#------------------------------------------------------------------------------ #$Date: 2023-12-04 20:14:58 +0200 (Mon, 04 Dec 2023) $ #$Revision: 288016 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/78/7247818.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_7247818 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 C9H8O4 _chemical_formula_sum 'C9 H8 O4' _chemical_formula_weight 180.15 _chemical_melting_point 409 _chemical_name_common Aspirin _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.cc2bk69f _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2022-03-23 deposited with the CCDC. 2023-10-20 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 111.627(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.2633(15) _cell_length_b 6.5624(8) _cell_length_c 11.4726(14) _cell_measurement_reflns_used 6070 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 22.30 _cell_measurement_theta_min 3.57 _cell_volume 858.28(18) _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 0.998 _diffrn_measurement_device_type 'Bruker APEX-III CMOS PHOTON DECTECTOR' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1492 _diffrn_reflns_av_unetI/netI 0.0589 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _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 51801 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.246 _diffrn_reflns_theta_min 3.572 _diffrn_source 'Sealed micro focustube' _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'R.H.Blessing Acta Crystallogr.A 1995,51,33' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.394 _exptl_crystal_description platy _exptl_crystal_F_000 376 _exptl_crystal_recrystallization_method 'Solution Crystallization process' _exptl_crystal_size_max 0.020 _exptl_crystal_size_mid 0.010 _exptl_crystal_size_min 0.005 _exptl_transmission_factor_max 0.9990 _exptl_transmission_factor_min 0.9980 _refine_diff_density_max 0.514 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.058 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 120 _refine_ls_number_reflns 1915 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.012 _refine_ls_R_factor_all 0.1545 _refine_ls_R_factor_gt 0.0748 _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^)+(0.0986P)^2^+0.4457P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1681 _refine_ls_wR_factor_ref 0.2056 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1016 _reflns_number_total 1915 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00611e2.cif _cod_data_source_block ID1215MAmonop_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_sg_symbol_H-M 'P 21/c' _cod_database_code 7247818 _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 0.998 _shelx_estimated_absorpt_t_max 0.999 _shelx_res_file ; TITL ID1215MAmonop_a.res in P2(1)/c ID1215MAmonop_a.res created by SHELXL-2016/6 at 19:35:23 on 27-Dec-2021 CELL 0.71073 12.2633 6.5624 11.4726 90.000 111.627 90.000 ZERR 4.000 0.0015 0.0008 0.0014 0.000 0.003 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H O UNIT 36 32 16 REM Old TITL ID1215MAmonop in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.195, Rweak 0.070, Alpha 0.073, Orientation as input REM Formula found by SHELXT: C9 O4 L.S. 10 ACTA BOND $H FMAP 2 PLAN 20 SIZE 0.005 0.01 0.02 TEMP 23.000 HTAB CONF WGHT 0.098600 0.445700 FVAR 0.87698 O3 3 0.784135 0.588175 0.727167 11.00000 0.05402 0.06021 = 0.03081 0.00096 0.01210 -0.00288 O2 3 0.619134 0.859506 0.608808 11.00000 0.05952 0.05796 = 0.04712 -0.01127 0.01248 0.01191 AFIX 147 H2 2 0.570366 0.949210 0.600880 11.00000 -1.50000 AFIX 0 O1 3 0.510139 0.810296 0.408179 11.00000 0.06656 0.06279 = 0.03949 -0.00118 0.00887 0.01358 O4 3 0.903968 0.780374 0.666054 11.00000 0.06423 0.07898 = 0.04533 -0.00753 0.02385 -0.01650 C7 1 0.590247 0.755721 0.505846 11.00000 0.03749 0.03752 = 0.03158 -0.00042 0.01005 -0.00400 C1 1 0.653360 0.564447 0.507287 11.00000 0.03986 0.04159 = 0.03625 -0.00006 0.01514 -0.00473 C8 1 0.864995 0.740401 0.743857 11.00000 0.04032 0.05355 = 0.03660 0.00016 0.00959 0.00172 C2 1 0.745212 0.486659 0.611011 11.00000 0.04720 0.04489 = 0.03988 0.00513 0.01550 -0.00417 C6 1 0.618179 0.449418 0.397887 11.00000 0.04589 0.05116 = 0.04099 -0.00106 0.01316 -0.00185 AFIX 43 H6 2 0.557147 0.496702 0.327348 11.00000 -1.20000 AFIX 0 C5 1 0.671434 0.266943 0.391217 11.00000 0.05441 0.04877 = 0.05024 -0.00811 0.01707 -0.00366 AFIX 43 H5 2 0.646873 0.192119 0.317169 11.00000 -1.20000 AFIX 0 C3 1 0.797820 0.303063 0.604770 11.00000 0.04797 0.06015 = 0.05000 0.00952 0.01385 0.00560 AFIX 43 H3 2 0.857916 0.251764 0.674751 11.00000 -1.20000 AFIX 0 C4 1 0.760364 0.198384 0.494641 11.00000 0.05752 0.05197 = 0.06462 -0.00099 0.02414 0.00385 AFIX 43 H4 2 0.796800 0.076005 0.490018 11.00000 -1.20000 AFIX 0 C9 1 0.895752 0.834740 0.868745 11.00000 0.06835 0.10619 = 0.04831 -0.02445 0.02228 -0.01167 AFIX 137 H9A 2 0.943935 0.952422 0.874373 11.00000 -1.50000 H9B 2 0.937945 0.738249 0.932248 11.00000 -1.50000 H9C 2 0.825371 0.874887 0.880813 11.00000 -1.50000 AFIX 0 HKLF 4 REM ID1215MAmonop_a.res in P2(1)/c REM R1 = 0.0748 for 1016 Fo > 4sig(Fo) and 0.1545 for all 1915 data REM 120 parameters refined using 0 restraints END WGHT 0.0986 0.4457 REM Instructions for potential hydrogen bonds EQIV $1 -x+1, -y+2, -z+1 HTAB O2 O1_$1 REM Highest difference peak 0.514, deepest hole -0.238, 1-sigma level 0.058 Q1 1 0.7788 0.9164 0.7286 11.00000 0.05 0.51 Q2 1 0.6201 0.6388 0.6114 11.00000 0.05 0.50 Q3 1 0.6583 0.9377 0.5190 11.00000 0.05 0.39 Q4 1 0.6179 0.0517 0.4026 11.00000 0.05 0.36 Q5 1 0.7435 0.0104 0.6123 11.00000 0.05 0.35 Q6 1 0.5040 0.6665 0.4081 11.00000 0.05 0.32 Q7 1 0.8985 0.6309 0.8686 11.00000 0.05 0.24 Q8 1 0.7810 0.1725 0.5837 11.00000 0.05 0.23 Q9 1 0.8565 -0.0798 0.5678 11.00000 0.05 0.17 Q10 1 0.9159 0.6892 0.6807 11.00000 0.05 0.17 Q11 1 0.7835 0.3405 0.4958 11.00000 0.05 0.15 Q12 1 0.8891 0.7609 0.9370 11.00000 0.05 0.15 Q13 1 0.5008 0.7730 0.3416 11.00000 0.05 0.15 Q14 1 0.8358 0.6547 0.9544 11.00000 0.05 0.14 Q15 1 0.9482 0.8473 0.6555 11.00000 0.05 0.14 Q16 1 0.6859 0.5856 0.6971 11.00000 0.05 0.14 Q17 1 0.8286 0.7272 0.9216 11.00000 0.05 0.14 Q18 1 1.0027 0.7232 0.6602 11.00000 0.05 0.12 Q19 1 1.0181 0.6582 0.8619 11.00000 0.05 0.12 Q20 1 0.9542 0.9095 0.7465 11.00000 0.05 0.12 ; _shelx_res_checksum 47272 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 0.78414(19) 0.5882(4) 0.72717(18) 0.0494(7) Uani 1 1 d . . . . . O2 O 0.6191(2) 0.8595(4) 0.6088(2) 0.0569(7) Uani 1 1 d . . . . . H2 H 0.570366 0.949210 0.600880 0.085 Uiso 1 1 calc R U . . . O1 O 0.5101(2) 0.8103(4) 0.4082(2) 0.0593(7) Uani 1 1 d . . . . . O4 O 0.9040(2) 0.7804(4) 0.6661(2) 0.0618(8) Uani 1 1 d . . . . . C7 C 0.5902(3) 0.7557(5) 0.5058(3) 0.0363(8) Uani 1 1 d . . . . . C1 C 0.6534(3) 0.5644(5) 0.5073(3) 0.0389(8) Uani 1 1 d . . . . . C8 C 0.8650(3) 0.7404(5) 0.7439(3) 0.0448(8) Uani 1 1 d . . . . . C2 C 0.7452(3) 0.4867(5) 0.6110(3) 0.0441(8) Uani 1 1 d . . . . . C6 C 0.6182(3) 0.4494(5) 0.3979(3) 0.0468(9) Uani 1 1 d . . . . . H6 H 0.557147 0.496702 0.327348 0.056 Uiso 1 1 calc R U . . . C5 C 0.6714(3) 0.2669(5) 0.3912(3) 0.0518(9) Uani 1 1 d . . . . . H5 H 0.646873 0.192119 0.317169 0.062 Uiso 1 1 calc R U . . . C3 C 0.7978(3) 0.3031(6) 0.6048(3) 0.0539(10) Uani 1 1 d . . . . . H3 H 0.857916 0.251764 0.674751 0.065 Uiso 1 1 calc R U . . . C4 C 0.7604(3) 0.1984(6) 0.4946(4) 0.0576(10) Uani 1 1 d . . . . . H4 H 0.796800 0.076005 0.490018 0.069 Uiso 1 1 calc R U . . . C9 C 0.8958(4) 0.8347(8) 0.8687(3) 0.0741(13) Uani 1 1 d . . . . . H9A H 0.943935 0.952422 0.874373 0.111 Uiso 1 1 calc R U . . . H9B H 0.937945 0.738249 0.932248 0.111 Uiso 1 1 calc R U . . . H9C H 0.825371 0.874887 0.880813 0.111 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 0.0540(14) 0.0602(16) 0.0308(12) 0.0010(11) 0.0121(10) -0.0029(12) O2 0.0595(16) 0.0580(17) 0.0471(14) -0.0113(12) 0.0125(12) 0.0119(12) O1 0.0666(16) 0.0628(17) 0.0395(14) -0.0012(12) 0.0089(13) 0.0136(13) O4 0.0642(16) 0.079(2) 0.0453(14) -0.0075(13) 0.0238(13) -0.0165(14) C7 0.0375(17) 0.0375(19) 0.0316(17) -0.0004(15) 0.0100(14) -0.0040(14) C1 0.0399(17) 0.0416(19) 0.0363(17) -0.0001(15) 0.0151(14) -0.0047(15) C8 0.0403(19) 0.054(2) 0.0366(19) 0.0002(16) 0.0096(15) 0.0017(16) C2 0.0472(19) 0.045(2) 0.0399(18) 0.0051(16) 0.0155(15) -0.0042(16) C6 0.0459(19) 0.051(2) 0.0410(19) -0.0011(16) 0.0132(15) -0.0019(17) C5 0.054(2) 0.049(2) 0.050(2) -0.0081(18) 0.0171(18) -0.0037(17) C3 0.048(2) 0.060(2) 0.050(2) 0.0095(19) 0.0139(17) 0.0056(18) C4 0.058(2) 0.052(2) 0.065(3) -0.001(2) 0.024(2) 0.0039(19) C9 0.068(3) 0.106(4) 0.048(2) -0.024(2) 0.022(2) -0.012(2) 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 116.9(2) . . ? C7 O2 H2 109.5 . . ? O1 C7 O2 122.1(3) . . ? O1 C7 C1 119.7(3) . . ? O2 C7 C1 118.2(3) . . ? C6 C1 C2 117.0(3) . . ? C6 C1 C7 117.8(3) . . ? C2 C1 C7 125.2(3) . . ? O4 C8 O3 121.8(3) . . ? O4 C8 C9 127.4(3) . . ? O3 C8 C9 110.7(3) . . ? C3 C2 C1 121.3(3) . . ? C3 C2 O3 117.4(3) . . ? C1 C2 O3 121.2(3) . . ? C5 C6 C1 121.7(3) . . ? C5 C6 H6 119.1 . . ? C1 C6 H6 119.1 . . ? C4 C5 C6 118.9(3) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? C4 C3 C2 119.0(3) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C5 C4 C3 122.1(4) . . ? C5 C4 H4 119.0 . . ? C3 C4 H4 119.0 . . ? 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 1.370(4) . ? O3 C2 1.407(4) . ? O2 C7 1.295(4) . ? O2 H2 0.8200 . ? O1 C7 1.240(4) . ? O4 C8 1.187(4) . ? C7 C1 1.472(4) . ? C1 C6 1.390(4) . ? C1 C2 1.399(4) . ? C8 C9 1.477(5) . ? C2 C3 1.381(5) . ? C6 C5 1.380(5) . ? C6 H6 0.9300 . ? C5 C4 1.359(5) . ? C5 H5 0.9300 . ? C3 C4 1.361(5) . ? C3 H3 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 O1 C7 C1 C6 -1.3(4) . . . . ? O2 C7 C1 C6 177.1(3) . . . . ? O1 C7 C1 C2 179.8(3) . . . . ? O2 C7 C1 C2 -1.7(4) . . . . ? C2 O3 C8 O4 -2.7(5) . . . . ? C2 O3 C8 C9 179.0(3) . . . . ? C6 C1 C2 C3 -0.4(4) . . . . ? C7 C1 C2 C3 178.5(3) . . . . ? C6 C1 C2 O3 -177.6(3) . . . . ? C7 C1 C2 O3 1.3(5) . . . . ? C8 O3 C2 C3 97.8(3) . . . . ? C8 O3 C2 C1 -84.9(3) . . . . ? C2 C1 C6 C5 -0.2(5) . . . . ? C7 C1 C6 C5 -179.2(3) . . . . ? C1 C6 C5 C4 0.2(5) . . . . ? C1 C2 C3 C4 1.1(5) . . . . ? O3 C2 C3 C4 178.4(3) . . . . ? C6 C5 C4 C3 0.6(6) . . . . ? C2 C3 C4 C5 -1.2(6) . . . . ?