Enantioselective total synthesis of (+)- and (-)-nigellamine A2.
Bian, Jianwei; Van Wingerden, Matthew; Ready, Joseph M; Journal of the American Chemical Society 128 (2006) 7428–7429; doi:10.1021/ja061559n

data_4101505
_publ_section_title
;
 Enantioselective total synthesis of (+)- and (-)-nigellamine A2.
;
_journal_issue                   23
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7428
_journal_page_last               7429
_journal_paper_doi               10.1021/ja061559n
_journal_volume                  128
_journal_year                    2006
_chemical_formula_sum            'C15 H15 I O3'
_chemical_formula_weight         370.000
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           145
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_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                 90.000(3)
_cell_angle_gamma                120.00
_cell_formula_units_Z            3
_cell_length_a                   15.831(7)
_cell_length_b                   15.831(4)
_cell_length_c                   5.7920(14)
_cell_measurement_reflns_used    45
_cell_measurement_temperature    293(2)
_cell_volume                     1257.1(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Kappa CCD'
_diffrn_measurement_method       Collect
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1519
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       1
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            837
_diffrn_reflns_theta_full        20.74
_diffrn_reflns_theta_max         20.74
_diffrn_reflns_theta_min         4.36
_exptl_absorpt_coefficient_mu    1.910
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       needle
_exptl_crystal_F_000             546
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(9)
_refine_ls_extinction_coef       0.00(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.654
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         837
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.654
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0615
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1583
_refine_ls_wR_factor_ref         0.1690
_reflns_number_gt                603
_reflns_number_total             837
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja061559nsi20060517_051336.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal' 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      P3(2)
_cod_original_formula_sum        'C15 H15 I1    O3'
_cod_database_code               4101505