#------------------------------------------------------------------------------
#$Date: 2019-11-10 20:18:05 +0200 (Sun, 10 Nov 2019) $
#$Revision: 226159 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/61/4516168.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4516168
loop_
_publ_author_name
'Boeré, René T'
_publ_section_title
;
 Experimental and Computational Evidence for "Double Pancake
 Bonds": The Role of Dispersion-Corrected DFT Methods in Strongly
 Dimerized 5-Aryl-1λ²,3λ²-dithia-2,4,6-triazines.
;
_journal_issue                   12
_journal_name_full               'ACS omega'
_journal_page_first              18170
_journal_page_last               18180
_journal_paper_doi               10.1021/acsomega.8b03211
_journal_volume                  3
_journal_year                    2018
_chemical_formula_moiety         'C8 H4 F3 N5 S3'
_chemical_formula_sum            'C8 H4 F3 N5 S3'
_chemical_formula_weight         323.34
_chemical_melting_point          386
_chemical_name_common
;
 mCF3-bicyclic
;
_chemical_name_systematic
;
 7-[3-(Trifluoromethyl)phenyl]-1l4,3l4,5l4-trithia-2,4,6,8,9-pentaazabicyclo
 [3.3.1]nona-1(9),2,3,5,7-pentaene
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.6781(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.90772(16)
_cell_length_b                   4.66989(3)
_cell_length_c                   22.2724(2)
_cell_measurement_reflns_used    19022
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      77.1460
_cell_measurement_theta_min      4.0260
_cell_volume                     2282.39(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200/300K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -71.00  -1.00   0.50    0.50    --   -4.52 -38.00 -60.00  140
  2  ω    -16.00  59.00   0.50    0.50    --   -4.52  57.00-150.00  150
  3  ω    -29.00  25.00   0.50    0.50    --    4.52  95.00  82.00  108
  4  ω    -30.00  22.00   0.50    0.50    --    4.52  97.00 -16.00  104
  5  ω     37.00 109.00   0.50    1.09    --  105.46 -94.00 -90.00  144
  6  ω    101.00 170.00   0.50    1.09    --  105.46  45.00-150.00  138
  7  ω     82.00 170.00   0.50    1.09    --  105.46  77.00 -30.00  176
  8  ω     37.00 109.00   0.50    1.09    --  105.46 -94.00-150.00  144
  9  ω    102.00 174.00   0.50    1.09    --  105.46  30.00 -90.00  144
 10  ω    102.00 174.00   0.50    1.09    --  105.46  30.00 -60.00  144
 11  ω     37.00 109.00   0.50    1.09    --  105.46 -30.00 -90.00  144
 12  ω     41.00 110.00   0.50    1.09    --  105.46 -45.00 -90.00  138
 13  ω     43.00 119.00   0.50    1.09    --  105.46 -61.00-150.00  152
 14  ω     43.00 119.00   0.50    1.09    --  105.46 -61.00 -90.00  152
 15  ω     82.00 170.00   0.50    1.09    --  105.46  77.00 -60.00  176
 16  ω     -7.00  68.00   0.50    0.50    --    4.52  57.00 150.00  150
 17  ω      1.00  71.00   0.50    0.50    --    4.52  38.00 -90.00  140
 18  ω    -64.00  10.00   0.50    0.50    --    4.52 -19.00 120.00  148
 19  ω    102.00 174.00   0.50    1.09    --  105.46  30.00  30.00  144
 20  ω    102.00 174.00   0.50    1.09    --  105.46  30.00-120.00  144
 21  ω     97.00 174.00   0.50    1.09    --  105.46  15.00 150.00  154
 22  ω     43.00 119.00   0.50    1.09    --  105.46 -61.00  30.00  152
 23  ω     40.00 122.00   0.50    1.09    --  105.46-125.00 120.00  164
 24  ω     82.00 170.00   0.50    1.09    --  105.46  77.00  90.00  176
 25  ω     82.00 170.00   0.50    1.09    --  105.46  77.00  30.00  176
 26  ω     82.00 170.00   0.50    1.09    --  105.46  77.00-180.00  176
 27  ω     97.00 174.00   0.50    1.09    --  105.46  15.00  90.00  154
 28  ω    -39.00  22.00   0.50    0.50    --   -4.52  97.00 -16.00  122
 29  ω    -19.00  69.00   0.50    0.50    --    4.52  77.00-120.00  176
 30  ω    -64.00  10.00   0.50    0.50    --    4.52 -19.00  60.00  148
 31  ω     82.00 170.00   0.50    1.09    --  105.46  77.00 120.00  176
 32  ω     97.00 174.00   0.50    1.09    --  105.46  15.00 -30.00  154
 33  ω     82.00 170.00   0.50    1.09    --  105.46  77.00  60.00  176
 34  ω     82.00 170.00   0.50    1.09    --  105.46  77.00 -90.00  176
 35  ω     92.00 168.00   0.50    1.09    --  105.46  61.00   0.00  152
 36  ω     82.00 170.00   0.50    1.09    --  105.46  77.00-120.00  176
 37  ω     82.00 170.00   0.50    1.09    --  105.46  77.00-150.00  176
 38  ω     37.00 109.00   0.50    1.09    --  105.46 -94.00-180.00  144
 39  ω     82.00 170.00   0.50    1.09    --  105.46  77.00 150.00  176
 40  ω    -19.00  69.00   0.50    0.50    --    4.52  77.00 120.00  176
 41  ω    -64.00  10.00   0.50    0.50    --    4.52 -19.00-180.00  148
 42  ω    -64.00  10.00   0.50    0.50    --    4.52 -19.00 -60.00  148
 43  ω     82.00 170.00   0.50    1.09    --  105.46  77.00   0.00  176
 44  ω     97.00 174.00   0.50    1.09    --  105.46  15.00-150.00  154
 45  ω     40.00  92.00   0.50    1.09    --  105.46-125.00  90.00  104
 46  ω    101.00 170.00   0.50    1.09    --  105.46  45.00  30.00  138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0583550000
_diffrn_orient_matrix_UB_12      0.1015329000
_diffrn_orient_matrix_UB_13      0.0147907000
_diffrn_orient_matrix_UB_21      -0.0297820000
_diffrn_orient_matrix_UB_22      -0.2934491000
_diffrn_orient_matrix_UB_23      -0.0205413000
_diffrn_orient_matrix_UB_31      0.0252710000
_diffrn_orient_matrix_UB_32      -0.1114735000
_diffrn_orient_matrix_UB_33      0.0676113000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            23650
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.607
_diffrn_reflns_theta_min         4.029
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.306
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.882
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_preparation
'From 3-CF3C6H4CN(SiMe,)2NS and S3N3Cl3 in hot CH3CN.'
_exptl_crystal_recrystallization_method 'Cooling a hot CH3CN solution.'
_exptl_crystal_size_max          0.385
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.063
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2390
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0399P)²+3.9061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0744
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2373
_reflns_number_total             2390
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao8b03211_si_002.cif
_cod_data_source_block           4
_cod_database_code               4516168
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C8H4F3N5S3
_chemical_oxdiff_usercomment
'Nice yellow to orange needles. Large, had to cut this block. In mp capillary.'
_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.
;
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7)
;
_olex2_exptl_crystal_mounting_method 'MiTeGen-100um loop in Paratone TM oil.'
_olex2_submission_original_sample_id RB16083rf1
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.759
_oxdiff_exptl_absorpt_empirical_full_min 0.740
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_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
S2 S 0.33813(2) 0.25429(8) 0.54931(2) 0.01645(11) Uani 1 1 d .
S1 S 0.45132(2) 0.25537(8) 0.53422(2) 0.01468(11) Uani 1 1 d .
S3 S 0.43179(2) 0.56373(8) 0.63724(2) 0.01641(11) Uani 1 1 d .
F1 F 0.45707(5) 0.9676(3) 0.30218(5) 0.0323(3) Uani 1 1 d .
F2 F 0.40472(5) 1.3499(2) 0.27259(5) 0.0286(2) Uani 1 1 d .
F3 F 0.37805(5) 0.9586(2) 0.22198(5) 0.0297(3) Uani 1 1 d .
N2 N 0.39762(6) 0.0636(3) 0.54895(6) 0.0178(3) Uani 1 1 d .
N1 N 0.42287(6) 0.4760(3) 0.47726(6) 0.0166(3) Uani 1 1 d .
N3 N 0.32107(6) 0.4735(3) 0.49053(6) 0.0176(3) Uani 1 1 d .
N5 N 0.36344(6) 0.4840(3) 0.61327(6) 0.0186(3) Uani 1 1 d .
N4 N 0.47572(6) 0.4839(3) 0.59849(6) 0.0171(3) Uani 1 1 d .
C1 C 0.36366(7) 0.5475(3) 0.46308(7) 0.0144(3) Uani 1 1 d .
C2 C 0.34185(7) 0.7392(3) 0.40755(7) 0.0146(3) Uani 1 1 d .
C3 C 0.38027(7) 0.8058(3) 0.37079(7) 0.0152(3) Uani 1 1 d .
H3 H 0.418829 0.724034 0.379645 0.018 Uiso 1 1 calc R
C4 C 0.36048(7) 0.9942(3) 0.32111(7) 0.0159(3) Uani 1 1 d .
C5 C 0.30260(7) 1.1180(4) 0.30704(7) 0.0191(3) Uani 1 1 d .
H5 H 0.289924 1.246372 0.273911 0.023 Uiso 1 1 calc R
C6 C 0.26419(7) 1.0476(4) 0.34297(8) 0.0203(3) Uani 1 1 d .
H6 H 0.225397 1.127214 0.333576 0.024 Uiso 1 1 calc R
C7 C 0.28348(7) 0.8591(4) 0.39281(7) 0.0180(3) Uani 1 1 d .
H7 H 0.257468 0.811982 0.416591 0.022 Uiso 1 1 calc R
C8 C 0.40017(7) 1.0672(3) 0.28007(7) 0.0179(3) Uani 1 1 d .
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'
F F 0.0727 0.0534 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 -1 0.0866
1 0 1 0.0866
-1 0 1 0.0535
1 0 -1 0.0535
-1 0 -1 0.0501
1 0 1 0.0501
1 -1 -1 0.0987
0 1 1 0.1287
-1 1 -1 0.1416
-5 0 -1 0.0701
5 0 1 0.0701
1 0 -1 0.0560
-1 0 1 0.0560
-1 0 -1 0.0659
1 0 1 0.0659
-8 1 -8 0.0981
-12 0 12 0.0562
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 S2 N5 104.93(7)
N3 S2 N2 110.47(7)
N3 S2 N5 102.60(7)
N2 S1 N4 104.70(7)
N1 S1 N2 110.49(7)
N1 S1 N4 102.46(7)
N4 S3 N5 120.33(8)
S1 N2 S2 112.43(8)
C1 N1 S1 119.64(11)
C1 N3 S2 119.65(11)
S3 N5 S2 119.73(8)
S3 N4 S1 119.92(8)
N1 C1 C2 114.78(13)
N3 C1 N1 130.41(14)
N3 C1 C2 114.80(13)
C3 C2 C1 120.11(13)
C3 C2 C7 119.56(14)
C7 C2 C1 120.31(14)
C2 C3 H3 120.2
C4 C3 C2 119.52(14)
C4 C3 H3 120.2
C3 C4 C5 120.95(14)
C3 C4 C8 120.94(14)
C5 C4 C8 118.10(14)
C4 C5 H5 120.3
C6 C5 C4 119.37(15)
C6 C5 H5 120.3
C5 C6 H6 119.9
C7 C6 C5 120.20(15)
C7 C6 H6 119.9
C2 C7 H7 119.8
C6 C7 C2 120.38(14)
C6 C7 H7 119.8
F1 C8 F2 106.64(13)
F1 C8 F3 106.33(13)
F1 C8 C4 113.16(13)
F2 C8 F3 105.84(13)
F2 C8 C4 112.45(13)
F3 C8 C4 111.90(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S2 N2 1.6296(13)
S2 N3 1.6190(14)
S2 N5 1.7440(15)
S1 N2 1.6292(13)
S1 N1 1.6192(13)
S1 N4 1.7437(14)
S3 N5 1.5478(14)
S3 N4 1.5475(13)
F1 C8 1.3376(19)
F2 C8 1.3388(19)
F3 C8 1.3460(18)
N1 C1 1.3436(19)
N3 C1 1.337(2)
C1 C2 1.492(2)
C2 C3 1.398(2)
C2 C7 1.399(2)
C3 H3 0.9300
C3 C4 1.384(2)
C4 C5 1.397(2)
C4 C8 1.502(2)
C5 H5 0.9300
C5 C6 1.388(2)
C6 H6 0.9300
C6 C7 1.386(2)
C7 H7 0.9300
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
S2 N3 C1 N1 -2.5(2)
S2 N3 C1 C2 177.15(10)
S1 N1 C1 N3 2.9(2)
S1 N1 C1 C2 -176.72(10)
N2 S2 N3 C1 -21.99(15)
N2 S2 N5 S3 25.21(11)
N2 S1 N1 C1 21.22(14)
N2 S1 N4 S3 -25.65(11)
N1 S1 N2 S2 -43.65(10)
N1 S1 N4 S3 89.73(10)
N1 C1 C2 C3 6.7(2)
N1 C1 C2 C7 -171.66(14)
N3 S2 N2 S1 44.03(10)
N3 S2 N5 S3 -90.28(10)
N3 C1 C2 C3 -172.94(14)
N3 C1 C2 C7 8.7(2)
N5 S2 N2 S1 -65.88(9)
N5 S2 N3 C1 89.42(13)
N5 S3 N4 S1 -10.15(13)
N4 S1 N2 S2 66.00(9)
N4 S1 N1 C1 -89.88(13)
N4 S3 N5 S2 10.38(13)
C1 C2 C3 C4 -177.04(13)
C1 C2 C7 C6 176.99(14)
C2 C3 C4 C5 -0.2(2)
C2 C3 C4 C8 -179.08(14)
C3 C2 C7 C6 -1.4(2)
C3 C4 C5 C6 -0.9(2)
C3 C4 C8 F1 -9.2(2)
C3 C4 C8 F2 -130.14(16)
C3 C4 C8 F3 110.88(16)
C4 C5 C6 C7 0.8(2)
C5 C4 C8 F1 171.91(14)
C5 C4 C8 F2 51.00(19)
C5 C4 C8 F3 -67.98(19)
C5 C6 C7 C2 0.3(2)
C7 C2 C3 C4 1.4(2)
C8 C4 C5 C6 178.01(15)
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0008 0.0004 -0.9990 0.0437 0.0502 -0.0929
1.0008 -0.0004 0.9990 -0.0437 -0.0502 0.0929
-0.9990 0.0003 1.0007 0.0731 0.0091 0.0424
0.9990 -0.0003 -1.0007 -0.0731 -0.0091 -0.0424
-1.0008 0.0004 -0.9990 0.0437 0.0502 -0.0929
1.0008 -0.0004 0.9990 -0.0437 -0.0502 0.0929
0.9966 -1.0001 -0.9998 -0.1745 0.2843 0.0691
0.0033 0.9997 0.9989 0.1161 -0.3140 -0.0438
-0.9985 1.0002 -0.9999 0.1450 -0.2432 -0.2043
-5.0005 0.0018 -0.9954 0.2773 0.1689 -0.1939
5.0005 -0.0018 0.9954 -0.2773 -0.1689 0.1939
0.9990 -0.0003 -1.0007 -0.0731 -0.0091 -0.0424
-0.9990 0.0003 1.0007 0.0731 0.0091 0.0424
-1.0008 0.0004 -0.9990 0.0437 0.0502 -0.0929
1.0008 -0.0004 0.9990 -0.0437 -0.0502 0.0929
-8.1908 1.0993 -8.1199 0.4695 0.0882 -0.8785
-11.5739 -0.1833 11.8906 0.8327 0.1542 0.5319
