#------------------------------------------------------------------------------ #$Date: 2011-01-02 20:00:31 +0000 (Sun, 02 Jan 2011) $ #$Revision: 5310 $ #$URL: svn://www.crystallography.net/cod/cif/2/2206924.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_2206924 loop_ _publ_author_name 'Jun Wan' 'Chun-Li Li' 'Xue-Mei Li' 'Shu-Sheng Zhang' 'Ping-Kai Ouyang' _publ_section_title ; 1-(4-Nitrophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-1-one ; _journal_coeditor_code CV6563 _journal_issue 10 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o3394 _journal_page_last o3395 _journal_volume 61 _journal_year 2005 _chemical_formula_moiety 'C11 H10 N4 O3' _chemical_formula_sum 'C11 H10 N4 O3' _chemical_formula_weight 246.23 _chemical_name_systematic ; 1-(4-Nitrophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-1-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 geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 103.233(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.8529(7) _cell_length_b 5.4011(4) _cell_length_c 21.9132(14) _cell_measurement_reflns_used 2976 _cell_measurement_temperature 294(2) _cell_measurement_theta_max 26.0 _cell_measurement_theta_min 2.5 _cell_volume 1135.18(14) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003) ; _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 294(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type ; Simens SMART 1000 CCD area detector diffractometer ; _diffrn_measurement_method '\w scans' _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 0.0145 _diffrn_reflns_av_sigmaI/netI 0.0152 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 6034 _diffrn_reflns_theta_full 26.04 _diffrn_reflns_theta_max 26.04 _diffrn_reflns_theta_min 1.91 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_correction_T_min 0.943 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 512 _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.170 _refine_diff_density_min -0.193 _refine_ls_extinction_coef 0.030(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 174 _refine_ls_number_reflns 2231 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.032 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0409 _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^)+(0.0627P)^2^+0.1874P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1111 _refine_ls_wR_factor_ref 0.1157 _reflns_number_gt 1956 _reflns_number_total 2231 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cv6563.cif _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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 ; _cod_database_code 2206924 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 O1 0.89452(12) -0.2351(3) 0.02312(7) 0.1040(5) Uani d . 1 O O2 0.70365(13) -0.0889(3) 0.03977(6) 0.0834(4) Uani d . 1 O O3 0.52640(11) -1.0409(2) -0.19541(6) 0.0763(4) Uani d . 1 O N1 0.76753(13) -0.2293(3) 0.01285(6) 0.0669(4) Uani d . 1 N N2 0.12801(11) -0.9109(2) -0.30104(5) 0.0517(3) Uani d . 1 N N3 0.09999(13) -0.6937(3) -0.33185(7) 0.0690(4) Uani d . 1 N N4 -0.09294(14) -0.9264(3) -0.34626(8) 0.0811(5) Uani d . 1 N C1 0.68188(14) -0.7488(3) -0.10050(7) 0.0564(4) Uani d . 1 C H1A 0.7258 -0.8828 -0.1144 0.063(4) Uiso d R 1 H C2 0.75692(14) -0.5941(3) -0.05504(7) 0.0595(4) Uani d . 1 C H2A 0.8514 -0.6207 -0.0385 0.071(5) Uiso d R 1 H C3 0.68863(14) -0.3993(3) -0.03473(6) 0.0548(4) Uani d . 1 C C4 0.54824(14) -0.3547(3) -0.05758(7) 0.0553(4) Uani d . 1 C H4B 0.5043 -0.2239 -0.0423 0.066(4) Uiso d R 1 H C5 0.47466(13) -0.5088(3) -0.10371(6) 0.0520(3) Uani d . 1 C H5A 0.3803 -0.4804 -0.1202 0.059(4) Uiso d R 1 H C6 0.54032(13) -0.7058(3) -0.12578(6) 0.0479(3) Uani d . 1 C C7 0.46646(13) -0.8693(3) -0.17789(6) 0.0506(3) Uani d . 1 C C8 0.31662(13) -0.8150(3) -0.20892(6) 0.0535(4) Uani d . 1 C H8A 0.2584 -0.8475 -0.1796 0.068(5) Uiso d R 1 H H8B 0.3070 -0.6414 -0.2205 0.073(5) Uiso d R 1 H C9 0.26867(14) -0.9722(3) -0.26654(7) 0.0590(4) Uani d . 1 C H9A 0.3325 -0.9505 -0.2939 0.078(5) Uiso d R 1 H H9B 0.2715 -1.1450 -0.2543 0.075(5) Uiso d R 1 H C10 0.01315(16) -1.0436(3) -0.31051(8) 0.0714(5) Uani d . 1 C H10A 0.0076 -1.2009 -0.2940 0.091(6) Uiso d R 1 H C11 -0.03301(16) -0.7159(3) -0.35809(8) 0.0707(5) Uani d . 1 C H11A -0.0825 -0.5926 -0.3834 0.097(6) Uiso d 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 O1 0.0535(7) 0.1390(13) 0.1094(11) -0.0130(8) -0.0024(7) -0.0372(10) O2 0.0751(8) 0.0908(9) 0.0799(8) -0.0060(7) 0.0090(6) -0.0226(7) O3 0.0602(6) 0.0731(7) 0.0869(8) 0.0225(6) -0.0012(5) -0.0157(6) N1 0.0576(8) 0.0789(9) 0.0590(7) -0.0087(7) 0.0025(6) 0.0014(7) N2 0.0465(6) 0.0490(6) 0.0562(7) -0.0018(5) 0.0050(5) -0.0005(5) N3 0.0562(7) 0.0634(8) 0.0806(9) -0.0065(6) 0.0016(6) 0.0171(7) N4 0.0533(7) 0.0877(11) 0.0908(10) -0.0159(7) -0.0070(7) 0.0108(8) C1 0.0454(7) 0.0646(9) 0.0572(8) 0.0091(6) 0.0078(6) 0.0071(7) C2 0.0408(7) 0.0758(10) 0.0579(8) 0.0036(7) 0.0032(6) 0.0089(7) C3 0.0499(7) 0.0640(9) 0.0482(7) -0.0061(6) 0.0063(6) 0.0073(6) C4 0.0491(7) 0.0619(9) 0.0540(8) 0.0024(6) 0.0101(6) 0.0014(6) C5 0.0401(6) 0.0610(8) 0.0531(7) 0.0032(6) 0.0071(5) 0.0056(6) C6 0.0421(7) 0.0541(8) 0.0470(7) 0.0033(5) 0.0092(5) 0.0102(6) C7 0.0455(7) 0.0524(8) 0.0537(7) 0.0066(6) 0.0106(6) 0.0077(6) C8 0.0434(7) 0.0614(9) 0.0540(8) 0.0055(6) 0.0076(6) -0.0024(6) C9 0.0497(8) 0.0568(9) 0.0659(9) 0.0064(6) 0.0039(6) -0.0067(7) C10 0.0613(9) 0.0623(10) 0.0826(11) -0.0169(8) 0.0000(8) 0.0075(8) C11 0.0577(9) 0.0764(11) 0.0694(10) 0.0013(8) -0.0033(7) 0.0137(8) 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' 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 O2 N1 O1 123.21(15) ? O2 N1 C3 118.90(13) ? O1 N1 C3 117.89(15) ? C10 N2 N3 108.93(12) yes C10 N2 C9 129.78(13) yes N3 N2 C9 121.23(12) ? C11 N3 N2 102.09(12) yes C10 N4 C11 101.48(13) yes C2 C1 C6 120.48(14) ? C2 C1 H1A 119.8 ? C6 C1 H1A 119.8 ? C3 C2 C1 118.42(13) ? C3 C2 H2A 120.8 ? C1 C2 H2A 120.8 ? C2 C3 C4 122.67(14) ? C2 C3 N1 119.23(13) ? C4 C3 N1 118.10(14) ? C5 C4 C3 118.37(14) ? C5 C4 H4B 120.8 ? C3 C4 H4B 120.8 ? C4 C5 C6 120.58(12) ? C4 C5 H5A 119.7 ? C6 C5 H5A 119.7 ? C5 C6 C1 119.46(13) ? C5 C6 C7 122.34(11) ? C1 C6 C7 118.15(12) ? O3 C7 C6 120.56(12) ? O3 C7 C8 120.40(13) ? C6 C7 C8 119.03(12) yes C9 C8 C7 110.85(11) yes C9 C8 H8A 109.5 ? C7 C8 H8A 109.5 ? C9 C8 H8B 109.5 ? C7 C8 H8B 109.5 ? H8A C8 H8B 108.1 ? N2 C9 C8 112.69(11) yes N2 C9 H9A 109.0 ? C8 C9 H9A 109.1 ? N2 C9 H9B 109.1 ? C8 C9 H9B 109.1 ? H9A C9 H9B 107.8 ? N2 C10 N4 111.67(15) ? N2 C10 H10A 124.2 ? N4 C10 H10A 124.2 ? N3 C11 N4 115.82(15) ? N3 C11 H11A 122.1 ? N4 C11 H11A 122.1 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 N1 1.2200(16) ? O2 N1 1.2201(18) ? O3 C7 1.2077(17) yes N1 C3 1.471(2) yes N2 C10 1.3153(18) yes N2 N3 1.3499(17) yes N2 C9 1.4568(17) yes N3 C11 1.3104(19) yes N4 C10 1.316(2) yes N4 C11 1.334(2) yes C1 C2 1.378(2) ? C1 C6 1.3973(18) ? C1 H1A 0.9299 ? C2 C3 1.376(2) ? C2 H2A 0.9300 ? C3 C4 1.3803(19) ? C4 C5 1.380(2) ? C4 H4B 0.9300 ? C5 C6 1.3886(19) ? C5 H5A 0.9300 ? C6 C7 1.494(2) ? C7 C8 1.5062(18) ? C8 C9 1.505(2) ? C8 H8A 0.9700 ? C8 H8B 0.9700 ? C9 H9A 0.9701 ? C9 H9B 0.9699 ? C10 H10A 0.9300 ? C11 H11A 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 C2 H2A O1 3_745 0.93 2.57 3.469(2) 163 yes C11 H11A O2 4_455 0.93 2.57 3.435(2) 154 yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion C10 N2 N3 C11 -0.23(18) C9 N2 N3 C11 177.40(13) C6 C1 C2 C3 0.9(2) C1 C2 C3 C4 0.7(2) C1 C2 C3 N1 -178.79(13) O2 N1 C3 C2 -165.50(14) O1 N1 C3 C2 14.9(2) O2 N1 C3 C4 15.0(2) O1 N1 C3 C4 -164.54(15) C2 C3 C4 C5 -1.6(2) N1 C3 C4 C5 177.91(13) C3 C4 C5 C6 0.9(2) C4 C5 C6 C1 0.6(2) C4 C5 C6 C7 -176.82(12) C2 C1 C6 C5 -1.5(2) C2 C1 C6 C7 176.02(13) C5 C6 C7 O3 -179.13(13) C1 C6 C7 O3 3.5(2) C5 C6 C7 C8 1.75(19) C1 C6 C7 C8 -175.67(12) O3 C7 C8 C9 -8.5(2) C6 C7 C8 C9 170.63(12) C10 N2 C9 C8 -113.84(18) N3 N2 C9 C8 69.08(18) C7 C8 C9 N2 -175.10(12) N3 N2 C10 N4 -0.3(2) C9 N2 C10 N4 -177.70(15) C11 N4 C10 N2 0.7(2) N2 N3 C11 N4 0.7(2) C10 N4 C11 N3 -0.9(2)