Chemical lithiation reveals the structures of conjugated tetralithium dicarboxylates.
Griffiths, Kieran; Cook, Chris; Seymour, Valerie R.; Bragg, Ryan J.; Halcovitch, Nathan R.; Griffin, John M.; Chemical communications (Cambridge, England) 61 (2025) 11991–11994; doi:10.1039/d5cc03043a

data_7134792
_publ_section_title
;
 Chemical lithiation reveals the structures of conjugated tetralithium
 dicarboxylates.
;
_journal_issue                   64
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11991
_journal_page_last               11994
_journal_paper_doi               10.1039/d5cc03043a
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C6 H3 Li O2'
_chemical_formula_sum            'C6 H3 Li O2'
_chemical_formula_weight         114.02
_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     dual
_audit_creation_date             2025-05-13
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-05-13 deposited with the CCDC.	2025-06-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.7210(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2674(2)
_cell_length_b                   5.33790(10)
_cell_length_c                   8.62550(10)
_cell_measurement_reflns_used    5399
_cell_measurement_temperature    291.5(3)
_cell_measurement_theta_max      75.7930
_cell_measurement_theta_min      4.3210
_cell_volume                     467.267(14)
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.5(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2282
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -66.00  33.00   1.00    1.00    --  -41.43  37.00  90.00   99
  2  \w   -116.00 -17.00   1.00    1.00    --  -41.43 -37.00  90.00   99
  3  \w    -66.00  33.00   1.00    1.00    --  -41.43  37.00   0.00   99
  4  \w    103.00 178.00   1.00    1.41    --  112.00  77.00  30.00   75
  5  \w     39.00 109.00   1.00    1.41    --  112.00-111.00  60.00   70
  6  \w     39.00 138.00   1.00    1.41    --  112.00 -45.00-120.00   99
  7  \w     59.00 178.00   1.00    1.41    --  112.00  15.00 -90.00  119
  8  \w     39.00 109.00   1.00    1.41    --  112.00-111.00   0.00   70
  9  \w     39.00 109.00   1.00    1.41    --  112.00-111.00 120.00   70
 10  \w    104.00 178.00   1.00    1.41    --  112.00 111.00 120.00   74
 11  \w     36.00 145.00   1.00    1.41    --  112.00 -77.00 120.00  109
 12  \w    -86.00  -6.00   1.00    1.00    --  -41.43 125.00 150.00   80
 13  \w   -114.00 -13.00   1.00    1.00    --  -41.43 -57.00-120.00  101
 14  \w   -116.00 -17.00   1.00    1.00    --  -41.43 -37.00 -30.00   99
 15  \w     83.00 178.00   1.00    1.41    --  112.00  61.00 -60.00   95
 16  \w     84.00 178.00   1.00    1.41    --  112.00  30.00 120.00   94
 17  \w     83.00 178.00   1.00    1.41    --  112.00  61.00-180.00   95
 18  \w     83.00 178.00   1.00    1.41    --  112.00  61.00-120.00   95
 19  \w     86.00 178.00   1.00    1.41    --  112.00  45.00  60.00   92
 20  \w     84.00 178.00   1.00    1.41    --  112.00  30.00   7.00   94
 21  \w   -114.00 -13.00   1.00    1.00    --  -41.43 -57.00 -60.00  101
 22  \w   -114.00 -13.00   1.00    1.00    --  -41.43 -57.00-180.00  101
 23  \w   -114.00 -13.00   1.00    1.00    --  -41.43 -57.00  60.00  101
 24  \w     83.00 178.00   1.00    1.41    --  112.00  61.00 -90.00   95
 25  \w     86.00 178.00   1.00    1.41    --  112.00  45.00 150.00   92
 26  \w     86.00 178.00   1.00    1.41    --  112.00  45.00  30.00   92
 27  \w     83.00 178.00   1.00    1.41    --  112.00  61.00-150.00   95
 28  \w     39.00 109.00   1.00    1.41    --  112.00-111.00-150.00   70
 29  \w     29.00 107.00   1.00    1.41    --  112.00 -94.00-120.00   78
 30  \w   -114.00 -13.00   1.00    1.00    --  -41.43 -57.00  90.00  101
 31  \w   -114.00 -13.00   1.00    1.00    --  -41.43 -57.00   0.00  101
 32  \w     27.00  95.00   1.00    1.00    --   41.43-125.00 -60.00   68
 33  \w     83.00 108.00   1.00    1.41    --  112.00  61.00 120.00   25
 34  \w     83.00 178.00   1.00    1.41    --  112.00  61.00  60.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1445709000
_diffrn_orient_matrix_UB_12      0.0265898000
_diffrn_orient_matrix_UB_13      0.0258482000
_diffrn_orient_matrix_UB_21      -0.0460364000
_diffrn_orient_matrix_UB_22      -0.1078755000
_diffrn_orient_matrix_UB_23      -0.1648019000
_diffrn_orient_matrix_UB_31      0.0043612000
_diffrn_orient_matrix_UB_32      -0.2664510000
_diffrn_orient_matrix_UB_33      0.0693367000
_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  0.0272
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7966
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.461
_diffrn_reflns_theta_min         4.357
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.989
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_description       block
_exptl_crystal_F_000             232
_exptl_crystal_preparation       oil
_exptl_crystal_recrystallization_method 'water / acetone vapour diffusion'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         978
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0311
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0483P)^2^+0.1469P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0867
_reflns_Friedel_coverage         0.000
_reflns_number_gt                936
_reflns_number_total             978
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03043a2.cif
_cod_data_source_block           jg201_auto
_cod_depositor_comments
'Adding full bibliography for 7134789--7134792.cif.'
_cod_database_code               7134792
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O Li'
_chemical_oxdiff_usercomment     LiNDC
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C5(H5)
;
_shelx_res_checksum              23014
_shelx_hkl_checksum              92426
_olex2_exptl_crystal_mounting_method 'mitegen loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.517
_oxdiff_exptl_absorpt_empirical_full_min 0.538