Synthesis and Electron Spin Relaxation of Tetracarboxylate Pyrroline Nitroxides.
Huang, Shengdian; Paletta, Joseph T.; Elajaili, Hanan; Huber, Kirby; Pink, Maren; Rajca, Suchada; Eaton, Gareth R.; Eaton, Sandra S.; Rajca, Andrzej; The Journal of organic chemistry 82 (2017) 1538–1544; doi:10.1021/acs.joc.6b02737

data_4032135
_publ_section_title
;
 Synthesis and Electron Spin Relaxation of Tetracarboxylate Pyrroline
 Nitroxides.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1538
_journal_page_last               1544
_journal_paper_doi               10.1021/acs.joc.6b02737
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C12 H14 N O9'
_chemical_formula_sum            'C12 H14 N O9'
_chemical_formula_weight         316.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
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_cell_angle_beta                 105.489(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1787(15)
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_cell_length_c                   11.6365(10)
_cell_measurement_reflns_used    9945
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.61
_cell_volume                     1432.5(2)
_computing_cell_refinement       'Bruker SAINT'
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_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 0.83
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23212
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.451
_diffrn_reflns_theta_min         1.306
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, G. Sheldrick; 2014'
_exptl_crystal_colour            colorless
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_exptl_crystal_description       block
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_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0412P)^2^+0.6339P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0865
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2524
_reflns_number_total             2949
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02737_si_001.cif
_cod_data_source_block           15131
_cod_depositor_comments          'Adding full bibliography for 4032135.cif.'
_cod_database_code               4032135
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.969
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              75771
_shelx_hkl_checksum              57091