#------------------------------------------------------------------------------ #$Date: 2026-06-25 00:07:02 +0100 (Thu, 25 Jun 2026) $ #$Revision: 306639 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/74/1577431.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_1577431 loop_ _publ_author_name 'Schiele, Stefanie' 'Paschke, Ann-Sophie K.' 'Romiti, Giorgia' 'Morandi, Bill' _publ_section_title ; Direct access to 2-imidazolines from unactivated alkenes ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D6SC03337G _journal_year 2026 _chemical_formula_moiety 'C7 H7 O3 S, C6 H11 N2' _chemical_formula_sum 'C13 H18 N2 O3 S' _chemical_formula_weight 282.35 _chemical_name_systematic '2,5,6,7-Tetrahydro-3H-pyrrolo[1,2-a]imidazole (TsOH salt)' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2025-11-10 _audit_creation_method ; Olex2 1.5 (compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314) ; _audit_update_record ; 2026-02-05 deposited with the CCDC. 2026-06-09 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 107.7550(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.73180(10) _cell_length_b 20.8161(2) _cell_length_c 8.62370(10) _cell_measurement_reflns_used 13211 _cell_measurement_temperature 100.0(1) _cell_measurement_theta_max 73.8530 _cell_measurement_theta_min 4.2310 _cell_volume 1321.84(3) _computing_cell_refinement 'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)' _computing_data_collection 'CrysAlisPro system (CCD 44.119a 64-bit (release 12-08-2025))' _computing_data_reduction 'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2019/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.0(1) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type 'HyPix-Arc 150' _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.967 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w 36.00 90.00 0.50 0.05 -- 70.80-125.00 150.00 108 2 \w 22.00 47.00 0.50 0.05 -- 67.97-125.00 30.00 50 3 \w 26.00 77.00 0.50 0.05 -- 70.80-125.00 -30.00 102 4 \w 44.00 79.00 0.50 0.07 -- 77.82-125.00 0.00 70 5 \w 71.00 97.00 0.50 0.07 -- 77.82-125.00 60.00 52 6 \w 73.00 98.00 0.50 0.07 -- 77.82-125.00 30.00 50 7 \w 25.00 50.00 0.50 0.05 -- 70.80-125.00 -90.00 50 8 \w 21.00 46.00 0.50 0.05 -- 67.97-125.00-150.00 50 9 \w 34.00 63.00 0.50 0.07 -- 77.82-125.00-180.00 58 10 \w 70.00 97.00 0.50 0.07 -- 77.82-125.00-180.00 54 11 \w 73.00 98.00 0.50 0.07 -- 77.82-125.00-150.00 50 12 \w 45.00 70.00 0.50 0.07 -- 77.82-125.00-150.00 50 13 \w 73.00 98.00 0.50 0.07 -- 77.82-125.00-120.00 50 14 \w 43.00 68.00 0.50 0.07 -- 77.82-125.00-120.00 50 15 \w 62.00 98.00 0.50 0.07 -- 77.82-125.00 -30.00 72 16 \w 59.00 85.00 0.50 0.05 -- 67.97-124.00 54.00 52 17 \w 31.00 98.00 0.50 0.07 -- 77.82-124.00 54.00 134 18 \w 39.00 65.00 0.50 0.07 -- 77.82-125.00 120.00 52 19 \w 73.00 98.00 0.50 0.07 -- 77.82-125.00 120.00 50 20 \w 38.00 81.00 0.50 0.07 -- 77.82 -95.00 60.00 86 21 \w 44.00 69.00 0.50 0.05 -- 70.80-124.00 54.00 50 22 \w 21.00 46.00 0.50 0.05 -- 67.97-124.00 54.00 50 23 \w 50.00 76.00 0.50 0.07 -- 77.82 -95.00 120.00 52 24 \w 46.00 72.00 0.50 0.05 -- 67.97 -95.00-150.00 52 25 \w 52.00 77.00 0.50 0.07 -- 77.82 -95.00-180.00 50 26 \w -122.00 -97.00 0.50 0.07 -- -75.17 -36.00 155.98 50 27 \w -112.00 -87.00 0.50 0.05 -- -70.00 -66.00 152.57 50 28 \w -112.00 -87.00 0.50 0.05 -- -70.00 -66.00 113.16 50 29 \w -117.00 -92.00 0.50 0.07 -- -75.17 -67.00 82.54 50 30 \w -112.00 -87.00 0.50 0.05 -- -70.00 -67.00 79.70 50 31 \w -115.00 -90.00 0.50 0.05 -- -70.00 -56.00 166.01 50 32 \w -115.00 -90.00 0.50 0.05 -- -70.00 -56.00 23.28 50 33 \w -121.00 -96.00 0.50 0.07 -- -75.17 -56.00 88.99 50 34 \w -108.00 -83.00 0.50 0.05 -- -70.00 -63.00 -32.78 50 35 \w -119.00 -94.00 0.50 0.07 -- -75.17 -56.00 -89.62 50 36 \w -115.00 -89.00 0.50 0.05 -- -70.00 -56.00-148.37 52 37 \w -121.00 -95.00 0.50 0.07 -- -75.17 -55.00-167.40 52 38 \w -112.00 -86.00 0.50 0.05 -- -70.00 -67.00-103.16 52 39 \w -118.00 -93.00 0.50 0.05 -- -74.00 -62.00 -46.79 50 40 \w -121.00 -96.00 0.50 0.07 -- -75.17 -54.00 -43.22 50 41 \w -107.00 -82.00 0.50 0.05 -- -62.00 -54.00 -80.18 50 42 \w -106.00 -80.00 0.50 0.05 -- -62.00 -54.00 -27.94 52 43 \w -117.00 -92.00 0.50 0.07 -- -75.17 -55.00 119.45 50 44 \w -120.00 -95.00 0.50 0.07 -- -75.17 -55.00 130.23 50 45 \w -120.00 -95.00 0.50 0.05 -- -72.64 -50.00 166.07 50 46 \w -121.00 -96.00 0.50 0.07 -- -75.17 -55.00 160.58 50 47 \w -120.00 -95.00 0.50 0.05 -- -72.64 -50.00 49.27 50 48 \w -121.00 -96.00 0.50 0.07 -- -75.17 -49.00 18.74 50 49 \w -120.00 -95.00 0.50 0.05 -- -72.64 -50.00 -82.34 50 50 \w -119.00 -94.00 0.50 0.05 -- -72.64 -51.00-155.43 50 51 \w -120.00 -95.00 0.50 0.05 -- -72.64 -50.00-133.36 50 52 \w -121.00 -96.00 0.50 0.05 -- -72.64 -41.00 -44.40 50 53 \w -122.00 -97.00 0.50 0.07 -- -75.17 -39.00 -90.93 50 54 \w -121.00 -96.00 0.50 0.05 -- -72.64 -42.00 -31.17 50 55 \w -120.00 -95.00 0.50 0.05 -- -72.64 -39.00 18.00 50 56 \w -117.00 -92.00 0.50 0.05 -- -70.00 -48.00 126.71 50 57 \w -123.00 -98.00 0.50 0.07 -- -75.17 -37.00 94.21 50 58 \w -122.00 -97.00 0.50 0.05 -- -72.64 -40.00 82.28 50 59 \w -123.00 -97.00 0.50 0.07 -- -75.17 -37.00-132.72 52 60 \w -123.00 -98.00 0.50 0.07 -- -75.17 -38.00-155.11 50 61 \w -62.00 -21.00 0.50 0.05 -- -66.23 125.00 -90.00 82 62 \w -94.00 -41.00 0.50 0.07 -- -75.17 122.00-148.64 106 63 \w -88.00 -26.00 0.50 0.05 -- -69.37 125.00 30.00 124 64 \w -48.00 -23.00 0.50 0.05 -- -66.23 124.00 133.00 50 65 \w -72.00 -27.00 0.50 0.05 -- -69.37 124.00 133.00 90 66 \w -91.00 -65.00 0.50 0.07 -- -75.17 122.00 161.29 52 67 \w -68.00 -41.00 0.50 0.05 -- -72.64 91.00 149.89 54 68 \w -87.00 -53.00 0.50 0.07 -- -75.17 110.00 -73.97 68 69 \w -87.00 -62.00 0.50 0.07 -- -75.17 119.00-141.20 50 70 \w -53.00 -28.00 0.50 0.07 -- -75.17 119.00-141.20 50 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy R, HyPix-Arc 150' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.1850698000 _diffrn_orient_matrix_UB_12 0.0049181000 _diffrn_orient_matrix_UB_13 -0.1331718000 _diffrn_orient_matrix_UB_21 -0.0201802000 _diffrn_orient_matrix_UB_22 -0.0736206000 _diffrn_orient_matrix_UB_23 0.0019713000 _diffrn_orient_matrix_UB_31 -0.0955573000 _diffrn_orient_matrix_UB_32 0.0060699000 _diffrn_orient_matrix_UB_33 0.1319975000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_unetI/netI 0.0126 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.967 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 22968 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.967 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 74.446 _diffrn_reflns_theta_min 4.248 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'PhotonJet R (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.242 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.678 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.43.144a (Rigaku Oxford Diffraction, 2024) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.419 _exptl_crystal_description block _exptl_crystal_F_000 600 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM, methanol' _exptl_crystal_size_max 0.154 _exptl_crystal_size_mid 0.149 _exptl_crystal_size_min 0.047 _refine_diff_density_max 0.244 _refine_diff_density_min -0.401 _refine_diff_density_rms 0.048 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 176 _refine_ls_number_reflns 2608 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.074 _refine_ls_R_factor_all 0.0323 _refine_ls_R_factor_gt 0.0302 _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^)+(0.0453P)^2^+0.4723P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0827 _refine_ls_wR_factor_ref 0.0841 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2433 _reflns_number_total 2608 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc03337g2.cif _cod_data_source_block bm091125_1_1 _cod_database_code 1577431 _shelx_shelxl_version_number 2019/3 _chemical_oxdiff_formula C13H18N2O3S _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_max 0.896 _shelx_estimated_absorpt_t_min 0.730 _diffrn_oxdiff_ac3_digest_hkl 41ef7dd55143f4685e274541b1b185802780f4 _diffrn_oxdiff_digest_hkl ; 4364e992e98ee72e895abc4d79f58ee9506de7 ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances N1-H1 0.93 with sigma of 0.02 3.a Secondary CH2 refined with riding coordinates: C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B) 3.b Aromatic/amide H refined with riding coordinates: C8(H8), C9(H9), C12(H12), C13(H13) 3.c Idealised Me refined as rotating group: C11(H11A,H11B,H11C) ; _shelx_res_file ; TITL bm091125_1_1_a.res in P2(1)/n bm091125_1_1.res created by SHELXL-2019/3 at 13:47:13 on 10-Nov-2025 REM Old TITL bm091125_1_1 in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.090, Rweak 0.005, Alpha 0.025 REM 0.438 for 87 systematic absences, Orientation as input REM Formula found by SHELXT: C13 N2 O3 S CELL 1.54184 7.7318 20.8161 8.6237 90 107.755 90 ZERR 4 0.0001 0.0002 0.0001 0 0.001 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O S UNIT 52 72 8 12 4 DFIX 0.93 N1 H1 L.S. 9 PLAN 10 SIZE 0.05 0.15 0.15 TEMP -173 CONF BOND list 4 fmap 2 ACTA MORE -1 BOND $H REM REM REM WGHT 0.045300 0.472300 FVAR 0.42501 S1 5 0.246995 0.619539 0.351231 11.00000 0.02088 0.01868 = 0.01866 -0.00043 0.00464 -0.00007 O1 4 0.158943 0.681805 0.323341 11.00000 0.03857 0.01944 = 0.02866 0.00126 0.00140 0.00441 O2 4 0.116374 0.566795 0.326038 11.00000 0.02581 0.02215 = 0.02767 -0.00207 0.00319 -0.00493 O3 4 0.377806 0.610278 0.263780 11.00000 0.02538 0.05307 = 0.02066 -0.00110 0.00848 0.00039 C7 1 0.372150 0.616459 0.561416 11.00000 0.01967 0.01984 = 0.01887 -0.00073 0.00699 -0.00076 C8 1 0.413837 0.557325 0.639317 11.00000 0.02764 0.01867 = 0.02385 -0.00168 0.00666 -0.00256 AFIX 43 H8 2 0.369582 0.518814 0.581760 11.00000 -1.20000 AFIX 0 C9 1 0.520217 0.554687 0.801305 11.00000 0.02736 0.02214 = 0.02399 0.00307 0.00676 0.00053 AFIX 43 H9 2 0.548500 0.514138 0.853446 11.00000 -1.20000 AFIX 0 C10 1 0.586229 0.610545 0.888733 11.00000 0.01930 0.02805 = 0.01948 -0.00044 0.00739 0.00039 C11 1 0.693349 0.608054 1.067033 11.00000 0.02741 0.03618 = 0.02127 -0.00014 0.00499 0.00075 AFIX 137 H11A 2 0.611714 0.615411 1.132690 11.00000 -1.50000 H11B 2 0.787366 0.641369 1.091181 11.00000 -1.50000 H11C 2 0.750549 0.565762 1.093046 11.00000 -1.50000 AFIX 0 C12 1 0.545627 0.669379 0.808248 11.00000 0.02566 0.02245 = 0.02308 -0.00526 0.00899 -0.00260 AFIX 43 H12 2 0.591916 0.707851 0.865059 11.00000 -1.20000 AFIX 0 C13 1 0.438550 0.672701 0.646267 11.00000 0.02632 0.01728 = 0.02252 -0.00076 0.00893 0.00014 AFIX 43 H13 2 0.410818 0.713191 0.593714 11.00000 -1.20000 AFIX 0 N1 3 0.022478 0.442194 0.242580 11.00000 0.02808 0.01796 = 0.02435 -0.00071 0.00506 -0.00211 H1 2 0.060852 0.482982 0.269928 11.00000 -1.20000 N2 3 0.010579 0.337409 0.257876 11.00000 0.02831 0.01906 = 0.01945 0.00089 0.00337 -0.00139 C1 1 -0.094188 0.423271 0.079493 11.00000 0.03692 0.02183 = 0.02005 0.00061 0.00493 0.00028 AFIX 23 H1A 2 -0.038144 0.435316 -0.005402 11.00000 -1.20000 H1B 2 -0.215378 0.443614 0.054081 11.00000 -1.20000 AFIX 0 C2 1 -0.108049 0.349385 0.092202 11.00000 0.02771 0.02248 = 0.01854 0.00043 0.00371 -0.00158 AFIX 23 H2A 2 -0.234342 0.335669 0.078976 11.00000 -1.20000 H2B 2 -0.063324 0.327230 0.010300 11.00000 -1.20000 AFIX 0 C3 1 0.056829 0.280239 0.359202 11.00000 0.03452 0.02054 = 0.02348 0.00218 0.00563 0.00211 AFIX 23 H3A 2 0.115245 0.247402 0.308778 11.00000 -1.20000 H3B 2 -0.052009 0.261374 0.379131 11.00000 -1.20000 AFIX 0 C4 1 0.190749 0.306572 0.518033 11.00000 0.02673 0.02750 = 0.02293 0.00439 0.00495 -0.00117 AFIX 23 H4A 2 0.154180 0.292572 0.613210 11.00000 -1.20000 H4B 2 0.314996 0.290573 0.531209 11.00000 -1.20000 AFIX 0 C5 1 0.185400 0.380543 0.504752 11.00000 0.02164 0.02655 = 0.02155 -0.00297 0.00395 0.00172 AFIX 23 H5A 2 0.127122 0.399843 0.581189 11.00000 -1.20000 H5B 2 0.308948 0.398626 0.526496 11.00000 -1.20000 AFIX 0 C6 1 0.074756 0.391109 0.333292 11.00000 0.01854 0.02191 = 0.02109 -0.00112 0.00784 -0.00023 HKLF 4 REM bm091125_1_1_a.res in P2(1)/n REM wR2 = 0.0841, GooF = S = 1.074, Restrained GooF = 1.074 for all data REM R1 = 0.0302 for 2433 Fo > 4sig(Fo) and 0.0323 for all 2608 data REM 176 parameters refined using 1 restraints END WGHT 0.0453 0.4723 REM Highest difference peak 0.244, deepest hole -0.401, 1-sigma level 0.048 Q1 1 0.3134 0.6181 0.4732 11.00000 0.05 0.24 Q2 1 -0.1000 0.3867 0.0854 11.00000 0.05 0.22 Q3 1 0.1382 0.3892 0.4229 11.00000 0.05 0.21 Q4 1 0.1915 0.3445 0.5127 11.00000 0.05 0.18 Q5 1 0.6418 0.6102 0.9803 11.00000 0.05 0.17 Q6 1 0.3998 0.6442 0.5999 11.00000 0.05 0.17 Q7 1 0.1261 0.2918 0.4401 11.00000 0.05 0.17 Q8 1 0.3940 0.5881 0.5994 11.00000 0.05 0.16 Q9 1 0.5498 0.5855 0.8417 11.00000 0.05 0.15 Q10 1 0.4433 0.5589 0.7298 11.00000 0.05 0.15 ; _shelx_res_checksum 19971 _olex2_date_sample_data_collection 2025-11-07 _olex2_date_sample_submission 2025-11-06 _olex2_submission_original_sample_id bm091125_1_1 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling - Detector area scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.240 _oxdiff_exptl_absorpt_empirical_full_min 0.868 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' 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 0.24699(4) 0.61954(2) 0.35123(4) 0.01972(11) Uani 1 1 d . . . . . O1 O 0.15894(14) 0.68180(5) 0.32334(12) 0.0309(2) Uani 1 1 d . . . . . O2 O 0.11637(13) 0.56680(4) 0.32604(12) 0.0263(2) Uani 1 1 d . . . . . O3 O 0.37781(14) 0.61028(5) 0.26378(12) 0.0327(3) Uani 1 1 d . . . . . C7 C 0.37215(18) 0.61646(6) 0.56142(16) 0.0192(3) Uani 1 1 d . . . . . C8 C 0.41384(18) 0.55732(6) 0.63932(16) 0.0237(3) Uani 1 1 d . . . . . H8 H 0.369582 0.518814 0.581760 0.028 Uiso 1 1 calc R U . . . C9 C 0.52022(19) 0.55469(7) 0.80131(16) 0.0247(3) Uani 1 1 d . . . . . H9 H 0.548500 0.514138 0.853446 0.030 Uiso 1 1 calc R U . . . C10 C 0.58623(18) 0.61054(6) 0.88873(16) 0.0219(3) Uani 1 1 d . . . . . C11 C 0.6933(2) 0.60805(7) 1.06703(17) 0.0288(3) Uani 1 1 d . . . . . H11A H 0.611714 0.615411 1.132690 0.043 Uiso 1 1 calc R U . . . H11B H 0.787366 0.641369 1.091181 0.043 Uiso 1 1 calc R U . . . H11C H 0.750549 0.565762 1.093046 0.043 Uiso 1 1 calc R U . . . C12 C 0.54563(18) 0.66938(6) 0.80825(16) 0.0234(3) Uani 1 1 d . . . . . H12 H 0.591916 0.707851 0.865059 0.028 Uiso 1 1 calc R U . . . C13 C 0.43855(18) 0.67270(6) 0.64627(16) 0.0217(3) Uani 1 1 d . . . . . H13 H 0.410818 0.713191 0.593714 0.026 Uiso 1 1 calc R U . . . N1 N 0.02248(16) 0.44219(5) 0.24258(14) 0.0241(3) Uani 1 1 d D . . . . H1 H 0.061(2) 0.4830(7) 0.2699(19) 0.029 Uiso 1 1 d D U . . . N2 N 0.01058(16) 0.33741(5) 0.25788(13) 0.0231(2) Uani 1 1 d . . . . . C1 C -0.0942(2) 0.42327(6) 0.07949(16) 0.0271(3) Uani 1 1 d . . . . . H1A H -0.038144 0.435316 -0.005402 0.033 Uiso 1 1 calc R U . . . H1B H -0.215378 0.443614 0.054081 0.033 Uiso 1 1 calc R U . . . C2 C -0.10805(19) 0.34938(6) 0.09220(16) 0.0237(3) Uani 1 1 d . . . . . H2A H -0.234342 0.335669 0.078976 0.028 Uiso 1 1 calc R U . . . H2B H -0.063324 0.327230 0.010300 0.028 Uiso 1 1 calc R U . . . C3 C 0.0568(2) 0.28024(6) 0.35920(16) 0.0269(3) Uani 1 1 d . . . . . H3A H 0.115245 0.247402 0.308778 0.032 Uiso 1 1 calc R U . . . H3B H -0.052009 0.261374 0.379131 0.032 Uiso 1 1 calc R U . . . C4 C 0.19075(19) 0.30657(7) 0.51803(16) 0.0263(3) Uani 1 1 d . . . . . H4A H 0.154180 0.292572 0.613210 0.032 Uiso 1 1 calc R U . . . H4B H 0.314996 0.290573 0.531209 0.032 Uiso 1 1 calc R U . . . C5 C 0.18540(19) 0.38054(6) 0.50475(17) 0.0238(3) Uani 1 1 d . . . . . H5A H 0.127122 0.399843 0.581189 0.029 Uiso 1 1 calc R U . . . H5B H 0.308948 0.398626 0.526496 0.029 Uiso 1 1 calc R U . . . C6 C 0.07476(18) 0.39111(6) 0.33329(16) 0.0201(3) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.02088(18) 0.01868(18) 0.01866(17) -0.00043(10) 0.00464(13) -0.00007(11) O1 0.0386(6) 0.0194(5) 0.0287(5) 0.0013(4) 0.0014(4) 0.0044(4) O2 0.0258(5) 0.0221(5) 0.0277(5) -0.0021(4) 0.0032(4) -0.0049(4) O3 0.0254(5) 0.0531(7) 0.0207(5) -0.0011(4) 0.0085(4) 0.0004(4) C7 0.0197(6) 0.0198(6) 0.0189(6) -0.0007(5) 0.0070(5) -0.0008(5) C8 0.0276(7) 0.0187(6) 0.0239(6) -0.0017(5) 0.0067(5) -0.0026(5) C9 0.0274(7) 0.0221(7) 0.0240(7) 0.0031(5) 0.0068(6) 0.0005(5) C10 0.0193(6) 0.0281(7) 0.0195(6) -0.0004(5) 0.0074(5) 0.0004(5) C11 0.0274(7) 0.0362(8) 0.0213(7) -0.0001(6) 0.0050(6) 0.0008(6) C12 0.0257(7) 0.0225(7) 0.0231(6) -0.0053(5) 0.0090(5) -0.0026(5) C13 0.0263(7) 0.0173(6) 0.0225(6) -0.0008(5) 0.0089(5) 0.0001(5) N1 0.0281(6) 0.0180(6) 0.0243(6) -0.0007(4) 0.0051(5) -0.0021(4) N2 0.0283(6) 0.0191(5) 0.0194(5) 0.0009(4) 0.0034(5) -0.0014(4) C1 0.0369(8) 0.0218(7) 0.0200(6) 0.0006(5) 0.0049(6) 0.0003(6) C2 0.0277(7) 0.0225(7) 0.0185(6) 0.0004(5) 0.0037(5) -0.0016(5) C3 0.0345(8) 0.0205(7) 0.0235(7) 0.0022(5) 0.0056(6) 0.0021(5) C4 0.0267(7) 0.0275(7) 0.0229(7) 0.0044(5) 0.0049(5) -0.0012(5) C5 0.0216(7) 0.0265(7) 0.0215(7) -0.0030(5) 0.0040(5) 0.0017(5) C6 0.0185(6) 0.0219(6) 0.0211(6) -0.0011(5) 0.0078(5) -0.0002(5) 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' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 0 0.0250 0 -1 0 0.0217 0 -1 -2 0.0511 2 1 1 0.0726 -2 2 1 0.0580 2 1 2 0.0700 -4 0 5 0.0742 3 9 -4 0.0651 -1 12 2 0.0395 -3 11 2 0.0450 0 11 -3 0.0380 -4 7 1 0.0550 -5 1 2 0.0571 5 5 -1 0.0745 2 7 4 0.0636 -5 -5 2 0.0560 0 -6 -5 0.0459 1 9 4 0.0558 4 8 0 0.0656 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 O1 S1 O2 112.24(6) . . ? O1 S1 C7 106.48(6) . . ? O2 S1 C7 105.13(6) . . ? O3 S1 O1 113.59(6) . . ? O3 S1 O2 112.54(6) . . ? O3 S1 C7 106.09(6) . . ? C8 C7 S1 119.88(10) . . ? C8 C7 C13 119.71(12) . . ? C13 C7 S1 120.29(10) . . ? C7 C8 H8 120.0 . . ? C9 C8 C7 119.94(12) . . ? C9 C8 H8 120.0 . . ? C8 C9 H9 119.4 . . ? C8 C9 C10 121.15(12) . . ? C10 C9 H9 119.4 . . ? C9 C10 C11 121.25(12) . . ? C9 C10 C12 118.22(12) . . ? C12 C10 C11 120.49(12) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12 119.4 . . ? C13 C12 C10 121.18(12) . . ? C13 C12 H12 119.4 . . ? C7 C13 H13 120.1 . . ? C12 C13 C7 119.78(12) . . ? C12 C13 H13 120.1 . . ? C1 N1 H1 123.7(10) . . ? C6 N1 H1 126.0(11) . . ? C6 N1 C1 109.92(11) . . ? C3 N2 C2 133.72(11) . . ? C6 N2 C2 111.60(11) . . ? C6 N2 C3 114.37(11) . . ? N1 C1 H1A 111.1 . . ? N1 C1 H1B 111.1 . . ? N1 C1 C2 103.50(10) . . ? H1A C1 H1B 109.0 . . ? C2 C1 H1A 111.1 . . ? C2 C1 H1B 111.1 . . ? N2 C2 C1 101.65(10) . . ? N2 C2 H2A 111.4 . . ? N2 C2 H2B 111.4 . . ? C1 C2 H2A 111.4 . . ? C1 C2 H2B 111.4 . . ? H2A C2 H2B 109.3 . . ? N2 C3 H3A 111.2 . . ? N2 C3 H3B 111.2 . . ? N2 C3 C4 102.59(11) . . ? H3A C3 H3B 109.2 . . ? C4 C3 H3A 111.2 . . ? C4 C3 H3B 111.2 . . ? C3 C4 H4A 110.3 . . ? C3 C4 H4B 110.3 . . ? H4A C4 H4B 108.6 . . ? C5 C4 C3 107.02(11) . . ? C5 C4 H4A 110.3 . . ? C5 C4 H4B 110.3 . . ? C4 C5 H5A 111.3 . . ? C4 C5 H5B 111.3 . . ? H5A C5 H5B 109.2 . . ? C6 C5 C4 102.50(11) . . ? C6 C5 H5A 111.3 . . ? C6 C5 H5B 111.3 . . ? N1 C6 N2 113.25(12) . . ? N1 C6 C5 134.12(12) . . ? N2 C6 C5 112.59(11) . . ? 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 O1 1.4496(10) . ? S1 O2 1.4625(9) . ? S1 O3 1.4471(11) . ? S1 C7 1.7766(13) . ? C7 C8 1.3922(18) . ? C7 C13 1.3930(18) . ? C8 H8 0.9500 . ? C8 C9 1.3893(19) . ? C9 H9 0.9500 . ? C9 C10 1.3951(19) . ? C10 C11 1.5087(18) . ? C10 C12 1.3955(19) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12 0.9500 . ? C12 C13 1.3915(19) . ? C13 H13 0.9500 . ? N1 H1 0.907(13) . ? N1 C1 1.4742(17) . ? N1 C6 1.3089(17) . ? N2 C2 1.4647(16) . ? N2 C3 1.4550(17) . ? N2 C6 1.3122(17) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C1 C2 1.5480(19) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C3 C4 1.5439(19) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4 C5 1.5437(18) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C5 C6 1.4816(18) . ? 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 S1 C7 C8 C9 176.44(10) . . . . ? S1 C7 C13 C12 -176.14(10) . . . . ? O1 S1 C7 C8 155.59(11) . . . . ? O1 S1 C7 C13 -28.42(13) . . . . ? O2 S1 C7 C8 36.33(12) . . . . ? O2 S1 C7 C13 -147.69(11) . . . . ? O3 S1 C7 C8 -83.10(12) . . . . ? O3 S1 C7 C13 92.88(12) . . . . ? C7 C8 C9 C10 0.3(2) . . . . ? C8 C7 C13 C12 -0.1(2) . . . . ? C8 C9 C10 C11 176.70(12) . . . . ? C8 C9 C10 C12 -1.2(2) . . . . ? C9 C10 C12 C13 1.5(2) . . . . ? C10 C12 C13 C7 -0.9(2) . . . . ? C11 C10 C12 C13 -176.42(12) . . . . ? C13 C7 C8 C9 0.4(2) . . . . ? N1 C1 C2 N2 -2.81(13) . . . . ? N2 C3 C4 C5 9.53(14) . . . . ? C1 N1 C6 N2 -0.36(17) . . . . ? C1 N1 C6 C5 -177.72(14) . . . . ? C2 N2 C3 C4 179.94(13) . . . . ? C2 N2 C6 N1 -1.73(17) . . . . ? C2 N2 C6 C5 176.22(11) . . . . ? C3 N2 C2 C1 175.83(14) . . . . ? C3 N2 C6 N1 -176.17(12) . . . . ? C3 N2 C6 C5 1.78(17) . . . . ? C3 C4 C5 C6 -8.63(14) . . . . ? C4 C5 C6 N1 -178.07(15) . . . . ? C4 C5 C6 N2 4.55(15) . . . . ? C6 N1 C1 C2 2.10(15) . . . . ? C6 N2 C2 C1 2.85(14) . . . . ? C6 N2 C3 C4 -7.23(15) . . . . ? loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -0.0000 1.0007 0.0012 0.0048 -0.0737 0.0062 0.0000 -1.0007 -0.0012 -0.0048 0.0737 -0.0062 0.0029 -0.9908 -2.0042 0.2615 0.0689 -0.2708 1.9984 0.9944 1.0058 -0.4989 -0.1116 -0.0522 -2.0035 2.0063 0.9997 0.2475 -0.1053 0.3356 2.0028 0.9924 1.9981 -0.6319 -0.1095 0.0784 -3.9948 0.0349 5.0067 0.0727 0.0879 1.0428 3.0076 8.9686 -4.0145 0.0221 -0.7289 -0.7629 -0.9824 12.0041 1.9897 -0.0241 -0.8600 0.4294 -3.0005 11.0101 1.9984 0.3433 -0.7461 0.6173 -0.0005 10.9965 -3.0062 0.4545 -0.8155 -0.3300 -4.0036 7.0054 1.0020 0.6420 -0.4330 0.5574 -5.0042 1.0057 2.0058 0.6640 0.0309 0.7490 5.0039 4.9992 -1.0072 -0.7674 -0.4710 -0.5808 2.0014 7.0128 3.9985 -0.8684 -0.5488 0.3791 -4.9980 -4.9888 2.0031 0.6337 0.4721 0.7117 0.0032 -5.9830 -5.0010 0.6360 0.4305 -0.6967 0.9977 8.9821 4.0020 -0.6734 -0.6735 0.4874 3.9997 7.9875 0.0040 -0.7015 -0.6688 -0.3332