#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/00/2200072.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_2200072 loop_ _publ_author_name 'Lynch, Daniel E.' 'McClenaghan, Ian' _publ_section_title ; 2-Amino-4,6-bis(phenylthio)pyrimidine ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o26 _journal_page_last o27 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C16 H13 N3 S2' _chemical_formula_sum 'C16 H13 N3 S2' _chemical_formula_weight 311.41 _chemical_name_systematic ; 2-Amino-4,6-bis(phenylthio)pyrimidine ; _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' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 95.73(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.7937(18) _cell_length_b 8.3091(17) _cell_length_c 21.148(4) _cell_measurement_reflns_used 6016 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 1.00 _cell_volume 1537.5(5) _computing_cell_refinement 'DENZO and COLLECT' _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO and COLLECT' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 9.091 _diffrn_measured_fraction_theta_full .984 _diffrn_measured_fraction_theta_max .984 _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .088 _diffrn_reflns_av_sigmaI/netI .0778 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 12370 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 1.94 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .342 _exptl_absorpt_correction_T_max .947 _exptl_absorpt_correction_T_min .893 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 648 _exptl_crystal_size_max .34 _exptl_crystal_size_mid .18 _exptl_crystal_size_min .16 _refine_diff_density_max .292 _refine_diff_density_min -.467 _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 198 _refine_ls_number_reflns 3476 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.004 _refine_ls_R_factor_all .077 _refine_ls_R_factor_gt .046 _refine_ls_shift/su_max .009 _refine_ls_shift/su_mean .001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0595P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .117 _reflns_number_gt 2440 _reflns_number_total 3476 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ob6001.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: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' 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 2200072 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 N1 -.11796(16) .86840(19) .05032(7) .0250(4) Uani d . 1 . . N C2 -.2636(2) .9113(2) .03158(9) .0263(4) Uani d . 1 . . C N21 -.2840(2) 1.0482(2) -.00121(9) .0377(5) Uani d . 1 . . N H21 -.367(3) 1.078(3) -.0130(11) .046(7) Uiso d . 1 . . H H22 -.195(2) 1.096(3) -.0085(10) .045(7) Uiso d . 1 . . H N3 -.38907(16) .82762(19) .04364(7) .0277(4) Uani d . 1 . . N C4 -.3641(2) .6896(2) .07527(8) .0243(4) Uani d . 1 . . C C5 -.21929(18) .6316(2) .09563(8) .0225(4) Uani d . 1 . . C H5 -.2033 .5322 .1175 .028 Uiso calc R 1 . . H C6 -.09983(19) .7301(2) .08166(8) .0219(4) Uani d . 1 . . C S1 -.53545(5) .59059(7) .08775(3) .0405(2) Uani d . 1 . . S C7 -.47507(19) .4307(2) .13952(9) .0263(4) Uani d . 1 . . C C8 -.4799(2) .2752(3) .11697(11) .0407(5) Uani d . 1 . . C H8 -.5110 .2544 .0734 .051 Uiso calc R 1 . . H C9 -.4391(3) .1490(3) .15819(13) .0524(7) Uani d . 1 . . C H9 -.4433 .0414 .1429 .065 Uiso calc R 1 . . H C10 -.3931(2) .1792(3) .22057(12) .0480(6) Uani d . 1 . . C H10 -.3642 .0924 .2485 .060 Uiso calc R 1 . . H C11 -.3881(3) .3333(3) .24326(11) .0451(6) Uani d . 1 . . C H11 -.3552 .3535 .2867 .056 Uiso calc R 1 . . H C12 -.4314(2) .4599(3) .20276(10) .0364(5) Uani d . 1 . . C H12 -.4308 .5668 .2187 .045 Uiso calc R 1 . . H S2 .09499(5) .69097(6) .10351(2) .02865(17) Uani d . 1 . . S C13 .09830(18) .4884(2) .13030(9) .0230(4) Uani d . 1 . . C C14 .0717(2) .3629(3) .08753(9) .0302(5) Uani d . 1 . . C H14 .0485 .3850 .0435 .038 Uiso calc R 1 . . H C15 .0789(2) .2053(3) .10885(10) .0343(5) Uani d . 1 . . C H15 .0593 .1190 .0797 .043 Uiso calc R 1 . . H C16 .1147(2) .1744(3) .17267(10) .0357(5) Uani d . 1 . . C H16 .1203 .0663 .1874 .045 Uiso calc R 1 . . H C17 .1425(2) .2983(3) .21503(10) .0387(5) Uani d . 1 . . C H17 .1675 .2757 .2589 .048 Uiso calc R 1 . . H C18 .1342(2) .4560(3) .19428(9) .0299(5) Uani d . 1 . . C H18 .1530 .5417 .2237 .037 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 N1 .0262(8) .0199(9) .0286(9) .0012(6) .0017(6) .0019(7) C2 .0319(11) .0210(11) .0263(10) .0065(8) .0036(8) .0042(8) N21 .0350(11) .0288(11) .0489(12) .0064(9) .0029(9) .0172(9) N3 .0240(8) .0269(10) .0324(9) .0066(7) .0033(7) .0086(7) C4 .0236(10) .0251(11) .0243(10) .0030(7) .0037(7) .0049(8) C5 .0210(9) .0213(10) .0251(10) .0032(7) .0013(7) .0056(8) C6 .0219(9) .0222(11) .0216(10) .0049(7) .0023(7) .0000(8) S1 .0180(3) .0464(4) .0569(4) .0036(2) .0030(2) .0258(3) C7 .0178(9) .0294(12) .0322(11) .0019(8) .0045(7) .0087(9) C8 .0431(13) .0414(15) .0374(13) .0001(10) .0024(9) -.0034(11) C9 .0602(16) .0285(14) .0694(19) .0039(11) .0112(13) .0011(13) C10 .0408(13) .0454(17) .0579(17) .0075(11) .0060(11) .0268(13) C11 .0425(13) .0588(18) .0339(13) -.0049(11) .0036(10) .0152(12) C12 .0378(12) .0355(14) .0370(13) -.0040(9) .0098(9) -.0010(10) S2 .0187(3) .0248(3) .0419(3) -.00065(18) .0004(2) .0068(2) C13 .0147(9) .0228(11) .0313(11) .0011(7) .0020(7) .0023(8) C14 .0315(11) .0301(12) .0284(11) .0042(8) .0006(8) -.0002(9) C15 .0369(12) .0275(12) .0376(13) .0029(9) -.0002(9) -.0059(10) C16 .0408(12) .0241(13) .0418(13) .0027(9) .0027(9) .0068(10) C17 .0509(14) .0362(14) .0277(12) .0051(10) -.0016(9) .0077(10) C18 .0294(10) .0275(12) .0317(12) .0033(8) -.0025(8) -.0029(9) 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 N1 C6 . 1.328(2) ? N1 C2 . 1.350(2) ? C2 N21 . 1.335(3) ? C2 N3 . 1.350(2) ? N21 H21 . .78(2) ? N21 H22 . .90(2) ? N3 C4 . 1.335(2) ? C4 C5 . 1.389(2) ? C4 S1 . 1.7593(18) ? C5 C6 . 1.387(2) ? C5 H5 . .9500 ? C6 S2 . 1.7596(18) ? S1 C7 . 1.7693(19) ? C7 C8 . 1.376(3) ? C7 C12 . 1.376(3) ? C8 C9 . 1.388(3) ? C8 H8 . .9500 ? C9 C10 . 1.364(3) ? C9 H9 . .9500 ? C10 C11 . 1.366(3) ? C10 H10 . .9500 ? C11 C12 . 1.386(3) ? C11 H11 . .9500 ? C12 H12 . .9500 ? S2 C13 . 1.775(2) ? C13 C14 . 1.385(3) ? C13 C18 . 1.385(3) ? C14 C15 . 1.384(3) ? C14 H14 . .9500 ? C15 C16 . 1.379(3) ? C15 H15 . .9500 ? C16 C17 . 1.371(3) ? C16 H16 . .9500 ? C17 C18 . 1.381(3) ? C17 H17 . .9500 ? C18 H18 . .9500 ? 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' S S .1246 .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 C6 N1 C2 115.99(15) N21 C2 N3 117.86(18) N21 C2 N1 116.86(18) N3 C2 N1 125.28(17) C2 N21 H21 120.3(18) C2 N21 H22 113.2(15) H21 N21 H22 127(2) C4 N3 C2 116.17(15) N3 C4 C5 123.56(16) N3 C4 S1 112.12(13) C5 C4 S1 124.32(14) C6 C5 C4 114.83(17) C6 C5 H5 122.6 C4 C5 H5 122.6 N1 C6 C5 124.14(16) N1 C6 S2 110.87(13) C5 C6 S2 124.99(14) C4 S1 C7 103.61(9) C8 C7 C12 119.90(19) C8 C7 S1 119.57(16) C12 C7 S1 120.43(16) C7 C8 C9 119.6(2) C7 C8 H8 120.2 C9 C8 H8 120.2 C10 C9 C8 120.1(2) C10 C9 H9 119.9 C8 C9 H9 119.9 C9 C10 C11 120.5(2) C9 C10 H10 119.7 C11 C10 H10 119.7 C10 C11 C12 119.8(2) C10 C11 H11 120.1 C12 C11 H11 120.1 C7 C12 C11 120.0(2) C7 C12 H12 120.0 C11 C12 H12 120.0 C6 S2 C13 104.10(8) C14 C13 C18 119.90(18) C14 C13 S2 120.60(15) C18 C13 S2 119.44(15) C15 C14 C13 120.02(19) C15 C14 H14 120.0 C13 C14 H14 120.0 C16 C15 C14 119.6(2) C16 C15 H15 120.2 C14 C15 H15 120.2 C17 C16 C15 120.5(2) C17 C16 H16 119.7 C15 C16 H16 119.7 C16 C17 C18 120.3(2) C16 C17 H17 119.8 C18 C17 H17 119.8 C17 C18 C13 119.67(19) C17 C18 H18 120.2 C13 C18 H18 120.2 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 N21 H21 N3 3_475 .78(2) 2.32(2) 3.102(2) 177(2) yes N21 H22 S2 3_575 .90(2) 2.88(2) 3.586(2) 136.2(17) 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 C6 N1 C2 N21 -178.56(18) C6 N1 C2 N3 1.8(3) N21 C2 N3 C4 178.52(18) N1 C2 N3 C4 -1.8(3) C2 N3 C4 C5 .3(3) C2 N3 C4 S1 -179.60(14) N3 C4 C5 C6 1.1(3) S1 C4 C5 C6 -179.02(14) C2 N1 C6 C5 -.2(3) C2 N1 C6 S2 -179.51(13) C4 C5 C6 N1 -1.2(3) C4 C5 C6 S2 178.06(14) N3 C4 S1 C7 -171.71(14) C5 C4 S1 C7 8.43(19) C4 S1 C7 C8 -108.49(16) C4 S1 C7 C12 75.05(17) C12 C7 C8 C9 -.6(3) S1 C7 C8 C9 -177.11(16) C7 C8 C9 C10 -.6(3) C8 C9 C10 C11 .7(4) C9 C10 C11 C12 .5(3) C8 C7 C12 C11 1.8(3) S1 C7 C12 C11 178.29(16) C10 C11 C12 C7 -1.8(3) N1 C6 S2 C13 -169.17(13) C5 C6 S2 C13 11.49(18) C6 S2 C13 C14 72.38(16) C6 S2 C13 C18 -110.35(15) C18 C13 C14 C15 .9(3) S2 C13 C14 C15 178.16(14) C13 C14 C15 C16 -.9(3) C14 C15 C16 C17 .3(3) C15 C16 C17 C18 .3(3) C16 C17 C18 C13 -.3(3) C14 C13 C18 C17 -.3(3) S2 C13 C18 C17 -177.61(15)