Asymmetric alkylation of remote C(sp3)‒H bonds by combining proton-coupled electron transfer with chiral Lewis acid catalysis
Yuan, Wei; Zhou, Zijun; Gong, Lei; Meggers, Eric; Chem. Commun.  (2017) –; doi:10.1039/C7CC04941B

data_7120495
_publ_section_title
;
 Asymmetric alkylation of remote C(sp3)--H bonds by combining
 proton-coupled electron transfer with chiral Lewis acid catalysis
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC04941B
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C30 H33 Br N O4'
_chemical_formula_sum            'C30 H33 Br N O4'
_chemical_formula_weight         551.48
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-06-05 deposited with the CCDC.
2017-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.438(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.1916(9)
_cell_length_b                   5.8015(3)
_cell_length_c                   16.4573(7)
_cell_measurement_reflns_used    3228
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      73.6730
_cell_measurement_theta_min      3.990
_cell_volume                     1352.53(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_sigmaI/netI    0.0647
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8782
_diffrn_reflns_theta_full        61.16
_diffrn_reflns_theta_max         61.16
_diffrn_reflns_theta_min         4.00
_exptl_absorpt_coefficient_mu    2.352
_exptl_absorpt_correction_T_max  0.7655
_exptl_absorpt_correction_T_min  0.6768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41o (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             574
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.589
_refine_diff_density_min         -1.119
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(7)
_refine_ls_extinction_coef       0.0025(13)
_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   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         3917
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1245
_refine_ls_R_factor_gt           0.0830
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2296P)^2^+3.1817P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2551
_refine_ls_wR_factor_ref         0.3480
_reflns_number_gt                2691
_reflns_number_total             3917
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc04941b2.cif
_cod_data_source_block           yw
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7120495