#------------------------------------------------------------------------------ #$Date: 2024-05-28 01:12:14 +0300 (Tue, 28 May 2024) $ #$Revision: 292054 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/17/1571722.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_1571722 loop_ _publ_author_name 'Li, Yang' 'Ok, Kang Min' _publ_section_title ; Crystal clear: unveiling giant birefringence in organic-inorganic cocrystals ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC02569E _journal_year 2024 _chemical_formula_moiety 'C10 H14 Li2 N4 O10, 2(C5 H5 N O)' _chemical_formula_sum 'C20 H24 Li2 N6 O12' _chemical_formula_weight 554.33 _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 dual _audit_creation_date 2024-04-08 _audit_creation_method ; Olex2 1.5 (compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928) ; _audit_update_record ; 2024-04-08 deposited with the CCDC. 2024-05-27 downloaded from the CCDC. ; _cell_angle_alpha 82.101(2) _cell_angle_beta 68.227(2) _cell_angle_gamma 70.184(2) _cell_formula_units_Z 1 _cell_length_a 8.2120(6) _cell_length_b 8.9624(6) _cell_length_c 9.9320(7) _cell_measurement_reflns_used 8708 _cell_measurement_temperature 140 _cell_measurement_theta_max 28.33 _cell_measurement_theta_min 2.81 _cell_volume 638.59(8) _computing_cell_refinement 'SAINT V8.40B (?, 2016)' _computing_data_reduction 'SAINT V8.40B (?, 2016)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 140 _diffrn_detector 'Bruker APEX2 area detector' _diffrn_detector_area_resol_mean 7.9 _diffrn_detector_type 'CCD area detector' _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART APEX2 area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_monochromator 'mirror optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0502 _diffrn_reflns_av_unetI/netI 0.0377 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 14595 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.317 _diffrn_reflns_theta_min 2.416 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_type 'Incoatec I\ms' _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.5588 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1055 before and 0.0893 after correction. The Ratio of minimum to maximum transmission is 0.7494. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.441 _exptl_crystal_description block _exptl_crystal_F_000 288 _exptl_crystal_size_max 0.289 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.178 _refine_diff_density_max 0.434 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.050 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 184 _refine_ls_number_reflns 3158 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.025 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0404 _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/[\s^2^(Fo^2^)+(0.0634P)^2^+0.1873P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1088 _refine_ls_wR_factor_ref 0.1127 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2802 _reflns_number_total 3158 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc02569e2.cif _cod_data_source_block 2 _cod_database_code 1571722 _shelx_shelxl_version_number 2019/1 _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. ; _shelx_estimated_absorpt_t_max 0.979 _shelx_estimated_absorpt_t_min 0.967 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups At 1.5 times of: All O(H,H) groups 2. Restrained distances Li1-H6A \\sim Li1-H6B with sigma of 0.02 3.a Free rotating group: O6(H6A,H6B) 3.b Aromatic/amide H refined with riding coordinates: N4(H4), N2(H2A), C6(H6), C5(H5), C3(H3), C11(H11), C9(H9), C8(H8), C7(H7), C2(H2) ; _shelx_res_file ; TITL 2_a.res in P-1 2.res created by SHELXL-2019/1 at 09:08:36 on 08-Apr-2024 REM Old TITL 2 in P-1 REM SHELXT solution in P-1: R1 0.143, Rweak 0.008, Alpha 0.051 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C10 Li N3 O6 CELL 0.71073 8.212 8.9624 9.932 82.101 68.227 70.184 ZERR 1 0.0006 0.0006 0.0007 0.002 0.002 0.002 LATT 1 SFAC C H Li N O UNIT 20 24 2 6 12 EQIV $1 2-X,-Y,-Z EQIV $2 -1+X,1+Y,+Z EQIV $3 1-X,-Y,1-Z SADI Li1 H6a Li1 H6b L.S. 50 PLAN 5 SIZE 0.178 0.21 0.289 TEMP -133.15 CONF HTAB O6 O2 HTAB O6 O2_$1 HTAB N4 O2_$2 HTAB N2 O5_$3 HTAB N2 O7_$3 BOND list 4 MORE -1 BOND $H fmap 2 acta OMIT -1 -1 1 OMIT 0 -1 1 OMIT 0 0 1 OMIT 0 2 1 OMIT 0 2 2 OMIT 1 -1 1 OMIT 1 1 3 OMIT 1 2 1 OMIT 1 2 2 OMIT 2 -1 1 OMIT 2 2 2 OMIT 2 3 5 REM REM REM WGHT 0.063400 0.187300 FVAR 1.97835 O5 5 0.801968 0.352589 0.350943 11.00000 0.02123 0.03210 = 0.03478 0.00469 -0.01304 -0.00562 AFIX 6 O6 5 1.008620 0.169301 0.072981 11.00000 0.03500 0.02023 = 0.02259 0.00118 -0.00571 -0.01465 H6A 2 0.953665 0.104479 0.129638 11.00000 -1.50000 H6B 2 1.026425 0.144261 -0.014062 11.00000 -1.50000 AFIX 0 O2 5 0.898179 -0.083735 0.215255 11.00000 0.01446 0.02296 = 0.02369 0.00154 -0.00304 -0.00872 O1 5 0.816104 0.549924 0.039030 11.00000 0.01195 0.01967 = 0.02252 0.00364 -0.00382 -0.00350 O7 5 0.956688 0.215281 0.486169 11.00000 0.02412 0.04495 = 0.02330 0.01367 -0.00769 -0.01143 O3 5 1.088530 0.333916 0.289840 11.00000 0.02582 0.03947 = 0.02583 0.00478 -0.00268 -0.02081 N3 4 0.949387 0.300767 0.377101 11.00000 0.01818 0.02071 = 0.01849 0.00021 -0.00349 -0.00648 N4 4 0.255720 0.728443 0.173526 11.00000 0.01189 0.02645 = 0.02456 -0.00191 -0.00512 -0.00630 AFIX 43 H4 2 0.134562 0.768255 0.204093 11.00000 -1.20000 AFIX 0 N2 4 0.396006 -0.148352 0.418453 11.00000 0.01544 0.03301 = 0.02264 -0.00655 -0.00066 -0.01233 AFIX 43 H2A 2 0.287740 -0.163708 0.459631 11.00000 -1.20000 AFIX 0 C6 1 0.571789 0.020039 0.292026 11.00000 0.01885 0.01756 = 0.02126 -0.00048 -0.00717 -0.00387 AFIX 43 H6 2 0.575823 0.121529 0.251099 11.00000 -1.20000 AFIX 0 C5 1 0.548245 0.757703 0.033733 11.00000 0.01626 0.01729 = 0.02186 0.00284 -0.00573 -0.00637 AFIX 43 H5 2 0.618132 0.820162 -0.031178 11.00000 -1.20000 AFIX 0 C3 1 0.336103 0.581699 0.217973 11.00000 0.01871 0.02547 = 0.02186 0.00086 -0.00499 -0.01302 AFIX 43 H3 2 0.260806 0.522074 0.280657 11.00000 -1.20000 AFIX 0 C11 1 0.360023 0.814439 0.082517 11.00000 0.01650 0.02023 = 0.02470 0.00078 -0.00790 -0.00414 AFIX 43 H11 2 0.300867 0.916857 0.051770 11.00000 -1.20000 AFIX 0 C9 1 0.721112 -0.249875 0.351538 11.00000 0.01856 0.01708 = 0.02377 -0.00103 -0.00448 -0.00593 AFIX 43 H9 2 0.827799 -0.335317 0.352305 11.00000 -1.20000 AFIX 0 C10 1 0.740092 -0.103222 0.282890 11.00000 0.01555 0.01773 = 0.01507 -0.00203 -0.00415 -0.00686 C8 1 0.550927 -0.268200 0.416024 11.00000 0.02479 0.02186 = 0.02226 -0.00190 -0.00276 -0.01277 AFIX 43 H8 2 0.540723 -0.367162 0.460227 11.00000 -1.20000 AFIX 0 C7 1 0.405388 -0.005621 0.358559 11.00000 0.01514 0.02802 = 0.02306 -0.00588 -0.00579 -0.00299 AFIX 43 H7 2 0.295047 0.077752 0.362785 11.00000 -1.20000 AFIX 0 C2 1 0.523509 0.517894 0.174280 11.00000 0.01854 0.01722 = 0.02160 0.00178 -0.00731 -0.00782 AFIX 43 H2 2 0.576938 0.414571 0.206899 11.00000 -1.20000 AFIX 0 C1 1 0.640874 0.604912 0.079686 11.00000 0.01447 0.01684 = 0.01622 -0.00089 -0.00503 -0.00595 LI1 3 0.986860 0.382266 0.111754 11.00000 0.01637 0.01947 = 0.02205 0.00210 -0.00547 -0.00514 HKLF 4 REM 2_a.res in P-1 REM wR2 = 0.1127, GooF = S = 1.022, Restrained GooF = 1.025 for all data REM R1 = 0.0404 for 2802 Fo > 4sig(Fo) and 0.0453 for all 3158 data REM 184 parameters refined using 1 restraints END WGHT 0.0635 0.1737 REM Highest difference peak 0.434, deepest hole -0.230, 1-sigma level 0.050 Q1 1 0.5940 0.6846 0.0542 11.00000 0.05 0.43 Q2 1 0.6530 -0.0433 0.2889 11.00000 0.05 0.37 Q3 1 0.4529 0.7875 0.0732 11.00000 0.05 0.37 Q4 1 0.7328 -0.1750 0.3139 11.00000 0.05 0.33 Q5 1 0.3064 0.6496 0.1822 11.00000 0.05 0.33 ; _shelx_res_checksum 59905 _olex2_submission_special_instructions 'No special instructions were received' 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 O5 O 0.80197(13) 0.35259(12) 0.35094(11) 0.0297(2) Uani 1 1 d . . . . . O6 O 1.00862(14) 0.16930(10) 0.07298(10) 0.0258(2) Uani 1 1 d G . . . . H6A H 0.953665 0.104479 0.129638 0.039 Uiso 1 1 d DG U . . . H6B H 1.026425 0.144261 -0.014062 0.039 Uiso 1 1 d DG U . . . O2 O 0.89818(11) -0.08373(10) 0.21526(9) 0.02087(19) Uani 1 1 d . . . . . O1 O 0.81610(11) 0.54992(10) 0.03903(9) 0.01951(19) Uani 1 1 d . . . . . O7 O 0.95669(13) 0.21528(13) 0.48617(10) 0.0323(2) Uani 1 1 d . . . . . O3 O 1.08853(13) 0.33392(12) 0.28984(10) 0.0299(2) Uani 1 1 d . . . . . N3 N 0.94939(14) 0.30077(12) 0.37710(10) 0.0199(2) Uani 1 1 d . . . . . N4 N 0.25572(13) 0.72844(12) 0.17353(11) 0.0211(2) Uani 1 1 d . . . . . H4 H 0.134562 0.768255 0.204093 0.025 Uiso 1 1 calc R U . . . N2 N 0.39601(14) -0.14835(13) 0.41845(11) 0.0236(2) Uani 1 1 d . . . . . H2A H 0.287740 -0.163708 0.459631 0.028 Uiso 1 1 calc R U . . . C6 C 0.57179(16) 0.02004(13) 0.29203(12) 0.0196(2) Uani 1 1 d . . . . . H6 H 0.575823 0.121529 0.251099 0.024 Uiso 1 1 calc R U . . . C5 C 0.54824(15) 0.75770(13) 0.03373(12) 0.0188(2) Uani 1 1 d . . . . . H5 H 0.618132 0.820162 -0.031178 0.023 Uiso 1 1 calc R U . . . C3 C 0.33610(16) 0.58170(15) 0.21797(13) 0.0211(2) Uani 1 1 d . . . . . H3 H 0.260806 0.522074 0.280657 0.025 Uiso 1 1 calc R U . . . C11 C 0.36002(16) 0.81444(14) 0.08252(13) 0.0208(2) Uani 1 1 d . . . . . H11 H 0.300867 0.916857 0.051770 0.025 Uiso 1 1 calc R U . . . C9 C 0.72111(16) -0.24988(14) 0.35154(13) 0.0205(2) Uani 1 1 d . . . . . H9 H 0.827799 -0.335317 0.352305 0.025 Uiso 1 1 calc R U . . . C10 C 0.74009(15) -0.10322(13) 0.28289(11) 0.0158(2) Uani 1 1 d . . . . . C8 C 0.55093(17) -0.26820(15) 0.41602(13) 0.0229(3) Uani 1 1 d . . . . . H8 H 0.540723 -0.367162 0.460227 0.028 Uiso 1 1 calc R U . . . C7 C 0.40539(16) -0.00562(15) 0.35856(13) 0.0228(2) Uani 1 1 d . . . . . H7 H 0.295047 0.077752 0.362785 0.027 Uiso 1 1 calc R U . . . C2 C 0.52351(16) 0.51789(13) 0.17428(12) 0.0186(2) Uani 1 1 d . . . . . H2 H 0.576938 0.414571 0.206899 0.022 Uiso 1 1 calc R U . . . C1 C 0.64087(15) 0.60491(13) 0.07969(11) 0.0156(2) Uani 1 1 d . . . . . Li1 Li 0.9869(3) 0.3823(2) 0.1118(2) 0.0200(4) Uani 1 1 d D . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O5 0.0212(4) 0.0321(5) 0.0348(5) 0.0047(4) -0.0130(4) -0.0056(4) O6 0.0350(5) 0.0202(4) 0.0226(4) 0.0012(3) -0.0057(4) -0.0146(4) O2 0.0145(4) 0.0230(4) 0.0237(4) 0.0015(3) -0.0030(3) -0.0087(3) O1 0.0120(4) 0.0197(4) 0.0225(4) 0.0036(3) -0.0038(3) -0.0035(3) O7 0.0241(5) 0.0449(6) 0.0233(4) 0.0137(4) -0.0077(4) -0.0114(4) O3 0.0258(5) 0.0395(5) 0.0258(5) 0.0048(4) -0.0027(4) -0.0208(4) N3 0.0182(5) 0.0207(5) 0.0185(5) 0.0002(4) -0.0035(4) -0.0065(4) N4 0.0119(4) 0.0264(5) 0.0246(5) -0.0019(4) -0.0051(4) -0.0063(4) N2 0.0154(5) 0.0330(6) 0.0226(5) -0.0065(4) -0.0007(4) -0.0123(4) C6 0.0189(5) 0.0176(5) 0.0213(5) -0.0005(4) -0.0072(4) -0.0039(4) C5 0.0163(5) 0.0173(5) 0.0219(5) 0.0028(4) -0.0057(4) -0.0064(4) C3 0.0187(5) 0.0255(6) 0.0219(5) 0.0009(4) -0.0050(4) -0.0130(5) C11 0.0165(5) 0.0202(5) 0.0247(6) 0.0008(4) -0.0079(4) -0.0041(4) C9 0.0186(5) 0.0171(5) 0.0238(5) -0.0010(4) -0.0045(4) -0.0059(4) C10 0.0156(5) 0.0177(5) 0.0151(5) -0.0020(4) -0.0041(4) -0.0069(4) C8 0.0248(6) 0.0219(6) 0.0223(5) -0.0019(4) -0.0028(5) -0.0128(5) C7 0.0151(5) 0.0280(6) 0.0231(5) -0.0059(4) -0.0058(4) -0.0030(4) C2 0.0185(5) 0.0172(5) 0.0216(5) 0.0018(4) -0.0073(4) -0.0078(4) C1 0.0145(5) 0.0168(5) 0.0162(5) -0.0009(4) -0.0050(4) -0.0060(4) Li1 0.0164(9) 0.0195(9) 0.0220(9) 0.0021(7) -0.0055(7) -0.0051(7) 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' N N 0.0061 0.0033 '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' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 -1.00 -1.00 0.0730 0.00 1.00 1.00 0.1490 0.00 1.00 -1.00 0.1030 -1.00 1.00 0.00 0.1360 1.00 0.00 -1.00 0.0780 1.00 0.00 0.00 0.1010 -1.00 0.00 0.00 0.1240 1.00 0.00 1.00 0.1470 -1.00 0.00 -1.00 0.1110 1.00 1.00 -1.00 0.0850 -1.00 -1.00 1.00 0.0530 0.00 0.00 -1.00 0.0810 0.00 0.00 1.00 0.1130 0.00 1.00 0.00 0.1440 0.00 -1.00 0.00 0.0590 -1.00 1.00 1.00 0.1350 1.00 -1.00 -1.00 0.0800 1.00 1.00 0.00 0.1050 -1.00 -1.00 -1.00 0.0620 1.00 1.00 1.00 0.1050 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 N3 O5 Li1 85.91(8) . . ? H6A O6 H6B 104.5 . . ? Li1 O6 H6A 128.7 . . ? Li1 O6 H6B 119.9 . . ? C1 O1 Li1 133.77(9) . . ? C1 O1 Li1 132.47(9) . 2_765 ? Li1 O1 Li1 93.57(8) . 2_765 ? N3 O3 Li1 93.95(9) . . ? O5 N3 O3 118.52(10) . . ? O5 N3 Li1 64.99(8) . . ? O7 N3 O5 120.07(10) . . ? O7 N3 O3 121.40(10) . . ? O7 N3 Li1 160.13(10) . . ? O3 N3 Li1 56.92(7) . . ? C3 N4 H4 119.7 . . ? C11 N4 H4 119.7 . . ? C11 N4 C3 120.51(10) . . ? C8 N2 H2A 119.6 . . ? C7 N2 H2A 119.6 . . ? C7 N2 C8 120.85(10) . . ? C10 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C7 C6 C10 121.03(11) . . ? C11 C5 H5 119.8 . . ? C11 C5 C1 120.40(10) . . ? C1 C5 H5 119.8 . . ? N4 C3 H3 119.5 . . ? N4 C3 C2 121.07(11) . . ? C2 C3 H3 119.5 . . ? N4 C11 C5 121.59(11) . . ? N4 C11 H11 119.2 . . ? C5 C11 H11 119.2 . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C8 C9 C10 120.35(11) . . ? O2 C10 C6 122.01(10) . . ? O2 C10 C9 122.19(10) . . ? C9 C10 C6 115.79(10) . . ? N2 C8 C9 121.35(11) . . ? N2 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? N2 C7 C6 120.59(11) . . ? N2 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C3 C2 H2 119.6 . . ? C3 C2 C1 120.78(11) . . ? C1 C2 H2 119.6 . . ? O1 C1 C5 122.05(10) . . ? O1 C1 C2 122.33(10) . . ? C5 C1 C2 115.62(10) . . ? O5 Li1 N3 29.10(4) . . ? O5 Li1 Li1 139.64(12) . 2_765 ? O6 Li1 O5 89.33(8) . . ? O6 Li1 O1 114.87(11) . . ? O6 Li1 O1 109.61(10) . 2_765 ? O6 Li1 O3 99.86(9) . . ? O6 Li1 N3 89.48(8) . . ? O6 Li1 Li1 121.23(13) . 2_765 ? O1 Li1 O5 102.04(9) . . ? O1 Li1 O5 153.95(11) 2_765 . ? O1 Li1 O1 86.43(8) . 2_765 ? O1 Li1 O3 100.79(9) 2_765 . ? O1 Li1 O3 139.89(11) . . ? O1 Li1 N3 129.86(10) 2_765 . ? O1 Li1 N3 127.72(10) . . ? O1 Li1 Li1 43.49(6) . 2_765 ? O1 Li1 Li1 42.94(6) 2_765 2_765 ? O3 Li1 O5 57.14(6) . . ? O3 Li1 N3 29.12(4) . . ? O3 Li1 Li1 130.63(13) . 2_765 ? N3 Li1 Li1 149.27(13) . 2_765 ? 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 O5 N3 1.2521(13) . ? O5 Li1 2.333(2) . ? O6 H6A 0.8702 . ? O6 H6B 0.8697 . ? O6 Li1 1.935(2) . ? O2 C10 1.2813(13) . ? O1 C1 1.2726(13) . ? O1 Li1 1.942(2) . ? O1 Li1 1.962(2) 2_765 ? O7 N3 1.2462(13) . ? O3 N3 1.2529(13) . ? O3 Li1 2.157(2) . ? N3 Li1 2.568(2) . ? N4 H4 0.8800 . ? N4 C3 1.3521(16) . ? N4 C11 1.3515(15) . ? N2 H2A 0.8800 . ? N2 C8 1.3530(17) . ? N2 C7 1.3490(17) . ? C6 H6 0.9500 . ? C6 C10 1.4276(15) . ? C6 C7 1.3632(16) . ? C5 H5 0.9500 . ? C5 C11 1.3644(15) . ? C5 C1 1.4289(15) . ? C3 H3 0.9500 . ? C3 C2 1.3638(16) . ? C11 H11 0.9500 . ? C9 H9 0.9500 . ? C9 C10 1.4249(15) . ? C9 C8 1.3613(16) . ? C8 H8 0.9500 . ? C7 H7 0.9500 . ? C2 H2 0.9500 . ? C2 C1 1.4340(15) . ? Li1 Li1 2.845(4) 2_765 ? 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 _geom_hbond_publ_flag O6 H6A O2 0.87 1.90 2.7432(12) 162.3 . yes O6 H6B O2 0.87 1.96 2.8194(12) 172.2 2_755 yes N4 H4 O2 0.88 1.92 2.7503(13) 157.4 1_465 yes N2 H2A O5 0.88 2.43 3.0565(14) 128.8 2_656 yes N2 H2A O7 0.88 2.07 2.9381(14) 168.0 2_656 yes 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 N4 C3 C2 C1 -0.01(18) . . . . ? C3 N4 C11 C5 -0.65(18) . . . . ? C3 C2 C1 O1 178.71(10) . . . . ? C3 C2 C1 C5 -1.35(16) . . . . ? C11 N4 C3 C2 1.06(18) . . . . ? C11 C5 C1 O1 -178.32(11) . . . . ? C11 C5 C1 C2 1.74(16) . . . . ? C10 C6 C7 N2 0.50(18) . . . . ? C10 C9 C8 N2 -0.81(18) . . . . ? C8 N2 C7 C6 1.12(18) . . . . ? C8 C9 C10 O2 -176.68(11) . . . . ? C8 C9 C10 C6 2.28(16) . . . . ? C7 N2 C8 C9 -0.97(18) . . . . ? C7 C6 C10 O2 176.82(11) . . . . ? C7 C6 C10 C9 -2.14(16) . . . . ? C1 C5 C11 N4 -0.81(18) . . . . ? Li1 O5 N3 O7 -158.29(12) . . . . ? Li1 O5 N3 O3 20.12(11) . . . . ? Li1 O1 C1 C5 -12.33(18) 2_765 . . . ? Li1 O1 C1 C5 161.26(12) . . . . ? Li1 O1 C1 C2 -18.81(19) . . . . ? Li1 O1 C1 C2 167.61(12) 2_765 . . . ? Li1 O3 N3 O5 -21.84(12) . . . . ? Li1 O3 N3 O7 156.54(12) . . . . ?