#------------------------------------------------------------------------------ #$Date: 2015-01-07 16:25:02 +0000 (Wed, 07 Jan 2015) $ #$Revision: 129439 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/45/2204564.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_2204564 loop_ _publ_author_name 'Liangzhong Xu' 'Chongyi Zhu' 'Yongqi Qin' 'Guanping Yu' 'Guodong Si' _publ_section_title ; (4-Fluorobenzoyl)(1H-1,2,4-triazol-1-yl)methyl morpholine-4-carbodithioate ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o2099 _journal_page_last o2100 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C15 H15 F N4 O2 S2' _chemical_formula_moiety 'C15 H15 F N4 O2 S2' _chemical_formula_sum 'C15 H15 F N4 O2 S2' _chemical_formula_weight 366.45 _chemical_name_systematic ; (4-Fluorobenzoyl)(1H-1,2,4-triazol-1-yl)methyl morpholine-4-carbodithioate ; _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 79.23(3) _cell_angle_beta 81.42(3) _cell_angle_gamma 68.91(3) _cell_formula_units_Z 2 _cell_length_a 7.508(2) _cell_length_b 7.605(2) _cell_length_c 16.271(3) _cell_measurement_reflns_used 20 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 11 _cell_measurement_theta_min 2 _cell_volume 848.1(4) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1990)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type ; Siemens 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 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0743 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 4932 _diffrn_reflns_theta_full 26.39 _diffrn_reflns_theta_max 26.39 _diffrn_reflns_theta_min 2.56 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.340 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_meas ? _exptl_crystal_density_method . _exptl_crystal_description block _exptl_crystal_F_000 380 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.312 _refine_diff_density_min -0.199 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 217 _refine_ls_number_reflns 3441 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.004 _refine_ls_R_factor_all 0.1083 _refine_ls_R_factor_gt 0.0529 _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^)+(0.0442P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0955 _refine_ls_wR_factor_ref 0.1119 _reflns_number_gt 2060 _reflns_number_total 3441 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file rz6007.cif _[local]_cod_data_source_block I _cod_database_code 2204564 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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' S S 0.1246 0.1234 '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_ _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 0.8334(4) -0.3755(3) 0.57762(16) 0.1234(10) Uani d . 1 F S1 0.80769(10) 0.12726(13) 0.14103(5) 0.0528(3) Uani d . 1 S S2 0.92595(10) 0.34443(12) 0.24833(5) 0.0471(2) Uani d . 1 S O1 0.6520(4) 0.4788(3) 0.41874(13) 0.0703(7) Uani d . 1 O O2 1.4104(3) 0.2873(3) -0.01068(13) 0.0643(6) Uani d . 1 O N1 0.5457(3) 0.5461(4) 0.26046(14) 0.0468(6) Uani d . 1 N N2 0.3730(4) 0.5543(4) 0.24285(18) 0.0679(8) Uani d . 1 N N3 0.3812(5) 0.8496(5) 0.23571(19) 0.0785(9) Uani d . 1 N N4 1.1187(3) 0.2256(3) 0.11104(13) 0.0404(6) Uani d . 1 N C1 0.2832(6) 0.7391(6) 0.2286(2) 0.0809(12) Uani d . 1 C H1A 0.1575 0.7901 0.2142 0.097 Uiso calc R 1 H C2 0.5456(6) 0.7224(5) 0.2564(2) 0.0671(10) Uani d . 1 C H2A 0.6493 0.7518 0.2669 0.081 Uiso calc R 1 H C3 0.6842(4) 0.3643(4) 0.29037(16) 0.0401(7) Uani d . 1 C H3A 0.6516 0.2615 0.2751 0.048 Uiso calc R 1 H C4 0.6865(4) 0.3381(4) 0.38609(17) 0.0435(7) Uani d . 1 C C5 0.7304(4) 0.1449(4) 0.43455(18) 0.0433(7) Uani d . 1 C C6 0.7884(5) -0.0175(5) 0.3964(2) 0.0626(9) Uani d . 1 C H6A 0.8022 -0.0076 0.3381 0.075 Uiso calc R 1 H C7 0.8257(6) -0.1937(5) 0.4448(3) 0.0821(12) Uani d . 1 C H7A 0.8672 -0.3038 0.4199 0.099 Uiso calc R 1 H C8 0.8007(6) -0.2036(6) 0.5297(3) 0.0739(11) Uani d . 1 C C9 0.7455(5) -0.0491(6) 0.5695(2) 0.0736(11) Uani d . 1 C H9A 0.7308 -0.0612 0.6278 0.088 Uiso calc R 1 H C10 0.7116(4) 0.1264(5) 0.5212(2) 0.0610(9) Uani d . 1 C H10A 0.6755 0.2345 0.5473 0.073 Uiso calc R 1 H C11 0.9592(4) 0.2262(4) 0.15865(16) 0.0356(6) Uani d . 1 C C12 1.2628(4) 0.2958(4) 0.13155(17) 0.0472(8) Uani d . 1 C H12B 1.3687 0.1892 0.1546 0.057 Uiso calc R 1 H H12A 1.2064 0.3798 0.1737 0.057 Uiso calc R 1 H C13 1.3357(4) 0.4013(5) 0.05449(19) 0.0556(8) Uani d . 1 C H13B 1.2319 0.5149 0.0349 0.067 Uiso calc R 1 H H13A 1.4352 0.4410 0.0686 0.067 Uiso calc R 1 H C14 1.2647(5) 0.2340(5) -0.03323(19) 0.0626(9) Uani d . 1 C H14B 1.3158 0.1594 -0.0790 0.075 Uiso calc R 1 H H14A 1.1616 0.3478 -0.0531 0.075 Uiso calc R 1 H C15 1.1861(4) 0.1205(5) 0.03833(18) 0.0523(8) Uani d . 1 C H15B 1.0806 0.0951 0.0211 0.063 Uiso calc R 1 H H15A 1.2849 -0.0006 0.0541 0.063 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 0.174(3) 0.0761(18) 0.112(2) -0.0467(18) -0.0487(18) 0.0415(15) S1 0.0402(4) 0.0713(6) 0.0589(5) -0.0264(4) 0.0037(4) -0.0299(4) S2 0.0444(5) 0.0627(6) 0.0433(5) -0.0266(4) 0.0065(3) -0.0212(4) O1 0.1060(19) 0.0528(16) 0.0501(14) -0.0226(14) 0.0065(12) -0.0222(11) O2 0.0562(14) 0.0826(18) 0.0593(15) -0.0348(13) 0.0217(11) -0.0216(12) N1 0.0483(16) 0.0428(17) 0.0477(15) -0.0141(13) -0.0003(12) -0.0091(11) N2 0.0526(18) 0.058(2) 0.089(2) -0.0117(16) -0.0128(15) -0.0120(16) N3 0.094(3) 0.051(2) 0.076(2) -0.006(2) -0.0157(18) -0.0057(16) N4 0.0389(13) 0.0475(16) 0.0398(14) -0.0201(12) 0.0033(11) -0.0131(11) C1 0.070(3) 0.062(3) 0.093(3) 0.002(2) -0.020(2) -0.006(2) C2 0.084(3) 0.049(2) 0.072(2) -0.027(2) -0.012(2) -0.0044(18) C3 0.0397(16) 0.0389(19) 0.0427(17) -0.0150(14) 0.0032(13) -0.0105(13) C4 0.0412(17) 0.048(2) 0.0425(18) -0.0170(15) 0.0067(13) -0.0144(15) C5 0.0364(16) 0.046(2) 0.0470(19) -0.0144(14) -0.0003(13) -0.0078(14) C6 0.087(3) 0.054(2) 0.054(2) -0.031(2) -0.0116(18) -0.0056(17) C7 0.120(3) 0.049(3) 0.086(3) -0.032(2) -0.035(2) -0.003(2) C8 0.083(3) 0.062(3) 0.074(3) -0.029(2) -0.027(2) 0.021(2) C9 0.072(3) 0.077(3) 0.052(2) -0.008(2) -0.0093(18) 0.005(2) C10 0.057(2) 0.060(2) 0.051(2) -0.0026(18) -0.0001(15) -0.0090(17) C11 0.0309(15) 0.0369(17) 0.0377(16) -0.0096(13) -0.0004(12) -0.0081(12) C12 0.0397(17) 0.058(2) 0.0480(18) -0.0221(16) 0.0012(13) -0.0101(15) C13 0.0522(19) 0.059(2) 0.059(2) -0.0272(17) 0.0068(15) -0.0085(16) C14 0.055(2) 0.085(3) 0.049(2) -0.026(2) 0.0125(16) -0.0228(18) C15 0.0460(18) 0.061(2) 0.0529(19) -0.0191(16) 0.0120(15) -0.0280(16) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag F1 C8 1.350(4) yes S1 C11 1.654(3) yes S2 C11 1.794(3) yes S2 C3 1.805(3) yes O1 C4 1.211(3) yes O2 C14 1.411(3) yes O2 C13 1.417(3) yes N1 C2 1.330(4) ? N1 N2 1.347(3) ? N1 C3 1.447(4) ? N2 C1 1.314(4) ? N3 C2 1.310(4) ? N3 C1 1.329(4) ? N4 C11 1.325(3) yes N4 C12 1.469(3) yes N4 C15 1.476(3) yes C1 H1A 0.9300 ? C2 H2A 0.9300 ? C3 C4 1.535(4) ? C3 H3A 0.9800 ? C4 C5 1.478(4) ? C5 C10 1.382(4) ? C5 C6 1.386(4) ? C6 C7 1.377(5) ? C6 H6A 0.9300 ? C7 C8 1.356(5) ? C7 H7A 0.9300 ? C8 C9 1.351(5) ? C9 C10 1.373(5) ? C9 H9A 0.9300 ? C10 H10A 0.9300 ? C12 C13 1.500(4) ? C12 H12B 0.9700 ? C12 H12A 0.9700 ? C13 H13B 0.9700 ? C13 H13A 0.9700 ? C14 C15 1.495(4) ? C14 H14B 0.9700 ? C14 H14A 0.9700 ? C15 H15B 0.9700 ? C15 H15A 0.9700 ? 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 C11 S2 C3 102.86(12) ? C14 O2 C13 109.5(2) yes C2 N1 N2 109.0(3) ? C2 N1 C3 130.7(3) ? N2 N1 C3 119.6(3) ? C1 N2 N1 101.5(3) ? C2 N3 C1 101.3(3) ? C11 N4 C12 125.1(2) yes C11 N4 C15 121.8(2) yes C12 N4 C15 112.2(2) yes N2 C1 N3 116.6(4) ? N2 C1 H1A 121.7 ? N3 C1 H1A 121.7 ? N3 C2 N1 111.5(3) ? N3 C2 H2A 124.2 ? N1 C2 H2A 124.2 ? N1 C3 C4 110.9(2) ? N1 C3 S2 112.3(2) ? C4 C3 S2 105.33(18) ? N1 C3 H3A 109.4 ? C4 C3 H3A 109.4 ? S2 C3 H3A 109.4 ? O1 C4 C5 122.7(3) ? O1 C4 C3 117.8(3) ? C5 C4 C3 119.5(2) ? C10 C5 C6 119.0(3) ? C10 C5 C4 118.5(3) ? C6 C5 C4 122.5(3) ? C7 C6 C5 119.9(3) ? C7 C6 H6A 120.0 ? C5 C6 H6A 120.0 ? C8 C7 C6 118.8(3) ? C8 C7 H7A 120.6 ? C6 C7 H7A 120.6 ? F1 C8 C9 117.6(4) ? F1 C8 C7 119.1(4) ? C9 C8 C7 123.3(4) ? C8 C9 C10 118.0(4) ? C8 C9 H9A 121.0 ? C10 C9 H9A 121.0 ? C9 C10 C5 121.0(3) ? C9 C10 H10A 119.5 ? C5 C10 H10A 119.5 ? N4 C11 S1 125.4(2) ? N4 C11 S2 111.93(19) ? S1 C11 S2 122.67(15) ? N4 C12 C13 110.4(2) ? N4 C12 H12B 109.6 ? C13 C12 H12B 109.6 ? N4 C12 H12A 109.6 ? C13 C12 H12A 109.6 ? H12B C12 H12A 108.1 ? O2 C13 C12 111.7(3) ? O2 C13 H13B 109.3 ? C12 C13 H13B 109.3 ? O2 C13 H13A 109.3 ? C12 C13 H13A 109.3 ? H13B C13 H13A 107.9 ? O2 C14 C15 112.5(3) ? O2 C14 H14B 109.1 ? C15 C14 H14B 109.1 ? O2 C14 H14A 109.1 ? C15 C14 H14A 109.1 ? H14B C14 H14A 107.8 ? N4 C15 C14 110.3(2) ? N4 C15 H15B 109.6 ? C14 C15 H15B 109.6 ? N4 C15 H15A 109.6 ? C14 C15 H15A 109.6 ? H15B C15 H15A 108.1 ? 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 C3 H3A S1 ? 0.98 2.53 3.127(3) 119 yes C12 H12A S2 ? 0.97 2.35 2.881(3) 114 yes C12 H12A N2 1_655 0.97 2.60 3.283(4) 128 yes C15 H15B S1 ? 0.97 2.59 3.062(3) 110 yes _journal_paper_doi 10.1107/S1600536804026017