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#$Date: 2023-05-22 12:24:03 +0300 (Mon, 22 May 2023) $
#$Revision: 283936 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/72/8107243.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8107243
loop_
_publ_author_name
'Zhao, Ji-Xing'
'Wang, Xiao-Jun'
_publ_section_title
;
 Synthesis and crystal structure of
 (E)-1-(4-(((E)-3-(tert-butyl)-2-hydroxybenzylidene)amino)phenyl)ethan-1-one
 O-methyl oxime, C20H24N2O2
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              885
_journal_page_last               887
_journal_paper_doi               10.1515/ncrs-2022-0282
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C20 H24 N2 O2'
_chemical_formula_sum            'C20 H24 N2 O2'
_chemical_formula_weight         324.41
_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   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 97.9330(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5088(4)
_cell_length_b                   17.4849(6)
_cell_length_c                   7.1398(2)
_cell_measurement_reflns_used    6152
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      26.67
_cell_measurement_theta_min      2.33
_cell_volume                     1793.93(9)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            22136
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.740
_diffrn_reflns_theta_min         2.330
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0725 before and 0.0511 after correction. The Ratio of minimum to maximum transmission is 0.8987. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3804
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0561
_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)+(0.0655P)²+0.9421P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1431
_refine_ls_wR_factor_ref         0.1596
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2931
_reflns_number_total             3804
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0282_suppl.cif
_cod_data_source_block           11
_cod_database_code               8107243
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid bond restraints
 N2, C18
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C11(H11), C13(H13), C14(H14), C16(H16), C17(H17)
3.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C19(H19A,H19B,H19C),
 C20(H20A,H20B,H20C)
3.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.74657(10) 0.40657(9) 0.41679(18) 0.0454(4) Uani 1 1 d . . . . .
H1 H 0.697049 0.403520 0.464968 0.068 Uiso 1 1 calc R U . . .
O2 O 0.22386(11) 0.39697(10) 1.1559(2) 0.0568(4) Uani 1 1 d . . . . .
N1 N 0.57176(11) 0.38314(9) 0.4357(2) 0.0372(4) Uani 1 1 d . . . . .
N2 N 0.29675(12) 0.40468(10) 1.0486(2) 0.0455(4) Uani 1 1 d . U . . .
C1 C 0.64164(12) 0.35625(10) 0.1582(2) 0.0325(4) Uani 1 1 d . . . . .
C2 C 0.73235(13) 0.37831(10) 0.2389(2) 0.0341(4) Uani 1 1 d . . . . .
C3 C 0.80811(13) 0.37129(10) 0.1365(3) 0.0361(4) Uani 1 1 d . . . . .
C4 C 0.78927(14) 0.34173(11) -0.0450(3) 0.0397(4) Uani 1 1 d . . . . .
H4 H 0.839429 0.336261 -0.116556 0.048 Uiso 1 1 calc R U . . .
C5 C 0.70087(14) 0.31965(11) -0.1278(3) 0.0394(4) Uani 1 1 d . . . . .
H5 H 0.691262 0.299846 -0.252918 0.047 Uiso 1 1 calc R U . . .
C6 C 0.62780(13) 0.32693(10) -0.0260(2) 0.0351(4) Uani 1 1 d . . . . .
H6 H 0.567140 0.311925 -0.081123 0.042 Uiso 1 1 calc R U . . .
C7 C 0.90697(14) 0.39582(12) 0.2225(3) 0.0447(5) Uani 1 1 d . . . . .
C8 C 0.97701(16) 0.38147(17) 0.0841(4) 0.0671(7) Uani 1 1 d . . . . .
H8A H 0.980077 0.326557 0.058200 0.101 Uiso 1 1 calc R U . . .
H8B H 1.038589 0.399738 0.139828 0.101 Uiso 1 1 calc R U . . .
H8C H 0.957158 0.408951 -0.034239 0.101 Uiso 1 1 calc R U . . .
C9 C 0.93871(17) 0.35127(16) 0.4048(4) 0.0708(8) Uani 1 1 d . . . . .
H9A H 0.895691 0.361136 0.496432 0.106 Uiso 1 1 calc R U . . .
H9B H 1.001466 0.367753 0.457863 0.106 Uiso 1 1 calc R U . . .
H9C H 0.939287 0.296427 0.376640 0.106 Uiso 1 1 calc R U . . .
C10 C 0.90749(16) 0.48186(13) 0.2625(3) 0.0517(5) Uani 1 1 d . . . . .
H10A H 0.887671 0.509639 0.144589 0.078 Uiso 1 1 calc R U . . .
H10B H 0.970507 0.497936 0.314869 0.078 Uiso 1 1 calc R U . . .
H10C H 0.864627 0.493076 0.353633 0.078 Uiso 1 1 calc R U . . .
C11 C 0.56341(13) 0.35987(10) 0.2632(3) 0.0350(4) Uani 1 1 d . . . . .
H11 H 0.503809 0.344552 0.202850 0.042 Uiso 1 1 calc R U . . .
C12 C 0.49559(13) 0.37883(11) 0.5395(2) 0.0360(4) Uani 1 1 d . . . . .
C13 C 0.43126(13) 0.31923(11) 0.5175(3) 0.0382(4) Uani 1 1 d . . . . .
H13 H 0.435680 0.280902 0.424799 0.046 Uiso 1 1 calc R U . . .
C14 C 0.36091(13) 0.31561(11) 0.6300(3) 0.0385(4) Uani 1 1 d . . . . .
H14 H 0.317534 0.274644 0.613635 0.046 Uiso 1 1 calc R U . . .
C15 C 0.35271(13) 0.37112(11) 0.7668(2) 0.0366(4) Uani 1 1 d . . . . .
C16 C 0.41728(14) 0.43105(11) 0.7868(3) 0.0388(4) Uani 1 1 d . . . . .
H16 H 0.411939 0.470133 0.877078 0.047 Uiso 1 1 calc R U . . .
C17 C 0.48842(14) 0.43432(11) 0.6777(3) 0.0387(4) Uani 1 1 d . . . . .
H17 H 0.532832 0.474479 0.696513 0.046 Uiso 1 1 calc R U . . .
C18 C 0.27859(14) 0.36598(12) 0.8893(3) 0.0411(4) Uani 1 1 d . U . . .
C19 C 0.19332(15) 0.31972(14) 0.8270(3) 0.0534(6) Uani 1 1 d . . . . .
H19A H 0.209726 0.265342 0.827611 0.080 Uiso 1 1 calc R U . . .
H19B H 0.166720 0.335030 0.698833 0.080 Uiso 1 1 calc R U . . .
H19C H 0.147561 0.328437 0.913669 0.080 Uiso 1 1 calc R U . . .
C20 C 0.23956(17) 0.45378(15) 1.3014(3) 0.0563(6) Uani 1 1 d . . . . .
H20A H 0.233895 0.504812 1.244175 0.084 Uiso 1 1 calc R U . . .
H20B H 0.302157 0.447435 1.371120 0.084 Uiso 1 1 calc R U . . .
H20C H 0.193350 0.447962 1.388361 0.084 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 O1 H1 109.5 . .
N2 O2 C20 105.93(16) . .
C11 N1 C12 120.50(16) . .
C18 N2 O2 110.35(17) . .
C2 C1 C11 121.97(16) . .
C6 C1 C2 119.14(16) . .
C6 C1 C11 118.84(16) . .
O1 C2 C1 119.65(16) . .
O1 C2 C3 119.42(16) . .
C3 C2 C1 120.93(16) . .
C2 C3 C7 121.31(16) . .
C4 C3 C2 116.78(16) . .
C4 C3 C7 121.91(17) . .
C3 C4 H4 118.2 . .
C3 C4 C5 123.52(18) . .
C5 C4 H4 118.2 . .
C4 C5 H5 120.5 . .
C6 C5 C4 118.93(17) . .
C6 C5 H5 120.5 . .
C1 C6 H6 119.6 . .
C5 C6 C1 120.71(17) . .
C5 C6 H6 119.6 . .
C8 C7 C3 111.17(17) . .
C9 C7 C3 110.55(17) . .
C9 C7 C8 108.4(2) . .
C10 C7 C3 109.15(17) . .
C10 C7 C8 107.13(18) . .
C10 C7 C9 110.3(2) . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8B 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C7 C9 H9A 109.5 . .
C7 C9 H9B 109.5 . .
C7 C9 H9C 109.5 . .
H9A C9 H9B 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C7 C10 H10A 109.5 . .
C7 C10 H10B 109.5 . .
C7 C10 H10C 109.5 . .
H10A C10 H10B 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
N1 C11 C1 122.24(17) . .
N1 C11 H11 118.9 . .
C1 C11 H11 118.9 . .
C13 C12 N1 122.67(16) . .
C13 C12 C17 119.02(17) . .
C17 C12 N1 118.20(17) . .
C12 C13 H13 119.9 . .
C14 C13 C12 120.29(17) . .
C14 C13 H13 119.9 . .
C13 C14 H14 119.5 . .
C13 C14 C15 121.06(18) . .
C15 C14 H14 119.5 . .
C14 C15 C16 118.16(17) . .
C14 C15 C18 120.74(18) . .
C16 C15 C18 121.09(17) . .
C15 C16 H16 119.4 . .
C17 C16 C15 121.12(17) . .
C17 C16 H16 119.4 . .
C12 C17 H17 119.8 . .
C16 C17 C12 120.32(18) . .
C16 C17 H17 119.8 . .
N2 C18 C15 113.81(18) . .
N2 C18 C19 126.40(18) . .
C15 C18 C19 119.80(17) . .
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 . .
O2 C20 H20A 109.5 . .
O2 C20 H20B 109.5 . .
O2 C20 H20C 109.5 . .
H20A C20 H20B 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 H1 0.8400 .
O1 C2 1.352(2) .
O2 N2 1.395(2) .
O2 C20 1.433(3) .
N1 C11 1.286(2) .
N1 C12 1.415(2) .
N2 C18 1.319(3) .
C1 C2 1.415(2) .
C1 C6 1.400(2) .
C1 C11 1.445(2) .
C2 C3 1.407(3) .
C3 C4 1.387(3) .
C3 C7 1.541(3) .
C4 H4 0.9500 .
C4 C5 1.391(3) .
C5 H5 0.9500 .
C5 C6 1.372(3) .
C6 H6 0.9500 .
C7 C8 1.533(3) .
C7 C9 1.532(3) .
C7 C10 1.531(3) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 H11 0.9500 .
C12 C13 1.393(3) .
C12 C17 1.398(3) .
C13 H13 0.9500 .
C13 C14 1.385(3) .
C14 H14 0.9500 .
C14 C15 1.394(3) .
C15 C16 1.400(3) .
C15 C18 1.479(3) .
C16 H16 0.9500 .
C16 C17 1.377(3) .
C17 H17 0.9500 .
C18 C19 1.494(3) .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O1 C2 C3 C4 179.80(17) . . . .
O1 C2 C3 C7 -0.5(3) . . . .
O2 N2 C18 C15 -179.97(15) . . . .
O2 N2 C18 C19 -0.1(3) . . . .
N1 C12 C13 C14 176.50(16) . . . .
N1 C12 C17 C16 -177.83(16) . . . .
C1 C2 C3 C4 -0.2(3) . . . .
C1 C2 C3 C7 179.46(17) . . . .
C2 C1 C6 C5 -0.1(3) . . . .
C2 C1 C11 N1 -0.2(3) . . . .
C2 C3 C4 C5 0.3(3) . . . .
C2 C3 C7 C8 179.26(19) . . . .
C2 C3 C7 C9 58.8(3) . . . .
C2 C3 C7 C10 -62.8(2) . . . .
C3 C4 C5 C6 -0.2(3) . . . .
C4 C3 C7 C8 -1.1(3) . . . .
C4 C3 C7 C9 -121.6(2) . . . .
C4 C3 C7 C10 116.9(2) . . . .
C4 C5 C6 C1 0.1(3) . . . .
C6 C1 C2 O1 -179.89(16) . . . .
C6 C1 C2 C3 0.1(3) . . . .
C6 C1 C11 N1 177.06(17) . . . .
C7 C3 C4 C5 -179.40(18) . . . .
C11 N1 C12 C13 35.3(3) . . . .
C11 N1 C12 C17 -148.70(18) . . . .
C11 C1 C2 O1 -2.7(3) . . . .
C11 C1 C2 C3 177.34(16) . . . .
C11 C1 C6 C5 -177.38(16) . . . .
C12 N1 C11 C1 -173.80(16) . . . .
C12 C13 C14 C15 0.1(3) . . . .
C13 C12 C17 C16 -1.7(3) . . . .
C13 C14 C15 C16 0.4(3) . . . .
C13 C14 C15 C18 -178.68(17) . . . .
C14 C15 C16 C17 -1.6(3) . . . .
C14 C15 C18 N2 158.09(18) . . . .
C14 C15 C18 C19 -21.8(3) . . . .
C15 C16 C17 C12 2.2(3) . . . .
C16 C15 C18 N2 -21.0(3) . . . .
C16 C15 C18 C19 159.14(19) . . . .
C17 C12 C13 C14 0.5(3) . . . .
C18 C15 C16 C17 177.51(17) . . . .
C20 O2 N2 C18 -167.09(18) . . . .
