# Electronic Supplementary Material (ESI) for RSC Advances. # This journal is © The Royal Society of Chemistry 2020 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_shelx _database_code_depnum_ccdc_archive 'CCDC 2022218' loop_ _audit_author_name _audit_author_address 'O. Blacque' ;University of Zurich Switzerland ; _audit_update_record ; 2020-08-08 deposited with the CCDC. 2020-09-28 downloaded from the CCDC. ; _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H9 N3 O S2' _chemical_formula_weight 263.33 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/n' _space_group_name_Hall '-P 2yn' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.5546(2) _cell_length_b 4.9907(5) _cell_length_c 17.1813(3) _cell_angle_alpha 90 _cell_angle_beta 113.268(2) _cell_angle_gamma 90 _cell_volume 1146.50(12) _cell_formula_units_Z 4 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 7920 _cell_measurement_theta_max 79.0 _cell_measurement_theta_min 3.4 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.526 _exptl_crystal_F_000 544 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.090 _exptl_crystal_size_mid 0.090 _exptl_crystal_size_min 0.030 _exptl_absorpt_coefficient_mu 4.102 _shelx_estimated_absorpt_T_min 0.709 _shelx_estimated_absorpt_T_max 0.887 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.745 _exptl_absorpt_correction_T_max 0.908 _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_special_details ? _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, Pilatus 200K' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 5.8140 _diffrn_reflns_number 11447 _diffrn_reflns_av_unetI/netI 0.0209 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.384 _diffrn_reflns_theta_max 74.466 _diffrn_reflns_theta_full 67.684 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_point_group_measured_fraction_full 0.999 _reflns_number_total 2336 _reflns_number_gt 2147 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_cell_refinement 'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015b)' _computing_structure_solution 'ShelXT (Sheldrick, 2015a)' _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0358P)^2^+0.4259P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 2336 _refine_ls_number_parameters 159 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0270 _refine_ls_R_factor_gt 0.0249 _refine_ls_wR_factor_ref 0.0687 _refine_ls_wR_factor_gt 0.0674 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.42521(2) 0.59528(7) 0.34017(2) 0.02616(11) Uani 1 1 d . . . . . S2 S 0.76320(2) 0.74865(6) 0.32497(2) 0.02129(10) Uani 1 1 d . . . . . O6 O 0.62778(7) -0.0907(2) 0.53533(6) 0.0268(2) Uani 1 1 d . . . . . N3 N 0.61745(8) 0.5081(2) 0.37174(7) 0.0201(2) Uani 1 1 d . . . . . N2 N 0.87904(10) -0.0633(3) 0.56368(8) 0.0339(3) Uani 1 1 d . . . . . N1 N 0.54303(9) 0.2397(2) 0.44340(8) 0.0226(2) Uani 1 1 d . . . . . H1 H 0.4878(16) 0.195(4) 0.4500(13) 0.043(5) Uiso 1 1 d . . . . . C2 C 0.54074(10) 0.4376(3) 0.38833(8) 0.0206(3) Uani 1 1 d . . . . . C6 C 0.62894(10) 0.0950(3) 0.48798(8) 0.0215(3) Uani 1 1 d . . . . . C5 C 0.71540(9) 0.1793(3) 0.47324(8) 0.0203(3) Uani 1 1 d . . . . . C4 C 0.70668(9) 0.3793(3) 0.41452(8) 0.0184(3) Uani 1 1 d . . . . . C7 C 0.44546(10) 0.8079(3) 0.26273(9) 0.0258(3) Uani 1 1 d . . . . . H71 H 0.498770 0.940227 0.291544 0.031 Uiso 1 1 calc R U . . . H72 H 0.466061 0.698405 0.224329 0.031 Uiso 1 1 calc R U . . . C8 C 0.34727(12) 0.9505(3) 0.21272(10) 0.0352(4) Uani 1 1 d . . . . . H81 H 0.324724 1.045665 0.251883 0.053 Uiso 1 1 calc R U . . . H82 H 0.296669 0.818608 0.180453 0.053 Uiso 1 1 calc R U . . . H83 H 0.357198 1.079059 0.173626 0.053 Uiso 1 1 calc R U . . . C9 C 0.80637(10) 0.0445(3) 0.52234(9) 0.0233(3) Uani 1 1 d . . . . . C10 C 0.78716(9) 0.4741(3) 0.39190(8) 0.0187(3) Uani 1 1 d . . . . . C11 C 0.88466(10) 0.3844(3) 0.41504(8) 0.0210(3) Uani 1 1 d . . . . . H11 H 0.912243 0.235258 0.451109 0.025 Uiso 1 1 calc R U . . . C12 C 0.93798(10) 0.5417(3) 0.37841(9) 0.0236(3) Uani 1 1 d . . . . . H12 H 1.005713 0.509391 0.387277 0.028 Uiso 1 1 calc R U . . . C13 C 0.88233(10) 0.7440(3) 0.32922(9) 0.0241(3) Uani 1 1 d . . . . . H13 H 0.907012 0.868893 0.300427 0.029 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.01784(16) 0.0332(2) 0.02934(18) 0.00697(14) 0.01142(13) 0.00372(13) S2 0.01976(17) 0.02136(18) 0.02431(17) 0.00314(12) 0.01038(13) 0.00033(11) O6 0.0252(5) 0.0285(5) 0.0307(5) 0.0088(4) 0.0153(4) 0.0014(4) N3 0.0177(5) 0.0225(5) 0.0210(5) 0.0007(4) 0.0088(4) 0.0001(4) N2 0.0272(6) 0.0395(7) 0.0346(7) 0.0128(6) 0.0117(5) 0.0049(6) N1 0.0187(5) 0.0267(6) 0.0257(6) 0.0038(5) 0.0125(5) -0.0005(4) C2 0.0198(6) 0.0227(6) 0.0201(6) -0.0013(5) 0.0089(5) -0.0006(5) C6 0.0224(6) 0.0227(6) 0.0212(6) 0.0006(5) 0.0107(5) -0.0002(5) C5 0.0195(6) 0.0221(6) 0.0205(6) -0.0005(5) 0.0093(5) -0.0001(5) C4 0.0182(6) 0.0195(6) 0.0180(6) -0.0030(5) 0.0077(5) -0.0009(5) C7 0.0243(6) 0.0298(7) 0.0246(7) 0.0044(6) 0.0110(5) 0.0031(6) C8 0.0317(8) 0.0392(9) 0.0344(8) 0.0086(7) 0.0126(6) 0.0119(7) C9 0.0243(7) 0.0245(7) 0.0236(6) 0.0033(5) 0.0121(5) -0.0009(6) C10 0.0198(6) 0.0190(6) 0.0177(6) -0.0007(5) 0.0080(5) -0.0015(5) C11 0.0195(6) 0.0230(6) 0.0212(6) -0.0004(5) 0.0087(5) -0.0010(5) C12 0.0169(6) 0.0288(7) 0.0257(6) -0.0015(6) 0.0090(5) -0.0019(5) C13 0.0219(6) 0.0270(7) 0.0269(7) -0.0009(5) 0.0133(5) -0.0054(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C2 1.7412(13) . ? S1 C7 1.8143(14) . ? S2 C13 1.7065(14) . ? S2 C10 1.7331(13) . ? O6 C6 1.2376(17) . ? N3 C2 1.3049(17) . ? N3 C4 1.3733(17) . ? N2 C9 1.1484(19) . ? N1 C2 1.3590(18) . ? N1 C6 1.3839(18) . ? N1 H1 0.88(2) . ? C6 C5 1.4411(18) . ? C5 C4 1.3887(19) . ? C5 C9 1.4266(19) . ? C4 C10 1.4515(17) . ? C7 C8 1.522(2) . ? C7 H71 0.9900 . ? C7 H72 0.9900 . ? C8 H81 0.9800 . ? C8 H82 0.9800 . ? C8 H83 0.9800 . ? C10 C11 1.3882(18) . ? C11 C12 1.4144(19) . ? C11 H11 0.9500 . ? C12 C13 1.360(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? 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 S1 C7 101.93(6) . . ? C13 S2 C10 91.50(6) . . ? C2 N3 C4 117.83(11) . . ? C2 N1 C6 122.20(12) . . ? C2 N1 H1 120.0(14) . . ? C6 N1 H1 117.7(14) . . ? N3 C2 N1 124.07(12) . . ? N3 C2 S1 121.56(10) . . ? N1 C2 S1 114.37(10) . . ? O6 C6 N1 120.71(12) . . ? O6 C6 C5 125.02(12) . . ? N1 C6 C5 114.27(11) . . ? C4 C5 C9 124.46(12) . . ? C4 C5 C6 120.13(12) . . ? C9 C5 C6 115.41(12) . . ? N3 C4 C5 121.39(12) . . ? N3 C4 C10 113.36(11) . . ? C5 C4 C10 125.25(12) . . ? C8 C7 S1 107.41(10) . . ? C8 C7 H71 110.2 . . ? S1 C7 H71 110.2 . . ? C8 C7 H72 110.2 . . ? S1 C7 H72 110.2 . . ? H71 C7 H72 108.5 . . ? C7 C8 H81 109.5 . . ? C7 C8 H82 109.5 . . ? H81 C8 H82 109.5 . . ? C7 C8 H83 109.5 . . ? H81 C8 H83 109.5 . . ? H82 C8 H83 109.5 . . ? N2 C9 C5 178.24(15) . . ? C11 C10 C4 131.28(12) . . ? C11 C10 S2 111.11(10) . . ? C4 C10 S2 117.61(9) . . ? C10 C11 C12 111.83(12) . . ? C10 C11 H11 124.1 . . ? C12 C11 H11 124.1 . . ? C13 C12 C11 113.08(12) . . ? C13 C12 H12 123.5 . . ? C11 C12 H12 123.5 . . ? C12 C13 S2 112.48(10) . . ? C12 C13 H13 123.8 . . ? S2 C13 H13 123.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N3 C2 N1 -1.99(19) . . . . ? C4 N3 C2 S1 177.95(9) . . . . ? C6 N1 C2 N3 0.6(2) . . . . ? C6 N1 C2 S1 -179.34(10) . . . . ? C7 S1 C2 N3 7.47(13) . . . . ? C7 S1 C2 N1 -172.58(10) . . . . ? C2 N1 C6 O6 -177.32(13) . . . . ? C2 N1 C6 C5 2.23(19) . . . . ? O6 C6 C5 C4 175.84(13) . . . . ? N1 C6 C5 C4 -3.68(18) . . . . ? O6 C6 C5 C9 -4.2(2) . . . . ? N1 C6 C5 C9 176.31(12) . . . . ? C2 N3 C4 C5 0.36(18) . . . . ? C2 N3 C4 C10 -179.52(11) . . . . ? C9 C5 C4 N3 -177.45(12) . . . . ? C6 C5 C4 N3 2.55(19) . . . . ? C9 C5 C4 C10 2.4(2) . . . . ? C6 C5 C4 C10 -177.59(12) . . . . ? C2 S1 C7 C8 177.57(11) . . . . ? N3 C4 C10 C11 -174.27(13) . . . . ? C5 C4 C10 C11 5.9(2) . . . . ? N3 C4 C10 S2 6.23(15) . . . . ? C5 C4 C10 S2 -173.64(10) . . . . ? C13 S2 C10 C11 -0.62(10) . . . . ? C13 S2 C10 C4 178.97(10) . . . . ? C4 C10 C11 C12 -179.08(13) . . . . ? S2 C10 C11 C12 0.45(14) . . . . ? C10 C11 C12 C13 0.04(17) . . . . ? C11 C12 C13 S2 -0.52(16) . . . . ? C10 S2 C13 C12 0.65(11) . . . . ? _refine_diff_density_max 0.287 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.045 _shelx_res_file ; TITL emam15_a.res in P2(1)/n shelx.res created by SHELXL-2018/3 at 23:15:33 on 17-Mar-2020 CELL 1.54184 14.5546 4.9907 17.1813 90.000 113.268 90.000 ZERR 4.00 0.0002 0.0005 0.0003 0.000 0.002 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O S UNIT 44 36 12 4 8 MERG 2 MORE -1 FMAP 2 PLAN 20 SIZE 0.030 0.090 0.090 ACTA BOND $H OMIT 1 2 4 OMIT 0 -6 4 OMIT 0 2 0 OMIT 1 1 2 OMIT 0 -5 5 OMIT 1 -3 2 CONF L.S. 8 TEMP -113 WGHT 0.035800 0.425900 FVAR 3.67741 S1 5 0.425215 0.595283 0.340167 11.00000 0.01784 0.03325 = 0.02934 0.00697 0.01142 0.00372 S2 5 0.763200 0.748647 0.324971 11.00000 0.01976 0.02136 = 0.02431 0.00314 0.01038 0.00033 O6 4 0.627782 -0.090679 0.535329 11.00000 0.02523 0.02847 = 0.03070 0.00880 0.01529 0.00141 N3 3 0.617451 0.508080 0.371742 11.00000 0.01774 0.02250 = 0.02104 0.00068 0.00884 0.00009 N2 3 0.879041 -0.063295 0.563679 11.00000 0.02724 0.03946 = 0.03457 0.01281 0.01172 0.00489 N1 3 0.543028 0.239727 0.443396 11.00000 0.01873 0.02666 = 0.02574 0.00377 0.01247 -0.00053 H1 2 0.487785 0.194858 0.450002 11.00000 0.04251 C2 1 0.540745 0.437632 0.388329 11.00000 0.01981 0.02268 = 0.02014 -0.00133 0.00888 -0.00062 C6 1 0.628939 0.094992 0.487979 11.00000 0.02241 0.02274 = 0.02125 0.00060 0.01065 -0.00021 C5 1 0.715403 0.179340 0.473243 11.00000 0.01954 0.02206 = 0.02050 -0.00049 0.00932 -0.00009 C4 1 0.706681 0.379268 0.414522 11.00000 0.01825 0.01947 = 0.01803 -0.00298 0.00767 -0.00093 C7 1 0.445455 0.807857 0.262735 11.00000 0.02426 0.02976 = 0.02458 0.00442 0.01101 0.00309 AFIX 23 H71 2 0.498770 0.940227 0.291544 11.00000 -1.20000 H72 2 0.466061 0.698405 0.224329 11.00000 -1.20000 AFIX 0 C8 1 0.347268 0.950500 0.212720 11.00000 0.03170 0.03920 = 0.03441 0.00865 0.01261 0.01193 AFIX 137 H81 2 0.324724 1.045665 0.251883 11.00000 -1.50000 H82 2 0.296669 0.818608 0.180453 11.00000 -1.50000 H83 2 0.357198 1.079059 0.173626 11.00000 -1.50000 AFIX 0 C9 1 0.806367 0.044464 0.522343 11.00000 0.02431 0.02454 = 0.02363 0.00325 0.01214 -0.00092 C10 1 0.787155 0.474150 0.391899 11.00000 0.01977 0.01898 = 0.01774 -0.00068 0.00799 -0.00149 C11 1 0.884660 0.384369 0.415037 11.00000 0.01949 0.02299 = 0.02124 -0.00037 0.00869 -0.00097 AFIX 43 H11 2 0.912243 0.235258 0.451109 11.00000 -1.20000 AFIX 0 C12 1 0.937980 0.541724 0.378415 11.00000 0.01690 0.02882 = 0.02568 -0.00152 0.00896 -0.00194 AFIX 43 H12 2 1.005713 0.509391 0.387277 11.00000 -1.20000 AFIX 0 C13 1 0.882327 0.744038 0.329220 11.00000 0.02186 0.02705 = 0.02688 -0.00091 0.01327 -0.00535 AFIX 43 H13 2 0.907012 0.868893 0.300427 11.00000 -1.20000 AFIX 0 HKLF 4 REM emam15_a.res in P2(1)/n REM wR2 = 0.0687, GooF = S = 1.064, Restrained GooF = 1.064 for all data REM R1 = 0.0249 for 2144 Fo > 4sig(Fo) and 0.0270 for all 2333 data REM 159 parameters refined using 0 restraints END WGHT 0.0358 0.4260 REM Highest difference peak 0.287, deepest hole -0.224, 1-sigma level 0.045 Q1 1 0.9168 0.4761 0.4062 11.00000 0.05 0.29 Q2 1 0.6782 0.1412 0.4779 11.00000 0.05 0.29 Q3 1 0.7525 0.4401 0.4103 11.00000 0.05 0.25 Q4 1 0.8393 0.7537 0.3296 11.00000 0.05 0.24 Q5 1 0.7152 0.2896 0.4531 11.00000 0.05 0.24 Q6 1 0.8358 0.4236 0.4052 11.00000 0.05 0.23 Q7 1 0.7784 0.5839 0.3695 11.00000 0.05 0.22 Q8 1 0.7575 0.1359 0.4986 11.00000 0.05 0.22 Q9 1 0.4020 0.4548 0.3038 11.00000 0.05 0.20 Q10 1 0.5412 0.3571 0.4160 11.00000 0.05 0.20 Q11 1 0.5814 0.1951 0.4651 11.00000 0.05 0.19 Q12 1 0.4412 0.7294 0.2953 11.00000 0.05 0.19 Q13 1 0.3979 0.8891 0.2401 11.00000 0.05 0.18 Q14 1 0.5848 0.4874 0.3872 11.00000 0.05 0.18 Q15 1 0.4865 0.4969 0.3680 11.00000 0.05 0.18 Q16 1 0.6605 0.4352 0.3962 11.00000 0.05 0.17 Q17 1 0.8990 0.6080 0.3363 11.00000 0.05 0.17 Q18 1 0.9185 0.6918 0.3797 11.00000 0.05 0.16 Q19 1 0.6153 0.6347 0.3455 11.00000 0.05 0.15 Q20 1 0.5824 0.7241 0.3201 11.00000 0.05 0.14 ; _shelx_res_checksum 83688 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_shelx_CCDC1 _database_code_depnum_ccdc_archive 'CCDC 2022219' loop_ _audit_author_name _audit_author_address 'O. Blacque' ;University of Zurich Switzerland ; _audit_update_record ; 2020-08-08 deposited with the CCDC. 2020-09-28 downloaded from the CCDC. ; _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H11 N3 O S' _chemical_formula_weight 257.31 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.6908(2) _cell_length_b 9.2376(3) _cell_length_c 14.6613(3) _cell_angle_alpha 94.308(2) _cell_angle_beta 93.766(2) _cell_angle_gamma 100.924(3) _cell_volume 619.95(4) _cell_formula_units_Z 2 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 7574 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 77.7 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.378 _exptl_crystal_F_000 268 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.130 _exptl_crystal_size_mid 0.030 _exptl_crystal_size_min 0.020 _exptl_absorpt_coefficient_mu 2.248 _shelx_estimated_absorpt_T_min 0.759 _shelx_estimated_absorpt_T_max 0.956 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.848 _exptl_absorpt_correction_T_max 0.960 _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_special_details ? _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, Pilatus 200K' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 5.8140 _diffrn_reflns_number 13068 _diffrn_reflns_av_unetI/netI 0.0246 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.033 _diffrn_reflns_theta_max 74.464 _diffrn_reflns_theta_full 67.684 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_point_group_measured_fraction_full 1.000 _reflns_number_total 2524 _reflns_number_gt 2219 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_cell_refinement 'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015b)' _computing_structure_solution 'ShelXT (Sheldrick, 2015a)' _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0485P)^2^+0.1743P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 2524 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0383 _refine_ls_R_factor_gt 0.0327 _refine_ls_wR_factor_ref 0.0888 _refine_ls_wR_factor_gt 0.0859 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S -0.07309(8) 0.14886(4) 0.90110(2) 0.03368(13) Uani 1 1 d . . . . . O6 O 0.7377(2) 0.56822(12) 0.92095(7) 0.0377(3) Uani 1 1 d . . . . . N3 N 0.2302(3) 0.22848(13) 0.75839(8) 0.0275(3) Uani 1 1 d . . . . . N2 N 1.0506(4) 0.6220(2) 0.72002(10) 0.0665(6) Uani 1 1 d . . . . . N1 N 0.3520(3) 0.37484(13) 0.89931(8) 0.0299(3) Uani 1 1 d . . . . . H1 H 0.316(4) 0.392(2) 0.9587(16) 0.057(6) Uiso 1 1 d . . . . . C2 C 0.1928(3) 0.25870(15) 0.84511(10) 0.0278(3) Uani 1 1 d . . . . . C6 C 0.5843(3) 0.46832(15) 0.86887(9) 0.0292(3) Uani 1 1 d . . . . . C5 C 0.6264(3) 0.43784(15) 0.77324(9) 0.0277(3) Uani 1 1 d . . . . . C4 C 0.4474(3) 0.32038(15) 0.72078(9) 0.0254(3) Uani 1 1 d . . . . . C7 C -0.2329(3) 0.00253(17) 0.81269(11) 0.0360(3) Uani 1 1 d . . . . . H71 H -0.330130 0.043534 0.761410 0.043 Uiso 1 1 calc R U . . . H72 H -0.080550 -0.046990 0.788338 0.043 Uiso 1 1 calc R U . . . C8 C -0.4520(4) -0.1060(2) 0.85724(13) 0.0495(4) Uani 1 1 d . . . . . H81 H -0.552643 -0.184146 0.810913 0.074 Uiso 1 1 calc R U . . . H82 H -0.594290 -0.054168 0.884340 0.074 Uiso 1 1 calc R U . . . H83 H -0.351000 -0.150108 0.905368 0.074 Uiso 1 1 calc R U . . . C9 C 0.8597(4) 0.53841(18) 0.74085(10) 0.0377(4) Uani 1 1 d . . . . . C10 C 0.4687(3) 0.28429(15) 0.62158(9) 0.0257(3) Uani 1 1 d . . . . . C11A C 0.7349(6) 0.3195(3) 0.58165(19) 0.0288(7) Uani 0.501(3) 1 d . . P A 1 H111 H 0.907480 0.362822 0.619089 0.035 Uiso 0.501(3) 1 calc R U P A 1 C11B C 0.5757(6) 0.3944(3) 0.56483(19) 0.0300(7) Uani 0.499(3) 1 d . . P A 2 H112 H 0.638403 0.494030 0.590053 0.036 Uiso 0.499(3) 1 calc R U P A 2 C12A C 0.7465(6) 0.2912(3) 0.48760(19) 0.0299(7) Uani 0.501(3) 1 d . . P A 1 H121 H 0.924366 0.319802 0.460270 0.036 Uiso 0.501(3) 1 calc R U P A 1 C12B C 0.5900(7) 0.3581(3) 0.4721(2) 0.0330(7) Uani 0.499(3) 1 d . . P A 2 H122 H 0.669271 0.433239 0.434938 0.040 Uiso 0.499(3) 1 calc R U P A 2 C13 C 0.4954(3) 0.22053(17) 0.43356(10) 0.0318(3) Uani 1 1 d . . . . . H131 H 0.505377 0.195620 0.369949 0.038 Uiso 0.501(3) 1 calc R U P A 1 H132 H 0.501799 0.198819 0.369442 0.038 Uiso 0.499(3) 1 calc R U P A 2 C14A C 0.2349(7) 0.1869(3) 0.4717(2) 0.0328(7) Uani 0.501(3) 1 d . . P A 1 H141 H 0.062719 0.144981 0.433782 0.039 Uiso 0.501(3) 1 calc R U P A 1 C14B C 0.3835(6) 0.1050(3) 0.49002(19) 0.0300(7) Uani 0.499(3) 1 d . . P A 2 H142 H 0.321559 0.005754 0.463919 0.036 Uiso 0.499(3) 1 calc R U P A 2 C15A C 0.2212(6) 0.2139(3) 0.56574(19) 0.0301(7) Uani 0.501(3) 1 d . . P A 1 H151 H 0.042145 0.184157 0.592197 0.036 Uiso 0.501(3) 1 calc R U P A 1 C15B C 0.3672(6) 0.1403(3) 0.58279(19) 0.0277(7) Uani 0.499(3) 1 d . . P A 2 H152 H 0.286210 0.065741 0.620075 0.033 Uiso 0.499(3) 1 calc R U P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0385(2) 0.0320(2) 0.02679(19) 0.00248(13) 0.00864(14) -0.00458(15) O6 0.0430(6) 0.0365(6) 0.0266(5) -0.0037(4) 0.0072(4) -0.0089(5) N3 0.0295(6) 0.0274(6) 0.0246(6) 0.0018(5) 0.0050(5) 0.0026(5) N2 0.0718(11) 0.0752(12) 0.0315(8) -0.0065(7) 0.0141(7) -0.0374(10) N1 0.0339(6) 0.0300(6) 0.0234(6) -0.0004(5) 0.0076(5) -0.0007(5) C2 0.0304(7) 0.0266(7) 0.0258(7) 0.0025(5) 0.0041(5) 0.0038(5) C6 0.0326(7) 0.0277(7) 0.0260(7) 0.0018(5) 0.0058(6) 0.0015(6) C5 0.0290(7) 0.0288(7) 0.0246(7) 0.0030(5) 0.0053(5) 0.0030(5) C4 0.0258(7) 0.0264(6) 0.0248(7) 0.0034(5) 0.0039(5) 0.0062(5) C7 0.0390(8) 0.0320(8) 0.0330(8) 0.0005(6) 0.0000(6) -0.0010(6) C8 0.0503(10) 0.0405(9) 0.0488(10) 0.0062(8) -0.0016(8) -0.0119(8) C9 0.0400(9) 0.0422(9) 0.0246(7) -0.0026(6) 0.0054(6) -0.0066(7) C10 0.0277(7) 0.0266(7) 0.0238(7) 0.0029(5) 0.0037(5) 0.0072(5) C11A 0.0290(14) 0.0296(14) 0.0279(14) 0.0022(11) 0.0020(11) 0.0060(11) C11B 0.0354(16) 0.0280(14) 0.0267(14) 0.0044(11) 0.0026(11) 0.0053(12) C12A 0.0315(15) 0.0314(15) 0.0288(14) 0.0051(11) 0.0095(11) 0.0073(12) C12B 0.0348(16) 0.0361(16) 0.0281(15) 0.0085(12) 0.0054(12) 0.0040(13) C13 0.0373(8) 0.0372(8) 0.0222(6) 0.0018(6) 0.0040(6) 0.0107(6) C14A 0.0348(15) 0.0345(16) 0.0284(14) 0.0001(12) 0.0020(12) 0.0061(13) C14B 0.0340(15) 0.0270(14) 0.0283(14) -0.0013(11) 0.0032(11) 0.0055(12) C15A 0.0294(14) 0.0322(15) 0.0283(14) 0.0021(11) 0.0065(11) 0.0040(12) C15B 0.0300(14) 0.0290(14) 0.0253(13) 0.0046(11) 0.0051(11) 0.0065(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C2 1.7432(14) . ? S1 C7 1.8150(15) . ? O6 C6 1.2339(17) . ? N3 C2 1.3113(18) . ? N3 C4 1.3707(18) . ? N2 C9 1.141(2) . ? N1 C2 1.3531(18) . ? N1 C6 1.3775(18) . ? N1 H1 0.91(2) . ? C6 C5 1.4429(19) . ? C5 C4 1.385(2) . ? C5 C9 1.427(2) . ? C4 C10 1.4817(19) . ? C7 C8 1.511(2) . ? C7 H71 0.9900 . ? C7 H72 0.9900 . ? C8 H81 0.9800 . ? C8 H82 0.9800 . ? C8 H83 0.9800 . ? C10 C15B 1.389(3) . ? C10 C15A 1.397(3) . ? C10 C11B 1.402(3) . ? C10 C11A 1.407(3) . ? C11A C12A 1.391(4) . ? C11A H111 0.9500 . ? C11B C12B 1.385(4) . ? C11B H112 0.9500 . ? C12A C13 1.396(3) . ? C12A H121 0.9500 . ? C12B C13 1.333(3) . ? C12B H122 0.9500 . ? C13 C14A 1.369(3) . ? C13 C14B 1.442(3) . ? C13 H131 0.9500 . ? C13 H132 0.9500 . ? C14A C15A 1.390(4) . ? C14A H141 0.9500 . ? C14B C15B 1.385(4) . ? C14B H142 0.9500 . ? C15A H151 0.9500 . ? C15B H152 0.9500 . ? 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 S1 C7 102.73(7) . . ? C2 N3 C4 117.49(12) . . ? C2 N1 C6 122.14(12) . . ? C2 N1 H1 121.4(14) . . ? C6 N1 H1 116.4(14) . . ? N3 C2 N1 124.39(13) . . ? N3 C2 S1 121.82(11) . . ? N1 C2 S1 113.79(10) . . ? O6 C6 N1 121.16(12) . . ? O6 C6 C5 124.75(13) . . ? N1 C6 C5 114.09(12) . . ? C4 C5 C9 125.41(13) . . ? C4 C5 C6 120.55(12) . . ? C9 C5 C6 114.04(12) . . ? N3 C4 C5 121.17(12) . . ? N3 C4 C10 114.71(12) . . ? C5 C4 C10 124.11(12) . . ? C8 C7 S1 106.66(11) . . ? C8 C7 H71 110.4 . . ? S1 C7 H71 110.4 . . ? C8 C7 H72 110.4 . . ? S1 C7 H72 110.4 . . ? H71 C7 H72 108.6 . . ? C7 C8 H81 109.5 . . ? C7 C8 H82 109.5 . . ? H81 C8 H82 109.5 . . ? C7 C8 H83 109.5 . . ? H81 C8 H83 109.5 . . ? H82 C8 H83 109.5 . . ? N2 C9 C5 176.09(16) . . ? C15B C10 C11B 119.08(19) . . ? C15A C10 C11A 118.68(19) . . ? C15B C10 C4 119.60(15) . . ? C15A C10 C4 119.96(16) . . ? C11B C10 C4 121.23(16) . . ? C11A C10 C4 121.36(16) . . ? C12A C11A C10 120.3(2) . . ? C12A C11A H111 119.9 . . ? C10 C11A H111 119.9 . . ? C12B C11B C10 120.1(2) . . ? C12B C11B H112 119.9 . . ? C10 C11B H112 119.9 . . ? C11A C12A C13 119.6(2) . . ? C11A C12A H121 120.2 . . ? C13 C12A H121 120.2 . . ? C13 C12B C11B 121.8(3) . . ? C13 C12B H122 119.1 . . ? C11B C12B H122 119.1 . . ? C14A C13 C12A 120.4(2) . . ? C12B C13 C14B 119.43(19) . . ? C14A C13 H131 119.8 . . ? C12A C13 H131 119.8 . . ? C12B C13 H132 120.3 . . ? C14B C13 H132 120.3 . . ? C13 C14A C15A 120.3(3) . . ? C13 C14A H141 119.8 . . ? C15A C14A H141 119.8 . . ? C15B C14B C13 119.2(2) . . ? C15B C14B H142 120.4 . . ? C13 C14B H142 120.4 . . ? C14A C15A C10 120.5(2) . . ? C14A C15A H151 119.8 . . ? C10 C15A H151 119.8 . . ? C14B C15B C10 120.3(2) . . ? C14B C15B H152 119.8 . . ? C10 C15B H152 119.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N3 C2 N1 0.6(2) . . . . ? C4 N3 C2 S1 -179.20(10) . . . . ? C6 N1 C2 N3 -4.1(2) . . . . ? C6 N1 C2 S1 175.68(11) . . . . ? C7 S1 C2 N3 2.07(14) . . . . ? C7 S1 C2 N1 -177.77(11) . . . . ? C2 N1 C6 O6 -175.59(14) . . . . ? C2 N1 C6 C5 4.5(2) . . . . ? O6 C6 C5 C4 178.21(14) . . . . ? N1 C6 C5 C4 -1.9(2) . . . . ? O6 C6 C5 C9 -2.3(2) . . . . ? N1 C6 C5 C9 177.60(13) . . . . ? C2 N3 C4 C5 2.1(2) . . . . ? C2 N3 C4 C10 -177.19(12) . . . . ? C9 C5 C4 N3 179.26(14) . . . . ? C6 C5 C4 N3 -1.3(2) . . . . ? C9 C5 C4 C10 -1.6(2) . . . . ? C6 C5 C4 C10 177.83(13) . . . . ? C2 S1 C7 C8 175.62(12) . . . . ? N3 C4 C10 C15B -25.4(2) . . . . ? C5 C4 C10 C15B 155.37(18) . . . . ? N3 C4 C10 C15A 27.8(2) . . . . ? C5 C4 C10 C15A -151.43(19) . . . . ? N3 C4 C10 C11B 151.21(18) . . . . ? C5 C4 C10 C11B -28.0(2) . . . . ? N3 C4 C10 C11A -152.21(18) . . . . ? C5 C4 C10 C11A 28.6(2) . . . . ? C15A C10 C11A C12A 3.2(3) . . . . ? C4 C10 C11A C12A -176.8(2) . . . . ? C15B C10 C11B C12B -2.5(4) . . . . ? C4 C10 C11B C12B -179.2(2) . . . . ? C10 C11A C12A C13 -3.3(4) . . . . ? C10 C11B C12B C13 2.2(4) . . . . ? C11B C12B C13 C14B -2.0(4) . . . . ? C11A C12A C13 C14A 3.8(4) . . . . ? C12A C13 C14A C15A -4.3(4) . . . . ? C12B C13 C14B C15B 2.2(4) . . . . ? C13 C14A C15A C10 4.2(4) . . . . ? C11A C10 C15A C14A -3.6(4) . . . . ? C4 C10 C15A C14A 176.4(2) . . . . ? C13 C14B C15B C10 -2.6(4) . . . . ? C11B C10 C15B C14B 2.8(4) . . . . ? C4 C10 C15B C14B 179.5(2) . . . . ? _refine_diff_density_max 0.303 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.041 _shelx_res_file ; TITL emam16_a.res in P-1 shelx.res created by SHELXL-2018/3 at 07:16:11 on 08-Aug-2020 CELL 1.54184 4.6908 9.2376 14.6613 94.308 93.766 100.924 ZERR 2.00 0.0002 0.0003 0.0003 0.002 0.002 0.003 LATT 1 SFAC C H N O S UNIT 26 22 6 2 2 MERG 2 MORE -1 FMAP 2 PLAN 20 SIZE 0.020 0.030 0.130 ACTA BOND $H CONF L.S. 8 TEMP -113 WGHT 0.048500 0.174300 FVAR 2.83313 0.50124 S1 5 -0.073093 0.148855 0.901102 11.00000 0.03845 0.03204 = 0.02679 0.00248 0.00864 -0.00458 O6 4 0.737697 0.568216 0.920950 11.00000 0.04299 0.03649 = 0.02656 -0.00367 0.00720 -0.00888 N3 3 0.230227 0.228481 0.758394 11.00000 0.02950 0.02739 = 0.02462 0.00175 0.00496 0.00258 N2 3 1.050645 0.622039 0.720017 11.00000 0.07180 0.07522 = 0.03147 -0.00645 0.01412 -0.03742 N1 3 0.352030 0.374836 0.899306 11.00000 0.03393 0.03005 = 0.02338 -0.00037 0.00760 -0.00074 H1 2 0.316308 0.392460 0.958656 11.00000 0.05723 C2 1 0.192762 0.258697 0.845106 11.00000 0.03042 0.02655 = 0.02585 0.00252 0.00406 0.00377 C6 1 0.584332 0.468318 0.868867 11.00000 0.03256 0.02766 = 0.02599 0.00176 0.00578 0.00147 C5 1 0.626434 0.437837 0.773243 11.00000 0.02904 0.02885 = 0.02463 0.00298 0.00528 0.00303 C4 1 0.447376 0.320381 0.720781 11.00000 0.02576 0.02636 = 0.02477 0.00341 0.00390 0.00616 C7 1 -0.232872 0.002529 0.812690 11.00000 0.03905 0.03199 = 0.03297 0.00055 0.00000 -0.00096 AFIX 23 H71 2 -0.330130 0.043534 0.761410 11.00000 -1.20000 H72 2 -0.080550 -0.046990 0.788338 11.00000 -1.20000 AFIX 0 C8 1 -0.451958 -0.106013 0.857244 11.00000 0.05034 0.04054 = 0.04882 0.00625 -0.00160 -0.01195 AFIX 137 H81 2 -0.552643 -0.184146 0.810913 11.00000 -1.50000 H82 2 -0.594290 -0.054168 0.884340 11.00000 -1.50000 H83 2 -0.351000 -0.150108 0.905368 11.00000 -1.50000 AFIX 0 C9 1 0.859748 0.538407 0.740852 11.00000 0.04005 0.04218 = 0.02458 -0.00259 0.00538 -0.00658 C10 1 0.468707 0.284293 0.621583 11.00000 0.02770 0.02663 = 0.02379 0.00290 0.00373 0.00723 PART 1 C11A 1 0.734910 0.319514 0.581651 21.00000 0.02898 0.02962 = 0.02785 0.00221 0.00197 0.00605 AFIX 43 H111 2 0.907480 0.362822 0.619089 21.00000 -1.20000 AFIX 0 PART 2 C11B 1 0.575661 0.394386 0.564832 -21.00000 0.03538 0.02797 = 0.02674 0.00438 0.00260 0.00526 AFIX 43 H112 2 0.638403 0.494030 0.590053 -21.00000 -1.20000 AFIX 0 PART 1 C12A 1 0.746538 0.291208 0.487604 21.00000 0.03147 0.03136 = 0.02877 0.00505 0.00946 0.00734 AFIX 43 H121 2 0.924366 0.319802 0.460270 21.00000 -1.20000 AFIX 0 PART 2 C12B 1 0.589966 0.358085 0.472085 -21.00000 0.03477 0.03615 = 0.02808 0.00854 0.00545 0.00404 AFIX 43 H122 2 0.669271 0.433239 0.434938 -21.00000 -1.20000 AFIX 0 PART 0 C13 1 0.495440 0.220532 0.433562 11.00000 0.03730 0.03724 = 0.02217 0.00179 0.00404 0.01072 PART 1 AFIX 43 H131 2 0.505377 0.195620 0.369949 21.00000 -1.20000 PART 2 AFIX 43 H132 2 0.501799 0.198819 0.369442 -21.00000 -1.20000 AFIX 0 PART 1 C14A 1 0.234948 0.186928 0.471745 21.00000 0.03475 0.03453 = 0.02842 0.00013 0.00203 0.00612 AFIX 43 H141 2 0.062719 0.144981 0.433782 21.00000 -1.20000 AFIX 0 PART 2 C14B 1 0.383456 0.104963 0.490020 -21.00000 0.03404 0.02701 = 0.02831 -0.00129 0.00323 0.00546 AFIX 43 H142 2 0.321559 0.005754 0.463919 -21.00000 -1.20000 AFIX 0 PART 1 C15A 1 0.221186 0.213864 0.565743 21.00000 0.02937 0.03215 = 0.02833 0.00207 0.00647 0.00400 AFIX 43 H151 2 0.042145 0.184157 0.592197 21.00000 -1.20000 AFIX 0 PART 2 C15B 1 0.367197 0.140327 0.582791 -21.00000 0.02997 0.02896 = 0.02530 0.00459 0.00512 0.00646 AFIX 43 H152 2 0.286210 0.065741 0.620075 -21.00000 -1.20000 PART 0 AFIX 0 HKLF 4 REM emam16_a.res in P-1 REM wR2 = 0.0888, GooF = S = 1.024, Restrained GooF = 1.024 for all data REM R1 = 0.0327 for 2219 Fo > 4sig(Fo) and 0.0383 for all 2524 data REM 205 parameters refined using 0 restraints END WGHT 0.0485 0.1743 REM Highest difference peak 0.303, deepest hole -0.311, 1-sigma level 0.041 Q1 1 -0.1396 0.0573 0.8577 11.00000 0.05 0.30 Q2 1 0.5071 0.3941 0.7441 11.00000 0.05 0.23 Q3 1 0.4476 0.3046 0.6660 11.00000 0.05 0.20 Q4 1 0.5980 0.4513 0.8144 11.00000 0.05 0.18 Q5 1 0.2810 0.3256 0.8758 11.00000 0.05 0.18 Q6 1 0.4571 0.4197 0.8829 11.00000 0.05 0.17 Q7 1 -0.1116 0.2470 0.9400 11.00000 0.05 0.16 Q8 1 1.0637 0.5719 0.7372 11.00000 0.05 0.16 Q9 1 0.4085 0.2239 0.6015 11.00000 0.05 0.16 Q10 1 0.9269 0.6562 0.7189 11.00000 0.05 0.15 Q11 1 -0.3592 0.1458 0.9011 11.00000 0.05 0.14 Q12 1 0.2183 0.2490 0.7968 11.00000 0.05 0.14 Q13 1 -0.5005 -0.2238 0.8064 11.00000 0.05 0.14 Q14 1 0.9180 0.6273 0.7571 11.00000 0.05 0.13 Q15 1 0.6241 0.5595 0.8991 11.00000 0.05 0.13 Q16 1 0.5664 0.2871 0.4561 11.00000 0.05 0.13 Q17 1 0.1738 0.1426 0.7278 11.00000 0.05 0.12 Q18 1 0.7651 0.5384 0.9225 11.00000 0.05 0.12 Q19 1 0.4171 0.1430 0.8937 11.00000 0.05 0.12 Q20 1 0.1635 0.1353 0.9023 11.00000 0.05 0.12 ; _shelx_res_checksum 11550