Air-persistent monomeric (amino)(carboxy) radicals derived from cyclic (alkyl)(amino) carbenes.
Mahoney, Janell K.; Martin, David; Thomas, Fabrice; Moore, Curtis E.; Rheingold, Arnold L.; Bertrand, Guy; Journal of the American Chemical Society 137 (2015) 7519–7525; doi:10.1021/jacs.5b04414

data_4129439
_publ_section_title
;
 Air-persistent monomeric (amino)(carboxy) radicals derived from cyclic
 (alkyl)(amino) carbenes.
;
_journal_issue                   23
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7519
_journal_page_last               7525
_journal_paper_doi               10.1021/jacs.5b04414
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C41 H62 N2 O, B F4'
_chemical_formula_sum            'C41 H62 B F4 N2 O'
_chemical_formula_weight         685.73
_chemical_name_systematic        'Radical 4e'
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-03-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.341(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.1080(11)
_cell_length_b                   14.0937(8)
_cell_length_c                   16.0726(11)
_cell_measurement_reflns_used    6158
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.71
_cell_measurement_theta_min      2.64
_cell_volume                     3785.8(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 APEX Cu'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.0914
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10098
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         68.282
_diffrn_reflns_theta_min         2.644
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker FR-591'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_max  0.320069
_exptl_absorpt_correction_T_min  0.204739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1134 before and 0.0364 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1174 before and 0.0383 after correction.
 The Ratio of minimum to maximum transmission is 0.64.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 31491 reflections, Rint = 0.0761
 (8831 with I > 3sig(I), Rint = 0.0452)
;
_exptl_crystal_colour            'clear dark blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_description       block
_exptl_crystal_F_000             1484
_exptl_crystal_recrystallization_method
'diffusion of dichloromethane and ether'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     513
_refine_ls_number_reflns         10098
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1284
_refine_ls_R_factor_gt           0.0744
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1019P)^2^+0.6721P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1843
_refine_ls_wR_factor_ref         0.2194
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6232
_reflns_number_total             10098
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b04414_si_004.cif
_cod_data_source_block           radical.3e
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4129439
_shelx_estimated_absorpt_t_max   0.876
_shelx_estimated_absorpt_t_min   0.823
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.570(2) 0.430(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Others
 1*[Sof(F6)]+1*[Sof(F4)]+1*[Sof(F8)]+1*[Sof(F3)]+1*[Sof(F5)]+1*[Sof(F7)]+1*
 [Sof(F9)]+1*[Sof(F1)]+1*[Sof(F2)]=4 with esd of 0.000001
4.a Ternary CH refined with riding coordinates:
 C17(H17), C20(H20), C36(H36), C39(H39)
4.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C24(H24A,H24B)
4.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C32(H32), C33(H33), C34(H34)
4.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C),
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,
 H29B,H29C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C40(H40A,H40B,H40C),
 C41(H41A,H41B,H41C)
;
_shelx_res_checksum              7825
_shelx_hkl_checksum              33595
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_completion    2014-04-02
_olex2_date_sample_data_collection 2014-04-01
_olex2_submission_original_sample_id 'Radical 4e'
_olex2_submission_special_instructions 'No special instructions were received'