# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2130636'
loop_
_audit_author_name
_audit_author_address
'Liling Cao'
;Sichuan Normal University
China
;
_audit_update_record             
;
2022-04-30 deposited with the CCDC.	2022-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H4 K Li O5'
_chemical_formula_weight         166.10

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   8.5885(3)
_cell_length_b                   7.5236(2)
_cell_length_c                   9.3685(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     605.36(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.827
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2170
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.473
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.752
_diffrn_reflns_point_group_measured_fraction_full 0.793
_reflns_number_total             1045
_reflns_number_gt                1039
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.470
_reflns_Friedel_fraction_max     0.511
_reflns_Friedel_fraction_full    0.567

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0408P)²+0.1539P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.126(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 328 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.91(4)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         1045
_refine_ls_number_parameters     108
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0240
_refine_ls_wR_factor_ref         0.0655
_refine_ls_wR_factor_gt          0.0655
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
K1 K 0.36313(6) 0.22342(7) 0.64380(8) 0.0246(2) Uani 1 1 d . . . . .
O5 O 0.6293(2) -0.0002(3) 0.6688(2) 0.0314(6) Uani 1 1 d . . . . .
O2 O 0.0870(2) 0.0021(2) 0.6772(2) 0.0259(5) Uani 1 1 d . . . . .
O3 O 0.4470(3) 0.1930(3) 0.9331(3) 0.0299(5) Uani 1 1 d . . . . .
O1 O 0.4219(2) 0.4049(3) 0.4007(3) 0.0279(5) Uani 1 1 d . . . . .
C2 C 0.3696(3) 0.4023(3) 0.2765(3) 0.0179(5) Uani 1 1 d . . . . .
C1 C 0.2420(3) 0.2651(4) 0.2443(4) 0.0224(6) Uani 1 1 d . . . . .
C3 C 0.6976(3) -0.0769(3) 0.7697(3) 0.0210(5) Uani 1 1 d . . . . .
O4 O 0.7172(2) -0.0080(2) 0.8907(3) 0.0284(5) Uani 1 1 d . . . . .
Li1 Li 0.5818(6) 0.5541(6) 0.4743(5) 0.0249(10) Uani 1 1 d . . . . .
H3A H 0.418(5) 0.121(5) 1.003(5) 0.043(11) Uiso 1 1 d . . . . .
H3B H 0.537(6) 0.147(6) 0.913(6) 0.067(14) Uiso 1 1 d . . . . .
H1A H 0.204(4) 0.283(4) 0.156(5) 0.037(9) Uiso 1 1 d . . . . .
H1B H 0.159(5) 0.295(5) 0.303(6) 0.040(11) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
K1 O1 2.703(2) . ?
K1 O3 2.814(3) . ?
K1 O2 2.8388(19) 4 ?
K1 O5 2.848(2) . ?
K1 O5 2.903(2) 4_455 ?
K1 O2 2.914(2) . ?
K1 O4 2.954(2) 2_654 ?
K1 C3 3.238(3) 4_455 ?
K1 C2 3.373(3) 3_545 ?
K1 O4 3.392(2) 4_455 ?
K1 Li1 3.498(5) . ?
K1 Li1 3.551(5) 2_665 ?
O5 C3 1.253(3) . ?
O2 C2 1.253(3) 3_545 ?
O2 Li1 1.948(6) 4_455 ?
O3 Li1 1.958(5) 2_665 ?
O1 C2 1.248(4) . ?
O1 Li1 1.902(5) . ?
C2 C1 1.535(4) . ?
C1 C3 1.527(4) 2_654 ?
C3 O4 1.258(4) . ?
O4 Li1 1.952(5) 3_645 ?

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 K1 O3 143.60(7) . . ?
O1 K1 O2 66.34(6) . 4 ?
O3 K1 O2 77.28(7) . 4 ?
O1 K1 O5 102.58(7) . . ?
O3 K1 O5 70.56(7) . . ?
O2 K1 O5 82.94(6) 4 . ?
O1 K1 O5 80.49(6) . 4_455 ?
O3 K1 O5 99.08(7) . 4_455 ?
O2 K1 O5 86.44(6) 4 4_455 ?
O5 K1 O5 166.55(8) . 4_455 ?
O1 K1 O2 122.08(6) . . ?
O3 K1 O2 93.35(6) . . ?
O2 K1 O2 162.73(7) 4 . ?
O5 K1 O2 107.86(6) . . ?
O5 K1 O2 80.69(6) 4_455 . ?
O1 K1 O4 69.18(6) . 2_654 ?
O3 K1 O4 142.03(6) . 2_654 ?
O2 K1 O4 130.22(6) 4 2_654 ?
O5 K1 O4 85.95(6) . 2_654 ?
O5 K1 O4 107.26(6) 4_455 2_654 ?
O2 K1 O4 65.32(6) . 2_654 ?
O1 K1 C3 88.51(7) . 4_455 ?
O3 K1 C3 80.12(7) . 4_455 ?
O2 K1 C3 70.11(6) 4 4_455 ?
O5 K1 C3 143.87(7) . 4_455 ?
O5 K1 C3 22.72(6) 4_455 4_455 ?
O2 K1 C3 94.18(6) . 4_455 ?
O4 K1 C3 129.82(6) 2_654 4_455 ?
O1 K1 C2 141.55(7) . 3_545 ?
O3 K1 C2 74.83(7) . 3_545 ?
O2 K1 C2 151.86(7) 4 3_545 ?
O5 K1 C2 91.26(6) . 3_545 ?
O5 K1 C2 94.26(6) 4_455 3_545 ?
O2 K1 C2 21.43(6) . 3_545 ?
O4 K1 C2 76.37(6) 2_654 3_545 ?
C3 K1 C2 101.19(6) 4_455 3_545 ?
O1 K1 O4 108.95(6) . 4_455 ?
O3 K1 O4 59.27(6) . 4_455 ?
O2 K1 O4 73.50(5) 4 4_455 ?
O5 K1 O4 127.83(6) . 4_455 ?
O5 K1 O4 40.22(6) 4_455 4_455 ?
O2 K1 O4 89.25(5) . 4_455 ?
O4 K1 O4 143.85(2) 2_654 4_455 ?
C3 K1 O4 21.72(6) 4_455 4_455 ?
C2 K1 O4 88.96(6) 3_545 4_455 ?
O1 K1 Li1 32.63(9) . . ?
O3 K1 Li1 110.97(10) . . ?
O2 K1 Li1 33.82(9) 4 . ?
O5 K1 Li1 91.53(9) . . ?
O5 K1 Li1 84.14(9) 4_455 . ?
O2 K1 Li1 153.09(10) . . ?
O4 K1 Li1 98.69(9) 2_654 . ?
C3 K1 Li1 79.45(10) 4_455 . ?
C2 K1 Li1 174.14(10) 3_545 . ?
O4 K1 Li1 93.39(9) 4_455 . ?
O1 K1 Li1 118.13(9) . 2_665 ?
O3 K1 Li1 33.34(8) . 2_665 ?
O2 K1 Li1 58.05(9) 4 2_665 ?
O5 K1 Li1 95.73(9) . 2_665 ?
O5 K1 Li1 71.55(9) 4_455 2_665 ?
O2 K1 Li1 106.52(9) . 2_665 ?
O4 K1 Li1 171.73(9) 2_654 2_665 ?
C3 K1 Li1 49.74(9) 4_455 2_665 ?
C2 K1 Li1 95.47(9) 3_545 2_665 ?
O4 K1 Li1 32.55(9) 4_455 2_665 ?
Li1 K1 Li1 89.37(5) . 2_665 ?
C3 O5 K1 135.23(18) . . ?
C3 O5 K1 93.83(15) . 4 ?
K1 O5 K1 97.17(6) . 4 ?
C2 O2 Li1 127.0(2) 3_545 4_455 ?
C2 O2 K1 136.02(18) 3_545 4_455 ?
Li1 O2 K1 91.99(16) 4_455 4_455 ?
C2 O2 K1 100.37(15) 3_545 . ?
Li1 O2 K1 92.18(17) 4_455 . ?
K1 O2 K1 97.11(6) 4_455 . ?
Li1 O3 K1 94.47(16) 2_665 . ?
C2 O1 Li1 127.4(3) . . ?
C2 O1 K1 135.25(17) . . ?
Li1 O1 K1 97.33(18) . . ?
O1 C2 O2 125.2(2) . 3_554 ?
O1 C2 C1 116.8(3) . . ?
O2 C2 C1 118.0(3) 3_554 . ?
O1 C2 K1 123.08(18) . 3_554 ?
O2 C2 K1 58.20(14) 3_554 3_554 ?
C1 C2 K1 89.20(15) . 3_554 ?
C3 C1 C2 110.5(2) 2_654 . ?
O5 C3 O4 123.6(2) . . ?
O5 C3 C1 117.9(3) . 2_655 ?
O4 C3 C1 118.5(3) . 2_655 ?
O5 C3 K1 63.45(14) . 4 ?
O4 C3 K1 86.05(16) . 4 ?
C1 C3 K1 123.77(17) 2_655 4 ?
C3 O4 Li1 125.3(2) . 3_645 ?
C3 O4 K1 117.79(17) . 2_655 ?
Li1 O4 K1 90.92(17) 3_645 2_655 ?
C3 O4 K1 72.23(16) . 4 ?
Li1 O4 K1 78.22(16) 3_645 4 ?
K1 O4 K1 168.55(8) 2_655 4 ?
O1 Li1 O2 104.0(2) . 4 ?
O1 Li1 O4 110.6(3) . 3_654 ?
O2 Li1 O4 108.6(3) 4 3_654 ?
O1 Li1 O3 114.3(3) . 2_664 ?
O2 Li1 O3 113.9(2) 4 2_664 ?
O4 Li1 O3 105.4(2) 3_654 2_664 ?
O1 Li1 K1 50.03(13) . . ?
O2 Li1 K1 54.20(13) 4 . ?
O4 Li1 K1 119.1(2) 3_654 . ?
O3 Li1 K1 135.5(2) 2_664 . ?
O1 Li1 K1 93.4(2) . 2_664 ?
O2 Li1 K1 161.8(2) 4 2_664 ?
O4 Li1 K1 69.23(16) 3_654 2_664 ?
O3 Li1 K1 52.19(14) 2_664 2_664 ?
K1 Li1 K1 143.38(16) . 2_664 ?
O1 Li1 K1 107.8(2) . 4 ?
O2 Li1 K1 54.74(14) 4 4 ?
O4 Li1 K1 55.91(14) 3_654 4 ?
O3 Li1 K1 137.9(2) 2_664 4 ?
K1 Li1 K1 75.24(10) . 4 ?
K1 Li1 K1 125.02(14) 2_664 4 ?

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
Li1 O1 C2 O2 -1.2(4) . . . 3_554 ?
K1 O1 C2 O2 179.08(18) . . . 3_554 ?
Li1 O1 C2 C1 178.7(2) . . . . ?
K1 O1 C2 C1 -1.0(4) . . . . ?
Li1 O1 C2 K1 -73.1(3) . . . 3_554 ?
K1 O1 C2 K1 107.2(2) . . . 3_554 ?
O1 C2 C1 C3 -60.5(3) . . . 2_654 ?
O2 C2 C1 C3 119.4(3) 3_554 . . 2_654 ?
K1 C2 C1 C3 172.3(2) 3_554 . . 2_654 ?
K1 O5 C3 O4 -39.3(4) . . . . ?
K1 O5 C3 O4 64.9(3) 4 . . . ?
K1 O5 C3 C1 139.8(2) . . . 2_655 ?
K1 O5 C3 C1 -116.0(2) 4 . . 2_655 ?
K1 O5 C3 K1 -104.2(2) . . . 4 ?
O5 C3 O4 Li1 -115.0(3) . . . 3_645 ?
C1 C3 O4 Li1 66.0(4) 2_655 . . 3_645 ?
K1 C3 O4 Li1 -60.7(2) 4 . . 3_645 ?
O5 C3 O4 K1 131.7(2) . . . 2_655 ?
C1 C3 O4 K1 -47.3(3) 2_655 . . 2_655 ?
K1 C3 O4 K1 -173.97(10) 4 . . 2_655 ?
O5 C3 O4 K1 -54.3(2) . . . 4 ?
C1 C3 O4 K1 126.6(2) 2_655 . . 4 ?

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.043

