Catalytic Coupling of Arene C-H Bonds and Alkynes for the Synthesis of Coumarins: Substrate Scope and Application to the Development of Neuroimaging Agents
Paul A. Vadola; Dalibor Sames; Journal of Organic Chemistry 77 (2012) 7804–7814; doi:10.1021/jo3006842

data_4027477
_publ_section_title
;
 Catalytic Coupling of Arene C-H Bonds and Alkynes for the Synthesis of
 Coumarins: Substrate Scope and Application to the Development of
 Neuroimaging Agents
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7804
_journal_page_last               7814
_journal_paper_doi               10.1021/jo3006842
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C30 H30 N2 O4'
_chemical_formula_weight         482.56
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_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.8320(10)
_cell_angle_beta                 90.81
_cell_angle_gamma                93.4290(10)
_cell_formula_units_Z            2
_cell_length_a                   9.4174(4)
_cell_length_b                   10.2417(4)
_cell_length_c                   13.5578(4)
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      32.50
_cell_measurement_theta_min      2.20
_cell_volume                     1241.88(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      125(2)
_diffrn_measured_fraction_theta_full 0.930
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21718
_diffrn_reflns_theta_full        32.69
_diffrn_reflns_theta_max         32.69
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9915
_exptl_absorpt_correction_T_min  0.9830
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         8503
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0719P)^2^+0.1888P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1341
_reflns_number_gt                6403
_reflns_number_total             8503
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3006842_si_003.cif
_cod_data_source_block           pvs10
_cod_database_code               4027477