#------------------------------------------------------------------------------ #$Date: 2024-09-28 01:07:40 +0300 (Sat, 28 Sep 2024) $ #$Revision: 294924 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/27/1572700.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_1572700 loop_ _publ_author_name 'Sun, Huili' 'Zhang, Qiang-Sheng' 'Wang, Zhonghao' 'Huang, Yan-Ting' 'Pan, Mei' _publ_section_title ; Long-Persistent Luminescence by Host-Guest F\"orster Resonance Energy Transfer ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC04746J _journal_year 2024 _chemical_formula_moiety 'C22 H10 N2 O4 S2, 2(C2 H5 N)' _chemical_formula_sum 'C26 H20 N4 O4 S2' _chemical_formula_weight 516.58 _chemical_name_systematic DTST _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 mixed _atom_sites_solution_primary iterative _audit_creation_date 2023-12-06 _audit_creation_method ; Olex2 1.5 (compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748) ; _audit_update_record ; 2023-12-06 deposited with the CCDC. 2024-09-20 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 103.976(9) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 16.7130(15) _cell_length_b 8.6188(10) _cell_length_c 9.3560(8) _cell_measurement_reflns_used 1822 _cell_measurement_temperature 240.00(10) _cell_measurement_theta_max 60.8850 _cell_measurement_theta_min 5.7340 _cell_volume 1307.8(2) _computing_cell_refinement 'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)' _computing_data_collection 'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)' _computing_data_reduction 'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2013/2 (Sheldrick, 2015)' _computing_structure_solution 'olex2.solve 1.5 (Bourhis et al., 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 240.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.6525 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.575 _diffrn_measured_fraction_theta_max 0.995 _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 -20.00 32.00 1.00 7.50 -- 0.00 -77.00 -90.00 52 2 \w -33.00 1.00 1.00 7.50 -- 0.00 77.00 150.00 34 3 \w 11.00 42.00 1.00 7.50 -- 0.00 77.00 150.00 31 4 \w 46.00 112.00 1.00 13.40 -- 80.51-125.00 -30.00 66 5 \w 22.00 105.00 1.00 13.40 -- 80.51 -61.00 120.00 83 6 \w 103.00 153.00 1.00 13.40 -- 80.51 77.00 120.00 50 7 \w 111.00 154.00 1.00 13.40 -- 80.51 125.00 90.00 43 8 \w 54.00 151.00 1.00 13.40 -- 80.51 61.00 -90.00 97 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0908953000 _diffrn_orient_matrix_UB_12 -0.0415939000 _diffrn_orient_matrix_UB_13 0.0099236000 _diffrn_orient_matrix_UB_21 -0.0221288000 _diffrn_orient_matrix_UB_22 -0.1737983000 _diffrn_orient_matrix_UB_23 -0.0075463000 _diffrn_orient_matrix_UB_31 -0.0165399000 _diffrn_orient_matrix_UB_32 0.0054153000 _diffrn_orient_matrix_UB_33 -0.1691367000 _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 0.0190 _diffrn_reflns_av_unetI/netI 0.0239 _diffrn_reflns_Laue_measured_fraction_full 0.575 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 2593 _diffrn_reflns_point_group_measured_fraction_full 0.575 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 50.382 _diffrn_reflns_theta_min 5.814 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.171 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.50559 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light black' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary black _exptl_crystal_density_diffrn 1.312 _exptl_crystal_description block _exptl_crystal_F_000 536 _exptl_crystal_preparation 1 _exptl_crystal_recrystallization_method 1 _exptl_crystal_size_max 0.01 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.224 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.041 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 172 _refine_ls_number_reflns 1363 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 1.119 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0471 _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^)+(0.0659P)^2^+0.7600P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1245 _refine_ls_wR_factor_ref 0.1310 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1202 _reflns_number_total 1363 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc04746j10.cif _cod_data_source_block DTST _cod_database_code 1572700 _shelxl_version_number 2013-2 _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. ; _reflns_odcompleteness_completeness 98.38 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 58.86 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances C-HB 0.96 with sigma of 0.02 C-HA 0.96 with sigma of 0.02 C00I-H00E 0.96 with sigma of 0.02 C00I-H00A 0.96 with sigma of 0.02 3.a Aromatic/amide H refined with riding coordinates: C004(H004), C006(H006), C009(H009), C00B(H00B), C00C(H00C) 3.b Idealised Me refined as rotating group: C00I(H00A,H00D,H00E) ; _shelx_res_file ; TITL exp_6239_auto_a.res in P2(1)/c REM Old TITL exp_6239_auto_a.res in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.219, Rweak 0.007, Alpha 0.056, Orientation as input REM Formula found by SHELXT: C26 H20 N4 O4 S2 CELL 1.54184 16.713 8.6188 9.356 90 103.976 90 ZERR 2 0.0015 0.001 0.0008 0 0.009 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O S UNIT 52 40 8 8 4 DFIX 0.96 C Hb DFIX 0.96 C Ha DFIX 0.96 C00I H00e DFIX 0.96 C00I H00a L.S. 10 PLAN 1 TEMP -33 CONF BOND $H list 4 MORE -1 fmap 2 acta SHEL 999 1 REM REM REM WGHT 0.065900 0.760000 FVAR 0.49873 S001 5 0.977651 0.657639 0.685604 11.00000 0.05043 0.10404 = 0.05750 0.02369 0.01071 -0.00598 N002 3 0.812621 0.318699 1.131831 11.00000 0.06656 0.08609 = 0.08231 -0.00944 0.03191 -0.01541 C003 1 0.986412 0.569925 0.859228 11.00000 0.04587 0.05264 = 0.04649 0.00052 0.01288 0.00320 C004 1 0.921739 0.503388 0.906069 11.00000 0.03941 0.06031 = 0.04794 0.00036 0.00881 0.00052 AFIX 43 H004 2 0.868355 0.504540 0.843925 11.00000 -1.20000 AFIX 0 C005 1 0.935229 0.434947 1.044292 11.00000 0.04063 0.05189 = 0.04735 -0.00384 0.01412 -0.00205 C006 1 0.762797 0.523551 0.419303 11.00000 0.06209 0.08450 = 0.04887 -0.00366 0.01564 -0.00383 AFIX 43 H006 2 0.745063 0.448491 0.345561 11.00000 -1.20000 AFIX 0 C007 1 0.866026 0.369294 1.090938 11.00000 0.04655 0.06397 = 0.05295 -0.00490 0.01058 -0.00112 C008 1 0.871463 0.640744 0.600055 11.00000 0.04989 0.06881 = 0.04435 0.01304 0.01250 0.00340 C009 1 0.732885 0.733832 0.561933 11.00000 0.06226 0.08227 = 0.06088 0.00810 0.02080 0.02150 AFIX 43 H009 2 0.694719 0.802897 0.586326 11.00000 -1.20000 AFIX 0 O00A 4 0.569112 0.716806 0.395813 11.00000 0.06215 0.21292 = 0.09970 0.01648 0.01446 0.04226 C00B 1 0.845005 0.530635 0.491774 11.00000 0.05453 0.06986 = 0.05575 0.00607 0.01973 0.00948 AFIX 43 H00B 2 0.882876 0.460790 0.467556 11.00000 -1.20000 AFIX 0 C00C 1 0.814824 0.742809 0.635214 11.00000 0.06540 0.07202 = 0.05226 -0.00228 0.01409 0.00483 AFIX 43 H00C 2 0.832378 0.817951 0.708945 11.00000 -1.20000 AFIX 0 C00D 1 0.706266 0.624507 0.453099 11.00000 0.05090 0.08994 = 0.04256 0.01200 0.01172 0.00771 O00E 4 0.594952 0.503411 0.286383 11.00000 0.07317 0.22665 = 0.10048 -0.05111 -0.01057 -0.01124 C00F 1 0.615765 0.613572 0.371017 11.00000 0.05565 0.16132 = 0.05902 0.02057 0.01370 0.00833 N00 3 0.429260 0.586387 0.180799 11.00000 0.05723 0.42604 = 0.06943 0.06806 0.00241 -0.03223 C 1 0.414800 0.640179 0.048183 11.00000 0.06887 0.21553 = 0.10457 0.04749 0.03011 0.00242 C00I 1 0.369594 0.554875 0.256479 11.00000 0.19236 0.18065 = 0.09653 -0.02363 0.06845 -0.08080 AFIX 137 H00A 2 0.315576 0.557599 0.188741 11.00000 -1.50000 H00D 2 0.372167 0.632132 0.332848 11.00000 -1.50000 H00E 2 0.379169 0.452780 0.300957 11.00000 -1.50000 AFIX 0 HA 2 0.360213 0.637622 -0.004766 11.00000 0.12283 HB 2 0.461236 0.670847 0.023529 11.00000 0.11554 HKLF 4 REM exp_6239_auto_a.res in P2(1)/c REM R1 = 0.0471 for 1202 Fo > 4sig(Fo) and 0.0535 for all 1363 data REM 172 parameters refined using 4 restraints END WGHT 0.0659 0.7606 REM Highest difference peak 0.224, deepest hole -0.196, 1-sigma level 0.041 Q1 1 0.4346 0.5135 0.1084 11.00000 0.05 0.22 ; _shelx_res_checksum 34357 _shelx_hkl_file ; 0 0 1 0.03 0.10 0 0 -1 0.07 0.10 0 0 2 42.08 1.45 0 0 2 39.95 1.28 0 0 3 0.36 0.35 0 0 3 0.02 0.22 0 0 -4 571.32 6.53 0 0 -4 561.21 6.20 0 0 4 553.78 7.71 0 0 4 553.63 8.72 0 0 -5 -0.01 0.22 0 0 -6 1.43 0.50 0 0 -7 2.23 0.78 0 0 -8 28.82 1.99 0 0 -9 0.15 0.35 0 -1 1 19.40 0.63 0 1 -1 20.12 0.43 0 -1 2 17.76 0.96 0 1 -2 18.40 0.96 0 1 -3 15.03 1.12 0 -1 3 15.58 1.15 0 1 3 12.89 1.10 0 -1 -4 335.88 4.88 0 1 -4 347.11 4.63 0 1 4 357.26 7.01 0 -1 4 340.64 6.09 0 1 -4 343.05 4.92 0 1 4 330.53 5.95 0 1 -5 119.54 3.05 0 -1 -5 117.21 3.11 0 1 -5 112.18 3.09 0 -1 -6 122.96 3.63 0 1 -6 130.60 3.62 0 1 -6 121.82 3.55 0 1 -7 8.05 1.04 0 -1 -7 8.18 1.10 0 -1 -8 0.50 0.69 0 1 -8 0.48 0.54 0 1 -9 0.93 0.40 0 -1 -9 2.20 0.74 0 1 -10 15.40 1.24 0 2 0 197.40 2.57 0 2 1 257.25 3.77 0 2 2 0.52 0.31 0 2 -2 0.72 0.36 0 2 -3 50.08 2.12 0 -2 3 50.10 1.75 0 2 3 49.12 2.29 0 2 -4 155.61 3.47 0 -2 -4 162.84 3.43 0 2 -4 162.10 3.34 0 2 -4 167.87 3.11 0 2 -4 165.57 4.48 0 2 -5 147.45 3.36 0 2 -5 139.84 3.69 0 -2 -5 140.46 3.57 0 2 -5 140.92 3.50 0 2 -6 1.10 0.50 0 -2 -6 1.03 0.54 0 2 -6 0.37 0.32 0 -2 -7 12.07 1.42 0 2 -7 8.99 1.08 0 2 -8 3.15 0.81 0 2 -9 18.95 1.56 0 3 0 0.19 0.16 0 3 1 15.52 1.04 0 3 -2 246.74 5.12 0 3 2 231.03 4.88 0 3 -3 232.29 5.34 0 3 -3 225.98 4.34 0 3 -4 147.49 2.99 0 3 -4 147.59 3.84 0 3 -5 0.27 0.33 0 3 -5 0.76 0.36 0 3 -6 0.67 0.44 0 3 -6 0.09 0.35 0 3 -7 -0.49 0.52 0 3 -7 0.53 0.37 0 3 -8 1.03 0.52 0 3 -9 4.77 0.82 0 4 0 4.68 0.55 0 4 1 168.33 4.08 0 4 2 6.40 0.82 0 4 -2 9.85 0.95 0 4 -3 37.92 2.01 0 4 -4 5.66 0.89 0 4 -5 4.09 0.80 0 4 -5 3.55 0.62 0 4 -6 15.47 1.63 0 4 -6 14.15 1.35 0 4 -7 -0.11 0.62 0 4 -7 0.91 0.51 0 4 -8 10.56 1.18 0 -4 8 9.25 1.14 0 4 -9 9.52 1.02 0 -5 0 -0.10 0.32 0 -5 1 12.06 1.15 0 -5 -1 12.15 1.02 0 -5 2 33.73 1.94 0 -5 -2 31.58 1.66 0 5 -3 1.39 0.56 0 5 -4 31.57 2.29 0 5 -5 23.14 1.77 0 5 -5 25.96 2.21 0 5 -6 20.13 1.62 0 5 -6 19.38 1.96 0 5 -7 5.63 0.90 0 -5 7 3.49 0.83 0 5 -8 -0.18 0.35 0 -5 8 0.45 0.42 0 -6 0 55.22 2.49 0 -6 -1 1.32 0.50 0 -6 1 1.19 0.41 0 -6 -2 12.18 1.14 0 -6 2 12.99 1.38 0 -6 3 -0.56 0.55 0 -6 4 0.03 0.46 0 -6 5 1.71 0.67 0 6 -5 2.30 0.61 0 -6 6 0.01 0.49 0 6 -6 0.43 0.32 0 -6 7 2.64 0.66 0 6 -7 4.02 0.72 0 -7 0 0.90 0.43 0 -7 1 8.10 1.08 0 -7 -1 10.30 1.17 0 -7 2 0.06 0.41 0 -7 3 5.87 1.02 0 -7 4 11.30 1.36 0 7 -5 6.77 0.92 0 -7 5 7.92 1.20 0 -7 6 6.57 1.02 0 -7 7 1.67 0.52 0 -8 0 1.39 0.51 0 -8 1 4.54 0.88 0 -8 2 7.32 1.10 0 -8 3 1.87 0.67 0 -8 4 3.59 0.76 0 -8 5 2.44 0.64 0 -9 1 0.94 0.56 0 -9 2 7.19 1.02 0 -9 3 3.39 0.71 1 0 -10 8.42 1.05 1 0 -9 -0.15 0.41 1 0 -8 13.23 1.38 1 0 -7 0.45 0.41 1 0 -6 204.76 4.65 1 0 -5 -0.39 0.34 1 0 -5 0.13 0.20 -1 0 4 134.75 3.80 -1 0 4 135.37 3.74 -1 0 3 -0.12 0.21 -1 0 3 0.00 0.22 -1 0 2 55.07 1.66 -1 0 2 55.36 1.52 -1 0 1 0.07 0.14 -1 0 -1 0.07 0.09 -1 0 -1 -0.02 0.15 1 0 1 0.07 0.09 -1 0 -2 121.81 2.39 1 0 2 132.07 2.23 -1 0 -3 -0.02 0.24 1 0 3 0.01 0.18 1 0 4 214.24 4.30 -1 0 -4 217.00 3.77 -1 0 -5 -0.04 0.28 -1 0 -5 0.00 0.26 -1 0 -6 1.01 0.39 -1 0 -6 0.88 0.27 -1 0 -7 0.87 0.59 -1 0 -8 17.22 1.54 -1 0 -9 0.45 0.40 1 1 -10 2.54 0.57 1 1 -9 3.55 0.80 1 -1 -9 3.03 0.76 1 -1 -8 6.44 1.09 1 1 -8 5.67 0.99 1 1 -7 2.42 0.56 1 -1 -7 5.31 0.87 1 1 -6 3.00 0.56 1 -1 -6 2.82 0.61 1 1 -5 354.49 5.34 1 1 -5 362.84 5.69 -1 1 4 345.62 6.45 1 -1 -4 339.18 4.84 1 1 -4 339.99 4.86 -1 -1 4 335.94 6.14 -1 1 4 340.77 6.54 1 1 -3 384.94 5.96 -1 1 3 377.10 5.88 -1 -1 3 377.53 5.72 -1 -1 3 375.39 4.98 -1 -1 2 775.08 6.38 -1 -1 2 769.76 7.63 -1 -1 1 25.19 0.94 -1 -1 0 489.03 4.11 -1 -1 -1 219.10 2.97 -1 1 -1 193.85 2.97 -1 1 -2 39.71 1.27 -1 -1 -2 41.59 1.55 1 -1 2 44.81 1.77 -1 1 -2 43.56 1.42 1 1 3 131.10 3.05 1 1 3 125.76 3.69 -1 1 -3 118.69 2.81 -1 1 -3 121.21 2.98 -1 -1 -4 43.36 1.66 1 -1 4 47.50 2.98 -1 1 -4 48.64 1.72 1 1 4 42.26 1.88 -1 1 -5 68.94 2.45 -1 1 -5 68.55 2.37 -1 -1 -5 72.17 2.45 -1 -1 -5 72.63 2.39 -1 -1 -6 5.83 0.78 -1 1 -6 5.15 0.74 -1 1 -6 5.81 0.83 -1 1 -7 0.31 0.46 -1 -1 -7 1.07 0.61 -1 1 -8 1.43 0.65 -1 -1 -8 2.34 0.85 -1 1 -9 8.06 1.02 1 2 -10 1.72 0.46 1 2 -9 6.45 0.98 1 2 -8 2.44 0.76 1 -2 -8 5.40 1.24 1 -2 -7 16.93 1.56 1 2 -7 14.33 1.36 1 2 -6 29.17 1.77 1 -2 -6 32.90 1.91 1 2 -6 33.67 1.88 1 2 -5 102.06 2.95 1 -2 -5 97.88 2.94 1 2 -5 103.05 2.73 1 2 -5 101.49 3.02 1 2 -4 17.95 0.99 1 -2 -4 17.22 1.08 1 2 -3 160.51 3.87 -1 -2 3 158.38 2.69 -1 2 3 157.70 3.90 1 2 -2 4294.06 29.87 -1 2 2 4320.54 29.82 1 2 0 3.80 0.37 -1 2 -1 154.03 2.56 1 2 1 143.78 2.84 1 2 2 8.44 0.89 -1 2 -2 10.38 0.58 -1 2 -2 10.17 0.86 1 2 3 270.08 5.83 -1 2 -3 274.92 5.02 1 2 4 71.74 2.81 -1 2 -4 75.48 2.42 -1 -2 -4 73.72 2.29 -1 2 -4 76.00 2.27 -1 2 -4 74.62 2.91 -1 2 -5 0.51 0.29 -1 -2 -5 0.72 0.42 -1 2 -5 0.78 0.40 -1 2 -6 11.80 1.11 -1 2 -6 12.52 1.28 -1 -2 -6 14.42 1.33 -1 2 -7 52.54 2.77 -1 2 -7 44.23 2.39 -1 -2 -7 47.28 2.61 -1 2 -8 10.93 1.26 -1 2 -9 3.94 0.71 1 3 -9 0.59 0.51 1 3 -8 0.04 0.36 1 3 -7 70.28 3.14 1 3 -6 0.97 0.46 1 3 -6 0.39 0.29 1 3 -5 40.25 2.10 1 3 -5 38.80 1.90 1 3 -5 38.53 1.70 1 3 -4 4.62 0.50 1 3 -4 5.17 0.75 -1 3 3 138.63 4.06 1 3 -3 134.56 3.24 -1 3 2 78.19 2.67 1 3 -2 84.75 2.94 -1 3 1 131.58 2.98 1 3 1 51.87 1.92 -1 3 -2 189.22 4.49 1 3 2 150.18 4.05 -1 3 -3 358.29 6.56 -1 3 -3 352.89 5.62 -1 3 -4 17.12 1.18 -1 3 -4 17.86 1.31 -1 3 -5 182.44 4.19 -1 3 -5 184.40 4.74 -1 3 -6 3.56 0.71 -1 3 -6 3.44 0.81 -1 3 -7 8.20 1.05 -1 3 -7 9.56 1.25 -1 3 -8 1.15 0.51 -1 3 -9 11.43 1.11 1 4 -9 17.43 1.40 1 4 -8 -0.11 0.50 1 4 -7 5.93 0.94 1 4 -7 5.04 0.96 1 4 -6 14.79 1.39 1 4 -6 17.13 1.74 1 4 -5 22.95 1.66 1 4 -5 28.02 1.98 1 4 -4 11.87 1.24 1 4 -3 91.98 3.08 -1 4 2 219.84 5.18 1 4 -2 183.51 4.20 -1 4 1 61.01 2.32 -1 -4 1 55.34 2.15 -1 4 0 70.19 2.09 -1 -4 0 61.43 2.11 1 4 1 4.27 0.69 -1 4 -1 5.20 0.66 -1 -4 -1 5.69 0.66 -1 -4 -2 35.99 1.66 1 4 2 34.54 2.22 -1 4 -2 37.34 1.84 -1 4 -3 26.27 1.68 -1 -4 -3 24.78 1.39 -1 4 -4 5.23 0.82 -1 4 -5 0.66 0.58 -1 4 -5 0.44 0.27 -1 4 -6 0.07 0.34 -1 4 -6 0.51 0.50 -1 4 -7 -0.21 0.56 -1 4 -7 0.36 0.41 -1 4 -8 57.15 2.58 1 5 -8 0.70 0.31 -1 -5 7 0.72 0.68 1 5 -7 1.02 0.45 1 5 -6 16.90 1.55 -1 -5 6 17.63 1.77 -1 -5 5 2.16 0.70 -1 -5 4 8.53 1.13 -1 -5 3 3.03 0.69 -1 -5 2 23.07 1.63 -1 -5 1 4.43 0.72 1 -5 -1 4.46 0.66 1 -5 0 39.75 1.96 -1 -5 0 36.41 1.87 1 -5 1 0.60 0.44 -1 -5 -1 -0.51 0.34 -1 -5 -2 181.57 4.21 -1 5 -2 178.70 4.78 -1 5 -3 7.20 1.08 -1 5 -4 78.86 3.52 -1 5 -5 18.61 1.86 -1 5 -5 17.96 1.50 -1 5 -6 3.99 0.95 -1 5 -6 3.14 0.66 -1 5 -7 -0.13 0.45 -1 5 -7 0.31 0.59 1 -5 8 6.42 0.92 1 6 -7 0.60 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1.03 0.46 -15 -1 -1 0.27 0.34 15 1 2 1.61 0.54 -15 -1 -2 2.91 0.62 -15 1 -3 0.85 0.41 -15 -1 -3 1.01 0.40 -15 1 -4 9.33 0.96 -15 -1 -4 10.14 0.98 15 2 -7 31.58 1.87 15 2 -6 13.14 1.31 15 2 -6 12.10 1.25 15 2 -5 102.56 3.69 15 -2 -5 99.55 3.47 15 2 -5 107.30 3.87 15 -2 -4 1.22 0.44 15 2 -4 2.20 0.60 15 -2 -3 44.41 2.29 15 2 -3 42.45 2.52 15 -2 -2 3.03 0.62 15 2 -2 2.24 0.62 15 2 -1 9.18 1.18 15 2 0 2.43 0.60 -15 -2 -1 0.64 0.50 -15 -2 -2 7.43 0.95 -15 2 -3 32.45 1.90 -15 -2 -3 31.25 1.86 15 3 -7 15.19 1.31 15 3 -6 6.22 0.88 15 3 -6 8.01 1.04 15 3 -5 -0.18 0.45 15 3 -5 0.42 0.41 15 3 -4 1.56 0.57 15 3 -3 48.99 2.77 15 3 -2 9.64 1.22 15 3 -1 26.88 2.06 -15 -3 1 28.16 1.88 -15 -3 0 3.11 0.69 -15 -3 -1 13.14 1.29 -15 -3 -2 4.75 0.80 -15 -3 -3 0.00 0.26 15 4 -6 2.24 0.61 15 4 -5 -0.66 0.49 15 4 -5 0.19 0.45 15 4 -4 1.14 0.44 15 4 -3 4.74 0.97 15 4 -2 7.66 1.18 -15 -4 2 6.22 0.88 15 4 -1 0.09 0.41 -15 -4 1 0.74 0.37 -15 -4 0 -0.50 0.37 15 4 0 -0.57 0.57 -15 -4 -1 5.02 0.83 -15 -4 -2 22.84 1.60 15 5 -5 1.39 0.52 15 5 -4 0.53 0.35 15 5 -3 0.66 0.45 -15 -5 2 17.46 1.36 15 5 -2 22.10 1.81 15 5 -1 0.53 0.35 -15 -5 1 1.17 0.43 -15 -5 0 1.58 0.48 15 5 0 2.01 0.62 -15 -5 0 2.34 0.54 16 0 -7 0.45 0.27 16 0 -6 114.24 3.27 16 0 -6 123.55 3.85 16 0 -5 0.05 0.34 16 0 -5 -0.63 0.39 16 0 -4 58.43 2.43 16 0 -4 63.14 2.93 16 0 -3 -0.77 0.58 16 0 -2 4.54 0.79 16 0 -1 0.20 0.31 16 0 0 3.31 0.65 -16 0 -2 53.38 2.41 -16 0 -3 0.51 0.38 16 1 -7 3.35 0.61 16 1 -6 3.33 0.69 16 1 -6 3.42 0.66 16 1 -5 9.79 1.05 16 -1 -5 10.75 1.13 16 1 -5 9.74 1.12 16 -1 -4 2.28 0.56 16 1 -4 1.77 0.47 16 -1 -3 1.35 0.47 16 1 -3 1.52 0.49 16 -1 -2 57.80 2.63 16 1 -2 57.79 2.72 16 -1 -1 40.87 2.12 16 1 -1 40.72 2.26 16 1 0 14.87 1.35 16 1 1 -0.11 0.32 16 1 2 -0.16 0.35 -16 -1 -2 1.08 0.44 16 2 -7 11.30 1.09 16 2 -6 0.51 0.44 16 2 -6 0.27 0.32 16 2 -5 15.92 1.41 16 2 -5 17.25 1.50 16 -2 -4 2.34 0.59 16 2 -4 1.14 0.42 16 -2 -3 0.37 0.27 16 2 -3 0.66 0.44 16 2 -2 8.06 1.09 16 2 -1 -0.12 0.39 16 2 0 0.75 0.31 16 2 1 6.84 0.92 -16 -2 -1 8.38 0.98 16 2 2 9.88 1.08 -16 -2 -2 9.73 1.03 16 3 -6 10.86 1.14 16 3 -6 8.16 0.94 16 3 -5 -0.38 0.41 16 3 -5 -0.59 0.48 16 3 -4 7.60 1.06 16 3 -3 53.85 2.76 16 3 -2 16.63 1.52 16 3 -1 1.20 0.48 16 3 0 1.72 0.57 16 3 1 3.00 0.66 -16 -3 -1 2.89 0.61 16 3 2 0.90 0.40 16 4 -5 0.43 0.35 16 4 -5 1.44 0.51 16 4 -4 1.89 0.54 16 4 -3 11.10 1.30 16 4 -2 1.83 0.54 16 4 -1 -1.08 0.53 16 4 0 0.06 0.34 16 4 1 8.89 1.04 16 5 -2 15.81 1.41 16 5 -1 3.45 0.64 17 0 -6 22.84 1.52 17 0 -5 0.15 0.32 17 0 -4 10.07 1.09 17 0 -3 -0.74 0.44 17 0 -2 0.17 0.28 17 0 -1 0.77 0.38 17 0 0 4.89 0.72 17 1 -6 4.55 0.71 17 1 -6 4.94 0.70 17 -1 -5 0.39 0.43 17 1 -5 0.21 0.31 17 1 -5 0.49 0.27 17 -1 -4 0.58 0.29 17 1 -4 -0.25 0.44 17 1 -4 0.07 0.29 17 -1 -3 3.03 0.62 17 1 -3 1.68 0.51 17 -1 -2 13.85 1.21 17 1 -2 15.26 1.33 17 1 -1 25.47 1.69 17 1 0 5.49 0.81 17 1 1 8.48 0.93 17 2 -6 10.75 1.04 17 2 -6 10.81 1.06 17 2 -5 -0.80 0.47 17 2 -5 -0.04 0.30 17 -2 -4 0.19 0.28 17 2 -4 -0.32 0.51 17 -2 -3 5.34 0.71 17 2 -3 3.54 0.66 17 2 -2 5.57 0.85 17 2 -1 2.02 0.53 17 2 0 3.64 0.66 17 2 1 25.60 1.61 17 3 -5 -0.22 0.41 17 3 -5 -0.32 0.38 17 3 -4 1.36 0.51 17 3 -3 56.35 2.57 17 3 -2 2.96 0.63 17 3 -1 7.50 0.95 17 3 0 -0.61 0.41 17 4 -4 2.77 0.63 17 4 -3 8.59 1.03 17 4 -2 1.77 0.51 17 4 -1 -0.25 0.28 18 0 -5 0.00 0.24 18 0 -4 27.56 1.62 18 0 -3 -0.77 0.39 18 0 -2 1.66 0.39 18 0 -1 -1.42 0.45 18 1 -5 0.39 0.31 18 1 -4 8.63 0.86 18 -1 -4 9.71 0.95 18 1 -4 9.66 0.97 18 -1 -3 1.23 0.36 18 1 -3 1.63 0.47 18 1 -2 20.17 1.40 18 1 -1 0.29 0.29 18 2 -4 1.01 0.41 18 2 -4 0.94 0.37 18 2 -3 0.31 0.28 18 2 -2 4.82 0.70 18 2 -1 2.88 0.54 18 3 -3 8.95 0.95 18 3 -2 3.70 0.61 0 0 0 0.00 0.00 TITL exp_6239_auto in P2(1)/c REM P2(1)/c (#14 in standard setting) CELL 1.54184 16.712980 8.618819 9.355977 90.0000 103.9762 90.0000 ZERR 6.00 0.001505 0.000992 0.000820 0.0000 0.0086 0.0000 LATT 1 SYMM -x, y+1/2,-z+1/2 SFAC C H N O UNIT 66.00 60.00 6.00 6.00 REM CrysAlisPro recorded range (K): Min=240.0; max=240.0; aver:240.0 TEMP -33 TREF HKLF 4 END _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' ; _shelx_hkl_checksum 86071 _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 ; _oxdiff_exptl_absorpt_empirical_full_max 2.457 _oxdiff_exptl_absorpt_empirical_full_min 0.762 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 S001 S 0.97765(5) 0.65764(13) 0.68560(10) 0.0711(5) Uani 1 1 d . . . . . N002 N 0.8126(2) 0.3187(4) 1.1318(4) 0.0759(10) Uani 1 1 d . . . . . C003 C 0.98641(19) 0.5699(4) 0.8592(3) 0.0480(8) Uani 1 1 d . . . . . C004 C 0.92174(19) 0.5034(4) 0.9061(3) 0.0495(9) Uani 1 1 d . . . . . H004 H 0.8684 0.5045 0.8439 0.059 Uiso 1 1 calc R U . . . C005 C 0.93523(18) 0.4349(4) 1.0443(3) 0.0460(8) Uani 1 1 d . . . . . C006 C 0.7628(2) 0.5236(5) 0.4193(4) 0.0648(10) Uani 1 1 d . . . . . H006 H 0.7451 0.4485 0.3456 0.078 Uiso 1 1 calc R U . . . C007 C 0.8660(2) 0.3693(4) 1.0909(4) 0.0547(9) Uani 1 1 d . . . . . C008 C 0.8715(2) 0.6407(4) 0.6001(4) 0.0542(10) Uani 1 1 d . . . . . C009 C 0.7329(2) 0.7338(5) 0.5619(4) 0.0675(11) Uani 1 1 d . . . . . H009 H 0.6947 0.8029 0.5863 0.081 Uiso 1 1 calc R U . . . O00A O 0.5691(2) 0.7168(6) 0.3958(4) 0.1258(14) Uani 1 1 d . . . . . C00B C 0.8450(2) 0.5306(4) 0.4918(4) 0.0590(10) Uani 1 1 d . . . . . H00B H 0.8829 0.4608 0.4676 0.071 Uiso 1 1 calc R U . . . C00C C 0.8148(2) 0.7428(5) 0.6352(4) 0.0632(10) Uani 1 1 d . . . . . H00C H 0.8324 0.8180 0.7089 0.076 Uiso 1 1 calc R U . . . C00D C 0.7063(2) 0.6245(5) 0.4531(4) 0.0611(10) Uani 1 1 d . . . . . O00E O 0.5950(2) 0.5034(6) 0.2864(4) 0.1388(17) Uani 1 1 d . . . . . C00F C 0.6158(3) 0.6136(8) 0.3710(5) 0.0920(16) Uani 1 1 d . . . . . N00 N 0.4293(2) 0.5864(10) 0.1808(5) 0.186(3) Uani 1 1 d . . . . . C C 0.4148(4) 0.6402(9) 0.0482(7) 0.128(2) Uani 1 1 d D . . . . C00I C 0.3696(4) 0.5549(8) 0.2565(6) 0.151(3) Uani 1 1 d D . . . . H00A H 0.3156 0.5576 0.1887 0.226 Uiso 1 1 calc DR U . . . H00D H 0.3722 0.6321 0.3328 0.226 Uiso 1 1 calc R U . . . H00E H 0.3792 0.4528 0.3010 0.226 Uiso 1 1 calc DR U . . . HA H 0.3602(16) 0.638(6) -0.005(5) 0.123(18) Uiso 1 1 d D . . . . HB H 0.461(2) 0.671(5) 0.024(5) 0.116(17) Uiso 1 1 d 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 S001 0.0504(7) 0.1040(9) 0.0575(7) 0.0237(5) 0.0107(4) -0.0060(5) N002 0.067(2) 0.086(2) 0.082(2) -0.0094(19) 0.0319(19) -0.0154(19) C003 0.046(2) 0.053(2) 0.0465(19) 0.0005(16) 0.0129(16) 0.0032(16) C004 0.0394(19) 0.060(2) 0.048(2) 0.0004(17) 0.0088(15) 0.0005(16) C005 0.041(2) 0.052(2) 0.047(2) -0.0038(16) 0.0141(16) -0.0021(16) C006 0.062(3) 0.085(3) 0.049(2) -0.0037(19) 0.0156(19) -0.004(2) C007 0.047(2) 0.064(2) 0.053(2) -0.0049(17) 0.0106(18) -0.0011(18) C008 0.050(2) 0.069(2) 0.044(2) 0.0130(19) 0.0125(16) 0.0034(18) C009 0.062(3) 0.082(3) 0.061(2) 0.008(2) 0.021(2) 0.022(2) O00A 0.062(2) 0.213(4) 0.100(2) 0.016(3) 0.0145(17) 0.042(3) C00B 0.055(2) 0.070(3) 0.056(2) 0.006(2) 0.0197(18) 0.0095(19) C00C 0.065(3) 0.072(3) 0.052(2) -0.0023(19) 0.0141(19) 0.005(2) C00D 0.051(2) 0.090(3) 0.043(2) 0.012(2) 0.0117(18) 0.008(2) O00E 0.073(2) 0.227(5) 0.100(3) -0.051(3) -0.0106(19) -0.011(2) C00F 0.056(3) 0.161(5) 0.059(3) 0.021(3) 0.014(2) 0.008(3) N00 0.057(2) 0.426(11) 0.069(3) 0.068(4) 0.002(2) -0.032(4) C 0.069(4) 0.216(7) 0.105(4) 0.047(4) 0.030(3) 0.002(4) C00I 0.192(6) 0.181(6) 0.097(4) -0.024(4) 0.068(4) -0.081(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_ _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 C003 S001 C008 103.44(15) . . ? C004 C003 S001 124.8(2) . . ? C004 C003 C005 117.6(3) . 3_767 ? C005 C003 S001 117.6(2) 3_767 . ? C003 C004 H004 119.8 . . ? C003 C004 C005 120.4(3) . . ? C005 C004 H004 119.8 . . ? C003 C005 C007 119.0(3) 3_767 . ? C004 C005 C003 121.9(3) . 3_767 ? C004 C005 C007 119.0(3) . . ? C00B C006 H006 119.4 . . ? C00D C006 H006 119.4 . . ? C00D C006 C00B 121.1(4) . . ? N002 C007 C005 178.0(4) . . ? C00B C008 S001 119.8(3) . . ? C00B C008 C00C 119.6(3) . . ? C00C C008 S001 120.5(3) . . ? C00C C009 H009 119.7 . . ? C00C C009 C00D 120.7(3) . . ? C00D C009 H009 119.7 . . ? C006 C00B C008 119.7(3) . . ? C006 C00B H00B 120.1 . . ? C008 C00B H00B 120.1 . . ? C008 C00C H00C 120.0 . . ? C009 C00C C008 119.9(4) . . ? C009 C00C H00C 120.0 . . ? C006 C00D C009 119.0(3) . . ? C006 C00D C00F 119.8(4) . . ? C009 C00D C00F 121.2(4) . . ? O00A C00F C00D 116.9(5) . . ? O00E C00F O00A 125.5(5) . . ? O00E C00F C00D 117.6(5) . . ? C N00 C00I 124.9(5) . . ? N00 C HA 116(3) . . ? N00 C HB 112(3) . . ? HA C HB 132(4) . . ? N00 C00I H00A 109.5 . . ? N00 C00I H00D 109.5 . . ? N00 C00I H00E 109.5 . . ? H00A C00I H00D 109.5 . . ? H00A C00I H00E 109.5 . . ? H00D C00I H00E 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 S001 C003 1.765(3) . ? S001 C008 1.768(4) . ? N002 C007 1.139(4) . ? C003 C004 1.385(4) . ? C003 C005 1.400(4) 3_767 ? C004 H004 0.9400 . ? C004 C005 1.389(4) . ? C005 C003 1.400(4) 3_767 ? C005 C007 1.446(5) . ? C006 H006 0.9400 . ? C006 C00B 1.379(5) . ? C006 C00D 1.376(5) . ? C008 C00B 1.381(5) . ? C008 C00C 1.389(5) . ? C009 H009 0.9400 . ? C009 C00C 1.378(5) . ? C009 C00D 1.380(5) . ? O00A C00F 1.241(6) . ? C00B H00B 0.9400 . ? C00C H00C 0.9400 . ? C00D C00F 1.525(6) . ? O00E C00F 1.231(6) . ? N00 C 1.292(7) . ? N00 C00I 1.382(7) . ? C HA 0.93(2) . ? C HB 0.90(2) . ? C00I H00A 0.9700 . ? C00I H00D 0.9700 . ? C00I H00E 0.9700 . ? 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 S001 C003 C004 C005 179.0(2) . . . . ? S001 C008 C00B C006 -176.3(3) . . . . ? S001 C008 C00C C009 176.4(3) . . . . ? C003 S001 C008 C00B -104.1(3) . . . . ? C003 S001 C008 C00C 79.3(3) . . . . ? C003 C004 C005 C003 -0.1(5) . . . 3_767 ? C003 C004 C005 C007 178.8(3) . . . . ? C005 C003 C004 C005 0.1(5) 3_767 . . . ? C006 C00D C00F O00A -173.2(4) . . . . ? C006 C00D C00F O00E 7.1(6) . . . . ? C008 S001 C003 C004 1.3(3) . . . . ? C008 S001 C003 C005 -179.8(3) . . . 3_767 ? C009 C00D C00F O00A 7.2(6) . . . . ? C009 C00D C00F O00E -172.6(4) . . . . ? C00B C006 C00D C009 -0.3(5) . . . . ? C00B C006 C00D C00F -179.9(3) . . . . ? C00B C008 C00C C009 -0.1(5) . . . . ? C00C C008 C00B C006 0.3(5) . . . . ? C00C C009 C00D C006 0.4(5) . . . . ? C00C C009 C00D C00F -179.9(3) . . . . ? C00D C006 C00B C008 -0.1(5) . . . . ? C00D C009 C00C C008 -0.2(5) . . . . ?