#------------------------------------------------------------------------------ #$Date: 2014-10-25 18:23:10 +0100 (Sat, 25 Oct 2014) $ #$Revision: 125873 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/50/2105081.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_2105081 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_name_common Fom_F _chemical_name_systematic 2-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 92.150(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.4788(2) _cell_length_b 8.8223(4) _cell_length_c 20.4414(7) _cell_measurement_reflns_used 1933 _cell_measurement_temperature 294.0(10) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 2.55 _cell_volume 987.35(7) _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 0.936 _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 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 7439 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 27.75 _diffrn_reflns_theta_min 2.51 _diffrn_standards_decay_% 1 _diffrn_standards_interval_time 60 _diffrn_standards_number 7692 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_T_max 0.9871 _exptl_absorpt_correction_T_min 0.9489 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(ABSFAC, Clark and Reid, 1998)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 448 _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.142 _refine_diff_density_min -0.179 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 149 _refine_ls_number_reflns 2178 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all 0.0630 _refine_ls_R_factor_gt 0.0437 _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^)+(0.0574P)^2^+0.0509P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1095 _refine_ls_wR_factor_ref 0.1217 _reflns_number_gt 1599 _reflns_number_total 2178 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL 11-061 is Fom in P21/n at RT with Mo 45kV35mA to 0.80\%A [MeOH/Et2O] CELL 0.71073 5.4788 8.8223 20.4414 90.000 92.150 90.000 ZERR 4 0.0002 0.0004 0.0007 0.000 0.004 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 $1 1+X,Y,Z EQIV $2 1/2+X,1/2-Y,1/2+Z HTAB N1 F12 HTAB C16 O1 HTAB C22 O1 HTAB N1 O1_$1 HTAB C14 N23_$2 RTAB FC F12 C12 RTAB CC C1 C11 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 CNC C22 N23 C24 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 CCN C24 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 0.12 0.25 0.49 TEMP 21 PLAN 10 MPLA 6 C11 C12 C13 C14 C15 C16 F12 MPLA 3 O1 N1 C1 C11 C21 F12 MPLA 6 C21 C22 N23 C24 C25 C26 F12 MPLA 6 C11 C12 C13 C14 C15 C16 F12 MPLA 5 O1 N1 C1 C11 C21 MPLA 6 C21 C22 N23 C24 C25 C26 WGHT 0.057400 0.050900 FVAR 8.33990 MOLE 1 F12 5 0.299999 0.142118 0.031757 11.00000 0.05751 0.07600 = 0.06128 -0.00054 -0.01111 0.01821 O1 4 -0.326350 0.196444 -0.085721 11.00000 0.04666 0.07133 = 0.06174 -0.01250 -0.01355 0.00415 C1 1 -0.120903 0.195347 -0.060456 11.00000 0.04803 0.03902 = 0.05120 0.00145 -0.00650 -0.00162 N1 3 0.073717 0.133101 -0.089547 11.00000 0.04415 0.05410 = 0.05193 -0.00823 -0.00904 0.00229 H1 2 0.208395 0.137423 -0.067615 11.00000 0.05807 C11 1 -0.071298 0.269215 0.004979 11.00000 0.04411 0.03802 = 0.04556 0.00367 -0.00504 -0.00450 C12 1 0.127466 0.246214 0.047183 11.00000 0.04361 0.04816 = 0.04982 0.00729 -0.00013 0.00016 C13 1 0.162000 0.322629 0.105335 11.00000 0.05216 0.06617 = 0.04517 0.00574 -0.00913 -0.00589 AFIX 43 H13 2 0.299569 0.304210 0.132195 11.00000 -1.20000 AFIX 0 C14 1 -0.009592 0.426603 0.123217 11.00000 0.06277 0.06102 = 0.04688 -0.00624 -0.00164 -0.00794 AFIX 43 H14 2 0.012176 0.480511 0.162096 11.00000 -1.20000 AFIX 0 C15 1 -0.213634 0.450690 0.083432 11.00000 0.05865 0.05438 = 0.05902 -0.00756 -0.00195 0.00280 AFIX 43 H15 2 -0.331977 0.519494 0.095784 11.00000 -1.20000 AFIX 0 C16 1 -0.242740 0.373037 0.025368 11.00000 0.04837 0.05015 = 0.05614 -0.00158 -0.00974 0.00100 AFIX 43 H16 2 -0.381690 0.390649 -0.001070 11.00000 -1.20000 AFIX 0 C21 1 0.072537 0.049880 -0.148499 11.00000 0.04697 0.04410 = 0.04314 0.00177 -0.00280 -0.00421 C22 1 -0.112752 0.055280 -0.196184 11.00000 0.05866 0.08256 = 0.05072 -0.00324 -0.00839 0.01640 AFIX 43 H22 2 -0.244347 0.119597 -0.189953 11.00000 -1.20000 AFIX 0 N23 3 -0.111458 -0.027965 -0.251015 11.00000 0.06311 0.10600 = 0.04824 -0.00735 -0.01025 0.00592 C24 1 0.078926 -0.116150 -0.259897 11.00000 0.06381 0.06991 = 0.04880 -0.00787 0.00595 -0.01171 AFIX 43 H24 2 0.081196 -0.174334 -0.297807 11.00000 -1.20000 AFIX 0 C25 1 0.273029 -0.126187 -0.216103 11.00000 0.05969 0.06620 = 0.05966 -0.00979 0.00060 0.00730 AFIX 43 H25 2 0.405206 -0.188522 -0.224407 11.00000 -1.20000 AFIX 0 C26 1 0.268653 -0.042260 -0.159592 11.00000 0.05034 0.06206 = 0.05531 -0.00536 -0.01049 0.00538 AFIX 43 H26 2 0.398107 -0.047809 -0.128931 11.00000 -1.20000 HKLF 4 REM 11-061 is Fom in P21/n at RT with Mo 45kV35mA to 0.80\%A [MeOH/Et2O] REM R1 = 0.0437 for 1599 Fo > 4sig(Fo) and 0.0630 for all 2178 data REM 149 parameters refined using 0 restraints END WGHT 0.0574 0.0509 REM Highest difference peak 0.142, deepest hole -0.179, 1-sigma level 0.032 Q1 1 0.0632 0.2921 0.0114 11.00000 0.05 0.14 Q2 1 -0.1018 0.2220 -0.0232 11.00000 0.05 0.14 Q3 1 -0.0473 0.0187 -0.1612 11.00000 0.05 0.13 Q4 1 0.1456 -0.1620 -0.2154 11.00000 0.05 0.12 Q5 1 -0.0843 0.0549 -0.2458 11.00000 0.05 0.12 Q6 1 -0.2044 0.0095 -0.2863 11.00000 0.05 0.11 Q7 1 -0.2692 0.1379 -0.0618 11.00000 0.05 0.11 Q8 1 0.3517 -0.1007 -0.1188 11.00000 0.05 0.11 Q9 1 -0.0203 0.2311 0.0298 11.00000 0.05 0.11 Q10 1 0.4490 0.0017 -0.1375 11.00000 0.05 0.10 ; _[local]_cod_data_source_file gp5047.cif _[local]_cod_data_source_block Fom_F-11-061 _[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 2105081 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 F12 0.30000(17) 0.14212(11) 0.03176(4) 0.0653(3) Uani d . 1 1 O O1 -0.32635(19) 0.19644(13) -0.08572(5) 0.0603(3) Uani d . 1 1 C C1 -0.1209(3) 0.19535(16) -0.06046(7) 0.0463(4) Uani d . 1 1 N N1 0.0737(3) 0.13310(14) -0.08955(7) 0.0503(4) Uani d . 1 1 H H1 0.208(3) 0.1374(18) -0.0676(8) 0.058(5) Uiso d . 1 1 C C11 -0.0713(3) 0.26922(15) 0.00498(7) 0.0427(3) Uani d . 1 1 C C12 0.1275(3) 0.24621(17) 0.04718(7) 0.0472(4) Uani d . 1 1 C C13 0.1620(3) 0.32263(19) 0.10533(8) 0.0548(4) Uani d . 1 1 H H13 0.2996 0.3042 0.1322 0.066 Uiso calc R 1 1 C C14 -0.0096(3) 0.4266(2) 0.12322(8) 0.0570(4) Uani d . 1 1 H H14 0.0122 0.4805 0.1621 0.068 Uiso calc R 1 1 C C15 -0.2136(3) 0.45069(18) 0.08343(8) 0.0575(4) Uani d . 1 1 H H15 -0.3320 0.5195 0.0958 0.069 Uiso calc R 1 1 C C16 -0.2427(3) 0.37304(17) 0.02537(8) 0.0518(4) Uani d . 1 1 H H16 -0.3817 0.3906 -0.0011 0.062 Uiso calc R 1 1 C C21 0.0725(3) 0.04988(16) -0.14850(7) 0.0448(4) Uani d . 1 1 C C22 -0.1128(3) 0.0553(2) -0.19618(8) 0.0642(5) Uani d . 1 1 H H22 -0.2443 0.1196 -0.1900 0.077 Uiso calc R 1 1 N N23 -0.1115(3) -0.0280(2) -0.25101(7) 0.0728(5) Uani d . 1 1 C C24 0.0789(3) -0.1161(2) -0.25990(8) 0.0607(5) Uani d . 1 1 H H24 0.0812 -0.1743 -0.2978 0.073 Uiso calc R 1 1 C C25 0.2730(3) -0.1262(2) -0.21610(9) 0.0619(5) Uani d . 1 1 H H25 0.4052 -0.1885 -0.2244 0.074 Uiso calc R 1 1 C C26 0.2687(3) -0.04226(18) -0.15959(8) 0.0562(4) Uani d . 1 1 H H26 0.3981 -0.0478 -0.1289 0.067 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 F12 0.0575(6) 0.0760(7) 0.0613(6) 0.0182(5) -0.0111(5) -0.0005(5) O1 0.0467(7) 0.0713(8) 0.0617(7) 0.0041(5) -0.0136(5) -0.0125(6) C1 0.0480(9) 0.0390(8) 0.0512(9) -0.0016(6) -0.0065(7) 0.0014(6) N1 0.0441(8) 0.0541(8) 0.0519(8) 0.0023(6) -0.0090(6) -0.0082(6) C11 0.0441(8) 0.0380(7) 0.0456(8) -0.0045(6) -0.0050(6) 0.0037(6) C12 0.0436(8) 0.0482(8) 0.0498(9) 0.0002(6) -0.0001(7) 0.0073(7) C13 0.0522(9) 0.0662(10) 0.0452(9) -0.0059(8) -0.0091(7) 0.0057(8) C14 0.0628(11) 0.0610(10) 0.0469(9) -0.0079(8) -0.0016(8) -0.0062(7) C15 0.0586(10) 0.0544(10) 0.0590(10) 0.0028(8) -0.0020(8) -0.0076(8) C16 0.0484(9) 0.0502(9) 0.0561(10) 0.0010(7) -0.0097(7) -0.0016(7) C21 0.0470(8) 0.0441(8) 0.0431(8) -0.0042(6) -0.0028(6) 0.0018(6) C22 0.0587(10) 0.0826(13) 0.0507(10) 0.0164(9) -0.0084(8) -0.0032(9) N23 0.0631(10) 0.1060(13) 0.0482(8) 0.0059(9) -0.0103(7) -0.0074(8) C24 0.0638(11) 0.0699(11) 0.0488(10) -0.0117(9) 0.0060(8) -0.0079(8) C25 0.0597(11) 0.0662(11) 0.0597(11) 0.0073(8) 0.0006(9) -0.0098(8) C26 0.0503(10) 0.0621(10) 0.0553(10) 0.0054(8) -0.0105(8) -0.0054(8) 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 123.05(14) O1 C1 C11 120.40(14) N1 C1 C11 116.53(13) C1 N1 C21 127.35(14) C1 N1 H1 115.6(12) C21 N1 H1 116.7(12) C12 C11 C16 115.91(14) C12 C11 C1 127.23(14) C16 C11 C1 116.85(13) F12 C12 C13 117.17(13) F12 C12 C11 119.51(13) C13 C12 C11 123.31(15) C14 C13 C12 119.01(15) C14 C13 H13 120.5 C12 C13 H13 120.5 C13 C14 C15 119.72(15) C13 C14 H14 120.1 C15 C14 H14 120.1 C14 C15 C16 119.96(16) C14 C15 H15 120.0 C16 C15 H15 120.0 C15 C16 C11 122.05(15) C15 C16 H16 119.0 C11 C16 H16 119.0 C26 C21 C22 117.57(14) C26 C21 N1 118.07(13) C22 C21 N1 124.36(14) N23 C22 C21 122.98(16) N23 C22 H22 118.5 C21 C22 H22 118.5 C24 N23 C22 117.86(15) N23 C24 C25 123.21(16) N23 C24 H24 118.4 C25 C24 H24 118.4 C24 C25 C26 118.57(16) C24 C25 H25 120.7 C26 C25 H25 120.7 C21 C26 C25 119.78(15) C21 C26 H26 120.1 C25 C26 H26 120.1 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F12 C12 1.3634(17) O1 C1 1.2207(17) C1 N1 1.356(2) C1 C11 1.5035(19) N1 C21 1.4109(19) N1 H1 0.850(17) C11 C12 1.3787(19) C11 C16 1.387(2) C12 C13 1.373(2) C13 C14 1.373(2) C13 H13 0.9300 C14 C15 1.374(2) C14 H14 0.9300 C15 C16 1.375(2) C15 H15 0.9300 C16 H16 0.9300 C21 C26 1.373(2) C21 C22 1.382(2) C22 N23 1.340(2) C22 H22 0.9300 N23 C24 1.319(2) C24 C25 1.367(2) C24 H24 0.9300 C25 C26 1.373(2) 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_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 F12 0.850(17) 2.074(17) 2.7315(16) 133.7(15) yes C16 H16 O1 0.93 2.46 2.7777(19) 100 yes C22 H22 O1 0.93 2.30 2.867(2) 119 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 -6.1(2) C11 C1 N1 C21 175.78(12) O1 C1 C11 C12 162.20(15) N1 C1 C11 C12 -19.6(2) O1 C1 C11 C16 -18.3(2) N1 C1 C11 C16 159.90(13) C16 C11 C12 F12 177.76(13) C1 C11 C12 F12 -2.7(2) C16 C11 C12 C13 -1.7(2) C1 C11 C12 C13 177.81(14) F12 C12 C13 C14 -178.93(14) C11 C12 C13 C14 0.5(2) C12 C13 C14 C15 1.0(2) C13 C14 C15 C16 -1.3(3) C14 C15 C16 C11 0.1(3) C12 C11 C16 C15 1.4(2) C1 C11 C16 C15 -178.19(13) C1 N1 C21 C26 -160.11(15) C1 N1 C21 C22 20.2(2) C26 C21 C22 N23 2.0(3) N1 C21 C22 N23 -178.34(16) C21 C22 N23 C24 -1.5(3) C22 N23 C24 C25 0.0(3) N23 C24 C25 C26 1.0(3) C22 C21 C26 C25 -0.9(2) N1 C21 C26 C25 179.36(14) C24 C25 C26 C21 -0.5(3) _cod_database_fobs_code 2105081 _journal_paper_doi 10.1107/S0108768112006799