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_7251098
_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, C7 H F5 O2'
_chemical_formula_sum            'C14 H6 F5 N O2 S'
_chemical_formula_weight         347.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-06-14
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_audit_update_record
;
2025-06-21 deposited with the CCDC.	2025-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.938(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7322(6)
_cell_length_b                   12.9715(5)
_cell_length_c                   8.4476(4)
_cell_measurement_reflns_used    3886
_cell_measurement_temperature    173
_cell_measurement_theta_max      29.6260
_cell_measurement_theta_min      3.5830
_cell_volume                     1364.99(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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -14.00  75.00   0.50    0.50    --  -13.20  46.00   0.00  178
  2  \w     18.00  43.00   0.50    0.50    --  -13.20   9.00  90.00   50
  3  \w    -92.00 -41.00   0.50    0.50    --  -13.20  28.00 -60.00  102
  4  \w      2.00  29.00   0.50    0.50    --  -13.20  28.00 -60.00   54
  5  \w   -102.00  70.00   0.50    0.50    --  -13.20  55.00 -30.00  344
;
_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      -0.0448270000
_diffrn_orient_matrix_UB_12      -0.0274157000
_diffrn_orient_matrix_UB_13      0.0160328000
_diffrn_orient_matrix_UB_21      0.0246430000
_diffrn_orient_matrix_UB_22      -0.0471992000
_diffrn_orient_matrix_UB_23      -0.0141238000
_diffrn_orient_matrix_UB_31      0.0249811000
_diffrn_orient_matrix_UB_32      -0.0027664000
_diffrn_orient_matrix_UB_33      0.0831821000
_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  0.0281
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5471
_diffrn_reflns_point_group_measured_fraction_full 0.782
_diffrn_reflns_point_group_measured_fraction_max 0.747
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.090
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73201
_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    1.690
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 727 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2339
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0292
_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^)+(0.0538P)^2^+0.4298P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0834
_reflns_Friedel_coverage         0.493
_reflns_Friedel_fraction_full    0.564
_reflns_Friedel_fraction_max     0.495
_reflns_number_gt                2253
_reflns_number_total             2339
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00645g2.cif
_cod_data_source_block           btz-pfba_auto
_cod_depositor_comments
'Adding full bibliography for 7251097--7251099.cif.'
_cod_database_code               7251098
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         C14H6F5NO2S
_cell_oxdiff_angle_alpha         89.975(3)
_cell_oxdiff_angle_beta          101.937(3)
_cell_oxdiff_angle_gamma         89.946(3)
_cell_oxdiff_length_a            12.7350(6)
_cell_oxdiff_length_b            12.9781(5)
_cell_oxdiff_length_c            8.4415(3)
_cell_oxdiff_measurement_reflns_used 3886
_cell_oxdiff_volume              1365.00(9)
_shelx_estimated_absorpt_t_max   0.891
_shelx_estimated_absorpt_t_min   0.868
_diffrn_oxdiff_digest_hkl
;
012b50c903e0d5a363c21500e3dedc0950b493
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C1(H1), C8(H8), C9(H9), C7(H7)
2.b Idealised tetrahedral OH refined as rotating group:
 O22(H22)
;
_shelx_res_checksum              4118
_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 1.258
_oxdiff_exptl_absorpt_empirical_full_min 0.814