Diastereoselective Synthesis of Complex cis-Hexahydroindanes by Reductive Alkylation
Hilan Z. Kaplan; Victor L. Rendina; Jason S. Kingsbury; Journal of Organic Chemistry 78 (2013) 4620–4626; doi:10.1021/jo400670y

data_4028216
_publ_section_title
;
 Diastereoselective Synthesis of Complex cis-Hexahydroindanes by Reductive
 Alkylation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4620
_journal_page_last               4626
_journal_paper_doi               10.1021/jo400670y
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C18 H24 O2'
_chemical_formula_sum            'C18 H24 O2'
_chemical_formula_weight         272.37
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                87.925(2)
_cell_angle_beta                 77.109(2)
_cell_angle_gamma                80.284(2)
_cell_formula_units_Z            2
_cell_length_a                   8.1744(14)
_cell_length_b                   8.2642(14)
_cell_length_c                   11.2317(19)
_cell_measurement_reflns_used    4865
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.50
_cell_volume                     729.0(2)
_computing_cell_refinement       'Bruker SAINT'
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '0.3 deg wide \w exposures'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8363
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9937
_exptl_absorpt_correction_T_min  0.9875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       na
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3168
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0459
_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^)+(0.0639P)^2^+0.2848P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1199
_reflns_number_gt                2735
_reflns_number_total             3168
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400670y_si_002.cif
_cod_data_source_block           C18H24O2
_cod_database_code               4028216