Desymmetrization of unactivated bis-alkenes via chiral Brønsted acid-catalysed hydroamination
Yu, Zhang-Long; Cheng, Yong-Feng; Jiang, Na-Chuan; Wang, Jian; Fan, Li-Wen; Yuan, Yue; Li, Zhong-Liang; Gu, Qiang-Shuai; Liu, Xin-Yuan; Chemical Science 11 (2020) 5987–5993; doi:10.1039/D0SC00001A

data_1558092
_publ_section_title
;
 Desymmetrization of unactivated bis-alkenes via chiral Br\/onsted
 acid-catalysed hydroamination
;
_journal_issue                   23
_journal_name_full               'Chemical Science'
_journal_page_first              5987
_journal_page_last               5993
_journal_paper_doi               10.1039/D0SC00001A
_journal_volume                  11
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C33 H28 F6 N2 S2'
_chemical_formula_sum            'C33 H28 F6 N2 S2'
_chemical_formula_weight         630.69
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-04
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-07-03 deposited with the CCDC.	2020-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.158(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.6734(7)
_cell_length_b                   13.4920(9)
_cell_length_c                   10.8926(8)
_cell_measurement_reflns_used    9799
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.502
_cell_measurement_theta_min      2.363
_cell_volume                     1506.63(18)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            37838
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_min         2.363
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0954 before and 0.0506 after correction. The Ratio of minimum to maximum transmission is 0.9514. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       block
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 2985 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.017(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         6927
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0276
_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^)+(0.0344P)^2^+0.3240P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0664
_refine_ls_wR_factor_ref         0.0679
_reflns_Friedel_coverage         0.916
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                6575
_reflns_number_total             6927
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc00001a2.cif
_cod_data_source_block           mo_cxy0138_0m
_cod_depositor_comments
;Adding full bibliography for 1558092.cif.

 Adding full bibliography for 1558092.cif.
;
_cod_database_code               1558092
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.919
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.88 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C20(H20A,H20B), C25(H25A,H25B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C21(H21), C23(H23), C24(H24), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33)
3.c X=CH2 refined with riding coordinates:
 C27(H27A,H27B)
3.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              51943
_olex2_submission_special_instructions 'No special instructions were received'