Dearomatization-bis-alkylation of aromatic and heteroaromatic diesters promoted by Me3SnLi via a stanna-Brook rearrangement.
Monje, Pablo; Graña, Paula; Paleo, M. Rita; Sardina, F. Javier; Organic letters 8 (2006) 951–954; doi:10.1021/ol053130r

data_1505871
_publ_section_title
;
 Dearomatization-bis-alkylation of aromatic and heteroaromatic diesters
 promoted by Me3SnLi via a stanna-Brook rearrangement.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              951
_journal_page_last               954
_journal_paper_doi               10.1021/ol053130r
_journal_volume                  8
_journal_year                    2006
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C11 H16 O2'
_chemical_formula_sum            'C11 H16 O2'
_chemical_formula_weight         180.24
_chemical_name_systematic
;
 (7a-Hydroxymethyl-1,2,3,7a-tetrahydro-inden-3a-yl)-methanol
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2005-12-01T11:58:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                104.494(5)
_cell_angle_beta                 91.160(8)
_cell_angle_gamma                101.957(12)
_cell_formula_units_Z            4
_cell_length_a                   7.8294(13)
_cell_length_b                   11.3508(15)
_cell_length_c                   11.6799(5)
_cell_measurement_reflns_used    10
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.4225
_cell_measurement_theta_min      7.1095
_cell_measurement_wavelength     1.5418
_cell_volume                     980.3(2)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia,1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_orient_matrix_type
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      -0.04755
_diffrn_orient_matrix_UB_12      -0.088493
_diffrn_orient_matrix_UB_13      -0.045403
_diffrn_orient_matrix_UB_21      -0.07923
_diffrn_orient_matrix_UB_22      0.028326
_diffrn_orient_matrix_UB_23      -0.050563
_diffrn_orient_matrix_UB_31      0.092714
_diffrn_orient_matrix_UB_32      0.007753
_diffrn_orient_matrix_UB_33      -0.057002
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3719
_diffrn_reflns_theta_full        70.07
_diffrn_reflns_theta_max         70.07
_diffrn_reflns_theta_min         3.92
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        6
_diffrn_standards_interval_count 138
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  0.9742
_exptl_absorpt_correction_T_min  0.8029
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
        Number of psi-scan sets used was   7
        Theta correction was applied.
        Weighted transmission curves were used.
        No Fourier smoothing was applied.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3719
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.1575
_refine_ls_R_factor_gt           0.0977
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1892P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2413
_refine_ls_wR_factor_ref         0.2667
_reflns_number_gt                2113
_reflns_number_total             3719
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol053130rsi20051229_051443.cif
_cod_data_source_block           js01pm1
_cod_database_code               1505871