#------------------------------------------------------------------------------ #$Date: 2017-10-13 07:09:21 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201973 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/51/2205101.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_2205101 loop_ _publ_author_name 'Yathirajan, H. S.' 'Narasimhamurthy, T.' 'Nagaraj, B.' 'Nagaraja, P.' 'Narasegowda, R. S.' 'Rathore, Ravindranath S.' _publ_section_title ; N---H^+^···Cl^{-^} and C---H···O interactions in 6-fluoro-3-(4-piperidinio)benz[d]isoxazole chloride ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o356 _journal_page_last o358 _journal_paper_doi 10.1107/S1600536805000899 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C12 H14 F N2 O +, Cl -' _chemical_formula_moiety 'C12 H14 F N2 O +, Cl -' _chemical_formula_sum 'C12 H14 Cl F N2 O' _chemical_formula_weight 256.70 _chemical_name_systematic ; 6-fluoro-3-(4-piperidinio)benz[d]isoxazole chloride ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 113.109(7) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 13.020(6) _cell_length_b 6.608(3) _cell_length_c 15.119(7) _cell_measurement_reflns_used 998 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 55 _cell_measurement_theta_min 7 _cell_volume 1196.4(10) _computing_cell_refinement 'SAINT-Plus (Bruker, 2001)' _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction SAINT-Plus _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and PLUTON (Spek, 1999)' _computing_publication_material 'WinGX (Farrugia, 1999) and PARST (Nardelli, 1995)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 566(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0148 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 13392 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.98 _diffrn_reflns_theta_min 1.70 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.317 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_correction_T_min 0.971 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.425 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Needle _exptl_crystal_F_000 536 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.260 _refine_diff_density_min -0.317 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 210 _refine_ls_number_reflns 2854 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.096 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0422 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.068P)^2^+0.2204P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1116 _refine_ls_wR_factor_ref 0.1155 _reflns_number_gt 2554 _reflns_number_total 2854 _reflns_threshold_expression I>2\s(I) _cod_data_source_file kp6027.cif _cod_data_source_block I _cod_original_cell_volume 1196.4(9) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2205101 _cod_database_fobs_code 2205101 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_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_occupancy _atom_site_type_symbol Cl1 0.90572(3) 0.80225(6) 0.81904(3) 0.04445(14) Uani d 1 Cl F1 0.19378(8) 0.68630(18) 0.17792(10) 0.0722(4) Uani d 1 F O1 0.51737(9) 0.37273(16) 0.40873(8) 0.0458(3) Uani d 1 O N1 0.62713(10) 0.45145(18) 0.46085(9) 0.0420(3) Uani d 1 N N2 0.91903(11) 0.9547(2) 0.62951(9) 0.0431(3) Uani d 1 N H2A 0.9155(18) 0.904(4) 0.6879(17) 0.071(6) Uiso d 1 H H2B 0.983(2) 1.043(4) 0.6486(17) 0.074(7) Uiso d 1 H C1 0.45417(12) 0.5255(2) 0.35510(10) 0.0365(3) Uani d 1 C C2 0.51628(11) 0.7022(2) 0.37091(10) 0.0327(3) Uani d 1 C C3 0.62493(11) 0.6419(2) 0.43840(10) 0.0334(3) Uani d 1 C C4 0.72809(11) 0.7697(2) 0.47804(10) 0.0339(3) Uani d 1 C H4 0.7355(15) 0.829(2) 0.4222(12) 0.039(4) Uiso d 1 H C5 0.71414(13) 0.9426(2) 0.54063(12) 0.0422(3) Uani d 1 C H5A 0.7055(16) 0.886(3) 0.5957(14) 0.051(5) Uiso d 1 H H5B 0.6486(17) 1.022(3) 0.5055(15) 0.055(5) Uiso d 1 H C6 0.81693(14) 1.0762(2) 0.57675(13) 0.0472(4) Uani d 1 C H6A 0.8106(18) 1.177(3) 0.6212(16) 0.065(6) Uiso d 1 H H6B 0.8283(18) 1.134(3) 0.5254(16) 0.062(6) Uiso d 1 H C7 0.93497(13) 0.7844(3) 0.57111(13) 0.0470(4) Uani d 1 C H7A 1.0038(19) 0.710(3) 0.6136(16) 0.067(6) Uiso d 1 H H7B 0.9503(16) 0.845(3) 0.5148(14) 0.052(5) Uiso d 1 H C8 0.83286(12) 0.6491(2) 0.53548(12) 0.0406(3) Uani d 1 C H8A 0.8232(14) 0.580(3) 0.5899(13) 0.049(5) Uiso d 1 H H8B 0.8450(16) 0.551(3) 0.4961(15) 0.057(5) Uiso d 1 H C9 0.46733(12) 0.8796(2) 0.32252(11) 0.0379(3) Uani d 1 C H9 0.5063(14) 1.001(3) 0.3321(12) 0.042(4) Uiso d 1 H C10 0.35717(13) 0.8715(3) 0.25845(12) 0.0447(4) Uani d 1 C H10 0.3207(16) 0.987(3) 0.2229(14) 0.056(5) Uiso d 1 H C11 0.30041(12) 0.6883(3) 0.24399(12) 0.0457(4) Uani d 1 C C12 0.34323(13) 0.5108(3) 0.29069(12) 0.0439(3) Uani d 1 C H12 0.3020(16) 0.400(3) 0.2766(13) 0.051(5) 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 Cl1 0.0414(2) 0.0431(2) 0.0450(2) 0.00619(14) 0.01274(16) 0.00682(14) F1 0.0307(5) 0.0748(8) 0.0844(8) 0.0021(5) -0.0064(5) 0.0028(6) O1 0.0383(6) 0.0342(5) 0.0538(6) -0.0058(4) 0.0063(5) 0.0036(5) N1 0.0338(6) 0.0351(6) 0.0473(7) -0.0031(5) 0.0054(5) 0.0024(5) N2 0.0392(7) 0.0433(7) 0.0377(6) -0.0123(5) 0.0053(5) 0.0000(5) C1 0.0331(7) 0.0354(7) 0.0385(7) -0.0026(5) 0.0113(6) 0.0000(5) C2 0.0303(6) 0.0333(7) 0.0331(6) -0.0014(5) 0.0107(5) -0.0014(5) C3 0.0311(6) 0.0326(6) 0.0334(6) -0.0012(5) 0.0095(5) -0.0009(5) C4 0.0307(6) 0.0333(6) 0.0332(6) -0.0024(5) 0.0076(5) 0.0015(5) C5 0.0364(8) 0.0353(7) 0.0491(8) -0.0003(6) 0.0104(6) -0.0050(6) C6 0.0494(9) 0.0346(7) 0.0492(9) -0.0067(7) 0.0102(7) -0.0039(7) C7 0.0313(7) 0.0483(9) 0.0539(10) -0.0047(6) 0.0086(7) -0.0031(7) C8 0.0297(7) 0.0366(7) 0.0486(8) -0.0012(5) 0.0079(6) -0.0030(6) C9 0.0352(7) 0.0345(7) 0.0417(7) 0.0006(6) 0.0128(6) 0.0024(6) C10 0.0380(8) 0.0443(8) 0.0461(8) 0.0080(6) 0.0105(6) 0.0060(7) C11 0.0267(7) 0.0568(9) 0.0462(8) 0.0020(6) 0.0064(6) -0.0031(7) C12 0.0319(7) 0.0444(8) 0.0514(9) -0.0081(6) 0.0119(6) -0.0047(7) 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' Cl Cl 0.1484 0.1585 '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 C1 O1 N1 107.44(11) C3 N1 O1 107.03(11) C6 N2 C7 113.05(12) C6 N2 H2A 108.9(14) C7 N2 H2A 110.5(14) C6 N2 H2B 108.4(14) C7 N2 H2B 109.4(14) H2A N2 H2B 106.4(19) O1 C1 C2 110.41(12) O1 C1 C12 125.93(13) C2 C1 C12 123.64(14) C1 C2 C9 120.08(13) C1 C2 C3 103.50(12) C9 C2 C3 136.40(13) N1 C3 C2 111.60(12) N1 C3 C4 121.11(13) C2 C3 C4 127.24(12) C3 C4 C8 113.24(12) C3 C4 C5 111.15(12) C8 C4 C5 109.47(12) C3 C4 H4 105.1(11) C8 C4 H4 109.6(10) C5 C4 H4 108.1(10) C6 C5 C4 110.70(13) C6 C5 H5A 107.6(12) C4 C5 H5A 109.1(12) C6 C5 H5B 110.4(12) C4 C5 H5B 110.9(12) H5A C5 H5B 108.1(16) N2 C6 C5 110.82(13) N2 C6 H6A 107.4(13) C5 C6 H6A 110.2(13) N2 C6 H6B 105.6(14) C5 C6 H6B 110.3(14) H6A C6 H6B 112.4(19) N2 C7 C8 110.39(14) N2 C7 H7A 106.7(13) C8 C7 H7A 112.2(13) N2 C7 H7B 108.1(11) C8 C7 H7B 111.4(11) H7A C7 H7B 107.9(16) C7 C8 C4 111.01(13) C7 C8 H8A 110.9(11) C4 C8 H8A 109.7(10) C7 C8 H8B 107.0(12) C4 C8 H8B 109.7(12) H8A C8 H8B 108.5(17) C10 C9 C2 118.04(14) C10 C9 H9 119.7(11) C2 C9 H9 122.3(11) C9 C10 C11 119.04(14) C9 C10 H10 121.2(12) C11 C10 H10 119.7(12) F1 C11 C12 117.60(15) F1 C11 C10 116.88(15) C12 C11 C10 125.52(14) C11 C12 C1 113.64(14) C11 C12 H12 119.9(13) C1 C12 H12 126.4(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F1 C11 1.3553(18) O1 C1 1.3529(18) O1 N1 1.4317(17) N1 C3 1.3007(19) N2 C6 1.489(2) N2 C7 1.494(2) N2 H2A 0.96(2) N2 H2B 0.96(3) C1 C2 1.387(2) C1 C12 1.393(2) C2 C9 1.396(2) C2 C3 1.4382(19) C3 C4 1.4984(19) C4 C8 1.523(2) C4 C5 1.539(2) C4 H4 0.970(17) C5 C6 1.515(2) C5 H5A 0.96(2) C5 H5B 0.96(2) C6 H6A 0.97(2) C6 H6B 0.93(2) C7 C8 1.515(2) C7 H7A 1.00(2) C7 H7B 1.03(2) C8 H8A 0.991(19) C8 H8B 0.93(2) C9 C10 1.381(2) C9 H9 0.930(18) C10 C11 1.390(2) C10 H10 0.95(2) C11 C12 1.370(2) C12 H12 0.88(2) 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 N2 H2A Cl1 . 0.96(3) 2.15(3) 3.106(2) 178 y N2 H2B Cl1 2_756 0.96(3) 2.17(2) 3.113(2) 166 y C7 H7A F1 4_676 1.00(2) 2.38(2) 3.119(2) 130 y C9 H9 O1 1_565 0.93(2) 2.69(2) 3.475(2) 142 y 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 C1 O1 N1 C3 0.97(16) N1 O1 C1 C2 -1.29(16) N1 O1 C1 C12 177.14(15) O1 C1 C2 C9 179.87(13) C12 C1 C2 C9 1.4(2) O1 C1 C2 C3 1.08(16) C12 C1 C2 C3 -177.39(14) O1 N1 C3 C2 -0.30(16) O1 N1 C3 C4 -177.88(12) C1 C2 C3 N1 -0.46(16) C9 C2 C3 N1 -178.94(16) C1 C2 C3 C4 176.95(13) C9 C2 C3 C4 -1.5(3) N1 C3 C4 C8 6.3(2) C2 C3 C4 C8 -170.84(13) N1 C3 C4 C5 -117.37(15) C2 C3 C4 C5 65.45(18) C3 C4 C5 C6 -177.53(13) C8 C4 C5 C6 56.63(17) C7 N2 C6 C5 55.83(19) C4 C5 C6 N2 -55.70(18) C6 N2 C7 C8 -55.94(19) N2 C7 C8 C4 56.50(19) C3 C4 C8 C7 178.20(13) C5 C4 C8 C7 -57.17(18) C1 C2 C9 C10 -0.9(2) C3 C2 C9 C10 177.38(15) C2 C9 C10 C11 -0.8(2) C9 C10 C11 F1 -177.70(14) C9 C10 C11 C12 2.2(3) F1 C11 C12 C1 178.19(14) C10 C11 C12 C1 -1.7(3) O1 C1 C12 C11 -178.34(15) C2 C1 C12 C11 -0.1(2) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 9509305