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#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/65/1556502.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_1556502
loop_
_publ_author_name
'Gietz, T.'
'Boere, R.T.'
_publ_section_title
;
 Backbone-Substituted beta-Ketoimines and Ketoiminate Clusters: Transoid
 Li2O2 Squares and D2-Symmetric Li4O4 Cubanes. Synthesis, Crystallography
 and DFT Calculations
;
_journal_name_full               Inorganics
_journal_page_first              30
_journal_paper_doi               10.3390/inorganics5020030
_journal_volume                  5
_journal_year                    2017
_chemical_formula_moiety         'C15 H21 N O'
_chemical_formula_sum            'C15 H21 N O'
_chemical_formula_weight         231.33
_chemical_name_common            'Mes KetoImine'
_chemical_name_systematic
; 
 2-(2,4,6-trimethylphenylamino)-3-methylpent-2-en-4-one 
;
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 107.5430(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.8762(17)
_cell_length_b                   8.0097(7)
_cell_length_c                   19.0037(17)
_cell_measurement_reflns_used    8768
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.21
_cell_measurement_theta_min      2.25
_cell_volume                     2739.6(4)
_computing_cell_refinement       'APEX2 (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2006)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  'IUCr publCIF (Westrip, 2007)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2003)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Bruker ApexII CCD area detector
;
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19053
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.25
_diffrn_source_type              'Bruker D8'
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_correction_T_min  0.9169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS (Sheldrick, 2004)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3153
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0673P)²+1.8094P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1402
_reflns_number_gt                2517
_reflns_number_total             3153
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            Inorganics-2017-5-30.cif
_cod_data_source_block           Ligand_1d
_cod_original_sg_symbol_Hall     -C2yc
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1556502
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.18446(6) 0.66828(16) 0.35565(6) 0.0492(3) Uani 1 1 d . . .
N1 N 0.07564(6) 0.82481(15) 0.38213(6) 0.0327(3) Uani 1 1 d . . .
H1 H 0.1061(9) 0.803(2) 0.3549(9) 0.039 Uiso 1 1 d . . .
C1 C 0.25911(8) 0.4726(2) 0.43818(10) 0.0463(4) Uani 1 1 d . . .
H1A H 0.2821 0.4638 0.3984 0.056 Uiso 1 1 calc R . .
H1B H 0.2394 0.3634 0.4463 0.056 Uiso 1 1 calc R . .
H1C H 0.2964 0.5090 0.4836 0.056 Uiso 1 1 calc R . .
C2 C 0.19636(7) 0.59850(18) 0.41688(8) 0.0345(3) Uani 1 1 d . . .
C3 C 0.15364(7) 0.63080(17) 0.46609(7) 0.0325(3) Uani 1 1 d . . .
C4 C 0.09360(7) 0.73928(16) 0.44607(7) 0.0308(3) Uani 1 1 d . . .
C5 C 0.04647(9) 0.7708(2) 0.49604(8) 0.0466(4) Uani 1 1 d . . .
H5A H 0.0764 0.8265 0.5411 0.056 Uiso 1 1 calc R . .
H5B H 0.0280 0.6642 0.5089 0.056 Uiso 1 1 calc R . .
H5C H 0.0043 0.8420 0.4706 0.056 Uiso 1 1 calc R . .
C6 C 0.17415(10) 0.5435(2) 0.54056(9) 0.0480(4) Uani 1 1 d . . .
H6A H 0.1532 0.6055 0.5741 0.058 Uiso 1 1 calc R . .
H6B H 0.2284 0.5391 0.5613 0.058 Uiso 1 1 calc R . .
H6C H 0.1541 0.4298 0.5343 0.058 Uiso 1 1 calc R . .
C7 C -0.06220(9) 0.64703(19) 0.31823(10) 0.0464(4) Uani 1 1 d . . .
H7A H -0.0611 0.6068 0.3672 0.056 Uiso 1 1 calc R . .
H7B H -0.0196 0.6013 0.3052 0.056 Uiso 1 1 calc R . .
H7C H -0.1084 0.6108 0.2818 0.056 Uiso 1 1 calc R . .
C8 C -0.05821(7) 0.83546(16) 0.31896(7) 0.0308(3) Uani 1 1 d . . .
C9 C 0.00894(7) 0.91879(16) 0.35089(7) 0.0263(3) Uani 1 1 d . . .
C10 C 0.01253(7) 1.09295(16) 0.35016(7) 0.0270(3) Uani 1 1 d . . .
C11 C 0.08431(8) 1.1843(2) 0.38545(8) 0.0398(3) Uani 1 1 d . . .
H11A H 0.0786 1.3020 0.3707 0.048 Uiso 1 1 calc R . .
H11B H 0.1242 1.1341 0.3693 0.048 Uiso 1 1 calc R . .
H11C H 0.0968 1.1761 0.4393 0.048 Uiso 1 1 calc R . .
C12 C -0.05251(7) 1.18156(16) 0.31703(7) 0.0295(3) Uani 1 1 d . . .
H12 H -0.0505 1.3000 0.3157 0.035 Uiso 1 1 calc R . .
C13 C -0.12015(7) 1.10261(17) 0.28589(7) 0.0301(3) Uani 1 1 d . . .
C14 C -0.19049(8) 1.2011(2) 0.25194(9) 0.0444(4) Uani 1 1 d . . .
H14A H -0.2192 1.2079 0.2870 0.053 Uiso 1 1 calc R . .
H14B H -0.2202 1.1454 0.2068 0.053 Uiso 1 1 calc R . .
H14C H -0.1776 1.3140 0.2400 0.053 Uiso 1 1 calc R . .
C15 C -0.12178(7) 0.92904(18) 0.28735(7) 0.0323(3) Uani 1 1 d . . .
H15 H -0.1676 0.8730 0.2662 0.039 Uiso 1 1 calc R . .
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
C4 N1 C9 126.29(11) . .
C4 N1 H1 113.0(10) . .
C9 N1 H1 119.8(10) . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
O1 C2 C3 123.35(12) . .
O1 C2 C1 116.96(13) . .
C3 C2 C1 119.69(13) . .
C4 C3 C2 120.59(12) . .
C4 C3 C6 120.08(13) . .
C2 C3 C6 119.33(12) . .
N1 C4 C3 121.93(12) . .
N1 C4 C5 116.63(12) . .
C3 C4 C5 121.41(12) . .
C4 C5 H5A 109.5 . .
C4 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C4 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C3 C6 H6A 109.5 . .
C3 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C3 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C8 C7 H7A 109.5 . .
C8 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C8 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C15 C8 C9 118.82(12) . .
C15 C8 C7 120.07(12) . .
C9 C8 C7 121.11(12) . .
C10 C9 C8 120.84(11) . .
C10 C9 N1 119.30(11) . .
C8 C9 N1 119.81(12) . .
C12 C10 C9 118.32(11) . .
C12 C10 C11 120.35(12) . .
C9 C10 C11 121.33(12) . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C13 C12 C10 122.19(12) . .
C13 C12 H12 118.9 . .
C10 C12 H12 118.9 . .
C12 C13 C15 118.05(12) . .
C12 C13 C14 121.40(13) . .
C15 C13 C14 120.55(13) . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C8 C15 C13 121.78(12) . .
C8 C15 H15 119.1 . .
C13 C15 H15 119.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.2489(17) .
N1 C4 1.3462(17) .
N1 C9 1.4331(16) .
N1 H1 0.898(17) .
C1 C2 1.5149(19) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 C3 1.430(2) .
C3 C4 1.3872(19) .
C3 C6 1.5202(19) .
C4 C5 1.505(2) .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 C8 1.5110(19) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 C15 1.3886(18) .
C8 C9 1.3987(18) .
C9 C10 1.3969(18) .
C10 C12 1.3933(17) .
C10 C11 1.5077(17) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 C13 1.3873(18) .
C12 H12 0.9500 .
C13 C15 1.391(2) .
C13 C14 1.5119(18) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.898(17) 1.829(17) 2.5823(15) 140.0(15) .
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 2.6(2) . . . .
C1 C2 C3 C4 -176.73(13) . . . .
O1 C2 C3 C6 -178.02(15) . . . .
C1 C2 C3 C6 2.6(2) . . . .
C9 N1 C4 C3 169.57(13) . . . .
C9 N1 C4 C5 -12.1(2) . . . .
C2 C3 C4 N1 -3.7(2) . . . .
C6 C3 C4 N1 176.93(13) . . . .
C2 C3 C4 C5 178.04(14) . . . .
C6 C3 C4 C5 -1.3(2) . . . .
C15 C8 C9 C10 -0.98(18) . . . .
C7 C8 C9 C10 178.79(13) . . . .
C15 C8 C9 N1 -178.38(11) . . . .
C7 C8 C9 N1 1.39(19) . . . .
C4 N1 C9 C10 108.91(16) . . . .
C4 N1 C9 C8 -73.65(18) . . . .
C8 C9 C10 C12 0.21(18) . . . .
N1 C9 C10 C12 177.62(11) . . . .
C8 C9 C10 C11 179.02(12) . . . .
N1 C9 C10 C11 -3.57(18) . . . .
C9 C10 C12 C13 0.79(18) . . . .
C11 C10 C12 C13 -178.03(12) . . . .
C10 C12 C13 C15 -0.97(19) . . . .
C10 C12 C13 C14 178.40(12) . . . .
C9 C8 C15 C13 0.79(19) . . . .
C7 C8 C15 C13 -178.97(13) . . . .
C12 C13 C15 C8 0.2(2) . . . .
C14 C13 C15 C8 -179.21(12) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168305821
