#------------------------------------------------------------------------------ #$Date: 2019-11-24 03:22:50 +0200 (Sun, 24 Nov 2019) $ #$Revision: 236472 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/40/1554036.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_1554036 loop_ _publ_author_name 'Manin, Alex N.' 'Voronin, Alexander P.' 'Shishkina, Anastasia V.' 'Vener, Mikhail V.' 'Churakov, Andrei V.' 'Perlovich, German L.' _publ_section_title ; Influence of Secondary Interactions on the Structure, Sublimation Thermodynamics, and Solubility of Salicylate:4-Hydroxybenzamide Cocrystals. Combined Experimental and Theoretical Study. ; _journal_issue 33 _journal_name_full 'The journal of physical chemistry. B' _journal_page_first 10466 _journal_page_last 10477 _journal_paper_doi 10.1021/acs.jpcb.5b05082 _journal_volume 119 _journal_year 2015 _chemical_formula_moiety 'C7 H7 N O3, C7 H7 N O2' _chemical_formula_sum 'C11 H5 N2 O5 a' _chemical_formula_weight 290.27 _space_group_IT_number 29 _space_group_name_Hall 'P 2c -2ac' _space_group_name_H-M_alt 'P c a 21' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2ac' _symmetry_space_group_name_H-M 'P c a 21' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 32.1000(15) _cell_length_b 4.1188(2) _cell_length_c 9.6966(4) _cell_measurement_reflns_used 5183 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 29.984 _cell_measurement_theta_min 2.538 _cell_volume 1282.02(10) _computing_cell_refinement 'SAINT (Bruker, 2008)' _computing_data_collection 'SMART (Bruker, 2008)' _computing_data_reduction 'SAINT (Bruker, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker SMART 6K' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_max 44 _diffrn_reflns_limit_h_min -45 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 10583 _diffrn_reflns_theta_full 30.00 _diffrn_reflns_theta_max 30.00 _diffrn_reflns_theta_min 1.27 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_T_max 0.9828 _exptl_absorpt_correction_T_min 0.9772 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker, 2008)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.504 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 608 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.358 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.051 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 246 _refine_ls_number_reflns 1968 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.030 _refine_ls_R_factor_all 0.0356 _refine_ls_R_factor_gt 0.0333 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0675P)^2^+0.0940P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0866 _refine_ls_wR_factor_ref 0.0884 _reflns_number_gt 1857 _reflns_number_total 1968 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL d in Pca2(1) CELL 0.71073 32.1000 4.1188 9.6966 90.000 90.000 90.000 ZERR 4.00 0.0015 0.0002 0.0004 0.000 0.000 0.000 LATT -1 SYMM -X, -Y, 0.5+Z SYMM 0.5+X, -Y, Z SYMM 0.5-X, Y, 0.5+Z SFAC C H N O UNIT 56 56 8 20 TEMP -153 SIZE .15 .20 .20 EQIV $1 1-x, 2-y, 0.5+z EQIV $2 0.5+x, 1-y, z EQIV $3 -0.5+x, 2-y, z EQIV $4 0.5-x, -1+y, -0.5+z HTAB N1 O2 HTAB N1 O4_$1 HTAB O5 N2_$2 HTAB N2 O5_$3 HTAB N2 O3_$4 HTAB O1 O4 HTAB O3 O2 MPLA 6 C8 > C13 MPLA 3 N1 O4 C14 MPLA 6 C1 > C6 N2 H2a H2b MPLA 3 O2 O1 C7 CONF H2a N2 C4 C3 CONF H2b N2 C4 C5 L.S. 10 BOND $H ACTA FMAP 2 PLAN 8 OMIT -2 60 MERG 3 WGHT 0.067500 0.094000 FVAR 0.67962 N1 3 0.485080 0.914616 0.656618 11.00000 0.01450 0.04551 = 0.01914 -0.00497 0.00182 -0.00587 O4 4 0.489122 0.724884 0.438714 11.00000 0.01549 0.03822 = 0.02069 -0.00393 0.00070 -0.00443 O5 4 0.676368 1.190085 0.520947 11.00000 0.01289 0.02406 = 0.02299 -0.00117 0.00049 -0.00212 C8 1 0.550546 0.956994 0.533874 11.00000 0.01233 0.02142 = 0.01728 0.00314 -0.00005 0.00050 C9 1 0.575336 0.831980 0.427948 11.00000 0.01510 0.02076 = 0.01665 0.00109 -0.00100 -0.00097 C10 1 0.617555 0.904671 0.421542 11.00000 0.01515 0.02077 = 0.01643 0.00107 0.00149 0.00046 C11 1 0.635173 1.107035 0.520825 11.00000 0.01260 0.01744 = 0.01907 0.00426 -0.00134 -0.00029 C12 1 0.610486 1.237737 0.625132 11.00000 0.01689 0.01981 = 0.01789 -0.00056 -0.00040 -0.00173 C13 1 0.568521 1.161982 0.631991 11.00000 0.01583 0.02221 = 0.01778 0.00168 0.00097 0.00132 C14 1 0.506082 0.859239 0.540428 11.00000 0.01342 0.02734 = 0.01788 0.00302 0.00032 -0.00140 H1a 2 0.457251 0.865153 0.661814 11.00000 0.04076 H5a 2 0.688992 1.061020 0.474219 11.00000 0.03441 H1b 2 0.495755 0.996170 0.726132 11.00000 0.04496 H9 2 0.562784 0.687739 0.359325 11.00000 0.02656 H10 2 0.634649 0.805280 0.350442 11.00000 0.02191 H12 2 0.623526 1.391605 0.689535 11.00000 0.02453 H13 2 0.551840 1.262461 0.709644 11.00000 0.02856 N2 3 0.223068 0.252097 0.379052 11.00000 0.01435 0.02397 = 0.02058 -0.00006 -0.00192 0.00017 O2 4 0.399466 0.687404 0.627117 11.00000 0.01651 0.03968 = 0.02010 -0.00600 0.00123 -0.00416 O1 4 0.418758 0.426972 0.433832 11.00000 0.01328 0.03414 = 0.02297 -0.00428 0.00340 -0.00223 O3 4 0.321516 0.741450 0.684553 11.00000 0.01525 0.02806 = 0.01830 -0.00663 0.00181 -0.00285 C1 1 0.347535 0.430557 0.491743 11.00000 0.01302 0.01795 = 0.01709 0.00111 0.00216 -0.00136 C2 1 0.314604 0.555692 0.571318 11.00000 0.01505 0.01762 = 0.01497 0.00060 0.00085 -0.00061 C3 1 0.273397 0.492756 0.534783 11.00000 0.01339 0.01913 = 0.01725 0.00103 0.00143 0.00064 C4 1 0.264698 0.309983 0.417396 11.00000 0.01367 0.01765 = 0.01746 0.00150 -0.00085 -0.00208 C5 1 0.297344 0.175445 0.339197 11.00000 0.01783 0.02113 = 0.01762 -0.00063 0.00094 -0.00192 C6 1 0.338113 0.237519 0.376805 11.00000 0.01590 0.01862 = 0.01719 0.00122 0.00278 -0.00084 C7 1 0.390707 0.523136 0.523498 11.00000 0.01420 0.02394 = 0.01691 0.00194 0.00100 -0.00095 H2a 2 0.207879 0.424439 0.397512 11.00000 0.03597 H2b 2 0.220594 0.209472 0.291090 11.00000 0.03424 H3a 2 0.348604 0.743449 0.690914 11.00000 0.03473 H1 2 0.440440 0.542563 0.449488 11.00000 0.04764 H3 2 0.250666 0.579449 0.590374 11.00000 0.02307 H5 2 0.291834 0.045596 0.265367 11.00000 0.03278 H6 2 0.360294 0.143679 0.323400 11.00000 0.03034 HKLF 4 REM d in Pca2(1) REM R1 = 0.0333 for 1857 Fo > 4sig(Fo) and 0.0356 for all 1968 data REM 246 parameters refined using 1 restraints END WGHT 0.0675 0.0941 REM Highest difference peak 0.358, deepest hole -0.165, 1-sigma level 0.051 Q1 1 0.3692 0.4885 0.5113 11.00000 0.05 0.36 Q2 1 0.3177 0.2162 0.3656 11.00000 0.05 0.36 Q3 1 0.5971 0.8555 0.4350 11.00000 0.05 0.36 Q4 1 0.3305 0.4970 0.5240 11.00000 0.05 0.35 Q5 1 0.5906 1.1748 0.6260 11.00000 0.05 0.34 Q6 1 0.2915 0.5207 0.5504 11.00000 0.05 0.34 Q7 1 0.5287 0.9199 0.5409 11.00000 0.05 0.29 Q8 1 0.3410 0.3450 0.4330 11.00000 0.05 0.28 ; _cod_data_source_file jp5b05082_si_002.cif _cod_data_source_block d _cod_original_formula_sum 'C11 H5a N2 O5' _cod_database_code 1554036 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, 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_symmetry_multiplicity _atom_site_calc_flag N1 N 0.48508(5) 0.9146(5) 0.65662(17) 0.0264(3) Uani 1 1 d O4 O 0.48912(4) 0.7249(3) 0.43871(15) 0.0248(3) Uani 1 1 d O5 O 0.67637(4) 1.1901(3) 0.52095(14) 0.0200(3) Uani 1 1 d C8 C 0.55055(5) 0.9570(4) 0.53387(18) 0.0170(3) Uani 1 1 d C9 C 0.57534(5) 0.8320(4) 0.42795(18) 0.0175(3) Uani 1 1 d C10 C 0.61755(5) 0.9047(4) 0.42154(17) 0.0175(3) Uani 1 1 d C11 C 0.63517(5) 1.1070(4) 0.52083(17) 0.0164(3) Uani 1 1 d C12 C 0.61049(5) 1.2377(4) 0.62513(19) 0.0182(3) Uani 1 1 d C13 C 0.56852(5) 1.1620(4) 0.63199(18) 0.0186(3) Uani 1 1 d C14 C 0.50608(5) 0.8592(4) 0.54043(18) 0.0195(3) Uani 1 1 d H1a H 0.4573(9) 0.865(8) 0.662(4) 0.041(8) Uiso 1 1 d H5a H 0.6890(9) 1.061(7) 0.474(3) 0.034(7) Uiso 1 1 d H1b H 0.4958(10) 0.996(9) 0.726(4) 0.045(8) Uiso 1 1 d H9 H 0.5628(8) 0.688(6) 0.359(3) 0.027(6) Uiso 1 1 d H10 H 0.6346(8) 0.805(5) 0.350(3) 0.022(6) Uiso 1 1 d H12 H 0.6235(7) 1.392(6) 0.690(3) 0.025(6) Uiso 1 1 d H13 H 0.5518(8) 1.262(6) 0.710(3) 0.029(7) Uiso 1 1 d N2 N 0.22307(5) 0.2521(4) 0.37905(18) 0.0196(3) Uani 1 1 d O2 O 0.39947(4) 0.6874(4) 0.62712(15) 0.0254(3) Uani 1 1 d O1 O 0.41876(4) 0.4270(3) 0.43383(15) 0.0235(3) Uani 1 1 d O3 O 0.32152(4) 0.7414(3) 0.68455(14) 0.0205(3) Uani 1 1 d C1 C 0.34753(5) 0.4306(4) 0.49174(17) 0.0160(3) Uani 1 1 d C2 C 0.31460(5) 0.5557(4) 0.57132(17) 0.0159(3) Uani 1 1 d C3 C 0.27340(5) 0.4928(4) 0.53478(18) 0.0166(3) Uani 1 1 d C4 C 0.26470(5) 0.3100(4) 0.41740(18) 0.0163(3) Uani 1 1 d C5 C 0.29734(5) 0.1754(4) 0.33920(19) 0.0189(3) Uani 1 1 d C6 C 0.33811(5) 0.2375(4) 0.37680(18) 0.0172(3) Uani 1 1 d C7 C 0.39071(5) 0.5231(4) 0.52350(17) 0.0184(3) Uani 1 1 d H2a H 0.2079(8) 0.424(6) 0.398(3) 0.036(7) Uiso 1 1 d H2b H 0.2206(9) 0.209(7) 0.291(3) 0.034(7) Uiso 1 1 d H3a H 0.3486(9) 0.743(7) 0.691(3) 0.035(7) Uiso 1 1 d H1 H 0.4404(10) 0.543(8) 0.449(4) 0.048(8) Uiso 1 1 d H3 H 0.2507(8) 0.579(5) 0.590(3) 0.023(5) Uiso 1 1 d H5 H 0.2918(8) 0.046(6) 0.265(3) 0.033(7) Uiso 1 1 d H6 H 0.3603(8) 0.144(6) 0.323(3) 0.030(6) 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 N1 0.0145(6) 0.0455(10) 0.0191(7) -0.0050(7) 0.0018(5) -0.0059(6) O4 0.0155(5) 0.0382(7) 0.0207(6) -0.0039(6) 0.0007(5) -0.0044(5) O5 0.0129(5) 0.0241(6) 0.0230(6) -0.0012(5) 0.0005(4) -0.0021(4) C8 0.0123(6) 0.0214(7) 0.0173(7) 0.0031(6) 0.0000(5) 0.0005(5) C9 0.0151(6) 0.0208(7) 0.0166(7) 0.0011(6) -0.0010(6) -0.0010(5) C10 0.0151(6) 0.0208(7) 0.0164(7) 0.0011(6) 0.0015(6) 0.0005(5) C11 0.0126(6) 0.0174(6) 0.0191(7) 0.0043(6) -0.0013(5) -0.0003(5) C12 0.0169(7) 0.0198(7) 0.0179(7) -0.0006(6) -0.0004(6) -0.0017(5) C13 0.0158(7) 0.0222(7) 0.0178(7) 0.0017(6) 0.0010(6) 0.0013(6) C14 0.0134(6) 0.0273(8) 0.0179(7) 0.0030(6) 0.0003(5) -0.0014(6) N2 0.0144(6) 0.0240(7) 0.0206(7) -0.0001(5) -0.0019(5) 0.0002(5) O2 0.0165(5) 0.0397(7) 0.0201(6) -0.0060(5) 0.0012(5) -0.0042(5) O1 0.0133(5) 0.0341(6) 0.0230(6) -0.0043(6) 0.0034(5) -0.0022(5) O3 0.0152(5) 0.0281(6) 0.0183(6) -0.0066(5) 0.0018(5) -0.0028(4) C1 0.0130(6) 0.0179(7) 0.0171(7) 0.0011(5) 0.0022(5) -0.0014(5) C2 0.0150(7) 0.0176(7) 0.0150(7) 0.0006(5) 0.0009(5) -0.0006(5) C3 0.0134(6) 0.0191(6) 0.0173(7) 0.0010(6) 0.0014(5) 0.0006(5) C4 0.0137(6) 0.0176(6) 0.0175(7) 0.0015(6) -0.0008(5) -0.0021(5) C5 0.0178(7) 0.0211(7) 0.0176(7) -0.0006(6) 0.0009(6) -0.0019(6) C6 0.0159(7) 0.0186(7) 0.0172(7) 0.0012(6) 0.0028(6) -0.0008(5) C7 0.0142(6) 0.0239(7) 0.0169(7) 0.0019(6) 0.0010(6) -0.0009(5) 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' 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 C14 N1 H1a 120(2) C14 N1 H1b 123(2) H1a N1 H1b 117(3) C11 O5 H5a 109(2) C13 C8 C9 119.21(14) C13 C8 C14 122.14(15) C9 C8 C14 118.62(15) C10 C9 C8 120.59(15) C10 C9 H9 120.1(16) C8 C9 H9 119.3(16) C9 C10 C11 119.60(15) C9 C10 H10 119.5(15) C11 C10 H10 120.9(15) O5 C11 C12 116.96(15) O5 C11 C10 122.91(14) C12 C11 C10 120.13(14) C13 C12 C11 120.09(16) C13 C12 H12 121.9(14) C11 C12 H12 117.9(14) C12 C13 C8 120.36(15) C12 C13 H13 117.3(15) C8 C13 H13 122.4(15) O4 C14 N1 121.36(15) O4 C14 C8 120.20(15) N1 C14 C8 118.44(16) C4 N2 H2a 109.6(18) C4 N2 H2b 112.2(19) H2a N2 H2b 108(3) C7 O1 H1 106(2) C2 O3 H3a 103(2) C6 C1 C2 118.80(14) C6 C1 C7 121.13(14) C2 C1 C7 119.90(15) O3 C2 C3 117.77(14) O3 C2 C1 121.86(14) C3 C2 C1 120.38(15) C4 C3 C2 119.90(14) C4 C3 H3 120.0(16) C2 C3 H3 120.1(16) C3 C4 C5 120.25(14) C3 C4 N2 119.85(15) C5 C4 N2 119.87(16) C6 C5 C4 119.34(16) C6 C5 H5 120.0(17) C4 C5 H5 120.7(17) C5 C6 C1 121.25(15) C5 C6 H6 119.0(16) C1 C6 H6 119.8(16) O2 C7 O1 122.97(15) O2 C7 C1 121.57(15) O1 C7 C1 115.44(15) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C14 1.333(2) N1 H1a 0.92(3) N1 H1b 0.83(4) O4 C14 1.255(2) O5 C11 1.3659(18) O5 H5a 0.81(3) C8 C13 1.397(2) C8 C9 1.398(2) C8 C14 1.484(2) C9 C10 1.389(2) C9 H9 0.98(3) C10 C11 1.393(2) C10 H10 0.97(3) C11 C12 1.393(2) C12 C13 1.384(2) C12 H12 0.98(3) C13 H13 1.01(3) N2 C4 1.407(2) N2 H2a 0.88(3) N2 H2b 0.87(3) O2 C7 1.244(2) O1 C7 1.313(2) O1 H1 0.86(3) O3 C2 1.357(2) O3 H3a 0.87(3) C1 C6 1.402(2) C1 C2 1.407(2) C1 C7 1.470(2) C2 C3 1.394(2) C3 C4 1.393(2) C3 H3 0.97(3) C4 C5 1.407(2) C5 C6 1.382(2) C5 H5 0.91(3) C6 H6 0.96(3) 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 N1 H1a O2 0.92(3) 2.02(3) 2.917(2) 165(3) . N1 H1b O4 0.83(4) 2.41(4) 3.221(2) 167(3) 2_675 O5 H5a N2 0.81(3) 1.93(3) 2.731(2) 174(3) 3_565 N2 H2a O5 0.88(3) 2.23(3) 3.069(2) 159(3) 3_475 N2 H2b O3 0.87(3) 2.57(3) 3.167(2) 126(2) 4_544 O1 H1 O4 0.86(3) 1.74(3) 2.5709(18) 164(4) . O3 H3a O2 0.87(3) 1.76(3) 2.5731(17) 154(3) . 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 H2a N2 C4 C3 36(2) H2b N2 C4 C5 -25(2)