#------------------------------------------------------------------------------ #$Date: 2024-04-19 05:33:21 +0300 (Fri, 19 Apr 2024) $ #$Revision: 291282 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/31/7063177.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_7063177 loop_ _publ_author_name 'Lepcha, Gerald' 'Pal, Indrajit' 'Majumdar, Santanu' 'Dhasmana, Yogesh' 'Mondal, Sanjay' 'Zangrando, Ennio' 'Chopra, Deepak' 'Dey, Biswajit' _publ_section_title ; Solvent and Stoichiometry-dependent Versatile Organogelation and Robust Crystallization from Supramolecular Association of Adipic Acid and Triethanolamine ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D4NJ00559G _journal_year 2024 _chemical_formula_moiety 'C6 H8 O4, 2(C6 H16 N O3)' _chemical_formula_sum 'C18 H40 N2 O10' _chemical_formula_weight 444.52 _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 2023-11-17 _audit_creation_method ; Olex2 1.5 (compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817) ; _audit_update_record ; 2023-11-19 deposited with the CCDC. 2024-04-18 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 95.4020(10) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 5.3882(2) _cell_length_b 14.1701(4) _cell_length_c 14.4214(4) _cell_measurement_reflns_used 9942 _cell_measurement_temperature 100.00 _cell_measurement_theta_max 79.81 _cell_measurement_theta_min 4.38 _cell_volume 1096.20(6) _computing_cell_refinement 'SAINT V8.40A (Bruker, 2019)' _computing_data_reduction 'SAINT V8.40A (Bruker, 2019)' _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 'olex2.solve 1.5 (Bourhis et al., 2015)' _diffrn_ambient_temperature 100.00 _diffrn_measured_fraction_theta_full 0.973 _diffrn_measured_fraction_theta_max 0.974 _diffrn_measurement_device_type 'D8 Venture' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0641 _diffrn_reflns_av_unetI/netI 0.0263 _diffrn_reflns_Laue_measured_fraction_full 0.973 _diffrn_reflns_Laue_measured_fraction_max 0.974 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 30140 _diffrn_reflns_point_group_measured_fraction_full 0.973 _diffrn_reflns_point_group_measured_fraction_max 0.974 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 79.941 _diffrn_reflns_theta_min 4.384 _exptl_absorpt_coefficient_mu 0.918 _exptl_absorpt_correction_T_max 0.5179 _exptl_absorpt_correction_T_min 0.3161 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1147 before and 0.0696 after correction. The Ratio of minimum to maximum transmission is 0.6103. 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 1.347 _exptl_crystal_description plate _exptl_crystal_F_000 484 _exptl_crystal_size_max 0.066 _exptl_crystal_size_mid 0.053 _exptl_crystal_size_min 0.051 _refine_diff_density_max 0.262 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.036 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 152 _refine_ls_number_reflns 2322 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.020 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0338 _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^)+(0.0330P)^2^+0.4106P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0764 _refine_ls_wR_factor_ref 0.0787 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2079 _reflns_number_total 2322 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4nj00559g2.cif _cod_data_source_block dmso _cod_database_code 7063177 _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 0.955 _shelx_estimated_absorpt_t_min 0.942 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H,H) groups 2.a Secondary CH2 refined with riding coordinates: C5(H5A,H5B), C4(H4A,H4B), C2(H2A,H2B), C3(H3A,H3B), C9(H9A,H9B), C8(H8A,H8B), C6(H6A,H6B), C7(H7A,H7B) ; _shelx_res_file ; TITL dmso.res in P2(1)/n dmso.res created by SHELXL-2018/3 at 11:24:34 on 17-Nov-2023 REM Old TITL MONO in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.104, Rweak 0.009, Alpha 0.026, Orientation as input REM Formula found by SHELXT: C9 N O5 CELL 1.54178 5.3882 14.1701 14.4214 90 95.402 90 ZERR 2 0.0002 0.0004 0.0004 0 0.001 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O UNIT 36 80 4 20 L.S. 10 PLAN 1 SIZE 0.051 0.053 0.066 TEMP -173.15 CONF LIST 4 MORE -1 BOND $H fmap 2 acta SHEL 999 0.78 REM REM REM WGHT 0.033000 0.410600 FVAR 1.42472 O3 4 0.441852 0.515373 0.629504 11.00000 0.01746 0.02231 = 0.02185 -0.00306 0.00139 0.00166 O5 4 0.504343 0.299680 0.774242 11.00000 0.02155 0.01936 = 0.02595 0.00055 0.00410 -0.00207 O2 4 0.221256 0.627105 0.741891 11.00000 0.02252 0.02238 = 0.02134 0.00061 0.00315 0.00479 O1 4 0.005261 0.618936 0.865286 11.00000 0.01748 0.02616 = 0.02528 -0.00019 0.00366 0.00249 O4 4 0.481464 0.263825 0.517468 11.00000 0.02214 0.02509 = 0.02235 0.00061 -0.00076 -0.00107 N1 3 0.794367 0.370927 0.640898 11.00000 0.01373 0.01533 = 0.01646 0.00131 0.00073 0.00012 C5 1 0.695354 0.543292 0.631358 11.00000 0.01929 0.01669 = 0.02133 0.00131 -0.00040 -0.00069 AFIX 23 H5A 2 0.763230 0.557728 0.695986 11.00000 -1.20000 H5B 2 0.709956 0.600520 0.592868 11.00000 -1.20000 AFIX 0 C4 1 0.837847 0.462749 0.593129 11.00000 0.01823 0.01709 = 0.02025 0.00370 0.00305 -0.00168 AFIX 23 H4A 2 0.786882 0.456092 0.525683 11.00000 -1.20000 H4B 2 1.018176 0.477565 0.600658 11.00000 -1.20000 AFIX 0 C1 1 0.192405 0.598585 0.823933 11.00000 0.01669 0.01542 = 0.02109 -0.00386 0.00028 -0.00239 C2 1 0.396680 0.537027 0.872378 11.00000 0.01647 0.01849 = 0.02169 -0.00127 0.00133 0.00015 AFIX 23 H2A 2 0.560324 0.564476 0.861402 11.00000 -1.20000 H2B 2 0.386898 0.473678 0.843313 11.00000 -1.20000 AFIX 0 C3 1 0.385671 0.525676 0.977010 11.00000 0.01719 0.02132 = 0.02176 0.00033 0.00181 0.00103 AFIX 23 H3A 2 0.233789 0.489850 0.988452 11.00000 -1.20000 H3B 2 0.374016 0.588780 1.005742 11.00000 -1.20000 AFIX 0 C9 1 0.767316 0.291207 0.792562 11.00000 0.02310 0.02190 = 0.01874 0.00384 -0.00056 0.00001 AFIX 23 H9A 2 0.823251 0.229436 0.770120 11.00000 -1.20000 H9B 2 0.815491 0.295317 0.860401 11.00000 -1.20000 AFIX 0 C8 1 0.888149 0.370614 0.742470 11.00000 0.01939 0.02077 = 0.01732 0.00121 -0.00289 -0.00121 AFIX 23 H8A 2 0.849191 0.431814 0.770874 11.00000 -1.20000 H8B 2 1.071423 0.362402 0.749135 11.00000 -1.20000 AFIX 0 C6 1 0.898869 0.290276 0.588889 11.00000 0.01899 0.01794 = 0.02403 -0.00074 0.00427 0.00358 AFIX 23 H6A 2 0.908731 0.233163 0.628606 11.00000 -1.20000 H6B 2 1.069601 0.306134 0.573999 11.00000 -1.20000 AFIX 0 C7 1 0.735186 0.270318 0.499349 11.00000 0.02582 0.01985 = 0.01949 -0.00163 0.00600 0.00078 AFIX 23 H7A 2 0.755019 0.321546 0.453954 11.00000 -1.20000 H7B 2 0.787747 0.210389 0.471822 11.00000 -1.20000 AFIX 0 H1 2 0.624225 0.363480 0.638696 11.00000 0.02382 H5 2 0.439907 0.241079 0.770048 11.00000 0.04504 H4 2 0.470757 0.212891 0.552184 11.00000 0.04625 H3 2 0.372065 0.549884 0.667299 11.00000 0.04492 HKLF 4 REM dmso.res in P2(1)/n REM wR2 = 0.0787, GooF = S = 1.020, Restrained GooF = 1.020 for all data REM R1 = 0.0338 for 2079 Fo > 4sig(Fo) and 0.0389 for all 2322 data REM 152 parameters refined using 0 restraints END WGHT 0.0352 0.3519 REM Highest difference peak 0.262, deepest hole -0.168, 1-sigma level 0.036 Q1 1 0.2846 0.5638 0.8460 11.00000 0.05 0.26 ; _shelx_res_checksum 64295 _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 O3 O 0.44185(14) 0.51537(6) 0.62950(5) 0.02057(18) Uani 1 1 d . . . . . O5 O 0.50434(15) 0.29968(6) 0.77424(6) 0.02217(19) Uani 1 1 d . . . . . O2 O 0.22126(14) 0.62711(5) 0.74189(5) 0.02201(19) Uani 1 1 d . . . . . O1 O 0.00526(14) 0.61894(6) 0.86529(6) 0.02287(19) Uani 1 1 d . . . . . O4 O 0.48146(15) 0.26382(6) 0.51747(6) 0.02337(19) Uani 1 1 d . . . . . N1 N 0.79437(16) 0.37093(6) 0.64090(6) 0.01522(19) Uani 1 1 d . . . . . C5 C 0.6954(2) 0.54329(8) 0.63136(8) 0.0193(2) Uani 1 1 d . . . . . H5A H 0.763230 0.557728 0.695986 0.023 Uiso 1 1 calc R U . . . H5B H 0.709956 0.600520 0.592868 0.023 Uiso 1 1 calc R U . . . C4 C 0.8378(2) 0.46275(7) 0.59313(7) 0.0184(2) Uani 1 1 d . . . . . H4A H 0.786882 0.456092 0.525683 0.022 Uiso 1 1 calc R U . . . H4B H 1.018176 0.477565 0.600658 0.022 Uiso 1 1 calc R U . . . C1 C 0.19241(19) 0.59859(7) 0.82393(7) 0.0178(2) Uani 1 1 d . . . . . C2 C 0.39668(19) 0.53703(8) 0.87238(7) 0.0189(2) Uani 1 1 d . . . . . H2A H 0.560324 0.564476 0.861402 0.023 Uiso 1 1 calc R U . . . H2B H 0.386898 0.473678 0.843313 0.023 Uiso 1 1 calc R U . . . C3 C 0.38567(19) 0.52568(8) 0.97701(7) 0.0201(2) Uani 1 1 d . . . . . H3A H 0.233789 0.489850 0.988452 0.024 Uiso 1 1 calc R U . . . H3B H 0.374016 0.588780 1.005742 0.024 Uiso 1 1 calc R U . . . C9 C 0.7673(2) 0.29121(8) 0.79256(8) 0.0214(2) Uani 1 1 d . . . . . H9A H 0.823251 0.229436 0.770120 0.026 Uiso 1 1 calc R U . . . H9B H 0.815491 0.295317 0.860401 0.026 Uiso 1 1 calc R U . . . C8 C 0.8881(2) 0.37061(8) 0.74247(7) 0.0195(2) Uani 1 1 d . . . . . H8A H 0.849191 0.431814 0.770874 0.023 Uiso 1 1 calc R U . . . H8B H 1.071423 0.362402 0.749135 0.023 Uiso 1 1 calc R U . . . C6 C 0.8989(2) 0.29028(8) 0.58889(8) 0.0202(2) Uani 1 1 d . . . . . H6A H 0.908731 0.233163 0.628606 0.024 Uiso 1 1 calc R U . . . H6B H 1.069601 0.306134 0.573999 0.024 Uiso 1 1 calc R U . . . C7 C 0.7352(2) 0.27032(8) 0.49935(8) 0.0215(2) Uani 1 1 d . . . . . H7A H 0.755019 0.321546 0.453954 0.026 Uiso 1 1 calc R U . . . H7B H 0.787747 0.210389 0.471822 0.026 Uiso 1 1 calc R U . . . H1 H 0.624(3) 0.3635(10) 0.6387(9) 0.024(3) Uiso 1 1 d . . . . . H5 H 0.440(3) 0.2411(13) 0.7700(12) 0.045(5) Uiso 1 1 d . . . . . H4 H 0.471(3) 0.2129(13) 0.5522(12) 0.046(5) Uiso 1 1 d . . . . . H3 H 0.372(3) 0.5499(13) 0.6673(12) 0.045(5) Uiso 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 O3 0.0175(4) 0.0223(4) 0.0218(4) -0.0031(3) 0.0014(3) 0.0017(3) O5 0.0215(4) 0.0194(4) 0.0260(4) 0.0005(3) 0.0041(3) -0.0021(3) O2 0.0225(4) 0.0224(4) 0.0213(4) 0.0006(3) 0.0031(3) 0.0048(3) O1 0.0175(4) 0.0262(4) 0.0253(4) -0.0002(3) 0.0037(3) 0.0025(3) O4 0.0221(4) 0.0251(4) 0.0223(4) 0.0006(3) -0.0008(3) -0.0011(3) N1 0.0137(4) 0.0153(4) 0.0165(4) 0.0013(3) 0.0007(3) 0.0001(3) C5 0.0193(5) 0.0167(5) 0.0213(5) 0.0013(4) -0.0004(4) -0.0007(4) C4 0.0182(5) 0.0171(5) 0.0202(5) 0.0037(4) 0.0031(4) -0.0017(4) C1 0.0167(5) 0.0154(5) 0.0211(5) -0.0039(4) 0.0003(4) -0.0024(4) C2 0.0165(5) 0.0185(5) 0.0217(5) -0.0013(4) 0.0013(4) 0.0001(4) C3 0.0172(5) 0.0213(5) 0.0218(5) 0.0003(4) 0.0018(4) 0.0010(4) C9 0.0231(6) 0.0219(5) 0.0187(5) 0.0038(4) -0.0006(4) 0.0000(4) C8 0.0194(5) 0.0208(5) 0.0173(5) 0.0012(4) -0.0029(4) -0.0012(4) C6 0.0190(5) 0.0179(5) 0.0240(5) -0.0007(4) 0.0043(4) 0.0036(4) C7 0.0258(6) 0.0198(5) 0.0195(5) -0.0016(4) 0.0060(4) 0.0008(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' N N 0.0311 0.0180 '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' 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 C5 O3 H3 108.2(12) . . ? C9 O5 H5 107.8(11) . . ? C7 O4 H4 105.8(11) . . ? C4 N1 C8 113.39(8) . . ? C4 N1 C6 110.34(8) . . ? C4 N1 H1 106.4(9) . . ? C8 N1 C6 112.09(8) . . ? C8 N1 H1 106.0(8) . . ? C6 N1 H1 108.3(9) . . ? O3 C5 H5A 110.2 . . ? O3 C5 H5B 110.2 . . ? O3 C5 C4 107.71(9) . . ? H5A C5 H5B 108.5 . . ? C4 C5 H5A 110.2 . . ? C4 C5 H5B 110.2 . . ? N1 C4 C5 112.41(8) . . ? N1 C4 H4A 109.1 . . ? N1 C4 H4B 109.1 . . ? C5 C4 H4A 109.1 . . ? C5 C4 H4B 109.1 . . ? H4A C4 H4B 107.9 . . ? O2 C1 C2 117.52(9) . . ? O1 C1 O2 122.92(10) . . ? O1 C1 C2 119.56(9) . . ? C1 C2 H2A 108.5 . . ? C1 C2 H2B 108.5 . . ? C1 C2 C3 114.91(9) . . ? H2A C2 H2B 107.5 . . ? C3 C2 H2A 108.5 . . ? C3 C2 H2B 108.5 . . ? C2 C3 C3 112.03(11) . 3_667 ? C2 C3 H3A 109.2 . . ? C2 C3 H3B 109.2 . . ? C3 C3 H3A 109.2 3_667 . ? C3 C3 H3B 109.2 3_667 . ? H3A C3 H3B 107.9 . . ? O5 C9 H9A 110.0 . . ? O5 C9 H9B 110.0 . . ? O5 C9 C8 108.29(9) . . ? H9A C9 H9B 108.4 . . ? C8 C9 H9A 110.0 . . ? C8 C9 H9B 110.0 . . ? N1 C8 C9 110.25(9) . . ? N1 C8 H8A 109.6 . . ? N1 C8 H8B 109.6 . . ? C9 C8 H8A 109.6 . . ? C9 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? N1 C6 C7 110.50(9) . . ? H6A C6 H6B 108.1 . . ? C7 C6 H6A 109.5 . . ? C7 C6 H6B 109.5 . . ? O4 C7 C6 110.34(8) . . ? O4 C7 H7A 109.6 . . ? O4 C7 H7B 109.6 . . ? C6 C7 H7A 109.6 . . ? C6 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? 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 O3 C5 1.4199(13) . ? O3 H3 0.846(18) . ? O5 C9 1.4218(14) . ? O5 H5 0.900(19) . ? O2 C1 1.2736(13) . ? O1 C1 1.2525(13) . ? O4 C7 1.4188(13) . ? O4 H4 0.883(18) . ? N1 C4 1.5009(13) . ? N1 C8 1.5039(13) . ? N1 C6 1.5051(13) . ? N1 H1 0.920(14) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C5 C4 1.5086(15) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C1 C2 1.5217(15) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.5242(15) . ? C3 C3 1.528(2) 3_667 ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C9 C8 1.5167(15) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C6 C7 1.5201(16) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? 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 O3 C5 C4 N1 -52.16(11) . . . . ? O5 C9 C8 N1 -53.69(11) . . . . ? O2 C1 C2 C3 165.33(9) . . . . ? O1 C1 C2 C3 -14.76(14) . . . . ? N1 C6 C7 O4 -48.97(12) . . . . ? C4 N1 C8 C9 161.56(8) . . . . ? C4 N1 C6 C7 -73.65(11) . . . . ? C1 C2 C3 C3 -172.39(11) . . . 3_667 ? C8 N1 C4 C5 -64.21(11) . . . . ? C8 N1 C6 C7 158.95(9) . . . . ? C6 N1 C4 C5 169.12(9) . . . . ? C6 N1 C8 C9 -72.69(11) . . . . ?