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_1555751
_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            'C23 H29 Cl3 N2 O3 S'
_chemical_formula_weight         519.89
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8104(3)
_cell_length_b                   11.1726(3)
_cell_length_c                   21.1349(5)
_cell_measurement_reflns_used    4640
_cell_measurement_temperature    288(2)
_cell_measurement_theta_max      69.4040
_cell_measurement_theta_min      3.9630
_cell_volume                     2552.68(12)
_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      288(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.987
_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  0.0274
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9540
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.901
_diffrn_reflns_theta_min         4.476
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.236
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61470
_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    1.353
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.240
_refine_diff_density_max         0.780
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 1785 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.007(8)
_refine_ls_extinction_coef       0.0055(7)
_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   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4721
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0771
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0852P)^2^+2.4874P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1938
_refine_ls_wR_factor_ref         0.1985
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                4385
_reflns_number_total             4721
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02344_si_003.cif
_cod_data_source_block           shelxl
_cod_database_code               1555751
_shelx_estimated_absorpt_t_min   0.353
_shelx_estimated_absorpt_t_max   0.430
_shelxl_version_number           2013-4
_shelx_res_checksum              91662
_shelx_hkl_checksum              94535