Lewis Acid-Promoted Three-Component Reactions of Propargylic Alcohols with 2-Butynedioates and Secondary Amines
Guangwei Yin; Yuanxun Zhu; Ping Lu; Yanguang Wang; Journal of Organic Chemistry 76 (2011) 8922–8929; doi:10.1021/jo2016407

data_4026711
_publ_section_title
;
 Lewis Acid-Promoted Three-Component Reactions of Propargylic Alcohols
 with 2-Butynedioates and Secondary Amines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8922
_journal_page_last               8929
_journal_paper_doi               10.1021/jo2016407
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C33 H35 N O4'
_chemical_formula_sum            'C33 H35 N O4'
_chemical_formula_weight         509.62
_space_group_IT_number           14
_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                 98.895(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.0989(8)
_cell_length_b                   8.7981(6)
_cell_length_c                   19.2978(9)
_cell_measurement_reflns_used    3990
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5300
_cell_measurement_theta_min      2.7789
_cell_volume                     2868.2(3)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w 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  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11558
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.34
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9825
_exptl_absorpt_correction_T_min  0.9758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Oxford Diffraction, 2010) 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         5252
_refine_ls_number_restraints     886
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0468
_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^)+(0.0456P)^2^+0.6990P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1195
_reflns_number_gt                3711
_reflns_number_total             5252
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2016407_si_002.cif
_cod_data_source_block           110309_ygw571_109
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4026711