#------------------------------------------------------------------------------
#$Date: 2021-09-30 05:22:18 +0300 (Thu, 30 Sep 2021) $
#$Revision: 269400 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/24/2022474.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_2022474
loop_
_publ_author_name
'Mason, Helen E.'
'Howard, Judith A. K.'
'Sparkes, Hazel A.'
_publ_section_title
;
 Selected solid-state behaviour of three di-tert-butyl-substituted
 N-salicylideneaniline derivatives: temperature-induced phase
 transitions and chromic behaviour
;
_journal_coeditor_code           WV3002
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              659
_journal_page_last               667
_journal_paper_doi               10.1107/S2053229621008780
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C21 H26 Cl N O'
_chemical_formula_moiety         'C21 H26 Cl N O'
_chemical_formula_sum            'C21 H26 Cl N O'
_chemical_formula_weight         343.88
_chemical_name_systematic
;
(E)-2,4-Di-tert-butyl-6-{[(4-chlorophenyl)imino]methyl}phenol
;
_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     direct
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.123(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.3623(8)
_cell_length_b                   10.6691(4)
_cell_length_c                   10.1512(6)
_cell_measurement_reflns_used    3057
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.3810
_cell_measurement_theta_min      2.7840
_cell_volume                     1880.41(16)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1511
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Oxford Diffraction Xcalibur Sapphire3 Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14119
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.770
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2018)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.351
_exptl_crystal_size_mid          0.312
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.715
_refine_diff_density_min         -0.395
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0716
_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/[σ²(Fo²)+(0.0974P)²+0.0284P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1664
_refine_ls_wR_factor_ref         0.1841
_reflns_number_gt                2869
_reflns_number_total             3860
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wv3002sup1.cif
_cod_data_source_block           2_120K
_cod_original_cell_volume        1880.41(15)
_cod_database_code               2022474
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.930
_shelx_estimated_absorpt_t_max   0.980
loop_
_space_group_symop_operation_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 1.13720(4) 0.42872(7) 0.21972(7) 0.0291(2) Uani d 1 . .
O O1 0.81756(11) 0.01140(18) 0.6549(2) 0.0234(5) Uani d 1 . .
N N1 0.88643(13) 0.2000(2) 0.5364(2) 0.0221(5) Uani d 1 . .
C C1 0.76870(15) 0.0957(2) 0.7100(3) 0.0190(6) Uani d 1 . .
C C2 0.71226(15) 0.0563(2) 0.8000(2) 0.0176(6) Uani d 1 . .
C C3 0.66347(15) 0.1482(2) 0.8507(2) 0.0181(6) Uani d 1 . .
H H3 0.625047 0.122581 0.911448 0.022 Uiso calc 1 . .
C C4 0.66710(15) 0.2756(2) 0.8182(2) 0.0185(6) Uani d 1 . .
C C5 0.72423(16) 0.3103(2) 0.7315(3) 0.0207(6) Uani d 1 . .
H H5 0.728888 0.396075 0.707699 0.025 Uiso calc 1 . .
C C6 0.77554(15) 0.2236(2) 0.6774(3) 0.0206(6) Uani d 1 . .
C C7 0.83633(16) 0.2707(3) 0.5927(3) 0.0222(6) Uani d 1 . .
H H7 0.839241 0.358479 0.578040 0.027 Uiso calc 1 . .
C C8 0.94437(16) 0.2567(3) 0.4578(3) 0.0220(6) Uani d 1 . .
C C9 0.93356(16) 0.3698(3) 0.3908(3) 0.0259(7) Uani d 1 . .
H H9 0.885128 0.410993 0.395257 0.031 Uiso calc 1 . .
C C10 0.99246(17) 0.4225(3) 0.3180(3) 0.0263(7) Uani d 1 . .
H H10 0.984787 0.499450 0.272853 0.032 Uiso calc 1 . .
C C11 1.06281(16) 0.3616(3) 0.3118(3) 0.0228(6) Uani d 1 . .
C C12 1.07459(15) 0.2483(3) 0.3757(3) 0.0237(6) Uani d 1 . .
H H12 1.122888 0.206920 0.369549 0.028 Uiso calc 1 . .
C C13 1.01569(16) 0.1963(3) 0.4480(3) 0.0232(6) Uani d 1 . .
H H13 1.023543 0.118641 0.491774 0.028 Uiso calc 1 . .
C C14 0.70465(16) -0.0826(2) 0.8414(3) 0.0202(6) Uani d 1 . .
C C15 0.68718(17) -0.1644(2) 0.7200(3) 0.0250(6) Uani d 1 . .
H H15A 0.638221 -0.138041 0.680534 0.037 Uiso calc 1 . .
H H15B 0.683619 -0.252443 0.746784 0.037 Uiso calc 1 . .
H H15C 0.728589 -0.154781 0.655291 0.037 Uiso calc 1 . .
C C16 0.77948(17) -0.1277(3) 0.9081(3) 0.0248(6) Uani d 1 . .
H H16A 0.822818 -0.116117 0.847594 0.037 Uiso calc 1 . .
H H16B 0.774709 -0.216640 0.930608 0.037 Uiso calc 1 . .
H H16C 0.788512 -0.078912 0.988470 0.037 Uiso calc 1 . .
C C17 0.63909(17) -0.1029(3) 0.9408(3) 0.0256(6) Uani d 1 . .
H H17A 0.649505 -0.054348 1.020799 0.038 Uiso calc 1 . .
H H17B 0.635716 -0.192137 0.963089 0.038 Uiso calc 1 . .
H H17C 0.590270 -0.075304 0.901822 0.038 Uiso calc 1 . .
C C18 0.60941(15) 0.3719(2) 0.8713(3) 0.0190(6) Uani d 1 . .
C C19 0.65006(19) 0.4970(3) 0.9009(3) 0.0372(8) Uani d 1 . .
H H19A 0.692735 0.482484 0.962350 0.056 Uiso calc 1 . .
H H19B 0.613254 0.555566 0.940291 0.056 Uiso calc 1 . .
H H19C 0.670102 0.532543 0.818786 0.056 Uiso calc 1 . .
C C20 0.54766(18) 0.3952(3) 0.7656(3) 0.0349(8) Uani d 1 . .
H H20A 0.572239 0.425402 0.684790 0.052 Uiso calc 1 . .
H H20B 0.511059 0.458194 0.797330 0.052 Uiso calc 1 . .
H H20C 0.520259 0.316787 0.747190 0.052 Uiso calc 1 . .
C C21 0.57028(19) 0.3278(3) 0.9979(3) 0.0338(8) Uani d 1 . .
H H21A 0.538460 0.254103 0.978936 0.051 Uiso calc 1 . .
H H21B 0.537700 0.395173 1.032490 0.051 Uiso calc 1 . .
H H21C 0.609591 0.305934 1.063367 0.051 Uiso calc 1 . .
H H1 0.848(2) 0.056(3) 0.607(4) 0.055(12) 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'
Cl Cl 0.1484 0.1585 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
24 3 0 0.0476
5 0 -14 0.1436
-5 0 14 0.1436
-1 -3 0 0.1367
-24 -3 0 0.0476
1 3 0 0.1367
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
C1 O1 H1 . . 104(2) ?
C7 N1 C8 . . 118.7(2) ?
O1 C1 C2 . . 120.5(2) ?
O1 C1 C6 . . 119.5(2) ?
C2 C1 C6 . . 120.1(2) ?
C1 C2 C14 . . 121.6(2) ?
C3 C2 C1 . . 117.0(2) ?
C3 C2 C14 . . 121.4(2) ?
C2 C3 H3 . . 117.7 ?
C2 C3 C4 . . 124.7(2) ?
C4 C3 H3 . . 117.7 ?
C3 C4 C18 . . 122.6(2) ?
C5 C4 C3 . . 116.3(2) ?
C5 C4 C18 . . 121.1(2) ?
C4 C5 H5 . . 118.9 ?
C4 C5 C6 . . 122.2(2) ?
C6 C5 H5 . . 118.9 ?
C1 C6 C7 . . 122.4(2) ?
C5 C6 C1 . . 119.7(2) ?
C5 C6 C7 . . 117.9(2) ?
N1 C7 C6 . . 123.6(3) ?
N1 C7 H7 . . 118.2 ?
C6 C7 H7 . . 118.2 ?
C9 C8 N1 . . 123.2(2) ?
C9 C8 C13 . . 118.7(2) ?
C13 C8 N1 . . 118.1(2) ?
C8 C9 H9 . . 119.6 ?
C10 C9 C8 . . 120.8(3) ?
C10 C9 H9 . . 119.6 ?
C9 C10 H10 . . 120.4 ?
C9 C10 C11 . . 119.2(3) ?
C11 C10 H10 . . 120.4 ?
C10 C11 Cl1 . . 119.0(2) ?
C10 C11 C12 . . 121.1(2) ?
C12 C11 Cl1 . . 119.9(2) ?
C11 C12 H12 . . 120.3 ?
C13 C12 C11 . . 119.4(3) ?
C13 C12 H12 . . 120.3 ?
C8 C13 H13 . . 119.7 ?
C12 C13 C8 . . 120.7(3) ?
C12 C13 H13 . . 119.7 ?
C15 C14 C2 . . 110.0(2) ?
C15 C14 C16 . . 109.8(2) ?
C16 C14 C2 . . 110.3(2) ?
C17 C14 C2 . . 112.2(2) ?
C17 C14 C15 . . 107.5(2) ?
C17 C14 C16 . . 107.0(2) ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15B . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C14 C16 H16A . . 109.5 ?
C14 C16 H16B . . 109.5 ?
C14 C16 H16C . . 109.5 ?
H16A C16 H16B . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C14 C17 H17A . . 109.5 ?
C14 C17 H17B . . 109.5 ?
C14 C17 H17C . . 109.5 ?
H17A C17 H17B . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C4 C18 C19 . . 110.5(2) ?
C4 C18 C20 . . 108.6(2) ?
C20 C18 C19 . . 108.4(2) ?
C21 C18 C4 . . 112.4(2) ?
C21 C18 C19 . . 107.9(2) ?
C21 C18 C20 . . 109.0(2) ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19B . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C18 C20 H20A . . 109.5 ?
C18 C20 H20B . . 109.5 ?
C18 C20 H20C . . 109.5 ?
H20A C20 H20B . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C18 C21 H21A . . 109.5 ?
C18 C21 H21B . . 109.5 ?
C18 C21 H21C . . 109.5 ?
H21A C21 H21B . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 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
Cl1 C11 . 1.750(3) ?
O1 C1 . 1.357(3) ?
O1 H1 . 0.86(4) ?
N1 C7 . 1.286(3) ?
N1 C8 . 1.421(3) ?
C1 C2 . 1.406(4) ?
C1 C6 . 1.409(4) ?
C2 C3 . 1.395(4) ?
C2 C14 . 1.545(4) ?
C3 H3 . 0.9500 ?
C3 C4 . 1.400(4) ?
C4 C5 . 1.378(4) ?
C4 C18 . 1.534(3) ?
C5 H5 . 0.9500 ?
C5 C6 . 1.398(4) ?
C6 C7 . 1.453(4) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.397(4) ?
C8 C13 . 1.400(4) ?
C9 H9 . 0.9500 ?
C9 C10 . 1.382(4) ?
C10 H10 . 0.9500 ?
C10 C11 . 1.385(4) ?
C11 C12 . 1.386(4) ?
C12 H12 . 0.9500 ?
C12 C13 . 1.377(4) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.540(4) ?
C14 C16 . 1.541(4) ?
C14 C17 . 1.538(4) ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
C18 C19 . 1.539(4) ?
C18 C20 . 1.535(4) ?
C18 C21 . 1.529(4) ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 0.9800 ?
C20 H20A . 0.9800 ?
C20 H20B . 0.9800 ?
C20 H20C . 0.9800 ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
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
_geom_hbond_publ_flag
O1 H1 N1 . 0.86(4) 1.82(4) 2.633(3) 157(4) yes
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Cl1 C11 C12 C13 . . . . 179.9(2) ?
O1 C1 C2 C3 . . . . -179.0(2) ?
O1 C1 C2 C14 . . . . 1.1(4) ?
O1 C1 C6 C5 . . . . 178.5(2) ?
O1 C1 C6 C7 . . . . -3.9(4) ?
N1 C8 C9 C10 . . . . 178.5(3) ?
N1 C8 C13 C12 . . . . -178.6(2) ?
C1 C2 C3 C4 . . . . -0.1(4) ?
C1 C2 C14 C15 . . . . -60.5(3) ?
C1 C2 C14 C16 . . . . 60.8(3) ?
C1 C2 C14 C17 . . . . 179.9(2) ?
C1 C6 C7 N1 . . . . 3.0(4) ?
C2 C1 C6 C5 . . . . -2.3(4) ?
C2 C1 C6 C7 . . . . 175.3(3) ?
C2 C3 C4 C5 . . . . -1.0(4) ?
C2 C3 C4 C18 . . . . 176.8(2) ?
C3 C2 C14 C15 . . . . 119.6(3) ?
C3 C2 C14 C16 . . . . -119.1(3) ?
C3 C2 C14 C17 . . . . 0.0(3) ?
C3 C4 C5 C6 . . . . 0.6(4) ?
C3 C4 C18 C19 . . . . 142.8(3) ?
C3 C4 C18 C20 . . . . -98.5(3) ?
C3 C4 C18 C21 . . . . 22.2(4) ?
C4 C5 C6 C1 . . . . 1.0(4) ?
C4 C5 C6 C7 . . . . -176.7(3) ?
C5 C4 C18 C19 . . . . -39.5(3) ?
C5 C4 C18 C20 . . . . 79.2(3) ?
C5 C4 C18 C21 . . . . -160.1(3) ?
C5 C6 C7 N1 . . . . -179.3(3) ?
C6 C1 C2 C3 . . . . 1.8(4) ?
C6 C1 C2 C14 . . . . -178.1(2) ?
C7 N1 C8 C9 . . . . -29.0(4) ?
C7 N1 C8 C13 . . . . 150.7(3) ?
C8 N1 C7 C6 . . . . -178.6(2) ?
C8 C9 C10 C11 . . . . 0.1(4) ?
C9 C8 C13 C12 . . . . 1.1(4) ?
C9 C10 C11 Cl1 . . . . -180.0(2) ?
C9 C10 C11 C12 . . . . 0.9(4) ?
C10 C11 C12 C13 . . . . -0.9(4) ?
C11 C12 C13 C8 . . . . -0.1(4) ?
C13 C8 C9 C10 . . . . -1.2(4) ?
C14 C2 C3 C4 . . . . 179.7(2) ?
C18 C4 C5 C6 . . . . -177.3(2) ?

_cod_database_fobs_code 2022474
