Synthesis of 2,5-Bis(spirocyclohexane)-Substituted Nitroxides of Pyrroline and Pyrrolidine Series, Including Thiol-Specific Spin Label: An Analogue of MTSSL with Long Relaxation Time
Igor A. Kirilyuk; Yuliya F. Polienko; Olesya A. Krumkacheva; Rodion K. Strizhakov; Yurii V. Gatilov; Igor A. Grigor'ev; Elena G. Bagryanskaya; Journal of Organic Chemistry 77 (2012) 8016–8027; doi:10.1021/jo301235j

data_4027516
_publ_contact_author_address
;Novosibirsk Institute of Organic Chemistry SB RAS, 
Lavrentjev Ave. 9, 630090, Novosibirsk, Russian Federation
;
_publ_contact_author_email       gatilov@nioch.nsc.ru
_publ_contact_author_name        'Dr. Yu.V. Gatilov'
_publ_section_title
;
 Synthesis of 2,5-Bis(spirocyclohexane)-Substituted Nitroxides of
 Pyrroline and Pyrrolidine Series, Including Thiol-Specific Spin Label: An
 Analogue of MTSSL with Long Relaxation Time
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8016
_journal_page_last               8027
_journal_paper_doi               10.1021/jo301235j
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C16 H22 N3 O'
_chemical_formula_sum            'C16 H22 N3 O'
_chemical_formula_weight         272.37
_chemical_melting_point          449
_chemical_name_systematic
; 
 14R(S),15R(S)-14,15-dicyano-7-azadispiro[5.1.5.2]pentadecane-7-oxyl 
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2386(8)
_cell_length_b                   24.0533(17)
_cell_length_c                   6.5901(5)
_cell_measurement_reflns_used    5030
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.01
_cell_measurement_theta_min      2.36
_cell_volume                     1464.4(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0102
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6444
_diffrn_reflns_theta_full        30.04
_diffrn_reflns_theta_max         30.04
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9703
_exptl_absorpt_correction_T_min  0.8842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       prism
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3825
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0533P)^2^+0.2489P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0980
_reflns_number_gt                3739
_reflns_number_total             3825
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301235j_si_001_3.cif
_cod_data_source_block           compound16_nl1213
_cod_database_code               4027516