Triazenyl Radicals Stabilized by N-Heterocyclic Carbenes.
Back, Jisu; Park, Junbeom; Kim, Youngsuk; Kang, Haneol; Kim, Yonghwi; Park, Moon Jeong; Kim, Kimoon; Lee, Eunsung; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b08753

data_4126621
_publ_section_title
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 Triazenyl Radicals Stabilized by N-Heterocyclic Carbenes.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b08753
_journal_year                    2017
_chemical_formula_moiety         'C54 H73 N7'
_chemical_formula_sum            'C54 H73 N7'
_chemical_formula_weight         820.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.42(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.520(3)
_cell_length_b                   27.190(5)
_cell_length_c                   14.380(3)
_cell_measurement_reflns_used    31131
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      22.886
_cell_measurement_theta_min      2.031
_cell_volume                     4890.9(18)
_computing_cell_refinement       HKL3000
_computing_data_collection       'PAL ADSC Quantum-210 ADX Program'
_computing_data_reduction        HKL3000
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  'Si(111) double crystal monochromator'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_reflns_av_R_equivalents  0.1366
_diffrn_reflns_av_unetI/netI     0.1621
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25098
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        24.317
_diffrn_reflns_theta_max         24.317
_diffrn_reflns_theta_min         2.031
_diffrn_source                   'PLSII 2D bending magnet'
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light orange'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_description       block
_exptl_crystal_F_000             1784
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.874
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     619
_refine_ls_number_reflns         8240
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      0.872
_refine_ls_R_factor_all          0.1685
_refine_ls_R_factor_gt           0.0568
_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^)+(0.0618P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1484
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3585
_reflns_number_total             8240
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            4a.cif
_cod_data_source_block           p21n
_cod_original_cell_volume        4890.9(17)
_cod_database_code               4126621
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.997
_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. Uiso/Uaniso restraints and constraints
Uanis(C2A) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3A) \\sim Ueq, Uanis(C3)
\\sim Ueq, Uanis(C0AA) \\sim Ueq, Uanis(C0AB) \\sim Ueq, Uanis(C1AA) \\sim Ueq,
Uanis(C01J) \\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
3. Others
 Sof(C1AA)=Sof(H1AB)=Sof(C0AB)=Sof(H0AE)=Sof(H0AF)=Sof(H0AG)=Sof(C1A)=
 Sof(H1AC)=Sof(H1AD)=Sof(H1AE)=1-FVAR(1)
 Sof(C01J)=Sof(H01)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C0AA)=Sof(H0AB)=
 Sof(H0AC)=Sof(H0AD)=FVAR(1)
 Fixed Sof: H01M(0.7) H01N(0.3) C2(0.7) H2A(0.7) H2B(0.7) H2C(0.7) C3(0.7)
 H3A(0.7) H3B(0.7) H3C(0.7) C2A(0.3) H2AA(0.3) H2AB(0.3) H2AC(0.3) C3A(0.3)
 H3AA(0.3) H3AB(0.3) H3AC(0.3)
4.a Ternary CH refined with riding coordinates:
 C00K(H00K), C00L(H00L), C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011),
 C01C(H01M), C01C(H01N), C01J(H01), C1AA(H1AB)
4.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00F(H00F), C00M(H00M), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00T(H00T), C00V(H00V), C00W(H00W), C012(H012), C013(H013),
 C015(H015), C017(H017), C019(H019), C01D(H01O)
4.c Idealised Me refined as rotating group:
 C00X(H00A,H00B,H00C), C014(H01A,H01B,H01C), C018(H01D,H01E,H01F), C01A(H01G,
 H01H,H01I), C01B(H01J,H01K,H01L), C01E(H01P,H01Q,H01R), C01F(H01S,H01T,H01U),
 C01G(H01V,H01W,H01X), C01H(H01Y,H,HA), C01I(H01Z,HB,HC), C01K(H0AA,HD,HE),
 C01L(H1AA,HF,HG), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C2A(H2AA,H2AB,H2AC),
 C3A(H3AA,H3AB,H3AC), C1(H1A,H1B,H1C), C0AA(H0AB,H0AC,H0AD), C0AB(H0AE,H0AF,
 H0AG), C1A(H1AC,H1AD,H1AE)
;
_olex2_submission_special_instructions 'No special instructions were received'