Catalytic intramolecular aminoarylation of unactivated alkenes with aryl sulfonamides
Noten, Efrey A.; McAtee, Rory C.; Stephenson, Corey R. J.; Chemical Science  (2022) –; doi:10.1039/D2SC01228F

data_1567019
_publ_section_title
;
 Catalytic intramolecular aminoarylation of unactivated alkenes with aryl
 sulfonamides
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC01228F
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H13 F2 N O'
_chemical_formula_sum            'C12 H13 F2 N O'
_chemical_formula_weight         225.23
_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   mixed
_atom_sites_solution_primary     dual-space
_atom_sites_solution_secondary   ?difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-11-20 deposited with the CCDC.	2022-05-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.32492(6)
_cell_length_b                   7.77679(5)
_cell_length_c                   18.64270(13)
_cell_measurement_reflns_used    13269
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      69.3430
_cell_measurement_theta_min      4.7230
_cell_volume                     1061.970(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      85(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16093
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.368
_diffrn_reflns_theta_min         4.744
_diffrn_source                   'micro-focus rotating anode'
_exptl_absorpt_coefficient_mu    0.964
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93266
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
; 
 Flack x determined using 790 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 

 While the Flack and Hooft statistics are somewhat ambigious, the
 Biovet analysis via PLATON is more definitive.

Bayesian Statistics
Student_T Nu       76
Select Pairs      798
Theta_Min ..     8.65
Theta_Max ..    69.21
P2(true)....    1.000
P3(true)....    1.000
P3(rac-twin)  0.3E-03
P3(false) ..  0.1E-61
G ..........   0.5645
G (su) .....   0.0886
Hooft y ....  0.22(4)

;
_refine_ls_abs_structure_Flack   0.23(5)
_refine_ls_extinction_coef       0.0066(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         1976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0269
_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^)+(0.0433P)^2^+0.1608P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0698
_refine_ls_wR_factor_ref         0.0699
_reflns_Friedel_coverage         0.677
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                1969
_reflns_number_total             1976
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01228f2.cif
_cod_data_source_block           ean223
_cod_original_cell_volume        1061.969(14)
_cod_database_code               1567019
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.861
_shelx_estimated_absorpt_t_max   0.910
_shelx_res_checksum              98283