#------------------------------------------------------------------------------ #$Date: 2023-11-11 01:57:02 +0200 (Sat, 11 Nov 2023) $ #$Revision: 287527 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247701.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_7247701 loop_ _publ_author_name 'Ahmed, Muhammad Naeem' 'Akhtar, Maheen' 'Andleeb, Hina' 'Bashir, Muhammad Adnan' 'Ibrahim, Mahmoud A. A.' 'Sidhom, Peter' 'Arshad, Ifzan' 'Tahir, Muhammad Nawaz' 'Gil, Diego Mauricio' 'Gomila, Rosa Maria' 'Frontera, Antonio' _publ_section_title ; Crystal engineering with 1,3,4-oxadiazoles derivatives: On the importance of CH···N and CH···\p interactions ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D3CE00944K _journal_year 2023 _chemical_formula_iupac 'C22 H26 N2 O4 S' _chemical_formula_moiety 'C22 H26 N2 O4 S' _chemical_formula_sum 'C22 H26 N2 O4 S' _chemical_formula_weight 414.51 _chemical_name_systematic 2-[(4-Tertbutylphenylmethyl)sulfanyl]-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2019/2 _audit_update_record ; 2023-10-06 deposited with the CCDC. 2023-10-23 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 97.9360(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.40660(10) _cell_length_b 24.9033(2) _cell_length_c 8.87920(10) _cell_measurement_reflns_used 4266 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 77.005 _cell_measurement_theta_min 4.290 _cell_volume 2279.08(4) _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)' _computing_publication_material ; WinGX (Farrugia, 1999) and PLATON (Spek, 2009) ; _computing_structure_refinement 'SHELXL-2019/2 (Sheldrick, 2019)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 296(2) _diffrn_detector_area_resol_mean 8.16 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB AFC11 (RINC): quarter-chi single' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_unetI/netI 0.0171 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 31041 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 70.975 _diffrn_reflns_theta_min 4.290 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.497 _exptl_absorpt_correction_T_max 0.615 _exptl_absorpt_correction_T_min 0.545 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022) Empirical absorption correctionusing spherical harmonics, implimented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'light yellow' _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_description rod _exptl_crystal_F_000 880 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _refine_diff_density_max 0.312 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.034 _refine_ls_extinction_coef 0.0015(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2019/2 (Sheldrick 2019)' _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 286 _refine_ls_number_reflns 4391 _refine_ls_number_restraints 14 _refine_ls_restrained_S_all 1.112 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0454 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0771P)^2^+0.4386P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1342 _refine_ls_wR_factor_ref 0.1372 _reflns_number_gt 4023 _reflns_number_total 4391 _reflns_threshold_expression I>2\s(I) _cod_data_source_file d3ce00944k2.cif _cod_data_source_block 9_AUTO _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7247701 _shelx_shelxl_version_number 2019/2 _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 0.615 _shelx_estimated_absorpt_t_max 0.774 _shelx_res_file ; TITL 9_auto_a.res in P2(1)/c LIGHT YELLOW ROD shelx.res created by SHELXL-2019/2 at 14:06:18 on 05-Oct-2023 CELL 1.54184 10.4066 24.9033 8.8792 90.000 97.936 90.000 ZERR 4.00 0.0001 0.0002 0.0001 0.000 0.001 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O S UNIT 88 104 8 16 4 ACTA OMIT -2 142 L.S. 50 TEMP 23.00 MERG 2 MORE -1 FMAP 2 PLAN 10 BOND $H HTAB CONF LIST 4 OMIT 0 2 0 DFIX 1.47 0.01 O3 C21A O3 C21B DFIX 1.51 0.01 C10 C11A C10 C12A C10 C13A DANG 2.50 0.02 C11A C12A C12A C13A C13A C11A DFIX 1.51 0.01 C10 C11B C10 C12B C10 C13B DANG 2.50 0.02 C11B C12B C12B C13B C13B C11B EADP C11A C11B EADP C12A C12B EADP C13A C13B EADP C21A C21B MPLA 6 C14 C15 C16 C17 C18 C19 MPLA 6 C1 C2 N1 N2 O1 S1 MPLA 7 C3 C4 C5 C6 C7 C8 C9 C10 MPLA 6 C14 C15 C16 C17 C18 C19 SIZE 0.36 0.28 0.24 HTAB C21A O2 WGHT 0.077100 0.438600 EXTI 0.001472 FVAR 0.79596 0.69854 S1 5 0.656654 0.374507 0.600502 11.00000 0.10863 0.05407 = 0.05061 -0.00483 -0.00837 0.01371 O1 4 0.533070 0.388932 0.322206 11.00000 0.07809 0.04432 = 0.04962 0.00001 -0.00213 0.00639 O2 4 0.279837 0.511335 -0.078829 11.00000 0.12883 0.05013 = 0.07771 -0.00170 -0.01277 0.02891 O3 4 0.225958 0.450393 -0.329290 11.00000 0.10855 0.06441 = 0.07270 0.00836 -0.02627 0.01558 O4 4 0.303422 0.349631 -0.336067 11.00000 0.10927 0.05822 = 0.06317 -0.00968 -0.02414 0.01644 N1 3 0.593655 0.304761 0.365161 11.00000 0.08695 0.04835 = 0.05184 0.00256 -0.00385 0.00806 N2 3 0.530993 0.309460 0.214136 11.00000 0.07708 0.04684 = 0.05262 0.00105 -0.00376 0.00442 C1 1 0.592069 0.352133 0.421581 11.00000 0.06978 0.04899 = 0.04719 0.00435 0.00273 0.00481 C2 1 0.497756 0.358745 0.194337 11.00000 0.05384 0.04484 = 0.04910 0.00022 0.00540 -0.00082 C3 1 0.745864 0.313926 0.666957 11.00000 0.09025 0.05622 = 0.05167 -0.00196 -0.00404 0.01094 AFIX 23 H3A 2 0.686023 0.284476 0.674222 11.00000 -1.20000 H3B 2 0.804805 0.303821 0.596183 11.00000 -1.20000 AFIX 0 C4 1 0.820718 0.325676 0.820635 11.00000 0.07187 0.05172 = 0.04968 -0.00044 0.00110 0.00641 C5 1 0.770403 0.311918 0.951530 11.00000 0.06142 0.04966 = 0.05819 0.00521 -0.00024 -0.00512 AFIX 43 H5 2 0.689902 0.295177 0.944311 11.00000 -1.20000 AFIX 0 C6 1 0.838454 0.322784 1.092698 11.00000 0.05979 0.06492 = 0.04980 0.00661 0.00577 -0.00451 AFIX 43 H6 2 0.802074 0.313355 1.178939 11.00000 -1.20000 AFIX 0 C7 1 0.958504 0.347131 1.110447 11.00000 0.05378 0.07986 = 0.05428 -0.00349 0.00580 -0.00306 C8 1 1.008239 0.360457 0.978444 11.00000 0.06038 0.12361 = 0.06655 -0.00490 0.01416 -0.02308 AFIX 43 H8 2 1.089394 0.376651 0.985843 11.00000 -1.20000 AFIX 0 C9 1 0.940768 0.350383 0.836272 11.00000 0.07787 0.10690 = 0.05574 -0.00013 0.01930 -0.01147 AFIX 43 H9 2 0.976482 0.360331 0.750001 11.00000 -1.20000 AFIX 0 C10 1 1.029804 0.359203 1.269368 11.00000 0.06398 0.12903 = 0.06467 -0.01724 -0.00326 -0.00974 PART 1 C11A 1 0.953582 0.399176 1.347275 21.00000 0.12678 0.16388 = 0.07545 -0.04540 -0.00580 0.00178 AFIX 137 H11A 2 0.865225 0.387334 1.341149 21.00000 -1.50000 H11B 2 0.956089 0.433483 1.298461 21.00000 -1.50000 H11C 2 0.990653 0.402293 1.452073 21.00000 -1.50000 AFIX 0 C12A 1 1.024275 0.305946 1.375926 21.00000 0.10875 0.15209 = 0.06377 0.02822 -0.01257 -0.02219 AFIX 137 H12A 2 0.935496 0.295739 1.377360 21.00000 -1.50000 H12B 2 1.064139 0.313815 1.477567 21.00000 -1.50000 H12C 2 1.069944 0.277012 1.335426 21.00000 -1.50000 AFIX 0 C13A 1 1.171434 0.370784 1.277922 21.00000 0.07421 0.16748 = 0.07442 0.00416 -0.01232 -0.04611 AFIX 137 H13A 2 1.211964 0.343139 1.225621 21.00000 -1.50000 H13B 2 1.210110 0.371805 1.382495 21.00000 -1.50000 H13C 2 1.183269 0.404853 1.231148 21.00000 -1.50000 AFIX 0 PART 2 C11B 1 1.047556 0.424621 1.256102 -21.00000 0.12678 0.16388 = 0.07545 -0.04540 -0.00580 0.00178 AFIX 137 H11D 2 1.120179 0.432209 1.203589 -21.00000 -1.50000 H11E 2 1.062505 0.439968 1.356171 -21.00000 -1.50000 H11F 2 0.970341 0.439848 1.200808 -21.00000 -1.50000 AFIX 0 C12B 1 0.965974 0.348559 1.395249 -21.00000 0.10875 0.15209 = 0.06377 0.02822 -0.01257 -0.02219 AFIX 137 H12D 2 0.892542 0.372013 1.393196 -21.00000 -1.50000 H12E 2 1.024558 0.354467 1.487132 -21.00000 -1.50000 H12F 2 0.937118 0.311908 1.391609 -21.00000 -1.50000 AFIX 0 C13B 1 1.165450 0.339438 1.265696 -21.00000 0.07421 0.16748 = 0.07442 0.00416 -0.01232 -0.04611 AFIX 137 H13D 2 1.193989 0.350073 1.171814 -21.00000 -1.50000 H13E 2 1.167103 0.300989 1.273512 -21.00000 -1.50000 H13F 2 1.222097 0.354599 1.349412 -21.00000 -1.50000 PART 0 AFIX 0 C14 1 0.429678 0.383930 0.058176 11.00000 0.05180 0.04681 = 0.05238 0.00378 0.00330 0.00005 C15 1 0.391804 0.437296 0.060862 11.00000 0.06822 0.04730 = 0.05426 -0.00124 0.00227 0.00304 AFIX 43 H15 2 0.411511 0.457683 0.148771 11.00000 -1.20000 AFIX 0 C16 1 0.324241 0.459771 -0.069212 11.00000 0.07324 0.04419 = 0.06694 0.00207 0.00021 0.00869 C17 1 0.296820 0.429398 -0.201616 11.00000 0.07000 0.05025 = 0.06079 0.00531 -0.00861 0.00675 C18 1 0.335858 0.375709 -0.202108 11.00000 0.06556 0.04988 = 0.05542 -0.00301 -0.00518 0.00219 C19 1 0.402127 0.353035 -0.071978 11.00000 0.06086 0.04316 = 0.05864 0.00068 -0.00035 0.00449 AFIX 43 H19 2 0.428038 0.317292 -0.071794 11.00000 -1.20000 AFIX 0 C20 1 0.288167 0.541574 0.057217 11.00000 0.12872 0.05365 = 0.09547 -0.00792 0.01219 0.02417 AFIX 137 H20A 2 0.248126 0.575979 0.035983 11.00000 -1.50000 H20B 2 0.377675 0.546469 0.098266 11.00000 -1.50000 H20C 2 0.244347 0.522776 0.129641 11.00000 -1.50000 AFIX 0 PART 1 C21A 1 0.290811 0.487273 -0.413879 21.00000 0.18872 0.07114 = 0.07796 0.02329 -0.02196 -0.01434 AFIX 137 H21A 2 0.325925 0.515995 -0.348707 21.00000 -1.50000 H21B 2 0.230597 0.501603 -0.495655 21.00000 -1.50000 H21C 2 0.359900 0.469237 -0.454649 21.00000 -1.50000 AFIX 0 PART 2 C21B 1 0.313666 0.474822 -0.423612 -21.00000 0.18872 0.07114 = 0.07796 0.02329 -0.02196 -0.01434 AFIX 137 H21D 2 0.370504 0.499367 -0.363453 -21.00000 -1.50000 H21E 2 0.264266 0.493885 -0.506053 -21.00000 -1.50000 H21F 2 0.364116 0.447335 -0.463584 -21.00000 -1.50000 AFIX 0 PART 0 C22 1 0.341274 0.294846 -0.341935 11.00000 0.14154 0.06035 = 0.07808 -0.01694 -0.02076 0.01921 AFIX 137 H22A 2 0.323669 0.282143 -0.444796 11.00000 -1.50000 H22B 2 0.293294 0.273779 -0.278310 11.00000 -1.50000 H22C 2 0.432395 0.291657 -0.306655 11.00000 -1.50000 AFIX 0 HKLF 4 REM 9_auto_a.res in P2(1)/c LIGHT YELLOW ROD REM wR2 = 0.1373, GooF = S = 1.053, Restrained GooF = 1.112 for all data REM R1 = 0.0454 for 4023 Fo > 4sig(Fo) and 0.0480 for all 4391 data REM 286 parameters refined using 14 restraints END WGHT 0.0768 0.4404 REM Instructions for potential hydrogen bonds HTAB C21A O2 REM Highest difference peak 0.312, deepest hole -0.265, 1-sigma level 0.034 Q1 1 1.0093 0.4400 1.2787 11.00000 0.05 0.31 Q2 1 1.1124 0.4168 1.2422 11.00000 0.05 0.24 Q3 1 0.2525 0.2892 -0.2905 11.00000 0.05 0.19 Q4 1 0.4662 0.3749 0.1234 11.00000 0.05 0.19 Q5 1 0.9790 0.3614 1.3614 11.00000 0.05 0.19 Q6 1 1.1399 0.3087 1.2594 11.00000 0.05 0.17 Q7 1 0.5994 0.3650 0.5168 11.00000 0.05 0.17 Q8 1 0.2662 0.2796 -0.4194 11.00000 0.05 0.17 Q9 1 0.8132 0.3145 0.8778 11.00000 0.05 0.15 Q10 1 0.9593 0.3707 1.0656 11.00000 0.05 0.15 ; _shelx_res_checksum 12855 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 S1 S 0.65665(5) 0.37451(2) 0.60050(5) 0.07292(19) Uani 1 1 d . . . . . O1 O 0.53307(11) 0.38893(4) 0.32221(12) 0.0584(3) Uani 1 1 d . . . . . O2 O 0.27984(17) 0.51133(5) -0.07883(17) 0.0881(5) Uani 1 1 d . . . . . O3 O 0.22596(15) 0.45039(6) -0.32929(16) 0.0855(4) Uani 1 1 d D . . . . O4 O 0.30342(15) 0.34963(5) -0.33607(15) 0.0803(4) Uani 1 1 d . . . . . N1 N 0.59366(16) 0.30476(5) 0.36516(16) 0.0636(4) Uani 1 1 d . . . . . N2 N 0.53099(14) 0.30946(5) 0.21414(15) 0.0600(3) Uani 1 1 d . . . . . C1 C 0.59207(16) 0.35213(6) 0.42158(18) 0.0558(4) Uani 1 1 d . . . . . C2 C 0.49776(14) 0.35875(6) 0.19434(16) 0.0494(3) Uani 1 1 d . . . . . C3 C 0.7459(2) 0.31393(7) 0.66696(19) 0.0673(4) Uani 1 1 d . . . . . H3A H 0.686023 0.284476 0.674222 0.081 Uiso 1 1 calc R U . . . H3B H 0.804805 0.303821 0.596183 0.081 Uiso 1 1 calc R U . . . C4 C 0.82072(17) 0.32568(6) 0.82063(18) 0.0584(4) Uani 1 1 d . . . . . C5 C 0.77040(16) 0.31192(6) 0.95153(19) 0.0572(4) Uani 1 1 d . . . . . H5 H 0.689902 0.295177 0.944311 0.069 Uiso 1 1 calc R U . . . C6 C 0.83845(16) 0.32278(7) 1.09270(18) 0.0583(4) Uani 1 1 d . . . . . H6 H 0.802074 0.313355 1.178939 0.070 Uiso 1 1 calc R U . . . C7 C 0.95850(16) 0.34713(8) 1.11045(19) 0.0628(4) Uani 1 1 d . . . . . C8 C 1.00824(19) 0.36046(10) 0.9784(2) 0.0830(6) Uani 1 1 d . . . . . H8 H 1.089394 0.376651 0.985843 0.100 Uiso 1 1 calc R U . . . C9 C 0.9408(2) 0.35038(10) 0.8363(2) 0.0792(6) Uani 1 1 d . . . . . H9 H 0.976482 0.360331 0.750001 0.095 Uiso 1 1 calc R U . . . C10 C 1.02980(19) 0.35920(11) 1.2694(2) 0.0870(6) Uani 1 1 d D . . . . C11A C 0.9536(4) 0.3992(2) 1.3473(5) 0.1239(15) Uani 0.699(3) 1 d D . P A 1 H11A H 0.865225 0.387334 1.341149 0.186 Uiso 0.699(3) 1 calc R U P A 1 H11B H 0.956089 0.433483 1.298461 0.186 Uiso 0.699(3) 1 calc R U P A 1 H11C H 0.990653 0.402293 1.452073 0.186 Uiso 0.699(3) 1 calc R U P A 1 C12A C 1.0243(4) 0.30595(19) 1.3759(4) 0.1105(13) Uani 0.699(3) 1 d D . P A 1 H12A H 0.935496 0.295739 1.377360 0.166 Uiso 0.699(3) 1 calc R U P A 1 H12B H 1.064139 0.313815 1.477567 0.166 Uiso 0.699(3) 1 calc R U P A 1 H12C H 1.069944 0.277012 1.335426 0.166 Uiso 0.699(3) 1 calc R U P A 1 C13A C 1.1714(3) 0.3708(2) 1.2779(5) 0.1075(16) Uani 0.699(3) 1 d D . P A 1 H13A H 1.211964 0.343139 1.225621 0.161 Uiso 0.699(3) 1 calc R U P A 1 H13B H 1.210110 0.371805 1.382495 0.161 Uiso 0.699(3) 1 calc R U P A 1 H13C H 1.183269 0.404853 1.231148 0.161 Uiso 0.699(3) 1 calc R U P A 1 C11B C 1.0476(10) 0.4246(3) 1.2561(10) 0.1239(15) Uani 0.301(3) 1 d D . P A 2 H11D H 1.120179 0.432209 1.203589 0.186 Uiso 0.301(3) 1 calc R U P A 2 H11E H 1.062505 0.439968 1.356171 0.186 Uiso 0.301(3) 1 calc R U P A 2 H11F H 0.970341 0.439848 1.200808 0.186 Uiso 0.301(3) 1 calc R U P A 2 C12B C 0.9660(9) 0.3486(5) 1.3952(8) 0.1105(13) Uani 0.301(3) 1 d D . P A 2 H12D H 0.892542 0.372013 1.393196 0.166 Uiso 0.301(3) 1 calc R U P A 2 H12E H 1.024558 0.354467 1.487132 0.166 Uiso 0.301(3) 1 calc R U P A 2 H12F H 0.937118 0.311908 1.391609 0.166 Uiso 0.301(3) 1 calc R U P A 2 C13B C 1.1655(7) 0.3394(4) 1.2657(13) 0.1075(16) Uani 0.301(3) 1 d D . P A 2 H13D H 1.193989 0.350073 1.171814 0.161 Uiso 0.301(3) 1 calc R U P A 2 H13E H 1.167103 0.300989 1.273512 0.161 Uiso 0.301(3) 1 calc R U P A 2 H13F H 1.222097 0.354599 1.349412 0.161 Uiso 0.301(3) 1 calc R U P A 2 C14 C 0.42968(14) 0.38393(6) 0.05818(17) 0.0507(3) Uani 1 1 d . . . . . C15 C 0.39180(16) 0.43730(6) 0.06086(19) 0.0572(4) Uani 1 1 d . . . . . H15 H 0.411511 0.457683 0.148771 0.069 Uiso 1 1 calc R U . . . C16 C 0.32424(17) 0.45977(6) -0.0692(2) 0.0623(4) Uani 1 1 d . . . . . C17 C 0.29682(17) 0.42940(7) -0.2016(2) 0.0620(4) Uani 1 1 d . . . . . C18 C 0.33586(16) 0.37571(6) -0.20211(19) 0.0582(4) Uani 1 1 d . . . . . C19 C 0.40213(15) 0.35304(6) -0.07198(18) 0.0550(4) Uani 1 1 d . . . . . H19 H 0.428038 0.317292 -0.071794 0.066 Uiso 1 1 calc R U . . . C20 C 0.2882(3) 0.54157(8) 0.0572(3) 0.0929(7) Uani 1 1 d . . . . . H20A H 0.248126 0.575979 0.035983 0.139 Uiso 1 1 calc R U . . . H20B H 0.377675 0.546469 0.098266 0.139 Uiso 1 1 calc R U . . . H20C H 0.244347 0.522776 0.129641 0.139 Uiso 1 1 calc R U . . . C21A C 0.2908(12) 0.4873(3) -0.4139(16) 0.116(2) Uani 0.699(3) 1 d D . P A 1 H21A H 0.325925 0.515995 -0.348707 0.175 Uiso 0.699(3) 1 calc R U P A 1 H21B H 0.230597 0.501603 -0.495655 0.175 Uiso 0.699(3) 1 calc R U P A 1 H21C H 0.359900 0.469237 -0.454649 0.175 Uiso 0.699(3) 1 calc R U P A 1 C21B C 0.314(3) 0.4748(10) -0.424(4) 0.116(2) Uani 0.301(3) 1 d D . P A 2 H21D H 0.370504 0.499367 -0.363453 0.175 Uiso 0.301(3) 1 calc R U P A 2 H21E H 0.264266 0.493885 -0.506053 0.175 Uiso 0.301(3) 1 calc R U P A 2 H21F H 0.364116 0.447335 -0.463584 0.175 Uiso 0.301(3) 1 calc R U P A 2 C22 C 0.3413(3) 0.29485(8) -0.3419(3) 0.0967(8) Uani 1 1 d . . . . . H22A H 0.323669 0.282143 -0.444796 0.145 Uiso 1 1 calc R U . . . H22B H 0.293294 0.273779 -0.278310 0.145 Uiso 1 1 calc R U . . . H22C H 0.432395 0.291657 -0.306655 0.145 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 0.1086(4) 0.0541(3) 0.0506(3) -0.00483(16) -0.0084(2) 0.0137(2) O1 0.0781(7) 0.0443(5) 0.0496(6) 0.0000(4) -0.0021(5) 0.0064(5) O2 0.1288(12) 0.0501(7) 0.0777(9) -0.0017(6) -0.0128(8) 0.0289(7) O3 0.1086(10) 0.0644(8) 0.0727(8) 0.0084(6) -0.0263(7) 0.0156(7) O4 0.1093(10) 0.0582(7) 0.0632(7) -0.0097(5) -0.0241(7) 0.0164(7) N1 0.0870(9) 0.0483(7) 0.0518(7) 0.0026(5) -0.0039(7) 0.0081(6) N2 0.0771(8) 0.0468(7) 0.0526(7) 0.0010(5) -0.0038(6) 0.0044(6) C1 0.0698(9) 0.0490(8) 0.0472(8) 0.0043(6) 0.0027(7) 0.0048(7) C2 0.0538(7) 0.0448(7) 0.0491(8) 0.0002(6) 0.0054(6) -0.0008(6) C3 0.0902(12) 0.0562(9) 0.0517(9) -0.0020(7) -0.0040(8) 0.0109(8) C4 0.0719(10) 0.0517(8) 0.0497(8) -0.0004(6) 0.0011(7) 0.0064(7) C5 0.0614(8) 0.0497(8) 0.0582(9) 0.0052(6) -0.0002(7) -0.0051(6) C6 0.0598(8) 0.0649(9) 0.0498(8) 0.0066(7) 0.0058(7) -0.0045(7) C7 0.0538(8) 0.0799(11) 0.0543(9) -0.0035(8) 0.0058(7) -0.0031(8) C8 0.0604(10) 0.1236(17) 0.0666(11) -0.0049(11) 0.0142(8) -0.0231(11) C9 0.0779(12) 0.1069(16) 0.0557(10) -0.0001(10) 0.0193(9) -0.0115(11) C10 0.0640(11) 0.1290(18) 0.0647(12) -0.0172(12) -0.0033(9) -0.0097(11) C11A 0.127(3) 0.164(4) 0.075(2) -0.045(2) -0.0058(19) 0.002(3) C12A 0.109(3) 0.152(4) 0.0638(17) 0.028(2) -0.0126(17) -0.022(2) C13A 0.0742(15) 0.167(5) 0.0744(18) 0.004(3) -0.0123(13) -0.046(3) C11B 0.127(3) 0.164(4) 0.075(2) -0.045(2) -0.0058(19) 0.002(3) C12B 0.109(3) 0.152(4) 0.0638(17) 0.028(2) -0.0126(17) -0.022(2) C13B 0.0742(15) 0.167(5) 0.0744(18) 0.004(3) -0.0123(13) -0.046(3) C14 0.0518(7) 0.0468(7) 0.0524(8) 0.0038(6) 0.0033(6) 0.0001(6) C15 0.0682(9) 0.0473(8) 0.0543(8) -0.0012(6) 0.0023(7) 0.0030(7) C16 0.0732(10) 0.0442(8) 0.0669(10) 0.0021(7) 0.0002(8) 0.0087(7) C17 0.0700(10) 0.0502(8) 0.0608(9) 0.0053(7) -0.0086(7) 0.0068(7) C18 0.0656(9) 0.0499(8) 0.0554(9) -0.0030(6) -0.0052(7) 0.0022(6) C19 0.0609(8) 0.0432(7) 0.0586(9) 0.0007(6) -0.0003(7) 0.0045(6) C20 0.1287(19) 0.0537(10) 0.0955(15) -0.0079(10) 0.0122(14) 0.0242(11) C21A 0.189(5) 0.071(5) 0.078(2) 0.023(4) -0.022(3) -0.014(4) C21B 0.189(5) 0.071(5) 0.078(2) 0.023(4) -0.022(3) -0.014(4) C22 0.142(2) 0.0604(11) 0.0781(14) -0.0169(10) -0.0208(13) 0.0192(12) 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 C1 S1 C3 98.42(8) . . ? C1 O1 C2 102.34(12) . . ? C16 O2 C20 117.85(15) . . ? C17 O3 C21A 116.5(7) . . ? C17 O3 C21B 109.1(17) . . ? C18 O4 C22 117.04(14) . . ? C1 N1 N2 105.39(12) . . ? C2 N2 N1 106.87(13) . . ? N1 C1 O1 113.31(14) . . ? N1 C1 S1 129.10(12) . . ? O1 C1 S1 117.56(11) . . ? N2 C2 O1 112.08(13) . . ? N2 C2 C14 128.17(14) . . ? O1 C2 C14 119.75(13) . . ? C4 C3 S1 108.00(12) . . ? C4 C3 H3A 110.1 . . ? S1 C3 H3A 110.1 . . ? C4 C3 H3B 110.1 . . ? S1 C3 H3B 110.1 . . ? H3A C3 H3B 108.4 . . ? C5 C4 C9 117.90(16) . . ? C5 C4 C3 120.39(16) . . ? C9 C4 C3 121.71(16) . . ? C6 C5 C4 120.61(15) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C7 C6 C5 122.28(15) . . ? C7 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? C6 C7 C8 116.57(16) . . ? C6 C7 C10 120.55(16) . . ? C8 C7 C10 122.87(16) . . ? C9 C8 C7 121.87(18) . . ? C9 C8 H8 119.1 . . ? C7 C8 H8 119.1 . . ? C8 C9 C4 120.76(17) . . ? C8 C9 H9 119.6 . . ? C4 C9 H9 119.6 . . ? C12B C10 C13B 120.4(6) . . ? C13A C10 C11A 115.4(3) . . ? C12B C10 C7 118.4(4) . . ? C13A C10 C7 115.7(2) . . ? C13B C10 C7 104.7(4) . . ? C11A C10 C7 109.6(2) . . ? C13A C10 C12A 103.9(3) . . ? C11A C10 C12A 102.0(3) . . ? C7 C10 C12A 108.8(2) . . ? C12B C10 C11B 108.3(6) . . ? C13B C10 C11B 102.0(5) . . ? C7 C10 C11B 100.0(3) . . ? C10 C11A H11A 109.5 . . ? C10 C11A H11B 109.5 . . ? H11A C11A H11B 109.5 . . ? C10 C11A H11C 109.5 . . ? H11A C11A H11C 109.5 . . ? H11B C11A H11C 109.5 . . ? C10 C12A H12A 109.5 . . ? C10 C12A H12B 109.5 . . ? H12A C12A H12B 109.5 . . ? C10 C12A H12C 109.5 . . ? H12A C12A H12C 109.5 . . ? H12B C12A H12C 109.5 . . ? C10 C13A H13A 109.5 . . ? C10 C13A H13B 109.5 . . ? H13A C13A H13B 109.5 . . ? C10 C13A H13C 109.5 . . ? H13A C13A H13C 109.5 . . ? H13B C13A H13C 109.5 . . ? C10 C11B H11D 109.5 . . ? C10 C11B H11E 109.5 . . ? H11D C11B H11E 109.5 . . ? C10 C11B H11F 109.5 . . ? H11D C11B H11F 109.5 . . ? H11E C11B H11F 109.5 . . ? C10 C12B H12D 109.5 . . ? C10 C12B H12E 109.5 . . ? H12D C12B H12E 109.5 . . ? C10 C12B H12F 109.5 . . ? H12D C12B H12F 109.5 . . ? H12E C12B H12F 109.5 . . ? C10 C13B H13D 109.5 . . ? C10 C13B H13E 109.5 . . ? H13D C13B H13E 109.5 . . ? C10 C13B H13F 109.5 . . ? H13D C13B H13F 109.5 . . ? H13E C13B H13F 109.5 . . ? C19 C14 C15 121.33(14) . . ? C19 C14 C2 118.32(13) . . ? C15 C14 C2 120.34(14) . . ? C16 C15 C14 119.05(15) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? O2 C16 C15 124.17(16) . . ? O2 C16 C17 115.47(15) . . ? C15 C16 C17 120.36(15) . . ? O3 C17 C16 121.04(15) . . ? O3 C17 C18 119.12(15) . . ? C16 C17 C18 119.74(15) . . ? O4 C18 C19 124.94(14) . . ? O4 C18 C17 115.06(14) . . ? C19 C18 C17 120.00(15) . . ? C18 C19 C14 119.51(14) . . ? C18 C19 H19 120.2 . . ? C14 C19 H19 120.2 . . ? O2 C20 H20A 109.5 . . ? O2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O3 C21A H21A 109.5 . . ? O3 C21A H21B 109.5 . . ? H21A C21A H21B 109.5 . . ? O3 C21A H21C 109.5 . . ? H21A C21A H21C 109.5 . . ? H21B C21A H21C 109.5 . . ? O3 C21B H21D 109.5 . . ? O3 C21B H21E 109.5 . . ? H21D C21B H21E 109.5 . . ? O3 C21B H21F 109.5 . . ? H21D C21B H21F 109.5 . . ? H21E C21B H21F 109.5 . . ? O4 C22 H22A 109.5 . . ? O4 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O4 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? 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 S1 C1 1.7295(16) . ? S1 C3 1.8262(18) . ? O1 C1 1.3586(18) . ? O1 C2 1.3690(18) . ? O2 C16 1.3634(19) . ? O2 C20 1.416(3) . ? O3 C17 1.368(2) . ? O3 C21A 1.415(5) . ? O3 C21B 1.455(10) . ? O4 C18 1.356(2) . ? O4 C22 1.423(2) . ? N1 C1 1.283(2) . ? N1 N2 1.4127(19) . ? N2 C2 1.281(2) . ? C2 C14 1.456(2) . ? C3 C4 1.504(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.382(2) . ? C4 C9 1.382(3) . ? C5 C6 1.379(2) . ? C5 H5 0.9300 . ? C6 C7 1.378(2) . ? C6 H6 0.9300 . ? C7 C8 1.385(3) . ? C7 C10 1.531(2) . ? C8 C9 1.380(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C12B 1.402(7) . ? C10 C13A 1.493(4) . ? C10 C13B 1.500(8) . ? C10 C11A 1.500(4) . ? C10 C12A 1.635(4) . ? C10 C11B 1.646(7) . ? C11A H11A 0.9600 . ? C11A H11B 0.9600 . ? C11A H11C 0.9600 . ? C12A H12A 0.9600 . ? C12A H12B 0.9600 . ? C12A H12C 0.9600 . ? C13A H13A 0.9600 . ? C13A H13B 0.9600 . ? C13A H13C 0.9600 . ? C11B H11D 0.9600 . ? C11B H11E 0.9600 . ? C11B H11F 0.9600 . ? C12B H12D 0.9600 . ? C12B H12E 0.9600 . ? C12B H12F 0.9600 . ? C13B H13D 0.9600 . ? C13B H13E 0.9600 . ? C13B H13F 0.9600 . ? C14 C19 1.385(2) . ? C14 C15 1.387(2) . ? C15 C16 1.385(2) . ? C15 H15 0.9300 . ? C16 C17 1.394(2) . ? C17 C18 1.398(2) . ? C18 C19 1.382(2) . ? C19 H19 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21A H21A 0.9600 . ? C21A H21B 0.9600 . ? C21A H21C 0.9600 . ? C21B H21D 0.9600 . ? C21B H21E 0.9600 . ? C21B H21F 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 _geom_hbond_publ_flag C21A^a H21A^a O2 0.96 2.51 3.052(13) 115.7 . 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 C2 -0.12(18) . . . . ? N2 N1 C1 O1 0.3(2) . . . . ? N2 N1 C1 S1 -178.11(13) . . . . ? C2 O1 C1 N1 -0.31(19) . . . . ? C2 O1 C1 S1 178.28(11) . . . . ? C3 S1 C1 N1 8.42(19) . . . . ? C3 S1 C1 O1 -169.91(13) . . . . ? N1 N2 C2 O1 -0.08(18) . . . . ? N1 N2 C2 C14 -179.61(15) . . . . ? C1 O1 C2 N2 0.23(17) . . . . ? C1 O1 C2 C14 179.80(13) . . . . ? C1 S1 C3 C4 175.56(13) . . . . ? S1 C3 C4 C5 95.98(17) . . . . ? S1 C3 C4 C9 -83.9(2) . . . . ? C9 C4 C5 C6 0.1(3) . . . . ? C3 C4 C5 C6 -179.76(15) . . . . ? C4 C5 C6 C7 -0.5(3) . . . . ? C5 C6 C7 C8 0.1(3) . . . . ? C5 C6 C7 C10 179.09(18) . . . . ? C6 C7 C8 C9 0.6(3) . . . . ? C10 C7 C8 C9 -178.4(2) . . . . ? C7 C8 C9 C4 -0.9(4) . . . . ? C5 C4 C9 C8 0.5(3) . . . . ? C3 C4 C9 C8 -179.5(2) . . . . ? C6 C7 C10 C12B -4.7(7) . . . . ? C8 C7 C10 C12B 174.2(6) . . . . ? C6 C7 C10 C13A 163.3(3) . . . . ? C8 C7 C10 C13A -17.8(4) . . . . ? C6 C7 C10 C13B 132.8(5) . . . . ? C8 C7 C10 C13B -48.3(5) . . . . ? C6 C7 C10 C11A -64.1(3) . . . . ? C8 C7 C10 C11A 114.8(3) . . . . ? C6 C7 C10 C12A 46.7(3) . . . . ? C8 C7 C10 C12A -134.4(3) . . . . ? C6 C7 C10 C11B -121.9(4) . . . . ? C8 C7 C10 C11B 57.0(5) . . . . ? N2 C2 C14 C19 -4.3(2) . . . . ? O1 C2 C14 C19 176.23(13) . . . . ? N2 C2 C14 C15 174.60(16) . . . . ? O1 C2 C14 C15 -4.9(2) . . . . ? C19 C14 C15 C16 0.5(2) . . . . ? C2 C14 C15 C16 -178.33(15) . . . . ? C20 O2 C16 C15 -8.7(3) . . . . ? C20 O2 C16 C17 171.0(2) . . . . ? C14 C15 C16 O2 178.55(17) . . . . ? C14 C15 C16 C17 -1.1(3) . . . . ? C21A O3 C17 C16 75.5(5) . . . . ? C21B O3 C17 C16 91.3(13) . . . . ? C21A O3 C17 C18 -108.0(5) . . . . ? C21B O3 C17 C18 -92.3(13) . . . . ? O2 C16 C17 O3 -2.2(3) . . . . ? C15 C16 C17 O3 177.51(17) . . . . ? O2 C16 C17 C18 -178.61(17) . . . . ? C15 C16 C17 C18 1.1(3) . . . . ? C22 O4 C18 C19 -0.2(3) . . . . ? C22 O4 C18 C17 180.0(2) . . . . ? O3 C17 C18 O4 2.9(3) . . . . ? C16 C17 C18 O4 179.42(17) . . . . ? O3 C17 C18 C19 -176.91(16) . . . . ? C16 C17 C18 C19 -0.4(3) . . . . ? O4 C18 C19 C14 179.97(16) . . . . ? C17 C18 C19 C14 -0.2(3) . . . . ? C15 C14 C19 C18 0.1(2) . . . . ? C2 C14 C19 C18 179.01(14) . . . . ?