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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/7/71/55/7715550.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_7715550
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 H15 Li O6'
_chemical_formula_sum            'C16 H15 Li O6'
_chemical_formula_weight         310.22
_chemical_properties_physical    Moisture-sensitive,Hygroscopic
_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     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                90
_cell_angle_beta                 94.95(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9781(10)
_cell_length_b                   11.479(2)
_cell_length_c                   26.144(5)
_cell_measurement_reflns_used    16317
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      60
_cell_measurement_theta_min      3.3
_cell_volume                     1488.4(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.42a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.42a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.42a (Rigaku OD, 2022)'
_computing_molecular_graphics    'DIAMOND  (Brandenburg, 2007)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            34153
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         69.987
_diffrn_reflns_theta_min         3.394
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.881
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.801
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.42a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0467
_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)+(0.0768P)²+0.4874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1292
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2351
_reflns_number_total             2804
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt00648h2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7715548--7715558.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7715550
_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   0.810
_shelx_estimated_absorpt_t_max   0.991
_oxdiff_exptl_absorpt_empirical_full_min 0.647
_oxdiff_exptl_absorpt_empirical_full_max 1.463
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
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
Li1 Li 0.3179(6) 0.4798(3) 0.38164(12) 0.0369(7) Uani 1 1 d . . . . .
O1 O 0.6220(2) 0.38390(11) 0.37604(5) 0.0333(3) Uani 1 1 d . . . . .
O2 O 0.2676(3) 0.41441(11) 0.44854(5) 0.0357(3) Uani 1 1 d . . . . .
O3 O 0.3065(3) 0.28788(12) 0.51342(5) 0.0388(3) Uani 1 1 d . . . . .
O4 O -0.0041(2) 0.47554(11) 0.33742(5) 0.0358(3) Uani 1 1 d . . . . .
H4A H -0.1324 0.4360 0.3471 0.054 Uiso 1 1 calc R U . . .
O5 O 0.3696(2) 0.64206(11) 0.36641(5) 0.0348(3) Uani 1 1 d . . . . .
O6 O 0.2760(3) 0.81896(11) 0.33434(5) 0.0359(3) Uani 1 1 d . . . . .
C1 C 0.6801(3) 0.28316(15) 0.39929(7) 0.0295(4) Uani 1 1 d . . . . .
C2 C 0.8694(3) 0.20731(16) 0.37983(7) 0.0334(4) Uani 1 1 d . . . . .
H2 H 0.9558 0.2299 0.3504 0.040 Uiso 1 1 calc R U . . .
C3 C 0.9318(4) 0.10168(16) 0.40236(8) 0.0366(4) Uani 1 1 d . . . . .
H3 H 1.0598 0.0523 0.3883 0.044 Uiso 1 1 calc R U . . .
C4 C 0.8086(4) 0.06617(16) 0.44583(7) 0.0372(4) Uani 1 1 d . . . . .
H4 H 0.8503 -0.0074 0.4612 0.045 Uiso 1 1 calc R U . . .
C5 C 0.6262(4) 0.13919(16) 0.46608(7) 0.0349(4) Uani 1 1 d . . . . .
H5 H 0.5440 0.1156 0.4959 0.042 Uiso 1 1 calc R U . . .
C6 C 0.5581(3) 0.24787(15) 0.44383(6) 0.0295(4) Uani 1 1 d . . . . .
C7 C 0.3654(3) 0.32534(16) 0.46703(6) 0.0303(4) Uani 1 1 d . . . . .
C8 C 0.1212(4) 0.3606(2) 0.53929(7) 0.0439(5) Uani 1 1 d . . . . .
H8A H 0.1976 0.4389 0.5442 0.066 Uiso 1 1 calc R U . . .
H8B H 0.0925 0.3265 0.5727 0.066 Uiso 1 1 calc R U . . .
H8C H -0.0514 0.3655 0.5183 0.066 Uiso 1 1 calc R U . . .
C9 C -0.0995(3) 0.55312(16) 0.30219(7) 0.0307(4) Uani 1 1 d . . . . .
C10 C -0.3200(4) 0.52339(16) 0.26734(7) 0.0338(4) Uani 1 1 d . . . . .
H10 H -0.3968 0.4478 0.2687 0.041 Uiso 1 1 calc R U . . .
C11 C -0.4265(4) 0.60195(17) 0.23123(7) 0.0345(4) Uani 1 1 d . . . . .
H11 H -0.5758 0.5799 0.2082 0.041 Uiso 1 1 calc R U . . .
C12 C -0.3180(4) 0.71303(16) 0.22815(7) 0.0349(4) Uani 1 1 d . . . . .
H12 H -0.3918 0.7668 0.2031 0.042 Uiso 1 1 calc R U . . .
C13 C -0.1016(4) 0.74425(16) 0.26191(7) 0.0330(4) Uani 1 1 d . . . . .
H13 H -0.0263 0.8200 0.2598 0.040 Uiso 1 1 calc R U . . .
C14 C 0.0095(3) 0.66595(15) 0.29946(6) 0.0296(4) Uani 1 1 d . . . . .
C15 C 0.2344(3) 0.70384(15) 0.33613(6) 0.0296(4) Uani 1 1 d . . . . .
C16 C 0.4949(4) 0.86304(17) 0.36867(8) 0.0402(5) Uani 1 1 d . . . . .
H16A H 0.4694 0.8390 0.4039 0.060 Uiso 1 1 calc R U . . .
H16B H 0.4981 0.9483 0.3668 0.060 Uiso 1 1 calc R U . . .
H16C H 0.6660 0.8318 0.3587 0.060 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 0.0181 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 O4 125.42(19) . . ?
O1 Li1 O5 115.17(17) . . ?
O4 Li1 O5 91.15(14) . . ?
O1 Li1 O2 90.63(14) . . ?
O4 Li1 O2 111.84(17) . . ?
O5 Li1 O2 126.20(18) . . ?
C1 O1 Li1 128.13(15) . . ?
C7 O2 Li1 127.32(15) . . ?
C7 O3 C8 115.65(14) . . ?
C9 O4 Li1 129.34(15) . . ?
C9 O4 H4A 109.5 . . ?
Li1 O4 H4A 117.1 . . ?
C15 O5 Li1 128.28(15) . . ?
C15 O6 C16 115.81(14) . . ?
O1 C1 C2 119.94(16) . . ?
O1 C1 C6 122.22(16) . . ?
C2 C1 C6 117.84(16) . . ?
C3 C2 C1 121.64(17) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 120.51(17) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.08(17) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.69(18) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 119.23(16) . . ?
C5 C6 C7 120.44(16) . . ?
C1 C6 C7 120.33(16) . . ?
O2 C7 O3 121.19(16) . . ?
O2 C7 C6 126.57(16) . . ?
O3 C7 C6 112.23(15) . . ?
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 . . ?
O4 C9 C10 119.66(16) . . ?
O4 C9 C14 122.11(15) . . ?
C10 C9 C14 118.21(16) . . ?
C11 C10 C9 121.17(17) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 120.77(17) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 119.15(16) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 121.21(17) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C9 C14 C13 119.49(16) . . ?
C9 C14 C15 120.81(15) . . ?
C13 C14 C15 119.69(16) . . ?
O5 C15 O6 121.16(16) . . ?
O5 C15 C14 126.52(16) . . ?
O6 C15 C14 112.29(15) . . ?
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 . . ?
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 1.888(3) . ?
Li1 O4 1.894(3) . ?
Li1 O5 1.927(3) . ?
Li1 O2 1.939(3) . ?
O1 C1 1.327(2) . ?
O2 C7 1.215(2) . ?
O3 C7 1.343(2) . ?
O3 C8 1.454(2) . ?
O4 C9 1.338(2) . ?
O4 H4A 0.8400 . ?
O5 C15 1.221(2) . ?
O6 C15 1.339(2) . ?
O6 C16 1.442(2) . ?
C1 C2 1.410(2) . ?
C1 C6 1.418(2) . ?
C2 C3 1.372(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.398(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.406(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.476(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.407(2) . ?
C9 C14 1.409(3) . ?
C10 C11 1.378(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.409(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.475(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
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
O4 H4A O1 0.84 1.61 2.4319(17) 166.3 1_455
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
_geom_torsion_publ_flag
O4 Li1 O1 C1 -93.5(2) . . . . ?
O5 Li1 O1 C1 155.33(16) . . . . ?
O2 Li1 O1 C1 24.2(2) . . . . ?
O1 Li1 O4 C9 -109.1(2) . . . . ?
O5 Li1 O4 C9 13.3(2) . . . . ?
O2 Li1 O4 C9 143.44(16) . . . . ?
Li1 O1 C1 C2 161.23(17) . . . . ?
Li1 O1 C1 C6 -18.9(3) . . . . ?
O1 C1 C2 C3 -179.03(16) . . . . ?
C6 C1 C2 C3 1.1(3) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C4 C5 C6 C7 -178.84(16) . . . . ?
O1 C1 C6 C5 179.08(15) . . . . ?
C2 C1 C6 C5 -1.0(2) . . . . ?
O1 C1 C6 C7 -2.0(2) . . . . ?
C2 C1 C6 C7 177.92(15) . . . . ?
Li1 O2 C7 O3 -177.82(17) . . . . ?
Li1 O2 C7 C6 3.2(3) . . . . ?
C8 O3 C7 O2 -0.1(2) . . . . ?
C8 O3 C7 C6 178.98(15) . . . . ?
C5 C6 C7 O2 -171.05(17) . . . . ?
C1 C6 C7 O2 10.0(3) . . . . ?
C5 C6 C7 O3 9.9(2) . . . . ?
C1 C6 C7 O3 -169.02(15) . . . . ?
Li1 O4 C9 C10 169.01(18) . . . . ?
Li1 O4 C9 C14 -12.6(3) . . . . ?
O4 C9 C10 C11 178.74(16) . . . . ?
C14 C9 C10 C11 0.3(3) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
O4 C9 C14 C13 -179.22(16) . . . . ?
C10 C9 C14 C13 -0.9(2) . . . . ?
O4 C9 C14 C15 -0.6(3) . . . . ?
C10 C9 C14 C15 177.77(15) . . . . ?
C12 C13 C14 C9 0.9(3) . . . . ?
C12 C13 C14 C15 -177.75(16) . . . . ?
Li1 O5 C15 O6 171.61(17) . . . . ?
Li1 O5 C15 C14 -6.5(3) . . . . ?
C16 O6 C15 O5 2.4(2) . . . . ?
C16 O6 C15 C14 -179.28(14) . . . . ?
C9 C14 C15 O5 10.6(3) . . . . ?
C13 C14 C15 O5 -170.82(17) . . . . ?
C9 C14 C15 O6 -167.68(15) . . . . ?
C13 C14 C15 O6 10.9(2) . . . . ?
