Bond Rotation Dynamics of Enamides: The Effect of the Acyl Group and Potential for Chirality Transfer during 5-Endo Trig Radical Cyclizations
Andrew J. Clark; Dennis P. Curran; Joanna V. Geden; Natalie James; Paul Wilson; Journal of Organic Chemistry 76 (2011) 4546–4551; doi:10.1021/jo200343z

data_4026358
_publ_section_title
;
 Bond Rotation Dynamics of Enamides: The Effect of the Acyl Group and
 Potential for Chirality Transfer during 5-Endo Trig Radical Cyclizations
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4546
_journal_page_last               4551
_journal_paper_doi               10.1021/jo200343z
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C16 H20 Br N O'
_chemical_formula_weight         322.24
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_symmetry_space_group_name_H-M   'P b c a'
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_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.1009(3)
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_cell_length_c                   17.5284(4)
_cell_measurement_reflns_used    7201
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.10
_cell_measurement_theta_min      2.86
_cell_volume                     3010.09(11)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.2833
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
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_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14040
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         29.16
_diffrn_reflns_theta_min         2.89
_diffrn_standards_decay_%        nil
_exptl_absorpt_coefficient_mu    2.724
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSPACK(CrysAlis, Oxford Diffraction)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
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_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
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_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3691
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0541P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0948
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_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200343z_si_001.cif
_cod_data_source_block           pw3
_cod_original_cell_volume        3010.10(11)
_cod_database_code               4026358