Development of an Enantioselective Route toward the Lycopodium Alkaloids: Total Synthesis of Lycopodine
Hua Yang; Rich G. Carter; Journal of Organic Chemistry 75 (2010) 4929–4938; doi:10.1021/jo100916x

data_4025560
_publ_section_title
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 Development of an Enantioselective Route toward the Lycopodium Alkaloids:
 Total Synthesis of Lycopodine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4929
_journal_page_last               4938
_journal_paper_doi               10.1021/jo100916x
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C18 H23 N3 O4 S'
_chemical_formula_weight         377.45
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXLTL
_cell_angle_alpha                90.00
_cell_angle_beta                 115.123(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.360(5)
_cell_length_b                   8.016(3)
_cell_length_c                   16.894(6)
_cell_measurement_reflns_used    3000
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.17
_cell_measurement_theta_min      2.65
_cell_volume                     1883.3(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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0666
_diffrn_reflns_av_sigmaI/netI    0.0943
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15736
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.33
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.9960
_exptl_absorpt_correction_T_min  0.9333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            collorless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.759
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         6626
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0685
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0926P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1541
_refine_ls_wR_factor_ref         0.1678
_reflns_number_gt                5086
_reflns_number_total             6626
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100916x_si_005.cif
_cod_data_source_block           rc25
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        1883.2(11)
_cod_database_code               4025560