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_4101279
_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            'C23 H28 N2 O4'
_chemical_formula_weight         396.47
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1539(15)
_cell_length_b                   11.5677(17)
_cell_length_c                   17.553(3)
_cell_measurement_reflns_used    5830
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.5
_cell_volume                     2061.8(5)
_computing_cell_refinement       'Bruker SAINT+'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15291
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.11
_diffrn_standards_decay_%        <1%
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9870
_exptl_absorpt_correction_T_min  0.9751
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1999)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Blocks
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3619
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.926
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          0.036
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.5000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1381
_refine_ls_wR_factor_ref         0.1436
_reflns_number_gt                3254
_reflns_number_total             3619
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja061256trom20060221_080322.cif
_cod_data_source_block           hayb
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' 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      P2(1)2(1)2(1)
_cod_database_code               4101279