Mechanistic Insight into Self-Propagation of Organo-Mediated Beckmann Rearrangement: A Combined Experimental and Computational Study
Na An; Bo-Xue Tian; Hong-Jun Pi; Leif A. Eriksson; Wei-Ping Deng; Journal of Organic Chemistry 78 (2013) 4297–4302; doi:10.1021/jo400278c

data_4028196
_publ_section_title
;
 Mechanistic Insight into Self-Propagation of Organo-Mediated Beckmann
 Rearrangement: A Combined Experimental and Computational Study
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4297
_journal_page_last               4302
_journal_paper_doi               10.1021/jo400278c
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C26 H20 N2 O'
_chemical_formula_weight         376.44
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_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
_cell_angle_alpha                83.155(7)
_cell_angle_beta                 75.634(5)
_cell_angle_gamma                62.657(4)
_cell_formula_units_Z            2
_cell_length_a                   10.010(3)
_cell_length_b                   10.641(5)
_cell_length_c                   10.743(3)
_cell_measurement_reflns_used    836
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.240
_cell_measurement_theta_min      2.347
_cell_volume                     984.7(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0635
_diffrn_reflns_av_sigmaI/netI    0.0985
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4097
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9969
_exptl_absorpt_correction_T_min  0.9884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       needle
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.869
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.869
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0691
_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^)+(0.0971P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1679
_refine_ls_wR_factor_ref         0.1890
_reflns_number_gt                1594
_reflns_number_total             3392
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400278c_si_002.cif
_cod_data_source_block           a00604a
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