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_4025561
_publ_section_title
;
 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 N O3 S'
_chemical_formula_weight         333.43
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 98.059(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.254(3)
_cell_length_b                   7.650(3)
_cell_length_c                   25.887(9)
_cell_measurement_reflns_used    3366
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.49
_cell_volume                     1618.4(10)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            17815
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_correction_T_min  0.9562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         3708
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0455
_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^)+(0.0595P)^2^+0.4882P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1189
_reflns_number_gt                2972
_reflns_number_total             3708
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100916x_si_006.cif
_cod_data_source_block           rc20
_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        1618.5(10)
_cod_database_code               4025561