Photo-induced C–H bond activation of N,N′-dialkylethylenediamine upon aza-Michael addition to 1,8-pyrenedione: facile synthesis of fluorescent pyrene derivatives
Yao, Wei; Sun, Mingtai; Zhang, Yuannian; Yang, Hui; Liang, Dong; Wu, Haixia; Ni, Runyan; Wong, Ming Wah; Huang, Dejian; Organic Chemistry Frontiers 5 (2018) 1679–; doi:10.1039/C8QO00183A

data_1554281
_publ_section_title
;
 Photo-induced C--H bond activation of N,N&#x2032;-dialkylethylenediamine
 upon aza-Michael addition to 1,8-pyrenedione: facile synthesis of
 fluorescent pyrene derivatives
;
_journal_issue                   10
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1679
_journal_paper_doi               10.1039/C8QO00183A
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C9 H6 N O'
_chemical_formula_sum            'C9 H6 N O'
_chemical_formula_weight         144.15
_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   mixed
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2016-09-02 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.9420(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.3145(4)
_cell_length_b                   13.4792(4)
_cell_length_c                   7.0709(2)
_cell_measurement_reflns_used    3289
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.530
_cell_measurement_theta_min      6.568
_cell_volume                     1266.00(6)
_computing_cell_refinement
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_collection       'APEX v2014.11.0'
_computing_data_reduction        'Saint, APEX v2014.11.0.'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX v2014.11.0.'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT, Acta Cryst., Sect. A 2015, A71, 3-8.'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from \q/2\q scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6746
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.530
_diffrn_reflns_theta_min         6.568
_exptl_absorpt_coefficient_mu    0.815
_exptl_absorpt_correction_T_max  0.922
_exptl_absorpt_correction_T_min  0.825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.101
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         1293
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0718P)^2^+0.4279P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1143
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1170
_reflns_number_total             1293
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00183a2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1554281
_shelx_estimated_absorpt_t_min   0.825
_shelx_estimated_absorpt_t_max   0.922
_shelxl_version_number           2014/6
_shelx_res_checksum              47437
_shelx_hkl_checksum              5398