Synthesis of atrans,syn,trans-Dodecahydrophenanthrene via a Bicyclic Transannular Diels-Alder Reaction: Intermediate for the Synthesis of Fusidic Acid
Michael E. Jung; Ting-Hu Zhang; Rebecca M. Lui; Osvaldo Gutierrez; K. N. Houk; Journal of Organic Chemistry 75 (2010) 6933–6940; doi:10.1021/jo101533h

data_4025739
_publ_section_title
;
 Synthesis of atrans,syn,trans-Dodecahydrophenanthrene via a Bicyclic
 Transannular Diels-Alder Reaction: Intermediate for the Synthesis of
 Fusidic Acid
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6933
_journal_page_last               6940
_journal_paper_doi               10.1021/jo101533h
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C16 H24 O'
_chemical_formula_sum            'C16 H24 O'
_chemical_formula_weight         232.35
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.049(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.481(2)
_cell_length_b                   6.5941(8)
_cell_length_c                   12.4508(16)
_cell_measurement_reflns_used    3174
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      3.74
_cell_volume                     1271.0(3)
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(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  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15425
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         3.74
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9964
_exptl_absorpt_correction_T_min  0.9568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Bruker)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0499P)^2^+0.3857P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1079
_reflns_number_gt                2490
_reflns_number_total             3149
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101533h_si_002.cif
_cod_data_source_block           jung509s
_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        1271.1(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4025739