Chiral N,N′-dioxide/Mg(OTf)2 complex-catalyzed asymmetric [2,3]-rearrangement of in situ generated ammonium salts
Lin, Qianchi; Hu, Bowen; Xu, Xi; Dong, Shunxi; Liu, Xiaohua; Feng, Xiaoming; Chemical Science 11 (2020) 3068–3073; doi:10.1039/C9SC06342K

data_1557341
_publ_section_title
;
 Chiral N,N&#x2032;-dioxide/Mg(OTf)2 complex-catalyzed asymmetric
 [2,3]-rearrangement of in situ generated ammonium salts
;
_journal_issue                   11
_journal_name_full               'Chemical Science'
_journal_page_first              3068
_journal_page_last               3073
_journal_paper_doi               10.1039/C9SC06342K
_journal_volume                  11
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C15 H21 Cl0 N O2'
_chemical_formula_weight         247.33
_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
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-10-23 deposited with the CCDC.	2020-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5161(5)
_cell_length_b                   10.5750(6)
_cell_length_c                   15.9557(9)
_cell_measurement_reflns_used    9006
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      68.44
_cell_measurement_theta_min      2.77
_cell_volume                     1436.93(14)
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'BRUKER D8 VENTURE PHOTON II'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9239
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.431
_diffrn_reflns_theta_min         5.017
_exptl_absorpt_coefficient_mu    0.597
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             536
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.113
_refine_diff_density_rms         0.023
_refine_ls_abs_structure_details
;
 Flack x determined using 1050 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2537
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0630P)^2^+0.1459P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0922
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                2531
_reflns_number_total             2537
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc06342k2.cif
_cod_data_source_block           cu_LQC20190608_1_0m_a
_cod_depositor_comments
;Adding full bibliography for 1557341.cif.

 Adding full bibliography for 1557341.cif.
;
_cod_database_code               1557341
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              54869