Total synthesis of (-)- and ent-(+)-vindoline and related alkaloids.
Ishikawa, Hayato; Elliott, Gregory I; Velcicky, Juraj; Choi, Younggi; Boger, Dale L; Journal of the American Chemical Society 128 (2006) 10596–10612; doi:10.1021/ja061256t

data_4101283
_publ_section_title
;
 Total synthesis of (-)- and ent-(+)-vindoline and related alkaloids.
;
_journal_issue                   32
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10596
_journal_page_last               10612
_journal_paper_doi               10.1021/ja061256t
_journal_volume                  128
_journal_year                    2006
_chemical_formula_sum            'C37 H37 Br N2 O8'
_chemical_formula_weight         717.60
_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                109.94(3)
_cell_angle_beta                 95.96(3)
_cell_angle_gamma                110.80(3)
_cell_formula_units_Z            4
_cell_length_a                   14.772(3)
_cell_length_b                   14.944(3)
_cell_length_c                   18.334(4)
_cell_measurement_reflns_used    4824
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.42
_cell_measurement_theta_min      2.23
_cell_volume                     3438.0(12)
_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, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_sigmaI/netI    0.0894
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25291
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.22
_diffrn_standards_decay_%        1
_exptl_absorpt_coefficient_mu    1.250
_exptl_absorpt_correction_T_max  0.8062
_exptl_absorpt_correction_T_min  0.7209
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1999)'
_exptl_crystal_colour            Colorless'
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.759
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     873
_refine_ls_number_reflns         12045
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.960
_refine_ls_R_factor_all          0.1431
_refine_ls_R_factor_gt           0.0633
_refine_ls_shift/su_max          0.253
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0860P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1423
_refine_ls_wR_factor_ref         0.1804
_reflns_number_gt                5759
_reflns_number_total             12045
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja061256trom20060221_080430.cif
_cod_data_source_block           yoch
_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               4101283