#------------------------------------------------------------------------------ #$Date: 2020-05-22 04:35:48 +0300 (Fri, 22 May 2020) $ #$Revision: 252267 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240566.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_7240566 loop_ _publ_author_name 'Marek, Paulina Halina' 'Cichowicz, Grzegorz' 'Osowicka, Dorota' 'Madura, Izabela Dorota' 'Dobrzycki, Lukasz' 'Cyranski, Michal' 'Ciesielski, Arkadiusz' _publ_section_title ; Polymorphism and structural diversities of LiClO4 - \b-alanine ionic co-crystals ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D0CE00592D _journal_year 2020 _chemical_absolute_configuration ad _chemical_formula_moiety 'C6 H14 Li N2 O4, Cl O4' _chemical_formula_sum 'C6 H14 Cl Li N2 O8' _chemical_formula_weight 284.58 _chemical_name_systematic 'catena-(bis(/m-2-beta-Alanine)-lithium perchlorate)' _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens mixed _audit_creation_date 2019-07-09 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2020-04-08 deposited with the CCDC. 2020-05-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 95.899(4) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 4.9667(6) _cell_length_b 8.4410(11) _cell_length_c 13.9410(18) _cell_measurement_reflns_used 9886 _cell_measurement_temperature 100.0(5) _cell_measurement_theta_max 30.53 _cell_measurement_theta_min 2.41 _cell_volume 581.37(13) _computing_cell_refinement 'SAINT V8.38A (Bruker Nano, Inc., 2016)' _computing_data_collection 'APEX3 V2019 (Bruker Nano, Inc., 2019)' _computing_data_reduction 'SAINT V8.38A (Bruker Nano, Inc., 2016)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'XT (Sheldrick, 2015)' _diffrn_ambient_temperature 100.0(5) _diffrn_detector_area_resol_mean 7.3910 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker D8 VENTURE' _diffrn_measurement_method '\o and \f scans' _diffrn_radiation_monochromator TRIUMPH _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0459 _diffrn_reflns_av_unetI/netI 0.0313 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 17343 _diffrn_reflns_theta_full 30.56 _diffrn_reflns_theta_max 30.56 _diffrn_reflns_theta_min 2.83 _diffrn_source 'fine focus sealed tube' _exptl_absorpt_coefficient_mu 0.364 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_correction_T_min 0.6959 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0731 before and 0.0675 after correction. The Ratio of minimum to maximum transmission is 0.9327. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.626 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 296 _exptl_crystal_size_max 0.290 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.130 _refine_diff_density_max 0.238 _refine_diff_density_min -0.291 _refine_ls_abs_structure_details ; Flack x determined using 1576 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.04(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 229 _refine_ls_number_reflns 3541 _refine_ls_number_restraints 38 _refine_ls_restrained_S_all 1.088 _refine_ls_R_factor_all 0.0264 _refine_ls_R_factor_gt 0.0258 _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^)+(0.0313P)^2^+0.0991P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0644 _refine_ls_wR_factor_ref 0.0648 _reflns_number_gt 3477 _reflns_number_total 3541 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00592d2.cif _cod_data_source_block 2 _cod_database_code 7240566 _shelx_shelxl_version_number 2018/3 _shelx_estimated_absorpt_t_max 0.954 _shelx_estimated_absorpt_t_min 0.902 _shelx_res_file ; TITL 2-1-new in P2(1) 2-1-new.res created by SHELXL-2018/3 at 23:50:04 on 05-Apr-2020 CELL 0.71073 4.9667 8.441 13.941 90 95.899 90 ZERR 2 0.0006 0.0011 0.0018 0 0.004 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H Cl Li N O UNIT 12 28 2 2 4 16 L.S. 10 PLAN 2 SIZE 0.13 0.15 0.29 TEMP -173.22 BOND $H LIST 4 htab EQIV $1 -x+1, y+1/2, -z+1 EQIV $2 x-1, y, z EQIV $3 -x, y+1/2, -z+1 EQIV $4 -x+1, y-1/2, -z+2 EQIV $5 x, y-1, z HTAB N1 O6 HTAB N1 O3 HTAB N1 O4_$2 HTAB N1 O2_$3 HTAB N11 O16_$2 HTAB N11 O15_$4 HTAB N11 O16 HTAB N11 O5_$5 conf fmap 2 exyz cl1 cl1b eadp cl1 cl1b exyz cl1b cl1c eadp cl1b cl1c exyz o4 o4b exyz o4b o4c eadp o4 o4b eadp o4b o4c isor 0.005 o3c sump 1 0.0001 1 2 1 3 1 4 acta WGHT 0.031300 0.099100 FVAR 1.69035 0.66172 0.09095 0.24730 C1 1 -0.059806 0.814375 0.801195 11.00000 0.00843 0.00707 = 0.00988 0.00098 -0.00113 -0.00090 C2 1 -0.216832 0.723633 0.719050 11.00000 0.01044 0.01405 = 0.01048 -0.00220 0.00003 -0.00229 AFIX 23 H2A 2 -0.271202 0.619507 0.743458 11.00000 -1.20000 H2B 2 -0.383940 0.782958 0.697256 11.00000 -1.20000 AFIX 0 C3 1 -0.056199 0.697396 0.633513 11.00000 0.01574 0.01197 = 0.01114 -0.00089 0.00094 -0.00009 AFIX 23 H3A 2 0.110963 0.637429 0.654309 11.00000 -1.20000 H3B 2 -0.164970 0.634512 0.583624 11.00000 -1.20000 AFIX 0 C11 1 0.456254 0.426223 0.915102 11.00000 0.00985 0.00871 = 0.00854 -0.00103 0.00309 0.00051 C12 1 0.195815 0.385965 0.852539 11.00000 0.01057 0.00986 = 0.01349 0.00207 -0.00144 -0.00065 AFIX 23 H12A 2 0.043628 0.440138 0.879499 11.00000 -1.20000 H12B 2 0.208016 0.429303 0.787140 11.00000 -1.20000 AFIX 0 C13 1 0.130194 0.210601 0.843446 11.00000 0.01584 0.01073 = 0.01002 -0.00079 0.00128 -0.00400 AFIX 23 H13A 2 -0.016900 0.194927 0.790778 11.00000 -1.20000 H13B 2 0.291700 0.152880 0.826000 11.00000 -1.20000 AFIX 0 part 1 21 CL1 3 0.516756 0.728297 0.390526 21.00000 0.01061 0.02079 = 0.01145 -0.00179 0.00152 0.00135 O1 6 0.398512 0.830132 0.314105 21.00000 0.02563 0.02286 = 0.02306 0.00700 -0.00503 -0.00001 O2 6 0.420539 0.572380 0.373019 21.00000 0.04230 0.01787 = 0.06452 0.00264 0.02159 -0.00789 O3 6 0.444431 0.788951 0.481444 21.00000 0.01906 0.06609 = 0.01271 -0.01021 0.00065 0.01285 O4 6 0.806828 0.729733 0.395025 21.00000 0.01238 0.05450 = 0.02105 -0.00685 0.00086 0.00259 part 2 31 same cl1 o1 o2 o3 o4 CL1B 3 0.516756 0.728297 0.390526 31.00000 0.01061 0.02079 = 0.01145 -0.00179 0.00152 0.00135 O1B 6 0.383249 0.769767 0.302719 31.00000 0.01688 O2B 6 0.441817 0.568491 0.421481 31.00000 0.02779 O3B 6 0.445123 0.836734 0.466811 31.00000 0.01491 O4B 6 0.806828 0.729733 0.395025 31.00000 0.01238 0.05450 = 0.02105 -0.00685 0.00086 0.00259 part 3 41 same cl1 o1 o2 o3 o4 CL1C 3 0.516756 0.728297 0.390526 41.00000 0.01061 0.02079 = 0.01145 -0.00179 0.00152 0.00135 O1C 6 0.413250 0.857389 0.335659 41.00000 0.03761 0.01034 = 0.02813 -0.00457 -0.01374 0.00361 O2C 6 0.434036 0.574868 0.344643 41.00000 0.02533 0.01670 = 0.02871 -0.00572 0.00549 -0.00978 O3C 6 0.416668 0.721087 0.485858 41.00000 0.02392 0.05875 = 0.01450 0.00567 0.01055 0.02072 O4C 6 0.806828 0.729733 0.395025 41.00000 0.01238 0.05450 = 0.02105 -0.00685 0.00086 0.00259 part 0 LI1 4 0.463623 0.784237 0.895332 11.00000 0.01092 0.01243 = 0.01190 -0.00151 0.00117 -0.00091 N1 5 0.015732 0.853890 0.592239 11.00000 0.01625 0.01770 = 0.01266 0.00101 0.00432 0.00009 H1A 2 0.127138 0.902543 0.632228 11.00000 0.02729 H1B 2 0.105387 0.838719 0.540013 11.00000 0.03227 H1C 2 -0.124385 0.906489 0.577035 11.00000 0.02461 N11 5 0.045063 0.142855 0.934591 11.00000 0.01009 0.00827 = 0.01189 -0.00053 0.00065 -0.00047 H11A 2 -0.094492 0.201591 0.953058 11.00000 0.01834 H11B 2 0.183031 0.130991 0.979222 11.00000 0.02040 H11C 2 -0.013403 0.048520 0.922486 11.00000 0.01705 O5 6 -0.186781 0.858108 0.870497 11.00000 0.01047 0.01289 = 0.01125 -0.00268 0.00277 -0.00372 O6 6 0.186542 0.841667 0.795294 11.00000 0.00742 0.01740 = 0.01278 0.00034 0.00035 -0.00071 O15 6 0.543740 0.564915 0.910420 11.00000 0.01895 0.00912 = 0.01678 -0.00069 -0.00246 -0.00271 O16 6 0.570066 0.319482 0.968442 11.00000 0.01065 0.01301 = 0.01033 0.00256 0.00181 0.00262 HKLF 4 REM 2-1-new in P2(1) REM wR2 = 0.064759, GooF = S = 1.08124, Restrained GooF = 1.08805 for all data REM R1 = 0.025807 for 3477 Fo > 4sig(Fo) and 0.026449 for all 3541 data REM 229 parameters refined using 38 restraints END WGHT 0.0313 0.0991 REM Instructions for potential hydrogen bonds EQIV $8 -x, y-1/2, -z+1 HTAB C2 O1_$8 HTAB C2 O1C_$8 HTAB C2 O15_$2 HTAB C2 O2_$3 HTAB C2 O2C_$3 HTAB C3 O3_$2 HTAB C3 O3C_$2 HTAB C13 O1_$8 HTAB C13 O1B_$8 HTAB N1 O2C_$1 HTAB N1 O6 HTAB N1 O3 HTAB N1 O4_$2 HTAB N1 O3B HTAB N1 O3C HTAB N1 O2_$3 HTAB N1 O3_$2 HTAB N1 O2B_$3 HTAB N1 O3B_$2 HTAB N1 O2C_$3 HTAB N11 O16_$2 HTAB N11 O15_$4 HTAB N11 O16 HTAB N11 O5_$5 REM Highest difference peak 0.238, deepest hole -0.291, 1-sigma level 0.055 Q1 1 1.1068 0.7253 0.3969 11.00000 0.05 0.24 Q2 1 0.1567 0.3020 0.8518 11.00000 0.05 0.23 ; _shelx_res_checksum 96543 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_flags_posn _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C C1 -0.0598(3) 0.81438(17) 0.80119(11) 0.0086(3) Uani d . . . 1.0 . . C C2 -0.2168(3) 0.7236(2) 0.71905(10) 0.0117(3) Uani d . . . 1.0 . . H H2A -0.271202 0.619507 0.743458 0.014 Uiso calc U . R 1.0 . . H H2B -0.38394 0.782958 0.697256 0.014 Uiso calc U . R 1.0 . . C C3 -0.0562(4) 0.69740(19) 0.63351(12) 0.0130(3) Uani d . . . 1.0 . . H H3A 0.110963 0.637429 0.654309 0.016 Uiso calc U . R 1.0 . . H H3B -0.16497 0.634512 0.583624 0.016 Uiso calc U . R 1.0 . . C C11 0.4563(3) 0.42622(18) 0.91510(11) 0.0089(3) Uani d . . . 1.0 . . C C12 0.1958(3) 0.3860(2) 0.85254(12) 0.0115(3) Uani d . . . 1.0 . . H H12A 0.043628 0.440138 0.879499 0.014 Uiso calc U . R 1.0 . . H H12B 0.208016 0.429303 0.78714 0.014 Uiso calc U . R 1.0 . . C C13 0.1302(3) 0.2106(2) 0.84345(11) 0.0122(3) Uani d . . . 1.0 . . H H13A -0.0169 0.194927 0.790778 0.015 Uiso calc U . R 1.0 . . H H13B 0.2917 0.15288 0.826 0.015 Uiso calc U . R 1.0 . . Cl Cl1 0.51676(7) 0.72830(5) 0.39053(3) 0.01425(9) Uani d . P D 0.662(4) A 1 O O1 0.3985(14) 0.8301(8) 0.3141(4) 0.0244(12) Uani d . P D 0.662(4) A 1 O O2 0.4205(19) 0.5724(8) 0.3730(6) 0.040(2) Uani d . P D 0.662(4) A 1 O O3 0.4444(9) 0.7890(8) 0.4814(3) 0.0327(15) Uani d . P D 0.662(4) A 1 O O4 0.8068(3) 0.7297(3) 0.39502(10) 0.0294(3) Uani d . P D 0.662(4) A 1 Cl Cl1B 0.51676(7) 0.72830(5) 0.39053(3) 0.01425(9) Uani d . P D 0.091(4) B 2 O O1B 0.383(4) 0.770(2) 0.3027(12) 0.017(5) Uiso d . P D 0.091(4) B 2 O O2B 0.442(4) 0.568(2) 0.4215(17) 0.028(5) Uiso d . P D 0.091(4) B 2 O O3B 0.445(6) 0.837(3) 0.4668(16) 0.015(5) Uiso d . P D 0.091(4) B 2 O O4B 0.8068(3) 0.7297(3) 0.39502(10) 0.0294(3) Uani d . P D 0.091(4) B 2 Cl Cl1C 0.51676(7) 0.72830(5) 0.39053(3) 0.01425(9) Uani d . P D 0.247(4) C 3 O O1C 0.413(5) 0.8574(19) 0.3357(11) 0.027(3) Uani d . P D 0.247(4) C 3 O O2C 0.434(4) 0.575(2) 0.3446(12) 0.023(3) Uani d . P D 0.247(4) C 3 O O3C 0.417(3) 0.7211(16) 0.4859(9) 0.032(3) Uani d U P D 0.247(4) C 3 O O4C 0.8068(3) 0.7297(3) 0.39502(10) 0.0294(3) Uani d . P D 0.247(4) C 3 Li Li1 0.4636(6) 0.7842(4) 0.8953(2) 0.0117(5) Uani d . . . 1.0 . . N N1 0.0157(3) 0.8539(2) 0.59224(11) 0.0153(3) Uani d . . . 1.0 . . H H1A 0.127(6) 0.903(4) 0.632(2) 0.027(8) Uiso d . . . 1.0 . . H H1B 0.105(6) 0.839(4) 0.540(2) 0.032(8) Uiso d . . . 1.0 . . H H1C -0.124(6) 0.906(4) 0.577(2) 0.025(7) Uiso d . . . 1.0 . . N N11 0.0451(3) 0.14285(17) 0.93459(10) 0.0101(2) Uani d . . . 1.0 . . H H11A -0.094(5) 0.202(3) 0.9531(19) 0.018(6) Uiso d . . . 1.0 . . H H11B 0.183(6) 0.131(4) 0.979(2) 0.020(6) Uiso d . . . 1.0 . . H H11C -0.013(6) 0.049(3) 0.9225(19) 0.017(6) Uiso d . . . 1.0 . . O O5 -0.1868(2) 0.85811(15) 0.87050(8) 0.0114(2) Uani d . . . 1.0 . . O O6 0.1865(2) 0.84167(16) 0.79529(9) 0.0126(2) Uani d . . . 1.0 . . O O15 0.5437(3) 0.56492(15) 0.91042(10) 0.0152(2) Uani d . . . 1.0 . . O O16 0.5701(2) 0.31948(14) 0.96844(9) 0.0113(2) Uani d . . . 1.0 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0084(6) 0.0071(6) 0.0099(6) -0.0009(5) -0.0011(5) 0.0010(5) C2 0.0104(6) 0.0141(6) 0.0105(6) -0.0023(6) 0.0000(5) -0.0022(6) C3 0.0157(7) 0.0120(7) 0.0111(6) -0.0001(5) 0.0009(5) -0.0009(5) C11 0.0098(7) 0.0087(6) 0.0085(6) 0.0005(5) 0.0031(5) -0.0010(5) C12 0.0106(7) 0.0099(6) 0.0135(7) -0.0007(5) -0.0014(5) 0.0021(5) C13 0.0158(7) 0.0107(7) 0.0100(6) -0.0040(6) 0.0013(5) -0.0008(6) Cl1 0.01061(16) 0.02079(18) 0.01145(15) 0.00135(15) 0.00152(11) -0.00179(16) O1 0.0256(17) 0.023(3) 0.023(2) 0.000(2) -0.0050(17) 0.007(2) O2 0.042(2) 0.0179(17) 0.065(6) -0.0079(14) 0.022(4) 0.003(3) O3 0.0191(17) 0.066(5) 0.0127(17) 0.013(3) 0.0007(13) -0.010(3) O4 0.0124(6) 0.0545(10) 0.0210(6) 0.0026(8) 0.0009(5) -0.0069(8) Cl1B 0.01061(16) 0.02079(18) 0.01145(15) 0.00135(15) 0.00152(11) -0.00179(16) O4B 0.0124(6) 0.0545(10) 0.0210(6) 0.0026(8) 0.0009(5) -0.0069(8) Cl1C 0.01061(16) 0.02079(18) 0.01145(15) 0.00135(15) 0.00152(11) -0.00179(16) O1C 0.038(5) 0.010(4) 0.028(7) 0.004(4) -0.014(5) -0.005(4) O2C 0.025(5) 0.017(4) 0.029(6) -0.010(3) 0.005(4) -0.006(4) O3C 0.024(5) 0.059(8) 0.014(3) 0.021(5) 0.011(3) 0.006(5) O4C 0.0124(6) 0.0545(10) 0.0210(6) 0.0026(8) 0.0009(5) -0.0069(8) Li1 0.0109(12) 0.0124(12) 0.0119(12) -0.0009(10) 0.0012(10) -0.0015(10) N1 0.0162(7) 0.0177(7) 0.0127(6) 0.0001(6) 0.0043(5) 0.0010(5) N11 0.0101(6) 0.0083(6) 0.0119(6) -0.0005(5) 0.0007(5) -0.0005(5) O5 0.0105(5) 0.0129(5) 0.0113(5) -0.0037(4) 0.0028(4) -0.0027(4) O6 0.0074(5) 0.0174(6) 0.0128(5) -0.0007(4) 0.0004(4) 0.0003(4) O15 0.0189(6) 0.0091(5) 0.0168(5) -0.0027(4) -0.0025(5) -0.0007(4) O16 0.0106(5) 0.0130(5) 0.0103(5) 0.0026(4) 0.0018(4) 0.0026(4) 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' Cl Cl 0.1484 0.1585 '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_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O6 C1 O5 . . 124.28(15) ? O6 C1 C2 . . 118.01(14) ? O5 C1 C2 . . 117.70(14) ? C3 C2 C1 . . 113.20(13) ? C3 C2 H2A . . 108.9 ? C1 C2 H2A . . 108.9 ? C3 C2 H2B . . 108.9 ? C1 C2 H2B . . 108.9 ? H2A C2 H2B . . 107.8 ? N1 C3 C2 . . 109.78(14) ? N1 C3 H3A . . 109.7 ? C2 C3 H3A . . 109.7 ? N1 C3 H3B . . 109.7 ? C2 C3 H3B . . 109.7 ? H3A C3 H3B . . 108.2 ? O15 C11 O16 . . 124.07(16) ? O15 C11 C12 . . 117.23(14) ? O16 C11 C12 . . 118.70(14) ? C13 C12 C11 . . 115.34(13) ? C13 C12 H12A . . 108.4 ? C11 C12 H12A . . 108.4 ? C13 C12 H12B . . 108.4 ? C11 C12 H12B . . 108.4 ? H12A C12 H12B . . 107.5 ? N11 C13 C12 . . 112.30(13) ? N11 C13 H13A . . 109.1 ? C12 C13 H13A . . 109.1 ? N11 C13 H13B . . 109.1 ? C12 C13 H13B . . 109.1 ? H13A C13 H13B . . 107.9 ? O2 Cl1 O4 . . 109.6(4) ? O2 Cl1 O1 . . 108.8(5) ? O4 Cl1 O1 . . 110.9(3) ? O2 Cl1 O3 . . 111.8(3) ? O4 Cl1 O3 . . 107.3(2) ? O1 Cl1 O3 . . 108.5(3) ? O1B Cl1B O4B . . 115.2(8) ? O1B Cl1B O3B . . 110.7(13) ? O4B Cl1B O3B . . 106.2(12) ? O1B Cl1B O2B . . 112.3(11) ? O4B Cl1B O2B . . 106.1(9) ? O3B Cl1B O2B . . 105.7(14) ? O1C Cl1C O4C . . 109.2(10) ? O1C Cl1C O3C . . 112.8(10) ? O4C Cl1C O3C . . 113.1(6) ? O1C Cl1C O2C . . 112.0(10) ? O4C Cl1C O2C . . 105.0(8) ? O3C Cl1C O2C . . 104.5(8) ? O15 Li1 O5 . 1_655 98.87(15) ? O15 Li1 O6 . . 116.94(16) ? O5 Li1 O6 1_655 . 112.55(16) ? O15 Li1 O16 . 2_657 94.53(15) ? O5 Li1 O16 1_655 2_657 107.33(15) ? O6 Li1 O16 . 2_657 122.93(17) ? C3 N1 H1A . . 110.(2) ? C3 N1 H1B . . 110.(2) ? H1A N1 H1B . . 105.(3) ? C3 N1 H1C . . 110.(2) ? H1A N1 H1C . . 112.(3) ? H1B N1 H1C . . 110.(3) ? C13 N11 H11A . . 108.8(17) ? C13 N11 H11B . . 112.1(18) ? H11A N11 H11B . . 115.(2) ? C13 N11 H11C . . 107.9(18) ? H11A N11 H11C . . 108.(3) ? H11B N11 H11C . . 105.(3) ? C1 O5 Li1 . 1_455 125.34(14) ? C1 O6 Li1 . . 122.48(14) ? C11 O15 Li1 . . 147.80(15) ? C11 O16 Li1 . 2_647 127.22(14) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 O6 . 1.2560(19) ? C1 O5 . 1.2620(19) ? C1 C2 . 1.524(2) ? C2 C3 . 1.518(2) ? C2 H2A . 0.99 ? C2 H2B . 0.99 ? C3 N1 . 1.499(2) ? C3 H3A . 0.99 ? C3 H3B . 0.99 ? C11 O15 . 1.253(2) ? C11 O16 . 1.2641(19) ? C11 C12 . 1.522(2) ? C12 C13 . 1.518(2) ? C12 H12A . 0.99 ? C12 H12B . 0.99 ? C13 N11 . 1.494(2) ? C13 H13A . 0.99 ? C13 H13B . 0.99 ? Cl1 O2 . 1.413(6) ? Cl1 O4 . 1.4357(14) ? Cl1 O1 . 1.446(5) ? Cl1 O3 . 1.446(4) ? Cl1B O1B . 1.376(15) ? Cl1B O4B . 1.4357(14) ? Cl1B O3B . 1.474(17) ? Cl1B O2B . 1.476(16) ? Cl1C O1C . 1.399(15) ? Cl1C O4C . 1.4357(14) ? Cl1C O3C . 1.467(11) ? Cl1C O2C . 1.484(13) ? Li1 O15 . 1.901(3) ? Li1 O5 1_655 1.910(3) ? Li1 O6 . 1.918(3) ? Li1 O16 2_657 1.946(3) ? N1 H1A . 0.85(3) ? N1 H1B . 0.90(3) ? N1 H1C . 0.83(3) ? N11 H11A . 0.91(3) ? N11 H11B . 0.88(3) ? N11 H11C . 0.86(3) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1A O6 . 0.85(3) 2.32(3) 2.872(2) 123.(3) ? N1 H1B O3 . 0.90(3) 1.99(3) 2.810(5) 151.(3) ? N1 H1B O4 1_455 0.90(3) 2.55(3) 3.024(2) 113.(2) ? N1 H1C O2 2_556 0.83(3) 2.20(3) 2.923(7) 146.(3) ? N11 H11A O16 1_455 0.91(3) 1.97(3) 2.8705(19) 169.(2) ? N11 H11B O15 2_647 0.88(3) 2.02(3) 2.892(2) 168.(3) ? N11 H11B O16 . 0.88(3) 2.51(3) 2.9986(19) 115.(2) ? N11 H11C O5 1_545 0.86(3) 1.93(3) 2.7731(19) 167.(3) ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O6 C1 C2 C3 . . . . -7.7(2) ? O5 C1 C2 C3 . . . . 171.83(14) ? C1 C2 C3 N1 . . . . -61.58(18) ? O15 C11 C12 C13 . . . . 167.18(14) ? O16 C11 C12 C13 . . . . -13.1(2) ? C11 C12 C13 N11 . . . . 71.44(18) ? O6 C1 O5 Li1 . . . 1_455 -166.69(16) ? C2 C1 O5 Li1 . . . 1_455 13.8(2) ? O5 C1 O6 Li1 . . . . 54.2(2) ? C2 C1 O6 Li1 . . . . -126.27(17) ? O16 C11 O15 Li1 . . . . -144.9(2) ? C12 C11 O15 Li1 . . . . 34.8(3) ? O15 C11 O16 Li1 . . . 2_647 83.0(2) ? C12 C11 O16 Li1 . . . 2_647 -96.7(2) ?