Synthesis of the Octahydronaphthalene Core of Nahuoic Acid A via a B(C6F5)3-Catalyzed Intramolecular Diels-Alder (IMDA) Reaction
Guillade, Lucía; Gónzalez Pérez, Adán B; R. de LERA, Angel; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01665D

data_7155831
_publ_section_title
;
 Synthesis of the Octahydronaphthalene Core of Nahuoic Acid A via a
 B(C6F5)3-Catalyzed Intramolecular Diels-Alder (IMDA) Reaction
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01665D
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C31 H58 O3 Si2'
_chemical_formula_weight         534.95
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-05-02 deposited with the CCDC.
2017-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.347(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.2887(11)
_cell_length_b                   17.918(4)
_cell_length_c                   12.294(2)
_cell_measurement_reflns_used    1453
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      43.95
_cell_measurement_theta_min      3.71
_cell_volume                     1768.9(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    PLATON
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker CCD Smart 6000'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Incoatec QuazarTM MX multilayer optics'
_diffrn_radiation_source         'Incoatec I\muS microsource'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            45058
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        65.082
_diffrn_reflns_theta_max         65.082
_diffrn_reflns_theta_min         3.711
_exptl_absorpt_coefficient_mu    1.094
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.004
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.216
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details
; 
 Classical Flack method preferred over Parsons because s.u. lower. 
;
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5959
_refine_ls_number_restraints     106
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0969
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2401
_refine_ls_wR_factor_ref         0.2533
_reflns_Friedel_coverage         0.925
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                5054
_reflns_number_total             5959
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01665d2.cif
_cod_data_source_block           ar160909_1_0m_a
_cod_original_cell_volume        1769.0(5)
_cod_database_code               7155831
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.798
_shelx_estimated_absorpt_t_max   0.930
_shelx_res_checksum              47090