A crystalline C5-protonated 1,3-imidazol-4-ylidene.
Rottschäfer, Dennis; Glodde, Timo; Neumann, Beate; Stammler, Hans-Georg; Ghadwal, Rajendra S.; Chemical communications (Cambridge, England) 56 (2020) 2027–2030; doi:10.1039/c9cc09428h

data_1557044
_publ_section_title
;
 A crystalline C5-protonated 1,3-imidazol-4-ylidene.
;
_journal_issue                   13
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2027
_journal_page_last               2030
_journal_paper_doi               10.1039/c9cc09428h
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C39 H44 N2, 0.5[C7H8]'
_chemical_formula_sum            'C39 H44 N2'
_chemical_formula_weight         540.76
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-28
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2019-08-14 deposited with the CCDC.	2020-01-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   38.4682(4)
_cell_length_b                   38.4682(4)
_cell_length_c                   9.5772(2)
_cell_measurement_reflns_used    28455
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.2980
_cell_measurement_theta_min      3.2390
_cell_volume                     14172.4(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_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    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3114
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.983
_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    -92.00  -2.00   1.00   11.00    --  -38.50 125.00-150.00   90
  2  \w    -69.00  33.00   1.00   11.00    --  -38.50  77.00 120.00  102
  3  \w    -59.00  33.00   1.00   11.00    --  -38.50  38.00-120.00   92
  4  \w     13.00 114.00   1.00   11.00    --   43.07  77.00  60.00  101
  5  \w     13.00 114.00   1.00   11.00    --   43.07  77.00 -90.00  101
  6  \w     10.00 120.00   1.00   11.00    --   43.07  19.00 -60.00  110
  7  \w    -25.00  68.00   1.00   11.00    --   43.07 -57.00 -30.00   93
  8  \w     13.00 114.00   1.00   11.00    --   43.07  77.00   0.00  101
  9  \w     18.00 111.00   1.00   11.00    --   43.07  57.00 -90.00   93
 10  \w     13.00 114.00   1.00   11.00    --   43.07  77.00 -60.00  101
 11  \w     13.00 114.00   1.00   11.00    --   43.07  77.00-180.00  101
 12  \w     22.00 114.00   1.00   11.00    --   43.07  38.00  90.00   92
 13  \w     13.00 114.00   1.00   11.00    --   43.07  77.00 120.00  101
 14  \w     22.00 114.00   1.00   11.00    --   43.07  38.00-150.00   92
 15  \w     31.00 110.00   1.00   44.00    --  111.00 -94.00 -60.00   79
 16  \w     81.00 178.00   1.00   44.00    --  111.00  76.00 109.51   97
 17  \w     83.00 178.00   1.00   44.00    --  111.00  67.00 -81.62   95
 18  \w     82.00 178.00   1.00   44.00    --  111.00  73.00 177.30   96
 19  \w     43.00 137.00   1.00   44.00    --  111.00 -61.00 -30.00   94
 20  \w    138.00 173.00   1.00   44.00    --  111.00  77.00 -60.00   35
 21  \w    111.00 135.00   1.00   44.00    --  111.00  77.00 -30.00   24
;
_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      -0.0289144000
_diffrn_orient_matrix_UB_12      -0.0273616000
_diffrn_orient_matrix_UB_13      0.0170667000
_diffrn_orient_matrix_UB_21      0.0078266000
_diffrn_orient_matrix_UB_22      -0.0021738000
_diffrn_orient_matrix_UB_23      0.1575157000
_diffrn_orient_matrix_UB_31      -0.0265459000
_diffrn_orient_matrix_UB_32      0.0291811000
_diffrn_orient_matrix_UB_33      0.0278398000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            72087
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.516
_diffrn_reflns_theta_min         3.249
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.438
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.457
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
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 light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.014
_exptl_crystal_description       needle
_exptl_crystal_F_000             4672
_exptl_crystal_size_max          0.476
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.000064(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         7319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0394P)^2^+11.2405P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1068
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6284
_reflns_number_total             7319
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc09428h2.cif
_cod_data_source_block           compound2
_cod_depositor_comments
'Adding full bibliography for 1557041--1557044.cif.'
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               1557044
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C46 H52 N2'
_diffrn_oxdiff_digest_frames
;
01af2158d768f8e9dc024ce56a7ba829c8019661858
;
_diffrn_oxdiff_digest_hkl
;
01ee77bcfa17837642c7f3b63092e6c4951c33
;
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     43.79
_olex2_refinement_description
;
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              4989
_shelx_fab_checksum              24672
_olex2_date_sample_data_collection 2019-06-27
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.309
_oxdiff_exptl_absorpt_empirical_full_min 0.365