Regiocontrolled rearrangement of isobenzofurans.
Egan, Ben A.; Paradowski, Michael; Thomas, Lynne H.; Marquez, Rodolfo; Organic letters 13 (2011) 2086–2089; doi:10.1021/ol200498k

data_1502110
_publ_section_title
;
 Regiocontrolled rearrangement of isobenzofurans.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              2086
_journal_page_last               2089
_journal_paper_doi               10.1021/ol200498k
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C22 H31 N O5 Si'
_chemical_formula_weight         417.57
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-09-13T15:39:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7398(3)
_cell_length_b                   8.2057(2)
_cell_length_c                   25.4880(9)
_cell_measurement_reflns_used    6688
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      62.5231
_cell_measurement_theta_min      3.4652
_cell_volume                     2246.20(11)
_computing_cell_refinement
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
        (compiled Jan  5 2010,16:28:46)
;
_computing_data_collection
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
        (compiled Jan  5 2010,16:28:46)
;
_computing_data_reduction
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
        (compiled Jan  5 2010,16:28:46)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4383
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0298049
_diffrn_orient_matrix_UB_12      -0.1026245
_diffrn_orient_matrix_UB_13      -0.0410969
_diffrn_orient_matrix_UB_21      0.1177362
_diffrn_orient_matrix_UB_22      0.0869027
_diffrn_orient_matrix_UB_23      -0.0295196
_diffrn_orient_matrix_UB_31      0.1431916
_diffrn_orient_matrix_UB_32      -0.0501197
_diffrn_orient_matrix_UB_33      0.0329979
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.062
_diffrn_reflns_av_unetI/netI     0.045
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            14532
_diffrn_reflns_theta_full        61.99
_diffrn_reflns_theta_max         61.99
_diffrn_reflns_theta_min         3.47
_exptl_absorpt_coefficient_mu    1.186
_exptl_absorpt_correction_T_max  0.905
_exptl_absorpt_correction_T_min  0.846
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
        (compiled Jan  5 2010,16:28:46)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.04
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         3524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0434P)^2^+0.3129P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0919
_reflns_number_gt                2907
_reflns_number_total             3524
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol200498k_si_006.cif
_cod_data_source_block           be415b
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1502110