Direct synthesis of highly functionalized furans from donor-acceptor cyclopropanes via DBU-mediated ring expansion reactions.
Su, Zhenjie; Xie, Zengyang; Wang, Shan; Luo, Naili; Wang, Cunde; Organic & biomolecular chemistry 17 (2019) 7342–7351; doi:10.1039/c9ob01308c

data_7156959
_publ_section_title
;
 Direct synthesis of highly functionalized furans from donor-acceptor
 cyclopropanes via DBU-mediated ring expansion reactions.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7342
_journal_page_last               7351
_journal_paper_doi               10.1039/c9ob01308c
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C18 H13 Br N2 O'
_chemical_formula_sum            'C18 H13 Br N2 O'
_chemical_formula_weight         353.20
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           Triclinic'
_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_creation_method           SHELXL-97
_audit_update_record
;
2019-04-08 deposited with the CCDC.    2019-07-08 downloaded from the CCDC.
;
_cell_angle_alpha                87.67(2)
_cell_angle_beta                 85.16(3)
_cell_angle_gamma                86.34(2)
_cell_formula_units_Z            2
_cell_length_a                   6.192(5)
_cell_length_b                   7.311(2)
_cell_length_c                   16.718(3)
_cell_measurement_reflns_used    5046
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.31
_cell_measurement_theta_min      2.43
_cell_volume                     752.1(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9835
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.22
_exptl_absorpt_coefficient_mu    2.736
_exptl_absorpt_correction_T_max  0.788
_exptl_absorpt_correction_T_min  0.729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocker
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.707
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2632
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0623
_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^)+(0.0474P)^2^+5.1536P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1719
_refine_ls_wR_factor_ref         0.1831
_reflns_number_gt                2114
_reflns_number_total             2646
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob01308c2.cif
_cod_data_source_block           001_a_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7156957--7156963.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7156959