Ketones and Aldehydes as O-Nucleophiles in Iridium-Catalyzed Intramolecular Asymmetric Allylic Substitution Reaction.
Wang, Ye; Zhang, Wen-Yun; You, Shu-Li; Journal of the American Chemical Society 141 (2019) 2228–2232; doi:10.1021/jacs.8b13182

data_4128162
_publ_section_title
;
 Ketones and Aldehydes as O-Nucleophiles in Iridium-Catalyzed
 Intramolecular Asymmetric Allylic Substitution Reaction.
;
_journal_issue                   6
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2228
_journal_page_last               2232
_journal_paper_doi               10.1021/jacs.8b13182
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C19 H18 N2 O5 S'
_chemical_formula_sum            'C19 H18 N2 O5 S'
_chemical_formula_weight         386.41
_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'
_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     dual
_audit_creation_date             2019-01-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.608(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9205(7)
_cell_length_b                   6.7662(4)
_cell_length_c                   23.3600(14)
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.98
_cell_measurement_theta_min      3.23
_cell_volume                     1882.18(19)
_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      170
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.981
_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  0.0760
_diffrn_reflns_av_unetI/netI     0.0867
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            20544
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.027
_diffrn_reflns_theta_min         3.229
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.178
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1636 before and 0.0819 after correction. The Ratio of minimum to maximum transmission is 0.6401. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 2329 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         7061
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0610P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1299
_reflns_Friedel_coverage         0.829
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                6057
_reflns_number_total             7061
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b13182_si_004.cif
_cod_data_source_block           mj19067_0m
_cod_database_code               4128162
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.872
_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.a Ternary CH refined with riding coordinates:
 C1(H1), C1A(H1A)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C2A(H2AA,H2AB)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15),
 C17(H17), C18(H18), C3A(H3A), C5A(H5A), C9A(H9A), C10A(H10A), C11A(H11A),
 C12A(H12A), C14A(H14A), C15A(H15A), C17A(H17A), C18A(H18A)
2.d X=CH2 refined with riding coordinates:
 C6(H6A,H6B), C6A(H6AA,H6AB)
2.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C19A(H19D,H19E,H19F)
;
_shelx_res_checksum              6852
_shelx_hkl_checksum              84470
_olex2_submission_special_instructions 'No special instructions were received'