Eco-friendly synthesis of highly emissive benzothiadiazole-based fluorophores <i>via</i> a solvent-free hand-grinding Horner-Wadsworth-Emmons reaction in ≤1 minute.
Gnanasekaran, Premkumar; Chen, Chia-Yu; Chu, Ting-Hung; Lin, Po-Heng; Chang, Yuan Jay; Chemical communications (Cambridge, England) 61 (2025) 18148–18151; doi:10.1039/d5cc04892c

data_7135101
_publ_section_title
;
 Eco-friendly synthesis of highly emissive benzothiadiazole-based
 fluorophores <i>via</i> a solvent-free hand-grinding
 Horner-Wadsworth-Emmons reaction in &#x2264;1 minute.
;
_journal_issue                   92
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              18148
_journal_page_last               18151
_journal_paper_doi               10.1039/d5cc04892c
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C22 H16 N2 S'
_chemical_formula_sum            'C22 H16 N2 S'
_chemical_formula_weight         340.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2024-08-13
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-07-22 deposited with the CCDC.	2025-10-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.039(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5987(5)
_cell_length_b                   15.0870(9)
_cell_length_c                   11.7651(7)
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      2.55
_cell_volume                     1672.25(17)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            50871
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         26.390
_diffrn_reflns_theta_min         2.549
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_refine_diff_density_max         1.426
_refine_diff_density_min         -1.122
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3404
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1206
_refine_ls_R_factor_gt           0.0878
_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^)+(0.1343P)^2^+4.5551P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2208
_refine_ls_wR_factor_ref         0.2716
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2564
_reflns_number_total             3404
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04892c2.cif
_cod_data_source_block           155_a_pl
_cod_depositor_comments
'Adding full bibliography for 7135100--7135101.cif.'
_cod_database_code               7135101
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C21-H21
 0.92 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7)
;
_shelx_res_checksum              10593
_shelx_hkl_checksum              20472
_olex2_submission_special_instructions 'No special instructions were received'