#------------------------------------------------------------------------------ #$Date: 2024-08-05 21:12:05 +0300 (Mon, 05 Aug 2024) $ #$Revision: 293776 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/17/1571793.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_1571793 loop_ _publ_author_name 'Zhang, Hongkui' 'Tan, Jian-Ping' 'Ren, Xiaoyu' 'Wang, Fan' 'Zheng, Jia-Yan' 'He, Jiajia' 'Feng, Yu' 'Xu, Zhipeng' 'Su, Zhishan' 'Wang, Tianli' _publ_section_title ; Synergistically activating nucleophile strategy enabled organocatalytic asymmetric P-addition of cyclic imines. ; _journal_issue 30 _journal_name_full 'Chemical science' _journal_page_first 12017 _journal_page_last 12025 _journal_paper_doi 10.1039/d4sc02212b _journal_volume 15 _journal_year 2024 _chemical_absolute_configuration ad _chemical_formula_moiety 'I, C25 H29 F N2 P S' _chemical_formula_sum 'C25 H29 F I N2 P S' _chemical_formula_weight 566.43 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2019-06-21 _audit_creation_method ; Olex2 1.2 (compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155) ; _audit_update_record ; 2019-06-21 deposited with the CCDC. 2024-06-05 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 111.550(5) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.4752(4) _cell_length_b 11.6241(3) _cell_length_c 12.9271(6) _cell_measurement_reflns_used 4293 _cell_measurement_temperature 295.4(6) _cell_measurement_theta_max 71.5140 _cell_measurement_theta_min 3.6980 _cell_volume 1324.27(10) _computing_cell_refinement 'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_environment air _diffrn_ambient_temperature 295.4(6) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 15.9595 _diffrn_detector_type EosS2 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 -53.00 31.00 1.00 1.32 -- -36.04 57.00-150.00 84 2 \w -104.00 -9.00 1.00 1.32 -- -36.04 -77.00 120.00 95 3 \w -105.00 -50.00 1.00 1.32 -- -36.04-159.00 159.00 55 4 \w 1.00 75.00 1.00 1.32 -- 36.04 -99.00-120.00 74 5 \w 23.00 89.00 1.00 1.32 -- 36.04-125.00 90.00 66 6 \w 37.00 109.00 1.00 7.00 -- 106.21 -94.00 -30.00 72 7 \w 36.00 128.00 1.00 7.00 -- 106.21 -30.00-120.00 92 8 \w 85.00 176.00 1.00 7.00 -- 106.21 30.00-150.00 91 9 \w 37.00 109.00 1.00 7.00 -- 106.21 -94.00 -60.00 72 10 \w 36.00 128.00 1.00 7.00 -- 106.21 -30.00 -30.00 92 11 \w 85.00 176.00 1.00 7.00 -- 106.21 30.00 -60.00 91 12 \w 100.00 176.00 1.00 7.00 -- 106.21 111.00 30.00 76 13 \w 36.00 113.00 1.00 7.00 -- 106.21-111.00 120.00 77 14 \w 39.00 133.00 1.00 7.00 -- 106.21 -77.00 120.00 94 15 \w -104.00 -66.00 1.00 1.32 -- -36.04 -77.00-120.00 38 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'New Gemini, Dual, Cu at home/near, EosS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0486373000 _diffrn_orient_matrix_UB_12 -0.0159361000 _diffrn_orient_matrix_UB_13 0.1266660000 _diffrn_orient_matrix_UB_21 -0.1637497000 _diffrn_orient_matrix_UB_22 0.0239375000 _diffrn_orient_matrix_UB_23 -0.0085552000 _diffrn_orient_matrix_UB_31 -0.0364175000 _diffrn_orient_matrix_UB_32 -0.1294282000 _diffrn_orient_matrix_UB_33 -0.0172600000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.1119 _diffrn_reflns_av_unetI/netI 0.0835 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 6569 _diffrn_reflns_point_group_measured_fraction_full 0.731 _diffrn_reflns_point_group_measured_fraction_max 0.731 _diffrn_reflns_theta_full 65.508 _diffrn_reflns_theta_max 65.508 _diffrn_reflns_theta_min 3.676 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 10.974 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.12528 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.421 _exptl_crystal_description plate _exptl_crystal_F_000 572 _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.2 _refine_diff_density_max 2.878 _refine_diff_density_min -2.256 _refine_diff_density_rms 0.266 _refine_ls_abs_structure_details ; Classical Flack method preferred over Parsons because s.u. lower. ; _refine_ls_abs_structure_Flack 0.009(16) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 283 _refine_ls_number_reflns 3343 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.131 _refine_ls_R_factor_all 0.0978 _refine_ls_R_factor_gt 0.0957 _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^)+(0.1668P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2193 _refine_ls_wR_factor_ref 0.2230 _reflns_Friedel_coverage 0.388 _reflns_Friedel_fraction_full 0.432 _reflns_Friedel_fraction_max 0.432 _reflns_number_gt 3172 _reflns_number_total 3343 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc02212b2.cif _cod_data_source_block wtl-zhk-1 _cod_depositor_comments 'Adding full bibliography for 1571793.cif.' _cod_original_cell_volume 1324.26(10) _cod_database_code 1571793 _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 99.92 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _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.a Ternary CH refined with riding coordinates: C6(H6), C25(H25) 2.b Secondary CH2 refined with riding coordinates: C15(H15A,H15B) 2.c Aromatic/amide H refined with riding coordinates: N4(H4), C12(H12), N13(H13), C16(H16), C18(H18), C19(H19), C20(H20), C22(H22), C33(H33), C39(H39), C0AA(H0AA), C11(H11), C9(H9), C1AA(H1AA), C1(H1), C2(H2) 2.d Idealised Me refined as rotating group: C26(H26A,H26B,H26C), C49(H49A,H49B,H49C), C2AA(H2AA,H2AB,H2AC) ; _shelx_res_file ; wtl-zhk-1.res created by SHELXL-2014/7 TITL wtl-zhk-1 in P21 #4 REM reset to P21 #4 CELL 1.54184 9.475153 11.624132 12.927058 90 111.55 90 ZERR 2 0.00038 0.000332 0.000569 0 0.005 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H F I N P S UNIT 50 58 2 2 4 2 2 L.S. 10 PLAN 50 BOND fmap 2 ACTA SHEL 999 0.847 REM REM REM WGHT 0.166800 FVAR 0.62950 I1 4 0.166518 0.827820 0.437740 11.00000 0.04158 0.04469 = 0.03284 -0.01689 0.00359 0.00460 P2 6 -0.356181 0.697610 0.429643 11.00000 0.03688 0.01867 = 0.01661 -0.00114 0.01195 0.00314 S3 7 -0.374370 0.741933 0.033601 11.00000 0.04841 0.05978 = 0.01661 0.00998 0.00084 -0.01629 N4 5 -0.178468 0.714521 0.241799 11.00000 0.04085 0.03145 = 0.01770 0.00149 0.00596 -0.00433 AFIX 43 H4 2 -0.098476 0.737646 0.295267 11.00000 -1.20000 AFIX 0 C6 1 -0.254695 0.615194 0.264361 11.00000 0.03879 0.03125 = 0.00864 0.00305 0.00670 -0.00556 AFIX 13 H6 2 -0.364170 0.623905 0.224128 11.00000 -1.20000 AFIX 0 C7 1 -0.284099 0.715584 0.577829 11.00000 0.05522 0.01975 = 0.02488 0.00131 0.02477 0.00293 C10 1 -0.386581 0.837783 0.366006 11.00000 0.04242 0.01041 = 0.02772 -0.00479 0.01085 0.00162 C12 1 -0.021431 0.968110 0.033810 11.00000 0.03752 0.04339 = 0.04099 0.00471 0.02111 0.00394 AFIX 43 H12 2 0.064289 0.921512 0.059086 11.00000 -1.20000 AFIX 0 N13 5 -0.122204 0.859658 0.150004 11.00000 0.04355 0.06123 = 0.03254 0.02819 0.00724 -0.01139 AFIX 43 H13 2 -0.040340 0.864107 0.208033 11.00000 -1.20000 AFIX 0 C14 1 -0.141088 0.943795 0.066829 11.00000 0.02983 0.03358 = 0.01346 0.00220 0.00554 -0.00674 C15 1 -0.222869 0.612901 0.390532 11.00000 0.04500 0.01496 = 0.01701 0.01135 0.01721 0.01560 AFIX 23 H15A 2 -0.121155 0.641685 0.430256 11.00000 -1.20000 H15B 2 -0.226412 0.533837 0.413456 11.00000 -1.20000 AFIX 0 C16 1 -0.149957 0.665138 0.644481 11.00000 0.05714 0.05119 = 0.01675 0.00554 0.01205 0.01105 AFIX 43 H16 2 -0.095469 0.619552 0.613155 11.00000 -1.20000 AFIX 0 C18 1 -0.277506 1.101432 -0.043515 11.00000 0.03223 0.05868 = 0.05505 0.01966 0.00692 0.00453 AFIX 43 H18 2 -0.363980 1.147021 -0.071237 11.00000 -1.20000 AFIX 0 C19 1 -0.285708 1.023514 0.355532 11.00000 0.07607 0.04349 = 0.10257 0.01339 0.03421 -0.01784 AFIX 43 H19 2 -0.205533 1.075507 0.378669 11.00000 -1.20000 AFIX 0 C20 1 -0.269627 1.013511 0.027395 11.00000 0.03191 0.05303 = 0.03297 0.01793 0.01634 0.00556 AFIX 43 H20 2 -0.350687 0.999613 0.049907 11.00000 -1.20000 AFIX 0 C22 1 -0.269055 0.918273 0.401969 11.00000 0.04682 0.05543 = 0.05640 0.01200 0.00079 -0.01380 AFIX 43 H22 2 -0.178234 0.898927 0.458662 11.00000 -1.20000 AFIX 0 C25 1 -0.203092 0.505343 0.226201 11.00000 0.06099 0.03668 = 0.02451 0.00273 0.02463 0.00722 AFIX 13 H25 2 -0.209049 0.518997 0.149898 11.00000 -1.20000 AFIX 0 C26 1 -0.040639 0.475329 0.293173 11.00000 0.07231 0.05488 = 0.06065 0.00021 0.03155 0.02530 AFIX 137 H26A 2 0.018178 0.544604 0.314181 11.00000 -1.50000 H26B 2 -0.000867 0.428141 0.249298 11.00000 -1.50000 H26C 2 -0.035526 0.434082 0.358793 11.00000 -1.50000 AFIX 0 C33 1 -0.521408 0.868249 0.283099 11.00000 0.05359 0.04953 = 0.07772 0.01981 -0.00290 -0.00459 AFIX 43 H33 2 -0.601933 0.816548 0.260595 11.00000 -1.20000 AFIX 0 C39 1 -0.420812 1.054236 0.274088 11.00000 0.10609 0.02765 = 0.08801 0.02848 0.05175 0.02060 AFIX 43 H39 2 -0.434781 1.128617 0.245600 11.00000 -1.20000 AFIX 0 C42 1 -0.218043 0.773206 0.148648 11.00000 0.03905 0.02659 = 0.01745 0.00452 0.01439 0.00566 C49 1 -0.307088 0.405315 0.221097 11.00000 0.11540 0.03755 = 0.03707 -0.00899 0.03525 -0.01708 AFIX 137 H49A 2 -0.303527 0.387985 0.294625 11.00000 -1.50000 H49B 2 -0.274817 0.339296 0.190969 11.00000 -1.50000 H49C 2 -0.409044 0.425064 0.174454 11.00000 -1.50000 AFIX 0 C0AA 1 -0.537389 0.973076 0.234156 11.00000 0.06413 0.07968 = 0.08539 0.03416 -0.00109 0.02869 AFIX 43 H0AA 2 -0.625503 0.990980 0.174267 11.00000 -1.20000 AFIX 0 C11 1 -0.095604 0.682974 0.760561 11.00000 0.08962 0.03594 = 0.02418 0.00632 0.01101 0.01147 AFIX 43 H11 2 -0.002179 0.653584 0.806225 11.00000 -1.20000 AFIX 0 C2AA 1 -0.530905 0.617734 0.389416 11.00000 0.05056 0.03917 = 0.05105 -0.01655 0.02411 -0.00280 AFIX 137 H2AA 2 -0.509024 0.538306 0.409137 11.00000 -1.50000 H2AB 2 -0.583811 0.624055 0.310505 11.00000 -1.50000 H2AC 2 -0.593055 0.648246 0.427154 11.00000 -1.50000 AFIX 0 C9 1 -0.368395 0.780198 0.625963 11.00000 0.04925 0.05773 = 0.04060 -0.00608 0.02230 0.01064 AFIX 43 H9 2 -0.459611 0.813373 0.580941 11.00000 -1.20000 AFIX 0 C1AA 1 -0.024567 1.058592 -0.034968 11.00000 0.04851 0.05676 = 0.02677 -0.00942 0.02561 -0.00853 AFIX 43 H1AA 2 0.058955 1.075370 -0.053784 11.00000 -1.20000 AFIX 0 C1 1 -0.318263 0.794911 0.737777 11.00000 0.07839 0.05392 = 0.03923 -0.02039 0.04042 0.00463 AFIX 43 H1 2 -0.374669 0.838748 0.768884 11.00000 -1.20000 AFIX 0 C2 1 -0.184891 0.745465 0.805070 11.00000 0.09179 0.05115 = 0.02035 -0.00785 0.03227 -0.00867 AFIX 43 H2 2 -0.153572 0.753844 0.881789 11.00000 -1.20000 AFIX 0 F1 3 -0.159974 1.208826 -0.146430 11.00000 0.09922 0.08488 = 0.06378 0.04869 0.03105 -0.02021 C3AA 1 -0.150902 1.122180 -0.074355 11.00000 0.05796 0.04736 = 0.02885 0.01576 0.01555 -0.00877 HKLF 4 REM wtl-zhk-1 in P21 #4 REM R1 = 0.0957 for 3172 Fo > 4sig(Fo) and 0.0978 for all 3343 data REM 283 parameters refined using 1 restraints END WGHT 0.1669 0.0000 REM Highest difference peak 2.878, deepest hole -2.256, 1-sigma level 0.266 Q1 1 0.1659 0.9160 0.4399 11.00000 0.05 2.88 Q2 1 0.1676 0.7400 0.4348 11.00000 0.05 2.80 Q3 1 0.2133 0.8681 0.5282 11.00000 0.05 1.48 Q4 1 0.2647 0.8249 0.4749 11.00000 0.05 1.33 Q5 1 0.0664 0.8320 0.4051 11.00000 0.05 1.26 Q6 1 -0.3515 0.7846 0.4187 11.00000 0.05 1.09 Q7 1 -0.1537 1.1938 -0.2908 11.00000 0.05 1.03 Q8 1 -0.1770 0.4587 0.4191 11.00000 0.05 0.93 Q9 1 -0.3600 0.6012 0.4255 11.00000 0.05 0.87 Q10 1 0.1636 0.9624 0.2946 11.00000 0.05 0.87 Q11 1 -0.1774 1.2076 0.4049 11.00000 0.05 0.75 Q12 1 -0.3847 0.8282 0.0352 11.00000 0.05 0.74 Q13 1 -0.3322 0.7093 0.1173 11.00000 0.05 0.74 Q14 1 -0.4497 0.8250 0.2788 11.00000 0.05 0.71 Q15 1 -0.3579 0.8825 0.4062 11.00000 0.05 0.70 Q16 1 -0.3386 0.7556 0.4784 11.00000 0.05 0.70 Q17 1 -0.1451 0.6034 0.2352 11.00000 0.05 0.70 Q18 1 0.0239 0.8316 0.3018 11.00000 0.05 0.68 Q19 1 -0.3734 0.6570 0.0344 11.00000 0.05 0.68 Q20 1 -0.3274 0.3408 0.4230 11.00000 0.05 0.67 Q21 1 -0.2214 0.6953 0.1494 11.00000 0.05 0.67 Q22 1 -0.1397 0.4978 0.4847 11.00000 0.05 0.66 Q23 1 -0.3298 1.1961 0.3951 11.00000 0.05 0.66 Q24 1 -0.3532 0.4628 0.3820 11.00000 0.05 0.65 Q25 1 0.1904 0.8802 0.2777 11.00000 0.05 0.65 Q26 1 -0.1196 1.1496 0.4980 11.00000 0.05 0.64 Q27 1 -0.2757 0.4769 0.2357 11.00000 0.05 0.64 Q28 1 -0.1469 0.3893 0.3988 11.00000 0.05 0.64 Q29 1 -0.1414 0.5833 0.6139 11.00000 0.05 0.63 Q30 1 -0.0067 0.9733 0.2470 11.00000 0.05 0.63 Q31 1 -0.1572 0.5057 0.5572 11.00000 0.05 0.62 Q32 1 -0.1418 0.3282 0.2630 11.00000 0.05 0.62 Q33 1 -0.5721 0.8352 0.2216 11.00000 0.05 0.61 Q34 1 -0.1247 0.8247 0.4251 11.00000 0.05 0.61 Q35 1 -0.1913 1.3155 -0.1471 11.00000 0.05 0.60 Q36 1 0.1626 0.6390 0.4288 11.00000 0.05 0.60 Q37 1 -0.1253 0.7447 0.6891 11.00000 0.05 0.58 Q38 1 -0.3087 0.7999 0.6076 11.00000 0.05 0.58 Q39 1 -0.6127 0.9240 0.4531 11.00000 0.05 0.57 Q40 1 -0.1941 1.0188 0.0795 11.00000 0.05 0.57 Q41 1 -0.2071 0.5151 0.6216 11.00000 0.05 0.57 Q42 1 -0.3572 0.8333 0.6721 11.00000 0.05 0.57 Q43 1 -0.2262 0.5775 0.2122 11.00000 0.05 0.56 Q44 1 -0.2549 0.8406 0.3788 11.00000 0.05 0.56 Q45 1 -0.3018 0.6595 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12.81 10 -6 -9 13.61 5.31 -10 6 9 11.77 4.53 10 -6 -8 18.33 7.14 -10 6 8 14.31 5.30 -10 -6 8 5.07 3.02 -10 -6 7 98.29 17.33 10 -6 -7 111.80 16.23 -10 6 7 96.89 11.79 -10 -6 7 59.46 9.04 -10 -6 6 67.68 16.18 10 -6 -6 42.50 10.27 -10 6 6 67.99 9.91 -10 -6 6 37.19 7.13 10 -6 -5 94.11 13.59 -10 6 5 126.94 13.40 -10 -6 5 100.66 11.23 -10 -6 4 44.46 11.89 10 -6 -4 22.10 5.91 -10 6 4 45.64 8.37 -10 -6 4 20.02 4.93 -10 -6 3 89.45 13.95 -10 6 3 33.03 7.12 -10 -6 2 13.66 5.19 -10 6 2 7.83 4.15 10 -6 -2 10.03 5.12 -10 6 1 4.47 2.99 10 -6 -1 2.51 3.08 10 -7 -7 5.90 4.81 -10 7 7 5.67 3.94 -10 -7 6 1.83 5.58 10 -7 -6 -1.22 3.57 -10 7 6 2.69 2.98 -10 -7 5 16.58 8.30 -10 7 5 17.88 5.45 -10 -7 4 150.98 19.32 -10 7 4 93.69 11.24 -10 -7 3 75.52 12.02 10 -7 -3 40.02 9.12 11 0 -10 65.93 9.11 11 0 -9 60.06 11.03 -11 0 9 19.48 5.63 11 0 -8 43.48 10.94 -11 0 8 15.13 5.39 11 0 -7 1.65 4.26 -11 0 7 -0.02 3.43 11 0 -6 6.81 5.08 -11 0 6 9.92 4.74 11 0 -5 10.21 4.53 -11 0 5 14.27 5.71 -11 0 4 77.10 10.85 -11 0 3 56.89 8.25 -11 0 3 54.94 9.05 -11 0 2 81.39 10.23 11 -1 -10 7.42 3.54 11 1 -10 12.65 4.57 11 -1 -9 17.75 6.64 11 1 -9 21.86 7.32 -11 -1 9 7.08 3.93 11 -1 -8 34.66 9.87 11 1 -8 25.79 8.84 -11 1 8 6.39 3.99 -11 -1 8 13.70 5.37 11 -1 -7 92.14 14.78 -11 1 7 76.17 11.41 -11 -1 7 64.91 9.88 11 -1 -6 34.34 8.72 11 1 -6 27.71 8.39 -11 1 6 27.48 7.51 -11 -1 6 30.26 7.09 11 -1 -5 112.06 12.84 11 1 -5 97.38 11.89 -11 1 5 155.65 16.19 -11 -1 5 164.67 15.02 -11 -1 4 50.66 9.61 -11 1 4 37.46 8.09 -11 -1 4 39.90 7.63 -11 -1 3 4.07 2.77 -11 1 3 6.87 4.35 -11 -1 3 3.70 3.22 -11 -1 2 2.65 2.52 -11 -2 9 4.26 4.56 11 -2 -9 3.69 3.75 -11 -2 9 4.98 3.81 11 -2 -8 109.57 15.16 -11 -2 8 61.33 9.21 11 -2 -7 2.69 4.65 -11 -2 7 -0.86 3.34 11 -2 -6 8.39 4.68 -11 -2 6 7.92 4.13 -11 -2 5 44.56 10.64 11 -2 -5 16.12 4.86 -11 2 5 52.19 9.65 -11 2 5 47.92 9.55 -11 -2 5 26.72 6.46 -11 -2 4 51.95 9.89 -11 2 4 49.22 9.18 -11 2 4 48.26 9.52 -11 -2 4 32.73 6.85 -11 -2 3 84.24 10.44 -11 2 3 83.70 11.42 -11 -2 3 75.58 9.89 -11 -2 2 37.23 6.72 11 -3 -9 13.25 4.85 -11 -3 9 9.16 3.90 -11 -3 8 73.67 13.55 -11 -3 8 48.64 8.02 11 -3 -7 45.93 9.66 -11 3 7 37.74 7.80 -11 -3 7 42.64 7.78 11 -3 -6 55.48 9.93 -11 3 6 82.17 11.33 -11 -3 6 64.14 9.45 11 -3 -5 37.09 7.11 -11 3 5 39.22 8.48 -11 -3 5 53.65 8.51 -11 -3 4 20.90 6.63 -11 3 4 27.87 7.04 -11 -3 4 15.07 4.77 -11 -3 3 14.86 4.80 -11 3 3 10.31 4.95 -11 -3 3 7.89 3.58 11 -4 -8 7.37 4.94 -11 -4 8 -0.29 2.79 -11 -4 7 14.05 6.99 11 -4 -7 9.10 4.70 -11 -4 7 7.71 3.81 11 -4 -6 29.76 7.08 -11 4 6 26.07 6.43 -11 -4 6 23.56 5.53 -11 4 5 37.98 7.72 -11 -4 5 32.03 6.40 -11 4 4 62.21 9.38 -11 -4 4 50.09 7.64 TITL wtl-zhk-1 in P2(1)/m REM P2(1)/m (#11 in standard setting) CELL 1.54184 9.475153 11.624132 12.927058 90.0000 111.5500 90.0000 ZERR 11.00 0.000380 0.000332 0.000569 0.0000 0.0050 0.0000 LATT 1 SYMM -x, y+1/2,-z SFAC C H N O UNIT 121.00 110.00 11.00 11.00 TREF HKLF 4 END _computing_structure_solution 'SHELXT 2014/4 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT 2014/4 (Sheldrick, 2014)' ; _shelx_hkl_checksum 77167 _shelx_shelxl_version_number 2014/7 _olex2_date_sample_data_collection 2019-06-21 _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 4.343 _oxdiff_exptl_absorpt_empirical_full_min 0.312 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' 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 I1 I 0.16652(8) 0.82782(9) 0.43774(6) 0.0426(4) Uani 1 1 d . . . . . P2 P -0.3562(4) 0.6976(3) 0.4296(2) 0.0235(7) Uani 1 1 d . . . . . S3 S -0.3744(4) 0.7419(4) 0.0336(3) 0.0447(10) Uani 1 1 d . . . . . N4 N -0.1785(13) 0.7145(11) 0.2418(9) 0.031(2) Uani 1 1 d . . . . . H4 H -0.0985 0.7376 0.2953 0.038 Uiso 1 1 calc R . . . . C6 C -0.2547(14) 0.6152(12) 0.2644(9) 0.027(3) Uani 1 1 d . . . . . H6 H -0.3642 0.6239 0.2241 0.032 Uiso 1 1 calc R . . . . C7 C -0.2841(17) 0.7156(12) 0.5778(11) 0.030(3) Uani 1 1 d . . . . . C10 C -0.3866(14) 0.8378(12) 0.3660(10) 0.027(2) Uani 1 1 d . . . . . C12 C -0.0214(17) 0.9681(15) 0.0338(13) 0.039(3) Uani 1 1 d . . . . . H12 H 0.0643 0.9215 0.0591 0.046 Uiso 1 1 calc R . . . . N13 N -0.1222(15) 0.8597(13) 0.1500(11) 0.048(4) Uani 1 1 d . . . . . H13 H -0.0403 0.8641 0.2080 0.057 Uiso 1 1 calc R . . . . C14 C -0.1411(14) 0.9438(14) 0.0668(9) 0.026(3) Uani 1 1 d . . . . . C15 C -0.2229(15) 0.6129(11) 0.3905(9) 0.024(3) Uani 1 1 d . . . . . H15A H -0.1212 0.6417 0.4303 0.029 Uiso 1 1 calc R . . . . H15B H -0.2264 0.5338 0.4135 0.029 Uiso 1 1 calc R . . . . C16 C -0.1500(19) 0.6651(16) 0.6445(11) 0.042(4) Uani 1 1 d . . . . . H16 H -0.0955 0.6196 0.6132 0.051 Uiso 1 1 calc R . . . . C18 C -0.2775(17) 1.1014(17) -0.0435(16) 0.051(4) Uani 1 1 d . . . . . H18 H -0.3640 1.1470 -0.0712 0.061 Uiso 1 1 calc R . . . . C19 C -0.286(3) 1.0235(19) 0.356(3) 0.074(7) Uani 1 1 d . . . . . H19 H -0.2055 1.0755 0.3787 0.088 Uiso 1 1 calc R . . . . C20 C -0.2696(15) 1.0135(15) 0.0274(12) 0.038(3) Uani 1 1 d . . . . . H20 H -0.3507 0.9996 0.0499 0.046 Uiso 1 1 calc R . . . . C22 C -0.269(2) 0.918(2) 0.4020(17) 0.058(5) Uani 1 1 d . . . . . H22 H -0.1782 0.8989 0.4587 0.070 Uiso 1 1 calc R . . . . C25 C -0.2031(18) 0.5053(14) 0.2262(12) 0.038(3) Uani 1 1 d . . . . . H25 H -0.2090 0.5190 0.1499 0.046 Uiso 1 1 calc R . . . . C26 C -0.041(2) 0.4753(19) 0.2932(18) 0.061(5) Uani 1 1 d . . . . . H26A H 0.0182 0.5446 0.3142 0.091 Uiso 1 1 calc GR . . . . H26B H -0.0009 0.4281 0.2493 0.091 Uiso 1 1 calc GR . . . . H26C H -0.0355 0.4341 0.3588 0.091 Uiso 1 1 calc GR . . . . C33 C -0.521(2) 0.8682(19) 0.283(2) 0.068(6) Uani 1 1 d . . . . . H33 H -0.6019 0.8165 0.2606 0.082 Uiso 1 1 calc R . . . . C39 C -0.421(3) 1.0542(16) 0.274(2) 0.069(6) Uani 1 1 d . . . . . H39 H -0.4348 1.1286 0.2456 0.083 Uiso 1 1 calc R . . . . C42 C -0.2180(15) 0.7732(12) 0.1486(10) 0.027(2) Uani 1 1 d . . . . . C49 C -0.307(3) 0.4053(18) 0.2211(15) 0.061(5) Uani 1 1 d . . . . . H49A H -0.3035 0.3880 0.2946 0.092 Uiso 1 1 calc GR . . . . H49B H -0.2748 0.3393 0.1910 0.092 Uiso 1 1 calc GR . . . . H49C H -0.4090 0.4251 0.1745 0.092 Uiso 1 1 calc GR . . . . C0AA C -0.537(3) 0.973(2) 0.234(2) 0.084(8) Uani 1 1 d . . . . . H0AA H -0.6255 0.9910 0.1743 0.101 Uiso 1 1 calc R . . . . C11 C -0.096(3) 0.6830(16) 0.7606(13) 0.053(4) Uani 1 1 d . . . . . H11 H -0.0022 0.6536 0.8062 0.063 Uiso 1 1 calc R . . . . C2AA C -0.5309(18) 0.6177(15) 0.3894(15) 0.045(4) Uani 1 1 d . . . . . H2AA H -0.5090 0.5383 0.4091 0.068 Uiso 1 1 calc GR . . . . H2AB H -0.5838 0.6241 0.3105 0.068 Uiso 1 1 calc GR . . . . H2AC H -0.5931 0.6482 0.4272 0.068 Uiso 1 1 calc GR . . . . C9 C -0.3684(19) 0.7802(16) 0.6260(14) 0.048(4) Uani 1 1 d . . . . . H9 H -0.4596 0.8134 0.5809 0.057 Uiso 1 1 calc R . . . . C1AA C -0.0246(17) 1.0586(15) -0.0350(11) 0.041(4) Uani 1 1 d . . . . . H1AA H 0.0590 1.0754 -0.0538 0.049 Uiso 1 1 calc R . . . . C1 C -0.318(2) 0.7949(16) 0.7378(14) 0.052(5) Uani 1 1 d . . . . . H1 H -0.3747 0.8387 0.7689 0.062 Uiso 1 1 calc R . . . . C2 C -0.185(2) 0.7455(17) 0.8051(12) 0.051(4) Uani 1 1 d . . . . . H2 H -0.1536 0.7538 0.8818 0.061 Uiso 1 1 calc R . . . . F1 F -0.1600(17) 1.2088(13) -0.1464(11) 0.082(4) Uani 1 1 d . . . . . C3AA C -0.1509(19) 1.1222(16) -0.0744(13) 0.045(4) 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 I1 0.0416(5) 0.0447(6) 0.0328(5) -0.0169(4) 0.0036(3) 0.0046(4) P2 0.0369(14) 0.0187(17) 0.0166(14) -0.0011(11) 0.0119(11) 0.0031(12) S3 0.0484(18) 0.060(2) 0.0166(14) 0.0100(15) 0.0008(13) -0.0163(17) N4 0.041(5) 0.031(6) 0.018(5) 0.001(4) 0.006(4) -0.004(5) C6 0.039(6) 0.031(7) 0.009(5) 0.003(5) 0.007(4) -0.006(5) C7 0.055(7) 0.020(6) 0.025(6) 0.001(5) 0.025(6) 0.003(5) C10 0.042(5) 0.010(6) 0.028(5) -0.005(5) 0.011(4) 0.002(5) C12 0.038(7) 0.043(9) 0.041(7) 0.005(7) 0.021(6) 0.004(6) N13 0.044(6) 0.061(10) 0.033(6) 0.028(6) 0.007(5) -0.011(6) C14 0.030(5) 0.034(8) 0.013(5) 0.002(5) 0.006(4) -0.007(5) C15 0.045(7) 0.015(6) 0.017(5) 0.011(5) 0.017(5) 0.016(5) C16 0.057(8) 0.051(10) 0.017(6) 0.006(6) 0.012(6) 0.011(7) C18 0.032(7) 0.059(12) 0.055(9) 0.020(9) 0.007(7) 0.005(7) C19 0.076(14) 0.043(12) 0.103(19) 0.013(12) 0.034(13) -0.018(10) C20 0.032(6) 0.053(10) 0.033(7) 0.018(7) 0.016(5) 0.006(6) C22 0.047(8) 0.055(11) 0.056(10) 0.012(9) 0.001(8) -0.014(8) C25 0.061(8) 0.037(8) 0.025(6) 0.003(6) 0.025(6) 0.007(7) C26 0.072(12) 0.055(12) 0.061(11) 0.000(10) 0.032(10) 0.025(10) C33 0.054(9) 0.050(11) 0.078(13) 0.020(10) -0.003(9) -0.005(8) C39 0.106(17) 0.028(10) 0.088(15) 0.028(10) 0.052(13) 0.021(10) C42 0.039(6) 0.027(6) 0.017(5) 0.005(5) 0.014(5) 0.006(5) C49 0.115(16) 0.038(9) 0.037(8) -0.009(8) 0.035(10) -0.017(10) C0AA 0.064(12) 0.080(18) 0.085(16) 0.034(15) -0.001(11) 0.029(12) C11 0.090(12) 0.036(9) 0.024(7) 0.006(7) 0.011(8) 0.011(9) C2AA 0.051(8) 0.039(9) 0.051(9) -0.017(8) 0.024(7) -0.003(7) C9 0.049(8) 0.058(10) 0.041(8) -0.006(7) 0.022(7) 0.011(7) C1AA 0.049(8) 0.057(11) 0.027(6) -0.009(7) 0.026(6) -0.009(7) C1 0.078(11) 0.054(12) 0.039(8) -0.020(8) 0.040(8) 0.005(8) C2 0.092(12) 0.051(10) 0.020(6) -0.008(7) 0.032(8) -0.009(9) F1 0.099(9) 0.085(10) 0.064(7) 0.049(7) 0.031(7) -0.020(8) C3AA 0.058(9) 0.047(10) 0.029(7) 0.016(7) 0.016(6) -0.009(8) 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' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.3257 6.8362 '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' P P 0.2955 0.4335 '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 C7 P2 C10 108.5(6) . . ? C7 P2 C15 109.3(6) . . ? C7 P2 C2AA 108.5(8) . . ? C10 P2 C15 112.0(6) . . ? C10 P2 C2AA 111.0(8) . . ? C2AA P2 C15 107.5(7) . . ? C42 N4 C6 127.1(11) . . ? N4 C6 C15 107.9(10) . . ? N4 C6 C25 111.3(11) . . ? C25 C6 C15 111.6(11) . . ? C16 C7 P2 121.3(10) . . ? C16 C7 C9 119.8(13) . . ? C9 C7 P2 118.8(12) . . ? C22 C10 P2 118.7(12) . . ? C33 C10 P2 122.3(12) . . ? C33 C10 C22 119.0(16) . . ? C1AA C12 C14 122.2(14) . . ? C42 N13 C14 127.4(12) . . ? C12 C14 N13 119.2(13) . . ? C12 C14 C20 118.3(13) . . ? C20 C14 N13 121.9(12) . . ? C6 C15 P2 113.5(8) . . ? C7 C16 C11 119.7(15) . . ? C20 C18 C3AA 118.4(15) . . ? C22 C19 C39 120(2) . . ? C18 C20 C14 120.6(13) . . ? C19 C22 C10 120.8(18) . . ? C26 C25 C6 113.1(14) . . ? C26 C25 C49 111.1(17) . . ? C49 C25 C6 112.3(14) . . ? C0AA C33 C10 120(2) . . ? C19 C39 C0AA 119.7(18) . . ? N4 C42 S3 123.5(11) . . ? N4 C42 N13 114.2(12) . . ? N13 C42 S3 122.2(10) . . ? C33 C0AA C39 120(2) . . ? C2 C11 C16 118.5(17) . . ? C1 C9 C7 120.6(16) . . ? C3AA C1AA C12 118.3(13) . . ? C9 C1 C2 120.3(14) . . ? C1 C2 C11 121.1(14) . . ? C1AA C3AA C18 122.0(15) . . ? C1AA C3AA F1 119.7(15) . . ? F1 C3AA C18 118.3(16) . . ? 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 P2 C7 1.794(13) . ? P2 C10 1.800(14) . ? P2 C15 1.814(12) . ? P2 C2AA 1.800(17) . ? S3 C42 1.709(13) . ? N4 C6 1.447(18) . ? N4 C42 1.313(17) . ? C6 C15 1.546(14) . ? C6 C25 1.51(2) . ? C7 C16 1.38(2) . ? C7 C9 1.40(2) . ? C10 C22 1.40(2) . ? C10 C33 1.38(2) . ? C12 C14 1.379(19) . ? C12 C1AA 1.37(2) . ? N13 C14 1.415(19) . ? N13 C42 1.350(19) . ? C14 C20 1.39(2) . ? C16 C11 1.41(2) . ? C18 C20 1.36(2) . ? C18 C3AA 1.42(2) . ? C19 C22 1.35(3) . ? C19 C39 1.37(4) . ? C25 C26 1.50(2) . ? C25 C49 1.51(3) . ? C33 C0AA 1.36(3) . ? C39 C0AA 1.40(4) . ? C11 C2 1.39(3) . ? C9 C1 1.36(2) . ? C1AA C3AA 1.34(3) . ? C1 C2 1.37(3) . ? F1 C3AA 1.353(19) . ?