# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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 1944070'
loop_
_audit_author_name
_audit_author_address
'Rafal Petrus'
;Wroclaw University of Science and Technology
Poland
;
_audit_update_record             
;
2019-07-30 deposited with the CCDC.	2019-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H42 Li6 O18'
_chemical_formula_sum            'C48 H42 Li6 O18'
_chemical_formula_weight         948.45

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.183(4)
_cell_length_b                   12.029(6)
_cell_length_c                   13.174(8)
_cell_angle_alpha                65.36(2)
_cell_angle_beta                 75.12(2)
_cell_angle_gamma                84.37(2)
_cell_volume                     1139.1(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2884
_cell_measurement_theta_min      2.9085
_cell_measurement_theta_max      36.8160

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'KUMA KM4 CCD κ-geometry diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10125
_diffrn_reflns_av_unetI/netI     0.0871
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.909
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4925
_reflns_number_gt                3231
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND  (Brandenburg, 2007)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0611P)²+0.0938P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4925
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_ref         0.1559
_refine_ls_wR_factor_gt          0.1313
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
Li1 Li 0.6399(6) 0.3847(4) 0.6120(4) 0.0223(10) Uani 1 1 d . . . . .
Li2 Li 0.3893(6) 0.6085(4) 0.5886(4) 0.0232(10) Uani 1 1 d . . . . .
Li3 Li 0.6959(6) 0.6175(4) 0.3744(4) 0.0224(10) Uani 1 1 d . . . . .
O1 O 0.4553(2) 0.45035(15) 0.69190(14) 0.0173(4) Uani 1 1 d . . . . .
O2 O 0.6919(2) 0.25897(16) 0.74259(15) 0.0221(4) Uani 1 1 d . . . . .
O3 O 0.6213(2) 0.12025(16) 0.92295(15) 0.0274(5) Uani 1 1 d . . . . .
C1 C 0.4168(3) 0.4159(2) 0.8049(2) 0.0180(6) Uani 1 1 d . . . . .
C2 C 0.3044(3) 0.4865(2) 0.8547(2) 0.0225(6) Uani 1 1 d . . . . .
H2 H 0.2597 0.5592 0.8058 0.027 Uiso 1 1 calc R U . . .
C3 C 0.2577(4) 0.4536(3) 0.9715(2) 0.0273(7) Uani 1 1 d . . . . .
H3 H 0.1827 0.5039 1.0016 0.033 Uiso 1 1 calc R U . . .
C4 C 0.3195(4) 0.3470(3) 1.0463(2) 0.0284(7) Uani 1 1 d . . . . .
H4 H 0.2869 0.3240 1.1271 0.034 Uiso 1 1 calc R U . . .
C5 C 0.4282(3) 0.2764(2) 1.0011(2) 0.0237(6) Uani 1 1 d . . . . .
H5 H 0.4693 0.2031 1.0518 0.028 Uiso 1 1 calc R U . . .
C6 C 0.4811(3) 0.3085(2) 0.8818(2) 0.0181(6) Uani 1 1 d . . . . .
C7 C 0.6052(3) 0.2311(2) 0.8403(2) 0.0195(6) Uani 1 1 d . . . . .
C8 C 0.7377(4) 0.0389(3) 0.8847(3) 0.0309(7) Uani 1 1 d . . . . .
H8A H 0.6997 0.0248 0.8263 0.046 Uiso 1 1 calc R U . . .
H8B H 0.7411 -0.0393 0.9503 0.046 Uiso 1 1 calc R U . . .
H8C H 0.8509 0.0761 0.8517 0.046 Uiso 1 1 calc R U . . .
O4 O 0.5111(2) 0.70383(14) 0.43595(14) 0.0175(4) Uani 1 1 d . . . . .
O5 O 0.2845(2) 0.74151(15) 0.62032(15) 0.0216(4) Uani 1 1 d . . . . .
O6 O 0.1641(2) 0.92499(16) 0.56452(16) 0.0268(5) Uani 1 1 d . . . . .
C9 C 0.5134(3) 0.8250(2) 0.3870(2) 0.0171(5) Uani 1 1 d . . . . .
C10 C 0.6257(3) 0.8862(2) 0.2791(2) 0.0213(6) Uani 1 1 d . . . . .
H10 H 0.6977 0.8395 0.2430 0.026 Uiso 1 1 calc R U . . .
C11 C 0.6334(3) 1.0126(2) 0.2246(2) 0.0224(6) Uani 1 1 d . . . . .
H11 H 0.7113 1.0507 0.1525 0.027 Uiso 1 1 calc R U . . .
C12 C 0.5294(3) 1.0849(2) 0.2733(2) 0.0232(6) Uani 1 1 d . . . . .
H12 H 0.5363 1.1716 0.2361 0.028 Uiso 1 1 calc R U . . .
C13 C 0.4159(3) 1.0272(2) 0.3773(2) 0.0211(6) Uani 1 1 d . . . . .
H13 H 0.3425 1.0756 0.4106 0.025 Uiso 1 1 calc R U . . .
C14 C 0.4051(3) 0.8993(2) 0.4356(2) 0.0180(6) Uani 1 1 d . . . . .
C15 C 0.2833(3) 0.8459(2) 0.5473(2) 0.0187(6) Uani 1 1 d . . . . .
C16 C 0.0377(4) 0.8779(3) 0.6726(2) 0.0308(7) Uani 1 1 d . . . . .
H16A H -0.0173 0.8055 0.6795 0.046 Uiso 1 1 calc R U . . .
H16B H -0.0471 0.9409 0.6749 0.046 Uiso 1 1 calc R U . . .
H16C H 0.0922 0.8556 0.7365 0.046 Uiso 1 1 calc R U . . .
O7 O 0.7791(2) 0.46377(15) 0.45878(14) 0.0178(4) Uani 1 1 d . . . . .
O8 O 0.8879(2) 0.67185(16) 0.25078(15) 0.0217(4) Uani 1 1 d . . . . .
O9 O 1.1008(2) 0.63011(16) 0.12766(15) 0.0247(5) Uani 1 1 d . . . . .
C17 C 0.9345(3) 0.4258(2) 0.4288(2) 0.0164(5) Uani 1 1 d . . . . .
C18 C 0.9928(3) 0.3161(2) 0.5057(2) 0.0195(6) Uani 1 1 d . . . . .
H18 H 0.9212 0.2732 0.5794 0.023 Uiso 1 1 calc R U . . .
C19 C 1.1493(3) 0.2697(2) 0.4771(2) 0.0204(6) Uani 1 1 d . . . . .
H19 H 1.1835 0.1956 0.5309 0.024 Uiso 1 1 calc R U . . .
C20 C 1.2592(3) 0.3303(2) 0.3698(2) 0.0211(6) Uani 1 1 d . . . . .
H20 H 1.3681 0.2987 0.3504 0.025 Uiso 1 1 calc R U . . .
C21 C 1.2061(3) 0.4364(2) 0.2931(2) 0.0194(6) Uani 1 1 d . . . . .
H21 H 1.2793 0.4773 0.2196 0.023 Uiso 1 1 calc R U . . .
C22 C 1.0461(3) 0.4868(2) 0.3200(2) 0.0162(5) Uani 1 1 d . . . . .
C23 C 1.0014(3) 0.6027(2) 0.2340(2) 0.0193(6) Uani 1 1 d . . . . .
C24 C 1.0563(4) 0.7395(2) 0.0379(2) 0.0281(7) Uani 1 1 d . . . . .
H24A H 0.9406 0.7313 0.0336 0.042 Uiso 1 1 calc R U . . .
H24B H 1.1346 0.7512 -0.0359 0.042 Uiso 1 1 calc R U . . .
H24C H 1.0636 0.8103 0.0553 0.042 Uiso 1 1 calc R U . . .


_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

Li1 O2 1.873(5) . ?
Li1 O1 1.912(5) . ?
Li1 O7 1.926(5) . ?
Li1 O4 2.069(5) 2_666 ?
Li2 O5 1.891(5) . ?
Li2 O4 1.904(5) . ?
Li2 O1 1.944(5) . ?
Li2 O7 2.043(5) 2_666 ?
Li3 O7 1.883(5) . ?
Li3 O8 1.883(5) . ?
Li3 O4 1.946(5) . ?
Li3 O1 2.075(5) 2_666 ?
O1 C1 1.325(3) . ?
O2 C7 1.221(3) . ?
O3 C7 1.345(3) . ?
O3 C8 1.449(3) . ?
C1 C2 1.414(4) . ?
C1 C6 1.422(3) . ?
C2 C3 1.375(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.368(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.408(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.467(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O4 C9 1.325(3) . ?
O4 Li1 2.069(5) 2_666 ?
O5 C15 1.224(3) . ?
O6 C15 1.339(3) . ?
O6 C16 1.451(3) . ?
C9 C10 1.413(3) . ?
C9 C14 1.423(3) . ?
C10 C11 1.385(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.404(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.468(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O7 C17 1.327(3) . ?
O7 Li2 2.043(5) 2_666 ?
O8 C23 1.225(3) . ?
O9 C23 1.348(3) . ?
O9 C24 1.446(3) . ?
C17 C18 1.416(3) . ?
C17 C22 1.418(3) . ?
C18 C19 1.371(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.398(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.371(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.412(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.468(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
O2 Li1 O1 96.7(2) . . ?
O2 Li1 O7 130.0(3) . . ?
O1 Li1 O7 128.7(3) . . ?
O2 Li1 O4 102.6(2) . 2_666 ?
O1 Li1 O4 95.0(2) . 2_666 ?
O7 Li1 O4 94.0(2) . 2_666 ?
O5 Li2 O4 96.3(2) . . ?
O5 Li2 O1 129.9(3) . . ?
O4 Li2 O1 126.3(2) . . ?
O5 Li2 O7 108.0(2) . 2_666 ?
O4 Li2 O7 95.5(2) . 2_666 ?
O1 Li2 O7 94.3(2) . 2_666 ?
O7 Li3 O8 97.6(2) . . ?
O7 Li3 O4 125.7(2) . . ?
O8 Li3 O4 132.5(3) . . ?
O7 Li3 O1 95.1(2) . 2_666 ?
O8 Li3 O1 101.5(2) . 2_666 ?
O4 Li3 O1 93.7(2) . 2_666 ?
C1 O1 Li1 123.5(2) . . ?
C1 O1 Li2 121.9(2) . . ?
Li1 O1 Li2 111.0(2) . . ?
C1 O1 Li3 117.12(19) . 2_666 ?
Li1 O1 Li3 85.5(2) . 2_666 ?
Li2 O1 Li3 83.7(2) . 2_666 ?
C7 O2 Li1 124.2(2) . . ?
C7 O3 C8 115.2(2) . . ?
O1 C1 C2 120.0(2) . . ?
O1 C1 C6 123.4(2) . . ?
C2 C1 C6 116.6(2) . . ?
C3 C2 C1 122.3(3) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C2 C3 C4 120.7(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 118.6(3) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 122.2(3) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C5 C6 C1 119.6(2) . . ?
C5 C6 C7 118.6(2) . . ?
C1 C6 C7 121.8(2) . . ?
O2 C7 O3 120.0(2) . . ?
O2 C7 C6 126.6(2) . . ?
O3 C7 C6 113.4(2) . . ?
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 . . ?
C9 O4 Li2 124.4(2) . . ?
C9 O4 Li3 118.1(2) . . ?
Li2 O4 Li3 114.0(2) . . ?
C9 O4 Li1 116.96(19) . 2_666 ?
Li2 O4 Li1 84.8(2) . 2_666 ?
Li3 O4 Li1 84.8(2) . 2_666 ?
C15 O5 Li2 124.1(2) . . ?
C15 O6 C16 115.8(2) . . ?
O4 C9 C10 119.4(2) . . ?
O4 C9 C14 123.7(2) . . ?
C10 C9 C14 116.9(2) . . ?
C11 C10 C9 121.6(2) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 121.3(3) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C13 C12 C11 118.1(2) . . ?
C13 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
C12 C13 C14 122.3(2) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C13 C14 C9 119.8(2) . . ?
C13 C14 C15 118.5(2) . . ?
C9 C14 C15 121.7(2) . . ?
O5 C15 O6 120.9(2) . . ?
O5 C15 C14 126.3(2) . . ?
O6 C15 C14 112.7(2) . . ?
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 . . ?
C17 O7 Li3 124.0(2) . . ?
C17 O7 Li1 121.4(2) . . ?
Li3 O7 Li1 112.7(2) . . ?
C17 O7 Li2 110.66(19) . 2_666 ?
Li3 O7 Li2 86.2(2) . 2_666 ?
Li1 O7 Li2 85.0(2) . 2_666 ?
C23 O8 Li3 122.3(2) . . ?
C23 O9 C24 115.6(2) . . ?
O7 C17 C18 119.7(2) . . ?
O7 C17 C22 123.3(2) . . ?
C18 C17 C22 116.9(2) . . ?
C19 C18 C17 122.1(2) . . ?
C19 C18 H18 118.9 . . ?
C17 C18 H18 118.9 . . ?
C18 C19 C20 120.8(2) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C21 C20 C19 118.5(2) . . ?
C21 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
C20 C21 C22 122.1(2) . . ?
C20 C21 H21 118.9 . . ?
C22 C21 H21 118.9 . . ?
C21 C22 C17 119.5(2) . . ?
C21 C22 C23 118.5(2) . . ?
C17 C22 C23 121.9(2) . . ?
O8 C23 O9 120.2(2) . . ?
O8 C23 C22 126.8(2) . . ?
O9 C23 C22 113.0(2) . . ?
O9 C24 H24A 109.5 . . ?
O9 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O9 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
O1 Li1 O2 C7 8.5(3) . . . . ?
O7 Li1 O2 C7 165.7(3) . . . . ?
O4 Li1 O2 C7 -88.1(3) 2_666 . . . ?
Li1 O1 C1 C2 165.8(2) . . . . ?
Li2 O1 C1 C2 9.4(4) . . . . ?
Li3 O1 C1 C2 -90.6(3) 2_666 . . . ?
Li1 O1 C1 C6 -15.1(4) . . . . ?
Li2 O1 C1 C6 -171.6(2) . . . . ?
Li3 O1 C1 C6 88.5(3) 2_666 . . . ?
O1 C1 C2 C3 178.7(2) . . . . ?
C6 C1 C2 C3 -0.5(4) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C4 C5 C6 C1 -1.9(4) . . . . ?
C4 C5 C6 C7 176.6(2) . . . . ?
O1 C1 C6 C5 -177.5(2) . . . . ?
C2 C1 C6 C5 1.6(4) . . . . ?
O1 C1 C6 C7 4.1(4) . . . . ?
C2 C1 C6 C7 -176.8(2) . . . . ?
Li1 O2 C7 O3 160.2(2) . . . . ?
Li1 O2 C7 C6 -21.3(4) . . . . ?
C8 O3 C7 O2 -3.7(3) . . . . ?
C8 O3 C7 C6 177.6(2) . . . . ?
C8 O3 C7 Li1 19.3(5) . . . . ?
C5 C6 C7 O2 -162.2(2) . . . . ?
C1 C6 C7 O2 16.3(4) . . . . ?
C5 C6 C7 O3 16.5(3) . . . . ?
C1 C6 C7 O3 -165.1(2) . . . . ?
C5 C6 C7 Li1 -174.0(2) . . . . ?
C1 C6 C7 Li1 4.5(3) . . . . ?
O4 Li2 O5 C15 12.2(3) . . . . ?
O1 Li2 O5 C15 162.4(3) . . . . ?
O7 Li2 O5 C15 -85.6(3) 2_666 . . . ?
Li1 Li2 O5 C15 -36.9(3) 2_666 . . . ?
Li3 Li2 O5 C15 -126.2(3) 2_666 . . . ?
Li1 Li2 O5 C15 123.4(5) . . . . ?
Li3 Li2 O5 C15 24.1(4) . . . . ?
Li2 O4 C9 C10 171.6(2) . . . . ?
Li3 O4 C9 C10 13.7(3) . . . . ?
Li1 O4 C9 C10 -85.4(3) 2_666 . . . ?
Li2 O4 C9 C14 -10.0(4) . . . . ?
Li3 O4 C9 C14 -167.9(2) . . . . ?
Li1 O4 C9 C14 93.1(3) 2_666 . . . ?
O4 C9 C10 C11 -179.8(2) . . . . ?
C14 C9 C10 C11 1.7(4) . . . . ?
C9 C10 C11 C12 -0.7(4) . . . . ?
C10 C11 C12 C13 -0.9(4) . . . . ?
C11 C12 C13 C14 1.4(4) . . . . ?
C12 C13 C14 C9 -0.3(4) . . . . ?
C12 C13 C14 C15 178.5(2) . . . . ?
O4 C9 C14 C13 -179.7(2) . . . . ?
C10 C9 C14 C13 -1.2(4) . . . . ?
O4 C9 C14 C15 1.5(4) . . . . ?
C10 C9 C14 C15 180.0(2) . . . . ?
Li2 O5 C15 O6 156.9(2) . . . . ?
Li2 O5 C15 C14 -23.5(4) . . . . ?
C16 O6 C15 O5 -1.2(3) . . . . ?
C16 O6 C15 C14 179.2(2) . . . . ?
C16 O6 C15 Li2 25.5(5) . . . . ?
C13 C14 C15 O5 -161.6(3) . . . . ?
C9 C14 C15 O5 17.2(4) . . . . ?
C13 C14 C15 O6 17.9(3) . . . . ?
C9 C14 C15 O6 -163.3(2) . . . . ?
C13 C14 C15 Li2 -174.7(2) . . . . ?
C9 C14 C15 Li2 4.1(3) . . . . ?
O8 Li3 O7 C17 3.6(3) . . . . ?
O4 Li3 O7 C17 -155.8(2) . . . . ?
O1 Li3 O7 C17 105.9(2) 2_666 . . . ?
O8 Li3 O7 Li1 168.25(19) . . . . ?
O4 Li3 O7 Li1 8.9(4) . . . . ?
O1 Li3 O7 Li1 -89.4(2) 2_666 . . . ?
Li2 Li3 O7 Li1 -82.9(2) 2_666 . . . ?
Li1 Li3 O7 Li1 -47.1(3) 2_666 . . . ?
C23 Li3 O7 Li1 173.61(18) . . . . ?
Li2 Li3 O7 Li1 3.6(2) . . . . ?
O8 Li3 O7 Li2 -108.8(2) . . . 2_666 ?
O4 Li3 O7 Li2 91.8(3) . . . 2_666 ?
O1 Li3 O7 Li2 -6.49(19) 2_666 . . 2_666 ?
Li1 Li3 O7 Li2 35.8(2) 2_666 . . 2_666 ?
C23 Li3 O7 Li2 -103.48(16) . . . 2_666 ?
Li1 Li3 O7 Li2 82.9(2) . . . 2_666 ?
Li2 Li3 O7 Li2 86.51(19) . . . 2_666 ?
O7 Li3 O8 C23 13.9(3) . . . . ?
O4 Li3 O8 C23 171.0(3) . . . . ?
O1 Li3 O8 C23 -82.9(3) 2_666 . . . ?
Li3 O7 C17 C18 171.3(2) . . . . ?
Li1 O7 C17 C18 7.9(3) . . . . ?
Li2 O7 C17 C18 -89.0(3) 2_666 . . . ?
Li3 O7 C17 C22 -11.5(4) . . . . ?
Li1 O7 C17 C22 -174.9(2) . . . . ?
Li2 O7 C17 C22 88.2(3) 2_666 . . . ?
O7 C17 C18 C19 177.0(2) . . . . ?
C22 C17 C18 C19 -0.3(4) . . . . ?
C17 C18 C19 C20 0.4(4) . . . . ?
C18 C19 C20 C21 -0.8(4) . . . . ?
C19 C20 C21 C22 1.0(4) . . . . ?
C20 C21 C22 C17 -0.9(4) . . . . ?
C20 C21 C22 C23 178.3(2) . . . . ?
O7 C17 C22 C21 -176.7(2) . . . . ?
C18 C17 C22 C21 0.5(3) . . . . ?
O7 C17 C22 C23 4.1(4) . . . . ?
C18 C17 C22 C23 -178.6(2) . . . . ?
Li3 O8 C23 O9 155.3(2) . . . . ?
Li3 O8 C23 C22 -24.7(4) . . . . ?
C24 O9 C23 O8 -3.7(3) . . . . ?
C24 O9 C23 C22 176.4(2) . . . . ?
C24 O9 C23 Li3 25.2(5) . . . . ?
C21 C22 C23 O8 -162.9(2) . . . . ?
C17 C22 C23 O8 16.3(4) . . . . ?
C21 C22 C23 O9 17.1(3) . . . . ?
C17 C22 C23 O9 -163.8(2) . . . . ?
C21 C22 C23 Li3 -177.0(2) . . . . ?
C17 C22 C23 Li3 2.2(3) . . . . ?

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
C10 H10 O8 0.95 2.41 3.271(4) 151.0 .
C18 H18 O2 0.95 2.42 3.297(4) 153.5 .

_refine_diff_density_max         0.284
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.069

_chemical_properties_physical    Air-sensitive,Moisture-sensitive,Hygroscopic
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1944071'
loop_
_audit_author_name
_audit_author_address
'Rafal Petrus'
;Wroclaw University of Science and Technology
Poland
;
_audit_update_record             
;
2019-07-30 deposited with the CCDC.	2019-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H15 Li O6'
_chemical_formula_sum            'C16 H15 Li O6'
_chemical_formula_weight         310.22

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.982(3)
_cell_length_b                   11.477(5)
_cell_length_c                   26.122(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.98(2)
_cell_angle_gamma                90
_cell_volume                     1488.0(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2786
_cell_measurement_theta_min      2.9435
_cell_measurement_theta_max      36.8156

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'KUMA KM4 CCD κ-geometry diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10884
_diffrn_reflns_av_unetI/netI     0.0749
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.944
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3249
_reflns_number_gt                2110
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND  (Brandenburg, 2007)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0525P)²+0.2189P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3249
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1346
_refine_ls_wR_factor_gt          0.1140
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
Li1 Li 0.3199(8) 0.4806(3) 0.38197(16) 0.0268(9) Uani 1 1 d . . . . .
O1 O 0.6236(3) 0.38412(13) 0.37613(6) 0.0250(4) Uani 1 1 d . . . . .
O2 O 0.2680(3) 0.41454(14) 0.44839(6) 0.0267(4) Uani 1 1 d . . . . .
O3 O 0.3065(3) 0.28785(14) 0.51352(6) 0.0296(4) Uani 1 1 d . . . . .
O4 O -0.0026(3) 0.47562(14) 0.33712(6) 0.0260(4) Uani 1 1 d . . . . .
H4A H -0.1310 0.4386 0.3482 0.039 Uiso 1 1 d R U . . .
O5 O 0.3701(3) 0.64226(13) 0.36638(6) 0.0264(4) Uani 1 1 d . . . . .
O6 O 0.2766(3) 0.81910(13) 0.33423(6) 0.0277(4) Uani 1 1 d . . . . .
C1 C 0.6811(4) 0.28280(19) 0.39944(9) 0.0203(5) Uani 1 1 d . . . . .
C2 C 0.8702(5) 0.2071(2) 0.37985(9) 0.0244(5) Uani 1 1 d . . . . .
H2 H 0.9563 0.2295 0.3503 0.029 Uiso 1 1 calc R U . . .
C3 C 0.9323(5) 0.1014(2) 0.40264(10) 0.0266(6) Uani 1 1 d . . . . .
H3 H 1.0610 0.0521 0.3888 0.032 Uiso 1 1 calc R U . . .
C4 C 0.8087(5) 0.0660(2) 0.44577(9) 0.0263(6) Uani 1 1 d . . . . .
H4 H 0.8502 -0.0076 0.4611 0.032 Uiso 1 1 calc R U . . .
C5 C 0.6257(5) 0.1387(2) 0.46601(9) 0.0241(5) Uani 1 1 d . . . . .
H5 H 0.5428 0.1147 0.4957 0.029 Uiso 1 1 calc R U . . .
C6 C 0.5584(4) 0.24746(19) 0.44387(9) 0.0197(5) Uani 1 1 d . . . . .
C7 C 0.3660(5) 0.3252(2) 0.46709(9) 0.0216(5) Uani 1 1 d . . . . .
C8 C 0.1213(5) 0.3601(2) 0.53921(10) 0.0338(6) Uani 1 1 d . . . . .
H8A H 0.1957 0.4389 0.5436 0.051 Uiso 1 1 calc R U . . .
H8B H 0.0949 0.3268 0.5729 0.051 Uiso 1 1 calc R U . . .
H8C H -0.0521 0.3637 0.5184 0.051 Uiso 1 1 calc R U . . .
C9 C -0.0999(5) 0.55352(19) 0.30204(9) 0.0213(5) Uani 1 1 d . . . . .
C10 C -0.3198(5) 0.5240(2) 0.26709(9) 0.0252(6) Uani 1 1 d . . . . .
H10 H -0.3962 0.4484 0.2684 0.030 Uiso 1 1 calc R U . . .
C11 C -0.4262(5) 0.6020(2) 0.23124(9) 0.0240(5) Uani 1 1 d . . . . .
H11 H -0.5757 0.5800 0.2082 0.029 Uiso 1 1 calc R U . . .
C12 C -0.3179(5) 0.7130(2) 0.22817(9) 0.0254(6) Uani 1 1 d . . . . .
H12 H -0.3921 0.7669 0.2032 0.030 Uiso 1 1 calc R U . . .
C13 C -0.1017(5) 0.7440(2) 0.26177(9) 0.0238(5) Uani 1 1 d . . . . .
H13 H -0.0261 0.8196 0.2594 0.029 Uiso 1 1 calc R U . . .
C14 C 0.0101(4) 0.66677(19) 0.29956(8) 0.0181(5) Uani 1 1 d . . . . .
C15 C 0.2341(5) 0.7040(2) 0.33606(9) 0.0213(5) Uani 1 1 d . . . . .
C16 C 0.4947(5) 0.8623(2) 0.36856(10) 0.0301(6) Uani 1 1 d . . . . .
H16A H 0.4682 0.8384 0.4038 0.045 Uiso 1 1 calc R U . . .
H16B H 0.4995 0.9476 0.3666 0.045 Uiso 1 1 calc R U . . .
H16C H 0.6653 0.8305 0.3587 0.045 Uiso 1 1 calc R U . . .


_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
Li1 O1 1.892(4) . ?
Li1 O4 1.906(5) . ?
Li1 O5 1.921(4) . ?
Li1 O2 1.931(4) . ?
O1 C1 1.332(3) . ?
O2 C7 1.220(3) . ?
O3 C7 1.344(3) . ?
O3 C8 1.448(3) . ?
O4 C9 1.340(3) . ?
O4 H4A 0.8403 . ?
O5 C15 1.223(3) . ?
O6 C15 1.339(3) . ?
O6 C16 1.436(3) . ?
C1 C2 1.410(3) . ?
C1 C6 1.417(3) . ?
C2 C3 1.374(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.404(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.478(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.405(3) . ?
C9 C14 1.414(3) . ?
C10 C11 1.369(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.376(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.405(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.467(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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 124.8(2) . . ?
O1 Li1 O5 115.4(2) . . ?
O4 Li1 O5 90.97(18) . . ?
O1 Li1 O2 90.75(18) . . ?
O4 Li1 O2 111.7(2) . . ?
O5 Li1 O2 126.9(2) . . ?
C1 O1 Li1 128.0(2) . . ?
C7 O2 Li1 127.6(2) . . ?
C7 O3 C8 115.79(19) . . ?
C9 O4 Li1 129.47(19) . . ?
C9 O4 H4A 109.5 . . ?
Li1 O4 H4A 115.4 . . ?
C15 O5 Li1 128.5(2) . . ?
C15 O6 C16 115.59(18) . . ?
O1 C1 C2 119.7(2) . . ?
O1 C1 C6 122.2(2) . . ?
C2 C1 C6 118.0(2) . . ?
C3 C2 C1 121.3(2) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 120.7(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.3(2) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.6(2) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 119.2(2) . . ?
C5 C6 C7 120.5(2) . . ?
C1 C6 C7 120.3(2) . . ?
O2 C7 O3 121.2(2) . . ?
O2 C7 C6 126.5(2) . . ?
O3 C7 C6 112.3(2) . . ?
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 119.9(2) . . ?
O4 C9 C14 121.7(2) . . ?
C10 C9 C14 118.3(2) . . ?
C11 C10 C9 121.4(2) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 120.7(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 119.1(2) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 121.7(2) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C13 C14 C9 118.7(2) . . ?
C13 C14 C15 120.4(2) . . ?
C9 C14 C15 120.9(2) . . ?
O5 C15 O6 120.9(2) . . ?
O5 C15 C14 126.8(2) . . ?
O6 C15 C14 112.19(19) . . ?
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_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(3) . . . . ?
O5 Li1 O1 C1 155.8(2) . . . . ?
O2 Li1 O1 C1 23.8(3) . . . . ?
Li1 O1 C1 C2 161.5(2) . . . . ?
Li1 O1 C1 C6 -18.6(3) . . . . ?
O1 C1 C2 C3 -179.4(2) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C4 C5 C6 C7 -178.5(2) . . . . ?
O1 C1 C6 C5 179.1(2) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
O1 C1 C6 C7 -2.0(3) . . . . ?
C2 C1 C6 C7 177.9(2) . . . . ?
Li1 O2 C7 O3 -178.3(2) . . . . ?
Li1 O2 C7 C6 2.5(4) . . . . ?
C8 O3 C7 O2 -0.1(3) . . . . ?
C8 O3 C7 C6 179.3(2) . . . . ?
C5 C6 C7 O2 -170.7(2) . . . . ?
C1 C6 C7 O2 10.4(4) . . . . ?
C5 C6 C7 O3 10.0(3) . . . . ?
C1 C6 C7 O3 -168.89(19) . . . . ?
Li1 O4 C9 C10 169.5(2) . . . . ?
Li1 O4 C9 C14 -11.6(4) . . . . ?
O4 C9 C10 C11 179.1(2) . . . . ?
C14 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C12 C13 C14 C9 1.5(3) . . . . ?
C12 C13 C14 C15 -177.7(2) . . . . ?
O4 C9 C14 C13 180.0(2) . . . . ?
C10 C9 C14 C13 -1.1(3) . . . . ?
O4 C9 C14 C15 -0.9(3) . . . . ?
C10 C9 C14 C15 178.0(2) . . . . ?
Li1 O5 C15 O6 171.7(2) . . . . ?
Li1 O5 C15 C14 -6.7(4) . . . . ?
C16 O6 C15 O5 2.0(3) . . . . ?
C16 O6 C15 C14 -179.43(19) . . . . ?
C13 C14 C15 O5 -170.4(2) . . . . ?
C9 C14 C15 O5 10.4(3) . . . . ?
C13 C14 C15 O6 11.1(3) . . . . ?
C9 C14 C15 O6 -168.1(2) . . . . ?

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 1.60 2.437(2) 170.9 1_455

_refine_diff_density_max         0.280
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.059

_chemical_properties_physical    Air-sensitive,Moisture-sensitive,Hygroscopic
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1944072'
loop_
_audit_author_name
_audit_author_address
'Rafal Petrus'
;Wroclaw University of Science and Technology
Poland
;
_audit_update_record             
;
2019-07-30 deposited with the CCDC.	2019-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H15 Li O5'
_chemical_formula_sum            'C10 H15 Li O5'
_chemical_formula_weight         222.16

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'
O O 0.0492 0.0322 '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'

_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'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   16.678(4)
_cell_length_b                   10.147(3)
_cell_length_c                   7.008(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1186.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2473
_cell_measurement_theta_min      4.3730
_cell_measurement_theta_max      73.7460

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.920
_exptl_crystal_size_mid          0.460
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    0.821
_shelx_estimated_absorpt_T_min   0.519
_shelx_estimated_absorpt_T_max   0.762
_exptl_absorpt_correction_T_min  0.620
_exptl_absorpt_correction_T_max  0.811
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_reflns_number            2830
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_av_R_equivalents  0.0106
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         5.102
_diffrn_reflns_theta_max         69.918
_diffrn_reflns_theta_full        68.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.671
_diffrn_reflns_point_group_measured_fraction_full 0.675
_reflns_number_total             1508
_reflns_number_gt                1495
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.250
_reflns_Friedel_fraction_max     0.294
_reflns_Friedel_fraction_full    0.297

_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       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND  (Brandenburg, 2007)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0622P)²+0.1837P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 294 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.37(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1508
_refine_ls_number_parameters     148
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0861
_refine_ls_wR_factor_gt          0.0858
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.091
_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
Li1 Li 0.55848(16) 0.4001(3) 0.5069(5) 0.0174(6) Uani 1 1 d . . . . .
O1 O 0.44609(6) 0.38225(11) 0.4903(2) 0.0153(3) Uani 1 1 d . . . . .
O2 O 0.57911(7) 0.22536(12) 0.4171(2) 0.0187(3) Uani 1 1 d . . . . .
O3 O 0.55416(7) 0.03388(12) 0.2737(2) 0.0203(3) Uani 1 1 d . . . . .
C1 C 0.40583(9) 0.27860(17) 0.4300(3) 0.0135(4) Uani 1 1 d . . . . .
C2 C 0.32060(10) 0.28180(17) 0.4311(3) 0.0167(4) Uani 1 1 d . . . . .
H2 H 0.2944 0.3576 0.4805 0.020 Uiso 1 1 calc R U . . .
C3 C 0.27469(10) 0.17941(19) 0.3633(3) 0.0194(4) Uani 1 1 d . . . . .
H3 H 0.2179 0.1855 0.3661 0.023 Uiso 1 1 calc R U . . .
C4 C 0.31164(11) 0.06617(19) 0.2899(3) 0.0209(4) Uani 1 1 d . . . . .
H4 H 0.2801 -0.0046 0.2423 0.025 Uiso 1 1 calc R U . . .
C5 C 0.39393(11) 0.05849(18) 0.2876(3) 0.0187(4) Uani 1 1 d . . . . .
H5 H 0.4188 -0.0183 0.2375 0.022 Uiso 1 1 calc R U . . .
C6 C 0.44229(10) 0.16165(18) 0.3576(3) 0.0152(4) Uani 1 1 d . . . . .
C7 C 0.53019(10) 0.14676(16) 0.3545(3) 0.0144(4) Uani 1 1 d . . . . .
C8 C 0.63986(10) 0.01356(18) 0.2662(3) 0.0207(4) Uani 1 1 d . . . . .
H8A H 0.6612 0.0087 0.3963 0.031 Uiso 1 1 calc R U . . .
H8B H 0.6651 0.0871 0.1984 0.031 Uiso 1 1 calc R U . . .
H8C H 0.6514 -0.0690 0.1990 0.031 Uiso 1 1 calc R U . . .
O4 O 0.60064(8) 0.41974(13) 0.7618(3) 0.0216(3) Uani 1 1 d . . . . .
H4A H 0.5853 0.4802 0.8351 0.032 Uiso 1 1 d R U . . .
C9 C 0.6353(2) 0.3190(2) 0.8704(5) 0.0493(8) Uani 1 1 d . . . . .
H9A H 0.6633 0.2574 0.7858 0.074 Uiso 1 1 calc R U . . .
H9B H 0.5933 0.2720 0.9405 0.074 Uiso 1 1 calc R U . . .
H9C H 0.6736 0.3571 0.9611 0.074 Uiso 1 1 calc R U . . .
O5 O 0.60317(7) 0.53703(13) 0.3434(2) 0.0199(3) Uani 1 1 d . . . . .
H5A H 0.5836 0.5579 0.2372 0.030 Uiso 1 1 d R U . . .
C10 C 0.63361(15) 0.6546(2) 0.4269(4) 0.0338(5) Uani 1 1 d . . . . .
H10A H 0.6569 0.6343 0.5519 0.051 Uiso 1 1 calc R U . . .
H10B H 0.5899 0.7183 0.4424 0.051 Uiso 1 1 calc R U . . .
H10C H 0.6750 0.6921 0.3438 0.051 Uiso 1 1 calc R U . . .


_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
Li1 O1 1.887(3) . ?
Li1 O2 1.913(3) . ?
Li1 O4 1.930(4) . ?
Li1 O5 1.949(4) . ?
O1 C1 1.317(2) . ?
O2 C7 1.222(2) . ?
O3 C7 1.339(2) . ?
O3 C8 1.4451(19) . ?
C1 C2 1.422(2) . ?
C1 C6 1.427(3) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.402(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.410(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.474(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O4 C9 1.399(3) . ?
O4 H4A 0.8400 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
O5 C10 1.422(3) . ?
O5 H5A 0.8400 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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 O2 93.97(14) . . ?
O1 Li1 O4 115.41(19) . . ?
O2 Li1 O4 109.54(17) . . ?
O1 Li1 O5 114.34(17) . . ?
O2 Li1 O5 113.49(18) . . ?
O4 Li1 O5 109.35(15) . . ?
C1 O1 Li1 127.08(14) . . ?
C7 O2 Li1 127.08(14) . . ?
C7 O3 C8 115.63(13) . . ?
O1 C1 C2 119.31(15) . . ?
O1 C1 C6 124.11(14) . . ?
C2 C1 C6 116.56(15) . . ?
C3 C2 C1 122.52(16) . . ?
C3 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
C2 C3 C4 120.07(15) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 119.34(17) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.67(17) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 119.83(15) . . ?
C5 C6 C7 119.20(16) . . ?
C1 C6 C7 120.96(15) . . ?
O2 C7 O3 120.72(15) . . ?
O2 C7 C6 126.28(16) . . ?
O3 C7 C6 113.00(14) . . ?
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 . . ?
C9 O4 Li1 125.37(17) . . ?
C9 O4 H4A 109.0 . . ?
Li1 O4 H4A 122.0 . . ?
O4 C9 H9A 109.5 . . ?
O4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 O5 Li1 119.52(18) . . ?
C10 O5 H5A 106.9 . . ?
Li1 O5 H5A 123.5 . . ?
O5 C10 H10A 109.5 . . ?
O5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
O2 Li1 O1 C1 -1.3(3) . . . . ?
O4 Li1 O1 C1 -115.2(2) . . . . ?
O5 Li1 O1 C1 116.7(2) . . . . ?
Li1 O1 C1 C2 178.7(2) . . . . ?
Li1 O1 C1 C6 -2.9(3) . . . . ?
O1 C1 C2 C3 177.37(18) . . . . ?
C6 C1 C2 C3 -1.2(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C1 -1.2(3) . . . . ?
C4 C5 C6 C7 178.9(2) . . . . ?
O1 C1 C6 C5 -176.84(19) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
O1 C1 C6 C7 3.1(3) . . . . ?
C2 C1 C6 C7 -178.47(18) . . . . ?
Li1 O2 C7 O3 171.3(2) . . . . ?
Li1 O2 C7 C6 -8.9(3) . . . . ?
C8 O3 C7 O2 -0.2(3) . . . . ?
C8 O3 C7 C6 179.97(17) . . . . ?
C5 C6 C7 O2 -176.9(2) . . . . ?
C1 C6 C7 O2 3.2(3) . . . . ?
C5 C6 C7 O3 2.9(3) . . . . ?
C1 C6 C7 O3 -176.97(17) . . . . ?

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 1.85 2.685(2) 177.7 2_665
O5 H5A O1 0.84 1.90 2.733(2) 171.6 2_664

_refine_diff_density_max         0.233
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.036


#=====================  End of CIF submission =================================
_chemical_properties_physical    Air-sensitive,Moisture-sensitive,Hygroscopic
