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_1557041
_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 H45 N2, C H4 O, Br'
_chemical_formula_sum            'C40 H49 Br N2 O'
_chemical_formula_weight         653.72
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_audit_update_record
;
2019-08-14 deposited with the CCDC.	2020-01-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.6410(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.10880(10)
_cell_length_b                   21.1979(2)
_cell_length_c                   15.9518(2)
_cell_measurement_reflns_used    67331
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      31.7600
_cell_measurement_theta_min      1.9140
_cell_volume                     3559.32(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_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 8.0951
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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      6.00  95.00   1.00   11.00    --   25.96  57.00  30.00   89
  2  \w      6.00  95.00   1.00   11.00    --   25.96  57.00-180.00   89
  3  \w      6.00  95.00   1.00   11.00    --   25.96  57.00 120.00   89
  4  \w     12.00  95.00   1.00   11.00    --   25.96-143.00-120.00   83
  5  \w    -43.00  47.00   1.00   11.00    --   25.96 -57.00  30.00   90
  6  \w    -46.00  51.00   1.00   11.00    --   25.96 -38.00 120.00   97
  7  \w     -4.00  96.00   1.00   11.00    --   25.96  77.00-150.00  100
  8  \w    -20.00  68.00   1.00   11.00    --   25.96 -99.00 -30.00   88
  9  \w      0.00  98.00   1.00   11.00    --   25.96  38.00 -60.00   98
 10  \w     -4.00  96.00   1.00   11.00    --   25.96  77.00 -60.00  100
 11  \w    -43.00  47.00   1.00   11.00    --   25.96 -57.00-120.00   90
 12  \w    -49.00  49.00   1.00   11.00    --  -23.50  38.00  30.00   98
 13  \w     35.00 102.00   1.00   11.00    --   25.96 178.00  90.00   67
 14  \w    -47.00  99.00   1.00   11.00    --   25.96   0.00-120.00  146
 15  \w     -4.00  96.00   1.00   11.00    --   25.96  77.00-180.00  100
 16  \w    -47.00  99.00   1.00   11.00    --   25.96   0.00-180.00  146
 17  \w    -47.00  99.00   1.00   11.00    --   25.96   0.00-150.00  146
 18  \w     -4.00  96.00   1.00   11.00    --   25.96  77.00  60.00  100
 19  \w    -47.00  99.00   1.00   11.00    --   25.96   0.00 -90.00  146
 20  \w    -47.00  99.00   1.00   11.00    --   25.96   0.00 -60.00  146
 21  \w    -20.00  68.00   1.00   11.00    --   25.96 -99.00  90.00   88
 22  \w    -47.00  67.00   1.00   11.00    --   25.96   0.00   0.00  114
 23  \w    -47.00  99.00   1.00   11.00    --   25.96   0.00 -30.00  146
;
_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      -0.0611565000
_diffrn_orient_matrix_UB_12      -0.0012701000
_diffrn_orient_matrix_UB_13      -0.0322055000
_diffrn_orient_matrix_UB_21      0.0007125000
_diffrn_orient_matrix_UB_22      -0.0333799000
_diffrn_orient_matrix_UB_23      0.0031564000
_diffrn_orient_matrix_UB_31      -0.0282984000
_diffrn_orient_matrix_UB_32      0.0018971000
_diffrn_orient_matrix_UB_33      0.0339818000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            206381
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.080
_diffrn_reflns_theta_min         1.655
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.187
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.563
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
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    1.220
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.212
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         10453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0302
_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^)+(0.0357P)^2^+2.1231P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0800
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9367
_reflns_number_total             10453
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc09428h2.cif
_cod_data_source_block           compound1
_cod_depositor_comments
'Adding full bibliography for 1557041--1557044.cif.'
_cod_database_code               1557041
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C40 H49 Br N2 O'
_shelx_estimated_absorpt_t_max   0.787
_shelx_estimated_absorpt_t_min   0.642
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_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, All O(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:
 C2(H2), 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)
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), C40(H40A,H40B,H40C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              20867
_olex2_date_sample_data_collection 2018-04-19
_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 1.301
_oxdiff_exptl_absorpt_empirical_full_min 0.900