# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author 'Martins, Felipe Terra' _publ_contact_author_email felipetmartins@yahoo.com.br loop_ _publ_author_name 'C.da Silva' R.Coelho M.Cirqueira 'A.de Melo' I.Landre J.Ellena F.Martins data_LamPhthalate_298K _database_code_depnum_ccdc_archive 'CCDC 871607' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-(1H)-pyrimidin-2-one hydrogen phthalate ; _chemical_formula_moiety 'C8 H12 N3 O3 S, C8 H5 O4' _chemical_formula_sum 'C16 H17 N3 O7 S' _chemical_name_common 'lamivudine hydrogen phthalate' _chemical_compound_source 'Crystal Screening' _chemical_formula_weight 395.39 _chemical_absolute_configuration rmad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.39900(10) _cell_length_b 15.7550(4) _cell_length_c 20.6980(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1760.60(7) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2065 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 26.373 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.251 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_min 0.078 _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.23 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_unetI/netI 0.0402 _diffrn_reflns_number 7211 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 26.36 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _reflns_number_total 3530 _reflns_number_gt 2810 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.0687P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3530 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.1042 _refine_ls_wR_factor_gt 0.0958 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(8) _refine_diff_density_max 0.135 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.034 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 S3' S -0.05305(11) 1.00690(4) 0.40189(3) 0.05872(19) Uani 1 1 d . . . O1' O 0.3864(3) 0.93790(9) 0.42360(8) 0.0533(4) Uani 1 1 d . . . N1 N 0.1901(3) 0.80555(10) 0.40364(8) 0.0448(4) Uani 1 1 d . . . O2 O 0.5404(3) 0.74806(9) 0.44810(7) 0.0565(4) Uani 1 1 d . . . O5' O 0.2531(4) 1.08164(11) 0.29054(9) 0.0733(6) Uani 1 1 d . . . C2 C 0.3675(4) 0.74227(13) 0.41032(10) 0.0458(5) Uani 1 1 d . . . N3 N 0.3373(4) 0.67186(11) 0.37185(9) 0.0517(5) Uani 1 1 d . . . O1XB O 0.6573(4) 0.54068(10) 0.39238(9) 0.0705(5) Uani 1 1 d . . . C6 C 0.0078(4) 0.79813(14) 0.35751(10) 0.0509(5) Uani 1 1 d . . . H6 H -0.1054 0.8422 0.3528 0.061 Uiso 1 1 calc R . . C2B C 0.7976(5) 0.39854(13) 0.38767(10) 0.0515(5) Uani 1 1 d . . . C4 C 0.1544(4) 0.66178(14) 0.32757(10) 0.0495(5) Uani 1 1 d . . . C4' C 0.2823(4) 1.00862(13) 0.39103(10) 0.0484(5) Uani 1 1 d . . . H4' H 0.3479 1.0607 0.4104 0.058 Uiso 1 1 calc R . . C1' C 0.2122(4) 0.87856(12) 0.44771(10) 0.0452(5) Uani 1 1 d . . . H1' H 0.2754 0.8573 0.489 0.054 Uiso 1 1 calc R . . N4 N 0.1416(5) 0.59071(13) 0.29507(10) 0.0612(5) Uani 1 1 d . . . O1YB O 0.4778(4) 0.45843(11) 0.32012(9) 0.0773(6) Uani 1 1 d . . . C1B C 0.6352(5) 0.47054(14) 0.36547(11) 0.0555(6) Uani 1 1 d . . . O4YB O 0.4697(5) 0.31477(13) 0.28412(10) 0.0870(6) Uani 1 1 d . . . C5 C -0.0133(5) 0.72999(13) 0.31909(10) 0.0544(5) Uani 1 1 d . . . H5 H -0.1356 0.7276 0.2875 0.065 Uiso 1 1 calc R . . C4B C 0.6068(5) 0.27052(17) 0.32232(14) 0.0676(7) Uani 1 1 d . . . C2' C -0.0291(4) 0.92345(13) 0.46102(10) 0.0517(5) Uani 1 1 d . . . H2'1 H -0.0295 0.9469 0.5043 0.062 Uiso 1 1 calc R . . H2'2 H -0.167 0.8844 0.457 0.062 Uiso 1 1 calc R . . C3B C 0.7869(5) 0.31244(14) 0.36850(11) 0.0541(5) Uani 1 1 d . . . C8B C 0.9781(5) 0.42112(15) 0.43263(12) 0.0636(6) Uani 1 1 d . . . H8B H 0.9874 0.4774 0.446 0.076 Uiso 1 1 calc R . . C6B C 1.1339(6) 0.28033(18) 0.43852(14) 0.0754(8) Uani 1 1 d . . . H6B H 1.2461 0.2409 0.4547 0.09 Uiso 1 1 calc R . . C5' C 0.3469(5) 1.00782(15) 0.32051(11) 0.0581(6) Uani 1 1 d . . . H5'1 H 0.5254 1.0056 0.3154 0.07 Uiso 1 1 calc R . . H5'2 H 0.2766 0.9578 0.3002 0.07 Uiso 1 1 calc R . . O4XB O 0.5976(5) 0.19332(12) 0.32045(13) 0.1021(8) Uani 1 1 d . . . C7B C 1.1431(5) 0.36344(17) 0.45805(13) 0.0707(7) Uani 1 1 d . . . H7B H 1.2601 0.3807 0.4883 0.085 Uiso 1 1 calc R . . C5B C 0.9569(6) 0.25623(16) 0.39475(13) 0.0692(7) Uani 1 1 d . . . H5B H 0.9506 0.1996 0.3821 0.083 Uiso 1 1 calc R . . H4OM H 0.488(7) 0.386(2) 0.2985(15) 0.104 Uiso 1 1 d . . . H4NY H 0.030(7) 0.5848(16) 0.2670(15) 0.083 Uiso 1 1 d . . . H3 H 0.443(7) 0.6301(19) 0.3772(14) 0.083 Uiso 1 1 d . . . H4NX H 0.251(7) 0.5503(17) 0.3048(14) 0.083 Uiso 1 1 d . . . H5'O H 0.335(7) 1.124(2) 0.2990(17) 0.104 Uiso 1 1 d . . . 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 S3' 0.0477(3) 0.0559(3) 0.0725(4) 0.0061(3) -0.0057(3) 0.0095(3) O1' 0.0425(8) 0.0484(8) 0.0691(9) 0.0160(7) -0.0050(8) -0.0007(6) N1 0.0427(9) 0.0440(8) 0.0476(9) 0.0006(7) -0.0086(8) 0.0034(7) O2 0.0512(9) 0.0572(8) 0.0611(8) -0.0018(7) -0.0170(8) 0.0054(8) O5' 0.0747(13) 0.0724(12) 0.0728(11) 0.0264(9) -0.0294(10) -0.0141(10) C2 0.0422(11) 0.0487(11) 0.0463(10) 0.0025(9) -0.0047(10) 0.0000(8) N3 0.0508(11) 0.0501(10) 0.0540(10) -0.0030(8) -0.0101(9) 0.0071(8) O1XB 0.0811(13) 0.0561(9) 0.0742(11) -0.0114(8) -0.0051(10) 0.0184(9) C6 0.0452(12) 0.0546(12) 0.0529(11) 0.0047(9) -0.0097(11) 0.0024(10) C2B 0.0543(13) 0.0493(11) 0.0508(11) -0.0030(9) 0.0088(10) 0.0035(10) C4 0.0496(12) 0.0559(12) 0.0431(10) -0.0007(9) -0.0037(10) -0.0024(10) C4' 0.0516(12) 0.0397(10) 0.0539(11) 0.0056(9) -0.0118(10) -0.0026(9) C1' 0.0418(11) 0.0479(11) 0.0459(10) 0.0036(8) -0.0038(9) -0.0048(9) N4 0.0627(14) 0.0607(12) 0.0602(12) -0.0097(10) -0.0126(10) 0.0027(10) O1YB 0.0951(16) 0.0675(11) 0.0692(10) -0.0059(9) -0.0223(12) 0.0158(11) C1B 0.0613(15) 0.0542(13) 0.0511(12) 0.0006(10) 0.0102(12) 0.0053(10) O4YB 0.0940(16) 0.0758(12) 0.0912(13) -0.0185(10) -0.0288(13) -0.0016(12) C5 0.0514(13) 0.0586(12) 0.0533(11) -0.0036(10) -0.0136(11) 0.0022(10) C4B 0.0630(16) 0.0610(15) 0.0789(16) -0.0152(13) 0.0013(14) 0.0016(12) C2' 0.0462(12) 0.0555(12) 0.0534(11) -0.0020(9) -0.0004(10) 0.0026(10) C3B 0.0530(13) 0.0506(12) 0.0586(12) -0.0058(10) 0.0082(11) -0.0017(10) C8B 0.0683(16) 0.0572(13) 0.0653(14) -0.0128(11) -0.0033(13) 0.0008(12) C6B 0.0711(18) 0.0706(17) 0.0845(18) 0.0041(14) -0.0098(16) 0.0120(14) C5' 0.0540(14) 0.0636(13) 0.0565(12) 0.0092(10) -0.0076(11) -0.0016(11) O4XB 0.0979(18) 0.0569(11) 0.151(2) -0.0215(12) -0.0216(16) -0.0102(11) C7B 0.0692(18) 0.0695(15) 0.0734(16) -0.0063(13) -0.0105(14) 0.0108(13) C5B 0.0741(17) 0.0493(12) 0.0841(17) -0.0038(12) 0.0051(15) 0.0066(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 S3' C2' 1.801(2) . ? S3' C4' 1.824(2) . ? O1' C1' 1.417(2) . ? O1' C4' 1.418(2) . ? N1 C6 1.376(3) . ? N1 C2 1.390(3) . ? N1 C1' 1.473(2) . ? O2 C2 1.221(2) . ? O5' C5' 1.412(3) . ? O5' H5'O 0.82(3) . ? C2 N3 1.375(3) . ? N3 C4 1.357(3) . ? N3 H3 0.88(3) . ? O1XB C1B 1.243(3) . ? C6 C5 1.341(3) . ? C6 H6 0.93 . ? C2B C8B 1.394(4) . ? C2B C3B 1.414(3) . ? C2B C1B 1.505(3) . ? C4 N4 1.308(3) . ? C4 C5 1.416(3) . ? C4' C5' 1.501(3) . ? C4' H4' 0.98 . ? C1' C2' 1.508(3) . ? C1' H1' 0.98 . ? N4 H4NY 0.84(3) . ? N4 H4NX 0.89(3) . ? O1YB C1B 1.281(3) . ? O1YB H4OM 1.22(3) . ? O4YB C4B 1.288(3) . ? O4YB H4OM 1.17(3) . ? C5 H5 0.93 . ? C4B O4XB 1.218(3) . ? C4B C3B 1.515(4) . ? C2' H2'1 0.97 . ? C2' H2'2 0.97 . ? C3B C5B 1.386(4) . ? C8B C7B 1.377(4) . ? C8B H8B 0.93 . ? C6B C5B 1.370(4) . ? C6B C7B 1.371(4) . ? C6B H6B 0.93 . ? C5' H5'1 0.97 . ? C5' H5'2 0.97 . ? C7B H7B 0.93 . ? C5B H5B 0.93 . ? 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 C2' S3' C4' 91.33(10) . . ? C1' O1' C4' 115.00(17) . . ? C6 N1 C2 120.08(17) . . ? C6 N1 C1' 123.64(17) . . ? C2 N1 C1' 116.28(16) . . ? C5' O5' H5'O 112(3) . . ? O2 C2 N3 121.45(19) . . ? O2 C2 N1 122.49(19) . . ? N3 C2 N1 116.07(18) . . ? C4 N3 C2 124.88(19) . . ? C4 N3 H3 118(2) . . ? C2 N3 H3 117(2) . . ? C5 C6 N1 122.7(2) . . ? C5 C6 H6 118.7 . . ? N1 C6 H6 118.7 . . ? C8B C2B C3B 117.4(2) . . ? C8B C2B C1B 114.75(19) . . ? C3B C2B C1B 127.8(2) . . ? N4 C4 N3 119.1(2) . . ? N4 C4 C5 123.5(2) . . ? N3 C4 C5 117.41(18) . . ? O1' C4' C5' 111.31(19) . . ? O1' C4' S3' 108.85(14) . . ? C5' C4' S3' 110.51(16) . . ? O1' C4' H4' 108.7 . . ? C5' C4' H4' 108.7 . . ? S3' C4' H4' 108.7 . . ? O1' C1' N1 110.56(17) . . ? O1' C1' C2' 109.17(16) . . ? N1 C1' C2' 114.17(18) . . ? O1' C1' H1' 107.6 . . ? N1 C1' H1' 107.6 . . ? C2' C1' H1' 107.6 . . ? C4 N4 H4NY 119.1(19) . . ? C4 N4 H4NX 117(2) . . ? H4NY N4 H4NX 124(3) . . ? C1B O1YB H4OM 112.2(17) . . ? O1XB C1B O1YB 121.6(2) . . ? O1XB C1B C2B 118.5(2) . . ? O1YB C1B C2B 119.9(2) . . ? C4B O4YB H4OM 108.5(17) . . ? C6 C5 C4 118.7(2) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? O4XB C4B O4YB 119.9(3) . . ? O4XB C4B C3B 118.8(3) . . ? O4YB C4B C3B 121.3(2) . . ? C1' C2' S3' 106.28(15) . . ? C1' C2' H2'1 110.5 . . ? S3' C2' H2'1 110.5 . . ? C1' C2' H2'2 110.5 . . ? S3' C2' H2'2 110.5 . . ? H2'1 C2' H2'2 108.7 . . ? C5B C3B C2B 118.4(2) . . ? C5B C3B C4B 113.2(2) . . ? C2B C3B C4B 128.4(2) . . ? C7B C8B C2B 122.6(2) . . ? C7B C8B H8B 118.7 . . ? C2B C8B H8B 118.7 . . ? C5B C6B C7B 119.0(3) . . ? C5B C6B H6B 120.5 . . ? C7B C6B H6B 120.5 . . ? O5' C5' C4' 109.7(2) . . ? O5' C5' H5'1 109.7 . . ? C4' C5' H5'1 109.7 . . ? O5' C5' H5'2 109.7 . . ? C4' C5' H5'2 109.7 . . ? H5'1 C5' H5'2 108.2 . . ? C6B C7B C8B 119.6(3) . . ? C6B C7B H7B 120.2 . . ? C8B C7B H7B 120.2 . . ? C6B C5B C3B 122.9(2) . . ? C6B C5B H5B 118.5 . . ? C3B C5B H5B 118.5 . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF data_LamSalicylateMonohydrate_107K _database_code_depnum_ccdc_archive 'CCDC 871608' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-(1H)-pyrimidin-2-one salicylate monohydrate ; _chemical_formula_moiety 'C8 H12 N3 O3 S, C7 H5 O3, H2 O' _chemical_formula_sum 'C15 H19 N3 O7 S' _chemical_name_common 'lamivudine salicylate monohydrate' _chemical_compound_source 'Crystal Screening' _chemical_formula_weight 385.40 _chemical_absolute_configuration rmad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.7246(12) _cell_length_b 5.2978(3) _cell_length_c 13.1688(9) _cell_angle_alpha 90 _cell_angle_beta 106.129(8) _cell_angle_gamma 90 _cell_volume 852.80(11) _cell_formula_units_Z 2 _cell_measurement_temperature 107.4(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.293 _exptl_crystal_size_mid 0.076 _exptl_crystal_size_min 0.052 _cell_measurement_reflns_used 1453 _cell_measurement_theta_min 3.4909 _cell_measurement_theta_max 65.9051 _exptl_crystal_density_diffrn 1.501 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.106 _exptl_absorpt_correction_T_min 0.66774 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 107.4(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0651 _diffrn_reflns_av_unetI/netI 0.0636 _diffrn_reflns_number 5257 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -2 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.49 _diffrn_reflns_theta_max 66.01 _diffrn_reflns_theta_full 66.01 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _reflns_number_total 2024 _reflns_number_gt 1700 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.0510P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 2024 _refine_ls_number_parameters 256 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0598 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1063 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(3) _refine_diff_density_max 0.279 _refine_diff_density_min -0.37 _refine_diff_density_rms 0.061 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 O1W O 0.4307(3) 0.2302(8) 0.0893(3) 0.0329(9) Uani 1 1 d . . . S3' S 0.65503(9) 0.2521(2) 0.32849(8) 0.0219(3) Uani 1 1 d . . . N3 N 0.9905(3) -0.1715(7) 0.2390(3) 0.0184(9) Uani 1 1 d . . . O5' O 0.6157(3) 0.4966(7) 0.1053(3) 0.0241(8) Uani 1 1 d . . . O2 O 1.0150(3) -0.0309(7) 0.4074(2) 0.0255(8) Uani 1 1 d . . . N1 N 0.8882(3) 0.1676(7) 0.2741(3) 0.0209(9) Uani 1 1 d . . . N4 N 0.9639(4) -0.3324(8) 0.0721(3) 0.0231(10) Uani 1 1 d . . . O1' O 0.8075(3) 0.5542(6) 0.2978(2) 0.0224(8) Uani 1 1 d . . . C4 C 0.9378(4) -0.1676(8) 0.1343(4) 0.0202(11) Uani 1 1 d . . . C6 C 0.8345(4) 0.1789(8) 0.1692(3) 0.0194(11) Uani 1 1 d . . . H6 H 0.7817 0.3031 0.1456 0.023 Uiso 1 1 calc R . . C5 C 0.8554(4) 0.0157(9) 0.0981(4) 0.0212(11) Uani 1 1 d . . . H5 H 0.8163 0.0241 0.0271 0.025 Uiso 1 1 calc R . . C2 C 0.9691(4) -0.0114(9) 0.3142(4) 0.0209(11) Uani 1 1 d . . . C1' C 0.8636(4) 0.3458(9) 0.3529(4) 0.0215(11) Uani 1 1 d . . . H1' H 0.9323 0.4029 0.402 0.026 Uiso 1 1 calc R . . C2' C 0.7933(4) 0.2190(10) 0.4152(3) 0.0217(11) Uani 1 1 d . . . H2'1 H 0.8008 0.3036 0.4822 0.026 Uiso 1 1 calc R . . H2'2 H 0.8128 0.0426 0.4284 0.026 Uiso 1 1 calc R . . C5' C 0.6253(4) 0.6669(9) 0.1907(3) 0.0219(11) Uani 1 1 d . . . H5'1 H 0.5526 0.7082 0.1956 0.026 Uiso 1 1 calc R . . H5'2 H 0.6588 0.8218 0.1757 0.026 Uiso 1 1 calc R . . C4' C 0.6918(4) 0.5662(9) 0.2959(4) 0.0214(11) Uani 1 1 d . . . H4' H 0.6845 0.6827 0.3514 0.026 Uiso 1 1 calc R . . O2B O 1.2985(3) -0.7613(8) 0.4525(2) 0.0278(8) Uani 1 1 d . . . O1XB O 1.1415(3) -0.5662(6) 0.3063(2) 0.0251(8) Uani 1 1 d . . . O1YB O 1.1130(3) -0.6980(6) 0.1399(2) 0.0273(9) Uani 1 1 d . . . C1B C 1.1619(4) -0.7113(10) 0.2371(3) 0.0209(10) Uani 1 1 d . . . C5B C 1.4087(4) -1.2809(10) 0.3333(4) 0.0282(12) Uani 1 1 d . . . H5B H 1.4628 -1.4035 0.3536 0.034 Uiso 1 1 calc R . . C6B C 1.3442(4) -1.2708(11) 0.2292(4) 0.0249(11) Uani 1 1 d . . . H6B H 1.3543 -1.3874 0.18 0.03 Uiso 1 1 calc R . . C2B C 1.2479(4) -0.9094(9) 0.2719(3) 0.0183(10) Uani 1 1 d . . . C3B C 1.3120(4) -0.9232(10) 0.3778(4) 0.0240(11) Uani 1 1 d . . . C7B C 1.2648(4) -1.0859(10) 0.1993(4) 0.0238(11) Uani 1 1 d . . . H7B H 1.2218 -1.0792 0.1296 0.029 Uiso 1 1 calc R . . C4B C 1.3928(4) -1.1087(9) 0.4071(4) 0.0253(12) Uani 1 1 d . . . H4B H 1.4364 -1.1169 0.4766 0.03 Uiso 1 1 calc R . . H1W H 0.414(5) 0.163(11) 0.032(5) 0.038 Uiso 1 1 d . . . H3 H 1.042(4) -0.284(11) 0.259(4) 0.03 Uiso 1 1 d . . . H2OB H 1.248(5) -0.669(11) 0.423(4) 0.038 Uiso 1 1 d . . . H2W H 0.418(5) 0.131(11) 0.138(4) 0.038 Uiso 1 1 d . . . H5'O H 0.564(5) 0.404(12) 0.099(4) 0.038 Uiso 1 1 d . . . H4NX H 1.015(4) -0.456(11) 0.095(4) 0.03 Uiso 1 1 d . . . H4NY H 0.934(4) -0.316(10) 0.003(4) 0.03 Uiso 1 1 d . . . 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 O1W 0.043(2) 0.032(2) 0.0259(18) -0.007(2) 0.0141(16) -0.008(2) S3' 0.0249(6) 0.0206(6) 0.0212(5) -0.0007(6) 0.0082(4) -0.0021(6) N3 0.017(2) 0.023(2) 0.0176(19) 0.0030(16) 0.0087(16) 0.0052(17) O5' 0.0235(19) 0.027(2) 0.0225(18) -0.0020(15) 0.0080(15) 0.0004(15) O2 0.0264(19) 0.031(2) 0.0189(17) 0.0023(16) 0.0059(14) 0.0054(16) N1 0.024(2) 0.025(2) 0.0157(19) 0.0003(17) 0.0082(16) 0.0008(17) N4 0.031(3) 0.021(2) 0.020(2) 0.0018(18) 0.012(2) 0.0056(18) O1' 0.0209(18) 0.0219(19) 0.0258(17) 0.0012(15) 0.0087(15) 0.0005(15) C4 0.025(3) 0.017(3) 0.022(2) 0.007(2) 0.013(2) -0.001(2) C6 0.021(2) 0.020(3) 0.017(2) 0.003(2) 0.0049(19) -0.002(2) C5 0.024(3) 0.024(3) 0.016(2) 0.001(2) 0.005(2) -0.001(2) C2 0.023(3) 0.019(3) 0.024(3) 0.004(2) 0.012(2) -0.002(2) C1' 0.020(3) 0.023(3) 0.023(2) -0.002(2) 0.007(2) 0.000(2) C2' 0.023(2) 0.025(3) 0.019(2) -0.001(2) 0.0090(18) 0.003(2) C5' 0.023(3) 0.021(3) 0.026(3) 0.000(2) 0.013(2) 0.004(2) C4' 0.021(3) 0.023(3) 0.023(2) -0.003(2) 0.011(2) 0.000(2) O2B 0.036(2) 0.0289(19) 0.0191(16) -0.0012(18) 0.0080(14) 0.011(2) O1XB 0.030(2) 0.0239(19) 0.0231(18) -0.0020(15) 0.0105(15) 0.0041(16) O1YB 0.0299(19) 0.029(2) 0.0195(16) -0.0021(16) 0.0012(14) 0.0080(17) C1B 0.020(2) 0.023(3) 0.022(2) 0.002(2) 0.0092(19) -0.004(2) C5B 0.030(3) 0.023(3) 0.037(3) 0.007(2) 0.017(2) 0.004(2) C6B 0.029(3) 0.022(3) 0.029(2) -0.001(3) 0.016(2) 0.000(3) C2B 0.021(2) 0.016(2) 0.022(2) 0.003(2) 0.013(2) 0.000(2) C3B 0.033(3) 0.024(3) 0.021(2) 0.000(2) 0.016(2) -0.005(2) C7B 0.026(3) 0.026(3) 0.021(2) 0.004(2) 0.010(2) -0.005(2) C4B 0.024(3) 0.028(3) 0.024(3) 0.006(2) 0.007(2) 0.004(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1W H1W 0.81(6) . ? O1W H2W 0.87(6) . ? S3' C4' 1.813(5) . ? S3' C2' 1.820(5) . ? N3 C4 1.355(6) . ? N3 C2 1.387(6) . ? N3 H3 0.88(6) . ? O5' C5' 1.421(5) . ? O5' H5'O 0.81(6) . ? O2 C2 1.207(5) . ? N1 C6 1.361(5) . ? N1 C2 1.391(6) . ? N1 C1' 1.499(6) . ? N4 C4 1.301(6) . ? N4 H4NX 0.91(6) . ? N4 H4NY 0.88(5) . ? O1' C1' 1.402(6) . ? O1' C4' 1.467(5) . ? C4 C5 1.412(7) . ? C6 C5 1.354(6) . ? C6 H6 0.93 . ? C5 H5 0.93 . ? C1' C2' 1.527(6) . ? C1' H1' 0.98 . ? C2' H2'1 0.97 . ? C2' H2'2 0.97 . ? C5' C4' 1.506(6) . ? C5' H5'1 0.97 . ? C5' H5'2 0.97 . ? C4' H4' 0.98 . ? O2B C3B 1.352(6) . ? O2B H2OB 0.82(6) . ? O1XB C1B 1.273(6) . ? O1YB C1B 1.260(5) . ? C1B C2B 1.494(7) . ? C5B C4B 1.387(7) . ? C5B C6B 1.390(6) . ? C5B H5B 0.93 . ? C6B C7B 1.383(7) . ? C6B H6B 0.93 . ? C2B C7B 1.396(7) . ? C2B C3B 1.408(7) . ? C3B C4B 1.397(7) . ? C7B H7B 0.93 . ? C4B H4B 0.93 . ? 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 H1W O1W H2W 111(6) . . ? C4' S3' C2' 88.2(2) . . ? C4 N3 C2 125.3(4) . . ? C4 N3 H3 116(3) . . ? C2 N3 H3 119(3) . . ? C5' O5' H5'O 111(4) . . ? C6 N1 C2 121.7(4) . . ? C6 N1 C1' 122.1(4) . . ? C2 N1 C1' 116.2(4) . . ? C4 N4 H4NX 123(3) . . ? C4 N4 H4NY 118(3) . . ? H4NX N4 H4NY 118(5) . . ? C1' O1' C4' 114.0(3) . . ? N4 C4 N3 119.3(4) . . ? N4 C4 C5 122.9(4) . . ? N3 C4 C5 117.7(4) . . ? C5 C6 N1 122.3(4) . . ? C5 C6 H6 118.9 . . ? N1 C6 H6 118.9 . . ? C6 C5 C4 118.4(4) . . ? C6 C5 H5 120.8 . . ? C4 C5 H5 120.8 . . ? O2 C2 N3 122.5(4) . . ? O2 C2 N1 122.9(4) . . ? N3 C2 N1 114.6(4) . . ? O1' C1' N1 108.2(4) . . ? O1' C1' C2' 109.5(4) . . ? N1 C1' C2' 111.2(4) . . ? O1' C1' H1' 109.3 . . ? N1 C1' H1' 109.3 . . ? C2' C1' H1' 109.3 . . ? C1' C2' S3' 103.2(3) . . ? C1' C2' H2'1 111.1 . . ? S3' C2' H2'1 111.1 . . ? C1' C2' H2'2 111.1 . . ? S3' C2' H2'2 111.1 . . ? H2'1 C2' H2'2 109.1 . . ? O5' C5' C4' 114.0(4) . . ? O5' C5' H5'1 108.8 . . ? C4' C5' H5'1 108.8 . . ? O5' C5' H5'2 108.8 . . ? C4' C5' H5'2 108.8 . . ? H5'1 C5' H5'2 107.7 . . ? O1' C4' C5' 109.7(4) . . ? O1' C4' S3' 106.3(3) . . ? C5' C4' S3' 115.3(3) . . ? O1' C4' H4' 108.5 . . ? C5' C4' H4' 108.5 . . ? S3' C4' H4' 108.5 . . ? C3B O2B H2OB 106(4) . . ? O1YB C1B O1XB 123.6(5) . . ? O1YB C1B C2B 117.6(4) . . ? O1XB C1B C2B 118.8(4) . . ? C4B C5B C6B 120.3(5) . . ? C4B C5B H5B 119.9 . . ? C6B C5B H5B 119.9 . . ? C7B C6B C5B 119.5(5) . . ? C7B C6B H6B 120.3 . . ? C5B C6B H6B 120.3 . . ? C7B C2B C3B 119.1(4) . . ? C7B C2B C1B 120.0(4) . . ? C3B C2B C1B 120.9(4) . . ? O2B C3B C4B 118.6(4) . . ? O2B C3B C2B 122.1(4) . . ? C4B C3B C2B 119.3(4) . . ? C6B C7B C2B 121.2(5) . . ? C6B C7B H7B 119.4 . . ? C2B C7B H7B 119.4 . . ? C5B C4B C3B 120.6(4) . . ? C5B C4B H4B 119.7 . . ? C3B C4B H4B 119.7 . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF