Lewis Basic Sulfide Catalyzed Electrophilic Bromocyclization of Cyclopropylmethyl Amide.
Wong, Ying-Chieh; Ke, Zhihai; Yeung, Ying-Yeung; Organic letters 17 (2015) 4944–4947; doi:10.1021/acs.orglett.5b02557

data_1555353
_publ_section_title
;
 Lewis Basic Sulfide Catalyzed Electrophilic Bromocyclization of
 Cyclopropylmethyl Amide.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              4944
_journal_page_last               4947
_journal_paper_doi               10.1021/acs.orglett.5b02557
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C21 H24 Br N O'
_chemical_formula_sum            'C21 H24 Br N O'
_chemical_formula_weight         386.32
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                72.212(2)
_cell_angle_beta                 72.822(2)
_cell_angle_gamma                85.148(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3568(5)
_cell_length_b                   9.1260(6)
_cell_length_c                   13.2967(8)
_cell_measurement_reflns_used    3411
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.341
_cell_measurement_theta_min      2.344
_cell_volume                     922.49(10)
_computing_cell_refinement
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_collection       'APEX v2014.11.0'
_computing_data_reduction        'Saint, APEX v2014.11.0.'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX v2014.11.0.'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT, Acta Cryst., Sect. A 2015, A71, 3-8.'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from \q/2\q scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            37525
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.341
_diffrn_reflns_theta_min         2.344
_exptl_absorpt_coefficient_mu    2.235
_exptl_absorpt_correction_T_max  0.696
_exptl_absorpt_correction_T_min  0.612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       'prism frag'
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.175
_refine_diff_density_max         1.658
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4588
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0312P)^2^+1.3607P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0814
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4086
_reflns_number_total             4588
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02557_si_001.cif
_cod_data_source_block           shelx
_cod_database_code               1555353
_shelx_estimated_absorpt_t_min   0.612
_shelx_estimated_absorpt_t_max   0.696
_shelxl_version_number           2014/6
_shelx_res_checksum              57940
_shelx_hkl_checksum              4650