#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/20/2212045.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2212045
loop_
_publ_author_name
'Oleg Ya. Borbulevych'
_publ_section_title
2,6-Di-tert-butyl-4-[(1-methyl-1H-benzimidazol-2-yl)imino]cyclohexa-2,5-dien-1-one
_journal_coeditor_code           BI2151
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o976
_journal_page_last               o977
_journal_paper_doi               10.1107/S1600536807003315
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C22 H27 N3 O'
_chemical_formula_moiety         'C22 H27 N3 O'
_chemical_formula_sum            'C22 H27 N3 O'
_chemical_formula_weight         349.47
_chemical_name_systematic
;
2,6-Di-tert-butyl-4-[(1-methyl-1H-benzimidazol-2-yl)imino]cyclohexa-
2,5-dien-1-one
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.372(4)
_cell_length_b                   6.7816(14)
_cell_length_c                   16.833(3)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      11
_cell_measurement_theta_min      10
_cell_volume                     2097.2(7)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'CAD-4 Software'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0517
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1985
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.64
_diffrn_standards_decay_%        3.7
_diffrn_standards_interval_count 98
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.232
_refine_ls_extinction_coef       0.019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1985
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1490
_refine_ls_R_factor_gt           0.0638
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1333P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1715
_refine_ls_wR_factor_ref         0.2144
_reflns_number_gt                996
_reflns_number_total             1985
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi2151.cif
_cod_data_source_block           I
_cod_original_cell_volume        2097.3(7)
_cod_database_code               2212045
_cod_database_fobs_code          2212045
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.2289(2) 0.2500 0.1741(2) 0.185(3) Uani d S 1
N N1 0.00602(17) 0.2500 0.37636(18) 0.0483(9) Uani d S 1
N N2 -0.06078(17) 0.2500 0.49479(19) 0.0514(9) Uani d S 1
N N3 0.06047(19) 0.2500 0.51014(19) 0.0555(10) Uani d S 1
C C1 0.1793(2) 0.2500 0.2218(3) 0.0792(16) Uani d S 1
C C2 0.1031(2) 0.2500 0.1933(2) 0.0559(11) Uani d S 1
C C3 0.0507(2) 0.2500 0.2479(2) 0.0505(10) Uani d S 1
H H3 0.0026 0.2500 0.2307 0.061 Uiso calc SR 1
C C4 0.0641(2) 0.2500 0.3318(2) 0.0447(10) Uani d S 1
C C5 0.1394(2) 0.2500 0.3583(2) 0.0520(11) Uani d S 1
H H5 0.1492 0.2500 0.4125 0.062 Uiso calc SR 1
C C6 0.1948(2) 0.2500 0.3070(2) 0.0529(11) Uani d S 1
C C7 0.0059(2) 0.2500 0.4586(2) 0.0474(10) Uani d S 1
C C8 -0.0491(2) 0.2500 0.5748(2) 0.0549(11) Uani d S 1
C C9 -0.0953(3) 0.2500 0.6401(3) 0.0700(14) Uani d S 1
H H9 -0.1456 0.2500 0.6340 0.084 Uiso calc SR 1
C C10 -0.0639(4) 0.2500 0.7137(3) 0.0808(16) Uani d S 1
H H10 -0.0933 0.2500 0.7586 0.097 Uiso calc SR 1
C C11 0.0122(4) 0.2500 0.7228(3) 0.0820(16) Uani d S 1
H H11 0.0317 0.2500 0.7738 0.098 Uiso calc SR 1
C C12 0.0581(3) 0.2500 0.6597(3) 0.0745(14) Uani d S 1
H H12 0.1083 0.2500 0.6668 0.089 Uiso calc SR 1
C C13 0.0276(2) 0.2500 0.5831(2) 0.0552(11) Uani d S 1
C C14 0.0887(3) 0.2500 0.1037(3) 0.0743(15) Uani d SU 1
C C15 0.0081(3) 0.2500 0.0870(3) 0.107(2) Uani d SU 1
H H15A -0.0005 0.2500 0.0308 0.160 Uiso d SR 1
H H15B -0.0133 0.1344 0.1102 0.160 Uiso d R 1
C C16 0.1209(3) 0.0659(9) 0.0663(2) 0.149(2) Uani d U 1
H H16A 0.1003 -0.0489 0.0909 0.223 Uiso calc R 1
H H16B 0.1727 0.0656 0.0737 0.223 Uiso calc R 1
H H16C 0.1101 0.0645 0.0105 0.223 Uiso calc R 1
C C17 0.2743(2) 0.2500 0.3350(3) 0.0696(14) Uani d S 1
C C18 0.2788(3) 0.2500 0.4249(3) 0.109(2) Uani d S 1
H H18A 0.3289 0.2500 0.4412 0.164 Uiso d SR 1
H H18B 0.2551 0.3656 0.4453 0.164 Uiso d R 1
C C19 0.3131(2) 0.0645(7) 0.3042(3) 0.1257(19) Uani d . 1
H H19A 0.3139 0.0663 0.2472 0.189 Uiso calc R 1
H H19B 0.2877 -0.0507 0.3223 0.189 Uiso calc R 1
H H19C 0.3621 0.0621 0.3240 0.189 Uiso calc R 1
C C20 -0.1312(2) 0.2500 0.4558(3) 0.0724(14) Uani d S 1
H H20A -0.1690 0.2500 0.4952 0.109 Uiso d SR 1
H H20B -0.1357 0.3656 0.4232 0.109 Uiso d R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C4 N1 C7 . . 125.2(3)
C8 N2 C7 . . 107.4(3)
C8 N2 C20 . . 125.9(3)
C7 N2 C20 . . 126.7(3)
C7 N3 C13 . . 104.7(3)
O1 C1 C6 . . 120.1(4)
O1 C1 C2 . . 119.7(4)
C6 C1 C2 . . 120.2(4)
C3 C2 C1 . . 117.4(4)
C3 C2 C14 . . 123.8(4)
C1 C2 C14 . . 118.9(4)
C2 C3 C4 . . 123.8(4)
C2 C3 H3 . . 118.1
C4 C3 H3 . . 118.1
N1 C4 C3 . . 115.2(3)
N1 C4 C5 . . 127.0(4)
C3 C4 C5 . . 117.8(3)
C6 C5 C4 . . 121.8(4)
C6 C5 H5 . . 119.1
C4 C5 H5 . . 119.1
C5 C6 C1 . . 119.0(4)
C5 C6 C17 . . 121.8(4)
C1 C6 C17 . . 119.1(4)
N3 C7 N2 . . 112.7(3)
N3 C7 N1 . . 130.8(4)
N2 C7 N1 . . 116.6(3)
N2 C8 C9 . . 133.2(5)
N2 C8 C13 . . 104.7(3)
C9 C8 C13 . . 122.0(4)
C10 C9 C8 . . 117.3(5)
C10 C9 H9 . . 121.4
C8 C9 H9 . . 121.4
C9 C10 C11 . . 121.3(5)
C9 C10 H10 . . 119.4
C11 C10 H10 . . 119.4
C12 C11 C10 . . 122.1(5)
C12 C11 H11 . . 118.9
C10 C11 H11 . . 118.9
C11 C12 C13 . . 118.1(5)
C11 C12 H12 . . 121.0
C13 C12 H12 . . 121.0
N3 C13 C12 . . 130.4(4)
N3 C13 C8 . . 110.5(4)
C12 C13 C8 . . 119.2(4)
C15 C14 C16 . . 107.8(3)
C15 C14 C16 . 7_565 107.8(3)
C16 C14 C16 . 7_565 110.6(5)
C15 C14 C2 . . 110.7(4)
C16 C14 C2 . . 110.0(3)
C16 C14 C2 7_565 . 110.0(3)
C14 C15 H15A . . 110.2
C14 C15 H15B . . 109.1
H15A C15 H15B . . 109.5
C14 C16 H16A . . 109.5
C14 C16 H16B . . 109.5
H16A C16 H16B . . 109.5
C14 C16 H16C . . 109.5
H16A C16 H16C . . 109.5
H16B C16 H16C . . 109.5
C18 C17 C6 . . 111.0(4)
C18 C17 C19 . 7_565 108.1(3)
C6 C17 C19 . 7_565 109.8(2)
C18 C17 C19 . . 108.1(3)
C6 C17 C19 . . 109.8(3)
C19 C17 C19 7_565 . 109.9(5)
C17 C18 H18A . . 109.7
C17 C18 H18B . . 109.4
H18A C18 H18B . . 109.5
C17 C19 H19A . . 109.5
C17 C19 H19B . . 109.5
H19A C19 H19B . . 109.5
C17 C19 H19C . . 109.5
H19A C19 H19C . . 109.5
H19B C19 H19C . . 109.5
N2 C20 H20A . . 109.4
N2 C20 H20B . . 109.5
H20A C20 H20B . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.214(5)
N1 C4 . 1.305(5)
N1 C7 . 1.384(5)
N2 C8 . 1.364(5)
N2 C7 . 1.368(5)
N2 C20 . 1.452(5)
N3 C7 . 1.326(5)
N3 C13 . 1.369(5)
C1 C6 . 1.462(6)
C1 C2 . 1.480(6)
C2 C3 . 1.332(5)
C2 C14 . 1.531(6)
C3 C4 . 1.433(6)
C3 H3 . 0.930
C4 C5 . 1.454(5)
C5 C6 . 1.335(5)
C5 H5 . 0.930
C6 C17 . 1.534(6)
C8 C9 . 1.388(6)
C8 C13 . 1.417(6)
C9 C10 . 1.368(7)
C9 H9 . 0.930
C10 C11 . 1.405(8)
C10 H10 . 0.930
C11 C12 . 1.358(7)
C11 H11 . 0.930
C12 C13 . 1.404(6)
C12 H12 . 0.930
C14 C15 . 1.507(7)
C14 C16 . 1.519(5)
C14 C16 7_565 1.519(5)
C15 H15A . 0.960
C15 H15B . 0.960
C16 H16A . 0.960
C16 H16B . 0.960
C16 H16C . 0.960
C17 C18 . 1.517(7)
C17 C19 7_565 1.536(5)
C17 C19 . 1.536(5)
C18 H18A . 0.960
C18 H18B . 0.960
C19 H19A . 0.960
C19 H19B . 0.960
C19 H19C . 0.960
C20 H20A . 0.960
C20 H20B . 0.960
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_4
_geom_torsion
O1 C1 C2 C3 . 180.0
C6 C1 C2 C3 . 0.0
O1 C1 C2 C14 . 0.0
C6 C1 C2 C14 . 180.0
C1 C2 C3 C4 . 0.0
C14 C2 C3 C4 . 180.0
C7 N1 C4 C3 . 180.0
C7 N1 C4 C5 . 0.0
C2 C3 C4 N1 . 180.0
C2 C3 C4 C5 . 0.0
N1 C4 C5 C6 . 180.0
C3 C4 C5 C6 . 0.0
C4 C5 C6 C1 . 0.0
C4 C5 C6 C17 . 180.0
O1 C1 C6 C5 . 180.0
C2 C1 C6 C5 . 0.0
O1 C1 C6 C17 . 0.0
C2 C1 C6 C17 . 180.0
C13 N3 C7 N2 . 0.0
C13 N3 C7 N1 . 180.0
C8 N2 C7 N3 . 0.0
C20 N2 C7 N3 . 180.0
C8 N2 C7 N1 . 180.0
C20 N2 C7 N1 . 0.0
C4 N1 C7 N3 . 0.0
C4 N1 C7 N2 . 180.0
C7 N2 C8 C9 . 180.0000(10)
C20 N2 C8 C9 . 0.0000(10)
C7 N2 C8 C13 . 0.0
C20 N2 C8 C13 . 180.0
N2 C8 C9 C10 . 180.0000(10)
C13 C8 C9 C10 . 0.0000(10)
C8 C9 C10 C11 . 0.0000(10)
C9 C10 C11 C12 . 0.000(2)
C10 C11 C12 C13 . 0.0000(10)
C7 N3 C13 C12 . 180.0
C7 N3 C13 C8 . 0.0
C11 C12 C13 N3 . 180.0
C11 C12 C13 C8 . 0.0000(10)
N2 C8 C13 N3 . 0.0
C9 C8 C13 N3 . 180.0
N2 C8 C13 C12 . 180.0
C9 C8 C13 C12 . 0.0000(10)
C3 C2 C14 C15 . 0.0
C1 C2 C14 C15 . 180.0
C3 C2 C14 C16 . -119.0(3)
C1 C2 C14 C16 . 61.0(3)
C3 C2 C14 C16 7_565 119.0(3)
C1 C2 C14 C16 7_565 -61.0(3)
C5 C6 C17 C18 . 0.0
C1 C6 C17 C18 . 180.0
C5 C6 C17 C19 7_565 -119.5(3)
C1 C6 C17 C19 7_565 60.5(3)
C5 C6 C17 C19 . 119.5(3)
C1 C6 C17 C19 . -60.5(3)
