#------------------------------------------------------------------------------ #$Date: 2021-10-12 04:10:32 +0300 (Tue, 12 Oct 2021) $ #$Revision: 269896 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/49/1564903.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_1564903 loop_ _publ_author_name 'Galukhin, Andrey Vladimirovich' 'Nikolaev, Ilya' 'Nosov, Roman V.' 'Islamov, Daut' 'Vyazovkin, Sergey' _publ_section_title ; Solvent-induced changes in reactivity of tricyanate ester undergoing thermal polymerization ; _journal_name_full 'Polymer Chemistry' _journal_paper_doi 10.1039/D1PY01088C _journal_year 2021 _chemical_formula_moiety 'C23 H15 N3 O3' _chemical_formula_sum 'C23 H15 N3 O3' _chemical_formula_weight 381.38 _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 geom _atom_sites_solution_primary dual _audit_creation_date 2020-11-02 _audit_creation_method ; Olex2 1.3-ac4 (compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032) ; _audit_update_record ; 2021-07-26 deposited with the CCDC. 2021-10-11 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 98.2240(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.6119(2) _cell_length_b 13.3664(2) _cell_length_c 8.87420(10) _cell_measurement_reflns_used 7449 _cell_measurement_temperature 99.9(4) _cell_measurement_theta_max 75.9530 _cell_measurement_theta_min 2.8660 _cell_volume 1832.78(4) _computing_cell_refinement 'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)' _computing_data_collection 'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)' _computing_data_reduction 'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)' _computing_molecular_graphics 'Olex2 1.3-ac4 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3-ac4 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2016/6 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 99.9(4) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.960 _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 -27.00 28.00 0.50 0.05 -- -47.45 19.00 -90.00 110 2 \w -25.00 28.00 0.50 0.05 -- -47.45 19.00 -30.00 106 3 \w 57.00 89.00 0.50 0.05 -- 47.45 149.00 -60.00 64 4 \w 76.00 119.00 0.50 0.05 -- 47.45 125.00 -90.00 86 5 \w 93.00 176.00 0.50 0.06 -- 105.86 45.00 -30.00 166 6 \w 58.00 84.00 0.50 0.05 -- 47.45-122.00 56.00 52 7 \w 58.00 104.00 0.50 0.06 -- 105.86 -94.00 90.00 92 8 \w 35.00 93.00 0.50 0.06 -- 105.86 -77.00 60.00 116 9 \w 41.00 67.00 0.50 0.06 -- 105.86 -61.00 -60.00 52 10 \w 40.00 66.00 0.50 0.06 -- 105.86 -61.00-120.00 52 11 \w 40.00 66.00 0.50 0.06 -- 105.86 -61.00-150.00 52 12 \w -91.00 -23.00 0.50 0.05 -- -47.45 122.00 137.00 136 13 \w -58.00 -33.00 0.50 0.06 -- -105.86 77.00 -60.00 50 14 \w -106.00 -79.00 0.50 0.06 -- -105.86 77.00 -60.00 54 15 \w -126.00 -41.00 0.50 0.06 -- -105.86 149.00 -60.00 170 16 \w -70.00 -37.00 0.50 0.06 -- -105.86 61.00 120.00 66 17 \w -106.00 -37.00 0.50 0.06 -- -105.86 122.00 137.00 138 18 \w -169.00-143.00 0.50 0.06 -- -105.86 -61.00 -30.00 52 19 \w -129.00 -94.00 0.50 0.06 -- -105.86 -61.00 -30.00 70 20 \w -130.00-105.00 0.50 0.06 -- -105.86-122.00 56.00 50 21 \w -113.00 -62.00 0.50 0.05 -- -47.45-149.00-106.00 102 22 \w -110.00 -83.00 0.50 0.05 -- -47.45-125.00-180.00 54 23 \w -176.00-103.00 0.50 0.06 -- -105.86 -45.00 150.00 146 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Single source at home/near, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0985928000 _diffrn_orient_matrix_UB_12 0.0134801000 _diffrn_orient_matrix_UB_13 0.0407322000 _diffrn_orient_matrix_UB_21 0.0124773000 _diffrn_orient_matrix_UB_22 -0.1139403000 _diffrn_orient_matrix_UB_23 -0.0117532000 _diffrn_orient_matrix_UB_31 0.0080045000 _diffrn_orient_matrix_UB_32 0.0111129000 _diffrn_orient_matrix_UB_33 -0.1701933000 _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 0.0364 _diffrn_reflns_av_unetI/netI 0.0335 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.960 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 12692 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.960 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.674 _diffrn_reflns_theta_min 2.860 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.766 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.471 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.382 _exptl_crystal_description plate _exptl_crystal_F_000 792 _exptl_crystal_size_max 0.324 _exptl_crystal_size_mid 0.312 _exptl_crystal_size_min 0.163 _refine_diff_density_max 0.211 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.051 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 263 _refine_ls_number_reflns 3697 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.093 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0395 _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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1310 _refine_ls_wR_factor_ref 0.1355 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3337 _reflns_number_total 3697 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1py01088c1.cif _cod_data_source_block galukh336_corr _cod_database_code 1564903 _shelx_shelxl_version_number 2016/6 _chemical_oxdiff_formula C23H15N3O3 _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 100.00 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _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.a Aromatic/amide H refined with riding coordinates: C8(H8), C13(H13), C7(H7), C4(H4), C14(H14), C26(H26), C5(H5), C17(H17), C25(H25), C23(H23), C22(H22), C16(H16) 2.b Idealised Me refined as rotating group: C1(H1A,H1B,H1C) ; _shelx_res_file ; TITL galukh336_corr_a.res in P2(1)/c galukh336_corr.res created by SHELXL-2016/6 at 11:39:13 on 02-Nov-2020 REM Old TITL Galukh336_corr in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.120, Rweak 0.036, Alpha 0.016, Orientation as input REM Formula found by SHELXT: C23 N3 O3 CELL 1.54184 15.6119 13.3664 8.8742 90 98.224 90 ZERR 4 0.0002 0.0002 0.0001 0 0.001 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 92 60 12 12 L.S. 4 0 0 PLAN 5 CONF BOND $H list 4 fmap 2 53 MORE -1 ACTA REM REM REM WGHT 0.100000 FVAR 0.63920 O9 4 0.186458 0.828961 0.316967 11.00000 0.02650 0.01665 = 0.03156 0.00079 0.00028 0.00149 O18 4 0.554359 0.369575 0.941230 11.00000 0.01918 0.04313 = 0.02632 0.00120 -0.00057 0.00643 O27 4 -0.016660 0.201942 0.582868 11.00000 0.01980 0.02195 = 0.05281 0.00942 0.00744 -0.00053 N20 3 0.529419 0.360640 1.205893 11.00000 0.02997 0.03221 = 0.02920 -0.00185 -0.00260 -0.00222 N11 3 0.245853 0.971871 0.467628 11.00000 0.04191 0.02267 = 0.03227 0.00108 0.00938 -0.00320 C8 1 0.298543 0.608078 0.508891 11.00000 0.01722 0.02015 = 0.01931 -0.00014 0.00343 -0.00036 AFIX 43 H8 2 0.341777 0.592236 0.588667 11.00000 -1.20000 AFIX 0 C13 1 0.334639 0.403634 0.727542 11.00000 0.01676 0.01727 = 0.02424 -0.00041 0.00453 -0.00110 AFIX 43 H13 2 0.277549 0.410684 0.744626 11.00000 -1.20000 AFIX 0 C6 1 0.213095 0.729398 0.360319 11.00000 0.02016 0.01562 = 0.02486 0.00291 0.00698 0.00119 C7 1 0.277038 0.708433 0.478966 11.00000 0.01931 0.01790 = 0.02425 -0.00273 0.00442 -0.00293 AFIX 43 H7 2 0.305244 0.759430 0.537744 11.00000 -1.20000 AFIX 0 C21 1 0.198998 0.361463 0.478030 11.00000 0.01820 0.01825 = 0.01674 0.00118 0.00061 -0.00069 C12 1 0.352849 0.404840 0.578454 11.00000 0.01907 0.01278 = 0.02252 0.00042 0.00318 -0.00008 C2 1 0.279520 0.419962 0.444591 11.00000 0.01886 0.01656 = 0.01895 -0.00067 0.00362 -0.00030 C4 1 0.190825 0.557422 0.303147 11.00000 0.02147 0.01895 = 0.02203 -0.00200 0.00099 -0.00147 AFIX 43 H4 2 0.161650 0.507046 0.244376 11.00000 -1.20000 AFIX 0 C10 1 0.219900 0.902531 0.399750 11.00000 0.02394 0.01872 = 0.02742 0.00366 0.00787 0.00078 C14 1 0.399236 0.392202 0.851839 11.00000 0.02067 0.02005 = 0.01999 0.00055 0.00402 -0.00072 AFIX 43 H14 2 0.386296 0.391616 0.950927 11.00000 -1.20000 AFIX 0 C15 1 0.482945 0.381808 0.822416 11.00000 0.01762 0.02016 = 0.02480 0.00186 -0.00113 0.00180 C3 1 0.256411 0.531579 0.421450 11.00000 0.01757 0.01773 = 0.01958 -0.00025 0.00575 -0.00100 C26 1 0.132276 0.407535 0.541893 11.00000 0.02448 0.01645 = 0.02642 -0.00184 0.00584 -0.00062 AFIX 43 H26 2 0.135127 0.475949 0.561038 11.00000 -1.20000 AFIX 0 C5 1 0.168471 0.656134 0.271758 11.00000 0.02071 0.02267 = 0.02244 0.00068 0.00038 0.00132 AFIX 43 H5 2 0.124671 0.672666 0.193307 11.00000 -1.20000 AFIX 0 C24 1 0.058908 0.252930 0.547516 11.00000 0.01694 0.02150 = 0.02785 0.00462 0.00220 -0.00196 C17 1 0.439280 0.394924 0.555531 11.00000 0.02091 0.02107 = 0.02362 0.00091 0.00642 0.00147 AFIX 43 H17 2 0.453055 0.396060 0.456995 11.00000 -1.20000 AFIX 0 C1 1 0.307903 0.382720 0.294487 11.00000 0.02338 0.02080 = 0.02060 -0.00117 0.00419 0.00056 AFIX 137 H1A 2 0.331957 0.316750 0.309220 11.00000 -1.50000 H1B 2 0.350719 0.427300 0.264810 11.00000 -1.50000 H1C 2 0.258668 0.380971 0.216167 11.00000 -1.50000 AFIX 0 C25 1 0.061824 0.353532 0.577424 11.00000 0.02081 0.02246 = 0.03213 0.00103 0.00819 0.00253 AFIX 43 H25 2 0.017869 0.384782 0.620308 11.00000 -1.20000 AFIX 0 N29 3 -0.006745 0.031646 0.678411 11.00000 0.02576 0.03490 = 0.06946 0.02144 0.00628 -0.00040 C23 1 0.122211 0.203064 0.484350 11.00000 0.02465 0.01660 = 0.02978 -0.00173 0.00214 -0.00177 AFIX 43 H23 2 0.118254 0.134739 0.464802 11.00000 -1.20000 AFIX 0 C22 1 0.192416 0.258835 0.450827 11.00000 0.02143 0.01949 = 0.02616 -0.00140 0.00453 0.00125 AFIX 43 H22 2 0.236278 0.226621 0.408989 11.00000 -1.20000 AFIX 0 C28 1 -0.007976 0.111552 0.633483 11.00000 0.01817 0.02542 = 0.03283 0.00391 0.00205 -0.00233 C16 1 0.504872 0.383397 0.677904 11.00000 0.01714 0.02436 = 0.02982 0.00095 0.00546 0.00236 AFIX 43 H16 2 0.562260 0.376913 0.662295 11.00000 -1.20000 AFIX 0 C19 1 0.538632 0.365058 1.080096 11.00000 0.02197 0.02076 = 0.02768 -0.00074 -0.00346 0.00149 HKLF 4 REM galukh336_corr_a.res in P2(1)/c REM R1 = 0.0395 for 3337 Fo > 4sig(Fo) and 0.0428 for all 3697 data REM 263 parameters refined using 0 restraints END WGHT 0.0591 0.4410 REM Highest difference peak 0.211, deepest hole -0.247, 1-sigma level 0.051 Q1 1 0.2654 0.4737 0.4385 11.00000 0.05 0.21 Q2 1 0.0557 0.2992 0.5387 11.00000 0.05 0.17 Q3 1 0.1857 0.6130 0.2806 11.00000 0.05 0.16 Q4 1 0.2421 0.3962 0.4642 11.00000 0.05 0.16 Q5 1 0.2792 0.5652 0.4521 11.00000 0.05 0.15 ; _shelx_res_checksum 78931 _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 1.318 _oxdiff_exptl_absorpt_empirical_full_min 0.744 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 O9 O 0.18646(6) 0.82896(6) 0.31697(10) 0.0253(2) Uani 1 1 d . . . . . O18 O 0.55436(6) 0.36958(7) 0.94123(10) 0.0299(2) Uani 1 1 d . . . . . O27 O -0.01666(6) 0.20194(6) 0.58287(12) 0.0313(2) Uani 1 1 d . . . . . N20 N 0.52942(8) 0.36064(9) 1.20589(13) 0.0311(3) Uani 1 1 d . . . . . N11 N 0.24585(8) 0.97187(8) 0.46763(13) 0.0319(3) Uani 1 1 d . . . . . C8 C 0.29854(7) 0.60808(8) 0.50889(12) 0.0188(2) Uani 1 1 d . . . . . H8 H 0.341777 0.592236 0.588667 0.023 Uiso 1 1 calc R U . . . C13 C 0.33464(7) 0.40363(8) 0.72754(13) 0.0193(3) Uani 1 1 d . . . . . H13 H 0.277549 0.410684 0.744626 0.023 Uiso 1 1 calc R U . . . C6 C 0.21310(7) 0.72940(8) 0.36032(13) 0.0198(3) Uani 1 1 d . . . . . C7 C 0.27704(7) 0.70843(8) 0.47897(13) 0.0204(3) Uani 1 1 d . . . . . H7 H 0.305244 0.759430 0.537744 0.024 Uiso 1 1 calc R U . . . C21 C 0.19900(7) 0.36146(8) 0.47803(12) 0.0179(2) Uani 1 1 d . . . . . C12 C 0.35285(7) 0.40484(8) 0.57845(13) 0.0181(2) Uani 1 1 d . . . . . C2 C 0.27952(7) 0.41996(8) 0.44459(12) 0.0180(2) Uani 1 1 d . . . . . C4 C 0.19083(7) 0.55742(9) 0.30315(12) 0.0210(3) Uani 1 1 d . . . . . H4 H 0.161650 0.507046 0.244376 0.025 Uiso 1 1 calc R U . . . C10 C 0.21990(8) 0.90253(8) 0.39975(14) 0.0229(3) Uani 1 1 d . . . . . C14 C 0.39924(7) 0.39220(8) 0.85184(13) 0.0201(3) Uani 1 1 d . . . . . H14 H 0.386296 0.391616 0.950927 0.024 Uiso 1 1 calc R U . . . C15 C 0.48295(8) 0.38181(8) 0.82242(13) 0.0213(3) Uani 1 1 d . . . . . C3 C 0.25641(7) 0.53158(8) 0.42145(12) 0.0180(2) Uani 1 1 d . . . . . C26 C 0.13228(8) 0.40754(8) 0.54189(13) 0.0222(3) Uani 1 1 d . . . . . H26 H 0.135127 0.475949 0.561038 0.027 Uiso 1 1 calc R U . . . C5 C 0.16847(8) 0.65613(9) 0.27176(13) 0.0222(3) Uani 1 1 d . . . . . H5 H 0.124671 0.672666 0.193307 0.027 Uiso 1 1 calc R U . . . C24 C 0.05891(7) 0.25293(9) 0.54752(13) 0.0222(3) Uani 1 1 d . . . . . C17 C 0.43928(8) 0.39492(8) 0.55553(14) 0.0216(3) Uani 1 1 d . . . . . H17 H 0.453055 0.396060 0.456995 0.026 Uiso 1 1 calc R U . . . C1 C 0.30790(8) 0.38272(8) 0.29449(13) 0.0215(3) Uani 1 1 d . . . . . H1A H 0.331957 0.316750 0.309220 0.032 Uiso 1 1 calc R U . . . H1B H 0.350719 0.427300 0.264810 0.032 Uiso 1 1 calc R U . . . H1C H 0.258668 0.380971 0.216167 0.032 Uiso 1 1 calc R U . . . C25 C 0.06182(8) 0.35353(9) 0.57742(14) 0.0247(3) Uani 1 1 d . . . . . H25 H 0.017869 0.384782 0.620308 0.030 Uiso 1 1 calc R U . . . N29 N -0.00674(8) 0.03165(9) 0.67841(17) 0.0434(3) Uani 1 1 d . . . . . C23 C 0.12221(8) 0.20306(8) 0.48435(14) 0.0238(3) Uani 1 1 d . . . . . H23 H 0.118254 0.134739 0.464802 0.029 Uiso 1 1 calc R U . . . C22 C 0.19242(8) 0.25884(9) 0.45083(13) 0.0223(3) Uani 1 1 d . . . . . H22 H 0.236278 0.226621 0.408989 0.027 Uiso 1 1 calc R U . . . C28 C -0.00798(8) 0.11155(9) 0.63348(15) 0.0256(3) Uani 1 1 d . . . . . C16 C 0.50487(8) 0.38340(9) 0.67790(14) 0.0236(3) Uani 1 1 d . . . . . H16 H 0.562260 0.376913 0.662295 0.028 Uiso 1 1 calc R U . . . C19 C 0.53863(8) 0.36506(9) 1.08010(14) 0.0242(3) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O9 0.0265(5) 0.0167(4) 0.0316(5) 0.0008(3) 0.0003(4) 0.0015(3) O18 0.0192(4) 0.0431(6) 0.0263(5) 0.0012(4) -0.0006(3) 0.0064(4) O27 0.0198(4) 0.0220(5) 0.0528(6) 0.0094(4) 0.0074(4) -0.0005(3) N20 0.0300(6) 0.0322(6) 0.0292(6) -0.0019(4) -0.0026(5) -0.0022(5) N11 0.0419(7) 0.0227(6) 0.0323(6) 0.0011(4) 0.0094(5) -0.0032(5) C8 0.0172(5) 0.0202(6) 0.0193(5) -0.0001(4) 0.0034(4) -0.0004(4) C13 0.0168(5) 0.0173(5) 0.0242(6) -0.0004(4) 0.0045(4) -0.0011(4) C6 0.0202(5) 0.0156(6) 0.0249(5) 0.0029(4) 0.0070(4) 0.0012(4) C7 0.0193(5) 0.0179(5) 0.0243(5) -0.0027(4) 0.0044(4) -0.0029(4) C21 0.0182(5) 0.0182(6) 0.0167(5) 0.0012(4) 0.0006(4) -0.0007(4) C12 0.0191(5) 0.0128(5) 0.0225(6) 0.0004(4) 0.0032(4) -0.0001(4) C2 0.0189(5) 0.0166(5) 0.0190(5) -0.0007(4) 0.0036(4) -0.0003(4) C4 0.0215(6) 0.0190(6) 0.0220(5) -0.0020(4) 0.0010(4) -0.0015(4) C10 0.0239(6) 0.0187(6) 0.0274(6) 0.0037(4) 0.0079(5) 0.0008(4) C14 0.0207(6) 0.0200(5) 0.0200(6) 0.0006(4) 0.0040(4) -0.0007(4) C15 0.0176(5) 0.0202(5) 0.0248(6) 0.0019(4) -0.0011(4) 0.0018(4) C3 0.0176(5) 0.0177(5) 0.0196(5) -0.0002(4) 0.0058(4) -0.0010(4) C26 0.0245(6) 0.0164(6) 0.0264(6) -0.0018(4) 0.0058(5) -0.0006(4) C5 0.0207(6) 0.0227(6) 0.0224(6) 0.0007(4) 0.0004(4) 0.0013(4) C24 0.0169(5) 0.0215(6) 0.0279(6) 0.0046(4) 0.0022(4) -0.0020(4) C17 0.0209(6) 0.0211(6) 0.0236(6) 0.0009(4) 0.0064(4) 0.0015(4) C1 0.0234(6) 0.0208(5) 0.0206(6) -0.0012(4) 0.0042(4) 0.0006(4) C25 0.0208(6) 0.0225(6) 0.0321(6) 0.0010(5) 0.0082(5) 0.0025(4) N29 0.0258(6) 0.0349(7) 0.0695(9) 0.0214(6) 0.0063(6) -0.0004(5) C23 0.0246(6) 0.0166(5) 0.0298(6) -0.0017(4) 0.0021(5) -0.0018(4) C22 0.0214(6) 0.0195(6) 0.0262(6) -0.0014(4) 0.0045(4) 0.0012(4) C28 0.0182(6) 0.0254(6) 0.0328(7) 0.0039(5) 0.0021(5) -0.0023(4) C16 0.0171(6) 0.0244(6) 0.0298(6) 0.0010(5) 0.0055(5) 0.0024(4) C19 0.0220(6) 0.0208(6) 0.0277(7) -0.0007(4) -0.0035(5) 0.0015(4) 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' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 0 0 0.0683 1 0 0 0.0945 -2 0 1 0.0986 2 0 -1 0.1105 0 0 -1 0.1601 0 0 1 0.1506 2 1 -1 0.1299 2 1 2 0.1615 1 1 0 0.1346 -2 -2 1 0.1425 -1 -2 -2 0.1503 1 1 -1 0.1421 1 2 2 0.1747 -1 -2 0 0.1578 0 1 -1 0.1432 -1 2 0 0.1355 1 -2 0 0.1476 1 -1 -1 0.1374 2 -1 0 0.1007 -2 1 0 0.1016 -1 1 -2 0.1372 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 C10 O9 C6 118.48(9) . . ? C19 O18 C15 118.30(10) . . ? C28 O27 C24 118.18(9) . . ? C7 C8 H8 119.4 . . ? C3 C8 H8 119.4 . . ? C3 C8 C7 121.17(10) . . ? C12 C13 H13 119.0 . . ? C14 C13 H13 119.0 . . ? C14 C13 C12 122.06(10) . . ? C7 C6 O9 123.23(10) . . ? C7 C6 C5 122.99(10) . . ? C5 C6 O9 113.78(10) . . ? C8 C7 H7 121.0 . . ? C6 C7 C8 118.03(10) . . ? C6 C7 H7 121.0 . . ? C26 C21 C2 121.93(10) . . ? C22 C21 C2 120.44(10) . . ? C22 C21 C26 117.57(10) . . ? C13 C12 C2 120.26(10) . . ? C13 C12 C17 117.98(10) . . ? C17 C12 C2 121.73(10) . . ? C21 C2 C1 110.13(9) . . ? C12 C2 C21 108.71(8) . . ? C12 C2 C3 111.32(9) . . ? C12 C2 C1 110.45(9) . . ? C3 C2 C21 109.51(9) . . ? C3 C2 C1 106.70(9) . . ? C3 C4 H4 119.2 . . ? C5 C4 H4 119.2 . . ? C5 C4 C3 121.50(10) . . ? N11 C10 O9 175.55(13) . . ? C13 C14 H14 121.3 . . ? C15 C14 C13 117.43(11) . . ? C15 C14 H14 121.3 . . ? C14 C15 O18 122.22(11) . . ? C16 C15 O18 114.70(10) . . ? C16 C15 C14 123.08(11) . . ? C8 C3 C2 123.65(10) . . ? C8 C3 C4 118.26(10) . . ? C4 C3 C2 118.06(10) . . ? C21 C26 H26 119.2 . . ? C25 C26 C21 121.55(10) . . ? C25 C26 H26 119.2 . . ? C6 C5 C4 118.03(11) . . ? C6 C5 H5 121.0 . . ? C4 C5 H5 121.0 . . ? C25 C24 O27 115.42(10) . . ? C25 C24 C23 123.26(11) . . ? C23 C24 O27 121.31(10) . . ? C12 C17 H17 119.5 . . ? C16 C17 C12 120.98(11) . . ? C16 C17 H17 119.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C26 C25 H25 120.9 . . ? C24 C25 C26 118.13(11) . . ? C24 C25 H25 120.9 . . ? C24 C23 H23 121.3 . . ? C24 C23 C22 117.44(10) . . ? C22 C23 H23 121.3 . . ? C21 C22 H22 119.0 . . ? C23 C22 C21 122.05(11) . . ? C23 C22 H22 119.0 . . ? N29 C28 O27 174.93(13) . . ? C15 C16 C17 118.47(11) . . ? C15 C16 H16 120.8 . . ? C17 C16 H16 120.8 . . ? N20 C19 O18 176.28(12) . . ? 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 O9 C6 1.4305(13) . ? O9 C10 1.2921(15) . ? O18 C15 1.4301(14) . ? O18 C19 1.2919(16) . ? O27 C24 1.4355(14) . ? O27 C28 1.2894(15) . ? N20 C19 1.1473(17) . ? N11 C10 1.1472(16) . ? C8 H8 0.9300 . ? C8 C7 1.3990(16) . ? C8 C3 1.3908(15) . ? C13 H13 0.9300 . ? C13 C12 1.3925(16) . ? C13 C14 1.3924(16) . ? C6 C7 1.3722(16) . ? C6 C5 1.3803(16) . ? C7 H7 0.9300 . ? C21 C2 1.5448(15) . ? C21 C26 1.3980(16) . ? C21 C22 1.3941(16) . ? C12 C2 1.5406(15) . ? C12 C17 1.3994(17) . ? C2 C3 1.5417(15) . ? C2 C1 1.5451(15) . ? C4 H4 0.9300 . ? C4 C3 1.4008(15) . ? C4 C5 1.3829(16) . ? C14 H14 0.9300 . ? C14 C15 1.3759(17) . ? C15 C16 1.3740(18) . ? C26 H26 0.9300 . ? C26 C25 1.3891(16) . ? C5 H5 0.9300 . ? C24 C25 1.3701(17) . ? C24 C23 1.3761(17) . ? C17 H17 0.9300 . ? C17 C16 1.3905(17) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C25 H25 0.9300 . ? N29 C28 1.1392(17) . ? C23 H23 0.9300 . ? C23 C22 1.3924(16) . ? C22 H22 0.9300 . ? C16 H16 0.9300 . ? 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 O9 C6 C7 C8 -178.88(10) . . . . ? O9 C6 C5 C4 178.79(10) . . . . ? O18 C15 C16 C17 179.94(10) . . . . ? O27 C24 C25 C26 -178.34(10) . . . . ? O27 C24 C23 C22 178.69(10) . . . . ? C13 C12 C2 C21 -39.38(13) . . . . ? C13 C12 C2 C3 81.34(12) . . . . ? C13 C12 C2 C1 -160.31(10) . . . . ? C13 C12 C17 C16 0.52(17) . . . . ? C13 C14 C15 O18 -179.98(10) . . . . ? C13 C14 C15 C16 0.75(17) . . . . ? C7 C8 C3 C2 177.51(10) . . . . ? C7 C8 C3 C4 -0.76(16) . . . . ? C7 C6 C5 C4 -1.25(17) . . . . ? C21 C2 C3 C8 121.74(11) . . . . ? C21 C2 C3 C4 -59.99(12) . . . . ? C21 C26 C25 C24 -0.29(18) . . . . ? C12 C13 C14 C15 -0.10(16) . . . . ? C12 C2 C3 C8 1.50(14) . . . . ? C12 C2 C3 C4 179.77(9) . . . . ? C12 C17 C16 C15 0.08(17) . . . . ? C2 C21 C26 C25 -177.29(11) . . . . ? C2 C21 C22 C23 177.80(10) . . . . ? C2 C12 C17 C16 178.65(10) . . . . ? C10 O9 C6 C7 -4.94(16) . . . . ? C10 O9 C6 C5 175.03(10) . . . . ? C14 C13 C12 C2 -178.68(10) . . . . ? C14 C13 C12 C17 -0.51(16) . . . . ? C14 C15 C16 C17 -0.75(18) . . . . ? C3 C8 C7 C6 -0.12(16) . . . . ? C3 C4 C5 C6 0.29(17) . . . . ? C26 C21 C2 C12 96.44(12) . . . . ? C26 C21 C2 C3 -25.39(13) . . . . ? C26 C21 C2 C1 -142.43(11) . . . . ? C26 C21 C22 C23 0.40(17) . . . . ? C5 C6 C7 C8 1.16(17) . . . . ? C5 C4 C3 C8 0.67(16) . . . . ? C5 C4 C3 C2 -177.70(10) . . . . ? C24 C23 C22 C21 -0.62(18) . . . . ? C17 C12 C2 C21 142.53(10) . . . . ? C17 C12 C2 C3 -96.76(12) . . . . ? C17 C12 C2 C1 21.59(14) . . . . ? C1 C2 C3 C8 -119.08(11) . . . . ? C1 C2 C3 C4 59.19(12) . . . . ? C25 C24 C23 C22 0.39(18) . . . . ? C23 C24 C25 C26 0.05(18) . . . . ? C22 C21 C2 C12 -80.85(12) . . . . ? C22 C21 C2 C3 157.33(10) . . . . ? C22 C21 C2 C1 40.28(13) . . . . ? C22 C21 C26 C25 0.07(16) . . . . ? C28 O27 C24 C25 -144.80(12) . . . . ? C28 O27 C24 C23 36.78(16) . . . . ? C19 O18 C15 C14 2.24(16) . . . . ? C19 O18 C15 C16 -178.44(10) . . . . ? loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -0.9986 -0.0011 -0.0001 -0.0985 -0.0123 -0.0080 0.9986 0.0011 0.0001 0.0985 0.0123 0.0080 -1.9962 -0.0013 0.9994 -0.1561 -0.0365 -0.1861 1.9962 0.0013 -0.9994 0.1561 0.0365 0.1861 -0.0010 -0.0008 -0.9996 -0.0408 0.0118 0.1701 0.0010 0.0008 0.9996 0.0408 -0.0118 -0.1701 1.9964 1.0008 -0.9997 0.1696 -0.0774 0.1972 1.9995 1.0033 1.9992 0.2921 -0.1129 -0.3131 0.9988 1.0006 -0.0001 0.1120 -0.1015 0.0191 -1.9966 -2.0003 0.9999 -0.1831 0.1913 -0.2084 -1.0011 -2.0018 -1.9989 -0.2071 0.2391 0.3099 0.9978 0.9998 -0.9998 0.0711 -0.0897 0.1893 1.0011 2.0018 1.9989 0.2071 -0.2391 -0.3099 -0.9990 -2.0001 0.0004 -0.1254 0.2154 -0.0303 -0.0009 0.9987 -0.9999 -0.0274 -0.1021 0.1813 -0.9983 1.9980 -0.0006 -0.0715 -0.2401 0.0143 0.9983 -1.9980 0.0006 0.0715 0.2401 -0.0143 0.9974 -0.9993 -0.9993 0.0442 0.1381 0.1670 1.9971 -0.9974 0.0004 0.1835 0.1386 0.0048 -1.9971 0.9974 -0.0004 -0.1835 -0.1386 -0.0048 -1.0006 0.9968 -1.9996 -0.1667 -0.1026 0.3434