#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2013901.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_2013901 loop_ _publ_author_name 'K\"oysal, Yavuz' 'I\,s\?ik, \,Samil' 'K\"oksal, Meri\,c' 'Erd\~ogan, Hakk\?i' 'Gokhan, Nesrin' _publ_section_title ; 3-[4-(4-Fluorophenyl)piperazin-1-ylmethyl]-5-methyl-1,3-benzoxazol-2(3H)-one and 3-[4-(2-fluorophenyl)piperazin-1-ylmethyl]-5-methyl-1,3-benzoxazol-2(3H)-one ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o232 _journal_page_last o234 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C19 H20 F N3 O2' _chemical_formula_moiety 'C19 H20 F N3 O2' _chemical_formula_sum 'C19 H20 F N3 O2' _chemical_formula_weight 341.22 _chemical_name_systematic ; 3-[4-(4-Fluorophenyl)piperazin-1-ylmethyl]-5-methyl-1,3-benzoxazol-2(3H)-one ; _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 constr _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 103.067(7) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.1788(6) _cell_length_b 6.1512(4) _cell_length_c 34.090(3) _cell_measurement_reflns_used 10038 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.42 _cell_measurement_theta_min 0.00 _cell_volume 1670.6(2) _computing_cell_refinement 'STOE X-AREA' _computing_data_collection 'STOE X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'STOE X-RED (Stoe & Cie, 2002)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material 'WinGX (Farrugia, 1997) and PARST (Nardelli, 1995)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method '\w scan' _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 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_number 7820 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_min 2.56 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_T_max 0.9688 _exptl_absorpt_correction_T_min 0.9397 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details '(STOE X-RED; Stoe & Cie, 2002)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 720 _exptl_crystal_size_max 0.620 _exptl_crystal_size_mid 0.480 _exptl_crystal_size_min 0.350 _refine_diff_density_max 0.945 _refine_diff_density_min -0.426 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_hydrogen_treatment 'see text' _refine_ls_matrix_type full _refine_ls_number_parameters 240 _refine_ls_number_reflns 3072 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.067 _refine_ls_R_factor_all 0.0954 _refine_ls_R_factor_gt 0.0796 _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^)+(0.1428P)^2^+0.916P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2331 _refine_ls_wR_factor_ref 0.2504 _reflns_number_gt 2368 _reflns_number_total 3072 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file av1163.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2013901 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_refinement_flags _atom_site_occupancy _atom_site_type_symbol F1 -0.4451(3) 0.1980(4) 0.25278(8) 0.0883(8) Uani d . 1 F O1 0.6376(4) 0.7349(5) 0.11743(9) 0.0921(9) Uani d . 1 O O2 0.5004(3) 0.8047(3) 0.05353(7) 0.0634(6) Uani d . 1 O N1 0.0705(3) 0.2670(4) 0.17372(9) 0.0623(7) Uani d . 1 N N2 0.3002(4) 0.3067(4) 0.12303(9) 0.0709(9) Uani d . 1 N N3 0.4476(3) 0.4915(4) 0.08023(7) 0.0523(6) Uani d . 1 N C1 -0.3220(4) 0.2157(6) 0.23245(11) 0.0624(8) Uani d . 1 C C2 -0.2266(4) 0.4004(6) 0.23707(11) 0.0661(9) Uani d . 1 C H2 -0.2467 0.5116 0.2538 0.076(11) Uiso d R 1 H C3 -0.0995(4) 0.4168(5) 0.21697(11) 0.0613(8) Uani d . 1 C H3 -0.0336 0.5416 0.2201 0.064(9) Uiso d R 1 H C4 -0.0671(3) 0.2523(4) 0.19178(9) 0.0512(7) Uani d . 1 C C5 -0.1692(4) 0.0694(5) 0.18714(10) 0.0584(8) Uani d . 1 C H5 -0.1527 -0.0418 0.1700 0.065(9) Uiso d R 1 H C6 -0.2963(4) 0.0526(6) 0.20758(11) 0.0661(9) Uani d . 1 C H6 -0.3639 -0.0705 0.2046 0.087(12) Uiso d R 1 H C7 0.1183(6) 0.4709(6) 0.16319(14) 0.0859(13) Uani d . 1 C H7A 0.1208 0.5700 0.1855 0.103 Uiso calc R 1 H H7B 0.0347 0.5239 0.1403 0.103 Uiso calc R 1 H C8 0.2901(5) 0.4735(5) 0.15245(11) 0.0641(9) Uani d . 1 C H8A 0.3007 0.6150 0.1408 0.077(11) Uiso d R 1 H H8B 0.3821 0.4572 0.1757 0.123(18) Uiso d R 1 H C9 0.2595(6) 0.1032(6) 0.13649(16) 0.0903(13) Uani d . 1 C H9A 0.3419 0.0649 0.1607 0.108 Uiso calc R 1 H H9B 0.2652 -0.0049 0.1161 0.108 Uiso calc R 1 H C10 0.0904(4) 0.0975(5) 0.14518(11) 0.0650(9) Uani d . 1 C H10A 0.0009 0.1073 0.1216 0.093(13) Uiso d R 1 H H10B 0.0827 -0.0417 0.1574 0.085(12) Uiso d R 1 H C11 0.4556(4) 0.3174(5) 0.10935(10) 0.0619(8) Uani d . 1 C H11A 0.4743 0.1801 0.0971 0.064(9) Uiso d R 1 H H11B 0.5490 0.3426 0.1321 0.083(12) Uiso d R 1 H C12 0.5398(4) 0.6778(5) 0.08766(11) 0.0621(8) Uani d . 1 C C13 0.3857(4) 0.6890(4) 0.02439(10) 0.0529(7) Uani d . 1 C C14 0.3172(4) 0.7473(5) -0.01371(11) 0.0634(8) Uani d . 1 C H14 0.3420 0.8795 -0.0242 0.073(10) Uiso d R 1 H C15 0.2082(4) 0.5990(6) -0.03666(11) 0.0641(8) Uani d . 1 C H15 0.1585 0.6333 -0.0633 0.068(10) Uiso d R 1 H C16 0.1698(4) 0.4003(5) -0.02106(10) 0.0556(7) Uani d . 1 C C17 0.2429(3) 0.3473(5) 0.01838(9) 0.0510(7) Uani d . 1 C H17 0.2191 0.2157 0.0293 0.054(8) Uiso d R 1 H C18 0.3520(3) 0.4937(4) 0.04108(9) 0.0473(6) Uani d . 1 C C19 0.0502(4) 0.2464(7) -0.04739(12) 0.0735(10) Uani d . 1 C H19A -0.0323 0.3280 -0.0662 0.110 Uiso calc R 1 H H19B -0.0047 0.1585 -0.0310 0.110 Uiso calc R 1 H H19C 0.1112 0.1545 -0.0618 0.110 Uiso calc R 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 F1 0.0737(13) 0.0909(16) 0.1090(19) 0.0017(11) 0.0390(13) 0.0125(13) O1 0.107(2) 0.0838(19) 0.0788(19) -0.0306(16) 0.0064(15) -0.0247(15) O2 0.0727(14) 0.0458(11) 0.0759(16) -0.0139(10) 0.0258(11) -0.0094(10) N1 0.0670(16) 0.0463(13) 0.0774(19) -0.0094(11) 0.0245(14) -0.0192(12) N2 0.107(2) 0.0521(15) 0.0659(18) -0.0184(15) 0.0459(17) -0.0141(12) N3 0.0636(14) 0.0477(12) 0.0476(13) -0.0058(10) 0.0170(11) -0.0057(10) C1 0.0516(15) 0.0680(19) 0.066(2) 0.0065(14) 0.0096(14) 0.0117(16) C2 0.0610(18) 0.0642(19) 0.074(2) 0.0031(15) 0.0172(16) -0.0077(17) C3 0.0609(17) 0.0521(16) 0.072(2) -0.0044(14) 0.0171(15) -0.0109(15) C4 0.0486(14) 0.0472(14) 0.0533(16) -0.0017(12) 0.0021(12) -0.0038(12) C5 0.0633(17) 0.0474(15) 0.0602(18) -0.0052(13) 0.0049(14) -0.0050(13) C6 0.0591(17) 0.0591(18) 0.076(2) -0.0087(15) 0.0069(16) 0.0037(16) C7 0.129(3) 0.0538(19) 0.094(3) -0.019(2) 0.066(3) -0.0174(18) C8 0.090(2) 0.0450(15) 0.063(2) -0.0118(15) 0.0309(18) -0.0095(14) C9 0.112(3) 0.055(2) 0.116(4) -0.007(2) 0.054(3) -0.020(2) C10 0.080(2) 0.0411(15) 0.078(2) -0.0082(14) 0.0261(18) -0.0144(15) C11 0.078(2) 0.0553(17) 0.0538(18) -0.0006(15) 0.0175(15) -0.0008(13) C12 0.0718(19) 0.0530(16) 0.065(2) -0.0096(14) 0.0229(16) -0.0128(14) C13 0.0553(15) 0.0426(14) 0.0669(19) -0.0001(12) 0.0268(14) -0.0011(13) C14 0.0672(18) 0.0512(16) 0.076(2) 0.0076(14) 0.0251(16) 0.0152(15) C15 0.0628(18) 0.0675(19) 0.0616(19) 0.0128(15) 0.0130(15) 0.0130(16) C16 0.0482(14) 0.0577(16) 0.0614(18) 0.0057(12) 0.0132(12) -0.0028(14) C17 0.0517(14) 0.0449(14) 0.0594(17) -0.0016(12) 0.0190(12) -0.0012(12) C18 0.0492(13) 0.0427(13) 0.0551(16) 0.0010(11) 0.0226(12) -0.0022(11) C19 0.0630(19) 0.078(2) 0.072(2) 0.0016(17) 0.0003(16) -0.0102(18) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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' F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 0.0060 '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 _geom_angle_publ_flag C12 O2 C13 107.7(2) ? C7 N1 C4 118.3(3) ? C7 N1 C10 113.2(3) ? C4 N1 C10 117.9(2) ? C9 N2 C8 110.6(3) ? C9 N2 C11 115.9(3) ? C8 N2 C11 112.4(3) ? C12 N3 C18 109.8(3) ? C12 N3 C11 123.7(3) ? C18 N3 C11 126.4(2) ? F1 C1 C6 119.9(3) ? F1 C1 C2 118.7(3) ? C6 C1 C2 121.3(3) ? C1 C2 C3 118.8(3) ? C1 C2 H2 120.5 ? C3 C2 H2 120.8 ? C2 C3 C4 121.8(3) ? C2 C3 H3 119.2 ? C4 C3 H3 119.1 ? C5 C4 C3 117.8(3) ? C5 C4 N1 121.6(3) ? C3 C4 N1 120.5(3) ? C6 C5 C4 120.3(3) ? C6 C5 H5 119.7 ? C4 C5 H5 119.9 ? C1 C6 C5 120.0(3) ? C1 C6 H6 119.9 ? C5 C6 H6 120.1 ? N1 C7 C8 113.6(3) yes N1 C7 H7A 108.9 ? C8 C7 H7A 108.9 ? N1 C7 H7B 108.9 ? C8 C7 H7B 108.9 ? H7A C7 H7B 107.7 ? N2 C8 C7 110.9(3) yes N2 C8 H8A 109.2 ? C7 C8 H8A 106.2 ? N2 C8 H8B 109.7 ? C7 C8 H8B 112.9 ? H8A C8 H8B 107.6 ? N2 C9 C10 113.0(3) yes N2 C9 H9A 109.0 ? C10 C9 H9A 109.0 ? N2 C9 H9B 109.0 ? C10 C9 H9B 109.0 ? H9A C9 H9B 107.8 ? N1 C10 C9 111.5(3) yes N1 C10 H10A 109.5 ? C9 C10 H10A 113.7 ? N1 C10 H10B 108.7 ? C9 C10 H10B 105.3 ? H10A C10 H10B 107.9 ? N2 C11 N3 110.2(3) yes N2 C11 H11A 109.6 ? N3 C11 H11A 109.5 ? N2 C11 H11B 109.9 ? N3 C11 H11B 109.5 ? H11A C11 H11B 108.1 ? O1 C12 N3 129.9(4) yes O1 C12 O2 122.4(3) yes N3 C12 O2 107.8(3) ? C14 C13 C18 123.5(3) ? C14 C13 O2 128.2(3) ? C18 C13 O2 108.3(3) ? C13 C14 C15 116.4(3) ? C13 C14 H14 121.9 ? C15 C14 H14 121.7 ? C14 C15 C16 122.1(3) ? C14 C15 H15 118.9 ? C16 C15 H15 118.9 ? C17 C16 C15 119.5(3) ? C17 C16 C19 120.8(3) ? C15 C16 C19 119.7(3) ? C18 C17 C16 118.4(3) ? C18 C17 H17 120.8 ? C16 C17 H17 120.8 ? C17 C18 C13 120.1(3) ? C17 C18 N3 133.5(3) ? C13 C18 N3 106.4(3) ? C16 C19 H19A 109.5 ? C16 C19 H19B 109.5 ? H19A C19 H19B 109.5 ? C16 C19 H19C 109.5 ? H19A C19 H19C 109.5 ? H19B C19 H19C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag F1 C1 1.350(4) yes O1 C12 1.194(4) yes O2 C12 1.377(4) yes O2 C13 1.397(4) yes N1 C7 1.385(4) yes N1 C4 1.402(4) yes N1 C10 1.460(4) yes N2 C9 1.399(5) yes N2 C8 1.450(4) yes N2 C11 1.451(4) yes N3 C12 1.364(4) yes N3 C18 1.386(4) yes N3 C11 1.452(4) yes C1 C6 1.360(5) ? C1 C2 1.366(5) ? C2 C3 1.372(5) ? C2 H2 0.9298 ? C3 C4 1.391(4) ? C3 H3 0.9299 ? C4 C5 1.389(4) ? C5 C6 1.380(5) ? C5 H5 0.9296 ? C6 H6 0.9300 ? C7 C8 1.530(5) ? C7 H7A 0.9700 ? C7 H7B 0.9700 ? C8 H8A 0.9680 ? C8 H8B 0.9661 ? C9 C10 1.479(5) ? C9 H9A 0.9700 ? C9 H9B 0.9700 ? C10 H10A 0.9588 ? C10 H10B 0.9594 ? C11 H11A 0.9701 ? C11 H11B 0.9697 ? C13 C14 1.342(5) ? C13 C18 1.384(4) ? C14 C15 1.387(5) ? C14 H14 0.9298 ? C15 C16 1.396(5) ? C15 H15 0.9301 ? C16 C17 1.381(4) ? C16 C19 1.504(5) ? C17 C18 1.376(4) ? C17 H17 0.9299 ? C19 H19A 0.9600 ? C19 H19B 0.9600 ? C19 H19C 0.9600 ? 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 C5 H5 O1 1_445 0.93 2.58 3.268(4) 131 C14 H14 O2 3_675 0.93 2.65 3.547(4) 163 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_publ_flag F1 C1 C2 C3 178.9(3) ? C6 C1 C2 C3 -2.0(5) ? C1 C2 C3 C4 0.9(5) ? C2 C3 C4 C5 0.6(5) ? C2 C3 C4 N1 -175.7(3) ? C7 N1 C4 C5 150.7(4) yes C10 N1 C4 C5 8.4(5) yes C7 N1 C4 C3 -33.2(5) ? C10 N1 C4 C3 -175.4(3) ? C3 C4 C5 C6 -1.0(5) ? N1 C4 C5 C6 175.3(3) ? F1 C1 C6 C5 -179.2(3) ? C2 C1 C6 C5 1.6(5) ? C4 C5 C6 C1 -0.1(5) ? C4 N1 C7 C8 167.4(3) ? C10 N1 C7 C8 -48.7(5) ? C9 N2 C8 C7 -54.1(5) ? C11 N2 C8 C7 174.7(3) ? N1 C7 C8 N2 50.8(5) yes C8 N2 C9 C10 57.7(5) ? C11 N2 C9 C10 -172.9(3) ? C7 N1 C10 C9 50.0(5) ? C4 N1 C10 C9 -165.9(3) ? N2 C9 C10 N1 -54.9(5) yes C9 N2 C11 N3 153.6(3) ? C8 N2 C11 N3 -77.9(4) ? C12 N3 C11 N2 110.5(3) ? C18 N3 C11 N2 -71.4(4) ? C18 N3 C12 O1 -179.2(3) ? C11 N3 C12 O1 -0.9(5) ? C18 N3 C12 O2 1.7(3) ? C11 N3 C12 O2 180.0(2) ? C13 O2 C12 O1 178.9(3) ? C13 O2 C12 N3 -1.9(3) ? C12 O2 C13 C14 -177.9(3) ? C12 O2 C13 C18 1.5(3) ? C18 C13 C14 C15 -0.4(4) ? O2 C13 C14 C15 178.9(3) ? C13 C14 C15 C16 0.7(5) ? C14 C15 C16 C17 -0.5(5) ? C14 C15 C16 C19 179.8(3) ? C15 C16 C17 C18 0.0(4) ? C19 C16 C17 C18 179.7(3) ? C16 C17 C18 C13 0.3(4) ? C16 C17 C18 N3 -178.4(3) ? C14 C13 C18 C17 -0.1(4) ? O2 C13 C18 C17 -179.5(2) ? C14 C13 C18 N3 178.9(3) ? O2 C13 C18 N3 -0.4(3) ? C12 N3 C18 C17 178.1(3) ? C11 N3 C18 C17 -0.1(5) ? C12 N3 C18 C13 -0.8(3) ? C11 N3 C18 C13 -179.0(3) ?