Assembly of Four Diverse Heterocyclic Libraries Enabled by Prins Cyclization, Au-Catalyzed Enyne Cycloisomerization, and Automated Amide Synthesis
Jiayue Cui; David I. Chai; Christopher Miller; Jason Hao; Christopher Thomas; JingQi Wang; Karl A. Scheidt; Sergey A. Kozmin; Journal of Organic Chemistry 77 (2012) 7435–7470; doi:10.1021/jo301061r

data_4027445
_publ_section_title
;
 Assembly of Four Diverse Heterocyclic Libraries Enabled by Prins
 Cyclization, Au-Catalyzed Enyne Cycloisomerization, and Automated Amide
 Synthesis
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7435
_journal_page_last               7470
_journal_paper_doi               10.1021/jo301061r
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C16 H21 N O5'
_chemical_formula_weight         307.34
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_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.114(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.503(3)
_cell_length_b                   12.281(3)
_cell_length_c                   11.173(3)
_cell_measurement_temperature    100(2)
_cell_volume                     1418.8(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.1416
_diffrn_reflns_av_sigmaI/netI    0.1489
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13483
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_correction_T_min  0.9707
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.745
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2528
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.745
_refine_ls_R_factor_all          0.1140
_refine_ls_R_factor_gt           0.0568
_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^)+(0.0281P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.1034
_reflns_number_gt                1222
_reflns_number_total             2528
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301061r_si_004.cif
_cod_data_source_block           chai03s
_cod_original_cell_volume        1418.8(6)
_cod_database_code               4027445