#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:53:41 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176768 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/50/2105074.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_2105074 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_paper_doi 10.1107/S0108768112006799 _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 461 _chemical_name_common Fpp _chemical_name_systematic 4-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 95.974(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.67770(10) _cell_length_b 11.4769(2) _cell_length_c 15.5289(3) _cell_measurement_reflns_used 5255 _cell_measurement_temperature 294.0(10) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 2.55 _cell_volume 1006.40(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 0.999 _diffrn_measured_fraction_theta_max 0.930 _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 0.0126 _diffrn_reflns_av_sigmaI/netI 0.0126 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 7351 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 27.77 _diffrn_reflns_theta_min 2.64 _diffrn_standards_decay_% 1 _diffrn_standards_interval_time 60 _diffrn_standards_number 7599 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_T_max 0.9801 _exptl_absorpt_correction_T_min 0.9598 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(ABSFAC, Clark and Reid, 1998)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 448 _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.19 _refine_diff_density_max 0.204 _refine_diff_density_min -0.135 _refine_ls_extinction_coef 0.029(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 1.043 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 150 _refine_ls_number_reflns 2216 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0337 _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^)+(0.0388P)^2^+0.2424P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0863 _refine_ls_wR_factor_ref 0.0898 _reflns_number_gt 1979 _reflns_number_total 2216 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL 10-124 is Fpp in P21/c at RT with Mo at 40kV30mA to 0.80\%A CELL 0.71073 5.6777 11.4769 15.5289 90.000 95.974 90.000 ZERR 4 0.0001 0.0002 0.0003 0.000 0.002 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 52 CONF BOND $H HTAB EQIV $2 1-X,1/2+Y,1/2-Z EQIV $3 2-X,-Y,1-Z EQIV $4 X,1/2-Y,1/2+Z HTAB N1 N24_$2 HTAB C26 O1 HTAB C26 C11_$3 HTAB C26 C12_$3 HTAB C26 C13_$3 HTAB C26 C14_$3 HTAB C26 C15_$3 HTAB C26 C16_$3 RTAB FC F14 C21_$4 RTAB FC F14 C22_$4 RTAB FC F14 C23_$4 RTAB FC F14 N24_$4 RTAB FC F14 C25_$4 RTAB FC F14 C26_$4 RTAB FC F14 C14 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 0.25 0.39 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 0.038800 0.242400 EXTI 0.028928 FVAR 8.97935 MOLE 1 F14 5 0.872295 0.459541 0.643582 11.00000 0.08558 0.06584 = 0.07536 -0.03978 0.00976 0.00754 O1 4 1.094790 0.049127 0.400121 11.00000 0.04049 0.04419 = 0.05905 -0.01365 0.00935 0.00311 C1 1 0.902283 0.090652 0.410830 11.00000 0.03996 0.03087 = 0.03128 0.00101 0.00308 0.00399 N1 3 0.692754 0.052571 0.369410 11.00000 0.04063 0.03930 = 0.04171 -0.01056 -0.00491 0.01143 H1 2 0.579508 0.100867 0.368242 11.00000 0.05632 C11 1 0.882000 0.190201 0.471516 11.00000 0.03658 0.03273 = 0.02826 0.00108 -0.00178 0.00706 C12 1 1.066704 0.269800 0.481035 11.00000 0.03925 0.03738 = 0.03540 0.00105 0.00314 0.00462 AFIX 43 H12 2 1.194465 0.261225 0.448640 11.00000 -1.20000 AFIX 0 C13 1 1.062293 0.361646 0.538233 11.00000 0.04692 0.03602 = 0.04784 -0.00356 -0.00236 0.00088 AFIX 43 H13 2 1.184117 0.416147 0.544151 11.00000 -1.20000 AFIX 0 C14 1 0.873087 0.370265 0.586114 11.00000 0.05546 0.04270 = 0.04147 -0.01267 -0.00222 0.01344 C15 1 0.688774 0.292867 0.579280 11.00000 0.04335 0.05727 = 0.04291 -0.00740 0.00733 0.01334 AFIX 43 H15 2 0.564081 0.301085 0.613184 11.00000 -1.20000 AFIX 0 C16 1 0.692129 0.202107 0.520788 11.00000 0.03676 0.04335 = 0.03922 -0.00169 0.00136 0.00437 AFIX 43 H16 2 0.567649 0.149097 0.514390 11.00000 -1.20000 AFIX 0 C21 1 0.658848 -0.040893 0.311687 11.00000 0.03944 0.03304 = 0.02987 -0.00112 0.00403 0.00053 C22 1 0.445261 -0.048437 0.259493 11.00000 0.03557 0.04392 = 0.04662 -0.00727 0.00312 0.00390 AFIX 43 H22 2 0.328512 0.007693 0.263008 11.00000 -1.20000 AFIX 0 C23 1 0.408905 -0.139840 0.202681 11.00000 0.03744 0.05307 = 0.04869 -0.01135 -0.00120 -0.00339 AFIX 43 H23 2 0.265362 -0.142944 0.167948 11.00000 -1.20000 AFIX 0 N24 3 0.566085 -0.224824 0.193882 11.00000 0.04570 0.04240 = 0.04544 -0.01126 0.00477 -0.00463 C25 1 0.768325 -0.216525 0.245392 11.00000 0.04570 0.03366 = 0.04361 -0.00346 0.00569 0.00300 AFIX 43 H25 2 0.880597 -0.274694 0.241202 11.00000 -1.20000 AFIX 0 C26 1 0.824109 -0.128589 0.304328 11.00000 0.04101 0.03522 = 0.03615 -0.00063 -0.00138 0.00426 AFIX 43 H26 2 0.968903 -0.127940 0.338371 11.00000 -1.20000 HKLF 4 REM 10-124 is Fpp in P21/c at RT with Mo at 40kV30mA to 0.80\%A REM R1 = 0.0337 for 1979 Fo > 4sig(Fo) and 0.0382 for all 2216 data REM 150 parameters refined using 0 restraints END WGHT 0.0388 0.2424 REM Highest difference peak 0.204, deepest hole -0.135, 1-sigma level 0.029 Q1 1 0.8864 0.1427 0.4419 11.00000 0.05 0.20 Q2 1 0.7660 -0.0671 0.2921 11.00000 0.05 0.17 Q3 1 0.7127 -0.0968 0.3222 11.00000 0.05 0.16 Q4 1 0.8238 -0.1488 0.2505 11.00000 0.05 0.16 Q5 1 0.7675 0.2120 0.4767 11.00000 0.05 0.15 Q6 1 1.0114 0.0797 0.3633 11.00000 0.05 0.15 Q7 1 0.7418 0.3614 0.5574 11.00000 0.05 0.15 Q8 1 0.9936 0.3391 0.5801 11.00000 0.05 0.15 Q9 1 0.5736 -0.0394 0.2751 11.00000 0.05 0.14 Q10 1 0.9241 0.3798 0.5449 11.00000 0.05 0.14 ; _cod_data_source_file gp5047.cif _cod_data_source_block Fpp-10-124 _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_sg_symbol_H-M 'P 21/c' _cod_database_code 2105074 _cod_database_fobs_code 2105074 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 F14 0.87229(18) 0.45954(8) 0.64358(6) 0.0755(3) Uani d . 1 1 O O1 1.09479(15) 0.04913(8) 0.40012(6) 0.0476(2) Uani d . 1 1 C C1 0.9023(2) 0.09065(10) 0.41083(7) 0.0341(2) Uani d . 1 1 N N1 0.69275(19) 0.05257(9) 0.36941(7) 0.0412(3) Uani d . 1 1 H H1 0.580(3) 0.1009(14) 0.3682(10) 0.056(4) Uiso d . 1 1 C C11 0.88200(19) 0.19020(9) 0.47152(7) 0.0329(2) Uani d . 1 1 C C12 1.0667(2) 0.26980(10) 0.48104(7) 0.0374(3) Uani d . 1 1 H H12 1.1945 0.2612 0.4486 0.045 Uiso calc R 1 1 C C13 1.0623(2) 0.36165(11) 0.53823(8) 0.0441(3) Uani d . 1 1 H H13 1.1841 0.4161 0.5442 0.053 Uiso calc R 1 1 C C14 0.8731(2) 0.37027(11) 0.58611(8) 0.0470(3) Uani d . 1 1 C C15 0.6888(2) 0.29287(12) 0.57928(8) 0.0476(3) Uani d . 1 1 H H15 0.5641 0.3011 0.6132 0.057 Uiso calc R 1 1 C C16 0.6921(2) 0.20211(11) 0.52079(8) 0.0400(3) Uani d . 1 1 H H16 0.5676 0.1491 0.5144 0.048 Uiso calc R 1 1 C C21 0.6588(2) -0.04089(10) 0.31169(7) 0.0341(3) Uani d . 1 1 C C22 0.4453(2) -0.04844(11) 0.25949(8) 0.0421(3) Uani d . 1 1 H H22 0.3285 0.0077 0.2630 0.051 Uiso calc R 1 1 C C23 0.4089(2) -0.13984(12) 0.20268(9) 0.0468(3) Uani d . 1 1 H H23 0.2654 -0.1429 0.1679 0.056 Uiso calc R 1 1 N N24 0.56608(19) -0.22482(9) 0.19388(7) 0.0445(3) Uani d . 1 1 C C25 0.7683(2) -0.21652(10) 0.24539(8) 0.0409(3) Uani d . 1 1 H H25 0.8806 -0.2747 0.2412 0.049 Uiso calc R 1 1 C C26 0.8241(2) -0.12859(10) 0.30433(7) 0.0378(3) Uani d . 1 1 H H26 0.9689 -0.1279 0.3384 0.045 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 0.0856(7) 0.0658(6) 0.0754(6) 0.0075(5) 0.0098(5) -0.0398(5) O1 0.0405(5) 0.0442(5) 0.0590(6) 0.0031(4) 0.0094(4) -0.0136(4) C1 0.0400(6) 0.0309(5) 0.0313(5) 0.0040(4) 0.0031(4) 0.0010(4) N1 0.0406(5) 0.0393(5) 0.0417(5) 0.0114(4) -0.0049(4) -0.0106(4) C11 0.0366(5) 0.0327(5) 0.0283(5) 0.0071(4) -0.0018(4) 0.0011(4) C12 0.0393(6) 0.0374(6) 0.0354(6) 0.0046(5) 0.0031(4) 0.0011(5) C13 0.0469(7) 0.0360(6) 0.0478(7) 0.0009(5) -0.0024(5) -0.0036(5) C14 0.0555(7) 0.0427(7) 0.0415(7) 0.0134(6) -0.0022(5) -0.0127(5) C15 0.0433(7) 0.0573(8) 0.0429(7) 0.0133(6) 0.0073(5) -0.0074(6) C16 0.0368(6) 0.0433(6) 0.0392(6) 0.0044(5) 0.0014(5) -0.0017(5) C21 0.0394(6) 0.0330(6) 0.0299(5) 0.0005(4) 0.0040(4) -0.0011(4) C22 0.0356(6) 0.0439(7) 0.0466(7) 0.0039(5) 0.0031(5) -0.0073(5) C23 0.0374(6) 0.0531(8) 0.0487(7) -0.0034(5) -0.0012(5) -0.0114(6) N24 0.0457(6) 0.0424(6) 0.0454(6) -0.0046(4) 0.0048(4) -0.0113(5) C25 0.0457(6) 0.0337(6) 0.0436(6) 0.0030(5) 0.0057(5) -0.0035(5) C26 0.0410(6) 0.0352(6) 0.0361(6) 0.0043(5) -0.0014(5) -0.0006(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 124.09(11) O1 C1 C11 120.94(10) N1 C1 C11 114.96(9) C1 N1 C21 127.10(10) C1 N1 H1 115.0(11) C21 N1 H1 115.7(11) C12 C11 C16 119.80(10) C12 C11 C1 117.65(10) C16 C11 C1 122.48(10) C13 C12 C11 120.49(11) C13 C12 H12 119.8 C11 C12 H12 119.8 C14 C13 C12 118.12(12) C14 C13 H13 120.9 C12 C13 H13 120.9 F14 C14 C15 119.05(12) F14 C14 C13 117.80(13) C15 C14 C13 123.14(11) C14 C15 C16 118.49(11) C14 C15 H15 120.8 C16 C15 H15 120.8 C15 C16 C11 119.94(11) C15 C16 H16 120.0 C11 C16 H16 120.0 C26 C21 C22 117.58(10) C26 C21 N1 124.03(10) C22 C21 N1 118.38(10) C23 C22 C21 119.10(11) C23 C22 H22 120.4 C21 C22 H22 120.4 N24 C23 C22 124.42(11) N24 C23 H23 117.8 C22 C23 H23 117.8 C25 N24 C23 115.38(10) N24 C25 C26 125.13(11) N24 C25 H25 117.4 C26 C25 H25 117.4 C25 C26 C21 118.37(11) C25 C26 H26 120.8 C21 C26 H26 120.8 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F14 C14 1.3591(14) O1 C1 1.2195(14) C1 N1 1.3641(15) C1 C11 1.4931(15) N1 C21 1.3983(14) N1 H1 0.848(16) C11 C12 1.3871(16) C11 C16 1.3921(16) C12 C13 1.3803(16) C12 H12 0.9300 C13 C14 1.3722(19) C13 H13 0.9300 C14 C15 1.368(2) C15 C16 1.3835(17) C15 H15 0.9300 C16 H16 0.9300 C21 C26 1.3888(16) C21 C22 1.3894(16) C22 C23 1.3724(17) C22 H22 0.9300 C23 N24 1.3386(16) C23 H23 0.9300 N24 C25 1.3327(16) C25 C26 1.3770(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 0.848(16) 2.335(17) 3.0581(15) 143.5(14) yes C26 H26 O1 . 0.93 2.33 2.8738(15) 117 yes C26 H26 Cg1 3_756 0.93 2.77 3.4183(12) 127 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 2.8(2) C11 C1 N1 C21 -177.77(10) O1 C1 C11 C12 31.87(16) N1 C1 C11 C12 -147.60(11) O1 C1 C11 C16 -145.11(12) N1 C1 C11 C16 35.41(15) C16 C11 C12 C13 -0.82(17) C1 C11 C12 C13 -177.89(10) C11 C12 C13 C14 1.20(18) C12 C13 C14 F14 178.68(11) C12 C13 C14 C15 -0.5(2) F14 C14 C15 C16 -179.75(11) C13 C14 C15 C16 -0.6(2) C14 C15 C16 C11 0.96(18) C12 C11 C16 C15 -0.28(17) C1 C11 C16 C15 176.64(11) C1 N1 C21 C26 17.61(19) C1 N1 C21 C22 -163.76(12) C26 C21 C22 C23 -1.08(18) N1 C21 C22 C23 -179.80(11) C21 C22 C23 N24 0.6(2) C22 C23 N24 C25 0.27(19) C23 N24 C25 C26 -0.59(18) N24 C25 C26 C21 0.06(19) C22 C21 C26 C25 0.79(17) N1 C21 C26 C25 179.43(11)