#------------------------------------------------------------------------------ #$Date: 2019-11-17 09:21:32 +0200 (Sun, 17 Nov 2019) $ #$Revision: 229073 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229952.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_7229952 loop_ _publ_author_name 'Chen, Xin' 'Li, Duanxiu' 'Luo, Chun' 'Wang, Jinqiu' 'Deng, Zongwu' 'Zhang, Hailu' _publ_section_title ; Cocrystals of zileuton with enhanced physical stability ; _journal_issue 7 _journal_name_full CrystEngComm _journal_page_first 990 _journal_paper_doi 10.1039/C7CE02150J _journal_volume 20 _journal_year 2018 _chemical_formula_moiety 'C11 H12 N2 O2 S, C6 H6 N2 O' _chemical_formula_sum 'C17 H18 N4 O3 S' _chemical_formula_weight 358.41 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _audit_creation_date 2017-05-17 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337) ; _audit_update_record ; 2017-12-05 deposited with the CCDC. 2018-01-11 downloaded from the CCDC. ; _cell_angle_alpha 75.429(15) _cell_angle_beta 74.117(15) _cell_angle_gamma 79.223(16) _cell_formula_units_Z 4 _cell_length_a 10.2301(19) _cell_length_b 10.609(2) _cell_length_c 17.283(3) _cell_measurement_reflns_used 1028 _cell_measurement_temperature 213.50(10) _cell_measurement_theta_max 73.7090 _cell_measurement_theta_min 4.3130 _cell_volume 1732.0(6) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'XS (Sheldrick, 2008)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 213.50(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.4471 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -49.00 33.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -41.0093 37.0000 -180.0000 82 #__ type_ start__ end____ width___ exp.time_ 2 omega -96.00 3.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -41.0093 125.0000 60.0000 99 #__ type_ start__ end____ width___ exp.time_ 3 omega -69.00 32.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -41.0093 57.0000 0.0000 101 #__ type_ start__ end____ width___ exp.time_ 4 omega -111.00 -20.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -41.0093 -57.0000 -150.0000 91 #__ type_ start__ end____ width___ exp.time_ 5 omega -43.00 15.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -41.0093 37.0000 120.0000 58 #__ type_ start__ end____ width___ exp.time_ 6 omega 42.00 97.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 106.1771 -45.0000 -150.0000 55 #__ type_ start__ end____ width___ exp.time_ 7 omega 24.00 98.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 106.1771 -94.0000 -30.0000 74 #__ type_ start__ end____ width___ exp.time_ 8 omega 35.00 92.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 106.1771 -45.0000 120.0000 57 #__ type_ start__ end____ width___ exp.time_ 9 omega 54.00 99.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 106.1771 -45.0000 0.0000 45 #__ type_ start__ end____ width___ exp.time_ 10 omega 105.00 176.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 106.1771 125.0000 0.0000 71 #__ type_ start__ end____ width___ exp.time_ 11 omega 38.00 109.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 106.1771 -94.0000 120.0000 71 #__ type_ start__ end____ width___ exp.time_ 12 omega 30.00 63.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 106.1771 -30.0000 150.0000 33 #__ type_ start__ end____ width___ exp.time_ 13 omega 38.00 103.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 106.1771 -94.0000 30.0000 65 #__ type_ start__ end____ width___ exp.time_ 14 omega 29.00 149.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 106.1771 -15.0000 -30.0000 120 #__ type_ start__ end____ width___ exp.time_ 15 omega 87.00 120.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 106.1771 -125.0000 -60.0000 33 #__ type_ start__ end____ width___ exp.time_ 16 omega 81.00 176.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 106.1771 45.0000 150.0000 95 #__ type_ start__ end____ width___ exp.time_ 17 omega 39.00 65.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 106.1771 -125.0000 30.0000 26 #__ type_ start__ end____ width___ exp.time_ 18 omega 118.00 152.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 106.1771 30.0000 -90.0000 34 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0525039000 _diffrn_orient_matrix_UB_12 -0.1338924000 _diffrn_orient_matrix_UB_13 -0.0242645000 _diffrn_orient_matrix_UB_21 0.1409900000 _diffrn_orient_matrix_UB_22 0.0045906000 _diffrn_orient_matrix_UB_23 0.0143937000 _diffrn_orient_matrix_UB_31 -0.0477512000 _diffrn_orient_matrix_UB_32 -0.0702164000 _diffrn_orient_matrix_UB_33 0.0905422000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.1218 _diffrn_reflns_av_unetI/netI 0.1784 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 12307 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 67.074 _diffrn_reflns_theta_max 67.074 _diffrn_reflns_theta_min 4.341 _diffrn_source 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.874 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.79490 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_density_diffrn 1.375 _exptl_crystal_description block _exptl_crystal_F_000 752 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.550 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.078 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 459 _refine_ls_number_reflns 6186 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.053 _refine_ls_R_factor_all 0.1749 _refine_ls_R_factor_gt 0.0802 _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^)] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1333 _refine_ls_wR_factor_ref 0.1934 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2579 _reflns_number_total 6186 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; 20170516nami2.res created by SHELXL-2014/7 TITL 20170516nami2 in P-1 #2 CELL 1.54184 10.230056 10.609344 17.282521 75.4286 74.1174 79.2234 ZERR 4 0.001866 0.002143 0.002719 0.0154 0.0149 0.0162 LATT 1 SFAC C H N O S UNIT 68 72 16 12 4 EQIV $1 +X,1+Y,+Z EQIV $2 -1+X,1+Y,+Z L.S. 40 PLAN 20 TEMP -59.65(10) HTAB O1 N7_$1 HTAB O3 N5_$2 HTAB N8 O5 BOND htab fmap 2 acta SHEL 999 0.837 REM REM REM WGHT 0.000000 FVAR 2.24689 S1 5 0.640235 0.538820 0.225558 11.00000 0.04201 0.03107 = 0.05507 -0.01444 -0.01610 0.00218 S2 5 0.060145 0.483967 0.266894 11.00000 0.07448 0.04647 = 0.05601 -0.00848 -0.02153 0.00851 O1 4 0.570544 0.819532 0.235232 11.00000 0.04020 0.03856 = 0.03757 -0.01207 -0.01104 0.00245 H1 2 0.534873 0.875691 0.255833 11.00000 -1.50000 O2 4 0.383816 0.901677 0.083838 11.00000 0.03382 0.04349 = 0.04005 0.00240 -0.01239 -0.00818 O3 4 0.082064 0.828348 0.232595 11.00000 0.04006 0.03594 = 0.03890 -0.01041 -0.01789 0.00189 H3A 2 0.083441 0.915874 0.249880 11.00000 -1.50000 O4 4 -0.120806 0.916317 0.088918 11.00000 0.03367 0.04484 = 0.04084 0.00550 -0.01378 -0.00530 O5 4 0.698160 0.372549 0.462289 11.00000 0.03318 0.05534 = 0.06288 -0.03018 -0.01205 0.00220 O6 4 0.199828 0.360939 0.466559 11.00000 0.03657 0.05060 = 0.05955 -0.03000 -0.01014 -0.00131 C1 1 0.676092 0.423301 0.164264 11.00000 0.04751 0.02523 = 0.04442 -0.00985 0.00375 -0.00579 C2 1 0.795146 0.332590 0.153507 11.00000 0.04284 0.03537 = 0.06213 -0.01004 0.00043 -0.00591 AFIX 43 H2 2 0.863657 0.326678 0.181522 11.00000 -1.20000 AFIX 0 C3 1 0.806113 0.253438 0.100200 11.00000 0.07004 0.02991 = 0.07993 -0.01299 0.01908 -0.00358 AFIX 43 H3 2 0.884669 0.191808 0.091256 11.00000 -1.20000 AFIX 0 C4 1 0.704525 0.260763 0.058358 11.00000 0.07132 0.05652 = 0.05972 -0.03488 0.00951 -0.01535 AFIX 43 H4 2 0.716749 0.204952 0.021767 11.00000 -1.20000 AFIX 0 C5 1 0.588857 0.347143 0.069858 11.00000 0.06438 0.04457 = 0.05067 -0.01714 -0.00025 -0.01866 AFIX 43 H5 2 0.520111 0.350374 0.042525 11.00000 -1.20000 AFIX 0 C6 1 0.573543 0.432421 0.123825 11.00000 0.04920 0.03562 = 0.03619 -0.01279 -0.00671 -0.00410 C7 1 0.465322 0.532274 0.144843 11.00000 0.04022 0.04420 = 0.03702 -0.00496 -0.01121 -0.00826 AFIX 43 H7 2 0.386523 0.551005 0.123917 11.00000 -1.20000 AFIX 0 C8 1 0.484736 0.597673 0.196992 11.00000 0.02889 0.02922 = 0.04501 -0.00325 -0.00988 -0.00246 C9 1 0.390126 0.711303 0.228959 11.00000 0.03073 0.03237 = 0.03394 0.00135 -0.00597 -0.00366 AFIX 13 H9 2 0.309496 0.727838 0.204942 11.00000 -1.20000 AFIX 0 C10 1 0.336994 0.681215 0.323207 11.00000 0.03928 0.05706 = 0.03638 -0.00759 -0.00207 -0.00363 AFIX 137 H10A 2 0.288394 0.604848 0.340173 11.00000 -1.50000 H10B 2 0.275368 0.756039 0.340038 11.00000 -1.50000 H10C 2 0.413735 0.663796 0.348805 11.00000 -1.50000 AFIX 0 C11 1 0.471978 0.897306 0.119275 11.00000 0.03125 0.02332 = 0.03450 -0.00805 -0.00495 0.00437 C12 1 0.137702 0.399760 0.187746 11.00000 0.05455 0.04747 = 0.05790 -0.02440 -0.01663 0.00237 C13 1 0.214527 0.276798 0.194652 11.00000 0.07762 0.04172 = 0.10758 -0.01700 -0.03471 0.00578 AFIX 43 H13 2 0.233819 0.230678 0.245160 11.00000 -1.20000 AFIX 0 C14 1 0.261434 0.224550 0.125829 11.00000 0.06411 0.04387 = 0.14650 -0.04647 -0.01989 0.01884 AFIX 43 H14 2 0.311457 0.140283 0.129162 11.00000 -1.20000 AFIX 0 C15 1 0.235302 0.295969 0.050463 11.00000 0.06922 0.06643 = 0.09967 -0.04846 0.00306 -0.00281 AFIX 43 H15 2 0.270467 0.259542 0.003498 11.00000 -1.20000 AFIX 0 C16 1 0.160201 0.416906 0.043492 11.00000 0.07400 0.06027 = 0.05858 -0.03536 -0.00107 -0.00780 AFIX 43 H16 2 0.143612 0.462921 -0.007695 11.00000 -1.20000 AFIX 0 C17 1 0.107252 0.472934 0.113784 11.00000 0.04893 0.04056 = 0.04259 -0.01159 -0.00503 -0.00620 C18 1 0.019635 0.595335 0.119497 11.00000 0.04466 0.03475 = 0.03325 -0.01010 -0.00532 -0.00442 AFIX 43 H18 2 -0.010144 0.654578 0.075380 11.00000 -1.20000 AFIX 0 C19 1 -0.014824 0.612850 0.201707 11.00000 0.03549 0.02764 = 0.03880 -0.00518 -0.01138 -0.00374 C20 1 -0.109790 0.728230 0.232898 11.00000 0.03565 0.03328 = 0.03166 -0.00562 -0.00609 -0.00463 AFIX 13 H20 2 -0.189534 0.745891 0.208003 11.00000 -1.20000 AFIX 0 C21 1 -0.164967 0.703854 0.326973 11.00000 0.05373 0.04663 = 0.03232 -0.00591 -0.00322 -0.00697 AFIX 137 H21A 2 -0.214115 0.627748 0.345469 11.00000 -1.50000 H21B 2 -0.226488 0.780164 0.341609 11.00000 -1.50000 H21C 2 -0.089067 0.688289 0.353119 11.00000 -1.50000 AFIX 0 C22 1 -0.025404 0.909244 0.120648 11.00000 0.04169 0.01957 = 0.03494 -0.00458 -0.00740 0.00209 C23 1 0.819965 0.332413 0.453711 11.00000 0.04160 0.03536 = 0.03309 -0.00696 -0.00465 -0.00903 C24 1 0.885069 0.218447 0.411775 11.00000 0.04027 0.03393 = 0.04442 -0.01222 -0.01092 0.00021 C25 1 1.008974 0.145242 0.420880 11.00000 0.08077 0.06509 = 0.10271 -0.05080 -0.05233 0.01002 AFIX 43 H25 2 1.057352 0.163426 0.455039 11.00000 -1.20000 AFIX 0 C26 1 1.060084 0.045228 0.378947 11.00000 0.07052 0.08247 = 0.13253 -0.06990 -0.05527 0.02225 AFIX 43 H26 2 1.147349 0.000082 0.382205 11.00000 -1.20000 AFIX 0 C27 1 0.874056 0.080057 0.327213 11.00000 0.06982 0.06286 = 0.06599 -0.03042 -0.02822 0.00278 AFIX 43 H27 2 0.827219 0.058236 0.293545 11.00000 -1.20000 AFIX 0 C28 1 0.812004 0.184252 0.365183 11.00000 0.06403 0.04981 = 0.07490 -0.02971 -0.02448 0.00412 AFIX 43 H28 2 0.725522 0.228892 0.359569 11.00000 -1.20000 AFIX 0 C29 1 0.325900 0.326664 0.451906 11.00000 0.03784 0.03491 = 0.03584 -0.00980 -0.00915 -0.00224 C30 1 0.385829 0.214451 0.409760 11.00000 0.02953 0.03338 = 0.03422 -0.01528 -0.00672 0.00295 C31 1 0.363741 0.086299 0.451053 11.00000 0.06330 0.04150 = 0.04265 -0.01444 -0.00423 -0.00517 AFIX 43 H31 2 0.312743 0.068888 0.505959 11.00000 -1.20000 AFIX 0 C32 1 0.417739 -0.013550 0.410094 11.00000 0.07689 0.03694 = 0.07100 -0.01439 -0.02509 0.00362 AFIX 43 H32 2 0.403428 -0.099634 0.438758 11.00000 -1.20000 AFIX 0 C33 1 0.507054 0.127935 0.293318 11.00000 0.06975 0.05316 = 0.05028 -0.02687 0.00484 -0.00676 AFIX 43 H33 2 0.555228 0.142900 0.237759 11.00000 -1.20000 AFIX 0 C34 1 0.459803 0.234606 0.329053 11.00000 0.05777 0.03878 = 0.05368 -0.01013 -0.00267 -0.01697 AFIX 43 H34 2 0.477453 0.319368 0.299218 11.00000 -1.20000 AFIX 0 N1 3 0.452878 0.834112 0.204157 11.00000 0.03407 0.03550 = 0.03229 -0.00862 -0.01030 0.00195 N2 3 0.586322 0.953117 0.085887 11.00000 0.03877 0.04894 = 0.03457 0.00428 -0.01003 -0.01381 AFIX 93 H2A 2 0.601743 0.996549 0.035044 11.00000 -1.20000 H2B 2 0.645685 0.946187 0.114894 11.00000 -1.20000 AFIX 0 N3 3 -0.040848 0.847424 0.205550 11.00000 0.02678 0.03415 = 0.03321 -0.00786 -0.00658 0.00090 N4 3 0.090236 0.962361 0.085265 11.00000 0.03677 0.04023 = 0.04010 -0.00003 -0.01640 -0.00200 AFIX 93 H4A 2 0.103419 1.007229 0.034771 11.00000 -1.20000 H4B 2 0.152654 0.952217 0.112628 11.00000 -1.20000 AFIX 0 N5 3 0.992048 0.009001 0.333845 11.00000 0.05740 0.04404 = 0.06247 -0.02702 -0.01957 0.00606 N6 3 0.904067 0.383872 0.481018 11.00000 0.02761 0.05030 = 0.04642 -0.02787 -0.00072 -0.00360 AFIX 93 H6A 2 0.872459 0.448769 0.506111 11.00000 -1.20000 H6B 2 0.990387 0.352451 0.473690 11.00000 -1.20000 AFIX 0 N7 3 0.489302 0.003890 0.332114 11.00000 0.05378 0.05387 = 0.05613 -0.03218 -0.01634 0.00731 N8 3 0.410331 0.388697 0.468663 11.00000 0.03335 0.04289 = 0.05407 -0.02365 -0.00607 0.00175 AFIX 93 H8A 2 0.379031 0.456717 0.490907 11.00000 -1.20000 H8B 2 0.497829 0.361966 0.457574 11.00000 -1.20000 AFIX 0 HKLF 4 REM 20170516nami2 in P-1 #2 REM R1 = 0.0802 for 2579 Fo > 4sig(Fo) and 0.1749 for all 6186 data REM 459 parameters refined using 0 restraints END WGHT 0.0507 0.0470 REM Instructions for potential hydrogen bonds HTAB O1 N7_$1 HTAB O3 N5_$2 HTAB C9 O3 EQIV $3 x-1, y, z HTAB C20 S1_$3 HTAB C20 O1_$3 HTAB C34 S1 EQIV $4 -x+1, -y+2, -z HTAB N2 O2_$4 EQIV $5 x+1, y, z HTAB N2 O4_$5 EQIV $6 -x, -y+2, -z HTAB N4 O4_$6 HTAB N4 O2 EQIV $7 -x+1, -y+1, -z+1 HTAB N6 O6_$7 HTAB N6 O6_$5 HTAB N8 O5_$7 HTAB N8 O5 REM Highest difference peak 0.550, deepest hole -0.433, 1-sigma level 0.078 Q1 1 0.1472 0.5411 0.2258 11.00000 0.05 0.55 Q2 1 0.5577 0.4894 0.2673 11.00000 0.05 0.50 Q3 1 0.7709 0.4249 0.1927 11.00000 0.05 0.33 Q4 1 0.1029 0.4035 0.2061 11.00000 0.05 0.32 Q5 1 0.7287 0.3791 0.4471 11.00000 0.05 0.31 Q6 1 0.2536 0.6834 0.3313 11.00000 0.05 0.30 Q7 1 -0.1446 0.6989 0.3048 11.00000 0.05 0.30 Q8 1 -0.0360 0.5797 0.1563 11.00000 0.05 0.30 Q9 1 0.9900 0.4004 0.4545 11.00000 0.05 0.27 Q10 1 0.8800 0.3110 0.3134 11.00000 0.05 0.27 Q11 1 0.6019 0.3965 0.2760 11.00000 0.05 0.26 Q12 1 -0.0831 0.9374 0.2138 11.00000 0.05 0.26 Q13 1 0.3181 0.8809 0.1170 11.00000 0.05 0.26 Q14 1 -0.1611 0.7773 0.3484 11.00000 0.05 0.26 Q15 1 0.2489 0.4873 0.2527 11.00000 0.05 0.25 Q16 1 0.2722 0.1310 0.1344 11.00000 0.05 0.25 Q17 1 -0.0930 0.8147 0.2255 11.00000 0.05 0.25 Q18 1 0.6986 0.1406 0.2201 11.00000 0.05 0.25 Q19 1 0.6912 0.2605 0.4907 11.00000 0.05 0.25 Q20 1 0.3436 0.2933 -0.0692 11.00000 0.05 0.25 REM The information below was added by Olex2. REM REM R1 = 0.0802 for 2579 Fo > 4sig(Fo) and 0.1749 for all 13058 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.55, deepest hole -0.43 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.1749 REM R1_gt = 0.0802 REM wR_ref = 0.1934 REM GOOF = 1.053 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 13058 REM Reflections_gt = 2579 REM Parameters = n/a REM Hole = -0.43 REM Peak = 0.55 REM Flack = n/a ; _cod_data_source_file c7ce02150j2.cif _cod_data_source_block 20170516nami2 _cod_depositor_comments 'Adding full bibliography for 7229950--7229953.cif.' _cod_database_code 7229952 _shelx_shelxl_version_number 2014/7 _chemical_oxdiff_usercomment CHNOS _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 N(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Ternary CH refined with riding coordinates: C9(H9), C20(H20) 2.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18), C25(H25), C26(H26), C27(H27), C28(H28), C31(H31), C32(H32), C33(H33), C34(H34) 2.c X=CH2 refined with riding coordinates: N2(H2A,H2B), N4(H4A,H4B), N6(H6A,H6B), N8(H8A,H8B) 2.d Idealised Me refined as rotating group: C10(H10A,H10B,H10C), C21(H21A,H21B,H21C) ; _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 S1 S 0.64024(18) 0.53882(16) 0.22556(11) 0.0417(4) Uani 1 1 d . S2 S 0.0601(2) 0.4840(2) 0.26689(13) 0.0604(6) Uani 1 1 d . O1 O 0.5705(5) 0.8195(5) 0.2352(3) 0.0387(11) Uani 1 1 d . H1 H 0.535(8) 0.876(8) 0.256(5) 0.058 Uiso 1 1 d R O2 O 0.3838(4) 0.9017(4) 0.0838(3) 0.0400(11) Uani 1 1 d . O3 O 0.0821(5) 0.8283(4) 0.2326(3) 0.0370(10) Uani 1 1 d . H3A H 0.083(7) 0.916(7) 0.250(4) 0.056 Uiso 1 1 d R O4 O -0.1208(4) 0.9163(4) 0.0889(3) 0.0415(11) Uani 1 1 d . O5 O 0.6982(5) 0.3725(5) 0.4623(3) 0.0481(12) Uani 1 1 d . O6 O 0.1998(5) 0.3609(5) 0.4666(3) 0.0463(12) Uani 1 1 d . C1 C 0.6761(7) 0.4233(6) 0.1643(4) 0.0414(16) Uani 1 1 d . C2 C 0.7951(7) 0.3326(7) 0.1535(4) 0.0493(18) Uani 1 1 d . H2 H 0.8637 0.3267 0.1815 0.059 Uiso 1 1 calc R C3 C 0.8061(9) 0.2534(7) 0.1002(5) 0.068(3) Uani 1 1 d . H3 H 0.8847 0.1918 0.0913 0.081 Uiso 1 1 calc R C4 C 0.7045(9) 0.2608(8) 0.0584(5) 0.062(2) Uani 1 1 d . H4 H 0.7167 0.2050 0.0218 0.075 Uiso 1 1 calc R C5 C 0.5889(8) 0.3471(7) 0.0699(4) 0.053(2) Uani 1 1 d . H5 H 0.5201 0.3504 0.0425 0.064 Uiso 1 1 calc R C6 C 0.5735(7) 0.4324(7) 0.1238(4) 0.0403(16) Uani 1 1 d . C7 C 0.4653(7) 0.5323(7) 0.1448(4) 0.0404(16) Uani 1 1 d . H7 H 0.3865 0.5510 0.1239 0.048 Uiso 1 1 calc R C8 C 0.4847(6) 0.5977(6) 0.1970(4) 0.0352(14) Uani 1 1 d . C9 C 0.3901(6) 0.7113(6) 0.2290(4) 0.0343(14) Uani 1 1 d . H9 H 0.3095 0.7278 0.2049 0.041 Uiso 1 1 calc R C10 C 0.3370(7) 0.6812(7) 0.3232(4) 0.0464(18) Uani 1 1 d . H10A H 0.2884 0.6048 0.3402 0.070 Uiso 1 1 calc GR H10B H 0.2754 0.7560 0.3400 0.070 Uiso 1 1 calc GR H10C H 0.4137 0.6638 0.3488 0.070 Uiso 1 1 calc GR C11 C 0.4720(6) 0.8973(6) 0.1193(4) 0.0310(13) Uani 1 1 d . C12 C 0.1377(8) 0.3998(8) 0.1877(5) 0.0514(19) Uani 1 1 d . C13 C 0.2145(9) 0.2768(8) 0.1947(6) 0.075(3) Uani 1 1 d . H13 H 0.2338 0.2307 0.2452 0.090 Uiso 1 1 calc R C14 C 0.2614(9) 0.2246(9) 0.1258(7) 0.084(3) Uani 1 1 d . H14 H 0.3115 0.1403 0.1292 0.101 Uiso 1 1 calc R C15 C 0.2353(9) 0.2960(10) 0.0505(6) 0.078(3) Uani 1 1 d . H15 H 0.2705 0.2595 0.0035 0.094 Uiso 1 1 calc R C16 C 0.1602(9) 0.4169(8) 0.0435(5) 0.063(2) Uani 1 1 d . H16 H 0.1436 0.4629 -0.0077 0.076 Uiso 1 1 calc R C17 C 0.1073(8) 0.4729(7) 0.1138(4) 0.0446(17) Uani 1 1 d . C18 C 0.0196(7) 0.5953(6) 0.1195(4) 0.0379(15) Uani 1 1 d . H18 H -0.0101 0.6546 0.0754 0.045 Uiso 1 1 calc R C19 C -0.0148(6) 0.6128(6) 0.2017(4) 0.0338(14) Uani 1 1 d . C20 C -0.1098(7) 0.7282(6) 0.2329(4) 0.0341(14) Uani 1 1 d . H20 H -0.1895 0.7459 0.2080 0.041 Uiso 1 1 calc R C21 C -0.1650(7) 0.7039(7) 0.3270(4) 0.0460(18) Uani 1 1 d . H21A H -0.2141 0.6277 0.3455 0.069 Uiso 1 1 calc GR H21B H -0.2265 0.7802 0.3416 0.069 Uiso 1 1 calc GR H21C H -0.0891 0.6883 0.3531 0.069 Uiso 1 1 calc GR C22 C -0.0254(7) 0.9092(6) 0.1206(4) 0.0335(14) Uani 1 1 d . C23 C 0.8200(7) 0.3324(6) 0.4537(4) 0.0370(15) Uani 1 1 d . C24 C 0.8851(7) 0.2184(7) 0.4118(4) 0.0393(15) Uani 1 1 d . C25 C 1.0090(9) 0.1452(9) 0.4209(6) 0.073(3) Uani 1 1 d . H25 H 1.0574 0.1634 0.4550 0.088 Uiso 1 1 calc R C26 C 1.0601(10) 0.0452(10) 0.3789(6) 0.084(3) Uani 1 1 d . H26 H 1.1473 0.0001 0.3822 0.101 Uiso 1 1 calc R C27 C 0.8741(9) 0.0801(9) 0.3272(5) 0.062(2) Uani 1 1 d . H27 H 0.8272 0.0582 0.2935 0.075 Uiso 1 1 calc R C28 C 0.8120(9) 0.1843(8) 0.3652(5) 0.060(2) Uani 1 1 d . H28 H 0.7255 0.2289 0.3596 0.072 Uiso 1 1 calc R C29 C 0.3259(7) 0.3267(6) 0.4519(4) 0.0360(15) Uani 1 1 d . C30 C 0.3858(6) 0.2145(6) 0.4098(4) 0.0320(13) Uani 1 1 d . C31 C 0.3637(8) 0.0863(7) 0.4511(4) 0.0500(19) Uani 1 1 d . H31 H 0.3127 0.0689 0.5060 0.060 Uiso 1 1 calc R C32 C 0.4177(9) -0.0136(8) 0.4101(5) 0.061(2) Uani 1 1 d . H32 H 0.4034 -0.0996 0.4388 0.073 Uiso 1 1 calc R C33 C 0.5071(9) 0.1279(8) 0.2933(5) 0.059(2) Uani 1 1 d . H33 H 0.5552 0.1429 0.2378 0.071 Uiso 1 1 calc R C34 C 0.4598(8) 0.2346(7) 0.3291(4) 0.0507(19) Uani 1 1 d . H34 H 0.4775 0.3194 0.2992 0.061 Uiso 1 1 calc R N1 N 0.4529(5) 0.8341(5) 0.2042(3) 0.0341(12) Uani 1 1 d . N2 N 0.5863(5) 0.9531(5) 0.0859(3) 0.0418(14) Uani 1 1 d . H2A H 0.6017 0.9965 0.0350 0.050 Uiso 1 1 calc R H2B H 0.6457 0.9462 0.1149 0.050 Uiso 1 1 calc R N3 N -0.0408(5) 0.8474(5) 0.2056(3) 0.0320(12) Uani 1 1 d . N4 N 0.0902(5) 0.9624(5) 0.0853(3) 0.0395(13) Uani 1 1 d . H4A H 0.1034 1.0072 0.0348 0.047 Uiso 1 1 calc R H4B H 0.1527 0.9522 0.1126 0.047 Uiso 1 1 calc R N5 N 0.9920(7) 0.0090(6) 0.3338(4) 0.0523(16) Uani 1 1 d . N6 N 0.9041(5) 0.3839(6) 0.4810(3) 0.0400(13) Uani 1 1 d . H6A H 0.8725 0.4488 0.5061 0.048 Uiso 1 1 calc R H6B H 0.9904 0.3525 0.4737 0.048 Uiso 1 1 calc R N7 N 0.4893(7) 0.0039(6) 0.3321(4) 0.0520(16) Uani 1 1 d . N8 N 0.4103(6) 0.3887(5) 0.4687(3) 0.0427(14) Uani 1 1 d . H8A H 0.3790 0.4567 0.4909 0.051 Uiso 1 1 calc R H8B H 0.4978 0.3620 0.4576 0.051 Uiso 1 1 calc R 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 0.0420(9) 0.0311(9) 0.0551(10) -0.0144(7) -0.0161(8) 0.0022(7) S2 0.0745(15) 0.0465(11) 0.0560(12) -0.0085(9) -0.0215(11) 0.0085(10) O1 0.040(3) 0.039(3) 0.038(3) -0.012(2) -0.011(2) 0.002(2) O2 0.034(3) 0.043(3) 0.040(2) 0.002(2) -0.012(2) -0.008(2) O3 0.040(3) 0.036(3) 0.039(2) -0.010(2) -0.018(2) 0.002(2) O4 0.034(3) 0.045(3) 0.041(3) 0.005(2) -0.014(2) -0.005(2) O5 0.033(3) 0.055(3) 0.063(3) -0.030(3) -0.012(2) 0.002(2) O6 0.037(3) 0.051(3) 0.060(3) -0.030(2) -0.010(2) -0.001(2) C1 0.048(4) 0.025(3) 0.044(4) -0.010(3) 0.004(3) -0.006(3) C2 0.043(4) 0.035(4) 0.062(5) -0.010(3) 0.000(4) -0.006(3) C3 0.070(6) 0.030(4) 0.080(6) -0.013(4) 0.019(5) -0.004(4) C4 0.071(6) 0.057(5) 0.060(5) -0.035(4) 0.010(4) -0.015(4) C5 0.064(5) 0.045(5) 0.051(4) -0.017(3) 0.000(4) -0.019(4) C6 0.049(4) 0.036(4) 0.036(4) -0.013(3) -0.007(3) -0.004(3) C7 0.040(4) 0.044(4) 0.037(4) -0.005(3) -0.011(3) -0.008(3) C8 0.029(3) 0.029(3) 0.045(4) -0.003(3) -0.010(3) -0.002(3) C9 0.031(3) 0.032(3) 0.034(3) 0.001(3) -0.006(3) -0.004(3) C10 0.039(4) 0.057(5) 0.036(4) -0.008(3) -0.002(3) -0.004(3) C11 0.031(3) 0.023(3) 0.034(3) -0.008(2) -0.005(3) 0.004(3) C12 0.055(5) 0.047(5) 0.058(5) -0.024(4) -0.017(4) 0.002(4) C13 0.078(7) 0.042(5) 0.108(8) -0.017(5) -0.035(6) 0.006(5) C14 0.064(6) 0.044(5) 0.147(10) -0.046(6) -0.020(6) 0.019(5) C15 0.069(6) 0.066(7) 0.100(8) -0.048(6) 0.003(6) -0.003(5) C16 0.074(6) 0.060(6) 0.059(5) -0.035(4) -0.001(4) -0.008(5) C17 0.049(4) 0.041(4) 0.043(4) -0.012(3) -0.005(3) -0.006(3) C18 0.045(4) 0.035(4) 0.033(3) -0.010(3) -0.005(3) -0.004(3) C19 0.035(4) 0.028(3) 0.039(4) -0.005(3) -0.011(3) -0.004(3) C20 0.036(3) 0.033(3) 0.032(3) -0.006(3) -0.006(3) -0.005(3) C21 0.054(5) 0.047(4) 0.032(4) -0.006(3) -0.003(3) -0.007(4) C22 0.042(4) 0.020(3) 0.035(3) -0.005(2) -0.007(3) 0.002(3) C23 0.042(4) 0.035(4) 0.033(3) -0.007(3) -0.005(3) -0.009(3) C24 0.040(4) 0.034(4) 0.044(4) -0.012(3) -0.011(3) 0.000(3) C25 0.081(7) 0.065(6) 0.103(7) -0.051(5) -0.052(6) 0.010(5) C26 0.071(6) 0.082(7) 0.133(9) -0.070(7) -0.055(6) 0.022(5) C27 0.070(6) 0.063(6) 0.066(5) -0.030(4) -0.028(5) 0.003(5) C28 0.064(5) 0.050(5) 0.075(6) -0.030(4) -0.024(5) 0.004(4) C29 0.038(4) 0.035(4) 0.036(3) -0.010(3) -0.009(3) -0.002(3) C30 0.030(3) 0.033(3) 0.034(3) -0.015(3) -0.007(3) 0.003(3) C31 0.063(5) 0.042(4) 0.043(4) -0.014(3) -0.004(4) -0.005(4) C32 0.077(6) 0.037(4) 0.071(6) -0.014(4) -0.025(5) 0.004(4) C33 0.070(6) 0.053(5) 0.050(5) -0.027(4) 0.005(4) -0.007(4) C34 0.058(5) 0.039(4) 0.054(4) -0.010(3) -0.003(4) -0.017(4) N1 0.034(3) 0.035(3) 0.032(3) -0.009(2) -0.010(2) 0.002(2) N2 0.039(3) 0.049(4) 0.035(3) 0.004(3) -0.010(2) -0.014(3) N3 0.027(3) 0.034(3) 0.033(3) -0.008(2) -0.007(2) 0.001(2) N4 0.037(3) 0.040(3) 0.040(3) 0.000(2) -0.016(3) -0.002(3) N5 0.057(4) 0.044(4) 0.062(4) -0.027(3) -0.020(3) 0.006(3) N6 0.028(3) 0.050(4) 0.046(3) -0.028(3) -0.001(2) -0.004(2) N7 0.054(4) 0.054(4) 0.056(4) -0.032(3) -0.016(3) 0.007(3) N8 0.033(3) 0.043(3) 0.054(4) -0.024(3) -0.006(3) 0.002(3) 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 C1 S1 C8 90.4(3) C19 S2 C12 92.5(3) C2 C1 S1 125.5(6) C6 C1 S1 112.1(5) C6 C1 C2 122.4(7) C3 C2 C1 116.5(8) C2 C3 C4 122.4(8) C5 C4 C3 121.0(7) C4 C5 C6 118.7(8) C1 C6 C5 119.0(7) C1 C6 C7 111.2(6) C5 C6 C7 129.8(7) C8 C7 C6 114.5(6) C7 C8 S1 111.9(5) C7 C8 C9 126.9(6) C9 C8 S1 121.2(5) C8 C9 C10 113.0(5) N1 C9 C8 113.3(5) N1 C9 C10 108.4(5) O2 C11 N1 119.5(6) O2 C11 N2 124.7(6) N2 C11 N1 115.7(5) C13 C12 S2 126.9(7) C13 C12 C17 123.2(8) C17 C12 S2 109.9(6) C14 C13 C12 118.1(9) C13 C14 C15 120.3(9) C16 C15 C14 121.7(9) C15 C16 C17 119.6(9) C12 C17 C16 117.1(7) C12 C17 C18 115.3(6) C16 C17 C18 127.6(7) C19 C18 C17 109.8(6) C18 C19 S2 112.5(5) C18 C19 C20 125.4(6) C20 C19 S2 122.1(5) C19 C20 C21 114.5(5) N3 C20 C19 110.7(5) N3 C20 C21 108.7(5) O4 C22 N3 118.4(6) O4 C22 N4 126.3(6) N4 C22 N3 115.1(5) O5 C23 C24 121.4(6) O5 C23 N6 122.8(6) N6 C23 C24 115.8(6) C25 C24 C23 123.4(7) C25 C24 C28 119.3(7) C28 C24 C23 117.2(6) C26 C25 C24 118.7(8) N5 C26 C25 123.4(8) N5 C27 C28 126.3(8) C24 C28 C27 116.0(8) O6 C29 C30 119.6(6) O6 C29 N8 122.5(6) N8 C29 C30 117.8(6) C31 C30 C29 120.3(6) C34 C30 C29 121.4(6) C34 C30 C31 118.2(6) C32 C31 C30 118.7(7) N7 C32 C31 123.9(8) N7 C33 C34 124.5(7) C33 C34 C30 118.3(7) O1 N1 C9 111.4(5) O1 N1 C11 113.9(5) C11 N1 C9 116.0(5) O3 N3 C20 111.9(5) O3 N3 C22 113.4(5) C22 N3 C20 115.6(5) C27 N5 C26 116.0(7) C32 N7 C33 116.2(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C1 1.741(7) S1 C8 1.751(6) S2 C12 1.748(8) S2 C19 1.741(6) O1 N1 1.416(7) O2 C11 1.210(7) O3 N3 1.421(6) O4 C22 1.226(7) O5 C23 1.220(8) O6 C29 1.246(8) C1 C2 1.404(10) C1 C6 1.388(9) C2 C3 1.365(10) C3 C4 1.401(12) C4 C5 1.355(11) C5 C6 1.416(9) C6 C7 1.419(9) C7 C8 1.341(9) C8 C9 1.517(9) C9 C10 1.539(8) C9 N1 1.475(8) C11 N1 1.427(7) C11 N2 1.330(8) C12 C13 1.387(11) C12 C17 1.401(10) C13 C14 1.368(12) C14 C15 1.400(13) C15 C16 1.362(12) C16 C17 1.416(10) C17 C18 1.442(10) C18 C19 1.418(8) C19 C20 1.528(9) C20 C21 1.539(8) C20 N3 1.473(8) C22 N3 1.427(7) C22 N4 1.331(8) C23 C24 1.519(9) C23 N6 1.337(8) C24 C25 1.384(11) C24 C28 1.384(10) C25 C26 1.377(12) C26 N5 1.337(10) C27 C28 1.389(11) C27 N5 1.315(10) C29 C30 1.498(9) C29 N8 1.307(8) C30 C31 1.395(9) C30 C34 1.377(9) C31 C32 1.369(10) C32 N7 1.331(10) C33 C34 1.371(10) C33 N7 1.339(10) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N7 0.75(7) 2.03(7) 2.756(7) 161(8) 1_565 O3 H3A N5 1.05(7) 1.89(7) 2.780(7) 140(6) 1_465 N8 H8B O5 0.87 2.10 2.890(7) 151.1 .