#------------------------------------------------------------------------------
#$Date: 2021-09-30 05:22:18 +0300 (Thu, 30 Sep 2021) $
#$Revision: 269400 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/24/2022481.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_2022481
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 Br N O'
_chemical_formula_moiety         'C21 H26 Br N O'
_chemical_formula_sum            'C21 H26 Br N O'
_chemical_formula_weight         388.34
_chemical_name_systematic
;
(E)-6-{[(4-Bromophenyl)imino]methyl}-2,4-di-tert-butylphenol
;
_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
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.1557(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.4450(3)
_cell_length_b                   10.69412(16)
_cell_length_c                   10.15010(17)
_cell_measurement_reflns_used    13594
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.3210
_cell_measurement_theta_min      2.9920
_cell_volume                     1893.58(5)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2012)
;
_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
;
olex2.solve 1.3 (Bourhis et al.,  2015)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3620
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Agilent SuperNova Dual Source diffractometer with an Atlas detector'
_diffrn_measurement_method       'ω and π scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            28200
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.874
_diffrn_reflns_theta_min         3.001
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.178
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69220
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2012)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       needle
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4491
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0261
_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)+(0.0215P)²+1.2915P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0558
_refine_ls_wR_factor_ref         0.0595
_reflns_number_gt                3799
_reflns_number_total             4491
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wv3002sup1.cif
_cod_data_source_block           3_100K
_cod_database_code               2022481
_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   0.561
_shelx_estimated_absorpt_t_max   0.899
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
Br Br1 -0.13933(2) 0.43538(2) -0.28775(2) 0.02035(6) Uani d 1 . .
O O1 0.18475(7) 0.01027(11) 0.15496(11) 0.0181(2) Uani d 1 . .
N N1 0.11754(8) 0.19817(13) 0.03472(13) 0.0166(3) Uani d 1 . .
C C1 0.23415(9) 0.09407(15) 0.20904(15) 0.0146(3) Uani d 1 . .
C C2 0.29006(9) 0.05468(14) 0.30067(15) 0.0138(3) Uani d 1 . .
C C3 0.33886(9) 0.14656(15) 0.35168(15) 0.0144(3) Uani d 1 . .
H H3 0.376570 0.121268 0.413895 0.017 Uiso calc 1 . .
C C4 0.33593(9) 0.27321(15) 0.31735(15) 0.0142(3) Uani d 1 . .
C C5 0.27967(9) 0.30790(15) 0.22833(16) 0.0154(3) Uani d 1 . .
H H5 0.275740 0.393149 0.202869 0.019 Uiso calc 1 . .
C C6 0.22853(9) 0.22134(15) 0.17486(15) 0.0150(3) Uani d 1 . .
C C7 0.16834(9) 0.26823(15) 0.08879(16) 0.0174(3) Uani d 1 . .
H H7 0.166524 0.355509 0.071650 0.021 Uiso calc 1 . .
C C8 0.05948(9) 0.25507(15) -0.04414(15) 0.0158(3) Uani d 1 . .
C C9 0.07046(10) 0.36729(16) -0.11150(17) 0.0208(4) Uani d 1 . .
H H9 0.118968 0.407533 -0.107976 0.025 Uiso calc 1 . .
C C10 0.01145(10) 0.42060(16) -0.18335(16) 0.0205(4) Uani d 1 . .
H H10 0.019048 0.497335 -0.228634 0.025 Uiso calc 1 . .
C C11 -0.05873(9) 0.36073(15) -0.18841(15) 0.0160(3) Uani d 1 . .
C C12 -0.07095(9) 0.24801(15) -0.12469(16) 0.0181(3) Uani d 1 . .
H H12 -0.119309 0.207431 -0.129914 0.022 Uiso calc 1 . .
C C13 -0.01112(9) 0.19534(15) -0.05293(16) 0.0179(3) Uani d 1 . .
H H13 -0.018570 0.117663 -0.009402 0.021 Uiso calc 1 . .
C C14 0.29671(9) -0.08308(14) 0.34338(15) 0.0153(3) Uani d 1 . .
C C15 0.36162(10) -0.10331(16) 0.44310(17) 0.0206(4) Uani d 1 . .
H H15A 0.351478 -0.054064 0.522594 0.031 Uiso calc 1 . .
H H15B 0.410326 -0.076645 0.404282 0.031 Uiso calc 1 . .
H H15C 0.364567 -0.192154 0.466219 0.031 Uiso calc 1 . .
C C16 0.31359(10) -0.16574(15) 0.22250(17) 0.0204(4) Uani d 1 . .
H H16A 0.362649 -0.140865 0.183675 0.031 Uiso calc 1 . .
H H16B 0.272616 -0.155370 0.157158 0.031 Uiso calc 1 . .
H H16C 0.316225 -0.253535 0.249797 0.031 Uiso calc 1 . .
C C17 0.22203(10) -0.12617(16) 0.40988(17) 0.0205(4) Uani d 1 . .
H H17A 0.179111 -0.116069 0.348292 0.031 Uiso calc 1 . .
H H17B 0.212820 -0.075515 0.488723 0.031 Uiso calc 1 . .
H H17C 0.226611 -0.214355 0.434947 0.031 Uiso calc 1 . .
C C18 0.39307(9) 0.36988(14) 0.37038(15) 0.0152(3) Uani d 1 . .
C C19 0.45373(10) 0.39566(18) 0.26508(17) 0.0239(4) Uani d 1 . .
H H19A 0.428702 0.426618 0.184911 0.036 Uiso calc 1 . .
H H19B 0.481412 0.318215 0.245215 0.036 Uiso calc 1 . .
H H19C 0.489891 0.458656 0.297712 0.036 Uiso calc 1 . .
C C20 0.43335(11) 0.32435(17) 0.49562(17) 0.0252(4) Uani d 1 . .
H H20A 0.467029 0.390454 0.529255 0.038 Uiso calc 1 . .
H H20B 0.463885 0.249890 0.475419 0.038 Uiso calc 1 . .
H H20C 0.394933 0.303543 0.562384 0.038 Uiso calc 1 . .
C C21 0.35161(10) 0.49285(16) 0.40367(19) 0.0253(4) Uani d 1 . .
H H21A 0.311491 0.476559 0.468845 0.038 Uiso calc 1 . .
H H21B 0.328419 0.527413 0.323523 0.038 Uiso calc 1 . .
H H21C 0.388530 0.552878 0.439846 0.038 Uiso calc 1 . .
H H1 0.1539(11) 0.051(2) 0.106(2) 0.048(7) 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'
Br Br -0.2901 2.4595 '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
C1 O1 H1 . . 107.4(16) ?
C7 N1 C8 . . 118.68(14) ?
O1 C1 C2 . . 120.42(14) ?
O1 C1 C6 . . 119.65(14) ?
C6 C1 C2 . . 119.92(14) ?
C1 C2 C14 . . 121.53(13) ?
C3 C2 C1 . . 116.97(14) ?
C3 C2 C14 . . 121.51(14) ?
C2 C3 H3 . . 117.8 ?
C2 C3 C4 . . 124.48(15) ?
C4 C3 H3 . . 117.8 ?
C3 C4 C18 . . 122.83(14) ?
C5 C4 C3 . . 116.59(14) ?
C5 C4 C18 . . 120.55(14) ?
C4 C5 H5 . . 119.1 ?
C4 C5 C6 . . 121.90(15) ?
C6 C5 H5 . . 119.1 ?
C1 C6 C7 . . 122.09(14) ?
C5 C6 C1 . . 120.12(14) ?
C5 C6 C7 . . 117.73(14) ?
N1 C7 C6 . . 123.57(15) ?
N1 C7 H7 . . 118.2 ?
C6 C7 H7 . . 118.2 ?
C9 C8 N1 . . 122.97(14) ?
C13 C8 N1 . . 117.90(14) ?
C13 C8 C9 . . 119.13(15) ?
C8 C9 H9 . . 119.7 ?
C10 C9 C8 . . 120.68(15) ?
C10 C9 H9 . . 119.7 ?
C9 C10 H10 . . 120.4 ?
C11 C10 C9 . . 119.11(16) ?
C11 C10 H10 . . 120.4 ?
C10 C11 Br1 . . 118.57(12) ?
C10 C11 C12 . . 121.55(15) ?
C12 C11 Br1 . . 119.87(12) ?
C11 C12 H12 . . 120.6 ?
C11 C12 C13 . . 118.75(15) ?
C13 C12 H12 . . 120.6 ?
C8 C13 C12 . . 120.75(15) ?
C8 C13 H13 . . 119.6 ?
C12 C13 H13 . . 119.6 ?
C2 C14 C16 . . 109.81(13) ?
C15 C14 C2 . . 112.09(13) ?
C15 C14 C16 . . 107.61(13) ?
C15 C14 C17 . . 107.03(13) ?
C17 C14 C2 . . 110.28(13) ?
C17 C14 C16 . . 109.94(13) ?
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 C21 . . 110.36(13) ?
C19 C18 C4 . . 109.05(13) ?
C19 C18 C21 . . 109.00(14) ?
C20 C18 C4 . . 111.95(13) ?
C20 C18 C19 . . 108.70(14) ?
C20 C18 C21 . . 107.73(14) ?
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
Br1 C11 . 1.9034(15) ?
O1 C1 . 1.3581(19) ?
O1 H1 . 0.854(10) ?
N1 C7 . 1.283(2) ?
N1 C8 . 1.426(2) ?
C1 C2 . 1.410(2) ?
C1 C6 . 1.408(2) ?
C2 C3 . 1.399(2) ?
C2 C14 . 1.540(2) ?
C3 H3 . 0.9500 ?
C3 C4 . 1.399(2) ?
C4 C5 . 1.383(2) ?
C4 C18 . 1.533(2) ?
C5 H5 . 0.9500 ?
C5 C6 . 1.394(2) ?
C6 C7 . 1.453(2) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.395(2) ?
C8 C13 . 1.390(2) ?
C9 H9 . 0.9500 ?
C9 C10 . 1.383(2) ?
C10 H10 . 0.9500 ?
C10 C11 . 1.383(2) ?
C11 C12 . 1.385(2) ?
C12 H12 . 0.9500 ?
C12 C13 . 1.390(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.532(2) ?
C14 C16 . 1.541(2) ?
C14 C17 . 1.540(2) ?
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 . 1.531(2) ?
C18 C20 . 1.530(2) ?
C18 C21 . 1.539(2) ?
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 . 0.854(10) 1.842(14) 2.6257(18) 152(2) 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
Br1 C11 C12 C13 . . . . 179.90(12) ?
O1 C1 C2 C3 . . . . 179.87(14) ?
O1 C1 C2 C14 . . . . -0.6(2) ?
O1 C1 C6 C5 . . . . -179.06(14) ?
O1 C1 C6 C7 . . . . 3.7(2) ?
N1 C8 C9 C10 . . . . -177.94(16) ?
N1 C8 C13 C12 . . . . 177.87(15) ?
C1 C2 C3 C4 . . . . -0.4(2) ?
C1 C2 C14 C15 . . . . 179.83(14) ?
C1 C2 C14 C16 . . . . 60.27(19) ?
C1 C2 C14 C17 . . . . -61.03(19) ?
C1 C6 C7 N1 . . . . -2.1(3) ?
C2 C1 C6 C5 . . . . 2.0(2) ?
C2 C1 C6 C7 . . . . -175.24(15) ?
C2 C3 C4 C5 . . . . 1.1(2) ?
C2 C3 C4 C18 . . . . -176.87(15) ?
C3 C2 C14 C15 . . . . -0.6(2) ?
C3 C2 C14 C16 . . . . -120.18(16) ?
C3 C2 C14 C17 . . . . 118.52(16) ?
C3 C4 C5 C6 . . . . -0.2(2) ?
C3 C4 C18 C19 . . . . 100.62(18) ?
C3 C4 C18 C20 . . . . -19.7(2) ?
C3 C4 C18 C21 . . . . -139.68(16) ?
C4 C5 C6 C1 . . . . -1.3(2) ?
C4 C5 C6 C7 . . . . 176.08(15) ?
C5 C4 C18 C19 . . . . -77.25(19) ?
C5 C4 C18 C20 . . . . 162.43(15) ?
C5 C4 C18 C21 . . . . 42.4(2) ?
C5 C6 C7 N1 . . . . -179.34(16) ?
C6 C1 C2 C3 . . . . -1.2(2) ?
C6 C1 C2 C14 . . . . 178.39(14) ?
C7 N1 C8 C9 . . . . 28.0(2) ?
C7 N1 C8 C13 . . . . -151.64(16) ?
C8 N1 C7 C6 . . . . 177.74(14) ?
C8 C9 C10 C11 . . . . -0.4(3) ?
C9 C8 C13 C12 . . . . -1.8(2) ?
C9 C10 C11 Br1 . . . . 180.00(13) ?
C9 C10 C11 C12 . . . . -0.9(3) ?
C10 C11 C12 C13 . . . . 0.8(2) ?
C11 C12 C13 C8 . . . . 0.6(2) ?
C13 C8 C9 C10 . . . . 1.7(3) ?
C14 C2 C3 C4 . . . . -179.94(15) ?
C18 C4 C5 C6 . . . . 177.76(14) ?

_cod_database_fobs_code 2022481
