Photoinduced Wolff rearrangement/Pd-catalyzed [3+2] cycloaddition sequence: an unexpected route to tetrahydrofurans
Lu, Liang-Qiu; Liu, Jie; Li, Miao-Miao; Qu, Bao-Le; Xiao, Wen-Jing; Chemical Communications  (2019) –; doi:10.1039/C8CC10157D

data_7122890
_publ_section_title
;
 Photoinduced Wolff rearrangement/Pd-catalyzed [3+2] cycloaddition
 sequence: an unexpected route to tetrahydrofurans
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC10157D
_journal_year                    2019
_chemical_formula_sum            'C16 H13 Br N2 O'
_chemical_formula_weight         329.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-07-13 deposited with the CCDC.
2019-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.9770(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3670(4)
_cell_length_b                   11.7885(3)
_cell_length_c                   8.5930(3)
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      60.58
_cell_measurement_theta_min      2.90
_cell_volume                     1541.59(8)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
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_diffrn_reflns_limit_l_min       -8
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_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        60.929
_diffrn_reflns_theta_max         60.929
_diffrn_reflns_theta_min         2.904
_exptl_absorpt_coefficient_mu    3.606
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.150
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_refine_diff_density_max         0.581
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_restraints     0
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_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0592
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0825P)^2^+1.6903P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1674
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_reflns_number_gt                2153
_reflns_number_total             2265
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc10157d2.cif
_cod_data_source_block           cu_180328D_0m
_cod_database_code               7122890
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.614
_shelx_estimated_absorpt_t_max   0.714
_shelx_res_checksum              67271