#------------------------------------------------------------------------------ #$Date: 2012-05-05 11:59:23 +0100 (Sat, 05 May 2012) $ #$Revision: 55466 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/50/2105077.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_2105077 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 421 _chemical_name_common Fpm_O _chemical_name_systematic 4-Fluoro-N-(pyridin-3-yl)benzamide _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 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 114.812(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 13.9411(3) _cell_length_b 5.20400(10) _cell_length_c 15.0752(3) _cell_measurement_reflns_used 6156 _cell_measurement_temperature 294.0(10) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 2.55 _cell_volume 992.74(4) _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 0.998 _diffrn_measured_fraction_theta_max 0.942 _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 0.0117 _diffrn_reflns_av_sigmaI/netI 0.0108 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 8861 _diffrn_reflns_theta_full 27.00 _diffrn_reflns_theta_max 29.58 _diffrn_reflns_theta_min 2.61 _diffrn_standards_decay_% 1 _diffrn_standards_interval_time 60 _diffrn_standards_number 9494 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_T_max 0.9664 _exptl_absorpt_correction_T_min 0.9472 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(ABSFAC, Clark and Reid, 1998)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 448 _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.49 _exptl_crystal_size_min 0.32 _refine_diff_density_max 0.251 _refine_diff_density_min -0.191 _refine_ls_extinction_coef 0.012(3) _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 1.032 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 150 _refine_ls_number_reflns 2624 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.032 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0415 _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^)+(0.0519P)^2^+0.3065P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1096 _refine_ls_wR_factor_ref 0.1135 _reflns_number_gt 2338 _reflns_number_total 2624 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL 10-127 is Fpm in P21/n at RT with Mo at 40kV30mA to 0.75\%A [8-06] CELL 0.71073 13.9411 5.2040 15.0752 90.000 114.812 90.000 ZERR 4 0.0003 0.0001 0.0003 0.000 0.003 0.000 LATT 1 SYMM 1/2-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 X,1+Y,Z EQIV $3 2-X,-Y,-Z EQIV $4 1/2+X,1/2-Y,-1/2+Z EQIV $5 1-X,1-Y,-Z EQIV $6 1/2-X,-1/2+Y,1/2-Z HTAB N1 O1_$2 HTAB F14 F14_$3 HTAB F14 C24_$4 HTAB C26 O1 HTAB C15 N23_$5 HTAB C24 N23_$6 RTAB CC C11 C1 RTAB CO C1 O1 RTAB CN C1 N1 RTAB CN C21 N1 RTAB NH N1 H1 RTAB CC C14 C24 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 N23 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 0.32 0.49 0.51 TEMP 21 PLAN 10 MPLA 6 C11 C12 C13 C14 C15 C16 F14 N23 MPLA 5 O1 N1 C1 C11 C21 F14 N23 MPLA 6 C21 C22 N23 C24 C25 C26 F14 MPLA 6 C11 C12 C13 C14 C15 C16 MPLA 3 O1 N1 C1 C11 C21 MPLA 6 C21 C22 N23 C24 C25 C26 WGHT 0.051900 0.306500 EXTI 0.012377 FVAR 10.19682 MOLE 1 F14 5 0.900212 0.134605 -0.046767 11.00000 0.05820 0.08345 = 0.07966 0.02490 0.05144 0.01524 O1 4 0.615949 -0.333398 0.142797 11.00000 0.07687 0.02457 = 0.09173 0.00117 0.06207 0.00049 C1 1 0.630292 -0.107257 0.129021 11.00000 0.03722 0.02668 = 0.04071 -0.00027 0.02079 0.00010 N1 3 0.582458 0.088784 0.153403 11.00000 0.03994 0.02401 = 0.04670 0.00113 0.02730 -0.00056 H1 2 0.597580 0.242793 0.143091 11.00000 0.04433 C11 1 0.702514 -0.031055 0.083257 11.00000 0.03331 0.02788 = 0.03404 -0.00234 0.01692 0.00045 C12 1 0.788447 -0.189034 0.098441 11.00000 0.03624 0.03423 = 0.03941 0.00487 0.01668 0.00633 AFIX 43 H12 2 0.800165 -0.334142 0.137627 11.00000 -1.20000 AFIX 0 C13 1 0.856722 -0.132854 0.055928 11.00000 0.03449 0.04662 = 0.04996 0.00527 0.02072 0.01114 AFIX 43 H13 2 0.915150 -0.235989 0.067079 11.00000 -1.20000 AFIX 0 C14 1 0.835642 0.079643 -0.003194 11.00000 0.03691 0.04835 = 0.04183 0.00134 0.02379 0.00055 C15 1 0.751054 0.239228 -0.021291 11.00000 0.04582 0.03517 = 0.04121 0.00552 0.02412 0.00410 AFIX 43 H15 2 0.738772 0.380857 -0.062239 11.00000 -1.20000 AFIX 0 C16 1 0.684482 0.182982 0.023291 11.00000 0.03944 0.03156 = 0.04330 0.00314 0.02301 0.00746 AFIX 43 H16 2 0.627210 0.289542 0.012959 11.00000 -1.20000 AFIX 0 C21 1 0.505725 0.064042 0.191311 11.00000 0.03300 0.02673 = 0.03410 -0.00380 0.01781 -0.00359 C22 1 0.428092 0.250954 0.166571 11.00000 0.04212 0.02987 = 0.04682 0.00292 0.02515 0.00200 AFIX 43 H22 2 0.429579 0.383564 0.125813 11.00000 -1.20000 AFIX 0 N23 3 0.351516 0.253127 0.197329 11.00000 0.04403 0.03972 = 0.06041 -0.00195 0.03206 0.00256 C24 1 0.351111 0.060182 0.255612 11.00000 0.04663 0.04460 = 0.05341 -0.00917 0.03330 -0.00917 AFIX 43 H24 2 0.297710 0.055623 0.277244 11.00000 -1.20000 AFIX 0 C25 1 0.425829 -0.132447 0.285300 11.00000 0.05434 0.03782 = 0.04434 0.00067 0.02954 -0.00875 AFIX 43 H25 2 0.422701 -0.261897 0.326535 11.00000 -1.20000 AFIX 0 C26 1 0.505514 -0.132135 0.253406 11.00000 0.04212 0.03216 = 0.03933 0.00277 0.01991 0.00010 AFIX 43 H26 2 0.557180 -0.259223 0.272962 11.00000 -1.20000 HKLF 4 REM 10-127 is Fpm in P21/n at RT with Mo at 40kV30mA to 0.75\%A [8-06] REM R1 = 0.0415 for 2338 Fo > 4sig(Fo) and 0.0463 for all 2624 data REM 150 parameters refined using 0 restraints END WGHT 0.0519 0.3065 REM Highest difference peak 0.251, deepest hole -0.191, 1-sigma level 0.035 Q1 1 0.6603 -0.0673 0.0994 11.00000 0.05 0.25 Q2 1 0.7390 -0.1052 0.0845 11.00000 0.05 0.23 Q3 1 0.7139 0.1032 0.0733 11.00000 0.05 0.22 Q4 1 0.7818 0.1177 -0.0238 11.00000 0.05 0.22 Q5 1 0.7370 0.2425 0.0256 11.00000 0.05 0.22 Q6 1 0.5377 0.0667 0.1686 11.00000 0.05 0.21 Q7 1 0.4565 0.1331 0.1692 11.00000 0.05 0.21 Q8 1 0.5001 -0.0462 0.2136 11.00000 0.05 0.20 Q9 1 0.8144 0.2059 0.0145 11.00000 0.05 0.20 Q10 1 0.8579 0.0141 0.0494 11.00000 0.05 0.20 ; _[local]_cod_data_source_file gp5047.cif _[local]_cod_data_source_block Fpm_O-10-127 _[local]_cod_cif_authors_sg_H-M 'P 21/n' _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_original_cell_volume 992.74(3) _cod_database_code 2105077 loop_ _symmetry_equiv_pos_as_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_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 F14 0.90021(7) 0.1346(2) -0.04677(7) 0.0661(3) Uani d . 1 1 O O1 0.61595(9) -0.33340(17) 0.14280(9) 0.0553(3) Uani d . 1 1 C C1 0.63029(9) -0.1073(2) 0.12902(8) 0.0334(2) Uani d . 1 1 N N1 0.58246(8) 0.08878(19) 0.15340(7) 0.0338(2) Uani d . 1 1 H H1 0.5976(12) 0.243(3) 0.1431(11) 0.044(4) Uiso d . 1 1 C C11 0.70251(8) -0.0311(2) 0.08326(8) 0.0308(2) Uani d . 1 1 C C12 0.78845(9) -0.1890(2) 0.09844(9) 0.0364(3) Uani d . 1 1 H H12 0.8002 -0.3341 0.1376 0.044 Uiso calc R 1 1 C C13 0.85672(10) -0.1329(3) 0.05593(10) 0.0427(3) Uani d . 1 1 H H13 0.9152 -0.2360 0.0671 0.051 Uiso calc R 1 1 C C14 0.83564(10) 0.0796(3) -0.00319(9) 0.0399(3) Uani d . 1 1 C C15 0.75105(10) 0.2392(2) -0.02129(9) 0.0387(3) Uani d . 1 1 H H15 0.7388 0.3809 -0.0622 0.046 Uiso calc R 1 1 C C16 0.68448(9) 0.1830(2) 0.02329(9) 0.0362(3) Uani d . 1 1 H H16 0.6272 0.2895 0.0130 0.043 Uiso calc R 1 1 C C21 0.50573(8) 0.0640(2) 0.19131(8) 0.0300(2) Uani d . 1 1 C C22 0.42809(10) 0.2510(2) 0.16657(9) 0.0374(3) Uani d . 1 1 H H22 0.4296 0.3836 0.1258 0.045 Uiso calc R 1 1 N N23 0.35152(9) 0.2531(2) 0.19733(9) 0.0446(3) Uani d . 1 1 C C24 0.35111(11) 0.0602(3) 0.25561(10) 0.0440(3) Uani d . 1 1 H H24 0.2977 0.0556 0.2772 0.053 Uiso calc R 1 1 C C25 0.42583(11) -0.1324(3) 0.28530(9) 0.0425(3) Uani d . 1 1 H H25 0.4227 -0.2619 0.3265 0.051 Uiso calc R 1 1 C C26 0.50551(10) -0.1321(2) 0.25341(9) 0.0369(3) Uani d . 1 1 H H26 0.5572 -0.2592 0.2730 0.044 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 F14 0.0582(5) 0.0835(7) 0.0797(6) 0.0152(5) 0.0514(5) 0.0249(5) O1 0.0769(7) 0.0246(4) 0.0917(8) 0.0005(4) 0.0621(6) 0.0012(5) C1 0.0372(5) 0.0267(5) 0.0407(6) 0.0001(4) 0.0208(5) -0.0003(4) N1 0.0399(5) 0.0240(4) 0.0467(5) -0.0006(4) 0.0273(4) 0.0011(4) C11 0.0333(5) 0.0279(5) 0.0340(5) 0.0005(4) 0.0169(4) -0.0023(4) C12 0.0362(6) 0.0342(6) 0.0394(6) 0.0063(4) 0.0167(5) 0.0049(5) C13 0.0345(6) 0.0466(7) 0.0500(7) 0.0111(5) 0.0207(5) 0.0053(6) C14 0.0369(6) 0.0483(7) 0.0418(6) 0.0005(5) 0.0238(5) 0.0013(5) C15 0.0458(6) 0.0352(6) 0.0412(6) 0.0041(5) 0.0241(5) 0.0055(5) C16 0.0394(6) 0.0316(6) 0.0433(6) 0.0075(4) 0.0230(5) 0.0031(5) C21 0.0330(5) 0.0267(5) 0.0341(5) -0.0036(4) 0.0178(4) -0.0038(4) C22 0.0421(6) 0.0299(5) 0.0468(6) 0.0020(5) 0.0252(5) 0.0029(5) N23 0.0440(6) 0.0397(6) 0.0604(7) 0.0026(5) 0.0321(5) -0.0020(5) C24 0.0466(7) 0.0446(7) 0.0534(7) -0.0092(5) 0.0333(6) -0.0092(6) C25 0.0543(7) 0.0378(6) 0.0443(6) -0.0088(5) 0.0295(6) 0.0007(5) C26 0.0421(6) 0.0322(6) 0.0393(6) 0.0001(5) 0.0199(5) 0.0028(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 122.98(11) O1 C1 C11 121.51(10) N1 C1 C11 115.50(10) C1 N1 C21 125.76(10) C1 N1 H1 117.9(10) C21 N1 H1 116.3(10) C16 C11 C12 119.29(10) C16 C11 C1 122.72(10) C12 C11 C1 117.93(10) C13 C12 C11 120.76(11) C13 C12 H12 119.6 C11 C12 H12 119.6 C14 C13 C12 118.01(11) C14 C13 H13 121.0 C12 C13 H13 121.0 F14 C14 C13 118.83(11) F14 C14 C15 117.91(12) C13 C14 C15 123.26(11) C14 C15 C16 118.03(11) C14 C15 H15 121.0 C16 C15 H15 121.0 C15 C16 C11 120.63(10) C15 C16 H16 119.7 C11 C16 H16 119.7 C22 C21 C26 118.45(10) C22 C21 N1 117.73(10) C26 C21 N1 123.80(10) N23 C22 C21 124.25(11) N23 C22 H22 117.9 C21 C22 H22 117.9 C22 N23 C24 116.64(11) N23 C24 C25 123.31(11) N23 C24 H24 118.3 C25 C24 H24 118.3 C24 C25 C26 119.61(11) C24 C25 H25 120.2 C26 C25 H25 120.2 C25 C26 C21 117.73(11) C25 C26 H26 121.1 C21 C26 H26 121.1 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F14 C14 1.3490(13) O1 C1 1.2259(14) C1 N1 1.3514(14) C1 C11 1.4933(15) N1 C21 1.4144(13) N1 H1 0.859(17) C11 C16 1.3894(16) C11 C12 1.3904(15) C12 C13 1.3835(17) C12 H12 0.9300 C13 C14 1.3725(19) C13 H13 0.9300 C14 C15 1.3729(17) C15 C16 1.3864(16) C15 H15 0.9300 C16 H16 0.9300 C21 C22 1.3848(16) C21 C26 1.3859(16) C22 N23 1.3305(15) C22 H22 0.9300 N23 C24 1.3358(18) C24 C25 1.378(2) C24 H24 0.9300 C25 C26 1.3833(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 O1 1_565 0.859(17) 2.221(17) 3.0575(13) 164.6(14) yes C26 H26 O1 . 0.93 2.45 2.8987(15) 109 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 -4.3(2) C11 C1 N1 C21 175.46(10) O1 C1 C11 C16 146.70(13) N1 C1 C11 C16 -33.10(16) O1 C1 C11 C12 -30.39(17) N1 C1 C11 C12 149.82(11) C16 C11 C12 C13 1.08(18) C1 C11 C12 C13 178.27(11) C11 C12 C13 C14 -1.42(19) C12 C13 C14 F14 -178.74(12) C12 C13 C14 C15 0.6(2) F14 C14 C15 C16 179.91(11) C13 C14 C15 C16 0.6(2) C14 C15 C16 C11 -0.93(19) C12 C11 C16 C15 0.12(18) C1 C11 C16 C15 -176.93(11) C1 N1 C21 C22 -147.25(12) C1 N1 C21 C26 34.42(18) C26 C21 C22 N23 -1.13(18) N1 C21 C22 N23 -179.55(11) C21 C22 N23 C24 -0.13(19) C22 N23 C24 C25 1.1(2) N23 C24 C25 C26 -0.7(2) C24 C25 C26 C21 -0.61(18) C22 C21 C26 C25 1.45(17) N1 C21 C26 C25 179.76(11)