#------------------------------------------------------------------------------
#$Date: 2019-11-25 16:14:01 +0200 (Mon, 25 Nov 2019) $
#$Revision: 241292 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/09/4130967.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_4130967
loop_
_publ_author_name
'Guang, Jie'
'Liu, Qiyong'
'Hopson, Russell'
'Kagan, Gerald'
'Li, Weibin'
'Monroe, Thomas B.'
'Williard, Paul G.'
_publ_section_title
;
 Conformational Polymorphism of Lithium Pinacolone Enolate.
;
_journal_issue                   46
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15177
_journal_page_last               15188
_journal_paper_doi               10.1021/jacs.6b08177
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C18 H33 Li3 O3'
_chemical_formula_sum            'C18 H33 Li3 O3'
_chemical_formula_weight         318.28
_chemical_name_systematic        'Pinacolone enolate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-10
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                102.936(3)
_cell_angle_beta                 115.200(3)
_cell_angle_gamma                99.243(3)
_cell_formula_units_Z            2
_cell_length_a                   10.3259(14)
_cell_length_b                   10.7672(14)
_cell_length_c                   10.8895(15)
_cell_measurement_reflns_used    9008
_cell_measurement_temperature    198(2)
_cell_measurement_theta_max      20.76
_cell_measurement_theta_min      2.19
_cell_volume                     1021.7(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      198.21
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.9976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13239
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         20.76
_diffrn_reflns_theta_min         2.03
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_correction_T_min  0.6663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1274 before and 0.0617 after correction.
The Ratio of minimum to maximum transmission is 0.8950.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.0345
_exptl_crystal_description       block
_exptl_crystal_F_000             348.1556
_exptl_crystal_recrystallization_method 'crystallization at -20 C'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.3780
_refine_diff_density_min         -0.2104
_refine_diff_density_rms         0.0421
_refine_ls_d_res_high            1.0025
_refine_ls_d_res_low             10.0423
_refine_ls_goodness_of_fit_ref   1.0574
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    45
_refine_ls_number_parameters     225
_refine_ls_number_reflns         2121
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0574
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0546
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0537P)²+0.9454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1341
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              10
_reflns_limit_l_min              0
_reflns_number_gt                1830
_reflns_number_total             2121
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ja6b08177_si_002.cif
_cod_data_source_block           jg14may13_0m_a
_cod_database_code               4130967
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a X=CH2 refined with fixed occupancy and ADP/Uiso:
 C1(H1a,H1b), C7(H7a,H7b), C13(H13a,H13b)
2.b Idealised Me refined as rotating group:
 C4(H4a,H4b,H4c), C5(H5a,H5b,H5c), C6(H6a,H6b,H6c), C10(H10a,H10b,H10c),
 C11(H11a,H11b,H11c), C12(H12a,H12b,H12c), C16(H16a,H16b,H16c), C17(H17a,H17b,
 H17c), C18(H18a,H18b,H18c)
;
_olex2_submission_original_sample_id jg14may13
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
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_refinement_flags_posn
C1 C 0.2162(4) 0.4361(3) 0.6652(4) 0.0562(9) Uani 1.000000 .
H1a H 0.1492(4) 0.4119(3) 0.7003(4) 0.0674(11) Uiso 1.000000 .
H1b H 0.3017(4) 0.5116(3) 0.7223(4) 0.0674(11) Uiso 1.000000 .
C2 C 0.1902(3) 0.3645(3) 0.5364(3) 0.0398(8) Uani 1.000000 .
C3 C 0.0565(3) 0.2425(3) 0.4384(3) 0.0444(8) Uani 1.000000 .
C4 C -0.0421(3) 0.2652(3) 0.2987(3) 0.0595(10) Uani 1.000000 .
H4a H -0.073(2) 0.3451(12) 0.3208(4) 0.0892(14) Uiso 1.000000 GR
H4b H 0.0143(8) 0.277(2) 0.2470(11) 0.0892(14) Uiso 1.000000 GR
H4c H -0.1309(12) 0.1880(10) 0.2387(11) 0.0892(14) Uiso 1.000000 GR
C5 C 0.1135(4) 0.1241(3) 0.4019(4) 0.0679(11) Uani 1.000000 .
H5a H 0.172(2) 0.1437(10) 0.354(2) 0.1018(16) Uiso 1.000000 GR
H5b H 0.177(2) 0.1080(15) 0.4904(5) 0.1018(16) Uiso 1.000000 GR
H5c H 0.0283(4) 0.0446(6) 0.338(2) 0.1018(16) Uiso 1.000000 GR
C6 C -0.0401(4) 0.2072(4) 0.5066(4) 0.0735(11) Uani 1.000000 .
H6a H 0.0210(8) 0.192(2) 0.5963(14) 0.1103(17) Uiso 1.000000 GR
H6b H -0.081(2) 0.2807(11) 0.527(2) 0.1103(17) Uiso 1.000000 GR
H6c H -0.1224(16) 0.1263(14) 0.4404(12) 0.1103(17) Uiso 1.000000 GR
C7 C 0.4675(3) 0.8250(3) 0.7433(4) 0.0526(9) Uani 1.000000 .
H7a H 0.4566(3) 0.8884(3) 0.8117(4) 0.0631(11) Uiso 1.000000 .
H7b H 0.4058(3) 0.8078(3) 0.6435(4) 0.0631(11) Uiso 1.000000 .
C8 C 0.5692(3) 0.7603(3) 0.7872(3) 0.0388(7) Uani 1.000000 .
C9 C 0.6730(3) 0.7805(3) 0.9433(3) 0.0506(9) Uani 1.000000 .
C10 C 0.6494(4) 0.8851(4) 1.0460(4) 0.0710(11) Uani 1.000000 .
H10a H 0.669(3) 0.9707(7) 1.0304(18) 0.1065(17) Uiso 1.000000 GR
H10b H 0.5461(9) 0.8573(12) 1.0282(18) 0.1065(17) Uiso 1.000000 GR
H10c H 0.7182(19) 0.8942(18) 1.1454(4) 0.1065(17) Uiso 1.000000 GR
C11 C 0.6485(6) 0.6500(4) 0.9726(4) 0.0964(15) Uani 1.000000 .
H11a H 0.5452(11) 0.6195(16) 0.954(3) 0.145(2) Uiso 1.000000 GR
H11b H 0.667(3) 0.5831(10) 0.910(2) 0.145(2) Uiso 1.000000 GR
H11c H 0.718(2) 0.6629(8) 1.0730(10) 0.145(2) Uiso 1.000000 GR
C12 C 0.8344(4) 0.8316(5) 0.9737(4) 0.0988(16) Uani 1.000000 .
H12a H 0.8569(12) 0.7639(13) 0.915(3) 0.148(2) Uiso 1.000000 GR
H12b H 0.8467(10) 0.9135(18) 0.949(3) 0.148(2) Uiso 1.000000 GR
H12c H 0.9028(4) 0.850(3) 1.0758(8) 0.148(2) Uiso 1.000000 GR
C13 C 0.1213(3) 0.5684(3) 0.2162(3) 0.0501(9) Uani 1.000000 .
H13a H 0.0503(3) 0.5833(3) 0.1344(3) 0.0601(10) Uiso 1.000000 .
H13b H 0.0913(3) 0.4997(3) 0.2486(3) 0.0601(10) Uiso 1.000000 .
C14 C 0.2632(3) 0.6437(3) 0.2855(3) 0.0338(7) Uani 1.000000 .
C15 C 0.3190(3) 0.7554(3) 0.2394(3) 0.0402(8) Uani 1.000000 .
C16 C 0.2837(5) 0.8782(4) 0.3032(5) 0.0920(14) Uani 1.000000 .
H16a H 0.333(3) 0.9017(18) 0.4080(5) 0.138(2) Uiso 1.000000 GR
H16b H 0.320(3) 0.9527(9) 0.277(3) 0.138(2) Uiso 1.000000 GR
H16c H 0.1753(6) 0.8591(10) 0.265(2) 0.138(2) Uiso 1.000000 GR
C17 C 0.2424(5) 0.7226(4) 0.0780(4) 0.0923(14) Uani 1.000000 .
H17a H 0.282(2) 0.7969(13) 0.0537(4) 0.138(2) Uiso 1.000000 GR
H17b H 0.261(3) 0.6420(18) 0.0344(5) 0.138(2) Uiso 1.000000 GR
H17c H 0.1346(6) 0.708(3) 0.0413(5) 0.138(2) Uiso 1.000000 GR
C18 C 0.4868(4) 0.7914(4) 0.2969(5) 0.0853(14) Uani 1.000000 .
H18a H 0.5375(4) 0.826(3) 0.4021(5) 0.128(2) Uiso 1.000000 GR
H18b H 0.5145(5) 0.7119(8) 0.266(3) 0.128(2) Uiso 1.000000 GR
H18c H 0.5170(6) 0.859(2) 0.260(3) 0.128(2) Uiso 1.000000 GR
Li1 Li 0.3678(5) 0.5868(5) 0.5690(5) 0.0444(12) Uani 1.000000 .
Li2 Li 0.2891(5) 0.4322(5) 0.3191(5) 0.0430(12) Uani 1.000000 .
Li3 Li 0.5717(5) 0.6889(5) 0.5148(5) 0.0476(13) Uani 1.000000 .
O1 O 0.2829(2) 0.39681(18) 0.48313(19) 0.0414(6) Uani 1.000000 .
O2 O 0.5850(2) 0.66999(19) 0.69200(19) 0.0442(6) Uani 1.000000 .
O3 O 0.3641(2) 0.62668(18) 0.40293(19) 0.0403(5) Uani 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Li -0.00003 0.00005 1.12820 0.75080 0.61750 0.46530 3.95460 1.05240 85.39050
168.26100 0.0377000011504
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
H1b C1 H1a 120.0 . .
C2 C1 H1a 120.0 . .
C2 C1 H1b 120.0 . .
C3 C2 C1 123.4(3) . .
O1 C2 C1 121.4(3) . .
O1 C2 C3 115.2(3) . .
C4 C3 C2 110.3(2) . .
C5 C3 C2 108.5(2) . .
C5 C3 C4 108.5(3) . .
C6 C3 C2 112.9(3) . .
C6 C3 C4 108.1(3) . .
C6 C3 C5 108.5(3) . .
H4a C4 C3 109.5 . .
H4b C4 C3 109.5 . .
H4b C4 H4a 109.5 . .
H4c C4 C3 109.5 . .
H4c C4 H4a 109.5 . .
H4c C4 H4b 109.5 . .
H5a C5 C3 109.5 . .
H5b C5 C3 109.5 . .
H5b C5 H5a 109.5 . .
H5c C5 C3 109.5 . .
H5c C5 H5a 109.5 . .
H5c C5 H5b 109.5 . .
H6a C6 C3 109.5 . .
H6b C6 C3 109.5 . .
H6b C6 H6a 109.5 . .
H6c C6 C3 109.5 . .
H6c C6 H6a 109.5 . .
H6c C6 H6b 109.5 . .
H7b C7 H7a 120.0 . .
C8 C7 H7a 120.0 . .
C8 C7 H7b 120.0 . .
C9 C8 C7 124.2(3) . .
O2 C8 C7 120.7(3) . .
O2 C8 C9 115.1(2) . .
C10 C9 C8 112.4(3) . .
C11 C9 C8 109.7(3) . .
C11 C9 C10 108.9(3) . .
C12 C9 C8 108.4(3) . .
C12 C9 C10 106.8(3) . .
C12 C9 C11 110.6(3) . .
H10a C10 C9 109.5 . .
H10b C10 C9 109.5 . .
H10b C10 H10a 109.5 . .
H10c C10 C9 109.5 . .
H10c C10 H10a 109.5 . .
H10c C10 H10b 109.5 . .
H11a C11 C9 109.5 . .
H11b C11 C9 109.5 . .
H11b C11 H11a 109.5 . .
H11c C11 C9 109.5 . .
H11c C11 H11a 109.5 . .
H11c C11 H11b 109.5 . .
H12a C12 C9 109.5 . .
H12b C12 C9 109.5 . .
H12b C12 H12a 109.5 . .
H12c C12 C9 109.5 . .
H12c C12 H12a 109.5 . .
H12c C12 H12b 109.5 . .
H13b C13 H13a 120.0 . .
C14 C13 H13a 120.0 . .
C14 C13 H13b 120.0 . .
C15 C14 C13 122.8(2) . .
O3 C14 C13 120.9(2) . .
O3 C14 C15 116.3(2) . .
C16 C15 C14 107.3(2) . .
C17 C15 C14 112.5(3) . .
C17 C15 C16 108.1(3) . .
C18 C15 C14 112.2(2) . .
C18 C15 C16 107.4(3) . .
C18 C15 C17 109.1(3) . .
H16a C16 C15 109.5 . .
H16b C16 C15 109.5 . .
H16b C16 H16a 109.5 . .
H16c C16 C15 109.5 . .
H16c C16 H16a 109.5 . .
H16c C16 H16b 109.5 . .
H17a C17 C15 109.5 . .
H17b C17 C15 109.5 . .
H17b C17 H17a 109.5 . .
H17c C17 C15 109.5 . .
H17c C17 H17a 109.5 . .
H17c C17 H17b 109.5 . .
H18a C18 C15 109.5 . .
H18b C18 C15 109.5 . .
H18b C18 H18a 109.5 . .
H18c C18 C15 109.5 . .
H18c C18 H18a 109.5 . .
H18c C18 H18b 109.5 . .
O2 Li1 O1 121.7(3) . .
O3 Li1 O1 98.3(2) . .
O3 Li1 O2 94.4(2) . .
O1 Li2 Li3 47.21(16) . 2_666
O2 Li2 Li3 49.14(16) 2_666 2_666
O2 Li2 O1 96.0(2) 2_666 .
O3 Li2 Li3 113.9(2) . 2_666
O3 Li2 O1 97.1(2) . .
O3 Li2 O2 121.3(3) . 2_666
O1 Li3 Li2 48.98(16) 2_666 2_666
O2 Li3 Li2 46.56(16) . 2_666
O2 Li3 O1 95.2(2) . 2_666
O3 Li3 Li2 120.3(2) . 2_666
O3 Li3 O1 129.6(3) . 2_666
O3 Li3 O2 97.9(2) . .
Li1 O1 C2 105.0(2) . .
Li2 O1 C2 143.5(2) . .
Li2 O1 Li1 82.7(2) . .
Li3 O1 C2 123.4(2) 2_666 .
Li3 O1 Li1 111.7(2) 2_666 .
Li3 O1 Li2 83.8(2) 2_666 .
Li1 O2 C8 93.7(2) . .
Li2 O2 C8 141.3(2) 2_666 .
Li2 O2 Li1 117.8(2) 2_666 .
Li3 O2 C8 124.1(2) . .
Li3 O2 Li1 82.2(2) . .
Li3 O2 Li2 84.3(2) . 2_666
Li1 O3 C14 136.6(2) . .
Li2 O3 C14 92.8(2) . .
Li2 O3 Li1 81.7(2) . .
Li3 O3 C14 135.2(2) . .
Li3 O3 Li1 85.0(2) . .
Li3 O3 Li2 113.0(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 H1a 0.9500 .
C1 H1b 0.9500 .
C1 C2 1.328(4) .
C2 C3 1.519(4) .
C2 O1 1.353(3) .
C3 C4 1.528(4) .
C3 C5 1.532(4) .
C3 C6 1.525(4) .
C4 H4a 0.9800 .
C4 H4b 0.9800 .
C4 H4c 0.9800 .
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 H7a 0.9500 .
C7 H7b 0.9500 .
C7 C8 1.332(4) .
C8 C9 1.515(4) .
C8 O2 1.338(3) .
C9 C10 1.528(4) .
C9 C11 1.515(5) .
C9 C12 1.531(5) .
C10 H10a 0.9800 .
C10 H10b 0.9800 .
C10 H10c 0.9800 .
C11 H11a 0.9800 .
C11 H11b 0.9800 .
C11 H11c 0.9800 .
C12 H12a 0.9800 .
C12 H12b 0.9800 .
C12 H12c 0.9800 .
C13 H13a 0.9500 .
C13 H13b 0.9500 .
C13 C14 1.333(4) .
C14 C15 1.524(4) .
C14 O3 1.336(3) .
C15 C16 1.525(5) .
C15 C17 1.513(5) .
C15 C18 1.515(4) .
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 H18a 0.9800 .
C18 H18b 0.9800 .
C18 H18c 0.9800 .
Li1 O1 1.923(5) .
Li1 O2 1.971(5) .
Li1 O3 1.936(5) .
Li2 Li3 2.546(7) 2_666
Li2 O1 1.932(5) .
Li2 O2 1.857(5) 2_666
Li2 O3 1.960(5) .
Li3 O1 1.879(5) 2_666
Li3 O2 1.935(5) .
Li3 O3 1.865(5) .
