#------------------------------------------------------------------------------ #$Date: 2017-10-13 06:28:26 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201972 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/50/2105079.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_2105079 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 424 _chemical_name_common Fmm _chemical_name_systematic 3-Fluoro-N-(pyridin-3-yl)benzamide _space_group_IT_number 29 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2ac' _symmetry_space_group_name_H-M 'P c a 21' _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 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.3020(3) _cell_length_b 11.8371(3) _cell_length_c 7.6218(2) _cell_measurement_reflns_used 3744 _cell_measurement_temperature 294.0(10) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 2.55 _cell_volume 1019.67(5) _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 0.953 _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 0.0205 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 7366 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 27.79 _diffrn_reflns_theta_min 2.49 _diffrn_standards_decay_% 1 _diffrn_standards_interval_time 60 _diffrn_standards_number 7839 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_T_max 0.9917 _exptl_absorpt_correction_T_min 0.9613 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(ABSFAC, Clark and Reid, 1998)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 448 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.152 _refine_diff_density_min -0.148 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 149 _refine_ls_number_reflns 1239 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.023 _refine_ls_R_factor_all 0.0470 _refine_ls_R_factor_gt 0.0330 _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^)+(0.0521P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0799 _refine_ls_wR_factor_ref 0.0836 _reflns_number_gt 981 _reflns_number_total 1239 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL 10-122 is Fmm in Pca21 at RT with Mo at 40kV30mA to 0.80\%A CELL 0.71073 11.3020 11.8371 7.6218 90.000 90.000 90.000 ZERR 4 0.0003 0.0003 0.0002 0.000 0.000 0.000 LATT -1 SYMM -X,-Y,1/2+Z SYMM 1/2+X,-Y,Z SYMM 1/2 -X,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 0.5+X,1-Y,Z EQIV $3 0.5+X,-Y,Z EQIV $4 -X,1-Y,Z-0.5 EQIV $5 0.5-X,1+Y,Z-0.5 HTAB N1 N23_$2 HTAB C22 O1 HTAB C14 O1_$3 HTAB C24 O1_$4 HTAB C25 F13_$5 RTAB FC F13 C13 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 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 0.08 0.10 0.38 TEMP 21 PLAN 10 MPLA 6 C11 C12 C13 C14 C15 C16 F13 N23 MPLA 3 O1 N1 C1 C11 C21 F13 N23 MPLA 6 C21 C22 N23 C24 C25 C26 F13 N23 MPLA 6 C11 C12 C13 C14 C15 C16 MPLA 5 O1 N1 C1 C11 C21 F13 MPLA 6 C21 C22 N23 C24 C25 C26 WGHT 0.052100 FVAR 7.59552 MOLE 1 F13 5 0.304251 -0.122231 0.322345 11.00000 0.10670 0.04019 = 0.13555 -0.00287 0.01586 -0.00157 O1 4 0.117244 0.261178 0.350311 11.00000 0.03747 0.04689 = 0.10306 0.00563 0.01276 -0.00185 C1 1 0.222880 0.275338 0.329323 11.00000 0.03885 0.03972 = 0.04921 -0.00488 0.00302 0.00009 N1 3 0.271098 0.372716 0.271534 11.00000 0.03004 0.03973 = 0.06115 0.00156 0.00423 0.00254 H1 2 0.337983 0.379886 0.253831 11.00000 0.06559 C11 1 0.308147 0.180373 0.362374 11.00000 0.04135 0.04056 = 0.04618 0.00154 0.00404 0.00039 C12 1 0.268838 0.071970 0.325793 11.00000 0.04900 0.04264 = 0.05737 -0.00099 0.00314 -0.00153 AFIX 43 H12 2 0.193969 0.059897 0.278766 11.00000 -1.20000 AFIX 0 C13 1 0.342755 -0.016940 0.360476 11.00000 0.06381 0.03729 = 0.07380 0.00408 0.01620 0.00017 C14 1 0.452528 -0.004130 0.430399 11.00000 0.05946 0.05290 = 0.08826 0.02335 0.01375 0.01384 AFIX 43 H14 2 0.500301 -0.066397 0.453165 11.00000 -1.20000 AFIX 0 C15 1 0.490649 0.102973 0.466279 11.00000 0.04908 0.06984 = 0.08260 0.02291 -0.00633 0.00396 AFIX 43 H15 2 0.565638 0.113852 0.513588 11.00000 -1.20000 AFIX 0 C16 1 0.419071 0.195560 0.433113 11.00000 0.04782 0.04509 = 0.06352 0.00628 -0.00297 -0.00275 AFIX 43 H16 2 0.445967 0.267968 0.458643 11.00000 -1.20000 AFIX 0 C21 1 0.210513 0.472225 0.223643 11.00000 0.03509 0.03614 = 0.04557 -0.00486 0.00006 -0.00021 C22 1 0.090612 0.490072 0.251291 11.00000 0.03617 0.04171 = 0.06769 0.00121 0.00200 0.00109 AFIX 43 H22 2 0.046446 0.433334 0.304532 11.00000 -1.20000 AFIX 0 N23 3 0.035978 0.585869 0.204269 11.00000 0.03996 0.04498 = 0.08535 0.00313 -0.00058 0.00563 C24 1 0.099224 0.666110 0.127068 11.00000 0.05168 0.03853 = 0.07455 0.00281 -0.00471 0.00401 AFIX 43 H24 2 0.061348 0.732339 0.093091 11.00000 -1.20000 AFIX 0 C25 1 0.218053 0.655499 0.095277 11.00000 0.04956 0.04141 = 0.06161 0.00481 0.00526 -0.00483 AFIX 43 H25 2 0.259941 0.713575 0.041469 11.00000 -1.20000 AFIX 0 C26 1 0.274080 0.557676 0.144256 11.00000 0.03584 0.04667 = 0.05552 -0.00231 0.00353 0.00053 AFIX 43 H26 2 0.354710 0.548938 0.124027 11.00000 -1.20000 HKLF 4 REM 10-122 is Fmm in Pca21 at RT with Mo at 40kV30mA to 0.80\%A REM R1 = 0.0330 for 981 Fo > 4sig(Fo) and 0.0470 for all 1239 data REM 149 parameters refined using 1 restraints END WGHT 0.0521 0.0000 REM Highest difference peak 0.152, deepest hole -0.148, 1-sigma level 0.030 Q1 1 0.5836 0.1333 0.5707 11.00000 0.05 0.15 Q2 1 -0.0507 0.5867 0.2590 11.00000 0.05 0.11 Q3 1 -0.0355 0.5817 0.1360 11.00000 0.05 0.11 Q4 1 0.0561 0.5350 0.2247 11.00000 0.05 0.10 Q5 1 0.2723 0.2238 0.3231 11.00000 0.05 0.10 Q6 1 0.0459 0.4362 0.2356 11.00000 0.05 0.09 Q7 1 0.4065 0.3655 0.2604 11.00000 0.05 0.09 Q8 1 0.4845 -0.0877 0.3638 11.00000 0.05 0.08 Q9 1 0.1151 0.5401 -0.0299 11.00000 0.05 0.08 Q10 1 0.4213 -0.0167 0.3063 11.00000 0.05 0.08 ; _cod_data_source_file gp5047.cif _cod_data_source_block Fmm-10-122 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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 2105079 _cod_database_fobs_code 2105079 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, 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 0.30425(15) -0.12223(10) 0.3223(3) 0.0941(6) Uani d . 1 1 O O1 0.11724(13) 0.26118(12) 0.3503(3) 0.0625(5) Uani d . 1 1 C C1 0.22288(17) 0.27534(15) 0.3293(3) 0.0426(5) Uani d . 1 1 N N1 0.27110(16) 0.37272(14) 0.2715(3) 0.0436(4) Uani d . 1 1 H H1 0.338(3) 0.380(2) 0.254(4) 0.066(8) Uiso d . 1 1 C C11 0.30815(16) 0.18037(16) 0.3624(3) 0.0427(5) Uani d . 1 1 C C12 0.2688(2) 0.07197(14) 0.3258(3) 0.0497(5) Uani d . 1 1 H H12 0.1940 0.0599 0.2788 0.060 Uiso calc R 1 1 C C13 0.3428(2) -0.01694(18) 0.3605(4) 0.0583(6) Uani d . 1 1 C C14 0.4525(2) -0.0041(2) 0.4304(4) 0.0669(7) Uani d . 1 1 H H14 0.5003 -0.0664 0.4532 0.080 Uiso calc R 1 1 C C15 0.4906(2) 0.1030(2) 0.4663(4) 0.0672(7) Uani d . 1 1 H H15 0.5656 0.1139 0.5136 0.081 Uiso calc R 1 1 C C16 0.4191(2) 0.19556(18) 0.4331(3) 0.0521(6) Uani d . 1 1 H H16 0.4460 0.2680 0.4586 0.063 Uiso calc R 1 1 C C21 0.21051(16) 0.47223(16) 0.2236(3) 0.0389(4) Uani d . 1 1 C C22 0.09061(18) 0.49007(18) 0.2513(3) 0.0485(6) Uani d . 1 1 H H22 0.0464 0.4333 0.3045 0.058 Uiso calc R 1 1 N N23 0.03598(16) 0.58587(15) 0.2043(3) 0.0568(5) Uani d . 1 1 C C24 0.09922(19) 0.66611(18) 0.1271(4) 0.0549(6) Uani d . 1 1 H H24 0.0613 0.7323 0.0931 0.066 Uiso calc R 1 1 C C25 0.21805(18) 0.65550(18) 0.0953(3) 0.0509(6) Uani d . 1 1 H H25 0.2599 0.7136 0.0415 0.061 Uiso calc R 1 1 C C26 0.27408(18) 0.55768(15) 0.1443(3) 0.0460(5) Uani d . 1 1 H H26 0.3547 0.5489 0.1240 0.055 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 0.1067(13) 0.0402(7) 0.1355(17) -0.0016(7) 0.0159(13) -0.0029(10) O1 0.0375(8) 0.0469(8) 0.1031(15) -0.0019(6) 0.0128(8) 0.0056(10) C1 0.0389(11) 0.0397(10) 0.0492(12) 0.0001(8) 0.0030(10) -0.0049(10) N1 0.0300(9) 0.0397(8) 0.0612(11) 0.0025(7) 0.0042(9) 0.0016(7) C11 0.0413(10) 0.0406(10) 0.0462(12) 0.0004(8) 0.0040(9) 0.0015(9) C12 0.0490(12) 0.0426(11) 0.0574(13) -0.0015(9) 0.0031(11) -0.0010(11) C13 0.0638(15) 0.0373(11) 0.0738(18) 0.0002(10) 0.0162(13) 0.0041(12) C14 0.0595(15) 0.0529(13) 0.0883(19) 0.0138(12) 0.0138(14) 0.0233(13) C15 0.0491(13) 0.0698(17) 0.0826(18) 0.0040(12) -0.0063(13) 0.0229(13) C16 0.0478(12) 0.0451(12) 0.0635(14) -0.0027(10) -0.0030(11) 0.0063(11) C21 0.0351(10) 0.0361(10) 0.0456(11) -0.0002(8) 0.0001(9) -0.0049(8) C22 0.0362(10) 0.0417(11) 0.0677(15) 0.0011(8) 0.0020(10) 0.0012(10) N23 0.0400(10) 0.0450(9) 0.0853(15) 0.0056(8) -0.0006(10) 0.0031(10) C24 0.0517(14) 0.0385(11) 0.0745(17) 0.0040(9) -0.0047(12) 0.0028(11) C25 0.0496(14) 0.0414(10) 0.0616(14) -0.0048(9) 0.0053(11) 0.0048(10) C26 0.0358(11) 0.0467(11) 0.0555(12) 0.0005(8) 0.0035(10) -0.0023(10) 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 123.87(18) O1 C1 C11 120.31(17) N1 C1 C11 115.79(17) C1 N1 C21 127.01(17) C1 N1 H1 123.1(19) C21 N1 H1 109.8(19) C16 C11 C12 119.44(19) C16 C11 C1 123.53(18) C12 C11 C1 116.96(17) C13 C12 C11 118.5(2) C13 C12 H12 120.8 C11 C12 H12 120.8 F13 C13 C14 118.8(2) F13 C13 C12 118.1(2) C14 C13 C12 123.2(2) C13 C14 C15 118.0(2) C13 C14 H14 121.0 C15 C14 H14 121.0 C14 C15 C16 120.9(2) C14 C15 H15 119.6 C16 C15 H15 119.6 C11 C16 C15 120.0(2) C11 C16 H16 120.0 C15 C16 H16 120.0 C26 C21 C22 117.60(18) C26 C21 N1 118.21(16) C22 C21 N1 124.19(18) N23 C22 C21 122.56(19) N23 C22 H22 118.7 C21 C22 H22 118.7 C24 N23 C22 118.44(18) N23 C24 C25 122.7(2) N23 C24 H24 118.6 C25 C24 H24 118.6 C24 C25 C26 118.80(19) C24 C25 H25 120.6 C26 C25 H25 120.6 C25 C26 C21 119.85(19) C25 C26 H26 120.1 C21 C26 H26 120.1 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F13 C13 1.352(3) O1 C1 1.216(2) C1 N1 1.349(2) C1 C11 1.502(3) N1 C21 1.411(2) N1 H1 0.77(3) C11 C16 1.376(3) C11 C12 1.386(3) C12 C13 1.369(3) C12 H12 0.9300 C13 C14 1.359(4) C14 C15 1.367(4) C14 H14 0.9300 C15 C16 1.385(3) C15 H15 0.9300 C16 H16 0.9300 C21 C26 1.380(3) C21 C22 1.388(2) C22 N23 1.340(3) C22 H22 0.9300 N23 C24 1.326(3) C24 C25 1.370(3) C24 H24 0.9300 C25 C26 1.372(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 3_565 0.77(3) 2.31(3) 3.077(3) 176(3) yes C22 H22 O1 . 0.93 2.22 2.829(3) 123 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 -1.0(4) C11 C1 N1 C21 177.0(2) O1 C1 C11 C16 -143.9(2) N1 C1 C11 C16 37.9(3) O1 C1 C11 C12 33.1(3) N1 C1 C11 C12 -145.0(2) C16 C11 C12 C13 -0.5(3) C1 C11 C12 C13 -177.6(2) C11 C12 C13 F13 -179.2(2) C11 C12 C13 C14 0.5(4) F13 C13 C14 C15 179.2(3) C12 C13 C14 C15 -0.5(4) C13 C14 C15 C16 0.3(4) C12 C11 C16 C15 0.3(4) C1 C11 C16 C15 177.3(2) C14 C15 C16 C11 -0.3(4) C1 N1 C21 C26 -171.0(2) C1 N1 C21 C22 9.1(3) C26 C21 C22 N23 -0.1(3) N1 C21 C22 N23 179.9(2) C21 C22 N23 C24 0.6(4) C22 N23 C24 C25 -0.7(4) N23 C24 C25 C26 0.4(4) C24 C25 C26 C21 0.1(4) C22 C21 C26 C25 -0.3(3) N1 C21 C26 C25 179.8(2) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 676282