Asymmetric synthesis of trans-dihydroarylfurans in a Friedel-Crafts/substitution domino reaction under squaramide catalysis.
Jarava-Barrera, Carlos; Esteban, Francisco; Navarro-Ranninger, Carmen; Parra, Alejandro; Alemán, José; Chemical communications (Cambridge, England) 49 (2013) 2001–2003; doi:10.1039/c2cc38534a

data_7112376
_publ_section_title
;
 Asymmetric synthesis of trans-dihydroarylfurans in a
 Friedel-Crafts/substitution domino reaction under squaramide catalysis.
;
_journal_issue                   20
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2001
_journal_page_last               2003
_journal_paper_doi               10.1039/c2cc38534a
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C18 H12 Br N O3'
_chemical_formula_weight         370.20
_chemical_name_common            CJ143
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.0050(11)
_cell_length_b                   12.3558(14)
_cell_length_c                   28.675(3)
_cell_measurement_reflns_used    6137
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      22.0990
_cell_measurement_theta_min      2.3706
_cell_volume                     3190.5(6)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            27019
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    2.591
_exptl_absorpt_correction_T_max  0.65
_exptl_absorpt_correction_T_min  0.47
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.463
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.013(10)
_refine_ls_extinction_coef       0.0065(6)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5842
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0678P)^2^+0.9214P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1279
_reflns_number_gt                4131
_reflns_number_total             5842
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7108905
_cod_data_source_file            c2cc38534a.txt
_cod_data_source_block           2
_cod_database_code               7112376