#------------------------------------------------------------------------------ #$Date: 2020-05-04 22:27:52 +0300 (Mon, 04 May 2020) $ #$Revision: 251497 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240443.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7240443 loop_ _publ_author_name 'Hadian, Mojgan' 'Shaabani, Shabnam' 'Patil, Pravin' 'Shishkina, Svitlana V.' 'B\"oltz, Harry' 'D\"omling, Alexander' _publ_section_title ; Sustainability by design: automated nanoscale 2,3,4-trisubstituted quinazoline diversity ; _journal_issue 8 _journal_name_full 'Green Chemistry' _journal_page_first 2459 _journal_paper_doi 10.1039/D0GC00363H _journal_volume 22 _journal_year 2020 _chemical_formula_sum 'C11 H11 N O4 S' _chemical_formula_weight 253.27 _space_group_crystal_system orthorhombic _space_group_IT_number 33 _space_group_name_Hall 'P 2c -2n' _space_group_name_H-M_alt 'P n a 21' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2019-11-29 deposited with the CCDC. 2020-02-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 38.544(4) _cell_length_b 5.1102(9) _cell_length_c 11.6487(18) _cell_measurement_reflns_used 1801 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 20.490 _cell_measurement_theta_min 3.622 _cell_volume 2294.4(6) _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.1827 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1215 _diffrn_reflns_av_unetI/netI 0.1042 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 54 _diffrn_reflns_limit_h_min -54 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 22235 _diffrn_reflns_point_group_measured_fraction_full 0.864 _diffrn_reflns_point_group_measured_fraction_max 0.862 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.998 _diffrn_reflns_theta_min 3.171 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.284 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.68438 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.466 _exptl_crystal_description parallelepiped _exptl_crystal_F_000 1056 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.190 _refine_diff_density_max 0.623 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.067 _refine_ls_abs_structure_details ; Flack x determined using 647 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.34(13) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.934 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 309 _refine_ls_number_reflns 5762 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.934 _refine_ls_R_factor_all 0.1406 _refine_ls_R_factor_gt 0.0712 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details '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 0.1668 _refine_ls_wR_factor_ref 0.2128 _reflns_Friedel_coverage 0.651 _reflns_Friedel_fraction_full 0.715 _reflns_Friedel_fraction_max 0.713 _reflns_number_gt 2728 _reflns_number_total 5762 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0gc00363h2.cif _cod_data_source_block add23 _cod_database_code 7240443 _shelx_shelxl_version_number 2016/6 _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. ; _shelx_estimated_absorpt_t_min 0.945 _shelx_estimated_absorpt_t_max 0.948 _shelx_res_file ; TITL add23_a.res in Pna2(1) add23.res created by SHELXL-2016/6 at 18:22:38 on 10-Jul-2019 CELL 0.71073 38.5443 5.1102 11.6487 90 90 90 ZERR 8 0.0039 0.0009 0.0018 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,+Z SYMM 0.5-X,0.5+Y,0.5+Z SFAC C H N O S UNIT 88 88 8 32 8 L.S. 4 PLAN 20 BOND $H list 4 fmap 2 ACTA OMIT 0 60 conf size 0.2 0.2 0.19 temp 20 htab n1a o1a htab n1b o1b eqiv $1 0.5-x,-0.5+y,0.5+z htab o4a o2a_$1 eqiv $2 1-x,2-y,0.5+z htab o4b o2b_$2 WGHT 0.092500 FVAR 0.61180 S1A 5 0.295734 0.093752 0.180938 11.00000 0.05566 0.05482 = 0.09085 0.00991 0.00657 -0.00237 O1A 4 0.367640 0.263938 0.354779 11.00000 0.08307 0.08227 = 0.07518 0.01818 -0.00115 0.00614 O2A 4 0.331691 0.661784 -0.014039 11.00000 0.05679 0.07170 = 0.06885 0.01279 -0.01189 -0.00687 O3A 4 0.252581 0.005200 0.379614 11.00000 0.06574 0.14449 = 0.18418 0.08678 0.03621 0.02111 O4A 4 0.217385 0.335291 0.348104 11.00000 0.08091 0.06447 = 0.09431 0.00930 0.03162 0.00967 AFIX 147 H4OA 2 0.206904 0.274878 0.403331 11.00000 -1.50000 AFIX 0 N1A 3 0.353743 0.490775 0.150086 11.00000 0.04603 0.05388 = 0.05762 0.00794 -0.00646 0.00038 AFIX 43 H1NA 2 0.350179 0.370280 0.200258 11.00000 -1.20000 AFIX 0 C1A 1 0.381719 0.657955 0.172772 11.00000 0.04047 0.05650 = 0.06061 -0.00139 0.00158 0.00345 C2A 1 0.392142 0.852587 0.098585 11.00000 0.04155 0.06773 = 0.07987 0.00333 -0.00274 -0.00302 AFIX 43 H2A 2 0.380325 0.877787 0.029861 11.00000 -1.20000 AFIX 0 C3A 1 0.420324 1.012120 0.125962 11.00000 0.05246 0.06946 = 0.08700 -0.00219 0.01328 -0.00111 AFIX 43 H3A 2 0.426450 1.148195 0.076976 11.00000 -1.20000 AFIX 0 C4A 1 0.439118 0.970502 0.224401 11.00000 0.05089 0.07794 = 0.10408 -0.01889 -0.00241 -0.00884 AFIX 43 H4A 2 0.458317 1.073855 0.241212 11.00000 -1.20000 AFIX 0 C5A 1 0.429124 0.773808 0.297695 11.00000 0.04654 0.08164 = 0.07979 -0.02606 -0.01474 0.01008 AFIX 43 H5A 2 0.441940 0.746877 0.364299 11.00000 -1.20000 AFIX 0 C6A 1 0.400708 0.613256 0.276724 11.00000 0.03906 0.07006 = 0.06188 -0.01343 -0.00290 0.01356 C7A 1 0.391837 0.415369 0.360029 11.00000 0.07224 0.08842 = 0.05711 0.00092 -0.00670 0.02859 AFIX 43 H7A 2 0.406094 0.402577 0.424193 11.00000 -1.20000 AFIX 0 C8A 1 0.331942 0.492843 0.061607 11.00000 0.04430 0.05073 = 0.05085 -0.00665 -0.00119 0.00392 C9A 1 0.306781 0.266884 0.051998 11.00000 0.06151 0.06526 = 0.07144 0.00059 0.00002 -0.01581 AFIX 23 H9AA 2 0.316408 0.141600 -0.001841 11.00000 -1.20000 H9AB 2 0.285463 0.333113 0.018619 11.00000 -1.20000 AFIX 0 C10A 1 0.269565 0.338789 0.248710 11.00000 0.08930 0.07914 = 0.12231 0.00546 0.04615 -0.00495 AFIX 23 H10A 2 0.284314 0.466712 0.286168 11.00000 -1.20000 H10B 2 0.255665 0.428613 0.191562 11.00000 -1.20000 AFIX 0 C11A 1 0.246445 0.211596 0.335220 11.00000 0.05660 0.06831 = 0.10066 0.00903 0.02074 -0.00329 S1B 5 0.478169 0.503620 0.782078 11.00000 0.05743 0.04086 = 0.05423 -0.00353 -0.00649 0.00289 O1B 4 0.392824 0.247710 0.828867 11.00000 0.08968 0.08506 = 0.08766 0.02541 0.00890 -0.01190 O2B 4 0.426617 1.008659 0.586525 11.00000 0.04789 0.05536 = 0.06848 0.01926 -0.00173 -0.00131 O3B 4 0.495320 1.026828 0.954166 11.00000 0.07652 0.04844 = 0.07364 0.00247 -0.02094 -0.00425 O4B 4 0.523524 0.677682 1.014854 11.00000 0.06050 0.04765 = 0.06572 0.00164 -0.01899 -0.00061 AFIX 147 H4OB 2 0.538969 0.785166 1.025816 11.00000 -1.50000 AFIX 0 N1B 3 0.407826 0.645121 0.679820 11.00000 0.05193 0.04617 = 0.06552 0.00907 -0.00267 -0.00615 AFIX 43 H1NB 2 0.414680 0.523703 0.725635 11.00000 -1.20000 AFIX 0 C1B 1 0.373041 0.626556 0.644860 11.00000 0.04916 0.04904 = 0.05954 -0.00603 0.00368 -0.00299 C2B 1 0.359027 0.789681 0.560557 11.00000 0.04936 0.06138 = 0.08150 -0.00127 -0.00570 0.00060 AFIX 43 H2B 2 0.372509 0.920769 0.527741 11.00000 -1.20000 AFIX 0 C3B 1 0.325156 0.755340 0.526322 11.00000 0.05247 0.07902 = 0.09529 -0.01203 -0.01641 0.00829 AFIX 43 H3B 2 0.315866 0.865306 0.470629 11.00000 -1.20000 AFIX 0 C4B 1 0.304963 0.563271 0.572467 11.00000 0.04503 0.11185 = 0.11591 -0.02456 -0.00577 0.00012 AFIX 43 H4B 2 0.282246 0.541756 0.547277 11.00000 -1.20000 AFIX 0 C5B 1 0.318105 0.400760 0.656373 11.00000 0.05412 0.08441 = 0.10395 -0.02020 0.01756 -0.01395 AFIX 43 H5B 2 0.304003 0.272200 0.688242 11.00000 -1.20000 AFIX 0 C6B 1 0.352512 0.426922 0.694307 11.00000 0.05732 0.05605 = 0.07860 -0.01181 0.01424 -0.00890 C7B 1 0.364815 0.251346 0.783236 11.00000 0.08423 0.06472 = 0.08547 -0.00287 0.03773 -0.01920 AFIX 43 H7B 2 0.349071 0.125677 0.808154 11.00000 -1.20000 AFIX 0 C8B 1 0.431894 0.823052 0.652632 11.00000 0.05006 0.04191 = 0.05732 0.00045 0.00199 -0.00285 C9B 1 0.468052 0.790888 0.699321 11.00000 0.04867 0.04958 = 0.05369 0.00451 -0.00647 -0.00538 AFIX 23 H9BA 2 0.473030 0.942230 0.746806 11.00000 -1.20000 H9BB 2 0.483957 0.796513 0.634836 11.00000 -1.20000 AFIX 0 C10B 1 0.469126 0.613022 0.926816 11.00000 0.05517 0.04316 = 0.05453 -0.00624 -0.00066 -0.00298 AFIX 23 H10C 2 0.446932 0.702403 0.928686 11.00000 -1.20000 H10D 2 0.467803 0.463201 0.977758 11.00000 -1.20000 AFIX 0 C11B 1 0.496892 0.793301 0.966636 11.00000 0.05959 0.04465 = 0.03892 0.00086 -0.00148 -0.00499 HKLF 4 REM add23_a.res in Pna2(1) REM R1 = 0.0712 for 2728 Fo > 4sig(Fo) and 0.1406 for all 5762 data REM 309 parameters refined using 1 restraints END WGHT 0.0930 0.0000 REM Highest difference peak 0.623, deepest hole -0.338, 1-sigma level 0.067 Q1 1 0.2933 -0.0935 0.1804 11.00000 0.05 0.33 Q2 1 0.4728 0.8137 0.7787 11.00000 0.05 0.27 Q3 1 0.4803 0.3217 0.7624 11.00000 0.05 0.26 Q4 1 0.4320 0.4935 0.2879 11.00000 0.05 0.24 Q5 1 0.3016 0.4138 0.0787 11.00000 0.05 0.24 Q6 1 0.4998 1.1560 0.7322 11.00000 0.05 0.23 Q7 1 0.4826 0.9196 1.0833 11.00000 0.05 0.23 Q8 1 0.4715 1.1881 0.7839 11.00000 0.05 0.22 Q9 1 0.4713 1.1886 0.6813 11.00000 0.05 0.22 Q10 1 0.2960 0.1218 0.3903 11.00000 0.05 0.22 Q11 1 0.4556 0.7454 0.1076 11.00000 0.05 0.22 Q12 1 0.4306 1.1752 0.6490 11.00000 0.05 0.21 Q13 1 0.3908 0.7386 0.4130 11.00000 0.05 0.21 Q14 1 0.3647 0.3205 0.3710 11.00000 0.05 0.21 Q15 1 0.2796 0.5304 0.2210 11.00000 0.05 0.20 Q16 1 0.4016 0.5147 0.0975 11.00000 0.05 0.20 Q17 1 0.4586 0.5586 0.6972 11.00000 0.05 0.20 Q18 1 0.5301 0.4321 0.9330 11.00000 0.05 0.20 Q19 1 0.2745 -0.1491 0.2610 11.00000 0.05 0.19 Q20 1 0.2971 0.0309 -0.0362 11.00000 0.05 0.19 ; _shelx_res_checksum 73552 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' 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 S1A S 0.29573(5) 0.0938(3) 0.1809(2) 0.0671(6) Uani 1 1 d . . . . . O1A O 0.36764(18) 0.2639(11) 0.3548(5) 0.0802(16) Uani 1 1 d . . . . . O2A O 0.33169(13) 0.6618(10) -0.0140(5) 0.0658(13) Uani 1 1 d . . . . . O3A O 0.25258(19) 0.0052(14) 0.3796(9) 0.131(4) Uani 1 1 d . . . . . O4A O 0.21739(16) 0.3353(10) 0.3481(6) 0.0799(17) Uani 1 1 d . . . . . H4OA H 0.206904 0.274878 0.403331 0.120 Uiso 1 1 calc R U . . . N1A N 0.35374(15) 0.4908(9) 0.1501(5) 0.0525(13) Uani 1 1 d . . . . . H1NA H 0.350179 0.370280 0.200258 0.063 Uiso 1 1 calc R U . . . C1A C 0.38172(17) 0.6580(12) 0.1728(6) 0.0525(15) Uani 1 1 d . . . . . C2A C 0.39214(19) 0.8526(14) 0.0986(8) 0.0630(18) Uani 1 1 d . . . . . H2A H 0.380325 0.877787 0.029861 0.076 Uiso 1 1 calc R U . . . C3A C 0.4203(2) 1.0121(15) 0.1260(9) 0.070(2) Uani 1 1 d . . . . . H3A H 0.426450 1.148195 0.076976 0.084 Uiso 1 1 calc R U . . . C4A C 0.4391(2) 0.9705(16) 0.2244(9) 0.078(2) Uani 1 1 d . . . . . H4A H 0.458317 1.073855 0.241212 0.093 Uiso 1 1 calc R U . . . C5A C 0.4291(2) 0.7738(14) 0.2977(8) 0.069(2) Uani 1 1 d . . . . . H5A H 0.441940 0.746877 0.364299 0.083 Uiso 1 1 calc R U . . . C6A C 0.40071(17) 0.6133(13) 0.2767(7) 0.0570(16) Uani 1 1 d . . . . . C7A C 0.3918(2) 0.4154(17) 0.3600(7) 0.073(2) Uani 1 1 d . . . . . H7A H 0.406094 0.402577 0.424193 0.087 Uiso 1 1 calc R U . . . C8A C 0.33194(17) 0.4928(12) 0.0616(6) 0.0486(15) Uani 1 1 d . . . . . C9A C 0.3068(2) 0.2669(15) 0.0520(7) 0.066(2) Uani 1 1 d . . . . . H9AA H 0.316408 0.141600 -0.001841 0.079 Uiso 1 1 calc R U . . . H9AB H 0.285463 0.333113 0.018619 0.079 Uiso 1 1 calc R U . . . C10A C 0.2696(3) 0.3388(16) 0.2487(10) 0.097(3) Uani 1 1 d . . . . . H10A H 0.284314 0.466712 0.286168 0.116 Uiso 1 1 calc R U . . . H10B H 0.255665 0.428613 0.191562 0.116 Uiso 1 1 calc R U . . . C11A C 0.2464(2) 0.2116(16) 0.3352(9) 0.075(2) Uani 1 1 d . . . . . S1B S 0.47817(4) 0.5036(3) 0.78208(18) 0.0508(4) Uani 1 1 d . . . . . O1B O 0.39282(19) 0.2477(11) 0.8289(6) 0.0875(19) Uani 1 1 d . . . . . O2B O 0.42662(12) 1.0087(8) 0.5865(4) 0.0572(12) Uani 1 1 d . . . . . O3B O 0.49532(16) 1.0268(9) 0.9542(5) 0.0662(14) Uani 1 1 d . . . . . O4B O 0.52352(13) 0.6777(8) 1.0149(4) 0.0580(12) Uani 1 1 d . . . . . H4OB H 0.538969 0.785166 1.025816 0.087 Uiso 1 1 calc R U . . . N1B N 0.40783(14) 0.6451(9) 0.6798(5) 0.0545(13) Uani 1 1 d . . . . . H1NB H 0.414680 0.523703 0.725635 0.065 Uiso 1 1 calc R U . . . C1B C 0.37304(18) 0.6266(12) 0.6449(6) 0.0526(16) Uani 1 1 d . . . . . C2B C 0.3590(2) 0.7897(14) 0.5606(7) 0.0641(19) Uani 1 1 d . . . . . H2B H 0.372509 0.920769 0.527741 0.077 Uiso 1 1 calc R U . . . C3B C 0.3252(2) 0.7553(17) 0.5263(9) 0.076(2) Uani 1 1 d . . . . . H3B H 0.315866 0.865306 0.470629 0.091 Uiso 1 1 calc R U . . . C4B C 0.3050(2) 0.563(2) 0.5725(10) 0.091(3) Uani 1 1 d . . . . . H4B H 0.282246 0.541756 0.547277 0.109 Uiso 1 1 calc R U . . . C5B C 0.3181(2) 0.4008(18) 0.6564(10) 0.081(3) Uani 1 1 d . . . . . H5B H 0.304003 0.272200 0.688242 0.097 Uiso 1 1 calc R U . . . C6B C 0.3525(2) 0.4269(13) 0.6943(7) 0.0640(19) Uani 1 1 d . . . . . C7B C 0.3648(3) 0.2513(15) 0.7832(9) 0.078(3) Uani 1 1 d . . . . . H7B H 0.349071 0.125677 0.808154 0.094 Uiso 1 1 calc R U . . . C8B C 0.43189(18) 0.8231(11) 0.6526(6) 0.0498(15) Uani 1 1 d . . . . . C9B C 0.46805(17) 0.7909(11) 0.6993(6) 0.0506(15) Uani 1 1 d . . . . . H9BA H 0.473030 0.942230 0.746806 0.061 Uiso 1 1 calc R U . . . H9BB H 0.483957 0.796513 0.634836 0.061 Uiso 1 1 calc R U . . . C10B C 0.46913(18) 0.6130(12) 0.9268(6) 0.0510(15) Uani 1 1 d . . . . . H10C H 0.446932 0.702403 0.928686 0.061 Uiso 1 1 calc R U . . . H10D H 0.467803 0.463201 0.977758 0.061 Uiso 1 1 calc R U . . . C11B C 0.49689(19) 0.7933(11) 0.9666(6) 0.0477(14) 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 S1A 0.0557(10) 0.0548(9) 0.0909(14) 0.0099(10) 0.0066(11) -0.0024(8) O1A 0.083(4) 0.082(3) 0.075(4) 0.018(3) -0.001(3) 0.006(3) O2A 0.057(3) 0.072(3) 0.069(3) 0.013(3) -0.012(3) -0.007(2) O3A 0.066(5) 0.144(6) 0.184(9) 0.087(7) 0.036(5) 0.021(4) O4A 0.081(4) 0.064(3) 0.094(4) 0.009(3) 0.032(4) 0.010(3) N1A 0.046(3) 0.054(3) 0.058(3) 0.008(3) -0.006(3) 0.000(2) C1A 0.040(3) 0.057(3) 0.061(4) -0.001(3) 0.002(3) 0.003(3) C2A 0.042(4) 0.068(4) 0.080(5) 0.003(4) -0.003(4) -0.003(3) C3A 0.052(5) 0.069(5) 0.087(6) -0.002(4) 0.013(4) -0.001(4) C4A 0.051(5) 0.078(5) 0.104(7) -0.019(5) -0.002(5) -0.009(4) C5A 0.047(4) 0.082(4) 0.080(5) -0.026(4) -0.015(4) 0.010(4) C6A 0.039(3) 0.070(4) 0.062(4) -0.013(4) -0.003(3) 0.014(3) C7A 0.072(6) 0.088(5) 0.057(4) 0.001(4) -0.007(4) 0.029(5) C8A 0.044(4) 0.051(3) 0.051(4) -0.007(3) -0.001(3) 0.004(3) C9A 0.062(5) 0.065(4) 0.071(6) 0.001(4) 0.000(4) -0.016(4) C10A 0.089(7) 0.079(5) 0.122(8) 0.005(5) 0.046(7) -0.005(5) C11A 0.057(5) 0.068(5) 0.101(7) 0.009(4) 0.021(5) -0.003(4) S1B 0.0574(9) 0.0409(7) 0.0542(8) -0.0035(6) -0.0065(8) 0.0029(7) O1B 0.090(5) 0.085(4) 0.088(4) 0.025(3) 0.009(4) -0.012(4) O2B 0.048(3) 0.055(3) 0.068(3) 0.019(2) -0.002(2) -0.001(2) O3B 0.077(4) 0.048(3) 0.074(3) 0.002(2) -0.021(3) -0.004(2) O4B 0.060(3) 0.048(2) 0.066(3) 0.002(2) -0.019(3) -0.001(2) N1B 0.052(3) 0.046(3) 0.066(4) 0.009(3) -0.003(3) -0.006(2) C1B 0.049(4) 0.049(3) 0.060(4) -0.006(3) 0.004(3) -0.003(3) C2B 0.049(4) 0.061(4) 0.082(6) -0.001(4) -0.006(4) 0.001(3) C3B 0.052(5) 0.079(5) 0.095(6) -0.012(4) -0.016(4) 0.008(4) C4B 0.045(5) 0.112(7) 0.116(8) -0.025(7) -0.006(5) 0.000(5) C5B 0.054(5) 0.084(5) 0.104(7) -0.020(5) 0.018(5) -0.014(4) C6B 0.057(4) 0.056(4) 0.079(5) -0.012(4) 0.014(4) -0.009(3) C7B 0.084(7) 0.065(4) 0.085(6) -0.003(4) 0.038(6) -0.019(4) C8B 0.050(4) 0.042(3) 0.057(4) 0.000(3) 0.002(3) -0.003(3) C9B 0.049(4) 0.050(3) 0.054(4) 0.005(3) -0.006(3) -0.005(3) C10B 0.055(4) 0.043(3) 0.055(4) -0.006(3) -0.001(3) -0.003(3) C11B 0.060(4) 0.045(3) 0.039(3) 0.001(3) -0.001(3) -0.005(3) 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' 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 C10A S1A C9A 99.1(4) . . ? C11A O4A H4OA 109.5 . . ? C8A N1A C1A 128.9(6) . . ? C8A N1A H1NA 115.6 . . ? C1A N1A H1NA 115.6 . . ? C2A C1A N1A 123.1(7) . . ? C2A C1A C6A 119.7(6) . . ? N1A C1A C6A 117.1(6) . . ? C1A C2A C3A 120.4(8) . . ? C1A C2A H2A 119.8 . . ? C3A C2A H2A 119.8 . . ? C4A C3A C2A 120.7(8) . . ? C4A C3A H3A 119.6 . . ? C2A C3A H3A 119.6 . . ? C3A C4A C5A 119.0(8) . . ? C3A C4A H4A 120.5 . . ? C5A C4A H4A 120.5 . . ? C4A C5A C6A 122.9(8) . . ? C4A C5A H5A 118.5 . . ? C6A C5A H5A 118.5 . . ? C5A C6A C1A 117.2(7) . . ? C5A C6A C7A 118.8(8) . . ? C1A C6A C7A 124.0(7) . . ? O1A C7A C6A 126.5(8) . . ? O1A C7A H7A 116.7 . . ? C6A C7A H7A 116.7 . . ? O2A C8A N1A 124.3(6) . . ? O2A C8A C9A 118.5(6) . . ? N1A C8A C9A 117.2(6) . . ? C8A C9A S1A 117.8(6) . . ? C8A C9A H9AA 107.9 . . ? S1A C9A H9AA 107.9 . . ? C8A C9A H9AB 107.9 . . ? S1A C9A H9AB 107.9 . . ? H9AA C9A H9AB 107.2 . . ? C11A C10A S1A 109.2(6) . . ? C11A C10A H10A 109.8 . . ? S1A C10A H10A 109.8 . . ? C11A C10A H10B 109.8 . . ? S1A C10A H10B 109.8 . . ? H10A C10A H10B 108.3 . . ? O3A C11A O4A 123.4(8) . . ? O3A C11A C10A 123.8(8) . . ? O4A C11A C10A 112.4(8) . . ? C9B S1B C10B 101.9(3) . . ? C11B O4B H4OB 109.5 . . ? C8B N1B C1B 129.8(6) . . ? C8B N1B H1NB 115.1 . . ? C1B N1B H1NB 115.1 . . ? C2B C1B N1B 122.2(6) . . ? C2B C1B C6B 120.0(7) . . ? N1B C1B C6B 117.7(6) . . ? C3B C2B C1B 119.6(8) . . ? C3B C2B H2B 120.2 . . ? C1B C2B H2B 120.2 . . ? C4B C3B C2B 121.3(9) . . ? C4B C3B H3B 119.4 . . ? C2B C3B H3B 119.4 . . ? C3B C4B C5B 120.2(9) . . ? C3B C4B H4B 119.9 . . ? C5B C4B H4B 119.9 . . ? C4B C5B C6B 120.8(8) . . ? C4B C5B H5B 119.6 . . ? C6B C5B H5B 119.6 . . ? C5B C6B C1B 118.0(8) . . ? C5B C6B C7B 118.3(8) . . ? C1B C6B C7B 123.7(7) . . ? O1B C7B C6B 128.2(7) . . ? O1B C7B H7B 115.9 . . ? C6B C7B H7B 115.9 . . ? O2B C8B N1B 123.6(6) . . ? O2B C8B C9B 117.4(6) . . ? N1B C8B C9B 118.9(6) . . ? C8B C9B S1B 118.9(5) . . ? C8B C9B H9BA 107.6 . . ? S1B C9B H9BA 107.6 . . ? C8B C9B H9BB 107.6 . . ? S1B C9B H9BB 107.6 . . ? H9BA C9B H9BB 107.0 . . ? C11B C10B S1B 110.1(5) . . ? C11B C10B H10C 109.6 . . ? S1B C10B H10C 109.6 . . ? C11B C10B H10D 109.6 . . ? S1B C10B H10D 109.6 . . ? H10C C10B H10D 108.2 . . ? O3B C11B O4B 122.5(6) . . ? O3B C11B C10B 122.7(6) . . ? O4B C11B C10B 114.7(5) . . ? 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 S1A C10A 1.791(9) . ? S1A C9A 1.794(8) . ? O1A C7A 1.213(10) . ? O2A C8A 1.234(8) . ? O3A C11A 1.198(9) . ? O4A C11A 1.295(10) . ? O4A H4OA 0.8200 . ? N1A C8A 1.330(8) . ? N1A C1A 1.401(8) . ? N1A H1NA 0.8600 . ? C1A C2A 1.377(10) . ? C1A C6A 1.433(10) . ? C2A C3A 1.395(10) . ? C2A H2A 0.9300 . ? C3A C4A 1.373(13) . ? C3A H3A 0.9300 . ? C4A C5A 1.374(12) . ? C4A H4A 0.9300 . ? C5A C6A 1.390(10) . ? C5A H5A 0.9300 . ? C6A C7A 1.443(11) . ? C7A H7A 0.9300 . ? C8A C9A 1.512(9) . ? C9A H9AA 0.9700 . ? C9A H9AB 0.9700 . ? C10A C11A 1.494(12) . ? C10A H10A 0.9700 . ? C10A H10B 0.9700 . ? S1B C9B 1.799(6) . ? S1B C10B 1.810(7) . ? O1B C7B 1.204(11) . ? O2B C8B 1.239(7) . ? O3B C11B 1.204(7) . ? O4B C11B 1.311(8) . ? O4B H4OB 0.8200 . ? N1B C8B 1.337(8) . ? N1B C1B 1.404(9) . ? N1B H1NB 0.8600 . ? C1B C2B 1.397(10) . ? C1B C6B 1.414(10) . ? C2B C3B 1.376(10) . ? C2B H2B 0.9300 . ? C3B C4B 1.363(14) . ? C3B H3B 0.9300 . ? C4B C5B 1.379(14) . ? C4B H4B 0.9300 . ? C5B C6B 1.404(12) . ? C5B H5B 0.9300 . ? C6B C7B 1.450(13) . ? C7B H7B 0.9300 . ? C8B C9B 1.505(9) . ? C9B H9BA 0.9700 . ? C9B H9BB 0.9700 . ? C10B C11B 1.486(9) . ? C10B H10C 0.9700 . ? C10B H10D 0.9700 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1A H1NA O1A 0.86 2.00 2.705(8) 138.9 . N1B H1NB O1B 0.86 2.04 2.734(8) 137.7 . O4A H4OA O2A 0.82 1.86 2.635(8) 156.2 4_545 O4B H4OB O2B 0.82 1.84 2.638(6) 165.7 2_675 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 C8A N1A C1A C2A -3.4(11) . . . . ? C8A N1A C1A C6A 179.0(6) . . . . ? N1A C1A C2A C3A -179.7(7) . . . . ? C6A C1A C2A C3A -2.2(11) . . . . ? C1A C2A C3A C4A 3.0(12) . . . . ? C2A C3A C4A C5A -2.0(12) . . . . ? C3A C4A C5A C6A 0.1(12) . . . . ? C4A C5A C6A C1A 0.6(11) . . . . ? C4A C5A C6A C7A -178.7(7) . . . . ? C2A C1A C6A C5A 0.4(10) . . . . ? N1A C1A C6A C5A 178.1(6) . . . . ? C2A C1A C6A C7A 179.8(7) . . . . ? N1A C1A C6A C7A -2.6(9) . . . . ? C5A C6A C7A O1A 178.8(8) . . . . ? C1A C6A C7A O1A -0.5(12) . . . . ? C1A N1A C8A O2A -5.2(11) . . . . ? C1A N1A C8A C9A 172.6(7) . . . . ? O2A C8A C9A S1A -157.6(6) . . . . ? N1A C8A C9A S1A 24.5(9) . . . . ? C10A S1A C9A C8A 71.4(8) . . . . ? C9A S1A C10A C11A 158.7(8) . . . . ? S1A C10A C11A O3A 23.6(14) . . . . ? S1A C10A C11A O4A -149.7(7) . . . . ? C8B N1B C1B C2B 7.6(11) . . . . ? C8B N1B C1B C6B -175.2(7) . . . . ? N1B C1B C2B C3B 177.3(7) . . . . ? C6B C1B C2B C3B 0.2(11) . . . . ? C1B C2B C3B C4B -0.5(13) . . . . ? C2B C3B C4B C5B 1.0(15) . . . . ? C3B C4B C5B C6B -1.1(15) . . . . ? C4B C5B C6B C1B 0.7(12) . . . . ? C4B C5B C6B C7B 179.7(8) . . . . ? C2B C1B C6B C5B -0.3(11) . . . . ? N1B C1B C6B C5B -177.5(7) . . . . ? C2B C1B C6B C7B -179.2(7) . . . . ? N1B C1B C6B C7B 3.6(10) . . . . ? C5B C6B C7B O1B -177.7(9) . . . . ? C1B C6B C7B O1B 1.1(13) . . . . ? C1B N1B C8B O2B -1.1(12) . . . . ? C1B N1B C8B C9B -177.8(6) . . . . ? O2B C8B C9B S1B -172.9(5) . . . . ? N1B C8B C9B S1B 4.0(9) . . . . ? C10B S1B C9B C8B -91.7(6) . . . . ? C9B S1B C10B C11B -74.0(5) . . . . ? S1B C10B C11B O3B 91.3(8) . . . . ? S1B C10B C11B O4B -87.7(6) . . . . ?