#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/21/05/2210529.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_2210529 loop_ _publ_author_name 'Wang, Chen-Yi' 'Guo, Ling-Xiang' 'Chen, Jian-Zhong' 'Xia, Ping' _publ_section_title ; 1-(2,4-Difluorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-1-one ; _journal_coeditor_code BX2021 _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o4331 _journal_page_last o4332 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C11 H9 F2 N3 O' _chemical_formula_moiety 'C11 H9 F2 N3 O' _chemical_formula_sum 'C11 H9 F2 N3 O' _chemical_formula_weight 237.21 _chemical_name_systematic ; 1-(2,4-Difluorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-1-one ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 100.685(7) _cell_angle_beta 90.650(8) _cell_angle_gamma 110.307(7) _cell_formula_units_Z 2 _cell_length_a 6.939(3) _cell_length_b 7.743(4) _cell_length_c 10.939(5) _cell_measurement_reflns_used 1078 _cell_measurement_temperature 294(2) _cell_measurement_theta_max 25.11 _cell_measurement_theta_min 2.86 _cell_volume 539.8(4) _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_collection 'SMART (Bruker, 1997)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 294(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \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 0.0272 _diffrn_reflns_av_sigmaI/netI 0.0396 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 2748 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 1.90 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_T_max 0.9786 _exptl_absorpt_correction_T_min 0.9739 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 244 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.148 _refine_diff_density_min -0.209 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 1897 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.0653 _refine_ls_R_factor_gt 0.0408 _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^)+(0.0651P)^2^+0.0629P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1052 _refine_ls_wR_factor_ref 0.1256 _reflns_number_gt 1316 _reflns_number_total 1897 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bx2021.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2210529 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 F F1 1.0979(2) 0.8283(2) 0.25874(12) 0.0836(5) Uani d . 1 F F2 0.69642(18) 0.7072(2) 0.59045(12) 0.0820(5) Uani d . 1 O O1 1.1737(2) 0.6540(2) 0.78827(14) 0.0634(5) Uani d . 1 N N1 0.7466(2) 0.7335(2) 1.03285(15) 0.0457(4) Uani d . 1 N N2 0.6820(3) 0.8788(3) 1.03009(18) 0.0628(5) Uani d . 1 N N3 0.5215(3) 0.7153(3) 1.17180(16) 0.0583(5) Uani d . 1 C C1 1.2269(3) 0.7551(3) 0.55853(19) 0.0536(6) Uani d . 1 H H1 1.3393 0.7497 0.6027 0.064 Uiso calc R 1 C C2 1.2476(3) 0.7884(3) 0.4392(2) 0.0603(6) Uani d . 1 H H2 1.3719 0.8064 0.4030 0.072 Uiso calc R 1 C C3 1.0804(4) 0.7941(3) 0.37577(19) 0.0561(6) Uani d . 1 C C4 0.8948(3) 0.7666(3) 0.42434(19) 0.0577(6) Uani d . 1 H H4 0.7824 0.7693 0.3787 0.069 Uiso calc R 1 C C5 0.8814(3) 0.7349(3) 0.54373(19) 0.0499(5) Uani d . 1 C C6 1.0432(3) 0.7292(3) 0.61525(17) 0.0428(5) Uani d . 1 C C7 1.0369(3) 0.6947(3) 0.74592(18) 0.0443(5) Uani d . 1 C C8 0.8671(3) 0.7154(3) 0.82318(18) 0.0490(5) Uani d . 1 H H8A 0.7381 0.6172 0.7877 0.059 Uiso calc R 1 H H8B 0.8541 0.8356 0.8212 0.059 Uiso calc R 1 C C9 0.9066(3) 0.7037(3) 0.95630(19) 0.0517(5) Uani d . 1 H H9A 0.9124 0.5810 0.9586 0.062 Uiso calc R 1 H H9B 1.0391 0.7977 0.9904 0.062 Uiso calc R 1 C C10 0.5487(4) 0.8604(3) 1.1145(2) 0.0612(6) Uani d . 1 H H10 0.4772 0.9424 1.1337 0.073 Uiso calc R 1 C C11 0.6498(3) 0.6397(3) 1.11675(19) 0.0522(5) Uani d . 1 H H11 0.6695 0.5340 1.1347 0.063 Uiso calc R 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 0.0919(11) 0.1147(12) 0.0499(8) 0.0371(9) 0.0187(7) 0.0288(8) F2 0.0476(7) 0.1512(15) 0.0606(9) 0.0473(9) 0.0130(6) 0.0298(9) O1 0.0668(10) 0.0854(12) 0.0583(10) 0.0496(9) 0.0095(8) 0.0196(8) N1 0.0449(9) 0.0536(10) 0.0445(9) 0.0201(8) 0.0097(7) 0.0181(8) N2 0.0702(12) 0.0604(12) 0.0748(13) 0.0348(10) 0.0296(10) 0.0308(10) N3 0.0612(11) 0.0711(13) 0.0494(10) 0.0272(10) 0.0172(9) 0.0208(9) C1 0.0436(11) 0.0660(14) 0.0544(13) 0.0246(10) 0.0071(10) 0.0097(10) C2 0.0494(12) 0.0746(16) 0.0562(14) 0.0201(11) 0.0191(11) 0.0143(11) C3 0.0648(14) 0.0603(14) 0.0428(12) 0.0213(11) 0.0119(10) 0.0103(10) C4 0.0598(14) 0.0722(15) 0.0443(12) 0.0300(12) 0.0001(10) 0.0066(10) C5 0.0410(11) 0.0622(14) 0.0479(12) 0.0220(10) 0.0093(9) 0.0068(10) C6 0.0412(10) 0.0428(11) 0.0444(11) 0.0169(8) 0.0073(9) 0.0045(8) C7 0.0436(11) 0.0416(11) 0.0488(12) 0.0176(9) 0.0047(9) 0.0072(9) C8 0.0454(11) 0.0580(13) 0.0484(12) 0.0218(10) 0.0096(9) 0.0158(10) C9 0.0494(11) 0.0629(13) 0.0523(12) 0.0275(10) 0.0108(10) 0.0192(10) C10 0.0646(14) 0.0630(14) 0.0657(15) 0.0313(12) 0.0234(12) 0.0184(12) C11 0.0569(12) 0.0604(13) 0.0455(12) 0.0229(11) 0.0061(10) 0.0211(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C11 N1 N2 109.16(17) C11 N1 C9 129.11(18) N2 N1 C9 121.65(15) C10 N2 N1 102.32(16) C11 N3 C10 101.58(17) C2 C1 C6 122.2(2) C2 C1 H1 118.9 C6 C1 H1 118.9 C3 C2 C1 117.95(19) C3 C2 H2 121.0 C1 C2 H2 121.0 F1 C3 C4 117.9(2) F1 C3 C2 118.94(19) C4 C3 C2 123.2(2) C3 C4 C5 116.9(2) C3 C4 H4 121.6 C5 C4 H4 121.6 F2 C5 C4 116.24(18) F2 C5 C6 119.93(18) C4 C5 C6 123.84(19) C5 C6 C1 115.97(18) C5 C6 C7 126.00(17) C1 C6 C7 118.02(17) O1 C7 C8 120.79(18) O1 C7 C6 118.90(17) C8 C7 C6 120.29(17) C7 C8 C9 111.67(17) C7 C8 H8A 109.3 C9 C8 H8A 109.3 C7 C8 H8B 109.3 C9 C8 H8B 109.3 H8A C8 H8B 107.9 N1 C9 C8 111.59(16) N1 C9 H9A 109.3 C8 C9 H9A 109.3 N1 C9 H9B 109.3 C8 C9 H9B 109.3 H9A C9 H9B 108.0 N2 C10 N3 115.6(2) N2 C10 H10 122.2 N3 C10 H10 122.2 N3 C11 N1 111.30(19) N3 C11 H11 124.4 N1 C11 H11 124.4 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F1 C3 1.353(2) F2 C5 1.349(2) O1 C7 1.212(2) N1 C11 1.320(3) N1 N2 1.352(2) N1 C9 1.455(3) N2 C10 1.306(3) N3 C11 1.319(3) N3 C10 1.345(3) C1 C2 1.376(3) C1 C6 1.391(3) C1 H1 0.9300 C2 C3 1.363(3) C2 H2 0.9300 C3 C4 1.361(3) C4 C5 1.371(3) C4 H4 0.9300 C5 C6 1.379(3) C6 C7 1.500(3) C7 C8 1.493(3) C8 C9 1.504(3) C8 H8A 0.9700 C8 H8B 0.9700 C9 H9A 0.9700 C9 H9B 0.9700 C10 H10 0.9300 C11 H11 0.9300 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C11 H11 O1 2_767 0.93 2.355 3.245(3) 160.3(2) no 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 C11 N1 N2 C10 0.0(2) C9 N1 N2 C10 -177.00(19) C6 C1 C2 C3 -0.5(3) C1 C2 C3 F1 179.41(19) C1 C2 C3 C4 -0.7(4) F1 C3 C4 C5 -179.10(19) C2 C3 C4 C5 1.0(3) C3 C4 C5 F2 -179.74(18) C3 C4 C5 C6 -0.1(3) F2 C5 C6 C1 178.62(18) C4 C5 C6 C1 -1.0(3) F2 C5 C6 C7 -0.3(3) C4 C5 C6 C7 -179.90(19) C2 C1 C6 C5 1.3(3) C2 C1 C6 C7 -179.68(19) C5 C6 C7 O1 164.5(2) C1 C6 C7 O1 -14.4(3) C5 C6 C7 C8 -17.0(3) C1 C6 C7 C8 164.08(18) O1 C7 C8 C9 7.1(3) C6 C7 C8 C9 -171.35(17) C11 N1 C9 C8 135.7(2) N2 N1 C9 C8 -47.9(3) C7 C8 C9 N1 177.03(16) N1 N2 C10 N3 0.0(3) C11 N3 C10 N2 -0.1(3) C10 N3 C11 N1 0.1(2) N2 N1 C11 N3 -0.1(3) C9 N1 C11 N3 176.66(18) _cod_database_fobs_code 2210529 _journal_paper_doi 10.1107/S1600536806035215