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_4034807
_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         'C12 H23 N O3'
_chemical_formula_sum            'C12 H23 N O3'
_chemical_formula_weight         229.31
_chemical_melting_point          353
_chemical_name_systematic
; 
2,2,5-Triethyl-3,4-bis(hydroxymethyl)-3,4-dihydro-2H-pyrrole 1-oxide 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.9856(5)
_cell_length_b                   12.0156(5)
_cell_length_c                   15.6049(6)
_cell_measurement_reflns_used    9997
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.20
_cell_measurement_theta_min      2.59
_cell_volume                     2622.33(18)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0367
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            31162
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.886
_diffrn_reflns_theta_min         2.588
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9703
_exptl_absorpt_correction_T_min  0.9175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3125
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0505P)^2^+1.3449P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1419
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2513
_reflns_number_total             3125
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00085_si_002.cif
_cod_data_source_block           6-dsa075
_cod_database_code               4034807
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.954
_shelx_estimated_absorpt_t_max   0.980
_shelx_res_checksum              88639
_shelx_hkl_checksum              45526