The crystal structure of 2,5-bis(3,5-dimethylphenyl)thiazolo[5,4-d]thiazole, C20H18N2S2
Zhai, Zhi-Wei; Yang, Shuang-Hua; Zeitschrift für Kristallographie - New Crystal Structures 236 (2021) 1031–1033; doi:10.1515/ncrs-2021-0213

data_8104658
_publ_section_title
;
 The crystal structure of
 2,5-bis(3,5-dimethylphenyl)thiazolo[5,4-d]thiazole, C20H18N2S2
;
_journal_issue                   5
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              1031
_journal_page_last               1033
_journal_paper_doi               10.1515/ncrs-2021-0213
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C10 H9 N S'
_chemical_formula_sum            'C10 H9 N S'
_chemical_formula_weight         175.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_cell_angle_alpha                90
_cell_angle_beta                 90.592(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.92140(10)
_cell_length_b                   6.08080(10)
_cell_length_c                   17.8091(3)
_cell_measurement_reflns_used    2731
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      72.6700
_cell_measurement_theta_min      4.9620
_cell_volume                     857.79(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.962
_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     28.00  64.00   0.50    0.50    --    0.00  82.00 -60.00   72
  2  \w     23.00  77.00   0.50    0.50    --    0.00  38.00-180.00  108
  3  \w    -16.00   9.00   0.50    0.50    --    0.00  82.00 -60.00   50
  4  \w    -27.00  12.00   0.50    0.50    --    0.00  38.00-180.00   78
  5  \w     64.00 114.00   0.50    0.50    --   97.60 -61.00  90.00  100
  6  \w      9.00  54.00   0.50    0.50    --   97.60 -77.00 -60.00   90
  7  \w     72.00 126.00   0.50    0.50    --   97.60 -45.00-120.00  108
  8  \w     60.00 134.00   0.50    0.50    --   97.60  82.00 -90.00  148
  9  \w     27.00  53.00   0.50    0.50    --   97.60 -45.00-120.00   52
 10  \w     11.00  36.00   0.50    0.50    --   97.60 -61.00  90.00   50
 11  \w     96.00 132.00   0.50    0.50    --   97.60 -77.00 -60.00   72
 12  \w     60.00  86.00   0.50    0.50    --   97.60 -77.00 -60.00   52
 13  \w     14.00 129.00   0.50    0.50    --   97.60 -77.00 120.00  230
 14  \w     80.00 149.00   0.50    0.50    --   97.60 -15.00  30.00  138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0331988000
_diffrn_orient_matrix_UB_12      0.2405363000
_diffrn_orient_matrix_UB_13      0.0227480000
_diffrn_orient_matrix_UB_21      0.1658454000
_diffrn_orient_matrix_UB_22      0.0019747000
_diffrn_orient_matrix_UB_23      0.0459618000
_diffrn_orient_matrix_UB_31      0.0959384000
_diffrn_orient_matrix_UB_32      0.0794920000
_diffrn_orient_matrix_UB_33      -0.0696966000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3637
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.160
_diffrn_reflns_theta_min         4.967
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.820
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1658
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0516P)^2^+0.6979P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1051
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1583
_reflns_number_total             1658
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0213_suppl.cif
_cod_data_source_block           metz
_cod_database_code               8104658
_shelx_estimated_absorpt_t_max   0.920
_shelx_estimated_absorpt_t_min   0.766
_reflns_odcompleteness_completeness 99.41
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C1, N1, C2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C8(H8)
3.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;