One pot cascade synthesis of fused heterocycles from furan-tethered terminal alkynes and aldehydes in the presence of amines and CuBr
Zhang, Yan-Yan; Hao, Jian; Shi, Min; Organic Chemistry Frontiers 2 (2015) 394–; doi:10.1039/C5QO00033E

data_1553103
_publ_section_title
;
 One pot cascade synthesis of fused heterocycles from furan-tethered
 terminal alkynes and aldehydes in the presence of amines and CuBr
;
_journal_issue                   4
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              394
_journal_paper_doi               10.1039/C5QO00033E
_journal_volume                  2
_journal_year                    2015
_chemical_formula_sum            'C16 H22 N O3 S'
_chemical_formula_weight         308.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-04-02 deposited with the CCDC.
2015-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                104.782(4)
_cell_angle_beta                 101.238(4)
_cell_angle_gamma                100.235(4)
_cell_formula_units_Z            2
_cell_length_a                   6.2097(13)
_cell_length_b                   11.272(2)
_cell_length_c                   11.547(3)
_cell_measurement_reflns_used    2252
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      56.248
_cell_measurement_theta_min      6.145
_cell_volume                     744.1(3)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4414
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         1.885
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             330
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       0.124(16)
_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   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2882
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0656
_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^)+(0.1221P)^2^+0.0825P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1786
_refine_ls_wR_factor_ref         0.1866
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2469
_reflns_number_total             2882
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5qo00033e2.cif
_cod_data_source_block           cd214171
_cod_original_cell_volume        744.2(3)
_cod_database_code               1553103
_shelxl_version_number           2013-4
_shelx_res_checksum              78411
_shelx_hkl_checksum              88057