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#$Date: 2024-05-05 05:43:56 +0300 (Sun, 05 May 2024) $
#$Revision: 291617 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/55/7715554.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_7715554
loop_
_publ_author_name
'Petrus, Rafał'
'Kowaliński, Adrian'
'Lis, Tadeusz'
_publ_section_title
;
 Recycling primary lithium batteries using a coordination chemistry
 approach: recovery of lithium and manganese residues in the form of
 industrially important materials.
;
_journal_issue                   17
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7450
_journal_page_last               7469
_journal_paper_doi               10.1039/d4dt00648h
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C16 H18 Li2 O8'
_chemical_formula_sum            'C16 H18 Li2 O8'
_chemical_formula_weight         352.18
_chemical_properties_physical    Hygroscopic,Heat-sensitive
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-08-11 deposited with the CCDC.	2024-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                99.32(2)
_cell_angle_beta                 91.04(2)
_cell_angle_gamma                90.12(2)
_cell_formula_units_Z            2
_cell_length_a                   6.442(3)
_cell_length_b                   10.346(2)
_cell_length_c                   12.498(2)
_cell_measurement_reflns_used    1645
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.6437
_cell_measurement_theta_min      3.5815
_cell_volume                     821.8(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'DIAMOND  (Brandenburg, 2007)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.1956
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_unetI/netI     0.0776
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5688
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.976
_diffrn_reflns_theta_min         3.584
_exptl_absorpt_coefficient_mu    0.948
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.781
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b (release 03-02-2012 CrysAlis171 .NET)
(compiled Feb  3 2012,10:37:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.987
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.154
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2994
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.1235
_refine_ls_R_factor_gt           0.1079
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2720
_refine_ls_wR_factor_ref         0.3029
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2195
_reflns_number_total             2994
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt00648h2.cif
_cod_data_source_block           4_t
_cod_depositor_comments
'Adding full bibliography for 7715548--7715558.cif.'
_cod_database_code               7715554
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.727
_shelx_estimated_absorpt_t_max   0.963
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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_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
Li1 Li 0.3137(10) 0.4647(6) 0.5193(5) 0.0305(13) Uani 1 1 d . . . . .
O1 O 0.5721(4) 0.4258(2) 0.58027(19) 0.0271(6) Uani 1 1 d . . . . .
C1 C 0.6237(5) 0.4487(3) 0.6834(3) 0.0241(8) Uani 1 1 d . . . . .
C2 C 0.8119(6) 0.3958(3) 0.7201(3) 0.0272(8) Uani 1 1 d . . . . .
H2 H 0.8965 0.3441 0.6684 0.033 Uiso 1 1 calc R U . . .
C3 C 0.8741(6) 0.4165(3) 0.8256(3) 0.0297(8) Uani 1 1 d . . . . .
H3 H 1.0003 0.3790 0.8460 0.036 Uiso 1 1 calc R U . . .
C4 C 0.7560(6) 0.4924(4) 0.9053(3) 0.0307(8) Uani 1 1 d . . . . .
H4 H 0.8009 0.5066 0.9791 0.037 Uiso 1 1 calc R U . . .
C5 C 0.5726(6) 0.5460(3) 0.8740(3) 0.0282(8) Uani 1 1 d . . . . .
H5 H 0.4909 0.5974 0.9273 0.034 Uiso 1 1 calc R U . . .
C6 C 0.5040(6) 0.5260(3) 0.7646(3) 0.0262(8) Uani 1 1 d . . . . .
C7 C 0.3071(6) 0.5869(3) 0.7370(3) 0.0260(8) Uani 1 1 d . . . . .
O2 O 0.2250(4) 0.5784(2) 0.64697(19) 0.0285(6) Uani 1 1 d . . . . .
O3 O 0.2213(4) 0.6602(2) 0.8231(2) 0.0301(6) Uani 1 1 d . . . . .
C8 C 0.0374(6) 0.7318(4) 0.8013(3) 0.0336(9) Uani 1 1 d . . . . .
H8A H -0.0090 0.7848 0.8688 0.050 Uiso 1 1 calc R U . . .
H8B H -0.0727 0.6700 0.7718 0.050 Uiso 1 1 calc R U . . .
H8C H 0.0691 0.7892 0.7486 0.050 Uiso 1 1 calc R U . . .
O1W O 0.1332(4) 0.3185(2) 0.4701(2) 0.0336(7) Uani 1 1 d . . . . .
H1W H 0.0363 0.3080 0.4235 0.050 Uiso 1 1 d R U . . .
H2W H 0.1146 0.2469 0.4921 0.050 Uiso 1 1 d R U . . .
Li2 Li 0.8149(10) 0.0416(6) 0.5195(5) 0.0298(13) Uani 1 1 d . . . . .
O4 O 1.0730(4) 0.1037(2) 0.58227(19) 0.0270(6) Uani 1 1 d . . . . .
C9 C 1.1219(6) 0.1227(3) 0.6858(3) 0.0266(8) Uani 1 1 d . . . . .
C10 C 1.3085(6) 0.1905(3) 0.7232(3) 0.0274(8) Uani 1 1 d . . . . .
H10 H 1.3952 0.2207 0.6717 0.033 Uiso 1 1 calc R U . . .
C11 C 1.3684(6) 0.2140(3) 0.8301(3) 0.0320(8) Uani 1 1 d . . . . .
H11 H 1.4947 0.2594 0.8509 0.038 Uiso 1 1 calc R U . . .
C12 C 1.2454(6) 0.1719(3) 0.9091(3) 0.0304(8) Uani 1 1 d . . . . .
H12 H 1.2863 0.1891 0.9834 0.036 Uiso 1 1 calc R U . . .
C13 C 1.0642(6) 0.1050(3) 0.8770(3) 0.0314(8) Uani 1 1 d . . . . .
H13 H 0.9811 0.0749 0.9301 0.038 Uiso 1 1 calc R U . . .
C14 C 0.9987(5) 0.0800(3) 0.7673(3) 0.0264(8) Uani 1 1 d . . . . .
C15 C 0.8031(5) 0.0066(3) 0.7380(3) 0.0251(7) Uani 1 1 d . . . . .
O5 O 0.7233(4) -0.0211(2) 0.64729(19) 0.0293(6) Uani 1 1 d . . . . .
O6 O 0.7133(4) -0.0319(3) 0.8238(2) 0.0335(7) Uani 1 1 d . . . . .
C16 C 0.5283(6) -0.1107(4) 0.8018(3) 0.0348(9) Uani 1 1 d . . . . .
H16A H 0.4729 -0.1298 0.8701 0.052 Uiso 1 1 calc R U . . .
H16B H 0.5618 -0.1930 0.7547 0.052 Uiso 1 1 calc R U . . .
H16C H 0.4243 -0.0630 0.7655 0.052 Uiso 1 1 calc R U . . .
O2W O 0.6338(4) 0.1692(2) 0.4710(2) 0.0327(7) Uani 1 1 d . . . . .
H3W H 0.5249 0.1424 0.4365 0.049 Uiso 1 1 d R U . . .
H4W H 0.6106 0.2467 0.5003 0.049 Uiso 1 1 d 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 0.0181 0.0091 '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 0.0008 0.0003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_publ_flag
O1 Li1 O1W 116.4(3) . . ?
O1 Li1 O2 94.7(3) . . ?
O1W Li1 O2 115.0(3) . . ?
O1 Li1 O1 95.8(3) . 2_666 ?
O1W Li1 O1 122.2(3) . 2_666 ?
O2 Li1 O1 107.9(3) . 2_666 ?
C1 O1 Li1 125.9(3) . . ?
C1 O1 Li1 120.1(3) . 2_666 ?
Li1 O1 Li1 84.2(3) . 2_666 ?
O1 C1 C6 124.1(3) . . ?
O1 C1 C2 119.8(3) . . ?
C6 C1 C2 116.1(3) . . ?
C3 C2 C1 122.5(3) . . ?
C3 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
C2 C3 C4 121.3(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 118.4(3) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 120.2(3) . . ?
C5 C6 C7 118.5(3) . . ?
C1 C6 C7 121.3(3) . . ?
O2 C7 O3 120.5(3) . . ?
O2 C7 C6 126.8(3) . . ?
O3 C7 C6 112.7(3) . . ?
C7 O2 Li1 125.2(3) . . ?
C7 O3 C8 116.0(3) . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
Li1 O1W H1W 131.7 . . ?
Li1 O1W H2W 132.3 . . ?
H1W O1W H2W 95.7 . . ?
O4 Li2 O5 94.2(3) . . ?
O4 Li2 O2W 116.7(3) . . ?
O5 Li2 O2W 114.1(3) . . ?
O4 Li2 O4 96.3(3) . 2_756 ?
O5 Li2 O4 109.7(3) . 2_756 ?
O2W Li2 O4 121.3(3) . 2_756 ?
C9 O4 Li2 126.1(3) . . ?
C9 O4 Li2 122.3(3) . 2_756 ?
Li2 O4 Li2 83.7(3) . 2_756 ?
O4 C9 C10 119.9(3) . . ?
O4 C9 C14 124.4(3) . . ?
C10 C9 C14 115.7(3) . . ?
C11 C10 C9 122.9(3) . . ?
C11 C10 H10 118.6 . . ?
C9 C10 H10 118.6 . . ?
C10 C11 C12 120.7(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 118.8(3) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C14 121.6(3) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C9 120.3(3) . . ?
C13 C14 C15 119.0(3) . . ?
C9 C14 C15 120.7(3) . . ?
O5 C15 O6 120.3(3) . . ?
O5 C15 C14 127.1(3) . . ?
O6 C15 C14 112.6(3) . . ?
C15 O5 Li2 125.4(3) . . ?
C15 O6 C16 116.4(3) . . ?
O6 C16 H16A 109.5 . . ?
O6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Li2 O2W H3W 118.2 . . ?
Li2 O2W H4W 129.1 . . ?
H3W O2W H4W 106.3 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Li1 O1 1.889(7) . ?
Li1 O1W 1.919(7) . ?
Li1 O2 1.920(7) . ?
Li1 O1 1.965(6) 2_666 ?
O1 C1 1.309(4) . ?
O1 Li1 1.965(6) 2_666 ?
C1 C6 1.425(5) . ?
C1 C2 1.429(5) . ?
C2 C3 1.355(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.401(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.412(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.478(5) . ?
C7 O2 1.225(4) . ?
C7 O3 1.341(4) . ?
O3 C8 1.444(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O1W H1W 0.8400 . ?
O1W H2W 0.8400 . ?
Li2 O4 1.891(7) . ?
Li2 O5 1.921(7) . ?
Li2 O2W 1.926(6) . ?
Li2 O4 1.954(7) 2_756 ?
Li2 Li2 2.565(13) 2_756 ?
O4 C9 1.309(4) . ?
O4 Li2 1.954(7) 2_756 ?
C9 C10 1.424(5) . ?
C9 C14 1.427(5) . ?
C10 C11 1.366(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.400(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.375(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.410(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.479(5) . ?
C15 O5 1.226(4) . ?
C15 O6 1.344(4) . ?
O6 C16 1.439(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O2W H3W 0.8400 . ?
O2W H4W 0.8400 . ?
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
O1W H1W O2 0.84 2.30 2.999(4) 141.2 2_566
O1W H2W O4 0.84 2.02 2.842(3) 165.5 1_455
O2W H3W O5 0.84 2.18 2.992(4) 164.3 2_656
O2W H4W O1 0.84 1.98 2.814(4) 174.8 .
