#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2206649.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2206649 loop_ _publ_author_name 'Akkurt, Mehmet' 'Karaca, Selvi' 'K\"u\,c\"ukbay, Hasan' 'Y\?ilmaz, \"Ulk\"u' 'B\"uy\"ukg\"ung\"or, Orhan' _publ_section_title ; Mercapto-N-phenylformimidoyl-1-ethyl-3-(2-morpholinoethyl)benzimidazolinium inner salt ; _journal_coeditor_code CF6448 _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o2875 _journal_page_last o2877 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C22 H26 N4 O S' _chemical_formula_moiety 'C22 H26 N4 O S' _chemical_formula_sum 'C22 H26 N4 O S' _chemical_formula_weight 394.54 _chemical_name_common ; Mercapto-N-phenylformimidoyl-1-ethyl-3-(2-morpholinoethyl)benzimidazoliniuum inner salt ; _chemical_name_systematic ; [1-ethyl-3-(2-morpholinoethyl)benzimidazolio](phenylimino)methanethiolate ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 105.927(12) _cell_angle_beta 91.443(13) _cell_angle_gamma 110.871(14) _cell_formula_units_Z 2 _cell_length_a 8.9037(16) _cell_length_b 9.1916(15) _cell_length_c 13.950(2) _cell_measurement_reflns_used 7037 _cell_measurement_temperature 100 _cell_measurement_theta_max 27.13 _cell_measurement_theta_min 2.47 _cell_volume 1016.1(3) _computing_cell_refinement X-AREA _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED32 (Stoe & Cie, 2002)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 0.805 _diffrn_measured_fraction_theta_max 0.805 _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'Stoe IPDS-II' _diffrn_measurement_method \w _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1103 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 4337 _diffrn_reflns_reduction_process ' ?' _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_min 2.47 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.180 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_correction_T_min 0.909 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details '(XABS2; Parkin et al., 1968)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description plate _exptl_crystal_F_000 420 _exptl_crystal_size_max 0.540 _exptl_crystal_size_mid 0.363 _exptl_crystal_size_min 0.110 _refine_diff_density_max 0.306 _refine_diff_density_min -0.274 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 254 _refine_ls_number_reflns 3213 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.012 _refine_ls_R_factor_all 0.1294 _refine_ls_R_factor_gt 0.0741 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0925P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1548 _refine_ls_wR_factor_ref 0.1834 _reflns_number_gt 1957 _reflns_number_total 3213 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cf6448.cif _[local]_cod_data_source_block 2 _cod_original_cell_volume 1016.2(3) _cod_database_code 2206649 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0408(6) 0.0305(5) 0.0475(8) 0.0089(4) 0.0009(5) 0.0175(4) O1 0.055(2) 0.0443(16) 0.049(2) 0.0210(16) 0.0130(16) 0.0113(15) N1 0.0364(19) 0.0242(15) 0.034(2) 0.0122(15) 0.0062(15) 0.0090(13) N2 0.045(2) 0.0239(15) 0.036(2) 0.0138(16) 0.0070(16) 0.0078(14) N3 0.042(2) 0.0323(16) 0.040(2) 0.0139(16) 0.0086(16) 0.0171(15) N4 0.046(2) 0.0273(16) 0.041(3) 0.0128(17) 0.0089(16) 0.0022(15) C1 0.037(2) 0.0277(18) 0.039(3) 0.0112(18) 0.0106(18) 0.0126(17) C2 0.044(3) 0.0264(18) 0.072(4) 0.0167(19) 0.020(2) 0.020(2) C3 0.049(3) 0.040(2) 0.072(4) 0.024(2) 0.022(2) 0.034(2) C4 0.048(3) 0.061(3) 0.076(4) 0.033(3) 0.025(3) 0.049(3) C5 0.038(2) 0.045(2) 0.044(3) 0.017(2) 0.0101(19) 0.023(2) C6 0.035(2) 0.0321(18) 0.031(3) 0.0164(17) 0.0114(16) 0.0184(16) C7 0.049(3) 0.0303(19) 0.030(3) 0.0190(19) 0.0051(18) 0.0025(16) C8 0.059(3) 0.053(3) 0.045(3) 0.030(3) 0.011(2) 0.001(2) C9 0.035(2) 0.0245(17) 0.023(3) 0.0073(16) 0.0012(15) 0.0053(14) C10 0.040(2) 0.0302(18) 0.026(2) 0.0179(17) 0.0094(17) 0.0079(15) C11 0.032(2) 0.0240(17) 0.043(3) 0.0059(17) 0.0006(18) 0.0120(16) C12 0.043(2) 0.038(2) 0.037(3) 0.016(2) 0.0029(19) 0.0141(18) C13 0.056(3) 0.041(2) 0.029(3) 0.017(2) 0.004(2) 0.0164(18) C14 0.043(3) 0.0264(18) 0.047(3) 0.0053(19) -0.011(2) 0.0099(17) C15 0.047(3) 0.037(2) 0.046(3) 0.020(2) 0.003(2) 0.0097(19) C16 0.043(3) 0.040(2) 0.041(3) 0.016(2) 0.0071(19) 0.0161(19) C17 0.044(2) 0.0273(18) 0.034(3) 0.0117(18) 0.0008(18) 0.0000(16) C18 0.049(3) 0.036(2) 0.039(3) 0.018(2) 0.008(2) 0.0051(18) C19 0.047(3) 0.0275(19) 0.049(3) 0.010(2) 0.008(2) 0.0037(18) C20 0.053(3) 0.038(2) 0.044(3) 0.021(2) 0.017(2) 0.0124(19) C21 0.048(3) 0.039(2) 0.045(3) 0.009(2) 0.006(2) -0.002(2) C22 0.058(3) 0.034(2) 0.044(3) 0.007(2) 0.013(2) 0.0087(19) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol S1 0.58227(14) 0.15510(12) 0.20438(10) 0.0398(4) Uani . . 1.000 S O1 0.2951(4) 0.8174(4) 0.4009(3) 0.0493(11) Uani . . 1.000 O N1 0.7125(4) 0.3833(3) 0.0430(3) 0.0313(10) Uani . . 1.000 N N2 0.7508(4) 0.5684(4) 0.1872(3) 0.0350(11) Uani . . 1.000 N N3 0.9120(4) 0.3331(4) 0.2212(3) 0.0368(11) Uani . . 1.000 N N4 0.5163(5) 0.6601(4) 0.3321(3) 0.0401(13) Uani . . 1.000 N C1 0.7293(5) 0.6373(4) 0.1140(3) 0.0342(13) Uani . . 1.000 C C2 0.7273(6) 0.7916(5) 0.1207(4) 0.0452(18) Uani . . 1.000 C C3 0.6991(6) 0.8172(6) 0.0295(4) 0.0477(18) Uani . . 1.000 C C4 0.6711(6) 0.6994(6) -0.0633(5) 0.0517(19) Uani . . 1.000 C C5 0.6744(5) 0.5462(5) -0.0701(4) 0.0398(14) Uani . . 1.000 C C6 0.7050(5) 0.5200(4) 0.0202(3) 0.0296(13) Uani . . 1.000 C C7 0.7010(5) 0.2300(5) -0.0351(3) 0.0367(15) Uani . . 1.000 C C8 0.8676(7) 0.2447(6) -0.0642(4) 0.0527(17) Uani . . 1.000 C C9 0.7406(5) 0.4144(4) 0.1401(3) 0.0291(13) Uani . . 1.000 C C10 0.7594(5) 0.2993(4) 0.1939(3) 0.0308(11) Uani . . 1.000 C C11 0.9562(5) 0.2461(4) 0.2799(4) 0.0340(13) Uani . . 1.000 C C12 0.9091(6) 0.2471(5) 0.3732(4) 0.0386(14) Uani . . 1.000 C C13 0.9691(6) 0.1738(5) 0.4316(4) 0.0412(16) Uani . . 1.000 C C14 1.0771(6) 0.1011(5) 0.3966(4) 0.0416(15) Uani . . 1.000 C C15 1.1250(6) 0.1005(5) 0.3035(4) 0.0428(16) Uani . . 1.000 C C16 1.0639(6) 0.1728(5) 0.2440(4) 0.0404(16) Uani . . 1.000 C C17 0.7882(5) 0.6482(5) 0.2957(3) 0.0377(13) Uani . . 1.000 C C18 0.6443(6) 0.6023(5) 0.3525(4) 0.0421(16) Uani . . 1.000 C C19 0.5701(6) 0.8378(5) 0.3751(4) 0.0440(15) Uani . . 1.000 C C20 0.4345(6) 0.8926(5) 0.3574(4) 0.0437(16) Uani . . 1.000 C C21 0.2435(6) 0.6451(5) 0.3607(4) 0.0493(16) Uani . . 1.000 C C22 0.3738(7) 0.5841(5) 0.3777(4) 0.0489(16) Uani . . 1.000 C H2 0.7438 0.8714 0.1821 0.054 Uiso calc R 1.00 H H3 0.6989 0.9187 0.0305 0.057 Uiso calc R 1.00 H H4 0.6499 0.7230 -0.1217 0.062 Uiso calc R 1.00 H H5 0.6571 0.4665 -0.1316 0.048 Uiso calc R 1.00 H H7A 0.6279 0.2107 -0.0940 0.044 Uiso calc R 1.00 H H7B 0.6575 0.1380 -0.0090 0.044 Uiso calc R 1.00 H H8A 0.9070 0.3309 -0.0944 0.079 Uiso calc R 1.00 H H8B 0.8604 0.1435 -0.1114 0.079 Uiso calc R 1.00 H H8C 0.9409 0.2689 -0.0052 0.079 Uiso calc R 1.00 H H12 0.8372 0.2967 0.3972 0.046 Uiso calc R 1.00 H H13 0.9364 0.1738 0.4944 0.050 Uiso calc R 1.00 H H14 1.1173 0.0526 0.4359 0.050 Uiso calc R 1.00 H H15 1.1981 0.0521 0.2801 0.052 Uiso calc R 1.00 H H16 1.0954 0.1717 0.1808 0.049 Uiso calc R 1.00 H H17A 0.8309 0.7656 0.3081 0.045 Uiso calc R 1.00 H H17B 0.8727 0.6204 0.3221 0.045 Uiso calc R 1.00 H H18A 0.5970 0.4842 0.3359 0.051 Uiso calc R 1.00 H H18B 0.6833 0.6459 0.4240 0.051 Uiso calc R 1.00 H H19A 0.6621 0.8909 0.3444 0.053 Uiso calc R 1.00 H H19B 0.6044 0.8691 0.4468 0.053 Uiso calc R 1.00 H H20A 0.4720 1.0103 0.3861 0.052 Uiso calc R 1.00 H H20B 0.4043 0.8658 0.2856 0.052 Uiso calc R 1.00 H H21A 0.2089 0.6131 0.2890 0.059 Uiso calc R 1.00 H H21B 0.1508 0.5938 0.3916 0.059 Uiso calc R 1.00 H H22A 0.4044 0.6097 0.4493 0.058 Uiso calc R 1.00 H H22B 0.3331 0.4663 0.3483 0.058 Uiso calc R 1.00 H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C20 O1 C21 108.9(4) yes C6 N1 C7 123.5(4) yes C6 N1 C9 110.2(3) yes C7 N1 C9 126.2(3) yes C1 N2 C9 107.8(4) yes C1 N2 C17 126.9(4) yes C9 N2 C17 125.2(4) yes C10 N3 C11 119.8(4) yes C18 N4 C19 111.4(4) yes C18 N4 C22 109.3(4) yes C19 N4 C22 108.1(4) yes N2 C1 C2 131.6(4) yes N2 C1 C6 107.5(3) yes C2 C1 C6 120.9(4) no C1 C2 C3 115.5(5) no C2 C3 C4 123.6(5) no C3 C4 C5 121.0(6) no C4 C5 C6 116.0(5) no N1 C6 C1 104.7(3) yes N1 C6 C5 132.1(4) yes C1 C6 C5 123.1(4) no N1 C7 C8 109.9(4) yes N1 C9 N2 109.7(3) yes N1 C9 C10 126.2(3) yes N2 C9 C10 124.1(4) yes S1 C10 N3 134.3(3) yes S1 C10 C9 114.9(3) yes N3 C10 C9 110.8(4) yes N3 C11 C12 122.4(4) yes N3 C11 C16 117.1(4) yes C12 C11 C16 120.2(4) no C11 C12 C13 120.0(5) no C12 C13 C14 120.3(5) no C13 C14 C15 119.9(5) no C14 C15 C16 120.1(5) no C11 C16 C15 119.6(5) no N2 C17 C18 114.2(4) yes N4 C18 C17 115.2(4) yes N4 C19 C20 110.2(4) yes O1 C20 C19 112.0(4) yes O1 C21 C22 112.7(4) yes N4 C22 C21 110.3(4) yes C1 C2 H2 122.0 no C3 C2 H2 122.0 no C2 C3 H3 118.0 no C4 C3 H3 118.0 no C3 C4 H4 120.0 no C5 C4 H4 120.0 no C4 C5 H5 122.0 no C6 C5 H5 122.0 no N1 C7 H7A 110.0 no N1 C7 H7B 110.0 no C8 C7 H7A 110.0 no C8 C7 H7B 110.0 no H7A C7 H7B 108.0 no C7 C8 H8A 110.0 no C7 C8 H8B 109.0 no C7 C8 H8C 109.0 no H8A C8 H8B 109.0 no H8A C8 H8C 109.0 no H8B C8 H8C 109.0 no C11 C12 H12 120.0 no C13 C12 H12 120.0 no C12 C13 H13 120.0 no C14 C13 H13 120.0 no C13 C14 H14 120.0 no C15 C14 H14 120.0 no C14 C15 H15 120.0 no C16 C15 H15 120.0 no C11 C16 H16 120.0 no C15 C16 H16 120.0 no N2 C17 H17A 109.0 no N2 C17 H17B 109.0 no C18 C17 H17A 109.0 no C18 C17 H17B 109.0 no H17A C17 H17B 108.0 no N4 C18 H18A 109.0 no N4 C18 H18B 109.0 no C17 C18 H18A 108.0 no C17 C18 H18B 108.0 no H18A C18 H18B 107.0 no N4 C19 H19A 110.0 no N4 C19 H19B 110.0 no C20 C19 H19A 110.0 no C20 C19 H19B 110.0 no H19A C19 H19B 108.0 no O1 C20 H20A 109.0 no O1 C20 H20B 109.0 no C19 C20 H20A 109.0 no C19 C20 H20B 109.0 no H20A C20 H20B 108.0 no O1 C21 H21A 109.0 no O1 C21 H21B 109.0 no C22 C21 H21A 109.0 no C22 C21 H21B 109.0 no H21A C21 H21B 108.0 no N4 C22 H22A 110.0 no N4 C22 H22B 110.0 no C21 C22 H22A 110.0 no C21 C22 H22B 110.0 no H22A C22 H22B 108.0 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 C10 1.701(4) yes O1 C20 1.430(6) yes O1 C21 1.420(6) yes N1 C6 1.401(5) yes N1 C7 1.494(6) yes N1 C9 1.303(6) yes N2 C1 1.383(5) yes N2 C9 1.356(5) yes N2 C17 1.460(6) yes N3 C10 1.302(6) yes N3 C11 1.426(6) yes N4 C18 1.470(7) yes N4 C19 1.465(6) yes N4 C22 1.468(7) yes C1 C2 1.402(6) no C1 C6 1.402(6) no C2 C3 1.388(7) no C3 C4 1.390(8) no C4 C5 1.396(7) no C5 C6 1.384(7) no C7 C8 1.517(8) no C9 C10 1.505(5) no C11 C12 1.376(7) no C11 C16 1.387(7) no C12 C13 1.392(7) no C13 C14 1.383(8) no C14 C15 1.376(7) no C15 C16 1.402(7) no C17 C18 1.516(7) no C19 C20 1.503(8) no C21 C22 1.496(8) no C2 H2 0.930 no C3 H3 0.930 no C4 H4 0.930 no C5 H5 0.930 no C7 H7A 0.970 no C7 H7B 0.970 no C8 H8A 0.960 no C8 H8B 0.960 no C8 H8C 0.960 no C12 H12 0.930 no C13 H13 0.930 no C14 H14 0.930 no C15 H15 0.930 no C16 H16 0.930 no C17 H17A 0.970 no C17 H17B 0.970 no C18 H18A 0.970 no C18 H18B 0.970 no C19 H19A 0.970 no C19 H19B 0.970 no C20 H20A 0.970 no C20 H20B 0.970 no C21 H21A 0.970 no C21 H21B 0.970 no C22 H22A 0.970 no C22 H22B 0.970 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag S1 N1 3.436(4) . no S1 C7 3.698(4) . no S1 C12 3.397(6) . no S1 C20 3.580(5) 1_545 no S1 C7 3.636(5) 2_655 no S1 H7B 3.040 . no S1 H12 3.120 . no S1 H20A 3.190 1_545 no S1 H20B 3.100 1_545 no S1 H18A 3.030 . no S1 H4 3.020 2_665 no S1 H7A 3.120 2_655 no O1 N4 2.873(6) . no O1 C13 3.363(7) 2_666 no O1 H13 2.570 2_666 no O1 H19B 2.890 2_676 no N1 S1 3.436(4) . no N1 N2 2.175(5) . no N1 N3 3.246(5) . no N1 C3 3.439(7) 2_665 no N1 C4 3.262(7) 2_665 no N2 N1 2.175(5) . no N2 N3 3.115(5) . no N2 N4 3.112(6) . no N3 N1 3.246(5) . no N3 N2 3.115(5) . no N3 C17 3.371(6) . no N3 C21 3.367(6) 1_655 no N4 N2 3.112(6) . no N4 O1 2.873(6) . no N3 H21A 2.860 1_655 no N3 H17B 2.780 . no N4 H5 2.880 2_665 no C1 C5 3.338(7) 2_665 no C1 C8 3.508(8) 2_765 no C3 N1 3.439(7) 2_665 no C3 C7 3.438(7) 2_665 no C4 C9 3.483(7) 2_665 no C4 N1 3.262(7) 2_665 no C4 C6 3.405(7) 2_665 no C5 C6 3.340(7) 2_665 no C5 C1 3.338(7) 2_665 no C6 C6 3.550(7) 2_665 no C6 C4 3.405(7) 2_665 no C6 C8 3.581(8) 2_765 no C6 C5 3.340(7) 2_665 no C7 S1 3.698(4) . no C7 S1 3.636(5) 2_655 no C7 C3 3.438(7) 2_665 no C8 C6 3.581(8) 2_765 no C8 C1 3.508(8) 2_765 no C9 C4 3.483(7) 2_665 no C10 C18 3.531(7) . no C11 C21 3.488(6) 1_655 no C12 S1 3.397(6) . no C13 O1 3.363(7) 2_666 no C17 N3 3.371(6) . no C18 C10 3.531(7) . no C20 S1 3.580(5) 1_565 no C21 N3 3.367(6) 1_455 no C21 C11 3.488(6) 1_455 no C2 H17A 2.850 . no C3 H7A 3.010 2_665 no C4 H16 2.810 2_765 no C5 H7A 2.880 . no C7 H5 2.980 . no C9 H18A 3.050 . no C9 H8C 3.080 . no C10 H7B 2.760 . no C10 H12 2.910 . no C10 H18A 2.990 . no C10 H17B 2.800 . no C11 H21B 2.970 1_655 no C12 H21B 3.080 1_655 no C13 H14 3.060 2_756 no C13 H19A 2.960 1_545 no C14 H17A 2.970 1_545 no C14 H18B 3.040 2_766 no C15 H8B 3.030 2_755 no C15 H22B 3.080 1_655 no C16 H2 3.080 1_545 no C16 H22B 2.860 1_655 no C17 H2 3.030 . no C17 H19A 2.770 . no C19 H17A 2.750 . no H2 C16 3.080 1_565 no H2 C17 3.030 . no H2 H17A 2.460 . no H2 H19A 2.370 . no H3 H7B 2.370 1_565 no H4 S1 3.020 2_665 no H4 H16 2.390 2_765 no H5 C7 2.980 . no H5 H7A 2.470 . no H5 N4 2.880 2_665 no H5 H21A 2.580 2_665 no H7A C5 2.880 . no H7A H5 2.470 . no H7A S1 3.120 2_655 no H7A C3 3.010 2_665 no H7A H20B 2.550 2_665 no H7B S1 3.040 . no H7B C10 2.760 . no H7B H3 2.370 1_545 no H8B C15 3.030 2_755 no H8B H15 2.450 2_755 no H8C C9 3.080 . no H12 S1 3.120 . no H12 C10 2.910 . no H13 O1 2.570 2_666 no H13 H14 2.440 2_756 no H14 C13 3.060 2_756 no H14 H13 2.440 2_756 no H15 H8B 2.450 2_755 no H16 C4 2.810 2_765 no H16 H4 2.390 2_765 no H17A C2 2.850 . no H17A C14 2.970 1_565 no H17A C19 2.750 . no H17A H2 2.460 . no H17A H19A 2.190 . no H17B N3 2.780 . no H17B C10 2.800 . no H18A S1 3.030 . no H18A C9 3.050 . no H18A C10 2.990 . no H18A H22B 2.310 . no H18B H19B 2.340 . no H18B H22A 2.430 . no H18B C14 3.040 2_766 no H19A C13 2.960 1_565 no H19A C17 2.770 . no H19A H2 2.370 . no H19A H17A 2.190 . no H19B H18B 2.340 . no H19B H22A 2.430 . no H19B O1 2.890 2_676 no H19B H20A 2.510 2_676 no H20A S1 3.190 1_565 no H20A H19B 2.510 2_676 no H20B S1 3.100 1_565 no H20B H21A 2.370 . no H20B H7A 2.550 2_665 no H21A N3 2.860 1_455 no H21A H20B 2.370 . no H21A H5 2.580 2_665 no H21B C11 2.970 1_455 no H21B C12 3.080 1_455 no H22A H18B 2.430 . no H22A H19B 2.430 . no H22B C15 3.080 1_455 no H22B C16 2.860 1_455 no H22B H18A 2.310 . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C13 H13 O1 2_666 0.93 2.57 3.363(7) 144 yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag C21 O1 C20 C19 -57.2(5) no C20 O1 C21 C22 57.2(5) no C6 N1 C9 N2 1.0(5) no C7 N1 C6 C1 -176.9(4) no C9 N1 C7 C8 -88.9(5) no C7 N1 C9 C10 -3.1(7) no C7 N1 C6 C5 5.8(8) no C9 N1 C6 C5 -178.1(5) no C6 N1 C7 C8 86.5(5) no C9 N1 C6 C1 -0.8(5) no C6 N1 C9 C10 -179.1(4) no C7 N1 C9 N2 176.9(4) no C9 N2 C1 C2 179.5(5) no C17 N2 C9 C10 2.8(7) no C17 N2 C9 N1 -177.2(4) no C1 N2 C9 C10 179.3(4) no C1 N2 C17 C18 102.9(5) no C9 N2 C1 C6 0.2(5) no C9 N2 C17 C18 -81.3(5) no C17 N2 C1 C6 176.6(4) no C1 N2 C9 N1 -0.7(5) no C17 N2 C1 C2 -4.1(8) no C10 N3 C11 C12 -59.8(6) no C11 N3 C10 S1 -5.7(7) no C10 N3 C11 C16 126.8(5) no C11 N3 C10 C9 175.4(4) no C22 N4 C19 C20 -57.3(5) no C19 N4 C22 C21 56.9(5) no C22 N4 C18 C17 170.3(4) no C18 N4 C22 C21 178.2(4) no C18 N4 C19 C20 -177.3(4) no C19 N4 C18 C17 -70.4(5) no N2 C1 C6 C5 178.0(4) no C2 C1 C6 C5 -1.5(7) no C2 C1 C6 N1 -179.1(4) no N2 C1 C6 N1 0.4(5) no C6 C1 C2 C3 0.4(7) no N2 C1 C2 C3 -178.9(5) no C1 C2 C3 C4 1.3(8) no C2 C3 C4 C5 -1.9(9) no C3 C4 C5 C6 0.7(8) no C4 C5 C6 C1 0.9(7) no C4 C5 C6 N1 177.8(5) no N1 C9 C10 N3 100.3(5) no N2 C9 C10 S1 101.1(4) no N2 C9 C10 N3 -79.8(5) no N1 C9 C10 S1 -78.9(5) no N3 C11 C16 C15 173.3(4) no C12 C11 C16 C15 -0.3(7) no N3 C11 C12 C13 -173.5(4) no C16 C11 C12 C13 -0.3(7) no C11 C12 C13 C14 0.6(7) no C12 C13 C14 C15 -0.3(8) no C13 C14 C15 C16 -0.3(8) no C14 C15 C16 C11 0.6(7) no N2 C17 C18 N4 -67.5(5) no N4 C19 C20 O1 59.0(5) no O1 C21 C22 N4 -58.6(6) no