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_4129440
_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         'C27 H35 F7 N O'
_chemical_formula_sum            'C27 H35 F7 N O'
_chemical_formula_weight         522.56
_chemical_name_systematic        4b
_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
_atom_sites_solution_primary     direct
_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                 90.095(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8071(4)
_cell_length_b                   24.8008(12)
_cell_length_c                   11.5922(5)
_cell_measurement_reflns_used    5444
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.58
_cell_measurement_theta_min      2.41
_cell_volume                     2532.0(2)
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19172
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         1.757
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.0998
_exptl_absorpt_correction_T_min  0.0644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1550 before and 0.0426 after correction. The Ratio of minimum to maximum transmission is 0.6453. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       block
_exptl_crystal_F_000             1100
_exptl_crystal_recrystallization_method
'crystallized from a cooled hexane solution'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.737
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         4920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0669
_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^)+(0.0988P)^2^+3.5088P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1821
_refine_ls_wR_factor_ref         0.1923
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4070
_reflns_number_total             4920
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b04414_si_003.cif
_cod_data_source_block           radical.3d
_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               4129440
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9979(4) 0.0021(4)
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.a Ternary CH refined with riding coordinates:
 C23(H23), C20(H20)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C5(H5A,H5B), C11(H11A,H11B), C10(H10A,H10B), C8(H8A,H8B), C9(H9A,
 H9B)
3.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C16(H16)
3.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C12(H12A,H12B,H12C), C24(H24A,H24B,H24C), C13(H13A,H13B,
 H13C), C25(H25A,H25B,H25C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              62665
_shelx_hkl_checksum              97480
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 11/14/14
_olex2_submission_original_sample_id 4b
_olex2_submission_special_instructions 'No special instructions were received'