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_4032315
_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         'C14 H18 N O9'
_chemical_formula_sum            'C14 H18 N O9'
_chemical_formula_weight         344.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 97.9090(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.3051(7)
_cell_length_b                   6.5192(3)
_cell_length_c                   15.4278(6)
_cell_measurement_reflns_used    5581
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      16.85
_cell_measurement_theta_min      2.43
_cell_volume                     1624.32(12)
_computing_cell_refinement       'APEX II v2014.11-0 (Bruker, 2014)'
_computing_data_collection       'APEX II v2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'APEX II v2014.11-0 (Bruker, 2014)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2013)'
_computing_publication_material  'SHELXTL (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELX (Bruker, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 83.33
_diffrn_detector_type            'Bruker APEXII'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
'0.5 degree frames measured for 0.3 seconds each'
_diffrn_measurement_device       'three-circle goniometer with fixed chi'
_diffrn_measurement_device_type  'Bruker Platform goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'silicon  1 1 1 and 3 1 1'
_diffrn_radiation_source         synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.41328
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13679
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        14.357
_diffrn_reflns_theta_max         16.916
_diffrn_reflns_theta_min         1.550
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.7441
_exptl_absorpt_correction_T_min  0.6260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, G. Sheldrick; 2014'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       block
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.115
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.699
_refine_diff_density_rms         0.225
_refine_ls_extinction_coef       0.35(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.230
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         2333
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.230
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0494
_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^)+(0.0827P)^2^+0.2655P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1273
_refine_ls_wR_factor_ref         0.1513
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1988
_reflns_number_total             2333
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02737_si_002.cif
_cod_data_source_block           s16003
_cod_database_code               4032315
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.992
_shelx_estimated_absorpt_t_max   0.996
_shelx_res_checksum              20079
_shelx_hkl_checksum              2101