Design of a Coumarin-Based Triketone as a Fluorescent Protecting Group for Primary Amines
Pei-Yu Kuo; Ding-Yah Yang; Journal of Organic Chemistry 73 (2008) 6455–6458; doi:10.1021/jo801060p

data_4023624
_publ_section_title
;
 Design of a Coumarin-Based Triketone as a Fluorescent
 Protecting Group for Primary Amines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6455
_journal_page_last               6458
_journal_paper_doi               10.1021/jo801060p
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C13 H13 N3 O2'
_chemical_formula_sum            'C13 H13 N3 O2'
_chemical_formula_weight         243.26
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                81.256(2)
_cell_angle_beta                 79.215(2)
_cell_angle_gamma                62.150(2)
_cell_formula_units_Z            2
_cell_length_a                   7.2347(8)
_cell_length_b                   7.4914(9)
_cell_length_c                   12.4921(14)
_cell_measurement_reflns_used    2296
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.979
_cell_measurement_theta_min      3.079
_cell_volume                     586.42(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3317
_diffrn_reflns_theta_full        26.03
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         3.08
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.139
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelpiped
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.76
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.021(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.256
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2271
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.256
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0635
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1500P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2033
_refine_ls_wR_factor_ref         0.2142
_reflns_number_gt                1955
_reflns_number_total             2271
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801060p-file006.cif
_cod_data_source_block           yut40m
_cod_database_code               4023624