Oxygen atom transfer: A mild and efficient method for generating iminyl radicals
Kim, Youngsuk; Bielawski, Christopher W.; Lee, Eunsung; Chemical Communications  (2019) –; doi:10.1039/C9CC03521D

data_7123505
_publ_section_title
;
 Oxygen atom transfer: A mild and efficient method for generating iminyl
 radicals
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC03521D
_journal_year                    2019
_chemical_formula_moiety         'C27 H36 N3 O0.5'
_chemical_formula_sum            'C27 H36 N3 O0.5'
_chemical_formula_weight         410.59
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-05-30
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2019-03-26 deposited with the CCDC.    2019-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.55(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.496(5)
_cell_length_b                   5.6560(11)
_cell_length_c                   19.914(4)
_cell_measurement_reflns_used    33155
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.539
_cell_measurement_theta_min      2.795
_cell_volume                     2444.1(10)
_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
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  PAL_2D
_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  0.0331
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            20101
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         29.539
_diffrn_reflns_theta_min         2.795
_diffrn_source                   'PLSII 2D bending magnet'
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.116
_exptl_crystal_description       plate
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         6816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0627
_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^)+(0.0931P)^2^+0.5500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1700
_refine_ls_wR_factor_ref         0.1750
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6005
_reflns_number_total             6816
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc03521d2.cif
_cod_data_source_block           p21c
_cod_original_formula_sum        'C27 H36 N3 O0.50'
_cod_database_code               7123505
_shelx_shelxl_version_number     2014/7
_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: H009(0.5) H00A(0.5) C00E(0.5) C00F(0.5) H00E(0.5) H00F(0.5)
 H00G(0.5) C00H(0.5) H00K(0.5) C00K(0.5) H00O(0.5) N00L(0.5) C00P(0.5)
 H00V(0.5) C00Q(0.5) N00R(0.5) C00S(0.5) C00T(0.5) C00U(0.5) H00W(0.5)
 C00X(0.5) H00X(0.5) C00Z(0.5) H00Y(0.5) H(0.5) HA(0.5) C010(0.5) H01A(0.5)
 H01B(0.5) H01C(0.5) C011(0.5) H01D(0.5) H01E(0.5) H01F(0.5) C00R(0.5)
 C00Y(0.5) H00Z(0.5) C0(0.5) H0A(0.5) H0B(0.5) H0C(0.5) C00{(0.5) H00(0.5)
 HB(0.5) HC(0.5) N1(0.5) C00V(0.5) H0AA(0.5) C0AA(0.5) H0AB(0.5) C1AA(0.5)
 C2AA(0.5) H2AA(0.5) C1(0.5) H1A(0.5) H1B(0.5) H1C(0.5) C00L(0.5) H1AA(0.5)
 C3AA(0.5) H3AA(0.5) H3AB(0.5) H3AC(0.5) O1(0.5) N2(0.5)
3.a Ternary CH refined with riding coordinates:
 C009(H009), C00A(H00B), C00C(H00D), C00K(H00O), C00X(H00X), C00Y(H00Z),
 C00L(H1AA)
3.b Aromatic/amide H refined with riding coordinates:
 C004(H004), C006(H006), C008(H008), C009(H00A), C00B(H00C), C00H(H00K),
 C00P(H00V), C00U(H00W), C00V(H0AA), C0AA(H0AB), C2AA(H2AA)
3.c Idealised Me refined as rotating group:
 C00F(H00E,H00F,H00G), C00G(H00H,H00I,H00J), C00I(H00L,H00M,H00N), C00N(H00P,
 H00Q,H00R), C00O(H00S,H00T,H00U), C00Z(H00Y,H,HA), C010(H01A,H01B,H01C),
 C011(H01D,H01E,H01F), C0(H0A,H0B,H0C), C00{(H00,HB,HC), C1(H1A,H1B,H1C),
 C3AA(H3AA,H3AB,H3AC)
;
_olex2_submission_special_instructions 'No special instructions were received'