Bioorthogonal fluorogenic chemistry using a light-activated tetrazine.
Gilmer, Selena C. L.; Vernall, Andrea J.; Organic & biomolecular chemistry 23 (2025) 9361–9367; doi:10.1039/d5ob01476j

data_7160778
_publ_section_title
;
 Bioorthogonal fluorogenic chemistry using a light-activated tetrazine.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9361
_journal_page_last               9367
_journal_paper_doi               10.1039/d5ob01476j
_journal_volume                  23
_journal_year                    2025
_chemical_formula_sum            'C22 H18 N4 O2 S'
_chemical_formula_weight         402.46
_chemical_properties_physical    Moisture-sensitive
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-08-20 deposited with the CCDC.	2025-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.899(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.4895(5)
_cell_length_b                   9.9097(2)
_cell_length_c                   9.9731(3)
_cell_measurement_reflns_used    9245
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.0840
_cell_measurement_theta_min      4.4750
_cell_volume                     1925.92(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.1725
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13785
_diffrn_reflns_point_group_measured_fraction_full 0.906
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.662
_diffrn_reflns_theta_min         4.538
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.715
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_recrystallization_method 'Slow evaporation'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details
;
 Flack x determined using 1385 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3407
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0661
_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^)+(0.1236P)^2^+4.0356P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1851
_refine_ls_wR_factor_ref         0.1860
_reflns_Friedel_coverage         0.787
_reflns_Friedel_fraction_full    0.813
_reflns_Friedel_fraction_max     0.782
_reflns_number_gt                3347
_reflns_number_total             3407
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01476j2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7160778.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7160778
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              55807