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_4027515
_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         'C15 H25 N2 O2, H2 O'
_chemical_formula_sum            'C15 H27 N2 O3'
_chemical_formula_weight         283.39
_chemical_melting_point          407
_chemical_name_systematic
; 
 14-Carbamoyl-7-azadispiro[5.1.5.2]pentadecane-7-oxyl 
 monohydrate 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 103.759(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6265(3)
_cell_length_b                   20.2553(9)
_cell_length_c                   11.5994(5)
_cell_measurement_reflns_used    9818
_cell_measurement_temperature    149(2)
_cell_measurement_theta_max      28.37
_cell_measurement_theta_min      2.70
_cell_volume                     1512.22(12)
_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      149(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17347
_diffrn_reflns_theta_full        28.38
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9703
_exptl_absorpt_correction_T_min  0.8562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       prism
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       0.021(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   1.127
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3743
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0733P)^2^+0.2919P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1232
_reflns_number_gt                3335
_reflns_number_total             3743
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301235j_si_001_2.cif
_cod_data_source_block           compound13_s5901
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               4027515