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_4037912
_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 O'
_chemical_formula_sum            'C28 H25 N3 O'
_chemical_formula_weight         419.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 102.525(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.091(9)
_cell_length_b                   8.713(3)
_cell_length_c                   17.546(6)
_cell_measurement_reflns_used    9686
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      30.73
_cell_measurement_theta_min      2.44
_cell_volume                     4342(3)
_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      100(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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  0.1216
_diffrn_reflns_av_unetI/netI     0.0683
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            78219
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         31.044
_diffrn_reflns_theta_min         2.378
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9462
_exptl_absorpt_correction_T_min  0.9142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'apex3 Bruker'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       block
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         6909
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.0588
_refine_ls_shift/su_max          0.082
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0550P)^2^+2.1793P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1305
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4353
_reflns_number_total             6909
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02817_si_001.cif
_cod_data_source_block           DA2
_cod_original_cell_volume        4342(2)
_cod_original_sg_symbol_Hall     '-C 2yn'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4037912
_shelx_estimated_absorpt_t_min   0.991
_shelx_estimated_absorpt_t_max   0.994
_shelx_res_checksum              4187
_shelx_hkl_checksum              16965