Diastereoselective Friedel-Crafts Alkylation of Hydronaphthalenes
Jennifer Tsoung; Katja Krämer; Adam Zajdlik; Clemence Liébert; Mark Lautens; Journal of Organic Chemistry 76 (2011) 9031–9045; doi:10.1021/jo201781x

data_4026725
_publ_section_title
;
 Diastereoselective Friedel-Crafts Alkylation of Hydronaphthalenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9031
_journal_page_last               9045
_journal_paper_doi               10.1021/jo201781x
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C22 H17'
_chemical_formula_weight         281.36
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 107.995(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.0800(5)
_cell_length_b                   7.0463(3)
_cell_length_c                   11.1384(6)
_cell_measurement_reflns_used    3113
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.71
_cell_measurement_theta_min      3.28
_cell_volume                     752.42(6)
_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      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6609
_diffrn_reflns_theta_full        26.91
_diffrn_reflns_theta_max         26.91
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_correction_T_min  0.9861
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_meas      0
_exptl_crystal_description       block
_exptl_crystal_F_000             298
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         1756
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0491P)^2^+0.0707P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0917
_reflns_number_gt                1522
_reflns_number_total             1756
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201781x_si_003.cif
_cod_data_source_block           k11245
_cod_database_code               4026725