Synthesis and stability of cyclic α-hydrogen nitroxides.
Toledo, Hila; Amar, Michal; Bar, Sukanta; Iron, Mark A.; Fridman, Natalia; Tumanskii, Boris; Shimon, Linda J. W.; Botoshansky, Mark; Szpilman, Alex M.; Organic & biomolecular chemistry 13 (2015) 10726–10733; doi:10.1039/c5ob01443c

data_7154669
_publ_section_title
;
 Synthesis and stability of cyclic \a-hydrogen nitroxides.
;
_journal_issue                   43
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10726
_journal_page_last               10733
_journal_paper_doi               10.1039/c5ob01443c
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H19 N O4'
_chemical_formula_sum            'C18 H19 N O4'
_chemical_formula_weight         313.34
_chemical_name_common            Szpilman12
_chemical_name_systematic
'methyl 3-isopropyl-1-methyl-4,9-dioxo-2,3,4,9-tetrahydro-1H-benzo[f]isoindole-1-carboxylate'
_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_block_doi                 10.5517/cc1jbpg0
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-07-03 deposited with the CCDC.
2015-08-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 106.742(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.5180(4)
_cell_length_b                   12.3210(5)
_cell_length_c                   9.0570(8)
_cell_measurement_reflns_used    2479
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.14
_cell_measurement_theta_min      1.37
_cell_volume                     1658.27(17)
_computing_cell_refinement       'DENZO HKL2000 (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius, 2006)'
_computing_data_reduction        'DENZO HKL2000 (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Mercury 3.5'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 95
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi- and omega-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  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2438
_diffrn_reflns_theta_full        24.14
_diffrn_reflns_theta_max         24.14
_diffrn_reflns_theta_min         1.37
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_correction_T_min  0.9838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'  
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0759P)^2^+0.3575P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1301
_reflns_number_gt                2020
_reflns_number_total             2438
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01443c2.cif
_cod_data_source_block           Szpilman12
_cod_depositor_comments
'Adding full bibliography for 7154666--7154672.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7154669