#------------------------------------------------------------------------------
#$Date: 2017-03-05 08:38:24 +0100 (dom 05 de mar de 2017) $
#$Revision: 193954 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/54/1545492.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1545492
loop_
_publ_author_name
'Partl, Gabriel'
'Laus, Gerhard'
'Wurst, Klaus'
'Kopacka, Holger'
'Müller, Thomas'
'Huppertz, Hubert'
'Schottenberger, Herwig'
_publ_section_title
;
 2,5-Bis[(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)sulfanyl]-1,3,4-thiadiazole
;
_journal_coeditor_code           HB4113
_journal_issue                   2
_journal_name_full               IUCrData
_journal_page_first              x170110
_journal_paper_doi               10.1107/S2414314617001109
_journal_volume                  2
_journal_year                    2017
_chemical_formula_iupac          'C18 H8 F26 N2 S3'
_chemical_formula_moiety         'C18 H8 F26 N2 S3'
_chemical_formula_sum            'C18 H8 F26 N2 S3'
_chemical_formula_weight         842.44
_chemical_name_systematic
2,5-Bis[(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)sulfanyl]-1,3,4-thiadiazole
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 94.442(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   41.014(11)
_cell_length_b                   5.7338(15)
_cell_length_c                   11.880(3)
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    176(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      3.0
_cell_volume                     2785.4(13)
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
Mercury (Macrae et al., 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
XT in SHELXTL (Sheldrick, 2008)
;
_diffrn_ambient_temperature      176(2)
_diffrn_detector_area_resol_mean 10.4
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multi layered optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            26073
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.989
_exptl_absorpt_coefficient_mu    0.458
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_correction_T_min  0.844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.009
_exptl_crystal_description       prism
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.248
_refine_ls_extinction_coef       0.0025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         2448
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0443P)²+5.7325P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.0990
_reflns_number_gt                2213
_reflns_number_total             2448
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4113sup1.cif
_cod_data_source_block           I
_cod_database_code               1545492
_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.
;
_shelx_estimated_absorpt_t_min   0.930
_shelx_estimated_absorpt_t_max   0.977
loop_
_space_group_symop_operation_xyz
'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, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.5000 1.00393(13) 0.7500 0.0257(2) Uani d 1 . .
S S2 0.53603(2) 0.85182(11) 0.55112(5) 0.0335(2) Uani d 1 . .
N N1 0.50855(5) 0.5709(3) 0.70144(15) 0.0275(4) Uani d 1 . .
C C1 0.51458(5) 0.7812(4) 0.66790(17) 0.0230(5) Uani d 1 . .
C C2 0.55301(5) 0.5683(4) 0.52066(19) 0.0283(5) Uani d 1 . .
H H2A 0.5636 0.4978 0.5903 0.034 Uiso calc 1 . .
H H2B 0.5356 0.4619 0.4894 0.034 Uiso calc 1 . .
C C3 0.57815(6) 0.6099(4) 0.4343(2) 0.0321(5) Uani d 1 . .
H H3A 0.5670 0.6765 0.3646 0.039 Uiso calc 1 . .
H H3B 0.5945 0.7248 0.4650 0.039 Uiso calc 1 . .
C C4 0.59534(5) 0.3881(4) 0.40543(18) 0.0253(5) Uani d 1 . .
C C5 0.62393(5) 0.4299(4) 0.33031(19) 0.0269(5) Uani d 1 . .
C C6 0.63965(5) 0.2116(4) 0.28023(19) 0.0285(5) Uani d 1 . .
C C7 0.67203(6) 0.2533(4) 0.2252(2) 0.0324(5) Uani d 1 . .
C C8 0.68717(6) 0.0386(5) 0.1714(2) 0.0426(7) Uani d 1 . .
C C9 0.71765(7) 0.0801(7) 0.1079(3) 0.0549(8) Uani d 1 . .
F F1 0.60748(4) 0.2780(3) 0.50030(12) 0.0435(4) Uani d 1 . .
F F2 0.57418(3) 0.2354(3) 0.35119(14) 0.0485(4) Uani d 1 . .
F F3 0.64731(3) 0.5471(3) 0.39435(14) 0.0452(4) Uani d 1 . .
F F4 0.61347(4) 0.5721(3) 0.24509(13) 0.0509(5) Uani d 1 . .
F F5 0.64402(4) 0.0478(3) 0.35936(13) 0.0468(4) Uani d 1 . .
F F6 0.61772(3) 0.1280(3) 0.19835(14) 0.0530(5) Uani d 1 . .
F F7 0.69446(4) 0.3290(3) 0.30676(16) 0.0614(5) Uani d 1 . .
F F8 0.66726(4) 0.4198(3) 0.14744(16) 0.0605(5) Uani d 1 . .
F F9 0.6973(3) -0.1100(18) 0.2579(8) 0.065(3) Uani d 0.55 A 1
F F10 0.6653(2) -0.0771(12) 0.1052(10) 0.0508(16) Uani d 0.55 A 1
F F11 0.7399(4) 0.197(3) 0.1638(13) 0.100(5) Uani d 0.55 B 1
F F12 0.70735(19) 0.1862(16) 0.0105(6) 0.0701(19) Uani d 0.55 B 1
F F13 0.7295(3) -0.140(2) 0.0725(10) 0.064(2) Uani d 0.55 B 1
F F9A 0.6907(3) -0.1311(19) 0.2408(11) 0.073(4) Uani d 0.45 A 2
F F10A 0.6647(4) -0.011(2) 0.0816(14) 0.118(6) Uani d 0.45 A 2
F F11A 0.7417(5) 0.128(4) 0.1932(19) 0.103(7) Uani d 0.45 B 2
F F12A 0.7178(3) 0.267(2) 0.0470(10) 0.123(5) Uani d 0.45 B 2
F F13A 0.7288(4) -0.072(3) 0.0679(16) 0.099(5) Uani d 0.45 B 2
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'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C1 S1 C1 2_656 . 85.62(15)
C1 S2 C2 . . 100.09(10)
C1 N1 N1 . 2_656 111.92(12)
N1 C1 S1 . . 115.27(16)
N1 C1 S2 . . 125.32(16)
S1 C1 S2 . . 119.41(13)
C3 C2 S2 . . 106.43(16)
C3 C2 H2A . . 110.4
S2 C2 H2A . . 110.4
C3 C2 H2B . . 110.4
S2 C2 H2B . . 110.4
H2A C2 H2B . . 108.6
C4 C3 C2 . . 111.9(2)
C4 C3 H3A . . 109.2
C2 C3 H3A . . 109.2
C4 C3 H3B . . 109.2
C2 C3 H3B . . 109.2
H3A C3 H3B . . 107.9
F1 C4 F2 . . 105.92(19)
F1 C4 C3 . . 110.69(18)
F2 C4 C3 . . 111.02(18)
F1 C4 C5 . . 107.84(17)
F2 C4 C5 . . 108.12(18)
C3 C4 C5 . . 112.95(19)
F4 C5 F3 . . 107.01(19)
F4 C5 C4 . . 108.44(17)
F3 C5 C4 . . 106.73(17)
F4 C5 C6 . . 108.62(18)
F3 C5 C6 . . 108.63(17)
C4 C5 C6 . . 116.98(19)
F5 C6 F6 . . 107.6(2)
F5 C6 C7 . . 109.59(19)
F6 C6 C7 . . 107.13(19)
F5 C6 C5 . . 109.65(18)
F6 C6 C5 . . 106.74(18)
C7 C6 C5 . . 115.8(2)
F8 C7 F7 . . 108.8(2)
F8 C7 C8 . . 109.1(2)
F7 C7 C8 . . 106.24(19)
F8 C7 C6 . . 108.65(19)
F7 C7 C6 . . 107.77(19)
C8 C7 C6 . . 116.1(2)
F10 C8 F9 . . 106.6(7)
F9A C8 F10A . . 112.2(9)
F9A C8 C9 . . 112.5(7)
F10 C8 C9 . . 109.2(5)
F9 C8 C9 . . 104.7(6)
F10A C8 C9 . . 99.9(7)
F9A C8 C7 . . 111.7(6)
F10 C8 C7 . . 111.7(4)
F9 C8 C7 . . 107.1(5)
F10A C8 C7 . . 102.6(6)
C9 C8 C7 . . 116.9(3)
F13A C9 F12A . . 113.0(12)
F11 C9 F12 . . 112.0(10)
F13A C9 F11A . . 100.2(12)
F12A C9 F11A . . 102.2(11)
F11 C9 F13 . . 111.9(8)
F12 C9 F13 . . 103.7(6)
F13A C9 C8 . . 118.0(10)
F11 C9 C8 . . 113.8(7)
F12A C9 C8 . . 116.4(5)
F12 C9 C8 . . 106.3(4)
F11A C9 C8 . . 103.5(10)
F13 C9 C8 . . 108.5(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 C1 2_656 1.741(2)
S1 C1 . 1.741(2)
S2 C1 . 1.747(2)
S2 C2 . 1.816(2)
N1 C1 . 1.300(3)
N1 N1 2_656 1.396(4)
C2 C3 . 1.529(3)
C2 H2A . 0.9900
C2 H2B . 0.9900
C3 C4 . 1.506(3)
C3 H3A . 0.9900
C3 H3B . 0.9900
C4 F1 . 1.353(3)
C4 F2 . 1.360(3)
C4 C5 . 1.546(3)
C5 F4 . 1.344(3)
C5 F3 . 1.355(3)
C5 C6 . 1.548(3)
C6 F5 . 1.331(3)
C6 F6 . 1.360(3)
C6 C7 . 1.544(3)
C7 F8 . 1.332(3)
C7 F7 . 1.355(3)
C7 C8 . 1.540(4)
C8 F9A . 1.277(12)
C8 F10 . 1.325(11)
C8 F9 . 1.374(9)
C8 F10A . 1.383(16)
C8 C9 . 1.528(4)
C9 F13A . 1.108(15)
C9 F11 . 1.275(15)
C9 F12A . 1.293(12)
C9 F12 . 1.347(10)
C9 F11A . 1.38(2)
C9 F13 . 1.429(11)

_cod_database_fobs_code 1545492
