Application of Cross-Conjugated Heteroaromatic Betaines to the Synthesis of the Schizozygane Alkaloid (\±)-Strempeliopine
Drew R. Bobeck; Hyoung Ik Lee; Andrew C. Flick; Albert Padwa; Journal of Organic Chemistry 74 (2009) 7389–7402; doi:10.1021/jo901336z

data_4024874
_publ_section_title
;
Application of Cross-Conjugated Heteroaromatic Betaines to the Synthesis of
the Schizozygane Alkaloid (\+-)-Strempeliopine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7389
_journal_page_last               7402
_journal_paper_doi               10.1021/jo901336z
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C21 H25.93 Br0.07 N2 O3'
_chemical_formula_sum            'C21 H25.93 Br0.07 N2 O3'
_chemical_formula_weight         359.57
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                75.684(7)
_cell_angle_beta                 75.833(6)
_cell_angle_gamma                87.738(6)
_cell_formula_units_Z            2
_cell_length_a                   8.0200(8)
_cell_length_b                   10.4318(12)
_cell_length_c                   11.5980(15)
_cell_measurement_reflns_used    900
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      63.00
_cell_measurement_theta_min      8.73
_cell_volume                     911.37(18)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.675
_diffrn_measured_fraction_theta_max 0.675
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3966
_diffrn_reflns_theta_full        65.76
_diffrn_reflns_theta_max         65.76
_diffrn_reflns_theta_min         8.73
_exptl_absorpt_coefficient_mu    0.862
_exptl_absorpt_correction_T_max  0.9469
_exptl_absorpt_correction_T_min  0.8069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         2131
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0893
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1700P)^2^+1.9000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2834
_refine_ls_wR_factor_ref         0.2911
_reflns_number_gt                1735
_reflns_number_total             2131
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901336z_si_002.cif
_cod_data_source_block           drb3_135s
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4024874