#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/50/2205079.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_2205079 loop_ _publ_author_name 'Liu, Fa-Qian' 'Li, Wei-Hua' 'Lu, Lu-De' 'Yang, Xu-Jie' 'Wang, Xin' 'Bao-Rong Hou' _publ_section_title ; 2-(Benzotriazol-1-yl)-2-(\a-hydroxybenzyl)-N-phenylthioacrylamide ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o208 _journal_page_last o209 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C21 H16 N4 O S' _chemical_formula_moiety 'C21 H16 N4 O S' _chemical_formula_sum 'C21 H16 N4 O S' _chemical_formula_weight 372.45 _chemical_name_systematic ; 2-(Benzotriazol-1-yl)-2-(\a-hydroxybenzyl)-N-phenylthioacrylamide ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 90.315(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 19.089(3) _cell_length_b 8.4715(11) _cell_length_c 23.161(3) _cell_measurement_reflns_used 2238 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 22.60 _cell_measurement_theta_min 2.63 _cell_volume 3745.4(9) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1999)' _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 293(2) _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _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 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_number 12321 _diffrn_reflns_theta_full 28.02 _diffrn_reflns_theta_max 28.02 _diffrn_reflns_theta_min 2.13 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.191 _exptl_absorpt_correction_T_max 0.966 _exptl_absorpt_correction_T_min 0.892 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1552 _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.160 _refine_diff_density_min -0.178 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 252 _refine_ls_number_reflns 4500 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.060 _refine_ls_R_factor_all 0.0772 _refine_ls_R_factor_gt 0.0395 _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^)+(0.0561P)^2^+0.3455P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1070 _refine_ls_wR_factor_ref 0.1208 _reflns_number_gt 2680 _reflns_number_total 4500 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file hg6121.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'C 2/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 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_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2205079 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -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 S1 0.24742(3) 0.07308(7) 0.21558(2) 0.07351(19) Uani d . 1 S N1 0.35250(7) 0.21193(16) 0.26950(6) 0.0484(3) Uani d D 1 N H1 0.3882(6) 0.2729(16) 0.2707(6) 0.047(5) Uiso d D 1 H N2 0.41692(7) 0.33361(15) 0.17503(5) 0.0448(3) Uani d . 1 N N3 0.48164(7) 0.27141(16) 0.18477(5) 0.0520(3) Uani d . 1 N N4 0.52655(7) 0.38526(17) 0.18781(6) 0.0534(4) Uani d . 1 N O1 0.28639(8) 0.10816(18) 0.09654(6) 0.0781(4) Uani d D 1 O H1A 0.2628(15) 0.090(4) 0.1282(9) 0.161(14) Uiso d D 1 H C1 0.32212(8) 0.17782(18) 0.21948(7) 0.0496(4) Uani d . 1 C C2 0.35720(8) 0.23343(18) 0.16755(7) 0.0489(4) Uani d . 1 C C3 0.34178(9) 0.19361(19) 0.11193(7) 0.0556(4) Uani d . 1 C C4 0.38581(10) 0.2418(2) 0.06241(7) 0.0568(4) Uani d . 1 C C5 0.36006(13) 0.3431(2) 0.02104(9) 0.0826(6) Uani d . 1 C H5 0.3146 0.3818 0.0237 0.099 Uiso calc R 1 H C6 0.40242(16) 0.3872(3) -0.02467(10) 0.0964(8) Uani d . 1 C H6 0.3855 0.4573 -0.0523 0.116 Uiso calc R 1 H C7 0.46866(15) 0.3287(3) -0.02943(9) 0.0929(7) Uani d . 1 C H7 0.4971 0.3605 -0.0598 0.111 Uiso calc R 1 H C8 0.49289(13) 0.2246(3) 0.00995(9) 0.0906(7) Uani d . 1 C H8 0.5374 0.1817 0.0059 0.109 Uiso calc R 1 H C9 0.45214(12) 0.1819(3) 0.05592(8) 0.0780(6) Uani d . 1 C H9 0.4697 0.1113 0.0831 0.094 Uiso calc R 1 H C10 0.42170(8) 0.49442(18) 0.17111(6) 0.0446(4) Uani d . 1 C C11 0.49238(8) 0.52626(19) 0.17947(6) 0.0466(4) Uani d . 1 C C12 0.51744(11) 0.6803(2) 0.17999(7) 0.0628(5) Uani d . 1 C H12 0.5646 0.7026 0.1861 0.075 Uiso calc R 1 H C13 0.46967(14) 0.7967(2) 0.17111(8) 0.0783(6) Uani d . 1 C H13 0.4845 0.9013 0.1712 0.094 Uiso calc R 1 H C14 0.39901(13) 0.7632(2) 0.16190(9) 0.0796(6) Uani d . 1 C H14 0.3682 0.8467 0.1559 0.096 Uiso calc R 1 H C15 0.37307(10) 0.6131(2) 0.16130(8) 0.0640(5) Uani d . 1 C H15 0.3259 0.5918 0.1547 0.077 Uiso calc R 1 H C16 0.33475(8) 0.15150(19) 0.32506(7) 0.0489(4) Uani d . 1 C C17 0.33230(10) -0.0080(2) 0.33510(9) 0.0702(5) Uani d . 1 C H17 0.3377 -0.0790 0.3048 0.084 Uiso calc R 1 H C18 0.32177(12) -0.0623(3) 0.39046(12) 0.0914(7) Uani d . 1 C H18 0.3200 -0.1703 0.3974 0.110 Uiso calc R 1 H C19 0.31393(12) 0.0404(3) 0.43522(10) 0.0899(7) Uani d . 1 C H19 0.3077 0.0025 0.4725 0.108 Uiso calc R 1 H C20 0.31529(12) 0.1989(3) 0.42518(9) 0.0833(6) Uani d . 1 C H20 0.3089 0.2695 0.4555 0.100 Uiso calc R 1 H C21 0.32614(9) 0.2545(2) 0.36987(7) 0.0641(5) Uani d . 1 C H21 0.3276 0.3627 0.3631 0.077 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 S1 0.0610(3) 0.0871(4) 0.0724(3) -0.0280(3) -0.0011(2) -0.0015(3) N1 0.0459(8) 0.0501(8) 0.0493(8) -0.0084(6) 0.0023(6) 0.0029(6) N2 0.0439(8) 0.0476(8) 0.0429(7) -0.0004(6) 0.0013(5) 0.0008(6) N3 0.0490(8) 0.0568(8) 0.0501(8) 0.0049(7) 0.0000(6) 0.0006(6) N4 0.0473(8) 0.0628(9) 0.0501(8) 0.0001(7) 0.0024(6) 0.0017(7) O1 0.0797(10) 0.0877(10) 0.0667(9) -0.0218(8) -0.0111(8) -0.0103(7) C1 0.0497(10) 0.0460(9) 0.0531(10) -0.0020(7) 0.0002(7) -0.0018(7) C2 0.0487(9) 0.0477(9) 0.0502(9) -0.0034(7) -0.0011(7) -0.0026(7) C3 0.0589(11) 0.0512(9) 0.0565(10) -0.0011(8) -0.0067(8) -0.0032(8) C4 0.0714(12) 0.0557(10) 0.0433(9) 0.0005(9) -0.0058(8) -0.0062(8) C5 0.1029(17) 0.0817(14) 0.0631(13) 0.0163(13) -0.0026(12) 0.0068(11) C6 0.139(2) 0.0902(17) 0.0602(14) 0.0073(16) -0.0059(15) 0.0167(12) C7 0.120(2) 0.1093(19) 0.0493(12) -0.0164(16) 0.0117(13) -0.0051(12) C8 0.0911(16) 0.124(2) 0.0570(13) 0.0126(15) 0.0116(11) -0.0041(13) C9 0.0870(15) 0.0913(15) 0.0557(12) 0.0199(12) 0.0051(10) 0.0045(11) C10 0.0515(10) 0.0472(9) 0.0353(8) 0.0014(7) 0.0061(6) 0.0026(6) C11 0.0517(10) 0.0549(9) 0.0332(8) -0.0027(8) 0.0058(7) 0.0027(7) C12 0.0752(13) 0.0657(11) 0.0477(10) -0.0219(10) 0.0087(8) 0.0053(9) C13 0.118(2) 0.0497(11) 0.0679(13) -0.0130(12) 0.0103(12) 0.0064(9) C14 0.1030(18) 0.0535(12) 0.0826(14) 0.0195(12) 0.0108(12) 0.0092(10) C15 0.0640(12) 0.0618(12) 0.0663(12) 0.0121(9) 0.0064(9) 0.0074(9) C16 0.0408(9) 0.0526(10) 0.0532(10) -0.0028(7) 0.0003(7) 0.0116(8) C17 0.0733(13) 0.0589(11) 0.0783(13) 0.0009(10) -0.0005(10) 0.0131(10) C18 0.0974(18) 0.0790(15) 0.0975(18) -0.0175(13) -0.0114(14) 0.0426(14) C19 0.0834(16) 0.123(2) 0.0634(14) -0.0265(14) -0.0053(11) 0.0395(15) C20 0.0911(16) 0.1038(18) 0.0550(12) -0.0114(13) 0.0089(10) 0.0093(12) C21 0.0751(13) 0.0628(11) 0.0544(11) -0.0013(9) 0.0051(9) 0.0066(9) 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' 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 C1 N1 C16 127.26(14) no C1 N1 H1 120.4(10) no C16 N1 H1 112.3(10) no N3 N2 C10 109.61(12) no N3 N2 C2 120.82(12) no C10 N2 C2 129.48(13) no N4 N3 N2 108.75(12) no N3 N4 C11 109.08(13) no C3 O1 H1A 106(2) no N1 C1 C2 116.76(14) no N1 C1 S1 121.94(13) no C2 C1 S1 121.29(12) no C3 C2 N2 115.41(14) no C3 C2 C1 127.03(15) no N2 C2 C1 117.46(13) no O1 C3 C2 123.80(16) no O1 C3 C4 113.34(15) no C2 C3 C4 122.86(15) no C9 C4 C5 118.73(19) no C9 C4 C3 120.64(16) no C5 C4 C3 120.59(18) no C4 C5 C6 119.5(2) no C4 C5 H5 120.3 no C6 C5 H5 120.3 no C7 C6 C5 120.6(2) no C7 C6 H6 119.7 no C5 C6 H6 119.7 no C8 C7 C6 119.9(2) no C8 C7 H7 120.1 no C6 C7 H7 120.1 no C7 C8 C9 120.3(2) no C7 C8 H8 119.9 no C9 C8 H8 119.9 no C8 C9 C4 121.0(2) no C8 C9 H9 119.5 no C4 C9 H9 119.5 no N2 C10 C15 133.46(16) no N2 C10 C11 104.44(13) no C15 C10 C11 122.10(15) no N4 C11 C10 108.11(14) no N4 C11 C12 130.69(16) no C10 C11 C12 121.18(16) no C13 C12 C11 116.72(18) no C13 C12 H12 121.6 no C11 C12 H12 121.6 no C12 C13 C14 121.58(18) no C12 C13 H13 119.2 no C14 C13 H13 119.2 no C15 C14 C13 122.85(19) no C15 C14 H14 118.6 no C13 C14 H14 118.6 no C14 C15 C10 115.55(19) no C14 C15 H15 122.2 no C10 C15 H15 122.2 no C21 C16 C17 119.74(16) no C21 C16 N1 119.06(14) no C17 C16 N1 120.96(16) no C16 C17 C18 119.4(2) no C16 C17 H17 120.3 no C18 C17 H17 120.3 no C19 C18 C17 120.8(2) no C19 C18 H18 119.6 no C17 C18 H18 119.6 no C18 C19 C20 119.8(2) no C18 C19 H19 120.1 no C20 C19 H19 120.1 no C19 C20 C21 119.8(2) no C19 C20 H20 120.1 no C21 C20 H20 120.1 no C16 C21 C20 120.38(18) no C16 C21 H21 119.8 no C20 C21 H21 119.8 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 C1 1.6816(17) yes N1 C1 1.324(2) yes N1 C16 1.428(2) yes N1 H1 0.855(9) no N2 N3 1.3609(17) yes N2 C10 1.3684(19) no N2 C2 1.4309(19) yes N3 N4 1.2920(18) yes N4 C11 1.374(2) yes O1 C3 1.328(2) yes O1 H1A 0.877(10) no C1 C2 1.458(2) no C2 C3 1.362(2) no C3 C4 1.483(2) no C4 C9 1.373(3) no C4 C5 1.375(3) no C5 C6 1.387(3) no C5 H5 0.9300 no C6 C7 1.363(3) no C6 H6 0.9300 no C7 C8 1.348(3) no C7 H7 0.9300 no C8 C9 1.371(3) no C8 H8 0.9300 no C9 H9 0.9300 no C10 C15 1.386(2) no C10 C11 1.388(2) no C11 C12 1.390(2) no C12 C13 1.358(3) no C12 H12 0.9300 no C13 C14 1.394(3) no C13 H13 0.9300 no C14 C15 1.365(3) no C14 H14 0.9300 no C15 H15 0.9300 no C16 C21 1.367(2) no C16 C17 1.372(2) no C17 C18 1.378(3) no C17 H17 0.9300 no C18 C19 1.362(3) no C18 H18 0.9300 no C19 C20 1.363(3) no C19 H19 0.9300 no C20 C21 1.381(3) no C20 H20 0.9300 no C21 H21 0.9300 no 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 O1 H1A S1 ? 0.88(2) 2.05(2) 2.8752(17) 156(2) yes N1 H1 N2 ? 0.855(12) 2.343(14) 2.7188(15) 107.0(11) yes N1 H1 N4 2_655 0.855(12) 2.112(12) 2.9051(14) 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 _geom_torsion_publ_flag C10 N2 N3 N4 0.73(15) no C2 N2 N3 N4 177.64(12) no N2 N3 N4 C11 -0.64(16) no C16 N1 C1 C2 -169.74(15) no C16 N1 C1 S1 9.3(2) no N3 N2 C2 C3 -92.39(17) yes C10 N2 C2 C3 83.83(19) no N3 N2 C2 C1 84.17(18) yes C10 N2 C2 C1 -99.61(18) no N1 C1 C2 C3 169.67(16) no S1 C1 C2 C3 -9.4(2) no N1 C1 C2 N2 -6.4(2) no S1 C1 C2 N2 174.49(11) no N2 C2 C3 O1 -176.58(15) no C1 C2 C3 O1 7.2(3) no N2 C2 C3 C4 3.6(2) yes C1 C2 C3 C4 -172.61(16) no O1 C3 C4 C9 -112.3(2) no C2 C3 C4 C9 67.5(2) no O1 C3 C4 C5 65.4(2) no C2 C3 C4 C5 -114.8(2) no C9 C4 C5 C6 -2.6(3) no C3 C4 C5 C6 179.62(19) no C4 C5 C6 C7 1.2(4) no C5 C6 C7 C8 1.3(4) no C6 C7 C8 C9 -2.4(4) no C7 C8 C9 C4 1.0(4) no C5 C4 C9 C8 1.6(3) no C3 C4 C9 C8 179.31(19) no N3 N2 C10 C15 179.39(17) no C2 N2 C10 C15 2.8(3) no N3 N2 C10 C11 -0.51(15) no C2 N2 C10 C11 -177.07(14) no N3 N4 C11 C10 0.32(16) no N3 N4 C11 C12 178.50(15) no N2 C10 C11 N4 0.13(15) no C15 C10 C11 N4 -179.78(14) no N2 C10 C11 C12 -178.26(13) no C15 C10 C11 C12 1.8(2) no N4 C11 C12 C13 -178.90(16) no C10 C11 C12 C13 -0.9(2) no C11 C12 C13 C14 0.0(3) no C12 C13 C14 C15 0.2(3) no C13 C14 C15 C10 0.6(3) no N2 C10 C15 C14 178.50(16) no C11 C10 C15 C14 -1.6(2) no C1 N1 C16 C21 -130.91(18) no C1 N1 C16 C17 54.8(2) yes C21 C16 C17 C18 -0.6(3) no N1 C16 C17 C18 173.67(18) no C16 C17 C18 C19 -0.1(3) no C17 C18 C19 C20 1.1(4) no C18 C19 C20 C21 -1.4(3) no C17 C16 C21 C20 0.3(3) no N1 C16 C21 C20 -174.07(17) no C19 C20 C21 C16 0.7(3) no _cod_database_fobs_code 2205079