Aryne-Mediated [2,3]-Sigmatropic Rearrangement of Tertiary Allylic Amines.
Zhang, Juan; Chen, Zhi-Xiong; Du, Ting; Li, Bing; Gu, Yonghong; Tian, Shi-Kai; Organic letters 18 (2016) 4872–4875; doi:10.1021/acs.orglett.6b02344

data_1555752
_publ_section_title
;
 Aryne-Mediated [2,3]-Sigmatropic Rearrangement of Tertiary Allylic
 Amines.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4872
_journal_page_last               4875
_journal_paper_doi               10.1021/acs.orglett.6b02344
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H26 Br N3 O3 S'
_chemical_formula_weight         492.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 95.598(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.1897(2)
_cell_length_b                   10.1219(3)
_cell_length_c                   12.6525(3)
_cell_measurement_reflns_used    2432
_cell_measurement_temperature    289(2)
_cell_measurement_theta_max      69.5320
_cell_measurement_theta_min      4.8290
_cell_volume                     1171.29(5)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      289(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4516
_diffrn_reflns_point_group_measured_fraction_full 0.679
_diffrn_reflns_point_group_measured_fraction_max 0.662
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.155
_diffrn_reflns_theta_min         4.835
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.448
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 625 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.029(15)
_refine_ls_extinction_coef       0.0052(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         2955
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0502P)^2^+0.0400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0967
_reflns_Friedel_coverage         0.301
_reflns_Friedel_fraction_full    0.339
_reflns_Friedel_fraction_max     0.326
_reflns_number_gt                2788
_reflns_number_total             2955
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02344_si_002.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1555752
_shelx_estimated_absorpt_t_min   0.405
_shelx_estimated_absorpt_t_max   0.468
_shelxl_version_number           2013-4
_shelx_res_checksum              3607
_shelx_hkl_checksum              54209