Total synthesis of (±)-hirsutine: application of phosphine-catalyzed imine-allene [4 + 2] annulation.
Villa, Reymundo A.; Xu, Qihai; Kwon, Ohyun; Organic letters 14 (2012) 4634–4637; doi:10.1021/ol302077n

data_1508630
_publ_section_title
;
 Total synthesis of (+-)-hirsutine: application of phosphine-catalyzed
 imine-allene [4 + 2] annulation.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4634
_journal_page_last               4637
_journal_paper_doi               10.1021/ol302077n
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         '2(C21 H24 N2 O5), C H2 Cl2'
_chemical_formula_sum            'C43 H50 Cl2 N4 O10'
_chemical_formula_weight         853.77
_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                 100.2810(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   28.956(3)
_cell_length_b                   12.8042(11)
_cell_length_c                   11.6536(10)
_cell_measurement_reflns_used    9596
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.95
_cell_measurement_theta_min      3.91
_cell_volume                     4251.3(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0167
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20317
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.97
_diffrn_reflns_theta_min         3.84
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Bruker)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1800
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         6073
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0603P)^2^+3.7405P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1226
_reflns_number_gt                5096
_reflns_number_total             6073
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302077n_si_003.cif
_cod_data_source_block           kw1208s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1508630