#------------------------------------------------------------------------------ #$Date: 2020-05-22 04:35:48 +0300 (Fri, 22 May 2020) $ #$Revision: 252267 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240565.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_7240565 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_formula_moiety 'C3 H7 Cl Li N O6' _chemical_formula_sum 'C3 H7 Cl Li N O6' _chemical_formula_weight 195.49 _chemical_name_systematic 'catena-(/m-3-beta-Alanine-lithium perchlorate)' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2019-06-17 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2020-04-04 deposited with the CCDC. 2020-05-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 125.825(3) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 24.143(3) _cell_length_b 5.0111(7) _cell_length_c 14.528(2) _cell_measurement_reflns_used 9880 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 30.56 _cell_measurement_theta_min 2.80 _cell_volume 1425.1(3) _computing_cell_refinement 'SAINT V8.38A (2016)' _computing_data_reduction 'SAINT V8.38A (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 100.01 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_unetI/netI 0.0227 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 17655 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.560 _diffrn_reflns_theta_min 2.081 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.524 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_correction_T_min 0.6833 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0901 before and 0.0649 after correction. The Ratio of minimum to maximum transmission is 0.9158. The \l/2 correction factor is Not present.' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.822 _exptl_crystal_description needle _exptl_crystal_F_000 800 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.505 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.066 _refine_ls_extinction_coef 0.0049(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 122 _refine_ls_number_reflns 2183 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.108 _refine_ls_R_factor_all 0.0306 _refine_ls_R_factor_gt 0.0276 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0293P)^2^+2.0958P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0706 _refine_ls_wR_factor_ref 0.0727 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2024 _reflns_number_total 2183 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00592d2.cif _cod_data_source_block 1 _cod_database_code 7240565 _shelx_shelxl_version_number 2018/3 _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 0.935 _shelx_estimated_absorpt_t_min 0.859 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H,H) groups 2. Restrained distances N1-H1C = N1-H1A = N1-H1B 0.9 with sigma of 0.001 3.a Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C3(H3A,H3B) ; _shelx_res_file ; TITL phm_swinia_out_100K_0m_a.res in C2/c phm_swinia_out_100k_0m_a.res created by SHELXL-2018/3 at 11:29:12 on 17-Jun-2019 REM Old TITL phm_swinia_out_100K_0m in C2/c REM SHELXT solution in C2/c REM R1 0.060, Rweak 0.001, Alpha 0.026, Orientation as input REM Formula found by SHELXT: C3 Cl Li N O2 CELL 0.71073 24.1427 5.0111 14.5282 90 125.825 90 ZERR 8 0.0031 0.0007 0.002 0 0.003 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H Cl Li N O UNIT 24 56 8 8 8 48 DFIX 0.9 0.001 N1 H1c N1 H1a N1 H1b L.S. 10 PLAN 2 SIZE 0.13 0.15 0.3 TEMP -173.14 BOND $H LIST 6 fmap 2 acta REM REM REM WGHT 0.029300 2.095800 EXTI 0.004877 FVAR 0.46990 C1 1 0.800513 0.214671 0.425667 11.00000 0.00586 0.00716 = 0.00741 -0.00047 0.00334 -0.00022 C2 1 0.830728 0.344132 0.540494 11.00000 0.01144 0.00972 = 0.00758 -0.00139 0.00581 -0.00173 AFIX 23 H2A 2 0.827430 0.217883 0.589511 11.00000 -1.20000 H2B 2 0.803666 0.504628 0.529962 11.00000 -1.20000 AFIX 0 C3 1 0.905404 0.424302 0.599771 11.00000 0.01062 0.00931 = 0.00753 -0.00007 0.00382 -0.00051 AFIX 23 H3A 2 0.923248 0.501819 0.675011 11.00000 -1.20000 H3B 2 0.932845 0.263860 0.611832 11.00000 -1.20000 AFIX 0 CL1 3 0.588893 0.550991 0.179318 11.00000 0.00824 0.00794 = 0.00760 0.00054 0.00472 0.00033 LI1 4 0.741085 0.720804 0.298380 11.00000 0.01329 0.00967 = 0.00995 0.00102 0.00590 0.00123 N1 5 0.912541 0.623473 0.530669 11.00000 0.00901 0.00904 = 0.01171 0.00016 0.00536 -0.00083 H1A 2 0.906985 0.540995 0.470751 11.00000 0.01556 H1B 2 0.953089 0.707714 0.572924 11.00000 0.02198 H1C 2 0.878966 0.745568 0.502142 11.00000 0.02187 O6 6 0.779018 0.366069 0.341558 11.00000 0.01077 0.00765 = 0.00757 0.00136 0.00486 0.00127 O5 6 0.799510 -0.036166 0.420091 11.00000 0.01066 0.00576 = 0.01017 -0.00003 0.00435 -0.00012 O1 6 0.650683 0.677838 0.272707 11.00000 0.00791 0.01668 = 0.00956 -0.00243 0.00340 -0.00215 O4 6 0.568222 0.670575 0.073259 11.00000 0.01609 0.01602 = 0.00862 0.00345 0.00601 -0.00246 O3 6 0.536057 0.591446 0.196273 11.00000 0.00946 0.01957 = 0.01515 -0.00104 0.00879 -0.00003 O2 6 0.600385 0.270837 0.178121 11.00000 0.02562 0.00824 = 0.01686 0.00006 0.01272 0.00320 HKLF 4 REM phm_swinia_out_100K_0m_a.res in C2/c REM wR2 = 0.0727, GooF = S = 1.109, Restrained GooF = 1.108 for all data REM R1 = 0.0276 for 2024 Fo > 4sig(Fo) and 0.0306 for all 2183 data REM 122 parameters refined using 3 restraints END WGHT 0.0293 2.0958 REM Highest difference peak 0.505, deepest hole -0.469, 1-sigma level 0.066 Q1 1 0.5936 0.4024 0.1814 11.00000 0.05 0.51 Q2 1 0.8687 0.3874 0.5682 11.00000 0.05 0.47 ; _shelx_res_checksum 58140 _olex2_submission_special_instructions 'No special instructions were received' 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' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' 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 C1 C 0.80051(5) 0.2147(2) 0.42567(9) 0.00713(19) Uani 1 1 d . . . . . C2 C 0.83073(6) 0.3441(2) 0.54049(9) 0.0094(2) Uani 1 1 d . . . . . H2A H 0.827430 0.217883 0.589511 0.011 Uiso 1 1 calc R . . . . H2B H 0.803666 0.504628 0.529962 0.011 Uiso 1 1 calc R . . . . C3 C 0.90540(6) 0.4243(2) 0.59977(10) 0.0100(2) Uani 1 1 d . . . . . H3A H 0.923248 0.501819 0.675011 0.012 Uiso 1 1 calc R . . . . H3B H 0.932845 0.263860 0.611832 0.012 Uiso 1 1 calc R . . . . Cl1 Cl 0.58889(2) 0.55099(5) 0.17932(2) 0.00787(9) Uani 1 1 d . . . . . Li1 Li 0.74108(11) 0.7208(4) 0.29838(18) 0.0115(4) Uani 1 1 d . . . . . N1 N 0.91254(5) 0.6235(2) 0.53067(9) 0.01034(19) Uani 1 1 d D . . . . H1A H 0.9070(9) 0.541(3) 0.4708(9) 0.016(4) Uiso 1 1 d D . . . . H1B H 0.9531(5) 0.708(3) 0.5729(13) 0.022(5) Uiso 1 1 d D . . . . H1C H 0.8790(6) 0.746(3) 0.5021(15) 0.022(5) Uiso 1 1 d D . . . . O6 O 0.77902(4) 0.36607(17) 0.34156(7) 0.00896(16) Uani 1 1 d . . . . . O5 O 0.79951(4) -0.03617(17) 0.42009(7) 0.00990(17) Uani 1 1 d . . . . . O1 O 0.65068(4) 0.67784(18) 0.27271(7) 0.01240(18) Uani 1 1 d . . . . . O4 O 0.56822(5) 0.67057(19) 0.07326(7) 0.01430(19) Uani 1 1 d . . . . . O3 O 0.53606(5) 0.59145(19) 0.19627(8) 0.01378(18) Uani 1 1 d . . . . . O2 O 0.60039(5) 0.27084(19) 0.17812(8) 0.0167(2) Uani 1 1 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 C1 0.0059(4) 0.0072(5) 0.0074(4) -0.0005(3) 0.0033(4) -0.0002(3) C2 0.0114(5) 0.0097(5) 0.0076(4) -0.0014(4) 0.0058(4) -0.0017(4) C3 0.0106(5) 0.0093(5) 0.0075(5) -0.0001(4) 0.0038(4) -0.0005(4) Cl1 0.00824(13) 0.00794(13) 0.00760(13) 0.00054(8) 0.00472(10) 0.00033(8) Li1 0.0133(9) 0.0097(9) 0.0099(9) 0.0010(7) 0.0059(8) 0.0012(7) N1 0.0090(4) 0.0090(4) 0.0117(4) 0.0002(3) 0.0054(4) -0.0008(3) O6 0.0108(4) 0.0077(4) 0.0076(3) 0.0014(3) 0.0049(3) 0.0013(3) O5 0.0107(4) 0.0058(4) 0.0102(4) 0.0000(3) 0.0043(3) -0.0001(3) O1 0.0079(4) 0.0167(4) 0.0096(4) -0.0024(3) 0.0034(3) -0.0022(3) O4 0.0161(4) 0.0160(4) 0.0086(4) 0.0035(3) 0.0060(3) -0.0025(3) O3 0.0095(4) 0.0196(4) 0.0151(4) -0.0010(3) 0.0088(3) 0.0000(3) O2 0.0256(5) 0.0082(4) 0.0169(4) 0.0001(3) 0.0127(4) 0.0032(3) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 Li1 152.83(9) . 4_645 ? O6 C1 C2 117.82(10) . . ? O6 C1 Li1 36.96(7) . 4_645 ? O5 C1 C2 118.39(10) . . ? O5 C1 Li1 87.46(8) . 4_645 ? O5 C1 O6 123.77(10) . . ? C1 C2 H2A 109.1 . . ? C1 C2 H2B 109.1 . . ? C1 C2 C3 112.37(9) . . ? H2A C2 H2B 107.9 . . ? C3 C2 H2A 109.1 . . ? C3 C2 H2B 109.1 . . ? C2 C3 H3A 109.4 . . ? C2 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? N1 C3 C2 111.01(9) . . ? N1 C3 H3A 109.4 . . ? N1 C3 H3B 109.4 . . ? O4 Cl1 O1 109.91(5) . . ? O4 Cl1 O3 109.57(6) . . ? O3 Cl1 O1 107.81(5) . . ? O2 Cl1 O1 109.90(6) . . ? O2 Cl1 O4 110.01(6) . . ? O2 Cl1 O3 109.59(6) . . ? C1 Li1 Li1 61.23(8) 4_655 4_655 ? C1 Li1 Li1 60.03(8) 4_655 4_645 ? Li1 Li1 Li1 111.87(13) 4_645 4_655 ? O6 Li1 C1 98.48(9) . 4_655 ? O6 Li1 C1 23.11(4) 4_655 4_655 ? O6 Li1 Li1 80.78(11) 4_655 4_645 ? O6 Li1 Li1 38.55(3) . 4_645 ? O6 Li1 Li1 38.41(8) 4_655 4_655 ? O6 Li1 Li1 138.16(14) . 4_655 ? O6 Li1 O6 117.90(11) . 4_655 ? O6 Li1 O1 102.72(11) . . ? O6 Li1 O1 105.63(10) 4_655 . ? O5 Li1 C1 130.62(11) 1_565 4_655 ? O5 Li1 Li1 71.01(7) 1_565 4_655 ? O5 Li1 Li1 136.59(14) 1_565 4_645 ? O5 Li1 O6 109.41(11) 1_565 . ? O5 Li1 O6 109.06(11) 1_565 4_655 ? O5 Li1 O1 111.95(11) 1_565 . ? O1 Li1 C1 99.97(9) . 4_655 ? O1 Li1 Li1 116.06(11) . 4_655 ? O1 Li1 Li1 105.12(10) . 4_645 ? C3 N1 H1A 109.4(11) . . ? C3 N1 H1B 111.2(12) . . ? C3 N1 H1C 109.6(12) . . ? H1A N1 H1B 111.2(16) . . ? H1A N1 H1C 106.4(16) . . ? H1B N1 H1C 108.8(17) . . ? C1 O6 Li1 135.74(10) . . ? C1 O6 Li1 119.92(10) . 4_645 ? Li1 O6 Li1 103.04(7) . 4_645 ? C1 O5 Li1 132.01(10) . 1_545 ? Cl1 O1 Li1 129.42(8) . . ? 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 C1 C2 1.5203(15) . ? C1 Li1 2.789(2) 4_645 ? C1 O6 1.2632(13) . ? C1 O5 1.2589(14) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.5284(16) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C3 N1 1.4954(15) . ? Cl1 O1 1.4495(9) . ? Cl1 O4 1.4430(9) . ? Cl1 O3 1.4480(9) . ? Cl1 O2 1.4331(10) . ? Li1 Li1 3.024(2) 4_645 ? Li1 Li1 3.024(2) 4_655 ? Li1 O6 1.935(2) 4_655 ? Li1 O6 1.929(2) . ? Li1 O5 1.918(2) 1_565 ? Li1 O1 1.999(2) . ? N1 H1A 0.8999(10) . ? N1 H1B 0.8999(11) . ? N1 H1C 0.8999(10) . ?