#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/17/2001744.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_2001744
loop_
_publ_author_name
'Pohl, E.'
'Herbst-Irmer, R.'
'Sheldrick, G. M.'
_publ_section_title
;Structure of
 4,6-bis(trifluoromethyl)-2,2-bis[2,4,6-tris(trifluoromethyl)phenylthio]-1-thiabenzocyclobutene
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1026
_journal_page_last               1028
_journal_paper_doi               10.1107/S0108270192012526
_journal_volume                  49
_journal_year                    1993
_chemical_formula_sum            'C27 H6 F24 S3'
_chemical_formula_weight         882.50
_chemical_name_systematic
;
 8,8-Bis(2,4,6-tris(trifluoromethyl)thiophenolat)
 -3,5-trifluoromethyl-7-thia-benzocyclobutene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 93.19(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.721(4)
_cell_length_b                   10.062(2)
_cell_length_c                   17.284(3)
_cell_measurement_reflns_used    48
_cell_measurement_temperature    153.0(10)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      10
_cell_volume                     3077.1(11)
_computing_cell_refinement       'Stoe DIF4'
_computing_data_collection       'Stoe DIF4'
_computing_data_reduction        'Stoe REDU4'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material  SHELXL-92
_computing_structure_refinement  'SHELXL-92 (Sheldrick, 1992)'
_computing_structure_solution    'SHELXS-92 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153.0(10)
_diffrn_measurement_device       'Stoe-Siemens AED four-circle diffractometer'
_diffrn_measurement_method       'Profile data from 2θ/ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6164
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         4.00
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  90
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.409
_exptl_absorpt_correction_T_max  0.786
_exptl_absorpt_correction_T_min  0.738
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.905
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         .663
_refine_diff_density_min         -.409
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.067
_refine_ls_goodness_of_fit_obs   1.061
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         5355
_refine_ls_number_restraints     465
_refine_ls_restrained_S_all      1.297
_refine_ls_restrained_S_obs      1.288
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_obs          0.0465
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fₒ²)+(0.0424P)²+5.6388P] where P=(Fₒ²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1254
_refine_ls_wR_factor_obs         0.1061
_reflns_number_observed          4392
_reflns_number_total             5372
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            sh1032.cif
_cod_data_source_block           gad
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(F~o~^2^)+(0.0424P)^2^+5.6388P] where P=(F~o~^2^+2F~c~^2^)/3'
was changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(F~o~^2^)+(0.0424P)^2^+5.6388P] where
P=(F~o~^2^+2F~c~^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               2001744
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'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.2510(2) 0.5766(4) 0.5447(2) 0.028(2) Uani d . 1 . C
S1 0.35736(5) 0.56424(9) 0.53927(6) 0.0316(4) Uani d . 1 . S
C11 0.3202(2) 0.4250(3) 0.4888(2) 0.026(2) Uani d . 1 . C
C12 0.3452(2) 0.3169(4) 0.4485(2) 0.030(2) Uani d . 1 . C
C121 0.4269(2) 0.2991(4) 0.4360(3) 0.043(2) Uani d . 1 . C
F121 0.4668(2) 0.2761(5) 0.5010(2) 0.1057(15) Uani d . 1 . F
F122 0.4403(2) 0.1992(3) 0.3891(2) 0.087(2) Uani d . 1 . F
F123 0.4570(2) 0.4054(3) 0.4064(2) 0.081(2) Uani d . 1 . F
C13 0.2896(2) 0.2278(4) 0.4212(2) 0.032(2) Uani d . 1 . C
H13 0.3035(2) 0.1534(4) 0.3946(2) 0.038 Uiso calc R 1 . H
C14 0.2137(2) 0.2488(4) 0.4331(2) 0.029(2) Uani d D 1 . C
C141 0.1555(2) 0.1510(4) 0.4035(2) 0.037(2) Uani d D 1 . C
F141 0.1092(3) 0.1185(7) 0.4557(2) 0.116(4) Uani d PD 0.837(4) 1 F
F142 0.1849(2) 0.0418(3) 0.3764(4) 0.085(2) Uani d PD 0.837(4) 1 F
F143 0.1135(2) 0.1987(3) 0.3446(3) 0.071(2) Uani d PD 0.837(4) 1 F
F144 0.1626(13) 0.114(3) 0.3320(7) 0.116(4) Uani d PD 0.163(4) 2 F
F145 0.0857(4) 0.1928(15) 0.4068(17) 0.085(2) Uani d PD 0.163(4) 2 F
F146 0.1573(12) 0.0392(13) 0.4439(12) 0.071(2) Uani d PD 0.163(4) 2 F
C15 0.1890(2) 0.3613(4) 0.4728(2) 0.026(2) Uani d . 1 . C
H15 0.1387(2) 0.3763(4) 0.4802(2) 0.031 Uiso calc R 1 . H
C16 0.2445(2) 0.4475(3) 0.4999(2) 0.025(2) Uani d . 1 . C
S2 0.21823(5) 0.57716(10) 0.64345(5) 0.0330(5) Uani d . 1 . S
C21 0.1685(2) 0.4234(4) 0.6509(2) 0.028(2) Uani d . 1 . C
C22 0.2049(2) 0.3036(4) 0.6726(2) 0.032(2) Uani d . 1 . C
C221 0.2882(2) 0.2964(4) 0.6978(2) 0.040(2) Uani d D 1 . C
F221 0.30930(15) 0.3911(3) 0.74770(15) 0.060(2) Uani d D 1 . F
F222 0.33214(13) 0.3044(3) 0.63867(14) 0.0591(13) Uani d D 1 . F
F223 0.30476(14) 0.1825(3) 0.7335(2) 0.0578(14) Uani d D 1 . F
C23 0.1647(2) 0.1855(4) 0.6723(2) 0.035(2) Uani d . 1 . C
H23 0.1894(2) 0.1072(4) 0.6845(2) 0.042 Uiso calc R 1 . H
C24 0.0876(2) 0.1842(4) 0.6538(2) 0.036(2) Uani d D 1 . C
C241 0.0461(2) 0.0544(4) 0.6515(2) 0.051(3) Uani d D 1 . C
F241 -0.0274(2) 0.0691(3) 0.6445(4) 0.085(2) Uani d PD 0.860(7) 1 F
F242 0.0685(3) -0.0254(4) 0.5990(3) 0.095(4) Uani d PD 0.860(7) 1 F
F243 0.0572(2) -0.0113(4) 0.7191(2) 0.068(3) Uani d PD 0.860(7) 1 F
F244 0.0902(8) -0.0451(10) 0.6344(17) 0.085(2) Uani d PD 0.140(7) 2 F
F245 0.0120(15) 0.0249(18) 0.7119(9) 0.095(4) Uani d PD 0.140(7) 2 F
F246 -0.0058(11) 0.0567(16) 0.5918(11) 0.068(3) Uani d PD 0.140(7) 2 F
C25 0.0501(2) 0.3023(4) 0.6376(2) 0.035(2) Uani d . 1 . C
H25 -0.0014(2) 0.3019(4) 0.6274(2) 0.042 Uiso calc R 1 . H
C26 0.0895(2) 0.4212(4) 0.6365(2) 0.030(2) Uani d . 1 . C
C261 0.0449(2) 0.5467(4) 0.6191(2) 0.038(2) Uani d . 1 . C
F261 -0.02983(12) 0.5217(3) 0.6135(2) 0.0489(12) Uani d . 1 . F
F262 0.05591(14) 0.6402(2) 0.6726(2) 0.0492(14) Uani d . 1 . F
F263 0.06092(13) 0.5995(2) 0.55039(14) 0.0470(14) Uani d . 1 . F
S3 0.20796(5) 0.72672(10) 0.50009(6) 0.0355(5) Uani d . 1 . S
C31 0.2775(2) 0.7765(4) 0.4347(2) 0.030(2) Uani d . 1 . C
C32 0.3377(2) 0.8588(4) 0.4615(2) 0.031(2) Uani d . 1 . C
C321 0.3409(2) 0.9212(4) 0.5411(2) 0.040(3) Uani d . 1 . C
F321 0.2797(2) 0.9954(2) 0.55249(15) 0.052(2) Uani d . 1 . F
F322 0.4002(2) 1.0021(3) 0.55167(15) 0.059(2) Uani d . 1 . F
F323 0.3463(2) 0.8321(2) 0.59911(13) 0.050(2) Uani d . 1 . F
C33 0.3961(2) 0.8866(4) 0.4139(2) 0.031(2) Uani d . 1 . C
H33 0.4361(2) 0.9383(4) 0.4321(2) 0.038 Uiso calc R 1 . H
C34 0.3946(2) 0.8369(4) 0.3391(2) 0.034(2) Uani d D 1 . C
C341 0.4593(2) 0.8614(4) 0.2889(2) 0.045(2) Uani d D 1 . C
F341 0.4887(4) 0.9801(5) 0.2991(5) 0.103(4) Uani d PD 0.777(5) 1 F
F342 0.5143(3) 0.7784(7) 0.3037(4) 0.102(2) Uani d PD 0.777(5) 1 F
F343 0.4404(2) 0.8516(10) 0.2154(2) 0.102(2) Uani d PD 0.777(5) 1 F
F344 0.4726(14) 0.7590(15) 0.2444(15) 0.103(4) Uani d PD 0.223(5) 2 F
F345 0.4467(10) 0.961(2) 0.2411(14) 0.102(2) Uani d PD 0.223(5) 2 F
F346 0.5225(6) 0.887(3) 0.3272(6) 0.102(2) Uani d PD 0.223(5) 2 F
C35 0.3330(2) 0.7639(4) 0.3105(2) 0.034(2) Uani d . 1 . C
H35 0.3310(2) 0.7346(4) 0.2600(2) 0.041 Uiso calc R 1 . H
C36 0.2746(2) 0.7349(4) 0.3572(2) 0.032(2) Uani d . 1 . C
C361 0.2070(2) 0.6631(4) 0.3196(2) 0.040(2) Uani d . 1 . C
F361 0.2145(2) 0.6448(3) 0.24294(14) 0.057(2) Uani d . 1 . F
F362 0.1965(2) 0.5425(3) 0.34738(15) 0.059(2) Uani d . 1 . F
F363 0.14385(15) 0.7312(3) 0.3245(2) 0.0683(15) Uani d . 1 . F
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'IntTabC Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'IntTablC Tables 4.2.6.8 and 6.1.1.4'
F F .0171 .0103 'IntTablC Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .1234 'IntTablC 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
_geom_angle_publ_flag
C16 C1 S2 . . 117.4(2) yes
C16 C1 S3 . . 118.2(2) yes
S2 C1 S3 . . 104.0(2) yes
C16 C1 S1 . . 88.0(2) yes
S2 C1 S1 . . 114.4(2) yes
S3 C1 S1 . . 115.0(2) yes
C11 S1 C1 . . 74.4(2) yes
C12 C11 C16 . . 122.7(3) yes
C12 C11 S1 . . 139.2(3) yes
C16 C11 S1 . . 98.1(3) yes
C11 C12 C13 . . 115.9(3) yes
C11 C12 C121 . . 120.8(3) yes
C13 C12 C121 . . 123.3(4) ?
F123 C121 F121 . . 105.5(4) ?
F123 C121 F122 . . 106.9(4) ?
F121 C121 F122 . . 106.4(4) ?
F123 C121 C12 . . 112.3(3) ?
F121 C121 C12 . . 112.3(4) ?
F122 C121 C12 . . 113.0(4) ?
C14 C13 C12 . . 121.6(3) yes
C13 C14 C15 . . 121.7(3) yes
C13 C14 C141 . . 120.3(3) ?
C15 C14 C141 . . 118.0(3) ?
F141 C141 F142 . . 108.4(4) ?
F141 C141 F143 . . 106.0(4) ?
F142 C141 F143 . . 104.3(3) ?
F144 C141 F146 . . 104.7(7) ?
F145 C141 F146 . . 104.1(7) ?
F143 C141 F146 . . 135.4(6) ?
F141 C141 C14 . . 112.3(3) ?
F144 C141 C14 . . 114.4(6) ?
F145 C141 C14 . . 114.1(6) ?
F142 C141 C14 . . 113.2(3) ?
F143 C141 C14 . . 112.0(3) ?
F146 C141 C14 . . 112.5(5) ?
C16 C15 C14 . . 115.9(3) yes
C15 C16 C11 . . 122.1(3) yes
C15 C16 C1 . . 138.4(3) yes
C11 C16 C1 . . 99.5(3) yes
C21 S2 C1 . . 104.3(2) yes
C22 C21 C26 . . 118.0(3) ?
C22 C21 S2 . . 122.7(3) ?
C26 C21 S2 . . 119.3(3) ?
C23 C22 C21 . . 120.4(3) ?
C23 C22 C221 . . 116.8(3) ?
C21 C22 C221 . . 122.7(3) ?
F222 C221 F221 . . 107.6(3) ?
F222 C221 F223 . . 106.7(3) ?
F221 C221 F223 . . 105.7(3) ?
F222 C221 C22 . . 112.4(3) ?
F221 C221 C22 . . 112.8(3) ?
F223 C221 C22 . . 111.2(3) ?
C22 C23 C24 . . 120.6(4) ?
C25 C24 C23 . . 119.7(4) ?
C25 C24 C241 . . 120.9(3) ?
C23 C24 C241 . . 119.4(3) ?
F242 C241 F241 . . 110.3(4) ?
F245 C241 F244 . . 108.9(7) ?
F245 C241 F246 . . 107.3(7) ?
F244 C241 F246 . . 103.3(7) ?
F242 C241 F243 . . 105.6(4) ?
F241 C241 F243 . . 103.4(4) ?
F245 C241 C24 . . 115.9(6) ?
F242 C241 C24 . . 113.0(4) ?
F241 C241 C24 . . 112.9(3) ?
F244 C241 C24 . . 111.9(6) ?
F246 C241 C24 . . 108.6(6) ?
F243 C241 C24 . . 111.0(3) ?
C24 C25 C26 . . 120.5(3) ?
C25 C26 C21 . . 120.5(3) ?
C25 C26 C261 . . 117.8(3) ?
C21 C26 C261 . . 121.7(3) ?
F262 C261 F261 . . 106.8(3) ?
F262 C261 F263 . . 107.7(3) ?
F261 C261 F263 . . 105.4(3) ?
F262 C261 C26 . . 113.5(3) ?
F261 C261 C26 . . 111.1(3) ?
F263 C261 C26 . . 111.8(3) ?
C31 S3 C1 . . 102.1(2) yes
C36 C31 C32 . . 118.5(3) ?
C36 C31 S3 . . 122.0(3) ?
C32 C31 S3 . . 119.5(3) ?
C33 C32 C31 . . 120.0(3) ?
C33 C32 C321 . . 117.7(3) ?
C31 C32 C321 . . 122.2(3) ?
F322 C321 F321 . . 106.2(3) ?
F322 C321 F323 . . 106.3(3) ?
F321 C321 F323 . . 106.7(3) ?
F322 C321 C32 . . 111.6(3) ?
F321 C321 C32 . . 112.1(3) ?
F323 C321 C32 . . 113.5(3) ?
C34 C33 C32 . . 120.3(3) ?
C35 C34 C33 . . 119.9(4) ?
C35 C34 C341 . . 119.7(3) ?
C33 C34 C341 . . 120.4(3) ?
F342 C341 F343 . . 107.1(4) ?
F342 C341 F341 . . 105.7(4) ?
F343 C341 F341 . . 106.3(4) ?
F346 C341 F345 . . 106.3(7) ?
F346 C341 F344 . . 106.2(6) ?
F345 C341 F344 . . 105.2(6) ?
F346 C341 C34 . . 113.9(5) ?
F342 C341 C34 . . 111.7(3) ?
F343 C341 C34 . . 113.0(3) ?
F341 C341 C34 . . 112.6(3) ?
F345 C341 C34 . . 112.4(5) ?
F344 C341 C34 . . 112.2(5) ?
C36 C35 C34 . . 120.4(4) ?
C35 C36 C31 . . 120.5(3) ?
C35 C36 C361 . . 116.9(3) ?
C31 C36 C361 . . 122.6(3) ?
F363 C361 F362 . . 108.5(4) ?
F363 C361 F361 . . 105.3(3) ?
F362 C361 F361 . . 104.7(3) ?
F363 C361 C36 . . 112.3(4) ?
F362 C361 C36 . . 114.0(3) ?
F361 C361 C36 . . 111.5(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C16 . 1.513(5) yes
C1 S2 . 1.834(4) yes
C1 S3 . 1.842(4) yes
C1 S1 . 1.897(4) yes
S1 C11 . 1.759(4) yes
C11 C12 . 1.378(5) yes
C11 C16 . 1.383(5) yes
C12 C13 . 1.395(5) yes
C12 C121 . 1.487(5) ?
C121 F123 . 1.311(5) ?
C121 F121 . 1.313(5) ?
C121 F122 . 1.322(5) ?
C13 C14 . 1.387(5) yes
C14 C15 . 1.407(5) yes
C14 C141 . 1.494(5) ?
C141 F141 . 1.296(4) ?
C141 F144 . 1.305(7) ?
C141 F145 . 1.311(7) ?
C141 F142 . 1.313(4) ?
C141 F143 . 1.318(4) ?
C141 F146 . 1.324(7) ?
C15 C16 . 1.375(5) yes
S2 C21 . 1.789(4) yes
C21 C22 . 1.407(5) ?
C21 C26 . 1.409(5) ?
C22 C23 . 1.385(5) ?
C22 C221 . 1.517(5) ?
C221 F222 . 1.321(4) ?
C221 F221 . 1.325(4) ?
C221 F223 . 1.328(4) ?
C23 C24 . 1.385(5) ?
C24 C25 . 1.383(5) ?
C24 C241 . 1.498(6) ?
C241 F245 . 1.271(7) ?
C241 F242 . 1.291(5) ?
C241 F241 . 1.311(5) ?
C241 F244 . 1.314(7) ?
C241 F246 . 1.344(7) ?
C241 F243 . 1.347(5) ?
C25 C26 . 1.386(5) ?
C26 C261 . 1.511(5) ?
C261 F262 . 1.326(5) ?
C261 F261 . 1.345(5) ?
C261 F263 . 1.346(5) ?
S3 C31 . 1.790(4) yes
C31 C36 . 1.402(5) ?
C31 C32 . 1.407(5) ?
C32 C33 . 1.386(5) ?
C32 C321 . 1.510(5) ?
C321 F322 . 1.335(5) ?
C321 F321 . 1.339(5) ?
C321 F323 . 1.345(5) ?
C33 C34 . 1.386(5) ?
C34 C35 . 1.384(5) ?
C34 C341 . 1.497(5) ?
C341 F346 . 1.296(6) ?
C341 F342 . 1.298(5) ?
C341 F343 . 1.299(4) ?
C341 F341 . 1.311(5) ?
C341 F345 . 1.312(6) ?
C341 F344 . 1.314(6) ?
C35 C36 . 1.378(6) ?
C36 C361 . 1.514(5) ?
C361 F363 . 1.318(5) ?
C361 F362 . 1.322(5) ?
C361 F361 . 1.352(5) ?
