#------------------------------------------------------------------------------
#$Date: 2019-12-11 12:06:29 +0200 (Wed, 11 Dec 2019) $
#$Revision: 244994 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/65/1556504.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_1556504
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         'C36 H52 Li2 N2 O4'
_chemical_formula_sum            'C36 H52 Li2 N2 O4'
_chemical_formula_weight         590.68
_chemical_name_systematic
; 
 lithio 2-(2,4,6-trimethylphenylamino)pent-2-en-4-one
 dimer thf adduct
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 103.8550(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.0148(5)
_cell_length_b                   15.0628(9)
_cell_length_c                   14.5918(9)
_cell_measurement_reflns_used    5948
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      22.61
_cell_measurement_theta_min      2.62
_cell_volume                     1710.35(18)
_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 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19537
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.97
_diffrn_source_type              'Bruker D8'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_correction_T_min  0.8956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS (Sheldrick, 2004)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3919
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0495
_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)+(0.0608P)²+0.6606P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1409
_reflns_number_gt                2722
_reflns_number_total             3919
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            Inorganics-2017-5-30.cif
_cod_data_source_block           Complex_2b
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1556504
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.57847(16) 0.02247(8) -0.07259(8) 0.0334(3) Uani 1 1 d . . .
O2 O 0.67390(16) 0.13984(8) 0.12671(9) 0.0401(3) Uani 1 1 d . . .
N1 N 0.35785(18) 0.17489(9) -0.06582(9) 0.0293(3) Uani 1 1 d . . .
C1 C 0.6509(3) -0.00406(13) -0.21839(14) 0.0446(5) Uani 1 1 d . . .
H1A H 0.7750 0.0029 -0.1930 0.053 Uiso 1 1 calc R . .
H1B H 0.6193 0.0181 -0.2834 0.053 Uiso 1 1 calc R . .
H1C H 0.6203 -0.0670 -0.2176 0.053 Uiso 1 1 calc R . .
C2 C 0.5555(2) 0.04816(11) -0.15852(12) 0.0311(4) Uani 1 1 d . . .
C3 C 0.4523(2) 0.11762(12) -0.19924(12) 0.0353(4) Uani 1 1 d . . .
H3 H 0.4461 0.1280 -0.2642 0.042 Uiso 1 1 calc R . .
C4 C 0.3532(2) 0.17618(11) -0.15587(12) 0.0320(4) Uani 1 1 d . . .
C5 C 0.2379(3) 0.24078(13) -0.22174(13) 0.0436(5) Uani 1 1 d . . .
H5A H 0.1174 0.2274 -0.2238 0.052 Uiso 1 1 calc R . .
H5B H 0.2574 0.2352 -0.2853 0.052 Uiso 1 1 calc R . .
H5C H 0.2643 0.3015 -0.1988 0.052 Uiso 1 1 calc R . .
C6 C 0.2530(2) 0.23588(10) -0.03007(11) 0.0280(4) Uani 1 1 d . . .
C7 C 0.0947(2) 0.20700(11) -0.01576(11) 0.0301(4) Uani 1 1 d . . .
C8 C 0.0307(3) 0.11487(12) -0.04520(14) 0.0404(4) Uani 1 1 d . . .
H8A H -0.0802 0.1054 -0.0295 0.049 Uiso 1 1 calc R . .
H8B H 0.1139 0.0711 -0.0119 0.049 Uiso 1 1 calc R . .
H8C H 0.0167 0.1081 -0.1134 0.049 Uiso 1 1 calc R . .
C9 C -0.0020(2) 0.26468(11) 0.02468(12) 0.0335(4) Uani 1 1 d . . .
H9 H -0.1097 0.2452 0.0336 0.040 Uiso 1 1 calc R . .
C10 C 0.0539(2) 0.35027(11) 0.05263(13) 0.0360(4) Uani 1 1 d . . .
C11 C -0.0496(3) 0.41046(14) 0.10077(17) 0.0536(6) Uani 1 1 d . . .
H11A H 0.0072 0.4151 0.1680 0.064 Uiso 1 1 calc R . .
H11B H -0.1651 0.3858 0.0937 0.064 Uiso 1 1 calc R . .
H11C H -0.0579 0.4695 0.0719 0.064 Uiso 1 1 calc R . .
C12 C 0.2101(2) 0.37713(11) 0.03787(12) 0.0356(4) Uani 1 1 d . . .
H12 H 0.2500 0.4353 0.0566 0.043 Uiso 1 1 calc R . .
C13 C 0.3113(2) 0.32228(11) -0.00330(12) 0.0309(4) Uani 1 1 d . . .
C14 C 0.4783(2) 0.35564(13) -0.01987(14) 0.0423(5) Uani 1 1 d . . .
H14A H 0.4592 0.3788 -0.0843 0.051 Uiso 1 1 calc R . .
H14B H 0.5614 0.3068 -0.0114 0.051 Uiso 1 1 calc R . .
H14C H 0.5232 0.4031 0.0253 0.051 Uiso 1 1 calc R . .
C15 C 0.6411(3) 0.21352(14) 0.18111(14) 0.0518(6) Uani 1 1 d . . .
H15A H 0.5171 0.2164 0.1795 0.062 Uiso 1 1 calc R . .
H15B H 0.6740 0.2694 0.1543 0.062 Uiso 1 1 calc R . .
C16 C 0.7411(3) 0.20310(17) 0.27875(15) 0.0639(7) Uani 1 1 d . . .
H16A H 0.6654 0.2068 0.3232 0.077 Uiso 1 1 calc R . .
H16B H 0.8302 0.2498 0.2951 0.077 Uiso 1 1 calc R . .
C17 C 0.8226(3) 0.11285(15) 0.28300(15) 0.0552(6) Uani 1 1 d . . .
H17A H 0.7557 0.0684 0.3092 0.066 Uiso 1 1 calc R . .
H17B H 0.9418 0.1140 0.3222 0.066 Uiso 1 1 calc R . .
C18 C 0.8195(3) 0.09247(14) 0.18158(15) 0.0487(5) Uani 1 1 d . . .
H18A H 0.9269 0.1128 0.1660 0.058 Uiso 1 1 calc R . .
H18B H 0.8067 0.0279 0.1694 0.058 Uiso 1 1 calc R . .
Li1 Li 0.5002(4) 0.08479(19) 0.02133(19) 0.0326(6) Uani 1 1 d . . .
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'
Li Li -0.0003 0.0001 '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 Li1 124.39(14) . .
C2 O1 Li1 129.92(13) . 3_655
Li1 O1 Li1 86.52(13) . 3_655
C15 O2 C18 108.05(14) . .
C15 O2 Li1 124.50(14) . .
C18 O2 Li1 123.22(14) . .
C4 N1 C6 118.78(14) . .
C4 N1 Li1 121.33(14) . .
C6 N1 Li1 119.81(13) . .
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 125.57(16) . .
O1 C2 C1 115.71(16) . .
C3 C2 C1 118.72(16) . .
C2 C3 C4 128.08(16) . .
C2 C3 H3 116.0 . .
C4 C3 H3 116.0 . .
N1 C4 C3 123.40(16) . .
N1 C4 C5 120.89(16) . .
C3 C4 C5 115.70(15) . .
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 . .
C7 C6 C13 119.83(15) . .
C7 C6 N1 119.20(14) . .
C13 C6 N1 120.84(15) . .
C9 C7 C6 119.10(15) . .
C9 C7 C8 120.81(16) . .
C6 C7 C8 120.09(16) . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C7 C9 C10 122.11(17) . .
C7 C9 H9 118.9 . .
C10 C9 H9 118.9 . .
C12 C10 C9 117.71(17) . .
C12 C10 C11 121.05(17) . .
C9 C10 C11 121.20(18) . .
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 . .
C10 C12 C13 122.51(16) . .
C10 C12 H12 118.7 . .
C13 C12 H12 118.7 . .
C12 C13 C6 118.73(16) . .
C12 C13 C14 120.32(15) . .
C6 C13 C14 120.95(16) . .
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 . .
O2 C15 C16 109.09(17) . .
O2 C15 H15A 109.9 . .
C16 C15 H15A 109.9 . .
O2 C15 H15B 109.9 . .
C16 C15 H15B 109.9 . .
H15A C15 H15B 108.3 . .
C15 C16 C17 105.53(18) . .
C15 C16 H16A 110.6 . .
C17 C16 H16A 110.6 . .
C15 C16 H16B 110.6 . .
C17 C16 H16B 110.6 . .
H16A C16 H16B 108.8 . .
C16 C17 C18 103.84(17) . .
C16 C17 H17A 111.0 . .
C18 C17 H17A 111.0 . .
C16 C17 H17B 111.0 . .
C18 C17 H17B 111.0 . .
H17A C17 H17B 109.0 . .
O2 C18 C17 105.44(16) . .
O2 C18 H18A 110.7 . .
C17 C18 H18A 110.7 . .
O2 C18 H18B 110.7 . .
C17 C18 H18B 110.7 . .
H18A C18 H18B 108.8 . .
O1 Li1 O1 93.48(13) . 3_655
O1 Li1 O2 118.37(16) . .
O1 Li1 O2 106.23(13) 3_655 .
O1 Li1 N1 96.49(13) . .
O1 Li1 N1 127.90(16) 3_655 .
O2 Li1 N1 113.09(14) . .
O1 Li1 Li1 47.69(10) . 3_655
O1 Li1 Li1 45.79(10) 3_655 3_655
O2 Li1 Li1 123.25(18) . 3_655
N1 Li1 Li1 122.43(17) . 3_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.283(2) .
O1 Li1 1.888(3) .
O1 Li1 1.948(3) 3_655
O2 C15 1.425(2) .
O2 C18 1.437(2) .
O2 Li1 1.991(3) .
N1 C4 1.306(2) .
N1 C6 1.425(2) .
N1 Li1 2.016(3) .
C1 C2 1.512(2) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 C3 1.377(2) .
C3 C4 1.432(2) .
C3 H3 0.9500 .
C4 C5 1.517(2) .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 C7 1.404(2) .
C6 C13 1.406(2) .
C7 C9 1.386(2) .
C7 C8 1.506(2) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C10 1.393(2) .
C9 H9 0.9500 .
C10 C12 1.381(3) .
C10 C11 1.510(3) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 C13 1.391(3) .
C12 H12 0.9500 .
C13 C14 1.502(2) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 C16 1.466(3) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.503(3) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 C18 1.506(3) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
Li1 O1 1.948(3) 3_655
Li1 Li1 2.629(6) 3_655
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
Li1 O1 C2 C3 -9.1(3) . . . .
Li1 O1 C2 C3 109.3(2) 3_655 . . .
Li1 O1 C2 C1 171.24(16) . . . .
Li1 O1 C2 C1 -70.3(2) 3_655 . . .
O1 C2 C3 C4 1.4(3) . . . .
C1 C2 C3 C4 -179.04(17) . . . .
C6 N1 C4 C3 -179.64(15) . . . .
Li1 N1 C4 C3 -2.8(2) . . . .
C6 N1 C4 C5 -0.4(2) . . . .
Li1 N1 C4 C5 176.46(16) . . . .
C2 C3 C4 N1 5.2(3) . . . .
C2 C3 C4 C5 -174.07(18) . . . .
C4 N1 C6 C7 98.31(18) . . . .
Li1 N1 C6 C7 -78.60(19) . . . .
C4 N1 C6 C13 -85.93(19) . . . .
Li1 N1 C6 C13 97.16(18) . . . .
C13 C6 C7 C9 0.1(2) . . . .
N1 C6 C7 C9 175.88(14) . . . .
C13 C6 C7 C8 179.37(15) . . . .
N1 C6 C7 C8 -4.8(2) . . . .
C6 C7 C9 C10 -0.7(2) . . . .
C8 C7 C9 C10 180.00(16) . . . .
C7 C9 C10 C12 0.7(3) . . . .
C7 C9 C10 C11 -177.05(17) . . . .
C9 C10 C12 C13 0.0(3) . . . .
C11 C10 C12 C13 177.75(17) . . . .
C10 C12 C13 C6 -0.6(3) . . . .
C10 C12 C13 C14 178.50(16) . . . .
C7 C6 C13 C12 0.6(2) . . . .
N1 C6 C13 C12 -175.15(14) . . . .
C7 C6 C13 C14 -178.56(15) . . . .
N1 C6 C13 C14 5.7(2) . . . .
C18 O2 C15 C16 -12.3(3) . . . .
Li1 O2 C15 C16 145.13(19) . . . .
O2 C15 C16 C17 -6.1(3) . . . .
C15 C16 C17 C18 21.0(3) . . . .
C15 O2 C18 C17 25.5(2) . . . .
Li1 O2 C18 C17 -132.21(18) . . . .
C16 C17 C18 O2 -28.5(2) . . . .
C2 O1 Li1 O1 137.52(16) . . . 3_655
Li1 O1 Li1 O1 0.0 3_655 . . 3_655
C2 O1 Li1 O2 -111.92(18) . . . .
Li1 O1 Li1 O2 110.56(19) 3_655 . . .
C2 O1 Li1 N1 8.7(2) . . . .
Li1 O1 Li1 N1 -128.78(17) 3_655 . . .
C2 O1 Li1 Li1 137.52(16) . . . 3_655
C15 O2 Li1 O1 155.53(17) . . . .
C18 O2 Li1 O1 -50.4(2) . . . .
C15 O2 Li1 O1 -101.22(19) . . . 3_655
C18 O2 Li1 O1 52.9(2) . . . 3_655
C15 O2 Li1 N1 43.8(2) . . . .
C18 O2 Li1 N1 -162.07(16) . . . .
C15 O2 Li1 Li1 -148.6(2) . . . 3_655
C18 O2 Li1 Li1 5.5(3) . . . 3_655
C4 N1 Li1 O1 -2.9(2) . . . .
C6 N1 Li1 O1 173.92(13) . . . .
C4 N1 Li1 O1 -102.5(2) . . . 3_655
C6 N1 Li1 O1 74.4(2) . . . 3_655
C4 N1 Li1 O2 121.72(17) . . . .
C6 N1 Li1 O2 -61.4(2) . . . .
C4 N1 Li1 Li1 -46.0(3) . . . 3_655
C6 N1 Li1 Li1 130.8(2) . . . 3_655
