Synthetic Studies on Schisandra nortriterpenoids. Stereocontrolled Synthesis of Enantiopure C-5-epiABC Ring Systems of Micrandilactone A and Lancifodilactone G Using RCM
Soumitra Maity; Kiran Matcha; Subrata Ghosh; Journal of Organic Chemistry 75 (2010) 4192–4200; doi:10.1021/jo1006448

data_4025497
_publ_section_title
;
 Synthetic Studies on Schisandra nortriterpenoids. Stereocontrolled
 Synthesis of Enantiopure C-5-epiABC Ring Systems of Micrandilactone A and
 Lancifodilactone G Using RCM
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4192
_journal_page_last               4200
_journal_paper_doi               10.1021/jo1006448
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C20 H20 Br O3'
_chemical_formula_weight         388.27
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_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                 106.099(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.250(3)
_cell_length_b                   5.7487(10)
_cell_length_c                   18.732(3)
_cell_measurement_temperature    150(2)
_cell_volume                     1888.2(5)
_computing_cell_refinement       'BRUKER APEX II'
_computing_data_collection       'BRUKER APEX II'
_computing_data_reduction        'BRUKER APEX II'
_computing_molecular_graphics    'MERCURY 2.3, PLATON-97, ORTEP3V2'
_computing_publication_material  'MERCURY 2.3, PLATON-97, ORTEP3V2'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 3
_diffrn_measured_fraction_theta_full 0.919
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device_type  'BRUKER CCD AREA DETECTOR'
_diffrn_measurement_method       'OMEGA SCAN'
_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  0.0768
_diffrn_reflns_av_sigmaI/netI    0.0773
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10469
_diffrn_reflns_theta_full        30.32
_diffrn_reflns_theta_max         30.32
_diffrn_reflns_theta_min         1.13
_exptl_absorpt_coefficient_mu    2.190
_exptl_absorpt_correction_T_max  0.7638
_exptl_absorpt_correction_T_min  0.7347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             796
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.782
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2851
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0601
_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^)+(0.0974P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1566
_refine_ls_wR_factor_ref         0.1691
_reflns_number_gt                1892
_reflns_number_total             2851
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1006448_si_004.cif
_cod_data_source_block           sm01_0m
_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.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' 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        1888.2(6)
_cod_database_code               4025497