Toward a unified approach for the lycopodines: synthesis of 10-hydroxylycopodine, deacetylpaniculine, and paniculine.
Saha, Mrinmoy; Carter, Rich G.; Organic letters 15 (2013) 736–739; doi:10.1021/ol303272w

data_1508925
_publ_section_title
;
 Toward a unified approach for the lycopodines: synthesis of
 10-hydroxylycopodine, deacetylpaniculine, and paniculine.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              736
_journal_page_last               739
_journal_paper_doi               10.1021/ol303272w
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C22 H30 O6 S'
_chemical_formula_weight         422.52
_space_group_IT_number           19
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_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXLTL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4382(13)
_cell_length_b                   10.6416(17)
_cell_length_c                   23.583(4)
_cell_measurement_reflns_used    9655
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.91
_cell_measurement_theta_min      2.56
_cell_volume                     2117.7(6)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Apex 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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_max       10
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_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            23853
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.9777
_exptl_absorpt_correction_T_min  0.9301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         4622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0288
_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^)+(0.0448P)^2^+0.2367P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0732
_reflns_number_gt                4455
_reflns_number_total             4622
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol303272w_si_003.cif
_cod_data_source_block           rc61
_cod_depositor_comments
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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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1508925