#------------------------------------------------------------------------------ #$Date: 2024-07-05 17:11:19 +0300 (Fri, 05 Jul 2024) $ #$Revision: 292876 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/17/1571721.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_1571721 loop_ _publ_author_name 'Li, Yang' 'Ok, Kang Min' _publ_section_title ; Crystal clear: unveiling giant birefringence in organic--inorganic cocrystals ; _journal_issue 26 _journal_name_full 'Chemical Science' _journal_page_first 10193 _journal_page_last 10199 _journal_paper_doi 10.1039/D4SC02569E _journal_volume 15 _journal_year 2024 _chemical_formula_moiety 'C10 H14 Li2 N4 O10' _chemical_formula_sum 'C10 H14 Li2 N4 O10' _chemical_formula_weight 364.13 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 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 90 _cell_angle_beta 110.89(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 8.821(8) _cell_length_b 10.477(9) _cell_length_c 9.205(9) _cell_measurement_reflns_used 2793 _cell_measurement_temperature 171.00 _cell_measurement_theta_max 27.049 _cell_measurement_theta_min 3.064 _cell_volume 794.8(13) _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 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 171.00 _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'PHOTON II CPAD detector' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker D8 QUEST' _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1264 _diffrn_reflns_av_unetI/netI 0.0732 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 14271 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.483 _diffrn_reflns_theta_min 2.747 _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.4475 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1416 before and 0.1095 after correction. The Ratio of minimum to maximum transmission is 0.6001. 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 1.522 _exptl_crystal_description block _exptl_crystal_F_000 376 _exptl_crystal_size_max 0.216 _exptl_crystal_size_mid 0.126 _exptl_crystal_size_min 0.098 _refine_diff_density_max 0.245 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.056 _refine_ls_extinction_coef 0.028(5) _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 1.019 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 122 _refine_ls_number_reflns 1823 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.022 _refine_ls_R_factor_all 0.0926 _refine_ls_R_factor_gt 0.0535 _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^)+(0.0451P)^2^+0.3964P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1130 _refine_ls_wR_factor_ref 0.1307 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1235 _reflns_number_total 1823 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc02569e2.cif _cod_data_source_block 1 _cod_depositor_comments 'Adding full bibliography for 1571720--1571722.cif.' _cod_database_code 1571721 _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 0.987 _shelx_estimated_absorpt_t_min 0.972 _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-H2A \\sim Li1-H2B with sigma of 0.02 3.a Free rotating group: O2(H2A,H2B) 3.b Aromatic/amide H refined with riding coordinates: N1(H1), C5(H5), C4(H4), C2(H2), C3(H3) ; _shelx_res_file ; TITL 1_a.res in P2(1)/n 1.res created by SHELXL-2018/3 at 09:28:49 on 08-Apr-2024 REM Old TITL 1 in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.134, Rweak 0.016, Alpha 0.027 REM 0.450 for 98 systematic absences, Orientation as input REM Formula found by SHELXT: C5 Li N2 O5 CELL 0.71073 8.8206 10.4769 9.2052 90 110.886 90 ZERR 2 0.0082 0.009 0.0086 0 0.034 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H Li N O UNIT 20 28 4 8 20 EQIV $1 1.5-X,0.5+Y,1.5-Z EQIV $2 1-X,1-Y,1-Z EQIV $3 1-X,1-Y,-Z SADI Li1 H2a Li1 H2b L.S. 50 PLAN 5 SIZE 0.216 0.126 0.098 TEMP -102.15 CONF HTAB O2 O5_$1 HTAB O2 O5_$2 HTAB N1 O4_$3 BOND list 4 MORE -1 BOND $H fmap 2 acta OMIT 2 10 5 REM REM REM WGHT 0.045100 0.396400 EXTI 0.028010 FVAR 0.96415 O1 5 0.904771 0.538138 0.357220 11.00000 0.02404 0.04425 = 0.01796 0.00209 0.00698 0.00266 O3 5 0.760321 0.374487 0.634695 11.00000 0.02689 0.03626 = 0.02497 -0.00410 0.00371 0.00110 AFIX 6 O2 5 0.802430 0.671508 0.630661 11.00000 0.03261 0.03521 = 0.03167 -0.00879 0.01046 0.00228 H2A 2 0.702690 0.698658 0.594021 11.00000 -1.50000 H2B 2 0.842520 0.704810 0.723140 11.00000 -1.50000 AFIX 0 O5 5 0.527998 0.279133 0.549549 11.00000 0.03292 0.03179 = 0.05060 0.00916 0.01668 -0.00453 O4 5 0.590872 0.421744 0.407700 11.00000 0.05388 0.03949 = 0.02179 0.00959 0.01363 0.00290 N2 4 0.625029 0.358393 0.529482 11.00000 0.02798 0.02281 = 0.02223 0.00029 0.01073 0.00267 N1 4 0.609707 0.603870 -0.087293 11.00000 0.03688 0.03526 = 0.01924 0.00725 0.00360 -0.00425 AFIX 43 H1 2 0.545061 0.617246 -0.183928 11.00000 -1.20000 AFIX 0 C1 1 0.812172 0.559554 0.217523 11.00000 0.02144 0.02751 = 0.02004 0.00073 0.00950 -0.00258 C5 1 0.830939 0.494466 0.089018 11.00000 0.03491 0.02867 = 0.02720 -0.00137 0.01479 0.00568 AFIX 43 H5 2 0.915296 0.433391 0.107101 11.00000 -1.20000 AFIX 0 C4 1 0.730927 0.518215 -0.057642 11.00000 0.05160 0.03236 = 0.02117 -0.00363 0.01686 -0.00280 AFIX 43 H4 2 0.746085 0.473894 -0.141469 11.00000 -1.20000 AFIX 0 C2 1 0.681982 0.649081 0.178355 11.00000 0.03093 0.03224 = 0.02520 -0.00221 0.01149 0.00442 AFIX 43 H2 2 0.662346 0.695282 0.258691 11.00000 -1.20000 AFIX 0 C3 1 0.585974 0.669257 0.028543 11.00000 0.03413 0.03142 = 0.03579 0.00704 0.01341 0.00493 AFIX 43 H3 2 0.500896 0.730254 0.004921 11.00000 -1.20000 AFIX 0 LI1 3 0.870414 0.516980 0.552603 11.00000 0.03094 0.03274 = 0.02453 -0.00101 0.01352 0.00165 HKLF 4 REM 1_a.res in P2(1)/n REM wR2 = 0.1307, GooF = S = 1.019, Restrained GooF = 1.022 for all data REM R1 = 0.0535 for 1235 Fo > 4sig(Fo) and 0.0926 for all 1823 data REM 122 parameters refined using 1 restraints END WGHT 0.0451 0.3965 REM Highest difference peak 0.245, deepest hole -0.225, 1-sigma level 0.056 Q1 1 0.7720 0.6254 0.1962 11.00000 0.05 0.24 Q2 1 0.7077 0.5746 0.1950 11.00000 0.05 0.22 Q3 1 0.7983 0.4945 0.1517 11.00000 0.05 0.21 Q4 1 1.0109 0.5048 0.3390 11.00000 0.05 0.20 Q5 1 0.6153 0.3617 0.4339 11.00000 0.05 0.19 ; _shelx_res_checksum 2977 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -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 O1 O 0.90477(19) 0.53814(16) 0.35722(17) 0.0289(4) Uani 1 1 d . . . . . O3 O 0.76032(19) 0.37449(15) 0.63469(18) 0.0309(4) Uani 1 1 d . . . . . O2 O 0.8024(2) 0.67151(16) 0.63066(19) 0.0334(5) Uani 1 1 d G . . . . H2A H 0.702690 0.698658 0.594021 0.050 Uiso 1 1 d DG U . . . H2B H 0.842520 0.704810 0.723140 0.050 Uiso 1 1 d DG U . . . O5 O 0.5280(2) 0.27913(16) 0.5495(2) 0.0380(5) Uani 1 1 d . . . . . O4 O 0.5909(2) 0.42174(16) 0.40770(19) 0.0383(5) Uani 1 1 d . . . . . N2 N 0.6250(2) 0.35839(17) 0.5295(2) 0.0239(4) Uani 1 1 d . . . . . N1 N 0.6097(3) 0.60387(19) -0.0873(2) 0.0322(5) Uani 1 1 d . . . . . H1 H 0.545061 0.617246 -0.183928 0.039 Uiso 1 1 calc R U . . . C1 C 0.8122(3) 0.5596(2) 0.2175(2) 0.0224(5) Uani 1 1 d . . . . . C5 C 0.8309(3) 0.4945(2) 0.0890(3) 0.0292(6) Uani 1 1 d . . . . . H5 H 0.915296 0.433391 0.107101 0.035 Uiso 1 1 calc R U . . . C4 C 0.7309(3) 0.5182(2) -0.0576(3) 0.0340(6) Uani 1 1 d . . . . . H4 H 0.746085 0.473894 -0.141469 0.041 Uiso 1 1 calc R U . . . C2 C 0.6820(3) 0.6491(2) 0.1784(3) 0.0291(6) Uani 1 1 d . . . . . H2 H 0.662346 0.695282 0.258691 0.035 Uiso 1 1 calc R U . . . C3 C 0.5860(3) 0.6693(2) 0.0285(3) 0.0335(6) Uani 1 1 d . . . . . H3 H 0.500896 0.730254 0.004921 0.040 Uiso 1 1 calc R U . . . Li1 Li 0.8704(5) 0.5170(4) 0.5526(4) 0.0284(9) 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 O1 0.0240(9) 0.0443(10) 0.0180(8) 0.0021(7) 0.0070(7) 0.0027(7) O3 0.0269(9) 0.0363(10) 0.0250(9) -0.0041(7) 0.0037(7) 0.0011(7) O2 0.0326(10) 0.0352(10) 0.0317(10) -0.0088(7) 0.0105(8) 0.0023(8) O5 0.0329(10) 0.0318(9) 0.0506(12) 0.0092(8) 0.0167(9) -0.0045(8) O4 0.0539(12) 0.0395(10) 0.0218(9) 0.0096(7) 0.0136(8) 0.0029(9) N2 0.0280(11) 0.0228(9) 0.0222(10) 0.0003(8) 0.0107(8) 0.0027(8) N1 0.0369(12) 0.0353(11) 0.0192(10) 0.0073(8) 0.0036(8) -0.0042(9) C1 0.0214(12) 0.0275(11) 0.0200(11) 0.0007(9) 0.0095(9) -0.0026(9) C5 0.0349(14) 0.0287(12) 0.0272(12) -0.0014(9) 0.0148(11) 0.0057(10) C4 0.0516(17) 0.0324(13) 0.0212(12) -0.0036(10) 0.0169(12) -0.0028(12) C2 0.0309(13) 0.0322(12) 0.0252(12) -0.0022(10) 0.0115(10) 0.0044(10) C3 0.0341(14) 0.0314(13) 0.0358(14) 0.0070(11) 0.0134(12) 0.0049(11) Li1 0.031(2) 0.033(2) 0.025(2) -0.0010(16) 0.0135(17) 0.0016(16) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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_ _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 C1 O1 Li1 134.44(19) . . ? C1 O1 Li1 132.27(18) . 3_766 ? Li1 O1 Li1 92.46(18) . 3_766 ? N2 O3 Li1 104.90(17) . . ? H2A O2 H2B 104.5 . . ? Li1 O2 H2A 122.0 . . ? Li1 O2 H2B 128.5 . . ? N2 O4 Li1 81.90(16) . . ? O3 N2 O5 119.23(19) . . ? O3 N2 Li1 48.23(13) . . ? O5 N2 Li1 167.33(17) . . ? O4 N2 O3 118.90(19) . . ? O4 N2 O5 121.9(2) . . ? O4 N2 Li1 70.70(15) . . ? C4 N1 H1 119.5 . . ? C3 N1 H1 119.5 . . ? C3 N1 C4 121.0(2) . . ? O1 C1 C5 122.1(2) . . ? O1 C1 C2 122.7(2) . . ? C5 C1 C2 115.2(2) . . ? C1 C5 H5 119.5 . . ? C4 C5 C1 121.0(2) . . ? C4 C5 H5 119.5 . . ? N1 C4 H4 119.5 . . ? C5 C4 N1 121.0(2) . . ? C5 C4 H4 119.5 . . ? C1 C2 H2 119.5 . . ? C3 C2 C1 121.0(2) . . ? C3 C2 H2 119.5 . . ? N1 C3 C2 120.7(2) . . ? N1 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? O1 Li1 O1 87.54(18) . 3_766 ? O1 Li1 O3 99.79(19) 3_766 . ? O1 Li1 O3 132.1(2) . . ? O1 Li1 O2 119.3(2) 3_766 . ? O1 Li1 O2 114.6(2) . . ? O1 Li1 O4 139.1(2) 3_766 . ? O1 Li1 O4 90.07(16) . . ? O1 Li1 N2 112.73(18) . . ? O1 Li1 N2 121.49(19) 3_766 . ? O1 Li1 Li1 43.71(13) 3_766 3_766 ? O1 Li1 Li1 43.83(12) . 3_766 ? O3 Li1 O4 54.25(12) . . ? O3 Li1 N2 26.87(8) . . ? O3 Li1 Li1 125.6(2) . 3_766 ? O2 Li1 O3 102.64(19) . . ? O2 Li1 O4 98.65(18) . . ? O2 Li1 N2 101.45(18) . . ? O2 Li1 Li1 128.9(3) . 3_766 ? O4 Li1 N2 27.40(7) . . ? O4 Li1 Li1 121.6(2) . 3_766 ? N2 Li1 Li1 129.0(2) . 3_766 ? 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 O1 C1 1.274(3) . ? O1 Li1 1.945(5) 3_766 ? O1 Li1 1.940(4) . ? O3 N2 1.252(3) . ? O3 Li1 2.065(4) . ? O2 H2A 0.8701 . ? O2 H2B 0.8700 . ? O2 Li1 1.950(4) . ? O5 N2 1.253(3) . ? O4 N2 1.244(2) . ? O4 Li1 2.551(5) . ? N2 Li1 2.676(5) . ? N1 H1 0.8800 . ? N1 C4 1.347(3) . ? N1 C3 1.345(3) . ? C1 C5 1.425(3) . ? C1 C2 1.426(3) . ? C5 H5 0.9500 . ? C5 C4 1.347(3) . ? C4 H4 0.9500 . ? C2 H2 0.9500 . ? C2 C3 1.353(3) . ? C3 H3 0.9500 . ? Li1 Li1 2.805(8) 3_766 ? 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 O2 H2A O5 0.87 2.01 2.840(3) 160.3 3_666 yes O2 H2B O5 0.87 2.14 3.006(3) 172.4 2_656 yes N1 H1 O4 0.88 2.02 2.860(4) 158.9 3_665 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 O1 C1 C5 C4 179.6(2) . . . . ? O1 C1 C2 C3 -179.9(2) . . . . ? C1 C5 C4 N1 -0.3(4) . . . . ? C1 C2 C3 N1 0.9(4) . . . . ? C5 C1 C2 C3 -0.4(3) . . . . ? C4 N1 C3 C2 -1.1(4) . . . . ? C2 C1 C5 C4 0.1(3) . . . . ? C3 N1 C4 C5 0.7(4) . . . . ? Li1 O1 C1 C5 29.1(4) 3_766 . . . ? Li1 O1 C1 C5 -137.4(3) . . . . ? Li1 O1 C1 C2 -151.4(2) 3_766 . . . ? Li1 O1 C1 C2 42.0(4) . . . . ? Li1 O3 N2 O5 -177.73(18) . . . . ? Li1 O3 N2 O4 2.3(2) . . . . ? Li1 O4 N2 O3 -1.82(19) . . . . ? Li1 O4 N2 O5 178.2(2) . . . . ?