Phosphine-catalyzed one-pot isomerization of 3-alkynoates and [2 + 3]-cycloaddition with imines: formal synthesis of Securinega alkaloid (±)-allosecurinine
Sampath, Magesh; Lee, Pei-Ying Beatrix; Loh, Teck-Peng; Chemical Science 2 (2011) 1988–; doi:10.1039/c1sc00311a

data_1515498
_publ_section_title
;
 Phosphine-catalyzed one-pot isomerization of 3-alkynoates and [2 +
 3]-cycloaddition with imines: formal synthesis of Securinega alkaloid
 (+-)-allosecurinine
;
_journal_issue                   10
_journal_name_full               'Chemical Science'
_journal_page_first              1988
_journal_paper_doi               10.1039/c1sc00311a
_journal_volume                  2
_journal_year                    2011
_chemical_formula_moiety         'C21 H31 I2 N O4 S'
_chemical_formula_sum            'C21 H31 I2 N O4 S'
_chemical_formula_weight         647.33
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 114.7990(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   29.1152(8)
_cell_length_b                   11.5743(3)
_cell_length_c                   15.8437(4)
_cell_measurement_reflns_used    9849
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      34.24
_cell_measurement_theta_min      2.57
_cell_volume                     4846.8(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \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  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            36521
_diffrn_reflns_theta_full        34.27
_diffrn_reflns_theta_max         34.27
_diffrn_reflns_theta_min         2.78
_exptl_absorpt_coefficient_mu    2.707
_exptl_absorpt_correction_T_max  0.6135
_exptl_absorpt_correction_T_min  0.4106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2544
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.854
_refine_diff_density_min         -1.237
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         10020
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0289P)^2^+11.9264P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0798
_reflns_number_gt                7989
_reflns_number_total             10020
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1sc00311a.txt
_cod_data_source_block           ltp184s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1515498