Crystal structure of 2-((1H-benzo[d]imidazol-2-ylimino)methyl)-4,6-di-tert-butylphenol, C22H27N3O
Xing, Ai-Ping; Zeng, Dai; Zhang, Shu-Ling; Wei, Jun-Jun; Guo, Da-Feng; Zeitschrift für Kristallographie - New Crystal Structures 234 (2019) 851–853; doi:10.1515/ncrs-2019-0009

data_8105871
_publ_section_title
;
 Crystal structure of
 2-((1H-benzo[d]imidazol-2-ylimino)methyl)-4,6-di-tert-butylphenol,
 C22H27N3O
;
_journal_issue                   5
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              851
_journal_page_last               853
_journal_paper_doi               10.1515/ncrs-2019-0009
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C22 H27 N3 O'
_chemical_formula_sum            'C22 H27 N3 O'
_chemical_formula_weight         349.46
_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   mixed
_atom_sites_solution_primary     iterative
_cell_angle_alpha                90
_cell_angle_beta                 90.9652(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.4984(4)
_cell_length_b                   11.4221(3)
_cell_length_c                   9.79600(19)
_cell_measurement_reflns_used    6373
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6660
_cell_measurement_theta_min      4.5320
_cell_volume                     2069.51(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -29.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000   90.0000 98

  2 omega -102.00  -15.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  -30.0000 87

  3 omega  -32.00   55.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461  -57.0000 -120.0000 87

  4 omega  -33.00   65.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461  -77.0000 -120.0000 98

  5 omega  -33.00   65.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461  -77.0000   90.0000 98

  6 omega   57.00  111.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461  178.0000  150.0000 54

  7 omega  -32.00   55.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461  -57.0000   30.0000 87

  8 omega   14.00  107.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461   37.0000 -180.0000 93

  9 omega   11.00   86.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461 -116.0000 -172.0000 75

 10 omega   38.00  109.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 71

 11 omega   37.00   91.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 54

 12 omega   38.00   99.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 61

 13 omega   38.00  109.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 71

 14 omega  100.00  178.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 78

 15 omega   37.00   91.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 54

 16 omega   37.00   91.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 54

 17 omega   88.00  178.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 90

 18 omega   88.00  178.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 90

 19 omega   57.00  150.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  150.0000 93

 20 omega   79.00  177.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 98

 21 omega  -50.00   11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  116.0000  -83.0000 61

 22 omega -103.00   -5.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000 -120.0000 98

 23 omega    8.00  106.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461   77.0000   60.0000 98

 24 omega    8.00  106.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461   77.0000  -60.0000 98

 25 omega    8.00  106.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461   77.0000 -180.0000 98

 26 omega    8.00  106.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461   77.0000    0.0000 98

 27 omega  -32.00   55.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461  -57.0000  150.0000 87

 28 omega    8.00  106.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461   77.0000  120.0000 98

 29 omega    8.00  106.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461   77.0000 -120.0000 98

 30 omega   -4.00   77.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461  -99.0000  -30.0000 81

 31 omega   18.00  105.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461   57.0000 -180.0000 87

 32 omega   57.00  111.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461  178.0000   90.0000 54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0503281000
_diffrn_orient_matrix_UB_12      0.1027544000
_diffrn_orient_matrix_UB_13      0.0383381000
_diffrn_orient_matrix_UB_21      0.0649439000
_diffrn_orient_matrix_UB_22      -0.0843954000
_diffrn_orient_matrix_UB_23      0.0047492000
_diffrn_orient_matrix_UB_31      0.0132982000
_diffrn_orient_matrix_UB_32      0.0231348000
_diffrn_orient_matrix_UB_33      -0.1524761000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18885
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.039
_diffrn_reflns_theta_max         67.039
_diffrn_reflns_theta_min         4.550
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.545
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3686
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0605
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1048P)^2^+0.2761P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1637
_refine_ls_wR_factor_ref         0.1773
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2825
_reflns_number_total             3686
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2019-0009_suppl.cif
_cod_data_source_block           2018l4
_cod_database_code               8105871
_chemical_oxdiff_formula         C15H15O3N
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.899
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Restrained distances
 C19-C22
 1.55 with sigma of 0.02
 C19-C21A
 1.55 with sigma of 0.02
 C22A-C19
 1.55 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C21) = Uanis(C21A)
Uanis(C22) = Uanis(C22A)
Uanis(C20) = Uanis(C20A)
4. Others
 Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=Sof(C21A)=Sof(H21D)=Sof(H21E)=
 Sof(H21F)=Sof(C22A)=Sof(H22D)=Sof(H22E)=Sof(H22F)=1-FVAR(1)
 Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=
 Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=FVAR(1)
5.a Riding coordinates:
 C21A(H21D,H21E,H21F)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14)
5.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C20(H20A,H20B,
 H20C), C20A(H20D,H20E,H20F), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C),
 C22A(H22D,H22E,H22F)
;
_olex2_submission_special_instructions 'No special instructions were received'