Phosphine catalysed (5 + 1) annulation of ynone/cinnamates with primary amines
Ametovski, Jhi; Dutta, Uttam; Burchill, Laura; Maiti, Debrabrata; Lupton, David William; Hooper, Joel; Chemical Communications  (2017) –; doi:10.1039/C7CC08252E

data_7120866
_publ_section_title
;
 Phosphine catalysed (5 + 1) annulation of ynone/cinnamates with primary
 amines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C7CC08252E
_journal_year                    2017
_chemical_formula_moiety         'C27 H25 N O5 S'
_chemical_formula_sum            'C27 H25 N O5 S'
_chemical_formula_weight         475.54
_chemical_melting_point          391
_chemical_name_systematic
'ethyl (Z)-2-(3-benzylidene-4-oxo-2-tosyl-1,2,3,4-tetrahydroisoquinolin-1-yl)acetate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-10-16 deposited with the CCDC.
2017-11-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.143(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6859(10)
_cell_length_b                   13.7251(15)
_cell_length_c                   15.4139(13)
_cell_measurement_reflns_used    2505
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.92
_cell_measurement_theta_min      2.26
_cell_volume                     2257.3(4)
_computing_cell_refinement       'Bruker Apex2 v2014.7-1 (Bruker AXS, 2014)'
_computing_data_collection       'Bruker Apex2 v2014.7-1 (Bruker AXS, 2014)'
_computing_data_reduction        'Bruker Apex2 v2014.7-1 (Bruker AXS, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14049
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.382
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/3 (Bruker AXS, 2014)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       prism
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0428
_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^)+(0.0462P)^2^+0.6382P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1116
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4067
_reflns_number_total             5396
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc08252e2.cif
_cod_data_source_block           shelx
_cod_database_code               7120866
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              8973