# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Deepak Chopra' _publ_contact_author_email DCHOPRA@IISERBHOPAL.AC.IN _publ_section_title ; Effect of substitution on molecular conformation and packing features in a series of aryl substituted ethyl-6-methyl-4-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates. ; loop_ _publ_author_name 'Deepak Chopra' 'Tayur Guru Row' 'Susanta K Nayak' Vasu 'K. N. Venugopala' # Attachment 'PYR6.txt' # CIF-file generated for PYR6 in C2/c #============================================================================== data_s4ocm _database_code_depnum_ccdc_archive 'CCDC 732834' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 4-(4-Methoxy-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5- carboxylic acid ethyl ester ; _chemical_name_common ; 4-(4-Methoxy-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro- pyrimidine-5-carboxylic acid ethyl ester ; _chemical_melting_point ? _chemical_formula_moiety 'C15 H18 N2 O3 S' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C15 H18 N2 O3 S' _chemical_formula_iupac ? _chemical_formula_weight 306.38 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' N N 0.0061 0.0033 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 2/c' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,y,1/2-z 3 -x,-y,-z 4 x,-y,1/2+z 5 1/2+x,1/2+y,z 6 1/2-x,1/2+y,1/2-z 7 1/2-x,1/2-y,-z 8 1/2+x,1/2-y,1/2+z _cell_length_a 18.239(2) _cell_length_b 7.3435(8) _cell_length_c 25.197(3) _cell_angle_alpha 90 _cell_angle_beta 101.957(3) _cell_angle_gamma 90 _cell_volume 3301.7(6) _cell_formula_units_Z 8 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 340 _cell_measurement_theta_min 27.98 _cell_measurement_theta_max 0.91 _cell_special_details ; ; _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.21 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 0.207 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9018 _exptl_absorpt_correction_T_max 0.9579 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 15282 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0138 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 25.00 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2907 # number of observed reflections (> n sig(I)) _reflns_number_gt 2549 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0820P)^2^+2.8590P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2907 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0525 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1418 _refine_ls_wR_factor_gt 0.1376 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.385 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.051 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.19392(3) 0.50113(7) 0.51764(2) 0.0486(2) Uani 1 1 d . . . O3 O 0.35869(10) 1.0553(3) 0.76093(7) 0.0624(5) Uani 1 1 d . . . O2 O -0.04325(10) 1.0674(2) 0.60406(8) 0.0622(5) Uani 1 1 d . . . O1 O 0.03178(10) 1.2652(2) 0.57497(8) 0.0581(5) Uani 1 1 d . . . N1 N 0.08502(9) 0.6420(2) 0.55941(7) 0.0384(4) Uani 1 1 d . . . H1N H 0.0752 0.5308 0.5661 0.046 Uiso 1 1 calc R . . N2 N 0.16495(10) 0.8487(2) 0.53512(7) 0.0388(4) Uani 1 1 d . . . H2N H 0.1938 0.8774 0.5134 0.047 Uiso 1 1 calc R . . C1 C 0.14701(11) 0.6753(3) 0.53858(7) 0.0355(4) Uani 1 1 d . . . C9 C 0.19287(11) 1.0200(2) 0.62023(8) 0.0357(4) Uani 1 1 d . . . C4 C 0.13832(11) 0.9959(2) 0.56628(8) 0.0354(4) Uani 1 1 d . . . H4 H 0.1371 1.1093 0.5456 0.042 Uiso 1 1 calc R . . C3 C 0.05938(11) 0.9518(3) 0.57201(8) 0.0353(4) Uani 1 1 d . . . C2 C 0.03668(11) 0.7765(3) 0.57050(8) 0.0359(4) Uani 1 1 d . . . C12 C 0.30141(13) 1.0410(3) 0.71645(9) 0.0458(5) Uani 1 1 d . . . C13 C 0.23520(14) 0.9488(3) 0.71541(9) 0.0492(6) Uani 1 1 d . . . H13 H 0.2263 0.8939 0.7467 0.059 Uiso 1 1 calc R . . C5 C 0.01509(12) 1.1102(3) 0.58301(9) 0.0403(5) Uani 1 1 d . . . C14 C 0.18230(12) 0.9386(3) 0.66772(8) 0.0430(5) Uani 1 1 d . . . H14 H 0.1381 0.8750 0.6674 0.052 Uiso 1 1 calc R . . C8 C -0.03626(12) 0.7013(3) 0.57876(11) 0.0538(6) Uani 1 1 d . . . H8A H -0.0351 0.6908 0.6169 0.081 Uiso 1 1 calc R . . H8B H -0.0443 0.5834 0.5622 0.081 Uiso 1 1 calc R . . H8C H -0.0762 0.7815 0.5625 0.081 Uiso 1 1 calc R . . C10 C 0.25893(12) 1.1170(3) 0.62256(9) 0.0436(5) Uani 1 1 d . . . H10 H 0.2670 1.1761 0.5916 0.052 Uiso 1 1 calc R . . C11 C 0.31256(12) 1.1271(3) 0.66967(9) 0.0477(5) Uani 1 1 d . . . H11 H 0.3565 1.1919 0.6702 0.057 Uiso 1 1 calc R . . C6 C -0.08944(15) 1.2149(3) 0.61751(12) 0.0622(7) Uani 1 1 d . . . H6A H -0.1143 1.2776 0.5848 0.075 Uiso 1 1 calc R . . H6B H -0.0588 1.3020 0.6412 0.075 Uiso 1 1 calc R . . C15 C 0.3522(2) 0.9521(5) 0.80787(12) 0.0881(10) Uani 1 1 d . . . H15A H 0.3120 1.0001 0.8229 0.132 Uiso 1 1 calc R . . H15B H 0.3983 0.9598 0.8344 0.132 Uiso 1 1 calc R . . H15C H 0.3420 0.8271 0.7978 0.132 Uiso 1 1 calc R . . C7 C -0.1452(2) 1.1331(5) 0.64499(19) 0.1024(13) Uani 1 1 d . . . H7A H -0.1721 1.0393 0.6225 0.154 Uiso 1 1 calc R . . H7B H -0.1797 1.2252 0.6515 0.154 Uiso 1 1 calc R . . H7C H -0.1202 1.0816 0.6790 0.154 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0536(4) 0.0329(3) 0.0668(4) -0.0067(2) 0.0298(3) -0.0032(2) O3 0.0657(11) 0.0590(10) 0.0553(10) -0.0010(8) -0.0037(8) -0.0056(9) O2 0.0609(10) 0.0316(8) 0.1078(14) 0.0035(8) 0.0494(10) 0.0041(7) O1 0.0614(10) 0.0251(8) 0.0958(13) 0.0008(8) 0.0347(9) -0.0025(7) N1 0.0438(9) 0.0244(8) 0.0514(10) 0.0017(7) 0.0202(8) -0.0048(7) N2 0.0483(10) 0.0314(9) 0.0426(9) -0.0043(7) 0.0234(8) -0.0080(7) C1 0.0390(10) 0.0346(10) 0.0339(9) -0.0014(8) 0.0101(8) -0.0040(8) C9 0.0406(10) 0.0252(9) 0.0442(11) -0.0025(8) 0.0157(9) -0.0011(8) C4 0.0418(11) 0.0253(9) 0.0421(11) 0.0002(7) 0.0159(9) -0.0030(8) C3 0.0378(10) 0.0278(10) 0.0416(10) 0.0006(8) 0.0108(8) -0.0029(8) C2 0.0367(10) 0.0305(10) 0.0416(10) 0.0009(8) 0.0106(8) -0.0027(8) C12 0.0518(13) 0.0349(11) 0.0488(12) -0.0062(9) 0.0061(10) 0.0018(9) C13 0.0622(14) 0.0427(12) 0.0448(12) 0.0050(10) 0.0159(11) -0.0045(11) C5 0.0421(11) 0.0314(11) 0.0490(11) 0.0014(8) 0.0131(9) -0.0006(8) C14 0.0478(12) 0.0368(11) 0.0471(12) 0.0019(9) 0.0159(10) -0.0090(9) C8 0.0423(12) 0.0363(12) 0.0882(17) -0.0047(11) 0.0257(12) -0.0082(9) C10 0.0501(12) 0.0373(11) 0.0470(11) 0.0009(9) 0.0185(10) -0.0081(9) C11 0.0429(11) 0.0441(12) 0.0571(13) -0.0041(10) 0.0127(10) -0.0114(9) C6 0.0614(15) 0.0387(13) 0.0948(19) 0.0006(12) 0.0357(14) 0.0104(11) C15 0.118(3) 0.0712(19) 0.0594(17) 0.0126(15) -0.0189(17) -0.0118(19) C7 0.100(3) 0.0619(19) 0.168(4) -0.008(2) 0.080(3) 0.0035(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.683(2) . ? O3 C12 1.369(3) . ? O3 C15 1.430(3) . ? O2 C5 1.321(3) . ? O2 C6 1.455(3) . ? O1 C5 1.206(2) . ? N1 C1 1.363(2) . ? N1 C2 1.390(2) . ? N1 H1N 0.8600 . ? N2 C1 1.322(3) . ? N2 C4 1.476(2) . ? N2 H2N 0.8600 . ? C9 C14 1.386(3) . ? C9 C10 1.390(3) . ? C9 C4 1.519(3) . ? C4 C3 1.512(3) . ? C4 H4 0.9800 . ? C3 C2 1.351(3) . ? C3 C5 1.474(3) . ? C2 C8 1.494(3) . ? C12 C13 1.380(3) . ? C12 C11 1.389(3) . ? C13 C14 1.379(3) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C10 C11 1.375(3) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C6 C7 1.472(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 O3 C15 117.2(2) . . ? C5 O2 C6 118.04(18) . . ? C1 N1 C2 124.12(16) . . ? C1 N1 H1N 117.9 . . ? C2 N1 H1N 117.9 . . ? C1 N2 C4 123.85(16) . . ? C1 N2 H2N 118.1 . . ? C4 N2 H2N 118.1 . . ? N2 C1 N1 115.75(17) . . ? N2 C1 S1 124.21(15) . . ? N1 C1 S1 120.02(15) . . ? C14 C9 C10 117.30(19) . . ? C14 C9 C4 122.65(18) . . ? C10 C9 C4 119.90(17) . . ? N2 C4 C3 108.60(15) . . ? N2 C4 C9 109.56(16) . . ? C3 C4 C9 113.55(16) . . ? N2 C4 H4 108.3 . . ? C3 C4 H4 108.3 . . ? C9 C4 H4 108.3 . . ? C2 C3 C5 125.48(18) . . ? C2 C3 C4 119.59(18) . . ? C5 C3 C4 114.78(16) . . ? C3 C2 N1 118.65(17) . . ? C3 C2 C8 128.67(19) . . ? N1 C2 C8 112.68(17) . . ? O3 C12 C13 124.7(2) . . ? O3 C12 C11 116.0(2) . . ? C13 C12 C11 119.2(2) . . ? C14 C13 C12 119.7(2) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? O1 C5 O2 122.95(19) . . ? O1 C5 C3 123.06(19) . . ? O2 C5 C3 113.96(17) . . ? C13 C14 C9 122.1(2) . . ? C13 C14 H14 118.9 . . ? C9 C14 H14 118.9 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C11 C10 C9 121.30(19) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C12 120.3(2) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? O2 C6 C7 107.2(2) . . ? O2 C6 H6A 110.3 . . ? C7 C6 H6A 110.3 . . ? O2 C6 H6B 110.3 . . ? C7 C6 H6B 110.3 . . ? H6A C6 H6B 108.5 . . ? O3 C15 H15A 109.5 . . ? O3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N2 C1 N1 19.4(3) . . . . ? C4 N2 C1 S1 -162.39(15) . . . . ? C2 N1 C1 N2 7.9(3) . . . . ? C2 N1 C1 S1 -170.43(15) . . . . ? C1 N2 C4 C3 -35.1(3) . . . . ? C1 N2 C4 C9 89.4(2) . . . . ? C14 C9 C4 N2 -96.0(2) . . . . ? C10 C9 C4 N2 79.6(2) . . . . ? C14 C9 C4 C3 25.6(3) . . . . ? C10 C9 C4 C3 -158.77(18) . . . . ? N2 C4 C3 C2 26.4(3) . . . . ? C9 C4 C3 C2 -95.7(2) . . . . ? N2 C4 C3 C5 -157.88(17) . . . . ? C9 C4 C3 C5 80.0(2) . . . . ? C5 C3 C2 N1 179.82(18) . . . . ? C4 C3 C2 N1 -5.0(3) . . . . ? C5 C3 C2 C8 0.6(4) . . . . ? C4 C3 C2 C8 175.7(2) . . . . ? C1 N1 C2 C3 -14.7(3) . . . . ? C1 N1 C2 C8 164.69(19) . . . . ? C15 O3 C12 C13 6.5(4) . . . . ? C15 O3 C12 C11 -173.5(2) . . . . ? O3 C12 C13 C14 -178.0(2) . . . . ? C11 C12 C13 C14 2.1(3) . . . . ? C6 O2 C5 O1 0.6(4) . . . . ? C6 O2 C5 C3 178.6(2) . . . . ? C2 C3 C5 O1 -166.9(2) . . . . ? C4 C3 C5 O1 17.7(3) . . . . ? C2 C3 C5 O2 15.1(3) . . . . ? C4 C3 C5 O2 -160.31(19) . . . . ? C12 C13 C14 C9 -0.7(4) . . . . ? C10 C9 C14 C13 -1.3(3) . . . . ? C4 C9 C14 C13 174.4(2) . . . . ? C14 C9 C10 C11 1.9(3) . . . . ? C4 C9 C10 C11 -173.95(19) . . . . ? C9 C10 C11 C12 -0.5(3) . . . . ? O3 C12 C11 C10 178.5(2) . . . . ? C13 C12 C11 C10 -1.5(3) . . . . ? C5 O2 C6 C7 -174.4(3) . . . . ? # CIF-file generated for PYR1 in P-1 #============================================================================== data_s4f_m _database_code_depnum_ccdc_archive 'CCDC 732835' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 4-(4-Fluoro-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester ; _chemical_name_common ; 4-(4-Fluoro-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro- pyrimidine-5-carboxylic ; _chemical_melting_point ? _chemical_formula_moiety 'C14 H15 F N2 O2 S' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C14 H15 F N2 O2 S' _chemical_formula_iupac ? _chemical_formula_weight 294.35 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' N N 0.0061 0.0033 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 7.347(2) _cell_length_b 9.542(3) _cell_length_c 11.327(4) _cell_angle_alpha 71.093(5) _cell_angle_beta 88.642(5) _cell_angle_gamma 69.792(5) _cell_volume 701.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 400 _cell_measurement_theta_min 27.99 _cell_measurement_theta_max 0.91 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.245 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9072 _exptl_absorpt_correction_T_max 0.9481 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 7222 _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 25.99 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2723 # number of observed reflections (> n sig(I)) _reflns_number_gt 2400 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0608P)^2^+0.2951P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2723 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1156 _refine_ls_wR_factor_gt 0.1121 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.290 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.050 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.20133(7) 0.09201(6) 0.55149(5) 0.04446(18) Uani 1 1 d . . . N2 N 0.5177(2) 0.15417(18) 0.58685(14) 0.0364(3) Uani 1 1 d . . . H2N H 0.5715 0.1007 0.5391 0.044 Uiso 1 1 calc R . . O1 O 0.79002(18) 0.44542(16) 0.64420(13) 0.0432(3) Uani 1 1 d . . . N1 N 0.2391(2) 0.30078(18) 0.64675(14) 0.0364(3) Uani 1 1 d . . . H1N H 0.1227 0.3122 0.6674 0.044 Uiso 1 1 calc R . . O2 O 0.54505(19) 0.55288(17) 0.74572(15) 0.0496(4) Uani 1 1 d . . . C3 C 0.5192(2) 0.3624(2) 0.66499(16) 0.0317(4) Uani 1 1 d . . . C1 C 0.3285(2) 0.1849(2) 0.59793(16) 0.0331(4) Uani 1 1 d . . . F1 F 1.0007(2) -0.28654(18) 1.10285(13) 0.0771(5) Uani 1 1 d . . . C9 C 0.7383(2) 0.0761(2) 0.77547(16) 0.0322(4) Uani 1 1 d . . . C2 C 0.3246(2) 0.4026(2) 0.66551(16) 0.0329(4) Uani 1 1 d . . . C4 C 0.6408(2) 0.2059(2) 0.65120(16) 0.0319(4) Uani 1 1 d . . . H4 H 0.7435 0.2229 0.5979 0.038 Uiso 1 1 calc R . . C14 C 0.6799(3) 0.0866(2) 0.89023(18) 0.0415(4) Uani 1 1 d . . . H14 H 0.5797 0.1771 0.8929 0.050 Uiso 1 1 calc R . . C5 C 0.6318(2) 0.4573(2) 0.68148(16) 0.0335(4) Uani 1 1 d . . . C10 C 0.8895(3) -0.0598(2) 0.77383(18) 0.0414(4) Uani 1 1 d . . . H10 H 0.9317 -0.0683 0.6975 0.050 Uiso 1 1 calc R . . C6 C 0.6435(3) 0.6509(3) 0.7689(2) 0.0490(5) Uani 1 1 d . . . H6A H 0.6504 0.7294 0.6908 0.059 Uiso 1 1 calc R . . H6B H 0.7750 0.5862 0.8078 0.059 Uiso 1 1 calc R . . C8 C 0.1793(3) 0.5487(2) 0.6808(2) 0.0470(5) Uani 1 1 d . . . H8A H 0.1475 0.5259 0.7660 0.071 Uiso 1 1 calc R . . H8B H 0.0635 0.5834 0.6256 0.071 Uiso 1 1 calc R . . H8C H 0.2337 0.6308 0.6606 0.071 Uiso 1 1 calc R . . C13 C 0.7680(3) -0.0353(3) 1.00160(19) 0.0491(5) Uani 1 1 d . . . H13 H 0.7284 -0.0276 1.0785 0.059 Uiso 1 1 calc R . . C12 C 0.9141(3) -0.1664(2) 0.99489(19) 0.0478(5) Uani 1 1 d . . . C11 C 0.9777(3) -0.1821(2) 0.8834(2) 0.0495(5) Uani 1 1 d . . . H11 H 1.0780 -0.2731 0.8818 0.059 Uiso 1 1 calc R . . C7 C 0.5292(4) 0.7293(4) 0.8532(3) 0.0781(9) Uani 1 1 d . . . H7A H 0.3979 0.7891 0.8153 0.117 Uiso 1 1 calc R . . H7B H 0.5867 0.7994 0.8678 0.117 Uiso 1 1 calc R . . H7C H 0.5286 0.6507 0.9316 0.117 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0333(3) 0.0507(3) 0.0625(3) -0.0335(3) 0.0072(2) -0.0174(2) N2 0.0261(7) 0.0447(8) 0.0444(8) -0.0271(7) 0.0039(6) -0.0086(6) O1 0.0293(7) 0.0540(8) 0.0551(8) -0.0261(7) 0.0101(5) -0.0185(6) N1 0.0258(7) 0.0440(8) 0.0493(9) -0.0265(7) 0.0117(6) -0.0148(6) O2 0.0370(7) 0.0568(8) 0.0778(10) -0.0445(8) 0.0188(7) -0.0245(6) C3 0.0267(8) 0.0332(9) 0.0363(9) -0.0139(7) 0.0038(6) -0.0100(7) C1 0.0298(9) 0.0358(9) 0.0342(8) -0.0139(7) 0.0031(6) -0.0102(7) F1 0.0782(10) 0.0639(9) 0.0563(8) 0.0035(7) -0.0102(7) -0.0069(8) C9 0.0236(8) 0.0359(9) 0.0409(9) -0.0167(7) 0.0037(6) -0.0116(7) C2 0.0289(8) 0.0343(9) 0.0381(9) -0.0162(7) 0.0053(7) -0.0108(7) C4 0.0243(8) 0.0372(9) 0.0385(9) -0.0180(7) 0.0060(6) -0.0114(7) C14 0.0373(10) 0.0413(10) 0.0446(10) -0.0191(8) 0.0061(8) -0.0084(8) C5 0.0293(8) 0.0328(9) 0.0366(9) -0.0109(7) 0.0011(7) -0.0094(7) C10 0.0313(9) 0.0455(10) 0.0468(10) -0.0196(9) 0.0071(7) -0.0094(8) C6 0.0432(11) 0.0514(12) 0.0703(14) -0.0337(11) 0.0128(10) -0.0264(9) C8 0.0280(9) 0.0446(11) 0.0743(14) -0.0325(10) 0.0076(9) -0.0085(8) C13 0.0527(12) 0.0546(12) 0.0390(10) -0.0162(9) 0.0054(8) -0.0176(10) C12 0.0419(11) 0.0454(11) 0.0476(11) -0.0061(9) -0.0058(8) -0.0138(9) C11 0.0333(10) 0.0416(11) 0.0628(13) -0.0154(9) 0.0011(9) -0.0023(8) C7 0.0679(16) 0.096(2) 0.118(2) -0.0778(19) 0.0370(16) -0.0491(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.6835(18) . ? N2 C1 1.330(2) . ? N2 C4 1.471(2) . ? N2 H2N 0.8600 . ? O1 C5 1.208(2) . ? N1 C1 1.355(2) . ? N1 C2 1.395(2) . ? N1 H1N 0.8600 . ? O2 C5 1.332(2) . ? O2 C6 1.451(2) . ? C3 C2 1.346(2) . ? C3 C5 1.475(2) . ? C3 C4 1.509(2) . ? F1 C12 1.356(2) . ? C9 C14 1.383(3) . ? C9 C10 1.392(2) . ? C9 C4 1.527(2) . ? C2 C8 1.495(2) . ? C4 H4 0.9800 . ? C14 C13 1.390(3) . ? C14 H14 0.9300 . ? C10 C11 1.378(3) . ? C10 H10 0.9300 . ? C6 C7 1.472(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C13 C12 1.361(3) . ? C13 H13 0.9300 . ? C12 C11 1.372(3) . ? C11 H11 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N2 C4 124.14(14) . . ? C1 N2 H2N 117.9 . . ? C4 N2 H2N 117.9 . . ? C1 N1 C2 123.84(14) . . ? C1 N1 H1N 118.1 . . ? C2 N1 H1N 118.1 . . ? C5 O2 C6 118.17(14) . . ? C2 C3 C5 125.52(15) . . ? C2 C3 C4 119.88(15) . . ? C5 C3 C4 114.57(14) . . ? N2 C1 N1 115.91(15) . . ? N2 C1 S1 123.39(13) . . ? N1 C1 S1 120.67(13) . . ? C14 C9 C10 118.32(17) . . ? C14 C9 C4 122.62(15) . . ? C10 C9 C4 119.05(15) . . ? C3 C2 N1 118.63(15) . . ? C3 C2 C8 128.39(16) . . ? N1 C2 C8 112.95(15) . . ? N2 C4 C3 108.99(13) . . ? N2 C4 C9 110.14(14) . . ? C3 C4 C9 113.70(14) . . ? N2 C4 H4 107.9 . . ? C3 C4 H4 107.9 . . ? C9 C4 H4 107.9 . . ? C9 C14 C13 121.28(18) . . ? C9 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? O1 C5 O2 123.41(16) . . ? O1 C5 C3 123.29(16) . . ? O2 C5 C3 113.25(15) . . ? C11 C10 C9 121.10(18) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? O2 C6 C7 106.98(16) . . ? O2 C6 H6A 110.3 . . ? C7 C6 H6A 110.3 . . ? O2 C6 H6B 110.3 . . ? C7 C6 H6B 110.3 . . ? H6A C6 H6B 108.6 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C12 C13 C14 118.14(19) . . ? C12 C13 H13 120.9 . . ? C14 C13 H13 120.9 . . ? F1 C12 C13 118.7(2) . . ? F1 C12 C11 118.54(19) . . ? C13 C12 C11 122.75(19) . . ? C12 C11 C10 118.41(18) . . ? C12 C11 H11 120.8 . . ? C10 C11 H11 120.8 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N2 C1 N1 16.1(2) . . . . ? C4 N2 C1 S1 -165.59(13) . . . . ? C2 N1 C1 N2 10.7(3) . . . . ? C2 N1 C1 S1 -167.63(13) . . . . ? C5 C3 C2 N1 179.05(15) . . . . ? C4 C3 C2 N1 -3.2(2) . . . . ? C5 C3 C2 C8 0.8(3) . . . . ? C4 C3 C2 C8 178.53(17) . . . . ? C1 N1 C2 C3 -16.9(3) . . . . ? C1 N1 C2 C8 161.60(17) . . . . ? C1 N2 C4 C3 -32.3(2) . . . . ? C1 N2 C4 C9 93.05(19) . . . . ? C2 C3 C4 N2 24.6(2) . . . . ? C5 C3 C4 N2 -157.48(14) . . . . ? C2 C3 C4 C9 -98.72(18) . . . . ? C5 C3 C4 C9 79.24(18) . . . . ? C14 C9 C4 N2 -105.93(18) . . . . ? C10 C9 C4 N2 72.78(19) . . . . ? C14 C9 C4 C3 16.7(2) . . . . ? C10 C9 C4 C3 -164.57(15) . . . . ? C10 C9 C14 C13 -0.5(3) . . . . ? C4 C9 C14 C13 178.24(17) . . . . ? C6 O2 C5 O1 1.8(3) . . . . ? C6 O2 C5 C3 179.37(16) . . . . ? C2 C3 C5 O1 -156.82(18) . . . . ? C4 C3 C5 O1 25.3(2) . . . . ? C2 C3 C5 O2 25.6(3) . . . . ? C4 C3 C5 O2 -152.23(15) . . . . ? C14 C9 C10 C11 0.8(3) . . . . ? C4 C9 C10 C11 -177.95(17) . . . . ? C5 O2 C6 C7 -173.4(2) . . . . ? C9 C14 C13 C12 -0.1(3) . . . . ? C14 C13 C12 F1 -179.70(19) . . . . ? C14 C13 C12 C11 0.4(3) . . . . ? F1 C12 C11 C10 -179.96(18) . . . . ? C13 C12 C11 C10 -0.1(3) . . . . ? C9 C10 C11 C12 -0.6(3) . . . . ? #===END # Attachment 'PYR4.txt' # CIF-file generated for PYR4 in P-1 #============================================================================== data_vsk17_m _database_code_depnum_ccdc_archive 'CCDC 732836' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 6-Methyl-2-thioxo-4-p-tolyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester ; _chemical_name_common ; 6-Methyl-2-thioxo-4-p-tolyl-1,2,3,4-tetrahydro-pyrimidine-5- carboxylic acid ethy ; _chemical_melting_point ? _chemical_formula_moiety 'C15 H18 N2 O2 S' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C15 H18 N2 O2 S' _chemical_formula_iupac ? _chemical_formula_weight 290.38 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' N N 0.0061 0.0033 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 7.3550(9) _cell_length_b 9.4652(12) _cell_length_c 12.2073(16) _cell_angle_alpha 74.218(2) _cell_angle_beta 88.672(2) _cell_angle_gamma 69.844(2) _cell_volume 765.37(17) _cell_formula_units_Z 2 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 300 _cell_measurement_theta_min 27.97 _cell_measurement_theta_max 0.90 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.15 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.214 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9201 _exptl_absorpt_correction_T_max 0.9686 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 7983 _diffrn_reflns_av_R_equivalents 0.0149 _diffrn_reflns_av_sigmaI/netI 0.0177 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 26.00 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2978 # number of observed reflections (> n sig(I)) _reflns_number_gt 2521 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0604P)^2^+0.2220P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2978 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0497 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1158 _refine_ls_wR_factor_gt 0.1113 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.292 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.044 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.19804(7) 0.09767(6) 0.54398(4) 0.04549(17) Uani 1 1 d . . . N2 N 0.5138(2) 0.15929(17) 0.58073(13) 0.0379(3) Uani 1 1 d . . . H2N H 0.5706 0.1002 0.5385 0.045 Uiso 1 1 calc R . . N1 N 0.2313(2) 0.31662(17) 0.62988(13) 0.0372(3) Uani 1 1 d . . . H1N H 0.1126 0.3323 0.6458 0.045 Uiso 1 1 calc R . . O2 O 0.53194(19) 0.57723(17) 0.72223(14) 0.0549(4) Uani 1 1 d . . . O1 O 0.79262(18) 0.44425(16) 0.64798(13) 0.0514(4) Uani 1 1 d . . . C3 C 0.5123(2) 0.37587(19) 0.65154(14) 0.0336(4) Uani 1 1 d . . . C1 C 0.3237(2) 0.1935(2) 0.58747(14) 0.0336(4) Uani 1 1 d . . . C5 C 0.6265(2) 0.4684(2) 0.67104(15) 0.0366(4) Uani 1 1 d . . . C2 C 0.3173(2) 0.4186(2) 0.64905(14) 0.0342(4) Uani 1 1 d . . . C4 C 0.6338(2) 0.21568(19) 0.64072(14) 0.0331(4) Uani 1 1 d . . . H4 H 0.7406 0.2268 0.5938 0.040 Uiso 1 1 calc R . . C9 C 0.7216(2) 0.0964(2) 0.75525(14) 0.0342(4) Uani 1 1 d . . . C8 C 0.1724(3) 0.5677(2) 0.6625(2) 0.0495(5) Uani 1 1 d . . . H8A H 0.1482 0.5552 0.7416 0.074 Uiso 1 1 calc R . . H8B H 0.0534 0.5926 0.6185 0.074 Uiso 1 1 calc R . . H8C H 0.2227 0.6512 0.6361 0.074 Uiso 1 1 calc R . . C14 C 0.6487(3) 0.1140(2) 0.85799(16) 0.0460(4) Uani 1 1 d . . . H14 H 0.5429 0.2029 0.8587 0.055 Uiso 1 1 calc R . . C6 C 0.6315(3) 0.6742(2) 0.7479(2) 0.0532(5) Uani 1 1 d . . . H6A H 0.6472 0.7465 0.6781 0.064 Uiso 1 1 calc R . . H6B H 0.7591 0.6092 0.7858 0.064 Uiso 1 1 calc R . . C10 C 0.8797(3) -0.0379(2) 0.75785(17) 0.0450(4) Uani 1 1 d . . . H10 H 0.9330 -0.0523 0.6901 0.054 Uiso 1 1 calc R . . C12 C 0.8853(3) -0.1329(3) 0.96285(18) 0.0526(5) Uani 1 1 d . . . C11 C 0.9586(3) -0.1503(2) 0.85991(19) 0.0545(5) Uani 1 1 d . . . H11 H 1.0635 -0.2398 0.8595 0.065 Uiso 1 1 calc R . . C13 C 0.7307(3) 0.0012(3) 0.96016(18) 0.0557(5) Uani 1 1 d . . . H13 H 0.6801 0.0166 1.0282 0.067 Uiso 1 1 calc R . . C15 C 0.9708(4) -0.2568(3) 1.0744(2) 0.0841(8) Uani 1 1 d . . . H15A H 0.9486 -0.2089 1.1357 0.126 Uiso 1 1 calc R . . H15B H 1.1079 -0.3060 1.0708 0.126 Uiso 1 1 calc R . . H15C H 0.9100 -0.3343 1.0875 0.126 Uiso 1 1 calc R . . C7 C 0.5122(4) 0.7607(4) 0.8226(3) 0.0840(9) Uani 1 1 d . . . H7A H 0.3842 0.8199 0.7859 0.126 Uiso 1 1 calc R . . H7B H 0.5702 0.8308 0.8378 0.126 Uiso 1 1 calc R . . H7C H 0.5042 0.6881 0.8932 0.126 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0353(3) 0.0514(3) 0.0611(3) -0.0312(2) 0.0049(2) -0.0175(2) N2 0.0296(7) 0.0440(8) 0.0456(8) -0.0261(7) 0.0034(6) -0.0093(6) N1 0.0265(7) 0.0434(8) 0.0494(8) -0.0244(7) 0.0095(6) -0.0136(6) O2 0.0393(7) 0.0586(9) 0.0904(11) -0.0482(8) 0.0183(7) -0.0261(7) O1 0.0310(7) 0.0568(8) 0.0793(10) -0.0339(7) 0.0135(6) -0.0203(6) C3 0.0285(8) 0.0357(9) 0.0397(9) -0.0158(7) 0.0042(7) -0.0111(7) C1 0.0314(8) 0.0365(9) 0.0339(8) -0.0132(7) 0.0024(6) -0.0106(7) C5 0.0320(9) 0.0355(9) 0.0430(9) -0.0131(7) 0.0035(7) -0.0111(7) C2 0.0312(8) 0.0351(9) 0.0401(9) -0.0156(7) 0.0052(7) -0.0127(7) C4 0.0255(8) 0.0384(9) 0.0400(9) -0.0178(7) 0.0059(6) -0.0117(7) C9 0.0280(8) 0.0387(9) 0.0420(9) -0.0175(7) 0.0039(7) -0.0147(7) C8 0.0308(9) 0.0432(11) 0.0770(14) -0.0277(10) 0.0057(9) -0.0080(8) C14 0.0437(10) 0.0491(11) 0.0470(11) -0.0213(9) 0.0082(8) -0.0130(9) C6 0.0477(11) 0.0524(12) 0.0780(15) -0.0338(11) 0.0110(10) -0.0287(10) C10 0.0350(9) 0.0492(11) 0.0483(11) -0.0169(9) 0.0065(8) -0.0092(8) C12 0.0492(11) 0.0573(12) 0.0503(12) -0.0047(9) -0.0071(9) -0.0250(10) C11 0.0374(10) 0.0474(11) 0.0665(14) -0.0079(10) -0.0030(9) -0.0058(9) C13 0.0658(14) 0.0669(14) 0.0414(11) -0.0193(10) 0.0079(9) -0.0290(11) C15 0.0866(19) 0.0852(19) 0.0639(16) 0.0110(14) -0.0184(14) -0.0331(16) C7 0.0711(17) 0.100(2) 0.124(2) -0.0776(19) 0.0329(16) -0.0495(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.6800(17) . ? N2 C1 1.328(2) . ? N2 C4 1.472(2) . ? N2 H2N 0.8600 . ? N1 C1 1.361(2) . ? N1 C2 1.392(2) . ? N1 H1N 0.8600 . ? O2 C5 1.331(2) . ? O2 C6 1.451(2) . ? O1 C5 1.205(2) . ? C3 C2 1.348(2) . ? C3 C5 1.469(2) . ? C3 C4 1.512(2) . ? C2 C8 1.495(2) . ? C4 C9 1.525(2) . ? C4 H4 0.9800 . ? C9 C14 1.382(2) . ? C9 C10 1.390(2) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C14 C13 1.388(3) . ? C14 H14 0.9300 . ? C6 C7 1.465(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C10 C11 1.381(3) . ? C10 H10 0.9300 . ? C12 C13 1.374(3) . ? C12 C11 1.384(3) . ? C12 C15 1.513(3) . ? C11 H11 0.9300 . ? C13 H13 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N2 C4 124.41(14) . . ? C1 N2 H2N 117.8 . . ? C4 N2 H2N 117.8 . . ? C1 N1 C2 123.92(14) . . ? C1 N1 H1N 118.0 . . ? C2 N1 H1N 118.0 . . ? C5 O2 C6 118.47(14) . . ? C2 C3 C5 125.94(15) . . ? C2 C3 C4 119.91(15) . . ? C5 C3 C4 114.05(13) . . ? N2 C1 N1 115.82(15) . . ? N2 C1 S1 123.66(13) . . ? N1 C1 S1 120.50(12) . . ? O1 C5 O2 122.79(16) . . ? O1 C5 C3 123.65(16) . . ? O2 C5 C3 113.48(14) . . ? C3 C2 N1 118.77(15) . . ? C3 C2 C8 128.32(16) . . ? N1 C2 C8 112.90(14) . . ? N2 C4 C3 108.93(13) . . ? N2 C4 C9 110.46(13) . . ? C3 C4 C9 113.24(13) . . ? N2 C4 H4 108.0 . . ? C3 C4 H4 108.0 . . ? C9 C4 H4 108.0 . . ? C14 C9 C10 117.72(17) . . ? C14 C9 C4 122.88(15) . . ? C10 C9 C4 119.39(15) . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C9 C14 C13 121.02(18) . . ? C9 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? O2 C6 C7 107.24(16) . . ? O2 C6 H6A 110.3 . . ? C7 C6 H6A 110.3 . . ? O2 C6 H6B 110.3 . . ? C7 C6 H6B 110.3 . . ? H6A C6 H6B 108.5 . . ? C11 C10 C9 120.71(18) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C13 C12 C11 117.54(19) . . ? C13 C12 C15 121.0(2) . . ? C11 C12 C15 121.5(2) . . ? C10 C11 C12 121.61(19) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C12 C13 C14 121.4(2) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N2 C1 N1 16.2(2) . . . . ? C4 N2 C1 S1 -165.53(13) . . . . ? C2 N1 C1 N2 10.0(2) . . . . ? C2 N1 C1 S1 -168.40(13) . . . . ? C6 O2 C5 O1 2.1(3) . . . . ? C6 O2 C5 C3 178.88(16) . . . . ? C2 C3 C5 O1 -162.84(19) . . . . ? C4 C3 C5 O1 20.9(2) . . . . ? C2 C3 C5 O2 20.4(3) . . . . ? C4 C3 C5 O2 -155.90(15) . . . . ? C5 C3 C2 N1 -179.76(15) . . . . ? C4 C3 C2 N1 -3.7(2) . . . . ? C5 C3 C2 C8 1.5(3) . . . . ? C4 C3 C2 C8 177.56(17) . . . . ? C1 N1 C2 C3 -15.9(3) . . . . ? C1 N1 C2 C8 163.08(17) . . . . ? C1 N2 C4 C3 -31.9(2) . . . . ? C1 N2 C4 C9 93.08(19) . . . . ? C2 C3 C4 N2 24.3(2) . . . . ? C5 C3 C4 N2 -159.14(14) . . . . ? C2 C3 C4 C9 -99.02(18) . . . . ? C5 C3 C4 C9 77.53(18) . . . . ? N2 C4 C9 C14 -101.94(18) . . . . ? C3 C4 C9 C14 20.6(2) . . . . ? N2 C4 C9 C10 76.80(18) . . . . ? C3 C4 C9 C10 -160.71(15) . . . . ? C10 C9 C14 C13 0.0(3) . . . . ? C4 C9 C14 C13 178.76(17) . . . . ? C5 O2 C6 C7 -169.1(2) . . . . ? C14 C9 C10 C11 0.8(3) . . . . ? C4 C9 C10 C11 -177.99(17) . . . . ? C9 C10 C11 C12 -0.7(3) . . . . ? C13 C12 C11 C10 -0.2(3) . . . . ? C15 C12 C11 C10 179.4(2) . . . . ? C11 C12 C13 C14 1.1(3) . . . . ? C15 C12 C13 C14 -178.6(2) . . . . ? C9 C14 C13 C12 -1.0(3) . . . . ? #===END # Attachment 'PYR3.txt' # CIF-file generated for PYR3 in P-1 #============================================================================== data_s3cl_m _database_code_depnum_ccdc_archive 'CCDC 732837' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 4-(3-Chloro-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester ; _chemical_name_common ; 4-(3-Chloro-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro- pyrimidine-5-carboxylic ; _chemical_melting_point ? _chemical_formula_moiety 'C14 H15 Cl N2 O2 S' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C14 H15 Cl N2 O2 S' _chemical_formula_iupac ? _chemical_formula_weight 310.80 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 7.294(3) _cell_length_b 10.430(4) _cell_length_c 10.634(4) _cell_angle_alpha 107.600(6) _cell_angle_beta 90.610(6) _cell_angle_gamma 107.820(6) _cell_volume 729.4(5) _cell_formula_units_Z 2 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 350 _cell_measurement_theta_min 27.99 _cell_measurement_theta_max 0.92 _cell_special_details ; ; _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.407 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.8808 _exptl_absorpt_correction_T_max 0.9303 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 6999 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 25.00 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2569 # number of observed reflections (> n sig(I)) _reflns_number_gt 2155 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1188P)^2^+0.3119P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2569 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0747 _refine_ls_R_factor_gt 0.0653 _refine_ls_wR_factor_ref 0.1844 _refine_ls_wR_factor_gt 0.1745 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.696 _refine_diff_density_min -0.377 _refine_diff_density_rms 0.099 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 1.30672(11) 0.59534(9) 0.95848(9) 0.0446(3) Uani 1 1 d . . . Cl1 Cl 0.41826(16) 0.18687(10) 0.56682(11) 0.0720(4) Uani 1 1 d . . . O1 O 0.6727(3) 0.8884(2) 0.8302(2) 0.0475(6) Uani 1 1 d . . . O2 O 0.9328(3) 1.0296(2) 0.7745(3) 0.0489(6) Uani 1 1 d . . . N2 N 0.9807(3) 0.6452(3) 0.9122(2) 0.0355(6) Uani 1 1 d . . . H2N H 0.9278 0.5923 0.9588 0.043 Uiso 1 1 calc R . . N1 N 1.2546(3) 0.7902(3) 0.8646(2) 0.0348(6) Uani 1 1 d . . . H1N H 1.3735 0.8060 0.8488 0.042 Uiso 1 1 calc R . . C3 C 0.9659(4) 0.8399(3) 0.8373(3) 0.0327(6) Uani 1 1 d . . . C1 C 1.1704(4) 0.6781(3) 0.9084(3) 0.0326(6) Uani 1 1 d . . . C9 C 0.7781(4) 0.5853(3) 0.7049(3) 0.0320(6) Uani 1 1 d . . . C5 C 0.8432(4) 0.9214(3) 0.8161(3) 0.0341(6) Uani 1 1 d . . . C4 C 0.8552(4) 0.6937(3) 0.8417(3) 0.0317(6) Uani 1 1 d . . . H4 H 0.7447 0.7004 0.8919 0.038 Uiso 1 1 calc R . . C2 C 1.1608(4) 0.8805(3) 0.8439(3) 0.0321(6) Uani 1 1 d . . . C10 C 0.6459(4) 0.4533(3) 0.6966(3) 0.0387(7) Uani 1 1 d . . . H10 H 0.6029 0.4342 0.7731 0.046 Uiso 1 1 calc R . . C11 C 0.5805(4) 0.3528(3) 0.5757(3) 0.0418(7) Uani 1 1 d . . . C14 C 0.8365(4) 0.6099(3) 0.5890(3) 0.0409(7) Uani 1 1 d . . . H14 H 0.9255 0.6970 0.5929 0.049 Uiso 1 1 calc R . . C6 C 0.8190(5) 1.1114(3) 0.7460(4) 0.0454(8) Uani 1 1 d . . . H6A H 0.7769 1.1619 0.8268 0.054 Uiso 1 1 calc R . . H6B H 0.7054 1.0494 0.6841 0.054 Uiso 1 1 calc R . . C8 C 1.2981(4) 1.0155(3) 0.8316(4) 0.0460(8) Uani 1 1 d . . . H8A H 1.3126 1.0042 0.7397 0.069 Uiso 1 1 calc R . . H8B H 1.4220 1.0365 0.8791 0.069 Uiso 1 1 calc R . . H8C H 1.2476 1.0922 0.8683 0.069 Uiso 1 1 calc R . . C13 C 0.7648(5) 0.5072(4) 0.4679(3) 0.0475(8) Uani 1 1 d . . . H13 H 0.8038 0.5262 0.3906 0.057 Uiso 1 1 calc R . . C12 C 0.6361(5) 0.3765(4) 0.4598(3) 0.0475(8) Uani 1 1 d . . . H12 H 0.5882 0.3063 0.3781 0.057 Uiso 1 1 calc R . . C7 C 0.9460(7) 1.2129(6) 0.6873(7) 0.097(2) Uani 1 1 d . . . H7A H 1.0662 1.2638 0.7437 0.146 Uiso 1 1 calc R . . H7B H 0.8833 1.2789 0.6787 0.146 Uiso 1 1 calc R . . H7C H 0.9711 1.1620 0.6012 0.146 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0354(5) 0.0474(5) 0.0661(6) 0.0357(4) 0.0032(4) 0.0175(4) Cl1 0.0792(7) 0.0384(5) 0.0796(7) 0.0168(5) -0.0081(5) -0.0046(5) O1 0.0284(11) 0.0501(14) 0.0782(16) 0.0361(12) 0.0113(10) 0.0172(10) O2 0.0317(11) 0.0444(13) 0.0885(17) 0.0425(13) 0.0082(11) 0.0165(10) N2 0.0285(12) 0.0394(14) 0.0464(14) 0.0277(11) 0.0006(10) 0.0080(10) N1 0.0251(12) 0.0381(13) 0.0514(14) 0.0266(11) 0.0062(10) 0.0125(10) C3 0.0281(14) 0.0297(15) 0.0441(16) 0.0180(12) 0.0033(12) 0.0088(12) C1 0.0289(14) 0.0342(15) 0.0354(14) 0.0152(12) 0.0002(11) 0.0074(12) C9 0.0248(13) 0.0332(15) 0.0453(16) 0.0184(12) -0.0008(11) 0.0138(11) C5 0.0305(15) 0.0304(14) 0.0447(16) 0.0158(12) 0.0037(12) 0.0109(12) C4 0.0250(13) 0.0329(15) 0.0445(16) 0.0211(13) 0.0027(11) 0.0111(11) C2 0.0269(14) 0.0305(14) 0.0421(15) 0.0167(12) 0.0024(11) 0.0087(12) C10 0.0383(16) 0.0364(16) 0.0470(17) 0.0224(14) 0.0012(13) 0.0111(13) C11 0.0364(16) 0.0341(16) 0.0553(19) 0.0161(14) -0.0035(14) 0.0106(13) C14 0.0366(16) 0.0439(18) 0.0472(18) 0.0227(15) 0.0041(13) 0.0123(13) C6 0.0407(17) 0.0385(17) 0.069(2) 0.0265(16) 0.0050(15) 0.0208(14) C8 0.0276(15) 0.0403(18) 0.079(2) 0.0347(17) 0.0064(15) 0.0079(13) C13 0.0450(18) 0.059(2) 0.0455(18) 0.0245(16) 0.0082(14) 0.0197(16) C12 0.0455(18) 0.0461(19) 0.0471(18) 0.0053(15) -0.0029(15) 0.0196(16) C7 0.067(3) 0.092(4) 0.190(6) 0.109(4) 0.036(3) 0.041(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.676(3) . ? Cl1 C11 1.746(3) . ? O1 C5 1.208(4) . ? O2 C5 1.324(4) . ? O2 C6 1.447(4) . ? N2 C1 1.324(4) . ? N2 C4 1.468(3) . ? N2 H2N 0.8600 . ? N1 C1 1.363(4) . ? N1 C2 1.386(4) . ? N1 H1N 0.8600 . ? C3 C2 1.348(4) . ? C3 C5 1.467(4) . ? C3 C4 1.506(4) . ? C9 C14 1.379(4) . ? C9 C10 1.395(4) . ? C9 C4 1.519(4) . ? C4 H4 0.9800 . ? C2 C8 1.501(4) . ? C10 C11 1.358(5) . ? C10 H10 0.9300 . ? C11 C12 1.371(5) . ? C14 C13 1.374(5) . ? C14 H14 0.9300 . ? C6 C7 1.477(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C13 C12 1.375(5) . ? C13 H13 0.9300 . ? C12 H12 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O2 C6 117.6(2) . . ? C1 N2 C4 124.0(2) . . ? C1 N2 H2N 118.0 . . ? C4 N2 H2N 118.0 . . ? C1 N1 C2 124.1(2) . . ? C1 N1 H1N 117.9 . . ? C2 N1 H1N 117.9 . . ? C2 C3 C5 126.2(3) . . ? C2 C3 C4 119.4(3) . . ? C5 C3 C4 114.3(2) . . ? N2 C1 N1 115.6(2) . . ? N2 C1 S1 124.2(2) . . ? N1 C1 S1 120.2(2) . . ? C14 C9 C10 118.5(3) . . ? C14 C9 C4 123.1(3) . . ? C10 C9 C4 118.4(3) . . ? O1 C5 O2 123.1(3) . . ? O1 C5 C3 122.5(3) . . ? O2 C5 C3 114.3(2) . . ? N2 C4 C3 109.2(2) . . ? N2 C4 C9 109.7(2) . . ? C3 C4 C9 113.2(2) . . ? N2 C4 H4 108.2 . . ? C3 C4 H4 108.2 . . ? C9 C4 H4 108.2 . . ? C3 C2 N1 118.8(2) . . ? C3 C2 C8 128.4(3) . . ? N1 C2 C8 112.8(2) . . ? C11 C10 C9 119.4(3) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C10 C11 C12 122.6(3) . . ? C10 C11 Cl1 119.0(3) . . ? C12 C11 Cl1 118.5(3) . . ? C13 C14 C9 120.8(3) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? O2 C6 C7 106.5(3) . . ? O2 C6 H6A 110.4 . . ? C7 C6 H6A 110.4 . . ? O2 C6 H6B 110.4 . . ? C7 C6 H6B 110.4 . . ? H6A C6 H6B 108.6 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C13 C12 120.7(3) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C11 C12 C13 118.0(3) . . ? C11 C12 H12 121.0 . . ? C13 C12 H12 121.0 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N2 C1 N1 17.0(4) . . . . ? C4 N2 C1 S1 -165.5(2) . . . . ? C2 N1 C1 N2 9.7(4) . . . . ? C2 N1 C1 S1 -168.0(2) . . . . ? C6 O2 C5 O1 0.5(5) . . . . ? C6 O2 C5 C3 177.4(3) . . . . ? C2 C3 C5 O1 -169.1(3) . . . . ? C4 C3 C5 O1 15.5(4) . . . . ? C2 C3 C5 O2 13.9(4) . . . . ? C4 C3 C5 O2 -161.5(3) . . . . ? C1 N2 C4 C3 -33.5(4) . . . . ? C1 N2 C4 C9 91.2(3) . . . . ? C2 C3 C4 N2 26.0(4) . . . . ? C5 C3 C4 N2 -158.3(2) . . . . ? C2 C3 C4 C9 -96.5(3) . . . . ? C5 C3 C4 C9 79.2(3) . . . . ? C14 C9 C4 N2 -109.6(3) . . . . ? C10 C9 C4 N2 68.6(3) . . . . ? C14 C9 C4 C3 12.7(4) . . . . ? C10 C9 C4 C3 -169.1(2) . . . . ? C5 C3 C2 N1 180.0(3) . . . . ? C4 C3 C2 N1 -4.9(4) . . . . ? C5 C3 C2 C8 0.1(5) . . . . ? C4 C3 C2 C8 175.2(3) . . . . ? C1 N1 C2 C3 -15.4(4) . . . . ? C1 N1 C2 C8 164.5(3) . . . . ? C14 C9 C10 C11 0.7(4) . . . . ? C4 C9 C10 C11 -177.6(3) . . . . ? C9 C10 C11 C12 -1.4(5) . . . . ? C9 C10 C11 Cl1 178.9(2) . . . . ? C10 C9 C14 C13 0.6(4) . . . . ? C4 C9 C14 C13 178.8(3) . . . . ? C5 O2 C6 C7 -173.5(4) . . . . ? C9 C14 C13 C12 -1.3(5) . . . . ? C10 C11 C12 C13 0.7(5) . . . . ? Cl1 C11 C12 C13 -179.6(3) . . . . ? C14 C13 C12 C11 0.7(5) . . . . ? #===END # Attachment 'PYR8.txt' # CIF-file generated for PYR8 in P-1 #============================================================================== data_s234oc _database_code_depnum_ccdc_archive 'CCDC 732838' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 4-(2,3,4-trimethoxy-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5- carboxylic acid ethyl ester ; _chemical_name_common ; 4-(2,3,4-trimethoxy-phenyl)-6-methyl-2-thioxo-1,2,3,4- tetrahydro-pyrimidine-5-carboxylic acid ethyl ester ; _chemical_melting_point ? _chemical_formula_moiety 'C17 H22 N2 O5 S' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C17 H22 N2 O5 S' _chemical_formula_iupac ? _chemical_formula_weight 366.44 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' N N 0.0061 0.0033 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 8.0235(3) _cell_length_b 10.6374(5) _cell_length_c 11.8171(4) _cell_angle_alpha 84.489(3) _cell_angle_beta 74.115(3) _cell_angle_gamma 69.045(4) _cell_volume 905.90(7) _cell_formula_units_Z 2 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 360 _cell_measurement_theta_min 0.92 _cell_measurement_theta_max 27.97 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.28 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.208 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996' _exptl_absorpt_correction_T_min 0.9077 _exptl_absorpt_correction_T_max 0.9440 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 18202 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0188 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 25.99 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 3553 # number of observed reflections (> n sig(I)) _reflns_number_gt 2942 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0552P)^2^+0.1764P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3553 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.1084 _refine_ls_wR_factor_gt 0.1053 _refine_ls_goodness_of_fit_ref 1.115 _refine_ls_restrained_S_all 1.115 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.218 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.041 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 1.29885(6) 0.38119(5) 0.46520(4) 0.04382(15) Uani 1 1 d . . . N2 N 1.07583(18) 0.52194(13) 0.65641(11) 0.0344(3) Uani 1 1 d . . . H2N H 0.9872 0.5223 0.6286 0.041 Uiso 1 1 calc R . . C1 C 1.2450(2) 0.44938(16) 0.59901(13) 0.0343(3) Uani 1 1 d . . . O5 O 0.65644(16) 0.77746(12) 0.78368(11) 0.0464(3) Uani 1 1 d . . . O3 O 0.82617(16) 1.15821(11) 0.64500(11) 0.0486(3) Uani 1 1 d . . . C9 C 0.9759(2) 0.75140(15) 0.73283(12) 0.0309(3) Uani 1 1 d . . . C4 C 1.0241(2) 0.60239(15) 0.76355(13) 0.0316(3) Uani 1 1 d . . . H4 H 0.9143 0.5892 0.8169 0.038 Uiso 1 1 calc R . . O4 O 0.56404(15) 1.05238(12) 0.73752(11) 0.0454(3) Uani 1 1 d . . . N1 N 1.37906(19) 0.42875(16) 0.65609(12) 0.0454(4) Uani 1 1 d . . . H1N H 1.4910 0.3848 0.6192 0.055 Uiso 1 1 calc R . . O2 O 0.95430(17) 0.67214(12) 0.98480(10) 0.0476(3) Uani 1 1 d . . . C11 C 0.7461(2) 0.97024(15) 0.71999(13) 0.0342(3) Uani 1 1 d . . . C10 C 0.7917(2) 0.83414(15) 0.74800(13) 0.0328(3) Uani 1 1 d . . . C5 C 1.1359(3) 0.60265(17) 0.94560(14) 0.0431(4) Uani 1 1 d . . . C13 C 1.0683(2) 0.94251(16) 0.65666(15) 0.0389(4) Uani 1 1 d . . . H13 H 1.1620 0.9778 0.6255 0.047 Uiso 1 1 calc R . . C14 C 1.1118(2) 0.80759(16) 0.68676(14) 0.0362(4) Uani 1 1 d . . . H14 H 1.2352 0.7534 0.6758 0.043 Uiso 1 1 calc R . . C3 C 1.1790(2) 0.55345(15) 0.82495(13) 0.0337(3) Uani 1 1 d . . . C12 C 0.8856(2) 1.02470(15) 0.67294(14) 0.0358(4) Uani 1 1 d . . . C2 C 1.3487(2) 0.47344(16) 0.76956(14) 0.0374(4) Uani 1 1 d . . . C15 C 0.9638(3) 1.21794(18) 0.59575(17) 0.0492(4) Uani 1 1 d . . . H15A H 1.0332 1.2131 0.6516 0.074 Uiso 1 1 calc R . . H15B H 0.9054 1.3105 0.5772 0.074 Uiso 1 1 calc R . . H15C H 1.0455 1.1704 0.5254 0.074 Uiso 1 1 calc R . . O1 O 1.2416(2) 0.58596(19) 1.00499(13) 0.0803(5) Uani 1 1 d . . . C8 C 1.5187(3) 0.4226(2) 0.81418(17) 0.0557(5) Uani 1 1 d . . . H8A H 1.4865 0.4456 0.8959 0.084 Uiso 1 1 calc R . . H8B H 1.6061 0.4630 0.7701 0.084 Uiso 1 1 calc R . . H8C H 1.5724 0.3265 0.8052 0.084 Uiso 1 1 calc R . . C6 C 0.8961(3) 0.7446(2) 1.09470(16) 0.0568(5) Uani 1 1 d . . . H6A H 0.9625 0.6899 1.1498 0.068 Uiso 1 1 calc R . . H6B H 0.7652 0.7631 1.1289 0.068 Uiso 1 1 calc R . . C17 C 0.5371(3) 0.8125(3) 0.8987(2) 0.0780(7) Uani 1 1 d . . . H17A H 0.6038 0.7700 0.9563 0.117 Uiso 1 1 calc R . . H17B H 0.4343 0.7825 0.9087 0.117 Uiso 1 1 calc R . . H17C H 0.4927 0.9084 0.9085 0.117 Uiso 1 1 calc R . . C16 C 0.4947(3) 1.0563(3) 0.6389(2) 0.0720(6) Uani 1 1 d . . . H16A H 0.5672 1.0881 0.5716 0.108 Uiso 1 1 calc R . . H16B H 0.3685 1.1160 0.6549 0.108 Uiso 1 1 calc R . . H16C H 0.5011 0.9676 0.6233 0.108 Uiso 1 1 calc R . . C7 C 0.9330(4) 0.8725(2) 1.0738(2) 0.0873(8) Uani 1 1 d . . . H7A H 1.0639 0.8538 1.0515 0.131 Uiso 1 1 calc R . . H7B H 0.8784 0.9256 1.1444 0.131 Uiso 1 1 calc R . . H7C H 0.8806 0.9212 1.0118 0.131 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0454(3) 0.0520(3) 0.0337(2) -0.00726(18) -0.01265(18) -0.0127(2) N2 0.0352(7) 0.0356(7) 0.0369(7) -0.0033(5) -0.0174(6) -0.0106(6) C1 0.0386(9) 0.0350(8) 0.0337(8) 0.0036(6) -0.0131(7) -0.0161(7) O5 0.0357(6) 0.0483(7) 0.0572(7) 0.0022(6) -0.0073(5) -0.0209(5) O3 0.0450(7) 0.0296(6) 0.0662(8) 0.0022(5) -0.0089(6) -0.0117(5) C9 0.0331(8) 0.0329(8) 0.0281(7) -0.0008(6) -0.0105(6) -0.0109(6) C4 0.0342(8) 0.0324(8) 0.0298(7) 0.0004(6) -0.0104(6) -0.0118(6) O4 0.0310(6) 0.0426(7) 0.0534(7) -0.0027(5) -0.0089(5) -0.0027(5) N1 0.0317(7) 0.0650(10) 0.0376(7) -0.0112(7) -0.0114(6) -0.0097(7) O2 0.0531(8) 0.0513(7) 0.0353(6) -0.0091(5) -0.0095(5) -0.0137(6) C11 0.0292(8) 0.0350(8) 0.0351(8) -0.0043(6) -0.0073(6) -0.0068(6) C10 0.0323(8) 0.0380(8) 0.0306(7) -0.0018(6) -0.0079(6) -0.0148(7) C5 0.0524(11) 0.0428(10) 0.0375(9) 0.0004(7) -0.0181(8) -0.0158(8) C13 0.0348(8) 0.0387(9) 0.0457(9) -0.0003(7) -0.0079(7) -0.0174(7) C14 0.0301(8) 0.0360(8) 0.0418(9) -0.0013(7) -0.0106(7) -0.0092(7) C3 0.0405(9) 0.0328(8) 0.0320(8) 0.0038(6) -0.0160(7) -0.0136(7) C12 0.0389(9) 0.0291(8) 0.0384(8) -0.0026(6) -0.0097(7) -0.0103(7) C2 0.0393(9) 0.0420(9) 0.0349(8) 0.0023(7) -0.0170(7) -0.0138(7) C15 0.0577(11) 0.0371(9) 0.0561(11) 0.0051(8) -0.0140(9) -0.0221(8) O1 0.0688(10) 0.1124(13) 0.0571(9) -0.0271(8) -0.0381(8) -0.0051(9) C8 0.0440(10) 0.0696(13) 0.0527(11) -0.0052(9) -0.0251(9) -0.0080(9) C6 0.0771(14) 0.0523(11) 0.0379(9) -0.0101(8) -0.0034(9) -0.0245(10) C17 0.0602(13) 0.0936(18) 0.0681(14) 0.0099(13) 0.0108(11) -0.0353(13) C16 0.0489(12) 0.0851(17) 0.0759(15) 0.0028(12) -0.0320(11) -0.0050(11) C7 0.121(2) 0.0606(14) 0.0755(16) -0.0181(12) 0.0026(15) -0.0417(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.6838(16) . ? N2 C1 1.321(2) . ? N2 C4 1.4745(18) . ? N2 H2N 0.8600 . ? C1 N1 1.364(2) . ? O5 C10 1.3738(18) . ? O5 C17 1.425(2) . ? O3 C12 1.3656(18) . ? O3 C15 1.429(2) . ? C9 C14 1.386(2) . ? C9 C10 1.395(2) . ? C9 C4 1.524(2) . ? C4 C3 1.516(2) . ? C4 H4 0.9800 . ? O4 C11 1.3773(18) . ? O4 C16 1.413(2) . ? N1 C2 1.394(2) . ? N1 H1N 0.8600 . ? O2 C5 1.346(2) . ? O2 C6 1.450(2) . ? C11 C10 1.391(2) . ? C11 C12 1.399(2) . ? C5 O1 1.199(2) . ? C5 C3 1.473(2) . ? C13 C12 1.383(2) . ? C13 C14 1.386(2) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C3 C2 1.341(2) . ? C2 C8 1.497(2) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C6 C7 1.477(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N2 C4 126.34(13) . . ? C1 N2 H2N 116.8 . . ? C4 N2 H2N 116.8 . . ? N2 C1 N1 115.78(14) . . ? N2 C1 S1 124.00(12) . . ? N1 C1 S1 120.20(12) . . ? C10 O5 C17 116.44(15) . . ? C12 O3 C15 117.37(13) . . ? C14 C9 C10 118.34(14) . . ? C14 C9 C4 121.50(13) . . ? C10 C9 C4 120.14(13) . . ? N2 C4 C3 109.87(12) . . ? N2 C4 C9 110.14(11) . . ? C3 C4 C9 111.99(12) . . ? N2 C4 H4 108.2 . . ? C3 C4 H4 108.2 . . ? C9 C4 H4 108.2 . . ? C11 O4 C16 112.67(14) . . ? C1 N1 C2 125.07(14) . . ? C1 N1 H1N 117.5 . . ? C2 N1 H1N 117.5 . . ? C5 O2 C6 116.68(14) . . ? O4 C11 C10 120.50(14) . . ? O4 C11 C12 119.41(14) . . ? C10 C11 C12 120.10(14) . . ? O5 C10 C11 120.33(13) . . ? O5 C10 C9 118.93(13) . . ? C11 C10 C9 120.60(14) . . ? O1 C5 O2 122.03(16) . . ? O1 C5 C3 127.33(17) . . ? O2 C5 C3 110.64(14) . . ? C12 C13 C14 119.98(14) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C9 121.60(14) . . ? C13 C14 H14 119.2 . . ? C9 C14 H14 119.2 . . ? C2 C3 C5 121.95(14) . . ? C2 C3 C4 121.09(14) . . ? C5 C3 C4 116.91(14) . . ? O3 C12 C13 125.24(14) . . ? O3 C12 C11 115.39(14) . . ? C13 C12 C11 119.36(14) . . ? C3 C2 N1 118.92(14) . . ? C3 C2 C8 128.05(15) . . ? N1 C2 C8 113.03(14) . . ? O3 C15 H15A 109.5 . . ? O3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C6 C7 110.00(16) . . ? O2 C6 H6A 109.7 . . ? C7 C6 H6A 109.7 . . ? O2 C6 H6B 109.7 . . ? C7 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? O5 C17 H17A 109.5 . . ? O5 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O5 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O4 C16 H16A 109.5 . . ? O4 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O4 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N2 C1 N1 12.3(2) . . . . ? C4 N2 C1 S1 -169.14(11) . . . . ? C1 N2 C4 C3 -20.3(2) . . . . ? C1 N2 C4 C9 103.49(16) . . . . ? C14 C9 C4 N2 -79.98(17) . . . . ? C10 C9 C4 N2 98.40(15) . . . . ? C14 C9 C4 C3 42.61(19) . . . . ? C10 C9 C4 C3 -139.02(14) . . . . ? N2 C1 N1 C2 2.6(2) . . . . ? S1 C1 N1 C2 -176.01(13) . . . . ? C16 O4 C11 C10 -89.10(19) . . . . ? C16 O4 C11 C12 90.51(19) . . . . ? C17 O5 C10 C11 -72.2(2) . . . . ? C17 O5 C10 C9 112.05(18) . . . . ? O4 C11 C10 O5 5.8(2) . . . . ? C12 C11 C10 O5 -173.83(14) . . . . ? O4 C11 C10 C9 -178.54(13) . . . . ? C12 C11 C10 C9 1.9(2) . . . . ? C14 C9 C10 O5 174.31(13) . . . . ? C4 C9 C10 O5 -4.1(2) . . . . ? C14 C9 C10 C11 -1.4(2) . . . . ? C4 C9 C10 C11 -179.86(13) . . . . ? C6 O2 C5 O1 9.7(3) . . . . ? C6 O2 C5 C3 -170.51(13) . . . . ? C12 C13 C14 C9 0.3(2) . . . . ? C10 C9 C14 C13 0.3(2) . . . . ? C4 C9 C14 C13 178.75(14) . . . . ? O1 C5 C3 C2 4.5(3) . . . . ? O2 C5 C3 C2 -175.24(14) . . . . ? O1 C5 C3 C4 -172.88(18) . . . . ? O2 C5 C3 C4 7.4(2) . . . . ? N2 C4 C3 C2 15.2(2) . . . . ? C9 C4 C3 C2 -107.59(16) . . . . ? N2 C4 C3 C5 -167.42(13) . . . . ? C9 C4 C3 C5 69.84(17) . . . . ? C15 O3 C12 C13 -0.5(2) . . . . ? C15 O3 C12 C11 -179.49(14) . . . . ? C14 C13 C12 O3 -178.95(15) . . . . ? C14 C13 C12 C11 0.1(2) . . . . ? O4 C11 C12 O3 -1.7(2) . . . . ? C10 C11 C12 O3 177.96(13) . . . . ? O4 C11 C12 C13 179.24(14) . . . . ? C10 C11 C12 C13 -1.1(2) . . . . ? C5 C3 C2 N1 178.93(14) . . . . ? C4 C3 C2 N1 -3.8(2) . . . . ? C5 C3 C2 C8 -1.0(3) . . . . ? C4 C3 C2 C8 176.28(16) . . . . ? C1 N1 C2 C3 -6.5(3) . . . . ? C1 N1 C2 C8 173.46(16) . . . . ? C5 O2 C6 C7 79.7(2) . . . . ? #===END #===END # Attachment 'PYR2.txt' # CIF-file generated for PYR2 in P-1 #============================================================================== data_s2cl2 _database_code_depnum_ccdc_archive 'CCDC 734014' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 4-(2-chloro-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5- carboxylic acid ethyl ester ; _chemical_name_common ; 4-(2-chloro-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro- pyrimidine-5-carboxylic acid ethyl ester ; _chemical_melting_point ? _chemical_formula_moiety 'C14 H15 Cl N2 O2 S' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C14 H15 Cl N2 O2 S' _chemical_formula_iupac ? _chemical_formula_weight 310.80 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 11.534(5) _cell_length_b 12.540(5) _cell_length_c 12.618(5) _cell_angle_alpha 81.012(5) _cell_angle_beta 64.177(5) _cell_angle_gamma 64.737(5) _cell_volume 1484.7(11) _cell_formula_units_Z 4 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 400 _cell_measurement_theta_min 0.98 _cell_measurement_theta_max 27.99 _cell_special_details ; ; _exptl_crystal_description Rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.400 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.8962 _exptl_absorpt_correction_T_max 0.9461 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Goniometer Xcalibur, detector: Eos (Nova)' _diffrn_detector_area_resol_mean 16.0839 _diffrn_orient_matrix_UB_11 -0.0264070628 _diffrn_orient_matrix_UB_12 -0.0123140155 _diffrn_orient_matrix_UB_13 -0.0716751863 _diffrn_orient_matrix_UB_21 -0.0308146323 _diffrn_orient_matrix_UB_22 0.0292794918 _diffrn_orient_matrix_UB_23 -0.0115785972 _diffrn_orient_matrix_UB_31 0.0194441842 _diffrn_orient_matrix_UB_32 0.0295960308 _diffrn_orient_matrix_UB_33 -0.0176174689 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -68.00 -34.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -17.0427 179.0000 -180.0000 34 #__ type_ start__ end____ width___ exp.time_ 2 omega -78.00 -45.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -17.0427 179.0000 -150.0000 33 #__ type_ start__ end____ width___ exp.time_ 3 omega -79.00 2.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -17.0427 -77.0000 30.0000 81 #__ type_ start__ end____ width___ exp.time_ 4 omega 62.00 89.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 18.9177 77.0000 -180.0000 27 #__ type_ start__ end____ width___ exp.time_ 5 omega -10.00 19.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 18.9177 77.0000 -180.0000 29 #__ type_ start__ end____ width___ exp.time_ 6 omega -24.00 40.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 18.9177 -37.0000 30.0000 64 #__ type_ start__ end____ width___ exp.time_ 7 omega -90.00 9.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -17.0427 -37.0000 150.0000 99 #__ type_ start__ end____ width___ exp.time_ 8 omega -94.00 -34.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -17.0427 179.0000 -90.0000 60 #__ type_ start__ end____ width___ exp.time_ 9 omega -43.00 55.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -17.0427 37.0000 -30.0000 98 #__ type_ start__ end____ width___ exp.time_ 10 omega -11.00 89.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 18.9177 77.0000 -60.0000 100 #__ type_ start__ end____ width___ exp.time_ 11 omega -49.00 41.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 18.9177 -62.0000 178.0000 90 #__ type_ start__ end____ width___ exp.time_ 12 omega -85.00 5.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -17.0427 -62.0000 44.0000 90 #__ type_ start__ end____ width___ exp.time_ 13 omega -94.00 -34.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -17.0427 179.0000 30.0000 60 ; _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 22805 _diffrn_reflns_av_R_equivalents 0.0912 _diffrn_reflns_av_sigmaI/netI 0.0979 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 25.00 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 5214 # number of observed reflections (> n sig(I)) _reflns_number_gt 2745 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0576P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5214 _refine_ls_number_parameters 365 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1149 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.0944 _refine_ls_wR_factor_gt 0.0834 _refine_ls_goodness_of_fit_ref 0.864 _refine_ls_restrained_S_all 0.864 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.199 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.044 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1' S -0.10520(9) 0.15338(6) 0.91528(7) 0.0491(2) Uani 1 1 d . . . S1 S -0.10027(9) 0.43023(6) 0.67334(7) 0.0505(2) Uani 1 1 d . . . Cl1 Cl 0.00867(10) -0.10952(7) 0.68588(9) 0.0749(3) Uani 1 1 d . . . Cl1' Cl 0.03642(11) 0.58913(7) 0.80656(9) 0.0875(3) Uani 1 1 d . . . C11 C 0.2190(3) -0.1649(2) 0.7494(3) 0.0576(9) Uani 1 1 d . . . H11 H 0.1913 -0.2242 0.7911 0.069 Uiso 1 1 calc R . . O2 O 0.2543(2) -0.08302(15) 0.39001(17) 0.0527(6) Uani 1 1 d . . . O2' O 0.2998(2) 0.38595(18) 0.9317(2) 0.0723(7) Uani 1 1 d . . . N1 N 0.0969(3) 0.31384(18) 0.4730(2) 0.0446(7) Uani 1 1 d . . . H1N H 0.0894 0.3828 0.4461 0.054 Uiso 1 1 calc R . . O1 O 0.4014(2) -0.00496(17) 0.2621(2) 0.0625(6) Uani 1 1 d . . . O1' O 0.4108(2) 0.21161(18) 0.99121(19) 0.0646(7) Uani 1 1 d . . . N2' N 0.0253(2) 0.29161(18) 0.8879(2) 0.0476(7) Uani 1 1 d . . . H2N' H -0.0384 0.3415 0.8658 0.057 Uiso 1 1 calc R . . N2 N 0.0217(2) 0.20063(17) 0.6241(2) 0.0423(6) Uani 1 1 d . . . H2N H -0.0279 0.1959 0.6975 0.051 Uiso 1 1 calc R . . N1' N 0.1140(2) 0.11202(18) 0.9597(2) 0.0445(7) Uani 1 1 d . . . H1N' H 0.1123 0.0437 0.9797 0.053 Uiso 1 1 calc R . . C2' C 0.2160(3) 0.1357(2) 0.9707(2) 0.0411(8) Uani 1 1 d . . . C4' C 0.1295(3) 0.3315(2) 0.8851(3) 0.0408(8) Uani 1 1 d . . . H4' H 0.0788 0.4051 0.9327 0.049 Uiso 1 1 calc R . . C1' C 0.0176(3) 0.1882(2) 0.9202(2) 0.0392(7) Uani 1 1 d . . . C2 C 0.1950(3) 0.2176(2) 0.3969(3) 0.0376(7) Uani 1 1 d . . . C5 C 0.2980(3) 0.0048(2) 0.3511(3) 0.0415(8) Uani 1 1 d . . . C12 C 0.3294(4) -0.1520(3) 0.7521(3) 0.0607(10) Uani 1 1 d . . . H12 H 0.3765 -0.2027 0.7961 0.073 Uiso 1 1 calc R . . C3 C 0.2043(3) 0.1086(2) 0.4325(2) 0.0350(7) Uani 1 1 d . . . C10 C 0.1489(3) -0.0897(2) 0.6849(3) 0.0450(8) Uani 1 1 d . . . C3' C 0.2244(3) 0.2406(2) 0.9390(2) 0.0394(7) Uani 1 1 d . . . C4 C 0.1076(3) 0.0890(2) 0.5543(2) 0.0356(7) Uani 1 1 d . . . H4 H 0.0448 0.0602 0.5466 0.043 Uiso 1 1 calc R . . C5' C 0.3221(3) 0.2724(3) 0.9573(3) 0.0489(8) Uani 1 1 d . . . C1 C 0.0117(3) 0.3078(2) 0.5869(3) 0.0382(8) Uani 1 1 d . . . C13 C 0.3722(3) -0.0644(3) 0.6903(3) 0.0541(9) Uani 1 1 d . . . H13 H 0.4470 -0.0553 0.6928 0.065 Uiso 1 1 calc R . . C9 C 0.1875(3) -0.0004(2) 0.6220(2) 0.0348(7) Uani 1 1 d . . . C9' C 0.2092(3) 0.3574(2) 0.7590(3) 0.0409(8) Uani 1 1 d . . . C14 C 0.3011(3) 0.0091(2) 0.6250(3) 0.0468(8) Uani 1 1 d . . . H14 H 0.3305 0.0669 0.5817 0.056 Uiso 1 1 calc R . . C10' C 0.1734(4) 0.4692(3) 0.7152(3) 0.0562(9) Uani 1 1 d . . . C8' C 0.3086(3) 0.0354(2) 1.0174(3) 0.0571(9) Uani 1 1 d . . . H8'1 H 0.3895 -0.0143 0.9529 0.086 Uiso 1 1 calc R . . H8'2 H 0.2572 -0.0097 1.0677 0.086 Uiso 1 1 calc R . . H8'3 H 0.3386 0.0659 1.0615 0.086 Uiso 1 1 calc R . . C14' C 0.3204(3) 0.2665(3) 0.6811(3) 0.0574(9) Uani 1 1 d . . . H14' H 0.3484 0.1904 0.7084 0.069 Uiso 1 1 calc R . . C8 C 0.2792(3) 0.2505(2) 0.2781(3) 0.0553(9) Uani 1 1 d . . . H8A H 0.3341 0.1823 0.2254 0.083 Uiso 1 1 calc R . . H8B H 0.3407 0.2793 0.2847 0.083 Uiso 1 1 calc R . . H8C H 0.2167 0.3108 0.2478 0.083 Uiso 1 1 calc R . . C6 C 0.3295(4) -0.1880(2) 0.3138(3) 0.0658(10) Uani 1 1 d . . . H6A H 0.4287 -0.2033 0.2730 0.079 Uiso 1 1 calc R . . H6B H 0.2921 -0.1778 0.2556 0.079 Uiso 1 1 calc R . . C7 C 0.3103(4) -0.2873(3) 0.3900(3) 0.0821(12) Uani 1 1 d . . . H7A H 0.3608 -0.3048 0.4384 0.123 Uiso 1 1 calc R . . H7B H 0.3455 -0.3557 0.3416 0.123 Uiso 1 1 calc R . . H7C H 0.2120 -0.2658 0.4392 0.123 Uiso 1 1 calc R . . C13' C 0.3911(4) 0.2852(3) 0.5639(3) 0.0681(10) Uani 1 1 d . . . H13' H 0.4647 0.2227 0.5128 0.082 Uiso 1 1 calc R . . C11' C 0.2424(4) 0.4904(3) 0.5992(4) 0.0795(12) Uani 1 1 d . . . H11' H 0.2158 0.5667 0.5721 0.095 Uiso 1 1 calc R . . C6' C 0.3879(4) 0.4316(3) 0.9478(4) 0.0897(14) Uani 1 1 d . . . H6'1 H 0.3566 0.4466 1.0310 0.108 Uiso 1 1 calc R . . H6'2 H 0.4848 0.3742 0.9177 0.108 Uiso 1 1 calc R . . C12' C 0.3499(5) 0.3990(4) 0.5244(4) 0.0883(13) Uani 1 1 d . . . H12' H 0.3963 0.4131 0.4458 0.106 Uiso 1 1 calc R . . C7' C 0.3780(5) 0.5389(3) 0.8858(4) 0.1157(16) Uani 1 1 d . . . H7'1 H 0.4037 0.5243 0.8045 0.174 Uiso 1 1 calc R . . H7'2 H 0.4405 0.5672 0.8913 0.174 Uiso 1 1 calc R . . H7'3 H 0.2831 0.5971 0.9199 0.174 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1' 0.0536(6) 0.0540(5) 0.0483(6) 0.0191(4) -0.0249(5) -0.0308(4) S1 0.0635(6) 0.0326(4) 0.0465(6) 0.0061(4) -0.0219(5) -0.0140(4) Cl1 0.0743(7) 0.0760(6) 0.1000(8) 0.0446(5) -0.0489(6) -0.0532(5) Cl1' 0.1012(8) 0.0424(5) 0.0956(9) 0.0168(5) -0.0403(7) -0.0138(5) C11 0.064(2) 0.0477(18) 0.053(2) 0.0209(17) -0.025(2) -0.0210(18) O2 0.0596(15) 0.0369(11) 0.0558(16) -0.0026(11) -0.0146(13) -0.0226(11) O2' 0.0963(19) 0.0575(13) 0.103(2) 0.0252(13) -0.0689(18) -0.0451(14) N1 0.0589(18) 0.0297(13) 0.0381(18) 0.0132(13) -0.0168(15) -0.0192(13) O1 0.0605(16) 0.0510(13) 0.0588(18) -0.0070(12) -0.0033(14) -0.0264(13) O1' 0.0682(17) 0.0697(14) 0.0724(18) 0.0178(13) -0.0436(15) -0.0324(13) N2' 0.0466(17) 0.0404(13) 0.0620(19) 0.0217(13) -0.0321(15) -0.0198(13) N2 0.0514(17) 0.0340(13) 0.0342(16) 0.0105(12) -0.0146(14) -0.0173(12) N1' 0.0503(17) 0.0358(13) 0.0537(19) 0.0202(12) -0.0276(15) -0.0228(13) C2' 0.046(2) 0.0445(17) 0.033(2) 0.0104(14) -0.0174(17) -0.0205(16) C4' 0.050(2) 0.0368(15) 0.038(2) 0.0058(14) -0.0202(17) -0.0189(15) C1' 0.045(2) 0.0389(16) 0.031(2) 0.0070(14) -0.0142(17) -0.0180(15) C2 0.043(2) 0.0367(16) 0.032(2) 0.0041(15) -0.0167(17) -0.0145(16) C5 0.049(2) 0.0428(18) 0.041(2) 0.0085(17) -0.025(2) -0.0213(18) C12 0.065(3) 0.057(2) 0.058(3) 0.0181(18) -0.037(2) -0.0161(19) C3 0.0416(19) 0.0328(15) 0.033(2) 0.0057(14) -0.0169(16) -0.0167(15) C10 0.045(2) 0.0413(16) 0.048(2) 0.0090(16) -0.0185(18) -0.0198(16) C3' 0.043(2) 0.0435(16) 0.036(2) 0.0066(14) -0.0203(17) -0.0193(15) C4 0.0437(19) 0.0268(14) 0.039(2) 0.0018(14) -0.0197(17) -0.0145(14) C5' 0.058(2) 0.0506(19) 0.041(2) 0.0098(16) -0.0210(19) -0.0268(18) C1 0.047(2) 0.0292(15) 0.046(2) 0.0101(15) -0.0274(18) -0.0165(15) C13 0.055(2) 0.0593(19) 0.056(2) 0.0090(18) -0.033(2) -0.0225(18) C9 0.0396(19) 0.0301(14) 0.036(2) 0.0039(13) -0.0182(16) -0.0136(14) C9' 0.050(2) 0.0421(17) 0.043(2) 0.0067(16) -0.0256(19) -0.0247(17) C14 0.051(2) 0.0421(16) 0.053(2) 0.0081(16) -0.0257(19) -0.0214(16) C10' 0.065(2) 0.0455(18) 0.064(3) 0.0197(18) -0.033(2) -0.0274(18) C8' 0.058(2) 0.0498(18) 0.073(3) 0.0251(17) -0.040(2) -0.0236(17) C14' 0.066(3) 0.052(2) 0.051(3) 0.0036(19) -0.020(2) -0.026(2) C8 0.061(2) 0.0461(18) 0.044(2) 0.0096(16) -0.0145(19) -0.0193(17) C6 0.076(3) 0.0425(19) 0.072(3) -0.0103(18) -0.019(2) -0.0259(19) C7 0.088(3) 0.049(2) 0.114(4) 0.002(2) -0.044(3) -0.028(2) C13' 0.074(3) 0.075(2) 0.042(3) -0.005(2) -0.005(2) -0.035(2) C11' 0.094(3) 0.072(3) 0.070(3) 0.038(2) -0.033(3) -0.044(3) C6' 0.124(4) 0.080(3) 0.121(4) 0.022(3) -0.082(3) -0.064(3) C12' 0.106(4) 0.107(3) 0.053(3) 0.027(3) -0.024(3) -0.060(3) C7' 0.137(4) 0.080(3) 0.170(5) 0.022(3) -0.078(4) -0.070(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1' C1' 1.678(3) . ? S1 C1 1.679(3) . ? Cl1 C10 1.732(3) . ? Cl1' C10' 1.736(3) . ? C11 C12 1.365(4) . ? C11 C10 1.374(4) . ? C11 H11 0.9300 . ? O2 C5 1.340(3) . ? O2 C6 1.450(3) . ? O2' C5' 1.347(3) . ? O2' C6' 1.454(3) . ? N1 C1 1.355(3) . ? N1 C2 1.382(3) . ? N1 H1N 0.8600 . ? O1 C5 1.204(3) . ? O1' C5' 1.194(3) . ? N2' C1' 1.325(3) . ? N2' C4' 1.473(3) . ? N2' H2N' 0.8600 . ? N2 C1 1.325(3) . ? N2 C4 1.469(3) . ? N2 H2N 0.8600 . ? N1' C1' 1.351(3) . ? N1' C2' 1.395(3) . ? N1' H1N' 0.8600 . ? C2' C3' 1.346(3) . ? C2' C8' 1.497(3) . ? C4' C3' 1.517(3) . ? C4' C9' 1.517(4) . ? C4' H4' 0.9800 . ? C2 C3 1.344(3) . ? C2 C8 1.497(4) . ? C5 C3 1.472(4) . ? C12 C13 1.385(4) . ? C12 H12 0.9300 . ? C3 C4 1.513(4) . ? C10 C9 1.386(3) . ? C3' C5' 1.455(4) . ? C4 C9 1.530(3) . ? C4 H4 0.9800 . ? C13 C14 1.381(3) . ? C13 H13 0.9300 . ? C9 C14 1.382(4) . ? C9' C10' 1.381(4) . ? C9' C14' 1.383(4) . ? C14 H14 0.9300 . ? C10' C11' 1.375(5) . ? C8' H8'1 0.9600 . ? C8' H8'2 0.9600 . ? C8' H8'3 0.9600 . ? C14' C13' 1.382(4) . ? C14' H14' 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C6 C7 1.484(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C13' C12' 1.385(4) . ? C13' H13' 0.9300 . ? C11' C12' 1.359(5) . ? C11' H11' 0.9300 . ? C6' C7' 1.433(4) . ? C6' H6'1 0.9700 . ? C6' H6'2 0.9700 . ? C12' H12' 0.9300 . ? C7' H7'1 0.9600 . ? C7' H7'2 0.9600 . ? C7' H7'3 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 C11 C10 119.6(3) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C5 O2 C6 116.8(2) . . ? C5' O2' C6' 117.1(2) . . ? C1 N1 C2 124.9(2) . . ? C1 N1 H1N 117.5 . . ? C2 N1 H1N 117.5 . . ? C1' N2' C4' 127.9(2) . . ? C1' N2' H2N' 116.1 . . ? C4' N2' H2N' 116.1 . . ? C1 N2 C4 127.5(2) . . ? C1 N2 H2N 116.2 . . ? C4 N2 H2N 116.2 . . ? C1' N1' C2' 124.9(2) . . ? C1' N1' H1N' 117.5 . . ? C2' N1' H1N' 117.5 . . ? C3' C2' N1' 119.8(2) . . ? C3' C2' C8' 126.6(3) . . ? N1' C2' C8' 113.6(2) . . ? N2' C4' C3' 110.2(2) . . ? N2' C4' C9' 108.6(2) . . ? C3' C4' C9' 113.3(2) . . ? N2' C4' H4' 108.2 . . ? C3' C4' H4' 108.2 . . ? C9' C4' H4' 108.2 . . ? N2' C1' N1' 115.9(2) . . ? N2' C1' S1' 122.7(2) . . ? N1' C1' S1' 121.4(2) . . ? C3 C2 N1 119.7(3) . . ? C3 C2 C8 127.0(3) . . ? N1 C2 C8 113.3(2) . . ? O1 C5 O2 122.4(3) . . ? O1 C5 C3 127.1(3) . . ? O2 C5 C3 110.5(3) . . ? C11 C12 C13 121.0(3) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C2 C3 C5 121.6(3) . . ? C2 C3 C4 121.2(3) . . ? C5 C3 C4 116.9(2) . . ? C11 C10 C9 121.5(3) . . ? C11 C10 Cl1 117.5(2) . . ? C9 C10 Cl1 120.9(2) . . ? C2' C3' C5' 121.6(2) . . ? C2' C3' C4' 120.9(2) . . ? C5' C3' C4' 117.5(2) . . ? N2 C4 C3 110.1(2) . . ? N2 C4 C9 107.9(2) . . ? C3 C4 C9 112.8(2) . . ? N2 C4 H4 108.7 . . ? C3 C4 H4 108.7 . . ? C9 C4 H4 108.7 . . ? O1' C5' O2' 121.5(3) . . ? O1' C5' C3' 127.9(3) . . ? O2' C5' C3' 110.6(3) . . ? N2 C1 N1 116.0(2) . . ? N2 C1 S1 123.0(2) . . ? N1 C1 S1 121.1(2) . . ? C14 C13 C12 118.3(3) . . ? C14 C13 H13 120.9 . . ? C12 C13 H13 120.9 . . ? C14 C9 C10 117.4(2) . . ? C14 C9 C4 119.4(2) . . ? C10 C9 C4 123.2(2) . . ? C10' C9' C14' 116.9(3) . . ? C10' C9' C4' 122.9(3) . . ? C14' C9' C4' 120.2(3) . . ? C13 C14 C9 122.2(3) . . ? C13 C14 H14 118.9 . . ? C9 C14 H14 118.9 . . ? C11' C10' C9' 122.2(3) . . ? C11' C10' Cl1' 117.5(3) . . ? C9' C10' Cl1' 120.3(3) . . ? C2' C8' H8'1 109.5 . . ? C2' C8' H8'2 109.5 . . ? H8'1 C8' H8'2 109.5 . . ? C2' C8' H8'3 109.5 . . ? H8'1 C8' H8'3 109.5 . . ? H8'2 C8' H8'3 109.5 . . ? C13' C14' C9' 122.1(3) . . ? C13' C14' H14' 118.9 . . ? C9' C14' H14' 118.9 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C6 C7 107.1(3) . . ? O2 C6 H6A 110.3 . . ? C7 C6 H6A 110.3 . . ? O2 C6 H6B 110.3 . . ? C7 C6 H6B 110.3 . . ? H6A C6 H6B 108.6 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C14' C13' C12' 118.6(3) . . ? C14' C13' H13' 120.7 . . ? C12' C13' H13' 120.7 . . ? C12' C11' C10' 119.5(3) . . ? C12' C11' H11' 120.2 . . ? C10' C11' H11' 120.2 . . ? C7' C6' O2' 108.6(3) . . ? C7' C6' H6'1 110.0 . . ? O2' C6' H6'1 110.0 . . ? C7' C6' H6'2 110.0 . . ? O2' C6' H6'2 110.0 . . ? H6'1 C6' H6'2 108.3 . . ? C11' C12' C13' 120.7(4) . . ? C11' C12' H12' 119.6 . . ? C13' C12' H12' 119.6 . . ? C6' C7' H7'1 109.5 . . ? C6' C7' H7'2 109.5 . . ? H7'1 C7' H7'2 109.5 . . ? C6' C7' H7'3 109.5 . . ? H7'1 C7' H7'3 109.5 . . ? H7'2 C7' H7'3 109.5 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1' N1' C2' C3' -1.0(4) . . . . ? C1' N1' C2' C8' 179.7(3) . . . . ? C1' N2' C4' C3' -6.4(4) . . . . ? C1' N2' C4' C9' 118.2(3) . . . . ? C4' N2' C1' N1' 2.8(4) . . . . ? C4' N2' C1' S1' -178.3(2) . . . . ? C2' N1' C1' N2' 1.4(4) . . . . ? C2' N1' C1' S1' -177.5(2) . . . . ? C1 N1 C2 C3 4.3(4) . . . . ? C1 N1 C2 C8 -177.2(2) . . . . ? C6 O2 C5 O1 -5.9(4) . . . . ? C6 O2 C5 C3 175.0(2) . . . . ? C10 C11 C12 C13 -0.2(5) . . . . ? N1 C2 C3 C5 174.3(2) . . . . ? C8 C2 C3 C5 -4.0(4) . . . . ? N1 C2 C3 C4 0.9(4) . . . . ? C8 C2 C3 C4 -177.3(2) . . . . ? O1 C5 C3 C2 23.6(4) . . . . ? O2 C5 C3 C2 -157.4(2) . . . . ? O1 C5 C3 C4 -162.8(3) . . . . ? O2 C5 C3 C4 16.3(3) . . . . ? C12 C11 C10 C9 -0.1(5) . . . . ? C12 C11 C10 Cl1 -179.4(2) . . . . ? N1' C2' C3' C5' 175.3(3) . . . . ? C8' C2' C3' C5' -5.5(5) . . . . ? N1' C2' C3' C4' -3.4(4) . . . . ? C8' C2' C3' C4' 175.8(3) . . . . ? N2' C4' C3' C2' 6.4(4) . . . . ? C9' C4' C3' C2' -115.5(3) . . . . ? N2' C4' C3' C5' -172.4(2) . . . . ? C9' C4' C3' C5' 65.8(3) . . . . ? C1 N2 C4 C3 8.4(3) . . . . ? C1 N2 C4 C9 131.8(3) . . . . ? C2 C3 C4 N2 -6.3(3) . . . . ? C5 C3 C4 N2 -180.0(2) . . . . ? C2 C3 C4 C9 -126.9(3) . . . . ? C5 C3 C4 C9 59.5(3) . . . . ? C6' O2' C5' O1' -0.3(5) . . . . ? C6' O2' C5' C3' 178.8(3) . . . . ? C2' C3' C5' O1' 6.3(5) . . . . ? C4' C3' C5' O1' -174.9(3) . . . . ? C2' C3' C5' O2' -172.8(3) . . . . ? C4' C3' C5' O2' 6.0(4) . . . . ? C4 N2 C1 N1 -4.2(4) . . . . ? C4 N2 C1 S1 175.1(2) . . . . ? C2 N1 C1 N2 -2.8(4) . . . . ? C2 N1 C1 S1 177.9(2) . . . . ? C11 C12 C13 C14 -0.5(5) . . . . ? C11 C10 C9 C14 1.1(4) . . . . ? Cl1 C10 C9 C14 -179.6(2) . . . . ? C11 C10 C9 C4 -176.7(3) . . . . ? Cl1 C10 C9 C4 2.6(4) . . . . ? N2 C4 C9 C14 -74.5(3) . . . . ? C3 C4 C9 C14 47.4(3) . . . . ? N2 C4 C9 C10 103.3(3) . . . . ? C3 C4 C9 C10 -134.9(3) . . . . ? N2' C4' C9' C10' 96.0(3) . . . . ? C3' C4' C9' C10' -141.3(3) . . . . ? N2' C4' C9' C14' -81.8(3) . . . . ? C3' C4' C9' C14' 40.9(4) . . . . ? C12 C13 C14 C9 1.6(5) . . . . ? C10 C9 C14 C13 -1.8(4) . . . . ? C4 C9 C14 C13 176.0(3) . . . . ? C14' C9' C10' C11' 1.1(5) . . . . ? C4' C9' C10' C11' -176.8(3) . . . . ? C14' C9' C10' Cl1' -179.4(2) . . . . ? C4' C9' C10' Cl1' 2.7(4) . . . . ? C10' C9' C14' C13' -1.4(4) . . . . ? C4' C9' C14' C13' 176.5(3) . . . . ? C5 O2 C6 C7 155.6(3) . . . . ? C9' C14' C13' C12' 0.9(5) . . . . ? C9' C10' C11' C12' -0.1(6) . . . . ? Cl1' C10' C11' C12' -179.7(3) . . . . ? C5' O2' C6' C7' 163.6(3) . . . . ? C10' C11' C12' C13' -0.4(6) . . . . ? C14' C13' C12' C11' 0.1(6) . . . . ? #===END # Attachment 'PYR7.txt' # CIF-file generated for PYR7 in P2(1)/n #============================================================================== data_s3oc _database_code_depnum_ccdc_archive 'CCDC 734015' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 4-(3-Methoxy-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5- carboxylic acid ethyl ester ; _chemical_name_common ; 4-(3-Methoxy-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro- pyrimidine-5-carboxylic acid ethyl ester ; _chemical_melting_point ? _chemical_formula_moiety 'C15 H18 N2 O3 S' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C15 H18 N2 O3 S' _chemical_formula_iupac ? _chemical_formula_weight 306.38 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' N N 0.0061 0.0033 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 12.286(2) _cell_length_b 8.2534(10) _cell_length_c 15.956(3) _cell_angle_alpha 90 _cell_angle_beta 106.98(2) _cell_angle_gamma 90 _cell_volume 1547.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 400 _cell_measurement_theta_min 0.97 _cell_measurement_theta_max 27.99 _cell_special_details ; ; _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.18 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.220 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.9210 _exptl_absorpt_correction_T_max 0.9614 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Goniometer Xcalibur, detector: Eos (Nova)' _diffrn_detector_area_resol_mean 16.0839 _diffrn_orient_matrix_UB_11 0.0431520197 _diffrn_orient_matrix_UB_12 -0.0347641153 _diffrn_orient_matrix_UB_13 0.0351056656 _diffrn_orient_matrix_UB_21 0.0405448621 _diffrn_orient_matrix_UB_22 0.0148945011 _diffrn_orient_matrix_UB_23 -0.0229738866 _diffrn_orient_matrix_UB_31 0.0118915565 _diffrn_orient_matrix_UB_32 0.0773162309 _diffrn_orient_matrix_UB_33 0.0201818382 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -94.00 -59.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -17.1989 179.0000 60.0000 35 #__ type_ start__ end____ width___ exp.time_ 2 omega -32.00 68.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 0.0000 -90.0000 100 #__ type_ start__ end____ width___ exp.time_ 3 omega 1.00 86.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 37.0000 -60.0000 85 #__ type_ start__ end____ width___ exp.time_ 4 omega -90.00 9.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -17.1989 -37.0000 30.0000 99 #__ type_ start__ end____ width___ exp.time_ 5 omega -94.00 -34.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -17.1989 179.0000 150.0000 60 #__ type_ start__ end____ width___ exp.time_ 6 omega -32.00 19.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -17.1989 -89.0000 -23.0000 51 #__ type_ start__ end____ width___ exp.time_ 7 omega -94.00 -34.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -17.1989 179.0000 -60.0000 60 #__ type_ start__ end____ width___ exp.time_ 8 omega -17.00 32.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 89.0000 -156.0000 49 #__ type_ start__ end____ width___ exp.time_ 9 omega -53.00 46.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 -34.0000 122.0000 99 #__ type_ start__ end____ width___ exp.time_ 10 omega -87.00 -30.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -17.1989 -77.0000 -90.0000 57 #__ type_ start__ end____ width___ exp.time_ 11 omega -33.00 56.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 -89.0000 -23.0000 89 ; _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 22076 _diffrn_reflns_av_R_equivalents 0.0888 _diffrn_reflns_av_sigmaI/netI 0.0528 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 26.00 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 3032 # number of observed reflections (> n sig(I)) _reflns_number_gt 1858 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0661P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3032 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0886 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1297 _refine_ls_wR_factor_gt 0.1189 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.975 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.284 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.050 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 1.28992(5) 0.04196(7) 0.77187(5) 0.0529(2) Uani 1 1 d . . . N2 N 1.09765(15) 0.1837(2) 0.68659(12) 0.0395(5) Uani 1 1 d . . . H2N H 1.1364 0.2720 0.6926 0.047 Uiso 1 1 calc R . . O1 O 0.77733(15) -0.0499(2) 0.47672(11) 0.0579(5) Uani 1 1 d . . . N1 N 1.09409(15) -0.0903(2) 0.68102(12) 0.0438(5) Uani 1 1 d . . . H1N H 1.1212 -0.1810 0.7046 0.053 Uiso 1 1 calc R . . C1 C 1.15348(19) 0.0470(2) 0.71018(14) 0.0375(6) Uani 1 1 d . . . O2 O 0.78522(13) 0.21108(19) 0.51584(10) 0.0504(5) Uani 1 1 d . . . C4 C 0.97402(19) 0.1948(2) 0.65088(14) 0.0368(5) Uani 1 1 d . . . H4 H 0.9565 0.2902 0.6127 0.044 Uiso 1 1 calc R . . C3 C 0.93192(19) 0.0470(2) 0.59511(14) 0.0362(5) Uani 1 1 d . . . C9 C 0.92076(19) 0.2200(2) 0.72511(14) 0.0365(5) Uani 1 1 d . . . C5 C 0.8256(2) 0.0587(3) 0.52352(15) 0.0420(6) Uani 1 1 d . . . C14 C 0.8583(2) 0.1019(3) 0.75086(15) 0.0480(6) Uani 1 1 d . . . H14 H 0.8439 0.0038 0.7209 0.058 Uiso 1 1 calc R . . O3 O 0.91585(17) 0.5312(2) 0.88975(12) 0.0692(6) Uani 1 1 d . . . C10 C 0.94083(19) 0.3662(3) 0.77027(15) 0.0418(6) Uani 1 1 d . . . H10 H 0.9819 0.4472 0.7525 0.050 Uiso 1 1 calc R . . C2 C 0.99115(19) -0.0914(3) 0.61452(14) 0.0383(6) Uani 1 1 d . . . C6 C 0.6773(2) 0.2358(3) 0.44940(16) 0.0545(7) Uani 1 1 d . . . H6A H 0.6194 0.1664 0.4606 0.065 Uiso 1 1 calc R . . H6B H 0.6844 0.2100 0.3919 0.065 Uiso 1 1 calc R . . C11 C 0.9004(2) 0.3925(3) 0.84129(16) 0.0473(6) Uani 1 1 d . . . C8 C 0.9607(2) -0.2544(3) 0.57321(17) 0.0524(7) Uani 1 1 d . . . H8A H 0.9018 -0.2426 0.5187 0.079 Uiso 1 1 calc R . . H8B H 0.9341 -0.3227 0.6118 0.079 Uiso 1 1 calc R . . H8C H 1.0266 -0.3024 0.5626 0.079 Uiso 1 1 calc R . . C12 C 0.8374(2) 0.2731(3) 0.86663(17) 0.0558(7) Uani 1 1 d . . . H12 H 0.8092 0.2903 0.9140 0.067 Uiso 1 1 calc R . . C13 C 0.8168(2) 0.1297(3) 0.82179(17) 0.0564(7) Uani 1 1 d . . . H13 H 0.7744 0.0498 0.8390 0.068 Uiso 1 1 calc R . . C7 C 0.6454(2) 0.4095(4) 0.45304(19) 0.0734(9) Uani 1 1 d . . . H7A H 0.7047 0.4771 0.4442 0.110 Uiso 1 1 calc R . . H7B H 0.6353 0.4324 0.5093 0.110 Uiso 1 1 calc R . . H7C H 0.5757 0.4307 0.4080 0.110 Uiso 1 1 calc R . . C15 C 0.9806(3) 0.6581(4) 0.8670(2) 0.0838(10) Uani 1 1 d . . . H15A H 0.9440 0.6932 0.8082 0.126 Uiso 1 1 calc R . . H15B H 1.0556 0.6192 0.8711 0.126 Uiso 1 1 calc R . . H15C H 0.9859 0.7475 0.9065 0.126 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0380(4) 0.0355(4) 0.0749(5) -0.0063(3) 0.0004(3) 0.0025(3) N2 0.0324(11) 0.0289(10) 0.0539(12) -0.0028(9) 0.0076(10) -0.0029(8) O1 0.0564(12) 0.0564(12) 0.0500(10) -0.0132(9) -0.0017(9) -0.0027(9) N1 0.0410(12) 0.0281(10) 0.0557(12) 0.0002(9) 0.0036(10) 0.0003(9) C1 0.0402(14) 0.0296(12) 0.0421(13) -0.0026(10) 0.0110(11) -0.0006(11) O2 0.0439(11) 0.0476(10) 0.0481(10) 0.0001(8) -0.0045(8) 0.0058(8) C4 0.0363(13) 0.0311(12) 0.0379(13) 0.0026(10) 0.0029(10) 0.0026(10) C3 0.0398(14) 0.0320(12) 0.0346(12) -0.0010(10) 0.0072(10) -0.0020(10) C9 0.0323(13) 0.0363(13) 0.0359(12) 0.0013(10) 0.0021(10) 0.0039(10) C5 0.0427(15) 0.0473(15) 0.0362(13) 0.0014(12) 0.0121(11) -0.0015(12) C14 0.0451(15) 0.0483(14) 0.0490(15) -0.0047(12) 0.0114(12) -0.0056(12) O3 0.0795(15) 0.0634(13) 0.0689(13) -0.0253(10) 0.0282(11) 0.0010(11) C10 0.0399(14) 0.0360(13) 0.0475(14) -0.0017(11) 0.0097(11) 0.0014(11) C2 0.0382(14) 0.0376(13) 0.0374(13) -0.0048(11) 0.0085(11) -0.0055(11) C6 0.0446(16) 0.0657(18) 0.0436(15) 0.0047(13) -0.0024(12) 0.0066(13) C11 0.0448(15) 0.0474(15) 0.0456(15) -0.0078(12) 0.0068(12) 0.0079(12) C8 0.0530(17) 0.0388(14) 0.0600(16) -0.0096(12) 0.0081(13) -0.0022(12) C12 0.0494(17) 0.0720(19) 0.0484(15) -0.0035(14) 0.0179(13) 0.0077(14) C13 0.0527(18) 0.0645(18) 0.0537(16) -0.0009(14) 0.0183(14) -0.0103(14) C7 0.066(2) 0.076(2) 0.0657(19) 0.0011(16) 0.0005(16) 0.0213(16) C15 0.107(3) 0.0550(18) 0.094(2) -0.0320(17) 0.036(2) -0.0123(18) #=============================================================================== _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.678(2) . ? N2 C1 1.318(3) . ? N2 C4 1.461(3) . ? N2 H2N 0.8600 . ? O1 C5 1.206(3) . ? N1 C1 1.354(3) . ? N1 C2 1.393(3) . ? N1 H1N 0.8600 . ? O2 C5 1.345(3) . ? O2 C6 1.450(3) . ? C4 C3 1.510(3) . ? C4 C9 1.525(3) . ? C4 H4 0.9800 . ? C3 C2 1.341(3) . ? C3 C5 1.466(3) . ? C9 C14 1.376(3) . ? C9 C10 1.390(3) . ? C14 C13 1.390(3) . ? C14 H14 0.9300 . ? O3 C11 1.363(3) . ? O3 C15 1.425(3) . ? C10 C11 1.381(3) . ? C10 H10 0.9300 . ? C2 C8 1.497(3) . ? C6 C7 1.491(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C11 C12 1.385(3) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C12 C13 1.368(4) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N2 C4 124.07(18) . . ? C1 N2 H2N 118.0 . . ? C4 N2 H2N 118.0 . . ? C1 N1 C2 123.06(19) . . ? C1 N1 H1N 118.5 . . ? C2 N1 H1N 118.5 . . ? N2 C1 N1 115.8(2) . . ? N2 C1 S1 122.41(16) . . ? N1 C1 S1 121.78(17) . . ? C5 O2 C6 115.65(18) . . ? N2 C4 C3 108.51(17) . . ? N2 C4 C9 109.79(17) . . ? C3 C4 C9 114.65(19) . . ? N2 C4 H4 107.9 . . ? C3 C4 H4 107.9 . . ? C9 C4 H4 107.9 . . ? C2 C3 C5 122.4(2) . . ? C2 C3 C4 118.9(2) . . ? C5 C3 C4 118.70(19) . . ? C14 C9 C10 119.4(2) . . ? C14 C9 C4 122.57(19) . . ? C10 C9 C4 118.00(19) . . ? O1 C5 O2 122.5(2) . . ? O1 C5 C3 126.8(2) . . ? O2 C5 C3 110.71(19) . . ? C9 C14 C13 119.7(2) . . ? C9 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C11 O3 C15 117.9(2) . . ? C11 C10 C9 120.7(2) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C3 C2 N1 118.73(19) . . ? C3 C2 C8 127.9(2) . . ? N1 C2 C8 113.3(2) . . ? O2 C6 C7 107.6(2) . . ? O2 C6 H6A 110.2 . . ? C7 C6 H6A 110.2 . . ? O2 C6 H6B 110.2 . . ? C7 C6 H6B 110.2 . . ? H6A C6 H6B 108.5 . . ? O3 C11 C10 125.0(2) . . ? O3 C11 C12 115.4(2) . . ? C10 C11 C12 119.6(2) . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C13 C12 C11 119.8(2) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 120.9(2) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O3 C15 H15A 109.5 . . ? O3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N2 C1 N1 15.1(3) . . . . ? C4 N2 C1 S1 -165.33(16) . . . . ? C2 N1 C1 N2 14.6(3) . . . . ? C2 N1 C1 S1 -164.98(17) . . . . ? C1 N2 C4 C3 -35.2(3) . . . . ? C1 N2 C4 C9 90.8(2) . . . . ? N2 C4 C3 C2 28.6(3) . . . . ? C9 C4 C3 C2 -94.5(3) . . . . ? N2 C4 C3 C5 -153.41(19) . . . . ? C9 C4 C3 C5 83.5(2) . . . . ? N2 C4 C9 C14 -109.4(2) . . . . ? C3 C4 C9 C14 13.0(3) . . . . ? N2 C4 C9 C10 67.8(2) . . . . ? C3 C4 C9 C10 -169.74(19) . . . . ? C6 O2 C5 O1 2.0(3) . . . . ? C6 O2 C5 C3 -177.39(18) . . . . ? C2 C3 C5 O1 2.7(4) . . . . ? C4 C3 C5 O1 -175.2(2) . . . . ? C2 C3 C5 O2 -178.0(2) . . . . ? C4 C3 C5 O2 4.2(3) . . . . ? C10 C9 C14 C13 -0.4(3) . . . . ? C4 C9 C14 C13 176.8(2) . . . . ? C14 C9 C10 C11 1.1(3) . . . . ? C4 C9 C10 C11 -176.2(2) . . . . ? C5 C3 C2 N1 177.1(2) . . . . ? C4 C3 C2 N1 -5.1(3) . . . . ? C5 C3 C2 C8 -3.2(4) . . . . ? C4 C3 C2 C8 174.7(2) . . . . ? C1 N1 C2 C3 -19.3(3) . . . . ? C1 N1 C2 C8 160.9(2) . . . . ? C5 O2 C6 C7 178.2(2) . . . . ? C15 O3 C11 C10 -1.4(4) . . . . ? C15 O3 C11 C12 179.6(2) . . . . ? C9 C10 C11 O3 179.9(2) . . . . ? C9 C10 C11 C12 -1.3(3) . . . . ? O3 C11 C12 C13 179.7(2) . . . . ? C10 C11 C12 C13 0.7(4) . . . . ? C11 C12 C13 C14 0.0(4) . . . . ? C9 C14 C13 C12 -0.2(4) . . . . ? #===END # Attachment 'PYR5.txt' data_PYR5 _database_code_depnum_ccdc_archive 'CCDC 738484' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H21 N3 O2 S' _chemical_formula_sum 'C16 H21 N3 O2 S' _chemical_formula_weight 319.42 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.369(3) _cell_length_b 9.4420(19) _cell_length_c 13.086(3) _cell_angle_alpha 102.79(3) _cell_angle_beta 90.557(19) _cell_angle_gamma 110.68(2) _cell_volume 826.8(5) _cell_formula_units_Z 2 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 550 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 26.4 _exptl_crystal_description plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.206 _exptl_absorpt_correction_type 'multi-scan ' # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'SADABS, 1996' _exptl_absorpt_correction_T_min 0.9307 _exptl_absorpt_correction_T_max 0.9797 _exptl_special_details ; ? ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 4460 _diffrn_reflns_av_R_equivalents 0.0121 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 33.84 _reflns_number_total 3070 _reflns_number_gt 2435 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.2934P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3070 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1130 _refine_ls_wR_factor_gt 0.1031 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C8 C 0.8269(2) 0.5786(2) 0.3464(2) 0.0479(8) Uani 1 1 d . A 1 H8A H 0.8441 0.5715 0.2730 0.072 Uiso 1 1 calc R A 1 H8B H 0.9490 0.5989 0.3844 0.072 Uiso 1 1 calc R A 1 H8C H 0.7814 0.6620 0.3732 0.072 Uiso 1 1 calc R A 1 S1 S 0.80073(6) 0.10239(5) 0.45983(5) 0.0420(2) Uani 1 1 d . A 1 O2 O 0.46834(17) 0.59573(15) 0.29523(14) 0.0477(5) Uani 1 1 d . A 1 O1 O 0.20535(17) 0.45301(16) 0.35985(14) 0.0515(5) Uani 1 1 d . A 1 N2 N 0.48407(18) 0.16561(16) 0.42500(15) 0.0338(5) Uani 1 1 d . A 1 H2N H 0.4281 0.1052 0.4650 0.041 Uiso 1 1 calc R A 1 N1 N 0.76654(18) 0.32549(16) 0.37882(15) 0.0344(5) Uani 1 1 d . A 1 H1N H 0.8849 0.3423 0.3646 0.041 Uiso 1 1 calc R A 1 C2 C 0.6809(2) 0.42867(18) 0.35956(18) 0.0301(6) Uani 1 1 d . A 1 C4 C 0.3629(2) 0.22351(18) 0.36828(17) 0.0298(6) Uani 1 1 d . A 1 H4 H 0.2567 0.2317 0.4108 0.036 Uiso 1 1 calc R A 1 C3 C 0.4850(2) 0.38507(18) 0.35721(18) 0.0299(6) Uani 1 1 d . A 1 C1 C 0.6740(2) 0.20005(18) 0.41876(18) 0.0295(6) Uani 1 1 d . A 1 N3 N 0.0310(3) -0.2300(2) -0.0199(2) 0.0633(8) Uani 1 1 d . A 1 C5 C 0.3725(2) 0.48056(19) 0.33962(18) 0.0343(6) Uani 1 1 d . A 1 C6 C 0.3726(3) 0.6993(2) 0.2755(2) 0.0444(7) Uani 1 1 d . A 1 H6A H 0.3622 0.7663 0.3412 0.053 Uiso 1 1 calc R A 1 H6B H 0.2427 0.6393 0.2405 0.053 Uiso 1 1 calc R A 1 C13 C 0.2682(3) 0.0198(2) 0.0750(2) 0.0438(7) Uani 1 1 d . A 1 H13 H 0.3218 0.0376 0.0129 0.053 Uiso 1 1 calc R A 1 C10 C 0.1137(2) -0.0267(2) 0.2610(2) 0.0377(6) Uani 1 1 d . A 1 H10 H 0.0599 -0.0433 0.3233 0.045 Uiso 1 1 calc R A 1 C14 C 0.3460(3) 0.1292(2) 0.1693(2) 0.0378(7) Uani 1 1 d . A 1 H14 H 0.4513 0.2195 0.1687 0.045 Uiso 1 1 calc R A 1 C9 C 0.2737(2) 0.10971(18) 0.26366(19) 0.0278(6) Uani 1 1 d . A 1 C12 C 0.1084(3) -0.1180(2) 0.0728(2) 0.0422(8) Uani 1 1 d . A 1 C11 C 0.0339(3) -0.1372(2) 0.1680(2) 0.0431(8) Uani 1 1 d . A 1 H11 H -0.0724 -0.2266 0.1691 0.052 Uiso 1 1 calc R A 1 C7 C 0.4940(3) 0.7935(3) 0.2075(2) 0.0604(9) Uani 1 1 d . A 1 H7A H 0.6224 0.8514 0.2428 0.091 Uiso 1 1 calc R A 1 H7B H 0.4363 0.8646 0.1932 0.091 Uiso 1 1 calc R A 1 H7C H 0.5020 0.7259 0.1426 0.091 Uiso 1 1 calc R A 1 C15 C -0.1492(4) -0.3597(3) -0.0223(3) 0.0857(11) Uani 1 1 d . A 1 H15A H -0.1274 -0.4271 0.0176 0.129 Uiso 1 1 calc R A 1 H15B H -0.1939 -0.4170 -0.0939 0.129 Uiso 1 1 calc R A 1 H15C H -0.2459 -0.3209 0.0077 0.129 Uiso 1 1 calc R A 1 C16 C 0.1062(4) -0.2094(4) -0.1174(3) 0.0749(11) Uani 1 1 d . A 1 H16A H 0.0960 -0.1169 -0.1316 0.112 Uiso 1 1 calc R A 1 H16B H 0.0329 -0.2981 -0.1727 0.112 Uiso 1 1 calc R A 1 H16C H 0.2405 -0.1994 -0.1136 0.112 Uiso 1 1 calc R A 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C8 0.0278(7) 0.0375(9) 0.079(2) 0.0255(11) 0.0064(9) 0.0062(6) S1 0.0313(2) 0.0435(2) 0.0586(7) 0.0236(3) 0.0046(2) 0.01562(17) O2 0.0350(6) 0.0460(7) 0.0775(16) 0.0334(8) 0.0145(7) 0.0220(5) O1 0.0295(5) 0.0530(8) 0.0828(17) 0.0295(8) 0.0148(7) 0.0198(5) N2 0.0251(6) 0.0389(7) 0.0397(17) 0.0213(8) 0.0046(7) 0.0072(5) N1 0.0237(5) 0.0379(7) 0.0467(17) 0.0192(8) 0.0088(7) 0.0120(5) C2 0.0257(6) 0.0295(7) 0.0348(19) 0.0099(8) 0.0032(8) 0.0084(5) C4 0.0219(6) 0.0325(8) 0.0368(19) 0.0134(9) 0.0048(7) 0.0089(5) C3 0.0246(6) 0.0307(7) 0.035(2) 0.0099(8) 0.0034(8) 0.0094(6) C1 0.0275(6) 0.0327(8) 0.0276(19) 0.0087(8) 0.0020(8) 0.0091(6) N3 0.0670(13) 0.0672(13) 0.036(3) -0.0077(12) -0.0028(13) 0.0136(10) C5 0.0275(7) 0.0321(8) 0.043(2) 0.0077(9) 0.0018(8) 0.0109(6) C6 0.0419(9) 0.0408(9) 0.061(2) 0.0164(10) 0.0074(10) 0.0254(8) C13 0.0447(10) 0.0542(12) 0.036(2) 0.0146(12) 0.0098(10) 0.0198(9) C10 0.0316(7) 0.0405(9) 0.039(2) 0.0142(10) 0.0063(9) 0.0076(7) C14 0.0331(8) 0.0397(9) 0.039(2) 0.0117(11) 0.0046(10) 0.0106(7) C9 0.0249(6) 0.0330(8) 0.028(2) 0.0115(9) 0.0041(8) 0.0108(6) C12 0.0413(9) 0.0470(11) 0.037(3) 0.0036(12) -0.0027(12) 0.0192(8) C11 0.0359(8) 0.0378(9) 0.046(3) 0.0060(11) 0.0000(11) 0.0049(7) C7 0.0535(12) 0.0567(12) 0.089(3) 0.0381(14) 0.0159(13) 0.0291(10) C15 0.0806(18) 0.0638(16) 0.077(3) -0.0163(16) -0.0115(17) 0.0035(14) C16 0.0704(16) 0.098(2) 0.048(3) -0.0106(18) -0.0018(17) 0.0380(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C8 C2 1.493(2) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? S1 C1 1.6820(17) . ? O2 C5 1.328(2) . ? O2 C6 1.455(2) . ? O1 C5 1.211(2) . ? N2 C1 1.328(2) . ? N2 C4 1.469(2) . ? N2 H2N 0.8600 . ? N1 C1 1.361(2) . ? N1 C2 1.397(2) . ? N1 H1N 0.8600 . ? C2 C3 1.352(2) . ? C4 C3 1.513(2) . ? C4 C9 1.514(3) . ? C4 H4 0.9800 . ? C3 C5 1.472(2) . ? N3 C12 1.382(3) . ? N3 C16 1.421(4) . ? N3 C15 1.448(4) . ? C6 C7 1.478(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C13 C14 1.387(3) . ? C13 C12 1.407(3) . ? C13 H13 0.9300 . ? C10 C11 1.380(3) . ? C10 C9 1.399(2) . ? C10 H10 0.9300 . ? C14 C9 1.373(3) . ? C14 H14 0.9300 . ? C12 C11 1.389(3) . ? C11 H11 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O2 C6 118.73(14) . . ? C1 N2 C4 124.54(16) . . ? C1 N2 H2N 117.7 . . ? C4 N2 H2N 117.7 . . ? C1 N1 C2 123.96(13) . . ? C1 N1 H1N 118.0 . . ? C2 N1 H1N 118.0 . . ? C3 C2 N1 118.55(14) . . ? C3 C2 C8 128.64(15) . . ? N1 C2 C8 112.79(13) . . ? N2 C4 C3 108.88(12) . . ? N2 C4 C9 110.42(13) . . ? C3 C4 C9 113.07(18) . . ? N2 C4 H4 108.1 . . ? C3 C4 H4 108.1 . . ? C9 C4 H4 108.1 . . ? C2 C3 C5 125.38(15) . . ? C2 C3 C4 119.85(14) . . ? C5 C3 C4 114.72(13) . . ? N2 C1 N1 115.75(15) . . ? N2 C1 S1 124.02(14) . . ? N1 C1 S1 120.20(12) . . ? C12 N3 C16 121.5(2) . . ? C12 N3 C15 119.9(3) . . ? C16 N3 C15 117.9(2) . . ? O1 C5 O2 122.94(15) . . ? O1 C5 C3 123.14(17) . . ? O2 C5 C3 113.86(14) . . ? O2 C6 C7 106.81(15) . . ? O2 C6 H6A 110.4 . . ? C7 C6 H6A 110.4 . . ? O2 C6 H6B 110.4 . . ? C7 C6 H6B 110.4 . . ? H6A C6 H6B 108.6 . . ? C14 C13 C12 120.3(2) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C11 C10 C9 121.5(2) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C9 C14 C13 122.64(19) . . ? C9 C14 H14 118.7 . . ? C13 C14 H14 118.7 . . ? C14 C9 C10 116.86(19) . . ? C14 C9 C4 123.51(16) . . ? C10 C9 C4 119.6(2) . . ? N3 C12 C11 121.6(2) . . ? N3 C12 C13 121.3(3) . . ? C11 C12 C13 117.1(2) . . ? C10 C11 C12 121.59(19) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 C2 C3 -15.6(3) . . . . ? C1 N1 C2 C8 163.1(2) . . . . ? C1 N2 C4 C3 -32.6(3) . . . . ? C1 N2 C4 C9 92.1(2) . . . . ? N1 C2 C3 C5 179.01(19) . . . . ? C8 C2 C3 C5 0.5(4) . . . . ? N1 C2 C3 C4 -3.9(3) . . . . ? C8 C2 C3 C4 177.6(2) . . . . ? N2 C4 C3 C2 24.7(3) . . . . ? C9 C4 C3 C2 -98.4(2) . . . . ? N2 C4 C3 C5 -157.92(18) . . . . ? C9 C4 C3 C5 78.9(2) . . . . ? C4 N2 C1 N1 16.9(3) . . . . ? C4 N2 C1 S1 -164.92(15) . . . . ? C2 N1 C1 N2 9.5(3) . . . . ? C2 N1 C1 S1 -168.73(16) . . . . ? C6 O2 C5 O1 3.7(3) . . . . ? C6 O2 C5 C3 -179.10(18) . . . . ? C2 C3 C5 O1 -163.8(2) . . . . ? C4 C3 C5 O1 19.0(3) . . . . ? C2 C3 C5 O2 19.0(3) . . . . ? C4 C3 C5 O2 -158.19(19) . . . . ? C5 O2 C6 C7 -168.8(2) . . . . ? C12 C13 C14 C9 0.2(3) . . . . ? C13 C14 C9 C10 -0.8(3) . . . . ? C13 C14 C9 C4 176.66(16) . . . . ? C11 C10 C9 C14 0.7(2) . . . . ? C11 C10 C9 C4 -176.80(16) . . . . ? N2 C4 C9 C14 -100.28(18) . . . . ? C3 C4 C9 C14 22.0(2) . . . . ? N2 C4 C9 C10 77.10(18) . . . . ? C3 C4 C9 C10 -160.63(14) . . . . ? C16 N3 C12 C11 179.3(2) . . . . ? C15 N3 C12 C11 9.4(3) . . . . ? C16 N3 C12 C13 -1.5(3) . . . . ? C15 N3 C12 C13 -171.4(2) . . . . ? C14 C13 C12 N3 -178.72(19) . . . . ? C14 C13 C12 C11 0.5(3) . . . . ? C9 C10 C11 C12 -0.1(3) . . . . ? N3 C12 C11 C10 178.69(19) . . . . ? C13 C12 C11 C10 -0.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.287 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.041