# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Thomas, Lynne' 'Craig, Gavin' 'Gutmann, Matthias' 'Parkin, Andrew' 'Shankland, Kenneth' 'Wilson, Chick' _publ_contact_author_name 'Thomas, Lynne' _publ_contact_author_email L.H.Thomas@bath.ac.uk _publ_section_title ; Conformational Polymorphism of the Molecular Complex of 3-Fluorobenzoic acid with 4-Acetylpyridine ; data_I _database_code_depnum_ccdc_archive 'CCDC 722105' _audit_creation_method 'WinGX routine CIF_UPDATE' _chemical_name_systematic ; 3-Fluorobenzoic acid--4-acetylpyridine (1/1) ; _chemical_formula_moiety 'C7 H5 F O2 , C7 H7 N O' _chemical_formula_sum 'C14 H12 F N O3' _chemical_formula_iupac 'C7 H5 F O2 , C7 H7 N O' _chemical_formula_weight 261.25 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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' _cell_length_a 10.0498(11) _cell_length_b 10.5779(8) _cell_length_c 11.5045(8) _cell_angle_alpha 90 _cell_angle_beta 92.026(4) _cell_angle_gamma 90 _cell_volume 1222.23(18) _cell_formula_units_Z 4 _cell_measurement_reflns_used 10265 _cell_measurement_theta_min 3 _cell_measurement_theta_max 28 _cell_measurement_temperature 100(2) _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.42 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.11 _exptl_absorpt_correction_type none _diffrn_ambient_temperature 100(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID IP image-plate' _diffrn_measurement_method \w _diffrn_reflns_number 15130 _diffrn_reflns_av_R_equivalents 0.031 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _reflns_number_total 2787 _reflns_number_gt 1888 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_gt 0.035 _refine_ls_wR_factor_ref 0.0986 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_number_reflns 2787 _refine_ls_number_parameters 220 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0573P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.001 _refine_diff_density_max 0.23 _refine_diff_density_min -0.208 _refine_ls_extinction_method none 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 0 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'CrystalClear (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear (Rigaku, 2008)' _computing_data_reduction 'CrystalClear (Rigaku, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)' _computing_publication_material 'WinGX (Farrugia, 1999)' 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 _atom_site_disorder_assembly _atom_site_disorder_group F F1 0.86852(8) 0.91451(8) 0.42397(7) 0.0336(2) Uani d PD 0.96 1 A 1 C C2 0.80192(13) 0.81276(12) 0.46507(11) 0.0243(3) Uani d PD 0.96 1 A 1 C C2A 0.80192(13) 0.81276(12) 0.46507(11) 0.0243(3) Uani d P 0.04 1 A 2 H H2A 0.8481 0.8820 0.4373 0.029 Uiso calc PR 0.04 1 A 2 C C3 0.67564(13) 0.83201(12) 0.50485(11) 0.0220(3) Uani d . 1 1 . . H H3 0.6362(14) 0.9146(14) 0.5003(11) 0.024(4) Uiso d . 1 1 . . C C4 0.60718(12) 0.72721(12) 0.54569(10) 0.0203(3) Uani d . 1 1 A . C C5 0.66565(13) 0.60822(12) 0.54596(10) 0.0229(3) Uani d . 1 1 . . H H5 0.6176(15) 0.5344(14) 0.5736(12) 0.029(4) Uiso d . 1 1 . . C C6 0.79390(13) 0.59376(13) 0.50555(11) 0.0251(3) Uani d P 0.96 1 A 1 H H6 0.8334 0.5142 0.5063 0.030 Uiso calc PR 0.96 1 A 1 C C6A 0.79390(13) 0.59376(13) 0.50555(11) 0.0251(3) Uani d PD 0.04 1 A 2 F F1A 0.8666(19) 0.4867(15) 0.5104(17) 0.033(4) Uiso d PD 0.04 1 A 2 C C7 0.86291(14) 0.69651(13) 0.46440(11) 0.0256(3) Uani d . 1 1 . . H H7 0.9528(16) 0.6854(14) 0.4351(12) 0.027(4) Uiso d . 1 1 . . C C8 0.46965(13) 0.74749(11) 0.58875(10) 0.0211(3) Uani d . 1 1 . . O O9 0.41636(10) 0.64448(9) 0.63191(8) 0.0299(2) Uani d . 1 1 A . H H9 0.325(2) 0.6594(19) 0.6527(17) 0.068(6) Uiso d . 1 1 . . O O10 0.41357(9) 0.84903(9) 0.58340(8) 0.0287(2) Uani d . 1 1 A . N N11 0.16961(11) 0.68081(10) 0.69676(9) 0.0235(3) Uani d . 1 1 . . C C12 0.09586(13) 0.58338(13) 0.73125(11) 0.0235(3) Uani d . 1 1 . . H H12 0.1365(15) 0.4988(14) 0.7270(11) 0.026(4) Uiso d . 1 1 . . C C13 0.11730(14) 0.79700(13) 0.70272(11) 0.0254(3) Uani d . 1 1 . . H H13 0.1748(15) 0.8649(15) 0.6758(12) 0.030(4) Uiso d . 1 1 . . C C14 -0.00901(13) 0.81965(13) 0.74237(11) 0.0240(3) Uani d . 1 1 . . H H14 -0.0396(15) 0.9059(16) 0.7441(13) 0.033(4) Uiso d . 1 1 . . C C15 -0.03229(13) 0.59762(12) 0.77072(10) 0.0213(3) Uani d . 1 1 . . H H15 -0.0813(14) 0.5233(14) 0.7917(12) 0.026(4) Uiso d . 1 1 . . C C16 -0.08659(12) 0.71782(12) 0.77594(10) 0.0208(3) Uani d . 1 1 . . C C17 -0.22611(13) 0.74106(12) 0.81607(10) 0.0222(3) Uani d . 1 1 . . O O18 -0.26975(10) 0.84818(9) 0.81733(9) 0.0327(3) Uani d . 1 1 . . C C19 -0.30654(14) 0.63097(14) 0.85455(13) 0.0282(3) Uani d . 1 1 . . H H19A -0.399(2) 0.6527(17) 0.8522(15) 0.049(5) Uiso d . 1 1 . . H H19B -0.2946(17) 0.5564(17) 0.8057(14) 0.045(5) Uiso d . 1 1 . . H H19C -0.2765(17) 0.6106(17) 0.9328(15) 0.050(5) Uiso d . 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 F1 0.0277(5) 0.0260(5) 0.0480(5) -0.0030(3) 0.0144(4) 0.0045(4) C2 0.0239(7) 0.0238(7) 0.0255(7) -0.0041(5) 0.0044(5) 0.0021(5) C2A 0.0239(7) 0.0238(7) 0.0255(7) -0.0041(5) 0.0044(5) 0.0021(5) C3 0.0236(7) 0.0210(7) 0.0215(6) 0.0006(5) 0.0014(5) -0.0009(5) C4 0.0203(6) 0.0220(7) 0.0186(6) -0.0006(5) 0.0003(5) -0.0013(5) C5 0.0258(7) 0.0223(7) 0.0207(6) -0.0009(5) 0.0013(5) 0.0016(5) C6 0.0265(7) 0.0232(7) 0.0257(6) 0.0045(5) 0.0031(5) -0.0007(5) C6A 0.0265(7) 0.0232(7) 0.0257(6) 0.0045(5) 0.0031(5) -0.0007(5) C7 0.0215(7) 0.0299(7) 0.0255(7) 0.0032(5) 0.0047(5) 0.0010(5) C8 0.0203(6) 0.0209(7) 0.0221(6) -0.0018(5) 0.0008(5) -0.0012(5) O9 0.0223(5) 0.0251(5) 0.0428(6) -0.0002(4) 0.0101(4) 0.0039(4) O10 0.0251(5) 0.0224(5) 0.0391(5) 0.0015(4) 0.0081(4) 0.0013(4) N11 0.0207(5) 0.0241(6) 0.0259(6) -0.0014(4) 0.0029(4) 0.0015(4) C12 0.0235(7) 0.0224(7) 0.0247(7) 0.0011(5) 0.0029(5) -0.0003(5) C13 0.0254(7) 0.0230(7) 0.0278(7) -0.0033(6) 0.0015(5) 0.0021(5) C14 0.0256(7) 0.0189(7) 0.0275(7) 0.0002(5) -0.0006(5) -0.0003(5) C15 0.0220(6) 0.0189(7) 0.0231(6) -0.0010(5) 0.0018(5) 0.0009(5) C16 0.0197(6) 0.0227(7) 0.0199(6) 0.0000(5) -0.0018(5) -0.0021(5) C17 0.0211(7) 0.0225(7) 0.0228(6) 0.0018(5) -0.0013(5) -0.0037(5) O18 0.0270(5) 0.0236(5) 0.0477(6) 0.0054(4) 0.0055(4) -0.0027(4) C19 0.0205(7) 0.0279(8) 0.0364(8) 0.0003(6) 0.0048(6) -0.0001(6) _geom_special_details ; All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag F1 C2 . 1.3611(15) ? C2 C7 . 1.3740(19) ? C2 C3 . 1.3794(18) ? C3 C4 . 1.3949(18) ? C3 H3 . 0.960(15) ? C4 C5 . 1.3890(18) ? C4 C8 . 1.5001(18) ? C5 C6 . 1.3940(18) ? C5 H5 . 0.978(15) ? C6 C7 . 1.3819(19) ? C6 H6 . 0.9300 ? C7 H7 . 0.982(16) ? C8 O10 . 1.2135(15) ? C8 O9 . 1.3189(15) ? O9 H9 . 0.97(2) ? N11 C12 . 1.3378(17) ? N11 C13 . 1.3394(17) ? C12 C15 . 1.3888(18) ? C12 H12 . 0.985(15) ? C13 C14 . 1.3848(19) ? C13 H13 . 0.979(16) ? C14 C16 . 1.3923(18) ? C14 H14 . 0.963(16) ? C15 C16 . 1.3858(18) ? C15 H15 . 0.963(15) ? C16 C17 . 1.5118(17) ? C17 O18 . 1.2153(15) ? C17 C19 . 1.4935(19) ? C19 H19A . 0.955(19) ? C19 H19B . 0.978(17) ? C19 H19C . 0.964(18) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag F1 C2 C7 . . 118.74(11) ? F1 C2 C3 . . 117.91(12) ? C7 C2 C3 . . 123.35(12) ? C2 C3 C4 . . 117.71(12) ? C2 C3 H3 . . 119.9(8) ? C4 C3 H3 . . 122.3(8) ? C5 C4 C3 . . 120.48(12) ? C5 C4 C8 . . 121.57(11) ? C3 C4 C8 . . 117.95(11) ? C4 C5 C6 . . 119.65(12) ? C4 C5 H5 . . 120.7(9) ? C6 C5 H5 . . 119.6(9) ? C7 C6 C5 . . 120.60(13) ? C7 C6 H6 . . 119.7 ? C5 C6 H6 . . 119.7 ? C2 C7 C6 . . 118.20(12) ? C2 C7 H7 . . 121.6(9) ? C6 C7 H7 . . 120.2(9) ? O10 C8 O9 . . 123.80(12) ? O10 C8 C4 . . 122.79(11) ? O9 C8 C4 . . 113.41(11) ? C8 O9 H9 . . 111.0(12) ? C12 N11 C13 . . 117.97(11) ? N11 C12 C15 . . 122.91(12) ? N11 C12 H12 . . 116.7(9) ? C15 C12 H12 . . 120.4(9) ? N11 C13 C14 . . 122.79(12) ? N11 C13 H13 . . 114.8(9) ? C14 C13 H13 . . 122.4(9) ? C13 C14 C16 . . 119.10(12) ? C13 C14 H14 . . 117.9(9) ? C16 C14 H14 . . 123.0(9) ? C16 C15 C12 . . 119.00(12) ? C16 C15 H15 . . 122.1(9) ? C12 C15 H15 . . 118.8(9) ? C15 C16 C14 . . 118.20(12) ? C15 C16 C17 . . 122.23(11) ? C14 C16 C17 . . 119.57(12) ? O18 C17 C19 . . 121.61(12) ? O18 C17 C16 . . 119.62(12) ? C19 C17 C16 . . 118.77(11) ? C17 C19 H19A . . 109.9(11) ? C17 C19 H19B . . 112.3(10) ? H19A C19 H19B . . 108.4(14) ? C17 C19 H19C . . 107.2(11) ? H19A C19 H19C . . 110.6(14) ? H19B C19 H19C . . 108.4(14) ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag F1 C2 C3 C4 . . . . 179.30(11) ? C7 C2 C3 C4 . . . . -0.3(2) ? C2 C3 C4 C5 . . . . 0.14(18) ? C2 C3 C4 C8 . . . . -179.83(11) ? C3 C4 C5 C6 . . . . 0.28(18) ? C8 C4 C5 C6 . . . . -179.75(11) ? C4 C5 C6 C7 . . . . -0.5(2) ? F1 C2 C7 C6 . . . . -179.53(11) ? C3 C2 C7 C6 . . . . 0.1(2) ? C5 C6 C7 C2 . . . . 0.3(2) ? C5 C4 C8 O10 . . . . -175.77(11) ? C3 C4 C8 O10 . . . . 4.20(19) ? C5 C4 C8 O9 . . . . 3.87(17) ? C3 C4 C8 O9 . . . . -176.16(11) ? C13 N11 C12 C15 . . . . 1.11(19) ? C12 N11 C13 C14 . . . . -0.25(19) ? N11 C13 C14 C16 . . . . -1.1(2) ? N11 C12 C15 C16 . . . . -0.61(19) ? C12 C15 C16 C14 . . . . -0.72(18) ? C12 C15 C16 C17 . . . . 179.02(11) ? C13 C14 C16 C15 . . . . 1.51(19) ? C13 C14 C16 C17 . . . . -178.24(11) ? C15 C16 C17 O18 . . . . -178.87(11) ? C14 C16 C17 O18 . . . . 0.87(18) ? C15 C16 C17 C19 . . . . 1.77(18) ? C14 C16 C17 C19 . . . . -178.49(12) ? 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 O9 H9 N11 . 0.97(2) 1.68(2) 2.6428(14) 176.3(18) C19 H19C O10 4_576 0.96(2) 2.57(2) 3.385(2) 142.5(14) C13 H13 F1 3_676 0.98(2) 2.63(2) 3.3870(16) 134.3(12) #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_gac071200k _database_code_depnum_ccdc_archive 'CCDC 810545' #TrackingRef '- Xray_formI.cif' _audit_creation_date 2010-02-09T15:58:46-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C7 H7 N O, C7 H5 F O2' _chemical_formula_sum 'C14 H12 F N O3' _chemical_formula_weight 261.25 #============================================================================== # CRYSTAL DATA 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' _cell_length_a 10.0714(15) _cell_length_b 10.6513(12) _cell_length_c 11.6320(13) _cell_angle_alpha 90 _cell_angle_beta 91.677(5) _cell_angle_gamma 90 _cell_volume 1247.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 8734 _cell_measurement_theta_max 55.08 _cell_measurement_theta_min 6.52 _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8221 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'CrystalClear 1.4.0 (Rigaku, 2008)' #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID IP Image Plate diffractometer' _diffrn_reflns_number 15541 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_unetI/netI 0.0342 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 #============================================================================== # STRUCTURE SOLUTION _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 2851 _reflns_number_gt 1509 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0863 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.117 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_number_reflns 2851 _refine_ls_number_parameters 220 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0591P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.162 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.05 _refine_ls_extinction_method none 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 0 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol H11 0.6362(16) 0.9113(16) 0.4999(13) 0.045(4) Uiso d . 1 . . H H8 0.6171(17) 0.5392(16) 0.5731(13) 0.050(5) Uiso d . 1 . . H H4 0.1353(16) 0.5031(16) 0.7253(12) 0.044(4) Uiso d . 1 . . H H7 -0.275(2) 0.613(2) 0.929(2) 0.098(8) Uiso d . 1 . . H H3 -0.0819(16) 0.5282(17) 0.7917(13) 0.050(5) Uiso d . 1 . . H H2 -0.0419(17) 0.9041(18) 0.7444(14) 0.058(5) Uiso d . 1 . . H H10 0.9498(19) 0.6851(16) 0.4345(14) 0.051(5) Uiso d . 1 . . H H1 0.1733(18) 0.8654(17) 0.6782(14) 0.054(5) Uiso d . 1 . . H H5 -0.295(2) 0.560(2) 0.8070(19) 0.093(7) Uiso d . 1 . . H H6 -0.399(3) 0.656(2) 0.858(2) 0.107(9) Uiso d . 1 . . H H12 0.319(3) 0.663(2) 0.653(2) 0.103(8) Uiso d . 1 . . H O2 0.41492(12) 0.85030(11) 0.58433(12) 0.0570(4) Uani d . 1 . . O O1 -0.26956(13) 0.84885(12) 0.81715(12) 0.0656(4) Uani d . 1 . . O F1 0.86809(10) 0.91210(10) 0.42405(10) 0.0662(4) Uani d PD 0.94 A 1 F C11 0.80088(17) 0.81137(16) 0.46480(14) 0.0458(4) Uani d PD 0.94 A 1 C C9 0.79122(17) 0.59507(17) 0.50483(14) 0.0474(4) Uani d PD 0.94 A 1 C H9 0.8301 0.5158 0.5055 0.057 Uiso calc PR 0.94 A 1 H F1A 0.866(2) 0.4888(18) 0.512(2) 0.093(7) Uiso d PD 0.06 A 2 F C11A 0.80088(17) 0.81137(16) 0.46480(14) 0.0458(4) Uani d P 0.06 A 2 C H11A 0.8475 0.8798 0.437 0.055 Uiso calc PR 0.06 A 2 H C9A 0.79122(17) 0.59507(17) 0.50483(14) 0.0474(4) Uani d P 0.06 A 2 C N1 0.16838(14) 0.68354(13) 0.69607(12) 0.0458(4) Uani d . 1 . . N O3 0.41482(13) 0.64727(11) 0.62983(12) 0.0585(4) Uani d . 1 A . O C10 0.86043(18) 0.69593(16) 0.46400(15) 0.0484(4) Uani d . 1 . . C C6 -0.22572(17) 0.74289(16) 0.81641(14) 0.0439(4) Uani d . 1 . . C C4 -0.03261(16) 0.60111(15) 0.76997(13) 0.0405(4) Uani d . 1 . . C C5 0.09442(16) 0.58706(17) 0.73019(14) 0.0446(4) Uani d . 1 . . C C13 0.60599(15) 0.72845(14) 0.54522(13) 0.0375(4) Uani d . 1 A . C C7 -0.3058(2) 0.6346(2) 0.8555(2) 0.0556(5) Uani d . 1 . . C C3 -0.08729(16) 0.71987(15) 0.77531(12) 0.0378(4) Uani d . 1 . . C C12 0.67556(17) 0.83115(16) 0.50467(14) 0.0422(4) Uani d . 1 . . C C8 0.66360(17) 0.61022(16) 0.54524(14) 0.0440(4) Uani d . 1 . . C C2 -0.00963(18) 0.82027(17) 0.74179(15) 0.0458(4) Uani d . 1 . . C C14 0.46951(16) 0.74918(15) 0.58813(13) 0.0407(4) Uani d . 1 . . C C1 0.11563(18) 0.79850(17) 0.70223(15) 0.0489(4) Uani d . 1 . . C 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 O2 0.0465(7) 0.0434(7) 0.0821(9) 0.0034(6) 0.0178(6) 0.0021(6) O1 0.0533(8) 0.0466(8) 0.0974(10) 0.0112(6) 0.0120(7) -0.0068(7) F1 0.0520(7) 0.0510(7) 0.0971(9) -0.0067(5) 0.0273(6) 0.0083(6) C11 0.0418(10) 0.0434(10) 0.0525(10) -0.0068(7) 0.0092(8) 0.0039(7) C9 0.0466(10) 0.0429(10) 0.0528(10) 0.0070(8) 0.0059(8) 0.0015(8) C11A 0.0418(10) 0.0434(10) 0.0525(10) -0.0068(7) 0.0092(8) 0.0039(7) C9A 0.0466(10) 0.0429(10) 0.0528(10) 0.0070(8) 0.0059(8) 0.0015(8) N1 0.0392(8) 0.0464(9) 0.0522(8) -0.0031(6) 0.0074(6) 0.0029(6) O3 0.0435(7) 0.0477(7) 0.0854(9) -0.0029(6) 0.0204(7) 0.0077(6) C10 0.0388(10) 0.0538(11) 0.0531(10) 0.0041(8) 0.0100(8) 0.0016(8) C6 0.0391(10) 0.0434(10) 0.0491(10) 0.0046(8) -0.0008(7) -0.0063(7) C4 0.0388(9) 0.0352(9) 0.0478(9) -0.0017(7) 0.0060(7) 0.0010(7) C5 0.0414(10) 0.0392(10) 0.0536(10) 0.0031(7) 0.0086(8) -0.0018(8) C13 0.0370(9) 0.0380(9) 0.0375(8) -0.0015(7) 0.0013(7) -0.0017(6) C7 0.0399(11) 0.0555(13) 0.0720(14) -0.0003(9) 0.0103(10) 0.0005(10) C3 0.0361(9) 0.0375(9) 0.0396(8) 0.0010(7) -0.0006(7) -0.0010(7) C12 0.0414(10) 0.0395(10) 0.0459(9) -0.0004(7) 0.0034(7) -0.0012(7) C8 0.0461(10) 0.0397(10) 0.0463(9) -0.0014(8) 0.0047(8) 0.0014(8) C2 0.0468(10) 0.0343(10) 0.0562(10) 0.0005(7) 0.0014(8) 0.0002(7) C14 0.0388(9) 0.0385(10) 0.0449(9) -0.0030(7) 0.0033(7) -0.0025(7) C1 0.0469(11) 0.0418(10) 0.0584(11) -0.0059(8) 0.0061(9) 0.0036(8) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O2 C14 . 1.2095(19) ? O1 C6 . 1.2121(19) ? F1 C11 . 1.3612(18) ? C11 C10 . 1.368(2) ? C11 C12 . 1.374(2) ? C9 C10 . 1.373(2) ? C9 C8 . 1.391(2) ? C9 H9 . 0.93 ? N1 C5 . 1.336(2) ? N1 C1 . 1.338(2) ? O3 C14 . 1.3162(19) ? O3 H12 . 1.02(3) ? C10 H10 . 0.979(19) ? C6 C7 . 1.487(3) ? C6 C3 . 1.507(2) ? C4 C5 . 1.381(2) ? C4 C3 . 1.382(2) ? C4 H3 . 0.960(17) ? C5 H4 . 0.987(16) ? C13 C8 . 1.387(2) ? C13 C12 . 1.389(2) ? C13 C14 . 1.492(2) ? C7 H7 . 0.93(2) ? C7 H5 . 0.98(2) ? C7 H6 . 0.97(3) ? C3 C2 . 1.388(2) ? C12 H11 . 0.942(17) ? C8 H8 . 0.952(17) ? C2 C1 . 1.375(3) ? C2 H2 . 0.951(19) ? C1 H1 . 0.966(18) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F1 C11 C10 118.91(15) . . ? F1 C11 C12 117.90(15) . . ? C10 C11 C12 123.19(15) . . ? C10 C9 C8 120.64(16) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C5 N1 C1 117.54(15) . . ? C14 O3 H12 111.8(13) . . ? C11 C10 C9 118.28(17) . . ? C11 C10 H10 121.0(10) . . ? C9 C10 H10 120.7(10) . . ? O1 C6 C7 121.29(17) . . ? O1 C6 C3 119.62(16) . . ? C7 C6 C3 119.09(15) . . ? C5 C4 C3 119.24(15) . . ? C5 C4 H3 119.4(10) . . ? C3 C4 H3 121.3(10) . . ? N1 C5 C4 123.09(16) . . ? N1 C5 H4 116.3(10) . . ? C4 C5 H4 120.6(10) . . ? C8 C13 C12 120.01(15) . . ? C8 C13 C14 121.59(14) . . ? C12 C13 C14 118.41(14) . . ? C6 C7 H7 107.6(15) . . ? C6 C7 H5 112.3(13) . . ? H7 C7 H5 107(2) . . ? C6 C7 H6 111.5(15) . . ? H7 C7 H6 109(2) . . ? H5 C7 H6 109.2(19) . . ? C4 C3 C2 117.67(15) . . ? C4 C3 C6 122.46(14) . . ? C2 C3 C6 119.87(15) . . ? C11 C12 C13 118.13(15) . . ? C11 C12 H11 120.5(10) . . ? C13 C12 H11 121.2(10) . . ? C13 C8 C9 119.75(16) . . ? C13 C8 H8 120.8(10) . . ? C9 C8 H8 119.5(10) . . ? C1 C2 C3 119.62(16) . . ? C1 C2 H2 119.1(11) . . ? C3 C2 H2 121.2(11) . . ? O2 C14 O3 123.58(16) . . ? O2 C14 C13 122.80(14) . . ? O3 C14 C13 113.62(14) . . ? N1 C1 C2 122.82(16) . . ? N1 C1 H1 114.6(11) . . ? C2 C1 H1 122.5(11) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F1 C11 C10 C9 -179.68(16) . . . . ? C12 C11 C10 C9 0.2(3) . . . . ? C8 C9 C10 C11 0.4(3) . . . . ? C1 N1 C5 C4 0.6(3) . . . . ? C3 C4 C5 N1 0.0(3) . . . . ? C5 C4 C3 C2 -1.1(2) . . . . ? C5 C4 C3 C6 179.30(15) . . . . ? O1 C6 C3 C4 -178.54(15) . . . . ? C7 C6 C3 C4 1.5(2) . . . . ? O1 C6 C3 C2 1.9(2) . . . . ? C7 C6 C3 C2 -178.05(17) . . . . ? F1 C11 C12 C13 179.33(14) . . . . ? C10 C11 C12 C13 -0.5(3) . . . . ? C8 C13 C12 C11 0.3(2) . . . . ? C14 C13 C12 C11 -179.71(14) . . . . ? C12 C13 C8 C9 0.2(2) . . . . ? C14 C13 C8 C9 -179.79(15) . . . . ? C10 C9 C8 C13 -0.5(3) . . . . ? C4 C3 C2 C1 1.7(2) . . . . ? C6 C3 C2 C1 -178.73(15) . . . . ? C8 C13 C14 O2 -176.67(15) . . . . ? C12 C13 C14 O2 3.4(2) . . . . ? C8 C13 C14 O3 3.1(2) . . . . ? C12 C13 C14 O3 -176.82(14) . . . . ? C5 N1 C1 C2 0.0(3) . . . . ? C3 C2 C1 N1 -1.2(3) . . . . ? 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_site_symmetry_A O3 H12 N1 1.02(3) 1.63(3) 2.6486(18) 177(2) . # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF # Attachment '- Xray_formII.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2010-02-09 at 12:53:59 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.4 # Request file : c:\wingx old2\files\acta.reqdat # CIF files read : cocrystal100k acta_c_original cocrystal100k #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_cocrystal100k _database_code_depnum_ccdc_archive 'CCDC 810546' #TrackingRef '- Xray_formII.cif' _audit_creation_date 2010-02-09T12:53:59-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; 3-fluorobenzoic acid 4-acetylpyridine ; _chemical_formula_moiety 'C7 H7 N O, C7 H5 F O2' _chemical_formula_sum 'C14 H12 F N O3' _chemical_formula_weight 261.25 #============================================================================== # CRYSTAL DATA _symmetry_space_group_name_H-M P21/n _symmetry_cell_setting monoclinic 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' _cell_length_a 7.9200(11) _cell_length_b 6.9633(9) _cell_length_c 21.918(4) _cell_angle_alpha 90 _cell_angle_beta 95.337(5) _cell_angle_gamma 90 _cell_volume 1203.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8295 _cell_measurement_theta_max 55.17 _cell_measurement_theta_min 6.14 _exptl_crystal_density_diffrn 1.442 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6888 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'CrystalClear 1.4.0 (Rigaku, 2008)' #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID IP Image Plate diffractometer' _diffrn_reflns_number 14143 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_unetI/netI 0.0301 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 #============================================================================== # STRUCTURE SOLUTION _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 2746 _reflns_number_gt 1952 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1084 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_number_reflns 2746 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment refall _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0528P)^2^+0.2271P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.281 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.048 _refine_ls_extinction_method none 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 0 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 1.24600(14) -0.54137(16) 0.17352(5) 0.0291(3) Uani d . 1 . . O N1 0.94012(15) 0.08453(18) 0.14907(5) 0.0232(3) Uani d . 1 . . N C1 1.03296(19) -0.0004(2) 0.19593(7) 0.0238(3) Uani d . 1 . . C C2 1.10673(18) -0.1787(2) 0.19088(7) 0.0221(3) Uani d . 1 . . C C3 1.08694(17) -0.2734(2) 0.13475(6) 0.0210(3) Uani d . 1 . . C C4 0.99241(19) -0.1852(2) 0.08607(7) 0.0230(3) Uani d . 1 . . C C5 0.92025(19) -0.0072(2) 0.09515(7) 0.0233(3) Uani d . 1 . . C C6 1.16812(18) -0.4687(2) 0.12900(7) 0.0225(3) Uani d . 1 . . C C7 1.1485(2) -0.5650(2) 0.06760(7) 0.0259(3) Uani d . 1 . . C H1 1.048(2) 0.067(2) 0.2329(7) 0.022(4) Uiso d . 1 . . H H2 1.171(2) -0.234(2) 0.2262(7) 0.026(4) Uiso d . 1 . . H H3 0.971(2) -0.244(2) 0.0459(8) 0.023(4) Uiso d . 1 . . H H4 0.853(2) 0.056(2) 0.0636(8) 0.028(4) Uiso d . 1 . . H H5 1.191(2) -0.484(3) 0.0362(9) 0.040(5) Uiso d . 1 . . H H6 1.026(2) -0.586(3) 0.0542(8) 0.034(5) Uiso d . 1 . . H H7 1.208(3) -0.686(3) 0.0695(9) 0.046(6) Uiso d . 1 . . H O2 0.69256(15) 0.39813(16) 0.06512(5) 0.0295(3) Uani d . 1 . . O O3 0.78143(14) 0.40819(16) 0.16528(5) 0.0276(3) Uani d . 1 . . O F1 0.34716(11) 1.00632(14) 0.03576(4) 0.0310(2) Uani d . 1 . . F C8 0.63198(18) 0.7588(2) 0.18094(7) 0.0223(3) Uani d . 1 . . C C9 0.55548(19) 0.9362(2) 0.18806(7) 0.0249(3) Uani d . 1 . . C C10 0.46045(19) 1.0213(2) 0.13893(7) 0.0246(3) Uani d . 1 . . C C11 0.44357(18) 0.9247(2) 0.08372(6) 0.0242(3) Uani d . 1 . . C C12 0.51668(18) 0.7489(2) 0.07469(7) 0.0221(3) Uani d . 1 . . C C13 0.61316(18) 0.6652(2) 0.12441(6) 0.0209(3) Uani d . 1 . . C C14 0.69773(18) 0.4771(2) 0.11495(6) 0.0221(3) Uani d . 1 . . C H8 0.700(2) 0.700(2) 0.2150(7) 0.021(4) Uiso d . 1 . . H H9 0.5682(19) 1.002(2) 0.2277(7) 0.019(4) Uiso d . 1 . . H H10 0.408(2) 1.143(3) 0.1437(7) 0.023(4) Uiso d . 1 . . H H11 0.504(2) 0.686(2) 0.0357(7) 0.023(4) Uiso d . 1 . . H H12 0.842(3) 0.284(4) 0.1574(11) 0.085(8) Uiso d . 1 . . H 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 O1 0.0335(6) 0.0280(6) 0.0243(5) 0.0066(5) -0.0047(4) 0.0013(5) N1 0.0225(6) 0.0211(6) 0.0255(6) -0.0007(5) 0.0003(5) 0.0003(5) C1 0.0232(7) 0.0249(8) 0.0231(7) -0.0017(6) 0.0003(6) -0.0034(6) C2 0.0207(7) 0.0244(8) 0.0206(7) -0.0003(6) -0.0014(5) 0.0009(6) C3 0.0201(7) 0.0210(7) 0.0218(7) -0.0015(6) 0.0018(5) 0.0007(6) C4 0.0242(8) 0.0233(8) 0.0210(7) -0.0010(6) -0.0004(6) -0.0006(6) C5 0.0237(7) 0.0230(8) 0.0224(7) -0.0013(6) -0.0020(6) 0.0030(6) C6 0.0202(7) 0.0236(8) 0.0233(7) 0.0000(6) 0.0005(5) 0.0001(6) C7 0.0294(8) 0.0251(8) 0.0223(7) 0.0048(7) -0.0015(6) -0.0011(6) O2 0.0374(6) 0.0283(6) 0.0224(5) 0.0056(5) -0.0001(4) -0.0020(4) O3 0.0350(6) 0.0231(6) 0.0236(5) 0.0059(5) -0.0032(4) -0.0004(4) F1 0.0319(5) 0.0344(5) 0.0254(5) 0.0099(4) -0.0035(4) 0.0042(4) C8 0.0209(7) 0.0249(8) 0.0206(7) -0.0002(6) -0.0003(5) 0.0028(6) C9 0.0235(7) 0.0274(8) 0.0238(7) -0.0006(6) 0.0017(6) -0.0025(6) C10 0.0234(7) 0.0212(8) 0.0291(8) 0.0029(6) 0.0029(6) 0.0013(6) C11 0.0198(7) 0.0291(8) 0.0230(7) 0.0010(6) -0.0016(5) 0.0059(6) C12 0.0216(7) 0.0234(8) 0.0212(7) -0.0015(6) 0.0019(6) 0.0009(6) C13 0.0199(7) 0.0211(7) 0.0220(7) -0.0021(6) 0.0030(5) 0.0014(6) C14 0.0222(7) 0.0221(8) 0.0219(7) -0.0019(6) 0.0016(5) 0.0015(6) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C6 . 1.2153(17) ? N1 C5 . 1.3398(19) ? N1 C1 . 1.3434(19) ? C1 C2 . 1.381(2) ? C1 H1 . 0.934(16) ? C2 C3 . 1.392(2) ? C2 H2 . 0.966(17) ? C3 C4 . 1.388(2) ? C3 C6 . 1.514(2) ? C4 C5 . 1.387(2) ? C4 H3 . 0.973(17) ? C5 H4 . 0.941(18) ? C6 C7 . 1.499(2) ? C7 H5 . 0.97(2) ? C7 H6 . 1.000(19) ? C7 H7 . 0.96(2) ? O2 C14 . 1.2200(17) ? O3 C14 . 1.3230(17) ? O3 H12 . 1.01(3) ? F1 C11 . 1.3642(16) ? C8 C9 . 1.391(2) ? C8 C13 . 1.396(2) ? C8 H8 . 0.970(16) ? C9 C10 . 1.388(2) ? C9 H9 . 0.979(15) ? C10 C11 . 1.380(2) ? C10 H10 . 0.954(18) ? C11 C12 . 1.376(2) ? C12 C13 . 1.399(2) ? C12 H11 . 0.957(16) ? C13 C14 . 1.494(2) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C1 118.38(13) . . ? N1 C1 C2 122.70(14) . . ? N1 C1 H1 117.2(10) . . ? C2 C1 H1 120.1(10) . . ? C1 C2 C3 118.90(13) . . ? C1 C2 H2 119.2(10) . . ? C3 C2 H2 121.9(10) . . ? C4 C3 C2 118.55(14) . . ? C4 C3 C6 122.41(13) . . ? C2 C3 C6 119.04(12) . . ? C5 C4 C3 119.01(14) . . ? C5 C4 H3 118.0(10) . . ? C3 C4 H3 122.9(10) . . ? N1 C5 C4 122.46(14) . . ? N1 C5 H4 115.9(10) . . ? C4 C5 H4 121.6(10) . . ? O1 C6 C7 122.47(14) . . ? O1 C6 C3 119.67(13) . . ? C7 C6 C3 117.87(12) . . ? C6 C7 H5 111.2(11) . . ? C6 C7 H6 110.3(10) . . ? H5 C7 H6 105.7(15) . . ? C6 C7 H7 110.1(12) . . ? H5 C7 H7 109.7(16) . . ? H6 C7 H7 109.8(16) . . ? C14 O3 H12 112.1(14) . . ? C9 C8 C13 120.19(13) . . ? C9 C8 H8 120.3(9) . . ? C13 C8 H8 119.5(9) . . ? C10 C9 C8 120.16(14) . . ? C10 C9 H9 119.4(9) . . ? C8 C9 H9 120.4(9) . . ? C11 C10 C9 118.29(14) . . ? C11 C10 H10 121.4(10) . . ? C9 C10 H10 120.3(10) . . ? F1 C11 C12 118.19(13) . . ? F1 C11 C10 118.33(13) . . ? C12 C11 C10 123.47(13) . . ? C11 C12 C13 117.74(14) . . ? C11 C12 H11 121.6(10) . . ? C13 C12 H11 120.6(10) . . ? C8 C13 C12 120.15(14) . . ? C8 C13 C14 121.35(13) . . ? C12 C13 C14 118.48(13) . . ? O2 C14 O3 123.74(14) . . ? O2 C14 C13 122.75(13) . . ? O3 C14 C13 113.49(12) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 -0.7(2) . . . . ? N1 C1 C2 C3 1.1(2) . . . . ? C1 C2 C3 C4 -0.5(2) . . . . ? C1 C2 C3 C6 179.82(13) . . . . ? C2 C3 C4 C5 -0.5(2) . . . . ? C6 C3 C4 C5 179.21(13) . . . . ? C1 N1 C5 C4 -0.3(2) . . . . ? C3 C4 C5 N1 0.9(2) . . . . ? C4 C3 C6 O1 -178.15(14) . . . . ? C2 C3 C6 O1 1.5(2) . . . . ? C4 C3 C6 C7 1.9(2) . . . . ? C2 C3 C6 C7 -178.43(13) . . . . ? C13 C8 C9 C10 -0.2(2) . . . . ? C8 C9 C10 C11 0.5(2) . . . . ? C9 C10 C11 F1 178.60(13) . . . . ? C9 C10 C11 C12 -0.3(2) . . . . ? F1 C11 C12 C13 -179.06(13) . . . . ? C10 C11 C12 C13 -0.1(2) . . . . ? C9 C8 C13 C12 -0.3(2) . . . . ? C9 C8 C13 C14 178.33(13) . . . . ? C11 C12 C13 C8 0.4(2) . . . . ? C11 C12 C13 C14 -178.21(13) . . . . ? C8 C13 C14 O2 -175.12(14) . . . . ? C12 C13 C14 O2 3.5(2) . . . . ? C8 C13 C14 O3 3.3(2) . . . . ? C12 C13 C14 O3 -178.13(13) . . . . ? 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_site_symmetry_A O3 H12 N1 1.01(3) 1.61(3) 2.6207(17) 177(2) . data_cocrystal200K _database_code_depnum_ccdc_archive 'CCDC 810547' #TrackingRef '- Xray_formII.cif' _audit_creation_date 2010-02-09T13:11:30-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C7 H7 N O, C7 H5 F O2' _chemical_formula_sum 'C14 H12 F N O3' _chemical_formula_weight 261.25 #============================================================================== # CRYSTAL DATA _symmetry_space_group_name_H-M P21/n _symmetry_cell_setting monoclinic 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' _cell_length_a 8.0544(12) _cell_length_b 6.9420(10) _cell_length_c 22.058(4) _cell_angle_alpha 90 _cell_angle_beta 95.990(7) _cell_angle_gamma 90 _cell_volume 1226.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 5254 _cell_measurement_theta_max 55.11 _cell_measurement_theta_min 6.16 _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.11 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6465 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'CrystalClear 1.4.0 (Rigaku, 2008)' #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID IP Image Plate diffractometer' _diffrn_reflns_number 13397 _diffrn_reflns_av_R_equivalents 0.0449 _diffrn_reflns_av_unetI/netI 0.0351 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measured_fraction_theta_full 0.992 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 #============================================================================== # STRUCTURE SOLUTION _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 2780 _reflns_number_gt 1676 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.087 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1314 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_number_reflns 2780 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment refall _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0629P)^2^+0.1120P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.2 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.041 _refine_ls_extinction_method none 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 0 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 1.24502(19) -0.5373(2) 0.17343(6) 0.0527(4) Uani d . 1 . . O N1 0.93829(19) 0.0857(2) 0.14900(7) 0.0406(4) Uani d . 1 . . N C1 1.0319(2) 0.0014(3) 0.19532(9) 0.0411(5) Uani d . 1 . . C C2 1.1056(2) -0.1760(3) 0.19047(8) 0.0385(4) Uani d . 1 . . C C3 1.0864(2) -0.2709(3) 0.13474(8) 0.0350(4) Uani d . 1 . . C C4 0.9909(2) -0.1833(3) 0.08655(9) 0.0392(4) Uani d . 1 . . C C5 0.9189(2) -0.0064(3) 0.09547(8) 0.0407(5) Uani d . 1 . . C C6 1.1680(2) -0.4648(3) 0.12891(8) 0.0387(4) Uani d . 1 . . C C7 1.1507(3) -0.5607(3) 0.06816(9) 0.0473(5) Uani d . 1 . . C H1 1.043(3) 0.069(3) 0.2326(9) 0.051(6) Uiso d . 1 . . H H2 1.174(3) -0.230(3) 0.2256(9) 0.052(6) Uiso d . 1 . . H H3 0.972(2) -0.244(3) 0.0456(9) 0.047(5) Uiso d . 1 . . H H4 0.850(3) 0.057(3) 0.0628(9) 0.047(5) Uiso d . 1 . . H H5 1.188(3) -0.479(3) 0.0371(11) 0.066(7) Uiso d . 1 . . H H6 1.029(3) -0.583(3) 0.0541(9) 0.054(6) Uiso d . 1 . . H H7 1.212(3) -0.682(4) 0.0697(11) 0.079(8) Uiso d . 1 . . H O2 0.6927(2) 0.4013(2) 0.06541(6) 0.0538(4) Uani d . 1 . . O O3 0.77987(19) 0.4094(2) 0.16482(6) 0.0485(4) Uani d . 1 . . O F1 0.34712(15) 1.00638(18) 0.03658(5) 0.0574(4) Uani d . 1 . . F C8 0.6313(2) 0.7590(3) 0.18076(8) 0.0384(4) Uani d . 1 . . C C9 0.5550(2) 0.9353(3) 0.18793(9) 0.0431(5) Uani d . 1 . . C C10 0.4601(2) 1.0197(3) 0.13931(9) 0.0428(5) Uani d . 1 . . C C11 0.4435(2) 0.9246(3) 0.08436(8) 0.0413(5) Uani d . 1 . . C C12 0.5173(2) 0.7497(3) 0.07500(9) 0.0383(4) Uani d . 1 . . C C13 0.6130(2) 0.6665(3) 0.12437(8) 0.0352(4) Uani d . 1 . . C C14 0.6973(2) 0.4792(3) 0.11496(8) 0.0380(4) Uani d . 1 . . C H8 0.701(2) 0.699(3) 0.2146(9) 0.041(5) Uiso d . 1 . . H H9 0.566(2) 1.000(3) 0.2282(9) 0.050(6) Uiso d . 1 . . H H10 0.406(2) 1.137(3) 0.1441(8) 0.045(6) Uiso d . 1 . . H H11 0.501(2) 0.688(3) 0.0360(9) 0.050(6) Uiso d . 1 . . H H12 0.839(4) 0.288(5) 0.1562(13) 0.111(11) Uiso d . 1 . . H 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 O1 0.0637(10) 0.0475(9) 0.0436(8) 0.0142(7) -0.0103(7) 0.0006(6) N1 0.0408(9) 0.0362(9) 0.0437(9) 0.0008(7) -0.0011(7) 0.0003(7) C1 0.0400(10) 0.0421(11) 0.0402(10) 0.0008(9) -0.0003(8) -0.0049(8) C2 0.0374(10) 0.0424(11) 0.0347(10) 0.0013(8) -0.0017(8) 0.0005(8) C3 0.0335(9) 0.0347(10) 0.0363(9) -0.0011(8) 0.0011(7) 0.0012(7) C4 0.0429(11) 0.0377(11) 0.0355(10) 0.0001(8) -0.0025(8) -0.0001(8) C5 0.0445(11) 0.0375(11) 0.0382(10) -0.0001(9) -0.0039(8) 0.0043(8) C6 0.0376(10) 0.0378(11) 0.0395(10) -0.0001(8) -0.0011(8) 0.0009(8) C7 0.0563(14) 0.0452(13) 0.0387(11) 0.0108(11) -0.0028(9) -0.0029(9) O2 0.0712(10) 0.0500(9) 0.0387(8) 0.0121(8) -0.0013(7) -0.0045(6) O3 0.0630(9) 0.0389(8) 0.0410(7) 0.0121(7) -0.0076(6) -0.0014(6) F1 0.0612(8) 0.0622(8) 0.0462(7) 0.0211(6) -0.0069(5) 0.0075(6) C8 0.0377(10) 0.0404(11) 0.0361(10) -0.0014(9) -0.0004(8) 0.0034(8) C9 0.0427(11) 0.0442(12) 0.0420(11) 0.0004(9) 0.0026(8) -0.0038(9) C10 0.0399(11) 0.0387(12) 0.0496(12) 0.0084(9) 0.0041(8) 0.0015(9) C11 0.0359(10) 0.0483(12) 0.0388(10) 0.0042(9) -0.0002(8) 0.0096(8) C12 0.0371(10) 0.0408(11) 0.0363(10) 0.0006(9) 0.0013(8) 0.0017(8) C13 0.0349(9) 0.0345(10) 0.0361(9) -0.0017(8) 0.0037(7) 0.0028(7) C14 0.0400(10) 0.0365(10) 0.0370(10) -0.0005(8) 0.0012(8) 0.0036(8) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C6 . 1.215(2) ? N1 C5 . 1.337(2) ? N1 C1 . 1.340(2) ? C1 C2 . 1.376(3) ? C1 H1 . 0.94(2) ? C2 C3 . 1.389(2) ? C2 H2 . 0.98(2) ? C3 C4 . 1.386(2) ? C3 C6 . 1.510(3) ? C4 C5 . 1.381(3) ? C4 H3 . 0.99(2) ? C5 H4 . 0.97(2) ? C6 C7 . 1.490(3) ? C7 H5 . 0.96(2) ? C7 H6 . 1.01(2) ? C7 H7 . 0.97(3) ? O2 C14 . 1.216(2) ? O3 C14 . 1.317(2) ? O3 H12 . 0.99(3) ? F1 C11 . 1.366(2) ? C8 C9 . 1.386(3) ? C8 C13 . 1.394(3) ? C8 H8 . 0.978(19) ? C9 C10 . 1.381(3) ? C9 H9 . 0.99(2) ? C10 C11 . 1.375(3) ? C10 H10 . 0.93(2) ? C11 C12 . 1.377(3) ? C12 C13 . 1.392(2) ? C12 H11 . 0.96(2) ? C13 C14 . 1.491(3) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C1 117.96(17) . . ? N1 C1 C2 123.01(18) . . ? N1 C1 H1 116.2(13) . . ? C2 C1 H1 120.7(13) . . ? C1 C2 C3 118.95(17) . . ? C1 C2 H2 119.6(12) . . ? C3 C2 H2 121.4(12) . . ? C4 C3 C2 118.19(18) . . ? C4 C3 C6 122.52(16) . . ? C2 C3 C6 119.28(16) . . ? C5 C4 C3 119.25(18) . . ? C5 C4 H3 118.5(12) . . ? C3 C4 H3 122.2(12) . . ? N1 C5 C4 122.61(18) . . ? N1 C5 H4 116.4(12) . . ? C4 C5 H4 121.0(12) . . ? O1 C6 C7 122.31(18) . . ? O1 C6 C3 119.38(16) . . ? C7 C6 C3 118.32(16) . . ? C6 C7 H5 111.7(14) . . ? C6 C7 H6 110.0(12) . . ? H5 C7 H6 103.5(18) . . ? C6 C7 H7 110.8(14) . . ? H5 C7 H7 110(2) . . ? H6 C7 H7 110.4(19) . . ? C14 O3 H12 111.1(16) . . ? C9 C8 C13 120.11(18) . . ? C9 C8 H8 120.8(11) . . ? C13 C8 H8 119.0(11) . . ? C10 C9 C8 120.14(19) . . ? C10 C9 H9 119.7(12) . . ? C8 C9 H9 120.1(12) . . ? C11 C10 C9 118.45(19) . . ? C11 C10 H10 120.9(12) . . ? C9 C10 H10 120.6(12) . . ? F1 C11 C10 118.43(18) . . ? F1 C11 C12 118.08(17) . . ? C10 C11 C12 123.49(17) . . ? C11 C12 C13 117.46(17) . . ? C11 C12 H11 120.5(12) . . ? C13 C12 H11 122.0(12) . . ? C12 C13 C8 120.35(18) . . ? C12 C13 C14 118.41(16) . . ? C8 C13 C14 121.22(16) . . ? O2 C14 O3 123.53(18) . . ? O2 C14 C13 122.73(17) . . ? O3 C14 C13 113.72(16) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 -1.3(3) . . . . ? N1 C1 C2 C3 1.8(3) . . . . ? C1 C2 C3 C4 -1.1(3) . . . . ? C1 C2 C3 C6 179.51(17) . . . . ? C2 C3 C4 C5 0.0(3) . . . . ? C6 C3 C4 C5 179.43(17) . . . . ? C1 N1 C5 C4 0.1(3) . . . . ? C3 C4 C5 N1 0.5(3) . . . . ? C4 C3 C6 O1 -177.27(18) . . . . ? C2 C3 C6 O1 2.1(3) . . . . ? C4 C3 C6 C7 2.7(3) . . . . ? C2 C3 C6 C7 -177.89(18) . . . . ? C13 C8 C9 C10 0.2(3) . . . . ? C8 C9 C10 C11 0.2(3) . . . . ? C9 C10 C11 F1 178.82(17) . . . . ? C9 C10 C11 C12 -0.4(3) . . . . ? F1 C11 C12 C13 -178.99(16) . . . . ? C10 C11 C12 C13 0.3(3) . . . . ? C11 C12 C13 C8 0.1(3) . . . . ? C11 C12 C13 C14 -178.64(16) . . . . ? C9 C8 C13 C12 -0.3(3) . . . . ? C9 C8 C13 C14 178.40(17) . . . . ? C12 C13 C14 O2 3.7(3) . . . . ? C8 C13 C14 O2 -175.03(18) . . . . ? C12 C13 C14 O3 -177.80(16) . . . . ? C8 C13 C14 O3 3.4(2) . . . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF # Attachment '- neutron_formI.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2010-02-09 at 16:59:43 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.4 # Request file : c:\wingx old2\files\acta.reqdat # CIF files read : fpa30d #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_fpa30d _database_code_depnum_ccdc_archive 'CCDC 810548' #TrackingRef '- neutron_formI.cif' _audit_creation_date 2010-02-09T16:59:43-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_formula_sum 'C14 H12 F N O3' _chemical_formula_weight 261.25 #============================================================================== # CRYSTAL DATA 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' _symmetry_space_group_name_H-M P21/n _symmetry_cell_setting monoclinic _cell_length_a 10.046(2) _cell_length_b 10.573(2) _cell_length_c 11.461(2) _cell_angle_alpha 90 _cell_angle_beta 91.16(2) _cell_angle_gamma 90 _cell_volume 1217.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 30(2) _exptl_crystal_size_max 8 _exptl_crystal_size_mid 4 _exptl_crystal_size_min 2 _exptl_crystal_density_diffrn 1.426 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 322 _exptl_absorpt_coefficient_mu 0.135 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details 'SXD2001 (Gutmann, 2001)' #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; For peak integration a local UB matrix refined for each frame, using approximately 100 reflections from each of the 11 detectors. Hence _cell_measurement_reflns_used 1000 For final cell dimensions a weighted average of all local cells from each frame was calculated. 5 frames of data were collected Because of the nature of the experiment, it is not possible to give values of theta_min and theta_max for the cell determination. The same applies for the wavelength used for the experiment. The range of wavelengths used was 0.7-6.9 Angstroms, BUT the bulk of the diffraction information is obtained from wavelengths in the range 0.8-2.9 Angstroms. The data collection procedures on the SXD instrument used for the single crystal neutron data collection are most recently summarised the following paper D. A. Keen, M. J. Gutmann and C. C. Wilson, J. Appl. Cryst., 2006, 39, 714. ; _diffrn_ambient_temperature 30(2) _diffrn_radiation_wavelength 0.7-6.9 _diffrn_radiation_probe neutron _diffrn_radiation_type neutron _diffrn_radiation_source 'ISIS spallation source' _diffrn_measurement_device_type 'SXD time-of-flight LAUE diffraction' _diffrn_measurement_method 'time-of-flight LAUE diffraction' _diffrn_reflns_number 14476 _diffrn_reflns_av_unetI/netI 0.0559 _diffrn_reflns_theta_min 8.73 _diffrn_reflns_theta_max 83.53 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 26 #============================================================================== # STRUCTURE SOLUTION _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap #============================================================================== # REFINEMENT DATA _refine_special_details ; The variable wavelength nature of the data collection procedure means that sensible values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max cannot be given instead the following limits are given _diffrn_reflns_sin(theta)/lambda_min 0.04 _diffrn_reflns_sin(theta)/lambda_max 1.39 _refine_diff_density_max/min is given in Fermi per per angstrom cubed not electons per angstrom cubed. Another way to consider the _refine_diff_density_ is as a percentage of the diffracted intensity of a given atom: _refine_diff_density_max = 10% of Carbon _refine_diff_density_min = -8% of Carbon Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 14476 _reflns_number_gt 14476 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0743 _refine_ls_R_factor_gt 0.0743 _refine_ls_wR_factor_ref 0.1865 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_number_reflns 14476 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment refall _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1028P)^2^+38.8563P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 2.786 _refine_diff_density_min -2.324 _refine_diff_density_rms 0.516 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0371(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'SXD2001 (Gutmann, 2001)' _computing_cell_refinement 'SXD2001 (Gutmann, 2001)' _computing_data_reduction 'SXD2001 (Gutmann, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group H11 H 0.6292(3) 0.92581(19) 0.5023(3) 0.0224(6) Uani 1 1 d . . . H8 H 0.6121(3) 0.5257(2) 0.5778(3) 0.0227(6) Uani 1 1 d . . . H4 H 0.1421(3) 0.4884(2) 0.7281(3) 0.0237(6) Uani 1 1 d . . . H7 H -0.2764(5) 0.6058(4) 0.9435(3) 0.0358(10) Uani 1 1 d . . . H3 H -0.0863(3) 0.5118(2) 0.7964(3) 0.0228(6) Uani 1 1 d . . . H2 H -0.0466(4) 0.91554(19) 0.7469(3) 0.0247(6) Uani 1 1 d . . . H10 H 0.9647(4) 0.6874(3) 0.4319(3) 0.0255(6) Uani 1 1 d . . . H1 H 0.1812(3) 0.8732(2) 0.6737(3) 0.0236(6) Uani 1 1 d . . . H5 H -0.2914(4) 0.5456(3) 0.8010(4) 0.0315(8) Uani 1 1 d . . . H6 H -0.4120(4) 0.6533(3) 0.8506(4) 0.0338(8) Uani 1 1 d . . . H12 H 0.3186(3) 0.6612(2) 0.6582(3) 0.0187(5) Uani 1 1 d . . . O2 O 0.41302(14) 0.84855(9) 0.58270(12) 0.0095(2) Uani 1 1 d . . . O1 O -0.26998(15) 0.84792(9) 0.81766(13) 0.0122(3) Uani 1 1 d . . . F1 F 0.86850(16) 0.91555(10) 0.42372(14) 0.0122(2) Uani 1 1 d . . . C11 C 0.80228(12) 0.81430(7) 0.46489(10) 0.00759(18) Uani 1 1 d . . . C9 C 0.79483(12) 0.59239(7) 0.50571(10) 0.00799(18) Uani 1 1 d . . . H9 H 0.8398(4) 0.4994(2) 0.5068(3) 0.0271(7) Uani 1 1 d . . . N1 N 0.16995(8) 0.67950(5) 0.69704(7) 0.00804(13) Uani 1 1 d . . . O3 O 0.41685(14) 0.64321(9) 0.63303(13) 0.0102(2) Uani 1 1 d . . . C10 C 0.86436(12) 0.69659(8) 0.46395(10) 0.00847(19) Uani 1 1 d . . . C6 C -0.22619(11) 0.74007(7) 0.81607(9) 0.00712(18) Uani 1 1 d . . . C4 C -0.03225(11) 0.59530(7) 0.77119(9) 0.00680(17) Uani 1 1 d . . . C5 C 0.09642(12) 0.58145(7) 0.73138(10) 0.00756(17) Uani 1 1 d . . . C13 C 0.60706(11) 0.72702(7) 0.54605(9) 0.00627(17) Uani 1 1 d . . . C7 C -0.30744(12) 0.62908(8) 0.85400(10) 0.00936(19) Uani 1 1 d . . . C3 C -0.08683(11) 0.71692(7) 0.77637(9) 0.00612(17) Uani 1 1 d . . . C12 C 0.67530(11) 0.83262(7) 0.50488(9) 0.00664(17) Uani 1 1 d . . . C8 C 0.66636(12) 0.60701(7) 0.54619(9) 0.00729(17) Uani 1 1 d . . . C2 C -0.00897(12) 0.81938(7) 0.74289(10) 0.00795(18) Uani 1 1 d . . . C14 C 0.46926(11) 0.74627(7) 0.58902(9) 0.00631(17) Uani 1 1 d . . . C1 C 0.11797(12) 0.79672(7) 0.70302(10) 0.00781(18) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 H11 0.0245(15) 0.0120(6) 0.0307(14) 0.0021(7) 0.0036(11) 0.0030(7) H8 0.0241(15) 0.0137(6) 0.0307(14) 0.0039(7) 0.0104(12) -0.0025(7) H4 0.0219(14) 0.0125(6) 0.0370(16) 0.0020(7) 0.0072(12) 0.0064(7) H7 0.045(3) 0.0424(15) 0.0204(15) 0.0131(12) -0.0014(16) -0.0120(15) H3 0.0219(14) 0.0122(6) 0.0346(15) 0.0038(7) 0.0075(11) -0.0036(7) H2 0.0257(15) 0.0105(6) 0.0383(16) 0.0011(7) 0.0056(12) 0.0035(7) H10 0.0177(14) 0.0236(9) 0.0356(17) 0.0015(9) 0.0108(13) 0.0038(8) H1 0.0205(14) 0.0168(7) 0.0338(15) 0.0045(8) 0.0085(12) -0.0058(8) H5 0.0297(18) 0.0194(9) 0.046(2) -0.0132(10) 0.0128(15) -0.0060(9) H6 0.0147(14) 0.0287(11) 0.058(3) 0.0056(13) 0.0083(15) 0.0018(10) H12 0.0133(11) 0.0184(7) 0.0248(13) 0.0022(7) 0.0086(10) -0.0012(7) O2 0.0083(5) 0.0066(2) 0.0137(5) 0.0008(3) 0.0049(4) 0.0019(3) O1 0.0108(6) 0.0061(2) 0.0196(6) -0.0006(3) 0.0021(5) 0.0024(3) F1 0.0107(6) 0.0083(3) 0.0179(6) 0.0023(3) 0.0055(5) -0.0014(3) C11 0.0082(4) 0.0062(2) 0.0085(4) 0.0008(2) 0.0024(3) 0.0000(2) C9 0.0086(4) 0.0061(2) 0.0093(4) 0.0011(2) 0.0029(3) 0.0015(2) H9 0.0280(17) 0.0139(7) 0.0398(17) 0.0039(8) 0.0068(13) 0.0072(8) N1 0.0071(3) 0.00718(15) 0.0099(3) 0.00119(16) 0.0023(2) -0.00020(16) O3 0.0079(5) 0.0068(3) 0.0159(6) 0.0024(3) 0.0042(4) -0.0003(3) C10 0.0080(5) 0.0077(2) 0.0098(4) 0.0009(2) 0.0026(4) 0.0009(2) C6 0.0069(4) 0.00537(19) 0.0091(4) -0.0007(2) 0.0003(3) 0.0007(2) C4 0.0074(4) 0.00469(19) 0.0083(4) -0.00019(19) 0.0017(3) 0.0001(2) C5 0.0073(4) 0.0056(2) 0.0099(4) 0.0002(2) 0.0023(3) 0.0008(2) C13 0.0074(4) 0.00471(19) 0.0068(4) 0.00002(19) 0.0008(3) 0.0001(2) C7 0.0071(4) 0.0080(2) 0.0131(5) 0.0005(2) 0.0036(4) -0.0001(2) C3 0.0058(4) 0.00475(19) 0.0078(4) -0.00016(19) 0.0009(3) 0.00025(19) C12 0.0071(4) 0.0056(2) 0.0073(4) 0.0001(2) 0.0025(3) -0.0003(2) C8 0.0091(4) 0.00504(19) 0.0078(4) 0.0008(2) 0.0024(3) 0.0004(2) C2 0.0072(4) 0.00482(19) 0.0119(4) 0.0005(2) 0.0016(3) -0.0004(2) C14 0.0063(4) 0.00537(19) 0.0073(4) -0.00057(19) 0.0018(3) 0.0005(2) C1 0.0078(4) 0.00586(19) 0.0098(4) 0.0008(2) 0.0024(3) -0.0010(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C14 1.2215(13) . ? O1 C6 1.2225(13) . ? F1 C11 1.3505(17) . ? C11 C12 1.3779(19) . ? C11 C10 1.3922(13) . ? C9 C8 1.3889(19) . ? C9 C10 1.3944(15) . ? N1 C5 1.3368(13) . ? N1 C1 1.3471(11) . ? O3 C14 1.3152(15) . ? C6 C7 1.4989(15) . ? C6 C3 1.5009(18) . ? C4 C5 1.3873(19) . ? C4 C3 1.3996(12) . ? C13 C12 1.3972(14) . ? C13 C8 1.4017(12) . ? C13 C14 1.4926(18) . ? C3 C2 1.3945(14) . ? C2 C1 1.3842(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F1 C11 C12 118.08(10) . . ? F1 C11 C10 118.81(13) . . ? C12 C11 C10 123.10(10) . . ? C8 C9 C10 120.14(8) . . ? C5 N1 C1 118.78(10) . . ? C11 C10 C9 118.43(12) . . ? O1 C6 C7 121.85(13) . . ? O1 C6 C3 119.66(12) . . ? C7 C6 C3 118.49(8) . . ? C5 C4 C3 118.64(9) . . ? N1 C5 C4 122.62(8) . . ? C12 C13 C8 120.82(11) . . ? C12 C13 C14 117.84(8) . . ? C8 C13 C14 121.34(9) . . ? C2 C3 C4 118.66(11) . . ? C2 C3 C6 119.24(8) . . ? C4 C3 C6 122.10(9) . . ? C11 C12 C13 117.64(8) . . ? C9 C8 C13 119.87(9) . . ? C1 C2 C3 118.81(8) . . ? O2 C14 O3 124.60(14) . . ? O2 C14 C13 122.15(11) . . ? O3 C14 C13 113.25(9) . . ? N1 C1 C2 122.46(9) . . ? 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_site_symmetry_A O3 H12 N1 1.051(4) 1.579(3) 2.6288(19) 176.6(2) . #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_fpa300d _database_code_depnum_ccdc_archive 'CCDC 810549' #TrackingRef '- neutron_formI.cif' _audit_creation_date 2010-02-10T12:26:21-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; 3-fluorobenzoic acid 4-acetylpyridine ; _chemical_formula_sum 'C14 H12 F N O3' _chemical_formula_weight 261.25 #============================================================================== # CRYSTAL DATA 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' _symmetry_space_group_name_H-M P21/n _symmetry_cell_setting monoclinic _cell_length_a 10.105(4) _cell_length_b 10.734(4) _cell_length_c 11.806(4) _cell_angle_alpha 90 _cell_angle_beta 91.08(3) _cell_angle_gamma 90 _cell_volume 1280.4(8) _cell_formula_units_Z 4 _cell_measurement_temperature 300(2) _exptl_crystal_size_max 8 _exptl_crystal_size_mid 4 _exptl_crystal_size_min 2 _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 322 _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details 'SXD2001 (Gutmann, 2001)' #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; For peak integration a local UB matrix refined for each frame, using approximately 100 reflections from each of the 11 detectors. Hence _cell_measurement_reflns_used 1000 For final cell dimensions a weighted average of all local cells from each frame was calculated. 5 frames of data were collected Because of the nature of the experiment, it is not possible to give values of theta_min and theta_max for the cell determination. The same applies for the wavelength used for the experiment. The range of wavelengths used was 0.7-6.9 Angstroms, BUT the bulk of the diffraction information is obtained from wavelengths in the range 0.8-2.9 Angstroms. The data collection procedures on the SXD instrument used for the single crystal neutron data collection are most recently summarised the following paper D. A. Keen, M. J. Gutmann and C. C. Wilson, J. Appl. Cryst., 2006, 39, 714. ; _diffrn_ambient_temperature 300(2) _diffrn_radiation_wavelength 0.7-6.9 _diffrn_radiation_probe neutron _diffrn_radiation_type neutron _diffrn_radiation_source 'ISIS spallation source' _diffrn_measurement_device_type 'SXD time-of-flight LAUE diffraction' _diffrn_measurement_method 'time-of-flight LAUE diffraction' _diffrn_reflns_number 3105 _diffrn_reflns_av_unetI/netI 0.0529 _diffrn_reflns_theta_min 8.8 _diffrn_reflns_theta_max 82.74 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 20 #============================================================================== # STRUCTURE SOLUTION _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #============================================================================== # REFINEMENT DATA _refine_special_details ; The variable wavelength nature of the data collection procedure means that sensible values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max cannot be given instead the following limits are given _diffrn_reflns_sin(theta)/lambda_min 0.09 _diffrn_reflns_sin(theta)/lambda_max 1.30 _refine_diff_density_max/min is given in Fermi per per angstrom cubed not electons per angstrom cubed. Another way to consider the _refine_diff_density_ is as a percentage of the diffracted intensity of a given atom: _refine_diff_density_max = 7.49% of Carbon _refine_diff_density_min = -4.32% of Carbon Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 3105 _reflns_number_gt 3105 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0952 _refine_ls_R_factor_gt 0.0952 _refine_ls_wR_factor_ref 0.2415 _refine_ls_goodness_of_fit_ref 1.141 _refine_ls_restrained_S_all 1.141 _refine_ls_number_reflns 3105 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment refall _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1600P)^2^+16.8532P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.656 _refine_diff_density_min -0.664 _refine_diff_density_rms 0.16 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.058(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'SXD2001 (Gutmann, 2001)' _computing_cell_refinement 'SXD2001 (Gutmann, 2001)' _computing_data_reduction 'SXD2001 (Gutmann, 2001)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol H11 0.6297(13) 0.9232(9) 0.5023(11) 0.083(4) Uani d . 1 . . H H8 0.6070(13) 0.5324(10) 0.5752(11) 0.083(4) Uani d . 1 . . H H4 0.1408(14) 0.4990(11) 0.7260(13) 0.101(4) Uani d . 1 . . H H7 -0.268(2) 0.606(2) 0.935(2) 0.171(11) Uani d . 1 . . H H3 -0.0884(14) 0.5204(10) 0.7952(13) 0.093(4) Uani d . 1 . . H H2 -0.0480(16) 0.9163(11) 0.7455(14) 0.100(5) Uani d . 1 . . H H10 0.9608(18) 0.6851(13) 0.4332(14) 0.098(4) Uani d . 1 . . H H1 0.1760(15) 0.8760(14) 0.6751(14) 0.106(5) Uani d . 1 . . H H5 -0.300(2) 0.5608(18) 0.807(2) 0.140(8) Uani d . 1 . . H H6 -0.402(2) 0.659(2) 0.861(3) 0.176(11) Uani d . 1 . . H H12 0.3168(15) 0.6679(11) 0.6545(11) 0.079(3) Uani d . 1 . . H O2 0.4164(7) 0.8524(6) 0.5856(7) 0.078(2) Uani d . 1 . . O O1 -0.2694(9) 0.8499(6) 0.8146(8) 0.091(3) Uani d . 1 . . O F1 0.8687(10) 0.9103(7) 0.4250(10) 0.106(3) Uani d . 1 . . F C11 0.8008(6) 0.8117(4) 0.4636(5) 0.0584(15) Uani d . 1 . . C C9 0.7892(6) 0.5950(5) 0.5040(5) 0.0613(16) Uani d . 1 . . C H9 0.8300(16) 0.5032(12) 0.5030(13) 0.107(5) Uani d . 1 . . H N1 0.1665(4) 0.6865(4) 0.6955(4) 0.0621(12) Uani d . 1 . . N O3 0.4131(10) 0.6489(6) 0.6292(8) 0.083(2) Uani d . 1 . . O C10 0.8606(8) 0.6948(5) 0.4631(5) 0.0654(16) Uani d . 1 . . C C6 -0.2249(5) 0.7447(5) 0.8162(4) 0.0544(13) Uani d . 1 . . C C4 -0.0324(6) 0.6032(4) 0.7697(4) 0.0503(14) Uani d . 1 . . C C5 0.0940(6) 0.5900(4) 0.7289(5) 0.0563(14) Uani d . 1 . . C C13 0.6056(5) 0.7296(4) 0.5447(4) 0.0453(12) Uani d . 1 . . C C7 -0.3047(8) 0.6357(7) 0.8555(7) 0.0716(18) Uani d . 1 . . C C3 -0.0877(5) 0.7218(4) 0.7747(4) 0.0481(13) Uani d . 1 . . C C12 0.6744(6) 0.8312(5) 0.5041(4) 0.0528(14) Uani d . 1 . . C C8 0.6618(6) 0.6113(5) 0.5449(5) 0.0547(15) Uani d . 1 . . C C2 -0.0111(6) 0.8230(5) 0.7415(5) 0.0580(15) Uani d . 1 . . C C14 0.4694(5) 0.7502(5) 0.5879(4) 0.0514(13) Uani d . 1 . . C C1 0.1145(7) 0.8001(5) 0.7012(5) 0.0619(16) Uani d . 1 . . C 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 H11 0.084(9) 0.042(5) 0.124(11) -0.003(5) 0.020(7) 0.010(5) H8 0.076(9) 0.055(5) 0.120(11) -0.005(5) 0.030(7) 0.014(6) H4 0.085(10) 0.060(6) 0.161(14) 0.023(6) 0.034(8) 0.005(7) H7 0.14(2) 0.178(19) 0.19(2) -0.044(14) -0.023(19) 0.083(18) H3 0.082(10) 0.057(6) 0.141(12) -0.019(6) 0.052(8) 0.003(6) H2 0.103(11) 0.051(7) 0.146(13) 0.000(6) 0.013(9) 0.000(7) H10 0.066(11) 0.107(10) 0.121(12) 0.019(7) 0.030(9) 0.013(8) H1 0.079(10) 0.078(8) 0.162(14) -0.026(7) 0.037(9) 0.029(8) H5 0.110(15) 0.105(11) 0.21(2) -0.059(11) 0.044(14) -0.036(13) H6 0.063(13) 0.156(17) 0.31(3) -0.006(12) 0.025(16) 0.023(18) H12 0.062(10) 0.077(7) 0.099(9) -0.014(6) 0.018(8) 0.008(6) O2 0.054(5) 0.058(4) 0.122(6) 0.004(3) 0.035(4) 0.005(4) O1 0.075(6) 0.057(4) 0.144(7) 0.017(4) 0.024(5) -0.015(4) F1 0.081(7) 0.070(5) 0.169(10) -0.007(4) 0.046(6) 0.015(5) C11 0.057(4) 0.049(3) 0.070(3) -0.003(2) 0.017(3) 0.005(2) C9 0.058(4) 0.056(3) 0.070(4) 0.011(3) 0.006(3) 0.003(2) H9 0.101(11) 0.075(8) 0.146(14) 0.036(8) 0.038(9) 0.010(8) N1 0.051(3) 0.064(2) 0.072(3) -0.0016(18) 0.015(2) 0.0045(19) O3 0.072(6) 0.053(4) 0.124(7) 0.001(4) 0.041(5) 0.013(4) C10 0.058(5) 0.065(3) 0.074(4) 0.001(3) 0.017(3) 0.004(3) C6 0.051(4) 0.047(3) 0.066(3) 0.006(3) 0.006(3) -0.004(2) C4 0.048(4) 0.035(3) 0.069(3) -0.003(2) 0.013(3) 0.001(2) C5 0.048(4) 0.047(3) 0.075(4) 0.003(2) 0.022(3) 0.007(2) C13 0.046(3) 0.042(2) 0.048(3) -0.0023(19) 0.008(2) -0.0022(19) C7 0.054(6) 0.082(5) 0.080(5) 0.010(4) 0.016(4) 0.003(4) C3 0.046(4) 0.043(2) 0.055(3) 0.002(2) 0.003(2) -0.005(2) C12 0.046(4) 0.042(3) 0.070(3) 0.001(2) 0.012(3) 0.000(2) C8 0.055(4) 0.044(3) 0.066(3) 0.004(2) 0.013(3) 0.002(2) C2 0.058(4) 0.034(3) 0.082(4) 0.001(2) 0.006(3) 0.006(2) C14 0.050(3) 0.048(3) 0.057(3) -0.003(2) 0.010(2) -0.007(2) C1 0.063(5) 0.047(3) 0.076(4) -0.011(3) 0.009(3) 0.006(2) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O2 C14 . 1.222(8) ? O1 C6 . 1.215(8) ? F1 C11 . 1.345(10) ? C11 C12 . 1.389(8) ? C11 C10 . 1.393(8) ? C9 C10 . 1.383(9) ? C9 C8 . 1.395(8) ? N1 C1 . 1.330(7) ? N1 C5 . 1.332(7) ? O3 C14 . 1.324(9) ? C6 C7 . 1.499(10) ? C6 C3 . 1.500(8) ? C4 C5 . 1.381(8) ? C4 C3 . 1.392(6) ? C13 C12 . 1.383(7) ? C13 C8 . 1.391(7) ? C13 C14 . 1.493(8) ? C3 C2 . 1.394(8) ? C2 C1 . 1.386(9) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F1 C11 C12 118.5(6) . . ? F1 C11 C10 118.9(7) . . ? C12 C11 C10 122.6(5) . . ? C10 C9 C8 121.0(6) . . ? C1 N1 C5 118.5(5) . . ? C9 C10 C11 117.9(7) . . ? O1 C6 C7 121.9(7) . . ? O1 C6 C3 119.4(6) . . ? C7 C6 C3 118.7(5) . . ? C5 C4 C3 118.9(5) . . ? N1 C5 C4 122.7(5) . . ? C12 C13 C8 120.8(6) . . ? C12 C13 C14 118.3(5) . . ? C8 C13 C14 120.9(5) . . ? C4 C3 C2 118.4(6) . . ? C4 C3 C6 122.5(5) . . ? C2 C3 C6 119.1(4) . . ? C13 C12 C11 118.2(5) . . ? C13 C8 C9 119.6(6) . . ? C1 C2 C3 118.3(5) . . ? O2 C14 O3 123.7(7) . . ? O2 C14 C13 122.1(6) . . ? O3 C14 C13 114.2(6) . . ? N1 C1 C2 123.0(5) . . ? 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_site_symmetry_A O3 H12 N1 1.04(2) 1.615(18) 2.657(11) 175.8(11) . # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF # Attachment '- neutron_formII.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2010-02-10 at 13:01:44 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.4 # Request file : c:\wingx old2\files\acta.reqdat # CIF files read : fpay150s #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_neutron_formII _database_code_depnum_ccdc_archive 'CCDC 810550' #TrackingRef '- neutron_formII.cif' #------------------ AUDIT DETAILS -------------------------------------------# #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; 3-fluorobenzoic acid 4-acetylpyridine ; _chemical_formula_sum 'C14 H12 F N O3' _chemical_formula_weight 261.25 #============================================================================== # CRYSTAL DATA _symmetry_space_group_name_H-M P21/n _symmetry_cell_setting monoclinic 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' _cell_length_a 7.9892(15) _cell_length_b 6.9703(14) _cell_length_c 21.947(4) _cell_angle_alpha 90 _cell_angle_beta 95.670(12) _cell_angle_gamma 90 _cell_volume 1216.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _exptl_crystal_size_max 6 _exptl_crystal_size_mid 3 _exptl_crystal_size_min 1 _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 322 _exptl_absorpt_coefficient_mu 0.136 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details 'SXD2001 (Gutmann, 2001)' #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; For peak integration a local UB matrix refined for each frame, using approximately 100 reflections from each of the 11 detectors. Hence _cell_measurement_reflns_used 1000 For final cell dimensions a weighted average of all local cells from each frame was calculated. 5 frames of data were collected Because of the nature of the experiment, it is not possible to give values of theta_min and theta_max for the cell determination. The same applies for the wavelength used for the experiment. The range of wavelengths used was 0.7-6.9 Angstroms, BUT the bulk of the diffraction information is obtained from wavelengths in the range 0.8-2.9 Angstroms. The data collection procedures on the SXD instrument used for the single crystal neutron data collection are most recently summarised the following paper D. A. Keen, M. J. Gutmann and C. C. Wilson, J. Appl. Cryst., 2006, 39, 714. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.7-6.9 _diffrn_radiation_probe neutron _diffrn_radiation_type neutron _diffrn_radiation_source 'ISIS spallation source' _diffrn_measurement_device_type 'SXD time-of-flight LAUE diffraction' _diffrn_measurement_method 'time-of-flight LAUE diffraction' _diffrn_reflns_number 7921 _diffrn_reflns_av_unetI/netI 0.1051 _diffrn_reflns_theta_min 10.26 _diffrn_reflns_theta_max 83.3 _diffrn_reflns_theta_full 83.3 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 42 #============================================================================== # STRUCTURE SOLUTION _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap #============================================================================== # REFINEMENT DATA _refine_special_details ; The variable wavelength nature of the data collection procedure means that sensible values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max cannot be given instead the following limits are given _diffrn_reflns_sin(theta)/lambda_min 0.09 _diffrn_reflns_sin(theta)/lambda_max 1.30 _refine_diff_density_max/min is given in Fermi per per angstrom cubed not electons per angstrom cubed. Another way to consider the _refine_diff_density_ is as a percentage of the diffracted intensity of a given atom: _refine_diff_density_max = 7.49% of Carbon _refine_diff_density_min = -4.32% of Carbon Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 7921 _reflns_number_gt 7921 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0962 _refine_ls_R_factor_gt 0.0962 _refine_ls_wR_factor_ref 0.2423 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _refine_ls_number_reflns 7921 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment refall _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.654 _refine_diff_density_min -1.442 _refine_diff_density_rms 0.339 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00471(18) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'SXD2001 (Gutmann, 2001)' _computing_cell_refinement 'SXD2001 (Gutmann, 2001)' _computing_data_reduction 'SXD2001 (Gutmann, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 1.2457(4) -0.5392(5) 0.17327(15) 0.0280(8) Uani d . 1 . . O N1 0.9394(2) 0.0845(3) 0.14910(9) 0.0206(4) Uani d . 1 . . N C1 1.0317(3) 0.0015(4) 0.19582(12) 0.0194(5) Uani d . 1 . . C C2 1.1063(3) -0.1778(4) 0.19098(11) 0.0175(5) Uani d . 1 . . C C3 1.0863(2) -0.2733(4) 0.13471(11) 0.0148(5) Uani d . 1 . . C C4 0.9914(3) -0.1849(4) 0.08615(12) 0.0181(5) Uani d . 1 . . C C5 0.9199(3) -0.0062(4) 0.09536(12) 0.0196(5) Uani d . 1 . . C C6 1.1684(3) -0.4658(4) 0.12893(11) 0.0171(5) Uani d . 1 . . C C7 1.1495(3) -0.5634(5) 0.06788(13) 0.0249(6) Uani d . 1 . . C H1 1.0471(7) 0.0787(10) 0.2390(3) 0.0428(16) Uani d . 1 . . H H2 1.1794(7) -0.2405(9) 0.2301(3) 0.0369(14) Uani d . 1 . . H H3 0.9703(8) -0.2520(10) 0.0410(3) 0.0425(15) Uani d . 1 . . H H4 0.8394(7) 0.0663(10) 0.0588(3) 0.0425(16) Uani d . 1 . . H H5 1.1982(8) -0.4754(12) 0.0328(3) 0.0493(18) Uani d . 1 . . H H6 1.0170(7) -0.5885(11) 0.0543(3) 0.0463(17) Uani d . 1 . . H H7 1.2163(10) -0.6981(11) 0.0698(3) 0.058(2) Uani d . 1 . . H O2 0.6932(4) 0.3980(6) 0.06542(15) 0.0293(8) Uani d . 1 . . O O3 0.7801(4) 0.4090(5) 0.16485(15) 0.0250(7) Uani d . 1 . . O F1 0.3473(4) 1.0067(6) 0.03624(16) 0.0312(8) Uani d . 1 . . F C8 0.6317(3) 0.7587(4) 0.18115(11) 0.0176(5) Uani d . 1 . . C C9 0.5551(3) 0.9363(4) 0.18811(13) 0.0208(6) Uani d . 1 . . C C10 0.4603(3) 1.0215(4) 0.13917(12) 0.0209(6) Uani d . 1 . . C C11 0.4426(3) 0.9255(4) 0.08338(12) 0.0203(6) Uani d . 1 . . C C12 0.5160(3) 0.7488(4) 0.07454(12) 0.0177(5) Uani d . 1 . . C C13 0.6127(3) 0.6651(4) 0.12451(11) 0.0154(5) Uani d . 1 . . C C14 0.6979(3) 0.4787(4) 0.11517(12) 0.0180(5) Uani d . 1 . . C H8 0.7076(6) 0.6953(9) 0.2192(2) 0.0324(13) Uani d . 1 . . H H9 0.5714(7) 1.0056(10) 0.2324(3) 0.0427(15) Uani d . 1 . . H H10 0.3987(7) 1.1606(10) 0.1438(3) 0.0397(15) Uani d . 1 . . H H11 0.5010(7) 0.6797(10) 0.0304(3) 0.0378(14) Uani d . 1 . . H H12 0.8421(6) 0.2784(9) 0.1560(3) 0.0329(13) Uani d . 1 . . H 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 O1 0.0384(15) 0.023(2) 0.0207(16) 0.0135(13) -0.0092(12) -0.0009(14) N1 0.0223(7) 0.0161(11) 0.0227(10) 0.0029(7) -0.0003(6) -0.0024(9) C1 0.0217(9) 0.0188(15) 0.0171(12) 0.0030(10) -0.0017(8) -0.0032(11) C2 0.0185(9) 0.0196(15) 0.0141(12) 0.0029(9) -0.0003(8) 0.0001(11) C3 0.0148(8) 0.0157(15) 0.0134(11) -0.0007(8) -0.0008(8) -0.0018(10) C4 0.0212(9) 0.0187(16) 0.0136(12) 0.0032(9) -0.0028(8) -0.0009(11) C5 0.0242(10) 0.0157(15) 0.0176(12) 0.0028(9) -0.0039(9) 0.0014(11) C6 0.0199(9) 0.0162(16) 0.0145(12) 0.0029(9) -0.0022(8) -0.0007(10) C7 0.0329(13) 0.0244(19) 0.0166(13) 0.0062(11) -0.0017(10) -0.0050(12) H1 0.053(3) 0.044(4) 0.029(3) 0.008(3) -0.007(2) -0.020(3) H2 0.045(3) 0.040(4) 0.023(3) 0.011(3) -0.010(2) -0.001(3) H3 0.058(3) 0.040(5) 0.026(3) 0.008(3) -0.009(2) -0.006(3) H4 0.054(3) 0.039(4) 0.031(3) 0.011(3) -0.017(2) 0.008(3) H5 0.060(3) 0.062(6) 0.028(3) -0.001(3) 0.018(3) -0.002(3) H6 0.045(3) 0.054(5) 0.039(4) -0.001(3) -0.001(3) -0.013(3) H7 0.086(5) 0.041(5) 0.043(4) 0.037(4) -0.012(3) -0.015(4) O2 0.0414(15) 0.028(2) 0.0172(15) 0.0107(14) -0.0016(12) -0.0050(14) O3 0.0339(14) 0.0205(19) 0.0192(15) 0.0109(13) -0.0041(11) 0.0017(14) F1 0.0306(13) 0.038(2) 0.0241(17) 0.0163(15) -0.0018(12) 0.0057(17) C8 0.0189(9) 0.0208(16) 0.0130(11) 0.0017(9) 0.0002(8) -0.0005(10) C9 0.0220(10) 0.0206(16) 0.0196(13) 0.0028(10) 0.0014(9) -0.0020(12) C10 0.0200(10) 0.0201(17) 0.0222(14) 0.0062(10) 0.0009(9) 0.0015(12) C11 0.0185(9) 0.0239(16) 0.0182(12) 0.0059(10) 0.0003(8) 0.0036(11) C12 0.0174(9) 0.0184(16) 0.0174(12) 0.0033(9) 0.0020(9) 0.0014(11) C13 0.0159(8) 0.0142(14) 0.0159(12) 0.0002(9) 0.0013(8) 0.0031(10) C14 0.0213(9) 0.0161(16) 0.0165(12) -0.0002(9) 0.0015(8) 0.0018(11) H8 0.036(2) 0.035(4) 0.024(3) 0.010(2) -0.008(2) 0.004(2) H9 0.054(3) 0.044(4) 0.028(3) 0.013(3) -0.008(2) -0.018(3) H10 0.049(3) 0.028(4) 0.041(4) 0.018(3) -0.001(3) 0.000(3) H11 0.046(3) 0.041(4) 0.025(3) 0.005(3) -0.006(2) -0.006(3) H12 0.041(3) 0.025(4) 0.032(3) 0.005(2) -0.002(2) -0.003(2) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C6 . 1.213(4) ? N1 C5 . 1.334(3) ? N1 C1 . 1.334(3) ? C1 C2 . 1.393(4) ? C2 C3 . 1.398(3) ? C3 C4 . 1.389(3) ? C3 C6 . 1.504(4) ? C4 C5 . 1.393(4) ? C6 C7 . 1.497(4) ? O2 C14 . 1.226(4) ? O3 C14 . 1.310(4) ? F1 C11 . 1.347(4) ? C8 C9 . 1.396(4) ? C8 C13 . 1.399(4) ? C9 C10 . 1.386(4) ? C10 C11 . 1.390(4) ? C11 C12 . 1.386(4) ? C12 C13 . 1.405(3) ? C13 C14 . 1.490(4) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C1 118.8(2) . . ? N1 C1 C2 122.6(2) . . ? C1 C2 C3 118.8(2) . . ? C4 C3 C2 118.2(2) . . ? C4 C3 C6 122.7(2) . . ? C2 C3 C6 119.1(2) . . ? C3 C4 C5 119.0(2) . . ? N1 C5 C4 122.6(2) . . ? O1 C6 C7 121.6(3) . . ? O1 C6 C3 120.0(3) . . ? C7 C6 C3 118.3(2) . . ? C9 C8 C13 120.0(2) . . ? C10 C9 C8 120.5(2) . . ? C9 C10 C11 118.4(3) . . ? F1 C11 C12 118.7(3) . . ? F1 C11 C10 118.3(3) . . ? C12 C11 C10 122.9(2) . . ? C11 C12 C13 117.9(2) . . ? C8 C13 C12 120.2(2) . . ? C8 C13 C14 121.2(2) . . ? C12 C13 C14 118.6(2) . . ? O2 C14 O3 122.7(3) . . ? O2 C14 C13 123.3(3) . . ? O3 C14 C13 114.0(3) . . ? 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_site_symmetry_A O3 H12 N1 1.064(7) 1.574(6) 2.635(4) 174.9(5) . # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF