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_1557043
_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 Au Cl N2, C7 H8'
_chemical_formula_sum            'C46 H52 Au Cl N2'
_chemical_formula_weight         865.31
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-05
_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                 93.6946(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2795(3)
_cell_length_b                   16.8120(3)
_cell_length_c                   19.2885(4)
_cell_measurement_reflns_used    26651
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.6540
_cell_measurement_theta_min      3.4540
_cell_volume                     3973.70(15)
_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    '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 0.990
_diffrn_measured_fraction_theta_max 0.961
_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    -69.00  33.00   1.00    3.00    --  -38.50  77.00-180.00  102
  2  \w    -59.00  33.00   1.00    3.00    --  -38.50  38.00 -60.00   92
  3  \w   -107.00 -13.00   1.00    3.00    --  -38.50 -57.00 -30.00   94
  4  \w   -124.00  47.00   1.00    3.00    --  -38.50   0.00 150.00  171
  5  \w   -116.00  -5.00   1.00    3.00    --  -38.50 -19.00 120.00  111
  6  \w   -110.00 -18.00   1.00    3.00    --  -38.50 -38.00  30.00   92
  7  \w     13.00 114.00   1.00    3.00    --   42.89  76.00 -99.00  101
  8  \w     13.00 114.00   1.00    3.00    --   42.89  77.00  30.00  101
  9  \w     13.00 114.00   1.00    3.00    --   42.89  77.00-180.00  101
 10  \w     23.00  97.00   1.00    3.00    --   42.89-125.00 120.00   74
 11  \w     23.00  97.00   1.00    3.00    --   42.89-125.00  60.00   74
 12  \w     13.00 114.00   1.00    3.00    --   42.89  77.00  60.00  101
 13  \w     13.00 114.00   1.00    3.00    --   42.89  77.00 -30.00  101
 14  \w     13.00 114.00   1.00    3.00    --   42.89  77.00 120.00  101
 15  \w     42.00 125.00   1.00   36.00    --  111.00-135.00 172.84   83
 16  \w     81.00 178.00   1.00   36.00    --  111.00  76.00-157.60   97
 17  \w     81.00 178.00   1.00   36.00    --  111.00  77.00-174.99   97
 18  \w     83.00 178.00   1.00   36.00    --  111.00  67.00  93.51   95
 19  \w     41.00 118.00   1.00   36.00    --  111.00-125.00-180.00   77
 20  \w     83.00 178.00   1.00   36.00    --  111.00  67.00 119.17   95
 21  \w     41.00 118.00   1.00   36.00    --  111.00-125.00  90.00   77
 22  \w     85.00 178.00   1.00   36.00    --  111.00  61.00 150.00   93
 23  \w     81.00 178.00   1.00   36.00    --  111.00  77.00   0.00   97
 24  \w     85.00 178.00   1.00   36.00    --  111.00  61.00-180.00   93
 25  \w     81.00  99.00   1.00   36.00    --  111.00  77.00-120.00   18
;
_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      0.0048279000
_diffrn_orient_matrix_UB_12      -0.0549757000
_diffrn_orient_matrix_UB_13      -0.0636502000
_diffrn_orient_matrix_UB_21      -0.1211924000
_diffrn_orient_matrix_UB_22      0.0170875000
_diffrn_orient_matrix_UB_23      -0.0198526000
_diffrn_orient_matrix_UB_31      0.0329470000
_diffrn_orient_matrix_UB_32      0.0713527000
_diffrn_orient_matrix_UB_33      -0.0442356000
_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  0.0482
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            52376
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.847
_diffrn_reflns_theta_min         3.491
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.817
_exptl_absorpt_correction_T_max  0.4719
_exptl_absorpt_correction_T_min  0.3659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0758 before and 0.0621 after correction.
The Ratio of minimum to maximum transmission is 0.7754.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       needle
_exptl_crystal_F_000             1752
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.057
_refine_diff_density_max         1.349
_refine_diff_density_min         -2.032
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         8070
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.166
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0436P)^2^+10.7910P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.0993
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7300
_reflns_number_total             8070
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc09428h2.cif
_cod_data_source_block           compound6
_cod_depositor_comments
'Adding full bibliography for 1557041--1557044.cif.'
_cod_original_cell_volume        3973.69(14)
_cod_database_code               1557043
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C46 H52 Au Cl N2'
_diffrn_oxdiff_digest_frames
;
01071d1866e4709d36cd4011d2725c5e4e02433771e
;
_diffrn_oxdiff_digest_hkl
;
01e0c398667e88513b8973cf71c8ce26cf45ec
;
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     43.65
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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 Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20), C29(H29),
 C30(H30), C32(H32), C33(H33), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39),
  C40(H40), C41(H41), C42(H42), C43(H43), C44(H44)
2.c 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), C46(H46A,H46B,H46C)
;
_shelx_res_checksum              46298
_olex2_date_sample_data_collection 2019-07-04
_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 2.156
_oxdiff_exptl_absorpt_empirical_full_min 0.536