Synthesis of 3,4-Bis(hydroxymethyl)-2,2,5,5-tetraethylpyrrolidin-1-oxyl via 1,3-Dipolar Cycloaddition of Azomethine Ylide to Activated Alkene.
Dobrynin, Sergey A.; Glazachev, Yuri I.; Gatilov, Yuri V.; Chernyak, Elena I.; Salnikov, George E.; Kirilyuk, Igor A.; The Journal of organic chemistry 83 (2018) 5392–5397; doi:10.1021/acs.joc.8b00085

data_4034806
_publ_section_title
;
 Synthesis of 3,4-Bis(hydroxymethyl)-2,2,5,5-tetraethylpyrrolidin-1-oxyl
 via 1,3-Dipolar Cycloaddition of Azomethine Ylide to Activated Alkene.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5392
_journal_page_last               5397
_journal_paper_doi               10.1021/acs.joc.8b00085
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C14 H28 N O3'
_chemical_formula_sum            'C14 H28 N O3'
_chemical_formula_weight         258.37
_chemical_melting_point          334
_chemical_name_systematic
; 
2,2,5,5-Tetraethyl-3,4-bis(hydroxymethyl)pyrrolidin-1-oxyl 
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   32.1108(18)
_cell_length_b                   32.1108(18)
_cell_length_c                   8.1217(5)
_cell_measurement_reflns_used    9872
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.67
_cell_measurement_theta_min      3.17
_cell_volume                     7252.4(7)
_computing_cell_refinement       'Bruker SAINT'
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_computing_publication_material  'Bruker SHELXTL'
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_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_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  0.0504
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            51951
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.212
_diffrn_reflns_theta_min         1.268
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9538
_exptl_absorpt_correction_T_min  0.9173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.065
_exptl_crystal_description       prism
_exptl_crystal_F_000             2574
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.781
_refine_diff_density_rms         0.272
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3875
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1199
_refine_ls_R_factor_gt           0.0774
_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^)+(0.1957P)^2^+9.3115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2323
_refine_ls_wR_factor_ref         0.2916
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2930
_reflns_number_total             3875
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00085_si_003.cif
_cod_data_source_block           7-dsa082sq
_cod_original_cell_volume        7252.4(9)
_cod_database_code               4034806
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.984
_shelx_res_checksum              78601
_shelx_hkl_checksum              82635
_shelx_fab_checksum              72777