Intramolecular [3 + 2]-cycloadditions of azomethine ylides derived from secondary amines via redox-neutral C-H functionalization.
Mantelingu, Kempegowda; Lin, Yingfu; Seidel, Daniel; Organic letters 16 (2014) 5910–5913; doi:10.1021/ol502918g

data_1518181
_publ_section_title
;
 Intramolecular [3 + 2]-cycloadditions of azomethine ylides derived from
 secondary amines via redox-neutral C-H functionalization.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5910
_journal_page_last               5913
_journal_paper_doi               10.1021/ol502918g
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C17 H19 Br2 N O3'
_chemical_formula_weight         445.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 99.522(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.5493(10)
_cell_length_b                   15.5828(15)
_cell_length_c                   21.010(2)
_cell_measurement_reflns_used    6286
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.54
_cell_measurement_theta_min      2.35
_cell_volume                     3406.2(6)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            18625
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.031
_diffrn_reflns_theta_min         2.354
_exptl_absorpt_coefficient_mu    4.773
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.5069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SAINT (SADABS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.736
_exptl_crystal_description       lathe
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          .45
_exptl_crystal_size_mid          .35
_exptl_crystal_size_min          .12
_refine_diff_density_max         1.059
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         5915
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0286
_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^)+(0.0370P)^2^+2.8000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0731
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4875
_reflns_number_total             5915
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol502918g_si_003.cif
_cod_data_source_block           mk53_C2c
_cod_depositor_comments
'Adding full bibliography for 1518180--1518183.cif.'
_cod_database_code               1518181
_shelxl_version_number           2013-4
_shelx_res_checksum              39938
_shelx_hkl_checksum              59168