#------------------------------------------------------------------------------
#$Date: 2018-12-04 05:51:11 +0200 (Tue, 04 Dec 2018) $
#$Revision: 212312 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/27/2242763.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_2242763
loop_
_publ_author_name
'Kansiz, Sevgi'
'Macit, Mustafa'
'Dege, Necmi'
'Pavlenko, Vadim A.'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 (E)-2,4-di-tert-butyl-6-[(3-chloro-4-methylphenylimino)methyl]phenol
;
_journal_coeditor_code           XU5948
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1887
_journal_page_last               1890
_journal_paper_doi               10.1107/S2056989018016377
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C22 H28 Cl N O'
_chemical_formula_moiety         'C22 H28 Cl N O'
_chemical_formula_sum            'C22 H28 Cl N O'
_chemical_formula_weight         357.90
_chemical_name_systematic
(E)-2,4-di-tert-butyl-6-[(3-chloro-4-methylphenylimino)methyl]phenol
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 93.425(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6753(10)
_cell_length_b                   7.0072(6)
_cell_length_c                   15.3749(13)
_cell_measurement_reflns_used    5548
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.71
_cell_measurement_theta_min      2.11
_cell_volume                     1040.51(17)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_reduction
;
X-RED (Stoe & Cie, 2002)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2017/1 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXLXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5895
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.495
_diffrn_reflns_theta_min         2.109
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.9401
_exptl_absorpt_correction_T_min  0.8794
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(X-RED32; Stoe & Cie, 2002)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.740
_exptl_crystal_size_mid          0.650
_exptl_crystal_size_min          0.480
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2300
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0531
_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/[σ²(Fo²)+(0.0964P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1523
_refine_ls_wR_factor_ref         0.1681
_reflns_number_gt                1298
_reflns_number_total             2300
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            xu5948sup1.cif
_cod_data_source_block           I
_cod_database_code               2242763
_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.
;
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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
C C1 0.2129(4) 0.250000 0.2502(2) 0.0799(9) Uani d 1
H H1A 0.122313 0.250000 0.272431 0.120 Uiso d 1
H H1B 0.223846 0.361862 0.215178 0.120 Uiso d 1
C C2 0.3181(3) 0.250000 0.3253(2) 0.0633(8) Uani d 1
C C3 0.2795(3) 0.250000 0.4107(2) 0.0703(9) Uani d 1
H H3 0.185649 0.250000 0.420637 0.084 Uiso calc 1
C C4 0.3723(3) 0.250000 0.4806(2) 0.0700(9) Uani d 1
H H4 0.340566 0.250000 0.536544 0.084 Uiso calc 1
C C5 0.5133(3) 0.250000 0.46997(18) 0.0556(7) Uani d 1
C C6 0.5560(3) 0.250000 0.38600(19) 0.0600(7) Uani d 1
H H6 0.649961 0.250000 0.376348 0.072 Uiso calc 1
C C7 0.4596(3) 0.250000 0.3165(2) 0.0639(8) Uani d 1
C C8 0.5942(3) 0.250000 0.61807(19) 0.0568(7) Uani d 1
H H8 0.502444 0.250000 0.632881 0.068 Uiso calc 1
C C9 0.7006(3) 0.250000 0.68668(18) 0.0521(7) Uani d 1
C C10 0.6637(3) 0.250000 0.77307(19) 0.0566(7) Uani d 1
H H10 0.570247 0.250000 0.784241 0.068 Uiso calc 1
C C11 0.7595(3) 0.250000 0.84146(18) 0.0571(7) Uani d 1
C C12 0.8995(3) 0.250000 0.82148(19) 0.0620(8) Uani d 1
H H12 0.966318 0.250000 0.867572 0.074 Uiso calc 1
C C13 0.9445(3) 0.250000 0.7374(2) 0.0590(7) Uani d 1
C C14 0.8423(3) 0.250000 0.66939(18) 0.0551(7) Uani d 1
C C15 1.0991(3) 0.250000 0.7198(2) 0.0722(9) Uani d 1
C C16 1.1330(2) 0.0710(4) 0.6677(2) 0.0980(10) Uani d 1
H H16A 1.076649 0.068596 0.614163 0.147 Uiso calc 1
H H16B 1.228999 0.073060 0.655013 0.147 Uiso calc 1
H H16C 1.114737 -0.040681 0.701290 0.147 Uiso calc 1
C C17 1.1899(4) 0.250000 0.8041(3) 0.1274(18) Uani d 1
H H17A 1.285592 0.250000 0.790824 0.191 Uiso d 1
H H17C 1.170713 0.138138 0.837395 0.191 Uiso d 1
C C18 0.7224(3) 0.250000 0.9368(2) 0.0753(9) Uani d 1
C C19 0.7730(5) 0.4303(8) 0.9793(2) 0.176(2) Uani d 1
H H19A 0.734855 0.537623 0.947277 0.264 Uiso calc 1
H H19B 0.744536 0.434730 1.037976 0.264 Uiso calc 1
H H19C 0.872234 0.434730 0.979833 0.264 Uiso calc 1
C C20 0.5646(4) 0.250000 0.9437(3) 0.1131(15) Uani d 1
H H20A 0.525969 0.136290 0.917256 0.170 Uiso d 1
H H20B 0.543785 0.250000 1.003968 0.170 Uiso d 1
Cl Cl1 0.52181(11) 0.250000 0.21237(6) 0.1032(4) Uani d 1
N N1 0.6191(2) 0.250000 0.53735(15) 0.0599(6) Uani d 1
O O1 0.8791(2) 0.250000 0.58613(13) 0.0748(6) Uani d 1
H H1 0.809294 0.250000 0.553116 0.112 Uiso calc 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_
_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
C2 C1 H1A . . 108.6
C2 C1 H1B . . 109.9
H1A C1 H1B . . 109.5
C2 C1 H1B . 4_565 109.91(9)
H1A C1 H1B . 4_565 109.5
H1B C1 H1B . 4_565 109.5
C7 C2 C3 . . 114.6(3)
C7 C2 C1 . . 123.8(3)
C3 C2 C1 . . 121.5(3)
C4 C3 C2 . . 123.1(3)
C4 C3 H3 . . 118.4
C2 C3 H3 . . 118.4
C3 C4 C5 . . 121.1(3)
C3 C4 H4 . . 119.5
C5 C4 H4 . . 119.5
C6 C5 C4 . . 117.6(3)
C6 C5 N1 . . 116.2(2)
C4 C5 N1 . . 126.1(2)
C7 C6 C5 . . 120.0(3)
C7 C6 H6 . . 120.0
C5 C6 H6 . . 120.0
C6 C7 C2 . . 123.6(3)
C6 C7 Cl1 . . 117.2(2)
C2 C7 Cl1 . . 119.2(3)
N1 C8 C9 . . 123.2(2)
N1 C8 H8 . . 118.4
C9 C8 H8 . . 118.4
C10 C9 C14 . . 119.1(3)
C10 C9 C8 . . 119.2(2)
C14 C9 C8 . . 121.7(2)
C11 C10 C9 . . 122.3(2)
C11 C10 H10 . . 118.9
C9 C10 H10 . . 118.9
C10 C11 C12 . . 116.9(2)
C10 C11 C18 . . 123.5(2)
C12 C11 C18 . . 119.6(3)
C13 C12 C11 . . 124.2(3)
C13 C12 H12 . . 117.9
C11 C12 H12 . . 117.9
C12 C13 C14 . . 116.8(2)
C12 C13 C15 . . 121.8(3)
C14 C13 C15 . . 121.5(3)
O1 C14 C13 . . 119.7(2)
O1 C14 C9 . . 119.5(3)
C13 C14 C9 . . 120.8(2)
C17 C15 C16 . . 108.31(19)
C17 C15 C16 . 4_565 108.3(2)
C16 C15 C16 . 4_565 109.7(3)
C17 C15 C13 . . 111.6(3)
C16 C15 C13 . . 109.45(18)
C16 C15 C13 4_565 . 109.45(18)
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
C15 C17 H17A . . 109.4
C15 C17 H17C . . 109.5
H17A C17 H17C . . 109.5
C15 C17 H17C . 4_565 109.48(8)
H17A C17 H17C . 4_565 109.5
H17C C17 H17C . 4_565 109.5
C19 C18 C19 4_565 . 115.8(5)
C19 C18 C11 4_565 . 109.23(18)
C19 C18 C11 . . 109.23(18)
C19 C18 C20 4_565 . 105.8(2)
C19 C18 C20 . . 105.8(2)
C11 C18 C20 . . 110.9(3)
C18 C19 H19A . . 109.5
C18 C19 H19B . . 109.5
H19A C19 H19B . . 109.5
C18 C19 H19C . . 109.5
H19A C19 H19C . . 109.5
H19B C19 H19C . . 109.5
C18 C20 H20A . . 109.5
C18 C20 H20B . . 109.4
H20A C20 H20B . . 108.1
C18 C20 H20A . 4_565 109.49(9)
H20A C20 H20A . 4_565 112.2
H20B C20 H20A . 4_565 108.1
C8 N1 C5 . . 122.8(2)
C14 O1 H1 . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.494(5)
C1 H1A . 0.9600
C1 H1B . 0.9600
C1 H1B 4_565 0.9600
C2 C7 . 1.383(4)
C2 C3 . 1.387(4)
C3 C4 . 1.359(4)
C3 H3 . 0.9300
C4 C5 . 1.383(4)
C4 H4 . 0.9300
C5 C6 . 1.379(4)
C5 N1 . 1.412(4)
C6 C7 . 1.376(4)
C6 H6 . 0.9300
C7 Cl1 . 1.744(3)
C8 N1 . 1.278(4)
C8 C9 . 1.429(4)
C8 H8 . 0.9300
C9 C10 . 1.396(4)
C9 C14 . 1.412(3)
C10 C11 . 1.360(4)
C10 H10 . 0.9300
C11 C12 . 1.407(4)
C11 C18 . 1.530(4)
C12 C13 . 1.389(4)
C12 H12 . 0.9300
C13 C14 . 1.395(4)
C13 C15 . 1.536(4)
C14 O1 . 1.349(3)
C15 C17 . 1.523(5)
C15 C16 . 1.534(3)
C15 C16 4_565 1.534(3)
C16 H16A . 0.9600
C16 H16B . 0.9600
C16 H16C . 0.9600
C17 H17A . 0.9600
C17 H17C . 0.9600
C17 H17C 4_565 0.9600
C18 C19 4_565 1.491(4)
C18 C19 . 1.491(4)
C18 C20 . 1.537(5)
C19 H19A . 0.9600
C19 H19B . 0.9600
C19 H19C . 0.9600
C20 H20A . 0.9600
C20 H20B . 0.9595
C20 H20A 4_565 0.9600
O1 H1 . 0.8200
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 . 0.82 1.84 2.582(3) 149.4 yes
C1 H1B Cg1 2_656 0.96 2.77 3.5072(4) 134 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_4
_geom_torsion
C7 C2 C3 C4 . 0.0000(10)
C1 C2 C3 C4 . 180.0000(10)
C2 C3 C4 C5 . 0.0000(10)
C3 C4 C5 C6 . 0.0000(10)
C3 C4 C5 N1 . 180.0000(10)
C4 C5 C6 C7 . 0.0000(10)
N1 C5 C6 C7 . 180.0000(10)
C5 C6 C7 C2 . 0.0000(10)
C5 C6 C7 Cl1 . 180.0000(10)
C3 C2 C7 C6 . 0.0000(10)
C1 C2 C7 C6 . 180.000000
C3 C2 C7 Cl1 . 180.000000
C1 C2 C7 Cl1 . 0.0000(10)
N1 C8 C9 C10 . 180.0000(10)
N1 C8 C9 C14 . 0.0000(10)
C14 C9 C10 C11 . 0.0000(10)
C8 C9 C10 C11 . 180.0000(10)
C9 C10 C11 C12 . 0.0000(10)
C9 C10 C11 C18 . 180.0000(10)
C10 C11 C12 C13 . 0.000(2)
C18 C11 C12 C13 . 180.0000(10)
C11 C12 C13 C14 . 0.0000(10)
C11 C12 C13 C15 . 180.0000(10)
C12 C13 C14 O1 . 180.0000(10)
C15 C13 C14 O1 . 0.0000(10)
C12 C13 C14 C9 . 0.0000(10)
C15 C13 C14 C9 . 180.0000(10)
C10 C9 C14 O1 . 180.0000(10)
C8 C9 C14 O1 . 0.0000(10)
C10 C9 C14 C13 . 0.0000(10)
C8 C9 C14 C13 . 180.0000(10)
C12 C13 C15 C17 . 0.0000(10)
C14 C13 C15 C17 . 180.0000(10)
C12 C13 C15 C16 . 119.9(2)
C14 C13 C15 C16 . -60.1(2)
C12 C13 C15 C16 4_565 -119.9(2)
C14 C13 C15 C16 4_565 60.1(2)
C10 C11 C18 C19 4_565 116.2(3)
C12 C11 C18 C19 4_565 -63.8(3)
C10 C11 C18 C19 . -116.2(3)
C12 C11 C18 C19 . 63.8(3)
C10 C11 C18 C20 . 0.000(2)
C12 C11 C18 C20 . 180.0000(10)
C9 C8 N1 C5 . 180.0000(10)
C6 C5 N1 C8 . 180.0000(10)
C4 C5 N1 C8 . 0.0000(10)

_cod_database_fobs_code 2242763
