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_1557042
_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         'C42 H44 N2 Ni O3'
_chemical_formula_sum            'C42 H44 N2 Ni O3'
_chemical_formula_weight         683.50
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-08-01
_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                100.3074(12)
_cell_angle_beta                 95.6535(12)
_cell_angle_gamma                99.0466(12)
_cell_formula_units_Z            2
_cell_length_a                   10.35522(15)
_cell_length_b                   11.18263(16)
_cell_length_c                   16.4194(2)
_cell_measurement_reflns_used    35592
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      76.3250
_cell_measurement_theta_min      4.0500
_cell_volume                     1831.63(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.58a (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      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3114
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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    -64.00  30.00   1.00    2.00    --  -38.50  57.00  30.00   94
  2  \w    -59.00  33.00   1.00    2.00    --  -38.50  38.00   0.00   92
  3  \w    -59.00  33.00   1.00    2.00    --  -38.50  38.00 -90.00   92
  4  \w    -69.00  33.00   1.00    2.00    --  -38.50  77.00 120.00  102
  5  \w     18.00 111.00   1.00    2.00    --   42.89  57.00-180.00   93
  6  \w     22.00 114.00   1.00    2.00    --   42.89  38.00-150.00   92
  7  \w     14.00 112.00   1.00    2.00    --   42.89  70.00-127.81   98
  8  \w     12.00  42.00   1.00    2.00    --   42.89  79.00 119.29   30
  9  \w     22.00 114.00   1.00    2.00    --   42.89  38.00 -60.00   92
 10  \w     12.00  42.00   1.00    2.00    --   42.89  80.00-152.82   30
 11  \w     27.00  97.00   1.00    2.00    --   42.89-125.00-120.00   70
 12  \w     12.00  42.00   1.00    2.00    --   42.89  81.00 -23.90   30
 13  \w     18.00 111.00   1.00    2.00    --   42.89  57.00 120.00   93
 14  \w     14.00 112.00   1.00    2.00    --   42.89  70.00  -1.64   98
 15  \w     22.00 114.00   1.00    2.00    --   42.89  38.00  90.00   92
 16  \w     12.00  42.00   1.00    2.00    --   42.89  79.00 -66.04   30
 17  \w     13.00 113.00   1.00    2.00    --   42.89  74.00  66.98  100
 18  \w     83.00 178.00   1.00    8.00    --  111.00  67.00-114.00   95
 19  \w     84.00 178.00   1.00    8.00    --  111.00  64.00-128.21   94
 20  \w     83.00 178.00   1.00    8.00    --  111.00  69.00 146.68   95
 21  \w     85.00 178.00   1.00    8.00    --  111.00  61.00  84.46   93
 22  \w     85.00 178.00   1.00    8.00    --  111.00  61.00 120.00   93
 23  \w     89.00 178.00   1.00    8.00    --  111.00  45.00 -60.00   89
 24  \w     89.00 178.00   1.00    8.00    --  111.00  45.00-120.00   89
 25  \w     89.00 178.00   1.00    8.00    --  111.00  45.00   0.00   89
 26  \w     40.00 141.00   1.00    8.00    --  111.00 -77.00-150.00  101
 27  \w     84.00 178.00   1.00    8.00    --  111.00  65.00  44.85   94
 28  \w     85.00 178.00   1.00    8.00    --  111.00  61.00  90.00   93
 29  \w     84.00 178.00   1.00    8.00    --  111.00  64.00 165.39   94
 30  \w     83.00 178.00   1.00    8.00    --  111.00  70.00 -30.31   95
 31  \w     40.00 141.00   1.00    8.00    --  111.00 -77.00  60.00  101
 32  \w     85.00 178.00   1.00    8.00    --  111.00  61.00   0.00   93
 33  \w     85.00 178.00   1.00    8.00    --  111.00  61.00 -60.00   93
 34  \w     31.00 107.00   1.00    8.00    --  111.00 -94.00-180.00   76
 35  \w     82.00 178.00   1.00    8.00    --  111.00  71.00  53.86   96
 36  \w     84.00 178.00   1.00    8.00    --  111.00  63.00 129.65   94
 37  \w     85.00 178.00   1.00    8.00    --  111.00  61.00 -30.00   93
 38  \w     89.00 178.00   1.00    8.00    --  111.00  45.00  30.00   89
 39  \w     41.00 113.00   1.00    8.00    --  111.00-125.00 -60.00   72
 40  \w     85.00 178.00   1.00    8.00    --  111.00  61.00-150.00   93
 41  \w     85.00 178.00   1.00    8.00    --  111.00  61.00-180.00   93
 42  \w     85.00 178.00   1.00    8.00    --  111.00  61.00 -90.00   93
 43  \w     85.00 178.00   1.00    8.00    --  111.00  60.00-168.26   93
 44  \w     89.00 178.00   1.00    8.00    --  111.00  45.00  60.00   89
 45  \w     31.00 107.00   1.00    8.00    --  111.00 -94.00  60.00   76
 46  \w     39.00 110.00   1.00    8.00    --  111.00-115.00  35.39   71
 47  \w     31.00 107.00   1.00    8.00    --  111.00 -94.00 150.00   76
 48  \w     85.00 178.00   1.00    8.00    --  111.00  61.00-120.00   93
 49  \w     85.00 178.00   1.00    8.00    --  111.00  61.00  30.00   93
 50  \w     31.00 107.00   1.00    8.00    --  111.00 -94.00 -60.00   76
 51  \w     89.00 178.00   1.00    8.00    --  111.00  45.00 -30.00   89
 52  \w     84.00 110.00   1.00    8.00    --  111.00  63.00 -67.62   26
 53  \w     83.00 174.00   1.00    8.00    --  111.00  67.00  95.68   91
;
_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      0.0903408000
_diffrn_orient_matrix_UB_12      -0.0973466000
_diffrn_orient_matrix_UB_13      -0.0026869000
_diffrn_orient_matrix_UB_21      -0.1111239000
_diffrn_orient_matrix_UB_22      -0.0914854000
_diffrn_orient_matrix_UB_23      0.0232829000
_diffrn_orient_matrix_UB_31      -0.0507573000
_diffrn_orient_matrix_UB_32      -0.0490580000
_diffrn_orient_matrix_UB_33      -0.0932863000
_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  0.0307
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            53689
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.477
_diffrn_reflns_theta_min         2.759
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.073
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.426
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.58a (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 brownish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       plate
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.303
_exptl_crystal_size_min          0.147
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         7620
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0319
_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^)+(0.0417P)^2^+0.9198P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0863
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7232
_reflns_number_total             7620
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc09428h2.cif
_cod_data_source_block           compound5
_cod_depositor_comments
'Adding full bibliography for 1557041--1557044.cif.'
_cod_original_cell_volume        1831.62(5)
_cod_database_code               1557042
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C64 H68 N24 Ni2 O6 '
_diffrn_oxdiff_digest_frames
;
01a4522391558b88d26f1b82f2829c695d0450554bf
;
_diffrn_oxdiff_digest_hkl
;
015e8f4da375ec0cca866e3120b749334e384d
;
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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:
 C22(H22), C25(H25), C34(H34), C37(H37)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C18(H18), C19(H19), C20(H20), C30(H30), C31(H31), C32(H32)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C38(H38A,H38B,H38C), C39(H39A,
 H39B,H39C)
;
_shelx_res_checksum              84999
_olex2_date_sample_data_collection 2019-07-31
_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 2.504
_oxdiff_exptl_absorpt_empirical_full_min 0.544