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_7155830
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4726(6)
_cell_length_b                   20.1154(16)
_cell_length_c                   23.4601(19)
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      64.30
_cell_measurement_theta_min      2.89
_cell_volume                     3526.4(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  PLATON
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0941
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            35935
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        65.090
_diffrn_reflns_theta_max         65.090
_diffrn_reflns_theta_min         2.894
_exptl_absorpt_coefficient_mu    1.098
_exptl_absorpt_correction_T_max  0.6712
_exptl_absorpt_correction_T_min  0.5325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.008
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.051
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
; 
 Flack x determined using 1468 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.034(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         5895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0701
_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^)+(0.1334P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1881
_refine_ls_wR_factor_ref         0.2039
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                4415
_reflns_number_total             5895
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01665d2.cif
_cod_data_source_block           ar160769_1_0m
_cod_database_code               7155830
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.765
_shelx_estimated_absorpt_t_max   0.946
_shelx_res_checksum              68322