New Face of Phenalenyl Based Radical in Transition Metal Free C-H Arylation of Heteroarenes at Room Temperature: Trapping the Radical Initiator via C-C σ Bond Formation
Mandal, Swadhin K.; Ahmed, Jasimuddin; P, Sreejyothi; Vijaykumar, Gonela; Jose, Anex; Raj, Manthan; Chem. Sci.  (2017) –; doi:10.1039/C7SC02661G

data_1547135
_publ_section_title
;
 New Face of Phenalenyl Based Radical in Transition Metal Free C-H
 Arylation of Heteroarenes at Room Temperature: Trapping the Radical
 Initiator via C-C \s Bond Formation
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC02661G
_journal_year                    2017
_chemical_formula_moiety         'C28 H37 K N2 O7, C2 H3 N'
_chemical_formula_sum            'C30 H40 K N3 O7'
_chemical_formula_weight         593.75
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-12-04
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2016-12-05 deposited with the CCDC.
2017-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                71.592(5)
_cell_angle_beta                 86.228(5)
_cell_angle_gamma                78.678(5)
_cell_formula_units_Z            4
_cell_length_a                   12.0598(7)
_cell_length_b                   16.2046(10)
_cell_length_c                   17.0517(10)
_cell_measurement_reflns_used    2721
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      26.2130
_cell_measurement_theta_min      1.6890
_cell_volume                     3100.3(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9507
_diffrn_measured_fraction_theta_max 0.9510
_diffrn_measurement_details
;
  1 omega  -20.00   30.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.7617  -99.0000  -90.0000 50

  2 omega  -50.00   66.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       27.1679  -57.0000   90.0000 116

  3 omega  -50.00   66.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       27.1679  -57.0000  -30.0000 116

  4 omega  -48.00   77.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       27.1679  -38.0000 -180.0000 125
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0289988000
_diffrn_orient_matrix_UB_12      0.0349506000
_diffrn_orient_matrix_UB_13      -0.0207345000
_diffrn_orient_matrix_UB_21      0.0213131000
_diffrn_orient_matrix_UB_22      -0.0221727000
_diffrn_orient_matrix_UB_23      -0.0292072000
_diffrn_orient_matrix_UB_31      -0.0479874000
_diffrn_orient_matrix_UB_32      0.0221533000
_diffrn_orient_matrix_UB_33      -0.0252789000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0895
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15934
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.72
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.878
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     743
_refine_ls_number_reflns         10826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1451
_refine_ls_R_factor_gt           0.0847
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0762P)^2^+5.9417P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1832
_refine_ls_wR_factor_ref         0.2190
_reflns_number_gt                6447
_reflns_number_total             10826
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7sc02661g2.cif
_cod_data_source_block           jm_k1_a
_cod_database_code               1547135
_chemical_oxdiff_formula         'C H N O K'
_reflns_odcompleteness_completeness 95.07
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C33(H33)
2.b Secondary CH2 refined with riding coordinates:
 C43(H43A,H43B), C24(H24A,H24B), C21(H21A,H21B), C13(H13A,H13B), C23(H23A,
 H23B), C19(H19A,H19B), C20(H20A,H20B), C42(H42A,H42B), C14(H14A,H14B),
 C40(H40A,H40B), C49(H49A,H49B), C16(H16A,H16B), C22(H22A,H22B), C15(H15A,H15B),
  C45(H45A,H45B), C41(H41A,H41B), C17(H17A,H17B), C48(H48A,H48B), C38(H38A,
 H38B), C44(H44A,H44B), C46(H46A,H46B), C47(H47A,H47B), C18(H18A,H18B),
 C39(H39A,H39B), C36(H36A,H36B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N4(H4A), C2(H2), C3(H3), C34(H34), C8(H8), C29(H29), C6(H6), C4(H4),
 C28(H28), C32(H32), C5(H5), C30(H30), C31(H31)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C51(H51A,H51B,H51C), C12(H12A,H12B,H12C), C50(H50A,H50B,
 H50C)
;
_olex2_submission_special_instructions 'No special instructions were received'