High Z’ structures of 1,2,3,5-dithiadiazolyls and of 1,2,3,5-diselenadiazolyls containing the first structurally characterized monomeric diselenadiazolyls
Boeré, René; Hill, Nathan D. D.; CrystEngComm  (2017) –; doi:10.1039/C7CE00863E

data_7228525
_publ_section_title
;
 High Z&#x2019; structures of 1,2,3,5-dithiadiazolyls and of
 1,2,3,5-diselenadiazolyls containing the first structurally characterized
 monomeric diselenadiazolyls
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE00863E
_journal_year                    2017
_chemical_compound_source        No.
_chemical_formula_moiety         'C8 H4 F3 N2 S2'
_chemical_formula_sum            'C8 H4 F3 N2 S2'
_chemical_formula_weight         249.25
_chemical_melting_point          415
_chemical_name_systematic
4-[3-(trifluoromethyl)phenyl]-3H-1,2,3,5-Dithiadiazol-3-yl
_chemical_properties_physical
', Air-sensitive,Oxygen-sensitive, Oxygen-sensitive'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-10-27
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2017-06-19 deposited with the CCDC.
2017-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                108.455(2)
_cell_angle_beta                 91.6884(17)
_cell_angle_gamma                98.597(2)
_cell_formula_units_Z            12
_cell_length_a                   7.12511(16)
_cell_length_b                   16.8803(4)
_cell_length_c                   24.7194(5)
_cell_measurement_reflns_used    19598
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      77.3510
_cell_measurement_theta_min      5.4110
_cell_volume                     2779.15(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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      100.00(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200/300K'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -108.00 -33.00   0.50    0.75    --  -38.50 -19.00 150.00  150
  2  \w    -50.00  25.00   0.50    0.75    --  -38.50  57.00  30.00  150
  3  \w    -44.00  31.00   0.50    0.75    --  -38.50  19.00 -60.00  150
  4  \w    -44.00  31.00   0.50    0.75    --  -38.50  19.00   0.00  150
  5  \w     23.00 100.00   0.50    0.75    --   48.81-125.00 150.00  154
  6  \w     93.00 169.00   0.50    2.99    --  106.38  61.00-180.00  152
  7  \w     41.00 122.00   0.50    2.99    --  106.38-125.00 120.00  162
  8  \w     38.00 115.00   0.50    2.99    --  106.38 -15.00-120.00  154
  9  \w     42.00 111.00   0.50    2.99    --  106.38 -45.00  60.00  138
 10  \w     42.00 130.00   0.50    2.99    --  106.38 -77.00 -60.00  176
 11  \w     38.00 110.00   0.50    2.99    --  106.38 -30.00-180.00  144
 12  \w     38.00 110.00   0.50    2.99    --  106.38 -30.00   0.00  144
 13  \w     38.00 110.00   0.50    2.99    --  106.38 -30.00 -60.00  144
 14  \w     38.00 109.00   0.50    2.99    --  106.38 -94.00-150.00  142
 15  \w     38.00 109.00   0.50    2.99    --  106.38 -94.00 -60.00  142
 16  \w     38.00 109.00   0.50    2.99    --  106.38 -94.00-180.00  142
 17  \w     38.00 115.00   0.50    2.99    --  106.38 -15.00  90.00  154
 18  \w    102.00 171.00   0.50    2.99    --  106.38  45.00 120.00  138
 19  \w     38.00 115.00   0.50    2.99    --  106.38 -15.00 150.00  154
 20  \w     25.00 113.00   0.50    0.75    --   48.81  77.00 -60.00  176
 21  \w     25.00 113.00   0.50    0.75    --   48.81  77.00  30.00  176
 22  \w     25.00 113.00   0.50    0.75    --   48.81  77.00 120.00  176
 23  \w     25.00 113.00   0.50    0.75    --   48.81  77.00-120.00  176
 24  \w     83.00 171.00   0.50    2.99    --  106.38  77.00 -90.00  176
 25  \w    103.00 175.00   0.50    2.99    --  106.38  30.00-120.00  144
 26  \w     98.00 175.00   0.50    2.99    --  106.38  15.00   0.00  154
 27  \w     83.00 171.00   0.50    2.99    --  106.38  77.00   0.00  176
 28  \w     98.00 175.00   0.50    2.99    --  106.38  15.00 -60.00  154
 29  \w     93.00 169.00   0.50    2.99    --  106.38  61.00  90.00  152
 30  \w     93.00 169.00   0.50    2.99    --  106.38  61.00 150.00  152
 31  \w     83.00 171.00   0.50    2.99    --  106.38  77.00  30.00  176
 32  \w     83.00 171.00   0.50    2.99    --  106.38  77.00 -60.00  176
 33  \w     83.00 171.00   0.50    2.99    --  106.38  77.00-120.00  176
 34  \w     83.00 171.00   0.50    2.99    --  106.38  77.00 120.00  176
 35  \w     83.00 171.00   0.50    2.99    --  106.38  77.00  60.00  176
 36  \w     37.00 112.00   0.50    0.75    --   48.81  57.00   0.00  150
 37  \w     25.00 113.00   0.50    0.75    --   48.81  77.00  90.00  176
 38  \w     25.00 113.00   0.50    0.75    --   48.81  77.00-180.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at zero, Pilatus 200/300K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0216779000
_diffrn_orient_matrix_UB_12      -0.0912923000
_diffrn_orient_matrix_UB_13      0.0018015000
_diffrn_orient_matrix_UB_21      0.0049648000
_diffrn_orient_matrix_UB_22      -0.0335195000
_diffrn_orient_matrix_UB_23      -0.0655143000
_diffrn_orient_matrix_UB_31      0.2182790000
_diffrn_orient_matrix_UB_32      0.0081254000
_diffrn_orient_matrix_UB_33      0.0070935000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            51041
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         77.626
_diffrn_reflns_theta_min         3.783
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.398
_exptl_absorpt_correction_T_max  0.857
_exptl_absorpt_correction_T_min  0.625
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic violet'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_description       plate
_exptl_crystal_F_000             1500
_exptl_crystal_preparation       'Previously published.'
_exptl_crystal_recrystallization_method Sublimation
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.063
_refine_diff_density_max         0.927
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     811
_refine_ls_number_reflns         11371
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0650
_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/[\s^2^(Fo^2^)+(0.0605P)^2^+13.7823P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1609
_refine_ls_wR_factor_ref         0.1678
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9705
_reflns_number_total             11371
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00863e2.cif
_cod_data_source_block           2
_cod_original_cell_volume        2779.16(12)
_cod_database_code               7228525
_chemical_oxdiff_formula         'C8 H4 F3 N2 S2'
_chemical_oxdiff_usercomment     'From a mp capillary labelled m-CF3 dimer'
_reflns_odcompleteness_completeness 99.61
_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:
 C11(H11), C13(H13), C14(H14), C15(H15), C51(H51), C53(H53), C54(H54),
 C55(H55), C41(H41), C43(H43), C44(H44), C45(H45), C22(H22), C24(H24), C25(H25),
  C26(H26), C61(H61), C63(H63), C64(H64), C65(H65), C31(H31), C33(H33),
 C34(H34), C35(H35)
;
_shelx_res_checksum              90228
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method
'MiTeGen 100um polymer mount, with ParatoneTM oil.'
_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 2.102
_oxdiff_exptl_absorpt_empirical_full_min 0.503