Additions of Organomagnesium Halides to α-Alkoxy Ketones: Revision of the Chelation-Control Model.
Read, Jacquelyne A.; Yang, Yingying; Woerpel, K. A.; Organic letters 19 (2017) 3346–3349; doi:10.1021/acs.orglett.7b01161

data_1547093
_publ_section_title
;
 Additions of Organomagnesium Halides to \a-Alkoxy Ketones: Revision of
 the Chelation-Control Model.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3346
_journal_page_last               3349
_journal_paper_doi               10.1021/acs.orglett.7b01161
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration rm
_chemical_formula_sum            'C21 H22 N2 O7'
_chemical_formula_weight         414.40
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                79.535(12)
_cell_angle_beta                 87.356(11)
_cell_angle_gamma                75.611(10)
_cell_formula_units_Z            2
_cell_length_a                   7.500(7)
_cell_length_b                   10.984(10)
_cell_length_c                   12.966(12)
_cell_measurement_reflns_used    1060
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.11
_cell_measurement_theta_min      2.30
_cell_volume                     1017.4(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0866
_diffrn_reflns_av_unetI/netI     0.1485
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5930
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        21.985
_diffrn_reflns_theta_max         21.985
_diffrn_reflns_theta_min         1.597
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7447
_exptl_absorpt_correction_T_min  0.5439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       plate
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 890 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     545
_refine_ls_number_reflns         4752
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1368
_refine_ls_R_factor_gt           0.0722
_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^)+(0.0658P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1502
_refine_ls_wR_factor_ref         0.1833
_reflns_Friedel_coverage         0.929
_reflns_Friedel_fraction_full    0.919
_reflns_Friedel_fraction_max     0.919
_reflns_number_gt                2796
_reflns_number_total             4752
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01161_si_002.cif
_cod_data_source_block           16kaw1h
_cod_database_code               1547093
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.947
_shelx_estimated_absorpt_t_max   0.999
_shelx_res_checksum              36216
_shelx_hkl_checksum              15800