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_4129441
_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         'C30 H35 F5 N O, C7 H8'
_chemical_formula_sum            'C37 H43 F5 N O'
_chemical_formula_weight         612.72
_chemical_name_systematic        4d
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.875(4)
_cell_length_b                   8.1455(13)
_cell_length_c                   18.299(3)
_cell_measurement_reflns_used    3681
_cell_measurement_temperature    100
_cell_measurement_theta_max      20.83
_cell_measurement_theta_min      2.50
_cell_volume                     3260.6(10)
_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_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21716
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.380
_diffrn_reflns_theta_min         2.169
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.0932
_exptl_absorpt_correction_T_min  0.0623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1076 before and 0.0581 after correction.
The Ratio of minimum to maximum transmission is 0.6685.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       block
_exptl_crystal_F_000             1300
_exptl_crystal_recrystallization_method
'crystallized from cooled toluene solution'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1824 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         6570
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0352P)^2^+0.0326P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0911
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                4943
_reflns_number_total             6570
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b04414_si_002.cif
_cod_data_source_block           radical.3c
_cod_original_cell_volume        3260.6(9)
_cod_database_code               4129441
_olex2_refinement_description
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C23(H23), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C9(H9A,H9B), C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B), C7(H7A,
 H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C16(H16), C17(H17), C34(H34), C33(H33), C37(H37), C35(H35), C36(H36)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C12(H12A,H12B,H12C), C22(H22A,H22B,H22C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C), C21(H21A,H21B,H21C), C38(H38A,H38B,H38C)
;
_shelx_res_checksum              85047
_shelx_hkl_checksum              43214
_shelx_shelxl_version_number     2014/7
_olex2_submission_original_sample_id 4d
_olex2_submission_special_instructions 'No special instructions were received'