In search of a new class of stable nitroxide: synthesis and reactivity of a peri-substituted N,N-bissulfonylhydroxylamine.
Patel, Bhaven; Carlisle, Julie; Bottle, Steven E.; Hanson, Graeme R.; Kariuki, Benson M.; Male, Louise; McMurtrie, John C.; Spencer, Neil; Grainger, Richard S.; Organic & biomolecular chemistry 9 (2011) 2336–2344; doi:10.1039/c0ob00976h

data_7151789
_publ_section_title
;
 In search of a new class of stable nitroxide: synthesis and reactivity
 of a peri-substituted N,N-bissulfonylhydroxylamine.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2336
_journal_page_last               2344
_journal_paper_doi               10.1039/c0ob00976h
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C18 H19 N3 O5 S2'
_chemical_formula_sum            'C18 H19 N3 O5 S2'
_chemical_formula_weight         421.48
_chemical_name_common
;
(Z)-1,1,3,3-tetraoxidonaphtho(1,8-d,e)(1,3,2)dithiazin-2-yl N-
(2-cyanopropan-2-yl)isobutyimidate
;
_chemical_name_systematic
;
(Z)-1,1,3,3-tetraoxidonaphtho[1,8-d,e][1,3,2]dithiazin-2-yl
N-(2-cyanopropan-2-yl)isobutyimidate
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.420(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.1983(15)
_cell_length_b                   8.5889(7)
_cell_length_c                   15.6813(15)
_cell_measurement_reflns_used    5752
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.7402
_cell_measurement_theta_min      3.0690
_cell_volume                     2037.8(3)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.13 (release 29-11-2007 CrysAlis171 .NET)
(compiled Nov 29 2007,17:23:28)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.13 (release 29-11-2007 CrysAlis171 .NET)
(compiled Nov 29 2007,17:23:28)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.13 (release 29-11-2007 CrysAlis171 .NET)
(compiled Nov 29 2007,17:23:28)
;
_computing_molecular_graphics
;ORTEPIII (Farrugia, 1997)
WINGX-32 (Farrugia, 1999)
;
_computing_publication_material  'enCIFer 1.0 (CCDC, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, et. al. 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.0774
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14029
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.87
_diffrn_reflns_theta_min         3.08
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.87431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       multi-faced
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4719
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.6000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1069
_reflns_number_gt                3321
_reflns_number_total             4719
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob00976h.txt
_cod_data_source_block           9
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7151789