Co-crystallization of benzothiazole via halogen and hydrogen bonding: crystal structure and photoluminescence properties
Toshima, Ryo; Eguchi, Yuto; Oshima, Ibuki; Yoshino, Riku; Tamano, Natsuki; Fukumoto, Hiroki; Yasui, Motohiro; Konno, Tsutomu; Yamada, Shigeyuki; Morita, Masato; CrystEngComm 27 (2025) 7649–7654; doi:10.1039/D5CE00645G

data_7251097
_publ_section_title
;
 Co-crystallization of benzothiazole via halogen and hydrogen bonding:
 crystal structure and photoluminescence properties
;
_journal_issue                   47
_journal_name_full               CrystEngComm
_journal_page_first              7649
_journal_page_last               7654
_journal_paper_doi               10.1039/D5CE00645G
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C7 H5 N S, C6 H F5 O'
_chemical_formula_sum            'C13 H6 F5 N O S'
_chemical_formula_weight         319.25
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-06-19
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-06-21 deposited with the CCDC.	2025-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.542(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8713(4)
_cell_length_b                   12.7549(6)
_cell_length_c                   14.2974(7)
_cell_measurement_reflns_used    10076
_cell_measurement_temperature    173
_cell_measurement_theta_max      29.1460
_cell_measurement_theta_min      3.1290
_cell_volume                     1242.22(11)
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.928
_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     21.00  46.00   0.50    1.54    --  -13.20  41.00 140.00   50
  2  \w   -103.00 -37.00   0.50    1.54    --  -13.20  41.00 140.00  132
  3  \w     42.00  68.00   0.50    1.54    --    5.00  28.00   0.00   52
  4  \w     48.00  74.00   0.50    1.54    --    5.00  55.00  60.00   52
  5  \w    -19.00   6.00   0.50    1.54    --    5.00  41.00 140.00   50
  6  \w    -18.00  64.00   0.50    1.54    --  -13.20  37.00 -60.00  164
  7  \w    -81.00 -54.00   0.50    1.54    --  -13.20   9.00-180.00   54
  8  \w      0.00  75.00   0.50    1.54    --  -13.20   9.00-180.00  150
  9  \w   -102.00  76.00   0.50    1.54    --  -13.20  37.00   0.00  356
 10  \w    -95.00  65.00   0.50    1.54    --  -13.20  55.00-150.00  320
 11  \w   -103.00 -57.00   0.50    1.54    --  -13.20  37.00 -60.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0902744000
_diffrn_orient_matrix_UB_12      -0.0230168000
_diffrn_orient_matrix_UB_13      -0.0080992000
_diffrn_orient_matrix_UB_21      -0.0492706000
_diffrn_orient_matrix_UB_22      -0.0282447000
_diffrn_orient_matrix_UB_23      -0.0388052000
_diffrn_orient_matrix_UB_31      0.0163844000
_diffrn_orient_matrix_UB_32      0.0420124000
_diffrn_orient_matrix_UB_33      -0.0305289000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21944
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.834
_diffrn_reflns_theta_min         2.874
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.320
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0474
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1470
_refine_ls_wR_factor_ref         0.1533
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2710
_reflns_number_total             3312
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00645g2.cif
_cod_data_source_block           btzh_cocrystal_ethanol_auto
_cod_depositor_comments
'Adding full bibliography for 7251097--7251099.cif.'
_cod_database_code               7251097
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         C13H5S1N1I1F5O1
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.880
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C5(H5), C1(H1), C9(H9)
;
_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 1.421
_oxdiff_exptl_absorpt_empirical_full_min 0.656