Synthetic Studies on Dicyclopenta[a,d]cyclooctane Terpenoids: Construction of the Core Structure of Fusicoccins and Ophiobolins on the Route Involving a Wagner-Meerwein Rearrangement
Michał Michalak; Karol Michalak; Zofia Urbanczyk-Lipkowska; Jerzy Wicha; Journal of Organic Chemistry 76 (2011) 7497–7509; doi:10.1021/jo201357p

data_4026588
_publ_section_title
;
 Synthetic Studies on Dicyclopenta[a,d]cyclooctane Terpenoids:
 Construction of the Core Structure of Fusicoccins and Ophiobolins on the
 Route Involving a Wagner-Meerwein Rearrangement
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7497
_journal_page_last               7509
_journal_paper_doi               10.1021/jo201357p
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C21 H30 O3'
_chemical_formula_weight         330.45
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 90.73(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.607(3)
_cell_length_b                   5.1750(10)
_cell_length_c                   21.855(4)
_cell_measurement_reflns_used    5
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.07
_cell_measurement_theta_min      18.82
_cell_volume                     1878.1(6)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_sigmaI/netI    0.2041
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            2484
_diffrn_reflns_theta_full        57.23
_diffrn_reflns_theta_max         57.23
_diffrn_reflns_theta_min         3.32
_diffrn_standards_decay_%        3
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  3600
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.601
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.2426
_refine_ls_R_factor_gt           0.0656
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0675P)^2^+0.7289P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1883
_reflns_number_gt                984
_reflns_number_total             2413
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201357p_si_002.cif
_cod_data_source_block           mm625_3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
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_cod_database_code               4026588