#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/26/2012605.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_2012605 loop_ _publ_author_name 'Gallagher, John F.' 'Coleman, Clare M.' 'O'Shea, Donal F.' _publ_section_title ; Ethyl 2-{[2-(3-nitrophenyl)-5-phenyl-1H-imidazol-4-yl]sulfanyl}acetate: synthesis via a microwave-mediated combinatorial chemistry approach ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o139 _journal_page_last o141 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C19 H17 N3 O4 S ' _chemical_formula_sum 'C19 H17 N3 O4 S' _chemical_formula_weight 383.42 _chemical_melting_point 463 _chemical_name_systematic ; Ethyl 2-{[2-(3-nitrophenyl)-5-phenyl-1H-imidazol-4-yl]sulfanyl}acetate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 107.389(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.5606(13) _cell_length_b 12.1254(9) _cell_length_c 14.8196(10) _cell_measurement_reflns_used 70 _cell_measurement_temperature 292.0(10) _cell_measurement_theta_max 15.6 _cell_measurement_theta_min 5.4 _cell_volume 1810.9(3) _computing_cell_refinement 'XSCANS (Siemens, 1994)' _computing_data_collection 'XSCANS (Siemens, 1994)' _computing_data_reduction 'XSCANS (Siemens, 1994)' _computing_molecular_graphics 'PLATON (Spek, 1998)' _computing_publication_material 'SHELXL97 and PREP8 (Ferguson, 1998)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 292.0(10) _diffrn_measured_fraction_theta_full 1.00 _diffrn_measured_fraction_theta_max 1.00 _diffrn_measurement_device 'Bruker-AXS P4' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .016 _diffrn_reflns_av_sigmaI/netI .034 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 4517 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 26.0 _diffrn_reflns_theta_min 2.1 _diffrn_standards_decay_% 'variation 1' _diffrn_standards_interval_count 296 _diffrn_standards_number 4 _exptl_absorpt_coefficient_mu .210 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_correction_T_min 1.00 _exptl_absorpt_correction_type none _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 800 _exptl_crystal_size_max .45 _exptl_crystal_size_mid .35 _exptl_crystal_size_min .18 _refine_diff_density_max .21 _refine_diff_density_min -.18 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 245 _refine_ls_number_reflns 3524 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.032 _refine_ls_R_factor_all .066 _refine_ls_R_factor_gt .042 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0496P)^2^+0.459P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .098 _refine_ls_wR_factor_ref .110 _reflns_number_gt 2569 _reflns_number_total 3524 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1525.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _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 2012605 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol S1 .18564(5) .09268(5) .55909(4) .04748(18) Uani d . 1 . . S O1 .12588(18) -.06314(14) .38695(11) .0589(4) Uani d . 1 . . O O2 .00941(17) .06410(15) .28649(11) .0646(5) Uani d . 1 . . O C11 .0745(2) .11400(19) .44312(15) .0453(5) Uani d . 1 . . C C12 .0764(2) .0267(2) .37148(15) .0443(5) Uani d . 1 . . C C13 -.0079(4) -.0100(3) .20684(18) .0947(11) Uani d . 1 . . C C14 -.0799(5) .0444(4) .1220(2) .1380(18) Uani d . 1 . . C C1 .33841(19) .11568(17) .53746(13) .0357(4) Uani d . 1 . . C N1 .34275(15) .13124(14) .44714(11) .0384(4) Uani d . 1 . . N C2 .47011(19) .14464(16) .45516(13) .0357(4) Uani d . 1 . . C N2 .54564(15) .13775(14) .54627(10) .0389(4) Uani d . 1 . . N C3 .46281(19) .11972(17) .60215(13) .0361(4) Uani d . 1 . . C C21 .52093(19) .16416(16) .37448(13) .0355(4) Uani d . 1 . . C C22 .4301(2) .16912(16) .28463(13) .0374(5) Uani d . 1 . . C C23 .4771(2) .18528(17) .20842(13) .0400(5) Uani d . 1 . . C C24 .6102(2) .19680(19) .21716(15) .0476(5) Uani d . 1 . . C C25 .6989(2) .1928(2) .30645(15) .0509(6) Uani d . 1 . . C C26 .6554(2) .17621(18) .38473(14) .0443(5) Uani d . 1 . . C N23 .38144(19) .18805(16) .11352(12) .0484(5) Uani d . 1 . . N O21 .26298(16) .18710(15) .10629(10) .0619(5) Uani d . 1 . . O O22 .42414(18) .19232(16) .04549(10) .0687(5) Uani d . 1 . . O C31 .5123(2) .11105(16) .70503(13) .0371(4) Uani d . 1 . . C C32 .6466(2) .1199(2) .75322(15) .0522(6) Uani d . 1 . . C C33 .6920(2) .1111(2) .85078(15) .0610(7) Uani d . 1 . . C C34 .6052(3) .0926(2) .90191(15) .0548(6) Uani d . 1 . . C C35 .4727(3) .0844(2) .85609(15) .0562(6) Uani d . 1 . . C C36 .4260(2) .0936(2) .75863(14) .0502(6) Uani d . 1 . . C H11A -.0150 .1192 .4478 .054 Uiso calc R 1 . . H H11B .0954 .1843 .4198 .054 Uiso calc R 1 . . H H13A .0781 -.0329 .2025 .114 Uiso calc R 1 . . H H13B -.0558 -.0753 .2158 .114 Uiso calc R 1 . . H H14A -.1685 .0592 .1235 .207 Uiso calc R 1 . . H H14B -.0830 -.0018 .0688 .207 Uiso calc R 1 . . H H14C -.0366 .1127 .1165 .207 Uiso calc R 1 . . H H2 .6306 .1435 .5663 .047 Uiso calc R 1 . . H H22 .3396 .1617 .2762 .045 Uiso calc R 1 . . H H24 .6390 .2069 .1643 .057 Uiso calc R 1 . . H H25 .7890 .2014 .3143 .061 Uiso calc R 1 . . H H26 .7166 .1731 .4446 .053 Uiso calc R 1 . . H H32 .7069 .1319 .7195 .063 Uiso calc R 1 . . H H33 .7822 .1178 .8819 .073 Uiso calc R 1 . . H H34 .6364 .0857 .9673 .066 Uiso calc R 1 . . H H35 .4134 .0726 .8906 .067 Uiso calc R 1 . . H H36 .3353 .0880 .7284 .060 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 .0363(3) .0709(4) .0383(3) -.0029(3) .0159(2) -.0012(3) O1 .0691(11) .0490(10) .0541(9) .0068(9) .0114(8) .0014(8) O2 .0725(11) .0719(12) .0425(9) .0189(9) .0068(8) .0026(8) C11 .0333(11) .0527(14) .0497(12) .0034(10) .0120(9) .0022(10) C12 .0366(11) .0546(14) .0414(12) -.0014(10) .0110(9) .0036(10) C13 .119(3) .107(3) .0454(15) .024(2) .0050(17) -.0149(16) C14 .173(4) .153(4) .0558(19) .043(3) -.015(2) -.008(2) C1 .0363(10) .0400(11) .0328(9) .0001(9) .0133(8) -.0004(8) N1 .0359(9) .0482(10) .0319(8) -.0008(8) .0110(7) .0020(7) C2 .0351(10) .0419(11) .0299(9) -.0014(9) .0093(8) .0014(8) N2 .0316(8) .0548(11) .0302(8) -.0063(8) .0090(7) .0018(8) C3 .0389(10) .0392(11) .0316(9) -.0030(9) .0126(8) -.0001(8) C21 .0382(10) .0382(11) .0313(10) -.0002(9) .0124(8) .0030(8) C22 .0369(10) .0426(12) .0343(10) .0024(9) .0129(8) .0028(8) C23 .0470(12) .0426(12) .0305(10) .0074(10) .0114(9) .0068(9) C24 .0517(13) .0562(14) .0425(12) .0044(11) .0253(10) .0123(10) C25 .0390(11) .0668(16) .0508(13) -.0020(11) .0193(10) .0096(12) C26 .0399(11) .0567(14) .0348(10) -.0039(10) .0088(9) .0042(10) N23 .0563(12) .0564(12) .0325(9) .0135(9) .0131(8) .0062(8) O21 .0502(10) .0885(14) .0418(9) .0135(9) .0058(7) .0090(8) O22 .0795(12) .0984(14) .0324(8) .0168(11) .0232(8) .0084(9) C31 .0440(11) .0367(11) .0311(9) -.0001(9) .0119(8) .0001(8) C32 .0463(13) .0725(17) .0371(11) -.0034(12) .0114(10) .0023(11) C33 .0527(14) .0831(19) .0393(12) -.0013(13) .0018(10) .0004(12) C34 .0726(17) .0595(15) .0291(10) .0036(13) .0102(11) -.0010(10) C35 .0682(16) .0701(17) .0363(11) -.0018(13) .0247(11) .0007(11) C36 .0473(12) .0700(16) .0357(11) -.0007(12) .0163(9) .0004(11) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 C1 . 1.759(2) yes S1 C11 . 1.787(2) yes O1 C12 . 1.201(3) yes O2 C12 . 1.326(3) yes O2 C13 . 1.451(3) yes N1 C1 . 1.366(2) yes N1 C2 . 1.324(2) yes N2 C2 . 1.350(2) yes N2 C3 . 1.390(2) yes C1 C3 . 1.376(3) yes C2 C21 . 1.469(3) yes C3 C31 . 1.460(3) yes C11 C12 . 1.503(3) yes C13 C14 . 1.422(4) yes C21 C22 . 1.391(3) ? C21 C26 . 1.390(3) ? C22 C23 . 1.377(3) ? C23 C24 . 1.379(3) ? C23 N23 . 1.467(3) ? C24 C25 . 1.375(3) ? C25 C26 . 1.384(3) ? N23 O22 . 1.222(2) ? N23 O21 . 1.223(2) ? C31 C32 . 1.388(3) ? C31 C36 . 1.393(3) ? C32 C33 . 1.385(3) ? C33 C34 . 1.371(3) ? C34 C35 . 1.364(3) ? C35 C36 . 1.384(3) ? N2 H2 . .8600 ? C11 H11A . .9700 ? C11 H11B . .9700 ? C13 H13A . .9700 ? C13 H13B . .9700 ? C14 H14A . .9600 ? C14 H14B . .9600 ? C14 H14C . .9600 ? C22 H22 . .9300 ? C24 H24 . .9300 ? C25 H25 . .9300 ? C26 H26 . .9300 ? C32 H32 . .9300 ? C33 H33 . .9300 ? C34 H34 . .9300 ? C35 H35 . .9300 ? C36 H36 . .9300 ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 1 3 0 4 0 0 0 -6 2 -2 -2 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 S1 C11 100.18(9) yes C12 O2 C13 117.6(2) ? S1 C11 C12 115.70(15) yes O1 C12 O2 124.7(2) ? O1 C12 C11 126.9(2) ? O2 C12 C11 108.31(19) ? O2 C13 C14 109.6(3) ? S1 C1 N1 120.12(14) yes S1 C1 C3 127.98(15) yes N1 C1 C3 111.90(17) yes C1 N1 C2 105.05(16) yes N1 C2 N2 111.27(16) yes N1 C2 C21 123.72(17) yes N2 C2 C21 125.01(17) yes C2 N2 C3 108.46(15) yes C1 C3 N2 103.31(16) yes C1 C3 C31 133.95(18) yes N2 C3 C31 122.73(17) yes C2 C21 C22 118.09(17) ? C2 C21 C26 122.55(17) ? C22 C21 C26 119.36(18) ? C21 C22 C23 118.45(18) ? C22 C23 C24 123.01(19) ? C22 C23 N23 118.39(19) ? C24 C23 N23 118.59(18) ? C23 C24 C25 117.95(19) ? C24 C25 C26 120.7(2) ? C21 C26 C25 120.51(19) ? O21 N23 O22 123.21(18) ? O21 N23 C23 118.52(17) ? O22 N23 C23 118.26(19) ? C3 C31 C32 121.57(18) ? C3 C31 C36 121.00(18) ? C32 C31 C36 117.44(18) ? C31 C32 C33 120.8(2) ? C32 C33 C34 120.7(2) ? C33 C34 C35 119.5(2) ? C34 C35 C36 120.4(2) ? C35 C36 C31 121.1(2) ? S1 C11 H11A 108.4 ? S1 C11 H11B 108.4 ? C2 N2 H2 125.8 ? C3 N2 H2 125.8 ? O2 C13 H13A 109.7 ? O2 C13 H13B 109.7 ? C12 C11 H11A 108.4 ? C12 C11 H11B 108.4 ? C14 C13 H13A 109.7 ? C14 C13 H13B 109.7 ? C13 C14 H14A 109.5 ? C13 C14 H14B 109.5 ? C13 C14 H14C 109.5 ? H11A C11 H11B 107.4 ? H13A C13 H13B 108.2 ? H14A C14 H14B 109.5 ? H14A C14 H14C 109.5 ? H14B C14 H14C 109.5 ? C21 C22 H22 120.8 ? C23 C22 H22 120.8 ? C23 C24 H24 121.0 ? C25 C24 H24 121.0 ? C24 C25 H25 119.6 ? C26 C25 H25 119.6 ? C21 C26 H26 119.7 ? C25 C26 H26 119.7 ? C31 C32 H32 119.6 ? C33 C32 H32 119.6 ? C32 C33 H33 119.7 ? C34 C33 H33 119.7 ? C33 C34 H34 120.2 ? C35 C34 H34 120.2 ? C34 C35 H35 119.8 ? C36 C35 H35 119.8 ? C31 C36 H36 119.4 ? C35 C36 H36 119.4 ? 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 N2 H2 O21 4_666 .86 2.46 3.058(2) 128 yes N2 H2 O1 3_656 .86 2.64 3.432(3) 153 yes C36 H36 S1 1_555 .93 2.54 3.271(2) 136 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 C1 S1 C11 C12 70.19(18) yes C13 O2 C12 O1 1.6(4) ? C13 O2 C12 C11 -176.5(2) ? S1 C11 C12 O1 13.9(3) ? S1 C11 C12 O2 -168.09(15) yes C12 O2 C13 C14 -179.1(3) ? C11 S1 C1 N1 -6.30(19) yes C11 S1 C1 C3 174.3(2) ? C3 C1 N1 C2 .2(2) ? S1 C1 N1 C2 -179.23(15) ? C1 N1 C2 N2 .2(2) ? C1 N1 C2 C21 -179.90(18) ? N1 C2 N2 C3 -.6(2) ? C21 C2 N2 C3 179.53(19) ? N1 C1 C3 N2 -.6(2) ? S1 C1 C3 N2 178.83(15) ? N1 C1 C3 C31 178.3(2) ? S1 C1 C3 C31 -2.3(4) ? C2 N2 C3 C1 .7(2) ? C2 N2 C3 C31 -178.37(19) ? N1 C2 C21 C26 -178.9(2) ? N2 C2 C21 C26 .9(3) ? N1 C2 C21 C22 .2(3) yes N2 C2 C21 C22 -179.98(19) ? C26 C21 C22 C23 .4(3) ? C2 C21 C22 C23 -178.78(18) ? C21 C22 C23 C24 .0(3) ? C21 C22 C23 N23 178.66(18) ? C22 C23 C24 C25 -.6(3) ? N23 C23 C24 C25 -179.3(2) ? C23 C24 C25 C26 .9(4) ? C24 C25 C26 C21 -.5(4) ? C22 C21 C26 C25 -.1(3) ? C2 C21 C26 C25 179.0(2) ? C22 C23 N23 O22 -173.5(2) ? C24 C23 N23 O22 5.3(3) ? C22 C23 N23 O21 7.3(3) ? C24 C23 N23 O21 -174.0(2) ? C1 C3 C31 C32 -179.1(2) ? N2 C3 C31 C32 -.3(3) ? C1 C3 C31 C36 .9(4) yes N2 C3 C31 C36 179.6(2) ? C36 C31 C32 C33 .3(3) ? C3 C31 C32 C33 -179.8(2) ? C31 C32 C33 C34 .5(4) ? C32 C33 C34 C35 -.9(4) ? C33 C34 C35 C36 .6(4) ? C34 C35 C36 C31 .1(4) ? C32 C31 C36 C35 -.6(3) ? C3 C31 C36 C35 179.5(2) ? _cod_database_fobs_code 2012605