# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Gautam Desiraju' _publ_contact_author_address ; School of Chemistry University of Hyderabad PO Central University Hyderabad A. P. 500046 INDIA ; _publ_contact_author_email 'GAUTAM DESIRAJU@YAHOO.COM' _publ_section_title ; Tautomeric polymorphism in omeprazole ; _publ_contact_author ; Prof. Gautam R. Desiraju School of Chemistry Univerisity of Hyderabad Hyderabad 500 046 India ; _publ_contact_author_fax '91 40 23010567' _publ_contact_author_phone '91 40 23134828' loop_ _publ_author_name 'Gautam Desiraju' 'Prashant Bhatt' data_grd463_I _database_code_depnum_ccdc_archive 'CCDC 633382' _chemical_name_systematic ; 6-methoxy-2-{(4-methoxy-3,5-dimethyl-2-pyridinyl)methylsulfinyl} -1H-benzimidazole ; _chemical_name_common ; 6-methoxy-2-((4-methoxy-3,5-dimethyl-2- pyridinyl)methylsulfinyl) -1H-benzimidazole ; _chemical_melting_point 156 _chemical_formula_moiety 'C17 H19 N3 O3 S' _chemical_formula_sum 'C17 H19 N3 O3 S' _chemical_formula_weight 345 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_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6421(9) _cell_length_b 10.3865(10) _cell_length_c 10.1539(10) _cell_angle_alpha 89.929(2) _cell_angle_beta 110.939(2) _cell_angle_gamma 116.937(2) _cell_volume 830.78(14) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2992 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 26.01 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 0.216 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9197 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _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 2.19 _diffrn_reflns_theta_max 26.03 _reflns_number_total 3262 _reflns_number_gt 2723 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0477P)^2^+0.8800P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3262 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0690 _refine_ls_R_factor_gt 0.0566 _refine_ls_wR_factor_ref 0.1268 _refine_ls_wR_factor_gt 0.1209 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _refine_ls_shift/su_max 0.000 _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 N1 N 0.7323(3) 0.2409(2) 0.5668(2) 0.0177(5) Uani 1 1 d . . . H1 H 0.696(4) 0.156(3) 0.520(3) 0.026(8) Uiso 1 1 d . . . C2 C 0.6271(3) 0.2817(3) 0.5927(3) 0.0172(5) Uani 1 1 d . . . N3 N 0.7018(3) 0.4171(2) 0.6622(2) 0.0190(5) Uani 1 1 d . . . C3A C 0.8695(3) 0.4719(3) 0.6814(3) 0.0184(5) Uani 1 1 d . . . C4 C 1.0078(3) 0.6137(3) 0.7423(3) 0.0214(6) Uani 1 1 d . . . H4 H 0.9962 0.6878 0.7804 0.026 Uiso 1 1 calc R . . C5 C 1.1607(3) 0.6392(3) 0.7435(3) 0.0219(6) Uani 1 1 d . . . H5 H 1.2542 0.7325 0.7832 0.026 Uiso 1 1 calc R . . C6 C 1.1802(3) 0.5274(3) 0.6860(3) 0.0204(6) Uani 1 1 d . . . C7 C 1.0455(3) 0.3864(3) 0.6252(3) 0.0179(5) Uani 1 1 d . . . H7 H 1.0576 0.3122 0.5880 0.021 Uiso 1 1 calc R . . C7A C 0.8907(3) 0.3629(3) 0.6235(3) 0.0175(5) Uani 1 1 d . . . C8 C 0.3477(3) 0.1222(3) 0.3533(3) 0.0215(6) Uani 1 1 d . . . H8A H 0.3828 0.2122 0.3156 0.026 Uiso 1 1 calc R . . H8B H 0.4045 0.0714 0.3358 0.026 Uiso 1 1 calc R . . C9 C 0.1573(3) 0.0255(3) 0.2783(3) 0.0191(5) Uani 1 1 d . . . C10 C 0.0841(3) -0.0851(3) 0.1588(3) 0.0202(6) Uani 1 1 d . . . C11 C -0.0926(3) -0.1572(3) 0.0907(3) 0.0218(6) Uani 1 1 d . . . C12 C -0.1897(3) -0.1223(3) 0.1421(3) 0.0244(6) Uani 1 1 d . . . C13 C -0.1012(3) -0.0140(3) 0.2655(3) 0.0261(6) Uani 1 1 d . . . H13 H -0.1637 0.0085 0.3038 0.031 Uiso 1 1 calc R . . C14 C 0.1855(3) -0.1263(3) 0.1013(3) 0.0253(6) Uani 1 1 d . . . H14A H 0.3032 -0.0536 0.1464 0.038 Uiso 1 1 calc R . . H14B H 0.1458 -0.1310 -0.0007 0.038 Uiso 1 1 calc R . . H14C H 0.1720 -0.2205 0.1217 0.038 Uiso 1 1 calc R . . C15 C -0.3807(4) -0.1939(3) 0.0669(3) 0.0342(7) Uani 1 1 d . . . H15A H -0.4309 -0.2906 0.0881 0.051 Uiso 1 1 calc R . . H15B H -0.4127 -0.2013 -0.0350 0.051 Uiso 1 1 calc R . . H15C H -0.4198 -0.1354 0.0998 0.051 Uiso 1 1 calc R . . C16 C -0.2247(4) -0.4080(3) -0.0114(3) 0.0352(7) Uani 1 1 d . . . H16A H -0.3085 -0.4355 0.0284 0.053 Uiso 1 1 calc R . . H16B H -0.1287 -0.4146 0.0541 0.053 Uiso 1 1 calc R . . H16C H -0.2726 -0.4732 -0.1013 0.053 Uiso 1 1 calc R . . C17 C 1.3695(4) 0.4590(3) 0.6494(3) 0.0273(6) Uani 1 1 d . . . H17A H 1.2988 0.4193 0.5492 0.041 Uiso 1 1 calc R . . H17B H 1.3426 0.3820 0.7035 0.041 Uiso 1 1 calc R . . H17C H 1.4866 0.5008 0.6639 0.041 Uiso 1 1 calc R . . O1 O 1.3406(2) 0.5707(2) 0.6966(2) 0.0258(4) Uani 1 1 d . . . O2 O 0.3853(2) 0.02482(19) 0.59810(19) 0.0213(4) Uani 1 1 d . . . O3 O -0.1714(2) -0.2597(2) -0.03442(19) 0.0277(5) Uani 1 1 d . . . N4 N 0.0678(3) 0.0599(2) 0.3326(2) 0.0236(5) Uani 1 1 d . . . S1 S 0.40640(8) 0.16562(7) 0.54452(7) 0.01781(18) Uani 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 N1 0.0149(11) 0.0141(11) 0.0198(11) -0.0013(9) 0.0054(9) 0.0046(9) C2 0.0124(12) 0.0177(13) 0.0163(13) 0.0011(10) 0.0046(10) 0.0040(10) N3 0.0135(11) 0.0186(11) 0.0182(11) -0.0026(9) 0.0033(9) 0.0047(9) C3A 0.0177(13) 0.0218(13) 0.0127(12) 0.0014(10) 0.0037(11) 0.0088(11) C4 0.0199(14) 0.0184(13) 0.0207(14) -0.0014(11) 0.0051(11) 0.0076(11) C5 0.0171(13) 0.0167(13) 0.0214(14) 0.0006(11) 0.0025(11) 0.0039(11) C6 0.0153(13) 0.0254(14) 0.0189(13) 0.0093(11) 0.0053(11) 0.0099(11) C7 0.0187(13) 0.0214(13) 0.0141(12) 0.0041(10) 0.0054(11) 0.0111(11) C7A 0.0180(13) 0.0189(13) 0.0132(12) 0.0046(10) 0.0052(10) 0.0079(11) C8 0.0198(14) 0.0236(14) 0.0151(13) -0.0009(11) 0.0063(11) 0.0061(11) C9 0.0187(13) 0.0180(13) 0.0179(13) 0.0054(10) 0.0064(11) 0.0075(11) C10 0.0223(14) 0.0189(13) 0.0146(13) 0.0053(10) 0.0060(11) 0.0073(11) C11 0.0238(14) 0.0178(13) 0.0143(13) 0.0058(11) 0.0045(11) 0.0050(11) C12 0.0183(14) 0.0236(14) 0.0236(15) 0.0085(12) 0.0052(12) 0.0066(12) C13 0.0206(14) 0.0272(15) 0.0292(15) 0.0062(12) 0.0102(12) 0.0104(12) C14 0.0230(15) 0.0260(15) 0.0194(14) 0.0000(12) 0.0062(12) 0.0077(12) C15 0.0203(15) 0.0374(17) 0.0321(17) 0.0089(14) 0.0049(13) 0.0082(13) C16 0.0388(18) 0.0245(16) 0.0225(15) -0.0033(12) 0.0077(14) 0.0032(13) C17 0.0247(15) 0.0306(16) 0.0355(17) 0.0095(13) 0.0151(13) 0.0181(13) O1 0.0167(10) 0.0242(10) 0.0353(11) 0.0035(9) 0.0091(9) 0.0099(8) O2 0.0198(10) 0.0192(9) 0.0223(10) 0.0009(8) 0.0093(8) 0.0068(8) O3 0.0259(11) 0.0248(10) 0.0154(9) 0.0009(8) 0.0025(8) 0.0033(9) N4 0.0183(12) 0.0234(12) 0.0253(12) 0.0032(10) 0.0081(10) 0.0076(10) S1 0.0137(3) 0.0168(3) 0.0190(3) -0.0024(2) 0.0060(3) 0.0047(2) _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 N1 C2 1.363(3) . ? N1 C7A 1.375(3) . ? N1 H1 0.85(3) . ? C2 N3 1.310(3) . ? C2 S1 1.776(2) . ? N3 C3A 1.385(3) . ? C3A C4 1.401(4) . ? C3A C7A 1.402(3) . ? C4 C5 1.370(4) . ? C4 H4 0.9300 . ? C5 C6 1.415(4) . ? C5 H5 0.9300 . ? C6 O1 1.363(3) . ? C6 C7 1.385(4) . ? C7 C7A 1.392(3) . ? C7 H7 0.9300 . ? C8 C9 1.513(4) . ? C8 S1 1.811(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N4 1.341(3) . ? C9 C10 1.395(4) . ? C10 C11 1.395(4) . ? C10 C14 1.504(4) . ? C11 O3 1.381(3) . ? C11 C12 1.391(4) . ? C12 C13 1.390(4) . ? C12 C15 1.511(4) . ? C13 N4 1.335(3) . ? C13 H13 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 O3 1.435(3) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 O1 1.429(3) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? O2 S1 1.5111(18) . ? 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 N1 C7A 105.7(2) . . ? C2 N1 H1 122(2) . . ? C7A N1 H1 132(2) . . ? N3 C2 N1 114.8(2) . . ? N3 C2 S1 119.99(18) . . ? N1 C2 S1 125.19(19) . . ? C2 N3 C3A 103.7(2) . . ? N3 C3A C4 129.8(2) . . ? N3 C3A C7A 110.3(2) . . ? C4 C3A C7A 119.8(2) . . ? C5 C4 C3A 117.6(2) . . ? C5 C4 H4 121.2 . . ? C3A C4 H4 121.2 . . ? C4 C5 C6 121.8(2) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? O1 C6 C7 123.9(2) . . ? O1 C6 C5 114.4(2) . . ? C7 C6 C5 121.7(2) . . ? C6 C7 C7A 115.7(2) . . ? C6 C7 H7 122.2 . . ? C7A C7 H7 122.2 . . ? N1 C7A C7 131.0(2) . . ? N1 C7A C3A 105.6(2) . . ? C7 C7A C3A 123.4(2) . . ? C9 C8 S1 109.48(17) . . ? C9 C8 H8A 109.8 . . ? S1 C8 H8A 109.8 . . ? C9 C8 H8B 109.8 . . ? S1 C8 H8B 109.8 . . ? H8A C8 H8B 108.2 . . ? N4 C9 C10 123.9(2) . . ? N4 C9 C8 114.3(2) . . ? C10 C9 C8 121.8(2) . . ? C9 C10 C11 116.3(2) . . ? C9 C10 C14 123.5(2) . . ? C11 C10 C14 120.2(2) . . ? O3 C11 C12 119.6(2) . . ? O3 C11 C10 118.8(2) . . ? C12 C11 C10 121.4(2) . . ? C13 C12 C11 116.4(2) . . ? C13 C12 C15 121.1(3) . . ? C11 C12 C15 122.5(3) . . ? N4 C13 C12 124.3(3) . . ? N4 C13 H13 117.8 . . ? C12 C13 H13 117.8 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? 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 . . ? O3 C16 H16A 109.5 . . ? O3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O1 C17 H17A 109.5 . . ? O1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C6 O1 C17 116.4(2) . . ? C11 O3 C16 113.4(2) . . ? C13 N4 C9 117.6(2) . . ? O2 S1 C2 107.06(11) . . ? O2 S1 C8 105.38(11) . . ? C2 S1 C8 96.83(12) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.578 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.065 #===END data_grd498_II _database_code_depnum_ccdc_archive 'CCDC 633383' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5(6)-methoxy-2-{(4-methoxy-3,5-dimethyl-2-pyridinyl)methylsulfinyl} -1H-benzimidazole ; _chemical_name_common ; 5(6)-methoxy-2-((4-methoxy-3,5-dimethyl-2- pyridinyl)methylsulfinyl) -1H-benzimidazole ; _chemical_melting_point ? _chemical_formula_moiety 'C17 H19 N3 O3 S' _chemical_formula_sum 'C17 H19 N3 O3 S' _chemical_formula_weight 345 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_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.667(7) _cell_length_b 10.337(8) _cell_length_c 10.292(8) _cell_angle_alpha 90.044(12) _cell_angle_beta 111.552(12) _cell_angle_gamma 116.451(11) _cell_volume 839.6(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1460 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 25.88 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.366 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7586 _diffrn_reflns_av_R_equivalents 0.0563 _diffrn_reflns_av_sigmaI/netI 0.0898 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _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 2.17 _diffrn_reflns_theta_max 26.07 _reflns_number_total 3248 _reflns_number_gt 1950 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. Because of low occupancy of 0.076(4) oxygen O1B could not be refined anisotropically. Both O1B and C17B were refined isotropically with fixed Uiso values of 0.035. ; _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^)+(0.0701P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3248 _refine_ls_number_parameters 237 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.1093 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1411 _refine_ls_wR_factor_gt 0.1196 _refine_ls_goodness_of_fit_ref 0.981 _refine_ls_restrained_S_all 0.978 _refine_ls_shift/su_max 0.000 _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 N1 N 0.7327(3) 0.2421(3) 0.5663(3) 0.0272(7) Uani 1 1 d . . . C2 C 0.6279(3) 0.2830(3) 0.5909(3) 0.0280(7) Uani 1 1 d . . . N3 N 0.7033(3) 0.4202(3) 0.6602(3) 0.0310(7) Uani 1 1 d . . . C3A C 0.8705(4) 0.4738(3) 0.6796(3) 0.0305(8) Uani 1 1 d . . . C4 C 1.0089(4) 0.6160(4) 0.7407(3) 0.0332(8) Uani 1 1 d . A . H4 H 0.9972 0.6905 0.7783 0.040 Uiso 1 1 calc R . . C5 C 1.1614(4) 0.6416(4) 0.7430(3) 0.0348(8) Uani 1 1 d U . . C6 C 1.1800(4) 0.5281(4) 0.6867(3) 0.0330(8) Uani 1 1 d U A . C7 C 1.0462(4) 0.3859(3) 0.6248(3) 0.0306(8) Uani 1 1 d . . . H7 H 1.0585 0.3115 0.5878 0.037 Uiso 1 1 calc R A . C7A C 0.8919(4) 0.3640(3) 0.6228(3) 0.0280(7) Uani 1 1 d . A . C8 C 0.3467(3) 0.1233(3) 0.3535(3) 0.0300(8) Uani 1 1 d . . . H8A H 0.3800 0.2129 0.3155 0.036 Uiso 1 1 calc R . . H8B H 0.4038 0.0723 0.3366 0.036 Uiso 1 1 calc R . . C9 C 0.1559(4) 0.0255(3) 0.2792(3) 0.0274(7) Uani 1 1 d . . . C10 C 0.0835(4) -0.0835(3) 0.1590(3) 0.0289(8) Uani 1 1 d . . . C11 C -0.0934(4) -0.1578(3) 0.0927(3) 0.0313(8) Uani 1 1 d . . . C12 C -0.1904(4) -0.1262(4) 0.1452(3) 0.0344(8) Uani 1 1 d . . . C13 C -0.1020(4) -0.0188(4) 0.2697(4) 0.0375(9) Uani 1 1 d . . . H13 H -0.1645 0.0016 0.3089 0.045 Uiso 1 1 calc R . . C14 C 0.1866(4) -0.1202(4) 0.1004(3) 0.0388(9) Uani 1 1 d . . . H14A H 0.2096 -0.1939 0.1458 0.058 Uiso 1 1 calc R . . H14B H 0.2915 -0.0331 0.1187 0.058 Uiso 1 1 calc R . . H14C H 0.1241 -0.1572 -0.0004 0.058 Uiso 1 1 calc R . . C15 C -0.3827(4) -0.1996(4) 0.0722(4) 0.0501(10) Uani 1 1 d . . . H15A H -0.4299 -0.2999 0.0848 0.075 Uiso 1 1 calc R . . H15B H -0.4172 -0.1980 -0.0277 0.075 Uiso 1 1 calc R . . H15C H -0.4224 -0.1474 0.1132 0.075 Uiso 1 1 calc R . . C16 C -0.2187(5) -0.4078(4) -0.0120(4) 0.0499(11) Uani 1 1 d . . . H16A H -0.2995 -0.4379 0.0297 0.075 Uiso 1 1 calc R . . H16B H -0.1197 -0.4125 0.0505 0.075 Uiso 1 1 calc R . . H16C H -0.2680 -0.4724 -0.1020 0.075 Uiso 1 1 calc R . . C17A C 1.3687(4) 0.4592(4) 0.6506(4) 0.0371(10) Uani 0.922(3) 1 d PU A 1 H17A H 1.2986 0.4208 0.5507 0.056 Uiso 0.922(3) 1 calc PR A 1 H17B H 1.3407 0.3812 0.7026 0.056 Uiso 0.922(3) 1 calc PR A 1 H17C H 1.4857 0.5000 0.6666 0.056 Uiso 0.922(3) 1 calc PR A 1 O1A O 1.3408(2) 0.5714(2) 0.6981(2) 0.0328(7) Uani 0.922(3) 1 d PU A 1 C17B C 1.339(5) 0.839(5) 0.839(4) 0.035 Uiso 0.078(3) 1 d PU A 2 H17D H 1.3063 0.8060 0.9151 0.052 Uiso 0.078(3) 1 calc PR A 2 H17E H 1.2576 0.8624 0.7723 0.052 Uiso 0.078(3) 1 calc PR A 2 H17F H 1.4486 0.9248 0.8763 0.052 Uiso 0.078(3) 1 calc PR A 2 O1B O 1.345(4) 0.731(3) 0.771(3) 0.035 Uiso 0.078(3) 1 d PU A 2 O2 O 0.3868(2) 0.0278(2) 0.5965(2) 0.0304(5) Uani 1 1 d . . . O3 O -0.1723(3) -0.2596(2) -0.0333(2) 0.0372(6) Uani 1 1 d . . . N4 N 0.0673(3) 0.0567(3) 0.3359(3) 0.0336(7) Uani 1 1 d . . . S1 S 0.40772(9) 0.16883(9) 0.54314(8) 0.0294(2) Uani 1 1 d . . . H1 H 0.706(4) 0.166(3) 0.523(3) 0.025(9) Uiso 1 1 d . . . H5 H 1.263(5) 0.738(5) 0.781(4) 0.039(10) Uiso 0.92 1 d P . . 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 N1 0.0188(13) 0.0219(16) 0.0293(15) -0.0040(12) 0.0058(11) 0.0036(12) C2 0.0178(15) 0.0275(18) 0.0261(17) -0.0048(13) 0.0046(12) 0.0043(14) N3 0.0209(13) 0.0325(16) 0.0259(15) -0.0058(12) 0.0053(11) 0.0052(12) C3A 0.0232(16) 0.0303(19) 0.0240(17) -0.0021(14) 0.0032(13) 0.0068(14) C4 0.0240(16) 0.0308(19) 0.0283(18) -0.0050(14) 0.0016(13) 0.0072(14) C5 0.0247(17) 0.0286(19) 0.0333(19) 0.0013(15) 0.0030(14) 0.0056(16) C6 0.0162(15) 0.040(2) 0.0295(18) 0.0106(15) 0.0028(13) 0.0085(14) C7 0.0261(17) 0.0313(19) 0.0293(18) 0.0082(14) 0.0077(14) 0.0125(15) C7A 0.0199(15) 0.0294(18) 0.0240(16) 0.0021(13) 0.0046(12) 0.0066(14) C8 0.0205(15) 0.0285(18) 0.0262(17) -0.0021(13) 0.0068(13) 0.0022(14) C9 0.0230(15) 0.0259(17) 0.0272(17) 0.0046(13) 0.0077(13) 0.0090(14) C10 0.0207(15) 0.0282(18) 0.0257(17) 0.0044(14) 0.0064(13) 0.0045(14) C11 0.0259(16) 0.0274(18) 0.0217(17) 0.0044(13) 0.0030(13) 0.0028(14) C12 0.0208(16) 0.038(2) 0.0304(18) 0.0060(15) 0.0048(14) 0.0072(15) C13 0.0239(17) 0.039(2) 0.045(2) 0.0045(16) 0.0141(15) 0.0113(16) C14 0.0284(17) 0.048(2) 0.0262(18) -0.0044(15) 0.0067(14) 0.0112(16) C15 0.0218(17) 0.058(3) 0.050(2) 0.0050(19) 0.0058(16) 0.0106(18) C16 0.052(2) 0.035(2) 0.030(2) -0.0088(16) 0.0073(17) 0.0019(18) C17A 0.0282(19) 0.038(2) 0.047(2) 0.0072(18) 0.0124(17) 0.0197(17) O1A 0.0154(11) 0.0308(14) 0.0449(15) 0.0005(11) 0.0061(10) 0.0100(10) O2 0.0225(11) 0.0271(12) 0.0317(12) -0.0015(9) 0.0092(9) 0.0055(10) O3 0.0306(12) 0.0333(13) 0.0234(12) 0.0002(10) 0.0038(9) 0.0015(10) N4 0.0220(13) 0.0336(16) 0.0365(16) -0.0009(12) 0.0089(12) 0.0088(12) S1 0.0185(4) 0.0278(5) 0.0292(5) -0.0063(3) 0.0059(3) 0.0039(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 N1 C2 1.356(4) . ? N1 C7A 1.381(4) . ? N1 H1 0.79(3) . ? C2 N3 1.322(4) . ? C2 S1 1.777(3) . ? N3 C3A 1.387(4) . ? C3A C7A 1.404(4) . ? C3A C4 1.405(4) . ? C4 C5 1.368(5) . ? C4 H4 0.9300 . ? C5 C6 1.416(5) . ? C5 O1B 1.50(3) . ? C5 H5 0.98(4) . ? C6 O1A 1.370(4) . ? C6 C7 1.393(4) . ? C7 C7A 1.398(4) . ? C7 H7 0.9300 . ? C8 C9 1.520(4) . ? C8 S1 1.813(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N4 1.338(4) . ? C9 C10 1.395(4) . ? C10 C11 1.398(4) . ? C10 C14 1.510(4) . ? C11 C12 1.387(5) . ? C11 O3 1.388(3) . ? C12 C13 1.397(4) . ? C12 C15 1.521(4) . ? C13 N4 1.340(4) . ? C13 H13 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 O3 1.435(4) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17A O1A 1.426(4) . ? C17A H17A 0.9600 . ? C17A H17B 0.9600 . ? C17A H17C 0.9600 . ? C17B O1B 1.35(5) . ? C17B H17D 0.9600 . ? C17B H17E 0.9600 . ? C17B H17F 0.9600 . ? C17B H5 0.99(4) . ? O1B H5 0.87(4) . ? O2 S1 1.512(2) . ? 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 N1 C7A 106.4(3) . . ? C2 N1 H1 127(2) . . ? C7A N1 H1 127(2) . . ? N3 C2 N1 114.4(3) . . ? N3 C2 S1 119.5(2) . . ? N1 C2 S1 126.0(2) . . ? C2 N3 C3A 103.5(3) . . ? N3 C3A C7A 110.7(3) . . ? N3 C3A C4 129.6(3) . . ? C7A C3A C4 119.7(3) . . ? C5 C4 C3A 117.9(3) . . ? C5 C4 H4 121.0 . . ? C3A C4 H4 121.0 . . ? C4 C5 C6 121.2(3) . . ? C4 C5 O1B 156.5(13) . . ? C6 C5 O1B 82.3(12) . . ? C4 C5 H5 123(2) . . ? C6 C5 H5 116(2) . . ? O1B C5 H5 33(2) . . ? O1A C6 C7 123.3(3) . . ? O1A C6 C5 113.9(3) . . ? C7 C6 C5 122.8(3) . . ? C6 C7 C7A 114.6(3) . . ? C6 C7 H7 122.7 . . ? C7A C7 H7 122.7 . . ? N1 C7A C7 131.1(3) . . ? N1 C7A C3A 105.0(3) . . ? C7 C7A C3A 123.8(3) . . ? C9 C8 S1 109.4(2) . . ? C9 C8 H8A 109.8 . . ? S1 C8 H8A 109.8 . . ? C9 C8 H8B 109.8 . . ? S1 C8 H8B 109.8 . . ? H8A C8 H8B 108.2 . . ? N4 C9 C10 124.3(3) . . ? N4 C9 C8 114.4(3) . . ? C10 C9 C8 121.2(3) . . ? C9 C10 C11 116.0(3) . . ? C9 C10 C14 123.2(3) . . ? C11 C10 C14 120.7(3) . . ? C12 C11 O3 119.7(3) . . ? C12 C11 C10 121.6(3) . . ? O3 C11 C10 118.6(3) . . ? C11 C12 C13 116.5(3) . . ? C11 C12 C15 123.1(3) . . ? C13 C12 C15 120.4(3) . . ? N4 C13 C12 124.0(3) . . ? N4 C13 H13 118.0 . . ? C12 C13 H13 118.0 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? 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 . . ? O3 C16 H16A 109.5 . . ? O3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C6 O1A C17A 116.1(3) . . ? O1B C17B H17D 109.5 . . ? O1B C17B H17E 109.5 . . ? H17D C17B H17E 109.5 . . ? O1B C17B H17F 109.5 . . ? H17D C17B H17F 109.5 . . ? H17E C17B H17F 109.5 . . ? O1B C17B H5 40(3) . . ? H17D C17B H5 90.1 . . ? H17E C17B H5 84.7 . . ? H17F C17B H5 149.1 . . ? C17B O1B C5 85(3) . . ? C17B O1B H5 47(3) . . ? C5 O1B H5 38(3) . . ? C11 O3 C16 113.3(2) . . ? C9 N4 C13 117.5(3) . . ? O2 S1 C2 106.98(14) . . ? O2 S1 C8 105.22(14) . . ? C2 S1 C8 96.75(14) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 26.07 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.348 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.063 #===END data_grd503_III _database_code_depnum_ccdc_archive 'CCDC 633384' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5(6)-methoxy-2-{(4-methoxy-3,5-dimethyl-2-pyridinyl)methylsulfinyl} -1H-benzimidazole ; _chemical_name_common ; 5(6)-methoxy-2-((4-methoxy-3,5-dimethyl-2- pyridinyl)methylsulfinyl) -1H-benzimidazole ; _chemical_melting_point 156 _chemical_formula_moiety 'C17 H19 N3 O3 S' _chemical_formula_sum 'C17 H19 N3 O3 S' _chemical_formula_weight 345 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_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.638(5) _cell_length_b 10.264(5) _cell_length_c 10.324(5) _cell_angle_alpha 90.085(9) _cell_angle_beta 111.732(8) _cell_angle_gamma 116.288(8) _cell_volume 833.7(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1082 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 23.46 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6800 _diffrn_reflns_av_R_equivalents 0.0563 _diffrn_reflns_av_sigmaI/netI 0.1025 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _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 2.17 _diffrn_reflns_theta_max 26.10 _reflns_number_total 3281 _reflns_number_gt 1824 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0912P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3281 _refine_ls_number_parameters 249 _refine_ls_number_restraints 39 _refine_ls_R_factor_all 0.1318 _refine_ls_R_factor_gt 0.0620 _refine_ls_wR_factor_ref 0.1795 _refine_ls_wR_factor_gt 0.1449 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.983 _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 N1 N 0.7325(4) 0.2416(4) 0.5657(3) 0.0319(8) Uani 1 1 d . . . H1 H 0.696(5) 0.159(4) 0.511(4) 0.035(12) Uiso 1 1 d . . . C2 C 0.6281(5) 0.2848(4) 0.5904(4) 0.0327(9) Uani 1 1 d . . . N3 N 0.7042(4) 0.4223(4) 0.6599(3) 0.0369(9) Uani 1 1 d . . . C3A C 0.8712(5) 0.4753(4) 0.6795(4) 0.0349(10) Uani 1 1 d . . . C4 C 1.0095(5) 0.6175(5) 0.7409(4) 0.0410(11) Uani 1 1 d . A . H4 H 0.9976 0.6938 0.7799 0.049 Uiso 1 1 calc R . . C5 C 1.1636(5) 0.6434(5) 0.7433(4) 0.0394(10) Uani 1 1 d U . . H5 H 1.274(6) 0.750(5) 0.787(5) 0.025(12) Uiso 0.90 1 d P . . C6 C 1.1805(4) 0.5293(5) 0.6867(4) 0.0375(10) Uani 1 1 d U A . C7 C 1.0465(4) 0.3856(5) 0.6249(4) 0.0357(10) Uani 1 1 d . . . H7 H 1.0591 0.3089 0.5874 0.043 Uiso 1 1 calc R A . C7A C 0.8921(4) 0.3646(4) 0.6231(4) 0.0326(9) Uani 1 1 d . A . C8 C 0.3470(4) 0.1245(4) 0.3545(4) 0.0357(10) Uani 1 1 d . . . H8A H 0.3799 0.2165 0.3159 0.043 Uiso 1 1 calc R . . H8B H 0.4063 0.0730 0.3374 0.043 Uiso 1 1 calc R . . C9 C 0.1566(4) 0.0254(4) 0.2800(4) 0.0295(9) Uani 1 1 d . . . C10 C 0.0832(5) -0.0822(4) 0.1595(4) 0.0317(9) Uani 1 1 d . . . C11 C -0.0930(5) -0.1574(4) 0.0940(4) 0.0354(10) Uani 1 1 d . . . C12 C -0.1898(5) -0.1272(5) 0.1480(4) 0.0379(10) Uani 1 1 d . . . C13 C -0.1020(5) -0.0218(5) 0.2719(4) 0.0422(11) Uani 1 1 d . . . H13 H -0.1663 -0.0032 0.3131 0.051 Uiso 1 1 calc R . . C14 C 0.1866(5) -0.1175(5) 0.0991(4) 0.0433(11) Uani 1 1 d . . . H14A H 0.2862 -0.0254 0.1068 0.065 Uiso 1 1 calc R . . H14B H 0.1166 -0.1665 -0.0012 0.065 Uiso 1 1 calc R . . H14C H 0.2239 -0.1833 0.1525 0.065 Uiso 1 1 calc R . . C15 C -0.3820(5) -0.2024(6) 0.0754(5) 0.0573(14) Uani 1 1 d . . . H15A H -0.4287 -0.3053 0.0886 0.086 Uiso 1 1 calc R . . H15B H -0.4181 -0.2010 -0.0264 0.086 Uiso 1 1 calc R . . H15C H -0.4236 -0.1496 0.1172 0.086 Uiso 1 1 calc R . . C16 C -0.2160(6) -0.4065(5) -0.0117(5) 0.0549(13) Uani 1 1 d . . . H16A H -0.1139 -0.4098 0.0531 0.082 Uiso 1 1 calc R . . H16B H -0.2643 -0.4722 -0.1033 0.082 Uiso 1 1 calc R . . H16C H -0.2999 -0.4392 0.0294 0.082 Uiso 1 1 calc R . . C17A C 1.3681(6) 0.4589(5) 0.6503(5) 0.0412(12) Uani 0.901(4) 1 d PU A 1 H17A H 1.3403 0.3791 0.7035 0.062 Uiso 0.901(4) 1 calc PR A 1 H17B H 1.4875 0.5004 0.6658 0.062 Uiso 0.901(4) 1 calc PR A 1 H17C H 1.2952 0.4192 0.5487 0.062 Uiso 0.901(4) 1 calc PR A 1 O1A O 1.3409(3) 0.5724(3) 0.6983(3) 0.0375(8) Uani 0.901(4) 1 d PU A 1 C17B C 1.345(5) 0.848(4) 0.844(4) 0.025(8) Uani 0.099(4) 1 d PU A 2 H17D H 1.2529 0.8662 0.7826 0.038 Uiso 0.099(4) 1 calc PR A 2 H17E H 1.4547 0.9372 0.8673 0.038 Uiso 0.099(4) 1 calc PR A 2 H17F H 1.3317 0.8233 0.9313 0.038 Uiso 0.099(4) 1 calc PR A 2 O1B O 1.342(3) 0.730(3) 0.772(2) 0.025(5) Uani 0.099(4) 1 d PU A 2 O2 O 0.3884(3) 0.0295(3) 0.5968(3) 0.0331(7) Uani 1 1 d . . . O3 O -0.1729(3) -0.2595(3) -0.0325(3) 0.0403(7) Uani 1 1 d . . . N4 N 0.0670(4) 0.0556(4) 0.3377(3) 0.0366(8) Uani 1 1 d . . . S1 S 0.40879(12) 0.17029(11) 0.54290(10) 0.0326(3) Uani 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 N1 0.0247(18) 0.030(2) 0.0330(19) -0.0033(16) 0.0107(15) 0.0074(16) C2 0.025(2) 0.033(2) 0.028(2) -0.0066(18) 0.0074(17) 0.0067(18) N3 0.0283(18) 0.039(2) 0.0337(19) -0.0032(16) 0.0125(15) 0.0089(16) C3A 0.030(2) 0.031(2) 0.035(2) -0.0012(19) 0.0109(18) 0.0098(18) C4 0.030(2) 0.039(3) 0.035(2) -0.0054(19) 0.0079(18) 0.0056(19) C5 0.029(2) 0.032(2) 0.040(2) -0.001(2) 0.0072(19) 0.0065(19) C6 0.0179(19) 0.044(3) 0.039(2) 0.012(2) 0.0086(17) 0.0076(18) C7 0.028(2) 0.038(3) 0.036(2) 0.0098(19) 0.0103(18) 0.0143(19) C7A 0.023(2) 0.032(2) 0.030(2) 0.0060(18) 0.0088(16) 0.0047(17) C8 0.024(2) 0.031(2) 0.042(2) -0.0001(19) 0.0166(18) 0.0024(17) C9 0.028(2) 0.026(2) 0.029(2) 0.0042(17) 0.0123(17) 0.0078(17) C10 0.028(2) 0.032(2) 0.032(2) 0.0091(18) 0.0164(17) 0.0096(18) C11 0.030(2) 0.033(2) 0.028(2) 0.0045(18) 0.0100(17) 0.0048(18) C12 0.023(2) 0.040(3) 0.038(2) 0.006(2) 0.0108(18) 0.0051(18) C13 0.030(2) 0.045(3) 0.049(3) 0.006(2) 0.021(2) 0.013(2) C14 0.037(2) 0.052(3) 0.035(2) -0.003(2) 0.0199(19) 0.014(2) C15 0.028(2) 0.073(4) 0.056(3) 0.005(3) 0.015(2) 0.014(2) C16 0.062(3) 0.036(3) 0.042(3) -0.007(2) 0.020(2) 0.005(2) C17A 0.038(3) 0.041(3) 0.057(3) 0.012(2) 0.023(2) 0.026(2) O1A 0.0225(16) 0.0342(19) 0.057(2) 0.0073(15) 0.0165(14) 0.0149(14) C17B 0.027(18) 0.022(13) 0.03(2) 0.003(13) 0.022(15) 0.007(10) O1B 0.028(9) 0.033(10) 0.027(13) 0.003(9) 0.017(10) 0.021(8) O2 0.0266(14) 0.0313(16) 0.0376(15) -0.0001(12) 0.0167(12) 0.0080(12) O3 0.0347(15) 0.0367(17) 0.0278(14) 0.0007(13) 0.0094(12) 0.0023(13) N4 0.0245(18) 0.037(2) 0.042(2) -0.0021(16) 0.0143(15) 0.0091(15) S1 0.0249(5) 0.0319(6) 0.0349(6) -0.0054(4) 0.0140(4) 0.0072(4) _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 N1 C2 1.364(5) . ? N1 C7A 1.383(5) . ? N1 H1 0.86(4) . ? C2 N3 1.317(5) . ? C2 S1 1.766(4) . ? N3 C3A 1.382(5) . ? C3A C4 1.399(5) . ? C3A C7A 1.400(5) . ? C4 C5 1.379(6) . ? C4 H4 0.9500 . ? C5 C6 1.406(6) . ? C5 O1B 1.45(3) . ? C5 H5 1.07(5) . ? C6 O1A 1.362(4) . ? C6 C7 1.396(5) . ? C7 C7A 1.399(5) . ? C7 H7 0.9500 . ? C8 C9 1.514(5) . ? C8 S1 1.803(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N4 1.347(5) . ? C9 C10 1.385(5) . ? C10 C11 1.387(5) . ? C10 C14 1.514(5) . ? C11 C12 1.385(6) . ? C11 O3 1.390(5) . ? C12 C13 1.381(6) . ? C12 C15 1.514(5) . ? C13 N4 1.334(5) . ? C13 H13 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 O3 1.416(5) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17A O1A 1.427(5) . ? C17A H17A 0.9800 . ? C17A H17B 0.9800 . ? C17A H17C 0.9800 . ? C17B O1B 1.40(5) . ? C17B H5 0.95(5) . ? C17B H17D 0.9800 . ? C17B H17E 0.9800 . ? C17B H17F 0.9800 . ? O1B H5 0.83(4) . ? O2 S1 1.506(3) . ? 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 N1 C7A 105.4(4) . . ? C2 N1 H1 123(3) . . ? C7A N1 H1 130(3) . . ? N3 C2 N1 114.8(3) . . ? N3 C2 S1 119.9(3) . . ? N1 C2 S1 125.3(3) . . ? C2 N3 C3A 103.6(3) . . ? N3 C3A C4 129.4(4) . . ? N3 C3A C7A 110.6(3) . . ? C4 C3A C7A 119.9(4) . . ? C5 C4 C3A 118.0(4) . . ? C5 C4 H4 121.0 . . ? C3A C4 H4 121.0 . . ? C4 C5 C6 120.6(4) . . ? C4 C5 O1B 156.2(11) . . ? C6 C5 O1B 83.1(11) . . ? C4 C5 H5 122(3) . . ? C6 C5 H5 118(3) . . ? O1B C5 H5 35(2) . . ? O1A C6 C7 123.1(4) . . ? O1A C6 C5 113.4(4) . . ? C7 C6 C5 123.5(4) . . ? C6 C7 C7A 114.1(4) . . ? C6 C7 H7 123.0 . . ? C7A C7 H7 123.0 . . ? N1 C7A C7 130.5(4) . . ? N1 C7A C3A 105.5(3) . . ? C7 C7A C3A 123.9(4) . . ? C9 C8 S1 109.8(2) . . ? C9 C8 H8A 109.7 . . ? S1 C8 H8A 109.7 . . ? C9 C8 H8B 109.7 . . ? S1 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? N4 C9 C10 123.8(3) . . ? N4 C9 C8 114.1(3) . . ? C10 C9 C8 122.0(3) . . ? C9 C10 C11 116.6(4) . . ? C9 C10 C14 122.9(3) . . ? C11 C10 C14 120.5(4) . . ? C12 C11 C10 121.4(4) . . ? C12 C11 O3 119.6(3) . . ? C10 C11 O3 118.9(4) . . ? C13 C12 C11 116.5(3) . . ? C13 C12 C15 120.8(4) . . ? C11 C12 C15 122.7(4) . . ? N4 C13 C12 124.5(4) . . ? N4 C13 H13 117.8 . . ? C12 C13 H13 117.8 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? 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 . . ? O3 C16 H16A 109.5 . . ? O3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C6 O1A C17A 115.9(3) . . ? O1B C17B H5 35(3) . . ? O1B C17B H17D 109.5 . . ? H5 C17B H17D 83.6 . . ? O1B C17B H17E 109.5 . . ? H5 C17B H17E 143.2 . . ? H17D C17B H17E 109.5 . . ? O1B C17B H17F 109.5 . . ? H5 C17B H17F 97.2 . . ? H17D C17B H17F 109.5 . . ? H17E C17B H17F 109.5 . . ? C17B O1B C5 89(2) . . ? C17B O1B H5 42(4) . . ? C5 O1B H5 47(4) . . ? C11 O3 C16 113.1(3) . . ? C13 N4 C9 117.1(4) . . ? O2 S1 C2 107.18(17) . . ? O2 S1 C8 105.63(18) . . ? C2 S1 C8 96.87(17) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.10 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.371 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.070 #===END data_grd453_IV _database_code_depnum_ccdc_archive 'CCDC 633385' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6-methoxy-2-{(4-methoxy-3,5-dimethyl-2-pyridinyl)methylsulfinyl} -1H-benzimidazole ; _chemical_name_common ; 6-methoxy-2-((4-methoxy-3,5-dimethyl-2- pyridinyl)methylsulfinyl) -1H-benzimidazole ; _chemical_melting_point 156 _chemical_formula_moiety 'C17 H19 N3 O3 S' _chemical_formula_sum 'C17 H19 N3 O3 S' _chemical_formula_weight 345 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_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6439(16) _cell_length_b 10.2621(17) _cell_length_c 10.3322(17) _cell_angle_alpha 90.216(2) _cell_angle_beta 111.762(2) _cell_angle_gamma 116.113(2) _cell_volume 835.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4928 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 26.04 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 0.214 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8968 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _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 2.17 _diffrn_reflns_theta_max 26.06 _reflns_number_total 3280 _reflns_number_gt 2917 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0649P)^2^+0.6500P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3280 _refine_ls_number_parameters 249 _refine_ls_number_restraints 39 _refine_ls_R_factor_all 0.0565 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1329 _refine_ls_wR_factor_gt 0.1288 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.060 _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 N1 N 0.7325(2) 0.2418(2) 0.5659(2) 0.0314(4) Uani 1 1 d . . . H1 H 0.710(3) 0.162(3) 0.522(3) 0.028(6) Uiso 1 1 d . . . C2 C 0.6293(3) 0.2846(2) 0.5911(2) 0.0320(5) Uani 1 1 d . . . N3 N 0.7045(2) 0.4221(2) 0.65978(19) 0.0355(4) Uani 1 1 d . . . C3A C 0.8713(3) 0.4751(2) 0.6793(2) 0.0337(5) Uani 1 1 d . . . C4 C 1.0099(3) 0.6185(2) 0.7407(2) 0.0379(5) Uani 1 1 d . A . H4 H 0.9982 0.6954 0.7792 0.045 Uiso 1 1 calc R . . C5 C 1.1620(3) 0.6424(3) 0.7427(3) 0.0388(5) Uani 1 1 d U . . H5 H 1.261(4) 0.739(4) 0.783(3) 0.036(8) Uiso 0.88 1 d P . . C6 C 1.1808(3) 0.5296(3) 0.6871(2) 0.0370(5) Uani 1 1 d U A . C7 C 1.0459(3) 0.3862(2) 0.6250(2) 0.0335(5) Uani 1 1 d . . . H7 H 1.0585 0.3096 0.5871 0.040 Uiso 1 1 calc R A . C7A C 0.8916(3) 0.3643(2) 0.6228(2) 0.0320(5) Uani 1 1 d . A . C8 C 0.3471(3) 0.1243(2) 0.3537(2) 0.0344(5) Uani 1 1 d . . . H8A H 0.3803 0.2160 0.3151 0.041 Uiso 1 1 calc R . . H8B H 0.4055 0.0719 0.3363 0.041 Uiso 1 1 calc R . . C9 C 0.1566(3) 0.0263(2) 0.2804(2) 0.0303(5) Uani 1 1 d . . . C10 C 0.0838(3) -0.0825(2) 0.1593(2) 0.0309(5) Uani 1 1 d . . . C11 C -0.0935(3) -0.1578(2) 0.0933(2) 0.0337(5) Uani 1 1 d . . . C12 C -0.1905(3) -0.1270(3) 0.1478(2) 0.0379(5) Uani 1 1 d . . . C13 C -0.1018(3) -0.0204(3) 0.2722(3) 0.0403(5) Uani 1 1 d . . . H13 H -0.1654 -0.0005 0.3134 0.048 Uiso 1 1 calc R . . C14 C 0.1876(3) -0.1174(3) 0.1004(2) 0.0416(6) Uani 1 1 d . . . H14A H 0.2846 -0.0251 0.1052 0.062 Uiso 1 1 calc R . . H14B H 0.1171 -0.1699 0.0011 0.062 Uiso 1 1 calc R . . H14C H 0.2285 -0.1800 0.1564 0.062 Uiso 1 1 calc R . . C15 C -0.3822(3) -0.2020(4) 0.0746(3) 0.0571(8) Uani 1 1 d . . . H15A H -0.4287 -0.3055 0.0855 0.086 Uiso 1 1 calc R . . H15B H -0.4177 -0.1984 -0.0267 0.086 Uiso 1 1 calc R . . H15C H -0.4243 -0.1507 0.1177 0.086 Uiso 1 1 calc R . . C16 C -0.2150(4) -0.4072(3) -0.0112(3) 0.0526(7) Uani 1 1 d . . . H16A H -0.2957 -0.4390 0.0329 0.079 Uiso 1 1 calc R . . H16B H -0.1119 -0.4106 0.0509 0.079 Uiso 1 1 calc R . . H16C H -0.2665 -0.4734 -0.1033 0.079 Uiso 1 1 calc R . . C17A C 1.3684(3) 0.4591(3) 0.6497(3) 0.0380(6) Uani 0.887(4) 1 d PU A 1 H17A H 1.3378 0.3778 0.7004 0.057 Uiso 0.887(4) 1 calc PR A 1 H17B H 1.4884 0.5004 0.6679 0.057 Uiso 0.887(4) 1 calc PR A 1 H17C H 1.2982 0.4218 0.5474 0.057 Uiso 0.887(4) 1 calc PR A 1 O1A O 1.3403(2) 0.57209(18) 0.6983(2) 0.0349(5) Uani 0.887(4) 1 d PU A 1 C17B C 1.345(3) 0.851(2) 0.843(3) 0.047(5) Uani 0.113(4) 1 d PU A 2 H17D H 1.2640 0.8781 0.7749 0.070 Uiso 0.113(4) 1 calc PR A 2 H17E H 1.4592 0.9358 0.8788 0.070 Uiso 0.113(4) 1 calc PR A 2 H17F H 1.3130 0.8231 0.9220 0.070 Uiso 0.113(4) 1 calc PR A 2 O1B O 1.3422(18) 0.7312(16) 0.7742(15) 0.039(4) Uani 0.113(4) 1 d PU A 2 O2 O 0.38880(18) 0.02925(16) 0.59652(16) 0.0333(4) Uani 1 1 d . . . O3 O -0.1730(2) -0.25965(17) -0.03203(16) 0.0404(4) Uani 1 1 d . . . N4 N 0.0672(2) 0.0558(2) 0.3374(2) 0.0361(4) Uani 1 1 d . . . S1 S 0.40898(6) 0.17015(6) 0.54314(6) 0.03161(18) Uani 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 N1 0.0239(9) 0.0248(9) 0.0295(9) -0.0003(7) 0.0078(7) 0.0013(7) C2 0.0227(10) 0.0302(11) 0.0262(11) -0.0013(8) 0.0067(8) 0.0018(9) N3 0.0265(9) 0.0323(10) 0.0280(9) -0.0042(7) 0.0060(8) 0.0024(8) C3A 0.0279(11) 0.0302(11) 0.0251(11) 0.0000(8) 0.0049(9) 0.0043(9) C4 0.0305(11) 0.0300(11) 0.0313(12) -0.0020(9) 0.0038(9) 0.0039(9) C5 0.0277(11) 0.0299(11) 0.0341(12) 0.0027(9) 0.0017(9) 0.0027(10) C6 0.0197(10) 0.0408(12) 0.0350(12) 0.0154(10) 0.0053(9) 0.0066(9) C7 0.0271(11) 0.0312(11) 0.0309(11) 0.0081(9) 0.0078(9) 0.0082(9) C7A 0.0224(10) 0.0305(11) 0.0253(10) 0.0059(8) 0.0049(8) 0.0020(9) C8 0.0244(11) 0.0327(11) 0.0274(11) -0.0020(9) 0.0091(9) -0.0003(9) C9 0.0236(10) 0.0267(10) 0.0285(11) 0.0045(8) 0.0083(9) 0.0041(8) C10 0.0260(10) 0.0281(10) 0.0253(10) 0.0065(8) 0.0085(8) 0.0038(9) C11 0.0291(11) 0.0283(10) 0.0238(10) 0.0060(8) 0.0063(9) 0.0012(9) C12 0.0232(11) 0.0384(12) 0.0345(12) 0.0073(10) 0.0073(9) 0.0041(9) C13 0.0294(12) 0.0421(13) 0.0431(14) 0.0063(11) 0.0154(10) 0.0115(10) C14 0.0345(12) 0.0457(13) 0.0289(12) -0.0029(10) 0.0114(10) 0.0079(11) C15 0.0256(12) 0.0657(18) 0.0529(16) 0.0052(14) 0.0092(12) 0.0054(12) C16 0.0584(17) 0.0340(13) 0.0312(13) -0.0052(10) 0.0117(12) -0.0001(12) C17A 0.0277(13) 0.0353(13) 0.0503(16) 0.0101(12) 0.0147(12) 0.0155(11) O1A 0.0198(8) 0.0281(9) 0.0492(11) 0.0056(8) 0.0101(8) 0.0085(7) C17B 0.030(10) 0.027(8) 0.061(14) 0.008(8) 0.009(9) 0.003(7) O1B 0.023(6) 0.040(7) 0.038(8) 0.002(6) 0.009(6) 0.005(5) O2 0.0259(7) 0.0315(8) 0.0324(8) 0.0004(6) 0.0125(6) 0.0049(6) O3 0.0331(8) 0.0357(8) 0.0232(8) 0.0015(6) 0.0048(6) -0.0020(7) N4 0.0272(9) 0.0319(10) 0.0368(11) 0.0008(8) 0.0114(8) 0.0055(8) S1 0.0227(3) 0.0285(3) 0.0292(3) -0.0037(2) 0.0086(2) 0.0023(2) _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 N1 C2 1.352(3) . ? N1 C7A 1.381(3) . ? N1 H1 0.83(2) . ? C2 N3 1.316(3) . ? C2 S1 1.777(2) . ? N3 C3A 1.383(3) . ? C3A C7A 1.396(3) . ? C3A C4 1.409(3) . ? C4 C5 1.368(4) . ? C4 H4 0.9500 . ? C5 C6 1.400(4) . ? C5 O1B 1.463(14) . ? C5 H5 0.97(3) . ? C6 O1A 1.359(3) . ? C6 C7 1.399(3) . ? C7 C7A 1.395(3) . ? C7 H7 0.9500 . ? C8 C9 1.516(3) . ? C8 S1 1.813(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N4 1.336(3) . ? C9 C10 1.397(3) . ? C10 C11 1.398(3) . ? C10 C14 1.506(3) . ? C11 O3 1.380(3) . ? C11 C12 1.394(3) . ? C12 C13 1.389(3) . ? C12 C15 1.512(3) . ? C13 N4 1.335(3) . ? C13 H13 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 O3 1.424(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17A O1A 1.429(3) . ? C17A H17A 0.9800 . ? C17A H17B 0.9800 . ? C17A H17C 0.9800 . ? C17B O1B 1.40(3) . ? C17B H5 1.08(4) . ? C17B H17D 0.9800 . ? C17B H17E 0.9800 . ? C17B H17F 0.9800 . ? O1B H5 0.86(3) . ? O2 S1 1.5069(16) . ? 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 N1 C7A 105.54(19) . . ? C2 N1 H1 129.8(17) . . ? C7A N1 H1 124.6(17) . . ? N3 C2 N1 114.95(19) . . ? N3 C2 S1 119.68(18) . . ? N1 C2 S1 125.35(16) . . ? C2 N3 C3A 103.52(19) . . ? N3 C3A C7A 110.38(18) . . ? N3 C3A C4 129.4(2) . . ? C7A C3A C4 120.2(2) . . ? C5 C4 C3A 117.3(2) . . ? C5 C4 H4 121.3 . . ? C3A C4 H4 121.3 . . ? C4 C5 C6 121.8(2) . . ? C4 C5 O1B 154.8(7) . . ? C6 C5 O1B 83.4(7) . . ? C4 C5 H5 120(2) . . ? C6 C5 H5 118(2) . . ? O1B C5 H5 34.6(19) . . ? O1A C6 C7 123.4(2) . . ? O1A C6 C5 114.1(2) . . ? C7 C6 C5 122.5(2) . . ? C7A C7 C6 114.9(2) . . ? C7A C7 H7 122.5 . . ? C6 C7 H7 122.5 . . ? N1 C7A C7 131.1(2) . . ? N1 C7A C3A 105.60(19) . . ? C7 C7A C3A 123.3(2) . . ? C9 C8 S1 109.08(15) . . ? C9 C8 H8A 109.9 . . ? S1 C8 H8A 109.9 . . ? C9 C8 H8B 109.9 . . ? S1 C8 H8B 109.9 . . ? H8A C8 H8B 108.3 . . ? N4 C9 C10 123.94(19) . . ? N4 C9 C8 115.08(19) . . ? C10 C9 C8 121.0(2) . . ? C9 C10 C11 116.1(2) . . ? C9 C10 C14 122.89(19) . . ? C11 C10 C14 121.0(2) . . ? O3 C11 C12 119.66(19) . . ? O3 C11 C10 118.9(2) . . ? C12 C11 C10 121.3(2) . . ? C13 C12 C11 116.5(2) . . ? C13 C12 C15 121.2(2) . . ? C11 C12 C15 122.3(2) . . ? N4 C13 C12 124.0(2) . . ? N4 C13 H13 118.0 . . ? C12 C13 H13 118.0 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? 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 . . ? O3 C16 H16A 109.5 . . ? O3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C6 O1A C17A 116.36(19) . . ? O1B C17B H5 38.0(19) . . ? O1B C17B H17D 109.5 . . ? H5 C17B H17D 86.6 . . ? O1B C17B H17E 109.5 . . ? H5 C17B H17E 147.3 . . ? H17D C17B H17E 109.5 . . ? O1B C17B H17F 109.5 . . ? H5 C17B H17F 90.3 . . ? H17D C17B H17F 109.5 . . ? H17E C17B H17F 109.5 . . ? C17B O1B C5 89.5(13) . . ? C17B O1B H5 50(3) . . ? C5 O1B H5 40(2) . . ? C11 O3 C16 113.30(17) . . ? C13 N4 C9 117.9(2) . . ? O2 S1 C2 107.02(10) . . ? O2 S1 C8 105.53(10) . . ? C2 S1 C8 96.79(10) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.06 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.591 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.060 #===END data_grd614_V _database_code_depnum_ccdc_archive 'CCDC 633386' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5(6)-methoxy-2-{(4-methoxy-3,5-dimethyl-2-pyridinyl)methylsulfinyl} -1H-benzimidazole ; _chemical_name_common ; 5(6)-methoxy-2-((4-methoxy-3,5-dimethyl-2- pyridinyl)methylsulfinyl) -1H-benzimidazole ; _chemical_melting_point 156 _chemical_formula_moiety 'C17 H19 N3 O3 S' _chemical_formula_sum 'C17 H19 N3 O3 S' _chemical_formula_weight 345 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_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.701(3) _cell_length_b 10.259(3) _cell_length_c 10.694(3) _cell_angle_alpha 91.720(4) _cell_angle_beta 112.117(4) _cell_angle_gamma 115.642(4) _cell_volume 864.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2547 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 25.88 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 0.207 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8775 _diffrn_reflns_av_R_equivalents 0.0520 _diffrn_reflns_av_sigmaI/netI 0.0750 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 26.07 _reflns_number_total 3373 _reflns_number_gt 1736 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0844P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3373 _refine_ls_number_parameters 249 _refine_ls_number_restraints 39 _refine_ls_R_factor_all 0.1301 _refine_ls_R_factor_gt 0.0611 _refine_ls_wR_factor_ref 0.1666 _refine_ls_wR_factor_gt 0.1410 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.982 _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 N1 N 0.7327(3) 0.2447(3) 0.5667(3) 0.0642(8) Uani 1 1 d . . . H1 H 0.704(4) 0.159(3) 0.520(3) 0.058(10) Uiso 1 1 d . . . C2 C 0.6319(4) 0.2902(4) 0.5915(3) 0.0635(9) Uani 1 1 d . . . N3 N 0.7090(3) 0.4294(3) 0.6593(3) 0.0701(9) Uani 1 1 d . . . C3A C 0.8735(4) 0.4808(4) 0.6773(3) 0.0632(9) Uani 1 1 d . . . C4 C 1.0139(4) 0.6230(4) 0.7389(4) 0.0777(11) Uani 1 1 d . A . H4 H 1.0042 0.6999 0.7763 0.093 Uiso 1 1 calc R . . C5 C 1.1638(5) 0.6459(5) 0.7428(4) 0.0791(11) Uani 1 1 d U . . H5 H 1.270(6) 0.757(6) 0.776(5) 0.070(13) Uiso 0.85 1 d P . . C6 C 1.1797(4) 0.5312(4) 0.6865(4) 0.0695(10) Uani 1 1 d U A . C7 C 1.0448(4) 0.3864(4) 0.6245(3) 0.0675(10) Uani 1 1 d . . . H7 H 1.0552 0.3095 0.5879 0.081 Uiso 1 1 calc R A . C7A C 0.8928(4) 0.3691(4) 0.6231(3) 0.0591(9) Uani 1 1 d . A . C8 C 0.3475(4) 0.1315(4) 0.3605(3) 0.0761(11) Uani 1 1 d . . . H8A H 0.3773 0.2224 0.3274 0.091 Uiso 1 1 calc R . . H8B H 0.4060 0.0830 0.3410 0.091 Uiso 1 1 calc R . . C9 C 0.1570(4) 0.0297(4) 0.2854(3) 0.0618(9) Uani 1 1 d . . . C10 C 0.0854(4) -0.0756(4) 0.1652(3) 0.0644(9) Uani 1 1 d . . . C11 C -0.0909(4) -0.1562(4) 0.1014(3) 0.0712(10) Uani 1 1 d . . . C12 C -0.1877(4) -0.1322(4) 0.1566(4) 0.0769(11) Uani 1 1 d . . . C13 C -0.0983(4) -0.0266(4) 0.2797(4) 0.0822(11) Uani 1 1 d . . . H13 H -0.1609 -0.0105 0.3203 0.099 Uiso 1 1 calc R . . C14 C 0.1897(5) -0.1036(5) 0.1037(4) 0.0917(13) Uani 1 1 d . . . H14A H 0.2669 -0.0115 0.0934 0.138 Uiso 1 1 calc R . . H14B H 0.1160 -0.1716 0.0146 0.138 Uiso 1 1 calc R . . H14C H 0.2526 -0.1455 0.1641 0.138 Uiso 1 1 calc R . . C15 C -0.3795(4) -0.2115(6) 0.0870(5) 0.1290(19) Uani 1 1 d . . . H15A H -0.4184 -0.2130 -0.0102 0.193 Uiso 1 1 calc R . . H15B H -0.4201 -0.1601 0.1280 0.193 Uiso 1 1 calc R . . H15C H -0.4215 -0.3115 0.0991 0.193 Uiso 1 1 calc R . . C16 C -0.2063(7) -0.4052(5) -0.0107(5) 0.135(2) Uani 1 1 d . . . H16A H -0.1037 -0.4060 0.0482 0.203 Uiso 1 1 calc R . . H16B H -0.2543 -0.4678 -0.1007 0.203 Uiso 1 1 calc R . . H16C H -0.2857 -0.4416 0.0291 0.203 Uiso 1 1 calc R . . C17A C 1.3647(5) 0.4615(5) 0.6510(5) 0.0829(14) Uani 0.854(3) 1 d PU A 1 H17A H 1.3386 0.3836 0.6996 0.124 Uiso 0.854(3) 1 calc PR A 1 H17B H 1.4812 0.5030 0.6671 0.124 Uiso 0.854(3) 1 calc PR A 1 H17C H 1.2930 0.4217 0.5534 0.124 Uiso 0.854(3) 1 calc PR A 1 O1A O 1.3373(3) 0.5729(3) 0.6991(3) 0.0784(10) Uani 0.854(3) 1 d PU A 1 C17B C 1.343(3) 0.857(3) 0.835(3) 0.085(8) Uani 0.146(3) 1 d PU A 2 H17D H 1.2690 0.8827 0.7637 0.128 Uiso 0.146(3) 1 calc PR A 2 H17E H 1.4554 0.9398 0.8757 0.128 Uiso 0.146(3) 1 calc PR A 2 H17F H 1.3024 0.8341 0.9052 0.128 Uiso 0.146(3) 1 calc PR A 2 O1B O 1.3438(19) 0.7289(17) 0.7752(16) 0.065(4) Uani 0.146(3) 1 d PU A 2 O2 O 0.3924(2) 0.0340(2) 0.5906(2) 0.0687(7) Uani 1 1 d . . . O3 O -0.1694(3) -0.2577(3) -0.0236(2) 0.0927(9) Uani 1 1 d . . . N4 N 0.0687(3) 0.0539(3) 0.3452(3) 0.0737(9) Uani 1 1 d . . . S1 S 0.41240(10) 0.17500(10) 0.54412(9) 0.0669(4) Uani 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 N1 0.0506(17) 0.0504(18) 0.0609(19) -0.0054(15) 0.0198(14) 0.0037(14) C2 0.0434(18) 0.063(2) 0.055(2) -0.0036(17) 0.0172(16) 0.0060(16) N3 0.0486(16) 0.0644(18) 0.0592(18) -0.0126(14) 0.0161(14) 0.0035(13) C3A 0.0514(19) 0.056(2) 0.049(2) -0.0057(16) 0.0111(16) 0.0076(16) C4 0.059(2) 0.063(2) 0.064(2) -0.0113(18) 0.0099(18) 0.0054(17) C5 0.051(2) 0.063(2) 0.075(3) -0.002(2) 0.0073(19) 0.0045(18) C6 0.0374(17) 0.077(2) 0.063(2) 0.0228(19) 0.0097(16) 0.0116(16) C7 0.053(2) 0.065(2) 0.062(2) 0.0160(17) 0.0151(17) 0.0183(17) C7A 0.0416(17) 0.062(2) 0.0450(19) 0.0065(16) 0.0120(14) 0.0068(15) C8 0.0474(18) 0.078(2) 0.063(2) 0.0021(18) 0.0223(17) 0.0001(17) C9 0.0451(17) 0.060(2) 0.056(2) 0.0106(17) 0.0190(16) 0.0084(15) C10 0.0509(19) 0.070(2) 0.049(2) 0.0118(17) 0.0195(16) 0.0119(16) C11 0.054(2) 0.069(2) 0.047(2) 0.0114(18) 0.0098(17) 0.0037(17) C12 0.0437(19) 0.088(3) 0.065(2) 0.018(2) 0.0155(19) 0.0100(18) C13 0.055(2) 0.090(3) 0.091(3) 0.019(2) 0.037(2) 0.022(2) C14 0.071(2) 0.118(3) 0.062(2) 0.001(2) 0.028(2) 0.027(2) C15 0.041(2) 0.169(5) 0.108(3) 0.032(3) 0.017(2) 0.007(2) C16 0.151(5) 0.087(3) 0.078(3) -0.014(3) 0.036(3) -0.003(3) C17A 0.065(3) 0.081(3) 0.117(4) 0.033(3) 0.043(3) 0.043(2) O1A 0.0412(15) 0.0692(19) 0.108(2) 0.0096(16) 0.0227(15) 0.0210(13) C17B 0.080(17) 0.046(10) 0.11(2) 0.004(13) 0.043(15) 0.015(9) O1B 0.051(7) 0.068(8) 0.077(11) 0.009(7) 0.029(8) 0.029(6) O2 0.0572(13) 0.0612(14) 0.0739(16) 0.0052(12) 0.0352(12) 0.0118(11) O3 0.0766(16) 0.0908(19) 0.0479(15) 0.0039(14) 0.0136(13) 0.0004(14) N4 0.0523(17) 0.0684(19) 0.081(2) 0.0021(16) 0.0286(16) 0.0138(14) S1 0.0453(5) 0.0616(6) 0.0651(6) -0.0102(4) 0.0236(4) 0.0037(4) _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 N1 C2 1.352(4) . ? N1 C7A 1.391(4) . ? N1 H1 0.87(3) . ? C2 N3 1.316(4) . ? C2 S1 1.778(3) . ? N3 C3A 1.377(4) . ? C3A C7A 1.383(4) . ? C3A C4 1.401(4) . ? C4 C5 1.353(5) . ? C4 H4 0.9300 . ? C5 C6 1.398(5) . ? C5 O1B 1.461(16) . ? C5 H5 1.08(5) . ? C6 O1A 1.347(4) . ? C6 C7 1.401(4) . ? C7 C7A 1.401(4) . ? C7 H7 0.9300 . ? C8 C9 1.520(4) . ? C8 S1 1.796(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N4 1.339(4) . ? C9 C10 1.377(4) . ? C10 C11 1.392(4) . ? C10 C14 1.510(5) . ? C11 C12 1.378(5) . ? C11 O3 1.383(4) . ? C12 C13 1.379(5) . ? C12 C15 1.513(5) . ? C13 N4 1.323(4) . ? C13 H13 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 O3 1.421(5) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17A O1A 1.403(5) . ? C17A H17A 0.9600 . ? C17A H17B 0.9600 . ? C17A H17C 0.9600 . ? C17B O1B 1.45(3) . ? C17B H5 0.98(4) . ? C17B H17D 0.9600 . ? C17B H17E 0.9600 . ? C17B H17F 0.9600 . ? O1B H5 0.88(4) . ? O2 S1 1.500(2) . ? 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 N1 C7A 105.1(3) . . ? C2 N1 H1 128(2) . . ? C7A N1 H1 127(2) . . ? N3 C2 N1 115.0(3) . . ? N3 C2 S1 120.2(3) . . ? N1 C2 S1 124.8(2) . . ? C2 N3 C3A 103.4(3) . . ? N3 C3A C7A 111.0(3) . . ? N3 C3A C4 129.9(3) . . ? C7A C3A C4 119.1(3) . . ? C5 C4 C3A 118.5(4) . . ? C5 C4 H4 120.7 . . ? C3A C4 H4 120.7 . . ? C4 C5 C6 121.2(3) . . ? C4 C5 O1B 157.1(8) . . ? C6 C5 O1B 81.7(7) . . ? C4 C5 H5 121(3) . . ? C6 C5 H5 117(2) . . ? O1B C5 H5 37(2) . . ? O1A C6 C5 113.6(3) . . ? O1A C6 C7 123.3(4) . . ? C5 C6 C7 123.1(3) . . ? C7A C7 C6 113.2(4) . . ? C7A C7 H7 123.4 . . ? C6 C7 H7 123.4 . . ? C3A C7A N1 105.5(3) . . ? C3A C7A C7 124.8(3) . . ? N1 C7A C7 129.7(3) . . ? C9 C8 S1 110.0(2) . . ? C9 C8 H8A 109.7 . . ? S1 C8 H8A 109.7 . . ? C9 C8 H8B 109.7 . . ? S1 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? N4 C9 C10 124.2(3) . . ? N4 C9 C8 114.2(3) . . ? C10 C9 C8 121.6(3) . . ? C9 C10 C11 116.4(3) . . ? C9 C10 C14 122.7(3) . . ? C11 C10 C14 120.9(3) . . ? C12 C11 O3 119.8(3) . . ? C12 C11 C10 121.6(3) . . ? O3 C11 C10 118.6(3) . . ? C11 C12 C13 115.6(3) . . ? C11 C12 C15 123.3(4) . . ? C13 C12 C15 121.0(4) . . ? N4 C13 C12 125.7(3) . . ? N4 C13 H13 117.2 . . ? C12 C13 H13 117.2 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? 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 . . ? O3 C16 H16A 109.5 . . ? O3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C6 O1A C17A 116.7(3) . . ? O1B C17B H5 36(3) . . ? O1B C17B H17D 109.5 . . ? H5 C17B H17D 84.9 . . ? O1B C17B H17E 109.5 . . ? H5 C17B H17E 144.6 . . ? H17D C17B H17E 109.5 . . ? O1B C17B H17F 109.5 . . ? H5 C17B H17F 94.7 . . ? H17D C17B H17F 109.5 . . ? H17E C17B H17F 109.5 . . ? C17B O1B C5 86.8(14) . . ? C17B O1B H5 41(4) . . ? C5 O1B H5 47(4) . . ? C11 O3 C16 114.2(3) . . ? C13 N4 C9 116.4(3) . . ? O2 S1 C2 107.35(15) . . ? O2 S1 C8 106.05(16) . . ? C2 S1 C8 96.46(15) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.07 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.255 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.045