#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/16/2221678.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_2221678
loop_
_publ_author_name
'Zhao, Yong-Feng'
'Xiong, Jin-Ping'
'Zuo, Yu'
_publ_section_title
3-[(3,5-Di-tert-butyl-2-hydroxybenzylidene)methyleneamino]benzonitrile
_journal_coeditor_code           GW2063
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1141
_journal_paper_doi               10.1107/S1600536809014809
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C22 H26 N2 O'
_chemical_formula_moiety         'C22 H26 N2 O'
_chemical_formula_sum            'C22 H26 N2 O'
_chemical_formula_weight         334.45
_chemical_name_systematic
;
3-[(3,5-Di-tert-butyl-2-hydroxybenzylidene)methyleneamino]benzonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 97.86(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.897(3)
_cell_length_b                   15.684(3)
_cell_length_c                   8.8581(18)
_cell_measurement_reflns_used    7104
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.2
_cell_measurement_theta_min      3.0
_cell_volume                     2050.2(7)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Mercury2'
_diffrn_measurement_method       ω
_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  0.0789
_diffrn_reflns_av_sigmaI/netI    0.0841
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10436
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.084
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3701
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.1682
_refine_ls_R_factor_gt           0.0722
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0819P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1577
_refine_ls_wR_factor_ref         0.1890
_reflns_number_gt                1746
_reflns_number_total             3701
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gw2063.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221678
_cod_database_fobs_code          2221678
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.66011(15) 0.15473(13) 0.7833(2) 0.0653(6) Uani d . 1 . .
C C10 0.72011(19) 0.08905(18) 0.8159(3) 0.0505(8) Uani d . 1 . .
N N2 0.59185(16) 0.11626(15) 1.0309(3) 0.0559(7) Uani d . 1 . .
C C11 0.78194(18) 0.06970(18) 0.7144(3) 0.0492(8) Uani d . 1 . .
C C9 0.71779(18) 0.04083(18) 0.9488(3) 0.0490(7) Uani d . 1 . .
C C14 0.77740(19) -0.02806(19) 0.9807(3) 0.0566(8) Uani d . 1 . .
H H14A 0.7755 -0.0593 1.0695 0.068 Uiso calc R 1 . .
C C12 0.83890(19) 0.00022(19) 0.7535(4) 0.0561(8) Uani d . 1 . .
H H12A 0.8803 -0.0134 0.6876 0.067 Uiso calc R 1 . .
C C1 0.52589(19) 0.1264(2) 1.1329(3) 0.0520(8) Uani d . 1 . .
C C8 0.6525(2) 0.05759(19) 1.0535(3) 0.0534(8) Uani d . 1 . .
H H8A 0.6547 0.0243 1.1407 0.064 Uiso calc R 1 . .
C C13 0.83925(19) -0.05108(18) 0.8837(4) 0.0545(8) Uani d . 1 . .
C C2 0.48863(19) 0.20659(19) 1.1417(3) 0.0563(8) Uani d . 1 . .
H H2B 0.5078 0.2513 1.0850 0.068 Uiso calc R 1 . .
C C3 0.4222(2) 0.2205(2) 1.2357(4) 0.0610(9) Uani d . 1 . .
C C4 0.3933(2) 0.1543(3) 1.3211(4) 0.0703(10) Uani d . 1 . .
H H4A 0.3489 0.1636 1.3834 0.084 Uiso calc R 1 . .
C C6 0.49656(19) 0.0600(2) 1.2181(4) 0.0608(9) Uani d . 1 . .
H H6A 0.5208 0.0057 1.2118 0.073 Uiso calc R 1 . .
C C7 0.3820(2) 0.3038(3) 1.2386(4) 0.0792(11) Uani d . 1 . .
C C5 0.4310(2) 0.0748(2) 1.3128(4) 0.0710(10) Uani d . 1 . .
H H5A 0.4126 0.0304 1.3710 0.085 Uiso calc R 1 . .
C C15 0.9008(2) -0.1292(2) 0.9173(4) 0.0705(10) Uani d . 1 . .
C C17 0.8421(3) -0.2099(2) 0.9016(6) 0.1168(16) Uani d . 1 . .
H H17A 0.8121 -0.2145 0.7989 0.175 Uiso calc R 1 . .
H H17B 0.7977 -0.2068 0.9704 0.175 Uiso calc R 1 . .
H H17C 0.8798 -0.2590 0.9257 0.175 Uiso calc R 1 . .
C C16 0.9728(3) -0.1349(3) 0.8100(7) 0.145(2) Uani d . 1 . .
H H16A 0.9437 -0.1377 0.7065 0.217 Uiso calc R 1 . .
H H16B 1.0088 -0.1851 0.8332 0.217 Uiso calc R 1 . .
H H16C 1.0110 -0.0854 0.8229 0.217 Uiso calc R 1 . .
N N1 0.3495(3) 0.3705(2) 1.2362(5) 0.1135(13) Uani d . 1 . .
C C19 0.7872(2) 0.1226(2) 0.5690(4) 0.0619(9) Uani d . 1 . .
C C20 0.6964(2) 0.1167(2) 0.4636(4) 0.0807(11) Uani d . 1 . .
H H20A 0.6839 0.0581 0.4368 0.121 Uiso calc R 1 . .
H H20B 0.6998 0.1493 0.3728 0.121 Uiso calc R 1 . .
H H20C 0.6488 0.1388 0.5153 0.121 Uiso calc R 1 . .
C C21 0.8071(2) 0.2170(2) 0.6111(4) 0.0871(12) Uani d . 1 . .
H H21A 0.7609 0.2386 0.6665 0.131 Uiso calc R 1 . .
H H21B 0.8079 0.2497 0.5198 0.131 Uiso calc R 1 . .
H H21C 0.8650 0.2212 0.6733 0.131 Uiso calc R 1 . .
C C18 0.9497(3) -0.1256(2) 1.0812(5) 0.1196(17) Uani d . 1 . .
H H18A 0.9058 -0.1221 1.1508 0.179 Uiso calc R 1 . .
H H18B 0.9882 -0.0763 1.0931 0.179 Uiso calc R 1 . .
H H18C 0.9857 -0.1761 1.1021 0.179 Uiso calc R 1 . .
C C22 0.8623(3) 0.0909(3) 0.4806(5) 0.1176(17) Uani d . 1 . .
H H22A 0.8515 0.0322 0.4529 0.176 Uiso calc R 1 . .
H H22B 0.9199 0.0960 0.5434 0.176 Uiso calc R 1 . .
H H22C 0.8625 0.1245 0.3901 0.176 Uiso calc R 1 . .
H H1A 0.618(3) 0.155(3) 0.865(6) 0.166(19) Uiso d . 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
_geom_angle_publ_flag
C10 O1 H1A . . 108(3) ?
O1 C10 C9 . . 119.5(3) ?
O1 C10 C11 . . 119.6(3) ?
C9 C10 C11 . . 120.9(3) ?
C8 N2 C1 . . 120.6(3) ?
C12 C11 C10 . . 116.1(3) ?
C12 C11 C19 . . 121.9(3) ?
C10 C11 C19 . . 122.0(3) ?
C10 C9 C14 . . 119.8(3) ?
C10 C9 C8 . . 122.1(3) ?
C14 C9 C8 . . 118.1(3) ?
C13 C14 C9 . . 122.0(3) ?
C13 C14 H14A . . 119.0 ?
C9 C14 H14A . . 119.0 ?
C11 C12 C13 . . 125.8(3) ?
C11 C12 H12A . . 117.1 ?
C13 C12 H12A . . 117.1 ?
C2 C1 C6 . . 119.5(3) ?
C2 C1 N2 . . 116.9(3) ?
C6 C1 N2 . . 123.6(3) ?
N2 C8 C9 . . 123.1(3) ?
N2 C8 H8A . . 118.4 ?
C9 C8 H8A . . 118.4 ?
C14 C13 C12 . . 115.5(3) ?
C14 C13 C15 . . 121.1(3) ?
C12 C13 C15 . . 123.4(3) ?
C1 C2 C3 . . 119.9(3) ?
C1 C2 H2B . . 120.0 ?
C3 C2 H2B . . 120.0 ?
C4 C3 C2 . . 120.4(3) ?
C4 C3 C7 . . 120.7(3) ?
C2 C3 C7 . . 118.9(3) ?
C5 C4 C3 . . 119.4(3) ?
C5 C4 H4A . . 120.3 ?
C3 C4 H4A . . 120.3 ?
C5 C6 C1 . . 120.1(3) ?
C5 C6 H6A . . 119.9 ?
C1 C6 H6A . . 119.9 ?
N1 C7 C3 . . 178.0(4) ?
C4 C5 C6 . . 120.6(3) ?
C4 C5 H5A . . 119.7 ?
C6 C5 H5A . . 119.7 ?
C17 C15 C16 . . 109.5(3) ?
C17 C15 C18 . . 107.9(3) ?
C16 C15 C18 . . 107.9(3) ?
C17 C15 C13 . . 108.9(3) ?
C16 C15 C13 . . 112.2(3) ?
C18 C15 C13 . . 110.4(3) ?
C15 C17 H17A . . 109.5 ?
C15 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C15 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C22 C19 C20 . . 108.2(3) ?
C22 C19 C21 . . 107.7(3) ?
C20 C19 C21 . . 109.2(3) ?
C22 C19 C11 . . 112.0(3) ?
C20 C19 C11 . . 109.5(2) ?
C21 C19 C11 . . 110.1(3) ?
C19 C20 H20A . . 109.5 ?
C19 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C19 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C19 C21 H21A . . 109.5 ?
C19 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C19 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C15 C18 H18A . . 109.5 ?
C15 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C15 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C19 C22 H22A . . 109.5 ?
C19 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C19 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C10 . 1.369(3) ?
O1 H1A . 1.03(5) ?
C10 C9 . 1.404(4) ?
C10 C11 . 1.405(4) ?
N2 C8 . 1.286(3) ?
N2 C1 . 1.431(3) ?
C11 C12 . 1.395(4) ?
C11 C19 . 1.543(4) ?
C9 C14 . 1.403(4) ?
C9 C8 . 1.456(4) ?
C14 C13 . 1.391(4) ?
C14 H14A . 0.9300 ?
C12 C13 . 1.406(4) ?
C12 H12A . 0.9300 ?
C1 C2 . 1.382(4) ?
C1 C6 . 1.391(4) ?
C8 H8A . 0.9300 ?
C13 C15 . 1.534(4) ?
C2 C3 . 1.396(4) ?
C2 H2B . 0.9300 ?
C3 C4 . 1.387(4) ?
C3 C7 . 1.438(5) ?
C4 C5 . 1.374(4) ?
C4 H4A . 0.9300 ?
C6 C5 . 1.390(4) ?
C6 H6A . 0.9300 ?
C7 N1 . 1.152(4) ?
C5 H5A . 0.9300 ?
C15 C17 . 1.535(4) ?
C15 C16 . 1.530(5) ?
C15 C18 . 1.533(5) ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C19 C22 . 1.534(4) ?
C19 C20 . 1.537(4) ?
C19 C21 . 1.545(4) ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1A N2 . 1.03(5) 1.68(5) 2.612(3) 149(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742223
2 PubChem 139076469
