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_4126622
_publ_section_title
;
 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 H72 N7'
_chemical_formula_sum            'C54 H72 N7'
_chemical_formula_weight         819.18
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-05-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.77(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.821(3)
_cell_length_b                   28.197(6)
_cell_length_c                   13.549(3)
_cell_measurement_reflns_used    4522
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.726
_cell_measurement_theta_min      2.117
_cell_volume                     4887.6(19)
_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      100.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0609
_diffrn_reflns_av_unetI/netI     0.0872
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14382
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        23.726
_diffrn_reflns_theta_max         23.726
_diffrn_reflns_theta_min         2.117
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1780
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0148(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     587
_refine_ls_number_reflns         7769
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.933
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0559
_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^)+(0.0894P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1330
_refine_ls_wR_factor_ref         0.1570
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4522
_reflns_number_total             7769
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            3a.cif
_cod_data_source_block           p21n
_cod_original_cell_volume        4887.6(17)
_cod_database_code               4126622
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.987
_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. Others
 Fixed Sof: H18(0.6) H18A(0.4) C0AA(0.6) H0AA(0.6) H0AB(0.6) H0AC(0.6)
 C1AA(0.6) H1AA(0.6) H1AB(0.6) H1AC(0.6) C0AB(0.4) H0AD(0.4) H0AE(0.4)
 H0AF(0.4) C1AB(0.4) H1AD(0.4) H1AE(0.4) H1AF(0.4)
3.a Ternary CH refined with riding coordinates:
 C1(H1), C11(H11), C18(H18), C18(H18A), C25(H25), C30(H30), C39(H39), C44(H44),
  C52(H52)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C21(H21), C23(H23), C24(H24),
 C33(H33), C34(H34), C37(H37), C41(H41), C42(H42), C48(H48), C49(H49), C50(H50)
3.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C),
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C31(H31A,H31B,
 H31C), C38(H38A,H38B,H38C), C40(H40A,H40B,H40C), C43(H43A,H43B,H43C), C45(H45A,
 H45B,H45C), C53(H53A,H53B,H53C), C54(H54A,H54B,H54C), C0AA(H0AA,H0AB,H0AC),
 C1AA(H1AA,H1AB,H1AC), C0AB(H0AD,H0AE,H0AF), C1AB(H1AD,H1AE,H1AF)
;
_olex2_submission_special_instructions 'No special instructions were received'