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_1549300
_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, 2(I), 2(C H4 O)'
_chemical_formula_sum            'C62 H88 I2 N4 O2'
_chemical_formula_weight         1175.16
_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             2017-12-07
_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                90
_cell_angle_beta                 97.6225(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.01776(12)
_cell_length_b                   11.68842(10)
_cell_length_c                   18.61137(19)
_cell_measurement_reflns_used    68766
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      31.8190
_cell_measurement_theta_min      2.0570
_cell_volume                     3022.44(5)
_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      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0951
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -93.00   5.00   1.00    1.25    --  -23.50 -77.00   0.00   98
  2  \w      6.00  93.00   1.00    1.25    --   24.78  57.00  60.00   87
  3  \w      6.00  93.00   1.00    1.25    --   24.78  57.00-120.00   87
  4  \w    -20.00  65.00   1.00    1.25    --   24.78 -99.00-150.00   85
  5  \w      6.00  93.00   1.00    1.25    --   24.78  57.00 150.00   87
  6  \w    -44.00  43.00   1.00    1.25    --   24.78 -57.00  90.00   87
  7  \w      6.00  83.00   1.00    1.25    --   24.78-130.00  58.60   77
  8  \w     -4.00  94.00   1.00    1.25    --   24.78  77.00 -60.00   98
  9  \w    -44.00  43.00   1.00    1.25    --   24.78 -57.00   0.00   87
 10  \w    -44.00  43.00   1.00    1.25    --   24.78 -57.00 -90.00   87
 11  \w    -95.00  48.00   1.00    1.25    --  -23.50   0.00-180.00  143
 12  \w    -95.00  48.00   1.00    1.25    --  -23.50   0.00-150.00  143
 13  \w     -4.00  94.00   1.00    1.25    --   24.78  77.00-180.00   98
 14  \w      3.00  95.00   1.00    1.25    --   24.78  38.00 120.00   92
 15  \w      6.00  93.00   1.00    1.25    --   24.78  57.00 130.00   87
 16  \w      6.00  93.00   1.00    1.25    --   24.78  57.00   0.00   87
 17  \w    -20.00  65.00   1.00    1.25    --   24.78 -99.00  90.00   85
 18  \w    -10.00  72.00   1.00    1.25    --   24.78-111.00-111.39   82
 19  \w    -46.00  47.00   1.00    1.25    --   24.78 -38.00 150.00   93
 20  \w    -95.00  48.00   1.00    1.25    --  -23.50   0.00 -90.00  143
 21  \w    -95.00  48.00   1.00    1.25    --  -23.50   0.00 -60.00  143
 22  \w    -95.00  48.00   1.00    1.25    --  -23.50   0.00 -30.00  143
 23  \w    -95.00  48.00   1.00    1.25    --  -23.50   0.00-120.00  143
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0418293000
_diffrn_orient_matrix_UB_12      -0.0209447000
_diffrn_orient_matrix_UB_13      0.0132613000
_diffrn_orient_matrix_UB_21      -0.0003972000
_diffrn_orient_matrix_UB_22      0.0488355000
_diffrn_orient_matrix_UB_23      0.0225820000
_diffrn_orient_matrix_UB_31      -0.0292732000
_diffrn_orient_matrix_UB_32      0.0292949000
_diffrn_orient_matrix_UB_33      -0.0281546000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            171581
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.028
_diffrn_reflns_theta_min         1.714
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.083
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.307
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1220
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.308
_exptl_crystal_size_min          0.204
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         8848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0220
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0176P)^2^+1.7845P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0482
_refine_ls_wR_factor_ref         0.0499
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8020
_reflns_number_total             8848
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc01209a2.cif
_cod_data_source_block           rottschaefer61
_cod_depositor_comments
'Adding full bibliography for 1549300--1549303.cif.'
_cod_database_code               1549300
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C62 H88 I1 N4 O2'
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_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)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
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)
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), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              19999
_olex2_date_sample_data_collection 2017-12-06
_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 1.223
_oxdiff_exptl_absorpt_empirical_full_min 0.849