Collective total synthesis of tetracyclic diquinane lycopodium alkaloids (+)-paniculatine, (-)-magellanine, (+)-magellaninone and analogues thereof.
Jiang, Shi-Zhi; Lei, Ting; Wei, Kun; Yang, Yu-Rong; Organic letters 16 (2014) 5612–5615; doi:10.1021/ol502679v

data_1517978
_publ_section_title
;
 Collective total synthesis of tetracyclic diquinane lycopodium alkaloids
 (+)-paniculatine, (-)-magellanine, (+)-magellaninone and analogues
 thereof.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5612
_journal_page_last               5615
_journal_paper_doi               10.1021/ol502679v
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H31 N O4 S'
_chemical_formula_sum            'C23 H31 N O4 S'
_chemical_formula_weight         417.55
_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                   6.6647(7)
_cell_length_b                   8.0882(8)
_cell_length_c                   40.025(4)
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.88
_cell_measurement_theta_min      2.72
_cell_volume                     2157.6(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_number            22755
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         1.02
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.9893
_exptl_absorpt_correction_T_min  0.8804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.73
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         6101
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0374P)^2^+0.7284P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0891
_reflns_number_gt                5779
_reflns_number_total             6101
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502679v_si_002.cif
_cod_data_source_block           mo_ajsz1_0m
_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/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 1517976--1517978.cif.
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_cod_database_code               1517978