Light-Mediated Asymmetric Aliphatic C–H Alkylation with Hydrogen Atom Transfer Catalyst and Chiral Phosphoric Acid
Dai, Zhen-Yao; Nong, Zhong-Sheng; Wang, Pu-Sheng; ACS Catalysis 10 (2020) 4786–4790; doi:10.1021/acscatal.0c00610

data_4517547
_publ_section_title
;
 Light-Mediated Asymmetric Aliphatic C--H Alkylation with Hydrogen Atom
 Transfer Catalyst and Chiral Phosphoric Acid
;
_journal_issue                   8
_journal_name_full               'ACS Catalysis'
_journal_page_first              4786
_journal_page_last               4790
_journal_paper_doi               10.1021/acscatal.0c00610
_journal_volume                  10
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C17 H22 O2'
_chemical_formula_sum            'C17 H22 O2'
_chemical_formula_weight         258.34
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 113.939(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2490(8)
_cell_length_b                   6.1775(3)
_cell_length_c                   16.2653(9)
_cell_measurement_reflns_used    2060
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.78
_cell_measurement_theta_min      7.62
_cell_volume                     1400.40(13)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15994
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.037
_diffrn_reflns_theta_min         2.758
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.395
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1961 before and 0.0800 after correction. The Ratio of minimum to maximum transmission is 0.4543. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.006
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1374 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.20(18)
_refine_ls_extinction_coef       0.0073(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         5138
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0652
_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^)+(0.0724P)^2^+0.9562P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.1739
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_full    0.934
_reflns_Friedel_fraction_max     0.923
_reflns_number_gt                4087
_reflns_number_total             5138
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c00610_si_002.cif
_cod_data_source_block           191220dzy_0m
_cod_depositor_comments
;Adding full bibliography for 4517547.cif.

 Adding full bibliography for 4517547.cif.
;
_cod_database_code               4517547
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.962
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C12(H12), C1A(H1AB), C12A(H12A)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B),
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C9A(H9AA,H9AB), C10A(H10C,
 H10D), C11A(H11C,H11D), C13A(H13C,H13D), C14A(H14C,H14D), C15A(H15C,H15D),
 C16A(H16C,H16D), C17A(H17C,H17D)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C4A(H4A), C6A(H6A), C7A(H7A)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O1A(H1AA)
;
_shelx_res_checksum              13321
_shelx_hkl_checksum              20819
_olex2_submission_special_instructions 'No special instructions were received'