Studies toward the Synthesis of 4-(2-R-ethyl)amino-2,2,5,5-tetramethyl-3-imidazoline 1-Oxyls. Nucleophilic Substitution of Bromide in the N-Alkyl Chain of the 1,2,4-Oxadiazol-2-one Precursor
Julya F. Polienko; Thomas Schanding; Yury V. Gatilov; Igor A. Grigor'ev; Maxim A. Voinov; Journal of Organic Chemistry 73 (2008) 502–510; doi:10.1021/jo701803a

data_4023194
_publ_contact_author
;       Maxim A. Voinov
        North Carolina State University
        College of Physical and
        Mathematical Sciences
        Campus Box 8204
        Raleigh, NC 27695-8204
        USA
;
_publ_contact_author_email       mvoynov@ncsu.edu
_publ_contact_author_fax         '(919) 513 7353'
_publ_contact_author_phone       '(919) 515 3209'
_publ_section_title
;
 Studies toward the Synthesis of
 4-(2-R-ethyl)amino-2,2,5,5-tetramethyl-3-imidazoline 1-Oxyls.
 Nucleophilic Substitution of Bromide in the N-Alkyl Chain of
 the 1,2,4-Oxadiazol-2-one Precursor
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              502
_journal_page_last               510
_journal_paper_doi               10.1021/jo701803a
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C10 H17 N4 O S'
_chemical_formula_sum            'C10 H17 N4 O S'
_chemical_formula_weight         241.34
_chemical_melting_point          413
_chemical_name_systematic
; 
 2',2',5',5'-tetramethyl-1'-oxyl-4,5,2',5'-tetrahydro-3H,1'H-
 [1,4']biimidazolyl-2-thione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.270(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2974(14)
_cell_length_b                   15.2206(13)
_cell_length_c                   11.3294(13)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      13.31
_cell_measurement_theta_min      12.5
_cell_volume                     1224.8(3)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '2\q/\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2585
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         2.28
_diffrn_standards_decay_%        1.00
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.8695
_exptl_absorpt_correction_T_min  0.8479
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.70
_exptl_crystal_size_min          0.60
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.029(3)
_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   1.069
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         2394
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0537P)^2^+0.4044P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1083
_reflns_number_gt                2246
_reflns_number_total             2394
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701803a-File002.cif
_cod_data_source_block           compound_14_Voinov
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023194