Chemo- and Diastereoselective Synthesis of N-Propargyl Oxazolidines through a Copper-Catalyzed Domino A<sup>3</sup> Reaction.
Zhang, Yazhen; Huang, Liliang; Li, Xiaoyang; Wang, Le; Feng, Huangdi; The Journal of organic chemistry 84 (2019) 5046–5055; doi:10.1021/acs.joc.8b03244

data_4034348
_publ_section_title
;
 Chemo- and Diastereoselective Synthesis of N-Propargyl Oxazolidines
 through a Copper-Catalyzed Domino A<sup>3</sup> Reaction.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5046
_journal_page_last               5055
_journal_paper_doi               10.1021/acs.joc.8b03244
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C24 H21 N O'
_chemical_formula_sum            'C24 H21 N O'
_chemical_formula_weight         339.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-11-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                71.312(4)
_cell_angle_beta                 76.320(4)
_cell_angle_gamma                87.190(4)
_cell_formula_units_Z            2
_cell_length_a                   9.5434(15)
_cell_length_b                   10.2429(15)
_cell_length_c                   10.6535(15)
_cell_measurement_reflns_used    2071
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.14
_cell_measurement_theta_min      2.44
_cell_volume                     958.1(2)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9067
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.061
_diffrn_reflns_theta_min         2.197
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6378
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0524 before and 0.0380 after correction. The Ratio of minimum to maximum transmission is 0.8550. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         5507
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1697
_refine_ls_R_factor_gt           0.0901
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+0.8829P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1928
_refine_ls_wR_factor_ref         0.2250
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2824
_reflns_number_total             5507
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03244_si_002.cif
_cod_data_source_block           3135_0m
_cod_database_code               4034348
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Shared sites
{O15, C14A}
{C14, O15A}
3. Uiso/Uaniso restraints and constraints
Uanis(O15) = Uanis(C14A)
Uanis(C14) = Uanis(O15A)
4. Others
 Sof(O15A)=Sof(H7B)=Sof(H8B)=Sof(C14A)=Sof(H14C)=Sof(H14D)=1-FVAR(1)
 Sof(O15)=Sof(H7A)=Sof(H8A)=Sof(C14)=Sof(H14A)=Sof(H14B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C7(H7A), C7(H7B), C8(H8A), C8(H8B)
5.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C14(H14A,H14B), C14A(H14C,H14D)
5.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C12(H12), C13(H13), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
;
_shelx_res_checksum              96736
_shelx_hkl_checksum              76678
_olex2_submission_special_instructions 'No special instructions were received'