#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/50/2105075.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2105075 loop_ _publ_author_name 'Mocilac, Pavle' 'Donnelly, Katie' 'Gallagher, John F.' _publ_section_title ; Structural systematics and conformational analyses of a 3 \\times 3 isomer grid of fluoro-N-(pyridyl)benzamides: physicochemical correlations, polymorphism and isomorphous relationships ; _journal_coeditor_code GP5047 _journal_issue 2 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 189 _journal_page_last 203 _journal_volume 68 _journal_year 2012 _chemical_formula_moiety 'C12 H9 F N2 O' _chemical_formula_sum 'C12 H9 F N2 O' _chemical_formula_weight 216.21 _chemical_melting_point 460 _chemical_name_common Fmp _chemical_name_systematic 3-Fluoro-N-(pyridin-4-yl)benzamide _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 94.2380(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.79610(10) _cell_length_b 11.3050(2) _cell_length_c 15.2384(2) _cell_measurement_reflns_used 5573 _cell_measurement_temperature 294.0(10) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 2.55 _cell_volume 995.76(3) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 294.0(10) _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.932 _diffrn_measurement_device 'Xcalibur, Sapphire3, Gemini Ultra' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0115 _diffrn_reflns_av_sigmaI/netI 0.0105 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 7728 _diffrn_reflns_theta_full 27.00 _diffrn_reflns_theta_max 27.80 _diffrn_reflns_theta_min 2.68 _diffrn_standards_decay_% 1 _diffrn_standards_interval_time 60 _diffrn_standards_number 7983 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_T_max 0.9799 _exptl_absorpt_correction_T_min 0.9614 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(ABSFAC, Clark and Reid, 1998)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.442 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 448 _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.19 _refine_diff_density_max 0.244 _refine_diff_density_min -0.167 _refine_ls_extinction_coef 0.010(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 150 _refine_ls_number_reflns 2202 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.050 _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0341 _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^)+(0.0410P)^2^+0.2546P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0891 _refine_ls_wR_factor_ref 0.0922 _reflns_number_gt 1988 _reflns_number_total 2202 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL 10-126 is Fmp in P21/c at RT with Mo at 40kV30mA to 0.80\%A [7-02] CELL 0.71073 5.7961 11.3050 15.2384 90.000 94.238 90.000 ZERR 4.00 0.0001 0.0002 0.0002 0.000 0.001 0.000 LATT 1 SYMM -X,1/2+Y,1/2-Z SFAC C H N O F UNIT 48 36 8 4 4 MERG 3 FMAP 2 L.S. 8 LIST 4 ACTA 54 CONF BOND $H HTAB EQIV $2 1-X,1/2+Y,1/2-Z EQIV $3 2-X,1-Y,1-Z EQIV $4 X,1/2-Y,1/2+Z HTAB N1 N24_$2 HTAB C26 O1 HTAB C14 C21_$4 HTAB C14 C22_$4 HTAB C14 C23_$4 HTAB C14 N24_$4 HTAB C14 C25_$4 HTAB C14 C26_$4 RTAB FC F13 C13 RTAB F13 C13_$3 RTAB CC C11 C1 RTAB CO C1 O1 RTAB CN C1 N1 RTAB CN C21 N1 RTAB NH N1 H1 RTAB CN C14 N24 RTAB CCO C11 C1 O1 RTAB CCN C11 C1 N1 RTAB NCO N1 C1 O1 RTAB CNC C21 N1 C1 RTAB CCN C22 C21 N1 RTAB CCN C26 C21 N1 RTAB CCC C12 C11 C1 RTAB CCC C16 C11 C1 RTAB CCC C14 C11 C1 RTAB NCN N24 C21 N1 RTAB OCCC O1 C1 C11 C12 RTAB OCCC O1 C1 C11 C16 RTAB CCNC C11 C1 N1 C21 RTAB CCCN C12 C11 C1 N1 RTAB CCCN C16 C11 C1 N1 RTAB CCNC C22 C21 N1 C1 RTAB CCNC C26 C21 N1 C1 SIZE 0.19 0.34 0.37 TEMP 21 PLAN 10 MPLA 6 C11 C12 C13 C14 C15 C16 MPLA 5 O1 N1 C1 C11 C21 MPLA 6 C21 C22 C23 N24 C25 C26 MPLA 6 C11 C12 C13 C14 C15 C16 MPLA 3 O1 N1 C1 C11 C21 MPLA 6 C21 C22 C23 N24 C25 C26 WGHT 0.041000 0.254600 EXTI 0.009685 FVAR 7.47539 MOLE 1 F13 5 1.175411 0.443098 0.571068 11.00000 0.07144 0.04697 = 0.08303 -0.02046 -0.01482 -0.00861 O1 4 1.086279 0.057923 0.402979 11.00000 0.03602 0.04005 = 0.05156 -0.01019 0.00667 0.00091 C1 1 0.894625 0.096793 0.413865 11.00000 0.03678 0.02761 = 0.02959 0.00214 0.00249 0.00132 N1 3 0.695892 0.059707 0.368149 11.00000 0.03692 0.03399 = 0.03900 -0.00809 -0.00337 0.00878 H1 2 0.581193 0.106716 0.368729 11.00000 0.04609 C11 1 0.859554 0.192368 0.479481 11.00000 0.03735 0.02981 = 0.02714 0.00182 -0.00190 0.00556 C12 1 1.036008 0.274660 0.494956 11.00000 0.03985 0.03449 = 0.03411 0.00054 -0.00186 0.00360 AFIX 43 H12 2 1.169658 0.271023 0.464842 11.00000 -1.20000 AFIX 0 C13 1 1.006697 0.361461 0.556103 11.00000 0.05319 0.03389 = 0.04366 -0.00532 -0.01298 0.00295 C14 1 0.813929 0.369133 0.603003 11.00000 0.06715 0.04863 = 0.04040 -0.01433 -0.00375 0.01933 AFIX 43 H14 2 0.799433 0.429215 0.643919 11.00000 -1.20000 AFIX 0 C15 1 0.642697 0.285706 0.587961 11.00000 0.05103 0.05981 = 0.04058 -0.00605 0.00783 0.01557 AFIX 43 H15 2 0.512076 0.288584 0.619859 11.00000 -1.20000 AFIX 0 C16 1 0.662460 0.197790 0.526095 11.00000 0.04044 0.04416 = 0.03744 -0.00019 0.00356 0.00407 AFIX 43 H16 2 0.544721 0.142552 0.515663 11.00000 -1.20000 AFIX 0 C21 1 0.671649 -0.033387 0.307904 11.00000 0.03607 0.02850 = 0.02795 0.00121 0.00347 -0.00035 C22 1 0.463937 -0.042920 0.256150 11.00000 0.03454 0.03479 = 0.04176 -0.00206 0.00003 0.00443 AFIX 43 H22 2 0.347233 0.012648 0.260963 11.00000 -1.20000 AFIX 0 C23 1 0.433672 -0.135414 0.197927 11.00000 0.03763 0.04180 = 0.04278 -0.00455 -0.00550 -0.00097 AFIX 43 H23 2 0.294532 -0.139561 0.163527 11.00000 -1.20000 AFIX 0 N24 3 0.590926 -0.219931 0.187390 11.00000 0.04365 0.03829 = 0.03903 -0.00785 0.00028 -0.00084 C25 1 0.788950 -0.209005 0.237575 11.00000 0.04024 0.03465 = 0.03916 -0.00437 0.00312 0.00525 AFIX 43 H25 2 0.901843 -0.266312 0.231618 11.00000 -1.20000 AFIX 0 C26 1 0.839200 -0.119324 0.297592 11.00000 0.03472 0.03493 = 0.03431 -0.00201 -0.00107 0.00331 AFIX 43 H26 2 0.981203 -0.116514 0.330200 11.00000 -1.20000 HKLF 4 REM 10-126 is Fmp in P21/c at RT with Mo at 40kV30mA to 0.80\%A [7-02] REM R1 = 0.0341 for 1988 Fo > 4sig(Fo) and 0.0376 for all 2202 data REM 150 parameters refined using 0 restraints END WGHT 0.0409 0.2542 REM Highest difference peak 0.244, deepest hole -0.167, 1-sigma level 0.031 Q1 1 0.8740 0.1458 0.4490 11.00000 0.05 0.24 Q2 1 0.7264 -0.0947 0.3187 11.00000 0.05 0.18 Q3 1 1.0408 0.2959 0.5471 11.00000 0.05 0.18 Q4 1 0.8822 0.3872 0.5598 11.00000 0.05 0.17 Q5 1 0.9162 0.2467 0.4717 11.00000 0.05 0.17 Q6 1 0.5723 -0.0378 0.2838 11.00000 0.05 0.17 Q7 1 0.8358 -0.1385 0.2449 11.00000 0.05 0.17 Q8 1 0.9951 0.3216 0.5192 11.00000 0.05 0.17 Q9 1 0.7331 0.2193 0.4848 11.00000 0.05 0.16 Q10 1 0.5541 -0.0575 0.2974 11.00000 0.05 0.15 ; _[local]_cod_data_source_file gp5047.cif _[local]_cod_data_source_block Fmp-10-126 _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. '_exptl_absorpt_correction_type' value 'Analytical' changed to 'analytical' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2105075 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity F F13 1.17541(17) 0.44310(8) 0.57107(7) 0.0682(3) Uani d . 1 1 O O1 1.08628(14) 0.05792(8) 0.40298(6) 0.0424(2) Uani d . 1 1 C C1 0.89463(19) 0.09679(10) 0.41387(7) 0.0313(2) Uani d . 1 1 N N1 0.69589(18) 0.05971(9) 0.36815(7) 0.0369(2) Uani d . 1 1 H H1 0.581(3) 0.1067(14) 0.3687(10) 0.046(4) Uiso d . 1 1 C C11 0.85955(19) 0.19237(10) 0.47948(7) 0.0316(2) Uani d . 1 1 C C12 1.0360(2) 0.27466(10) 0.49496(8) 0.0364(3) Uani d . 1 1 H H12 1.1697 0.2710 0.4648 0.044 Uiso calc R 1 1 C C13 1.0067(2) 0.36146(11) 0.55610(9) 0.0444(3) Uani d . 1 1 C C14 0.8139(3) 0.36913(13) 0.60300(9) 0.0524(4) Uani d . 1 1 H H14 0.7994 0.4292 0.6439 0.063 Uiso calc R 1 1 C C15 0.6427(2) 0.28571(14) 0.58796(9) 0.0502(3) Uani d . 1 1 H H15 0.5121 0.2886 0.6199 0.060 Uiso calc R 1 1 C C16 0.6625(2) 0.19779(12) 0.52609(8) 0.0406(3) Uani d . 1 1 H H16 0.5447 0.1426 0.5157 0.049 Uiso calc R 1 1 C C21 0.67165(19) -0.03339(9) 0.30790(7) 0.0308(2) Uani d . 1 1 C C22 0.4639(2) -0.04292(10) 0.25615(8) 0.0372(3) Uani d . 1 1 H H22 0.3472 0.0126 0.2610 0.045 Uiso calc R 1 1 C C23 0.4337(2) -0.13541(11) 0.19793(8) 0.0412(3) Uani d . 1 1 H H23 0.2945 -0.1396 0.1635 0.049 Uiso calc R 1 1 N N24 0.59093(18) -0.21993(9) 0.18739(7) 0.0405(3) Uani d . 1 1 C C25 0.7890(2) -0.20900(10) 0.23757(8) 0.0380(3) Uani d . 1 1 H H25 0.9018 -0.2663 0.2316 0.046 Uiso calc R 1 1 C C26 0.83920(19) -0.11932(10) 0.29759(7) 0.0348(3) Uani d . 1 1 H H26 0.9812 -0.1165 0.3302 0.042 Uiso calc R 1 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F13 0.0714(6) 0.0470(5) 0.0830(7) -0.0086(4) -0.0148(5) -0.0205(4) O1 0.0360(4) 0.0400(5) 0.0516(5) 0.0009(3) 0.0067(4) -0.0102(4) C1 0.0368(6) 0.0276(5) 0.0296(5) 0.0013(4) 0.0025(4) 0.0021(4) N1 0.0369(5) 0.0340(5) 0.0390(5) 0.0088(4) -0.0034(4) -0.0081(4) C11 0.0373(6) 0.0298(5) 0.0271(5) 0.0056(4) -0.0019(4) 0.0018(4) C12 0.0398(6) 0.0345(6) 0.0341(6) 0.0036(5) -0.0019(5) 0.0005(5) C13 0.0532(7) 0.0339(6) 0.0437(7) 0.0029(5) -0.0130(6) -0.0053(5) C14 0.0672(9) 0.0486(8) 0.0404(7) 0.0193(7) -0.0037(6) -0.0143(6) C15 0.0510(7) 0.0598(9) 0.0406(7) 0.0156(6) 0.0078(6) -0.0060(6) C16 0.0404(6) 0.0442(7) 0.0374(6) 0.0041(5) 0.0036(5) -0.0002(5) C21 0.0361(5) 0.0285(5) 0.0280(5) -0.0003(4) 0.0035(4) 0.0012(4) C22 0.0345(6) 0.0348(6) 0.0418(6) 0.0044(5) 0.0000(5) -0.0021(5) C23 0.0376(6) 0.0418(7) 0.0428(6) -0.0010(5) -0.0055(5) -0.0045(5) N24 0.0437(6) 0.0383(5) 0.0390(5) -0.0008(4) 0.0003(4) -0.0079(4) C25 0.0402(6) 0.0347(6) 0.0392(6) 0.0052(5) 0.0031(5) -0.0044(5) C26 0.0347(6) 0.0349(6) 0.0343(6) 0.0033(5) -0.0011(4) -0.0020(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' F F 0.0171 0.0103 '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 O1 C1 N1 124.25(10) O1 C1 C11 121.48(10) N1 C1 C11 114.27(9) C1 N1 C21 127.30(10) C1 N1 H1 115.6(10) C21 N1 H1 115.9(10) C12 C11 C16 120.39(11) C12 C11 C1 117.53(10) C16 C11 C1 122.04(11) C13 C12 C11 117.86(11) C13 C12 H12 121.1 C11 C12 H12 121.1 F13 C13 C12 118.58(13) F13 C13 C14 118.39(12) C12 C13 C14 123.02(13) C13 C14 C15 118.34(12) C13 C14 H14 120.8 C15 C14 H14 120.8 C14 C15 C16 120.80(13) C14 C15 H15 119.6 C16 C15 H15 119.6 C15 C16 C11 119.56(12) C15 C16 H16 120.2 C11 C16 H16 120.2 C26 C21 C22 117.60(10) C26 C21 N1 124.29(10) C22 C21 N1 118.09(10) C23 C22 C21 119.20(11) C23 C22 H22 120.4 C21 C22 H22 120.4 N24 C23 C22 124.41(11) N24 C23 H23 117.8 C22 C23 H23 117.8 C25 N24 C23 115.40(10) N24 C25 C26 125.19(11) N24 C25 H25 117.4 C26 C25 H25 117.4 C25 C26 C21 118.20(10) C25 C26 H26 120.9 C21 C26 H26 120.9 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F13 C13 1.3517(16) O1 C1 1.2173(13) C1 N1 1.3672(15) C1 C11 1.4962(15) N1 C21 1.3968(14) N1 H1 0.852(15) C11 C12 1.3898(16) C11 C16 1.3904(16) C12 C13 1.3724(17) C12 H12 0.9300 C13 C14 1.373(2) C14 C15 1.376(2) C14 H14 0.9300 C15 C16 1.3805(18) C15 H15 0.9300 C16 H16 0.9300 C21 C26 1.3908(15) C21 C22 1.3938(16) C22 C23 1.3742(17) C22 H22 0.9300 C23 N24 1.3383(16) C23 H23 0.9300 N24 C25 1.3371(16) C25 C26 1.3819(16) C25 H25 0.9300 C26 H26 0.9300 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 N24 2_655 0.852(15) 2.333(16) 3.0786(14) 146.5(13) yes C26 H26 O1 . 0.93 2.32 2.8819(14) 118 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 O1 C1 N1 C21 5.86(19) C11 C1 N1 C21 -174.83(10) O1 C1 C11 C12 31.61(15) N1 C1 C11 C12 -147.72(10) O1 C1 C11 C16 -146.23(12) N1 C1 C11 C16 34.44(15) C16 C11 C12 C13 -1.08(17) C1 C11 C12 C13 -178.96(10) C11 C12 C13 F13 -179.14(10) C11 C12 C13 C14 1.00(19) F13 C13 C14 C15 -179.75(12) C12 C13 C14 C15 0.1(2) C13 C14 C15 C16 -1.2(2) C14 C15 C16 C11 1.1(2) C12 C11 C16 C15 0.08(18) C1 C11 C16 C15 177.86(11) C1 N1 C21 C26 13.64(18) C1 N1 C21 C22 -168.08(11) C26 C21 C22 C23 -0.01(17) N1 C21 C22 C23 -178.41(11) C21 C22 C23 N24 0.8(2) C22 C23 N24 C25 -0.83(19) C23 N24 C25 C26 0.17(18) N24 C25 C26 C21 0.53(19) C22 C21 C26 C25 -0.58(16) N1 C21 C26 C25 177.71(11) _cod_database_fobs_code 2105075