#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/50/2105078.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_2105078 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 423 _chemical_name_common Fpm_N _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 95.181(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 3.9077(2) _cell_length_b 24.2444(12) _cell_length_c 10.7012(5) _cell_measurement_reflns_used 1505 _cell_measurement_temperature 294.0(10) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 2.55 _cell_volume 1009.69(9) _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 0.999 _diffrn_measured_fraction_theta_max 0.949 _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 0.0488 _diffrn_reflns_av_sigmaI/netI 0.0724 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 6537 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 27.36 _diffrn_reflns_theta_min 2.09 _diffrn_standards_decay_% 1 _diffrn_standards_interval_time 60 _diffrn_standards_number 6646 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_T_max 0.9968 _exptl_absorpt_correction_T_min 0.9751 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(ABSFAC, Clark and Reid, 1998)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 448 _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.162 _refine_diff_density_min -0.162 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.960 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 149 _refine_ls_number_reflns 2162 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.960 _refine_ls_R_factor_all 0.1120 _refine_ls_R_factor_gt 0.0527 _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^)+(0.027P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0944 _refine_ls_wR_factor_ref 0.1199 _reflns_number_gt 1154 _reflns_number_total 2162 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL 10-121 is Fpm in P21/n at RT with Mo at 45kV35mA to 0.80\%A [8-06] CELL 0.71073 3.9077 24.2444 10.7012 90.000 95.181 90.000 ZERR 4 0.0002 0.0012 0.0005 0.000 0.005 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 3 LIST 4 ACTA 52 CONF BOND $H HTAB EQIV $2 -1/2+X,1/2-Y,-1/2+Z HTAB N1 N23_$2 HTAB C16 N23_$2 HTAB C22 O1 HTAB C26 N23_$2 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 0.03 0.05 0.24 TEMP 21 PLAN 10 MPLA 6 C11 C12 C13 C14 C15 C16 F14 MPLA 5 O1 N1 C1 C11 C21 F14 MPLA 6 C21 C22 N23 C24 C25 C26 F14 MPLA 6 C11 C12 C13 C14 C15 C16 F14 MPLA 3 O1 N1 C1 C11 C21 F14 MPLA 6 C21 C22 N23 C24 C25 C26 F14 WGHT 0.027000 FVAR 7.35416 MOLE 1 F14 5 0.290578 -0.046640 0.144089 11.00000 0.15405 0.05887 = 0.07750 -0.01251 -0.00415 -0.02955 O1 4 0.908618 0.138397 0.504431 11.00000 0.13395 0.07089 = 0.03278 0.00533 -0.01111 -0.02072 C1 1 0.839841 0.140484 0.390514 11.00000 0.06754 0.05034 = 0.03435 0.00201 0.00045 0.00181 N1 3 0.908307 0.185775 0.322025 11.00000 0.07128 0.04668 = 0.02752 -0.00170 -0.00294 -0.00115 H1 2 0.855850 0.185355 0.243992 11.00000 0.06503 C11 1 0.686128 0.092288 0.320274 11.00000 0.05875 0.04422 = 0.03447 0.00305 0.00275 -0.00050 C12 1 0.718172 0.041478 0.378002 11.00000 0.08553 0.05174 = 0.04318 0.00814 -0.00547 -0.00235 AFIX 43 H12 2 0.828414 0.039068 0.458550 11.00000 -1.20000 AFIX 0 C13 1 0.591864 -0.005525 0.319794 11.00000 0.10267 0.04831 = 0.05885 0.00831 0.00202 -0.00027 AFIX 43 H13 2 0.620165 -0.039713 0.358773 11.00000 -1.20000 AFIX 0 C14 1 0.422683 -0.000752 0.202545 11.00000 0.09158 0.04852 = 0.05100 -0.00805 0.00580 -0.01288 C15 1 0.380922 0.048430 0.142372 11.00000 0.07619 0.05569 = 0.04196 -0.00304 -0.00277 -0.00720 AFIX 43 H15 2 0.265333 0.050463 0.062637 11.00000 -1.20000 AFIX 0 C16 1 0.512724 0.095185 0.201522 11.00000 0.06421 0.04511 = 0.03993 0.00540 0.00052 0.00091 AFIX 43 H16 2 0.485241 0.129135 0.161416 11.00000 -1.20000 AFIX 0 C21 1 1.063115 0.235324 0.365441 11.00000 0.05481 0.04447 = 0.03076 -0.00229 -0.00120 0.00526 C22 1 1.129734 0.249146 0.491424 11.00000 0.07978 0.05135 = 0.02719 -0.00029 -0.00039 0.00118 AFIX 43 H22 2 1.072123 0.223934 0.551580 11.00000 -1.20000 AFIX 0 N23 3 1.272422 0.296887 0.529978 11.00000 0.09420 0.04713 = 0.03461 -0.00554 -0.00766 0.00079 C24 1 1.352992 0.332740 0.443743 11.00000 0.08701 0.04642 = 0.04382 -0.00408 -0.01230 -0.00008 AFIX 43 H24 2 1.449029 0.366331 0.470178 11.00000 -1.20000 AFIX 0 C25 1 1.301157 0.322555 0.317224 11.00000 0.07936 0.04759 = 0.03802 0.00142 -0.00345 -0.00462 AFIX 43 H25 2 1.364547 0.348366 0.259300 11.00000 -1.20000 AFIX 0 C26 1 1.154093 0.273554 0.278383 11.00000 0.07117 0.05110 = 0.02933 -0.00017 -0.00289 0.00177 AFIX 43 H26 2 1.115134 0.265915 0.193120 11.00000 -1.20000 HKLF 4 REM 10-121 is Fpm in P21/n at RT with Mo at 45kV35mA to 0.80\%A [8-06] REM R1 = 0.0527 for 1154 Fo > 4sig(Fo) and 0.1120 for all 2162 data REM 149 parameters refined using 0 restraints END WGHT 0.0270 0.0000 REM Highest difference peak 0.162, deepest hole -0.162, 1-sigma level 0.035 Q1 1 1.0808 0.1348 0.4647 11.00000 0.05 0.16 Q2 1 0.5265 -0.0650 0.1579 11.00000 0.05 0.15 Q3 1 0.2874 0.1293 0.2015 11.00000 0.05 0.14 Q4 1 1.5138 0.2490 0.4887 11.00000 0.05 0.13 Q5 1 1.2168 0.1814 0.3249 11.00000 0.05 0.12 Q6 1 1.2542 0.1605 0.5164 11.00000 0.05 0.11 Q7 1 1.1289 0.2408 0.4241 11.00000 0.05 0.11 Q8 1 0.4744 0.1720 0.0753 11.00000 0.05 0.11 Q9 1 1.5637 0.2524 0.3033 11.00000 0.05 0.11 Q10 1 0.3651 0.1060 -0.0215 11.00000 0.05 0.11 ; _[local]_cod_data_source_file gp5047.cif _[local]_cod_data_source_block Fpm_N-10-121 _[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_database_code 2105078 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 0.2906(5) -0.04664(7) 0.14409(16) 0.0977(6) Uani d . 1 1 O O1 0.9086(5) 0.13840(8) 0.50443(16) 0.0803(6) Uani d . 1 1 C C1 0.8398(6) 0.14048(10) 0.3905(2) 0.0510(6) Uani d . 1 1 N N1 0.9083(5) 0.18577(8) 0.3220(2) 0.0489(5) Uani d . 1 1 H H1 0.856(6) 0.1854(10) 0.244(3) 0.065(8) Uiso d . 1 1 C C11 0.6861(6) 0.09229(9) 0.3203(2) 0.0459(6) Uani d . 1 1 C C12 0.7182(7) 0.04148(10) 0.3780(2) 0.0608(7) Uani d . 1 1 H H12 0.8284 0.0391 0.4586 0.073 Uiso calc R 1 1 C C13 0.5919(7) -0.00553(11) 0.3198(3) 0.0703(8) Uani d . 1 1 H H13 0.6202 -0.0397 0.3588 0.084 Uiso calc R 1 1 C C14 0.4227(7) -0.00075(11) 0.2025(3) 0.0637(7) Uani d . 1 1 C C15 0.3809(6) 0.04843(11) 0.1424(2) 0.0584(7) Uani d . 1 1 H H15 0.2653 0.0505 0.0626 0.070 Uiso calc R 1 1 C C16 0.5127(6) 0.09519(10) 0.2015(2) 0.0500(6) Uani d . 1 1 H H16 0.4852 0.1291 0.1614 0.060 Uiso calc R 1 1 C C21 1.0631(5) 0.23532(9) 0.3654(2) 0.0437(6) Uani d . 1 1 C C22 1.1297(6) 0.24915(10) 0.4914(2) 0.0531(6) Uani d . 1 1 H H22 1.0721 0.2239 0.5516 0.064 Uiso calc R 1 1 N N23 1.2724(6) 0.29689(8) 0.52998(18) 0.0595(6) Uani d . 1 1 C C24 1.3530(7) 0.33274(10) 0.4437(2) 0.0602(7) Uani d . 1 1 H H24 1.4490 0.3663 0.4702 0.072 Uiso calc R 1 1 C C25 1.3012(6) 0.32256(10) 0.3172(2) 0.0555(7) Uani d . 1 1 H H25 1.3645 0.3484 0.2593 0.067 Uiso calc R 1 1 C C26 1.1541(6) 0.27355(10) 0.2784(2) 0.0510(6) Uani d . 1 1 H H26 1.1151 0.2659 0.1931 0.061 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 0.1541(16) 0.0589(10) 0.0775(13) -0.0296(11) -0.0042(11) -0.0125(9) O1 0.1340(17) 0.0709(13) 0.0328(11) -0.0207(12) -0.0111(10) 0.0053(9) C1 0.0675(16) 0.0503(15) 0.0344(14) 0.0018(13) 0.0004(12) 0.0020(11) N1 0.0713(14) 0.0467(12) 0.0275(11) -0.0011(11) -0.0029(10) -0.0017(9) C11 0.0587(14) 0.0442(13) 0.0345(13) -0.0005(12) 0.0027(11) 0.0031(11) C12 0.0855(19) 0.0517(16) 0.0432(15) -0.0023(14) -0.0055(13) 0.0081(12) C13 0.103(2) 0.0483(17) 0.0588(19) -0.0003(15) 0.0020(16) 0.0083(14) C14 0.092(2) 0.0485(16) 0.0510(17) -0.0129(14) 0.0058(15) -0.0081(13) C15 0.0762(17) 0.0557(16) 0.0420(15) -0.0072(14) -0.0028(12) -0.0030(12) C16 0.0642(15) 0.0451(14) 0.0399(14) 0.0009(12) 0.0005(11) 0.0054(11) C21 0.0548(14) 0.0445(13) 0.0308(12) 0.0053(11) -0.0012(10) -0.0023(10) C22 0.0798(18) 0.0513(15) 0.0272(12) 0.0012(13) -0.0004(11) -0.0003(11) N23 0.0942(16) 0.0471(12) 0.0346(12) 0.0008(12) -0.0077(11) -0.0055(10) C24 0.0870(19) 0.0464(14) 0.0438(16) -0.0001(14) -0.0123(13) -0.0041(12) C25 0.0794(17) 0.0476(15) 0.0380(14) -0.0046(13) -0.0035(12) 0.0014(11) C26 0.0712(16) 0.0511(15) 0.0293(13) 0.0018(13) -0.0029(11) -0.0002(11) 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 122.2(2) O1 C1 C11 120.9(2) N1 C1 C11 116.9(2) C1 N1 C21 127.7(2) C1 N1 H1 118.9(18) C21 N1 H1 113.4(18) C12 C11 C16 118.2(2) C12 C11 C1 117.4(2) C16 C11 C1 124.4(2) C13 C12 C11 121.7(2) C13 C12 H12 119.2 C11 C12 H12 119.2 C12 C13 C14 118.1(2) C12 C13 H13 121.0 C14 C13 H13 121.0 F14 C14 C15 118.5(2) F14 C14 C13 119.1(2) C15 C14 C13 122.4(2) C14 C15 C16 118.8(2) C14 C15 H15 120.6 C16 C15 H15 120.6 C15 C16 C11 120.8(2) C15 C16 H16 119.6 C11 C16 H16 119.6 C26 C21 C22 117.0(2) C26 C21 N1 118.6(2) C22 C21 N1 124.3(2) N23 C22 C21 123.0(2) N23 C22 H22 118.5 C21 C22 H22 118.5 C24 N23 C22 118.2(2) N23 C24 C25 123.0(2) N23 C24 H24 118.5 C25 C24 H24 118.5 C26 C25 C24 118.4(2) C26 C25 H25 120.8 C24 C25 H25 120.8 C25 C26 C21 120.3(2) C25 C26 H26 119.9 C21 C26 H26 119.9 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F14 C14 1.355(3) O1 C1 1.225(3) C1 N1 1.360(3) C1 C11 1.486(3) N1 C21 1.405(3) N1 H1 0.84(3) C11 C12 1.379(3) C11 C16 1.387(3) C12 C13 1.369(3) C12 H12 0.9300 C13 C14 1.369(4) C13 H13 0.9300 C14 C15 1.358(3) C15 C16 1.375(3) C15 H15 0.9300 C16 H16 0.9300 C21 C26 1.383(3) C21 C22 1.391(3) C22 N23 1.334(3) C22 H22 0.9300 N23 C24 1.326(3) C24 C25 1.373(3) C24 H24 0.9300 C25 C26 1.368(3) 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 N23 4_565 0.84(3) 2.32(3) 3.151(3) 167(2) yes C22 H22 O1 . 0.93 2.21 2.828(3) 123 yes C16 H16 N23 4_565 0.93 2.60 3.404(3) 146 yes C26 H26 N23 4_565 0.93 2.60 3.390(3) 144 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 0.6(4) C11 C1 N1 C21 -177.6(2) O1 C1 C11 C12 -18.9(3) N1 C1 C11 C12 159.2(2) O1 C1 C11 C16 160.8(2) N1 C1 C11 C16 -21.0(3) C16 C11 C12 C13 1.7(4) C1 C11 C12 C13 -178.5(2) C11 C12 C13 C14 -1.7(4) C12 C13 C14 F14 -178.9(2) C12 C13 C14 C15 0.9(4) F14 C14 C15 C16 179.6(2) C13 C14 C15 C16 -0.2(4) C14 C15 C16 C11 0.2(4) C12 C11 C16 C15 -0.9(3) C1 C11 C16 C15 179.3(2) C1 N1 C21 C26 171.0(2) C1 N1 C21 C22 -9.6(4) C26 C21 C22 N23 0.4(3) N1 C21 C22 N23 -179.0(2) C21 C22 N23 C24 0.2(4) C22 N23 C24 C25 -1.0(4) N23 C24 C25 C26 1.2(4) C24 C25 C26 C21 -0.5(4) C22 C21 C26 C25 -0.3(3) N1 C21 C26 C25 179.1(2) _cod_database_fobs_code 2105078