#------------------------------------------------------------------------------ #$Date: 2017-11-21 08:42:36 +0200 (Tue, 21 Nov 2017) $ #$Revision: 203411 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/96/7229603.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_7229603 loop_ _publ_author_name 'Le Phuong, Hai Anh' 'Cseri, Levente' 'Whitehead, George F. S.' 'Garforth, Arthur' 'Budd, Peter' 'Szekely, Gyorgy' _publ_section_title ; Environmentally benign and diastereoselective synthesis of 2,4,5-trisubstituted-2-imidazolines ; _journal_issue 84 _journal_name_full 'RSC Advances' _journal_page_first 53278 _journal_paper_doi 10.1039/C7RA11827A _journal_volume 7 _journal_year 2017 _chemical_formula_moiety 'C21 H15 F15 N2 S3' _chemical_formula_sum 'C21 H15 F15 N2 S3' _chemical_formula_weight 676.53 _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' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary iterative _audit_creation_date 2017-08-17 _audit_creation_method ; Olex2 1.2 (compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375) ; _audit_update_record ; 2017-09-22 deposited with the CCDC. 2017-11-13 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 91.4162(15) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.2146(2) _cell_length_b 9.99845(16) _cell_length_c 20.3665(3) _cell_measurement_reflns_used 14317 _cell_measurement_temperature 150.01(10) _cell_measurement_theta_max 26.3450 _cell_measurement_theta_min 1.9050 _cell_volume 2486.54(7) _computing_cell_refinement 'CrysAlisPro 1.171.39.21a (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.39.21a (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.39.21a (Rigaku OD, 2015)' _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 ; Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012) ; _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 150.01(10) _diffrn_detector 'CCD plate' _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 -71.00 7.00 1.00 1.00 -- 17.60 29.00 -4.00 78 2 \w -71.00 27.00 1.00 1.00 -- 17.60 43.00-180.00 98 3 \w -59.00 -33.00 1.00 1.00 -- 17.60 60.00-120.00 26 4 \w -17.00 107.00 1.00 1.00 -- 17.60 60.00-120.00 124 5 \w -72.00 107.00 1.00 1.00 -- 17.60 14.00 120.00 179 6 \w 17.00 97.00 1.00 1.00 -- 17.60 60.00-150.00 80 7 \w 72.00 98.00 1.00 1.00 -- 17.60 29.00 -4.00 26 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB AFC11 (RINC): quarter-chi single' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0060308000 _diffrn_orient_matrix_UB_12 -0.0028886000 _diffrn_orient_matrix_UB_13 0.0345242000 _diffrn_orient_matrix_UB_21 -0.0505895000 _diffrn_orient_matrix_UB_22 -0.0339661000 _diffrn_orient_matrix_UB_23 -0.0046092000 _diffrn_orient_matrix_UB_31 0.0278971000 _diffrn_orient_matrix_UB_32 -0.0622056000 _diffrn_orient_matrix_UB_33 0.0009198000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_unetI/netI 0.0169 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 27722 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.372 _diffrn_reflns_theta_min 2.269 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.428 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.73995 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.21a (Rigaku Oxford Diffraction, 2015) 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 1.807 _exptl_crystal_description block _exptl_crystal_F_000 1352 _exptl_crystal_size_max 0.402 _exptl_crystal_size_mid 0.375 _exptl_crystal_size_min 0.209 _refine_diff_density_max 0.373 _refine_diff_density_min -0.716 _refine_diff_density_rms 0.053 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 430 _refine_ls_number_reflns 5087 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.054 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0373 _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^)+(0.0404P)^2^+2.2032P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0929 _refine_ls_wR_factor_ref 0.0963 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4490 _reflns_number_total 5087 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ra11827a2.cif _cod_data_source_block s4866l _cod_database_code 7229603 _shelx_shelxl_version_number 2016/6 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.916 _shelx_estimated_absorpt_t_min 0.847 _reflns_odcompleteness_completeness 99.83 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; ; _shelx_res_file ; TITL s4866l in P2(1)/c s4866l.res created by SHELXL-2016/6 at 10:11:38 on 17-Aug-2017 CELL 0.71073 12.214561 9.998454 20.366543 90 91.4162 90 ZERR 4 0.000201 0.000158 0.000337 0 0.0015 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H F N S UNIT 84 60 60 8 12 L.S. 4 PLAN 20 SIZE 0.209 0.375 0.402 fmap 2 53 acta REM REM REM WGHT 0.040400 2.203200 FVAR 3.27130 S1 5 1.493168 0.507315 0.190540 11.00000 0.02224 0.03143 = 0.04265 0.00730 0.00417 0.00054 S3 5 0.812422 0.118566 0.534058 11.00000 0.04141 0.04368 = 0.02834 0.01123 0.00027 -0.01395 S2 5 0.678511 0.651161 0.563645 11.00000 0.13036 0.03158 = 0.04850 0.00609 0.05512 0.01838 F2 3 1.619942 0.502585 0.176299 11.00000 0.02160 0.05793 = 0.06844 0.00711 0.00769 0.00113 F1 3 1.488128 0.353515 0.171325 11.00000 0.03079 0.03326 = 0.06246 -0.00132 0.00663 0.00718 F5 3 1.472906 0.546158 0.116328 11.00000 0.03040 0.06127 = 0.04351 0.01884 0.01297 0.00377 F4 3 1.524278 0.466017 0.264069 11.00000 0.03182 0.05738 = 0.04708 0.01192 -0.00718 0.00135 F13 3 0.704257 0.044946 0.512033 11.00000 0.04119 0.04647 = 0.04447 0.01684 0.00173 -0.01758 F11 3 0.921208 0.184367 0.561952 11.00000 0.08340 0.12905 = 0.04076 0.03777 -0.02688 -0.06784 F12 3 0.804116 0.044298 0.602223 11.00000 0.06391 0.08182 = 0.03641 0.02906 -0.00126 -0.02432 F3 3 1.509507 0.659739 0.209380 11.00000 0.03236 0.03382 = 0.07853 0.00139 0.00986 -0.00964 F9 3 0.600025 0.768553 0.544634 11.00000 0.14176 0.06303 = 0.07554 0.01033 0.07084 0.04739 F15 3 0.880753 -0.005449 0.509049 11.00000 0.05753 0.06185 = 0.06797 0.04146 0.01753 0.02050 F10 3 0.755249 0.535130 0.588945 11.00000 0.20438 0.06108 = 0.04301 0.01992 0.05373 0.05700 F14 3 0.742337 0.235265 0.563543 11.00000 0.12176 0.04960 = 0.04003 -0.00192 0.03620 -0.00439 N2 4 0.950087 0.403684 0.240051 11.00000 0.02463 0.01720 = 0.02506 -0.00131 0.00567 0.00023 F8 3 0.585237 0.545966 0.548221 11.00000 0.15066 0.07442 = 0.10517 -0.00126 0.09697 -0.02991 F6 3 0.769643 0.757218 0.584931 11.00000 0.16932 0.06217 = 0.04225 -0.01970 0.02775 0.00009 F7 3 0.634028 0.660717 0.635681 11.00000 0.22539 0.06350 = 0.06297 0.01388 0.09487 0.04259 N1 4 0.965521 0.614350 0.280347 11.00000 0.02687 0.01728 = 0.02775 0.00136 0.00851 -0.00184 C1 1 1.349241 0.512793 0.207651 11.00000 0.02104 0.02136 = 0.03141 0.00755 0.00350 0.00012 C7 1 1.012581 0.514120 0.252832 11.00000 0.02605 0.01889 = 0.01853 0.00302 0.00247 -0.00057 C19 1 0.823890 0.203090 0.456189 11.00000 0.03241 0.02203 = 0.02347 0.00299 0.00162 -0.00602 C16 1 0.841780 0.333786 0.336437 11.00000 0.02385 0.01410 = 0.02278 -0.00211 0.00170 -0.00154 C15 1 0.847678 0.417848 0.274794 11.00000 0.02174 0.01871 = 0.02337 -0.00087 0.00154 0.00043 C9 1 0.809549 0.608848 0.356406 11.00000 0.02669 0.01334 = 0.02944 0.00014 0.00626 -0.00045 C3 1 1.204553 0.581247 0.276792 11.00000 0.03078 0.02468 = 0.02370 0.00014 0.00357 -0.00125 C17 1 0.739602 0.312185 0.363966 11.00000 0.02212 0.01748 = 0.02983 -0.00084 0.00092 -0.00064 C14 1 0.698719 0.628808 0.365682 11.00000 0.02888 0.02111 = 0.03995 0.00035 0.00739 0.00132 C8 1 0.850456 0.574540 0.289340 11.00000 0.02448 0.01703 = 0.02530 0.00199 0.00261 0.00161 C6 1 1.275295 0.451403 0.164812 11.00000 0.02842 0.02065 = 0.02856 0.00132 0.00671 0.00259 C18 1 0.729924 0.249412 0.424092 11.00000 0.02478 0.02131 = 0.03070 -0.00106 0.00600 -0.00413 C21 1 0.934301 0.285091 0.369463 11.00000 0.02127 0.02119 = 0.02792 0.00098 0.00279 -0.00141 C4 1 1.129474 0.515623 0.235470 11.00000 0.02522 0.01664 = 0.02383 0.00427 0.00431 0.00072 C20 1 0.925840 0.218411 0.428946 11.00000 0.02526 0.02608 = 0.03071 0.00521 -0.00289 -0.00129 C2 1 1.315143 0.579287 0.263574 11.00000 0.02890 0.02766 = 0.02924 0.00206 -0.00091 -0.00301 C12 1 0.729799 0.638692 0.481770 11.00000 0.06547 0.01871 = 0.03475 -0.00009 0.02670 0.00287 C5 1 1.165119 0.451109 0.179441 11.00000 0.02467 0.02031 = 0.02687 -0.00081 0.00327 -0.00139 C10 1 0.880658 0.608573 0.410827 11.00000 0.03252 0.02416 = 0.03147 -0.00345 0.00374 -0.00240 C13 1 0.658009 0.643331 0.428238 11.00000 0.03975 0.02387 = 0.05542 0.00277 0.02577 0.00505 C11 1 0.840625 0.623088 0.473573 11.00000 0.05720 0.02852 = 0.02755 -0.00493 0.00403 -0.00146 H8 2 0.804524 0.618855 0.256048 11.00000 0.02096 H6 2 1.297597 0.409628 0.126213 11.00000 0.02363 H15 2 0.785647 0.395530 0.246601 11.00000 0.01979 H5 2 1.114455 0.407944 0.149519 11.00000 0.01909 H18 2 0.661435 0.237452 0.442342 11.00000 0.03156 H17 2 0.674378 0.341495 0.340839 11.00000 0.03123 H3 2 1.179095 0.625637 0.315879 11.00000 0.02637 H2 2 0.977011 0.325909 0.233233 11.00000 0.02616 H21 2 1.003917 0.293433 0.350518 11.00000 0.03105 H10 2 0.958587 0.596661 0.404959 11.00000 0.03715 H20 2 0.987514 0.186442 0.450703 11.00000 0.03365 H2A 2 1.367852 0.621105 0.294492 11.00000 0.03850 H13 2 0.586329 0.656320 0.432842 11.00000 0.05684 H14 2 0.648871 0.629373 0.328865 11.00000 0.03098 H11 2 0.890412 0.622311 0.510376 11.00000 0.05116 HKLF 4 REM s4866l in P2(1)/c REM R1 = 0.0373 for 4490 Fo > 4sig(Fo) and 0.0426 for all 5087 data REM 430 parameters refined using 0 restraints END WGHT 0.0404 2.2034 REM Highest difference peak 0.373, deepest hole -0.716, 1-sigma level 0.053 Q1 1 1.4147 0.5161 0.2012 11.00000 0.05 0.37 Q2 1 0.7058 0.7670 0.5778 11.00000 0.05 0.35 Q3 1 0.9023 0.0584 0.5346 11.00000 0.05 0.34 Q4 1 0.8721 0.2572 0.5626 11.00000 0.05 0.32 Q5 1 0.6272 0.6833 0.5451 11.00000 0.05 0.29 Q6 1 0.6688 0.6766 0.6445 11.00000 0.05 0.28 Q7 1 0.9446 0.1612 0.5580 11.00000 0.05 0.27 Q8 1 0.7959 0.7927 0.5961 11.00000 0.05 0.27 Q9 1 0.5467 0.7161 0.5264 11.00000 0.05 0.27 Q10 1 0.8164 0.1626 0.4885 11.00000 0.05 0.27 Q11 1 1.0715 0.5154 0.2414 11.00000 0.05 0.26 Q12 1 0.8465 0.4992 0.2801 11.00000 0.05 0.26 Q13 1 0.7810 0.6969 0.6016 11.00000 0.05 0.26 Q14 1 0.8991 0.4037 0.2582 11.00000 0.05 0.24 Q15 1 0.8455 0.3662 0.3033 11.00000 0.05 0.24 Q16 1 0.7045 0.6441 0.5184 11.00000 0.05 0.24 Q17 1 0.9071 0.5982 0.2843 11.00000 0.05 0.23 Q18 1 0.8913 -0.0287 0.4936 11.00000 0.05 0.22 Q19 1 0.8307 0.5879 0.3237 11.00000 0.05 0.22 Q20 1 0.5831 0.6299 0.6211 11.00000 0.05 0.20 ; _shelx_res_checksum 18744 _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 1.333 _oxdiff_exptl_absorpt_empirical_full_min 0.619 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 S1 S 1.49317(4) 0.50732(5) 0.19054(3) 0.03205(13) Uani 1 1 d S3 S 0.81242(5) 0.11857(6) 0.53406(3) 0.03782(14) Uani 1 1 d S2 S 0.67851(8) 0.65116(6) 0.56365(3) 0.0693(3) Uani 1 1 d F2 F 1.61994(10) 0.50259(15) 0.17630(8) 0.0492(4) Uani 1 1 d F1 F 1.48813(10) 0.35352(12) 0.17132(7) 0.0421(3) Uani 1 1 d F5 F 1.47291(10) 0.54616(15) 0.11633(7) 0.0449(3) Uani 1 1 d F4 F 1.52428(10) 0.46602(14) 0.26407(7) 0.0456(3) Uani 1 1 d F13 F 0.70426(10) 0.04495(14) 0.51203(6) 0.0440(3) Uani 1 1 d F11 F 0.92121(15) 0.1844(2) 0.56195(8) 0.0849(7) Uani 1 1 d F12 F 0.80412(13) 0.04430(18) 0.60222(7) 0.0608(4) Uani 1 1 d F3 F 1.50951(10) 0.65974(13) 0.20938(8) 0.0481(3) Uani 1 1 d F9 F 0.60002(19) 0.76855(18) 0.54463(9) 0.0923(7) Uani 1 1 d F15 F 0.88075(13) -0.00545(16) 0.50905(8) 0.0622(5) Uani 1 1 d F10 F 0.7552(2) 0.53513(19) 0.58894(8) 0.1020(9) Uani 1 1 d F14 F 0.74234(17) 0.23526(16) 0.56354(7) 0.0699(5) Uani 1 1 d N2 N 0.95009(12) 0.40368(15) 0.24005(7) 0.0222(3) Uani 1 1 d F8 F 0.5852(2) 0.5460(2) 0.54822(12) 0.1085(9) Uani 1 1 d F6 F 0.7696(2) 0.75722(19) 0.58493(8) 0.0908(7) Uani 1 1 d F7 F 0.6340(2) 0.66072(19) 0.63568(9) 0.1158(10) Uani 1 1 d N1 N 0.96552(12) 0.61435(14) 0.28035(8) 0.0238(3) Uani 1 1 d C1 C 1.34924(14) 0.51279(18) 0.20765(9) 0.0246(4) Uani 1 1 d C7 C 1.01258(14) 0.51412(17) 0.25283(8) 0.0211(3) Uani 1 1 d C19 C 0.82389(15) 0.20309(18) 0.45619(9) 0.0260(4) Uani 1 1 d C16 C 0.84178(14) 0.33379(16) 0.33644(8) 0.0202(3) Uani 1 1 d C15 C 0.84768(14) 0.41785(17) 0.27479(9) 0.0213(3) Uani 1 1 d C9 C 0.80955(14) 0.60885(16) 0.35641(9) 0.0231(4) Uani 1 1 d C3 C 1.20455(16) 0.58125(19) 0.27679(9) 0.0263(4) Uani 1 1 d C17 C 0.73960(14) 0.31218(17) 0.36397(9) 0.0231(4) Uani 1 1 d C14 C 0.69872(16) 0.62881(19) 0.36568(11) 0.0299(4) Uani 1 1 d C8 C 0.85046(14) 0.57454(17) 0.28934(9) 0.0222(4) Uani 1 1 d C6 C 1.27530(15) 0.45140(18) 0.16481(10) 0.0258(4) Uani 1 1 d C18 C 0.72992(15) 0.24941(18) 0.42409(10) 0.0255(4) Uani 1 1 d C21 C 0.93430(14) 0.28509(18) 0.36946(9) 0.0234(4) Uani 1 1 d C4 C 1.12947(14) 0.51562(17) 0.23547(9) 0.0218(4) Uani 1 1 d C20 C 0.92584(15) 0.21841(19) 0.42895(10) 0.0274(4) Uani 1 1 d C2 C 1.31514(16) 0.57929(19) 0.26357(10) 0.0286(4) Uani 1 1 d C12 C 0.7298(2) 0.63869(19) 0.48177(11) 0.0392(5) Uani 1 1 d C5 C 1.16512(15) 0.45111(18) 0.17944(9) 0.0239(4) Uani 1 1 d C10 C 0.88066(17) 0.60857(19) 0.41083(10) 0.0293(4) Uani 1 1 d C13 C 0.65801(19) 0.6433(2) 0.42824(12) 0.0393(5) Uani 1 1 d C11 C 0.8406(2) 0.6231(2) 0.47357(11) 0.0377(5) Uani 1 1 d H8 H 0.8045(16) 0.619(2) 0.2560(10) 0.021(5) Uiso 1 1 d H6 H 1.2976(16) 0.410(2) 0.1262(11) 0.024(5) Uiso 1 1 d H15 H 0.7856(16) 0.396(2) 0.2466(10) 0.020(5) Uiso 1 1 d H5 H 1.1145(16) 0.408(2) 0.1495(10) 0.019(5) Uiso 1 1 d H18 H 0.6614(18) 0.237(2) 0.4423(11) 0.032(6) Uiso 1 1 d H17 H 0.6744(18) 0.341(2) 0.3408(11) 0.031(6) Uiso 1 1 d H3 H 1.1791(17) 0.626(2) 0.3159(11) 0.026(5) Uiso 1 1 d H2 H 0.9770(17) 0.326(2) 0.2332(10) 0.026(5) Uiso 1 1 d H21 H 1.0039(18) 0.293(2) 0.3505(11) 0.031(6) Uiso 1 1 d H10 H 0.9586(19) 0.597(2) 0.4050(11) 0.037(6) Uiso 1 1 d H20 H 0.9875(18) 0.186(2) 0.4507(11) 0.034(6) Uiso 1 1 d H2A H 1.3679(19) 0.621(2) 0.2945(12) 0.039(6) Uiso 1 1 d H13 H 0.586(2) 0.656(3) 0.4328(14) 0.057(8) Uiso 1 1 d H14 H 0.6489(18) 0.629(2) 0.3289(11) 0.031(6) Uiso 1 1 d H11 H 0.890(2) 0.622(3) 0.5104(14) 0.051(7) Uiso 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 0.0222(2) 0.0314(3) 0.0427(3) 0.0073(2) 0.0042(2) 0.00054(18) S3 0.0414(3) 0.0437(3) 0.0283(3) 0.0112(2) 0.0003(2) -0.0140(2) S2 0.1304(7) 0.0316(3) 0.0485(4) 0.0061(3) 0.0551(4) 0.0184(4) F2 0.0216(6) 0.0579(9) 0.0684(9) 0.0071(7) 0.0077(6) 0.0011(6) F1 0.0308(6) 0.0333(7) 0.0625(8) -0.0013(6) 0.0066(6) 0.0072(5) F5 0.0304(6) 0.0613(9) 0.0435(7) 0.0188(6) 0.0130(5) 0.0038(6) F4 0.0318(6) 0.0574(8) 0.0471(8) 0.0119(6) -0.0072(6) 0.0013(6) F13 0.0412(7) 0.0465(7) 0.0445(7) 0.0168(6) 0.0017(6) -0.0176(6) F11 0.0834(12) 0.1291(17) 0.0408(8) 0.0378(10) -0.0269(8) -0.0678(12) F12 0.0639(9) 0.0818(11) 0.0364(8) 0.0291(7) -0.0013(7) -0.0243(8) F3 0.0324(6) 0.0338(7) 0.0785(10) 0.0014(7) 0.0099(6) -0.0096(5) F9 0.1418(18) 0.0630(11) 0.0755(12) 0.0103(9) 0.0708(12) 0.0474(12) F15 0.0575(9) 0.0619(10) 0.0680(10) 0.0415(8) 0.0175(7) 0.0205(7) F10 0.204(2) 0.0611(11) 0.0430(9) 0.0199(8) 0.0537(12) 0.0570(14) F14 0.1218(15) 0.0496(9) 0.0400(8) -0.0019(7) 0.0362(9) -0.0044(9) N2 0.0246(7) 0.0172(7) 0.0251(8) -0.0013(6) 0.0057(6) 0.0002(6) F8 0.151(2) 0.0744(13) 0.1052(16) -0.0013(12) 0.0970(16) -0.0299(13) F6 0.169(2) 0.0622(11) 0.0422(9) -0.0197(8) 0.0278(11) 0.0001(12) F7 0.225(3) 0.0635(12) 0.0630(12) 0.0139(9) 0.0949(15) 0.0426(15) N1 0.0269(7) 0.0173(7) 0.0278(8) 0.0014(6) 0.0085(6) -0.0018(6) C1 0.0210(8) 0.0214(9) 0.0314(10) 0.0075(7) 0.0035(7) 0.0001(7) C7 0.0260(9) 0.0189(8) 0.0185(8) 0.0030(6) 0.0025(7) -0.0006(7) C19 0.0324(9) 0.0220(9) 0.0235(9) 0.0030(7) 0.0016(7) -0.0060(7) C16 0.0238(8) 0.0141(7) 0.0228(8) -0.0021(6) 0.0017(7) -0.0015(6) C15 0.0217(8) 0.0187(8) 0.0234(9) -0.0009(7) 0.0015(7) 0.0004(6) C9 0.0267(9) 0.0133(8) 0.0294(9) 0.0001(7) 0.0063(7) -0.0005(6) C3 0.0308(9) 0.0247(9) 0.0237(9) 0.0001(7) 0.0036(7) -0.0013(7) C17 0.0221(8) 0.0175(8) 0.0298(9) -0.0008(7) 0.0009(7) -0.0006(7) C14 0.0289(10) 0.0211(9) 0.0399(11) 0.0003(8) 0.0074(8) 0.0013(7) C8 0.0245(8) 0.0170(8) 0.0253(9) 0.0020(7) 0.0026(7) 0.0016(7) C6 0.0284(9) 0.0206(8) 0.0286(10) 0.0013(7) 0.0067(7) 0.0026(7) C18 0.0248(9) 0.0213(9) 0.0307(10) -0.0011(7) 0.0060(7) -0.0041(7) C21 0.0213(8) 0.0212(9) 0.0279(9) 0.0010(7) 0.0028(7) -0.0014(7) C4 0.0252(9) 0.0166(8) 0.0238(9) 0.0043(7) 0.0043(7) 0.0007(6) C20 0.0253(9) 0.0261(9) 0.0307(10) 0.0052(8) -0.0029(8) -0.0013(7) C2 0.0289(9) 0.0277(9) 0.0292(10) 0.0021(8) -0.0009(8) -0.0030(8) C12 0.0655(15) 0.0187(9) 0.0348(11) -0.0001(8) 0.0267(11) 0.0029(9) C5 0.0247(9) 0.0203(8) 0.0269(9) -0.0008(7) 0.0033(7) -0.0014(7) C10 0.0325(10) 0.0242(9) 0.0315(10) -0.0035(8) 0.0037(8) -0.0024(8) C13 0.0397(12) 0.0239(10) 0.0554(14) 0.0028(9) 0.0258(11) 0.0050(9) C11 0.0572(14) 0.0285(10) 0.0276(10) -0.0049(8) 0.0040(10) -0.0015(9) 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' F F 0.0171 0.0103 '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' S S 0.1246 0.1234 '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 16 6 -1 0.1046 -16 -6 1 0.1046 -8 12 1 0.1873 8 -12 -1 0.1873 0 1 -29 0.1913 0 -1 29 0.1913 4 14 -1 0.1070 17 0 0 0.0692 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle F2 S1 F1 87.60(7) F2 S1 F4 87.29(8) F2 S1 C1 179.40(9) F1 S1 F4 89.29(8) F1 S1 C1 92.58(8) F5 S1 F2 87.86(7) F5 S1 F1 89.89(8) F5 S1 F4 175.11(7) F5 S1 F3 90.64(8) F5 S1 C1 92.71(8) F4 S1 C1 92.14(8) F3 S1 F2 87.43(7) F3 S1 F1 174.97(7) F3 S1 F4 89.77(8) F3 S1 C1 92.39(8) F13 S3 F11 174.80(8) F13 S3 F12 87.64(7) F13 S3 F15 89.28(9) F13 S3 F14 89.70(10) F13 S3 C19 92.95(8) F11 S3 F12 87.21(8) F11 S3 F15 89.80(12) F11 S3 C19 92.19(8) F12 S3 F15 87.73(9) F12 S3 C19 179.23(9) F15 S3 C19 91.78(8) F14 S3 F11 90.84(12) F14 S3 F12 88.04(9) F14 S3 F15 175.69(8) F14 S3 C19 92.46(9) F9 S2 F10 175.22(10) F9 S2 F8 90.91(14) F9 S2 F6 89.29(13) F9 S2 F7 87.80(11) F9 S2 C12 92.75(10) F10 S2 F8 89.72(15) F10 S2 F6 89.72(14) F10 S2 F7 87.49(11) F10 S2 C12 91.96(10) F8 S2 F6 175.57(10) F8 S2 F7 87.82(13) F8 S2 C12 92.04(11) F6 S2 C12 92.38(10) F7 S2 F6 87.76(13) F7 S2 C12 179.43(11) C7 N2 C15 108.14(14) C7 N1 C8 106.27(14) C6 C1 S1 119.30(15) C6 C1 C2 121.61(17) C2 C1 S1 119.09(14) N2 C7 C4 120.10(15) N1 C7 N2 117.29(16) N1 C7 C4 122.61(16) C18 C19 S3 119.29(14) C20 C19 S3 119.60(14) C20 C19 C18 121.10(17) C17 C16 C15 118.67(15) C21 C16 C15 122.78(15) C21 C16 C17 118.39(16) N2 C15 C16 114.03(14) N2 C15 C8 99.84(13) C16 C15 C8 113.11(14) C14 C9 C8 120.24(17) C14 C9 C10 118.97(18) C10 C9 C8 120.51(16) C2 C3 C4 120.45(18) C18 C17 C16 121.45(17) C9 C14 C13 120.9(2) N1 C8 C15 104.94(13) N1 C8 C9 112.92(15) C9 C8 C15 112.73(14) C1 C6 C5 119.19(17) C17 C18 C19 118.75(17) C16 C21 C20 120.90(17) C3 C4 C7 119.02(16) C5 C4 C7 121.01(16) C5 C4 C3 119.97(17) C19 C20 C21 119.33(17) C3 C2 C1 118.64(18) C13 C12 S2 119.97(18) C11 C12 S2 119.07(19) C11 C12 C13 120.95(19) C6 C5 C4 120.08(17) C11 C10 C9 120.4(2) C12 C13 C14 119.1(2) C12 C11 C10 119.6(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 F2 1.5832(12) S1 F1 1.5876(13) S1 F5 1.5742(14) S1 F4 1.5904(14) S1 F3 1.5830(14) S1 C1 1.8015(18) S3 F13 1.5682(13) S3 F11 1.5761(15) S3 F12 1.5799(13) S3 F15 1.5857(17) S3 F14 1.5749(17) S3 C19 1.8055(19) S2 F9 1.5583(19) S2 F10 1.570(2) S2 F8 1.576(3) S2 F6 1.590(2) S2 F7 1.5799(16) S2 C12 1.800(2) N2 C7 1.364(2) N2 C15 1.459(2) N1 C7 1.290(2) N1 C8 1.476(2) C1 C6 1.384(3) C1 C2 1.391(3) C7 C4 1.479(2) C19 C18 1.386(3) C19 C20 1.384(3) C16 C15 1.514(2) C16 C17 1.398(2) C16 C21 1.389(2) C15 C8 1.595(2) C9 C14 1.386(3) C9 C8 1.506(2) C9 C10 1.391(3) C3 C4 1.393(3) C3 C2 1.384(3) C17 C18 1.384(3) C14 C13 1.387(3) C6 C5 1.386(3) C21 C20 1.389(3) C4 C5 1.390(3) C12 C13 1.383(4) C12 C11 1.377(3) C10 C11 1.387(3) 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 16.0000 5.9999 -0.9997 -0.1483 -1.0086 0.0722 -16.0000 -5.9999 0.9997 0.1483 1.0086 -0.0722 -8.0001 12.0000 1.0003 0.0481 -0.0075 -0.9687 8.0001 -12.0000 -1.0003 -0.0481 0.0075 0.9687 0.0001 0.9999 -28.9999 -1.0041 0.0997 -0.0889 -0.0001 -0.9999 28.9999 1.0041 -0.0997 0.0889 3.9999 14.0000 -0.9996 -0.0991 -0.6733 -0.7602 17.0000 -0.0000 0.0001 -0.1025 -0.8600 0.4743