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_4129442
_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         'C H2 Cl2, C41 H63 N2 O, B F4'
_chemical_formula_sum            'C42 H65 B Cl2 F4 N2 O'
_chemical_formula_weight         771.67
_chemical_name_systematic        'Iminium tetrafluoroborate 9'
_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             2015-04-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.487(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3686(5)
_cell_length_b                   10.8693(5)
_cell_length_c                   31.8290(12)
_cell_measurement_reflns_used    3526
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.93
_cell_measurement_theta_min      4.31
_cell_volume                     4207.6(3)
_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, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX CCD'
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            31283
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         68.866
_diffrn_reflns_theta_min         2.824
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker FR-591'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.805
_exptl_absorpt_correction_T_max  0.1671
_exptl_absorpt_correction_T_min  0.0634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1140 before and 0.0495 after correction.
The Ratio of minimum to maximum transmission is 0.3794.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear dark green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_description       needle
_exptl_crystal_F_000             1656
_exptl_crystal_recrystallization_method
'crystallized by diffusion of ether and dichloromethane'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.612
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     526
_refine_ls_number_reflns         7582
_refine_ls_number_restraints     64
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0704
_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^)+(0.1157P)^2^+2.3150P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1942
_refine_ls_wR_factor_ref         0.2148
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5439
_reflns_number_total             7582
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b04414_si_005.cif
_cod_data_source_block           iminium.5
_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               4129442
_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, All O(H) groups
2. Restrained distances
 F6-B2 = F7-B2 = F8-B2 = F5-B2
 1.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(B1) = Uanis(B2)
4. Rigid body (RIGU) restrains
 B1, F4, F3, F2, F1, F5, B2, F8, F6, F7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(F5)=Sof(F8)=Sof(F6)=Sof(F7)=Sof(B2)=1-FVAR(1)
 Sof(B1)=Sof(F4)=Sof(F3)=Sof(F2)=Sof(F1)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C18(H18), C15(H15), C35(H35), C38(H38)
6.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C3(H3A,H3B), C41(H41A,H41B)
6.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C12(H12), C11(H11), C32(H32), C31(H31), C33(H33)
6.d Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C19(H19A,H19B,H19C), C25(H25A,H25B,H25C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C), C27(H27A,H27B,H27C), C7(H7A,H7B,H7C), C20(H20A,
 H20B,H20C), C26(H26A,H26B,H26C), C6(H6A,H6B,H6C), C37(H37A,H37B,H37C),
 C40(H40A,H40B,H40C), C8(H8A,H8B,H8C), C5(H5A,H5B,H5C), C28(H28A,H28B,H28C),
 C36(H36A,H36B,H36C)
6.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              29912
_shelx_hkl_checksum              82271
_shelx_shelxl_version_number     2014/7
_olex2_submission_original_sample_id 4f
_olex2_submission_special_instructions 'No special instructions were received'