#------------------------------------------------------------------------------ #$Date: 2023-12-04 20:14:58 +0200 (Mon, 04 Dec 2023) $ #$Revision: 288016 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/78/7247819.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_7247819 loop_ _publ_author_name 'Muthusamy, Ramya' 'Karuppannan, Srinivasan' _publ_section_title ; Liquid--liquid phase separation and crystallization of aspirin polymorphs from a water--acetonitrile mixed solvent medium through a swift cooling process ; _journal_issue 47 _journal_name_full CrystEngComm _journal_page_first 6611 _journal_page_last 6621 _journal_paper_doi 10.1039/D3CE00611E _journal_volume 25 _journal_year 2023 _chemical_formula_moiety 'C9 H8 04' _chemical_formula_sum 'C9 H8 O4' _chemical_formula_weight 180.15 _chemical_name_common 'Acetylsalicylic acid' _chemical_name_systematic 2-acetoxybenzoicacid _chemical_properties_physical Hygroscopic _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_block_doi 10.5517/ccdc.csd.cc2bnj5q _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2022-04-06 deposited with the CCDC. 2023-10-20 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 95.750(9) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.429(4) _cell_length_b 6.597(2) _cell_length_c 11.395(4) _cell_measurement_reflns_used 6570 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 22.47 _cell_measurement_theta_min 3.57 _cell_volume 854.8(5) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX3' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and Encifer' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Bruker APEX-III CMOS Photon Detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1422 _diffrn_reflns_av_unetI/netI 0.0535 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 45382 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.442 _diffrn_reflns_theta_min 3.570 _diffrn_source 'Sealed Microfocus Tube' _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'B.H.Blessings,Acta CrystalograA,1995,51,33' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.400 _exptl_crystal_description Prismatic _exptl_crystal_F_000 376 _exptl_crystal_recrystallization_method 'Solution-state crystallization method' _exptl_crystal_size_max 0.463 _exptl_crystal_size_mid 0.186 _exptl_crystal_size_min 0.030 _exptl_transmission_factor_max 0.9970 _exptl_transmission_factor_min 0.9500 _refine_diff_density_max 0.170 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.040 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 120 _refine_ls_number_reflns 1946 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.1119 _refine_ls_R_factor_gt 0.0524 _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^)+(0.0494P)^2^+0.2533P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1074 _refine_ls_wR_factor_ref 0.1245 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1141 _reflns_number_total 1946 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00611e2.cif _cod_data_source_block ASAMONOP_a _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-scan' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas ; _cod_original_cell_volume 854.9(5) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7247819 _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_min 0.950 _shelx_estimated_absorpt_t_max 0.997 _shelx_res_file ; TITL ASAMONOP_a.res in P2(1)/c ASAMONOP_a.res created by SHELXL-2016/6 at 08:05:17 on 04-Apr-2022 CELL 0.71073 11.4295 6.5971 11.3954 90.000 95.750 90.000 ZERR 4.000 0.0038 0.0022 0.0039 0.000 0.009 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H O UNIT 36 32 16 REM Old TITL ASAMONOP in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.160, Rweak 0.032, Alpha 0.042, Orientation as input REM Formula found by SHELXT: C9 O4 L.S. 10 ACTA BOND $H FMAP 2 PLAN 20 SIZE 0.03 0.186 0.463 TEMP 23.000 HTAB CONF WGHT 0.049400 0.253300 FVAR 0.89572 O3 3 0.214732 0.411345 0.587943 11.00000 0.04467 0.04794 = 0.03101 -0.00539 0.00754 -0.00386 O1 3 0.379826 0.140160 0.550848 11.00000 0.05459 0.05046 = 0.05130 0.01656 0.01674 0.01326 AFIX 147 H1 2 0.424304 0.043231 0.563006 11.00000 -1.50000 AFIX 0 O2 3 0.489549 0.187991 0.403427 11.00000 0.05965 0.05339 = 0.04864 0.00891 0.02208 0.01745 O4 3 0.096509 0.220491 0.465510 11.00000 0.06542 0.08063 = 0.03788 -0.00507 0.00321 -0.02684 C7 1 0.409747 0.242931 0.462126 11.00000 0.03649 0.04002 = 0.03038 -0.00220 0.00558 -0.00284 C1 1 0.347024 0.435735 0.432384 11.00000 0.03376 0.03731 = 0.03356 -0.00297 0.00300 -0.00262 C2 1 0.254234 0.512189 0.490451 11.00000 0.04034 0.03928 = 0.03109 -0.00477 0.00382 -0.00376 C6 1 0.383068 0.550060 0.340257 11.00000 0.03823 0.04479 = 0.04177 -0.00029 0.00747 -0.00012 AFIX 43 H6 2 0.444634 0.503086 0.300116 11.00000 -1.20000 AFIX 0 C8 1 0.134235 0.261662 0.563679 11.00000 0.03910 0.04849 = 0.03666 -0.00193 0.00781 0.00101 C3 1 0.202127 0.694006 0.458395 11.00000 0.04404 0.04451 = 0.05430 -0.00763 0.00976 0.00603 AFIX 43 H3 2 0.141326 0.743686 0.498672 11.00000 -1.20000 AFIX 0 C5 1 0.329978 0.731206 0.306821 11.00000 0.05055 0.04544 = 0.05050 0.00990 0.00912 -0.00129 AFIX 43 H5 2 0.354860 0.804659 0.244240 11.00000 -1.20000 AFIX 0 C4 1 0.240225 0.802280 0.366506 11.00000 0.05334 0.03786 = 0.06009 0.00345 0.00192 0.00420 AFIX 43 H4 2 0.204655 0.925207 0.344605 11.00000 -1.20000 AFIX 0 C9 1 0.102924 0.163360 0.673056 11.00000 0.05890 0.07740 = 0.04553 0.01113 0.01004 -0.00932 AFIX 137 H9A 2 0.047722 0.056069 0.653217 11.00000 -1.50000 H9B 2 0.068252 0.261654 0.721164 11.00000 -1.50000 H9C 2 0.172495 0.108610 0.715717 11.00000 -1.50000 AFIX 0 HKLF 4 REM ASAMONOP_a.res in P2(1)/c REM R1 = 0.0524 for 1141 Fo > 4sig(Fo) and 0.1119 for all 1946 data REM 120 parameters refined using 0 restraints END WGHT 0.0494 0.2533 REM Instructions for potential hydrogen bonds EQIV $1 -x+1, -y, -z+1 HTAB O1 O2_$1 REM Highest difference peak 0.170, deepest hole -0.194, 1-sigma level 0.040 Q1 1 0.1443 0.2381 0.7462 11.00000 0.05 0.17 Q2 1 0.1384 -0.0043 0.6581 11.00000 0.05 0.16 Q3 1 0.5093 0.2263 0.4612 11.00000 0.05 0.15 Q4 1 0.4665 -0.0722 0.5739 11.00000 0.05 0.14 Q5 1 0.1409 0.7162 0.4655 11.00000 0.05 0.14 Q6 1 0.3327 0.0641 0.4559 11.00000 0.05 0.14 Q7 1 0.3263 0.5016 0.4754 11.00000 0.05 0.14 Q8 1 0.0134 0.1374 0.6634 11.00000 0.05 0.13 Q9 1 -0.0126 0.2231 0.4577 11.00000 0.05 0.13 Q10 1 0.0801 -0.0930 0.7597 11.00000 0.05 0.13 Q11 1 0.1433 0.7191 0.2369 11.00000 0.05 0.12 Q12 1 0.4359 0.1570 0.3935 11.00000 0.05 0.12 Q13 1 0.0263 0.4068 0.3855 11.00000 0.05 0.12 Q14 1 0.3001 0.5791 0.1472 11.00000 0.05 0.12 Q15 1 0.3815 0.5522 0.4173 11.00000 0.05 0.12 Q16 1 0.3354 0.7528 0.1943 11.00000 0.05 0.12 Q17 1 0.3322 0.2640 0.5760 11.00000 0.05 0.12 Q18 1 0.2781 0.4162 0.4395 11.00000 0.05 0.12 Q19 1 0.0614 0.3426 0.4735 11.00000 0.05 0.11 Q20 1 0.4866 0.2585 0.3334 11.00000 0.05 0.11 ; _shelx_res_checksum 23689 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 0.21473(12) 0.4113(2) 0.58794(11) 0.0410(4) Uani 1 1 d . . . . . O1 O 0.37983(13) 0.1402(2) 0.55085(14) 0.0513(5) Uani 1 1 d . . . . . H1 H 0.424304 0.043231 0.563006 0.077 Uiso 1 1 calc R U . . . O2 O 0.48955(14) 0.1880(2) 0.40343(13) 0.0528(5) Uani 1 1 d . . . . . O4 O 0.09651(15) 0.2205(3) 0.46551(13) 0.0614(5) Uani 1 1 d . . . . . C7 C 0.40975(17) 0.2429(3) 0.46213(16) 0.0355(5) Uani 1 1 d . . . . . C1 C 0.34702(17) 0.4357(3) 0.43238(17) 0.0349(5) Uani 1 1 d . . . . . C2 C 0.25423(18) 0.5122(3) 0.49045(16) 0.0369(5) Uani 1 1 d . . . . . C6 C 0.38307(18) 0.5501(3) 0.34026(18) 0.0414(5) Uani 1 1 d . . . . . H6 H 0.444634 0.503086 0.300116 0.050 Uiso 1 1 calc R U . . . C8 C 0.13424(19) 0.2617(3) 0.56368(18) 0.0411(5) Uani 1 1 d . . . . . C3 C 0.20213(19) 0.6940(3) 0.4584(2) 0.0473(6) Uani 1 1 d . . . . . H3 H 0.141326 0.743686 0.498672 0.057 Uiso 1 1 calc R U . . . C5 C 0.3300(2) 0.7312(3) 0.3068(2) 0.0486(6) Uani 1 1 d . . . . . H5 H 0.354860 0.804659 0.244240 0.058 Uiso 1 1 calc R U . . . C4 C 0.2402(2) 0.8023(4) 0.3665(2) 0.0507(6) Uani 1 1 d . . . . . H4 H 0.204655 0.925207 0.344605 0.061 Uiso 1 1 calc R U . . . C9 C 0.1029(2) 0.1634(4) 0.6731(2) 0.0603(7) Uani 1 1 d . . . . . H9A H 0.047722 0.056069 0.653217 0.090 Uiso 1 1 calc R U . . . H9B H 0.068252 0.261654 0.721164 0.090 Uiso 1 1 calc R U . . . H9C H 0.172495 0.108610 0.715717 0.090 Uiso 1 1 calc R U . . . 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 0.0447(9) 0.0479(9) 0.0310(8) -0.0054(7) 0.0075(6) -0.0039(7) O1 0.0546(10) 0.0505(10) 0.0513(10) 0.0166(8) 0.0167(8) 0.0133(8) O2 0.0597(10) 0.0534(10) 0.0486(9) 0.0089(8) 0.0221(8) 0.0174(8) O4 0.0654(11) 0.0806(13) 0.0379(9) -0.0051(9) 0.0032(8) -0.0268(9) C7 0.0365(12) 0.0400(12) 0.0304(11) -0.0022(10) 0.0056(9) -0.0028(9) C1 0.0338(11) 0.0373(11) 0.0336(11) -0.0030(10) 0.0030(9) -0.0026(9) C2 0.0403(12) 0.0393(12) 0.0311(11) -0.0048(10) 0.0038(9) -0.0038(10) C6 0.0382(12) 0.0448(13) 0.0418(12) -0.0003(10) 0.0075(10) -0.0001(10) C8 0.0391(12) 0.0485(13) 0.0367(12) -0.0019(11) 0.0078(10) 0.0010(11) C3 0.0440(13) 0.0445(13) 0.0543(14) -0.0076(12) 0.0098(11) 0.0060(11) C5 0.0505(14) 0.0454(14) 0.0505(14) 0.0099(11) 0.0091(11) -0.0013(11) C4 0.0533(15) 0.0379(13) 0.0601(15) 0.0035(12) 0.0019(12) 0.0042(11) C9 0.0589(15) 0.0774(18) 0.0455(14) 0.0111(13) 0.0100(12) -0.0093(14) 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' 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 C8 O3 C2 116.55(15) . . ? C7 O1 H1 109.5 . . ? O2 C7 O1 122.44(19) . . ? O2 C7 C1 119.55(18) . . ? O1 C7 C1 118.00(17) . . ? C6 C1 C2 117.27(19) . . ? C6 C1 C7 117.75(17) . . ? C2 C1 C7 124.98(18) . . ? C3 C2 C1 121.23(19) . . ? C3 C2 O3 117.27(18) . . ? C1 C2 O3 121.41(18) . . ? C5 C6 C1 121.66(19) . . ? C5 C6 H6 119.2 . . ? C1 C6 H6 119.2 . . ? O4 C8 O3 122.11(19) . . ? O4 C8 C9 126.6(2) . . ? O3 C8 C9 111.27(18) . . ? C2 C3 C4 119.7(2) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C4 C5 C6 119.4(2) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C5 C4 C3 120.7(2) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? 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 C8 1.359(3) . ? O3 C2 1.408(2) . ? O1 C7 1.292(2) . ? O1 H1 0.8200 . ? O2 C7 1.238(2) . ? O4 C8 1.189(2) . ? C7 C1 1.483(3) . ? C1 C6 1.388(3) . ? C1 C2 1.399(3) . ? C2 C3 1.372(3) . ? C6 C5 1.377(3) . ? C6 H6 0.9300 . ? C8 C9 1.480(3) . ? C3 C4 1.374(3) . ? C3 H3 0.9300 . ? C5 C4 1.369(3) . ? C5 H5 0.9300 . ? C4 H4 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? 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 O2 C7 C1 C6 -1.5(3) . . . . ? O1 C7 C1 C6 177.19(19) . . . . ? O2 C7 C1 C2 178.78(19) . . . . ? O1 C7 C1 C2 -2.5(3) . . . . ? C6 C1 C2 C3 -0.8(3) . . . . ? C7 C1 C2 C3 178.96(19) . . . . ? C6 C1 C2 O3 -177.37(17) . . . . ? C7 C1 C2 O3 2.4(3) . . . . ? C8 O3 C2 C3 97.9(2) . . . . ? C8 O3 C2 C1 -85.4(2) . . . . ? C2 C1 C6 C5 -0.1(3) . . . . ? C7 C1 C6 C5 -179.85(19) . . . . ? C2 O3 C8 O4 -1.8(3) . . . . ? C2 O3 C8 C9 178.11(18) . . . . ? C1 C2 C3 C4 1.0(3) . . . . ? O3 C2 C3 C4 177.7(2) . . . . ? C1 C6 C5 C4 0.8(3) . . . . ? C6 C5 C4 C3 -0.6(4) . . . . ? C2 C3 C4 C5 -0.3(4) . . . . ?