.321791(11) 0.048396(15) 0.210533(16) 0.011525(9) Uani 1 d . . . .
C C7 0.328924(10) 0.178440(16) 0.209536(16) 0.010613(8) Uani 1 d . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.015802(15) 0.007714(13) 0.010530(11) 0.000990(10) 0.006831(10) 0.001517(9)
S2 0.016796(15) 0.007273(12) 0.013582(12) 0.000179(10) 0.010511(11)
-0.000858(9)
F1 0.01756(9) 0.01297(9) 0.01701(8) -0.00008(7) 0.01245(8) -0.00015(7)
F2 0.01892(10) 0.01258(9) 0.02024(9) 0.00285(8) 0.01170(9) -0.00300(8)
F3 0.02591(13) 0.00713(9) 0.02777(12) -0.00030(8) 0.01529(11) 0.00046(8)
F4 0.01685(9) 0.01400(9) 0.01764(8) -0.00399(7) 0.01021(8) 0.00130(7)
F5 0.01974(10) 0.01255(9) 0.02259(9) -0.00210(8) 0.01617(10) -0.00332(8)
N1 0.01658(6) 0.00844(5) 0.00964(4) -0.00021(3) 0.00672(4) 0.00021(4)
N2 0.01721(6) 0.00783(5) 0.01222(5) -0.00051(3) 0.00992(4) -0.00059(4)
C1 0.01222(5) 0.00731(5) 0.01005(4) -0.00005(3) 0.00630(4) -0.00009(3)
C2 0.01111(5) 0.00750(4) 0.01055(4) -0.00025(3) 0.00613(4) -0.00044(3)
C3 0.01178(5) 0.00863(5) 0.01096(4) 0.00019(4) 0.00654(4) -0.00059(3)
C4 0.01318(5) 0.00855(5) 0.01306(5) 0.00088(4) 0.00690(5) -0.00118(4)
C5 0.01450(5) 0.00734(5) 0.01492(5) -0.00020(4) 0.00734(5) -0.00008(3)
C6 0.01263(5) 0.00894(5) 0.01277(5) -0.00159(4) 0.00684(4) 0.00027(3)
C7 0.01209(5) 0.00860(5) 0.01230(4) -0.00099(4) 0.00743(4) -0.00077(3)

_geom_special_details            
;                                    
;

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 S2 2.09308(12) . ?
S1 N1 1.63615(10) . ?
S2 N2 1.63195(10) . ?
F1 C3 1.33266(12) . ?
F2 C4 1.33422(13) . ?
F3 C5 1.33014(14) . ?
F4 C6 1.32790(13) . ?
F5 C7 1.32987(13) . ?
N1 C1 1.33569(11) . ?
N2 C1 1.33543(11) . ?
C1 C2 1.48448(10) . ?
C2 C3 1.39985(9) . ?
C2 C7 1.40110(9) . ?
C3 C4 1.38906(10) . ?
C4 C5 1.38691(10) . ?
C5 C6 1.38598(10) . ?
C6 C7 1.38754(10) . ?

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S2 S1 N1 94.62(3) . . . ?
C3 C2 C7 116.85(6) . . . ?
C3 C2 C1 122.20(6) . . . ?
C7 C2 C1 120.90(6) . . . ?
C4 C3 C2 121.67(7) . . . ?
C5 C4 C3 119.92(7) . . . ?
C6 C5 C4 119.85(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
S1 S2 N2 C1 . . . . -2.118(10) ?
S1 N1 C1 N2 . . . . -1.101(12) ?
S1 N1 C1 C2 . . . . 178.079(7) ?
S2 S1 N1 C1 . . . . -0.437(10) ?
S2 N2 C1 N1 . . . . 2.443(12) ?
S2 N2 C1 C2 . . . . -176.744(7) ?
F1 C3 C4 F2 . . . . 0.756(19) ?
F1 C3 C4 C5 . . . . 178.651(14) ?
F1 C3 C2 C7 . . . . -179.456(14) ?
F1 C3 C2 C1 . . . . -1.819(14) ?
F2 C4 C5 F3 . . . . -1.65(2) ?
F2 C4 C5 C6 . . . . 177.953(11) ?
F2 C4 C3 C2 . . . . -176.130(14) ?
F3 C5 C6 F4 . . . . -0.66(2) ?
F3 C5 C6 C7 . . . . 178.838(9) ?
F3 C5 C4 C3 . . . . -179.57(3) ?
F4 C6 C5 C4 . . . . 179.73(2) ?
F4 C6 C7 F5 . . . . -1.780(19) ?
F4 C6 C7 C2 . . . . 179.223(8) ?
F5 C7 C6 C5 . . . . 178.729(14) ?
F5 C7 C2 C3 . . . . -177.000(15) ?
F5 C7 C2 C1 . . . . 5.331(14) ?
N1 S1 S2 N2 . . . . 1.384(10) ?
N1 C1 C2 C3 . . . . 39.932(14) ?
N1 C1 C2 C7 . . . . -142.53(2) ?
N2 C1 C2 C3 . . . . -140.84(2) ?
N2 C1 C2 C7 . . . . 36.704(14) ?
C1 C2 C3 C4 . . . . 174.937(8) ?
C1 C2 C7 C6 . . . . -175.715(8) ?
C2 C3 C4 C5 . . . . 1.766(12) ?
C2 C7 C6 C5 . . . . -0.268(12) ?
C3 C4 C5 C6 . . . . 0.034(12) ?
C3 C2 C7 C6 . . . . 1.955(12) ?
C4 C5 C6 C7 . . . . -0.768(12) ?
C4 C3 C2 C7 . . . . -2.700(12) ?


#---------------------------------------------#
#   ANHARMONIC PARAMETERS                     #
#---------------------------------------------#

loop_
_atom_site_anharm_GC_C_label
_atom_site_anharm_GC_C_111
_atom_site_anharm_GC_C_222
_atom_site_anharm_GC_C_333
_atom_site_anharm_GC_C_112
_atom_site_anharm_GC_C_122
_atom_site_anharm_GC_C_113
_atom_site_anharm_GC_C_133
_atom_site_anharm_GC_C_223
_atom_site_anharm_GC_C_233
_atom_site_anharm_GC_C_123
S1 2.95E-07 6.43E-06 2.37E-05 3.27E-05 4.73E-06 2.73E-05 2.08E-05 1.15E-05
2.09E-05 4.32E-05
S2 2.24E-07 -1.20E-05 -2.16E-05 1.29E-05 5.04E-05 -1.54E-05 -3.27E-05 4.94E-05
-3.88E-05 -1.94E-05

#---------------------------------------------#
#   MULTIPOLE PARAMETERS                      #
#---------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_radial_slater_n0
_atom_rho_multipole_radial_slater_zeta0
_atom_rho_multipole_radial_slater_n1
_atom_rho_multipole_radial_slater_zeta1
_atom_rho_multipole_radial_slater_n2
_atom_rho_multipole_radial_slater_zeta2
_atom_rho_multipole_radial_slater_n3
_atom_rho_multipole_radial_slater_zeta3
_atom_rho_multipole_radial_slater_n4
_atom_rho_multipole_radial_slater_zeta4
S1 5.82(2) 0. -0.046(7) 0.004(7) 0. 0.113(8) 0. -0. 0.091(6) 0.076(8) 0.
-0.134(8) -0.025(8) -0. 0. -0.206(9) -0.045(8) 0.023(13) 0. 0. -0.016(10)
0.008(13) -0. 0. -0.113(13) 0.002(10) 1.0524(17) 1.116(11) 4 3.612 4 3.612 4
3.612 6 3.612 8 3.612
S2 5.753(19) 0. -0.046(7) 0.011(7) -0. 0.116(8) 0. -0. 0.087(5) 0.087(7) -0.
-0.115(8) -0.045(8) 0. -0. -0.207(9) -0.053(8) 0.010(14) 0. -0. 0.026(9)
0.005(13) -0. 0. -0.136(13) -0.014(10) 1.0524(17) 1.116(11) 4 3.612 4 3.612 4
3.612 6 3.612 8 3.612
F1 7.241(14) 0. 0.007(6) -0.013(5) -0.012(5) -0.108(7) 0.007(6) -0.009(6)
0.011(6) 0.019(6) 0.009(4) 0.005(4) 0.003(4) -0.016(4) 0.009(4) -0.010(4)
-0.015(4) 0.011(5) -0.002(4) 0.004(4) -0.001(5) -0.003(5) -0.012(5) 0.006(5)
0.001(5) 0.000(5) 0.9899(9) 1.13(4) 2 5.186 2 5.186 2 5.186 3 5.186 4 5.186
F2 7.201(13) 0. 0.016(6) 0.015(6) -0.010(6) -0.097(7) -0.017(7) -0.018(6)
0.003(7) 0.009(7) 0.005(4) -0.009(4) -0.007(4) 0.001(4) 0.008(4) -0.002(4)
0.002(4) 0.015(6) -0.003(4) 0.001(4) -0.004(5) 0.009(5) 0.006(5) 0.006(5)
-0.008(5) -0.002(5) 0.9916(8) 1.13(4) 2 5.186 2 5.186 2 5.186 3 5.186 4 5.186
F3 7.139(13) 0. 0.019(7) 0.041(7) -0.023(6) -0.070(7) -0.004(7) -0.007(7)
0.008(9) 0.001(9) 0.008(4) 0.013(4) -0.027(4) -0.017(5) 0.018(4) 0.023(5)
-0.030(5) -0.017(6) 0.003(4) -0.001(4) 0.010(6) -0.006(6) -0.004(6) 0.007(6)
-0.013(6) -0.008(6) 0.9916(8) 1.13(4) 2 5.186 2 5.186 2 5.186 3 5.186 4 5.186
F4 7.201(13) 0. -0.004(6) -0.033(6) -0.035(6) -0.113(7) -0.012(6) -0.012(6)
0.011(7) -0.001(7) 0.015(4) 0.001(4) 0.002(4) 0.012(4) -0.018(4) -0.007(4)
0.012(4) 0.008(5) -0.002(4) 0.003(4) -0.001(5) 0.000(5) 0.012(5) 0.008(5)
-0.014(5) 0.001(5) 0.9916(8) 1.13(4) 2 5.186 2 5.186 2 5.186 3 5.186 4 5.186
F5 7.222(14) 0. 0.001(6) -0.009(6) -0.020(6) -0.116(8) 0.021(6) -0.008(6)
0.006(7) 0.009(7) -0.001(4) 0.003(4) -0.003(4) -0.023(4) -0.008(4) -0.005(4)
-0.009(4) 0.005(5) -0.001(4) 0.012(4) -0.007(5) -0.002(5) -0.008(5) 0.001(5)
0.009(5) 0.000(5) 0.9899(9) 1.13(4) 2 5.186 2 5.186 2 5.186 3 5.186 4 5.186
N1 5.09(2) 0. -0.095(6) -0.002(5) -0. -0.049(5) 0. 0. 0.022(5) 0.021(5) -0.
-0.024(5) 0.005(5) 0. -0. -0.070(5) -0.001(4) -0.002(6) -0. 0. -0.005(6)
0.000(6) 0. 0. -0.022(5) -0.005(5) 0.9933(15) 1.13(2) 2 3.811 2 3.811 2 3.811 3
3.811 4 3.811
N2 5.12(2) 0. -0.096(6) 0.016(5) 0. -0.053(5) 0. 0. 0.029(5) 0.033(5) -0.
-0.027(5) 0.020(5) -0. 0. -0.069(5) 0.006(4) -0.001(6) 0. -0. -0.001(6)
-0.017(6) 0. -0. -0.023(5) -0.026(5) 0.9933(15) 1.13(2) 2 3.811 2 3.811 2 3.811
3 3.811 4 3.811
C1 3.89(4) 0. 0.112(12) -0. -0. -0.207(12) -0. 0. -0.008(9) 0. -0. -0.010(9)
-0. 0. -0. -0.39(2) -0. 0.044(12) 0. 0. -0.039(11) -0. 0. 0. -0.016(12) -0.
1.008(4) 0.897(18) 2 3.130 2 3.130 2 3.130 3 3.130 4 3.130
C2 3.98(6) 0. 0.038(19) 0. -0. -0.212(16) 0. 0. 0.000(13) 0. 0. 0.021(13) 0.
-0. 0. -0.51(3) -0. 0.066(17) 0. -0. 0.006(15) -0. -0. -0. -0.03(2) 0. 1.008(4)
0.768(14) 2 3.130 2 3.130 2 3.130 3 3.130 4 3.130
C3 3.85(5) 0. 0.110(11) -0.027(9) 0. -0.131(8) 0. 0. -0.079(8) 0.002(8) -0.
0.067(7) -0.015(8) -0. -0. -0.302(16) 0.020(7) 0.035(9) 0. 0. -0.027(9)
-0.007(9) -0. 0. 0.036(10) 0.020(10) 1.011(3) 0.984(16) 2 3.130 2 3.130 2 3.130
3 3.130 4 3.130
C4 3.81(5) 0. 0.094(11) 0. -0. -0.099(8) 0. -0. -0.071(8) 0. -0. 0.076(7) -0.
-0. -0. -0.291(17) 0. 0.025(10) -0. 0. -0.037(10) 0. 0. 0. 0.051(10) 0.
1.012(3) 1.004(19) 2 3.130 2 3.130 2 3.130 3 3.130 4 3.130
C5 4.05(5) 0. 0.190(17) -0. -0. -0.233(12) -0. -0. -0.105(11) -0. 0. 0.079(10)
-0. -0. 0. -0.53(3) -0. 0.056(15) -0. 0. 0.013(14) -0. 0. 0. 0.043(16) -0.
1.009(4) 0.821(12) 2 3.130 2 3.130 2 3.130 3 3.130 4 3.130
C6 3.81(5) 0. 0.092(11) 0. -0. -0.097(8) 0. -0. -0.055(8) 0. -0. 0.075(7) -0.
0. -0. -0.281(17) -0. 0.041(10) 0. -0. -0.040(10) 0. -0. 0. 0.039(11) 0.
1.012(3) 1.004(19) 2 3.130 2 3.130 2 3.130 3 3.130 4 3.130
C7 3.82(5) 0. 0.107(11) -0.039(9) 0. -0.130(8) -0. 0. -0.095(8) -0.009(8) 0.
0.083(7) 0.005(8) 0. 0. -0.310(16) 0.032(8) 0.037(10) 0. -0. -0.013(10)
-0.009(9) -0. 0. 0.063(10) 0.020(10) 1.011(3) 0.984(16) 2 3.130 2 3.130 2 3.130
3 3.130 4 3.130

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
S1 S2 bX S1 N1 Y
S2 S1 bX S2 N2 Y
F1 C3 Z F1 C4 X
F2 C4 Z F2 C5 X
F3 C5 Z F3 C6 X
F4 C6 Z F4 C5 X
F5 C7 Z F5 C6 X
N1 S1 bX N1 C1 Y
N2 S2 bX N2 C1 Y
C1 N2 bX C1 N1 Y
C2 C3 bX C2 C7 Y
C3 C4 bX C3 C2 Y
C4 C5 bX C4 C3 Y
C5 C6 bX C5 C4 Y
C6 C5 bX C6 C7 Y
C7 C6 bX C7 C2 Y
####################################################################### 
# 
# 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_NF4-radical
_database_code_depnum_ccdc_archive 'CCDC 1479036'
_audit_update_record             
;
2016-05-10 deposited with the CCDC.
2016-08-05 downloaded from the CCDC.
;
_audit_creation_method           MoPro12
_chemical_name_systematic        4-perfluoropyridyl-1,2,3,5-dithiadiazolyl
_chemical_name_common            ?
_chemical_formula_moiety         'C6 F4 N3 S2'
_chemical_formula_sum            'C6 F4 N3 S2'
_chemical_formula_weight         254.202
_chemical_absolute_configuration -

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
N N 0.0061 0.0033 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
F F 0.0171 0.0103 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
S S 0.1246 0.1234 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z+1/2'
_cell_length_a                   17.7810(19)
_cell_length_b                   9.6259(10)
_cell_length_c                   11.3461(12)
_cell_angle_alpha                90.
_cell_angle_beta                 125.714(2)
_cell_angle_gamma                90.
_cell_volume                     1576.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    90
_cell_measurement_reflns_used    368
_cell_measurement_theta_min      1.75
_cell_measurement_theta_max      33.5
_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.162
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.103
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.142
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_absorpt_correction_T_min  0.863
_exptl_absorpt_correction_T_max  0.898
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      90
_diffrn_detector                 'APEX-II CCD'
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'TXS rotating anode'
_diffrn_reflns_number            90319
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_sigmaI/netI    0.02968
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         53.91
_reflns_number_total             9721
_reflns_number_gt                8260
_reflns_threshold_expression     >2.0sigma(I)
_computing_cell_refinement       'SAINT V8.27B integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'OLEX 2, SHELX 2014'
_computing_structure_refinement  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refinement of F¹ against reflections.
 The threshold expression of F² > 2sigma(F²) is
 used for calculating R-factors(gt) 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 F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    undef
# refall refxyz hetero heteroxyz constr 

_refine_ls_extinction_method     none
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         9721
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
# R-factors: R(F)  &  wR2(I) 
_refine_ls_R_factor_all          0.0195
_refine_ls_R_factor_gt           0.0133
_refine_ls_wR_factor_ref         0.0177
_refine_ls_wR_factor_gt          0.0174
_refine_ls_goodness_of_fit_ref   0.926
# GOF computed assuming  all parameters refined:     384
_refine_ls_restrained_S_all      0.000
_refine_ls_shift/su_mean         -0.002

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        53.91
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_diff_density_rms         ?
###  to get diff_density_max min & rms : 
###  run MoPro  : WRIT FOUR   to create FOURier file 
### run VMoPro : FOUR  FastFourierTransform  
### to get a 3D grid (Xplor format) on whole unit-cell
###  To get max min rms statistics
###  run VMoPro: GRID STAT   or 
###  open 3D xplor grid with MoProViewer 

loop_
_atom_site_type_symbol
_atom_site_label
_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_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.600337(9) 0.613680(12) 0.738044(15) 0.012218(3) Uani 1 d . . . .
S S2 0.613156(9) 0.617053(12) 0.933524(13) 0.012051(3) Uani 1 d . . . .
F F1 0.702031(17) 0.21735(2) 0.74003(3) 0.013947(13) Uani 1 d . . . .
F F2 0.699871(17) -0.05899(2) 0.74182(3) 0.013669(13) Uani 1 d . . . .
F F3 0.560814(18) -0.07164(2) 0.96952(3) 0.014216(13) Uani 1 d . . . .
F F4 0.551662(17) 0.20444(2) 0.97449(3) 0.012675(12) Uani 1 d . . . .
N N1 0.606089(12) 0.44471(2) 0.73337(2) 0.011836(10) Uani 1 d . . . .
N N2 0.622640(12) 0.448753(19) 0.95469(2) 0.011795(9) Uani 1 d . . . .
N N3 0.630962(11) -0.06467(2) 0.856640(17) 0.010531(11) Uani 1 d . . . .
C C1 0.617869(12) 0.381642(17) 0.847586(18) 0.009178(9) Uani 1 d . . . .
C C2 0.625726(11) 0.227989(17) 0.855764(17) 0.008421(9) Uani 1 d . . . .
C C3 0.664336(12) 0.153920(17) 0.797178(18) 0.009409(9) Uani 1 d . . . .
C C4 0.664486(12) 0.009533(17) 0.799922(19) 0.009780(9) Uani 1 d . . . .
C C5 0.596346(12) 0.003712(17) 0.915046(19) 0.009862(9) Uani 1 d . . . .
C C6 0.592105(12) 0.147526(16) 0.918396(18) 0.009076(9) Uani 1 d . . . .


_geom_special_details            
;                                    
;

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 S2 2.0933(3) . ?
S1 N1 1.63254(18) . ?
S2 N2 1.63199(19) . ?
F1 C3 1.32280(14) . ?
F2 C4 1.32279(14) . ?
F3 C5 1.32780(14) . ?
F4 C6 1.32540(13) . ?
N1 C1 1.33228(19) . ?
N2 C1 1.33454(18) . ?
N3 C5 1.31432(14) . ?
N3 C4 1.31432(14) . ?
C1 C2 1.48344(17) . ?
C2 C3 1.39797(13) . ?
C2 C6 1.39937(14) . ?
C3 C4 1.39017(17) . ?
C5 C6 1.38812(17) . ?

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S2 S1 N1 94.57(4) . . . ?
C5 N3 C4 117.03(7) . . . ?
C3 C2 C6 115.67(6) . . . ?
C3 C2 C1 122.22(7) . . . ?
C6 C2 C1 122.08(7) . . . ?
C4 C3 C2 119.62(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
S1 S2 N2 C1 . . . . -0.630(10) ?
S1 N1 C1 N2 . . . . 1.350(13) ?
S1 N1 C1 C2 . . . . -178.918(8) ?
S2 S1 N1 C1 . . . . -1.403(10) ?
S2 N2 C1 N1 . . . . -0.285(13) ?
S2 N2 C1 C2 . . . . 179.972(8) ?
F1 C3 C4 F2 . . . . -1.865(15) ?
F1 C3 C4 N3 . . . . 178.453(16) ?
F1 C3 C2 C6 . . . . -177.210(14) ?
F1 C3 C2 C1 . . . . 4.846(12) ?
F2 C4 N3 C5 . . . . 179.612(12) ?
F2 C4 C3 C2 . . . . 178.864(6) ?
F3 C5 N3 C4 . . . . 178.642(16) ?
F3 C5 C6 F4 . . . . -0.775(15) ?
F3 C5 C6 C2 . . . . -177.279(11) ?
F4 C6 C5 N3 . . . . 176.913(16) ?
F4 C6 C2 C3 . . . . -178.235(13) ?
F4 C6 C2 C1 . . . . -0.288(12) ?
N1 S1 S2 N2 . . . . 1.101(12) ?
N1 C1 C2 C3 . . . . 31.091(16) ?
N1 C1 C2 C6 . . . . -146.72(3) ?
N2 C1 C2 C3 . . . . -149.16(3) ?
N2 C1 C2 C6 . . . . 33.026(16) ?
N3 C5 C6 C2 . . . . 0.410(12) ?
N3 C4 C3 C2 . . . . -0.818(13) ?
C1 C2 C3 C4 . . . . -175.908(10) ?
C1 C2 C6 C5 . . . . 176.099(10) ?
C3 C4 N3 C5 . . . . -0.702(13) ?
C3 C2 C6 C5 . . . . -1.848(12) ?
C4 N3 C5 C6 . . . . 0.909(13) ?
C4 C3 C2 C6 . . . . 2.036(12) ?
_chemical_properties_physical    Air-sensitive
