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_7251099
_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         'C6 F4 I2, 2(C7 H5 N S)'
_chemical_formula_sum            'C20 H10 F4 I2 N2 S2'
_chemical_formula_weight         672.22
_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             2025-01-28
_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                 97.600(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.4312(5)
_cell_length_b                   4.2982(2)
_cell_length_c                   23.6454(10)
_cell_measurement_reflns_used    4501
_cell_measurement_temperature    173
_cell_measurement_theta_max      29.8430
_cell_measurement_theta_min      3.0640
_cell_volume                     1050.84(8)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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   -103.00 -10.00   0.50    0.50    --  -13.20  28.00 120.00  186
  2  \w     13.00  76.00   0.50    0.50    --  -13.20  28.00 120.00  126
  3  \w   -103.00 -77.00   0.50    0.50    --  -13.20  28.00  30.00   52
  4  \w     38.00  76.00   0.50    0.50    --  -13.20  28.00  30.00   76
  5  \w    -84.00   5.00   0.50    0.50    --  -13.20  18.00  30.00  178
;
_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      0.0410972000
_diffrn_orient_matrix_UB_12      -0.0601442000
_diffrn_orient_matrix_UB_13      -0.0189816000
_diffrn_orient_matrix_UB_21      0.0525517000
_diffrn_orient_matrix_UB_22      0.0005190000
_diffrn_orient_matrix_UB_23      0.0223408000
_diffrn_orient_matrix_UB_31      -0.0159732000
_diffrn_orient_matrix_UB_32      -0.1536880000
_diffrn_orient_matrix_UB_33      0.0074963000
_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  0.0214
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            6963
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         3.053
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_exptl_absorpt_coefficient_mu    3.237
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44407
_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    2.124
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.445
_exptl_crystal_size_min          0.132
_refine_diff_density_max         0.934
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0217
_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^)+(0.0257P)^2^+0.8871P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0556
_refine_ls_wR_factor_ref         0.0571
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2212
_reflns_number_total             2419
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00645g2.cif
_cod_data_source_block           btz-c6f4i2_auto
_cod_depositor_comments
'Adding full bibliography for 7251097--7251099.cif.'
_cod_database_code               7251099
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         C20H10F4I2N2S2
_shelx_estimated_absorpt_t_max   0.678
_shelx_estimated_absorpt_t_min   0.312
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00E(H00E)
;
_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 1.386
_oxdiff_exptl_absorpt_empirical_full_min 0.679