Donor-acceptor 1,2,4,5-Tetrazines Prepared by Buchwald-Hartwig Cross-Coupling Reaction and Their Photoluminescence Turn-on Property by Inverse Electron Demand Diels-Alder Reaction.
Qu, Yangyang; Pander, Piotr Henryk; Vybornyi, Oleh; Vasylieva, Marharyta; Guillot, Régis; Miomandre, Fabien; Dias, Fernando B.; Skabara, Peter J.; Data, Przemyslaw; Clavier, Gilles; Audebert, Pierre; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b02817

data_4037914
_publ_section_title
;
 Donor-acceptor 1,2,4,5-Tetrazines Prepared by Buchwald-Hartwig
 Cross-Coupling Reaction and Their Photoluminescence Turn-on Property by
 Inverse Electron Demand Diels-Alder Reaction.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02817
_journal_year                    2020
_chemical_formula_moiety         'C28 H25 N3 S'
_chemical_formula_sum            'C28 H25 N3 S'
_chemical_formula_weight         435.57
_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   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 116.616(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.502(5)
_cell_length_b                   11.158(4)
_cell_length_c                   15.629(6)
_cell_measurement_reflns_used    9857
_cell_measurement_temperature    250(1)
_cell_measurement_theta_max      22.54
_cell_measurement_theta_min      2.34
_cell_volume                     2261.0(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      250(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.4509
_diffrn_reflns_av_unetI/netI     0.2082
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            158600
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.840
_diffrn_reflns_theta_min         2.336
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.9461
_exptl_absorpt_correction_T_min  0.9141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'apex3 Bruker'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       plate
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.897
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         7032
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.897
_refine_ls_R_factor_all          0.1904
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0495P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1180
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2732
_reflns_number_total             7032
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02817_si_002.cif
_cod_data_source_block           DA3
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4037914
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.998
_shelx_res_checksum              29637
_shelx_hkl_checksum              67804