Synthesis and reduction kinetics of sterically shielded pyrrolidine nitroxides.
Paletta, Joseph T.; Pink, Maren; Foley, Bridget; Rajca, Suchada; Rajca, Andrzej; Organic letters 14 (2012) 5322–5325; doi:10.1021/ol302506f

data_1508699
_publ_section_title
;
 Synthesis and reduction kinetics of sterically shielded pyrrolidine
 nitroxides.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5322
_journal_page_last               5325
_journal_paper_doi               10.1021/ol302506f
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C15 H23 N1 O3'
_chemical_formula_sum            'C15 H23 N O3'
_chemical_formula_weight         265.35
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             12-09-05
_audit_creation_method           CRYSTALS_ver_14.40
_cell_angle_alpha                90
_cell_angle_beta                 92.4100(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0250(4)
_cell_length_b                   9.9052(5)
_cell_length_c                   8.9614(4)
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    150
_cell_measurement_theta_max      24
_cell_measurement_theta_min      3
_cell_volume                     711.70(6)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.824
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  'diamond 111'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.41238
_diffrn_reflns_av_R_equivalents  0.045
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17465
_diffrn_reflns_theta_full        17.925
_diffrn_reflns_theta_max         23.900
_diffrn_reflns_theta_min         1.320
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  1.00
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.55
_refine_diff_density_min         -0.47
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0709
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         4820
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0963
_refine_ls_shift/su_max          0.0066575
_refine_ls_shift/su_mean         0.0000958
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.79P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2912
_refine_ls_wR_factor_gt          0.2519
_refine_ls_wR_factor_ref         0.2618
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                4392
_reflns_number_total             4827
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.1017
_oxford_refine_ls_scale          1.71(2)
_oxford_reflns_number_all        4823
_oxford_reflns_threshold_expression_ref I>0.0\s(I)
_oxford_structure_analysis_title 'p21m in P2(1)/m'
_cod_data_source_file            ol302506f_si_002.cif
_cod_data_source_block           12507
_cod_original_sg_symbol_H-M      'P 1 21/m 1 '
_cod_original_formula_sum        'C15 H23 N1 O3'
_cod_database_code               1508699
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   ( 341,X'S) H   (3411,X'S) 
RIDE C   (   5,X'S) H   (  52,X'S) H   (  92,X'S) 
RIDE C   (   6,X'S) H   (  81,X'S) H   (  73,X'S) 
RIDE C   (   7,X'S) H   (  72,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  83,X'S) H   (  82,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  93,X'S) 
RIDE C   (  11,X'S) H   ( 153,X'S) H   (1541,X'S) 
RIDE C   (  12,X'S) H   ( 142,X'S) H   ( 144,X'S) 
RIDE C   (  13,X'S) H   ( 132,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 143,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 154,X'S) H   ( 157,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END
;