Synthesis of 1,3-Dihydrobenzo[c]furans from Ortho-Lithiated Aryloxiranes
Vito Capriati; Saverio Florio; Renzo Luisi; Filippo M. Perna; Antonio Salomone; Journal of Organic Chemistry 71 (2006) 3984–3987; doi:10.1021/jo052645t

data_4021680
_publ_contact_author
;Prof. Saverio Florio

;
_publ_contact_author_address
;Dipartimento Farmaco-Chimico
Universit\`a degli Studi di Bari
via E. Orabona 4
70125 Bari Ba
Italy
;
_publ_contact_author_email       florio@farmchim.uniba.it
_publ_contact_author_fax         '39 080 5442231'
_publ_contact_author_phone       '39 080 5442749'
_publ_section_title
;
 Synthesis of 1,3-Dihydrobenzo[c]furans from
 Ortho-Lithiated Aryloxiranes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3984
_journal_page_last               3987
_journal_paper_doi               10.1021/jo052645t
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C34 H36 O4'
_chemical_formula_weight         508.63
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 93.5900(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9090(2)
_cell_length_b                   13.4390(2)
_cell_length_c                   22.0690(4)
_cell_measurement_reflns_used    4928
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.77
_cell_measurement_theta_min      0.92
_cell_volume                     2933.10(9)
_computing_cell_refinement
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD (Bruker-Nonius, 1998)'
_computing_data_reduction
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Phi scan'
_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  0.098
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4667
_diffrn_reflns_theta_full        24.77
_diffrn_reflns_theta_max         24.77
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .05
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.066(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.0878
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1294P)^2^+3.9118P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2571
_refine_ls_wR_factor_ref         0.2771
_reflns_number_gt                3372
_reflns_number_total             4667
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo052645tsi20051223_014633.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4021680