Kekulé diradicaloids derived from a classical N-heterocyclic carbene.
Rottschäfer, Dennis; Neumann, Beate; Stammler, Hans-Georg; Andrada, Diego M.; Ghadwal, Rajendra S.; Chemical science 9 (2018) 4970–4976; doi:10.1039/c8sc01209a

data_1549301
_publ_section_title
;
 Kekul\'e diradicaloids derived from a classical N-heterocyclic carbene.
;
_journal_issue                   22
_journal_name_full               'Chemical science'
_journal_page_first              4970
_journal_page_last               4976
_journal_paper_doi               10.1039/c8sc01209a
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C60 H80 N4'
_chemical_formula_sum            'C60 H80 N4'
_chemical_formula_weight         857.28
_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
_audit_creation_date             2017-11-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-02-28 deposited with the CCDC.
2018-04-23 downloaded from the CCDC.
;
_cell_angle_alpha                97.968(3)
_cell_angle_beta                 90.283(3)
_cell_angle_gamma                110.092(4)
_cell_formula_units_Z            2
_cell_length_a                   10.4185(5)
_cell_length_b                   10.5244(5)
_cell_length_c                   25.1966(7)
_cell_measurement_reflns_used    13860
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.3920
_cell_measurement_theta_min      4.5030
_cell_volume                     2565.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.15e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.15e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.15e (Rigaku OD, 2015)'
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3114
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     21.00  84.00   1.00   10.57    --    0.00  57.00 150.00   63
  2  \w    -91.00 -58.00   1.00   10.57    --    0.00 -77.00-180.00   33
  3  \w     18.00  69.00   1.00   10.57    --    0.00  57.00 -90.00   51
  4  \w    -33.00  13.00   1.00   10.57    --    0.00  57.00 -90.00   46
  5  \w    -16.00  45.00   1.00   10.57    --    0.00  57.00   0.00   61
  6  \w    -47.00  35.00   1.00   10.57    --    0.00 -77.00-180.00   82
  7  \w    -37.00   5.00   1.00   10.57    --    0.00  57.00 150.00   42
  8  \w    -57.00 -20.00   1.00   42.28    --  -59.50 -77.00  60.00   37
  9  \w    -60.00 -20.00   1.00   42.28    --  -59.50 -77.00 -90.00   40
 10  \w   -147.00 -20.00   1.00   42.28    --  -59.50 -77.00   0.00  127
 11  \w   -151.00 -21.00   1.00   42.28    --  -59.50 -77.00 120.00  130
 12  \w   -130.00 -51.00   1.00   42.28    --  -59.50 -77.00 -60.00   79
 13  \w   -112.00 -62.00   1.00   42.28    --  -59.50 -77.00  60.00   50
 14  \w   -121.00 -57.00   1.00   42.28    --  -59.50 -77.00 150.00   64
 15  \w    -47.00 -20.00   1.00   42.28    --  -59.50 -77.00 -60.00   27
 16  \w    -94.00 -11.00   1.00   42.28    --  -59.50 125.00   0.00   83
 17  \w    -89.00  -2.00   1.00   42.28    --  -59.50 125.00 150.00   87
 18  \w    -48.00 -20.00   1.00   42.28    --  -59.50 -77.00-180.00   28
 19  \w   -101.00 -20.00   1.00   42.28    --  -59.50 -77.00  30.00   81
 20  \w    -59.00 -20.00   1.00   42.28    --  -59.50 -77.00  90.00   39
 21  \w   -150.00 -58.00   1.00   42.28    --  -59.50 -77.00-150.00   92
 22  \w    -56.00 -20.00   1.00   42.28    --  -59.50 -77.00 150.00   36
 23  \w    -54.00 -20.00   1.00   42.28    --  -59.50 -77.00-150.00   34
 24  \w   -129.00 -72.00   1.00   42.28    --  -59.50 -77.00 -90.00   57
 25  \w     23.00  68.00   1.00   42.28    --   59.50-125.00 150.00   45
 26  \w    110.00 143.00   1.00   42.28    --   59.50 125.00 120.00   33
 27  \w    108.00 139.00   1.00   42.28    --   59.50 125.00  30.00   31
 28  \w     90.00 122.00   1.00   42.28    --   59.50-125.00 150.00   32
 29  \w     94.00 143.00   1.00   42.28    --   59.50 125.00  60.00   49
 30  \w     82.00 108.00   1.00    5.00    --  119.00  63.00   0.00   26
 31  \w     82.00 110.00   1.00    5.00    --  119.00  63.00-120.00   28
 32  \w     34.00 113.00   1.00    5.00    --  119.00-111.00 -30.00   79
 33  \w     82.00 170.00   1.00    5.00    --  119.00  63.00  90.00   88
 34  \w     81.00 177.00   1.00    5.00    --  119.00  77.00 120.00   96
 35  \w     80.00 178.00   1.00    5.00    --  119.00  77.00 -30.00   98
 36  \w     81.00 126.00   1.00    5.00    --  119.00  66.00  35.68   45
 37  \w     80.00 177.00   1.00    5.00    --  119.00  77.00   0.00   97
 38  \w     80.00 178.00   1.00    5.00    --  119.00  77.00 -60.00   98
 39  \w     33.00 116.00   1.00    5.00    --  119.00-111.00 150.00   83
 40  \w     80.00 107.00   1.00    5.00    --  119.00  77.00  30.00   27
 41  \w    110.00 176.00   1.00    5.00    --  119.00  77.00 150.00   66
 42  \w     82.00 109.00   1.00    5.00    --  119.00  63.00 -60.00   27
 43  \w     81.00 109.00   1.00    5.00    --  119.00  66.00-137.16   28
 44  \w     83.00 111.00   1.00    5.00    --  119.00  56.00-129.64   28
 45  \w     80.00 107.00   1.00    5.00    --  119.00  77.00 150.00   27
 46  \w     82.00 109.00   1.00    5.00    --  119.00  63.00 -30.00   27
 47  \w     83.00 110.00   1.00    5.00    --  119.00  50.00-150.00   27
 48  \w     83.00 109.00   1.00    5.00    --  119.00  63.00 -90.00   26
 49  \w     81.00 107.00   1.00    5.00    --  119.00  77.00 -90.00   26
 50  \w     82.00 109.00   1.00    5.00    --  119.00  63.00  30.00   27
 51  \w     30.00 158.00   1.00    5.00    --  119.00 -77.00 -30.00  128
 52  \w     84.00 111.00   1.00    5.00    --  119.00  63.00-180.00   27
 53  \w     80.00 178.00   1.00    5.00    --  119.00  77.00-180.00   98
 54  \w     83.00 114.00   1.00    5.00    --  119.00  50.00  90.00   31
 55  \w     82.00 109.00   1.00    5.00    --  119.00  63.00 150.00   27
 56  \w     83.00 108.00   1.00    5.00    --  119.00  63.00 120.00   25
 57  \w    117.00 176.00   1.00    5.00    --  119.00  63.00-150.00   59
 58  \w     43.00 157.00   1.00    5.00    --  119.00 -77.00 150.00  114
 59  \w     82.00 109.00   1.00    5.00    --  119.00  59.00 112.11   27
 60  \w     82.00 110.00   1.00    5.00    --  119.00  63.00-150.00   28
 61  \w     64.00 115.00   1.00    5.00    --  119.00-111.00-120.00   51
 62  \w     90.00 115.00   1.00    5.00    --  119.00-111.00  60.00   25
 63  \w     82.00 161.00   1.00    5.00    --  119.00  63.00  60.00   79
 64  \w     80.00 155.00   1.00    5.00    --  119.00  77.00-120.00   75
 65  \w     54.00  81.00   1.00    5.00    --  119.00-111.00  60.00   27
 66  \w    128.00 163.00   1.00    5.00    --  119.00  66.00  35.68   35
 67  \w     82.00 107.00   1.00    5.00    --  119.00  66.00 126.96   25
 68  \w     82.00 109.00   1.00    5.00    --  119.00  60.00 178.42   27
 69  \w     83.00 175.00   1.00    5.00    --  119.00  60.00 -80.22   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1008393000
_diffrn_orient_matrix_UB_12      0.0008290000
_diffrn_orient_matrix_UB_13      -0.0447645000
_diffrn_orient_matrix_UB_21      0.0839591000
_diffrn_orient_matrix_UB_22      0.1510127000
_diffrn_orient_matrix_UB_23      -0.0028516000
_diffrn_orient_matrix_UB_31      0.0874787000
_diffrn_orient_matrix_UB_32      -0.0452060000
_diffrn_orient_matrix_UB_33      -0.0425649000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            37630
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.128
_diffrn_reflns_theta_min         3.548
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.479
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.762
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.15e (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.110
_exptl_crystal_description       rhomb
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.037
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     593
_refine_ls_number_reflns         9804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0716
_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^)+(0.1194P)^2^+1.8830P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2049
_refine_ls_wR_factor_ref         0.2208
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7686
_reflns_number_total             9804
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc01209a2.cif
_cod_data_source_block           rottschaefer54
_cod_depositor_comments
'Adding full bibliography for 1549300--1549303.cif.'
_cod_original_cell_volume        2565.45(19)
_cod_database_code               1549301
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C60 H80 N4'
_reflns_odcompleteness_completeness 97.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C22(H22), C25(H25), C40(H40), C43(H43), C52(H52), C55(H55)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C32(H32A,H32B), C33(H33A,H33B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20), C29(H29), C30(H30),
 C36(H36), C37(H37), C38(H38), C48(H48), C49(H49), C50(H50), C59(H59), C60(H60)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C44(H44A,H44B,H44C),
 C45(H45A,H45B,H45C), C53(H53A,H53B,H53C), C54(H54A,H54B,H54C), C56(H56A,H56B,
 H56C), C57(H57A,H57B,H57C)
;
_shelx_res_checksum              54411
_olex2_date_sample_data_collection 2017-11-15
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.534
_oxdiff_exptl_absorpt_empirical_full_min 0.728