Bypassing the stereoselectivity issue: transformations of Kinugasa adducts from chiral alkynes and non-chiral acyclic nitrones.
Kutaszewicz, Rafał; Grzeszczyk, Barbara; Górecki, Marcin; Staszewska-Krajewska, Olga; Furman, Bartłomiej; Chmielewski, Marek; Organic & biomolecular chemistry 17 (2019) 6251–6268; doi:10.1039/c9ob00940j

data_7156888
_publ_section_title
;
 Bypassing the stereoselectivity issue: transformations of Kinugasa
 adducts from chiral alkynes and non-chiral acyclic nitrones.
;
_journal_issue                   25
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6251
_journal_page_last               6268
_journal_paper_doi               10.1039/c9ob00940j
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C16 H21 N O6'
_chemical_formula_sum            'C16 H21 N O6'
_chemical_formula_weight         323.34
_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'
_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-2014
_audit_update_record
;
2018-11-13 deposited with the CCDC.    2019-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.698(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.4441(3)
_cell_length_b                   18.1287(8)
_cell_length_c                   8.5243(4)
_cell_measurement_reflns_used    1551
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.58
_cell_measurement_theta_min      4.88
_cell_volume                     837.14(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.768
_diffrn_measured_fraction_theta_max 0.784
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.768
_diffrn_reflns_Laue_measured_fraction_max 0.784
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5201
_diffrn_reflns_point_group_measured_fraction_full 0.773
_diffrn_reflns_point_group_measured_fraction_max 0.789
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.583
_diffrn_reflns_theta_min         4.879
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.824
_exptl_absorpt_correction_T_max  0.8430
_exptl_absorpt_correction_T_min  0.7130
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.215
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.5(9)
_refine_ls_extinction_coef       0.0029(11)
_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   0.873
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         1983
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.873
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0645
_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^)+(0.0621P)^2^+2.4548P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1458
_refine_ls_wR_factor_ref         0.1886
_reflns_Friedel_coverage         0.945
_reflns_Friedel_fraction_full    0.778
_reflns_Friedel_fraction_max     0.794
_reflns_number_gt                1551
_reflns_number_total             1983
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00940j2.cif
_cod_data_source_block           BGZ_26_0m
_cod_depositor_comments          'Adding full bibliography for 7156888.cif.'
_cod_database_code               7156888
_shelx_estimated_absorpt_t_min   0.713
_shelx_estimated_absorpt_t_max   0.843
_shelxl_version_number           2014-3
_shelx_res_checksum              17559
_shelx_hkl_checksum              93207